#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/99/2239983.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_2239983
loop_
_publ_author_name
'Zhang, Yong-Le'
'Zhang, Chuang'
'Guo, Wei'
'Wang, Jing'
_publ_section_title
;
 Crystal structure of
 4-{[(1H-1,2,4-triazol-1-yl)methyl]sulfanyl}phenol
;
_journal_coeditor_code           DS2243
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1106
_journal_paper_doi               10.1107/S1600536814019965
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C9 H9 N3 O S'
_chemical_formula_moiety         'C9 H9 N3 O S'
_chemical_formula_sum            'C9 H9 N3 O S'
_chemical_formula_weight         207.25
_chemical_name_systematic
;
4-{[(1H-1,2,4-Triazol-1-yl)methyl]sulfanyl}phenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.010(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3975(10)
_cell_length_b                   10.0099(19)
_cell_length_c                   18.311(3)
_cell_measurement_reflns_used    1691
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.82
_cell_measurement_theta_min      2.32
_cell_volume                     989.2(3)
_computing_cell_refinement       'APEX2 (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4977
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.9431
_exptl_absorpt_correction_T_min  0.9217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       strip
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0323
_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)+(0.0294P)²+0.2664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                1453
_reflns_number_total             1755
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ds2243sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2239983
_cod_database_fobs_code          2239983
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
S S1 0.66005(10) 0.44273(5) 0.08502(3) 0.05715(18) Uani d . 1 1
O O1 1.2294(3) 0.31388(12) 0.35509(7) 0.0530(4) Uani d . 1 1
H H1 1.3233 0.3747 0.3671 0.080 Uiso calc R 1 1
N N1 0.8498(2) 0.20284(13) 0.04543(7) 0.0369(3) Uani d . 1 1
N N2 0.6462(2) 0.12317(15) 0.04545(8) 0.0450(4) Uani d . 1 1
N N3 0.9755(3) 0.01570(15) 0.09366(8) 0.0475(4) Uani d . 1 1
C C1 0.7326(3) 0.01291(19) 0.07461(9) 0.0461(4) Uani d . 1 1
H H1A 0.6339 -0.0620 0.0817 0.055 Uiso calc R 1 1
C C2 1.0418(3) 0.13729(18) 0.07465(9) 0.0440(4) Uani d . 1 1
H H2 1.2004 0.1724 0.0808 0.053 Uiso calc R 1 1
C C3 0.8344(3) 0.34022(18) 0.02238(10) 0.0483(5) Uani d . 1 1
H H3A 0.7561 0.3442 -0.0257 0.058 Uiso calc R 1 1
H H3B 1.0006 0.3762 0.0185 0.058 Uiso calc R 1 1
C C4 0.8297(3) 0.40921(17) 0.16692(9) 0.0436(4) Uani d . 1 1
C C5 0.7646(3) 0.30194(19) 0.21040(10) 0.0487(5) Uani d . 1 1
H H5 0.6281 0.2499 0.1974 0.058 Uiso calc R 1 1
C C6 0.9001(4) 0.27158(18) 0.27266(10) 0.0487(5) Uani d . 1 1
H H6 0.8549 0.1990 0.3012 0.058 Uiso calc R 1 1
C C7 1.1036(3) 0.34846(16) 0.29307(9) 0.0403(4) Uani d . 1 1
C C8 1.1682(3) 0.45690(18) 0.25025(10) 0.0458(4) Uani d . 1 1
H H8 1.3035 0.5096 0.2636 0.055 Uiso calc R 1 1
C C9 1.0315(4) 0.48657(18) 0.18780(10) 0.0477(5) Uani d . 1 1
H H9 1.0757 0.5595 0.1594 0.057 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
S1 0.0629(3) 0.0550(3) 0.0531(3) 0.0208(2) -0.0116(2) -0.0047(2)
O1 0.0666(9) 0.0444(7) 0.0476(7) -0.0068(6) -0.0120(6) 0.0013(6)
N1 0.0317(7) 0.0419(8) 0.0370(8) -0.0003(6) -0.0013(6) -0.0019(6)
N2 0.0338(8) 0.0530(9) 0.0481(9) -0.0058(7) -0.0062(6) -0.0003(7)
N3 0.0478(9) 0.0500(9) 0.0443(9) 0.0054(7) -0.0067(7) 0.0001(7)
C1 0.0470(11) 0.0484(11) 0.0427(10) -0.0062(8) -0.0011(8) 0.0010(8)
C2 0.0309(9) 0.0542(12) 0.0466(10) 0.0011(8) -0.0041(7) -0.0057(9)
C3 0.0553(11) 0.0473(11) 0.0424(10) 0.0003(9) -0.0001(8) 0.0043(8)
C4 0.0471(10) 0.0402(10) 0.0434(10) 0.0082(8) -0.0015(8) -0.0072(8)
C5 0.0476(10) 0.0489(11) 0.0496(11) -0.0088(8) -0.0010(8) -0.0080(9)
C6 0.0609(12) 0.0402(10) 0.0449(10) -0.0115(9) 0.0023(9) 0.0005(8)
C7 0.0473(10) 0.0369(9) 0.0366(9) 0.0017(8) 0.0012(7) -0.0057(7)
C8 0.0463(10) 0.0414(10) 0.0495(11) -0.0077(8) -0.0002(8) -0.0027(8)
C9 0.0583(11) 0.0376(10) 0.0473(11) -0.0001(8) 0.0044(9) 0.0021(8)
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
C4 S1 C3 99.29(8)
C7 O1 H1 109.5
C2 N1 N2 109.56(14)
C2 N1 C3 128.98(15)
N2 N1 C3 121.22(14)
C1 N2 N1 102.31(13)
C2 N3 C1 102.59(15)
N2 C1 N3 115.15(16)
N2 C1 H1A 122.4
N3 C1 H1A 122.4
N3 C2 N1 110.40(15)
N3 C2 H2 124.8
N1 C2 H2 124.8
N1 C3 S1 112.49(12)
N1 C3 H3A 109.1
S1 C3 H3A 109.1
N1 C3 H3B 109.1
S1 C3 H3B 109.1
H3A C3 H3B 107.8
C9 C4 C5 118.74(17)
C9 C4 S1 121.27(14)
C5 C4 S1 119.97(14)
C6 C5 C4 120.68(17)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C7 120.46(17)
C5 C6 H6 119.8
C7 C6 H6 119.8
O1 C7 C6 117.77(15)
O1 C7 C8 123.04(15)
C6 C7 C8 119.19(16)
C9 C8 C7 120.00(17)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C4 120.93(17)
C8 C9 H9 119.5
C4 C9 H9 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.7753(18)
S1 C3 1.8146(18)
O1 C7 1.358(2)
O1 H1 0.8200
N1 C2 1.331(2)
N1 N2 1.3578(18)
N1 C3 1.440(2)
N2 C1 1.308(2)
N3 C2 1.317(2)
N3 C1 1.351(2)
C1 H1A 0.9300
C2 H2 0.9300
C3 H3A 0.9700
C3 H3B 0.9700
C4 C9 1.385(3)
C4 C5 1.386(3)
C5 C6 1.378(3)
C5 H5 0.9300
C6 C7 1.387(2)
C6 H6 0.9300
C7 C8 1.387(2)
C8 C9 1.382(2)
C8 H8 0.9300
C9 H9 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
O1 H1 N3 2_755 0.82 1.91 2.7290(19) 173.2
C2 H2 N2 1_655 0.93 2.55 3.318(2) 140.1
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
C2 N1 N2 C1 -0.58(18)
C3 N1 N2 C1 -175.34(14)
N1 N2 C1 N3 0.3(2)
C2 N3 C1 N2 0.1(2)
C1 N3 C2 N1 -0.45(19)
N2 N1 C2 N3 0.68(19)
C3 N1 C2 N3 174.91(15)
C2 N1 C3 S1 -105.58(18)
N2 N1 C3 S1 68.07(18)
C4 S1 C3 N1 55.54(14)
C3 S1 C4 C9 89.51(16)
C3 S1 C4 C5 -88.92(16)
C9 C4 C5 C6 -0.9(3)
S1 C4 C5 C6 177.54(14)
C4 C5 C6 C7 0.3(3)
C5 C6 C7 O1 179.81(16)
C5 C6 C7 C8 0.4(3)
O1 C7 C8 C9 -179.87(16)
C6 C7 C8 C9 -0.5(3)
C7 C8 C9 C4 -0.1(3)
C5 C4 C9 C8 0.8(3)
S1 C4 C9 C8 -177.62(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086948
