#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/45/2234568.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_2234568
loop_
_publ_author_name
'Zhang, Guo-Chun'
'Qiao, Cheng-Fang'
'Zhou, Chun-Sheng'
'Xia, Zheng-Qiang'
_publ_section_title
;
 2-(5-Amino-2H-tetrazol-2-yl)acetic acid
;
_journal_coeditor_code           CV5277
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1330
_journal_paper_doi               10.1107/S1600536812014389
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C3 H5 N5 O2'
_chemical_formula_moiety         'C3 H5 N5 O2'
_chemical_formula_sum            'C3 H5 N5 O2'
_chemical_formula_weight         143.12
_chemical_name_systematic
;
2-(5-Amino-2H-tetrazol-2-yl)acetic acid
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.850(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.381(4)
_cell_length_b                   4.4429(9)
_cell_length_c                   14.846(3)
_cell_measurement_reflns_used    734
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.24
_cell_measurement_theta_min      3.50
_cell_volume                     1212.3(4)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3040
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0657P)²+0.3572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                890
_reflns_number_total             1193
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5277.cif
_cod_data_source_block           I
_cod_original_cell_volume        1212.2(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2234568
_cod_database_fobs_code          2234568
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_symmetry_multiplicity
O O2 0.17856(8) 0.1746(3) 0.30324(8) 0.0527(4) Uani d . 1 1
H H2 0.1626 0.2644 0.3470 0.079 Uiso calc R 1 1
N N2 0.18104(10) 0.4658(4) 0.01590(11) 0.0493(5) Uani d . 1 1
N N3 0.15090(8) 0.2586(4) 0.06465(10) 0.0414(4) Uani d . 1 1
C C3 0.14844(11) 0.2824(5) 0.22938(12) 0.0426(5) Uani d . 1 1
N N4 0.08911(9) 0.1468(4) 0.03036(11) 0.0485(5) Uani d . 1 1
N N1 0.13778(10) 0.4994(4) -0.05556(11) 0.0500(5) Uani d . 1 1
C C2 0.18346(11) 0.1507(5) 0.14771(12) 0.0449(5) Uani d . 1 1
H H2A 0.2348 0.2010 0.1487 0.054 Uiso calc R 1 1
H H2B 0.1793 -0.0668 0.1499 0.054 Uiso calc R 1 1
O O1 0.10122(10) 0.4680(4) 0.22631(10) 0.0752(6) Uani d . 1 1
C C1 0.08229(11) 0.3035(5) -0.04569(13) 0.0479(5) Uani d . 1 1
N N5 0.02757(11) 0.2722(6) -0.10567(13) 0.0787(8) Uani d . 1 1
H H5A -0.0064 0.1434 -0.0962 0.094 Uiso calc R 1 1
H H5B 0.0264 0.3809 -0.1536 0.094 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O2 0.0661(10) 0.0609(10) 0.0308(8) 0.0097(8) -0.0064(6) -0.0009(6)
N2 0.0611(10) 0.0547(11) 0.0320(9) -0.0062(9) -0.0015(7) 0.0015(7)
N3 0.0464(9) 0.0479(10) 0.0300(8) 0.0011(7) 0.0009(7) -0.0019(7)
C3 0.0479(11) 0.0467(12) 0.0329(10) 0.0005(10) -0.0036(8) -0.0002(8)
N4 0.0490(9) 0.0622(11) 0.0341(9) -0.0039(8) -0.0029(7) 0.0042(8)
N1 0.0604(11) 0.0588(12) 0.0309(9) -0.0029(9) -0.0027(7) 0.0027(7)
C2 0.0506(11) 0.0502(12) 0.0337(10) 0.0068(10) -0.0047(8) 0.0013(8)
O1 0.0878(12) 0.0979(14) 0.0398(9) 0.0459(11) -0.0038(8) -0.0048(8)
C1 0.0483(11) 0.0651(14) 0.0303(10) 0.0030(10) 0.0015(8) 0.0015(9)
N5 0.0607(12) 0.125(2) 0.0503(12) -0.0216(12) -0.0165(9) 0.0320(12)
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
C3 O2 H2 109.5
N3 N2 N1 105.66(16)
N2 N3 N4 114.75(16)
N2 N3 C2 122.39(16)
N4 N3 C2 122.81(17)
O1 C3 O2 125.45(18)
O1 C3 C2 123.87(18)
O2 C3 C2 110.64(17)
C1 N4 N3 101.42(17)
N2 N1 C1 106.60(16)
N3 C2 C3 112.53(16)
N3 C2 H2A 109.1
C3 C2 H2A 109.1
N3 C2 H2B 109.1
C3 C2 H2B 109.1
H2A C2 H2B 107.8
N4 C1 N5 124.7(2)
N4 C1 N1 111.56(17)
N5 C1 N1 123.72(19)
C1 N5 H5A 120.0
C1 N5 H5B 120.0
H5A N5 H5B 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C3 1.312(2)
O2 H2 0.8200
N2 N3 1.300(2)
N2 N1 1.325(2)
N3 N4 1.334(2)
N3 C2 1.444(2)
C3 O1 1.198(2)
C3 C2 1.500(3)
N4 C1 1.331(3)
N1 C1 1.351(3)
C2 H2A 0.9700
C2 H2B 0.9700
C1 N5 1.341(2)
N5 H5A 0.8600
N5 H5B 0.8600
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
N5 H5B O1 6_565 0.86 2.36 3.080(3) 140.9
N5 H5A N4 5 0.86 2.23 3.064(3) 163.2
O2 H2 N1 6_566 0.82 1.85 2.665(2) 172.2
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
N1 N2 N3 N4 0.2(2)
N1 N2 N3 C2 177.93(17)
N2 N3 N4 C1 -0.1(2)
C2 N3 N4 C1 -177.82(17)
N3 N2 N1 C1 -0.2(2)
N2 N3 C2 C3 101.8(2)
N4 N3 C2 C3 -80.6(2)
O1 C3 C2 N3 -3.6(3)
O2 C3 C2 N3 178.80(17)
N3 N4 C1 N5 179.7(2)
N3 N4 C1 N1 0.0(2)
N2 N1 C1 N4 0.2(2)
N2 N1 C1 N5 -179.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3125807
