# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author 'Dr. N. Casati' _publ_contact_author_email nicola.casati@diamond.ac.uk loop_ _publ_author_name 'Elena Marelli' 'Nicola Casati' 'Fabia Gozzo' 'Piero Macchi' 'Petra Simoncic' 'Angelo Sironi' data_4abp30 _database_code_depnum_ccdc_archive 'CCDC 800408' #TrackingRef '4abp_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-amino-benzophenone _chemical_formula_moiety 'C13 H11 N O' _chemical_formula_sum 'C13 H11 N O' _chemical_formula_weight 197.23 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 ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.3080(5) _cell_length_b 5.4673(4) _cell_length_c 12.0570(13) _cell_angle_alpha 90.00 _cell_angle_beta 97.814(11) _cell_angle_gamma 90.00 _cell_volume 542.57(8) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_preparation 'mounted in a diamond-anvil cell ' _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ; DAC absorption corrected with Absorb 6.0 (gaussian) (R.J. Angel, J. Appl. Cryst. 2004, 37(3), 486) Crystal absorption corrected with SADABS (empirical) Area-Detector Absorption Correction, (Siemens Industrial Automation, Inc.: Madison, WI, 1996) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_pressure 100 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1725 _diffrn_reflns_av_R_equivalents 0.0783 _diffrn_reflns_av_sigmaI/netI 0.1098 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 25.39 _reflns_number_total 615 _reflns_number_gt 294 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1234P)^2^+0.4182P] 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 615 _refine_ls_number_parameters 37 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1776 _refine_ls_R_factor_gt 0.1021 _refine_ls_wR_factor_ref 0.2870 _refine_ls_wR_factor_gt 0.2432 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.069 _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 0.3117(15) 0.195(2) 0.266(3) 0.069(4) Uiso 1 1 d . . . N1 N 0.9450(13) 0.519(2) 0.420(2) 0.085(4) Uiso 1 1 d . . . H1A H 0.9634 0.6537 0.4564 0.102 Uiso 1 1 calc R . . H1B H 1.0248 0.4350 0.4015 0.102 Uiso 1 1 calc R . . O1 O 0.1987(12) 0.2652(18) 0.325(2) 0.100(4) Uiso 1 1 d . . . C11 C 0.2710(10) 0.0283(13) 0.1784(15) 0.052(3) Uiso 1 1 d G . . C12 C 0.1673(10) -0.1675(16) 0.1888(15) 0.076(4) Uiso 1 1 d G . . H12 H 0.1268 -0.1939 0.2560 0.091 Uiso 1 1 calc R . . C13 C 0.1243(10) -0.3239(14) 0.0988(16) 0.076(5) Uiso 1 1 d G . . H13 H 0.0550 -0.4549 0.1057 0.091 Uiso 1 1 calc R . . C14 C 0.1849(13) -0.2844(19) -0.0017(15) 0.110(7) Uiso 1 1 d G . . H14 H 0.1562 -0.3891 -0.0619 0.132 Uiso 1 1 calc R . . C15 C 0.2886(13) -0.089(2) -0.0120(14) 0.106(6) Uiso 1 1 d G . . H15 H 0.3291 -0.0623 -0.0792 0.127 Uiso 1 1 calc R . . C16 C 0.3316(10) 0.0677(15) 0.0780(15) 0.082(5) Uiso 1 1 d G . . H16 H 0.4009 0.1987 0.0711 0.098 Uiso 1 1 calc R . . C21 C 0.4771(7) 0.2894(13) 0.3087(17) 0.061(4) Uiso 1 1 d G . . C22 C 0.6101(9) 0.1597(13) 0.2814(15) 0.056(4) Uiso 1 1 d G . . H22 H 0.5943 0.0221 0.2358 0.067 Uiso 1 1 calc R . . C23 C 0.7667(7) 0.2354(17) 0.3223(17) 0.062(4) Uiso 1 1 d G . . H23 H 0.8557 0.1486 0.3040 0.075 Uiso 1 1 calc R . . C24 C 0.7902(7) 0.441(2) 0.3904(18) 0.060(4) Uiso 1 1 d G . . C25 C 0.6572(10) 0.5707(18) 0.4177(16) 0.063(4) Uiso 1 1 d G . . H25 H 0.6730 0.7082 0.4633 0.075 Uiso 1 1 calc R . . C26 C 0.5006(8) 0.4949(13) 0.3769(17) 0.057(4) Uiso 1 1 d G . . H26 H 0.4116 0.5818 0.3951 0.069 Uiso 1 1 calc R . . _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.30(2) . ? C1 C11 1.40(3) . ? C1 C21 1.492(17) . ? N1 C24 1.356(13) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? 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 O1 C1 C11 118.7(13) . . ? O1 C1 C21 114(2) . . ? C11 C1 C21 126.8(15) . . ? C12 C11 C16 120.0 . . ? C12 C11 C1 121.3(12) . . ? C16 C11 C1 118.6(12) . . ? C11 C12 C13 120.0 . . ? C14 C13 C12 120.0 . . ? C15 C14 C13 120.0 . . ? C14 C15 C16 120.0 . . ? C15 C16 C11 120.0 . . ? C22 C21 C26 120.0 . . ? C22 C21 C1 117.8(9) . . ? C26 C21 C1 122.1(9) . . ? C23 C22 C21 120.0 . . ? C22 C23 C24 120.0 . . ? N1 C24 C25 122.2(9) . . ? N1 C24 C23 117.5(10) . . ? C25 C24 C23 120.0 . . ? C26 C25 C24 120.0 . . ? C25 C26 C21 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C21 C22 -57.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.308 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.308 _refine_diff_density_max 0.199 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.039 data_4abp11 _database_code_depnum_ccdc_archive 'CCDC 800409' #TrackingRef '4abp_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-amino-benzophenone _chemical_formula_moiety 'C13 H11 N O' _chemical_formula_sum 'C13 H11 N O' _chemical_formula_weight 197.23 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 ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.1397(14) _cell_length_b 5.2541(9) _cell_length_c 11.853(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.20(3) _cell_angle_gamma 90.00 _cell_volume 501.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_preparation 'mounted in a diamond-anvil cell ' _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ; DAC absorption corrected with Absorb 6.0 (gaussian) (R.J. Angel, J. Appl. Cryst. 2004, 37(3), 486) Crystal absorption corrected with SADABS (empirical) Area-Detector Absorption Correction, (Siemens Industrial Automation, Inc.: Madison, WI, 1996) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_pressure 600000 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1185 _diffrn_reflns_av_R_equivalents 0.1185 _diffrn_reflns_av_sigmaI/netI 0.1597 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 4.63 _diffrn_reflns_theta_max 23.23 _reflns_number_total 453 _reflns_number_gt 228 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1548P)^2^+1.1496P] 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 453 _refine_ls_number_parameters 37 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2030 _refine_ls_R_factor_gt 0.1185 _refine_ls_wR_factor_ref 0.3446 _refine_ls_wR_factor_gt 0.2773 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.090 _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 0.304(3) 0.199(4) 0.260(5) 0.051(6) Uiso 1 1 d . . . N1 N 0.9542(18) 0.562(4) 0.429(4) 0.062(7) Uiso 1 1 d . . . H1A H 1.0384 0.4805 0.4110 0.074 Uiso 1 1 calc R . . H1B H 0.9689 0.6956 0.4711 0.074 Uiso 1 1 calc R . . O1 O 0.1888(16) 0.255(2) 0.328(3) 0.056(5) Uiso 1 1 d . . . C11 C 0.2671(16) 0.024(2) 0.174(2) 0.042(6) Uiso 1 1 d G . . C12 C 0.1647(15) -0.186(3) 0.181(2) 0.032(5) Uiso 1 1 d G . . H12 H 0.1202 -0.2175 0.2476 0.038 Uiso 1 1 calc R . . C13 C 0.1289(14) -0.348(3) 0.088(2) 0.046(6) Uiso 1 1 d G . . H13 H 0.0604 -0.4886 0.0927 0.055 Uiso 1 1 calc R . . C14 C 0.196(2) -0.301(4) -0.012(2) 0.086(10) Uiso 1 1 d G . . H14 H 0.1715 -0.4100 -0.0736 0.103 Uiso 1 1 calc R . . C15 C 0.2979(19) -0.092(4) -0.018(2) 0.070(8) Uiso 1 1 d G . . H15 H 0.3425 -0.0604 -0.0850 0.085 Uiso 1 1 calc R . . C16 C 0.3337(14) 0.071(3) 0.074(2) 0.065(7) Uiso 1 1 d G . . H16 H 0.4022 0.2108 0.0699 0.078 Uiso 1 1 calc R . . C21 C 0.4753(10) 0.293(3) 0.314(3) 0.067(8) Uiso 1 1 d G . . C22 C 0.6133(14) 0.167(2) 0.284(3) 0.033(6) Uiso 1 1 d G . . H22 H 0.5996 0.0221 0.2388 0.040 Uiso 1 1 calc R . . C23 C 0.7718(11) 0.258(3) 0.322(3) 0.035(5) Uiso 1 1 d G . . H23 H 0.8641 0.1744 0.3025 0.042 Uiso 1 1 calc R . . C24 C 0.7922(11) 0.475(3) 0.390(3) 0.030(6) Uiso 1 1 d G . . C25 C 0.6542(15) 0.601(3) 0.419(2) 0.053(7) Uiso 1 1 d G . . H25 H 0.6679 0.7461 0.4648 0.064 Uiso 1 1 calc R . . C26 C 0.4957(12) 0.510(3) 0.381(3) 0.039(5) Uiso 1 1 d G . . H26 H 0.4034 0.5938 0.4010 0.047 Uiso 1 1 calc R . . _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 O1 1.36(4) . ? C1 C11 1.37(5) . ? C1 C21 1.53(3) . ? N1 C24 1.41(2) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? 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 O1 C1 C11 119.3(17) . . ? O1 C1 C21 110(3) . . ? C11 C1 C21 128(2) . . ? C1 C11 C12 123.9(18) . . ? C1 C11 C16 116.0(18) . . ? C12 C11 C16 120.0 . . ? C11 C12 C13 120.0 . . ? C14 C13 C12 120.0 . . ? C13 C14 C15 120.0 . . ? C16 C15 C14 120.0 . . ? C15 C16 C11 120.0 . . ? C22 C21 C26 120.0 . . ? C22 C21 C1 117.6(15) . . ? C26 C21 C1 122.1(14) . . ? C21 C22 C23 120.0 . . ? C24 C23 C22 120.0 . . ? C23 C24 C25 120.0 . . ? C23 C24 N1 118.9(13) . . ? C25 C24 N1 121.1(13) . . ? C26 C25 C24 120.0 . . ? C25 C26 C21 120.0 . . ? _diffrn_measured_fraction_theta_max 0.316 _diffrn_reflns_theta_full 23.23 _diffrn_measured_fraction_theta_full 0.316 _refine_diff_density_max 0.193 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.055 data_4abp31 _database_code_depnum_ccdc_archive 'CCDC 800410' #TrackingRef '4abp_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-amino-benzophenone _chemical_formula_moiety 'C13 H11 N O' _chemical_formula_sum 'C13 H11 N O' _chemical_formula_weight 197.23 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 ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.9530(18) _cell_length_b 3.8650(8) _cell_length_c 13.081(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.47(3) _cell_angle_gamma 90.00 _cell_volume 452.63(16) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_preparation 'mounted in a diamond-anvil cell ' _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ; DAC absorption corrected with Absorb 6.0 (gaussian) (R.J. Angel, J. Appl. Cryst. 2004, 37(3), 486) Crystal absorption corrected with SADABS (empirical) Area-Detector Absorption Correction, (Siemens Industrial Automation, Inc.: Madison, WI, 1996) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_pressure 1000000 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1443 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0824 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.55 _diffrn_reflns_theta_max 25.07 _reflns_number_total 632 _reflns_number_gt 401 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0526P)^2^+0.6697P] 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 632 _refine_ls_number_parameters 37 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1197 _refine_ls_R_factor_gt 0.0745 _refine_ls_wR_factor_ref 0.1658 _refine_ls_wR_factor_gt 0.1431 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.047 _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 0.3713(9) 0.2017(19) 0.2849(13) 0.039(3) Uiso 1 1 d . . . N1 N 0.9755(7) 0.3835(16) 0.3980(12) 0.056(3) Uiso 1 1 d . . . H1A H 1.0474 0.2916 0.3643 0.085 Uiso 1 1 calc R . . H1B H 0.9942 0.4987 0.4528 0.085 Uiso 1 1 calc R . . O1 O 0.2790(7) 0.2878(17) 0.3520(9) 0.0573(19) Uiso 1 1 d . . . C11 C 0.3117(6) 0.0459(12) 0.1885(7) 0.032(2) Uiso 1 1 d G . . C12 C 0.1812(6) -0.1454(13) 0.1988(7) 0.040(3) Uiso 1 1 d G . . H12 H 0.1420 -0.1853 0.2633 0.048 Uiso 1 1 calc R . . C13 C 0.1094(5) -0.2772(14) 0.1126(7) 0.039(3) Uiso 1 1 d G . . H13 H 0.0221 -0.4052 0.1195 0.047 Uiso 1 1 calc R . . C14 C 0.1680(6) -0.2177(17) 0.0161(7) 0.047(3) Uiso 1 1 d G . . H14 H 0.1200 -0.3059 -0.0415 0.057 Uiso 1 1 calc R . . C15 C 0.2985(6) -0.0264(16) 0.0058(7) 0.050(3) Uiso 1 1 d G . . H15 H 0.3377 0.0134 -0.0587 0.060 Uiso 1 1 calc R . . C16 C 0.3703(5) 0.1054(13) 0.0920(7) 0.032(2) Uiso 1 1 d G . . H16 H 0.4576 0.2334 0.0851 0.038 Uiso 1 1 calc R . . C21 C 0.5332(4) 0.2559(11) 0.3042(7) 0.035(2) Uiso 1 1 d G . . C22 C 0.6472(6) 0.1164(12) 0.2457(6) 0.036(2) Uiso 1 1 d G . . H22 H 0.6244 -0.0071 0.1865 0.043 Uiso 1 1 calc R . . C23 C 0.7953(5) 0.1614(16) 0.2755(7) 0.042(3) Uiso 1 1 d G . . H23 H 0.8716 0.0680 0.2363 0.050 Uiso 1 1 calc R . . C24 C 0.8294(4) 0.3459(19) 0.3638(7) 0.036(3) Uiso 1 1 d G . . C25 C 0.7154(6) 0.4854(17) 0.4224(6) 0.043(3) Uiso 1 1 d G . . H25 H 0.7382 0.6089 0.4815 0.051 Uiso 1 1 calc R . . C26 C 0.5673(5) 0.4404(12) 0.3926(6) 0.043(3) Uiso 1 1 d G . . H26 H 0.4910 0.5338 0.4318 0.052 Uiso 1 1 calc R . . _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 O1 1.255(13) . ? C1 C21 1.484(9) . ? C1 C11 1.492(14) . ? N1 C24 1.386(8) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? 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 O1 C1 C21 119.4(11) . . ? O1 C1 C11 117.7(7) . . ? C21 C1 C11 122.9(10) . . ? C12 C11 C16 120.0 . . ? C12 C11 C1 115.3(6) . . ? C16 C11 C1 124.4(6) . . ? C11 C12 C13 120.0 . . ? C14 C13 C12 120.0 . . ? C15 C14 C13 120.0 . . ? C14 C15 C16 120.0 . . ? C15 C16 C11 120.0 . . ? C22 C21 C26 120.0 . . ? C22 C21 C1 124.9(7) . . ? C26 C21 C1 115.0(7) . . ? C23 C22 C21 120.0 . . ? C22 C23 C24 120.0 . . ? N1 C24 C23 121.5(6) . . ? N1 C24 C25 118.5(6) . . ? C23 C24 C25 120.0 . . ? C26 C25 C24 120.0 . . ? C25 C26 C21 120.0 . . ? _diffrn_measured_fraction_theta_max 0.380 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.380 _refine_diff_density_max 0.202 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.044 data_4abp32 _database_code_depnum_ccdc_archive 'CCDC 800411' #TrackingRef '4abp_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-amino-benzophenone _chemical_formula_moiety 'C13 H11 N O' _chemical_formula_sum 'C13 H11 N O' _chemical_formula_weight 197.23 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 ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0470(5) _cell_length_b 3.6626(2) _cell_length_c 12.7481(15) _cell_angle_alpha 90.00 _cell_angle_beta 92.304(10) _cell_angle_gamma 90.00 _cell_volume 422.07(6) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_preparation 'mounted in a diamond-anvil cell ' _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ; DAC absorption corrected with Absorb 6.0 (gaussian) (R.J. Angel, J. Appl. Cryst. 2004, 37(3), 486) Crystal absorption corrected with SADABS (empirical) Area-Detector Absorption Correction, (Siemens Industrial Automation, Inc.: Madison, WI, 1996) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_pressure 2000000 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1313 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0878 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.51 _diffrn_reflns_theta_max 25.36 _reflns_number_total 575 _reflns_number_gt 362 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0764P)^2^+0.0173P] 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 575 _refine_ls_number_parameters 37 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1058 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1595 _refine_ls_wR_factor_gt 0.1389 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.047 _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 0.3953(8) 0.2009(19) 0.2888(12) 0.041(3) Uiso 1 1 d . . . N1 N 1.0006(6) 0.3826(16) 0.3923(10) 0.046(2) Uiso 1 1 d . . . H1A H 1.0684 0.2969 0.3538 0.068 Uiso 1 1 calc R . . H1B H 1.0246 0.4977 0.4493 0.068 Uiso 1 1 calc R . . O1 O 0.3101(5) 0.2991(16) 0.3592(8) 0.0487(18) Uiso 1 1 d . . . C11 C 0.3232(5) 0.0484(11) 0.1922(6) 0.031(2) Uiso 1 1 d G . . C12 C 0.1917(5) -0.1398(12) 0.2048(6) 0.031(2) Uiso 1 1 d G . . H12 H 0.1570 -0.1763 0.2717 0.038 Uiso 1 1 calc R . . C13 C 0.1120(4) -0.2733(14) 0.1176(7) 0.028(2) Uiso 1 1 d G . . H13 H 0.0240 -0.3992 0.1261 0.034 Uiso 1 1 calc R . . C14 C 0.1639(5) -0.2187(15) 0.0176(6) 0.038(2) Uiso 1 1 d G . . H14 H 0.1106 -0.3081 -0.0408 0.045 Uiso 1 1 calc R . . C15 C 0.2954(6) -0.0305(14) 0.0049(6) 0.043(3) Uiso 1 1 d G . . H15 H 0.3300 0.0060 -0.0620 0.051 Uiso 1 1 calc R . . C16 C 0.3750(4) 0.1030(12) 0.0922(7) 0.034(2) Uiso 1 1 d G . . H16 H 0.4630 0.2289 0.0837 0.040 Uiso 1 1 calc R . . C21 C 0.5547(3) 0.2499(11) 0.3091(6) 0.028(2) Uiso 1 1 d G . . C22 C 0.6608(5) 0.1084(12) 0.2445(6) 0.037(2) Uiso 1 1 d G . . H22 H 0.6317 -0.0149 0.1833 0.045 Uiso 1 1 calc R . . C23 C 0.8102(4) 0.1511(15) 0.2713(6) 0.033(2) Uiso 1 1 d G . . H23 H 0.8812 0.0564 0.2280 0.039 Uiso 1 1 calc R . . C24 C 0.8536(4) 0.3354(17) 0.3627(6) 0.035(2) Uiso 1 1 d G . . C25 C 0.7476(5) 0.4769(16) 0.4274(5) 0.038(2) Uiso 1 1 d G . . H25 H 0.7766 0.6002 0.4886 0.046 Uiso 1 1 calc R . . C26 C 0.5981(5) 0.4342(12) 0.4006(6) 0.038(2) Uiso 1 1 d G . . H26 H 0.5272 0.5289 0.4438 0.045 Uiso 1 1 calc R . . _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 O1 1.259(12) . ? C1 C21 1.466(8) . ? C1 C11 1.480(14) . ? N1 C24 1.379(7) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? 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 O1 C1 C21 117.7(10) . . ? O1 C1 C11 116.1(7) . . ? C21 C1 C11 126.2(9) . . ? C12 C11 C16 120.0 . . ? C12 C11 C1 116.2(5) . . ? C16 C11 C1 123.7(5) . . ? C13 C12 C11 120.0 . . ? C12 C13 C14 120.0 . . ? C15 C14 C13 120.0 . . ? C14 C15 C16 120.0 . . ? C15 C16 C11 120.0 . . ? C22 C21 C26 120.0 . . ? C22 C21 C1 123.2(6) . . ? C26 C21 C1 116.8(6) . . ? C23 C22 C21 120.0 . . ? C24 C23 C22 120.0 . . ? N1 C24 C23 121.8(6) . . ? N1 C24 C25 118.2(6) . . ? C23 C24 C25 120.0 . . ? C26 C25 C24 120.0 . . ? C25 C26 C21 120.0 . . ? _diffrn_measured_fraction_theta_max 0.361 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.361 _refine_diff_density_max 0.168 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.047 data_4abp33 _database_code_depnum_ccdc_archive 'CCDC 800413' #TrackingRef '4abp_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-amino-benzophenone _chemical_formula_moiety 'C13 H11 N O' _chemical_formula_sum 'C13 H11 N O' _chemical_formula_weight 197.23 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 ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0625(6) _cell_length_b 3.5605(2) _cell_length_c 12.5539(17) _cell_angle_alpha 90.00 _cell_angle_beta 92.541(11) _cell_angle_gamma 90.00 _cell_volume 404.68(7) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_preparation 'mounted in a diamond-anvil cell ' _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ; DAC absorption corrected with Absorb 6.0 (gaussian) (R.J. Angel, J. Appl. Cryst. 2004, 37(3), 486) Crystal absorption corrected with SADABS (empirical) Area-Detector Absorption Correction, (Siemens Industrial Automation, Inc.: Madison, WI, 1996) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_pressure 3500000 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1176 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0923 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.50 _diffrn_reflns_theta_max 23.25 _reflns_number_total 495 _reflns_number_gt 317 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0751P)^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_number_reflns 495 _refine_ls_number_parameters 37 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1081 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1613 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.079 _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 0.3976(10) 0.208(2) 0.2916(14) 0.039(3) Uiso 1 1 d . . . N1 N 1.0056(7) 0.3808(18) 0.3866(11) 0.041(2) Uiso 1 1 d . . . H1A H 1.0707 0.3011 0.3442 0.061 Uiso 1 1 calc R . . H1B H 1.0329 0.4945 0.4446 0.061 Uiso 1 1 calc R . . O1 O 0.3157(6) 0.3127(19) 0.3652(10) 0.050(2) Uiso 1 1 d . . . C11 C 0.3258(6) 0.0483(12) 0.1909(8) 0.028(3) Uiso 1 1 d G . . C12 C 0.1936(6) -0.1394(14) 0.2048(8) 0.029(3) Uiso 1 1 d G . . H12 H 0.1596 -0.1731 0.2730 0.035 Uiso 1 1 calc R . . C13 C 0.1120(5) -0.2766(16) 0.1168(8) 0.026(2) Uiso 1 1 d G . . H13 H 0.0235 -0.4021 0.1262 0.031 Uiso 1 1 calc R . . C14 C 0.1627(6) -0.2262(17) 0.0149(8) 0.036(3) Uiso 1 1 d G . . H14 H 0.1081 -0.3180 -0.0439 0.043 Uiso 1 1 calc R . . C15 C 0.2950(7) -0.0385(17) 0.0010(8) 0.044(3) Uiso 1 1 d G . . H15 H 0.3289 -0.0048 -0.0672 0.053 Uiso 1 1 calc R . . C16 C 0.3765(5) 0.0987(14) 0.0890(9) 0.034(3) Uiso 1 1 d G . . H16 H 0.4650 0.2243 0.0796 0.040 Uiso 1 1 calc R . . C21 C 0.5595(4) 0.2444(13) 0.3086(8) 0.029(3) Uiso 1 1 d G . . C22 C 0.6640(7) 0.1023(14) 0.2416(7) 0.038(3) Uiso 1 1 d G . . H22 H 0.6338 -0.0203 0.1789 0.046 Uiso 1 1 calc R . . C23 C 0.8137(6) 0.1436(18) 0.2681(7) 0.035(3) Uiso 1 1 d G . . H23 H 0.8836 0.0486 0.2232 0.042 Uiso 1 1 calc R . . C24 C 0.8589(4) 0.327(2) 0.3617(7) 0.032(3) Uiso 1 1 d G . . C25 C 0.7544(7) 0.4691(18) 0.4288(6) 0.032(3) Uiso 1 1 d G . . H25 H 0.7846 0.5918 0.4914 0.039 Uiso 1 1 calc R . . C26 C 0.6047(6) 0.4278(15) 0.4022(7) 0.037(3) Uiso 1 1 d G . . H26 H 0.5348 0.5229 0.4471 0.044 Uiso 1 1 calc R . . _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 O1 1.267(15) . ? C1 C21 1.479(10) . ? C1 C11 1.508(16) . ? N1 C24 1.366(8) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? 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 O1 C1 C21 118.6(13) . . ? O1 C1 C11 118.5(8) . . ? C21 C1 C11 122.9(10) . . ? C12 C11 C16 120.0 . . ? C12 C11 C1 114.7(6) . . ? C16 C11 C1 125.1(6) . . ? C13 C12 C11 120.0 . . ? C14 C13 C12 120.0 . . ? C13 C14 C15 120.0 . . ? C16 C15 C14 120.0 . . ? C15 C16 C11 120.0 . . ? C22 C21 C26 120.0 . . ? C22 C21 C1 125.4(7) . . ? C26 C21 C1 114.6(8) . . ? C21 C22 C23 120.0 . . ? C24 C23 C22 120.0 . . ? N1 C24 C23 120.4(7) . . ? N1 C24 C25 119.5(7) . . ? C23 C24 C25 120.0 . . ? C24 C25 C26 120.0 . . ? C25 C26 C21 120.0 . . ? _diffrn_measured_fraction_theta_max 0.412 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.412 _refine_diff_density_max 0.170 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.052 data_4abp34 _database_code_depnum_ccdc_archive 'CCDC 800414' #TrackingRef '4abp_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-amino-benzophenone _chemical_formula_moiety 'C13 H11 N O' _chemical_formula_sum 'C13 H11 N O' _chemical_formula_weight 197.23 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 ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0721(17) _cell_length_b 3.4383(6) _cell_length_c 12.285(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.72(3) _cell_angle_gamma 90.00 _cell_volume 382.77(18) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_preparation 'mounted in a diamond-anvil cell ' _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ; DAC absorption corrected with Absorb 6.0 (gaussian) (R.J. Angel, J. Appl. Cryst. 2004, 37(3), 486) Crystal absorption corrected with SADABS (empirical) Area-Detector Absorption Correction, (Siemens Industrial Automation, Inc.: Madison, WI, 1996) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_pressure 6200000 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1126 _diffrn_reflns_av_R_equivalents 0.0490 _diffrn_reflns_av_sigmaI/netI 0.0630 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 4.50 _diffrn_reflns_theta_max 23.24 _reflns_number_total 447 _reflns_number_gt 332 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0623P)^2^+0.0655P] 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 447 _refine_ls_number_parameters 37 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.076 _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 0.4024(7) 0.2075(17) 0.2951(12) 0.031(2) Uiso 1 1 d . . . N1 N 1.0084(5) 0.3822(15) 0.3897(10) 0.0362(18) Uiso 1 1 d . . . H1A H 1.0749 0.3057 0.3469 0.054 Uiso 1 1 calc R . . H1B H 1.0337 0.4979 0.4498 0.054 Uiso 1 1 calc R . . O1 O 0.3209(5) 0.3301(13) 0.3656(8) 0.0335(14) Uiso 1 1 d . . . C11 C 0.3276(4) 0.0504(10) 0.1931(7) 0.026(2) Uiso 1 1 d G . . C12 C 0.1944(5) -0.1353(12) 0.2095(6) 0.029(2) Uiso 1 1 d G . . H12 H 0.1619 -0.1645 0.2797 0.034 Uiso 1 1 calc R . . C13 C 0.1097(4) -0.2773(13) 0.1210(7) 0.0236(19) Uiso 1 1 d G . . H13 H 0.0206 -0.4015 0.1319 0.028 Uiso 1 1 calc R . . C14 C 0.1583(5) -0.2336(13) 0.0160(7) 0.027(2) Uiso 1 1 d G . . H14 H 0.1017 -0.3285 -0.0432 0.033 Uiso 1 1 calc R . . C15 C 0.2916(5) -0.0479(13) -0.0003(7) 0.033(2) Uiso 1 1 d G . . H15 H 0.3240 -0.0186 -0.0705 0.040 Uiso 1 1 calc R . . C16 C 0.3762(3) 0.0941(11) 0.0882(7) 0.028(2) Uiso 1 1 d G . . H16 H 0.4654 0.2183 0.0773 0.033 Uiso 1 1 calc R . . C21 C 0.5615(3) 0.2353(11) 0.3123(6) 0.0225(19) Uiso 1 1 d G . . C22 C 0.6635(5) 0.0922(12) 0.2415(6) 0.033(2) Uiso 1 1 d G . . H22 H 0.6313 -0.0317 0.1774 0.040 Uiso 1 1 calc R . . C23 C 0.8138(4) 0.1343(15) 0.2664(6) 0.0292(19) Uiso 1 1 d G . . H23 H 0.8820 0.0386 0.2190 0.035 Uiso 1 1 calc R . . C24 C 0.8620(3) 0.3195(16) 0.3622(6) 0.0286(19) Uiso 1 1 d G . . C25 C 0.7600(5) 0.4626(15) 0.4330(6) 0.031(2) Uiso 1 1 d G . . H25 H 0.7922 0.5864 0.4971 0.037 Uiso 1 1 calc R . . C26 C 0.6098(4) 0.4205(13) 0.4081(6) 0.028(2) Uiso 1 1 d G . . H26 H 0.5415 0.5162 0.4555 0.034 Uiso 1 1 calc R . . _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 O1 1.240(12) . ? C1 C21 1.452(7) . ? C1 C11 1.497(13) . ? N1 C24 1.372(7) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? 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 O1 C1 C21 119.9(10) . . ? O1 C1 C11 116.5(6) . . ? C21 C1 C11 123.6(8) . . ? C12 C11 C16 120.0 . . ? C12 C11 C1 114.0(5) . . ? C16 C11 C1 125.9(5) . . ? C11 C12 C13 120.0 . . ? C14 C13 C12 120.0 . . ? C13 C14 C15 120.0 . . ? C16 C15 C14 120.0 . . ? C15 C16 C11 120.0 . . ? C22 C21 C26 120.0 . . ? C22 C21 C1 124.9(6) . . ? C26 C21 C1 115.1(6) . . ? C23 C22 C21 120.0 . . ? C22 C23 C24 120.0 . . ? N1 C24 C23 122.8(6) . . ? N1 C24 C25 117.1(6) . . ? C23 C24 C25 120.0 . . ? C26 C25 C24 120.0 . . ? C25 C26 C21 120.0 . . ? _diffrn_measured_fraction_theta_max 0.389 _diffrn_reflns_theta_full 23.24 _diffrn_measured_fraction_theta_full 0.389 _refine_diff_density_max 0.144 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.041