#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/00/2220054.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_2220054
loop_
_publ_author_name
'Zhan, Cai-Hong'
'Zhang, Shu-Guang'
'Feng, Yun-Long'
_publ_section_title
;
 [1-(4-Hydroxyphenyl)-1H-tetrazol-5-ylsulfanyl]acetic acid
;
_journal_coeditor_code           AT2673
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2451
_journal_paper_doi               10.1107/S1600536808037136
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C9 H8 N4 O3 S'
_chemical_formula_moiety         'C9 H8 N4 O3 S'
_chemical_formula_sum            'C9 H8 N4 O3 S'
_chemical_formula_weight         252.25
_chemical_name_systematic
;
[1-(4-Hydroxyphenyl)-1H-tetrazol-5-ylsulfanyl]acetic acid
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.407(3)
_cell_length_b                   7.3365(16)
_cell_length_c                   21.107(5)
_cell_measurement_reflns_used    2531
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.39
_cell_volume                     2230.9(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII area-detector'
_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  0.0991
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18595
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.213
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0144P)²+1.7635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                1834
_reflns_number_total             2550
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2673.cif
_cod_data_source_block           I
_cod_original_cell_volume        2231.0(9)
_cod_database_code               2220054
_cod_database_fobs_code          2220054
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
S S1 0.51454(4) 0.15070(9) 0.09961(3) 0.05074(19) Uani d . 1
O O1 0.15861(13) 0.3256(3) 0.28120(9) 0.0610(5) Uani d D 1
H H1 0.177(2) 0.270(4) 0.3133(11) 0.073 Uiso d D 1
O O2 0.75012(12) 0.0102(3) 0.01914(8) 0.0551(5) Uani d D 1
H H2 0.8048(13) 0.010(4) 0.0322(13) 0.066 Uiso d D 1
O O3 0.72494(12) 0.1471(3) 0.11139(8) 0.0645(5) Uani d . 1
N N1 0.45507(13) 0.4915(3) 0.12461(10) 0.0468(5) Uani d . 1
N N2 0.47350(16) 0.6679(3) 0.10961(12) 0.0637(6) Uani d . 1
N N3 0.54403(16) 0.6653(3) 0.07237(12) 0.0619(6) Uani d . 1
N N4 0.57366(13) 0.4912(3) 0.06208(10) 0.0480(5) Uani d . 1
C C1 0.23393(16) 0.3617(3) 0.24421(11) 0.0441(5) Uani d . 1
C C2 0.21686(16) 0.4284(3) 0.18436(12) 0.0470(6) Uani d . 1
H H2A 0.1561 0.4457 0.1708 0.056 Uiso calc R 1
C C3 0.28941(16) 0.4695(3) 0.14462(12) 0.0478(6) Uani d . 1
H H3A 0.2783 0.5152 0.1042 0.057 Uiso calc R 1
C C4 0.37920(15) 0.4418(3) 0.16560(11) 0.0436(5) Uani d . 1
C C5 0.39734(17) 0.3749(4) 0.22511(12) 0.0509(6) Uani d . 1
H H5A 0.4582 0.3576 0.2386 0.061 Uiso calc R 1
C C6 0.32408(17) 0.3336(4) 0.26463(12) 0.0509(6) Uani d . 1
H H6A 0.3352 0.2870 0.3049 0.061 Uiso calc R 1
C C7 0.51693(14) 0.3855(3) 0.09473(11) 0.0402(5) Uani d . 1
C C8 0.59818(15) 0.0925(3) 0.03998(12) 0.0465(6) Uani d . 1
H H8A 0.5826 -0.0265 0.0231 0.056 Uiso calc R 1
H H8B 0.5931 0.1797 0.0056 0.056 Uiso calc R 1
C C9 0.69718(16) 0.0887(3) 0.06206(11) 0.0429(5) 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'
S S 0.1246 0.1234 '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
C7 S1 C8 100.49(11)
C1 O1 H1 108(2)
C9 O2 H2 109(2)
C7 N1 N2 108.24(19)
C7 N1 C4 129.8(2)
N2 N1 C4 121.94(19)
N3 N2 N1 106.4(2)
N2 N3 N4 111.0(2)
C7 N4 N3 105.86(19)
O1 C1 C2 116.9(2)
O1 C1 C6 122.7(2)
C2 C1 C6 120.4(2)
C3 C2 C1 120.2(2)
C3 C2 H2A 119.9
C1 C2 H2A 119.9
C2 C3 C4 119.0(2)
C2 C3 H3A 120.5
C4 C3 H3A 120.5
C5 C4 C3 121.6(2)
C5 C4 N1 119.7(2)
C3 C4 N1 118.7(2)
C4 C5 C6 119.1(2)
C4 C5 H5A 120.5
C6 C5 H5A 120.5
C5 C6 C1 119.8(2)
C5 C6 H6A 120.1
C1 C6 H6A 120.1
N4 C7 N1 108.4(2)
N4 C7 S1 129.03(18)
N1 C7 S1 122.53(17)
C9 C8 S1 115.16(17)
C9 C8 H8A 108.5
S1 C8 H8A 108.5
C9 C8 H8B 108.5
S1 C8 H8B 108.5
H8A C8 H8B 107.5
O3 C9 O2 124.2(2)
O3 C9 C8 125.6(2)
O2 C9 C8 110.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.726(2)
S1 C8 1.794(2)
O1 C1 1.363(3)
O1 H1 0.835(17)
O2 C9 1.317(3)
O2 H2 0.834(17)
O3 C9 1.195(3)
N1 C7 1.341(3)
N1 N2 1.359(3)
N1 C4 1.441(3)
N2 N3 1.285(3)
N3 N4 1.364(3)
N4 C7 1.321(3)
C1 C2 1.377(3)
C1 C6 1.384(3)
C2 C3 1.374(3)
C2 H2A 0.9300
C3 C4 1.382(3)
C3 H3A 0.9300
C4 C5 1.374(3)
C5 C6 1.379(3)
C5 H5A 0.9300
C6 H6A 0.9300
C8 C9 1.501(3)
C8 H8A 0.9700
C8 H8B 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 H1 O3 6_556 0.835(17) 1.953(17) 2.787(3) 177(3)
O2 H2 N4 8_755 0.834(17) 1.866(17) 2.699(3) 176(3)
O2 H2 N3 8_755 0.834(17) 2.60(2) 3.369(3) 154(3)
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
C7 N1 N2 N3 -0.2(3)
C4 N1 N2 N3 -179.5(2)
N1 N2 N3 N4 -0.2(3)
N2 N3 N4 C7 0.5(3)
O1 C1 C2 C3 179.4(2)
C6 C1 C2 C3 -0.7(4)
C1 C2 C3 C4 0.4(4)
C2 C3 C4 C5 -0.2(4)
C2 C3 C4 N1 -177.7(2)
C7 N1 C4 C5 70.7(3)
N2 N1 C4 C5 -110.2(3)
C7 N1 C4 C3 -111.7(3)
N2 N1 C4 C3 67.4(3)
C3 C4 C5 C6 0.3(4)
N1 C4 C5 C6 177.9(2)
C4 C5 C6 C1 -0.7(4)
O1 C1 C6 C5 -179.3(2)
C2 C1 C6 C5 0.9(4)
N3 N4 C7 N1 -0.6(3)
N3 N4 C7 S1 177.64(19)
N2 N1 C7 N4 0.5(3)
C4 N1 C7 N4 179.7(2)
N2 N1 C7 S1 -177.85(18)
C4 N1 C7 S1 1.3(3)
C8 S1 C7 N4 -7.9(2)
C8 S1 C7 N1 170.13(19)
C7 S1 C8 C9 86.2(2)
S1 C8 C9 O3 -12.3(4)
S1 C8 C9 O2 167.39(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24738915
