#------------------------------------------------------------------------------ #$Date: 2023-01-04 13:33:41 +0000 (Wed, 04 Jan 2023) $ #$Revision: 280097 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519441.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4519441 loop_ _publ_author_name 'Norbert M. Villeneuve' 'Joshua Dickman' 'Thierry Maris' 'Graeme M. Day' 'James D. Wuest' _publ_section_title ; Seeking Rules Governing Mixed Molecular Crystallization ; _journal_name_full 'Crystal Growth & Design' _journal_page_first 273 _journal_page_last 288 _journal_paper_doi 10.1021/acs.cgd.2c00992 _journal_volume 23 _journal_year 2023 _chemical_formula_moiety '0.59(C12 H8 S), 0.41(C12 H8 O)' _chemical_formula_sum 'C12 H8 O0.41 S0.59' _chemical_formula_weight 177.66 _chemical_name_systematic 'dibenzo[b,d]thiophene:dibenzo[b,d]furan 0.59:0.41' _space_group_crystal_system orthorhombic _space_group_IT_number 62 _space_group_name_Hall '-P 2ac 2n' _space_group_name_H-M_alt 'P n m a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-11-17 _audit_creation_method ; Olex2 1.3 (compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.8867(5) _cell_length_b 18.8866(12) _cell_length_c 5.8042(4) _cell_measurement_reflns_used 2171 _cell_measurement_temperature 100 _cell_measurement_theta_max 69.866 _cell_measurement_theta_min 4.683 _cell_volume 864.55(10) _computing_cell_refinement ; SAINT (2013) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2013) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2005b)' _computing_structure_solution 'XT (Sheldrick, 2015a)' _diffrn_ambient_temperature 100 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 8.3 _diffrn_detector_type 'Bruker APEX2 CCD' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method '\w scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Quazar MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_unetI/netI 0.0313 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 5348 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 69.860 _diffrn_reflns_theta_min 4.682 _diffrn_source 'Microfocus Source' _diffrn_source_current 0.65 _diffrn_source_power 0.02912 _diffrn_source_target Cu _diffrn_source_type 'Incoatec I\mS High Brilliance Microsource' _diffrn_source_voltage 44.8 _exptl_absorpt_coefficient_mu 1.916 _exptl_absorpt_correction_T_max 0.7533 _exptl_absorpt_correction_T_min 0.5364 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1471 before and 0.0621 after correction. The Ratio of minimum to maximum transmission is 0.7121. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.365 _exptl_crystal_description plate _exptl_crystal_F_000 371 _exptl_crystal_recrystallization_method 'crystallized from EtOH' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.295 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.042 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 68 _refine_ls_number_reflns 835 _refine_ls_number_restraints 12 _refine_ls_restrained_S_all 1.079 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0388 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.1670P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1065 _refine_ls_wR_factor_ref 0.1091 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 778 _reflns_number_total 835 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 05-59DBT_41DBF.cif _cod_data_source_block jw22472 _cod_database_code 4519441 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z' 4 'x+1/2, -y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 'x, -y-1/2, z' 8 '-x-1/2, y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.7959(3) 0.250000 0.1911(4) 0.0319(4) Uani 0.591(7) 2 d S TU P A 1 O1 O 0.7771(14) 0.250000 0.2393(17) 0.0395(19) Uani 0.409(7) 2 d S TU P A 2 C1 C 0.72246(17) 0.31361(8) 0.3757(2) 0.0385(4) Uani 1 1 d . U . . . C2 C 0.64432(16) 0.28850(7) 0.5769(2) 0.0361(4) Uani 1 1 d . . . . . C3 C 0.57968(19) 0.33727(8) 0.7339(3) 0.0414(4) Uani 1 1 d . . . . . H3 H 0.525328 0.321524 0.870684 0.050 Uiso 1 1 calc R U . . . C4 C 0.5953(2) 0.40856(8) 0.6889(3) 0.0481(5) Uani 1 1 d . . . . . H4 H 0.551140 0.441865 0.795834 0.058 Uiso 1 1 calc R U . . . C5 C 0.6746(2) 0.43272(9) 0.4900(3) 0.0506(5) Uani 1 1 d . . . . . H5 H 0.684135 0.482191 0.463360 0.061 Uiso 1 1 calc R U . . . C6 C 0.7394(2) 0.38592(9) 0.3311(3) 0.0477(4) Uani 1 1 d . . . . . H6 H 0.793898 0.402289 0.195209 0.057 Uiso 1 1 calc R U . . . 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 S1 0.0368(7) 0.0295(6) 0.0295(8) 0.000 0.0098(5) 0.000 O1 0.037(3) 0.046(3) 0.035(3) 0.000 0.008(2) 0.000 C1 0.0341(7) 0.0440(9) 0.0373(7) -0.0010(6) -0.0011(6) -0.0021(5) C2 0.0323(7) 0.0384(9) 0.0375(7) 0.0009(5) -0.0002(6) -0.0016(5) C3 0.0369(7) 0.0467(9) 0.0404(7) -0.0040(6) 0.0015(6) 0.0017(6) C4 0.0445(9) 0.0422(9) 0.0576(10) -0.0113(7) -0.0101(7) 0.0052(6) C5 0.0502(9) 0.0347(8) 0.0670(11) 0.0042(7) -0.0179(8) -0.0047(6) C6 0.0441(8) 0.0508(10) 0.0482(8) 0.0127(7) -0.0085(7) -0.0108(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C1 S1 C1 89.24(15) . 7_565 C1 O1 C1 106.3(6) . 7_565 C2 C1 S1 115.62(13) . . C2 C1 O1 107.1(3) . . C6 C1 S1 122.59(14) . . C6 C1 O1 131.1(3) . . C6 C1 C2 121.79(14) . . C1 C2 C2 109.76(9) . 7_565 C3 C2 C1 118.82(14) . . C3 C2 C2 131.41(9) . 7_565 C2 C3 H3 120.3 . . C4 C3 C2 119.32(14) . . C4 C3 H3 120.3 . . C3 C4 H4 119.4 . . C3 C4 C5 121.26(15) . . C5 C4 H4 119.4 . . C4 C5 H5 119.6 . . C6 C5 C4 120.85(15) . . C6 C5 H5 119.6 . . C1 C6 H6 121.0 . . C5 C6 C1 117.95(15) . . C5 C6 H6 121.0 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C1 1.711(2) . S1 C1 1.711(2) 7_565 O1 C1 1.502(6) 7_565 O1 C1 1.502(6) . C1 C2 1.403(2) . C1 C6 1.396(2) . C2 C2 1.454(3) 7_565 C2 C3 1.393(2) . C3 H3 0.9500 . C3 C4 1.377(2) . C4 H4 0.9500 . C4 C5 1.390(2) . C5 H5 0.9500 . C5 C6 1.376(3) . C6 H6 0.9500 . 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 S1 C1 C2 C2 -0.45(15) . . . 7_565 S1 C1 C2 C3 -179.25(15) . . . . S1 C1 C6 C5 179.46(16) . . . . O1 C1 C2 C2 -0.5(5) . . . 7_565 O1 C1 C2 C3 -179.3(5) . . . . O1 C1 C6 C5 179.6(6) . . . . C1 S1 C1 C2 0.6(2) 7_565 . . . C1 S1 C1 C6 -179.72(10) 7_565 . . . C1 O1 C1 C2 0.8(7) 7_565 . . . C1 O1 C1 C6 -179.6(2) 7_565 . . . C1 C2 C3 C4 -0.6(2) . . . . C2 C1 C6 C5 -0.9(2) . . . . C2 C2 C3 C4 -179.06(9) 7_565 . . . C2 C3 C4 C5 -0.1(2) . . . . C3 C4 C5 C6 0.3(2) . . . . C4 C5 C6 C1 0.2(2) . . . . C6 C1 C2 C2 179.86(11) . . . 7_565 C6 C1 C2 C3 1.1(2) . . . . _cod_database_fobs_code 4519441