#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/74/2017449.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_2017449
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
;
6-phenyl-2,3-dihydro-7H-1,3-thiazolo[3,2-b][1,2,4]triazin-7-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.3630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1257(4)
_cell_length_b                   11.3239(5)
_cell_length_c                   11.3860(5)
_cell_measurement_reflns_used    4742
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.55
_cell_volume                     1033.72(8)
_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 0.970
_diffrn_measured_fraction_theta_max 0.970
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5756
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.9439
_exptl_absorpt_correction_T_min  0.8797
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.203
_refine_ls_abs_structure_details
'Flack & Bernardinelli (2000), 577 Friedel pairs'
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0236
_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)+(0.0362P)²+0.2617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0609
_reflns_number_gt                2939
_reflns_number_total             2992
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ln3135.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2017449
_cod_database_fobs_code          2017449
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4266(2) 1.06970(19) 0.56607(16) 0.0209(4) Uani d . 1 . .
H H1A 0.3673 1.1334 0.6016 0.025 Uiso calc R 1 . .
H H1B 0.5394 1.0609 0.6135 0.025 Uiso calc R 1 . .
C C2 0.4386(2) 1.09884(18) 0.43657(16) 0.0208(4) Uani d . 1 . .
H H2A 0.3438 1.1489 0.4007 0.025 Uiso calc R 1 . .
H H2B 0.5440 1.1409 0.4313 0.025 Uiso calc R 1 . .
C C3 0.3606(2) 0.89446(17) 0.42480(14) 0.0158(3) Uani d . 1 . .
C C5 0.3652(2) 0.77605(17) 0.26161(15) 0.0171(3) Uani d . 1 . .
C C6 0.4402(2) 0.87934(17) 0.20820(15) 0.0148(3) Uani d . 1 . .
C C11 0.4838(2) 0.87549(17) 0.08656(15) 0.0155(3) Uani d . 1 . .
C C12 0.6080(2) 0.95126(17) 0.05781(15) 0.0180(4) Uani d . 1 . .
H H12 0.6651 1.0025 0.1169 0.022 Uiso calc R 1 . .
C C13 0.6482(2) 0.95202(18) -0.05589(16) 0.0208(4) Uani d . 1 . .
H H13 0.7337 1.0028 -0.0741 0.025 Uiso calc R 1 . .
C C14 0.5635(2) 0.8786(2) -0.14334(16) 0.0223(4) Uani d . 1 . .
H H14 0.5907 0.8795 -0.2214 0.027 Uiso calc R 1 . .
C C15 0.4392(2) 0.8039(2) -0.11654(17) 0.0226(4) Uani d . 1 . .
H H15 0.3806 0.7545 -0.1766 0.027 Uiso calc R 1 . .
C C16 0.4003(2) 0.80114(18) -0.00196(16) 0.0186(4) Uani d . 1 . .
H H16 0.3168 0.7487 0.0163 0.022 Uiso calc R 1 . .
C C21 0.7847(2) 0.59748(18) -0.02063(15) 0.0177(4) Uani d . 1 . .
H H21A 0.6807 0.6274 -0.0689 0.021 Uiso calc R 1 . .
H H21B 0.8044 0.5160 -0.0465 0.021 Uiso calc R 1 . .
C C22 0.7706(2) 0.59932(17) 0.11135(16) 0.0190(4) Uani d . 1 . .
H H22A 0.6525 0.5930 0.1223 0.023 Uiso calc R 1 . .
H H22B 0.8339 0.5330 0.1537 0.023 Uiso calc R 1 . .
C C23 0.9434(2) 0.76919(17) 0.09170(14) 0.0143(3) Uani d . 1 . .
C C25 0.9978(2) 0.91738(17) 0.23010(14) 0.0154(3) Uani d . 1 . .
C C26 0.9012(2) 0.84520(16) 0.30510(15) 0.0143(3) Uani d . 1 . .
C C31 0.89419(19) 0.87809(17) 0.43064(15) 0.0156(3) Uani d . 1 . .
C C32 0.9134(2) 0.78876(18) 0.51682(16) 0.0188(4) Uani d . 1 . .
H H32 0.9285 0.7093 0.4941 0.023 Uiso calc R 1 . .
C C33 0.9105(2) 0.8159(2) 0.63569(17) 0.0235(4) Uani d . 1 . .
H H33 0.9248 0.7553 0.6942 0.028 Uiso calc R 1 . .
C C34 0.8867(2) 0.9319(2) 0.66839(16) 0.0260(4) Uani d . 1 . .
H H34 0.8848 0.9506 0.7495 0.031 Uiso calc R 1 . .
C C35 0.8657(2) 1.0208(2) 0.58350(18) 0.0244(4) Uani d . 1 . .
H H35 0.8481 1.0998 0.6066 0.029 Uiso calc R 1 . .
C C36 0.8704(2) 0.99464(18) 0.46448(17) 0.0194(4) Uani d . 1 . .
H H36 0.8575 1.0558 0.4066 0.023 Uiso calc R 1 . .
N N1 0.47033(17) 0.97927(14) 0.26439(12) 0.0155(3) Uani d . 1 . .
N N2 0.43395(18) 0.98461(14) 0.37602(13) 0.0160(3) Uani d . 1 . .
N N4 0.32664(19) 0.79177(15) 0.37511(13) 0.0189(3) Uani d . 1 . .
N N21 0.82573(17) 0.74777(14) 0.26775(12) 0.0153(3) Uani d . 1 . .
N N22 0.84133(16) 0.71298(14) 0.15618(12) 0.0145(3) Uani d . 1 . .
N N24 1.02182(17) 0.86729(15) 0.12326(13) 0.0160(3) Uani d . 1 . .
O O1 0.33957(18) 0.68178(14) 0.21024(11) 0.0251(3) Uani d . 1 . .
O O2 1.05539(16) 1.01443(12) 0.26137(11) 0.0203(3) Uani d . 1 . .
S S1 0.31134(5) 0.93121(5) 0.56369(4) 0.02183(11) Uani d . 1 . .
S S2 0.96032(5) 0.69245(5) -0.03887(4) 0.01873(10) 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 . . 106.51(12) ?
C2 C1 H1A . . 110.4 ?
S1 C1 H1A . . 110.4 ?
C2 C1 H1B . . 110.4 ?
S1 C1 H1B . . 110.4 ?
H1A C1 H1B . . 108.6 ?
N2 C2 C1 . . 105.22(16) ?
N2 C2 H2A . . 110.7 ?
C1 C2 H2A . . 110.7 ?
N2 C2 H2B . . 110.7 ?
C1 C2 H2B . . 110.7 ?
H2A C2 H2B . . 108.8 ?
N4 C3 N2 . . 125.04(16) ?
N4 C3 S1 . . 122.91(14) ?
N2 C3 S1 . . 112.05(14) ?
O1 C5 N4 . . 120.76(17) ?
O1 C5 C6 . . 122.68(16) ?
N4 C5 C6 . . 116.55(16) ?
N1 C6 C11 . . 115.39(16) ?
N1 C6 C5 . . 122.47(15) ?
C11 C6 C5 . . 122.13(16) ?
C16 C11 C12 . . 118.83(15) ?
C16 C11 C6 . . 121.82(16) ?
C12 C11 C6 . . 119.31(15) ?
C13 C12 C11 . . 120.63(17) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C14 . . 120.07(17) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C15 C14 C13 . . 119.97(16) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 120.26(18) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C15 C16 C11 . . 120.23(17) ?
C15 C16 H16 . . 119.9 ?
C11 C16 H16 . . 119.9 ?
C22 C21 S2 . . 106.82(12) ?
C22 C21 H21A . . 110.4 ?
S2 C21 H21A . . 110.4 ?
C22 C21 H21B . . 110.4 ?
S2 C21 H21B . . 110.4 ?
H21A C21 H21B . . 108.6 ?
N22 C22 C21 . . 105.46(14) ?
N22 C22 H22A . . 110.6 ?
C21 C22 H22A . . 110.6 ?
N22 C22 H22B . . 110.6 ?
C21 C22 H22B . . 110.6 ?
H22A C22 H22B . . 108.8 ?
N24 C23 N22 . . 124.58(15) ?
N24 C23 S2 . . 123.82(13) ?
N22 C23 S2 . . 111.59(13) ?
O2 C25 N24 . . 121.42(15) ?
O2 C25 C26 . . 122.45(15) ?
N24 C25 C26 . . 116.13(16) ?
N21 C26 C31 . . 115.93(15) ?
N21 C26 C25 . . 122.77(15) ?
C31 C26 C25 . . 121.21(15) ?
C36 C31 C32 . . 119.60(16) ?
C36 C31 C26 . . 122.03(16) ?
C32 C31 C26 . . 118.37(17) ?
C33 C32 C31 . . 120.27(19) ?
C33 C32 H32 . . 119.9 ?
C31 C32 H32 . . 119.9 ?
C34 C33 C32 . . 119.69(19) ?
C34 C33 H33 . . 120.2 ?
C32 C33 H33 . . 120.2 ?
C35 C34 C33 . . 120.45(17) ?
C35 C34 H34 . . 119.8 ?
C33 C34 H34 . . 119.8 ?
C34 C35 C36 . . 120.2(2) ?
C34 C35 H35 . . 119.9 ?
C36 C35 H35 . . 119.9 ?
C35 C36 C31 . . 119.73(19) ?
C35 C36 H36 . . 120.1 ?
C31 C36 H36 . . 120.1 ?
C6 N1 N2 . . 116.60(15) ?
C3 N2 N1 . . 122.19(15) ?
C3 N2 C2 . . 117.07(14) ?
N1 N2 C2 . . 119.30(15) ?
C3 N4 C5 . . 117.01(16) ?
C26 N21 N22 . . 116.24(14) ?
C23 N22 N21 . . 122.07(14) ?
C23 N22 C22 . . 117.66(14) ?
N21 N22 C22 . . 119.33(13) ?
C23 N24 C25 . . 117.35(14) ?
C3 S1 C1 . . 91.47(8) ?
C23 S2 C21 . . 91.43(8) ?
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 . 1.530(2) ?
C1 S1 . 1.825(2) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 N2 . 1.463(2) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 N4 . 1.303(2) ?
C3 N2 . 1.347(2) ?
C3 S1 . 1.7436(17) ?
C5 O1 . 1.219(2) ?
C5 N4 . 1.390(2) ?
C5 C6 . 1.493(3) ?
C6 N1 . 1.303(2) ?
C6 C11 . 1.485(2) ?
C11 C16 . 1.401(3) ?
C11 C12 . 1.403(2) ?
C12 C13 . 1.386(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.390(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.389(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.392(3) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C22 . 1.526(2) ?
C21 S2 . 1.8257(18) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 N22 . 1.467(2) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 N24 . 1.302(2) ?
C23 N22 . 1.353(2) ?
C23 S2 . 1.7467(17) ?
C25 O2 . 1.224(2) ?
C25 N24 . 1.385(2) ?
C25 C26 . 1.494(2) ?
C26 N21 . 1.300(2) ?
C26 C31 . 1.487(2) ?
C31 C36 . 1.397(3) ?
C31 C32 . 1.400(3) ?
C32 C33 . 1.392(3) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.388(3) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.386(3) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.394(3) ?
C35 H35 . 0.9500 ?
C36 H36 . 0.9500 ?
N1 N2 . 1.352(2) ?
N21 N22 . 1.3556(19) ?
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
C1 H1B O1 2_656 0.99 2.50 3.183(2) 126
C13 H13 O1 2_655 0.95 2.56 3.150(2) 120
C21 H21B N24 2_745 0.99 2.45 3.351(2) 151
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 N2 . . . . -28.20(17) ?
O1 C5 C6 N1 . . . . -178.65(16) ?
N4 C5 C6 N1 . . . . 0.7(2) ?
O1 C5 C6 C11 . . . . 2.0(3) ?
N4 C5 C6 C11 . . . . -178.61(15) ?
N1 C6 C11 C16 . . . . -152.22(17) ?
C5 C6 C11 C16 . . . . 27.2(2) ?
N1 C6 C11 C12 . . . . 25.5(2) ?
C5 C6 C11 C12 . . . . -155.16(16) ?
C16 C11 C12 C13 . . . . -0.4(3) ?
C6 C11 C12 C13 . . . . -178.19(16) ?
C11 C12 C13 C14 . . . . 1.0(3) ?
C12 C13 C14 C15 . . . . -0.4(3) ?
C13 C14 C15 C16 . . . . -0.8(3) ?
C14 C15 C16 C11 . . . . 1.3(3) ?
C12 C11 C16 C15 . . . . -0.7(3) ?
C6 C11 C16 C15 . . . . 176.98(17) ?
S2 C21 C22 N22 . . . . 26.76(16) ?
O2 C25 C26 N21 . . . . 172.98(16) ?
N24 C25 C26 N21 . . . . -8.2(2) ?
O2 C25 C26 C31 . . . . -10.5(3) ?
N24 C25 C26 C31 . . . . 168.27(14) ?
N21 C26 C31 C36 . . . . -139.66(17) ?
C25 C26 C31 C36 . . . . 43.6(2) ?
N21 C26 C31 C32 . . . . 40.8(2) ?
C25 C26 C31 C32 . . . . -135.91(17) ?
C36 C31 C32 C33 . . . . -0.6(3) ?
C26 C31 C32 C33 . . . . 178.92(16) ?
C31 C32 C33 C34 . . . . 0.7(3) ?
C32 C33 C34 C35 . . . . 0.0(3) ?
C33 C34 C35 C36 . . . . -0.8(3) ?
C34 C35 C36 C31 . . . . 0.8(3) ?
C32 C31 C36 C35 . . . . -0.1(3) ?
C26 C31 C36 C35 . . . . -179.65(15) ?
C11 C6 N1 N2 . . . . -179.08(13) ?
C5 C6 N1 N2 . . . . 1.5(2) ?
N4 C3 N2 N1 . . . . 4.5(3) ?
S1 C3 N2 N1 . . . . -174.42(12) ?
N4 C3 N2 C2 . . . . 170.77(16) ?
S1 C3 N2 C2 . . . . -8.2(2) ?
C6 N1 N2 C3 . . . . -4.1(2) ?
C6 N1 N2 C2 . . . . -170.01(16) ?
C1 C2 N2 C3 . . . . 24.4(2) ?
C1 C2 N2 N1 . . . . -168.96(14) ?
N2 C3 N4 C5 . . . . -1.9(3) ?
S1 C3 N4 C5 . . . . 176.91(13) ?
O1 C5 N4 C3 . . . . 178.81(17) ?
C6 C5 N4 C3 . . . . -0.6(2) ?
C31 C26 N21 N22 . . . . -175.59(14) ?
C25 C26 N21 N22 . . . . 1.1(2) ?
N24 C23 N22 N21 . . . . -7.5(3) ?
S2 C23 N22 N21 . . . . 171.45(12) ?
N24 C23 N22 C22 . . . . -176.32(16) ?
S2 C23 N22 C22 . . . . 2.63(19) ?
C26 N21 N22 C23 . . . . 6.7(2) ?
C26 N21 N22 C22 . . . . 175.30(15) ?
C21 C22 N22 C23 . . . . -19.9(2) ?
C21 C22 N22 N21 . . . . 170.99(14) ?
N22 C23 N24 C25 . . . . -0.4(2) ?
S2 C23 N24 C25 . . . . -179.20(13) ?
O2 C25 N24 C23 . . . . -173.69(16) ?
C26 C25 N24 C23 . . . . 7.5(2) ?
N4 C3 S1 C1 . . . . 172.19(15) ?
N2 C3 S1 C1 . . . . -8.81(14) ?
C2 C1 S1 C3 . . . . 21.75(13) ?
N24 C23 S2 C21 . . . . -168.58(15) ?
N22 C23 S2 C21 . . . . 12.46(14) ?
C22 C21 S2 C23 . . . . -22.94(14) ?
