4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2<i>H</i>-1,3,4-thiadiazin-5-yl}-3-(4-methoxyphenyl)sydnone
Fun, Hoong-Kun; Loh, Wan-Sin; Nithinchandra; Kalluraya, Balakrishna; Acta Crystallographica Section E 67 (2011) o1175–o1176; doi:10.1107/S1600536811013900

data_2230135
_publ_section_title
;
 4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2<i>H</i>-1,3,4-thiadiazin-5-yl}-3-(4-methoxyphenyl)sydnone
;
_journal_coeditor_code           RZ2581
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1175
_journal_page_last               o1176
_journal_paper_doi               10.1107/S1600536811013900
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H15 Cl N6 O3 S'
_chemical_formula_moiety         'C19 H15 Cl N6 O3 S'
_chemical_formula_sum            'C19 H15 Cl N6 O3 S'
_chemical_formula_weight         442.88
_chemical_name_common
;
4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2<i>H</i>-
1,3,4-thiadiazin-5-yl}-3-(4-methoxyphenyl)sydnone
;
_chemical_name_systematic
;
4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2<i>H</i>-
1,3,4-thiadiazin-5-yl}-3-(4-methoxyphenyl)-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                90.00
_cell_angle_beta                 114.4260(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2322(2)
_cell_length_b                   22.7311(6)
_cell_length_c                   12.9299(3)
_cell_measurement_reflns_used    9060
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      37.56
_cell_measurement_theta_min      3.46
_cell_volume                     1935.37(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      100.00(10)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Bruker SMART APEXII DUO CCD area-detector
;
_diffrn_measurement_method       '\f and \w'
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38523
_diffrn_reflns_theta_full        37.59
_diffrn_reflns_theta_max         37.59
_diffrn_reflns_theta_min         1.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.9370
_exptl_absorpt_correction_T_min  0.8322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2009)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         10172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.4618P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                8764
_reflns_number_total             10172
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            rz2581.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230135
_cod_database_fobs_code          2230135