#------------------------------------------------------------------------------ #$Date: 2023-01-04 13:34:40 +0000 (Wed, 04 Jan 2023) $ #$Revision: 280100 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519444.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_4519444 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 '0.79(C12 H8 S), 0.21(C12 H8 O)' _chemical_formula_sum 'C12 H8 O0.21 S0.79' _chemical_formula_weight 180.95 _chemical_name_systematic 'dibenzo[b,d]thiophene:dibenzo[b,d]furan 0.79:0.21' _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 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.0114(7) _cell_length_b 18.8298(16) _cell_length_c 5.8063(5) _cell_measurement_reflns_used 6623 _cell_measurement_temperature 100 _cell_measurement_theta_max 60.584 _cell_measurement_theta_min 6.945 _cell_volume 875.90(13) _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 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.42 _diffrn_detector_type 'Bruker CMOS Photon III ' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Ga K\a' _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_unetI/netI 0.0424 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 8366 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.652 _diffrn_reflns_theta_min 6.943 _diffrn_source 'Metal Jet' _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _exptl_absorpt_coefficient_mu 1.529 _exptl_absorpt_correction_T_max 0.7519 _exptl_absorpt_correction_T_min 0.4623 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1489 before and 0.0878 after correction. The Ratio of minimum to maximum transmission is 0.6148. 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 1.372 _exptl_crystal_description plate _exptl_crystal_F_000 377 _exptl_crystal_recrystallization_method 'crystallized from MeOH' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.252 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 68 _refine_ls_number_reflns 1038 _refine_ls_number_restraints 12 _refine_ls_restrained_S_all 1.098 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0381 _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^)+(0.0537P)^2^+0.2563P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1019 _refine_ls_wR_factor_ref 0.1044 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 949 _reflns_number_total 1038 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 08-79DBT_21DBF.cif _cod_data_source_block jw22612 _cod_database_code 4519444 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 0.80353(15) 0.250000 0.19728(14) 0.0294(3) Uani 0.794(7) 2 d S TU P A 1 O1 O 0.7875(19) 0.250000 0.242(2) 0.0309(9) Uani 0.206(7) 2 d S TU P A 2 C1 C 0.72887(17) 0.31507(7) 0.3805(2) 0.0318(3) Uani 1 1 d . U . . . C2 C 0.65041(16) 0.28855(7) 0.5797(2) 0.0296(3) Uani 1 1 d . . . . . C3 C 0.58358(17) 0.33647(8) 0.7380(2) 0.0348(3) Uani 1 1 d . . . . . H3 H 0.530140 0.319685 0.873517 0.042 Uiso 1 1 calc R U . . . C4 C 0.59563(19) 0.40843(8) 0.6963(2) 0.0405(4) Uani 1 1 d . . . . . H4 H 0.549558 0.441082 0.803581 0.049 Uiso 1 1 calc R U . . . C5 C 0.67452(19) 0.43390(8) 0.4987(3) 0.0422(4) Uani 1 1 d . . . . . H5 H 0.681749 0.483656 0.473623 0.051 Uiso 1 1 calc R U . . . C6 C 0.7423(2) 0.38778(8) 0.3389(2) 0.0386(4) Uani 1 1 d . . . . . H6 H 0.796552 0.405111 0.204710 0.046 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 0.0420(4) 0.0325(4) 0.0137(4) 0.000 0.0067(3) 0.000 O1 0.0401(15) 0.0359(14) 0.0167(15) 0.000 0.0025(14) 0.000 C1 0.0383(6) 0.0381(7) 0.0190(6) -0.0001(5) -0.0012(5) -0.0016(5) C2 0.0356(6) 0.0347(7) 0.0186(5) 0.0004(4) -0.0013(5) -0.0008(5) C3 0.0410(7) 0.0424(7) 0.0211(6) -0.0036(5) 0.0014(5) 0.0015(6) C4 0.0478(8) 0.0396(8) 0.0340(7) -0.0089(5) -0.0048(6) 0.0048(6) C5 0.0525(8) 0.0335(7) 0.0406(8) 0.0009(6) -0.0110(6) -0.0020(6) C6 0.0476(8) 0.0406(8) 0.0276(6) 0.0070(5) -0.0035(6) -0.0059(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.2925 0.4295 '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 90.24(9) . 7_565 C1 O1 C1 105.6(8) . 7_565 C2 C1 S1 114.11(10) . . C2 C1 O1 106.4(4) . . C6 C1 S1 124.24(11) . . C6 C1 O1 131.9(4) . . C6 C1 C2 121.66(12) . . C1 C2 C2 110.77(8) . 7_565 C3 C2 C1 118.90(12) . . C3 C2 C2 130.31(8) . 7_565 C2 C3 H3 120.2 . . C4 C3 C2 119.52(13) . . C4 C3 H3 120.2 . . C3 C4 H4 119.5 . . C3 C4 C5 120.91(13) . . C5 C4 H4 119.5 . . C4 C5 H5 119.5 . . C6 C5 C4 120.95(14) . . C6 C5 H5 119.5 . . C1 C6 H6 121.0 . . C5 C6 C1 118.06(13) . . 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 1.7293(14) . S1 C1 1.7293(14) 7_565 O1 C1 1.539(8) 7_565 O1 C1 1.539(8) . C1 C2 1.4082(17) . C1 C6 1.3943(19) . C2 C2 1.452(3) 7_565 C2 C3 1.3947(18) . C3 H3 0.9500 . C3 C4 1.380(2) . C4 H4 0.9500 . C4 C5 1.395(2) . C5 H5 0.9500 . C5 C6 1.382(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 -0.65(11) . . . 7_565 S1 C1 C2 C3 -179.16(10) . . . . S1 C1 C6 C5 178.97(12) . . . . O1 C1 C2 C2 -1.1(6) . . . 7_565 O1 C1 C2 C3 -179.7(6) . . . . O1 C1 C6 C5 179.6(8) . . . . C1 S1 C1 C2 0.86(14) 7_565 . . . C1 S1 C1 C6 -178.80(9) 7_565 . . . C1 O1 C1 C2 1.8(9) 7_565 . . . C1 O1 C1 C6 -178.4(3) 7_565 . . . C1 C2 C3 C4 0.01(19) . . . . C2 C1 C6 C5 -0.7(2) . . . . C2 C2 C3 C4 -178.16(9) 7_565 . . . C2 C3 C4 C5 -0.4(2) . . . . C3 C4 C5 C6 0.2(2) . . . . C4 C5 C6 C1 0.3(2) . . . . C6 C1 C2 C2 179.02(11) . . . 7_565 C6 C1 C2 C3 0.5(2) . . . . _cod_database_fobs_code 4519444