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#$Date: 2023-06-02 11:58:18 +0300 (Fri, 02 Jun 2023) $
#$Revision: 284151 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107295.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_8107295
loop_
_publ_author_name
'Al-Wahaibi, Lamya H.'
'Abdelbaky, Mohammed S. M.'
'Garcia-Granda, Santiago'
'Tiekink, Edward R. T.'
'El-Emam, Ali A.'
_publ_section_title
;
 Crystal structure of
 3-(adamantan-1-yl)-4-methyl-5-{[(4-nitrophenyl)methyl]sulfanyl}-4H-1,2,4-triazole,
 C20H24N4O2S
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1067
_journal_page_last               1070
_journal_paper_doi               10.1515/ncrs-2022-0392
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C20 H24 N4 O2 S'
_chemical_formula_sum            'C20 H24 N4 O2 S'
_chemical_formula_weight         384.49
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 99.682(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.5901(10)
_cell_length_b                   6.4383(4)
_cell_length_c                   20.0600(10)
_cell_measurement_reflns_used    1594
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.4530
_cell_measurement_theta_min      3.1260
_cell_volume                     3639.9(3)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT [2]'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16466
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         75.805
_diffrn_reflns_theta_min         3.136
_exptl_absorpt_coefficient_mu    1.777
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro [1]
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0557
_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)+(0.0639P)²+0.2426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1514
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2330
_reflns_number_total             3726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0392_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8107295
_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.
;
_shelx_estimated_absorpt_t_min   0.740
_shelx_estimated_absorpt_t_max   0.901
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
S1 S 0.42766(3) 0.30733(16) 0.68614(4) 0.0418(3) Uani 1 1 d . . . . .
O1 O 0.53920(9) 0.7788(5) 0.98621(14) 0.0587(8) Uani 1 1 d . . . . .
O2 O 0.52822(10) 1.0658(5) 0.93034(14) 0.0590(8) Uani 1 1 d . . . . .
N1 N 0.33771(10) -0.0530(5) 0.57618(13) 0.0421(7) Uani 1 1 d . . . . .
N2 N 0.36515(11) 0.0031(5) 0.63718(14) 0.0465(8) Uani 1 1 d . . . . .
N3 N 0.37213(8) 0.2435(4) 0.56105(13) 0.0336(6) Uani 1 1 d . . . . .
N4 N 0.52057(9) 0.8800(5) 0.93738(15) 0.0422(7) Uani 1 1 d . . . . .
C1 C 0.34254(10) 0.0918(5) 0.53107(15) 0.0315(7) Uani 1 1 d . . . . .
C2 C 0.38512(10) 0.1800(6) 0.62679(15) 0.0360(8) Uani 1 1 d . . . . .
C3 C 0.32083(10) 0.0738(5) 0.45725(14) 0.0271(6) Uani 1 1 d . . . . .
C4 C 0.29333(10) 0.2690(5) 0.42840(15) 0.0293(7) Uani 1 1 d . . . . .
H4A H 0.268038 0.300134 0.455099 0.035 Uiso 1 1 calc R U . . .
H4B H 0.315172 0.389336 0.432052 0.035 Uiso 1 1 calc R U . . .
C5 C 0.27119(10) 0.2354(5) 0.35415(15) 0.0314(7) Uani 1 1 d . . . . .
H5 H 0.253704 0.363681 0.336292 0.038 Uiso 1 1 calc R U . . .
C6 C 0.31046(10) 0.1901(5) 0.31286(15) 0.0323(7) Uani 1 1 d . . . . .
H6A H 0.332693 0.309005 0.316063 0.039 Uiso 1 1 calc R U . . .
H6B H 0.296430 0.170365 0.264695 0.039 Uiso 1 1 calc R U . . .
C7 C 0.33727(10) -0.0068(5) 0.34022(15) 0.0310(7) Uani 1 1 d . . . . .
H7 H 0.362769 -0.036683 0.313019 0.037 Uiso 1 1 calc R U . . .
C8 C 0.35982(10) 0.0247(5) 0.41457(15) 0.0319(7) Uani 1 1 d . . . . .
H8A H 0.382847 0.140705 0.418213 0.038 Uiso 1 1 calc R U . . .
H8B H 0.377117 -0.102573 0.431997 0.038 Uiso 1 1 calc R U . . .
C9 C 0.30278(10) -0.1896(5) 0.33431(15) 0.0335(7) Uani 1 1 d . . . . .
H9A H 0.319950 -0.317638 0.351308 0.040 Uiso 1 1 calc R U . . .
H9B H 0.288646 -0.211691 0.286306 0.040 Uiso 1 1 calc R U . . .
C10 C 0.28578(10) -0.1110(5) 0.44985(15) 0.0319(7) Uani 1 1 d . . . . .
H10A H 0.302774 -0.238652 0.467633 0.038 Uiso 1 1 calc R U . . .
H10B H 0.260439 -0.083809 0.476812 0.038 Uiso 1 1 calc R U . . .
C11 C 0.26358(10) -0.1440(5) 0.37571(15) 0.0322(7) Uani 1 1 d . . . . .
H11 H 0.241077 -0.263907 0.372130 0.039 Uiso 1 1 calc R U . . .
C12 C 0.23666(10) 0.0526(5) 0.34851(16) 0.0338(7) Uani 1 1 d . . . . .
H12A H 0.221975 0.031871 0.300654 0.041 Uiso 1 1 calc R U . . .
H12B H 0.211094 0.082046 0.374889 0.041 Uiso 1 1 calc R U . . .
C13 C 0.38872(12) 0.4329(6) 0.53311(18) 0.0436(9) Uani 1 1 d . . . . .
H13A H 0.418684 0.476551 0.560731 0.065 Uiso 1 1 calc R U . . .
H13B H 0.364956 0.542582 0.533101 0.065 Uiso 1 1 calc R U . . .
H13C H 0.393692 0.407107 0.486661 0.065 Uiso 1 1 calc R U . . .
C14 C 0.39039(10) 0.4716(6) 0.73011(17) 0.0387(8) Uani 1 1 d . . . . .
H14A H 0.372873 0.574265 0.698623 0.046 Uiso 1 1 calc R U . . .
H14B H 0.367201 0.386281 0.749522 0.046 Uiso 1 1 calc R U . . .
C15 C 0.42390(10) 0.5799(6) 0.78545(16) 0.0347(7) Uani 1 1 d . . . . .
C16 C 0.44075(11) 0.4790(6) 0.84613(16) 0.0364(8) Uani 1 1 d . . . . .
H16 H 0.430261 0.342067 0.853324 0.044 Uiso 1 1 calc R U . . .
C17 C 0.47270(10) 0.5762(6) 0.89623(16) 0.0380(8) Uani 1 1 d . . . . .
H17 H 0.484404 0.507332 0.937555 0.046 Uiso 1 1 calc R U . . .
C18 C 0.48700(10) 0.7756(5) 0.88441(16) 0.0330(7) Uani 1 1 d . . . . .
C19 C 0.47070(11) 0.8812(6) 0.82517(17) 0.0378(8) Uani 1 1 d . . . . .
H19 H 0.480956 1.018943 0.818596 0.045 Uiso 1 1 calc R U . . .
C20 C 0.43898(10) 0.7814(6) 0.77548(17) 0.0389(8) Uani 1 1 d . . . . .
H20 H 0.427447 0.851266 0.734265 0.047 Uiso 1 1 calc R U . . .
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'
O O 0.0492 0.0322 '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
C2 S1 C14 101.77(14) . .
C1 N1 N2 108.2(3) . .
C2 N2 N1 106.5(3) . .
C1 N3 C2 105.0(3) . .
C1 N3 C13 130.4(3) . .
C2 N3 C13 124.6(3) . .
O1 N4 O2 123.3(3) . .
O1 N4 C18 118.7(3) . .
O2 N4 C18 118.0(3) . .
N1 C1 N3 109.4(3) . .
N1 C1 C3 122.9(3) . .
N3 C1 C3 127.6(3) . .
N2 C2 N3 111.0(3) . .
N2 C2 S1 124.8(2) . .
N3 C2 S1 123.9(3) . .
C1 C3 C4 113.9(3) . .
C1 C3 C10 107.8(2) . .
C4 C3 C10 108.0(2) . .
C1 C3 C8 110.0(2) . .
C4 C3 C8 109.1(2) . .
C10 C3 C8 107.8(2) . .
C5 C4 C3 110.5(2) . .
C5 C4 H4A 109.5 . .
C3 C4 H4A 109.5 . .
C5 C4 H4B 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 108.1 . .
C12 C5 C6 109.7(3) . .
C12 C5 C4 109.7(2) . .
C6 C5 C4 109.4(2) . .
C12 C5 H5 109.4 . .
C6 C5 H5 109.4 . .
C4 C5 H5 109.4 . .
C5 C6 C7 109.4(2) . .
C5 C6 H6A 109.8 . .
C7 C6 H6A 109.8 . .
C5 C6 H6B 109.8 . .
C7 C6 H6B 109.8 . .
H6A C6 H6B 108.3 . .
C9 C7 C8 109.7(2) . .
C9 C7 C6 109.4(2) . .
C8 C7 C6 109.9(3) . .
C9 C7 H7 109.3 . .
C8 C7 H7 109.3 . .
C6 C7 H7 109.3 . .
C7 C8 C3 109.9(2) . .
C7 C8 H8A 109.7 . .
C3 C8 H8A 109.7 . .
C7 C8 H8B 109.7 . .
C3 C8 H8B 109.7 . .
H8A C8 H8B 108.2 . .
C7 C9 C11 109.4(3) . .
C7 C9 H9A 109.8 . .
C11 C9 H9A 109.8 . .
C7 C9 H9B 109.8 . .
C11 C9 H9B 109.8 . .
H9A C9 H9B 108.2 . .
C11 C10 C3 110.9(2) . .
C11 C10 H10A 109.5 . .
C3 C10 H10A 109.5 . .
C11 C10 H10B 109.5 . .
C3 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
C10 C11 C9 109.4(2) . .
C10 C11 C12 109.4(3) . .
C9 C11 C12 109.6(3) . .
C10 C11 H11 109.5 . .
C9 C11 H11 109.5 . .
C12 C11 H11 109.5 . .
C5 C12 C11 109.3(2) . .
C5 C12 H12A 109.8 . .
C11 C12 H12A 109.8 . .
C5 C12 H12B 109.8 . .
C11 C12 H12B 109.8 . .
H12A C12 H12B 108.3 . .
N3 C13 H13A 109.5 . .
N3 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
N3 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 S1 105.8(2) . .
C15 C14 H14A 110.6 . .
S1 C14 H14A 110.6 . .
C15 C14 H14B 110.6 . .
S1 C14 H14B 110.6 . .
H14A C14 H14B 108.7 . .
C20 C15 C16 119.4(3) . .
C20 C15 C14 119.9(3) . .
C16 C15 C14 120.7(3) . .
C17 C16 C15 120.7(3) . .
C17 C16 H16 119.6 . .
C15 C16 H16 119.6 . .
C18 C17 C16 118.2(3) . .
C18 C17 H17 120.9 . .
C16 C17 H17 120.9 . .
C17 C18 C19 122.6(3) . .
C17 C18 N4 118.5(3) . .
C19 C18 N4 118.8(3) . .
C18 C19 C20 118.4(3) . .
C18 C19 H19 120.8 . .
C20 C19 H19 120.8 . .
C15 C20 C19 120.6(3) . .
C15 C20 H20 119.7 . .
C19 C20 H20 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.756(3) .
S1 C14 1.830(3) .
O1 N4 1.221(4) .
O2 N4 1.229(4) .
N1 C1 1.323(4) .
N1 N2 1.386(4) .
N2 C2 1.306(4) .
N3 C1 1.364(4) .
N3 C2 1.371(4) .
N3 C13 1.455(4) .
N4 C18 1.469(4) .
C1 C3 1.511(4) .
C3 C4 1.543(4) .
C3 C10 1.546(4) .
C3 C8 1.548(4) .
C4 C5 1.533(4) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C12 1.528(4) .
C5 C6 1.531(4) .
C5 H5 1.0000 .
C6 C7 1.535(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C9 1.527(4) .
C7 C8 1.535(4) .
C7 H7 1.0000 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C11 1.531(4) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.530(4) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.533(4) .
C11 H11 1.0000 .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C15 1.509(4) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C20 1.392(5) .
C15 C16 1.392(5) .
C16 C17 1.389(4) .
C16 H16 0.9500 .
C17 C18 1.380(5) .
C17 H17 0.9500 .
C18 C19 1.380(5) .
C19 C20 1.387(4) .
C19 H19 0.9500 .
C20 H20 0.9500 .
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
C1 N1 N2 C2 0.6(4) . . . .
N2 N1 C1 N3 -0.7(4) . . . .
N2 N1 C1 C3 174.9(3) . . . .
C2 N3 C1 N1 0.5(3) . . . .
C13 N3 C1 N1 179.5(3) . . . .
C2 N3 C1 C3 -174.8(3) . . . .
C13 N3 C1 C3 4.2(5) . . . .
N1 N2 C2 N3 -0.2(4) . . . .
N1 N2 C2 S1 -174.1(2) . . . .
C1 N3 C2 N2 -0.2(4) . . . .
C13 N3 C2 N2 -179.2(3) . . . .
C1 N3 C2 S1 173.8(2) . . . .
C13 N3 C2 S1 -5.3(4) . . . .
C14 S1 C2 N2 -90.4(3) . . . .
C14 S1 C2 N3 96.5(3) . . . .
N1 C1 C3 C4 131.2(3) . . . .
N3 C1 C3 C4 -54.1(4) . . . .
N1 C1 C3 C10 11.3(4) . . . .
N3 C1 C3 C10 -173.9(3) . . . .
N1 C1 C3 C8 -105.9(3) . . . .
N3 C1 C3 C8 68.8(4) . . . .
C1 C3 C4 C5 -178.2(2) . . . .
C10 C3 C4 C5 -58.5(3) . . . .
C8 C3 C4 C5 58.4(3) . . . .
C3 C4 C5 C12 60.4(3) . . . .
C3 C4 C5 C6 -59.9(3) . . . .
C12 C5 C6 C7 -60.0(3) . . . .
C4 C5 C6 C7 60.3(3) . . . .
C5 C6 C7 C9 60.1(3) . . . .
C5 C6 C7 C8 -60.5(3) . . . .
C9 C7 C8 C3 -60.9(3) . . . .
C6 C7 C8 C3 59.4(3) . . . .
C1 C3 C8 C7 176.5(3) . . . .
C4 C3 C8 C7 -57.9(3) . . . .
C10 C3 C8 C7 59.2(3) . . . .
C8 C7 C9 C11 60.5(3) . . . .
C6 C7 C9 C11 -60.2(3) . . . .
C1 C3 C10 C11 -178.0(2) . . . .
C4 C3 C10 C11 58.5(3) . . . .
C8 C3 C10 C11 -59.3(3) . . . .
C3 C10 C11 C9 60.1(3) . . . .
C3 C10 C11 C12 -60.0(3) . . . .
C7 C9 C11 C10 -59.7(3) . . . .
C7 C9 C11 C12 60.3(3) . . . .
C6 C5 C12 C11 59.9(3) . . . .
C4 C5 C12 C11 -60.3(3) . . . .
C10 C11 C12 C5 60.0(3) . . . .
C9 C11 C12 C5 -60.0(3) . . . .
C2 S1 C14 C15 176.9(2) . . . .
S1 C14 C15 C20 97.9(3) . . . .
S1 C14 C15 C16 -80.8(3) . . . .
C20 C15 C16 C17 -0.7(5) . . . .
C14 C15 C16 C17 178.0(3) . . . .
C15 C16 C17 C18 0.4(5) . . . .
C16 C17 C18 C19 0.2(5) . . . .
C16 C17 C18 N4 179.6(3) . . . .
O1 N4 C18 C17 9.1(4) . . . .
O2 N4 C18 C17 -170.5(3) . . . .
O1 N4 C18 C19 -171.5(3) . . . .
O2 N4 C18 C19 8.9(4) . . . .
C17 C18 C19 C20 -0.6(5) . . . .
N4 C18 C19 C20 -179.9(3) . . . .
C16 C15 C20 C19 0.4(5) . . . .
C14 C15 C20 C19 -178.4(3) . . . .
C18 C19 C20 C15 0.3(5) . . . .
