#------------------------------------------------------------------------------ #$Date: 2020-05-19 04:37:57 +0300 (Tue, 19 May 2020) $ #$Revision: 252159 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240546.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_7240546 loop_ _publ_author_name 'Bombicz, Petra Alexandra' 'May, N\'ora Veronika' 'Fegyverneki, Daniel' 'Saranchimeg, Avirmed' 'Bereczki, Laura' _publ_section_title ; Methods for easy recognition of isostructurality - Lab Jack-like crystal structures of halogenated 2-phenylbenzimidazoles ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00410C _journal_year 2020 _chemical_formula_moiety 'C13 H9 F N2' _chemical_formula_sum 'C13 H9 F N2' _chemical_formula_weight 212.22 _chemical_name_common 2-(2-fluorophenyl)-1H-benzimidazole _chemical_name_systematic 2-(2-fluorophenyl)-1H-benzimidazole _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2020-03-13 deposited with the CCDC. 2020-05-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 7.1246(3) _cell_length_b 10.0327(4) _cell_length_c 29.6291(14) _cell_measurement_reflns_used 13198 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 68.155 _cell_measurement_theta_min 2.985 _cell_volume 2117.86(16) _computing_cell_refinement ; RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)' ; _computing_data_collection ; RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)' ; _computing_data_reduction ; RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)' ; _computing_molecular_graphics 'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.' _computing_publication_material ; C. F. Macrae, J. Appl. Cryst., 41, 466-470, 2008 ; _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type RAXIS-RAPID _diffrn_measurement_method dtprofit.ref _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54187 _diffrn_reflns_av_R_equivalents 0.0553 _diffrn_reflns_av_unetI/netI 0.0454 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 21923 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 67.687 _diffrn_reflns_theta_max 68.219 _diffrn_reflns_theta_min 2.983 _diffrn_source 'Sealed Tube' _exptl_absorpt_coefficient_mu 0.763 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; NUMABS, Numerical Absorption correction Program (T.Higashi, 2011) ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.331 _exptl_crystal_description needle _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.564 _exptl_crystal_size_mid 0.138 _exptl_crystal_size_min 0.061 _exptl_transmission_factor_max 0.99670 _exptl_transmission_factor_min 0.97240 _refine_diff_density_max 0.149 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.032 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.261 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 1924 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.261 _refine_ls_R_factor_all 0.1422 _refine_ls_R_factor_gt 0.0944 _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^)+(0.0403P)^2^+0.9272P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1417 _refine_ls_wR_factor_ref 0.1583 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1343 _reflns_number_total 1924 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00410c2.cif _cod_data_source_block shelx _cod_database_code 7240546 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL Z_THF 08-Aug-2018,11:47: New: Pbca CELL 1.54187 7.1246 10.0327 29.6291 90.000 90.000 90.000 ZERR 8.00 0.0003 0.0004 0.0014 0.000 0.000 0.000 LATT 1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H F N UNIT 104 72 8 16 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF L.S. 5 WGHT 0.040300 0.927200 FVAR 2.24851 F1 3 0.691075 0.182990 0.049910 11.00000 0.13967 0.10665 = 0.09396 0.04422 -0.03176 -0.05382 N1 4 0.738082 -0.121270 0.138439 11.00000 0.05946 0.03149 = 0.06427 0.00477 -0.00204 0.00083 N2 4 0.808288 0.095415 0.134827 11.00000 0.05843 0.03029 = 0.06439 0.00418 -0.00264 -0.00199 C7 1 0.694938 -0.004709 0.120451 11.00000 0.05415 0.03215 = 0.05438 0.00134 0.00313 -0.00230 C6 1 0.887717 -0.094389 0.166828 11.00000 0.05070 0.03529 = 0.05697 0.00329 0.00019 0.00324 C5 1 0.988170 -0.178622 0.195021 11.00000 0.07096 0.04486 = 0.07502 0.00125 -0.00569 0.00526 AFIX 43 H5 2 0.961696 -0.269305 0.196374 11.00000 -1.20000 AFIX 0 C4 1 1.126793 -0.123976 0.220631 11.00000 0.07730 0.05967 = 0.07903 0.00484 -0.00983 0.02065 AFIX 43 H4 2 1.194849 -0.178852 0.239921 11.00000 -1.20000 AFIX 0 C3 1 1.170266 0.011154 0.218960 11.00000 0.06686 0.07551 = 0.07915 -0.00563 -0.01947 0.00176 AFIX 43 H3 2 1.266013 0.044376 0.237087 11.00000 -1.20000 AFIX 0 C2 1 1.074036 0.096286 0.190967 11.00000 0.06498 0.05243 = 0.08295 -0.00466 -0.00667 -0.00698 AFIX 43 H2 2 1.102357 0.186680 0.189565 11.00000 -1.20000 AFIX 0 C1 1 0.932178 0.040554 0.164835 11.00000 0.05119 0.03807 = 0.05767 0.00018 0.00058 0.00198 C8 1 0.533741 0.017325 0.090582 11.00000 0.06016 0.03891 = 0.05783 -0.00253 -0.00388 0.00048 C13 1 0.533014 0.110588 0.056933 11.00000 0.08830 0.05382 = 0.07440 0.00961 -0.02032 -0.01200 C12 1 0.384838 0.135615 0.029240 11.00000 0.13797 0.06786 = 0.09913 0.01094 -0.05109 -0.00270 AFIX 43 H12 2 0.392090 0.199260 0.006486 11.00000 -1.20000 AFIX 0 C11 1 0.223974 0.062921 0.036291 11.00000 0.10158 0.08485 = 0.11539 -0.01410 -0.04879 0.01799 AFIX 43 H11 2 0.119251 0.078986 0.018360 11.00000 -1.20000 AFIX 0 C10 1 0.214932 -0.032095 0.068993 11.00000 0.06567 0.10115 = 0.10043 -0.01652 -0.01506 -0.00754 AFIX 43 H10 2 0.105312 -0.080949 0.073085 11.00000 -1.20000 AFIX 0 C9 1 0.369632 -0.055797 0.096173 11.00000 0.06917 0.07299 = 0.07618 -0.00072 -0.00419 -0.00779 AFIX 43 H9 2 0.363627 -0.121225 0.118361 11.00000 -1.20000 AFIX 0 H2N 2 0.801698 0.183492 0.128637 11.00000 0.07430 HKLF 4 REM Z_THF 08-Aug-2018,11:47: New: Pbca REM R1 = 0.0944 for 1343 Fo > 4sig(Fo) and 0.1422 for all 1924 data REM 149 parameters refined using 0 restraints END WGHT 0.0403 0.9286 REM Highest difference peak 0.149, deepest hole -0.139, 1-sigma level 0.032 Q1 1 0.4486 -0.1671 0.0893 11.00000 0.05 0.11 Q2 1 0.7195 -0.1742 0.1605 11.00000 0.05 0.11 Q3 1 1.2491 0.0266 0.2594 11.00000 0.05 0.11 Q4 1 0.7574 -0.1987 0.1131 11.00000 0.05 0.11 Q5 1 0.7736 -0.0889 0.1192 11.00000 0.05 0.11 Q6 1 0.9755 0.1810 0.0833 11.00000 0.05 0.11 Q7 1 0.5986 -0.1537 0.1319 11.00000 0.05 0.11 Q8 1 0.6331 0.2527 0.1381 11.00000 0.05 0.10 Q9 1 1.1193 -0.2140 0.2597 11.00000 0.05 0.10 Q10 1 0.4865 -0.0716 0.0702 11.00000 0.05 0.10 Q11 1 0.8172 -0.1634 0.1010 11.00000 0.05 0.10 Q12 1 0.2917 0.2211 0.0233 11.00000 0.05 0.09 Q13 1 1.3795 0.0407 0.2004 11.00000 0.05 0.09 Q14 1 0.9790 0.2647 0.1582 11.00000 0.05 0.09 Q15 1 0.4962 -0.2121 0.0705 11.00000 0.05 0.09 Q16 1 0.1735 -0.1489 0.0801 11.00000 0.05 0.09 Q17 1 1.3100 -0.1625 0.2175 11.00000 0.05 0.09 Q18 1 0.6005 0.2020 -0.0193 11.00000 0.05 0.09 Q19 1 0.8870 -0.3084 0.1810 11.00000 0.05 0.09 Q20 1 1.2414 -0.1922 0.2857 11.00000 0.05 0.09 ; _shelx_res_checksum 7861 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -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 F1 F 0.6911(4) 0.1830(3) 0.04991(8) 0.1134(10) Uani 1 1 d . . . . . N1 N 0.7381(4) -0.1213(3) 0.13844(9) 0.0517(7) Uani 1 1 d . . . . . N2 N 0.8083(4) 0.0954(3) 0.13483(10) 0.0510(8) Uani 1 1 d . . . . . C7 C 0.6949(5) -0.0047(3) 0.12045(11) 0.0469(9) Uani 1 1 d . . . . . C6 C 0.8877(5) -0.0944(3) 0.16683(11) 0.0477(9) Uani 1 1 d . . . . . C5 C 0.9882(5) -0.1786(4) 0.19502(13) 0.0636(11) Uani 1 1 d . . . . . H5 H 0.9617 -0.2693 0.1964 0.076 Uiso 1 1 calc R U . . . C4 C 1.1268(6) -0.1240(4) 0.22063(14) 0.0720(12) Uani 1 1 d . . . . . H4 H 1.1948 -0.1789 0.2399 0.086 Uiso 1 1 calc R U . . . C3 C 1.1703(5) 0.0112(4) 0.21896(14) 0.0738(12) Uani 1 1 d . . . . . H3 H 1.2660 0.0444 0.2371 0.089 Uiso 1 1 calc R U . . . C2 C 1.0740(5) 0.0963(4) 0.19097(13) 0.0668(11) Uani 1 1 d . . . . . H2 H 1.1024 0.1867 0.1896 0.080 Uiso 1 1 calc R U . . . C1 C 0.9322(5) 0.0406(3) 0.16483(11) 0.0490(9) Uani 1 1 d . . . . . C8 C 0.5337(5) 0.0173(3) 0.09058(12) 0.0523(9) Uani 1 1 d . . . . . C13 C 0.5330(6) 0.1106(4) 0.05693(14) 0.0722(12) Uani 1 1 d . . . . . C12 C 0.3848(8) 0.1356(5) 0.02924(17) 0.1017(17) Uani 1 1 d . . . . . H12 H 0.3921 0.1993 0.0065 0.122 Uiso 1 1 calc R U . . . C11 C 0.2240(8) 0.0629(5) 0.03629(19) 0.1006(17) Uani 1 1 d . . . . . H11 H 0.1193 0.0790 0.0184 0.121 Uiso 1 1 calc R U . . . C10 C 0.2149(6) -0.0321(5) 0.06899(17) 0.0891(14) Uani 1 1 d . . . . . H10 H 0.1053 -0.0809 0.0731 0.107 Uiso 1 1 calc R U . . . C9 C 0.3696(6) -0.0558(4) 0.09617(14) 0.0728(12) Uani 1 1 d . . . . . H9 H 0.3636 -0.1212 0.1184 0.087 Uiso 1 1 calc R U . . . H2N H 0.802(5) 0.183(4) 0.1286(11) 0.074(13) Uiso 1 1 d . . . . . 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 F1 0.140(2) 0.107(2) 0.0940(18) 0.0442(16) -0.0318(16) -0.0538(19) N1 0.0595(18) 0.0315(16) 0.0643(17) 0.0048(14) -0.0020(16) 0.0008(14) N2 0.0584(19) 0.0303(19) 0.064(2) 0.0042(16) -0.0026(15) -0.0020(15) C7 0.054(2) 0.032(2) 0.054(2) 0.0013(16) 0.0031(17) -0.0023(18) C6 0.051(2) 0.035(2) 0.057(2) 0.0033(17) 0.0002(18) 0.0032(17) C5 0.071(3) 0.045(2) 0.075(3) 0.001(2) -0.006(2) 0.005(2) C4 0.077(3) 0.060(3) 0.079(3) 0.005(2) -0.010(2) 0.021(2) C3 0.067(3) 0.076(3) 0.079(3) -0.006(2) -0.019(2) 0.002(2) C2 0.065(3) 0.052(3) 0.083(3) -0.005(2) -0.007(2) -0.007(2) C1 0.051(2) 0.038(2) 0.058(2) 0.0002(18) 0.0006(18) 0.0020(18) C8 0.060(2) 0.039(2) 0.058(2) -0.0025(18) -0.0039(19) 0.0005(18) C13 0.088(3) 0.054(3) 0.074(3) 0.010(2) -0.020(3) -0.012(2) C12 0.138(5) 0.068(3) 0.099(4) 0.011(3) -0.051(4) -0.003(3) C11 0.102(4) 0.085(4) 0.115(4) -0.014(3) -0.049(4) 0.018(3) C10 0.066(3) 0.101(4) 0.100(3) -0.017(3) -0.015(3) -0.008(3) C9 0.069(3) 0.073(3) 0.076(3) -0.001(2) -0.004(2) -0.008(2) 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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 _geom_angle_publ_flag C7 N1 C6 104.6(3) . . ? C7 N2 C1 106.9(3) . . ? C7 N2 H2N 129(2) . . ? C1 N2 H2N 124(2) . . ? N1 C7 N2 113.0(3) . . ? N1 C7 C8 124.0(3) . . ? N2 C7 C8 122.9(3) . . ? N1 C6 C5 130.1(3) . . ? N1 C6 C1 109.8(3) . . ? C5 C6 C1 120.1(3) . . ? C4 C5 C6 117.7(4) . . ? C4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? C5 C4 C3 122.3(4) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C2 C3 C4 121.1(4) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C2 C1 116.7(4) . . ? C3 C2 H2 121.7 . . ? C1 C2 H2 121.7 . . ? N2 C1 C2 132.0(3) . . ? N2 C1 C6 105.8(3) . . ? C2 C1 C6 122.2(3) . . ? C13 C8 C9 116.4(4) . . ? C13 C8 C7 123.1(3) . . ? C9 C8 C7 120.5(3) . . ? F1 C13 C12 116.9(4) . . ? F1 C13 C8 118.4(4) . . ? C12 C13 C8 124.7(4) . . ? C13 C12 C11 117.2(5) . . ? C13 C12 H12 121.4 . . ? C11 C12 H12 121.4 . . ? C10 C11 C12 121.3(5) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C11 C10 C9 119.8(5) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C9 C8 120.6(4) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C13 1.356(4) . ? N1 C7 1.321(4) . ? N1 C6 1.384(4) . ? N2 C7 1.357(4) . ? N2 C1 1.368(4) . ? N2 H2N 0.90(4) . ? C7 C8 1.467(4) . ? C6 C5 1.387(4) . ? C6 C1 1.392(4) . ? C5 C4 1.361(5) . ? C5 H5 0.9300 . ? C4 C3 1.392(5) . ? C4 H4 0.9300 . ? C3 C2 1.374(5) . ? C3 H3 0.9300 . ? C2 C1 1.391(4) . ? C2 H2 0.9300 . ? C8 C13 1.367(5) . ? C8 C9 1.390(5) . ? C13 C12 1.360(6) . ? C12 C11 1.374(6) . ? C12 H12 0.9300 . ? C11 C10 1.361(6) . ? C11 H11 0.9300 . ? C10 C9 1.386(5) . ? C10 H10 0.9300 . ? C9 H9 0.9300 . ? 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 _geom_torsion_publ_flag C6 N1 C7 N2 0.9(4) . . . . ? C6 N1 C7 C8 -175.0(3) . . . . ? C1 N2 C7 N1 -1.0(4) . . . . ? C1 N2 C7 C8 175.0(3) . . . . ? C7 N1 C6 C5 178.7(3) . . . . ? C7 N1 C6 C1 -0.4(4) . . . . ? N1 C6 C5 C4 -177.9(3) . . . . ? C1 C6 C5 C4 1.1(5) . . . . ? C6 C5 C4 C3 -0.6(6) . . . . ? C5 C4 C3 C2 -0.1(6) . . . . ? C4 C3 C2 C1 0.2(6) . . . . ? C7 N2 C1 C2 -177.4(4) . . . . ? C7 N2 C1 C6 0.7(4) . . . . ? C3 C2 C1 N2 178.2(3) . . . . ? C3 C2 C1 C6 0.4(5) . . . . ? N1 C6 C1 N2 -0.2(4) . . . . ? C5 C6 C1 N2 -179.4(3) . . . . ? N1 C6 C1 C2 178.2(3) . . . . ? C5 C6 C1 C2 -1.1(5) . . . . ? N1 C7 C8 C13 -149.0(4) . . . . ? N2 C7 C8 C13 35.5(5) . . . . ? N1 C7 C8 C9 32.5(5) . . . . ? N2 C7 C8 C9 -143.0(3) . . . . ? C9 C8 C13 F1 -179.1(3) . . . . ? C7 C8 C13 F1 2.3(6) . . . . ? C9 C8 C13 C12 0.0(6) . . . . ? C7 C8 C13 C12 -178.6(4) . . . . ? F1 C13 C12 C11 -179.8(4) . . . . ? C8 C13 C12 C11 1.1(7) . . . . ? C13 C12 C11 C10 -1.4(7) . . . . ? C12 C11 C10 C9 0.6(7) . . . . ? C11 C10 C9 C8 0.5(7) . . . . ? C13 C8 C9 C10 -0.8(6) . . . . ? C7 C8 C9 C10 177.8(3) . . . . ?