#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/07/2200700.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_2200700 loop_ _publ_author_name 'Blake, Alexander J.' 'Hill, Stuart J.' 'Hubberstey, Peter' _publ_section_title ; 2-Dihydroxymethyl-3H-benzoimidazol-1-ium chloride monohydrate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1258 _journal_page_last o1260 _journal_paper_doi 10.1107/S1600536801020074 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C8 H9 N2 O2 1+, Cl 1-, H2 O' _chemical_formula_moiety 'C8 H9 N2 O2 1+, Cl 1-, H2 O' _chemical_formula_sum 'C8 H11 Cl N2 O3' _chemical_formula_weight 218.64 _chemical_name_common ; 1H-Benzimidazole-2-methanediol monohydrochloride monohydrate ; _chemical_name_systematic ; 1H-Benzimidazole-2-methanediol monohydrochloride monohydrate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 103.38(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.513(4) _cell_length_b 4.977(3) _cell_length_c 16.388(9) _cell_measurement_reflns_used 22 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 17.4 _cell_measurement_theta_min 13.3 _cell_volume 992.9(9) _computing_cell_refinement STADI4 _computing_data_collection 'STADI4 (Stoe & Cie, 1995)' _computing_data_reduction 'X-RED (Stoe & Cie, 1995)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2001)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full .995 _diffrn_measured_fraction_theta_max .995 _diffrn_measurement_device_type 'Stoe Stadi-4 four-circle' _diffrn_measurement_method \w/\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_sigmaI/netI .019 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1724 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.71 _diffrn_standards_decay_% none _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .368 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description tablet _exptl_crystal_F_000 456 _exptl_crystal_size_max .48 _exptl_crystal_size_mid .29 _exptl_crystal_size_min .19 _refine_diff_density_max .24 _refine_diff_density_min -.21 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.21 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 1724 _refine_ls_number_restraints 7 _refine_ls_restrained_S_all 1.21 _refine_ls_R_factor_all .049 _refine_ls_R_factor_gt .037 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.038P)^2^+0.848P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .100 _reflns_number_gt 1470 _reflns_number_total 1724 _reflns_threshold_expression I>2\s(I) _cod_data_source_file na6106.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2200700 _cod_database_fobs_code 2200700 loop_ _symmetry_equiv_pos_as_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_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 .28249(5) .80898(12) .96645(4) .02668(19) Uani d . 1 . . Cl O1 .25808(15) .3143(4) .84544(11) .0294(4) Uani d D 1 . . O H11 .258(3) .433(4) .8807(14) .044 Uiso d D 1 . . H H12 .258(3) .171(3) .8707(16) .044 Uiso d D 1 . . H N1 .69793(16) .7279(4) .90177(12) .0217(4) Uani d D 1 . . N H1 .690(2) .856(4) .9365(13) .026 Uiso d D 1 . . H C2 .61967(18) .5670(5) .86111(14) .0206(5) Uani d . 1 . . C C21 .50278(18) .5737(5) .87029(15) .0228(5) Uani d . 1 . . C H21 .4951 .4582 .9170 .027 Uiso calc R 1 . . H O211 .48246(14) .8408(4) .88820(12) .0339(5) Uani d D 1 . . O H211 .4298(18) .828(7) .9098(19) .051 Uiso d D 1 . . H O212 .43511(13) .4791(3) .79537(10) .0235(4) Uani d D 1 . . O H212 .3827(16) .405(6) .8075(18) .035 Uiso d D 1 . . H N3 .66070(15) .3899(4) .81622(12) .0207(4) Uani d D 1 . . N H3 .6232(18) .267(4) .7831(14) .025 Uiso d D 1 . . H C4 .77345(18) .4340(5) .82920(14) .0213(5) Uani d . 1 . . C C5 .85463(19) .3080(5) .79801(15) .0264(5) Uani d . 1 . . C H5 .8388 .1666 .7600 .032 Uiso calc R 1 . . H C6 .9600(2) .4041(6) .82642(16) .0310(6) Uani d . 1 . . C H6 1.0169 .3239 .8075 .037 Uiso calc R 1 . . H C7 .9840(2) .6184(6) .88284(17) .0326(6) Uani d . 1 . . C H7 1.0564 .6762 .9004 .039 Uiso calc R 1 . . H C8 .9032(2) .7463(5) .91312(16) .0287(6) Uani d . 1 . . C H8 .9190 .8893 .9505 .034 Uiso calc R 1 . . H C9 .79728(18) .6493(5) .88453(14) .0208(5) Uani d . 1 . . C 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 .0323(3) .0220(3) .0277(3) -.0022(2) .0110(2) -.0041(2) O1 .0351(10) .0228(10) .0319(10) -.0030(8) .0108(8) -.0017(8) N1 .0235(10) .0196(10) .0221(10) .0008(8) .0057(8) -.0031(8) C2 .0229(11) .0195(12) .0188(11) .0017(10) .0033(9) .0030(10) C21 .0219(12) .0233(13) .0235(12) .0020(10) .0057(9) -.0004(10) O211 .0270(9) .0285(10) .0498(12) .0024(8) .0164(8) -.0109(9) O212 .0204(8) .0254(9) .0242(8) -.0030(7) .0042(7) .0020(7) N3 .0190(10) .0199(10) .0219(10) -.0004(8) .0022(8) -.0032(8) C4 .0206(11) .0221(12) .0211(11) .0011(10) .0043(9) .0035(10) C5 .0288(12) .0255(13) .0261(12) .0034(11) .0089(10) .0000(11) C6 .0241(12) .0364(15) .0349(14) .0042(11) .0118(10) .0039(12) C7 .0214(12) .0370(15) .0386(15) -.0051(11) .0053(10) .0029(12) C8 .0272(12) .0274(14) .0299(13) -.0060(11) .0032(10) -.0011(11) C9 .0217(11) .0188(12) .0219(11) .0016(10) .0052(9) .0038(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .1585 '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 C2 N1 C9 108.7(2) N1 C2 N3 110.3(2) N1 C2 C21 124.1(2) N3 C2 C21 125.5(2) O211 C21 O212 113.7(2) O211 C21 C2 105.68(19) O212 C21 C2 108.00(19) C2 N3 C4 108.57(19) C5 C4 C9 121.6(2) C5 C4 N3 132.3(2) C9 C4 N3 106.1(2) C6 C5 C4 116.3(2) C5 C6 C7 122.1(2) C8 C7 C6 121.8(2) C7 C8 C9 116.1(2) C8 C9 C4 122.2(2) C8 C9 N1 131.5(2) C4 C9 N1 106.4(2) H11 O1 H12 105(2) C2 N1 H1 125.9(17) C9 N1 H1 125.3(17) O211 C21 H21 109.8 O212 C21 H21 109.8 C2 C21 H21 109.8 C21 O211 H211 103(3) C21 O212 H212 107(2) C2 N3 H3 125.9(17) C4 N3 H3 125.5(17) C6 C5 H5 121.8 C4 C5 H5 121.8 C5 C6 H6 119.0 C7 C6 H6 119.0 C8 C7 H7 119.1 C6 C7 H7 119.1 C7 C8 H8 121.9 C9 C8 H8 121.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 . 1.320(3) ? N1 C9 . 1.393(3) ? C2 N3 . 1.325(3) ? C2 C21 . 1.505(3) ? C21 O211 . 1.398(3) ? C21 O212 . 1.402(3) ? N3 C4 . 1.395(3) ? C4 C5 . 1.388(3) ? C4 C9 . 1.391(3) ? C5 C6 . 1.378(4) ? C6 C7 . 1.398(4) ? C7 C8 . 1.380(4) ? C8 C9 . 1.387(3) ? O1 H11 . .827(10) ? O1 H12 . .826(10) ? N1 H1 . .876(10) ? C21 H21 . .9800 ? O211 H211 . .819(10) ? O212 H212 . .817(10) ? N3 H3 . .879(10) ? C5 H5 . .9300 ? C6 H6 . .9300 ? C7 H7 . .9300 ? C8 H8 . .9300 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O1 H11 Cl1 . .83(2) 2.32(2) 3.132(2) 169(3) O211 H211 Cl1 . .82(2) 2.25(2) 3.069(2) 178(3) O212 H212 O1 . .82(2) 1.86(2) 2.664(3) 167(3) O1 H12 Cl1 1_545 .83(2) 2.36(2) 3.173(2) 168(3) N1 H1 Cl1 3_677 .88(2) 2.27(2) 3.129(2) 165(2) N3 H3 O212 2_646 .88(2) 1.95(2) 2.819(3) 170(2) 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 C9 N1 C2 N3 -1.5(3) C9 N1 C2 C21 174.3(2) N1 C2 C21 O211 30.8(3) N3 C2 C21 O211 -154.1(2) N1 C2 C21 O212 152.7(2) N3 C2 C21 O212 -32.1(3) N1 C2 N3 C4 1.0(3) C21 C2 N3 C4 -174.7(2) C2 N3 C4 C5 -180.0(2) C2 N3 C4 C9 -.2(2) C9 C4 C5 C6 1.5(3) N3 C4 C5 C6 -178.7(2) C4 C5 C6 C7 -.7(4) C5 C6 C7 C8 -.2(4) C6 C7 C8 C9 .2(4) C7 C8 C9 C4 .6(4) C7 C8 C9 N1 179.8(2) C5 C4 C9 C8 -1.5(4) N3 C4 C9 C8 178.7(2) C5 C4 C9 N1 179.2(2) N3 C4 C9 N1 -.7(2) C2 N1 C9 C8 -177.9(2) C2 N1 C9 C4 1.3(3)