#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/54/2225490.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_2225490
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Shakuntala, K.'
'Fuess, Hartmut'
_publ_section_title
;
 Sodium N,2-dichlorobenzenesulfonamidate sesquihydrate
;
_journal_coeditor_code           BX2268
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o889
_journal_paper_doi               10.1107/S1600536810009864
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'Na +, C6 H4 Cl2 N O2 S -, 1.5H2 O'
_chemical_formula_moiety         'Na +, C6 H4 Cl2 N O2 S -, 1.5(H2 O)'
_chemical_formula_sum            'C6 H7 Cl2 N Na O3.5 S'
_chemical_formula_weight         275.08
_chemical_name_systematic
;
Sodium N,2-dichlorobenzenesulfonamidate sesquihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 102.274(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.1288(7)
_cell_length_b                   6.6724(4)
_cell_length_c                   28.144(2)
_cell_measurement_reflns_used    2816
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.96
_cell_volume                     2042.1(2)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega and phi scans
;
_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  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0116
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            6590
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.96
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.7935
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2076
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0246P)²+3.4504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0687
_reflns_number_gt                1944
_reflns_number_total             2076
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bx2268.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C6 H7 Cl2 N1 Na1 O3.5 S1'
_cod_database_code               2225490
_cod_database_fobs_code          2225490
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C C1 0.31355(16) 0.8280(3) 0.10792(6) 0.0208(4) Uani d . 1 . .
C C2 0.39097(18) 0.8966(3) 0.07759(7) 0.0257(4) Uani d . 1 . .
C C3 0.3434(2) 0.9809(3) 0.03289(8) 0.0376(5) Uani d . 1 . .
H H3 0.3951 1.0261 0.0132 0.045 Uiso calc R 1 . .
C C4 0.2181(2) 0.9965(4) 0.01810(8) 0.0454(6) Uani d . 1 . .
H H4 0.1843 1.0514 -0.0122 0.054 Uiso calc R 1 . .
C C5 0.1413(2) 0.9312(4) 0.04792(9) 0.0431(6) Uani d . 1 . .
H H5 0.0566 0.9446 0.0375 0.052 Uiso calc R 1 . .
C C6 0.18813(18) 0.8472(3) 0.09260(7) 0.0301(4) Uani d . 1 . .
H H6 0.1358 0.8038 0.1122 0.036 Uiso calc R 1 . .
Cl Cl1 0.38325(5) 0.35684(8) 0.123234(19) 0.03468(14) Uani d . 1 . .
Cl Cl2 0.54842(5) 0.88282(9) 0.09392(2) 0.04180(16) Uani d . 1 . .
N N1 0.45784(14) 0.5415(2) 0.16212(6) 0.0255(3) Uani d . 1 . .
Na Na1 0.14395(7) 0.50352(13) 0.23560(3) 0.03065(19) Uani d . 1 . .
O O1 0.25555(13) 0.6627(2) 0.18286(5) 0.0329(3) Uani d . 1 . .
O O2 0.44039(12) 0.8680(2) 0.19636(5) 0.0295(3) Uani d . 1 . .
O O3 0.29191(13) 0.6793(2) 0.29703(5) 0.0333(3) Uani d D 1 . .
H H31 0.3538(18) 0.627(4) 0.3106(9) 0.040 Uiso d D 1 . .
H H32 0.258(2) 0.718(4) 0.3182(8) 0.040 Uiso d D 1 . .
O O4 0.0000 0.7742(3) 0.2500 0.0336(5) Uani d SD 1 . .
H H41 0.013(2) 0.852(3) 0.2729(7) 0.040 Uiso d D 1 . .
S S1 0.36626(4) 0.71995(7) 0.166416(15) 0.02023(12) 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'
Cl Cl 0.1484 0.1585 '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'
Na Na 0.0362 0.0249 '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
C6 C1 C2 . . 119.28(17) ?
C6 C1 S1 . . 116.14(14) ?
C2 C1 S1 . . 124.58(14) ?
C3 C2 C1 . . 121.30(19) ?
C3 C2 Cl2 . . 116.02(16) ?
C1 C2 Cl2 . . 122.68(15) ?
C4 C3 C2 . . 118.5(2) ?
C4 C3 H3 . . 120.8 ?
C2 C3 H3 . . 120.8 ?
C3 C4 C5 . . 120.6(2) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 121.3(2) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C1 . . 119.1(2) ?
C5 C6 H6 . . 120.5 ?
C1 C6 H6 . . 120.5 ?
S1 N1 Cl1 . . 110.56(9) ?
O1 Na1 O3 . . 82.14(6) ?
O1 Na1 O2 . 3_445 115.80(6) ?
O3 Na1 O2 . 3_445 156.33(6) ?
O1 Na1 O2 . 4_545 168.48(6) ?
O3 Na1 O2 . 4_545 86.38(6) ?
O2 Na1 O2 3_445 4_545 75.50(6) ?
O1 Na1 O4 . . 102.47(6) ?
O3 Na1 O4 . . 84.05(5) ?
O2 Na1 O4 3_445 . 77.23(5) ?
O2 Na1 O4 4_545 . 77.14(5) ?
O1 Na1 O3 . 4_545 85.97(6) ?
O3 Na1 O3 . 4_545 118.37(5) ?
O2 Na1 O3 3_445 4_545 79.99(5) ?
O2 Na1 O3 4_545 4_545 98.75(6) ?
O4 Na1 O3 . 4_545 157.17(5) ?
O1 Na1 S1 . 4_545 151.07(5) ?
O3 Na1 S1 . 4_545 79.85(4) ?
O2 Na1 S1 3_445 4_545 88.45(4) ?
O2 Na1 S1 4_545 4_545 22.58(3) ?
O4 Na1 S1 . 4_545 97.97(3) ?
O3 Na1 S1 4_545 4_545 82.95(4) ?
S1 O1 Na1 . . 154.80(9) ?
S1 O2 Na1 . 3 150.45(9) ?
S1 O2 Na1 . 4 116.06(8) ?
Na1 O2 Na1 3 4 89.02(5) ?
Na1 O3 Na1 . 4 111.04(6) ?
Na1 O3 H31 . . 121.4(19) ?
Na1 O3 H31 4 . 105.4(19) ?
Na1 O3 H32 . . 108.9(19) ?
Na1 O3 H32 4 . 102.1(19) ?
H31 O3 H32 . . 106(3) ?
Na1 O4 Na1 2 . 87.67(8) ?
Na1 O4 H41 2 . 109.7(18) ?
Na1 O4 H41 . . 125.3(18) ?
O2 S1 O1 . . 114.36(9) ?
O2 S1 N1 . . 105.17(8) ?
O1 S1 N1 . . 115.30(9) ?
O2 S1 C1 . . 107.39(9) ?
O1 S1 C1 . . 105.41(8) ?
N1 S1 C1 . . 108.91(8) ?
O2 S1 Na1 . 4 41.36(6) ?
O1 S1 Na1 . 4 73.08(6) ?
N1 S1 Na1 . 4 128.14(6) ?
C1 S1 Na1 . 4 117.93(6) ?
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 C6 . 1.376(3) ?
C1 C2 . 1.412(3) ?
C1 S1 . 1.7786(18) ?
C2 C3 . 1.377(3) ?
C2 Cl2 . 1.717(2) ?
C3 C4 . 1.372(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.389(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.374(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
Cl1 N1 . 1.7376(16) ?
N1 S1 . 1.5883(16) ?
Na1 O1 . 2.3785(15) ?
Na1 O3 . 2.4220(17) ?
Na1 O2 3_445 2.4710(15) ?
Na1 O2 4_545 2.4759(15) ?
Na1 O4 . 2.5035(18) ?
Na1 O3 4_545 2.5120(18) ?
Na1 S1 4_545 3.3661(9) ?
O1 S1 . 1.4562(14) ?
O2 S1 . 1.4390(14) ?
O2 Na1 3 2.4710(15) ?
O2 Na1 4 2.4759(15) ?
O3 Na1 4 2.5120(18) ?
O3 H31 . 0.792(16) ?
O3 H32 . 0.811(16) ?
O4 Na1 2 2.5035(18) ?
O4 H41 . 0.814(16) ?
S1 Na1 4 3.3661(9) ?
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 H31 N1 2_655 0.792(16) 2.151(17) 2.926(2) 166(3)
O3 H32 Cl1 4 0.811(16) 2.674(17) 3.4782(16) 171(2)
O4 H41 N1 4 0.814(16) 2.192(16) 3.005(2) 176(2)
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 . . . . -0.5(3) ?
S1 C1 C2 C3 . . . . -179.26(16) ?
C6 C1 C2 Cl2 . . . . 178.96(16) ?
S1 C1 C2 Cl2 . . . . 0.2(2) ?
C1 C2 C3 C4 . . . . -0.2(3) ?
Cl2 C2 C3 C4 . . . . -179.70(18) ?
C2 C3 C4 C5 . . . . 0.9(4) ?
C3 C4 C5 C6 . . . . -0.8(4) ?
C4 C5 C6 C1 . . . . 0.1(4) ?
C2 C1 C6 C5 . . . . 0.5(3) ?
S1 C1 C6 C5 . . . . 179.42(17) ?
O3 Na1 O1 S1 . . . . 50.3(2) ?
O2 Na1 O1 S1 3_445 . . . -145.9(2) ?
O2 Na1 O1 S1 4_545 . . . 45.6(5) ?
O4 Na1 O1 S1 . . . . 132.4(2) ?
O3 Na1 O1 S1 4_545 . . . -69.0(2) ?
S1 Na1 O1 S1 4_545 . . . -1.5(3) ?
O1 Na1 O3 Na1 . . . 4 31.28(6) ?
O2 Na1 O3 Na1 3_445 . . 4 -109.93(14) ?
O2 Na1 O3 Na1 4_545 . . 4 -149.66(7) ?
O4 Na1 O3 Na1 . . . 4 -72.23(6) ?
O3 Na1 O3 Na1 4_545 . . 4 112.35(9) ?
S1 Na1 O3 Na1 4_545 . . 4 -171.45(6) ?
O1 Na1 O4 Na1 . . . 2 152.95(5) ?
O3 Na1 O4 Na1 . . . 2 -126.49(5) ?
O2 Na1 O4 Na1 3_445 . . 2 38.93(4) ?
O2 Na1 O4 Na1 4_545 . . 2 -38.86(3) ?
O3 Na1 O4 Na1 4_545 . . 2 43.09(13) ?
S1 Na1 O4 Na1 4_545 . . 2 -47.647(17) ?
Na1 O2 S1 O1 3 . . . 141.67(17) ?
Na1 O2 S1 O1 4 . . . -3.82(12) ?
Na1 O2 S1 N1 3 . . . 14.2(2) ?
Na1 O2 S1 N1 4 . . . -131.33(9) ?
Na1 O2 S1 C1 3 . . . -101.75(18) ?
Na1 O2 S1 C1 4 . . . 112.77(9) ?
Na1 O2 S1 Na1 3 . . 4 145.5(2) ?
Na1 O1 S1 O2 . . . . -71.7(2) ?
Na1 O1 S1 N1 . . . . 50.4(3) ?
Na1 O1 S1 C1 . . . . 170.6(2) ?
Na1 O1 S1 Na1 . . . 4 -74.3(2) ?
Cl1 N1 S1 O2 . . . . -175.92(9) ?
Cl1 N1 S1 O1 . . . . 57.14(12) ?
Cl1 N1 S1 C1 . . . . -61.07(11) ?
Cl1 N1 S1 Na1 . . . 4 144.96(6) ?
C6 C1 S1 O2 . . . . -118.21(15) ?
C2 C1 S1 O2 . . . . 60.61(18) ?
C6 C1 S1 O1 . . . . 4.11(17) ?
C2 C1 S1 O1 . . . . -177.07(16) ?
C6 C1 S1 N1 . . . . 128.38(15) ?
C2 C1 S1 N1 . . . . -52.80(18) ?
C6 C1 S1 Na1 . . . 4 -74.61(16) ?
C2 C1 S1 Na1 . . . 4 104.21(15) ?
