#------------------------------------------------------------------------------
#$Date: 2023-08-24 04:45:48 +0300 (Thu, 24 Aug 2023) $
#$Revision: 285858 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022846.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_2022846
loop_
_publ_author_name
'Azzam, Rasha A.'
'Elgemeie, Galal H.'
'Elboshi, Heba A.'
'Jones, Peter G.'
_publ_section_title
;
 Crystal structure of
 2-{[5-(methylsulfanyl)-4-phenyl-4H-1,2,4-triazol-3-yl]methyl}benzo[d]thiazole
;
_journal_coeditor_code           YZ2038
_journal_issue                   9
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989023007041
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C17 H14 N4 S2'
_chemical_formula_moiety         'C17 H14 N4 S2'
_chemical_formula_sum            'C17 H14 N4 S2'
_chemical_formula_weight         338.44
_chemical_name_systematic
2-{[5-(Methylsulfanyl)-4-phenyl-4H-1,2,4-triazol-3-yl]methyl}benzo[d]thiazole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                94.088(2)
_cell_angle_beta                 105.954(2)
_cell_angle_gamma                107.393(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9714(2)
_cell_length_b                   9.3564(3)
_cell_length_c                   10.4969(2)
_cell_measurement_reflns_used    69237
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      41.4020
_cell_measurement_theta_min      2.3000
_cell_volume                     797.05(4)
_computing_cell_refinement
;
CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL2019/3 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2019/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            102462
_diffrn_reflns_theta_full        40.000
_diffrn_reflns_theta_max         41.217
_diffrn_reflns_theta_min         2.047
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       tablet
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.254
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         10466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0528P)²+0.0903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                9289
_reflns_number_total             10466
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2038sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        797.05(3)
_cod_database_code               2022846
_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   0.945
_shelx_estimated_absorpt_t_max   0.967
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.86054(2) 0.48129(2) 0.77843(2) 0.01557(3) Uani d 1 . .
S S2 0.40521(2) 0.21180(2) 0.21857(2) 0.01692(3) Uani d 1 . .
N N1 0.69326(5) 0.14743(5) 0.54398(4) 0.01461(6) Uani d 1 . .
N N2 0.64593(5) 0.14656(5) 0.40548(4) 0.01439(6) Uani d 1 . .
N N3 0.65416(5) 0.41599(5) 0.91486(4) 0.01501(6) Uani d 1 . .
N N4 0.47354(4) 0.21828(4) 0.48932(4) 0.01123(5) Uani d 1 . .
C C2 0.68997(5) 0.36293(5) 0.81379(5) 0.01319(6) Uani d 1 . .
C C3A 0.76637(6) 0.55937(6) 0.97489(5) 0.01493(7) Uani d 1 . .
C C4 0.76214(7) 0.64760(7) 1.08644(6) 0.02094(9) Uani d 1 . .
H H4 0.678550 0.611765 1.127062 0.025 Uiso calc 1 . .
C C5 0.88296(8) 0.78864(7) 1.13624(6) 0.02484(10) Uani d 1 . .
H H5 0.882744 0.849356 1.212644 0.030 Uiso calc 1 . .
C C6 1.00541(8) 0.84304(7) 1.07564(7) 0.02362(10) Uani d 1 . .
H H6 1.086509 0.940173 1.111582 0.028 Uiso calc 1 . .
C C7 1.01035(7) 0.75745(6) 0.96388(6) 0.02010(9) Uani d 1 . .
H H7 1.092893 0.794830 0.922535 0.024 Uiso calc 1 . .
C C7A 0.88963(6) 0.61445(5) 0.91440(5) 0.01491(7) Uani d 1 . .
C C8 0.59619(6) 0.20550(5) 0.73494(5) 0.01490(7) Uani d 1 . .
H H8A 0.647569 0.133827 0.778009 0.018 Uiso calc 1 . .
H H8B 0.482421 0.175752 0.739460 0.018 Uiso calc 1 . .
C C9 0.58961(5) 0.18991(5) 0.59118(5) 0.01228(6) Uani d 1 . .
C C10 0.51471(5) 0.18851(5) 0.37612(5) 0.01212(6) Uani d 1 . .
C C11 0.54143(10) 0.18497(8) 0.12746(7) 0.02628(11) Uani d 1 . .
H H11A 0.500730 0.200775 0.034712 0.039 Uiso calc 1 . .
H H11B 0.545540 0.081470 0.127332 0.039 Uiso calc 1 . .
H H11C 0.651920 0.258121 0.170908 0.039 Uiso calc 1 . .
C C12 0.33320(5) 0.25713(5) 0.49752(5) 0.01169(6) Uani d 1 . .
C C13 0.17638(6) 0.15400(5) 0.43243(6) 0.01604(7) Uani d 1 . .
H H13 0.162422 0.059676 0.382357 0.019 Uiso calc 1 . .
C C14 0.04025(6) 0.19174(6) 0.44212(6) 0.01850(8) Uani d 1 . .
H H14 -0.067511 0.123172 0.397683 0.022 Uiso calc 1 . .
C C15 0.06206(6) 0.32983(6) 0.51686(6) 0.01743(8) Uani d 1 . .
H H15 -0.030950 0.354811 0.523584 0.021 Uiso calc 1 . .
C C16 0.21950(6) 0.43126(6) 0.58166(5) 0.01627(7) Uani d 1 . .
H H16 0.233522 0.525098 0.632575 0.020 Uiso calc 1 . .
C C17 0.35680(6) 0.39572(5) 0.57216(5) 0.01364(7) Uani d 1 . .
H H17 0.464502 0.464813 0.615821 0.016 Uiso calc 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 0.0000 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7A S1 C2 . . 88.86(2) y
C10 S2 C11 . . 98.33(3) y
C9 N1 N2 . . 107.60(4) y
C10 N2 N1 . . 106.63(4) y
C2 N3 C3A . . 110.40(4) y
C10 N4 C9 . . 104.30(4) y
C10 N4 C12 . . 127.66(4) ?
C9 N4 C12 . . 127.84(4) ?
N3 C2 C8 . . 122.28(4) ?
N3 C2 S1 . . 116.30(4) y
C8 C2 S1 . . 121.35(3) ?
N3 C3A C4 . . 124.68(5) ?
N3 C3A C7A . . 115.00(4) ?
C4 C3A C7A . . 120.32(5) ?
C5 C4 C3A . . 118.40(6) ?
C4 C5 C6 . . 121.08(6) ?
C7 C6 C5 . . 121.24(5) ?
C6 C7 C7A . . 117.76(5) ?
C7 C7A C3A . . 121.20(5) ?
C7 C7A S1 . . 129.37(4) ?
C3A C7A S1 . . 109.43(3) ?
C9 C8 C2 . . 114.28(4) y
N1 C9 N4 . . 110.51(4) y
N1 C9 C8 . . 124.86(4) ?
N4 C9 C8 . . 124.63(4) ?
N2 C10 N4 . . 110.97(4) y
N2 C10 S2 . . 126.93(4) ?
N4 C10 S2 . . 122.07(3) ?
C17 C12 C13 . . 121.63(4) ?
C17 C12 N4 . . 119.25(4) ?
C13 C12 N4 . . 119.12(4) ?
C12 C13 C14 . . 118.84(4) ?
C15 C14 C13 . . 120.14(5) ?
C16 C15 C14 . . 120.28(4) ?
C15 C16 C17 . . 120.28(4) ?
C12 C17 C16 . . 118.83(4) ?
C5 C4 H4 . . 120.8 ?
C3A C4 H4 . . 120.8 ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C7 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
C6 C7 H7 . . 121.1 ?
C7A C7 H7 . . 121.1 ?
C9 C8 H8A . . 108.7 ?
C2 C8 H8A . . 108.7 ?
C9 C8 H8B . . 108.7 ?
C2 C8 H8B . . 108.7 ?
H8A C8 H8B . . 107.6 ?
S2 C11 H11A . . 109.5 ?
S2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
S2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C12 C17 H17 . . 120.6 ?
C16 C17 H17 . . 120.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7A . 1.7334(5) y
S1 C2 . 1.7503(5) y
S2 C10 . 1.7418(5) y
S2 C11 . 1.8063(6) y
N1 C9 . 1.3094(6) y
N1 N2 . 1.3968(6) y
N2 C10 . 1.3150(6) y
N3 C2 . 1.2973(6) y
N3 C3A . 1.3905(7) y
N4 C10 . 1.3716(6) y
N4 C9 . 1.3754(6) y
N4 C12 . 1.4330(5) ?
C2 C8 . 1.5050(7) ?
C3A C4 . 1.3997(7) ?
C3A C7A . 1.4084(7) ?
C4 C5 . 1.3873(9) ?
C5 C6 . 1.4023(10) ?
C6 C7 . 1.3912(9) ?
C7 C7A . 1.3994(7) ?
C8 C9 . 1.4887(7) ?
C12 C17 . 1.3928(6) ?
C12 C13 . 1.3940(6) ?
C13 C14 . 1.3955(7) ?
C14 C15 . 1.3939(7) ?
C15 C16 . 1.3917(7) ?
C16 C17 . 1.3948(6) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
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
_geom_hbond_publ_flag
C11 H11A N3 1_554 0.98 2.68 3.3610(8) 126.8 yes
C13 H13 N1 2_656 0.95 2.68 3.3609(6) 128.9 yes
C14 H14 N2 1_455 0.95 2.67 3.3431(6) 128.6 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 N2 C10 . . . . -0.19(5) ?
C3A N3 C2 C8 . . . . 175.98(4) ?
C3A N3 C2 S1 . . . . -1.04(5) ?
C7A S1 C2 N3 . . . . 1.07(4) ?
C7A S1 C2 C8 . . . . -175.98(4) ?
C2 N3 C3A C4 . . . . 179.97(5) ?
C2 N3 C3A C7A . . . . 0.43(6) ?
N3 C3A C4 C5 . . . . 179.66(5) ?
C7A C3A C4 C5 . . . . -0.82(8) ?
C3A C4 C5 C6 . . . . 0.86(9) ?
C4 C5 C6 C7 . . . . -0.20(10) ?
C5 C6 C7 C7A . . . . -0.49(9) ?
C6 C7 C7A C3A . . . . 0.52(8) ?
C6 C7 C7A S1 . . . . 179.73(4) ?
N3 C3A C7A C7 . . . . 179.70(5) ?
C4 C3A C7A C7 . . . . 0.13(8) ?
N3 C3A C7A S1 . . . . 0.35(5) ?
C4 C3A C7A S1 . . . . -179.22(4) ?
C2 S1 C7A C7 . . . . 179.99(5) ?
C2 S1 C7A C3A . . . . -0.73(4) ?
N3 C2 C8 C9 . . . . 149.86(5) ?
S1 C2 C8 C9 . . . . -33.27(6) ?
N2 N1 C9 N4 . . . . -0.13(5) ?
N2 N1 C9 C8 . . . . 179.90(4) ?
C10 N4 C9 N1 . . . . 0.39(5) ?
C12 N4 C9 N1 . . . . 175.49(4) ?
C10 N4 C9 C8 . . . . -179.64(4) ?
C12 N4 C9 C8 . . . . -4.54(7) ?
C2 C8 C9 N1 . . . . 93.15(6) ?
C2 C8 C9 N4 . . . . -86.82(5) ?
N1 N2 C10 N4 . . . . 0.44(5) ?
N1 N2 C10 S2 . . . . 178.46(3) ?
C9 N4 C10 N2 . . . . -0.51(5) ?
C12 N4 C10 N2 . . . . -175.63(4) ?
C9 N4 C10 S2 . . . . -178.64(3) ?
C12 N4 C10 S2 . . . . 6.24(6) ?
C11 S2 C10 N2 . . . . -6.70(5) ?
C11 S2 C10 N4 . . . . 171.12(4) ?
C10 N4 C12 C17 . . . . -119.71(5) ?
C9 N4 C12 C17 . . . . 66.28(6) ?
C10 N4 C12 C13 . . . . 61.39(6) ?
C9 N4 C12 C13 . . . . -112.62(5) ?
C17 C12 C13 C14 . . . . 0.38(8) ?
N4 C12 C13 C14 . . . . 179.25(5) ?
C12 C13 C14 C15 . . . . -0.59(8) ?
C13 C14 C15 C16 . . . . 0.35(9) ?
C14 C15 C16 C17 . . . . 0.12(8) ?
C13 C12 C17 C16 . . . . 0.08(7) ?
N4 C12 C17 C16 . . . . -178.79(4) ?
C15 C16 C17 C12 . . . . -0.33(7) ?

_cod_database_fobs_code 2022846
