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#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/18/8101828.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8101828
loop_
_publ_author_name
'L. Dupont'
'S. Boverie'
'P. de Tullio'
'B. Pirotte'
_publ_section_title
;
Crystal structure of 7-chloro-3-isopropylsulfanyl-4H-1,2,4-benzothiadiazine 
1,1-dioxide, C₁₀H₁₁ClN₂O₂S₂
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              467
_journal_page_last               468
_journal_volume                  220
_journal_year                    2005
_chemical_formula_moiety         'C10 H11 Cl N2 O2 S2'
_chemical_formula_sum            'C10 H11 Cl N2 O2 S2'
_chemical_formula_weight         290.78
_chemical_name_systematic
; 
 7-Chloro-3-isopropylsulfanyl-4H-1,2,4-benzothiadiazine 1,1-dioxide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_space_group_name_H-M   'P c a b'
_atom_sites_solution_hydrogens
;   
H atoms were placed at standard calculated positions, except atom H(N4)
which was obtained from difference map.
;
_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            8
_cell_length_a                   8.5908(5)
_cell_length_b                   12.0056(8)
_cell_length_c                   24.2133(13)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.4
_cell_measurement_theta_min      37.5
_cell_volume                     2497.3(3)
_computing_cell_refinement       'DIF4 (Stoe & Cie)'
_computing_data_collection       'DIF4 (Stoe & Cie)'
_computing_data_reduction        'REDU4 (Stoe & Cie)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Stoe-Siemens AED'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2242
_diffrn_reflns_theta_full        68.05
_diffrn_reflns_theta_max         68.05
_diffrn_reflns_theta_min         3.65
_diffrn_standards_decay_%        6
_diffrn_standards_interval_time  '60 min'
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    5.779
_exptl_absorpt_correction_T_max  0.530
_exptl_absorpt_correction_T_min  0.109
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'EMPIR (Stoe & Cie)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.0044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0576
_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)+(0.1300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1691
_reflns_number_gt                1463
_reflns_number_total             2242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1595.cff
_cod_data_source_block           sm0198
_cod_original_sg_symbol_H-M      Pcab
_cod_database_code               8101828
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x-1/2, -y-1/2, z'
'-x-1/2, y, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.17891(11) 0.02418(7) 0.40516(4) 0.0446(3) Uani 1 8 c d . . .
O1 O 0.0215(3) 0.0626(2) 0.41095(12) 0.0561(7) Uani 1 8 c d . . .
O2 O 0.1991(4) -0.0932(2) 0.40058(11) 0.0581(8) Uani 1 8 c d . . .
N2 N 0.2550(4) 0.0843(3) 0.35248(12) 0.0516(8) Uani 1 8 c d . . .
C3 C 0.3292(5) 0.1792(3) 0.35687(15) 0.0485(9) Uani 1 8 c d . . .
N4 N 0.3669(4) 0.2299(3) 0.40531(13) 0.0530(9) Uani 1 8 c d . . .
H4 H 0.416(5) 0.292(4) 0.4047(18) 0.064 Uiso 1 8 c d . . .
C5 C 0.3591(4) 0.1760(3) 0.45674(15) 0.0470(9) Uani 1 8 c d . . .
C6 C 0.4335(6) 0.2214(3) 0.50238(16) 0.0558(10) Uani 1 8 c d . . .
H6 H 0.4850 0.2892 0.4993 0.067 Uiso 1 8 c calc R . .
C7 C 0.4310(5) 0.1652(4) 0.55278(16) 0.0589(11) Uani 1 8 c d . . .
H7 H 0.4789 0.1962 0.5836 0.071 Uiso 1 8 c calc R . .
C8 C 0.3569(5) 0.0633(4) 0.55660(15) 0.0490(9) Uani 1 8 c d . . .
C9 C 0.2831(5) 0.0172(3) 0.51225(15) 0.0508(10) Uani 1 8 c d . . .
H9 H 0.2331 -0.0512 0.5154 0.061 Uiso 1 8 c calc R . .
C10 C 0.2837(4) 0.0749(3) 0.46151(14) 0.0458(8) Uani 1 8 c d . . .
S11 S 0.39483(15) 0.25171(10) 0.29941(4) 0.0621(4) Uani 1 8 c d . . .
C12 C 0.3489(5) 0.1591(4) 0.24228(16) 0.0580(11) Uani 1 8 c d . . .
H12 H 0.2404 0.1347 0.2453 0.070 Uiso 1 8 c calc R . .
C13 C 0.4528(8) 0.0598(4) 0.2406(2) 0.0831(16) Uani 1 8 c d . . .
H13A H 0.4289 0.0158 0.2086 0.125 Uiso 1 8 c calc R . .
H13B H 0.4372 0.0159 0.2733 0.125 Uiso 1 8 c calc R . .
H13C H 0.5594 0.0837 0.2389 0.125 Uiso 1 8 c calc R . .
C14 C 0.3678(7) 0.2317(4) 0.19064(17) 0.0758(15) Uani 1 8 c d . . .
H14A H 0.4728 0.2585 0.1885 0.114 Uiso 1 8 c calc R . .
H14B H 0.2975 0.2937 0.1926 0.114 Uiso 1 8 c calc R . .
H14C H 0.3447 0.1882 0.1584 0.114 Uiso 1 8 c calc R . .
Cl1 Cl 0.35899(15) -0.00688(10) 0.61909(4) 0.0669(4) Uani 1 8 c d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 116.12(18) . . ?
O2 S1 N2 109.47(17) . . ?
O1 S1 N2 108.48(18) . . ?
O2 S1 C10 110.08(18) . . ?
O1 S1 C10 107.33(18) . . ?
N2 S1 C10 104.75(17) . . ?
C3 N2 S1 121.6(3) . . ?
N2 C3 N4 125.1(4) . . ?
N2 C3 S11 122.0(3) . . ?
N4 C3 S11 112.9(3) . . ?
C3 N4 C5 123.1(3) . . ?
C3 N4 H4 120(3) . . ?
C5 N4 H4 116(3) . . ?
C6 C5 C10 119.6(3) . . ?
C6 C5 N4 120.2(4) . . ?
C10 C5 N4 120.1(3) . . ?
C5 C6 C7 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.6(4) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 121.4(4) . . ?
C9 C8 Cl1 119.6(3) . . ?
C7 C8 Cl1 119.0(3) . . ?
C8 C9 C10 119.0(4) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C5 C10 C9 120.4(3) . . ?
C5 C10 S1 118.9(3) . . ?
C9 C10 S1 120.5(3) . . ?
C3 S11 C12 103.46(19) . . ?
C13 C12 C14 111.7(4) . . ?
C13 C12 S11 112.3(3) . . ?
C14 C12 S11 104.5(3) . . ?
C13 C12 H12 109.4 . . ?
C14 C12 H12 109.4 . . ?
S11 C12 H12 109.4 . . ?
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 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.424(3) . ?
S1 O1 1.436(3) . ?
S1 N2 1.605(3) . ?
S1 C10 1.744(4) . ?
N2 C3 1.310(5) . ?
C3 N4 1.360(5) . ?
C3 S11 1.736(4) . ?
N4 C5 1.405(4) . ?
N4 H4 0.85(5) . ?
C5 C6 1.388(5) . ?
C5 C10 1.381(5) . ?
C6 C7 1.394(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.365(5) . ?
C8 Cl1 1.732(4) . ?
C9 C10 1.410(5) . ?
C9 H9 0.9300 . ?
S11 C12 1.818(4) . ?
C12 C13 1.490(7) . ?
C12 C14 1.532(5) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 O1 0.85(5) 1.98(5) 2.826(4) 174(4) 7_665
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N2 C3 -142.1(3) . . . . ?
O1 S1 N2 C3 90.3(4) . . . . ?
C10 S1 N2 C3 -24.1(4) . . . . ?
S1 N2 C3 N4 8.5(6) . . . . ?
S1 N2 C3 S11 -173.4(2) . . . . ?
N2 C3 N4 C5 13.4(7) . . . . ?
S11 C3 N4 C5 -164.8(3) . . . . ?
C3 N4 C5 C6 164.3(4) . . . . ?
C3 N4 C5 C10 -12.5(6) . . . . ?
C10 C5 C6 C7 -0.4(6) . . . . ?
N4 C5 C6 C7 -177.3(4) . . . . ?
C5 C6 C7 C8 1.4(7) . . . . ?
C6 C7 C8 C9 -1.4(7) . . . . ?
C6 C7 C8 Cl1 178.5(3) . . . . ?
C7 C8 C9 C10 0.4(6) . . . . ?
Cl1 C8 C9 C10 -179.4(3) . . . . ?
C6 C5 C10 C9 -0.5(6) . . . . ?
N4 C5 C10 C9 176.3(4) . . . . ?
C6 C5 C10 S1 175.3(3) . . . . ?
N4 C5 C10 S1 -7.8(5) . . . . ?
C8 C9 C10 C5 0.5(6) . . . . ?
C8 C9 C10 S1 -175.3(3) . . . . ?
O2 S1 C10 C5 141.2(3) . . . . ?
O1 S1 C10 C5 -91.6(3) . . . . ?
N2 S1 C10 C5 23.6(3) . . . . ?
O2 S1 C10 C9 -43.0(4) . . . . ?
O1 S1 C10 C9 84.3(3) . . . . ?
N2 S1 C10 C9 -160.6(3) . . . . ?
N2 C3 S11 C12 -4.5(4) . . . . ?
N4 C3 S11 C12 173.8(3) . . . . ?
C3 S11 C12 C13 -72.3(4) . . . . ?
C3 S11 C12 C14 166.5(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25848999
