##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-(2-Nitrophenylsulfonyl)-N-(4-nitrophenylsulfonyl)methylamine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H11 N3 O8 S2'
_chemical_formula_sum     'C13 H11 N3 O8 S2'
_chemical_formula_iupac     'C13 H11 N3 O8 S2'
_chemical_formula_weight     401.37
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_HALL     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     13.517(3)
_cell_length_b     9.994(2)
_cell_length_c     11.990(2)
_cell_angle_alpha     90.00
_cell_angle_beta     95.26(3)
_cell_angle_gamma     90.00
_cell_volume     1613.0(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     10014
_cell_measurement_theta_min     6.19
_cell_measurement_theta_max     54.95
_cell_measurement_temperature     153(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.58
_exptl_crystal_size_mid     0.47
_exptl_crystal_size_min     0.29
_exptl_crystal_density_diffrn     1.653
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     824
_exptl_absorpt_coefficient_mu     0.382
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(ABSCOR; Higashi 1995)'
_exptl_absorpt_correction_T_min     0.7499
_exptl_absorpt_correction_T_max     0.8970
_exptl_special_details
;
;
_diffrn_ambient_temperature     153(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Rotating Anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku R-AXIS RAPID IP area-detector'
_diffrn_measurement_method     'ω oscillation'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     15376
_diffrn_reflns_av_R_equivalents     0.0171
_diffrn_reflns_av_sigmaI/netI     0.0137
_diffrn_reflns_theta_min     3.03
_diffrn_reflns_theta_max     27.47
_diffrn_reflns_theta_full     27.47
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3683
_reflns_number_gt     3540
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0310
_refine_ls_R_factor_gt     0.0300
_refine_ls_wR_factor_gt     0.0932
_refine_ls_wR_factor_ref     0.0940
_refine_ls_goodness_of_fit_ref     1.125
_refine_ls_restrained_S_all     1.125
_refine_ls_number_reflns     3683
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0558P)²+0.7411P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.492
_refine_diff_density_min     -0.407
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2001)'
_refine_ls_extinction_coef     0.0231(18)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'RAPID-AUTO (Rigaku, 2004)'
_computing_cell_refinement     'RAPID-AUTO (Rigaku, 2004)'
_computing_data_reduction     'RAPID-AUTO (Rigaku, 2004)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 0.15312(2) 0.15728(3) 0.41897(3) 0.01644(11) Uani d . 1 . .
    S S2 0.35222(2) 0.06267(3) 0.48921(3) 0.01728(11) Uani d . 1 . .
    O O8 0.20741(8) 0.19778(11) 0.32804(8) 0.0220(2) Uani d . 1 . .
    O O7 0.06390(8) 0.08053(11) 0.39952(9) 0.0241(2) Uani d . 1 . .
    O O3 0.13493(10) 0.70583(13) 0.72576(12) 0.0399(3) Uani d . 1 . .
    O O6 0.39404(8) -0.02832(12) 0.57283(9) 0.0261(2) Uani d . 1 . .
    O O5 0.38943(8) 0.19667(11) 0.48792(9) 0.0255(2) Uani d . 1 . .
    O O4 -0.01529(9) 0.63329(11) 0.73325(9) 0.0271(2) Uani d . 1 . .
    N N3 0.23085(9) 0.06608(12) 0.50391(10) 0.0187(2) Uani d . 1 . .
    C C7 0.12748(10) 0.29709(13) 0.50127(11) 0.0161(3) Uani d . 1 . .
    O O2 0.34613(11) -0.36035(12) 0.39097(13) 0.0401(3) Uani d . 1 . .
    C C8 0.04276(10) 0.29488(13) 0.55885(11) 0.0173(3) Uani d . 1 . .
    H H8B -0.0011 0.2205 0.5523 0.021 Uiso calc R 1 . .
    N N1 0.31903(10) -0.24388(12) 0.39825(11) 0.0241(3) Uani d . 1 . .
    C C6 0.36282(10) -0.14363(14) 0.32761(12) 0.0199(3) Uani d . 1 . .
    C C11 0.17430(11) 0.51236(14) 0.57559(13) 0.0215(3) Uani d . 1 . .
    H H11A 0.2180 0.5870 0.5826 0.026 Uiso calc R 1 . .
    C C12 0.19373(10) 0.40442(15) 0.50825(12) 0.0209(3) Uani d . 1 . .
    H H12A 0.2509 0.4036 0.4677 0.025 Uiso calc R 1 . .
    C C4 0.40219(10) 0.08068(15) 0.27685(13) 0.0218(3) Uani d . 1 . .
    H H4A 0.4043 0.1739 0.2922 0.026 Uiso calc R 1 . .
    C C10 0.08951(10) 0.50856(13) 0.63249(11) 0.0177(3) Uani d . 1 . .
    C C5 0.36741(10) -0.00693(14) 0.35469(11) 0.0174(3) Uani d . 1 . .
    O O1 0.25661(11) -0.20743(12) 0.45856(12) 0.0375(3) Uani d . 1 . .
    C C9 0.02324(10) 0.40325(14) 0.62611(11) 0.0181(3) Uani d . 1 . .
    H H9A -0.0340 0.4048 0.6665 0.022 Uiso calc R 1 . .
    C C3 0.43385(11) 0.03367(18) 0.17699(13) 0.0269(3) Uani d . 1 . .
    H H3A 0.4561 0.0949 0.1241 0.032 Uiso calc R 1 . .
    N N2 0.06833(10) 0.62403(12) 0.70259(10) 0.0227(3) Uani d . 1 . .
    C C2 0.43303(12) -0.10224(18) 0.15451(13) 0.0286(3) Uani d . 1 . .
    H H2A 0.4578 -0.1345 0.0879 0.034 Uiso calc R 1 . .
    C C13 0.19287(12) 0.00944(17) 0.60575(13) 0.0268(3) Uani d . 1 . .
    H H13A 0.1205 0.0196 0.6011 0.040 Uiso calc R 1 . .
    H H13B 0.2229 0.0569 0.6719 0.040 Uiso calc R 1 . .
    H H13C 0.2100 -0.0857 0.6117 0.040 Uiso calc R 1 . .
    C C1 0.39611(11) -0.19141(16) 0.22913(13) 0.0258(3) Uani d . 1 . .
    H H1A 0.3937 -0.2844 0.2129 0.031 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O8 . 1.4275(11) ?
    S1 O7 . 1.4304(11) ?
    S1 N3 . 1.6660(13) ?
    S1 C7 . 1.7633(14) ?
    S2 O6 . 1.4310(11) ?
    S2 O5 . 1.4312(11) ?
    S2 N3 . 1.6665(13) ?
    S2 C5 . 1.7855(14) ?
    O3 N2 . 1.2289(19) ?
    O4 N2 . 1.2236(18) ?
    N3 C13 . 1.4799(18) ?
    C7 C8 . 1.3905(19) ?
    C7 C12 . 1.3950(19) ?
    O2 N1 . 1.2258(17) ?
    C8 C9 . 1.3901(19) ?
    C8 H8B . 0.9500 ?
    N1 O1 . 1.2164(18) ?
    N1 C6 . 1.4709(19) ?
    C6 C1 . 1.387(2) ?
    C6 C5 . 1.4044(19) ?
    C11 C12 . 1.387(2) ?
    C11 C10 . 1.387(2) ?
    C11 H11A . 0.9500 ?
    C12 H12A . 0.9500 ?
    C4 C3 . 1.390(2) ?
    C4 C5 . 1.393(2) ?
    C4 H4A . 0.9500 ?
    C10 C9 . 1.380(2) ?
    C10 N2 . 1.4712(17) ?
    C9 H9A . 0.9500 ?
    C3 C2 . 1.385(2) ?
    C3 H3A . 0.9500 ?
    C2 C1 . 1.388(2) ?
    C2 H2A . 0.9500 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C1 H1A . 0.9500 ?
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
    O8 S1 O7 . . 120.82(7) ?
    O8 S1 N3 . . 106.41(6) ?
    O7 S1 N3 . . 106.34(7) ?
    O8 S1 C7 . . 110.12(7) ?
    O7 S1 C7 . . 108.07(7) ?
    N3 S1 C7 . . 103.69(6) ?
    O6 S2 O5 . . 119.05(7) ?
    O6 S2 N3 . . 105.57(7) ?
    O5 S2 N3 . . 109.41(6) ?
    O6 S2 C5 . . 108.34(7) ?
    O5 S2 C5 . . 106.57(7) ?
    N3 S2 C5 . . 107.42(7) ?
    C13 N3 S1 . . 117.82(10) ?
    C13 N3 S2 . . 119.92(10) ?
    S1 N3 S2 . . 121.22(7) ?
    C8 C7 C12 . . 122.40(12) ?
    C8 C7 S1 . . 118.58(10) ?
    C12 C7 S1 . . 119.00(10) ?
    C9 C8 C7 . . 118.98(13) ?
    C9 C8 H8B . . 120.5 ?
    C7 C8 H8B . . 120.5 ?
    O1 N1 O2 . . 123.70(14) ?
    O1 N1 C6 . . 118.43(12) ?
    O2 N1 C6 . . 117.85(13) ?
    C1 C6 C5 . . 121.40(14) ?
    C1 C6 N1 . . 115.78(13) ?
    C5 C6 N1 . . 122.76(13) ?
    C12 C11 C10 . . 118.30(13) ?
    C12 C11 H11A . . 120.8 ?
    C10 C11 H11A . . 120.8 ?
    C11 C12 C7 . . 118.57(13) ?
    C11 C12 H12A . . 120.7 ?
    C7 C12 H12A . . 120.7 ?
    C3 C4 C5 . . 120.96(14) ?
    C3 C4 H4A . . 119.5 ?
    C5 C4 H4A . . 119.5 ?
    C9 C10 C11 . . 123.72(13) ?
    C9 C10 N2 . . 118.08(13) ?
    C11 C10 N2 . . 118.20(13) ?
    C4 C5 C6 . . 117.85(13) ?
    C4 C5 S2 . . 115.74(11) ?
    C6 C5 S2 . . 125.56(11) ?
    C10 C9 C8 . . 118.02(13) ?
    C10 C9 H9A . . 121.0 ?
    C8 C9 H9A . . 121.0 ?
    C2 C3 C4 . . 120.11(15) ?
    C2 C3 H3A . . 119.9 ?
    C4 C3 H3A . . 119.9 ?
    O4 N2 O3 . . 124.02(13) ?
    O4 N2 C10 . . 117.68(12) ?
    O3 N2 C10 . . 118.30(13) ?
    C3 C2 C1 . . 120.10(14) ?
    C3 C2 H2A . . 120.0 ?
    C1 C2 H2A . . 120.0 ?
    N3 C13 H13A . . 109.5 ?
    N3 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    N3 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C6 C1 C2 . . 119.47(15) ?
    C6 C1 H1A . . 120.3 ?
    C2 C1 H1A . . 120.3 ?
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
    O8 S1 N3 C13 . . . . -179.35(11) ?
    O7 S1 N3 C13 . . . . -49.34(12) ?
    C7 S1 N3 C13 . . . . 64.50(12) ?
    O8 S1 N3 S2 . . . . 12.32(10) ?
    O7 S1 N3 S2 . . . . 142.33(8) ?
    C7 S1 N3 S2 . . . . -103.84(9) ?
    O6 S2 N3 C13 . . . . 13.90(13) ?
    O5 S2 N3 C13 . . . . -115.35(12) ?
    C5 S2 N3 C13 . . . . 129.34(12) ?
    O6 S2 N3 S1 . . . . -178.01(8) ?
    O5 S2 N3 S1 . . . . 52.74(10) ?
    C5 S2 N3 S1 . . . . -62.56(10) ?
    O8 S1 C7 C8 . . . . 151.35(11) ?
    O7 S1 C7 C8 . . . . 17.44(13) ?
    N3 S1 C7 C8 . . . . -95.14(12) ?
    O8 S1 C7 C12 . . . . -30.00(13) ?
    O7 S1 C7 C12 . . . . -163.91(11) ?
    N3 S1 C7 C12 . . . . 83.51(12) ?
    C12 C7 C8 C9 . . . . -0.2(2) ?
    S1 C7 C8 C9 . . . . 178.44(10) ?
    O1 N1 C6 C1 . . . . -152.05(15) ?
    O2 N1 C6 C1 . . . . 26.4(2) ?
    O1 N1 C6 C5 . . . . 25.4(2) ?
    O2 N1 C6 C5 . . . . -156.21(15) ?
    C10 C11 C12 C7 . . . . -0.3(2) ?
    C8 C7 C12 C11 . . . . 0.3(2) ?
    S1 C7 C12 C11 . . . . -178.29(11) ?
    C12 C11 C10 C9 . . . . 0.1(2) ?
    C12 C11 C10 N2 . . . . -179.14(12) ?
    C3 C4 C5 C6 . . . . -1.7(2) ?
    C3 C4 C5 S2 . . . . 168.34(11) ?
    C1 C6 C5 C4 . . . . 3.0(2) ?
    N1 C6 C5 C4 . . . . -174.28(13) ?
    C1 C6 C5 S2 . . . . -165.97(11) ?
    N1 C6 C5 S2 . . . . 16.74(19) ?
    O6 S2 C5 C4 . . . . -134.24(11) ?
    O5 S2 C5 C4 . . . . -5.02(12) ?
    N3 S2 C5 C4 . . . . 112.16(11) ?
    O6 S2 C5 C6 . . . . 34.94(14) ?
    O5 S2 C5 C6 . . . . 164.17(12) ?
    N3 S2 C5 C6 . . . . -78.65(13) ?
    C11 C10 C9 C8 . . . . 0.0(2) ?
    N2 C10 C9 C8 . . . . 179.28(11) ?
    C7 C8 C9 C10 . . . . -0.02(19) ?
    C5 C4 C3 C2 . . . . -1.3(2) ?
    C9 C10 N2 O4 . . . . -14.29(18) ?
    C11 C10 N2 O4 . . . . 164.99(13) ?
    C9 C10 N2 O3 . . . . 166.50(14) ?
    C11 C10 N2 O3 . . . . -14.22(19) ?
    C4 C3 C2 C1 . . . . 3.1(2) ?
    C5 C6 C1 C2 . . . . -1.3(2) ?
    N1 C6 C1 C2 . . . . 176.21(13) ?
    C3 C2 C1 C6 . . . . -1.8(2) ?
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
    C8 H8B O7 . 0.95 2.53 2.902(2) 103.7
    C4 H4A O5 . 0.95 2.38 2.803(2) 106.3
    C13 H13A O7 . 0.98 2.54 2.978(2) 106.9
    C13 H13C O1 . 0.98 2.34 2.972(2) 121.8
    C1 H1A O6 4 0.95 2.51 3.369(2) 149.7
data_global
_journal_date_recd_electronic     2008-07-22
_journal_date_accepted     2008-08-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     10
_journal_page_first     o1885
_journal_page_last     o1885
_journal_paper_category     QO
_journal_coeditor_code     RZ2239
_publ_contact_author_name     'Dr Haiyan Lu'
_publ_contact_author_address
;
The Graduate School of the Chinese Academy of Sciences,
Beijing 100049,
People's Republic of China
;
_publ_contact_author_email     haiyan_lu2008@yahoo.cn
_publ_contact_author_fax     '+86-532-84023405'
_publ_contact_author_phone     '+86-532-84023405'
_publ_section_title
;
N-(2-Nitrophenylsulfonyl)-N-(4-nitrophenylsulfonyl)methylamine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Haiyan Lu' .
;
The Graduate School of the Chinese Academy of Sciences,
Beijing 100049,
People's Republic of China
;
