#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/74/2017450.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_2017450
loop_
_publ_author_name
'Hori, Akiko'
'Ishida, Yasuhide'
'Kikuchi, Takahiro'
'Miyamoto, Kumiko'
'Sakaguchi, Hiroshi'
_publ_section_title
;
 Two regioisomers of condensed thioheterocyclic triazine synthesized
 from 6-phenyl-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-5-one
;
_journal_coeditor_code           LN3135
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o593
_journal_page_last               o597
_journal_paper_doi               10.1107/S0108270109043728
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H9 N3 O S'
_chemical_formula_moiety         'C11 H9 N3 O S'
_chemical_formula_sum            'C11 H9 N3 O S'
_chemical_formula_weight         231.27
_chemical_name_systematic
;
3-phenyl-6,7-dihydro-4H-1,3-thiazolo[2,3-c][1,2,4]triazin-4-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 104.638(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.627(3)
_cell_length_b                   8.1222(10)
_cell_length_c                   11.8888(15)
_cell_measurement_reflns_used    4011
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      2.69
_cell_volume                     2020.6(5)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10860
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.9707
_exptl_absorpt_correction_T_min  0.9156
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.500
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0401
_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)+(0.0469P)²+1.0379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                3632
_reflns_number_total             4517
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ln3135.cif
_cod_data_source_block           III
_cod_original_cell_volume        2020.6(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017450
_cod_database_fobs_code          2017450
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.32791(10) 0.4391(3) 0.75224(19) 0.0355(5) Uani d . 1 . .
H H1A 0.3005 0.5351 0.7220 0.043 Uiso calc R 1 . .
H H1B 0.3195 0.4055 0.8271 0.043 Uiso calc R 1 . .
C C2 0.39778(8) 0.4846(2) 0.77028(15) 0.0222(4) Uani d . 1 . .
H H2A 0.4022 0.6052 0.7630 0.027 Uiso calc R 1 . .
H H2B 0.4223 0.4509 0.8489 0.027 Uiso calc R 1 . .
C C3 0.38304(8) 0.2888(2) 0.61371(15) 0.0191(4) Uani d . 1 . .
C C5 0.48389(8) 0.4270(2) 0.67158(14) 0.0188(4) Uani d . 1 . .
C C6 0.49918(8) 0.3229(2) 0.58033(14) 0.0174(3) Uani d . 1 . .
C C11 0.56367(8) 0.3248(2) 0.55718(14) 0.0181(3) Uani d . 1 . .
C C12 0.57745(9) 0.2090(2) 0.47880(15) 0.0213(4) Uani d . 1 . .
H H12 0.5454 0.1339 0.4404 0.026 Uiso calc R 1 . .
C C13 0.63739(9) 0.2040(2) 0.45735(16) 0.0250(4) Uani d . 1 . .
H H13 0.6462 0.1250 0.4045 0.030 Uiso calc R 1 . .
C C14 0.68486(9) 0.3135(2) 0.51242(16) 0.0255(4) Uani d . 1 . .
H H14 0.7260 0.3092 0.4977 0.031 Uiso calc R 1 . .
C C15 0.67157(9) 0.4288(2) 0.58891(16) 0.0245(4) Uani d . 1 . .
H H15 0.7037 0.5045 0.6262 0.029 Uiso calc R 1 . .
C C16 0.61167(8) 0.4350(2) 0.61172(15) 0.0204(4) Uani d . 1 . .
H H16 0.6033 0.5145 0.6646 0.024 Uiso calc R 1 . .
C C21 0.16178(10) 0.4367(4) 0.4046(2) 0.0523(7) Uani d . 1 . .
H H21A 0.1686 0.4002 0.4863 0.063 Uiso calc R 1 . .
H H21B 0.1899 0.5324 0.4032 0.063 Uiso calc R 1 . .
C C22 0.09343(9) 0.4853(2) 0.35684(15) 0.0254(4) Uani d . 1 . .
H H22A 0.0678 0.4531 0.4116 0.031 Uiso calc R 1 . .
H H22B 0.0901 0.6060 0.3456 0.031 Uiso calc R 1 . .
C C23 0.10903(8) 0.2906(2) 0.21353(15) 0.0202(4) Uani d . 1 . .
C C25 0.00847(8) 0.4299(2) 0.17702(15) 0.0194(4) Uani d . 1 . .
C C26 -0.00682(8) 0.3257(2) 0.07212(14) 0.0183(3) Uani d . 1 . .
C C31 -0.07151(8) 0.3247(2) -0.00950(15) 0.0190(4) Uani d . 1 . .
C C32 -0.08497(9) 0.2097(2) -0.10055(16) 0.0249(4) Uani d . 1 . .
H H32 -0.0524 0.1370 -0.1105 0.030 Uiso calc R 1 . .
C C33 -0.14525(10) 0.2010(2) -0.17605(17) 0.0294(4) Uani d . 1 . .
H H33 -0.1537 0.1223 -0.2372 0.035 Uiso calc R 1 . .
C C34 -0.19334(9) 0.3062(2) -0.16294(18) 0.0308(5) Uani d . 1 . .
H H34 -0.2346 0.3000 -0.2148 0.037 Uiso calc R 1 . .
C C35 -0.18082(9) 0.4205(3) -0.07368(18) 0.0300(4) Uani d . 1 . .
H H35 -0.2138 0.4928 -0.0646 0.036 Uiso calc R 1 . .
C C36 -0.12059(9) 0.4308(2) 0.00275(17) 0.0246(4) Uani d . 1 . .
H H36 -0.1126 0.5099 0.0635 0.030 Uiso calc R 1 . .
N N1 0.45743(7) 0.22165(18) 0.51665(13) 0.0201(3) Uani d . 1 . .
N N2 0.39686(7) 0.20253(18) 0.53141(13) 0.0218(3) Uani d . 1 . .
N N4 0.42228(7) 0.39948(17) 0.68153(12) 0.0183(3) Uani d . 1 . .
N N21 0.03514(7) 0.22516(18) 0.04688(13) 0.0211(3) Uani d . 1 . .
N N22 0.09563(7) 0.20606(18) 0.11785(13) 0.0227(3) Uani d . 1 . .
N N24 0.06947(7) 0.40080(18) 0.24500(12) 0.0189(3) Uani d . 1 . .
O O1 0.51799(6) 0.52754(16) 0.73436(11) 0.0248(3) Uani d . 1 . .
O O2 -0.02550(6) 0.53237(16) 0.20753(11) 0.0270(3) Uani d . 1 . .
S S1 0.30970(2) 0.26990(6) 0.64887(4) 0.02690(13) Uani d . 1 . .
S S2 0.18175(2) 0.27044(6) 0.31750(4) 0.02798(13) Uani d . 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'
O O 0.0106 0.0060 '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
C2 C1 S1 . . 108.52(13) ?
C2 C1 H1A . . 110.0 ?
S1 C1 H1A . . 110.0 ?
C2 C1 H1B . . 110.0 ?
S1 C1 H1B . . 110.0 ?
H1A C1 H1B . . 108.4 ?
N4 C2 C1 . . 108.11(15) ?
N4 C2 H2A . . 110.1 ?
C1 C2 H2A . . 110.1 ?
N4 C2 H2B . . 110.1 ?
C1 C2 H2B . . 110.1 ?
H2A C2 H2B . . 108.4 ?
N2 C3 N4 . . 125.33(16) ?
N2 C3 S1 . . 121.94(13) ?
N4 C3 S1 . . 112.73(13) ?
O1 C5 N4 . . 120.07(16) ?
O1 C5 C6 . . 128.26(16) ?
N4 C5 C6 . . 111.66(14) ?
N1 C6 C5 . . 122.25(16) ?
N1 C6 C11 . . 116.14(15) ?
C5 C6 C11 . . 121.60(15) ?
C16 C11 C12 . . 118.52(16) ?
C16 C11 C6 . . 122.74(16) ?
C12 C11 C6 . . 118.72(15) ?
C13 C12 C11 . . 120.45(17) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C12 C13 C14 . . 120.59(17) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
C15 C14 C13 . . 119.37(18) ?
C15 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
C14 C15 C16 . . 120.73(17) ?
C14 C15 H15 . . 119.6 ?
C16 C15 H15 . . 119.6 ?
C15 C16 C11 . . 120.34(17) ?
C15 C16 H16 . . 119.8 ?
C11 C16 H16 . . 119.8 ?
C22 C21 S2 . . 109.48(15) ?
C22 C21 H21A . . 109.8 ?
S2 C21 H21A . . 109.8 ?
C22 C21 H21B . . 109.8 ?
S2 C21 H21B . . 109.8 ?
H21A C21 H21B . . 108.2 ?
N24 C22 C21 . . 108.00(16) ?
N24 C22 H22A . . 110.1 ?
C21 C22 H22A . . 110.1 ?
N24 C22 H22B . . 110.1 ?
C21 C22 H22B . . 110.1 ?
H22A C22 H22B . . 108.4 ?
N22 C23 N24 . . 125.13(16) ?
N22 C23 S2 . . 122.19(14) ?
N24 C23 S2 . . 112.68(13) ?
O2 C25 N24 . . 119.91(16) ?
O2 C25 C26 . . 128.18(16) ?
N24 C25 C26 . . 111.91(14) ?
N21 C26 C25 . . 122.10(16) ?
N21 C26 C31 . . 116.03(15) ?
C25 C26 C31 . . 121.85(15) ?
C36 C31 C32 . . 118.28(16) ?
C36 C31 C26 . . 122.72(16) ?
C32 C31 C26 . . 118.97(16) ?
C33 C32 C31 . . 120.78(18) ?
C33 C32 H32 . . 119.6 ?
C31 C32 H32 . . 119.6 ?
C32 C33 C34 . . 120.39(19) ?
C32 C33 H33 . . 119.8 ?
C34 C33 H33 . . 119.8 ?
C35 C34 C33 . . 119.56(18) ?
C35 C34 H34 . . 120.2 ?
C33 C34 H34 . . 120.2 ?
C34 C35 C36 . . 120.72(19) ?
C34 C35 H35 . . 119.6 ?
C36 C35 H35 . . 119.6 ?
C35 C36 C31 . . 120.28(18) ?
C35 C36 H36 . . 119.9 ?
C31 C36 H36 . . 119.9 ?
C6 N1 N2 . . 122.47(15) ?
C3 N2 N1 . . 116.35(14) ?
C3 N4 C5 . . 121.87(15) ?
C3 N4 C2 . . 117.08(15) ?
C5 N4 C2 . . 121.00(14) ?
C26 N21 N22 . . 122.44(15) ?
C23 N22 N21 . . 116.45(15) ?
C23 N24 C25 . . 121.85(15) ?
C23 N24 C22 . . 117.10(15) ?
C25 N24 C22 . . 121.03(14) ?
C3 S1 C1 . . 92.33(9) ?
C23 S2 C21 . . 91.86(9) ?
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
C1 C2 . 1.518(3) ?
C1 S1 . 1.819(2) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 N4 . 1.468(2) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 N2 . 1.298(2) ?
C3 N4 . 1.354(2) ?
C3 S1 . 1.7462(18) ?
C5 O1 . 1.221(2) ?
C5 N4 . 1.385(2) ?
C5 C6 . 1.477(2) ?
C6 N1 . 1.311(2) ?
C6 C11 . 1.488(2) ?
C11 C16 . 1.400(2) ?
C11 C12 . 1.408(2) ?
C12 C13 . 1.383(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.391(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.385(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.390(3) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C22 . 1.496(3) ?
C21 S2 . 1.819(2) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 N24 . 1.469(2) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 N22 . 1.297(2) ?
C23 N24 . 1.354(2) ?
C23 S2 . 1.7452(18) ?
C25 O2 . 1.224(2) ?
C25 N24 . 1.382(2) ?
C25 C26 . 1.474(2) ?
C26 N21 . 1.311(2) ?
C26 C31 . 1.488(2) ?
C31 C36 . 1.403(2) ?
C31 C32 . 1.403(3) ?
C32 C33 . 1.385(3) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.385(3) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.384(3) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.390(3) ?
C35 H35 . 0.9500 ?
C36 H36 . 0.9500 ?
N1 N2 . 1.374(2) ?
N21 N22 . 1.375(2) ?
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
C2 H2B N1 4_566 0.99 2.40 3.338(2) 158
C22 H22A N21 4_566 0.99 2.40 3.325(2) 155
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
S1 C1 C2 N4 . . . . 11.09(19) ?
O1 C5 C6 N1 . . . . -178.37(17) ?
N4 C5 C6 N1 . . . . 1.6(2) ?
O1 C5 C6 C11 . . . . 2.9(3) ?
N4 C5 C6 C11 . . . . -177.11(14) ?
N1 C6 C11 C16 . . . . 175.00(16) ?
C5 C6 C11 C16 . . . . -6.2(2) ?
N1 C6 C11 C12 . . . . -6.2(2) ?
C5 C6 C11 C12 . . . . 172.59(15) ?
C16 C11 C12 C13 . . . . 0.6(2) ?
C6 C11 C12 C13 . . . . -178.27(15) ?
C11 C12 C13 C14 . . . . -0.3(3) ?
C12 C13 C14 C15 . . . . -0.3(3) ?
C13 C14 C15 C16 . . . . 0.6(3) ?
C14 C15 C16 C11 . . . . -0.2(3) ?
C12 C11 C16 C15 . . . . -0.3(2) ?
C6 C11 C16 C15 . . . . 178.48(16) ?
S2 C21 C22 N24 . . . . -9.3(2) ?
O2 C25 C26 N21 . . . . 176.96(17) ?
N24 C25 C26 N21 . . . . -3.2(2) ?
O2 C25 C26 C31 . . . . -5.0(3) ?
N24 C25 C26 C31 . . . . 174.86(14) ?
N21 C26 C31 C36 . . . . -176.93(16) ?
C25 C26 C31 C36 . . . . 4.9(3) ?
N21 C26 C31 C32 . . . . 5.2(2) ?
C25 C26 C31 C32 . . . . -173.03(16) ?
C36 C31 C32 C33 . . . . -0.2(3) ?
C26 C31 C32 C33 . . . . 177.78(16) ?
C31 C32 C33 C34 . . . . 0.1(3) ?
C32 C33 C34 C35 . . . . 0.0(3) ?
C33 C34 C35 C36 . . . . 0.0(3) ?
C34 C35 C36 C31 . . . . -0.1(3) ?
C32 C31 C36 C35 . . . . 0.2(3) ?
C26 C31 C36 C35 . . . . -177.71(16) ?
C5 C6 N1 N2 . . . . -1.2(2) ?
C11 C6 N1 N2 . . . . 177.55(14) ?
N4 C3 N2 N1 . . . . 3.0(3) ?
S1 C3 N2 N1 . . . . -176.36(12) ?
C6 N1 N2 C3 . . . . -1.0(2) ?
N2 C3 N4 C5 . . . . -2.6(3) ?
S1 C3 N4 C5 . . . . 176.81(12) ?
N2 C3 N4 C2 . . . . -179.91(16) ?
S1 C3 N4 C2 . . . . -0.53(19) ?
O1 C5 N4 C3 . . . . -179.86(15) ?
C6 C5 N4 C3 . . . . 0.2(2) ?
O1 C5 N4 C2 . . . . -2.6(2) ?
C6 C5 N4 C2 . . . . 177.41(14) ?
C1 C2 N4 C3 . . . . -7.2(2) ?
C1 C2 N4 C5 . . . . 175.47(16) ?
C25 C26 N21 N22 . . . . 2.0(3) ?
C31 C26 N21 N22 . . . . -176.22(14) ?
N24 C23 N22 N21 . . . . -3.5(3) ?
S2 C23 N22 N21 . . . . 175.74(12) ?
C26 N21 N22 C23 . . . . 1.4(2) ?
N22 C23 N24 C25 . . . . 2.1(3) ?
S2 C23 N24 C25 . . . . -177.25(12) ?
N22 C23 N24 C22 . . . . -179.70(17) ?
S2 C23 N24 C22 . . . . 0.97(19) ?
O2 C25 N24 C23 . . . . -178.85(16) ?
C26 C25 N24 C23 . . . . 1.3(2) ?
O2 C25 N24 C22 . . . . 3.0(2) ?
C26 C25 N24 C22 . . . . -176.83(15) ?
C21 C22 N24 C23 . . . . 5.7(2) ?
C21 C22 N24 C25 . . . . -176.11(18) ?
N2 C3 S1 C1 . . . . -174.21(16) ?
N4 C3 S1 C1 . . . . 6.39(14) ?
C2 C1 S1 C3 . . . . -10.07(15) ?
N22 C23 S2 C21 . . . . 174.95(18) ?
N24 C23 S2 C21 . . . . -5.69(15) ?
C22 C21 S2 C23 . . . . 8.69(19) ?
