#------------------------------------------------------------------------------ #$Date: 2023-01-04 13:33:26 +0000 (Wed, 04 Jan 2023) $ #$Revision: 280096 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519440.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_4519440 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 '0.46(C12 H8 S), 0.54(C12 H8 O)' _chemical_formula_sum 'C12 H8 O0.54 S0.46' _chemical_formula_weight 175.49 _chemical_name_systematic 'dibenzo[b,d]thiophene:dibenzo[b,d]furan 0.46:0.54' _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 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.7875(3) _cell_length_b 18.9102(8) _cell_length_c 5.8053(3) _cell_measurement_reflns_used 4331 _cell_measurement_temperature 100 _cell_measurement_theta_max 70.100 _cell_measurement_theta_min 4.677 _cell_volume 854.91(7) _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 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (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 0.999 _diffrn_measured_fraction_theta_max 0.996 _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 0.0334 _diffrn_reflns_av_unetI/netI 0.0210 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _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 -7 _diffrn_reflns_number 7987 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 70.095 _diffrn_reflns_theta_min 4.677 _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 1.643 _exptl_absorpt_correction_T_max 0.7533 _exptl_absorpt_correction_T_min 0.5505 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1138 before and 0.0521 after correction. The Ratio of minimum to maximum transmission is 0.7308. 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 1.363 _exptl_crystal_description plate _exptl_crystal_F_000 367 _exptl_crystal_recrystallization_method 'crystalized from MeOH' _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.204 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.041 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 68 _refine_ls_number_reflns 831 _refine_ls_number_restraints 18 _refine_ls_restrained_S_all 1.131 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0365 _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^)+(0.0584P)^2^+0.2075P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0996 _refine_ls_wR_factor_ref 0.1008 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 796 _reflns_number_total 831 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 04-46DBT_54DBF.cif _cod_data_source_block jw2252 _cod_database_code 4519440 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 0.2134(4) 0.250000 0.1850(4) 0.0305(5) Uani 0.455(6) 2 d S TU P A 1 O1 O 0.2240(10) 0.250000 0.2362(11) 0.0340(9) Uani 0.545(6) 2 d S TU P A 2 C1 C 0.28237(15) 0.31225(7) 0.3721(2) 0.0352(3) Uani 1 1 d . U . . . C2 C 0.36115(14) 0.28861(6) 0.5743(2) 0.0332(3) Uani 1 1 d . . . . . C3 C 0.42357(16) 0.33791(7) 0.7306(2) 0.0383(4) Uani 1 1 d . . . . . H3 H 0.478308 0.323046 0.868651 0.046 Uiso 1 1 calc R U . . . C4 C 0.40458(17) 0.40894(7) 0.6817(3) 0.0457(4) Uani 1 1 d . . . . . H4 H 0.447090 0.443044 0.787460 0.055 Uiso 1 1 calc R U . . . C5 C 0.32455(18) 0.43155(7) 0.4808(3) 0.0488(4) Uani 1 1 d . . . . . H5 H 0.312947 0.480778 0.452206 0.059 Uiso 1 1 calc R U . . . C6 C 0.26176(18) 0.38391(8) 0.3225(3) 0.0459(4) Uani 1 1 d . . . . . H6 H 0.206683 0.399208 0.185279 0.055 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 0.0322(6) 0.0268(6) 0.0326(9) 0.000 -0.0088(6) 0.000 O1 0.0318(13) 0.0335(12) 0.0367(16) 0.000 -0.0050(13) 0.000 C1 0.0283(6) 0.0381(7) 0.0392(6) -0.0018(5) -0.0001(5) 0.0015(5) C2 0.0252(6) 0.0338(7) 0.0407(7) 0.0019(5) -0.0002(5) 0.0014(5) C3 0.0295(6) 0.0428(7) 0.0426(7) -0.0041(5) -0.0014(5) -0.0009(5) C4 0.0362(7) 0.0375(7) 0.0634(9) -0.0125(6) 0.0111(6) -0.0048(6) C5 0.0414(7) 0.0320(7) 0.0730(10) 0.0070(7) 0.0199(7) 0.0061(5) C6 0.0371(7) 0.0492(9) 0.0515(8) 0.0157(6) 0.0089(6) 0.0136(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 88.35(13) 7_565 . C1 O1 C1 104.6(4) 7_565 . C2 C1 S1 117.16(11) . . C2 C1 O1 109.0(2) . . C6 C1 S1 120.53(12) . . C6 C1 O1 128.6(2) . . C6 C1 C2 122.31(13) . . C1 C2 C2 108.65(7) . 7_565 C3 C2 C1 119.18(11) . . C3 C2 C2 132.16(7) . 7_565 C2 C3 H3 120.6 . . C4 C3 C2 118.75(12) . . C4 C3 H3 120.6 . . C3 C4 H4 119.3 . . C3 C4 C5 121.33(13) . . C5 C4 H4 119.3 . . C4 C5 H5 119.4 . . C6 C5 C4 121.21(13) . . C6 C5 H5 119.4 . . C1 C6 H6 121.4 . . C5 C6 C1 117.21(13) . . C5 C6 H6 121.4 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C1 1.689(2) 7_565 S1 C1 1.689(2) . O1 C1 1.488(4) . O1 C1 1.488(4) 7_565 C1 C2 1.3982(17) . C1 C6 1.3944(19) . C2 C2 1.460(2) 7_565 C2 C3 1.3889(17) . C3 H3 0.9500 . C3 C4 1.381(2) . C4 H4 0.9500 . C4 C5 1.390(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 -1.02(15) . . . 7_565 S1 C1 C2 C3 178.47(14) . . . . S1 C1 C6 C5 -178.60(15) . . . . O1 C1 C2 C2 1.5(3) . . . 7_565 O1 C1 C2 C3 -179.0(3) . . . . O1 C1 C6 C5 178.4(4) . . . . C1 S1 C1 C2 1.4(2) 7_565 . . . C1 S1 C1 C6 -179.22(9) 7_565 . . . C1 O1 C1 C2 -2.4(5) 7_565 . . . C1 O1 C1 C6 179.77(16) 7_565 . . . C1 C2 C3 C4 0.46(17) . . . . C2 C1 C6 C5 0.80(19) . . . . C2 C2 C3 C4 179.82(8) 7_565 . . . C2 C3 C4 C5 0.12(19) . . . . C3 C4 C5 C6 -0.3(2) . . . . C4 C5 C6 C1 -0.2(2) . . . . C6 C1 C2 C2 179.56(10) . . . 7_565 C6 C1 C2 C3 -0.95(18) . . . . _cod_database_fobs_code 4519440