#------------------------------------------------------------------------------ #$Date: 2023-01-04 13:33:13 +0000 (Wed, 04 Jan 2023) $ #$Revision: 280095 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519439.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_4519439 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 '0.69(C13 H10), 0.31(C12 H8 O)' _chemical_formula_sum 'C12.69 H9.37 O0.31' _chemical_formula_weight 166.83 _chemical_name_systematic '9H-fluorene:dibenzo[b,d]furan 0.69:0.31' _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 8.0978(3) _cell_length_b 18.8577(8) _cell_length_c 5.7063(2) _cell_measurement_reflns_used 5134 _cell_measurement_temperature 100 _cell_measurement_theta_max 71.637 _cell_measurement_theta_min 2.343 _cell_volume 871.39(6) _computing_cell_refinement ; SAINT (2020) 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 (2020) 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 100.15 _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 0.993 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_unetI/netI 0.0129 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.993 _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 10615 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 72.049 _diffrn_reflns_theta_min 4.690 _exptl_absorpt_coefficient_mu 0.570 _exptl_absorpt_correction_T_max 0.5229 _exptl_absorpt_correction_T_min 0.4123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1553 before and 0.0417 after correction. The Ratio of minimum to maximum transmission is 0.7885. 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 1.272 _exptl_crystal_description Plate _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.350 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 871 _refine_ls_number_restraints 188 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0558 _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^)+(0.0849P)^2^+0.7230P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1550 _refine_ls_wR_factor_ref 0.1578 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 816 _reflns_number_total 871 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 03-31DBF_69FLU.cif _cod_data_source_block dbflu _cod_database_code 4519439 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 C1A C 0.72499(17) 0.31053(6) 0.6273(2) 0.0290(5) Uani 0.908(3) 1 d G U P A 1 C2A C 0.63932(18) 0.28874(5) 0.4289(3) 0.0273(5) Uani 0.908(3) 1 d G U P A 1 C3A C 0.57300(16) 0.33884(9) 0.27709(19) 0.0309(5) Uani 0.908(3) 1 d G U P A 1 H3A H 0.514478 0.323956 0.141442 0.037 Uiso 0.908(3) 1 calc R U P A 1 C4A C 0.59227(18) 0.41070(7) 0.3236(2) 0.0348(5) Uani 0.908(3) 1 d G U P A 1 H4A H 0.546898 0.444942 0.219882 0.042 Uiso 0.908(3) 1 calc R U P A 1 C5A C 0.67795(19) 0.43245(4) 0.5221(3) 0.0349(5) Uani 0.908(3) 1 d G U P A 1 H5A H 0.691164 0.481571 0.553923 0.042 Uiso 0.908(3) 1 calc R U P A 1 C6A C 0.74430(16) 0.38237(8) 0.67394(19) 0.0329(5) Uani 0.908(3) 1 d G U P A 1 H6A H 0.802847 0.397253 0.809565 0.040 Uiso 0.908(3) 1 calc R U P A 1 C7A C 0.7942(8) 0.250000 0.7559(14) 0.0299(7) Uani 0.684(17) 2 d S TU P A 1 H7AA H 0.758044 0.250000 0.921591 0.036 Uiso 0.684(17) 2 calc R U P A 1 H7AB H 0.916410 0.250000 0.749781 0.036 Uiso 0.684(17) 2 calc R U P A 1 O1A O 0.7676(15) 0.250000 0.770(3) 0.0292(7) Uani 0.253(13) 2 d S TU P A 2 O1B O 0.543(3) 0.250000 0.221(3) 0.0292(7) Uani 0.063(3) 2 d DS TU P A 3 C1B C 0.6040(18) 0.3050(7) 0.353(2) 0.0296(7) Uani 0.092(3) 1 d DG U P A 3 C2B C 0.6919(19) 0.28873(6) 0.555(3) 0.0295(7) Uani 0.092(3) 1 d DG U P A 3 C3B C 0.7547(16) 0.3429(5) 0.6947(19) 0.0313(8) Uani 0.092(3) 1 d G U P A 3 H3B H 0.814710 0.331773 0.832936 0.038 Uiso 0.092(3) 1 calc R U P A 3 C4B C 0.7296(18) 0.4133(3) 0.632(2) 0.0332(8) Uani 0.092(3) 1 d G U P A 3 H4B H 0.772469 0.450254 0.726841 0.040 Uiso 0.092(3) 1 calc R U P A 3 C5B C 0.6417(19) 0.4295(4) 0.429(3) 0.0337(8) Uani 0.092(3) 1 d G U P A 3 H5B H 0.624542 0.477591 0.386356 0.040 Uiso 0.092(3) 1 calc R U P A 3 C6B C 0.5789(17) 0.3753(10) 0.2902(19) 0.0322(8) Uani 0.092(3) 1 d G U P A 3 H6B H 0.518856 0.386447 0.151963 0.039 Uiso 0.092(3) 1 calc R U P A 3 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 C1A 0.0320(8) 0.0306(9) 0.0244(8) -0.0011(6) 0.0011(6) -0.0012(6) C2A 0.0291(8) 0.0304(9) 0.0223(8) -0.0001(6) -0.0002(6) -0.0002(6) C3A 0.0345(8) 0.0307(9) 0.0275(8) 0.0024(7) -0.0009(6) 0.0005(7) C4A 0.0392(9) 0.0307(9) 0.0343(9) 0.0036(7) 0.0036(7) 0.0009(7) C5A 0.0411(9) 0.0289(8) 0.0348(10) -0.0011(7) 0.0048(8) -0.0021(7) C6A 0.0386(9) 0.0297(9) 0.0305(8) -0.0029(7) 0.0030(7) -0.0027(7) C7A 0.0321(14) 0.0331(11) 0.0244(12) 0.000 -0.0005(12) 0.000 O1A 0.0316(12) 0.0318(11) 0.0243(12) 0.000 -0.0002(11) 0.000 O1B 0.0316(12) 0.0318(11) 0.0243(12) 0.000 -0.0002(11) 0.000 C1B 0.0328(12) 0.0303(12) 0.0258(12) 0.0007(10) 0.0002(11) -0.0002(10) C2B 0.0323(12) 0.0314(11) 0.0249(11) -0.0003(9) 0.0002(10) -0.0006(9) C3B 0.0355(13) 0.0302(13) 0.0280(13) -0.0007(12) 0.0021(12) -0.0011(12) C4B 0.0387(13) 0.0291(13) 0.0317(13) -0.0018(12) 0.0035(12) -0.0021(12) C5B 0.0390(13) 0.0297(13) 0.0324(13) 0.0006(12) 0.0031(12) -0.0010(12) C6B 0.0365(13) 0.0301(14) 0.0301(13) 0.0021(12) 0.0014(12) 0.0001(12) 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' 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 C2A C1A C7A 111.6(3) . . C6A C1A C2A 120.0 . . C6A C1A C7A 128.3(3) . . C1A C2A C2A 107.2 . 7_565 C1A C2A C3A 120.0 . . C3A C2A C2A 132.8 . 7_565 C2A C3A H3A 120.0 . . C4A C3A C2A 120.0 . . C4A C3A H3A 120.0 . . C3A C4A H4A 120.0 . . C3A C4A C5A 120.0 . . C5A C4A H4A 120.0 . . C4A C5A H5A 120.0 . . C6A C5A C4A 120.0 . . C6A C5A H5A 120.0 . . C1A C6A C5A 120.0 . . C1A C6A H6A 120.0 . . C5A C6A H6A 120.0 . . C1A C7A C1A 102.1(5) . 7_565 C1A C7A H7AA 111.4 7_565 . C1A C7A H7AA 111.4 . . C1A C7A H7AB 111.4 . . C1A C7A H7AB 111.4 7_565 . H7AA C7A H7AB 109.2 . . O1B C1B C2B 118.3(15) . . O1B C1B C6B 121.7(15) . . C2B C1B C6B 120.0 . . C1B C2B C3B 120.0 . . C2B C3B H3B 120.0 . . C4B C3B C2B 120.0 . . C4B C3B H3B 120.0 . . C3B C4B H4B 120.0 . . C3B C4B C5B 120.0 . . C5B C4B H4B 120.0 . . C4B C5B H5B 120.0 . . C6B C5B C4B 120.0 . . C6B C5B H5B 120.0 . . C1B C6B H6B 120.0 . . C5B C6B C1B 120.0 . . C5B C6B H6B 120.0 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1A C2A 1.3899 . C1A C6A 1.3894 . C1A C7A 1.468(5) . C2A C2A 1.4611(17) 7_565 C2A C3A 1.3899 . C3A H3A 0.9500 . C3A C4A 1.3897 . C4A H4A 0.9500 . C4A C5A 1.3899 . C5A H5A 0.9500 . C5A C6A 1.3898 . C6A H6A 0.9500 . C7A H7AA 0.9900 . C7A H7AB 0.9900 . O1B C1B 1.374(5) . O1B C1B 1.374(5) 7_565 C1B C2B 1.3900 . C1B C6B 1.3900 . C2B C2B 1.461(2) 7_565 C2B C3B 1.3900 . C3B H3B 0.9500 . C3B C4B 1.3900 . C4B H4B 0.9500 . C4B C5B 1.3900 . C5B H5B 0.9500 . C5B C6B 1.3900 . C6B H6B 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 C1A C2A C3A C4A 0.0 . . . . C2A C1A C6A C5A 0.0 . . . . C2A C1A C7A C1A -6.1(5) . . . 7_565 C2A C2A C3A C4A 179.7 7_565 . . . C2A C3A C4A C5A 0.0 . . . . C3A C4A C5A C6A 0.0 . . . . C4A C5A C6A C1A 0.0 . . . . C6A C1A C2A C2A -179.7 . . . 7_565 C6A C1A C2A C3A 0.0 . . . . C6A C1A C7A C1A 178.04(13) . . . 7_565 C7A C1A C2A C2A 4.0(3) . . . 7_565 C7A C1A C2A C3A -176.3(3) . . . . C7A C1A C6A C5A 175.6(4) . . . . O1B C1B C2B C2B 1.0(17) . . . 7_565 O1B C1B C2B C3B -179.7(17) . . . . O1B C1B C6B C5B 179.7(17) . . . . C1B O1B C1B C2B -2(2) 7_565 . . . C1B O1B C1B C6B 178.7(8) 7_565 . . . C1B C2B C3B C4B 0.0 . . . . C2B C1B C6B C5B 0.0 . . . . C2B C2B C3B C4B 178.9 7_565 . . . C2B C3B C4B C5B 0.0 . . . . C3B C4B C5B C6B 0.0 . . . . C4B C5B C6B C1B 0.0 . . . . C6B C1B C2B C2B -179.2 . . . 7_565 C6B C1B C2B C3B 0.0 . . . . _cod_database_fobs_code 4519439