##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-(4-Chlorophenylsulfonyl)-5-(4-fluorophenyl)-5-methylimidazolidine-2,4-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H12 Cl F N2 O4 S'
_chemical_formula_sum     'C16 H12 Cl F N2 O4 S'
_chemical_formula_iupac     'C16 H12 Cl F N2 O4 S'
_chemical_formula_weight     382.79
_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_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,-y,-z
_cell_length_a     9.6959(7)
_cell_length_b     10.0066(7)
_cell_length_c     16.6269(13)
_cell_angle_alpha     92.098(6)
_cell_angle_beta     93.630(6)
_cell_angle_gamma     103.056(6)
_cell_volume     1566.2(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     20500
_cell_measurement_theta_min     2.09
_cell_measurement_theta_max     29.49
_cell_measurement_temperature     173(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.623
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     784
_exptl_absorpt_coefficient_mu     0.414
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(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     'Stoe IPDS-2'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     30542
_diffrn_reflns_av_R_equivalents     0.0415
_diffrn_reflns_av_sigmaI/netI     0.0427
_diffrn_reflns_theta_min     2.09
_diffrn_reflns_theta_max     29.27
_diffrn_reflns_theta_full     29.27
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_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 >
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     8438
_reflns_number_gt     5836
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0586
_refine_ls_R_factor_gt     0.0373
_refine_ls_wR_factor_gt     0.0903
_refine_ls_wR_factor_ref     0.0953
_refine_ls_goodness_of_fit_ref     0.893
_refine_ls_restrained_S_all     0.893
_refine_ls_number_reflns     8438
_refine_ls_number_parameters     462
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0594P)²] 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     0.492
_refine_diff_density_min     -0.641
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0070(7)
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         '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     'X-AREA (Stoe & Cie, 2006)'
_computing_cell_refinement     'X-AREA (Stoe & Cie, 2006)'
_computing_data_reduction     'X-RED32 (Stoe & Cie, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'SHELXL97 (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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    Cl Cl1 0.91764(7) -0.33306(8) 0.44481(3) 0.0678(2) Uani . . 1.000
    S S1 1.07493(4) 0.03707(4) 0.15675(2) 0.02160(10)
                                                    Uani . . 1.000
    F F1 0.74943(12) 0.11810(12) 0.46455(6) 0.0435(4) Uani . . 1.000
    O O1 0.88878(13) -0.18444(11) 0.04068(7) 0.0292(3) Uani . . 1.000
    O O2 0.57120(12) 0.08199(11) 0.07970(6) 0.0266(3) Uani . . 1.000
    O O3 1.12161(12) 0.17630(11) 0.18656(8) 0.0317(3) Uani . . 1.000
    O O4 1.15471(12) -0.02016(12) 0.10155(7) 0.0306(3) Uani . . 1.000
    N N1 0.91377(13) 0.02536(12) 0.11173(7) 0.0188(3) Uani . . 1.000
    N N2 0.70525(14) -0.07265(13) 0.04699(7) 0.0217(4) Uani . . 1.000
    C C1 1.04515(16) -0.06802(16) 0.23943(9) 0.0239(4) Uani . . 1.000
    C C2 1.06304(19) -0.00804(19) 0.31679(10) 0.0324(5) Uani . . 1.000
    C C3 1.0280(2) -0.0905(2) 0.38108(10) 0.0412(6) Uani . . 1.000
    C C4 0.9731(2) -0.2300(2) 0.36571(11) 0.0399(6) Uani . . 1.000
    C C5 0.95939(19) -0.29070(19) 0.28916(11) 0.0350(5) Uani . . 1.000
    C C6 0.99744(17) -0.20954(16) 0.22461(10) 0.0271(5) Uani . . 1.000
    C C7 0.84130(17) -0.08949(14) 0.06303(8) 0.0211(4) Uani . . 1.000
    C C8 0.68087(16) 0.04368(14) 0.08337(8) 0.0192(4) Uani . . 1.000
    C C9 0.81941(15) 0.11962(13) 0.13079(8) 0.0175(4) Uani . . 1.000
    C C10 0.86819(16) 0.25816(14) 0.09386(9) 0.0227(4) Uani . . 1.000
    C C11 0.79666(15) 0.12483(14) 0.22069(8) 0.0180(4) Uani . . 1.000
    C C12 0.84186(16) 0.24448(15) 0.26969(9) 0.0230(4) Uani . . 1.000
    C C13 0.82563(18) 0.24327(17) 0.35230(9) 0.0287(5) Uani . . 1.000
    C C14 0.76299(18) 0.12121(18) 0.38395(9) 0.0282(5) Uani . . 1.000
    C C15 0.71357(17) 0.00078(16) 0.33735(9) 0.0264(4) Uani . . 1.000
    C C16 0.73163(16) 0.00364(15) 0.25529(8) 0.0221(4) Uani . . 1.000
    Cl Cl2 0.40511(6) 0.12790(6) 0.43991(3) 0.0533(2) Uani . . 1.000
    S S2 0.58277(4) 0.54282(4) 0.17383(2) 0.02380(10)
                                                    Uani . . 1.000
    F F2 0.23250(13) 0.58675(13) 0.47233(6) 0.0462(4) Uani . . 1.000
    O O5 0.41852(14) 0.33765(12) 0.04019(7) 0.0323(4) Uani . . 1.000
    O O6 0.08075(12) 0.57818(11) 0.08571(6) 0.0268(3) Uani . . 1.000
    O O7 0.62142(12) 0.67806(11) 0.21087(8) 0.0329(4) Uani . . 1.000
    O O8 0.67356(13) 0.49688(12) 0.12089(8) 0.0349(4) Uani . . 1.000
    N N3 0.42774(14) 0.53320(12) 0.12274(7) 0.0207(4) Uani . . 1.000
    N N4 0.22860(15) 0.43999(13) 0.04734(7) 0.0245(4) Uani . . 1.000
    C C17 0.54287(17) 0.42502(15) 0.25006(9) 0.0246(4) Uani . . 1.000
    C C18 0.55335(19) 0.47308(18) 0.32980(10) 0.0314(5) Uani . . 1.000
    C C19 0.5129(2) 0.3808(2) 0.38883(10) 0.0366(6) Uani . . 1.000
    C C20 0.46166(19) 0.24306(19) 0.36642(10) 0.0340(5) Uani . . 1.000
    C C21 0.45376(18) 0.19449(17) 0.28735(10) 0.0313(5) Uani . . 1.000
    C C22 0.49622(17) 0.28577(15) 0.22782(9) 0.0258(4) Uani . . 1.000
    C C23 0.36440(17) 0.42562(15) 0.06618(8) 0.0234(4) Uani . . 1.000
    C C24 0.19359(16) 0.54614(14) 0.08942(8) 0.0203(4) Uani . . 1.000
    C C25 0.32640(15) 0.62082(13) 0.14231(8) 0.0181(4) Uani . . 1.000
    C C26 0.37432(17) 0.76406(14) 0.11053(9) 0.0235(4) Uani . . 1.000
    C C27 0.29616(15) 0.61719(14) 0.23119(8) 0.0188(4) Uani . . 1.000
    C C28 0.34294(17) 0.73075(15) 0.28478(9) 0.0250(4) Uani . . 1.000
    C C29 0.32074(18) 0.72166(17) 0.36611(10) 0.0312(5) Uani . . 1.000
    C C30 0.25095(18) 0.59752(18) 0.39255(9) 0.0300(5) Uani . . 1.000
    C C31 0.19982(18) 0.48331(17) 0.34161(9) 0.0280(5) Uani . . 1.000
    C C32 0.22340(16) 0.49359(15) 0.26027(9) 0.0226(4) Uani . . 1.000
    H H2 1.09880 0.08820 0.32580 0.0390 Uiso calc R 1.000
    H H2N 0.646(2) -0.124(2) 0.0142(12) 0.037(5) Uiso . . 1.000
    H H3 1.04140 -0.05190 0.43480 0.0490 Uiso calc R 1.000
    H H5 0.92420 -0.38710 0.28060 0.0420 Uiso calc R 1.000
    H H6 0.99110 -0.24960 0.17140 0.0330 Uiso calc R 1.000
    H H10A 0.88320 0.24360 0.03680 0.0340 Uiso calc R 1.000
    H H10B 0.95730 0.30860 0.12250 0.0340 Uiso calc R 1.000
    H H10C 0.79550 0.31140 0.09860 0.0340 Uiso calc R 1.000
    H H12 0.88430 0.32790 0.24650 0.0280 Uiso calc R 1.000
    H H13 0.85700 0.32470 0.38590 0.0340 Uiso calc R 1.000
    H H15 0.66860 -0.08150 0.36080 0.0320 Uiso calc R 1.000
    H H16 0.69920 -0.07820 0.22210 0.0260 Uiso calc R 1.000
    H H4N 0.170(2) 0.3855(19) 0.0117(11) 0.031(5) Uiso . . 1.000
    H H18 0.58780 0.56820 0.34390 0.0380 Uiso calc R 1.000
    H H19 0.52030 0.41170 0.44400 0.0440 Uiso calc R 1.000
    H H21 0.41950 0.09920 0.27360 0.0370 Uiso calc R 1.000
    H H22 0.49350 0.25380 0.17310 0.0310 Uiso calc R 1.000
    H H26A 0.38990 0.75590 0.05310 0.0350 Uiso calc R 1.000
    H H26B 0.46290 0.81250 0.14050 0.0350 Uiso calc R 1.000
    H H26C 0.30080 0.81560 0.11770 0.0350 Uiso calc R 1.000
    H H28 0.39080 0.81570 0.26540 0.0300 Uiso calc R 1.000
    H H29 0.35290 0.79930 0.40270 0.0370 Uiso calc R 1.000
    H H31 0.14980 0.39970 0.36150 0.0340 Uiso calc R 1.000
    H H32 0.18970 0.41570 0.22400 0.0270 Uiso calc R 1.000
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
    Cl1 0.0535(3) 0.1057(5) 0.0463(3) 0.0147(3) 0.0103(2) 0.0444(3)
    S1 0.0190(2) 0.0171(2) 0.0295(2) 0.00540(10)
                                               0.00280(10)
                                                         0.00190(10)
    F1 0.0520(7) 0.0584(7) 0.0186(4) 0.0092(6) 0.0052(4) -0.0020(4)
    O1 0.0364(7) 0.0210(5) 0.0314(6) 0.0107(5) 0.0030(5) -0.0080(4)
    O2 0.0221(6) 0.0302(6) 0.0276(5) 0.0082(5) -0.0011(4) -0.0042(4)
    O3 0.0229(6) 0.0182(5) 0.0510(7) 0.0013(4) -0.0054(5) -0.0014(5)
    O4 0.0285(6) 0.0317(6) 0.0378(6) 0.0155(5) 0.0141(5) 0.0092(5)
    N1 0.0203(6) 0.0147(5) 0.0224(6) 0.0064(5) 0.0025(5) -0.0006(4)
    N2 0.0227(7) 0.0201(6) 0.0204(6) 0.0017(5) 0.0021(5) -0.0065(5)
    C1 0.0226(8) 0.0254(8) 0.0254(7) 0.0096(6) 0.0004(6) 0.0015(6)
    C2 0.0339(9) 0.0370(9) 0.0283(8) 0.0156(7) -0.0056(7) -0.0050(7)
    C3 0.0420(11) 0.0633(13) 0.0245(8) 0.0260(10) 0.0002(7) 0.0011(8)
    C4 0.0297(9) 0.0606(13) 0.0338(9) 0.0160(9) 0.0046(7) 0.0213(8)
    C5 0.0292(9) 0.0355(9) 0.0400(9) 0.0057(7) -0.0013(7) 0.0139(7)
    C6 0.0277(8) 0.0244(8) 0.0290(8) 0.0057(6) -0.0006(6) 0.0042(6)
    C7 0.0283(8) 0.0156(6) 0.0192(6) 0.0045(6) 0.0047(5) -0.0015(5)
    C8 0.0220(7) 0.0182(6) 0.0164(6) 0.0021(5) 0.0027(5) 0.0005(5)
    C9 0.0191(7) 0.0127(6) 0.0214(6) 0.0048(5) 0.0029(5) -0.0004(5)
    C10 0.0249(8) 0.0166(7) 0.0279(7) 0.0057(6) 0.0049(6) 0.0057(5)
    C11 0.0185(7) 0.0152(6) 0.0200(6) 0.0038(5) 0.0013(5) -0.0012(5)
    C12 0.0232(8) 0.0177(7) 0.0263(7) 0.0016(6) 0.0030(6) -0.0031(5)
    C13 0.0297(9) 0.0279(8) 0.0269(7) 0.0054(7) 0.0000(6) -0.0102(6)
    C14 0.0285(8) 0.0390(9) 0.0179(7) 0.0097(7) 0.0028(6) -0.0012(6)
    C15 0.0287(8) 0.0264(8) 0.0242(7) 0.0054(6) 0.0041(6) 0.0048(6)
    C16 0.0249(8) 0.0180(7) 0.0223(7) 0.0029(6) 0.0018(6) 0.0005(5)
    Cl2 0.0499(3) 0.0667(4) 0.0426(3) 0.0081(3) 0.0044(2) 0.0272(2)
    S2 0.0205(2) 0.0163(2) 0.0358(2) 0.00560(10)
                                               0.0049(2) 0.00180(10)
    F2 0.0560(7) 0.0628(7) 0.0196(5) 0.0125(6) 0.0054(5) 0.0011(4)
    O5 0.0425(7) 0.0245(6) 0.0328(6) 0.0144(5) 0.0061(5) -0.0079(4)
    O6 0.0237(6) 0.0278(6) 0.0280(5) 0.0056(5) 0.0004(4) -0.0041(4)
    O7 0.0245(6) 0.0162(5) 0.0560(8) 0.0032(4) -0.0033(5) -0.0025(5)
    O8 0.0296(6) 0.0311(6) 0.0500(7) 0.0148(5) 0.0166(5) 0.0097(5)
    N3 0.0250(7) 0.0154(6) 0.0231(6) 0.0069(5) 0.0047(5) -0.0009(4)
    N4 0.0304(7) 0.0214(6) 0.0206(6) 0.0045(5) 0.0023(5) -0.0065(5)
    C17 0.0227(8) 0.0210(7) 0.0316(8) 0.0090(6) -0.0001(6) 0.0003(6)
    C18 0.0339(9) 0.0307(9) 0.0316(8) 0.0146(7) -0.0055(7) -0.0052(6)
    C19 0.0395(10) 0.0476(11) 0.0269(8) 0.0208(8) -0.0030(7) -0.0006(7)
    C20 0.0297(9) 0.0434(10) 0.0318(8) 0.0131(8) 0.0017(7) 0.0126(7)
    C21 0.0288(9) 0.0251(8) 0.0383(9) 0.0037(7) -0.0029(7) 0.0061(7)
    C22 0.0290(8) 0.0207(7) 0.0277(7) 0.0066(6) -0.0004(6) 0.0007(6)
    C23 0.0304(8) 0.0185(7) 0.0218(7) 0.0058(6) 0.0054(6) -0.0002(5)
    C24 0.0253(8) 0.0166(6) 0.0183(6) 0.0024(6) 0.0042(5) 0.0014(5)
    C25 0.0196(7) 0.0128(6) 0.0226(6) 0.0045(5) 0.0040(5) 0.0005(5)
    C26 0.0241(8) 0.0142(6) 0.0326(8) 0.0040(6) 0.0053(6) 0.0048(5)
    C27 0.0196(7) 0.0157(6) 0.0207(6) 0.0037(5) 0.0015(5) -0.0016(5)
    C28 0.0261(8) 0.0176(7) 0.0296(7) 0.0022(6) 0.0030(6) -0.0053(5)
    C29 0.0330(9) 0.0314(8) 0.0273(8) 0.0061(7) -0.0001(7) -0.0116(6)
    C30 0.0314(9) 0.0418(10) 0.0180(7) 0.0108(7) 0.0026(6) -0.0008(6)
    C31 0.0297(9) 0.0276(8) 0.0259(7) 0.0036(7) 0.0035(6) 0.0055(6)
    C32 0.0247(8) 0.0181(7) 0.0231(7) 0.0017(6) 0.0009(6) -0.0004(5)
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C4 . . 1.738(2) no
    Cl2 C20 . . 1.7390(18) no
    S1 O4 . . 1.4214(12) no
    S1 N1 . . 1.6669(13) no
    S1 C1 . . 1.7601(16) no
    S1 O3 . . 1.4240(12) no
    S2 O7 . . 1.4254(12) no
    S2 O8 . . 1.4186(14) no
    S2 C17 . . 1.7638(15) no
    S2 N3 . . 1.6605(14) no
    F1 C14 . . 1.3556(18) no
    F2 C30 . . 1.3546(18) no
    O1 C7 . . 1.2026(19) no
    O2 C8 . . 1.208(2) no
    O5 C23 . . 1.203(2) no
    O6 C24 . . 1.206(2) no
    N1 C7 . . 1.4018(18) no
    N1 C9 . . 1.4939(19) no
    N2 C7 . . 1.378(2) no
    N2 C8 . . 1.3666(19) no
    N2 H2N . . 0.84(2) no
    N3 C23 . . 1.4052(18) no
    N3 C25 . . 1.4996(19) no
    N4 C23 . . 1.375(2) no
    N4 C24 . . 1.3681(19) no
    N4 H4N . . 0.875(19) no
    C1 C6 . . 1.394(2) no
    C1 C2 . . 1.383(2) no
    C2 C3 . . 1.387(2) no
    C3 C4 . . 1.385(3) no
    C4 C5 . . 1.376(3) no
    C5 C6 . . 1.388(2) no
    C8 C9 . . 1.538(2) no
    C9 C10 . . 1.5250(19) no
    C9 C11 . . 1.5254(19) no
    C11 C16 . . 1.397(2) no
    C11 C12 . . 1.391(2) no
    C12 C13 . . 1.393(2) no
    C13 C14 . . 1.375(2) no
    C14 C15 . . 1.381(2) no
    C15 C16 . . 1.387(2) no
    C2 H2 . . 0.9500 no
    C3 H3 . . 0.9500 no
    C5 H5 . . 0.9500 no
    C6 H6 . . 0.9500 no
    C10 H10A . . 0.9800 no
    C10 H10B . . 0.9800 no
    C10 H10C . . 0.9800 no
    C12 H12 . . 0.9500 no
    C13 H13 . . 0.9500 no
    C15 H15 . . 0.9500 no
    C16 H16 . . 0.9500 no
    C17 C22 . . 1.393(2) no
    C17 C18 . . 1.383(2) no
    C18 C19 . . 1.386(2) no
    C19 C20 . . 1.384(3) no
    C20 C21 . . 1.376(2) no
    C21 C22 . . 1.390(2) no
    C24 C25 . . 1.537(2) no
    C25 C26 . . 1.5281(19) no
    C25 C27 . . 1.5249(19) no
    C27 C32 . . 1.398(2) no
    C27 C28 . . 1.390(2) no
    C28 C29 . . 1.386(2) no
    C29 C30 . . 1.376(2) no
    C30 C31 . . 1.375(2) no
    C31 C32 . . 1.390(2) no
    C18 H18 . . 0.9500 no
    C19 H19 . . 0.9500 no
    C21 H21 . . 0.9500 no
    C22 H22 . . 0.9500 no
    C26 H26A . . 0.9800 no
    C26 H26B . . 0.9800 no
    C26 H26C . . 0.9800 no
    C28 H28 . . 0.9500 no
    C29 H29 . . 0.9500 no
    C31 H31 . . 0.9500 no
    C32 H32 . . 0.9500 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O3 S1 O4 . . . 120.54(7) no
    O3 S1 N1 . . . 105.32(7) no
    O3 S1 C1 . . . 108.55(8) no
    O4 S1 N1 . . . 107.44(7) no
    O4 S1 C1 . . . 109.31(7) no
    N1 S1 C1 . . . 104.49(7) no
    O8 S2 N3 . . . 107.85(7) no
    O8 S2 C17 . . . 109.35(8) no
    N3 S2 C17 . . . 104.29(7) no
    O7 S2 C17 . . . 108.38(7) no
    O7 S2 O8 . . . 120.43(7) no
    O7 S2 N3 . . . 105.34(7) no
    C7 N1 C9 . . . 111.78(12) no
    S1 N1 C9 . . . 124.37(9) no
    S1 N1 C7 . . . 122.81(11) no
    C7 N2 C8 . . . 113.69(12) no
    C8 N2 H2N . . . 122.9(14) no
    C7 N2 H2N . . . 123.1(14) no
    S2 N3 C25 . . . 124.18(9) no
    S2 N3 C23 . . . 123.49(11) no
    C23 N3 C25 . . . 111.33(12) no
    C23 N4 C24 . . . 114.09(12) no
    C24 N4 H4N . . . 123.3(13) no
    C23 N4 H4N . . . 122.6(13) no
    S1 C1 C6 . . . 118.72(12) no
    C2 C1 C6 . . . 121.81(15) no
    S1 C1 C2 . . . 119.40(13) no
    C1 C2 C3 . . . 119.02(17) no
    C2 C3 C4 . . . 118.98(16) no
    Cl1 C4 C3 . . . 119.61(14) no
    Cl1 C4 C5 . . . 118.26(15) no
    C3 C4 C5 . . . 122.13(17) no
    C4 C5 C6 . . . 119.27(17) no
    C1 C6 C5 . . . 118.64(15) no
    O1 C7 N1 . . . 126.44(15) no
    N1 C7 N2 . . . 106.47(12) no
    O1 C7 N2 . . . 127.08(14) no
    N2 C8 C9 . . . 107.77(13) no
    O2 C8 C9 . . . 125.18(13) no
    O2 C8 N2 . . . 127.05(14) no
    C10 C9 C11 . . . 115.85(11) no
    N1 C9 C8 . . . 100.25(10) no
    N1 C9 C10 . . . 111.26(12) no
    C8 C9 C10 . . . 107.59(11) no
    C8 C9 C11 . . . 109.55(12) no
    N1 C9 C11 . . . 111.12(11) no
    C12 C11 C16 . . . 118.98(13) no
    C9 C11 C16 . . . 118.47(12) no
    C9 C11 C12 . . . 122.52(12) no
    C11 C12 C13 . . . 120.71(14) no
    C12 C13 C14 . . . 118.31(14) no
    F1 C14 C15 . . . 118.21(15) no
    C13 C14 C15 . . . 122.95(14) no
    F1 C14 C13 . . . 118.84(15) no
    C14 C15 C16 . . . 117.94(14) no
    C11 C16 C15 . . . 121.08(13) no
    C3 C2 H2 . . . 120.00 no
    C1 C2 H2 . . . 121.00 no
    C2 C3 H3 . . . 120.00 no
    C4 C3 H3 . . . 121.00 no
    C4 C5 H5 . . . 120.00 no
    C6 C5 H5 . . . 120.00 no
    C1 C6 H6 . . . 121.00 no
    C5 C6 H6 . . . 121.00 no
    C9 C10 H10B . . . 109.00 no
    H10A C10 H10C . . . 109.00 no
    H10B C10 H10C . . . 109.00 no
    C9 C10 H10A . . . 109.00 no
    C9 C10 H10C . . . 109.00 no
    H10A C10 H10B . . . 109.00 no
    C13 C12 H12 . . . 120.00 no
    C11 C12 H12 . . . 120.00 no
    C14 C13 H13 . . . 121.00 no
    C12 C13 H13 . . . 121.00 no
    C16 C15 H15 . . . 121.00 no
    C14 C15 H15 . . . 121.00 no
    C15 C16 H16 . . . 119.00 no
    C11 C16 H16 . . . 119.00 no
    S2 C17 C18 . . . 119.53(12) no
    C18 C17 C22 . . . 121.65(14) no
    S2 C17 C22 . . . 118.78(11) no
    C17 C18 C19 . . . 119.20(16) no
    C18 C19 C20 . . . 119.16(16) no
    Cl2 C20 C21 . . . 118.94(14) no
    Cl2 C20 C19 . . . 119.28(13) no
    C19 C20 C21 . . . 121.79(16) no
    C20 C21 C22 . . . 119.53(15) no
    C17 C22 C21 . . . 118.62(14) no
    N3 C23 N4 . . . 106.55(13) no
    O5 C23 N3 . . . 126.46(15) no
    O5 C23 N4 . . . 126.98(14) no
    O6 C24 N4 . . . 127.18(14) no
    O6 C24 C25 . . . 125.42(13) no
    N4 C24 C25 . . . 107.39(13) no
    N3 C25 C24 . . . 100.55(10) no
    C24 C25 C26 . . . 107.20(11) no
    C24 C25 C27 . . . 110.25(12) no
    C26 C25 C27 . . . 115.47(11) no
    N3 C25 C26 . . . 110.75(12) no
    N3 C25 C27 . . . 111.50(11) no
    C28 C27 C32 . . . 118.95(13) no
    C25 C27 C28 . . . 122.38(12) no
    C25 C27 C32 . . . 118.63(12) no
    C27 C28 C29 . . . 120.87(14) no
    C28 C29 C30 . . . 118.37(15) no
    F2 C30 C31 . . . 118.41(15) no
    F2 C30 C29 . . . 118.72(15) no
    C29 C30 C31 . . . 122.88(15) no
    C30 C31 C32 . . . 118.17(15) no
    C27 C32 C31 . . . 120.74(14) no
    C17 C18 H18 . . . 120.00 no
    C19 C18 H18 . . . 120.00 no
    C18 C19 H19 . . . 120.00 no
    C20 C19 H19 . . . 120.00 no
    C20 C21 H21 . . . 120.00 no
    C22 C21 H21 . . . 120.00 no
    C17 C22 H22 . . . 121.00 no
    C21 C22 H22 . . . 121.00 no
    C25 C26 H26A . . . 109.00 no
    C25 C26 H26B . . . 109.00 no
    C25 C26 H26C . . . 109.00 no
    H26A C26 H26B . . . 110.00 no
    H26A C26 H26C . . . 109.00 no
    H26B C26 H26C . . . 109.00 no
    C27 C28 H28 . . . 120.00 no
    C29 C28 H28 . . . 120.00 no
    C28 C29 H29 . . . 121.00 no
    C30 C29 H29 . . . 121.00 no
    C30 C31 H31 . . . 121.00 no
    C32 C31 H31 . . . 121.00 no
    C27 C32 H32 . . . 120.00 no
    C31 C32 H32 . . . 120.00 no
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
    O3 S1 N1 C7 . . . . 169.06(11) no
    O3 S1 N1 C9 . . . . -23.58(13) no
    O4 S1 N1 C7 . . . . 39.41(13) no
    O4 S1 N1 C9 . . . . -153.24(11) no
    C1 S1 N1 C7 . . . . -76.64(12) no
    C1 S1 N1 C9 . . . . 90.72(12) no
    O3 S1 C1 C2 . . . . 2.56(16) no
    O3 S1 C1 C6 . . . . 179.52(13) no
    O4 S1 C1 C2 . . . . 135.82(14) no
    O4 S1 C1 C6 . . . . -47.21(15) no
    N1 S1 C1 C2 . . . . -109.44(14) no
    N1 S1 C1 C6 . . . . 67.53(14) no
    O7 S2 N3 C23 . . . . 168.37(12) no
    O7 S2 N3 C25 . . . . -24.06(13) no
    O8 S2 N3 C23 . . . . 38.58(13) no
    O8 S2 N3 C25 . . . . -153.85(11) no
    C17 S2 N3 C23 . . . . -77.60(13) no
    C17 S2 N3 C25 . . . . 89.98(12) no
    O7 S2 C17 C18 . . . . -0.26(17) no
    O7 S2 C17 C22 . . . . 177.31(13) no
    O8 S2 C17 C18 . . . . 132.76(15) no
    O8 S2 C17 C22 . . . . -49.67(16) no
    N3 S2 C17 C18 . . . . -112.11(15) no
    N3 S2 C17 C22 . . . . 65.46(15) no
    S1 N1 C9 C8 . . . . -170.14(9) no
    S1 N1 C9 C10 . . . . 76.29(14) no
    S1 N1 C9 C11 . . . . -54.40(15) no
    S1 N1 C7 O1 . . . . -8.4(2) no
    S1 N1 C7 N2 . . . . 170.79(9) no
    C9 N1 C7 O1 . . . . -177.21(14) no
    C9 N1 C7 N2 . . . . 2.00(15) no
    C7 N1 C9 C8 . . . . -1.56(14) no
    C7 N1 C9 C10 . . . . -115.13(13) no
    C7 N1 C9 C11 . . . . 114.18(13) no
    C7 N2 C8 O2 . . . . -179.43(14) no
    C7 N2 C8 C9 . . . . 0.64(16) no
    C8 N2 C7 O1 . . . . 177.57(14) no
    C8 N2 C7 N1 . . . . -1.63(16) no
    C25 N3 C23 O5 . . . . -178.52(14) no
    S2 N3 C23 O5 . . . . -9.5(2) no
    S2 N3 C23 N4 . . . . 169.79(10) no
    C23 N3 C25 C27 . . . . 117.74(12) no
    C25 N3 C23 N4 . . . . 0.80(15) no
    S2 N3 C25 C24 . . . . -168.02(9) no
    S2 N3 C25 C26 . . . . 78.89(14) no
    S2 N3 C25 C27 . . . . -51.16(15) no
    C23 N3 C25 C24 . . . . 0.88(14) no
    C23 N3 C25 C26 . . . . -112.22(13) no
    C23 N4 C24 O6 . . . . -177.93(14) no
    C24 N4 C23 O5 . . . . 176.83(14) no
    C24 N4 C23 N3 . . . . -2.48(16) no
    C23 N4 C24 C25 . . . . 3.07(16) no
    S1 C1 C2 C3 . . . . 174.66(14) no
    C2 C1 C6 C5 . . . . 3.8(3) no
    C6 C1 C2 C3 . . . . -2.2(3) no
    S1 C1 C6 C5 . . . . -173.13(13) no
    C1 C2 C3 C4 . . . . -1.5(3) no
    C2 C3 C4 Cl1 . . . . -175.76(15) no
    C2 C3 C4 C5 . . . . 3.6(3) no
    Cl1 C4 C5 C6 . . . . 177.33(14) no
    C3 C4 C5 C6 . . . . -2.1(3) no
    C4 C5 C6 C1 . . . . -1.6(3) no
    O2 C8 C9 C11 . . . . 63.69(17) no
    O2 C8 C9 C10 . . . . -63.03(18) no
    N2 C8 C9 C11 . . . . -116.37(12) no
    N2 C8 C9 N1 . . . . 0.56(13) no
    N2 C8 C9 C10 . . . . 116.91(12) no
    O2 C8 C9 N1 . . . . -179.38(13) no
    C8 C9 C11 C12 . . . . -133.46(14) no
    C8 C9 C11 C16 . . . . 48.46(17) no
    C10 C9 C11 C12 . . . . -11.6(2) no
    C10 C9 C11 C16 . . . . 170.35(14) no
    N1 C9 C11 C12 . . . . 116.69(15) no
    N1 C9 C11 C16 . . . . -61.39(17) no
    C9 C11 C12 C13 . . . . -176.64(15) no
    C12 C11 C16 C15 . . . . -0.9(2) no
    C16 C11 C12 C13 . . . . 1.4(2) no
    C9 C11 C16 C15 . . . . 177.24(14) no
    C11 C12 C13 C14 . . . . -0.5(2) no
    C12 C13 C14 C15 . . . . -1.1(3) no
    C12 C13 C14 F1 . . . . 178.57(15) no
    C13 C14 C15 C16 . . . . 1.6(3) no
    F1 C14 C15 C16 . . . . -178.08(15) no
    C14 C15 C16 C11 . . . . -0.6(2) no
    S2 C17 C18 C19 . . . . 175.79(15) no
    C22 C17 C18 C19 . . . . -1.7(3) no
    S2 C17 C22 C21 . . . . -174.77(13) no
    C18 C17 C22 C21 . . . . 2.8(3) no
    C17 C18 C19 C20 . . . . -0.7(3) no
    C18 C19 C20 Cl2 . . . . -177.81(15) no
    C18 C19 C20 C21 . . . . 2.0(3) no
    Cl2 C20 C21 C22 . . . . 178.86(14) no
    C19 C20 C21 C22 . . . . -1.0(3) no
    C20 C21 C22 C17 . . . . -1.4(3) no
    O6 C24 C25 N3 . . . . 178.72(13) no
    O6 C24 C25 C26 . . . . -65.50(18) no
    O6 C24 C25 C27 . . . . 60.94(18) no
    N4 C24 C25 N3 . . . . -2.26(13) no
    N4 C24 C25 C26 . . . . 113.52(13) no
    N4 C24 C25 C27 . . . . -120.04(12) no
    N3 C25 C27 C28 . . . . 111.40(15) no
    N3 C25 C27 C32 . . . . -66.12(17) no
    C24 C25 C27 C28 . . . . -137.80(14) no
    C24 C25 C27 C32 . . . . 44.67(18) no
    C26 C25 C27 C28 . . . . -16.1(2) no
    C26 C25 C27 C32 . . . . 166.34(14) no
    C25 C27 C28 C29 . . . . -176.22(15) no
    C32 C27 C28 C29 . . . . 1.3(2) no
    C25 C27 C32 C31 . . . . 176.65(15) no
    C28 C27 C32 C31 . . . . -1.0(2) no
    C27 C28 C29 C30 . . . . -0.1(3) no
    C28 C29 C30 F2 . . . . 178.10(16) no
    C28 C29 C30 C31 . . . . -1.4(3) no
    F2 C30 C31 C32 . . . . -177.78(15) no
    C29 C30 C31 C32 . . . . 1.8(3) no
    C30 C31 C32 C27 . . . . -0.5(2) no
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
    N2 H2N O5 2_655 0.84(2) 2.23(2) 2.9383(17) 143.0(18) yes
    N4 H4N O1 2_655 0.875(19) 2.103(19) 2.8595(17) 144.4(17) yes
    C6 H6 O6 1_645 0.95 2.53 3.339(2) 143 y
    C16 H16 O7 1_545 0.95 2.38 3.2330(18) 149 y
    C26 H26C O4 1_465 0.98 2.41 3.358(2) 162 y
    C32 H32 O3 1_455 0.95 2.38 3.2715(19) 155 y
    C3 H3 F1 2_756 0.95 2.76 3.308(2) 118 y
    C29 H29 F1 2_666 0.95 2.66 3.3715(19) 133 y
    C13 H13 F2 2_666 0.95 2.75 3.4627(19) 133 y
    C19 H19 F2 2_666 0.95 2.69 3.223(2) 116 y
data_global
_journal_date_recd_electronic     2009-03-11
_journal_date_accepted     2009-03-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      4
_journal_page_first     o858
_journal_page_last     o859
_journal_paper_category     QO
_journal_coeditor_code     NC2138
_publ_contact_author_name
;
'Hameed, Shahid'
;
_publ_contact_author_address
;
Department of Chemistry
Quaid-i-Azam University
Islamabad-45320
Pakistan
;
_publ_contact_author_email     'shameed@qau.edu.pk'
_publ_contact_author_fax     '+92 51 9064 4421'
_publ_contact_author_phone     '+92 51 9064 2133'
_publ_section_title
;
1-(4-Chlorophenylsulfonyl)-5-(4-fluorophenyl)-5-methylimidazolidine-2,4-dione
;
loop_
    _publ_author_name
    _publ_author_address
    'Hussain, Abid'
;
Department of Chemistry
Quaid-i-Azam University
Islamabad 45320
Pakistan
;
    'Hameed, Shahid'
;
Department of Chemistry
Quaid-i-Azam University
Islamabad 45320
Pakistan
;
    'Stoeckli-Evans, Helen'
;
Institute of Physics,
University of Neuchâtel
rue Emile-Argand 11
CH-2009 Neuchâtel
Switzerland
;
