# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Imai, Yoshitane' _publ_contact_author_email y-imai@apch.kindai.ac.jp _publ_section_title ; Chiral crystallization of ether- and imide-bridged biphenyl compounds without any outside chiral source ; loop_ _publ_author_name T.Kinuta T.Sato N.Tajima R.Kuroda Y.Matsubara Y.Imai # Attachment '- 31840a-2.cif' data_31840a-1 _database_code_depnum_ccdc_archive 'CCDC 768631' #TrackingRef '- 31840a-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H8 O3' _chemical_formula_weight 224.20 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 17.034(3) _cell_length_b 3.8930(6) _cell_length_c 7.3497(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 487.39(13) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1085 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 28.30 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9580 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3565 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 28.30 _reflns_number_total 1214 _reflns_number_gt 1085 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0550P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(15) _refine_ls_number_reflns 1214 _refine_ls_number_parameters 78 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0877 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 0.95912(8) 0.0661(4) 0.72727(18) 0.0149(3) Uani 1 1 d . . . C2 C 0.90831(8) 0.0421(4) 0.87685(17) 0.0168(3) Uani 1 1 d . . . C3 C 0.83030(8) 0.1493(4) 0.8631(2) 0.0187(3) Uani 1 1 d . . . H3 H 0.7961 0.1231 0.9642 0.022 Uiso 1 1 calc R . . C4 C 0.80256(8) 0.2928(4) 0.7041(2) 0.0199(3) Uani 1 1 d . . . H4 H 0.7499 0.3723 0.6966 0.024 Uiso 1 1 calc R . . C5 C 0.85235(9) 0.3202(4) 0.55488(19) 0.0197(3) Uani 1 1 d . . . H5 H 0.8337 0.4190 0.4449 0.024 Uiso 1 1 calc R . . C6 C 0.92862(8) 0.2045(4) 0.56606(19) 0.0174(3) Uani 1 1 d . . . H6 H 0.9614 0.2189 0.4618 0.021 Uiso 1 1 calc R . . C7 C 0.93018(8) -0.1023(4) 1.05659(19) 0.0190(3) Uani 1 1 d . . . O8 O 0.88792(7) -0.2736(3) 1.14900(14) 0.0276(3) Uani 1 1 d . . . O9 O 1.0000 0.0000 1.13491(17) 0.0250(4) Uani 1 2 d S . . 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 0.0191(7) 0.0133(6) 0.0123(6) -0.0015(5) -0.0008(5) -0.0021(6) C2 0.0230(7) 0.0145(7) 0.0129(6) -0.0011(5) -0.0012(5) -0.0013(6) C3 0.0215(7) 0.0175(7) 0.0171(7) -0.0018(6) 0.0034(5) -0.0026(5) C4 0.0171(7) 0.0185(7) 0.0241(7) -0.0016(6) -0.0024(6) -0.0007(6) C5 0.0248(7) 0.0184(7) 0.0161(6) 0.0012(6) -0.0052(6) -0.0022(6) C6 0.0235(7) 0.0166(6) 0.0122(6) -0.0005(6) -0.0004(6) -0.0033(6) C7 0.0236(7) 0.0193(7) 0.0141(6) -0.0011(6) 0.0041(6) 0.0042(6) O8 0.0391(6) 0.0271(6) 0.0166(5) 0.0036(5) 0.0066(4) -0.0010(5) O9 0.0240(8) 0.0408(10) 0.0101(6) 0.000 0.000 0.0031(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.4014(19) . ? C1 C2 1.4023(18) . ? C1 C1 1.485(3) 2_755 ? C2 C3 1.3965(19) . ? C2 C7 1.4832(18) . ? C3 C4 1.379(2) . ? C4 C5 1.391(2) . ? C5 C6 1.378(2) . ? C7 O8 1.1933(17) . ? C7 O9 1.3801(16) . ? O9 C7 1.3801(16) 2_755 ? 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 117.37(12) . . ? C6 C1 C1 118.75(9) . 2_755 ? C2 C1 C1 123.76(9) . 2_755 ? C3 C2 C1 120.71(12) . . ? C3 C2 C7 114.61(12) . . ? C1 C2 C7 124.65(12) . . ? C4 C3 C2 120.55(13) . . ? C3 C4 C5 119.38(13) . . ? C6 C5 C4 120.20(13) . . ? C5 C6 C1 121.71(14) . . ? O8 C7 O9 116.34(13) . . ? O8 C7 C2 124.56(13) . . ? O9 C7 C2 118.59(12) . . ? C7 O9 C7 130.70(15) . 2_755 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.283 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.047 #===END data_31840a-2 _database_code_depnum_ccdc_archive 'CCDC 768632' #TrackingRef '- 31840a-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H13 N O2' _chemical_formula_sum 'C20 H13 N O2' _chemical_formula_weight 299.31 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 Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.0648(4) _cell_length_b 15.6753(14) _cell_length_c 21.9435(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1398.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3478 _cell_measurement_theta_min 1.60 _cell_measurement_theta_max 28.28 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7881 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10420 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3478 _reflns_number_gt 2871 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0411P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(10) _refine_ls_number_reflns 3478 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 0.924 _refine_ls_restrained_S_all 0.924 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4414(4) 0.20004(9) 0.73847(6) 0.0169(3) Uani 1 1 d . . . C2 C 0.4405(4) 0.11089(9) 0.73888(6) 0.0166(3) Uani 1 1 d . . . C3 C 0.5591(4) 0.06622(9) 0.78970(6) 0.0192(3) Uani 1 1 d . . . H3 H 0.5513 0.0069 0.7901 0.023 Uiso 1 1 calc R . . C4 C 0.6877(4) 0.10956(10) 0.83929(6) 0.0217(3) Uani 1 1 d . . . H4 H 0.7732 0.0796 0.8723 0.026 Uiso 1 1 calc R . . C5 C 0.6879(4) 0.19767(10) 0.83931(6) 0.0221(3) Uani 1 1 d . . . H5 H 0.7712 0.2271 0.8727 0.027 Uiso 1 1 calc R . . C6 C 0.5652(4) 0.24229(9) 0.79008(6) 0.0203(3) Uani 1 1 d . . . H6 H 0.5644 0.3016 0.7911 0.024 Uiso 1 1 calc R . . C7 C 0.3179(3) 0.25167(9) 0.68705(6) 0.0166(3) Uani 1 1 d . . . C8 C 0.3742(3) 0.22886(8) 0.62595(6) 0.0162(3) Uani 1 1 d . . . C9 C 0.2850(4) 0.28450(9) 0.57922(6) 0.0193(3) Uani 1 1 d . . . H9 H 0.3332 0.2703 0.5390 0.023 Uiso 1 1 calc R . . C10 C 0.1264(4) 0.36027(9) 0.59168(7) 0.0222(3) Uani 1 1 d . . . H10 H 0.0647 0.3964 0.5601 0.027 Uiso 1 1 calc R . . C11 C 0.0595(4) 0.38217(9) 0.65143(7) 0.0220(3) Uani 1 1 d . . . H11 H -0.0523 0.4325 0.6601 0.026 Uiso 1 1 calc R . . C12 C 0.1586(4) 0.32926(9) 0.69842(6) 0.0198(3) Uani 1 1 d . . . H12 H 0.1186 0.3456 0.7385 0.024 Uiso 1 1 calc R . . C13 C 0.3184(4) 0.05324(9) 0.68937(6) 0.0164(3) Uani 1 1 d . . . O14 O 0.1729(3) -0.01196(6) 0.70184(4) 0.0217(2) Uani 1 1 d . . . C15 C 0.5258(3) 0.14778(9) 0.60433(5) 0.0157(3) Uani 1 1 d . . . O16 O 0.7037(2) 0.14686(6) 0.56011(4) 0.0204(2) Uani 1 1 d . . . N17 N 0.4162(3) 0.06889(7) 0.62897(5) 0.0154(3) Uani 1 1 d . . . C18 C 0.4273(4) -0.00372(8) 0.58775(6) 0.0157(3) Uani 1 1 d . . . C19 C 0.6036(4) -0.07583(9) 0.60382(6) 0.0194(3) Uani 1 1 d . . . H19 H 0.7122 -0.0785 0.6411 0.023 Uiso 1 1 calc R . . C20 C 0.6164(4) -0.14395(9) 0.56376(6) 0.0235(3) Uani 1 1 d . . . H20 H 0.7298 -0.1932 0.5747 0.028 Uiso 1 1 calc R . . C21 C 0.4629(4) -0.13952(10) 0.50785(7) 0.0254(4) Uani 1 1 d . . . H21 H 0.4759 -0.1851 0.4809 0.030 Uiso 1 1 calc R . . C22 C 0.2890(4) -0.06683(10) 0.49206(6) 0.0239(3) Uani 1 1 d . . . H22 H 0.1863 -0.0637 0.4543 0.029 Uiso 1 1 calc R . . C23 C 0.2670(4) 0.00133(9) 0.53214(6) 0.0193(3) Uani 1 1 d . . . H23 H 0.1464 0.0497 0.5219 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0149(7) 0.0202(7) 0.0156(7) -0.0017(6) 0.0040(6) -0.0001(6) C2 0.0150(7) 0.0218(8) 0.0129(7) -0.0014(6) 0.0029(6) 0.0002(6) C3 0.0202(7) 0.0210(7) 0.0165(7) 0.0003(6) 0.0037(6) 0.0020(7) C4 0.0217(8) 0.0312(8) 0.0121(7) 0.0016(6) -0.0003(7) 0.0043(7) C5 0.0218(8) 0.0303(8) 0.0143(7) -0.0078(6) -0.0007(6) -0.0009(7) C6 0.0217(8) 0.0199(8) 0.0192(7) -0.0041(6) 0.0034(6) -0.0006(6) C7 0.0157(7) 0.0160(7) 0.0180(7) -0.0019(6) 0.0000(6) -0.0029(6) C8 0.0151(7) 0.0141(7) 0.0195(7) -0.0012(6) -0.0015(6) -0.0020(6) C9 0.0211(8) 0.0198(7) 0.0169(7) 0.0007(6) -0.0017(6) -0.0043(6) C10 0.0233(8) 0.0178(7) 0.0256(7) 0.0050(6) -0.0048(6) -0.0003(6) C11 0.0196(8) 0.0149(7) 0.0314(8) -0.0016(6) -0.0013(7) 0.0009(6) C12 0.0194(8) 0.0192(7) 0.0208(7) -0.0041(6) 0.0020(6) -0.0012(6) C13 0.0179(7) 0.0160(7) 0.0152(7) 0.0026(5) 0.0008(6) 0.0028(6) O14 0.0279(6) 0.0197(5) 0.0175(5) -0.0002(4) 0.0025(5) -0.0054(5) C15 0.0164(7) 0.0169(7) 0.0138(6) 0.0004(6) -0.0035(5) -0.0002(6) O16 0.0242(6) 0.0204(5) 0.0168(5) 0.0008(4) 0.0035(4) -0.0012(5) N17 0.0204(6) 0.0131(6) 0.0127(5) -0.0005(4) -0.0001(5) -0.0002(5) C18 0.0185(7) 0.0143(7) 0.0142(6) -0.0008(5) 0.0032(6) -0.0046(6) C19 0.0214(8) 0.0186(7) 0.0181(7) 0.0015(6) 0.0020(6) -0.0028(6) C20 0.0253(8) 0.0157(7) 0.0296(8) 0.0005(6) 0.0074(7) -0.0006(7) C21 0.0287(9) 0.0222(8) 0.0253(8) -0.0112(6) 0.0101(7) -0.0085(7) C22 0.0229(8) 0.0329(9) 0.0158(7) -0.0045(6) 0.0016(6) -0.0090(7) C23 0.0199(8) 0.0224(7) 0.0156(7) 0.0002(6) 0.0020(6) -0.0026(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3975(18) . ? C1 C6 1.4050(19) . ? C1 C7 1.4766(19) . ? C2 C3 1.4023(19) . ? C2 C13 1.4977(19) . ? C3 C4 1.385(2) . ? C4 C5 1.3811(19) . ? C5 C6 1.3804(19) . ? C7 C12 1.4001(19) . ? C7 C8 1.4063(19) . ? C8 C9 1.3943(19) . ? C8 C15 1.4899(19) . ? C9 C10 1.379(2) . ? C10 C11 1.382(2) . ? C11 C12 1.3833(19) . ? C13 O14 1.2122(16) . ? C13 N17 1.4053(17) . ? C15 O16 1.2103(15) . ? C15 N17 1.4212(17) . ? N17 C18 1.4544(16) . ? C18 C19 1.3840(19) . ? C18 C23 1.3858(19) . ? C19 C20 1.3840(19) . ? C20 C21 1.378(2) . ? C21 C22 1.385(2) . ? C22 C23 1.3867(19) . ? 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 117.85(13) . . ? C2 C1 C7 123.51(12) . . ? C6 C1 C7 118.64(12) . . ? C1 C2 C3 120.24(13) . . ? C1 C2 C13 126.84(12) . . ? C3 C2 C13 112.92(12) . . ? C4 C3 C2 120.63(13) . . ? C5 C4 C3 119.41(13) . . ? C6 C5 C4 120.42(13) . . ? C5 C6 C1 121.42(13) . . ? C12 C7 C8 117.78(12) . . ? C12 C7 C1 119.81(12) . . ? C8 C7 C1 122.25(12) . . ? C9 C8 C7 119.99(13) . . ? C9 C8 C15 114.01(12) . . ? C7 C8 C15 126.01(12) . . ? C10 C9 C8 120.97(13) . . ? C9 C10 C11 119.60(13) . . ? C10 C11 C12 120.05(13) . . ? C11 C12 C7 121.52(13) . . ? O14 C13 N17 119.87(12) . . ? O14 C13 C2 120.45(12) . . ? N17 C13 C2 119.02(12) . . ? O16 C15 N17 118.80(12) . . ? O16 C15 C8 120.83(13) . . ? N17 C15 C8 119.45(11) . . ? C13 N17 C15 126.82(11) . . ? C13 N17 C18 117.30(11) . . ? C15 N17 C18 115.76(10) . . ? C19 C18 C23 120.96(12) . . ? C19 C18 N17 119.78(12) . . ? C23 C18 N17 119.23(12) . . ? C18 C19 C20 119.19(13) . . ? C21 C20 C19 120.63(14) . . ? C20 C21 C22 119.69(13) . . ? C21 C22 C23 120.55(14) . . ? C18 C23 C22 118.96(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 C6 C1 C2 C3 0.2(2) . . . . ? C7 C1 C2 C3 -179.36(13) . . . . ? C6 C1 C2 C13 179.46(13) . . . . ? C7 C1 C2 C13 -0.1(2) . . . . ? C1 C2 C3 C4 -2.0(2) . . . . ? C13 C2 C3 C4 178.70(13) . . . . ? C2 C3 C4 C5 2.3(2) . . . . ? C3 C4 C5 C6 -0.9(2) . . . . ? C4 C5 C6 C1 -0.9(2) . . . . ? C2 C1 C6 C5 1.2(2) . . . . ? C7 C1 C6 C5 -179.20(13) . . . . ? C2 C1 C7 C12 144.88(15) . . . . ? C6 C1 C7 C12 -34.7(2) . . . . ? C2 C1 C7 C8 -39.7(2) . . . . ? C6 C1 C7 C8 140.67(14) . . . . ? C12 C7 C8 C9 2.7(2) . . . . ? C1 C7 C8 C9 -172.77(13) . . . . ? C12 C7 C8 C15 -177.18(13) . . . . ? C1 C7 C8 C15 7.3(2) . . . . ? C7 C8 C9 C10 -3.3(2) . . . . ? C15 C8 C9 C10 176.63(13) . . . . ? C8 C9 C10 C11 1.1(2) . . . . ? C9 C10 C11 C12 1.6(2) . . . . ? C10 C11 C12 C7 -2.1(2) . . . . ? C8 C7 C12 C11 -0.1(2) . . . . ? C1 C7 C12 C11 175.53(14) . . . . ? C1 C2 C13 O14 -141.78(16) . . . . ? C3 C2 C13 O14 37.49(19) . . . . ? C1 C2 C13 N17 47.6(2) . . . . ? C3 C2 C13 N17 -133.17(14) . . . . ? C9 C8 C15 O16 35.90(19) . . . . ? C7 C8 C15 O16 -144.21(14) . . . . ? C9 C8 C15 N17 -133.01(13) . . . . ? C7 C8 C15 N17 46.88(19) . . . . ? O14 C13 N17 C15 166.11(14) . . . . ? C2 C13 N17 C15 -23.2(2) . . . . ? O14 C13 N17 C18 -18.0(2) . . . . ? C2 C13 N17 C18 152.69(13) . . . . ? O16 C15 N17 C13 154.74(13) . . . . ? C8 C15 N17 C13 -36.12(19) . . . . ? O16 C15 N17 C18 -21.19(18) . . . . ? C8 C15 N17 C18 147.95(13) . . . . ? C13 N17 C18 C19 -53.00(18) . . . . ? C15 N17 C18 C19 123.34(14) . . . . ? C13 N17 C18 C23 128.56(14) . . . . ? C15 N17 C18 C23 -55.11(18) . . . . ? C23 C18 C19 C20 -0.6(2) . . . . ? N17 C18 C19 C20 -178.99(13) . . . . ? C18 C19 C20 C21 1.6(2) . . . . ? C19 C20 C21 C22 -1.2(2) . . . . ? C20 C21 C22 C23 -0.3(2) . . . . ? C19 C18 C23 C22 -0.9(2) . . . . ? N17 C18 C23 C22 177.54(13) . . . . ? C21 C22 C23 C18 1.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.236 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.044 #===END data_31840a-3 _database_code_depnum_ccdc_archive 'CCDC 768633' #TrackingRef '- 31840a-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H12 N2 O2' _chemical_formula_weight 300.31 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 Orthorhombic _symmetry_space_group_name_H-M 'C 2 2 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 3.9147(7) _cell_length_b 22.823(4) _cell_length_c 15.634(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1396.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1727 _cell_measurement_theta_min 1.78 _cell_measurement_theta_max 28.29 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.095 _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 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4688 _diffrn_reflns_av_R_equivalents 0.1122 _diffrn_reflns_av_sigmaI/netI 0.1024 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.29 _reflns_number_total 1727 _reflns_number_gt 1472 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0258P)^2^+17.4718P] 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 SHELXL _refine_ls_extinction_coef 0.0000(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(6) _refine_ls_number_reflns 1727 _refine_ls_number_parameters 69 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1492 _refine_ls_R_factor_gt 0.1330 _refine_ls_wR_factor_ref 0.2483 _refine_ls_wR_factor_gt 0.2422 _refine_ls_goodness_of_fit_ref 1.278 _refine_ls_restrained_S_all 1.278 _refine_ls_shift/su_max 1.406 _refine_ls_shift/su_mean 0.032 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 0.5496(14) 0.1329(2) 0.2967(3) 0.0051(11) Uiso 1 1 d . . . C2 C 0.4984(16) 0.1811(2) 0.3497(3) 0.0064(11) Uani 1 1 d . . . C3 C 0.5646(16) 0.1768(3) 0.4383(4) 0.0093(12) Uiso 1 1 d . . . H3 H 0.5202 0.2083 0.4744 0.011 Uiso 1 1 calc R . . C4 C 0.6963(17) 0.1252(3) 0.4703(4) 0.0117(13) Uiso 1 1 d . . . H4 H 0.7455 0.1224 0.5284 0.014 Uiso 1 1 calc R . . C5 C 0.7563(17) 0.0777(3) 0.4180(4) 0.0128(13) Uani 1 1 d . . . H5 H 0.8489 0.0434 0.4404 0.015 Uiso 1 1 calc R . . C6 C 0.6778(16) 0.0815(3) 0.3324(4) 0.0103(12) Uiso 1 1 d . . . H6 H 0.7110 0.0489 0.2975 0.012 Uiso 1 1 calc R . . C7 C 0.3687(14) 0.2404(2) 0.3253(3) 0.0045(11) Uiso 1 1 d . . . O8 O 0.1916(11) 0.26900(16) 0.3718(2) 0.0081(9) Uiso 1 1 d . . . N9 N 0.5000 0.2671(3) 0.2500 0.0056(13) Uani 1 2 d S . . C10 C 0.5000 0.3318(4) 0.2500 0.0122(18) Uiso 1 2 d S . . C11 C 0.3528(16) 0.3616(2) 0.1826(3) 0.0088(12) Uani 1 1 d . . . H11 H 0.2522 0.3420 0.1369 0.011 Uiso 1 1 calc R . . C12 C 0.3627(16) 0.4227(3) 0.1864(4) 0.0133(13) Uiso 1 1 d . . . H12 H 0.2660 0.4432 0.1411 0.016 Uiso 1 1 calc R . . N13 N 0.5000 0.4540(3) 0.2500 0.0149(17) Uani 1 2 d S . . 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 C2 0.004(2) 0.008(2) 0.007(2) 0.006(2) -0.002(2) -0.001(2) C5 0.014(3) 0.010(3) 0.014(3) 0.009(2) 0.000(2) 0.005(2) N9 0.010(3) 0.000(3) 0.007(3) 0.000 -0.003(3) 0.000 C11 0.014(3) 0.011(3) 0.001(2) -0.002(2) 0.002(2) -0.003(2) N13 0.026(4) 0.000(3) 0.019(4) 0.000 0.012(4) 0.000 _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 1.391(8) . ? C1 C6 1.394(8) . ? C1 C1 1.510(10) 3_655 ? C2 C3 1.411(8) . ? C2 C7 1.496(7) . ? C3 C4 1.380(8) . ? C4 C5 1.378(8) . ? C5 C6 1.377(8) . ? C7 O8 1.199(6) . ? C7 N9 1.421(6) . ? N9 C7 1.421(6) 3_655 ? N9 C10 1.477(10) . ? C10 C11 1.381(7) 3_655 ? C10 C11 1.381(7) . ? C11 C12 1.394(8) . ? C12 N13 1.337(7) . ? N13 C12 1.337(7) 3_655 ? 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 118.6(5) . . ? C2 C1 C1 122.6(4) . 3_655 ? C6 C1 C1 118.6(3) . 3_655 ? C1 C2 C3 120.3(5) . . ? C1 C2 C7 127.7(5) . . ? C3 C2 C7 112.0(5) . . ? C4 C3 C2 118.9(5) . . ? C5 C4 C3 121.3(6) . . ? C6 C5 C4 119.3(6) . . ? C5 C6 C1 121.5(6) . . ? O8 C7 N9 118.6(5) . . ? O8 C7 C2 122.3(5) . . ? N9 C7 C2 118.5(5) . . ? C7 N9 C7 129.2(6) 3_655 . ? C7 N9 C10 115.4(3) 3_655 . ? C7 N9 C10 115.4(3) . . ? C11 C10 C11 120.9(8) 3_655 . ? C11 C10 N9 119.5(4) 3_655 . ? C11 C10 N9 119.5(4) . . ? C10 C11 C12 116.6(6) . . ? N13 C12 C11 125.3(6) . . ? C12 N13 C12 115.3(7) . 3_655 ? 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 -2.1(8) . . . . ? C1 C1 C2 C3 173.7(6) 3_655 . . . ? C6 C1 C2 C7 179.1(6) . . . . ? C1 C1 C2 C7 -5.0(10) 3_655 . . . ? C1 C2 C3 C4 3.1(9) . . . . ? C7 C2 C3 C4 -177.9(5) . . . . ? C2 C3 C4 C5 -1.5(10) . . . . ? C3 C4 C5 C6 -1.1(10) . . . . ? C4 C5 C6 C1 2.2(10) . . . . ? C2 C1 C6 C5 -0.6(8) . . . . ? C1 C1 C6 C5 -176.6(7) 3_655 . . . ? C1 C2 C7 O8 145.2(6) . . . . ? C3 C2 C7 O8 -33.7(8) . . . . ? C1 C2 C7 N9 -44.1(8) . . . . ? C3 C2 C7 N9 137.0(5) . . . . ? O8 C7 N9 C7 -160.9(6) . . . 3_655 ? C2 C7 N9 C7 28.0(4) . . . 3_655 ? O8 C7 N9 C10 19.1(6) . . . . ? C2 C7 N9 C10 -152.0(4) . . . . ? C7 N9 C10 C11 -127.8(4) 3_655 . . 3_655 ? C7 N9 C10 C11 52.2(4) . . . 3_655 ? C7 N9 C10 C11 52.2(4) 3_655 . . . ? C7 N9 C10 C11 -127.8(4) . . . . ? C11 C10 C11 C12 0.2(4) 3_655 . . . ? N9 C10 C11 C12 -179.8(4) . . . . ? C10 C11 C12 N13 -0.5(9) . . . . ? C11 C12 N13 C12 0.3(5) . . . 3_655 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.555 _refine_diff_density_min -0.586 _refine_diff_density_rms 0.134 #===END