#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2011773.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_2011773 loop_ _publ_author_name 'Jian, Fangfang' 'Bei, Fengli' 'Yang, Xujie' 'Lu, Lude' 'Wang, Xin' 'Razak, Ibrahim Abdul' 'Shanmuga Sundara Raj, S.' 'Fun, Hoong-Kun' _publ_section_title ; 4-(1H-Benzimidazol-3-ium-2-yl)benzoate dihydrate ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 176 _journal_page_last 177 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C14 H10 N2 O2 , 2H2 O' _chemical_formula_sum 'C14 H14 N2 O4' _chemical_formula_weight 274.27 _chemical_name_systematic ; 4-[1H-Benzimidazolium]-Benzene Carbonic Acid dihydrate solvate ; _space_group_IT_number 9 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C 1 c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 96.234(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.5541(2) _cell_length_b 16.3140(8) _cell_length_c 17.5245(9) _cell_measurement_reflns_used 2836 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.36 _cell_measurement_theta_min 2.34 _cell_volume 1294.29(11) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 1990) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full .998 _diffrn_measured_fraction_theta_max .998 _diffrn_measurement_device_type ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .058 _diffrn_reflns_av_sigmaI/netI .061 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 4352 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.34 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu .105 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular slab' _exptl_crystal_F_000 576 _exptl_crystal_size_max .48 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .08 _refine_diff_density_max .18 _refine_diff_density_min -.25 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .97 _refine_ls_hydrogen_treatment 'see text' _refine_ls_matrix_type full _refine_ls_number_parameters 205 _refine_ls_number_reflns 1474 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all .97 _refine_ls_R_factor_all .060 _refine_ls_R_factor_gt .045 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .00 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0593P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .111 _reflns_number_gt 1150 _reflns_number_total 1474 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1423.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M Cc _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2011773 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -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_type_symbol N2 .5276(5) .26258(17) .14519(15) .0335(6) Uani d . 1 N O1 1.4317(6) .49797(19) -.07722(16) .0544(7) Uani d . 1 O O2 1.4672(6) .59464(18) .01262(17) .0554(7) Uani d . 1 O O1W .9502(6) .69114(18) .00665(16) .0517(7) Uani d D 1 O O2W 1.8698(7) .5413(2) -.15967(16) .0593(8) Uani d D 1 O N1 .6511(5) .34087(18) .24503(15) .0350(6) Uani d . 1 N C1 .3826(6) .2317(2) .20484(18) .0351(7) Uani d . 1 C C2 .1938(8) .1653(2) .2078(2) .0457(8) Uani d . 1 C H2A .1420 .1320 .1653 .055 Uiso calc R 1 H C3 .0862(8) .1516(3) .2783(2) .0525(10) Uani d . 1 C H3A -.0405 .1077 .2833 .063 Uiso calc R 1 H C4 .1644(8) .2021(3) .3412(2) .0546(10) Uani d . 1 C H4A .0875 .1906 .3871 .065 Uiso calc R 1 H C5 .3507(8) .2683(3) .3385(2) .0475(9) Uani d . 1 C H5A .4005 .3019 .3808 .057 Uiso calc R 1 H C6 .4598(7) .2815(2) .26800(18) .0380(8) Uani d . 1 C C7 .6851(6) .3278(2) .17099(18) .0313(7) Uani d . 1 C C8 .8679(6) .3777(2) .12518(16) .0310(6) Uani d . 1 C C9 .9271(8) .3509(2) .05292(19) .0417(8) Uani d . 1 C H9A .8532 .3009 .0340 .050 Uiso calc R 1 H C10 1.0959(8) .3988(2) .00925(19) .0412(8) Uani d . 1 C H10A 1.1345 .3805 -.0389 .049 Uiso calc R 1 H C11 1.2077(6) .4733(2) .03591(19) .0341(7) Uani d . 1 C C12 1.1456(8) .4997(2) .10781(19) .0433(8) Uani d . 1 C H12A 1.2178 .5501 .1263 .052 Uiso calc R 1 H C13 .9798(8) .4529(2) .15210(19) .0426(8) Uani d . 1 C H13A .9420 .4716 .2002 .051 Uiso calc R 1 H C14 1.3868(7) .5255(2) -.0130(2) .0392(8) Uani d . 1 C H1N2 .503(10) .237(3) .093(3) .066(13) Uiso d . 1 H H1N1 .730(12) .386(3) .279(3) .086(18) Uiso d . 1 H H1W1 1.105(14) .656(4) .005(5) .15(3) Uiso d D 1 H H2W1 .804(8) .656(2) .007(2) .052(12) Uiso d D 1 H H1W2 2.032(11) .519(4) -.145(4) .12(3) Uiso d D 1 H H2W2 1.739(10) .527(3) -.128(3) .078(16) Uiso d D 1 H 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 N2 .0338(13) .0357(14) .0317(14) -.0038(11) .0076(11) .0013(12) O1 .0501(16) .0737(19) .0422(13) -.0125(13) .0175(11) .0041(13) O2 .0510(15) .0530(16) .0648(16) -.0167(13) .0182(12) .0037(14) O1W .0574(17) .0459(15) .0543(16) -.0161(14) .0175(13) -.0129(13) O2W .0465(15) .083(2) .0486(15) .0035(15) .0082(12) .0269(15) N1 .0333(13) .0449(16) .0269(12) -.0057(13) .0040(10) .0021(12) C1 .0300(14) .0427(18) .0336(16) .0013(13) .0078(12) .0079(14) C2 .0441(18) .0426(19) .050(2) -.0046(16) .0052(15) .0030(17) C3 .0433(19) .055(2) .061(2) -.0054(18) .0122(16) .017(2) C4 .045(2) .078(3) .042(2) -.001(2) .0117(15) .018(2) C5 .0458(18) .069(3) .0286(17) -.0008(18) .0080(13) .0059(17) C6 .0287(15) .052(2) .0331(16) -.0002(15) .0013(12) .0045(14) C7 .0260(13) .0342(16) .0333(16) -.0007(13) .0014(11) .0017(13) C8 .0270(14) .0369(17) .0294(15) -.0007(13) .0044(11) .0048(13) C9 .0452(18) .042(2) .0386(19) -.0123(16) .0093(14) -.0030(16) C10 .0436(17) .049(2) .0324(17) -.0075(17) .0126(13) -.0033(16) C11 .0238(13) .0407(18) .0378(16) -.0013(13) .0027(11) .0042(14) C12 .049(2) .0437(19) .0378(18) -.0157(16) .0071(14) -.0036(15) C13 .0487(19) .047(2) .0333(17) -.0142(17) .0106(14) -.0063(16) C14 .0293(16) .047(2) .0414(18) -.0056(15) .0044(13) .0088(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0000 '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 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0000 '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 C7 N2 C1 108.4(3) C7 N2 H1N2 130(3) C1 N2 H1N2 121(3) H1W1 O1W H2W1 101(6) H1W2 O2W H2W2 109(6) C7 N1 C6 108.1(3) C7 N1 H1N1 129(3) C6 N1 H1N1 123(3) C2 C1 C6 122.2(3) C2 C1 N2 131.1(3) C6 C1 N2 106.7(3) C1 C2 C3 115.9(4) C1 C2 H2A 122.1 C3 C2 H2A 122.1 C4 C3 C2 121.5(4) C4 C3 H3A 119.3 C2 C3 H3A 119.3 C5 C4 C3 122.9(3) C5 C4 H4A 118.5 C3 C4 H4A 118.5 C4 C5 C6 115.5(4) C4 C5 H5A 122.2 C6 C5 H5A 122.2 C1 C6 N1 106.8(3) C1 C6 C5 122.1(3) N1 C6 C5 131.1(3) N2 C7 N1 109.9(3) N2 C7 C8 125.0(3) N1 C7 C8 125.0(3) C13 C8 C9 119.0(3) C13 C8 C7 120.9(3) C9 C8 C7 120.1(3) C10 C9 C8 120.0(3) C10 C9 H9A 120.0 C8 C9 H9A 120.0 C11 C10 C9 121.1(3) C11 C10 H10A 119.4 C9 C10 H10A 119.4 C10 C11 C12 118.4(3) C10 C11 C14 120.5(3) C12 C11 C14 121.0(3) C13 C12 C11 121.3(3) C13 C12 H12A 119.4 C11 C12 H12A 119.4 C12 C13 C8 120.2(3) C12 C13 H13A 119.9 C8 C13 H13A 119.9 O1 C14 O2 125.2(3) O1 C14 C11 117.4(3) O2 C14 C11 117.3(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N2 C7 1.334(4) yes N2 C1 1.390(4) yes N2 H1N2 .99(5) ? O1 C14 1.249(4) yes O2 C14 1.254(5) yes O1W H1W1 .91(4) ? O1W H2W1 .88(3) ? O2W H1W2 .84(4) ? O2W H2W2 .89(3) ? N1 C7 1.340(4) yes N1 C6 1.391(4) yes N1 H1N1 .98(6) ? C1 C2 1.387(5) ? C1 C6 1.387(5) ? C2 C3 1.396(5) ? C2 H2A .9300 ? C3 C4 1.391(6) ? C3 H3A .9300 ? C4 C5 1.377(6) ? C4 H4A .9300 ? C5 C6 1.398(4) ? C5 H5A .9300 ? C7 C8 1.465(4) ? C8 C13 1.392(5) ? C8 C9 1.393(4) ? C9 C10 1.384(5) ? C9 H9A .9300 ? C10 C11 1.379(5) ? C10 H10A .9300 ? C11 C12 1.390(5) ? C11 C14 1.510(4) ? C12 C13 1.372(5) ? C12 H12A .9300 ? C13 H13A .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 _geom_hbond_publ_flag O1W H1W1 O2 1_555 .91(6) 1.92(6) 2.825(4) 171(7) yes O1W H2W1 O2 1_455 .88(4) 1.84(4) 2.716(4) 172(3) yes O2W H2W2 O1 1_555 .89(5) 1.80(5) 2.682(4) 171(5) yes O2W H1W2 O1 1_655 .84(6) 2.09(6) 2.887(4) 158(6) yes N1 H1N1 O2W 2_465 .99(5) 1.68(5) 2.667(4) 177(5) yes N2 H1N2 O1W 3_445 1.00(5) 1.68(5) 2.682(4) 177(4) yes C9 H9A O1W 3_445 .9297 2.5716 3.433(4) 154 yes C13 H13A O2W 2_465 .9299 2.5216 3.391(4) 156 yes 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 C7 N2 C1 C2 -180.0(4) C7 N2 C1 C6 .1(3) C6 C1 C2 C3 -.1(5) N2 C1 C2 C3 180.0(3) C1 C2 C3 C4 .3(6) C2 C3 C4 C5 .0(6) C3 C4 C5 C6 -.5(6) C2 C1 C6 N1 179.6(3) N2 C1 C6 N1 -.4(3) C2 C1 C6 C5 -.4(5) N2 C1 C6 C5 179.6(3) C7 N1 C6 C1 .6(4) C7 N1 C6 C5 -179.4(3) C4 C5 C6 C1 .7(5) C4 C5 C6 N1 -179.4(4) C1 N2 C7 N1 .3(3) C1 N2 C7 C8 -179.7(3) C6 N1 C7 N2 -.6(3) C6 N1 C7 C8 179.4(3) N2 C7 C8 C13 167.9(3) N1 C7 C8 C13 -12.1(5) N2 C7 C8 C9 -10.8(5) N1 C7 C8 C9 169.2(3) C13 C8 C9 C10 .3(5) C7 C8 C9 C10 178.9(3) C8 C9 C10 C11 .0(5) C9 C10 C11 C12 -.4(5) C9 C10 C11 C14 -178.9(3) C10 C11 C12 C13 .7(5) C14 C11 C12 C13 179.1(3) C11 C12 C13 C8 -.5(6) C9 C8 C13 C12 .0(5) C7 C8 C13 C12 -178.6(3) C10 C11 C14 O1 -1.1(4) C12 C11 C14 O1 -179.5(3) C10 C11 C14 O2 175.9(3) C12 C11 C14 O2 -2.5(5)