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###        Electronic paper (Acta Crystallographica Section E)             ###
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#                                                                            #
# 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 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     ?
_journal_date_recd_electronic     2008-01-13
_journal_date_accepted     2008-01-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      3
_journal_page_first     o557
_journal_page_last     o557
_journal_paper_category     QO
_journal_coeditor_code     BQ2063
_publ_contact_author
;Muhammad Nawaz Tahir
University of Sarodha
Department of Physics
Sarodha
Pakistan
;
_publ_contact_author_email     dmntahir_uos@yahoo.com
_publ_contact_author_fax     '0092 48 32 22 121'
_publ_contact_author_phone     '0092 48 92 30 170'
_publ_section_title
;
1-Methyl-1<i>H</i>-2,1-benzothiazin-4(3<i>H</i>)-one 2,2-dioxide
;
loop_
    _publ_author_name
    _publ_author_address
    'Tahir, M. Nawaz'
;
University of Sargodha
Department of Physics
Sargodha
Pakistan
;
    'Muhammad Shafiq'
;
Government College University
Department of Chemistry
Lahore
Pakistan
;
    'Islam Ullah Khan'
;
Government College University
Department of Chemistry
Lahore
Pakistan
;
    'Waseeq Ahmad Siddiqui'
;
University of Sargodha
Department of Chemistry
Sargodha
Pakistan
;
    'Muhammad Nadeem Arshad'
;
Government College University
Department of Chemistry
Lahore
Pakistan
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-Methyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H9 N O3 S'
_chemical_formula_sum     'C9 H9 N O3 S'
_chemical_formula_iupac     'C9 H9  N O3 S'
_chemical_formula_weight     211.23
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.4553(4)
_cell_length_b     8.5437(4)
_cell_length_c     8.7097(4)
_cell_angle_alpha     67.691(2)
_cell_angle_beta     70.467(2)
_cell_angle_gamma     66.327(2)
_cell_volume     459.09(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1678
_cell_measurement_theta_min     2.59
_cell_measurement_theta_max     25.94
_cell_measurement_temperature     296(2)
_exptl_crystal_description     prismatic
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.528
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     220
_exptl_absorpt_coefficient_mu     0.330
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min     0.952
_exptl_absorpt_correction_T_max     0.971
_exptl_special_details     ' '
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     'MoK\a radiation'
_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     \w
_diffrn_detector_area_resol_mean     7.50
_diffrn_reflns_number     7205
_diffrn_reflns_av_R_equivalents     0.0195
_diffrn_reflns_av_sigmaI/netI     0.0147
_diffrn_reflns_theta_min     2.59
_diffrn_reflns_theta_max     25.94
_diffrn_reflns_theta_full     25.94
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1787
_reflns_number_gt     1678
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0340
_refine_ls_R_factor_gt     0.0319
_refine_ls_wR_factor_gt     0.0915
_refine_ls_wR_factor_ref     0.0945
_refine_ls_goodness_of_fit_ref     1.086
_refine_ls_restrained_S_all     1.086
_refine_ls_number_reflns     1678
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.1411P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.218
_refine_diff_density_min     -0.419
_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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'APEX2 (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, 2003)'
_computing_publication_material
                                'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)'
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
    S S1 0.18773(6) 0.94371(5) 0.15987(5) 0.03811(16) Uani d . 1 . .
    O O1 -0.02000(18) 0.95817(16) 0.20416(15) 0.0472(3) Uani d . 1 . .
    O O2 0.2454(2) 1.09673(18) 0.05037(17) 0.0618(4) Uani d . 1 . .
    O O3 0.3153(2) 0.46358(19) 0.16958(19) 0.0641(4) Uani d . 1 . .
    N N1 0.2759(2) 0.87608(18) 0.33158(17) 0.0410(3) Uani d . 1 . .
    C C1 0.2522(2) 0.71412(19) 0.45108(18) 0.0327(3) Uani d . 1 . .
    C C2 0.2208(3) 0.6907(2) 0.6241(2) 0.0447(4) Uani d . 1 . .
    H H2 0.2151 0.7814 0.6616 0.054 Uiso calc R 1 . .
    C C3 0.1982(3) 0.5318(3) 0.7405(2) 0.0540(5) Uani d . 1 . .
    H H3 0.1782 0.5166 0.8559 0.065 Uiso calc R 1 . .
    C C4 0.2048(3) 0.3964(3) 0.6881(2) 0.0548(5) Uani d . 1 . .
    H H4 0.1883 0.2908 0.7672 0.066 Uiso calc R 1 . .
    C C5 0.2359(2) 0.4185(2) 0.5186(2) 0.0462(4) Uani d . 1 . .
    H H5 0.2398 0.3270 0.4833 0.055 Uiso calc R 1 . .
    C C6 0.2618(2) 0.57543(19) 0.39688(19) 0.0341(3) Uani d . 1 . .
    C C7 0.2997(2) 0.5863(2) 0.2155(2) 0.0399(4) Uani d . 1 . .
    C C8 0.3241(3) 0.7571(2) 0.0823(2) 0.0434(4) Uani d . 1 . .
    H H8A 0.2785 0.7728 -0.0162 0.052 Uiso calc R 1 . .
    H H8B 0.4650 0.7481 0.0465 0.052 Uiso calc R 1 . .
    C C9 0.3194(3) 1.0018(3) 0.3773(3) 0.0555(5) Uani d . 1 . .
    H H9A 0.3301 1.1026 0.2801 0.083 Uiso calc R 1 . .
    H H9B 0.4436 0.9450 0.4149 0.083 Uiso calc R 1 . .
    H H9C 0.2133 1.0409 0.4671 0.083 Uiso calc R 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 0.0511(3) 0.0305(2) 0.0313(2) -0.01201(17) -0.01384(17) -0.00395(16)
    O1 0.0486(7) 0.0447(7) 0.0460(7) -0.0040(5) -0.0179(5) -0.0152(5)
    O2 0.0921(11) 0.0419(7) 0.0480(7) -0.0301(7) -0.0247(7) 0.0087(6)
    O3 0.0813(10) 0.0563(8) 0.0664(9) -0.0287(7) 0.0007(7) -0.0364(7)
    N1 0.0614(9) 0.0327(7) 0.0371(7) -0.0211(6) -0.0205(6) -0.0033(6)
    C1 0.0317(7) 0.0311(7) 0.0322(7) -0.0082(6) -0.0092(6) -0.0055(6)
    C2 0.0462(9) 0.0493(10) 0.0356(8) -0.0100(7) -0.0121(7) -0.0113(7)
    C3 0.0454(10) 0.0683(13) 0.0313(8) -0.0154(9) -0.0091(7) 0.0017(8)
    C4 0.0474(10) 0.0477(10) 0.0511(11) -0.0196(8) -0.0126(8) 0.0116(8)
    C5 0.0414(9) 0.0330(8) 0.0580(11) -0.0132(7) -0.0129(8) -0.0029(7)
    C6 0.0304(7) 0.0293(7) 0.0386(8) -0.0084(6) -0.0068(6) -0.0072(6)
    C7 0.0364(8) 0.0391(8) 0.0458(9) -0.0101(6) -0.0046(6) -0.0193(7)
    C8 0.0500(9) 0.0451(9) 0.0317(8) -0.0113(7) -0.0055(7) -0.0141(7)
    C9 0.0770(13) 0.0443(10) 0.0624(11) -0.0274(9) -0.0267(10) -0.0143(8)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 . 1.4262(13) y
    S1 O1 . 1.4302(13) y
    S1 N1 . 1.6429(13) y
    S1 C8 . 1.7574(17) y
    O3 C7 . 1.209(2) n
    N1 C1 . 1.4175(18) n
    N1 C9 . 1.452(2) n
    C1 C2 . 1.393(2) n
    C1 C6 . 1.402(2) n
    C2 C3 . 1.387(2) n
    C2 H2 . 0.9300 n
    C3 C4 . 1.375(3) n
    C3 H3 . 0.9300 n
    C4 C5 . 1.365(3) n
    C4 H4 . 0.9300 n
    C5 C6 . 1.397(2) n
    C5 H5 . 0.9300 n
    C6 C7 . 1.482(2) n
    C7 C8 . 1.515(2) n
    C8 H8A . 0.9700 n
    C8 H8B . 0.9700 n
    C9 H9A . 0.9600 n
    C9 H9B . 0.9600 n
    C9 H9C . 0.9600 n
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 . . 118.32(8) y
    O2 S1 N1 . . 107.31(8) y
    O1 S1 N1 . . 110.55(7) y
    O2 S1 C8 . . 111.61(9) y
    O1 S1 C8 . . 107.95(8) y
    N1 S1 C8 . . 99.47(8) y
    C1 N1 C9 . . 121.70(14) n
    C1 N1 S1 . . 116.58(10) n
    C9 N1 S1 . . 119.32(12) n
    C2 C1 C6 . . 119.27(14) n
    C2 C1 N1 . . 120.09(14) n
    C6 C1 N1 . . 120.63(13) n
    C3 C2 C1 . . 119.87(17) n
    C3 C2 H2 . . 120.1 n
    C1 C2 H2 . . 120.1 n
    C4 C3 C2 . . 121.05(17) n
    C4 C3 H3 . . 119.5 n
    C2 C3 H3 . . 119.5 n
    C5 C4 C3 . . 119.31(16) n
    C5 C4 H4 . . 120.3 n
    C3 C4 H4 . . 120.3 n
    C4 C5 C6 . . 121.56(17) n
    C4 C5 H5 . . 119.2 n
    C6 C5 H5 . . 119.2 n
    C5 C6 C1 . . 118.92(15) n
    C5 C6 C7 . . 117.93(14) n
    C1 C6 C7 . . 123.14(14) n
    O3 C7 C6 . . 122.71(16) y
    O3 C7 C8 . . 118.80(15) y
    C6 C7 C8 . . 118.48(13) n
    C7 C8 S1 . . 111.72(11) n
    C7 C8 H8A . . 109.3 n
    S1 C8 H8A . . 109.3 n
    C7 C8 H8B . . 109.3 n
    S1 C8 H8B . . 109.3 n
    H8A C8 H8B . . 107.9 n
    N1 C9 H9A . . 109.5 n
    N1 C9 H9B . . 109.5 n
    H9A C9 H9B . . 109.5 n
    N1 C9 H9C . . 109.5 n
    H9A C9 H9C . . 109.5 n
    H9B C9 H9C . . 109.5 n
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 . . . . -174.04(12) n
    O1 S1 N1 C1 . . . . 55.60(13) n
    C8 S1 N1 C1 . . . . -57.74(13) n
    O2 S1 N1 C9 . . . . 23.23(18) n
    O1 S1 N1 C9 . . . . -107.13(15) n
    C8 S1 N1 C9 . . . . 139.53(15) n
    C9 N1 C1 C2 . . . . 15.9(2) n
    S1 N1 C1 C2 . . . . -146.39(13) n
    C9 N1 C1 C6 . . . . -163.48(16) n
    S1 N1 C1 C6 . . . . 34.24(18) n
    C6 C1 C2 C3 . . . . -0.5(2) n
    N1 C1 C2 C3 . . . . -179.84(14) n
    C1 C2 C3 C4 . . . . -0.4(3) n
    C2 C3 C4 C5 . . . . 0.6(3) n
    C3 C4 C5 C6 . . . . 0.2(3) n
    C4 C5 C6 C1 . . . . -1.1(2) n
    C4 C5 C6 C7 . . . . 178.55(15) n
    C2 C1 C6 C5 . . . . 1.2(2) n
    N1 C1 C6 C5 . . . . -179.41(14) n
    C2 C1 C6 C7 . . . . -178.43(14) n
    N1 C1 C6 C7 . . . . 0.9(2) n
    C5 C6 C7 O3 . . . . -2.5(2) n
    C1 C6 C7 O3 . . . . 177.15(16) n
    C5 C6 C7 C8 . . . . 178.83(14) n
    C1 C6 C7 C8 . . . . -1.5(2) n
    O3 C7 C8 S1 . . . . 151.98(15) n
    C6 C7 C8 S1 . . . . -29.30(18) n
    O2 S1 C8 C7 . . . . 166.75(12) n
    O1 S1 C8 C7 . . . . -61.58(13) n
    N1 S1 C8 C7 . . . . 53.77(13) n
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
    C2 H2 O1 2_576 0.93 2.58 3.432(2) 152
    C4 H4 O2 1_546 0.93 2.46 3.238(3) 142
    C9 H9A O2 1_555 0.96 2.31 2.830(3) 113