#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/94/2239414.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_2239414
loop_
_publ_author_name
'Palakshamurthy, B. S.'
'Devarajegowda, H. C.'
'Mohan, N. R.'
'Sreenivasa, S.'
'Suchetan, P. A.'
_publ_section_title
;
 6-(4-Fluorophenyl)-3-phenyl-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine
;
_journal_coeditor_code           HB7198
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o375
_journal_paper_doi               10.1107/S1600536814003262
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C16 H11 F N4 S'
_chemical_formula_moiety         'C16 H11 F N4 S'
_chemical_formula_sum            'C16 H11 F N4 S'
_chemical_formula_weight         310.35
_chemical_melting_point          523
_chemical_name_systematic
6-(4-Fluorophenyl)-3-phenyl-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.076(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.088(2)
_cell_length_b                   13.464(2)
_cell_length_c                   7.0557(12)
_cell_measurement_reflns_used    199
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      1.2
_cell_volume                     1433.1(4)
_computing_cell_refinement       'APEX2 and SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2009)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and
Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 1.6
_diffrn_measured_fraction_theta_full 0.763
_diffrn_measured_fraction_theta_max 0.763
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi 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  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9962
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        1.3
_diffrn_standards_interval_count 23
_diffrn_standards_interval_time  22
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.9584
_exptl_absorpt_correction_T_min  0.9385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    11
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0688P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                1630
_reflns_number_total             2154
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7198sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1433.0(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239414
_cod_database_fobs_code          2239414
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_symmetry_multiplicity
S S1 1.01380(5) 0.90521(5) 0.19233(12) 0.0434(2) Uani d . 1 1
N N3 0.86107(14) 0.80121(14) 0.1963(3) 0.0328(5) Uani d . 1 1
N N2 0.97880(15) 0.70583(16) 0.2103(4) 0.0444(6) Uani d . 1 1
N N1 0.90331(15) 0.64596(17) 0.2066(4) 0.0416(6) Uani d . 1 1
N N4 0.80738(14) 0.88156(15) 0.1519(3) 0.0330(5) Uani d . 1 1
C C10 0.83938(16) 0.96827(18) 0.1890(4) 0.0321(6) Uani d . 1 1
C C7 0.83399(17) 0.70319(18) 0.1968(4) 0.0340(6) Uani d . 1 1
C C6 0.74169(17) 0.66820(19) 0.1859(4) 0.0351(6) Uani d . 1 1
C C9 0.92724(16) 0.9844(2) 0.2857(4) 0.0391(6) Uani d . 1 1
H H9A 0.9215 0.9715 0.4202 0.047 Uiso calc R 1 1
H H9B 0.9444 1.0533 0.2709 0.047 Uiso calc R 1 1
C C11 0.78112(17) 1.05326(18) 0.1437(4) 0.0343(6) Uani d . 1 1
C C8 0.95214(16) 0.79732(19) 0.2038(4) 0.0357(6) Uani d . 1 1
F F1 0.61197(13) 1.28437(13) 0.0296(4) 0.0784(7) Uani d . 1 1
C C5 0.7266(2) 0.5726(2) 0.1183(4) 0.0450(7) Uani d . 1 1
H H5 0.7739 0.5326 0.0841 0.054 Uiso calc R 1 1
C C15 0.6392(2) 1.1137(2) 0.0357(5) 0.0543(8) Uani d . 1 1
H H15 0.5822 1.1019 -0.0114 0.065 Uiso calc R 1 1
C C1 0.67026(18) 0.7263(2) 0.2400(5) 0.0432(7) Uani d . 1 1
H H1 0.6800 0.7897 0.2881 0.052 Uiso calc R 1 1
C C16 0.69570(18) 1.0365(2) 0.0751(5) 0.0458(7) Uani d . 1 1
H H16 0.6764 0.9716 0.0556 0.055 Uiso calc R 1 1
C C2 0.5845(2) 0.6898(2) 0.2223(6) 0.0571(9) Uani d . 1 1
H H2 0.5366 0.7289 0.2570 0.068 Uiso calc R 1 1
C C12 0.80794(19) 1.1509(2) 0.1700(5) 0.0473(7) Uani d . 1 1
H H12 0.8653 1.1640 0.2139 0.057 Uiso calc R 1 1
C C3 0.5708(2) 0.5959(2) 0.1535(6) 0.0597(9) Uani d . 1 1
H H3 0.5133 0.5714 0.1412 0.072 Uiso calc R 1 1
C C14 0.6683(2) 1.2082(2) 0.0669(5) 0.0510(8) Uani d . 1 1
C C13 0.7514(2) 1.2285(2) 0.1325(6) 0.0559(9) Uani d . 1 1
H H13 0.7697 1.2938 0.1517 0.067 Uiso calc R 1 1
C C4 0.6409(2) 0.5377(2) 0.1024(5) 0.0583(9) Uani d . 1 1
H H4 0.6306 0.4739 0.0566 0.070 Uiso calc R 1 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'
F F 0.0171 0.0103 '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
C8 S1 C9 94.87(13)
C8 N3 C7 105.0(2)
C8 N3 N4 128.2(2)
C7 N3 N4 125.1(2)
C8 N2 N1 107.2(2)
C7 N1 N2 108.3(2)
C10 N4 N3 116.5(2)
N4 C10 C11 116.1(2)
N4 C10 C9 123.4(2)
C11 C10 C9 120.4(2)
N1 C7 N3 109.2(2)
N1 C7 C6 125.0(2)
N3 C7 C6 125.8(2)
C1 C6 C5 119.5(3)
C1 C6 C7 122.9(2)
C5 C6 C7 117.6(2)
C10 C9 S1 112.70(19)
C10 C9 H9A 109.1
S1 C9 H9A 109.1
C10 C9 H9B 109.1
S1 C9 H9B 109.1
H9A C9 H9B 107.8
C16 C11 C12 117.9(3)
C16 C11 C10 119.7(2)
C12 C11 C10 122.4(2)
N2 C8 N3 110.3(2)
N2 C8 S1 129.3(2)
N3 C8 S1 120.31(19)
C4 C5 C6 119.4(3)
C4 C5 H5 120.3
C6 C5 H5 120.3
C14 C15 C16 118.6(3)
C14 C15 H15 120.7
C16 C15 H15 120.7
C6 C1 C2 120.2(3)
C6 C1 H1 119.9
C2 C1 H1 119.9
C15 C16 C11 121.2(3)
C15 C16 H16 119.4
C11 C16 H16 119.4
C3 C2 C1 119.6(3)
C3 C2 H2 120.2
C1 C2 H2 120.2
C13 C12 C11 121.1(3)
C13 C12 H12 119.4
C11 C12 H12 119.4
C2 C3 C4 120.6(3)
C2 C3 H3 119.7
C4 C3 H3 119.7
F1 C14 C13 119.1(3)
F1 C14 C15 118.5(3)
C13 C14 C15 122.4(3)
C14 C13 C12 118.7(3)
C14 C13 H13 120.6
C12 C13 H13 120.6
C3 C4 C5 120.7(3)
C3 C4 H4 119.6
C5 C4 H4 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.728(3)
S1 C9 1.819(3)
N3 C8 1.375(3)
N3 C7 1.382(3)
N3 N4 1.384(3)
N2 C8 1.296(3)
N2 N1 1.395(3)
N1 C7 1.300(3)
N4 C10 1.288(3)
C10 C11 1.474(3)
C10 C9 1.495(3)
C7 C6 1.471(4)
C6 C1 1.391(4)
C6 C5 1.390(4)
C9 H9A 0.9700
C9 H9B 0.9700
C11 C16 1.387(4)
C11 C12 1.387(4)
F1 C14 1.354(3)
C5 C4 1.378(4)
C5 H5 0.9300
C15 C14 1.362(4)
C15 C16 1.370(4)
C15 H15 0.9300
C1 C2 1.388(4)
C1 H1 0.9300
C16 H16 0.9300
C2 C3 1.369(4)
C2 H2 0.9300
C12 C13 1.371(4)
C12 H12 0.9300
C3 C4 1.371(5)
C3 H3 0.9300
C14 C13 1.356(5)
C13 H13 0.9300
C4 H4 0.9300
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
C9 H9B N2 2_755 0.97 2.36 3.301(3) 164
C12 H12 N2 2_755 0.93 2.47 3.393(4) 173
C4 H4 F1 1_545 0.93 2.57 3.475(4) 164
C1 H1 Cg3 4_576 0.93 2.93 3.598(3) 130
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
C8 N2 N1 C7 0.4(3)
C8 N3 N4 C10 -28.0(4)
C7 N3 N4 C10 168.8(2)
N3 N4 C10 C11 -179.2(2)
N3 N4 C10 C9 -3.7(4)
N2 N1 C7 N3 -0.8(3)
N2 N1 C7 C6 178.6(3)
C8 N3 C7 N1 0.9(3)
N4 N3 C7 N1 167.3(2)
C8 N3 C7 C6 -178.5(3)
N4 N3 C7 C6 -12.1(4)
N1 C7 C6 C1 157.2(3)
N3 C7 C6 C1 -23.5(4)
N1 C7 C6 C5 -22.7(4)
N3 C7 C6 C5 156.5(3)
N4 C10 C9 S1 44.7(3)
C11 C10 C9 S1 -140.1(2)
C8 S1 C9 C10 -48.7(2)
N4 C10 C11 C16 3.3(4)
C9 C10 C11 C16 -172.2(3)
N4 C10 C11 C12 -177.8(3)
C9 C10 C11 C12 6.7(4)
N1 N2 C8 N3 0.1(3)
N1 N2 C8 S1 -176.5(2)
C7 N3 C8 N2 -0.6(3)
N4 N3 C8 N2 -166.4(3)
C7 N3 C8 S1 176.35(19)
N4 N3 C8 S1 10.5(4)
C9 S1 C8 N2 -158.0(3)
C9 S1 C8 N3 25.7(2)
C1 C6 C5 C4 1.3(5)
C7 C6 C5 C4 -178.8(3)
C5 C6 C1 C2 -1.5(5)
C7 C6 C1 C2 178.6(3)
C14 C15 C16 C11 -0.6(5)
C12 C11 C16 C15 -0.4(5)
C10 C11 C16 C15 178.5(3)
C6 C1 C2 C3 0.8(5)
C16 C11 C12 C13 1.1(5)
C10 C11 C12 C13 -177.9(3)
C1 C2 C3 C4 0.2(6)
C16 C15 C14 F1 -179.3(3)
C16 C15 C14 C13 1.1(6)
F1 C14 C13 C12 180.0(3)
C15 C14 C13 C12 -0.5(6)
C11 C12 C13 C14 -0.6(5)
C2 C3 C4 C5 -0.4(6)
C6 C5 C4 C3 -0.4(5)
