# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Florence Mongin' _publ_contact_author_address ; Campus scientifique de Beaulieu SESO, UMR CNRS 6510, Universite de Rennes 1 Batiment 10A, Case 1003 RENNES Cedex 35042 FRANCE ; _publ_contact_author_email FLORENCE.MONGIN@UNIV-RENNES1.FR _publ_section_title ; 1,3-Dipolar cycloaddition of ketones with electrophilically activated carbonyl ylides. Synthesis of spirocyclic dioxolane indolinones ; loop_ _publ_author_name 'Florence Mongin' 'Ghenia Bentabed-Ababsa' 'Aicha Derdour' L.Domingo 'Thierry Roisnel' ; J.A.Saez ; data_5a _database_code_depnum_ccdc_archive 'CCDC 633367' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H13 N3 O4' _chemical_formula_weight 347.32 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.989(2) _cell_length_b 10.7196(10) _cell_length_c 13.1319(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.847(9) _cell_angle_gamma 90.00 _cell_volume 1667.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Saphire 3 Xcalibur' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 19.64 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13272 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_sigmaI/netI 0.3123 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 31.90 _reflns_number_total 4892 _reflns_number_gt 1178 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.26' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26' _computing_structure_solution 'SIR-97_(Altomare & al., 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON_(Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0728P)^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 SHELXL _refine_ls_extinction_coef 0.0039(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4892 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2292 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1403 _refine_ls_wR_factor_gt 0.1232 _refine_ls_goodness_of_fit_ref 0.628 _refine_ls_restrained_S_all 0.628 _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 C1 C -0.2310(2) 0.0312(2) 0.6087(2) 0.0477(7) Uani 1 1 d . . . C2 C -0.3339(2) -0.0199(2) 0.5729(2) 0.0603(8) Uani 1 1 d . . . H2 H -0.3505 -0.0503 0.5060 0.072 Uiso 1 1 calc R . . C3 C -0.4122(3) -0.0248(3) 0.6395(3) 0.0697(9) Uani 1 1 d . . . H3 H -0.4827 -0.0598 0.6171 0.084 Uiso 1 1 calc R . . C4 C -0.3880(2) 0.0213(3) 0.7391(3) 0.0685(9) Uani 1 1 d . . . H4 H -0.4414 0.0156 0.7832 0.082 Uiso 1 1 calc R . . C5 C -0.2846(2) 0.0756(2) 0.7728(2) 0.0609(8) Uani 1 1 d . . . H5 H -0.2684 0.1073 0.8393 0.073 Uiso 1 1 calc R . . C6 C -0.2060(2) 0.0824(2) 0.70745(19) 0.0463(6) Uani 1 1 d . . . C7 C -0.0909(2) 0.1382(2) 0.71782(19) 0.0477(7) Uani 1 1 d . . . C8 C -0.0485(3) 0.0928(2) 0.61873(19) 0.0496(7) Uani 1 1 d . . . C9 C -0.0866(2) 0.2861(2) 0.72338(19) 0.0495(7) Uani 1 1 d . . . C10 C 0.0423(2) 0.2125(2) 0.85415(19) 0.0545(7) Uani 1 1 d . . . H10 H 0.0089 0.2349 0.9152 0.065 Uiso 1 1 calc R . . C11 C 0.1654(2) 0.1942(2) 0.8835(2) 0.0500(7) Uani 1 1 d . . . C12 C 0.2351(3) 0.1820(2) 0.8090(2) 0.0647(8) Uani 1 1 d . . . H12 H 0.2032 0.1834 0.7398 0.078 Uiso 1 1 calc R . . C13 C 0.3490(3) 0.1680(3) 0.8344(3) 0.0724(9) Uani 1 1 d . . . H13 H 0.3943 0.1609 0.7832 0.087 Uiso 1 1 calc R . . C14 C 0.3965(2) 0.1646(2) 0.9379(3) 0.0621(8) Uani 1 1 d . . . C15 C 0.3296(2) 0.1732(2) 1.0134(2) 0.0613(8) Uani 1 1 d . . . H15 H 0.3615 0.1690 1.0826 0.074 Uiso 1 1 calc R . . C16 C 0.2134(2) 0.1882(2) 0.9856(2) 0.0572(7) Uani 1 1 d . . . H16 H 0.1677 0.1943 1.0366 0.069 Uiso 1 1 calc R . . C17 C 0.5688(3) 0.1684(3) 1.0580(3) 0.0910(10) Uani 1 1 d . . . H17A H 0.6485 0.1584 1.0587 0.136 Uiso 1 1 calc R . . H17B H 0.5426 0.1063 1.1014 0.136 Uiso 1 1 calc R . . H17C H 0.5540 0.2499 1.0830 0.136 Uiso 1 1 calc R . . C18 C -0.1752(3) 0.3379(2) 0.7797(2) 0.0576(7) Uani 1 1 d . . . C19 C -0.0997(2) 0.3433(2) 0.6210(2) 0.0528(7) Uani 1 1 d . . . N1 N -0.13594(19) 0.03920(18) 0.55907(16) 0.0523(6) Uani 1 1 d . . . H1 H -0.1340 0.0128 0.4975 0.063 Uiso 1 1 calc R . . N2 N -0.2429(2) 0.3790(2) 0.8238(2) 0.0832(8) Uani 1 1 d . . . N3 N -0.1164(2) 0.3797(2) 0.5390(2) 0.0750(8) Uani 1 1 d . . . O1 O 0.04787(16) 0.10596(16) 0.60001(13) 0.0636(5) Uani 1 1 d . . . O2 O -0.01386(14) 0.10439(15) 0.80575(12) 0.0554(5) Uani 1 1 d . . . O3 O 0.02090(14) 0.31021(14) 0.77797(12) 0.0539(5) Uani 1 1 d . . . O4 O 0.51137(17) 0.15418(19) 0.95532(18) 0.0866(7) Uani 1 1 d . . . 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 C1 0.0525(18) 0.0408(15) 0.0487(18) 0.0010(13) 0.0046(15) -0.0004(13) C2 0.058(2) 0.0495(17) 0.069(2) -0.0072(15) -0.0038(17) 0.0009(15) C3 0.056(2) 0.0545(18) 0.095(3) 0.0056(18) 0.000(2) -0.0017(15) C4 0.065(2) 0.068(2) 0.076(2) 0.0087(18) 0.0217(18) -0.0021(17) C5 0.065(2) 0.0569(18) 0.0611(18) -0.0023(15) 0.0115(17) -0.0012(16) C6 0.0464(17) 0.0472(15) 0.0461(17) 0.0006(13) 0.0092(14) 0.0002(13) C7 0.0568(18) 0.0429(15) 0.0418(16) -0.0047(12) 0.0028(14) 0.0014(13) C8 0.0594(19) 0.0393(15) 0.0511(18) -0.0011(13) 0.0120(16) 0.0035(15) C9 0.0532(17) 0.0440(15) 0.0485(17) -0.0066(13) -0.0012(15) 0.0039(13) C10 0.066(2) 0.0508(16) 0.0447(16) -0.0057(14) 0.0019(14) 0.0013(15) C11 0.0479(17) 0.0492(16) 0.0510(18) -0.0036(13) 0.0017(15) 0.0006(13) C12 0.063(2) 0.067(2) 0.061(2) -0.0060(15) 0.0015(17) 0.0047(16) C13 0.071(2) 0.073(2) 0.070(2) -0.0043(17) -0.0001(18) 0.0105(17) C14 0.0496(19) 0.0496(16) 0.085(2) -0.0051(16) 0.0037(19) 0.0067(14) C15 0.066(2) 0.0541(17) 0.0584(19) 0.0027(14) -0.0072(17) 0.0072(15) C16 0.060(2) 0.0583(18) 0.0527(18) -0.0021(14) 0.0061(15) -0.0013(15) C17 0.067(2) 0.091(2) 0.106(3) -0.002(2) -0.018(2) 0.0019(18) C18 0.068(2) 0.0500(16) 0.0521(18) -0.0034(14) 0.0004(16) 0.0038(16) C19 0.0646(19) 0.0431(15) 0.0506(19) -0.0042(15) 0.0080(16) 0.0046(14) N1 0.0645(15) 0.0500(13) 0.0406(13) -0.0103(10) 0.0027(12) -0.0036(12) N2 0.089(2) 0.0791(19) 0.085(2) -0.0158(15) 0.0255(16) 0.0143(15) N3 0.099(2) 0.0638(17) 0.0625(17) 0.0069(14) 0.0130(15) 0.0077(13) O1 0.0639(13) 0.0630(12) 0.0672(13) -0.0130(10) 0.0209(10) -0.0015(11) O2 0.0671(12) 0.0459(10) 0.0475(11) 0.0016(9) -0.0094(9) -0.0038(9) O3 0.0606(12) 0.0442(11) 0.0533(12) -0.0026(9) -0.0032(10) 0.0023(9) O4 0.0593(15) 0.0994(16) 0.0972(17) -0.0052(13) 0.0000(13) 0.0092(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 C1 C2 1.365(3) . ? C1 C6 1.398(3) . ? C1 N1 1.400(3) . ? C2 C3 1.379(4) . ? C2 H2 0.9300 . ? C3 C4 1.387(4) . ? C3 H3 0.9300 . ? C4 C5 1.378(4) . ? C4 H4 0.9300 . ? C5 C6 1.371(3) . ? C5 H5 0.9300 . ? C6 C7 1.490(3) . ? C7 O2 1.411(3) . ? C7 C8 1.547(3) . ? C7 C9 1.587(3) . ? C8 O1 1.226(3) . ? C8 N1 1.338(3) . ? C9 O3 1.399(3) . ? C9 C19 1.464(4) . ? C9 C18 1.492(4) . ? C10 O2 1.438(3) . ? C10 O3 1.444(3) . ? C10 C11 1.480(3) . ? C10 H10 0.9800 . ? C11 C16 1.377(3) . ? C11 C12 1.387(3) . ? C12 C13 1.363(4) . ? C12 H12 0.9300 . ? C13 C14 1.392(4) . ? C13 H13 0.9300 . ? C14 O4 1.366(3) . ? C14 C15 1.370(4) . ? C15 C16 1.395(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 O4 1.424(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 N2 1.154(3) . ? C19 N3 1.134(3) . ? N1 H1 0.8600 . ? 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 C2 C1 C6 122.1(3) . . ? C2 C1 N1 128.4(3) . . ? C6 C1 N1 109.5(2) . . ? C1 C2 C3 117.7(3) . . ? C1 C2 H2 121.2 . . ? C3 C2 H2 121.2 . . ? C2 C3 C4 121.4(3) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 120.0(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 119.5(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 119.3(3) . . ? C5 C6 C7 132.9(3) . . ? C1 C6 C7 107.8(2) . . ? O2 C7 C6 116.9(2) . . ? O2 C7 C8 110.4(2) . . ? C6 C7 C8 102.5(2) . . ? O2 C7 C9 101.90(18) . . ? C6 C7 C9 115.4(2) . . ? C8 C7 C9 109.9(2) . . ? O1 C8 N1 127.5(2) . . ? O1 C8 C7 125.1(2) . . ? N1 C8 C7 107.4(2) . . ? O3 C9 C19 110.7(2) . . ? O3 C9 C18 110.3(2) . . ? C19 C9 C18 108.3(2) . . ? O3 C9 C7 103.27(18) . . ? C19 C9 C7 112.2(2) . . ? C18 C9 C7 112.0(2) . . ? O2 C10 O3 104.90(18) . . ? O2 C10 C11 112.9(2) . . ? O3 C10 C11 109.9(2) . . ? O2 C10 H10 109.7 . . ? O3 C10 H10 109.7 . . ? C11 C10 H10 109.7 . . ? C16 C11 C12 118.4(2) . . ? C16 C11 C10 120.7(2) . . ? C12 C11 C10 120.9(2) . . ? C13 C12 C11 121.8(3) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 119.1(3) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? O4 C14 C15 124.9(3) . . ? O4 C14 C13 114.6(3) . . ? C15 C14 C13 120.6(3) . . ? C14 C15 C16 119.3(3) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C11 C16 C15 120.8(3) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N2 C18 C9 179.2(3) . . ? N3 C19 C9 174.0(3) . . ? C8 N1 C1 112.0(2) . . ? C8 N1 H1 124.0 . . ? C1 N1 H1 124.0 . . ? C7 O2 C10 110.97(18) . . ? C9 O3 C10 105.80(18) . . ? C14 O4 C17 118.5(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 C6 C1 C2 C3 -2.9(4) . . . . ? N1 C1 C2 C3 175.3(2) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C2 C3 C4 C5 1.3(4) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C4 C5 C6 C1 -1.7(4) . . . . ? C4 C5 C6 C7 177.2(2) . . . . ? C2 C1 C6 C5 3.5(4) . . . . ? N1 C1 C6 C5 -175.0(2) . . . . ? C2 C1 C6 C7 -175.6(2) . . . . ? N1 C1 C6 C7 5.9(3) . . . . ? C5 C6 C7 O2 51.6(4) . . . . ? C1 C6 C7 O2 -129.5(2) . . . . ? C5 C6 C7 C8 172.4(3) . . . . ? C1 C6 C7 C8 -8.6(2) . . . . ? C5 C6 C7 C9 -68.2(4) . . . . ? C1 C6 C7 C9 110.7(2) . . . . ? O2 C7 C8 O1 -46.7(3) . . . . ? C6 C7 C8 O1 -171.9(2) . . . . ? C9 C7 C8 O1 64.9(3) . . . . ? O2 C7 C8 N1 133.9(2) . . . . ? C6 C7 C8 N1 8.7(2) . . . . ? C9 C7 C8 N1 -114.5(2) . . . . ? O2 C7 C9 O3 26.2(2) . . . . ? C6 C7 C9 O3 153.8(2) . . . . ? C8 C7 C9 O3 -90.9(2) . . . . ? O2 C7 C9 C19 145.4(2) . . . . ? C6 C7 C9 C19 -86.9(3) . . . . ? C8 C7 C9 C19 28.3(3) . . . . ? O2 C7 C9 C18 -92.5(2) . . . . ? C6 C7 C9 C18 35.2(3) . . . . ? C8 C7 C9 C18 150.4(2) . . . . ? O2 C10 C11 C16 -111.6(3) . . . . ? O3 C10 C11 C16 131.7(2) . . . . ? O2 C10 C11 C12 68.0(3) . . . . ? O3 C10 C11 C12 -48.7(3) . . . . ? C16 C11 C12 C13 -1.9(4) . . . . ? C10 C11 C12 C13 178.4(2) . . . . ? C11 C12 C13 C14 0.7(4) . . . . ? C12 C13 C14 O4 -178.1(2) . . . . ? C12 C13 C14 C15 1.0(4) . . . . ? O4 C14 C15 C16 177.6(2) . . . . ? C13 C14 C15 C16 -1.4(4) . . . . ? C12 C11 C16 C15 1.5(4) . . . . ? C10 C11 C16 C15 -178.9(2) . . . . ? C14 C15 C16 C11 0.2(4) . . . . ? O3 C9 C18 N2 24(23) . . . . ? C19 C9 C18 N2 -97(23) . . . . ? C7 C9 C18 N2 138(23) . . . . ? O3 C9 C19 N3 152(3) . . . . ? C18 C9 C19 N3 -87(3) . . . . ? C7 C9 C19 N3 38(3) . . . . ? O1 C8 N1 C1 175.0(2) . . . . ? C7 C8 N1 C1 -5.7(3) . . . . ? C2 C1 N1 C8 -178.4(2) . . . . ? C6 C1 N1 C8 0.0(3) . . . . ? C6 C7 O2 C10 -132.8(2) . . . . ? C8 C7 O2 C10 110.6(2) . . . . ? C9 C7 O2 C10 -6.1(2) . . . . ? O3 C10 O2 C7 -15.5(2) . . . . ? C11 C10 O2 C7 -135.1(2) . . . . ? C19 C9 O3 C10 -156.67(19) . . . . ? C18 C9 O3 C10 83.4(2) . . . . ? C7 C9 O3 C10 -36.4(2) . . . . ? O2 C10 O3 C9 33.3(2) . . . . ? C11 C10 O3 C9 154.9(2) . . . . ? C15 C14 O4 C17 -8.1(4) . . . . ? C13 C14 O4 C17 170.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.852 _diffrn_reflns_theta_full 31.90 _diffrn_measured_fraction_theta_full 0.852 _refine_diff_density_max 0.880 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.045 # Attachment 'cif mongin.cif' data_4a _database_code_depnum_ccdc_archive 'CCDC 654056' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C15 H13 Cl1 N2 O4' _chemical_formula_sum 'C15 H13 Cl N2 O4' _chemical_formula_weight 320.72 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5107(5) _cell_length_b 10.4161(8) _cell_length_c 10.9534(7) _cell_angle_alpha 111.597(3) _cell_angle_beta 96.849(3) _cell_angle_gamma 103.339(3) _cell_volume 755.25(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6940 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.44 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.41 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.897 _exptl_absorpt_correction_T_max 0.968 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_unetI/netI 0.0431 _diffrn_reflns_number 14105 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.97 _reflns_number_total 3361 _reflns_number_gt 3060 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0456P)^2^+0.4513P] 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_number_reflns 3361 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_S_all 1.146 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.465 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.068 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0846(2) 0.5981(2) 0.77586(18) 0.0170(4) Uani 1 d . . . H1 H -0.0315 0.6291 0.7706 0.02 Uiso 1 calc R . . C2 C 0.2292(2) 0.68738(19) 0.64153(18) 0.0147(4) Uani 1 d . . . C3 C 0.3532(2) 0.77260(19) 0.79057(18) 0.0153(4) Uani 1 d . . . C4 C 0.0528(2) 0.47281(19) 0.81453(18) 0.0164(4) Uani 1 d . . . C5 C -0.1273(3) 0.4064(2) 0.82030(18) 0.0179(4) Uani 1 d . . . H5 H -0.2257 0.4465 0.8073 0.021 Uiso 1 calc R . . C6 C -0.1656(3) 0.2821(2) 0.84481(19) 0.0206(4) Uani 1 d . . . H6 H -0.2889 0.2368 0.8485 0.025 Uiso 1 calc R . . C7 C -0.0189(3) 0.2255(2) 0.86383(19) 0.0200(4) Uani 1 d . . . C8 C 0.1634(3) 0.2923(2) 0.8628(2) 0.0221(4) Uani 1 d . . . H8 H 0.2625 0.2541 0.8795 0.027 Uiso 1 calc R . . C9 C 0.1988(3) 0.4158(2) 0.8370(2) 0.0212(4) Uani 1 d . . . H9 H 0.3225 0.4617 0.8347 0.025 Uiso 1 calc R . . C10 C 0.3447(2) 0.6508(2) 0.53473(18) 0.0172(4) Uani 1 d . . . C11 C 0.5967(3) 0.7542(2) 0.4558(2) 0.0246(4) Uani 1 d . . . H11A H 0.5243 0.7108 0.3612 0.03 Uiso 1 calc R . . H11B H 0.6694 0.6898 0.4675 0.03 Uiso 1 calc R . . C12 C 0.7273(3) 0.9022(3) 0.4888(2) 0.0341(5) Uani 1 d . . . H12A H 0.8149 0.8939 0.4288 0.051 Uiso 1 calc R . . H12B H 0.798 0.9441 0.5826 0.051 Uiso 1 calc R . . H12C H 0.6538 0.9648 0.4765 0.051 Uiso 1 calc R . . C13 C 0.0939(3) 0.7654(2) 0.60749(19) 0.0193(4) Uani 1 d . . . H13A H 0.0209 0.7883 0.6768 0.029 Uiso 1 calc R . . H13B H 0.0086 0.7027 0.5196 0.029 Uiso 1 calc R . . H13C H 0.1656 0.855 0.6043 0.029 Uiso 1 calc R . . C14 C 0.3920(2) 0.9316(2) 0.83750(18) 0.0172(4) Uani 1 d . . . C15 C 0.5355(3) 0.7386(2) 0.80553(18) 0.0185(4) Uani 1 d . . . N1 N 0.4207(2) 1.05389(18) 0.87010(17) 0.0228(4) Uani 1 d . . . N2 N 0.6716(2) 0.70845(19) 0.81814(18) 0.0279(4) Uani 1 d . . . O1 O 0.24401(18) 0.72012(14) 0.86801(13) 0.0186(3) Uani 1 d . . . O2 O 0.13551(17) 0.55738(13) 0.64947(12) 0.0161(3) Uani 1 d . . . O3 O 0.32175(19) 0.53206(15) 0.45091(14) 0.0239(3) Uani 1 d . . . O4 O 0.46976(18) 0.77285(14) 0.54830(13) 0.0219(3) Uani 1 d . . . Cl1 Cl -0.06573(7) 0.06710(5) 0.89026(5) 0.02613(16) Uani 1 d . . . 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 C1 0.0152(8) 0.0176(9) 0.0176(9) 0.0054(7) 0.0045(7) 0.0066(7) C2 0.0136(8) 0.0128(8) 0.0183(9) 0.0062(7) 0.0040(7) 0.0050(7) C3 0.0145(8) 0.0143(9) 0.0182(9) 0.0063(7) 0.0047(7) 0.0065(7) C4 0.0174(8) 0.0161(9) 0.0162(9) 0.0053(7) 0.0051(7) 0.0074(7) C5 0.0175(8) 0.0201(9) 0.0176(9) 0.0078(8) 0.0043(7) 0.0081(7) C6 0.0186(9) 0.0203(10) 0.0229(10) 0.0089(8) 0.0063(7) 0.0049(8) C7 0.0260(10) 0.0169(9) 0.0193(9) 0.0073(8) 0.0074(8) 0.0093(8) C8 0.0225(9) 0.0213(10) 0.0287(10) 0.0117(8) 0.0086(8) 0.0137(8) C9 0.0174(9) 0.0232(10) 0.0271(10) 0.0112(8) 0.0092(8) 0.0097(8) C10 0.0147(8) 0.0210(10) 0.0170(9) 0.0077(8) 0.0032(7) 0.0078(7) C11 0.0188(9) 0.0322(11) 0.0238(10) 0.0105(9) 0.0100(8) 0.0081(8) C12 0.0311(11) 0.0345(13) 0.0435(13) 0.0195(11) 0.0193(10) 0.0107(10) C13 0.0173(8) 0.0196(10) 0.0221(9) 0.0089(8) 0.0033(7) 0.0075(7) C14 0.0119(8) 0.0199(10) 0.0200(9) 0.0068(8) 0.0042(7) 0.0070(7) C15 0.0186(9) 0.0184(9) 0.0170(9) 0.0043(7) 0.0044(7) 0.0073(7) N1 0.0196(8) 0.0200(9) 0.0273(9) 0.0072(7) 0.0040(7) 0.0078(7) N2 0.0250(9) 0.0294(10) 0.0266(9) 0.0045(8) 0.0035(7) 0.0160(8) O1 0.0185(6) 0.0181(7) 0.0177(6) 0.0064(5) 0.0066(5) 0.0032(5) O2 0.0169(6) 0.0153(6) 0.0176(6) 0.0068(5) 0.0058(5) 0.0061(5) O3 0.0208(7) 0.0221(7) 0.0243(7) 0.0035(6) 0.0066(6) 0.0074(6) O4 0.0216(7) 0.0216(7) 0.0246(7) 0.0096(6) 0.0114(6) 0.0071(6) Cl1 0.0325(3) 0.0209(3) 0.0333(3) 0.0158(2) 0.0127(2) 0.0125(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O2 1.418(2) . ? C1 O1 1.460(2) . ? C1 C4 1.492(3) . ? C1 H1 1 . ? C2 O2 1.414(2) . ? C2 C10 1.527(2) . ? C2 C13 1.532(2) . ? C2 C3 1.584(2) . ? C3 O1 1.411(2) . ? C3 C14 1.486(3) . ? C3 C15 1.497(2) . ? C4 C5 1.390(3) . ? C4 C9 1.400(3) . ? C5 C6 1.391(3) . ? C5 H5 0.95 . ? C6 C7 1.393(3) . ? C6 H6 0.95 . ? C7 C8 1.389(3) . ? C7 Cl1 1.743(2) . ? C8 C9 1.390(3) . ? C8 H8 0.95 . ? C9 H9 0.95 . ? C10 O3 1.196(2) . ? C10 O4 1.341(2) . ? C11 O4 1.465(2) . ? C11 C12 1.509(3) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 N1 1.147(2) . ? C15 N2 1.144(2) . ? 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 O2 C1 O1 104.47(13) . . ? O2 C1 C4 109.04(14) . . ? O1 C1 C4 112.45(15) . . ? O2 C1 H1 110.2 . . ? O1 C1 H1 110.2 . . ? C4 C1 H1 110.2 . . ? O2 C2 C10 107.93(14) . . ? O2 C2 C13 112.68(14) . . ? C10 C2 C13 110.36(15) . . ? O2 C2 C3 99.45(14) . . ? C10 C2 C3 113.49(14) . . ? C13 C2 C3 112.46(14) . . ? O1 C3 C14 111.00(14) . . ? O1 C3 C15 108.29(15) . . ? C14 C3 C15 109.04(15) . . ? O1 C3 C2 103.95(14) . . ? C14 C3 C2 112.17(15) . . ? C15 C3 C2 112.25(14) . . ? C5 C4 C9 119.51(18) . . ? C5 C4 C1 119.34(16) . . ? C9 C4 C1 121.03(17) . . ? C4 C5 C6 121.02(17) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C7 118.39(18) . . ? C5 C6 H6 120.8 . . ? C7 C6 H6 120.8 . . ? C8 C7 C6 121.76(18) . . ? C8 C7 Cl1 119.24(15) . . ? C6 C7 Cl1 119.00(15) . . ? C7 C8 C9 119.00(17) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C8 C9 C4 120.26(18) . . ? C8 C9 H9 119.9 . . ? C4 C9 H9 119.9 . . ? O3 C10 O4 126.30(17) . . ? O3 C10 C2 124.64(17) . . ? O4 C10 C2 109.03(15) . . ? O4 C11 C12 107.18(16) . . ? O4 C11 H11A 110.3 . . ? C12 C11 H11A 110.3 . . ? O4 C11 H11B 110.3 . . ? C12 C11 H11B 110.3 . . ? H11A C11 H11B 108.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C14 C3 178.1(2) . . ? N2 C15 C3 177.5(2) . . ? C3 O1 C1 108.23(13) . . ? C2 O2 C1 106.26(13) . . ? C10 O4 C11 115.39(14) . . ? 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 O2 C2 C3 O1 -30.51(15) . . . . ? C10 C2 C3 O1 -144.88(15) . . . . ? C13 C2 C3 O1 88.95(17) . . . . ? O2 C2 C3 C14 -150.51(14) . . . . ? C10 C2 C3 C14 95.12(17) . . . . ? C13 C2 C3 C14 -31.1(2) . . . . ? O2 C2 C3 C15 86.30(17) . . . . ? C10 C2 C3 C15 -28.1(2) . . . . ? C13 C2 C3 C15 -154.24(16) . . . . ? O2 C1 C4 C5 -113.03(17) . . . . ? O1 C1 C4 C5 131.59(17) . . . . ? O2 C1 C4 C9 63.1(2) . . . . ? O1 C1 C4 C9 -52.3(2) . . . . ? C9 C4 C5 C6 -1.6(3) . . . . ? C1 C4 C5 C6 174.55(16) . . . . ? C4 C5 C6 C7 0.1(3) . . . . ? C5 C6 C7 C8 1.9(3) . . . . ? C5 C6 C7 Cl1 -178.33(14) . . . . ? C6 C7 C8 C9 -2.5(3) . . . . ? Cl1 C7 C8 C9 177.80(15) . . . . ? C7 C8 C9 C4 0.9(3) . . . . ? C5 C4 C9 C8 1.0(3) . . . . ? C1 C4 C9 C8 -175.03(17) . . . . ? O2 C2 C10 O3 17.2(2) . . . . ? C13 C2 C10 O3 -106.3(2) . . . . ? C3 C2 C10 O3 126.44(19) . . . . ? O2 C2 C10 O4 -164.66(14) . . . . ? C13 C2 C10 O4 71.81(18) . . . . ? C3 C2 C10 O4 -55.46(19) . . . . ? O1 C3 C14 N1 -135(5) . . . . ? C15 C3 C14 N1 106(5) . . . . ? C2 C3 C14 N1 -19(6) . . . . ? O1 C3 C15 N2 24(5) . . . . ? C14 C3 C15 N2 145(5) . . . . ? C2 C3 C15 N2 -90(5) . . . . ? C14 C3 O1 C1 129.45(15) . . . . ? C15 C3 O1 C1 -110.87(15) . . . . ? C2 C3 O1 C1 8.66(17) . . . . ? O2 C1 O1 C3 16.53(17) . . . . ? C4 C1 O1 C3 134.64(15) . . . . ? C10 C2 O2 C1 160.42(13) . . . . ? C13 C2 O2 C1 -77.47(17) . . . . ? C3 C2 O2 C1 41.83(15) . . . . ? O1 C1 O2 C2 -38.33(16) . . . . ? C4 C1 O2 C2 -158.75(14) . . . . ? O3 C10 O4 C11 -4.3(3) . . . . ? C2 C10 O4 C11 177.61(15) . . . . ? C12 C11 O4 C10 -178.92(17) . . . . ? data_13a _database_code_depnum_ccdc_archive 'CCDC 654057' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H13 N3 O3' _chemical_formula_sum 'C19 H13 N3 O3' _chemical_formula_weight 331.32 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.1376(6) _cell_length_b 9.8479(6) _cell_length_c 17.8528(13) _cell_angle_alpha 90 _cell_angle_beta 98.305(4) _cell_angle_gamma 90 _cell_volume 1589.66(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4354 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.24 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.65 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.976 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_unetI/netI 0.044 _diffrn_reflns_number 15033 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3640 _reflns_number_gt 2892 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0523P)^2^+0.4159P] 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_number_reflns 3640 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.11 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.338 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.73376(16) -0.19114(15) 0.17554(8) 0.0246(3) Uani 1 d . . . H1 H 0.6799 -0.2474 0.2094 0.03 Uiso 1 calc R . . C2 C 0.60568(16) 0.00903(14) 0.13572(8) 0.0217(3) Uani 1 d . . . C3 C 0.70236(16) 0.02360(14) 0.21665(8) 0.0225(3) Uani 1 d . . . C4 C 0.66683(16) 0.10868(15) 0.07986(8) 0.0250(3) Uani 1 d . . . C5 C 0.33050(17) -0.00751(16) 0.15957(9) 0.0279(3) Uani 1 d . . . H5 H 0.3443 -0.087 0.1899 0.033 Uiso 1 calc R . . C6 C 0.19210(17) 0.05380(17) 0.14431(9) 0.0307(4) Uani 1 d . . . H6 H 0.1105 0.0165 0.1648 0.037 Uiso 1 calc R . . C7 C 0.17299(17) 0.16869(17) 0.09954(9) 0.0313(4) Uani 1 d . . . H7 H 0.0779 0.2095 0.0901 0.038 Uiso 1 calc R . . C8 C 0.28908(17) 0.22626(16) 0.06793(9) 0.0283(3) Uani 1 d . . . H8 H 0.275 0.3046 0.0367 0.034 Uiso 1 calc R . . C9 C 0.44718(16) 0.04971(15) 0.12964(8) 0.0233(3) Uani 1 d . . . C10 C 0.42508(16) 0.16454(15) 0.08396(8) 0.0224(3) Uani 1 d . . . C11 C 0.84420(16) -0.27539(15) 0.14252(8) 0.0237(3) Uani 1 d . . . C12 C 0.93813(17) -0.21510(16) 0.09772(8) 0.0273(3) Uani 1 d . . . H12 H 0.9291 -0.121 0.0862 0.033 Uiso 1 calc R . . C13 C 1.04407(17) -0.29148(17) 0.07001(9) 0.0295(4) Uani 1 d . . . H13 H 1.1089 -0.2502 0.0397 0.035 Uiso 1 calc R . . C14 C 1.05616(18) -0.42867(17) 0.08636(8) 0.0303(4) Uani 1 d . . . H14 H 1.1305 -0.4807 0.0676 0.036 Uiso 1 calc R . . C15 C 0.96190(18) -0.49104(16) 0.12946(9) 0.0306(4) Uani 1 d . . . H15 H 0.97 -0.5857 0.1395 0.037 Uiso 1 calc R . . C16 C 0.85475(18) -0.41421(16) 0.15816(8) 0.0281(3) Uani 1 d . . . H16 H 0.7894 -0.4559 0.1881 0.034 Uiso 1 calc R . . C17 C 0.57588(19) 0.31699(17) 0.00949(10) 0.0340(4) Uani 1 d . . . H17A H 0.4826 0.3674 0 0.051 Uiso 0.5 calc PR . . H17B H 0.604 0.2868 -0.0388 0.051 Uiso 0.5 calc PR . . H17C H 0.6534 0.376 0.0355 0.051 Uiso 0.5 calc PR . . H17D H 0.6774 0.3194 -0.0022 0.051 Uiso 0.5 calc PR . . H17E H 0.556 0.4 0.0366 0.051 Uiso 0.5 calc PR . . H17F H 0.5065 0.3108 -0.0377 0.051 Uiso 0.5 calc PR . . C18 C 0.77612(17) 0.15717(16) 0.22755(8) 0.0260(3) Uani 1 d . . . C19 C 0.61234(17) 0.00398(16) 0.27927(8) 0.0275(3) Uani 1 d . . . N1 N 0.55761(14) 0.19940(13) 0.05661(7) 0.0254(3) Uani 1 d . . . N2 N 0.82478(16) 0.26427(14) 0.23453(8) 0.0355(3) Uani 1 d . . . N3 N 0.54538(17) -0.01086(16) 0.32811(8) 0.0393(4) Uani 1 d . . . O1 O 0.80814(11) -0.07936(10) 0.21688(6) 0.0246(2) Uani 1 d . . . O2 O 0.63108(11) -0.12788(10) 0.11729(6) 0.0268(3) Uani 1 d . . . O3 O 0.79117(12) 0.10679(12) 0.06333(6) 0.0315(3) Uani 1 d . . . 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 C1 0.0268(7) 0.0236(7) 0.0232(7) 0.0014(6) 0.0025(6) 0.0005(6) C2 0.0234(7) 0.0205(7) 0.0212(7) -0.0007(5) 0.0033(5) 0.0018(6) C3 0.0240(7) 0.0228(7) 0.0208(7) -0.0009(5) 0.0033(5) 0.0032(6) C4 0.0252(8) 0.0278(8) 0.0218(7) -0.0005(6) 0.0029(6) -0.0002(6) C5 0.0273(8) 0.0307(8) 0.0254(7) 0.0006(6) 0.0035(6) -0.0039(6) C6 0.0234(8) 0.0419(9) 0.0271(8) -0.0036(7) 0.0044(6) -0.0041(7) C7 0.0232(8) 0.0388(9) 0.0308(8) -0.0073(7) -0.0001(6) 0.0069(7) C8 0.0276(8) 0.0274(8) 0.0288(8) -0.0009(6) 0.0001(6) 0.0055(6) C9 0.0228(7) 0.0247(7) 0.0221(7) -0.0017(6) 0.0019(5) 0.0005(6) C10 0.0248(7) 0.0217(7) 0.0207(6) -0.0027(5) 0.0028(5) -0.0004(6) C11 0.0247(7) 0.0246(7) 0.0211(7) -0.0027(5) 0.0014(6) 0.0034(6) C12 0.0296(8) 0.0277(8) 0.0240(7) 0.0030(6) 0.0020(6) 0.0010(6) C13 0.0280(8) 0.0362(9) 0.0244(7) 0.0024(6) 0.0038(6) 0.0019(7) C14 0.0308(8) 0.0359(9) 0.0243(7) -0.0045(6) 0.0043(6) 0.0093(7) C15 0.0386(9) 0.0241(8) 0.0292(8) -0.0009(6) 0.0051(7) 0.0065(7) C16 0.0322(8) 0.0287(8) 0.0234(7) 0.0020(6) 0.0042(6) 0.0002(7) C17 0.0373(9) 0.0283(8) 0.0369(9) 0.0095(7) 0.0071(7) -0.0015(7) C18 0.0271(8) 0.0276(8) 0.0226(7) -0.0026(6) 0.0015(6) 0.0034(6) C19 0.0288(8) 0.0292(8) 0.0231(7) 0.0003(6) -0.0006(6) 0.0041(6) N1 0.0254(6) 0.0258(7) 0.0253(6) 0.0046(5) 0.0042(5) 0.0012(5) N2 0.0413(8) 0.0300(8) 0.0342(7) -0.0024(6) 0.0028(6) -0.0006(6) N3 0.0386(8) 0.0535(10) 0.0263(7) 0.0044(6) 0.0066(6) 0.0049(7) O1 0.0251(5) 0.0216(5) 0.0261(5) -0.0038(4) 0.0002(4) 0.0050(4) O2 0.0283(6) 0.0234(5) 0.0267(5) -0.0043(4) -0.0028(4) 0.0057(4) O3 0.0258(6) 0.0383(7) 0.0321(6) 0.0043(5) 0.0096(5) 0.0017(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O2 1.4381(17) . ? C1 O1 1.4400(17) . ? C1 C11 1.492(2) . ? C1 H1 1 . ? C2 O2 1.4149(17) . ? C2 C9 1.491(2) . ? C2 C4 1.559(2) . ? C2 C3 1.5874(19) . ? C3 O1 1.4004(17) . ? C3 C18 1.478(2) . ? C3 C19 1.493(2) . ? C4 O3 1.2145(18) . ? C4 N1 1.3590(19) . ? C5 C9 1.380(2) . ? C5 C6 1.392(2) . ? C5 H5 0.95 . ? C6 C7 1.382(2) . ? C6 H6 0.95 . ? C7 C8 1.392(2) . ? C7 H7 0.95 . ? C8 C10 1.376(2) . ? C8 H8 0.95 . ? C9 C10 1.392(2) . ? C10 N1 1.4120(19) . ? C11 C12 1.388(2) . ? C11 C16 1.396(2) . ? C12 C13 1.373(2) . ? C12 H12 0.95 . ? C13 C14 1.383(2) . ? C13 H13 0.95 . ? C14 C15 1.379(2) . ? C14 H14 0.95 . ? C15 C16 1.392(2) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 N1 1.455(2) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? C17 H17D 0.98 . ? C17 H17E 0.98 . ? C17 H17F 0.98 . ? C18 N2 1.144(2) . ? C19 N3 1.145(2) . ? 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 O2 C1 O1 104.46(11) . . ? O2 C1 C11 111.29(12) . . ? O1 C1 C11 109.36(12) . . ? O2 C1 H1 110.5 . . ? O1 C1 H1 110.5 . . ? C11 C1 H1 110.5 . . ? O2 C2 C9 115.42(12) . . ? O2 C2 C4 111.41(12) . . ? C9 C2 C4 102.62(11) . . ? O2 C2 C3 102.08(10) . . ? C9 C2 C3 116.67(12) . . ? C4 C2 C3 108.76(11) . . ? O1 C3 C18 110.03(12) . . ? O1 C3 C19 111.03(12) . . ? C18 C3 C19 107.86(12) . . ? O1 C3 C2 103.32(11) . . ? C18 C3 C2 112.55(12) . . ? C19 C3 C2 112.06(12) . . ? O3 C4 N1 127.40(14) . . ? O3 C4 C2 125.45(13) . . ? N1 C4 C2 107.09(12) . . ? C9 C5 C6 118.55(15) . . ? C9 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C7 C6 C5 120.24(15) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 121.87(14) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C10 C8 C7 117.00(14) . . ? C10 C8 H8 121.5 . . ? C7 C8 H8 121.5 . . ? C5 C9 C10 120.25(14) . . ? C5 C9 C2 131.20(14) . . ? C10 C9 C2 108.54(13) . . ? C8 C10 C9 122.08(14) . . ? C8 C10 N1 127.93(14) . . ? C9 C10 N1 109.94(12) . . ? C12 C11 C16 120.23(14) . . ? C12 C11 C1 119.97(14) . . ? C16 C11 C1 119.78(14) . . ? C13 C12 C11 119.99(15) . . ? C13 C12 H12 120 . . ? C11 C12 H12 120 . . ? C12 C13 C14 119.87(15) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 121.02(15) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 119.49(15) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C15 C16 C11 119.38(15) . . ? C15 C16 H16 120.3 . . ? C11 C16 H16 120.3 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? N1 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? N1 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? N2 C18 C3 175.70(16) . . ? N3 C19 C3 178.89(16) . . ? C4 N1 C10 111.30(12) . . ? C4 N1 C17 124.01(13) . . ? C10 N1 C17 124.69(13) . . ? C3 O1 C1 106.11(10) . . ? C2 O2 C1 110.88(10) . . ? 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 O2 C2 C3 O1 23.33(14) . . . . ? C9 C2 C3 O1 150.10(12) . . . . ? C4 C2 C3 O1 -94.51(13) . . . . ? O2 C2 C3 C18 141.97(12) . . . . ? C9 C2 C3 C18 -91.25(16) . . . . ? C4 C2 C3 C18 24.13(16) . . . . ? O2 C2 C3 C19 -96.26(13) . . . . ? C9 C2 C3 C19 30.52(18) . . . . ? C4 C2 C3 C19 145.90(12) . . . . ? O2 C2 C4 O3 -51.36(19) . . . . ? C9 C2 C4 O3 -175.43(14) . . . . ? C3 C2 C4 O3 60.39(19) . . . . ? O2 C2 C4 N1 131.19(12) . . . . ? C9 C2 C4 N1 7.12(15) . . . . ? C3 C2 C4 N1 -117.06(12) . . . . ? C9 C5 C6 C7 0.6(2) . . . . ? C5 C6 C7 C8 0.5(2) . . . . ? C6 C7 C8 C10 -0.8(2) . . . . ? C6 C5 C9 C10 -1.3(2) . . . . ? C6 C5 C9 C2 179.85(14) . . . . ? O2 C2 C9 C5 51.8(2) . . . . ? C4 C2 C9 C5 173.21(15) . . . . ? C3 C2 C9 C5 -68.0(2) . . . . ? O2 C2 C9 C10 -127.08(13) . . . . ? C4 C2 C9 C10 -5.70(15) . . . . ? C3 C2 C9 C10 113.06(14) . . . . ? C7 C8 C10 C9 0.0(2) . . . . ? C7 C8 C10 N1 177.17(14) . . . . ? C5 C9 C10 C8 1.1(2) . . . . ? C2 C9 C10 C8 -179.86(13) . . . . ? C5 C9 C10 N1 -176.56(13) . . . . ? C2 C9 C10 N1 2.50(16) . . . . ? O2 C1 C11 C12 61.08(17) . . . . ? O1 C1 C11 C12 -53.81(17) . . . . ? O2 C1 C11 C16 -120.27(14) . . . . ? O1 C1 C11 C16 124.84(14) . . . . ? C16 C11 C12 C13 -1.5(2) . . . . ? C1 C11 C12 C13 177.19(13) . . . . ? C11 C12 C13 C14 0.5(2) . . . . ? C12 C13 C14 C15 0.9(2) . . . . ? C13 C14 C15 C16 -1.2(2) . . . . ? C14 C15 C16 C11 0.3(2) . . . . ? C12 C11 C16 C15 1.1(2) . . . . ? C1 C11 C16 C15 -177.58(13) . . . . ? O1 C3 C18 N2 166(2) . . . . ? C19 C3 C18 N2 -73(2) . . . . ? C2 C3 C18 N2 51(2) . . . . ? O1 C3 C19 N3 62(9) . . . . ? C18 C3 C19 N3 -59(9) . . . . ? C2 C3 C19 N3 18E1(10) . . . . ? O3 C4 N1 C10 176.54(15) . . . . ? C2 C4 N1 C10 -6.08(16) . . . . ? O3 C4 N1 C17 -3.4(2) . . . . ? C2 C4 N1 C17 174.00(13) . . . . ? C8 C10 N1 C4 -175.00(14) . . . . ? C9 C10 N1 C4 2.47(17) . . . . ? C8 C10 N1 C17 4.9(2) . . . . ? C9 C10 N1 C17 -177.61(14) . . . . ? C18 C3 O1 C1 -156.11(12) . . . . ? C19 C3 O1 C1 84.56(13) . . . . ? C2 C3 O1 C1 -35.73(13) . . . . ? O2 C1 O1 C3 34.90(14) . . . . ? C11 C1 O1 C3 154.11(11) . . . . ? C9 C2 O2 C1 -129.89(13) . . . . ? C4 C2 O2 C1 113.62(13) . . . . ? C3 C2 O2 C1 -2.31(15) . . . . ? O1 C1 O2 C2 -18.97(15) . . . . ? C11 C1 O2 C2 -136.87(13) . . . . ? data_7b _database_code_depnum_ccdc_archive 'CCDC 654058' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H12 Cl1 N3 O3' _chemical_formula_sum 'C19 H12 Cl N3 O3' _chemical_formula_weight 365.77 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1044(8) _cell_length_b 9.8097(8) _cell_length_c 10.3197(9) _cell_angle_alpha 76.326(5) _cell_angle_beta 69.235(4) _cell_angle_gamma 87.179(4) _cell_volume 836.76(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4879 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.47 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.32 _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.253 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_T_max 0.922 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_unetI/netI 0.0355 _diffrn_reflns_number 11773 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 3795 _reflns_number_gt 3188 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0694P)^2^+0.2316P] 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_number_reflns 3795 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.424 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.78680(17) 0.33098(17) 0.00998(16) 0.0206(3) Uani 1 d . . . H1 H 0.8408 0.4188 0.0065 0.025 Uiso 1 calc R . . C2 C 0.52848(16) 0.33251(15) 0.15513(15) 0.0168(3) Uani 1 d . . . C3 C 0.60607(16) 0.19894(16) 0.22042(16) 0.0178(3) Uani 1 d . . . C4 C 0.53131(18) 0.44992(16) 0.23317(16) 0.0197(3) Uani 1 d . . . C5 C 0.27992(17) 0.24117(16) 0.12223(16) 0.0193(3) Uani 1 d . . . H5 H 0.3364 0.1889 0.0546 0.023 Uiso 1 calc R . . C6 C 0.11527(18) 0.24428(17) 0.16870(18) 0.0230(3) Uani 1 d . . . H6 H 0.0592 0.1934 0.1322 0.028 Uiso 1 calc R . . C7 C 0.03343(18) 0.32085(18) 0.26740(18) 0.0254(4) Uani 1 d . . . H7 H -0.0781 0.3203 0.2983 0.03 Uiso 1 calc R . . C8 C 0.11162(18) 0.39906(17) 0.32254(17) 0.0233(3) Uani 1 d . . . H8 H 0.0555 0.452 0.3896 0.028 Uiso 1 calc R . . C9 C 0.35748(16) 0.31646(15) 0.17787(16) 0.0167(3) Uani 1 d . . . C10 C 0.27383(17) 0.39590(16) 0.27522(16) 0.0181(3) Uani 1 d . . . C11 C 0.88071(17) 0.27001(16) -0.11419(16) 0.0202(3) Uani 1 d . . . C12 C 0.80785(18) 0.18461(17) -0.16646(17) 0.0222(3) Uani 1 d . . . H12 H 0.6969 0.1696 -0.1279 0.027 Uiso 1 calc R . . C13 C 0.89799(18) 0.12161(17) -0.27499(17) 0.0228(3) Uani 1 d . . . H13 H 0.8492 0.0646 -0.3121 0.027 Uiso 1 calc R . . C14 C 1.06077(18) 0.14330(17) -0.32854(17) 0.0220(3) Uani 1 d . . . C15 C 1.13513(18) 0.22822(17) -0.27875(17) 0.0235(3) Uani 1 d . . . H15 H 1.2462 0.2421 -0.3168 0.028 Uiso 1 calc R . . C16 C 1.04361(18) 0.29285(17) -0.17172(17) 0.0223(3) Uani 1 d . . . H16 H 1.0925 0.3529 -0.1377 0.027 Uiso 1 calc R . . C17 C 0.3334(2) 0.56513(18) 0.40595(19) 0.0275(4) Uani 1 d . . . H17A H 0.2185 0.5641 0.4485 0.041 Uiso 0.5 calc PR . . H17B H 0.3734 0.6608 0.3532 0.041 Uiso 0.5 calc PR . . H17C H 0.3775 0.5335 0.4815 0.041 Uiso 0.5 calc PR . . H17D H 0.4278 0.6081 0.407 0.041 Uiso 0.5 calc PR . . H17E H 0.2729 0.5115 0.5022 0.041 Uiso 0.5 calc PR . . H17F H 0.2688 0.6388 0.374 0.041 Uiso 0.5 calc PR . . C18 C 0.57329(17) 0.18443(16) 0.37478(16) 0.0193(3) Uani 1 d . . . C19 C 0.55526(17) 0.06815(16) 0.19498(16) 0.0193(3) Uani 1 d . . . N1 N 0.37925(15) 0.47136(14) 0.30870(14) 0.0196(3) Uani 1 d . . . N2 N 0.54438(16) 0.18005(15) 0.49265(15) 0.0261(3) Uani 1 d . . . N3 N 0.52253(17) -0.03042(15) 0.16850(16) 0.0270(3) Uani 1 d . . . O1 O 0.76825(12) 0.22752(12) 0.14397(11) 0.0219(3) Uani 1 d . . . O2 O 0.63157(12) 0.35939(11) 0.01104(11) 0.0191(2) Uani 1 d . . . O3 O 0.64960(13) 0.50597(12) 0.23059(13) 0.0264(3) Uani 1 d . . . Cl3 Cl 1.17315(5) 0.05779(4) -0.45924(4) 0.02926(14) Uani 1 d . . . 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 C1 0.0129(7) 0.0244(8) 0.0227(8) -0.0054(6) -0.0033(6) -0.0052(6) C2 0.0132(7) 0.0191(7) 0.0169(7) -0.0040(6) -0.0034(5) -0.0033(5) C3 0.0106(6) 0.0229(8) 0.0200(7) -0.0063(6) -0.0047(5) -0.0006(5) C4 0.0180(7) 0.0198(8) 0.0207(7) -0.0043(6) -0.0060(6) -0.0024(6) C5 0.0169(7) 0.0187(7) 0.0227(8) -0.0039(6) -0.0081(6) -0.0001(6) C6 0.0183(7) 0.0241(8) 0.0296(9) -0.0046(7) -0.0129(6) -0.0018(6) C7 0.0136(7) 0.0319(9) 0.0313(9) -0.0070(7) -0.0091(6) 0.0022(6) C8 0.0174(7) 0.0273(9) 0.0253(8) -0.0081(7) -0.0069(6) 0.0046(6) C9 0.0133(7) 0.0172(7) 0.0185(7) -0.0016(6) -0.0055(5) -0.0015(5) C10 0.0168(7) 0.0183(7) 0.0203(7) -0.0039(6) -0.0082(6) -0.0006(6) C11 0.0160(7) 0.0214(8) 0.0212(8) -0.0047(6) -0.0038(6) -0.0036(6) C12 0.0149(7) 0.0242(8) 0.0252(8) -0.0055(6) -0.0036(6) -0.0058(6) C13 0.0191(7) 0.0230(8) 0.0258(8) -0.0063(6) -0.0065(6) -0.0041(6) C14 0.0196(7) 0.0216(8) 0.0215(8) -0.0049(6) -0.0033(6) 0.0018(6) C15 0.0130(7) 0.0278(9) 0.0263(8) -0.0053(7) -0.0032(6) -0.0027(6) C16 0.0166(7) 0.0246(8) 0.0240(8) -0.0048(6) -0.0050(6) -0.0045(6) C17 0.0278(9) 0.0286(9) 0.0327(9) -0.0169(7) -0.0128(7) 0.0050(7) C18 0.0133(7) 0.0209(8) 0.0239(8) -0.0053(6) -0.0068(6) 0.0009(6) C19 0.0153(7) 0.0223(8) 0.0202(7) -0.0040(6) -0.0068(6) 0.0014(6) N1 0.0168(6) 0.0210(7) 0.0230(7) -0.0086(5) -0.0071(5) 0.0002(5) N2 0.0252(7) 0.0282(8) 0.0248(8) -0.0076(6) -0.0074(6) -0.0004(6) N3 0.0289(7) 0.0243(7) 0.0304(8) -0.0065(6) -0.0134(6) -0.0001(6) O1 0.0102(5) 0.0326(6) 0.0215(6) -0.0056(5) -0.0043(4) -0.0016(4) O2 0.0130(5) 0.0232(6) 0.0182(5) -0.0041(4) -0.0019(4) -0.0028(4) O3 0.0199(6) 0.0281(6) 0.0330(7) -0.0108(5) -0.0079(5) -0.0086(5) Cl3 0.0210(2) 0.0321(2) 0.0324(2) -0.01492(18) -0.00206(16) 0.00259(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O2 1.4237(18) . ? C1 O1 1.4691(19) . ? C1 C11 1.505(2) . ? C1 H1 1 . ? C2 O2 1.4180(17) . ? C2 C9 1.5004(19) . ? C2 C4 1.559(2) . ? C2 C3 1.581(2) . ? C3 O1 1.4112(17) . ? C3 C18 1.486(2) . ? C3 C19 1.494(2) . ? C4 O3 1.2222(18) . ? C4 N1 1.3609(19) . ? C5 C9 1.383(2) . ? C5 C6 1.404(2) . ? C5 H5 0.95 . ? C6 C7 1.388(2) . ? C6 H6 0.95 . ? C7 C8 1.402(2) . ? C7 H7 0.95 . ? C8 C10 1.383(2) . ? C8 H8 0.95 . ? C9 C10 1.402(2) . ? C10 N1 1.4194(19) . ? C11 C16 1.396(2) . ? C11 C12 1.398(2) . ? C12 C13 1.391(2) . ? C12 H12 0.95 . ? C13 C14 1.393(2) . ? C13 H13 0.95 . ? C14 C15 1.386(2) . ? C14 Cl3 1.7441(15) . ? C15 C16 1.394(2) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 N1 1.4592(19) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? C17 H17D 0.98 . ? C17 H17E 0.98 . ? C17 H17F 0.98 . ? C18 N2 1.140(2) . ? C19 N3 1.144(2) . ? 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 O2 C1 O1 105.70(11) . . ? O2 C1 C11 111.24(12) . . ? O1 C1 C11 109.53(13) . . ? O2 C1 H1 110.1 . . ? O1 C1 H1 110.1 . . ? C11 C1 H1 110.1 . . ? O2 C2 C9 115.33(12) . . ? O2 C2 C4 114.48(12) . . ? C9 C2 C4 103.08(11) . . ? O2 C2 C3 99.80(11) . . ? C9 C2 C3 116.31(12) . . ? C4 C2 C3 108.15(11) . . ? O1 C3 C18 109.57(12) . . ? O1 C3 C19 110.01(12) . . ? C18 C3 C19 110.66(13) . . ? O1 C3 C2 103.03(12) . . ? C18 C3 C2 111.87(12) . . ? C19 C3 C2 111.44(12) . . ? O3 C4 N1 127.46(14) . . ? O3 C4 C2 125.47(14) . . ? N1 C4 C2 106.99(12) . . ? C9 C5 C6 117.99(14) . . ? C9 C5 H5 121 . . ? C6 C5 H5 121 . . ? C7 C6 C5 120.76(14) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 121.48(14) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C10 C8 C7 117.20(14) . . ? C10 C8 H8 121.4 . . ? C7 C8 H8 121.4 . . ? C5 C9 C10 120.75(13) . . ? C5 C9 C2 131.74(13) . . ? C10 C9 C2 107.51(12) . . ? C8 C10 C9 121.78(14) . . ? C8 C10 N1 127.88(14) . . ? C9 C10 N1 110.29(12) . . ? C16 C11 C12 119.97(14) . . ? C16 C11 C1 119.14(13) . . ? C12 C11 C1 120.79(13) . . ? C13 C12 C11 119.94(14) . . ? C13 C12 H12 120 . . ? C11 C12 H12 120 . . ? C12 C13 C14 119.08(14) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C15 C14 C13 121.84(14) . . ? C15 C14 Cl3 119.49(12) . . ? C13 C14 Cl3 118.65(12) . . ? C14 C15 C16 118.65(14) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C15 C16 C11 120.48(14) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? N1 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? N1 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? N2 C18 C3 176.33(16) . . ? N3 C19 C3 176.35(16) . . ? C4 N1 C10 111.09(12) . . ? C4 N1 C17 123.57(13) . . ? C10 N1 C17 125.29(13) . . ? C3 O1 C1 108.24(11) . . ? C2 O2 C1 107.98(11) . . ? 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 O2 C2 C3 O1 36.06(13) . . . . ? C9 C2 C3 O1 160.80(12) . . . . ? C4 C2 C3 O1 -83.88(13) . . . . ? O2 C2 C3 C18 153.67(11) . . . . ? C9 C2 C3 C18 -81.60(15) . . . . ? C4 C2 C3 C18 33.73(16) . . . . ? O2 C2 C3 C19 -81.85(13) . . . . ? C9 C2 C3 C19 42.88(16) . . . . ? C4 C2 C3 C19 158.21(12) . . . . ? O2 C2 C4 O3 -46.8(2) . . . . ? C9 C2 C4 O3 -172.82(15) . . . . ? C3 C2 C4 O3 63.47(19) . . . . ? O2 C2 C4 N1 136.26(13) . . . . ? C9 C2 C4 N1 10.22(15) . . . . ? C3 C2 C4 N1 -113.49(13) . . . . ? C9 C5 C6 C7 0.1(2) . . . . ? C5 C6 C7 C8 0.9(3) . . . . ? C6 C7 C8 C10 -0.5(2) . . . . ? C6 C5 C9 C10 -1.4(2) . . . . ? C6 C5 C9 C2 178.09(15) . . . . ? O2 C2 C9 C5 46.1(2) . . . . ? C4 C2 C9 C5 171.63(16) . . . . ? C3 C2 C9 C5 -70.2(2) . . . . ? O2 C2 C9 C10 -134.28(13) . . . . ? C4 C2 C9 C10 -8.79(15) . . . . ? C3 C2 C9 C10 109.35(14) . . . . ? C7 C8 C10 C9 -0.9(2) . . . . ? C7 C8 C10 N1 176.29(15) . . . . ? C5 C9 C10 C8 1.9(2) . . . . ? C2 C9 C10 C8 -177.70(14) . . . . ? C5 C9 C10 N1 -175.73(13) . . . . ? C2 C9 C10 N1 4.62(17) . . . . ? O2 C1 C11 C16 151.39(14) . . . . ? O1 C1 C11 C16 -92.13(17) . . . . ? O2 C1 C11 C12 -32.4(2) . . . . ? O1 C1 C11 C12 84.12(17) . . . . ? C16 C11 C12 C13 0.5(2) . . . . ? C1 C11 C12 C13 -175.70(15) . . . . ? C11 C12 C13 C14 1.0(2) . . . . ? C12 C13 C14 C15 -1.4(3) . . . . ? C12 C13 C14 Cl3 177.31(13) . . . . ? C13 C14 C15 C16 0.3(2) . . . . ? Cl3 C14 C15 C16 -178.40(12) . . . . ? C14 C15 C16 C11 1.3(2) . . . . ? C12 C11 C16 C15 -1.6(2) . . . . ? C1 C11 C16 C15 174.64(15) . . . . ? O1 C3 C18 N2 108(2) . . . . ? C19 C3 C18 N2 -130(2) . . . . ? C2 C3 C18 N2 -6(3) . . . . ? O1 C3 C19 N3 -29(3) . . . . ? C18 C3 C19 N3 -151(2) . . . . ? C2 C3 C19 N3 84(2) . . . . ? O3 C4 N1 C10 175.12(16) . . . . ? C2 C4 N1 C10 -7.99(17) . . . . ? O3 C4 N1 C17 -2.3(3) . . . . ? C2 C4 N1 C17 174.56(14) . . . . ? C8 C10 N1 C4 -175.13(15) . . . . ? C9 C10 N1 C4 2.36(18) . . . . ? C8 C10 N1 C17 2.3(3) . . . . ? C9 C10 N1 C17 179.75(14) . . . . ? C18 C3 O1 C1 -140.85(12) . . . . ? C19 C3 O1 C1 97.29(14) . . . . ? C2 C3 O1 C1 -21.63(14) . . . . ? O2 C1 O1 C3 -0.69(15) . . . . ? C11 C1 O1 C3 -120.62(13) . . . . ? C9 C2 O2 C1 -163.17(12) . . . . ? C4 C2 O2 C1 77.45(14) . . . . ? C3 C2 O2 C1 -37.77(13) . . . . ? O1 C1 O2 C2 26.09(14) . . . . ? C11 C1 O2 C2 144.89(12) . . . . ? #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-06-11 at 14:14:48 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\progs\wingx\files\archive.dat # CIF files read : job struct data_7a _database_code_depnum_ccdc_archive 'CCDC 654059' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H12 Cl1 N3 O3' _chemical_formula_sum 'C19 H12 Cl N3 O3' _chemical_formula_weight 365.77 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.887(2) _cell_length_b 6.6306(8) _cell_length_c 23.230(2) _cell_angle_alpha 90 _cell_angle_beta 90.527(5) _cell_angle_gamma 90 _cell_volume 3371.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6199 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.36 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.24 _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.252 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.808 _exptl_absorpt_correction_T_max 0.941 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_unetI/netI 0.0481 _diffrn_reflns_number 15026 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 3840 _reflns_number_gt 3284 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0467P)^2^+4.8133P] 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_number_reflns 3840 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.494 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.35129(7) 0.0192(3) 0.53465(7) 0.0195(3) Uani 1 d . . . H1 H 0.3268 -0.1055 0.5418 0.023 Uiso 1 calc R . . C2 C 0.34755(7) 0.2167(3) 0.61741(7) 0.0180(3) Uani 1 d . . . C3 C 0.29070(7) 0.2558(3) 0.57572(6) 0.0164(3) Uani 1 d . . . C4 C 0.38549(8) 0.4145(3) 0.62538(8) 0.0271(4) Uani 1 d . . . C5 C 0.30611(8) -0.0149(4) 0.69980(8) 0.0311(5) Uani 1 d . . . H5 H 0.291 -0.1179 0.6751 0.037 Uiso 1 calc R . . C6 C 0.30130(9) -0.0309(5) 0.76008(9) 0.0502(7) Uani 1 d . . . H6 H 0.2825 -0.1461 0.7766 0.06 Uiso 1 calc R . . C7 C 0.32387(9) 0.1207(6) 0.79542(8) 0.0602(9) Uani 1 d . . . H7 H 0.3201 0.1071 0.8359 0.072 Uiso 1 calc R . . C8 C 0.35168(9) 0.2912(5) 0.77349(8) 0.0491(7) Uani 1 d . . . H8 H 0.367 0.3941 0.7982 0.059 Uiso 1 calc R . . C9 C 0.33350(7) 0.1554(3) 0.67804(7) 0.0212(4) Uani 1 d . . . C10 C 0.35640(8) 0.3064(4) 0.71460(8) 0.0299(5) Uani 1 d . . . C11 C 0.39376(7) -0.0136(3) 0.48532(7) 0.0185(3) Uani 1 d . . . C12 C 0.39444(7) -0.2010(3) 0.45860(7) 0.0211(4) Uani 1 d . . . H12 H 0.3703 -0.3079 0.4734 0.025 Uiso 1 calc R . . C13 C 0.43027(7) -0.2327(3) 0.41027(7) 0.0220(4) Uani 1 d . . . H13 H 0.4313 -0.3608 0.392 0.026 Uiso 1 calc R . . C14 C 0.46440(7) -0.0733(3) 0.38946(7) 0.0209(4) Uani 1 d . . . C15 C 0.46671(8) 0.1126(3) 0.41699(8) 0.0249(4) Uani 1 d . . . H15 H 0.4922 0.2174 0.403 0.03 Uiso 1 calc R . . C16 C 0.43096(8) 0.1420(3) 0.46542(7) 0.0235(4) Uani 1 d . . . H16 H 0.4318 0.2679 0.485 0.028 Uiso 1 calc R . . C17 C 0.42103(11) 0.6265(4) 0.70579(15) 0.0624(9) Uani 1 d . . . H17A H 0.4141 0.6383 0.7473 0.094 Uiso 0.5 calc PR . . H17B H 0.4095 0.753 0.6868 0.094 Uiso 0.5 calc PR . . H17C H 0.4644 0.5989 0.699 0.094 Uiso 0.5 calc PR . . H17D H 0.4445 0.6885 0.6747 0.094 Uiso 0.5 calc PR . . H17E H 0.4491 0.5738 0.7352 0.094 Uiso 0.5 calc PR . . H17F H 0.3942 0.7279 0.723 0.094 Uiso 0.5 calc PR . . C18 C 0.27422(7) 0.4723(3) 0.57124(7) 0.0193(3) Uani 1 d . . . C19 C 0.23421(7) 0.1484(3) 0.59494(7) 0.0180(3) Uani 1 d . . . N1 N 0.38402(7) 0.4613(3) 0.68243(8) 0.0332(4) Uani 1 d . . . N2 N 0.25982(7) 0.6381(3) 0.57103(7) 0.0285(4) Uani 1 d . . . N3 N 0.18975(7) 0.0746(3) 0.60972(6) 0.0251(3) Uani 1 d . . . O1 O 0.31118(5) 0.18732(19) 0.52200(5) 0.0193(3) Uani 1 d . . . O2 O 0.38289(5) 0.0780(2) 0.58568(5) 0.0243(3) Uani 1 d . . . O3 O 0.41057(6) 0.5061(3) 0.58710(7) 0.0418(4) Uani 1 d . . . Cl1 Cl 0.503868(18) -0.10638(8) 0.324971(17) 0.02829(14) Uani 1 d . . . 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 C1 0.0211(8) 0.0174(9) 0.0201(8) -0.0014(6) 0.0023(6) 0.0006(6) C2 0.0154(7) 0.0205(9) 0.0182(7) -0.0018(7) 0.0009(6) -0.0004(6) C3 0.0168(7) 0.0178(9) 0.0147(7) -0.0023(6) 0.0019(6) -0.0011(6) C4 0.0188(8) 0.0247(10) 0.0378(10) -0.0015(8) -0.0059(7) -0.0015(7) C5 0.0194(8) 0.0486(14) 0.0252(9) 0.0117(9) -0.0012(7) -0.0013(8) C6 0.0207(9) 0.100(2) 0.0300(10) 0.0308(13) 0.0017(8) -0.0017(11) C7 0.0204(9) 0.145(3) 0.0150(9) 0.0044(13) 0.0001(7) 0.0059(13) C8 0.0200(9) 0.105(2) 0.0219(9) -0.0255(12) -0.0019(7) 0.0115(11) C9 0.0159(7) 0.0337(11) 0.0141(7) -0.0016(7) 0.0010(6) 0.0023(7) C10 0.0146(7) 0.0507(14) 0.0244(9) -0.0152(9) -0.0019(6) 0.0082(8) C11 0.0166(7) 0.0226(9) 0.0164(7) -0.0011(7) 0.0008(6) 0.0009(6) C12 0.0209(8) 0.0213(10) 0.0210(8) -0.0012(7) 0.0003(6) -0.0015(7) C13 0.0218(8) 0.0226(10) 0.0217(8) -0.0062(7) -0.0013(6) 0.0018(7) C14 0.0150(7) 0.0326(11) 0.0151(7) -0.0039(7) 0.0020(6) 0.0035(7) C15 0.0238(8) 0.0258(10) 0.0252(8) -0.0005(7) 0.0055(7) -0.0029(7) C16 0.0245(8) 0.0219(10) 0.0241(8) -0.0044(7) 0.0042(7) -0.0012(7) C17 0.0324(12) 0.0535(17) 0.101(2) -0.0482(16) -0.0205(13) -0.0006(11) C18 0.0184(7) 0.0197(10) 0.0197(8) 0.0005(7) 0.0018(6) -0.0031(6) C19 0.0194(8) 0.0172(9) 0.0172(7) -0.0008(6) -0.0011(6) 0.0005(6) N1 0.0221(7) 0.0303(10) 0.0472(10) -0.0199(8) -0.0084(7) 0.0015(7) N2 0.0261(8) 0.0204(9) 0.0389(9) 0.0019(7) 0.0028(6) -0.0023(6) N3 0.0218(7) 0.0269(9) 0.0266(7) 0.0040(6) -0.0005(6) -0.0033(6) O1 0.0187(5) 0.0242(7) 0.0151(5) -0.0039(5) 0.0016(4) 0.0036(5) O2 0.0241(6) 0.0340(8) 0.0147(5) -0.0048(5) 0.0000(4) 0.0106(5) O3 0.0318(7) 0.0377(10) 0.0558(9) 0.0145(8) -0.0060(7) -0.0157(7) Cl1 0.0220(2) 0.0443(3) 0.0186(2) -0.00859(18) 0.00543(15) 0.00050(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O2 1.4216(19) . ? C1 O1 1.448(2) . ? C1 C11 1.498(2) . ? C1 H1 1 . ? C2 O2 1.413(2) . ? C2 C9 1.501(2) . ? C2 C4 1.563(3) . ? C2 C3 1.591(2) . ? C3 O1 1.4051(18) . ? C3 C18 1.484(3) . ? C3 C19 1.498(2) . ? C4 O3 1.212(2) . ? C4 N1 1.362(3) . ? C5 C9 1.376(3) . ? C5 C6 1.409(3) . ? C5 H5 0.95 . ? C6 C7 1.386(4) . ? C6 H6 0.95 . ? C7 C8 1.383(4) . ? C7 H7 0.95 . ? C8 C10 1.377(3) . ? C8 H8 0.95 . ? C9 C10 1.402(3) . ? C10 N1 1.410(3) . ? C11 C12 1.389(3) . ? C11 C16 1.396(2) . ? C12 C13 1.392(2) . ? C12 H12 0.95 . ? C13 C14 1.384(3) . ? C13 H13 0.95 . ? C14 C15 1.390(3) . ? C14 Cl1 1.7499(16) . ? C15 C16 1.390(2) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 N1 1.464(3) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? C17 H17D 0.98 . ? C17 H17E 0.98 . ? C17 H17F 0.98 . ? C18 N2 1.144(2) . ? C19 N3 1.145(2) . ? 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 O2 C1 O1 104.32(13) . . ? O2 C1 C11 112.16(13) . . ? O1 C1 C11 109.63(13) . . ? O2 C1 H1 110.2 . . ? O1 C1 H1 110.2 . . ? C11 C1 H1 110.2 . . ? O2 C2 C9 115.55(15) . . ? O2 C2 C4 108.36(13) . . ? C9 C2 C4 103.26(14) . . ? O2 C2 C3 102.55(12) . . ? C9 C2 C3 116.71(13) . . ? C4 C2 C3 110.32(14) . . ? O1 C3 C18 109.25(13) . . ? O1 C3 C19 112.47(13) . . ? C18 C3 C19 106.25(13) . . ? O1 C3 C2 103.52(12) . . ? C18 C3 C2 112.87(13) . . ? C19 C3 C2 112.59(13) . . ? O3 C4 N1 127.92(19) . . ? O3 C4 C2 125.27(18) . . ? N1 C4 C2 106.82(16) . . ? C9 C5 C6 117.6(2) . . ? C9 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? C7 C6 C5 120.3(2) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 122.02(19) . . ? C8 C7 H7 119 . . ? C6 C7 H7 119 . . ? C10 C8 C7 117.6(2) . . ? C10 C8 H8 121.2 . . ? C7 C8 H8 121.2 . . ? C5 C9 C10 121.17(17) . . ? C5 C9 C2 131.34(17) . . ? C10 C9 C2 107.44(16) . . ? C8 C10 C9 121.3(2) . . ? C8 C10 N1 128.1(2) . . ? C9 C10 N1 110.60(16) . . ? C12 C11 C16 120.30(15) . . ? C12 C11 C1 118.75(15) . . ? C16 C11 C1 120.93(16) . . ? C11 C12 C13 120.29(16) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 118.45(17) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C13 C14 C15 122.29(15) . . ? C13 C14 Cl1 118.41(14) . . ? C15 C14 Cl1 119.27(14) . . ? C14 C15 C16 118.60(17) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C15 C16 C11 119.92(17) . . ? C15 C16 H16 120 . . ? C11 C16 H16 120 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? N1 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? N1 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? N2 C18 C3 175.76(18) . . ? N3 C19 C3 176.93(18) . . ? C4 N1 C10 111.35(16) . . ? C4 N1 C17 120.9(2) . . ? C10 N1 C17 126.0(2) . . ? C3 O1 C1 105.45(12) . . ? C2 O2 C1 110.43(12) . . ? 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 O2 C2 C3 O1 -17.58(16) . . . . ? C9 C2 C3 O1 -144.93(15) . . . . ? C4 C2 C3 O1 97.67(15) . . . . ? O2 C2 C3 C18 -135.57(14) . . . . ? C9 C2 C3 C18 97.08(18) . . . . ? C4 C2 C3 C18 -20.32(18) . . . . ? O2 C2 C3 C19 104.14(15) . . . . ? C9 C2 C3 C19 -23.2(2) . . . . ? C4 C2 C3 C19 -140.61(14) . . . . ? O2 C2 C4 O3 50.6(2) . . . . ? C9 C2 C4 O3 173.61(18) . . . . ? C3 C2 C4 O3 -61.0(2) . . . . ? O2 C2 C4 N1 -129.89(15) . . . . ? C9 C2 C4 N1 -6.86(18) . . . . ? C3 C2 C4 N1 118.57(15) . . . . ? C9 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 -0.1(4) . . . . ? C6 C7 C8 C10 0.0(3) . . . . ? C6 C5 C9 C10 0.7(3) . . . . ? C6 C5 C9 C2 177.85(18) . . . . ? O2 C2 C9 C5 -55.4(2) . . . . ? C4 C2 C9 C5 -173.55(18) . . . . ? C3 C2 C9 C5 65.3(3) . . . . ? O2 C2 C9 C10 122.04(16) . . . . ? C4 C2 C9 C10 3.91(18) . . . . ? C3 C2 C9 C10 -117.28(16) . . . . ? C7 C8 C10 C9 0.4(3) . . . . ? C7 C8 C10 N1 -178.13(19) . . . . ? C5 C9 C10 C8 -0.8(3) . . . . ? C2 C9 C10 C8 -178.58(17) . . . . ? C5 C9 C10 N1 177.99(16) . . . . ? C2 C9 C10 N1 0.22(19) . . . . ? O2 C1 C11 C12 121.95(16) . . . . ? O1 C1 C11 C12 -122.66(16) . . . . ? O2 C1 C11 C16 -59.6(2) . . . . ? O1 C1 C11 C16 55.7(2) . . . . ? C16 C11 C12 C13 -2.7(2) . . . . ? C1 C11 C12 C13 175.69(15) . . . . ? C11 C12 C13 C14 -0.6(2) . . . . ? C12 C13 C14 C15 3.7(3) . . . . ? C12 C13 C14 Cl1 -174.20(12) . . . . ? C13 C14 C15 C16 -3.4(3) . . . . ? Cl1 C14 C15 C16 174.51(13) . . . . ? C14 C15 C16 C11 -0.1(3) . . . . ? C12 C11 C16 C15 3.1(3) . . . . ? C1 C11 C16 C15 -175.33(16) . . . . ? O1 C3 C18 N2 168(2) . . . . ? C19 C3 C18 N2 46(3) . . . . ? C2 C3 C18 N2 -78(2) . . . . ? O1 C3 C19 N3 -121(3) . . . . ? C18 C3 C19 N3 -2(3) . . . . ? C2 C3 C19 N3 122(3) . . . . ? O3 C4 N1 C10 -173.08(19) . . . . ? C2 C4 N1 C10 7.41(19) . . . . ? O3 C4 N1 C17 -7.5(3) . . . . ? C2 C4 N1 C17 172.99(18) . . . . ? C8 C10 N1 C4 173.62(19) . . . . ? C9 C10 N1 C4 -5.1(2) . . . . ? C8 C10 N1 C17 8.9(3) . . . . ? C9 C10 N1 C17 -169.78(18) . . . . ? C18 C3 O1 C1 154.06(13) . . . . ? C19 C3 O1 C1 -88.22(15) . . . . ? C2 C3 O1 C1 33.57(15) . . . . ? O2 C1 O1 C3 -37.76(15) . . . . ? C11 C1 O1 C3 -158.04(13) . . . . ? C9 C2 O2 C1 122.59(15) . . . . ? C4 C2 O2 C1 -122.15(15) . . . . ? C3 C2 O2 C1 -5.50(17) . . . . ? O1 C1 O2 C2 26.11(17) . . . . ? C11 C1 O2 C2 144.68(15) . . . . ? #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-06-11 at 14:14:48 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\progs\wingx\files\archive.dat # CIF files read : job struct data_15b _database_code_depnum_ccdc_archive 'CCDC 654060' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H15 N3 O4' _chemical_formula_sum 'C20 H15 N3 O4' _chemical_formula_weight 361.35 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0017(12) _cell_length_b 9.2015(12) _cell_length_c 11.8723(16) _cell_angle_alpha 84.823(7) _cell_angle_beta 69.598(7) _cell_angle_gamma 70.128(6) _cell_volume 866.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6282 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.19 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.925 _exptl_absorpt_correction_T_max 0.971 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_unetI/netI 0.0471 _diffrn_reflns_number 15218 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 3934 _reflns_number_gt 3213 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0685P)^2^+0.3911P] 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_number_reflns 3934 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.13 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.651 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.062 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4124(2) -0.07811(18) 0.31927(14) 0.0173(3) Uani 1 d . . . H1 H 0.4272 -0.0529 0.394 0.021 Uiso 1 calc R . . C2 C 0.1491(2) 0.08306(17) 0.32776(14) 0.0154(3) Uani 1 d . . . C3 C 0.28357(19) 0.12070(18) 0.21265(14) 0.0160(3) Uani 1 d . . . C4 C 0.1049(2) 0.19765(18) 0.43312(14) 0.0167(3) Uani 1 d . . . C5 C -0.0668(2) 0.02094(19) 0.25365(14) 0.0186(3) Uani 1 d . . . H5 H 0.0137 -0.0628 0.2009 0.022 Uiso 1 calc R . . C6 C -0.2357(2) 0.0673(2) 0.26482(15) 0.0210(4) Uani 1 d . . . H6 H -0.2708 0.0155 0.2183 0.025 Uiso 1 calc R . . C7 C -0.3536(2) 0.1886(2) 0.34349(15) 0.0219(4) Uani 1 d . . . H7 H -0.468 0.219 0.3493 0.026 Uiso 1 calc R . . C8 C -0.3068(2) 0.26694(19) 0.41430(15) 0.0202(3) Uani 1 d . . . H8 H -0.3874 0.3492 0.4685 0.024 Uiso 1 calc R . . C9 C -0.0188(2) 0.09990(18) 0.32134(14) 0.0157(3) Uani 1 d . . . C10 C -0.1391(2) 0.21962(18) 0.40205(14) 0.0164(3) Uani 1 d . . . C11 C 0.5358(2) -0.23261(18) 0.26779(14) 0.0177(3) Uani 1 d . . . C12 C 0.5193(2) -0.31009(19) 0.17977(15) 0.0215(4) Uani 1 d . . . H12 H 0.4219 -0.2694 0.1573 0.026 Uiso 1 calc R . . C13 C 0.6432(2) -0.44611(19) 0.12416(15) 0.0225(4) Uani 1 d . . . H13 H 0.6301 -0.4985 0.0647 0.027 Uiso 1 calc R . . C14 C 0.7871(2) -0.50497(18) 0.15660(15) 0.0206(4) Uani 1 d . . . C15 C 0.8028(2) -0.42933(19) 0.24647(15) 0.0212(4) Uani 1 d . . . H15 H 0.8995 -0.4705 0.2698 0.025 Uiso 1 calc R . . C16 C 0.6777(2) -0.29406(18) 0.30187(15) 0.0191(3) Uani 1 d . . . H16 H 0.6888 -0.2433 0.3632 0.023 Uiso 1 calc R . . C17 C 0.9080(3) -0.7123(2) 0.01017(17) 0.0301(4) Uani 1 d . . . H17A H 1.0087 -0.8034 -0.0187 0.045 Uiso 1 calc R . . H17B H 0.9001 -0.6416 -0.056 0.045 Uiso 1 calc R . . H17C H 0.8083 -0.7447 0.0399 0.045 Uiso 1 calc R . . C18 C -0.1529(2) 0.3932(2) 0.56324(15) 0.0239(4) Uani 1 d . . . H18A H -0.2715 0.4349 0.5701 0.036 Uiso 0.5 calc PR . . H18B H -0.1049 0.477 0.5466 0.036 Uiso 0.5 calc PR . . H18C H -0.1435 0.3456 0.6388 0.036 Uiso 0.5 calc PR . . H18D H -0.0751 0.4034 0.6003 0.036 Uiso 0.5 calc PR . . H18E H -0.2417 0.3613 0.6237 0.036 Uiso 0.5 calc PR . . H18F H -0.2032 0.4927 0.5315 0.036 Uiso 0.5 calc PR . . C19 C 0.2651(2) 0.28786(19) 0.20062(14) 0.0183(3) Uani 1 d . . . C20 C 0.2800(2) 0.06054(19) 0.10139(14) 0.0189(3) Uani 1 d . . . N1 N -0.06175(17) 0.27676(15) 0.46513(12) 0.0176(3) Uani 1 d . . . N2 N 0.25420(19) 0.41583(17) 0.19184(13) 0.0255(3) Uani 1 d . . . N3 N 0.28008(19) 0.00548(19) 0.01842(13) 0.0277(4) Uani 1 d . . . O1 O 0.43644(14) 0.04149(13) 0.23021(10) 0.0188(3) Uani 1 d . . . O2 O 0.24363(13) -0.07106(12) 0.34418(10) 0.0173(3) Uani 1 d . . . O3 O 0.20490(15) 0.21270(14) 0.47561(10) 0.0219(3) Uani 1 d . . . O4 O 0.91792(15) -0.63518(14) 0.10572(11) 0.0261(3) Uani 1 d . . . 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 C1 0.0173(8) 0.0164(8) 0.0213(8) 0.0024(6) -0.0085(6) -0.0079(6) C2 0.0169(8) 0.0126(7) 0.0195(8) 0.0002(6) -0.0079(6) -0.0063(6) C3 0.0153(8) 0.0165(8) 0.0195(8) -0.0002(6) -0.0075(6) -0.0073(6) C4 0.0205(8) 0.0152(8) 0.0174(7) 0.0020(6) -0.0067(6) -0.0099(6) C5 0.0187(8) 0.0193(8) 0.0200(8) -0.0017(6) -0.0061(6) -0.0087(6) C6 0.0208(9) 0.0251(9) 0.0242(8) 0.0020(7) -0.0107(7) -0.0135(7) C7 0.0153(8) 0.0264(9) 0.0271(9) 0.0054(7) -0.0086(7) -0.0102(7) C8 0.0168(8) 0.0175(8) 0.0248(8) -0.0002(6) -0.0045(6) -0.0062(6) C9 0.0150(8) 0.0156(8) 0.0185(8) 0.0017(6) -0.0059(6) -0.0075(6) C10 0.0192(8) 0.0149(8) 0.0183(7) 0.0011(6) -0.0067(6) -0.0095(6) C11 0.0173(8) 0.0156(8) 0.0213(8) 0.0007(6) -0.0071(6) -0.0062(6) C12 0.0200(9) 0.0195(8) 0.0265(9) -0.0012(6) -0.0110(7) -0.0048(7) C13 0.0270(9) 0.0194(8) 0.0245(8) -0.0012(6) -0.0107(7) -0.0091(7) C14 0.0223(9) 0.0130(8) 0.0247(8) 0.0023(6) -0.0063(7) -0.0058(6) C15 0.0191(8) 0.0188(8) 0.0284(9) 0.0027(6) -0.0118(7) -0.0063(7) C16 0.0214(8) 0.0157(8) 0.0238(8) 0.0020(6) -0.0102(7) -0.0084(6) C17 0.0365(11) 0.0212(9) 0.0290(9) -0.0055(7) -0.0147(8) 0.0000(8) C18 0.0263(9) 0.0191(8) 0.0250(9) -0.0081(7) -0.0023(7) -0.0101(7) C19 0.0177(8) 0.0205(9) 0.0183(8) 0.0001(6) -0.0066(6) -0.0079(6) C20 0.0157(8) 0.0200(8) 0.0220(8) -0.0003(6) -0.0052(6) -0.0082(6) N1 0.0179(7) 0.0158(7) 0.0207(7) -0.0036(5) -0.0052(5) -0.0076(5) N2 0.0306(8) 0.0203(8) 0.0271(8) 0.0012(6) -0.0103(6) -0.0097(6) N3 0.0255(8) 0.0367(9) 0.0239(8) -0.0052(6) -0.0066(6) -0.0144(7) O1 0.0156(6) 0.0168(6) 0.0268(6) 0.0042(4) -0.0094(5) -0.0074(5) O2 0.0155(6) 0.0136(6) 0.0241(6) 0.0019(4) -0.0078(5) -0.0058(4) O3 0.0238(6) 0.0236(6) 0.0254(6) -0.0012(5) -0.0127(5) -0.0116(5) O4 0.0263(7) 0.0171(6) 0.0321(7) -0.0042(5) -0.0121(5) -0.0004(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O2 1.4223(19) . ? C1 O1 1.4726(18) . ? C1 C11 1.496(2) . ? C1 H1 1 . ? C2 O2 1.4208(19) . ? C2 C9 1.494(2) . ? C2 C4 1.562(2) . ? C2 C3 1.581(2) . ? C3 O1 1.3997(19) . ? C3 C19 1.489(2) . ? C3 C20 1.492(2) . ? C4 O3 1.2236(19) . ? C4 N1 1.355(2) . ? C5 C9 1.386(2) . ? C5 C6 1.393(2) . ? C5 H5 0.95 . ? C6 C7 1.392(2) . ? C6 H6 0.95 . ? C7 C8 1.402(2) . ? C7 H7 0.95 . ? C8 C10 1.379(2) . ? C8 H8 0.95 . ? C9 C10 1.400(2) . ? C10 N1 1.416(2) . ? C11 C12 1.391(2) . ? C11 C16 1.394(2) . ? C12 C13 1.390(2) . ? C12 H12 0.95 . ? C13 C14 1.398(2) . ? C13 H13 0.95 . ? C14 O4 1.365(2) . ? C14 C15 1.396(2) . ? C15 C16 1.389(2) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 O4 1.434(2) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? C18 N1 1.462(2) . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C18 H18D 0.98 . ? C18 H18E 0.98 . ? C18 H18F 0.98 . ? C19 N2 1.146(2) . ? C20 N3 1.147(2) . ? 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 O2 C1 O1 104.61(11) . . ? O2 C1 C11 112.23(12) . . ? O1 C1 C11 109.84(12) . . ? O2 C1 H1 110 . . ? O1 C1 H1 110 . . ? C11 C1 H1 110 . . ? O2 C2 C9 113.91(12) . . ? O2 C2 C4 113.65(12) . . ? C9 C2 C4 103.18(12) . . ? O2 C2 C3 99.04(11) . . ? C9 C2 C3 118.29(12) . . ? C4 C2 C3 109.19(12) . . ? O1 C3 C19 108.50(12) . . ? O1 C3 C20 110.37(13) . . ? C19 C3 C20 109.49(13) . . ? O1 C3 C2 103.58(12) . . ? C19 C3 C2 114.19(13) . . ? C20 C3 C2 110.54(12) . . ? O3 C4 N1 127.64(15) . . ? O3 C4 C2 125.48(14) . . ? N1 C4 C2 106.87(13) . . ? C9 C5 C6 118.46(15) . . ? C9 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C7 C6 C5 120.61(15) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 121.34(15) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C10 C8 C7 117.27(15) . . ? C10 C8 H8 121.4 . . ? C7 C8 H8 121.4 . . ? C5 C9 C10 120.34(15) . . ? C5 C9 C2 131.81(15) . . ? C10 C9 C2 107.85(13) . . ? C8 C10 C9 121.94(14) . . ? C8 C10 N1 128.01(15) . . ? C9 C10 N1 110.05(14) . . ? C12 C11 C16 119.28(15) . . ? C12 C11 C1 121.59(14) . . ? C16 C11 C1 118.92(14) . . ? C13 C12 C11 121.08(15) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 119.32(15) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? O4 C14 C15 116.04(15) . . ? O4 C14 C13 124.14(15) . . ? C15 C14 C13 119.83(15) . . ? C16 C15 C14 120.25(15) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 120.20(15) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C18 H18D 109.5 . . ? H18A C18 H18D 141.1 . . ? H18B C18 H18D 56.3 . . ? H18C C18 H18D 56.3 . . ? N1 C18 H18E 109.5 . . ? H18A C18 H18E 56.3 . . ? H18B C18 H18E 141.1 . . ? H18C C18 H18E 56.3 . . ? H18D C18 H18E 109.5 . . ? N1 C18 H18F 109.5 . . ? H18A C18 H18F 56.3 . . ? H18B C18 H18F 56.3 . . ? H18C C18 H18F 141.1 . . ? H18D C18 H18F 109.5 . . ? H18E C18 H18F 109.5 . . ? N2 C19 C3 178.44(17) . . ? N3 C20 C3 175.87(17) . . ? C4 N1 C10 111.57(13) . . ? C4 N1 C18 123.72(14) . . ? C10 N1 C18 124.30(14) . . ? C3 O1 C1 108.81(11) . . ? C2 O2 C1 108.12(11) . . ? C14 O4 C17 117.28(13) . . ? 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 O2 C2 C3 O1 -35.18(13) . . . . ? C9 C2 C3 O1 -158.66(13) . . . . ? C4 C2 C3 O1 83.86(14) . . . . ? O2 C2 C3 C19 -152.98(12) . . . . ? C9 C2 C3 C19 83.54(17) . . . . ? C4 C2 C3 C19 -33.94(17) . . . . ? O2 C2 C3 C20 83.05(14) . . . . ? C9 C2 C3 C20 -40.43(18) . . . . ? C4 C2 C3 C20 -157.91(13) . . . . ? O2 C2 C4 O3 50.4(2) . . . . ? C9 C2 C4 O3 174.20(14) . . . . ? C3 C2 C4 O3 -59.16(19) . . . . ? O2 C2 C4 N1 -130.79(13) . . . . ? C9 C2 C4 N1 -6.94(15) . . . . ? C3 C2 C4 N1 119.70(13) . . . . ? C9 C5 C6 C7 -0.9(2) . . . . ? C5 C6 C7 C8 -0.5(2) . . . . ? C6 C7 C8 C10 0.5(2) . . . . ? C6 C5 C9 C10 2.3(2) . . . . ? C6 C5 C9 C2 -177.99(15) . . . . ? O2 C2 C9 C5 -50.2(2) . . . . ? C4 C2 C9 C5 -173.90(16) . . . . ? C3 C2 C9 C5 65.5(2) . . . . ? O2 C2 C9 C10 129.52(14) . . . . ? C4 C2 C9 C10 5.85(15) . . . . ? C3 C2 C9 C10 -114.77(15) . . . . ? C7 C8 C10 C9 0.9(2) . . . . ? C7 C8 C10 N1 -178.14(14) . . . . ? C5 C9 C10 C8 -2.3(2) . . . . ? C2 C9 C10 C8 177.88(14) . . . . ? C5 C9 C10 N1 176.85(13) . . . . ? C2 C9 C10 N1 -2.94(17) . . . . ? O2 C1 C11 C12 43.1(2) . . . . ? O1 C1 C11 C12 -72.83(18) . . . . ? O2 C1 C11 C16 -142.24(14) . . . . ? O1 C1 C11 C16 101.84(16) . . . . ? C16 C11 C12 C13 -1.0(2) . . . . ? C1 C11 C12 C13 173.63(15) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? C12 C13 C14 O4 -178.31(15) . . . . ? C12 C13 C14 C15 1.8(2) . . . . ? O4 C14 C15 C16 178.69(15) . . . . ? C13 C14 C15 C16 -1.4(2) . . . . ? C14 C15 C16 C11 -0.2(2) . . . . ? C12 C11 C16 C15 1.4(2) . . . . ? C1 C11 C16 C15 -173.36(15) . . . . ? O1 C3 C19 N2 -3(7) . . . . ? C20 C3 C19 N2 -123(6) . . . . ? C2 C3 C19 N2 112(6) . . . . ? O1 C3 C20 N3 51(2) . . . . ? C19 C3 C20 N3 170(2) . . . . ? C2 C3 C20 N3 -63(2) . . . . ? O3 C4 N1 C10 -175.60(15) . . . . ? C2 C4 N1 C10 5.58(16) . . . . ? O3 C4 N1 C18 -2.7(3) . . . . ? C2 C4 N1 C18 178.44(13) . . . . ? C8 C10 N1 C4 177.26(16) . . . . ? C9 C10 N1 C4 -1.86(18) . . . . ? C8 C10 N1 C18 4.4(3) . . . . ? C9 C10 N1 C18 -174.68(14) . . . . ? C19 C3 O1 C1 140.74(12) . . . . ? C20 C3 O1 C1 -99.29(14) . . . . ? C2 C3 O1 C1 19.05(14) . . . . ? O2 C1 O1 C3 4.33(15) . . . . ? C11 C1 O1 C3 124.97(13) . . . . ? C9 C2 O2 C1 165.85(12) . . . . ? C4 C2 O2 C1 -76.36(15) . . . . ? C3 C2 O2 C1 39.30(14) . . . . ? O1 C1 O2 C2 -29.36(15) . . . . ? C11 C1 O2 C2 -148.40(13) . . . . ? C15 C14 O4 C17 -177.85(14) . . . . ? C13 C14 O4 C17 2.3(2) . . . . ? #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-06-11 at 14:44:02 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\progs\wingx\files\archive.dat # CIF files read : job struct data_16a _database_code_depnum_ccdc_archive 'CCDC 654061' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H10 Cl1 N3 O3' _chemical_formula_sum 'C18 H10 Cl N3 O3' _chemical_formula_weight 351.74 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4444(5) _cell_length_b 8.6287(6) _cell_length_c 12.8065(8) _cell_angle_alpha 71.202(3) _cell_angle_beta 87.399(3) _cell_angle_gamma 83.872(3) _cell_volume 774.25(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6431 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.49 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.17 _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.868 _exptl_absorpt_correction_T_max 0.955 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_unetI/netI 0.0331 _diffrn_reflns_number 11851 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 3524 _reflns_number_gt 3302 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0398P)^2^+0.4531P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3524 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.041 _refine_ls_R_factor_gt 0.038 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0917 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.434 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.052 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.07878(19) 0.65376(17) 0.62329(11) 0.0146(3) Uani 1 d . . . H1 H -0.0558 0.6639 0.6176 0.017 Uiso 1 calc R . . C2 C 0.20329(18) 0.49844(17) 0.79267(11) 0.0136(3) Uani 1 d . . . C3 C 0.28700(18) 0.43216(17) 0.69794(11) 0.0137(3) Uani 1 d . . . C4 C 0.3437(2) 0.51619(18) 0.87393(12) 0.0155(3) Uani 1 d . . . C5 C -0.08194(19) 0.33081(18) 0.84945(12) 0.0157(3) Uani 1 d . . . H5 H -0.1301 0.3619 0.7774 0.019 Uiso 1 calc R . . C6 C -0.16772(19) 0.22666(18) 0.94016(12) 0.0169(3) Uani 1 d . . . C7 C -0.1006(2) 0.18016(18) 1.04671(12) 0.0180(3) Uani 1 d . . . H7 H -0.1627 0.1086 1.1063 0.022 Uiso 1 calc R . . C8 C 0.0581(2) 0.23878(18) 1.06585(12) 0.0173(3) Uani 1 d . . . H8 H 0.1056 0.2092 1.138 0.021 Uiso 1 calc R . . C9 C 0.07660(19) 0.38675(17) 0.86921(11) 0.0136(3) Uani 1 d . . . C10 C 0.14374(19) 0.34140(17) 0.97619(11) 0.0143(3) Uani 1 d . . . C11 C 0.15329(18) 0.79409(17) 0.53379(11) 0.0146(3) Uani 1 d . . . C12 C 0.22648(19) 0.92016(18) 0.55809(12) 0.0181(3) Uani 1 d . . . H12 H 0.2327 0.9184 0.6324 0.022 Uiso 1 calc R . . C13 C 0.2905(2) 1.04900(19) 0.47263(13) 0.0212(3) Uani 1 d . . . H13 H 0.3391 1.136 0.4888 0.025 Uiso 1 calc R . . C14 C 0.2838(2) 1.0511(2) 0.36411(13) 0.0241(3) Uani 1 d . . . H14 H 0.3298 1.138 0.3063 0.029 Uiso 1 calc R . . C15 C 0.2093(3) 0.9253(2) 0.34042(13) 0.0275(4) Uani 1 d . . . H15 H 0.2037 0.9268 0.2661 0.033 Uiso 1 calc R . . C16 C 0.1428(2) 0.7973(2) 0.42510(13) 0.0223(3) Uani 1 d . . . H16 H 0.0905 0.7123 0.4086 0.027 Uiso 1 calc R . . C17 C 0.30448(19) 0.25070(18) 0.72813(11) 0.0155(3) Uani 1 d . . . C18 C 0.46587(19) 0.49403(17) 0.65670(12) 0.0158(3) Uani 1 d . . . N1 N 0.30100(17) 0.41885(15) 0.97580(10) 0.0156(3) Uani 1 d . . . HN1 H 0.365(3) 0.407(3) 1.029(2) 0.05 Uiso 1 d . . . N2 N 0.31689(18) 0.11033(16) 0.75102(11) 0.0218(3) Uani 1 d . . . N3 N 0.60368(18) 0.53643(17) 0.62361(11) 0.0228(3) Uani 1 d . . . O1 O 0.15270(14) 0.49482(12) 0.61664(8) 0.0153(2) Uani 1 d . . . O2 O 0.12596(14) 0.65591(12) 0.72987(8) 0.0165(2) Uani 1 d . . . O3 O 0.46840(15) 0.60288(13) 0.84748(8) 0.0206(2) Uani 1 d . . . Cl1 Cl -0.36713(5) 0.15126(5) 0.92034(3) 0.02198(11) Uani 1 d . . . 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 C1 0.0158(6) 0.0147(7) 0.0139(6) -0.0056(5) 0.0006(5) -0.0015(5) C2 0.0156(6) 0.0128(7) 0.0126(6) -0.0038(5) 0.0005(5) -0.0031(5) C3 0.0148(6) 0.0136(7) 0.0129(6) -0.0040(5) 0.0005(5) -0.0035(5) C4 0.0196(7) 0.0148(7) 0.0139(6) -0.0070(5) 0.0009(5) -0.0024(5) C5 0.0174(7) 0.0163(7) 0.0137(6) -0.0052(5) 0.0016(5) -0.0023(5) C6 0.0150(6) 0.0156(7) 0.0218(7) -0.0079(6) 0.0041(5) -0.0036(5) C7 0.0211(7) 0.0149(7) 0.0168(7) -0.0034(6) 0.0063(6) -0.0036(6) C8 0.0224(7) 0.0155(7) 0.0125(6) -0.0034(5) 0.0013(5) -0.0001(6) C9 0.0166(7) 0.0121(7) 0.0120(6) -0.0038(5) 0.0036(5) -0.0024(5) C10 0.0165(6) 0.0129(7) 0.0144(7) -0.0059(5) 0.0012(5) -0.0015(5) C11 0.0133(6) 0.0142(7) 0.0139(6) -0.0021(5) 0.0005(5) 0.0009(5) C12 0.0166(7) 0.0181(7) 0.0188(7) -0.0045(6) -0.0025(5) -0.0018(6) C13 0.0168(7) 0.0167(7) 0.0271(8) -0.0022(6) -0.0007(6) -0.0033(6) C14 0.0219(7) 0.0193(8) 0.0230(8) 0.0026(6) 0.0080(6) 0.0003(6) C15 0.0411(10) 0.0240(9) 0.0150(7) -0.0049(6) 0.0059(7) 0.0013(7) C16 0.0320(8) 0.0184(8) 0.0170(7) -0.0066(6) 0.0008(6) -0.0020(6) C17 0.0152(6) 0.0181(7) 0.0141(7) -0.0060(6) 0.0024(5) -0.0046(5) C18 0.0189(7) 0.0135(7) 0.0153(7) -0.0051(5) 0.0020(5) -0.0024(5) N1 0.0176(6) 0.0170(6) 0.0127(6) -0.0045(5) -0.0008(4) -0.0046(5) N2 0.0252(7) 0.0178(7) 0.0225(7) -0.0065(5) 0.0024(5) -0.0042(5) N3 0.0223(7) 0.0203(7) 0.0260(7) -0.0072(6) 0.0049(5) -0.0057(5) O1 0.0198(5) 0.0134(5) 0.0135(5) -0.0048(4) -0.0028(4) -0.0016(4) O2 0.0247(5) 0.0131(5) 0.0112(5) -0.0034(4) -0.0001(4) -0.0006(4) O3 0.0250(6) 0.0231(6) 0.0159(5) -0.0061(4) 0.0007(4) -0.0125(4) Cl1 0.01687(18) 0.0242(2) 0.0262(2) -0.00845(15) 0.00471(14) -0.00886(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O2 1.4310(16) . ? C1 O1 1.4495(17) . ? C1 C11 1.5096(19) . ? C1 H1 1 . ? C2 O2 1.4125(17) . ? C2 C9 1.5102(18) . ? C2 C4 1.5603(19) . ? C2 C3 1.5778(19) . ? C3 O1 1.4115(16) . ? C3 C17 1.480(2) . ? C3 C18 1.4977(19) . ? C4 O3 1.2217(17) . ? C4 N1 1.3497(19) . ? C5 C9 1.3847(19) . ? C5 C6 1.395(2) . ? C5 H5 0.95 . ? C6 C7 1.393(2) . ? C6 Cl1 1.7431(14) . ? C7 C8 1.395(2) . ? C7 H7 0.95 . ? C8 C10 1.381(2) . ? C8 H8 0.95 . ? C9 C10 1.3981(19) . ? C10 N1 1.4077(18) . ? C11 C16 1.389(2) . ? C11 C12 1.392(2) . ? C12 C13 1.394(2) . ? C12 H12 0.95 . ? C13 C14 1.387(2) . ? C13 H13 0.95 . ? C14 C15 1.390(2) . ? C14 H14 0.95 . ? C15 C16 1.392(2) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 N2 1.1451(19) . ? C18 N3 1.1432(19) . ? N1 HN1 0.82(3) . ? 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 O2 C1 O1 105.95(11) . . ? O2 C1 C11 110.57(11) . . ? O1 C1 C11 112.16(11) . . ? O2 C1 H1 109.4 . . ? O1 C1 H1 109.4 . . ? C11 C1 H1 109.4 . . ? O2 C2 C9 116.29(12) . . ? O2 C2 C4 109.56(11) . . ? C9 C2 C4 102.48(11) . . ? O2 C2 C3 100.57(10) . . ? C9 C2 C3 113.67(11) . . ? C4 C2 C3 114.79(11) . . ? O1 C3 C17 107.72(11) . . ? O1 C3 C18 111.74(11) . . ? C17 C3 C18 109.20(12) . . ? O1 C3 C2 101.24(11) . . ? C17 C3 C2 113.75(11) . . ? C18 C3 C2 112.90(11) . . ? O3 C4 N1 127.67(13) . . ? O3 C4 C2 124.99(13) . . ? N1 C4 C2 107.34(11) . . ? C9 C5 C6 117.00(13) . . ? C9 C5 H5 121.5 . . ? C6 C5 H5 121.5 . . ? C7 C6 C5 122.61(13) . . ? C7 C6 Cl1 118.27(11) . . ? C5 C6 Cl1 119.12(11) . . ? C6 C7 C8 119.90(13) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C10 C8 C7 117.64(13) . . ? C10 C8 H8 121.2 . . ? C7 C8 H8 121.2 . . ? C5 C9 C10 120.56(13) . . ? C5 C9 C2 131.47(12) . . ? C10 C9 C2 107.96(12) . . ? C8 C10 C9 122.28(13) . . ? C8 C10 N1 127.74(13) . . ? C9 C10 N1 109.96(12) . . ? C16 C11 C12 120.23(13) . . ? C16 C11 C1 118.28(13) . . ? C12 C11 C1 121.46(13) . . ? C11 C12 C13 119.53(14) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 120.45(14) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.68(14) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 120.25(15) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C11 C16 C15 119.83(15) . . ? C11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? N2 C17 C3 179.48(16) . . ? N3 C18 C3 177.39(15) . . ? C4 N1 C10 112.13(12) . . ? C4 N1 HN1 121.5(17) . . ? C10 N1 HN1 126.3(17) . . ? C3 O1 C1 107.10(10) . . ? C2 O2 C1 109.67(10) . . ? 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 O2 C2 C3 O1 -38.32(12) . . . . ? C9 C2 C3 O1 86.69(13) . . . . ? C4 C2 C3 O1 -155.78(11) . . . . ? O2 C2 C3 C17 -153.56(11) . . . . ? C9 C2 C3 C17 -28.55(16) . . . . ? C4 C2 C3 C17 88.98(14) . . . . ? O2 C2 C3 C18 81.28(13) . . . . ? C9 C2 C3 C18 -153.72(12) . . . . ? C4 C2 C3 C18 -36.19(16) . . . . ? O2 C2 C4 O3 -52.72(19) . . . . ? C9 C2 C4 O3 -176.77(14) . . . . ? C3 C2 C4 O3 59.52(19) . . . . ? O2 C2 C4 N1 127.56(12) . . . . ? C9 C2 C4 N1 3.51(15) . . . . ? C3 C2 C4 N1 -120.21(13) . . . . ? C9 C5 C6 C7 0.5(2) . . . . ? C9 C5 C6 Cl1 -179.63(11) . . . . ? C5 C6 C7 C8 0.3(2) . . . . ? Cl1 C6 C7 C8 -179.64(11) . . . . ? C6 C7 C8 C10 -0.5(2) . . . . ? C6 C5 C9 C10 -1.0(2) . . . . ? C6 C5 C9 C2 179.89(14) . . . . ? O2 C2 C9 C5 56.6(2) . . . . ? C4 C2 C9 C5 176.06(15) . . . . ? C3 C2 C9 C5 -59.5(2) . . . . ? O2 C2 C9 C10 -122.61(13) . . . . ? C4 C2 C9 C10 -3.16(15) . . . . ? C3 C2 C9 C10 121.30(13) . . . . ? C7 C8 C10 C9 0.0(2) . . . . ? C7 C8 C10 N1 177.92(14) . . . . ? C5 C9 C10 C8 0.8(2) . . . . ? C2 C9 C10 C8 -179.91(13) . . . . ? C5 C9 C10 N1 -177.49(13) . . . . ? C2 C9 C10 N1 1.83(16) . . . . ? O2 C1 C11 C16 170.91(13) . . . . ? O1 C1 C11 C16 52.90(17) . . . . ? O2 C1 C11 C12 -10.82(19) . . . . ? O1 C1 C11 C12 -128.82(14) . . . . ? C16 C11 C12 C13 -0.5(2) . . . . ? C1 C11 C12 C13 -178.75(13) . . . . ? C11 C12 C13 C14 -0.8(2) . . . . ? C12 C13 C14 C15 1.3(2) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C12 C11 C16 C15 1.3(2) . . . . ? C1 C11 C16 C15 179.64(14) . . . . ? C14 C15 C16 C11 -0.9(3) . . . . ? O1 C3 C17 N2 -1E1(2) . . . . ? C18 C3 C17 N2 -13E1(2) . . . . ? C2 C3 C17 N2 10E1(2) . . . . ? O1 C3 C18 N3 -86(4) . . . . ? C17 C3 C18 N3 33(4) . . . . ? C2 C3 C18 N3 161(4) . . . . ? O3 C4 N1 C10 177.64(15) . . . . ? C2 C4 N1 C10 -2.65(16) . . . . ? C8 C10 N1 C4 -177.55(15) . . . . ? C9 C10 N1 C4 0.59(17) . . . . ? C17 C3 O1 C1 154.65(11) . . . . ? C18 C3 O1 C1 -85.41(13) . . . . ? C2 C3 O1 C1 35.01(12) . . . . ? O2 C1 O1 C3 -19.10(13) . . . . ? C11 C1 O1 C3 101.62(12) . . . . ? C9 C2 O2 C1 -95.28(13) . . . . ? C4 C2 O2 C1 149.18(11) . . . . ? C3 C2 O2 C1 27.93(13) . . . . ? O1 C1 O2 C2 -7.75(14) . . . . ? C11 C1 O2 C2 -129.49(12) . . . . ? #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-06-11 at 14:31:56 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\progs\wingx\files\archive.dat # CIF files read : job struct data_10a _database_code_depnum_ccdc_archive 'CCDC 654062' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H9 Cl2 N3 O3' _chemical_formula_sum 'C18 H9 Cl2 N3 O3' _chemical_formula_weight 386.18 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2738(8) _cell_length_b 9.1406(9) _cell_length_c 12.8097(14) _cell_angle_alpha 72.904(4) _cell_angle_beta 87.391(4) _cell_angle_gamma 83.669(4) _cell_volume 809.00(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8107 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.37 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.426 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.831 _exptl_absorpt_correction_T_max 0.926 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_unetI/netI 0.0228 _diffrn_reflns_number 13152 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.951 _reflns_number_total 3529 _reflns_number_gt 3146 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0317P)^2^+0.5206P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3529 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0691 _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_restrained_S_all 1.03 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.442 _refine_diff_density_min -0.23 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.94220(19) -0.13972(16) 0.36480(11) 0.0134(3) Uani 1 d . . . H1 H 1.0801 -0.1536 0.3702 0.016 Uiso 1 calc R . . C2 C 0.81475(19) 0.01293(15) 0.20061(11) 0.0126(3) Uani 1 d . . . C3 C 0.73441(18) 0.07314(15) 0.29839(11) 0.0124(3) Uani 1 d . . . C4 C 0.66871(19) 0.00092(16) 0.11863(11) 0.0138(3) Uani 1 d . . . C5 C 1.10588(19) 0.16894(16) 0.15024(11) 0.0142(3) Uani 1 d . . . H5 H 1.1557 0.1366 0.2216 0.017 Uiso 1 calc R . . C6 C 1.19120(19) 0.27106(16) 0.06399(11) 0.0152(3) Uani 1 d . . . C7 C 1.1215(2) 0.31975(17) -0.04097(11) 0.0166(3) Uani 1 d . . . H7 H 1.1833 0.3904 -0.0975 0.02 Uiso 1 calc R . . C8 C 0.9605(2) 0.26501(16) -0.06367(11) 0.0158(3) Uani 1 d . . . H8 H 0.9113 0.2966 -0.1352 0.019 Uiso 1 calc R . . C9 C 0.94505(19) 0.11642(16) 0.12743(11) 0.0126(3) Uani 1 d . . . C10 C 0.87546(19) 0.16348(16) 0.02156(11) 0.0132(3) Uani 1 d . . . C11 C 0.86125(18) -0.26972(16) 0.44968(11) 0.0128(3) Uani 1 d . . . C12 C 0.79790(18) -0.39121(16) 0.42139(11) 0.0139(3) Uani 1 d . . . H12 H 0.8021 -0.3918 0.3473 0.017 Uiso 1 calc R . . C13 C 0.72860(19) -0.51132(16) 0.50159(11) 0.0146(3) Uani 1 d . . . H13 H 0.6862 -0.595 0.483 0.017 Uiso 1 calc R . . C14 C 0.72188(19) -0.50791(16) 0.60910(11) 0.0145(3) Uani 1 d . . . C15 C 0.7854(2) -0.38822(17) 0.63902(11) 0.0165(3) Uani 1 d . . . H15 H 0.7805 -0.3878 0.7132 0.02 Uiso 1 calc R . . C16 C 0.85605(19) -0.26935(16) 0.55839(11) 0.0156(3) Uani 1 d . . . H16 H 0.9012 -0.1871 0.5775 0.019 Uiso 1 calc R . . C17 C 0.72477(19) 0.24227(16) 0.27529(11) 0.0143(3) Uani 1 d . . . C18 C 0.55009(19) 0.02003(16) 0.33953(11) 0.0144(3) Uani 1 d . . . N1 N 0.71457(16) 0.09129(14) 0.01917(10) 0.0142(2) Uani 1 d . . . HN1 H 0.653(3) 0.103(3) -0.035(2) 0.05 Uiso 1 d . . . N2 N 0.72273(18) 0.37242(15) 0.25854(10) 0.0207(3) Uani 1 d . . . N3 N 0.40920(17) -0.01698(15) 0.37403(10) 0.0205(3) Uani 1 d . . . O1 O 0.87264(13) 0.00876(11) 0.37763(8) 0.0133(2) Uani 1 d . . . O2 O 0.89094(14) -0.13684(11) 0.25801(8) 0.0151(2) Uani 1 d . . . O3 O 0.53969(14) -0.07751(12) 0.14283(8) 0.0185(2) Uani 1 d . . . Cl1 Cl 0.63078(5) -0.65778(4) 0.70863(3) 0.01733(9) Uani 1 d . . . Cl2 Cl 1.39052(5) 0.34456(4) 0.08931(3) 0.01951(10) Uani 1 d . . . 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 C1 0.0133(6) 0.0140(7) 0.0141(6) -0.0064(5) -0.0019(5) 0.0007(5) C2 0.0132(6) 0.0124(6) 0.0131(6) -0.0048(5) -0.0010(5) -0.0016(5) C3 0.0121(6) 0.0129(6) 0.0129(6) -0.0045(5) -0.0015(5) -0.0014(5) C4 0.0140(6) 0.0139(6) 0.0153(6) -0.0073(5) -0.0013(5) -0.0004(5) C5 0.0132(6) 0.0157(7) 0.0145(6) -0.0057(5) -0.0016(5) -0.0007(6) C6 0.0118(6) 0.0159(7) 0.0202(7) -0.0086(5) 0.0012(5) -0.0026(5) C7 0.0171(7) 0.0165(7) 0.0167(7) -0.0054(5) 0.0033(5) -0.0031(6) C8 0.0183(7) 0.0160(7) 0.0133(6) -0.0045(5) -0.0014(5) -0.0010(6) C9 0.0127(6) 0.0120(6) 0.0139(6) -0.0051(5) 0.0002(5) -0.0001(5) C10 0.0123(6) 0.0134(6) 0.0156(6) -0.0074(5) -0.0005(5) -0.0003(5) C11 0.0094(6) 0.0128(6) 0.0156(6) -0.0040(5) -0.0026(5) 0.0023(5) C12 0.0117(6) 0.0159(7) 0.0146(6) -0.0061(5) -0.0035(5) 0.0021(5) C13 0.0127(6) 0.0124(7) 0.0197(7) -0.0064(5) -0.0038(5) 0.0007(5) C14 0.0112(6) 0.0132(7) 0.0173(7) -0.0022(5) -0.0016(5) 0.0014(5) C15 0.0190(7) 0.0168(7) 0.0145(6) -0.0064(5) -0.0008(5) -0.0001(6) C16 0.0167(7) 0.0140(7) 0.0178(7) -0.0073(5) -0.0016(5) -0.0010(6) C17 0.0129(6) 0.0173(7) 0.0139(6) -0.0061(5) -0.0018(5) -0.0014(6) C18 0.0160(7) 0.0139(7) 0.0145(6) -0.0064(5) -0.0020(5) 0.0002(6) N1 0.0133(6) 0.0171(6) 0.0133(5) -0.0056(5) -0.0023(4) -0.0028(5) N2 0.0217(7) 0.0179(7) 0.0232(6) -0.0072(5) -0.0028(5) -0.0013(5) N3 0.0173(6) 0.0224(7) 0.0240(6) -0.0101(5) 0.0023(5) -0.0036(5) O1 0.0144(5) 0.0114(5) 0.0146(5) -0.0046(4) -0.0048(4) 0.0006(4) O2 0.0207(5) 0.0123(5) 0.0122(5) -0.0040(4) -0.0016(4) 0.0007(4) O3 0.0183(5) 0.0221(5) 0.0172(5) -0.0065(4) -0.0011(4) -0.0090(4) Cl1 0.01683(17) 0.01543(17) 0.01763(17) -0.00120(13) -0.00098(12) -0.00236(13) Cl2 0.01483(17) 0.02349(19) 0.02266(18) -0.00833(14) 0.00132(12) -0.00853(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O2 1.4263(16) . ? C1 O1 1.4482(17) . ? C1 C11 1.5090(18) . ? C1 H1 1 . ? C2 O2 1.4141(17) . ? C2 C9 1.5058(18) . ? C2 C4 1.5615(18) . ? C2 C3 1.5751(19) . ? C3 O1 1.4138(16) . ? C3 C17 1.4804(19) . ? C3 C18 1.4965(18) . ? C4 O3 1.2174(16) . ? C4 N1 1.3492(18) . ? C5 C9 1.3864(18) . ? C5 C6 1.3914(19) . ? C5 H5 0.95 . ? C6 C7 1.387(2) . ? C6 Cl2 1.7447(14) . ? C7 C8 1.3975(19) . ? C7 H7 0.95 . ? C8 C10 1.3802(19) . ? C8 H8 0.95 . ? C9 C10 1.3971(18) . ? C10 N1 1.4112(17) . ? C11 C16 1.3924(19) . ? C11 C12 1.3934(19) . ? C12 C13 1.3880(19) . ? C12 H12 0.95 . ? C13 C14 1.385(2) . ? C13 H13 0.95 . ? C14 C15 1.390(2) . ? C14 Cl1 1.7429(14) . ? C15 C16 1.3880(19) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 N2 1.1436(19) . ? C18 N3 1.1434(19) . ? N1 HN1 0.82(2) . ? 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 O2 C1 O1 106.12(10) . . ? O2 C1 C11 110.32(10) . . ? O1 C1 C11 111.78(11) . . ? O2 C1 H1 109.5 . . ? O1 C1 H1 109.5 . . ? C11 C1 H1 109.5 . . ? O2 C2 C9 116.63(12) . . ? O2 C2 C4 109.03(10) . . ? C9 C2 C4 102.53(10) . . ? O2 C2 C3 100.55(10) . . ? C9 C2 C3 113.22(11) . . ? C4 C2 C3 115.41(11) . . ? O1 C3 C17 106.91(10) . . ? O1 C3 C18 111.29(11) . . ? C17 C3 C18 109.49(12) . . ? O1 C3 C2 101.31(11) . . ? C17 C3 C2 113.84(11) . . ? C18 C3 C2 113.56(10) . . ? O3 C4 N1 127.91(13) . . ? O3 C4 C2 124.86(12) . . ? N1 C4 C2 107.23(11) . . ? C9 C5 C6 117.08(12) . . ? C9 C5 H5 121.5 . . ? C6 C5 H5 121.5 . . ? C7 C6 C5 122.57(12) . . ? C7 C6 Cl2 118.58(10) . . ? C5 C6 Cl2 118.83(11) . . ? C6 C7 C8 120.05(13) . . ? C6 C7 H7 120 . . ? C8 C7 H7 120 . . ? C10 C8 C7 117.61(13) . . ? C10 C8 H8 121.2 . . ? C7 C8 H8 121.2 . . ? C5 C9 C10 120.62(12) . . ? C5 C9 C2 131.12(12) . . ? C10 C9 C2 108.23(11) . . ? C8 C10 C9 122.05(12) . . ? C8 C10 N1 128.28(12) . . ? C9 C10 N1 109.67(12) . . ? C16 C11 C12 120.00(12) . . ? C16 C11 C1 118.81(12) . . ? C12 C11 C1 121.16(12) . . ? C13 C12 C11 119.93(12) . . ? C13 C12 H12 120 . . ? C11 C12 H12 120 . . ? C14 C13 C12 119.29(13) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 121.63(13) . . ? C13 C14 Cl1 118.81(11) . . ? C15 C14 Cl1 119.56(11) . . ? C16 C15 C14 118.66(13) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C11 120.48(13) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? N2 C17 C3 177.92(15) . . ? N3 C18 C3 177.10(15) . . ? C4 N1 C10 112.23(11) . . ? C4 N1 HN1 122.6(17) . . ? C10 N1 HN1 125.1(17) . . ? C3 O1 C1 106.94(10) . . ? C2 O2 C1 109.74(10) . . ? 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 O2 C2 C3 O1 38.10(11) . . . . ? C9 C2 C3 O1 -87.07(13) . . . . ? C4 C2 C3 O1 155.21(10) . . . . ? O2 C2 C3 C17 152.48(11) . . . . ? C9 C2 C3 C17 27.31(16) . . . . ? C4 C2 C3 C17 -90.41(13) . . . . ? O2 C2 C3 C18 -81.31(13) . . . . ? C9 C2 C3 C18 153.52(12) . . . . ? C4 C2 C3 C18 35.79(16) . . . . ? O2 C2 C4 O3 52.94(18) . . . . ? C9 C2 C4 O3 177.16(14) . . . . ? C3 C2 C4 O3 -59.28(18) . . . . ? O2 C2 C4 N1 -126.64(12) . . . . ? C9 C2 C4 N1 -2.41(14) . . . . ? C3 C2 C4 N1 121.14(13) . . . . ? C9 C5 C6 C7 -0.1(2) . . . . ? C9 C5 C6 Cl2 178.27(11) . . . . ? C5 C6 C7 C8 -0.6(2) . . . . ? Cl2 C6 C7 C8 -178.99(11) . . . . ? C6 C7 C8 C10 0.5(2) . . . . ? C6 C5 C9 C10 1.0(2) . . . . ? C6 C5 C9 C2 -176.89(14) . . . . ? O2 C2 C9 C5 -59.5(2) . . . . ? C4 C2 C9 C5 -178.56(15) . . . . ? C3 C2 C9 C5 56.4(2) . . . . ? O2 C2 C9 C10 122.41(13) . . . . ? C4 C2 C9 C10 3.39(15) . . . . ? C3 C2 C9 C10 -121.61(12) . . . . ? C7 C8 C10 C9 0.4(2) . . . . ? C7 C8 C10 N1 -179.10(14) . . . . ? C5 C9 C10 C8 -1.1(2) . . . . ? C2 C9 C10 C8 177.17(13) . . . . ? C5 C9 C10 N1 178.45(13) . . . . ? C2 C9 C10 N1 -3.26(16) . . . . ? O2 C1 C11 C16 -164.26(12) . . . . ? O1 C1 C11 C16 -46.43(17) . . . . ? O2 C1 C11 C12 17.81(18) . . . . ? O1 C1 C11 C12 135.65(13) . . . . ? C16 C11 C12 C13 0.4(2) . . . . ? C1 C11 C12 C13 178.29(13) . . . . ? C11 C12 C13 C14 0.6(2) . . . . ? C12 C13 C14 C15 -1.0(2) . . . . ? C12 C13 C14 Cl1 178.88(10) . . . . ? C13 C14 C15 C16 0.4(2) . . . . ? Cl1 C14 C15 C16 -179.49(11) . . . . ? C14 C15 C16 C11 0.6(2) . . . . ? C12 C11 C16 C15 -1.0(2) . . . . ? C1 C11 C16 C15 -178.96(13) . . . . ? O1 C3 C17 N2 23(4) . . . . ? C18 C3 C17 N2 144(4) . . . . ? C2 C3 C17 N2 -88(4) . . . . ? O1 C3 C18 N3 69(3) . . . . ? C17 C3 C18 N3 -49(3) . . . . ? C2 C3 C18 N3 -18E1(10) . . . . ? O3 C4 N1 C10 -178.97(14) . . . . ? C2 C4 N1 C10 0.60(16) . . . . ? C8 C10 N1 C4 -178.79(14) . . . . ? C9 C10 N1 C4 1.68(17) . . . . ? C17 C3 O1 C1 -154.40(11) . . . . ? C18 C3 O1 C1 86.08(13) . . . . ? C2 C3 O1 C1 -34.95(12) . . . . ? O2 C1 O1 C3 19.17(13) . . . . ? C11 C1 O1 C3 -101.15(12) . . . . ? C9 C2 O2 C1 95.14(13) . . . . ? C4 C2 O2 C1 -149.41(11) . . . . ? C3 C2 O2 C1 -27.68(12) . . . . ? O1 C1 O2 C2 7.49(13) . . . . ? C11 C1 O2 C2 128.75(12) . . . . ? #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-06-11 at 15:11:03 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\progs\wingx\files\archive.dat # CIF files read : job struct data_10b _database_code_depnum_ccdc_archive 'CCDC 654063' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H8 Cl2 N3 O3, C3 H7 O1' _chemical_formula_sum 'C21 H15 Cl2 N3 O4' _chemical_formula_weight 444.26 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.2556(6) _cell_length_b 6.9193(3) _cell_length_c 22.4721(10) _cell_angle_alpha 90 _cell_angle_beta 95.608(2) _cell_angle_gamma 90 _cell_volume 2051.26(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9718 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27.5 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.35 _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.350 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.786 _exptl_absorpt_correction_T_max 0.885 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_unetI/netI 0.0188 _diffrn_reflns_number 31570 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4692 _reflns_number_gt 4579 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0264P)^2^+1.3432P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4692 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.036 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.433 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.83965(10) 1.27424(19) 0.52781(6) 0.0138(2) Uani 1 d . . . H1 H 0.9103 1.3206 0.5243 0.017 Uiso 1 calc R . . C2 C 0.85631(9) 1.11729(18) 0.61772(5) 0.0119(2) Uani 1 d . . . C3 C 0.83281(9) 0.96232(19) 0.56630(6) 0.0131(2) Uani 1 d . . . C4 C 0.97366(9) 1.13154(18) 0.63576(6) 0.0140(2) Uani 1 d . . . C5 C 0.71602(9) 1.08344(18) 0.69162(6) 0.0135(2) Uani 1 d . . . H5 H 0.6602 1.0911 0.6618 0.016 Uiso 1 calc R . . C6 C 0.70169(10) 1.06803(18) 0.75218(6) 0.0151(3) Uani 1 d . . . C7 C 0.78246(11) 1.05720(19) 0.79617(6) 0.0170(3) Uani 1 d . . . H7 H 0.7699 1.0451 0.8369 0.02 Uiso 1 calc R . . C8 C 0.88185(10) 1.06398(19) 0.78106(6) 0.0172(3) Uani 1 d . . . H8 H 0.9377 1.0585 0.8109 0.021 Uiso 1 calc R . . C9 C 0.81490(9) 1.08715(18) 0.67686(5) 0.0121(2) Uani 1 d . . . C10 C 0.89630(9) 1.07904(18) 0.72111(6) 0.0133(2) Uani 1 d . . . C11 C 0.76474(10) 1.39116(19) 0.48862(5) 0.0136(2) Uani 1 d . . . C12 C 0.79942(10) 1.54224(19) 0.45527(6) 0.0147(3) Uani 1 d . . . H12 H 0.8701 1.5664 0.4563 0.018 Uiso 1 calc R . . C13 C 0.73109(10) 1.6583(2) 0.42042(6) 0.0183(3) Uani 1 d . . . H13 H 0.7542 1.7632 0.3981 0.022 Uiso 1 calc R . . C14 C 0.62854(10) 1.6171(2) 0.41909(6) 0.0185(3) Uani 1 d . . . C15 C 0.59219(10) 1.4637(2) 0.45064(6) 0.0180(3) Uani 1 d . . . H15 H 0.5217 1.4361 0.448 0.022 Uiso 1 calc R . . C16 C 0.66108(10) 1.3516(2) 0.48604(6) 0.0170(3) Uani 1 d . . . H16 H 0.6376 1.2476 0.5086 0.02 Uiso 1 calc R . . C17 C 0.91107(10) 0.80777(19) 0.56772(6) 0.0149(3) Uani 1 d . . . C18 C 0.73152(10) 0.87027(19) 0.56950(6) 0.0155(3) Uani 1 d . . . N1 N 0.98835(8) 1.09766(17) 0.69556(5) 0.0151(2) Uani 1 d . . . HN1 H 1.0480(17) 1.099(3) 0.7162(10) 0.05 Uiso 1 d . . . N2 N 0.97055(9) 0.68827(18) 0.56931(5) 0.0214(3) Uani 1 d . . . N3 N 0.65286(9) 0.80458(19) 0.57113(6) 0.0235(3) Uani 1 d . . . O1 O 0.83030(7) 1.06923(13) 0.51287(4) 0.0167(2) Uani 1 d . . . O2 O 0.81599(7) 1.28556(13) 0.58821(4) 0.01305(18) Uani 1 d . . . O3 O 1.03707(7) 1.16547(15) 0.60175(4) 0.0202(2) Uani 1 d . . . Cl2 Cl 0.57862(3) 1.06819(5) 0.773166(15) 0.02056(9) Uani 1 d . . . Cl3 Cl 0.54243(3) 1.76279(6) 0.37600(2) 0.03464(11) Uani 1 d . . . C101 C 0.73033(11) 0.3275(2) 0.29870(6) 0.0216(3) Uani 1 d . . . C102 C 0.84231(11) 0.3596(3) 0.31013(7) 0.0306(4) Uani 1 d . . . H10A H 0.8771 0.2889 0.2803 0.046 Uiso 1 calc R . . H10B H 0.8661 0.3129 0.3502 0.046 Uiso 1 calc R . . H10C H 0.857 0.4979 0.3073 0.046 Uiso 1 calc R . . C103 C 0.68435(14) 0.1680(2) 0.33138(8) 0.0329(4) Uani 1 d . . . H10D H 0.6117 0.1601 0.3185 0.049 Uiso 1 calc R . . H10E H 0.6941 0.1934 0.3745 0.049 Uiso 1 calc R . . H10F H 0.717 0.0454 0.3227 0.049 Uiso 1 calc R . . O101 O 0.67948(8) 0.42822(19) 0.26296(5) 0.0351(3) Uani 1 d . . . 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 C1 0.0151(6) 0.0140(6) 0.0126(6) 0.0001(5) 0.0037(5) 0.0002(5) C2 0.0112(6) 0.0112(6) 0.0134(6) -0.0008(5) 0.0020(4) 0.0003(4) C3 0.0130(6) 0.0140(6) 0.0124(6) -0.0001(5) 0.0020(5) 0.0006(5) C4 0.0123(6) 0.0114(6) 0.0181(6) -0.0022(5) 0.0012(5) -0.0006(5) C5 0.0134(6) 0.0113(6) 0.0160(6) -0.0001(5) 0.0022(5) 0.0006(5) C6 0.0167(6) 0.0099(6) 0.0199(6) -0.0006(5) 0.0083(5) 0.0006(5) C7 0.0265(7) 0.0120(6) 0.0132(6) 0.0004(5) 0.0055(5) 0.0000(5) C8 0.0215(7) 0.0152(6) 0.0140(6) 0.0001(5) -0.0022(5) -0.0001(5) C9 0.0146(6) 0.0094(6) 0.0125(6) -0.0007(4) 0.0022(5) 0.0002(4) C10 0.0138(6) 0.0095(6) 0.0166(6) -0.0004(5) 0.0009(5) 0.0004(4) C11 0.0145(6) 0.0155(6) 0.0111(6) -0.0011(5) 0.0024(5) 0.0011(5) C12 0.0136(6) 0.0172(6) 0.0134(6) -0.0006(5) 0.0017(5) -0.0016(5) C13 0.0189(7) 0.0166(6) 0.0189(6) 0.0026(5) 0.0000(5) -0.0021(5) C14 0.0158(6) 0.0187(7) 0.0200(6) 0.0004(5) -0.0042(5) 0.0032(5) C15 0.0124(6) 0.0225(7) 0.0193(6) -0.0018(5) 0.0018(5) -0.0007(5) C16 0.0159(6) 0.0194(7) 0.0161(6) 0.0017(5) 0.0045(5) -0.0019(5) C17 0.0151(6) 0.0156(6) 0.0138(6) -0.0018(5) 0.0007(5) -0.0018(5) C18 0.0177(6) 0.0152(6) 0.0134(6) -0.0022(5) 0.0006(5) 0.0007(5) N1 0.0110(5) 0.0171(6) 0.0168(5) -0.0009(4) -0.0007(4) -0.0002(4) N2 0.0198(6) 0.0219(6) 0.0222(6) -0.0032(5) 0.0001(5) 0.0034(5) N3 0.0192(6) 0.0273(7) 0.0238(6) -0.0052(5) 0.0015(5) -0.0049(5) O1 0.0249(5) 0.0139(5) 0.0115(4) 0.0000(3) 0.0033(4) 0.0014(4) O2 0.0154(4) 0.0128(4) 0.0112(4) 0.0010(3) 0.0029(3) 0.0016(3) O3 0.0140(5) 0.0251(5) 0.0222(5) 0.0006(4) 0.0056(4) -0.0024(4) Cl2 0.02038(17) 0.01773(16) 0.02582(18) 0.00196(13) 0.01379(13) 0.00157(12) Cl3 0.02150(19) 0.0280(2) 0.0509(3) 0.01396(18) -0.01425(17) 0.00051(15) C101 0.0180(7) 0.0287(8) 0.0182(7) -0.0006(6) 0.0015(5) 0.0005(6) C102 0.0165(7) 0.0452(10) 0.0291(8) -0.0056(7) -0.0037(6) 0.0035(7) C103 0.0449(10) 0.0285(8) 0.0271(8) 0.0017(7) 0.0137(7) -0.0006(7) O101 0.0195(5) 0.0472(8) 0.0364(6) 0.0169(6) -0.0087(5) -0.0058(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O2 1.4248(15) . ? C1 O1 1.4601(15) . ? C1 C11 1.4984(17) . ? C1 H1 1 . ? C2 O2 1.4185(15) . ? C2 C9 1.5012(17) . ? C2 C4 1.5717(17) . ? C2 C3 1.5850(17) . ? C3 O1 1.4079(15) . ? C3 C17 1.4881(18) . ? C3 C18 1.4941(18) . ? C4 O3 1.2131(16) . ? C4 N1 1.3591(17) . ? C5 C9 1.3834(17) . ? C5 C6 1.3964(18) . ? C5 H5 0.95 . ? C6 C7 1.3864(19) . ? C6 Cl2 1.7420(13) . ? C7 C8 1.3931(19) . ? C7 H7 0.95 . ? C8 C10 1.3832(18) . ? C8 H8 0.95 . ? C9 C10 1.3951(17) . ? C10 N1 1.4043(17) . ? C11 C12 1.3904(18) . ? C11 C16 1.3967(18) . ? C12 C13 1.3928(18) . ? C12 H12 0.95 . ? C13 C14 1.3863(19) . ? C13 H13 0.95 . ? C14 C15 1.389(2) . ? C14 Cl3 1.7435(14) . ? C15 C16 1.3879(19) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 N2 1.1407(18) . ? C18 N3 1.1414(18) . ? N1 HN1 0.88(2) . ? C101 O101 1.2163(18) . ? C101 C103 1.489(2) . ? C101 C102 1.498(2) . ? C102 H10A 0.98 . ? C102 H10B 0.98 . ? C102 H10C 0.98 . ? C103 H10D 0.98 . ? C103 H10E 0.98 . ? C103 H10F 0.98 . ? 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 O2 C1 O1 104.53(10) . . ? O2 C1 C11 109.59(10) . . ? O1 C1 C11 110.67(10) . . ? O2 C1 H1 110.6 . . ? O1 C1 H1 110.6 . . ? C11 C1 H1 110.6 . . ? O2 C2 C9 111.99(10) . . ? O2 C2 C4 112.79(10) . . ? C9 C2 C4 102.63(10) . . ? O2 C2 C3 100.14(9) . . ? C9 C2 C3 119.25(10) . . ? C4 C2 C3 110.46(10) . . ? O1 C3 C17 110.75(10) . . ? O1 C3 C18 108.58(10) . . ? C17 C3 C18 108.69(11) . . ? O1 C3 C2 104.65(10) . . ? C17 C3 C2 112.55(10) . . ? C18 C3 C2 111.52(10) . . ? O3 C4 N1 127.96(12) . . ? O3 C4 C2 125.37(12) . . ? N1 C4 C2 106.67(10) . . ? C9 C5 C6 117.21(12) . . ? C9 C5 H5 121.4 . . ? C6 C5 H5 121.4 . . ? C7 C6 C5 122.00(12) . . ? C7 C6 Cl2 119.04(10) . . ? C5 C6 Cl2 118.94(10) . . ? C6 C7 C8 120.48(12) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C10 C8 C7 117.66(12) . . ? C10 C8 H8 121.2 . . ? C7 C8 H8 121.2 . . ? C5 C9 C10 120.89(12) . . ? C5 C9 C2 130.68(11) . . ? C10 C9 C2 108.20(11) . . ? C8 C10 C9 121.74(12) . . ? C8 C10 N1 127.86(12) . . ? C9 C10 N1 110.32(11) . . ? C12 C11 C16 120.05(12) . . ? C12 C11 C1 119.19(11) . . ? C16 C11 C1 120.76(12) . . ? C11 C12 C13 120.36(12) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 118.43(13) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C13 C14 C15 122.30(12) . . ? C13 C14 Cl3 118.72(11) . . ? C15 C14 Cl3 118.97(10) . . ? C16 C15 C14 118.57(12) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C11 120.25(12) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? N2 C17 C3 179.23(15) . . ? N3 C18 C3 178.00(15) . . ? C4 N1 C10 111.94(11) . . ? C4 N1 HN1 123.8(15) . . ? C10 N1 HN1 124.0(15) . . ? C3 O1 C1 108.66(9) . . ? C2 O2 C1 107.00(9) . . ? O101 C101 C103 121.56(14) . . ? O101 C101 C102 120.28(14) . . ? C103 C101 C102 118.15(14) . . ? C101 C102 H10A 109.5 . . ? C101 C102 H10B 109.5 . . ? H10A C102 H10B 109.5 . . ? C101 C102 H10C 109.5 . . ? H10A C102 H10C 109.5 . . ? H10B C102 H10C 109.5 . . ? C101 C103 H10D 109.5 . . ? C101 C103 H10E 109.5 . . ? H10D C103 H10E 109.5 . . ? C101 C103 H10F 109.5 . . ? H10D C103 H10F 109.5 . . ? H10E C103 H10F 109.5 . . ? 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 O2 C2 C3 O1 26.67(11) . . . . ? C9 C2 C3 O1 149.09(11) . . . . ? C4 C2 C3 O1 -92.46(11) . . . . ? O2 C2 C3 C17 147.00(10) . . . . ? C9 C2 C3 C17 -90.58(13) . . . . ? C4 C2 C3 C17 27.88(14) . . . . ? O2 C2 C3 C18 -90.53(11) . . . . ? C9 C2 C3 C18 31.88(15) . . . . ? C4 C2 C3 C18 150.34(11) . . . . ? O2 C2 C4 O3 -55.57(17) . . . . ? C9 C2 C4 O3 -176.25(13) . . . . ? C3 C2 C4 O3 55.57(17) . . . . ? O2 C2 C4 N1 124.78(11) . . . . ? C9 C2 C4 N1 4.10(13) . . . . ? C3 C2 C4 N1 -124.08(11) . . . . ? C9 C5 C6 C7 0.14(19) . . . . ? C9 C5 C6 Cl2 178.59(9) . . . . ? C5 C6 C7 C8 0.8(2) . . . . ? Cl2 C6 C7 C8 -177.61(10) . . . . ? C6 C7 C8 C10 -0.87(19) . . . . ? C6 C5 C9 C10 -1.06(18) . . . . ? C6 C5 C9 C2 -174.75(12) . . . . ? O2 C2 C9 C5 51.35(18) . . . . ? C4 C2 C9 C5 172.58(13) . . . . ? C3 C2 C9 C5 -65.00(18) . . . . ? O2 C2 C9 C10 -122.96(11) . . . . ? C4 C2 C9 C10 -1.72(13) . . . . ? C3 C2 C9 C10 120.70(12) . . . . ? C7 C8 C10 C9 -0.05(19) . . . . ? C7 C8 C10 N1 176.60(12) . . . . ? C5 C9 C10 C8 1.04(19) . . . . ? C2 C9 C10 C8 176.01(12) . . . . ? C5 C9 C10 N1 -176.14(11) . . . . ? C2 C9 C10 N1 -1.18(14) . . . . ? O2 C1 C11 C12 121.02(12) . . . . ? O1 C1 C11 C12 -124.23(12) . . . . ? O2 C1 C11 C16 -58.06(15) . . . . ? O1 C1 C11 C16 56.70(15) . . . . ? C16 C11 C12 C13 1.77(19) . . . . ? C1 C11 C12 C13 -177.31(12) . . . . ? C11 C12 C13 C14 -1.1(2) . . . . ? C12 C13 C14 C15 -0.7(2) . . . . ? C12 C13 C14 Cl3 179.54(10) . . . . ? C13 C14 C15 C16 1.9(2) . . . . ? Cl3 C14 C15 C16 -178.36(11) . . . . ? C14 C15 C16 C11 -1.3(2) . . . . ? C12 C11 C16 C15 -0.6(2) . . . . ? C1 C11 C16 C15 178.51(12) . . . . ? O1 C3 C17 N2 -162(14) . . . . ? C18 C3 C17 N2 -43(14) . . . . ? C2 C3 C17 N2 81(14) . . . . ? O1 C3 C18 N3 -35(4) . . . . ? C17 C3 C18 N3 -155(4) . . . . ? C2 C3 C18 N3 80(4) . . . . ? O3 C4 N1 C10 175.24(13) . . . . ? C2 C4 N1 C10 -5.12(14) . . . . ? C8 C10 N1 C4 -172.79(13) . . . . ? C9 C10 N1 C4 4.18(15) . . . . ? C17 C3 O1 C1 -127.27(11) . . . . ? C18 C3 O1 C1 113.46(11) . . . . ? C2 C3 O1 C1 -5.74(12) . . . . ? O2 C1 O1 C3 -17.49(12) . . . . ? C11 C1 O1 C3 -135.39(10) . . . . ? C9 C2 O2 C1 -165.84(10) . . . . ? C4 C2 O2 C1 78.98(12) . . . . ? C3 C2 O2 C1 -38.43(11) . . . . ? O1 C1 O2 C2 36.56(12) . . . . ? C11 C1 O2 C2 155.19(10) . . . . ? data_11a _database_code_depnum_ccdc_archive 'CCDC 654064' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H10 Cl1 N3 O3' _chemical_formula_sum 'C18 H10 Cl N3 O3' _chemical_formula_weight 351.74 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.4743(11) _cell_length_b 10.6042(12) _cell_length_c 13.0970(14) _cell_angle_alpha 90 _cell_angle_beta 98.668(5) _cell_angle_gamma 90 _cell_volume 1575.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8461 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 27.47 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.266 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.858 _exptl_absorpt_correction_T_max 0.961 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_unetI/netI 0.0316 _diffrn_reflns_number 15693 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3596 _reflns_number_gt 3325 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0332P)^2^+1.0054P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3596 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0873 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.368 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.054 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.46610(12) 0.21139(13) 0.63969(11) 0.0145(3) Uani 1 d . . . H1 H 0.5072 0.235 0.5803 0.017 Uiso 1 calc R . . C2 C 0.59863(11) 0.13187(12) 0.77724(10) 0.0126(3) Uani 1 d . . . C3 C 0.59728(11) 0.28156(12) 0.77284(10) 0.0136(3) Uani 1 d . . . C4 C 0.55183(12) 0.08726(12) 0.87750(10) 0.0141(3) Uani 1 d . . . C5 C 0.79927(12) 0.06278(13) 0.72107(11) 0.0170(3) Uani 1 d . . . H5 H 0.7817 0.0934 0.6523 0.02 Uiso 1 calc R . . C6 C 0.90760(12) 0.00517(13) 0.75699(12) 0.0187(3) Uani 1 d . . . H6 H 0.964 -0.0053 0.7115 0.022 Uiso 1 calc R . . C7 C 0.93348(12) -0.03682(13) 0.85831(12) 0.0199(3) Uani 1 d . . . H7 H 1.0085 -0.073 0.8815 0.024 Uiso 1 calc R . . C8 C 0.85190(12) -0.02712(13) 0.92704(11) 0.0173(3) Uani 1 d . . . H8 H 0.8699 -0.0554 0.9964 0.021 Uiso 1 calc R . . C9 C 0.71882(11) 0.07343(12) 0.78932(11) 0.0138(3) Uani 1 d . . . C10 C 0.74400(11) 0.02542(12) 0.88958(11) 0.0141(3) Uani 1 d . . . C11 C 0.33718(12) 0.19485(12) 0.60323(11) 0.0150(3) Uani 1 d . . . C12 C 0.29529(12) 0.19657(13) 0.49794(11) 0.0167(3) Uani 1 d . . . H12 H 0.3489 0.2065 0.4498 0.02 Uiso 1 calc R . . C13 C 0.17517(13) 0.18387(14) 0.46265(12) 0.0198(3) Uani 1 d . . . H13 H 0.146 0.1849 0.3908 0.024 Uiso 1 calc R . . C14 C 0.09914(12) 0.16966(13) 0.53461(12) 0.0198(3) Uani 1 d . . . C15 C 0.13960(13) 0.16538(14) 0.63990(12) 0.0204(3) Uani 1 d . . . H15 H 0.0858 0.1545 0.6877 0.024 Uiso 1 calc R . . C16 C 0.25951(12) 0.17723(13) 0.67451(12) 0.0181(3) Uani 1 d . . . H16 H 0.2886 0.1734 0.7463 0.022 Uiso 1 calc R . . C17 C 0.61295(12) 0.33929(12) 0.87698(11) 0.0158(3) Uani 1 d . . . C18 C 0.69135(12) 0.33246(13) 0.71619(11) 0.0163(3) Uani 1 d . . . N1 N 0.64384(10) 0.03619(11) 0.94004(9) 0.0144(2) Uani 1 d . . . HN1 H 0.6352(19) -0.001(2) 0.9986(18) 0.05 Uiso 1 d . . . N2 N 0.63247(12) 0.37613(12) 0.95976(10) 0.0231(3) Uani 1 d . . . N3 N 0.76022(11) 0.37477(13) 0.67170(11) 0.0241(3) Uani 1 d . . . O1 O 0.48442(8) 0.30783(9) 0.71822(7) 0.0148(2) Uani 1 d . . . O2 O 0.51819(8) 0.09948(9) 0.68868(7) 0.0153(2) Uani 1 d . . . O3 O 0.45053(8) 0.09902(9) 0.89364(8) 0.0177(2) Uani 1 d . . . Cl1 Cl -0.05211(3) 0.16213(4) 0.49145(3) 0.02768(12) Uani 1 d . . . 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 C1 0.0182(6) 0.0146(6) 0.0109(6) 0.0006(5) 0.0032(5) -0.0001(5) C2 0.0152(6) 0.0138(6) 0.0092(6) 0.0007(5) 0.0031(5) -0.0016(5) C3 0.0150(6) 0.0147(6) 0.0113(7) 0.0020(5) 0.0023(5) -0.0012(5) C4 0.0202(6) 0.0103(6) 0.0124(7) -0.0006(5) 0.0046(5) -0.0020(5) C5 0.0194(6) 0.0175(7) 0.0148(7) -0.0006(5) 0.0051(5) -0.0019(5) C6 0.0167(6) 0.0175(7) 0.0235(8) -0.0042(6) 0.0079(5) -0.0029(5) C7 0.0142(6) 0.0159(7) 0.0287(8) -0.0024(6) 0.0003(5) -0.0002(5) C8 0.0189(6) 0.0153(6) 0.0163(7) 0.0002(5) -0.0015(5) -0.0009(5) C9 0.0151(6) 0.0127(6) 0.0136(7) -0.0007(5) 0.0025(5) -0.0012(5) C10 0.0166(6) 0.0118(6) 0.0141(7) -0.0016(5) 0.0029(5) -0.0025(5) C11 0.0168(6) 0.0119(6) 0.0160(7) 0.0017(5) 0.0020(5) -0.0007(5) C12 0.0189(6) 0.0151(6) 0.0165(7) -0.0005(5) 0.0035(5) -0.0009(5) C13 0.0223(7) 0.0182(7) 0.0175(8) -0.0028(6) -0.0013(5) -0.0013(5) C14 0.0148(6) 0.0141(6) 0.0293(9) -0.0010(6) -0.0002(6) -0.0025(5) C15 0.0191(7) 0.0183(7) 0.0248(8) 0.0030(6) 0.0069(6) -0.0027(5) C16 0.0200(7) 0.0184(7) 0.0162(7) 0.0030(5) 0.0034(5) -0.0012(5) C17 0.0189(6) 0.0125(6) 0.0165(8) 0.0024(5) 0.0041(5) -0.0018(5) C18 0.0183(6) 0.0166(6) 0.0135(7) 0.0015(5) 0.0007(5) -0.0014(5) N1 0.0189(5) 0.0148(5) 0.0100(6) 0.0020(4) 0.0041(4) 0.0000(4) N2 0.0316(7) 0.0209(6) 0.0169(7) -0.0010(5) 0.0043(5) -0.0034(5) N3 0.0237(6) 0.0265(7) 0.0230(7) 0.0051(5) 0.0063(5) -0.0034(5) O1 0.0153(4) 0.0148(5) 0.0140(5) 0.0000(4) 0.0013(4) -0.0002(4) O2 0.0185(5) 0.0147(5) 0.0115(5) -0.0006(4) -0.0018(4) 0.0009(4) O3 0.0184(5) 0.0186(5) 0.0181(5) 0.0035(4) 0.0087(4) 0.0022(4) Cl1 0.01536(17) 0.0287(2) 0.0373(3) -0.00200(16) -0.00154(15) -0.00302(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O2 1.4358(16) . ? C1 O1 1.4431(16) . ? C1 C11 1.4947(18) . ? C1 H1 1 . ? C2 O2 1.4116(15) . ? C2 C9 1.4984(18) . ? C2 C4 1.5649(18) . ? C2 C3 1.5883(18) . ? C3 O1 1.4097(15) . ? C3 C17 1.4811(19) . ? C3 C18 1.4995(19) . ? C4 O3 1.2188(16) . ? C4 N1 1.3484(17) . ? C5 C9 1.3829(19) . ? C5 C6 1.4012(19) . ? C5 H5 0.95 . ? C6 C7 1.389(2) . ? C6 H6 0.95 . ? C7 C8 1.397(2) . ? C7 H7 0.95 . ? C8 C10 1.3787(18) . ? C8 H8 0.95 . ? C9 C10 1.3974(19) . ? C10 N1 1.4140(17) . ? C11 C12 1.390(2) . ? C11 C16 1.397(2) . ? C12 C13 1.3926(19) . ? C12 H12 0.95 . ? C13 C14 1.386(2) . ? C13 H13 0.95 . ? C14 C15 1.388(2) . ? C14 Cl1 1.7443(14) . ? C15 C16 1.3880(19) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 N2 1.1423(19) . ? C18 N3 1.1419(19) . ? N1 HN1 0.88(2) . ? 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 O2 C1 O1 105.14(10) . . ? O2 C1 C11 111.78(11) . . ? O1 C1 C11 109.98(11) . . ? O2 C1 H1 109.9 . . ? O1 C1 H1 109.9 . . ? C11 C1 H1 109.9 . . ? O2 C2 C9 117.62(11) . . ? O2 C2 C4 110.57(10) . . ? C9 C2 C4 102.30(10) . . ? O2 C2 C3 102.23(10) . . ? C9 C2 C3 114.90(11) . . ? C4 C2 C3 109.26(10) . . ? O1 C3 C17 111.12(11) . . ? O1 C3 C18 110.65(11) . . ? C17 C3 C18 108.08(11) . . ? O1 C3 C2 102.66(10) . . ? C17 C3 C2 112.37(11) . . ? C18 C3 C2 111.95(11) . . ? O3 C4 N1 128.00(13) . . ? O3 C4 C2 124.85(12) . . ? N1 C4 C2 107.15(11) . . ? C9 C5 C6 117.61(13) . . ? C9 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? C7 C6 C5 120.78(13) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 121.64(13) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C10 C8 C7 116.97(13) . . ? C10 C8 H8 121.5 . . ? C7 C8 H8 121.5 . . ? C5 C9 C10 120.93(12) . . ? C5 C9 C2 131.22(13) . . ? C10 C9 C2 107.85(11) . . ? C8 C10 C9 121.94(13) . . ? C8 C10 N1 128.02(13) . . ? C9 C10 N1 110.01(12) . . ? C12 C11 C16 120.30(13) . . ? C12 C11 C1 119.53(12) . . ? C16 C11 C1 120.17(13) . . ? C11 C12 C13 120.32(13) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 118.54(14) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C15 121.93(13) . . ? C13 C14 Cl1 118.83(12) . . ? C15 C14 Cl1 119.21(12) . . ? C14 C15 C16 119.22(14) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C11 119.65(14) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? N2 C17 C3 174.04(15) . . ? N3 C18 C3 177.45(15) . . ? C4 N1 C10 111.45(12) . . ? C4 N1 HN1 121.8(14) . . ? C10 N1 HN1 125.2(14) . . ? C3 O1 C1 104.21(10) . . ? C2 O2 C1 110.04(10) . . ? 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 O2 C2 C3 O1 26.66(12) . . . . ? C9 C2 C3 O1 155.23(11) . . . . ? C4 C2 C3 O1 -90.50(12) . . . . ? O2 C2 C3 C17 146.12(11) . . . . ? C9 C2 C3 C17 -85.31(14) . . . . ? C4 C2 C3 C17 28.96(14) . . . . ? O2 C2 C3 C18 -92.03(12) . . . . ? C9 C2 C3 C18 36.53(16) . . . . ? C4 C2 C3 C18 150.80(11) . . . . ? O2 C2 C4 O3 -43.65(17) . . . . ? C9 C2 C4 O3 -169.71(13) . . . . ? C3 C2 C4 O3 68.11(16) . . . . ? O2 C2 C4 N1 136.88(11) . . . . ? C9 C2 C4 N1 10.82(13) . . . . ? C3 C2 C4 N1 -111.36(12) . . . . ? C9 C5 C6 C7 -1.4(2) . . . . ? C5 C6 C7 C8 2.1(2) . . . . ? C6 C7 C8 C10 0.4(2) . . . . ? C6 C5 C9 C10 -1.6(2) . . . . ? C6 C5 C9 C2 178.12(13) . . . . ? O2 C2 C9 C5 48.8(2) . . . . ? C4 C2 C9 C5 170.14(14) . . . . ? C3 C2 C9 C5 -71.60(18) . . . . ? O2 C2 C9 C10 -131.45(12) . . . . ? C4 C2 C9 C10 -10.13(13) . . . . ? C3 C2 C9 C10 108.13(13) . . . . ? C7 C8 C10 C9 -3.5(2) . . . . ? C7 C8 C10 N1 174.24(13) . . . . ? C5 C9 C10 C8 4.2(2) . . . . ? C2 C9 C10 C8 -175.60(12) . . . . ? C5 C9 C10 N1 -173.91(12) . . . . ? C2 C9 C10 N1 6.33(15) . . . . ? O2 C1 C11 C12 -114.07(14) . . . . ? O1 C1 C11 C12 129.54(13) . . . . ? O2 C1 C11 C16 65.65(16) . . . . ? O1 C1 C11 C16 -50.74(16) . . . . ? C16 C11 C12 C13 1.6(2) . . . . ? C1 C11 C12 C13 -178.69(12) . . . . ? C11 C12 C13 C14 0.0(2) . . . . ? C12 C13 C14 C15 -1.3(2) . . . . ? C12 C13 C14 Cl1 176.63(11) . . . . ? C13 C14 C15 C16 0.8(2) . . . . ? Cl1 C14 C15 C16 -177.05(11) . . . . ? C14 C15 C16 C11 0.8(2) . . . . ? C12 C11 C16 C15 -2.0(2) . . . . ? C1 C11 C16 C15 178.27(13) . . . . ? O1 C3 C17 N2 157.1(14) . . . . ? C18 C3 C17 N2 -81.4(14) . . . . ? C2 C3 C17 N2 42.7(15) . . . . ? O1 C3 C18 N3 32(4) . . . . ? C17 C3 C18 N3 -90(4) . . . . ? C2 C3 C18 N3 146(4) . . . . ? O3 C4 N1 C10 172.86(13) . . . . ? C2 C4 N1 C10 -7.69(14) . . . . ? C8 C10 N1 C4 -176.82(13) . . . . ? C9 C10 N1 C4 1.10(15) . . . . ? C17 C3 O1 C1 -159.18(11) . . . . ? C18 C3 O1 C1 80.75(13) . . . . ? C2 C3 O1 C1 -38.86(12) . . . . ? O2 C1 O1 C3 37.44(12) . . . . ? C11 C1 O1 C3 157.93(11) . . . . ? C9 C2 O2 C1 -130.87(12) . . . . ? C4 C2 O2 C1 112.18(11) . . . . ? C3 C2 O2 C1 -4.04(13) . . . . ? O1 C1 O2 C2 -19.57(13) . . . . ? C11 C1 O2 C2 -138.86(11) . . . . ? data_7b _database_code_depnum_ccdc_archive 'CCDC 654065' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H15 Cl1 N2 O4' _chemical_formula_sum 'C20 H15 Cl N2 O4' _chemical_formula_weight 382.79 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.5421(6) _cell_length_b 26.3062(18) _cell_length_c 8.6602(6) _cell_angle_alpha 90 _cell_angle_beta 111.132(3) _cell_angle_gamma 90 _cell_volume 1815.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5576 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 27.45 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.23 _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 0.946 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_unetI/netI 0.0402 _diffrn_reflns_number 16325 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4140 _reflns_number_gt 3483 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0381P)^2^+0.8363P] 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_number_reflns 4140 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.332 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.051 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.68136(19) 0.36713(6) 0.39619(18) 0.0161(3) Uani 1 d . . . H1 H 0.7953 0.3592 0.4788 0.019 Uiso 1 calc R . . C2 C 0.52207(18) 0.36461(5) 0.55848(18) 0.0144(3) Uani 1 d . . . C3 C 0.46530(18) 0.31924(6) 0.42902(18) 0.0159(3) Uani 1 d . . . C4 C 0.69569(19) 0.39461(6) 0.25102(18) 0.0159(3) Uani 1 d . . . C5 C 0.85426(19) 0.40520(6) 0.24761(19) 0.0181(3) Uani 1 d . . . H5 H 0.9515 0.393 0.3338 0.022 Uiso 1 calc R . . C6 C 0.8711(2) 0.43349(6) 0.11905(19) 0.0199(3) Uani 1 d . . . H6 H 0.9788 0.4406 0.1156 0.024 Uiso 1 calc R . . C7 C 0.7272(2) 0.45109(6) -0.00396(18) 0.0190(3) Uani 1 d . . . C8 C 0.5677(2) 0.44016(6) -0.00452(19) 0.0198(3) Uani 1 d . . . H8 H 0.4707 0.452 -0.0918 0.024 Uiso 1 calc R . . C9 C 0.55253(19) 0.41187(6) 0.12384(19) 0.0191(3) Uani 1 d . . . H9 H 0.4444 0.4042 0.1254 0.023 Uiso 1 calc R . . C11 C 0.37908(18) 0.39123(6) 0.59250(17) 0.0146(3) Uani 1 d . . . C12 C 0.28114(19) 0.36482(6) 0.66450(19) 0.0187(3) Uani 1 d . . . H12 H 0.2998 0.3296 0.6876 0.022 Uiso 1 calc R . . C13 C 0.15640(19) 0.38989(7) 0.7026(2) 0.0218(3) Uani 1 d . . . H13 H 0.0903 0.3718 0.7519 0.026 Uiso 1 calc R . . C14 C 0.1285(2) 0.44137(7) 0.6684(2) 0.0232(4) Uani 1 d . . . H14 H 0.0449 0.4587 0.6965 0.028 Uiso 1 calc R . . C15 C 0.2231(2) 0.46749(6) 0.5931(2) 0.0217(3) Uani 1 d . . . H15 H 0.2023 0.5025 0.5676 0.026 Uiso 1 calc R . . C16 C 0.34849(19) 0.44250(6) 0.55457(18) 0.0177(3) Uani 1 d . . . H16 H 0.4126 0.4604 0.5027 0.021 Uiso 1 calc R . . C17 C 0.66537(18) 0.34832(6) 0.72218(18) 0.0156(3) Uani 1 d . . . C18 C 0.7346(2) 0.29917(6) 0.96783(18) 0.0196(3) Uani 1 d . . . H18A H 0.6794 0.2941 1.0495 0.023 Uiso 1 calc R . . H18B H 0.8228 0.3253 1.0117 0.023 Uiso 1 calc R . . C19 C 0.2929(2) 0.32862(6) 0.3061(2) 0.0223(3) Uani 1 d . . . C20 C 0.4669(2) 0.26783(6) 0.49952(19) 0.0200(3) Uani 1 d . . . C23 C 0.8128(2) 0.25009(7) 0.9432(2) 0.0280(4) Uani 1 d . . . H23A H 0.7251 0.2243 0.8992 0.042 Uiso 1 calc R . . H23B H 0.8939 0.2385 1.0495 0.042 Uiso 1 calc R . . H23C H 0.8702 0.2554 0.865 0.042 Uiso 1 calc R . . N1 N 0.1644(2) 0.33493(7) 0.2057(2) 0.0382(4) Uani 1 d . . . N2 N 0.4644(2) 0.22752(6) 0.5470(2) 0.0336(4) Uani 1 d . . . O1 O 0.58153(14) 0.32059(4) 0.34678(13) 0.0199(2) Uani 1 d . . . O2 O 0.58964(13) 0.39740(4) 0.46954(13) 0.0160(2) Uani 1 d . . . O3 O 0.80569(13) 0.36457(5) 0.76024(13) 0.0233(3) Uani 1 d . . . O4 O 0.61000(13) 0.31653(4) 0.80945(13) 0.0179(2) Uani 1 d . . . Cl1 Cl 0.74635(5) 0.488651(16) -0.16227(5) 0.02612(12) Uani 1 d . . . 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 C1 0.0158(7) 0.0148(7) 0.0184(7) -0.0024(6) 0.0071(6) 0.0004(6) C2 0.0151(7) 0.0125(7) 0.0168(7) -0.0005(5) 0.0072(6) -0.0019(6) C3 0.0155(7) 0.0152(7) 0.0172(7) -0.0013(6) 0.0061(6) -0.0004(6) C4 0.0193(8) 0.0145(7) 0.0158(7) -0.0047(6) 0.0087(6) -0.0003(6) C5 0.0162(7) 0.0190(8) 0.0177(7) -0.0036(6) 0.0047(6) 0.0020(6) C6 0.0173(8) 0.0215(8) 0.0230(8) -0.0041(6) 0.0097(6) -0.0028(6) C7 0.0254(8) 0.0184(8) 0.0150(7) -0.0019(6) 0.0096(6) -0.0022(6) C8 0.0184(8) 0.0225(8) 0.0160(7) -0.0012(6) 0.0031(6) 0.0011(6) C9 0.0154(7) 0.0219(8) 0.0210(8) -0.0026(6) 0.0079(6) -0.0015(6) C11 0.0129(7) 0.0163(7) 0.0130(7) -0.0023(5) 0.0027(6) 0.0014(6) C12 0.0158(7) 0.0193(8) 0.0199(8) 0.0018(6) 0.0052(6) 0.0005(6) C13 0.0140(7) 0.0301(9) 0.0215(8) -0.0008(7) 0.0067(6) -0.0002(6) C14 0.0153(8) 0.0309(9) 0.0214(8) -0.0065(7) 0.0042(6) 0.0081(7) C15 0.0207(8) 0.0179(8) 0.0224(8) -0.0024(6) 0.0028(6) 0.0054(6) C16 0.0183(7) 0.0168(8) 0.0161(7) -0.0007(6) 0.0039(6) 0.0002(6) C17 0.0155(7) 0.0153(7) 0.0174(7) -0.0038(6) 0.0077(6) 0.0016(6) C18 0.0200(8) 0.0235(8) 0.0135(7) 0.0014(6) 0.0040(6) 0.0025(6) C19 0.0214(8) 0.0238(9) 0.0204(8) -0.0062(6) 0.0058(7) 0.0025(7) C20 0.0191(8) 0.0187(8) 0.0199(8) -0.0034(6) 0.0043(6) -0.0034(6) C23 0.0308(9) 0.0285(9) 0.0241(8) 0.0056(7) 0.0091(7) 0.0119(8) N1 0.0257(8) 0.0499(11) 0.0299(8) -0.0127(7) -0.0012(7) 0.0115(7) N2 0.0419(9) 0.0197(8) 0.0332(8) -0.0011(6) 0.0066(7) -0.0064(7) O1 0.0231(6) 0.0158(5) 0.0257(6) -0.0049(4) 0.0147(5) -0.0020(4) O2 0.0192(5) 0.0134(5) 0.0192(5) -0.0015(4) 0.0117(4) -0.0009(4) O3 0.0156(6) 0.0345(7) 0.0199(6) 0.0000(5) 0.0064(4) -0.0043(5) O4 0.0158(5) 0.0177(6) 0.0183(5) 0.0030(4) 0.0037(4) 0.0003(4) Cl1 0.0287(2) 0.0278(2) 0.0232(2) 0.00477(16) 0.01109(17) -0.00417(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O2 1.4178(17) . ? C1 O1 1.4648(18) . ? C1 C4 1.493(2) . ? C1 H1 1 . ? C2 O2 1.4110(17) . ? C2 C11 1.526(2) . ? C2 C17 1.562(2) . ? C2 C3 1.589(2) . ? C3 O1 1.4156(18) . ? C3 C20 1.482(2) . ? C3 C19 1.494(2) . ? C4 C5 1.394(2) . ? C4 C9 1.394(2) . ? C5 C6 1.389(2) . ? C5 H5 0.95 . ? C6 C7 1.384(2) . ? C6 H6 0.95 . ? C7 C8 1.391(2) . ? C7 Cl1 1.7447(16) . ? C8 C9 1.382(2) . ? C8 H8 0.95 . ? C9 H9 0.95 . ? C11 C16 1.390(2) . ? C11 C12 1.396(2) . ? C12 C13 1.390(2) . ? C12 H12 0.95 . ? C13 C14 1.388(2) . ? C13 H13 0.95 . ? C14 C15 1.389(2) . ? C14 H14 0.95 . ? C15 C16 1.396(2) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 O3 1.2013(18) . ? C17 O4 1.3237(18) . ? C18 O4 1.4731(18) . ? C18 C23 1.504(2) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 N1 1.140(2) . ? C20 N2 1.141(2) . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? 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 O2 C1 O1 104.05(11) . . ? O2 C1 C4 109.36(12) . . ? O1 C1 C4 112.00(12) . . ? O2 C1 H1 110.4 . . ? O1 C1 H1 110.4 . . ? C4 C1 H1 110.4 . . ? O2 C2 C11 109.78(12) . . ? O2 C2 C17 108.79(11) . . ? C11 C2 C17 111.75(11) . . ? O2 C2 C3 98.90(11) . . ? C11 C2 C3 114.77(12) . . ? C17 C2 C3 111.98(12) . . ? O1 C3 C20 109.03(12) . . ? O1 C3 C19 109.09(12) . . ? C20 C3 C19 107.74(13) . . ? O1 C3 C2 104.19(11) . . ? C20 C3 C2 116.08(12) . . ? C19 C3 C2 110.52(12) . . ? C5 C4 C9 120.04(14) . . ? C5 C4 C1 119.34(14) . . ? C9 C4 C1 120.54(13) . . ? C6 C5 C4 120.42(14) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 118.46(14) . . ? C7 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C6 C7 C8 122.03(14) . . ? C6 C7 Cl1 119.06(12) . . ? C8 C7 Cl1 118.91(12) . . ? C9 C8 C7 118.96(14) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C4 120.06(14) . . ? C8 C9 H9 120 . . ? C4 C9 H9 120 . . ? C16 C11 C12 119.78(14) . . ? C16 C11 C2 119.65(13) . . ? C12 C11 C2 120.56(13) . . ? C13 C12 C11 120.27(15) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 119.98(15) . . ? C14 C13 H13 120 . . ? C12 C13 H13 120 . . ? C13 C14 C15 119.88(15) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 120.37(15) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C11 C16 C15 119.69(15) . . ? C11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? O3 C17 O4 126.49(14) . . ? O3 C17 C2 121.96(14) . . ? O4 C17 C2 111.53(12) . . ? O4 C18 C23 110.05(12) . . ? O4 C18 H18A 109.6 . . ? C23 C18 H18A 109.6 . . ? O4 C18 H18B 109.6 . . ? C23 C18 H18B 109.6 . . ? H18A C18 H18B 108.2 . . ? N1 C19 C3 176.29(17) . . ? N2 C20 C3 177.03(17) . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C3 O1 C1 108.30(11) . . ? C2 O2 C1 107.59(11) . . ? C17 O4 C18 116.14(12) . . ? 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 O2 C2 C3 O1 30.29(13) . . . . ? C11 C2 C3 O1 147.00(12) . . . . ? C17 C2 C3 O1 -84.22(14) . . . . ? O2 C2 C3 C20 150.17(12) . . . . ? C11 C2 C3 C20 -93.11(16) . . . . ? C17 C2 C3 C20 35.67(17) . . . . ? O2 C2 C3 C19 -86.77(14) . . . . ? C11 C2 C3 C19 29.95(17) . . . . ? C17 C2 C3 C19 158.73(12) . . . . ? O2 C1 C4 C5 121.77(14) . . . . ? O1 C1 C4 C5 -123.43(14) . . . . ? O2 C1 C4 C9 -54.97(18) . . . . ? O1 C1 C4 C9 59.83(18) . . . . ? C9 C4 C5 C6 0.8(2) . . . . ? C1 C4 C5 C6 -175.95(14) . . . . ? C4 C5 C6 C7 0.5(2) . . . . ? C5 C6 C7 C8 -1.7(2) . . . . ? C5 C6 C7 Cl1 177.65(12) . . . . ? C6 C7 C8 C9 1.6(2) . . . . ? Cl1 C7 C8 C9 -177.80(12) . . . . ? C7 C8 C9 C4 -0.2(2) . . . . ? C5 C4 C9 C8 -1.0(2) . . . . ? C1 C4 C9 C8 175.75(14) . . . . ? O2 C2 C11 C16 -7.74(18) . . . . ? C17 C2 C11 C16 113.06(15) . . . . ? C3 C2 C11 C16 -118.05(15) . . . . ? O2 C2 C11 C12 173.61(13) . . . . ? C17 C2 C11 C12 -65.59(17) . . . . ? C3 C2 C11 C12 63.30(18) . . . . ? C16 C11 C12 C13 -1.8(2) . . . . ? C2 C11 C12 C13 176.86(14) . . . . ? C11 C12 C13 C14 0.2(2) . . . . ? C12 C13 C14 C15 1.3(2) . . . . ? C13 C14 C15 C16 -1.3(2) . . . . ? C12 C11 C16 C15 1.8(2) . . . . ? C2 C11 C16 C15 -176.87(13) . . . . ? C14 C15 C16 C11 -0.2(2) . . . . ? O2 C2 C17 O3 2.83(19) . . . . ? C11 C2 C17 O3 -118.54(15) . . . . ? C3 C2 C17 O3 111.11(16) . . . . ? O2 C2 C17 O4 -178.62(11) . . . . ? C11 C2 C17 O4 60.00(16) . . . . ? C3 C2 C17 O4 -70.35(15) . . . . ? O1 C3 C19 N1 22(3) . . . . ? C20 C3 C19 N1 -96(3) . . . . ? C2 C3 C19 N1 136(3) . . . . ? O1 C3 C20 N2 -75(3) . . . . ? C19 C3 C20 N2 43(3) . . . . ? C2 C3 C20 N2 168(3) . . . . ? C20 C3 O1 C1 -133.86(12) . . . . ? C19 C3 O1 C1 108.72(13) . . . . ? C2 C3 O1 C1 -9.33(14) . . . . ? O2 C1 O1 C3 -15.26(14) . . . . ? C4 C1 O1 C3 -133.27(13) . . . . ? C11 C2 O2 C1 -161.78(11) . . . . ? C17 C2 O2 C1 75.65(13) . . . . ? C3 C2 O2 C1 -41.31(13) . . . . ? O1 C1 O2 C2 37.43(14) . . . . ? C4 C1 O2 C2 157.25(12) . . . . ? O3 C17 O4 C18 -0.8(2) . . . . ? C2 C17 O4 C18 -179.23(11) . . . . ? C23 C18 O4 C17 -92.86(16) . . . . ? #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-06-11 at 16:14:13 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\progs\wingx\files\archive.dat # CIF files read : job struct data_18b _database_code_depnum_ccdc_archive 'CCDC 654456' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H12 Cl1 N3 O4' _chemical_formula_sum 'C19 H12 Cl N3 O4' _chemical_formula_weight 381.77 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.1149(11) _cell_length_b 18.630(3) _cell_length_c 13.388(2) _cell_angle_alpha 90 _cell_angle_beta 98.387(6) _cell_angle_gamma 90 _cell_volume 1755.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3618 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.37 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.883 _exptl_absorpt_correction_T_max 0.951 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_unetI/netI 0.0439 _diffrn_reflns_number 18548 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.55 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 4026 _reflns_number_gt 3013 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1051P)^2^+2.5426P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4026 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0887 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.2032 _refine_ls_wR_factor_gt 0.1876 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.468 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.086 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4805(5) 0.01226(18) 0.7383(3) 0.0324(7) Uani 1 d . . . H1 H 0.5915 -0.0207 0.7382 0.039 Uiso 1 calc R . . C2 C 0.5714(4) 0.07535(14) 0.8821(2) 0.0197(6) Uani 1 d . . . C3 C 0.5918(4) 0.12578(15) 0.7884(2) 0.0201(6) Uani 1 d . . . C4 C 0.7667(4) 0.04111(15) 0.9239(2) 0.0221(6) Uani 1 d . . . C5 C 0.3500(4) 0.14334(15) 0.9886(2) 0.0225(6) Uani 1 d . . . H5 H 0.2427 0.1447 0.9372 0.027 Uiso 1 calc R . . C6 C 0.3454(4) 0.17358(16) 1.0827(2) 0.0267(6) Uani 1 d . . . C7 C 0.5018(4) 0.17310(16) 1.1575(2) 0.0257(6) Uani 1 d . . . H7 H 0.4944 0.1959 1.2203 0.031 Uiso 1 calc R . . C8 C 0.6687(4) 0.13972(15) 1.1417(2) 0.0234(6) Uani 1 d . . . H8 H 0.7767 0.1388 1.1926 0.028 Uiso 1 calc R . . C9 C 0.5174(4) 0.11132(14) 0.9730(2) 0.0198(6) Uani 1 d . . . C10 C 0.6719(4) 0.10814(14) 1.0496(2) 0.0202(6) Uani 1 d . . . C11 C 0.3052(5) -0.01681(18) 0.6746(2) 0.0315(7) Uani 1 d . . . C12 C 0.1277(5) 0.0053(2) 0.6852(3) 0.0384(8) Uani 1 d . . . H12 H 0.1122 0.044 0.7295 0.046 Uiso 1 calc R . . C13 C -0.0256(5) -0.0261(2) 0.6345(3) 0.0430(9) Uani 1 d . . . H13 H -0.1482 -0.0085 0.6418 0.052 Uiso 1 calc R . . C14 C -0.0100(5) -0.08237(19) 0.5734(3) 0.0370(8) Uani 1 d . . . C15 C 0.1649(6) -0.10743(18) 0.5557(3) 0.0408(9) Uani 1 d . . . H15 H 0.1758 -0.1457 0.5101 0.049 Uiso 1 calc R . . C16 C 0.3302(5) -0.0727(2) 0.6099(3) 0.0387(8) Uani 1 d . . . H16 H 0.4542 -0.088 0.6013 0.046 Uiso 1 calc R . . C17 C -0.1661(5) -0.1749(2) 0.4648(3) 0.0462(9) Uani 1 d . . . H17A H -0.1153 -0.1612 0.4033 0.069 Uiso 1 calc R . . H17B H -0.2932 -0.1954 0.4466 0.069 Uiso 1 calc R . . H17C H -0.0822 -0.2105 0.5022 0.069 Uiso 1 calc R . . C18 C 0.4739(4) 0.19107(16) 0.7896(2) 0.0237(6) Uani 1 d . . . C19 C 0.7903(4) 0.14792(16) 0.7863(2) 0.0242(6) Uani 1 d . . . N1 N 0.8175(3) 0.06684(13) 1.01727(19) 0.0223(5) Uani 1 d . . . HN1 H 0.908(6) 0.053(2) 1.051(3) 0.05 Uiso 1 d . . . N2 N 0.3823(4) 0.24086(16) 0.7922(2) 0.0362(7) Uani 1 d . . . N3 N 0.9444(4) 0.16431(16) 0.7884(2) 0.0356(7) Uani 1 d . . . O1 O 0.5218(3) 0.08456(12) 0.70332(15) 0.0305(5) Uani 1 d . . . O2 O 0.4405(3) 0.02443(10) 0.83711(14) 0.0219(4) Uani 1 d . . . O3 O 0.8522(3) -0.00107(12) 0.87770(15) 0.0273(5) Uani 1 d . . . O4 O -0.1770(4) -0.11302(16) 0.5262(2) 0.0497(7) Uani 1 d . . . Cl1 Cl 0.13552(10) 0.21292(5) 1.10636(7) 0.0415(3) Uani 1 d . . . 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 C1 0.0306(15) 0.0317(17) 0.0359(18) -0.0023(13) 0.0084(13) -0.0001(12) C2 0.0200(12) 0.0171(13) 0.0229(14) -0.0004(10) 0.0056(10) -0.0005(10) C3 0.0184(12) 0.0211(14) 0.0212(14) 0.0003(10) 0.0037(10) -0.0014(10) C4 0.0243(13) 0.0190(14) 0.0239(14) 0.0026(11) 0.0061(11) 0.0027(10) C5 0.0178(12) 0.0228(14) 0.0272(15) -0.0020(11) 0.0042(11) -0.0018(10) C6 0.0211(13) 0.0257(15) 0.0352(17) -0.0061(12) 0.0101(12) -0.0007(11) C7 0.0276(14) 0.0240(15) 0.0268(15) -0.0070(11) 0.0078(11) -0.0025(11) C8 0.0236(13) 0.0213(14) 0.0252(15) -0.0019(11) 0.0035(11) -0.0022(10) C9 0.0222(13) 0.0164(13) 0.0215(14) 0.0001(10) 0.0062(10) -0.0020(10) C10 0.0208(12) 0.0153(13) 0.0250(14) 0.0001(10) 0.0049(10) 0.0006(10) C11 0.0368(16) 0.0321(17) 0.0260(16) -0.0026(13) 0.0060(13) -0.0116(13) C12 0.0408(18) 0.0378(19) 0.0389(19) -0.0020(15) 0.0138(15) 0.0076(15) C13 0.0402(19) 0.047(2) 0.044(2) 0.0004(17) 0.0136(16) 0.0054(16) C14 0.0306(16) 0.0360(19) 0.042(2) 0.0088(15) -0.0032(14) -0.0074(13) C15 0.072(3) 0.0235(17) 0.0269(17) -0.0076(13) 0.0055(16) 0.0071(16) C16 0.0317(16) 0.050(2) 0.0355(19) 0.0037(15) 0.0096(14) 0.0153(15) C17 0.045(2) 0.043(2) 0.046(2) -0.0140(17) -0.0086(16) -0.0075(16) C18 0.0195(12) 0.0275(15) 0.0246(15) 0.0088(11) 0.0054(11) 0.0025(11) C19 0.0228(13) 0.0235(15) 0.0272(15) 0.0029(11) 0.0064(11) 0.0027(11) N1 0.0217(11) 0.0220(13) 0.0230(12) -0.0001(9) 0.0023(9) 0.0052(9) N2 0.0313(14) 0.0389(16) 0.0408(17) 0.0158(13) 0.0128(12) 0.0105(12) N3 0.0225(12) 0.0363(16) 0.0490(18) 0.0110(13) 0.0082(12) 0.0009(11) O1 0.0408(12) 0.0308(12) 0.0201(11) -0.0010(8) 0.0049(9) -0.0137(9) O2 0.0251(10) 0.0198(10) 0.0212(10) -0.0025(7) 0.0051(8) -0.0044(7) O3 0.0300(11) 0.0282(11) 0.0240(11) -0.0021(8) 0.0049(8) 0.0110(8) O4 0.0409(14) 0.0544(18) 0.0512(17) -0.0090(13) -0.0017(12) -0.0071(12) Cl1 0.0223(4) 0.0554(6) 0.0483(5) -0.0230(4) 0.0108(3) 0.0028(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O2 1.411(4) . ? C1 O1 1.470(4) . ? C1 C11 1.506(4) . ? C1 H1 1 . ? C2 O2 1.402(3) . ? C2 C9 1.488(4) . ? C2 C4 1.557(4) . ? C2 C3 1.590(4) . ? C3 O1 1.404(3) . ? C3 C19 1.476(4) . ? C3 C18 1.479(4) . ? C4 O3 1.217(3) . ? C4 N1 1.338(4) . ? C5 C9 1.375(4) . ? C5 C6 1.385(4) . ? C5 H5 0.95 . ? C6 C7 1.385(4) . ? C6 Cl1 1.734(3) . ? C7 C8 1.384(4) . ? C7 H7 0.95 . ? C8 C10 1.370(4) . ? C8 H8 0.95 . ? C9 C10 1.390(4) . ? C10 N1 1.409(3) . ? C11 C12 1.356(5) . ? C11 C16 1.382(5) . ? C12 C13 1.333(5) . ? C12 H12 0.95 . ? C13 C14 1.344(5) . ? C13 H13 0.95 . ? C14 C15 1.381(5) . ? C14 O4 1.384(4) . ? C15 C16 1.442(5) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 O4 1.425(5) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? C18 N2 1.137(4) . ? C19 N3 1.134(4) . ? N1 HN1 0.77(4) . ? 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 O2 C1 O1 103.2(2) . . ? O2 C1 C11 109.0(3) . . ? O1 C1 C11 109.6(3) . . ? O2 C1 H1 111.6 . . ? O1 C1 H1 111.6 . . ? C11 C1 H1 111.6 . . ? O2 C2 C9 114.9(2) . . ? O2 C2 C4 112.3(2) . . ? C9 C2 C4 102.3(2) . . ? O2 C2 C3 101.1(2) . . ? C9 C2 C3 116.3(2) . . ? C4 C2 C3 110.2(2) . . ? O1 C3 C19 111.4(2) . . ? O1 C3 C18 108.9(2) . . ? C19 C3 C18 108.5(2) . . ? O1 C3 C2 104.7(2) . . ? C19 C3 C2 112.2(2) . . ? C18 C3 C2 111.1(2) . . ? O3 C4 N1 128.2(3) . . ? O3 C4 C2 124.6(3) . . ? N1 C4 C2 107.1(2) . . ? C9 C5 C6 116.8(3) . . ? C9 C5 H5 121.6 . . ? C6 C5 H5 121.6 . . ? C7 C6 C5 122.2(3) . . ? C7 C6 Cl1 119.5(2) . . ? C5 C6 Cl1 118.3(2) . . ? C8 C7 C6 120.6(3) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C10 C8 C7 117.3(3) . . ? C10 C8 H8 121.4 . . ? C7 C8 H8 121.4 . . ? C5 C9 C10 121.1(3) . . ? C5 C9 C2 130.7(3) . . ? C10 C9 C2 108.3(2) . . ? C8 C10 C9 122.0(3) . . ? C8 C10 N1 128.4(3) . . ? C9 C10 N1 109.6(2) . . ? C12 C11 C16 120.1(3) . . ? C12 C11 C1 122.6(3) . . ? C16 C11 C1 117.0(3) . . ? C13 C12 C11 121.3(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 121.2(3) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C13 C14 C15 121.6(3) . . ? C13 C14 O4 117.2(3) . . ? C15 C14 O4 121.2(3) . . ? C14 C15 C16 116.8(3) . . ? C14 C15 H15 121.6 . . ? C16 C15 H15 121.6 . . ? C11 C16 C15 118.9(3) . . ? C11 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N2 C18 C3 178.8(3) . . ? N3 C19 C3 177.4(3) . . ? C4 N1 C10 111.8(2) . . ? C4 N1 HN1 121(3) . . ? C10 N1 HN1 126(3) . . ? C3 O1 C1 107.8(2) . . ? C2 O2 C1 107.4(2) . . ? C14 O4 C17 118.8(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 O2 C2 C3 O1 -18.0(2) . . . . ? C9 C2 C3 O1 -143.2(2) . . . . ? C4 C2 C3 O1 100.9(2) . . . . ? O2 C2 C3 C19 -139.0(2) . . . . ? C9 C2 C3 C19 95.8(3) . . . . ? C4 C2 C3 C19 -20.0(3) . . . . ? O2 C2 C3 C18 99.4(2) . . . . ? C9 C2 C3 C18 -25.8(3) . . . . ? C4 C2 C3 C18 -141.6(2) . . . . ? O2 C2 C4 O3 46.9(4) . . . . ? C9 C2 C4 O3 170.6(3) . . . . ? C3 C2 C4 O3 -65.0(3) . . . . ? O2 C2 C4 N1 -133.1(2) . . . . ? C9 C2 C4 N1 -9.3(3) . . . . ? C3 C2 C4 N1 115.0(2) . . . . ? C9 C5 C6 C7 1.1(4) . . . . ? C9 C5 C6 Cl1 -178.7(2) . . . . ? C5 C6 C7 C8 -2.2(5) . . . . ? Cl1 C6 C7 C8 177.6(2) . . . . ? C6 C7 C8 C10 0.4(4) . . . . ? C6 C5 C9 C10 1.7(4) . . . . ? C6 C5 C9 C2 -178.9(3) . . . . ? O2 C2 C9 C5 -48.9(4) . . . . ? C4 C2 C9 C5 -170.9(3) . . . . ? C3 C2 C9 C5 68.9(4) . . . . ? O2 C2 C9 C10 130.5(2) . . . . ? C4 C2 C9 C10 8.5(3) . . . . ? C3 C2 C9 C10 -111.7(3) . . . . ? C7 C8 C10 C9 2.4(4) . . . . ? C7 C8 C10 N1 -175.1(3) . . . . ? C5 C9 C10 C8 -3.5(4) . . . . ? C2 C9 C10 C8 177.0(3) . . . . ? C5 C9 C10 N1 174.4(2) . . . . ? C2 C9 C10 N1 -5.1(3) . . . . ? O2 C1 C11 C12 36.4(4) . . . . ? O1 C1 C11 C12 -75.9(4) . . . . ? O2 C1 C11 C16 -137.6(3) . . . . ? O1 C1 C11 C16 110.1(3) . . . . ? C16 C11 C12 C13 0.3(5) . . . . ? C1 C11 C12 C13 -173.5(3) . . . . ? C11 C12 C13 C14 2.0(6) . . . . ? C12 C13 C14 C15 -3.8(6) . . . . ? C12 C13 C14 O4 178.0(3) . . . . ? C13 C14 C15 C16 3.0(5) . . . . ? O4 C14 C15 C16 -178.9(3) . . . . ? C12 C11 C16 C15 -1.0(5) . . . . ? C1 C11 C16 C15 173.2(3) . . . . ? C14 C15 C16 C11 -0.6(5) . . . . ? O1 C3 C18 N2 118(16) . . . . ? C19 C3 C18 N2 -120(16) . . . . ? C2 C3 C18 N2 3(16) . . . . ? O1 C3 C19 N3 -137(7) . . . . ? C18 C3 C19 N3 104(7) . . . . ? C2 C3 C19 N3 -20(7) . . . . ? O3 C4 N1 C10 -173.1(3) . . . . ? C2 C4 N1 C10 6.8(3) . . . . ? C8 C10 N1 C4 176.4(3) . . . . ? C9 C10 N1 C4 -1.3(3) . . . . ? C19 C3 O1 C1 115.9(3) . . . . ? C18 C3 O1 C1 -124.6(2) . . . . ? C2 C3 O1 C1 -5.7(3) . . . . ? O2 C1 O1 C3 27.5(3) . . . . ? C11 C1 O1 C3 143.5(3) . . . . ? C9 C2 O2 C1 162.3(2) . . . . ? C4 C2 O2 C1 -81.3(3) . . . . ? C3 C2 O2 C1 36.2(3) . . . . ? O1 C1 O2 C2 -40.9(3) . . . . ? C11 C1 O2 C2 -157.4(2) . . . . ? C13 C14 O4 C17 -177.0(3) . . . . ? C15 C14 O4 C17 4.8(5) . . . . ?