#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/67/2226715.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_2226715
loop_
_publ_author_name
'Shao, Zhi-Dong'
'Jiang, Xiao'
'Lan, Shao-Min'
'Di, Wen-Jing'
'Liang, Yun-Xiao'
_publ_section_title
;
 6-Nitrobenzimidazolium dihydrogen phosphate 6-nitrobenzimidazole
 solvate dihydrate
;
_journal_coeditor_code           WM2359
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1757
_journal_page_last               o1758
_journal_paper_doi               10.1107/S1600536810023603
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'C7 H6 N3 O2 +, H2 P O4 -, C7 H5 N3 O2, 2H2 O'
_chemical_formula_moiety
'C7 H6 N3 O2 +, H2 P O4 -, (C7 H5 N3 O2), 2(H2 O)'
_chemical_formula_sum            'C14 H17 N6 O10 P'
_chemical_formula_weight         460.31
_chemical_name_systematic
;
6-Nitrobenzimidazolium dihydrogen phosphate 6-nitrobenzimidazole solvate
dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.73(3)
_cell_angle_beta                 107.10(3)
_cell_angle_gamma                111.66(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4683(19)
_cell_length_b                   9.990(2)
_cell_length_c                   11.407(2)
_cell_measurement_reflns_used    6404
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.10
_cell_volume                     949.5(4)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'Crystal Structure (Rigaku/MSC, 2002)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9332
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.471
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0532P)²+0.7024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                2827
_reflns_number_total             4286
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            wm2359.cif
_cod_data_source_block           I
_cod_original_cell_volume        949.4(3)
_cod_database_code               2226715
_cod_database_fobs_code          2226715
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
P P1 0.46015(8) 0.77962(7) 0.52850(6) 0.03448(19) Uani d . 1 . .
O O1 1.0279(3) 0.6110(3) 0.1175(3) 0.0759(8) Uani d . 1 . .
N N1 0.4441(3) 0.4733(2) 0.2701(2) 0.0392(5) Uani d . 1 . .
H H1A 0.4368 0.4114 0.3221 0.047 Uiso calc R 1 . .
C C1 0.6946(3) 0.4893(3) 0.2258(2) 0.0336(5) Uani d . 1 . .
H H1B 0.7181 0.4226 0.2760 0.040 Uiso calc R 1 . .
O O2 0.9605(3) 0.4445(3) 0.2308(2) 0.0638(6) Uani d . 1 . .
N N2 0.3902(3) 0.6274(2) 0.1497(2) 0.0385(5) Uani d . 1 . .
H H2A 0.3417 0.6800 0.1120 0.046 Uiso calc R 1 . .
C C2 0.5632(3) 0.5227(3) 0.2149(2) 0.0313(5) Uani d . 1 . .
O O3 1.1886(3) 1.0612(3) 0.1237(3) 0.0771(8) Uani d . 1 . .
N N3 0.9352(3) 0.5369(3) 0.1686(2) 0.0447(6) Uani d . 1 . .
C C3 0.5284(3) 0.6217(3) 0.1383(2) 0.0317(5) Uani d . 1 . .
O O4 1.0632(3) 1.1997(3) 0.1303(3) 0.0762(8) Uani d . 1 . .
N N4 1.0431(3) 0.7285(2) 0.4511(2) 0.0379(5) Uani d . 1 . .
C C4 0.6251(3) 0.6929(3) 0.0684(2) 0.0376(6) Uani d . 1 . .
H H4B 0.6011 0.7583 0.0168 0.045 Uiso calc R 1 . .
O O5 0.4699(3) 0.8359(2) 0.40310(18) 0.0489(5) Uani d . 1 . .
H H5A 0.4918 0.9324 0.4014 0.050 Uiso d . 1 . .
N N5 0.8298(3) 0.7543(2) 0.47608(19) 0.0375(5) Uani d . 1 . .
H H5B 0.7499 0.7403 0.5024 0.045 Uiso calc R 1 . .
C C5 0.7570(3) 0.6616(3) 0.0796(2) 0.0376(6) Uani d . 1 . .
H H5C 0.8259 0.7070 0.0355 0.045 Uiso calc R 1 . .
O O6 0.2931(2) 0.6510(2) 0.4983(2) 0.0471(5) Uani d . 1 . .
H H6A 0.1868 0.6647 0.4826 0.050 Uiso d . 1 . .
N N6 1.0976(3) 1.0955(3) 0.1613(2) 0.0492(6) Uani d . 1 . .
C C6 0.7888(3) 0.5623(3) 0.1566(2) 0.0347(6) Uani d . 1 . .
O O7 0.5822(2) 0.7132(2) 0.57244(19) 0.0456(5) Uani d . 1 . .
C C7 0.3444(3) 0.5381(3) 0.2287(3) 0.0425(6) Uani d . 1 . .
H H7B 0.2539 0.5234 0.2518 0.051 Uiso calc R 1 . .
O O8 0.4731(3) 0.8988(2) 0.61749(16) 0.0435(5) Uani d . 1 . .
C C8 1.0885(3) 0.9142(3) 0.3032(2) 0.0367(6) Uani d . 1 . .
H H8B 1.1769 0.9045 0.2902 0.044 Uiso calc R 1 . .
O O9 0.2853(3) 0.8166(3) 0.0119(2) 0.0625(6) Uani d . 1 . .
H H9A 0.2025 0.8421 0.0112 0.050 Uiso d . 1 . .
H H9B 0.3401 0.8590 -0.0339 0.050 Uiso d . 1 . .
C C9 1.0114(3) 0.8331(3) 0.3813(2) 0.0320(5) Uani d . 1 . .
O O10 0.4652(3) 0.9058(3) 0.8556(2) 0.0754(8) Uani d . 1 . .
H H10A 0.4652 0.8914 0.7771 0.050 Uiso d . 1 . .
H H10B 0.5564 0.9646 0.9008 0.050 Uiso d . 1 . .
C C10 0.8767(3) 0.8494(3) 0.3970(2) 0.0322(5) Uani d . 1 . .
C C11 0.8168(3) 0.9477(3) 0.3391(2) 0.0389(6) Uani d . 1 . .
H H11A 0.7279 0.9578 0.3508 0.047 Uiso calc R 1 . .
C C12 0.8942(3) 1.0293(3) 0.2638(2) 0.0401(6) Uani d . 1 . .
H H12A 0.8592 1.0976 0.2244 0.048 Uiso calc R 1 . .
C C13 1.0254(3) 1.0093(3) 0.2469(2) 0.0364(6) Uani d . 1 . .
C C14 0.9324(3) 0.6863(3) 0.5052(2) 0.0387(6) Uani d . 1 . .
H H14A 0.9253 0.6161 0.5585 0.046 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O8 P1 O7 . . 115.73(13) ?
O8 P1 O5 . . 109.95(10) ?
O7 P1 O5 . . 108.51(11) ?
O8 P1 O6 . . 110.30(12) ?
O7 P1 O6 . . 105.62(11) ?
O5 P1 O6 . . 106.23(13) ?
C7 N1 C2 . . 107.7(2) ?
C7 N1 H1A . . 126.2 ?
C2 N1 H1A . . 126.2 ?
C2 C1 C6 . . 114.8(2) ?
C2 C1 H1B . . 122.6 ?
C6 C1 H1B . . 122.6 ?
C7 N2 C3 . . 108.4(2) ?
C7 N2 H2A . . 125.8 ?
C3 N2 H2A . . 125.8 ?
C1 C2 N1 . . 131.2(2) ?
C1 C2 C3 . . 122.0(2) ?
N1 C2 C3 . . 106.8(2) ?
O1 N3 O2 . . 122.8(3) ?
O1 N3 C6 . . 118.4(2) ?
O2 N3 C6 . . 118.8(2) ?
N2 C3 C2 . . 106.2(2) ?
N2 C3 C4 . . 131.9(2) ?
C2 C3 C4 . . 121.9(2) ?
C14 N4 C9 . . 104.8(2) ?
C5 C4 C3 . . 116.5(2) ?
C5 C4 H4B . . 121.8 ?
C3 C4 H4B . . 121.8 ?
P1 O5 H5A . . 115.9 ?
C14 N5 C10 . . 107.1(2) ?
C14 N5 H5B . . 126.5 ?
C10 N5 H5B . . 126.5 ?
C4 C5 C6 . . 120.4(2) ?
C4 C5 H5C . . 119.8 ?
C6 C5 H5C . . 119.8 ?
P1 O6 H6A . . 123.8 ?
O3 N6 O4 . . 122.7(3) ?
O3 N6 C13 . . 118.9(3) ?
O4 N6 C13 . . 118.4(2) ?
C1 C6 C5 . . 124.3(2) ?
C1 C6 N3 . . 117.6(2) ?
C5 C6 N3 . . 118.0(2) ?
N1 C7 N2 . . 110.9(2) ?
N1 C7 H7B . . 124.5 ?
N2 C7 H7B . . 124.5 ?
C13 C8 C9 . . 115.7(2) ?
C13 C8 H8B . . 122.2 ?
C9 C8 H8B . . 122.2 ?
H9A O9 H9B . . 116.1 ?
N4 C9 C8 . . 130.5(2) ?
N4 C9 C10 . . 109.0(2) ?
C8 C9 C10 . . 120.4(2) ?
H10A O10 H10B . . 110.3 ?
N5 C10 C11 . . 132.1(2) ?
N5 C10 C9 . . 105.6(2) ?
C11 C10 C9 . . 122.3(2) ?
C12 C11 C10 . . 117.3(2) ?
C12 C11 H11A . . 121.4 ?
C10 C11 H11A . . 121.4 ?
C11 C12 C13 . . 119.7(3) ?
C11 C12 H12A . . 120.1 ?
C13 C12 H12A . . 120.1 ?
C8 C13 C12 . . 124.6(2) ?
C8 C13 N6 . . 118.7(2) ?
C12 C13 N6 . . 116.7(2) ?
N4 C14 N5 . . 113.5(2) ?
N4 C14 H14A . . 123.3 ?
N5 C14 H14A . . 123.3 ?
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
P1 O8 . 1.500(2) y
P1 O7 . 1.504(2) y
P1 O5 . 1.5591(19) y
P1 O6 . 1.562(2) y
O1 N3 . 1.221(3) ?
N1 C7 . 1.315(4) ?
N1 C2 . 1.388(3) ?
N1 H1A . 0.8600 ?
C1 C2 . 1.376(3) ?
C1 C6 . 1.378(3) ?
C1 H1B . 0.9300 ?
O2 N3 . 1.221(3) ?
N2 C7 . 1.328(3) ?
N2 C3 . 1.374(3) ?
N2 H2A . 0.8600 ?
C2 C3 . 1.393(3) ?
O3 N6 . 1.215(3) ?
N3 C6 . 1.467(3) ?
C3 C4 . 1.394(4) ?
O4 N6 . 1.228(3) ?
N4 C14 . 1.310(3) ?
N4 C9 . 1.388(3) ?
C4 C5 . 1.367(4) ?
C4 H4B . 0.9300 ?
O5 H5A . 0.9100 ?
N5 C14 . 1.348(4) ?
N5 C10 . 1.364(3) ?
N5 H5B . 0.8600 ?
C5 C6 . 1.391(4) ?
C5 H5C . 0.9300 ?
O6 H6A . 1.0287 ?
N6 C13 . 1.463(3) ?
C7 H7B . 0.9300 ?
C8 C13 . 1.371(4) ?
C8 C9 . 1.396(3) ?
C8 H8B . 0.9300 ?
O9 H9A . 0.9074 ?
O9 H9B . 0.8512 ?
C9 C10 . 1.405(3) ?
O10 H10A . 0.9048 ?
O10 H10B . 0.8438 ?
C10 C11 . 1.389(4) ?
C11 C12 . 1.373(4) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.395(4) ?
C12 H12A . 0.9300 ?
C14 H14A . 0.9300 ?
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
N1 H1A O7 2_666 0.86 1.74 2.600(2) 179 yes
N2 H2A O9 1_555 0.86 1.92 2.752(2) 164 yes
O6 H6A N4 1_455 1.03 1.66 2.665(2) 165 yes
O5 H5A O8 2_676 0.91 1.62 2.531(2) 174 yes
N5 H5B O7 1_555 0.86 1.91 2.773(2) 176 yes
O9 H9A O3 1_455 0.91 2.59 3.269(2) 132 no
O9 H9A O4 2_675 0.91 2.43 3.161(2) 137 yes
O9 H9B O10 1_554 0.85 1.92 2.754(2) 165 yes
O10 H10A O8 1_555 0.91 1.85 2.740(2) 169 yes
O10 H10B O9 2_676 0.84 2.16 2.917(2) 149 yes
O10 H10B O3 2_776 0.84 2.61 3.106(2) 119 no
