##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-Bromo-2-formyl-6-methoxyphenyl benzenesulfonate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 Br O5 S'
_chemical_formula_sum     'C14 H11 Br O5 S'
_chemical_formula_iupac     'C14 H11 Br O5 S'
_chemical_formula_weight     371.20
_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     7.886(3)
_cell_length_b     22.445(9)
_cell_length_c     8.268(3)
_cell_angle_alpha     90.00
_cell_angle_beta     97.019(7)
_cell_angle_gamma     90.00
_cell_volume     1452.5(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3238
_cell_measurement_theta_min     2.64
_cell_measurement_theta_max     25.89
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.697
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     744
_exptl_absorpt_coefficient_mu     2.991
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.411
_exptl_absorpt_correction_T_max     0.584
_exptl_special_details     ?
_diffrn_ambient_temperature     294(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 SMART APEX CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_reflns_number     7939
_diffrn_reflns_av_R_equivalents     0.0206
_diffrn_reflns_av_sigmaI/netI     0.0255
_diffrn_reflns_theta_min     1.81
_diffrn_reflns_theta_max     26.14
_diffrn_reflns_theta_full     26.14
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -25
_diffrn_reflns_limit_k_max     27
_diffrn_reflns_limit_l_min     -5
_diffrn_reflns_limit_l_max     10
_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 > 2σ(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     2884
_reflns_number_gt     2190
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0518
_refine_ls_R_factor_gt     0.0335
_refine_ls_wR_factor_gt     0.0781
_refine_ls_wR_factor_ref     0.0863
_refine_ls_goodness_of_fit_ref     1.023
_refine_ls_restrained_S_all     1.023
_refine_ls_number_reflns     2884
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0413P)²+0.6897P] 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     0.443
_refine_diff_density_min     -0.459
_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'
    '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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1999)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     SHELXTL
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 0.43996(4) 0.322440(15) 0.45554(5) 0.07010(15) Uani d . 1 . .
    S S1 -0.15814(8) 0.09639(3) 0.21780(9) 0.04681(19) Uani d . 1 . .
    O O1 -0.3045(2) 0.06378(10) 0.2507(3) 0.0745(7) Uani d . 1 . .
    O O2 -0.1675(3) 0.13807(9) 0.0873(3) 0.0613(6) Uani d . 1 . .
    O O3 -0.1070(2) 0.13272(8) 0.3852(2) 0.0439(4) Uani d . 1 . .
    O O4 0.2113(2) 0.10490(8) 0.5095(3) 0.0553(5) Uani d . 1 . .
    O O5 -0.2319(3) 0.29583(10) 0.1881(3) 0.0660(6) Uani d . 1 . .
    C C1 0.0137(3) 0.04748(11) 0.2046(3) 0.0404(6) Uani d . 1 . .
    C C2 0.1426(3) 0.06506(13) 0.1165(4) 0.0502(7) Uani d . 1 . .
    H H2 0.1388 0.1022 0.0661 0.060 Uiso calc R 1 . .
    C C3 0.2774(4) 0.02682(17) 0.1043(4) 0.0647(9) Uani d . 1 . .
    H H3 0.3653 0.0381 0.0453 0.078 Uiso calc R 1 . .
    C C4 0.2820(4) -0.02733(16) 0.1782(4) 0.0671(10) Uani d . 1 . .
    H H4 0.3732 -0.0528 0.1685 0.081 Uiso calc R 1 . .
    C C5 0.1558(5) -0.04508(14) 0.2662(4) 0.0667(9) Uani d . 1 . .
    H H5 0.1616 -0.0823 0.3162 0.080 Uiso calc R 1 . .
    C C6 0.0182(4) -0.00750(13) 0.2814(4) 0.0548(7) Uani d . 1 . .
    H H6 -0.0686 -0.0190 0.3415 0.066 Uiso calc R 1 . .
    C C7 0.0194(3) 0.17732(11) 0.3914(3) 0.0393(6) Uani d . 1 . .
    C C8 -0.0224(3) 0.23472(12) 0.3379(3) 0.0403(6) Uani d . 1 . .
    C C9 0.1040(3) 0.27864(12) 0.3536(3) 0.0442(6) Uani d . 1 . .
    H H9 0.0792 0.3173 0.3177 0.053 Uiso calc R 1 . .
    C C10 0.2654(3) 0.26365(12) 0.4231(3) 0.0450(6) Uani d . 1 . .
    C C11 0.3091(3) 0.20642(12) 0.4751(3) 0.0469(7) Uani d . 1 . .
    H H11 0.4203 0.1977 0.5199 0.056 Uiso calc R 1 . .
    C C12 0.1850(3) 0.16222(12) 0.4597(3) 0.0432(6) Uani d . 1 . .
    C C13 -0.1989(3) 0.25149(13) 0.2669(4) 0.0489(7) Uani d . 1 . .
    H H13 -0.2882 0.2262 0.2845 0.059 Uiso calc R 1 . .
    C C14 0.3844(4) 0.08440(15) 0.5370(5) 0.0738(10) Uani d . 1 . .
    H H14A 0.4402 0.0925 0.4426 0.111 Uiso calc R 1 . .
    H H14B 0.3856 0.0423 0.5574 0.111 Uiso calc R 1 . .
    H H14C 0.4433 0.1047 0.6296 0.111 Uiso calc R 1 . .
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
    Br1 0.0490(2) 0.0571(2) 0.1037(3) -0.01632(14) 0.00738(18) -0.00635(18)
    S1 0.0306(3) 0.0472(4) 0.0610(4) 0.0022(3) -0.0009(3) -0.0086(3)
    O1 0.0354(11) 0.0773(15) 0.112(2) -0.0146(10) 0.0130(12) -0.0306(14)
    O2 0.0665(13) 0.0573(13) 0.0556(13) 0.0229(10) -0.0116(10) -0.0019(10)
    O3 0.0373(9) 0.0429(10) 0.0522(11) -0.0036(8) 0.0078(8) -0.0029(9)
    O4 0.0452(10) 0.0452(11) 0.0718(14) 0.0038(9) -0.0084(10) 0.0119(10)
    O5 0.0548(13) 0.0613(14) 0.0801(16) 0.0154(11) 0.0015(11) 0.0136(12)
    C1 0.0367(13) 0.0376(14) 0.0454(15) 0.0020(10) -0.0016(12) -0.0028(12)
    C2 0.0416(15) 0.0520(17) 0.0567(17) 0.0043(12) 0.0042(13) 0.0053(14)
    C3 0.0457(17) 0.085(2) 0.064(2) 0.0148(16) 0.0090(15) 0.0002(18)
    C4 0.064(2) 0.075(2) 0.058(2) 0.0330(18) -0.0090(17) -0.0104(18)
    C5 0.091(3) 0.0429(17) 0.061(2) 0.0166(17) -0.0135(19) 0.0037(15)
    C6 0.0639(18) 0.0437(16) 0.0563(18) -0.0038(14) 0.0054(15) 0.0036(14)
    C7 0.0359(13) 0.0416(14) 0.0408(14) -0.0015(11) 0.0069(11) -0.0031(11)
    C8 0.0376(13) 0.0430(15) 0.0413(14) 0.0038(11) 0.0084(11) -0.0037(12)
    C9 0.0450(15) 0.0394(14) 0.0492(16) 0.0006(11) 0.0095(12) 0.0004(12)
    C10 0.0404(14) 0.0453(15) 0.0507(16) -0.0076(12) 0.0106(12) -0.0072(13)
    C11 0.0338(13) 0.0523(17) 0.0533(17) -0.0004(12) -0.0001(12) -0.0023(14)
    C12 0.0405(14) 0.0449(15) 0.0439(15) 0.0020(11) 0.0044(12) 0.0008(12)
    C13 0.0399(14) 0.0474(16) 0.0594(18) 0.0072(12) 0.0061(13) -0.0057(14)
    C14 0.0563(18) 0.058(2) 0.100(3) 0.0145(16) -0.0210(19) 0.0007(19)
_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 C10 . 1.902(3) ?
    S1 O1 . 1.420(2) ?
    S1 O2 . 1.423(2) ?
    S1 O3 . 1.614(2) ?
    S1 C1 . 1.758(3) ?
    O3 C7 . 1.409(3) ?
    O4 C12 . 1.359(3) ?
    O4 C14 . 1.432(4) ?
    O5 C13 . 1.200(3) ?
    C1 C2 . 1.378(4) ?
    C1 C6 . 1.386(4) ?
    C2 C3 . 1.379(4) ?
    C2 H2 . 0.930 ?
    C3 C4 . 1.359(5) ?
    C3 H3 . 0.930 ?
    C4 C5 . 1.362(5) ?
    C4 H4 . 0.930 ?
    C5 C6 . 1.392(4) ?
    C5 H5 . 0.930 ?
    C6 H6 . 0.930 ?
    C7 C8 . 1.389(4) ?
    C7 C12 . 1.400(4) ?
    C8 C9 . 1.396(4) ?
    C8 C13 . 1.491(4) ?
    C9 C10 . 1.373(4) ?
    C9 H9 . 0.930 ?
    C10 C11 . 1.385(4) ?
    C11 C12 . 1.388(4) ?
    C11 H11 . 0.930 ?
    C13 H13 . 0.930 ?
    C14 H14A . 0.960 ?
    C14 H14B . 0.960 ?
    C14 H14C . 0.960 ?
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
    O1 S1 O2 . . 121.03(15) ?
    O1 S1 O3 . . 102.71(13) ?
    O2 S1 O3 . . 107.59(12) ?
    O1 S1 C1 . . 109.91(13) ?
    O2 S1 C1 . . 109.42(13) ?
    O3 S1 C1 . . 104.78(11) ?
    C7 O3 S1 . . 119.45(16) ?
    C12 O4 C14 . . 117.3(2) ?
    C2 C1 C6 . . 121.2(3) ?
    C2 C1 S1 . . 118.6(2) ?
    C6 C1 S1 . . 120.3(2) ?
    C1 C2 C3 . . 119.0(3) ?
    C1 C2 H2 . . 120.5 ?
    C3 C2 H2 . . 120.5 ?
    C4 C3 C2 . . 120.1(3) ?
    C4 C3 H3 . . 119.9 ?
    C2 C3 H3 . . 119.9 ?
    C3 C4 C5 . . 121.4(3) ?
    C3 C4 H4 . . 119.3 ?
    C5 C4 H4 . . 119.3 ?
    C4 C5 C6 . . 119.9(3) ?
    C4 C5 H5 . . 120.0 ?
    C6 C5 H5 . . 120.0 ?
    C1 C6 C5 . . 118.3(3) ?
    C1 C6 H6 . . 120.8 ?
    C5 C6 H6 . . 120.8 ?
    C8 C7 C12 . . 121.8(2) ?
    C8 C7 O3 . . 120.5(2) ?
    C12 C7 O3 . . 117.6(2) ?
    C7 C8 C9 . . 119.1(2) ?
    C7 C8 C13 . . 122.2(2) ?
    C9 C8 C13 . . 118.6(2) ?
    C10 C9 C8 . . 118.7(2) ?
    C10 C9 H9 . . 120.6 ?
    C8 C9 H9 . . 120.6 ?
    C9 C10 C11 . . 122.7(2) ?
    C9 C10 Br1 . . 120.5(2) ?
    C11 C10 Br1 . . 116.8(2) ?
    C10 C11 C12 . . 119.3(2) ?
    C10 C11 H11 . . 120.4 ?
    C12 C11 H11 . . 120.4 ?
    O4 C12 C11 . . 124.7(2) ?
    O4 C12 C7 . . 116.8(2) ?
    C11 C12 C7 . . 118.5(2) ?
    O5 C13 C8 . . 123.6(3) ?
    O5 C13 H13 . . 118.2 ?
    C8 C13 H13 . . 118.2 ?
    O4 C14 H14A . . 109.5 ?
    O4 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    O4 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
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
    O1 S1 O3 C7 . . . . -170.76(19) ?
    O2 S1 O3 C7 . . . . -42.0(2) ?
    C1 S1 O3 C7 . . . . 74.4(2) ?
    O1 S1 C1 C2 . . . . 156.0(2) ?
    O2 S1 C1 C2 . . . . 20.9(3) ?
    O3 S1 C1 C2 . . . . -94.3(2) ?
    O1 S1 C1 C6 . . . . -23.9(3) ?
    O2 S1 C1 C6 . . . . -159.1(2) ?
    O3 S1 C1 C6 . . . . 85.8(2) ?
    C6 C1 C2 C3 . . . . 0.5(4) ?
    S1 C1 C2 C3 . . . . -179.5(2) ?
    C1 C2 C3 C4 . . . . 0.0(5) ?
    C2 C3 C4 C5 . . . . -0.4(5) ?
    C3 C4 C5 C6 . . . . 0.2(5) ?
    C2 C1 C6 C5 . . . . -0.6(4) ?
    S1 C1 C6 C5 . . . . 179.3(2) ?
    C4 C5 C6 C1 . . . . 0.3(5) ?
    S1 O3 C7 C8 . . . . 84.0(3) ?
    S1 O3 C7 C12 . . . . -98.8(2) ?
    C12 C7 C8 C9 . . . . -0.4(4) ?
    O3 C7 C8 C9 . . . . 176.7(2) ?
    C12 C7 C8 C13 . . . . -179.2(3) ?
    O3 C7 C8 C13 . . . . -2.1(4) ?
    C7 C8 C9 C10 . . . . -0.6(4) ?
    C13 C8 C9 C10 . . . . 178.3(3) ?
    C8 C9 C10 C11 . . . . 1.4(4) ?
    C8 C9 C10 Br1 . . . . -177.4(2) ?
    C9 C10 C11 C12 . . . . -1.1(4) ?
    Br1 C10 C11 C12 . . . . 177.7(2) ?
    C14 O4 C12 C11 . . . . -18.2(4) ?
    C14 O4 C12 C7 . . . . 163.2(3) ?
    C10 C11 C12 O4 . . . . -178.5(3) ?
    C10 C11 C12 C7 . . . . 0.1(4) ?
    C8 C7 C12 O4 . . . . 179.3(2) ?
    O3 C7 C12 O4 . . . . 2.2(4) ?
    C8 C7 C12 C11 . . . . 0.7(4) ?
    O3 C7 C12 C11 . . . . -176.5(2) ?
    C7 C8 C13 O5 . . . . -163.1(3) ?
    C9 C8 C13 O5 . . . . 18.0(4) ?
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
    C6 H6 O4 3_556 0.93 2.62 3.436(4) 148 yes
data_global
_journal_date_recd_electronic     2006-12-13
_journal_date_accepted     2007-01-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      2
_journal_page_first     o646
_journal_page_last     o647
_journal_paper_category     EO
_journal_coeditor_code     BI2128
_publ_contact_author_name     'Chen, Xin'
_publ_contact_author_address
;
College of Sciences
Tianjin University of Science and Technology
Tianjin 300222
People's Republic of China
;
_publ_contact_author_email     chen_xin9999@163.com
_publ_contact_author_fax     '086(022)23001002'
_publ_contact_author_phone     '086(022)60270087'
_publ_section_title
;
4-Bromo-2-formyl-6-methoxyphenyl benzenesulfonate
;
loop_
    _publ_author_name
    _publ_author_address
    'Chen, Xin'
;
College of Sciences
Tianjin University of Science and Technology
Tianjin 300222
People's Republic of China
;
    'Yu, Ming'
;
College of Sciences
Tianjin University of Science and Technology
Tianjin 300222
People's Republic of China
;
