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#$Date: 2022-11-28 10:33:08 +0200 (Mon, 28 Nov 2022) $
#$Revision: 279587 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106266.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_8106266
loop_
_publ_author_name
'Aouad, Mohamed Reda'
'Messali, Mouslim'
'Rezki, Nadjet'
'Shivalingegowda, Naveen'
'Warad, Ismail'
_publ_section_title
;
 Crystal structure of
 4-phenyl-3-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)-1H-1,2,4-triazole-5(4H)-thione,
 C17H14N6S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              697
_journal_page_last               698
_journal_paper_doi               10.1515/ncrs-2018-0025
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C17 H14 N6 S'
_chemical_formula_weight         334.40
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3832(3)
_cell_length_b                   14.4702(7)
_cell_length_c                   15.2806(7)
_cell_measurement_reflns_used    2848
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.57
_cell_measurement_theta_min      5.79
_cell_volume                     1632.52(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       '\\\f and \\\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28809
_diffrn_reflns_theta_full        66.57
_diffrn_reflns_theta_max         66.57
_diffrn_reflns_theta_min         5.79
_exptl_absorpt_coefficient_mu    1.849
_exptl_absorpt_correction_T_max  0.6865
_exptl_absorpt_correction_T_min  0.6256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rectangle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0717P)²+0.0697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                2848
_reflns_number_total             2869
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2018-0025_suppl.cif
_cod_data_source_block           SHELXL
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               8106266
_publcif_funding_html
;
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.02291(6) -0.68235(3) -0.89262(4) 0.06769(16) Uani 1 1 d . . .
N1 N -0.33020(17) -0.78853(8) -0.87530(8) 0.0480(3) Uani 1 1 d . . .
N2 N -0.38008(19) -0.64350(9) -0.88009(9) 0.0550(3) Uani 1 1 d . . .
H2 H -0.3640 -0.5847 -0.8833 0.066 Uiso 1 1 calc R . .
N3 N -0.54711(18) -0.68324(9) -0.87164(9) 0.0531(3) Uani 1 1 d . . .
N4 N -0.68993(17) -0.86710(9) -0.76957(8) 0.0498(3) Uani 1 1 d . . .
C10 C -0.7623(2) -0.81429(11) -0.70616(10) 0.0542(3) Uani 1 1 d . . .
H10 H -0.8064 -0.7543 -0.7112 0.065 Uiso 1 1 calc R . .
N6 N -0.6413(2) -0.94984(9) -0.73887(9) 0.0595(3) Uani 1 1 d . . .
C1 C -0.2441(2) -0.70438(10) -0.88287(9) 0.0513(3) Uani 1 1 d . . .
N5 N -0.6828(2) -0.95080(9) -0.65555(9) 0.0588(3) Uani 1 1 d . . .
C3 C -0.2396(2) -0.87673(10) -0.87094(10) 0.0514(3) Uani 1 1 d . . .
C2 C -0.5139(2) -0.77161(10) -0.86984(9) 0.0482(3) Uani 1 1 d . . .
C17 C -0.8854(3) -0.91398(13) -0.48846(12) 0.0674(4) Uani 1 1 d . . .
H17 H -0.9119 -0.9720 -0.5113 0.081 Uiso 1 1 calc R . .
C12 C -0.8083(2) -0.84733(12) -0.54128(10) 0.0549(4) Uani 1 1 d . . .
C9 C -0.6575(2) -0.84319(11) -0.86167(9) 0.0513(3) Uani 1 1 d . . .
H9A H -0.7688 -0.8203 -0.8875 0.062 Uiso 1 1 calc R . .
H9B H -0.6213 -0.8982 -0.8935 0.062 Uiso 1 1 calc R . .
C11 C -0.7570(2) -0.86804(10) -0.63250(10) 0.0517(3) Uani 1 1 d . . .
C8 C -0.2012(3) -0.91491(14) -0.79070(13) 0.0743(5) Uani 1 1 d . . .
H8 H -0.2367 -0.8849 -0.7397 0.089 Uiso 1 1 calc R . .
C16 C -0.9232(3) -0.89474(16) -0.40187(13) 0.0787(6) Uani 1 1 d . . .
H16 H -0.9772 -0.9395 -0.3668 0.094 Uiso 1 1 calc R . .
C4 C -0.1890(3) -0.92074(13) -0.94624(13) 0.0674(4) Uani 1 1 d . . .
H4 H -0.2152 -0.8949 -1.0005 0.081 Uiso 1 1 calc R . .
C5 C -0.0984(4) -1.00414(16) -0.94056(18) 0.0884(6) Uani 1 1 d . . .
H5 H -0.0640 -1.0347 -0.9914 0.106 Uiso 1 1 calc R . .
C14 C -0.8082(4) -0.74174(19) -0.42030(14) 0.0871(6) Uani 1 1 d . . .
H14 H -0.7838 -0.6835 -0.3975 0.104 Uiso 1 1 calc R . .
C6 C -0.0589(3) -1.04186(14) -0.86126(19) 0.0870(7) Uani 1 1 d . . .
H6 H 0.0029 -1.0978 -0.8582 0.104 Uiso 1 1 calc R . .
C13 C -0.7714(3) -0.76039(14) -0.50696(13) 0.0714(5) Uani 1 1 d . . .
H13 H -0.7218 -0.7148 -0.5425 0.086 Uiso 1 1 calc R . .
C15 C -0.8811(3) -0.80935(19) -0.36726(12) 0.0835(6) Uani 1 1 d . . .
H15 H -0.9018 -0.7974 -0.3083 0.100 Uiso 1 1 calc R . .
C7 C -0.1099(4) -0.99780(17) -0.78625(18) 0.0924(7) Uani 1 1 d . . .
H7 H -0.0830 -1.0237 -0.7321 0.111 Uiso 1 1 calc R . .
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
C1 N1 C2 107.55(12) . .
C1 N1 C3 124.86(13) . .
C2 N1 C3 127.55(13) . .
C1 N2 N3 113.80(12) . .
C2 N3 N2 104.21(12) . .
N6 N4 C10 111.30(12) . .
N6 N4 C9 120.27(13) . .
C10 N4 C9 128.41(13) . .
N4 C10 C11 104.97(13) . .
N5 N6 N4 106.75(13) . .
N2 C1 N1 103.48(13) . .
N2 C1 S1 127.70(12) . .
N1 C1 S1 128.82(12) . .
N6 N5 C11 109.62(13) . .
C4 C3 C8 120.49(16) . .
C4 C3 N1 120.00(14) . .
C8 C3 N1 119.50(15) . .
N3 C2 N1 110.95(13) . .
N3 C2 C9 123.47(14) . .
N1 C2 C9 125.57(13) . .
C16 C17 C12 120.19(19) . .
C17 C12 C13 119.52(17) . .
C17 C12 C11 121.10(16) . .
C13 C12 C11 119.33(16) . .
N4 C9 C2 111.13(12) . .
N5 C11 C10 107.36(13) . .
N5 C11 C12 121.72(14) . .
C10 C11 C12 130.86(14) . .
C3 C8 C7 119.7(2) . .
C15 C16 C17 120.2(2) . .
C3 C4 C5 119.08(19) . .
C6 C5 C4 120.6(2) . .
C13 C14 C15 120.2(2) . .
C5 C6 C7 120.10(19) . .
C14 C13 C12 120.1(2) . .
C16 C15 C14 119.86(18) . .
C6 C7 C8 120.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.6704(16) .
N1 C1 1.378(2) .
N1 C2 1.381(2) .
N1 C3 1.4426(19) .
N2 C1 1.336(2) .
N2 N3 1.367(2) .
N3 C2 1.302(2) .
N4 N6 1.3352(19) .
N4 C10 1.345(2) .
N4 C9 1.4688(19) .
C10 C11 1.369(2) .
N6 N5 1.3096(19) .
N5 C11 1.363(2) .
C3 C4 1.367(3) .
C3 C8 1.374(2) .
C2 C9 1.487(2) .
C17 C16 1.381(3) .
C17 C12 1.380(3) .
C12 C13 1.390(3) .
C12 C11 1.475(2) .
C8 C7 1.378(3) .
C16 C15 1.379(4) .
C4 C5 1.383(3) .
C5 C6 1.361(4) .
C14 C13 1.379(3) .
C14 C15 1.380(4) .
C6 C7 1.365(4) .
