#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224319.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_2224319
loop_
_publ_author_name
'Arshad, Muhammad Nadeem'
'Zia-ur-Rehman, Muhammad'
'Khan, Islam Ullah'
_publ_section_title
;
 Methyl 4-hydroxy-2-propyl-2H-1,2-benzothiazine-3-carboxylate
 1,1-dioxide
;
_journal_coeditor_code           IS2482
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3025
_journal_paper_doi               10.1107/S1600536809046236
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H15 N O5 S'
_chemical_formula_moiety         'C13 H15 N O5 S'
_chemical_formula_sum            'C13 H15 N O5 S'
_chemical_formula_weight         297.32
_chemical_name_systematic
;Methyl 4-hydroxy-2-propyl-2H-1,2-benzothiazine-3-carboxylate
 1,1-dioxide
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4398(6)
_cell_length_b                   8.7538(5)
_cell_length_c                   12.7288(7)
_cell_measurement_reflns_used    2980
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.33
_cell_volume                     1386.11(13)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and Mercury (Macrae et al.,  2006)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8843
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.9728
_exptl_absorpt_correction_T_min  0.9081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rods
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.224
_refine_ls_abs_structure_details 'Flack (1983), 1451 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3252
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0360
_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)+(0.0496P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                2540
_reflns_number_total             3252
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2482.cif
_cod_data_source_block           I
_cod_database_code               2224319
_cod_database_fobs_code          2224319
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
C C1 0.58950(17) 0.7963(3) 0.8319(2) 0.0442(5) Uani d . 1 . .
C C2 0.66903(18) 0.8114(3) 0.7577(2) 0.0565(6) Uani d . 1 . .
H H2 0.7391 0.7816 0.7726 0.068 Uiso calc R 1 . .
C C3 0.6434(2) 0.8714(3) 0.6609(3) 0.0703(8) Uani d . 1 . .
H H3 0.6967 0.8829 0.6103 0.084 Uiso calc R 1 . .
C C4 0.5396(2) 0.9145(3) 0.6385(2) 0.0622(7) Uani d . 1 . .
H H4 0.5230 0.9536 0.5725 0.075 Uiso calc R 1 . .
C C5 0.45981(19) 0.9001(3) 0.71319(19) 0.0509(6) Uani d . 1 . .
H H5 0.3900 0.9308 0.6976 0.061 Uiso calc R 1 . .
C C6 0.48305(15) 0.8403(3) 0.81103(17) 0.0407(5) Uani d . 1 . .
C C7 0.39979(15) 0.8187(3) 0.89165(18) 0.0398(5) Uani d . 1 . .
C C8 0.40966(15) 0.7206(2) 0.97246(19) 0.0389(5) Uani d . 1 . .
C C9 0.32273(17) 0.7043(3) 1.04807(18) 0.0443(5) Uani d . 1 . .
C C10 0.2568(3) 0.5866(3) 1.2006(3) 0.0755(8) Uani d . 1 . .
H H10A 0.1955 0.5455 1.1645 0.113 Uiso calc R 1 . .
H H10B 0.2378 0.6825 1.2322 0.113 Uiso calc R 1 . .
H H10C 0.2794 0.5165 1.2542 0.113 Uiso calc R 1 . .
C C11 0.50112(17) 0.4660(3) 0.9658(2) 0.0493(5) Uani d . 1 . .
H H11A 0.4465 0.4214 1.0107 0.059 Uiso calc R 1 . .
H H11B 0.5695 0.4204 0.9848 0.059 Uiso calc R 1 . .
C C12 0.4761(2) 0.4257(3) 0.8530(2) 0.0589(7) Uani d . 1 . .
H H12A 0.5279 0.4748 0.8072 0.071 Uiso calc R 1 . .
H H12B 0.4052 0.4639 0.8350 0.071 Uiso calc R 1 . .
C C13 0.4794(3) 0.2548(3) 0.8355(3) 0.0812(10) Uani d . 1 . .
H H13A 0.4297 0.2057 0.8823 0.122 Uiso calc R 1 . .
H H13B 0.5507 0.2178 0.8490 0.122 Uiso calc R 1 . .
H H13C 0.4600 0.2325 0.7641 0.122 Uiso calc R 1 . .
N N1 0.50637(13) 0.6325(2) 0.98684(13) 0.0423(5) Uani d . 1 . .
O O1 0.70303(11) 0.6188(2) 0.95391(16) 0.0633(5) Uani d . 1 . .
O O2 0.62415(13) 0.8534(2) 1.02728(17) 0.0676(6) Uani d . 1 . .
O O3 0.31275(12) 0.90699(18) 0.87688(13) 0.0532(4) Uani d . 1 . .
H H3A 0.2671 0.8861 0.9211 0.080 Uiso calc R 1 . .
O O4 0.23788(13) 0.7728(2) 1.03972(15) 0.0586(5) Uani d . 1 . .
O O5 0.34308(13) 0.60963(19) 1.12699(13) 0.0547(4) Uani d . 1 . .
S S1 0.61649(4) 0.72551(7) 0.95848(6) 0.04848(16) Uani d . 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
C2 C1 C6 . . 121.5(2) ?
C2 C1 S1 . . 121.76(19) ?
C6 C1 S1 . . 116.72(17) ?
C1 C2 C3 . . 119.0(2) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C4 C3 C2 . . 120.5(2) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 120.5(3) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.4(2) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 C1 . . 118.1(2) ?
C5 C6 C7 . . 122.04(19) ?
C1 C6 C7 . . 119.8(2) ?
O3 C7 C8 . . 123.2(2) ?
O3 C7 C6 . . 113.3(2) ?
C8 C7 C6 . . 123.46(18) ?
C7 C8 N1 . . 120.99(19) ?
C7 C8 C9 . . 120.03(18) ?
N1 C8 C9 . . 118.98(19) ?
O4 C9 O5 . . 122.6(2) ?
O4 C9 C8 . . 122.6(2) ?
O5 C9 C8 . . 114.85(18) ?
O5 C10 H10A . . 109.5 ?
O5 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
O5 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N1 C11 C12 . . 114.2(2) ?
N1 C11 H11A . . 108.7 ?
C12 C11 H11A . . 108.7 ?
N1 C11 H11B . . 108.7 ?
C12 C11 H11B . . 108.7 ?
H11A C11 H11B . . 107.6 ?
C11 C12 C13 . . 111.4(2) ?
C11 C12 H12A . . 109.3 ?
C13 C12 H12A . . 109.3 ?
C11 C12 H12B . . 109.3 ?
C13 C12 H12B . . 109.3 ?
H12A C12 H12B . . 108.0 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C8 N1 C11 . . 117.79(16) ?
C8 N1 S1 . . 113.92(15) ?
C11 N1 S1 . . 119.13(14) ?
C7 O3 H3A . . 109.5 ?
C9 O5 C10 . . 115.99(19) ?
O2 S1 O1 . . 119.30(11) ?
O2 S1 N1 . . 108.17(11) ?
O1 S1 N1 . . 108.37(10) ?
O2 S1 C1 . . 107.40(13) ?
O1 S1 C1 . . 109.72(11) ?
N1 S1 C1 . . 102.59(9) ?
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
C1 C2 . 1.374(3) ?
C1 C6 . 1.404(3) ?
C1 S1 . 1.759(3) ?
C2 C3 . 1.376(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.375(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.380(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.382(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.470(3) ?
C7 O3 . 1.344(2) ?
C7 C8 . 1.346(3) ?
C8 N1 . 1.441(3) ?
C8 C9 . 1.455(3) ?
C9 O4 . 1.219(3) ?
C9 O5 . 1.327(3) ?
C10 O5 . 1.439(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 N1 . 1.483(3) ?
C11 C12 . 1.511(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.513(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
N1 S1 . 1.6339(19) ?
O1 S1 . 1.4268(15) ?
O2 S1 . 1.425(2) ?
O3 H3A . 0.8200 ?
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 H3A O4 . 0.82 1.84 2.558(2) 145
C3 H3 O2 4_654 0.93 2.48 3.358(3) 158
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
C6 C1 C2 C3 . . . . 0.1(4) ?
S1 C1 C2 C3 . . . . -178.3(2) ?
C1 C2 C3 C4 . . . . -0.5(4) ?
C2 C3 C4 C5 . . . . 0.9(4) ?
C3 C4 C5 C6 . . . . -0.9(4) ?
C4 C5 C6 C1 . . . . 0.5(3) ?
C4 C5 C6 C7 . . . . -178.1(2) ?
C2 C1 C6 C5 . . . . -0.1(3) ?
S1 C1 C6 C5 . . . . 178.34(18) ?
C2 C1 C6 C7 . . . . 178.5(2) ?
S1 C1 C6 C7 . . . . -3.0(3) ?
C5 C6 C7 O3 . . . . -21.8(3) ?
C1 C6 C7 O3 . . . . 159.7(2) ?
C5 C6 C7 C8 . . . . 158.4(2) ?
C1 C6 C7 C8 . . . . -20.2(3) ?
O3 C7 C8 N1 . . . . -177.71(19) ?
C6 C7 C8 N1 . . . . 2.1(3) ?
O3 C7 C8 C9 . . . . 1.1(3) ?
C6 C7 C8 C9 . . . . -179.1(2) ?
C7 C8 C9 O4 . . . . 2.6(3) ?
N1 C8 C9 O4 . . . . -178.5(2) ?
C7 C8 C9 O5 . . . . -177.1(2) ?
N1 C8 C9 O5 . . . . 1.8(3) ?
N1 C11 C12 C13 . . . . 176.1(2) ?
C7 C8 N1 C11 . . . . -108.9(2) ?
C9 C8 N1 C11 . . . . 72.3(3) ?
C7 C8 N1 S1 . . . . 37.8(3) ?
C9 C8 N1 S1 . . . . -141.04(17) ?
C12 C11 N1 C8 . . . . 63.6(3) ?
C12 C11 N1 S1 . . . . -81.3(2) ?
O4 C9 O5 C10 . . . . 2.7(3) ?
C8 C9 O5 C10 . . . . -177.5(2) ?
C8 N1 S1 O2 . . . . 61.60(18) ?
C11 N1 S1 O2 . . . . -152.19(18) ?
C8 N1 S1 O1 . . . . -167.73(15) ?
C11 N1 S1 O1 . . . . -21.5(2) ?
C8 N1 S1 C1 . . . . -51.72(16) ?
C11 N1 S1 C1 . . . . 94.49(18) ?
C2 C1 S1 O2 . . . . 100.0(2) ?
C6 C1 S1 O2 . . . . -78.46(19) ?
C2 C1 S1 O1 . . . . -31.1(2) ?
C6 C1 S1 O1 . . . . 150.46(17) ?
C2 C1 S1 N1 . . . . -146.1(2) ?
C6 C1 S1 N1 . . . . 35.43(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14969696
