#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/97/2229757.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_2229757
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
Nithinchandra
'Kalluraya, Balakrishna'
_publ_section_title
;
 4-({[4-Amino-6-(p-bromobenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfanyl}acetyl)-3-phenylsydnone
;
_journal_coeditor_code           LH5224
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1004
_journal_paper_doi               10.1107/S1600536811010798
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H15 Br N6 O4 S'
_chemical_formula_moiety         'C20 H15 Br N6 O4 S'
_chemical_formula_sum            'C20 H15 Br N6 O4 S'
_chemical_formula_weight         515.35
_chemical_name_common
;
4-({[4-Amino-6-(p-bromobenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]
sulfanyl}acetyl)-3-phenylsydnone
;
_chemical_name_systematic
;
4-({[4-Amino-6-(p-bromobenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]
sulfanyl}acetyl)-3-phenylsydnone
;
_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                104.8730(10)
_cell_angle_beta                 93.5070(10)
_cell_angle_gamma                98.1890(10)
_cell_formula_units_Z            2
_cell_length_a                   6.3842(3)
_cell_length_b                   10.0832(5)
_cell_length_c                   17.1563(8)
_cell_measurement_reflns_used    8506
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.47
_cell_volume                     1050.99(9)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21938
_diffrn_reflns_theta_full        30.24
_diffrn_reflns_theta_max         30.24
_diffrn_reflns_theta_min         2.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.097
_exptl_absorpt_correction_T_max  0.8916
_exptl_absorpt_correction_T_min  0.5525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.946
_refine_diff_density_min         -0.497
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         6161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0469P)²+0.5765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                5241
_reflns_number_total             6161
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5224.cif
_cod_data_source_block           I
_cod_database_code               2229757
_cod_database_fobs_code          2229757
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
Br Br1 0.14494(4) 0.177407(19) -0.446529(11) 0.02915(7) Uani d . 1 . .
S S1 0.25040(6) 0.42973(4) 0.10384(3) 0.01811(9) Uani d . 1 . .
O O1 -0.50655(19) 0.68942(12) 0.23590(8) 0.0188(2) Uani d . 1 . .
O O2 -0.2801(2) 0.71471(13) 0.14077(8) 0.0208(3) Uani d . 1 . .
O O3 -0.0592(2) 0.36960(13) 0.21831(8) 0.0220(3) Uani d . 1 . .
O O4 0.3090(2) -0.01318(13) -0.08910(8) 0.0205(3) Uani d . 1 . .
N N1 -0.3930(2) 0.52932(14) 0.27862(9) 0.0149(3) Uani d . 1 . .
N N2 -0.5387(2) 0.60958(15) 0.28897(9) 0.0186(3) Uani d . 1 . .
N N3 -0.0707(2) 0.26436(15) 0.00189(9) 0.0170(3) Uani d . 1 . .
N N4 -0.1524(2) 0.14792(15) -0.06048(9) 0.0181(3) Uani d . 1 . .
N N5 0.2602(2) 0.18642(14) 0.00230(9) 0.0143(3) Uani d . 1 . .
N N6 0.4749(2) 0.22357(17) 0.03542(11) 0.0206(3) Uani d . 1 . .
C C1 -0.2106(3) 0.44195(17) 0.37978(11) 0.0196(3) Uani d . 1 . .
H H1A -0.0839 0.4967 0.3756 0.024 Uiso calc R 1 . .
C C2 -0.2207(3) 0.36200(19) 0.43441(11) 0.0238(4) Uani d . 1 . .
H H2A -0.0994 0.3628 0.4675 0.029 Uiso calc R 1 . .
C C3 -0.4115(3) 0.28031(19) 0.44025(12) 0.0259(4) Uani d . 1 . .
H H3A -0.4172 0.2280 0.4777 0.031 Uiso calc R 1 . .
C C4 -0.5930(3) 0.2768(2) 0.39032(12) 0.0248(4) Uani d . 1 . .
H H4A -0.7196 0.2214 0.3940 0.030 Uiso calc R 1 . .
C C5 -0.5857(3) 0.35610(18) 0.33486(11) 0.0200(3) Uani d . 1 . .
H H5A -0.7060 0.3541 0.3009 0.024 Uiso calc R 1 . .
C C6 -0.3950(3) 0.43812(16) 0.33132(10) 0.0159(3) Uani d . 1 . .
C C7 -0.3307(3) 0.65627(16) 0.19113(10) 0.0158(3) Uani d . 1 . .
C C8 -0.2595(3) 0.54977(16) 0.22188(10) 0.0147(3) Uani d . 1 . .
C C9 -0.0958(3) 0.46663(16) 0.19248(10) 0.0155(3) Uani d . 1 . .
C C10 0.0227(3) 0.51392(17) 0.12772(11) 0.0171(3) Uani d . 1 . .
H H10A 0.0694 0.6137 0.1461 0.021 Uiso calc R 1 . .
H H10B -0.0740 0.4948 0.0789 0.021 Uiso calc R 1 . .
C C11 0.1283(2) 0.28045(16) 0.02926(10) 0.0140(3) Uani d . 1 . .
C C12 -0.0334(3) 0.05691(17) -0.09056(10) 0.0155(3) Uani d . 1 . .
C C13 0.1916(3) 0.06871(16) -0.06161(10) 0.0150(3) Uani d . 1 . .
C C14 -0.1255(3) -0.06046(17) -0.16342(11) 0.0186(3) Uani d . 1 . .
H H14A -0.2789 -0.0807 -0.1640 0.022 Uiso calc R 1 . .
H H14B -0.0672 -0.1437 -0.1621 0.022 Uiso calc R 1 . .
C C15 -0.0681(3) -0.01499(16) -0.23796(10) 0.0169(3) Uani d . 1 . .
C C16 -0.1898(3) 0.07165(18) -0.26599(11) 0.0204(3) Uani d . 1 . .
H H16A -0.3123 0.0922 -0.2421 0.024 Uiso calc R 1 . .
C C17 -0.1300(3) 0.12721(18) -0.32900(11) 0.0229(4) Uani d . 1 . .
H H17A -0.2116 0.1841 -0.3479 0.027 Uiso calc R 1 . .
C C18 0.0541(3) 0.09602(17) -0.36308(11) 0.0204(3) Uani d . 1 . .
C C19 0.1758(3) 0.00851(18) -0.33787(11) 0.0208(3) Uani d . 1 . .
H H19A 0.2972 -0.0125 -0.3625 0.025 Uiso calc R 1 . .
C C20 0.1132(3) -0.04737(17) -0.27502(11) 0.0191(3) Uani d . 1 . .
H H20A 0.1929 -0.1067 -0.2577 0.023 Uiso calc R 1 . .
H H1N6 0.538(4) 0.226(3) -0.0038(17) 0.032(7) Uiso d . 1 . .
H H2N6 0.512(4) 0.153(3) 0.0487(14) 0.021(6) Uiso d . 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'
Br Br -0.2901 2.4595 '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
C11 S1 C10 . . 99.93(8) ?
N2 O1 C7 . . 110.81(12) ?
N2 N1 C8 . . 114.46(14) ?
N2 N1 C6 . . 114.57(14) ?
C8 N1 C6 . . 130.92(14) ?
N1 N2 O1 . . 105.56(13) ?
C11 N3 N4 . . 118.15(13) ?
C12 N4 N3 . . 120.73(14) ?
C11 N5 C13 . . 121.19(13) ?
C11 N5 N6 . . 116.73(13) ?
C13 N5 N6 . . 121.61(13) ?
N5 N6 H1N6 . . 103.2(19) ?
N5 N6 H2N6 . . 107.7(15) ?
H1N6 N6 H2N6 . . 103(2) ?
C2 C1 C6 . . 118.14(17) ?
C2 C1 H1A . . 120.9 ?
C6 C1 H1A . . 120.9 ?
C1 C2 C3 . . 120.50(17) ?
C1 C2 H2A . . 119.8 ?
C3 C2 H2A . . 119.8 ?
C4 C3 C2 . . 120.25(18) ?
C4 C3 H3A . . 119.9 ?
C2 C3 H3A . . 119.9 ?
C3 C4 C5 . . 120.06(18) ?
C3 C4 H4A . . 120.0 ?
C5 C4 H4A . . 120.0 ?
C6 C5 C4 . . 118.46(17) ?
C6 C5 H5A . . 120.8 ?
C4 C5 H5A . . 120.8 ?
C5 C6 C1 . . 122.58(16) ?
C5 C6 N1 . . 118.14(15) ?
C1 C6 N1 . . 119.16(15) ?
O2 C7 C8 . . 136.11(16) ?
O2 C7 O1 . . 120.39(14) ?
C8 C7 O1 . . 103.49(14) ?
N1 C8 C7 . . 105.67(13) ?
N1 C8 C9 . . 126.27(14) ?
C7 C8 C9 . . 127.67(15) ?
O3 C9 C8 . . 122.63(16) ?
O3 C9 C10 . . 123.85(15) ?
C8 C9 C10 . . 113.52(13) ?
C9 C10 S1 . . 112.99(11) ?
C9 C10 H10A . . 109.0 ?
S1 C10 H10A . . 109.0 ?
C9 C10 H10B . . 109.0 ?
S1 C10 H10B . . 109.0 ?
H10A C10 H10B . . 107.8 ?
N3 C11 N5 . . 124.05(15) ?
N3 C11 S1 . . 121.47(12) ?
N5 C11 S1 . . 114.47(12) ?
N4 C12 C13 . . 123.59(15) ?
N4 C12 C14 . . 118.19(15) ?
C13 C12 C14 . . 118.02(14) ?
O4 C13 N5 . . 122.36(15) ?
O4 C13 C12 . . 125.46(16) ?
N5 C13 C12 . . 112.17(13) ?
C12 C14 C15 . . 107.41(13) ?
C12 C14 H14A . . 110.2 ?
C15 C14 H14A . . 110.2 ?
C12 C14 H14B . . 110.2 ?
C15 C14 H14B . . 110.2 ?
H14A C14 H14B . . 108.5 ?
C20 C15 C16 . . 119.23(16) ?
C20 C15 C14 . . 121.51(15) ?
C16 C15 C14 . . 119.03(15) ?
C17 C16 C15 . . 120.87(17) ?
C17 C16 H16A . . 119.6 ?
C15 C16 H16A . . 119.6 ?
C18 C17 C16 . . 118.47(16) ?
C18 C17 H17A . . 120.8 ?
C16 C17 H17A . . 120.8 ?
C17 C18 C19 . . 122.11(17) ?
C17 C18 Br1 . . 119.06(14) ?
C19 C18 Br1 . . 118.83(14) ?
C18 C19 C20 . . 118.84(16) ?
C18 C19 H19A . . 120.6 ?
C20 C19 H19A . . 120.6 ?
C19 C20 C15 . . 120.45(16) ?
C19 C20 H20A . . 119.8 ?
C15 C20 H20A . . 119.8 ?
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
Br1 C18 . 1.9049(18) ?
S1 C11 . 1.7508(17) ?
S1 C10 . 1.8020(16) ?
O1 N2 . 1.3680(19) ?
O1 C7 . 1.429(2) ?
O2 C7 . 1.200(2) ?
O3 C9 . 1.218(2) ?
O4 C13 . 1.2187(19) ?
N1 N2 . 1.3088(19) ?
N1 C8 . 1.368(2) ?
N1 C6 . 1.445(2) ?
N3 C11 . 1.300(2) ?
N3 N4 . 1.381(2) ?
N4 C12 . 1.300(2) ?
N5 C11 . 1.3680(19) ?
N5 C13 . 1.389(2) ?
N5 N6 . 1.4112(19) ?
N6 H1N6 . 0.81(3) ?
N6 H2N6 . 0.86(3) ?
C1 C2 . 1.383(3) ?
C1 C6 . 1.389(2) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.394(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.389(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.390(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.385(2) ?
C5 H5A . 0.9300 ?
C7 C8 . 1.428(2) ?
C8 C9 . 1.465(2) ?
C9 C10 . 1.519(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C12 C13 . 1.469(2) ?
C12 C14 . 1.504(2) ?
C14 C15 . 1.514(2) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C20 . 1.393(2) ?
C15 C16 . 1.401(2) ?
C16 C17 . 1.389(3) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.384(3) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.386(2) ?
C19 C20 . 1.393(3) ?
C19 H19A . 0.9300 ?
C20 H20A . 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
N6 H1N6 N3 1_655 0.81(3) 2.47(3) 2.9835(19) 123(2) yes
N6 H1N6 N4 1_655 0.81(3) 2.40(3) 3.050(2) 138(3) yes
N6 H2N6 O4 2_655 0.86(3) 2.15(3) 2.989(2) 164(2) yes
C14 H14B O3 2_555 0.97 2.50 3.416(2) 157 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 O1 . . . . 0.65(18) ?
C6 N1 N2 O1 . . . . 178.30(13) ?
C7 O1 N2 N1 . . . . -0.32(17) ?
C11 N3 N4 C12 . . . . 0.3(2) ?
C6 C1 C2 C3 . . . . -0.1(3) ?
C1 C2 C3 C4 . . . . 0.9(3) ?
C2 C3 C4 C5 . . . . -0.7(3) ?
C3 C4 C5 C6 . . . . -0.4(3) ?
C4 C5 C6 C1 . . . . 1.3(3) ?
C4 C5 C6 N1 . . . . -174.73(16) ?
C2 C1 C6 C5 . . . . -1.1(3) ?
C2 C1 C6 N1 . . . . 174.91(15) ?
N2 N1 C6 C5 . . . . 51.6(2) ?
C8 N1 C6 C5 . . . . -131.18(18) ?
N2 N1 C6 C1 . . . . -124.54(17) ?
C8 N1 C6 C1 . . . . 52.6(2) ?
N2 O1 C7 O2 . . . . 179.06(15) ?
N2 O1 C7 C8 . . . . -0.09(17) ?
N2 N1 C8 C7 . . . . -0.71(19) ?
C6 N1 C8 C7 . . . . -177.89(16) ?
N2 N1 C8 C9 . . . . -173.89(15) ?
C6 N1 C8 C9 . . . . 8.9(3) ?
O2 C7 C8 N1 . . . . -178.5(2) ?
O1 C7 C8 N1 . . . . 0.44(17) ?
O2 C7 C8 C9 . . . . -5.4(3) ?
O1 C7 C8 C9 . . . . 173.50(15) ?
N1 C8 C9 O3 . . . . -1.7(3) ?
C7 C8 C9 O3 . . . . -173.40(16) ?
N1 C8 C9 C10 . . . . 178.64(15) ?
C7 C8 C9 C10 . . . . 6.9(2) ?
O3 C9 C10 S1 . . . . -9.0(2) ?
C8 C9 C10 S1 . . . . 170.66(11) ?
C11 S1 C10 C9 . . . . 87.24(13) ?
N4 N3 C11 N5 . . . . -2.7(2) ?
N4 N3 C11 S1 . . . . 176.05(12) ?
C13 N5 C11 N3 . . . . 4.4(2) ?
N6 N5 C11 N3 . . . . 176.67(16) ?
C13 N5 C11 S1 . . . . -174.36(12) ?
N6 N5 C11 S1 . . . . -2.14(19) ?
C10 S1 C11 N3 . . . . 6.15(16) ?
C10 S1 C11 N5 . . . . -175.02(12) ?
N3 N4 C12 C13 . . . . 0.4(2) ?
N3 N4 C12 C14 . . . . -174.35(15) ?
C11 N5 C13 O4 . . . . 176.57(15) ?
N6 N5 C13 O4 . . . . 4.7(2) ?
C11 N5 C13 C12 . . . . -3.4(2) ?
N6 N5 C13 C12 . . . . -175.22(15) ?
N4 C12 C13 O4 . . . . -178.76(17) ?
C14 C12 C13 O4 . . . . -4.1(2) ?
N4 C12 C13 N5 . . . . 1.2(2) ?
C14 C12 C13 N5 . . . . 175.89(14) ?
N4 C12 C14 C15 . . . . 92.39(18) ?
C13 C12 C14 C15 . . . . -82.61(17) ?
C12 C14 C15 C20 . . . . 93.65(18) ?
C12 C14 C15 C16 . . . . -80.78(19) ?
C20 C15 C16 C17 . . . . -1.1(3) ?
C14 C15 C16 C17 . . . . 173.41(16) ?
C15 C16 C17 C18 . . . . -0.6(3) ?
C16 C17 C18 C19 . . . . 1.9(3) ?
C16 C17 C18 Br1 . . . . -177.44(13) ?
C17 C18 C19 C20 . . . . -1.4(3) ?
Br1 C18 C19 C20 . . . . 177.91(13) ?
C18 C19 C20 C15 . . . . -0.4(3) ?
C16 C15 C20 C19 . . . . 1.6(3) ?
C14 C15 C20 C19 . . . . -172.79(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24694363
