#------------------------------------------------------------------------------ #$Date: 2020-05-19 04:37:57 +0300 (Tue, 19 May 2020) $ #$Revision: 252159 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240549.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_7240549 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 Cl N2' _chemical_formula_sum 'C13 H9 Cl N2' _chemical_formula_weight 228.67 _chemical_name_common 2-(3-Chlorophenyl)-1H-benzimidazole _chemical_name_systematic 2-(3-Chlorophenyl)-1H-benzimidazole _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _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 111.933(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.5894(10) _cell_length_b 9.5051(8) _cell_length_c 9.7495(7) _cell_measurement_reflns_used 15162 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.515 _cell_measurement_theta_min 3.110 _cell_volume 1082.22(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 'WinGX publication routines (Farrugia, 2012)' _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 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type RAXIS-RAPID _diffrn_measurement_method dtprofit.ref _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0906 _diffrn_reflns_av_unetI/netI 0.0421 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 19656 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.345 _diffrn_reflns_theta_min 5.238 _diffrn_source 'Sealed Tube' _exptl_absorpt_coefficient_mu 0.322 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.986 _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 1.403 _exptl_crystal_description block _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.830 _exptl_crystal_size_mid 0.311 _exptl_crystal_size_min 0.133 _exptl_transmission_factor_max 0.998395 _exptl_transmission_factor_min 0.985621 _refine_diff_density_max 0.146 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.184 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 1959 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.184 _refine_ls_R_factor_all 0.1044 _refine_ls_R_factor_gt 0.0706 _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^)+(0.0324P)^2^+0.5066P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1056 _refine_ls_wR_factor_ref 0.1155 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1509 _reflns_number_total 1959 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00410c2.cif _cod_data_source_block shelx_CCDC3 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240549 _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_estimated_absorpt_t_min 0.98560 _shelx_estimated_absorpt_t_max 1.00000 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL shelxt_a.res in P-1 New: P21/c CELL 0.71075 12.5894 9.5051 9.7495 90.000 111.933 90.000 ZERR 4.00 0.0010 0.0008 0.0007 0.000 0.008 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H CL N O UNIT 52 36 4 8 0 MERG 2 SHEL 4 0.83 FMAP 2 PLAN 20 ACTA BOND $H CONF L.S. 5 WGHT 0.032400 0.506600 FVAR 2.86194 CL1 3 0.029354 0.270840 0.040162 11.00000 0.05142 0.09329 = 0.06968 0.00119 -0.00325 -0.01280 N2 4 0.503190 0.261042 0.586525 11.00000 0.04590 0.05012 = 0.02567 0.00009 0.01614 0.00553 N1 4 0.480067 0.181098 0.362693 11.00000 0.04430 0.04835 = 0.02966 0.00073 0.01548 0.00300 C7 1 0.434260 0.255098 0.441232 11.00000 0.03878 0.04115 = 0.03055 0.00446 0.01532 0.00012 C6 1 0.584448 0.135061 0.463873 11.00000 0.04212 0.03961 = 0.03266 0.00176 0.01704 -0.00007 C1 1 0.600045 0.184654 0.604544 11.00000 0.04084 0.03749 = 0.03455 0.00372 0.01555 0.00096 C9 1 0.239691 0.274626 0.253299 11.00000 0.04531 0.04631 = 0.03926 0.00442 0.01435 -0.00370 AFIX 43 H9 2 0.254119 0.195860 0.206373 11.00000 -1.20000 AFIX 0 C8 1 0.323528 0.326581 0.381106 11.00000 0.04434 0.04373 = 0.03127 0.00786 0.01658 0.00092 C2 1 0.698725 0.158866 0.725864 11.00000 0.04618 0.04975 = 0.03601 0.00130 0.01073 0.00509 AFIX 43 H2 2 0.708309 0.193032 0.819131 11.00000 -1.20000 AFIX 0 C13 1 0.301191 0.445722 0.447557 11.00000 0.05058 0.06063 = 0.03821 -0.00153 0.01261 0.00631 AFIX 43 H13 2 0.356751 0.481048 0.533379 11.00000 -1.20000 AFIX 0 C5 1 0.669435 0.054436 0.443237 11.00000 0.05339 0.04913 = 0.04210 -0.00397 0.02461 0.00470 AFIX 43 H5 2 0.660134 0.018975 0.350548 11.00000 -1.20000 AFIX 0 C3 1 0.781701 0.080889 0.702792 11.00000 0.04418 0.05230 = 0.05181 0.00555 0.00996 0.00434 AFIX 43 H3 2 0.849536 0.062063 0.781987 11.00000 -1.20000 AFIX 0 C10 1 0.135630 0.340499 0.197098 11.00000 0.04424 0.05976 = 0.04188 0.01113 0.01030 -0.00461 C4 1 0.766907 0.029009 0.563307 11.00000 0.04897 0.05140 = 0.06023 0.00256 0.02535 0.01009 AFIX 43 H4 2 0.824914 -0.024315 0.551679 11.00000 -1.20000 AFIX 0 C11 1 0.112342 0.458814 0.261295 11.00000 0.04525 0.07163 = 0.05973 0.01612 0.01860 0.01800 AFIX 43 H11 2 0.041205 0.502406 0.221302 11.00000 -1.20000 AFIX 0 C12 1 0.196714 0.511833 0.386521 11.00000 0.06404 0.07234 = 0.05303 0.00081 0.01971 0.01985 AFIX 43 H12 2 0.182826 0.593163 0.430175 11.00000 -1.20000 AFIX 0 H2N 2 0.486325 0.287966 0.656027 11.00000 0.03868 HKLF 4 1.0 0.00 0.00 1.00 0.00 -1.00 0.00 1.00 0.00 0.00 REM shelxt_a.res in P-1 New: P21/c REM R1 = 0.0706 for 1509 Fo > 4sig(Fo) and 0.1044 for all 1959 data REM 149 parameters refined using 0 restraints END WGHT 0.0322 0.5096 REM Highest difference peak 0.146, deepest hole -0.186, 1-sigma level 0.036 Q1 1 0.1030 0.2847 0.1345 11.00000 0.05 0.15 Q2 1 0.5241 0.3787 0.6309 11.00000 0.05 0.14 Q3 1 0.1582 0.2538 0.2478 11.00000 0.05 0.14 Q4 1 0.6010 0.0383 0.4544 11.00000 0.05 0.14 Q5 1 0.5837 0.2701 0.6121 11.00000 0.05 0.14 Q6 1 0.4008 0.3259 0.3824 11.00000 0.05 0.14 Q7 1 0.6335 0.1385 0.6735 11.00000 0.05 0.13 Q8 1 0.3657 0.2567 0.4283 11.00000 0.05 0.13 Q9 1 0.8864 0.2275 0.8489 11.00000 0.05 0.12 Q10 1 0.0231 0.1808 0.1069 11.00000 0.05 0.12 Q11 1 0.6255 -0.1119 0.4768 11.00000 0.05 0.12 Q12 1 0.0360 0.0782 -0.0575 11.00000 0.05 0.12 Q13 1 -0.0550 0.2561 -0.0356 11.00000 0.05 0.12 Q14 1 0.8446 0.0142 0.5203 11.00000 0.05 0.11 Q15 1 0.1163 0.5500 0.4631 11.00000 0.05 0.11 Q16 1 0.5384 0.1360 0.5837 11.00000 0.05 0.11 Q17 1 0.2014 0.3460 0.1915 11.00000 0.05 0.11 Q18 1 0.3328 0.4134 0.3863 11.00000 0.05 0.11 Q19 1 0.6534 0.3031 0.5819 11.00000 0.05 0.11 Q20 1 0.1388 0.6857 0.5479 11.00000 0.05 0.11 ; _shelx_res_checksum 93542 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -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 Cl1 Cl 0.02935(7) 0.27084(11) 0.04016(10) 0.0789(4) Uani 1 1 d . . . . . N2 N 0.5032(2) 0.2610(3) 0.5865(2) 0.0398(6) Uani 1 1 d . . . . . N1 N 0.48007(19) 0.1811(3) 0.3627(2) 0.0403(6) Uani 1 1 d . . . . . C7 C 0.4343(2) 0.2551(3) 0.4412(3) 0.0361(6) Uani 1 1 d . . . . . C6 C 0.5844(2) 0.1351(3) 0.4639(3) 0.0372(7) Uani 1 1 d . . . . . C1 C 0.6000(2) 0.1847(3) 0.6045(3) 0.0372(7) Uani 1 1 d . . . . . C9 C 0.2397(2) 0.2746(3) 0.2533(3) 0.0440(7) Uani 1 1 d . . . . . H9 H 0.2541 0.1959 0.2064 0.053 Uiso 1 1 calc R U . . . C8 C 0.3235(2) 0.3266(3) 0.3811(3) 0.0391(7) Uani 1 1 d . . . . . C2 C 0.6987(2) 0.1589(3) 0.7259(3) 0.0453(7) Uani 1 1 d . . . . . H2 H 0.7083 0.1930 0.8191 0.054 Uiso 1 1 calc R U . . . C13 C 0.3012(3) 0.4457(3) 0.4476(3) 0.0510(8) Uani 1 1 d . . . . . H13 H 0.3568 0.4810 0.5334 0.061 Uiso 1 1 calc R U . . . C5 C 0.6694(3) 0.0544(3) 0.4432(3) 0.0462(8) Uani 1 1 d . . . . . H5 H 0.6601 0.0190 0.3505 0.055 Uiso 1 1 calc R U . . . C3 C 0.7817(3) 0.0809(3) 0.7028(3) 0.0517(8) Uani 1 1 d . . . . . H3 H 0.8495 0.0621 0.7820 0.062 Uiso 1 1 calc R U . . . C10 C 0.1356(3) 0.3405(4) 0.1971(3) 0.0503(8) Uani 1 1 d . . . . . C4 C 0.7669(3) 0.0290(3) 0.5633(3) 0.0521(8) Uani 1 1 d . . . . . H4 H 0.8249 -0.0243 0.5517 0.063 Uiso 1 1 calc R U . . . C11 C 0.1123(3) 0.4588(4) 0.2613(4) 0.0592(9) Uani 1 1 d . . . . . H11 H 0.0412 0.5024 0.2213 0.071 Uiso 1 1 calc R U . . . C12 C 0.1967(3) 0.5118(4) 0.3865(4) 0.0638(10) Uani 1 1 d . . . . . H12 H 0.1828 0.5932 0.4302 0.077 Uiso 1 1 calc R U . . . H2N H 0.486(2) 0.288(3) 0.656(3) 0.039(8) 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 Cl1 0.0514(5) 0.0933(8) 0.0697(6) 0.0012(5) -0.0033(4) -0.0128(5) N2 0.0459(14) 0.0501(16) 0.0257(12) 0.0001(11) 0.0161(10) 0.0055(12) N1 0.0443(14) 0.0483(15) 0.0297(12) 0.0007(10) 0.0155(11) 0.0030(11) C7 0.0388(15) 0.0411(17) 0.0305(14) 0.0045(12) 0.0153(11) 0.0001(13) C6 0.0421(17) 0.0396(17) 0.0327(14) 0.0018(12) 0.0170(12) -0.0001(13) C1 0.0408(16) 0.0375(16) 0.0346(15) 0.0037(12) 0.0156(12) 0.0010(13) C9 0.0453(17) 0.0463(18) 0.0393(15) 0.0044(13) 0.0143(13) -0.0037(15) C8 0.0443(17) 0.0437(18) 0.0313(14) 0.0079(13) 0.0166(13) 0.0009(14) C2 0.0462(18) 0.0498(19) 0.0360(15) 0.0013(13) 0.0107(13) 0.0051(15) C13 0.0506(19) 0.061(2) 0.0382(16) -0.0015(15) 0.0126(14) 0.0063(16) C5 0.0534(19) 0.0491(19) 0.0421(16) -0.0040(14) 0.0246(15) 0.0047(15) C3 0.0442(18) 0.052(2) 0.0518(18) 0.0055(15) 0.0100(14) 0.0043(16) C10 0.0442(19) 0.060(2) 0.0419(16) 0.0111(15) 0.0103(14) -0.0046(16) C4 0.0490(19) 0.051(2) 0.060(2) 0.0026(16) 0.0253(16) 0.0101(16) C11 0.0452(19) 0.072(3) 0.060(2) 0.0161(18) 0.0186(16) 0.0180(18) C12 0.064(2) 0.072(3) 0.053(2) 0.0008(17) 0.0197(17) 0.020(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 N2 C1 107.6(2) . . ? C7 N2 H2N 127.7(19) . . ? C1 N2 H2N 123.3(19) . . ? C7 N1 C6 105.0(2) . . ? N1 C7 N2 112.3(2) . . ? N1 C7 C8 124.9(2) . . ? N2 C7 C8 122.7(2) . . ? N1 C6 C5 130.3(2) . . ? N1 C6 C1 110.0(2) . . ? C5 C6 C1 119.7(3) . . ? N2 C1 C2 132.5(3) . . ? N2 C1 C6 105.1(2) . . ? C2 C1 C6 122.3(3) . . ? C10 C9 C8 119.3(3) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C13 C8 C9 119.4(3) . . ? C13 C8 C7 121.5(3) . . ? C9 C8 C7 119.1(3) . . ? C3 C2 C1 117.0(3) . . ? C3 C2 H2 121.5 . . ? C1 C2 H2 121.5 . . ? C12 C13 C8 120.0(3) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? C4 C5 C6 117.9(3) . . ? C4 C5 H5 121.1 . . ? C6 C5 H5 121.1 . . ? C2 C3 C4 121.4(3) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C9 C10 C11 121.9(3) . . ? C9 C10 Cl1 118.9(3) . . ? C11 C10 Cl1 119.2(3) . . ? C5 C4 C3 121.6(3) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C10 C11 C12 118.6(3) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 120.7(3) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? 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 Cl1 C10 1.744(3) . ? N2 C7 1.358(3) . ? N2 C1 1.373(4) . ? N2 H2N 0.82(3) . ? N1 C7 1.320(3) . ? N1 C6 1.387(3) . ? C7 C8 1.462(4) . ? C6 C5 1.390(4) . ? C6 C1 1.393(3) . ? C1 C2 1.380(4) . ? C9 C10 1.368(4) . ? C9 C8 1.389(4) . ? C9 H9 0.9300 . ? C8 C13 1.385(4) . ? C2 C3 1.366(4) . ? C2 H2 0.9300 . ? C13 C12 1.376(4) . ? C13 H13 0.9300 . ? C5 C4 1.364(4) . ? C5 H5 0.9300 . ? C3 C4 1.392(4) . ? C3 H3 0.9300 . ? C10 C11 1.371(5) . ? C4 H4 0.9300 . ? C11 C12 1.380(4) . ? C11 H11 0.9300 . ? C12 H12 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 0.7(3) . . . . ? C6 N1 C7 C8 179.3(3) . . . . ? C1 N2 C7 N1 -0.6(3) . . . . ? C1 N2 C7 C8 -179.2(2) . . . . ? C7 N1 C6 C5 -179.2(3) . . . . ? C7 N1 C6 C1 -0.5(3) . . . . ? C7 N2 C1 C2 177.7(3) . . . . ? C7 N2 C1 C6 0.3(3) . . . . ? N1 C6 C1 N2 0.2(3) . . . . ? C5 C6 C1 N2 179.0(3) . . . . ? N1 C6 C1 C2 -177.6(3) . . . . ? C5 C6 C1 C2 1.2(4) . . . . ? C10 C9 C8 C13 -1.4(4) . . . . ? C10 C9 C8 C7 179.5(2) . . . . ? N1 C7 C8 C13 -151.9(3) . . . . ? N2 C7 C8 C13 26.5(4) . . . . ? N1 C7 C8 C9 27.1(4) . . . . ? N2 C7 C8 C9 -154.5(3) . . . . ? N2 C1 C2 C3 -177.5(3) . . . . ? C6 C1 C2 C3 -0.4(4) . . . . ? C9 C8 C13 C12 -0.2(4) . . . . ? C7 C8 C13 C12 178.8(3) . . . . ? N1 C6 C5 C4 177.4(3) . . . . ? C1 C6 C5 C4 -1.1(4) . . . . ? C1 C2 C3 C4 -0.4(5) . . . . ? C8 C9 C10 C11 1.6(4) . . . . ? C8 C9 C10 Cl1 -177.8(2) . . . . ? C6 C5 C4 C3 0.3(5) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? C9 C10 C11 C12 -0.3(5) . . . . ? Cl1 C10 C11 C12 179.2(2) . . . . ? C8 C13 C12 C11 1.6(5) . . . . ? C10 C11 C12 C13 -1.4(5) . . . . ?