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#$Date: 2025-07-06 18:38:46 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300785 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/85/7718557.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_7718557
loop_
_publ_author_name
'Skvortsova, Sofia V.'
'Verkhov, Fyodor K.'
'Nikolaenkova, Elena B.'
'Rakhmanova, Marianna I.'
'Kokina, Tatiana E.'
'Sukhikh, Taisiya S.'
'Shekhovtsov, Nikita A.'
'Bushuev, Mark B.'
_publ_section_title
;
 Interplay of the Cu⋯Cu distance and coordination geometry as a
 factor affecting the quantum efficiency in dimeric copper(I) halide
 complexes with derivatives of 4-pyrazolylpyrimidine-2-thiol.
;
_journal_issue                   22
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9000
_journal_page_last               9015
_journal_paper_doi               10.1039/d5dt00498e
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C17 H18 N4 S'
_chemical_formula_sum            'C17 H18 N4 S'
_chemical_formula_weight         310.41
_chemical_name_systematic
2-(benzylthio)-4-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylpyrimidine
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-02-17 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.397(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0358(8)
_cell_length_b                   6.7859(6)
_cell_length_c                   11.4683(7)
_cell_measurement_reflns_used    2742
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      74.60
_cell_measurement_theta_min      3.92
_cell_volume                     844.73(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8763
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.591
_diffrn_reflns_theta_min         3.919
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.705
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0987 before and 0.0679 after correction.
The Ratio of minimum to maximum transmission is 0.8042.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0385
_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)+(0.0465P)²+0.1640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1495
_reflns_number_total             1864
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt00498e2.cif
_cod_data_source_block           l128
_cod_depositor_comments
'Adding full bibliography for 7718557--7718562.cif.'
_cod_database_code               7718557
_shelx_shelxl_version_number     2019/3
_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.
;
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.862
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H14A(0.5) H14B(0.5) H14C(0.5) H15A(0.5) H15B(0.5) H15C(0.5)
 H17A(0.5) H17B(0.5) H17C(0.5)
3.a Idealised Me refined as rotating group:
 C141(H14A,H14B,H14C), C151(H15A,H15B,H15C), C171(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
S1 S 0.25499(5) 0.750000 0.54229(5) 0.03082(18) Uani 1 2 d S T P . .
N1 N 0.50153(18) 0.750000 0.58008(16) 0.0279(4) Uani 1 2 d S T P . .
N2 N 0.39062(18) 0.750000 0.37993(15) 0.0269(4) Uani 1 2 d S T P . .
N3 N 0.49198(17) 0.750000 0.21857(15) 0.0258(4) Uani 1 2 d S T P . .
N4 N 0.60158(18) 0.750000 0.17656(17) 0.0299(4) Uani 1 2 d S T P . .
C11 C 0.3997(2) 0.750000 0.49805(18) 0.0261(5) Uani 1 2 d S T P . .
C12 C 0.4979(2) 0.750000 0.34180(18) 0.0247(5) Uani 1 2 d S T P . .
C13 C 0.6113(2) 0.750000 0.41814(19) 0.0276(5) Uani 1 2 d S T P . .
H13 H 0.684(3) 0.750000 0.391(2) 0.033(7) Uiso 1 2 d S . P . .
C14 C 0.6088(2) 0.750000 0.53819(19) 0.0272(5) Uani 1 2 d S T P . .
C15 C 0.5686(2) 0.750000 0.05975(19) 0.0302(5) Uani 1 2 d S T P . .
C16 C 0.4397(2) 0.750000 0.0253(2) 0.0324(5) Uani 1 2 d S T P . .
H16 H 0.394(3) 0.750000 -0.050(3) 0.044(8) Uiso 1 2 d S . P . .
C17 C 0.3915(2) 0.750000 0.12717(19) 0.0276(5) Uani 1 2 d S T P . .
C111 C 0.3017(2) 0.750000 0.70288(19) 0.0311(5) Uani 1 2 d S T P . .
H111 H 0.3544(19) 0.869(3) 0.7278(18) 0.048(6) Uiso 1 1 d . . . . .
C112 C 0.1873(2) 0.750000 0.75845(18) 0.0304(5) Uani 1 2 d S T P . .
C113 C 0.13511(18) 0.5746(3) 0.78505(17) 0.0418(5) Uani 1 1 d . . . . .
H113 H 0.1685(19) 0.447(3) 0.7672(18) 0.049(6) Uiso 1 1 d . . . . .
C114 C 0.0315(2) 0.5757(4) 0.83904(18) 0.0525(6) Uani 1 1 d . . . . .
H114 H -0.003(2) 0.445(4) 0.856(2) 0.062(7) Uiso 1 1 d . . . . .
C115 C -0.0199(3) 0.750000 0.8652(2) 0.0516(8) Uani 1 2 d S T P . .
H115 H -0.094(3) 0.750000 0.904(3) 0.056(9) Uiso 1 2 d S . P . .
C141 C 0.7248(2) 0.750000 0.6288(2) 0.0342(5) Uani 1 2 d S T P . .
H14A H 0.709703 0.814526 0.701229 0.051 Uiso 0.5 1 calc R U P A -1
H14B H 0.789243 0.821571 0.597622 0.051 Uiso 0.5 1 calc R U P A -1
H14C H 0.751531 0.613903 0.646744 0.051 Uiso 0.5 1 calc R U P A -1
C151 C 0.6642(3) 0.750000 -0.0180(2) 0.0383(6) Uani 1 2 d S T P . .
H15A H 0.627945 0.800364 -0.096655 0.057 Uiso 0.5 1 calc R U P B -1
H15B H 0.693880 0.615265 -0.025353 0.057 Uiso 0.5 1 calc R U P B -1
H15C H 0.733240 0.834370 0.017210 0.057 Uiso 0.5 1 calc R U P B -1
C171 C 0.2594(2) 0.750000 0.1398(2) 0.0366(6) Uani 1 2 d S T P . .
H17A H 0.207188 0.752836 0.061042 0.055 Uiso 0.5 1 calc R U P C -1
H17B H 0.242529 0.866473 0.184791 0.055 Uiso 0.5 1 calc R U P C -1
H17C H 0.241689 0.630692 0.181850 0.055 Uiso 0.5 1 calc R U P C -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C11 S1 C111 100.69(11) . . ?
C11 N1 C14 115.48(18) . . ?
C12 N2 C11 115.00(19) . . ?
N4 N3 C12 117.85(18) . . ?
N4 N3 C17 111.65(16) . . ?
C17 N3 C12 130.51(19) . . ?
C15 N4 N3 104.77(18) . . ?
N1 C11 S1 119.41(15) . . ?
N1 C11 N2 127.9(2) . . ?
N2 C11 S1 112.66(17) . . ?
N2 C12 N3 116.58(19) . . ?
N2 C12 C13 122.96(19) . . ?
C13 C12 N3 120.46(19) . . ?
C12 C13 H13 122.2(17) . . ?
C14 C13 C12 116.7(2) . . ?
C14 C13 H13 121.1(17) . . ?
N1 C14 C13 121.9(2) . . ?
N1 C14 C141 116.54(19) . . ?
C13 C14 C141 121.6(2) . . ?
N4 C15 C16 111.33(19) . . ?
N4 C15 C151 120.5(2) . . ?
C16 C15 C151 128.2(2) . . ?
C15 C16 H16 128.8(18) . . ?
C17 C16 C15 106.8(2) . . ?
C17 C16 H16 124.4(18) . . ?
N3 C17 C171 126.25(19) . . ?
C16 C17 N3 105.4(2) . . ?
C16 C17 C171 128.3(2) . . ?
S1 C111 H111 109.3(12) . . ?
S1 C111 H111 109.3(12) . 4_575 ?
H111 C111 H111 107(2) . 4_575 ?
C112 C111 S1 108.69(16) . . ?
C112 C111 H111 111.3(11) . . ?
C112 C111 H111 111.3(12) . 4_575 ?
C113 C112 C111 120.42(11) 4_575 . ?
C113 C112 C111 120.42(11) . . ?
C113 C112 C113 119.1(2) . 4_575 ?
C112 C113 H113 122.0(12) . . ?
C112 C113 C114 120.1(2) . . ?
C114 C113 H113 117.8(12) . . ?
C113 C114 H114 117.2(14) . . ?
C115 C114 C113 120.4(2) . . ?
C115 C114 H114 122.3(14) . . ?
C114 C115 C114 119.7(3) . 4_575 ?
C114 C115 H115 120.15(13) . . ?
C114 C115 H115 120.16(13) 4_575 . ?
C14 C141 H14A 109.5 . . ?
C14 C141 H14B 109.5 . . ?
C14 C141 H14C 109.5 . . ?
H14A C141 H14B 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
C15 C151 H15A 109.5 . . ?
C15 C151 H15B 109.5 . . ?
C15 C151 H15C 109.5 . . ?
H15A C151 H15B 109.5 . . ?
H15A C151 H15C 109.5 . . ?
H15B C151 H15C 109.5 . . ?
C17 C171 H17A 109.5 . . ?
C17 C171 H17B 109.5 . . ?
C17 C171 H17C 109.5 . . ?
H17A C171 H17B 109.5 . . ?
H17A C171 H17C 109.5 . . ?
H17B C171 H17C 109.5 . . ?
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
S1 C11 1.761(2) . ?
S1 C111 1.821(2) . ?
N1 C11 1.329(3) . ?
N1 C14 1.355(3) . ?
N2 C11 1.340(3) . ?
N2 C12 1.334(3) . ?
N3 N4 1.380(2) . ?
N3 C12 1.403(3) . ?
N3 C17 1.381(3) . ?
N4 C15 1.323(3) . ?
C12 C13 1.391(3) . ?
C13 H13 0.91(3) . ?
C13 C14 1.382(3) . ?
C14 C141 1.496(3) . ?
C15 C16 1.406(4) . ?
C15 C151 1.499(3) . ?
C16 H16 0.92(3) . ?
C16 C17 1.368(3) . ?
C17 C171 1.491(3) . ?
C111 H111 1.01(2) 4_575 ?
C111 H111 1.01(2) . ?
C111 C112 1.513(3) . ?
C112 C113 1.380(2) . ?
C112 C113 1.380(2) 4_575 ?
C113 H113 0.98(2) . ?
C113 C114 1.396(2) . ?
C114 H114 1.00(3) . ?
C114 C115 1.368(3) . ?
C115 H115 1.00(3) . ?
C141 H14A 0.9800 . ?
C141 H14B 0.9800 . ?
C141 H14C 0.9800 . ?
C151 H15A 0.9800 . ?
C151 H15B 0.9800 . ?
C151 H15C 0.9800 . ?
C171 H17A 0.9800 . ?
C171 H17B 0.9800 . ?
C171 H17C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C111 C112 C113 90.56(19) . . . . ?
S1 C111 C112 C113 -90.56(19) . . . 4_575 ?
N2 C12 C13 C14 0.000(0) . . . . ?
N3 N4 C15 C16 0.000(0) . . . . ?
N3 N4 C15 C151 180.000(0) . . . . ?
N3 C12 C13 C14 180.000(0) . . . . ?
N4 N3 C12 N2 180.000(0) . . . . ?
N4 N3 C12 C13 0.000(0) . . . . ?
N4 N3 C17 C16 0.000(0) . . . . ?
N4 N3 C17 C171 180.000(0) . . . . ?
N4 C15 C16 C17 0.000(0) . . . . ?
C11 S1 C111 C112 180.000(0) . . . . ?
C11 N1 C14 C13 0.000(1) . . . . ?
C11 N1 C14 C141 180.000(0) . . . . ?
C11 N2 C12 N3 180.000(0) . . . . ?
C11 N2 C12 C13 0.000(0) . . . . ?
C12 N2 C11 S1 180.000(0) . . . . ?
C12 N2 C11 N1 0.000(1) . . . . ?
C12 N3 N4 C15 180.000(0) . . . . ?
C12 N3 C17 C16 180.000(0) . . . . ?
C12 N3 C17 C171 0.000(0) . . . . ?
C12 C13 C14 N1 0.000(1) . . . . ?
C12 C13 C14 C141 180.000(0) . . . . ?
C14 N1 C11 S1 180.000(0) . . . . ?
C14 N1 C11 N2 0.000(1) . . . . ?
C15 C16 C17 N3 0.000(0) . . . . ?
C15 C16 C17 C171 180.000(0) . . . . ?
C17 N3 N4 C15 0.000(0) . . . . ?
C17 N3 C12 N2 0.000(0) . . . . ?
C17 N3 C12 C13 180.000(0) . . . . ?
C111 S1 C11 N1 0.000(0) . . . . ?
C111 S1 C11 N2 180.000(0) . . . . ?
C111 C112 C113 C114 178.4(2) . . . . ?
C112 C113 C114 C115 0.5(3) . . . . ?
C113 C112 C113 C114 -0.5(4) 4_575 . . . ?
C113 C114 C115 C114 -0.5(4) . . . 4_575 ?
C151 C15 C16 C17 180.0 . . . . ?
