#------------------------------------------------------------------------------ #$Date: 2020-05-19 04:37:57 +0300 (Tue, 19 May 2020) $ #$Revision: 252159 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240547.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_7240547 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 Br N2' _chemical_formula_sum 'C13 H9 Br N2' _chemical_formula_weight 273.13 _chemical_name_common 2-(2-Bromophenyl)-1H-benzimidazole _chemical_name_systematic 2-(2-Bromophenyl)-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 7.007(3) _cell_length_b 9.936(3) _cell_length_c 32.745(3) _cell_measurement_reflns_used 20157 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 68.355 _cell_measurement_theta_min 4.050 _cell_volume 2279.8(12) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type Raxis-Rapid _diffrn_measurement_method dtprofit.ref _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_unetI/netI 0.0664 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _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 39 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_number 23169 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.165 _diffrn_reflns_theta_min 5.403 _diffrn_source 'Sealed Tube' _exptl_absorpt_coefficient_mu 4.675 _exptl_absorpt_correction_T_max 0.916 _exptl_absorpt_correction_T_min 0.839 _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 1.592 _exptl_crystal_description block _exptl_crystal_F_000 1088 _exptl_crystal_size_max 0.411 _exptl_crystal_size_mid 0.346 _exptl_crystal_size_min 0.255 _exptl_transmission_factor_max 0.9158 _exptl_transmission_factor_min 0.839 _refine_diff_density_max 0.589 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.089 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 2078 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.169 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0629 _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^)+(0.0369P)^2^+7.5576P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1377 _refine_ls_wR_factor_ref 0.1418 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1916 _reflns_number_total 2078 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00410c2.cif _cod_data_source_block shelx_CCDC1 _cod_original_cell_volume 2279.76(16) _cod_database_code 7240547 _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 PA-MW05- New: Pbca CELL 1.54178 7.0065 9.9363 32.7453 90.000 90.000 90.000 ZERR 8.00 0.0000 0.0000 0.0000 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 BR N UNIT 104 72 8 16 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF L.S. 5 WGHT 0.036900 7.557600 FVAR 1.02967 BR1 3 0.240805 0.685875 0.051337 11.00000 0.08431 0.05249 = 0.03687 0.01087 0.00497 -0.00600 N1 4 0.255638 0.371057 0.146566 11.00000 0.03249 0.02359 = 0.03324 0.00074 -0.00365 0.00089 N2 4 0.303105 0.592387 0.144247 11.00000 0.03726 0.01361 = 0.03417 0.00265 -0.00228 0.00036 C12 1 -0.281451 0.419565 0.086161 11.00000 0.04133 0.07159 = 0.05641 -0.01925 -0.00990 0.00085 AFIX 43 H12 2 -0.386938 0.367060 0.092745 11.00000 -1.20000 AFIX 0 C8 1 0.037751 0.496488 0.101958 11.00000 0.04107 0.02579 = 0.03424 -0.00698 -0.00255 0.00642 C7 1 0.202205 0.486180 0.130135 11.00000 0.03039 0.02102 = 0.02898 -0.00301 -0.00146 0.00316 C6 1 0.430160 0.542664 0.172722 11.00000 0.03013 0.02137 = 0.03275 -0.00099 0.00289 -0.00113 C2 1 0.506263 0.323635 0.199896 11.00000 0.03656 0.03167 = 0.03330 0.00280 0.00129 0.00692 AFIX 43 H2 2 0.489368 0.230825 0.200548 11.00000 -1.20000 AFIX 0 C3 1 0.636333 0.385502 0.224844 11.00000 0.03249 0.04132 = 0.03310 0.00451 -0.00264 0.01176 AFIX 43 H3 2 0.706615 0.333754 0.243116 11.00000 -1.20000 AFIX 0 C1 1 0.400081 0.404202 0.173513 11.00000 0.03053 0.02625 = 0.02912 0.00083 0.00254 0.00140 C9 1 0.031819 0.576343 0.066855 11.00000 0.05152 0.04048 = 0.03149 -0.00177 -0.00261 0.00983 C4 1 0.665841 0.523808 0.223510 11.00000 0.03082 0.05030 = 0.03715 -0.00809 -0.00505 -0.00308 AFIX 43 H4 2 0.756835 0.561799 0.240675 11.00000 -1.20000 AFIX 0 C5 1 0.564306 0.606555 0.197504 11.00000 0.03299 0.03543 = 0.03966 -0.00516 -0.00040 -0.00731 AFIX 43 H5 2 0.584138 0.699050 0.196575 11.00000 -1.20000 AFIX 0 C13 1 -0.122839 0.418248 0.110683 11.00000 0.04143 0.04889 = 0.04759 -0.00712 -0.00615 0.00027 AFIX 43 H13 2 -0.122131 0.363744 0.133771 11.00000 -1.20000 AFIX 0 C11 1 -0.283607 0.499163 0.051702 11.00000 0.04991 0.09478 = 0.05644 -0.02946 -0.02347 0.02382 AFIX 43 H11 2 -0.390732 0.499815 0.034933 11.00000 -1.20000 AFIX 0 C10 1 -0.128330 0.577736 0.041914 11.00000 0.06984 0.06530 = 0.03741 0.00060 -0.01620 0.02305 AFIX 43 H10 2 -0.130756 0.631534 0.018679 11.00000 -1.20000 AFIX 0 H2N 2 0.284189 0.669280 0.139532 11.00000 0.00708 HKLF 4 REM PA-MW05- New: Pbca REM R1 = 0.0629 for 1916 Fo > 4sig(Fo) and 0.0692 for all 2078 data REM 149 parameters refined using 0 restraints END WGHT 0.0370 7.5537 REM Highest difference peak 0.589, deepest hole -0.602, 1-sigma level 0.089 Q1 1 0.2352 0.6942 0.0843 11.00000 0.05 0.59 Q2 1 0.2247 0.6966 0.0200 11.00000 0.05 0.58 Q3 1 0.3413 0.6259 0.0488 11.00000 0.05 0.58 Q4 1 0.3022 0.6099 0.0448 11.00000 0.05 0.51 Q5 1 0.3503 0.7150 0.0430 11.00000 0.05 0.48 Q6 1 -0.1818 0.3207 0.1245 11.00000 0.05 0.40 Q7 1 0.2358 0.8147 0.0481 11.00000 0.05 0.39 Q8 1 0.2221 0.4301 0.1395 11.00000 0.05 0.33 Q9 1 0.4561 0.5595 0.1931 11.00000 0.05 0.31 Q10 1 0.4332 0.4616 0.1730 11.00000 0.05 0.30 Q11 1 -0.2761 0.5184 0.0704 11.00000 0.05 0.30 Q12 1 0.3043 0.4027 0.1681 11.00000 0.05 0.30 Q13 1 0.1060 0.6217 0.0590 11.00000 0.05 0.30 Q14 1 0.1595 0.3399 0.1494 11.00000 0.05 0.30 Q15 1 0.2428 0.5349 0.1422 11.00000 0.05 0.29 Q16 1 0.4074 0.3699 0.1881 11.00000 0.05 0.28 Q17 1 0.0952 0.5170 0.1271 11.00000 0.05 0.27 Q18 1 -0.1859 0.5223 0.0387 11.00000 0.05 0.26 Q19 1 -0.2314 0.4390 0.0633 11.00000 0.05 0.26 Q20 1 0.3755 0.5669 0.1588 11.00000 0.05 0.25 ; _shelx_res_checksum 20922 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 Br1 Br 0.24081(10) 0.68588(6) 0.05134(2) 0.0579(3) Uani 1 1 d . . . . . N1 N 0.2556(5) 0.3711(4) 0.14657(10) 0.0298(8) Uani 1 1 d . . . . . N2 N 0.3031(5) 0.5924(4) 0.14425(11) 0.0283(8) Uani 1 1 d . . . . . C12 C -0.2815(7) 0.4196(6) 0.08616(18) 0.0564(15) Uani 1 1 d . . . . . H12 H -0.3869 0.3671 0.0927 0.068 Uiso 1 1 calc R U . . . C8 C 0.0378(6) 0.4965(5) 0.10196(13) 0.0337(10) Uani 1 1 d . . . . . C7 C 0.2022(6) 0.4862(4) 0.13013(12) 0.0268(9) Uani 1 1 d . . . . . C6 C 0.4302(6) 0.5427(4) 0.17272(13) 0.0281(9) Uani 1 1 d . . . . . C2 C 0.5063(6) 0.3236(5) 0.19990(13) 0.0338(10) Uani 1 1 d . . . . . H2 H 0.4894 0.2308 0.2005 0.041 Uiso 1 1 calc R U . . . C3 C 0.6363(6) 0.3855(5) 0.22484(13) 0.0356(10) Uani 1 1 d . . . . . H3 H 0.7066 0.3338 0.2431 0.043 Uiso 1 1 calc R U . . . C1 C 0.4001(6) 0.4042(4) 0.17351(12) 0.0286(9) Uani 1 1 d . . . . . C9 C 0.0318(7) 0.5763(5) 0.06685(14) 0.0412(11) Uani 1 1 d . . . . . C4 C 0.6658(6) 0.5238(5) 0.22351(14) 0.0394(11) Uani 1 1 d . . . . . H4 H 0.7568 0.5618 0.2407 0.047 Uiso 1 1 calc R U . . . C5 C 0.5643(6) 0.6066(5) 0.19750(13) 0.0360(10) Uani 1 1 d . . . . . H5 H 0.5841 0.6991 0.1966 0.043 Uiso 1 1 calc R U . . . C13 C -0.1228(7) 0.4182(5) 0.11068(16) 0.0460(12) Uani 1 1 d . . . . . H13 H -0.1221 0.3637 0.1338 0.055 Uiso 1 1 calc R U . . . C11 C -0.2836(8) 0.4992(8) 0.05170(18) 0.0670(19) Uani 1 1 d . . . . . H11 H -0.3907 0.4998 0.0349 0.080 Uiso 1 1 calc R U . . . C10 C -0.1283(9) 0.5777(6) 0.04191(16) 0.0575(16) Uani 1 1 d . . . . . H10 H -0.1308 0.6315 0.0187 0.069 Uiso 1 1 calc R U . . . H2N H 0.284(5) 0.669(4) 0.1395(11) 0.007(10) 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 Br1 0.0843(5) 0.0525(4) 0.0369(3) 0.0109(2) 0.0050(3) -0.0060(3) N1 0.0325(17) 0.0236(19) 0.0332(18) 0.0007(15) -0.0036(15) 0.0009(15) N2 0.0373(19) 0.014(2) 0.0342(19) 0.0026(15) -0.0023(15) 0.0004(15) C12 0.041(3) 0.072(4) 0.056(3) -0.019(3) -0.010(2) 0.001(3) C8 0.041(2) 0.026(2) 0.034(2) -0.0070(19) -0.0026(19) 0.0064(19) C7 0.030(2) 0.021(2) 0.029(2) -0.0030(17) -0.0015(16) 0.0032(17) C6 0.030(2) 0.021(2) 0.033(2) -0.0010(17) 0.0029(17) -0.0011(17) C2 0.037(2) 0.032(3) 0.033(2) 0.0028(19) 0.0013(19) 0.007(2) C3 0.032(2) 0.041(3) 0.033(2) 0.005(2) -0.0026(18) 0.012(2) C1 0.031(2) 0.026(2) 0.029(2) 0.0008(17) 0.0025(17) 0.0014(18) C9 0.052(3) 0.040(3) 0.031(2) -0.002(2) -0.003(2) 0.010(2) C4 0.031(2) 0.050(3) 0.037(2) -0.008(2) -0.0051(19) -0.003(2) C5 0.033(2) 0.035(3) 0.040(2) -0.005(2) -0.0004(19) -0.007(2) C13 0.041(3) 0.049(3) 0.048(3) -0.007(2) -0.006(2) 0.000(2) C11 0.050(3) 0.095(5) 0.056(4) -0.029(3) -0.023(3) 0.024(3) C10 0.070(4) 0.065(4) 0.037(3) 0.001(3) -0.016(3) 0.023(3) 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' Br Br -0.6763 1.2805 '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 C1 105.2(3) . . ? C7 N2 C6 106.8(4) . . ? C7 N2 H2N 127(3) . . ? C6 N2 H2N 126(3) . . ? C13 C12 C11 119.6(6) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C13 C8 C9 117.4(4) . . ? C13 C8 C7 117.5(4) . . ? C9 C8 C7 125.1(4) . . ? N1 C7 N2 112.9(4) . . ? N1 C7 C8 122.4(4) . . ? N2 C7 C8 124.5(4) . . ? N2 C6 C1 105.6(4) . . ? N2 C6 C5 131.7(4) . . ? C1 C6 C5 122.8(4) . . ? C3 C2 C1 117.9(4) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 121.6(4) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? N1 C1 C6 109.5(4) . . ? N1 C1 C2 130.5(4) . . ? C6 C1 C2 119.9(4) . . ? C10 C9 C8 120.9(5) . . ? C10 C9 Br1 117.5(4) . . ? C8 C9 Br1 121.6(4) . . ? C5 C4 C3 122.1(4) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C6 115.8(4) . . ? C4 C5 H5 122.1 . . ? C6 C5 H5 122.1 . . ? C12 C13 C8 121.8(5) . . ? C12 C13 H13 119.1 . . ? C8 C13 H13 119.1 . . ? C10 C11 C12 120.5(5) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C10 C9 119.7(5) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? 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 Br1 C9 1.894(5) . ? N1 C7 1.318(6) . ? N1 C1 1.382(5) . ? N2 C7 1.352(6) . ? N2 C6 1.381(5) . ? N2 H2N 0.79(4) . ? C12 C13 1.371(7) . ? C12 C11 1.378(9) . ? C12 H12 0.9300 . ? C8 C13 1.397(7) . ? C8 C9 1.397(6) . ? C8 C7 1.480(6) . ? C6 C1 1.392(6) . ? C6 C5 1.395(6) . ? C2 C3 1.370(6) . ? C2 C1 1.393(6) . ? C2 H2 0.9300 . ? C3 C4 1.390(7) . ? C3 H3 0.9300 . ? C9 C10 1.388(7) . ? C4 C5 1.381(7) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C13 H13 0.9300 . ? C11 C10 1.377(10) . ? C11 H11 0.9300 . ? C10 H10 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 C1 N1 C7 N2 0.5(5) . . . . ? C1 N1 C7 C8 -174.6(4) . . . . ? C6 N2 C7 N1 -1.2(5) . . . . ? C6 N2 C7 C8 173.9(4) . . . . ? C13 C8 C7 N1 38.7(6) . . . . ? C9 C8 C7 N1 -139.9(5) . . . . ? C13 C8 C7 N2 -135.8(5) . . . . ? C9 C8 C7 N2 45.5(6) . . . . ? C7 N2 C6 C1 1.2(4) . . . . ? C7 N2 C6 C5 -178.0(4) . . . . ? C1 C2 C3 C4 -1.4(6) . . . . ? C7 N1 C1 C6 0.3(5) . . . . ? C7 N1 C1 C2 178.4(4) . . . . ? N2 C6 C1 N1 -1.0(5) . . . . ? C5 C6 C1 N1 178.4(4) . . . . ? N2 C6 C1 C2 -179.3(4) . . . . ? C5 C6 C1 C2 0.1(6) . . . . ? C3 C2 C1 N1 -177.0(4) . . . . ? C3 C2 C1 C6 0.9(6) . . . . ? C13 C8 C9 C10 0.3(7) . . . . ? C7 C8 C9 C10 179.0(5) . . . . ? C13 C8 C9 Br1 -179.5(4) . . . . ? C7 C8 C9 Br1 -0.8(6) . . . . ? C2 C3 C4 C5 0.9(7) . . . . ? C3 C4 C5 C6 0.1(7) . . . . ? N2 C6 C5 C4 178.6(4) . . . . ? C1 C6 C5 C4 -0.6(6) . . . . ? C11 C12 C13 C8 0.5(8) . . . . ? C9 C8 C13 C12 -0.4(7) . . . . ? C7 C8 C13 C12 -179.2(4) . . . . ? C13 C12 C11 C10 -0.4(9) . . . . ? C12 C11 C10 C9 0.3(9) . . . . ? C8 C9 C10 C11 -0.2(8) . . . . ? Br1 C9 C10 C11 179.6(4) . . . . ?