#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/53/2215312.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_2215312
loop_
_publ_author_name
'Yunus, Uzma'
'Tahir, Mohammad Kalim'
'Bhatti, Moazzam Hussain'
'Ali, Saqib'
'Helliwell, Madeleine'
_publ_section_title
;
 2-Phenyl-4H-thiazolo[3,2-a][1,3,5]triazine-4-thione
;
_journal_coeditor_code           ZL2050
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3690
_journal_page_last               o3690
_journal_paper_doi               10.1107/S1600536807036963
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C11 H7 N3 S2'
_chemical_formula_moiety         'C11 H7 N3 S2'
_chemical_formula_sum            'C11 H7 N3 S2'
_chemical_formula_weight         245.32
_chemical_name_systematic
;
2-phenyl-4H-thiazolo[3,2-a][1,3,5]triazine-4-thione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 101.622(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.847(3)
_cell_length_b                   10.839(4)
_cell_length_c                   14.110(6)
_cell_measurement_reflns_used    4033
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.78
_cell_measurement_theta_min      2.38
_cell_volume                     1025.7(7)
_computing_cell_refinement       'CELL_NOW (Sheldrick, 2005)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001) and PLATON (Spek 2003)'
_computing_publication_material  'SHELXTL and PLATON'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  'not defined due to twin pairing errors'
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10242
_diffrn_reflns_theta_full        26.46
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS; Sheldrick, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0310
_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)+(0.0527P)²+0.056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                2486
_reflns_number_total             2777
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2050.cif
_cod_data_source_block           I
_cod_original_cell_volume        1025.6(7)
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2215312
_cod_database_fobs_code          2215312
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_refinement_flags
_atom_site_occupancy
S S1 0.08047(7) 0.93115(4) 0.21369(3) 0.01678(13) Uani d . 1
S S2 0.25020(9) 0.61499(4) 0.49345(3) 0.02268(15) Uani d . 1
N N1 0.1783(2) 0.79541(14) 0.36309(10) 0.0135(3) Uani d . 1
N N2 0.1877(2) 1.00925(14) 0.39873(11) 0.0147(3) Uani d . 1
N N3 0.2645(2) 0.85785(14) 0.52456(11) 0.0151(3) Uani d . 1
C C1 0.0830(3) 0.77317(18) 0.20055(14) 0.0177(4) Uani d . 1
H H1 0.0498 0.7322 0.1399 0.021 Uiso calc R 1
C C2 0.1368(3) 0.71478(18) 0.28516(14) 0.0172(4) Uani d . 1
H H2 0.1457 0.6276 0.2913 0.021 Uiso calc R 1
C C3 0.1563(3) 0.91697(17) 0.33755(14) 0.0142(4) Uani d . 1
C C4 0.2431(3) 0.97366(16) 0.49194(13) 0.0129(4) Uani d . 1
C C5 0.2320(3) 0.76289(17) 0.46220(13) 0.0146(4) Uani d . 1
C C6 0.2830(3) 1.07262(17) 0.56603(13) 0.0146(4) Uani d . 1
C C7 0.2579(3) 1.19652(18) 0.53972(14) 0.0182(4) Uani d . 1
H H7 0.2133 1.2184 0.4737 0.022 Uiso calc R 1
C C8 0.2981(3) 1.28779(19) 0.60983(15) 0.0221(4) Uani d . 1
H H8 0.2813 1.3721 0.5915 0.027 Uiso calc R 1
C C9 0.3625(3) 1.25680(19) 0.70655(15) 0.0211(4) Uani d . 1
H H9 0.3906 1.3198 0.7542 0.025 Uiso calc R 1
C C10 0.3858(3) 1.13343(18) 0.73370(14) 0.0194(4) Uani d . 1
H H10 0.4288 1.1117 0.7999 0.023 Uiso calc R 1
C C11 0.3459(3) 1.04248(18) 0.66347(14) 0.0173(4) Uani d . 1
H H11 0.3616 0.9582 0.6820 0.021 Uiso calc R 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
C1 S1 C3 90.74(9)
C3 N1 C2 113.83(15)
C3 N1 C5 119.54(15)
C2 N1 C5 126.58(16)
C3 N2 C4 113.60(16)
C4 N3 C5 120.16(16)
C2 C1 S1 112.43(15)
C2 C1 H1 123.8
S1 C1 H1 123.8
C1 C2 N1 112.65(17)
C1 C2 H2 123.7
N1 C2 H2 123.7
N2 C3 N1 124.59(17)
N2 C3 S1 125.08(15)
N1 C3 S1 110.33(13)
N3 C4 N2 126.49(17)
N3 C4 C6 116.41(17)
N2 C4 C6 117.10(15)
N3 C5 N1 115.57(16)
N3 C5 S2 124.90(15)
N1 C5 S2 119.53(14)
C11 C6 C7 119.02(18)
C11 C6 C4 120.11(17)
C7 C6 C4 120.87(17)
C8 C7 C6 120.06(19)
C8 C7 H7 120.0
C6 C7 H7 120.0
C7 C8 C9 120.45(19)
C7 C8 H8 119.8
C9 C8 H8 119.8
C8 C9 C10 119.96(19)
C8 C9 H9 120.0
C10 C9 H9 120.0
C11 C10 C9 119.45(19)
C11 C10 H10 120.3
C9 C10 H10 120.3
C10 C11 C6 121.06(18)
C10 C11 H11 119.5
C6 C11 H11 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.723(2)
S1 C3 1.727(2)
S2 C5 1.661(2)
N1 C3 1.366(2)
N1 C2 1.388(2)
N1 C5 1.417(2)
N2 C3 1.310(2)
N2 C4 1.350(2)
N3 C4 1.335(2)
N3 C5 1.343(2)
C1 C2 1.336(3)
C1 H1 0.9500
C2 H2 0.9500
C4 C6 1.484(3)
C6 C11 1.394(3)
C6 C7 1.395(3)
C7 C8 1.387(3)
C7 H7 0.9500
C8 C9 1.388(3)
C8 H8 0.9500
C9 C10 1.391(3)
C9 H9 0.9500
C10 C11 1.385(3)
C10 H10 0.9500
C11 H11 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
C3 S1 C1 C2 0.37(16)
S1 C1 C2 N1 -0.2(2)
C3 N1 C2 C1 -0.2(2)
C5 N1 C2 C1 177.56(18)
C4 N2 C3 N1 -0.7(3)
C4 N2 C3 S1 179.01(14)
C2 N1 C3 N2 -179.82(18)
C5 N1 C3 N2 2.3(3)
C2 N1 C3 S1 0.4(2)
C5 N1 C3 S1 -177.46(13)
C1 S1 C3 N2 179.80(18)
C1 S1 C3 N1 -0.44(15)
C5 N3 C4 N2 0.8(3)
C5 N3 C4 C6 -179.72(16)
C3 N2 C4 N3 -0.9(3)
C3 N2 C4 C6 179.61(16)
C4 N3 C5 N1 0.9(3)
C4 N3 C5 S2 -179.04(15)
C3 N1 C5 N3 -2.3(3)
C2 N1 C5 N3 -179.84(18)
C3 N1 C5 S2 177.64(14)
C2 N1 C5 S2 0.1(3)
N3 C4 C6 C11 2.1(3)
N2 C4 C6 C11 -178.31(17)
N3 C4 C6 C7 -177.70(17)
N2 C4 C6 C7 1.9(3)
C11 C6 C7 C8 0.9(3)
C4 C6 C7 C8 -179.29(18)
C6 C7 C8 C9 -0.3(3)
C7 C8 C9 C10 -0.5(3)
C8 C9 C10 C11 0.5(3)
C9 C10 C11 C6 0.1(3)
C7 C6 C11 C10 -0.8(3)
C4 C6 C11 C10 179.37(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123486
2 PubChem 46738451
