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###                                                                        ###
###        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.                                        #
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# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
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# 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  #
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data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
4-Methyl-2-oxo-2,3-dihydro-1-benzopyran-7-yl benzenesulfonate
;
_chemical_name_common
;
4-Methyl-7-phenylsulfonyloxy-2H-1-benzopyran-2-one
;
_chemical_formula_moiety     'C16 H12 O5 S'
_chemical_formula_sum     'C16 H12 O5 S'
_chemical_formula_iupac     'C16 H12 O5 S'
_chemical_formula_weight     316.32
_chemical_melting_point     493
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c n'
_symmetry_space_group_name_Hall     '-P 2n 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    '-x, y, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z-1/2'
    'x, -y, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     23.319(3)
_cell_length_b     9.0865(12)
_cell_length_c     13.7280(17)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2908.8(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     1900
_cell_measurement_theta_min     2.406
_cell_measurement_theta_max     22.801
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.23
_exptl_crystal_density_diffrn     1.445
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1312
_exptl_absorpt_coefficient_mu     0.244
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.8920
_exptl_absorpt_correction_T_max     0.9461
_exptl_special_details
;
;
_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     'Siemens SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11238
_diffrn_reflns_av_R_equivalents     0.0765
_diffrn_reflns_av_sigmaI/netI     0.0599
_diffrn_reflns_theta_min     1.75
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -27
_diffrn_reflns_limit_h_max     25
_diffrn_reflns_limit_k_min     -6
_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 >
σ(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     2557
_reflns_number_gt     1340
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1157
_refine_ls_R_factor_gt     0.0486
_refine_ls_wR_factor_gt     0.1145
_refine_ls_wR_factor_ref     0.1639
_refine_ls_goodness_of_fit_ref     1.086
_refine_ls_restrained_S_all     1.086
_refine_ls_number_reflns     2557
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w = 1/[σ²(Fo²)+(0.0635P)²+1.4P] 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     0.206
_refine_diff_density_min     -0.273
_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'
    'S' 'S' 0.1246 0.1234
                         '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'
_computing_data_collection     'SMART (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     'SAINT (Siemens, 1996)'
_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
    O O1 0.06623(10) 0.5712(3) 0.1179(2) 0.0475(7) Uani d . 1 . .
    O O2 0.01987(13) 0.7814(3) 0.1253(2) 0.0753(10) Uani d . 1 . .
    O O3 0.17597(10) 0.1409(3) 0.1092(2) 0.0554(8) Uani d . 1 . .
    O O4 0.25437(12) 0.0001(4) 0.0562(3) 0.0813(11) Uani d . 1 . .
    O O5 0.15694(13) -0.0921(3) 0.0244(2) 0.0686(9) Uani d . 1 . .
    S S1 0.19688(4) 0.02586(12) 0.02911(9) 0.0554(4) Uani d . 1 . .
    C C1 0.01573(17) 0.6497(5) 0.1241(3) 0.0511(11) Uani d . 1 . .
    C C2 -0.03663(17) 0.5658(5) 0.1266(3) 0.0518(11) Uani d . 1 . .
    H H2 -0.0712 0.6168 0.1297 0.062 Uiso calc R 1 . .
    C C3 -0.03837(15) 0.4190(4) 0.1249(3) 0.0443(10) Uani d . 1 . .
    C C4 0.01530(14) 0.3395(4) 0.1195(3) 0.0402(9) Uani d . 1 . .
    C C5 0.06587(16) 0.4202(4) 0.1156(3) 0.0397(9) Uani d . 1 . .
    C C6 0.11874(15) 0.3532(4) 0.1088(3) 0.0430(10) Uani d . 1 . .
    H H6 0.1521 0.4088 0.1047 0.052 Uiso calc R 1 . .
    C C7 0.12071(15) 0.2032(4) 0.1081(3) 0.0431(10) Uani d . 1 . .
    C C8 0.07195(17) 0.1177(4) 0.1123(3) 0.0529(11) Uani d . 1 . .
    H H8 0.0743 0.0155 0.1116 0.063 Uiso calc R 1 . .
    C C9 0.01984(17) 0.1871(4) 0.1176(3) 0.0514(11) Uani d . 1 . .
    H H9 -0.0134 0.1306 0.1199 0.062 Uiso calc R 1 . .
    C C10 -0.09430(15) 0.3386(5) 0.1251(3) 0.0669(13) Uani d . 1 . .
    H H10A -0.1251 0.4079 0.1317 0.100 Uiso calc R 1 . .
    H H10B -0.0951 0.2708 0.1787 0.100 Uiso calc R 1 . .
    H H10C -0.0985 0.2855 0.0651 0.100 Uiso calc R 1 . .
    C C11 0.19416(16) 0.1231(4) -0.0797(3) 0.0444(10) Uani d . 1 . .
    C C12 0.24038(18) 0.2080(5) -0.1072(4) 0.0699(14) Uani d . 1 . .
    H H12 0.2721 0.2163 -0.0665 0.084 Uiso calc R 1 . .
    C C13 0.2393(3) 0.2794(6) -0.1940(5) 0.0937(18) Uani d . 1 . .
    H H13 0.2705 0.3363 -0.2131 0.112 Uiso calc R 1 . .
    C C14 0.1923(3) 0.2683(6) -0.2538(4) 0.0906(18) Uani d . 1 . .
    H H14 0.1919 0.3175 -0.3132 0.109 Uiso calc R 1 . .
    C C15 0.1467(2) 0.1859(6) -0.2267(4) 0.0723(14) Uani d . 1 . .
    H H15 0.1149 0.1795 -0.2675 0.087 Uiso calc R 1 . .
    C C16 0.14680(18) 0.1116(5) -0.1394(3) 0.0583(12) Uani d . 1 . .
    H H16 0.1155 0.0547 -0.1209 0.070 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
    O1 0.0504(16) 0.0403(16) 0.0519(19) -0.0075(12) -0.0003(14) -0.0038(13)
    O2 0.089(2) 0.0449(19) 0.093(3) 0.0008(16) -0.0127(19) -0.0033(18)
    O3 0.0567(16) 0.0623(18) 0.0473(19) 0.0100(14) -0.0067(14) -0.0124(15)
    O4 0.0632(18) 0.099(3) 0.082(2) 0.0411(17) -0.0239(17) -0.0130(19)
    O5 0.084(2) 0.0457(17) 0.076(2) -0.0071(15) 0.0033(18) -0.0047(16)
    S1 0.0583(7) 0.0514(6) 0.0566(8) 0.0129(5) -0.0072(6) -0.0057(6)
    C1 0.063(3) 0.050(3) 0.041(3) -0.003(2) -0.005(2) -0.003(2)
    C2 0.050(2) 0.067(3) 0.039(3) 0.007(2) -0.003(2) -0.007(2)
    C3 0.045(2) 0.056(3) 0.032(2) -0.0075(19) 0.0005(18) -0.008(2)
    C4 0.045(2) 0.045(2) 0.030(2) -0.0130(18) 0.0001(18) -0.0077(18)
    C5 0.050(2) 0.037(2) 0.031(2) -0.0074(18) -0.0024(19) -0.0035(17)
    C6 0.045(2) 0.045(2) 0.039(2) -0.0116(18) 0.0002(18) -0.0040(19)
    C7 0.050(2) 0.045(2) 0.034(2) 0.0005(19) 0.0018(19) -0.0047(19)
    C8 0.065(3) 0.037(2) 0.057(3) -0.007(2) 0.003(2) -0.003(2)
    C9 0.053(3) 0.044(2) 0.057(3) -0.018(2) 0.003(2) -0.006(2)
    C10 0.047(2) 0.083(3) 0.071(4) -0.016(2) 0.003(2) -0.011(3)
    C11 0.043(2) 0.043(2) 0.047(3) 0.0069(19) -0.001(2) -0.009(2)
    C12 0.061(3) 0.083(3) 0.066(4) -0.014(3) 0.003(3) -0.018(3)
    C13 0.113(5) 0.099(4) 0.069(4) -0.029(4) 0.031(4) -0.004(4)
    C14 0.146(6) 0.071(4) 0.055(4) 0.016(4) 0.016(4) 0.002(3)
    C15 0.090(4) 0.073(3) 0.055(4) 0.022(3) -0.015(3) -0.007(3)
    C16 0.054(3) 0.058(3) 0.063(3) 0.003(2) -0.004(2) -0.005(2)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    O1 C5 . 1.373(4) ?
    O1 C1 . 1.379(4) ?
    O2 C1 . 1.201(4) ?
    O3 C7 . 1.407(4) ?
    O3 S1 . 1.594(3) ?
    O4 S1 . 1.411(3) ?
    O5 S1 . 1.421(3) ?
    S1 C11 . 1.736(4) ?
    C1 C2 . 1.440(5) ?
    C2 C3 . 1.334(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.447(5) ?
    C3 C10 . 1.495(5) ?
    C4 C9 . 1.389(5) ?
    C4 C5 . 1.390(4) ?
    C5 C6 . 1.378(5) ?
    C6 C7 . 1.364(5) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.378(5) ?
    C8 C9 . 1.371(5) ?
    C8 H8 . 0.9300 ?
    C9 H9 . 0.9300 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 C12 . 1.378(5) ?
    C11 C16 . 1.379(5) ?
    C12 C13 . 1.358(7) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.372(7) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.354(7) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.376(6) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
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
    C5 O1 C1 . . 120.9(3) ?
    C7 O3 S1 . . 122.4(2) ?
    O4 S1 O5 . . 120.6(2) ?
    O4 S1 O3 . . 102.59(17) ?
    O5 S1 O3 . . 109.02(17) ?
    O4 S1 C11 . . 110.2(2) ?
    O5 S1 C11 . . 108.70(19) ?
    O3 S1 C11 . . 104.37(16) ?
    O2 C1 O1 . . 116.6(4) ?
    O2 C1 C2 . . 126.5(4) ?
    O1 C1 C2 . . 116.9(3) ?
    C3 C2 C1 . . 123.7(4) ?
    C3 C2 H2 . . 118.2 ?
    C1 C2 H2 . . 118.2 ?
    C2 C3 C4 . . 118.3(3) ?
    C2 C3 C10 . . 121.0(4) ?
    C4 C3 C10 . . 120.7(4) ?
    C9 C4 C5 . . 117.4(3) ?
    C9 C4 C3 . . 124.4(3) ?
    C5 C4 C3 . . 118.2(3) ?
    O1 C5 C6 . . 115.9(3) ?
    O1 C5 C4 . . 122.1(3) ?
    C6 C5 C4 . . 121.9(3) ?
    C7 C6 C5 . . 118.2(3) ?
    C7 C6 H6 . . 120.9 ?
    C5 C6 H6 . . 120.9 ?
    C6 C7 C8 . . 122.4(3) ?
    C6 C7 O3 . . 115.6(3) ?
    C8 C7 O3 . . 121.9(3) ?
    C9 C8 C7 . . 118.3(4) ?
    C9 C8 H8 . . 120.8 ?
    C7 C8 H8 . . 120.8 ?
    C8 C9 C4 . . 121.8(3) ?
    C8 C9 H9 . . 119.1 ?
    C4 C9 H9 . . 119.1 ?
    C3 C10 H10A . . 109.5 ?
    C3 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C3 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C12 C11 C16 . . 120.4(4) ?
    C12 C11 S1 . . 119.5(3) ?
    C16 C11 S1 . . 120.1(3) ?
    C13 C12 C11 . . 119.5(5) ?
    C13 C12 H12 . . 120.2 ?
    C11 C12 H12 . . 120.2 ?
    C12 C13 C14 . . 120.4(5) ?
    C12 C13 H13 . . 119.8 ?
    C14 C13 H13 . . 119.8 ?
    C15 C14 C13 . . 120.3(5) ?
    C15 C14 H14 . . 119.9 ?
    C13 C14 H14 . . 119.9 ?
    C14 C15 C16 . . 120.5(5) ?
    C14 C15 H15 . . 119.7 ?
    C16 C15 H15 . . 119.7 ?
    C15 C16 C11 . . 118.9(4) ?
    C15 C16 H16 . . 120.6 ?
    C11 C16 H16 . . 120.6 ?
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
    C7 O3 S1 O4 . . . . 177.3(3) ?
    C7 O3 S1 O5 . . . . -53.7(3) ?
    C7 O3 S1 C11 . . . . 62.3(3) ?
    C5 O1 C1 O2 . . . . -179.7(4) ?
    C5 O1 C1 C2 . . . . -0.8(5) ?
    O2 C1 C2 C3 . . . . 179.8(4) ?
    O1 C1 C2 C3 . . . . 1.1(6) ?
    C1 C2 C3 C4 . . . . -0.4(6) ?
    C1 C2 C3 C10 . . . . -178.4(4) ?
    C2 C3 C4 C9 . . . . 179.7(4) ?
    C10 C3 C4 C9 . . . . -2.2(6) ?
    C2 C3 C4 C5 . . . . -0.6(5) ?
    C10 C3 C4 C5 . . . . 177.5(4) ?
    C1 O1 C5 C6 . . . . 179.6(3) ?
    C1 O1 C5 C4 . . . . -0.1(5) ?
    C9 C4 C5 O1 . . . . -179.5(3) ?
    C3 C4 C5 O1 . . . . 0.8(5) ?
    C9 C4 C5 C6 . . . . 0.8(6) ?
    C3 C4 C5 C6 . . . . -178.9(3) ?
    O1 C5 C6 C7 . . . . 178.8(3) ?
    C4 C5 C6 C7 . . . . -1.5(6) ?
    C5 C6 C7 C8 . . . . 1.1(6) ?
    C5 C6 C7 O3 . . . . -174.9(3) ?
    S1 O3 C7 C6 . . . . -125.2(3) ?
    S1 O3 C7 C8 . . . . 58.8(5) ?
    C6 C7 C8 C9 . . . . -0.1(6) ?
    O3 C7 C8 C9 . . . . 175.6(4) ?
    C7 C8 C9 C4 . . . . -0.6(6) ?
    C5 C4 C9 C8 . . . . 0.2(6) ?
    C3 C4 C9 C8 . . . . 179.9(4) ?
    O4 S1 C11 C12 . . . . -23.7(4) ?
    O5 S1 C11 C12 . . . . -157.9(3) ?
    O3 S1 C11 C12 . . . . 85.8(3) ?
    O4 S1 C11 C16 . . . . 154.3(3) ?
    O5 S1 C11 C16 . . . . 20.0(4) ?
    O3 S1 C11 C16 . . . . -96.2(3) ?
    C16 C11 C12 C13 . . . . -0.6(6) ?
    S1 C11 C12 C13 . . . . 177.4(4) ?
    C11 C12 C13 C14 . . . . 0.5(8) ?
    C12 C13 C14 C15 . . . . 0.0(8) ?
    C13 C14 C15 C16 . . . . -0.4(8) ?
    C14 C15 C16 C11 . . . . 0.3(7) ?
    C12 C11 C16 C15 . . . . 0.2(6) ?
    S1 C11 C16 C15 . . . . -177.8(3) ?
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
    C6 H6 O4 8_665 0.93 2.43 3.325(4) 162.7
    C8 H8 O2 1_545 0.93 2.48 3.293(5) 145.4
data_global
_journal_date_recd_electronic     2008-09-30
_journal_date_accepted     2008-10-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     11
_journal_page_first     o2088
_journal_page_last     o2088
_journal_paper_category     QO
_journal_coeditor_code     XU2456
_publ_contact_author_name     'Shu-Ping, Yang'
_publ_contact_author_address
;
School of Chemical Engineering
Huaihai Institute of Technology
Lianyungang 222005
People's Republic of China
;
_publ_contact_author_email     'yangshuping@hhit.edu.cn'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
4-Methyl-2-oxo-2,3-dihydro-1-benzopyran-7-yl benzenesulfonate
;
loop_
    _publ_author_name
    _publ_author_address
    'Shu-Ping Yang'
;
School of Chemical Engineering
Huaihai Institute of Technology
Lianyungang 222005
People's Republic of China
;
    'Da-Qi Wang'
;
College of Chemistry and Chemical Engineering
Liaocheng University
Shandong 252059
People's Republic of China
;
    'Li-Jun Han'
;
School of Mathematics and Science
Huaihai Institute of Technology
Lianyungang 222005
People's Republic of China
;
    'Yu-Fen Liu'
;
School of Chemical Engineering
Huaihai Institute of Technology
Lianyungang 222005
People's Republic of China
;
