#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/23/2222308.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_2222308
loop_
_publ_author_name
'Cui, Li-Jing'
_publ_section_title
;
 3-(1H-Tetrazol-5-yl)pyridinium
 3-(2H-tetrazol-5-yl)pyridinium dinitrate
;
_journal_coeditor_code           HB2945
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1684
_journal_paper_doi               10.1107/S160053680901839X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H6 N5 +, N O3 -'
_chemical_formula_moiety         'C6 H6 N5 +, N O3 -'
_chemical_formula_sum            'C6 H6 N6 O3'
_chemical_formula_weight         210.17
_chemical_name_systematic
;
3-(1H-Tetrazol-5-yl)pyridinium 3-(2H-tetrazol-5-yl)pyridinium
dinitrate
;
_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                110.10(3)
_cell_angle_beta                 100.65(3)
_cell_angle_gamma                95.87(3)
_cell_formula_units_Z            4
_cell_length_a                   6.9157(14)
_cell_length_b                   10.575(2)
_cell_length_c                   13.346(3)
_cell_measurement_reflns_used    4035
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.05
_cell_volume                     886.2(4)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       'CCD profile fitting'
_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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9175
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0566
_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)+(0.0621P)²+0.11P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1504
_reflns_number_gt                2272
_reflns_number_total             4035
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2945.cif
_cod_data_source_block           I
_cod_original_cell_volume        886.2(3)
_cod_database_code               2222308
_cod_database_fobs_code          2222308
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
O O4 0.6923(3) 0.42367(18) 0.16340(15) 0.0676(5) Uani d . 1 . .
N N12 0.7836(3) 0.3552(2) 0.09506(16) 0.0538(5) Uani d . 1 . .
O O5 0.8211(3) 0.24401(18) 0.09476(15) 0.0736(5) Uani d . 1 . .
N N5 0.6669(3) 0.30395(19) 0.31822(16) 0.0562(5) Uani d . 1 . .
H H5A 0.6691 0.3510 0.2770 0.067 Uiso calc R 1 . .
O O6 0.8282(3) 0.40305(19) 0.02794(15) 0.0719(5) Uani d . 1 . .
N N6 0.3306(3) 1.0327(2) 0.16715(18) 0.0631(6) Uani d . 1 . .
C C3 0.6604(3) 0.1553(2) 0.44515(18) 0.0521(6) Uani d . 1 . .
H H3 0.6577 0.1028 0.4885 0.063 Uiso calc R 1 . .
N N1 0.2697(3) 0.3533(2) 0.53331(16) 0.0581(5) Uani d . 1 . .
C C5 0.5298(3) 0.3174(2) 0.37811(18) 0.0499(6) Uani d . 1 . .
H H5 0.4387 0.3755 0.3745 0.060 Uiso calc R 1 . .
C C12 0.3716(3) 0.9175(2) 0.17583(18) 0.0478(5) Uani d . 1 . .
C C6 0.3778(3) 0.2557(2) 0.51234(17) 0.0466(5) Uani d . 1 . .
N N9 0.2512(3) 0.8800(2) 0.23196(17) 0.0578(5) Uani d . 1 . .
C C4 0.5260(3) 0.2439(2) 0.44512(17) 0.0446(5) Uani d . 1 . .
C C10 0.5230(3) 0.8456(2) 0.13170(17) 0.0438(5) Uani d . 1 . .
N N2 0.1669(3) 0.3194(3) 0.59678(17) 0.0641(6) Uani d . 1 . .
N N4 0.3414(3) 0.1670(2) 0.56134(18) 0.0687(6) Uani d . 1 . .
N N7 0.1816(3) 1.0644(2) 0.2193(2) 0.0723(6) Uani d . 1 . .
C C11 0.5523(3) 0.7245(2) 0.14313(19) 0.0524(6) Uani d . 1 . .
H H11 0.4782 0.6892 0.1821 0.063 Uiso calc R 1 . .
C C1 0.8009(4) 0.2213(3) 0.3189(2) 0.0607(7) Uani d . 1 . .
H H1 0.8951 0.2166 0.2768 0.073 Uiso calc R 1 . .
N N3 0.2040(4) 0.2098(3) 0.61492(19) 0.0750(7) Uani d . 1 . .
C C2 0.7973(4) 0.1445(2) 0.3817(2) 0.0577(6) Uani d . 1 . .
H H2 0.8872 0.0849 0.3818 0.069 Uiso calc R 1 . .
C C9 0.6383(4) 0.8947(3) 0.0739(2) 0.0609(7) Uani d . 1 . .
H H9 0.6247 0.9778 0.0664 0.073 Uiso calc R 1 . .
N N10 0.6860(3) 0.6578(2) 0.09869(18) 0.0673(6) Uani d . 1 . .
H H10A 0.7034 0.5828 0.1079 0.081 Uiso calc R 1 . .
N N8 0.1327(3) 0.9736(2) 0.25866(19) 0.0722(6) Uani d . 1 . .
C C7 0.7937(4) 0.7011(3) 0.0409(2) 0.0765(8) Uani d . 1 . .
H H7 0.8835 0.6496 0.0096 0.092 Uiso calc R 1 . .
C C8 0.7731(4) 0.8206(3) 0.0275(2) 0.0752(8) Uani d . 1 . .
H H8 0.8490 0.8522 -0.0126 0.090 Uiso calc R 1 . .
N N11 0.7936(3) 0.4430(2) 0.71227(17) 0.0552(5) Uani d . 1 . .
O O3 0.6532(3) 0.4772(2) 0.75145(17) 0.0817(6) Uani d . 1 . .
O O2 0.8610(3) 0.3403(2) 0.71981(19) 0.0878(6) Uani d . 1 . .
O O1 0.8712(3) 0.5025(2) 0.66120(17) 0.0809(6) Uani d . 1 . .
H H9A 0.236(4) 0.802(3) 0.248(2) 0.069(8) Uiso d . 1 . .
H H2A 0.075(4) 0.361(3) 0.625(2) 0.073(9) Uiso 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
O5 N12 O6 . . 122.0(2) ?
O5 N12 O4 . . 120.4(2) ?
O6 N12 O4 . . 117.6(2) ?
C5 N5 C1 . . 123.6(2) ?
C5 N5 H5A . . 118.2 ?
C1 N5 H5A . . 118.2 ?
C12 N6 N7 . . 106.2(2) ?
C2 C3 C4 . . 120.4(2) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
N2 N1 C6 . . 101.2(2) ?
N5 C5 C4 . . 118.8(2) ?
N5 C5 H5 . . 120.6 ?
C4 C5 H5 . . 120.6 ?
N6 C12 N9 . . 108.2(2) ?
N6 C12 C10 . . 125.2(2) ?
N9 C12 C10 . . 126.7(2) ?
N1 C6 N4 . . 112.5(2) ?
N1 C6 C4 . . 125.0(2) ?
N4 C6 C4 . . 122.4(2) ?
C12 N9 N8 . . 108.6(2) ?
C12 N9 H9A . . 129.7(16) ?
N8 N9 H9A . . 121.5(16) ?
C5 C4 C3 . . 118.6(2) ?
C5 C4 C6 . . 120.5(2) ?
C3 C4 C6 . . 120.9(2) ?
C11 C10 C9 . . 117.9(2) ?
C11 C10 C12 . . 120.9(2) ?
C9 C10 C12 . . 121.2(2) ?
N3 N2 N1 . . 114.9(2) ?
N3 N2 H2A . . 118.7(17) ?
N1 N2 H2A . . 126.4(17) ?
N3 N4 C6 . . 105.8(2) ?
N8 N7 N6 . . 110.6(2) ?
N10 C11 C10 . . 120.0(2) ?
N10 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
N5 C1 C2 . . 119.0(2) ?
N5 C1 H1 . . 120.5 ?
C2 C1 H1 . . 120.5 ?
N2 N3 N4 . . 105.6(2) ?
C1 C2 C3 . . 119.6(2) ?
C1 C2 H2 . . 120.2 ?
C3 C2 H2 . . 120.2 ?
C8 C9 C10 . . 120.1(2) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C7 N10 C11 . . 123.0(2) ?
C7 N10 H10A . . 118.5 ?
C11 N10 H10A . . 118.5 ?
N7 N8 N9 . . 106.5(2) ?
N10 C7 C8 . . 119.8(3) ?
N10 C7 H7 . . 120.1 ?
C8 C7 H7 . . 120.1 ?
C7 C8 C9 . . 119.2(3) ?
C7 C8 H8 . . 120.4 ?
C9 C8 H8 . . 120.4 ?
O3 N11 O1 . . 122.8(2) ?
O3 N11 O2 . . 120.1(2) ?
O1 N11 O2 . . 117.1(2) ?
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
O4 N12 . 1.268(2) ?
N12 O5 . 1.229(2) ?
N12 O6 . 1.239(2) ?
N5 C5 . 1.337(3) ?
N5 C1 . 1.338(3) ?
N5 H5A . 0.8600 ?
N6 C12 . 1.317(3) ?
N6 N7 . 1.354(3) ?
C3 C2 . 1.370(3) ?
C3 C4 . 1.386(3) ?
C3 H3 . 0.9300 ?
N1 N2 . 1.315(3) ?
N1 C6 . 1.319(3) ?
C5 C4 . 1.374(3) ?
C5 H5 . 0.9300 ?
C12 N9 . 1.334(3) ?
C12 C10 . 1.450(3) ?
C6 N4 . 1.343(3) ?
C6 C4 . 1.469(3) ?
N9 N8 . 1.345(3) ?
N9 H9A . 0.93(2) ?
C10 C11 . 1.372(3) ?
C10 C9 . 1.385(3) ?
N2 N3 . 1.304(3) ?
N2 H2A . 0.88(3) ?
N4 N3 . 1.318(3) ?
N7 N8 . 1.288(3) ?
C11 N10 . 1.324(3) ?
C11 H11 . 0.9300 ?
C1 C2 . 1.354(3) ?
C1 H1 . 0.9300 ?
C2 H2 . 0.9300 ?
C9 C8 . 1.377(4) ?
C9 H9 . 0.9300 ?
N10 C7 . 1.321(3) ?
N10 H10A . 0.8600 ?
C7 C8 . 1.354(4) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
N11 O3 . 1.215(2) ?
N11 O1 . 1.228(2) ?
N11 O2 . 1.253(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
N9 H9A O2 2_666 0.93(2) 1.80(3) 2.700(3) 164(2)
N2 H2A O1 1_455 0.88(3) 2.16(3) 2.998(3) 161(2)
N2 H2A O2 1_455 0.88(3) 2.16(3) 2.890(3) 140(2)
N5 H5A O4 . 0.86 1.94 2.791(3) 168
N10 H10A O4 . 0.86 2.06 2.891(3) 163
N10 H10A O6 . 0.86 2.19 2.873(3) 137
