##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N,N-Bis(5-bromo-2-thienylsulfonyl)-3-nitroaniline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H8 Br2 N2 O6 S4'
_chemical_formula_sum     'C14 H8 Br2 N2 O6 S4'
_chemical_formula_iupac     'C14 H8 Br2 N2 O6 S4'
_chemical_formula_weight     588.30
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.5147(7)
_cell_length_b     9.3674(7)
_cell_length_c     13.7585(11)
_cell_angle_alpha     103.1090(10)
_cell_angle_beta     100.8100(10)
_cell_angle_gamma     105.1550(10)
_cell_volume     995.42(14)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2347
_cell_measurement_theta_min     2.36
_cell_measurement_theta_max     24.97
_cell_measurement_temperature     298(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.29
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.963
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     576
_exptl_absorpt_coefficient_mu     4.526
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2002)'
_exptl_absorpt_correction_T_min     0.2936
_exptl_absorpt_correction_T_max     0.3919
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5264
_diffrn_reflns_av_R_equivalents     0.0132
_diffrn_reflns_av_sigmaI/netI     0.0321
_diffrn_reflns_theta_min     2.35
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.985
_diffrn_measured_fraction_theta_full     0.985
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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     3451
_reflns_number_gt     2895
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0436
_refine_ls_R_factor_gt     0.0356
_refine_ls_wR_factor_gt     0.0901
_refine_ls_wR_factor_ref     0.0952
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     3451
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0448P)²+1.0353P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.574
_refine_diff_density_min     -0.504
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Br' 'Br' -0.2901 2.4595
                         '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     'SMART (Bruker, 2002)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2002)'
_computing_publication_material     'SHELXL97'
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
    Br Br1 0.80658(6) 0.57752(6) -0.01657(3) 0.06367(16) Uani d . 1 . .
    Br Br2 0.16643(7) 0.79432(6) 0.73552(3) 0.06776(17) Uani d . 1 . .
    S S1 0.70495(14) 0.75108(11) 0.16962(8) 0.0508(3) Uani d . 1 . .
    S S2 0.56667(11) 0.75343(11) 0.35446(7) 0.0415(2) Uani d . 1 . .
    S S3 0.19996(11) 0.59462(10) 0.30359(7) 0.0402(2) Uani d . 1 . .
    S S4 0.24634(15) 0.65019(13) 0.53339(8) 0.0549(3) Uani d . 1 . .
    O O1 0.6610(3) 0.9124(3) 0.3806(2) 0.0577(7) Uani d . 1 . .
    O O2 0.5703(4) 0.6730(3) 0.4300(2) 0.0583(7) Uani d . 1 . .
    O O3 0.0704(3) 0.5875(3) 0.2195(2) 0.0554(7) Uani d . 1 . .
    O O4 0.2608(4) 0.4679(3) 0.3058(2) 0.0553(7) Uani d . 1 . .
    O O5 0.2349(8) 0.8484(5) -0.0312(3) 0.141(2) Uani d . 1 . .
    O O6 0.2078(12) 1.0655(7) -0.0019(4) 0.220(4) Uani d . 1 . .
    N N1 0.3660(4) 0.7446(3) 0.3097(2) 0.0377(6) Uani d . 1 . .
    N N2 0.2335(8) 0.9620(5) 0.0268(3) 0.1021(18) Uani d . 1 . .
    C C1 0.7121(5) 0.5809(5) 0.0948(3) 0.0462(9) Uani d . 1 . .
    C C2 0.6533(5) 0.4597(5) 0.1300(3) 0.0544(10) Uani d . 1 . .
    H H2 0.6492 0.3593 0.0987 0.065 Uiso calc R 1 . .
    C C3 0.5988(5) 0.5025(5) 0.2192(3) 0.0521(10) Uani d . 1 . .
    H H3 0.5536 0.4337 0.2536 0.062 Uiso calc R 1 . .
    C C4 0.6197(4) 0.6552(4) 0.2491(3) 0.0412(8) Uani d . 1 . .
    C C5 0.3332(4) 0.8701(4) 0.2738(3) 0.0389(8) Uani d . 1 . .
    C C6 0.3002(5) 0.8562(4) 0.1699(3) 0.0489(9) Uani d . 1 . .
    H H6 0.3000 0.7679 0.1224 0.059 Uiso calc R 1 . .
    C C7 0.2675(7) 0.9768(5) 0.1384(3) 0.0620(12) Uani d . 1 . .
    C C8 0.2669(6) 1.1098(5) 0.2055(3) 0.0618(12) Uani d . 1 . .
    H H8 0.2449 1.1897 0.1815 0.074 Uiso calc R 1 . .
    C C9 0.2998(6) 1.1209(5) 0.3093(3) 0.0565(11) Uani d . 1 . .
    H H9 0.2993 1.2093 0.3564 0.068 Uiso calc R 1 . .
    C C10 0.3337(5) 1.0025(4) 0.3444(3) 0.0472(9) Uani d . 1 . .
    H H10 0.3566 1.0112 0.4147 0.057 Uiso calc R 1 . .
    C C11 0.1428(4) 0.6570(4) 0.4158(3) 0.0408(8) Uani d . 1 . .
    C C12 0.0271(5) 0.7303(5) 0.4243(3) 0.0580(11) Uani d . 1 . .
    H H12 -0.0394 0.7456 0.3683 0.070 Uiso calc R 1 . .
    C C13 0.0170(5) 0.7811(6) 0.5264(3) 0.0619(11) Uani d . 1 . .
    H H13 -0.0566 0.8329 0.5460 0.074 Uiso calc R 1 . .
    C C14 0.1281(5) 0.7448(4) 0.5924(3) 0.0482(9) Uani d . 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
    Br1 C1 . 1.857(4) ?
    Br2 C14 . 1.861(4) ?
    S1 C4 . 1.713(4) ?
    S1 C1 . 1.713(4) ?
    S2 O2 . 1.415(3) ?
    S2 O1 . 1.420(3) ?
    S2 N1 . 1.677(3) ?
    S2 C4 . 1.735(4) ?
    S3 O3 . 1.417(3) ?
    S3 O4 . 1.417(3) ?
    S3 N1 . 1.686(3) ?
    S3 C11 . 1.727(4) ?
    S4 C14 . 1.704(4) ?
    S4 C11 . 1.715(4) ?
    O5 N2 . 1.181(5) ?
    O6 N2 . 1.182(5) ?
    N1 C5 . 1.444(4) ?
    N2 C7 . 1.475(6) ?
    C1 C2 . 1.348(6) ?
    C2 C3 . 1.404(6) ?
    C2 H2 . 0.930 ?
    C3 C4 . 1.349(5) ?
    C3 H3 . 0.930 ?
    C5 C6 . 1.374(5) ?
    C5 C10 . 1.389(5) ?
    C6 C7 . 1.372(5) ?
    C6 H6 . 0.930 ?
    C7 C8 . 1.374(6) ?
    C8 C9 . 1.378(6) ?
    C8 H8 . 0.930 ?
    C9 C10 . 1.380(5) ?
    C9 H9 . 0.930 ?
    C10 H10 . 0.930 ?
    C11 C12 . 1.348(5) ?
    C12 C13 . 1.404(6) ?
    C12 H12 . 0.930 ?
    C13 C14 . 1.349(6) ?
    C13 H13 . 0.930 ?
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
    C4 S1 C1 . . 89.88(19) ?
    O2 S2 O1 . . 120.68(18) ?
    O2 S2 N1 . . 107.56(16) ?
    O1 S2 N1 . . 104.87(16) ?
    O2 S2 C4 . . 109.33(18) ?
    O1 S2 C4 . . 107.98(18) ?
    N1 S2 C4 . . 105.36(16) ?
    O3 S3 O4 . . 121.60(18) ?
    O3 S3 N1 . . 105.18(16) ?
    O4 S3 N1 . . 106.70(16) ?
    O3 S3 C11 . . 107.58(18) ?
    O4 S3 C11 . . 110.68(17) ?
    N1 S3 C11 . . 103.50(16) ?
    C14 S4 C11 . . 90.14(19) ?
    C5 N1 S2 . . 118.8(2) ?
    C5 N1 S3 . . 118.3(2) ?
    S2 N1 S3 . . 122.91(17) ?
    O5 N2 O6 . . 121.7(5) ?
    O5 N2 C7 . . 119.4(4) ?
    O6 N2 C7 . . 118.9(4) ?
    C2 C1 S1 . . 112.9(3) ?
    C2 C1 Br1 . . 126.3(3) ?
    S1 C1 Br1 . . 120.7(2) ?
    C1 C2 C3 . . 112.2(4) ?
    C1 C2 H2 . . 123.9 ?
    C3 C2 H2 . . 123.9 ?
    C4 C3 C2 . . 112.0(4) ?
    C4 C3 H3 . . 124.0 ?
    C2 C3 H3 . . 124.0 ?
    C3 C4 S1 . . 113.0(3) ?
    C3 C4 S2 . . 126.4(3) ?
    S1 C4 S2 . . 120.6(2) ?
    C6 C5 C10 . . 120.7(3) ?
    C6 C5 N1 . . 119.4(3) ?
    C10 C5 N1 . . 119.9(3) ?
    C7 C6 C5 . . 117.9(3) ?
    C7 C6 H6 . . 121.1 ?
    C5 C6 H6 . . 121.1 ?
    C6 C7 C8 . . 123.3(4) ?
    C6 C7 N2 . . 117.7(4) ?
    C8 C7 N2 . . 119.0(4) ?
    C7 C8 C9 . . 117.8(4) ?
    C7 C8 H8 . . 121.1 ?
    C9 C8 H8 . . 121.1 ?
    C8 C9 C10 . . 120.8(3) ?
    C8 C9 H9 . . 119.6 ?
    C10 C9 H9 . . 119.6 ?
    C9 C10 C5 . . 119.5(4) ?
    C9 C10 H10 . . 120.3 ?
    C5 C10 H10 . . 120.3 ?
    C12 C11 S4 . . 112.0(3) ?
    C12 C11 S3 . . 125.2(3) ?
    S4 C11 S3 . . 122.5(2) ?
    C11 C12 C13 . . 113.2(4) ?
    C11 C12 H12 . . 123.4 ?
    C13 C12 H12 . . 123.4 ?
    C14 C13 C12 . . 111.1(4) ?
    C14 C13 H13 . . 124.4 ?
    C12 C13 H13 . . 124.4 ?
    C13 C14 S4 . . 113.5(3) ?
    C13 C14 Br2 . . 126.8(3) ?
    S4 C14 Br2 . . 119.7(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
    O2 S2 N1 C5 . . . . 149.9(3) ?
    O1 S2 N1 C5 . . . . 20.3(3) ?
    C4 S2 N1 C5 . . . . -93.5(3) ?
    O2 S2 N1 S3 . . . . -30.6(3) ?
    O1 S2 N1 S3 . . . . -160.2(2) ?
    C4 S2 N1 S3 . . . . 86.0(2) ?
    O3 S3 N1 C5 . . . . 28.7(3) ?
    O4 S3 N1 C5 . . . . 159.1(3) ?
    C11 S3 N1 C5 . . . . -84.1(3) ?
    O3 S3 N1 S2 . . . . -150.8(2) ?
    O4 S3 N1 S2 . . . . -20.4(3) ?
    C11 S3 N1 S2 . . . . 96.4(2) ?
    C4 S1 C1 C2 . . . . -0.3(3) ?
    C4 S1 C1 Br1 . . . . -176.5(2) ?
    S1 C1 C2 C3 . . . . 0.6(5) ?
    Br1 C1 C2 C3 . . . . 176.5(3) ?
    C1 C2 C3 C4 . . . . -0.6(5) ?
    C2 C3 C4 S1 . . . . 0.3(4) ?
    C2 C3 C4 S2 . . . . 179.4(3) ?
    C1 S1 C4 C3 . . . . 0.0(3) ?
    C1 S1 C4 S2 . . . . -179.1(2) ?
    O2 S2 C4 C3 . . . . 26.3(4) ?
    O1 S2 C4 C3 . . . . 159.3(3) ?
    N1 S2 C4 C3 . . . . -89.1(4) ?
    O2 S2 C4 S1 . . . . -154.7(2) ?
    O1 S2 C4 S1 . . . . -21.7(3) ?
    N1 S2 C4 S1 . . . . 90.0(2) ?
    S2 N1 C5 C6 . . . . 97.4(4) ?
    S3 N1 C5 C6 . . . . -82.1(4) ?
    S2 N1 C5 C10 . . . . -83.2(4) ?
    S3 N1 C5 C10 . . . . 97.3(4) ?
    C10 C5 C6 C7 . . . . -0.1(6) ?
    N1 C5 C6 C7 . . . . 179.2(4) ?
    C5 C6 C7 C8 . . . . 0.2(7) ?
    C5 C6 C7 N2 . . . . 179.5(5) ?
    O5 N2 C7 C6 . . . . 0.2(9) ?
    O6 N2 C7 C6 . . . . -178.8(7) ?
    O5 N2 C7 C8 . . . . 179.5(6) ?
    O6 N2 C7 C8 . . . . 0.5(10) ?
    C6 C7 C8 C9 . . . . -0.4(8) ?
    N2 C7 C8 C9 . . . . -179.7(5) ?
    C7 C8 C9 C10 . . . . 0.5(7) ?
    C8 C9 C10 C5 . . . . -0.4(7) ?
    C6 C5 C10 C9 . . . . 0.2(6) ?
    N1 C5 C10 C9 . . . . -179.1(4) ?
    C14 S4 C11 C12 . . . . 0.9(3) ?
    C14 S4 C11 S3 . . . . 174.4(2) ?
    O3 S3 C11 C12 . . . . -18.7(4) ?
    O4 S3 C11 C12 . . . . -153.7(3) ?
    N1 S3 C11 C12 . . . . 92.3(4) ?
    O3 S3 C11 S4 . . . . 168.6(2) ?
    O4 S3 C11 S4 . . . . 33.6(3) ?
    N1 S3 C11 S4 . . . . -80.4(2) ?
    S4 C11 C12 C13 . . . . -0.9(5) ?
    S3 C11 C12 C13 . . . . -174.2(3) ?
    C11 C12 C13 C14 . . . . 0.5(6) ?
    C12 C13 C14 S4 . . . . 0.2(5) ?
    C12 C13 C14 Br2 . . . . 177.6(3) ?
    C11 S4 C14 C13 . . . . -0.6(3) ?
    C11 S4 C14 Br2 . . . . -178.2(2) ?
data_global
_journal_date_recd_electronic     2007-04-30
_journal_date_accepted     2007-05-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      7
_journal_page_first     o3177
_journal_page_last     o3177
_journal_paper_category     QO
_journal_coeditor_code     CF2106
_publ_contact_author_name     'Jing Xiong'
_publ_contact_author_address
;
 School of Chemistry and Materials Engineering
 Wenzhou University
 Wenzhou, 325027
 P. R. China
;
_publ_contact_author_email     theresa_xiong@yahoo.com.cn
_publ_contact_author_fax     '86-577-88339081'
_publ_contact_author_phone     '86-577-88373111'
_publ_section_title
;
N,N-Bis(5-bromo-2-thienylsulfonyl)-3-nitroaniline
;
loop_
    _publ_author_name
    _publ_author_address
    'Shao-Miao Lin'
;
School of Chemistry and Materials Engineering
Wenzhou University
Wenzhou 325027
People's Republic of China
;
    'Mei Zheng'
;
School of Chemistry and Materials Engineering
Wenzhou University
Wenzhou 325027
People's Republic of China
;
    'Jing Xiong'
;
School of Chemistry and Materials Engineering
Wenzhou University
Wenzhou 325027
People's Republic of China
;
