# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email bernard.tinant@uclouvain.be _publ_contact_author_name 'Bernard Tinant' loop_ _publ_author_name 'Francois Robert' 'Pierre-Loic Jacquemin' 'Bernard Tinant' 'Yann Garcia' data_plj10or3 _database_code_depnum_ccdc_archive 'CCDC 854915' #TrackingRef 'plj10or3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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/n ' 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 9.863(3) _cell_length_b 10.363(3) _cell_length_c 11.563(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.28(2) _cell_angle_gamma 90.00 _cell_volume 1085.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 3. _cell_measurement_theta_max 26.3 _exptl_crystal_description bloc _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.084 _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 125(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'RU200 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '65 images, \D\F 3\%' _diffrn_detector_area_resol_mean 6.66 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8564 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2120 _reflns_number_gt 1931 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement MAR _computing_data_reduction MARHKL _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The data were not corrected for absorption but the collection mode take at least partially the absorption phenomena into account (see the total number of images and collected reflexions vs the number of independent reflexions). The H atoms were refined with a common isotropic temperature parameter. (U~eq~ = 0.049 \%A^2^) 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^)+(0.0483P)^2^+0.4784P] 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 refxyz _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.152(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2120 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1263 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _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 0.04944(16) 0.37631(13) 0.83070(14) 0.0290(4) Uani 1 1 d . . . C2 C 0.14609(17) 0.35028(13) 0.77056(13) 0.0291(4) Uani 1 1 d . . . C3 C 0.25721(17) 0.25911(14) 0.82142(14) 0.0319(4) Uani 1 1 d . . . C4 C 0.27417(19) 0.19526(14) 0.93150(15) 0.0346(4) Uani 1 1 d . . . C5 C 0.17998(19) 0.21998(15) 0.99197(15) 0.0353(4) Uani 1 1 d . . . C6 C 0.06857(18) 0.30952(14) 0.94152(15) 0.0326(4) Uani 1 1 d . . . C7 C -0.06753(18) 0.47214(14) 0.78049(16) 0.0351(4) Uani 1 1 d . . . N8 N -0.08519(16) 0.53806(12) 0.68212(14) 0.0408(4) Uani 1 1 d . . . C9 C -0.2060(2) 0.63103(17) 0.6371(2) 0.0542(6) Uani 1 1 d . . . C10 C -0.14934(16) 0.76762(14) 0.64767(14) 0.0303(4) Uani 1 1 d . . . N11 N -0.06934(15) 0.80984(13) 0.76401(12) 0.0353(4) Uani 1 1 d . . . C12 C -0.01977(19) 0.93059(16) 0.77590(17) 0.0415(4) Uani 1 1 d . . . C13 C -0.0467(2) 1.01336(16) 0.6769(2) 0.0467(5) Uani 1 1 d . . . C14 C -0.1288(2) 0.96934(17) 0.55766(18) 0.0438(5) Uani 1 1 d . . . C15 C -0.18126(18) 0.84359(16) 0.54189(15) 0.0359(4) Uani 1 1 d . . . O16 O 0.13413(15) 0.41256(11) 0.66419(11) 0.0414(3) Uani 1 1 d . . . H3 H 0.324(2) 0.246(2) 0.7810(19) 0.0489(16) Uiso 1 1 d . . . H4 H 0.358(2) 0.133(2) 0.9680(19) 0.0489(16) Uiso 1 1 d . . . H5 H 0.196(2) 0.173(2) 1.0713(19) 0.0489(16) Uiso 1 1 d . . . H6 H 0.000(2) 0.3274(19) 0.9927(19) 0.0489(16) Uiso 1 1 d . . . H7 H -0.131(2) 0.483(2) 0.8281(19) 0.0489(16) Uiso 1 1 d . . . H9A H -0.267(2) 0.625(2) 0.683(2) 0.0489(16) Uiso 1 1 d . . . H9B H -0.271(3) 0.614(2) 0.547(2) 0.0489(16) Uiso 1 1 d . . . H12 H 0.046(2) 0.963(2) 0.8636(19) 0.0489(16) Uiso 1 1 d . . . H13 H -0.006(2) 1.102(2) 0.6937(18) 0.0489(16) Uiso 1 1 d . . . H14 H -0.151(2) 1.024(2) 0.4863(19) 0.0489(16) Uiso 1 1 d . . . H15 H -0.241(2) 0.807(2) 0.462(2) 0.0489(16) Uiso 1 1 d . . . H16 H 0.057(3) 0.475(2) 0.6468(19) 0.0489(16) Uiso 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 0.0290(8) 0.0224(7) 0.0342(8) -0.0042(5) 0.0110(6) -0.0050(5) C2 0.0350(8) 0.0230(7) 0.0291(7) -0.0033(5) 0.0124(6) -0.0068(5) C3 0.0346(9) 0.0288(7) 0.0357(8) -0.0063(6) 0.0174(7) -0.0031(6) C4 0.0371(9) 0.0275(7) 0.0361(8) -0.0025(6) 0.0111(7) 0.0017(6) C5 0.0436(10) 0.0305(8) 0.0321(8) 0.0018(6) 0.0152(7) -0.0023(6) C6 0.0353(9) 0.0305(8) 0.0367(8) -0.0049(6) 0.0190(7) -0.0055(6) C7 0.0290(9) 0.0244(7) 0.0494(9) -0.0046(6) 0.0129(7) -0.0057(6) N8 0.0360(8) 0.0231(7) 0.0532(8) 0.0016(6) 0.0069(6) -0.0022(5) C9 0.0330(11) 0.0294(9) 0.0824(15) 0.0081(9) 0.0038(10) -0.0016(7) C10 0.0254(8) 0.0267(7) 0.0368(8) 0.0019(6) 0.0100(6) 0.0023(5) N11 0.0342(8) 0.0400(7) 0.0320(7) 0.0023(5) 0.0133(6) 0.0021(5) C12 0.0343(10) 0.0386(9) 0.0460(9) -0.0123(7) 0.0098(7) 0.0019(7) C13 0.0314(10) 0.0262(8) 0.0787(13) 0.0016(8) 0.0179(9) 0.0003(6) C14 0.0365(10) 0.0440(10) 0.0574(11) 0.0262(8) 0.0255(8) 0.0128(7) C15 0.0327(9) 0.0424(9) 0.0309(8) 0.0020(6) 0.0108(7) 0.0092(6) O16 0.0517(8) 0.0375(7) 0.0381(6) 0.0061(5) 0.0210(6) -0.0012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.402(2) . ? C1 C2 1.410(2) . ? C1 C7 1.458(2) . ? C2 O16 1.3522(18) . ? C2 C3 1.389(2) . ? C3 C4 1.385(2) . ? C3 H3 0.96(2) . ? C4 C5 1.390(2) . ? C4 H4 1.00(2) . ? C5 C6 1.379(2) . ? C5 H5 1.00(2) . ? C6 H6 1.08(2) . ? C7 N8 1.278(2) . ? C7 H7 0.99(2) . ? N8 C9 1.459(2) . ? C9 C10 1.509(2) . ? C9 H9A 0.95(2) . ? C9 H9B 1.00(2) . ? C10 N11 1.336(2) . ? C10 C15 1.382(2) . ? N11 C12 1.331(2) . ? C12 C13 1.370(3) . ? C12 H12 1.02(2) . ? C13 C14 1.372(3) . ? C13 H13 0.99(2) . ? C14 C15 1.387(3) . ? C14 H14 0.96(2) . ? C15 H15 0.96(2) . ? O16 H16 0.95(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 C6 C1 C2 118.89(14) . . ? C6 C1 C7 119.99(14) . . ? C2 C1 C7 121.11(14) . . ? O16 C2 C3 118.70(14) . . ? O16 C2 C1 121.61(14) . . ? C3 C2 C1 119.68(14) . . ? C4 C3 C2 120.17(14) . . ? C4 C3 H3 121.5(12) . . ? C2 C3 H3 118.2(12) . . ? C3 C4 C5 120.83(15) . . ? C3 C4 H4 118.3(12) . . ? C5 C4 H4 120.9(12) . . ? C6 C5 C4 119.38(14) . . ? C6 C5 H5 122.1(12) . . ? C4 C5 H5 118.5(12) . . ? C5 C6 C1 121.04(14) . . ? C5 C6 H6 116.9(11) . . ? C1 C6 H6 122.0(11) . . ? N8 C7 C1 121.77(15) . . ? N8 C7 H7 122.8(12) . . ? C1 C7 H7 115.4(12) . . ? C7 N8 C9 118.38(17) . . ? N8 C9 C10 111.51(15) . . ? N8 C9 H9A 111.2(13) . . ? C10 C9 H9A 108.3(13) . . ? N8 C9 H9B 110.7(12) . . ? C10 C9 H9B 108.1(12) . . ? H9A C9 H9B 106.9(18) . . ? N11 C10 C15 122.81(14) . . ? N11 C10 C9 116.19(15) . . ? C15 C10 C9 121.00(16) . . ? C12 N11 C10 117.30(14) . . ? N11 C12 C13 124.09(16) . . ? N11 C12 H12 118.5(12) . . ? C13 C12 H12 117.4(12) . . ? C12 C13 C14 118.30(16) . . ? C12 C13 H13 119.1(12) . . ? C14 C13 H13 122.6(12) . . ? C13 C14 C15 119.06(15) . . ? C13 C14 H14 120.8(13) . . ? C15 C14 H14 120.1(13) . . ? C10 C15 C14 118.42(16) . . ? C10 C15 H15 117.7(13) . . ? C14 C15 H15 123.9(12) . . ? C2 O16 H16 106.9(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 C6 C1 C2 O16 -179.30(13) . . . . ? C7 C1 C2 O16 -0.2(2) . . . . ? C6 C1 C2 C3 0.3(2) . . . . ? C7 C1 C2 C3 179.47(13) . . . . ? O16 C2 C3 C4 178.84(13) . . . . ? C1 C2 C3 C4 -0.8(2) . . . . ? C2 C3 C4 C5 0.7(2) . . . . ? C3 C4 C5 C6 -0.2(2) . . . . ? C4 C5 C6 C1 -0.3(2) . . . . ? C2 C1 C6 C5 0.2(2) . . . . ? C7 C1 C6 C5 -178.91(14) . . . . ? C6 C1 C7 N8 177.59(14) . . . . ? C2 C1 C7 N8 -1.5(2) . . . . ? C1 C7 N8 C9 179.31(14) . . . . ? C7 N8 C9 C10 114.47(19) . . . . ? N8 C9 C10 N11 -63.0(2) . . . . ? N8 C9 C10 C15 117.76(19) . . . . ? C15 C10 N11 C12 0.1(2) . . . . ? C9 C10 N11 C12 -179.15(15) . . . . ? C10 N11 C12 C13 0.5(3) . . . . ? N11 C12 C13 C14 -0.6(3) . . . . ? C12 C13 C14 C15 0.1(3) . . . . ? N11 C10 C15 C14 -0.5(2) . . . . ? C9 C10 C15 C14 178.63(16) . . . . ? C13 C14 C15 C10 0.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.353 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.048 # Attachment 'plj14or1.cif' data_plj14or1 _database_code_depnum_ccdc_archive 'CCDC 854916' #TrackingRef 'plj14or1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 Cl N2 O' _chemical_formula_weight 246.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M ' P21/c ' 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 13.864(4) _cell_length_b 6.004(2) _cell_length_c 14.041(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.95(2) _cell_angle_gamma 90.00 _cell_volume 1134.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 3. _cell_measurement_theta_max 26.4 _exptl_crystal_description platelike _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.320 _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 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'RU200 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '143 images, \D\F 3\%' _diffrn_detector_area_resol_mean 6.66 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19898 _diffrn_reflns_av_R_equivalents 0.053 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 26.39 _reflns_number_total 2257 _reflns_number_gt 2167 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement MAR _computing_data_reduction MARHKL _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The data were not corrected for absorption but the collection mode take at least partially the absorption phenomena into account (see the total number of images and collected reflexions vs the number of independent reflexions). The H atoms were refined with a common isotropic temperature parameter. (U~eq~ = 0.028 \%A^2^) 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^)+(0.0524P)^2^+0.8238P] 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 refxyz _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.056(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2257 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1135 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 1.02258(11) 0.0335(3) 0.15080(11) 0.0183(3) Uani 1 1 d . . . C2 C 1.02344(12) -0.1836(3) 0.11337(11) 0.0192(4) Uani 1 1 d . . . C3 C 0.93458(13) -0.2797(3) 0.06080(12) 0.0214(4) Uani 1 1 d . . . C4 C 0.84652(12) -0.1623(3) 0.04505(12) 0.0223(4) Uani 1 1 d . . . C5 C 0.84595(12) 0.0520(3) 0.08180(12) 0.0214(4) Uani 1 1 d . . . C6 C 0.93254(12) 0.1498(3) 0.13493(11) 0.0197(4) Uani 1 1 d . . . C7 C 1.11412(12) 0.1449(3) 0.20256(11) 0.0203(4) Uani 1 1 d . . . N8 N 1.19850(10) 0.0476(2) 0.21720(10) 0.0222(3) Uani 1 1 d . . . C9 C 1.28653(13) 0.1754(3) 0.26711(13) 0.0257(4) Uani 1 1 d . . . C10 C 1.35601(12) 0.2046(3) 0.19996(12) 0.0207(4) Uani 1 1 d . . . C11 C 1.35684(12) 0.4027(3) 0.14907(13) 0.0232(4) Uani 1 1 d . . . N12 N 1.41573(11) 0.4426(3) 0.08776(11) 0.0258(4) Uani 1 1 d . . . C13 C 1.47704(12) 0.2777(3) 0.07598(12) 0.0245(4) Uani 1 1 d . . . C14 C 1.48118(13) 0.0740(3) 0.12271(13) 0.0246(4) Uani 1 1 d . . . C15 C 1.41961(13) 0.0362(3) 0.18547(12) 0.0233(4) Uani 1 1 d . . . O16 O 1.10850(9) -0.3029(2) 0.12649(9) 0.0246(3) Uani 1 1 d . . . Cl17 Cl 0.73561(3) 0.20355(8) 0.05715(3) 0.0331(2) Uani 1 1 d . . . H3 H 0.9330(15) -0.426(4) 0.0354(16) 0.0279(16) Uiso 1 1 d . . . H4 H 0.7862(17) -0.227(4) 0.0098(16) 0.0279(16) Uiso 1 1 d . . . H6 H 0.9325(16) 0.300(4) 0.1617(16) 0.0279(16) Uiso 1 1 d . . . H7 H 1.1088(16) 0.301(4) 0.2249(16) 0.0279(16) Uiso 1 1 d . . . H9A H 1.2686(16) 0.329(4) 0.2883(16) 0.0279(16) Uiso 1 1 d . . . H9B H 1.3188(15) 0.089(4) 0.3275(16) 0.0279(16) Uiso 1 1 d . . . H11 H 1.3131(16) 0.517(4) 0.1569(16) 0.0279(16) Uiso 1 1 d . . . H13 H 1.5199(16) 0.308(4) 0.0314(16) 0.0279(16) Uiso 1 1 d . . . H14 H 1.5259(16) -0.038(4) 0.1115(16) 0.0279(16) Uiso 1 1 d . . . H15 H 1.4228(16) -0.099(4) 0.2195(16) 0.0279(16) Uiso 1 1 d . . . H16 H 1.1547(17) -0.211(4) 0.1554(16) 0.0279(16) Uiso 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 0.0207(8) 0.0201(8) 0.0150(7) 0.0018(6) 0.0061(6) -0.0015(6) C2 0.0223(8) 0.0199(8) 0.0174(7) 0.0029(6) 0.0089(6) 0.0014(6) C3 0.0267(9) 0.0204(9) 0.0187(8) -0.0026(6) 0.0087(6) -0.0023(6) C4 0.0212(8) 0.0290(9) 0.0166(7) -0.0008(6) 0.0044(6) -0.0053(7) C5 0.0198(8) 0.0261(9) 0.0186(8) 0.0025(6) 0.0051(6) 0.0030(6) C6 0.0237(8) 0.0185(9) 0.0179(7) 0.0013(6) 0.0068(6) 0.0011(6) C7 0.0242(8) 0.0213(9) 0.0169(7) 0.0013(6) 0.0081(6) -0.0025(6) N8 0.0199(7) 0.0271(8) 0.0203(7) 0.0015(6) 0.0060(5) -0.0037(6) C9 0.0201(8) 0.0360(11) 0.0212(8) -0.0023(7) 0.0051(6) -0.0062(7) C10 0.0153(7) 0.0269(9) 0.0185(7) -0.0027(6) 0.0014(6) -0.0038(6) C11 0.0183(8) 0.0247(9) 0.0263(8) -0.0001(7) 0.0050(6) 0.0018(7) N12 0.0224(7) 0.0278(9) 0.0277(8) 0.0045(6) 0.0071(6) 0.0009(6) C13 0.0195(8) 0.0329(10) 0.0217(8) 0.0007(7) 0.0062(6) -0.0008(7) C14 0.0226(8) 0.0277(10) 0.0231(8) -0.0028(7) 0.0049(6) 0.0043(7) C15 0.0254(8) 0.0217(9) 0.0208(8) 0.0009(6) 0.0019(6) -0.0025(6) O16 0.0222(6) 0.0220(7) 0.0308(7) -0.0018(5) 0.0086(5) 0.0033(5) Cl17 0.0207(3) 0.0378(3) 0.0379(3) -0.00160(19) 0.00167(18) 0.00802(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.400(2) . ? C1 C2 1.406(2) . ? C1 C7 1.463(2) . ? C2 O16 1.354(2) . ? C2 C3 1.399(2) . ? C3 C4 1.380(2) . ? C3 H3 0.95(2) . ? C4 C5 1.387(3) . ? C4 H4 0.95(2) . ? C5 C6 1.382(2) . ? C5 Cl17 1.7416(17) . ? C6 H6 0.98(2) . ? C7 N8 1.279(2) . ? C7 H7 1.00(2) . ? N8 C9 1.469(2) . ? C9 C10 1.512(2) . ? C9 H9A 1.02(2) . ? C9 H9B 1.00(2) . ? C10 C15 1.388(2) . ? C10 C11 1.389(3) . ? C11 N12 1.343(2) . ? C11 H11 0.94(2) . ? N12 C13 1.341(2) . ? C13 C14 1.382(3) . ? C13 H13 0.98(2) . ? C14 C15 1.385(2) . ? C14 H14 0.95(2) . ? C15 H15 0.94(2) . ? O16 H16 0.87(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 C6 C1 C2 119.35(15) . . ? C6 C1 C7 118.96(15) . . ? C2 C1 C7 121.64(15) . . ? O16 C2 C3 118.75(15) . . ? O16 C2 C1 121.67(15) . . ? C3 C2 C1 119.58(15) . . ? C4 C3 C2 120.43(16) . . ? C4 C3 H3 118.3(13) . . ? C2 C3 H3 121.3(13) . . ? C3 C4 C5 119.86(16) . . ? C3 C4 H4 120.8(13) . . ? C5 C4 H4 119.3(13) . . ? C6 C5 C4 120.86(15) . . ? C6 C5 Cl17 119.48(14) . . ? C4 C5 Cl17 119.63(13) . . ? C5 C6 C1 119.92(16) . . ? C5 C6 H6 121.2(12) . . ? C1 C6 H6 118.8(13) . . ? N8 C7 C1 121.43(16) . . ? N8 C7 H7 120.9(12) . . ? C1 C7 H7 117.7(12) . . ? C7 N8 C9 117.45(16) . . ? N8 C9 C10 110.13(14) . . ? N8 C9 H9A 112.3(12) . . ? C10 C9 H9A 108.3(12) . . ? N8 C9 H9B 106.4(12) . . ? C10 C9 H9B 111.5(12) . . ? H9A C9 H9B 108.3(17) . . ? C15 C10 C11 117.63(15) . . ? C15 C10 C9 122.00(16) . . ? C11 C10 C9 120.36(16) . . ? N12 C11 C10 124.34(16) . . ? N12 C11 H11 117.0(13) . . ? C10 C11 H11 118.7(13) . . ? C13 N12 C11 116.65(15) . . ? N12 C13 C14 123.36(15) . . ? N12 C13 H13 116.3(13) . . ? C14 C13 H13 120.3(13) . . ? C13 C14 C15 119.02(16) . . ? C13 C14 H14 120.0(13) . . ? C15 C14 H14 121.0(13) . . ? C14 C15 C10 119.00(17) . . ? C14 C15 H15 120.3(13) . . ? C10 C15 H15 120.7(13) . . ? C2 O16 H16 104.3(15) . . ? 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 O16 179.85(14) . . . . ? C7 C1 C2 O16 2.4(2) . . . . ? C6 C1 C2 C3 0.1(2) . . . . ? C7 C1 C2 C3 -177.31(15) . . . . ? O16 C2 C3 C4 -179.34(14) . . . . ? C1 C2 C3 C4 0.4(2) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C6 -0.5(2) . . . . ? C3 C4 C5 Cl17 177.22(13) . . . . ? C4 C5 C6 C1 1.1(2) . . . . ? Cl17 C5 C6 C1 -176.70(11) . . . . ? C2 C1 C6 C5 -0.9(2) . . . . ? C7 C1 C6 C5 176.65(14) . . . . ? C6 C1 C7 N8 -178.59(14) . . . . ? C2 C1 C7 N8 -1.1(2) . . . . ? C1 C7 N8 C9 178.12(14) . . . . ? C7 N8 C9 C10 -117.43(17) . . . . ? N8 C9 C10 C15 -79.3(2) . . . . ? N8 C9 C10 C11 99.74(19) . . . . ? C15 C10 C11 N12 -0.7(3) . . . . ? C9 C10 C11 N12 -179.76(16) . . . . ? C10 C11 N12 C13 0.1(3) . . . . ? C11 N12 C13 C14 0.4(3) . . . . ? N12 C13 C14 C15 -0.3(3) . . . . ? C13 C14 C15 C10 -0.4(2) . . . . ? C11 C10 C15 C14 0.8(2) . . . . ? C9 C10 C15 C14 179.84(15) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.251 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.075