#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229946.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_2229946
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Asik, Safra Izuani Jama'
'Razak, Ibrahim Abdul'
Nithinchandra
'Kalluraya, Balakrishna'
_publ_section_title
;
 7-(4-Chlorobenzylidene)-3-[(4-chlorophenoxy)methyl]-6-(4-nitrothiophen-2-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine
;
_journal_coeditor_code           CI5185
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1266
_journal_page_last               o1267
_journal_paper_doi               10.1107/S1600536811015637
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H13 Cl2 N5 O3 S2'
_chemical_formula_moiety         'C22 H13 Cl2 N5 O3 S2'
_chemical_formula_sum            'C22 H13 Cl2 N5 O3 S2'
_chemical_formula_weight         530.39
_chemical_name_systematic
;
7-(4-Chlorobenzylidene)-3-[(4-chlorophenoxy)methyl]-6-(4-nitrothiophen-2-yl)-
7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.4340(10)
_cell_angle_beta                 97.9810(10)
_cell_angle_gamma                109.2420(10)
_cell_formula_units_Z            2
_cell_length_a                   8.5021(2)
_cell_length_b                   10.0379(2)
_cell_length_c                   14.3623(3)
_cell_measurement_reflns_used    5767
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.95
_cell_measurement_theta_min      2.74
_cell_volume                     1136.07(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Bruker SMART APEXII 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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19590
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_T_max  0.9455
_exptl_absorpt_correction_T_min  0.8266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0647P)²+0.3979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1333
_reflns_number_gt                5142
_reflns_number_total             6548
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5185.cif
_cod_data_source_block           I
_cod_database_code               2229946
_cod_database_fobs_code          2229946
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.31310(6) 0.39243(5) 0.13806(3) 0.03764(12) Uani d . 1 1 . .
S S2 0.65367(7) 0.90408(5) 0.02701(4) 0.04462(14) Uani d . 1 1 . .
Cl Cl1 0.32206(12) 1.05741(9) -0.46034(7) 0.0906(3) Uani d . 1 1 . .
Cl Cl2 0.17004(8) 0.36669(8) 0.58962(4) 0.06035(17) Uani d . 1 1 . .
N N1 0.0052(2) 0.34827(18) -0.09684(11) 0.0418(4) Uani d . 1 1 . .
N N2 0.0543(2) 0.29741(17) -0.01333(11) 0.0391(3) Uani d . 1 1 . .
N N3 0.23458(18) 0.51207(16) -0.01635(10) 0.0316(3) Uani d . 1 1 . .
N N4 0.37735(19) 0.63329(16) 0.00403(10) 0.0349(3) Uani d . 1 1 . .
N N5 1.0471(2) 0.9832(2) 0.22741(17) 0.0602(5) Uani d . 1 1 . .
O O1 0.25195(18) 0.62527(17) -0.20276(10) 0.0451(3) Uani d . 1 1 . .
O O2 1.1570(3) 1.0856(3) 0.2079(2) 0.0994(8) Uani d . 1 1 . .
O O3 1.0661(3) 0.9215(3) 0.29489(15) 0.0825(6) Uani d . 1 1 . .
C C1 0.1175(3) 0.7481(2) -0.31056(13) 0.0416(4) Uani d . 1 1 . .
H H1A 0.0097 0.6926 -0.3027 0.050 Uiso calc R 1 1 . .
C C2 0.1376(3) 0.8504(2) -0.37127(14) 0.0455(5) Uani d . 1 1 . .
H H2A 0.0436 0.8644 -0.4045 0.055 Uiso calc R 1 1 . .
C C3 0.2982(3) 0.9316(2) -0.38211(16) 0.0486(5) Uani d . 1 1 . .
C C4 0.4404(3) 0.9153(3) -0.33232(18) 0.0540(5) Uani d . 1 1 . .
H H4A 0.5479 0.9717 -0.3399 0.065 Uiso calc R 1 1 . .
C C5 0.4199(3) 0.8139(2) -0.27120(15) 0.0464(5) Uani d . 1 1 . .
H H5A 0.5145 0.8028 -0.2364 0.056 Uiso calc R 1 1 . .
C C6 0.2593(2) 0.7284(2) -0.26134(12) 0.0367(4) Uani d . 1 1 . .
C C7 0.0975(3) 0.5693(2) -0.16998(14) 0.0433(4) Uani d . 1 1 . .
H H7A 0.0089 0.5158 -0.2227 0.052 Uiso calc R 1 1 . .
H H7B 0.0664 0.6464 -0.1426 0.052 Uiso calc R 1 1 . .
C C8 0.1140(2) 0.4746(2) -0.09737(12) 0.0355(4) Uani d . 1 1 . .
C C9 0.1912(2) 0.39706(18) 0.03185(12) 0.0321(3) Uani d . 1 1 . .
C C10 0.4010(2) 0.57962(18) 0.16945(12) 0.0314(3) Uani d . 1 1 . .
C C11 0.4557(2) 0.66196(18) 0.09118(12) 0.0317(3) Uani d . 1 1 . .
C C12 0.6138(2) 0.78458(19) 0.10904(12) 0.0336(3) Uani d . 1 1 . .
C C13 0.7497(2) 0.8140(2) 0.17988(13) 0.0379(4) Uani d . 1 1 . .
H H13A 0.7535 0.7623 0.2307 0.045 Uiso calc R 1 1 . .
C C14 0.8840(2) 0.9339(2) 0.16526(15) 0.0416(4) Uani d . 1 1 . .
C C15 0.8518(3) 0.9942(2) 0.08699(16) 0.0456(5) Uani d . 1 1 . .
H H15A 0.9278 1.0739 0.0687 0.055 Uiso calc R 1 1 . .
C C16 0.4132(2) 0.64263(19) 0.25710(12) 0.0351(4) Uani d . 1 1 . .
H H16A 0.4627 0.7413 0.2673 0.042 Uiso calc R 1 1 . .
C C17 0.3573(2) 0.57331(19) 0.33897(12) 0.0336(3) Uani d . 1 1 . .
C C18 0.2834(3) 0.6385(2) 0.40089(13) 0.0405(4) Uani d . 1 1 . .
H H18A 0.2732 0.7258 0.3906 0.049 Uiso calc R 1 1 . .
C C19 0.2251(3) 0.5746(2) 0.47743(13) 0.0435(4) Uani d . 1 1 . .
H H19A 0.1746 0.6180 0.5179 0.052 Uiso calc R 1 1 . .
C C20 0.2426(2) 0.4462(2) 0.49313(12) 0.0392(4) Uani d . 1 1 . .
C C21 0.3189(3) 0.3808(2) 0.43452(13) 0.0411(4) Uani d . 1 1 . .
H H21A 0.3314 0.2947 0.4463 0.049 Uiso calc R 1 1 . .
C C22 0.3765(2) 0.4453(2) 0.35809(12) 0.0377(4) Uani d . 1 1 . .
H H22A 0.4290 0.4021 0.3188 0.045 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'
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'
Cl Cl 0.1484 0.1585 '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
C9 S1 C10 . . 95.62(8) ?
C15 S2 C12 . . 92.18(10) ?
C8 N1 N2 . . 107.87(15) ?
C9 N2 N1 . . 106.29(15) ?
C9 N3 C8 . . 104.63(14) ?
C9 N3 N4 . . 128.75(14) ?
C8 N3 N4 . . 126.23(14) ?
C11 N4 N3 . . 115.80(14) ?
O3 N5 O2 . . 124.2(2) ?
O3 N5 C14 . . 118.5(2) ?
O2 N5 C14 . . 117.2(2) ?
C6 O1 C7 . . 115.44(15) ?
C2 C1 C6 . . 119.61(19) ?
C2 C1 H1A . . 120.2 ?
C6 C1 H1A . . 120.2 ?
C3 C2 C1 . . 119.4(2) ?
C3 C2 H2A . . 120.3 ?
C1 C2 H2A . . 120.3 ?
C2 C3 C4 . . 121.7(2) ?
C2 C3 Cl1 . . 119.05(18) ?
C4 C3 Cl1 . . 119.29(18) ?
C5 C4 C3 . . 118.8(2) ?
C5 C4 H4A . . 120.6 ?
C3 C4 H4A . . 120.6 ?
C4 C5 C6 . . 120.4(2) ?
C4 C5 H5A . . 119.8 ?
C6 C5 H5A . . 119.8 ?
O1 C6 C5 . . 116.08(17) ?
O1 C6 C1 . . 123.84(17) ?
C5 C6 C1 . . 120.07(18) ?
O1 C7 C8 . . 109.98(16) ?
O1 C7 H7A . . 109.7 ?
C8 C7 H7A . . 109.7 ?
O1 C7 H7B . . 109.7 ?
C8 C7 H7B . . 109.7 ?
H7A C7 H7B . . 108.2 ?
N1 C8 N3 . . 109.93(16) ?
N1 C8 C7 . . 124.21(17) ?
N3 C8 C7 . . 125.52(17) ?
N2 C9 N3 . . 111.26(15) ?
N2 C9 S1 . . 127.32(14) ?
N3 C9 S1 . . 121.40(13) ?
C16 C10 C11 . . 122.26(16) ?
C16 C10 S1 . . 122.39(13) ?
C11 C10 S1 . . 115.32(12) ?
N4 C11 C12 . . 114.57(15) ?
N4 C11 C10 . . 125.55(16) ?
C12 C11 C10 . . 119.85(15) ?
C13 C12 C11 . . 128.47(16) ?
C13 C12 S2 . . 111.57(14) ?
C11 C12 S2 . . 119.62(13) ?
C12 C13 C14 . . 110.48(17) ?
C12 C13 H13A . . 124.8 ?
C14 C13 H13A . . 124.8 ?
C15 C14 C13 . . 115.29(18) ?
C15 C14 N5 . . 122.83(19) ?
C13 C14 N5 . . 121.8(2) ?
C14 C15 S2 . . 110.47(15) ?
C14 C15 H15A . . 124.8 ?
S2 C15 H15A . . 124.8 ?
C10 C16 C17 . . 127.24(17) ?
C10 C16 H16A . . 116.4 ?
C17 C16 H16A . . 116.4 ?
C22 C17 C18 . . 118.34(16) ?
C22 C17 C16 . . 122.56(16) ?
C18 C17 C16 . . 119.10(17) ?
C19 C18 C17 . . 120.80(18) ?
C19 C18 H18A . . 119.6 ?
C17 C18 H18A . . 119.6 ?
C20 C19 C18 . . 119.36(18) ?
C20 C19 H19A . . 120.3 ?
C18 C19 H19A . . 120.3 ?
C19 C20 C21 . . 121.20(17) ?
C19 C20 Cl2 . . 119.24(15) ?
C21 C20 Cl2 . . 119.55(16) ?
C20 C21 C22 . . 119.05(18) ?
C20 C21 H21A . . 120.5 ?
C22 C21 H21A . . 120.5 ?
C21 C22 C17 . . 121.21(17) ?
C21 C22 H22A . . 119.4 ?
C17 C22 H22A . . 119.4 ?
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
S1 C9 . 1.7342(18) ?
S1 C10 . 1.7727(18) ?
S2 C15 . 1.694(2) ?
S2 C12 . 1.7330(17) ?
Cl1 C3 . 1.736(2) ?
Cl2 C20 . 1.7386(18) ?
N1 C8 . 1.302(2) ?
N1 N2 . 1.403(2) ?
N2 C9 . 1.303(2) ?
N3 C9 . 1.364(2) ?
N3 C8 . 1.376(2) ?
N3 N4 . 1.383(2) ?
N4 C11 . 1.296(2) ?
N5 O3 . 1.210(3) ?
N5 O2 . 1.221(3) ?
N5 C14 . 1.449(3) ?
O1 C6 . 1.375(2) ?
O1 C7 . 1.410(2) ?
C1 C2 . 1.382(3) ?
C1 C6 . 1.391(3) ?
C1 H1A . 0.93 ?
C2 C3 . 1.378(3) ?
C2 H2A . 0.93 ?
C3 C4 . 1.381(3) ?
C4 C5 . 1.378(3) ?
C4 H4A . 0.93 ?
C5 C6 . 1.386(3) ?
C5 H5A . 0.93 ?
C7 C8 . 1.486(3) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C10 C16 . 1.339(2) ?
C10 C11 . 1.483(2) ?
C11 C12 . 1.467(2) ?
C12 C13 . 1.364(3) ?
C13 C14 . 1.413(3) ?
C13 H13A . 0.93 ?
C14 C15 . 1.354(3) ?
C15 H15A . 0.93 ?
C16 C17 . 1.468(2) ?
C16 H16A . 0.93 ?
C17 C22 . 1.391(3) ?
C17 C18 . 1.397(3) ?
C18 C19 . 1.384(3) ?
C18 H18A . 0.93 ?
C19 C20 . 1.377(3) ?
C19 H19A . 0.93 ?
C20 C21 . 1.381(3) ?
C21 C22 . 1.383(3) ?
C21 H21A . 0.93 ?
C22 H22A . 0.93 ?
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
_geom_hbond_publ_flag
C15 H15A N2 1_665 0.93 2.60 3.495(3) 162 yes
C21 H21A Cl1 1_546 0.93 2.81 3.691(2) 159 yes
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
C8 N1 N2 C9 . . . . -0.1(2) ?
C9 N3 N4 C11 . . . . -21.5(3) ?
C8 N3 N4 C11 . . . . 166.81(17) ?
C6 C1 C2 C3 . . . . 0.0(3) ?
C1 C2 C3 C4 . . . . -1.3(3) ?
C1 C2 C3 Cl1 . . . . 178.71(16) ?
C2 C3 C4 C5 . . . . 0.8(4) ?
Cl1 C3 C4 C5 . . . . -179.26(18) ?
C3 C4 C5 C6 . . . . 1.1(4) ?
C7 O1 C6 C5 . . . . 161.28(18) ?
C7 O1 C6 C1 . . . . -19.9(3) ?
C4 C5 C6 O1 . . . . 176.5(2) ?
C4 C5 C6 C1 . . . . -2.4(3) ?
C2 C1 C6 O1 . . . . -176.98(18) ?
C2 C1 C6 C5 . . . . 1.8(3) ?
C6 O1 C7 C8 . . . . -172.11(16) ?
N2 N1 C8 N3 . . . . -0.7(2) ?
N2 N1 C8 C7 . . . . -174.39(17) ?
C9 N3 C8 N1 . . . . 1.1(2) ?
N4 N3 C8 N1 . . . . 174.43(16) ?
C9 N3 C8 C7 . . . . 174.73(17) ?
N4 N3 C8 C7 . . . . -12.0(3) ?
O1 C7 C8 N1 . . . . -132.7(2) ?
O1 C7 C8 N3 . . . . 54.6(3) ?
N1 N2 C9 N3 . . . . 0.8(2) ?
N1 N2 C9 S1 . . . . -177.89(13) ?
C8 N3 C9 N2 . . . . -1.18(19) ?
N4 N3 C9 N2 . . . . -174.25(16) ?
C8 N3 C9 S1 . . . . 177.59(13) ?
N4 N3 C9 S1 . . . . 4.5(2) ?
C10 S1 C9 N2 . . . . -155.83(17) ?
C10 S1 C9 N3 . . . . 25.61(15) ?
C9 S1 C10 C16 . . . . 135.40(16) ?
C9 S1 C10 C11 . . . . -42.97(14) ?
N3 N4 C11 C12 . . . . 175.41(15) ?
N3 N4 C11 C10 . . . . -2.5(3) ?
C16 C10 C11 N4 . . . . -140.1(2) ?
S1 C10 C11 N4 . . . . 38.2(2) ?
C16 C10 C11 C12 . . . . 42.0(3) ?
S1 C10 C11 C12 . . . . -139.59(14) ?
N4 C11 C12 C13 . . . . -156.04(19) ?
C10 C11 C12 C13 . . . . 22.0(3) ?
N4 C11 C12 S2 . . . . 16.7(2) ?
C10 C11 C12 S2 . . . . -165.26(13) ?
C15 S2 C12 C13 . . . . -0.15(16) ?
C15 S2 C12 C11 . . . . -174.03(15) ?
C11 C12 C13 C14 . . . . 173.10(18) ?
S2 C12 C13 C14 . . . . -0.1(2) ?
C12 C13 C14 C15 . . . . 0.4(3) ?
C12 C13 C14 N5 . . . . -176.46(18) ?
O3 N5 C14 C15 . . . . -178.6(2) ?
O2 N5 C14 C15 . . . . 1.6(4) ?
O3 N5 C14 C13 . . . . -2.0(3) ?
O2 N5 C14 C13 . . . . 178.2(2) ?
C13 C14 C15 S2 . . . . -0.5(2) ?
N5 C14 C15 S2 . . . . 176.31(17) ?
C12 S2 C15 C14 . . . . 0.37(16) ?
C11 C10 C16 C17 . . . . 177.31(17) ?
S1 C10 C16 C17 . . . . -0.9(3) ?
C10 C16 C17 C22 . . . . 39.3(3) ?
C10 C16 C17 C18 . . . . -141.3(2) ?
C22 C17 C18 C19 . . . . -2.3(3) ?
C16 C17 C18 C19 . . . . 178.31(18) ?
C17 C18 C19 C20 . . . . 0.9(3) ?
C18 C19 C20 C21 . . . . 0.7(3) ?
C18 C19 C20 Cl2 . . . . 179.75(16) ?
C19 C20 C21 C22 . . . . -0.8(3) ?
Cl2 C20 C21 C22 . . . . -179.87(15) ?
C20 C21 C22 C17 . . . . -0.6(3) ?
C18 C17 C22 C21 . . . . 2.2(3) ?
C16 C17 C22 C21 . . . . -178.45(18) ?
