#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/51/2005184.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2005184 loop_ _publ_author_name 'Panneerselvam, K.' 'Soriano-Garc\'ia, M.' _publ_section_title ; 2-Chlorobenzimidazole ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1799 _journal_page_last 1801 _journal_paper_doi 10.1107/S0108270195017203 _journal_volume 52 _journal_year 1996 _chemical_formula_structural 'C7 H5 Cl1 N2' _chemical_formula_sum 'C7 H5 Cl N2' _chemical_formula_weight 152.58 _chemical_name_common 2-chlorobenzimidazole _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 9.937(4) _cell_length_b 9.192(1) _cell_length_c 14.417(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 45 _cell_measurement_theta_min 15 _cell_volume 1316.9(6) _computing_cell_refinement 'XSCANS (Siemens, 1991)' _computing_data_collection 'P4 diffractometer software' _computing_data_reduction XSCANS _computing_molecular_graphics 'SHELXTL-Plus (Sheldrick, 1990)' _computing_publication_material 'SHELXL93 (Sheldrick, 1993)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'P4 diffractometer' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 779 _diffrn_reflns_theta_max 56.74 _diffrn_reflns_theta_min 2.00 _diffrn_standards_decay_% 2 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 4.385 _exptl_absorpt_correction_T_max 0.496 _exptl_absorpt_correction_T_min 0.067 _exptl_absorpt_correction_type 'semi-empirical via \y scan' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.539 _exptl_crystal_description rectangular _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.175 _refine_diff_density_min -0.131 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.231 _refine_ls_goodness_of_fit_obs 1.259 _refine_ls_hydrogen_treatment 'All H atoms are refined isotropically' _refine_ls_matrix_type full _refine_ls_number_parameters 111 _refine_ls_number_reflns 776 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.375 _refine_ls_restrained_S_obs 1.259 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_obs 0.0482 _refine_ls_shift/esd_max -0.004 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ; calc w = 1/[\s^2^(F~o~^2^) + (0.0732P)^2^ + 0.4705P] where P = (F~o~^2^ + 2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.1736 _refine_ls_wR_factor_obs 0.1515 _reflns_number_observed 717 _reflns_number_total 779 _reflns_observed_criterion >2sigma(I) _cod_data_source_file sz1041.cif _cod_data_source_block I _cod_original_formula_sum 'C7 H5 Cl1 N2' _cod_database_code 2005184 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x+1/2, y, -z+1/2' 'x, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0970(10) 0.0840(10) 0.0980(10) 0.0010(10) 0.0000(10) 0.0200(10) C1 0.077(2) 0.070(2) 0.068(2) 0.001(2) 0.000(2) -0.006(2) C2 0.086(3) 0.085(3) 0.074(2) -0.002(2) 0.003(2) -0.002(2) C3 0.092(3) 0.081(2) 0.074(2) -0.007(2) 0.006(2) -0.002(2) C4 0.110(3) 0.081(2) 0.068(2) 0.004(2) -0.005(2) 0.000(2) C5 0.090(3) 0.085(3) 0.072(2) 0.002(2) -0.004(2) 0.000(2) C6 0.075(2) 0.073(2) 0.071(2) -0.002(2) 0.001(2) -0.008(2) N7 0.089(2) 0.073(2) 0.077(2) -0.0010(10) -0.0010(10) -0.0010(10) C8 0.083(2) 0.068(2) 0.075(2) 0.003(2) -0.001(2) -0.003(2) N9 0.071(2) 0.076(2) 0.078(2) 0.0000(10) 0.0040(10) 0.0010(10) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_type_symbol Cl1 1 0.4035(1) 0.8919(1) 0.4074(1) 0.0932(6) Uani d Cl C1 1 0.3336(4) 0.5947(4) 0.5855(2) 0.0717(10) Uani d C C2 1 0.2630(5) 0.4948(4) 0.6377(3) 0.0816(11) Uani d C C3 1 0.3337(4) 0.4102(4) 0.6985(2) 0.0824(11) Uani d C C4 1 0.4731(5) 0.4262(4) 0.7083(2) 0.0862(11) Uani d C C5 1 0.5434(4) 0.5276(4) 0.6574(2) 0.0820(11) Uani d C C6 1 0.4715(4) 0.6126(4) 0.5948(2) 0.0731(10) Uani d C N7 1 0.5175(3) 0.7213(3) 0.5343(2) 0.0797(9) Uani d N C8 1 0.4081(3) 0.7607(4) 0.4920(3) 0.0752(10) Uani d C N9 1 0.2945(3) 0.6925(3) 0.5173(2) 0.0748(9) Uani d N H2 1 0.1816(44) 0.4819(50) 0.6268(30) 0.092(14) Uiso d H H3 1 0.2735(39) 0.3418(40) 0.7352(26) 0.085(10) Uiso d H H4 1 0.5254(34) 0.3690(34) 0.7493(23) 0.064(9) Uiso d H H5 1 0.6409(46) 0.5455(48) 0.6626(28) 0.095(12) Uiso d H H9 1 0.2058(56) 0.7167(60) 0.5071(35) 0.125(16) Uiso d H 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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_publ_flag C2 C1 C6 122.0(3) yes C2 C1 N9 132.5(4) yes C6 C1 N9 105.6(3) yes C3 C2 C1 117.9(4) yes C3 C2 H2 123.(3) no C1 C2 H2 119.(3) no C2 C3 C4 120.9(4) yes C2 C3 H3 113.(2) no C4 C3 H3 127.(2) no C5 C4 C3 121.3(4) yes C5 C4 H4 116.(2) no C3 C4 H4 123.(2) no C4 C5 C6 117.7(4) yes C4 C5 H5 125.(3) no C6 C5 H5 117.(3) no C1 C6 C5 120.2(3) yes C1 C6 N7 110.3(3) yes C5 C6 N7 129.5(4) yes C8 N7 C6 102.6(3) yes N7 C8 N9 116.5(3) yes N7 C8 Cl1 123.5(3) yes N9 C8 Cl1 120.0(3) yes C8 N9 C1 105.0(3) yes C8 N9 H9 131.(3) no C1 N9 H9 123.(3) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C8 1.715(4) yes C1 C2 1.379(5) yes C1 C6 1.386(6) yes C1 N9 1.388(5) yes C2 C3 1.366(6) yes C2 H2 0.83(4) no C3 C4 1.400(7) yes C3 H3 1.02(4) no C4 C5 1.376(5) yes C4 H4 0.95(3) no C5 C6 1.392(5) yes C5 H5 0.98(5) no C6 N7 1.403(4) yes N7 C8 1.298(4) yes C8 N9 1.342(5) yes N9 H9 0.92(6) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 70932 2 PubChem 78572