#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/97/2229721.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_2229721
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
Nithinchandra
'Kalluraya, Balakrishna'
_publ_section_title
;
 3-(p-Tolyl)-4-{3-[(phenylamino)methyl]-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-yl}sydnone
;
_journal_coeditor_code           IS2692
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1005
_journal_page_last               o1006
_journal_paper_doi               10.1107/S1600536811010786
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H17 N7 O2 S'
_chemical_formula_moiety         'C20 H17 N7 O2 S'
_chemical_formula_sum            'C20 H17 N7 O2 S'
_chemical_formula_weight         419.47
_chemical_name_common
;
3-(p-Tolyl)-4-{3-[(phenylamino)methyl]-7H-[1,2,4]triazolo[3,4-\
b][1,3,4]thiadiazin-6-yl}sydnone
;
_chemical_name_systematic
;
3-(4-methylphenyl)-4-{3-[(phenylamino)methyl]-
7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl}-1,2,3-
oxadiazol-3-ium-5-olate
;
_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
_cell_angle_beta                 114.550(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1210(4)
_cell_length_b                   10.5065(4)
_cell_length_c                   19.6370(6)
_cell_measurement_reflns_used    8225
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.54
_cell_measurement_theta_min      2.80
_cell_volume                     1899.36(12)
_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      100
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Bruker SMART APEXII DUO CCD area-detector diffractometer
;
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22363
_diffrn_reflns_theta_full        32.60
_diffrn_reflns_theta_max         32.60
_diffrn_reflns_theta_min         2.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.9472
_exptl_absorpt_correction_T_min  0.9324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.267
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         6845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0589P)²+0.4436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                5754
_reflns_number_total             6845
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2692.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229721
_cod_database_fobs_code          2229721
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
S S1 0.76994(3) 0.59534(2) 1.086823(13) 0.01634(7) Uani d . 1 . .
O O1 0.29144(9) 0.96219(7) 1.00427(4) 0.01957(15) Uani d . 1 . .
O O2 0.51181(10) 0.92364(7) 1.10036(4) 0.02034(16) Uani d . 1 . .
N N1 0.39442(11) 0.30819(8) 0.79980(5) 0.01940(18) Uani d . 1 . .
H H1 0.4424 0.2500 0.8313 0.023 Uiso d R 1 . .
N N2 0.66867(10) 0.35357(8) 0.92354(5) 0.01599(16) Uani d . 1 . .
N N3 0.76192(10) 0.39417(8) 0.99600(5) 0.01605(16) Uani d . 1 . .
N N4 0.59144(9) 0.53924(8) 0.94311(4) 0.01301(15) Uani d . 1 . .
N N5 0.49010(9) 0.63271(8) 0.93523(4) 0.01330(15) Uani d . 1 . .
N N6 0.29928(10) 0.84348(8) 0.91836(4) 0.01433(15) Uani d . 1 . .
N N7 0.21520(11) 0.92571(9) 0.93095(5) 0.01882(17) Uani d . 1 . .
C C1 0.24653(12) 0.35564(10) 0.66818(6) 0.01858(19) Uani d . 1 . .
H H1A 0.2696 0.4417 0.6759 0.022 Uiso calc R 1 . .
C C2 0.15334(12) 0.31226(11) 0.59701(6) 0.0203(2) Uani d . 1 . .
H H2A 0.1146 0.3701 0.5578 0.024 Uiso calc R 1 . .
C C3 0.11761(12) 0.18408(11) 0.58390(6) 0.0203(2) Uani d . 1 . .
H H3A 0.0557 0.1559 0.5364 0.024 Uiso calc R 1 . .
C C4 0.17654(12) 0.09824(10) 0.64352(6) 0.01943(19) Uani d . 1 . .
H H4A 0.1535 0.0123 0.6355 0.023 Uiso calc R 1 . .
C C5 0.26881(12) 0.13991(10) 0.71441(6) 0.01743(18) Uani d . 1 . .
H H5A 0.3070 0.0817 0.7534 0.021 Uiso calc R 1 . .
C C6 0.30514(11) 0.26966(9) 0.72776(5) 0.01523(17) Uani d . 1 . .
C C7 0.44975(12) 0.43689(9) 0.81634(5) 0.01550(17) Uani d . 1 . .
H H7A 0.3723 0.4945 0.8128 0.019 Uiso calc R 1 . .
H H7B 0.4872 0.4638 0.7805 0.019 Uiso calc R 1 . .
C C8 0.56801(11) 0.44026(9) 0.89361(5) 0.01385(17) Uani d . 1 . .
C C9 0.71259(11) 0.50470(9) 1.00598(5) 0.01399(16) Uani d . 1 . .
C C10 0.68936(11) 0.74328(9) 1.03967(6) 0.01621(18) Uani d . 1 . .
H H10A 0.6906 0.8051 1.0766 0.019 Uiso calc R 1 . .
H H10B 0.7477 0.7769 1.0152 0.019 Uiso calc R 1 . .
C C11 0.53525(11) 0.72606(9) 0.98234(5) 0.01326(16) Uani d . 1 . .
C C12 0.42909(11) 0.82264(9) 0.97734(5) 0.01385(17) Uani d . 1 . .
C C13 0.42779(12) 0.90140(9) 1.03598(5) 0.01612(18) Uani d . 1 . .
C C14 0.24541(11) 0.79366(9) 0.84281(5) 0.01405(17) Uani d . 1 . .
C C15 0.10991(12) 0.73640(11) 0.81278(6) 0.0201(2) Uani d . 1 . .
H H15A 0.0557 0.7275 0.8409 0.024 Uiso calc R 1 . .
C C16 0.05717(12) 0.69250(12) 0.73922(6) 0.0215(2) Uani d . 1 . .
H H16A -0.0334 0.6534 0.7180 0.026 Uiso calc R 1 . .
C C17 0.13799(12) 0.70619(10) 0.69677(5) 0.01611(18) Uani d . 1 . .
C C18 0.27547(12) 0.76301(10) 0.72997(5) 0.01676(18) Uani d . 1 . .
H H18A 0.3308 0.7710 0.7024 0.020 Uiso calc R 1 . .
C C19 0.33082(12) 0.80769(10) 0.80326(5) 0.01638(18) Uani d . 1 . .
H H19A 0.4219 0.8457 0.8251 0.020 Uiso calc R 1 . .
C C20 0.07796(13) 0.66428(11) 0.61610(6) 0.0207(2) Uani d . 1 . .
H H20A 0.0210 0.5886 0.6099 0.031 Uiso calc R 1 . .
H H20B 0.1567 0.6470 0.6022 0.031 Uiso calc R 1 . .
H H20C 0.0180 0.7305 0.5848 0.031 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'
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
C9 S1 C10 . . 95.43(5) ?
N7 O1 C13 . . 110.89(8) ?
C6 N1 C7 . . 121.96(8) ?
C6 N1 H1 . . 117.3 ?
C7 N1 H1 . . 116.9 ?
C8 N2 N3 . . 108.22(8) ?
C9 N3 N2 . . 106.42(8) ?
C8 N4 C9 . . 105.18(8) ?
C8 N4 N5 . . 123.82(8) ?
C9 N4 N5 . . 129.05(8) ?
C11 N5 N4 . . 115.69(8) ?
N7 N6 C12 . . 114.83(8) ?
N7 N6 C14 . . 115.79(8) ?
C12 N6 C14 . . 129.26(8) ?
N6 N7 O1 . . 104.84(8) ?
C2 C1 C6 . . 120.04(10) ?
C2 C1 H1A . . 120.0 ?
C6 C1 H1A . . 120.0 ?
C3 C2 C1 . . 121.08(10) ?
C3 C2 H2A . . 119.5 ?
C1 C2 H2A . . 119.5 ?
C2 C3 C4 . . 118.79(10) ?
C2 C3 H3A . . 120.6 ?
C4 C3 H3A . . 120.6 ?
C5 C4 C3 . . 120.77(10) ?
C5 C4 H4A . . 119.6 ?
C3 C4 H4A . . 119.6 ?
C4 C5 C6 . . 120.51(9) ?
C4 C5 H5A . . 119.7 ?
C6 C5 H5A . . 119.7 ?
N1 C6 C1 . . 122.34(9) ?
N1 C6 C5 . . 118.82(9) ?
C1 C6 C5 . . 118.81(9) ?
N1 C7 C8 . . 108.80(8) ?
N1 C7 H7A . . 109.9 ?
C8 C7 H7A . . 109.9 ?
N1 C7 H7B . . 109.9 ?
C8 C7 H7B . . 109.9 ?
H7A C7 H7B . . 108.3 ?
N2 C8 N4 . . 109.59(8) ?
N2 C8 C7 . . 125.84(9) ?
N4 C8 C7 . . 124.51(9) ?
N3 C9 N4 . . 110.58(8) ?
N3 C9 S1 . . 128.39(8) ?
N4 C9 S1 . . 120.71(7) ?
C11 C10 S1 . . 112.54(7) ?
C11 C10 H10A . . 109.1 ?
S1 C10 H10A . . 109.1 ?
C11 C10 H10B . . 109.1 ?
S1 C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.8 ?
N5 C11 C12 . . 116.74(9) ?
N5 C11 C10 . . 124.96(9) ?
C12 C11 C10 . . 118.28(8) ?
N6 C12 C13 . . 105.37(9) ?
N6 C12 C11 . . 126.59(8) ?
C13 C12 C11 . . 127.41(9) ?
O2 C13 O1 . . 120.33(9) ?
O2 C13 C12 . . 135.62(10) ?
O1 C13 C12 . . 104.05(8) ?
C15 C14 C19 . . 122.95(9) ?
C15 C14 N6 . . 118.54(9) ?
C19 C14 N6 . . 118.50(9) ?
C14 C15 C16 . . 118.04(10) ?
C14 C15 H15A . . 121.0 ?
C16 C15 H15A . . 121.0 ?
C15 C16 C17 . . 121.14(10) ?
C15 C16 H16A . . 119.4 ?
C17 C16 H16A . . 119.4 ?
C16 C17 C18 . . 118.74(9) ?
C16 C17 C20 . . 121.11(10) ?
C18 C17 C20 . . 120.13(9) ?
C19 C18 C17 . . 121.34(9) ?
C19 C18 H18A . . 119.3 ?
C17 C18 H18A . . 119.3 ?
C14 C19 C18 . . 117.77(10) ?
C14 C19 H19A . . 121.1 ?
C18 C19 H19A . . 121.1 ?
C17 C20 H20A . . 109.5 ?
C17 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C17 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
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 . 1.7315(10) ?
S1 C10 . 1.8196(10) ?
O1 N7 . 1.3756(12) ?
O1 C13 . 1.4093(13) ?
O2 C13 . 1.2177(12) ?
N1 C6 . 1.3855(12) ?
N1 C7 . 1.4479(13) ?
N1 H1 . 0.8621 ?
N2 C8 . 1.3097(13) ?
N2 N3 . 1.4075(12) ?
N3 C9 . 1.3106(13) ?
N4 C8 . 1.3751(12) ?
N4 C9 . 1.3790(12) ?
N4 N5 . 1.3814(11) ?
N5 C11 . 1.2943(12) ?
N6 N7 . 1.3063(12) ?
N6 C12 . 1.3605(13) ?
N6 C14 . 1.4491(12) ?
C1 C2 . 1.3983(14) ?
C1 C6 . 1.3999(14) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.3904(16) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.3998(16) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.3861(14) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.4079(14) ?
C5 H5A . 0.9300 ?
C7 C8 . 1.4924(14) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C10 C11 . 1.5079(14) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.4511(14) ?
C12 C13 . 1.4226(13) ?
C14 C15 . 1.3851(15) ?
C14 C19 . 1.3893(14) ?
C15 C16 . 1.3941(15) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.3968(15) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.4013(15) ?
C17 C20 . 1.5075(14) ?
C18 C19 . 1.3914(13) ?
C18 H18A . 0.9300 ?
C19 H19A . 0.9300 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
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
C10 H10A O2 . 0.97 2.40 3.1654(14) 136 yes
N1 H1 O2 3_667 0.86 2.20 3.0218(11) 160 yes
C18 H18A N2 2_656 0.93 2.62 3.4246(14) 145 yes
C15 H15A Cg1 2_556 0.93 2.73 3.5537(14) 148 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 N2 N3 C9 . . . . -0.32(11) ?
C8 N4 N5 C11 . . . . -172.93(9) ?
C9 N4 N5 C11 . . . . 25.42(14) ?
C12 N6 N7 O1 . . . . -1.21(12) ?
C14 N6 N7 O1 . . . . -177.58(8) ?
C13 O1 N7 N6 . . . . 1.44(11) ?
C6 C1 C2 C3 . . . . -0.22(17) ?
C1 C2 C3 C4 . . . . 0.11(17) ?
C2 C3 C4 C5 . . . . 0.03(17) ?
C3 C4 C5 C6 . . . . -0.06(17) ?
C7 N1 C6 C1 . . . . -8.93(16) ?
C7 N1 C6 C5 . . . . 172.89(10) ?
C2 C1 C6 N1 . . . . -177.99(11) ?
C2 C1 C6 C5 . . . . 0.19(16) ?
C4 C5 C6 N1 . . . . 178.20(10) ?
C4 C5 C6 C1 . . . . -0.05(16) ?
C6 N1 C7 C8 . . . . -166.77(10) ?
N3 N2 C8 N4 . . . . 0.91(11) ?
N3 N2 C8 C7 . . . . 178.01(9) ?
C9 N4 C8 N2 . . . . -1.12(11) ?
N5 N4 C8 N2 . . . . -166.45(9) ?
C9 N4 C8 C7 . . . . -178.27(9) ?
N5 N4 C8 C7 . . . . 16.41(15) ?
N1 C7 C8 N2 . . . . 40.77(14) ?
N1 C7 C8 N4 . . . . -142.55(10) ?
N2 N3 C9 N4 . . . . -0.40(11) ?
N2 N3 C9 S1 . . . . 173.15(8) ?
C8 N4 C9 N3 . . . . 0.92(11) ?
N5 N4 C9 N3 . . . . 165.20(9) ?
C8 N4 C9 S1 . . . . -173.20(7) ?
N5 N4 C9 S1 . . . . -8.92(14) ?
C10 S1 C9 N3 . . . . 161.54(10) ?
C10 S1 C9 N4 . . . . -25.49(9) ?
C9 S1 C10 C11 . . . . 46.28(8) ?
N4 N5 C11 C12 . . . . -177.38(8) ?
N4 N5 C11 C10 . . . . 4.59(14) ?
S1 C10 C11 N5 . . . . -43.10(12) ?
S1 C10 C11 C12 . . . . 138.89(8) ?
N7 N6 C12 C13 . . . . 0.52(12) ?
C14 N6 C12 C13 . . . . 176.30(9) ?
N7 N6 C12 C11 . . . . 171.94(9) ?
C14 N6 C12 C11 . . . . -12.28(16) ?
N5 C11 C12 N6 . . . . -17.48(15) ?
C10 C11 C12 N6 . . . . 160.69(9) ?
N5 C11 C12 C13 . . . . 152.08(10) ?
C10 C11 C12 C13 . . . . -29.75(15) ?
N7 O1 C13 O2 . . . . 178.77(9) ?
N7 O1 C13 C12 . . . . -1.14(11) ?
N6 C12 C13 O2 . . . . -179.49(12) ?
C11 C12 C13 O2 . . . . 9.2(2) ?
N6 C12 C13 O1 . . . . 0.39(10) ?
C11 C12 C13 O1 . . . . -170.93(9) ?
N7 N6 C14 C15 . . . . -55.54(13) ?
C12 N6 C14 C15 . . . . 128.71(11) ?
N7 N6 C14 C19 . . . . 123.23(10) ?
C12 N6 C14 C19 . . . . -52.52(14) ?
C19 C14 C15 C16 . . . . -0.75(16) ?
N6 C14 C15 C16 . . . . 177.97(10) ?
C14 C15 C16 C17 . . . . -0.28(17) ?
C15 C16 C17 C18 . . . . 1.25(17) ?
C15 C16 C17 C20 . . . . -177.10(11) ?
C16 C17 C18 C19 . . . . -1.25(16) ?
C20 C17 C18 C19 . . . . 177.12(10) ?
C15 C14 C19 C18 . . . . 0.75(15) ?
N6 C14 C19 C18 . . . . -177.96(9) ?
C17 C18 C19 C14 . . . . 0.28(15) ?
