##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
2-{(E)-[(2Z)-(3-Chloro-1-methyl-2,2-dioxo-3,4-dihydro-
1H-2,1-benzothiazin-4-ylidene)hydrazinylidene]methyl}phenol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H14 Cl N3 O3 S'
_chemical_formula_sum     'C16 H14 Cl N3 O3 S'
_chemical_formula_iupac     'C16 H14 Cl N3 O3 S'
_chemical_formula_weight     363.81
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     7.0973(5)
_cell_length_b     12.0957(7)
_cell_length_c     18.7396(13)
_cell_angle_alpha     90.00
_cell_angle_beta     96.058(4)
_cell_angle_gamma     90.00
_cell_volume     1599.75(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2110
_cell_measurement_theta_min     2.76
_cell_measurement_theta_max     23.68
_cell_measurement_temperature     296(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.19
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.511
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     752
_exptl_absorpt_coefficient_mu     0.390
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min     0.9296
_exptl_absorpt_correction_T_max     0.9732
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     15526
_diffrn_reflns_av_R_equivalents     0.0608
_diffrn_reflns_av_sigmaI/netI     0.0736
_diffrn_reflns_theta_min     2.89
_diffrn_reflns_theta_max     28.32
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     25
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details     ?
_reflns_number_total     3977
_reflns_number_gt     2200
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1378
_refine_ls_R_factor_gt     0.0726
_refine_ls_wR_factor_gt     0.1805
_refine_ls_wR_factor_ref     0.2109
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     3977
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0873P)²+1.6824P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.125
_refine_diff_density_min     -0.382
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)
;
_computing_publication_material
                                'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.51356(17) 0.73641(10) 0.42510(7) 0.0613(4) Uani d . 1 1 . .
    S S1 0.16021(16) 0.83188(8) 0.46237(6) 0.0466(3) Uani d . 1 1 . .
    O O1 -0.0316(4) 0.7950(3) 0.46762(18) 0.0589(9) Uani d . 1 1 . .
    O O2 0.1931(5) 0.9186(2) 0.41328(19) 0.0646(10) Uani d . 1 1 . .
    O O3 0.2121(6) 0.4788(3) 0.27384(18) 0.0632(10) Uani d . 1 1 . .
    N N1 0.2779(5) 0.8598(3) 0.5392(2) 0.0486(9) Uani d . 1 1 . .
    N N2 0.2405(5) 0.5211(3) 0.48831(18) 0.0410(8) Uani d . 1 1 . .
    N N3 0.2244(5) 0.4863(2) 0.41731(18) 0.0409(8) Uani d . 1 1 . .
    C C1 0.2935(6) 0.7761(3) 0.5927(2) 0.0393(9) Uani d . 1 1 . .
    C C2 0.3168(7) 0.8064(4) 0.6654(2) 0.0546(12) Uani d . 1 1 . .
    H H2 0.3185 0.8823 0.6784 0.066 Uiso calc R 1 1 . .
    C C3 0.3368(7) 0.7278(5) 0.7172(3) 0.0625(14) Uani d . 1 1 . .
    H H3 0.3541 0.7496 0.7662 0.075 Uiso calc R 1 1 . .
    C C4 0.3327(7) 0.6172(4) 0.7003(2) 0.0576(12) Uani d . 1 1 . .
    H H4 0.3462 0.5629 0.7371 0.069 Uiso calc R 1 1 . .
    C C5 0.3090(6) 0.5861(4) 0.6295(2) 0.0466(10) Uani d . 1 1 . .
    H H5 0.3059 0.5097 0.6178 0.056 Uiso calc R 1 1 . .
    C C6 0.2894(5) 0.6638(3) 0.5745(2) 0.0349(8) Uani d . 1 1 . .
    C C7 0.2647(5) 0.6248(3) 0.4995(2) 0.0340(8) Uani d . 1 1 . .
    C C8 0.2740(6) 0.7083(3) 0.4402(2) 0.0402(9) Uani d . 1 1 . .
    H H8 0.2059 0.6776 0.3950 0.048 Uiso calc R 1 1 . .
    C C9 0.2063(6) 0.3806(3) 0.4143(2) 0.0399(9) Uani d . 1 1 . .
    H H9 0.2041 0.3408 0.4579 0.048 Uiso calc R 1 1 . .
    C C10 0.1889(5) 0.3193(3) 0.3476(2) 0.0383(9) Uani d . 1 1 . .
    C C11 0.1917(6) 0.3688(3) 0.2807(2) 0.0448(10) Uani d . 1 1 . .
    C C12 0.1740(7) 0.3036(4) 0.2194(3) 0.0570(12) Uani d . 1 1 . .
    H H12 0.1764 0.3368 0.1736 0.068 Uiso calc R 1 1 . .
    C C13 0.1532(7) 0.1921(4) 0.2249(3) 0.0628(14) Uani d . 1 1 . .
    H H13 0.1388 0.1487 0.1824 0.075 Uiso calc R 1 1 . .
    C C14 0.1526(7) 0.1407(4) 0.2903(3) 0.0568(12) Uani d . 1 1 . .
    H H14 0.1393 0.0628 0.2932 0.068 Uiso calc R 1 1 . .
    C C15 0.1715(6) 0.2043(3) 0.3513(3) 0.0464(10) Uani d . 1 1 . .
    H H15 0.1728 0.1695 0.3968 0.056 Uiso calc R 1 1 . .
    C C16 0.3125(10) 0.9768(4) 0.5597(3) 0.0839(18) Uani d . 1 1 . .
    H H16A 0.2108 1.0030 0.5869 0.126 Uiso calc R 1 1 . .
    H H16B 0.3153 1.0217 0.5163 0.126 Uiso calc R 1 1 . .
    H H16C 0.4343 0.9831 0.5893 0.126 Uiso calc R 1 1 . .
    H H3O 0.235(11) 0.509(6) 0.313(4) 0.126 Uiso d . 1 1 . .
_geom_special_details     ?
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 C8 . 1.786(4) ?
    S1 O2 . 1.430(3) ?
    S1 O1 . 1.445(3) ?
    S1 N1 . 1.623(4) ?
    S1 C8 . 1.770(4) ?
    O3 C11 . 1.346(5) ?
    O3 H3O . 0.82(7) ?
    N1 C1 . 1.420(5) ?
    N1 C16 . 1.479(6) ?
    N2 C7 . 1.280(5) ?
    N2 N3 . 1.389(5) ?
    N3 C9 . 1.286(5) ?
    C1 C6 . 1.399(5) ?
    C1 C2 . 1.405(6) ?
    C2 C3 . 1.355(7) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.375(7) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.371(6) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.391(5) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.475(5) ?
    C7 C8 . 1.509(5) ?
    C8 H8 . 1.0000 ?
    C9 C10 . 1.447(5) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.391(6) ?
    C10 C15 . 1.399(5) ?
    C11 C12 . 1.388(6) ?
    C12 C13 . 1.362(7) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.374(7) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.372(6) ?
    C14 H14 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
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
    O2 S1 O1 . . 119.2(2) ?
    O2 S1 N1 . . 108.3(2) ?
    O1 S1 N1 . . 113.8(2) ?
    O2 S1 C8 . . 111.0(2) ?
    O1 S1 C8 . . 102.2(2) ?
    N1 S1 C8 . . 100.35(19) ?
    C11 O3 H3O . . 111(5) ?
    C1 N1 C16 . . 120.1(4) ?
    C1 N1 S1 . . 118.1(3) ?
    C16 N1 S1 . . 119.0(3) ?
    C7 N2 N3 . . 116.8(3) ?
    C9 N3 N2 . . 110.0(3) ?
    C6 C1 C2 . . 119.1(4) ?
    C6 C1 N1 . . 121.5(3) ?
    C2 C1 N1 . . 119.4(4) ?
    C3 C2 C1 . . 120.3(4) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.8 ?
    C2 C3 C4 . . 121.3(4) ?
    C2 C3 H3 . . 119.4 ?
    C4 C3 H3 . . 119.4 ?
    C5 C4 C3 . . 119.1(4) ?
    C5 C4 H4 . . 120.4 ?
    C3 C4 H4 . . 120.4 ?
    C4 C5 C6 . . 121.6(4) ?
    C4 C5 H5 . . 119.2 ?
    C6 C5 H5 . . 119.2 ?
    C5 C6 C1 . . 118.5(4) ?
    C5 C6 C7 . . 118.8(3) ?
    C1 C6 C7 . . 122.7(3) ?
    N2 C7 C6 . . 118.1(3) ?
    N2 C7 C8 . . 123.4(3) ?
    C6 C7 C8 . . 118.5(3) ?
    C7 C8 S1 . . 109.6(3) ?
    C7 C8 Cl1 . . 111.1(3) ?
    S1 C8 Cl1 . . 110.0(2) ?
    C7 C8 H8 . . 108.7 ?
    S1 C8 H8 . . 108.7 ?
    Cl1 C8 H8 . . 108.7 ?
    N3 C9 C10 . . 123.1(4) ?
    N3 C9 H9 . . 118.4 ?
    C10 C9 H9 . . 118.4 ?
    C11 C10 C15 . . 118.8(4) ?
    C11 C10 C9 . . 123.3(4) ?
    C15 C10 C9 . . 117.9(4) ?
    O3 C11 C12 . . 118.9(4) ?
    O3 C11 C10 . . 121.6(4) ?
    C12 C11 C10 . . 119.5(4) ?
    C13 C12 C11 . . 120.1(5) ?
    C13 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C12 C13 C14 . . 121.7(5) ?
    C12 C13 H13 . . 119.2 ?
    C14 C13 H13 . . 119.2 ?
    C15 C14 C13 . . 118.7(4) ?
    C15 C14 H14 . . 120.6 ?
    C13 C14 H14 . . 120.6 ?
    C14 C15 C10 . . 121.2(4) ?
    C14 C15 H15 . . 119.4 ?
    C10 C15 H15 . . 119.4 ?
    N1 C16 H16A . . 109.5 ?
    N1 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    N1 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
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
    O2 S1 N1 C1 . . . . -169.2(3) ?
    O1 S1 N1 C1 . . . . 55.7(4) ?
    C8 S1 N1 C1 . . . . -52.7(3) ?
    O2 S1 N1 C16 . . . . 29.7(5) ?
    O1 S1 N1 C16 . . . . -105.4(4) ?
    C8 S1 N1 C16 . . . . 146.1(4) ?
    C7 N2 N3 C9 . . . . 178.1(4) ?
    C16 N1 C1 C6 . . . . -170.4(4) ?
    S1 N1 C1 C6 . . . . 28.6(5) ?
    C16 N1 C1 C2 . . . . 8.4(6) ?
    S1 N1 C1 C2 . . . . -152.5(3) ?
    C6 C1 C2 C3 . . . . 0.6(7) ?
    N1 C1 C2 C3 . . . . -178.3(4) ?
    C1 C2 C3 C4 . . . . -0.8(8) ?
    C2 C3 C4 C5 . . . . 0.4(8) ?
    C3 C4 C5 C6 . . . . 0.1(7) ?
    C4 C5 C6 C1 . . . . -0.3(6) ?
    C4 C5 C6 C7 . . . . 179.9(4) ?
    C2 C1 C6 C5 . . . . -0.1(6) ?
    N1 C1 C6 C5 . . . . 178.8(4) ?
    C2 C1 C6 C7 . . . . 179.7(4) ?
    N1 C1 C6 C7 . . . . -1.4(6) ?
    N3 N2 C7 C6 . . . . -177.7(3) ?
    N3 N2 C7 C8 . . . . 0.7(6) ?
    C5 C6 C7 N2 . . . . 7.9(5) ?
    C1 C6 C7 N2 . . . . -171.9(4) ?
    C5 C6 C7 C8 . . . . -170.6(4) ?
    C1 C6 C7 C8 . . . . 9.6(6) ?
    N2 C7 C8 S1 . . . . 142.6(3) ?
    C6 C7 C8 S1 . . . . -39.0(4) ?
    N2 C7 C8 Cl1 . . . . -95.6(4) ?
    C6 C7 C8 Cl1 . . . . 82.8(4) ?
    O2 S1 C8 C7 . . . . 170.5(3) ?
    O1 S1 C8 C7 . . . . -61.3(3) ?
    N1 S1 C8 C7 . . . . 56.1(3) ?
    O2 S1 C8 Cl1 . . . . 48.0(3) ?
    O1 S1 C8 Cl1 . . . . 176.2(2) ?
    N1 S1 C8 Cl1 . . . . -66.4(2) ?
    N2 N3 C9 C10 . . . . -179.2(3) ?
    N3 C9 C10 C11 . . . . 0.5(6) ?
    N3 C9 C10 C15 . . . . 179.5(4) ?
    C15 C10 C11 O3 . . . . -178.6(4) ?
    C9 C10 C11 O3 . . . . 0.4(6) ?
    C15 C10 C11 C12 . . . . 1.0(6) ?
    C9 C10 C11 C12 . . . . -180.0(4) ?
    O3 C11 C12 C13 . . . . 180.0(4) ?
    C10 C11 C12 C13 . . . . 0.3(7) ?
    C11 C12 C13 C14 . . . . -1.2(8) ?
    C12 C13 C14 C15 . . . . 0.7(8) ?
    C13 C14 C15 C10 . . . . 0.8(7) ?
    C11 C10 C15 C14 . . . . -1.6(6) ?
    C9 C10 C15 C14 . . . . 179.3(4) ?
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
    O3 H3O N3 . 0.82(7) 1.98(7) 2.682(5) 143(7) yes
    C9 H9 O1 3_566 0.95 2.55 3.394(5) 148.1 yes
data_global
_journal_date_recd_electronic     2011-12-15
_journal_date_accepted     2011-12-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      2
_journal_page_first     o307
_journal_page_last     o307
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536811055978
_journal_coeditor_code     BH2407
_publ_contact_author_name     'Muhammad Shafiq'
_publ_contact_author_address
;
Materials Chemistry Laboratory, Department of Chemistry,
GC University, Lahore-54000, Pakistan
;
_publ_contact_author_email     hafizshafique@hotmail.com
_publ_contact_author_fax     ?
_publ_contact_author_phone      923024487893
_publ_section_title
;\
2-{(E)-[(2Z)-(3-Chloro-1-methyl-2,2-dioxo-3,4-dihydro-\
1H-2,1-benzothiazin-4-ylidene)hydrazinylidene]methyl}phenol
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    "Shafiq, Muhammad" .
;
Materials Chemistry Laboratory
Department of Chemistry
GC University
Lahore 54000
Pakistan
;
    "Khan, Islam Ullah" .
;
Materials Chemistry Laboratory
Department of Chemistry
GC University
Lahore 54000
Pakistan
;
    "Zia-ur-Rehman, Muhammad" .
;
Applied Chemistry Research Center
PCSIR Laboratories Complex
Ferozpur Road
Lahore 54600
Pakistan
;
    "Arshad, Muhammad Nadeem" .
;
Department of Chemistry
University of Gujrat
Gujrat 50781
Pakistan
;
    "Asiri, Abdullah M." .
;
The Center of Excellence for Advanced Materials Research
and Department of Chemistry, Faculty of Science
King Abdul Aziz University
Jeddah, PO Box 80203
Saudi Arabia
;
