# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Jurg Hulliger' 'Norwid Behrnd' 'H Burgi' 'Gael Labat' 'P Venugopalan' _publ_contact_author_name 'Jurg Hulliger' _publ_contact_author_email JUERG.HULLIGER@IAC.UNIBE.CH _publ_section_title ; Influence of the solvent of crystallization on the orientational disorder of (trans)-4-chloro-4'-nitrostilbene ; # Attachment 'Behrndnr-CIF-CNS.txt' data_CNS-ClBzI-small-P21_c _database_code_depnum_ccdc_archive 'CCDC 761200' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9200(3) _cell_length_b 12.9790(10) _cell_length_c 12.2368(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.153(3) _cell_angle_gamma 90.00 _cell_volume 621.64(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3492 _cell_measurement_theta_min 3.139 _cell_measurement_theta_max 25.132 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.475985 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3459 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.78 _reflns_number_total 2463 _reflns_number_gt 1060 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+0.3558P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 2463 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1675 _refine_ls_R_factor_gt 0.0722 _refine_ls_wR_factor_ref 0.1794 _refine_ls_wR_factor_gt 0.1523 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.376(2) -0.4600(3) -0.1755(9) 0.126(3) Uani 0.50 1 d P . . N11 N 0.352(5) -0.4213(11) -0.1713(16) 0.079(3) Uani 0.50 1 d P . . O11 O 0.309(3) -0.4958(10) -0.1230(8) 0.141(4) Uani 0.50 1 d P . . O12 O 0.5011(15) -0.4128(4) -0.2586(5) 0.114(2) Uani 0.50 1 d P . . C1 C 0.2613(7) -0.3286(2) -0.1238(3) 0.0709(8) Uani 1 1 d . . . C2 C 0.3159(7) -0.2385(3) -0.1788(2) 0.0823(9) Uani 1 1 d . . . H2A H 0.4153 -0.2398 -0.2461 0.099 Uiso 1 1 calc R . . C3 C 0.2236(7) -0.1474(2) -0.1344(2) 0.0763(9) Uani 1 1 d . . . H3A H 0.2572 -0.0865 -0.1724 0.092 Uiso 1 1 calc R . . C4 C 0.0784(6) -0.1437(2) -0.0322(2) 0.0670(8) Uani 1 1 d . . . C5 C 0.0287(7) -0.2353(2) 0.0205(2) 0.0738(8) Uani 1 1 d . . . H5A H -0.0694 -0.2341 0.0880 0.089 Uiso 1 1 calc R . . C6 C 0.1188(7) -0.3298(2) -0.0227(2) 0.0772(9) Uani 1 1 d . . . H6A H 0.0849 -0.3911 0.0145 0.093 Uiso 1 1 calc R . . C7 C -0.0243(7) -0.04656(18) 0.0186(2) 0.0752(8) Uani 1 1 d . . . H7A H -0.1349 -0.0519 0.0837 0.090 Uiso 1 1 calc R . . Cl11 Cl -0.376(2) 0.4600(3) 0.1755(9) 0.126(3) Uani 0.50 1 d P . . N1 N -0.352(5) 0.4213(11) 0.1713(16) 0.079(3) Uani 0.50 1 d P . . O1 O -0.309(3) 0.4958(10) 0.1230(8) 0.141(4) Uani 0.50 1 d P . . O2 O -0.5011(15) 0.4128(4) 0.2586(5) 0.114(2) Uani 0.50 1 d P . . C11 C -0.2613(7) 0.3286(2) 0.1238(3) 0.0709(8) Uani 1 1 d . . . C12 C -0.3159(7) 0.2385(3) 0.1788(2) 0.0823(9) Uani 1 1 d . . . H12A H -0.4153 0.2398 0.2461 0.099 Uiso 1 1 calc R . . C13 C -0.2236(7) 0.1474(2) 0.1344(2) 0.0763(9) Uani 1 1 d . . . H13A H -0.2572 0.0865 0.1724 0.092 Uiso 1 1 calc R . . C14 C -0.0784(6) 0.1437(2) 0.0322(2) 0.0670(8) Uani 1 1 d . . . C15 C -0.0287(7) 0.2353(2) -0.0205(2) 0.0738(8) Uani 1 1 d . . . H15A H 0.0694 0.2341 -0.0880 0.089 Uiso 1 1 calc R . . C16 C -0.1188(7) 0.3298(2) 0.0227(2) 0.0772(9) Uani 1 1 d . . . H16A H -0.0849 0.3911 -0.0145 0.093 Uiso 1 1 calc R . . C17 C 0.0243(7) 0.04656(18) -0.0186(2) 0.0752(8) Uani 1 1 d . . . H17A H 0.1349 0.0519 -0.0837 0.090 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.120(3) 0.114(7) 0.144(5) -0.064(5) 0.002(3) 0.034(4) N11 0.069(5) 0.081(8) 0.089(9) 0.002(8) 0.020(5) 0.019(7) O11 0.187(8) 0.089(6) 0.151(8) -0.005(5) 0.045(6) 0.011(5) O12 0.155(5) 0.096(4) 0.094(4) -0.025(3) 0.036(4) 0.016(3) C1 0.0638(19) 0.075(2) 0.074(2) -0.0134(17) -0.0012(16) 0.0055(16) C2 0.073(2) 0.110(3) 0.064(2) -0.0038(19) 0.0108(16) 0.0002(19) C3 0.075(2) 0.081(2) 0.075(2) 0.0060(17) 0.0117(17) -0.0024(17) C4 0.0532(17) 0.079(2) 0.069(2) -0.0063(17) 0.0014(14) -0.0013(14) C5 0.074(2) 0.086(2) 0.0623(18) 0.0000(17) 0.0125(15) -0.0075(17) C6 0.081(2) 0.072(2) 0.079(2) 0.0018(17) 0.0037(17) 0.0041(16) C7 0.0696(19) 0.078(2) 0.078(2) 0.0062(17) 0.0055(15) -0.0025(17) Cl11 0.120(3) 0.114(7) 0.144(5) -0.064(5) 0.002(3) 0.034(4) N1 0.069(5) 0.081(8) 0.089(9) 0.002(8) 0.020(5) 0.019(7) O1 0.187(8) 0.089(6) 0.151(8) -0.005(5) 0.045(6) 0.011(5) O2 0.155(5) 0.096(4) 0.094(4) -0.025(3) 0.036(4) 0.016(3) C11 0.0638(19) 0.075(2) 0.074(2) -0.0134(17) -0.0012(16) 0.0055(16) C12 0.073(2) 0.110(3) 0.064(2) -0.0038(19) 0.0108(16) 0.0002(19) C13 0.075(2) 0.081(2) 0.075(2) 0.0060(17) 0.0117(17) -0.0024(17) C14 0.0532(17) 0.079(2) 0.069(2) -0.0063(17) 0.0014(14) -0.0013(14) C15 0.074(2) 0.086(2) 0.0623(18) 0.0000(17) 0.0125(15) -0.0075(17) C16 0.081(2) 0.072(2) 0.079(2) 0.0018(17) 0.0037(17) 0.0041(16) C17 0.0696(19) 0.078(2) 0.078(2) 0.0062(17) 0.0055(15) -0.0025(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.515(14) . ? Cl1 O11 0.847(12) . ? Cl1 O12 1.305(10) . ? Cl1 C1 1.883(5) . ? N11 O11 1.15(2) . ? N11 O12 1.250(18) . ? N11 C1 1.391(12) . ? C1 C2 1.372(4) . ? C1 C6 1.385(4) . ? C2 C3 1.359(4) . ? C2 H2A 0.9300 . ? C3 C4 1.403(4) . ? C3 H3A 0.9300 . ? C4 C5 1.372(3) . ? C4 C7 1.471(3) . ? C5 C6 1.389(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.309(5) . ? C7 H7A 0.9300 . ? Cl11 N1 0.515(14) . ? Cl11 O1 0.847(12) . ? Cl11 O2 1.305(10) . ? Cl11 C11 1.883(5) . ? N1 O1 1.15(2) . ? N1 O2 1.250(18) . ? N1 C11 1.391(12) . ? C11 C12 1.372(4) . ? C11 C16 1.385(4) . ? C12 C13 1.359(4) . ? C12 H12A 0.9300 . ? C13 C14 1.403(4) . ? C13 H13A 0.9300 . ? C14 C15 1.372(3) . ? C14 C17 1.471(3) . ? C15 C16 1.389(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 113(4) . . ? N11 Cl1 O12 72(3) . . ? O11 Cl1 O12 174.1(13) . . ? N11 Cl1 C1 15(3) . . ? O11 Cl1 C1 98.7(14) . . ? O12 Cl1 C1 86.8(4) . . ? Cl1 N11 O11 43(3) . . ? Cl1 N11 O12 84(3) . . ? O11 N11 O12 127.0(12) . . ? Cl1 N11 C1 160(4) . . ? O11 N11 C1 117.7(11) . . ? O12 N11 C1 115.0(12) . . ? Cl1 O11 N11 24.3(10) . . ? N11 O12 Cl1 23.1(6) . . ? C2 C1 N11 118.8(8) . . ? C2 C1 C6 121.9(3) . . ? N11 C1 C6 119.2(8) . . ? C2 C1 Cl1 124.1(4) . . ? N11 C1 Cl1 5.4(11) . . ? C6 C1 Cl1 114.0(4) . . ? C3 C2 C1 119.5(3) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C5 C4 C3 117.6(3) . . ? C5 C4 C7 119.7(3) . . ? C3 C4 C7 122.7(3) . . ? C4 C5 C6 122.7(3) . . ? C4 C5 H5A 118.6 . . ? C6 C5 H5A 118.6 . . ? C1 C6 C5 117.0(3) . . ? C1 C6 H6A 121.5 . . ? C5 C6 H6A 121.5 . . ? C17 C7 C4 126.6(4) . . ? C17 C7 H7A 116.7 . . ? C4 C7 H7A 116.7 . . ? N1 Cl11 O1 113(4) . . ? N1 Cl11 O2 72(3) . . ? O1 Cl11 O2 174.1(13) . . ? N1 Cl11 C11 15(3) . . ? O1 Cl11 C11 98.7(14) . . ? O2 Cl11 C11 86.8(4) . . ? Cl11 N1 O1 43(3) . . ? Cl11 N1 O2 84(3) . . ? O1 N1 O2 127.0(12) . . ? Cl11 N1 C11 160(4) . . ? O1 N1 C11 117.7(11) . . ? O2 N1 C11 115.0(12) . . ? Cl11 O1 N1 24.3(10) . . ? N1 O2 Cl11 23.1(6) . . ? C12 C11 N1 118.8(8) . . ? C12 C11 C16 121.9(3) . . ? N1 C11 C16 119.2(8) . . ? C12 C11 Cl11 124.1(4) . . ? N1 C11 Cl11 5.4(11) . . ? C16 C11 Cl11 114.0(4) . . ? C13 C12 C11 119.5(3) . . ? C13 C12 H12A 120.2 . . ? C11 C12 H12A 120.2 . . ? C12 C13 C14 121.1(3) . . ? C12 C13 H13A 119.4 . . ? C14 C13 H13A 119.4 . . ? C15 C14 C13 117.6(3) . . ? C15 C14 C17 119.7(3) . . ? C13 C14 C17 122.7(3) . . ? C14 C15 C16 122.7(3) . . ? C14 C15 H15A 118.6 . . ? C16 C15 H15A 118.6 . . ? C11 C16 C15 117.0(3) . . ? C11 C16 H16A 121.5 . . ? C15 C16 H16A 121.5 . . ? C7 C17 C14 126.6(4) . . ? C7 C17 H17A 116.7 . . ? C14 C17 H17A 116.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 Cl1 N11 O11 -178(2) . . . . ? C1 Cl1 N11 O11 -11(14) . . . . ? O11 Cl1 N11 O12 178(2) . . . . ? C1 Cl1 N11 O12 166(12) . . . . ? O11 Cl1 N11 C1 11(14) . . . . ? O12 Cl1 N11 C1 -166(12) . . . . ? O12 Cl1 O11 N11 160(19) . . . . ? C1 Cl1 O11 N11 3(4) . . . . ? O12 N11 O11 Cl1 -3(3) . . . . ? C1 N11 O11 Cl1 -176(5) . . . . ? O11 N11 O12 Cl1 1.8(17) . . . . ? C1 N11 O12 Cl1 175(5) . . . . ? O11 Cl1 O12 N11 -161(18) . . . . ? C1 Cl1 O12 N11 -3(3) . . . . ? Cl1 N11 C1 C2 170(11) . . . . ? O11 N11 C1 C2 178.8(14) . . . . ? O12 N11 C1 C2 5.0(19) . . . . ? Cl1 N11 C1 C6 -10(12) . . . . ? O11 N11 C1 C6 -1(2) . . . . ? O12 N11 C1 C6 -175.1(10) . . . . ? O11 N11 C1 Cl1 9(10) . . . . ? O12 N11 C1 Cl1 -165(13) . . . . ? N11 Cl1 C1 C2 -11(12) . . . . ? O11 Cl1 C1 C2 -179.8(11) . . . . ? O12 Cl1 C1 C2 2.4(8) . . . . ? O11 Cl1 C1 N11 -169(13) . . . . ? O12 Cl1 C1 N11 13(11) . . . . ? N11 Cl1 C1 C6 170(12) . . . . ? O11 Cl1 C1 C6 1.1(14) . . . . ? O12 Cl1 C1 C6 -176.6(5) . . . . ? N11 C1 C2 C3 178.9(10) . . . . ? C6 C1 C2 C3 -1.0(4) . . . . ? Cl1 C1 C2 C3 -180.0(4) . . . . ? C1 C2 C3 C4 1.1(4) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C2 C3 C4 C7 179.9(3) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C7 C4 C5 C6 179.9(3) . . . . ? C2 C1 C6 C5 0.7(4) . . . . ? N11 C1 C6 C5 -179.2(10) . . . . ? Cl1 C1 C6 C5 179.8(4) . . . . ? C4 C5 C6 C1 -0.6(4) . . . . ? C5 C4 C7 C17 175.8(4) . . . . ? C3 C4 C7 C17 -5.0(5) . . . . ? O2 Cl11 N1 O1 178(2) . . . . ? C11 Cl11 N1 O1 11(14) . . . . ? O1 Cl11 N1 O2 -178(2) . . . . ? C11 Cl11 N1 O2 -166(12) . . . . ? O1 Cl11 N1 C11 -11(14) . . . . ? O2 Cl11 N1 C11 166(12) . . . . ? O2 Cl11 O1 N1 -160(19) . . . . ? C11 Cl11 O1 N1 -3(4) . . . . ? O2 N1 O1 Cl11 3(3) . . . . ? C11 N1 O1 Cl11 176(5) . . . . ? O1 N1 O2 Cl11 -1.8(17) . . . . ? C11 N1 O2 Cl11 -175(5) . . . . ? O1 Cl11 O2 N1 161(18) . . . . ? C11 Cl11 O2 N1 3(3) . . . . ? Cl11 N1 C11 C12 -170(11) . . . . ? O1 N1 C11 C12 -178.8(14) . . . . ? O2 N1 C11 C12 -5.0(19) . . . . ? Cl11 N1 C11 C16 10(12) . . . . ? O1 N1 C11 C16 1(2) . . . . ? O2 N1 C11 C16 175.1(10) . . . . ? O1 N1 C11 Cl11 -9(10) . . . . ? O2 N1 C11 Cl11 165(13) . . . . ? N1 Cl11 C11 C12 11(12) . . . . ? O1 Cl11 C11 C12 179.8(11) . . . . ? O2 Cl11 C11 C12 -2.4(8) . . . . ? O1 Cl11 C11 N1 169(13) . . . . ? O2 Cl11 C11 N1 -13(11) . . . . ? N1 Cl11 C11 C16 -170(12) . . . . ? O1 Cl11 C11 C16 -1.1(14) . . . . ? O2 Cl11 C11 C16 176.6(5) . . . . ? N1 C11 C12 C13 -178.9(10) . . . . ? C16 C11 C12 C13 1.0(4) . . . . ? Cl11 C11 C12 C13 180.0(4) . . . . ? C11 C12 C13 C14 -1.1(4) . . . . ? C12 C13 C14 C15 0.9(4) . . . . ? C12 C13 C14 C17 -179.9(3) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? C17 C14 C15 C16 -179.9(3) . . . . ? C12 C11 C16 C15 -0.7(4) . . . . ? N1 C11 C16 C15 179.2(10) . . . . ? Cl11 C11 C16 C15 -179.8(4) . . . . ? C14 C15 C16 C11 0.6(4) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.8(4) . . . . ? C13 C14 C17 C7 5.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 27.78 _diffrn_measured_fraction_theta_full 0.871 _refine_diff_density_max 0.117 _refine_diff_density_min -0.099 _refine_diff_density_rms 0.031 # start Validation Reply Form _vrf_ABSTM02_CNS-ClBzI-small-P21_c ; PROBLEM: The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; _vrf_SYMMG02_CNS-ClBzI-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-ClBzI-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.87 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; _vrf_PLAT061_CNS-ClBzI-small-P21_c ; PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.49 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; # end Validation Reply Form #===END data_CNS-ClBzI-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761201' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9200(3) _cell_length_b 12.9790(10) _cell_length_c 12.2368(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.153(3) _cell_angle_gamma 90.00 _cell_volume 621.64(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3492 _cell_measurement_theta_min 3.139 _cell_measurement_theta_max 25.132 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.475985 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3459 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.78 _reflns_number_total 2463 _reflns_number_gt 1060 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+0.3558P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(3) _refine_ls_number_reflns 2463 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1534 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1467 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3648(12) -0.4593(2) -0.1758(4) 0.1150(17) Uani 0.360(4) 1 d P . . N11 N 0.380(3) -0.4174(7) -0.1710(10) 0.092(3) Uani 0.640(4) 1 d P . . O11 O 0.308(2) -0.4980(4) -0.1248(5) 0.127(3) Uani 0.640(4) 1 d P . . O12 O 0.5017(12) -0.4132(3) -0.2587(4) 0.1103(15) Uani 0.640(4) 1 d P . . C1 C 0.2620(6) -0.3288(2) -0.1236(2) 0.0724(7) Uani 1 1 d . . . C2 C 0.3163(6) -0.2386(2) -0.1792(2) 0.0796(7) Uani 1 1 d . . . H2A H 0.4150 -0.2399 -0.2466 0.096 Uiso 1 1 calc R . . C3 C 0.2236(6) -0.14724(19) -0.1343(2) 0.0775(7) Uani 1 1 d . . . H3A H 0.2577 -0.0864 -0.1723 0.093 Uiso 1 1 calc R . . C4 C 0.0785(5) -0.14304(19) -0.03262(19) 0.0654(6) Uani 1 1 d . . . C5 C 0.0289(6) -0.23572(18) 0.0206(2) 0.0737(7) Uani 1 1 d . . . H5A H -0.0691 -0.2347 0.0881 0.088 Uiso 1 1 calc R . . C6 C 0.1195(6) -0.32956(18) -0.0228(2) 0.0774(8) Uani 1 1 d . . . H6A H 0.0859 -0.3909 0.0145 0.093 Uiso 1 1 calc R . . C7 C -0.0240(6) -0.04633(15) 0.0182(2) 0.0743(7) Uani 1 1 d . . . H7A H -0.1347 -0.0519 0.0833 0.089 Uiso 1 1 calc R . . Cl11 Cl -0.3648(12) 0.4593(2) 0.1758(4) 0.1150(17) Uani 0.640(4) 1 d P . . N1 N -0.380(3) 0.4174(7) 0.1710(10) 0.092(3) Uani 0.360(4) 1 d P . . O1 O -0.308(2) 0.4980(4) 0.1248(5) 0.127(3) Uani 0.360(4) 1 d P . . O2 O -0.5017(12) 0.4132(3) 0.2587(4) 0.1103(15) Uani 0.360(4) 1 d P . . C11 C -0.2620(6) 0.3288(2) 0.1236(2) 0.0724(7) Uani 1 1 d . . . C12 C -0.3163(6) 0.2386(2) 0.1792(2) 0.0796(7) Uani 1 1 d . . . H12A H -0.4150 0.2399 0.2466 0.096 Uiso 1 1 calc R . . C13 C -0.2236(6) 0.14724(19) 0.1343(2) 0.0775(7) Uani 1 1 d . . . H13A H -0.2577 0.0864 0.1723 0.093 Uiso 1 1 calc R . . C14 C -0.0785(5) 0.14304(19) 0.03262(19) 0.0654(6) Uani 1 1 d . . . C15 C -0.0289(6) 0.23572(18) -0.0206(2) 0.0737(7) Uani 1 1 d . . . H15A H 0.0691 0.2347 -0.0881 0.088 Uiso 1 1 calc R . . C16 C -0.1195(6) 0.32956(18) 0.0228(2) 0.0774(8) Uani 1 1 d . . . H16A H -0.0859 0.3909 -0.0145 0.093 Uiso 1 1 calc R . . C17 C 0.0240(6) 0.04633(15) -0.0182(2) 0.0743(7) Uani 1 1 d . . . H17A H 0.1347 0.0519 -0.0833 0.089 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.111(2) 0.098(3) 0.137(3) -0.051(3) 0.0104(19) 0.011(3) N11 0.095(5) 0.073(6) 0.106(7) -0.011(5) -0.009(4) -0.016(5) O11 0.175(5) 0.066(3) 0.145(5) 0.008(3) 0.049(4) 0.011(3) O12 0.150(4) 0.091(3) 0.093(3) -0.022(3) 0.041(3) 0.016(3) C1 0.0618(16) 0.0795(18) 0.0752(18) -0.0156(15) -0.0014(13) 0.0046(14) C2 0.0737(17) 0.103(2) 0.0632(17) -0.0022(16) 0.0111(13) -0.0015(16) C3 0.0743(17) 0.0812(18) 0.0774(19) 0.0068(15) 0.0086(14) -0.0044(14) C4 0.0533(14) 0.0779(16) 0.0648(17) -0.0046(14) 0.0020(12) -0.0007(12) C5 0.0733(17) 0.0845(18) 0.0642(16) 0.0001(15) 0.0115(13) -0.0045(14) C6 0.0800(18) 0.0756(18) 0.077(2) 0.0022(14) 0.0050(15) 0.0024(14) C7 0.0690(15) 0.0791(17) 0.0751(17) 0.0059(15) 0.0067(13) -0.0025(15) Cl11 0.111(2) 0.098(3) 0.137(3) -0.051(3) 0.0104(19) 0.011(3) N1 0.095(5) 0.073(6) 0.106(7) -0.011(5) -0.009(4) -0.016(5) O1 0.175(5) 0.066(3) 0.145(5) 0.008(3) 0.049(4) 0.011(3) O2 0.150(4) 0.091(3) 0.093(3) -0.022(3) 0.041(3) 0.016(3) C11 0.0618(16) 0.0795(18) 0.0752(18) -0.0156(15) -0.0014(13) 0.0046(14) C12 0.0737(17) 0.103(2) 0.0632(17) -0.0022(16) 0.0111(13) -0.0015(16) C13 0.0743(17) 0.0812(18) 0.0774(19) 0.0068(15) 0.0086(14) -0.0044(14) C14 0.0533(14) 0.0779(16) 0.0648(17) -0.0046(14) 0.0020(12) -0.0007(12) C15 0.0733(17) 0.0845(18) 0.0642(16) 0.0001(15) 0.0115(13) -0.0045(14) C16 0.0800(18) 0.0756(18) 0.077(2) 0.0022(14) 0.0050(15) 0.0024(14) C17 0.0690(15) 0.0791(17) 0.0751(17) 0.0059(15) 0.0067(13) -0.0025(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.550(9) . ? Cl1 O11 0.840(6) . ? Cl1 O12 1.317(6) . ? Cl1 C1 1.862(3) . ? N11 O11 1.229(14) . ? N11 O12 1.198(12) . ? N11 C1 1.379(9) . ? C1 C2 1.377(3) . ? C1 C6 1.382(3) . ? C2 C3 1.364(3) . ? C2 H2A 0.9300 . ? C3 C4 1.398(3) . ? C3 H3A 0.9300 . ? C4 C5 1.386(3) . ? C4 C7 1.467(3) . ? C5 C6 1.383(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.300(4) . ? C7 H7A 0.9300 . ? Cl11 N1 0.550(9) . ? Cl11 O1 0.840(6) . ? Cl11 O2 1.317(6) . ? Cl11 C11 1.862(3) . ? N1 O1 1.229(14) . ? N1 O2 1.198(12) . ? N1 C11 1.379(9) . ? C11 C12 1.377(3) . ? C11 C16 1.382(3) . ? C12 C13 1.364(3) . ? C12 H12A 0.9300 . ? C13 C14 1.398(3) . ? C13 H13A 0.9300 . ? C14 C15 1.386(3) . ? C14 C17 1.467(3) . ? C15 C16 1.383(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 123(2) . . ? N11 Cl1 O12 65.5(16) . . ? O11 Cl1 O12 168.2(7) . . ? N11 Cl1 C1 24.3(15) . . ? O11 Cl1 C1 102.5(6) . . ? O12 Cl1 C1 87.4(3) . . ? Cl1 N11 O11 35.0(14) . . ? Cl1 N11 O12 89.8(16) . . ? O11 N11 O12 124.3(8) . . ? Cl1 N11 C1 146(2) . . ? O11 N11 C1 115.1(9) . . ? O12 N11 C1 119.8(9) . . ? Cl1 O11 N11 22.1(6) . . ? N11 O12 Cl1 24.7(4) . . ? C2 C1 N11 115.9(6) . . ? C2 C1 C6 121.9(2) . . ? N11 C1 C6 122.1(6) . . ? C2 C1 Cl1 124.2(3) . . ? N11 C1 Cl1 9.4(6) . . ? C6 C1 Cl1 113.9(3) . . ? C3 C2 C1 119.2(2) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.5(2) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C5 C4 C3 117.3(2) . . ? C5 C4 C7 119.6(2) . . ? C3 C4 C7 123.1(2) . . ? C4 C5 C6 122.6(2) . . ? C4 C5 H5A 118.7 . . ? C6 C5 H5A 118.7 . . ? C1 C6 C5 117.5(2) . . ? C1 C6 H6A 121.3 . . ? C5 C6 H6A 121.3 . . ? C17 C7 C4 126.7(3) . . ? C17 C7 H7A 116.6 . . ? C4 C7 H7A 116.7 . . ? N1 Cl11 O1 123(2) . . ? N1 Cl11 O2 65.5(16) . . ? O1 Cl11 O2 168.2(7) . . ? N1 Cl11 C11 24.3(15) . . ? O1 Cl11 C11 102.5(6) . . ? O2 Cl11 C11 87.4(3) . . ? Cl11 N1 O1 35.0(14) . . ? Cl11 N1 O2 89.8(16) . . ? O1 N1 O2 124.3(8) . . ? Cl11 N1 C11 146(2) . . ? O1 N1 C11 115.1(9) . . ? O2 N1 C11 119.8(9) . . ? Cl11 O1 N1 22.1(6) . . ? N1 O2 Cl11 24.7(4) . . ? C12 C11 N1 115.9(6) . . ? C12 C11 C16 121.9(2) . . ? N1 C11 C16 122.1(6) . . ? C12 C11 Cl11 124.2(3) . . ? N1 C11 Cl11 9.4(6) . . ? C16 C11 Cl11 113.9(3) . . ? C13 C12 C11 119.2(2) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 121.5(2) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C15 C14 C13 117.3(2) . . ? C15 C14 C17 119.6(2) . . ? C13 C14 C17 123.1(2) . . ? C14 C15 C16 122.6(2) . . ? C14 C15 H15A 118.7 . . ? C16 C15 H15A 118.7 . . ? C11 C16 C15 117.5(2) . . ? C11 C16 H16A 121.3 . . ? C15 C16 H16A 121.3 . . ? C7 C17 C14 126.7(3) . . ? C7 C17 H17A 116.6 . . ? C14 C17 H17A 116.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 Cl1 N11 O11 -170.5(12) . . . . ? C1 Cl1 N11 O11 37(5) . . . . ? O11 Cl1 N11 O12 170.5(12) . . . . ? C1 Cl1 N11 O12 -153(5) . . . . ? O11 Cl1 N11 C1 -37(5) . . . . ? O12 Cl1 N11 C1 153(5) . . . . ? O12 Cl1 O11 N11 133(6) . . . . ? C1 Cl1 O11 N11 -15(2) . . . . ? O12 N11 O11 Cl1 -11.5(15) . . . . ? C1 N11 O11 Cl1 159(3) . . . . ? O11 N11 O12 Cl1 6.6(9) . . . . ? C1 N11 O12 Cl1 -163(3) . . . . ? O11 Cl1 O12 N11 -137(5) . . . . ? C1 Cl1 O12 N11 10.8(19) . . . . ? Cl1 N11 C1 C2 -153(4) . . . . ? O11 N11 C1 C2 -175.0(9) . . . . ? O12 N11 C1 C2 -4.4(14) . . . . ? Cl1 N11 C1 C6 32(5) . . . . ? O11 N11 C1 C6 9.4(15) . . . . ? O12 N11 C1 C6 180.0(8) . . . . ? O11 N11 C1 Cl1 -22(4) . . . . ? O12 N11 C1 Cl1 148(5) . . . . ? N11 Cl1 C1 C2 30(5) . . . . ? O11 Cl1 C1 C2 179.0(7) . . . . ? O12 Cl1 C1 C2 5.3(5) . . . . ? O11 Cl1 C1 N11 149(5) . . . . ? O12 Cl1 C1 N11 -24(4) . . . . ? N11 Cl1 C1 C6 -151(4) . . . . ? O11 Cl1 C1 C6 -1.8(8) . . . . ? O12 Cl1 C1 C6 -175.4(3) . . . . ? N11 C1 C2 C3 -176.4(7) . . . . ? C6 C1 C2 C3 -0.8(4) . . . . ? Cl1 C1 C2 C3 178.4(3) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C2 C3 C4 C7 179.9(2) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C7 C4 C5 C6 180.0(2) . . . . ? C2 C1 C6 C5 0.6(4) . . . . ? N11 C1 C6 C5 176.0(7) . . . . ? Cl1 C1 C6 C5 -178.6(3) . . . . ? C4 C5 C6 C1 -0.5(4) . . . . ? C5 C4 C7 C17 175.7(3) . . . . ? C3 C4 C7 C17 -4.9(5) . . . . ? O2 Cl11 N1 O1 170.5(12) . . . . ? C11 Cl11 N1 O1 -37(5) . . . . ? O1 Cl11 N1 O2 -170.5(12) . . . . ? C11 Cl11 N1 O2 153(5) . . . . ? O1 Cl11 N1 C11 37(5) . . . . ? O2 Cl11 N1 C11 -153(5) . . . . ? O2 Cl11 O1 N1 -133(6) . . . . ? C11 Cl11 O1 N1 15(2) . . . . ? O2 N1 O1 Cl11 11.5(15) . . . . ? C11 N1 O1 Cl11 -159(3) . . . . ? O1 N1 O2 Cl11 -6.6(9) . . . . ? C11 N1 O2 Cl11 163(3) . . . . ? O1 Cl11 O2 N1 137(5) . . . . ? C11 Cl11 O2 N1 -10.8(19) . . . . ? Cl11 N1 C11 C12 153(4) . . . . ? O1 N1 C11 C12 175.0(9) . . . . ? O2 N1 C11 C12 4.4(14) . . . . ? Cl11 N1 C11 C16 -32(5) . . . . ? O1 N1 C11 C16 -9.4(15) . . . . ? O2 N1 C11 C16 -180.0(8) . . . . ? O1 N1 C11 Cl11 22(4) . . . . ? O2 N1 C11 Cl11 -148(5) . . . . ? N1 Cl11 C11 C12 -30(5) . . . . ? O1 Cl11 C11 C12 -179.0(7) . . . . ? O2 Cl11 C11 C12 -5.3(5) . . . . ? O1 Cl11 C11 N1 -149(5) . . . . ? O2 Cl11 C11 N1 24(4) . . . . ? N1 Cl11 C11 C16 151(4) . . . . ? O1 Cl11 C11 C16 1.8(8) . . . . ? O2 Cl11 C11 C16 175.4(3) . . . . ? N1 C11 C12 C13 176.4(7) . . . . ? C16 C11 C12 C13 0.8(4) . . . . ? Cl11 C11 C12 C13 -178.4(3) . . . . ? C11 C12 C13 C14 -0.8(4) . . . . ? C12 C13 C14 C15 0.7(4) . . . . ? C12 C13 C14 C17 -179.9(2) . . . . ? C13 C14 C15 C16 -0.6(3) . . . . ? C17 C14 C15 C16 -180.0(2) . . . . ? C12 C11 C16 C15 -0.6(4) . . . . ? N1 C11 C16 C15 -176.0(7) . . . . ? Cl11 C11 C16 C15 178.6(3) . . . . ? C14 C15 C16 C11 0.5(4) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.7(3) . . . . ? C13 C14 C17 C7 4.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 27.78 _diffrn_measured_fraction_theta_full 0.910 _refine_diff_density_max 0.139 _refine_diff_density_min -0.100 _refine_diff_density_rms 0.031 # start Validation Reply Form _vrf_ABSTM02_CNS-ClBzI-small-P21 ; PROBLEM: The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; _vrf_SYMMG02_CNS-ClBzI-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-ClBzI-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.91 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; _vrf_PLAT061_CNS-ClBzI-small-P21 ; PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.49 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; # end Validation Reply Form #===END data_CNS-ClBzII-small-P21_c _database_code_depnum_ccdc_archive 'CCDC 761202' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.91412(16) _cell_length_b 12.9559(6) _cell_length_c 12.2307(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.221(4) _cell_angle_gamma 90.00 _cell_volume 619.25(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5714 _cell_measurement_theta_min 4.5779 _cell_measurement_theta_max 31.8554 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.794703 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7100 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator synchrotron _diffrn_measurement_device_type 'Kuma 6-circle' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean 8.2896 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8061 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 26.39 _reflns_number_total 2283 _reflns_number_gt 1651 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0947P)^2^+0.0214P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(18) _refine_ls_number_reflns 2283 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1741 _refine_ls_wR_factor_gt 0.1580 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3699(10) -0.4604(2) -0.1762(4) 0.1167(6) Uani 0.50 1 d P . . N11 N 0.363(2) -0.4151(6) -0.1713(7) 0.0875(10) Uani 0.50 1 d P . . O11 O 0.316(2) -0.4980(5) -0.1233(6) 0.1336(13) Uani 0.50 1 d P . . O12 O 0.4998(13) -0.4127(4) -0.2583(4) 0.1192(7) Uani 0.50 1 d P . . C1 C 0.2617(7) -0.3297(2) -0.1229(2) 0.0800(4) Uani 1 1 d . . . C2 C 0.3156(6) -0.2393(2) -0.1793(2) 0.0845(4) Uani 1 1 d . . . H2A H 0.4131 -0.2407 -0.2469 0.101 Uiso 1 1 calc R . . C3 C 0.2229(3) -0.14765(10) -0.13393(10) 0.0814(4) Uani 1 1 d . . . H3A H 0.2577 -0.0866 -0.1717 0.098 Uiso 1 1 calc R . . C4 C 0.0781(3) -0.14357(8) -0.03291(9) 0.0712(3) Uani 1 1 d . . . C5 C 0.0279(3) -0.23638(9) 0.02097(9) 0.0774(4) Uani 1 1 d . . . H5A H -0.0704 -0.2355 0.0884 0.093 Uiso 1 1 calc R . . C6 C 0.1196(3) -0.32943(10) -0.02268(10) 0.0819(4) Uani 1 1 d . . . H6A H 0.0862 -0.3908 0.0147 0.098 Uiso 1 1 calc R . . C7 C -0.0243(3) -0.04691(6) 0.01865(9) 0.0759(4) Uani 1 1 d . . . H7 H -0.1340 -0.0525 0.0839 0.091 Uiso 1 1 calc R . . Cl11 Cl -0.3702(3) 0.46058(6) 0.17619(9) 0.1167(6) Uani 0.50 1 d PR . . N1 N -0.3624(3) 0.41564(6) 0.17092(9) 0.0875(10) Uani 0.50 1 d PR . . O1 O -0.3155(3) 0.49801(6) 0.12301(9) 0.1336(13) Uani 0.50 1 d PR . . O2 O -0.4987(3) 0.41305(6) 0.25823(9) 0.1192(7) Uani 0.50 1 d PR . . C11 C -0.2616(3) 0.32979(6) 0.12277(9) 0.0800(4) Uani 1 1 d R . . C12 C -0.3157(3) 0.23920(6) 0.17937(9) 0.0845(4) Uani 1 1 d R . . H12A H -0.4132 0.2406 0.2470 0.101 Uiso 1 1 calc R . . C13 C -0.2229(3) 0.14765(10) 0.13393(10) 0.0814(4) Uani 1 1 d . . . H13A H -0.2577 0.0865 0.1716 0.098 Uiso 1 1 calc R . . C14 C -0.0781(3) 0.14357(8) 0.03291(9) 0.0712(3) Uani 1 1 d . . . C15 C -0.0279(3) 0.23638(9) -0.02097(9) 0.0774(4) Uani 1 1 d . . . H15A H 0.0704 0.2355 -0.0884 0.093 Uiso 1 1 calc R . . C16 C -0.1196(3) 0.32943(10) 0.02268(10) 0.0819(4) Uani 1 1 d . . . H16A H -0.0862 0.3908 -0.0148 0.098 Uiso 1 1 calc R . . C17 C 0.0243(3) 0.04691(6) -0.01865(9) 0.0759(4) Uani 1 1 d . . . H17 H 0.1340 0.0525 -0.0839 0.091 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1174(8) 0.0960(12) 0.1364(12) -0.0455(11) 0.0038(7) 0.0235(9) N11 0.0879(16) 0.072(2) 0.102(2) -0.0080(18) 0.0007(14) 0.0067(18) O11 0.174(3) 0.0802(18) 0.150(3) 0.0106(15) 0.039(2) 0.0145(15) O12 0.1609(19) 0.0968(16) 0.1031(13) -0.0237(12) 0.0371(14) 0.0182(12) C1 0.0667(6) 0.0928(9) 0.0803(8) -0.0145(6) 0.0018(5) 0.0054(5) C2 0.0757(7) 0.1078(10) 0.0710(7) -0.0041(6) 0.0118(6) -0.0010(6) C3 0.0780(7) 0.0883(9) 0.0786(7) 0.0066(6) 0.0089(6) -0.0044(5) C4 0.0600(6) 0.0818(8) 0.0717(6) -0.0020(5) 0.0039(5) -0.0019(5) C5 0.0743(7) 0.0878(9) 0.0709(7) 0.0020(5) 0.0101(5) 0.0009(5) C6 0.0811(7) 0.0788(8) 0.0859(8) 0.0022(5) 0.0051(6) 0.0014(5) C7 0.0688(6) 0.0861(9) 0.0732(7) 0.0021(5) 0.0075(5) -0.0029(5) Cl11 0.1174(8) 0.0960(12) 0.1364(12) -0.0455(11) 0.0038(7) 0.0235(9) N1 0.0879(16) 0.072(2) 0.102(2) -0.0080(18) 0.0007(14) 0.0067(18) O1 0.174(3) 0.0802(18) 0.150(3) 0.0106(15) 0.039(2) 0.0145(15) O2 0.1609(19) 0.0968(16) 0.1031(13) -0.0237(12) 0.0371(14) 0.0182(12) C11 0.0667(6) 0.0928(9) 0.0803(8) -0.0145(6) 0.0018(5) 0.0054(5) C12 0.0757(7) 0.1078(10) 0.0710(7) -0.0041(6) 0.0118(6) -0.0010(6) C13 0.0780(7) 0.0883(9) 0.0786(7) 0.0066(6) 0.0089(6) -0.0044(5) C14 0.0600(6) 0.0818(8) 0.0717(6) -0.0020(5) 0.0039(5) -0.0019(5) C15 0.0743(7) 0.0878(9) 0.0709(7) 0.0020(5) 0.0101(5) 0.0009(5) C16 0.0811(7) 0.0788(8) 0.0859(8) 0.0022(5) 0.0051(6) 0.0014(5) C17 0.0688(6) 0.0861(9) 0.0732(7) 0.0021(5) 0.0075(5) -0.0029(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.590(6) . ? Cl1 O11 0.846(5) . ? Cl1 O12 1.306(6) . ? Cl1 C1 1.872(3) . ? N11 O12 1.217(10) . ? N11 O11 1.243(11) . ? N11 C1 1.327(7) . ? C1 C6 1.374(3) . ? C1 C2 1.382(4) . ? C2 C3 1.368(3) . ? C2 H2A 0.9300 . ? C3 C4 1.3890(17) . ? C3 H3A 0.9300 . ? C4 C5 1.3904(16) . ? C4 C7 1.4681(15) . ? C5 C6 1.3743(16) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.3158(16) . ? C7 H7 0.9300 . ? Cl11 N1 0.5868 . ? Cl11 O1 0.8484 . ? Cl11 O2 1.3022 . ? Cl11 C11 1.8735 . ? N1 O2 1.2207 . ? N1 O1 1.2362 . ? N1 C11 1.3288 . ? C11 C16 1.3726(16) . ? C11 C12 1.3850 . ? C12 C13 1.3676(15) . ? C12 H12A 0.9300 . ? C13 C14 1.3890(17) . ? C13 H13A 0.9300 . ? C14 C15 1.3904(16) . ? C14 C17 1.4681(15) . ? C15 C16 1.3743(16) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 118.8(16) . . ? N11 Cl1 O12 68.2(12) . . ? O11 Cl1 O12 170.0(7) . . ? N11 Cl1 C1 18.9(11) . . ? O11 Cl1 C1 100.6(7) . . ? O12 Cl1 C1 86.9(3) . . ? Cl1 N11 O12 85.1(12) . . ? Cl1 N11 O11 36.6(11) . . ? O12 N11 O11 121.3(7) . . ? Cl1 N11 C1 152.8(16) . . ? O12 N11 C1 121.8(7) . . ? O11 N11 C1 116.9(7) . . ? Cl1 O11 N11 24.6(5) . . ? N11 O12 Cl1 26.8(3) . . ? N11 C1 C6 123.1(4) . . ? N11 C1 C2 115.2(4) . . ? C6 C1 C2 121.6(2) . . ? N11 C1 Cl1 8.3(5) . . ? C6 C1 Cl1 115.1(2) . . ? C2 C1 Cl1 123.3(2) . . ? C3 C2 C1 118.8(2) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C2 C3 C4 121.65(15) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 117.66(11) . . ? C3 C4 C7 123.33(10) . . ? C5 C4 C7 119.01(10) . . ? C6 C5 C4 121.85(11) . . ? C6 C5 H5A 119.1 . . ? C4 C5 H5A 119.1 . . ? C5 C6 C1 118.42(15) . . ? C5 C6 H6A 120.8 . . ? C1 C6 H6A 120.8 . . ? C17 C7 C4 126.21(13) . . ? C17 C7 H7 116.9 . . ? C4 C7 H7 116.9 . . ? N1 Cl11 O1 117.8 . . ? N1 Cl11 O2 68.9 . . ? O1 Cl11 O2 170.5 . . ? N1 Cl11 C11 18.2 . . ? O1 Cl11 C11 100.2 . . ? O2 Cl11 C11 86.9 . . ? Cl11 N1 O2 84.4 . . ? Cl11 N1 O1 37.4 . . ? O2 N1 O1 121.5 . . ? Cl11 N1 C11 153.9 . . ? O2 N1 C11 121.3 . . ? O1 N1 C11 117.2 . . ? Cl11 O1 N1 24.8 . . ? N1 O2 Cl11 26.6 . . ? N1 C11 C16 122.91(5) . . ? N1 C11 C12 115.5 . . ? C16 C11 C12 121.59(5) . . ? N1 C11 Cl11 7.9 . . ? C16 C11 Cl11 115.17(5) . . ? C12 C11 Cl11 123.2 . . ? C13 C12 C11 118.71(7) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? C12 C13 C14 121.70(11) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C13 C14 C15 117.66(11) . . ? C13 C14 C17 123.33(10) . . ? C15 C14 C17 119.01(10) . . ? C16 C15 C14 121.85(11) . . ? C16 C15 H15A 119.1 . . ? C14 C15 H15A 119.1 . . ? C15 C16 C11 118.49(10) . . ? C15 C16 H16A 120.8 . . ? C11 C16 H16A 120.8 . . ? C7 C17 C14 126.21(13) . . ? C7 C17 H17 116.9 . . ? C14 C17 H17 116.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.0(9) . . . . ? C1 Cl1 N11 O12 -171(3) . . . . ? O12 Cl1 N11 O11 -172.0(9) . . . . ? C1 Cl1 N11 O11 17(4) . . . . ? O11 Cl1 N11 C1 -17(4) . . . . ? O12 Cl1 N11 C1 171(3) . . . . ? O12 Cl1 O11 N11 132(5) . . . . ? C1 Cl1 O11 N11 -5.5(12) . . . . ? O12 N11 O11 Cl1 -9.3(10) . . . . ? C1 N11 O11 Cl1 171.5(19) . . . . ? O11 N11 O12 Cl1 5.6(6) . . . . ? C1 N11 O12 Cl1 -175.3(17) . . . . ? O11 Cl1 O12 N11 -136(4) . . . . ? C1 Cl1 O12 N11 2.8(10) . . . . ? Cl1 N11 C1 C6 13(3) . . . . ? O12 N11 C1 C6 -177.3(5) . . . . ? O11 N11 C1 C6 1.9(10) . . . . ? Cl1 N11 C1 C2 -168(3) . . . . ? O12 N11 C1 C2 1.4(9) . . . . ? O11 N11 C1 C2 -179.5(7) . . . . ? O12 N11 C1 Cl1 170(4) . . . . ? O11 N11 C1 Cl1 -11(2) . . . . ? O11 Cl1 C1 N11 165(3) . . . . ? O12 Cl1 C1 N11 -8(3) . . . . ? N11 Cl1 C1 C6 -168(3) . . . . ? O11 Cl1 C1 C6 -2.9(7) . . . . ? O12 Cl1 C1 C6 -176.1(3) . . . . ? N11 Cl1 C1 C2 13(3) . . . . ? O11 Cl1 C1 C2 177.8(6) . . . . ? O12 Cl1 C1 C2 4.5(4) . . . . ? N11 C1 C2 C3 -179.0(4) . . . . ? C6 C1 C2 C3 -0.3(3) . . . . ? Cl1 C1 C2 C3 179.0(2) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 -0.3(2) . . . . ? C2 C3 C4 C7 179.90(16) . . . . ? C3 C4 C5 C6 0.52(18) . . . . ? C7 C4 C5 C6 -179.72(10) . . . . ? C4 C5 C6 C1 -0.6(2) . . . . ? N11 C1 C6 C5 179.0(4) . . . . ? C2 C1 C6 C5 0.5(3) . . . . ? Cl1 C1 C6 C5 -178.92(16) . . . . ? C3 C4 C7 C17 -4.5(2) . . . . ? C5 C4 C7 C17 175.76(13) . . . . ? O1 Cl11 N1 O2 -172.5 . . . . ? C11 Cl11 N1 O2 171.1 . . . . ? O2 Cl11 N1 O1 172.5 . . . . ? C11 Cl11 N1 O1 -16.4 . . . . ? O1 Cl11 N1 C11 16.4 . . . . ? O2 Cl11 N1 C11 -171.1 . . . . ? O2 Cl11 O1 N1 -132.9 . . . . ? C11 Cl11 O1 N1 5.1 . . . . ? O2 N1 O1 Cl11 8.7 . . . . ? C11 N1 O1 Cl11 -172.0 . . . . ? O1 N1 O2 Cl11 -5.3 . . . . ? C11 N1 O2 Cl11 175.4 . . . . ? O1 Cl11 O2 N1 136.0 . . . . ? C11 Cl11 O2 N1 -2.8 . . . . ? Cl11 N1 C11 C16 -12.97(8) . . . . ? O2 N1 C11 C16 177.42(8) . . . . ? O1 N1 C11 C16 -1.86(8) . . . . ? Cl11 N1 C11 C12 168.3 . . . . ? O2 N1 C11 C12 -1.3 . . . . ? O1 N1 C11 C12 179.5 . . . . ? O2 N1 C11 Cl11 -169.6 . . . . ? O1 N1 C11 Cl11 11.1 . . . . ? O1 Cl11 C11 N1 -165.3 . . . . ? O2 Cl11 C11 N1 8.3 . . . . ? N1 Cl11 C11 C16 167.99(8) . . . . ? O1 Cl11 C11 C16 2.68(8) . . . . ? O2 Cl11 C11 C16 176.30(8) . . . . ? N1 Cl11 C11 C12 -12.6 . . . . ? O1 Cl11 C11 C12 -177.9 . . . . ? O2 Cl11 C11 C12 -4.3 . . . . ? N1 C11 C12 C13 179.03(8) . . . . ? C16 C11 C12 C13 0.33(9) . . . . ? Cl11 C11 C12 C13 -179.06(8) . . . . ? C11 C12 C13 C14 -0.26(14) . . . . ? C12 C13 C14 C15 0.35(18) . . . . ? C12 C13 C14 C17 -179.89(8) . . . . ? C13 C14 C15 C16 -0.52(18) . . . . ? C17 C14 C15 C16 179.72(10) . . . . ? C14 C15 C16 C11 0.58(18) . . . . ? N1 C11 C16 C15 -179.09(8) . . . . ? C12 C11 C16 C15 -0.49(14) . . . . ? Cl11 C11 C16 C15 178.95(8) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 4.5(2) . . . . ? C15 C14 C17 C7 -175.76(13) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.158 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.035 # start Validation Reply Form _vrf_SYMMG02_CNS-ClBzII-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; # end Validation Reply Form #===END data_CNS-ClBzII-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761203' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.91412(16) _cell_length_b 12.9559(6) _cell_length_c 12.2307(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.221(4) _cell_angle_gamma 90.00 _cell_volume 619.25(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5714 _cell_measurement_theta_min 4.5779 _cell_measurement_theta_max 31.8554 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.794703 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7100 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator synchrotron _diffrn_measurement_device_type 'Kuma 6-circle' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean 8.2896 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8061 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 26.39 _reflns_number_total 2283 _reflns_number_gt 1651 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0947P)^2^+0.0214P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(3) _refine_ls_number_reflns 2283 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1723 _refine_ls_wR_factor_gt 0.1559 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3694(9) -0.4606(2) -0.1761(3) 0.1170(6) Uani 0.483(2) 1 d P . . N11 N 0.363(2) -0.4156(5) -0.1709(6) 0.0872(9) Uani 0.517(2) 1 d P . . O11 O 0.3143(17) -0.4974(4) -0.1227(5) 0.1341(13) Uani 0.517(2) 1 d P . . O12 O 0.4985(12) -0.4129(3) -0.2579(3) 0.1189(7) Uani 0.517(2) 1 d P . . C1 C 0.2610(6) -0.3297(2) -0.1227(2) 0.0800(4) Uani 1 1 d . . . C2 C 0.3151(6) -0.2390(2) -0.17931(18) 0.0845(4) Uani 1 1 d . . . H2A H 0.4125 -0.2404 -0.2469 0.101 Uiso 1 1 calc R . . C3 C 0.2228(3) -0.14764(10) -0.13394(10) 0.0814(4) Uani 1 1 d . . . H3A H 0.2577 -0.0865 -0.1716 0.098 Uiso 1 1 calc R . . C4 C 0.0781(3) -0.14357(8) -0.03294(9) 0.0711(3) Uani 1 1 d . . . C5 C 0.0278(3) -0.23639(9) 0.02099(9) 0.0774(4) Uani 1 1 d . . . H5A H -0.0706 -0.2355 0.0884 0.093 Uiso 1 1 calc R . . C6 C 0.1196(3) -0.32943(10) -0.02266(10) 0.0818(4) Uani 1 1 d . . . H6A H 0.0866 -0.3908 0.0148 0.098 Uiso 1 1 calc R . . C7 C -0.0247(2) -0.04691(6) 0.01871(8) 0.0759(4) Uani 1 1 d . . . H7 H -0.1347 -0.0525 0.0839 0.091 Uiso 1 1 calc R . . Cl11 Cl -0.3706(2) 0.46057(6) 0.17625(8) 0.1170(6) Uani 0.517(2) 1 d PR . . N1 N -0.3627(2) 0.41563(6) 0.17098(8) 0.0872(9) Uani 0.483(2) 1 d PR . . O1 O -0.3158(2) 0.49801(6) 0.12308(8) 0.1341(13) Uani 0.483(2) 1 d PR . . O2 O -0.4990(2) 0.41304(6) 0.25830(8) 0.1189(7) Uani 0.483(2) 1 d PR . . C11 C -0.2619(2) 0.32979(6) 0.12284(8) 0.0800(4) Uani 1 1 d R . . C12 C -0.3160(2) 0.23919(6) 0.17943(8) 0.0845(4) Uani 1 1 d R . . H12A H -0.4138 0.2406 0.2470 0.101 Uiso 1 1 calc R . . C13 C -0.2228(3) 0.14764(10) 0.13394(10) 0.0814(4) Uani 1 1 d . . . H13A H -0.2573 0.0865 0.1717 0.098 Uiso 1 1 calc R . . C14 C -0.0781(3) 0.14357(8) 0.03294(9) 0.0711(3) Uani 1 1 d . . . C15 C -0.0278(3) 0.23639(9) -0.02099(9) 0.0774(4) Uani 1 1 d . . . H15A H 0.0706 0.2355 -0.0884 0.093 Uiso 1 1 calc R . . C16 C -0.1196(3) 0.32943(10) 0.02266(10) 0.0818(4) Uani 1 1 d . . . H16A H -0.0861 0.3908 -0.0148 0.098 Uiso 1 1 calc R . . C17 C 0.0247(2) 0.04691(6) -0.01871(8) 0.0759(4) Uani 1 1 d . . . H17 H 0.1347 0.0525 -0.0839 0.091 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1172(7) 0.0971(11) 0.1364(11) -0.0464(10) 0.0041(7) 0.0234(9) N11 0.0872(16) 0.074(2) 0.100(2) -0.0082(17) 0.0006(14) 0.0061(17) O11 0.175(3) 0.0821(17) 0.149(3) 0.0106(15) 0.0398(19) 0.0148(15) O12 0.1608(19) 0.0966(15) 0.1028(13) -0.0236(12) 0.0372(14) 0.0185(12) C1 0.0666(6) 0.0928(9) 0.0803(7) -0.0145(6) 0.0018(5) 0.0055(5) C2 0.0756(7) 0.1077(10) 0.0710(7) -0.0041(6) 0.0117(6) -0.0010(6) C3 0.0779(7) 0.0880(8) 0.0787(7) 0.0065(5) 0.0087(6) -0.0043(5) C4 0.0599(5) 0.0818(8) 0.0716(6) -0.0020(5) 0.0039(5) -0.0019(5) C5 0.0742(7) 0.0877(8) 0.0710(7) 0.0021(5) 0.0100(5) 0.0011(5) C6 0.0811(7) 0.0786(8) 0.0858(8) 0.0021(5) 0.0052(6) 0.0015(5) C7 0.0687(6) 0.0862(8) 0.0731(7) 0.0020(5) 0.0075(5) -0.0029(5) Cl11 0.1172(7) 0.0971(11) 0.1364(11) -0.0464(10) 0.0041(7) 0.0234(9) N1 0.0872(16) 0.074(2) 0.100(2) -0.0082(17) 0.0006(14) 0.0061(17) O1 0.175(3) 0.0821(17) 0.149(3) 0.0106(15) 0.0398(19) 0.0148(15) O2 0.1608(19) 0.0966(15) 0.1028(13) -0.0236(12) 0.0372(14) 0.0185(12) C11 0.0666(6) 0.0928(9) 0.0803(7) -0.0145(6) 0.0018(5) 0.0055(5) C12 0.0756(7) 0.1077(10) 0.0710(7) -0.0041(6) 0.0117(6) -0.0010(6) C13 0.0779(7) 0.0880(8) 0.0787(7) 0.0065(5) 0.0087(6) -0.0043(5) C14 0.0599(5) 0.0818(8) 0.0716(6) -0.0020(5) 0.0039(5) -0.0019(5) C15 0.0742(7) 0.0877(8) 0.0710(7) 0.0021(5) 0.0100(5) 0.0011(5) C16 0.0811(7) 0.0786(8) 0.0858(8) 0.0021(5) 0.0052(6) 0.0015(5) C17 0.0687(6) 0.0862(8) 0.0731(7) 0.0020(5) 0.0075(5) -0.0029(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.587(6) . ? Cl1 O11 0.847(5) . ? Cl1 O12 1.302(6) . ? Cl1 C1 1.875(3) . ? N11 O12 1.215(9) . ? N11 O11 1.233(10) . ? N11 C1 1.332(7) . ? C1 C6 1.371(3) . ? C1 C2 1.385(3) . ? C2 C3 1.365(3) . ? C2 H2A 0.9300 . ? C3 C4 1.3886(17) . ? C3 H3A 0.9300 . ? C4 C5 1.3908(16) . ? C4 C7 1.4689(15) . ? C5 C6 1.3743(16) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.3169(15) . ? C7 H7 0.9300 . ? Cl11 N1 0.5868 . ? Cl11 O1 0.8484 . ? Cl11 O2 1.3022 . ? Cl11 C11 1.8735 . ? N1 O2 1.2207 . ? N1 O1 1.2362 . ? N1 C11 1.3287 . ? C11 C16 1.3741(15) . ? C11 C12 1.3850 . ? C12 C13 1.3685(14) . ? C12 H12A 0.9300 . ? C13 C14 1.3886(17) . ? C13 H13A 0.9300 . ? C14 C15 1.3908(16) . ? C14 C17 1.4689(15) . ? C15 C16 1.3743(16) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 117.4(14) . . ? N11 Cl1 O12 68.4(11) . . ? O11 Cl1 O12 170.9(6) . . ? N11 Cl1 C1 18.6(10) . . ? O11 Cl1 C1 99.6(5) . . ? O12 Cl1 C1 86.7(3) . . ? Cl1 N11 O12 84.9(11) . . ? Cl1 N11 O11 37.6(10) . . ? O12 N11 O11 122.1(6) . . ? Cl1 N11 C1 153.3(15) . . ? O12 N11 C1 121.3(6) . . ? O11 N11 C1 116.6(6) . . ? Cl1 O11 N11 25.0(4) . . ? N11 O12 Cl1 26.7(3) . . ? N11 C1 C6 122.9(4) . . ? N11 C1 C2 115.4(4) . . ? C6 C1 C2 121.6(2) . . ? N11 C1 Cl1 8.1(4) . . ? C6 C1 Cl1 115.1(2) . . ? C2 C1 Cl1 123.3(2) . . ? C3 C2 C1 118.75(18) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C2 C3 C4 121.67(14) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 117.69(10) . . ? C3 C4 C7 123.38(10) . . ? C5 C4 C7 118.93(10) . . ? C6 C5 C4 121.82(11) . . ? C6 C5 H5A 119.1 . . ? C4 C5 H5A 119.1 . . ? C5 C6 C1 118.43(15) . . ? C5 C6 H6A 120.8 . . ? C1 C6 H6A 120.8 . . ? C17 C7 C4 126.04(11) . . ? C17 C7 H7 117.0 . . ? C4 C7 H7 117.0 . . ? N1 Cl11 O1 117.8 . . ? N1 Cl11 O2 68.9 . . ? O1 Cl11 O2 170.5 . . ? N1 Cl11 C11 18.2 . . ? O1 Cl11 C11 100.2 . . ? O2 Cl11 C11 86.9 . . ? Cl11 N1 O2 84.4 . . ? Cl11 N1 O1 37.4 . . ? O2 N1 O1 121.5 . . ? Cl11 N1 C11 153.9 . . ? O2 N1 C11 121.3 . . ? O1 N1 C11 117.2 . . ? Cl11 O1 N1 24.8 . . ? N1 O2 Cl11 26.6 . . ? N1 C11 C16 122.91(5) . . ? N1 C11 C12 115.5 . . ? C16 C11 C12 121.59(5) . . ? N1 C11 Cl11 7.9 . . ? C16 C11 Cl11 115.17(5) . . ? C12 C11 Cl11 123.2 . . ? C13 C12 C11 118.66(6) . . ? C13 C12 H12A 120.7 . . ? C11 C12 H12A 120.7 . . ? C12 C13 C14 121.74(11) . . ? C12 C13 H13A 119.1 . . ? C14 C13 H13A 119.1 . . ? C13 C14 C15 117.69(10) . . ? C13 C14 C17 123.38(10) . . ? C15 C14 C17 118.93(10) . . ? C16 C15 C14 121.82(11) . . ? C16 C15 H15A 119.1 . . ? C14 C15 H15A 119.1 . . ? C15 C16 C11 118.50(10) . . ? C15 C16 H16A 120.7 . . ? C11 C16 H16A 120.7 . . ? C7 C17 C14 126.04(11) . . ? C7 C17 H17 117.0 . . ? C14 C17 H17 117.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.3(8) . . . . ? C1 Cl1 N11 O12 -170(3) . . . . ? O12 Cl1 N11 O11 -172.3(8) . . . . ? C1 Cl1 N11 O11 18(4) . . . . ? O11 Cl1 N11 C1 -18(4) . . . . ? O12 Cl1 N11 C1 170(3) . . . . ? O12 Cl1 O11 N11 128(5) . . . . ? C1 Cl1 O11 N11 -5.7(11) . . . . ? O12 N11 O11 Cl1 -9.1(10) . . . . ? C1 N11 O11 Cl1 171.1(18) . . . . ? O11 N11 O12 Cl1 5.6(6) . . . . ? C1 N11 O12 Cl1 -174.6(16) . . . . ? O11 Cl1 O12 N11 -131(4) . . . . ? C1 Cl1 O12 N11 3.3(10) . . . . ? Cl1 N11 C1 C6 15(3) . . . . ? O12 N11 C1 C6 -177.4(5) . . . . ? O11 N11 C1 C6 2.4(9) . . . . ? Cl1 N11 C1 C2 -167(3) . . . . ? O12 N11 C1 C2 1.0(8) . . . . ? O11 N11 C1 C2 -179.2(6) . . . . ? O12 N11 C1 Cl1 168(4) . . . . ? O11 N11 C1 Cl1 -12(2) . . . . ? O11 Cl1 C1 N11 164(3) . . . . ? O12 Cl1 C1 N11 -10(3) . . . . ? N11 Cl1 C1 C6 -167(3) . . . . ? O11 Cl1 C1 C6 -2.7(6) . . . . ? O12 Cl1 C1 C6 -176.1(3) . . . . ? N11 Cl1 C1 C2 14(3) . . . . ? O11 Cl1 C1 C2 177.9(5) . . . . ? O12 Cl1 C1 C2 4.5(4) . . . . ? N11 C1 C2 C3 -178.8(4) . . . . ? C6 C1 C2 C3 -0.4(3) . . . . ? Cl1 C1 C2 C3 179.08(19) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 -0.3(2) . . . . ? C2 C3 C4 C7 179.99(14) . . . . ? C3 C4 C5 C6 0.55(18) . . . . ? C7 C4 C5 C6 -179.73(10) . . . . ? C4 C5 C6 C1 -0.7(2) . . . . ? N11 C1 C6 C5 178.9(4) . . . . ? C2 C1 C6 C5 0.6(3) . . . . ? Cl1 C1 C6 C5 -178.90(15) . . . . ? C3 C4 C7 C17 -4.61(19) . . . . ? C5 C4 C7 C17 175.69(11) . . . . ? O1 Cl11 N1 O2 -172.5 . . . . ? C11 Cl11 N1 O2 171.1 . . . . ? O2 Cl11 N1 O1 172.5 . . . . ? C11 Cl11 N1 O1 -16.4 . . . . ? O1 Cl11 N1 C11 16.4 . . . . ? O2 Cl11 N1 C11 -171.1 . . . . ? O2 Cl11 O1 N1 -132.9 . . . . ? C11 Cl11 O1 N1 5.1 . . . . ? O2 N1 O1 Cl11 8.7 . . . . ? C11 N1 O1 Cl11 -172.0 . . . . ? O1 N1 O2 Cl11 -5.3 . . . . ? C11 N1 O2 Cl11 175.4 . . . . ? O1 Cl11 O2 N1 136.0 . . . . ? C11 Cl11 O2 N1 -2.8 . . . . ? Cl11 N1 C11 C16 -12.93(8) . . . . ? O2 N1 C11 C16 177.46(8) . . . . ? O1 N1 C11 C16 -1.83(8) . . . . ? Cl11 N1 C11 C12 168.3 . . . . ? O2 N1 C11 C12 -1.3 . . . . ? O1 N1 C11 C12 179.5 . . . . ? O2 N1 C11 Cl11 -169.6 . . . . ? O1 N1 C11 Cl11 11.1 . . . . ? O1 Cl11 C11 N1 -165.3 . . . . ? O2 Cl11 C11 N1 8.3 . . . . ? N1 Cl11 C11 C16 168.02(7) . . . . ? O1 Cl11 C11 C16 2.71(7) . . . . ? O2 Cl11 C11 C16 176.33(7) . . . . ? N1 Cl11 C11 C12 -12.6 . . . . ? O1 Cl11 C11 C12 -177.9 . . . . ? O2 Cl11 C11 C12 -4.3 . . . . ? N1 C11 C12 C13 179.09(7) . . . . ? C16 C11 C12 C13 0.35(9) . . . . ? Cl11 C11 C12 C13 -179.00(7) . . . . ? C11 C12 C13 C14 -0.33(13) . . . . ? C12 C13 C14 C15 0.43(17) . . . . ? C12 C13 C14 C17 -179.87(8) . . . . ? C13 C14 C15 C16 -0.55(18) . . . . ? C17 C14 C15 C16 179.73(10) . . . . ? C14 C15 C16 C11 0.57(17) . . . . ? N1 C11 C16 C15 -179.11(7) . . . . ? C12 C11 C16 C15 -0.47(14) . . . . ? Cl11 C11 C16 C15 178.94(8) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 4.61(19) . . . . ? C15 C14 C17 C7 -175.69(11) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.166 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.036 # start Validation Reply Form _vrf_SYMMG02_CNS-ClBzII-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21 model was generated from a proper P21/c model. ; # end Validation Reply Form #===END data_CNS-ClBzIII-small-P21_c _database_code_depnum_ccdc_archive 'CCDC 761204' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9164(2) _cell_length_b 12.9581(6) _cell_length_c 12.2370(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.238(2) _cell_angle_gamma 90.00 _cell_volume 620.03(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3467 _cell_measurement_theta_min 3.144 _cell_measurement_theta_max 24.3905 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.571507 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3459 _diffrn_reflns_av_R_equivalents 0.0121 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.87 _reflns_number_total 2308 _reflns_number_gt 1403 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0145P)^2^+0.1786P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2308 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0983 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 1.184 _refine_ls_restrained_S_all 1.183 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3715(11) -0.46021(14) -0.1754(4) 0.1142(16) Uani 0.50 1 d P . . N11 N 0.361(3) -0.4162(5) -0.1727(9) 0.0827(19) Uani 0.50 1 d P . . O11 O 0.3129(17) -0.4975(5) -0.1234(4) 0.128(2) Uani 0.50 1 d P . . O12 O 0.5018(9) -0.4127(3) -0.2584(3) 0.1095(11) Uani 0.50 1 d P . . C1 C 0.2610(4) -0.32905(15) -0.12323(16) 0.0703(5) Uani 1 1 d . . . C2 C 0.3154(4) -0.23925(17) -0.17900(15) 0.0803(6) Uani 1 1 d . . . H2A H 0.4142 -0.2407 -0.2463 0.096 Uiso 1 1 calc R . . C3 C 0.2225(4) -0.14753(14) -0.13417(15) 0.0747(5) Uani 1 1 d . . . H3A H 0.2565 -0.0866 -0.1721 0.090 Uiso 1 1 calc R . . C4 C 0.0779(4) -0.14339(13) -0.03289(14) 0.0642(5) Uani 1 1 d . . . C5 C 0.0287(4) -0.23573(14) 0.02049(14) 0.0715(5) Uani 1 1 d . . . H5A H -0.0690 -0.2347 0.0880 0.086 Uiso 1 1 calc R . . C6 C 0.1196(4) -0.32943(14) -0.02299(15) 0.0757(5) Uani 1 1 d . . . H6A H 0.0862 -0.3908 0.0143 0.091 Uiso 1 1 calc R . . C7 C -0.0237(4) -0.04639(12) 0.01837(15) 0.0713(5) Uani 1 1 d . . . H7 H -0.1328 -0.0519 0.0837 0.086 Uiso 1 1 calc R . . Cl11 Cl -0.3715(11) 0.46021(14) 0.1754(4) 0.1142(16) Uani 0.50 1 d P . . N1 N -0.361(3) 0.4162(5) 0.1727(9) 0.0827(19) Uani 0.50 1 d P . . O1 O -0.3129(17) 0.4975(5) 0.1234(4) 0.128(2) Uani 0.50 1 d P . . O2 O -0.5018(9) 0.4127(3) 0.2584(3) 0.1095(11) Uani 0.50 1 d P . . C11 C -0.2610(4) 0.32905(15) 0.12323(16) 0.0703(5) Uani 1 1 d . . . C12 C -0.3154(4) 0.23925(17) 0.17900(15) 0.0803(6) Uani 1 1 d . . . H12A H -0.4142 0.2407 0.2463 0.096 Uiso 1 1 calc R . . C13 C -0.2225(4) 0.14753(14) 0.13417(15) 0.0747(5) Uani 1 1 d . . . H13A H -0.2565 0.0866 0.1721 0.090 Uiso 1 1 calc R . . C14 C -0.0779(4) 0.14339(13) 0.03289(14) 0.0642(5) Uani 1 1 d . . . C15 C -0.0287(4) 0.23573(14) -0.02049(14) 0.0715(5) Uani 1 1 d . . . H15A H 0.0690 0.2347 -0.0880 0.086 Uiso 1 1 calc R . . C16 C -0.1196(4) 0.32943(14) 0.02299(15) 0.0757(5) Uani 1 1 d . . . H16A H -0.0862 0.3908 -0.0143 0.091 Uiso 1 1 calc R . . C17 C 0.0237(4) 0.04639(12) -0.01837(15) 0.0713(5) Uani 1 1 d . . . H17 H 0.1328 0.0519 -0.0837 0.086 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1123(14) 0.095(3) 0.135(3) -0.049(3) 0.0028(16) 0.026(2) N11 0.077(3) 0.066(5) 0.104(6) -0.003(5) 0.000(3) 0.010(4) O11 0.170(4) 0.074(3) 0.144(5) 0.004(3) 0.040(3) 0.013(2) O12 0.147(3) 0.090(2) 0.095(2) -0.0284(19) 0.034(2) 0.0161(19) C1 0.0587(11) 0.0777(14) 0.0739(13) -0.0148(10) -0.0023(9) 0.0055(10) C2 0.0693(12) 0.1064(16) 0.0659(12) -0.0044(12) 0.0090(10) -0.0002(11) C3 0.0684(12) 0.0804(13) 0.0758(13) 0.0091(10) 0.0080(10) -0.0035(10) C4 0.0510(10) 0.0749(12) 0.0663(12) -0.0047(10) -0.0004(9) -0.0012(8) C5 0.0686(12) 0.0823(13) 0.0639(11) 0.0006(10) 0.0082(9) -0.0022(10) C6 0.0747(12) 0.0746(13) 0.0778(14) 0.0029(10) 0.0033(10) 0.0031(10) C7 0.0627(11) 0.0802(13) 0.0712(12) 0.0044(10) 0.0053(9) -0.0025(10) Cl11 0.1123(14) 0.095(3) 0.135(3) -0.049(3) 0.0028(16) 0.026(2) N1 0.077(3) 0.066(5) 0.104(6) -0.003(5) 0.000(3) 0.010(4) O1 0.170(4) 0.074(3) 0.144(5) 0.004(3) 0.040(3) 0.013(2) O2 0.147(3) 0.090(2) 0.095(2) -0.0284(19) 0.034(2) 0.0161(19) C11 0.0587(11) 0.0777(14) 0.0739(13) -0.0148(10) -0.0023(9) 0.0055(10) C12 0.0693(12) 0.1064(16) 0.0659(12) -0.0044(12) 0.0090(10) -0.0002(11) C13 0.0684(12) 0.0804(13) 0.0758(13) 0.0091(10) 0.0080(10) -0.0035(10) C14 0.0510(10) 0.0749(12) 0.0663(12) -0.0047(10) -0.0004(9) -0.0012(8) C15 0.0686(12) 0.0823(13) 0.0639(11) 0.0006(10) 0.0082(9) -0.0022(10) C16 0.0747(12) 0.0746(13) 0.0778(14) 0.0029(10) 0.0033(10) 0.0031(10) C17 0.0627(11) 0.0802(13) 0.0712(12) 0.0044(10) 0.0053(9) -0.0025(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.573(7) . ? Cl1 O11 0.841(5) . ? Cl1 O12 1.316(6) . ? Cl1 C1 1.875(3) . ? N11 O12 1.215(12) . ? N11 O11 1.234(14) . ? N11 C1 1.349(6) . ? C1 C2 1.372(2) . ? C1 C6 1.374(2) . ? C2 C3 1.367(2) . ? C2 H2A 0.9300 . ? C3 C4 1.392(2) . ? C3 H3A 0.9300 . ? C4 C5 1.382(2) . ? C4 C7 1.470(2) . ? C5 C6 1.380(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.301(3) . ? C7 H7 0.9300 . ? Cl11 N1 0.573(7) . ? Cl11 O1 0.841(5) . ? Cl11 O2 1.316(6) . ? Cl11 C11 1.875(3) . ? N1 O2 1.215(12) . ? N1 O1 1.234(14) . ? N1 C11 1.349(6) . ? C11 C12 1.372(2) . ? C11 C16 1.374(2) . ? C12 C13 1.367(2) . ? C12 H12A 0.9300 . ? C13 C14 1.392(2) . ? C13 H13A 0.9300 . ? C14 C15 1.382(2) . ? C14 C17 1.470(2) . ? C15 C16 1.380(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 120(2) . . ? N11 Cl1 O12 67.2(16) . . ? O11 Cl1 O12 170.9(7) . . ? N11 Cl1 C1 19.7(15) . . ? O11 Cl1 C1 100.7(7) . . ? O12 Cl1 C1 86.9(2) . . ? Cl1 N11 O12 87.0(15) . . ? Cl1 N11 O11 36.0(15) . . ? O12 N11 O11 122.9(6) . . ? Cl1 N11 C1 152(2) . . ? O12 N11 C1 120.9(8) . . ? O11 N11 C1 116.1(8) . . ? Cl1 O11 N11 23.6(7) . . ? N11 O12 Cl1 25.8(3) . . ? N11 C1 C2 115.5(5) . . ? N11 C1 C6 122.6(5) . . ? C2 C1 C6 121.94(19) . . ? N11 C1 Cl1 8.2(7) . . ? C2 C1 Cl1 123.7(2) . . ? C6 C1 Cl1 114.4(2) . . ? C3 C2 C1 119.04(18) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 121.44(18) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.52(17) . . ? C5 C4 C7 119.36(16) . . ? C3 C4 C7 123.12(18) . . ? C6 C5 C4 122.24(17) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C1 C6 C5 117.81(18) . . ? C1 C6 H6A 121.1 . . ? C5 C6 H6A 121.1 . . ? C17 C7 C4 126.6(2) . . ? C17 C7 H7 116.7 . . ? C4 C7 H7 116.7 . . ? N1 Cl11 O1 120(2) . . ? N1 Cl11 O2 67.2(16) . . ? O1 Cl11 O2 170.9(7) . . ? N1 Cl11 C11 19.7(15) . . ? O1 Cl11 C11 100.7(7) . . ? O2 Cl11 C11 86.9(2) . . ? Cl11 N1 O2 87.0(15) . . ? Cl11 N1 O1 36.0(15) . . ? O2 N1 O1 122.9(6) . . ? Cl11 N1 C11 152(2) . . ? O2 N1 C11 120.9(8) . . ? O1 N1 C11 116.1(8) . . ? Cl11 O1 N1 23.6(7) . . ? N1 O2 Cl11 25.8(3) . . ? N1 C11 C12 115.5(5) . . ? N1 C11 C16 122.6(5) . . ? C12 C11 C16 121.94(19) . . ? N1 C11 Cl11 8.2(7) . . ? C12 C11 Cl11 123.7(2) . . ? C16 C11 Cl11 114.4(2) . . ? C13 C12 C11 119.04(18) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C14 121.44(18) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 117.52(17) . . ? C15 C14 C17 119.36(16) . . ? C13 C14 C17 123.12(18) . . ? C16 C15 C14 122.24(17) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C11 C16 C15 117.81(18) . . ? C11 C16 H16A 121.1 . . ? C15 C16 H16A 121.1 . . ? C7 C17 C14 126.6(2) . . ? C7 C17 H17 116.7 . . ? C14 C17 H17 116.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 174.2(9) . . . . ? C1 Cl1 N11 O12 -178(4) . . . . ? O12 Cl1 N11 O11 -174.2(10) . . . . ? C1 Cl1 N11 O11 7(5) . . . . ? O11 Cl1 N11 C1 -7(5) . . . . ? O12 Cl1 N11 C1 178(4) . . . . ? O12 Cl1 O11 N11 144(6) . . . . ? C1 Cl1 O11 N11 -2.5(16) . . . . ? O12 N11 O11 Cl1 -6.9(11) . . . . ? C1 N11 O11 Cl1 176(2) . . . . ? O11 N11 O12 Cl1 4.1(7) . . . . ? C1 N11 O12 Cl1 -179(2) . . . . ? O11 Cl1 O12 N11 -146(5) . . . . ? C1 Cl1 O12 N11 0.5(13) . . . . ? Cl1 N11 C1 C2 -175(4) . . . . ? O12 N11 C1 C2 3.0(10) . . . . ? O11 N11 C1 C2 -180.0(7) . . . . ? Cl1 N11 C1 C6 6(4) . . . . ? O12 N11 C1 C6 -175.9(6) . . . . ? O11 N11 C1 C6 1.1(12) . . . . ? O12 N11 C1 Cl1 178(5) . . . . ? O11 N11 C1 Cl1 -5(3) . . . . ? O11 Cl1 C1 N11 173(4) . . . . ? O12 Cl1 C1 N11 -1(4) . . . . ? N11 Cl1 C1 C2 5(4) . . . . ? O11 Cl1 C1 C2 178.8(6) . . . . ? O12 Cl1 C1 C2 3.8(4) . . . . ? N11 Cl1 C1 C6 -175(4) . . . . ? O11 Cl1 C1 C6 -1.0(7) . . . . ? O12 Cl1 C1 C6 -176.0(2) . . . . ? N11 C1 C2 C3 -179.8(5) . . . . ? C6 C1 C2 C3 -0.8(3) . . . . ? Cl1 C1 C2 C3 179.4(2) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C2 C3 C4 C7 179.66(16) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? C7 C4 C5 C6 -179.77(16) . . . . ? N11 C1 C6 C5 179.6(5) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? Cl1 C1 C6 C5 -179.5(2) . . . . ? C4 C5 C6 C1 -0.5(3) . . . . ? C5 C4 C7 C17 175.8(2) . . . . ? C3 C4 C7 C17 -4.4(3) . . . . ? O1 Cl11 N1 O2 -174.2(9) . . . . ? C11 Cl11 N1 O2 178(4) . . . . ? O2 Cl11 N1 O1 174.2(10) . . . . ? C11 Cl11 N1 O1 -7(5) . . . . ? O1 Cl11 N1 C11 7(5) . . . . ? O2 Cl11 N1 C11 -178(4) . . . . ? O2 Cl11 O1 N1 -144(6) . . . . ? C11 Cl11 O1 N1 2.5(16) . . . . ? O2 N1 O1 Cl11 6.9(11) . . . . ? C11 N1 O1 Cl11 -176(2) . . . . ? O1 N1 O2 Cl11 -4.1(7) . . . . ? C11 N1 O2 Cl11 179(2) . . . . ? O1 Cl11 O2 N1 146(5) . . . . ? C11 Cl11 O2 N1 -0.5(13) . . . . ? Cl11 N1 C11 C12 175(4) . . . . ? O2 N1 C11 C12 -3.0(10) . . . . ? O1 N1 C11 C12 180.0(7) . . . . ? Cl11 N1 C11 C16 -6(4) . . . . ? O2 N1 C11 C16 175.9(6) . . . . ? O1 N1 C11 C16 -1.1(12) . . . . ? O2 N1 C11 Cl11 -178(5) . . . . ? O1 N1 C11 Cl11 5(3) . . . . ? O1 Cl11 C11 N1 -173(4) . . . . ? O2 Cl11 C11 N1 1(4) . . . . ? N1 Cl11 C11 C12 -5(4) . . . . ? O1 Cl11 C11 C12 -178.8(6) . . . . ? O2 Cl11 C11 C12 -3.8(4) . . . . ? N1 Cl11 C11 C16 175(4) . . . . ? O1 Cl11 C11 C16 1.0(7) . . . . ? O2 Cl11 C11 C16 176.0(2) . . . . ? N1 C11 C12 C13 179.8(5) . . . . ? C16 C11 C12 C13 0.8(3) . . . . ? Cl11 C11 C12 C13 -179.4(2) . . . . ? C11 C12 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C12 C13 C14 C17 -179.66(16) . . . . ? C13 C14 C15 C16 -0.4(2) . . . . ? C17 C14 C15 C16 179.77(16) . . . . ? N1 C11 C16 C15 -179.6(5) . . . . ? C12 C11 C16 C15 -0.7(3) . . . . ? Cl11 C11 C16 C15 179.49(19) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.8(2) . . . . ? C13 C14 C17 C7 4.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.863 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.863 _refine_diff_density_max 0.089 _refine_diff_density_min -0.098 _refine_diff_density_rms 0.022 # start Validation Reply Form _vrf_SYMMG02_CNS-ClBzIII-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-ClBzIII-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.86 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:23. ; # end Validation Reply Form #===END data_CNS-ClBzIII-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761205' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9164(2) _cell_length_b 12.9581(6) _cell_length_c 12.2370(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.238(2) _cell_angle_gamma 90.00 _cell_volume 620.03(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3467 _cell_measurement_theta_min 3.144 _cell_measurement_theta_max 24.3905 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.571507 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3459 _diffrn_reflns_av_R_equivalents 0.0121 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.87 _reflns_number_total 2308 _reflns_number_gt 1403 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0145P)^2^+0.1786P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(2) _refine_ls_number_reflns 2308 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0898 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.0903 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3702(8) -0.45988(12) -0.1752(3) 0.1112(11) Uani 0.408(2) 1 d P . . N11 N 0.365(2) -0.4149(4) -0.1735(7) 0.0889(16) Uani 0.592(2) 1 d P . . O11 O 0.3121(13) -0.4978(3) -0.1239(3) 0.1218(17) Uani 0.592(2) 1 d P . . O12 O 0.5021(7) -0.4132(2) -0.2585(2) 0.1090(9) Uani 0.592(2) 1 d P . . C1 C 0.2613(4) -0.32914(13) -0.12322(13) 0.0710(4) Uani 1 1 d . . . C2 C 0.3155(4) -0.23921(14) -0.17921(12) 0.0793(5) Uani 1 1 d . . . H2A H 0.4138 -0.2406 -0.2466 0.095 Uiso 1 1 calc R . . C3 C 0.2224(4) -0.14756(12) -0.13409(13) 0.0755(4) Uani 1 1 d . . . H3A H 0.2565 -0.0866 -0.1720 0.091 Uiso 1 1 calc R . . C4 C 0.0780(3) -0.14315(11) -0.03306(11) 0.0636(4) Uani 1 1 d . . . C5 C 0.0288(4) -0.23588(12) 0.02050(12) 0.0717(4) Uani 1 1 d . . . H5A H -0.0689 -0.2349 0.0880 0.086 Uiso 1 1 calc R . . C6 C 0.1199(4) -0.32925(12) -0.02300(13) 0.0758(4) Uani 1 1 d . . . H6A H 0.0866 -0.3906 0.0144 0.091 Uiso 1 1 calc R . . C7 C -0.0236(4) -0.04631(10) 0.01824(13) 0.0709(4) Uani 1 1 d . . . H7 H -0.1328 -0.0519 0.0835 0.085 Uiso 1 1 calc R . . Cl11 Cl -0.3702(8) 0.45988(12) 0.1752(3) 0.1112(11) Uani 0.592(2) 1 d P . . N1 N -0.365(2) 0.4149(4) 0.1735(7) 0.0889(16) Uani 0.408(2) 1 d P . . O1 O -0.3121(13) 0.4978(3) 0.1239(3) 0.1218(17) Uani 0.408(2) 1 d P . . O2 O -0.5021(7) 0.4132(2) 0.2585(2) 0.1090(9) Uani 0.408(2) 1 d P . . C11 C -0.2613(4) 0.32914(13) 0.12322(13) 0.0710(4) Uani 1 1 d . . . C12 C -0.3155(4) 0.23921(14) 0.17921(12) 0.0793(5) Uani 1 1 d . . . H12A H -0.4138 0.2406 0.2466 0.095 Uiso 1 1 calc R . . C13 C -0.2224(4) 0.14756(12) 0.13409(13) 0.0755(4) Uani 1 1 d . . . H13A H -0.2565 0.0866 0.1720 0.091 Uiso 1 1 calc R . . C14 C -0.0780(3) 0.14315(11) 0.03306(11) 0.0636(4) Uani 1 1 d . . . C15 C -0.0288(4) 0.23588(12) -0.02050(12) 0.0717(4) Uani 1 1 d . . . H15A H 0.0689 0.2349 -0.0880 0.086 Uiso 1 1 calc R . . C16 C -0.1199(4) 0.32925(12) 0.02300(13) 0.0758(4) Uani 1 1 d . . . H16A H -0.0866 0.3906 -0.0144 0.091 Uiso 1 1 calc R . . C17 C 0.0236(4) 0.04631(10) -0.01824(13) 0.0709(4) Uani 1 1 d . . . H17 H 0.1328 0.0519 -0.0835 0.085 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1103(11) 0.092(2) 0.1309(19) -0.044(2) 0.0059(12) 0.0209(17) N11 0.083(3) 0.065(4) 0.117(4) -0.002(4) -0.010(3) 0.005(3) O11 0.163(3) 0.067(2) 0.138(4) 0.0076(19) 0.041(2) 0.0115(19) O12 0.147(2) 0.0900(19) 0.0938(19) -0.0274(16) 0.0374(18) 0.0164(16) C1 0.0577(9) 0.0796(12) 0.0750(11) -0.0150(9) -0.0024(8) 0.0057(8) C2 0.0694(10) 0.1039(13) 0.0652(10) -0.0035(10) 0.0095(8) -0.0006(9) C3 0.0681(10) 0.0814(11) 0.0773(11) 0.0096(9) 0.0066(8) -0.0043(8) C4 0.0513(8) 0.0747(10) 0.0644(10) -0.0042(8) 0.0002(7) -0.0009(7) C5 0.0682(10) 0.0828(11) 0.0644(9) 0.0011(9) 0.0082(8) -0.0014(8) C6 0.0747(10) 0.0752(11) 0.0774(11) 0.0027(9) 0.0040(9) 0.0020(8) C7 0.0626(9) 0.0798(11) 0.0704(10) 0.0041(8) 0.0052(7) -0.0023(8) Cl11 0.1103(11) 0.092(2) 0.1309(19) -0.044(2) 0.0059(12) 0.0209(17) N1 0.083(3) 0.065(4) 0.117(4) -0.002(4) -0.010(3) 0.005(3) O1 0.163(3) 0.067(2) 0.138(4) 0.0076(19) 0.041(2) 0.0115(19) O2 0.147(2) 0.0900(19) 0.0938(19) -0.0274(16) 0.0374(18) 0.0164(16) C11 0.0577(9) 0.0796(12) 0.0750(11) -0.0150(9) -0.0024(8) 0.0057(8) C12 0.0694(10) 0.1039(13) 0.0652(10) -0.0035(10) 0.0095(8) -0.0006(9) C13 0.0681(10) 0.0814(11) 0.0773(11) 0.0096(9) 0.0066(8) -0.0043(8) C14 0.0513(8) 0.0747(10) 0.0644(10) -0.0042(8) 0.0002(7) -0.0009(7) C15 0.0682(10) 0.0828(11) 0.0644(9) 0.0011(9) 0.0082(8) -0.0014(8) C16 0.0747(10) 0.0752(11) 0.0774(11) 0.0027(9) 0.0040(9) 0.0020(8) C17 0.0626(9) 0.0798(11) 0.0704(10) 0.0041(8) 0.0052(7) -0.0023(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.583(5) . ? Cl1 O11 0.839(4) . ? Cl1 O12 1.315(4) . ? Cl1 C1 1.868(2) . ? N11 O12 1.197(9) . ? N11 O11 1.256(9) . ? N11 C1 1.345(5) . ? C1 C6 1.374(2) . ? C1 C2 1.374(2) . ? C2 C3 1.368(2) . ? C2 H2A 0.9300 . ? C3 C4 1.3893(19) . ? C3 H3A 0.9300 . ? C4 C5 1.3874(19) . ? C4 C7 1.4680(19) . ? C5 C6 1.3770(18) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.297(2) . ? C7 H7 0.9300 . ? Cl11 N1 0.583(5) . ? Cl11 O1 0.839(4) . ? Cl11 O2 1.315(4) . ? Cl11 C11 1.868(2) . ? N1 O2 1.197(9) . ? N1 O1 1.256(9) . ? N1 C11 1.345(5) . ? C11 C16 1.374(2) . ? C11 C12 1.374(2) . ? C12 C13 1.368(2) . ? C12 H12A 0.9300 . ? C13 C14 1.3893(19) . ? C13 H13A 0.9300 . ? C14 C15 1.3874(19) . ? C14 C17 1.4680(19) . ? C15 C16 1.3770(18) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 123.1(14) . . ? N11 Cl1 O12 65.5(11) . . ? O11 Cl1 O12 169.8(5) . . ? N11 Cl1 C1 22.0(11) . . ? O11 Cl1 C1 101.5(4) . . ? O12 Cl1 C1 87.36(16) . . ? Cl1 N11 O12 88.2(11) . . ? Cl1 N11 O11 34.0(10) . . ? O12 N11 O11 122.0(5) . . ? Cl1 N11 C1 148.7(15) . . ? O12 N11 C1 122.9(6) . . ? O11 N11 C1 115.0(7) . . ? Cl1 O11 N11 22.9(5) . . ? N11 O12 Cl1 26.3(2) . . ? N11 C1 C6 123.7(4) . . ? N11 C1 C2 114.5(4) . . ? C6 C1 C2 121.82(16) . . ? N11 C1 Cl1 9.3(5) . . ? C6 C1 Cl1 114.49(18) . . ? C2 C1 Cl1 123.69(17) . . ? C3 C2 C1 118.86(15) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C2 C3 C4 121.75(15) . . ? C2 C3 H3A 119.1 . . ? C4 C3 H3A 119.1 . . ? C5 C4 C3 117.33(15) . . ? C5 C4 C7 119.34(13) . . ? C3 C4 C7 123.33(15) . . ? C6 C5 C4 122.17(15) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C1 C6 C5 118.06(16) . . ? C1 C6 H6A 121.0 . . ? C5 C6 H6A 121.0 . . ? C17 C7 C4 126.61(19) . . ? C17 C7 H7 116.7 . . ? C4 C7 H7 116.7 . . ? N1 Cl11 O1 123.1(14) . . ? N1 Cl11 O2 65.5(11) . . ? O1 Cl11 O2 169.8(5) . . ? N1 Cl11 C11 22.0(11) . . ? O1 Cl11 C11 101.5(4) . . ? O2 Cl11 C11 87.36(16) . . ? Cl11 N1 O2 88.2(11) . . ? Cl11 N1 O1 34.0(10) . . ? O2 N1 O1 122.0(5) . . ? Cl11 N1 C11 148.7(15) . . ? O2 N1 C11 122.9(6) . . ? O1 N1 C11 115.0(7) . . ? Cl11 O1 N1 22.9(5) . . ? N1 O2 Cl11 26.3(2) . . ? N1 C11 C16 123.7(4) . . ? N1 C11 C12 114.5(4) . . ? C16 C11 C12 121.82(16) . . ? N1 C11 Cl11 9.3(5) . . ? C16 C11 Cl11 114.49(18) . . ? C12 C11 Cl11 123.69(17) . . ? C13 C12 C11 118.86(15) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? C12 C13 C14 121.75(15) . . ? C12 C13 H13A 119.1 . . ? C14 C13 H13A 119.1 . . ? C15 C14 C13 117.33(15) . . ? C15 C14 C17 119.34(13) . . ? C13 C14 C17 123.33(15) . . ? C16 C15 C14 122.17(15) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C11 C16 C15 118.06(16) . . ? C11 C16 H16A 121.0 . . ? C15 C16 H16A 121.0 . . ? C7 C17 C14 126.61(19) . . ? C7 C17 H17 116.7 . . ? C14 C17 H17 116.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 173.7(7) . . . . ? C1 Cl1 N11 O12 -175(3) . . . . ? O12 Cl1 N11 O11 -173.7(7) . . . . ? C1 Cl1 N11 O11 11(3) . . . . ? O11 Cl1 N11 C1 -11(3) . . . . ? O12 Cl1 N11 C1 175(3) . . . . ? O12 Cl1 O11 N11 145(4) . . . . ? C1 Cl1 O11 N11 -4.2(12) . . . . ? O12 N11 O11 Cl1 -7.5(9) . . . . ? C1 N11 O11 Cl1 173.6(18) . . . . ? O11 N11 O12 Cl1 4.2(5) . . . . ? C1 N11 O12 Cl1 -177.0(17) . . . . ? O11 Cl1 O12 N11 -149(4) . . . . ? C1 Cl1 O12 N11 1.8(10) . . . . ? Cl1 N11 C1 C6 9(3) . . . . ? O12 N11 C1 C6 -176.5(5) . . . . ? O11 N11 C1 C6 2.5(9) . . . . ? Cl1 N11 C1 C2 -172(2) . . . . ? O12 N11 C1 C2 2.1(9) . . . . ? O11 N11 C1 C2 -179.0(6) . . . . ? O12 N11 C1 Cl1 174(3) . . . . ? O11 N11 C1 Cl1 -7(2) . . . . ? O11 Cl1 C1 N11 170(3) . . . . ? O12 Cl1 C1 N11 -4(3) . . . . ? N11 Cl1 C1 C6 -171(3) . . . . ? O11 Cl1 C1 C6 -1.0(5) . . . . ? O12 Cl1 C1 C6 -175.90(18) . . . . ? N11 Cl1 C1 C2 9(3) . . . . ? O11 Cl1 C1 C2 179.1(4) . . . . ? O12 Cl1 C1 C2 4.2(3) . . . . ? N11 C1 C2 C3 -179.2(4) . . . . ? C6 C1 C2 C3 -0.7(2) . . . . ? Cl1 C1 C2 C3 179.22(16) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C5 -0.5(2) . . . . ? C2 C3 C4 C7 179.67(13) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? C7 C4 C5 C6 -179.72(13) . . . . ? N11 C1 C6 C5 179.1(4) . . . . ? C2 C1 C6 C5 0.6(2) . . . . ? Cl1 C1 C6 C5 -179.28(15) . . . . ? C4 C5 C6 C1 -0.5(2) . . . . ? C5 C4 C7 C17 175.74(19) . . . . ? C3 C4 C7 C17 -4.4(3) . . . . ? O1 Cl11 N1 O2 -173.7(7) . . . . ? C11 Cl11 N1 O2 175(3) . . . . ? O2 Cl11 N1 O1 173.7(7) . . . . ? C11 Cl11 N1 O1 -11(3) . . . . ? O1 Cl11 N1 C11 11(3) . . . . ? O2 Cl11 N1 C11 -175(3) . . . . ? O2 Cl11 O1 N1 -145(4) . . . . ? C11 Cl11 O1 N1 4.2(12) . . . . ? O2 N1 O1 Cl11 7.5(9) . . . . ? C11 N1 O1 Cl11 -173.6(18) . . . . ? O1 N1 O2 Cl11 -4.2(5) . . . . ? C11 N1 O2 Cl11 177.0(17) . . . . ? O1 Cl11 O2 N1 149(4) . . . . ? C11 Cl11 O2 N1 -1.8(10) . . . . ? Cl11 N1 C11 C16 -9(3) . . . . ? O2 N1 C11 C16 176.5(5) . . . . ? O1 N1 C11 C16 -2.5(9) . . . . ? Cl11 N1 C11 C12 172(2) . . . . ? O2 N1 C11 C12 -2.1(9) . . . . ? O1 N1 C11 C12 179.0(6) . . . . ? O2 N1 C11 Cl11 -174(3) . . . . ? O1 N1 C11 Cl11 7(2) . . . . ? O1 Cl11 C11 N1 -170(3) . . . . ? O2 Cl11 C11 N1 4(3) . . . . ? N1 Cl11 C11 C16 171(3) . . . . ? O1 Cl11 C11 C16 1.0(5) . . . . ? O2 Cl11 C11 C16 175.90(18) . . . . ? N1 Cl11 C11 C12 -9(3) . . . . ? O1 Cl11 C11 C12 -179.1(4) . . . . ? O2 Cl11 C11 C12 -4.2(3) . . . . ? N1 C11 C12 C13 179.2(4) . . . . ? C16 C11 C12 C13 0.7(2) . . . . ? Cl11 C11 C12 C13 -179.22(16) . . . . ? C11 C12 C13 C14 -0.6(2) . . . . ? C12 C13 C14 C15 0.5(2) . . . . ? C12 C13 C14 C17 -179.67(13) . . . . ? C13 C14 C15 C16 -0.4(2) . . . . ? C17 C14 C15 C16 179.72(13) . . . . ? N1 C11 C16 C15 -179.1(4) . . . . ? C12 C11 C16 C15 -0.6(2) . . . . ? Cl11 C11 C16 C15 179.28(15) . . . . ? C14 C15 C16 C11 0.5(2) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.74(19) . . . . ? C13 C14 C17 C7 4.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.901 _refine_diff_density_max 0.092 _refine_diff_density_min -0.102 _refine_diff_density_rms 0.022 # start Validation Reply Form _vrf_SYMMG02_CNS-ClBzIII-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-ClBzIII-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.90 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:23. ; # end Validation Reply Form #===END data_CNS-ClBzIV-small-P21_c _database_code_depnum_ccdc_archive 'CCDC 761206' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9100(2) _cell_length_b 12.9349(7) _cell_length_c 12.2210(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.352(2) _cell_angle_gamma 90.00 _cell_volume 617.03(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3454 _cell_measurement_theta_min 3.150 _cell_measurement_theta_max 24.4535 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.301 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.664592 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3444 _diffrn_reflns_av_R_equivalents 0.0125 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.75 _reflns_number_total 2304 _reflns_number_gt 1308 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0256P)^2^+0.1186P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 2304 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1046 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1092 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.180 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3716(12) -0.46044(14) -0.1747(4) 0.1147(17) Uani 0.50 1 d P . . N11 N 0.359(3) -0.4167(6) -0.1737(10) 0.0816(19) Uani 0.50 1 d P . . O11 O 0.3137(17) -0.4982(5) -0.1233(4) 0.130(2) Uani 0.50 1 d P . . O12 O 0.5006(9) -0.4124(2) -0.2585(3) 0.1098(11) Uani 0.50 1 d P . . C1 C 0.2609(4) -0.32909(14) -0.12340(16) 0.0703(5) Uani 1 1 d . . . C2 C 0.3153(4) -0.23905(17) -0.17892(14) 0.0805(5) Uani 1 1 d . . . H2A H 0.4144 -0.2405 -0.2463 0.097 Uiso 1 1 calc R . . C3 C 0.2225(4) -0.14726(14) -0.13421(15) 0.0736(5) Uani 1 1 d . . . H3A H 0.2564 -0.0862 -0.1722 0.088 Uiso 1 1 calc R . . C4 C 0.0782(4) -0.14334(13) -0.03282(14) 0.0648(5) Uani 1 1 d . . . C5 C 0.0290(4) -0.23594(13) 0.02063(14) 0.0715(5) Uani 1 1 d . . . H5A H -0.0684 -0.2350 0.0882 0.086 Uiso 1 1 calc R . . C6 C 0.1198(4) -0.32952(13) -0.02307(15) 0.0760(5) Uani 1 1 d . . . H6A H 0.0865 -0.3911 0.0142 0.091 Uiso 1 1 calc R . . C7 C -0.0234(4) -0.04645(11) 0.01832(15) 0.0716(5) Uani 1 1 d . . . H7 H -0.1326 -0.0521 0.0836 0.086 Uiso 1 1 calc R . . Cl11 Cl -0.3716(12) 0.46044(14) 0.1747(4) 0.1147(17) Uani 0.50 1 d P . . N1 N -0.359(3) 0.4167(6) 0.1737(10) 0.0816(19) Uani 0.50 1 d P . . O1 O -0.3137(17) 0.4982(5) 0.1233(4) 0.130(2) Uani 0.50 1 d P . . O2 O -0.5006(9) 0.4124(2) 0.2585(3) 0.1098(11) Uani 0.50 1 d P . . C11 C -0.2609(4) 0.32909(14) 0.12340(16) 0.0703(5) Uani 1 1 d . . . C12 C -0.3153(4) 0.23905(17) 0.17892(14) 0.0805(5) Uani 1 1 d . . . H12A H -0.4144 0.2405 0.2463 0.097 Uiso 1 1 calc R . . C13 C -0.2225(4) 0.14726(14) 0.13421(15) 0.0736(5) Uani 1 1 d . . . H13A H -0.2564 0.0862 0.1722 0.088 Uiso 1 1 calc R . . C14 C -0.0782(4) 0.14334(13) 0.03282(14) 0.0648(5) Uani 1 1 d . . . C15 C -0.0290(4) 0.23594(13) -0.02063(14) 0.0715(5) Uani 1 1 d . . . H15A H 0.0684 0.2350 -0.0882 0.086 Uiso 1 1 calc R . . C16 C -0.1198(4) 0.32952(13) 0.02307(15) 0.0760(5) Uani 1 1 d . . . H16A H -0.0865 0.3911 -0.0142 0.091 Uiso 1 1 calc R . . C17 C 0.0234(4) 0.04645(11) -0.01832(15) 0.0716(5) Uani 1 1 d . . . H17 H 0.1326 0.0521 -0.0836 0.086 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1146(14) 0.092(3) 0.137(3) -0.047(3) 0.0005(17) 0.027(2) N11 0.076(3) 0.068(5) 0.101(5) 0.003(5) 0.002(3) 0.012(4) O11 0.176(4) 0.070(3) 0.149(5) 0.005(3) 0.037(3) 0.013(2) O12 0.150(3) 0.087(2) 0.096(2) -0.0257(19) 0.032(2) 0.0157(19) C1 0.0594(11) 0.0772(13) 0.0738(13) -0.0163(10) -0.0011(9) 0.0049(9) C2 0.0691(12) 0.1053(15) 0.0676(12) -0.0042(11) 0.0085(10) -0.0006(11) C3 0.0694(12) 0.0778(13) 0.0742(13) 0.0086(10) 0.0087(10) -0.0025(9) C4 0.0522(10) 0.0751(12) 0.0665(12) -0.0051(10) -0.0005(8) -0.0012(8) C5 0.0697(11) 0.0814(13) 0.0638(11) 0.0013(10) 0.0076(9) -0.0026(10) C6 0.0760(12) 0.0737(13) 0.0780(13) 0.0009(10) 0.0027(10) 0.0045(9) C7 0.0634(11) 0.0797(12) 0.0718(12) 0.0044(10) 0.0051(9) -0.0023(10) Cl11 0.1146(14) 0.092(3) 0.137(3) -0.047(3) 0.0005(17) 0.027(2) N1 0.076(3) 0.068(5) 0.101(5) 0.003(5) 0.002(3) 0.012(4) O1 0.176(4) 0.070(3) 0.149(5) 0.005(3) 0.037(3) 0.013(2) O2 0.150(3) 0.087(2) 0.096(2) -0.0257(19) 0.032(2) 0.0157(19) C11 0.0594(11) 0.0772(13) 0.0738(13) -0.0163(10) -0.0011(9) 0.0049(9) C12 0.0691(12) 0.1053(15) 0.0676(12) -0.0042(11) 0.0085(10) -0.0006(11) C13 0.0694(12) 0.0778(13) 0.0742(13) 0.0086(10) 0.0087(10) -0.0025(9) C14 0.0522(10) 0.0751(12) 0.0665(12) -0.0051(10) -0.0005(8) -0.0012(8) C15 0.0697(11) 0.0814(13) 0.0638(11) 0.0013(10) 0.0076(9) -0.0026(10) C16 0.0760(12) 0.0737(13) 0.0780(13) 0.0009(10) 0.0027(10) 0.0045(9) C17 0.0634(11) 0.0797(12) 0.0718(12) 0.0044(10) 0.0051(9) -0.0023(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.569(7) . ? Cl1 O11 0.837(5) . ? Cl1 O12 1.322(6) . ? Cl1 C1 1.870(3) . ? N11 O12 1.204(13) . ? N11 O11 1.239(14) . ? N11 C1 1.355(6) . ? C1 C2 1.371(2) . ? C1 C6 1.374(2) . ? C2 C3 1.365(2) . ? C2 H2A 0.9300 . ? C3 C4 1.392(2) . ? C3 H3A 0.9300 . ? C4 C5 1.383(2) . ? C4 C7 1.466(2) . ? C5 C6 1.378(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.299(3) . ? C7 H7 0.9300 . ? Cl11 N1 0.569(7) . ? Cl11 O1 0.837(5) . ? Cl11 O2 1.322(6) . ? Cl11 C11 1.870(3) . ? N1 O2 1.204(13) . ? N1 O1 1.239(14) . ? N1 C11 1.355(6) . ? C11 C12 1.371(2) . ? C11 C16 1.374(2) . ? C12 C13 1.365(2) . ? C12 H12A 0.9300 . ? C13 C14 1.392(2) . ? C13 H13A 0.9300 . ? C14 C15 1.383(2) . ? C14 C17 1.466(2) . ? C15 C16 1.378(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 122(2) . . ? N11 Cl1 O12 65.6(17) . . ? O11 Cl1 O12 170.7(7) . . ? N11 Cl1 C1 20.9(16) . . ? O11 Cl1 C1 101.6(7) . . ? O12 Cl1 C1 86.50(19) . . ? Cl1 N11 O12 89.0(16) . . ? Cl1 N11 O11 34.8(15) . . ? O12 N11 O11 123.5(6) . . ? Cl1 N11 C1 150(2) . . ? O12 N11 C1 120.6(8) . . ? O11 N11 C1 115.7(9) . . ? Cl1 O11 N11 22.8(7) . . ? N11 O12 Cl1 25.5(3) . . ? N11 C1 C2 115.4(6) . . ? N11 C1 C6 122.7(5) . . ? C2 C1 C6 121.82(18) . . ? N11 C1 Cl1 8.6(7) . . ? C2 C1 Cl1 124.1(2) . . ? C6 C1 Cl1 114.1(2) . . ? C3 C2 C1 119.23(18) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.27(18) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C5 C4 C3 117.62(17) . . ? C5 C4 C7 119.37(16) . . ? C3 C4 C7 123.01(17) . . ? C6 C5 C4 122.12(17) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C1 C6 C5 117.93(18) . . ? C1 C6 H6A 121.0 . . ? C5 C6 H6A 121.0 . . ? C17 C7 C4 126.6(2) . . ? C17 C7 H7 116.7 . . ? C4 C7 H7 116.7 . . ? N1 Cl11 O1 122(2) . . ? N1 Cl11 O2 65.6(17) . . ? O1 Cl11 O2 170.7(7) . . ? N1 Cl11 C11 20.9(16) . . ? O1 Cl11 C11 101.6(7) . . ? O2 Cl11 C11 86.50(19) . . ? Cl11 N1 O2 89.0(16) . . ? Cl11 N1 O1 34.8(15) . . ? O2 N1 O1 123.5(6) . . ? Cl11 N1 C11 150(2) . . ? O2 N1 C11 120.6(8) . . ? O1 N1 C11 115.7(9) . . ? Cl11 O1 N1 22.8(7) . . ? N1 O2 Cl11 25.5(3) . . ? N1 C11 C12 115.4(6) . . ? N1 C11 C16 122.7(5) . . ? C12 C11 C16 121.82(18) . . ? N1 C11 Cl11 8.6(7) . . ? C12 C11 Cl11 124.1(2) . . ? C16 C11 Cl11 114.1(2) . . ? C13 C12 C11 119.23(18) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 121.27(18) . . ? C12 C13 H13A 119.4 . . ? C14 C13 H13A 119.4 . . ? C15 C14 C13 117.62(17) . . ? C15 C14 C17 119.37(16) . . ? C13 C14 C17 123.01(17) . . ? C16 C15 C14 122.12(17) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C11 C16 C15 117.93(18) . . ? C11 C16 H16A 121.0 . . ? C15 C16 H16A 121.0 . . ? C7 C17 C14 126.6(2) . . ? C7 C17 H17 116.7 . . ? C14 C17 H17 116.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 174.8(10) . . . . ? C1 Cl1 N11 O12 178(4) . . . . ? O12 Cl1 N11 O11 -174.8(10) . . . . ? C1 Cl1 N11 O11 3(4) . . . . ? O11 Cl1 N11 C1 -3(4) . . . . ? O12 Cl1 N11 C1 -178(4) . . . . ? O12 Cl1 O11 N11 149(6) . . . . ? C1 Cl1 O11 N11 -1.1(16) . . . . ? O12 N11 O11 Cl1 -6.3(12) . . . . ? C1 N11 O11 Cl1 178(2) . . . . ? O11 N11 O12 Cl1 3.6(7) . . . . ? C1 N11 O12 Cl1 179(2) . . . . ? O11 Cl1 O12 N11 -152(5) . . . . ? C1 Cl1 O12 N11 -0.8(14) . . . . ? Cl1 N11 C1 C2 -179(3) . . . . ? O12 N11 C1 C2 3.8(10) . . . . ? O11 N11 C1 C2 179.3(7) . . . . ? Cl1 N11 C1 C6 2(4) . . . . ? O12 N11 C1 C6 -175.5(6) . . . . ? O11 N11 C1 C6 0.0(12) . . . . ? O12 N11 C1 Cl1 -177(4) . . . . ? O11 N11 C1 Cl1 -2(3) . . . . ? O11 Cl1 C1 N11 177(4) . . . . ? O12 Cl1 C1 N11 2(3) . . . . ? N11 Cl1 C1 C2 1(4) . . . . ? O11 Cl1 C1 C2 178.7(6) . . . . ? O12 Cl1 C1 C2 3.3(4) . . . . ? N11 Cl1 C1 C6 -178(4) . . . . ? O11 Cl1 C1 C6 -0.8(7) . . . . ? O12 Cl1 C1 C6 -176.2(2) . . . . ? N11 C1 C2 C3 179.7(5) . . . . ? C6 C1 C2 C3 -0.9(3) . . . . ? Cl1 C1 C2 C3 179.5(2) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C2 C3 C4 C7 179.70(16) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? C7 C4 C5 C6 -179.88(15) . . . . ? N11 C1 C6 C5 180.0(5) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? Cl1 C1 C6 C5 -179.70(19) . . . . ? C4 C5 C6 C1 -0.5(2) . . . . ? C5 C4 C7 C17 175.8(2) . . . . ? C3 C4 C7 C17 -4.5(3) . . . . ? O1 Cl11 N1 O2 -174.8(10) . . . . ? C11 Cl11 N1 O2 -178(4) . . . . ? O2 Cl11 N1 O1 174.8(10) . . . . ? C11 Cl11 N1 O1 -3(4) . . . . ? O1 Cl11 N1 C11 3(4) . . . . ? O2 Cl11 N1 C11 178(4) . . . . ? O2 Cl11 O1 N1 -149(6) . . . . ? C11 Cl11 O1 N1 1.1(16) . . . . ? O2 N1 O1 Cl11 6.3(12) . . . . ? C11 N1 O1 Cl11 -178(2) . . . . ? O1 N1 O2 Cl11 -3.6(7) . . . . ? C11 N1 O2 Cl11 -179(2) . . . . ? O1 Cl11 O2 N1 152(5) . . . . ? C11 Cl11 O2 N1 0.8(14) . . . . ? Cl11 N1 C11 C12 179(3) . . . . ? O2 N1 C11 C12 -3.8(10) . . . . ? O1 N1 C11 C12 -179.3(7) . . . . ? Cl11 N1 C11 C16 -2(4) . . . . ? O2 N1 C11 C16 175.5(6) . . . . ? O1 N1 C11 C16 0.0(12) . . . . ? O2 N1 C11 Cl11 177(4) . . . . ? O1 N1 C11 Cl11 2(3) . . . . ? O1 Cl11 C11 N1 -177(4) . . . . ? O2 Cl11 C11 N1 -2(3) . . . . ? N1 Cl11 C11 C12 -1(4) . . . . ? O1 Cl11 C11 C12 -178.7(6) . . . . ? O2 Cl11 C11 C12 -3.3(4) . . . . ? N1 Cl11 C11 C16 178(4) . . . . ? O1 Cl11 C11 C16 0.8(7) . . . . ? O2 Cl11 C11 C16 176.2(2) . . . . ? N1 C11 C12 C13 -179.7(5) . . . . ? C16 C11 C12 C13 0.9(3) . . . . ? Cl11 C11 C12 C13 -179.5(2) . . . . ? C11 C12 C13 C14 -0.9(3) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C12 C13 C14 C17 -179.70(16) . . . . ? C13 C14 C15 C16 -0.4(2) . . . . ? C17 C14 C15 C16 179.88(15) . . . . ? N1 C11 C16 C15 180.0(5) . . . . ? C12 C11 C16 C15 -0.7(3) . . . . ? Cl11 C11 C16 C15 179.70(19) . . . . ? C14 C15 C16 C11 0.5(2) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.8(2) . . . . ? C13 C14 C17 C7 4.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.879 _diffrn_reflns_theta_full 27.75 _diffrn_measured_fraction_theta_full 0.879 _refine_diff_density_max 0.084 _refine_diff_density_min -0.113 _refine_diff_density_rms 0.023 # start Validation Reply Form _vrf_SYMMG02_CNS-ClBzIV-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-ClBzIV-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.88 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:23. ; # end Validation Reply Form #===END data_CNS-ClBzIV-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761207' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9100(2) _cell_length_b 12.9349(7) _cell_length_c 12.2210(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.352(2) _cell_angle_gamma 90.00 _cell_volume 617.03(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3454 _cell_measurement_theta_min 3.150 _cell_measurement_theta_max 24.4535 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.301 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.664592 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3444 _diffrn_reflns_av_R_equivalents 0.0125 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.75 _reflns_number_total 2304 _reflns_number_gt 1308 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0256P)^2^+0.1186P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(2) _refine_ls_number_reflns 2304 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0968 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3712(9) -0.46022(12) -0.1753(3) 0.1141(12) Uani 0.409(2) 1 d P . . N11 N 0.361(2) -0.4163(4) -0.1729(7) 0.0840(16) Uani 0.591(2) 1 d P . . O11 O 0.3129(14) -0.4979(3) -0.1236(4) 0.1263(18) Uani 0.591(2) 1 d P . . O12 O 0.5012(8) -0.4128(2) -0.2586(2) 0.1090(9) Uani 0.591(2) 1 d P . . C1 C 0.2613(4) -0.32930(13) -0.12341(14) 0.0708(4) Uani 1 1 d . . . C2 C 0.3154(4) -0.23902(14) -0.17914(13) 0.0796(5) Uani 1 1 d . . . H2A H 0.4140 -0.2404 -0.2466 0.095 Uiso 1 1 calc R . . C3 C 0.2224(4) -0.14734(12) -0.13414(13) 0.0744(5) Uani 1 1 d . . . H3A H 0.2563 -0.0862 -0.1721 0.089 Uiso 1 1 calc R . . C4 C 0.0783(3) -0.14309(11) -0.03302(12) 0.0642(4) Uani 1 1 d . . . C5 C 0.0293(4) -0.23601(12) 0.02063(13) 0.0718(4) Uani 1 1 d . . . H5A H -0.0682 -0.2351 0.0882 0.086 Uiso 1 1 calc R . . C6 C 0.1202(4) -0.32930(12) -0.02307(13) 0.0759(5) Uani 1 1 d . . . H6A H 0.0870 -0.3908 0.0143 0.091 Uiso 1 1 calc R . . C7 C -0.0234(4) -0.04642(10) 0.01822(13) 0.0710(4) Uani 1 1 d . . . H7 H -0.1327 -0.0521 0.0835 0.085 Uiso 1 1 calc R . . Cl11 Cl -0.3712(9) 0.46022(12) 0.1753(3) 0.1141(12) Uani 0.591(2) 1 d P . . N1 N -0.361(2) 0.4163(4) 0.1729(7) 0.0840(16) Uani 0.409(2) 1 d P . . O1 O -0.3129(14) 0.4979(3) 0.1236(4) 0.1263(18) Uani 0.409(2) 1 d P . . O2 O -0.5012(8) 0.4128(2) 0.2586(2) 0.1090(9) Uani 0.409(2) 1 d P . . C11 C -0.2613(4) 0.32930(13) 0.12341(14) 0.0708(4) Uani 1 1 d . . . C12 C -0.3154(4) 0.23902(14) 0.17914(13) 0.0796(5) Uani 1 1 d . . . H12A H -0.4140 0.2404 0.2466 0.095 Uiso 1 1 calc R . . C13 C -0.2224(4) 0.14734(12) 0.13414(13) 0.0744(5) Uani 1 1 d . . . H13A H -0.2563 0.0862 0.1721 0.089 Uiso 1 1 calc R . . C14 C -0.0783(3) 0.14309(11) 0.03302(12) 0.0642(4) Uani 1 1 d . . . C15 C -0.0293(4) 0.23601(12) -0.02063(13) 0.0718(4) Uani 1 1 d . . . H15A H 0.0682 0.2351 -0.0882 0.086 Uiso 1 1 calc R . . C16 C -0.1202(4) 0.32930(12) 0.02307(13) 0.0759(5) Uani 1 1 d . . . H16A H -0.0870 0.3908 -0.0143 0.091 Uiso 1 1 calc R . . C17 C 0.0234(4) 0.04642(10) -0.01822(13) 0.0710(4) Uani 1 1 d . . . H17 H 0.1327 0.0521 -0.0835 0.085 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1129(12) 0.093(2) 0.136(2) -0.047(2) 0.0023(13) 0.0246(18) N11 0.079(3) 0.068(4) 0.103(4) -0.003(4) -0.004(3) 0.010(3) O11 0.170(3) 0.068(2) 0.144(4) 0.007(2) 0.039(3) 0.012(2) O12 0.150(3) 0.0865(18) 0.0941(19) -0.0237(16) 0.0356(18) 0.0149(16) C1 0.0583(10) 0.0796(12) 0.0739(11) -0.0161(9) -0.0011(8) 0.0050(8) C2 0.0691(11) 0.1032(13) 0.0670(11) -0.0037(10) 0.0091(8) -0.0006(9) C3 0.0688(10) 0.0792(11) 0.0756(11) 0.0095(9) 0.0073(9) -0.0034(8) C4 0.0526(9) 0.0753(10) 0.0643(10) -0.0046(8) 0.0001(7) -0.0009(7) C5 0.0694(10) 0.0822(11) 0.0642(10) 0.0018(9) 0.0075(8) -0.0020(8) C6 0.0760(11) 0.0739(11) 0.0776(12) 0.0007(9) 0.0033(9) 0.0033(8) C7 0.0632(9) 0.0787(11) 0.0713(10) 0.0040(8) 0.0048(8) -0.0021(8) Cl11 0.1129(12) 0.093(2) 0.136(2) -0.047(2) 0.0023(13) 0.0246(18) N1 0.079(3) 0.068(4) 0.103(4) -0.003(4) -0.004(3) 0.010(3) O1 0.170(3) 0.068(2) 0.144(4) 0.007(2) 0.039(3) 0.012(2) O2 0.150(3) 0.0865(18) 0.0941(19) -0.0237(16) 0.0356(18) 0.0149(16) C11 0.0583(10) 0.0796(12) 0.0739(11) -0.0161(9) -0.0011(8) 0.0050(8) C12 0.0691(11) 0.1032(13) 0.0670(11) -0.0037(10) 0.0091(8) -0.0006(9) C13 0.0688(10) 0.0792(11) 0.0756(11) 0.0095(9) 0.0073(9) -0.0034(8) C14 0.0526(9) 0.0753(10) 0.0643(10) -0.0046(8) 0.0001(7) -0.0009(7) C15 0.0694(10) 0.0822(11) 0.0642(10) 0.0018(9) 0.0075(8) -0.0020(8) C16 0.0760(11) 0.0739(11) 0.0776(12) 0.0007(9) 0.0033(9) 0.0033(8) C17 0.0632(9) 0.0787(11) 0.0713(10) 0.0040(8) 0.0048(8) -0.0021(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.571(6) . ? Cl1 O11 0.840(4) . ? Cl1 O12 1.316(4) . ? Cl1 C1 1.867(2) . ? N11 O12 1.211(9) . ? N11 O11 1.236(10) . ? N11 C1 1.346(5) . ? C1 C6 1.374(2) . ? C1 C2 1.374(2) . ? C2 C3 1.365(2) . ? C2 H2A 0.9300 . ? C3 C4 1.389(2) . ? C3 H3A 0.9300 . ? C4 C5 1.3878(19) . ? C4 C7 1.4639(19) . ? C5 C6 1.3748(18) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.297(2) . ? C7 H7 0.9300 . ? Cl11 N1 0.571(6) . ? Cl11 O1 0.840(4) . ? Cl11 O2 1.316(4) . ? Cl11 C11 1.867(2) . ? N1 O2 1.211(9) . ? N1 O1 1.236(10) . ? N1 C11 1.346(5) . ? C11 C16 1.374(2) . ? C11 C12 1.374(2) . ? C12 C13 1.365(2) . ? C12 H12A 0.9300 . ? C13 C14 1.389(2) . ? C13 H13A 0.9300 . ? C14 C15 1.3878(19) . ? C14 C17 1.4639(19) . ? C15 C16 1.3748(18) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 121.1(15) . . ? N11 Cl1 O12 66.9(12) . . ? O11 Cl1 O12 170.6(5) . . ? N11 Cl1 C1 20.1(11) . . ? O11 Cl1 C1 101.1(5) . . ? O12 Cl1 C1 86.97(17) . . ? Cl1 N11 O12 87.5(11) . . ? Cl1 N11 O11 35.6(11) . . ? O12 N11 O11 122.9(5) . . ? Cl1 N11 C1 151.5(16) . . ? O12 N11 C1 121.0(6) . . ? O11 N11 C1 116.0(6) . . ? Cl1 O11 N11 23.3(5) . . ? N11 O12 Cl1 25.7(3) . . ? N11 C1 C6 122.9(4) . . ? N11 C1 C2 115.5(4) . . ? C6 C1 C2 121.59(16) . . ? N11 C1 Cl1 8.4(5) . . ? C6 C1 Cl1 114.56(19) . . ? C2 C1 Cl1 123.85(18) . . ? C3 C2 C1 119.07(15) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 121.61(16) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C5 C4 C3 117.43(15) . . ? C5 C4 C7 119.28(14) . . ? C3 C4 C7 123.29(15) . . ? C6 C5 C4 122.04(15) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C1 C6 C5 118.24(16) . . ? C1 C6 H6A 120.9 . . ? C5 C6 H6A 120.9 . . ? C17 C7 C4 126.6(2) . . ? C17 C7 H7 116.7 . . ? C4 C7 H7 116.7 . . ? N1 Cl11 O1 121.1(15) . . ? N1 Cl11 O2 66.9(12) . . ? O1 Cl11 O2 170.6(5) . . ? N1 Cl11 C11 20.1(11) . . ? O1 Cl11 C11 101.1(5) . . ? O2 Cl11 C11 86.97(17) . . ? Cl11 N1 O2 87.5(11) . . ? Cl11 N1 O1 35.6(11) . . ? O2 N1 O1 122.9(5) . . ? Cl11 N1 C11 151.5(16) . . ? O2 N1 C11 121.0(6) . . ? O1 N1 C11 116.0(6) . . ? Cl11 O1 N1 23.3(5) . . ? N1 O2 Cl11 25.7(3) . . ? N1 C11 C16 122.9(4) . . ? N1 C11 C12 115.5(4) . . ? C16 C11 C12 121.59(16) . . ? N1 C11 Cl11 8.4(5) . . ? C16 C11 Cl11 114.56(19) . . ? C12 C11 Cl11 123.85(18) . . ? C13 C12 C11 119.07(15) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C14 121.61(16) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C15 C14 C13 117.43(15) . . ? C15 C14 C17 119.28(14) . . ? C13 C14 C17 123.29(15) . . ? C16 C15 C14 122.04(15) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C11 C16 C15 118.24(16) . . ? C11 C16 H16A 120.9 . . ? C15 C16 H16A 120.9 . . ? C7 C17 C14 126.6(2) . . ? C7 C17 H17 116.7 . . ? C14 C17 H17 116.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 174.3(8) . . . . ? C1 Cl1 N11 O12 -178(3) . . . . ? O12 Cl1 N11 O11 -174.3(8) . . . . ? C1 Cl1 N11 O11 8(4) . . . . ? O11 Cl1 N11 C1 -8(4) . . . . ? O12 Cl1 N11 C1 178(3) . . . . ? O12 Cl1 O11 N11 146(4) . . . . ? C1 Cl1 O11 N11 -2.6(13) . . . . ? O12 N11 O11 Cl1 -6.8(9) . . . . ? C1 N11 O11 Cl1 176(2) . . . . ? O11 N11 O12 Cl1 3.9(5) . . . . ? C1 N11 O12 Cl1 -179.0(18) . . . . ? O11 Cl1 O12 N11 -149(4) . . . . ? C1 Cl1 O12 N11 0.6(11) . . . . ? Cl1 N11 C1 C6 6(3) . . . . ? O12 N11 C1 C6 -176.0(5) . . . . ? O11 N11 C1 C6 1.3(10) . . . . ? Cl1 N11 C1 C2 -175(3) . . . . ? O12 N11 C1 C2 2.9(9) . . . . ? O11 N11 C1 C2 -179.9(6) . . . . ? O12 N11 C1 Cl1 178(4) . . . . ? O11 N11 C1 Cl1 -5(2) . . . . ? O11 Cl1 C1 N11 173(3) . . . . ? O12 Cl1 C1 N11 -2(3) . . . . ? N11 Cl1 C1 C6 -174(3) . . . . ? O11 Cl1 C1 C6 -0.9(5) . . . . ? O12 Cl1 C1 C6 -176.03(19) . . . . ? N11 Cl1 C1 C2 5(3) . . . . ? O11 Cl1 C1 C2 178.9(5) . . . . ? O12 Cl1 C1 C2 3.8(3) . . . . ? N11 C1 C2 C3 -179.7(4) . . . . ? C6 C1 C2 C3 -0.8(2) . . . . ? Cl1 C1 C2 C3 179.38(18) . . . . ? C1 C2 C3 C4 0.8(2) . . . . ? C2 C3 C4 C5 -0.5(2) . . . . ? C2 C3 C4 C7 179.72(14) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? C7 C4 C5 C6 -179.84(13) . . . . ? N11 C1 C6 C5 179.5(4) . . . . ? C2 C1 C6 C5 0.7(2) . . . . ? Cl1 C1 C6 C5 -179.49(16) . . . . ? C4 C5 C6 C1 -0.5(2) . . . . ? C5 C4 C7 C17 175.76(19) . . . . ? C3 C4 C7 C17 -4.5(3) . . . . ? O1 Cl11 N1 O2 -174.3(8) . . . . ? C11 Cl11 N1 O2 178(3) . . . . ? O2 Cl11 N1 O1 174.3(8) . . . . ? C11 Cl11 N1 O1 -8(4) . . . . ? O1 Cl11 N1 C11 8(4) . . . . ? O2 Cl11 N1 C11 -178(3) . . . . ? O2 Cl11 O1 N1 -146(4) . . . . ? C11 Cl11 O1 N1 2.6(13) . . . . ? O2 N1 O1 Cl11 6.8(9) . . . . ? C11 N1 O1 Cl11 -176(2) . . . . ? O1 N1 O2 Cl11 -3.9(5) . . . . ? C11 N1 O2 Cl11 179.0(18) . . . . ? O1 Cl11 O2 N1 149(4) . . . . ? C11 Cl11 O2 N1 -0.6(11) . . . . ? Cl11 N1 C11 C16 -6(3) . . . . ? O2 N1 C11 C16 176.0(5) . . . . ? O1 N1 C11 C16 -1.3(10) . . . . ? Cl11 N1 C11 C12 175(3) . . . . ? O2 N1 C11 C12 -2.9(9) . . . . ? O1 N1 C11 C12 179.9(6) . . . . ? O2 N1 C11 Cl11 -178(4) . . . . ? O1 N1 C11 Cl11 5(2) . . . . ? O1 Cl11 C11 N1 -173(3) . . . . ? O2 Cl11 C11 N1 2(3) . . . . ? N1 Cl11 C11 C16 174(3) . . . . ? O1 Cl11 C11 C16 0.9(5) . . . . ? O2 Cl11 C11 C16 176.03(19) . . . . ? N1 Cl11 C11 C12 -5(3) . . . . ? O1 Cl11 C11 C12 -178.9(5) . . . . ? O2 Cl11 C11 C12 -3.8(3) . . . . ? N1 C11 C12 C13 179.7(4) . . . . ? C16 C11 C12 C13 0.8(2) . . . . ? Cl11 C11 C12 C13 -179.38(18) . . . . ? C11 C12 C13 C14 -0.8(2) . . . . ? C12 C13 C14 C15 0.5(2) . . . . ? C12 C13 C14 C17 -179.72(14) . . . . ? C13 C14 C15 C16 -0.4(2) . . . . ? C17 C14 C15 C16 179.84(13) . . . . ? N1 C11 C16 C15 -179.5(4) . . . . ? C12 C11 C16 C15 -0.7(2) . . . . ? Cl11 C11 C16 C15 179.49(16) . . . . ? C14 C15 C16 C11 0.5(2) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.76(19) . . . . ? C13 C14 C17 C7 4.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 27.75 _diffrn_measured_fraction_theta_full 0.917 _refine_diff_density_max 0.094 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.023 # start Validation Reply Form _vrf_SYMMG02_CNS-ClBzIV-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-ClBzIV-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.92 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:23. ; # end Validation Reply Form #===END data_CNS-ClTol-small-P21_c _database_code_depnum_ccdc_archive 'CCDC 761208' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9182(2) _cell_length_b 12.9555(8) _cell_length_c 12.2381(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.254(3) _cell_angle_gamma 90.00 _cell_volume 620.23(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3482 _cell_measurement_theta_min 3.145 _cell_measurement_theta_max 23.011 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.117740 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3447 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.84 _reflns_number_total 2541 _reflns_number_gt 1202 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0999P)^2^+0.1114P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2541 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1507 _refine_ls_R_factor_gt 0.0750 _refine_ls_wR_factor_ref 0.2512 _refine_ls_wR_factor_gt 0.2164 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.371(2) -0.4615(2) -0.1752(7) 0.133(3) Uani 0.50 1 d P . . N11 N 0.360(3) -0.4205(9) -0.1716(11) 0.081(2) Uani 0.50 1 d P . . O11 O 0.308(3) -0.4948(9) -0.1225(7) 0.148(3) Uani 0.50 1 d P . . O12 O 0.4992(14) -0.4115(4) -0.2587(4) 0.1211(19) Uani 0.50 1 d P . . C1 C 0.2604(6) -0.3291(2) -0.1235(2) 0.0767(8) Uani 1 1 d . . . C2 C 0.3157(6) -0.2394(2) -0.1791(2) 0.0830(8) Uani 1 1 d . . . H2A H 0.4154 -0.2409 -0.2463 0.100 Uiso 1 1 calc R . . C3 C 0.2220(6) -0.1473(2) -0.1343(2) 0.0787(8) Uani 1 1 d . . . H3A H 0.2550 -0.0864 -0.1725 0.094 Uiso 1 1 calc R . . C4 C 0.0782(6) -0.14308(19) -0.0327(2) 0.0690(7) Uani 1 1 d . . . C5 C 0.0285(6) -0.23609(19) 0.0203(2) 0.0756(8) Uani 1 1 d . . . H5A H -0.0696 -0.2352 0.0878 0.091 Uiso 1 1 calc R . . C6 C 0.1191(7) -0.3301(2) -0.0230(2) 0.0822(8) Uani 1 1 d . . . H6A H 0.0858 -0.3916 0.0141 0.099 Uiso 1 1 calc R . . C7 C -0.0241(6) -0.04658(17) 0.0185(2) 0.0773(7) Uani 1 1 d . . . H7A H -0.1341 -0.0522 0.0836 0.093 Uiso 1 1 calc R . . Cl11 Cl -0.371(2) 0.4615(2) 0.1752(7) 0.133(3) Uani 0.50 1 d P . . N1 N -0.360(3) 0.4205(9) 0.1716(11) 0.081(2) Uani 0.50 1 d P . . O1 O -0.308(3) 0.4948(9) 0.1225(7) 0.148(3) Uani 0.50 1 d P . . O2 O -0.4992(14) 0.4115(4) 0.2587(4) 0.1211(19) Uani 0.50 1 d P . . C11 C -0.2604(6) 0.3291(2) 0.1235(2) 0.0767(8) Uani 1 1 d . . . C12 C -0.3157(6) 0.2394(2) 0.1791(2) 0.0830(8) Uani 1 1 d . . . H12A H -0.4154 0.2409 0.2463 0.100 Uiso 1 1 calc R . . C13 C -0.2220(6) 0.1473(2) 0.1343(2) 0.0787(8) Uani 1 1 d . . . H13A H -0.2550 0.0864 0.1725 0.094 Uiso 1 1 calc R . . C14 C -0.0782(6) 0.14308(19) 0.0327(2) 0.0690(7) Uani 1 1 d . . . C15 C -0.0285(6) 0.23609(19) -0.0203(2) 0.0756(8) Uani 1 1 d . . . H15A H 0.0696 0.2352 -0.0878 0.091 Uiso 1 1 calc R . . C16 C -0.1191(7) 0.3301(2) 0.0230(2) 0.0822(8) Uani 1 1 d . . . H16A H -0.0858 0.3916 -0.0141 0.099 Uiso 1 1 calc R . . C17 C 0.0241(6) 0.04658(17) -0.0185(2) 0.0773(7) Uani 1 1 d . . . H17A H 0.1341 0.0522 -0.0836 0.093 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.129(2) 0.112(5) 0.156(5) -0.066(5) 0.004(3) 0.032(3) N11 0.081(4) 0.087(7) 0.074(6) -0.004(5) 0.007(4) 0.005(5) O11 0.208(7) 0.084(4) 0.158(7) -0.006(5) 0.053(5) 0.017(4) O12 0.166(5) 0.092(3) 0.108(4) -0.034(3) 0.035(3) 0.020(3) C1 0.0705(16) 0.0817(19) 0.0777(18) -0.0168(15) 0.0040(13) 0.0040(13) C2 0.0784(17) 0.100(2) 0.0723(18) -0.0062(15) 0.0156(14) -0.0004(14) C3 0.0810(17) 0.0768(17) 0.0792(18) 0.0086(14) 0.0116(13) -0.0019(13) C4 0.0608(14) 0.0753(16) 0.0708(17) -0.0041(13) 0.0032(12) -0.0006(11) C5 0.0811(17) 0.0774(17) 0.0694(16) 0.0016(13) 0.0132(12) 0.0004(13) C6 0.0853(18) 0.0761(18) 0.085(2) 0.0034(14) 0.0059(15) 0.0062(14) C7 0.0723(16) 0.0813(17) 0.0789(17) 0.0065(14) 0.0085(13) -0.0029(14) Cl11 0.129(2) 0.112(5) 0.156(5) -0.066(5) 0.004(3) 0.032(3) N1 0.081(4) 0.087(7) 0.074(6) -0.004(5) 0.007(4) 0.005(5) O1 0.208(7) 0.084(4) 0.158(7) -0.006(5) 0.053(5) 0.017(4) O2 0.166(5) 0.092(3) 0.108(4) -0.034(3) 0.035(3) 0.020(3) C11 0.0705(16) 0.0817(19) 0.0777(18) -0.0168(15) 0.0040(13) 0.0040(13) C12 0.0784(17) 0.100(2) 0.0723(18) -0.0062(15) 0.0156(14) -0.0004(14) C13 0.0810(17) 0.0768(17) 0.0792(18) 0.0086(14) 0.0116(13) -0.0019(13) C14 0.0608(14) 0.0753(16) 0.0708(17) -0.0041(13) 0.0032(12) -0.0006(11) C15 0.0811(17) 0.0774(17) 0.0694(16) 0.0016(13) 0.0132(12) 0.0004(13) C16 0.0853(18) 0.0761(18) 0.085(2) 0.0034(14) 0.0059(15) 0.0062(14) C17 0.0723(16) 0.0813(17) 0.0789(17) 0.0065(14) 0.0085(13) -0.0029(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.536(11) . ? Cl1 O11 0.825(9) . ? Cl1 O12 1.332(8) . ? Cl1 C1 1.888(4) . ? N11 O11 1.16(2) . ? N11 O12 1.231(15) . ? N11 C1 1.388(9) . ? C1 C2 1.371(4) . ? C1 C6 1.376(4) . ? C2 C3 1.371(4) . ? C2 H2A 0.9300 . ? C3 C4 1.395(3) . ? C3 H3A 0.9300 . ? C4 C5 1.388(3) . ? C4 C7 1.465(3) . ? C5 C6 1.383(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.306(4) . ? C7 H7A 0.9300 . ? Cl11 N1 0.536(11) . ? Cl11 O1 0.825(9) . ? Cl11 O2 1.332(8) . ? Cl11 C11 1.888(4) . ? N1 O1 1.16(2) . ? N1 O2 1.231(15) . ? N1 C11 1.388(9) . ? C11 C12 1.371(4) . ? C11 C16 1.376(4) . ? C12 C13 1.371(4) . ? C12 H12A 0.9300 . ? C13 C14 1.395(3) . ? C13 H13A 0.9300 . ? C14 C15 1.388(3) . ? C14 C17 1.465(3) . ? C15 C16 1.383(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 115(3) . . ? N11 Cl1 O12 67(2) . . ? O11 Cl1 O12 175.0(13) . . ? N11 Cl1 C1 18(2) . . ? O11 Cl1 C1 97.4(12) . . ? O12 Cl1 C1 85.3(3) . . ? Cl1 N11 O11 40(2) . . ? Cl1 N11 O12 89(2) . . ? O11 N11 O12 128.8(10) . . ? Cl1 N11 C1 155(3) . . ? O11 N11 C1 115.3(8) . . ? O12 N11 C1 115.8(10) . . ? Cl1 O11 N11 24.7(9) . . ? N11 O12 Cl1 23.7(5) . . ? C2 C1 C6 122.4(3) . . ? C2 C1 N11 117.1(6) . . ? C6 C1 N11 120.5(6) . . ? C2 C1 Cl1 123.9(3) . . ? C6 C1 Cl1 113.7(4) . . ? N11 C1 Cl1 6.8(8) . . ? C1 C2 C3 119.0(2) . . ? C1 C2 H2A 120.5 . . ? C3 C2 H2A 120.5 . . ? C2 C3 C4 121.5(3) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.2(2) . . ? C5 C4 C7 119.5(2) . . ? C3 C4 C7 123.3(2) . . ? C6 C5 C4 122.6(2) . . ? C6 C5 H5A 118.7 . . ? C4 C5 H5A 118.7 . . ? C1 C6 C5 117.3(3) . . ? C1 C6 H6A 121.3 . . ? C5 C6 H6A 121.3 . . ? C17 C7 C4 126.3(3) . . ? C17 C7 H7A 116.8 . . ? C4 C7 H7A 116.8 . . ? N1 Cl11 O1 115(3) . . ? N1 Cl11 O2 67(2) . . ? O1 Cl11 O2 175.0(13) . . ? N1 Cl11 C11 18(2) . . ? O1 Cl11 C11 97.4(12) . . ? O2 Cl11 C11 85.3(3) . . ? Cl11 N1 O1 40(2) . . ? Cl11 N1 O2 89(2) . . ? O1 N1 O2 128.8(10) . . ? Cl11 N1 C11 155(3) . . ? O1 N1 C11 115.3(8) . . ? O2 N1 C11 115.8(10) . . ? Cl11 O1 N1 24.7(9) . . ? N1 O2 Cl11 23.7(5) . . ? C12 C11 C16 122.4(3) . . ? C12 C11 N1 117.1(6) . . ? C16 C11 N1 120.5(6) . . ? C12 C11 Cl11 123.9(3) . . ? C16 C11 Cl11 113.7(4) . . ? N1 C11 Cl11 6.8(8) . . ? C11 C12 C13 119.0(2) . . ? C11 C12 H12A 120.5 . . ? C13 C12 H12A 120.5 . . ? C12 C13 C14 121.5(3) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 117.2(2) . . ? C15 C14 C17 119.5(2) . . ? C13 C14 C17 123.3(2) . . ? C16 C15 C14 122.6(2) . . ? C16 C15 H15A 118.7 . . ? C14 C15 H15A 118.7 . . ? C11 C16 C15 117.3(3) . . ? C11 C16 H16A 121.3 . . ? C15 C16 H16A 121.3 . . ? C7 C17 C14 126.3(3) . . ? C7 C17 H17A 116.8 . . ? C14 C17 H17A 116.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 Cl1 N11 O11 -175.4(16) . . . . ? C1 Cl1 N11 O11 8(8) . . . . ? O11 Cl1 N11 O12 175.4(16) . . . . ? C1 Cl1 N11 O12 -177(7) . . . . ? O11 Cl1 N11 C1 -8(8) . . . . ? O12 Cl1 N11 C1 177(7) . . . . ? O12 Cl1 O11 N11 121(16) . . . . ? C1 Cl1 O11 N11 -2(3) . . . . ? O12 N11 O11 Cl1 -6(2) . . . . ? C1 N11 O11 Cl1 176(4) . . . . ? O11 N11 O12 Cl1 3.8(14) . . . . ? C1 N11 O12 Cl1 -179(3) . . . . ? O11 Cl1 O12 N11 -123(16) . . . . ? C1 Cl1 O12 N11 1(2) . . . . ? Cl1 N11 C1 C2 -174(7) . . . . ? O11 N11 C1 C2 -179.8(10) . . . . ? O12 N11 C1 C2 2.3(13) . . . . ? Cl1 N11 C1 C6 7(7) . . . . ? O11 N11 C1 C6 1.4(15) . . . . ? O12 N11 C1 C6 -176.5(7) . . . . ? O11 N11 C1 Cl1 -5(6) . . . . ? O12 N11 C1 Cl1 177(8) . . . . ? N11 Cl1 C1 C2 6(7) . . . . ? O11 Cl1 C1 C2 179.1(10) . . . . ? O12 Cl1 C1 C2 3.3(6) . . . . ? N11 Cl1 C1 C6 -174(7) . . . . ? O11 Cl1 C1 C6 -0.5(12) . . . . ? O12 Cl1 C1 C6 -176.3(4) . . . . ? O11 Cl1 C1 N11 173(8) . . . . ? O12 Cl1 C1 N11 -3(7) . . . . ? C6 C1 C2 C3 -1.1(4) . . . . ? N11 C1 C2 C3 -179.9(7) . . . . ? Cl1 C1 C2 C3 179.3(3) . . . . ? C1 C2 C3 C4 1.2(4) . . . . ? C2 C3 C4 C5 -1.1(4) . . . . ? C2 C3 C4 C7 179.7(2) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? C7 C4 C5 C6 -180.0(2) . . . . ? C2 C1 C6 C5 0.8(4) . . . . ? N11 C1 C6 C5 179.5(7) . . . . ? Cl1 C1 C6 C5 -179.6(3) . . . . ? C4 C5 C6 C1 -0.7(4) . . . . ? C5 C4 C7 C17 175.9(3) . . . . ? C3 C4 C7 C17 -4.9(5) . . . . ? O2 Cl11 N1 O1 175.4(16) . . . . ? C11 Cl11 N1 O1 -8(8) . . . . ? O1 Cl11 N1 O2 -175.4(16) . . . . ? C11 Cl11 N1 O2 177(7) . . . . ? O1 Cl11 N1 C11 8(8) . . . . ? O2 Cl11 N1 C11 -177(7) . . . . ? O2 Cl11 O1 N1 -121(16) . . . . ? C11 Cl11 O1 N1 2(3) . . . . ? O2 N1 O1 Cl11 6(2) . . . . ? C11 N1 O1 Cl11 -176(4) . . . . ? O1 N1 O2 Cl11 -3.8(14) . . . . ? C11 N1 O2 Cl11 179(3) . . . . ? O1 Cl11 O2 N1 123(16) . . . . ? C11 Cl11 O2 N1 -1(2) . . . . ? Cl11 N1 C11 C12 174(7) . . . . ? O1 N1 C11 C12 179.8(10) . . . . ? O2 N1 C11 C12 -2.3(13) . . . . ? Cl11 N1 C11 C16 -7(7) . . . . ? O1 N1 C11 C16 -1.4(15) . . . . ? O2 N1 C11 C16 176.5(7) . . . . ? O1 N1 C11 Cl11 5(6) . . . . ? O2 N1 C11 Cl11 -177(8) . . . . ? N1 Cl11 C11 C12 -6(7) . . . . ? O1 Cl11 C11 C12 -179.1(10) . . . . ? O2 Cl11 C11 C12 -3.3(6) . . . . ? N1 Cl11 C11 C16 174(7) . . . . ? O1 Cl11 C11 C16 0.5(12) . . . . ? O2 Cl11 C11 C16 176.3(4) . . . . ? O1 Cl11 C11 N1 -173(8) . . . . ? O2 Cl11 C11 N1 3(7) . . . . ? C16 C11 C12 C13 1.1(4) . . . . ? N1 C11 C12 C13 179.9(7) . . . . ? Cl11 C11 C12 C13 -179.3(3) . . . . ? C11 C12 C13 C14 -1.2(4) . . . . ? C12 C13 C14 C15 1.1(4) . . . . ? C12 C13 C14 C17 -179.7(2) . . . . ? C13 C14 C15 C16 -0.8(4) . . . . ? C17 C14 C15 C16 180.0(2) . . . . ? C12 C11 C16 C15 -0.8(4) . . . . ? N1 C11 C16 C15 -179.5(7) . . . . ? Cl11 C11 C16 C15 179.6(3) . . . . ? C14 C15 C16 C11 0.7(4) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.9(3) . . . . ? C13 C14 C17 C7 4.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.864 _diffrn_reflns_theta_full 27.84 _diffrn_measured_fraction_theta_full 0.864 _refine_diff_density_max 0.190 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.045 # start Validation Reply Form _vrf_ABSTM02_CNS-ClTol-small-P21_c ; PROBLEM: The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; _vrf_SYMMG02_CNS-ClTol-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-ClTol-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.86 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; _vrf_PLAT061_CNS-ClTol-small-P21_c ; PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.12 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; # end Validation Reply Form #===END data_CNS-ClTol-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761209' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9182(2) _cell_length_b 12.9555(8) _cell_length_c 12.2381(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.254(3) _cell_angle_gamma 90.00 _cell_volume 620.23(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3482 _cell_measurement_theta_min 3.145 _cell_measurement_theta_max 23.011 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.117740 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3447 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.84 _reflns_number_total 2541 _reflns_number_gt 1202 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0999P)^2^+0.1114P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(3) _refine_ls_number_reflns 2541 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1446 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.2215 _refine_ls_wR_factor_gt 0.1777 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.944 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3671(11) -0.46097(17) -0.1742(4) 0.1196(17) Uani 0.406(3) 1 d P . . N11 N 0.371(3) -0.4164(6) -0.1741(9) 0.090(2) Uani 0.594(3) 1 d P . . O11 O 0.308(2) -0.4979(5) -0.1237(5) 0.136(3) Uani 0.594(3) 1 d P . . O12 O 0.4980(11) -0.4138(3) -0.2581(3) 0.1169(15) Uani 0.594(3) 1 d P . . C1 C 0.2608(6) -0.32939(19) -0.1234(2) 0.0766(7) Uani 1 1 d . . . C2 C 0.3160(5) -0.2387(2) -0.17945(18) 0.0824(7) Uani 1 1 d . . . H2A H 0.4155 -0.2398 -0.2466 0.099 Uiso 1 1 calc R . . C3 C 0.2215(6) -0.14782(18) -0.1341(2) 0.0797(7) Uani 1 1 d . . . H3A H 0.2541 -0.0869 -0.1723 0.096 Uiso 1 1 calc R . . C4 C 0.0783(5) -0.14265(17) -0.03286(17) 0.0679(6) Uani 1 1 d . . . C5 C 0.0285(5) -0.23601(17) 0.02062(19) 0.0757(7) Uani 1 1 d . . . H5A H -0.0696 -0.2352 0.0880 0.091 Uiso 1 1 calc R . . C6 C 0.1196(6) -0.32906(18) -0.0229(2) 0.0813(7) Uani 1 1 d . . . H6A H 0.0868 -0.3904 0.0146 0.098 Uiso 1 1 calc R . . C7 C -0.0240(5) -0.04653(15) 0.01842(19) 0.0753(7) Uani 1 1 d . . . H7A H -0.1339 -0.0522 0.0836 0.090 Uiso 1 1 calc R . . Cl11 Cl -0.3671(11) 0.46097(17) 0.1742(4) 0.1196(17) Uani 0.594(3) 1 d P . . N1 N -0.371(3) 0.4164(6) 0.1741(9) 0.090(2) Uani 0.406(3) 1 d P . . O1 O -0.308(2) 0.4979(5) 0.1237(5) 0.136(3) Uani 0.406(3) 1 d P . . O2 O -0.4980(11) 0.4138(3) 0.2581(3) 0.1169(15) Uani 0.406(3) 1 d P . . C11 C -0.2608(6) 0.32939(19) 0.1234(2) 0.0766(7) Uani 1 1 d . . . C12 C -0.3160(5) 0.2387(2) 0.17945(18) 0.0824(7) Uani 1 1 d . . . H12A H -0.4155 0.2398 0.2466 0.099 Uiso 1 1 calc R . . C13 C -0.2215(6) 0.14782(18) 0.1341(2) 0.0797(7) Uani 1 1 d . . . H13A H -0.2541 0.0869 0.1723 0.096 Uiso 1 1 calc R . . C14 C -0.0783(5) 0.14265(17) 0.03286(17) 0.0679(6) Uani 1 1 d . . . C15 C -0.0285(5) 0.23601(17) -0.02062(19) 0.0757(7) Uani 1 1 d . . . H15A H 0.0696 0.2352 -0.0880 0.091 Uiso 1 1 calc R . . C16 C -0.1196(6) 0.32906(18) 0.0229(2) 0.0813(7) Uani 1 1 d . . . H16A H -0.0868 0.3904 -0.0146 0.098 Uiso 1 1 calc R . . C17 C 0.0240(5) 0.04653(15) -0.01842(19) 0.0753(7) Uani 1 1 d . . . H17A H 0.1339 0.0522 -0.0836 0.090 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1229(19) 0.095(3) 0.141(3) -0.047(3) 0.011(2) 0.018(2) N11 0.098(4) 0.070(5) 0.100(6) 0.005(5) -0.011(4) -0.011(5) O11 0.188(5) 0.077(3) 0.147(5) 0.011(3) 0.052(4) 0.012(3) O12 0.166(4) 0.087(3) 0.101(3) -0.030(2) 0.036(3) 0.019(2) C1 0.0699(15) 0.0801(17) 0.0797(16) -0.0159(13) 0.0033(12) 0.0034(12) C2 0.0766(16) 0.100(2) 0.0722(16) -0.0042(13) 0.0161(12) -0.0003(13) C3 0.0793(15) 0.0793(16) 0.0809(17) 0.0095(13) 0.0099(12) -0.0031(12) C4 0.0609(12) 0.0770(15) 0.0658(14) -0.0056(11) 0.0045(10) 0.0004(10) C5 0.0802(15) 0.0791(16) 0.0690(14) 0.0047(12) 0.0140(11) -0.0019(12) C6 0.0862(16) 0.0734(16) 0.0845(18) 0.0012(13) 0.0072(13) 0.0046(12) C7 0.0721(14) 0.0773(15) 0.0771(15) 0.0062(12) 0.0085(11) -0.0029(12) Cl11 0.1229(19) 0.095(3) 0.141(3) -0.047(3) 0.011(2) 0.018(2) N1 0.098(4) 0.070(5) 0.100(6) 0.005(5) -0.011(4) -0.011(5) O1 0.188(5) 0.077(3) 0.147(5) 0.011(3) 0.052(4) 0.012(3) O2 0.166(4) 0.087(3) 0.101(3) -0.030(2) 0.036(3) 0.019(2) C11 0.0699(15) 0.0801(17) 0.0797(16) -0.0159(13) 0.0033(12) 0.0034(12) C12 0.0766(16) 0.100(2) 0.0722(16) -0.0042(13) 0.0161(12) -0.0003(13) C13 0.0793(15) 0.0793(16) 0.0809(17) 0.0095(13) 0.0099(12) -0.0031(12) C14 0.0609(12) 0.0770(15) 0.0658(14) -0.0056(11) 0.0045(10) 0.0004(10) C15 0.0802(15) 0.0791(16) 0.0690(14) 0.0047(12) 0.0140(11) -0.0019(12) C16 0.0862(16) 0.0734(16) 0.0845(18) 0.0012(13) 0.0072(13) 0.0046(12) C17 0.0721(14) 0.0773(15) 0.0771(15) 0.0062(12) 0.0085(11) -0.0029(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.578(8) . ? Cl1 O11 0.825(5) . ? Cl1 O12 1.324(6) . ? Cl1 C1 1.869(3) . ? N11 O11 1.255(13) . ? N11 O12 1.168(12) . ? N11 C1 1.368(8) . ? C1 C2 1.384(3) . ? C1 C6 1.377(3) . ? C2 C3 1.361(3) . ? C2 H2A 0.9300 . ? C3 C4 1.391(3) . ? C3 H3A 0.9300 . ? C4 C5 1.394(3) . ? C4 C7 1.461(3) . ? C5 C6 1.373(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.305(4) . ? C7 H7A 0.9300 . ? Cl11 N1 0.578(8) . ? Cl11 O1 0.825(5) . ? Cl11 O2 1.324(6) . ? Cl11 C11 1.869(3) . ? N1 O1 1.255(13) . ? N1 O2 1.168(12) . ? N1 C11 1.368(8) . ? C11 C12 1.384(3) . ? C11 C16 1.377(3) . ? C12 C13 1.361(3) . ? C12 H12A 0.9300 . ? C13 C14 1.391(3) . ? C13 H13A 0.9300 . ? C14 C15 1.394(3) . ? C14 C17 1.461(3) . ? C15 C16 1.373(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 126.0(19) . . ? N11 Cl1 O12 61.8(15) . . ? O11 Cl1 O12 170.7(7) . . ? N11 Cl1 C1 25.1(14) . . ? O11 Cl1 C1 101.7(7) . . ? O12 Cl1 C1 86.6(2) . . ? Cl1 N11 O11 32.1(13) . . ? Cl1 N11 O12 92.3(15) . . ? O11 N11 O12 124.3(7) . . ? Cl1 N11 C1 144.6(19) . . ? O11 N11 C1 113.2(9) . . ? O12 N11 C1 122.4(8) . . ? Cl1 O11 N11 21.9(7) . . ? N11 O12 Cl1 25.8(4) . . ? C2 C1 C6 121.5(2) . . ? C2 C1 N11 114.4(5) . . ? C6 C1 N11 124.1(5) . . ? C2 C1 Cl1 124.5(2) . . ? C6 C1 Cl1 114.1(2) . . ? N11 C1 Cl1 10.3(6) . . ? C1 C2 C3 118.6(2) . . ? C1 C2 H2A 120.7 . . ? C3 C2 H2A 120.7 . . ? C2 C3 C4 122.5(2) . . ? C2 C3 H3A 118.7 . . ? C4 C3 H3A 118.7 . . ? C5 C4 C3 116.8(2) . . ? C5 C4 C7 119.3(2) . . ? C3 C4 C7 123.9(2) . . ? C6 C5 C4 122.2(2) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C1 C6 C5 118.4(2) . . ? C1 C6 H6A 120.8 . . ? C5 C6 H6A 120.8 . . ? C17 C7 C4 126.2(3) . . ? C17 C7 H7A 116.9 . . ? C4 C7 H7A 116.9 . . ? N1 Cl11 O1 126.0(19) . . ? N1 Cl11 O2 61.8(15) . . ? O1 Cl11 O2 170.7(7) . . ? N1 Cl11 C11 25.1(14) . . ? O1 Cl11 C11 101.7(7) . . ? O2 Cl11 C11 86.6(2) . . ? Cl11 N1 O1 32.1(13) . . ? Cl11 N1 O2 92.3(15) . . ? O1 N1 O2 124.3(7) . . ? Cl11 N1 C11 144.6(19) . . ? O1 N1 C11 113.2(9) . . ? O2 N1 C11 122.4(8) . . ? Cl11 O1 N1 21.9(7) . . ? N1 O2 Cl11 25.8(4) . . ? C12 C11 C16 121.5(2) . . ? C12 C11 N1 114.4(5) . . ? C16 C11 N1 124.1(5) . . ? C12 C11 Cl11 124.5(2) . . ? C16 C11 Cl11 114.1(2) . . ? N1 C11 Cl11 10.3(6) . . ? C11 C12 C13 118.6(2) . . ? C11 C12 H12A 120.7 . . ? C13 C12 H12A 120.7 . . ? C12 C13 C14 122.5(2) . . ? C12 C13 H13A 118.7 . . ? C14 C13 H13A 118.7 . . ? C15 C14 C13 116.8(2) . . ? C15 C14 C17 119.3(2) . . ? C13 C14 C17 123.9(2) . . ? C16 C15 C14 122.2(2) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C11 C16 C15 118.4(2) . . ? C11 C16 H16A 120.8 . . ? C15 C16 H16A 120.8 . . ? C7 C17 C14 126.2(3) . . ? C7 C17 H17A 116.9 . . ? C14 C17 H17A 116.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 Cl1 N11 O11 -174.2(12) . . . . ? C1 Cl1 N11 O11 16(4) . . . . ? O11 Cl1 N11 O12 174.2(11) . . . . ? C1 Cl1 N11 O12 -170(4) . . . . ? O11 Cl1 N11 C1 -16(4) . . . . ? O12 Cl1 N11 C1 170(4) . . . . ? O12 Cl1 O11 N11 146(7) . . . . ? C1 Cl1 O11 N11 -6.8(19) . . . . ? O12 N11 O11 Cl1 -7.1(14) . . . . ? C1 N11 O11 Cl1 170(3) . . . . ? O11 N11 O12 Cl1 3.8(8) . . . . ? C1 N11 O12 Cl1 -173(2) . . . . ? O11 Cl1 O12 N11 -149(6) . . . . ? C1 Cl1 O12 N11 4.3(15) . . . . ? Cl1 N11 C1 C2 -169(3) . . . . ? O11 N11 C1 C2 -177.7(8) . . . . ? O12 N11 C1 C2 -0.6(12) . . . . ? Cl1 N11 C1 C6 14(4) . . . . ? O11 N11 C1 C6 5.0(13) . . . . ? O12 N11 C1 C6 -177.8(7) . . . . ? O11 N11 C1 Cl1 -9(3) . . . . ? O12 N11 C1 Cl1 168(4) . . . . ? N11 Cl1 C1 C2 13(3) . . . . ? O11 Cl1 C1 C2 179.5(7) . . . . ? O12 Cl1 C1 C2 3.7(4) . . . . ? N11 Cl1 C1 C6 -167(3) . . . . ? O11 Cl1 C1 C6 -0.3(8) . . . . ? O12 Cl1 C1 C6 -176.1(3) . . . . ? O11 Cl1 C1 N11 167(4) . . . . ? O12 Cl1 C1 N11 -9(3) . . . . ? C6 C1 C2 C3 -1.2(4) . . . . ? N11 C1 C2 C3 -178.6(5) . . . . ? Cl1 C1 C2 C3 178.9(3) . . . . ? C1 C2 C3 C4 1.3(4) . . . . ? C2 C3 C4 C5 -1.1(3) . . . . ? C2 C3 C4 C7 179.6(2) . . . . ? C3 C4 C5 C6 0.9(3) . . . . ? C7 C4 C5 C6 -179.8(2) . . . . ? C2 C1 C6 C5 1.0(4) . . . . ? N11 C1 C6 C5 178.1(6) . . . . ? Cl1 C1 C6 C5 -179.2(2) . . . . ? C4 C5 C6 C1 -0.8(3) . . . . ? C5 C4 C7 C17 175.8(3) . . . . ? C3 C4 C7 C17 -5.0(4) . . . . ? O2 Cl11 N1 O1 174.2(12) . . . . ? C11 Cl11 N1 O1 -16(4) . . . . ? O1 Cl11 N1 O2 -174.2(11) . . . . ? C11 Cl11 N1 O2 170(4) . . . . ? O1 Cl11 N1 C11 16(4) . . . . ? O2 Cl11 N1 C11 -170(4) . . . . ? O2 Cl11 O1 N1 -146(7) . . . . ? C11 Cl11 O1 N1 6.8(19) . . . . ? O2 N1 O1 Cl11 7.1(14) . . . . ? C11 N1 O1 Cl11 -170(3) . . . . ? O1 N1 O2 Cl11 -3.8(8) . . . . ? C11 N1 O2 Cl11 173(2) . . . . ? O1 Cl11 O2 N1 149(6) . . . . ? C11 Cl11 O2 N1 -4.3(15) . . . . ? Cl11 N1 C11 C12 169(3) . . . . ? O1 N1 C11 C12 177.7(8) . . . . ? O2 N1 C11 C12 0.6(12) . . . . ? Cl11 N1 C11 C16 -14(4) . . . . ? O1 N1 C11 C16 -5.0(13) . . . . ? O2 N1 C11 C16 177.8(7) . . . . ? O1 N1 C11 Cl11 9(3) . . . . ? O2 N1 C11 Cl11 -168(4) . . . . ? N1 Cl11 C11 C12 -13(3) . . . . ? O1 Cl11 C11 C12 -179.5(7) . . . . ? O2 Cl11 C11 C12 -3.7(4) . . . . ? N1 Cl11 C11 C16 167(3) . . . . ? O1 Cl11 C11 C16 0.3(8) . . . . ? O2 Cl11 C11 C16 176.1(3) . . . . ? O1 Cl11 C11 N1 -167(4) . . . . ? O2 Cl11 C11 N1 9(3) . . . . ? C16 C11 C12 C13 1.2(4) . . . . ? N1 C11 C12 C13 178.6(5) . . . . ? Cl11 C11 C12 C13 -178.9(3) . . . . ? C11 C12 C13 C14 -1.3(4) . . . . ? C12 C13 C14 C15 1.1(3) . . . . ? C12 C13 C14 C17 -179.6(2) . . . . ? C13 C14 C15 C16 -0.9(3) . . . . ? C17 C14 C15 C16 179.8(2) . . . . ? C12 C11 C16 C15 -1.0(4) . . . . ? N1 C11 C16 C15 -178.1(6) . . . . ? Cl11 C11 C16 C15 179.2(2) . . . . ? C14 C15 C16 C11 0.8(3) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.8(3) . . . . ? C13 C14 C17 C7 5.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 27.84 _diffrn_measured_fraction_theta_full 0.900 _refine_diff_density_max 0.195 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.045 # start Validation Reply Form _vrf_ABSTM02_CNS-ClTol-small-P21 ; PROBLEM: The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; _vrf_SYMMG02_CNS-ClTol-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-ClTol-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.90 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; _vrf_PLAT061_CNS-ClTol-small-P21 ; PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.12 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; # end Validation Reply Form #===END data_CNS-TolI-small-P21_c _database_code_depnum_ccdc_archive 'CCDC 761210' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9236(3) _cell_length_b 12.9740(8) _cell_length_c 12.2406(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.175(3) _cell_angle_gamma 90.00 _cell_volume 622.15(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3480 _cell_measurement_theta_min 3.1405 _cell_measurement_theta_max 22.987 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.753678 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3452 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.82 _reflns_number_total 2482 _reflns_number_gt 1215 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.1171P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2482 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1271 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1438 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.168 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3683(13) -0.46092(14) -0.1748(5) 0.1123(17) Uani 0.50 1 d P . . N11 N 0.369(3) -0.4160(6) -0.1728(11) 0.082(2) Uani 0.50 1 d P . . O11 O 0.310(2) -0.4971(5) -0.1233(5) 0.132(3) Uani 0.50 1 d P . . O12 O 0.5000(10) -0.4128(3) -0.2573(3) 0.1125(13) Uani 0.50 1 d P . . C1 C 0.2601(5) -0.32906(17) -0.12309(18) 0.0717(6) Uani 1 1 d . . . C2 C 0.3153(5) -0.23917(19) -0.17883(16) 0.0819(6) Uani 1 1 d . . . H2A H 0.4145 -0.2408 -0.2461 0.098 Uiso 1 1 calc R . . C3 C 0.2228(5) -0.14756(16) -0.13438(17) 0.0749(6) Uani 1 1 d . . . H3A H 0.2568 -0.0868 -0.1726 0.090 Uiso 1 1 calc R . . C4 C 0.0780(5) -0.14318(15) -0.03270(16) 0.0654(5) Uani 1 1 d . . . C5 C 0.0284(5) -0.23586(15) 0.02065(16) 0.0727(6) Uani 1 1 d . . . H5A H -0.0698 -0.2348 0.0881 0.087 Uiso 1 1 calc R . . C6 C 0.1189(5) -0.32937(15) -0.02243(17) 0.0767(6) Uani 1 1 d . . . H6A H 0.0859 -0.3906 0.0151 0.092 Uiso 1 1 calc R . . C7 C -0.0233(5) -0.04638(13) 0.01827(17) 0.0736(6) Uani 1 1 d . . . H7A H -0.1324 -0.0519 0.0836 0.088 Uiso 1 1 calc R . . Cl11 Cl -0.3683(13) 0.46092(14) 0.1748(5) 0.1123(17) Uani 0.50 1 d P . . N1 N -0.369(3) 0.4160(6) 0.1728(11) 0.082(2) Uani 0.50 1 d P . . O1 O -0.310(2) 0.4971(5) 0.1233(5) 0.132(3) Uani 0.50 1 d P . . O2 O -0.5000(10) 0.4128(3) 0.2573(3) 0.1125(13) Uani 0.50 1 d P . . C11 C -0.2601(5) 0.32906(17) 0.12309(18) 0.0717(6) Uani 1 1 d . . . C12 C -0.3153(5) 0.23917(19) 0.17883(16) 0.0819(6) Uani 1 1 d . . . H12A H -0.4145 0.2408 0.2461 0.098 Uiso 1 1 calc R . . C13 C -0.2228(5) 0.14756(16) 0.13438(17) 0.0749(6) Uani 1 1 d . . . H13A H -0.2568 0.0868 0.1726 0.090 Uiso 1 1 calc R . . C14 C -0.0780(5) 0.14318(15) 0.03270(16) 0.0654(5) Uani 1 1 d . . . C15 C -0.0284(5) 0.23586(15) -0.02065(16) 0.0727(6) Uani 1 1 d . . . H15A H 0.0698 0.2348 -0.0881 0.087 Uiso 1 1 calc R . . C16 C -0.1189(5) 0.32937(15) 0.02243(17) 0.0767(6) Uani 1 1 d . . . H16A H -0.0859 0.3906 -0.0151 0.092 Uiso 1 1 calc R . . C17 C 0.0233(5) 0.04638(13) -0.01827(17) 0.0736(6) Uani 1 1 d . . . H17A H 0.1324 0.0519 -0.0836 0.088 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1139(18) 0.092(4) 0.132(3) -0.046(3) 0.0085(19) 0.018(3) N11 0.081(4) 0.066(5) 0.100(6) 0.005(5) -0.001(4) -0.003(5) O11 0.174(5) 0.080(3) 0.147(5) 0.007(3) 0.047(4) 0.012(3) O12 0.152(3) 0.094(2) 0.095(3) -0.028(2) 0.034(2) 0.018(2) C1 0.0598(13) 0.0792(15) 0.0756(15) -0.0151(12) -0.0008(11) 0.0060(12) C2 0.0710(14) 0.1083(17) 0.0670(14) -0.0037(13) 0.0099(11) -0.0002(13) C3 0.0693(14) 0.0834(14) 0.0727(15) 0.0082(12) 0.0094(11) -0.0016(12) C4 0.0521(11) 0.0776(13) 0.0660(14) -0.0062(11) 0.0001(10) -0.0018(10) C5 0.0692(13) 0.0853(15) 0.0644(13) 0.0014(12) 0.0105(10) -0.0026(12) C6 0.0739(14) 0.0773(15) 0.0790(16) 0.0019(12) 0.0051(12) 0.0041(12) C7 0.0647(13) 0.0831(14) 0.0731(14) 0.0054(12) 0.0061(10) -0.0022(12) Cl11 0.1139(18) 0.092(4) 0.132(3) -0.046(3) 0.0085(19) 0.018(3) N1 0.081(4) 0.066(5) 0.100(6) 0.005(5) -0.001(4) -0.003(5) O1 0.174(5) 0.080(3) 0.147(5) 0.007(3) 0.047(4) 0.012(3) O2 0.152(3) 0.094(2) 0.095(3) -0.028(2) 0.034(2) 0.018(2) C11 0.0598(13) 0.0792(15) 0.0756(15) -0.0151(12) -0.0008(11) 0.0060(12) C12 0.0710(14) 0.1083(17) 0.0670(14) -0.0037(13) 0.0099(11) -0.0002(13) C13 0.0693(14) 0.0834(14) 0.0727(15) 0.0082(12) 0.0094(11) -0.0016(12) C14 0.0521(11) 0.0776(13) 0.0660(14) -0.0062(11) 0.0001(10) -0.0018(10) C15 0.0692(13) 0.0853(15) 0.0644(13) 0.0014(12) 0.0105(10) -0.0026(12) C16 0.0739(14) 0.0773(15) 0.0790(16) 0.0019(12) 0.0051(12) 0.0041(12) C17 0.0647(13) 0.0831(14) 0.0731(14) 0.0054(12) 0.0061(10) -0.0022(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.583(7) . ? Cl1 O11 0.828(5) . ? Cl1 O12 1.317(6) . ? Cl1 C1 1.881(3) . ? N11 O12 1.180(14) . ? N11 O11 1.243(15) . ? N11 C1 1.362(7) . ? C1 C2 1.374(3) . ? C1 C6 1.379(3) . ? C2 C3 1.365(3) . ? C2 H2A 0.9300 . ? C3 C4 1.398(3) . ? C3 H3A 0.9300 . ? C4 C5 1.387(2) . ? C4 C7 1.467(2) . ? C5 C6 1.377(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.300(3) . ? C7 H7A 0.9300 . ? Cl11 N1 0.583(7) . ? Cl11 O1 0.828(5) . ? Cl11 O2 1.317(6) . ? Cl11 C11 1.881(3) . ? N1 O2 1.180(14) . ? N1 O1 1.243(15) . ? N1 C11 1.362(7) . ? C11 C12 1.374(3) . ? C11 C16 1.379(3) . ? C12 C13 1.365(3) . ? C12 H12A 0.9300 . ? C13 C14 1.398(3) . ? C13 H13A 0.9300 . ? C14 C15 1.387(2) . ? C14 C17 1.467(2) . ? C15 C16 1.377(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 122(2) . . ? N11 Cl1 O12 63.7(17) . . ? O11 Cl1 O12 171.3(8) . . ? N11 Cl1 C1 22.9(16) . . ? O11 Cl1 C1 100.6(8) . . ? O12 Cl1 C1 86.1(2) . . ? Cl1 N11 O12 90.1(17) . . ? Cl1 N11 O11 34.2(15) . . ? O12 N11 O11 124.0(7) . . ? Cl1 N11 C1 148(2) . . ? O12 N11 C1 121.7(9) . . ? O11 N11 C1 114.3(9) . . ? Cl1 O11 N11 23.3(7) . . ? N11 O12 Cl1 26.3(3) . . ? N11 C1 C2 114.8(6) . . ? N11 C1 C6 123.3(6) . . ? C2 C1 C6 121.9(2) . . ? N11 C1 Cl1 9.6(7) . . ? C2 C1 Cl1 124.1(2) . . ? C6 C1 Cl1 114.0(3) . . ? C3 C2 C1 119.2(2) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.4(2) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.3(2) . . ? C5 C4 C7 119.56(18) . . ? C3 C4 C7 123.1(2) . . ? C6 C5 C4 122.5(2) . . ? C6 C5 H5A 118.7 . . ? C4 C5 H5A 118.7 . . ? C5 C6 C1 117.7(2) . . ? C5 C6 H6A 121.2 . . ? C1 C6 H6A 121.2 . . ? C17 C7 C4 126.8(3) . . ? C17 C7 H7A 116.6 . . ? C4 C7 H7A 116.6 . . ? N1 Cl11 O1 122(2) . . ? N1 Cl11 O2 63.7(17) . . ? O1 Cl11 O2 171.3(8) . . ? N1 Cl11 C11 22.9(16) . . ? O1 Cl11 C11 100.6(8) . . ? O2 Cl11 C11 86.1(2) . . ? Cl11 N1 O2 90.1(17) . . ? Cl11 N1 O1 34.2(15) . . ? O2 N1 O1 124.0(7) . . ? Cl11 N1 C11 148(2) . . ? O2 N1 C11 121.7(9) . . ? O1 N1 C11 114.3(9) . . ? Cl11 O1 N1 23.3(7) . . ? N1 O2 Cl11 26.3(3) . . ? N1 C11 C12 114.8(6) . . ? N1 C11 C16 123.3(6) . . ? C12 C11 C16 121.9(2) . . ? N1 C11 Cl11 9.6(7) . . ? C12 C11 Cl11 124.1(2) . . ? C16 C11 Cl11 114.0(3) . . ? C13 C12 C11 119.2(2) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 121.4(2) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 117.3(2) . . ? C15 C14 C17 119.56(18) . . ? C13 C14 C17 123.1(2) . . ? C16 C15 C14 122.5(2) . . ? C16 C15 H15A 118.7 . . ? C14 C15 H15A 118.7 . . ? C15 C16 C11 117.7(2) . . ? C15 C16 H16A 121.2 . . ? C11 C16 H16A 121.2 . . ? C7 C17 C14 126.8(3) . . ? C7 C17 H17A 116.6 . . ? C14 C17 H17A 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 173.0(11) . . . . ? C1 Cl1 N11 O12 -169(4) . . . . ? O12 Cl1 N11 O11 -173.0(11) . . . . ? C1 Cl1 N11 O11 18(5) . . . . ? O11 Cl1 N11 C1 -18(5) . . . . ? O12 Cl1 N11 C1 169(4) . . . . ? O12 Cl1 O11 N11 133(7) . . . . ? C1 Cl1 O11 N11 -7.0(19) . . . . ? O12 N11 O11 Cl1 -8.5(14) . . . . ? C1 N11 O11 Cl1 169(3) . . . . ? O11 N11 O12 Cl1 4.8(8) . . . . ? C1 N11 O12 Cl1 -173(3) . . . . ? O11 Cl1 O12 N11 -137(6) . . . . ? C1 Cl1 O12 N11 4.3(16) . . . . ? Cl1 N11 C1 C2 -167(4) . . . . ? O12 N11 C1 C2 -0.2(13) . . . . ? O11 N11 C1 C2 -178.2(9) . . . . ? Cl1 N11 C1 C6 16(4) . . . . ? O12 N11 C1 C6 -177.3(7) . . . . ? O11 N11 C1 C6 4.6(14) . . . . ? O12 N11 C1 Cl1 167(5) . . . . ? O11 N11 C1 Cl1 -11(3) . . . . ? O11 Cl1 C1 N11 165(4) . . . . ? O12 Cl1 C1 N11 -10(4) . . . . ? N11 Cl1 C1 C2 14(4) . . . . ? O11 Cl1 C1 C2 178.7(7) . . . . ? O12 Cl1 C1 C2 4.2(4) . . . . ? N11 Cl1 C1 C6 -166(4) . . . . ? O11 Cl1 C1 C6 -1.2(8) . . . . ? O12 Cl1 C1 C6 -175.6(3) . . . . ? N11 C1 C2 C3 -178.3(6) . . . . ? C6 C1 C2 C3 -1.1(3) . . . . ? Cl1 C1 C2 C3 179.1(3) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C2 C3 C4 C7 179.7(2) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C7 C4 C5 C6 -179.75(18) . . . . ? C4 C5 C6 C1 -0.8(3) . . . . ? N11 C1 C6 C5 178.0(6) . . . . ? C2 C1 C6 C5 1.0(3) . . . . ? Cl1 C1 C6 C5 -179.2(2) . . . . ? C5 C4 C7 C17 175.9(3) . . . . ? C3 C4 C7 C17 -4.5(4) . . . . ? O1 Cl11 N1 O2 -173.0(11) . . . . ? C11 Cl11 N1 O2 169(4) . . . . ? O2 Cl11 N1 O1 173.0(11) . . . . ? C11 Cl11 N1 O1 -18(5) . . . . ? O1 Cl11 N1 C11 18(5) . . . . ? O2 Cl11 N1 C11 -169(4) . . . . ? O2 Cl11 O1 N1 -133(7) . . . . ? C11 Cl11 O1 N1 7.0(19) . . . . ? O2 N1 O1 Cl11 8.5(14) . . . . ? C11 N1 O1 Cl11 -169(3) . . . . ? O1 N1 O2 Cl11 -4.8(8) . . . . ? C11 N1 O2 Cl11 173(3) . . . . ? O1 Cl11 O2 N1 137(6) . . . . ? C11 Cl11 O2 N1 -4.3(16) . . . . ? Cl11 N1 C11 C12 167(4) . . . . ? O2 N1 C11 C12 0.2(13) . . . . ? O1 N1 C11 C12 178.2(9) . . . . ? Cl11 N1 C11 C16 -16(4) . . . . ? O2 N1 C11 C16 177.3(7) . . . . ? O1 N1 C11 C16 -4.6(14) . . . . ? O2 N1 C11 Cl11 -167(5) . . . . ? O1 N1 C11 Cl11 11(3) . . . . ? O1 Cl11 C11 N1 -165(4) . . . . ? O2 Cl11 C11 N1 10(4) . . . . ? N1 Cl11 C11 C12 -14(4) . . . . ? O1 Cl11 C11 C12 -178.7(7) . . . . ? O2 Cl11 C11 C12 -4.2(4) . . . . ? N1 Cl11 C11 C16 166(4) . . . . ? O1 Cl11 C11 C16 1.2(8) . . . . ? O2 Cl11 C11 C16 175.6(3) . . . . ? N1 C11 C12 C13 178.3(6) . . . . ? C16 C11 C12 C13 1.1(3) . . . . ? Cl11 C11 C12 C13 -179.1(3) . . . . ? C11 C12 C13 C14 -1.0(3) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? C12 C13 C14 C17 -179.7(2) . . . . ? C13 C14 C15 C16 -0.7(3) . . . . ? C17 C14 C15 C16 179.75(18) . . . . ? C14 C15 C16 C11 0.8(3) . . . . ? N1 C11 C16 C15 -178.0(6) . . . . ? C12 C11 C16 C15 -1.0(3) . . . . ? Cl11 C11 C16 C15 179.2(2) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.9(3) . . . . ? C13 C14 C17 C7 4.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.863 _diffrn_reflns_theta_full 27.82 _diffrn_measured_fraction_theta_full 0.863 _refine_diff_density_max 0.109 _refine_diff_density_min -0.101 _refine_diff_density_rms 0.025 # start Validation Reply Form _vrf_SYMMG02_CNS-TolI-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-TolI-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.86 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; # end Validation Reply Form #===END data_CNS-TolI-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761211' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9236(3) _cell_length_b 12.9740(8) _cell_length_c 12.2406(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.175(3) _cell_angle_gamma 90.00 _cell_volume 622.15(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3480 _cell_measurement_theta_min 3.1405 _cell_measurement_theta_max 22.987 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.753678 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3452 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.82 _reflns_number_total 2482 _reflns_number_gt 1215 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.1171P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(2) _refine_ls_number_reflns 2482 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1202 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3677(9) -0.46073(13) -0.1750(3) 0.1103(12) Uani 0.408(2) 1 d P . . N11 N 0.373(2) -0.4153(4) -0.1729(8) 0.0846(18) Uani 0.592(2) 1 d P . . O11 O 0.3094(16) -0.4972(4) -0.1239(4) 0.128(2) Uani 0.592(2) 1 d P . . O12 O 0.5003(9) -0.4133(2) -0.2576(3) 0.1116(11) Uani 0.592(2) 1 d P . . C1 C 0.2606(4) -0.32920(15) -0.12317(16) 0.0723(5) Uani 1 1 d . . . C2 C 0.3154(5) -0.23907(17) -0.17913(15) 0.0808(6) Uani 1 1 d . . . H2A H 0.4142 -0.2405 -0.2465 0.097 Uiso 1 1 calc R . . C3 C 0.2226(4) -0.14770(15) -0.13427(15) 0.0758(5) Uani 1 1 d . . . H3A H 0.2566 -0.0869 -0.1724 0.091 Uiso 1 1 calc R . . C4 C 0.0781(4) -0.14291(14) -0.03286(14) 0.0647(5) Uani 1 1 d . . . C5 C 0.0286(4) -0.23589(14) 0.02063(15) 0.0729(5) Uani 1 1 d . . . H5A H -0.0694 -0.2349 0.0881 0.088 Uiso 1 1 calc R . . C6 C 0.1192(4) -0.32911(14) -0.02243(15) 0.0765(6) Uani 1 1 d . . . H6A H 0.0863 -0.3903 0.0152 0.092 Uiso 1 1 calc R . . C7 C -0.0232(4) -0.04640(11) 0.01817(15) 0.0729(5) Uani 1 1 d . . . H7A H -0.1324 -0.0521 0.0834 0.087 Uiso 1 1 calc R . . Cl11 Cl -0.3677(9) 0.46073(13) 0.1750(3) 0.1103(12) Uani 0.592(2) 1 d P . . N1 N -0.373(2) 0.4153(4) 0.1729(8) 0.0846(18) Uani 0.408(2) 1 d P . . O1 O -0.3094(16) 0.4972(4) 0.1239(4) 0.128(2) Uani 0.408(2) 1 d P . . O2 O -0.5003(9) 0.4133(2) 0.2576(3) 0.1116(11) Uani 0.408(2) 1 d P . . C11 C -0.2606(4) 0.32920(15) 0.12317(16) 0.0723(5) Uani 1 1 d . . . C12 C -0.3154(5) 0.23907(17) 0.17913(15) 0.0808(6) Uani 1 1 d . . . H12A H -0.4142 0.2405 0.2465 0.097 Uiso 1 1 calc R . . C13 C -0.2226(4) 0.14770(15) 0.13427(15) 0.0758(5) Uani 1 1 d . . . H13A H -0.2566 0.0869 0.1724 0.091 Uiso 1 1 calc R . . C14 C -0.0781(4) 0.14291(14) 0.03286(14) 0.0647(5) Uani 1 1 d . . . C15 C -0.0286(4) 0.23589(14) -0.02063(15) 0.0729(5) Uani 1 1 d . . . H15A H 0.0694 0.2349 -0.0881 0.088 Uiso 1 1 calc R . . C16 C -0.1192(4) 0.32911(14) 0.02243(15) 0.0765(6) Uani 1 1 d . . . H16A H -0.0863 0.3903 -0.0152 0.092 Uiso 1 1 calc R . . C17 C 0.0232(4) 0.04640(11) -0.01817(15) 0.0729(5) Uani 1 1 d . . . H17A H 0.1324 0.0521 -0.0834 0.087 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1113(15) 0.090(2) 0.130(2) -0.044(2) 0.0103(15) 0.014(2) N11 0.085(3) 0.063(4) 0.105(5) 0.002(4) -0.008(3) -0.006(4) O11 0.167(4) 0.077(3) 0.144(4) 0.010(2) 0.049(3) 0.010(2) O12 0.152(3) 0.092(2) 0.094(2) -0.0257(19) 0.037(2) 0.016(2) C1 0.0585(12) 0.0816(14) 0.0762(13) -0.0150(11) -0.0013(10) 0.0059(10) C2 0.0710(13) 0.1058(15) 0.0662(13) -0.0033(12) 0.0110(10) -0.0004(12) C3 0.0687(12) 0.0852(13) 0.0740(13) 0.0092(11) 0.0076(10) -0.0028(10) C4 0.0521(10) 0.0779(12) 0.0638(12) -0.0062(10) 0.0011(9) -0.0014(9) C5 0.0687(12) 0.0861(13) 0.0648(11) 0.0019(11) 0.0106(9) -0.0019(11) C6 0.0740(13) 0.0777(13) 0.0781(14) 0.0021(11) 0.0057(11) 0.0030(10) C7 0.0646(11) 0.0818(13) 0.0725(12) 0.0051(10) 0.0056(9) -0.0021(11) Cl11 0.1113(15) 0.090(2) 0.130(2) -0.044(2) 0.0103(15) 0.014(2) N1 0.085(3) 0.063(4) 0.105(5) 0.002(4) -0.008(3) -0.006(4) O1 0.167(4) 0.077(3) 0.144(4) 0.010(2) 0.049(3) 0.010(2) O2 0.152(3) 0.092(2) 0.094(2) -0.0257(19) 0.037(2) 0.016(2) C11 0.0585(12) 0.0816(14) 0.0762(13) -0.0150(11) -0.0013(10) 0.0059(10) C12 0.0710(13) 0.1058(15) 0.0662(13) -0.0033(12) 0.0110(10) -0.0004(12) C13 0.0687(12) 0.0852(13) 0.0740(13) 0.0092(11) 0.0076(10) -0.0028(10) C14 0.0521(10) 0.0779(12) 0.0638(12) -0.0062(10) 0.0011(9) -0.0014(9) C15 0.0687(12) 0.0861(13) 0.0648(11) 0.0019(11) 0.0106(9) -0.0019(11) C16 0.0740(13) 0.0777(13) 0.0781(14) 0.0021(11) 0.0057(11) 0.0030(10) C17 0.0646(11) 0.0818(13) 0.0725(12) 0.0051(10) 0.0056(9) -0.0021(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.591(6) . ? Cl1 O11 0.827(4) . ? Cl1 O12 1.315(5) . ? Cl1 C1 1.877(2) . ? N11 O12 1.175(10) . ? N11 O11 1.254(11) . ? N11 C1 1.357(6) . ? C1 C2 1.378(2) . ? C1 C6 1.380(2) . ? C2 C3 1.364(2) . ? C2 H2A 0.9300 . ? C3 C4 1.394(2) . ? C3 H3A 0.9300 . ? C4 C5 1.391(2) . ? C4 C7 1.464(2) . ? C5 C6 1.374(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.300(3) . ? C7 H7A 0.9300 . ? Cl11 N1 0.591(6) . ? Cl11 O1 0.827(4) . ? Cl11 O2 1.315(5) . ? Cl11 C11 1.877(2) . ? N1 O2 1.175(10) . ? N1 O1 1.254(11) . ? N1 C11 1.357(6) . ? C11 C12 1.378(2) . ? C11 C16 1.380(2) . ? C12 C13 1.364(2) . ? C12 H12A 0.9300 . ? C13 C14 1.394(2) . ? C13 H13A 0.9300 . ? C14 C15 1.391(2) . ? C14 C17 1.464(2) . ? C15 C16 1.374(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 123.3(15) . . ? N11 Cl1 O12 63.3(12) . . ? O11 Cl1 O12 170.9(6) . . ? N11 Cl1 C1 23.9(11) . . ? O11 Cl1 C1 100.8(5) . . ? O12 Cl1 C1 86.55(18) . . ? Cl1 N11 O12 90.0(12) . . ? Cl1 N11 O11 33.5(10) . . ? O12 N11 O11 123.1(6) . . ? Cl1 N11 C1 146.0(16) . . ? O12 N11 C1 122.9(7) . . ? O11 N11 C1 113.9(7) . . ? Cl1 O11 N11 23.2(5) . . ? N11 O12 Cl1 26.7(3) . . ? N11 C1 C2 114.3(4) . . ? N11 C1 C6 124.0(4) . . ? C2 C1 C6 121.67(19) . . ? N11 C1 Cl1 10.1(5) . . ? C2 C1 Cl1 124.01(19) . . ? C6 C1 Cl1 114.3(2) . . ? C3 C2 C1 118.98(18) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 121.86(19) . . ? C2 C3 H3A 119.1 . . ? C4 C3 H3A 119.1 . . ? C5 C4 C3 117.04(18) . . ? C5 C4 C7 119.50(16) . . ? C3 C4 C7 123.46(18) . . ? C6 C5 C4 122.47(17) . . ? C6 C5 H5A 118.8 . . ? C4 C5 H5A 118.8 . . ? C5 C6 C1 117.97(19) . . ? C5 C6 H6A 121.0 . . ? C1 C6 H6A 121.0 . . ? C17 C7 C4 126.8(2) . . ? C17 C7 H7A 116.6 . . ? C4 C7 H7A 116.6 . . ? N1 Cl11 O1 123.3(15) . . ? N1 Cl11 O2 63.3(12) . . ? O1 Cl11 O2 170.9(6) . . ? N1 Cl11 C11 23.9(11) . . ? O1 Cl11 C11 100.8(5) . . ? O2 Cl11 C11 86.55(18) . . ? Cl11 N1 O2 90.0(12) . . ? Cl11 N1 O1 33.5(10) . . ? O2 N1 O1 123.1(6) . . ? Cl11 N1 C11 146.0(16) . . ? O2 N1 C11 122.9(7) . . ? O1 N1 C11 113.9(7) . . ? Cl11 O1 N1 23.2(5) . . ? N1 O2 Cl11 26.7(3) . . ? N1 C11 C12 114.3(4) . . ? N1 C11 C16 124.0(4) . . ? C12 C11 C16 121.67(19) . . ? N1 C11 Cl11 10.1(5) . . ? C12 C11 Cl11 124.01(19) . . ? C16 C11 Cl11 114.3(2) . . ? C13 C12 C11 118.98(18) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C14 121.86(19) . . ? C12 C13 H13A 119.1 . . ? C14 C13 H13A 119.1 . . ? C15 C14 C13 117.04(18) . . ? C15 C14 C17 119.50(16) . . ? C13 C14 C17 123.46(18) . . ? C16 C15 C14 122.47(17) . . ? C16 C15 H15A 118.8 . . ? C14 C15 H15A 118.8 . . ? C15 C16 C11 117.97(19) . . ? C15 C16 H16A 121.0 . . ? C11 C16 H16A 121.0 . . ? C7 C17 C14 126.8(2) . . ? C7 C17 H17A 116.6 . . ? C14 C17 H17A 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.8(9) . . . . ? C1 Cl1 N11 O12 -166(3) . . . . ? O12 Cl1 N11 O11 -172.8(9) . . . . ? C1 Cl1 N11 O11 21(4) . . . . ? O11 Cl1 N11 C1 -21(4) . . . . ? O12 Cl1 N11 C1 166(3) . . . . ? O12 Cl1 O11 N11 135(5) . . . . ? C1 Cl1 O11 N11 -8.7(15) . . . . ? O12 N11 O11 Cl1 -8.6(11) . . . . ? C1 N11 O11 Cl1 167(2) . . . . ? O11 N11 O12 Cl1 4.7(6) . . . . ? C1 N11 O12 Cl1 -171(2) . . . . ? O11 Cl1 O12 N11 -139(5) . . . . ? C1 Cl1 O12 N11 5.7(13) . . . . ? Cl1 N11 C1 C2 -164(3) . . . . ? O12 N11 C1 C2 -1.4(10) . . . . ? O11 N11 C1 C2 -177.1(7) . . . . ? Cl1 N11 C1 C6 19(3) . . . . ? O12 N11 C1 C6 -178.1(6) . . . . ? O11 N11 C1 C6 6.2(11) . . . . ? O12 N11 C1 Cl1 163(4) . . . . ? O11 N11 C1 Cl1 -13(2) . . . . ? O11 Cl1 C1 N11 162(3) . . . . ? O12 Cl1 C1 N11 -13(3) . . . . ? N11 Cl1 C1 C2 17(3) . . . . ? O11 Cl1 C1 C2 179.1(6) . . . . ? O12 Cl1 C1 C2 4.5(3) . . . . ? N11 Cl1 C1 C6 -163(3) . . . . ? O11 Cl1 C1 C6 -0.9(6) . . . . ? O12 Cl1 C1 C6 -175.5(2) . . . . ? N11 C1 C2 C3 -177.7(5) . . . . ? C6 C1 C2 C3 -1.0(3) . . . . ? Cl1 C1 C2 C3 179.0(2) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C2 C3 C4 C7 179.70(17) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C7 C4 C5 C6 -179.73(16) . . . . ? C4 C5 C6 C1 -0.8(3) . . . . ? N11 C1 C6 C5 177.4(5) . . . . ? C2 C1 C6 C5 0.9(3) . . . . ? Cl1 C1 C6 C5 -179.05(19) . . . . ? C5 C4 C7 C17 175.9(2) . . . . ? C3 C4 C7 C17 -4.5(4) . . . . ? O1 Cl11 N1 O2 -172.8(9) . . . . ? C11 Cl11 N1 O2 166(3) . . . . ? O2 Cl11 N1 O1 172.8(9) . . . . ? C11 Cl11 N1 O1 -21(4) . . . . ? O1 Cl11 N1 C11 21(4) . . . . ? O2 Cl11 N1 C11 -166(3) . . . . ? O2 Cl11 O1 N1 -135(5) . . . . ? C11 Cl11 O1 N1 8.7(15) . . . . ? O2 N1 O1 Cl11 8.6(11) . . . . ? C11 N1 O1 Cl11 -167(2) . . . . ? O1 N1 O2 Cl11 -4.7(6) . . . . ? C11 N1 O2 Cl11 171(2) . . . . ? O1 Cl11 O2 N1 139(5) . . . . ? C11 Cl11 O2 N1 -5.7(13) . . . . ? Cl11 N1 C11 C12 164(3) . . . . ? O2 N1 C11 C12 1.4(10) . . . . ? O1 N1 C11 C12 177.1(7) . . . . ? Cl11 N1 C11 C16 -19(3) . . . . ? O2 N1 C11 C16 178.1(6) . . . . ? O1 N1 C11 C16 -6.2(11) . . . . ? O2 N1 C11 Cl11 -163(4) . . . . ? O1 N1 C11 Cl11 13(2) . . . . ? O1 Cl11 C11 N1 -162(3) . . . . ? O2 Cl11 C11 N1 13(3) . . . . ? N1 Cl11 C11 C12 -17(3) . . . . ? O1 Cl11 C11 C12 -179.1(6) . . . . ? O2 Cl11 C11 C12 -4.5(3) . . . . ? N1 Cl11 C11 C16 163(3) . . . . ? O1 Cl11 C11 C16 0.9(6) . . . . ? O2 Cl11 C11 C16 175.5(2) . . . . ? N1 C11 C12 C13 177.7(5) . . . . ? C16 C11 C12 C13 1.0(3) . . . . ? Cl11 C11 C12 C13 -179.0(2) . . . . ? C11 C12 C13 C14 -0.9(3) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ? C12 C13 C14 C17 -179.70(17) . . . . ? C13 C14 C15 C16 -0.6(3) . . . . ? C17 C14 C15 C16 179.73(16) . . . . ? C14 C15 C16 C11 0.8(3) . . . . ? N1 C11 C16 C15 -177.4(5) . . . . ? C12 C11 C16 C15 -0.9(3) . . . . ? Cl11 C11 C16 C15 179.05(19) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.9(2) . . . . ? C13 C14 C17 C7 4.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.899 _diffrn_reflns_theta_full 27.82 _diffrn_measured_fraction_theta_full 0.899 _refine_diff_density_max 0.109 _refine_diff_density_min -0.102 _refine_diff_density_rms 0.026 # start Validation Reply Form _vrf_SYMMG02_CNS-TolI-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-TolI-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.90 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; # end Validation Reply Form #===END data_CNS-TolI-big-A1 _database_code_depnum_ccdc_archive 'CCDC 761212' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'A 1' _symmetry_space_group_name_Hall 'A 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, y+1/2, z+1/2' _cell_length_a 3.9236(3) _cell_length_b 25.9480(8) _cell_length_c 24.4812(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.175(3) _cell_angle_gamma 90.00 _cell_volume 2488.6(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13907 _cell_measurement_theta_min 3.1395 _cell_measurement_theta_max 24.9455 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.547691 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'refined from Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4072 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.82 _reflns_number_total 3344 _reflns_number_gt 1604 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction 'SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0311P)^2^+6.7417P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(3) _refine_ls_number_reflns 3344 _refine_ls_number_parameters 72 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1429 _refine_ls_R_factor_gt 0.0709 _refine_ls_wR_factor_ref 0.1536 _refine_ls_wR_factor_gt 0.1290 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1A Cl 0.3678 -0.2304 -0.0875 0.1075(8) Uani 0.563(19) 1 d P A 1 N1A N -0.3731 0.2076 0.0864 0.0809(15) Uani 0.563(19) 1 d P A 1 O1A O -0.3094 0.2486 0.0620 0.128(2) Uani 0.563(19) 1 d P A 1 O2A O -0.5003 0.2066 0.1288 0.1092(14) Uani 0.563(19) 1 d P A 1 Cl1E Cl -0.3678 0.2304 0.0875 0.1075(8) Uani 0.437(19) 1 d P A 2 N1E N 0.3731 -0.2076 -0.0865 0.0809(15) Uani 0.437(19) 1 d P A 2 O1E O 0.3094 -0.2486 -0.0620 0.128(2) Uani 0.437(19) 1 d P A 2 O2E O 0.5003 -0.2066 -0.1288 0.1092(14) Uani 0.437(19) 1 d P A 2 C1A C 0.2606 -0.1646 -0.0616 0.0695(6) Uani 1 1 d . A 2 C2A C 0.3154 -0.1195 -0.0896 0.0795(7) Uani 1 1 d . A 2 H2A H 0.4142 -0.1203 -0.1233 0.095 Uiso 1 1 calc R A 2 C3A C 0.2226 -0.0739 -0.0672 0.0729(7) Uani 1 1 d . A 2 H3A H 0.2566 -0.0435 -0.0862 0.087 Uiso 1 1 calc R A 2 C4A C 0.0781 -0.0715 -0.0164 0.0620(6) Uani 1 1 d . A 2 C5A C 0.0286 -0.1180 0.0103 0.0707(6) Uani 1 1 d . A 2 H5A H -0.0694 -0.1175 0.0440 0.085 Uiso 1 1 calc R A 2 C6A C 0.1192 -0.1646 -0.0112 0.0738(7) Uani 1 1 d . A 2 H6A H 0.0863 -0.1951 0.0076 0.089 Uiso 1 1 calc R A 2 C7A C -0.0233 -0.0232 0.0091 0.0720(6) Uani 1 1 d . A 2 H7A H -0.1324 -0.0261 0.0417 0.086 Uiso 1 1 calc R A 2 C11A C -0.2606 0.1646 0.0616 0.0695(6) Uani 1 1 d . A 2 C12A C -0.3154 0.1195 0.0896 0.0795(7) Uani 1 1 d . A 2 H12A H -0.4142 0.1203 0.1232 0.095 Uiso 1 1 calc R A 2 C13A C -0.2226 0.0738 0.0671 0.0729(7) Uani 1 1 d . A 2 H13A H -0.2566 0.0435 0.0862 0.087 Uiso 1 1 calc R A 2 C14A C -0.0781 0.0715 0.0164 0.0620(6) Uani 1 1 d . A 2 C15A C -0.0286 0.1180 -0.0103 0.0707(6) Uani 1 1 d . A 2 H15A H 0.0694 0.1175 -0.0441 0.085 Uiso 1 1 calc R A 2 C16A C -0.1192 0.1646 0.0112 0.0738(7) Uani 1 1 d . A 2 H16A H -0.0862 0.1952 -0.0076 0.089 Uiso 1 1 calc R A 2 C17A C 0.0233 0.0232 -0.0091 0.0720(6) Uani 1 1 d . A 2 H17A H 0.1324 0.0261 -0.0417 0.086 Uiso 1 1 calc R A 2 Cl1B Cl 0.3678 -0.2304 0.4125 0.1075(8) Uani 0.316(19) 1 d P B 3 N1B N -0.3731 0.2076 0.5864 0.0809(15) Uani 0.316(19) 1 d P B 3 O1B O -0.3094 0.2486 0.5620 0.128(2) Uani 0.316(19) 1 d P B 3 O2B O -0.5003 0.2066 0.6288 0.1092(14) Uani 0.316(19) 1 d P B 3 Cl1F Cl -0.3678 0.2304 0.5875 0.1075(8) Uani 0.684(19) 1 d P B 4 N1F N 0.3731 -0.2076 0.4135 0.0809(15) Uani 0.684(19) 1 d P B 4 O1F O 0.3094 -0.2486 0.4380 0.128(2) Uani 0.684(19) 1 d P B 4 O2F O 0.5003 -0.2066 0.3712 0.1092(14) Uani 0.684(19) 1 d P B 4 C1B C 0.2606 -0.1646 0.4384 0.0695(6) Uani 1 1 d . B 4 C2B C 0.3154 -0.1195 0.4104 0.0795(7) Uani 1 1 d . B 4 H2B H 0.4142 -0.1203 0.3767 0.095 Uiso 1 1 calc R B 4 C3B C 0.2226 -0.0739 0.4328 0.0729(7) Uani 1 1 d . B 4 H3B H 0.2566 -0.0435 0.4138 0.087 Uiso 1 1 calc R B 4 C4B C 0.0781 -0.0715 0.4836 0.0620(6) Uani 1 1 d . B 4 C5B C 0.0286 -0.1180 0.5103 0.0707(6) Uani 1 1 d . B 4 H5B H -0.0694 -0.1175 0.5440 0.085 Uiso 1 1 calc R B 4 C6B C 0.1192 -0.1646 0.4888 0.0738(7) Uani 1 1 d . B 4 H6B H 0.0863 -0.1951 0.5076 0.089 Uiso 1 1 calc R B 4 C7B C -0.0233 -0.0232 0.5091 0.0720(6) Uani 1 1 d . B 4 H7B H -0.1324 -0.0261 0.5417 0.086 Uiso 1 1 calc R B 4 C11B C -0.2606 0.1646 0.5616 0.0695(6) Uani 1 1 d . B 4 C12B C -0.3154 0.1195 0.5896 0.0795(7) Uani 1 1 d . B 4 H12B H -0.4142 0.1203 0.6232 0.095 Uiso 1 1 calc R B 4 C13B C -0.2226 0.0738 0.5671 0.0729(7) Uani 1 1 d . B 4 H13B H -0.2566 0.0435 0.5862 0.087 Uiso 1 1 calc R B 4 C14B C -0.0781 0.0715 0.5164 0.0620(6) Uani 1 1 d . B 4 C15B C -0.0286 0.1180 0.4897 0.0707(6) Uani 1 1 d . B 4 H15B H 0.0694 0.1175 0.4559 0.085 Uiso 1 1 calc R B 4 C16B C -0.1192 0.1646 0.5112 0.0738(7) Uani 1 1 d . B 4 H16B H -0.0862 0.1952 0.4924 0.089 Uiso 1 1 calc R B 4 C17B C 0.0233 0.0232 0.4909 0.0720(6) Uani 1 1 d . B 4 H17B H 0.1324 0.0261 0.4583 0.086 Uiso 1 1 calc R B 4 Cl1C Cl -0.3678 0.0196 0.3375 0.1075(8) Uani 0.32(7) 1 d P C 5 N1C N 0.3731 0.4576 0.1635 0.0809(15) Uani 0.32(7) 1 d P C 5 O1C O 0.3094 0.4986 0.1881 0.128(2) Uani 0.32(7) 1 d P C 5 O2C O 0.5003 0.4566 0.1212 0.1092(14) Uani 0.32(7) 1 d P C 5 Cl1G Cl 0.3678 0.4804 0.1625 0.1075(8) Uani 0.68(7) 1 d P C 6 N1G N -0.3731 0.0424 0.3364 0.0809(15) Uani 0.68(7) 1 d P C 6 O1G O -0.3094 0.0014 0.3120 0.128(2) Uani 0.68(7) 1 d P C 6 O2G O -0.5003 0.0434 0.3788 0.1092(14) Uani 0.68(7) 1 d P C 6 C1C C -0.2606 0.0854 0.3116 0.0695(6) Uani 1 1 d . C 6 C2C C -0.3154 0.1305 0.3396 0.0795(7) Uani 1 1 d . C 6 H2C H -0.4142 0.1297 0.3732 0.095 Uiso 1 1 calc R C 6 C3C C -0.2226 0.1761 0.3171 0.0729(7) Uani 1 1 d . C 6 H3C H -0.2566 0.2065 0.3362 0.087 Uiso 1 1 calc R C 6 C4C C -0.0781 0.1785 0.2664 0.0620(6) Uani 1 1 d . C 6 C5C C -0.0286 0.1320 0.2397 0.0707(6) Uani 1 1 d . C 6 H5C H 0.0694 0.1325 0.2059 0.085 Uiso 1 1 calc R C 6 C6C C -0.1192 0.0854 0.2612 0.0738(7) Uani 1 1 d . C 6 H6C H -0.0862 0.0548 0.2424 0.089 Uiso 1 1 calc R C 6 C7C C 0.0233 0.2268 0.2409 0.0720(6) Uani 1 1 d . C 6 H7C H 0.1324 0.2240 0.2083 0.086 Uiso 1 1 calc R C 6 C11C C 0.2606 0.4146 0.1884 0.0695(6) Uani 1 1 d . C 6 C12C C 0.3154 0.3695 0.1604 0.0795(7) Uani 1 1 d . C 6 H12C H 0.4142 0.3703 0.1268 0.095 Uiso 1 1 calc R C 6 C13C C 0.2226 0.3239 0.1829 0.0729(7) Uani 1 1 d . C 6 H13C H 0.2566 0.2935 0.1638 0.087 Uiso 1 1 calc R C 6 C14C C 0.0781 0.3215 0.2336 0.0620(6) Uani 1 1 d . C 6 C15C C 0.0286 0.3680 0.2603 0.0707(6) Uani 1 1 d . C 6 H15C H -0.0694 0.3675 0.2940 0.085 Uiso 1 1 calc R C 6 C16C C 0.1192 0.4145 0.2388 0.0738(7) Uani 1 1 d . C 6 H16C H 0.0863 0.4451 0.2576 0.089 Uiso 1 1 calc R C 6 C17C C -0.0233 0.2732 0.2591 0.0720(6) Uani 1 1 d . C 6 H17C H -0.1324 0.2760 0.2917 0.086 Uiso 1 1 calc R C 6 Cl1D Cl -0.3678 0.0196 -0.1625 0.1075(8) Uani 0.38(7) 1 d P D 7 N1D N 0.3731 0.4576 -0.3365 0.0809(15) Uani 0.38(7) 1 d P D 7 O1D O 0.3094 0.4986 -0.3119 0.128(2) Uani 0.38(7) 1 d P D 7 O2D O 0.5003 0.4566 -0.3788 0.1092(14) Uani 0.38(7) 1 d P D 7 Cl1H Cl 0.3678 0.4804 -0.3375 0.1075(8) Uani 0.62(7) 1 d P D 8 N1H N -0.3731 0.0424 -0.1636 0.0809(15) Uani 0.62(7) 1 d P D 8 O1H O -0.3094 0.0014 -0.1880 0.128(2) Uani 0.62(7) 1 d P D 8 O2H O -0.5003 0.0434 -0.1212 0.1092(14) Uani 0.62(7) 1 d P D 8 C1D C -0.2606 0.0854 -0.1884 0.0695(6) Uani 1 1 d . D 8 C2D C -0.3154 0.1305 -0.1604 0.0795(7) Uani 1 1 d . D 8 H2D H -0.4142 0.1297 -0.1268 0.095 Uiso 1 1 calc R D 8 C3D C -0.2226 0.1761 -0.1829 0.0729(7) Uani 1 1 d . D 8 H3D H -0.2566 0.2065 -0.1638 0.087 Uiso 1 1 calc R D 8 C4D C -0.0781 0.1785 -0.2336 0.0620(6) Uani 1 1 d . D 8 C5D C -0.0286 0.1320 -0.2603 0.0707(6) Uani 1 1 d . D 8 H5D H 0.0694 0.1325 -0.2941 0.085 Uiso 1 1 calc R D 8 C6D C -0.1192 0.0854 -0.2388 0.0738(7) Uani 1 1 d . D 8 H6D H -0.0862 0.0548 -0.2576 0.089 Uiso 1 1 calc R D 8 C7D C 0.0233 0.2268 -0.2591 0.0720(6) Uani 1 1 d . D 8 H7D H 0.1324 0.2240 -0.2917 0.086 Uiso 1 1 calc R D 8 C11D C 0.2606 0.4146 -0.3116 0.0695(6) Uani 1 1 d . D 8 C12D C 0.3154 0.3695 -0.3396 0.0795(7) Uani 1 1 d . D 8 H12D H 0.4142 0.3703 -0.3732 0.095 Uiso 1 1 calc R D 8 C13D C 0.2226 0.3239 -0.3171 0.0729(7) Uani 1 1 d . D 8 H13D H 0.2566 0.2935 -0.3362 0.087 Uiso 1 1 calc R D 8 C14D C 0.0781 0.3215 -0.2664 0.0620(6) Uani 1 1 d . D 8 C15D C 0.0286 0.3680 -0.2397 0.0707(6) Uani 1 1 d . D 8 H15D H -0.0694 0.3675 -0.2060 0.085 Uiso 1 1 calc R D 8 C16D C 0.1192 0.4145 -0.2612 0.0738(7) Uani 1 1 d . D 8 H16D H 0.0863 0.4451 -0.2424 0.089 Uiso 1 1 calc R D 8 C17D C -0.0233 0.2732 -0.2409 0.0720(6) Uani 1 1 d . D 8 H17D H -0.1324 0.2760 -0.2083 0.086 Uiso 1 1 calc R D 8 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1A 0.1089(14) 0.0842(12) 0.1296(17) -0.0455(12) 0.0091(12) 0.0149(10) N1A 0.086(4) 0.056(3) 0.100(4) 0.000(2) -0.004(3) -0.007(2) O1A 0.168(5) 0.076(2) 0.145(4) 0.011(3) 0.045(3) 0.009(3) O2A 0.153(4) 0.092(2) 0.087(3) -0.025(2) 0.037(3) 0.018(2) Cl1E 0.1089(14) 0.0842(12) 0.1296(17) -0.0455(12) 0.0091(12) 0.0149(10) N1E 0.086(4) 0.056(3) 0.100(4) 0.000(2) -0.004(3) -0.007(2) O1E 0.168(5) 0.076(2) 0.145(4) 0.011(3) 0.045(3) 0.009(3) O2E 0.153(4) 0.092(2) 0.087(3) -0.025(2) 0.037(3) 0.018(2) C1A 0.0544(15) 0.0793(15) 0.0741(16) -0.0157(12) -0.0042(12) 0.0067(13) C2A 0.0720(17) 0.1010(18) 0.0664(16) -0.0025(13) 0.0107(13) 0.0001(15) C3A 0.0630(15) 0.0854(15) 0.0707(16) 0.0099(13) 0.0069(12) -0.0020(13) C4A 0.0488(13) 0.0755(14) 0.0615(15) -0.0062(12) 0.0008(11) -0.0010(11) C5A 0.0667(15) 0.0834(15) 0.0629(15) 0.0014(12) 0.0100(12) -0.0020(13) C6A 0.0724(17) 0.0736(14) 0.0756(18) 0.0036(12) 0.0050(13) 0.0025(13) C7A 0.0617(14) 0.0815(15) 0.0729(16) 0.0068(13) 0.0051(12) -0.0024(14) C11A 0.0544(15) 0.0793(15) 0.0741(16) -0.0157(12) -0.0042(12) 0.0067(13) C12A 0.0720(17) 0.1010(18) 0.0664(16) -0.0025(13) 0.0107(13) 0.0001(15) C13A 0.0630(15) 0.0854(15) 0.0707(16) 0.0099(13) 0.0069(12) -0.0020(13) C14A 0.0488(13) 0.0755(14) 0.0615(15) -0.0062(12) 0.0008(11) -0.0010(11) C15A 0.0667(15) 0.0834(15) 0.0629(15) 0.0014(12) 0.0100(12) -0.0020(13) C16A 0.0724(17) 0.0736(14) 0.0756(18) 0.0036(12) 0.0050(13) 0.0025(13) C17A 0.0617(14) 0.0815(15) 0.0729(16) 0.0068(13) 0.0051(12) -0.0024(14) Cl1B 0.1089(14) 0.0842(12) 0.1296(17) -0.0455(12) 0.0091(12) 0.0149(10) N1B 0.086(4) 0.056(3) 0.100(4) 0.000(2) -0.004(3) -0.007(2) O1B 0.168(5) 0.076(2) 0.145(4) 0.011(3) 0.045(3) 0.009(3) O2B 0.153(4) 0.092(2) 0.087(3) -0.025(2) 0.037(3) 0.018(2) Cl1F 0.1089(14) 0.0842(12) 0.1296(17) -0.0455(12) 0.0091(12) 0.0149(10) N1F 0.086(4) 0.056(3) 0.100(4) 0.000(2) -0.004(3) -0.007(2) O1F 0.168(5) 0.076(2) 0.145(4) 0.011(3) 0.045(3) 0.009(3) O2F 0.153(4) 0.092(2) 0.087(3) -0.025(2) 0.037(3) 0.018(2) C1B 0.0544(15) 0.0793(15) 0.0741(16) -0.0157(12) -0.0042(12) 0.0067(13) C2B 0.0720(17) 0.1010(18) 0.0664(16) -0.0025(13) 0.0107(13) 0.0001(15) C3B 0.0630(15) 0.0854(15) 0.0707(16) 0.0099(13) 0.0069(12) -0.0020(13) C4B 0.0488(13) 0.0755(14) 0.0615(15) -0.0062(12) 0.0008(11) -0.0010(11) C5B 0.0667(15) 0.0834(15) 0.0629(15) 0.0014(12) 0.0100(12) -0.0020(13) C6B 0.0724(17) 0.0736(14) 0.0756(18) 0.0036(12) 0.0050(13) 0.0025(13) C7B 0.0617(14) 0.0815(15) 0.0729(16) 0.0068(13) 0.0051(12) -0.0024(14) C11B 0.0544(15) 0.0793(15) 0.0741(16) -0.0157(12) -0.0042(12) 0.0067(13) C12B 0.0720(17) 0.1010(18) 0.0664(16) -0.0025(13) 0.0107(13) 0.0001(15) C13B 0.0630(15) 0.0854(15) 0.0707(16) 0.0099(13) 0.0069(12) -0.0020(13) C14B 0.0488(13) 0.0755(14) 0.0615(15) -0.0062(12) 0.0008(11) -0.0010(11) C15B 0.0667(15) 0.0834(15) 0.0629(15) 0.0014(12) 0.0100(12) -0.0020(13) C16B 0.0724(17) 0.0736(14) 0.0756(18) 0.0036(12) 0.0050(13) 0.0025(13) C17B 0.0617(14) 0.0815(15) 0.0729(16) 0.0068(13) 0.0051(12) -0.0024(14) Cl1C 0.1089(14) 0.0842(12) 0.1296(17) 0.0455(12) 0.0091(12) -0.0149(10) N1C 0.086(4) 0.056(3) 0.100(4) 0.000(2) -0.004(3) 0.007(2) O1C 0.168(5) 0.076(2) 0.145(4) -0.011(3) 0.045(3) -0.009(3) O2C 0.153(4) 0.092(2) 0.087(3) 0.025(2) 0.037(3) -0.018(2) Cl1G 0.1089(14) 0.0842(12) 0.1296(17) 0.0455(12) 0.0091(12) -0.0149(10) N1G 0.086(4) 0.056(3) 0.100(4) 0.000(2) -0.004(3) 0.007(2) O1G 0.168(5) 0.076(2) 0.145(4) -0.011(3) 0.045(3) -0.009(3) O2G 0.153(4) 0.092(2) 0.087(3) 0.025(2) 0.037(3) -0.018(2) C1C 0.0544(15) 0.0793(15) 0.0741(16) 0.0157(12) -0.0042(12) -0.0067(13) C2C 0.0720(17) 0.1010(18) 0.0664(16) 0.0025(13) 0.0107(13) -0.0001(15) C3C 0.0630(15) 0.0854(15) 0.0707(16) -0.0099(13) 0.0069(12) 0.0020(13) C4C 0.0488(13) 0.0755(14) 0.0615(15) 0.0062(12) 0.0008(11) 0.0010(11) C5C 0.0667(15) 0.0834(15) 0.0629(15) -0.0014(12) 0.0100(12) 0.0020(13) C6C 0.0724(17) 0.0736(14) 0.0756(18) -0.0036(12) 0.0050(13) -0.0025(13) C7C 0.0617(14) 0.0815(15) 0.0729(16) -0.0068(13) 0.0051(12) 0.0024(14) C11C 0.0544(15) 0.0793(15) 0.0741(16) 0.0157(12) -0.0042(12) -0.0067(13) C12C 0.0720(17) 0.1010(18) 0.0664(16) 0.0025(13) 0.0107(13) -0.0001(15) C13C 0.0630(15) 0.0854(15) 0.0707(16) -0.0099(13) 0.0069(12) 0.0020(13) C14C 0.0488(13) 0.0755(14) 0.0615(15) 0.0062(12) 0.0008(11) 0.0010(11) C15C 0.0667(15) 0.0834(15) 0.0629(15) -0.0014(12) 0.0100(12) 0.0020(13) C16C 0.0724(17) 0.0736(14) 0.0756(18) -0.0036(12) 0.0050(13) -0.0025(13) C17C 0.0617(14) 0.0815(15) 0.0729(16) -0.0068(13) 0.0051(12) 0.0024(14) Cl1D 0.1089(14) 0.0842(12) 0.1296(17) 0.0455(12) 0.0091(12) -0.0149(10) N1D 0.086(4) 0.056(3) 0.100(4) 0.000(2) -0.004(3) 0.007(2) O1D 0.168(5) 0.076(2) 0.145(4) -0.011(3) 0.045(3) -0.009(3) O2D 0.153(4) 0.092(2) 0.087(3) 0.025(2) 0.037(3) -0.018(2) Cl1H 0.1089(14) 0.0842(12) 0.1296(17) 0.0455(12) 0.0091(12) -0.0149(10) N1H 0.086(4) 0.056(3) 0.100(4) 0.000(2) -0.004(3) 0.007(2) O1H 0.168(5) 0.076(2) 0.145(4) -0.011(3) 0.045(3) -0.009(3) O2H 0.153(4) 0.092(2) 0.087(3) 0.025(2) 0.037(3) -0.018(2) C1D 0.0544(15) 0.0793(15) 0.0741(16) 0.0157(12) -0.0042(12) -0.0067(13) C2D 0.0720(17) 0.1010(18) 0.0664(16) 0.0025(13) 0.0107(13) -0.0001(15) C3D 0.0630(15) 0.0854(15) 0.0707(16) -0.0099(13) 0.0069(12) 0.0020(13) C4D 0.0488(13) 0.0755(14) 0.0615(15) 0.0062(12) 0.0008(11) 0.0010(11) C5D 0.0667(15) 0.0834(15) 0.0629(15) -0.0014(12) 0.0100(12) 0.0020(13) C6D 0.0724(17) 0.0736(14) 0.0756(18) -0.0036(12) 0.0050(13) -0.0025(13) C7D 0.0617(14) 0.0815(15) 0.0729(16) -0.0068(13) 0.0051(12) 0.0024(14) C11D 0.0544(15) 0.0793(15) 0.0741(16) 0.0157(12) -0.0042(12) -0.0067(13) C12D 0.0720(17) 0.1010(18) 0.0664(16) 0.0025(13) 0.0107(13) -0.0001(15) C13D 0.0630(15) 0.0854(15) 0.0707(16) -0.0099(13) 0.0069(12) 0.0020(13) C14D 0.0488(13) 0.0755(14) 0.0615(15) 0.0062(12) 0.0008(11) 0.0010(11) C15D 0.0667(15) 0.0834(15) 0.0629(15) -0.0014(12) 0.0100(12) 0.0020(13) C16D 0.0724(17) 0.0736(14) 0.0756(18) -0.0036(12) 0.0050(13) -0.0025(13) C17D 0.0617(14) 0.0815(15) 0.0729(16) -0.0068(13) 0.0051(12) 0.0024(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1A O2A 1.1757 . ? N1A O1A 1.2533 . ? Cl1E C11A 1.8766 . ? N1E O2E 1.1745 . ? N1E O1E 1.2535 . ? N1E C1A 1.3572 . ? C1A C2A 1.3781 . ? C1A C6A 1.3802 . ? C2A C3A 1.3644 . ? C2A H2A 0.9300 . ? C3A C4A 1.3947 . ? C3A H3A 0.9300 . ? C4A C5A 1.3914 . ? C4A C7A 1.4636 . ? C5A C6A 1.3739 . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? C7A C17A 1.3010 . ? C7A H7A 0.9300 . ? C11A C12A 1.3779 . ? C11A C16A 1.3797 . ? C12A C13A 1.3644 . ? C12A H12A 0.9300 . ? C13A C14A 1.3950 . ? C13A H13A 0.9300 . ? C14A C15A 1.3913 . ? C14A C17A 1.4638 . ? C15A C16A 1.3743 . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? C17A H17A 0.9300 . ? N1B O2B 1.1757 . ? N1B O1B 1.2533 . ? Cl1F C11B 1.8766 . ? N1F O2F 1.1745 . ? N1F O1F 1.2535 . ? N1F C1B 1.3572 . ? C1B C2B 1.3781 . ? C1B C6B 1.3802 . ? C2B C3B 1.3644 . ? C2B H2B 0.9300 . ? C3B C4B 1.3947 . ? C3B H3B 0.9300 . ? C4B C5B 1.3914 . ? C4B C7B 1.4636 . ? C5B C6B 1.3739 . ? C5B H5B 0.9300 . ? C6B H6B 0.9300 . ? C7B C17B 1.3010 . ? C7B H7B 0.9300 . ? C11B C12B 1.3779 . ? C11B C16B 1.3797 . ? C12B C13B 1.3644 . ? C12B H12B 0.9300 . ? C13B C14B 1.3950 . ? C13B H13B 0.9300 . ? C14B C15B 1.3913 . ? C14B C17B 1.4638 . ? C15B C16B 1.3743 . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? C17B H17B 0.9300 . ? N1C O2C 1.1741 . ? N1C O1C 1.2537 . ? Cl1G C11C 1.8772 . ? N1G O2G 1.1752 . ? N1G O1G 1.2531 . ? N1G C1C 1.3570 . ? C1C C2C 1.3779 . ? C1C C6C 1.3797 . ? C2C C3C 1.3643 . ? C2C H2C 0.9300 . ? C3C C4C 1.3950 . ? C3C H3C 0.9300 . ? C4C C5C 1.3913 . ? C4C C7C 1.4641 . ? C5C C6C 1.3743 . ? C5C H5C 0.9300 . ? C6C H6C 0.9300 . ? C7C C17C 1.3000 . ? C7C H7C 0.9300 . ? C11C C12C 1.3775 . ? C11C C16C 1.3799 . ? C12C C13C 1.3644 . ? C12C H12C 0.9300 . ? C13C C14C 1.3942 . ? C13C H13C 0.9300 . ? C14C C15C 1.3913 . ? C14C C17C 1.4645 . ? C15C C16C 1.3733 . ? C15C H15C 0.9300 . ? C16C H16C 0.9300 . ? C17C H17C 0.9300 . ? N1D O2D 1.1741 . ? N1D O1D 1.2537 . ? Cl1H C11D 1.8772 . ? N1H O2H 1.1752 . ? N1H O1H 1.2531 . ? N1H C1D 1.3570 . ? C1D C2D 1.3779 . ? C1D C6D 1.3797 . ? C2D C3D 1.3643 . ? C2D H2D 0.9300 . ? C3D C4D 1.3950 . ? C3D H3D 0.9300 . ? C4D C5D 1.3913 . ? C4D C7D 1.4641 . ? C5D C6D 1.3743 . ? C5D H5D 0.9300 . ? C6D H6D 0.9300 . ? C7D C17D 1.3000 . ? C7D H7D 0.9300 . ? C11D C12D 1.3775 . ? C11D C16D 1.3799 . ? C12D C13D 1.3644 . ? C12D H12D 0.9300 . ? C13D C14D 1.3942 . ? C13D H13D 0.9300 . ? C14D C15D 1.3913 . ? C14D C17D 1.4645 . ? C15D C16D 1.3733 . ? C15D H15D 0.9300 . ? C16D H16D 0.9300 . ? C17D H17D 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2A N1A O1A 123.110(2) . . ? O2E N1E O1E 123.120(2) . . ? O2E N1E C1A 122.846(2) . . ? O1E N1E C1A 113.887(3) . . ? N1E C1A C2A 114.287(3) . . ? N1E C1A C6A 123.941(2) . . ? C2A C1A C6A 121.686(1) . . ? C3A C2A C1A 118.983(2) . . ? C3A C2A H2A 120.5 . . ? C1A C2A H2A 120.5 . . ? C2A C3A C4A 121.851(2) . . ? C2A C3A H3A 119.1 . . ? C4A C3A H3A 119.1 . . ? C5A C4A C3A 117.046(2) . . ? C5A C4A C7A 119.470(3) . . ? C3A C4A C7A 123.483(2) . . ? C6A C5A C4A 122.464(2) . . ? C6A C5A H5A 118.8 . . ? C4A C5A H5A 118.8 . . ? C5A C6A C1A 117.961(2) . . ? C5A C6A H6A 121.0 . . ? C1A C6A H6A 121.0 . . ? C17A C7A C4A 126.824(2) . . ? C17A C7A H7A 116.6 . . ? C4A C7A H7A 116.6 . . ? C12A C11A C16A 121.669(2) . . ? C12A C11A Cl1E 124.022(2) . . ? C16A C11A Cl1E 114.309(1) . . ? C13A C12A C11A 119.009(2) . . ? C13A C12A H12A 120.5 . . ? C11A C12A H12A 120.5 . . ? C12A C13A C14A 121.835(1) . . ? C12A C13A H13A 119.1 . . ? C14A C13A H13A 119.1 . . ? C15A C14A C13A 117.044(2) . . ? C15A C14A C17A 119.510(3) . . ? C13A C14A C17A 123.445(2) . . ? C16A C15A C14A 122.440(2) . . ? C16A C15A H15A 118.8 . . ? C14A C15A H15A 118.8 . . ? C15A C16A C11A 117.992(1) . . ? C15A C16A H16A 121.0 . . ? C11A C16A H16A 121.0 . . ? C7A C17A C14A 126.857(3) . . ? C7A C17A H17A 116.6 . . ? C14A C17A H17A 116.6 . . ? O2B N1B O1B 123.110(2) . . ? O2F N1F O1F 123.120(2) . . ? O2F N1F C1B 122.846(3) . . ? O1F N1F C1B 113.887(3) . . ? N1F C1B C2B 114.287(3) . . ? N1F C1B C6B 123.941(2) . . ? C2B C1B C6B 121.686(2) . . ? C3B C2B C1B 118.983(3) . . ? C3B C2B H2B 120.5 . . ? C1B C2B H2B 120.5 . . ? C2B C3B C4B 121.851(2) . . ? C2B C3B H3B 119.1 . . ? C4B C3B H3B 119.1 . . ? C5B C4B C3B 117.046(2) . . ? C5B C4B C7B 119.470(2) . . ? C3B C4B C7B 123.483(1) . . ? C6B C5B C4B 122.464(3) . . ? C6B C5B H5B 118.8 . . ? C4B C5B H5B 118.8 . . ? C5B C6B C1B 117.961(2) . . ? C5B C6B H6B 121.0 . . ? C1B C6B H6B 121.0 . . ? C17B C7B C4B 126.824(2) . . ? C17B C7B H7B 116.6 . . ? C4B C7B H7B 116.6 . . ? C12B C11B C16B 121.669(1) . . ? C12B C11B Cl1F 124.022(2) . . ? C16B C11B Cl1F 114.309(2) . . ? C13B C12B C11B 119.009(3) . . ? C13B C12B H12B 120.5 . . ? C11B C12B H12B 120.5 . . ? C12B C13B C14B 121.835(1) . . ? C12B C13B H13B 119.1 . . ? C14B C13B H13B 119.1 . . ? C15B C14B C13B 117.044(1) . . ? C15B C14B C17B 119.510(3) . . ? C13B C14B C17B 123.445(2) . . ? C16B C15B C14B 122.440(3) . . ? C16B C15B H15B 118.8 . . ? C14B C15B H15B 118.8 . . ? C15B C16B C11B 117.992(2) . . ? C15B C16B H16B 121.0 . . ? C11B C16B H16B 121.0 . . ? C7B C17B C14B 126.857(2) . . ? C7B C17B H17B 116.6 . . ? C14B C17B H17B 116.6 . . ? O2C N1C O1C 123.138(1) . . ? O2G N1G O1G 123.094(2) . . ? O2G N1G C1C 122.831(2) . . ? O1G N1G C1C 113.926(3) . . ? N1G C1C C2C 114.316(3) . . ? N1G C1C C6C 123.929(2) . . ? C2C C1C C6C 121.669(1) . . ? C3C C2C C1C 119.007(3) . . ? C3C C2C H2C 120.5 . . ? C1C C2C H2C 120.5 . . ? C2C C3C C4C 121.841(2) . . ? C2C C3C H3C 119.1 . . ? C4C C3C H3C 119.1 . . ? C5C C4C C3C 117.040(1) . . ? C5C C4C C7C 119.516(3) . . ? C3C C4C C7C 123.443(1) . . ? C6C C5C C4C 122.440(3) . . ? C6C C5C H5C 118.8 . . ? C4C C5C H5C 118.8 . . ? C5C C6C C1C 117.992(2) . . ? C5C C6C H6C 121.0 . . ? C1C C6C H6C 121.0 . . ? C17C C7C C4C 126.844(3) . . ? C17C C7C H7C 116.6 . . ? C4C C7C H7C 116.6 . . ? C12C C11C C16C 121.691(2) . . ? C12C C11C Cl1G 124.006(3) . . ? C16C C11C Cl1G 114.302(2) . . ? C13C C12C C11C 118.974(3) . . ? C13C C12C H12C 120.5 . . ? C11C C12C H12C 120.5 . . ? C12C C13C C14C 121.848(2) . . ? C12C C13C H13C 119.1 . . ? C14C C13C H13C 119.1 . . ? C15C C14C C13C 117.1 . . ? C15C C14C C17C 119.488(3) . . ? C13C C14C C17C 123.458(2) . . ? C16C C15C C14C 122.448(2) . . ? C16C C15C H15C 118.8 . . ? C14C C15C H15C 118.8 . . ? C15C C16C C11C 117.976(2) . . ? C15C C16C H16C 121.0 . . ? C11C C16C H16C 121.0 . . ? C7C C17C C14C 126.826(3) . . ? C7C C17C H17C 116.6 . . ? C14C C17C H17C 116.6 . . ? O2D N1D O1D 123.138(1) . . ? O2H N1H O1H 123.094(2) . . ? O2H N1H C1D 122.831(2) . . ? O1H N1H C1D 113.926(3) . . ? N1H C1D C2D 114.316(3) . . ? N1H C1D C6D 123.929(1) . . ? C2D C1D C6D 121.669(1) . . ? C3D C2D C1D 119.007(2) . . ? C3D C2D H2D 120.5 . . ? C1D C2D H2D 120.5 . . ? C2D C3D C4D 121.841(1) . . ? C2D C3D H3D 119.1 . . ? C4D C3D H3D 119.1 . . ? C5D C4D C3D 117.040(2) . . ? C5D C4D C7D 119.516(3) . . ? C3D C4D C7D 123.443(2) . . ? C6D C5D C4D 122.440(3) . . ? C6D C5D H5D 118.8 . . ? C4D C5D H5D 118.8 . . ? C5D C6D C1D 117.992(2) . . ? C5D C6D H6D 121.0 . . ? C1D C6D H6D 121.0 . . ? C17D C7D C4D 126.844(3) . . ? C17D C7D H7D 116.6 . . ? C4D C7D H7D 116.6 . . ? C12D C11D C16D 121.692(2) . . ? C12D C11D Cl1H 124.006(3) . . ? C16D C11D Cl1H 114.302(2) . . ? C13D C12D C11D 118.974(3) . . ? C13D C12D H12D 120.5 . . ? C11D C12D H12D 120.5 . . ? C12D C13D C14D 121.848(2) . . ? C12D C13D H13D 119.1 . . ? C14D C13D H13D 119.1 . . ? C15D C14D C13D 117.053(1) . . ? C15D C14D C17D 119.488(3) . . ? C13D C14D C17D 123.458(2) . . ? C16D C15D C14D 122.448(3) . . ? C16D C15D H15D 118.8 . . ? C14D C15D H15D 118.8 . . ? C15D C16D C11D 117.976(2) . . ? C15D C16D H16D 121.0 . . ? C11D C16D H16D 121.0 . . ? C7D C17D C14D 126.826(3) . . ? C7D C17D H17D 116.6 . . ? C14D C17D H17D 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2E N1E C1A C2A -1.4 . . . . ? O1E N1E C1A C2A -177.1 . . . . ? O2E N1E C1A C6A -178.1 . . . . ? O1E N1E C1A C6A 6.2 . . . . ? N1E C1A C2A C3A -177.7 . . . . ? C6A C1A C2A C3A -1.0 . . . . ? C1A C2A C3A C4A 0.9 . . . . ? C2A C3A C4A C5A -0.7 . . . . ? C2A C3A C4A C7A 179.7 . . . . ? C3A C4A C5A C6A 0.6 . . . . ? C7A C4A C5A C6A -179.7 . . . . ? C4A C5A C6A C1A -0.769(1) . . . . ? N1E C1A C6A C5A 177.4 . . . . ? C2A C1A C6A C5A 0.9 . . . . ? C5A C4A C7A C17A 175.9 . . . . ? C3A C4A C7A C17A -4.5 . . . . ? C16A C11A C12A C13A 0.983(1) . . . . ? Cl1E C11A C12A C13A -179.0 . . . . ? C11A C12A C13A C14A -0.9 . . . . ? C12A C13A C14A C15A 0.7 . . . . ? C12A C13A C14A C17A -179.7 . . . . ? C13A C14A C15A C16A -0.6 . . . . ? C17A C14A C15A C16A 179.8 . . . . ? C14A C15A C16A C11A 0.7 . . . . ? C12A C11A C16A C15A -0.9 . . . . ? Cl1E C11A C16A C15A 179.1 . . . . ? C4A C7A C17A C14A 180.0 . . . . ? C15A C14A C17A C7A -175.9 . . . . ? C13A C14A C17A C7A 4.6 . . . . ? O2F N1F C1B C2B -1.432(1) . . . . ? O1F N1F C1B C2B -177.1 . . . . ? O2F N1F C1B C6B -178.1 . . . . ? O1F N1F C1B C6B 6.205(1) . . . . ? N1F C1B C2B C3B -177.7 . . . . ? C6B C1B C2B C3B -1.0 . . . . ? C1B C2B C3B C4B 0.9 . . . . ? C2B C3B C4B C5B -0.7 . . . . ? C2B C3B C4B C7B 179.7 . . . . ? C3B C4B C5B C6B 0.6 . . . . ? C7B C4B C5B C6B -179.7 . . . . ? C4B C5B C6B C1B -0.769(1) . . . . ? N1F C1B C6B C5B 177.4 . . . . ? C2B C1B C6B C5B 0.934(1) . . . . ? C5B C4B C7B C17B 175.9 . . . . ? C3B C4B C7B C17B -4.5 . . . . ? C16B C11B C12B C13B 1.0 . . . . ? Cl1F C11B C12B C13B -179.0 . . . . ? C11B C12B C13B C14B -0.9 . . . . ? C12B C13B C14B C15B 0.7 . . . . ? C12B C13B C14B C17B -179.7 . . . . ? C13B C14B C15B C16B -0.6 . . . . ? C17B C14B C15B C16B 179.8 . . . . ? C14B C15B C16B C11B 0.7 . . . . ? C12B C11B C16B C15B -0.9 . . . . ? Cl1F C11B C16B C15B 179.1 . . . . ? C4B C7B C17B C14B 180.0 . . . . ? C15B C14B C17B C7B -175.9 . . . . ? C13B C14B C17B C7B 4.6 . . . . ? O2G N1G C1C C2C -1.5 . . . . ? O1G N1G C1C C2C -177.1 . . . . ? O2G N1G C1C C6C -178.1 . . . . ? O1G N1G C1C C6C 6.208(1) . . . . ? N1G C1C C2C C3C -177.7 . . . . ? C6C C1C C2C C3C -1.0 . . . . ? C1C C2C C3C C4C 0.9 . . . . ? C2C C3C C4C C5C -0.7 . . . . ? C2C C3C C4C C7C 179.7 . . . . ? C3C C4C C5C C6C 0.6 . . . . ? C7C C4C C5C C6C -179.8 . . . . ? C4C C5C C6C C1C -0.7 . . . . ? N1G C1C C6C C5C 177.336(1) . . . . ? C2C C1C C6C C5C 0.9 . . . . ? C5C C4C C7C C17C 175.9 . . . . ? C3C C4C C7C C17C -4.6 . . . . ? C16C C11C C12C C13C 1.0 . . . . ? Cl1G C11C C12C C13C -179.0 . . . . ? C11C C12C C13C C14C -0.9 . . . . ? C12C C13C C14C C15C 0.678(2) . . . . ? C12C C13C C14C C17C -179.7 . . . . ? C13C C14C C15C C16C -0.6 . . . . ? C17C C14C C15C C16C 179.7 . . . . ? C14C C15C C16C C11C 0.765(1) . . . . ? C12C C11C C16C C15C -0.9 . . . . ? Cl1G C11C C16C C15C 179.0 . . . . ? C4C C7C C17C C14C -180.0 . . . . ? C15C C14C C17C C7C -175.9 . . . . ? C13C C14C C17C C7C 4.5 . . . . ? O2H N1H C1D C2D -1.5 . . . . ? O1H N1H C1D C2D -177.1 . . . . ? O2H N1H C1D C6D -178.1 . . . . ? O1H N1H C1D C6D 6.2 . . . . ? N1H C1D C2D C3D -177.7 . . . . ? C6D C1D C2D C3D -1.0 . . . . ? C1D C2D C3D C4D 0.878(1) . . . . ? C2D C3D C4D C5D -0.7 . . . . ? C2D C3D C4D C7D 179.7 . . . . ? C3D C4D C5D C6D 0.635(1) . . . . ? C7D C4D C5D C6D -179.8 . . . . ? C4D C5D C6D C1D -0.741(1) . . . . ? N1H C1D C6D C5D 177.3 . . . . ? C2D C1D C6D C5D 0.9 . . . . ? C5D C4D C7D C17D 175.9 . . . . ? C3D C4D C7D C17D -4.6 . . . . ? C16D C11D C12D C13D 1.0 . . . . ? Cl1H C11D C12D C13D -179.0 . . . . ? C11D C12D C13D C14D -0.9 . . . . ? C12D C13D C14D C15D 0.678(1) . . . . ? C12D C13D C14D C17D -179.7 . . . . ? C13D C14D C15D C16D -0.6 . . . . ? C17D C14D C15D C16D 179.731(1) . . . . ? C14D C15D C16D C11D 0.765(1) . . . . ? C12D C11D C16D C15D -0.932(1) . . . . ? Cl1H C11D C16D C15D 179.0 . . . . ? C4D C7D C17D C14D -180.0 . . . . ? C15D C14D C17D C7D -175.9 . . . . ? C13D C14D C17D C7D 4.5 . . . . ? _diffrn_measured_fraction_theta_max 0.485 _diffrn_reflns_theta_full 27.82 _diffrn_measured_fraction_theta_full 0.485 _refine_diff_density_max 0.175 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.036 # start Validation Reply Form _vrf_REFLT03_CNS-TolI-big-A1 ; PROBLEM: Reflection count < 85% complete (theta max?) RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. The measurement was performed in a hemisphere strategy. ; _vrf_SYMMG01_CNS-TolI-big-A1 ; PROBLEM: Unrecognised _symmetry_space_group_name_H-M RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. ; _vrf_SYMMG02_CNS-TolI-big-A1 ; PROBLEM: Supplied _symmetry_space_group_name_H-M not recognised RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. ; _vrf_PLAT029_CNS-TolI-big-A1 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.49 RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. The measurement was performed in a hemisphere strategy. ; # end Validation Reply Form #===END data_CNS-TolII-small-P21_c _database_code_depnum_ccdc_archive 'CCDC 761213' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9239(2) _cell_length_b 12.9733(6) _cell_length_c 12.2398(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.192(2) _cell_angle_gamma 90.00 _cell_volume 622.11(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3468 _cell_measurement_theta_min 3.1405 _cell_measurement_theta_max 24.1575 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.721818 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3445 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.73 _reflns_number_total 2455 _reflns_number_gt 1478 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+0.1584P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2455 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1572 _refine_ls_wR_factor_gt 0.1454 _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_restrained_S_all 1.217 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3694(12) -0.46063(14) -0.1747(4) 0.1141(16) Uani 0.50 1 d P . . N11 N 0.363(3) -0.4162(6) -0.1733(9) 0.085(2) Uani 0.50 1 d P . . O11 O 0.3133(19) -0.4976(5) -0.1223(5) 0.132(2) Uani 0.50 1 d P . . O12 O 0.5003(10) -0.4123(3) -0.2577(3) 0.1160(12) Uani 0.50 1 d P . . C1 C 0.2607(5) -0.32908(16) -0.12271(17) 0.0723(5) Uani 1 1 d . . . C2 C 0.3153(5) -0.23931(18) -0.17879(16) 0.0809(6) Uani 1 1 d . . . H2A H 0.4138 -0.2410 -0.2462 0.097 Uiso 1 1 calc R . . C3 C 0.2227(5) -0.14725(16) -0.13410(16) 0.0758(6) Uani 1 1 d . . . H3A H 0.2570 -0.0864 -0.1721 0.091 Uiso 1 1 calc R . . C4 C 0.0782(4) -0.14343(14) -0.03272(15) 0.0655(5) Uani 1 1 d . . . C5 C 0.0282(5) -0.23610(15) 0.02081(16) 0.0726(5) Uani 1 1 d . . . H5A H -0.0697 -0.2351 0.0883 0.087 Uiso 1 1 calc R . . C6 C 0.1192(5) -0.32967(15) -0.02287(17) 0.0775(6) Uani 1 1 d . . . H6A H 0.0855 -0.3910 0.0143 0.093 Uiso 1 1 calc R . . C7 C -0.0240(5) -0.04634(13) 0.01835(16) 0.0736(5) Uani 1 1 d . . . H7A H -0.1341 -0.0518 0.0835 0.088 Uiso 1 1 calc R . . Cl11 Cl -0.3694(12) 0.46063(14) 0.1747(4) 0.1141(16) Uani 0.50 1 d P . . N1 N -0.363(3) 0.4162(6) 0.1733(9) 0.085(2) Uani 0.50 1 d P . . O1 O -0.3133(19) 0.4976(5) 0.1223(5) 0.132(2) Uani 0.50 1 d P . . O2 O -0.5003(10) 0.4123(3) 0.2577(3) 0.1160(12) Uani 0.50 1 d P . . C11 C -0.2607(5) 0.32908(16) 0.12271(17) 0.0723(5) Uani 1 1 d . . . C12 C -0.3153(5) 0.23931(18) 0.17879(16) 0.0809(6) Uani 1 1 d . . . H12A H -0.4138 0.2410 0.2462 0.097 Uiso 1 1 calc R . . C13 C -0.2227(5) 0.14725(16) 0.13410(16) 0.0758(6) Uani 1 1 d . . . H13A H -0.2570 0.0864 0.1721 0.091 Uiso 1 1 calc R . . C14 C -0.0782(4) 0.14343(14) 0.03272(15) 0.0655(5) Uani 1 1 d . . . C15 C -0.0282(5) 0.23610(15) -0.02081(16) 0.0726(5) Uani 1 1 d . . . H15A H 0.0697 0.2351 -0.0883 0.087 Uiso 1 1 calc R . . C16 C -0.1192(5) 0.32967(15) 0.02287(17) 0.0775(6) Uani 1 1 d . . . H16A H -0.0855 0.3910 -0.0143 0.093 Uiso 1 1 calc R . . C17 C 0.0240(5) 0.04634(13) -0.01835(16) 0.0736(5) Uani 1 1 d . . . H17A H 0.1341 0.0518 -0.0835 0.088 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1151(15) 0.094(3) 0.133(3) -0.045(3) 0.0060(17) 0.023(2) N11 0.079(3) 0.073(5) 0.102(5) 0.004(5) -0.004(3) 0.004(4) O11 0.179(5) 0.071(3) 0.151(5) 0.005(3) 0.040(4) 0.017(3) O12 0.151(3) 0.095(2) 0.104(3) -0.030(2) 0.030(2) 0.021(2) C1 0.0592(11) 0.0817(14) 0.0754(13) -0.0176(11) -0.0023(9) 0.0049(10) C2 0.0711(13) 0.1054(16) 0.0667(13) -0.0023(12) 0.0089(10) -0.0007(12) C3 0.0716(13) 0.0814(13) 0.0750(13) 0.0064(11) 0.0085(10) -0.0026(10) C4 0.0526(10) 0.0769(12) 0.0667(12) -0.0043(10) -0.0003(9) 0.0002(9) C5 0.0719(12) 0.0818(13) 0.0645(11) 0.0018(10) 0.0074(9) -0.0014(10) C6 0.0745(13) 0.0785(14) 0.0796(14) 0.0026(11) 0.0040(11) 0.0043(10) C7 0.0625(11) 0.0858(13) 0.0728(12) 0.0053(10) 0.0060(9) -0.0037(11) Cl11 0.1151(15) 0.094(3) 0.133(3) -0.045(3) 0.0060(17) 0.023(2) N1 0.079(3) 0.073(5) 0.102(5) 0.004(5) -0.004(3) 0.004(4) O1 0.179(5) 0.071(3) 0.151(5) 0.005(3) 0.040(4) 0.017(3) O2 0.151(3) 0.095(2) 0.104(3) -0.030(2) 0.030(2) 0.021(2) C11 0.0592(11) 0.0817(14) 0.0754(13) -0.0176(11) -0.0023(9) 0.0049(10) C12 0.0711(13) 0.1054(16) 0.0667(13) -0.0023(12) 0.0089(10) -0.0007(12) C13 0.0716(13) 0.0814(13) 0.0750(13) 0.0064(11) 0.0085(10) -0.0026(10) C14 0.0526(10) 0.0769(12) 0.0667(12) -0.0043(10) -0.0003(9) 0.0002(9) C15 0.0719(12) 0.0818(13) 0.0645(11) 0.0018(10) 0.0074(9) -0.0014(10) C16 0.0745(13) 0.0785(14) 0.0796(14) 0.0026(11) 0.0040(11) 0.0043(10) C17 0.0625(11) 0.0858(13) 0.0728(12) 0.0053(10) 0.0060(9) -0.0037(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.577(7) . ? Cl1 O11 0.839(5) . ? Cl1 O12 1.321(6) . ? Cl1 C1 1.879(3) . ? N11 O12 1.191(12) . ? N11 O11 1.247(14) . ? N11 C1 1.361(7) . ? C1 C6 1.370(3) . ? C1 C2 1.375(3) . ? C2 C3 1.371(3) . ? C2 H2A 0.9300 . ? C3 C4 1.394(3) . ? C3 H3A 0.9300 . ? C4 C5 1.388(2) . ? C4 C7 1.472(2) . ? C5 C6 1.381(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.301(3) . ? C7 H7A 0.9300 . ? Cl11 N1 0.577(7) . ? Cl11 O1 0.839(5) . ? Cl11 O2 1.321(6) . ? Cl11 C11 1.879(3) . ? N1 O2 1.191(12) . ? N1 O1 1.247(14) . ? N1 C11 1.361(7) . ? C11 C16 1.370(3) . ? C11 C12 1.375(3) . ? C12 C13 1.371(3) . ? C12 H12A 0.9300 . ? C13 C14 1.394(3) . ? C13 H13A 0.9300 . ? C14 C15 1.388(2) . ? C14 C17 1.472(2) . ? C15 C16 1.381(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 122(2) . . ? N11 Cl1 O12 64.4(16) . . ? O11 Cl1 O12 170.8(7) . . ? N11 Cl1 C1 21.9(15) . . ? O11 Cl1 C1 100.7(7) . . ? O12 Cl1 C1 86.3(2) . . ? Cl1 N11 O12 89.7(15) . . ? Cl1 N11 O11 34.7(14) . . ? O12 N11 O11 124.1(6) . . ? Cl1 N11 C1 149(2) . . ? O12 N11 C1 121.3(8) . . ? O11 N11 C1 114.6(8) . . ? Cl1 O11 N11 23.0(7) . . ? N11 O12 Cl1 25.9(3) . . ? N11 C1 C6 123.1(5) . . ? N11 C1 C2 114.7(5) . . ? C6 C1 C2 122.2(2) . . ? N11 C1 Cl1 9.1(6) . . ? C6 C1 Cl1 114.1(2) . . ? C2 C1 Cl1 123.8(2) . . ? C3 C2 C1 119.11(19) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.1(2) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C5 C4 C3 117.69(19) . . ? C5 C4 C7 119.45(17) . . ? C3 C4 C7 122.86(19) . . ? C6 C5 C4 122.14(19) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C1 C6 C5 117.8(2) . . ? C1 C6 H6A 121.1 . . ? C5 C6 H6A 121.1 . . ? C17 C7 C4 126.6(3) . . ? C17 C7 H7A 116.7 . . ? C4 C7 H7A 116.7 . . ? N1 Cl11 O1 122(2) . . ? N1 Cl11 O2 64.4(16) . . ? O1 Cl11 O2 170.8(7) . . ? N1 Cl11 C11 21.9(15) . . ? O1 Cl11 C11 100.7(7) . . ? O2 Cl11 C11 86.3(2) . . ? Cl11 N1 O2 89.7(15) . . ? Cl11 N1 O1 34.7(14) . . ? O2 N1 O1 124.1(6) . . ? Cl11 N1 C11 149(2) . . ? O2 N1 C11 121.3(8) . . ? O1 N1 C11 114.6(8) . . ? Cl11 O1 N1 23.0(7) . . ? N1 O2 Cl11 25.9(3) . . ? N1 C11 C16 123.1(5) . . ? N1 C11 C12 114.7(5) . . ? C16 C11 C12 122.2(2) . . ? N1 C11 Cl11 9.1(6) . . ? C16 C11 Cl11 114.1(2) . . ? C12 C11 Cl11 123.8(2) . . ? C13 C12 C11 119.11(19) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 121.1(2) . . ? C12 C13 H13A 119.5 . . ? C14 C13 H13A 119.5 . . ? C15 C14 C13 117.69(19) . . ? C15 C14 C17 119.45(17) . . ? C13 C14 C17 122.86(19) . . ? C16 C15 C14 122.14(19) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C11 C16 C15 117.8(2) . . ? C11 C16 H16A 121.1 . . ? C15 C16 H16A 121.1 . . ? C7 C17 C14 126.6(3) . . ? C7 C17 H17A 116.7 . . ? C14 C17 H17A 116.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.9(10) . . . . ? C1 Cl1 N11 O12 -176(4) . . . . ? O12 Cl1 N11 O11 -172.9(10) . . . . ? C1 Cl1 N11 O11 11(4) . . . . ? O11 Cl1 N11 C1 -11(4) . . . . ? O12 Cl1 N11 C1 176(4) . . . . ? O12 Cl1 O11 N11 135(6) . . . . ? C1 Cl1 O11 N11 -4.1(17) . . . . ? O12 N11 O11 Cl1 -8.6(12) . . . . ? C1 N11 O11 Cl1 174(2) . . . . ? O11 N11 O12 Cl1 4.9(7) . . . . ? C1 N11 O12 Cl1 -178(2) . . . . ? O11 Cl1 O12 N11 -139(5) . . . . ? C1 Cl1 O12 N11 1.3(14) . . . . ? Cl1 N11 C1 C6 8(4) . . . . ? O12 N11 C1 C6 -176.4(6) . . . . ? O11 N11 C1 C6 1.1(12) . . . . ? Cl1 N11 C1 C2 -173(3) . . . . ? O12 N11 C1 C2 2.5(11) . . . . ? O11 N11 C1 C2 -179.9(7) . . . . ? O12 N11 C1 Cl1 176(4) . . . . ? O11 N11 C1 Cl1 -7(3) . . . . ? O11 Cl1 C1 N11 171(4) . . . . ? O12 Cl1 C1 N11 -3(3) . . . . ? N11 Cl1 C1 C6 -173(3) . . . . ? O11 Cl1 C1 C6 -2.0(7) . . . . ? O12 Cl1 C1 C6 -176.1(2) . . . . ? N11 Cl1 C1 C2 7(4) . . . . ? O11 Cl1 C1 C2 178.2(6) . . . . ? O12 Cl1 C1 C2 4.1(4) . . . . ? N11 C1 C2 C3 -179.5(5) . . . . ? C6 C1 C2 C3 -0.6(3) . . . . ? Cl1 C1 C2 C3 179.2(2) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C2 C3 C4 C7 179.84(18) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C7 C4 C5 C6 -179.92(17) . . . . ? N11 C1 C6 C5 179.3(5) . . . . ? C2 C1 C6 C5 0.5(3) . . . . ? Cl1 C1 C6 C5 -179.3(2) . . . . ? C4 C5 C6 C1 -0.5(3) . . . . ? C5 C4 C7 C17 175.7(2) . . . . ? C3 C4 C7 C17 -4.7(4) . . . . ? O1 Cl11 N1 O2 -172.9(10) . . . . ? C11 Cl11 N1 O2 176(4) . . . . ? O2 Cl11 N1 O1 172.9(10) . . . . ? C11 Cl11 N1 O1 -11(4) . . . . ? O1 Cl11 N1 C11 11(4) . . . . ? O2 Cl11 N1 C11 -176(4) . . . . ? O2 Cl11 O1 N1 -135(6) . . . . ? C11 Cl11 O1 N1 4.1(17) . . . . ? O2 N1 O1 Cl11 8.6(12) . . . . ? C11 N1 O1 Cl11 -174(2) . . . . ? O1 N1 O2 Cl11 -4.9(7) . . . . ? C11 N1 O2 Cl11 178(2) . . . . ? O1 Cl11 O2 N1 139(5) . . . . ? C11 Cl11 O2 N1 -1.3(14) . . . . ? Cl11 N1 C11 C16 -8(4) . . . . ? O2 N1 C11 C16 176.4(6) . . . . ? O1 N1 C11 C16 -1.1(12) . . . . ? Cl11 N1 C11 C12 173(3) . . . . ? O2 N1 C11 C12 -2.5(11) . . . . ? O1 N1 C11 C12 179.9(7) . . . . ? O2 N1 C11 Cl11 -176(4) . . . . ? O1 N1 C11 Cl11 7(3) . . . . ? O1 Cl11 C11 N1 -171(4) . . . . ? O2 Cl11 C11 N1 3(3) . . . . ? N1 Cl11 C11 C16 173(3) . . . . ? O1 Cl11 C11 C16 2.0(7) . . . . ? O2 Cl11 C11 C16 176.1(2) . . . . ? N1 Cl11 C11 C12 -7(4) . . . . ? O1 Cl11 C11 C12 -178.2(6) . . . . ? O2 Cl11 C11 C12 -4.1(4) . . . . ? N1 C11 C12 C13 179.5(5) . . . . ? C16 C11 C12 C13 0.6(3) . . . . ? Cl11 C11 C12 C13 -179.2(2) . . . . ? C11 C12 C13 C14 -0.7(3) . . . . ? C12 C13 C14 C15 0.6(3) . . . . ? C12 C13 C14 C17 -179.84(18) . . . . ? C13 C14 C15 C16 -0.5(3) . . . . ? C17 C14 C15 C16 179.92(17) . . . . ? N1 C11 C16 C15 -179.3(5) . . . . ? C12 C11 C16 C15 -0.5(3) . . . . ? Cl11 C11 C16 C15 179.3(2) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.7(2) . . . . ? C13 C14 C17 C7 4.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 27.73 _diffrn_measured_fraction_theta_full 0.880 _refine_diff_density_max 0.093 _refine_diff_density_min -0.113 _refine_diff_density_rms 0.028 # start Validation Reply Form _vrf_SYMMG02_CNS-TolII-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-TolII-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.88 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; # end Validation Reply Form #===END data_CNS-TolII-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761214' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9239(2) _cell_length_b 12.9733(6) _cell_length_c 12.2398(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.192(2) _cell_angle_gamma 90.00 _cell_volume 622.11(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3468 _cell_measurement_theta_min 3.1405 _cell_measurement_theta_max 24.1575 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.721818 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3445 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.73 _reflns_number_total 2455 _reflns_number_gt 1478 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+0.1584P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(2) _refine_ls_number_reflns 2455 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3689(8) -0.46046(12) -0.1754(3) 0.1134(11) Uani 0.403(2) 1 d P . . N11 N 0.367(2) -0.4160(4) -0.1722(6) 0.0859(15) Uani 0.597(2) 1 d P . . O11 O 0.3129(14) -0.4971(3) -0.1231(4) 0.1291(18) Uani 0.597(2) 1 d P . . O12 O 0.5007(8) -0.4131(2) -0.2578(2) 0.1136(10) Uani 0.597(2) 1 d P . . C1 C 0.2612(4) -0.32914(13) -0.12285(14) 0.0725(5) Uani 1 1 d . . . C2 C 0.3155(4) -0.23910(15) -0.17913(13) 0.0804(5) Uani 1 1 d . . . H2A H 0.4136 -0.2406 -0.2466 0.097 Uiso 1 1 calc R . . C3 C 0.2224(4) -0.14752(13) -0.13398(13) 0.0766(5) Uani 1 1 d . . . H3A H 0.2563 -0.0866 -0.1719 0.092 Uiso 1 1 calc R . . C4 C 0.0784(4) -0.14332(12) -0.03292(12) 0.0652(4) Uani 1 1 d . . . C5 C 0.0284(4) -0.23606(12) 0.02091(13) 0.0729(5) Uani 1 1 d . . . H5A H -0.0694 -0.2351 0.0884 0.087 Uiso 1 1 calc R . . C6 C 0.1195(4) -0.32930(12) -0.02277(14) 0.0768(5) Uani 1 1 d . . . H6A H 0.0859 -0.3906 0.0145 0.092 Uiso 1 1 calc R . . C7 C -0.0237(4) -0.04645(11) 0.01823(14) 0.0724(4) Uani 1 1 d . . . H7A H -0.1336 -0.0521 0.0834 0.087 Uiso 1 1 calc R . . Cl11 Cl -0.3689(8) 0.46046(12) 0.1754(3) 0.1134(11) Uani 0.597(2) 1 d P . . N1 N -0.367(2) 0.4160(4) 0.1722(6) 0.0859(15) Uani 0.403(2) 1 d P . . O1 O -0.3129(14) 0.4971(3) 0.1231(4) 0.1291(18) Uani 0.403(2) 1 d P . . O2 O -0.5007(8) 0.4131(2) 0.2578(2) 0.1136(10) Uani 0.403(2) 1 d P . . C11 C -0.2612(4) 0.32914(13) 0.12285(14) 0.0725(5) Uani 1 1 d . . . C12 C -0.3155(4) 0.23910(15) 0.17913(13) 0.0804(5) Uani 1 1 d . . . H12A H -0.4136 0.2406 0.2466 0.097 Uiso 1 1 calc R . . C13 C -0.2224(4) 0.14752(13) 0.13398(13) 0.0766(5) Uani 1 1 d . . . H13A H -0.2563 0.0866 0.1719 0.092 Uiso 1 1 calc R . . C14 C -0.0784(4) 0.14332(12) 0.03292(12) 0.0652(4) Uani 1 1 d . . . C15 C -0.0284(4) 0.23606(12) -0.02091(13) 0.0729(5) Uani 1 1 d . . . H15A H 0.0694 0.2351 -0.0884 0.087 Uiso 1 1 calc R . . C16 C -0.1195(4) 0.32930(12) 0.02277(14) 0.0768(5) Uani 1 1 d . . . H16A H -0.0859 0.3906 -0.0145 0.092 Uiso 1 1 calc R . . C17 C 0.0237(4) 0.04645(11) -0.01823(14) 0.0724(4) Uani 1 1 d . . . H17A H 0.1336 0.0521 -0.0834 0.087 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1130(12) 0.094(2) 0.1334(19) -0.046(2) 0.0072(12) 0.0203(17) N11 0.083(3) 0.070(4) 0.104(4) -0.002(3) -0.009(3) 0.001(3) O11 0.170(4) 0.074(2) 0.147(4) 0.007(2) 0.042(3) 0.016(2) O12 0.153(3) 0.0915(19) 0.100(2) -0.0258(17) 0.0345(19) 0.0185(18) C1 0.0585(9) 0.0829(12) 0.0755(11) -0.0168(9) -0.0027(8) 0.0045(8) C2 0.0701(11) 0.1058(14) 0.0660(10) -0.0027(10) 0.0099(8) 0.0000(10) C3 0.0707(10) 0.0833(11) 0.0763(11) 0.0074(9) 0.0071(9) -0.0035(9) C4 0.0522(8) 0.0785(10) 0.0645(10) -0.0044(8) 0.0004(7) 0.0005(7) C5 0.0708(10) 0.0837(11) 0.0647(9) 0.0024(9) 0.0079(8) -0.0013(9) C6 0.0747(11) 0.0773(11) 0.0783(12) 0.0024(9) 0.0045(9) 0.0029(9) C7 0.0623(9) 0.0831(11) 0.0721(10) 0.0043(9) 0.0056(8) -0.0034(9) Cl11 0.1130(12) 0.094(2) 0.1334(19) -0.046(2) 0.0072(12) 0.0203(17) N1 0.083(3) 0.070(4) 0.104(4) -0.002(3) -0.009(3) 0.001(3) O1 0.170(4) 0.074(2) 0.147(4) 0.007(2) 0.042(3) 0.016(2) O2 0.153(3) 0.0915(19) 0.100(2) -0.0258(17) 0.0345(19) 0.0185(18) C11 0.0585(9) 0.0829(12) 0.0755(11) -0.0168(9) -0.0027(8) 0.0045(8) C12 0.0701(11) 0.1058(14) 0.0660(10) -0.0027(10) 0.0099(8) 0.0000(10) C13 0.0707(10) 0.0833(11) 0.0763(11) 0.0074(9) 0.0071(9) -0.0035(9) C14 0.0522(8) 0.0785(10) 0.0645(10) -0.0044(8) 0.0004(7) 0.0005(7) C15 0.0708(10) 0.0837(11) 0.0647(9) 0.0024(9) 0.0079(8) -0.0013(9) C16 0.0747(11) 0.0773(11) 0.0783(12) 0.0024(9) 0.0045(9) 0.0029(9) C17 0.0623(9) 0.0831(11) 0.0721(10) 0.0043(9) 0.0056(8) -0.0034(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.578(5) . ? Cl1 O11 0.836(4) . ? Cl1 O12 1.311(4) . ? Cl1 C1 1.877(2) . ? N11 O12 1.198(8) . ? N11 O11 1.236(9) . ? N11 C1 1.354(5) . ? C1 C6 1.373(2) . ? C1 C2 1.379(2) . ? C2 C3 1.369(2) . ? C2 H2A 0.9300 . ? C3 C4 1.389(2) . ? C3 H3A 0.9300 . ? C4 C5 1.391(2) . ? C4 C7 1.470(2) . ? C5 C6 1.378(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.302(3) . ? C7 H7A 0.9300 . ? Cl11 N1 0.578(5) . ? Cl11 O1 0.836(4) . ? Cl11 O2 1.311(4) . ? Cl11 C11 1.877(2) . ? N1 O2 1.198(8) . ? N1 O1 1.236(9) . ? N1 C11 1.354(5) . ? C11 C16 1.373(2) . ? C11 C12 1.379(2) . ? C12 C13 1.369(2) . ? C12 H12A 0.9300 . ? C13 C14 1.389(2) . ? C13 H13A 0.9300 . ? C14 C15 1.391(2) . ? C14 C17 1.470(2) . ? C15 C16 1.378(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 120.7(13) . . ? N11 Cl1 O12 65.9(10) . . ? O11 Cl1 O12 170.5(5) . . ? N11 Cl1 C1 21.1(10) . . ? O11 Cl1 C1 100.4(5) . . ? O12 Cl1 C1 86.81(17) . . ? Cl1 N11 O12 87.9(10) . . ? Cl1 N11 O11 35.6(9) . . ? O12 N11 O11 123.1(5) . . ? Cl1 N11 C1 150.0(14) . . ? O12 N11 C1 121.6(6) . . ? O11 N11 C1 115.3(6) . . ? Cl1 O11 N11 23.7(4) . . ? N11 O12 Cl1 26.2(2) . . ? N11 C1 C6 123.1(4) . . ? N11 C1 C2 115.0(4) . . ? C6 C1 C2 121.91(16) . . ? N11 C1 Cl1 8.9(4) . . ? C6 C1 Cl1 114.47(18) . . ? C2 C1 Cl1 123.62(17) . . ? C3 C2 C1 118.79(16) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C2 C3 C4 121.64(17) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C5 C4 C3 117.57(16) . . ? C5 C4 C7 119.27(14) . . ? C3 C4 C7 123.15(16) . . ? C6 C5 C4 121.95(15) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C1 C6 C5 118.13(16) . . ? C1 C6 H6A 120.9 . . ? C5 C6 H6A 120.9 . . ? C17 C7 C4 126.7(2) . . ? C17 C7 H7A 116.6 . . ? C4 C7 H7A 116.6 . . ? N1 Cl11 O1 120.7(13) . . ? N1 Cl11 O2 65.9(10) . . ? O1 Cl11 O2 170.5(5) . . ? N1 Cl11 C11 21.1(10) . . ? O1 Cl11 C11 100.4(5) . . ? O2 Cl11 C11 86.81(17) . . ? Cl11 N1 O2 87.9(10) . . ? Cl11 N1 O1 35.6(9) . . ? O2 N1 O1 123.1(5) . . ? Cl11 N1 C11 150.0(14) . . ? O2 N1 C11 121.6(6) . . ? O1 N1 C11 115.3(6) . . ? Cl11 O1 N1 23.7(4) . . ? N1 O2 Cl11 26.2(2) . . ? N1 C11 C16 123.1(4) . . ? N1 C11 C12 115.0(4) . . ? C16 C11 C12 121.91(16) . . ? N1 C11 Cl11 8.9(4) . . ? C16 C11 Cl11 114.47(18) . . ? C12 C11 Cl11 123.62(17) . . ? C13 C12 C11 118.79(16) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? C12 C13 C14 121.64(17) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C15 C14 C13 117.57(16) . . ? C15 C14 C17 119.27(14) . . ? C13 C14 C17 123.15(16) . . ? C16 C15 C14 121.95(15) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C11 C16 C15 118.13(16) . . ? C11 C16 H16A 120.9 . . ? C15 C16 H16A 120.9 . . ? C7 C17 C14 126.7(2) . . ? C7 C17 H17A 116.6 . . ? C14 C17 H17A 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.3(7) . . . . ? C1 Cl1 N11 O12 -170(3) . . . . ? O12 Cl1 N11 O11 -172.3(7) . . . . ? C1 Cl1 N11 O11 17(3) . . . . ? O11 Cl1 N11 C1 -17(3) . . . . ? O12 Cl1 N11 C1 170(3) . . . . ? O12 Cl1 O11 N11 132(4) . . . . ? C1 Cl1 O11 N11 -6.3(12) . . . . ? O12 N11 O11 Cl1 -9.2(9) . . . . ? C1 N11 O11 Cl1 170.5(18) . . . . ? O11 N11 O12 Cl1 5.3(5) . . . . ? C1 N11 O12 Cl1 -174.3(16) . . . . ? O11 Cl1 O12 N11 -136(4) . . . . ? C1 Cl1 O12 N11 3.5(10) . . . . ? Cl1 N11 C1 C6 14(3) . . . . ? O12 N11 C1 C6 -177.3(5) . . . . ? O11 N11 C1 C6 3.1(9) . . . . ? Cl1 N11 C1 C2 -168(3) . . . . ? O12 N11 C1 C2 0.9(8) . . . . ? O11 N11 C1 C2 -178.7(6) . . . . ? O12 N11 C1 Cl1 169(3) . . . . ? O11 N11 C1 Cl1 -11(2) . . . . ? O11 Cl1 C1 N11 165(3) . . . . ? O12 Cl1 C1 N11 -9(3) . . . . ? N11 Cl1 C1 C6 -167(3) . . . . ? O11 Cl1 C1 C6 -2.1(6) . . . . ? O12 Cl1 C1 C6 -175.9(2) . . . . ? N11 Cl1 C1 C2 13(3) . . . . ? O11 Cl1 C1 C2 178.3(5) . . . . ? O12 Cl1 C1 C2 4.6(3) . . . . ? N11 C1 C2 C3 -178.8(4) . . . . ? C6 C1 C2 C3 -0.6(2) . . . . ? Cl1 C1 C2 C3 178.97(18) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C2 C3 C4 C7 179.81(15) . . . . ? C3 C4 C5 C6 0.5(2) . . . . ? C7 C4 C5 C6 -179.86(14) . . . . ? N11 C1 C6 C5 178.5(4) . . . . ? C2 C1 C6 C5 0.5(2) . . . . ? Cl1 C1 C6 C5 -179.08(16) . . . . ? C4 C5 C6 C1 -0.5(2) . . . . ? C5 C4 C7 C17 175.7(2) . . . . ? C3 C4 C7 C17 -4.7(3) . . . . ? O1 Cl11 N1 O2 -172.3(7) . . . . ? C11 Cl11 N1 O2 170(3) . . . . ? O2 Cl11 N1 O1 172.3(7) . . . . ? C11 Cl11 N1 O1 -17(3) . . . . ? O1 Cl11 N1 C11 17(3) . . . . ? O2 Cl11 N1 C11 -170(3) . . . . ? O2 Cl11 O1 N1 -132(4) . . . . ? C11 Cl11 O1 N1 6.3(12) . . . . ? O2 N1 O1 Cl11 9.2(9) . . . . ? C11 N1 O1 Cl11 -170.5(18) . . . . ? O1 N1 O2 Cl11 -5.3(5) . . . . ? C11 N1 O2 Cl11 174.3(16) . . . . ? O1 Cl11 O2 N1 136(4) . . . . ? C11 Cl11 O2 N1 -3.5(10) . . . . ? Cl11 N1 C11 C16 -14(3) . . . . ? O2 N1 C11 C16 177.3(5) . . . . ? O1 N1 C11 C16 -3.1(9) . . . . ? Cl11 N1 C11 C12 168(3) . . . . ? O2 N1 C11 C12 -0.9(8) . . . . ? O1 N1 C11 C12 178.7(6) . . . . ? O2 N1 C11 Cl11 -169(3) . . . . ? O1 N1 C11 Cl11 11(2) . . . . ? O1 Cl11 C11 N1 -165(3) . . . . ? O2 Cl11 C11 N1 9(3) . . . . ? N1 Cl11 C11 C16 167(3) . . . . ? O1 Cl11 C11 C16 2.1(6) . . . . ? O2 Cl11 C11 C16 175.9(2) . . . . ? N1 Cl11 C11 C12 -13(3) . . . . ? O1 Cl11 C11 C12 -178.3(5) . . . . ? O2 Cl11 C11 C12 -4.6(3) . . . . ? N1 C11 C12 C13 178.8(4) . . . . ? C16 C11 C12 C13 0.6(2) . . . . ? Cl11 C11 C12 C13 -178.97(18) . . . . ? C11 C12 C13 C14 -0.6(2) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C12 C13 C14 C17 -179.81(15) . . . . ? C13 C14 C15 C16 -0.5(2) . . . . ? C17 C14 C15 C16 179.86(14) . . . . ? N1 C11 C16 C15 -178.5(4) . . . . ? C12 C11 C16 C15 -0.5(2) . . . . ? Cl11 C11 C16 C15 179.08(16) . . . . ? C14 C15 C16 C11 0.5(2) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.7(2) . . . . ? C13 C14 C17 C7 4.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 27.73 _diffrn_measured_fraction_theta_full 0.917 _refine_diff_density_max 0.101 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.027 # start Validation Reply Form _vrf_SYMMG02_CNS-TolII-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-TolII-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.92 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; # end Validation Reply Form #===END data_CNS-TolII-big-A1 _database_code_depnum_ccdc_archive 'CCDC 761215' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'A 1' _symmetry_space_group_name_Hall 'A 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, y+1/2, z+1/2' _cell_length_a 3.9239(2) _cell_length_b 25.9466(6) _cell_length_c 24.4796(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.192(2) _cell_angle_gamma 90.00 _cell_volume 2488.45(15) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13946 _cell_measurement_theta_min 3.1405 _cell_measurement_theta_max 24.9275 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.784666 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'refined from Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4191 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.78 _reflns_number_total 3431 _reflns_number_gt 2081 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction 'SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0091P)^2^+5.7791P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(3) _refine_ls_number_reflns 3431 _refine_ls_number_parameters 72 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1071 _refine_ls_R_factor_gt 0.0649 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1A Cl 0.3689 -0.2302 -0.0877 0.1126(6) Uani 0.44(2) 1 d P A 1 N1A N -0.3666 0.2080 0.0861 0.0843(12) Uani 0.44(2) 1 d P A 1 O1A O -0.3129 0.2486 0.0616 0.1300(16) Uani 0.44(2) 1 d P A 1 O2A O -0.5007 0.2066 0.1289 0.1129(11) Uani 0.44(2) 1 d P A 1 Cl1E Cl -0.3689 0.2302 0.0877 0.1126(6) Uani 0.56(2) 1 d P A 2 N1E N 0.3666 -0.2080 -0.0861 0.0843(12) Uani 0.56(2) 1 d P A 2 O1E O 0.3129 -0.2486 -0.0616 0.1300(16) Uani 0.56(2) 1 d P A 2 O2E O 0.5007 -0.2066 -0.1289 0.1129(11) Uani 0.56(2) 1 d P A 2 C1A C 0.2612 -0.1646 -0.0614 0.0711(5) Uani 1 1 d . A 2 C2A C 0.3155 -0.1196 -0.0896 0.0801(6) Uani 1 1 d . A 2 H2A H 0.4136 -0.1203 -0.1233 0.096 Uiso 1 1 calc R A 2 C3A C 0.2224 -0.0738 -0.0670 0.0759(5) Uani 1 1 d . A 2 H3A H 0.2563 -0.0433 -0.0860 0.091 Uiso 1 1 calc R A 2 C4A C 0.0784 -0.0717 -0.0165 0.0638(5) Uani 1 1 d . A 2 C5A C 0.0284 -0.1180 0.0104 0.0720(5) Uani 1 1 d . A 2 H5A H -0.0694 -0.1176 0.0442 0.086 Uiso 1 1 calc R A 2 C6A C 0.1195 -0.1646 -0.0114 0.0760(5) Uani 1 1 d . A 2 H6A H 0.0860 -0.1953 0.0072 0.091 Uiso 1 1 calc R A 2 C7A C -0.0238 -0.0232 0.0091 0.0726(5) Uani 1 1 d . A 2 H7A H -0.1337 -0.0261 0.0417 0.087 Uiso 1 1 calc R A 2 C11A C -0.2612 0.1646 0.0614 0.0711(5) Uani 1 1 d . A 2 C12A C -0.3155 0.1195 0.0896 0.0801(6) Uani 1 1 d . A 2 H12A H -0.4136 0.1203 0.1233 0.096 Uiso 1 1 calc R A 2 C13A C -0.2224 0.0738 0.0670 0.0759(5) Uani 1 1 d . A 2 H13A H -0.2563 0.0433 0.0859 0.091 Uiso 1 1 calc R A 2 C14A C -0.0784 0.0717 0.0164 0.0638(5) Uani 1 1 d . A 2 C15A C -0.0284 0.1180 -0.0105 0.0720(5) Uani 1 1 d . A 2 H15A H 0.0694 0.1176 -0.0442 0.086 Uiso 1 1 calc R A 2 C16A C -0.1195 0.1646 0.0114 0.0760(5) Uani 1 1 d . A 2 H16A H -0.0859 0.1953 -0.0072 0.091 Uiso 1 1 calc R A 2 C17A C 0.0237 0.0232 -0.0091 0.0726(5) Uani 1 1 d . A 2 H17A H 0.1337 0.0260 -0.0417 0.087 Uiso 1 1 calc R A 2 Cl1B Cl 0.3689 -0.2302 0.4123 0.1126(6) Uani 0.40(2) 1 d P B 3 N1B N -0.3666 0.2080 0.5861 0.0843(12) Uani 0.40(2) 1 d P B 3 O1B O -0.3129 0.2486 0.5616 0.1300(16) Uani 0.40(2) 1 d P B 3 O2B O -0.5007 0.2066 0.6289 0.1129(11) Uani 0.40(2) 1 d P B 3 Cl1F Cl -0.3689 0.2302 0.5877 0.1126(6) Uani 0.60(2) 1 d P B 4 N1F N 0.3666 -0.2080 0.4139 0.0843(12) Uani 0.60(2) 1 d P B 4 O1F O 0.3129 -0.2486 0.4384 0.1300(16) Uani 0.60(2) 1 d P B 4 O2F O 0.5007 -0.2066 0.3711 0.1129(11) Uani 0.60(2) 1 d P B 4 C1B C 0.2612 -0.1646 0.4386 0.0711(5) Uani 1 1 d . B 4 C2B C 0.3155 -0.1196 0.4104 0.0801(6) Uani 1 1 d . B 4 H2B H 0.4136 -0.1203 0.3767 0.096 Uiso 1 1 calc R B 4 C3B C 0.2224 -0.0738 0.4330 0.0759(5) Uani 1 1 d . B 4 H3B H 0.2563 -0.0433 0.4140 0.091 Uiso 1 1 calc R B 4 C4B C 0.0784 -0.0717 0.4835 0.0638(5) Uani 1 1 d . B 4 C5B C 0.0284 -0.1180 0.5104 0.0720(5) Uani 1 1 d . B 4 H5B H -0.0694 -0.1176 0.5442 0.086 Uiso 1 1 calc R B 4 C6B C 0.1195 -0.1646 0.4886 0.0760(5) Uani 1 1 d . B 4 H6B H 0.0860 -0.1953 0.5072 0.091 Uiso 1 1 calc R B 4 C7B C -0.0238 -0.0232 0.5091 0.0726(5) Uani 1 1 d . B 4 H7B H -0.1337 -0.0261 0.5417 0.087 Uiso 1 1 calc R B 4 C11B C -0.2612 0.1646 0.5614 0.0711(5) Uani 1 1 d . B 4 C12B C -0.3155 0.1195 0.5896 0.0801(6) Uani 1 1 d . B 4 H12B H -0.4136 0.1203 0.6233 0.096 Uiso 1 1 calc R B 4 C13B C -0.2224 0.0738 0.5670 0.0759(5) Uani 1 1 d . B 4 H13B H -0.2563 0.0433 0.5859 0.091 Uiso 1 1 calc R B 4 C14B C -0.0784 0.0717 0.5164 0.0638(5) Uani 1 1 d . B 4 C15B C -0.0284 0.1180 0.4895 0.0720(5) Uani 1 1 d . B 4 H15B H 0.0694 0.1176 0.4558 0.086 Uiso 1 1 calc R B 4 C16B C -0.1195 0.1646 0.5114 0.0760(5) Uani 1 1 d . B 4 H16B H -0.0859 0.1953 0.4928 0.091 Uiso 1 1 calc R B 4 C17B C 0.0237 0.0232 0.4909 0.0726(5) Uani 1 1 d . B 4 H17B H 0.1337 0.0260 0.4583 0.087 Uiso 1 1 calc R B 4 Cl1C Cl -0.3689 0.0198 0.3377 0.1126(6) Uani 0.513(6) 1 d P C 5 N1C N 0.3666 0.4580 0.1639 0.0843(12) Uani 0.513(6) 1 d P C 5 O1C O 0.3129 0.4986 0.1884 0.1300(16) Uani 0.513(6) 1 d P C 5 O2C O 0.5007 0.4566 0.1211 0.1129(11) Uani 0.513(6) 1 d P C 5 Cl1G Cl 0.3689 0.4802 0.1623 0.1126(6) Uani 0.487(6) 1 d P C 6 N1G N -0.3666 0.0420 0.3361 0.0843(12) Uani 0.487(6) 1 d P C 6 O1G O -0.3129 0.0014 0.3116 0.1300(16) Uani 0.487(6) 1 d P C 6 O2G O -0.5007 0.0434 0.3789 0.1129(11) Uani 0.487(6) 1 d P C 6 C1C C -0.2612 0.0854 0.3114 0.0711(5) Uani 1 1 d . C 6 C2C C -0.3155 0.1304 0.3396 0.0801(6) Uani 1 1 d . C 6 H2C H -0.4136 0.1297 0.3733 0.096 Uiso 1 1 calc R C 6 C3C C -0.2224 0.1762 0.3170 0.0759(5) Uani 1 1 d . C 6 H3C H -0.2563 0.2067 0.3360 0.091 Uiso 1 1 calc R C 6 C4C C -0.0784 0.1783 0.2664 0.0638(5) Uani 1 1 d . C 6 C5C C -0.0284 0.1320 0.2395 0.0720(5) Uani 1 1 d . C 6 H5C H 0.0694 0.1324 0.2058 0.086 Uiso 1 1 calc R C 6 C6C C -0.1195 0.0854 0.2614 0.0760(5) Uani 1 1 d . C 6 H6C H -0.0859 0.0547 0.2428 0.091 Uiso 1 1 calc R C 6 C7C C 0.0237 0.2268 0.2409 0.0726(5) Uani 1 1 d . C 6 H7C H 0.1337 0.2240 0.2083 0.087 Uiso 1 1 calc R C 6 C11C C 0.2612 0.4146 0.1886 0.0711(5) Uani 1 1 d . C 6 C12C C 0.3155 0.3695 0.1604 0.0801(6) Uani 1 1 d . C 6 H12C H 0.4136 0.3703 0.1267 0.096 Uiso 1 1 calc R C 6 C13C C 0.2224 0.3238 0.1830 0.0759(5) Uani 1 1 d . C 6 H13C H 0.2563 0.2933 0.1641 0.091 Uiso 1 1 calc R C 6 C14C C 0.0784 0.3217 0.2335 0.0638(5) Uani 1 1 d . C 6 C15C C 0.0284 0.3680 0.2604 0.0720(5) Uani 1 1 d . C 6 H15C H -0.0694 0.3676 0.2942 0.086 Uiso 1 1 calc R C 6 C16C C 0.1195 0.4146 0.2386 0.0760(5) Uani 1 1 d . C 6 H16C H 0.0860 0.4453 0.2572 0.091 Uiso 1 1 calc R C 6 C17C C -0.0238 0.2732 0.2591 0.0726(5) Uani 1 1 d . C 6 H17C H -0.1337 0.2760 0.2917 0.087 Uiso 1 1 calc R C 6 Cl1D Cl -0.3689 0.0198 -0.1623 0.1126(6) Uani 0.225(6) 1 d P D 7 N1D N 0.3666 0.4580 -0.3361 0.0843(12) Uani 0.225(6) 1 d P D 7 O1D O 0.3129 0.4986 -0.3116 0.1300(16) Uani 0.225(6) 1 d P D 7 O2D O 0.5007 0.4566 -0.3789 0.1129(11) Uani 0.225(6) 1 d P D 7 Cl1H Cl 0.3689 0.4802 -0.3377 0.1126(6) Uani 0.775(6) 1 d P D 8 N1H N -0.3666 0.0420 -0.1639 0.0843(12) Uani 0.775(6) 1 d P D 8 O1H O -0.3129 0.0014 -0.1884 0.1300(16) Uani 0.775(6) 1 d P D 8 O2H O -0.5007 0.0434 -0.1211 0.1129(11) Uani 0.775(6) 1 d P D 8 C1D C -0.2612 0.0854 -0.1886 0.0711(5) Uani 1 1 d . D 8 C2D C -0.3155 0.1304 -0.1604 0.0801(6) Uani 1 1 d . D 8 H2D H -0.4136 0.1297 -0.1267 0.096 Uiso 1 1 calc R D 8 C3D C -0.2224 0.1762 -0.1830 0.0759(5) Uani 1 1 d . D 8 H3D H -0.2563 0.2067 -0.1640 0.091 Uiso 1 1 calc R D 8 C4D C -0.0784 0.1783 -0.2336 0.0638(5) Uani 1 1 d . D 8 C5D C -0.0284 0.1320 -0.2605 0.0720(5) Uani 1 1 d . D 8 H5D H 0.0694 0.1324 -0.2942 0.086 Uiso 1 1 calc R D 8 C6D C -0.1195 0.0854 -0.2386 0.0760(5) Uani 1 1 d . D 8 H6D H -0.0859 0.0547 -0.2572 0.091 Uiso 1 1 calc R D 8 C7D C 0.0237 0.2268 -0.2591 0.0726(5) Uani 1 1 d . D 8 H7D H 0.1337 0.2240 -0.2917 0.087 Uiso 1 1 calc R D 8 C11D C 0.2612 0.4146 -0.3114 0.0711(5) Uani 1 1 d . D 8 C12D C 0.3155 0.3695 -0.3396 0.0801(6) Uani 1 1 d . D 8 H12D H 0.4136 0.3703 -0.3733 0.096 Uiso 1 1 calc R D 8 C13D C 0.2224 0.3238 -0.3170 0.0759(5) Uani 1 1 d . D 8 H13D H 0.2563 0.2933 -0.3359 0.091 Uiso 1 1 calc R D 8 C14D C 0.0784 0.3217 -0.2665 0.0638(5) Uani 1 1 d . D 8 C15D C 0.0284 0.3680 -0.2396 0.0720(5) Uani 1 1 d . D 8 H15D H -0.0694 0.3676 -0.2058 0.086 Uiso 1 1 calc R D 8 C16D C 0.1195 0.4146 -0.2614 0.0760(5) Uani 1 1 d . D 8 H16D H 0.0860 0.4453 -0.2428 0.091 Uiso 1 1 calc R D 8 C17D C -0.0238 0.2732 -0.2409 0.0726(5) Uani 1 1 d . D 8 H17D H -0.1337 0.2760 -0.2083 0.087 Uiso 1 1 calc R D 8 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1A 0.1123(12) 0.0908(10) 0.1348(15) -0.0477(10) 0.0072(10) 0.0207(8) N1A 0.082(3) 0.066(2) 0.103(3) -0.003(2) -0.007(2) 0.0002(18) O1A 0.170(4) 0.0702(19) 0.153(4) 0.008(2) 0.041(3) 0.014(2) O2A 0.153(3) 0.0897(19) 0.099(2) -0.0263(18) 0.036(2) 0.0179(19) Cl1E 0.1123(12) 0.0908(10) 0.1348(15) -0.0477(10) 0.0072(10) 0.0207(8) N1E 0.082(3) 0.066(2) 0.103(3) -0.003(2) -0.007(2) 0.0002(18) O1E 0.170(4) 0.0702(19) 0.153(4) 0.008(2) 0.041(3) 0.014(2) O2E 0.153(3) 0.0897(19) 0.099(2) -0.0263(18) 0.036(2) 0.0179(19) C1A 0.0573(11) 0.0816(12) 0.0737(13) -0.0182(10) -0.0034(9) 0.0046(10) C2A 0.0705(13) 0.1056(14) 0.0650(13) -0.0021(11) 0.0103(10) 0.0003(11) C3A 0.0691(13) 0.0823(12) 0.0765(14) 0.0087(10) 0.0071(10) -0.0035(10) C4A 0.0510(10) 0.0778(11) 0.0623(12) -0.0043(9) 0.0006(8) 0.0003(9) C5A 0.0695(12) 0.0839(12) 0.0630(12) 0.0020(10) 0.0079(9) -0.0013(10) C6A 0.0750(13) 0.0755(12) 0.0777(14) 0.0023(10) 0.0049(10) 0.0038(10) C7A 0.0612(11) 0.0837(12) 0.0730(13) 0.0045(10) 0.0052(9) -0.0034(10) C11A 0.0573(11) 0.0816(12) 0.0737(13) -0.0182(10) -0.0034(9) 0.0046(10) C12A 0.0705(13) 0.1056(14) 0.0650(13) -0.0021(11) 0.0103(10) 0.0003(11) C13A 0.0691(13) 0.0823(12) 0.0765(14) 0.0087(10) 0.0071(10) -0.0035(10) C14A 0.0510(10) 0.0778(11) 0.0623(12) -0.0043(9) 0.0006(8) 0.0003(9) C15A 0.0695(12) 0.0839(12) 0.0630(12) 0.0020(10) 0.0079(9) -0.0013(10) C16A 0.0750(13) 0.0755(12) 0.0777(14) 0.0023(10) 0.0049(10) 0.0038(10) C17A 0.0612(11) 0.0837(12) 0.0730(13) 0.0045(10) 0.0052(9) -0.0034(10) Cl1B 0.1123(12) 0.0908(10) 0.1348(15) -0.0477(10) 0.0072(10) 0.0207(8) N1B 0.082(3) 0.066(2) 0.103(3) -0.003(2) -0.007(2) 0.0002(18) O1B 0.170(4) 0.0702(19) 0.153(4) 0.008(2) 0.041(3) 0.014(2) O2B 0.153(3) 0.0897(19) 0.099(2) -0.0263(18) 0.036(2) 0.0179(19) Cl1F 0.1123(12) 0.0908(10) 0.1348(15) -0.0477(10) 0.0072(10) 0.0207(8) N1F 0.082(3) 0.066(2) 0.103(3) -0.003(2) -0.007(2) 0.0002(18) O1F 0.170(4) 0.0702(19) 0.153(4) 0.008(2) 0.041(3) 0.014(2) O2F 0.153(3) 0.0897(19) 0.099(2) -0.0263(18) 0.036(2) 0.0179(19) C1B 0.0573(11) 0.0816(12) 0.0737(13) -0.0182(10) -0.0034(9) 0.0046(10) C2B 0.0705(13) 0.1056(14) 0.0650(13) -0.0021(11) 0.0103(10) 0.0003(11) C3B 0.0691(13) 0.0823(12) 0.0765(14) 0.0087(10) 0.0071(10) -0.0035(10) C4B 0.0510(10) 0.0778(11) 0.0623(12) -0.0043(9) 0.0006(8) 0.0003(9) C5B 0.0695(12) 0.0839(12) 0.0630(12) 0.0020(10) 0.0079(9) -0.0013(10) C6B 0.0750(13) 0.0755(12) 0.0777(14) 0.0023(10) 0.0049(10) 0.0038(10) C7B 0.0612(11) 0.0837(12) 0.0730(13) 0.0045(10) 0.0052(9) -0.0034(10) C11B 0.0573(11) 0.0816(12) 0.0737(13) -0.0182(10) -0.0034(9) 0.0046(10) C12B 0.0705(13) 0.1056(14) 0.0650(13) -0.0021(11) 0.0103(10) 0.0003(11) C13B 0.0691(13) 0.0823(12) 0.0765(14) 0.0087(10) 0.0071(10) -0.0035(10) C14B 0.0510(10) 0.0778(11) 0.0623(12) -0.0043(9) 0.0006(8) 0.0003(9) C15B 0.0695(12) 0.0839(12) 0.0630(12) 0.0020(10) 0.0079(9) -0.0013(10) C16B 0.0750(13) 0.0755(12) 0.0777(14) 0.0023(10) 0.0049(10) 0.0038(10) C17B 0.0612(11) 0.0837(12) 0.0730(13) 0.0045(10) 0.0052(9) -0.0034(10) Cl1C 0.1123(12) 0.0908(10) 0.1348(15) 0.0477(10) 0.0072(10) -0.0207(8) N1C 0.082(3) 0.066(2) 0.103(3) 0.003(2) -0.007(2) -0.0002(18) O1C 0.170(4) 0.0702(19) 0.153(4) -0.008(2) 0.041(3) -0.014(2) O2C 0.153(3) 0.0897(19) 0.099(2) 0.0263(18) 0.036(2) -0.0179(19) Cl1G 0.1123(12) 0.0908(10) 0.1348(15) 0.0477(10) 0.0072(10) -0.0207(8) N1G 0.082(3) 0.066(2) 0.103(3) 0.003(2) -0.007(2) -0.0002(18) O1G 0.170(4) 0.0702(19) 0.153(4) -0.008(2) 0.041(3) -0.014(2) O2G 0.153(3) 0.0897(19) 0.099(2) 0.0263(18) 0.036(2) -0.0179(19) C1C 0.0573(11) 0.0816(12) 0.0737(13) 0.0182(10) -0.0034(9) -0.0046(10) C2C 0.0705(13) 0.1056(14) 0.0650(13) 0.0021(11) 0.0103(10) -0.0003(11) C3C 0.0691(13) 0.0823(12) 0.0765(14) -0.0087(10) 0.0071(10) 0.0035(10) C4C 0.0510(10) 0.0778(11) 0.0623(12) 0.0043(9) 0.0006(8) -0.0003(9) C5C 0.0695(12) 0.0839(12) 0.0630(12) -0.0020(10) 0.0079(9) 0.0013(10) C6C 0.0750(13) 0.0755(12) 0.0777(14) -0.0023(10) 0.0049(10) -0.0038(10) C7C 0.0612(11) 0.0837(12) 0.0730(13) -0.0045(10) 0.0052(9) 0.0034(10) C11C 0.0573(11) 0.0816(12) 0.0737(13) 0.0182(10) -0.0034(9) -0.0046(10) C12C 0.0705(13) 0.1056(14) 0.0650(13) 0.0021(11) 0.0103(10) -0.0003(11) C13C 0.0691(13) 0.0823(12) 0.0765(14) -0.0087(10) 0.0071(10) 0.0035(10) C14C 0.0510(10) 0.0778(11) 0.0623(12) 0.0043(9) 0.0006(8) -0.0003(9) C15C 0.0695(12) 0.0839(12) 0.0630(12) -0.0020(10) 0.0079(9) 0.0013(10) C16C 0.0750(13) 0.0755(12) 0.0777(14) -0.0023(10) 0.0049(10) -0.0038(10) C17C 0.0612(11) 0.0837(12) 0.0730(13) -0.0045(10) 0.0052(9) 0.0034(10) Cl1D 0.1123(12) 0.0908(10) 0.1348(15) 0.0477(10) 0.0072(10) -0.0207(8) N1D 0.082(3) 0.066(2) 0.103(3) 0.003(2) -0.007(2) -0.0002(18) O1D 0.170(4) 0.0702(19) 0.153(4) -0.008(2) 0.041(3) -0.014(2) O2D 0.153(3) 0.0897(19) 0.099(2) 0.0263(18) 0.036(2) -0.0179(19) Cl1H 0.1123(12) 0.0908(10) 0.1348(15) 0.0477(10) 0.0072(10) -0.0207(8) N1H 0.082(3) 0.066(2) 0.103(3) 0.003(2) -0.007(2) -0.0002(18) O1H 0.170(4) 0.0702(19) 0.153(4) -0.008(2) 0.041(3) -0.014(2) O2H 0.153(3) 0.0897(19) 0.099(2) 0.0263(18) 0.036(2) -0.0179(19) C1D 0.0573(11) 0.0816(12) 0.0737(13) 0.0182(10) -0.0034(9) -0.0046(10) C2D 0.0705(13) 0.1056(14) 0.0650(13) 0.0021(11) 0.0103(10) -0.0003(11) C3D 0.0691(13) 0.0823(12) 0.0765(14) -0.0087(10) 0.0071(10) 0.0035(10) C4D 0.0510(10) 0.0778(11) 0.0623(12) 0.0043(9) 0.0006(8) -0.0003(9) C5D 0.0695(12) 0.0839(12) 0.0630(12) -0.0020(10) 0.0079(9) 0.0013(10) C6D 0.0750(13) 0.0755(12) 0.0777(14) -0.0023(10) 0.0049(10) -0.0038(10) C7D 0.0612(11) 0.0837(12) 0.0730(13) -0.0045(10) 0.0052(9) 0.0034(10) C11D 0.0573(11) 0.0816(12) 0.0737(13) 0.0182(10) -0.0034(9) -0.0046(10) C12D 0.0705(13) 0.1056(14) 0.0650(13) 0.0021(11) 0.0103(10) -0.0003(11) C13D 0.0691(13) 0.0823(12) 0.0765(14) -0.0087(10) 0.0071(10) 0.0035(10) C14D 0.0510(10) 0.0778(11) 0.0623(12) 0.0043(9) 0.0006(8) -0.0003(9) C15D 0.0695(12) 0.0839(12) 0.0630(12) -0.0020(10) 0.0079(9) 0.0013(10) C16D 0.0750(13) 0.0755(12) 0.0777(14) -0.0023(10) 0.0049(10) -0.0038(10) C17D 0.0612(11) 0.0837(12) 0.0730(13) -0.0045(10) 0.0052(9) 0.0034(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1A O2A 1.1984 . ? N1A O1A 1.2361 . ? Cl1E C11A 1.8774 . ? N1E O2E 1.1981 . ? N1E O1E 1.2359 . ? N1E C1A 1.3539 . ? C1A C6A 1.3733 . ? C1A C2A 1.3787 . ? C2A C3A 1.3688 . ? C2A H2A 0.9300 . ? C3A C4A 1.3895 . ? C3A H3A 0.9300 . ? C4A C5A 1.3910 . ? C4A C7A 1.4690 . ? C5A C6A 1.3777 . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? C7A C17A 1.3027 . ? C7A H7A 0.9300 . ? C11A C16A 1.3730 . ? C11A C12A 1.3786 . ? C12A C13A 1.3685 . ? C12A H12A 0.9300 . ? C13A C14A 1.3896 . ? C13A H13A 0.9300 . ? C14A C15A 1.3909 . ? C14A C17A 1.4693 . ? C15A C16A 1.3779 . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? C17A H17A 0.9300 . ? N1B O2B 1.1984 . ? N1B O1B 1.2361 . ? Cl1F C11B 1.8774 . ? N1F O2F 1.1981 . ? N1F O1F 1.2359 . ? N1F C1B 1.3539 . ? C1B C6B 1.3733 . ? C1B C2B 1.3787 . ? C2B C3B 1.3688 . ? C2B H2B 0.9300 . ? C3B C4B 1.3895 . ? C3B H3B 0.9300 . ? C4B C5B 1.3910 . ? C4B C7B 1.4690 . ? C5B C6B 1.3777 . ? C5B H5B 0.9300 . ? C6B H6B 0.9300 . ? C7B C17B 1.3027 . ? C7B H7B 0.9300 . ? C11B C16B 1.3730 . ? C11B C12B 1.3786 . ? C12B C13B 1.3685 . ? C12B H12B 0.9300 . ? C13B C14B 1.3896 . ? C13B H13B 0.9300 . ? C14B C15B 1.3909 . ? C14B C17B 1.4693 . ? C15B C16B 1.3779 . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? C17B H17B 0.9300 . ? N1C O2C 1.1981 . ? N1C O1C 1.2360 . ? Cl1G C11C 1.8776 . ? N1G O2G 1.1981 . ? N1G O1G 1.2360 . ? N1G C1C 1.3540 . ? C1C C6C 1.3730 . ? C1C C2C 1.3786 . ? C2C C3C 1.3686 . ? C2C H2C 0.9300 . ? C3C C4C 1.3896 . ? C3C H3C 0.9300 . ? C4C C5C 1.3911 . ? C4C C7C 1.4691 . ? C5C C6C 1.3780 . ? C5C H5C 0.9300 . ? C6C H6C 0.9300 . ? C7C C17C 1.3024 . ? C7C H7C 0.9300 . ? C11C C16C 1.3730 . ? C11C C12C 1.3785 . ? C12C C13C 1.3684 . ? C12C H12C 0.9300 . ? C13C C14C 1.3893 . ? C13C H13C 0.9300 . ? C14C C15C 1.3906 . ? C14C C17C 1.4697 . ? C15C C16C 1.3774 . ? C15C H15C 0.9300 . ? C16C H16C 0.9300 . ? C17C H17C 0.9300 . ? N1D O2D 1.1981 . ? N1D O1D 1.2360 . ? Cl1H C11D 1.8776 . ? N1H O2H 1.1981 . ? N1H O1H 1.2360 . ? N1H C1D 1.3540 . ? C1D C6D 1.3730 . ? C1D C2D 1.3786 . ? C2D C3D 1.3686 . ? C2D H2D 0.9300 . ? C3D C4D 1.3896 . ? C3D H3D 0.9300 . ? C4D C5D 1.3911 . ? C4D C7D 1.4691 . ? C5D C6D 1.3780 . ? C5D H5D 0.9300 . ? C6D H6D 0.9300 . ? C7D C17D 1.3024 . ? C7D H7D 0.9300 . ? C11D C16D 1.3730 . ? C11D C12D 1.3785 . ? C12D C13D 1.3684 . ? C12D H12D 0.9300 . ? C13D C14D 1.3893 . ? C13D H13D 0.9300 . ? C14D C15D 1.3906 . ? C14D C17D 1.4697 . ? C15D C16D 1.3774 . ? C15D H15D 0.9300 . ? C16D H16D 0.9300 . ? C17D H17D 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2A N1A O1A 123.117(1) . . ? O2E N1E O1E 123.102(1) . . ? O2E N1E C1A 121.6 . . ? O1E N1E C1A 115.279(2) . . ? N1E C1A C6A 123.087(1) . . ? N1E C1A C2A 114.990(2) . . ? C6A C1A C2A 121.898(1) . . ? C3A C2A C1A 118.788(1) . . ? C3A C2A H2A 120.6 . . ? C1A C2A H2A 120.6 . . ? C2A C3A C4A 121.651(2) . . ? C2A C3A H3A 119.2 . . ? C4A C3A H3A 119.2 . . ? C3A C4A C5A 117.554(1) . . ? C3A C4A C7A 123.173(1) . . ? C5A C4A C7A 119.272(2) . . ? C6A C5A C4A 121.961(1) . . ? C6A C5A H5A 119.0 . . ? C4A C5A H5A 119.0 . . ? C1A C6A C5A 118.144(2) . . ? C1A C6A H6A 120.9 . . ? C5A C6A H6A 120.9 . . ? C17A C7A C4A 126.721(2) . . ? C17A C7A H7A 116.6 . . ? C4A C7A H7A 116.6 . . ? C16A C11A C12A 121.899(2) . . ? C16A C11A Cl1E 114.473(2) . . ? C12A C11A Cl1E 123.626(2) . . ? C13A C12A C11A 118.801(2) . . ? C13A C12A H12A 120.6 . . ? C11A C12A H12A 120.6 . . ? C12A C13A C14A 121.633(1) . . ? C12A C13A H13A 119.2 . . ? C14A C13A H13A 119.2 . . ? C13A C14A C15A 117.575(1) . . ? C13A C14A C17A 123.148(1) . . ? C15A C14A C17A 119.275(1) . . ? C16A C15A C14A 121.929(1) . . ? C16A C15A H15A 119.0 . . ? C14A C15A H15A 119.0 . . ? C11A C16A C15A 118.2 . . ? C11A C16A H16A 120.9 . . ? C15A C16A H16A 120.9 . . ? C7A C17A C14A 126.736(2) . . ? C7A C17A H17A 116.6 . . ? C14A C17A H17A 116.6 . . ? O2B N1B O1B 123.117(1) . . ? O2F N1F O1F 123.102(2) . . ? O2F N1F C1B 121.618(1) . . ? O1F N1F C1B 115.279(2) . . ? N1F C1B C6B 123.087(1) . . ? N1F C1B C2B 114.990(2) . . ? C6B C1B C2B 121.898(1) . . ? C3B C2B C1B 118.788(1) . . ? C3B C2B H2B 120.6 . . ? C1B C2B H2B 120.6 . . ? C2B C3B C4B 121.7 . . ? C2B C3B H3B 119.2 . . ? C4B C3B H3B 119.2 . . ? C3B C4B C5B 117.554(1) . . ? C3B C4B C7B 123.173(2) . . ? C5B C4B C7B 119.272(2) . . ? C6B C5B C4B 121.961(2) . . ? C6B C5B H5B 119.0 . . ? C4B C5B H5B 119.0 . . ? C1B C6B C5B 118.144(1) . . ? C1B C6B H6B 120.9 . . ? C5B C6B H6B 120.9 . . ? C17B C7B C4B 126.721(1) . . ? C17B C7B H7B 116.6 . . ? C4B C7B H7B 116.6 . . ? C16B C11B C12B 121.899(1) . . ? C16B C11B Cl1F 114.473(1) . . ? C12B C11B Cl1F 123.626(2) . . ? C13B C12B C11B 118.801(2) . . ? C13B C12B H12B 120.6 . . ? C11B C12B H12B 120.6 . . ? C12B C13B C14B 121.633(1) . . ? C12B C13B H13B 119.2 . . ? C14B C13B H13B 119.2 . . ? C13B C14B C15B 117.575(1) . . ? C13B C14B C17B 123.148(1) . . ? C15B C14B C17B 119.275(2) . . ? C16B C15B C14B 121.929(2) . . ? C16B C15B H15B 119.0 . . ? C14B C15B H15B 119.0 . . ? C11B C16B C15B 118.157(2) . . ? C11B C16B H16B 120.9 . . ? C15B C16B H16B 120.9 . . ? C7B C17B C14B 126.736(2) . . ? C7B C17B H17B 116.6 . . ? C14B C17B H17B 116.6 . . ? O2C N1C O1C 123.113(1) . . ? O2G N1G O1G 123.109(1) . . ? O2G N1G C1C 121.626(2) . . ? O1G N1G C1C 115.264(2) . . ? N1G C1C C6C 123.095(1) . . ? N1G C1C C2C 114.989(2) . . ? C6C C1C C2C 121.890(1) . . ? C3C C2C C1C 118.806(2) . . ? C3C C2C H2C 120.6 . . ? C1C C2C H2C 120.6 . . ? C2C C3C C4C 121.640(1) . . ? C2C C3C H3C 119.2 . . ? C4C C3C H3C 119.2 . . ? C3C C4C C5C 117.562(1) . . ? C3C C4C C7C 123.163(1) . . ? C5C C4C C7C 119.274(1) . . ? C6C C5C C4C 121.934(2) . . ? C6C C5C H5C 119.0 . . ? C4C C5C H5C 119.0 . . ? C1C C6C C5C 118.164(1) . . ? C1C C6C H6C 120.9 . . ? C5C C6C H6C 120.9 . . ? C17C C7C C4C 126.725(1) . . ? C17C C7C H7C 116.6 . . ? C4C C7C H7C 116.6 . . ? C16C C11C C12C 121.913(2) . . ? C16C C11C Cl1G 114.463(2) . . ? C12C C11C Cl1G 123.622(2) . . ? C13C C12C C11C 118.774(2) . . ? C13C C12C H12C 120.6 . . ? C11C C12C H12C 120.6 . . ? C12C C13C C14C 121.648(2) . . ? C12C C13C H13C 119.2 . . ? C14C C13C H13C 119.2 . . ? C13C C14C C15C 117.572(2) . . ? C13C C14C C17C 123.146(1) . . ? C15C C14C C17C 119.281(2) . . ? C16C C15C C14C 121.946(2) . . ? C16C C15C H15C 119.0 . . ? C14C C15C H15C 119.0 . . ? C11C C16C C15C 118.143(1) . . ? C11C C16C H16C 120.9 . . ? C15C C16C H16C 120.9 . . ? C7C C17C C14C 126.733(2) . . ? C7C C17C H17C 116.6 . . ? C14C C17C H17C 116.6 . . ? O2D N1D O1D 123.113(1) . . ? O2H N1H O1H 123.109(1) . . ? O2H N1H C1D 121.626(1) . . ? O1H N1H C1D 115.264(2) . . ? N1H C1D C6D 123.095(1) . . ? N1H C1D C2D 114.989(2) . . ? C6D C1D C2D 121.890(1) . . ? C3D C2D C1D 118.806(2) . . ? C3D C2D H2D 120.6 . . ? C1D C2D H2D 120.6 . . ? C2D C3D C4D 121.640(1) . . ? C2D C3D H3D 119.2 . . ? C4D C3D H3D 119.2 . . ? C3D C4D C5D 117.562(2) . . ? C3D C4D C7D 123.2 . . ? C5D C4D C7D 119.274(2) . . ? C6D C5D C4D 121.934(2) . . ? C6D C5D H5D 119.0 . . ? C4D C5D H5D 119.0 . . ? C1D C6D C5D 118.164(1) . . ? C1D C6D H6D 120.9 . . ? C5D C6D H6D 120.9 . . ? C17D C7D C4D 126.725(1) . . ? C17D C7D H7D 116.6 . . ? C4D C7D H7D 116.6 . . ? C16D C11D C12D 121.913(1) . . ? C16D C11D Cl1H 114.463(2) . . ? C12D C11D Cl1H 123.622(3) . . ? C13D C12D C11D 118.774(3) . . ? C13D C12D H12D 120.6 . . ? C11D C12D H12D 120.6 . . ? C12D C13D C14D 121.6 . . ? C12D C13D H13D 119.2 . . ? C14D C13D H13D 119.2 . . ? C13D C14D C15D 117.572(2) . . ? C13D C14D C17D 123.1 . . ? C15D C14D C17D 119.281(2) . . ? C16D C15D C14D 121.946(2) . . ? C16D C15D H15D 119.0 . . ? C14D C15D H15D 119.0 . . ? C11D C16D C15D 118.143(1) . . ? C11D C16D H16D 120.9 . . ? C15D C16D H16D 120.9 . . ? C7D C17D C14D 126.733(2) . . ? C7D C17D H17D 116.6 . . ? C14D C17D H17D 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2E N1E C1A C6A -177.3 . . . . ? O1E N1E C1A C6A 3.1 . . . . ? O2E N1E C1A C2A 0.9 . . . . ? O1E N1E C1A C2A -178.7 . . . . ? N1E C1A C2A C3A -178.8 . . . . ? C6A C1A C2A C3A -0.6 . . . . ? C1A C2A C3A C4A 0.6 . . . . ? C2A C3A C4A C5A -0.6 . . . . ? C2A C3A C4A C7A 179.8 . . . . ? C3A C4A C5A C6A 0.5 . . . . ? C7A C4A C5A C6A -179.9 . . . . ? N1E C1A C6A C5A 178.5 . . . . ? C2A C1A C6A C5A 0.5 . . . . ? C4A C5A C6A C1A -0.5 . . . . ? C3A C4A C7A C17A -4.7 . . . . ? C5A C4A C7A C17A 175.7 . . . . ? C16A C11A C12A C13A 0.6 . . . . ? Cl1E C11A C12A C13A -179.0 . . . . ? C11A C12A C13A C14A -0.6 . . . . ? C12A C13A C14A C15A 0.6 . . . . ? C12A C13A C14A C17A -179.8 . . . . ? C13A C14A C15A C16A -0.5 . . . . ? C17A C14A C15A C16A 179.9 . . . . ? C12A C11A C16A C15A -0.472(1) . . . . ? Cl1E C11A C16A C15A 179.1 . . . . ? C14A C15A C16A C11A 0.5 . . . . ? C4A C7A C17A C14A 180.0 . . . . ? C13A C14A C17A C7A 4.7 . . . . ? C15A C14A C17A C7A -175.7 . . . . ? O2F N1F C1B C6B -177.3 . . . . ? O1F N1F C1B C6B 3.1 . . . . ? O2F N1F C1B C2B 0.9 . . . . ? O1F N1F C1B C2B -178.7 . . . . ? N1F C1B C2B C3B -178.8 . . . . ? C6B C1B C2B C3B -0.6 . . . . ? C1B C2B C3B C4B 0.6 . . . . ? C2B C3B C4B C5B -0.6 . . . . ? C2B C3B C4B C7B 179.8 . . . . ? C3B C4B C5B C6B 0.5 . . . . ? C7B C4B C5B C6B -179.9 . . . . ? N1F C1B C6B C5B 178.5 . . . . ? C2B C1B C6B C5B 0.5 . . . . ? C4B C5B C6B C1B -0.5 . . . . ? C3B C4B C7B C17B -4.7 . . . . ? C5B C4B C7B C17B 175.7 . . . . ? C16B C11B C12B C13B 0.6 . . . . ? Cl1F C11B C12B C13B -179.0 . . . . ? C11B C12B C13B C14B -0.6 . . . . ? C12B C13B C14B C15B 0.6 . . . . ? C12B C13B C14B C17B -179.8 . . . . ? C13B C14B C15B C16B -0.5 . . . . ? C17B C14B C15B C16B 179.9 . . . . ? C12B C11B C16B C15B -0.5 . . . . ? Cl1F C11B C16B C15B 179.1 . . . . ? C14B C15B C16B C11B 0.5 . . . . ? C4B C7B C17B C14B 180.0 . . . . ? C13B C14B C17B C7B 4.7 . . . . ? C15B C14B C17B C7B -175.7 . . . . ? O2G N1G C1C C6C -177.3 . . . . ? O1G N1G C1C C6C 3.1 . . . . ? O2G N1G C1C C2C 0.9 . . . . ? O1G N1G C1C C2C -178.7 . . . . ? N1G C1C C2C C3C -178.8 . . . . ? C6C C1C C2C C3C -0.6 . . . . ? C1C C2C C3C C4C 0.6 . . . . ? C2C C3C C4C C5C -0.6 . . . . ? C2C C3C C4C C7C 179.8 . . . . ? C3C C4C C5C C6C 0.5 . . . . ? C7C C4C C5C C6C -179.9 . . . . ? N1G C1C C6C C5C 178.531(2) . . . . ? C2C C1C C6C C5C 0.5 . . . . ? C4C C5C C6C C1C -0.5 . . . . ? C3C C4C C7C C17C -4.7 . . . . ? C5C C4C C7C C17C 175.7 . . . . ? C16C C11C C12C C13C 0.6 . . . . ? Cl1G C11C C12C C13C -179.0 . . . . ? C11C C12C C13C C14C -0.6 . . . . ? C12C C13C C14C C15C 0.607(2) . . . . ? C12C C13C C14C C17C -179.8 . . . . ? C13C C14C C15C C16C -0.5 . . . . ? C17C C14C C15C C16C 179.9 . . . . ? C12C C11C C16C C15C -0.5 . . . . ? Cl1G C11C C16C C15C 179.1 . . . . ? C14C C15C C16C C11C 0.5 . . . . ? C4C C7C C17C C14C 180.0 . . . . ? C13C C14C C17C C7C 4.732(1) . . . . ? C15C C14C C17C C7C -175.7 . . . . ? O2H N1H C1D C6D -177.3 . . . . ? O1H N1H C1D C6D 3.1 . . . . ? O2H N1H C1D C2D 0.9 . . . . ? O1H N1H C1D C2D -178.7 . . . . ? N1H C1D C2D C3D -178.8 . . . . ? C6D C1D C2D C3D -0.6 . . . . ? C1D C2D C3D C4D 0.630(1) . . . . ? C2D C3D C4D C5D -0.6 . . . . ? C2D C3D C4D C7D 179.8 . . . . ? C3D C4D C5D C6D 0.5 . . . . ? C7D C4D C5D C6D -179.9 . . . . ? N1H C1D C6D C5D 178.5 . . . . ? C2D C1D C6D C5D 0.5 . . . . ? C4D C5D C6D C1D -0.5 . . . . ? C3D C4D C7D C17D -4.7 . . . . ? C5D C4D C7D C17D 175.7 . . . . ? C16D C11D C12D C13D 0.6 . . . . ? Cl1H C11D C12D C13D -179.0 . . . . ? C11D C12D C13D C14D -0.6 . . . . ? C12D C13D C14D C15D 0.6 . . . . ? C12D C13D C14D C17D -179.8 . . . . ? C13D C14D C15D C16D -0.5 . . . . ? C17D C14D C15D C16D 179.9 . . . . ? C12D C11D C16D C15D -0.5 . . . . ? Cl1H C11D C16D C15D 179.1 . . . . ? C14D C15D C16D C11D 0.5 . . . . ? C4D C7D C17D C14D 180.0 . . . . ? C13D C14D C17D C7D 4.732(1) . . . . ? C15D C14D C17D C7D -175.7 . . . . ? _diffrn_measured_fraction_theta_max 0.498 _diffrn_reflns_theta_full 27.78 _diffrn_measured_fraction_theta_full 0.498 _refine_diff_density_max 0.139 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.034 # start Validation Reply Form _vrf_REFLT03_CNS-TolII-big-A1 ; PROBLEM: Reflection count < 85% complete (theta max?) RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. The measurement was performed in a hemisphere strategy. ; _vrf_SYMMG01_CNS-TolII-big-A1 ; PROBLEM: Unrecognised _symmetry_space_group_name_H-M RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. ; _vrf_SYMMG02_CNS-TolII-big-A1 ; PROBLEM: Supplied _symmetry_space_group_name_H-M not recognised RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. ; _vrf_PLAT029_CNS-TolII-big-A1 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.50 RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. The measurement was performed in a hemisphere strategy. ; # end Validation Reply Form #===END data_CNS-NO2BzI-small-P21_c _database_code_depnum_ccdc_archive 'CCDC 761216' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9220(2) _cell_length_b 12.9245(7) _cell_length_c 12.3038(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.957(2) _cell_angle_gamma 90.00 _cell_volume 622.85(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3497 _cell_measurement_theta_min 2.287 _cell_measurement_theta_max 23.0145 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.605731 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3484 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.83 _reflns_number_total 2158 _reflns_number_gt 1124 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0824P)^2^+0.0374P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 2158 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1858 _refine_ls_wR_factor_gt 0.1541 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3740(12) -0.46135(16) -0.1771(4) 0.1402(18) Uani 0.50 1 d P . . N11 N 0.365(2) -0.4138(5) -0.1721(6) 0.0879(15) Uani 0.50 1 d P . . O11 O 0.320(2) -0.4987(7) -0.1291(5) 0.152(3) Uani 0.50 1 d P . . O12 O 0.5052(9) -0.4076(3) -0.2625(3) 0.1239(12) Uani 0.50 1 d P . . C1 C 0.2614(4) -0.32881(16) -0.12380(16) 0.0815(6) Uani 1 1 d . . . C2 C 0.3130(4) -0.2377(2) -0.17815(14) 0.0919(6) Uani 1 1 d . . . H2A H 0.4115 -0.2382 -0.2453 0.110 Uiso 1 1 calc R . . C3 C 0.2200(5) -0.14761(17) -0.13341(16) 0.0908(6) Uani 1 1 d . . . H3A H 0.2523 -0.0862 -0.1709 0.109 Uiso 1 1 calc R . . C4 C 0.0771(4) -0.14431(14) -0.03284(15) 0.0775(5) Uani 1 1 d . . . C5 C 0.0272(4) -0.23764(16) 0.02102(14) 0.0835(6) Uani 1 1 d . . . H5A H -0.0706 -0.2371 0.0883 0.100 Uiso 1 1 calc R . . C6 C 0.1204(5) -0.33073(14) -0.02363(16) 0.0856(6) Uani 1 1 d . . . H6A H 0.0889 -0.3928 0.0128 0.103 Uiso 1 1 calc R . . C7 C -0.0236(5) -0.04756(15) 0.01830(16) 0.0921(6) Uani 1 1 d . . . H7A H -0.1324 -0.0534 0.0834 0.111 Uiso 1 1 calc R . . Cl11 Cl -0.3740(12) 0.46135(16) 0.1771(4) 0.1402(18) Uani 0.50 1 d P . . N1 N -0.365(2) 0.4138(5) 0.1721(6) 0.0879(15) Uani 0.50 1 d P . . O1 O -0.320(2) 0.4987(7) 0.1291(5) 0.152(3) Uani 0.50 1 d P . . O2 O -0.5052(9) 0.4076(3) 0.2625(3) 0.1239(12) Uani 0.50 1 d P . . C11 C -0.2614(4) 0.32881(16) 0.12380(16) 0.0815(6) Uani 1 1 d . . . C12 C -0.3130(4) 0.2377(2) 0.17815(14) 0.0919(6) Uani 1 1 d . . . H12A H -0.4115 0.2382 0.2453 0.110 Uiso 1 1 calc R . . C13 C -0.2200(5) 0.14761(17) 0.13341(16) 0.0908(6) Uani 1 1 d . . . H13A H -0.2523 0.0862 0.1709 0.109 Uiso 1 1 calc R . . C14 C -0.0771(4) 0.14431(14) 0.03284(15) 0.0775(5) Uani 1 1 d . . . C15 C -0.0272(4) 0.23764(16) -0.02102(14) 0.0835(6) Uani 1 1 d . . . H15A H 0.0706 0.2371 -0.0883 0.100 Uiso 1 1 calc R . . C16 C -0.1204(5) 0.33073(14) 0.02363(16) 0.0856(6) Uani 1 1 d . . . H16A H -0.0889 0.3928 -0.0128 0.103 Uiso 1 1 calc R . . C17 C 0.0236(5) 0.04756(15) -0.01830(16) 0.0921(6) Uani 1 1 d . . . H17A H 0.1324 0.0534 -0.0834 0.111 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1234(15) 0.127(4) 0.170(3) -0.070(3) 0.0007(16) 0.029(2) N11 0.081(3) 0.088(5) 0.095(4) -0.016(4) 0.004(2) 0.010(4) O11 0.174(4) 0.096(3) 0.190(6) 0.006(3) 0.046(3) 0.014(3) O12 0.150(3) 0.127(3) 0.098(2) -0.0250(19) 0.0392(19) 0.023(2) C1 0.0610(10) 0.0988(15) 0.0844(13) -0.0122(11) -0.0003(8) 0.0042(10) C2 0.0745(12) 0.1226(18) 0.0795(13) 0.0019(12) 0.0110(9) -0.0024(12) C3 0.0788(12) 0.1011(15) 0.0929(14) 0.0135(11) 0.0091(10) -0.0038(11) C4 0.0605(9) 0.0846(13) 0.0870(13) -0.0073(10) 0.0011(8) -0.0001(9) C5 0.0727(11) 0.1031(15) 0.0755(11) -0.0027(11) 0.0107(8) 0.0005(10) C6 0.0780(11) 0.0915(14) 0.0876(13) 0.0054(10) 0.0061(9) 0.0005(10) C7 0.0740(11) 0.1103(16) 0.0926(13) 0.0102(11) 0.0102(9) -0.0070(12) Cl11 0.1234(15) 0.127(4) 0.170(3) -0.070(3) 0.0007(16) 0.029(2) N1 0.081(3) 0.088(5) 0.095(4) -0.016(4) 0.004(2) 0.010(4) O1 0.174(4) 0.096(3) 0.190(6) 0.006(3) 0.046(3) 0.014(3) O2 0.150(3) 0.127(3) 0.098(2) -0.0250(19) 0.0392(19) 0.023(2) C11 0.0610(10) 0.0988(15) 0.0844(13) -0.0122(11) -0.0003(8) 0.0042(10) C12 0.0745(12) 0.1226(18) 0.0795(13) 0.0019(12) 0.0110(9) -0.0024(12) C13 0.0788(12) 0.1011(15) 0.0929(14) 0.0135(11) 0.0091(10) -0.0038(11) C14 0.0605(9) 0.0846(13) 0.0870(13) -0.0073(10) 0.0011(8) -0.0001(9) C15 0.0727(11) 0.1031(15) 0.0755(11) -0.0027(11) 0.0107(8) 0.0005(10) C16 0.0780(11) 0.0915(14) 0.0876(13) 0.0054(10) 0.0061(9) 0.0005(10) C17 0.0740(11) 0.1103(16) 0.0926(13) 0.0102(11) 0.0102(9) -0.0070(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.619(6) . ? Cl1 O11 0.799(6) . ? Cl1 O12 1.381(5) . ? Cl1 C1 1.894(3) . ? N11 O11 1.234(14) . ? N11 O12 1.269(9) . ? N11 C1 1.322(5) . ? C1 C2 1.375(3) . ? C1 C6 1.377(3) . ? C2 C3 1.346(3) . ? C2 H2A 0.9300 . ? C3 C4 1.385(3) . ? C3 H3A 0.9300 . ? C4 C5 1.395(3) . ? C4 C7 1.463(3) . ? C5 C6 1.380(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.326(3) . ? C7 H7A 0.9300 . ? Cl11 N1 0.619(6) . ? Cl11 O1 0.799(6) . ? Cl11 O2 1.381(5) . ? Cl11 C11 1.894(3) . ? N1 O1 1.234(14) . ? N1 O2 1.269(9) . ? N1 C11 1.322(5) . ? C11 C12 1.375(3) . ? C11 C16 1.377(3) . ? C12 C13 1.346(3) . ? C12 H12A 0.9300 . ? C13 C14 1.385(3) . ? C13 H13A 0.9300 . ? C14 C15 1.395(3) . ? C14 C17 1.463(3) . ? C15 C16 1.380(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 120.5(19) . . ? N11 Cl1 O12 66.6(12) . . ? O11 Cl1 O12 171.4(9) . . ? N11 Cl1 C1 18.5(11) . . ? O11 Cl1 C1 102.4(9) . . ? O12 Cl1 C1 84.9(2) . . ? Cl1 N11 O11 33.9(12) . . ? Cl1 N11 O12 86.9(11) . . ? O11 N11 O12 120.6(6) . . ? Cl1 N11 C1 152.9(16) . . ? O11 N11 C1 119.5(6) . . ? O12 N11 C1 119.9(7) . . ? Cl1 O11 N11 25.6(6) . . ? N11 O12 Cl1 26.6(3) . . ? N11 C1 C2 115.9(4) . . ? N11 C1 C6 122.3(4) . . ? C2 C1 C6 121.80(19) . . ? N11 C1 Cl1 8.6(5) . . ? C2 C1 Cl1 124.3(2) . . ? C6 C1 Cl1 113.9(2) . . ? C3 C2 C1 119.48(19) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 121.5(2) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 118.09(18) . . ? C3 C4 C7 122.8(2) . . ? C5 C4 C7 119.15(18) . . ? C6 C5 C4 121.23(17) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C1 C6 C5 117.87(18) . . ? C1 C6 H6A 121.1 . . ? C5 C6 H6A 121.1 . . ? C17 C7 C4 126.9(3) . . ? C17 C7 H7A 116.5 . . ? C4 C7 H7A 116.5 . . ? N1 Cl11 O1 120.5(19) . . ? N1 Cl11 O2 66.6(12) . . ? O1 Cl11 O2 171.4(9) . . ? N1 Cl11 C11 18.5(11) . . ? O1 Cl11 C11 102.4(9) . . ? O2 Cl11 C11 84.9(2) . . ? Cl11 N1 O1 33.9(12) . . ? Cl11 N1 O2 86.9(11) . . ? O1 N1 O2 120.6(6) . . ? Cl11 N1 C11 152.9(16) . . ? O1 N1 C11 119.5(6) . . ? O2 N1 C11 119.9(7) . . ? Cl11 O1 N1 25.6(6) . . ? N1 O2 Cl11 26.6(3) . . ? N1 C11 C12 115.9(4) . . ? N1 C11 C16 122.3(4) . . ? C12 C11 C16 121.80(19) . . ? N1 C11 Cl11 8.6(5) . . ? C12 C11 Cl11 124.3(2) . . ? C16 C11 Cl11 113.9(2) . . ? C13 C12 C11 119.48(19) . . ? C13 C12 H12A 120.3 . . ? C11 C12 H12A 120.3 . . ? C12 C13 C14 121.5(2) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C13 C14 C15 118.09(18) . . ? C13 C14 C17 122.8(2) . . ? C15 C14 C17 119.15(18) . . ? C16 C15 C14 121.23(17) . . ? C16 C15 H15A 119.4 . . ? C14 C15 H15A 119.4 . . ? C11 C16 C15 117.87(18) . . ? C11 C16 H16A 121.1 . . ? C15 C16 H16A 121.1 . . ? C7 C17 C14 126.9(3) . . ? C7 C17 H17A 116.5 . . ? C14 C17 H17A 116.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 Cl1 N11 O11 -174.5(11) . . . . ? C1 Cl1 N11 O11 14(4) . . . . ? O11 Cl1 N11 O12 174.5(11) . . . . ? C1 Cl1 N11 O12 -171(3) . . . . ? O11 Cl1 N11 C1 -14(4) . . . . ? O12 Cl1 N11 C1 171(3) . . . . ? O12 Cl1 O11 N11 144(7) . . . . ? C1 Cl1 O11 N11 -4.5(13) . . . . ? O12 N11 O11 Cl1 -6.4(13) . . . . ? C1 N11 O11 Cl1 173(2) . . . . ? O11 N11 O12 Cl1 3.6(7) . . . . ? C1 N11 O12 Cl1 -175.5(17) . . . . ? O11 Cl1 O12 N11 -146(6) . . . . ? C1 Cl1 O12 N11 2.7(10) . . . . ? Cl1 N11 C1 C2 -169(3) . . . . ? O11 N11 C1 C2 -178.4(7) . . . . ? O12 N11 C1 C2 0.7(8) . . . . ? Cl1 N11 C1 C6 12(3) . . . . ? O11 N11 C1 C6 3.5(10) . . . . ? O12 N11 C1 C6 -177.3(4) . . . . ? O11 N11 C1 Cl1 -9(3) . . . . ? O12 N11 C1 Cl1 170(4) . . . . ? O11 Cl1 C1 N11 168(4) . . . . ? O12 Cl1 C1 N11 -8(3) . . . . ? N11 Cl1 C1 C2 11(3) . . . . ? O11 Cl1 C1 C2 179.1(7) . . . . ? O12 Cl1 C1 C2 3.6(3) . . . . ? N11 Cl1 C1 C6 -168(3) . . . . ? O11 Cl1 C1 C6 -0.8(8) . . . . ? O12 Cl1 C1 C6 -176.3(2) . . . . ? N11 C1 C2 C3 -178.9(4) . . . . ? C6 C1 C2 C3 -0.9(3) . . . . ? Cl1 C1 C2 C3 179.2(2) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C2 C3 C4 C7 179.42(16) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C7 C4 C5 C6 -179.55(16) . . . . ? N11 C1 C6 C5 178.6(4) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? Cl1 C1 C6 C5 -179.37(19) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C3 C4 C7 C17 -4.5(4) . . . . ? C5 C4 C7 C17 175.8(2) . . . . ? O2 Cl11 N1 O1 174.5(11) . . . . ? C11 Cl11 N1 O1 -14(4) . . . . ? O1 Cl11 N1 O2 -174.5(11) . . . . ? C11 Cl11 N1 O2 171(3) . . . . ? O1 Cl11 N1 C11 14(4) . . . . ? O2 Cl11 N1 C11 -171(3) . . . . ? O2 Cl11 O1 N1 -144(7) . . . . ? C11 Cl11 O1 N1 4.5(13) . . . . ? O2 N1 O1 Cl11 6.4(13) . . . . ? C11 N1 O1 Cl11 -173(2) . . . . ? O1 N1 O2 Cl11 -3.6(7) . . . . ? C11 N1 O2 Cl11 175.5(17) . . . . ? O1 Cl11 O2 N1 146(6) . . . . ? C11 Cl11 O2 N1 -2.7(10) . . . . ? Cl11 N1 C11 C12 169(3) . . . . ? O1 N1 C11 C12 178.4(7) . . . . ? O2 N1 C11 C12 -0.7(8) . . . . ? Cl11 N1 C11 C16 -12(3) . . . . ? O1 N1 C11 C16 -3.5(10) . . . . ? O2 N1 C11 C16 177.3(4) . . . . ? O1 N1 C11 Cl11 9(3) . . . . ? O2 N1 C11 Cl11 -170(4) . . . . ? O1 Cl11 C11 N1 -168(4) . . . . ? O2 Cl11 C11 N1 8(3) . . . . ? N1 Cl11 C11 C12 -11(3) . . . . ? O1 Cl11 C11 C12 -179.1(7) . . . . ? O2 Cl11 C11 C12 -3.6(3) . . . . ? N1 Cl11 C11 C16 168(3) . . . . ? O1 Cl11 C11 C16 0.8(8) . . . . ? O2 Cl11 C11 C16 176.3(2) . . . . ? N1 C11 C12 C13 178.9(4) . . . . ? C16 C11 C12 C13 0.9(3) . . . . ? Cl11 C11 C12 C13 -179.2(2) . . . . ? C11 C12 C13 C14 -0.9(3) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? C12 C13 C14 C17 -179.42(16) . . . . ? C13 C14 C15 C16 -0.7(3) . . . . ? C17 C14 C15 C16 179.55(16) . . . . ? N1 C11 C16 C15 -178.6(4) . . . . ? C12 C11 C16 C15 -0.7(3) . . . . ? Cl11 C11 C16 C15 179.37(19) . . . . ? C14 C15 C16 C11 0.6(3) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 4.5(4) . . . . ? C15 C14 C17 C7 -175.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 27.83 _diffrn_measured_fraction_theta_full 0.878 _refine_diff_density_max 0.171 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.035 # start Validation Reply Form _vrf_SYMMG02_CNS-NO2BzI-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-NO2BzI-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.88 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:22. ; # end Validation Reply Form #===END data_CNS-NO2BzI-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761217' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9220(2) _cell_length_b 12.9245(7) _cell_length_c 12.3038(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.957(2) _cell_angle_gamma 90.00 _cell_volume 622.85(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3497 _cell_measurement_theta_min 2.287 _cell_measurement_theta_max 23.0145 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.605731 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3484 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.83 _reflns_number_total 2158 _reflns_number_gt 1124 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0824P)^2^+0.0374P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(3) _refine_ls_number_reflns 2158 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1079 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1835 _refine_ls_wR_factor_gt 0.1511 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3732(11) -0.46134(16) -0.1768(4) 0.1384(18) Uani 0.459(3) 1 d P . . N11 N 0.366(2) -0.4132(5) -0.1725(7) 0.0887(15) Uani 0.541(3) 1 d P . . O11 O 0.3203(19) -0.4992(6) -0.1293(5) 0.151(3) Uani 0.541(3) 1 d P . . O12 O 0.5050(9) -0.4078(3) -0.2624(3) 0.1231(12) Uani 0.541(3) 1 d P . . C1 C 0.2615(4) -0.32877(16) -0.12376(16) 0.0816(6) Uani 1 1 d . . . C2 C 0.3130(4) -0.2376(2) -0.17821(14) 0.0916(6) Uani 1 1 d . . . H2A H 0.4113 -0.2381 -0.2454 0.110 Uiso 1 1 calc R . . C3 C 0.2199(5) -0.14768(17) -0.13334(16) 0.0910(6) Uani 1 1 d . . . H3A H 0.2523 -0.0862 -0.1708 0.109 Uiso 1 1 calc R . . C4 C 0.0771(4) -0.14431(14) -0.03290(15) 0.0774(5) Uani 1 1 d . . . C5 C 0.0273(4) -0.23769(16) 0.02108(14) 0.0837(6) Uani 1 1 d . . . H5A H -0.0705 -0.2372 0.0884 0.100 Uiso 1 1 calc R . . C6 C 0.1204(5) -0.33064(14) -0.02365(15) 0.0855(6) Uani 1 1 d . . . H6A H 0.0889 -0.3927 0.0127 0.103 Uiso 1 1 calc R . . C7 C -0.0236(5) -0.04758(14) 0.01817(16) 0.0921(6) Uani 1 1 d . . . H7A H -0.1327 -0.0535 0.0832 0.110 Uiso 1 1 calc R . . Cl11 Cl -0.3732(11) 0.46134(16) 0.1768(4) 0.1384(18) Uani 0.541(3) 1 d P . . N1 N -0.366(2) 0.4132(5) 0.1725(7) 0.0887(15) Uani 0.459(3) 1 d P . . O1 O -0.3203(19) 0.4992(6) 0.1293(5) 0.151(3) Uani 0.459(3) 1 d P . . O2 O -0.5050(9) 0.4078(3) 0.2624(3) 0.1231(12) Uani 0.459(3) 1 d P . . C11 C -0.2615(4) 0.32877(16) 0.12376(16) 0.0816(6) Uani 1 1 d . . . C12 C -0.3130(4) 0.2376(2) 0.17821(14) 0.0916(6) Uani 1 1 d . . . H12A H -0.4113 0.2381 0.2454 0.110 Uiso 1 1 calc R . . C13 C -0.2199(5) 0.14768(17) 0.13334(16) 0.0910(6) Uani 1 1 d . . . H13A H -0.2523 0.0862 0.1708 0.109 Uiso 1 1 calc R . . C14 C -0.0771(4) 0.14431(14) 0.03290(15) 0.0774(5) Uani 1 1 d . . . C15 C -0.0273(4) 0.23769(16) -0.02108(14) 0.0837(6) Uani 1 1 d . . . H15A H 0.0705 0.2372 -0.0884 0.100 Uiso 1 1 calc R . . C16 C -0.1204(5) 0.33064(14) 0.02365(15) 0.0855(6) Uani 1 1 d . . . H16A H -0.0889 0.3927 -0.0127 0.103 Uiso 1 1 calc R . . C17 C 0.0236(5) 0.04758(14) -0.01817(16) 0.0921(6) Uani 1 1 d . . . H17A H 0.1327 0.0535 -0.0832 0.110 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1228(15) 0.124(4) 0.168(3) -0.068(3) 0.0012(16) 0.028(2) N11 0.083(3) 0.085(4) 0.098(4) -0.015(4) 0.001(3) 0.009(4) O11 0.173(4) 0.094(3) 0.191(5) 0.010(3) 0.046(3) 0.014(3) O12 0.149(3) 0.126(3) 0.097(2) -0.0241(19) 0.0394(19) 0.023(2) C1 0.0608(10) 0.0986(15) 0.0849(13) -0.0123(11) -0.0006(8) 0.0044(9) C2 0.0747(12) 0.1217(18) 0.0791(12) 0.0020(12) 0.0112(9) -0.0022(12) C3 0.0785(12) 0.1020(16) 0.0930(14) 0.0133(11) 0.0089(10) -0.0042(11) C4 0.0607(9) 0.0849(13) 0.0862(13) -0.0070(10) 0.0012(8) 0.0001(9) C5 0.0726(11) 0.1040(15) 0.0752(11) -0.0027(11) 0.0107(8) 0.0004(10) C6 0.0782(11) 0.0912(14) 0.0873(13) 0.0054(10) 0.0065(9) 0.0001(10) C7 0.0737(11) 0.1101(16) 0.0930(13) 0.0104(11) 0.0101(9) -0.0067(12) Cl11 0.1228(15) 0.124(4) 0.168(3) -0.068(3) 0.0012(16) 0.028(2) N1 0.083(3) 0.085(4) 0.098(4) -0.015(4) 0.001(3) 0.009(4) O1 0.173(4) 0.094(3) 0.191(5) 0.010(3) 0.046(3) 0.014(3) O2 0.149(3) 0.126(3) 0.097(2) -0.0241(19) 0.0394(19) 0.023(2) C11 0.0608(10) 0.0986(15) 0.0849(13) -0.0123(11) -0.0006(8) 0.0044(9) C12 0.0747(12) 0.1217(18) 0.0791(12) 0.0020(12) 0.0112(9) -0.0022(12) C13 0.0785(12) 0.1020(16) 0.0930(14) 0.0133(11) 0.0089(10) -0.0042(11) C14 0.0607(9) 0.0849(13) 0.0862(13) -0.0070(10) 0.0012(8) 0.0001(9) C15 0.0726(11) 0.1040(15) 0.0752(11) -0.0027(11) 0.0107(8) 0.0004(10) C16 0.0782(11) 0.0912(14) 0.0873(13) 0.0054(10) 0.0065(9) 0.0001(10) C17 0.0737(11) 0.1101(16) 0.0930(13) 0.0104(11) 0.0101(9) -0.0067(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.625(6) . ? Cl1 O11 0.798(6) . ? Cl1 O12 1.383(5) . ? Cl1 C1 1.893(3) . ? N11 O11 1.249(13) . ? N11 O12 1.260(9) . ? N11 C1 1.321(5) . ? C1 C2 1.375(3) . ? C1 C6 1.376(3) . ? C2 C3 1.345(3) . ? C2 H2A 0.9300 . ? C3 C4 1.384(3) . ? C3 H3A 0.9300 . ? C4 C5 1.396(3) . ? C4 C7 1.463(3) . ? C5 C6 1.379(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.325(3) . ? C7 H7A 0.9300 . ? Cl11 N1 0.625(6) . ? Cl11 O1 0.798(6) . ? Cl11 O2 1.383(5) . ? Cl11 C11 1.893(3) . ? N1 O1 1.249(13) . ? N1 O2 1.260(9) . ? N1 C11 1.321(5) . ? C11 C12 1.375(3) . ? C11 C16 1.376(3) . ? C12 C13 1.345(3) . ? C12 H12A 0.9300 . ? C13 C14 1.384(3) . ? C13 H13A 0.9300 . ? C14 C15 1.396(3) . ? C14 C17 1.463(3) . ? C15 C16 1.379(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 122.3(18) . . ? N11 Cl1 O12 65.5(11) . . ? O11 Cl1 O12 170.6(8) . . ? N11 Cl1 C1 19.6(10) . . ? O11 Cl1 C1 103.3(9) . . ? O12 Cl1 C1 84.9(2) . . ? Cl1 N11 O11 32.7(12) . . ? Cl1 N11 O12 87.7(10) . . ? O11 N11 O12 120.1(6) . . ? Cl1 N11 C1 151.3(16) . . ? O11 N11 C1 119.1(6) . . ? O12 N11 C1 120.7(7) . . ? Cl1 O11 N11 25.0(6) . . ? N11 O12 Cl1 26.8(3) . . ? N11 C1 C2 115.5(4) . . ? N11 C1 C6 122.7(4) . . ? C2 C1 C6 121.80(19) . . ? N11 C1 Cl1 9.1(5) . . ? C2 C1 Cl1 124.4(2) . . ? C6 C1 Cl1 113.8(2) . . ? C3 C2 C1 119.36(18) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 121.6(2) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 118.09(18) . . ? C3 C4 C7 122.77(19) . . ? C5 C4 C7 119.14(18) . . ? C6 C5 C4 121.13(17) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C1 C6 C5 117.97(18) . . ? C1 C6 H6A 121.0 . . ? C5 C6 H6A 121.0 . . ? C17 C7 C4 127.1(3) . . ? C17 C7 H7A 116.5 . . ? C4 C7 H7A 116.5 . . ? N1 Cl11 O1 122.3(18) . . ? N1 Cl11 O2 65.5(11) . . ? O1 Cl11 O2 170.6(8) . . ? N1 Cl11 C11 19.6(10) . . ? O1 Cl11 C11 103.3(9) . . ? O2 Cl11 C11 84.9(2) . . ? Cl11 N1 O1 32.7(12) . . ? Cl11 N1 O2 87.7(10) . . ? O1 N1 O2 120.1(6) . . ? Cl11 N1 C11 151.3(16) . . ? O1 N1 C11 119.1(6) . . ? O2 N1 C11 120.7(7) . . ? Cl11 O1 N1 25.0(6) . . ? N1 O2 Cl11 26.8(3) . . ? N1 C11 C12 115.5(4) . . ? N1 C11 C16 122.7(4) . . ? C12 C11 C16 121.80(19) . . ? N1 C11 Cl11 9.1(5) . . ? C12 C11 Cl11 124.4(2) . . ? C16 C11 Cl11 113.8(2) . . ? C13 C12 C11 119.36(18) . . ? C13 C12 H12A 120.3 . . ? C11 C12 H12A 120.3 . . ? C12 C13 C14 121.6(2) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C13 C14 C15 118.09(18) . . ? C13 C14 C17 122.77(19) . . ? C15 C14 C17 119.14(18) . . ? C16 C15 C14 121.13(17) . . ? C16 C15 H15A 119.4 . . ? C14 C15 H15A 119.4 . . ? C11 C16 C15 117.97(18) . . ? C11 C16 H16A 121.0 . . ? C15 C16 H16A 121.0 . . ? C7 C17 C14 127.1(3) . . ? C7 C17 H17A 116.5 . . ? C14 C17 H17A 116.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 Cl1 N11 O11 -174.1(11) . . . . ? C1 Cl1 N11 O11 14(4) . . . . ? O11 Cl1 N11 O12 174.1(11) . . . . ? C1 Cl1 N11 O12 -171(3) . . . . ? O11 Cl1 N11 C1 -14(4) . . . . ? O12 Cl1 N11 C1 171(3) . . . . ? O12 Cl1 O11 N11 145(6) . . . . ? C1 Cl1 O11 N11 -4.9(13) . . . . ? O12 N11 O11 Cl1 -6.8(13) . . . . ? C1 N11 O11 Cl1 172(2) . . . . ? O11 N11 O12 Cl1 3.7(7) . . . . ? C1 N11 O12 Cl1 -175.2(17) . . . . ? O11 Cl1 O12 N11 -148(6) . . . . ? C1 Cl1 O12 N11 2.9(10) . . . . ? Cl1 N11 C1 C2 -169(3) . . . . ? O11 N11 C1 C2 -178.3(7) . . . . ? O12 N11 C1 C2 0.6(8) . . . . ? Cl1 N11 C1 C6 13(3) . . . . ? O11 N11 C1 C6 3.7(10) . . . . ? O12 N11 C1 C6 -177.4(4) . . . . ? O11 N11 C1 Cl1 -9(2) . . . . ? O12 N11 C1 Cl1 170(3) . . . . ? O11 Cl1 C1 N11 167(3) . . . . ? O12 Cl1 C1 N11 -8(3) . . . . ? N11 Cl1 C1 C2 12(3) . . . . ? O11 Cl1 C1 C2 179.1(7) . . . . ? O12 Cl1 C1 C2 3.7(3) . . . . ? N11 Cl1 C1 C6 -168(3) . . . . ? O11 Cl1 C1 C6 -1.0(8) . . . . ? O12 Cl1 C1 C6 -176.3(2) . . . . ? N11 C1 C2 C3 -178.8(4) . . . . ? C6 C1 C2 C3 -0.8(3) . . . . ? Cl1 C1 C2 C3 179.2(2) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C2 C3 C4 C7 179.45(16) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C7 C4 C5 C6 -179.57(16) . . . . ? N11 C1 C6 C5 178.5(4) . . . . ? C2 C1 C6 C5 0.6(3) . . . . ? Cl1 C1 C6 C5 -179.32(19) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C3 C4 C7 C17 -4.6(4) . . . . ? C5 C4 C7 C17 175.7(2) . . . . ? O2 Cl11 N1 O1 174.1(11) . . . . ? C11 Cl11 N1 O1 -14(4) . . . . ? O1 Cl11 N1 O2 -174.1(11) . . . . ? C11 Cl11 N1 O2 171(3) . . . . ? O1 Cl11 N1 C11 14(4) . . . . ? O2 Cl11 N1 C11 -171(3) . . . . ? O2 Cl11 O1 N1 -145(6) . . . . ? C11 Cl11 O1 N1 4.9(13) . . . . ? O2 N1 O1 Cl11 6.8(13) . . . . ? C11 N1 O1 Cl11 -172(2) . . . . ? O1 N1 O2 Cl11 -3.7(7) . . . . ? C11 N1 O2 Cl11 175.2(17) . . . . ? O1 Cl11 O2 N1 148(6) . . . . ? C11 Cl11 O2 N1 -2.9(10) . . . . ? Cl11 N1 C11 C12 169(3) . . . . ? O1 N1 C11 C12 178.3(7) . . . . ? O2 N1 C11 C12 -0.6(8) . . . . ? Cl11 N1 C11 C16 -13(3) . . . . ? O1 N1 C11 C16 -3.7(10) . . . . ? O2 N1 C11 C16 177.4(4) . . . . ? O1 N1 C11 Cl11 9(2) . . . . ? O2 N1 C11 Cl11 -170(3) . . . . ? O1 Cl11 C11 N1 -167(3) . . . . ? O2 Cl11 C11 N1 8(3) . . . . ? N1 Cl11 C11 C12 -12(3) . . . . ? O1 Cl11 C11 C12 -179.1(7) . . . . ? O2 Cl11 C11 C12 -3.7(3) . . . . ? N1 Cl11 C11 C16 168(3) . . . . ? O1 Cl11 C11 C16 1.0(8) . . . . ? O2 Cl11 C11 C16 176.3(2) . . . . ? N1 C11 C12 C13 178.8(4) . . . . ? C16 C11 C12 C13 0.8(3) . . . . ? Cl11 C11 C12 C13 -179.2(2) . . . . ? C11 C12 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? C12 C13 C14 C17 -179.45(16) . . . . ? C13 C14 C15 C16 -0.6(3) . . . . ? C17 C14 C15 C16 179.57(16) . . . . ? N1 C11 C16 C15 -178.5(4) . . . . ? C12 C11 C16 C15 -0.6(3) . . . . ? Cl11 C11 C16 C15 179.32(19) . . . . ? C14 C15 C16 C11 0.6(3) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 4.6(4) . . . . ? C15 C14 C17 C7 -175.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 27.83 _diffrn_measured_fraction_theta_full 0.917 _refine_diff_density_max 0.171 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.035 # start Validation Reply Form _vrf_SYMMG02_CNS-NO2BzI-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-NO2BzI-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.92 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:22. ; # end Validation Reply Form #===END data_CNS-NO2BzII-small-P21_c _database_code_depnum_ccdc_archive 'CCDC 761218' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.91649(10) _cell_length_b 12.9357(3) _cell_length_c 12.3004(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.999(2) _cell_angle_gamma 90.00 _cell_volume 622.32(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5704 _cell_measurement_theta_min 4.7197 _cell_measurement_theta_max 31.7955 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.871457 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7100 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator synchrotron _diffrn_measurement_device_type 'Kuma 6-circle' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean 8.2896 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8093 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 26.42 _reflns_number_total 2494 _reflns_number_gt 1669 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1173P)^2^+0.0134P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(5) _refine_ls_number_reflns 2494 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.2053 _refine_ls_wR_factor_gt 0.1823 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3732(9) -0.4613(2) -0.1775(4) 0.1355(7) Uani 0.50 1 d P . . N11 N 0.364(2) -0.4152(5) -0.1717(6) 0.0935(9) Uani 0.50 1 d P . . O11 O 0.3099(18) -0.4977(5) -0.1241(5) 0.1476(14) Uani 0.50 1 d P . . O12 O 0.5025(12) -0.4110(4) -0.2609(3) 0.1239(8) Uani 0.50 1 d P . . C1 C 0.2605(6) -0.3292(2) -0.1231(2) 0.0867(4) Uani 1 1 d . . . C2 C 0.3138(6) -0.2384(2) -0.17931(19) 0.0923(5) Uani 1 1 d . . . H2A H 0.4105 -0.2395 -0.2468 0.111 Uiso 1 1 calc R . . C3 C 0.2211(3) -0.14772(11) -0.13348(11) 0.0914(4) Uani 1 1 d . . . H3A H 0.2550 -0.0863 -0.1707 0.110 Uiso 1 1 calc R . . C4 C 0.0775(3) -0.14418(9) -0.03288(10) 0.0810(4) Uani 1 1 d . . . C5 C 0.0273(3) -0.23774(10) 0.02107(10) 0.0867(4) Uani 1 1 d . . . H5A H -0.0703 -0.2371 0.0884 0.104 Uiso 1 1 calc R . . C6 C 0.1194(3) -0.33089(10) -0.02357(10) 0.0882(4) Uani 1 1 d . . . H6A H 0.0868 -0.3928 0.0128 0.106 Uiso 1 1 calc R . . C7 C -0.0245(2) -0.04736(6) 0.01824(7) 0.0892(4) Uani 1 1 d . . . H7 H -0.1350 -0.0532 0.0831 0.107 Uiso 1 1 calc R . . Cl11 Cl -0.3715(2) 0.46139(6) 0.17689(7) 0.1355(7) Uani 0.50 1 d PR . . N1 N -0.3627(2) 0.41507(6) 0.17166(7) 0.0935(9) Uani 0.50 1 d PR . . O1 O -0.3195(2) 0.49905(6) 0.12478(7) 0.1476(14) Uani 0.50 1 d PR . . O2 O -0.5030(2) 0.41050(6) 0.26123(7) 0.1239(8) Uani 0.50 1 d PR . . C11 C -0.2624(2) 0.32904(6) 0.12351(7) 0.0867(4) Uani 1 1 d R . . C12 C -0.3141(2) 0.23854(6) 0.17895(7) 0.0923(5) Uani 1 1 d R . . H12A H -0.4111 0.2395 0.2464 0.111 Uiso 1 1 calc R . . C13 C -0.2211(3) 0.14772(11) 0.13348(11) 0.0914(4) Uani 1 1 d . . . H13A H -0.2547 0.0863 0.1708 0.110 Uiso 1 1 calc R . . C14 C -0.0775(3) 0.14418(9) 0.03288(10) 0.0810(4) Uani 1 1 d . . . C15 C -0.0273(3) 0.23774(10) -0.02107(10) 0.0867(4) Uani 1 1 d . . . H15A H 0.0703 0.2371 -0.0884 0.104 Uiso 1 1 calc R . . C16 C -0.1194(3) 0.33089(10) 0.02357(10) 0.0882(4) Uani 1 1 d . . . H16A H -0.0861 0.3929 -0.0127 0.106 Uiso 1 1 calc R . . C17 C 0.0245(2) 0.04736(6) -0.01824(7) 0.0892(4) Uani 1 1 d . . . H17 H 0.1350 0.0532 -0.0831 0.107 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1260(9) 0.1223(14) 0.1581(13) -0.0594(12) 0.0061(8) 0.0257(10) N11 0.0871(16) 0.094(2) 0.098(2) -0.0186(16) -0.0009(13) 0.0118(17) O11 0.183(3) 0.0895(17) 0.175(3) 0.0143(16) 0.051(2) 0.0152(15) O12 0.1570(19) 0.1150(16) 0.1034(13) -0.0241(12) 0.0411(13) 0.0213(12) C1 0.0700(7) 0.1011(9) 0.0888(8) -0.0133(6) 0.0020(5) 0.0055(5) C2 0.0803(8) 0.1145(10) 0.0827(8) 0.0009(6) 0.0103(6) -0.0021(6) C3 0.0844(8) 0.0972(9) 0.0931(8) 0.0097(6) 0.0094(6) -0.0047(6) C4 0.0668(6) 0.0872(8) 0.0887(8) -0.0045(5) 0.0024(5) -0.0015(5) C5 0.0785(7) 0.1011(9) 0.0812(8) 0.0000(6) 0.0116(6) 0.0009(5) C6 0.0846(8) 0.0863(8) 0.0940(8) 0.0024(5) 0.0077(6) 0.0012(5) C7 0.0765(8) 0.0999(9) 0.0916(8) 0.0036(6) 0.0098(6) -0.0042(6) Cl11 0.1260(9) 0.1223(14) 0.1581(13) -0.0594(12) 0.0061(8) 0.0257(10) N1 0.0871(16) 0.094(2) 0.098(2) -0.0186(16) -0.0009(13) 0.0118(17) O1 0.183(3) 0.0895(17) 0.175(3) 0.0143(16) 0.051(2) 0.0152(15) O2 0.1570(19) 0.1150(16) 0.1034(13) -0.0241(12) 0.0411(13) 0.0213(12) C11 0.0700(7) 0.1011(9) 0.0888(8) -0.0133(6) 0.0020(5) 0.0055(5) C12 0.0803(8) 0.1145(10) 0.0827(8) 0.0009(6) 0.0103(6) -0.0021(6) C13 0.0844(8) 0.0972(9) 0.0931(8) 0.0097(6) 0.0094(6) -0.0047(6) C14 0.0668(6) 0.0872(8) 0.0887(8) -0.0045(5) 0.0024(5) -0.0015(5) C15 0.0785(7) 0.1011(9) 0.0812(8) 0.0000(6) 0.0116(6) 0.0009(5) C16 0.0846(8) 0.0863(8) 0.0940(8) 0.0024(5) 0.0077(6) 0.0012(5) C17 0.0765(8) 0.0999(9) 0.0916(8) 0.0036(6) 0.0098(6) -0.0042(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.602(6) . ? Cl1 O11 0.855(5) . ? Cl1 O12 1.337(6) . ? Cl1 C1 1.896(3) . ? N11 O11 1.239(11) . ? N11 O12 1.251(9) . ? N11 C1 1.336(7) . ? C1 C2 1.384(3) . ? C1 C6 1.370(3) . ? C2 C3 1.359(3) . ? C2 H2A 0.9300 . ? C3 C4 1.3865(18) . ? C3 H3A 0.9300 . ? C4 C5 1.3992(16) . ? C4 C7 1.4661(15) . ? C5 C6 1.3799(17) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.3223(16) . ? C7 H7 0.9300 . ? Cl11 N1 0.6038 . ? Cl11 O1 0.8387 . ? Cl11 O2 1.3530 . ? Cl11 C11 1.8905 . ? N1 O1 1.2456 . ? N1 O2 1.2582 . ? N1 C11 1.3295 . ? C11 C12 1.3752 . ? C11 C16 1.3775(15) . ? C12 C13 1.3590(14) . ? C12 H12A 0.9300 . ? C13 C14 1.3865(18) . ? C13 H13A 0.9300 . ? C14 C15 1.3992(16) . ? C14 C17 1.4661(15) . ? C15 C16 1.3799(17) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 115.5(14) . . ? N11 Cl1 O12 68.7(12) . . ? O11 Cl1 O12 173.8(6) . . ? N11 Cl1 C1 17.9(10) . . ? O11 Cl1 C1 98.2(6) . . ? O12 Cl1 C1 86.3(3) . . ? Cl1 N11 O11 38.5(10) . . ? Cl1 N11 O12 84.7(11) . . ? O11 N11 O12 123.0(6) . . ? Cl1 N11 C1 154.2(15) . . ? O11 N11 C1 116.3(6) . . ? O12 N11 C1 120.7(7) . . ? Cl1 O11 N11 26.0(5) . . ? N11 O12 Cl1 26.6(3) . . ? N11 C1 C2 115.2(4) . . ? N11 C1 C6 122.2(4) . . ? C2 C1 C6 122.6(2) . . ? N11 C1 Cl1 7.9(5) . . ? C2 C1 Cl1 123.0(2) . . ? C6 C1 Cl1 114.4(2) . . ? C3 C2 C1 118.35(19) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C2 C3 C4 121.89(15) . . ? C2 C3 H3A 119.1 . . ? C4 C3 H3A 119.1 . . ? C3 C4 C5 117.93(11) . . ? C3 C4 C7 122.91(11) . . ? C5 C4 C7 119.16(10) . . ? C6 C5 C4 121.36(11) . . ? C6 C5 H5A 119.3 . . ? C4 C5 H5A 119.3 . . ? C5 C6 C1 117.91(14) . . ? C5 C6 H6A 121.0 . . ? C1 C6 H6A 121.0 . . ? C17 C7 C4 126.76(11) . . ? C17 C7 H7 116.6 . . ? C4 C7 H7 116.6 . . ? N1 Cl11 O1 118.5 . . ? N1 Cl11 O2 68.0 . . ? O1 Cl11 O2 170.4 . . ? N1 Cl11 C11 18.0 . . ? O1 Cl11 C11 101.1 . . ? O2 Cl11 C11 85.9 . . ? Cl11 N1 O1 36.3 . . ? Cl11 N1 O2 85.6 . . ? O1 N1 O2 121.5 . . ? Cl11 N1 C11 153.9 . . ? O1 N1 C11 118.3 . . ? O2 N1 C11 120.2 . . ? Cl11 O1 N1 25.2 . . ? N1 O2 Cl11 26.4 . . ? N1 C11 C12 115.9 . . ? N1 C11 C16 121.8 . . ? C12 C11 C16 122.3 . . ? N1 C11 Cl11 8.1 . . ? C12 C11 Cl11 123.8 . . ? C16 C11 Cl11 113.8 . . ? C13 C12 C11 118.83(6) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? C12 C13 C14 121.73(11) . . ? C12 C13 H13A 119.1 . . ? C14 C13 H13A 119.1 . . ? C13 C14 C15 117.93(11) . . ? C13 C14 C17 122.91(11) . . ? C15 C14 C17 119.16(10) . . ? C16 C15 C14 121.36(11) . . ? C16 C15 H15A 119.3 . . ? C14 C15 H15A 119.3 . . ? C15 C16 C11 117.84(10) . . ? C15 C16 H16A 121.1 . . ? C11 C16 H16A 121.1 . . ? C7 C17 C14 126.76(11) . . ? C7 C17 H17 116.6 . . ? C14 C17 H17 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 Cl1 N11 O11 -175.0(8) . . . . ? C1 Cl1 N11 O11 15(4) . . . . ? O11 Cl1 N11 O12 175.0(8) . . . . ? C1 Cl1 N11 O12 -170(3) . . . . ? O11 Cl1 N11 C1 -15(4) . . . . ? O12 Cl1 N11 C1 170(3) . . . . ? O12 Cl1 O11 N11 131(7) . . . . ? C1 Cl1 O11 N11 -4.5(11) . . . . ? O12 N11 O11 Cl1 -5.9(10) . . . . ? C1 N11 O11 Cl1 173.0(18) . . . . ? O11 N11 O12 Cl1 3.7(6) . . . . ? C1 N11 O12 Cl1 -175.2(16) . . . . ? O11 Cl1 O12 N11 -133(7) . . . . ? C1 Cl1 O12 N11 2.9(10) . . . . ? Cl1 N11 C1 C2 -168(3) . . . . ? O11 N11 C1 C2 -178.0(6) . . . . ? O12 N11 C1 C2 0.9(8) . . . . ? Cl1 N11 C1 C6 14(3) . . . . ? O11 N11 C1 C6 3.5(9) . . . . ? O12 N11 C1 C6 -177.6(5) . . . . ? O11 N11 C1 Cl1 -10(3) . . . . ? O12 N11 C1 Cl1 169(4) . . . . ? O11 Cl1 C1 N11 167(3) . . . . ? O12 Cl1 C1 N11 -9(3) . . . . ? N11 Cl1 C1 C2 13(3) . . . . ? O11 Cl1 C1 C2 179.7(6) . . . . ? O12 Cl1 C1 C2 4.0(4) . . . . ? N11 Cl1 C1 C6 -167(3) . . . . ? O11 Cl1 C1 C6 -0.7(6) . . . . ? O12 Cl1 C1 C6 -176.4(3) . . . . ? N11 C1 C2 C3 -178.6(4) . . . . ? C6 C1 C2 C3 -0.1(4) . . . . ? Cl1 C1 C2 C3 179.43(19) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 -0.4(2) . . . . ? C2 C3 C4 C7 180.00(15) . . . . ? C3 C4 C5 C6 0.5(2) . . . . ? C7 C4 C5 C6 -179.90(10) . . . . ? C4 C5 C6 C1 -0.4(2) . . . . ? N11 C1 C6 C5 178.6(4) . . . . ? C2 C1 C6 C5 0.2(3) . . . . ? Cl1 C1 C6 C5 -179.38(16) . . . . ? C3 C4 C7 C17 -4.9(2) . . . . ? C5 C4 C7 C17 175.45(11) . . . . ? O2 Cl11 N1 O1 172.2 . . . . ? C11 Cl11 N1 O1 -15.7 . . . . ? O1 Cl11 N1 O2 -172.2 . . . . ? C11 Cl11 N1 O2 172.0 . . . . ? O1 Cl11 N1 C11 15.7 . . . . ? O2 Cl11 N1 C11 -172.0 . . . . ? O2 Cl11 O1 N1 -131.0 . . . . ? C11 Cl11 O1 N1 4.9 . . . . ? O2 N1 O1 Cl11 9.1 . . . . ? C11 N1 O1 Cl11 -172.2 . . . . ? O1 N1 O2 Cl11 -5.4 . . . . ? C11 N1 O2 Cl11 176.0 . . . . ? O1 Cl11 O2 N1 134.3 . . . . ? C11 Cl11 O2 N1 -2.5 . . . . ? Cl11 N1 C11 C12 169.1 . . . . ? O1 N1 C11 C12 179.6 . . . . ? O2 N1 C11 C12 -1.7 . . . . ? Cl11 N1 C11 C16 -11.61(7) . . . . ? O1 N1 C11 C16 -1.11(7) . . . . ? O2 N1 C11 C16 177.58(7) . . . . ? O1 N1 C11 Cl11 10.5 . . . . ? O2 N1 C11 Cl11 -170.8 . . . . ? O1 Cl11 C11 N1 -165.9 . . . . ? O2 Cl11 C11 N1 7.4 . . . . ? N1 Cl11 C11 C12 -11.8 . . . . ? O1 Cl11 C11 C12 -177.7 . . . . ? O2 Cl11 C11 C12 -4.4 . . . . ? N1 Cl11 C11 C16 169.22(7) . . . . ? O1 Cl11 C11 C16 3.28(7) . . . . ? O2 Cl11 C11 C16 176.61(7) . . . . ? N1 C11 C12 C13 179.19(8) . . . . ? C16 C11 C12 C13 -0.05(10) . . . . ? Cl11 C11 C12 C13 -178.99(8) . . . . ? C11 C12 C13 C14 -0.28(15) . . . . ? C12 C13 C14 C15 0.5(2) . . . . ? C12 C13 C14 C17 -179.85(8) . . . . ? C13 C14 C15 C16 -0.5(2) . . . . ? C17 C14 C15 C16 179.90(10) . . . . ? C14 C15 C16 C11 0.16(18) . . . . ? N1 C11 C16 C15 -179.08(8) . . . . ? C12 C11 C16 C15 0.11(14) . . . . ? Cl11 C11 C16 C15 179.14(9) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 4.9(2) . . . . ? C15 C14 C17 C7 -175.45(11) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.172 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.033 # start Validation Reply Form _vrf_SYMMG02_CNS-NO2BzII-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; # end Validation Reply Form #===END data_CNS-NO2BzII-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761219' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.91649(10) _cell_length_b 12.9357(3) _cell_length_c 12.3004(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.999(2) _cell_angle_gamma 90.00 _cell_volume 622.32(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5704 _cell_measurement_theta_min 4.7197 _cell_measurement_theta_max 31.7955 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.871457 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7100 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator synchrotron _diffrn_measurement_device_type 'Kuma 6-circle' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean 8.2896 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8093 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 26.42 _reflns_number_total 2494 _reflns_number_gt 1669 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1173P)^2^+0.0134P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(2) _refine_ls_number_reflns 2494 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.2016 _refine_ls_wR_factor_gt 0.1777 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3725(10) -0.4614(2) -0.1773(3) 0.1360(7) Uani 0.479(2) 1 d P . . N11 N 0.3633(18) -0.4155(5) -0.1715(5) 0.0930(9) Uani 0.521(2) 1 d P . . O11 O 0.3115(17) -0.4979(4) -0.1250(4) 0.1491(14) Uani 0.521(2) 1 d P . . O12 O 0.5029(12) -0.4107(3) -0.2611(3) 0.1241(8) Uani 0.521(2) 1 d P . . C1 C 0.2612(6) -0.3292(2) -0.12345(18) 0.0867(4) Uani 1 1 d . . . C2 C 0.3136(6) -0.2383(2) -0.17921(18) 0.0922(4) Uani 1 1 d . . . H2A H 0.4101 -0.2392 -0.2467 0.111 Uiso 1 1 calc R . . C3 C 0.2212(3) -0.14773(10) -0.13350(11) 0.0914(4) Uani 1 1 d . . . H3A H 0.2553 -0.0863 -0.1707 0.110 Uiso 1 1 calc R . . C4 C 0.0774(3) -0.14418(8) -0.03289(10) 0.0809(4) Uani 1 1 d . . . C5 C 0.0273(3) -0.23776(9) 0.02099(9) 0.0866(4) Uani 1 1 d . . . H5A H -0.0702 -0.2372 0.0883 0.104 Uiso 1 1 calc R . . C6 C 0.1193(3) -0.33085(9) -0.02354(10) 0.0881(4) Uani 1 1 d . . . H6A H 0.0865 -0.3928 0.0128 0.106 Uiso 1 1 calc R . . C7 C -0.0245(2) -0.04736(6) 0.01819(7) 0.0890(4) Uani 1 1 d . . . H7 H -0.1352 -0.0532 0.0830 0.107 Uiso 1 1 calc R . . Cl11 Cl -0.3715(2) 0.46139(6) 0.17685(7) 0.1360(7) Uani 0.521(2) 1 d PR . . N1 N -0.3627(2) 0.41508(6) 0.17161(7) 0.0930(9) Uani 0.479(2) 1 d PR . . O1 O -0.3195(2) 0.49906(6) 0.12473(7) 0.1491(14) Uani 0.479(2) 1 d PR . . O2 O -0.5030(2) 0.41051(6) 0.26119(7) 0.1241(8) Uani 0.479(2) 1 d PR . . C11 C -0.2624(2) 0.32905(6) 0.12347(7) 0.0867(4) Uani 1 1 d R . . C12 C -0.3142(2) 0.23855(6) 0.17891(7) 0.0922(4) Uani 1 1 d R . . H12A H -0.4111 0.2395 0.2463 0.111 Uiso 1 1 calc R . . C13 C -0.2212(3) 0.14773(10) 0.13350(11) 0.0914(4) Uani 1 1 d . . . H13A H -0.2549 0.0864 0.1708 0.110 Uiso 1 1 calc R . . C14 C -0.0774(3) 0.14418(8) 0.03289(10) 0.0809(4) Uani 1 1 d . . . C15 C -0.0273(3) 0.23776(9) -0.02099(9) 0.0866(4) Uani 1 1 d . . . H15A H 0.0702 0.2372 -0.0883 0.104 Uiso 1 1 calc R . . C16 C -0.1193(3) 0.33085(9) 0.02354(10) 0.0881(4) Uani 1 1 d . . . H16A H -0.0859 0.3928 -0.0127 0.106 Uiso 1 1 calc R . . C17 C 0.0245(2) 0.04736(6) -0.01819(7) 0.0890(4) Uani 1 1 d . . . H17 H 0.1352 0.0532 -0.0830 0.107 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1262(8) 0.1222(13) 0.1595(13) -0.0600(12) 0.0055(8) 0.0261(9) N11 0.0867(16) 0.094(2) 0.098(2) -0.0178(15) -0.0009(13) 0.0109(16) O11 0.184(3) 0.0895(16) 0.178(3) 0.0152(16) 0.050(2) 0.0152(15) O12 0.1564(19) 0.1154(16) 0.1041(13) -0.0240(11) 0.0412(13) 0.0212(12) C1 0.0700(7) 0.1011(9) 0.0888(8) -0.0136(6) 0.0018(5) 0.0056(5) C2 0.0801(8) 0.1146(10) 0.0825(8) 0.0012(6) 0.0107(6) -0.0022(6) C3 0.0844(8) 0.0974(8) 0.0929(8) 0.0096(6) 0.0094(6) -0.0046(6) C4 0.0667(6) 0.0874(7) 0.0885(7) -0.0042(5) 0.0025(5) -0.0016(5) C5 0.0784(7) 0.1012(9) 0.0811(7) 0.0001(5) 0.0118(6) 0.0010(5) C6 0.0846(8) 0.0864(8) 0.0937(8) 0.0025(5) 0.0077(6) 0.0010(5) C7 0.0764(7) 0.1000(9) 0.0913(8) 0.0038(6) 0.0098(6) -0.0042(6) Cl11 0.1262(8) 0.1222(13) 0.1595(13) -0.0600(12) 0.0055(8) 0.0261(9) N1 0.0867(16) 0.094(2) 0.098(2) -0.0178(15) -0.0009(13) 0.0109(16) O1 0.184(3) 0.0895(16) 0.178(3) 0.0152(16) 0.050(2) 0.0152(15) O2 0.1564(19) 0.1154(16) 0.1041(13) -0.0240(11) 0.0412(13) 0.0212(12) C11 0.0700(7) 0.1011(9) 0.0888(8) -0.0136(6) 0.0018(5) 0.0056(5) C12 0.0801(8) 0.1146(10) 0.0825(8) 0.0012(6) 0.0107(6) -0.0022(6) C13 0.0844(8) 0.0974(8) 0.0929(8) 0.0096(6) 0.0094(6) -0.0046(6) C14 0.0667(6) 0.0874(7) 0.0885(7) -0.0042(5) 0.0025(5) -0.0016(5) C15 0.0784(7) 0.1012(9) 0.0811(7) 0.0001(5) 0.0118(6) 0.0010(5) C16 0.0846(8) 0.0864(8) 0.0937(8) 0.0025(5) 0.0077(6) 0.0010(5) C17 0.0764(7) 0.1000(9) 0.0913(8) 0.0038(6) 0.0098(6) -0.0042(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.599(6) . ? Cl1 O11 0.842(5) . ? Cl1 O12 1.345(6) . ? Cl1 C1 1.894(3) . ? N11 O11 1.231(10) . ? N11 O12 1.257(8) . ? N11 C1 1.335(6) . ? C1 C2 1.381(3) . ? C1 C6 1.375(3) . ? C2 C3 1.357(3) . ? C2 H2A 0.9300 . ? C3 C4 1.3870(18) . ? C3 H3A 0.9300 . ? C4 C5 1.3989(16) . ? C4 C7 1.4659(14) . ? C5 C6 1.3786(17) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.3218(16) . ? C7 H7 0.9300 . ? Cl11 N1 0.6038 . ? Cl11 O1 0.8387 . ? Cl11 O2 1.3530 . ? Cl11 C11 1.8905 . ? N1 O1 1.2456 . ? N1 O2 1.2582 . ? N1 C11 1.3295 . ? C11 C12 1.3752 . ? C11 C16 1.3775(15) . ? C12 C13 1.3587(14) . ? C12 H12A 0.9300 . ? C13 C14 1.3870(18) . ? C13 H13A 0.9300 . ? C14 C15 1.3989(16) . ? C14 C17 1.4659(14) . ? C15 C16 1.3786(17) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 116.3(13) . . ? N11 Cl1 O12 68.7(11) . . ? O11 Cl1 O12 173.1(6) . . ? N11 Cl1 C1 17.6(9) . . ? O11 Cl1 C1 99.2(6) . . ? O12 Cl1 C1 86.1(3) . . ? Cl1 N11 O11 37.9(10) . . ? Cl1 N11 O12 85.0(10) . . ? O11 N11 O12 122.7(6) . . ? Cl1 N11 C1 154.6(14) . . ? O11 N11 C1 117.3(6) . . ? O12 N11 C1 120.1(6) . . ? Cl1 O11 N11 25.9(4) . . ? N11 O12 Cl1 26.3(3) . . ? N11 C1 C2 115.9(4) . . ? N11 C1 C6 121.8(4) . . ? C2 C1 C6 122.3(2) . . ? N11 C1 Cl1 7.8(4) . . ? C2 C1 Cl1 123.5(2) . . ? C6 C1 Cl1 114.2(2) . . ? C3 C2 C1 118.63(18) . . ? C3 C2 H2A 120.7 . . ? C1 C2 H2A 120.7 . . ? C2 C3 C4 121.86(14) . . ? C2 C3 H3A 119.1 . . ? C4 C3 H3A 119.1 . . ? C3 C4 C5 117.88(10) . . ? C3 C4 C7 122.90(11) . . ? C5 C4 C7 119.22(10) . . ? C6 C5 C4 121.44(11) . . ? C6 C5 H5A 119.3 . . ? C4 C5 H5A 119.3 . . ? C5 C6 C1 117.88(14) . . ? C5 C6 H6A 121.1 . . ? C1 C6 H6A 121.1 . . ? C17 C7 C4 126.81(10) . . ? C17 C7 H7 116.6 . . ? C4 C7 H7 116.6 . . ? N1 Cl11 O1 118.5 . . ? N1 Cl11 O2 68.0 . . ? O1 Cl11 O2 170.4 . . ? N1 Cl11 C11 18.0 . . ? O1 Cl11 C11 101.1 . . ? O2 Cl11 C11 85.9 . . ? Cl11 N1 O1 36.3 . . ? Cl11 N1 O2 85.6 . . ? O1 N1 O2 121.5 . . ? Cl11 N1 C11 153.9 . . ? O1 N1 C11 118.3 . . ? O2 N1 C11 120.2 . . ? Cl11 O1 N1 25.2 . . ? N1 O2 Cl11 26.4 . . ? N1 C11 C12 115.9 . . ? N1 C11 C16 121.8 . . ? C12 C11 C16 122.3 . . ? N1 C11 Cl11 8.1 . . ? C12 C11 Cl11 123.8 . . ? C16 C11 Cl11 113.9 . . ? C13 C12 C11 118.86(6) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? C12 C13 C14 121.71(11) . . ? C12 C13 H13A 119.1 . . ? C14 C13 H13A 119.1 . . ? C13 C14 C15 117.88(10) . . ? C13 C14 C17 122.90(11) . . ? C15 C14 C17 119.22(10) . . ? C16 C15 C14 121.44(11) . . ? C16 C15 H15A 119.3 . . ? C14 C15 H15A 119.3 . . ? C15 C16 C11 117.83(9) . . ? C15 C16 H16A 121.1 . . ? C11 C16 H16A 121.1 . . ? C7 C17 C14 126.81(10) . . ? C7 C17 H17 116.6 . . ? C14 C17 H17 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 Cl1 N11 O11 -174.7(8) . . . . ? C1 Cl1 N11 O11 15(3) . . . . ? O11 Cl1 N11 O12 174.7(8) . . . . ? C1 Cl1 N11 O12 -171(3) . . . . ? O11 Cl1 N11 C1 -15(3) . . . . ? O12 Cl1 N11 C1 171(3) . . . . ? O12 Cl1 O11 N11 134(6) . . . . ? C1 Cl1 O11 N11 -4.4(11) . . . . ? O12 N11 O11 Cl1 -6.3(10) . . . . ? C1 N11 O11 Cl1 173.0(17) . . . . ? O11 N11 O12 Cl1 3.9(6) . . . . ? C1 N11 O12 Cl1 -175.4(15) . . . . ? O11 Cl1 O12 N11 -136(6) . . . . ? C1 Cl1 O12 N11 2.8(9) . . . . ? Cl1 N11 C1 C2 -168(3) . . . . ? O11 N11 C1 C2 -178.1(6) . . . . ? O12 N11 C1 C2 1.2(8) . . . . ? Cl1 N11 C1 C6 13(3) . . . . ? O11 N11 C1 C6 3.2(9) . . . . ? O12 N11 C1 C6 -177.5(4) . . . . ? O11 N11 C1 Cl1 -10(2) . . . . ? O12 N11 C1 Cl1 169(3) . . . . ? O11 Cl1 C1 N11 167(3) . . . . ? O12 Cl1 C1 N11 -9(3) . . . . ? N11 Cl1 C1 C2 13(3) . . . . ? O11 Cl1 C1 C2 179.6(6) . . . . ? O12 Cl1 C1 C2 4.2(3) . . . . ? N11 Cl1 C1 C6 -168(3) . . . . ? O11 Cl1 C1 C6 -1.0(6) . . . . ? O12 Cl1 C1 C6 -176.4(3) . . . . ? N11 C1 C2 C3 -178.7(4) . . . . ? C6 C1 C2 C3 0.0(3) . . . . ? Cl1 C1 C2 C3 179.34(19) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 -0.3(2) . . . . ? C2 C3 C4 C7 -179.99(14) . . . . ? C3 C4 C5 C6 0.43(19) . . . . ? C7 C4 C5 C6 -179.89(10) . . . . ? C4 C5 C6 C1 -0.3(2) . . . . ? N11 C1 C6 C5 178.8(4) . . . . ? C2 C1 C6 C5 0.1(3) . . . . ? Cl1 C1 C6 C5 -179.30(16) . . . . ? C3 C4 C7 C17 -4.94(19) . . . . ? C5 C4 C7 C17 175.40(11) . . . . ? O2 Cl11 N1 O1 172.2 . . . . ? C11 Cl11 N1 O1 -15.7 . . . . ? O1 Cl11 N1 O2 -172.2 . . . . ? C11 Cl11 N1 O2 172.0 . . . . ? O1 Cl11 N1 C11 15.7 . . . . ? O2 Cl11 N1 C11 -172.0 . . . . ? O2 Cl11 O1 N1 -131.0 . . . . ? C11 Cl11 O1 N1 4.9 . . . . ? O2 N1 O1 Cl11 9.1 . . . . ? C11 N1 O1 Cl11 -172.2 . . . . ? O1 N1 O2 Cl11 -5.4 . . . . ? C11 N1 O2 Cl11 176.0 . . . . ? O1 Cl11 O2 N1 134.3 . . . . ? C11 Cl11 O2 N1 -2.5 . . . . ? Cl11 N1 C11 C12 169.1 . . . . ? O1 N1 C11 C12 179.6 . . . . ? O2 N1 C11 C12 -1.7 . . . . ? Cl11 N1 C11 C16 -11.59(7) . . . . ? O1 N1 C11 C16 -1.09(7) . . . . ? O2 N1 C11 C16 177.60(7) . . . . ? O1 N1 C11 Cl11 10.5 . . . . ? O2 N1 C11 Cl11 -170.8 . . . . ? O1 Cl11 C11 N1 -165.9 . . . . ? O2 Cl11 C11 N1 7.4 . . . . ? N1 Cl11 C11 C12 -11.8 . . . . ? O1 Cl11 C11 C12 -177.7 . . . . ? O2 Cl11 C11 C12 -4.4 . . . . ? N1 Cl11 C11 C16 169.24(7) . . . . ? O1 Cl11 C11 C16 3.30(7) . . . . ? O2 Cl11 C11 C16 176.63(7) . . . . ? N1 C11 C12 C13 179.19(7) . . . . ? C16 C11 C12 C13 -0.06(10) . . . . ? Cl11 C11 C12 C13 -178.98(7) . . . . ? C11 C12 C13 C14 -0.26(15) . . . . ? C12 C13 C14 C15 0.50(19) . . . . ? C12 C13 C14 C17 -179.84(8) . . . . ? C13 C14 C15 C16 -0.43(19) . . . . ? C17 C14 C15 C16 179.89(10) . . . . ? C14 C15 C16 C11 0.13(18) . . . . ? N1 C11 C16 C15 -179.09(8) . . . . ? C12 C11 C16 C15 0.13(14) . . . . ? Cl11 C11 C16 C15 179.14(9) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 4.94(19) . . . . ? C15 C14 C17 C7 -175.40(11) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.174 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.034 # start Validation Reply Form _vrf_SYMMG02_CNS-NO2BzII-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; # end Validation Reply Form #===END data_CNS-Me2CO-small-P21/c _database_code_depnum_ccdc_archive 'CCDC 761220' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall 'P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9118(2) _cell_length_b 12.9470(5) _cell_length_c 12.2260(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.191(2) _cell_angle_gamma 90.00 _cell_volume 618.24(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3476 _cell_measurement_theta_min 3.147 _cell_measurement_theta_max 25.776 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.301 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.784465 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3455 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.76 _reflns_number_total 1817 _reflns_number_gt 1248 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+0.0652P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 1817 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3706(7) -0.46100(11) -0.1754(3) 0.1152(10) Uani 0.50 1 d P . . N11 N 0.3624(16) -0.4157(3) -0.1725(6) 0.0810(12) Uani 0.50 1 d P . . O11 O 0.3173(13) -0.4979(4) -0.1231(3) 0.1320(16) Uani 0.50 1 d P . . O12 O 0.4982(7) -0.4126(2) -0.2585(2) 0.1149(9) Uani 0.50 1 d P . . C1 C 0.2612(3) -0.32955(13) -0.12308(12) 0.0751(4) Uani 1 1 d . . . C2 C 0.3149(3) -0.23918(15) -0.17905(11) 0.0810(5) Uani 1 1 d . . . H2A H 0.4129 -0.2407 -0.2466 0.097 Uiso 1 1 calc R . . C3 C 0.2228(4) -0.14736(13) -0.13443(11) 0.0769(4) Uani 1 1 d . . . H3A H 0.2572 -0.0864 -0.1725 0.092 Uiso 1 1 calc R . . C4 C 0.0782(3) -0.14324(11) -0.03290(10) 0.0662(4) Uani 1 1 d . . . C5 C 0.0283(3) -0.23605(12) 0.02053(11) 0.0731(4) Uani 1 1 d . . . H5A H -0.0699 -0.2351 0.0881 0.088 Uiso 1 1 calc R . . C6 C 0.1186(4) -0.32920(12) -0.02268(12) 0.0779(4) Uani 1 1 d . . . H6A H 0.0843 -0.3905 0.0148 0.094 Uiso 1 1 calc R . . C7 C -0.0243(3) -0.04653(11) 0.01832(11) 0.0726(4) Uani 1 1 d . . . H7A H -0.1349 -0.0522 0.0834 0.087 Uiso 1 1 calc R . . Cl11 Cl -0.3706(7) 0.46100(11) 0.1754(3) 0.1152(10) Uani 0.50 1 d P . . N1 N -0.3624(16) 0.4157(3) 0.1725(6) 0.0810(12) Uani 0.50 1 d P . . O1 O -0.3173(13) 0.4979(4) 0.1231(3) 0.1320(16) Uani 0.50 1 d P . . O2 O -0.4982(7) 0.4126(2) 0.2585(2) 0.1149(9) Uani 0.50 1 d P . . C11 C -0.2612(3) 0.32955(13) 0.12308(12) 0.0751(4) Uani 1 1 d . . . C12 C -0.3149(3) 0.23918(15) 0.17905(11) 0.0810(5) Uani 1 1 d . . . H12A H -0.4129 0.2407 0.2466 0.097 Uiso 1 1 calc R . . C13 C -0.2228(4) 0.14736(13) 0.13443(11) 0.0769(4) Uani 1 1 d . . . H13A H -0.2572 0.0864 0.1725 0.092 Uiso 1 1 calc R . . C14 C -0.0782(3) 0.14324(11) 0.03290(10) 0.0662(4) Uani 1 1 d . . . C15 C -0.0283(3) 0.23605(12) -0.02053(11) 0.0731(4) Uani 1 1 d . . . H15A H 0.0699 0.2351 -0.0881 0.088 Uiso 1 1 calc R . . C16 C -0.1186(4) 0.32920(12) 0.02268(12) 0.0779(4) Uani 1 1 d . . . H16A H -0.0843 0.3905 -0.0148 0.094 Uiso 1 1 calc R . . C17 C 0.0243(3) 0.04653(11) -0.01832(11) 0.0726(4) Uani 1 1 d . . . H17A H 0.1349 0.0522 -0.0834 0.087 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1153(10) 0.094(2) 0.1353(17) -0.0461(19) 0.0033(10) 0.0252(15) N11 0.078(2) 0.066(3) 0.099(3) -0.005(3) -0.0014(19) 0.008(3) O11 0.173(3) 0.080(2) 0.147(3) 0.012(2) 0.042(2) 0.014(2) O12 0.153(2) 0.0948(19) 0.0999(17) -0.0259(16) 0.0320(16) 0.0199(16) C1 0.0598(8) 0.0877(11) 0.0771(9) -0.0144(8) -0.0013(6) 0.0047(7) C2 0.0693(9) 0.1078(13) 0.0666(9) -0.0041(8) 0.0093(7) -0.0011(8) C3 0.0717(9) 0.0843(11) 0.0750(9) 0.0075(8) 0.0077(7) -0.0036(7) C4 0.0525(7) 0.0785(10) 0.0674(8) -0.0032(7) 0.0010(6) -0.0013(6) C5 0.0697(8) 0.0833(11) 0.0669(8) 0.0002(7) 0.0088(6) -0.0003(7) C6 0.0743(9) 0.0796(11) 0.0798(9) 0.0026(8) 0.0034(7) 0.0023(8) C7 0.0620(8) 0.0841(10) 0.0721(8) 0.0042(7) 0.0076(6) -0.0033(7) Cl11 0.1153(10) 0.094(2) 0.1353(17) -0.0461(19) 0.0033(10) 0.0252(15) N1 0.078(2) 0.066(3) 0.099(3) -0.005(3) -0.0014(19) 0.008(3) O1 0.173(3) 0.080(2) 0.147(3) 0.012(2) 0.042(2) 0.014(2) O2 0.153(2) 0.0948(19) 0.0999(17) -0.0259(16) 0.0320(16) 0.0199(16) C11 0.0598(8) 0.0877(11) 0.0771(9) -0.0144(8) -0.0013(6) 0.0047(7) C12 0.0693(9) 0.1078(13) 0.0666(9) -0.0041(8) 0.0093(7) -0.0011(8) C13 0.0717(9) 0.0843(11) 0.0750(9) 0.0075(8) 0.0077(7) -0.0036(7) C14 0.0525(7) 0.0785(10) 0.0674(8) -0.0032(7) 0.0010(6) -0.0013(6) C15 0.0697(8) 0.0833(11) 0.0669(8) 0.0002(7) 0.0088(6) -0.0003(7) C16 0.0743(9) 0.0796(11) 0.0798(9) 0.0026(8) 0.0034(7) 0.0023(8) C17 0.0620(8) 0.0841(10) 0.0721(8) 0.0042(7) 0.0076(6) -0.0033(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.588(4) . ? Cl1 O11 0.833(4) . ? Cl1 O12 1.316(4) . ? Cl1 C1 1.876(2) . ? N11 O12 1.204(7) . ? N11 O11 1.240(9) . ? N11 C1 1.339(4) . ? C1 C6 1.376(2) . ? C1 C2 1.377(2) . ? C2 C3 1.365(2) . ? C2 H2A 0.9300 . ? C3 C4 1.394(2) . ? C3 H3A 0.9300 . ? C4 C5 1.3867(19) . ? C4 C7 1.466(2) . ? C5 C6 1.3708(19) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.303(3) . ? C7 H7A 0.9300 . ? Cl11 N1 0.588(4) . ? Cl11 O1 0.833(4) . ? Cl11 O2 1.316(4) . ? Cl11 C11 1.876(2) . ? N1 O2 1.204(7) . ? N1 O1 1.240(9) . ? N1 C11 1.339(4) . ? C11 C16 1.376(2) . ? C11 C12 1.377(2) . ? C12 C13 1.365(2) . ? C12 H12A 0.9300 . ? C13 C14 1.394(2) . ? C13 H13A 0.9300 . ? C14 C15 1.3867(19) . ? C14 C17 1.466(2) . ? C15 C16 1.3708(19) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 120.6(13) . . ? N11 Cl1 O12 66.1(9) . . ? O11 Cl1 O12 170.7(5) . . ? N11 Cl1 C1 20.2(9) . . ? O11 Cl1 C1 100.8(5) . . ? O12 Cl1 C1 86.23(16) . . ? Cl1 N11 O12 87.3(9) . . ? Cl1 N11 O11 35.3(9) . . ? O12 N11 O11 122.4(4) . . ? Cl1 N11 C1 151.1(13) . . ? O12 N11 C1 121.4(5) . . ? O11 N11 C1 116.2(5) . . ? Cl1 O11 N11 24.1(4) . . ? N11 O12 Cl1 26.5(2) . . ? N11 C1 C6 123.3(3) . . ? N11 C1 C2 115.3(3) . . ? C6 C1 C2 121.38(15) . . ? N11 C1 Cl1 8.7(4) . . ? C6 C1 Cl1 114.73(17) . . ? C2 C1 Cl1 123.89(16) . . ? C3 C2 C1 119.38(14) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 121.24(16) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C5 C4 C3 117.46(14) . . ? C5 C4 C7 119.34(12) . . ? C3 C4 C7 123.20(14) . . ? C6 C5 C4 122.33(13) . . ? C6 C5 H5A 118.8 . . ? C4 C5 H5A 118.8 . . ? C5 C6 C1 118.20(15) . . ? C5 C6 H6A 120.9 . . ? C1 C6 H6A 120.9 . . ? C17 C7 C4 126.47(18) . . ? C17 C7 H7A 116.8 . . ? C4 C7 H7A 116.8 . . ? N1 Cl11 O1 120.6(13) . . ? N1 Cl11 O2 66.1(9) . . ? O1 Cl11 O2 170.7(5) . . ? N1 Cl11 C11 20.2(9) . . ? O1 Cl11 C11 100.8(5) . . ? O2 Cl11 C11 86.23(16) . . ? Cl11 N1 O2 87.3(9) . . ? Cl11 N1 O1 35.3(9) . . ? O2 N1 O1 122.4(4) . . ? Cl11 N1 C11 151.1(13) . . ? O2 N1 C11 121.4(5) . . ? O1 N1 C11 116.2(5) . . ? Cl11 O1 N1 24.1(4) . . ? N1 O2 Cl11 26.5(2) . . ? N1 C11 C16 123.3(3) . . ? N1 C11 C12 115.3(3) . . ? C16 C11 C12 121.38(15) . . ? N1 C11 Cl11 8.7(4) . . ? C16 C11 Cl11 114.73(17) . . ? C12 C11 Cl11 123.89(16) . . ? C13 C12 C11 119.38(14) . . ? C13 C12 H12A 120.3 . . ? C11 C12 H12A 120.3 . . ? C12 C13 C14 121.24(16) . . ? C12 C13 H13A 119.4 . . ? C14 C13 H13A 119.4 . . ? C15 C14 C13 117.46(14) . . ? C15 C14 C17 119.34(12) . . ? C13 C14 C17 123.20(14) . . ? C16 C15 C14 122.33(13) . . ? C16 C15 H15A 118.8 . . ? C14 C15 H15A 118.8 . . ? C15 C16 C11 118.20(15) . . ? C15 C16 H16A 120.9 . . ? C11 C16 H16A 120.9 . . ? C7 C17 C14 126.47(18) . . ? C7 C17 H17A 116.8 . . ? C14 C17 H17A 116.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.8(7) . . . . ? C1 Cl1 N11 O12 -175(2) . . . . ? O12 Cl1 N11 O11 -172.8(7) . . . . ? C1 Cl1 N11 O11 12(3) . . . . ? O11 Cl1 N11 C1 -12(3) . . . . ? O12 Cl1 N11 C1 175(2) . . . . ? O12 Cl1 O11 N11 135(4) . . . . ? C1 Cl1 O11 N11 -4.2(10) . . . . ? O12 N11 O11 Cl1 -8.5(8) . . . . ? C1 N11 O11 Cl1 173.5(15) . . . . ? O11 N11 O12 Cl1 4.9(5) . . . . ? C1 N11 O12 Cl1 -177.2(13) . . . . ? O11 Cl1 O12 N11 -138(4) . . . . ? C1 Cl1 O12 N11 1.7(8) . . . . ? Cl1 N11 C1 C6 9(2) . . . . ? O12 N11 C1 C6 -177.1(4) . . . . ? O11 N11 C1 C6 0.8(8) . . . . ? Cl1 N11 C1 C2 -172(2) . . . . ? O12 N11 C1 C2 1.8(7) . . . . ? O11 N11 C1 C2 179.8(5) . . . . ? O12 N11 C1 Cl1 174(3) . . . . ? O11 N11 C1 Cl1 -7.8(18) . . . . ? O11 Cl1 C1 N11 169(2) . . . . ? O12 Cl1 C1 N11 -5(2) . . . . ? N11 Cl1 C1 C6 -172(2) . . . . ? O11 Cl1 C1 C6 -2.7(5) . . . . ? O12 Cl1 C1 C6 -176.58(17) . . . . ? N11 Cl1 C1 C2 8(2) . . . . ? O11 Cl1 C1 C2 177.6(4) . . . . ? O12 Cl1 C1 C2 3.7(3) . . . . ? N11 C1 C2 C3 -179.4(3) . . . . ? C6 C1 C2 C3 -0.4(2) . . . . ? Cl1 C1 C2 C3 179.26(15) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C2 C3 C4 C7 179.91(12) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C7 C4 C5 C6 -179.93(12) . . . . ? C4 C5 C6 C1 -0.5(2) . . . . ? N11 C1 C6 C5 179.2(3) . . . . ? C2 C1 C6 C5 0.4(2) . . . . ? Cl1 C1 C6 C5 -179.34(14) . . . . ? C5 C4 C7 C17 175.65(17) . . . . ? C3 C4 C7 C17 -4.9(3) . . . . ? O1 Cl11 N1 O2 -172.8(7) . . . . ? C11 Cl11 N1 O2 175(2) . . . . ? O2 Cl11 N1 O1 172.8(7) . . . . ? C11 Cl11 N1 O1 -12(3) . . . . ? O1 Cl11 N1 C11 12(3) . . . . ? O2 Cl11 N1 C11 -175(2) . . . . ? O2 Cl11 O1 N1 -135(4) . . . . ? C11 Cl11 O1 N1 4.2(10) . . . . ? O2 N1 O1 Cl11 8.5(8) . . . . ? C11 N1 O1 Cl11 -173.5(15) . . . . ? O1 N1 O2 Cl11 -4.9(5) . . . . ? C11 N1 O2 Cl11 177.2(13) . . . . ? O1 Cl11 O2 N1 138(4) . . . . ? C11 Cl11 O2 N1 -1.7(8) . . . . ? Cl11 N1 C11 C16 -9(2) . . . . ? O2 N1 C11 C16 177.1(4) . . . . ? O1 N1 C11 C16 -0.8(8) . . . . ? Cl11 N1 C11 C12 172(2) . . . . ? O2 N1 C11 C12 -1.8(7) . . . . ? O1 N1 C11 C12 -179.8(5) . . . . ? O2 N1 C11 Cl11 -174(3) . . . . ? O1 N1 C11 Cl11 7.8(18) . . . . ? O1 Cl11 C11 N1 -169(2) . . . . ? O2 Cl11 C11 N1 5(2) . . . . ? N1 Cl11 C11 C16 172(2) . . . . ? O1 Cl11 C11 C16 2.7(5) . . . . ? O2 Cl11 C11 C16 176.58(17) . . . . ? N1 Cl11 C11 C12 -8(2) . . . . ? O1 Cl11 C11 C12 -177.6(4) . . . . ? O2 Cl11 C11 C12 -3.7(3) . . . . ? N1 C11 C12 C13 179.4(3) . . . . ? C16 C11 C12 C13 0.4(2) . . . . ? Cl11 C11 C12 C13 -179.26(15) . . . . ? C11 C12 C13 C14 -0.6(2) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C12 C13 C14 C17 -179.91(12) . . . . ? C13 C14 C15 C16 -0.6(2) . . . . ? C17 C14 C15 C16 179.93(12) . . . . ? C14 C15 C16 C11 0.5(2) . . . . ? N1 C11 C16 C15 -179.2(3) . . . . ? C12 C11 C16 C15 -0.4(2) . . . . ? Cl11 C11 C16 C15 179.34(14) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.65(17) . . . . ? C13 C14 C17 C7 4.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.883 _diffrn_reflns_theta_full 27.76 _diffrn_measured_fraction_theta_full 0.883 _refine_diff_density_max 0.086 _refine_diff_density_min -0.127 _refine_diff_density_rms 0.034 # start Validation Reply Form _vrf_SYMMG02_CNS-Me2CO-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-Me2CO-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.88 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:18. ; # end Validation Reply Form #===END data_CNS-Me2CO-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761221' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9118(2) _cell_length_b 12.9470(5) _cell_length_c 12.2260(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.191(2) _cell_angle_gamma 90.00 _cell_volume 618.24(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3476 _cell_measurement_theta_min 3.147 _cell_measurement_theta_max 25.776 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.301 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.784465 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3455 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.76 _reflns_number_total 1817 _reflns_number_gt 1248 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+0.0652P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(3) _refine_ls_number_reflns 1817 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1064 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3708(7) -0.46091(10) -0.1755(2) 0.1153(9) Uani 0.4552(19) 1 d P . . N11 N 0.3624(15) -0.4158(3) -0.1722(5) 0.0817(11) Uani 0.5448(19) 1 d P . . O11 O 0.3171(12) -0.4976(3) -0.1232(3) 0.1313(15) Uani 0.5448(19) 1 d P . . O12 O 0.4981(7) -0.4128(2) -0.2584(2) 0.1142(8) Uani 0.5448(19) 1 d P . . C1 C 0.2614(3) -0.32955(12) -0.12310(11) 0.0751(4) Uani 1 1 d . . . C2 C 0.3149(3) -0.23910(14) -0.17913(10) 0.0809(4) Uani 1 1 d . . . H2A H 0.4129 -0.2406 -0.2467 0.097 Uiso 1 1 calc R . . C3 C 0.2227(3) -0.14743(12) -0.13445(11) 0.0771(4) Uani 1 1 d . . . H3A H 0.2570 -0.0865 -0.1725 0.093 Uiso 1 1 calc R . . C4 C 0.0782(3) -0.14322(11) -0.03295(10) 0.0662(4) Uani 1 1 d . . . C5 C 0.0284(3) -0.23605(11) 0.02052(10) 0.0733(4) Uani 1 1 d . . . H5A H -0.0698 -0.2351 0.0881 0.088 Uiso 1 1 calc R . . C6 C 0.1186(3) -0.32912(11) -0.02264(11) 0.0777(4) Uani 1 1 d . . . H6A H 0.0844 -0.3904 0.0149 0.093 Uiso 1 1 calc R . . C7 C -0.0242(3) -0.04657(10) 0.01829(11) 0.0724(4) Uani 1 1 d . . . H7A H -0.1348 -0.0522 0.0834 0.087 Uiso 1 1 calc R . . Cl11 Cl -0.3708(7) 0.46091(10) 0.1755(2) 0.1153(9) Uani 0.5448(19) 1 d P . . N1 N -0.3624(15) 0.4158(3) 0.1722(5) 0.0817(11) Uani 0.4552(19) 1 d P . . O1 O -0.3171(12) 0.4976(3) 0.1232(3) 0.1313(15) Uani 0.4552(19) 1 d P . . O2 O -0.4981(7) 0.4128(2) 0.2584(2) 0.1142(8) Uani 0.4552(19) 1 d P . . C11 C -0.2614(3) 0.32955(12) 0.12310(11) 0.0751(4) Uani 1 1 d . . . C12 C -0.3149(3) 0.23910(14) 0.17913(10) 0.0809(4) Uani 1 1 d . . . H12A H -0.4129 0.2406 0.2467 0.097 Uiso 1 1 calc R . . C13 C -0.2227(3) 0.14743(12) 0.13445(11) 0.0771(4) Uani 1 1 d . . . H13A H -0.2570 0.0865 0.1725 0.093 Uiso 1 1 calc R . . C14 C -0.0782(3) 0.14322(11) 0.03295(10) 0.0662(4) Uani 1 1 d . . . C15 C -0.0284(3) 0.23605(11) -0.02052(10) 0.0733(4) Uani 1 1 d . . . H15A H 0.0698 0.2351 -0.0881 0.088 Uiso 1 1 calc R . . C16 C -0.1186(3) 0.32912(11) 0.02264(11) 0.0777(4) Uani 1 1 d . . . H16A H -0.0844 0.3904 -0.0149 0.093 Uiso 1 1 calc R . . C17 C 0.0242(3) 0.04657(10) -0.01829(11) 0.0724(4) Uani 1 1 d . . . H17A H 0.1348 0.0522 -0.0834 0.087 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1148(10) 0.0952(18) 0.1354(16) -0.0467(17) 0.0033(9) 0.0251(13) N11 0.078(2) 0.067(3) 0.099(3) -0.006(3) -0.0024(18) 0.008(2) O11 0.171(3) 0.080(2) 0.146(3) 0.012(2) 0.042(2) 0.0135(19) O12 0.153(2) 0.0942(18) 0.0980(16) -0.0242(15) 0.0336(15) 0.0195(15) C1 0.0596(7) 0.0880(11) 0.0771(9) -0.0144(8) -0.0014(6) 0.0048(7) C2 0.0692(8) 0.1077(13) 0.0665(8) -0.0041(8) 0.0097(6) -0.0008(8) C3 0.0714(8) 0.0847(10) 0.0756(8) 0.0078(7) 0.0072(6) -0.0038(7) C4 0.0525(6) 0.0789(9) 0.0668(8) -0.0032(6) 0.0011(5) -0.0012(6) C5 0.0695(8) 0.0840(10) 0.0669(8) 0.0005(7) 0.0089(6) -0.0002(7) C6 0.0742(8) 0.0792(10) 0.0797(9) 0.0025(7) 0.0038(6) 0.0020(7) C7 0.0619(7) 0.0837(10) 0.0720(8) 0.0042(7) 0.0074(6) -0.0032(7) Cl11 0.1148(10) 0.0952(18) 0.1354(16) -0.0467(17) 0.0033(9) 0.0251(13) N1 0.078(2) 0.067(3) 0.099(3) -0.006(3) -0.0024(18) 0.008(2) O1 0.171(3) 0.080(2) 0.146(3) 0.012(2) 0.042(2) 0.0135(19) O2 0.153(2) 0.0942(18) 0.0980(16) -0.0242(15) 0.0336(15) 0.0195(15) C11 0.0596(7) 0.0880(11) 0.0771(9) -0.0144(8) -0.0014(6) 0.0048(7) C12 0.0692(8) 0.1077(13) 0.0665(8) -0.0041(8) 0.0097(6) -0.0008(8) C13 0.0714(8) 0.0847(10) 0.0756(8) 0.0078(7) 0.0072(6) -0.0038(7) C14 0.0525(6) 0.0789(9) 0.0668(8) -0.0032(6) 0.0011(5) -0.0012(6) C15 0.0695(8) 0.0840(10) 0.0669(8) 0.0005(7) 0.0089(6) -0.0002(7) C16 0.0742(8) 0.0792(10) 0.0797(9) 0.0025(7) 0.0038(6) 0.0020(7) C17 0.0619(7) 0.0837(10) 0.0720(8) 0.0042(7) 0.0074(6) -0.0032(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.587(4) . ? Cl1 O11 0.834(3) . ? Cl1 O12 1.311(4) . ? Cl1 C1 1.875(2) . ? N11 O12 1.206(7) . ? N11 O11 1.236(8) . ? N11 C1 1.338(4) . ? C1 C6 1.377(2) . ? C1 C2 1.379(2) . ? C2 C3 1.364(2) . ? C2 H2A 0.9300 . ? C3 C4 1.3930(18) . ? C3 H3A 0.9300 . ? C4 C5 1.3871(18) . ? C4 C7 1.4651(19) . ? C5 C6 1.3695(18) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.304(2) . ? C7 H7A 0.9300 . ? Cl11 N1 0.587(4) . ? Cl11 O1 0.834(3) . ? Cl11 O2 1.311(4) . ? Cl11 C11 1.875(2) . ? N1 O2 1.206(7) . ? N1 O1 1.236(8) . ? N1 C11 1.338(4) . ? C11 C16 1.377(2) . ? C11 C12 1.379(2) . ? C12 C13 1.364(2) . ? C12 H12A 0.9300 . ? C13 C14 1.3930(18) . ? C13 H13A 0.9300 . ? C14 C15 1.3871(18) . ? C14 C17 1.4651(19) . ? C15 C16 1.3695(18) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 119.9(12) . . ? N11 Cl1 O12 66.7(8) . . ? O11 Cl1 O12 170.8(5) . . ? N11 Cl1 C1 19.7(8) . . ? O11 Cl1 C1 100.5(4) . . ? O12 Cl1 C1 86.38(15) . . ? Cl1 N11 O12 86.7(8) . . ? Cl1 N11 O11 35.8(8) . . ? O12 N11 O11 122.2(4) . . ? Cl1 N11 C1 151.7(11) . . ? O12 N11 C1 121.4(5) . . ? O11 N11 C1 116.3(5) . . ? Cl1 O11 N11 24.3(4) . . ? N11 O12 Cl1 26.55(19) . . ? N11 C1 C6 123.3(3) . . ? N11 C1 C2 115.4(3) . . ? C6 C1 C2 121.33(14) . . ? N11 C1 Cl1 8.5(4) . . ? C6 C1 Cl1 114.84(16) . . ? C2 C1 Cl1 123.82(15) . . ? C3 C2 C1 119.30(13) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 121.37(15) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.42(13) . . ? C5 C4 C7 119.31(12) . . ? C3 C4 C7 123.27(13) . . ? C6 C5 C4 122.33(13) . . ? C6 C5 H5A 118.8 . . ? C4 C5 H5A 118.8 . . ? C5 C6 C1 118.24(14) . . ? C5 C6 H6A 120.9 . . ? C1 C6 H6A 120.9 . . ? C17 C7 C4 126.51(16) . . ? C17 C7 H7A 116.7 . . ? C4 C7 H7A 116.7 . . ? N1 Cl11 O1 119.9(12) . . ? N1 Cl11 O2 66.7(8) . . ? O1 Cl11 O2 170.8(5) . . ? N1 Cl11 C11 19.7(8) . . ? O1 Cl11 C11 100.5(4) . . ? O2 Cl11 C11 86.38(15) . . ? Cl11 N1 O2 86.7(8) . . ? Cl11 N1 O1 35.8(8) . . ? O2 N1 O1 122.2(4) . . ? Cl11 N1 C11 151.7(11) . . ? O2 N1 C11 121.4(5) . . ? O1 N1 C11 116.3(5) . . ? Cl11 O1 N1 24.3(4) . . ? N1 O2 Cl11 26.55(19) . . ? N1 C11 C16 123.3(3) . . ? N1 C11 C12 115.4(3) . . ? C16 C11 C12 121.33(14) . . ? N1 C11 Cl11 8.5(4) . . ? C16 C11 Cl11 114.84(16) . . ? C12 C11 Cl11 123.82(15) . . ? C13 C12 C11 119.30(13) . . ? C13 C12 H12A 120.3 . . ? C11 C12 H12A 120.3 . . ? C12 C13 C14 121.37(15) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 117.42(13) . . ? C15 C14 C17 119.31(12) . . ? C13 C14 C17 123.27(13) . . ? C16 C15 C14 122.33(13) . . ? C16 C15 H15A 118.8 . . ? C14 C15 H15A 118.8 . . ? C15 C16 C11 118.24(14) . . ? C15 C16 H16A 120.9 . . ? C11 C16 H16A 120.9 . . ? C7 C17 C14 126.51(16) . . ? C7 C17 H17A 116.7 . . ? C14 C17 H17A 116.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.9(6) . . . . ? C1 Cl1 N11 O12 -175(2) . . . . ? O12 Cl1 N11 O11 -172.9(6) . . . . ? C1 Cl1 N11 O11 13(3) . . . . ? O11 Cl1 N11 C1 -13(3) . . . . ? O12 Cl1 N11 C1 175(2) . . . . ? O12 Cl1 O11 N11 134(4) . . . . ? C1 Cl1 O11 N11 -4.3(9) . . . . ? O12 N11 O11 Cl1 -8.4(7) . . . . ? C1 N11 O11 Cl1 173.4(14) . . . . ? O11 N11 O12 Cl1 4.9(4) . . . . ? C1 N11 O12 Cl1 -177.0(12) . . . . ? O11 Cl1 O12 N11 -137(3) . . . . ? C1 Cl1 O12 N11 1.8(8) . . . . ? Cl1 N11 C1 C6 9(2) . . . . ? O12 N11 C1 C6 -177.2(4) . . . . ? O11 N11 C1 C6 1.0(7) . . . . ? Cl1 N11 C1 C2 -172(2) . . . . ? O12 N11 C1 C2 1.7(6) . . . . ? O11 N11 C1 C2 179.9(4) . . . . ? O12 N11 C1 Cl1 174(3) . . . . ? O11 N11 C1 Cl1 -8.2(18) . . . . ? O11 Cl1 C1 N11 169(2) . . . . ? O12 Cl1 C1 N11 -5(2) . . . . ? N11 Cl1 C1 C6 -172(2) . . . . ? O11 Cl1 C1 C6 -2.7(5) . . . . ? O12 Cl1 C1 C6 -176.59(16) . . . . ? N11 Cl1 C1 C2 9(2) . . . . ? O11 Cl1 C1 C2 177.7(4) . . . . ? O12 Cl1 C1 C2 3.8(2) . . . . ? N11 C1 C2 C3 -179.3(3) . . . . ? C6 C1 C2 C3 -0.4(2) . . . . ? Cl1 C1 C2 C3 179.23(14) . . . . ? C1 C2 C3 C4 0.5(2) . . . . ? C2 C3 C4 C5 -0.64(19) . . . . ? C2 C3 C4 C7 179.90(11) . . . . ? C3 C4 C5 C6 0.61(18) . . . . ? C7 C4 C5 C6 -179.90(11) . . . . ? C4 C5 C6 C1 -0.47(19) . . . . ? N11 C1 C6 C5 179.2(3) . . . . ? C2 C1 C6 C5 0.3(2) . . . . ? Cl1 C1 C6 C5 -179.30(13) . . . . ? C5 C4 C7 C17 175.64(16) . . . . ? C3 C4 C7 C17 -4.9(2) . . . . ? O1 Cl11 N1 O2 -172.9(6) . . . . ? C11 Cl11 N1 O2 175(2) . . . . ? O2 Cl11 N1 O1 172.9(6) . . . . ? C11 Cl11 N1 O1 -13(3) . . . . ? O1 Cl11 N1 C11 13(3) . . . . ? O2 Cl11 N1 C11 -175(2) . . . . ? O2 Cl11 O1 N1 -134(4) . . . . ? C11 Cl11 O1 N1 4.3(9) . . . . ? O2 N1 O1 Cl11 8.4(7) . . . . ? C11 N1 O1 Cl11 -173.4(14) . . . . ? O1 N1 O2 Cl11 -4.9(4) . . . . ? C11 N1 O2 Cl11 177.0(12) . . . . ? O1 Cl11 O2 N1 137(3) . . . . ? C11 Cl11 O2 N1 -1.8(8) . . . . ? Cl11 N1 C11 C16 -9(2) . . . . ? O2 N1 C11 C16 177.2(4) . . . . ? O1 N1 C11 C16 -1.0(7) . . . . ? Cl11 N1 C11 C12 172(2) . . . . ? O2 N1 C11 C12 -1.7(6) . . . . ? O1 N1 C11 C12 -179.9(4) . . . . ? O2 N1 C11 Cl11 -174(3) . . . . ? O1 N1 C11 Cl11 8.2(18) . . . . ? O1 Cl11 C11 N1 -169(2) . . . . ? O2 Cl11 C11 N1 5(2) . . . . ? N1 Cl11 C11 C16 172(2) . . . . ? O1 Cl11 C11 C16 2.7(5) . . . . ? O2 Cl11 C11 C16 176.59(16) . . . . ? N1 Cl11 C11 C12 -9(2) . . . . ? O1 Cl11 C11 C12 -177.7(4) . . . . ? O2 Cl11 C11 C12 -3.8(2) . . . . ? N1 C11 C12 C13 179.3(3) . . . . ? C16 C11 C12 C13 0.4(2) . . . . ? Cl11 C11 C12 C13 -179.23(14) . . . . ? C11 C12 C13 C14 -0.5(2) . . . . ? C12 C13 C14 C15 0.64(19) . . . . ? C12 C13 C14 C17 -179.90(11) . . . . ? C13 C14 C15 C16 -0.61(18) . . . . ? C17 C14 C15 C16 179.90(11) . . . . ? C14 C15 C16 C11 0.47(19) . . . . ? N1 C11 C16 C15 -179.2(3) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? Cl11 C11 C16 C15 179.30(13) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.64(16) . . . . ? C13 C14 C17 C7 4.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 27.76 _diffrn_measured_fraction_theta_full 0.920 _refine_diff_density_max 0.092 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.034 # start Validation Reply Form _vrf_SYMMG02_CNS-Me2CO-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-Me2CO-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.92 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:18. ; # end Validation Reply Form #===END data_CNS-EtOAc-small-P21_c _database_code_depnum_ccdc_archive 'CCDC 761222' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9227(2) _cell_length_b 12.9764(7) _cell_length_c 12.2535(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.200(2) _cell_angle_gamma 90.00 _cell_volume 622.76(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3440 _cell_measurement_theta_min 3.1395 _cell_measurement_theta_max 22.987 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.102711 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3420 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.80 _reflns_number_total 2164 _reflns_number_gt 1111 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1102P)^2^+0.1649P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 2164 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1370 _refine_ls_R_factor_gt 0.0802 _refine_ls_wR_factor_ref 0.2719 _refine_ls_wR_factor_gt 0.2413 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3701(18) -0.4608(2) -0.1745(7) 0.122(2) Uani 0.50 1 d P . . N11 N 0.363(4) -0.4190(8) -0.1739(14) 0.084(3) Uani 0.50 1 d P . . O11 O 0.309(3) -0.4982(8) -0.1223(7) 0.138(3) Uani 0.50 1 d P . . O12 O 0.5016(14) -0.4150(4) -0.2585(5) 0.1176(18) Uani 0.50 1 d P . . C1 C 0.2606(7) -0.3288(2) -0.1229(3) 0.0743(8) Uani 1 1 d . . . C2 C 0.3167(7) -0.2384(3) -0.1791(2) 0.0861(9) Uani 1 1 d . . . H2A H 0.4170 -0.2395 -0.2461 0.103 Uiso 1 1 calc R . . C3 C 0.2216(7) -0.1480(2) -0.1338(2) 0.0784(9) Uani 1 1 d . . . H3A H 0.2530 -0.0870 -0.1718 0.094 Uiso 1 1 calc R . . C4 C 0.0797(6) -0.1437(2) -0.0333(2) 0.0700(8) Uani 1 1 d . . . C5 C 0.0281(7) -0.2356(2) 0.0207(2) 0.0762(8) Uani 1 1 d . . . H5A H -0.0703 -0.2346 0.0880 0.091 Uiso 1 1 calc R . . C6 C 0.1204(7) -0.3290(2) -0.0236(3) 0.0810(9) Uani 1 1 d . . . H6A H 0.0874 -0.3904 0.0135 0.097 Uiso 1 1 calc R . . C7 C -0.0245(7) -0.0470(2) 0.0189(2) 0.0751(8) Uani 1 1 d . . . H7A H -0.1340 -0.0527 0.0840 0.090 Uiso 1 1 calc R . . Cl11 Cl -0.3701(18) 0.4608(2) 0.1745(7) 0.122(2) Uani 0.50 1 d P . . N1 N -0.363(4) 0.4190(8) 0.1739(14) 0.084(3) Uani 0.50 1 d P . . O1 O -0.309(3) 0.4982(8) 0.1223(7) 0.138(3) Uani 0.50 1 d P . . O2 O -0.5016(14) 0.4150(4) 0.2585(5) 0.1176(18) Uani 0.50 1 d P . . C11 C -0.2606(7) 0.3288(2) 0.1229(3) 0.0743(8) Uani 1 1 d . . . C12 C -0.3167(7) 0.2384(3) 0.1791(2) 0.0861(9) Uani 1 1 d . . . H12A H -0.4170 0.2395 0.2461 0.103 Uiso 1 1 calc R . . C13 C -0.2216(7) 0.1480(2) 0.1338(2) 0.0784(9) Uani 1 1 d . . . H13A H -0.2530 0.0870 0.1718 0.094 Uiso 1 1 calc R . . C14 C -0.0797(6) 0.1437(2) 0.0333(2) 0.0700(8) Uani 1 1 d . . . C15 C -0.0281(7) 0.2356(2) -0.0207(2) 0.0762(8) Uani 1 1 d . . . H15A H 0.0703 0.2346 -0.0880 0.091 Uiso 1 1 calc R . . C16 C -0.1204(7) 0.3290(2) 0.0236(3) 0.0810(9) Uani 1 1 d . . . H16A H -0.0874 0.3904 -0.0135 0.097 Uiso 1 1 calc R . . C17 C 0.0245(7) 0.0470(2) -0.0189(2) 0.0751(8) Uani 1 1 d . . . H17A H 0.1340 0.0527 -0.0840 0.090 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.131(2) 0.090(4) 0.144(4) -0.049(4) 0.003(3) 0.024(3) N11 0.091(5) 0.062(7) 0.097(8) 0.001(6) -0.008(5) 0.006(6) O11 0.194(7) 0.082(5) 0.141(7) 0.010(4) 0.040(5) 0.014(4) O12 0.163(5) 0.077(4) 0.114(4) -0.032(3) 0.020(3) 0.017(3) C1 0.0723(17) 0.0675(19) 0.0825(19) -0.0122(15) -0.0033(14) 0.0033(13) C2 0.0808(19) 0.108(3) 0.0695(19) -0.0044(17) 0.0065(15) 0.0012(16) C3 0.0814(18) 0.073(2) 0.0812(19) 0.0057(15) 0.0065(14) -0.0016(14) C4 0.0638(15) 0.0744(19) 0.0711(17) -0.0058(14) -0.0021(12) 0.0009(12) C5 0.0843(18) 0.075(2) 0.0694(17) 0.0046(15) 0.0063(13) -0.0039(14) C6 0.0885(19) 0.0641(19) 0.090(2) -0.0021(15) -0.0016(16) 0.0055(14) C7 0.0758(17) 0.0710(19) 0.0786(18) 0.0046(14) 0.0037(13) -0.0037(14) Cl11 0.131(2) 0.090(4) 0.144(4) -0.049(4) 0.003(3) 0.024(3) N1 0.091(5) 0.062(7) 0.097(8) 0.001(6) -0.008(5) 0.006(6) O1 0.194(7) 0.082(5) 0.141(7) 0.010(4) 0.040(5) 0.014(4) O2 0.163(5) 0.077(4) 0.114(4) -0.032(3) 0.020(3) 0.017(3) C11 0.0723(17) 0.0675(19) 0.0825(19) -0.0122(15) -0.0033(14) 0.0033(13) C12 0.0808(19) 0.108(3) 0.0695(19) -0.0044(17) 0.0065(15) 0.0012(16) C13 0.0814(18) 0.073(2) 0.0812(19) 0.0057(15) 0.0065(14) -0.0016(14) C14 0.0638(15) 0.0744(19) 0.0711(17) -0.0058(14) -0.0021(12) 0.0009(12) C15 0.0843(18) 0.075(2) 0.0694(17) 0.0046(15) 0.0063(13) -0.0039(14) C16 0.0885(19) 0.0641(19) 0.090(2) -0.0021(15) -0.0016(16) 0.0055(14) C17 0.0758(17) 0.0710(19) 0.0786(18) 0.0046(14) 0.0037(13) -0.0037(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.544(11) . ? Cl1 O11 0.847(8) . ? Cl1 O12 1.318(9) . ? Cl1 C1 1.884(4) . ? N11 O12 1.198(19) . ? N11 O11 1.23(2) . ? N11 C1 1.396(10) . ? C1 C6 1.363(4) . ? C1 C2 1.385(4) . ? C2 C3 1.359(4) . ? C2 H2A 0.9300 . ? C3 C4 1.381(4) . ? C3 H3A 0.9300 . ? C4 C5 1.384(4) . ? C4 C7 1.476(4) . ? C5 C6 1.384(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.324(5) . ? C7 H7A 0.9300 . ? Cl11 N1 0.544(11) . ? Cl11 O1 0.847(8) . ? Cl11 O2 1.318(9) . ? Cl11 C11 1.884(4) . ? N1 O2 1.198(19) . ? N1 O1 1.23(2) . ? N1 C11 1.396(10) . ? C11 C16 1.363(4) . ? C11 C12 1.385(4) . ? C12 C13 1.359(4) . ? C12 H12A 0.9300 . ? C13 C14 1.381(4) . ? C13 H13A 0.9300 . ? C14 C15 1.384(4) . ? C14 C17 1.476(4) . ? C15 C16 1.384(4) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 123(3) . . ? N11 Cl1 O12 65(3) . . ? O11 Cl1 O12 170.5(10) . . ? N11 Cl1 C1 22(2) . . ? O11 Cl1 C1 100.8(10) . . ? O12 Cl1 C1 87.6(3) . . ? Cl1 N11 O12 90(2) . . ? Cl1 N11 O11 35(2) . . ? O12 N11 O11 125.4(10) . . ? Cl1 N11 C1 149(3) . . ? O12 N11 C1 120.5(11) . . ? O11 N11 C1 114.1(12) . . ? Cl1 O11 N11 21.7(10) . . ? N11 O12 Cl1 24.4(5) . . ? C6 C1 C2 121.9(3) . . ? C6 C1 N11 122.6(8) . . ? C2 C1 N11 115.5(8) . . ? C6 C1 Cl1 114.1(4) . . ? C2 C1 Cl1 124.0(3) . . ? N11 C1 Cl1 8.5(9) . . ? C3 C2 C1 118.3(3) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C2 C3 C4 122.2(3) . . ? C2 C3 H3A 118.9 . . ? C4 C3 H3A 118.9 . . ? C3 C4 C5 117.9(3) . . ? C3 C4 C7 123.8(3) . . ? C5 C4 C7 118.3(3) . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C1 C6 C5 118.4(3) . . ? C1 C6 H6A 120.8 . . ? C5 C6 H6A 120.8 . . ? C17 C7 C4 125.6(4) . . ? C17 C7 H7A 117.2 . . ? C4 C7 H7A 117.2 . . ? N1 Cl11 O1 123(3) . . ? N1 Cl11 O2 65(3) . . ? O1 Cl11 O2 170.5(10) . . ? N1 Cl11 C11 22(2) . . ? O1 Cl11 C11 100.8(10) . . ? O2 Cl11 C11 87.6(3) . . ? Cl11 N1 O2 90(2) . . ? Cl11 N1 O1 35(2) . . ? O2 N1 O1 125.4(10) . . ? Cl11 N1 C11 149(3) . . ? O2 N1 C11 120.5(11) . . ? O1 N1 C11 114.1(12) . . ? Cl11 O1 N1 21.7(10) . . ? N1 O2 Cl11 24.4(5) . . ? C16 C11 C12 121.9(3) . . ? C16 C11 N1 122.6(8) . . ? C12 C11 N1 115.5(8) . . ? C16 C11 Cl11 114.1(4) . . ? C12 C11 Cl11 124.0(3) . . ? N1 C11 Cl11 8.5(9) . . ? C13 C12 C11 118.3(3) . . ? C13 C12 H12A 120.8 . . ? C11 C12 H12A 120.8 . . ? C12 C13 C14 122.2(3) . . ? C12 C13 H13A 118.9 . . ? C14 C13 H13A 118.9 . . ? C13 C14 C15 117.9(3) . . ? C13 C14 C17 123.8(3) . . ? C15 C14 C17 118.3(3) . . ? C14 C15 C16 121.2(3) . . ? C14 C15 H15A 119.4 . . ? C16 C15 H15A 119.4 . . ? C11 C16 C15 118.4(3) . . ? C11 C16 H16A 120.8 . . ? C15 C16 H16A 120.8 . . ? C7 C17 C14 125.6(4) . . ? C7 C17 H17A 117.2 . . ? C14 C17 H17A 117.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 174.6(16) . . . . ? C1 Cl1 N11 O12 -179(6) . . . . ? O12 Cl1 N11 O11 -174.6(16) . . . . ? C1 Cl1 N11 O11 7(7) . . . . ? O11 Cl1 N11 C1 -7(7) . . . . ? O12 Cl1 N11 C1 179(6) . . . . ? O12 Cl1 O11 N11 149(9) . . . . ? C1 Cl1 O11 N11 -3(3) . . . . ? O12 N11 O11 Cl1 -6.6(19) . . . . ? C1 N11 O11 Cl1 176(4) . . . . ? O11 N11 O12 Cl1 3.8(11) . . . . ? C1 N11 O12 Cl1 -179(3) . . . . ? O11 Cl1 O12 N11 -152(8) . . . . ? C1 Cl1 O12 N11 1(2) . . . . ? Cl1 N11 C1 C6 6(6) . . . . ? O12 N11 C1 C6 -176.0(9) . . . . ? O11 N11 C1 C6 1.3(17) . . . . ? Cl1 N11 C1 C2 -176(5) . . . . ? O12 N11 C1 C2 2.8(15) . . . . ? O11 N11 C1 C2 -179.9(11) . . . . ? O12 N11 C1 Cl1 178(7) . . . . ? O11 N11 C1 Cl1 -4(4) . . . . ? N11 Cl1 C1 C6 -175(5) . . . . ? O11 Cl1 C1 C6 -0.6(10) . . . . ? O12 Cl1 C1 C6 -176.1(4) . . . . ? N11 Cl1 C1 C2 5(6) . . . . ? O11 Cl1 C1 C2 179.0(9) . . . . ? O12 Cl1 C1 C2 3.6(6) . . . . ? O11 Cl1 C1 N11 174(6) . . . . ? O12 Cl1 C1 N11 -1(5) . . . . ? C6 C1 C2 C3 -1.3(4) . . . . ? N11 C1 C2 C3 179.8(7) . . . . ? Cl1 C1 C2 C3 179.0(3) . . . . ? C1 C2 C3 C4 1.6(4) . . . . ? C2 C3 C4 C5 -1.4(4) . . . . ? C2 C3 C4 C7 179.5(2) . . . . ? C3 C4 C5 C6 1.0(4) . . . . ? C7 C4 C5 C6 -179.9(2) . . . . ? C2 C1 C6 C5 0.9(4) . . . . ? N11 C1 C6 C5 179.7(7) . . . . ? Cl1 C1 C6 C5 -179.4(3) . . . . ? C4 C5 C6 C1 -0.8(4) . . . . ? C3 C4 C7 C17 -4.9(5) . . . . ? C5 C4 C7 C17 176.0(3) . . . . ? O1 Cl11 N1 O2 -174.6(16) . . . . ? C11 Cl11 N1 O2 179(6) . . . . ? O2 Cl11 N1 O1 174.6(16) . . . . ? C11 Cl11 N1 O1 -7(7) . . . . ? O1 Cl11 N1 C11 7(7) . . . . ? O2 Cl11 N1 C11 -179(6) . . . . ? O2 Cl11 O1 N1 -149(9) . . . . ? C11 Cl11 O1 N1 3(3) . . . . ? O2 N1 O1 Cl11 6.6(19) . . . . ? C11 N1 O1 Cl11 -176(4) . . . . ? O1 N1 O2 Cl11 -3.8(11) . . . . ? C11 N1 O2 Cl11 179(3) . . . . ? O1 Cl11 O2 N1 152(8) . . . . ? C11 Cl11 O2 N1 -1(2) . . . . ? Cl11 N1 C11 C16 -6(6) . . . . ? O2 N1 C11 C16 176.0(9) . . . . ? O1 N1 C11 C16 -1.3(17) . . . . ? Cl11 N1 C11 C12 176(5) . . . . ? O2 N1 C11 C12 -2.8(15) . . . . ? O1 N1 C11 C12 179.9(11) . . . . ? O2 N1 C11 Cl11 -178(7) . . . . ? O1 N1 C11 Cl11 4(4) . . . . ? N1 Cl11 C11 C16 175(5) . . . . ? O1 Cl11 C11 C16 0.6(10) . . . . ? O2 Cl11 C11 C16 176.1(4) . . . . ? N1 Cl11 C11 C12 -5(6) . . . . ? O1 Cl11 C11 C12 -179.0(9) . . . . ? O2 Cl11 C11 C12 -3.6(6) . . . . ? O1 Cl11 C11 N1 -174(6) . . . . ? O2 Cl11 C11 N1 1(5) . . . . ? C16 C11 C12 C13 1.3(4) . . . . ? N1 C11 C12 C13 -179.8(7) . . . . ? Cl11 C11 C12 C13 -179.0(3) . . . . ? C11 C12 C13 C14 -1.6(4) . . . . ? C12 C13 C14 C15 1.4(4) . . . . ? C12 C13 C14 C17 -179.5(2) . . . . ? C13 C14 C15 C16 -1.0(4) . . . . ? C17 C14 C15 C16 179.9(2) . . . . ? C12 C11 C16 C15 -0.9(4) . . . . ? N1 C11 C16 C15 -179.7(7) . . . . ? Cl11 C11 C16 C15 179.4(3) . . . . ? C14 C15 C16 C11 0.8(4) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 4.9(5) . . . . ? C15 C14 C17 C7 -176.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.867 _diffrn_reflns_theta_full 27.80 _diffrn_measured_fraction_theta_full 0.867 _refine_diff_density_max 0.225 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.057 # start Validation Reply Form _vrf_ABSTM02_CNS-EtOAc-small-P21_c ; PROBLEM: The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:22. ; _vrf_SYMMG02_CNS-EtOAc-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-EtOAc-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.87 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:22. ; _vrf_PLAT061_CNS-EtOAc-small-P21_c ; PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.11 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:22. ; # end Validation Reply Form #===END data_CNS-EtOAc-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761223' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9227(2) _cell_length_b 12.9764(7) _cell_length_c 12.2535(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.200(2) _cell_angle_gamma 90.00 _cell_volume 622.76(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3440 _cell_measurement_theta_min 3.1395 _cell_measurement_theta_max 22.987 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.102711 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3420 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.80 _reflns_number_total 2164 _reflns_number_gt 1111 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1102P)^2^+0.1649P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(2) _refine_ls_number_reflns 2164 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1239 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.2176 _refine_ls_wR_factor_gt 0.1727 _refine_ls_goodness_of_fit_ref 0.890 _refine_ls_restrained_S_all 0.890 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3669(10) -0.46023(19) -0.1752(3) 0.1191(15) Uani 0.377(3) 1 d P . . N11 N 0.372(2) -0.4172(6) -0.1736(8) 0.088(2) Uani 0.623(3) 1 d P . . O11 O 0.3097(19) -0.4986(4) -0.1241(5) 0.129(2) Uani 0.623(3) 1 d P . . O12 O 0.5018(12) -0.4134(3) -0.2588(4) 0.1145(14) Uani 0.623(3) 1 d P . . C1 C 0.2615(5) -0.32926(19) -0.1230(2) 0.0751(7) Uani 1 1 d . . . C2 C 0.3166(6) -0.2388(2) -0.17954(19) 0.0823(8) Uani 1 1 d . . . H2A H 0.4157 -0.2400 -0.2467 0.099 Uiso 1 1 calc R . . C3 C 0.2214(6) -0.1476(2) -0.1340(2) 0.0793(7) Uani 1 1 d . . . H3A H 0.2534 -0.0866 -0.1720 0.095 Uiso 1 1 calc R . . C4 C 0.0796(5) -0.14300(18) -0.03356(18) 0.0683(6) Uani 1 1 d . . . C5 C 0.0285(6) -0.23603(19) 0.02052(19) 0.0759(7) Uani 1 1 d . . . H5A H -0.0704 -0.2352 0.0878 0.091 Uiso 1 1 calc R . . C6 C 0.1213(6) -0.32916(19) -0.0235(2) 0.0802(7) Uani 1 1 d . . . H6A H 0.0890 -0.3905 0.0138 0.096 Uiso 1 1 calc R . . C7 C -0.0246(6) -0.04665(17) 0.0189(2) 0.0744(7) Uani 1 1 d . . . H7A H -0.1341 -0.0524 0.0840 0.089 Uiso 1 1 calc R . . Cl11 Cl -0.3669(10) 0.46023(19) 0.1752(3) 0.1191(15) Uani 0.623(3) 1 d P . . N1 N -0.372(2) 0.4172(6) 0.1736(8) 0.088(2) Uani 0.377(3) 1 d P . . O1 O -0.3097(19) 0.4986(4) 0.1241(5) 0.129(2) Uani 0.377(3) 1 d P . . O2 O -0.5018(12) 0.4134(3) 0.2588(4) 0.1145(14) Uani 0.377(3) 1 d P . . C11 C -0.2615(5) 0.32926(19) 0.1230(2) 0.0751(7) Uani 1 1 d . . . C12 C -0.3166(6) 0.2388(2) 0.17954(19) 0.0823(8) Uani 1 1 d . . . H12A H -0.4157 0.2400 0.2467 0.099 Uiso 1 1 calc R . . C13 C -0.2214(6) 0.1476(2) 0.1340(2) 0.0793(7) Uani 1 1 d . . . H13A H -0.2534 0.0866 0.1720 0.095 Uiso 1 1 calc R . . C14 C -0.0796(5) 0.14300(18) 0.03356(18) 0.0683(6) Uani 1 1 d . . . C15 C -0.0285(6) 0.23603(19) -0.02052(19) 0.0759(7) Uani 1 1 d . . . H15A H 0.0704 0.2352 -0.0878 0.091 Uiso 1 1 calc R . . C16 C -0.1213(6) 0.32916(19) 0.0235(2) 0.0802(7) Uani 1 1 d . . . H16A H -0.0890 0.3905 -0.0138 0.096 Uiso 1 1 calc R . . C17 C 0.0246(6) 0.04665(17) -0.0189(2) 0.0744(7) Uani 1 1 d . . . H17A H 0.1341 0.0524 -0.0840 0.089 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1278(19) 0.084(2) 0.145(3) -0.046(2) 0.0024(18) 0.018(2) N11 0.093(4) 0.062(5) 0.105(5) -0.007(4) -0.017(3) -0.003(4) O11 0.185(5) 0.058(3) 0.146(5) 0.011(3) 0.036(4) 0.016(3) O12 0.163(4) 0.079(3) 0.103(3) -0.027(2) 0.029(3) 0.017(2) C1 0.0683(14) 0.0737(17) 0.0823(16) -0.0142(13) -0.0037(11) 0.0049(11) C2 0.0817(16) 0.096(2) 0.0694(16) -0.0035(13) 0.0089(12) 0.0003(13) C3 0.0796(15) 0.0730(17) 0.0851(17) 0.0095(13) 0.0025(12) -0.0041(11) C4 0.0640(12) 0.0708(15) 0.0694(14) -0.0048(12) -0.0020(10) 0.0012(10) C5 0.0834(15) 0.0747(17) 0.0698(14) 0.0042(12) 0.0066(11) -0.0020(12) C6 0.0866(16) 0.0668(17) 0.0867(18) -0.0001(13) 0.0008(13) 0.0031(12) C7 0.0743(13) 0.0734(16) 0.0755(15) 0.0045(12) 0.0032(11) -0.0033(12) Cl11 0.1278(19) 0.084(2) 0.145(3) -0.046(2) 0.0024(18) 0.018(2) N1 0.093(4) 0.062(5) 0.105(5) -0.007(4) -0.017(3) -0.003(4) O1 0.185(5) 0.058(3) 0.146(5) 0.011(3) 0.036(4) 0.016(3) O2 0.163(4) 0.079(3) 0.103(3) -0.027(2) 0.029(3) 0.017(2) C11 0.0683(14) 0.0737(17) 0.0823(16) -0.0142(13) -0.0037(11) 0.0049(11) C12 0.0817(16) 0.096(2) 0.0694(16) -0.0035(13) 0.0089(12) 0.0003(13) C13 0.0796(15) 0.0730(17) 0.0851(17) 0.0095(13) 0.0025(12) -0.0041(11) C14 0.0640(12) 0.0708(15) 0.0694(14) -0.0048(12) -0.0020(10) 0.0012(10) C15 0.0834(15) 0.0747(17) 0.0698(14) 0.0042(12) 0.0066(11) -0.0020(12) C16 0.0866(16) 0.0668(17) 0.0867(18) -0.0001(13) 0.0008(13) 0.0031(12) C17 0.0743(13) 0.0734(16) 0.0755(15) 0.0045(12) 0.0032(11) -0.0033(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.559(7) . ? Cl1 O11 0.840(5) . ? Cl1 O12 1.327(6) . ? Cl1 C1 1.870(3) . ? N11 O12 1.188(10) . ? N11 O11 1.248(11) . ? N11 C1 1.380(8) . ? C1 C6 1.365(3) . ? C1 C2 1.386(4) . ? C2 C3 1.370(4) . ? C2 H2A 0.9300 . ? C3 C4 1.380(3) . ? C3 H3A 0.9300 . ? C4 C5 1.397(3) . ? C4 C7 1.474(3) . ? C5 C6 1.381(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.314(4) . ? C7 H7A 0.9300 . ? Cl11 N1 0.559(7) . ? Cl11 O1 0.840(5) . ? Cl11 O2 1.327(6) . ? Cl11 C11 1.870(3) . ? N1 O2 1.188(10) . ? N1 O1 1.248(11) . ? N1 C11 1.380(8) . ? C11 C16 1.365(3) . ? C11 C12 1.386(4) . ? C12 C13 1.370(4) . ? C12 H12A 0.9300 . ? C13 C14 1.380(3) . ? C13 H13A 0.9300 . ? C14 C15 1.397(3) . ? C14 C17 1.474(3) . ? C15 C16 1.381(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 125.2(16) . . ? N11 Cl1 O12 63.5(13) . . ? O11 Cl1 O12 169.1(6) . . ? N11 Cl1 C1 24.3(12) . . ? O11 Cl1 C1 102.1(6) . . ? O12 Cl1 C1 87.3(3) . . ? Cl1 N11 O12 91.6(13) . . ? Cl1 N11 O11 33.3(11) . . ? O12 N11 O11 124.6(7) . . ? Cl1 N11 C1 146.1(17) . . ? O12 N11 C1 121.4(7) . . ? O11 N11 C1 114.0(8) . . ? Cl1 O11 N11 21.4(5) . . ? N11 O12 Cl1 24.9(4) . . ? C6 C1 C2 121.8(2) . . ? C6 C1 N11 123.6(5) . . ? C2 C1 N11 114.5(5) . . ? C6 C1 Cl1 114.4(2) . . ? C2 C1 Cl1 123.7(2) . . ? N11 C1 Cl1 9.6(5) . . ? C3 C2 C1 118.3(2) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C2 C3 C4 122.2(3) . . ? C2 C3 H3A 118.9 . . ? C4 C3 H3A 118.9 . . ? C3 C4 C5 117.5(2) . . ? C3 C4 C7 124.1(2) . . ? C5 C4 C7 118.4(2) . . ? C4 C5 C6 121.5(2) . . ? C4 C5 H5A 119.2 . . ? C6 C5 H5A 119.2 . . ? C1 C6 C5 118.6(2) . . ? C1 C6 H6A 120.7 . . ? C5 C6 H6A 120.7 . . ? C17 C7 C4 125.3(3) . . ? C17 C7 H7A 117.3 . . ? C4 C7 H7A 117.3 . . ? N1 Cl11 O1 125.2(16) . . ? N1 Cl11 O2 63.5(13) . . ? O1 Cl11 O2 169.1(6) . . ? N1 Cl11 C11 24.3(12) . . ? O1 Cl11 C11 102.1(6) . . ? O2 Cl11 C11 87.3(3) . . ? Cl11 N1 O2 91.6(13) . . ? Cl11 N1 O1 33.3(11) . . ? O2 N1 O1 124.6(7) . . ? Cl11 N1 C11 146.1(17) . . ? O2 N1 C11 121.4(7) . . ? O1 N1 C11 114.0(8) . . ? Cl11 O1 N1 21.4(5) . . ? N1 O2 Cl11 24.9(4) . . ? C16 C11 C12 121.8(2) . . ? C16 C11 N1 123.6(5) . . ? C12 C11 N1 114.5(5) . . ? C16 C11 Cl11 114.4(2) . . ? C12 C11 Cl11 123.7(2) . . ? N1 C11 Cl11 9.6(5) . . ? C13 C12 C11 118.3(2) . . ? C13 C12 H12A 120.8 . . ? C11 C12 H12A 120.8 . . ? C12 C13 C14 122.2(3) . . ? C12 C13 H13A 118.9 . . ? C14 C13 H13A 118.9 . . ? C13 C14 C15 117.5(2) . . ? C13 C14 C17 124.1(2) . . ? C15 C14 C17 118.4(2) . . ? C14 C15 C16 121.5(2) . . ? C14 C15 H15A 119.2 . . ? C16 C15 H15A 119.2 . . ? C11 C16 C15 118.6(2) . . ? C11 C16 H16A 120.7 . . ? C15 C16 H16A 120.7 . . ? C7 C17 C14 125.3(3) . . ? C7 C17 H17A 117.3 . . ? C14 C17 H17A 117.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.3(10) . . . . ? C1 Cl1 N11 O12 -167(3) . . . . ? O12 Cl1 N11 O11 -172.3(10) . . . . ? C1 Cl1 N11 O11 20(4) . . . . ? O11 Cl1 N11 C1 -20(4) . . . . ? O12 Cl1 N11 C1 167(3) . . . . ? O12 Cl1 O11 N11 141(5) . . . . ? C1 Cl1 O11 N11 -8.4(16) . . . . ? O12 N11 O11 Cl1 -9.4(12) . . . . ? C1 N11 O11 Cl1 168(2) . . . . ? O11 N11 O12 Cl1 5.2(7) . . . . ? C1 N11 O12 Cl1 -172(2) . . . . ? O11 Cl1 O12 N11 -145(5) . . . . ? C1 Cl1 O12 N11 5.2(13) . . . . ? Cl1 N11 C1 C6 17(3) . . . . ? O12 N11 C1 C6 -177.7(6) . . . . ? O11 N11 C1 C6 5.0(11) . . . . ? Cl1 N11 C1 C2 -165(3) . . . . ? O12 N11 C1 C2 -0.2(10) . . . . ? O11 N11 C1 C2 -177.5(7) . . . . ? O12 N11 C1 Cl1 165(4) . . . . ? O11 N11 C1 Cl1 -12(2) . . . . ? N11 Cl1 C1 C6 -164(3) . . . . ? O11 Cl1 C1 C6 -1.3(7) . . . . ? O12 Cl1 C1 C6 -175.7(3) . . . . ? N11 Cl1 C1 C2 16(3) . . . . ? O11 Cl1 C1 C2 179.1(6) . . . . ? O12 Cl1 C1 C2 4.7(4) . . . . ? O11 Cl1 C1 N11 163(3) . . . . ? O12 Cl1 C1 N11 -11(3) . . . . ? C6 C1 C2 C3 -1.0(4) . . . . ? N11 C1 C2 C3 -178.6(5) . . . . ? Cl1 C1 C2 C3 178.5(2) . . . . ? C1 C2 C3 C4 1.2(3) . . . . ? C2 C3 C4 C5 -1.3(3) . . . . ? C2 C3 C4 C7 179.6(2) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C7 C4 C5 C6 -179.7(2) . . . . ? C2 C1 C6 C5 0.9(4) . . . . ? N11 C1 C6 C5 178.2(5) . . . . ? Cl1 C1 C6 C5 -178.7(2) . . . . ? C4 C5 C6 C1 -1.0(3) . . . . ? C3 C4 C7 C17 -4.9(4) . . . . ? C5 C4 C7 C17 176.0(3) . . . . ? O1 Cl11 N1 O2 -172.3(10) . . . . ? C11 Cl11 N1 O2 167(3) . . . . ? O2 Cl11 N1 O1 172.3(10) . . . . ? C11 Cl11 N1 O1 -20(4) . . . . ? O1 Cl11 N1 C11 20(4) . . . . ? O2 Cl11 N1 C11 -167(3) . . . . ? O2 Cl11 O1 N1 -141(5) . . . . ? C11 Cl11 O1 N1 8.4(16) . . . . ? O2 N1 O1 Cl11 9.4(12) . . . . ? C11 N1 O1 Cl11 -168(2) . . . . ? O1 N1 O2 Cl11 -5.2(7) . . . . ? C11 N1 O2 Cl11 172(2) . . . . ? O1 Cl11 O2 N1 145(5) . . . . ? C11 Cl11 O2 N1 -5.2(13) . . . . ? Cl11 N1 C11 C16 -17(3) . . . . ? O2 N1 C11 C16 177.7(6) . . . . ? O1 N1 C11 C16 -5.0(11) . . . . ? Cl11 N1 C11 C12 165(3) . . . . ? O2 N1 C11 C12 0.2(10) . . . . ? O1 N1 C11 C12 177.5(7) . . . . ? O2 N1 C11 Cl11 -165(4) . . . . ? O1 N1 C11 Cl11 12(2) . . . . ? N1 Cl11 C11 C16 164(3) . . . . ? O1 Cl11 C11 C16 1.3(7) . . . . ? O2 Cl11 C11 C16 175.7(3) . . . . ? N1 Cl11 C11 C12 -16(3) . . . . ? O1 Cl11 C11 C12 -179.1(6) . . . . ? O2 Cl11 C11 C12 -4.7(4) . . . . ? O1 Cl11 C11 N1 -163(3) . . . . ? O2 Cl11 C11 N1 11(3) . . . . ? C16 C11 C12 C13 1.0(4) . . . . ? N1 C11 C12 C13 178.6(5) . . . . ? Cl11 C11 C12 C13 -178.5(2) . . . . ? C11 C12 C13 C14 -1.2(3) . . . . ? C12 C13 C14 C15 1.3(3) . . . . ? C12 C13 C14 C17 -179.6(2) . . . . ? C13 C14 C15 C16 -1.1(3) . . . . ? C17 C14 C15 C16 179.7(2) . . . . ? C12 C11 C16 C15 -0.9(4) . . . . ? N1 C11 C16 C15 -178.2(5) . . . . ? Cl11 C11 C16 C15 178.7(2) . . . . ? C14 C15 C16 C11 1.0(3) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 4.9(4) . . . . ? C15 C14 C17 C7 -176.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 27.80 _diffrn_measured_fraction_theta_full 0.904 _refine_diff_density_max 0.239 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.055 # start Validation Reply Form _vrf_ABSTM02_CNS-EtOAc-small-P21 ; PROBLEM: The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:22. ; _vrf_SYMMG02_CNS-EtOAc-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-EtOAc-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.90 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:22. ; _vrf_PLAT061_CNS-EtOAc-small-P21 ; PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.11 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:22. ; # end Validation Reply Form #===END data_CNS-EtOAc-big-A1 _database_code_depnum_ccdc_archive 'CCDC 761224' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'A 1' _symmetry_space_group_name_Hall 'A 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, y+1/2, z+1/2' _cell_length_a 3.9227(2) _cell_length_b 25.9528(7) _cell_length_c 24.5070(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.200(2) _cell_angle_gamma 90.00 _cell_volume 2491.05(16) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13806 _cell_measurement_theta_min 3.140 _cell_measurement_theta_max 25.809 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.094343 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4069 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0658 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.80 _reflns_number_total 3333 _reflns_number_gt 1553 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1125P)^2^+0.5936P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(2) _refine_ls_number_reflns 3333 _refine_ls_number_parameters 72 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1419 _refine_ls_R_factor_gt 0.0746 _refine_ls_wR_factor_ref 0.2417 _refine_ls_wR_factor_gt 0.1949 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1A Cl 0.3669 -0.2301 -0.0876 0.1162(8) Uani 0.453(10) 1 d P A 1 N1A N -0.3720 0.2086 0.0868 0.0845(14) Uani 0.453(10) 1 d P A 1 O1A O -0.3097 0.2493 0.0620 0.1264(17) Uani 0.453(10) 1 d P A 1 O2A O -0.5018 0.2067 0.1294 0.1111(13) Uani 0.453(10) 1 d P A 1 Cl1E Cl -0.3669 0.2301 0.0876 0.1162(8) Uani 0.547(10) 1 d P A 2 N1E N 0.3720 -0.2086 -0.0868 0.0845(14) Uani 0.547(10) 1 d P A 2 O1E O 0.3097 -0.2493 -0.0620 0.1264(17) Uani 0.547(10) 1 d P A 2 O2E O 0.5018 -0.2067 -0.1294 0.1111(13) Uani 0.547(10) 1 d P A 2 C1A C 0.2615 -0.1646 -0.0615 0.0704(6) Uani 1 1 d . A 2 C2A C 0.3166 -0.1194 -0.0898 0.0794(7) Uani 1 1 d . A 2 H2A H 0.4157 -0.1200 -0.1234 0.095 Uiso 1 1 calc R A 2 C3A C 0.2214 -0.0738 -0.0670 0.0756(7) Uani 1 1 d . A 2 H3A H 0.2534 -0.0433 -0.0860 0.091 Uiso 1 1 calc R A 2 C4A C 0.0796 -0.0715 -0.0168 0.0643(6) Uani 1 1 d . A 2 C5A C 0.0285 -0.1180 0.0103 0.0725(6) Uani 1 1 d . A 2 H5A H -0.0704 -0.1176 0.0439 0.087 Uiso 1 1 calc R A 2 C6A C 0.1213 -0.1646 -0.0118 0.0760(7) Uani 1 1 d . A 2 H6A H 0.0890 -0.1952 0.0069 0.091 Uiso 1 1 calc R A 2 C7A C -0.0246 -0.0233 0.0094 0.0724(6) Uani 1 1 d . A 2 H7A H -0.1341 -0.0262 0.0420 0.087 Uiso 1 1 calc R A 2 C11A C -0.2615 0.1646 0.0615 0.0704(6) Uani 1 1 d . A 2 C12A C -0.3166 0.1194 0.0898 0.0794(7) Uani 1 1 d . A 2 H12A H -0.4157 0.1200 0.1234 0.095 Uiso 1 1 calc R A 2 C13A C -0.2214 0.0738 0.0670 0.0756(7) Uani 1 1 d . A 2 H13A H -0.2534 0.0433 0.0860 0.091 Uiso 1 1 calc R A 2 C14A C -0.0796 0.0715 0.0168 0.0643(6) Uani 1 1 d . A 2 C15A C -0.0285 0.1180 -0.0103 0.0725(6) Uani 1 1 d . A 2 H15A H 0.0703 0.1176 -0.0439 0.087 Uiso 1 1 calc R A 2 C16A C -0.1213 0.1646 0.0118 0.0760(7) Uani 1 1 d . A 2 H16A H -0.0890 0.1953 -0.0069 0.091 Uiso 1 1 calc R A 2 C17A C 0.0246 0.0233 -0.0094 0.0724(6) Uani 1 1 d . A 2 H17A H 0.1341 0.0262 -0.0420 0.087 Uiso 1 1 calc R A 2 Cl1B Cl 0.3669 -0.2301 0.4124 0.1162(8) Uani 0.385(10) 1 d P B 3 N1B N -0.3720 0.2086 0.5868 0.0845(14) Uani 0.385(10) 1 d P B 3 O1B O -0.3097 0.2493 0.5620 0.1264(17) Uani 0.385(10) 1 d P B 3 O2B O -0.5018 0.2067 0.6294 0.1111(13) Uani 0.385(10) 1 d P B 3 Cl1F Cl -0.3669 0.2301 0.5876 0.1162(8) Uani 0.615(10) 1 d P B 4 N1F N 0.3720 -0.2086 0.4132 0.0845(14) Uani 0.615(10) 1 d P B 4 O1F O 0.3097 -0.2493 0.4380 0.1264(17) Uani 0.615(10) 1 d P B 4 O2F O 0.5018 -0.2067 0.3706 0.1111(13) Uani 0.615(10) 1 d P B 4 C1B C 0.2615 -0.1646 0.4385 0.0704(6) Uani 1 1 d . B 4 C2B C 0.3166 -0.1194 0.4102 0.0794(7) Uani 1 1 d . B 4 H2B H 0.4157 -0.1200 0.3766 0.095 Uiso 1 1 calc R B 4 C3B C 0.2214 -0.0738 0.4330 0.0756(7) Uani 1 1 d . B 4 H3B H 0.2534 -0.0433 0.4140 0.091 Uiso 1 1 calc R B 4 C4B C 0.0796 -0.0715 0.4832 0.0643(6) Uani 1 1 d . B 4 C5B C 0.0285 -0.1180 0.5103 0.0725(6) Uani 1 1 d . B 4 H5B H -0.0704 -0.1176 0.5439 0.087 Uiso 1 1 calc R B 4 C6B C 0.1213 -0.1646 0.4882 0.0760(7) Uani 1 1 d . B 4 H6B H 0.0890 -0.1952 0.5069 0.091 Uiso 1 1 calc R B 4 C7B C -0.0246 -0.0233 0.5094 0.0724(6) Uani 1 1 d . B 4 H7B H -0.1341 -0.0262 0.5420 0.087 Uiso 1 1 calc R B 4 C11B C -0.2615 0.1646 0.5615 0.0704(6) Uani 1 1 d . B 4 C12B C -0.3166 0.1194 0.5898 0.0794(7) Uani 1 1 d . B 4 H12B H -0.4157 0.1200 0.6234 0.095 Uiso 1 1 calc R B 4 C13B C -0.2214 0.0738 0.5670 0.0756(7) Uani 1 1 d . B 4 H13B H -0.2534 0.0433 0.5860 0.091 Uiso 1 1 calc R B 4 C14B C -0.0796 0.0715 0.5168 0.0643(6) Uani 1 1 d . B 4 C15B C -0.0285 0.1180 0.4897 0.0725(6) Uani 1 1 d . B 4 H15B H 0.0703 0.1176 0.4561 0.087 Uiso 1 1 calc R B 4 C16B C -0.1213 0.1646 0.5118 0.0760(7) Uani 1 1 d . B 4 H16B H -0.0890 0.1953 0.4931 0.091 Uiso 1 1 calc R B 4 C17B C 0.0246 0.0233 0.4906 0.0724(6) Uani 1 1 d . B 4 H17B H 0.1341 0.0262 0.4580 0.087 Uiso 1 1 calc R B 4 Cl1C Cl -0.3669 0.0199 0.3376 0.1162(8) Uani 0.400(6) 1 d P C 5 N1C N 0.3720 0.4586 0.1632 0.0845(14) Uani 0.400(6) 1 d P C 5 O1C O 0.3097 0.4993 0.1880 0.1264(17) Uani 0.400(6) 1 d P C 5 O2C O 0.5018 0.4567 0.1206 0.1111(13) Uani 0.400(6) 1 d P C 5 Cl1G Cl 0.3669 0.4801 0.1624 0.1162(8) Uani 0.600(6) 1 d P C 6 N1G N -0.3720 0.0414 0.3368 0.0845(14) Uani 0.600(6) 1 d P C 6 O1G O -0.3097 0.0007 0.3120 0.1264(17) Uani 0.600(6) 1 d P C 6 O2G O -0.5018 0.0433 0.3794 0.1111(13) Uani 0.600(6) 1 d P C 6 C1C C -0.2615 0.0854 0.3115 0.0704(6) Uani 1 1 d . C 6 C2C C -0.3166 0.1306 0.3398 0.0794(7) Uani 1 1 d . C 6 H2C H -0.4157 0.1300 0.3734 0.095 Uiso 1 1 calc R C 6 C3C C -0.2214 0.1762 0.3170 0.0756(7) Uani 1 1 d . C 6 H3C H -0.2534 0.2067 0.3360 0.091 Uiso 1 1 calc R C 6 C4C C -0.0796 0.1785 0.2668 0.0643(6) Uani 1 1 d . C 6 C5C C -0.0285 0.1320 0.2397 0.0725(6) Uani 1 1 d . C 6 H5C H 0.0703 0.1324 0.2061 0.087 Uiso 1 1 calc R C 6 C6C C -0.1213 0.0854 0.2618 0.0760(7) Uani 1 1 d . C 6 H6C H -0.0890 0.0548 0.2431 0.091 Uiso 1 1 calc R C 6 C7C C 0.0246 0.2267 0.2406 0.0724(6) Uani 1 1 d . C 6 H7C H 0.1341 0.2238 0.2080 0.087 Uiso 1 1 calc R C 6 C11C C 0.2615 0.4146 0.1885 0.0704(6) Uani 1 1 d . C 6 C12C C 0.3166 0.3694 0.1602 0.0794(7) Uani 1 1 d . C 6 H12C H 0.4157 0.3700 0.1266 0.095 Uiso 1 1 calc R C 6 C13C C 0.2214 0.3238 0.1830 0.0756(7) Uani 1 1 d . C 6 H13C H 0.2534 0.2933 0.1640 0.091 Uiso 1 1 calc R C 6 C14C C 0.0796 0.3215 0.2332 0.0643(6) Uani 1 1 d . C 6 C15C C 0.0285 0.3680 0.2603 0.0725(6) Uani 1 1 d . C 6 H15C H -0.0704 0.3676 0.2939 0.087 Uiso 1 1 calc R C 6 C16C C 0.1213 0.4146 0.2382 0.0760(7) Uani 1 1 d . C 6 H16C H 0.0890 0.4452 0.2569 0.091 Uiso 1 1 calc R C 6 C17C C -0.0246 0.2733 0.2594 0.0724(6) Uani 1 1 d . C 6 H17C H -0.1341 0.2762 0.2920 0.087 Uiso 1 1 calc R C 6 Cl1D Cl -0.3669 0.0199 -0.1624 0.1162(8) Uani 0.251(6) 1 d P D 7 N1D N 0.3720 0.4586 -0.3368 0.0845(14) Uani 0.251(6) 1 d P D 7 O1D O 0.3097 0.4993 -0.3120 0.1264(17) Uani 0.251(6) 1 d P D 7 O2D O 0.5018 0.4567 -0.3794 0.1111(13) Uani 0.251(6) 1 d P D 7 Cl1H Cl 0.3669 0.4801 -0.3376 0.1162(8) Uani 0.749(6) 1 d P D 8 N1H N -0.3720 0.0414 -0.1632 0.0845(14) Uani 0.749(6) 1 d P D 8 O1H O -0.3097 0.0007 -0.1880 0.1264(17) Uani 0.749(6) 1 d P D 8 O2H O -0.5018 0.0433 -0.1206 0.1111(13) Uani 0.749(6) 1 d P D 8 C1D C -0.2615 0.0854 -0.1885 0.0704(6) Uani 1 1 d . D 8 C2D C -0.3166 0.1306 -0.1602 0.0794(7) Uani 1 1 d . D 8 H2D H -0.4157 0.1300 -0.1266 0.095 Uiso 1 1 calc R D 8 C3D C -0.2214 0.1762 -0.1830 0.0756(7) Uani 1 1 d . D 8 H3D H -0.2534 0.2067 -0.1640 0.091 Uiso 1 1 calc R D 8 C4D C -0.0796 0.1785 -0.2332 0.0643(6) Uani 1 1 d . D 8 C5D C -0.0285 0.1320 -0.2603 0.0725(6) Uani 1 1 d . D 8 H5D H 0.0703 0.1324 -0.2939 0.087 Uiso 1 1 calc R D 8 C6D C -0.1213 0.0854 -0.2382 0.0760(7) Uani 1 1 d . D 8 H6D H -0.0890 0.0548 -0.2569 0.091 Uiso 1 1 calc R D 8 C7D C 0.0246 0.2267 -0.2594 0.0724(6) Uani 1 1 d . D 8 H7D H 0.1341 0.2238 -0.2920 0.087 Uiso 1 1 calc R D 8 C11D C 0.2615 0.4146 -0.3115 0.0704(6) Uani 1 1 d . D 8 C12D C 0.3166 0.3694 -0.3398 0.0794(7) Uani 1 1 d . D 8 H12D H 0.4157 0.3700 -0.3734 0.095 Uiso 1 1 calc R D 8 C13D C 0.2214 0.3238 -0.3170 0.0756(7) Uani 1 1 d . D 8 H13D H 0.2534 0.2933 -0.3360 0.091 Uiso 1 1 calc R D 8 C14D C 0.0796 0.3215 -0.2668 0.0643(6) Uani 1 1 d . D 8 C15D C 0.0285 0.3680 -0.2397 0.0725(6) Uani 1 1 d . D 8 H15D H -0.0704 0.3676 -0.2061 0.087 Uiso 1 1 calc R D 8 C16D C 0.1213 0.4146 -0.2618 0.0760(7) Uani 1 1 d . D 8 H16D H 0.0890 0.4452 -0.2431 0.091 Uiso 1 1 calc R D 8 C17D C -0.0246 0.2733 -0.2406 0.0724(6) Uani 1 1 d . D 8 H17D H -0.1341 0.2762 -0.2080 0.087 Uiso 1 1 calc R D 8 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1A 0.1235(14) 0.0802(13) 0.1445(18) -0.0474(12) 0.0032(12) 0.0188(9) N1A 0.091(3) 0.057(3) 0.103(4) -0.005(2) -0.019(3) -0.0059(19) O1A 0.180(4) 0.054(2) 0.148(4) 0.008(2) 0.031(3) 0.016(2) O2A 0.159(4) 0.078(2) 0.099(3) -0.026(2) 0.032(2) 0.014(2) Cl1E 0.1235(14) 0.0802(13) 0.1445(18) -0.0474(12) 0.0032(12) 0.0188(9) N1E 0.091(3) 0.057(3) 0.103(4) -0.005(2) -0.019(3) -0.0059(19) O1E 0.180(4) 0.054(2) 0.148(4) 0.008(2) 0.031(3) 0.016(2) O2E 0.159(4) 0.078(2) 0.099(3) -0.026(2) 0.032(2) 0.014(2) C1A 0.0624(13) 0.0709(15) 0.0769(15) -0.0158(11) -0.0042(10) 0.0045(10) C2A 0.0779(15) 0.0947(19) 0.0661(15) -0.0025(12) 0.0078(12) 0.0013(12) C3A 0.0725(14) 0.0724(15) 0.0820(16) 0.0100(12) 0.0036(11) -0.0039(11) C4A 0.0580(12) 0.0693(14) 0.0649(14) -0.0046(10) -0.0022(10) 0.0013(9) C5A 0.0786(15) 0.0733(15) 0.0657(13) 0.0046(11) 0.0052(10) -0.0036(11) C6A 0.0815(15) 0.0621(14) 0.0839(17) -0.0001(12) 0.0005(12) 0.0037(11) C7A 0.0702(13) 0.0731(14) 0.0739(14) 0.0055(11) 0.0025(10) -0.0034(11) C11A 0.0624(13) 0.0709(15) 0.0769(15) -0.0158(11) -0.0042(10) 0.0045(10) C12A 0.0779(15) 0.0947(19) 0.0661(15) -0.0025(12) 0.0078(12) 0.0013(12) C13A 0.0725(14) 0.0724(15) 0.0820(16) 0.0100(12) 0.0036(11) -0.0039(11) C14A 0.0580(12) 0.0693(14) 0.0649(14) -0.0046(10) -0.0022(10) 0.0013(9) C15A 0.0786(15) 0.0733(15) 0.0657(13) 0.0046(11) 0.0052(10) -0.0036(11) C16A 0.0815(15) 0.0621(14) 0.0839(17) -0.0001(12) 0.0005(12) 0.0037(11) C17A 0.0702(13) 0.0731(14) 0.0739(14) 0.0055(11) 0.0025(10) -0.0034(11) Cl1B 0.1235(14) 0.0802(13) 0.1445(18) -0.0474(12) 0.0032(12) 0.0188(9) N1B 0.091(3) 0.057(3) 0.103(4) -0.005(2) -0.019(3) -0.0059(19) O1B 0.180(4) 0.054(2) 0.148(4) 0.008(2) 0.031(3) 0.016(2) O2B 0.159(4) 0.078(2) 0.099(3) -0.026(2) 0.032(2) 0.014(2) Cl1F 0.1235(14) 0.0802(13) 0.1445(18) -0.0474(12) 0.0032(12) 0.0188(9) N1F 0.091(3) 0.057(3) 0.103(4) -0.005(2) -0.019(3) -0.0059(19) O1F 0.180(4) 0.054(2) 0.148(4) 0.008(2) 0.031(3) 0.016(2) O2F 0.159(4) 0.078(2) 0.099(3) -0.026(2) 0.032(2) 0.014(2) C1B 0.0624(13) 0.0709(15) 0.0769(15) -0.0158(11) -0.0042(10) 0.0045(10) C2B 0.0779(15) 0.0947(19) 0.0661(15) -0.0025(12) 0.0078(12) 0.0013(12) C3B 0.0725(14) 0.0724(15) 0.0820(16) 0.0100(12) 0.0036(11) -0.0039(11) C4B 0.0580(12) 0.0693(14) 0.0649(14) -0.0046(10) -0.0022(10) 0.0013(9) C5B 0.0786(15) 0.0733(15) 0.0657(13) 0.0046(11) 0.0052(10) -0.0036(11) C6B 0.0815(15) 0.0621(14) 0.0839(17) -0.0001(12) 0.0005(12) 0.0037(11) C7B 0.0702(13) 0.0731(14) 0.0739(14) 0.0055(11) 0.0025(10) -0.0034(11) C11B 0.0624(13) 0.0709(15) 0.0769(15) -0.0158(11) -0.0042(10) 0.0045(10) C12B 0.0779(15) 0.0947(19) 0.0661(15) -0.0025(12) 0.0078(12) 0.0013(12) C13B 0.0725(14) 0.0724(15) 0.0820(16) 0.0100(12) 0.0036(11) -0.0039(11) C14B 0.0580(12) 0.0693(14) 0.0649(14) -0.0046(10) -0.0022(10) 0.0013(9) C15B 0.0786(15) 0.0733(15) 0.0657(13) 0.0046(11) 0.0052(10) -0.0036(11) C16B 0.0815(15) 0.0621(14) 0.0839(17) -0.0001(12) 0.0005(12) 0.0037(11) C17B 0.0702(13) 0.0731(14) 0.0739(14) 0.0055(11) 0.0025(10) -0.0034(11) Cl1C 0.1235(14) 0.0802(13) 0.1445(18) 0.0474(12) 0.0032(12) -0.0188(9) N1C 0.091(3) 0.057(3) 0.103(4) 0.005(2) -0.019(3) 0.0059(19) O1C 0.180(4) 0.054(2) 0.148(4) -0.008(2) 0.031(3) -0.016(2) O2C 0.159(4) 0.078(2) 0.099(3) 0.026(2) 0.032(2) -0.014(2) Cl1G 0.1235(14) 0.0802(13) 0.1445(18) 0.0474(12) 0.0032(12) -0.0188(9) N1G 0.091(3) 0.057(3) 0.103(4) 0.005(2) -0.019(3) 0.0059(19) O1G 0.180(4) 0.054(2) 0.148(4) -0.008(2) 0.031(3) -0.016(2) O2G 0.159(4) 0.078(2) 0.099(3) 0.026(2) 0.032(2) -0.014(2) C1C 0.0624(13) 0.0709(15) 0.0769(15) 0.0158(11) -0.0042(10) -0.0045(10) C2C 0.0779(15) 0.0947(19) 0.0661(15) 0.0025(12) 0.0078(12) -0.0013(12) C3C 0.0725(14) 0.0724(15) 0.0820(16) -0.0100(12) 0.0036(11) 0.0039(11) C4C 0.0580(12) 0.0693(14) 0.0649(14) 0.0046(10) -0.0022(10) -0.0013(9) C5C 0.0786(15) 0.0733(15) 0.0657(13) -0.0046(11) 0.0052(10) 0.0036(11) C6C 0.0815(15) 0.0621(14) 0.0839(17) 0.0001(12) 0.0005(12) -0.0037(11) C7C 0.0702(13) 0.0731(14) 0.0739(14) -0.0055(11) 0.0025(10) 0.0034(11) C11C 0.0624(13) 0.0709(15) 0.0769(15) 0.0158(11) -0.0042(10) -0.0045(10) C12C 0.0779(15) 0.0947(19) 0.0661(15) 0.0025(12) 0.0078(12) -0.0013(12) C13C 0.0725(14) 0.0724(15) 0.0820(16) -0.0100(12) 0.0036(11) 0.0039(11) C14C 0.0580(12) 0.0693(14) 0.0649(14) 0.0046(10) -0.0022(10) -0.0013(9) C15C 0.0786(15) 0.0733(15) 0.0657(13) -0.0046(11) 0.0052(10) 0.0036(11) C16C 0.0815(15) 0.0621(14) 0.0839(17) 0.0001(12) 0.0005(12) -0.0037(11) C17C 0.0702(13) 0.0731(14) 0.0739(14) -0.0055(11) 0.0025(10) 0.0034(11) Cl1D 0.1235(14) 0.0802(13) 0.1445(18) 0.0474(12) 0.0032(12) -0.0188(9) N1D 0.091(3) 0.057(3) 0.103(4) 0.005(2) -0.019(3) 0.0059(19) O1D 0.180(4) 0.054(2) 0.148(4) -0.008(2) 0.031(3) -0.016(2) O2D 0.159(4) 0.078(2) 0.099(3) 0.026(2) 0.032(2) -0.014(2) Cl1H 0.1235(14) 0.0802(13) 0.1445(18) 0.0474(12) 0.0032(12) -0.0188(9) N1H 0.091(3) 0.057(3) 0.103(4) 0.005(2) -0.019(3) 0.0059(19) O1H 0.180(4) 0.054(2) 0.148(4) -0.008(2) 0.031(3) -0.016(2) O2H 0.159(4) 0.078(2) 0.099(3) 0.026(2) 0.032(2) -0.014(2) C1D 0.0624(13) 0.0709(15) 0.0769(15) 0.0158(11) -0.0042(10) -0.0045(10) C2D 0.0779(15) 0.0947(19) 0.0661(15) 0.0025(12) 0.0078(12) -0.0013(12) C3D 0.0725(14) 0.0724(15) 0.0820(16) -0.0100(12) 0.0036(11) 0.0039(11) C4D 0.0580(12) 0.0693(14) 0.0649(14) 0.0046(10) -0.0022(10) -0.0013(9) C5D 0.0786(15) 0.0733(15) 0.0657(13) -0.0046(11) 0.0052(10) 0.0036(11) C6D 0.0815(15) 0.0621(14) 0.0839(17) 0.0001(12) 0.0005(12) -0.0037(11) C7D 0.0702(13) 0.0731(14) 0.0739(14) -0.0055(11) 0.0025(10) 0.0034(11) C11D 0.0624(13) 0.0709(15) 0.0769(15) 0.0158(11) -0.0042(10) -0.0045(10) C12D 0.0779(15) 0.0947(19) 0.0661(15) 0.0025(12) 0.0078(12) -0.0013(12) C13D 0.0725(14) 0.0724(15) 0.0820(16) -0.0100(12) 0.0036(11) 0.0039(11) C14D 0.0580(12) 0.0693(14) 0.0649(14) 0.0046(10) -0.0022(10) -0.0013(9) C15D 0.0786(15) 0.0733(15) 0.0657(13) -0.0046(11) 0.0052(10) 0.0036(11) C16D 0.0815(15) 0.0621(14) 0.0839(17) 0.0001(12) 0.0005(12) -0.0037(11) C17D 0.0702(13) 0.0731(14) 0.0739(14) -0.0055(11) 0.0025(10) 0.0034(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1A O2A 1.1878 . ? N1A O1A 1.2484 . ? Cl1E C11A 1.8697 . ? N1E O2E 1.1878 . ? N1E O1E 1.2484 . ? N1E C1A 1.3799 . ? C1A C6A 1.3655 . ? C1A C2A 1.3855 . ? C2A C3A 1.3699 . ? C2A H2A 0.9300 . ? C3A C4A 1.3798 . ? C3A H3A 0.9300 . ? C4A C5A 1.3969 . ? C4A C7A 1.4734 . ? C5A C6A 1.3808 . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? C7A C17A 1.3148 . ? C7A H7A 0.9300 . ? C11A C16A 1.3652 . ? C11A C12A 1.3858 . ? C12A C13A 1.3698 . ? C12A H12A 0.9300 . ? C13A C14A 1.3796 . ? C13A H13A 0.9300 . ? C14A C15A 1.3971 . ? C14A C17A 1.4737 . ? C15A C16A 1.3808 . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? C17A H17A 0.9300 . ? N1B O2B 1.1878 . ? N1B O1B 1.2484 . ? Cl1F C11B 1.8697 . ? N1F O2F 1.1878 . ? N1F O1F 1.2484 . ? N1F C1B 1.3799 . ? C1B C6B 1.3655 . ? C1B C2B 1.3855 . ? C2B C3B 1.3699 . ? C2B H2B 0.9300 . ? C3B C4B 1.3798 . ? C3B H3B 0.9300 . ? C4B C5B 1.3969 . ? C4B C7B 1.4734 . ? C5B C6B 1.3808 . ? C5B H5B 0.9300 . ? C6B H6B 0.9300 . ? C7B C17B 1.3148 . ? C7B H7B 0.9300 . ? C11B C16B 1.3652 . ? C11B C12B 1.3858 . ? C12B C13B 1.3698 . ? C12B H12B 0.9300 . ? C13B C14B 1.3796 . ? C13B H13B 0.9300 . ? C14B C15B 1.3971 . ? C14B C17B 1.4737 . ? C15B C16B 1.3808 . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? C17B H17B 0.9300 . ? N1C O2C 1.1879 . ? N1C O1C 1.2483 . ? Cl1G C11C 1.8700 . ? N1G O2G 1.1877 . ? N1G O1G 1.2484 . ? N1G C1C 1.3800 . ? C1C C6C 1.3652 . ? C1C C2C 1.3856 . ? C2C C3C 1.3699 . ? C2C H2C 0.9300 . ? C3C C4C 1.3796 . ? C3C H3C 0.9300 . ? C4C C5C 1.3970 . ? C4C C7C 1.4737 . ? C5C C6C 1.3809 . ? C5C H5C 0.9300 . ? C6C H6C 0.9300 . ? C7C C17C 1.3143 . ? C7C H7C 0.9300 . ? C11C C16C 1.3652 . ? C11C C12C 1.3855 . ? C12C C13C 1.3695 . ? C12C H12C 0.9300 . ? C13C C14C 1.3796 . ? C13C H13C 0.9300 . ? C14C C15C 1.3969 . ? C14C C17C 1.4740 . ? C15C C16C 1.3804 . ? C15C H15C 0.9300 . ? C16C H16C 0.9300 . ? C17C H17C 0.9300 . ? N1D O2D 1.1879 . ? N1D O1D 1.2483 . ? Cl1H C11D 1.8700 . ? N1H O2H 1.1877 . ? N1H O1H 1.2484 . ? N1H C1D 1.3800 . ? C1D C6D 1.3652 . ? C1D C2D 1.3856 . ? C2D C3D 1.3699 . ? C2D H2D 0.9300 . ? C3D C4D 1.3796 . ? C3D H3D 0.9300 . ? C4D C5D 1.3970 . ? C4D C7D 1.4737 . ? C5D C6D 1.3809 . ? C5D H5D 0.9300 . ? C6D H6D 0.9300 . ? C7D C17D 1.3143 . ? C7D H7D 0.9300 . ? C11D C16D 1.3652 . ? C11D C12D 1.3855 . ? C12D C13D 1.3695 . ? C12D H12D 0.9300 . ? C13D C14D 1.3796 . ? C13D H13D 0.9300 . ? C14D C15D 1.3969 . ? C14D C17D 1.4740 . ? C15D C16D 1.3804 . ? C15D H15D 0.9300 . ? C16D H16D 0.9300 . ? C17D H17D 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2A N1A O1A 124.610(1) . . ? O2E N1E O1E 124.593(2) . . ? O2E N1E C1A 121.369(2) . . ? O1E N1E C1A 113.974(2) . . ? C6A C1A N1E 123.633(2) . . ? C6A C1A C2A 121.814(2) . . ? N1E C1A C2A 114.504(2) . . ? C3A C2A C1A 118.365(2) . . ? C3A C2A H2A 120.8 . . ? C1A C2A H2A 120.8 . . ? C2A C3A C4A 122.211(1) . . ? C2A C3A H3A 118.9 . . ? C4A C3A H3A 118.9 . . ? C3A C4A C5A 117.505(1) . . ? C3A C4A C7A 124.101(1) . . ? C5A C4A C7A 118.388(2) . . ? C6A C5A C4A 121.524(2) . . ? C6A C5A H5A 119.2 . . ? C4A C5A H5A 119.2 . . ? C1A C6A C5A 118.563(2) . . ? C1A C6A H6A 120.7 . . ? C5A C6A H6A 120.7 . . ? C17A C7A C4A 125.349(2) . . ? C17A C7A H7A 117.3 . . ? C4A C7A H7A 117.3 . . ? C16A C11A C12A 121.817(1) . . ? C16A C11A Cl1E 114.443(1) . . ? C12A C11A Cl1E 123.739(1) . . ? C13A C12A C11A 118.354(2) . . ? C13A C12A H12A 120.8 . . ? C11A C12A H12A 120.8 . . ? C12A C13A C14A 122.219(1) . . ? C12A C13A H13A 118.9 . . ? C14A C13A H13A 118.9 . . ? C13A C14A C15A 117.510(1) . . ? C13A C14A C17A 124.106(2) . . ? C15A C14A C17A 118.378(2) . . ? C16A C15A C14A 121.509(2) . . ? C16A C15A H15A 119.2 . . ? C14A C15A H15A 119.2 . . ? C11A C16A C15A 118.573(1) . . ? C11A C16A H16A 120.7 . . ? C15A C16A H16A 120.7 . . ? C7A C17A C14A 125.344(1) . . ? C7A C17A H17A 117.3 . . ? C14A C17A H17A 117.3 . . ? O2B N1B O1B 124.610(1) . . ? O2F N1F O1F 124.593(2) . . ? O2F N1F C1B 121.369(1) . . ? O1F N1F C1B 113.974(3) . . ? C6B C1B N1F 123.633(2) . . ? C6B C1B C2B 121.814(1) . . ? N1F C1B C2B 114.504(2) . . ? C3B C2B C1B 118.365(3) . . ? C3B C2B H2B 120.8 . . ? C1B C2B H2B 120.8 . . ? C2B C3B C4B 122.211(2) . . ? C2B C3B H3B 118.9 . . ? C4B C3B H3B 118.9 . . ? C3B C4B C5B 117.505(2) . . ? C3B C4B C7B 124.101(1) . . ? C5B C4B C7B 118.388(2) . . ? C6B C5B C4B 121.524(3) . . ? C6B C5B H5B 119.2 . . ? C4B C5B H5B 119.2 . . ? C1B C6B C5B 118.563(1) . . ? C1B C6B H6B 120.7 . . ? C5B C6B H6B 120.7 . . ? C17B C7B C4B 125.349(2) . . ? C17B C7B H7B 117.3 . . ? C4B C7B H7B 117.3 . . ? C16B C11B C12B 121.817(1) . . ? C16B C11B Cl1F 114.443(1) . . ? C12B C11B Cl1F 123.739(1) . . ? C13B C12B C11B 118.354(2) . . ? C13B C12B H12B 120.8 . . ? C11B C12B H12B 120.8 . . ? C12B C13B C14B 122.219(1) . . ? C12B C13B H13B 118.9 . . ? C14B C13B H13B 118.9 . . ? C13B C14B C15B 117.510(1) . . ? C13B C14B C17B 124.106(1) . . ? C15B C14B C17B 118.378(2) . . ? C16B C15B C14B 121.509(2) . . ? C16B C15B H15B 119.2 . . ? C14B C15B H15B 119.2 . . ? C11B C16B C15B 118.573(1) . . ? C11B C16B H16B 120.7 . . ? C15B C16B H16B 120.7 . . ? C7B C17B C14B 125.344(2) . . ? C7B C17B H17B 117.3 . . ? C14B C17B H17B 117.3 . . ? O2C N1C O1C 124.604(1) . . ? O2G N1G O1G 124.592(1) . . ? O2G N1G C1C 121.379(2) . . ? O1G N1G C1C 113.966(2) . . ? C6C C1C N1G 123.643(1) . . ? C6C C1C C2C 121.821(1) . . ? N1G C1C C2C 114.488(2) . . ? C3C C2C C1C 118.354(2) . . ? C3C C2C H2C 120.8 . . ? C1C C2C H2C 120.8 . . ? C2C C3C C4C 122.215(1) . . ? C2C C3C H3C 118.9 . . ? C4C C3C H3C 118.9 . . ? C3C C4C C5C 117.513(1) . . ? C3C C4C C7C 124.1 . . ? C5C C4C C7C 118.376(2) . . ? C6C C5C C4C 121.509(2) . . ? C6C C5C H5C 119.2 . . ? C4C C5C H5C 119.2 . . ? C1C C6C C5C 118.571(1) . . ? C1C C6C H6C 120.7 . . ? C5C C6C H6C 120.7 . . ? C17C C7C C4C 125.336(2) . . ? C17C C7C H7C 117.3 . . ? C4C C7C H7C 117.3 . . ? C16C C11C C12C 121.824(2) . . ? C16C C11C Cl1G 114.440(1) . . ? C12C C11C Cl1G 123.735(2) . . ? C13C C12C C11C 118.340(1) . . ? C13C C12C H12C 120.8 . . ? C11C C12C H12C 120.8 . . ? C12C C13C C14C 122.230(2) . . ? C12C C13C H13C 118.9 . . ? C14C C13C H13C 118.9 . . ? C13C C14C C15C 117.501(2) . . ? C13C C14C C17C 124.1 . . ? C15C C14C C17C 118.401(2) . . ? C16C C15C C14C 121.513(2) . . ? C16C C15C H15C 119.2 . . ? C14C C15C H15C 119.2 . . ? C11C C16C C15C 118.574(2) . . ? C11C C16C H16C 120.7 . . ? C15C C16C H16C 120.7 . . ? C7C C17C C14C 125.355(2) . . ? C7C C17C H17C 117.3 . . ? C14C C17C H17C 117.3 . . ? O2D N1D O1D 124.604(2) . . ? O2H N1H O1H 124.592(1) . . ? O2H N1H C1D 121.379(1) . . ? O1H N1H C1D 113.966(2) . . ? C6D C1D N1H 123.643(1) . . ? C6D C1D C2D 121.821(1) . . ? N1H C1D C2D 114.488(2) . . ? C3D C2D C1D 118.354(2) . . ? C3D C2D H2D 120.8 . . ? C1D C2D H2D 120.8 . . ? C2D C3D C4D 122.215(1) . . ? C2D C3D H3D 118.9 . . ? C4D C3D H3D 118.9 . . ? C3D C4D C5D 117.513(2) . . ? C3D C4D C7D 124.106(2) . . ? C5D C4D C7D 118.376(2) . . ? C6D C5D C4D 121.509(2) . . ? C6D C5D H5D 119.2 . . ? C4D C5D H5D 119.2 . . ? C1D C6D C5D 118.571(1) . . ? C1D C6D H6D 120.7 . . ? C5D C6D H6D 120.7 . . ? C17D C7D C4D 125.336(2) . . ? C17D C7D H7D 117.3 . . ? C4D C7D H7D 117.3 . . ? C16D C11D C12D 121.824(1) . . ? C16D C11D Cl1H 114.440(1) . . ? C12D C11D Cl1H 123.735(2) . . ? C13D C12D C11D 118.340(2) . . ? C13D C12D H12D 120.8 . . ? C11D C12D H12D 120.8 . . ? C12D C13D C14D 122.231(2) . . ? C12D C13D H13D 118.9 . . ? C14D C13D H13D 118.9 . . ? C13D C14D C15D 117.501(2) . . ? C13D C14D C17D 124.092(2) . . ? C15D C14D C17D 118.401(2) . . ? C16D C15D C14D 121.513(2) . . ? C16D C15D H15D 119.2 . . ? C14D C15D H15D 119.2 . . ? C11D C16D C15D 118.574(2) . . ? C11D C16D H16D 120.7 . . ? C15D C16D H16D 120.7 . . ? C7D C17D C14D 125.355(2) . . ? C7D C17D H17D 117.3 . . ? C14D C17D H17D 117.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2E N1E C1A C6A -177.7 . . . . ? O1E N1E C1A C6A 5.0 . . . . ? O2E N1E C1A C2A -0.3 . . . . ? O1E N1E C1A C2A -177.5 . . . . ? C6A C1A C2A C3A -1.1 . . . . ? N1E C1A C2A C3A -178.6 . . . . ? C1A C2A C3A C4A 1.2 . . . . ? C2A C3A C4A C5A -1.3 . . . . ? C2A C3A C4A C7A 179.6 . . . . ? C3A C4A C5A C6A 1.1 . . . . ? C7A C4A C5A C6A -179.7 . . . . ? N1E C1A C6A C5A 178.2 . . . . ? C2A C1A C6A C5A 0.9 . . . . ? C4A C5A C6A C1A -1.0 . . . . ? C3A C4A C7A C17A -5.0 . . . . ? C5A C4A C7A C17A 176.0 . . . . ? C16A C11A C12A C13A 1.0 . . . . ? Cl1E C11A C12A C13A -178.5 . . . . ? C11A C12A C13A C14A -1.2 . . . . ? C12A C13A C14A C15A 1.3 . . . . ? C12A C13A C14A C17A -179.6 . . . . ? C13A C14A C15A C16A -1.1 . . . . ? C17A C14A C15A C16A 179.7 . . . . ? C12A C11A C16A C15A -0.9 . . . . ? Cl1E C11A C16A C15A 178.7 . . . . ? C14A C15A C16A C11A 0.9 . . . . ? C4A C7A C17A C14A -180.0 . . . . ? C13A C14A C17A C7A 4.9 . . . . ? C15A C14A C17A C7A -175.9 . . . . ? O2F N1F C1B C6B -177.7 . . . . ? O1F N1F C1B C6B 5.045(1) . . . . ? O2F N1F C1B C2B -0.3 . . . . ? O1F N1F C1B C2B -177.5 . . . . ? C6B C1B C2B C3B -1.1 . . . . ? N1F C1B C2B C3B -178.6 . . . . ? C1B C2B C3B C4B 1.2 . . . . ? C2B C3B C4B C5B -1.3 . . . . ? C2B C3B C4B C7B 179.6 . . . . ? C3B C4B C5B C6B 1.1 . . . . ? C7B C4B C5B C6B -179.7 . . . . ? N1F C1B C6B C5B 178.2 . . . . ? C2B C1B C6B C5B 0.9 . . . . ? C4B C5B C6B C1B -1.0 . . . . ? C3B C4B C7B C17B -5.0 . . . . ? C5B C4B C7B C17B 175.952(1) . . . . ? C16B C11B C12B C13B 1.0 . . . . ? Cl1F C11B C12B C13B -178.5 . . . . ? C11B C12B C13B C14B -1.2 . . . . ? C12B C13B C14B C15B 1.3 . . . . ? C12B C13B C14B C17B -179.6 . . . . ? C13B C14B C15B C16B -1.1 . . . . ? C17B C14B C15B C16B 179.7 . . . . ? C12B C11B C16B C15B -0.9 . . . . ? Cl1F C11B C16B C15B 178.7 . . . . ? C14B C15B C16B C11B 0.9 . . . . ? C4B C7B C17B C14B -180.0 . . . . ? C13B C14B C17B C7B 4.9 . . . . ? C15B C14B C17B C7B -175.9 . . . . ? O2G N1G C1C C6C -177.7 . . . . ? O1G N1G C1C C6C 5.024(1) . . . . ? O2G N1G C1C C2C -0.2 . . . . ? O1G N1G C1C C2C -177.5 . . . . ? C6C C1C C2C C3C -1.0 . . . . ? N1G C1C C2C C3C -178.6 . . . . ? C1C C2C C3C C4C 1.230(1) . . . . ? C2C C3C C4C C5C -1.262(2) . . . . ? C2C C3C C4C C7C 179.618(1) . . . . ? C3C C4C C5C C6C 1.104(1) . . . . ? C7C C4C C5C C6C -179.7 . . . . ? N1G C1C C6C C5C 178.222(1) . . . . ? C2C C1C C6C C5C 0.894(1) . . . . ? C4C C5C C6C C1C -0.9 . . . . ? C3C C4C C7C C17C -4.9 . . . . ? C5C C4C C7C C17C 175.9 . . . . ? C16C C11C C12C C13C 1.0 . . . . ? Cl1G C11C C12C C13C -178.5 . . . . ? C11C C12C C13C C14C -1.2 . . . . ? C12C C13C C14C C15C 1.3 . . . . ? C12C C13C C14C C17C -179.6 . . . . ? C13C C14C C15C C16C -1.1 . . . . ? C17C C14C C15C C16C 179.7 . . . . ? C12C C11C C16C C15C -0.908(2) . . . . ? Cl1G C11C C16C C15C 178.7 . . . . ? C14C C15C C16C C11C 1.0 . . . . ? C4C C7C C17C C14C 180.0 . . . . ? C13C C14C C17C C7C 4.9 . . . . ? C15C C14C C17C C7C -176.0 . . . . ? O2H N1H C1D C6D -177.7 . . . . ? O1H N1H C1D C6D 5.0 . . . . ? O2H N1H C1D C2D -0.2 . . . . ? O1H N1H C1D C2D -177.5 . . . . ? C6D C1D C2D C3D -1.0 . . . . ? N1H C1D C2D C3D -178.6 . . . . ? C1D C2D C3D C4D 1.2 . . . . ? C2D C3D C4D C5D -1.3 . . . . ? C2D C3D C4D C7D 179.6 . . . . ? C3D C4D C5D C6D 1.104(2) . . . . ? C7D C4D C5D C6D -179.7 . . . . ? N1H C1D C6D C5D 178.2 . . . . ? C2D C1D C6D C5D 0.9 . . . . ? C4D C5D C6D C1D -0.9 . . . . ? C3D C4D C7D C17D -4.9 . . . . ? C5D C4D C7D C17D 175.9 . . . . ? C16D C11D C12D C13D 1.0 . . . . ? Cl1H C11D C12D C13D -178.5 . . . . ? C11D C12D C13D C14D -1.230(1) . . . . ? C12D C13D C14D C15D 1.3 . . . . ? C12D C13D C14D C17D -179.6 . . . . ? C13D C14D C15D C16D -1.1 . . . . ? C17D C14D C15D C16D 179.7 . . . . ? C12D C11D C16D C15D -0.9 . . . . ? Cl1H C11D C16D C15D 178.7 . . . . ? C14D C15D C16D C11D 1.0 . . . . ? C4D C7D C17D C14D 180.0 . . . . ? C13D C14D C17D C7D 4.9 . . . . ? C15D C14D C17D C7D -176.0 . . . . ? _diffrn_measured_fraction_theta_max 0.491 _diffrn_reflns_theta_full 27.80 _diffrn_measured_fraction_theta_full 0.491 _refine_diff_density_max 0.265 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.054 # start Validation Reply Form _vrf_ABSTM02_CNS-EtOAc-big-A1 ; PROBLEM: The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:46. ; _vrf_REFLT03_CNS-EtOAc-big-A1 ; PROBLEM: Reflection count < 85% complete (theta max?) RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. The measurement was performed in a hemisphere strategy. ; _vrf_SYMMG01_CNS-EtOAc-big-A1 ; PROBLEM: Unrecognised _symmetry_space_group_name_H-M RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. ; _vrf_SYMMG02_CNS-EtOAc-big-A1 ; PROBLEM: Supplied _symmetry_space_group_name_H-M not recognised RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. ; _vrf_PLAT029_CNS-EtOAc-big-A1 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.49 RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. The measurement was performed in a hemisphere strategy. ; _vrf_PLAT061_CNS-EtOAc-big-A1 ; PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.10 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:46. ; # end Validation Reply Form #===END data_CNS-MeCNI-small-P21/c _database_code_depnum_ccdc_archive 'CCDC 761225' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall 'P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9216(3) _cell_length_b 12.9663(10) _cell_length_c 12.2348(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.153(3) _cell_angle_gamma 90.00 _cell_volume 621.18(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3495 _cell_measurement_theta_min 3.142 _cell_measurement_theta_max 20.826 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.210189 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3475 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0755 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.79 _reflns_number_total 2540 _reflns_number_gt 998 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0949P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2540 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1832 _refine_ls_R_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.2167 _refine_ls_wR_factor_gt 0.1595 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.939 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3660(18) -0.4607(2) -0.1748(7) 0.124(3) Uani 0.50 1 d P . . N11 N 0.372(4) -0.4189(10) -0.1718(13) 0.093(3) Uani 0.50 1 d P . . O11 O 0.308(3) -0.4961(7) -0.1227(7) 0.145(4) Uani 0.50 1 d P . . O12 O 0.4945(13) -0.4130(3) -0.2573(4) 0.1185(16) Uani 0.50 1 d P . . C1 C 0.2594(6) -0.3288(2) -0.1229(2) 0.0779(8) Uani 1 1 d . . . C2 C 0.3147(6) -0.2390(2) -0.17932(19) 0.0840(8) Uani 1 1 d . . . H2A H 0.4125 -0.2405 -0.2468 0.101 Uiso 1 1 calc R . . C3 C 0.2224(6) -0.14729(19) -0.1338(2) 0.0788(7) Uani 1 1 d . . . H3A H 0.2570 -0.0862 -0.1715 0.095 Uiso 1 1 calc R . . C4 C 0.0784(5) -0.14335(18) -0.03273(19) 0.0686(7) Uani 1 1 d . . . C5 C 0.0272(6) -0.23637(18) 0.02053(19) 0.0758(7) Uani 1 1 d . . . H5A H -0.0728 -0.2356 0.0877 0.091 Uiso 1 1 calc R . . C6 C 0.1191(6) -0.32917(18) -0.0228(2) 0.0802(8) Uani 1 1 d . . . H6A H 0.0872 -0.3905 0.0147 0.096 Uiso 1 1 calc R . . C7 C -0.0236(6) -0.04676(15) 0.0183(2) 0.0764(7) Uani 1 1 d . . . H7A H -0.1333 -0.0525 0.0835 0.092 Uiso 1 1 calc R . . Cl11 Cl -0.3660(18) 0.4607(2) 0.1748(7) 0.124(3) Uani 0.50 1 d P . . N1 N -0.372(4) 0.4189(10) 0.1718(13) 0.093(3) Uani 0.50 1 d P . . O1 O -0.308(3) 0.4961(7) 0.1227(7) 0.145(4) Uani 0.50 1 d P . . O2 O -0.4945(13) 0.4130(3) 0.2573(4) 0.1185(16) Uani 0.50 1 d P . . C11 C -0.2594(6) 0.3288(2) 0.1229(2) 0.0779(8) Uani 1 1 d . . . C12 C -0.3147(6) 0.2390(2) 0.17932(19) 0.0840(8) Uani 1 1 d . . . H12A H -0.4125 0.2405 0.2468 0.101 Uiso 1 1 calc R . . C13 C -0.2224(6) 0.14729(19) 0.1338(2) 0.0788(7) Uani 1 1 d . . . H13A H -0.2570 0.0862 0.1715 0.095 Uiso 1 1 calc R . . C14 C -0.0784(5) 0.14335(18) 0.03273(19) 0.0686(7) Uani 1 1 d . . . C15 C -0.0272(6) 0.23637(18) -0.02053(19) 0.0758(7) Uani 1 1 d . . . H15A H 0.0728 0.2356 -0.0877 0.091 Uiso 1 1 calc R . . C16 C -0.1191(6) 0.32917(18) 0.0228(2) 0.0802(8) Uani 1 1 d . . . H16A H -0.0872 0.3905 -0.0147 0.096 Uiso 1 1 calc R . . C17 C 0.0236(6) 0.04676(15) -0.0183(2) 0.0764(7) Uani 1 1 d . . . H17A H 0.1333 0.0525 -0.0835 0.092 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.120(3) 0.103(5) 0.149(5) -0.056(5) 0.013(3) 0.018(3) N11 0.094(5) 0.098(8) 0.085(8) 0.012(7) -0.008(5) -0.016(7) O11 0.186(6) 0.077(4) 0.178(7) 0.003(4) 0.049(4) 0.016(4) O12 0.160(4) 0.092(3) 0.106(4) -0.028(3) 0.037(3) 0.020(3) C1 0.0693(17) 0.0805(19) 0.084(2) -0.0182(15) 0.0027(13) 0.0067(13) C2 0.0759(17) 0.103(2) 0.0741(18) -0.0030(15) 0.0138(14) -0.0027(14) C3 0.0790(16) 0.0820(17) 0.0763(18) 0.0041(14) 0.0115(13) -0.0024(13) C4 0.0605(14) 0.0758(15) 0.0699(16) -0.0040(13) 0.0058(11) -0.0012(11) C5 0.0791(16) 0.0788(16) 0.0707(16) 0.0044(14) 0.0143(12) 0.0000(13) C6 0.0819(17) 0.0730(17) 0.086(2) 0.0023(14) 0.0103(14) 0.0034(13) C7 0.0714(15) 0.0772(15) 0.0809(17) 0.0033(13) 0.0070(12) -0.0019(13) Cl11 0.120(3) 0.103(5) 0.149(5) -0.056(5) 0.013(3) 0.018(3) N1 0.094(5) 0.098(8) 0.085(8) 0.012(7) -0.008(5) -0.016(7) O1 0.186(6) 0.077(4) 0.178(7) 0.003(4) 0.049(4) 0.016(4) O2 0.160(4) 0.092(3) 0.106(4) -0.028(3) 0.037(3) 0.020(3) C11 0.0693(17) 0.0805(19) 0.084(2) -0.0182(15) 0.0027(13) 0.0067(13) C12 0.0759(17) 0.103(2) 0.0741(18) -0.0030(15) 0.0138(14) -0.0027(14) C13 0.0790(16) 0.0820(17) 0.0763(18) 0.0041(14) 0.0115(13) -0.0024(13) C14 0.0605(14) 0.0758(15) 0.0699(16) -0.0040(13) 0.0058(11) -0.0012(11) C15 0.0791(16) 0.0788(16) 0.0707(16) 0.0044(14) 0.0143(12) 0.0000(13) C16 0.0819(17) 0.0730(17) 0.086(2) 0.0023(14) 0.0103(14) 0.0034(13) C17 0.0714(15) 0.0772(15) 0.0809(17) 0.0033(13) 0.0070(12) -0.0019(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.543(13) . ? Cl1 O11 0.827(8) . ? Cl1 O12 1.308(8) . ? Cl1 C1 1.879(4) . ? N11 O12 1.178(18) . ? N11 O11 1.20(2) . ? N11 C1 1.395(11) . ? C1 C6 1.370(3) . ? C1 C2 1.378(3) . ? C2 C3 1.370(3) . ? C2 H2A 0.9300 . ? C3 C4 1.388(3) . ? C3 H3A 0.9300 . ? C4 C5 1.391(3) . ? C4 C7 1.465(3) . ? C5 C6 1.371(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.309(4) . ? C7 H7A 0.9300 . ? Cl11 N1 0.543(13) . ? Cl11 O1 0.827(8) . ? Cl11 O2 1.308(8) . ? Cl11 C11 1.879(4) . ? N1 O2 1.178(18) . ? N1 O1 1.20(2) . ? N1 C11 1.395(11) . ? C11 C16 1.370(3) . ? C11 C12 1.378(3) . ? C12 C13 1.370(3) . ? C12 H12A 0.9300 . ? C13 C14 1.388(3) . ? C13 H13A 0.9300 . ? C14 C15 1.391(3) . ? C14 C17 1.465(3) . ? C15 C16 1.371(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 121(3) . . ? N11 Cl1 O12 64(2) . . ? O11 Cl1 O12 172.1(10) . . ? N11 Cl1 C1 23(2) . . ? O11 Cl1 C1 99.7(10) . . ? O12 Cl1 C1 86.2(3) . . ? Cl1 N11 O12 91(2) . . ? Cl1 N11 O11 36(2) . . ? O12 N11 O11 127.2(11) . . ? Cl1 N11 C1 148(3) . . ? O12 N11 C1 118.7(12) . . ? O11 N11 C1 113.9(12) . . ? Cl1 O11 N11 22.9(10) . . ? N11 O12 Cl1 24.5(6) . . ? C6 C1 C2 122.2(3) . . ? C6 C1 N11 122.2(8) . . ? C2 C1 N11 115.6(8) . . ? C6 C1 Cl1 114.0(3) . . ? C2 C1 Cl1 123.8(3) . . ? N11 C1 Cl1 8.7(9) . . ? C3 C2 C1 118.5(2) . . ? C3 C2 H2A 120.7 . . ? C1 C2 H2A 120.7 . . ? C2 C3 C4 121.6(3) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 117.5(2) . . ? C3 C4 C7 123.0(3) . . ? C5 C4 C7 119.5(2) . . ? C6 C5 C4 122.2(2) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C5 C6 C1 118.0(2) . . ? C5 C6 H6A 121.0 . . ? C1 C6 H6A 121.0 . . ? C17 C7 C4 126.8(3) . . ? C17 C7 H7A 116.6 . . ? C4 C7 H7A 116.6 . . ? N1 Cl11 O1 121(3) . . ? N1 Cl11 O2 64(2) . . ? O1 Cl11 O2 172.1(10) . . ? N1 Cl11 C11 23(2) . . ? O1 Cl11 C11 99.7(10) . . ? O2 Cl11 C11 86.2(3) . . ? Cl11 N1 O2 91(2) . . ? Cl11 N1 O1 36(2) . . ? O2 N1 O1 127.2(11) . . ? Cl11 N1 C11 148(3) . . ? O2 N1 C11 118.7(12) . . ? O1 N1 C11 113.9(12) . . ? Cl11 O1 N1 22.9(10) . . ? N1 O2 Cl11 24.5(6) . . ? C16 C11 C12 122.2(3) . . ? C16 C11 N1 122.2(8) . . ? C12 C11 N1 115.6(8) . . ? C16 C11 Cl11 114.0(3) . . ? C12 C11 Cl11 123.8(3) . . ? N1 C11 Cl11 8.7(9) . . ? C13 C12 C11 118.5(2) . . ? C13 C12 H12A 120.7 . . ? C11 C12 H12A 120.7 . . ? C12 C13 C14 121.6(3) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C13 C14 C15 117.5(2) . . ? C13 C14 C17 123.0(3) . . ? C15 C14 C17 119.5(2) . . ? C16 C15 C14 122.2(2) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C15 C16 C11 118.0(2) . . ? C15 C16 H16A 121.0 . . ? C11 C16 H16A 121.0 . . ? C7 C17 C14 126.8(3) . . ? C7 C17 H17A 116.6 . . ? C14 C17 H17A 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 173.1(16) . . . . ? C1 Cl1 N11 O12 -162(6) . . . . ? O12 Cl1 N11 O11 -173.1(16) . . . . ? C1 Cl1 N11 O11 25(7) . . . . ? O11 Cl1 N11 C1 -25(7) . . . . ? O12 Cl1 N11 C1 162(6) . . . . ? O12 Cl1 O11 N11 128(11) . . . . ? C1 Cl1 O11 N11 -10(3) . . . . ? O12 N11 O11 Cl1 -9(2) . . . . ? C1 N11 O11 Cl1 166(4) . . . . ? O11 N11 O12 Cl1 5.1(12) . . . . ? C1 N11 O12 Cl1 -169(3) . . . . ? O11 Cl1 O12 N11 -131(10) . . . . ? C1 Cl1 O12 N11 7(2) . . . . ? Cl1 N11 C1 C6 22(6) . . . . ? O12 N11 C1 C6 -178.9(9) . . . . ? O11 N11 C1 C6 5.8(17) . . . . ? Cl1 N11 C1 C2 -162(5) . . . . ? O12 N11 C1 C2 -2.1(15) . . . . ? O11 N11 C1 C2 -177.3(10) . . . . ? O12 N11 C1 Cl1 159(7) . . . . ? O11 N11 C1 Cl1 -16(5) . . . . ? N11 Cl1 C1 C6 -160(6) . . . . ? O11 Cl1 C1 C6 -1.5(11) . . . . ? O12 Cl1 C1 C6 -176.2(4) . . . . ? N11 Cl1 C1 C2 20(6) . . . . ? O11 Cl1 C1 C2 178.6(9) . . . . ? O12 Cl1 C1 C2 4.0(6) . . . . ? O11 Cl1 C1 N11 159(6) . . . . ? O12 Cl1 C1 N11 -16(5) . . . . ? C6 C1 C2 C3 -0.7(4) . . . . ? N11 C1 C2 C3 -177.5(7) . . . . ? Cl1 C1 C2 C3 179.2(3) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C2 C3 C4 C7 -179.9(2) . . . . ? C3 C4 C5 C6 1.2(3) . . . . ? C7 C4 C5 C6 -179.6(2) . . . . ? C4 C5 C6 C1 -1.3(3) . . . . ? C2 C1 C6 C5 1.1(4) . . . . ? N11 C1 C6 C5 177.7(8) . . . . ? Cl1 C1 C6 C5 -178.8(3) . . . . ? C3 C4 C7 C17 -4.7(4) . . . . ? C5 C4 C7 C17 176.1(3) . . . . ? O1 Cl11 N1 O2 -173.1(16) . . . . ? C11 Cl11 N1 O2 162(6) . . . . ? O2 Cl11 N1 O1 173.1(16) . . . . ? C11 Cl11 N1 O1 -25(7) . . . . ? O1 Cl11 N1 C11 25(7) . . . . ? O2 Cl11 N1 C11 -162(6) . . . . ? O2 Cl11 O1 N1 -128(11) . . . . ? C11 Cl11 O1 N1 10(3) . . . . ? O2 N1 O1 Cl11 9(2) . . . . ? C11 N1 O1 Cl11 -166(4) . . . . ? O1 N1 O2 Cl11 -5.1(12) . . . . ? C11 N1 O2 Cl11 169(3) . . . . ? O1 Cl11 O2 N1 131(10) . . . . ? C11 Cl11 O2 N1 -7(2) . . . . ? Cl11 N1 C11 C16 -22(6) . . . . ? O2 N1 C11 C16 178.9(9) . . . . ? O1 N1 C11 C16 -5.8(17) . . . . ? Cl11 N1 C11 C12 162(5) . . . . ? O2 N1 C11 C12 2.1(15) . . . . ? O1 N1 C11 C12 177.3(10) . . . . ? O2 N1 C11 Cl11 -159(7) . . . . ? O1 N1 C11 Cl11 16(5) . . . . ? N1 Cl11 C11 C16 160(6) . . . . ? O1 Cl11 C11 C16 1.5(11) . . . . ? O2 Cl11 C11 C16 176.2(4) . . . . ? N1 Cl11 C11 C12 -20(6) . . . . ? O1 Cl11 C11 C12 -178.6(9) . . . . ? O2 Cl11 C11 C12 -4.0(6) . . . . ? O1 Cl11 C11 N1 -159(6) . . . . ? O2 Cl11 C11 N1 16(5) . . . . ? C16 C11 C12 C13 0.7(4) . . . . ? N1 C11 C12 C13 177.5(7) . . . . ? Cl11 C11 C12 C13 -179.2(3) . . . . ? C11 C12 C13 C14 -0.5(4) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ? C12 C13 C14 C17 179.9(2) . . . . ? C13 C14 C15 C16 -1.2(3) . . . . ? C17 C14 C15 C16 179.6(2) . . . . ? C14 C15 C16 C11 1.3(3) . . . . ? C12 C11 C16 C15 -1.1(4) . . . . ? N1 C11 C16 C15 -177.7(8) . . . . ? Cl11 C11 C16 C15 178.8(3) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 4.7(4) . . . . ? C15 C14 C17 C7 -176.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.879 _diffrn_reflns_theta_full 27.79 _diffrn_measured_fraction_theta_full 0.879 _refine_diff_density_max 0.188 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.044 # start Validation Reply Form _vrf_ABSTM02_CNS-MeCNI-small-P21_c ; PROBLEM: The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; _vrf_SYMMG02_CNS-MeCNI-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-MeCNI-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.88 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; _vrf_PLAT061_CNS-MeCNI-small-P21_c ; PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.22 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; # end Validation Reply Form #===END data_CNS-MeCNI-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761226' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9216(3) _cell_length_b 12.9663(10) _cell_length_c 12.2348(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.153(3) _cell_angle_gamma 90.00 _cell_volume 621.18(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3495 _cell_measurement_theta_min 3.142 _cell_measurement_theta_max 20.826 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.210189 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3475 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0755 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.79 _reflns_number_total 2540 _reflns_number_gt 998 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0949P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 2540 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1831 _refine_ls_R_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.2167 _refine_ls_wR_factor_gt 0.1595 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.939 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3660(18) -0.4607(2) -0.1748(7) 0.124(3) Uani 0.489(15) 1 d P . . N11 N 0.372(4) -0.4189(9) -0.1718(13) 0.093(3) Uani 0.511(15) 1 d P . . O11 O 0.308(3) -0.4961(7) -0.1227(7) 0.145(4) Uani 0.511(15) 1 d P . . O12 O 0.4945(13) -0.4130(3) -0.2573(4) 0.1185(16) Uani 0.511(15) 1 d P . . C1 C 0.2595(6) -0.3288(2) -0.1229(2) 0.0779(8) Uani 1 1 d . . . C2 C 0.3147(6) -0.2390(2) -0.17933(19) 0.0840(8) Uani 1 1 d . . . H2A H 0.4125 -0.2405 -0.2469 0.101 Uiso 1 1 calc R . . C3 C 0.2224(6) -0.1473(2) -0.1338(2) 0.0789(7) Uani 1 1 d . . . H3A H 0.2569 -0.0862 -0.1715 0.095 Uiso 1 1 calc R . . C4 C 0.0784(5) -0.14335(18) -0.03274(19) 0.0686(7) Uani 1 1 d . . . C5 C 0.0272(6) -0.23637(18) 0.02053(19) 0.0759(7) Uani 1 1 d . . . H5A H -0.0728 -0.2356 0.0877 0.091 Uiso 1 1 calc R . . C6 C 0.1191(6) -0.32917(18) -0.0228(2) 0.0802(8) Uani 1 1 d . . . H6A H 0.0872 -0.3905 0.0147 0.096 Uiso 1 1 calc R . . C7 C -0.0236(6) -0.04676(15) 0.0183(2) 0.0764(7) Uani 1 1 d . . . H7A H -0.1333 -0.0525 0.0835 0.092 Uiso 1 1 calc R . . Cl11 Cl -0.3660(18) 0.4607(2) 0.1748(7) 0.124(3) Uani 0.511(15) 1 d P . . N1 N -0.372(4) 0.4189(9) 0.1718(13) 0.093(3) Uani 0.489(15) 1 d P . . O1 O -0.308(3) 0.4961(7) 0.1227(7) 0.145(4) Uani 0.489(15) 1 d P . . O2 O -0.4945(13) 0.4130(3) 0.2573(4) 0.1185(16) Uani 0.489(15) 1 d P . . C11 C -0.2595(6) 0.3288(2) 0.1229(2) 0.0779(8) Uani 1 1 d . . . C12 C -0.3147(6) 0.2390(2) 0.17933(19) 0.0840(8) Uani 1 1 d . . . H12A H -0.4125 0.2405 0.2469 0.101 Uiso 1 1 calc R . . C13 C -0.2224(6) 0.1473(2) 0.1338(2) 0.0789(7) Uani 1 1 d . . . H13A H -0.2569 0.0862 0.1715 0.095 Uiso 1 1 calc R . . C14 C -0.0784(5) 0.14335(18) 0.03274(19) 0.0686(7) Uani 1 1 d . . . C15 C -0.0272(6) 0.23637(18) -0.02053(19) 0.0759(7) Uani 1 1 d . . . H15A H 0.0728 0.2356 -0.0877 0.091 Uiso 1 1 calc R . . C16 C -0.1191(6) 0.32917(18) 0.0228(2) 0.0802(8) Uani 1 1 d . . . H16A H -0.0872 0.3905 -0.0147 0.096 Uiso 1 1 calc R . . C17 C 0.0236(6) 0.04676(15) -0.0183(2) 0.0764(7) Uani 1 1 d . . . H17A H 0.1333 0.0525 -0.0835 0.092 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.120(3) 0.102(5) 0.149(5) -0.056(5) 0.013(3) 0.018(3) N11 0.094(5) 0.098(8) 0.085(8) 0.012(7) -0.008(5) -0.016(7) O11 0.186(6) 0.077(4) 0.178(7) 0.003(4) 0.049(4) 0.016(4) O12 0.160(4) 0.092(3) 0.106(4) -0.028(3) 0.037(3) 0.020(3) C1 0.0693(17) 0.0805(19) 0.084(2) -0.0182(15) 0.0027(13) 0.0067(13) C2 0.0759(17) 0.103(2) 0.0741(18) -0.0030(15) 0.0138(14) -0.0027(14) C3 0.0790(16) 0.0820(17) 0.0763(18) 0.0041(14) 0.0115(13) -0.0024(13) C4 0.0605(14) 0.0758(15) 0.0698(17) -0.0040(13) 0.0058(11) -0.0012(11) C5 0.0791(16) 0.0789(16) 0.0707(16) 0.0044(14) 0.0143(12) 0.0000(13) C6 0.0819(17) 0.0730(17) 0.086(2) 0.0023(14) 0.0104(14) 0.0034(13) C7 0.0714(15) 0.0771(15) 0.0809(17) 0.0033(13) 0.0070(12) -0.0019(13) Cl11 0.120(3) 0.102(5) 0.149(5) -0.056(5) 0.013(3) 0.018(3) N1 0.094(5) 0.098(8) 0.085(8) 0.012(7) -0.008(5) -0.016(7) O1 0.186(6) 0.077(4) 0.178(7) 0.003(4) 0.049(4) 0.016(4) O2 0.160(4) 0.092(3) 0.106(4) -0.028(3) 0.037(3) 0.020(3) C11 0.0693(17) 0.0805(19) 0.084(2) -0.0182(15) 0.0027(13) 0.0067(13) C12 0.0759(17) 0.103(2) 0.0741(18) -0.0030(15) 0.0138(14) -0.0027(14) C13 0.0790(16) 0.0820(17) 0.0763(18) 0.0041(14) 0.0115(13) -0.0024(13) C14 0.0605(14) 0.0758(15) 0.0698(17) -0.0040(13) 0.0058(11) -0.0012(11) C15 0.0791(16) 0.0789(16) 0.0707(16) 0.0044(14) 0.0143(12) 0.0000(13) C16 0.0819(17) 0.0730(17) 0.086(2) 0.0023(14) 0.0104(14) 0.0034(13) C17 0.0714(15) 0.0771(15) 0.0809(17) 0.0033(13) 0.0070(12) -0.0019(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.544(13) . ? Cl1 O11 0.827(8) . ? Cl1 O12 1.308(8) . ? Cl1 C1 1.879(4) . ? N11 O12 1.178(18) . ? N11 O11 1.20(2) . ? N11 C1 1.395(11) . ? C1 C6 1.370(3) . ? C1 C2 1.378(3) . ? C2 C3 1.370(3) . ? C2 H2A 0.9300 . ? C3 C4 1.388(3) . ? C3 H3A 0.9300 . ? C4 C5 1.391(3) . ? C4 C7 1.465(3) . ? C5 C6 1.371(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.309(4) . ? C7 H7A 0.9300 . ? Cl11 N1 0.544(13) . ? Cl11 O1 0.827(8) . ? Cl11 O2 1.308(8) . ? Cl11 C11 1.879(4) . ? N1 O2 1.178(18) . ? N1 O1 1.20(2) . ? N1 C11 1.395(11) . ? C11 C16 1.370(3) . ? C11 C12 1.378(3) . ? C12 C13 1.370(3) . ? C12 H12A 0.9300 . ? C13 C14 1.388(3) . ? C13 H13A 0.9300 . ? C14 C15 1.391(3) . ? C14 C17 1.465(3) . ? C15 C16 1.371(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 121(3) . . ? N11 Cl1 O12 64(2) . . ? O11 Cl1 O12 172.1(10) . . ? N11 Cl1 C1 23(2) . . ? O11 Cl1 C1 99.8(10) . . ? O12 Cl1 C1 86.2(3) . . ? Cl1 N11 O12 91(2) . . ? Cl1 N11 O11 36(2) . . ? O12 N11 O11 127.2(11) . . ? Cl1 N11 C1 148(3) . . ? O12 N11 C1 118.8(12) . . ? O11 N11 C1 113.9(12) . . ? Cl1 O11 N11 22.9(10) . . ? N11 O12 Cl1 24.5(6) . . ? C6 C1 C2 122.2(3) . . ? C6 C1 N11 122.2(8) . . ? C2 C1 N11 115.5(8) . . ? C6 C1 Cl1 114.0(3) . . ? C2 C1 Cl1 123.8(3) . . ? N11 C1 Cl1 8.7(9) . . ? C3 C2 C1 118.5(2) . . ? C3 C2 H2A 120.7 . . ? C1 C2 H2A 120.7 . . ? C2 C3 C4 121.6(3) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 117.5(2) . . ? C3 C4 C7 123.0(3) . . ? C5 C4 C7 119.5(2) . . ? C6 C5 C4 122.2(2) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C5 C6 C1 118.0(2) . . ? C5 C6 H6A 121.0 . . ? C1 C6 H6A 121.0 . . ? C17 C7 C4 126.8(3) . . ? C17 C7 H7A 116.6 . . ? C4 C7 H7A 116.6 . . ? N1 Cl11 O1 121(3) . . ? N1 Cl11 O2 64(2) . . ? O1 Cl11 O2 172.1(10) . . ? N1 Cl11 C11 23(2) . . ? O1 Cl11 C11 99.8(10) . . ? O2 Cl11 C11 86.2(3) . . ? Cl11 N1 O2 91(2) . . ? Cl11 N1 O1 36(2) . . ? O2 N1 O1 127.2(11) . . ? Cl11 N1 C11 148(3) . . ? O2 N1 C11 118.8(12) . . ? O1 N1 C11 113.9(12) . . ? Cl11 O1 N1 22.9(10) . . ? N1 O2 Cl11 24.5(6) . . ? C16 C11 C12 122.2(3) . . ? C16 C11 N1 122.2(8) . . ? C12 C11 N1 115.5(8) . . ? C16 C11 Cl11 114.0(3) . . ? C12 C11 Cl11 123.8(3) . . ? N1 C11 Cl11 8.7(9) . . ? C13 C12 C11 118.5(2) . . ? C13 C12 H12A 120.7 . . ? C11 C12 H12A 120.7 . . ? C12 C13 C14 121.6(3) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C13 C14 C15 117.5(2) . . ? C13 C14 C17 123.0(3) . . ? C15 C14 C17 119.5(2) . . ? C16 C15 C14 122.2(2) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C15 C16 C11 118.0(2) . . ? C15 C16 H16A 121.0 . . ? C11 C16 H16A 121.0 . . ? C7 C17 C14 126.8(3) . . ? C7 C17 H17A 116.6 . . ? C14 C17 H17A 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 173.1(16) . . . . ? C1 Cl1 N11 O12 -162(6) . . . . ? O12 Cl1 N11 O11 -173.1(16) . . . . ? C1 Cl1 N11 O11 25(7) . . . . ? O11 Cl1 N11 C1 -25(7) . . . . ? O12 Cl1 N11 C1 162(6) . . . . ? O12 Cl1 O11 N11 128(11) . . . . ? C1 Cl1 O11 N11 -10(3) . . . . ? O12 N11 O11 Cl1 -9(2) . . . . ? C1 N11 O11 Cl1 166(4) . . . . ? O11 N11 O12 Cl1 5.1(12) . . . . ? C1 N11 O12 Cl1 -169(3) . . . . ? O11 Cl1 O12 N11 -132(10) . . . . ? C1 Cl1 O12 N11 7(2) . . . . ? Cl1 N11 C1 C6 22(6) . . . . ? O12 N11 C1 C6 -178.9(9) . . . . ? O11 N11 C1 C6 5.9(17) . . . . ? Cl1 N11 C1 C2 -162(5) . . . . ? O12 N11 C1 C2 -2.1(15) . . . . ? O11 N11 C1 C2 -177.3(10) . . . . ? O12 N11 C1 Cl1 160(7) . . . . ? O11 N11 C1 Cl1 -16(5) . . . . ? N11 Cl1 C1 C6 -160(5) . . . . ? O11 Cl1 C1 C6 -1.5(11) . . . . ? O12 Cl1 C1 C6 -176.2(4) . . . . ? N11 Cl1 C1 C2 20(6) . . . . ? O11 Cl1 C1 C2 178.7(9) . . . . ? O12 Cl1 C1 C2 4.0(6) . . . . ? O11 Cl1 C1 N11 159(6) . . . . ? O12 Cl1 C1 N11 -16(5) . . . . ? C6 C1 C2 C3 -0.7(4) . . . . ? N11 C1 C2 C3 -177.5(7) . . . . ? Cl1 C1 C2 C3 179.2(3) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C2 C3 C4 C7 -179.9(2) . . . . ? C3 C4 C5 C6 1.2(3) . . . . ? C7 C4 C5 C6 -179.6(2) . . . . ? C4 C5 C6 C1 -1.3(3) . . . . ? C2 C1 C6 C5 1.1(4) . . . . ? N11 C1 C6 C5 177.7(7) . . . . ? Cl1 C1 C6 C5 -178.8(3) . . . . ? C3 C4 C7 C17 -4.7(4) . . . . ? C5 C4 C7 C17 176.1(3) . . . . ? O1 Cl11 N1 O2 -173.1(16) . . . . ? C11 Cl11 N1 O2 162(6) . . . . ? O2 Cl11 N1 O1 173.1(16) . . . . ? C11 Cl11 N1 O1 -25(7) . . . . ? O1 Cl11 N1 C11 25(7) . . . . ? O2 Cl11 N1 C11 -162(6) . . . . ? O2 Cl11 O1 N1 -128(11) . . . . ? C11 Cl11 O1 N1 10(3) . . . . ? O2 N1 O1 Cl11 9(2) . . . . ? C11 N1 O1 Cl11 -166(4) . . . . ? O1 N1 O2 Cl11 -5.1(12) . . . . ? C11 N1 O2 Cl11 169(3) . . . . ? O1 Cl11 O2 N1 132(10) . . . . ? C11 Cl11 O2 N1 -7(2) . . . . ? Cl11 N1 C11 C16 -22(6) . . . . ? O2 N1 C11 C16 178.9(9) . . . . ? O1 N1 C11 C16 -5.9(17) . . . . ? Cl11 N1 C11 C12 162(5) . . . . ? O2 N1 C11 C12 2.1(15) . . . . ? O1 N1 C11 C12 177.3(10) . . . . ? O2 N1 C11 Cl11 -160(7) . . . . ? O1 N1 C11 Cl11 16(5) . . . . ? N1 Cl11 C11 C16 160(5) . . . . ? O1 Cl11 C11 C16 1.5(11) . . . . ? O2 Cl11 C11 C16 176.2(4) . . . . ? N1 Cl11 C11 C12 -20(6) . . . . ? O1 Cl11 C11 C12 -178.7(9) . . . . ? O2 Cl11 C11 C12 -4.0(6) . . . . ? O1 Cl11 C11 N1 -159(6) . . . . ? O2 Cl11 C11 N1 16(5) . . . . ? C16 C11 C12 C13 0.7(4) . . . . ? N1 C11 C12 C13 177.5(7) . . . . ? Cl11 C11 C12 C13 -179.2(3) . . . . ? C11 C12 C13 C14 -0.5(4) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ? C12 C13 C14 C17 179.9(2) . . . . ? C13 C14 C15 C16 -1.2(3) . . . . ? C17 C14 C15 C16 179.6(2) . . . . ? C14 C15 C16 C11 1.3(3) . . . . ? C12 C11 C16 C15 -1.1(4) . . . . ? N1 C11 C16 C15 -177.7(7) . . . . ? Cl11 C11 C16 C15 178.8(3) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 4.7(4) . . . . ? C15 C14 C17 C7 -176.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 27.79 _diffrn_measured_fraction_theta_full 0.916 _refine_diff_density_max 0.189 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.044 # start Validation Reply Form _vrf_ABSTM02_CNS-MeCNI-small-P21 ; PROBLEM: The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; _vrf_SYMMG02_CNS-MeCNI-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-MeCNI-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.92 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; _vrf_PLAT061_CNS-MeCNI-small-P21 ; PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.22 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; # end Validation Reply Form #===END data_CNS-MeCNII-small-P21/c _database_code_depnum_ccdc_archive 'CCDC 761227' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall 'P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9221(4) _cell_length_b 12.9733(12) _cell_length_c 12.2509(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.149(3) _cell_angle_gamma 90.00 _cell_volume 622.42(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3496 _cell_measurement_theta_min 3.140 _cell_measurement_theta_max 19.487 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.079036 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3478 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.81 _reflns_number_total 2315 _reflns_number_gt 900 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 2315 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1610 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3703(13) -0.46107(13) -0.1746(5) 0.1140(19) Uani 0.50 1 d P . . N11 N 0.365(3) -0.4160(6) -0.1745(12) 0.080(2) Uani 0.50 1 d P . . O11 O 0.3165(19) -0.4977(5) -0.1234(5) 0.131(3) Uani 0.50 1 d P . . O12 O 0.5006(9) -0.4124(3) -0.2572(3) 0.1156(13) Uani 0.50 1 d P . . C1 C 0.2612(5) -0.32924(17) -0.12288(19) 0.0738(6) Uani 1 1 d . . . C2 C 0.3139(5) -0.23872(19) -0.17898(15) 0.0821(6) Uani 1 1 d . . . H2A H 0.4104 -0.2400 -0.2466 0.099 Uiso 1 1 calc R . . C3 C 0.2224(5) -0.14746(15) -0.13380(17) 0.0759(6) Uani 1 1 d . . . H3A H 0.2574 -0.0865 -0.1715 0.091 Uiso 1 1 calc R . . C4 C 0.0787(4) -0.14344(15) -0.03309(15) 0.0658(5) Uani 1 1 d . . . C5 C 0.0279(4) -0.23597(15) 0.02047(15) 0.0724(6) Uani 1 1 d . . . H5A H -0.0706 -0.2350 0.0878 0.087 Uiso 1 1 calc R . . C6 C 0.1188(5) -0.32915(14) -0.02297(17) 0.0782(6) Uani 1 1 d . . . H6A H 0.0848 -0.3904 0.0143 0.094 Uiso 1 1 calc R . . C7 C -0.0232(5) -0.04662(11) 0.01805(16) 0.0738(6) Uani 1 1 d . . . H7A H -0.1326 -0.0524 0.0832 0.089 Uiso 1 1 calc R . . Cl11 Cl -0.3703(13) 0.46107(13) 0.1746(5) 0.1140(19) Uani 0.50 1 d P . . N1 N -0.365(3) 0.4160(6) 0.1745(12) 0.080(2) Uani 0.50 1 d P . . O1 O -0.3165(19) 0.4977(5) 0.1234(5) 0.131(3) Uani 0.50 1 d P . . O2 O -0.5006(9) 0.4124(3) 0.2572(3) 0.1156(13) Uani 0.50 1 d P . . C11 C -0.2612(5) 0.32924(17) 0.12288(19) 0.0738(6) Uani 1 1 d . . . C12 C -0.3139(5) 0.23872(19) 0.17898(15) 0.0821(6) Uani 1 1 d . . . H12A H -0.4104 0.2400 0.2466 0.099 Uiso 1 1 calc R . . C13 C -0.2224(5) 0.14746(15) 0.13380(17) 0.0759(6) Uani 1 1 d . . . H13A H -0.2574 0.0865 0.1715 0.091 Uiso 1 1 calc R . . C14 C -0.0787(4) 0.14344(15) 0.03309(15) 0.0658(5) Uani 1 1 d . . . C15 C -0.0279(4) 0.23597(15) -0.02047(15) 0.0724(6) Uani 1 1 d . . . H15A H 0.0706 0.2350 -0.0878 0.087 Uiso 1 1 calc R . . C16 C -0.1188(5) 0.32915(14) 0.02297(17) 0.0782(6) Uani 1 1 d . . . H16A H -0.0848 0.3904 -0.0143 0.094 Uiso 1 1 calc R . . C17 C 0.0232(5) 0.04662(11) -0.01805(16) 0.0738(6) Uani 1 1 d . . . H17A H 0.1326 0.0524 -0.0832 0.089 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1191(17) 0.085(4) 0.137(3) -0.040(4) 0.002(2) 0.023(3) N11 0.072(3) 0.059(5) 0.106(6) 0.008(6) -0.003(3) 0.006(5) O11 0.164(4) 0.072(3) 0.160(6) 0.013(3) 0.037(3) 0.011(3) O12 0.156(3) 0.093(2) 0.101(3) -0.020(2) 0.035(2) 0.016(2) C1 0.0580(14) 0.0868(17) 0.0760(16) -0.0153(13) -0.0009(11) 0.0068(12) C2 0.0685(14) 0.1123(17) 0.0660(14) -0.0020(13) 0.0073(11) -0.0017(13) C3 0.0703(14) 0.0798(14) 0.0781(16) 0.0050(12) 0.0088(11) -0.0014(11) C4 0.0524(12) 0.0798(13) 0.0648(14) -0.0040(12) 0.0008(10) 0.0004(10) C5 0.0697(13) 0.0840(14) 0.0642(13) 0.0033(12) 0.0090(10) -0.0002(12) C6 0.0746(15) 0.0768(15) 0.0834(17) 0.0020(12) 0.0046(12) 0.0022(11) C7 0.0623(12) 0.0833(14) 0.0757(14) 0.0074(12) 0.0051(10) -0.0064(12) Cl11 0.1191(17) 0.085(4) 0.137(3) -0.040(4) 0.002(2) 0.023(3) N1 0.072(3) 0.059(5) 0.106(6) 0.008(6) -0.003(3) 0.006(5) O1 0.164(4) 0.072(3) 0.160(6) 0.013(3) 0.037(3) 0.011(3) O2 0.156(3) 0.093(2) 0.101(3) -0.020(2) 0.035(2) 0.016(2) C11 0.0580(14) 0.0868(17) 0.0760(16) -0.0153(13) -0.0009(11) 0.0068(12) C12 0.0685(14) 0.1123(17) 0.0660(14) -0.0020(13) 0.0073(11) -0.0017(13) C13 0.0703(14) 0.0798(14) 0.0781(16) 0.0050(12) 0.0088(11) -0.0014(11) C14 0.0524(12) 0.0798(13) 0.0648(14) -0.0040(12) 0.0008(10) 0.0004(10) C15 0.0697(13) 0.0840(14) 0.0642(13) 0.0033(12) 0.0090(10) -0.0002(12) C16 0.0746(15) 0.0768(15) 0.0834(17) 0.0020(12) 0.0046(12) 0.0022(11) C17 0.0623(12) 0.0833(14) 0.0757(14) 0.0074(12) 0.0051(10) -0.0064(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.585(8) . ? Cl1 O11 0.824(6) . ? Cl1 O12 1.319(6) . ? Cl1 C1 1.881(3) . ? N11 O12 1.171(14) . ? N11 O11 1.251(16) . ? N11 C1 1.364(8) . ? C1 C6 1.373(2) . ? C1 C2 1.382(2) . ? C2 C3 1.363(2) . ? C2 H2A 0.9300 . ? C3 C4 1.385(2) . ? C3 H3A 0.9300 . ? C4 C5 1.388(2) . ? C4 C7 1.469(2) . ? C5 C6 1.376(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.304(3) . ? C7 H7A 0.9300 . ? Cl11 N1 0.585(8) . ? Cl11 O1 0.824(6) . ? Cl11 O2 1.319(6) . ? Cl11 C11 1.881(3) . ? N1 O2 1.171(14) . ? N1 O1 1.251(16) . ? N1 C11 1.364(8) . ? C11 C16 1.373(2) . ? C11 C12 1.382(2) . ? C12 C13 1.363(2) . ? C12 H12A 0.9300 . ? C13 C14 1.385(2) . ? C13 H13A 0.9300 . ? C14 C15 1.388(2) . ? C14 C17 1.469(2) . ? C15 C16 1.376(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 124(2) . . ? N11 Cl1 O12 62.6(18) . . ? O11 Cl1 O12 170.5(8) . . ? N11 Cl1 C1 23.3(17) . . ? O11 Cl1 C1 101.3(8) . . ? O12 Cl1 C1 85.9(2) . . ? Cl1 N11 O12 91.1(18) . . ? Cl1 N11 O11 32.9(16) . . ? O12 N11 O11 123.7(7) . . ? Cl1 N11 C1 147(2) . . ? O12 N11 C1 122.0(9) . . ? O11 N11 C1 114.2(10) . . ? Cl1 O11 N11 22.7(8) . . ? N11 O12 Cl1 26.3(4) . . ? N11 C1 C6 124.1(6) . . ? N11 C1 C2 114.5(6) . . ? C6 C1 C2 121.5(2) . . ? N11 C1 Cl1 9.8(7) . . ? C6 C1 Cl1 114.3(3) . . ? C2 C1 Cl1 124.2(3) . . ? C3 C2 C1 119.09(19) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 121.6(2) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 117.68(19) . . ? C3 C4 C7 123.1(2) . . ? C5 C4 C7 119.25(18) . . ? C6 C5 C4 122.02(18) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C1 C6 C5 118.2(2) . . ? C1 C6 H6A 120.9 . . ? C5 C6 H6A 120.9 . . ? C17 C7 C4 127.0(3) . . ? C17 C7 H7A 116.5 . . ? C4 C7 H7A 116.5 . . ? N1 Cl11 O1 124(2) . . ? N1 Cl11 O2 62.6(18) . . ? O1 Cl11 O2 170.5(8) . . ? N1 Cl11 C11 23.3(17) . . ? O1 Cl11 C11 101.3(8) . . ? O2 Cl11 C11 85.9(2) . . ? Cl11 N1 O2 91.1(18) . . ? Cl11 N1 O1 32.9(16) . . ? O2 N1 O1 123.7(7) . . ? Cl11 N1 C11 147(2) . . ? O2 N1 C11 122.0(9) . . ? O1 N1 C11 114.2(10) . . ? Cl11 O1 N1 22.7(8) . . ? N1 O2 Cl11 26.3(4) . . ? N1 C11 C16 124.1(6) . . ? N1 C11 C12 114.5(6) . . ? C16 C11 C12 121.5(2) . . ? N1 C11 Cl11 9.8(7) . . ? C16 C11 Cl11 114.3(3) . . ? C12 C11 Cl11 124.2(3) . . ? C13 C12 C11 119.09(19) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C14 121.6(2) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C13 C14 C15 117.68(19) . . ? C13 C14 C17 123.1(2) . . ? C15 C14 C17 119.25(18) . . ? C16 C15 C14 122.02(18) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C11 C16 C15 118.2(2) . . ? C11 C16 H16A 120.9 . . ? C15 C16 H16A 120.9 . . ? C7 C17 C14 127.0(3) . . ? C7 C17 H17A 116.5 . . ? C14 C17 H17A 116.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.5(12) . . . . ? C1 Cl1 N11 O12 -178(4) . . . . ? O12 Cl1 N11 O11 -172.5(12) . . . . ? C1 Cl1 N11 O11 10(5) . . . . ? O11 Cl1 N11 C1 -10(5) . . . . ? O12 Cl1 N11 C1 178(4) . . . . ? O12 Cl1 O11 N11 135(6) . . . . ? C1 Cl1 O11 N11 -3.9(19) . . . . ? O12 N11 O11 Cl1 -9.1(14) . . . . ? C1 N11 O11 Cl1 174(3) . . . . ? O11 N11 O12 Cl1 4.9(8) . . . . ? C1 N11 O12 Cl1 -179(3) . . . . ? O11 Cl1 O12 N11 -139(6) . . . . ? C1 Cl1 O12 N11 0.9(16) . . . . ? Cl1 N11 C1 C6 6(4) . . . . ? O12 N11 C1 C6 -176.1(7) . . . . ? O11 N11 C1 C6 0.7(13) . . . . ? Cl1 N11 C1 C2 -174(3) . . . . ? O12 N11 C1 C2 3.2(12) . . . . ? O11 N11 C1 C2 -180.0(8) . . . . ? O12 N11 C1 Cl1 177(5) . . . . ? O11 N11 C1 Cl1 -6(3) . . . . ? O11 Cl1 C1 N11 172(4) . . . . ? O12 Cl1 C1 N11 -2(4) . . . . ? N11 Cl1 C1 C6 -174(4) . . . . ? O11 Cl1 C1 C6 -2.3(8) . . . . ? O12 Cl1 C1 C6 -176.1(3) . . . . ? N11 Cl1 C1 C2 6(4) . . . . ? O11 Cl1 C1 C2 178.2(7) . . . . ? O12 Cl1 C1 C2 4.4(4) . . . . ? N11 C1 C2 C3 -179.3(5) . . . . ? C6 C1 C2 C3 0.1(3) . . . . ? Cl1 C1 C2 C3 179.5(2) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C2 C3 C4 C7 -179.95(18) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C7 C4 C5 C6 -179.79(17) . . . . ? N11 C1 C6 C5 179.5(6) . . . . ? C2 C1 C6 C5 0.2(3) . . . . ? Cl1 C1 C6 C5 -179.3(2) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C3 C4 C7 C17 -4.5(4) . . . . ? C5 C4 C7 C17 176.0(2) . . . . ? O1 Cl11 N1 O2 -172.5(12) . . . . ? C11 Cl11 N1 O2 178(4) . . . . ? O2 Cl11 N1 O1 172.5(12) . . . . ? C11 Cl11 N1 O1 -10(5) . . . . ? O1 Cl11 N1 C11 10(5) . . . . ? O2 Cl11 N1 C11 -178(4) . . . . ? O2 Cl11 O1 N1 -135(6) . . . . ? C11 Cl11 O1 N1 3.9(19) . . . . ? O2 N1 O1 Cl11 9.1(14) . . . . ? C11 N1 O1 Cl11 -174(3) . . . . ? O1 N1 O2 Cl11 -4.9(8) . . . . ? C11 N1 O2 Cl11 179(3) . . . . ? O1 Cl11 O2 N1 139(6) . . . . ? C11 Cl11 O2 N1 -0.9(16) . . . . ? Cl11 N1 C11 C16 -6(4) . . . . ? O2 N1 C11 C16 176.1(7) . . . . ? O1 N1 C11 C16 -0.7(13) . . . . ? Cl11 N1 C11 C12 174(3) . . . . ? O2 N1 C11 C12 -3.2(12) . . . . ? O1 N1 C11 C12 180.0(8) . . . . ? O2 N1 C11 Cl11 -177(5) . . . . ? O1 N1 C11 Cl11 6(3) . . . . ? O1 Cl11 C11 N1 -172(4) . . . . ? O2 Cl11 C11 N1 2(4) . . . . ? N1 Cl11 C11 C16 174(4) . . . . ? O1 Cl11 C11 C16 2.3(8) . . . . ? O2 Cl11 C11 C16 176.1(3) . . . . ? N1 Cl11 C11 C12 -6(4) . . . . ? O1 Cl11 C11 C12 -178.2(7) . . . . ? O2 Cl11 C11 C12 -4.4(4) . . . . ? N1 C11 C12 C13 179.3(5) . . . . ? C16 C11 C12 C13 -0.1(3) . . . . ? Cl11 C11 C12 C13 -179.5(2) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? C12 C13 C14 C17 179.95(18) . . . . ? C13 C14 C15 C16 -0.7(3) . . . . ? C17 C14 C15 C16 179.79(17) . . . . ? N1 C11 C16 C15 -179.5(6) . . . . ? C12 C11 C16 C15 -0.2(3) . . . . ? Cl11 C11 C16 C15 179.3(2) . . . . ? C14 C15 C16 C11 0.6(3) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 4.5(4) . . . . ? C15 C14 C17 C7 -176.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.877 _diffrn_reflns_theta_full 27.81 _diffrn_measured_fraction_theta_full 0.877 _refine_diff_density_max 0.096 _refine_diff_density_min -0.094 _refine_diff_density_rms 0.025 # start Validation Reply Form _vrf_ABSTM02_CNS-MeCNII-small-P21_c ; PROBLEM: The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:23. ; _vrf_SYMMG02_CNS-MeCNII-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-MeCNII-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.88 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:23. ; _vrf_PLAT061_CNS-MeCNII-small-P21_c ; PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.08 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:23. ; # end Validation Reply Form #===END data_CNS-MeCNII-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761228' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9221(4) _cell_length_b 12.9733(12) _cell_length_c 12.2509(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.149(3) _cell_angle_gamma 90.00 _cell_volume 622.42(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3496 _cell_measurement_theta_min 3.140 _cell_measurement_theta_max 19.487 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.079036 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3478 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.81 _reflns_number_total 2315 _reflns_number_gt 900 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -6(4) _refine_ls_number_reflns 2315 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1610 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _refine_ls_shift/su_max 0.044 _refine_ls_shift/su_mean 0.007 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3703(13) -0.46108(13) -0.1746(5) 0.1140(19) Uani 0.49(2) 1 d P . . N11 N 0.365(3) -0.4160(6) -0.1745(12) 0.079(2) Uani 0.51(2) 1 d P . . O11 O 0.3165(19) -0.4977(5) -0.1234(5) 0.131(3) Uani 0.51(2) 1 d P . . O12 O 0.5006(9) -0.4124(3) -0.2572(3) 0.1156(13) Uani 0.51(2) 1 d P . . C1 C 0.2612(5) -0.32924(17) -0.12288(19) 0.0738(6) Uani 1 1 d . . . C2 C 0.3139(5) -0.23872(19) -0.17898(15) 0.0821(6) Uani 1 1 d . . . H2A H 0.4104 -0.2400 -0.2466 0.099 Uiso 1 1 calc R . . C3 C 0.2224(5) -0.14747(15) -0.13380(17) 0.0759(6) Uani 1 1 d . . . H3A H 0.2574 -0.0865 -0.1715 0.091 Uiso 1 1 calc R . . C4 C 0.0787(4) -0.14344(15) -0.03309(15) 0.0658(5) Uani 1 1 d . . . C5 C 0.0279(4) -0.23597(15) 0.02047(15) 0.0724(6) Uani 1 1 d . . . H5A H -0.0706 -0.2350 0.0878 0.087 Uiso 1 1 calc R . . C6 C 0.1188(5) -0.32915(14) -0.02298(17) 0.0782(6) Uani 1 1 d . . . H6A H 0.0848 -0.3904 0.0143 0.094 Uiso 1 1 calc R . . C7 C -0.0232(5) -0.04662(11) 0.01805(16) 0.0738(6) Uani 1 1 d . . . H7A H -0.1326 -0.0524 0.0832 0.089 Uiso 1 1 calc R . . Cl11 Cl -0.3703(13) 0.46108(13) 0.1746(5) 0.1140(19) Uani 0.51(2) 1 d P . . N1 N -0.365(3) 0.4160(6) 0.1745(12) 0.079(2) Uani 0.49(2) 1 d P . . O1 O -0.3165(19) 0.4977(5) 0.1234(5) 0.131(3) Uani 0.49(2) 1 d P . . O2 O -0.5006(9) 0.4124(3) 0.2572(3) 0.1156(13) Uani 0.49(2) 1 d P . . C11 C -0.2612(5) 0.32924(17) 0.12288(19) 0.0738(6) Uani 1 1 d . . . C12 C -0.3139(5) 0.23872(19) 0.17898(15) 0.0821(6) Uani 1 1 d . . . H12A H -0.4104 0.2400 0.2466 0.099 Uiso 1 1 calc R . . C13 C -0.2224(5) 0.14747(15) 0.13380(17) 0.0759(6) Uani 1 1 d . . . H13A H -0.2574 0.0865 0.1715 0.091 Uiso 1 1 calc R . . C14 C -0.0787(4) 0.14344(15) 0.03309(15) 0.0658(5) Uani 1 1 d . . . C15 C -0.0279(4) 0.23597(15) -0.02047(15) 0.0724(6) Uani 1 1 d . . . H15A H 0.0706 0.2350 -0.0878 0.087 Uiso 1 1 calc R . . C16 C -0.1188(5) 0.32915(14) 0.02298(17) 0.0782(6) Uani 1 1 d . . . H16A H -0.0848 0.3904 -0.0143 0.094 Uiso 1 1 calc R . . C17 C 0.0232(5) 0.04662(11) -0.01805(16) 0.0738(6) Uani 1 1 d . . . H17A H 0.1326 0.0524 -0.0832 0.089 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1191(17) 0.085(4) 0.138(3) -0.040(4) 0.002(2) 0.023(3) N11 0.072(3) 0.059(5) 0.106(6) 0.007(6) -0.003(3) 0.006(5) O11 0.164(4) 0.072(3) 0.160(6) 0.013(3) 0.037(3) 0.011(3) O12 0.156(3) 0.093(2) 0.101(3) -0.020(2) 0.035(2) 0.016(2) C1 0.0580(14) 0.0868(17) 0.0760(16) -0.0152(13) -0.0009(11) 0.0068(12) C2 0.0685(14) 0.1123(17) 0.0660(14) -0.0020(13) 0.0073(11) -0.0017(13) C3 0.0703(14) 0.0798(14) 0.0781(16) 0.0050(12) 0.0088(11) -0.0015(11) C4 0.0524(12) 0.0798(13) 0.0648(14) -0.0040(12) 0.0008(10) 0.0004(10) C5 0.0697(13) 0.0840(14) 0.0642(13) 0.0033(12) 0.0090(10) -0.0002(12) C6 0.0746(15) 0.0768(15) 0.0834(17) 0.0020(12) 0.0046(12) 0.0022(11) C7 0.0624(12) 0.0833(14) 0.0757(14) 0.0074(12) 0.0051(10) -0.0064(12) Cl11 0.1191(17) 0.085(4) 0.138(3) -0.040(4) 0.002(2) 0.023(3) N1 0.072(3) 0.059(5) 0.106(6) 0.007(6) -0.003(3) 0.006(5) O1 0.164(4) 0.072(3) 0.160(6) 0.013(3) 0.037(3) 0.011(3) O2 0.156(3) 0.093(2) 0.101(3) -0.020(2) 0.035(2) 0.016(2) C11 0.0580(14) 0.0868(17) 0.0760(16) -0.0152(13) -0.0009(11) 0.0068(12) C12 0.0685(14) 0.1123(17) 0.0660(14) -0.0020(13) 0.0073(11) -0.0017(13) C13 0.0703(14) 0.0798(14) 0.0781(16) 0.0050(12) 0.0088(11) -0.0015(11) C14 0.0524(12) 0.0798(13) 0.0648(14) -0.0040(12) 0.0008(10) 0.0004(10) C15 0.0697(13) 0.0840(14) 0.0642(13) 0.0033(12) 0.0090(10) -0.0002(12) C16 0.0746(15) 0.0768(15) 0.0834(17) 0.0020(12) 0.0046(12) 0.0022(11) C17 0.0624(12) 0.0833(14) 0.0757(14) 0.0074(12) 0.0051(10) -0.0064(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.585(8) . ? Cl1 O11 0.824(6) . ? Cl1 O12 1.319(6) . ? Cl1 C1 1.881(3) . ? N11 O12 1.171(14) . ? N11 O11 1.250(16) . ? N11 C1 1.364(8) . ? C1 C6 1.373(2) . ? C1 C2 1.382(2) . ? C2 C3 1.363(2) . ? C2 H2A 0.9300 . ? C3 C4 1.385(2) . ? C3 H3A 0.9300 . ? C4 C5 1.388(2) . ? C4 C7 1.469(2) . ? C5 C6 1.376(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.304(3) . ? C7 H7A 0.9300 . ? Cl11 N1 0.585(8) . ? Cl11 O1 0.824(6) . ? Cl11 O2 1.319(6) . ? Cl11 C11 1.881(3) . ? N1 O2 1.171(14) . ? N1 O1 1.250(16) . ? N1 C11 1.364(8) . ? C11 C16 1.373(2) . ? C11 C12 1.382(2) . ? C12 C13 1.363(2) . ? C12 H12A 0.9300 . ? C13 C14 1.385(2) . ? C13 H13A 0.9300 . ? C14 C15 1.388(2) . ? C14 C17 1.469(2) . ? C15 C16 1.376(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 124(2) . . ? N11 Cl1 O12 62.6(18) . . ? O11 Cl1 O12 170.5(8) . . ? N11 Cl1 C1 23.3(17) . . ? O11 Cl1 C1 101.3(8) . . ? O12 Cl1 C1 85.9(2) . . ? Cl1 N11 O12 91.1(18) . . ? Cl1 N11 O11 32.9(16) . . ? O12 N11 O11 123.7(7) . . ? Cl1 N11 C1 147(2) . . ? O12 N11 C1 121.9(9) . . ? O11 N11 C1 114.2(10) . . ? Cl1 O11 N11 22.7(8) . . ? N11 O12 Cl1 26.3(4) . . ? N11 C1 C6 124.0(6) . . ? N11 C1 C2 114.5(6) . . ? C6 C1 C2 121.5(2) . . ? N11 C1 Cl1 9.8(7) . . ? C6 C1 Cl1 114.3(3) . . ? C2 C1 Cl1 124.2(3) . . ? C3 C2 C1 119.09(19) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 121.6(2) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 117.68(19) . . ? C3 C4 C7 123.1(2) . . ? C5 C4 C7 119.25(18) . . ? C6 C5 C4 122.02(18) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C1 C6 C5 118.2(2) . . ? C1 C6 H6A 120.9 . . ? C5 C6 H6A 120.9 . . ? C17 C7 C4 127.0(3) . . ? C17 C7 H7A 116.5 . . ? C4 C7 H7A 116.5 . . ? N1 Cl11 O1 124(2) . . ? N1 Cl11 O2 62.6(18) . . ? O1 Cl11 O2 170.5(8) . . ? N1 Cl11 C11 23.3(17) . . ? O1 Cl11 C11 101.3(8) . . ? O2 Cl11 C11 85.9(2) . . ? Cl11 N1 O2 91.1(18) . . ? Cl11 N1 O1 32.9(16) . . ? O2 N1 O1 123.7(7) . . ? Cl11 N1 C11 147(2) . . ? O2 N1 C11 121.9(9) . . ? O1 N1 C11 114.2(10) . . ? Cl11 O1 N1 22.7(8) . . ? N1 O2 Cl11 26.3(4) . . ? N1 C11 C16 124.0(6) . . ? N1 C11 C12 114.5(6) . . ? C16 C11 C12 121.5(2) . . ? N1 C11 Cl11 9.8(7) . . ? C16 C11 Cl11 114.3(3) . . ? C12 C11 Cl11 124.2(3) . . ? C13 C12 C11 119.09(19) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C14 121.6(2) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C13 C14 C15 117.68(19) . . ? C13 C14 C17 123.1(2) . . ? C15 C14 C17 119.25(18) . . ? C16 C15 C14 122.02(18) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C11 C16 C15 118.2(2) . . ? C11 C16 H16A 120.9 . . ? C15 C16 H16A 120.9 . . ? C7 C17 C14 127.0(3) . . ? C7 C17 H17A 116.5 . . ? C14 C17 H17A 116.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.5(12) . . . . ? C1 Cl1 N11 O12 -178(4) . . . . ? O12 Cl1 N11 O11 -172.5(12) . . . . ? C1 Cl1 N11 O11 10(5) . . . . ? O11 Cl1 N11 C1 -10(5) . . . . ? O12 Cl1 N11 C1 178(4) . . . . ? O12 Cl1 O11 N11 135(6) . . . . ? C1 Cl1 O11 N11 -3.9(19) . . . . ? O12 N11 O11 Cl1 -9.1(14) . . . . ? C1 N11 O11 Cl1 174(3) . . . . ? O11 N11 O12 Cl1 4.9(8) . . . . ? C1 N11 O12 Cl1 -179(3) . . . . ? O11 Cl1 O12 N11 -139(6) . . . . ? C1 Cl1 O12 N11 0.9(16) . . . . ? Cl1 N11 C1 C6 7(4) . . . . ? O12 N11 C1 C6 -176.2(7) . . . . ? O11 N11 C1 C6 0.7(13) . . . . ? Cl1 N11 C1 C2 -174(3) . . . . ? O12 N11 C1 C2 3.2(12) . . . . ? O11 N11 C1 C2 -180.0(8) . . . . ? O12 N11 C1 Cl1 177(5) . . . . ? O11 N11 C1 Cl1 -6(3) . . . . ? O11 Cl1 C1 N11 172(4) . . . . ? O12 Cl1 C1 N11 -2(4) . . . . ? N11 Cl1 C1 C6 -174(4) . . . . ? O11 Cl1 C1 C6 -2.3(8) . . . . ? O12 Cl1 C1 C6 -176.1(3) . . . . ? N11 Cl1 C1 C2 6(4) . . . . ? O11 Cl1 C1 C2 178.2(7) . . . . ? O12 Cl1 C1 C2 4.4(4) . . . . ? N11 C1 C2 C3 -179.3(5) . . . . ? C6 C1 C2 C3 0.1(3) . . . . ? Cl1 C1 C2 C3 179.5(2) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C2 C3 C4 C7 -179.95(18) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C7 C4 C5 C6 -179.79(17) . . . . ? N11 C1 C6 C5 179.5(6) . . . . ? C2 C1 C6 C5 0.2(3) . . . . ? Cl1 C1 C6 C5 -179.3(2) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C3 C4 C7 C17 -4.5(4) . . . . ? C5 C4 C7 C17 176.0(2) . . . . ? O1 Cl11 N1 O2 -172.5(12) . . . . ? C11 Cl11 N1 O2 178(4) . . . . ? O2 Cl11 N1 O1 172.5(12) . . . . ? C11 Cl11 N1 O1 -10(5) . . . . ? O1 Cl11 N1 C11 10(5) . . . . ? O2 Cl11 N1 C11 -178(4) . . . . ? O2 Cl11 O1 N1 -135(6) . . . . ? C11 Cl11 O1 N1 3.9(19) . . . . ? O2 N1 O1 Cl11 9.1(14) . . . . ? C11 N1 O1 Cl11 -174(3) . . . . ? O1 N1 O2 Cl11 -4.9(8) . . . . ? C11 N1 O2 Cl11 179(3) . . . . ? O1 Cl11 O2 N1 139(6) . . . . ? C11 Cl11 O2 N1 -0.9(16) . . . . ? Cl11 N1 C11 C16 -7(4) . . . . ? O2 N1 C11 C16 176.2(7) . . . . ? O1 N1 C11 C16 -0.7(13) . . . . ? Cl11 N1 C11 C12 174(3) . . . . ? O2 N1 C11 C12 -3.2(12) . . . . ? O1 N1 C11 C12 180.0(8) . . . . ? O2 N1 C11 Cl11 -177(5) . . . . ? O1 N1 C11 Cl11 6(3) . . . . ? O1 Cl11 C11 N1 -172(4) . . . . ? O2 Cl11 C11 N1 2(4) . . . . ? N1 Cl11 C11 C16 174(4) . . . . ? O1 Cl11 C11 C16 2.3(8) . . . . ? O2 Cl11 C11 C16 176.1(3) . . . . ? N1 Cl11 C11 C12 -6(4) . . . . ? O1 Cl11 C11 C12 -178.2(7) . . . . ? O2 Cl11 C11 C12 -4.4(4) . . . . ? N1 C11 C12 C13 179.3(5) . . . . ? C16 C11 C12 C13 -0.1(3) . . . . ? Cl11 C11 C12 C13 -179.5(2) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? C12 C13 C14 C17 179.95(18) . . . . ? C13 C14 C15 C16 -0.7(3) . . . . ? C17 C14 C15 C16 179.79(17) . . . . ? N1 C11 C16 C15 -179.5(6) . . . . ? C12 C11 C16 C15 -0.2(3) . . . . ? Cl11 C11 C16 C15 179.3(2) . . . . ? C14 C15 C16 C11 0.6(3) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 4.5(4) . . . . ? C15 C14 C17 C7 -176.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 27.81 _diffrn_measured_fraction_theta_full 0.914 _refine_diff_density_max 0.096 _refine_diff_density_min -0.095 _refine_diff_density_rms 0.025 # start Validation Reply Form _vrf_ABSTM02_CNS-MeCNII-small-P21 ; PROBLEM: The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:23. ; _vrf_SYMMG02_CNS-MeCNII-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-MeCNII-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.91 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:23. ; _vrf_PLAT061_CNS-MeCNII-small-P21 ; PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.08 RESPONSE: This is mainly due to the overall poor quality of the data at higher resolution. The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:23. ; # end Validation Reply Form #===END data_CNS-DMFI-small-P21_c _database_code_depnum_ccdc_archive 'CCDC 761229' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9208(2) _cell_length_b 12.9696(7) _cell_length_c 12.2508(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.138(2) _cell_angle_gamma 90.00 _cell_volume 622.03(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3460 _cell_measurement_theta_min 3.1415 _cell_measurement_theta_max 23.005 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.725572 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3447 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.75 _reflns_number_total 2286 _reflns_number_gt 1159 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.0491P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 2286 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1076 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3704(10) -0.46130(11) -0.1755(3) 0.1178(13) Uani 0.50 1 d P . . N11 N 0.365(2) -0.4161(4) -0.1725(7) 0.0787(13) Uani 0.50 1 d P . . O11 O 0.3125(15) -0.4972(4) -0.1235(4) 0.1369(19) Uani 0.50 1 d P . . O12 O 0.4982(7) -0.4125(2) -0.2582(2) 0.1153(10) Uani 0.50 1 d P . . C1 C 0.2609(3) -0.32957(13) -0.12299(14) 0.0742(4) Uani 1 1 d . . . C2 C 0.3145(4) -0.23939(15) -0.17896(12) 0.0824(5) Uani 1 1 d . . . H2A H 0.4123 -0.2409 -0.2464 0.099 Uiso 1 1 calc R . . C3 C 0.2223(4) -0.14762(13) -0.13425(13) 0.0778(5) Uani 1 1 d . . . H3A H 0.2565 -0.0868 -0.1723 0.093 Uiso 1 1 calc R . . C4 C 0.0785(3) -0.14329(12) -0.03312(11) 0.0668(4) Uani 1 1 d . . . C5 C 0.0279(3) -0.23612(12) 0.02036(12) 0.0744(4) Uani 1 1 d . . . H5A H -0.0709 -0.2352 0.0877 0.089 Uiso 1 1 calc R . . C6 C 0.1192(4) -0.32936(12) -0.02300(13) 0.0786(5) Uani 1 1 d . . . H6A H 0.0858 -0.3906 0.0144 0.094 Uiso 1 1 calc R . . C7 C -0.0238(4) -0.04647(10) 0.01806(13) 0.0745(4) Uani 1 1 d . . . H7A H -0.1340 -0.0522 0.0831 0.089 Uiso 1 1 calc R . . Cl11 Cl -0.3704(10) 0.46130(11) 0.1755(3) 0.1178(13) Uani 0.50 1 d P . . N1 N -0.365(2) 0.4161(4) 0.1725(7) 0.0787(13) Uani 0.50 1 d P . . O1 O -0.3125(15) 0.4972(4) 0.1235(4) 0.1369(19) Uani 0.50 1 d P . . O2 O -0.4982(7) 0.4125(2) 0.2582(2) 0.1153(10) Uani 0.50 1 d P . . C11 C -0.2609(3) 0.32957(13) 0.12299(14) 0.0742(4) Uani 1 1 d . . . C12 C -0.3145(4) 0.23939(15) 0.17896(12) 0.0824(5) Uani 1 1 d . . . H12A H -0.4123 0.2409 0.2464 0.099 Uiso 1 1 calc R . . C13 C -0.2223(4) 0.14762(13) 0.13425(13) 0.0778(5) Uani 1 1 d . . . H13A H -0.2565 0.0868 0.1723 0.093 Uiso 1 1 calc R . . C14 C -0.0785(3) 0.14329(12) 0.03312(11) 0.0668(4) Uani 1 1 d . . . C15 C -0.0279(3) 0.23612(12) -0.02036(12) 0.0744(4) Uani 1 1 d . . . H15A H 0.0709 0.2352 -0.0877 0.089 Uiso 1 1 calc R . . C16 C -0.1192(4) 0.32936(12) 0.02300(13) 0.0786(5) Uani 1 1 d . . . H16A H -0.0858 0.3906 -0.0144 0.094 Uiso 1 1 calc R . . C17 C 0.0238(4) 0.04647(10) -0.01806(13) 0.0745(4) Uani 1 1 d . . . H17A H 0.1340 0.0522 -0.0831 0.089 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1166(12) 0.091(2) 0.146(2) -0.050(2) 0.0050(13) 0.0226(18) N11 0.079(2) 0.062(4) 0.095(4) -0.004(3) -0.002(2) 0.005(3) O11 0.168(3) 0.080(3) 0.165(4) 0.009(2) 0.039(3) 0.010(2) O12 0.154(3) 0.0920(19) 0.103(2) -0.0237(16) 0.0384(18) 0.0143(17) C1 0.0591(9) 0.0852(12) 0.0777(11) -0.0134(9) -0.0003(8) 0.0053(8) C2 0.0703(10) 0.1079(14) 0.0697(11) -0.0054(10) 0.0102(8) 0.0003(9) C3 0.0714(10) 0.0857(11) 0.0765(11) 0.0078(9) 0.0079(8) -0.0027(8) C4 0.0540(8) 0.0777(10) 0.0685(10) -0.0032(8) 0.0017(7) -0.0010(7) C5 0.0710(10) 0.0835(11) 0.0695(10) 0.0012(9) 0.0101(7) -0.0008(8) C6 0.0761(10) 0.0780(11) 0.0818(12) 0.0026(9) 0.0053(8) 0.0028(8) C7 0.0639(9) 0.0855(11) 0.0743(10) 0.0053(8) 0.0058(7) -0.0039(9) Cl11 0.1166(12) 0.091(2) 0.146(2) -0.050(2) 0.0050(13) 0.0226(18) N1 0.079(2) 0.062(4) 0.095(4) -0.004(3) -0.002(2) 0.005(3) O1 0.168(3) 0.080(3) 0.165(4) 0.009(2) 0.039(3) 0.010(2) O2 0.154(3) 0.0920(19) 0.103(2) -0.0237(16) 0.0384(18) 0.0143(17) C11 0.0591(9) 0.0852(12) 0.0777(11) -0.0134(9) -0.0003(8) 0.0053(8) C12 0.0703(10) 0.1079(14) 0.0697(11) -0.0054(10) 0.0102(8) 0.0003(9) C13 0.0714(10) 0.0857(11) 0.0765(11) 0.0078(9) 0.0079(8) -0.0027(8) C14 0.0540(8) 0.0777(10) 0.0685(10) -0.0032(8) 0.0017(7) -0.0010(7) C15 0.0710(10) 0.0835(11) 0.0695(10) 0.0012(9) 0.0101(7) -0.0008(8) C16 0.0761(10) 0.0780(11) 0.0818(12) 0.0026(9) 0.0053(8) 0.0028(8) C17 0.0639(9) 0.0855(11) 0.0743(10) 0.0053(8) 0.0058(7) -0.0039(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.588(5) . ? Cl1 O11 0.830(4) . ? Cl1 O12 1.317(4) . ? Cl1 C1 1.883(2) . ? N11 O12 1.200(9) . ? N11 O11 1.234(11) . ? N11 C1 1.349(5) . ? C1 C6 1.372(2) . ? C1 C2 1.378(2) . ? C2 C3 1.367(2) . ? C2 H2A 0.9300 . ? C3 C4 1.3900(19) . ? C3 H3A 0.9300 . ? C4 C5 1.3901(18) . ? C4 C7 1.4692(19) . ? C5 C6 1.3760(18) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.301(2) . ? C7 H7A 0.9300 . ? Cl11 N1 0.588(5) . ? Cl11 O1 0.830(4) . ? Cl11 O2 1.317(4) . ? Cl11 C11 1.883(2) . ? N1 O2 1.200(9) . ? N1 O1 1.234(11) . ? N1 C11 1.349(5) . ? C11 C16 1.372(2) . ? C11 C12 1.378(2) . ? C12 C13 1.367(2) . ? C12 H12A 0.9300 . ? C13 C14 1.3900(19) . ? C13 H13A 0.9300 . ? C14 C15 1.3901(18) . ? C14 C17 1.4692(19) . ? C15 C16 1.3760(18) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 120.0(15) . . ? N11 Cl1 O12 65.5(11) . . ? O11 Cl1 O12 172.3(6) . . ? N11 Cl1 C1 20.7(10) . . ? O11 Cl1 C1 99.8(6) . . ? O12 Cl1 C1 86.00(16) . . ? Cl1 N11 O12 88.0(10) . . ? Cl1 N11 O11 35.6(10) . . ? O12 N11 O11 123.5(5) . . ? Cl1 N11 C1 150.5(15) . . ? O12 N11 C1 121.2(6) . . ? O11 N11 C1 115.4(6) . . ? Cl1 O11 N11 24.4(5) . . ? N11 O12 Cl1 26.5(2) . . ? N11 C1 C6 123.4(4) . . ? N11 C1 C2 115.1(4) . . ? C6 C1 C2 121.52(16) . . ? N11 C1 Cl1 8.8(5) . . ? C6 C1 Cl1 114.67(19) . . ? C2 C1 Cl1 123.80(17) . . ? C3 C2 C1 119.26(15) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.42(16) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.41(15) . . ? C5 C4 C7 119.33(13) . . ? C3 C4 C7 123.25(15) . . ? C6 C5 C4 122.17(14) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C1 C6 C5 118.22(15) . . ? C1 C6 H6A 120.9 . . ? C5 C6 H6A 120.9 . . ? C17 C7 C4 126.82(19) . . ? C17 C7 H7A 116.6 . . ? C4 C7 H7A 116.6 . . ? N1 Cl11 O1 120.0(15) . . ? N1 Cl11 O2 65.5(11) . . ? O1 Cl11 O2 172.3(6) . . ? N1 Cl11 C11 20.7(10) . . ? O1 Cl11 C11 99.8(6) . . ? O2 Cl11 C11 86.00(16) . . ? Cl11 N1 O2 88.0(10) . . ? Cl11 N1 O1 35.6(10) . . ? O2 N1 O1 123.5(5) . . ? Cl11 N1 C11 150.5(15) . . ? O2 N1 C11 121.2(6) . . ? O1 N1 C11 115.4(6) . . ? Cl11 O1 N1 24.4(5) . . ? N1 O2 Cl11 26.5(2) . . ? N1 C11 C16 123.4(4) . . ? N1 C11 C12 115.1(4) . . ? C16 C11 C12 121.52(16) . . ? N1 C11 Cl11 8.8(5) . . ? C16 C11 Cl11 114.67(19) . . ? C12 C11 Cl11 123.80(17) . . ? C13 C12 C11 119.26(15) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 121.42(16) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 117.41(15) . . ? C15 C14 C17 119.33(13) . . ? C13 C14 C17 123.25(15) . . ? C16 C15 C14 122.17(14) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C11 C16 C15 118.22(15) . . ? C11 C16 H16A 120.9 . . ? C15 C16 H16A 120.9 . . ? C7 C17 C14 126.82(19) . . ? C7 C17 H17A 116.6 . . ? C14 C17 H17A 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 173.9(8) . . . . ? C1 Cl1 N11 O12 -173(3) . . . . ? O12 Cl1 N11 O11 -173.9(8) . . . . ? C1 Cl1 N11 O11 13(3) . . . . ? O11 Cl1 N11 C1 -13(3) . . . . ? O12 Cl1 N11 C1 173(3) . . . . ? O12 Cl1 O11 N11 134(6) . . . . ? C1 Cl1 O11 N11 -4.7(12) . . . . ? O12 N11 O11 Cl1 -7.3(10) . . . . ? C1 N11 O11 Cl1 172.8(19) . . . . ? O11 N11 O12 Cl1 4.2(6) . . . . ? C1 N11 O12 Cl1 -175.8(17) . . . . ? O11 Cl1 O12 N11 -137(5) . . . . ? C1 Cl1 O12 N11 2.6(10) . . . . ? Cl1 N11 C1 C6 11(3) . . . . ? O12 N11 C1 C6 -177.4(5) . . . . ? O11 N11 C1 C6 2.6(9) . . . . ? Cl1 N11 C1 C2 -170(3) . . . . ? O12 N11 C1 C2 1.1(8) . . . . ? O11 N11 C1 C2 -178.9(6) . . . . ? O12 N11 C1 Cl1 171(3) . . . . ? O11 N11 C1 Cl1 -9(2) . . . . ? O11 Cl1 C1 N11 168(3) . . . . ? O12 Cl1 C1 N11 -7(3) . . . . ? N11 Cl1 C1 C6 -170(3) . . . . ? O11 Cl1 C1 C6 -1.5(6) . . . . ? O12 Cl1 C1 C6 -176.41(19) . . . . ? N11 Cl1 C1 C2 11(3) . . . . ? O11 Cl1 C1 C2 178.8(5) . . . . ? O12 Cl1 C1 C2 3.9(3) . . . . ? N11 C1 C2 C3 -179.0(4) . . . . ? C6 C1 C2 C3 -0.5(2) . . . . ? Cl1 C1 C2 C3 179.26(18) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C5 -0.8(2) . . . . ? C2 C3 C4 C7 179.90(14) . . . . ? C3 C4 C5 C6 0.9(2) . . . . ? C7 C4 C5 C6 -179.76(13) . . . . ? N11 C1 C6 C5 178.9(4) . . . . ? C2 C1 C6 C5 0.6(2) . . . . ? Cl1 C1 C6 C5 -179.19(17) . . . . ? C4 C5 C6 C1 -0.8(2) . . . . ? C5 C4 C7 C17 175.78(19) . . . . ? C3 C4 C7 C17 -4.9(3) . . . . ? O1 Cl11 N1 O2 -173.9(8) . . . . ? C11 Cl11 N1 O2 173(3) . . . . ? O2 Cl11 N1 O1 173.9(8) . . . . ? C11 Cl11 N1 O1 -13(3) . . . . ? O1 Cl11 N1 C11 13(3) . . . . ? O2 Cl11 N1 C11 -173(3) . . . . ? O2 Cl11 O1 N1 -134(6) . . . . ? C11 Cl11 O1 N1 4.7(12) . . . . ? O2 N1 O1 Cl11 7.3(10) . . . . ? C11 N1 O1 Cl11 -172.8(19) . . . . ? O1 N1 O2 Cl11 -4.2(6) . . . . ? C11 N1 O2 Cl11 175.8(17) . . . . ? O1 Cl11 O2 N1 137(5) . . . . ? C11 Cl11 O2 N1 -2.6(10) . . . . ? Cl11 N1 C11 C16 -11(3) . . . . ? O2 N1 C11 C16 177.4(5) . . . . ? O1 N1 C11 C16 -2.6(9) . . . . ? Cl11 N1 C11 C12 170(3) . . . . ? O2 N1 C11 C12 -1.1(8) . . . . ? O1 N1 C11 C12 178.9(6) . . . . ? O2 N1 C11 Cl11 -171(3) . . . . ? O1 N1 C11 Cl11 9(2) . . . . ? O1 Cl11 C11 N1 -168(3) . . . . ? O2 Cl11 C11 N1 7(3) . . . . ? N1 Cl11 C11 C16 170(3) . . . . ? O1 Cl11 C11 C16 1.5(6) . . . . ? O2 Cl11 C11 C16 176.41(19) . . . . ? N1 Cl11 C11 C12 -11(3) . . . . ? O1 Cl11 C11 C12 -178.8(5) . . . . ? O2 Cl11 C11 C12 -3.9(3) . . . . ? N1 C11 C12 C13 179.0(4) . . . . ? C16 C11 C12 C13 0.5(2) . . . . ? Cl11 C11 C12 C13 -179.26(18) . . . . ? C11 C12 C13 C14 -0.6(2) . . . . ? C12 C13 C14 C15 0.8(2) . . . . ? C12 C13 C14 C17 -179.90(14) . . . . ? C13 C14 C15 C16 -0.9(2) . . . . ? C17 C14 C15 C16 179.76(13) . . . . ? N1 C11 C16 C15 -178.9(4) . . . . ? C12 C11 C16 C15 -0.6(2) . . . . ? Cl11 C11 C16 C15 179.19(17) . . . . ? C14 C15 C16 C11 0.8(2) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.78(19) . . . . ? C13 C14 C17 C7 4.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.879 _diffrn_reflns_theta_full 27.75 _diffrn_measured_fraction_theta_full 0.879 _refine_diff_density_max 0.100 _refine_diff_density_min -0.083 _refine_diff_density_rms 0.023 # start Validation Reply Form _vrf_SYMMG02_CNS-DMFI-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-DMFI-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.88 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:23. ; # end Validation Reply Form #===END data_CNS-DMFI-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761230' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9208(2) _cell_length_b 12.9696(7) _cell_length_c 12.2508(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.138(2) _cell_angle_gamma 90.00 _cell_volume 622.03(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3460 _cell_measurement_theta_min 3.1415 _cell_measurement_theta_max 23.005 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.725572 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3447 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.75 _reflns_number_total 2286 _reflns_number_gt 1159 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.0491P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(4) _refine_ls_number_reflns 2286 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1068 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.0955 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3704(9) -0.46128(11) -0.1755(3) 0.1178(13) Uani 0.466(3) 1 d P . . N11 N 0.365(2) -0.4161(4) -0.1725(6) 0.0791(13) Uani 0.534(3) 1 d P . . O11 O 0.3125(15) -0.4971(4) -0.1235(4) 0.1364(19) Uani 0.534(3) 1 d P . . O12 O 0.4982(7) -0.4126(2) -0.2582(2) 0.1150(10) Uani 0.534(3) 1 d P . . C1 C 0.2609(3) -0.32956(13) -0.12300(13) 0.0742(4) Uani 1 1 d . . . C2 C 0.3145(4) -0.23937(15) -0.17902(12) 0.0823(5) Uani 1 1 d . . . H2A H 0.4123 -0.2409 -0.2465 0.099 Uiso 1 1 calc R . . C3 C 0.2222(4) -0.14766(13) -0.13424(12) 0.0779(5) Uani 1 1 d . . . H3A H 0.2565 -0.0868 -0.1723 0.093 Uiso 1 1 calc R . . C4 C 0.0785(3) -0.14327(12) -0.03314(11) 0.0667(4) Uani 1 1 d . . . C5 C 0.0279(3) -0.23613(12) 0.02036(12) 0.0745(4) Uani 1 1 d . . . H5A H -0.0709 -0.2352 0.0877 0.089 Uiso 1 1 calc R . . C6 C 0.1193(4) -0.32931(12) -0.02300(13) 0.0785(5) Uani 1 1 d . . . H6A H 0.0859 -0.3905 0.0145 0.094 Uiso 1 1 calc R . . C7 C -0.0237(4) -0.04648(10) 0.01803(13) 0.0744(4) Uani 1 1 d . . . H7A H -0.1340 -0.0522 0.0831 0.089 Uiso 1 1 calc R . . Cl11 Cl -0.3704(9) 0.46128(11) 0.1755(3) 0.1178(13) Uani 0.534(3) 1 d P . . N1 N -0.365(2) 0.4161(4) 0.1725(6) 0.0791(13) Uani 0.466(3) 1 d P . . O1 O -0.3125(15) 0.4971(4) 0.1235(4) 0.1364(19) Uani 0.466(3) 1 d P . . O2 O -0.4982(7) 0.4126(2) 0.2582(2) 0.1150(10) Uani 0.466(3) 1 d P . . C11 C -0.2609(3) 0.32956(13) 0.12300(13) 0.0742(4) Uani 1 1 d . . . C12 C -0.3145(4) 0.23937(15) 0.17902(12) 0.0823(5) Uani 1 1 d . . . H12A H -0.4123 0.2409 0.2465 0.099 Uiso 1 1 calc R . . C13 C -0.2222(4) 0.14766(13) 0.13424(12) 0.0779(5) Uani 1 1 d . . . H13A H -0.2565 0.0868 0.1723 0.093 Uiso 1 1 calc R . . C14 C -0.0785(3) 0.14327(12) 0.03314(11) 0.0667(4) Uani 1 1 d . . . C15 C -0.0279(3) 0.23613(12) -0.02036(12) 0.0745(4) Uani 1 1 d . . . H15A H 0.0709 0.2352 -0.0877 0.089 Uiso 1 1 calc R . . C16 C -0.1193(4) 0.32931(12) 0.02300(13) 0.0785(5) Uani 1 1 d . . . H16A H -0.0859 0.3905 -0.0145 0.094 Uiso 1 1 calc R . . C17 C 0.0237(4) 0.04648(10) -0.01803(13) 0.0744(4) Uani 1 1 d . . . H17A H 0.1340 0.0522 -0.0831 0.089 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1165(12) 0.091(2) 0.146(2) -0.050(2) 0.0052(13) 0.0224(18) N11 0.079(2) 0.062(4) 0.096(4) -0.005(3) -0.002(2) 0.005(3) O11 0.167(3) 0.081(3) 0.165(4) 0.009(2) 0.039(3) 0.010(2) O12 0.154(3) 0.0916(19) 0.103(2) -0.0232(16) 0.0389(18) 0.0141(17) C1 0.0589(9) 0.0855(12) 0.0778(11) -0.0135(9) -0.0004(8) 0.0054(8) C2 0.0702(10) 0.1078(14) 0.0697(10) -0.0054(9) 0.0103(8) 0.0003(9) C3 0.0712(10) 0.0861(11) 0.0767(11) 0.0080(9) 0.0077(8) -0.0028(8) C4 0.0540(8) 0.0779(10) 0.0681(10) -0.0032(8) 0.0019(7) -0.0010(7) C5 0.0709(9) 0.0838(11) 0.0695(10) 0.0012(9) 0.0101(7) -0.0007(8) C6 0.0761(10) 0.0780(11) 0.0817(12) 0.0027(9) 0.0054(8) 0.0026(8) C7 0.0639(9) 0.0852(11) 0.0744(10) 0.0052(8) 0.0057(7) -0.0038(9) Cl11 0.1165(12) 0.091(2) 0.146(2) -0.050(2) 0.0052(13) 0.0224(18) N1 0.079(2) 0.062(4) 0.096(4) -0.005(3) -0.002(2) 0.005(3) O1 0.167(3) 0.081(3) 0.165(4) 0.009(2) 0.039(3) 0.010(2) O2 0.154(3) 0.0916(19) 0.103(2) -0.0232(16) 0.0389(18) 0.0141(17) C11 0.0589(9) 0.0855(12) 0.0778(11) -0.0135(9) -0.0004(8) 0.0054(8) C12 0.0702(10) 0.1078(14) 0.0697(10) -0.0054(9) 0.0103(8) 0.0003(9) C13 0.0712(10) 0.0861(11) 0.0767(11) 0.0080(9) 0.0077(8) -0.0028(8) C14 0.0540(8) 0.0779(10) 0.0681(10) -0.0032(8) 0.0019(7) -0.0010(7) C15 0.0709(9) 0.0838(11) 0.0695(10) 0.0012(9) 0.0101(7) -0.0007(8) C16 0.0761(10) 0.0780(11) 0.0817(12) 0.0027(9) 0.0054(8) 0.0026(8) C17 0.0639(9) 0.0852(11) 0.0744(10) 0.0052(8) 0.0057(7) -0.0038(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.588(5) . ? Cl1 O11 0.830(4) . ? Cl1 O12 1.316(4) . ? Cl1 C1 1.883(2) . ? N11 O12 1.200(8) . ? N11 O11 1.232(11) . ? N11 C1 1.349(5) . ? C1 C6 1.373(2) . ? C1 C2 1.378(2) . ? C2 C3 1.367(2) . ? C2 H2A 0.9300 . ? C3 C4 1.3896(19) . ? C3 H3A 0.9300 . ? C4 C5 1.3905(18) . ? C4 C7 1.4688(19) . ? C5 C6 1.3754(18) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.301(2) . ? C7 H7A 0.9300 . ? Cl11 N1 0.588(5) . ? Cl11 O1 0.830(4) . ? Cl11 O2 1.316(4) . ? Cl11 C11 1.883(2) . ? N1 O2 1.200(8) . ? N1 O1 1.232(11) . ? N1 C11 1.349(5) . ? C11 C16 1.373(2) . ? C11 C12 1.378(2) . ? C12 C13 1.367(2) . ? C12 H12A 0.9300 . ? C13 C14 1.3896(19) . ? C13 H13A 0.9300 . ? C14 C15 1.3905(18) . ? C14 C17 1.4688(19) . ? C15 C16 1.3754(18) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 119.8(15) . . ? N11 Cl1 O12 65.6(11) . . ? O11 Cl1 O12 172.3(6) . . ? N11 Cl1 C1 20.6(10) . . ? O11 Cl1 C1 99.7(6) . . ? O12 Cl1 C1 86.06(16) . . ? Cl1 N11 O12 87.9(10) . . ? Cl1 N11 O11 35.8(10) . . ? O12 N11 O11 123.4(5) . . ? Cl1 N11 C1 150.6(15) . . ? O12 N11 C1 121.2(6) . . ? O11 N11 C1 115.4(6) . . ? Cl1 O11 N11 24.4(5) . . ? N11 O12 Cl1 26.5(2) . . ? N11 C1 C6 123.4(4) . . ? N11 C1 C2 115.1(4) . . ? C6 C1 C2 121.51(15) . . ? N11 C1 Cl1 8.8(5) . . ? C6 C1 Cl1 114.71(19) . . ? C2 C1 Cl1 123.78(17) . . ? C3 C2 C1 119.20(14) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.50(16) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.39(15) . . ? C5 C4 C7 119.32(13) . . ? C3 C4 C7 123.29(15) . . ? C6 C5 C4 122.15(14) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C1 C6 C5 118.26(15) . . ? C1 C6 H6A 120.9 . . ? C5 C6 H6A 120.9 . . ? C17 C7 C4 126.85(19) . . ? C17 C7 H7A 116.6 . . ? C4 C7 H7A 116.6 . . ? N1 Cl11 O1 119.8(15) . . ? N1 Cl11 O2 65.6(11) . . ? O1 Cl11 O2 172.3(6) . . ? N1 Cl11 C11 20.6(10) . . ? O1 Cl11 C11 99.7(6) . . ? O2 Cl11 C11 86.06(16) . . ? Cl11 N1 O2 87.9(10) . . ? Cl11 N1 O1 35.8(10) . . ? O2 N1 O1 123.4(5) . . ? Cl11 N1 C11 150.6(15) . . ? O2 N1 C11 121.2(6) . . ? O1 N1 C11 115.4(6) . . ? Cl11 O1 N1 24.4(5) . . ? N1 O2 Cl11 26.5(2) . . ? N1 C11 C16 123.4(4) . . ? N1 C11 C12 115.1(4) . . ? C16 C11 C12 121.51(15) . . ? N1 C11 Cl11 8.8(5) . . ? C16 C11 Cl11 114.71(19) . . ? C12 C11 Cl11 123.78(17) . . ? C13 C12 C11 119.20(14) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 121.50(16) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 117.39(15) . . ? C15 C14 C17 119.32(13) . . ? C13 C14 C17 123.29(15) . . ? C16 C15 C14 122.15(14) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C11 C16 C15 118.26(15) . . ? C11 C16 H16A 120.9 . . ? C15 C16 H16A 120.9 . . ? C7 C17 C14 126.85(19) . . ? C7 C17 H17A 116.6 . . ? C14 C17 H17A 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 173.9(8) . . . . ? C1 Cl1 N11 O12 -172(3) . . . . ? O12 Cl1 N11 O11 -173.9(8) . . . . ? C1 Cl1 N11 O11 14(3) . . . . ? O11 Cl1 N11 C1 -14(3) . . . . ? O12 Cl1 N11 C1 172(3) . . . . ? O12 Cl1 O11 N11 134(5) . . . . ? C1 Cl1 O11 N11 -4.9(12) . . . . ? O12 N11 O11 Cl1 -7.3(10) . . . . ? C1 N11 O11 Cl1 172.6(19) . . . . ? O11 N11 O12 Cl1 4.3(6) . . . . ? C1 N11 O12 Cl1 -175.6(17) . . . . ? O11 Cl1 O12 N11 -136(5) . . . . ? C1 Cl1 O12 N11 2.7(10) . . . . ? Cl1 N11 C1 C6 12(3) . . . . ? O12 N11 C1 C6 -177.4(5) . . . . ? O11 N11 C1 C6 2.7(9) . . . . ? Cl1 N11 C1 C2 -170(3) . . . . ? O12 N11 C1 C2 1.0(8) . . . . ? O11 N11 C1 C2 -178.9(6) . . . . ? O12 N11 C1 Cl1 171(3) . . . . ? O11 N11 C1 Cl1 -9(2) . . . . ? O11 Cl1 C1 N11 168(3) . . . . ? O12 Cl1 C1 N11 -7(3) . . . . ? N11 Cl1 C1 C6 -169(3) . . . . ? O11 Cl1 C1 C6 -1.5(6) . . . . ? O12 Cl1 C1 C6 -176.40(19) . . . . ? N11 Cl1 C1 C2 11(3) . . . . ? O11 Cl1 C1 C2 178.8(5) . . . . ? O12 Cl1 C1 C2 3.9(3) . . . . ? N11 C1 C2 C3 -178.9(4) . . . . ? C6 C1 C2 C3 -0.5(2) . . . . ? Cl1 C1 C2 C3 179.25(18) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C5 -0.8(2) . . . . ? C2 C3 C4 C7 179.90(14) . . . . ? C3 C4 C5 C6 0.9(2) . . . . ? C7 C4 C5 C6 -179.75(13) . . . . ? N11 C1 C6 C5 178.9(4) . . . . ? C2 C1 C6 C5 0.6(2) . . . . ? Cl1 C1 C6 C5 -179.17(17) . . . . ? C4 C5 C6 C1 -0.8(2) . . . . ? C5 C4 C7 C17 175.76(19) . . . . ? C3 C4 C7 C17 -4.9(3) . . . . ? O1 Cl11 N1 O2 -173.9(8) . . . . ? C11 Cl11 N1 O2 172(3) . . . . ? O2 Cl11 N1 O1 173.9(8) . . . . ? C11 Cl11 N1 O1 -14(3) . . . . ? O1 Cl11 N1 C11 14(3) . . . . ? O2 Cl11 N1 C11 -172(3) . . . . ? O2 Cl11 O1 N1 -134(5) . . . . ? C11 Cl11 O1 N1 4.9(12) . . . . ? O2 N1 O1 Cl11 7.3(10) . . . . ? C11 N1 O1 Cl11 -172.6(19) . . . . ? O1 N1 O2 Cl11 -4.3(6) . . . . ? C11 N1 O2 Cl11 175.6(17) . . . . ? O1 Cl11 O2 N1 136(5) . . . . ? C11 Cl11 O2 N1 -2.7(10) . . . . ? Cl11 N1 C11 C16 -12(3) . . . . ? O2 N1 C11 C16 177.4(5) . . . . ? O1 N1 C11 C16 -2.7(9) . . . . ? Cl11 N1 C11 C12 170(3) . . . . ? O2 N1 C11 C12 -1.0(8) . . . . ? O1 N1 C11 C12 178.9(6) . . . . ? O2 N1 C11 Cl11 -171(3) . . . . ? O1 N1 C11 Cl11 9(2) . . . . ? O1 Cl11 C11 N1 -168(3) . . . . ? O2 Cl11 C11 N1 7(3) . . . . ? N1 Cl11 C11 C16 169(3) . . . . ? O1 Cl11 C11 C16 1.5(6) . . . . ? O2 Cl11 C11 C16 176.40(19) . . . . ? N1 Cl11 C11 C12 -11(3) . . . . ? O1 Cl11 C11 C12 -178.8(5) . . . . ? O2 Cl11 C11 C12 -3.9(3) . . . . ? N1 C11 C12 C13 178.9(4) . . . . ? C16 C11 C12 C13 0.5(2) . . . . ? Cl11 C11 C12 C13 -179.25(18) . . . . ? C11 C12 C13 C14 -0.6(2) . . . . ? C12 C13 C14 C15 0.8(2) . . . . ? C12 C13 C14 C17 -179.90(14) . . . . ? C13 C14 C15 C16 -0.9(2) . . . . ? C17 C14 C15 C16 179.75(13) . . . . ? N1 C11 C16 C15 -178.9(4) . . . . ? C12 C11 C16 C15 -0.6(2) . . . . ? Cl11 C11 C16 C15 179.17(17) . . . . ? C14 C15 C16 C11 0.8(2) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.76(19) . . . . ? C13 C14 C17 C7 4.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 27.75 _diffrn_measured_fraction_theta_full 0.915 _refine_diff_density_max 0.101 _refine_diff_density_min -0.088 _refine_diff_density_rms 0.023 # start Validation Reply Form _vrf_SYMMG02_CNS-DMFI-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-DMFI-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.92 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:23. ; # end Validation Reply Form #===END data_CNS-DMFII-small-P21_c _database_code_depnum_ccdc_archive 'CCDC 761231' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9220(2) _cell_length_b 12.9786(5) _cell_length_c 12.2507(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.128(2) _cell_angle_gamma 90.00 _cell_volume 622.66(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3527 _cell_measurement_theta_min 3.139 _cell_measurement_theta_max 24.334 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.659243 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3517 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 28.01 _reflns_number_total 2116 _reflns_number_gt 1286 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.0362P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2116 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1386 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3704(7) -0.46100(10) -0.1754(3) 0.1186(10) Uani 0.50 1 d P . . N11 N 0.3640(15) -0.4162(4) -0.1725(6) 0.0835(12) Uani 0.50 1 d P . . O11 O 0.3138(13) -0.4970(4) -0.1226(3) 0.1374(17) Uani 0.50 1 d P . . O12 O 0.4979(7) -0.4130(2) -0.2581(2) 0.1176(9) Uani 0.50 1 d P . . C1 C 0.2610(3) -0.32954(12) -0.12304(12) 0.0777(4) Uani 1 1 d . . . C2 C 0.3151(3) -0.23922(14) -0.17904(11) 0.0833(4) Uani 1 1 d . . . H2A H 0.4133 -0.2407 -0.2464 0.100 Uiso 1 1 calc R . . C3 C 0.2224(3) -0.14749(12) -0.13414(12) 0.0794(4) Uani 1 1 d . . . H3A H 0.2565 -0.0866 -0.1721 0.095 Uiso 1 1 calc R . . C4 C 0.0783(3) -0.14339(10) -0.03302(10) 0.0688(4) Uani 1 1 d . . . C5 C 0.0280(3) -0.23620(11) 0.02055(11) 0.0756(4) Uani 1 1 d . . . H5A H -0.0703 -0.2353 0.0879 0.091 Uiso 1 1 calc R . . C6 C 0.1191(3) -0.32926(11) -0.02306(12) 0.0806(4) Uani 1 1 d . . . H6A H 0.0854 -0.3905 0.0143 0.097 Uiso 1 1 calc R . . C7 C -0.0241(3) -0.04671(10) 0.01814(12) 0.0754(4) Uani 1 1 d . . . H7A H -0.1346 -0.0525 0.0831 0.090 Uiso 1 1 calc R . . Cl11 Cl -0.3704(7) 0.46100(10) 0.1754(3) 0.1186(10) Uani 0.50 1 d P . . N1 N -0.3640(15) 0.4162(4) 0.1725(6) 0.0835(12) Uani 0.50 1 d P . . O1 O -0.3138(13) 0.4970(4) 0.1226(3) 0.1374(17) Uani 0.50 1 d P . . O2 O -0.4979(7) 0.4130(2) 0.2581(2) 0.1176(9) Uani 0.50 1 d P . . C11 C -0.2610(3) 0.32954(12) 0.12304(12) 0.0777(4) Uani 1 1 d . . . C12 C -0.3151(3) 0.23922(14) 0.17904(11) 0.0833(4) Uani 1 1 d . . . H12A H -0.4133 0.2407 0.2464 0.100 Uiso 1 1 calc R . . C13 C -0.2224(3) 0.14749(12) 0.13414(12) 0.0794(4) Uani 1 1 d . . . H13A H -0.2565 0.0866 0.1721 0.095 Uiso 1 1 calc R . . C14 C -0.0783(3) 0.14339(10) 0.03302(10) 0.0688(4) Uani 1 1 d . . . C15 C -0.0280(3) 0.23620(11) -0.02055(11) 0.0756(4) Uani 1 1 d . . . H15A H 0.0703 0.2353 -0.0879 0.091 Uiso 1 1 calc R . . C16 C -0.1191(3) 0.32926(11) 0.02306(12) 0.0806(4) Uani 1 1 d . . . H16A H -0.0854 0.3905 -0.0143 0.097 Uiso 1 1 calc R . . C17 C 0.0241(3) 0.04671(10) -0.01814(12) 0.0754(4) Uani 1 1 d . . . H17A H 0.1346 0.0525 -0.0831 0.090 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1162(10) 0.095(2) 0.1436(18) -0.0483(19) 0.0015(11) 0.0230(14) N11 0.0770(19) 0.072(3) 0.101(3) -0.003(3) -0.0044(19) 0.006(3) O11 0.172(3) 0.079(2) 0.163(4) 0.008(2) 0.036(2) 0.0133(19) O12 0.152(2) 0.0963(18) 0.1074(18) -0.0289(15) 0.0312(16) 0.0204(15) C1 0.0611(7) 0.0883(11) 0.0829(10) -0.0143(8) -0.0041(6) 0.0052(7) C2 0.0715(8) 0.1072(13) 0.0715(9) -0.0036(8) 0.0059(7) -0.0010(8) C3 0.0729(8) 0.0845(10) 0.0808(10) 0.0074(7) 0.0038(7) -0.0034(7) C4 0.0544(6) 0.0781(9) 0.0732(9) -0.0041(7) -0.0027(6) -0.0009(6) C5 0.0719(8) 0.0824(10) 0.0728(9) 0.0024(7) 0.0053(6) 0.0002(7) C6 0.0766(8) 0.0769(10) 0.0879(10) 0.0026(7) 0.0005(7) 0.0022(7) C7 0.0644(7) 0.0841(10) 0.0777(9) 0.0043(7) 0.0039(6) -0.0027(7) Cl11 0.1162(10) 0.095(2) 0.1436(18) -0.0483(19) 0.0015(11) 0.0230(14) N1 0.0770(19) 0.072(3) 0.101(3) -0.003(3) -0.0044(19) 0.006(3) O1 0.172(3) 0.079(2) 0.163(4) 0.008(2) 0.036(2) 0.0133(19) O2 0.152(2) 0.0963(18) 0.1074(18) -0.0289(15) 0.0312(16) 0.0204(15) C11 0.0611(7) 0.0883(11) 0.0829(10) -0.0143(8) -0.0041(6) 0.0052(7) C12 0.0715(8) 0.1072(13) 0.0715(9) -0.0036(8) 0.0059(7) -0.0010(8) C13 0.0729(8) 0.0845(10) 0.0808(10) 0.0074(7) 0.0038(7) -0.0034(7) C14 0.0544(6) 0.0781(9) 0.0732(9) -0.0041(7) -0.0027(6) -0.0009(6) C15 0.0719(8) 0.0824(10) 0.0728(9) 0.0024(7) 0.0053(6) 0.0002(7) C16 0.0766(8) 0.0769(10) 0.0879(10) 0.0026(7) 0.0005(7) 0.0022(7) C17 0.0644(7) 0.0841(10) 0.0777(9) 0.0043(7) 0.0039(6) -0.0027(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.583(4) . ? Cl1 O11 0.838(4) . ? Cl1 O12 1.311(4) . ? Cl1 C1 1.880(2) . ? N11 O12 1.198(8) . ? N11 O11 1.235(9) . ? N11 C1 1.350(4) . ? C1 C6 1.373(2) . ? C1 C2 1.380(2) . ? C2 C3 1.369(2) . ? C2 H2A 0.9300 . ? C3 C4 1.3903(19) . ? C3 H3A 0.9300 . ? C4 C5 1.3910(18) . ? C4 C7 1.4682(19) . ? C5 C6 1.3759(18) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.309(2) . ? C7 H7A 0.9300 . ? Cl11 N1 0.583(4) . ? Cl11 O1 0.838(4) . ? Cl11 O2 1.311(4) . ? Cl11 C11 1.880(2) . ? N1 O2 1.198(8) . ? N1 O1 1.235(9) . ? N1 C11 1.350(4) . ? C11 C16 1.373(2) . ? C11 C12 1.380(2) . ? C12 C13 1.369(2) . ? C12 H12A 0.9300 . ? C13 C14 1.3903(19) . ? C13 H13A 0.9300 . ? C14 C15 1.3910(18) . ? C14 C17 1.4682(19) . ? C15 C16 1.3759(18) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 119.7(13) . . ? N11 Cl1 O12 66.0(10) . . ? O11 Cl1 O12 171.8(5) . . ? N11 Cl1 C1 20.5(9) . . ? O11 Cl1 C1 99.7(5) . . ? O12 Cl1 C1 86.36(15) . . ? Cl1 N11 O12 87.7(9) . . ? Cl1 N11 O11 36.1(9) . . ? O12 N11 O11 123.5(4) . . ? Cl1 N11 C1 150.8(13) . . ? O12 N11 C1 121.3(5) . . ? O11 N11 C1 115.2(5) . . ? Cl1 O11 N11 24.2(4) . . ? N11 O12 Cl1 26.4(2) . . ? N11 C1 C6 123.3(3) . . ? N11 C1 C2 115.2(3) . . ? C6 C1 C2 121.47(14) . . ? N11 C1 Cl1 8.7(4) . . ? C6 C1 Cl1 114.69(17) . . ? C2 C1 Cl1 123.83(16) . . ? C3 C2 C1 119.16(14) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.41(15) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C3 C4 C5 117.54(13) . . ? C3 C4 C7 123.16(14) . . ? C5 C4 C7 119.30(13) . . ? C6 C5 C4 122.04(13) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C1 C6 C5 118.38(14) . . ? C1 C6 H6A 120.8 . . ? C5 C6 H6A 120.8 . . ? C17 C7 C4 126.80(18) . . ? C17 C7 H7A 116.6 . . ? C4 C7 H7A 116.6 . . ? N1 Cl11 O1 119.7(13) . . ? N1 Cl11 O2 66.0(10) . . ? O1 Cl11 O2 171.8(5) . . ? N1 Cl11 C11 20.5(9) . . ? O1 Cl11 C11 99.7(5) . . ? O2 Cl11 C11 86.36(15) . . ? Cl11 N1 O2 87.7(9) . . ? Cl11 N1 O1 36.1(9) . . ? O2 N1 O1 123.5(4) . . ? Cl11 N1 C11 150.8(13) . . ? O2 N1 C11 121.3(5) . . ? O1 N1 C11 115.2(5) . . ? Cl11 O1 N1 24.2(4) . . ? N1 O2 Cl11 26.4(2) . . ? N1 C11 C16 123.3(3) . . ? N1 C11 C12 115.2(3) . . ? C16 C11 C12 121.47(14) . . ? N1 C11 Cl11 8.7(4) . . ? C16 C11 Cl11 114.69(17) . . ? C12 C11 Cl11 123.83(16) . . ? C13 C12 C11 119.16(14) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 121.41(15) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C13 C14 C15 117.54(13) . . ? C13 C14 C17 123.16(14) . . ? C15 C14 C17 119.30(13) . . ? C16 C15 C14 122.04(13) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C11 C16 C15 118.38(14) . . ? C11 C16 H16A 120.8 . . ? C15 C16 H16A 120.8 . . ? C7 C17 C14 126.80(18) . . ? C7 C17 H17A 116.6 . . ? C14 C17 H17A 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 173.4(6) . . . . ? C1 Cl1 N11 O12 -174(2) . . . . ? O12 Cl1 N11 O11 -173.4(6) . . . . ? C1 Cl1 N11 O11 13(3) . . . . ? O11 Cl1 N11 C1 -13(3) . . . . ? O12 Cl1 N11 C1 174(2) . . . . ? O12 Cl1 O11 N11 132(4) . . . . ? C1 Cl1 O11 N11 -4.6(9) . . . . ? O12 N11 O11 Cl1 -7.9(8) . . . . ? C1 N11 O11 Cl1 173.0(14) . . . . ? O11 N11 O12 Cl1 4.7(5) . . . . ? C1 N11 O12 Cl1 -176.3(13) . . . . ? O11 Cl1 O12 N11 -135(4) . . . . ? C1 Cl1 O12 N11 2.3(8) . . . . ? Cl1 N11 C1 C6 10(2) . . . . ? O12 N11 C1 C6 -177.3(4) . . . . ? O11 N11 C1 C6 1.8(7) . . . . ? Cl1 N11 C1 C2 -171(2) . . . . ? O12 N11 C1 C2 1.3(6) . . . . ? O11 N11 C1 C2 -179.6(5) . . . . ? O12 N11 C1 Cl1 172(3) . . . . ? O11 N11 C1 Cl1 -8.5(18) . . . . ? O11 Cl1 C1 N11 168(2) . . . . ? O12 Cl1 C1 N11 -6(2) . . . . ? N11 Cl1 C1 C6 -171(2) . . . . ? O11 Cl1 C1 C6 -2.1(5) . . . . ? O12 Cl1 C1 C6 -176.48(17) . . . . ? N11 Cl1 C1 C2 10(2) . . . . ? O11 Cl1 C1 C2 178.1(4) . . . . ? O12 Cl1 C1 C2 3.7(2) . . . . ? N11 C1 C2 C3 -179.2(3) . . . . ? C6 C1 C2 C3 -0.6(2) . . . . ? Cl1 C1 C2 C3 179.24(14) . . . . ? C1 C2 C3 C4 0.7(2) . . . . ? C2 C3 C4 C5 -0.71(19) . . . . ? C2 C3 C4 C7 179.88(12) . . . . ? C3 C4 C5 C6 0.69(19) . . . . ? C7 C4 C5 C6 -179.88(12) . . . . ? N11 C1 C6 C5 179.0(3) . . . . ? C2 C1 C6 C5 0.5(2) . . . . ? Cl1 C1 C6 C5 -179.29(14) . . . . ? C4 C5 C6 C1 -0.6(2) . . . . ? C3 C4 C7 C17 -5.0(3) . . . . ? C5 C4 C7 C17 175.63(16) . . . . ? O1 Cl11 N1 O2 -173.4(6) . . . . ? C11 Cl11 N1 O2 174(2) . . . . ? O2 Cl11 N1 O1 173.4(6) . . . . ? C11 Cl11 N1 O1 -13(3) . . . . ? O1 Cl11 N1 C11 13(3) . . . . ? O2 Cl11 N1 C11 -174(2) . . . . ? O2 Cl11 O1 N1 -132(4) . . . . ? C11 Cl11 O1 N1 4.6(9) . . . . ? O2 N1 O1 Cl11 7.9(8) . . . . ? C11 N1 O1 Cl11 -173.0(14) . . . . ? O1 N1 O2 Cl11 -4.7(5) . . . . ? C11 N1 O2 Cl11 176.3(13) . . . . ? O1 Cl11 O2 N1 135(4) . . . . ? C11 Cl11 O2 N1 -2.3(8) . . . . ? Cl11 N1 C11 C16 -10(2) . . . . ? O2 N1 C11 C16 177.3(4) . . . . ? O1 N1 C11 C16 -1.8(7) . . . . ? Cl11 N1 C11 C12 171(2) . . . . ? O2 N1 C11 C12 -1.3(6) . . . . ? O1 N1 C11 C12 179.6(5) . . . . ? O2 N1 C11 Cl11 -172(3) . . . . ? O1 N1 C11 Cl11 8.5(18) . . . . ? O1 Cl11 C11 N1 -168(2) . . . . ? O2 Cl11 C11 N1 6(2) . . . . ? N1 Cl11 C11 C16 171(2) . . . . ? O1 Cl11 C11 C16 2.1(5) . . . . ? O2 Cl11 C11 C16 176.48(17) . . . . ? N1 Cl11 C11 C12 -10(2) . . . . ? O1 Cl11 C11 C12 -178.1(4) . . . . ? O2 Cl11 C11 C12 -3.7(2) . . . . ? N1 C11 C12 C13 179.2(3) . . . . ? C16 C11 C12 C13 0.6(2) . . . . ? Cl11 C11 C12 C13 -179.24(14) . . . . ? C11 C12 C13 C14 -0.7(2) . . . . ? C12 C13 C14 C15 0.71(19) . . . . ? C12 C13 C14 C17 -179.88(12) . . . . ? C13 C14 C15 C16 -0.69(19) . . . . ? C17 C14 C15 C16 179.88(12) . . . . ? N1 C11 C16 C15 -179.0(3) . . . . ? C12 C11 C16 C15 -0.5(2) . . . . ? Cl11 C11 C16 C15 179.29(14) . . . . ? C14 C15 C16 C11 0.6(2) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 5.0(3) . . . . ? C15 C14 C17 C7 -175.63(16) . . . . ? _diffrn_measured_fraction_theta_max 0.872 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.872 _refine_diff_density_max 0.107 _refine_diff_density_min -0.111 _refine_diff_density_rms 0.028 # start Validation Reply Form _vrf_SYMMG02_CNS-DMFII-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-DMFII-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.87 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:21. ; # end Validation Reply Form #===END data_CNS-DMFII-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761232' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9220(2) _cell_length_b 12.9786(5) _cell_length_c 12.2507(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.128(2) _cell_angle_gamma 90.00 _cell_volume 622.66(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3527 _cell_measurement_theta_min 3.139 _cell_measurement_theta_max 24.334 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.659243 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3517 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 28.01 _reflns_number_total 2116 _reflns_number_gt 1286 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.0362P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_number_reflns 2116 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1324 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3705(7) -0.46097(10) -0.1754(3) 0.1184(9) Uani 0.455(2) 1 d P . . N11 N 0.3644(14) -0.4162(3) -0.1725(5) 0.0841(12) Uani 0.545(2) 1 d P . . O11 O 0.3135(12) -0.4969(3) -0.1227(3) 0.1367(16) Uani 0.545(2) 1 d P . . O12 O 0.4980(7) -0.41308(19) -0.2581(2) 0.1169(8) Uani 0.545(2) 1 d P . . C1 C 0.2611(3) -0.32954(12) -0.12307(12) 0.0778(4) Uani 1 1 d . . . C2 C 0.3151(3) -0.23915(13) -0.17916(11) 0.0831(4) Uani 1 1 d . . . H2A H 0.4132 -0.2406 -0.2466 0.100 Uiso 1 1 calc R . . C3 C 0.2223(3) -0.14752(11) -0.13413(11) 0.0796(4) Uani 1 1 d . . . H3A H 0.2564 -0.0866 -0.1721 0.095 Uiso 1 1 calc R . . C4 C 0.0783(3) -0.14333(10) -0.03306(10) 0.0686(4) Uani 1 1 d . . . C5 C 0.0280(3) -0.23622(10) 0.02055(11) 0.0757(4) Uani 1 1 d . . . H5A H -0.0703 -0.2353 0.0879 0.091 Uiso 1 1 calc R . . C6 C 0.1192(3) -0.32922(10) -0.02300(12) 0.0804(4) Uani 1 1 d . . . H6A H 0.0856 -0.3904 0.0144 0.096 Uiso 1 1 calc R . . C7 C -0.0240(3) -0.04673(9) 0.01808(11) 0.0753(4) Uani 1 1 d . . . H7A H -0.1346 -0.0525 0.0830 0.090 Uiso 1 1 calc R . . Cl11 Cl -0.3705(7) 0.46097(10) 0.1754(3) 0.1184(9) Uani 0.545(2) 1 d P . . N1 N -0.3644(14) 0.4162(3) 0.1725(5) 0.0841(12) Uani 0.455(2) 1 d P . . O1 O -0.3135(12) 0.4969(3) 0.1227(3) 0.1367(16) Uani 0.455(2) 1 d P . . O2 O -0.4980(7) 0.41308(19) 0.2581(2) 0.1169(8) Uani 0.455(2) 1 d P . . C11 C -0.2611(3) 0.32954(12) 0.12307(12) 0.0778(4) Uani 1 1 d . . . C12 C -0.3151(3) 0.23915(13) 0.17916(11) 0.0831(4) Uani 1 1 d . . . H12A H -0.4132 0.2406 0.2466 0.100 Uiso 1 1 calc R . . C13 C -0.2223(3) 0.14752(11) 0.13413(11) 0.0796(4) Uani 1 1 d . . . H13A H -0.2564 0.0866 0.1721 0.095 Uiso 1 1 calc R . . C14 C -0.0783(3) 0.14333(10) 0.03306(10) 0.0686(4) Uani 1 1 d . . . C15 C -0.0280(3) 0.23622(10) -0.02055(11) 0.0757(4) Uani 1 1 d . . . H15A H 0.0703 0.2353 -0.0879 0.091 Uiso 1 1 calc R . . C16 C -0.1192(3) 0.32922(10) 0.02300(12) 0.0804(4) Uani 1 1 d . . . H16A H -0.0856 0.3904 -0.0144 0.096 Uiso 1 1 calc R . . C17 C 0.0240(3) 0.04673(9) -0.01808(11) 0.0753(4) Uani 1 1 d . . . H17A H 0.1346 0.0525 -0.0830 0.090 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1157(10) 0.0954(18) 0.1436(17) -0.0484(18) 0.0016(10) 0.0226(13) N11 0.0774(19) 0.072(3) 0.102(3) -0.004(3) -0.0056(19) 0.006(2) O11 0.170(3) 0.079(2) 0.163(4) 0.008(2) 0.037(2) 0.0131(18) O12 0.152(2) 0.0956(17) 0.1059(17) -0.0276(14) 0.0327(16) 0.0200(14) C1 0.0607(7) 0.0888(11) 0.0831(9) -0.0142(8) -0.0044(6) 0.0053(6) C2 0.0713(8) 0.1067(12) 0.0715(9) -0.0035(7) 0.0062(6) -0.0007(7) C3 0.0726(8) 0.0848(10) 0.0811(9) 0.0079(7) 0.0033(6) -0.0035(6) C4 0.0544(6) 0.0783(9) 0.0725(8) -0.0041(6) -0.0026(5) -0.0009(5) C5 0.0716(7) 0.0828(10) 0.0729(8) 0.0026(7) 0.0054(6) 0.0004(7) C6 0.0766(8) 0.0767(10) 0.0874(10) 0.0026(7) 0.0009(7) 0.0020(7) C7 0.0642(7) 0.0839(10) 0.0776(8) 0.0042(7) 0.0037(6) -0.0026(6) Cl11 0.1157(10) 0.0954(18) 0.1436(17) -0.0484(18) 0.0016(10) 0.0226(13) N1 0.0774(19) 0.072(3) 0.102(3) -0.004(3) -0.0056(19) 0.006(2) O1 0.170(3) 0.079(2) 0.163(4) 0.008(2) 0.037(2) 0.0131(18) O2 0.152(2) 0.0956(17) 0.1059(17) -0.0276(14) 0.0327(16) 0.0200(14) C11 0.0607(7) 0.0888(11) 0.0831(9) -0.0142(8) -0.0044(6) 0.0053(6) C12 0.0713(8) 0.1067(12) 0.0715(9) -0.0035(7) 0.0062(6) -0.0007(7) C13 0.0726(8) 0.0848(10) 0.0811(9) 0.0079(7) 0.0033(6) -0.0035(6) C14 0.0544(6) 0.0783(9) 0.0725(8) -0.0041(6) -0.0026(5) -0.0009(5) C15 0.0716(7) 0.0828(10) 0.0729(8) 0.0026(7) 0.0054(6) 0.0004(7) C16 0.0766(8) 0.0767(10) 0.0874(10) 0.0026(7) 0.0009(7) 0.0020(7) C17 0.0642(7) 0.0839(10) 0.0776(8) 0.0042(7) 0.0037(6) -0.0026(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.583(4) . ? Cl1 O11 0.837(3) . ? Cl1 O12 1.310(4) . ? Cl1 C1 1.8803(19) . ? N11 O12 1.198(7) . ? N11 O11 1.234(8) . ? N11 C1 1.350(4) . ? C1 C6 1.374(2) . ? C1 C2 1.382(2) . ? C2 C3 1.369(2) . ? C2 H2A 0.9300 . ? C3 C4 1.3896(18) . ? C3 H3A 0.9300 . ? C4 C5 1.3920(17) . ? C4 C7 1.4672(18) . ? C5 C6 1.3748(17) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.309(2) . ? C7 H7A 0.9300 . ? Cl11 N1 0.583(4) . ? Cl11 O1 0.837(3) . ? Cl11 O2 1.310(4) . ? Cl11 C11 1.8803(19) . ? N1 O2 1.198(7) . ? N1 O1 1.234(8) . ? N1 C11 1.350(4) . ? C11 C16 1.374(2) . ? C11 C12 1.382(2) . ? C12 C13 1.369(2) . ? C12 H12A 0.9300 . ? C13 C14 1.3896(18) . ? C13 H13A 0.9300 . ? C14 C15 1.3920(17) . ? C14 C17 1.4672(18) . ? C15 C16 1.3748(17) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 119.6(12) . . ? N11 Cl1 O12 66.0(9) . . ? O11 Cl1 O12 171.9(5) . . ? N11 Cl1 C1 20.5(8) . . ? O11 Cl1 C1 99.6(5) . . ? O12 Cl1 C1 86.39(14) . . ? Cl1 N11 O12 87.6(9) . . ? Cl1 N11 O11 36.1(8) . . ? O12 N11 O11 123.4(4) . . ? Cl1 N11 C1 150.8(12) . . ? O12 N11 C1 121.4(5) . . ? O11 N11 C1 115.2(5) . . ? Cl1 O11 N11 24.3(4) . . ? N11 O12 Cl1 26.4(2) . . ? N11 C1 C6 123.3(3) . . ? N11 C1 C2 115.2(3) . . ? C6 C1 C2 121.46(13) . . ? N11 C1 Cl1 8.7(4) . . ? C6 C1 Cl1 114.72(16) . . ? C2 C1 Cl1 123.82(15) . . ? C3 C2 C1 119.07(13) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 121.54(14) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 117.48(13) . . ? C3 C4 C7 123.22(13) . . ? C5 C4 C7 119.31(12) . . ? C6 C5 C4 122.06(13) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C1 C6 C5 118.39(13) . . ? C1 C6 H6A 120.8 . . ? C5 C6 H6A 120.8 . . ? C17 C7 C4 126.86(17) . . ? C17 C7 H7A 116.6 . . ? C4 C7 H7A 116.6 . . ? N1 Cl11 O1 119.6(12) . . ? N1 Cl11 O2 66.0(9) . . ? O1 Cl11 O2 171.9(5) . . ? N1 Cl11 C11 20.5(8) . . ? O1 Cl11 C11 99.6(5) . . ? O2 Cl11 C11 86.39(14) . . ? Cl11 N1 O2 87.6(9) . . ? Cl11 N1 O1 36.1(8) . . ? O2 N1 O1 123.4(4) . . ? Cl11 N1 C11 150.8(12) . . ? O2 N1 C11 121.4(5) . . ? O1 N1 C11 115.2(5) . . ? Cl11 O1 N1 24.3(4) . . ? N1 O2 Cl11 26.4(2) . . ? N1 C11 C16 123.3(3) . . ? N1 C11 C12 115.2(3) . . ? C16 C11 C12 121.46(13) . . ? N1 C11 Cl11 8.7(4) . . ? C16 C11 Cl11 114.72(16) . . ? C12 C11 Cl11 123.82(15) . . ? C13 C12 C11 119.07(13) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C14 121.54(14) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C13 C14 C15 117.48(13) . . ? C13 C14 C17 123.22(13) . . ? C15 C14 C17 119.31(12) . . ? C16 C15 C14 122.06(13) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C11 C16 C15 118.39(13) . . ? C11 C16 H16A 120.8 . . ? C15 C16 H16A 120.8 . . ? C7 C17 C14 126.86(17) . . ? C7 C17 H17A 116.6 . . ? C14 C17 H17A 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 173.4(6) . . . . ? C1 Cl1 N11 O12 -173(2) . . . . ? O12 Cl1 N11 O11 -173.4(6) . . . . ? C1 Cl1 N11 O11 14(3) . . . . ? O11 Cl1 N11 C1 -14(3) . . . . ? O12 Cl1 N11 C1 173(2) . . . . ? O12 Cl1 O11 N11 132(4) . . . . ? C1 Cl1 O11 N11 -4.8(9) . . . . ? O12 N11 O11 Cl1 -7.9(7) . . . . ? C1 N11 O11 Cl1 172.7(14) . . . . ? O11 N11 O12 Cl1 4.6(4) . . . . ? C1 N11 O12 Cl1 -176.0(12) . . . . ? O11 Cl1 O12 N11 -135(4) . . . . ? C1 Cl1 O12 N11 2.4(8) . . . . ? Cl1 N11 C1 C6 11(2) . . . . ? O12 N11 C1 C6 -177.4(4) . . . . ? O11 N11 C1 C6 2.0(7) . . . . ? Cl1 N11 C1 C2 -171(2) . . . . ? O12 N11 C1 C2 1.2(6) . . . . ? O11 N11 C1 C2 -179.5(4) . . . . ? O12 N11 C1 Cl1 172(3) . . . . ? O11 N11 C1 Cl1 -8.8(17) . . . . ? O11 Cl1 C1 N11 168(2) . . . . ? O12 Cl1 C1 N11 -6(2) . . . . ? N11 Cl1 C1 C6 -170(2) . . . . ? O11 Cl1 C1 C6 -2.0(5) . . . . ? O12 Cl1 C1 C6 -176.45(16) . . . . ? N11 Cl1 C1 C2 10(2) . . . . ? O11 Cl1 C1 C2 178.2(4) . . . . ? O12 Cl1 C1 C2 3.8(2) . . . . ? N11 C1 C2 C3 -179.1(3) . . . . ? C6 C1 C2 C3 -0.5(2) . . . . ? Cl1 C1 C2 C3 179.22(14) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C5 -0.69(19) . . . . ? C2 C3 C4 C7 179.88(11) . . . . ? C3 C4 C5 C6 0.70(18) . . . . ? C7 C4 C5 C6 -179.85(11) . . . . ? N11 C1 C6 C5 179.0(3) . . . . ? C2 C1 C6 C5 0.5(2) . . . . ? Cl1 C1 C6 C5 -179.24(13) . . . . ? C4 C5 C6 C1 -0.62(19) . . . . ? C3 C4 C7 C17 -5.0(2) . . . . ? C5 C4 C7 C17 175.60(16) . . . . ? O1 Cl11 N1 O2 -173.4(6) . . . . ? C11 Cl11 N1 O2 173(2) . . . . ? O2 Cl11 N1 O1 173.4(6) . . . . ? C11 Cl11 N1 O1 -14(3) . . . . ? O1 Cl11 N1 C11 14(3) . . . . ? O2 Cl11 N1 C11 -173(2) . . . . ? O2 Cl11 O1 N1 -132(4) . . . . ? C11 Cl11 O1 N1 4.8(9) . . . . ? O2 N1 O1 Cl11 7.9(7) . . . . ? C11 N1 O1 Cl11 -172.7(14) . . . . ? O1 N1 O2 Cl11 -4.6(4) . . . . ? C11 N1 O2 Cl11 176.0(12) . . . . ? O1 Cl11 O2 N1 135(4) . . . . ? C11 Cl11 O2 N1 -2.4(8) . . . . ? Cl11 N1 C11 C16 -11(2) . . . . ? O2 N1 C11 C16 177.4(4) . . . . ? O1 N1 C11 C16 -2.0(7) . . . . ? Cl11 N1 C11 C12 171(2) . . . . ? O2 N1 C11 C12 -1.2(6) . . . . ? O1 N1 C11 C12 179.5(4) . . . . ? O2 N1 C11 Cl11 -172(3) . . . . ? O1 N1 C11 Cl11 8.8(17) . . . . ? O1 Cl11 C11 N1 -168(2) . . . . ? O2 Cl11 C11 N1 6(2) . . . . ? N1 Cl11 C11 C16 170(2) . . . . ? O1 Cl11 C11 C16 2.0(5) . . . . ? O2 Cl11 C11 C16 176.45(16) . . . . ? N1 Cl11 C11 C12 -10(2) . . . . ? O1 Cl11 C11 C12 -178.2(4) . . . . ? O2 Cl11 C11 C12 -3.8(2) . . . . ? N1 C11 C12 C13 179.1(3) . . . . ? C16 C11 C12 C13 0.5(2) . . . . ? Cl11 C11 C12 C13 -179.22(14) . . . . ? C11 C12 C13 C14 -0.6(2) . . . . ? C12 C13 C14 C15 0.69(19) . . . . ? C12 C13 C14 C17 -179.88(11) . . . . ? C13 C14 C15 C16 -0.70(18) . . . . ? C17 C14 C15 C16 179.85(11) . . . . ? N1 C11 C16 C15 -179.0(3) . . . . ? C12 C11 C16 C15 -0.5(2) . . . . ? Cl11 C11 C16 C15 179.24(13) . . . . ? C14 C15 C16 C11 0.62(19) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C13 C14 C17 C7 5.0(2) . . . . ? C15 C14 C17 C7 -175.60(16) . . . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.910 _refine_diff_density_max 0.112 _refine_diff_density_min -0.116 _refine_diff_density_rms 0.028 # start Validation Reply Form _vrf_SYMMG02_CNS-DMFII-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-DMFII-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.91 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:21. ; # end Validation Reply Form #===END data_CNS-DMSOI-small-P21/c _database_code_depnum_ccdc_archive 'CCDC 761233' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall 'P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.91920(10) _cell_length_b 12.9630(4) _cell_length_c 12.2399(4) _cell_angle_alpha 90.000(2) _cell_angle_beta 93.188(2) _cell_angle_gamma 90.000(2) _cell_volume 620.88(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3483 _cell_measurement_theta_min 3.143 _cell_measurement_theta_max 26.239 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.812887 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3467 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.80 _reflns_number_total 1974 _reflns_number_gt 1393 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.0577P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.023(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 1974 _refine_ls_number_parameters 102 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1107 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3704(6) -0.46097(9) -0.1753(2) 0.1122(8) Uani 0.50 1 d P . . N11 N 0.3629(14) -0.4150(3) -0.1727(5) 0.0825(11) Uani 0.50 1 d P . . O11 O 0.3161(11) -0.4979(3) -0.1232(3) 0.1303(14) Uani 0.50 1 d P . . O12 O 0.4982(7) -0.41278(19) -0.25804(19) 0.1138(8) Uani 0.50 1 d P . . C1 C 0.2614(3) -0.32958(11) -0.12301(11) 0.0746(4) Uani 1 1 d . . . C2 C 0.3146(3) -0.23924(13) -0.17914(10) 0.0806(4) Uani 1 1 d . . . H2A H 0.4118 -0.2407 -0.2467 0.097 Uiso 1 1 calc R . . C3 C 0.2228(3) -0.14750(11) -0.13422(10) 0.0764(4) Uani 1 1 d . . . H3A H 0.2577 -0.0866 -0.1721 0.092 Uiso 1 1 calc R . . C4 C 0.0781(3) -0.14334(10) -0.03283(9) 0.0659(3) Uani 1 1 d . . . C5 C 0.0283(3) -0.23615(11) 0.02061(10) 0.0728(4) Uani 1 1 d . . . H5A H -0.0698 -0.2352 0.0881 0.087 Uiso 1 1 calc R . . C6 C 0.1187(3) -0.32922(11) -0.02266(10) 0.0770(4) Uani 1 1 d . . . H6A H 0.0846 -0.3905 0.0148 0.092 Uiso 1 1 calc R . . C7 C -0.0243(3) -0.04660(9) 0.01844(10) 0.0722(4) Uani 1 1 d . . . H7A H -0.1346 -0.0522 0.0835 0.087 Uiso 1 1 calc R . . Cl11 Cl -0.3704(6) 0.46097(9) 0.1753(2) 0.1122(8) Uani 0.50 1 d P . . N1 N -0.3629(14) 0.4150(3) 0.1727(5) 0.0825(11) Uani 0.50 1 d P . . O1 O -0.3161(11) 0.4979(3) 0.1232(3) 0.1303(14) Uani 0.50 1 d P . . O2 O -0.4982(7) 0.41278(19) 0.25804(19) 0.1138(8) Uani 0.50 1 d P . . C11 C -0.2614(3) 0.32958(11) 0.12301(11) 0.0746(4) Uani 1 1 d . . . C12 C -0.3146(3) 0.23924(13) 0.17914(10) 0.0806(4) Uani 1 1 d . . . H12A H -0.4118 0.2407 0.2467 0.097 Uiso 1 1 calc R . . C13 C -0.2228(3) 0.14750(11) 0.13422(10) 0.0764(4) Uani 1 1 d . . . H13A H -0.2577 0.0866 0.1721 0.092 Uiso 1 1 calc R . . C14 C -0.0781(3) 0.14334(10) 0.03283(9) 0.0659(3) Uani 1 1 d . . . C15 C -0.0283(3) 0.23615(11) -0.02061(10) 0.0728(4) Uani 1 1 d . . . H15A H 0.0698 0.2352 -0.0881 0.087 Uiso 1 1 calc R . . C16 C -0.1187(3) 0.32922(11) 0.02266(10) 0.0770(4) Uani 1 1 d . . . H16A H -0.0846 0.3905 -0.0148 0.092 Uiso 1 1 calc R . . C17 C 0.0243(3) 0.04660(9) -0.01844(10) 0.0722(4) Uani 1 1 d . . . H17A H 0.1346 0.0522 -0.0835 0.087 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1124(9) 0.0913(16) 0.1326(14) -0.0437(15) 0.0044(9) 0.0234(12) N11 0.0802(19) 0.066(3) 0.100(3) -0.002(2) -0.0031(17) 0.007(2) O11 0.171(3) 0.077(2) 0.147(3) 0.0117(18) 0.040(2) 0.0133(18) O12 0.150(2) 0.0941(17) 0.0998(15) -0.0267(14) 0.0322(14) 0.0196(14) C1 0.0591(7) 0.0877(10) 0.0765(8) -0.0148(7) -0.0013(5) 0.0059(6) C2 0.0697(8) 0.1069(12) 0.0658(8) -0.0031(7) 0.0089(6) -0.0006(7) C3 0.0702(7) 0.0853(10) 0.0742(8) 0.0075(7) 0.0070(6) -0.0034(7) C4 0.0522(6) 0.0786(9) 0.0668(7) -0.0033(6) 0.0008(5) -0.0012(5) C5 0.0693(7) 0.0833(10) 0.0663(7) 0.0019(6) 0.0083(5) -0.0003(7) C6 0.0733(8) 0.0785(9) 0.0792(8) 0.0024(7) 0.0048(6) 0.0018(7) C7 0.0617(7) 0.0841(10) 0.0712(7) 0.0040(6) 0.0066(5) -0.0030(7) Cl11 0.1124(9) 0.0913(16) 0.1326(14) -0.0437(15) 0.0044(9) 0.0234(12) N1 0.0802(19) 0.066(3) 0.100(3) -0.002(2) -0.0031(17) 0.007(2) O1 0.171(3) 0.077(2) 0.147(3) 0.0117(18) 0.040(2) 0.0133(18) O2 0.150(2) 0.0941(17) 0.0998(15) -0.0267(14) 0.0322(14) 0.0196(14) C11 0.0591(7) 0.0877(10) 0.0765(8) -0.0148(7) -0.0013(5) 0.0059(6) C12 0.0697(8) 0.1069(12) 0.0658(8) -0.0031(7) 0.0089(6) -0.0006(7) C13 0.0702(7) 0.0853(10) 0.0742(8) 0.0075(7) 0.0070(6) -0.0034(7) C14 0.0522(6) 0.0786(9) 0.0668(7) -0.0033(6) 0.0008(5) -0.0012(5) C15 0.0693(7) 0.0833(10) 0.0663(7) 0.0019(6) 0.0083(5) -0.0003(7) C16 0.0733(8) 0.0785(9) 0.0792(8) 0.0024(7) 0.0048(6) 0.0018(7) C17 0.0617(7) 0.0841(10) 0.0712(7) 0.0040(6) 0.0066(5) -0.0030(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.598(4) . ? Cl1 O11 0.835(3) . ? Cl1 O12 1.312(3) . ? Cl1 C1 1.8773(18) . ? N11 O12 1.197(6) . ? N11 O11 1.253(7) . ? N11 C1 1.335(4) . ? C1 C6 1.3776(19) . ? C1 C2 1.3794(19) . ? C2 C3 1.367(2) . ? C2 H2A 0.9300 . ? C3 C4 1.3940(18) . ? C3 H3A 0.9300 . ? C4 C5 1.3884(17) . ? C4 C7 1.4682(18) . ? C5 C6 1.3720(17) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.307(2) . ? C7 H7A 0.9300 . ? Cl11 N1 0.598(4) . ? Cl11 O1 0.835(3) . ? Cl11 O2 1.312(3) . ? Cl11 C11 1.8773(18) . ? N1 O2 1.197(6) . ? N1 O1 1.253(7) . ? N1 C11 1.335(4) . ? C11 C16 1.3776(19) . ? C11 C12 1.3794(19) . ? C12 C13 1.367(2) . ? C12 H12A 0.9300 . ? C13 C14 1.3940(18) . ? C13 H13A 0.9300 . ? C14 C15 1.3884(17) . ? C14 C17 1.4682(18) . ? C15 C16 1.3720(17) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 121.1(10) . . ? N11 Cl1 O12 65.7(8) . . ? O11 Cl1 O12 170.8(4) . . ? N11 Cl1 C1 20.6(7) . . ? O11 Cl1 C1 100.8(4) . . ? O12 Cl1 C1 86.28(14) . . ? Cl1 N11 O12 87.2(7) . . ? Cl1 N11 O11 34.8(7) . . ? O12 N11 O11 121.8(4) . . ? Cl1 N11 C1 150.3(10) . . ? O12 N11 C1 122.4(4) . . ? O11 N11 C1 115.9(4) . . ? Cl1 O11 N11 24.1(3) . . ? N11 O12 Cl1 27.06(18) . . ? N11 C1 C6 123.7(3) . . ? N11 C1 C2 114.8(3) . . ? C6 C1 C2 121.42(13) . . ? N11 C1 Cl1 9.1(3) . . ? C6 C1 Cl1 114.75(15) . . ? C2 C1 Cl1 123.83(13) . . ? C3 C2 C1 119.20(12) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.40(14) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.44(13) . . ? C5 C4 C7 119.33(11) . . ? C3 C4 C7 123.23(13) . . ? C6 C5 C4 122.27(12) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C5 C6 C1 118.26(13) . . ? C5 C6 H6A 120.9 . . ? C1 C6 H6A 120.9 . . ? C17 C7 C4 126.38(16) . . ? C17 C7 H7A 116.8 . . ? C4 C7 H7A 116.8 . . ? N1 Cl11 O1 121.1(10) . . ? N1 Cl11 O2 65.7(8) . . ? O1 Cl11 O2 170.8(4) . . ? N1 Cl11 C11 20.6(7) . . ? O1 Cl11 C11 100.8(4) . . ? O2 Cl11 C11 86.28(14) . . ? Cl11 N1 O2 87.2(7) . . ? Cl11 N1 O1 34.8(7) . . ? O2 N1 O1 121.8(4) . . ? Cl11 N1 C11 150.3(10) . . ? O2 N1 C11 122.4(4) . . ? O1 N1 C11 115.9(4) . . ? Cl11 O1 N1 24.1(3) . . ? N1 O2 Cl11 27.06(18) . . ? N1 C11 C16 123.7(3) . . ? N1 C11 C12 114.8(3) . . ? C16 C11 C12 121.42(13) . . ? N1 C11 Cl11 9.1(3) . . ? C16 C11 Cl11 114.75(15) . . ? C12 C11 Cl11 123.83(13) . . ? C13 C12 C11 119.20(12) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 121.40(14) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 117.44(13) . . ? C15 C14 C17 119.33(11) . . ? C13 C14 C17 123.23(13) . . ? C16 C15 C14 122.27(12) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C15 C16 C11 118.26(13) . . ? C15 C16 H16A 120.9 . . ? C11 C16 H16A 120.9 . . ? C7 C17 C14 126.38(16) . . ? C7 C17 H17A 116.8 . . ? C14 C17 H17A 116.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.9(6) . . . . ? C1 Cl1 N11 O12 -175(2) . . . . ? O12 Cl1 N11 O11 -172.9(6) . . . . ? C1 Cl1 N11 O11 12(2) . . . . ? O11 Cl1 N11 C1 -12(2) . . . . ? O12 Cl1 N11 C1 175(2) . . . . ? O12 Cl1 O11 N11 136(3) . . . . ? C1 Cl1 O11 N11 -4.2(8) . . . . ? O12 N11 O11 Cl1 -8.3(7) . . . . ? C1 N11 O11 Cl1 173.5(13) . . . . ? O11 N11 O12 Cl1 4.7(4) . . . . ? C1 N11 O12 Cl1 -177.2(12) . . . . ? O11 Cl1 O12 N11 -139(3) . . . . ? C1 Cl1 O12 N11 1.7(7) . . . . ? Cl1 N11 C1 C6 9(2) . . . . ? O12 N11 C1 C6 -177.1(4) . . . . ? O11 N11 C1 C6 1.2(7) . . . . ? Cl1 N11 C1 C2 -172.3(18) . . . . ? O12 N11 C1 C2 1.9(6) . . . . ? O11 N11 C1 C2 -179.8(4) . . . . ? O12 N11 C1 Cl1 174(2) . . . . ? O11 N11 C1 Cl1 -7.5(15) . . . . ? O11 Cl1 C1 N11 170(2) . . . . ? O12 Cl1 C1 N11 -4.4(18) . . . . ? N11 Cl1 C1 C6 -172.1(19) . . . . ? O11 Cl1 C1 C6 -2.4(4) . . . . ? O12 Cl1 C1 C6 -176.49(15) . . . . ? N11 Cl1 C1 C2 8(2) . . . . ? O11 Cl1 C1 C2 178.0(4) . . . . ? O12 Cl1 C1 C2 4.0(2) . . . . ? N11 C1 C2 C3 -179.2(3) . . . . ? C6 C1 C2 C3 -0.19(19) . . . . ? Cl1 C1 C2 C3 179.32(13) . . . . ? C1 C2 C3 C4 0.28(19) . . . . ? C2 C3 C4 C5 -0.46(18) . . . . ? C2 C3 C4 C7 -179.98(11) . . . . ? C3 C4 C5 C6 0.57(17) . . . . ? C7 C4 C5 C6 -179.89(11) . . . . ? C4 C5 C6 C1 -0.49(18) . . . . ? N11 C1 C6 C5 179.2(3) . . . . ? C2 C1 C6 C5 0.29(19) . . . . ? Cl1 C1 C6 C5 -179.27(12) . . . . ? C5 C4 C7 C17 175.69(15) . . . . ? C3 C4 C7 C17 -4.8(2) . . . . ? O1 Cl11 N1 O2 -172.9(6) . . . . ? C11 Cl11 N1 O2 175(2) . . . . ? O2 Cl11 N1 O1 172.9(6) . . . . ? C11 Cl11 N1 O1 -12(2) . . . . ? O1 Cl11 N1 C11 12(2) . . . . ? O2 Cl11 N1 C11 -175(2) . . . . ? O2 Cl11 O1 N1 -136(3) . . . . ? C11 Cl11 O1 N1 4.2(8) . . . . ? O2 N1 O1 Cl11 8.3(7) . . . . ? C11 N1 O1 Cl11 -173.5(13) . . . . ? O1 N1 O2 Cl11 -4.7(4) . . . . ? C11 N1 O2 Cl11 177.2(12) . . . . ? O1 Cl11 O2 N1 139(3) . . . . ? C11 Cl11 O2 N1 -1.7(7) . . . . ? Cl11 N1 C11 C16 -9(2) . . . . ? O2 N1 C11 C16 177.1(4) . . . . ? O1 N1 C11 C16 -1.2(7) . . . . ? Cl11 N1 C11 C12 172.3(18) . . . . ? O2 N1 C11 C12 -1.9(6) . . . . ? O1 N1 C11 C12 179.8(4) . . . . ? O2 N1 C11 Cl11 -174(2) . . . . ? O1 N1 C11 Cl11 7.5(15) . . . . ? O1 Cl11 C11 N1 -170(2) . . . . ? O2 Cl11 C11 N1 4.4(18) . . . . ? N1 Cl11 C11 C16 172.1(19) . . . . ? O1 Cl11 C11 C16 2.4(4) . . . . ? O2 Cl11 C11 C16 176.49(15) . . . . ? N1 Cl11 C11 C12 -8(2) . . . . ? O1 Cl11 C11 C12 -178.0(4) . . . . ? O2 Cl11 C11 C12 -4.0(2) . . . . ? N1 C11 C12 C13 179.2(3) . . . . ? C16 C11 C12 C13 0.19(19) . . . . ? Cl11 C11 C12 C13 -179.32(13) . . . . ? C11 C12 C13 C14 -0.28(19) . . . . ? C12 C13 C14 C15 0.46(18) . . . . ? C12 C13 C14 C17 179.98(11) . . . . ? C13 C14 C15 C16 -0.57(17) . . . . ? C17 C14 C15 C16 179.89(11) . . . . ? C14 C15 C16 C11 0.49(18) . . . . ? N1 C11 C16 C15 -179.2(3) . . . . ? C12 C11 C16 C15 -0.29(19) . . . . ? Cl11 C11 C16 C15 179.27(12) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.69(15) . . . . ? C13 C14 C17 C7 4.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.872 _diffrn_reflns_theta_full 27.80 _diffrn_measured_fraction_theta_full 0.872 _refine_diff_density_max 0.079 _refine_diff_density_min -0.117 _refine_diff_density_rms 0.034 # start Validation Reply Form _vrf_SYMMG02_CNS-DMSOI-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-DMSOI-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.87 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:20. ; # end Validation Reply Form #===END data_CNS-DMSOI-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761234' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.91920(10) _cell_length_b 12.9630(4) _cell_length_c 12.2399(4) _cell_angle_alpha 90.000(2) _cell_angle_beta 93.188(2) _cell_angle_gamma 90.000(2) _cell_volume 620.88(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3483 _cell_measurement_theta_min 3.143 _cell_measurement_theta_max 26.239 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.812887 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3467 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.80 _reflns_number_total 1974 _reflns_number_gt 1393 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.0577P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.022(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(3) _refine_ls_number_reflns 1974 _refine_ls_number_parameters 102 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3706(6) -0.46093(9) -0.1755(2) 0.1125(7) Uani 0.4634(18) 1 d P . . N11 N 0.3629(14) -0.4151(3) -0.1725(4) 0.0828(10) Uani 0.5366(18) 1 d P . . O11 O 0.3160(11) -0.4977(3) -0.1233(3) 0.1301(13) Uani 0.5366(18) 1 d P . . O12 O 0.4983(6) -0.41286(18) -0.25803(18) 0.1132(8) Uani 0.5366(18) 1 d P . . C1 C 0.2615(3) -0.32958(11) -0.12304(10) 0.0746(4) Uani 1 1 d . . . C2 C 0.3147(3) -0.23918(13) -0.17920(9) 0.0805(4) Uani 1 1 d . . . H2A H 0.4118 -0.2406 -0.2468 0.097 Uiso 1 1 calc R . . C3 C 0.2228(3) -0.14754(11) -0.13425(10) 0.0765(4) Uani 1 1 d . . . H3A H 0.2575 -0.0866 -0.1721 0.092 Uiso 1 1 calc R . . C4 C 0.0781(3) -0.14333(9) -0.03285(9) 0.0659(3) Uani 1 1 d . . . C5 C 0.0283(3) -0.23616(10) 0.02061(9) 0.0728(4) Uani 1 1 d . . . H5A H -0.0698 -0.2352 0.0881 0.087 Uiso 1 1 calc R . . C6 C 0.1188(3) -0.32918(10) -0.02261(10) 0.0768(4) Uani 1 1 d . . . H6A H 0.0847 -0.3904 0.0149 0.092 Uiso 1 1 calc R . . C7 C -0.0243(3) -0.04663(9) 0.01842(10) 0.0721(4) Uani 1 1 d . . . H7A H -0.1345 -0.0522 0.0835 0.087 Uiso 1 1 calc R . . Cl11 Cl -0.3706(6) 0.46093(9) 0.1755(2) 0.1125(7) Uani 0.5366(18) 1 d P . . N1 N -0.3629(14) 0.4151(3) 0.1725(4) 0.0828(10) Uani 0.4634(18) 1 d P . . O1 O -0.3160(11) 0.4977(3) 0.1233(3) 0.1301(13) Uani 0.4634(18) 1 d P . . O2 O -0.4983(6) 0.41286(18) 0.25803(18) 0.1132(8) Uani 0.4634(18) 1 d P . . C11 C -0.2615(3) 0.32958(11) 0.12304(10) 0.0746(4) Uani 1 1 d . . . C12 C -0.3147(3) 0.23918(13) 0.17920(9) 0.0805(4) Uani 1 1 d . . . H12A H -0.4118 0.2406 0.2468 0.097 Uiso 1 1 calc R . . C13 C -0.2228(3) 0.14754(11) 0.13425(10) 0.0765(4) Uani 1 1 d . . . H13A H -0.2575 0.0866 0.1721 0.092 Uiso 1 1 calc R . . C14 C -0.0781(3) 0.14333(9) 0.03285(9) 0.0659(3) Uani 1 1 d . . . C15 C -0.0283(3) 0.23616(10) -0.02061(9) 0.0728(4) Uani 1 1 d . . . H15A H 0.0698 0.2352 -0.0881 0.087 Uiso 1 1 calc R . . C16 C -0.1188(3) 0.32918(10) 0.02261(10) 0.0768(4) Uani 1 1 d . . . H16A H -0.0847 0.3904 -0.0149 0.092 Uiso 1 1 calc R . . C17 C 0.0243(3) 0.04663(9) -0.01842(10) 0.0721(4) Uani 1 1 d . . . H17A H 0.1345 0.0522 -0.0835 0.087 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1121(9) 0.0921(15) 0.1331(14) -0.0446(14) 0.0042(8) 0.0235(12) N11 0.0803(18) 0.067(3) 0.100(3) -0.003(2) -0.0036(17) 0.007(2) O11 0.169(3) 0.078(2) 0.147(3) 0.0116(17) 0.040(2) 0.0132(17) O12 0.150(2) 0.0935(17) 0.0985(14) -0.0254(13) 0.0335(14) 0.0191(14) C1 0.0590(7) 0.0880(10) 0.0764(8) -0.0148(7) -0.0014(5) 0.0059(6) C2 0.0695(7) 0.1068(12) 0.0658(7) -0.0031(7) 0.0092(6) -0.0002(7) C3 0.0700(7) 0.0855(10) 0.0745(7) 0.0078(6) 0.0067(6) -0.0036(6) C4 0.0522(6) 0.0787(8) 0.0665(7) -0.0032(6) 0.0009(5) -0.0011(5) C5 0.0690(7) 0.0837(9) 0.0663(7) 0.0020(6) 0.0085(5) -0.0002(6) C6 0.0733(7) 0.0782(9) 0.0791(8) 0.0023(6) 0.0050(6) 0.0017(6) C7 0.0617(6) 0.0839(9) 0.0711(7) 0.0039(6) 0.0064(5) -0.0030(6) Cl11 0.1121(9) 0.0921(15) 0.1331(14) -0.0446(14) 0.0042(8) 0.0235(12) N1 0.0803(18) 0.067(3) 0.100(3) -0.003(2) -0.0036(17) 0.007(2) O1 0.169(3) 0.078(2) 0.147(3) 0.0116(17) 0.040(2) 0.0132(17) O2 0.150(2) 0.0935(17) 0.0985(14) -0.0254(13) 0.0335(14) 0.0191(14) C11 0.0590(7) 0.0880(10) 0.0764(8) -0.0148(7) -0.0014(5) 0.0059(6) C12 0.0695(7) 0.1068(12) 0.0658(7) -0.0031(7) 0.0092(6) -0.0002(7) C13 0.0700(7) 0.0855(10) 0.0745(7) 0.0078(6) 0.0067(6) -0.0036(6) C14 0.0522(6) 0.0787(8) 0.0665(7) -0.0032(6) 0.0009(5) -0.0011(5) C15 0.0690(7) 0.0837(9) 0.0663(7) 0.0020(6) 0.0085(5) -0.0002(6) C16 0.0733(7) 0.0782(9) 0.0791(8) 0.0023(6) 0.0050(6) 0.0017(6) C17 0.0617(6) 0.0839(9) 0.0711(7) 0.0039(6) 0.0064(5) -0.0030(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.597(4) . ? Cl1 O11 0.835(3) . ? Cl1 O12 1.310(3) . ? Cl1 C1 1.8776(18) . ? N11 O12 1.201(6) . ? N11 O11 1.248(7) . ? N11 C1 1.333(4) . ? C1 C6 1.3787(18) . ? C1 C2 1.3802(19) . ? C2 C3 1.3659(19) . ? C2 H2A 0.9300 . ? C3 C4 1.3940(17) . ? C3 H3A 0.9300 . ? C4 C5 1.3887(17) . ? C4 C7 1.4678(17) . ? C5 C6 1.3713(17) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.308(2) . ? C7 H7A 0.9300 . ? Cl11 N1 0.597(4) . ? Cl11 O1 0.835(3) . ? Cl11 O2 1.310(3) . ? Cl11 C11 1.8776(18) . ? N1 O2 1.201(6) . ? N1 O1 1.248(7) . ? N1 C11 1.333(4) . ? C11 C16 1.3787(18) . ? C11 C12 1.3802(19) . ? C12 C13 1.3659(19) . ? C12 H12A 0.9300 . ? C13 C14 1.3940(17) . ? C13 H13A 0.9300 . ? C14 C15 1.3887(17) . ? C14 C17 1.4678(17) . ? C15 C16 1.3713(17) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 120.3(10) . . ? N11 Cl1 O12 66.2(7) . . ? O11 Cl1 O12 170.9(4) . . ? N11 Cl1 C1 20.2(7) . . ? O11 Cl1 C1 100.6(4) . . ? O12 Cl1 C1 86.35(13) . . ? Cl1 N11 O12 86.7(7) . . ? Cl1 N11 O11 35.3(7) . . ? O12 N11 O11 121.7(4) . . ? Cl1 N11 C1 150.9(10) . . ? O12 N11 C1 122.2(4) . . ? O11 N11 C1 116.1(4) . . ? Cl1 O11 N11 24.4(3) . . ? N11 O12 Cl1 27.06(17) . . ? N11 C1 C6 123.6(3) . . ? N11 C1 C2 115.0(3) . . ? C6 C1 C2 121.39(13) . . ? N11 C1 Cl1 8.9(3) . . ? C6 C1 Cl1 114.83(14) . . ? C2 C1 Cl1 123.78(13) . . ? C3 C2 C1 119.16(12) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.47(13) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.42(12) . . ? C5 C4 C7 119.32(11) . . ? C3 C4 C7 123.27(12) . . ? C6 C5 C4 122.29(11) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C5 C6 C1 118.27(13) . . ? C5 C6 H6A 120.9 . . ? C1 C6 H6A 120.9 . . ? C17 C7 C4 126.40(15) . . ? C17 C7 H7A 116.8 . . ? C4 C7 H7A 116.8 . . ? N1 Cl11 O1 120.3(10) . . ? N1 Cl11 O2 66.2(7) . . ? O1 Cl11 O2 170.9(4) . . ? N1 Cl11 C11 20.2(7) . . ? O1 Cl11 C11 100.6(4) . . ? O2 Cl11 C11 86.35(13) . . ? Cl11 N1 O2 86.7(7) . . ? Cl11 N1 O1 35.3(7) . . ? O2 N1 O1 121.7(4) . . ? Cl11 N1 C11 150.9(10) . . ? O2 N1 C11 122.2(4) . . ? O1 N1 C11 116.1(4) . . ? Cl11 O1 N1 24.4(3) . . ? N1 O2 Cl11 27.06(17) . . ? N1 C11 C16 123.6(3) . . ? N1 C11 C12 115.0(3) . . ? C16 C11 C12 121.39(13) . . ? N1 C11 Cl11 8.9(3) . . ? C16 C11 Cl11 114.83(14) . . ? C12 C11 Cl11 123.78(13) . . ? C13 C12 C11 119.16(12) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 121.47(13) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 117.42(12) . . ? C15 C14 C17 119.32(11) . . ? C13 C14 C17 123.27(12) . . ? C16 C15 C14 122.29(11) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C15 C16 C11 118.27(13) . . ? C15 C16 H16A 120.9 . . ? C11 C16 H16A 120.9 . . ? C7 C17 C14 126.40(15) . . ? C7 C17 H17A 116.8 . . ? C14 C17 H17A 116.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.9(5) . . . . ? C1 Cl1 N11 O12 -175(2) . . . . ? O12 Cl1 N11 O11 -172.9(5) . . . . ? C1 Cl1 N11 O11 12(2) . . . . ? O11 Cl1 N11 C1 -12(2) . . . . ? O12 Cl1 N11 C1 175(2) . . . . ? O12 Cl1 O11 N11 135(3) . . . . ? C1 Cl1 O11 N11 -4.3(8) . . . . ? O12 N11 O11 Cl1 -8.3(6) . . . . ? C1 N11 O11 Cl1 173.3(12) . . . . ? O11 N11 O12 Cl1 4.8(4) . . . . ? C1 N11 O12 Cl1 -176.9(11) . . . . ? O11 Cl1 O12 N11 -138(3) . . . . ? C1 Cl1 O12 N11 1.9(7) . . . . ? Cl1 N11 C1 C6 9(2) . . . . ? O12 N11 C1 C6 -177.1(3) . . . . ? O11 N11 C1 C6 1.3(6) . . . . ? Cl1 N11 C1 C2 -171.8(18) . . . . ? O12 N11 C1 C2 1.9(6) . . . . ? O11 N11 C1 C2 -179.7(4) . . . . ? O12 N11 C1 Cl1 174(2) . . . . ? O11 N11 C1 Cl1 -8.0(15) . . . . ? O11 Cl1 C1 N11 169(2) . . . . ? O12 Cl1 C1 N11 -4.9(18) . . . . ? N11 Cl1 C1 C6 -171.5(19) . . . . ? O11 Cl1 C1 C6 -2.4(4) . . . . ? O12 Cl1 C1 C6 -176.46(15) . . . . ? N11 Cl1 C1 C2 9.0(19) . . . . ? O11 Cl1 C1 C2 178.1(3) . . . . ? O12 Cl1 C1 C2 4.1(2) . . . . ? N11 C1 C2 C3 -179.2(3) . . . . ? C6 C1 C2 C3 -0.17(18) . . . . ? Cl1 C1 C2 C3 179.29(12) . . . . ? C1 C2 C3 C4 0.27(18) . . . . ? C2 C3 C4 C5 -0.47(17) . . . . ? C2 C3 C4 C7 -179.99(10) . . . . ? C3 C4 C5 C6 0.59(17) . . . . ? C7 C4 C5 C6 -179.87(10) . . . . ? C4 C5 C6 C1 -0.49(17) . . . . ? N11 C1 C6 C5 179.2(3) . . . . ? C2 C1 C6 C5 0.27(18) . . . . ? Cl1 C1 C6 C5 -179.23(12) . . . . ? C5 C4 C7 C17 175.69(14) . . . . ? C3 C4 C7 C17 -4.8(2) . . . . ? O1 Cl11 N1 O2 -172.9(5) . . . . ? C11 Cl11 N1 O2 175(2) . . . . ? O2 Cl11 N1 O1 172.9(5) . . . . ? C11 Cl11 N1 O1 -12(2) . . . . ? O1 Cl11 N1 C11 12(2) . . . . ? O2 Cl11 N1 C11 -175(2) . . . . ? O2 Cl11 O1 N1 -135(3) . . . . ? C11 Cl11 O1 N1 4.3(8) . . . . ? O2 N1 O1 Cl11 8.3(6) . . . . ? C11 N1 O1 Cl11 -173.3(12) . . . . ? O1 N1 O2 Cl11 -4.8(4) . . . . ? C11 N1 O2 Cl11 176.9(11) . . . . ? O1 Cl11 O2 N1 138(3) . . . . ? C11 Cl11 O2 N1 -1.9(7) . . . . ? Cl11 N1 C11 C16 -9(2) . . . . ? O2 N1 C11 C16 177.1(3) . . . . ? O1 N1 C11 C16 -1.3(6) . . . . ? Cl11 N1 C11 C12 171.8(18) . . . . ? O2 N1 C11 C12 -1.9(6) . . . . ? O1 N1 C11 C12 179.7(4) . . . . ? O2 N1 C11 Cl11 -174(2) . . . . ? O1 N1 C11 Cl11 8.0(15) . . . . ? O1 Cl11 C11 N1 -169(2) . . . . ? O2 Cl11 C11 N1 4.9(18) . . . . ? N1 Cl11 C11 C16 171.5(19) . . . . ? O1 Cl11 C11 C16 2.4(4) . . . . ? O2 Cl11 C11 C16 176.46(15) . . . . ? N1 Cl11 C11 C12 -9.0(19) . . . . ? O1 Cl11 C11 C12 -178.1(3) . . . . ? O2 Cl11 C11 C12 -4.1(2) . . . . ? N1 C11 C12 C13 179.2(3) . . . . ? C16 C11 C12 C13 0.17(18) . . . . ? Cl11 C11 C12 C13 -179.29(12) . . . . ? C11 C12 C13 C14 -0.27(18) . . . . ? C12 C13 C14 C15 0.47(17) . . . . ? C12 C13 C14 C17 179.99(10) . . . . ? C13 C14 C15 C16 -0.59(17) . . . . ? C17 C14 C15 C16 179.87(10) . . . . ? C14 C15 C16 C11 0.49(17) . . . . ? N1 C11 C16 C15 -179.2(3) . . . . ? C12 C11 C16 C15 -0.27(18) . . . . ? Cl11 C11 C16 C15 179.23(12) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.69(14) . . . . ? C13 C14 C17 C7 4.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 27.80 _diffrn_measured_fraction_theta_full 0.911 _refine_diff_density_max 0.084 _refine_diff_density_min -0.124 _refine_diff_density_rms 0.035 # start Validation Reply Form _vrf_SYMMG02_CNS-DMSOI-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-DMSOI-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.91 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:20. ; # end Validation Reply Form #===END data_CNS-DMSOII-small-P21/c _database_code_depnum_ccdc_archive 'CCDC 761235' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall 'P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.91730(10) _cell_length_b 12.9563(3) _cell_length_c 12.2343(3) _cell_angle_alpha 90.0000(10) _cell_angle_beta 93.1510(10) _cell_angle_gamma 90.0000(10) _cell_volume 620.00(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6660 _cell_measurement_theta_min 3.1445 _cell_measurement_theta_max 26.2435 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.901005 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6625 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.81 _reflns_number_total 2669 _reflns_number_gt 1932 _reflns_threshold_expression I>2sigma(I) _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+0.0667P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.018(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2669 _refine_ls_number_parameters 102 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3707(5) -0.46097(7) -0.17557(18) 0.1131(6) Uani 0.50 1 d P . . N11 N 0.3619(11) -0.4155(2) -0.1724(4) 0.0815(9) Uani 0.50 1 d P . . O11 O 0.3165(10) -0.4975(3) -0.1231(3) 0.1302(12) Uani 0.50 1 d P . . O12 O 0.4981(6) -0.41270(16) -0.25815(17) 0.1142(7) Uani 0.50 1 d P . . C1 C 0.2613(3) -0.32956(9) -0.12301(10) 0.0746(3) Uani 1 1 d . . . C2 C 0.3149(3) -0.23915(11) -0.17924(9) 0.0803(3) Uani 1 1 d . . . H2A H 0.4124 -0.2407 -0.2469 0.096 Uiso 1 1 calc R . . C3 C 0.2230(3) -0.14738(9) -0.13426(9) 0.0762(3) Uani 1 1 d . . . H3A H 0.2579 -0.0864 -0.1721 0.091 Uiso 1 1 calc R . . C4 C 0.0780(2) -0.14336(8) -0.03286(8) 0.0657(3) Uani 1 1 d . . . C5 C 0.0281(3) -0.23613(9) 0.02066(9) 0.0725(3) Uani 1 1 d . . . H5A H -0.0701 -0.2352 0.0882 0.087 Uiso 1 1 calc R . . C6 C 0.1188(3) -0.32928(9) -0.02270(10) 0.0767(3) Uani 1 1 d . . . H6A H 0.0848 -0.3906 0.0147 0.092 Uiso 1 1 calc R . . C7 C -0.0243(3) -0.04660(8) 0.01841(9) 0.0718(3) Uani 1 1 d . . . H7A H -0.1346 -0.0522 0.0835 0.086 Uiso 1 1 calc R . . Cl11 Cl -0.3707(5) 0.46097(7) 0.17557(18) 0.1131(6) Uani 0.50 1 d P . . N1 N -0.3619(11) 0.4155(2) 0.1724(4) 0.0815(9) Uani 0.50 1 d P . . O1 O -0.3165(10) 0.4975(3) 0.1231(3) 0.1302(12) Uani 0.50 1 d P . . O2 O -0.4981(6) 0.41270(16) 0.25815(17) 0.1142(7) Uani 0.50 1 d P . . C11 C -0.2613(3) 0.32956(9) 0.12301(10) 0.0746(3) Uani 1 1 d . . . C12 C -0.3149(3) 0.23915(11) 0.17924(9) 0.0803(3) Uani 1 1 d . . . H12A H -0.4124 0.2407 0.2469 0.096 Uiso 1 1 calc R . . C13 C -0.2230(3) 0.14738(9) 0.13426(9) 0.0762(3) Uani 1 1 d . . . H13A H -0.2579 0.0864 0.1721 0.091 Uiso 1 1 calc R . . C14 C -0.0780(2) 0.14336(8) 0.03286(8) 0.0657(3) Uani 1 1 d . . . C15 C -0.0281(3) 0.23613(9) -0.02066(9) 0.0725(3) Uani 1 1 d . . . H15A H 0.0701 0.2352 -0.0882 0.087 Uiso 1 1 calc R . . C16 C -0.1188(3) 0.32928(9) 0.02270(10) 0.0767(3) Uani 1 1 d . . . H16A H -0.0848 0.3906 -0.0147 0.092 Uiso 1 1 calc R . . C17 C 0.0243(3) 0.04660(8) -0.01841(9) 0.0718(3) Uani 1 1 d . . . H17A H 0.1346 0.0522 -0.0835 0.086 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1125(8) 0.0934(13) 0.1330(12) -0.0455(12) 0.0036(8) 0.0250(10) N11 0.0786(16) 0.068(2) 0.097(2) -0.0039(19) -0.0012(14) 0.0081(18) O11 0.170(2) 0.0778(16) 0.146(3) 0.0103(15) 0.0401(19) 0.0141(15) O12 0.1510(19) 0.0945(14) 0.0999(14) -0.0264(12) 0.0315(13) 0.0204(12) C1 0.0585(6) 0.0886(8) 0.0760(7) -0.0145(6) -0.0012(5) 0.0056(5) C2 0.0688(7) 0.1079(9) 0.0648(7) -0.0033(6) 0.0092(5) -0.0009(6) C3 0.0697(7) 0.0859(8) 0.0734(7) 0.0074(6) 0.0076(5) -0.0039(5) C4 0.0517(5) 0.0790(7) 0.0663(6) -0.0023(5) 0.0012(4) -0.0017(4) C5 0.0677(6) 0.0849(8) 0.0654(6) 0.0018(5) 0.0087(5) -0.0001(5) C6 0.0732(7) 0.0789(7) 0.0781(7) 0.0026(6) 0.0044(5) 0.0020(5) C7 0.0610(6) 0.0835(7) 0.0711(6) 0.0032(5) 0.0069(5) -0.0027(5) Cl11 0.1125(8) 0.0934(13) 0.1330(12) -0.0455(12) 0.0036(8) 0.0250(10) N1 0.0786(16) 0.068(2) 0.097(2) -0.0039(19) -0.0012(14) 0.0081(18) O1 0.170(2) 0.0778(16) 0.146(3) 0.0103(15) 0.0401(19) 0.0141(15) O2 0.1510(19) 0.0945(14) 0.0999(14) -0.0264(12) 0.0315(13) 0.0204(12) C11 0.0585(6) 0.0886(8) 0.0760(7) -0.0145(6) -0.0012(5) 0.0056(5) C12 0.0688(7) 0.1079(9) 0.0648(7) -0.0033(6) 0.0092(5) -0.0009(6) C13 0.0697(7) 0.0859(8) 0.0734(7) 0.0074(6) 0.0076(5) -0.0039(5) C14 0.0517(5) 0.0790(7) 0.0663(6) -0.0023(5) 0.0012(4) -0.0017(4) C15 0.0677(6) 0.0849(8) 0.0654(6) 0.0018(5) 0.0087(5) -0.0001(5) C16 0.0732(7) 0.0789(7) 0.0781(7) 0.0026(6) 0.0044(5) 0.0020(5) C17 0.0610(6) 0.0835(7) 0.0711(6) 0.0032(5) 0.0069(5) -0.0027(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.592(3) . ? Cl1 O11 0.835(3) . ? Cl1 O12 1.310(3) . ? Cl1 C1 1.8777(15) . ? N11 O12 1.204(5) . ? N11 O11 1.240(6) . ? N11 C1 1.336(3) . ? C1 C6 1.3759(16) . ? C1 C2 1.3804(17) . ? C2 C3 1.3668(17) . ? C2 H2A 0.9300 . ? C3 C4 1.3934(15) . ? C3 H3A 0.9300 . ? C4 C5 1.3878(15) . ? C4 C7 1.4674(15) . ? C5 C6 1.3730(15) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.306(2) . ? C7 H7A 0.9300 . ? Cl11 N1 0.592(3) . ? Cl11 O1 0.835(3) . ? Cl11 O2 1.310(3) . ? Cl11 C11 1.8777(15) . ? N1 O2 1.204(5) . ? N1 O1 1.240(6) . ? N1 C11 1.336(3) . ? C11 C16 1.3759(16) . ? C11 C12 1.3804(17) . ? C12 C13 1.3668(17) . ? C12 H12A 0.9300 . ? C13 C14 1.3934(15) . ? C13 H13A 0.9300 . ? C14 C15 1.3878(15) . ? C14 C17 1.4674(15) . ? C15 C16 1.3730(15) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 119.8(8) . . ? N11 Cl1 O12 66.5(6) . . ? O11 Cl1 O12 171.1(4) . . ? N11 Cl1 C1 19.8(6) . . ? O11 Cl1 C1 100.3(3) . . ? O12 Cl1 C1 86.28(11) . . ? Cl1 N11 O12 86.7(6) . . ? Cl1 N11 O11 35.8(6) . . ? O12 N11 O11 122.1(3) . . ? Cl1 N11 C1 151.5(8) . . ? O12 N11 C1 121.7(3) . . ? O11 N11 C1 116.1(3) . . ? Cl1 O11 N11 24.5(3) . . ? N11 O12 Cl1 26.80(14) . . ? N11 C1 C6 123.3(2) . . ? N11 C1 C2 115.1(2) . . ? C6 C1 C2 121.51(11) . . ? N11 C1 Cl1 8.6(3) . . ? C6 C1 Cl1 114.79(12) . . ? C2 C1 Cl1 123.70(11) . . ? C3 C2 C1 119.14(11) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.35(11) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.56(10) . . ? C5 C4 C7 119.30(10) . . ? C3 C4 C7 123.14(10) . . ? C6 C5 C4 122.19(10) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C5 C6 C1 118.25(11) . . ? C5 C6 H6A 120.9 . . ? C1 C6 H6A 120.9 . . ? C17 C7 C4 126.44(14) . . ? C17 C7 H7A 116.8 . . ? C4 C7 H7A 116.8 . . ? N1 Cl11 O1 119.8(8) . . ? N1 Cl11 O2 66.5(6) . . ? O1 Cl11 O2 171.1(4) . . ? N1 Cl11 C11 19.8(6) . . ? O1 Cl11 C11 100.3(3) . . ? O2 Cl11 C11 86.28(11) . . ? Cl11 N1 O2 86.7(6) . . ? Cl11 N1 O1 35.8(6) . . ? O2 N1 O1 122.1(3) . . ? Cl11 N1 C11 151.5(8) . . ? O2 N1 C11 121.7(3) . . ? O1 N1 C11 116.1(3) . . ? Cl11 O1 N1 24.5(3) . . ? N1 O2 Cl11 26.80(14) . . ? N1 C11 C16 123.3(2) . . ? N1 C11 C12 115.1(2) . . ? C16 C11 C12 121.51(11) . . ? N1 C11 Cl11 8.6(3) . . ? C16 C11 Cl11 114.79(12) . . ? C12 C11 Cl11 123.70(11) . . ? C13 C12 C11 119.14(11) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 121.35(11) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 117.56(10) . . ? C15 C14 C17 119.30(10) . . ? C13 C14 C17 123.14(10) . . ? C16 C15 C14 122.19(10) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C15 C16 C11 118.25(11) . . ? C15 C16 H16A 120.9 . . ? C11 C16 H16A 120.9 . . ? C7 C17 C14 126.44(14) . . ? C7 C17 H17A 116.8 . . ? C14 C17 H17A 116.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.9(5) . . . . ? C1 Cl1 N11 O12 -175.3(16) . . . . ? O12 Cl1 N11 O11 -172.9(5) . . . . ? C1 Cl1 N11 O11 11.8(19) . . . . ? O11 Cl1 N11 C1 -11.8(19) . . . . ? O12 Cl1 N11 C1 175.3(16) . . . . ? O12 Cl1 O11 N11 133(3) . . . . ? C1 Cl1 O11 N11 -4.0(6) . . . . ? O12 N11 O11 Cl1 -8.4(6) . . . . ? C1 N11 O11 Cl1 173.8(10) . . . . ? O11 N11 O12 Cl1 4.9(3) . . . . ? C1 N11 O12 Cl1 -177.4(9) . . . . ? O11 Cl1 O12 N11 -136(3) . . . . ? C1 Cl1 O12 N11 1.6(5) . . . . ? Cl1 N11 C1 C6 8.5(17) . . . . ? O12 N11 C1 C6 -177.0(3) . . . . ? O11 N11 C1 C6 0.8(5) . . . . ? Cl1 N11 C1 C2 -172.5(15) . . . . ? O12 N11 C1 C2 2.1(5) . . . . ? O11 N11 C1 C2 179.9(3) . . . . ? O12 N11 C1 Cl1 174.5(19) . . . . ? O11 N11 C1 Cl1 -7.6(12) . . . . ? O11 Cl1 C1 N11 169.6(17) . . . . ? O12 Cl1 C1 N11 -4.3(15) . . . . ? N11 Cl1 C1 C6 -172.2(15) . . . . ? O11 Cl1 C1 C6 -2.6(4) . . . . ? O12 Cl1 C1 C6 -176.49(14) . . . . ? N11 Cl1 C1 C2 8.2(16) . . . . ? O11 Cl1 C1 C2 177.8(3) . . . . ? O12 Cl1 C1 C2 3.90(18) . . . . ? N11 C1 C2 C3 -179.3(2) . . . . ? C6 C1 C2 C3 -0.25(17) . . . . ? Cl1 C1 C2 C3 179.33(11) . . . . ? C1 C2 C3 C4 0.28(17) . . . . ? C2 C3 C4 C5 -0.41(16) . . . . ? C2 C3 C4 C7 179.99(10) . . . . ? C3 C4 C5 C6 0.53(16) . . . . ? C7 C4 C5 C6 -179.85(10) . . . . ? C4 C5 C6 C1 -0.51(17) . . . . ? N11 C1 C6 C5 179.3(2) . . . . ? C2 C1 C6 C5 0.36(17) . . . . ? Cl1 C1 C6 C5 -179.26(10) . . . . ? C5 C4 C7 C17 175.68(13) . . . . ? C3 C4 C7 C17 -4.7(2) . . . . ? O1 Cl11 N1 O2 -172.9(5) . . . . ? C11 Cl11 N1 O2 175.3(16) . . . . ? O2 Cl11 N1 O1 172.9(5) . . . . ? C11 Cl11 N1 O1 -11.8(19) . . . . ? O1 Cl11 N1 C11 11.8(19) . . . . ? O2 Cl11 N1 C11 -175.3(16) . . . . ? O2 Cl11 O1 N1 -133(3) . . . . ? C11 Cl11 O1 N1 4.0(6) . . . . ? O2 N1 O1 Cl11 8.4(6) . . . . ? C11 N1 O1 Cl11 -173.8(10) . . . . ? O1 N1 O2 Cl11 -4.9(3) . . . . ? C11 N1 O2 Cl11 177.4(9) . . . . ? O1 Cl11 O2 N1 136(3) . . . . ? C11 Cl11 O2 N1 -1.6(5) . . . . ? Cl11 N1 C11 C16 -8.5(17) . . . . ? O2 N1 C11 C16 177.0(3) . . . . ? O1 N1 C11 C16 -0.8(5) . . . . ? Cl11 N1 C11 C12 172.5(15) . . . . ? O2 N1 C11 C12 -2.1(5) . . . . ? O1 N1 C11 C12 -179.9(3) . . . . ? O2 N1 C11 Cl11 -174.5(19) . . . . ? O1 N1 C11 Cl11 7.6(12) . . . . ? O1 Cl11 C11 N1 -169.6(17) . . . . ? O2 Cl11 C11 N1 4.3(15) . . . . ? N1 Cl11 C11 C16 172.2(15) . . . . ? O1 Cl11 C11 C16 2.6(4) . . . . ? O2 Cl11 C11 C16 176.49(14) . . . . ? N1 Cl11 C11 C12 -8.2(16) . . . . ? O1 Cl11 C11 C12 -177.8(3) . . . . ? O2 Cl11 C11 C12 -3.90(18) . . . . ? N1 C11 C12 C13 179.3(2) . . . . ? C16 C11 C12 C13 0.25(17) . . . . ? Cl11 C11 C12 C13 -179.33(11) . . . . ? C11 C12 C13 C14 -0.28(17) . . . . ? C12 C13 C14 C15 0.41(16) . . . . ? C12 C13 C14 C17 -179.99(10) . . . . ? C13 C14 C15 C16 -0.53(16) . . . . ? C17 C14 C15 C16 179.85(10) . . . . ? C14 C15 C16 C11 0.51(17) . . . . ? N1 C11 C16 C15 -179.3(2) . . . . ? C12 C11 C16 C15 -0.36(17) . . . . ? Cl11 C11 C16 C15 179.26(10) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.68(13) . . . . ? C13 C14 C17 C7 4.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 27.81 _diffrn_measured_fraction_theta_full 0.898 _refine_diff_density_max 0.095 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.036 # start Validation Reply Form _vrf_SYMMG02_CNS-DMSOII-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-DMSOII-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.90 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:27. ; # end Validation Reply Form #===END data_CNS-DMSOII-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761236' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall 'P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.91730(10) _cell_length_b 12.9563(3) _cell_length_c 12.2343(3) _cell_angle_alpha 90.0000(10) _cell_angle_beta 93.1510(10) _cell_angle_gamma 90.0000(10) _cell_volume 620.00(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6660 _cell_measurement_theta_min 3.1445 _cell_measurement_theta_max 26.2435 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.901005 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6625 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.81 _reflns_number_total 2669 _reflns_number_gt 1932 _reflns_threshold_expression I>2sigma(I) _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+0.0667P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(2) _refine_ls_number_reflns 2669 _refine_ls_number_parameters 102 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1082 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3708(5) -0.46091(7) -0.17576(17) 0.1134(6) Uani 0.4604(16) 1 d P . . N11 N 0.3620(10) -0.4156(2) -0.1721(3) 0.0819(8) Uani 0.5396(16) 1 d P . . O11 O 0.3163(9) -0.4973(2) -0.1232(2) 0.1298(11) Uani 0.5396(16) 1 d P . . O12 O 0.4983(6) -0.41279(15) -0.25813(16) 0.1135(7) Uani 0.5396(16) 1 d P . . C1 C 0.2614(3) -0.32956(9) -0.12304(9) 0.0745(3) Uani 1 1 d . . . C2 C 0.3149(3) -0.23910(10) -0.17931(9) 0.0802(3) Uani 1 1 d . . . H2A H 0.4123 -0.2406 -0.2469 0.096 Uiso 1 1 calc R . . C3 C 0.2229(3) -0.14740(9) -0.13428(9) 0.0763(3) Uani 1 1 d . . . H3A H 0.2578 -0.0864 -0.1721 0.092 Uiso 1 1 calc R . . C4 C 0.0780(2) -0.14334(8) -0.03289(8) 0.0657(3) Uani 1 1 d . . . C5 C 0.0281(2) -0.23613(8) 0.02066(8) 0.0725(3) Uani 1 1 d . . . H5A H -0.0702 -0.2352 0.0881 0.087 Uiso 1 1 calc R . . C6 C 0.1188(3) -0.32924(8) -0.02265(9) 0.0765(3) Uani 1 1 d . . . H6A H 0.0849 -0.3905 0.0148 0.092 Uiso 1 1 calc R . . C7 C -0.0242(2) -0.04664(7) 0.01841(9) 0.0715(3) Uani 1 1 d . . . H7A H -0.1344 -0.0522 0.0836 0.086 Uiso 1 1 calc R . . Cl11 Cl -0.3708(5) 0.46091(7) 0.17576(17) 0.1134(6) Uani 0.5396(16) 1 d P . . N1 N -0.3620(10) 0.4156(2) 0.1721(3) 0.0819(8) Uani 0.4604(16) 1 d P . . O1 O -0.3163(9) 0.4973(2) 0.1232(2) 0.1298(11) Uani 0.4604(16) 1 d P . . O2 O -0.4983(6) 0.41279(15) 0.25813(16) 0.1135(7) Uani 0.4604(16) 1 d P . . C11 C -0.2614(3) 0.32956(9) 0.12304(9) 0.0745(3) Uani 1 1 d . . . C12 C -0.3149(3) 0.23910(10) 0.17931(9) 0.0802(3) Uani 1 1 d . . . H12A H -0.4123 0.2406 0.2469 0.096 Uiso 1 1 calc R . . C13 C -0.2229(3) 0.14740(9) 0.13428(9) 0.0763(3) Uani 1 1 d . . . H13A H -0.2578 0.0864 0.1721 0.092 Uiso 1 1 calc R . . C14 C -0.0780(2) 0.14334(8) 0.03289(8) 0.0657(3) Uani 1 1 d . . . C15 C -0.0281(2) 0.23613(8) -0.02066(8) 0.0725(3) Uani 1 1 d . . . H15A H 0.0702 0.2352 -0.0881 0.087 Uiso 1 1 calc R . . C16 C -0.1188(3) 0.32924(8) 0.02265(9) 0.0765(3) Uani 1 1 d . . . H16A H -0.0849 0.3905 -0.0148 0.092 Uiso 1 1 calc R . . C17 C 0.0242(2) 0.04664(7) -0.01841(9) 0.0715(3) Uani 1 1 d . . . H17A H 0.1344 0.0522 -0.0836 0.086 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1122(7) 0.0943(12) 0.1333(11) -0.0464(12) 0.0035(7) 0.0250(9) N11 0.0786(15) 0.069(2) 0.097(2) -0.0051(18) -0.0019(14) 0.0080(17) O11 0.168(2) 0.0788(15) 0.146(2) 0.0100(14) 0.0400(18) 0.0141(14) O12 0.1513(18) 0.0941(13) 0.0981(13) -0.0250(11) 0.0330(12) 0.0199(12) C1 0.0583(6) 0.0889(8) 0.0759(7) -0.0144(6) -0.0011(5) 0.0056(5) C2 0.0686(6) 0.1077(9) 0.0648(6) -0.0034(6) 0.0094(5) -0.0006(6) C3 0.0694(6) 0.0861(7) 0.0737(7) 0.0077(5) 0.0072(5) -0.0040(5) C4 0.0516(5) 0.0792(6) 0.0660(6) -0.0023(5) 0.0011(4) -0.0017(4) C5 0.0675(6) 0.0852(7) 0.0654(6) 0.0020(5) 0.0089(5) 0.0000(5) C6 0.0732(6) 0.0786(7) 0.0778(7) 0.0025(5) 0.0047(5) 0.0018(5) C7 0.0609(6) 0.0833(7) 0.0708(6) 0.0031(5) 0.0068(5) -0.0027(5) Cl11 0.1122(7) 0.0943(12) 0.1333(11) -0.0464(12) 0.0035(7) 0.0250(9) N1 0.0786(15) 0.069(2) 0.097(2) -0.0051(18) -0.0019(14) 0.0080(17) O1 0.168(2) 0.0788(15) 0.146(2) 0.0100(14) 0.0400(18) 0.0141(14) O2 0.1513(18) 0.0941(13) 0.0981(13) -0.0250(11) 0.0330(12) 0.0199(12) C11 0.0583(6) 0.0889(8) 0.0759(7) -0.0144(6) -0.0011(5) 0.0056(5) C12 0.0686(6) 0.1077(9) 0.0648(6) -0.0034(6) 0.0094(5) -0.0006(6) C13 0.0694(6) 0.0861(7) 0.0737(7) 0.0077(5) 0.0072(5) -0.0040(5) C14 0.0516(5) 0.0792(6) 0.0660(6) -0.0023(5) 0.0011(4) -0.0017(4) C15 0.0675(6) 0.0852(7) 0.0654(6) 0.0020(5) 0.0089(5) 0.0000(5) C16 0.0732(6) 0.0786(7) 0.0778(7) 0.0025(5) 0.0047(5) 0.0018(5) C17 0.0609(6) 0.0833(7) 0.0708(6) 0.0031(5) 0.0068(5) -0.0027(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.590(3) . ? Cl1 O11 0.835(3) . ? Cl1 O12 1.307(3) . ? Cl1 C1 1.8779(14) . ? N11 O12 1.206(5) . ? N11 O11 1.234(5) . ? N11 C1 1.335(3) . ? C1 C6 1.3768(15) . ? C1 C2 1.3811(16) . ? C2 C3 1.3662(16) . ? C2 H2A 0.9300 . ? C3 C4 1.3932(15) . ? C3 H3A 0.9300 . ? C4 C5 1.3881(14) . ? C4 C7 1.4669(14) . ? C5 C6 1.3723(14) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.3072(19) . ? C7 H7A 0.9300 . ? Cl11 N1 0.590(3) . ? Cl11 O1 0.835(3) . ? Cl11 O2 1.307(3) . ? Cl11 C11 1.8779(14) . ? N1 O2 1.206(5) . ? N1 O1 1.234(5) . ? N1 C11 1.335(3) . ? C11 C16 1.3768(15) . ? C11 C12 1.3811(16) . ? C12 C13 1.3662(16) . ? C12 H12A 0.9300 . ? C13 C14 1.3932(15) . ? C13 H13A 0.9300 . ? C14 C15 1.3881(14) . ? C14 C17 1.4669(14) . ? C15 C16 1.3723(14) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 119.0(8) . . ? N11 Cl1 O12 67.0(6) . . ? O11 Cl1 O12 171.2(3) . . ? N11 Cl1 C1 19.4(5) . . ? O11 Cl1 C1 100.0(3) . . ? O12 Cl1 C1 86.36(11) . . ? Cl1 N11 O12 86.2(5) . . ? Cl1 N11 O11 36.3(5) . . ? O12 N11 O11 122.1(3) . . ? Cl1 N11 C1 152.2(8) . . ? O12 N11 C1 121.5(3) . . ? O11 N11 C1 116.3(3) . . ? Cl1 O11 N11 24.7(3) . . ? N11 O12 Cl1 26.79(14) . . ? N11 C1 C6 123.2(2) . . ? N11 C1 C2 115.3(2) . . ? C6 C1 C2 121.48(10) . . ? N11 C1 Cl1 8.4(2) . . ? C6 C1 Cl1 114.87(11) . . ? C2 C1 Cl1 123.65(11) . . ? C3 C2 C1 119.09(10) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 121.42(11) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.54(10) . . ? C5 C4 C7 119.27(9) . . ? C3 C4 C7 123.19(10) . . ? C6 C5 C4 122.20(10) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C5 C6 C1 118.26(10) . . ? C5 C6 H6A 120.9 . . ? C1 C6 H6A 120.9 . . ? C17 C7 C4 126.44(13) . . ? C17 C7 H7A 116.8 . . ? C4 C7 H7A 116.8 . . ? N1 Cl11 O1 119.0(8) . . ? N1 Cl11 O2 67.0(6) . . ? O1 Cl11 O2 171.2(3) . . ? N1 Cl11 C11 19.4(5) . . ? O1 Cl11 C11 100.0(3) . . ? O2 Cl11 C11 86.36(11) . . ? Cl11 N1 O2 86.2(5) . . ? Cl11 N1 O1 36.3(5) . . ? O2 N1 O1 122.1(3) . . ? Cl11 N1 C11 152.2(8) . . ? O2 N1 C11 121.5(3) . . ? O1 N1 C11 116.3(3) . . ? Cl11 O1 N1 24.7(3) . . ? N1 O2 Cl11 26.79(14) . . ? N1 C11 C16 123.2(2) . . ? N1 C11 C12 115.3(2) . . ? C16 C11 C12 121.48(10) . . ? N1 C11 Cl11 8.4(2) . . ? C16 C11 Cl11 114.87(11) . . ? C12 C11 Cl11 123.65(11) . . ? C13 C12 C11 119.09(10) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C14 121.42(11) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 117.54(10) . . ? C15 C14 C17 119.27(9) . . ? C13 C14 C17 123.19(10) . . ? C16 C15 C14 122.20(10) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C15 C16 C11 118.26(10) . . ? C15 C16 H16A 120.9 . . ? C11 C16 H16A 120.9 . . ? C7 C17 C14 126.44(13) . . ? C7 C17 H17A 116.8 . . ? C14 C17 H17A 116.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.9(4) . . . . ? C1 Cl1 N11 O12 -174.6(16) . . . . ? O12 Cl1 N11 O11 -172.9(4) . . . . ? C1 Cl1 N11 O11 12.5(18) . . . . ? O11 Cl1 N11 C1 -12.5(18) . . . . ? O12 Cl1 N11 C1 174.6(16) . . . . ? O12 Cl1 O11 N11 132(3) . . . . ? C1 Cl1 O11 N11 -4.2(6) . . . . ? O12 N11 O11 Cl1 -8.4(5) . . . . ? C1 N11 O11 Cl1 173.5(9) . . . . ? O11 N11 O12 Cl1 5.0(3) . . . . ? C1 N11 O12 Cl1 -177.1(8) . . . . ? O11 Cl1 O12 N11 -135(2) . . . . ? C1 Cl1 O12 N11 1.8(5) . . . . ? Cl1 N11 C1 C6 9.2(16) . . . . ? O12 N11 C1 C6 -177.1(3) . . . . ? O11 N11 C1 C6 1.0(5) . . . . ? Cl1 N11 C1 C2 -171.8(14) . . . . ? O12 N11 C1 C2 2.0(4) . . . . ? O11 N11 C1 C2 -180.0(3) . . . . ? O12 N11 C1 Cl1 173.7(18) . . . . ? O11 N11 C1 Cl1 -8.2(12) . . . . ? O11 Cl1 C1 N11 168.9(16) . . . . ? O12 Cl1 C1 N11 -4.9(14) . . . . ? N11 Cl1 C1 C6 -171.5(15) . . . . ? O11 Cl1 C1 C6 -2.6(3) . . . . ? O12 Cl1 C1 C6 -176.45(13) . . . . ? N11 Cl1 C1 C2 8.9(15) . . . . ? O11 Cl1 C1 C2 177.9(3) . . . . ? O12 Cl1 C1 C2 4.00(17) . . . . ? N11 C1 C2 C3 -179.3(2) . . . . ? C6 C1 C2 C3 -0.23(16) . . . . ? Cl1 C1 C2 C3 179.29(10) . . . . ? C1 C2 C3 C4 0.27(16) . . . . ? C2 C3 C4 C5 -0.43(15) . . . . ? C2 C3 C4 C7 179.97(9) . . . . ? C3 C4 C5 C6 0.56(15) . . . . ? C7 C4 C5 C6 -179.82(9) . . . . ? C4 C5 C6 C1 -0.53(16) . . . . ? N11 C1 C6 C5 179.3(2) . . . . ? C2 C1 C6 C5 0.36(16) . . . . ? Cl1 C1 C6 C5 -179.21(10) . . . . ? C5 C4 C7 C17 175.69(13) . . . . ? C3 C4 C7 C17 -4.71(19) . . . . ? O1 Cl11 N1 O2 -172.9(4) . . . . ? C11 Cl11 N1 O2 174.6(16) . . . . ? O2 Cl11 N1 O1 172.9(4) . . . . ? C11 Cl11 N1 O1 -12.5(18) . . . . ? O1 Cl11 N1 C11 12.5(18) . . . . ? O2 Cl11 N1 C11 -174.6(16) . . . . ? O2 Cl11 O1 N1 -132(3) . . . . ? C11 Cl11 O1 N1 4.2(6) . . . . ? O2 N1 O1 Cl11 8.4(5) . . . . ? C11 N1 O1 Cl11 -173.5(9) . . . . ? O1 N1 O2 Cl11 -5.0(3) . . . . ? C11 N1 O2 Cl11 177.1(8) . . . . ? O1 Cl11 O2 N1 135(2) . . . . ? C11 Cl11 O2 N1 -1.8(5) . . . . ? Cl11 N1 C11 C16 -9.2(16) . . . . ? O2 N1 C11 C16 177.1(3) . . . . ? O1 N1 C11 C16 -1.0(5) . . . . ? Cl11 N1 C11 C12 171.8(14) . . . . ? O2 N1 C11 C12 -2.0(4) . . . . ? O1 N1 C11 C12 180.0(3) . . . . ? O2 N1 C11 Cl11 -173.7(18) . . . . ? O1 N1 C11 Cl11 8.2(12) . . . . ? O1 Cl11 C11 N1 -168.9(16) . . . . ? O2 Cl11 C11 N1 4.9(14) . . . . ? N1 Cl11 C11 C16 171.5(15) . . . . ? O1 Cl11 C11 C16 2.6(3) . . . . ? O2 Cl11 C11 C16 176.45(13) . . . . ? N1 Cl11 C11 C12 -8.9(15) . . . . ? O1 Cl11 C11 C12 -177.9(3) . . . . ? O2 Cl11 C11 C12 -4.00(17) . . . . ? N1 C11 C12 C13 179.3(2) . . . . ? C16 C11 C12 C13 0.23(16) . . . . ? Cl11 C11 C12 C13 -179.29(10) . . . . ? C11 C12 C13 C14 -0.27(16) . . . . ? C12 C13 C14 C15 0.43(15) . . . . ? C12 C13 C14 C17 -179.97(9) . . . . ? C13 C14 C15 C16 -0.56(15) . . . . ? C17 C14 C15 C16 179.82(9) . . . . ? C14 C15 C16 C11 0.53(16) . . . . ? N1 C11 C16 C15 -179.3(2) . . . . ? C12 C11 C16 C15 -0.36(16) . . . . ? Cl11 C11 C16 C15 179.21(10) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.69(13) . . . . ? C13 C14 C17 C7 4.71(19) . . . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 27.81 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.097 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.037 # start Validation Reply Form _vrf_SYMMG02_CNS-DMSOII-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-DMSOII-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.94 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:27. ; # end Validation Reply Form #===END data_CNS-DMSOII-big-A1 _database_code_depnum_ccdc_archive 'CCDC 761237' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'A 1' _symmetry_space_group_name_Hall 'A 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, y+1/2, z+1/2' _cell_length_a 3.91730(10) _cell_length_b 25.9126(3) _cell_length_c 24.4686(3) _cell_angle_alpha 90.0000(10) _cell_angle_beta 93.1510(10) _cell_angle_gamma 90.0000(10) _cell_volume 2479.99(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26637 _cell_measurement_theta_min 2.622 _cell_measurement_theta_max 26.246 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.907836 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11076 _diffrn_reflns_av_R_equivalents 0.0159 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.84 _reflns_number_total 8076 _reflns_number_gt 3667 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+1.4019P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00081(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(2) _refine_ls_number_reflns 8076 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1131 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1496 _refine_ls_wR_factor_gt 0.1222 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1A Cl 0.3704 -0.2305 -0.0879 0.1114(3) Uani 0.49(5) 1 d P A 1 N1A N -0.3627 0.2077 0.0861 0.0806(5) Uani 0.49(5) 1 d P A 1 O1A O -0.3165 0.2487 0.0615 0.1291(8) Uani 0.49(5) 1 d P A 1 O2A O -0.4981 0.2064 0.1290 0.1116(5) Uani 0.49(5) 1 d P A 1 Cl1E Cl -0.3704 0.2305 0.0879 0.1114(3) Uani 0.51(5) 1 d P A 2 N1E N 0.3627 -0.2077 -0.0861 0.0806(5) Uani 0.51(5) 1 d P A 2 O1E O 0.3165 -0.2487 -0.0615 0.1291(8) Uani 0.51(5) 1 d P A 2 O2E O 0.4981 -0.2064 -0.1290 0.1116(5) Uani 0.51(5) 1 d P A 2 C1A C 0.2613 -0.1648 -0.0616 0.0723(2) Uani 1 1 d . A 2 C2A C 0.3150 -0.1195 -0.0897 0.0788(3) Uani 1 1 d . A 2 H2A H 0.4125 -0.1203 -0.1235 0.095 Uiso 1 1 calc R A 2 C3A C 0.2229 -0.0737 -0.0671 0.0749(2) Uani 1 1 d . A 2 H3A H 0.2576 -0.0432 -0.0861 0.090 Uiso 1 1 calc R A 2 C4A C 0.0781 -0.0717 -0.0165 0.0639(2) Uani 1 1 d . A 2 C5A C 0.0280 -0.1181 0.0104 0.0712(2) Uani 1 1 d . A 2 H5A H -0.0702 -0.1176 0.0441 0.085 Uiso 1 1 calc R A 2 C6A C 0.1188 -0.1646 -0.0113 0.0750(2) Uani 1 1 d . A 2 H6A H 0.0849 -0.1953 0.0074 0.090 Uiso 1 1 calc R A 2 C7A C -0.0241 -0.0234 0.0092 0.0705(2) Uani 1 1 d . A 2 H7A H -0.1341 -0.0262 0.0418 0.085 Uiso 1 1 calc R A 2 C11A C -0.2613 0.1648 0.0615 0.0723(2) Uani 1 1 d . A 2 C12A C -0.3150 0.1195 0.0897 0.0788(3) Uani 1 1 d . A 2 H12A H -0.4125 0.1203 0.1235 0.095 Uiso 1 1 calc R A 2 C13A C -0.2229 0.0737 0.0671 0.0749(2) Uani 1 1 d . A 2 H13A H -0.2576 0.0432 0.0860 0.090 Uiso 1 1 calc R A 2 C14A C -0.0781 0.0717 0.0164 0.0639(2) Uani 1 1 d . A 2 C15A C -0.0280 0.1181 -0.0104 0.0712(2) Uani 1 1 d . A 2 H15A H 0.0702 0.1176 -0.0441 0.085 Uiso 1 1 calc R A 2 C16A C -0.1188 0.1646 0.0113 0.0750(2) Uani 1 1 d . A 2 H16A H -0.0848 0.1953 -0.0074 0.090 Uiso 1 1 calc R A 2 C17A C 0.0241 0.0233 -0.0092 0.0705(2) Uani 1 1 d . A 2 H17A H 0.1342 0.0261 -0.0418 0.085 Uiso 1 1 calc R A 2 Cl1B Cl 0.3704 -0.2305 0.4121 0.1114(3) Uani 0.49(5) 1 d P B 3 N1B N -0.3627 0.2077 0.5861 0.0806(5) Uani 0.49(5) 1 d P B 3 O1B O -0.3165 0.2487 0.5615 0.1291(8) Uani 0.49(5) 1 d P B 3 O2B O -0.4981 0.2064 0.6290 0.1116(5) Uani 0.49(5) 1 d P B 3 Cl1F Cl -0.3704 0.2305 0.5879 0.1114(3) Uani 0.51(5) 1 d P B 4 N1F N 0.3627 -0.2077 0.4139 0.0806(5) Uani 0.51(5) 1 d P B 4 O1F O 0.3165 -0.2487 0.4385 0.1291(8) Uani 0.51(5) 1 d P B 4 O2F O 0.4981 -0.2064 0.3710 0.1116(5) Uani 0.51(5) 1 d P B 4 C1B C 0.2613 -0.1648 0.4384 0.0723(2) Uani 1 1 d . B 4 C2B C 0.3150 -0.1195 0.4103 0.0788(3) Uani 1 1 d . B 4 H2B H 0.4125 -0.1203 0.3765 0.095 Uiso 1 1 calc R B 4 C3B C 0.2229 -0.0737 0.4329 0.0749(2) Uani 1 1 d . B 4 H3B H 0.2576 -0.0432 0.4139 0.090 Uiso 1 1 calc R B 4 C4B C 0.0781 -0.0717 0.4835 0.0639(2) Uani 1 1 d . B 4 C5B C 0.0280 -0.1181 0.5104 0.0712(2) Uani 1 1 d . B 4 H5B H -0.0702 -0.1176 0.5441 0.085 Uiso 1 1 calc R B 4 C6B C 0.1188 -0.1646 0.4887 0.0750(2) Uani 1 1 d . B 4 H6B H 0.0849 -0.1953 0.5074 0.090 Uiso 1 1 calc R B 4 C7B C -0.0241 -0.0234 0.5092 0.0705(2) Uani 1 1 d . B 4 H7B H -0.1341 -0.0262 0.5418 0.085 Uiso 1 1 calc R B 4 C11B C -0.2613 0.1648 0.5615 0.0723(2) Uani 1 1 d . B 4 C12B C -0.3150 0.1195 0.5897 0.0788(3) Uani 1 1 d . B 4 H12B H -0.4125 0.1203 0.6235 0.095 Uiso 1 1 calc R B 4 C13B C -0.2229 0.0737 0.5671 0.0749(2) Uani 1 1 d . B 4 H13B H -0.2576 0.0432 0.5860 0.090 Uiso 1 1 calc R B 4 C14B C -0.0781 0.0717 0.5164 0.0639(2) Uani 1 1 d . B 4 C15B C -0.0280 0.1181 0.4896 0.0712(2) Uani 1 1 d . B 4 H15B H 0.0702 0.1176 0.4559 0.085 Uiso 1 1 calc R B 4 C16B C -0.1188 0.1646 0.5113 0.0750(2) Uani 1 1 d . B 4 H16B H -0.0848 0.1953 0.4926 0.090 Uiso 1 1 calc R B 4 C17B C 0.0241 0.0233 0.4908 0.0705(2) Uani 1 1 d . B 4 H17B H 0.1342 0.0261 0.4582 0.085 Uiso 1 1 calc R B 4 Cl1C Cl -0.3704 0.0195 0.3379 0.1114(3) Uani 0.443(3) 1 d P C 5 N1C N 0.3627 0.4577 0.1639 0.0806(5) Uani 0.443(3) 1 d P C 5 O1C O 0.3165 0.4987 0.1885 0.1291(8) Uani 0.443(3) 1 d P C 5 O2C O 0.4981 0.4564 0.1210 0.1116(5) Uani 0.443(3) 1 d P C 5 Cl1G Cl 0.3704 0.4805 0.1621 0.1114(3) Uani 0.557(3) 1 d P C 6 N1G N -0.3627 0.0423 0.3361 0.0806(5) Uani 0.557(3) 1 d P C 6 O1G O -0.3165 0.0013 0.3115 0.1291(8) Uani 0.557(3) 1 d P C 6 O2G O -0.4981 0.0436 0.3790 0.1116(5) Uani 0.557(3) 1 d P C 6 C1C C -0.2613 0.0852 0.3115 0.0723(2) Uani 1 1 d . C 6 C2C C -0.3150 0.1305 0.3397 0.0788(3) Uani 1 1 d . C 6 H2C H -0.4125 0.1297 0.3735 0.095 Uiso 1 1 calc R C 6 C3C C -0.2229 0.1763 0.3171 0.0749(2) Uani 1 1 d . C 6 H3C H -0.2576 0.2068 0.3360 0.090 Uiso 1 1 calc R C 6 C4C C -0.0781 0.1783 0.2664 0.0639(2) Uani 1 1 d . C 6 C5C C -0.0280 0.1319 0.2396 0.0712(2) Uani 1 1 d . C 6 H5C H 0.0702 0.1324 0.2059 0.085 Uiso 1 1 calc R C 6 C6C C -0.1188 0.0854 0.2613 0.0750(2) Uani 1 1 d . C 6 H6C H -0.0848 0.0547 0.2426 0.090 Uiso 1 1 calc R C 6 C7C C 0.0241 0.2267 0.2408 0.0705(2) Uani 1 1 d . C 6 H7C H 0.1342 0.2239 0.2082 0.085 Uiso 1 1 calc R C 6 C11C C 0.2613 0.4148 0.1885 0.0723(2) Uani 1 1 d . C 6 C12C C 0.3150 0.3695 0.1603 0.0788(3) Uani 1 1 d . C 6 H12C H 0.4125 0.3703 0.1265 0.095 Uiso 1 1 calc R C 6 C13C C 0.2229 0.3237 0.1829 0.0749(2) Uani 1 1 d . C 6 H13C H 0.2577 0.2932 0.1640 0.090 Uiso 1 1 calc R C 6 C14C C 0.0781 0.3217 0.2335 0.0639(2) Uani 1 1 d . C 6 C15C C 0.0280 0.3681 0.2604 0.0712(2) Uani 1 1 d . C 6 H15C H -0.0702 0.3676 0.2941 0.085 Uiso 1 1 calc R C 6 C16C C 0.1188 0.4146 0.2387 0.0750(2) Uani 1 1 d . C 6 H16C H 0.0849 0.4452 0.2574 0.090 Uiso 1 1 calc R C 6 C17C C -0.0241 0.2733 0.2592 0.0705(2) Uani 1 1 d . C 6 H17C H -0.1341 0.2761 0.2918 0.085 Uiso 1 1 calc R C 6 Cl1D Cl -0.3704 0.0195 -0.1621 0.1114(3) Uani 0.405(3) 1 d P D 7 N1D N 0.3627 0.4577 -0.3361 0.0806(5) Uani 0.405(3) 1 d P D 7 O1D O 0.3165 0.4987 -0.3115 0.1291(8) Uani 0.405(3) 1 d P D 7 O2D O 0.4981 0.4564 -0.3790 0.1116(5) Uani 0.405(3) 1 d P D 7 Cl1H Cl 0.3704 0.4805 -0.3379 0.1114(3) Uani 0.595(3) 1 d P D 8 N1H N -0.3627 0.0423 -0.1639 0.0806(5) Uani 0.595(3) 1 d P D 8 O1H O -0.3165 0.0013 -0.1885 0.1291(8) Uani 0.595(3) 1 d P D 8 O2H O -0.4981 0.0436 -0.1210 0.1116(5) Uani 0.595(3) 1 d P D 8 C1D C -0.2613 0.0852 -0.1885 0.0723(2) Uani 1 1 d . D 8 C2D C -0.3150 0.1305 -0.1603 0.0788(3) Uani 1 1 d . D 8 H2D H -0.4125 0.1297 -0.1265 0.095 Uiso 1 1 calc R D 8 C3D C -0.2229 0.1763 -0.1829 0.0749(2) Uani 1 1 d . D 8 H3D H -0.2576 0.2068 -0.1640 0.090 Uiso 1 1 calc R D 8 C4D C -0.0781 0.1783 -0.2336 0.0639(2) Uani 1 1 d . D 8 C5D C -0.0280 0.1319 -0.2604 0.0712(2) Uani 1 1 d . D 8 H5D H 0.0702 0.1324 -0.2941 0.085 Uiso 1 1 calc R D 8 C6D C -0.1188 0.0854 -0.2387 0.0750(2) Uani 1 1 d . D 8 H6D H -0.0848 0.0547 -0.2574 0.090 Uiso 1 1 calc R D 8 C7D C 0.0241 0.2267 -0.2592 0.0705(2) Uani 1 1 d . D 8 H7D H 0.1342 0.2239 -0.2918 0.085 Uiso 1 1 calc R D 8 C11D C 0.2613 0.4148 -0.3115 0.0723(2) Uani 1 1 d . D 8 C12D C 0.3150 0.3695 -0.3397 0.0788(3) Uani 1 1 d . D 8 H12D H 0.4125 0.3703 -0.3735 0.095 Uiso 1 1 calc R D 8 C13D C 0.2229 0.3237 -0.3171 0.0749(2) Uani 1 1 d . D 8 H13D H 0.2577 0.2932 -0.3360 0.090 Uiso 1 1 calc R D 8 C14D C 0.0781 0.3217 -0.2665 0.0639(2) Uani 1 1 d . D 8 C15D C 0.0280 0.3681 -0.2396 0.0712(2) Uani 1 1 d . D 8 H15D H -0.0702 0.3676 -0.2059 0.085 Uiso 1 1 calc R D 8 C16D C 0.1188 0.4146 -0.2613 0.0750(2) Uani 1 1 d . D 8 H16D H 0.0849 0.4452 -0.2426 0.090 Uiso 1 1 calc R D 8 C17D C -0.0241 0.2733 -0.2408 0.0705(2) Uani 1 1 d . D 8 H17D H -0.1341 0.2761 -0.2082 0.085 Uiso 1 1 calc R D 8 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1A 0.1107(5) 0.0912(6) 0.1319(7) -0.0468(5) 0.0034(4) 0.0251(4) N1A 0.0776(11) 0.0656(12) 0.0979(13) -0.0038(9) -0.0034(9) 0.0069(7) O1A 0.1658(16) 0.0770(10) 0.1476(17) 0.0097(11) 0.0364(12) 0.0136(10) O2A 0.1486(14) 0.0937(10) 0.0954(10) -0.0248(8) 0.0332(10) 0.0183(9) Cl1E 0.1107(5) 0.0912(6) 0.1319(7) -0.0468(5) 0.0034(4) 0.0251(4) N1E 0.0776(11) 0.0656(12) 0.0979(13) -0.0038(9) -0.0034(9) 0.0069(7) O1E 0.1658(16) 0.0770(10) 0.1476(17) 0.0097(11) 0.0364(12) 0.0136(10) O2E 0.1486(14) 0.0937(10) 0.0954(10) -0.0248(8) 0.0332(10) 0.0183(9) C1A 0.0562(5) 0.0859(6) 0.0741(5) -0.0158(4) -0.0023(4) 0.0061(4) C2A 0.0674(5) 0.1057(7) 0.0640(5) -0.0035(5) 0.0092(4) -0.0005(5) C3A 0.0673(5) 0.0843(6) 0.0734(6) 0.0086(4) 0.0067(4) -0.0037(4) C4A 0.0494(4) 0.0777(5) 0.0645(5) -0.0022(4) 0.0007(3) -0.0018(4) C5A 0.0660(5) 0.0841(6) 0.0638(5) 0.0010(4) 0.0082(4) -0.0005(4) C6A 0.0712(5) 0.0778(6) 0.0761(6) 0.0030(4) 0.0050(4) 0.0018(4) C7A 0.0597(5) 0.0824(5) 0.0698(5) 0.0034(4) 0.0067(4) -0.0025(4) C11A 0.0562(5) 0.0859(6) 0.0741(5) -0.0158(4) -0.0023(4) 0.0061(4) C12A 0.0674(5) 0.1057(7) 0.0640(5) -0.0035(5) 0.0092(4) -0.0005(5) C13A 0.0673(5) 0.0843(6) 0.0734(6) 0.0086(4) 0.0067(4) -0.0037(4) C14A 0.0494(4) 0.0777(5) 0.0645(5) -0.0022(4) 0.0007(3) -0.0018(4) C15A 0.0660(5) 0.0841(6) 0.0638(5) 0.0010(4) 0.0082(4) -0.0005(4) C16A 0.0712(5) 0.0778(6) 0.0761(6) 0.0030(4) 0.0050(4) 0.0018(4) C17A 0.0597(5) 0.0824(5) 0.0698(5) 0.0034(4) 0.0067(4) -0.0025(4) Cl1B 0.1107(5) 0.0912(6) 0.1319(7) -0.0468(5) 0.0034(4) 0.0251(4) N1B 0.0776(11) 0.0656(12) 0.0979(13) -0.0038(9) -0.0034(9) 0.0069(7) O1B 0.1658(16) 0.0770(10) 0.1476(17) 0.0097(11) 0.0364(12) 0.0136(10) O2B 0.1486(14) 0.0937(10) 0.0954(10) -0.0248(8) 0.0332(10) 0.0183(9) Cl1F 0.1107(5) 0.0912(6) 0.1319(7) -0.0468(5) 0.0034(4) 0.0251(4) N1F 0.0776(11) 0.0656(12) 0.0979(13) -0.0038(9) -0.0034(9) 0.0069(7) O1F 0.1658(16) 0.0770(10) 0.1476(17) 0.0097(11) 0.0364(12) 0.0136(10) O2F 0.1486(14) 0.0937(10) 0.0954(10) -0.0248(8) 0.0332(10) 0.0183(9) C1B 0.0562(5) 0.0859(6) 0.0741(5) -0.0158(4) -0.0023(4) 0.0061(4) C2B 0.0674(5) 0.1057(7) 0.0640(5) -0.0035(5) 0.0092(4) -0.0005(5) C3B 0.0673(5) 0.0843(6) 0.0734(6) 0.0086(4) 0.0067(4) -0.0037(4) C4B 0.0494(4) 0.0777(5) 0.0645(5) -0.0022(4) 0.0007(3) -0.0018(4) C5B 0.0660(5) 0.0841(6) 0.0638(5) 0.0010(4) 0.0082(4) -0.0005(4) C6B 0.0712(5) 0.0778(6) 0.0761(6) 0.0030(4) 0.0050(4) 0.0018(4) C7B 0.0597(5) 0.0824(5) 0.0698(5) 0.0034(4) 0.0067(4) -0.0025(4) C11B 0.0562(5) 0.0859(6) 0.0741(5) -0.0158(4) -0.0023(4) 0.0061(4) C12B 0.0674(5) 0.1057(7) 0.0640(5) -0.0035(5) 0.0092(4) -0.0005(5) C13B 0.0673(5) 0.0843(6) 0.0734(6) 0.0086(4) 0.0067(4) -0.0037(4) C14B 0.0494(4) 0.0777(5) 0.0645(5) -0.0022(4) 0.0007(3) -0.0018(4) C15B 0.0660(5) 0.0841(6) 0.0638(5) 0.0010(4) 0.0082(4) -0.0005(4) C16B 0.0712(5) 0.0778(6) 0.0761(6) 0.0030(4) 0.0050(4) 0.0018(4) C17B 0.0597(5) 0.0824(5) 0.0698(5) 0.0034(4) 0.0067(4) -0.0025(4) Cl1C 0.1107(5) 0.0912(6) 0.1319(7) 0.0468(5) 0.0034(4) -0.0251(4) N1C 0.0776(11) 0.0656(12) 0.0979(13) 0.0038(9) -0.0034(9) -0.0069(7) O1C 0.1658(16) 0.0770(10) 0.1476(17) -0.0097(11) 0.0364(12) -0.0136(10) O2C 0.1486(14) 0.0937(10) 0.0954(10) 0.0248(8) 0.0332(10) -0.0183(9) Cl1G 0.1107(5) 0.0912(6) 0.1319(7) 0.0468(5) 0.0034(4) -0.0251(4) N1G 0.0776(11) 0.0656(12) 0.0979(13) 0.0038(9) -0.0034(9) -0.0069(7) O1G 0.1658(16) 0.0770(10) 0.1476(17) -0.0097(11) 0.0364(12) -0.0136(10) O2G 0.1486(14) 0.0937(10) 0.0954(10) 0.0248(8) 0.0332(10) -0.0183(9) C1C 0.0562(5) 0.0859(6) 0.0741(5) 0.0158(4) -0.0023(4) -0.0061(4) C2C 0.0674(5) 0.1057(7) 0.0640(5) 0.0035(5) 0.0092(4) 0.0005(5) C3C 0.0673(5) 0.0843(6) 0.0734(6) -0.0086(4) 0.0067(4) 0.0037(4) C4C 0.0494(4) 0.0777(5) 0.0645(5) 0.0022(4) 0.0007(3) 0.0018(4) C5C 0.0660(5) 0.0841(6) 0.0638(5) -0.0010(4) 0.0082(4) 0.0005(4) C6C 0.0712(5) 0.0778(6) 0.0761(6) -0.0030(4) 0.0050(4) -0.0018(4) C7C 0.0597(5) 0.0824(5) 0.0698(5) -0.0034(4) 0.0067(4) 0.0025(4) C11C 0.0562(5) 0.0859(6) 0.0741(5) 0.0158(4) -0.0023(4) -0.0061(4) C12C 0.0674(5) 0.1057(7) 0.0640(5) 0.0035(5) 0.0092(4) 0.0005(5) C13C 0.0673(5) 0.0843(6) 0.0734(6) -0.0086(4) 0.0067(4) 0.0037(4) C14C 0.0494(4) 0.0777(5) 0.0645(5) 0.0022(4) 0.0007(3) 0.0018(4) C15C 0.0660(5) 0.0841(6) 0.0638(5) -0.0010(4) 0.0082(4) 0.0005(4) C16C 0.0712(5) 0.0778(6) 0.0761(6) -0.0030(4) 0.0050(4) -0.0018(4) C17C 0.0597(5) 0.0824(5) 0.0698(5) -0.0034(4) 0.0067(4) 0.0025(4) Cl1D 0.1107(5) 0.0912(6) 0.1319(7) 0.0468(5) 0.0034(4) -0.0251(4) N1D 0.0776(11) 0.0656(12) 0.0979(13) 0.0038(9) -0.0034(9) -0.0069(7) O1D 0.1658(16) 0.0770(10) 0.1476(17) -0.0097(11) 0.0364(12) -0.0136(10) O2D 0.1486(14) 0.0937(10) 0.0954(10) 0.0248(8) 0.0332(10) -0.0183(9) Cl1H 0.1107(5) 0.0912(6) 0.1319(7) 0.0468(5) 0.0034(4) -0.0251(4) N1H 0.0776(11) 0.0656(12) 0.0979(13) 0.0038(9) -0.0034(9) -0.0069(7) O1H 0.1658(16) 0.0770(10) 0.1476(17) -0.0097(11) 0.0364(12) -0.0136(10) O2H 0.1486(14) 0.0937(10) 0.0954(10) 0.0248(8) 0.0332(10) -0.0183(9) C1D 0.0562(5) 0.0859(6) 0.0741(5) 0.0158(4) -0.0023(4) -0.0061(4) C2D 0.0674(5) 0.1057(7) 0.0640(5) 0.0035(5) 0.0092(4) 0.0005(5) C3D 0.0673(5) 0.0843(6) 0.0734(6) -0.0086(4) 0.0067(4) 0.0037(4) C4D 0.0494(4) 0.0777(5) 0.0645(5) 0.0022(4) 0.0007(3) 0.0018(4) C5D 0.0660(5) 0.0841(6) 0.0638(5) -0.0010(4) 0.0082(4) 0.0005(4) C6D 0.0712(5) 0.0778(6) 0.0761(6) -0.0030(4) 0.0050(4) -0.0018(4) C7D 0.0597(5) 0.0824(5) 0.0698(5) -0.0034(4) 0.0067(4) 0.0025(4) C11D 0.0562(5) 0.0859(6) 0.0741(5) 0.0158(4) -0.0023(4) -0.0061(4) C12D 0.0674(5) 0.1057(7) 0.0640(5) 0.0035(5) 0.0092(4) 0.0005(5) C13D 0.0673(5) 0.0843(6) 0.0734(6) -0.0086(4) 0.0067(4) 0.0037(4) C14D 0.0494(4) 0.0777(5) 0.0645(5) 0.0022(4) 0.0007(3) 0.0018(4) C15D 0.0660(5) 0.0841(6) 0.0638(5) -0.0010(4) 0.0082(4) 0.0005(4) C16D 0.0712(5) 0.0778(6) 0.0761(6) -0.0030(4) 0.0050(4) -0.0018(4) C17D 0.0597(5) 0.0824(5) 0.0698(5) -0.0034(4) 0.0067(4) 0.0025(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1A O2A 1.2038 . ? N1A O1A 1.2373 . ? Cl1E C11A 1.8770 . ? N1E O2E 1.2035 . ? N1E O1E 1.2370 . ? N1E C1A 1.3354 . ? C1A C6A 1.3774 . ? C1A C2A 1.3816 . ? C2A C3A 1.3660 . ? C2A H2A 0.9300 . ? C3A C4A 1.3927 . ? C3A H3A 0.9300 . ? C4A C5A 1.3889 . ? C4A C7A 1.4662 . ? C5A C6A 1.3723 . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? C7A C17A 1.3087 . ? C7A H7A 0.9300 . ? C11A C16A 1.3769 . ? C11A C12A 1.3819 . ? C12A C13A 1.3661 . ? C12A H12A 0.9300 . ? C13A C14A 1.3931 . ? C13A H13A 0.9300 . ? C14A C15A 1.3888 . ? C14A C17A 1.4663 . ? C15A C16A 1.3724 . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? C17A H17A 0.9300 . ? N1B O2B 1.2038 . ? N1B O1B 1.2373 . ? Cl1F C11B 1.8770 . ? N1F O2F 1.2035 . ? N1F O1F 1.2370 . ? N1F C1B 1.3354 . ? C1B C6B 1.3774 . ? C1B C2B 1.3816 . ? C2B C3B 1.3660 . ? C2B H2B 0.9300 . ? C3B C4B 1.3927 . ? C3B H3B 0.9300 . ? C4B C5B 1.3889 . ? C4B C7B 1.4662 . ? C5B C6B 1.3723 . ? C5B H5B 0.9300 . ? C6B H6B 0.9300 . ? C7B C17B 1.3087 . ? C7B H7B 0.9300 . ? C11B C16B 1.3769 . ? C11B C12B 1.3819 . ? C12B C13B 1.3661 . ? C12B H12B 0.9300 . ? C13B C14B 1.3931 . ? C13B H13B 0.9300 . ? C14B C15B 1.3888 . ? C14B C17B 1.4663 . ? C15B C16B 1.3724 . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? C17B H17B 0.9300 . ? N1C O2C 1.2038 . ? N1C O1C 1.2373 . ? Cl1G C11C 1.8772 . ? N1G O2G 1.2038 . ? N1G O1G 1.2370 . ? N1G C1C 1.3355 . ? C1C C6C 1.3769 . ? C1C C2C 1.3818 . ? C2C C3C 1.3661 . ? C2C H2C 0.9300 . ? C3C C4C 1.3931 . ? C3C H3C 0.9300 . ? C4C C5C 1.3888 . ? C4C C7C 1.4663 . ? C5C C6C 1.3725 . ? C5C H5C 0.9300 . ? C6C H6C 0.9300 . ? C7C C17C 1.3079 . ? C7C H7C 0.9300 . ? C11C C16C 1.3769 . ? C11C C12C 1.3817 . ? C12C C13C 1.3661 . ? C12C H12C 0.9300 . ? C13C C14C 1.3922 . ? C13C H13C 0.9300 . ? C14C C15C 1.3888 . ? C14C C17C 1.4671 . ? C15C C16C 1.3717 . ? C15C H15C 0.9300 . ? C16C H16C 0.9300 . ? C17C H17C 0.9300 . ? N1D O2D 1.2038 . ? N1D O1D 1.2373 . ? Cl1H C11D 1.8772 . ? N1H O2H 1.2038 . ? N1H O1H 1.2370 . ? N1H C1D 1.3355 . ? C1D C6D 1.3769 . ? C1D C2D 1.3818 . ? C2D C3D 1.3661 . ? C2D H2D 0.9300 . ? C3D C4D 1.3931 . ? C3D H3D 0.9300 . ? C4D C5D 1.3888 . ? C4D C7D 1.4663 . ? C5D C6D 1.3725 . ? C5D H5D 0.9300 . ? C6D H6D 0.9300 . ? C7D C17D 1.3079 . ? C7D H7D 0.9300 . ? C11D C16D 1.3769 . ? C11D C12D 1.3817 . ? C12D C13D 1.3661 . ? C12D H12D 0.9300 . ? C13D C14D 1.3922 . ? C13D H13D 0.9300 . ? C14D C15D 1.3888 . ? C14D C17D 1.4671 . ? C15D C16D 1.3717 . ? C15D H15D 0.9300 . ? C16D H16D 0.9300 . ? C17D H17D 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2A N1A O1A 122.159(1) . . ? O2E N1E O1E 122.136(1) . . ? O2E N1E C1A 121.670(1) . . ? O1E N1E C1A 116.174(2) . . ? N1E C1A C6A 123.309(1) . . ? N1E C1A C2A 115.243(2) . . ? C6A C1A C2A 121.437(3) . . ? C3A C2A C1A 119.093(1) . . ? C3A C2A H2A 120.5 . . ? C1A C2A H2A 120.5 . . ? C2A C3A C4A 121.459(1) . . ? C2A C3A H3A 119.3 . . ? C4A C3A H3A 119.3 . . ? C5A C4A C3A 117.556(2) . . ? C5A C4A C7A 119.193(1) . . ? C3A C4A C7A 123.249(1) . . ? C6A C5A C4A 122.140(2) . . ? C6A C5A H5A 118.9 . . ? C4A C5A H5A 118.9 . . ? C5A C6A C1A 118.311(2) . . ? C5A C6A H6A 120.8 . . ? C1A C6A H6A 120.8 . . ? C17A C7A C4A 126.406(1) . . ? C17A C7A H7A 116.8 . . ? C4A C7A H7A 116.8 . . ? C16A C11A C12A 121.449(1) . . ? C16A C11A Cl1E 114.864(2) . . ? C12A C11A Cl1E 123.7 . . ? C13A C12A C11A 119.067(1) . . ? C13A C12A H12A 120.5 . . ? C11A C12A H12A 120.5 . . ? C12A C13A C14A 121.466(1) . . ? C12A C13A H13A 119.3 . . ? C14A C13A H13A 119.3 . . ? C15A C14A C13A 117.552(1) . . ? C15A C14A C17A 119.243(1) . . ? C13A C14A C17A 123.203(1) . . ? C16A C15A C14A 122.130(1) . . ? C16A C15A H15A 118.9 . . ? C14A C15A H15A 118.9 . . ? C15A C16A C11A 118.332(1) . . ? C15A C16A H16A 120.8 . . ? C11A C16A H16A 120.8 . . ? C7A C17A C14A 126.445(1) . . ? C7A C17A H17A 116.8 . . ? C14A C17A H17A 116.8 . . ? O2B N1B O1B 122.159(2) . . ? O2F N1F O1F 122.136(2) . . ? O2F N1F C1B 121.670(2) . . ? O1F N1F C1B 116.174(2) . . ? N1F C1B C6B 123.309(2) . . ? N1F C1B C2B 115.243(1) . . ? C6B C1B C2B 121.437(1) . . ? C3B C2B C1B 119.093(1) . . ? C3B C2B H2B 120.5 . . ? C1B C2B H2B 120.5 . . ? C2B C3B C4B 121.459(2) . . ? C2B C3B H3B 119.3 . . ? C4B C3B H3B 119.3 . . ? C5B C4B C3B 117.556(1) . . ? C5B C4B C7B 119.193(1) . . ? C3B C4B C7B 123.249(2) . . ? C6B C5B C4B 122.140(1) . . ? C6B C5B H5B 118.9 . . ? C4B C5B H5B 118.9 . . ? C5B C6B C1B 118.311(1) . . ? C5B C6B H6B 120.8 . . ? C1B C6B H6B 120.8 . . ? C17B C7B C4B 126.406(1) . . ? C17B C7B H7B 116.8 . . ? C4B C7B H7B 116.8 . . ? C16B C11B C12B 121.449(1) . . ? C16B C11B Cl1F 114.864(1) . . ? C12B C11B Cl1F 123.685(1) . . ? C13B C12B C11B 119.067(1) . . ? C13B C12B H12B 120.5 . . ? C11B C12B H12B 120.5 . . ? C12B C13B C14B 121.466(1) . . ? C12B C13B H13B 119.3 . . ? C14B C13B H13B 119.3 . . ? C15B C14B C13B 117.552(1) . . ? C15B C14B C17B 119.243(1) . . ? C13B C14B C17B 123.203(1) . . ? C16B C15B C14B 122.130(1) . . ? C16B C15B H15B 118.9 . . ? C14B C15B H15B 118.9 . . ? C15B C16B C11B 118.332(1) . . ? C15B C16B H16B 120.8 . . ? C11B C16B H16B 120.8 . . ? C7B C17B C14B 126.4 . . ? C7B C17B H17B 116.8 . . ? C14B C17B H17B 116.8 . . ? O2C N1C O1C 122.161(1) . . ? O2G N1G O1G 122.140(1) . . ? O2G N1G C1C 121.676(1) . . ? O1G N1G C1C 116.163(1) . . ? N1G C1C C6C 123.317(1) . . ? N1G C1C C2C 115.221(2) . . ? C6C C1C C2C 121.452(1) . . ? C3C C2C C1C 119.065(1) . . ? C3C C2C H2C 120.5 . . ? C1C C2C H2C 120.5 . . ? C2C C3C C4C 121.471(1) . . ? C2C C3C H3C 119.3 . . ? C4C C3C H3C 119.3 . . ? C5C C4C C3C 117.548(1) . . ? C5C C4C C7C 119.242(2) . . ? C3C C4C C7C 123.208(1) . . ? C6C C5C C4C 122.130(1) . . ? C6C C5C H5C 118.9 . . ? C4C C5C H5C 118.9 . . ? C5C C6C C1C 118.331(2) . . ? C5C C6C H6C 120.8 . . ? C1C C6C H6C 120.8 . . ? C17C C7C C4C 126.430(2) . . ? C17C C7C H7C 116.8 . . ? C4C C7C H7C 116.8 . . ? C16C C11C C12C 121.447(1) . . ? C16C C11C Cl1G 114.869(2) . . ? C12C C11C Cl1G 123.682(2) . . ? C13C C12C C11C 119.055(1) . . ? C13C C12C H12C 120.5 . . ? C11C C12C H12C 120.5 . . ? C12C C13C C14C 121.472(1) . . ? C12C C13C H13C 119.3 . . ? C14C C13C H13C 119.3 . . ? C15C C14C C13C 117.564(2) . . ? C15C C14C C17C 119.212(2) . . ? C13C C14C C17C 123.2 . . ? C16C C15C C14C 122.126(1) . . ? C16C C15C H15C 118.9 . . ? C14C C15C H15C 118.9 . . ? C15C C16C C11C 118.333(2) . . ? C15C C16C H16C 120.8 . . ? C11C C16C H16C 120.8 . . ? C7C C17C C14C 126.413(1) . . ? C7C C17C H17C 116.8 . . ? C14C C17C H17C 116.8 . . ? O2D N1D O1D 122.161(2) . . ? O2H N1H O1H 122.140(2) . . ? O2H N1H C1D 121.676(2) . . ? O1H N1H C1D 116.163(1) . . ? N1H C1D C6D 123.317(2) . . ? N1H C1D C2D 115.221(2) . . ? C6D C1D C2D 121.452(1) . . ? C3D C2D C1D 119.065(1) . . ? C3D C2D H2D 120.5 . . ? C1D C2D H2D 120.5 . . ? C2D C3D C4D 121.471(1) . . ? C2D C3D H3D 119.3 . . ? C4D C3D H3D 119.3 . . ? C5D C4D C3D 117.548(1) . . ? C5D C4D C7D 119.242(2) . . ? C3D C4D C7D 123.208(1) . . ? C6D C5D C4D 122.130(1) . . ? C6D C5D H5D 118.9 . . ? C4D C5D H5D 118.9 . . ? C5D C6D C1D 118.331(1) . . ? C5D C6D H6D 120.8 . . ? C1D C6D H6D 120.8 . . ? C17D C7D C4D 126.430(2) . . ? C17D C7D H7D 116.8 . . ? C4D C7D H7D 116.8 . . ? C16D C11D C12D 121.447(2) . . ? C16D C11D Cl1H 114.869(2) . . ? C12D C11D Cl1H 123.682(2) . . ? C13D C12D C11D 119.055(1) . . ? C13D C12D H12D 120.5 . . ? C11D C12D H12D 120.5 . . ? C12D C13D C14D 121.472(1) . . ? C12D C13D H13D 119.3 . . ? C14D C13D H13D 119.3 . . ? C15D C14D C13D 117.564(1) . . ? C15D C14D C17D 119.212(1) . . ? C13D C14D C17D 123.222(1) . . ? C16D C15D C14D 122.126(1) . . ? C16D C15D H15D 118.9 . . ? C14D C15D H15D 118.9 . . ? C15D C16D C11D 118.333(1) . . ? C15D C16D H16D 120.8 . . ? C11D C16D H16D 120.8 . . ? C7D C17D C14D 126.413(1) . . ? C7D C17D H17D 116.8 . . ? C14D C17D H17D 116.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2E N1E C1A C6A -177.2 . . . . ? O1E N1E C1A C6A 1.2 . . . . ? O2E N1E C1A C2A 1.7 . . . . ? O1E N1E C1A C2A -180.0 . . . . ? N1E C1A C2A C3A -179.2 . . . . ? C6A C1A C2A C3A -0.3 . . . . ? C1A C2A C3A C4A 0.339(1) . . . . ? C2A C3A C4A C5A -0.5 . . . . ? C2A C3A C4A C7A 179.9 . . . . ? C3A C4A C5A C6A 0.6 . . . . ? C7A C4A C5A C6A -179.8 . . . . ? C4A C5A C6A C1A -0.5 . . . . ? N1E C1A C6A C5A 179.2 . . . . ? C2A C1A C6A C5A 0.4 . . . . ? C5A C4A C7A C17A 175.8 . . . . ? C3A C4A C7A C17A -4.7 . . . . ? C16A C11A C12A C13A 0.3 . . . . ? Cl1E C11A C12A C13A -179.3 . . . . ? C11A C12A C13A C14A -0.3 . . . . ? C12A C13A C14A C15A 0.5 . . . . ? C12A C13A C14A C17A -180.0 . . . . ? C13A C14A C15A C16A -0.6 . . . . ? C17A C14A C15A C16A 179.8 . . . . ? C14A C15A C16A C11A 0.5 . . . . ? C12A C11A C16A C15A -0.4 . . . . ? Cl1E C11A C16A C15A 179.2 . . . . ? C4A C7A C17A C14A 180.0 . . . . ? C15A C14A C17A C7A -175.8 . . . . ? C13A C14A C17A C7A 4.7 . . . . ? O2F N1F C1B C6B -177.2 . . . . ? O1F N1F C1B C6B 1.215(1) . . . . ? O2F N1F C1B C2B 1.7 . . . . ? O1F N1F C1B C2B -180.0 . . . . ? N1F C1B C2B C3B -179.2 . . . . ? C6B C1B C2B C3B -0.3 . . . . ? C1B C2B C3B C4B 0.3 . . . . ? C2B C3B C4B C5B -0.5 . . . . ? C2B C3B C4B C7B 179.9 . . . . ? C3B C4B C5B C6B 0.6 . . . . ? C7B C4B C5B C6B -179.8 . . . . ? C4B C5B C6B C1B -0.5 . . . . ? N1F C1B C6B C5B 179.2 . . . . ? C2B C1B C6B C5B 0.4 . . . . ? C5B C4B C7B C17B 175.8 . . . . ? C3B C4B C7B C17B -4.7 . . . . ? C16B C11B C12B C13B 0.276(1) . . . . ? Cl1F C11B C12B C13B -179.3 . . . . ? C11B C12B C13B C14B -0.327(1) . . . . ? C12B C13B C14B C15B 0.5 . . . . ? C12B C13B C14B C17B -180.0 . . . . ? C13B C14B C15B C16B -0.6 . . . . ? C17B C14B C15B C16B 179.8 . . . . ? C14B C15B C16B C11B 0.5 . . . . ? C12B C11B C16B C15B -0.4 . . . . ? Cl1F C11B C16B C15B 179.2 . . . . ? C4B C7B C17B C14B 180.0 . . . . ? C15B C14B C17B C7B -175.8 . . . . ? C13B C14B C17B C7B 4.7 . . . . ? O2G N1G C1C C6C -177.2 . . . . ? O1G N1G C1C C6C 1.2 . . . . ? O2G N1G C1C C2C 1.7 . . . . ? O1G N1G C1C C2C -180.0 . . . . ? N1G C1C C2C C3C -179.1 . . . . ? C6C C1C C2C C3C -0.275(2) . . . . ? C1C C2C C3C C4C 0.327(1) . . . . ? C2C C3C C4C C5C -0.5 . . . . ? C2C C3C C4C C7C 180.0 . . . . ? C3C C4C C5C C6C 0.6 . . . . ? C7C C4C C5C C6C -179.8 . . . . ? C4C C5C C6C C1C -0.5 . . . . ? N1G C1C C6C C5C 179.1 . . . . ? C2C C1C C6C C5C 0.370(1) . . . . ? C5C C4C C7C C17C 175.762(2) . . . . ? C3C C4C C7C C17C -4.7 . . . . ? C16C C11C C12C C13C 0.3 . . . . ? Cl1G C11C C12C C13C -179.263(1) . . . . ? C11C C12C C13C C14C -0.3 . . . . ? C12C C13C C14C C15C 0.4 . . . . ? C12C C13C C14C C17C -179.9 . . . . ? C13C C14C C15C C16C -0.6 . . . . ? C17C C14C C15C C16C 179.8 . . . . ? C14C C15C C16C C11C 0.540(1) . . . . ? C12C C11C C16C C15C -0.4 . . . . ? Cl1G C11C C16C C15C 179.2 . . . . ? C4C C7C C17C C14C -180.0 . . . . ? C15C C14C C17C C7C -175.8 . . . . ? C13C C14C C17C C7C 4.6 . . . . ? O2H N1H C1D C6D -177.2 . . . . ? O1H N1H C1D C6D 1.2 . . . . ? O2H N1H C1D C2D 1.7 . . . . ? O1H N1H C1D C2D -180.0 . . . . ? N1H C1D C2D C3D -179.1 . . . . ? C6D C1D C2D C3D -0.3 . . . . ? C1D C2D C3D C4D 0.3 . . . . ? C2D C3D C4D C5D -0.5 . . . . ? C2D C3D C4D C7D 180.0 . . . . ? C3D C4D C5D C6D 0.6 . . . . ? C7D C4D C5D C6D -179.8 . . . . ? C4D C5D C6D C1D -0.5 . . . . ? N1H C1D C6D C5D 179.1 . . . . ? C2D C1D C6D C5D 0.4 . . . . ? C5D C4D C7D C17D 175.762(1) . . . . ? C3D C4D C7D C17D -4.7 . . . . ? C16D C11D C12D C13D 0.3 . . . . ? Cl1H C11D C12D C13D -179.3 . . . . ? C11D C12D C13D C14D -0.3 . . . . ? C12D C13D C14D C15D 0.4 . . . . ? C12D C13D C14D C17D -179.9 . . . . ? C13D C14D C15D C16D -0.6 . . . . ? C17D C14D C15D C16D 179.8 . . . . ? C14D C15D C16D C11D 0.540(1) . . . . ? C12D C11D C16D C15D -0.389(2) . . . . ? Cl1H C11D C16D C15D 179.2 . . . . ? C4D C7D C17D C14D -180.0 . . . . ? C15D C14D C17D C7D -175.8 . . . . ? C13D C14D C17D C7D 4.6 . . . . ? _diffrn_measured_fraction_theta_max 0.709 _diffrn_reflns_theta_full 27.84 _diffrn_measured_fraction_theta_full 0.709 _refine_diff_density_max 0.112 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.043 # start Validation Reply Form _vrf_SYMMG01_CNS-DMSOII-big-A1 ; PROBLEM: Unrecognised _symmetry_space_group_name_H-M RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. ; _vrf_SYMMG02_CNS-DMSOII-big-A1 ; PROBLEM: Supplied _symmetry_space_group_name_H-M not recognised RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. ; _vrf_PLAT029_CNS-DMSOII-big-A1 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.71 RESPONSE: This A1 model was generated from its corresponding smaller unit cell P21 model, by doubling the b and c-axis. ; # end Validation Reply Form #===END data_CNS-EtOH-small-P21/c _database_code_depnum_ccdc_archive 'CCDC 761238' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall 'P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.91514(5) _cell_length_b 12.96036(16) _cell_length_c 12.22634(16) _cell_angle_alpha 90.00 _cell_angle_beta 93.1916(12) _cell_angle_gamma 90.00 _cell_volume 619.422(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5653 _cell_measurement_theta_min 4.7099 _cell_measurement_theta_max 31.8015 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.865659 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7100 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator synchrotron _diffrn_measurement_device_type 'Kuma 6-circle' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean 8.2896 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8011 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.59 _diffrn_reflns_theta_max 26.41 _reflns_number_total 2474 _reflns_number_gt 2006 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+0.0968P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2474 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1532 _refine_ls_wR_factor_gt 0.1487 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3708(6) -0.46093(9) -0.1758(2) 0.1139(8) Uani 0.50 1 d P . . N11 N 0.3617(12) -0.4169(3) -0.1720(4) 0.0806(9) Uani 0.50 1 d P . . O11 O 0.3170(12) -0.4973(3) -0.1234(3) 0.1299(14) Uani 0.50 1 d P . . O12 O 0.4996(7) -0.41139(19) -0.2586(2) 0.1142(8) Uani 0.50 1 d P . . C1 C 0.2613(3) -0.32937(11) -0.12295(11) 0.0753(4) Uani 1 1 d . . . C2 C 0.3157(3) -0.23937(12) -0.17922(10) 0.0801(4) Uani 1 1 d . . . H2A H 0.4138 -0.2410 -0.2467 0.096 Uiso 1 1 calc R . . C3 C 0.2230(3) -0.14731(11) -0.13416(11) 0.0762(4) Uani 1 1 d . . . H3A H 0.2576 -0.0863 -0.1720 0.091 Uiso 1 1 calc R . . C4 C 0.0779(3) -0.14357(9) -0.03277(10) 0.0667(3) Uani 1 1 d . . . C5 C 0.0278(3) -0.23627(10) 0.02088(10) 0.0729(4) Uani 1 1 d . . . H5A H -0.0703 -0.2352 0.0884 0.087 Uiso 1 1 calc R . . C6 C 0.1186(3) -0.32979(11) -0.02266(11) 0.0776(4) Uani 1 1 d . . . H6A H 0.0846 -0.3912 0.0146 0.093 Uiso 1 1 calc R . . C7 C -0.0244(3) -0.04665(9) 0.01847(11) 0.0721(4) Uani 1 1 d . . . H7 H -0.1349 -0.0522 0.0836 0.087 Uiso 1 1 calc R . . Cl11 Cl -0.3708(6) 0.46093(9) 0.1758(2) 0.1139(8) Uani 0.50 1 d P . . N1 N -0.3617(12) 0.4169(3) 0.1720(4) 0.0806(9) Uani 0.50 1 d P . . O1 O -0.3170(12) 0.4973(3) 0.1234(3) 0.1299(14) Uani 0.50 1 d P . . O2 O -0.4996(7) 0.41139(19) 0.2586(2) 0.1142(8) Uani 0.50 1 d P . . C11 C -0.2613(3) 0.32937(11) 0.12295(11) 0.0753(4) Uani 1 1 d . . . C12 C -0.3157(3) 0.23937(12) 0.17922(10) 0.0801(4) Uani 1 1 d . . . H12A H -0.4138 0.2410 0.2467 0.096 Uiso 1 1 calc R . . C13 C -0.2230(3) 0.14731(11) 0.13416(11) 0.0762(4) Uani 1 1 d . . . H13A H -0.2576 0.0863 0.1720 0.091 Uiso 1 1 calc R . . C14 C -0.0779(3) 0.14357(9) 0.03277(10) 0.0667(3) Uani 1 1 d . . . C15 C -0.0278(3) 0.23627(10) -0.02088(10) 0.0729(4) Uani 1 1 d . . . H15A H 0.0703 0.2352 -0.0884 0.087 Uiso 1 1 calc R . . C16 C -0.1186(3) 0.32979(11) 0.02266(11) 0.0776(4) Uani 1 1 d . . . H16A H -0.0846 0.3912 -0.0146 0.093 Uiso 1 1 calc R . . C17 C 0.0244(3) 0.04665(9) -0.01847(11) 0.0721(4) Uani 1 1 d . . . H17 H 0.1349 0.0522 -0.0836 0.087 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1140(8) 0.0938(15) 0.1337(13) -0.0460(14) 0.0047(8) 0.0242(11) N11 0.0779(17) 0.073(3) 0.091(2) -0.007(2) 0.0017(15) 0.008(2) O11 0.176(3) 0.0735(18) 0.144(3) 0.0048(17) 0.042(2) 0.0194(17) O12 0.153(2) 0.0902(15) 0.1027(16) -0.0252(13) 0.0322(15) 0.0191(14) C1 0.0611(7) 0.0883(9) 0.0761(8) -0.0156(7) 0.0001(6) 0.0055(6) C2 0.0699(8) 0.1055(11) 0.0657(8) -0.0039(7) 0.0104(6) -0.0019(7) C3 0.0723(8) 0.0840(9) 0.0731(8) 0.0065(6) 0.0099(6) -0.0034(6) C4 0.0545(6) 0.0777(8) 0.0679(7) -0.0021(6) 0.0019(5) -0.0019(5) C5 0.0708(7) 0.0823(8) 0.0663(7) 0.0001(6) 0.0099(6) 0.0007(6) C6 0.0747(8) 0.0787(8) 0.0794(8) 0.0036(6) 0.0051(6) 0.0018(6) C7 0.0632(7) 0.0827(8) 0.0710(7) 0.0029(6) 0.0080(5) -0.0026(6) Cl11 0.1140(8) 0.0938(15) 0.1337(13) -0.0460(14) 0.0047(8) 0.0242(11) N1 0.0779(17) 0.073(3) 0.091(2) -0.007(2) 0.0017(15) 0.008(2) O1 0.176(3) 0.0735(18) 0.144(3) 0.0048(17) 0.042(2) 0.0194(17) O2 0.153(2) 0.0902(15) 0.1027(16) -0.0252(13) 0.0322(15) 0.0191(14) C11 0.0611(7) 0.0883(9) 0.0761(8) -0.0156(7) 0.0001(6) 0.0055(6) C12 0.0699(8) 0.1055(11) 0.0657(8) -0.0039(7) 0.0104(6) -0.0019(7) C13 0.0723(8) 0.0840(9) 0.0731(8) 0.0065(6) 0.0099(6) -0.0034(6) C14 0.0545(6) 0.0777(8) 0.0679(7) -0.0021(6) 0.0019(5) -0.0019(5) C15 0.0708(7) 0.0823(8) 0.0663(7) 0.0001(6) 0.0099(6) 0.0007(6) C16 0.0747(8) 0.0787(8) 0.0794(8) 0.0036(6) 0.0051(6) 0.0018(6) C17 0.0632(7) 0.0827(8) 0.0710(7) 0.0029(6) 0.0080(5) -0.0026(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.574(4) . ? Cl1 O11 0.831(3) . ? Cl1 O12 1.322(3) . ? Cl1 C1 1.8813(18) . ? N11 O12 1.217(6) . ? N11 O11 1.217(7) . ? N11 C1 1.352(4) . ? C1 C6 1.3754(19) . ? C1 C2 1.377(2) . ? C2 C3 1.372(2) . ? C2 H2A 0.9300 . ? C3 C4 1.3929(18) . ? C3 H3A 0.9300 . ? C4 C5 1.3879(17) . ? C4 C7 1.4692(18) . ? C5 C6 1.3785(18) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.309(2) . ? C7 H7 0.9300 . ? Cl11 N1 0.574(4) . ? Cl11 O1 0.831(3) . ? Cl11 O2 1.322(3) . ? Cl11 C11 1.8813(18) . ? N1 O2 1.217(6) . ? N1 O1 1.217(7) . ? N1 C11 1.352(4) . ? C11 C16 1.3754(19) . ? C11 C12 1.377(2) . ? C12 C13 1.372(2) . ? C12 H12A 0.9300 . ? C13 C14 1.3929(18) . ? C13 H13A 0.9300 . ? C14 C15 1.3879(17) . ? C14 C17 1.4692(18) . ? C15 C16 1.3785(18) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 118.8(10) . . ? N11 Cl1 O12 66.8(7) . . ? O11 Cl1 O12 171.3(4) . . ? N11 Cl1 C1 19.0(7) . . ? O11 Cl1 C1 100.2(4) . . ? O12 Cl1 C1 85.80(13) . . ? Cl1 N11 O12 87.5(7) . . ? Cl1 N11 O11 36.8(7) . . ? O12 N11 O11 123.9(4) . . ? Cl1 N11 C1 153.0(10) . . ? O12 N11 C1 119.4(4) . . ? O11 N11 C1 116.6(4) . . ? Cl1 O11 N11 24.4(3) . . ? N11 O12 Cl1 25.69(17) . . ? N11 C1 C6 122.3(3) . . ? N11 C1 C2 115.6(3) . . ? C6 C1 C2 122.05(13) . . ? N11 C1 Cl1 8.0(3) . . ? C6 C1 Cl1 114.47(14) . . ? C2 C1 Cl1 123.48(13) . . ? C3 C2 C1 118.98(12) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 121.19(13) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C5 C4 C3 117.77(12) . . ? C5 C4 C7 119.30(11) . . ? C3 C4 C7 122.93(12) . . ? C6 C5 C4 122.16(12) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C5 C6 C1 117.85(13) . . ? C5 C6 H6A 121.1 . . ? C1 C6 H6A 121.1 . . ? C17 C7 C4 126.46(16) . . ? C17 C7 H7 116.8 . . ? C4 C7 H7 116.8 . . ? N1 Cl11 O1 118.8(10) . . ? N1 Cl11 O2 66.8(7) . . ? O1 Cl11 O2 171.3(4) . . ? N1 Cl11 C11 19.0(7) . . ? O1 Cl11 C11 100.2(4) . . ? O2 Cl11 C11 85.80(13) . . ? Cl11 N1 O2 87.5(7) . . ? Cl11 N1 O1 36.8(7) . . ? O2 N1 O1 123.9(4) . . ? Cl11 N1 C11 153.0(10) . . ? O2 N1 C11 119.4(4) . . ? O1 N1 C11 116.6(4) . . ? Cl11 O1 N1 24.4(3) . . ? N1 O2 Cl11 25.69(17) . . ? N1 C11 C16 122.3(3) . . ? N1 C11 C12 115.6(3) . . ? C16 C11 C12 122.05(13) . . ? N1 C11 Cl11 8.0(3) . . ? C16 C11 Cl11 114.47(14) . . ? C12 C11 Cl11 123.48(13) . . ? C13 C12 C11 118.98(12) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C14 121.19(13) . . ? C12 C13 H13A 119.4 . . ? C14 C13 H13A 119.4 . . ? C15 C14 C13 117.77(12) . . ? C15 C14 C17 119.30(11) . . ? C13 C14 C17 122.93(12) . . ? C16 C15 C14 122.16(12) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C15 C16 C11 117.85(13) . . ? C15 C16 H16A 121.1 . . ? C11 C16 H16A 121.1 . . ? C7 C17 C14 126.46(16) . . ? C7 C17 H17 116.8 . . ? C14 C17 H17 116.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 172.7(5) . . . . ? C1 Cl1 N11 O12 -175(2) . . . . ? O12 Cl1 N11 O11 -172.7(5) . . . . ? C1 Cl1 N11 O11 12(2) . . . . ? O11 Cl1 N11 C1 -12(2) . . . . ? O12 Cl1 N11 C1 175(2) . . . . ? O12 Cl1 O11 N11 129(3) . . . . ? C1 Cl1 O11 N11 -4.1(8) . . . . ? O12 N11 O11 Cl1 -8.8(7) . . . . ? C1 N11 O11 Cl1 173.7(11) . . . . ? O11 N11 O12 Cl1 5.3(4) . . . . ? C1 N11 O12 Cl1 -177.4(10) . . . . ? O11 Cl1 O12 N11 -132(3) . . . . ? C1 Cl1 O12 N11 1.7(6) . . . . ? Cl1 N11 C1 C6 9(2) . . . . ? O12 N11 C1 C6 -176.9(3) . . . . ? O11 N11 C1 C6 0.7(6) . . . . ? Cl1 N11 C1 C2 -172.0(18) . . . . ? O12 N11 C1 C2 2.2(5) . . . . ? O11 N11 C1 C2 179.7(4) . . . . ? O12 N11 C1 Cl1 174(2) . . . . ? O11 N11 C1 Cl1 -8.3(15) . . . . ? O11 Cl1 C1 N11 169(2) . . . . ? O12 Cl1 C1 N11 -4.7(18) . . . . ? N11 Cl1 C1 C6 -171.7(19) . . . . ? O11 Cl1 C1 C6 -2.8(4) . . . . ? O12 Cl1 C1 C6 -176.40(17) . . . . ? N11 Cl1 C1 C2 8.7(19) . . . . ? O11 Cl1 C1 C2 177.6(4) . . . . ? O12 Cl1 C1 C2 4.0(2) . . . . ? N11 C1 C2 C3 -179.5(2) . . . . ? C6 C1 C2 C3 -0.4(2) . . . . ? Cl1 C1 C2 C3 179.20(12) . . . . ? C1 C2 C3 C4 0.4(2) . . . . ? C2 C3 C4 C5 -0.48(19) . . . . ? C2 C3 C4 C7 179.89(11) . . . . ? C3 C4 C5 C6 0.46(19) . . . . ? C7 C4 C5 C6 -179.89(11) . . . . ? C4 C5 C6 C1 -0.4(2) . . . . ? N11 C1 C6 C5 179.4(3) . . . . ? C2 C1 C6 C5 0.3(2) . . . . ? Cl1 C1 C6 C5 -179.26(12) . . . . ? C5 C4 C7 C17 175.65(16) . . . . ? C3 C4 C7 C17 -4.7(2) . . . . ? O1 Cl11 N1 O2 -172.7(5) . . . . ? C11 Cl11 N1 O2 175(2) . . . . ? O2 Cl11 N1 O1 172.7(5) . . . . ? C11 Cl11 N1 O1 -12(2) . . . . ? O1 Cl11 N1 C11 12(2) . . . . ? O2 Cl11 N1 C11 -175(2) . . . . ? O2 Cl11 O1 N1 -129(3) . . . . ? C11 Cl11 O1 N1 4.1(8) . . . . ? O2 N1 O1 Cl11 8.8(7) . . . . ? C11 N1 O1 Cl11 -173.7(11) . . . . ? O1 N1 O2 Cl11 -5.3(4) . . . . ? C11 N1 O2 Cl11 177.4(10) . . . . ? O1 Cl11 O2 N1 132(3) . . . . ? C11 Cl11 O2 N1 -1.7(6) . . . . ? Cl11 N1 C11 C16 -9(2) . . . . ? O2 N1 C11 C16 176.9(3) . . . . ? O1 N1 C11 C16 -0.7(6) . . . . ? Cl11 N1 C11 C12 172.0(18) . . . . ? O2 N1 C11 C12 -2.2(5) . . . . ? O1 N1 C11 C12 -179.7(4) . . . . ? O2 N1 C11 Cl11 -174(2) . . . . ? O1 N1 C11 Cl11 8.3(15) . . . . ? O1 Cl11 C11 N1 -169(2) . . . . ? O2 Cl11 C11 N1 4.7(18) . . . . ? N1 Cl11 C11 C16 171.7(19) . . . . ? O1 Cl11 C11 C16 2.8(4) . . . . ? O2 Cl11 C11 C16 176.40(17) . . . . ? N1 Cl11 C11 C12 -8.7(19) . . . . ? O1 Cl11 C11 C12 -177.6(4) . . . . ? O2 Cl11 C11 C12 -4.0(2) . . . . ? N1 C11 C12 C13 179.5(2) . . . . ? C16 C11 C12 C13 0.4(2) . . . . ? Cl11 C11 C12 C13 -179.20(12) . . . . ? C11 C12 C13 C14 -0.4(2) . . . . ? C12 C13 C14 C15 0.48(19) . . . . ? C12 C13 C14 C17 -179.89(11) . . . . ? C13 C14 C15 C16 -0.46(19) . . . . ? C17 C14 C15 C16 179.89(11) . . . . ? C14 C15 C16 C11 0.4(2) . . . . ? N1 C11 C16 C15 -179.4(3) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? Cl11 C11 C16 C15 179.26(12) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.65(16) . . . . ? C13 C14 C17 C7 4.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.114 _refine_diff_density_min -0.109 _refine_diff_density_rms 0.021 # start Validation Reply Form _vrf_SYMMG02_CNS-EtOH-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; # end Validation Reply Form #===END data_CNS-EtOH-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761239' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.91514(5) _cell_length_b 12.96036(16) _cell_length_c 12.22634(16) _cell_angle_alpha 90.00 _cell_angle_beta 93.1916(12) _cell_angle_gamma 90.00 _cell_volume 619.422(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5653 _cell_measurement_theta_min 4.7099 _cell_measurement_theta_max 31.8015 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.865659 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7100 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator synchrotron _diffrn_measurement_device_type 'Kuma 6-circle' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean 8.2896 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8011 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.59 _diffrn_reflns_theta_max 26.41 _reflns_number_total 2474 _reflns_number_gt 2006 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+0.0968P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.44(19) _refine_ls_number_reflns 2474 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.948 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3711(5) -0.46062(8) -0.17616(17) 0.1141(6) Uani 0.4326(15) 1 d P . . N11 N 0.3617(10) -0.4166(3) -0.1715(3) 0.0826(8) Uani 0.5674(15) 1 d P . . O11 O 0.3169(9) -0.4971(2) -0.1239(3) 0.1280(11) Uani 0.5674(15) 1 d P . . O12 O 0.4997(6) -0.41204(16) -0.25861(17) 0.1129(7) Uani 0.5674(15) 1 d P . . C1 C 0.2615(3) -0.32942(9) -0.12301(10) 0.0753(3) Uani 1 1 d . . . C2 C 0.3157(3) -0.23911(11) -0.17937(9) 0.0801(3) Uani 1 1 d . . . H2A H 0.4138 -0.2405 -0.2469 0.096 Uiso 1 1 calc R . . C3 C 0.2227(3) -0.14746(9) -0.13415(9) 0.0767(3) Uani 1 1 d . . . H3A H 0.2571 -0.0864 -0.1720 0.092 Uiso 1 1 calc R . . C4 C 0.0779(2) -0.14348(8) -0.03286(8) 0.0666(3) Uani 1 1 d . . . C5 C 0.0277(3) -0.23617(9) 0.02095(9) 0.0730(3) Uani 1 1 d . . . H5A H -0.0706 -0.2352 0.0885 0.088 Uiso 1 1 calc R . . C6 C 0.1188(3) -0.32945(9) -0.02255(10) 0.0771(3) Uani 1 1 d . . . H6A H 0.0849 -0.3908 0.0148 0.092 Uiso 1 1 calc R . . C7 C -0.0245(3) -0.04673(8) 0.01859(9) 0.0715(3) Uani 1 1 d . . . H7 H -0.1345 -0.0523 0.0838 0.086 Uiso 1 1 calc R . . Cl11 Cl -0.3711(5) 0.46062(8) 0.17616(17) 0.1141(6) Uani 0.5674(15) 1 d P . . N1 N -0.3617(10) 0.4166(3) 0.1715(3) 0.0826(8) Uani 0.4326(15) 1 d P . . O1 O -0.3169(9) 0.4971(2) 0.1239(3) 0.1280(11) Uani 0.4326(15) 1 d P . . O2 O -0.4997(6) 0.41204(16) 0.25861(17) 0.1129(7) Uani 0.4326(15) 1 d P . . C11 C -0.2615(3) 0.32942(9) 0.12301(10) 0.0753(3) Uani 1 1 d . . . C12 C -0.3157(3) 0.23911(11) 0.17937(9) 0.0801(3) Uani 1 1 d . . . H12A H -0.4138 0.2405 0.2469 0.096 Uiso 1 1 calc R . . C13 C -0.2227(3) 0.14746(9) 0.13415(9) 0.0767(3) Uani 1 1 d . . . H13A H -0.2571 0.0864 0.1720 0.092 Uiso 1 1 calc R . . C14 C -0.0779(2) 0.14348(8) 0.03286(8) 0.0666(3) Uani 1 1 d . . . C15 C -0.0277(3) 0.23617(9) -0.02095(9) 0.0730(3) Uani 1 1 d . . . H15A H 0.0706 0.2352 -0.0885 0.088 Uiso 1 1 calc R . . C16 C -0.1188(3) 0.32945(9) 0.02255(10) 0.0771(3) Uani 1 1 d . . . H16A H -0.0849 0.3908 -0.0148 0.092 Uiso 1 1 calc R . . C17 C 0.0245(3) 0.04673(8) -0.01859(9) 0.0715(3) Uani 1 1 d . . . H17 H 0.1345 0.0523 -0.0838 0.086 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1131(7) 0.0956(12) 0.1333(11) -0.0470(11) 0.0044(7) 0.0239(9) N11 0.0789(15) 0.076(2) 0.093(2) -0.0074(18) -0.0001(13) 0.0077(17) O11 0.170(2) 0.0756(15) 0.142(2) 0.0059(14) 0.0418(18) 0.0185(14) O12 0.1532(19) 0.0898(13) 0.0987(13) -0.0229(11) 0.0352(13) 0.0188(12) C1 0.0607(6) 0.0885(8) 0.0762(7) -0.0146(6) 0.0003(5) 0.0055(5) C2 0.0695(7) 0.1057(9) 0.0658(6) -0.0035(6) 0.0107(5) -0.0014(6) C3 0.0717(6) 0.0851(7) 0.0740(7) 0.0072(5) 0.0091(5) -0.0040(5) C4 0.0543(5) 0.0782(7) 0.0673(6) -0.0024(5) 0.0020(4) -0.0017(4) C5 0.0703(6) 0.0830(7) 0.0664(6) 0.0012(5) 0.0103(5) 0.0003(5) C6 0.0749(7) 0.0775(7) 0.0790(7) 0.0027(5) 0.0055(5) 0.0012(5) C7 0.0631(6) 0.0816(7) 0.0702(6) 0.0026(5) 0.0076(5) -0.0024(5) Cl11 0.1131(7) 0.0956(12) 0.1333(11) -0.0470(11) 0.0044(7) 0.0239(9) N1 0.0789(15) 0.076(2) 0.093(2) -0.0074(18) -0.0001(13) 0.0077(17) O1 0.170(2) 0.0756(15) 0.142(2) 0.0059(14) 0.0418(18) 0.0185(14) O2 0.1532(19) 0.0898(13) 0.0987(13) -0.0229(11) 0.0352(13) 0.0188(12) C11 0.0607(6) 0.0885(8) 0.0762(7) -0.0146(6) 0.0003(5) 0.0055(5) C12 0.0695(7) 0.1057(9) 0.0658(6) -0.0035(6) 0.0107(5) -0.0014(6) C13 0.0717(6) 0.0851(7) 0.0740(7) 0.0072(5) 0.0091(5) -0.0040(5) C14 0.0543(5) 0.0782(7) 0.0673(6) -0.0024(5) 0.0020(4) -0.0017(4) C15 0.0703(6) 0.0830(7) 0.0664(6) 0.0012(5) 0.0103(5) 0.0003(5) C16 0.0749(7) 0.0775(7) 0.0790(7) 0.0027(5) 0.0055(5) 0.0012(5) C17 0.0631(6) 0.0816(7) 0.0702(6) 0.0026(5) 0.0076(5) -0.0024(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.574(3) . ? Cl1 O11 0.832(3) . ? Cl1 O12 1.313(3) . ? Cl1 C1 1.8786(15) . ? N11 O11 1.212(6) . ? N11 O12 1.222(5) . ? N11 C1 1.345(3) . ? C1 C6 1.3775(16) . ? C1 C2 1.3806(17) . ? C2 C3 1.3680(17) . ? C2 H2A 0.9300 . ? C3 C4 1.3913(16) . ? C3 H3A 0.9300 . ? C4 C5 1.3890(15) . ? C4 C7 1.4685(15) . ? C5 C6 1.3757(15) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.312(2) . ? C7 H7 0.9300 . ? Cl11 N1 0.574(3) . ? Cl11 O1 0.832(3) . ? Cl11 O2 1.313(3) . ? Cl11 C11 1.8786(15) . ? N1 O1 1.212(6) . ? N1 O2 1.222(5) . ? N1 C11 1.345(3) . ? C11 C16 1.3775(16) . ? C11 C12 1.3806(17) . ? C12 C13 1.3680(17) . ? C12 H12A 0.9300 . ? C13 C14 1.3913(16) . ? C13 H13A 0.9300 . ? C14 C15 1.3890(15) . ? C14 C17 1.4685(15) . ? C15 C16 1.3757(15) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 117.9(8) . . ? N11 Cl1 O12 68.2(6) . . ? O11 Cl1 O12 171.1(3) . . ? N11 Cl1 C1 18.2(6) . . ? O11 Cl1 C1 100.1(3) . . ? O12 Cl1 C1 86.34(11) . . ? Cl1 N11 O11 37.4(6) . . ? Cl1 N11 O12 85.9(6) . . ? O11 N11 O12 123.0(3) . . ? Cl1 N11 C1 154.1(8) . . ? O11 N11 C1 117.2(3) . . ? O12 N11 C1 119.8(3) . . ? Cl1 O11 N11 24.8(3) . . ? N11 O12 Cl1 25.87(15) . . ? N11 C1 C6 122.4(2) . . ? N11 C1 C2 115.8(2) . . ? C6 C1 C2 121.77(11) . . ? N11 C1 Cl1 7.7(2) . . ? C6 C1 Cl1 114.83(12) . . ? C2 C1 Cl1 123.39(11) . . ? C3 C2 C1 118.85(10) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C2 C3 C4 121.52(11) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C5 C4 C3 117.70(10) . . ? C5 C4 C7 119.10(10) . . ? C3 C4 C7 123.19(10) . . ? C6 C5 C4 122.03(10) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C5 C6 C1 118.12(11) . . ? C5 C6 H6A 120.9 . . ? C1 C6 H6A 120.9 . . ? C17 C7 C4 126.26(13) . . ? C17 C7 H7 116.9 . . ? C4 C7 H7 116.9 . . ? N1 Cl11 O1 117.9(8) . . ? N1 Cl11 O2 68.2(6) . . ? O1 Cl11 O2 171.1(3) . . ? N1 Cl11 C11 18.2(6) . . ? O1 Cl11 C11 100.1(3) . . ? O2 Cl11 C11 86.34(11) . . ? Cl11 N1 O1 37.4(6) . . ? Cl11 N1 O2 85.9(6) . . ? O1 N1 O2 123.0(3) . . ? Cl11 N1 C11 154.1(8) . . ? O1 N1 C11 117.2(3) . . ? O2 N1 C11 119.8(3) . . ? Cl11 O1 N1 24.8(3) . . ? N1 O2 Cl11 25.87(15) . . ? N1 C11 C16 122.4(2) . . ? N1 C11 C12 115.8(2) . . ? C16 C11 C12 121.77(11) . . ? N1 C11 Cl11 7.7(2) . . ? C16 C11 Cl11 114.83(12) . . ? C12 C11 Cl11 123.39(11) . . ? C13 C12 C11 118.85(10) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? C12 C13 C14 121.52(11) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C15 C14 C13 117.70(10) . . ? C15 C14 C17 119.10(10) . . ? C13 C14 C17 123.19(10) . . ? C16 C15 C14 122.03(10) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C15 C16 C11 118.12(11) . . ? C15 C16 H16A 120.9 . . ? C11 C16 H16A 120.9 . . ? C7 C17 C14 126.26(13) . . ? C7 C17 H17 116.9 . . ? C14 C17 H17 116.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 Cl1 N11 O11 -172.8(4) . . . . ? C1 Cl1 N11 O11 13.5(19) . . . . ? O11 Cl1 N11 O12 172.8(4) . . . . ? C1 Cl1 N11 O12 -173.7(17) . . . . ? O11 Cl1 N11 C1 -13.5(19) . . . . ? O12 Cl1 N11 C1 173.7(17) . . . . ? O12 Cl1 O11 N11 131(3) . . . . ? C1 Cl1 O11 N11 -4.3(6) . . . . ? O12 N11 O11 Cl1 -8.6(5) . . . . ? C1 N11 O11 Cl1 173.4(10) . . . . ? O11 N11 O12 Cl1 5.2(3) . . . . ? C1 N11 O12 Cl1 -176.8(8) . . . . ? O11 Cl1 O12 N11 -134(3) . . . . ? C1 Cl1 O12 N11 2.0(5) . . . . ? Cl1 N11 C1 C6 10.2(17) . . . . ? O11 N11 C1 C6 1.1(5) . . . . ? O12 N11 C1 C6 -177.0(2) . . . . ? Cl1 N11 C1 C2 -170.8(16) . . . . ? O11 N11 C1 C2 -180.0(3) . . . . ? O12 N11 C1 C2 2.0(4) . . . . ? O11 N11 C1 Cl1 -9.2(13) . . . . ? O12 N11 C1 Cl1 172.7(19) . . . . ? O11 Cl1 C1 N11 167.9(18) . . . . ? O12 Cl1 C1 N11 -5.9(16) . . . . ? N11 Cl1 C1 C6 -170.5(16) . . . . ? O11 Cl1 C1 C6 -2.6(3) . . . . ? O12 Cl1 C1 C6 -176.35(14) . . . . ? N11 Cl1 C1 C2 10.0(17) . . . . ? O11 Cl1 C1 C2 177.8(3) . . . . ? O12 Cl1 C1 C2 4.09(18) . . . . ? N11 C1 C2 C3 -179.4(2) . . . . ? C6 C1 C2 C3 -0.40(17) . . . . ? Cl1 C1 C2 C3 179.14(11) . . . . ? C1 C2 C3 C4 0.46(17) . . . . ? C2 C3 C4 C5 -0.52(16) . . . . ? C2 C3 C4 C7 179.82(10) . . . . ? C3 C4 C5 C6 0.53(16) . . . . ? C7 C4 C5 C6 -179.80(10) . . . . ? C4 C5 C6 C1 -0.48(17) . . . . ? N11 C1 C6 C5 179.3(2) . . . . ? C2 C1 C6 C5 0.41(17) . . . . ? Cl1 C1 C6 C5 -179.17(10) . . . . ? C5 C4 C7 C17 175.71(13) . . . . ? C3 C4 C7 C17 -4.6(2) . . . . ? O2 Cl11 N1 O1 172.8(4) . . . . ? C11 Cl11 N1 O1 -13.5(19) . . . . ? O1 Cl11 N1 O2 -172.8(4) . . . . ? C11 Cl11 N1 O2 173.7(17) . . . . ? O1 Cl11 N1 C11 13.5(19) . . . . ? O2 Cl11 N1 C11 -173.7(17) . . . . ? O2 Cl11 O1 N1 -131(3) . . . . ? C11 Cl11 O1 N1 4.3(6) . . . . ? O2 N1 O1 Cl11 8.6(5) . . . . ? C11 N1 O1 Cl11 -173.4(10) . . . . ? O1 N1 O2 Cl11 -5.2(3) . . . . ? C11 N1 O2 Cl11 176.8(8) . . . . ? O1 Cl11 O2 N1 134(3) . . . . ? C11 Cl11 O2 N1 -2.0(5) . . . . ? Cl11 N1 C11 C16 -10.2(17) . . . . ? O1 N1 C11 C16 -1.1(5) . . . . ? O2 N1 C11 C16 177.0(2) . . . . ? Cl11 N1 C11 C12 170.8(16) . . . . ? O1 N1 C11 C12 180.0(3) . . . . ? O2 N1 C11 C12 -2.0(4) . . . . ? O1 N1 C11 Cl11 9.2(13) . . . . ? O2 N1 C11 Cl11 -172.7(19) . . . . ? O1 Cl11 C11 N1 -167.9(18) . . . . ? O2 Cl11 C11 N1 5.9(16) . . . . ? N1 Cl11 C11 C16 170.5(16) . . . . ? O1 Cl11 C11 C16 2.6(3) . . . . ? O2 Cl11 C11 C16 176.35(14) . . . . ? N1 Cl11 C11 C12 -10.0(17) . . . . ? O1 Cl11 C11 C12 -177.8(3) . . . . ? O2 Cl11 C11 C12 -4.09(18) . . . . ? N1 C11 C12 C13 179.4(2) . . . . ? C16 C11 C12 C13 0.40(17) . . . . ? Cl11 C11 C12 C13 -179.14(11) . . . . ? C11 C12 C13 C14 -0.46(17) . . . . ? C12 C13 C14 C15 0.52(16) . . . . ? C12 C13 C14 C17 -179.82(10) . . . . ? C13 C14 C15 C16 -0.53(16) . . . . ? C17 C14 C15 C16 179.80(10) . . . . ? C14 C15 C16 C11 0.48(17) . . . . ? N1 C11 C16 C15 -179.3(2) . . . . ? C12 C11 C16 C15 -0.41(17) . . . . ? Cl11 C11 C16 C15 179.17(10) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.71(13) . . . . ? C13 C14 C17 C7 4.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.117 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.022 # start Validation Reply Form _vrf_SYMMG02_CNS-EtOH-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; # end Validation Reply Form #===END data_CNS-MeOH-small-P21/c _database_code_depnum_ccdc_archive 'CCDC 761240' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall 'P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9239(3) _cell_length_b 12.9707(9) _cell_length_c 12.2375(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.236(3) _cell_angle_gamma 90.00 _cell_volume 621.84(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3493 _cell_measurement_theta_min 3.141 _cell_measurement_theta_max 22.9775 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.497814 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3481 _diffrn_reflns_av_R_equivalents 0.0100 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.79 _reflns_number_total 2510 _reflns_number_gt 1326 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0222P)^2^+0.2256P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2510 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1213 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1367 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.152 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3690(14) -0.46069(16) -0.1749(5) 0.116(2) Uani 0.50 1 d P . . N11 N 0.364(3) -0.4168(6) -0.1742(12) 0.082(2) Uani 0.50 1 d P . . O11 O 0.316(2) -0.4969(6) -0.1225(5) 0.131(3) Uani 0.50 1 d P . . O12 O 0.4993(11) -0.4123(3) -0.2582(3) 0.1156(13) Uani 0.50 1 d P . . C1 C 0.2611(5) -0.32911(17) -0.12314(19) 0.0733(6) Uani 1 1 d . . . C2 C 0.3154(5) -0.2392(2) -0.17905(18) 0.0827(7) Uani 1 1 d . . . H2A H 0.4140 -0.2407 -0.2464 0.099 Uiso 1 1 calc R . . C3 C 0.2225(5) -0.14755(17) -0.13442(17) 0.0761(6) Uani 1 1 d . . . H3A H 0.2559 -0.0867 -0.1725 0.091 Uiso 1 1 calc R . . C4 C 0.0783(5) -0.14338(16) -0.03251(17) 0.0672(6) Uani 1 1 d . . . C5 C 0.0287(5) -0.23560(16) 0.02063(17) 0.0738(6) Uani 1 1 d . . . H5A H -0.0689 -0.2346 0.0881 0.089 Uiso 1 1 calc R . . C6 C 0.1189(5) -0.32943(17) -0.02287(19) 0.0785(6) Uani 1 1 d . . . H6A H 0.0847 -0.3907 0.0144 0.094 Uiso 1 1 calc R . . C7 C -0.0237(5) -0.04636(14) 0.01829(18) 0.0742(6) Uani 1 1 d . . . H7A H -0.1337 -0.0518 0.0834 0.089 Uiso 1 1 calc R . . Cl11 Cl -0.3690(14) 0.46069(16) 0.1749(5) 0.116(2) Uani 0.50 1 d P . . N1 N -0.364(3) 0.4168(6) 0.1742(12) 0.082(2) Uani 0.50 1 d P . . O1 O -0.316(2) 0.4969(6) 0.1225(5) 0.131(3) Uani 0.50 1 d P . . O2 O -0.4993(11) 0.4123(3) 0.2582(3) 0.1156(13) Uani 0.50 1 d P . . C11 C -0.2611(5) 0.32911(17) 0.12314(19) 0.0733(6) Uani 1 1 d . . . C12 C -0.3154(5) 0.2392(2) 0.17905(18) 0.0827(7) Uani 1 1 d . . . H12A H -0.4140 0.2407 0.2464 0.099 Uiso 1 1 calc R . . C13 C -0.2225(5) 0.14755(17) 0.13442(17) 0.0761(6) Uani 1 1 d . . . H13A H -0.2559 0.0867 0.1725 0.091 Uiso 1 1 calc R . . C14 C -0.0783(5) 0.14338(16) 0.03251(17) 0.0672(6) Uani 1 1 d . . . C15 C -0.0287(5) 0.23560(16) -0.02063(17) 0.0738(6) Uani 1 1 d . . . H15A H 0.0689 0.2346 -0.0881 0.089 Uiso 1 1 calc R . . C16 C -0.1189(5) 0.32943(17) 0.02287(19) 0.0785(6) Uani 1 1 d . . . H16A H -0.0847 0.3907 -0.0144 0.094 Uiso 1 1 calc R . . C17 C 0.0237(5) 0.04636(14) -0.01829(18) 0.0742(6) Uani 1 1 d . . . H17A H 0.1337 0.0518 -0.0834 0.089 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1194(18) 0.094(4) 0.133(3) -0.044(4) 0.006(2) 0.025(3) N11 0.076(4) 0.066(6) 0.104(7) 0.007(6) -0.001(4) 0.004(5) O11 0.175(5) 0.078(4) 0.141(6) 0.006(3) 0.034(4) 0.016(3) O12 0.154(4) 0.095(3) 0.101(3) -0.030(2) 0.032(3) 0.016(2) C1 0.0622(13) 0.0795(16) 0.0778(16) -0.0148(13) -0.0012(11) 0.0059(12) C2 0.0709(14) 0.1101(19) 0.0679(15) -0.0042(14) 0.0104(12) -0.0007(13) C3 0.0705(14) 0.0845(15) 0.0741(15) 0.0073(12) 0.0099(11) -0.0017(12) C4 0.0530(11) 0.0792(14) 0.0692(14) -0.0046(12) 0.0020(10) 0.0006(10) C5 0.0713(14) 0.0848(15) 0.0660(14) 0.0021(12) 0.0092(11) -0.0023(12) C6 0.0755(14) 0.0766(15) 0.0834(17) 0.0030(12) 0.0043(12) 0.0031(12) C7 0.0637(12) 0.0845(15) 0.0746(14) 0.0054(12) 0.0051(10) -0.0030(12) Cl11 0.1194(18) 0.094(4) 0.133(3) -0.044(4) 0.006(2) 0.025(3) N1 0.076(4) 0.066(6) 0.104(7) 0.007(6) -0.001(4) 0.004(5) O1 0.175(5) 0.078(4) 0.141(6) 0.006(3) 0.034(4) 0.016(3) O2 0.154(4) 0.095(3) 0.101(3) -0.030(2) 0.032(3) 0.016(2) C11 0.0622(13) 0.0795(16) 0.0778(16) -0.0148(13) -0.0012(11) 0.0059(12) C12 0.0709(14) 0.1101(19) 0.0679(15) -0.0042(14) 0.0104(12) -0.0007(13) C13 0.0705(14) 0.0845(15) 0.0741(15) 0.0073(12) 0.0099(11) -0.0017(12) C14 0.0530(11) 0.0792(14) 0.0692(14) -0.0046(12) 0.0020(10) 0.0006(10) C15 0.0713(14) 0.0848(15) 0.0660(14) 0.0021(12) 0.0092(11) -0.0023(12) C16 0.0755(14) 0.0766(15) 0.0834(17) 0.0030(12) 0.0043(12) 0.0031(12) C17 0.0637(12) 0.0845(15) 0.0746(14) 0.0054(12) 0.0051(10) -0.0030(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.570(8) . ? Cl1 O11 0.831(6) . ? Cl1 O12 1.323(7) . ? Cl1 C1 1.877(3) . ? N11 O12 1.185(15) . ? N11 O11 1.236(17) . ? N11 C1 1.369(8) . ? C1 C2 1.375(3) . ? C1 C6 1.376(3) . ? C2 C3 1.366(3) . ? C2 H2A 0.9300 . ? C3 C4 1.399(3) . ? C3 H3A 0.9300 . ? C4 C5 1.380(3) . ? C4 C7 1.469(3) . ? C5 C6 1.382(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.300(3) . ? C7 H7A 0.9300 . ? Cl11 N1 0.570(8) . ? Cl11 O1 0.831(6) . ? Cl11 O2 1.323(7) . ? Cl11 C11 1.877(3) . ? N1 O2 1.185(15) . ? N1 O1 1.236(17) . ? N1 C11 1.369(8) . ? C11 C12 1.375(3) . ? C11 C16 1.376(3) . ? C12 C13 1.366(3) . ? C12 H12A 0.9300 . ? C13 C14 1.399(3) . ? C13 H13A 0.9300 . ? C14 C15 1.380(3) . ? C14 C17 1.469(3) . ? C15 C16 1.382(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 123(2) . . ? N11 Cl1 O12 63.6(19) . . ? O11 Cl1 O12 170.5(8) . . ? N11 Cl1 C1 22.6(18) . . ? O11 Cl1 C1 100.5(8) . . ? O12 Cl1 C1 86.2(2) . . ? Cl1 N11 O12 90.9(18) . . ? Cl1 N11 O11 34.4(17) . . ? O12 N11 O11 125.0(8) . . ? Cl1 N11 C1 148(3) . . ? O12 N11 C1 120.9(9) . . ? O11 N11 C1 114.1(10) . . ? Cl1 O11 N11 22.8(8) . . ? N11 O12 Cl1 25.5(4) . . ? N11 C1 C2 114.8(6) . . ? N11 C1 C6 123.3(6) . . ? C2 C1 C6 121.9(2) . . ? N11 C1 Cl1 9.2(8) . . ? C2 C1 Cl1 124.0(3) . . ? C6 C1 Cl1 114.1(3) . . ? C3 C2 C1 119.1(2) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.4(2) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.5(2) . . ? C5 C4 C7 119.59(19) . . ? C3 C4 C7 122.9(2) . . ? C4 C5 C6 122.4(2) . . ? C4 C5 H5A 118.8 . . ? C6 C5 H5A 118.8 . . ? C1 C6 C5 117.8(2) . . ? C1 C6 H6A 121.1 . . ? C5 C6 H6A 121.1 . . ? C17 C7 C4 126.8(3) . . ? C17 C7 H7A 116.6 . . ? C4 C7 H7A 116.6 . . ? N1 Cl11 O1 123(2) . . ? N1 Cl11 O2 63.6(19) . . ? O1 Cl11 O2 170.5(8) . . ? N1 Cl11 C11 22.6(18) . . ? O1 Cl11 C11 100.5(8) . . ? O2 Cl11 C11 86.2(2) . . ? Cl11 N1 O2 90.9(18) . . ? Cl11 N1 O1 34.4(17) . . ? O2 N1 O1 125.0(8) . . ? Cl11 N1 C11 148(3) . . ? O2 N1 C11 120.9(9) . . ? O1 N1 C11 114.1(10) . . ? Cl11 O1 N1 22.8(8) . . ? N1 O2 Cl11 25.5(4) . . ? N1 C11 C12 114.8(6) . . ? N1 C11 C16 123.3(6) . . ? C12 C11 C16 121.9(2) . . ? N1 C11 Cl11 9.2(8) . . ? C12 C11 Cl11 124.0(3) . . ? C16 C11 Cl11 114.1(3) . . ? C13 C12 C11 119.1(2) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 121.4(2) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C15 C14 C13 117.5(2) . . ? C15 C14 C17 119.59(19) . . ? C13 C14 C17 122.9(2) . . ? C14 C15 C16 122.4(2) . . ? C14 C15 H15A 118.8 . . ? C16 C15 H15A 118.8 . . ? C11 C16 C15 117.8(2) . . ? C11 C16 H16A 121.1 . . ? C15 C16 H16A 121.1 . . ? C7 C17 C14 126.8(3) . . ? C7 C17 H17A 116.6 . . ? C14 C17 H17A 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 171.9(12) . . . . ? C1 Cl1 N11 O12 -177(4) . . . . ? O12 Cl1 N11 O11 -171.9(12) . . . . ? C1 Cl1 N11 O11 12(5) . . . . ? O11 Cl1 N11 C1 -12(5) . . . . ? O12 Cl1 N11 C1 177(4) . . . . ? O12 Cl1 O11 N11 130(7) . . . . ? C1 Cl1 O11 N11 -4(2) . . . . ? O12 N11 O11 Cl1 -9.9(15) . . . . ? C1 N11 O11 Cl1 173(3) . . . . ? O11 N11 O12 Cl1 5.6(9) . . . . ? C1 N11 O12 Cl1 -178(3) . . . . ? O11 Cl1 O12 N11 -134(6) . . . . ? C1 Cl1 O12 N11 1.3(17) . . . . ? Cl1 N11 C1 C2 -174(4) . . . . ? O12 N11 C1 C2 2.5(13) . . . . ? O11 N11 C1 C2 179.4(9) . . . . ? Cl1 N11 C1 C6 7(5) . . . . ? O12 N11 C1 C6 -176.5(7) . . . . ? O11 N11 C1 C6 0.3(14) . . . . ? O12 N11 C1 Cl1 176(5) . . . . ? O11 N11 C1 Cl1 -7(3) . . . . ? O11 Cl1 C1 N11 170(5) . . . . ? O12 Cl1 C1 N11 -3(4) . . . . ? N11 Cl1 C1 C2 7(4) . . . . ? O11 Cl1 C1 C2 177.3(7) . . . . ? O12 Cl1 C1 C2 4.0(4) . . . . ? N11 Cl1 C1 C6 -173(4) . . . . ? O11 Cl1 C1 C6 -3.0(8) . . . . ? O12 Cl1 C1 C6 -176.2(3) . . . . ? N11 C1 C2 C3 -179.7(6) . . . . ? C6 C1 C2 C3 -0.7(3) . . . . ? Cl1 C1 C2 C3 179.0(3) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C2 C3 C4 C7 179.80(19) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C7 C4 C5 C6 179.94(19) . . . . ? N11 C1 C6 C5 179.3(6) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? Cl1 C1 C6 C5 -179.4(2) . . . . ? C4 C5 C6 C1 -0.4(3) . . . . ? C5 C4 C7 C17 175.8(3) . . . . ? C3 C4 C7 C17 -4.9(4) . . . . ? O1 Cl11 N1 O2 -171.9(12) . . . . ? C11 Cl11 N1 O2 177(4) . . . . ? O2 Cl11 N1 O1 171.9(12) . . . . ? C11 Cl11 N1 O1 -12(5) . . . . ? O1 Cl11 N1 C11 12(5) . . . . ? O2 Cl11 N1 C11 -177(4) . . . . ? O2 Cl11 O1 N1 -130(7) . . . . ? C11 Cl11 O1 N1 4(2) . . . . ? O2 N1 O1 Cl11 9.9(15) . . . . ? C11 N1 O1 Cl11 -173(3) . . . . ? O1 N1 O2 Cl11 -5.6(9) . . . . ? C11 N1 O2 Cl11 178(3) . . . . ? O1 Cl11 O2 N1 134(6) . . . . ? C11 Cl11 O2 N1 -1.3(17) . . . . ? Cl11 N1 C11 C12 174(4) . . . . ? O2 N1 C11 C12 -2.5(13) . . . . ? O1 N1 C11 C12 -179.4(9) . . . . ? Cl11 N1 C11 C16 -7(5) . . . . ? O2 N1 C11 C16 176.5(7) . . . . ? O1 N1 C11 C16 -0.3(14) . . . . ? O2 N1 C11 Cl11 -176(5) . . . . ? O1 N1 C11 Cl11 7(3) . . . . ? O1 Cl11 C11 N1 -170(5) . . . . ? O2 Cl11 C11 N1 3(4) . . . . ? N1 Cl11 C11 C12 -7(4) . . . . ? O1 Cl11 C11 C12 -177.3(7) . . . . ? O2 Cl11 C11 C12 -4.0(4) . . . . ? N1 Cl11 C11 C16 173(4) . . . . ? O1 Cl11 C11 C16 3.0(8) . . . . ? O2 Cl11 C11 C16 176.2(3) . . . . ? N1 C11 C12 C13 179.7(6) . . . . ? C16 C11 C12 C13 0.7(3) . . . . ? Cl11 C11 C12 C13 -179.0(3) . . . . ? C11 C12 C13 C14 -0.9(3) . . . . ? C12 C13 C14 C15 0.9(3) . . . . ? C12 C13 C14 C17 -179.80(19) . . . . ? C13 C14 C15 C16 -0.6(3) . . . . ? C17 C14 C15 C16 -179.94(19) . . . . ? N1 C11 C16 C15 -179.3(6) . . . . ? C12 C11 C16 C15 -0.4(3) . . . . ? Cl11 C11 C16 C15 179.4(2) . . . . ? C14 C15 C16 C11 0.4(3) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.8(3) . . . . ? C13 C14 C17 C7 4.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.884 _diffrn_reflns_theta_full 27.79 _diffrn_measured_fraction_theta_full 0.884 _refine_diff_density_max 0.104 _refine_diff_density_min -0.092 _refine_diff_density_rms 0.024 # start Validation Reply Form _vrf_SYMMG02_CNS-MeOH-small-P21_c ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This pseudo P21/c model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-MeOH-small-P21_c ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.88 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; # end Validation Reply Form #===END data_CNS-MeOH-small-P21 _database_code_depnum_ccdc_archive 'CCDC 761241' #TrackingRef 'Behrndnr-CIF-CNS.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl N O2' _chemical_formula_sum 'C14 H10 Cl N O2' _chemical_formula_weight 259.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9239(3) _cell_length_b 12.9707(9) _cell_length_c 12.2375(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.236(3) _cell_angle_gamma 90.00 _cell_volume 621.84(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3493 _cell_measurement_theta_min 3.141 _cell_measurement_theta_max 22.9775 _exptl_crystal_description 'prismatic rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.497814 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3481 _diffrn_reflns_av_R_equivalents 0.0100 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.79 _reflns_number_total 2510 _reflns_number_gt 1326 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0222P)^2^+0.2256P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(2) _refine_ls_number_reflns 2510 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1110 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 0.932 _refine_ls_restrained_S_all 0.932 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3672(8) -0.46022(13) -0.1750(3) 0.1122(12) Uani 0.388(2) 1 d P . . N11 N 0.371(2) -0.4154(4) -0.1745(8) 0.0888(18) Uani 0.612(2) 1 d P . . O11 O 0.3142(15) -0.4973(3) -0.1237(4) 0.1236(19) Uani 0.612(2) 1 d P . . O12 O 0.5000(9) -0.4129(2) -0.2585(3) 0.1144(11) Uani 0.612(2) 1 d P . . C1 C 0.2616(4) -0.32922(15) -0.12324(16) 0.0740(5) Uani 1 1 d . . . C2 C 0.3154(4) -0.23904(16) -0.17935(15) 0.0814(5) Uani 1 1 d . . . H2A H 0.4134 -0.2404 -0.2468 0.098 Uiso 1 1 calc R . . C3 C 0.2223(4) -0.14768(14) -0.13430(15) 0.0775(5) Uani 1 1 d . . . H3A H 0.2559 -0.0868 -0.1724 0.093 Uiso 1 1 calc R . . C4 C 0.0784(4) -0.14298(13) -0.03282(13) 0.0665(5) Uani 1 1 d . . . C5 C 0.0288(4) -0.23573(14) 0.02071(15) 0.0742(5) Uani 1 1 d . . . H5A H -0.0688 -0.2348 0.0882 0.089 Uiso 1 1 calc R . . C6 C 0.1192(4) -0.32915(14) -0.02283(15) 0.0784(5) Uani 1 1 d . . . H6A H 0.0852 -0.3904 0.0145 0.094 Uiso 1 1 calc R . . C7 C -0.0237(4) -0.04635(11) 0.01829(15) 0.0734(5) Uani 1 1 d . . . H7A H -0.1335 -0.0520 0.0834 0.088 Uiso 1 1 calc R . . Cl11 Cl -0.3672(8) 0.46022(13) 0.1750(3) 0.1122(12) Uani 0.612(2) 1 d P . . N1 N -0.371(2) 0.4154(4) 0.1745(8) 0.0888(18) Uani 0.388(2) 1 d P . . O1 O -0.3142(15) 0.4973(3) 0.1237(4) 0.1236(19) Uani 0.388(2) 1 d P . . O2 O -0.5000(9) 0.4129(2) 0.2585(3) 0.1144(11) Uani 0.388(2) 1 d P . . C11 C -0.2616(4) 0.32922(15) 0.12324(16) 0.0740(5) Uani 1 1 d . . . C12 C -0.3154(4) 0.23904(16) 0.17935(15) 0.0814(5) Uani 1 1 d . . . H12A H -0.4134 0.2404 0.2468 0.098 Uiso 1 1 calc R . . C13 C -0.2223(4) 0.14768(14) 0.13430(15) 0.0775(5) Uani 1 1 d . . . H13A H -0.2559 0.0868 0.1724 0.093 Uiso 1 1 calc R . . C14 C -0.0784(4) 0.14298(13) 0.03282(13) 0.0665(5) Uani 1 1 d . . . C15 C -0.0288(4) 0.23573(14) -0.02071(15) 0.0742(5) Uani 1 1 d . . . H15A H 0.0688 0.2348 -0.0882 0.089 Uiso 1 1 calc R . . C16 C -0.1192(4) 0.32915(14) 0.02283(15) 0.0784(5) Uani 1 1 d . . . H16A H -0.0852 0.3904 -0.0145 0.094 Uiso 1 1 calc R . . C17 C 0.0237(4) 0.04635(11) -0.01829(15) 0.0734(5) Uani 1 1 d . . . H17A H 0.1335 0.0520 -0.0834 0.088 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1150(14) 0.091(2) 0.131(2) -0.039(2) 0.0099(14) 0.0179(19) N11 0.085(3) 0.063(4) 0.116(5) 0.008(4) -0.014(3) -0.005(4) O11 0.165(4) 0.071(3) 0.138(4) 0.010(2) 0.039(3) 0.013(2) O12 0.155(3) 0.093(2) 0.098(2) -0.0262(19) 0.038(2) 0.0151(19) C1 0.0607(11) 0.0822(14) 0.0785(13) -0.0145(11) -0.0012(9) 0.0057(10) C2 0.0708(12) 0.1065(15) 0.0676(12) -0.0035(11) 0.0111(10) -0.0007(11) C3 0.0696(11) 0.0864(13) 0.0768(13) 0.0085(11) 0.0078(10) -0.0030(10) C4 0.0535(9) 0.0791(12) 0.0668(12) -0.0047(9) 0.0025(8) 0.0012(8) C5 0.0711(11) 0.0852(13) 0.0669(11) 0.0025(10) 0.0094(9) -0.0012(10) C6 0.0755(12) 0.0781(13) 0.0817(14) 0.0031(10) 0.0052(10) 0.0014(10) C7 0.0636(10) 0.0836(13) 0.0730(12) 0.0048(10) 0.0050(9) -0.0029(10) Cl11 0.1150(14) 0.091(2) 0.131(2) -0.039(2) 0.0099(14) 0.0179(19) N1 0.085(3) 0.063(4) 0.116(5) 0.008(4) -0.014(3) -0.005(4) O1 0.165(4) 0.071(3) 0.138(4) 0.010(2) 0.039(3) 0.013(2) O2 0.155(3) 0.093(2) 0.098(2) -0.0262(19) 0.038(2) 0.0151(19) C11 0.0607(11) 0.0822(14) 0.0785(13) -0.0145(11) -0.0012(9) 0.0057(10) C12 0.0708(12) 0.1065(15) 0.0676(12) -0.0035(11) 0.0111(10) -0.0007(11) C13 0.0696(11) 0.0864(13) 0.0768(13) 0.0085(11) 0.0078(10) -0.0030(10) C14 0.0535(9) 0.0791(12) 0.0668(12) -0.0047(9) 0.0025(8) 0.0012(8) C15 0.0711(11) 0.0852(13) 0.0669(11) 0.0025(10) 0.0094(9) -0.0012(10) C16 0.0755(12) 0.0781(13) 0.0817(14) 0.0031(10) 0.0052(10) 0.0014(10) C17 0.0636(10) 0.0836(13) 0.0730(12) 0.0048(10) 0.0050(9) -0.0029(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 N11 0.581(6) . ? Cl1 O11 0.826(4) . ? Cl1 O12 1.324(4) . ? Cl1 C1 1.868(2) . ? N11 O12 1.171(9) . ? N11 O11 1.256(10) . ? N11 C1 1.364(6) . ? C1 C2 1.378(2) . ? C1 C6 1.378(2) . ? C2 C3 1.365(2) . ? C2 H2A 0.9300 . ? C3 C4 1.394(2) . ? C3 H3A 0.9300 . ? C4 C5 1.389(2) . ? C4 C7 1.467(2) . ? C5 C6 1.378(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C17 1.300(3) . ? C7 H7A 0.9300 . ? Cl11 N1 0.581(6) . ? Cl11 O1 0.826(4) . ? Cl11 O2 1.324(4) . ? Cl11 C11 1.868(2) . ? N1 O2 1.171(9) . ? N1 O1 1.256(10) . ? N1 C11 1.364(6) . ? C11 C12 1.378(2) . ? C11 C16 1.378(2) . ? C12 C13 1.365(2) . ? C12 H12A 0.9300 . ? C13 C14 1.394(2) . ? C13 H13A 0.9300 . ? C14 C15 1.389(2) . ? C14 C17 1.467(2) . ? C15 C16 1.378(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cl1 O11 125.5(14) . . ? N11 Cl1 O12 62.2(11) . . ? O11 Cl1 O12 169.4(5) . . ? N11 Cl1 C1 25.0(11) . . ? O11 Cl1 C1 101.6(5) . . ? O12 Cl1 C1 86.81(18) . . ? Cl1 N11 O12 91.8(12) . . ? Cl1 N11 O11 32.4(10) . . ? O12 N11 O11 123.8(6) . . ? Cl1 N11 C1 144.7(15) . . ? O12 N11 C1 122.9(6) . . ? O11 N11 C1 113.3(7) . . ? Cl1 O11 N11 22.1(5) . . ? N11 O12 Cl1 26.0(3) . . ? N11 C1 C2 113.9(4) . . ? N11 C1 C6 124.4(4) . . ? C2 C1 C6 121.64(18) . . ? N11 C1 Cl1 10.4(4) . . ? C2 C1 Cl1 124.04(19) . . ? C6 C1 Cl1 114.32(19) . . ? C3 C2 C1 118.91(17) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 121.91(18) . . ? C2 C3 H3A 119.0 . . ? C4 C3 H3A 119.0 . . ? C5 C4 C3 117.19(17) . . ? C5 C4 C7 119.35(16) . . ? C3 C4 C7 123.46(18) . . ? C4 C5 C6 122.22(17) . . ? C4 C5 H5A 118.9 . . ? C6 C5 H5A 118.9 . . ? C1 C6 C5 118.13(18) . . ? C1 C6 H6A 120.9 . . ? C5 C6 H6A 120.9 . . ? C17 C7 C4 126.6(2) . . ? C17 C7 H7A 116.7 . . ? C4 C7 H7A 116.7 . . ? N1 Cl11 O1 125.5(14) . . ? N1 Cl11 O2 62.2(11) . . ? O1 Cl11 O2 169.4(5) . . ? N1 Cl11 C11 25.0(11) . . ? O1 Cl11 C11 101.6(5) . . ? O2 Cl11 C11 86.81(18) . . ? Cl11 N1 O2 91.8(12) . . ? Cl11 N1 O1 32.4(10) . . ? O2 N1 O1 123.8(6) . . ? Cl11 N1 C11 144.7(15) . . ? O2 N1 C11 122.9(6) . . ? O1 N1 C11 113.3(7) . . ? Cl11 O1 N1 22.1(5) . . ? N1 O2 Cl11 26.0(3) . . ? N1 C11 C12 113.9(4) . . ? N1 C11 C16 124.4(4) . . ? C12 C11 C16 121.64(18) . . ? N1 C11 Cl11 10.4(4) . . ? C12 C11 Cl11 124.04(19) . . ? C16 C11 Cl11 114.32(19) . . ? C13 C12 C11 118.91(17) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C14 121.91(18) . . ? C12 C13 H13A 119.0 . . ? C14 C13 H13A 119.0 . . ? C15 C14 C13 117.19(17) . . ? C15 C14 C17 119.35(16) . . ? C13 C14 C17 123.46(18) . . ? C14 C15 C16 122.22(17) . . ? C14 C15 H15A 118.9 . . ? C16 C15 H15A 118.9 . . ? C11 C16 C15 118.13(18) . . ? C11 C16 H16A 120.9 . . ? C15 C16 H16A 120.9 . . ? C7 C17 C14 126.6(2) . . ? C7 C17 H17A 116.7 . . ? C14 C17 H17A 116.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cl1 N11 O12 171.4(8) . . . . ? C1 Cl1 N11 O12 -170(3) . . . . ? O12 Cl1 N11 O11 -171.4(8) . . . . ? C1 Cl1 N11 O11 19(3) . . . . ? O11 Cl1 N11 C1 -19(3) . . . . ? O12 Cl1 N11 C1 170(3) . . . . ? O12 Cl1 O11 N11 134(4) . . . . ? C1 Cl1 O11 N11 -7.9(14) . . . . ? O12 N11 O11 Cl1 -10.4(10) . . . . ? C1 N11 O11 Cl1 168(2) . . . . ? O11 N11 O12 Cl1 5.5(6) . . . . ? C1 N11 O12 Cl1 -173.1(19) . . . . ? O11 Cl1 O12 N11 -138(4) . . . . ? C1 Cl1 O12 N11 4.2(12) . . . . ? Cl1 N11 C1 C2 -168(2) . . . . ? O12 N11 C1 C2 0.2(10) . . . . ? O11 N11 C1 C2 -178.6(6) . . . . ? Cl1 N11 C1 C6 14(3) . . . . ? O12 N11 C1 C6 -177.8(6) . . . . ? O11 N11 C1 C6 3.4(10) . . . . ? O12 N11 C1 Cl1 168(3) . . . . ? O11 N11 C1 Cl1 -11(2) . . . . ? O11 Cl1 C1 N11 165(3) . . . . ? O12 Cl1 C1 N11 -9(3) . . . . ? N11 Cl1 C1 C2 13(3) . . . . ? O11 Cl1 C1 C2 178.0(5) . . . . ? O12 Cl1 C1 C2 4.6(3) . . . . ? N11 Cl1 C1 C6 -167(3) . . . . ? O11 Cl1 C1 C6 -2.6(6) . . . . ? O12 Cl1 C1 C6 -176.1(2) . . . . ? N11 C1 C2 C3 -178.6(4) . . . . ? C6 C1 C2 C3 -0.5(3) . . . . ? Cl1 C1 C2 C3 178.81(19) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C2 C3 C4 C5 -0.8(2) . . . . ? C2 C3 C4 C7 179.82(16) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C7 C4 C5 C6 -179.97(16) . . . . ? N11 C1 C6 C5 178.2(5) . . . . ? C2 C1 C6 C5 0.3(3) . . . . ? Cl1 C1 C6 C5 -179.05(18) . . . . ? C4 C5 C6 C1 -0.4(3) . . . . ? C5 C4 C7 C17 175.8(2) . . . . ? C3 C4 C7 C17 -4.9(3) . . . . ? O1 Cl11 N1 O2 -171.4(8) . . . . ? C11 Cl11 N1 O2 170(3) . . . . ? O2 Cl11 N1 O1 171.4(8) . . . . ? C11 Cl11 N1 O1 -19(3) . . . . ? O1 Cl11 N1 C11 19(3) . . . . ? O2 Cl11 N1 C11 -170(3) . . . . ? O2 Cl11 O1 N1 -134(4) . . . . ? C11 Cl11 O1 N1 7.9(14) . . . . ? O2 N1 O1 Cl11 10.4(10) . . . . ? C11 N1 O1 Cl11 -168(2) . . . . ? O1 N1 O2 Cl11 -5.5(6) . . . . ? C11 N1 O2 Cl11 173.1(19) . . . . ? O1 Cl11 O2 N1 138(4) . . . . ? C11 Cl11 O2 N1 -4.2(12) . . . . ? Cl11 N1 C11 C12 168(2) . . . . ? O2 N1 C11 C12 -0.2(10) . . . . ? O1 N1 C11 C12 178.6(6) . . . . ? Cl11 N1 C11 C16 -14(3) . . . . ? O2 N1 C11 C16 177.8(6) . . . . ? O1 N1 C11 C16 -3.4(10) . . . . ? O2 N1 C11 Cl11 -168(3) . . . . ? O1 N1 C11 Cl11 11(2) . . . . ? O1 Cl11 C11 N1 -165(3) . . . . ? O2 Cl11 C11 N1 9(3) . . . . ? N1 Cl11 C11 C12 -13(3) . . . . ? O1 Cl11 C11 C12 -178.0(5) . . . . ? O2 Cl11 C11 C12 -4.6(3) . . . . ? N1 Cl11 C11 C16 167(3) . . . . ? O1 Cl11 C11 C16 2.6(6) . . . . ? O2 Cl11 C11 C16 176.1(2) . . . . ? N1 C11 C12 C13 178.6(4) . . . . ? C16 C11 C12 C13 0.5(3) . . . . ? Cl11 C11 C12 C13 -178.81(19) . . . . ? C11 C12 C13 C14 -0.7(3) . . . . ? C12 C13 C14 C15 0.8(2) . . . . ? C12 C13 C14 C17 -179.82(16) . . . . ? C13 C14 C15 C16 -0.6(2) . . . . ? C17 C14 C15 C16 179.97(16) . . . . ? N1 C11 C16 C15 -178.2(5) . . . . ? C12 C11 C16 C15 -0.3(3) . . . . ? Cl11 C11 C16 C15 179.05(18) . . . . ? C14 C15 C16 C11 0.4(3) . . . . ? C4 C7 C17 C14 180.0 . . . . ? C15 C14 C17 C7 -175.8(2) . . . . ? C13 C14 C17 C7 4.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 27.79 _diffrn_measured_fraction_theta_full 0.921 _refine_diff_density_max 0.097 _refine_diff_density_min -0.099 _refine_diff_density_rms 0.023 # start Validation Reply Form _vrf_SYMMG02_CNS-MeOH-small-P21 ; PROBLEM: The _symmetry_equiv_pos_as_xyz values are inconsistent RESPONSE: This P21 model was generated from a proper P21/c model. ; _vrf_PLAT029_CNS-MeOH-small-P21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.92 RESPONSE: The crystal was small and only weakly diffracting. Nevertheless, the structure is refined with reasonably standard uncertainties, the ratio of parameter to observed reflection is about 1:25. ; # end Validation Reply Form #===END