#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/66/2216625.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_2216625
loop_
_publ_author_name
'Siddiqui, Waseeq Ahmad'
'Ahmad, Saeed'
'Siddiqui, Hamid Latif'
'Tariq, Muhammad Ilyas'
'Parvez, Masood'
_publ_section_title
;
 2-Methyl-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide
;
_journal_coeditor_code           LH2541
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4585
_journal_page_last               o4585
_journal_paper_doi               10.1107/S1600536807054736
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H9 N O3 S'
_chemical_formula_moiety         'C9 H9 N O3 S'
_chemical_formula_sum            'C9 H9 N O3 S'
_chemical_formula_weight         211.23
_chemical_name_systematic
;
2-Methyl-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.778(5)
_cell_length_b                   8.634(6)
_cell_length_c                   15.704(10)
_cell_measurement_reflns_used    2075
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.59
_cell_volume                     919.0(11)
_computing_cell_refinement       'HKL DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SAPI91 (Fan, 1991)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' ω and φ '
_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  0.045
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6478
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.9741
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.338
_refine_ls_abs_structure_details 'Flack (1983), 848 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.14(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.045P)²+0.93P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1245
_reflns_number_gt                1692
_reflns_number_total             2075
_reflns_threshold_expression     'I >2 σ(I)'
_cod_data_source_file            lh2541.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               2216625
_cod_database_fobs_code          2216625
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
S S1 0.38859(14) 0.53500(10) 0.80195(6) 0.0257(2) Uani d . 1
O O1 0.3254(5) 0.2461(3) 1.02285(17) 0.0434(8) Uani d . 1
O O2 0.5943(4) 0.5091(3) 0.78864(16) 0.0334(6) Uani d . 1
O O3 0.2839(4) 0.6302(3) 0.74272(17) 0.0349(7) Uani d . 1
N N1 0.2779(5) 0.3677(3) 0.8062(2) 0.0316(7) Uani d . 1
C C1 0.3568(5) 0.6086(4) 0.9056(2) 0.0242(8) Uani d . 1
C C2 0.3501(6) 0.7667(4) 0.9181(2) 0.0303(9) Uani d . 1
H H2 0.3551 0.8351 0.8708 0.036 Uiso calc R 1
C C3 0.3359(6) 0.8258(5) 1.0006(3) 0.0356(10) Uani d . 1
H H3 0.3313 0.9345 1.0097 0.043 Uiso calc R 1
C C4 0.3285(6) 0.7255(5) 1.0688(3) 0.0369(10) Uani d . 1
H H4 0.3226 0.7658 1.1250 0.044 Uiso calc R 1
C C5 0.3296(5) 0.5657(4) 1.0563(2) 0.0306(9) Uani d . 1
H H5 0.3203 0.4979 1.1038 0.037 Uiso calc R 1
C C6 0.3441(5) 0.5051(4) 0.9746(2) 0.0247(8) Uani d . 1
C C7 0.3406(6) 0.3334(4) 0.9631(2) 0.0287(8) Uani d . 1
C C8 0.3629(7) 0.2676(4) 0.8739(2) 0.0344(9) Uani d . 1
H H8A 0.5049 0.2517 0.8620 0.041 Uiso calc R 1
H H8B 0.2977 0.1651 0.8717 0.041 Uiso calc R 1
C C9 0.0596(6) 0.3734(6) 0.8058(3) 0.0479(11) Uani d . 1
H H9A 0.0069 0.2681 0.8008 0.057 Uiso calc R 1
H H9B 0.0145 0.4357 0.7574 0.057 Uiso calc R 1
H H9C 0.0127 0.4202 0.8589 0.057 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 0.0278(4) 0.0258(4) 0.0235(4) -0.0017(4) 0.0001(4) 0.0021(4)
O1 0.064(2) 0.0348(15) 0.0317(15) 0.0023(14) 0.0011(14) 0.0103(13)
O2 0.0234(13) 0.0411(15) 0.0358(14) -0.0007(12) 0.0056(12) -0.0005(11)
O3 0.0352(16) 0.0381(15) 0.0313(14) 0.0037(12) -0.0035(12) 0.0094(12)
N1 0.0404(19) 0.0290(15) 0.0254(16) -0.0083(13) 0.0017(16) -0.0002(15)
C1 0.0183(19) 0.0256(17) 0.0288(18) -0.0021(15) 0.0017(15) -0.0007(14)
C2 0.025(2) 0.029(2) 0.037(2) -0.0005(16) -0.0019(17) -0.0006(16)
C3 0.024(2) 0.034(2) 0.049(3) 0.0015(16) -0.0018(18) -0.0111(19)
C4 0.027(2) 0.047(3) 0.036(2) 0.0051(18) -0.0013(17) -0.0170(19)
C5 0.028(2) 0.040(2) 0.0242(18) 0.0044(16) 0.0009(15) -0.0044(15)
C6 0.0243(19) 0.0281(19) 0.0218(16) 0.0013(13) -0.0004(15) -0.0021(13)
C7 0.033(2) 0.0288(19) 0.0246(18) 0.0029(16) 0.0000(16) 0.0040(15)
C8 0.055(3) 0.0204(17) 0.0274(18) 0.0010(19) 0.0067(19) 0.0033(14)
C9 0.040(3) 0.067(3) 0.037(2) -0.027(2) -0.003(2) 0.005(2)
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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O3 118.66(16)
O2 S1 N1 108.48(17)
O3 S1 N1 107.92(18)
O2 S1 C1 108.16(16)
O3 S1 C1 109.45(17)
N1 S1 C1 103.05(16)
C9 N1 C8 114.2(3)
C9 N1 S1 115.5(3)
C8 N1 S1 111.5(3)
C2 C1 C6 121.1(3)
C2 C1 S1 119.6(3)
C6 C1 S1 119.3(3)
C1 C2 C3 119.8(4)
C1 C2 H2 120.1
C3 C2 H2 120.1
C4 C3 C2 119.6(4)
C4 C3 H3 120.2
C2 C3 H3 120.2
C3 C4 C5 120.9(4)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 120.2(4)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C1 118.5(3)
C5 C6 C7 118.9(3)
C1 C6 C7 122.6(3)
O1 C7 C6 121.8(3)
O1 C7 C8 119.4(3)
C6 C7 C8 118.7(3)
N1 C8 C7 113.8(3)
N1 C8 H8A 108.8
C7 C8 H8A 108.8
N1 C8 H8B 108.8
C7 C8 H8B 108.8
H8A C8 H8B 107.7
N1 C9 H9A 109.5
N1 C9 H9B 109.5
H9A C9 H9B 109.5
N1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.428(3)
S1 O3 1.430(3)
S1 N1 1.629(3)
S1 C1 1.760(4)
O1 C7 1.207(4)
N1 C9 1.481(5)
N1 C8 1.487(5)
C1 C2 1.380(5)
C1 C6 1.407(5)
C2 C3 1.395(5)
C2 H2 0.9500
C3 C4 1.379(6)
C3 H3 0.9500
C4 C5 1.393(6)
C4 H4 0.9500
C5 C6 1.390(5)
C5 H5 0.9500
C6 C7 1.494(5)
C7 C8 1.519(5)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
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
C5 H5 O3 2_565 0.95 2.55 3.467(5) 163.5
C8 H8A O3 4_646 0.99 2.42 3.240(5) 139.8
C9 H9A O3 4_546 0.98 2.40 3.226(5) 141.4
C8 H8A O2 . 0.99 2.58 2.933(5) 101.2
C9 H9B O3 . 0.98 2.49 2.865(5) 102.3
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
O2 S1 N1 C9 -170.5(3)
O3 S1 N1 C9 -40.7(3)
C1 S1 N1 C9 75.0(3)
O2 S1 N1 C8 57.0(3)
O3 S1 N1 C8 -173.3(2)
C1 S1 N1 C8 -57.5(3)
O2 S1 C1 C2 93.8(3)
O3 S1 C1 C2 -36.9(3)
N1 S1 C1 C2 -151.5(3)
O2 S1 C1 C6 -84.5(3)
O3 S1 C1 C6 144.9(3)
N1 S1 C1 C6 30.3(3)
C6 C1 C2 C3 1.7(6)
S1 C1 C2 C3 -176.5(3)
C1 C2 C3 C4 -0.1(6)
C2 C3 C4 C5 -1.8(6)
C3 C4 C5 C6 2.0(6)
C4 C5 C6 C1 -0.3(5)
C4 C5 C6 C7 -178.7(3)
C2 C1 C6 C5 -1.6(5)
S1 C1 C6 C5 176.6(3)
C2 C1 C6 C7 176.8(3)
S1 C1 C6 C7 -5.0(5)
C5 C6 C7 O1 0.0(6)
C1 C6 C7 O1 -178.3(4)
C5 C6 C7 C8 -178.2(3)
C1 C6 C7 C8 3.4(6)
C9 N1 C8 C7 -70.9(5)
S1 N1 C8 C7 62.3(4)
O1 C7 C8 N1 149.6(4)
C6 C7 C8 N1 -32.2(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5918189
