#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/04/2200441.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_2200441 loop_ _publ_author_name 'Pifferi, Augusto' 'Camalli, Mercedes' 'Silvestri, Romano' 'De Martino, Gabriella' 'Massa, Silvio' 'Artico, Marino' _publ_section_title ; 1-Amino-6-chloro-2-(1H-pyrrol-2-yl)benzimidazole (RS 1350) ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o819 _journal_page_last o821 _journal_paper_doi 10.1107/S1600536801010856 _journal_volume 57 _journal_year 2001 _chemical_formula_sum 'C11 H9 Cl N4' _chemical_formula_weight 232.67 _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' _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_formula_units_Z 8 _cell_length_a 10.065(2) _cell_length_b 23.178(4) _cell_length_c 9.077(3) _cell_measurement_reflns_used 32 _cell_measurement_temperature 293 _cell_measurement_theta_max 16.02 _cell_measurement_theta_min 2.85 _cell_volume 2117.5(9) _computing_cell_refinement R3m/V _computing_data_collection 'R3m/V (Siemens, 1989)' _computing_data_reduction 'XDISK (Siemens, 1989) ' _computing_molecular_graphics CAOS _computing_publication_material CAOS _computing_structure_refinement 'CAOS (Camalli & Spagna, 1994)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 293 _diffrn_measured_fraction_theta_full .99 _diffrn_measured_fraction_theta_max .99 _diffrn_measurement_device 'Siemens P3 automatic four circle' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .063 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 5213 _diffrn_reflns_theta_full 35.07 _diffrn_reflns_theta_max 35.07 _diffrn_reflns_theta_min 1.76 _diffrn_standards_decay_% none _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .336 _exptl_absorpt_correction_type none _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 960 _exptl_crystal_size_max .3 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .15 _refine_diff_density_max .26 _refine_diff_density_min -.24 _refine_ls_abs_structure_details ; ; _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all .970 _refine_ls_goodness_of_fit_ref .970 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 1194 _refine_ls_R_factor_all .042 _refine_ls_R_factor_gt .042 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef F _refine_ls_weighting_details ' w=1/(0.2+F+0.0792F^2^)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .070 _refine_ls_wR_factor_ref .070 _reflns_number_gt 1194 _reflns_number_total 4669 _reflns_threshold_expression F>3\s(F) _cod_data_source_file ci6034.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_atom_site_thermal_displace_type' value 'uani' changed to 'Uani' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (16 times). '_atom_site_thermal_displace_type' value 'uiso' changed to 'Uiso' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_refine_ls_matrix_type' value 'Full' changed to 'full' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_atom_site_thermal_displace_type' value 'uani' changed to 'Uani' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (16 times). '_atom_site_thermal_displace_type' value 'uiso' changed to 'Uiso' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2200441 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,-y,-z 1/2-x,-y,1/2+z 1/2+x,+y,1/2-z 1/2+x,1/2-y,-z 1/2-x,1/2+y,+z -x,1/2+y,1/2-z +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 .0788(9) .0509(6) .0812(9) -.0224(6) -.0011(7) -.0001(6) N1 .0320(10) .041(2) .036(2) .0040(10) .0040(10) -.0010(10) N2 .041(2) .057(2) .036(2) .001(2) .0090(10) -.002(2) N3 .038(2) .042(2) .041(2) .0000(10) .004(2) .0000(10) N4 .047(2) .051(2) .047(2) .004(2) .005(2) -.005(2) C1 .032(2) .038(2) .036(2) .0000(10) -.003(2) .003(2) C2 .034(2) .040(2) .034(2) .0030(10) .000(2) .003(2) C3 .035(2) .042(2) .038(2) .002(2) .001(2) .001(2) C4 .037(2) .050(2) .043(2) -.002(2) -.001(2) .005(2) C5 .045(2) .041(2) .056(2) -.008(2) -.011(2) .002(2) C6 .054(3) .042(2) .049(2) -.001(2) -.008(2) -.004(2) C7 .042(2) .051(2) .040(2) .005(2) -.002(2) -.006(2) C8 .041(2) .037(2) .039(2) .0040(10) -.004(2) -.001(2) C9 .048(2) .041(2) .049(2) -.003(2) .000(2) .003(2) C10 .058(3) .038(2) .062(3) -.003(2) -.013(2) .005(2) C11 .064(3) .044(2) .058(3) .006(2) -.005(2) -.007(2) loop_ _atom_site_label _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_occupancy Cl1 .84840(10) .27550(10) .2733(2) .0703(5) Uani 1.000 N1 .6985(3) .06430(10) .1606(3) .0360(10) Uani 1.000 N2 .7708(3) .0462(2) .0358(3) .0450(10) Uani 1.000 N3 .5533(3) .05910(10) .3468(4) .0410(10) Uani 1.000 N4 .6142(4) -.0547(2) .0682(4) .0480(10) Uani 1.000 C1 .6053(4) .0316(2) .2325(4) .0360(10) Uani 1.000 C2 .7060(4) .1169(2) .2311(4) .0360(10) Uani 1.000 C3 .6153(4) .1128(2) .3482(4) .0390(10) Uani 1.000 C4 .7788(4) .1668(2) .2034(4) .0440(10) Uani 1.000 C5 .7592(4) .2115(2) .3006(5) .0470(10) Uani 1.000 C6 .6718(4) .2087(2) .4191(5) .0480(10) Uani 1.000 C7 .5993(4) .1592(2) .4451(4) .0440(10) Uani 1.000 C8 .5653(4) -.0262(2) .1893(4) .0390(10) Uani 1.000 C9 .4711(4) -.0606(2) .2537(5) .0460(10) Uani 1.000 C10 .4638(5) -.1115(2) .1688(5) .0530(10) Uani 1.000 C11 .5529(5) -.1064(2) .0557(5) .055(2) Uani 1.000 H1a .8641 .0477 .0574 .046 Uiso 1.000 H1b .7514 .0716 -.0449 .046 Uiso 1.000 H4n .6815 -.0402 .0030 .048 Uiso 1.000 H4c .8387 .1699 .1216 .044 Uiso 1.000 H6 .6620 .2414 .4831 .048 Uiso 1.000 H7 .5394 .1566 .5271 .045 Uiso 1.000 H9 .4200 -.0517 .3401 .047 Uiso 1.000 H10 .4067 -.1438 .1875 .052 Uiso 1.000 H11 .5681 -.1346 -.0199 .057 Uiso 1.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'H ' 'Hydrogen ' .0000 .0000 ' Int. Tab. C, 4.2.6.8, 6.1.1.4' 'C ' 'Carbon ' .0020 .0020 ' Int. Tab. C, 4.2.6.8, 6.1.1.4' 'N ' 'Nitrogen ' .0040 .0030 ' Int. Tab. C, 4.2.6.8, 6.1.1.4' 'Cl ' 'Chlorine ' .1320 .1590 ' Int. Tab. C, 4.2.6.8, 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 2 3 3 4 4 -4 0 0 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 N2 N1 C1 124.8(3) no C2 N1 C1 107.8(3) no C2 N1 N2 127.4(3) no H1a N2 H1b 109.5 no N1 N2 H1b 109.0 no N1 N2 H1a 109.3 no C1 N3 C3 105.1(3) no H4n N4 C11 125.4 no C8 N4 C11 109.2(4) no C8 N4 H4n 125.3 no N1 C1 C8 124.8(3) no N3 C1 C8 123.1(3) no N3 C1 N1 112.1(3) no N1 C2 C3 104.7(3) no C4 C2 C3 122.4(3) no C4 C2 N1 132.8(3) no C2 C3 N3 110.2(3) no C7 C3 N3 129.9(3) no C7 C3 C2 119.8(4) no H4c C4 C2 122.3 no C5 C4 C2 115.8(4) no C5 C4 H4c 121.9 no Cl1 C5 C6 118.2(3) no C4 C5 C6 123.5(4) no C4 C5 Cl1 118.3(3) no H6 C6 C5 119.7 no C7 C6 C5 120.3(4) no C7 C6 H6 119.9 no H7 C7 C3 120.7 no C6 C7 C3 118.1(4) no C6 C7 H7 121.1 no C1 C8 N4 124.1(3) no C9 C8 N4 108.1(3) no C9 C8 C1 127.8(4) no C10 C9 H9 126.7 no C8 C9 H9 126.5 no C8 C9 C10 106.8(4) no H10 C10 C9 126.0 no C11 C10 C9 107.8(4) no C11 C10 H10 126.3 no C10 C11 N4 108.2(4) no H11 C11 N4 126.1 no H11 C11 C10 125.7 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C5 . . 1.751(4) no N1 N2 . . 1.411(4) no N1 C1 . . 1.372(5) no N1 C2 . . 1.380(5) no N2 H1a . . .96 no N2 H1b . . .96 no N3 C1 . . 1.326(5) no N3 C3 . . 1.391(5) no N4 C8 . . 1.374(5) no N4 C11 . . 1.354(6) no N4 H4n . . .96 no C1 C8 . . 1.452(5) no C2 C3 . . 1.405(5) no C2 C4 . . 1.390(5) no C3 C7 . . 1.399(6) no C4 C5 . . 1.376(6) no C4 H4c . . .96 no C5 C6 . . 1.391(6) no C6 C7 . . 1.380(6) no C6 H6 . . .96 no C7 H7 . . .96 no C8 C9 . . 1.370(6) no C9 C10 . . 1.411(6) no C9 H9 . . .96 no C10 C11 . . 1.367(7) no C10 H10 . . .96 no C11 H11 . . .96 no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21132740 2 PubChem 5260189