##############################################################################
#                                                                            #
# 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     SHELXL-97
_chemical_name_systematic
;
2-(3,5-Dimethyl-1,1-dioxo-2<i>H</i>-1\l^6^,2,6-thiadiazin-4-yl)benzoic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H12 N2 O4 S'
_chemical_formula_sum     'C12 H12 N2 O4 S'
_chemical_formula_iupac     'C12 H12 N2 O4 S'
_chemical_formula_weight     280.30
_chemical_melting_point     523
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     10.5048(14)
_cell_length_b     10.4254(13)
_cell_length_c     11.1294(14)
_cell_angle_alpha     90.00
_cell_angle_beta     92.772(4)
_cell_angle_gamma     90.00
_cell_volume     1217.4(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5724
_cell_measurement_theta_min     2.60
_cell_measurement_theta_max     28.41
_cell_measurement_temperature     173(2)
_exptl_crystal_description     0
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.529
_exptl_crystal_density_meas     0
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     584
_exptl_absorpt_coefficient_mu     0.278
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2006)'
_exptl_absorpt_correction_T_min     0.9362
_exptl_absorpt_correction_T_max     0.9516
_exptl_special_details     ?
_diffrn_ambient_temperature     173(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 DUO APEXII'
_diffrn_measurement_method     '0.5\% \f scans and \w scans'
_diffrn_reflns_number     5724
_diffrn_reflns_av_R_equivalents     0.0204
_diffrn_reflns_av_sigmaI/netI     0.0288
_diffrn_reflns_theta_min     2.60
_diffrn_reflns_theta_max     28.41
_diffrn_reflns_theta_full     28.41
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     3030
_reflns_number_gt     2573
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0455
_refine_ls_R_factor_gt     0.0378
_refine_ls_wR_factor_gt     0.0978
_refine_ls_wR_factor_ref     0.1026
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_restrained_S_all     1.052
_refine_ls_number_reflns     3030
_refine_ls_number_parameters     187
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.4988P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.369
_refine_diff_density_min     -0.420
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     0
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'
_computing_data_collection     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'SAINT (Bruker, 2006)'
_computing_data_reduction     'SAINT (Bruker, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'OLEX2 (Dolomanov <i>et al.</i>, 2009)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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
    S S1 0.98957(3) 0.13712(4) 0.12970(3) 0.02250(12) Uani d . 1 1 . .
    O O1 1.01274(12) 0.00736(13) 0.16838(11) 0.0344(3) Uani d . 1 1 . .
    O O2 1.09339(11) 0.20118(15) 0.07866(12) 0.0395(3) Uani d . 1 1 . .
    O O3 0.39308(11) 0.41036(12) 0.06653(11) 0.0311(3) Uani d D 1 1 . .
    O O4 0.60472(11) 0.39428(13) 0.08005(13) 0.0353(3) Uani d D 1 1 . .
    N N1 0.87045(12) 0.13786(13) 0.02772(11) 0.0231(3) Uani d D 1 1 . .
    N N2 0.93605(12) 0.21970(13) 0.23740(12) 0.0241(3) Uani d . 1 1 . .
    C C1 0.65248(16) 0.09799(18) -0.03955(14) 0.0285(3) Uani d . 1 1 . .
    H H1A 0.5677 0.0883 -0.0076 0.043 Uiso calc R 1 1 . .
    H H1B 0.6784 0.0168 -0.0754 0.043 Uiso calc R 1 1 . .
    H H1C 0.6500 0.1653 -0.1010 0.043 Uiso calc R 1 1 . .
    C C2 0.74610(14) 0.13394(14) 0.06012(13) 0.0201(3) Uani d . 1 1 . .
    C C3 0.71616(13) 0.16832(14) 0.17403(13) 0.0192(3) Uani d . 1 1 . .
    C C4 0.81280(14) 0.22158(14) 0.25478(13) 0.0208(3) Uani d . 1 1 . .
    C C5 0.77422(16) 0.29238(17) 0.36412(15) 0.0293(4) Uani d . 1 1 . .
    H H5A 0.8483 0.3374 0.4007 0.044 Uiso calc R 1 1 . .
    H H5B 0.7416 0.2314 0.4222 0.044 Uiso calc R 1 1 . .
    H H5C 0.7076 0.3547 0.3412 0.044 Uiso calc R 1 1 . .
    C C6 0.58294(14) 0.15746(14) 0.21603(13) 0.0204(3) Uani d . 1 1 . .
    C C7 0.48160(14) 0.24135(14) 0.18462(13) 0.0206(3) Uani d . 1 1 . .
    C C8 0.36101(15) 0.21905(16) 0.22911(14) 0.0252(3) Uani d . 1 1 . .
    H H8 0.2925 0.2749 0.2067 0.030 Uiso calc R 1 1 . .
    C C9 0.34023(16) 0.11711(17) 0.30514(15) 0.0292(4) Uani d . 1 1 . .
    H H9 0.2581 0.1035 0.3349 0.035 Uiso calc R 1 1 . .
    C C10 0.43933(16) 0.03505(17) 0.33774(15) 0.0296(4) Uani d . 1 1 . .
    H H10 0.4257 -0.0349 0.3903 0.036 Uiso calc R 1 1 . .
    C C11 0.55916(16) 0.05546(15) 0.29322(14) 0.0263(3) Uani d . 1 1 . .
    H H11 0.6267 -0.0015 0.3159 0.032 Uiso calc R 1 1 . .
    C C12 0.49362(14) 0.35576(14) 0.10521(14) 0.0217(3) Uani d . 1 1 . .
    H H4 0.606(4) 0.469(2) 0.028(3) 0.030(16) Uiso d PD 0.52(8) 1 . .
    H H3 0.406(6) 0.491(3) 0.025(5) 0.06(2) Uiso d PD 0.48(8) 1 . .
    H H1 0.892(2) 0.113(2) -0.0528(8) 0.047(6) Uiso d D 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.01708(18) 0.0281(2) 0.02257(19) 0.00231(14) 0.00382(13) -0.00124(14)
    O1 0.0401(7) 0.0339(7) 0.0292(6) 0.0161(6) 0.0017(5) 0.0019(5)
    O2 0.0237(6) 0.0582(9) 0.0374(7) -0.0106(6) 0.0105(5) -0.0040(6)
    O3 0.0259(6) 0.0294(6) 0.0376(7) 0.0023(5) -0.0030(5) 0.0086(5)
    O4 0.0255(6) 0.0308(6) 0.0503(8) 0.0038(5) 0.0102(5) 0.0165(6)
    N1 0.0207(6) 0.0306(7) 0.0182(6) 0.0028(5) 0.0029(5) -0.0019(5)
    N2 0.0201(6) 0.0278(7) 0.0246(6) 0.0012(5) 0.0017(5) -0.0048(5)
    C1 0.0275(8) 0.0347(9) 0.0231(7) -0.0019(7) -0.0012(6) -0.0041(7)
    C2 0.0201(7) 0.0183(7) 0.0219(7) 0.0013(5) 0.0018(5) 0.0012(6)
    C3 0.0182(6) 0.0178(6) 0.0218(7) 0.0022(5) 0.0030(5) 0.0010(5)
    C4 0.0228(7) 0.0193(7) 0.0204(6) 0.0026(6) 0.0026(5) 0.0000(5)
    C5 0.0275(8) 0.0350(9) 0.0256(7) 0.0028(7) 0.0024(6) -0.0096(7)
    C6 0.0196(7) 0.0211(7) 0.0207(6) -0.0005(6) 0.0035(5) -0.0006(5)
    C7 0.0191(7) 0.0206(7) 0.0222(7) -0.0010(6) 0.0027(5) -0.0011(6)
    C8 0.0191(7) 0.0281(8) 0.0285(7) 0.0005(6) 0.0031(6) -0.0019(6)
    C9 0.0242(8) 0.0326(9) 0.0313(8) -0.0066(7) 0.0081(6) -0.0011(7)
    C10 0.0338(9) 0.0278(8) 0.0279(8) -0.0048(7) 0.0071(6) 0.0039(7)
    C11 0.0277(8) 0.0233(8) 0.0281(7) 0.0024(6) 0.0038(6) 0.0036(6)
    C12 0.0212(7) 0.0202(7) 0.0236(7) 0.0012(6) 0.0016(5) -0.0014(6)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    S1 O2 . 1.4206(12) ?
    S1 O1 . 1.4368(13) ?
    S1 N2 . 1.5998(13) ?
    S1 N1 . 1.6483(13) ?
    O3 C12 . 1.2573(19) ?
    O3 H3 . 0.9699(10) ?
    O4 C12 . 1.2781(18) ?
    O4 H4 . 0.9699(10) ?
    N1 C2 . 1.3724(19) ?
    N1 H1 . 0.9698(10) ?
    N2 C4 . 1.3185(19) ?
    C1 C2 . 1.494(2) ?
    C1 H1A . 0.9800 ?
    C1 H1B . 0.9800 ?
    C1 H1C . 0.9800 ?
    C2 C3 . 1.369(2) ?
    C3 C4 . 1.435(2) ?
    C3 C6 . 1.5011(19) ?
    C4 C5 . 1.496(2) ?
    C5 H5A . 0.9800 ?
    C5 H5B . 0.9800 ?
    C5 H5C . 0.9800 ?
    C6 C11 . 1.397(2) ?
    C6 C7 . 1.409(2) ?
    C7 C8 . 1.402(2) ?
    C7 C12 . 1.493(2) ?
    C8 C9 . 1.382(2) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.382(2) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.391(2) ?
    C10 H10 . 0.9500 ?
    C11 H11 . 0.9500 ?
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 . . 116.12(8) ?
    O2 S1 N2 . . 110.55(8) ?
    O1 S1 N2 . . 110.05(7) ?
    O2 S1 N1 . . 107.12(8) ?
    O1 S1 N1 . . 108.82(8) ?
    N2 S1 N1 . . 103.34(7) ?
    C12 O3 H3 . . 115(4) ?
    C12 O4 H4 . . 115(2) ?
    C2 N1 S1 . . 121.29(10) ?
    C2 N1 H1 . . 120.0(14) ?
    S1 N1 H1 . . 115.7(14) ?
    C4 N2 S1 . . 120.07(11) ?
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C3 C2 N1 . . 119.99(14) ?
    C3 C2 C1 . . 125.51(14) ?
    N1 C2 C1 . . 114.40(13) ?
    C2 C3 C4 . . 119.62(13) ?
    C2 C3 C6 . . 121.88(13) ?
    C4 C3 C6 . . 118.44(12) ?
    N2 C4 C3 . . 124.92(13) ?
    N2 C4 C5 . . 115.67(13) ?
    C3 C4 C5 . . 119.29(13) ?
    C4 C5 H5A . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C4 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C11 C6 C7 . . 118.02(13) ?
    C11 C6 C3 . . 116.49(13) ?
    C7 C6 C3 . . 125.49(13) ?
    C8 C7 C6 . . 119.63(14) ?
    C8 C7 C12 . . 116.44(13) ?
    C6 C7 C12 . . 123.94(13) ?
    C9 C8 C7 . . 121.06(15) ?
    C9 C8 H8 . . 119.5 ?
    C7 C8 H8 . . 119.5 ?
    C10 C9 C8 . . 119.82(15) ?
    C10 C9 H9 . . 120.1 ?
    C8 C9 H9 . . 120.1 ?
    C9 C10 C11 . . 119.65(15) ?
    C9 C10 H10 . . 120.2 ?
    C11 C10 H10 . . 120.2 ?
    C10 C11 C6 . . 121.82(15) ?
    C10 C11 H11 . . 119.1 ?
    C6 C11 H11 . . 119.1 ?
    O3 C12 O4 . . 122.93(14) ?
    O3 C12 C7 . . 118.07(13) ?
    O4 C12 C7 . . 119.00(13) ?
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 C2 . . . . -152.60(12) ?
    O1 S1 N1 C2 . . . . 81.12(13) ?
    N2 S1 N1 C2 . . . . -35.82(14) ?
    O2 S1 N2 C4 . . . . 143.83(13) ?
    O1 S1 N2 C4 . . . . -86.58(14) ?
    N1 S1 N2 C4 . . . . 29.49(14) ?
    S1 N1 C2 C3 . . . . 20.0(2) ?
    S1 N1 C2 C1 . . . . -163.46(12) ?
    N1 C2 C3 C4 . . . . 6.8(2) ?
    C1 C2 C3 C4 . . . . -169.34(15) ?
    N1 C2 C3 C6 . . . . -175.96(13) ?
    C1 C2 C3 C6 . . . . 7.9(2) ?
    S1 N2 C4 C3 . . . . -9.0(2) ?
    S1 N2 C4 C5 . . . . 174.88(12) ?
    C2 C3 C4 N2 . . . . -13.2(2) ?
    C6 C3 C4 N2 . . . . 169.49(14) ?
    C2 C3 C4 C5 . . . . 162.84(15) ?
    C6 C3 C4 C5 . . . . -14.5(2) ?
    C2 C3 C6 C11 . . . . 104.52(17) ?
    C4 C3 C6 C11 . . . . -78.20(18) ?
    C2 C3 C6 C7 . . . . -75.8(2) ?
    C4 C3 C6 C7 . . . . 101.44(18) ?
    C11 C6 C7 C8 . . . . -1.2(2) ?
    C3 C6 C7 C8 . . . . 179.14(14) ?
    C11 C6 C7 C12 . . . . 178.69(14) ?
    C3 C6 C7 C12 . . . . -0.9(2) ?
    C6 C7 C8 C9 . . . . 1.1(2) ?
    C12 C7 C8 C9 . . . . -178.81(15) ?
    C7 C8 C9 C10 . . . . -0.3(3) ?
    C8 C9 C10 C11 . . . . -0.3(3) ?
    C9 C10 C11 C6 . . . . 0.2(3) ?
    C7 C6 C11 C10 . . . . 0.6(2) ?
    C3 C6 C11 C10 . . . . -179.72(14) ?
    C8 C7 C12 O3 . . . . -12.3(2) ?
    C6 C7 C12 O3 . . . . 167.81(15) ?
    C8 C7 C12 O4 . . . . 167.35(15) ?
    C6 C7 C12 O4 . . . . -12.6(2) ?
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
    N1 H1 O1 3_755 0.970(12) 2.087(17) 2.9699(18) 150.5(15)
    O4 H4 O3 3_665 0.97(3) 1.64(3) 2.6103(19) 177(3)
    O3 H3 O4 3_665 0.97(3) 1.67(3) 2.6103(19) 161(5)
data_global
_journal_date_recd_electronic     2012-07-23
_journal_date_accepted     2012-08-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue     10
_journal_page_first     o2859
_journal_page_last     o2859
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812037026
_journal_coeditor_code     LH5507
_publ_contact_author_name     'Glenn E.M. Maguire'
_publ_contact_author_address
;
School of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
;
_publ_contact_author_email     maguireg@ukzn.ac.za
_publ_contact_author_fax     '0312603091'
_publ_contact_author_phone     '0312601113'
_publ_section_title
;
2-(3,5-Dimethyl-1,1-dioxo-2<i>H</i>-1\l^6^,2,6-thiadiazin-4-yl)benzoic acid
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Bhatt, Nilay' .
;
Chemistry Department, JJT University, Rajasthan, India
;
    'Bhatt, Pralav' .
;
School of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
;
    'Govender, Thavendran' .
;
School of Pharmacology, University of KwaZulu Natal, Westville Campus,
Private Bag X54001, South Africa
;
    'Kruger, Hendrik G.' .
;
School of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
;
    'Maguire, Glenn E. M.' .
;
School of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
;