#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/80/2238028.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_2238028
loop_
_publ_author_name
'Mafud, Ana C.'
'Mascarenhas, Yvonne P.'
'Nascimento, Alessandro S.'
_publ_section_title
;
 2-({1-[2-(Methylsulfanyl)phenyl]-1H-tetrazol-5-yl}sulfanyl)acetic
 acid
;
_journal_coeditor_code           SU2571
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o759
_journal_paper_doi               10.1107/S160053681300980X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C10 H10 N4 O2 S2'
_chemical_formula_moiety         'C10 H10 N4 O2 S2'
_chemical_formula_sum            'C10 H10 N4 O2 S2'
_chemical_formula_weight         282.34
_chemical_name_systematic
;
2-({1-[2-(Methylsulfanyl)phenyl]-1H-tetrazol-5-yl}sulfanyl)acetic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                74.7480(14)
_cell_angle_beta                 79.3090(14)
_cell_angle_gamma                86.286(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1500(3)
_cell_length_b                   8.3770(3)
_cell_length_c                   11.0890(5)
_cell_measurement_reflns_used    2086
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      19.80
_cell_measurement_theta_min      10.36
_cell_volume                     629.58(5)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_source         Fine-focus
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15888
_diffrn_reflns_theta_full        25.69
_diffrn_reflns_theta_max         25.69
_diffrn_reflns_theta_min         3.81
_exptl_absorpt_coefficient_mu    0.422
_exptl_absorpt_correction_T_max  0.8619
_exptl_absorpt_correction_T_min  0.8614
_exptl_absorpt_correction_type   cylinder
_exptl_absorpt_process_details   '(Dwiggins, 1975)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.296
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0968P)²+0.1021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.15
_reflns_number_gt                1879
_reflns_number_total             2335
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2571.cif
_cod_data_source_block           I
_cod_original_cell_volume        629.58(4)
_cod_database_code               2238028
_cod_database_fobs_code          2238028
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
S S1 0.12427(8) 0.32835(9) 0.14822(6) 0.0644(3) Uani d . 1
S S2 0.31586(12) 0.16473(8) 0.46904(6) 0.0744(3) Uani d . 1
O O1 0.3263(3) 0.0525(3) -0.07328(19) 0.0753(6) Uani d . 1
H H1 0.367(6) -0.039(5) -0.072(4) 0.113 Uiso d . 1
O O2 0.1581(4) -0.0338(3) 0.1185(2) 0.0973(8) Uani d . 1
N N1 0.5089(3) 0.2791(3) 0.0763(2) 0.0593(5) Uani d . 1
N N2 0.6701(3) 0.3173(3) 0.1112(2) 0.0621(5) Uani d . 1
N N3 0.6313(3) 0.3917(3) 0.2004(2) 0.0593(5) Uani d . 1
N N4 0.4384(2) 0.4047(2) 0.22640(17) 0.0490(4) Uani d . 1
C C1 0.2079(3) 0.0747(3) 0.0282(2) 0.0576(6) Uani d . 1
C C2 0.1398(3) 0.2518(3) 0.0096(2) 0.0546(5) Uani d . 1
H H2A 0.0153 0.2615 -0.0148 0.066 Uiso calc R 1
H H2B 0.2261 0.3207 -0.0597 0.066 Uiso calc R 1
C C3 0.3657(3) 0.3352(3) 0.1496(2) 0.0507(5) Uani d . 1
C C4 0.3483(3) 0.4803(3) 0.3259(2) 0.0497(5) Uani d . 1
C C5 0.3341(4) 0.6503(3) 0.2979(2) 0.0597(6) Uani d . 1
H H5 0.3723 0.7138 0.2153 0.072 Uiso calc R 1
C C6 0.2621(4) 0.7248(4) 0.3944(3) 0.0721(7) Uani d . 1
H H6 0.2489 0.8394 0.3774 0.087 Uiso calc R 1
C C7 0.2099(4) 0.6277(4) 0.5165(3) 0.0736(8) Uani d . 1
H H7 0.1645 0.6782 0.5817 0.088 Uiso calc R 1
C C8 0.2235(4) 0.4586(4) 0.5438(2) 0.0637(6) Uani d . 1
H H8 0.1866 0.396 0.6267 0.076 Uiso calc R 1
C C9 0.2925(3) 0.3800(3) 0.4476(2) 0.0539(5) Uani d . 1
C C10 0.2427(5) 0.0824(4) 0.6350(3) 0.0923(10) Uani d . 1
H H10A 0.3274 0.1185 0.68 0.138 Uiso calc R 1
H H10B 0.2456 -0.0363 0.6544 0.138 Uiso calc R 1
H H10C 0.1156 0.1204 0.6604 0.138 Uiso calc R 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 0 '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 0.006 '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
_geom_angle_publ_flag
C3 S1 C2 98.45(10) no
C9 S2 C10 104.17(14) no
C1 O1 H1 118(3) no
C3 N1 N2 105.52(19) no
N3 N2 N1 111.51(18) no
N2 N3 N4 106.22(18) no
C3 N4 N3 108.48(17) no
C3 N4 C4 131.62(18) no
N3 N4 C4 119.88(18) no
O2 C1 O1 123.2(2) no
O2 C1 C2 125.3(2) no
O1 C1 C2 111.4(2) no
C1 C2 S1 113.73(17) no
C1 C2 H2A 108.8 n
S1 C2 H2A 108.8 n
C1 C2 H2B 108.8 n
S1 C2 H2B 108.8 n
H2A C2 H2B 107.7 n
N1 C3 N4 108.27(19) no
N1 C3 S1 127.70(17) no
N4 C3 S1 124.01(16) no
C5 C4 C9 122.8(2) no
C5 C4 N4 118.2(2) no
C9 C4 N4 118.91(19) no
C4 C5 C6 118.8(2) no
C4 C5 H5 120.6 n
C6 C5 H5 120.6 n
C7 C6 C5 119.3(3) no
C7 C6 H6 120.3 n
C5 C6 H6 120.3 n
C8 C7 C6 121.6(2) no
C8 C7 H7 119.2 n
C6 C7 H7 119.2 n
C7 C8 C9 120.2(2) no
C7 C8 H8 119.9 n
C9 C8 H8 119.9 n
C4 C9 C8 117.2(2) no
C4 C9 S2 117.76(17) no
C8 C9 S2 125.01(19) no
S2 C10 H10A 109.5 n
S2 C10 H10B 109.5 n
H10A C10 H10B 109.5 n
S2 C10 H10C 109.5 n
H10A C10 H10C 109.5 n
H10B C10 H10C 109.5 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C3 1.734(2) no
S1 C2 1.798(2) no
S2 C9 1.757(3) no
S2 C10 1.778(3) no
O1 C1 1.324(3) no
O1 H1 0.80(4) no
O2 C1 1.177(3) no
N1 C3 1.327(3) no
N1 N2 1.364(3) no
N2 N3 1.282(3) no
N3 N4 1.359(3) no
N4 C3 1.341(3) no
N4 C4 1.444(3) no
C1 C2 1.504(3) no
C2 H2A 0.97 n
C2 H2B 0.97 n
C4 C5 1.376(3) no
C4 C9 1.391(3) no
C5 C6 1.381(4) no
C5 H5 0.93 n
C6 C7 1.380(4) no
C6 H6 0.93 n
C7 C8 1.369(4) no
C7 H7 0.93 n
C8 C9 1.395(3) no
C8 H8 0.93 n
C10 H10A 0.96 n
C10 H10B 0.96 n
C10 H10C 0.96 n
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 N1 2_655 0.81(4) 2.15(4) 2.952(4) 176(4)
O1 H1 N2 2_655 0.81(4) 2.51(4) 3.232(4) 149(4)
