#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240339.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_7240339
loop_
_publ_author_name
'Akhmetova, Vnira R.'
'Akhmadiev, Nail S.'
'Abdullin, Marat F.'
'Dzhemileva, Lilya U.'
'D'yakonov, Vladimir A.'
_publ_section_title
;
 Synthesis of new N,N′-Pd(Pt) complexes based on sulfanyl
 pyrazoles, and investigation of their in vitro anticancer activity
;
_journal_issue                   26
_journal_name_full               'RSC Advances'
_journal_page_first              15116
_journal_page_last               15123
_journal_paper_doi               10.1039/C9RA09783J
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C12 H14 N2 O S'
_chemical_formula_sum            'C12 H14 N2 O S'
_chemical_formula_weight         234.31
_chemical_melting_point          459
_chemical_name_systematic
4-{[(3,5-dimethyl-1H-pyrazol-4-yl)methyl]sulfanyl}phenol
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-19 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.914(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.1997(11)
_cell_length_b                   7.7319(4)
_cell_length_c                   16.5888(10)
_cell_measurement_reflns_used    1732
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7030
_cell_measurement_theta_min      2.4940
_cell_volume                     2449.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -40.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.4011   77.0000   60.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2605   77.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega   47.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2605   77.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   -6.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2605   77.0000 -180.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0008367000
_diffrn_orient_matrix_UB_12      0.0802966000
_diffrn_orient_matrix_UB_13      -0.0208047000
_diffrn_orient_matrix_UB_21      0.0027556000
_diffrn_orient_matrix_UB_22      0.0443766000
_diffrn_orient_matrix_UB_23      0.0375955000
_diffrn_orient_matrix_UB_31      0.0370242000
_diffrn_orient_matrix_UB_32      -0.0015362000
_diffrn_orient_matrix_UB_33      0.0011444000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5838
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.139
_diffrn_reflns_theta_min         2.133
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'Agilent Xcalibur'
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       plank
_exptl_crystal_F_000             992.0
_exptl_crystal_recrystallization_method 'Acetone: Methanol'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0630P)²+0.8711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2095
_reflns_number_total             2802
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra09783j2.cif
_cod_data_source_block           ngm-298
_cod_depositor_comments          'Adding full bibliography for 7240339.cif.'
_cod_original_sg_symbol_Hall     '-C 2yn'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7240339
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), N2(H2), C11(H11), C14(H14), C10(H10)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C15(H15A,H15B,H15C)
;
loop_
_space_group_symop_operation_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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S8 S 0.07004(3) 0.55074(6) 0.10445(3) 0.0581(2) Uani 1 1 d . . . . .
O16 O 0.24490(7) 0.84994(18) 0.38518(8) 0.0458(3) Uani 1 1 d . . . . .
N1 N 0.16101(9) 1.0348(2) -0.00754(10) 0.0513(4) Uani 1 1 d . . . . .
C13 C 0.22730(9) 0.7835(2) 0.24553(11) 0.0416(4) Uani 1 1 d . . . . .
H13 H 0.269250 0.838621 0.238218 0.050 Uiso 1 1 calc R . . . .
N2 N 0.14719(8) 1.1127(2) 0.06199(10) 0.0463(4) Uani 1 1 d . . . . .
H2 H 0.167573 1.205495 0.080713 0.056 Uiso 1 1 calc R . . . .
C11 C 0.14305(10) 0.6882(3) 0.33289(12) 0.0467(5) Uani 1 1 d . . . . .
H11 H 0.128765 0.677450 0.384549 0.056 Uiso 1 1 calc R . . . .
C12 C 0.20455(9) 0.7747(2) 0.32197(11) 0.0387(4) Uani 1 1 d . . . . .
C9 C 0.12403(10) 0.6306(2) 0.18953(12) 0.0430(4) Uani 1 1 d . . . . .
C14 C 0.18748(10) 0.7103(2) 0.18009(11) 0.0434(4) Uani 1 1 d . . . . .
H14 H 0.203439 0.714424 0.129062 0.052 Uiso 1 1 calc R . . . .
C3 C 0.09777(10) 1.0281(2) 0.09855(11) 0.0416(4) Uani 1 1 d . . . . .
C5 C 0.11828(10) 0.8979(3) -0.01531(12) 0.0474(5) Uani 1 1 d . . . . .
C4 C 0.07741(9) 0.8890(2) 0.04954(11) 0.0402(4) Uani 1 1 d . . . . .
C7 C 0.02692(10) 0.7518(3) 0.06689(13) 0.0507(5) Uani 1 1 d . . . . .
H7A H -0.003322 0.726851 0.017774 0.061 Uiso 1 1 calc R . . . .
H7B H -0.002263 0.794331 0.106987 0.061 Uiso 1 1 calc R . . . .
C10 C 0.10297(10) 0.6181(3) 0.26709(13) 0.0504(5) Uani 1 1 d . . . . .
H10 H 0.061345 0.561832 0.274697 0.061 Uiso 1 1 calc R . . . .
C6 C 0.07680(13) 1.0859(3) 0.17827(14) 0.0629(6) Uani 1 1 d . . . . .
H6A H 0.105842 1.030137 0.221162 0.094 Uiso 1 1 calc GR . . . .
H6B H 0.028708 1.055905 0.181944 0.094 Uiso 1 1 calc GR . . . .
H6C H 0.082324 1.209016 0.183053 0.094 Uiso 1 1 calc GR . . . .
C15 C 0.12027(15) 0.7765(4) -0.08548(14) 0.0804(8) Uani 1 1 d . . . . .
H15A H 0.142517 0.832348 -0.127706 0.121 Uiso 1 1 calc GR . . . .
H15B H 0.073363 0.744575 -0.105640 0.121 Uiso 1 1 calc GR . . . .
H15C H 0.146200 0.674655 -0.068017 0.121 Uiso 1 1 calc GR . . . .
H16 H 0.2205(13) 0.884(4) 0.4266(15) 0.083(8) Uiso 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S8 C7 100.42(9) . . ?
C5 N1 N2 105.22(15) . . ?
C14 C13 C12 119.84(17) . . ?
C3 N2 N1 112.16(16) . . ?
C10 C11 C12 119.97(17) . . ?
O16 C12 C13 118.28(17) . . ?
O16 C12 C11 121.89(16) . . ?
C13 C12 C11 119.82(17) . . ?
C14 C9 S8 120.82(15) . . ?
C14 C9 C10 118.49(17) . . ?
C10 C9 S8 120.67(15) . . ?
C13 C14 C9 120.91(17) . . ?
N2 C3 C4 106.44(17) . . ?
N2 C3 C6 121.40(18) . . ?
C4 C3 C6 132.12(18) . . ?
N1 C5 C4 110.64(17) . . ?
N1 C5 C15 120.41(19) . . ?
C4 C5 C15 128.9(2) . . ?
C3 C4 C5 105.54(17) . . ?
C3 C4 C7 126.39(18) . . ?
C5 C4 C7 127.88(18) . . ?
C4 C7 S8 112.91(13) . . ?
C11 C10 C9 120.85(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S8 C9 1.7737(19) . ?
S8 C7 1.840(2) . ?
O16 C12 1.368(2) . ?
N1 N2 1.352(2) . ?
N1 C5 1.337(3) . ?
C13 C12 1.385(2) . ?
C13 C14 1.383(3) . ?
N2 C3 1.347(2) . ?
C11 C12 1.385(3) . ?
C11 C10 1.380(3) . ?
C9 C14 1.388(3) . ?
C9 C10 1.391(3) . ?
C3 C4 1.380(3) . ?
C3 C6 1.490(3) . ?
C5 C4 1.397(3) . ?
C5 C15 1.499(3) . ?
C4 C7 1.485(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341250
