#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/87/2228782.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_2228782
loop_
_publ_author_name
'Bassin, Jatinder P.'
'Shah, Virender P.'
'Martin, Lee'
'Clegg, William'
'Harrington, Ross W.'
_publ_section_title
;
 (Z)-3-Chloromethylidene-5,6-dimethoxy-2-methyl-2,3-dihydro-1,2-benzothiazole
 1,1-dioxide
;
_journal_coeditor_code           JH2234
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o12
_journal_paper_doi               10.1107/S1600536810049561
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H12 Cl N O4 S'
_chemical_formula_moiety         'C11 H12 Cl N O4 S'
_chemical_formula_sum            'C11 H12 Cl N O4 S'
_chemical_formula_weight         289.73
_chemical_name_systematic
;
(Z)-3-Chloromethylidene-5,6-dimethoxy-2-methyl-2,3-
dihydro-1,2-benzothiazole 1,1-dioxide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.875(11)
_cell_angle_beta                 86.293(10)
_cell_angle_gamma                84.176(11)
_cell_formula_units_Z            2
_cell_length_a                   7.578(5)
_cell_length_b                   7.904(6)
_cell_length_c                   10.002(7)
_cell_measurement_reflns_used    974
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.46
_cell_measurement_theta_min      2.64
_cell_volume                     594.7(7)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'thin-slice ω'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6937
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.1080
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4651
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.289
_refine_diff_density_min         -0.434
_refine_ls_extinction_coef       0.084(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0652
_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)+(0.0319P)²+1.6618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1766
_reflns_number_gt                1671
_reflns_number_total             2237
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2234.cif
_cod_data_source_block           I
_cod_database_code               2228782
_cod_database_fobs_code          2228782
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.20714(16) 0.29186(15) 0.38990(10) 0.0286(4) Uani d . 1 . .
Cl Cl1 0.72928(18) 0.01424(17) 0.14119(11) 0.0402(4) Uani d . 1 . .
N N1 0.3721(5) 0.2029(5) 0.2891(3) 0.0315(9) Uani d . 1 . .
C C1 0.3515(8) 0.2190(8) 0.1449(4) 0.0441(14) Uani d . 1 . .
H H1A 0.4303 0.3002 0.1058 0.066 Uiso calc R 1 . .
H H1B 0.2279 0.2595 0.1290 0.066 Uiso calc R 1 . .
H H1C 0.3823 0.1079 0.1031 0.066 Uiso calc R 1 . .
C C2 0.5330(6) 0.1725(6) 0.3483(4) 0.0277(10) Uani d . 1 . .
C C3 0.6901(7) 0.0988(6) 0.2982(4) 0.0353(12) Uani d . 1 . .
H H3 0.7873 0.0931 0.3541 0.042 Uiso calc R 1 . .
C C4 0.5098(6) 0.2358(5) 0.4871(4) 0.0255(10) Uani d . 1 . .
C C5 0.6343(6) 0.2194(6) 0.5848(4) 0.0270(10) Uani d . 1 . .
H H5 0.7509 0.1660 0.5653 0.032 Uiso calc R 1 . .
C C6 0.5834(6) 0.2829(6) 0.7102(4) 0.0268(10) Uani d . 1 . .
C C7 0.4134(6) 0.3697(6) 0.7387(4) 0.0255(10) Uani d . 1 . .
C C8 0.2894(6) 0.3844(6) 0.6435(4) 0.0271(10) Uani d . 1 . .
H H8 0.1733 0.4400 0.6615 0.033 Uiso calc R 1 . .
C C9 0.3435(6) 0.3132(6) 0.5189(4) 0.0250(10) Uani d . 1 . .
C C10 0.8610(6) 0.1808(6) 0.7939(5) 0.0328(11) Uani d . 1 . .
H H10A 0.8510 0.0663 0.7612 0.049 Uiso calc R 1 . .
H H10B 0.9205 0.1726 0.8782 0.049 Uiso calc R 1 . .
H H10C 0.9306 0.2431 0.7271 0.049 Uiso calc R 1 . .
C C11 0.2152(7) 0.5175(7) 0.8980(5) 0.0354(11) Uani d . 1 . .
H H11A 0.1882 0.6091 0.8329 0.053 Uiso calc R 1 . .
H H11B 0.2138 0.5654 0.9878 0.053 Uiso calc R 1 . .
H H11C 0.1258 0.4362 0.8971 0.053 Uiso calc R 1 . .
O O1 0.0829(5) 0.1725(4) 0.4255(3) 0.0371(8) Uani d . 1 . .
O O2 0.1341(5) 0.4480(4) 0.3321(3) 0.0358(8) Uani d . 1 . .
O O3 0.6882(4) 0.2685(4) 0.8156(3) 0.0316(8) Uani d . 1 . .
O O4 0.3860(4) 0.4328(4) 0.8638(3) 0.0320(8) 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'
Cl Cl 0.1484 0.1585 '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
N1 S1 C9 . . 93.3(2) ?
N1 S1 O1 . . 110.3(2) ?
N1 S1 O2 . . 109.9(2) ?
C9 S1 O1 . . 110.6(2) ?
C9 S1 O2 . . 115.1(2) ?
O1 S1 O2 . . 115.4(2) ?
S1 N1 C1 . . 117.1(3) ?
S1 N1 C2 . . 114.2(3) ?
C1 N1 C2 . . 125.1(4) ?
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1B . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 C3 . . 129.9(4) ?
N1 C2 C4 . . 108.7(4) ?
C3 C2 C4 . . 121.4(4) ?
Cl1 C3 C2 . . 125.2(4) ?
Cl1 C3 H3 . . 117.4 ?
C2 C3 H3 . . 117.4 ?
C2 C4 C5 . . 127.5(4) ?
C2 C4 C9 . . 113.3(4) ?
C5 C4 C9 . . 119.3(4) ?
C4 C5 H5 . . 120.9 ?
C4 C5 C6 . . 118.2(4) ?
H5 C5 C6 . . 120.9 ?
C5 C6 C7 . . 121.5(4) ?
C5 C6 O3 . . 124.1(4) ?
C7 C6 O3 . . 114.4(4) ?
C6 C7 C8 . . 120.6(4) ?
C6 C7 O4 . . 114.7(4) ?
C8 C7 O4 . . 124.7(4) ?
C7 C8 H8 . . 121.8 ?
C7 C8 C9 . . 116.3(4) ?
H8 C8 C9 . . 121.8 ?
S1 C9 C4 . . 110.2(3) ?
S1 C9 C8 . . 125.5(4) ?
C4 C9 C8 . . 124.1(4) ?
H10A C10 H10B . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10A C10 O3 . . 109.5 ?
H10B C10 H10C . . 109.5 ?
H10B C10 O3 . . 109.5 ?
H10C C10 O3 . . 109.5 ?
H11A C11 H11B . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11A C11 O4 . . 109.5 ?
H11B C11 H11C . . 109.5 ?
H11B C11 O4 . . 109.5 ?
H11C C11 O4 . . 109.5 ?
C6 O3 C10 . . 117.2(4) ?
C7 O4 C11 . . 116.7(4) ?
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 N1 . 1.661(4) ?
S1 C9 . 1.725(4) ?
S1 O1 . 1.424(4) ?
S1 O2 . 1.427(3) ?
Cl1 C3 . 1.715(5) ?
N1 C1 . 1.463(5) ?
N1 C2 . 1.387(6) ?
C1 H1A . 0.980 ?
C1 H1B . 0.980 ?
C1 H1C . 0.980 ?
C2 C3 . 1.342(7) ?
C2 C4 . 1.478(6) ?
C3 H3 . 0.950 ?
C4 C5 . 1.397(6) ?
C4 C9 . 1.365(6) ?
C5 H5 . 0.950 ?
C5 C6 . 1.377(6) ?
C6 C7 . 1.411(7) ?
C6 O3 . 1.357(5) ?
C7 C8 . 1.376(6) ?
C7 O4 . 1.352(5) ?
C8 H8 . 0.950 ?
C8 C9 . 1.398(6) ?
C10 H10A . 0.980 ?
C10 H10B . 0.980 ?
C10 H10C . 0.980 ?
C10 O3 . 1.424(6) ?
C11 H11A . 0.980 ?
C11 H11B . 0.980 ?
C11 H11C . 0.980 ?
C11 O4 . 1.420(6) ?
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
C9 S1 N1 C1 . . . . -155.2(4) ?
C9 S1 N1 C2 . . . . 4.6(4) ?
O1 S1 N1 C1 . . . . 91.4(4) ?
O1 S1 N1 C2 . . . . -108.8(3) ?
O2 S1 N1 C1 . . . . -37.0(4) ?
O2 S1 N1 C2 . . . . 122.8(3) ?
S1 N1 C2 C3 . . . . 177.8(4) ?
S1 N1 C2 C4 . . . . -1.8(5) ?
C1 N1 C2 C3 . . . . -24.3(8) ?
C1 N1 C2 C4 . . . . 156.1(5) ?
N1 C2 C3 Cl1 . . . . -2.1(7) ?
C4 C2 C3 Cl1 . . . . 177.5(3) ?
N1 C2 C4 C5 . . . . 174.9(4) ?
N1 C2 C4 C9 . . . . -2.9(5) ?
C3 C2 C4 C5 . . . . -4.8(7) ?
C3 C2 C4 C9 . . . . 177.4(4) ?
C2 C4 C5 C6 . . . . -177.8(4) ?
C9 C4 C5 C6 . . . . 0.0(6) ?
C4 C5 C6 C7 . . . . -3.1(7) ?
C4 C5 C6 O3 . . . . 176.8(4) ?
C5 C6 C7 C8 . . . . 3.9(7) ?
C5 C6 C7 O4 . . . . -176.5(4) ?
O3 C6 C7 C8 . . . . -176.0(4) ?
O3 C6 C7 O4 . . . . 3.6(6) ?
C6 C7 C8 C9 . . . . -1.5(6) ?
O4 C7 C8 C9 . . . . 178.9(4) ?
C2 C4 C9 S1 . . . . 6.2(5) ?
C2 C4 C9 C8 . . . . -179.5(4) ?
C5 C4 C9 S1 . . . . -171.9(3) ?
C5 C4 C9 C8 . . . . 2.5(7) ?
C7 C8 C9 S1 . . . . 171.8(3) ?
C7 C8 C9 C4 . . . . -1.6(7) ?
N1 S1 C9 C4 . . . . -6.2(3) ?
N1 S1 C9 C8 . . . . 179.6(4) ?
O1 S1 C9 C4 . . . . 107.0(3) ?
O1 S1 C9 C8 . . . . -67.3(4) ?
O2 S1 C9 C4 . . . . -120.0(3) ?
O2 S1 C9 C8 . . . . 65.8(4) ?
C5 C6 O3 C10 . . . . -0.5(6) ?
C7 C6 O3 C10 . . . . 179.4(4) ?
C6 C7 O4 C11 . . . . -178.5(4) ?
C8 C7 O4 C11 . . . . 1.1(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656425
