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#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/18/8101863.cif $
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#
# 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_8101863
loop_
_publ_author_name
'Dupont, L.'
'Boverie, S.'
'Pirotte, B.'
'de Tullio, P.'
_publ_section_title
;
Crystal structure of 7-chloro-3-isopropoxy-4H-1,2,4-benzothiadiazine 
1,1-dioxide monohydrate, C₁₀H₁₁ClN₂O₃S · H₂O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              565
_journal_page_last               566
_journal_volume                  220
_journal_year                    2005
_chemical_formula_moiety         'C10 H11 Cl N2 O3 S , H2 O'
_chemical_formula_structural     'C10H13ClN2O4S &#x00B7; H2O'
_chemical_formula_sum            'C10 H13 Cl N2 O4 S'
_chemical_formula_weight         292.73
_chemical_name_systematic
; 
 7-chloro-3-isopropoxy-4H-1,2,4-benzothiadiazine 1,1-dioxide monohydrate
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens
; 
H atoms were placed at standard calculated positions, except atom H(N4)
and H(water) which were obtained from difference map.
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.921(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.6352(6)
_cell_length_b                   6.8145(7)
_cell_length_c                   12.2805(6)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.3
_cell_measurement_theta_min      37.6
_cell_volume                     1324.58(16)
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Stoe-Siemens AED4'
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1361
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         68.00
_diffrn_reflns_theta_min         3.78
_diffrn_standards_decay_%        6
_diffrn_standards_interval_time  '60 min'
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    4.131
_exptl_absorpt_correction_T_max  0.3704
_exptl_absorpt_correction_T_min  0.2523
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'EMPIR (Stoe & Cie)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0137(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0425
_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)+(0.0890P)²+0.2655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                1043
_reflns_number_total             1298
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1643.cff
_cod_data_source_block           sm0199
_cod_original_sg_symbol_H-M      C12/m1
_cod_database_code               8101863
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
'-x, -y, -z'
'-x, y, -z'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
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 0.35917(4) 0.0000 0.83659(6) 0.0493(3) Uani 1 4 i d S . .
O1 O 0.40575(12) 0.1766(3) 0.83957(16) 0.0806(6) Uani 1 8 j d . . .
N2 N 0.27851(17) 0.0000 0.7259(2) 0.0697(9) Uani 1 4 i d S . .
C3 C 0.20158(18) 0.0000 0.7284(2) 0.0501(7) Uani 1 4 i d S . .
N4 N 0.17674(16) 0.0000 0.8223(2) 0.0454(6) Uani 1 4 i d S . .
H4 H 0.126(3) 0.0000 0.814(3) 0.064(11) Uiso 1 4 i d S . .
C5 C 0.23255(17) 0.0000 0.9329(2) 0.0419(6) Uani 1 4 i d S . .
C6 C 0.20175(19) 0.0000 1.0271(3) 0.0471(7) Uani 1 4 i d S . .
H6 H 0.1438 0.0000 1.0155 0.057 Uiso 1 4 i calc SR . .
C7 C 0.2565(2) 0.0000 1.1356(3) 0.0543(7) Uani 1 4 i d S . .
H7 H 0.2358 0.0000 1.1978 0.065 Uiso 1 4 i calc SR . .
C8 C 0.3437(2) 0.0000 1.1536(3) 0.0542(7) Uani 1 4 i d S . .
C9 C 0.37563(19) 0.0000 1.0634(3) 0.0515(7) Uani 1 4 i d S . .
H9 H 0.4337 0.0000 1.0757 0.062 Uiso 1 4 i calc SR . .
C10 C 0.31961(18) 0.0000 0.9533(2) 0.0434(6) Uani 1 4 i d S . .
O11 O 0.13765(14) 0.0000 0.63331(18) 0.0677(7) Uani 1 4 i d S . .
C12 C 0.1541(2) 0.0000 0.5217(3) 0.0920(16) Uani 1 4 i d S . .
H12 H 0.2150 0.0000 0.5322 0.110 Uiso 1 4 i calc SR . .
C13 C 0.1133(4) 0.1809(7) 0.4603(3) 0.159(2) Uani 1 8 j d . . .
H13A H 0.0552 0.1846 0.4581 0.238 Uiso 1 8 j calc R . .
H13B H 0.1166 0.1797 0.3836 0.238 Uiso 1 8 j calc R . .
H13C H 0.1420 0.2947 0.4998 0.238 Uiso 1 8 j calc R . .
Cl1 Cl 0.41254(7) 0.0000 1.29202(8) 0.0829(4) Uani 1 4 i d S . .
O3 O 0.01236(15) 0.0000 0.8335(3) 0.0764(9) Uani 1 4 i d S . .
H3 H -0.014(2) -0.087(4) 0.832(3) 0.092 Uiso 1 8 j 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
O1 S1 O1 115.14(17) 2 . ?
O1 S1 N2 109.34(10) 2 . ?
O1 S1 N2 109.35(10) . . ?
O1 S1 C10 108.50(9) 2 . ?
O1 S1 C10 108.49(9) . . ?
N2 S1 C10 105.58(14) . . ?
C3 N2 S1 124.2(2) . . ?
N2 C3 O11 121.0(3) . . ?
N2 C3 N4 126.3(3) . . ?
O11 C3 N4 112.7(3) . . ?
C3 N4 C5 123.4(2) . . ?
C3 N4 H4 119(3) . . ?
C5 N4 H4 118(3) . . ?
N4 C5 C10 121.4(2) . . ?
N4 C5 C6 120.2(2) . . ?
C10 C5 C6 118.4(3) . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 Cl1 119.4(3) . . ?
C7 C8 Cl1 119.7(3) . . ?
C8 C9 C10 118.6(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C9 C10 C5 121.7(3) . . ?
C9 C10 S1 119.3(2) . . ?
C5 C10 S1 119.0(2) . . ?
C3 O11 C12 119.6(3) . . ?
O11 C12 C13 106.4(2) . . ?
O11 C12 C13 106.4(2) . 2 ?
C13 C12 C13 111.2(5) . 2 ?
O11 C12 H12 110.9 . . ?
C13 C12 H12 110.9 . . ?
C13 C12 H12 110.9 2 . ?
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 . . ?
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 O1 1.4255(18) 2 ?
S1 O1 1.4255(18) . ?
S1 N2 1.589(3) . ?
S1 C10 1.751(3) . ?
N2 C3 1.289(4) . ?
C3 O11 1.316(4) . ?
C3 N4 1.339(4) . ?
N4 C5 1.389(4) . ?
N4 H4 0.82(4) . ?
C5 C10 1.392(4) . ?
C5 C6 1.402(4) . ?
C6 C7 1.363(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.399(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(4) . ?
C8 Cl1 1.732(3) . ?
C9 C10 1.387(4) . ?
C9 H9 0.9300 . ?
O11 C12 1.479(4) . ?
C12 C13 1.495(5) . ?
C12 C13 1.495(5) 2 ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O3 H3 0.73(3) . ?
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 O3 0.82(4) 1.97(4) 2.780(3) 167(4) .
O3 H3 O1 0.73(3) 2.12(3) 2.844(2) 175(4) 3_445
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
O1 S1 N2 C3 116.55(9) 2 . . . ?
O1 S1 N2 C3 -116.55(9) . . . . ?
C10 S1 N2 C3 0.0 . . . . ?
S1 N2 C3 O11 180.0 . . . . ?
S1 N2 C3 N4 0.000 . . . . ?
N2 C3 N4 C5 0.000 . . . . ?
O11 C3 N4 C5 180.0 . . . . ?
C3 N4 C5 C10 0.000 . . . . ?
C3 N4 C5 C6 180.000 . . . . ?
N4 C5 C6 C7 180.000 . . . . ?
C10 C5 C6 C7 0.000 . . . . ?
C5 C6 C7 C8 0.000 . . . . ?
C6 C7 C8 C9 0.000 . . . . ?
C6 C7 C8 Cl1 180.000 . . . . ?
C7 C8 C9 C10 0.000 . . . . ?
Cl1 C8 C9 C10 180.000 . . . . ?
C8 C9 C10 C5 0.000 . . . . ?
C8 C9 C10 S1 180.000 . . . . ?
N4 C5 C10 C9 180.000 . . . . ?
C6 C5 C10 C9 0.000 . . . . ?
N4 C5 C10 S1 0.000 . . . . ?
C6 C5 C10 S1 180.0 . . . . ?
O1 S1 C10 C9 62.88(10) 2 . . . ?
O1 S1 C10 C9 -62.88(10) . . . . ?
N2 S1 C10 C9 180.0 . . . . ?
O1 S1 C10 C5 -117.12(10) 2 . . . ?
O1 S1 C10 C5 117.12(10) . . . . ?
N2 S1 C10 C5 0.000 . . . . ?
N2 C3 O11 C12 0.000 . . . . ?
N4 C3 O11 C12 180.0 . . . . ?
C3 O11 C12 C13 -120.7(3) . . . . ?
C3 O11 C12 C13 120.7(3) . . . 2 ?
