#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/11/2211184.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_2211184
loop_
_publ_author_name
'Li-Xue Zhang'
'San-Nu Zhou'
'Jian-Yu Jin'
'Hong-Ping Xiao'
'An-Jiang Zhang'
_publ_section_title
6-(2,4-Difluorophenyl)-3-(4-methylphenyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine
_journal_coeditor_code           SF2004
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5018
_journal_page_last               o5019
_journal_paper_doi               10.1107/S1600536806040438
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H12 F2 N4 S'
_chemical_formula_moiety         'C17 H12 F2 N4 S'
_chemical_formula_sum            'C17 H12 F2 N4 S'
_chemical_formula_weight         342.37
_chemical_name_systematic
;
 6-(2,4-Difluorophenyl)-3-(4-methylphenyl)-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                 109.827(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0693(11)
_cell_length_b                   13.0368(12)
_cell_length_c                   10.4572(9)
_cell_measurement_reflns_used    2240
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.68
_cell_measurement_theta_min      2.74
_cell_volume                     1547.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8050
_diffrn_reflns_theta_full        25.23
_diffrn_reflns_theta_max         25.23
_diffrn_reflns_theta_min         1.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.9516
_exptl_absorpt_correction_T_min  0.9126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.233
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0486
_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)+(0.0636P)²+0.4070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                2269
_reflns_number_total             2787
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf2004.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211184
_cod_database_fobs_code          2211184
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
S S1 1.03481(5) 0.80444(5) 1.24396(6) 0.0478(2) Uani d . 1
F F1 0.73830(14) 0.76724(11) 0.70989(14) 0.0620(4) Uani d . 1
F F2 0.62307(17) 0.42587(13) 0.68514(18) 0.0886(6) Uani d . 1
N N1 0.82516(16) 0.83920(14) 0.96963(17) 0.0387(4) Uani d . 1
N N2 0.88603(15) 0.92174(13) 1.04622(18) 0.0381(4) Uani d . 1
N N3 0.99200(18) 1.01110(16) 1.2232(2) 0.0518(5) Uani d . 1
N N4 0.91361(18) 1.07673(15) 1.1313(2) 0.0513(5) Uani d . 1
C C1 0.7436(2) 0.67609(17) 0.7725(2) 0.0426(5) Uani d . 1
C C2 0.6799(2) 0.5973(2) 0.6968(3) 0.0524(6) Uani d . 1
H H2 0.6334 0.6067 0.6063 0.063 Uiso calc R 1
C C3 0.6871(2) 0.5040(2) 0.7590(3) 0.0555(7) Uani d . 1
C C4 0.7562(2) 0.4874(2) 0.8911(3) 0.0593(7) Uani d . 1
H H4 0.7601 0.4229 0.9304 0.071 Uiso calc R 1
C C5 0.8201(2) 0.56838(18) 0.9645(2) 0.0495(6) Uani d . 1
H H5 0.8680 0.5578 1.0541 0.059 Uiso calc R 1
C C6 0.81474(19) 0.66567(17) 0.9079(2) 0.0379(5) Uani d . 1
C C7 0.87967(19) 0.75313(17) 0.9893(2) 0.0374(5) Uani d . 1
C C8 1.0043(2) 0.73736(18) 1.0841(2) 0.0438(6) Uani d . 1
H H8A 1.0585 0.7611 1.0400 0.053 Uiso calc R 1
H H8B 1.0179 0.6646 1.1020 0.053 Uiso calc R 1
C C9 0.97367(19) 0.91937(18) 1.1708(2) 0.0419(5) Uani d . 1
C C10 0.84938(19) 1.02217(17) 1.0271(2) 0.0401(5) Uani d . 1
C C11 0.75565(19) 1.06402(17) 0.9093(2) 0.0411(5) Uani d . 1
C C12 0.7039(2) 1.15618(18) 0.9252(3) 0.0497(6) Uani d . 1
H H12 0.7277 1.1887 1.0093 0.060 Uiso calc R 1
C C13 0.6174(2) 1.1993(2) 0.8164(3) 0.0551(7) Uani d . 1
H H13 0.5839 1.2612 0.8284 0.066 Uiso calc R 1
C C14 0.5789(2) 1.1535(2) 0.6901(3) 0.0500(6) Uani d . 1
C C15 0.6317(2) 1.0620(2) 0.6756(3) 0.0565(7) Uani d . 1
H H15 0.6076 1.0297 0.5913 0.068 Uiso calc R 1
C C16 0.7186(2) 1.01748(19) 0.7823(2) 0.0506(6) Uani d . 1
H H16 0.7527 0.9561 0.7695 0.061 Uiso calc R 1
C C17 0.4837(2) 1.2022(2) 0.5724(3) 0.0687(8) Uani d . 1
H H17A 0.5174 1.2552 0.5335 0.103 Uiso calc R 1
H H17B 0.4247 1.2312 0.6042 0.103 Uiso calc R 1
H H17C 0.4485 1.1510 0.5048 0.103 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'
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
_geom_angle_publ_flag
C9 S1 C8 95.00(10) yes
C7 N1 N2 116.25(17) ?
C9 N2 C10 105.44(18) yes
C9 N2 N1 127.95(18) yes
C10 N2 N1 124.83(17) yes
C9 N3 N4 107.16(18) ?
C10 N4 N3 108.21(18) yes
F1 C1 C2 117.2(2) ?
F1 C1 C6 119.4(2) ?
C2 C1 C6 123.3(2) ?
C1 C2 C3 117.5(2) ?
C1 C2 H2 121.3 ?
C3 C2 H2 121.3 ?
F2 C3 C4 119.5(2) ?
F2 C3 C2 117.9(2) ?
C4 C3 C2 122.6(2) ?
C3 C4 C5 118.4(2) ?
C3 C4 H4 120.8 ?
C5 C4 H4 120.8 ?
C4 C5 C6 121.7(2) ?
C4 C5 H5 119.1 ?
C6 C5 H5 119.1 ?
C5 C6 C1 116.4(2) ?
C5 C6 C7 121.3(2) ?
C1 C6 C7 122.3(2) ?
N1 C7 C6 116.10(19) ?
N1 C7 C8 124.6(2) ?
C6 C7 C8 119.27(19) ?
C7 C8 S1 112.75(16) ?
C7 C8 H8A 109.0 ?
S1 C8 H8A 109.0 ?
C7 C8 H8B 109.0 ?
S1 C8 H8B 109.0 ?
H8A C8 H8B 107.8 ?
N3 C9 N2 110.2(2) yes
N3 C9 S1 128.51(17) yes
N2 C9 S1 121.03(17) yes
N4 C10 N2 108.96(19) yes
N4 C10 C11 124.5(2) ?
N2 C10 C11 126.5(2) ?
C16 C11 C12 118.7(2) ?
C16 C11 C10 123.2(2) ?
C12 C11 C10 118.1(2) ?
C13 C12 C11 120.0(2) ?
C13 C12 H12 120.0 ?
C11 C12 H12 120.0 ?
C12 C13 C14 122.0(2) ?
C12 C13 H13 119.0 ?
C14 C13 H13 119.0 ?
C13 C14 C15 117.4(2) ?
C13 C14 C17 121.0(2) ?
C15 C14 C17 121.6(3) ?
C16 C15 C14 121.8(2) ?
C16 C15 H15 119.1 ?
C14 C15 H15 119.1 ?
C15 C16 C11 120.1(2) ?
C15 C16 H16 119.9 ?
C11 C16 H16 119.9 ?
C14 C17 H17A 109.5 ?
C14 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C14 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C9 1.730(2) yes
S1 C8 1.810(2) yes
F1 C1 1.348(3) ?
F2 C3 1.351(3) ?
N1 C7 1.282(3) yes
N1 N2 1.393(2) yes
N2 C9 1.372(3) yes
N2 C10 1.375(3) yes
N3 C9 1.303(3) yes
N3 N4 1.391(3) yes
N4 C10 1.312(3) yes
C1 C2 1.363(3) ?
C1 C6 1.392(3) ?
C2 C3 1.368(4) ?
C2 H2 0.9300 ?
C3 C4 1.368(4) ?
C4 C5 1.377(3) ?
C4 H4 0.9300 ?
C5 C6 1.391(3) ?
C5 H5 0.9300 ?
C6 C7 1.478(3) ?
C7 C8 1.509(3) yes
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C10 C11 1.466(3) ?
C11 C16 1.389(3) ?
C11 C12 1.390(3) ?
C12 C13 1.376(3) ?
C12 H12 0.9300 ?
C13 C14 1.378(4) ?
C13 H13 0.9300 ?
C14 C15 1.385(4) ?
C14 C17 1.509(3) ?
C15 C16 1.374(3) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
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
_geom_torsion_publ_flag
C7 N1 N2 C9 -26.6(3) yes
C7 N1 N2 C10 170.9(2) yes
C9 N3 N4 C10 0.8(3) yes
F1 C1 C2 C3 178.5(2) ?
C6 C1 C2 C3 0.3(4) ?
C1 C2 C3 F2 179.2(2) ?
C1 C2 C3 C4 -1.2(4) ?
F2 C3 C4 C5 -179.6(2) ?
C2 C3 C4 C5 0.7(4) ?
C3 C4 C5 C6 0.6(4) ?
C4 C5 C6 C1 -1.4(4) ?
C4 C5 C6 C7 177.4(2) ?
F1 C1 C6 C5 -177.3(2) ?
C2 C1 C6 C5 1.0(4) ?
F1 C1 C6 C7 4.0(3) ?
C2 C1 C6 C7 -177.8(2) ?
N2 N1 C7 C6 179.92(18) yes
N2 N1 C7 C8 -2.3(3) yes
C5 C6 C7 N1 -139.7(2) ?
C1 C6 C7 N1 39.1(3) ?
C5 C6 C7 C8 42.5(3) ?
C1 C6 C7 C8 -138.8(2) ?
N1 C7 C8 S1 42.2(3) yes
C6 C7 C8 S1 -140.07(18) ?
C9 S1 C8 C7 -47.28(18) yes
N4 N3 C9 N2 0.4(3) yes
N4 N3 C9 S1 -173.65(18) yes
C10 N2 C9 N3 -1.4(3) yes
N1 N2 C9 N3 -166.6(2) yes
C10 N2 C9 S1 173.14(17) yes
N1 N2 C9 S1 7.9(3) yes
C8 S1 C9 N3 -159.5(2) yes
C8 S1 C9 N2 27.0(2) yes
N3 N4 C10 N2 -1.8(3) yes
N3 N4 C10 C11 179.3(2) ?
C9 N2 C10 N4 2.0(2) ?
N1 N2 C10 N4 167.7(2) ?
C9 N2 C10 C11 -179.1(2) ?
N1 N2 C10 C11 -13.3(4) ?
N4 C10 C11 C16 155.8(2) ?
N2 C10 C11 C16 -23.0(4) ?
N4 C10 C11 C12 -22.4(4) ?
N2 C10 C11 C12 158.8(2) ?
C16 C11 C12 C13 0.3(4) ?
C10 C11 C12 C13 178.6(2) ?
C11 C12 C13 C14 0.3(4) ?
C12 C13 C14 C15 -0.6(4) ?
C12 C13 C14 C17 179.8(2) ?
C13 C14 C15 C16 0.3(4) ?
C17 C14 C15 C16 179.8(2) ?
C14 C15 C16 C11 0.3(4) ?
C12 C11 C16 C15 -0.6(4) ?
C10 C11 C16 C15 -178.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126100
