#------------------------------------------------------------------------------
#$Date: 2019-10-28 09:23:29 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219800 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/60/2226071.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_2226071
loop_
_publ_author_name
'Liu, Xin'
'Zhu, Weiqun'
_publ_section_title
;
 4-Nitrobenzoic acid--2,2'-biimidazole (2/1)
;
_journal_coeditor_code           BX2278
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1245
_journal_paper_doi               10.1107/S1600536810015643
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '2C7 H5 N O4, C6 H6 N4'
_chemical_formula_moiety         '2(C7 H5 N O4), C6 H6 N4'
_chemical_formula_sum            'C20 H16 N6 O8'
_chemical_formula_weight         468.38
_chemical_name_systematic
;
4-Nitrobenzoic acid--2,2'-biimidazole (2/1)
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.4960(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.8520(10)
_cell_length_b                   10.9245(10)
_cell_length_c                   19.7981(10)
_cell_measurement_reflns_used    1230
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.00
_cell_measurement_theta_min      2.78
_cell_volume                     1049.4(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_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      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega 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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5185
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.9860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.148
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1340
_reflns_number_gt                1264
_reflns_number_total             1849
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2278.cif
_cod_data_source_block           I
_cod_depositor_comments
;

2019-10-26
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C10 H8 N3 O4'
_cod_original_formula_weight         234.19
_cod_original_formula_moiety         'C7 H5 N O4, 0.5(C6 H6 N4)'
_cod_original_formula_iupac          'C7 H5 N O4, 0.5C6 H6 N4'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226071
_cod_database_fobs_code          2226071
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_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
C C1 0.3475(4) 0.7795(2) 0.58109(11) 0.0548(6) Uani d . 1 . .
C C2 -0.2424(4) 0.54924(18) 0.67279(9) 0.0493(5) Uani d . 1 . .
C C3 -0.1097(4) 0.5072(2) 0.61681(10) 0.0577(6) Uani d . 1 . .
H H3 -0.1475 0.4298 0.5995 0.069 Uiso calc R 1 . .
C C4 0.0825(4) 0.5826(2) 0.58629(11) 0.0586(6) Uani d . 1 . .
H H4 0.1753 0.5557 0.5482 0.070 Uiso calc R 1 . .
C C5 0.1368(4) 0.69760(19) 0.61233(10) 0.0502(5) Uani d . 1 . .
C C6 -0.0063(4) 0.7371(2) 0.66845(10) 0.0565(6) Uani d . 1 . .
H H6 0.0283 0.8148 0.6858 0.068 Uiso calc R 1 . .
C C7 -0.1990(4) 0.66362(19) 0.69917(11) 0.0551(6) Uani d . 1 . .
H H7 -0.2963 0.6908 0.7366 0.066 Uiso calc R 1 . .
C C9 0.9965(4) 0.95887(18) 0.47185(10) 0.0468(5) Uani d . 1 . .
C C10 0.8856(5) 0.8140(2) 0.40287(11) 0.0676(7) Uani d . 1 . .
H H10 0.7961 0.7472 0.3836 0.081 Uiso calc R 1 . .
C C11 1.0980(5) 0.8751(2) 0.37532(11) 0.0678(7) Uani d . 1 . .
H H11 1.1813 0.8580 0.3342 0.081 Uiso calc R 1 . .
H H2A 0.566(4) 0.7886(19) 0.5083(11) 0.080 Uiso d D 1 . .
N N1 0.8218(3) 0.86605(16) 0.46396(9) 0.0549(5) Uani d . 1 . .
N N2 1.1672(3) 0.96604(16) 0.41881(8) 0.0550(5) Uani d . 1 . .
H H2 1.2968 1.0188 0.4135 0.066 Uiso calc R 1 . .
N N3 -0.4451(4) 0.46869(19) 0.70582(9) 0.0596(5) Uani d . 1 . .
O O1 0.4057(3) 0.87721(14) 0.60756(8) 0.0689(5) Uani d . 1 . .
O O2 0.4566(3) 0.73838(16) 0.52653(8) 0.0739(5) Uani d D 1 . .
O O3 -0.5946(4) 0.50989(16) 0.74887(10) 0.0873(6) Uani d . 1 . .
O O4 -0.4548(4) 0.36262(17) 0.68800(10) 0.0926(6) 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'
Cu Cu 0.3201 1.2651 '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
O1 C1 O2 . . 124.7(2) ?
O1 C1 C5 . . 120.1(2) ?
O2 C1 C5 . . 115.2(2) ?
C3 C2 C7 . . 122.95(19) ?
C3 C2 N3 . . 118.65(19) ?
C7 C2 N3 . . 118.40(18) ?
C2 C3 C4 . . 118.5(2) ?
C2 C3 H3 . . 120.7 ?
C4 C3 H3 . . 120.7 ?
C5 C4 C3 . . 120.3(2) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 119.17(19) ?
C4 C5 C1 . . 121.2(2) ?
C6 C5 C1 . . 119.7(2) ?
C7 C6 C5 . . 121.3(2) ?
C7 C6 H6 . . 119.3 ?
C5 C6 H6 . . 119.3 ?
C2 C7 C6 . . 117.76(19) ?
C2 C7 H7 . . 121.1 ?
C6 C7 H7 . . 121.1 ?
N1 C9 N2 . . 110.41(18) ?
N1 C9 C9 . 3_776 125.5(2) ?
N2 C9 C9 . 3_776 124.1(2) ?
C11 C10 N1 . . 109.3(2) ?
C11 C10 H10 . . 125.3 ?
N1 C10 H10 . . 125.3 ?
C10 C11 N2 . . 106.98(19) ?
C10 C11 H11 . . 126.5 ?
N2 C11 H11 . . 126.5 ?
C9 N1 C10 . . 105.70(18) ?
C9 N2 C11 . . 107.60(17) ?
C9 N2 H2 . . 126.2 ?
C11 N2 H2 . . 126.2 ?
O3 N3 O4 . . 122.56(19) ?
O3 N3 C2 . . 119.7(2) ?
O4 N3 C2 . . 117.72(18) ?
C1 O2 H2A . . 113.3(17) ?
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
C1 O1 . 1.222(3) ?
C1 O2 . 1.288(3) ?
C1 C5 . 1.496(3) ?
C2 C3 . 1.366(3) ?
C2 C7 . 1.370(3) ?
C2 N3 . 1.476(3) ?
C3 C4 . 1.387(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.382(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(3) ?
C6 C7 . 1.377(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C9 N1 . 1.330(2) ?
C9 N2 . 1.345(2) ?
C9 C9 3_776 1.432(4) ?
C10 C11 . 1.347(3) ?
C10 N1 . 1.374(3) ?
C10 H10 . 0.9300 ?
C11 N2 . 1.355(3) ?
C11 H11 . 0.9300 ?
N2 H2 . 0.8600 ?
N3 O3 . 1.211(2) ?
N3 O4 . 1.212(2) ?
O2 H2A . 0.845(10) ?
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
O2 H2A N1 . 0.845(10) 1.747(11) 2.580(2) 168(3)
N2 H2 O1 3_776 0.86 1.89 2.742(2) 172.9
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 C2 C3 C4 . . . . 1.6(3) ?
N3 C2 C3 C4 . . . . -179.36(18) ?
C2 C3 C4 C5 . . . . -0.1(3) ?
C3 C4 C5 C6 . . . . -1.1(3) ?
C3 C4 C5 C1 . . . . 178.72(18) ?
O1 C1 C5 C4 . . . . -175.01(18) ?
O2 C1 C5 C4 . . . . 4.7(3) ?
O1 C1 C5 C6 . . . . 4.8(3) ?
O2 C1 C5 C6 . . . . -175.56(18) ?
C4 C5 C6 C7 . . . . 0.7(3) ?
C1 C5 C6 C7 . . . . -179.06(18) ?
C3 C2 C7 C6 . . . . -1.9(3) ?
N3 C2 C7 C6 . . . . 179.04(18) ?
C5 C6 C7 C2 . . . . 0.7(3) ?
N1 C10 C11 N2 . . . . -0.4(3) ?
N2 C9 N1 C10 . . . . -0.6(2) ?
C9 C9 N1 C10 3_776 . . . 178.9(2) ?
C11 C10 N1 C9 . . . . 0.6(3) ?
N1 C9 N2 C11 . . . . 0.4(2) ?
C9 C9 N2 C11 3_776 . . . -179.1(2) ?
C10 C11 N2 C9 . . . . 0.0(2) ?
C3 C2 N3 O3 . . . . -168.9(2) ?
C7 C2 N3 O3 . . . . 10.2(3) ?
C3 C2 N3 O4 . . . . 10.8(3) ?
C7 C2 N3 O4 . . . . -170.2(2) ?
