#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/22/2012220.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_2012220 loop_ _publ_author_name 'Hashizume, Daisuke' 'Iegaki, Masataka' 'Yasui, Masanori' 'Iwasaki, Fujiko' 'Meng, Jiben' 'Wen, Zhong' 'Matsuura, Teruo' _publ_section_title ; Two-component molecular crystals from N-heteroaromatics and nitrobenzoic acids ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1067 _journal_page_last 1072 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C7 H7 N2 + , C7 H4 N O4 -' _chemical_formula_sum 'C14 H11 N3 O4' _chemical_formula_weight 285.26 _chemical_melting_point 436.0(10) _chemical_name_systematic ; Benzimidazolium 4-nitrobenzoate ; _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' _cell_angle_alpha 90 _cell_angle_beta 94.1400(17) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.8524(5) _cell_length_b 7.6666(4) _cell_length_c 12.5193(7) _cell_measurement_reflns_used 22373 _cell_measurement_temperature 297 _cell_measurement_theta_max 30.03 _cell_measurement_theta_min 2.95 _cell_volume 1326.09(11) _computing_cell_refinement PROCESS-AUTO _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1993)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 297 _diffrn_detector_area_resol_mean 10 _diffrn_measured_fraction_theta_full .998 _diffrn_measured_fraction_theta_max .998 _diffrn_measurement_device_type 'Rigaku R-AXIS Rapid' _diffrn_measurement_method oscillation _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 .034 _diffrn_reflns_av_sigmaI/netI .029 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 23459 _diffrn_reflns_theta_full 30.03 _diffrn_reflns_theta_max 30.03 _diffrn_reflns_theta_min 2.95 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count none _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .108 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 592 _exptl_crystal_size_max .60 _exptl_crystal_size_mid .38 _exptl_crystal_size_min .33 _refine_diff_density_max .22 _refine_diff_density_min -.19 _refine_ls_extinction_coef .017(3) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 3869 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.073 _refine_ls_R_factor_all .075 _refine_ls_R_factor_gt .053 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0675P)^2^+0.2721P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .153 _reflns_number_gt 2856 _reflns_number_total 3869 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ob1039.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '435-437' was changed to '436.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '435-437' was changed to '436.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012220 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 O1A .27374(8) .28350(18) .35534(9) .0571(3) Uani d . 1 . . O O2A .34931(7) .09537(17) .46916(9) .0516(3) Uani d . 1 . . O O3A -.12902(9) .2382(3) .64492(13) .0831(5) Uani d . 1 . . O O4A -.05470(11) .0597(3) .75529(13) .0930(6) Uani d . 1 . . O N1A -.05868(10) .1511(2) .67521(12) .0584(4) Uani d . 1 . . N C1A .18762(9) .17376(19) .49722(11) .0380(3) Uani d . 1 . . C C2A .10543(10) .2684(2) .46465(13) .0475(4) Uani d . 1 . . C H2A .1051 .3376 .4036 .057 Uiso calc R 1 . . H C3A .02391(10) .2609(2) .52211(14) .0501(4) Uani d . 1 . . C H3A -.0316 .3234 .5003 .060 Uiso calc R 1 . . H C4A .02729(10) .1582(2) .61241(12) .0439(3) Uani d . 1 . . C C5A .10692(11) .0611(2) .64667(13) .0522(4) Uani d . 1 . . C H5A .1067 -.0077 .7078 .063 Uiso calc R 1 . . H C6A .18778(11) .0686(2) .58728(13) .0487(4) Uani d . 1 . . C H6A .2423 .0027 .6081 .058 Uiso calc R 1 . . H C7A .27719(9) .1857(2) .43537(11) .0421(3) Uani d . 1 . . C N1B .55467(9) .46429(19) .18892(10) .0463(3) Uani d . 1 . . N H1B .5815 .5001 .1331 .056 Uiso calc R 1 . . H C2B .46107(11) .4322(2) .19447(12) .0458(4) Uani d . 1 . . C H2B .4142 .4451 .1380 .055 Uiso calc R 1 . . H N3B .44405(9) .37930(19) .29193(10) .0456(3) Uani d . 1 . . N H3B .3884 .3521 .3133 .055 Uiso calc R 1 . . H C4B .55510(13) .3278(2) .46050(13) .0520(4) Uani d . 1 . . C H4B .5081 .2906 .5048 .062 Uiso calc R 1 . . H C5B .65128(14) .3387(3) .49696(15) .0597(5) Uani d . 1 . . C H5B .6695 .3076 .5673 .072 Uiso calc R 1 . . H C6B .72176(13) .3953(3) .43094(17) .0633(5) Uani d . 1 . . C H6B .7858 .4016 .4586 .076 Uiso calc R 1 . . H C7B .69926(11) .4423(3) .32573(16) .0567(4) Uani d . 1 . . C H7B .7465 .4800 .2820 .068 Uiso calc R 1 . . H C7aB .60221(10) .4304(2) .28809(12) .0415(3) Uani d . 1 . . C C3aB .53164(10) .3751(2) .35423(12) .0403(3) 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 O1A .0380(5) .0857(9) .0490(6) -.0013(6) .0140(5) .0177(6) O2A .0357(5) .0772(8) .0437(6) .0115(5) .0143(4) .0013(5) O3A .0408(6) .1263(14) .0853(10) .0152(8) .0258(6) .0015(10) O4A .0616(9) .1499(17) .0720(9) .0005(10) .0359(7) .0297(10) N1A .0376(6) .0861(11) .0536(8) -.0065(7) .0184(6) -.0085(8) C1A .0305(6) .0470(7) .0376(7) -.0014(5) .0096(5) -.0027(6) C2A .0359(6) .0595(9) .0483(8) .0037(6) .0108(6) .0112(7) C3A .0328(6) .0601(10) .0587(9) .0072(6) .0120(6) .0033(8) C4A .0327(6) .0570(9) .0439(7) -.0055(6) .0152(5) -.0079(6) C5A .0417(7) .0708(11) .0457(8) -.0007(7) .0150(6) .0120(8) C6A .0354(7) .0628(10) .0494(8) .0059(7) .0122(6) .0098(7) C7A .0310(6) .0600(9) .0362(7) -.0019(6) .0096(5) -.0029(6) N1B .0394(6) .0614(8) .0397(6) -.0060(6) .0133(5) .0019(6) C2B .0384(7) .0606(9) .0390(7) -.0055(7) .0064(6) .0027(7) N3B .0340(5) .0623(8) .0416(6) -.0039(5) .0103(5) .0065(6) C4B .0537(9) .0589(9) .0437(8) -.0027(7) .0065(7) .0065(7) C5B .0623(10) .0610(10) .0536(10) -.0002(8) -.0101(8) .0062(8) C6B .0434(8) .0647(11) .0793(13) -.0034(8) -.0115(8) .0051(10) C7B .0358(7) .0650(10) .0698(11) -.0060(7) .0069(7) .0026(9) C7aB .0367(6) .0448(7) .0438(7) -.0009(6) .0096(6) -.0015(6) C3aB .0360(6) .0450(7) .0406(7) -.0014(5) .0072(5) .0000(6) 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 O1A C7A . 1.2494(19) yes O2A C7A . 1.2632(18) yes O3A N1A . 1.219(2) ? O4A N1A . 1.221(2) ? N1A C4A . 1.4746(17) ? C1A C6A . 1.386(2) ? C1A C2A . 1.386(2) ? C1A C7A . 1.5120(17) ? C2A C3A . 1.383(2) ? C2A H2A . .9300 ? C3A C4A . 1.376(2) ? C3A H3A . .9300 ? C4A C5A . 1.374(2) ? C5A C6A . 1.3896(19) ? C5A H5A . .9300 ? C6A H6A . .9300 ? N1B C2B . 1.3265(18) yes N1B C7aB . 1.387(2) ? N1B H1B . .8600 ? N3B C2B . 1.3231(19) yes C2B H2B . .9300 ? N3B C3aB . 1.3947(19) ? N3B H3B . .8600 ? C4B C5B . 1.379(2) ? C4B C3aB . 1.395(2) ? C4B H4B . .9300 ? C5B C6B . 1.393(3) ? C5B H5B . .9300 ? C6B C7B . 1.379(3) ? C6B H6B . .9300 ? C7B C7aB . 1.395(2) ? C7B H7B . .9300 ? C7aB C3aB . 1.3922(19) ? 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O3A N1A O4A 123.88(14) O3A N1A C4A 118.16(16) O4A N1A C4A 117.95(15) C6A C1A C2A 119.79(12) C6A C1A C7A 119.91(13) C2A C1A C7A 120.30(13) C3A C2A C1A 120.61(14) C3A C2A H2A 119.7 C1A C2A H2A 119.7 C4A C3A C2A 118.08(14) C4A C3A H3A 121.0 C2A C3A H3A 121.0 C5A C4A C3A 123.07(13) C5A C4A N1A 118.34(14) C3A C4A N1A 118.59(14) C4A C5A C6A 118.08(15) C4A C5A H5A 121.0 C6A C5A H5A 121.0 C1A C6A C5A 120.36(14) C1A C6A H6A 119.8 C5A C6A H6A 119.8 O1A C7A O2A 125.53(12) O1A C7A C1A 117.49(13) O2A C7A C1A 116.98(13) C2B N1B C7aB 108.73(12) C2B N1B H1B 125.6 C7aB N1B H1B 125.6 N3B C2B N1B 110.19(14) N3B C2B H2B 124.9 N1B C2B H2B 124.9 C2B N3B C3aB 108.49(12) C2B N3B H3B 125.8 C3aB N3B H3B 125.8 C5B C4B C3aB 116.93(15) C5B C4B H4B 121.5 C3aB C4B H4B 121.5 C4B C5B C6B 121.61(17) C4B C5B H5B 119.2 C6B C5B H5B 119.2 C7B C6B C5B 121.88(16) C7B C6B H6B 119.1 C5B C6B H6B 119.1 C6B C7B C7aB 116.84(15) C6B C7B H7B 121.6 C7aB C7B H7B 121.6 N1B C7aB C3aB 106.32(12) N1B C7aB C7B 132.36(14) C3aB C7aB C7B 121.32(15) C7aB C3aB C4B 121.43(14) C7aB C3aB N3B 106.27(12) C4B C3aB N3B 132.30(13) 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 N1B H1B O2A 2_655 .86 1.81 2.6600(15) 171 N3B H3B O1A . .86 1.79 2.6469(15) 177 C2B H2B O2A 4_565 .93 2.26 3.125(2) 155 C6B H6B O3A 1_655 .93 2.83 3.478(3) 128 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 C6A C1A C2A C3A .9(3) C7A C1A C2A C3A -178.65(15) C1A C2A C3A C4A .5(3) C2A C3A C4A C5A -1.2(3) C2A C3A C4A N1A 179.15(15) O3A N1A C4A C5A 179.58(17) O4A N1A C4A C5A .5(3) O3A N1A C4A C3A -.7(2) O4A N1A C4A C3A -179.87(18) C3A C4A C5A C6A .5(3) N1A C4A C5A C6A -179.88(16) C2A C1A C6A C5A -1.7(3) C7A C1A C6A C5A 177.90(15) C4A C5A C6A C1A 1.0(3) C6A C1A C7A O1A -179.36(15) C2A C1A C7A O1A .2(2) C6A C1A C7A O2A .8(2) C2A C1A C7A O2A -179.65(15) C7aB N1B C2B N3B .10(19) N1B C2B N3B C3aB -.39(19) C3aB C4B C5B C6B .4(3) C4B C5B C6B C7B -.4(3) C5B C6B C7B C7aB .0(3) C2B N1B C7aB C3aB .22(17) C2B N1B C7aB C7B 179.98(18) C6B C7B C7aB N1B -179.22(17) C6B C7B C7aB C3aB .5(3) N1B C7aB C3aB C4B 179.24(15) C7B C7aB C3aB C4B -.5(2) N1B C7aB C3aB N3B -.44(17) C7B C7aB C3aB N3B 179.77(15) C5B C4B C3aB C7aB .1(3) C5B C4B C3aB N3B 179.69(17) C2B N3B C3aB C7aB .51(18) C2B N3B C3aB C4B -179.12(18)