#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228294.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228294
loop_
_publ_author_name
'Feng, Li-ping'
'Zhao, Liang'
_publ_section_title
;
 5-[1-(Carboxymethyl)pyridinium-4-yl]-1,2,3,4-tetrazol-1-ide
;
_journal_coeditor_code           DN2625
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3310
_journal_paper_doi               10.1107/S1600536810048403
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H7 N5 O2'
_chemical_formula_moiety         'C8 H7 N5 O2'
_chemical_formula_sum            'C8 H7 N5 O2'
_chemical_formula_weight         205.19
_chemical_name_systematic
;
5-[1-(Carboxymethyl)pyridinium-4-yl]-1,2,3,4-tetrazol-1-ide
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 101.80(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8094(18)
_cell_length_b                   9.3732(19)
_cell_length_c                   11.189(2)
_cell_measurement_reflns_used    2059
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.21
_cell_volume                     904.4(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics
'XP in SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            4629
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.000
_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    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1043
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0311
_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)+(0.0478P)²+0.1896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                971
_reflns_number_total             1043
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2625.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2228294
_cod_database_fobs_code          2228294
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'
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 O1 1.1510(2) 0.22028(18) 0.28067(17) 0.0424(4) Uani d . 1 . .
H H1A 1.1988 0.1581 0.2523 0.064 Uiso calc R 1 . .
O O2 0.9872(2) 0.04264(18) 0.30239(18) 0.0473(4) Uani d . 1 . .
N N1 0.83175(19) 0.21616(19) 0.43834(16) 0.0302(4) Uani d . 1 . .
N N2 0.3137(2) 0.1524(3) 0.5601(2) 0.0498(6) Uani d . 1 . .
N N3 0.2244(2) 0.0761(3) 0.6185(2) 0.0488(6) Uani d . 1 . .
N N4 0.2990(2) -0.0370(2) 0.66513(19) 0.0411(5) Uani d . 1 . .
N N5 0.4411(2) -0.0394(2) 0.6403(2) 0.0414(5) Uani d . 1 . .
C C1 0.6906(3) 0.2695(3) 0.3907(2) 0.0374(5) Uani d . 1 . .
H H1 0.6795 0.3366 0.3283 0.045 Uiso calc R 1 . .
C C2 0.5627(3) 0.2256(3) 0.4332(2) 0.0383(5) Uani d . 1 . .
H H2 0.4658 0.2645 0.4011 0.046 Uiso calc R 1 . .
C C3 0.5786(2) 0.1231(2) 0.5242(2) 0.0306(4) Uani d . 1 . .
C C4 0.7249(3) 0.0675(2) 0.5702(2) 0.0371(5) Uani d . 1 . .
H H4 0.7380 -0.0023 0.6304 0.045 Uiso calc R 1 . .
C C5 0.8499(3) 0.1156(2) 0.5265(2) 0.0375(5) Uani d . 1 . .
H H5 0.9480 0.0788 0.5578 0.045 Uiso calc R 1 . .
C C6 0.4446(2) 0.0779(2) 0.57437(19) 0.0320(5) Uani d . 1 . .
C C7 0.9702(2) 0.2699(2) 0.3979(2) 0.0339(5) Uani d . 1 . .
H H7A 1.0494 0.2934 0.4690 0.041 Uiso calc R 1 . .
H H7B 0.9435 0.3567 0.3511 0.041 Uiso calc R 1 . .
C C8 1.0352(2) 0.1622(2) 0.32033(19) 0.0308(4) 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
C8 O1 H1A . . 109.5 ?
C1 N1 C5 . . 120.71(18) ?
C1 N1 C7 . . 120.49(18) ?
C5 N1 C7 . . 118.77(18) ?
N3 N2 C6 . . 104.1(2) ?
N4 N3 N2 . . 109.6(2) ?
N3 N4 N5 . . 110.4(2) ?
C6 N5 N4 . . 103.3(2) ?
N1 C1 C2 . . 120.6(2) ?
N1 C1 H1 . . 119.7 ?
C2 C1 H1 . . 119.7 ?
C1 C2 C3 . . 119.7(2) ?
C1 C2 H2 . . 120.2 ?
C3 C2 H2 . . 120.2 ?
C2 C3 C4 . . 118.6(2) ?
C2 C3 C6 . . 120.81(19) ?
C4 C3 C6 . . 120.52(19) ?
C5 C4 C3 . . 119.8(2) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
N1 C5 C4 . . 120.5(2) ?
N1 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
N5 C6 N2 . . 112.5(2) ?
N5 C6 C3 . . 124.28(19) ?
N2 C6 C3 . . 123.2(2) ?
N1 C7 C8 . . 112.40(17) ?
N1 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
N1 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.9 ?
O2 C8 O1 . . 127.1(2) ?
O2 C8 C7 . . 123.7(2) ?
O1 C8 C7 . . 109.16(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
O1 C8 . 1.311(3) ?
O1 H1A . 0.8200 ?
O2 C8 . 1.200(3) ?
N1 C1 . 1.345(3) ?
N1 C5 . 1.350(3) ?
N1 C7 . 1.474(3) ?
N2 N3 . 1.329(3) ?
N2 C6 . 1.330(3) ?
N3 N4 . 1.299(3) ?
N4 N5 . 1.337(3) ?
N5 C6 . 1.328(3) ?
C1 C2 . 1.373(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.386(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.388(3) ?
C3 C6 . 1.469(3) ?
C4 C5 . 1.370(3) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C7 C8 . 1.517(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
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
O1 H1A N4 2_654 0.82 1.84 2.648(3) 170.4
C1 H1 O2 3_455 0.93 2.55 3.165(3) 124.3
C1 H1 N3 4_554 0.93 2.59 3.440(3) 151.8
C5 H5 N3 1_655 0.93 2.39 3.270(3) 157.7
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
C6 N2 N3 N4 . . . . 0.3(3) ?
N2 N3 N4 N5 . . . . 0.5(3) ?
N3 N4 N5 C6 . . . . -1.0(3) ?
C5 N1 C1 C2 . . . . 1.9(4) ?
C7 N1 C1 C2 . . . . -176.2(2) ?
N1 C1 C2 C3 . . . . -1.5(4) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C1 C2 C3 C6 . . . . 177.9(2) ?
C2 C3 C4 C5 . . . . 0.9(4) ?
C6 C3 C4 C5 . . . . -176.9(2) ?
C1 N1 C5 C4 . . . . -0.9(4) ?
C7 N1 C5 C4 . . . . 177.2(2) ?
C3 C4 C5 N1 . . . . -0.5(4) ?
N4 N5 C6 N2 . . . . 1.3(3) ?
N4 N5 C6 C3 . . . . -179.9(2) ?
N3 N2 C6 N5 . . . . -1.0(3) ?
N3 N2 C6 C3 . . . . -179.9(2) ?
C2 C3 C6 N5 . . . . 164.3(2) ?
C4 C3 C6 N5 . . . . -17.9(3) ?
C2 C3 C6 N2 . . . . -17.0(3) ?
C4 C3 C6 N2 . . . . 160.8(2) ?
C1 N1 C7 C8 . . . . -108.5(2) ?
C5 N1 C7 C8 . . . . 73.4(3) ?
N1 C7 C8 O2 . . . . -5.8(3) ?
N1 C7 C8 O1 . . . . 175.68(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656342
2 PubChem 102508547
