#------------------------------------------------------------------------------ #$Date: 2023-01-04 13:34:25 +0000 (Wed, 04 Jan 2023) $ #$Revision: 280099 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519443.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_4519443 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 '0.73(C12 H8 S), 0.27(C12 H8 O)' _chemical_formula_sum 'C12 H8 O0.27 S0.73' _chemical_formula_weight 179.87 _chemical_name_systematic 'dibenzo[b,d]thiophene:dibenzo[b,d]furan 0.73:0.27' _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 2020-12-04 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.9686(3) _cell_length_b 18.8543(6) _cell_length_c 5.8060(2) _cell_measurement_reflns_used 9973 _cell_measurement_temperature 100 _cell_measurement_theta_max 70.062 _cell_measurement_theta_min 4.691 _cell_volume 872.31(5) _computing_cell_refinement ; SAINT (2013) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 3 (2019) 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, 2015b)' _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 1.000 _diffrn_measured_fraction_theta_max 0.994 _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 0.0373 _diffrn_reflns_av_unetI/netI 0.0176 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 16044 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 70.057 _diffrn_reflns_theta_min 4.691 _diffrn_source 'Microfocus Source' _diffrn_source_target Cu _diffrn_source_type 'Incoatec I\mS High Brilliance Microsource' _exptl_absorpt_coefficient_mu 2.193 _exptl_absorpt_correction_T_max 0.3841 _exptl_absorpt_correction_T_min 0.2285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1215 before and 0.0565 after correction. The Ratio of minimum to maximum transmission is 0.5949. 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 1.370 _exptl_crystal_description plate _exptl_crystal_F_000 375 _exptl_crystal_recrystallization_method 'crystallised from MeOH' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.228 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.044 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 68 _refine_ls_number_reflns 843 _refine_ls_number_restraints 12 _refine_ls_restrained_S_all 1.100 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0319 _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^)+(0.0519P)^2^+0.2030P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0855 _refine_ls_wR_factor_ref 0.0857 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 838 _reflns_number_total 843 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 07-73DBT_27DBF.cif _cod_data_source_block jw2251 _cod_database_code 4519443 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 0.80147(17) 0.250000 0.19514(16) 0.0287(3) Uani 0.726(6) 2 d S TU P A 1 O1 O 0.7853(14) 0.250000 0.2402(19) 0.0315(9) Uani 0.274(6) 2 d S TU P A 2 C1 C 0.72681(14) 0.31470(6) 0.3795(2) 0.0325(3) Uani 1 1 d . U . . . C2 C 0.64881(14) 0.28854(6) 0.5788(2) 0.0307(3) Uani 1 1 d . . . . . C3 C 0.58252(15) 0.33660(7) 0.7369(2) 0.0358(3) Uani 1 1 d . . . . . H3 H 0.528848 0.320067 0.872804 0.043 Uiso 1 1 calc R U . . . C4 C 0.59552(17) 0.40841(7) 0.6943(2) 0.0415(4) Uani 1 1 d . . . . . H4 H 0.549908 0.441226 0.801546 0.050 Uiso 1 1 calc R U . . . C5 C 0.67446(16) 0.43342(7) 0.4966(2) 0.0433(4) Uani 1 1 d . . . . . H5 H 0.682351 0.483088 0.471311 0.052 Uiso 1 1 calc R U . . . C6 C 0.74135(17) 0.38736(7) 0.3370(2) 0.0401(3) Uani 1 1 d . . . . . H6 H 0.795646 0.404468 0.202370 0.048 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 0.0336(5) 0.0275(4) 0.0251(5) 0.000 0.0074(3) 0.000 O1 0.0320(14) 0.0340(14) 0.0286(16) 0.000 0.0037(14) 0.000 C1 0.0300(6) 0.0361(7) 0.0315(6) -0.0014(5) -0.0013(5) -0.0008(4) C2 0.0277(6) 0.0325(7) 0.0319(6) 0.0006(4) -0.0013(5) -0.0010(4) C3 0.0326(6) 0.0409(7) 0.0340(6) -0.0037(5) 0.0009(5) 0.0015(5) C4 0.0399(7) 0.0363(7) 0.0484(8) -0.0107(5) -0.0073(5) 0.0049(5) C5 0.0446(7) 0.0307(7) 0.0546(9) 0.0013(6) -0.0131(6) -0.0026(5) C6 0.0391(7) 0.0406(7) 0.0407(7) 0.0090(5) -0.0058(6) -0.0078(6) 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 89.78(9) . 7_565 C1 O1 C1 105.2(6) . 7_565 C2 C1 S1 114.52(9) . . C2 C1 O1 106.8(3) . . C6 C1 S1 123.67(10) . . C6 C1 O1 131.4(3) . . C6 C1 C2 121.81(12) . . C1 C2 C2 69.42(7) . ? C3 C2 C1 118.85(11) . . C3 C2 C2 49.45(7) . ? C2 C3 H3 120.3 . . C4 C3 C2 119.42(12) . . C4 C3 H3 120.3 . . C3 C4 H4 119.5 . . C3 C4 C5 120.95(12) . . C5 C4 H4 119.5 . . C4 C5 H5 119.5 . . C6 C5 C4 121.09(12) . . C6 C5 H5 119.5 . . C1 C6 H6 121.1 . . C5 C6 C1 117.87(12) . . C5 C6 H6 121.1 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C1 1.7286(13) . S1 C1 1.7286(13) 7_565 O1 C1 1.536(6) 7_565 O1 C1 1.536(6) . C1 C2 1.4031(16) . C1 C6 1.3968(18) . C2 C2 10.780(3) ? C2 C3 1.3938(17) . C3 H3 0.9500 . C3 C4 1.3803(18) . C4 H4 0.9500 . C4 C5 1.391(2) . C5 H5 0.9500 . C5 C6 1.377(2) . 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 179.36(10) . . . ? S1 C1 C2 C3 -179.19(10) . . . . S1 C1 C6 C5 179.16(11) . . . . O1 C1 C2 C2 178.9(5) . . . ? O1 C1 C2 C3 -179.6(5) . . . . O1 C1 C6 C5 179.7(6) . . . . C1 S1 C1 C2 0.85(14) 7_565 . . . C1 S1 C1 C6 -179.09(8) 7_565 . . . C1 O1 C1 C2 1.7(7) 7_565 . . . C1 O1 C1 C6 -178.8(2) 7_565 . . . C1 C2 C3 C4 -0.20(17) . . . . C2 C1 C6 C5 -0.78(19) . . . . C2 C2 C3 C4 1.60(8) ? . . . C2 C3 C4 C5 -0.31(19) . . . . C3 C4 C5 C6 0.28(19) . . . . C4 C5 C6 C1 0.26(19) . . . . C6 C1 C2 C2 -0.70(9) . . . ? C6 C1 C2 C3 0.76(17) . . . . _cod_database_fobs_code 4519443