#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/99/2219944.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_2219944
loop_
_publ_author_name
'Dai, Jing'
'Wen, Xiao-Chun'
_publ_section_title
;
 2-(2H-Tetrazol-5-yl)pyridinium chloride
;
_journal_coeditor_code           NC2115
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2113
_journal_paper_doi               10.1107/S1600536808032649
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C6 H6 N5 + , Cl -'
_chemical_formula_moiety         'C6 H6 N5 + , Cl -'
_chemical_formula_sum            'C6 H6 Cl N5'
_chemical_formula_weight         183.61
_chemical_name_systematic
;
2-(2H-Tetrazol-5-yl)pyridinium chloride
;
_space_group_IT_number           57
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   16.375(3)
_cell_length_b                   15.313(3)
_cell_length_c                   6.5176(13)
_cell_measurement_reflns_used    2986
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.4758
_cell_measurement_theta_min      2.4875
_cell_volume                     1634.3(5)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16127
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.233
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0619
_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)+(0.0616P)²+0.4596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1482
_reflns_number_gt                1511
_reflns_number_total             2041
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2115.cif
_cod_data_source_block           I
_cod_database_code               2219944
_cod_database_fobs_code          2219944
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y-1/2, 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
C C9 0.0640(2) 0.4651(2) 0.2500 0.0494(10) Uani d S 1
H H9 0.0803 0.5232 0.2500 0.059 Uiso calc SR 1
N N6 0.26721(19) 0.3543(2) 0.2500 0.0476(8) Uani d S 1
N N7 0.33865(17) 0.3973(2) 0.2500 0.0466(8) Uani d S 1
N N8 0.3269(2) 0.4819(3) 0.2500 0.0568(9) Uani d S 1
N N9 0.24511(18) 0.4938(2) 0.2500 0.0480(8) Uani d S 1
H H9A 0.2202 0.5432 0.2500 0.058 Uiso calc SR 1
C C7 0.2096(2) 0.4149(2) 0.2500 0.0399(8) Uani d S 1
C C8 0.1215(2) 0.3988(2) 0.2500 0.0373(8) Uani d S 1
N N10 0.09641(17) 0.31585(19) 0.2500 0.0422(8) Uani d S 1
H H10A 0.1325 0.2750 0.2500 0.051 Uiso calc SR 1
C C12 0.0174(2) 0.2938(3) 0.2500 0.0516(10) Uani d S 1
H H12 0.0025 0.2352 0.2500 0.062 Uiso calc SR 1
C C11 -0.0412(3) 0.3566(3) 0.2500 0.0619(12) Uani d S 1
H H11 -0.0962 0.3414 0.2500 0.074 Uiso calc SR 1
C C10 -0.0181(2) 0.4434(3) 0.2500 0.0566(11) Uani d S 1
H H10 -0.0575 0.4871 0.2500 0.068 Uiso calc SR 1
N N4 0.4116(2) 0.8572(2) 0.2500 0.0671(11) Uani d S 1
N N3 0.3635(2) 0.7880(2) 0.2500 0.0663(10) Uani d S 1
N N2 0.2886(2) 0.8188(2) 0.2500 0.0615(10) Uani d S 1
H H2 0.2462 0.7856 0.2500 0.074 Uiso calc SR 1
N N1 0.2836(2) 0.9048(2) 0.2500 0.0591(10) Uani d S 1
N N5 0.33937(17) 1.0833(2) 0.2500 0.0414(7) Uani d S 1
H H5A 0.2880 1.0714 0.2500 0.050 Uiso calc SR 1
C C1 0.3619(2) 0.9270(2) 0.2500 0.0422(9) Uani d S 1
C C2 0.3931(2) 1.0162(2) 0.2500 0.0373(8) Uani d S 1
C C3 0.4760(2) 1.0352(2) 0.2500 0.0475(9) Uani d S 1
H H3 0.5145 0.9905 0.2500 0.057 Uiso calc SR 1
C C4 0.5005(2) 1.1221(3) 0.2500 0.0533(10) Uani d S 1
H H4 0.5559 1.1355 0.2500 0.064 Uiso calc SR 1
C C5 0.4444(3) 1.1881(3) 0.2500 0.0546(11) Uani d S 1
H H5 0.4611 1.2461 0.2500 0.066 Uiso calc SR 1
C C6 0.3620(2) 1.1670(3) 0.2500 0.0486(9) Uani d S 1
H H6 0.3228 1.2110 0.2500 0.058 Uiso calc SR 1
Cl Cl1 0.15729(5) 0.12495(6) 0.2500 0.0456(3) Uani d S 1
Cl Cl2 0.16485(7) 0.66996(7) 0.2500 0.0764(4) Uani d S 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 C9 C10 119.0(4)
C8 C9 H9 120.5
C10 C9 H9 120.5
C7 N6 N7 106.0(3)
N8 N7 N6 111.0(3)
N7 N8 N9 106.2(3)
C7 N9 N8 108.0(3)
C7 N9 H9A 126.0
N8 N9 H9A 126.0
N6 C7 N9 108.9(3)
N6 C7 C8 125.7(3)
N9 C7 C8 125.4(3)
N10 C8 C9 119.3(3)
N10 C8 C7 117.6(3)
C9 C8 C7 123.1(3)
C8 N10 C12 122.6(3)
C8 N10 H10A 118.7
C12 N10 H10A 118.7
N10 C12 C11 120.3(4)
N10 C12 H12 119.8
C11 C12 H12 119.8
C12 C11 C10 119.1(4)
C12 C11 H11 120.4
C10 C11 H11 120.4
C11 C10 C9 119.8(4)
C11 C10 H10 120.1
C9 C10 H10 120.1
N3 N4 C1 106.1(3)
N2 N3 N4 105.5(3)
N3 N2 N1 114.6(3)
N3 N2 H2 122.7
N1 N2 H2 122.7
N2 N1 C1 101.2(3)
C6 N5 C2 123.3(3)
C6 N5 H5A 118.4
C2 N5 H5A 118.4
N1 C1 N4 112.5(3)
N1 C1 C2 125.3(3)
N4 C1 C2 122.2(3)
N5 C2 C3 118.5(3)
N5 C2 C1 118.9(3)
C3 C2 C1 122.5(3)
C2 C3 C4 118.8(3)
C2 C3 H3 120.6
C4 C3 H3 120.6
C5 C4 C3 121.0(4)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 C6 118.8(4)
C4 C5 H5 120.6
C6 C5 H5 120.6
N5 C6 C5 119.6(4)
N5 C6 H6 120.2
C5 C6 H6 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 C8 1.384(5)
C9 C10 1.385(5)
C9 H9 0.9300
N6 C7 1.324(5)
N6 N7 1.343(4)
N7 N8 1.309(5)
N8 N9 1.352(4)
N9 C7 1.340(4)
N9 H9A 0.8600
C7 C8 1.464(5)
C8 N10 1.334(4)
N10 C12 1.337(4)
N10 H10A 0.8600
C12 C11 1.359(6)
C12 H12 0.9300
C11 C10 1.382(6)
C11 H11 0.9300
C10 H10 0.9300
N4 N3 1.320(5)
N4 C1 1.343(5)
N3 N2 1.315(4)
N2 N1 1.320(4)
N2 H2 0.8600
N1 C1 1.326(5)
N5 C6 1.335(5)
N5 C2 1.351(4)
N5 H5A 0.8600
C1 C2 1.459(5)
C2 C3 1.389(5)
C3 C4 1.390(5)
C3 H3 0.9300
C4 C5 1.365(5)
C4 H4 0.9300
C5 C6 1.387(5)
C5 H5 0.9300
C6 H6 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
N9 H9A Cl2 . 0.86 2.14 3.001(3) 176.8
N10 H10A Cl1 . 0.86 2.33 3.088(3) 146.7
N2 H2 Cl2 . 0.86 2.22 3.050(4) 163.2
N5 H5A Cl1 1_565 0.86 2.29 3.049(3) 146.8
N5 H5A N1 . 0.86 2.55 2.881(4) 103.9
N10 H10A N6 . 0.86 2.52 2.858(4) 104.6
C9 H9 Cl2 . 0.93 2.64 3.545(4) 165.0
C3 H3 N8 4_655 0.93 2.60 3.329(5) 135.6
C6 H6 N6 1_565 0.93 2.38 3.260(5) 158.9
C10 H10 Cl1 4 0.93 2.67 3.596(4) 173.8
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655647
