#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225841.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_2225841
loop_
_publ_author_name
'Gul, Salman'
'Siddiqui, Hamid Latif'
'Ahmad, Matloob'
'Parvez, Masood'
_publ_section_title
;
 (4-Hydroxy-1,1-dioxo-2H-1,2-benzothiazin-3-yl)(3-methoxyphenyl)methanone
;
_journal_coeditor_code           FL2296
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1021
_journal_paper_doi               10.1107/S1600536810011827
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H13 N O5 S'
_chemical_formula_moiety         'C16 H13 N O5 S'
_chemical_formula_sum            'C16 H13 N O5 S'
_chemical_formula_weight         331.33
_chemical_name_systematic
;
(4-Hydroxy-1,1-dioxo-2H-1,2-benzothiazin-3-yl)(3-methoxyphenyl)methanone
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.5869(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1866(3)
_cell_length_b                   7.2431(3)
_cell_length_c                   25.2452(9)
_cell_measurement_reflns_used    3461
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1489.84(10)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5610
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.378
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0563
_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)+(0.0510P)²+1.1474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                2795
_reflns_number_total             3399
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2296.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225841
_cod_database_fobs_code          2225841
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'
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 0.30794(7) 0.18400(11) 0.10208(2) 0.0519(2) Uani d . 1 . .
O O1 0.1907(2) 0.3174(4) 0.08123(8) 0.0825(8) Uani d . 1 . .
O O2 0.2664(3) -0.0070(3) 0.09981(8) 0.0780(7) Uani d . 1 . .
O O3 0.7829(2) 0.0710(3) 0.18344(8) 0.0532(5) Uani d . 1 . .
H H3O 0.772(4) 0.058(4) 0.2194(12) 0.064 Uiso d . 1 . .
O O4 0.6461(2) 0.0579(3) 0.26917(7) 0.0502(4) Uani d . 1 . .
O O5 0.2363(2) 0.2043(3) 0.40084(7) 0.0639(6) Uani d . 1 . .
N N1 0.3602(2) 0.2363(3) 0.16357(7) 0.0405(4) Uani d . 1 . .
H H1N 0.350(3) 0.347(4) 0.1721(11) 0.049 Uiso d . 1 . .
C C1 0.4921(3) 0.2116(3) 0.07263(9) 0.0443(5) Uani d . 1 . .
C C2 0.4907(4) 0.2573(4) 0.01952(10) 0.0608(7) Uani d . 1 . .
H H2 0.3919 0.2803 -0.0008 0.073 Uiso calc R 1 . .
C C3 0.6372(4) 0.2684(5) -0.00311(11) 0.0669(8) Uani d . 1 . .
H H3 0.6374 0.2979 -0.0390 0.080 Uiso calc R 1 . .
C C4 0.7820(4) 0.2361(5) 0.02714(12) 0.0686(8) Uani d . 1 . .
H H4 0.8802 0.2442 0.0116 0.082 Uiso calc R 1 . .
C C5 0.7853(3) 0.1919(4) 0.08025(11) 0.0561(7) Uani d . 1 . .
H H5 0.8850 0.1703 0.1002 0.067 Uiso calc R 1 . .
C C6 0.6392(3) 0.1796(3) 0.10413(9) 0.0415(5) Uani d . 1 . .
C C7 0.6420(3) 0.1356(3) 0.16109(9) 0.0396(5) Uani d . 1 . .
C C8 0.5064(3) 0.1554(3) 0.18882(8) 0.0382(5) Uani d . 1 . .
C C9 0.5114(3) 0.0999(3) 0.24377(9) 0.0407(5) Uani d . 1 . .
C C10 0.3583(3) 0.0867(3) 0.27107(9) 0.0399(5) Uani d . 1 . .
C C11 0.3629(3) 0.1488(3) 0.32355(9) 0.0433(5) Uani d . 1 . .
H H11 0.4583 0.2005 0.3403 0.052 Uiso calc R 1 . .
C C12 0.2229(3) 0.1324(4) 0.35052(9) 0.0485(6) Uani d . 1 . .
C C13 0.0846(3) 0.0446(4) 0.32655(11) 0.0550(7) Uani d . 1 . .
H H13 -0.0078 0.0308 0.3449 0.066 Uiso calc R 1 . .
C C14 0.0844(3) -0.0224(4) 0.27528(11) 0.0529(6) Uani d . 1 . .
H H14 -0.0076 -0.0845 0.2598 0.063 Uiso calc R 1 . .
C C15 0.2183(3) 0.0011(3) 0.24657(10) 0.0469(5) Uani d . 1 . .
H H15 0.2150 -0.0395 0.2115 0.056 Uiso calc R 1 . .
C C16 0.0876(4) 0.2197(6) 0.42631(13) 0.0785(10) Uani d . 1 . .
H H16A 0.1089 0.2871 0.4590 0.094 Uiso calc R 1 . .
H H16B 0.0480 0.0985 0.4337 0.094 Uiso calc R 1 . .
H H16C 0.0063 0.2837 0.4032 0.094 Uiso calc R 1 . .
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'
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 . . 119.57(16) ?
O2 S1 N1 . . 107.85(12) ?
O1 S1 N1 . . 107.56(13) ?
O2 S1 C1 . . 107.77(12) ?
O1 S1 C1 . . 109.96(13) ?
N1 S1 C1 . . 102.85(11) ?
C7 O3 H3O . . 107.2(19) ?
C12 O5 C16 . . 116.8(2) ?
C8 N1 S1 . . 117.75(15) ?
C8 N1 H1N . . 112.5(19) ?
S1 N1 H1N . . 116.6(19) ?
C2 C1 C6 . . 121.2(2) ?
C2 C1 S1 . . 120.8(2) ?
C6 C1 S1 . . 117.92(17) ?
C1 C2 C3 . . 119.4(3) ?
C1 C2 H2 . . 120.3 ?
C3 C2 H2 . . 120.3 ?
C4 C3 C2 . . 120.0(3) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 121.2(3) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C4 C5 C6 . . 120.0(3) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C5 C6 C1 . . 118.2(2) ?
C5 C6 C7 . . 120.3(2) ?
C1 C6 C7 . . 121.6(2) ?
O3 C7 C8 . . 122.3(2) ?
O3 C7 C6 . . 115.16(19) ?
C8 C7 C6 . . 122.5(2) ?
C7 C8 N1 . . 119.92(19) ?
C7 C8 C9 . . 120.8(2) ?
N1 C8 C9 . . 119.30(19) ?
O4 C9 C8 . . 120.0(2) ?
O4 C9 C10 . . 118.9(2) ?
C8 C9 C10 . . 121.1(2) ?
C15 C10 C11 . . 120.6(2) ?
C15 C10 C9 . . 121.0(2) ?
C11 C10 C9 . . 118.1(2) ?
C12 C11 C10 . . 119.2(2) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
O5 C12 C13 . . 124.7(2) ?
O5 C12 C11 . . 115.2(2) ?
C13 C12 C11 . . 120.1(2) ?
C14 C13 C12 . . 119.8(2) ?
C14 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
C15 C14 C13 . . 121.3(2) ?
C15 C14 H14 . . 119.3 ?
C13 C14 H14 . . 119.3 ?
C14 C15 C10 . . 118.8(2) ?
C14 C15 H15 . . 120.6 ?
C10 C15 H15 . . 120.6 ?
O5 C16 H16A . . 109.5 ?
O5 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O5 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
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 . 1.425(2) ?
S1 O1 . 1.426(2) ?
S1 N1 . 1.6145(19) ?
S1 C1 . 1.756(2) ?
O3 C7 . 1.319(3) ?
O3 H3O . 0.92(3) ?
O4 C9 . 1.257(3) ?
O5 C12 . 1.367(3) ?
O5 C16 . 1.436(3) ?
N1 C8 . 1.426(3) ?
N1 H1N . 0.84(3) ?
C1 C2 . 1.380(3) ?
C1 C6 . 1.396(3) ?
C2 C3 . 1.381(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.366(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.376(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.394(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.471(3) ?
C7 C8 . 1.377(3) ?
C8 C9 . 1.441(3) ?
C9 C10 . 1.491(3) ?
C10 C15 . 1.394(3) ?
C10 C11 . 1.396(3) ?
C11 C12 . 1.394(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.385(4) ?
C13 C14 . 1.382(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.382(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
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
O3 H3O O4 . 0.92(3) 1.70(3) 2.534(2) 148(3)
N1 H1N O4 2_655 0.84(3) 2.13(3) 2.886(3) 151(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_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 C8 . . . . 66.4(2) ?
O1 S1 N1 C8 . . . . -163.37(18) ?
C1 S1 N1 C8 . . . . -47.3(2) ?
O2 S1 C1 C2 . . . . 94.1(3) ?
O1 S1 C1 C2 . . . . -37.8(3) ?
N1 S1 C1 C2 . . . . -152.2(2) ?
O2 S1 C1 C6 . . . . -83.7(2) ?
O1 S1 C1 C6 . . . . 144.4(2) ?
N1 S1 C1 C6 . . . . 30.0(2) ?
C6 C1 C2 C3 . . . . 1.1(4) ?
S1 C1 C2 C3 . . . . -176.6(2) ?
C1 C2 C3 C4 . . . . -0.6(5) ?
C2 C3 C4 C5 . . . . 0.1(5) ?
C3 C4 C5 C6 . . . . -0.1(5) ?
C4 C5 C6 C1 . . . . 0.5(4) ?
C4 C5 C6 C7 . . . . -178.9(3) ?
C2 C1 C6 C5 . . . . -1.1(4) ?
S1 C1 C6 C5 . . . . 176.7(2) ?
C2 C1 C6 C7 . . . . 178.4(2) ?
S1 C1 C6 C7 . . . . -3.8(3) ?
C5 C6 C7 O3 . . . . -14.2(3) ?
C1 C6 C7 O3 . . . . 166.3(2) ?
C5 C6 C7 C8 . . . . 167.5(2) ?
C1 C6 C7 C8 . . . . -11.9(4) ?
O3 C7 C8 N1 . . . . 176.2(2) ?
C6 C7 C8 N1 . . . . -5.7(3) ?
O3 C7 C8 C9 . . . . -2.0(4) ?
C6 C7 C8 C9 . . . . 176.1(2) ?
S1 N1 C8 C7 . . . . 39.2(3) ?
S1 N1 C8 C9 . . . . -142.49(19) ?
C7 C8 C9 O4 . . . . 10.3(4) ?
N1 C8 C9 O4 . . . . -167.9(2) ?
C7 C8 C9 C10 . . . . -168.2(2) ?
N1 C8 C9 C10 . . . . 13.6(3) ?
O4 C9 C10 C15 . . . . -133.0(2) ?
C8 C9 C10 C15 . . . . 45.5(3) ?
O4 C9 C10 C11 . . . . 41.8(3) ?
C8 C9 C10 C11 . . . . -139.7(2) ?
C15 C10 C11 C12 . . . . -3.1(4) ?
C9 C10 C11 C12 . . . . -177.9(2) ?
C16 O5 C12 C13 . . . . -12.1(4) ?
C16 O5 C12 C11 . . . . 169.3(3) ?
C10 C11 C12 O5 . . . . -177.2(2) ?
C10 C11 C12 C13 . . . . 4.2(4) ?
O5 C12 C13 C14 . . . . 179.8(2) ?
C11 C12 C13 C14 . . . . -1.7(4) ?
C12 C13 C14 C15 . . . . -1.9(4) ?
C13 C14 C15 C10 . . . . 3.0(4) ?
C11 C10 C15 C14 . . . . -0.4(4) ?
C9 C10 C15 C14 . . . . 174.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744804
