#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/96/2229667.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_2229667
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Hemamalini, Madhukar'
Nithinchandra
'Kalluraya, Balakrishna'
_publ_section_title
;
 4-({[6-(4-Chlorobenzyl)-4-methyl-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfanyl}acetyl)-3-phenylsydnone
;
_journal_coeditor_code           HB5811
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o820
_journal_paper_doi               10.1107/S1600536811007689
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H16 Cl N5 O4 S'
_chemical_formula_moiety         'C21 H16 Cl N5 O4 S'
_chemical_formula_sum            'C21 H16 Cl N5 O4 S'
_chemical_formula_weight         469.90
_chemical_name_common
;
4-({[6-(4-Chlorobenzyl)-4-methyl-5-oxo-4,5-dihydro-1,2,4-triazin-3-
yl]sulfanyl}acetyl)-3-phenylsydnone
;
_chemical_name_systematic
;
4-({[6-(4-Chlorobenzyl)-4-methyl-5-oxo-4,5-dihydro-1,2,4-triazin-3-
yl]sulfanyl}acetyl)-3-phenyl-1,2,3-oxadiazol-3-ylium-5-olate
;
_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                105.2640(10)
_cell_angle_beta                 92.1030(10)
_cell_angle_gamma                97.3630(10)
_cell_formula_units_Z            2
_cell_length_a                   6.46040(10)
_cell_length_b                   10.1634(2)
_cell_length_c                   16.9901(4)
_cell_measurement_reflns_used    9469
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.31
_cell_measurement_theta_min      2.49
_cell_volume                     1064.44(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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21841
_diffrn_reflns_theta_full        30.44
_diffrn_reflns_theta_max         30.44
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.490
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         6389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0490
_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)+(0.0757P)²+0.3213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1542
_reflns_number_gt                4781
_reflns_number_total             6389
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5811.cif
_cod_data_source_block           I
_cod_database_code               2229667
_cod_database_fobs_code          2229667
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.62801(16) 0.17208(7) -0.44701(4) 0.0927(3) Uani d . 1 . .
S S1 0.74666(7) 0.42674(5) 0.10616(3) 0.04942(14) Uani d . 1 . .
O O1 0.8261(2) -0.00776(14) -0.09214(9) 0.0536(3) Uani d . 1 . .
O O2 0.4372(2) 0.37342(15) 0.22327(10) 0.0631(4) Uani d . 1 . .
O O3 0.2131(2) 0.70857(15) 0.14094(9) 0.0569(4) Uani d . 1 . .
O O4 -0.0096(2) 0.68960(14) 0.23895(9) 0.0525(3) Uani d . 1 . .
N N1 0.3637(2) 0.14727(17) -0.05789(10) 0.0455(3) Uani d . 1 . .
N N2 0.4389(2) 0.26204(16) 0.00528(9) 0.0432(3) Uani d . 1 . .
N N3 0.76804(19) 0.18731(14) 0.00212(8) 0.0357(3) Uani d . 1 . .
N N4 -0.0422(3) 0.61324(17) 0.29404(10) 0.0513(4) Uani d . 1 . .
N N5 0.1021(2) 0.53269(14) 0.28321(9) 0.0391(3) Uani d . 1 . .
C C1 0.6273(3) -0.0406(2) -0.28017(12) 0.0538(5) Uani d . 1 . .
H H1A 0.7109 -0.0981 -0.2639 0.065 Uiso calc R 1 . .
C C2 0.6816(4) 0.0139(2) -0.34463(13) 0.0614(5) Uani d . 1 . .
H H2A 0.8010 -0.0068 -0.3715 0.074 Uiso calc R 1 . .
C C3 0.5567(4) 0.0987(2) -0.36822(12) 0.0573(5) Uani d . 1 . .
C C4 0.3787(4) 0.1282(2) -0.33058(13) 0.0625(6) Uani d . 1 . .
H H4A 0.2938 0.1839 -0.3481 0.075 Uiso calc R 1 . .
C C5 0.3265(4) 0.0743(2) -0.26612(13) 0.0559(5) Uani d . 1 . .
H H5A 0.2063 0.0950 -0.2398 0.067 Uiso calc R 1 . .
C C6 0.4501(3) -0.01022(17) -0.23998(11) 0.0429(4) Uani d . 1 . .
C C7 0.3994(3) -0.05628(19) -0.16429(12) 0.0491(4) Uani d . 1 . .
H H7A 0.2491 -0.0782 -0.1632 0.059 Uiso calc R 1 . .
H H7B 0.4621 -0.1381 -0.1645 0.059 Uiso calc R 1 . .
C C8 0.4848(3) 0.05888(18) -0.09049(10) 0.0391(3) Uani d . 1 . .
C C9 0.7063(3) 0.07191(17) -0.06296(10) 0.0381(3) Uani d . 1 . .
C C10 0.6336(2) 0.27910(17) 0.03115(10) 0.0351(3) Uani d . 1 . .
C C11 0.9776(2) 0.22301(18) 0.03403(11) 0.0415(4) Uani d . 1 . .
H H11A 0.9900 0.3032 0.0799 0.062 Uiso calc R 1 . .
H H11B 1.0642 0.2424 -0.0074 0.062 Uiso calc R 1 . .
H H11C 1.0218 0.1478 0.0515 0.062 Uiso calc R 1 . .
C C12 0.5200(3) 0.51093(19) 0.13034(12) 0.0451(4) Uani d . 1 . .
H H12A 0.5638 0.6097 0.1483 0.054 Uiso calc R 1 . .
H H12B 0.4277 0.4916 0.0811 0.054 Uiso calc R 1 . .
C C13 0.3992(3) 0.46689(17) 0.19597(10) 0.0396(3) Uani d . 1 . .
C C14 0.2332(2) 0.54916(16) 0.22475(10) 0.0364(3) Uani d . 1 . .
C C15 0.1633(3) 0.65315(17) 0.19282(11) 0.0421(4) Uani d . 1 . .
C C16 0.0970(3) 0.44216(18) 0.33652(10) 0.0433(4) Uani d . 1 . .
C C17 0.2718(4) 0.4479(2) 0.38688(13) 0.0567(5) Uani d . 1 . .
H H17A 0.3960 0.5035 0.3843 0.068 Uiso calc R 1 . .
C C18 0.2562(5) 0.3678(3) 0.44141(15) 0.0719(7) Uani d . 1 . .
H H18A 0.3719 0.3693 0.4760 0.086 Uiso calc R 1 . .
C C19 0.0713(5) 0.2859(3) 0.44518(15) 0.0728(7) Uani d . 1 . .
H H19A 0.0623 0.2345 0.4832 0.087 Uiso calc R 1 . .
C C20 -0.1000(5) 0.2797(3) 0.39297(16) 0.0711(6) Uani d . 1 . .
H H20A -0.2230 0.2223 0.3947 0.085 Uiso calc R 1 . .
C C21 -0.0893(3) 0.3590(2) 0.33778(13) 0.0568(5) Uani d . 1 . .
H H21A -0.2043 0.3564 0.3026 0.068 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'
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
C10 S1 C12 . . 100.06(8) ?
N4 O4 C15 . . 110.86(12) ?
C8 N1 N2 . . 120.99(14) ?
C10 N2 N1 . . 118.28(14) ?
C10 N3 C9 . . 121.17(13) ?
C10 N3 C11 . . 117.25(14) ?
C9 N3 C11 . . 121.14(13) ?
N5 N4 O4 . . 105.20(13) ?
N4 N5 C14 . . 114.60(14) ?
N4 N5 C16 . . 114.42(14) ?
C14 N5 C16 . . 130.97(13) ?
C6 C1 C2 . . 120.63(18) ?
C6 C1 H1A . . 119.7 ?
C2 C1 H1A . . 119.7 ?
C3 C2 C1 . . 119.2(2) ?
C3 C2 H2A . . 120.4 ?
C1 C2 H2A . . 120.4 ?
C4 C3 C2 . . 121.4(2) ?
C4 C3 Cl1 . . 119.07(17) ?
C2 C3 Cl1 . . 119.57(19) ?
C3 C4 C5 . . 119.04(19) ?
C3 C4 H4A . . 120.5 ?
C5 C4 H4A . . 120.5 ?
C4 C5 C6 . . 121.2(2) ?
C4 C5 H5A . . 119.4 ?
C6 C5 H5A . . 119.4 ?
C1 C6 C5 . . 118.58(18) ?
C1 C6 C7 . . 121.61(17) ?
C5 C6 C7 . . 119.59(17) ?
C8 C7 C6 . . 108.29(14) ?
C8 C7 H7A . . 110.0 ?
C6 C7 H7A . . 110.0 ?
C8 C7 H7B . . 110.0 ?
C6 C7 H7B . . 110.0 ?
H7A C7 H7B . . 108.4 ?
N1 C8 C9 . . 123.14(16) ?
N1 C8 C7 . . 118.42(16) ?
C9 C8 C7 . . 118.25(15) ?
O1 C9 N3 . . 122.23(16) ?
O1 C9 C8 . . 125.41(17) ?
N3 C9 C8 . . 112.36(13) ?
N2 C10 N3 . . 123.91(16) ?
N2 C10 S1 . . 121.47(12) ?
N3 C10 S1 . . 114.61(11) ?
N3 C11 H11A . . 109.5 ?
N3 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N3 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 S1 . . 113.61(12) ?
C13 C12 H12A . . 108.8 ?
S1 C12 H12A . . 108.8 ?
C13 C12 H12B . . 108.8 ?
S1 C12 H12B . . 108.8 ?
H12A C12 H12B . . 107.7 ?
O2 C13 C14 . . 122.62(16) ?
O2 C13 C12 . . 123.39(15) ?
C14 C13 C12 . . 113.98(14) ?
N5 C14 C15 . . 105.91(13) ?
N5 C14 C13 . . 126.38(14) ?
C15 C14 C13 . . 127.49(15) ?
O3 C15 O4 . . 120.05(15) ?
O3 C15 C14 . . 136.52(17) ?
O4 C15 C14 . . 103.43(14) ?
C17 C16 C21 . . 122.79(18) ?
C17 C16 N5 . . 119.23(17) ?
C21 C16 N5 . . 117.87(16) ?
C16 C17 C18 . . 117.6(2) ?
C16 C17 H17A . . 121.2 ?
C18 C17 H17A . . 121.2 ?
C19 C18 C17 . . 120.9(2) ?
C19 C18 H18A . . 119.5 ?
C17 C18 H18A . . 119.5 ?
C20 C19 C18 . . 120.3(2) ?
C20 C19 H19A . . 119.8 ?
C18 C19 H19A . . 119.8 ?
C19 C20 C21 . . 120.1(2) ?
C19 C20 H20A . . 120.0 ?
C21 C20 H20A . . 120.0 ?
C16 C21 C20 . . 118.2(2) ?
C16 C21 H21A . . 120.9 ?
C20 C21 H21A . . 120.9 ?
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
Cl1 C3 . 1.744(2) ?
S1 C10 . 1.7472(18) ?
S1 C12 . 1.7960(17) ?
O1 C9 . 1.2159(19) ?
O2 C13 . 1.209(2) ?
O3 C15 . 1.197(2) ?
O4 N4 . 1.370(2) ?
O4 C15 . 1.420(2) ?
N1 C8 . 1.295(2) ?
N1 N2 . 1.381(2) ?
N2 C10 . 1.292(2) ?
N3 C10 . 1.3655(18) ?
N3 C9 . 1.386(2) ?
N3 C11 . 1.4055(19) ?
N4 N5 . 1.3046(19) ?
N5 C14 . 1.358(2) ?
N5 C16 . 1.449(2) ?
C1 C6 . 1.381(3) ?
C1 C2 . 1.388(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.375(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.365(3) ?
C4 C5 . 1.382(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.387(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.513(3) ?
C7 C8 . 1.503(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.468(2) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.513(2) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.463(2) ?
C14 C15 . 1.422(2) ?
C16 C17 . 1.377(3) ?
C16 C21 . 1.383(3) ?
C17 C18 . 1.383(3) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.379(4) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.377(4) ?
C19 H19A . 0.9300 ?
C20 C21 . 1.386(3) ?
C20 H20A . 0.9300 ?
C21 H21A . 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
_geom_hbond_publ_flag
C7 H7B O2 2_655 0.97 2.52 3.429(3) 157 yes
C11 H11A S1 . 0.96 2.12 2.7577(17) 122 yes
C11 H11B N1 1_655 0.96 2.36 3.066(2) 130 yes
C11 H11B N2 1_655 0.96 2.40 3.0304(19) 123 yes
C11 H11C O1 2_755 0.96 2.07 3.021(2) 169 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 C10 . . . . 0.0(2) ?
C15 O4 N4 N5 . . . . -0.1(2) ?
O4 N4 N5 C14 . . . . 0.5(2) ?
O4 N4 N5 C16 . . . . 179.66(14) ?
C6 C1 C2 C3 . . . . 0.0(3) ?
C1 C2 C3 C4 . . . . -1.3(3) ?
C1 C2 C3 Cl1 . . . . 177.98(17) ?
C2 C3 C4 C5 . . . . 1.7(3) ?
Cl1 C3 C4 C5 . . . . -177.58(17) ?
C3 C4 C5 C6 . . . . -0.8(3) ?
C2 C1 C6 C5 . . . . 0.8(3) ?
C2 C1 C6 C7 . . . . -173.70(19) ?
C4 C5 C6 C1 . . . . -0.4(3) ?
C4 C5 C6 C7 . . . . 174.22(19) ?
C1 C6 C7 C8 . . . . 94.1(2) ?
C5 C6 C7 C8 . . . . -80.3(2) ?
N2 N1 C8 C9 . . . . 0.8(3) ?
N2 N1 C8 C7 . . . . -174.08(15) ?
C6 C7 C8 N1 . . . . 91.90(19) ?
C6 C7 C8 C9 . . . . -83.27(19) ?
C10 N3 C9 O1 . . . . 176.61(15) ?
C11 N3 C9 O1 . . . . 4.5(2) ?
C10 N3 C9 C8 . . . . -3.8(2) ?
C11 N3 C9 C8 . . . . -175.91(14) ?
N1 C8 C9 O1 . . . . -179.33(17) ?
C7 C8 C9 O1 . . . . -4.4(2) ?
N1 C8 C9 N3 . . . . 1.0(2) ?
C7 C8 C9 N3 . . . . 175.98(14) ?
N1 N2 C10 N3 . . . . -2.9(2) ?
N1 N2 C10 S1 . . . . 175.76(12) ?
C9 N3 C10 N2 . . . . 5.0(2) ?
C11 N3 C10 N2 . . . . 177.45(16) ?
C9 N3 C10 S1 . . . . -173.73(11) ?
C11 N3 C10 S1 . . . . -1.28(19) ?
C12 S1 C10 N2 . . . . 4.33(16) ?
C12 S1 C10 N3 . . . . -176.91(12) ?
C10 S1 C12 C13 . . . . 87.66(14) ?
S1 C12 C13 O2 . . . . -7.7(2) ?
S1 C12 C13 C14 . . . . 171.37(13) ?
N4 N5 C14 C15 . . . . -0.7(2) ?
C16 N5 C14 C15 . . . . -179.67(17) ?
N4 N5 C14 C13 . . . . -175.56(16) ?
C16 N5 C14 C13 . . . . 5.5(3) ?
O2 C13 C14 N5 . . . . -0.6(3) ?
C12 C13 C14 N5 . . . . -179.66(16) ?
O2 C13 C14 C15 . . . . -174.35(19) ?
C12 C13 C14 C15 . . . . 6.6(3) ?
N4 O4 C15 O3 . . . . 179.13(17) ?
N4 O4 C15 C14 . . . . -0.28(19) ?
N5 C14 C15 O3 . . . . -178.7(2) ?
C13 C14 C15 O3 . . . . -3.9(4) ?
N5 C14 C15 O4 . . . . 0.54(18) ?
C13 C14 C15 O4 . . . . 175.34(16) ?
N4 N5 C16 C17 . . . . -122.28(19) ?
C14 N5 C16 C17 . . . . 56.7(3) ?
N4 N5 C16 C21 . . . . 54.0(2) ?
C14 N5 C16 C21 . . . . -127.0(2) ?
C21 C16 C17 C18 . . . . -1.0(3) ?
N5 C16 C17 C18 . . . . 175.10(19) ?
C16 C17 C18 C19 . . . . -0.3(4) ?
C17 C18 C19 C20 . . . . 1.7(4) ?
C18 C19 C20 C21 . . . . -1.8(4) ?
C17 C16 C21 C20 . . . . 0.8(3) ?
N5 C16 C21 C20 . . . . -175.31(19) ?
C19 C20 C21 C16 . . . . 0.6(4) ?
