#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007170.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_2007170
loop_
_publ_author_name
'Moers, O.'
'Jones, P. G.'
'Blaschette, A.'
_publ_section_title
;
 Polysulfonylamines. C. Bis(4-nitrobenzenesulfonyl)amine Monohydrate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              504
_journal_page_last               507
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C12 H9 N3 O8 S2 , H2 O1'
_chemical_formula_sum            'C12 H11 N3 O9 S2'
_chemical_formula_weight         405.36
_chemical_name_systematic
;
 Di(4-nitrobenzenesulfonyl)amine Monohydrate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.558(4)
_cell_length_b                   5.4771(15)
_cell_length_c                   23.207(5)
_cell_measurement_reflns_used    62
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     1596.2(8)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS (Fait, 1991)'
_computing_data_reduction        'Siemens XSCANS'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'omega 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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            3069
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.24
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 247
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.391
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.191
_refine_ls_abs_structure_details 'Flack  (1983) parameter = 0.36(7)'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.063
_refine_ls_goodness_of_fit_obs   1.114
_refine_ls_hydrogen_treatment    H_atoms:_see_below
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_restrained_S_obs      1.114
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_obs          0.0323
_refine_ls_shift/esd_max         0.005
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0403P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0740
_refine_ls_wR_factor_obs         0.0724
_reflns_number_observed          2495
_reflns_number_total             2821
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fg1400.cif
_[local]_cod_data_source_block   dolan
_cod_original_cell_volume        1596.2(7)
_cod_database_code               2007170
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'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0139(13) 0.0225(14) 0.0220(14) 0.0037(12) 0.0038(11) -0.0024(11)
S1 0.0238(4) 0.0172(3) 0.0225(4) -0.0021(3) 0.0038(4) 0.0008(4)
O1 0.0426(16) 0.0260(13) 0.0293(13) 0.0059(12) 0.0052(12) 0.0073(11)
O2 0.0288(12) 0.0294(13) 0.0305(12) -0.0092(11) 0.0060(11) -0.0097(10)
S2 0.0128(3) 0.0148(3) 0.0209(3) -0.0003(3) 0.0017(3) -0.0015(3)
O5 0.0167(11) 0.0213(11) 0.0312(12) -0.0055(10) 0.0029(9) -0.0007(10)
O6 0.0200(11) 0.0214(12) 0.0326(13) 0.0024(10) -0.0006(10) -0.0070(10)
N2 0.0406(18) 0.0231(15) 0.0288(17) -0.0082(15) 0.0147(15) 0.0012(13)
O3 0.0457(16) 0.0405(16) 0.0387(15) -0.0200(14) 0.0096(13) -0.0175(13)
O4 0.0572(18) 0.0343(15) 0.0446(15) 0.0121(15) 0.0134(14) -0.0047(13)
N3 0.0228(15) 0.0241(15) 0.0244(14) -0.0005(13) -0.0013(12) -0.0004(12)
O7 0.0292(13) 0.0364(15) 0.0361(15) -0.0150(12) 0.0021(11) -0.0057(12)
O8 0.0262(14) 0.0466(16) 0.0361(14) -0.0013(13) 0.0008(11) -0.0202(13)
C1 0.0261(16) 0.0193(16) 0.0168(15) -0.0012(14) 0.0061(13) 0.0019(13)
C2 0.0245(17) 0.0276(19) 0.0210(15) -0.0018(15) 0.0010(13) -0.0025(14)
C3 0.0234(17) 0.0324(19) 0.0276(17) 0.0013(15) 0.0043(15) 0.0018(16)
C4 0.0321(18) 0.0177(15) 0.0225(15) -0.0043(15) 0.0116(15) 0.0004(14)
C5 0.0327(19) 0.0308(19) 0.0152(16) -0.0054(16) 0.0009(15) -0.0010(14)
C6 0.0233(17) 0.0273(17) 0.0192(15) -0.0008(15) 0.0017(14) 0.0038(14)
C7 0.0154(15) 0.0163(14) 0.0156(15) -0.0013(13) -0.0010(12) 0.0016(12)
C8 0.0128(14) 0.0249(17) 0.0257(17) 0.0023(14) 0.0039(13) -0.0040(14)
C9 0.0159(16) 0.0288(18) 0.0260(17) 0.0009(15) -0.0019(13) -0.0005(15)
C10 0.0216(16) 0.0192(16) 0.0165(14) -0.0017(13) -0.0004(13) 0.0011(13)
C11 0.0180(16) 0.0240(17) 0.0232(17) 0.0023(14) 0.0010(13) -0.0054(14)
C12 0.0142(16) 0.0283(17) 0.0214(15) 0.0007(13) -0.0003(13) -0.0015(15)
O1W 0.0140(11) 0.0232(14) 0.0532(16) 0.0009(11) -0.0036(11) -0.0096(12)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
N1 0.7156(2) 0.3097(5) 0.19916(11) 0.0195(6) Uani d . 1 N
H01 0.664(3) 0.394(6) 0.2027(13) 0.016(9) Uiso d . 1 H
S1 0.80272(6) 0.43590(13) 0.15330(4) 0.02114(18) Uani d . 1 S
O1 0.7389(2) 0.6119(4) 0.12394(10) 0.0327(6) Uani d . 1 O
O2 0.89753(18) 0.5042(4) 0.18339(10) 0.0295(5) Uani d . 1 O
S2 0.74927(6) 0.14487(13) 0.25544(4) 0.01618(16) Uani d . 1 S
O5 0.64999(17) 0.0477(4) 0.27642(9) 0.0231(5) Uani d . 1 O
O6 0.83232(17) -0.0165(4) 0.23717(10) 0.0247(5) Uani d . 1 O
N2 0.9258(3) -0.3529(5) -0.01087(12) 0.0309(7) Uani d . 1 N
O3 0.8677(2) -0.3947(5) -0.05172(12) 0.0417(7) Uani d . 1 O
O4 1.0091(2) -0.4647(5) -0.00079(11) 0.0454(7) Uani d . 1 O
N3 0.9165(2) 0.8709(5) 0.42317(11) 0.0237(6) Uani d . 1 N
O7 1.0076(2) 0.9472(5) 0.41447(9) 0.0339(6) Uani d . 1 O
O8 0.85865(19) 0.9441(5) 0.46227(10) 0.0363(6) Uani d . 1 O
C1 0.8376(3) 0.2004(6) 0.10468(12) 0.0207(7) Uani d . 1 C
C2 0.9394(3) 0.1009(6) 0.10793(14) 0.0243(7) Uani d . 1 C
H2 0.9883 0.1579 0.1361 0.029 Uiso calc R 1 H
C3 0.9691(3) -0.0811(7) 0.06996(14) 0.0278(8) Uani d . 1 C
H3 1.0377 -0.1537 0.0719 0.033 Uiso calc R 1 H
C4 0.8960(3) -0.1539(6) 0.02913(14) 0.0241(7) Uani d . 1 C
C5 0.7948(3) -0.0541(6) 0.02439(13) 0.0262(8) Uani d . 1 C
H5 0.7470 -0.1086 -0.0046 0.031 Uiso calc R 1 H
C6 0.7651(3) 0.1257(6) 0.06266(13) 0.0233(7) Uani d . 1 C
H6 0.6964 0.1977 0.0605 0.028 Uiso calc R 1 H
C7 0.7984(2) 0.3481(5) 0.30783(12) 0.0158(6) Uani d . 1 C
C8 0.9083(2) 0.3772(6) 0.31305(14) 0.0212(7) Uani d . 1 C
H8 0.9557 0.2814 0.2906 0.025 Uiso calc R 1 H
C9 0.9470(3) 0.5490(6) 0.35180(14) 0.0236(7) Uani d . 1 C
H9 1.0215 0.5742 0.3561 0.028 Uiso calc R 1 H
C10 0.8754(2) 0.6819(6) 0.38384(13) 0.0191(7) Uani d . 1 C
C11 0.7656(3) 0.6504(6) 0.38027(14) 0.0218(7) Uani d . 1 C
H11 0.7187 0.7428 0.4038 0.026 Uiso calc R 1 H
C12 0.7268(3) 0.4796(6) 0.34128(14) 0.0213(7) Uani d . 1 C
H12 0.6523 0.4532 0.3376 0.026 Uiso calc R 1 H
O1W 0.55479(19) 0.6082(5) 0.23320(12) 0.0302(6) Uani d . 1 O
H02 0.574(3) 0.745(8) 0.2419(15) 0.031(11) Uiso d . 1 H
H03 0.498(5) 0.623(10) 0.222(2) 0.099(16) Uiso d . 1 H
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
_geom_angle_publ_flag
S2 N1 S1 124.34(17) y
O1 S1 O2 121.61(16) y
O1 S1 N1 102.45(14) y
O2 S1 N1 109.95(14) y
O1 S1 C1 109.09(15) y
O2 S1 C1 107.23(15) y
N1 S1 C1 105.43(14) y
O6 S2 O5 120.18(13) y
O6 S2 N1 106.92(14) y
O5 S2 N1 104.44(13) y
O6 S2 C7 109.87(14) y
O5 S2 C7 107.66(14) y
N1 S2 C7 106.96(13) y
O3 N2 O4 124.2(3) y
O3 N2 C4 118.4(3) ?
O4 N2 C4 117.4(3) ?
O8 N3 O7 123.9(3) y
O8 N3 C10 118.6(3) ?
O7 N3 C10 117.5(3) ?
C2 C1 C6 121.5(3) ?
C2 C1 S1 118.6(2) ?
C6 C1 S1 119.9(2) ?
C3 C2 C1 119.7(3) ?
C4 C3 C2 117.9(3) ?
C3 C4 C5 123.4(3) ?
C3 C4 N2 118.5(3) ?
C5 C4 N2 118.1(3) ?
C6 C5 C4 118.5(3) ?
C5 C6 C1 119.0(3) ?
C12 C7 C8 122.2(3) ?
C12 C7 S2 119.2(2) ?
C8 C7 S2 118.6(2) ?
C9 C8 C7 118.7(3) ?
C10 C9 C8 118.6(3) ?
C9 C10 C11 123.4(3) ?
C9 C10 N3 118.5(3) ?
C11 C10 N3 118.1(3) ?
C12 C11 C10 118.1(3) ?
C7 C12 C11 119.0(3) ?
H01 N1 S1 111(2) y
H01 N1 S2 116(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 S2 1.643(3) y
N1 S1 1.675(3) y
S1 O1 1.427(2) y
S1 O2 1.430(2) y
S1 C1 1.769(3) y
S2 O6 1.431(2) y
S2 O5 1.440(2) y
S2 C7 1.760(3) y
N2 O3 1.218(4) y
N2 O4 1.235(4) y
N2 C4 1.479(4) ?
N3 O8 1.229(3) y
N3 O7 1.236(3) y
N3 C10 1.473(4) ?
C1 C2 1.392(5) ?
C1 C6 1.395(4) ?
C2 C3 1.382(5) ?
C3 C4 1.378(5) ?
C4 C5 1.388(5) ?
C5 C6 1.377(5) ?
C7 C12 1.389(4) ?
C7 C8 1.395(4) ?
C8 C9 1.390(5) ?
C9 C10 1.376(4) ?
C10 C11 1.391(4) ?
C11 C12 1.390(5) ?
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
_geom_hbond_publ_flag
N1 H01 O1W . 0.80(3) 1.94(3) 2.716(4) 163(3) y
O1W H02 O5 1_565 0.81(4) 2.07(4) 2.869(4) 166(4) y
O1W H03 O6 3_455 0.77(6) 2.18(6) 2.840(3) 144(6) y
O1W H03 O2 3_465 0.77(6) 2.56(6) 3.122(3) 131(5) y
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_publ_flag
S2 N1 S1 O1 -163.65(19) y
S2 N1 S1 O2 -33.0(2) y
S2 N1 S1 C1 82.2(2) y
S1 N1 S2 O6 -43.5(2) y
S1 N1 S2 O5 -171.84(18) y
S1 N1 S2 C7 74.2(2) y
O1 S1 C1 C2 141.5(2) ?
O2 S1 C1 C2 8.1(3) ?
N1 S1 C1 C2 -109.1(3) ?
O1 S1 C1 C6 -35.7(3) ?
O2 S1 C1 C6 -169.2(2) ?
N1 S1 C1 C6 73.7(3) ?
C6 C1 C2 C3 -1.9(5) ?
S1 C1 C2 C3 -179.2(2) ?
C1 C2 C3 C4 1.3(5) ?
C2 C3 C4 C5 -0.1(5) ?
C2 C3 C4 N2 -178.5(3) ?
O3 N2 C4 C3 -170.1(3) ?
O4 N2 C4 C3 9.2(4) ?
O3 N2 C4 C5 11.4(4) ?
O4 N2 C4 C5 -169.3(3) ?
C3 C4 C5 C6 -0.5(5) ?
N2 C4 C5 C6 177.9(3) ?
C4 C5 C6 C1 -0.1(5) ?
C2 C1 C6 C5 1.3(5) ?
S1 C1 C6 C5 178.5(2) ?
O6 S2 C7 C12 -164.6(2) ?
O5 S2 C7 C12 -32.0(3) ?
N1 S2 C7 C12 79.7(3) ?
O6 S2 C7 C8 17.4(3) ?
O5 S2 C7 C8 150.0(2) ?
N1 S2 C7 C8 -98.3(3) ?
C12 C7 C8 C9 -2.0(5) ?
S2 C7 C8 C9 175.9(2) ?
C7 C8 C9 C10 0.6(5) ?
C8 C9 C10 C11 1.2(5) ?
C8 C9 C10 N3 -177.6(3) ?
O8 N3 C10 C9 -161.0(3) ?
O7 N3 C10 C9 19.4(4) ?
O8 N3 C10 C11 20.2(4) ?
O7 N3 C10 C11 -159.5(3) ?
C9 C10 C11 C12 -1.6(5) ?
N3 C10 C11 C12 177.2(3) ?
C8 C7 C12 C11 1.6(5) ?
S2 C7 C12 C11 -176.3(2) ?
C10 C11 C12 C7 0.1(5) ?