#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/21/2222143.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_2222143
loop_
_publ_author_name
'Dai, Jing'
_publ_section_title
;
 2-(2-Pyrrolidinio)-1H-benzimidazol-3-ium dinitrate
;
_journal_coeditor_code           SJ2610
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1360
_journal_paper_doi               10.1107/S1600536809018558
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H15 N3 2+ , 2N O3 -'
_chemical_formula_moiety         'C11 H15 N3 2+ , 2N O3 -'
_chemical_formula_sum            'C11 H15 N5 O6'
_chemical_formula_weight         313.28
_chemical_name_systematic
;
2-(2-Pyrrolidinio)-1H-benzimidazol-3-ium dinitrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.000
_cell_angle_beta                 127.180(10)
_cell_angle_gamma                90.000
_cell_formula_units_Z            8
_cell_length_a                   22.078(2)
_cell_length_b                   11.1540(10)
_cell_length_c                   14.6700(10)
_cell_measurement_reflns_used    3275
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.19
_cell_volume                     2878.3(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       ω
_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  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14543
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0493P)²+2.1933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1440
_reflns_number_gt                2195
_reflns_number_total             3276
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2610.cif
_cod_data_source_block           I
_cod_original_cell_volume        2878.3(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2222143
_cod_database_fobs_code          2222143
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'
'-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_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
N N3 0.66938(10) 0.39290(15) 0.56483(15) 0.0433(4) Uani d . 1 . .
H H3A 0.6966 0.3290 0.5937 0.052 Uiso calc R 1 . .
N N4 0.63804(11) 0.58040(17) 0.53606(17) 0.0513(5) Uani d . 1 . .
H H4A 0.6414 0.6572 0.5428 0.062 Uiso calc R 1 . .
N N5 0.83307(9) 0.45350(16) 0.71441(14) 0.0429(4) Uani d . 1 . .
H H5A 0.8163 0.4119 0.6506 0.052 Uiso calc R 1 . .
H H5B 0.8425 0.4016 0.7686 0.052 Uiso calc R 1 . .
C C1 0.57133(13) 0.5163(2) 0.4595(2) 0.0500(6) Uani d . 1 . .
C C2 0.49697(15) 0.5521(3) 0.3784(3) 0.0709(8) Uani d . 1 . .
H H2 0.4832 0.6325 0.3664 0.085 Uiso calc R 1 . .
C C3 0.44437(16) 0.4628(3) 0.3162(3) 0.0778(9) Uani d . 1 . .
H H3 0.3939 0.4834 0.2599 0.093 Uiso calc R 1 . .
C C4 0.46486(16) 0.3430(3) 0.3353(2) 0.0725(8) Uani d . 1 . .
H H4 0.4273 0.2856 0.2920 0.087 Uiso calc R 1 . .
C C5 0.53812(15) 0.3057(2) 0.4155(2) 0.0593(7) Uani d . 1 . .
H H5 0.5513 0.2250 0.4276 0.071 Uiso calc R 1 . .
C C6 0.59181(12) 0.3961(2) 0.47789(19) 0.0448(5) Uani d . 1 . .
C C7 0.69499(12) 0.50468(19) 0.59632(18) 0.0418(5) Uani d . 1 . .
C C8 0.77457(13) 0.54335(19) 0.6904(2) 0.0465(6) Uani d . 1 . .
H H8 0.7785 0.5530 0.7602 0.056 Uiso calc R 1 . .
C C9 0.80026(15) 0.6590(2) 0.6698(2) 0.0616(7) Uani d . 1 . .
H H9A 0.7799 0.7281 0.6831 0.074 Uiso calc R 1 . .
H H9B 0.7852 0.6626 0.5926 0.074 Uiso calc R 1 . .
C C10 0.88635(15) 0.6521(2) 0.7577(2) 0.0617(7) Uani d . 1 . .
H H10A 0.9112 0.7044 0.7367 0.074 Uiso calc R 1 . .
H H10B 0.9022 0.6745 0.8331 0.074 Uiso calc R 1 . .
C C11 0.90467(14) 0.5220(2) 0.7552(2) 0.0556(6) Uani d . 1 . .
H H11A 0.9471 0.4953 0.8308 0.067 Uiso calc R 1 . .
H H11B 0.9174 0.5107 0.7030 0.067 Uiso calc R 1 . .
O O1 0.64618(11) 0.82051(14) 0.60914(14) 0.0612(5) Uani d . 1 . .
O O2 0.58007(14) 0.83408(18) 0.42662(16) 0.0852(7) Uani d . 1 . .
O O3 0.59348(11) 0.98868(15) 0.52487(15) 0.0672(5) Uani d . 1 . .
N N1 0.60605(11) 0.88315(18) 0.51830(16) 0.0492(5) Uani d . 1 . .
O O4 0.74570(10) 0.68205(14) 0.85048(13) 0.0533(4) Uani d . 1 . .
O O5 0.81397(9) 0.66960(14) 1.03479(13) 0.0513(4) Uani d . 1 . .
O O6 0.74016(11) 0.52300(15) 0.93113(17) 0.0698(5) Uani d . 1 . .
N N2 0.76639(11) 0.62317(16) 0.93912(16) 0.0447(5) Uani d . 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'
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
C7 N3 C6 . . 108.93(18) ?
C7 N3 H3A . . 125.5 ?
C6 N3 H3A . . 125.5 ?
C7 N4 C1 . . 109.12(19) ?
C7 N4 H4A . . 125.4 ?
C1 N4 H4A . . 125.4 ?
C8 N5 C11 . . 107.51(17) ?
C8 N5 H5A . . 110.2 ?
C11 N5 H5A . . 110.2 ?
C8 N5 H5B . . 110.2 ?
C11 N5 H5B . . 110.2 ?
H5A N5 H5B . . 108.5 ?
C2 C1 C6 . . 121.6(2) ?
C2 C1 N4 . . 132.3(2) ?
C6 C1 N4 . . 106.1(2) ?
C3 C2 C1 . . 116.8(3) ?
C3 C2 H2 . . 121.6 ?
C1 C2 H2 . . 121.6 ?
C2 C3 C4 . . 121.5(3) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C5 C4 C3 . . 122.7(3) ?
C5 C4 H4 . . 118.7 ?
C3 C4 H4 . . 118.7 ?
C4 C5 C6 . . 116.0(3) ?
C4 C5 H5 . . 122.0 ?
C6 C5 H5 . . 122.0 ?
N3 C6 C1 . . 106.27(19) ?
N3 C6 C5 . . 132.2(2) ?
C1 C6 C5 . . 121.5(2) ?
N4 C7 N3 . . 109.58(19) ?
N4 C7 C8 . . 123.10(19) ?
N3 C7 C8 . . 127.21(19) ?
N5 C8 C7 . . 112.84(17) ?
N5 C8 C9 . . 104.12(19) ?
C7 C8 C9 . . 115.8(2) ?
N5 C8 H8 . . 107.9 ?
C7 C8 H8 . . 107.9 ?
C9 C8 H8 . . 107.9 ?
C8 C9 C10 . . 102.4(2) ?
C8 C9 H9A . . 111.3 ?
C10 C9 H9A . . 111.3 ?
C8 C9 H9B . . 111.3 ?
C10 C9 H9B . . 111.3 ?
H9A C9 H9B . . 109.2 ?
C11 C10 C9 . . 104.05(19) ?
C11 C10 H10A . . 110.9 ?
C9 C10 H10A . . 110.9 ?
C11 C10 H10B . . 110.9 ?
C9 C10 H10B . . 110.9 ?
H10A C10 H10B . . 109.0 ?
C10 C11 N5 . . 105.2(2) ?
C10 C11 H11A . . 110.7 ?
N5 C11 H11A . . 110.7 ?
C10 C11 H11B . . 110.7 ?
N5 C11 H11B . . 110.7 ?
H11A C11 H11B . . 108.8 ?
O3 N1 O2 . . 122.4(2) ?
O3 N1 O1 . . 119.45(19) ?
O2 N1 O1 . . 118.1(2) ?
O6 N2 O5 . . 120.74(19) ?
O6 N2 O4 . . 120.96(19) ?
O5 N2 O4 . . 118.29(18) ?
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
N3 C7 . 1.331(3) ?
N3 C6 . 1.386(3) ?
N3 H3A . 0.8600 ?
N4 C7 . 1.316(3) ?
N4 C1 . 1.393(3) ?
N4 H4A . 0.8600 ?
N5 C8 . 1.499(3) ?
N5 C11 . 1.516(3) ?
N5 H5A . 0.9000 ?
N5 H5B . 0.9000 ?
C1 C2 . 1.382(4) ?
C1 C6 . 1.388(3) ?
C2 C3 . 1.375(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.384(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.369(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.396(3) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.499(3) ?
C8 C9 . 1.511(3) ?
C8 H8 . 0.9800 ?
C9 C10 . 1.523(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.514(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
O1 N1 . 1.274(2) ?
O2 N1 . 1.227(2) ?
O3 N1 . 1.226(2) ?
O4 N2 . 1.270(2) ?
O5 N2 . 1.249(2) ?
O6 N2 . 1.231(2) ?
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
N3 H3A O4 4_646 0.86 1.93 2.788(2) 176.6
N3 H3A O5 4_646 0.86 2.50 3.020(2) 119.9
N5 H5B O1 4_646 0.90 1.89 2.771(2) 167.2
N5 H5B O3 4_646 0.90 2.64 3.149(2) 117.1
N5 H5A O5 6_565 0.90 1.90 2.768(2) 161.6
N4 H4A O1 . 0.86 2.04 2.850(2) 157.1
N4 H4A O2 . 0.86 2.42 3.121(3) 139.3
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N4 C1 C2 . . . . -180.0(3) ?
C7 N4 C1 C6 . . . . 0.2(3) ?
C6 C1 C2 C3 . . . . -0.4(4) ?
N4 C1 C2 C3 . . . . 179.8(3) ?
C1 C2 C3 C4 . . . . 1.0(4) ?
C2 C3 C4 C5 . . . . -0.9(5) ?
C3 C4 C5 C6 . . . . 0.1(4) ?
C7 N3 C6 C1 . . . . -1.0(2) ?
C7 N3 C6 C5 . . . . -180.0(2) ?
C2 C1 C6 N3 . . . . -179.4(2) ?
N4 C1 C6 N3 . . . . 0.5(2) ?
C2 C1 C6 C5 . . . . -0.3(4) ?
N4 C1 C6 C5 . . . . 179.6(2) ?
C4 C5 C6 N3 . . . . 179.2(2) ?
C4 C5 C6 C1 . . . . 0.4(4) ?
C1 N4 C7 N3 . . . . -0.9(3) ?
C1 N4 C7 C8 . . . . -177.2(2) ?
C6 N3 C7 N4 . . . . 1.2(3) ?
C6 N3 C7 C8 . . . . 177.4(2) ?
C11 N5 C8 C7 . . . . 149.12(19) ?
C11 N5 C8 C9 . . . . 22.8(2) ?
N4 C7 C8 N5 . . . . -157.4(2) ?
N3 C7 C8 N5 . . . . 26.9(3) ?
N4 C7 C8 C9 . . . . -37.6(3) ?
N3 C7 C8 C9 . . . . 146.7(2) ?
N5 C8 C9 C10 . . . . -38.4(2) ?
C7 C8 C9 C10 . . . . -162.8(2) ?
C8 C9 C10 C11 . . . . 39.8(3) ?
C9 C10 C11 N5 . . . . -25.8(3) ?
C8 N5 C11 C10 . . . . 2.0(2) ?
