#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229914.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_2229914
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Loh, Wan-Sin'
Nithinchandra
'Kalluraya, Balakrishna'
_publ_section_title
;
 4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl}-3-phenylsydnone
;
_journal_coeditor_code           BQ2294
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1177
_journal_page_last               o1178
_journal_paper_doi               10.1107/S1600536811013912
_journal_volume                  67
_journal_year                    2011
_chemical_formula_moiety         'C18 H13 Cl N6 O2 S'
_chemical_formula_sum            'C18 H13 Cl N6 O2 S'
_chemical_formula_weight         412.85
_chemical_name_common
;
4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-
1,3,4-thiadiazin-5-yl}-3-phenylsydnone
;
_chemical_name_systematic
;
4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-
1,3,4-thiadiazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-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                96.6860(10)
_cell_angle_beta                 95.2850(10)
_cell_angle_gamma                95.2290(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3180(3)
_cell_length_b                   10.1567(5)
_cell_length_c                   12.4721(6)
_cell_measurement_reflns_used    8568
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      34.96
_cell_measurement_theta_min      2.81
_cell_volume                     911.92(7)
_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      100.00(10)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type
;
Bruker SMART APEXII DUO 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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18115
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         2.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_correction_T_min  0.8418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            'light purple'
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         6480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0390
_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)+(0.0611P)²+0.3032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                5506
_reflns_number_total             6480
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2294.cif
_cod_data_source_block           I
_cod_database_code               2229914
_cod_database_fobs_code          2229914
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 1.07800(5) 0.08403(3) -0.18284(3) 0.03779(9) Uani d . 1 . .
S S1 0.17791(4) 0.27870(3) 0.20939(2) 0.02534(8) Uani d . 1 . .
O O1 -0.27472(13) 0.52923(9) 0.54724(7) 0.02723(18) Uani d . 1 . .
O O2 -0.14178(14) 0.66439(9) 0.43584(8) 0.02957(19) Uani d . 1 . .
N N1 0.32516(14) 0.31817(9) 0.01686(8) 0.02134(17) Uani d . 1 . .
N N2 0.16931(14) 0.38648(10) 0.02374(7) 0.02176(17) Uani d . 1 . .
N N3 -0.07075(13) 0.42674(10) 0.12269(8) 0.02133(17) Uani d . 1 . .
N N4 -0.14591(13) 0.45733(9) 0.21809(7) 0.01985(17) Uani d . 1 . .
N N5 -0.27251(13) 0.33810(9) 0.45894(7) 0.01958(16) Uani d . 1 . .
N N6 -0.32110(15) 0.39514(10) 0.55021(8) 0.02548(19) Uani d . 1 . .
C C1 0.63437(17) 0.17276(12) -0.03615(9) 0.0237(2) Uani d . 1 . .
H H1A 0.5690 0.1433 0.0185 0.028 Uiso calc R 1 . .
C C2 0.78848(17) 0.11197(12) -0.06418(10) 0.0265(2) Uani d . 1 . .
H H2A 0.8263 0.0413 -0.0295 0.032 Uiso calc R 1 . .
C C3 0.88538(17) 0.15913(12) -0.14545(10) 0.0264(2) Uani d . 1 . .
C C4 0.83211(18) 0.26371(12) -0.19913(10) 0.0275(2) Uani d . 1 . .
H H4A 0.8994 0.2941 -0.2527 0.033 Uiso calc R 1 . .
C C5 0.67620(18) 0.32191(11) -0.17115(9) 0.0250(2) Uani d . 1 . .
H H5A 0.6374 0.3911 -0.2073 0.030 Uiso calc R 1 . .
C C6 0.57626(16) 0.27820(11) -0.08939(9) 0.02146(19) Uani d . 1 . .
C C7 0.41298(16) 0.34357(11) -0.06406(9) 0.0225(2) Uani d . 1 . .
H H7A 0.3715 0.4053 -0.1077 0.027 Uiso calc R 1 . .
C C8 0.08764(15) 0.36783(10) 0.10979(8) 0.01926(18) Uani d . 1 . .
C C9 -0.02848(18) 0.25579(12) 0.27750(11) 0.0272(2) Uani d . 1 . .
H H9A -0.1132 0.1856 0.2353 0.033 Uiso calc R 1 . .
H H9B 0.0039 0.2276 0.3479 0.033 Uiso calc R 1 . .
C C10 -0.12334(14) 0.38080(10) 0.29279(9) 0.01908(18) Uani d . 1 . .
C C11 -0.19794(15) 0.42203(10) 0.39393(9) 0.01953(18) Uani d . 1 . .
C C12 -0.19652(16) 0.55221(11) 0.45021(9) 0.0229(2) Uani d . 1 . .
C C13 -0.30832(14) 0.19503(10) 0.43535(9) 0.01922(18) Uani d . 1 . .
C C14 -0.22133(15) 0.11515(11) 0.50272(9) 0.02130(19) Uani d . 1 . .
H H14A -0.1436 0.1523 0.5641 0.026 Uiso calc R 1 . .
C C15 -0.25405(16) -0.02255(11) 0.47558(10) 0.0241(2) Uani d . 1 . .
H H15A -0.1976 -0.0784 0.5194 0.029 Uiso calc R 1 . .
C C16 -0.36970(17) -0.07694(12) 0.38406(11) 0.0257(2) Uani d . 1 . .
H H16A -0.3901 -0.1690 0.3667 0.031 Uiso calc R 1 . .
C C17 -0.45555(17) 0.00539(12) 0.31792(10) 0.0261(2) Uani d . 1 . .
H H17A -0.5334 -0.0318 0.2566 0.031 Uiso calc R 1 . .
C C18 -0.42526(15) 0.14293(12) 0.34325(10) 0.0235(2) Uani d . 1 . .
H H18A -0.4820 0.1988 0.2995 0.028 Uiso calc R 1 . .
H H1N3 -0.095(3) 0.481(2) 0.0777(16) 0.040(5) 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'
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
C8 S1 C9 . . 97.34(5) ?
N6 O1 C12 . . 111.31(8) ?
C7 N1 N2 . . 112.59(9) ?
C8 N2 N1 . . 112.52(9) ?
C8 N3 N4 . . 126.88(9) ?
C8 N3 H1N3 . . 114.7(14) ?
N4 N3 H1N3 . . 111.8(14) ?
C10 N4 N3 . . 118.20(9) ?
N6 N5 C11 . . 115.55(9) ?
N6 N5 C13 . . 117.95(9) ?
C11 N5 C13 . . 126.46(9) ?
N5 N6 O1 . . 104.02(9) ?
C2 C1 C6 . . 120.65(11) ?
C2 C1 H1A . . 119.7 ?
C6 C1 H1A . . 119.7 ?
C1 C2 C3 . . 118.54(11) ?
C1 C2 H2A . . 120.7 ?
C3 C2 H2A . . 120.7 ?
C4 C3 C2 . . 122.18(11) ?
C4 C3 Cl1 . . 118.32(10) ?
C2 C3 Cl1 . . 119.49(10) ?
C5 C4 C3 . . 118.46(11) ?
C5 C4 H4A . . 120.8 ?
C3 C4 H4A . . 120.8 ?
C4 C5 C6 . . 121.04(11) ?
C4 C5 H5A . . 119.5 ?
C6 C5 H5A . . 119.5 ?
C5 C6 C1 . . 119.11(11) ?
C5 C6 C7 . . 118.29(10) ?
C1 C6 C7 . . 122.59(10) ?
N1 C7 C6 . . 121.78(10) ?
N1 C7 H7A . . 119.1 ?
C6 C7 H7A . . 119.1 ?
N2 C8 N3 . . 117.39(9) ?
N2 C8 S1 . . 122.56(8) ?
N3 C8 S1 . . 119.98(8) ?
C10 C9 S1 . . 112.38(8) ?
C10 C9 H9A . . 109.1 ?
S1 C9 H9A . . 109.1 ?
C10 C9 H9B . . 109.1 ?
S1 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.9 ?
N4 C10 C11 . . 115.66(9) ?
N4 C10 C9 . . 123.01(10) ?
C11 C10 C9 . . 121.33(9) ?
N5 C11 C12 . . 105.58(9) ?
N5 C11 C10 . . 125.07(9) ?
C12 C11 C10 . . 129.17(10) ?
O2 C12 O1 . . 120.14(11) ?
O2 C12 C11 . . 136.24(12) ?
O1 C12 C11 . . 103.54(9) ?
C14 C13 C18 . . 122.57(10) ?
C14 C13 N5 . . 119.37(10) ?
C18 C13 N5 . . 118.04(9) ?
C13 C14 C15 . . 117.91(10) ?
C13 C14 H14A . . 121.0 ?
C15 C14 H14A . . 121.0 ?
C16 C15 C14 . . 120.63(10) ?
C16 C15 H15A . . 119.7 ?
C14 C15 H15A . . 119.7 ?
C15 C16 C17 . . 120.33(11) ?
C15 C16 H16A . . 119.8 ?
C17 C16 H16A . . 119.8 ?
C18 C17 C16 . . 120.13(11) ?
C18 C17 H17A . . 119.9 ?
C16 C17 H17A . . 119.9 ?
C13 C18 C17 . . 118.43(10) ?
C13 C18 H18A . . 120.8 ?
C17 C18 H18A . . 120.8 ?
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
Cl1 C3 . 1.7379(13) ?
S1 C8 . 1.7374(10) ?
S1 C9 . 1.8097(12) ?
O1 N6 . 1.3788(13) ?
O1 C12 . 1.4197(15) ?
O2 C12 . 1.2117(14) ?
N1 C7 . 1.2837(15) ?
N1 N2 . 1.3921(13) ?
N2 C8 . 1.3000(14) ?
N3 C8 . 1.3659(14) ?
N3 N4 . 1.3712(13) ?
N3 H1N3 . 0.85(2) ?
N4 C10 . 1.2896(13) ?
N5 N6 . 1.3101(14) ?
N5 C11 . 1.3563(13) ?
N5 C13 . 1.4434(14) ?
C1 C2 . 1.3874(17) ?
C1 C6 . 1.4018(16) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.3940(17) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.3861(19) ?
C4 C5 . 1.3861(18) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.3984(16) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.4607(16) ?
C7 H7A . 0.9300 ?
C9 C10 . 1.5030(15) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.4526(15) ?
C11 C12 . 1.4217(15) ?
C13 C14 . 1.3870(14) ?
C13 C18 . 1.3881(16) ?
C14 C15 . 1.3935(16) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.3836(18) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.3912(18) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.3886(17) ?
C17 H17A . 0.9300 ?
C18 H18A . 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
N3 H1N3 N2 2_565 0.84(2) 2.03(2) 2.8752(14) 178(2) yes
C9 H9A Cl1 2_655 0.97 2.78 3.4904(13) 130 yes
C18 H18A S1 1_455 0.93 2.86 3.6729(12) 147 yes
C17 H17A Cg2 2_555 0.93 2.64 3.5208(15) 158 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
C7 N1 N2 C8 . . . . -175.59(10) ?
C8 N3 N4 C10 . . . . -32.21(16) ?
C11 N5 N6 O1 . . . . -0.32(13) ?
C13 N5 N6 O1 . . . . -178.24(9) ?
C12 O1 N6 N5 . . . . 0.28(12) ?
C6 C1 C2 C3 . . . . 0.77(18) ?
C1 C2 C3 C4 . . . . -0.37(19) ?
C1 C2 C3 Cl1 . . . . -179.55(9) ?
C2 C3 C4 C5 . . . . -0.58(18) ?
Cl1 C3 C4 C5 . . . . 178.61(9) ?
C3 C4 C5 C6 . . . . 1.14(18) ?
C4 C5 C6 C1 . . . . -0.75(17) ?
C4 C5 C6 C7 . . . . -179.85(11) ?
C2 C1 C6 C5 . . . . -0.23(17) ?
C2 C1 C6 C7 . . . . 178.83(11) ?
N2 N1 C7 C6 . . . . -177.30(10) ?
C5 C6 C7 N1 . . . . -172.94(11) ?
C1 C6 C7 N1 . . . . 8.00(18) ?
N1 N2 C8 N3 . . . . -177.81(9) ?
N1 N2 C8 S1 . . . . 5.18(14) ?
N4 N3 C8 N2 . . . . -157.47(11) ?
N4 N3 C8 S1 . . . . 19.62(15) ?
C9 S1 C8 N2 . . . . -165.26(10) ?
C9 S1 C8 N3 . . . . 17.80(10) ?
C8 S1 C9 C10 . . . . -43.84(10) ?
N3 N4 C10 C11 . . . . 177.00(9) ?
N3 N4 C10 C9 . . . . -3.70(16) ?
S1 C9 C10 N4 . . . . 43.07(15) ?
S1 C9 C10 C11 . . . . -137.68(9) ?
N6 N5 C11 C12 . . . . 0.24(13) ?
C13 N5 C11 C12 . . . . 177.95(10) ?
N6 N5 C11 C10 . . . . 175.72(10) ?
C13 N5 C11 C10 . . . . -6.57(17) ?
N4 C10 C11 N5 . . . . 145.80(11) ?
C9 C10 C11 N5 . . . . -33.52(17) ?
N4 C10 C11 C12 . . . . -39.82(16) ?
C9 C10 C11 C12 . . . . 140.87(12) ?
N6 O1 C12 O2 . . . . -177.42(10) ?
N6 O1 C12 C11 . . . . -0.15(12) ?
N5 C11 C12 O2 . . . . 176.55(13) ?
C10 C11 C12 O2 . . . . 1.3(2) ?
N5 C11 C12 O1 . . . . -0.04(11) ?
C10 C11 C12 O1 . . . . -175.28(10) ?
N6 N5 C13 C14 . . . . -63.26(14) ?
C11 N5 C13 C14 . . . . 119.08(12) ?
N6 N5 C13 C18 . . . . 118.73(11) ?
C11 N5 C13 C18 . . . . -58.93(15) ?
C18 C13 C14 C15 . . . . 0.06(16) ?
N5 C13 C14 C15 . . . . -177.86(10) ?
C13 C14 C15 C16 . . . . 0.09(16) ?
C14 C15 C16 C17 . . . . -0.21(17) ?
C15 C16 C17 C18 . . . . 0.17(18) ?
C14 C13 C18 C17 . . . . -0.10(17) ?
N5 C13 C18 C17 . . . . 177.85(10) ?
C16 C17 C18 C13 . . . . -0.01(17) ?
