#------------------------------------------------------------------------------ #$Date: 2020-05-19 04:37:57 +0300 (Tue, 19 May 2020) $ #$Revision: 252159 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240548.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_7240548 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 C13H9BrN2 _chemical_formula_sum 'C13 H9 Br N2' _chemical_formula_weight 273.13 _chemical_name_common meta-bromo-benzimidazole _chemical_name_systematic 2-(3-bromophenyl)-1H-benzo[d]imidazole _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 direct _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 111.638(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.6755(16) _cell_length_b 9.6559(18) _cell_length_c 9.7645(15) _cell_measurement_reflns_used 10369 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.32 _cell_measurement_theta_min 3.08 _cell_volume 1110.9(3) _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_molecular_graphics 'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.' _computing_publication_material ; MERCURY (Macrae et al., 2006); Platon (Spek, 2009 ; _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-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 R-AXIS-RAPID _diffrn_measurement_method dtprofit.ref _diffrn_radiation_detector RX _diffrn_radiation_monochromator Graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1219 _diffrn_reflns_av_unetI/netI 0.0383 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _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 28474 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.338 _diffrn_reflns_theta_min 3.080 _diffrn_source 'NORMAL-focus sealed tube' _exptl_absorpt_coefficient_mu 3.671 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.3300 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; NUMABS; Higashi, 2002 ; _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'Not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.470 _refine_diff_density_min -0.562 _refine_diff_density_rms 0.104 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 2033 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.1142 _refine_ls_R_factor_gt 0.0832 _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^)+(0.0213P)^2^+7.1057P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1344 _refine_ls_wR_factor_ref 0.1543 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1444 _reflns_number_total 2033 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00410c2.cif _cod_data_source_block shelx_CCDC2 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Numerical' was changed to 'numerical' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240548 _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 0.261 _shelx_estimated_absorpt_t_max 0.838 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL m_Br_benzimidazol New: P21/c CELL 0.71073 12.6755 9.6559 9.7645 90.000 111.638 90.000 ZERR 4.00 0.0016 0.0018 0.0015 0.000 0.009 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H BR N UNIT 52 36 4 8 MERG 2 FMAP 2 PLAN 20 SIZE 0.050 0.100 0.500 ACTA BOND $H CONF L.S. 5 TEMP 20.00 WGHT 0.021300 7.105700 FVAR 1.71223 BR1 3 -0.474109 0.238921 -0.465973 11.00000 0.05555 0.09708 = 0.07674 0.00153 -0.00006 0.01050 N1 4 -0.016441 0.318782 -0.135314 11.00000 0.04950 0.05744 = 0.04193 0.00192 0.01676 0.00058 N2 4 0.005722 0.240722 0.088911 11.00000 0.04854 0.06045 = 0.03314 0.00158 0.01433 -0.00210 AFIX 3 H2N 2 -0.009048 0.198572 0.157351 11.00000 -1.20000 AFIX 0 C1 1 0.102182 0.314712 0.106602 11.00000 0.04255 0.05518 = 0.04514 -0.01385 0.01290 -0.00585 C2 1 0.198714 0.342419 0.226709 11.00000 0.06142 0.05734 = 0.04772 -0.00047 0.01437 -0.00454 AFIX 43 H2 2 0.207529 0.309549 0.319820 11.00000 -1.20000 AFIX 0 C3 1 0.281332 0.419816 0.204934 11.00000 0.05378 0.05997 = 0.05584 -0.00112 0.00790 -0.00620 AFIX 43 H3 2 0.347915 0.438494 0.284504 11.00000 -1.20000 AFIX 0 C4 1 0.268283 0.471538 0.066253 11.00000 0.05323 0.06357 = 0.07518 -0.00447 0.02900 -0.00575 AFIX 43 H4 2 0.325855 0.524554 0.055123 11.00000 -1.20000 AFIX 0 C5 1 0.171165 0.445118 -0.054564 11.00000 0.05749 0.06639 = 0.05337 0.00084 0.01844 -0.00411 AFIX 43 H5 2 0.162530 0.480122 -0.146814 11.00000 -1.20000 AFIX 0 C6 1 0.086718 0.365325 -0.035633 11.00000 0.04904 0.04786 = 0.04719 -0.00835 0.01532 0.00371 C7 1 -0.062352 0.245746 -0.055665 11.00000 0.04132 0.05465 = 0.03547 -0.00227 0.01500 0.00827 C8 1 -0.171418 0.173837 -0.116235 11.00000 0.04662 0.04912 = 0.04563 -0.00946 0.01276 0.00255 C9 1 -0.254985 0.227011 -0.242712 11.00000 0.04696 0.05584 = 0.04413 -0.00041 0.01586 -0.00104 AFIX 43 H9 2 -0.240880 0.305432 -0.288569 11.00000 -1.20000 AFIX 0 C10 1 -0.358896 0.161417 -0.298699 11.00000 0.04676 0.06082 = 0.05027 -0.00555 0.00965 0.00550 C11 1 -0.380166 0.041651 -0.236634 11.00000 0.05430 0.08078 = 0.06049 -0.01046 0.01575 -0.01389 AFIX 43 H11 2 -0.449946 -0.002760 -0.277320 11.00000 -1.20000 AFIX 0 C12 1 -0.295893 -0.011417 -0.112701 11.00000 0.07863 0.06673 = 0.06498 0.00347 0.02601 -0.02354 AFIX 43 H12 2 -0.308963 -0.092497 -0.070030 11.00000 -1.20000 AFIX 0 C13 1 -0.192736 0.054917 -0.051984 11.00000 0.06354 0.06054 = 0.04457 -0.00282 0.00779 -0.00376 AFIX 43 H13 2 -0.137250 0.019509 0.032564 11.00000 -1.20000 AFIX 0 HKLF 4 1.0 -1.00 0.00 -1.00 0.00 1.00 0.00 1.00 0.00 0.00 REM m_Br_benzimidazol New: P21/c REM R1 = 0.0832 for 1444 Fo > 4sig(Fo) and 0.1142 for all 2033 data REM 145 parameters refined using 0 restraints END WGHT 0.0211 7.1056 REM Highest difference peak 0.470, deepest hole -0.562, 1-sigma level 0.104 Q1 1 -0.4741 0.2350 -0.3851 11.00000 0.05 0.47 Q2 1 -0.4247 -0.1552 -0.0542 11.00000 0.05 0.47 Q3 1 -0.5755 0.2478 -0.6099 11.00000 0.05 0.41 Q4 1 -0.5110 0.3032 -0.5051 11.00000 0.05 0.40 Q5 1 0.2159 0.5400 0.0213 11.00000 0.05 0.39 Q6 1 -0.5304 0.1721 -0.5048 11.00000 0.05 0.38 Q7 1 -0.5211 0.4388 -0.4748 11.00000 0.05 0.36 Q8 1 -0.4774 0.3754 -0.3563 11.00000 0.05 0.36 Q9 1 0.0061 0.2283 0.0031 11.00000 0.05 0.36 Q10 1 -0.0429 0.2341 -0.1374 11.00000 0.05 0.35 Q11 1 -0.4853 0.3887 -0.5747 11.00000 0.05 0.35 Q12 1 -0.3853 -0.2168 -0.2524 11.00000 0.05 0.34 Q13 1 -0.4142 0.1775 -0.4419 11.00000 0.05 0.33 Q14 1 -0.3548 0.3160 -0.5093 11.00000 0.05 0.33 Q15 1 -0.4618 0.2882 -0.2777 11.00000 0.05 0.33 Q16 1 -0.4181 0.4020 -0.5025 11.00000 0.05 0.33 Q17 1 0.0759 0.3875 0.0429 11.00000 0.05 0.33 Q18 1 -0.5580 0.2711 -0.3585 11.00000 0.05 0.30 Q19 1 -0.3230 0.1701 -0.3792 11.00000 0.05 0.30 Q20 1 -0.4603 0.0041 -0.1114 11.00000 0.05 0.30 ; _shelx_res_checksum 1443 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 Br1 Br -0.47411(7) 0.23892(11) -0.46597(10) 0.0834(4) Uani 1 1 d . . . . . N1 N -0.0164(5) 0.3188(6) -0.1353(6) 0.0496(14) Uani 1 1 d . . . . . N2 N 0.0057(4) 0.2407(6) 0.0889(5) 0.0476(13) Uani 1 1 d . . . . . H2N H -0.0090 0.1986 0.1574 0.057 Uiso 1 1 d R U . . . C1 C 0.1022(5) 0.3147(7) 0.1066(7) 0.0486(16) Uani 1 1 d . . . . . C2 C 0.1987(6) 0.3424(8) 0.2267(8) 0.0571(19) Uani 1 1 d . . . . . H2 H 0.2075 0.3095 0.3198 0.069 Uiso 1 1 calc R U . . . C3 C 0.2813(6) 0.4198(8) 0.2049(8) 0.0600(19) Uani 1 1 d . . . . . H3 H 0.3479 0.4385 0.2845 0.072 Uiso 1 1 calc R U . . . C4 C 0.2683(6) 0.4715(8) 0.0663(9) 0.062(2) Uani 1 1 d . . . . . H4 H 0.3259 0.5246 0.0551 0.075 Uiso 1 1 calc R U . . . C5 C 0.1712(6) 0.4451(8) -0.0546(8) 0.0596(19) Uani 1 1 d . . . . . H5 H 0.1625 0.4801 -0.1468 0.072 Uiso 1 1 calc R U . . . C6 C 0.0867(6) 0.3653(7) -0.0356(7) 0.0487(16) Uani 1 1 d . . . . . C7 C -0.0624(5) 0.2457(7) -0.0557(6) 0.0436(15) Uani 1 1 d . . . . . C8 C -0.1714(5) 0.1738(7) -0.1162(7) 0.0483(16) Uani 1 1 d . . . . . C9 C -0.2550(5) 0.2270(7) -0.2427(7) 0.0492(16) Uani 1 1 d . . . . . H9 H -0.2409 0.3054 -0.2886 0.059 Uiso 1 1 calc R U . . . C10 C -0.3589(6) 0.1614(8) -0.2987(8) 0.0550(18) Uani 1 1 d . . . . . C11 C -0.3802(7) 0.0417(9) -0.2366(8) 0.067(2) Uani 1 1 d . . . . . H11 H -0.4499 -0.0028 -0.2773 0.080 Uiso 1 1 calc R U . . . C12 C -0.2959(7) -0.0114(9) -0.1127(9) 0.070(2) Uani 1 1 d . . . . . H12 H -0.3090 -0.0925 -0.0700 0.084 Uiso 1 1 calc R U . . . C13 C -0.1927(6) 0.0549(8) -0.0520(7) 0.0597(19) Uani 1 1 d . . . . . H13 H -0.1373 0.0195 0.0326 0.072 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 Br1 0.0555(5) 0.0971(8) 0.0767(6) 0.0015(5) -0.0001(4) 0.0105(5) N1 0.049(3) 0.057(4) 0.042(3) 0.002(3) 0.017(3) 0.001(3) N2 0.049(3) 0.060(4) 0.033(3) 0.002(3) 0.014(2) -0.002(3) C1 0.043(4) 0.055(4) 0.045(4) -0.014(3) 0.013(3) -0.006(3) C2 0.061(5) 0.057(5) 0.048(4) 0.000(3) 0.014(3) -0.005(4) C3 0.054(4) 0.060(5) 0.056(4) -0.001(4) 0.008(3) -0.006(4) C4 0.053(4) 0.064(5) 0.075(5) -0.004(4) 0.029(4) -0.006(4) C5 0.057(5) 0.066(5) 0.053(4) 0.001(4) 0.018(4) -0.004(4) C6 0.049(4) 0.048(4) 0.047(4) -0.008(3) 0.015(3) 0.004(3) C7 0.041(3) 0.055(4) 0.035(3) -0.002(3) 0.015(3) 0.008(3) C8 0.047(4) 0.049(4) 0.046(4) -0.009(3) 0.013(3) 0.003(3) C9 0.047(4) 0.056(4) 0.044(3) 0.000(3) 0.016(3) -0.001(3) C10 0.047(4) 0.061(5) 0.050(4) -0.006(4) 0.010(3) 0.005(4) C11 0.054(5) 0.081(6) 0.060(5) -0.010(4) 0.016(4) -0.014(4) C12 0.079(6) 0.067(5) 0.065(5) 0.003(4) 0.026(4) -0.024(5) C13 0.064(5) 0.061(5) 0.045(4) -0.003(4) 0.008(3) -0.004(4) 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' Br Br -0.2901 2.4595 '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' 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 105.3(5) . . ? C7 N2 C1 107.9(5) . . ? C7 N2 H2N 126.0 . . ? C1 N2 H2N 126.0 . . ? N2 C1 C2 133.0(7) . . ? N2 C1 C6 105.2(5) . . ? C2 C1 C6 121.9(7) . . ? C3 C2 C1 117.8(7) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 121.6(7) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C5 C4 C3 120.9(7) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 118.6(7) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C5 C6 N1 131.4(6) . . ? C5 C6 C1 119.2(6) . . ? N1 C6 C1 109.3(6) . . ? N1 C7 N2 112.3(6) . . ? N1 C7 C8 124.5(5) . . ? N2 C7 C8 123.2(6) . . ? C13 C8 C9 119.7(6) . . ? C13 C8 C7 121.6(6) . . ? C9 C8 C7 118.6(6) . . ? C10 C9 C8 119.0(7) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C11 C10 C9 121.6(7) . . ? C11 C10 Br1 119.8(6) . . ? C9 C10 Br1 118.6(6) . . ? C10 C11 C12 118.8(7) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? C13 C12 C11 120.5(7) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C8 120.3(7) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? 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 C10 1.898(7) . ? N1 C7 1.332(8) . ? N1 C6 1.386(8) . ? N2 C7 1.357(7) . ? N2 C1 1.371(8) . ? N2 H2N 0.8600 . ? C1 C2 1.373(9) . ? C1 C6 1.416(9) . ? C2 C3 1.366(10) . ? C2 H2 0.9300 . ? C3 C4 1.395(10) . ? C3 H3 0.9300 . ? C4 C5 1.379(10) . ? C4 H4 0.9300 . ? C5 C6 1.385(10) . ? C5 H5 0.9300 . ? C7 C8 1.463(9) . ? C8 C13 1.382(10) . ? C8 C9 1.395(9) . ? C9 C10 1.380(9) . ? C9 H9 0.9300 . ? C10 C11 1.378(11) . ? C11 C12 1.384(10) . ? C11 H11 0.9300 . ? C12 C13 1.378(10) . ? C12 H12 0.9300 . ? C13 H13 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 C7 N2 C1 C2 -179.1(8) . . . . ? C7 N2 C1 C6 0.7(7) . . . . ? N2 C1 C2 C3 179.0(7) . . . . ? C6 C1 C2 C3 -0.8(11) . . . . ? C1 C2 C3 C4 1.0(12) . . . . ? C2 C3 C4 C5 -0.5(12) . . . . ? C3 C4 C5 C6 -0.3(12) . . . . ? C4 C5 C6 N1 -177.6(7) . . . . ? C4 C5 C6 C1 0.6(11) . . . . ? C7 N1 C6 C5 179.7(7) . . . . ? C7 N1 C6 C1 1.3(7) . . . . ? N2 C1 C6 C5 -179.8(6) . . . . ? C2 C1 C6 C5 0.0(11) . . . . ? N2 C1 C6 N1 -1.3(8) . . . . ? C2 C1 C6 N1 178.6(6) . . . . ? C6 N1 C7 N2 -0.9(8) . . . . ? C6 N1 C7 C8 -178.6(6) . . . . ? C1 N2 C7 N1 0.1(8) . . . . ? C1 N2 C7 C8 177.8(6) . . . . ? N1 C7 C8 C13 150.1(7) . . . . ? N2 C7 C8 C13 -27.3(10) . . . . ? N1 C7 C8 C9 -29.4(10) . . . . ? N2 C7 C8 C9 153.2(6) . . . . ? C13 C8 C9 C10 1.9(10) . . . . ? C7 C8 C9 C10 -178.7(6) . . . . ? C8 C9 C10 C11 -2.9(11) . . . . ? C8 C9 C10 Br1 177.4(5) . . . . ? C9 C10 C11 C12 1.8(12) . . . . ? Br1 C10 C11 C12 -178.5(6) . . . . ? C10 C11 C12 C13 0.4(12) . . . . ? C11 C12 C13 C8 -1.4(12) . . . . ? C9 C8 C13 C12 0.3(11) . . . . ? C7 C8 C13 C12 -179.2(7) . . . . ?