##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-12-06
_journal_date_accepted     2013-01-23
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2013
_journal_volume     69
_journal_issue      3
_journal_page_first     267
_journal_page_last     272
_journal_paper_category     FO
_journal_paper_doi     10.1107/S0108270113002291
_journal_coeditor_code     UK3058
_publ_contact_author_name     'Martins, F. T.'
_publ_contact_author_address
;
Universidade Federal de Goias
Instituto de Química
Campus Samambaia
CP 131
CEP 74001-970
Goiania/GO
Brazil
;
_publ_contact_author_email     felipetmartins@yahoo.com.br
_publ_contact_author_fax     '+55(62)3521 1097'
_publ_contact_author_phone     '+55(62)3521 1167'
_publ_section_title
;
An additional methylene group driving the conformation and assembly of two
arylsulfonamide para-alkoxychalcone hybrids
;
loop_
    _publ_author_name
    _publ_author_address
    'de Castro, Mirian R. C.'
;
Institute of Chemistry
Federal University of Goiás
Goiânia
GO 74001-970
Brazil
;
    'Aragão, Angelo Q.'
;
Science and Technology Center
State University of Goiás
Anápolis
GO 75132-903
Brazil
;
    'Napolitano, Hamilton B.'
;
Science and Technology Center
State University of Goiás
Anápolis
GO 75132-903
Brazil
;
    'Noda-Perez, Caridad'
;
Institute of Chemistry
Federal University of Goiás
Goiânia
GO 74001-970
Brazil
;
    'Martins, Felipe T.'
;
Institute of Chemistry
Federal University of Goiás
Goiânia
GO 74001-970
Brazil
;
data_I
_chemical_name_systematic
;\
N-{4-[(E)-3-(4-Methoxyphenyl)prop-2-\
enoyl]phenyl}benzenesulfonamide
;
_chemical_formula_moiety     'C22 H19 N O4 S'
_chemical_formula_sum     'C22 H19 N O4 S'
_chemical_formula_iupac     'C22 H19 N O4 S'
_chemical_formula_weight     393.44
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_hall     -P1
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     11.8650(3)
_cell_length_b     12.2420(3)
_cell_length_c     14.7287(3)
_cell_angle_alpha     68.0750(10)
_cell_angle_beta     81.6650(10)
_cell_angle_gamma     80.4370(10)
_cell_volume     1948.99(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6621
_cell_measurement_theta_min     2.402
_cell_measurement_theta_max     22.750
_cell_measurement_temperature     298(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.341
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     824
_exptl_absorpt_coefficient_mu     0.194
_exptl_absorpt_correction_type     none
_exptl_special_details     ?
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     CCD
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     22723
_diffrn_reflns_av_R_equivalents     0.0394
_diffrn_reflns_theta_min     1.5
_diffrn_reflns_theta_max     26.92
_diffrn_reflns_theta_full     26.92
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     17
_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     8378
_reflns_number_gt     5268
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0921
_refine_ls_R_factor_gt     0.0535
_refine_ls_wR_factor_ref     0.1516
_refine_ls_goodness_of_fit_ref     1.015
_refine_ls_restrained_S_all     1.015
_refine_ls_number_reflns     8378
_refine_ls_number_parameters     512
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0555P)²+0.7349P] 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
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.242
_refine_diff_density_min     -0.265
_refine_ls_extinction_method     none
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.006 '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'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 2000)'
_computing_cell_refinement     'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction
                            'HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 S1A 0.17904(5) 0.79421(6) -0.03767(5) 0.0646(2) Uani d . 1 . .
    S S1B 0.36203(6) 0.34197(7) 0.55077(5) 0.0694(2) Uani d . 1 . .
    O O3B 0.52135(14) 0.35404(17) 0.02461(12) 0.0722(5) Uani d . 1 . .
    O O2B 0.25459(15) 0.40900(18) 0.52211(13) 0.0816(6) Uani d . 1 . .
    O O1B 0.41481(16) 0.3584(2) 0.62501(13) 0.0854(6) Uani d . 1 . .
    N N1A 0.24599(18) 0.70776(19) 0.05831(16) 0.0661(6) Uani d . 1 . .
    O O1A 0.21279(16) 0.73965(17) -0.10896(14) 0.0795(5) Uani d . 1 . .
    O O2A 0.05999(14) 0.81540(18) -0.00745(14) 0.0799(5) Uani d . 1 . .
    O O4B -0.05735(17) 0.4984(2) -0.28263(16) 0.0947(6) Uani d . 1 . .
    O O3A 0.31611(18) 0.7139(2) 0.47768(16) 0.1072(8) Uani d . 1 . .
    C C7B 0.4446(2) 0.3629(2) 0.36402(17) 0.0602(6) Uani d . 1 . .
    C C16B 0.2188(2) 0.4344(2) -0.11850(18) 0.0582(6) Uani d . 1 . .
    C C17B 0.2373(2) 0.4527(2) -0.21827(18) 0.0635(6) Uani d . 1 . .
    H H17B 0.3123 0.4498 -0.2471 0.076 Uiso calc R 1 . .
    N N1B 0.45667(19) 0.3690(2) 0.45617(16) 0.0751(7) Uani d . 1 . .
    C C11B 0.3353(2) 0.3661(3) 0.23888(19) 0.0766(8) Uani d . 1 . .
    H H11B 0.2642 0.3687 0.218 0.092 Uiso calc R 1 . .
    C C7A 0.2392(2) 0.7274(2) 0.14772(18) 0.0602(6) Uani d . 1 . .
    C C21B 0.1051(2) 0.4378(2) -0.0777(2) 0.0706(7) Uani d . 1 . .
    H H21B 0.0897 0.425 -0.011 0.085 Uiso calc R 1 . .
    C C12B 0.3402(2) 0.3639(3) 0.3323(2) 0.0850(9) Uani d . 1 . .
    H H12B 0.2734 0.3631 0.3741 0.102 Uiso calc R 1 . .
    C C15B 0.3171(2) 0.4082(2) -0.06264(18) 0.0601(6) Uani d . 1 . .
    H H15B 0.3879 0.3988 -0.0971 0.072 Uiso calc R 1 . .
    C C18B 0.1485(2) 0.4750(2) -0.27569(19) 0.0689(7) Uani d . 1 . .
    H H18B 0.1635 0.4873 -0.3423 0.083 Uiso calc R 1 . .
    C C8B 0.5424(2) 0.3574(2) 0.30272(18) 0.0647(6) Uani d . 1 . .
    H H8B 0.6135 0.3533 0.3242 0.078 Uiso calc R 1 . .
    C C13B 0.4309(2) 0.3695(2) 0.07319(17) 0.0565(6) Uani d . 1 . .
    C C9B 0.5370(2) 0.3578(2) 0.21029(18) 0.0630(6) Uani d . 1 . .
    H H9B 0.6046 0.3535 0.1703 0.076 Uiso calc R 1 . .
    C C1A 0.2357(2) 0.9295(2) -0.07958(17) 0.0630(6) Uani d . 1 . .
    C C10B 0.43259(19) 0.3645(2) 0.17527(17) 0.0546(5) Uani d . 1 . .
    O O4A -0.2762(2) 0.9286(3) 0.78912(19) 0.1242(9) Uani d . 1 . .
    C C14B 0.3211(2) 0.3955(2) 0.03014(18) 0.0618(6) Uani d . 1 . .
    H H14B 0.253 0.4032 0.0687 0.074 Uiso calc R 1 . .
    C C13A 0.2292(3) 0.7493(3) 0.4336(2) 0.0765(8) Uani d . 1 . .
    C C10A 0.2314(2) 0.7464(2) 0.3332(2) 0.0689(7) Uani d . 1 . .
    C C16A 0.0107(3) 0.8190(2) 0.62976(19) 0.0719(7) Uani d . 1 . .
    C C6A 0.1643(3) 1.0319(3) -0.0857(2) 0.0810(8) Uani d . 1 . .
    H H6A 0.0865 1.0294 -0.0652 0.097 Uiso calc R 1 . .
    C C11A 0.1398(2) 0.7892(3) 0.2768(2) 0.0840(9) Uani d . 1 . .
    H H11A 0.0735 0.826 0.3007 0.101 Uiso calc R 1 . .
    C C21A -0.0923(3) 0.8748(3) 0.5895(2) 0.0926(9) Uani d . 1 . .
    H H21A -0.0983 0.889 0.5237 0.111 Uiso calc R 1 . .
    C C15A 0.1104(3) 0.7821(3) 0.5737(2) 0.0760(8) Uani d . 1 . .
    H H15A 0.1746 0.7466 0.6083 0.091 Uiso calc R 1 . .
    C C1B 0.3442(3) 0.1908(3) 0.58692(18) 0.0731(7) Uani d . 1 . .
    C C5A 0.2092(3) 1.1388(3) -0.1228(3) 0.0997(10) Uani d . 1 . .
    H H5A 0.1613 1.2089 -0.1283 0.12 Uiso calc R 1 . .
    C C19B 0.0369(2) 0.4788(2) -0.2336(2) 0.0690(7) Uani d . 1 . .
    C C12A 0.1428(2) 0.7795(3) 0.1863(2) 0.0888(9) Uani d . 1 . .
    H H12A 0.0786 0.8086 0.1509 0.107 Uiso calc R 1 . .
    C C8A 0.3326(2) 0.6855(3) 0.2022(2) 0.0859(9) Uani d . 1 . .
    H H8A 0.3995 0.6507 0.1773 0.103 Uiso calc R 1 . .
    C C17A 0.0138(3) 0.8004(3) 0.7279(2) 0.0867(9) Uani d . 1 . .
    H H17A 0.0808 0.7627 0.7575 0.104 Uiso calc R 1 . .
    C C18A -0.0784(3) 0.8354(3) 0.7838(2) 0.0889(9) Uani d . 1 . .
    H H18A -0.0728 0.8222 0.8495 0.107 Uiso calc R 1 . .
    C C19A -0.1785(3) 0.8901(3) 0.7413(2) 0.0907(9) Uani d . 1 . .
    C C2A 0.3500(3) 0.9334(3) -0.1101(3) 0.0908(9) Uani d . 1 . .
    H H2A 0.398 0.864 -0.1067 0.109 Uiso calc R 1 . .
    C C14A 0.1232(3) 0.7920(3) 0.4799(2) 0.0790(8) Uani d . 1 . .
    H H14A 0.0615 0.8277 0.4421 0.095 Uiso calc R 1 . .
    C C22B -0.0381(3) 0.5009(3) -0.3814(3) 0.1051(11) Uani d . 1 . .
    H H22A -0.1104 0.5143 -0.408 0.158 Uiso calc R 1 . .
    H H22B 0.0024 0.4265 -0.382 0.158 Uiso calc R 1 . .
    H H22C 0.0067 0.5638 -0.4203 0.158 Uiso calc R 1 . .
    C C20B 0.0157(2) 0.4595(3) -0.1338(2) 0.0755(8) Uani d . 1 . .
    H H20B -0.0594 0.4612 -0.1051 0.091 Uiso calc R 1 . .
    C C4A 0.3235(4) 1.1419(3) -0.1512(2) 0.0980(10) Uani d . 1 . .
    H H4A 0.3538 1.2138 -0.1744 0.118 Uiso calc R 1 . .
    C C4B 0.3128(6) -0.0426(4) 0.6518(3) 0.1318(15) Uani d . 1 . .
    H H4B 0.302 -0.1222 0.6734 0.158 Uiso calc R 1 . .
    C C3A 0.3934(3) 1.0399(3) -0.1455(3) 0.1055(11) Uani d . 1 . .
    H H3A 0.4712 1.0425 -0.1659 0.127 Uiso calc R 1 . .
    C C9A 0.3279(3) 0.6945(3) 0.2930(2) 0.0925(10) Uani d . 1 . .
    H H9A 0.3919 0.6646 0.3286 0.111 Uiso calc R 1 . .
    C C20A -0.1851(3) 0.9093(3) 0.6440(3) 0.1008(10) Uani d . 1 . .
    H H20A -0.2528 0.9459 0.6151 0.121 Uiso calc R 1 . .
    C C6B 0.2361(3) 0.1570(4) 0.6157(2) 0.0991(10) Uani d . 1 . .
    H H6B 0.1729 0.2142 0.6121 0.119 Uiso calc R 1 . .
    C C5B 0.2204(4) 0.0392(5) 0.6498(3) 0.1245(15) Uani d . 1 . .
    H H5B 0.1474 0.0161 0.6711 0.149 Uiso calc R 1 . .
    C C3B 0.4211(5) -0.0121(4) 0.6233(4) 0.1494(19) Uani d . 1 . .
    H H3B 0.4834 -0.0698 0.6251 0.179 Uiso calc R 1 . .
    C C2B 0.4373(4) 0.1087(4) 0.5910(3) 0.1212(13) Uani d . 1 . .
    H H2B 0.5106 0.1316 0.5727 0.145 Uiso calc R 1 . .
    C C22A -0.2706(4) 0.9231(4) 0.8865(3) 0.1404(16) Uani d . 1 . .
    H H22D -0.344 0.953 0.9108 0.211 Uiso calc R 1 . .
    H H22E -0.2136 0.9704 0.8865 0.211 Uiso calc R 1 . .
    H H22F -0.2505 0.8423 0.928 0.211 Uiso calc R 1 . .
    H H1B 0.521(4) 0.361(4) 0.471(3) 0.169 Uiso d . 1 . .
    H H1A 0.308(4) 0.679(4) 0.040(3) 0.169 Uiso d . 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'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
    S1A O1A . 1.4220(18) ?
    S1A O2A . 1.4293(17) ?
    S1A N1A . 1.637(2) ?
    S1A C1A . 1.749(3) ?
    S1B O2B . 1.4235(19) ?
    S1B O1B . 1.4258(18) ?
    S1B N1B . 1.624(2) ?
    S1B C1B . 1.764(3) ?
    O3B C13B . 1.229(3) ?
    N1A C7A . 1.414(3) ?
    N1A H1A . 0.82(4) ?
    O4B C19B . 1.359(3) ?
    O4B C22B . 1.428(4) ?
    O3A C13A . 1.228(3) ?
    C7B C8B . 1.372(3) ?
    C7B C12B . 1.382(3) ?
    C7B N1B . 1.416(3) ?
    C16B C17B . 1.391(3) ?
    C16B C21B . 1.396(3) ?
    C16B C15B . 1.447(3) ?
    C17B C18B . 1.375(3) ?
    C17B H17B . 0.93 ?
    N1B H1B . 0.80(4) ?
    C11B C12B . 1.376(4) ?
    C11B C10B . 1.380(3) ?
    C11B H11B . 0.93 ?
    C7A C12A . 1.371(4) ?
    C7A C8A . 1.377(3) ?
    C21B C20B . 1.370(4) ?
    C21B H21B . 0.93 ?
    C12B H12B . 0.93 ?
    C15B C14B . 1.323(3) ?
    C15B H15B . 0.93 ?
    C18B C19B . 1.379(4) ?
    C18B H18B . 0.93 ?
    C8B C9B . 1.370(3) ?
    C8B H8B . 0.93 ?
    C13B C14B . 1.467(3) ?
    C13B C10B . 1.485(3) ?
    C9B C10B . 1.389(3) ?
    C9B H9B . 0.93 ?
    C1A C2A . 1.368(4) ?
    C1A C6A . 1.372(4) ?
    O4A C19A . 1.375(4) ?
    O4A C22A . 1.421(4) ?
    C14B H14B . 0.93 ?
    C13A C14A . 1.456(4) ?
    C13A C10A . 1.489(4) ?
    C10A C11A . 1.376(4) ?
    C10A C9A . 1.381(4) ?
    C16A C17A . 1.381(4) ?
    C16A C21A . 1.393(4) ?
    C16A C15A . 1.451(4) ?
    C6A C5A . 1.382(4) ?
    C6A H6A . 0.93 ?
    C11A C12A . 1.377(4) ?
    C11A H11A . 0.93 ?
    C21A C20A . 1.371(4) ?
    C21A H21A . 0.93 ?
    C15A C14A . 1.330(4) ?
    C15A H15A . 0.93 ?
    C1B C2B . 1.356(4) ?
    C1B C6B . 1.373(4) ?
    C5A C4A . 1.362(5) ?
    C5A H5A . 0.93 ?
    C19B C20B . 1.389(4) ?
    C12A H12A . 0.93 ?
    C8A C9A . 1.375(4) ?
    C8A H8A . 0.93 ?
    C17A C18A . 1.381(4) ?
    C17A H17A . 0.93 ?
    C18A C19A . 1.374(4) ?
    C18A H18A . 0.93 ?
    C19A C20A . 1.374(4) ?
    C2A C3A . 1.369(4) ?
    C2A H2A . 0.93 ?
    C14A H14A . 0.93 ?
    C22B H22A . 0.96 ?
    C22B H22B . 0.96 ?
    C22B H22C . 0.96 ?
    C20B H20B . 0.93 ?
    C4A C3A . 1.361(5) ?
    C4A H4A . 0.93 ?
    C4B C5B . 1.351(6) ?
    C4B C3B . 1.362(6) ?
    C4B H4B . 0.93 ?
    C3A H3A . 0.93 ?
    C9A H9A . 0.93 ?
    C20A H20A . 0.93 ?
    C6B C5B . 1.374(5) ?
    C6B H6B . 0.93 ?
    C5B H5B . 0.93 ?
    C3B C2B . 1.411(6) ?
    C3B H3B . 0.93 ?
    C2B H2B . 0.93 ?
    C22A H22D . 0.96 ?
    C22A H22E . 0.96 ?
    C22A H22F . 0.96 ?
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
    O1A S1A O2A . . 119.61(12) ?
    O1A S1A N1A . . 104.80(11) ?
    O2A S1A N1A . . 109.01(11) ?
    O1A S1A C1A . . 108.43(12) ?
    O2A S1A C1A . . 107.90(12) ?
    N1A S1A C1A . . 106.36(12) ?
    O2B S1B O1B . . 119.17(12) ?
    O2B S1B N1B . . 109.69(12) ?
    O1B S1B N1B . . 105.01(12) ?
    O2B S1B C1B . . 107.17(13) ?
    O1B S1B C1B . . 109.08(13) ?
    N1B S1B C1B . . 106.03(13) ?
    C7A N1A S1A . . 125.13(17) ?
    C7A N1A H1A . . 116(3) ?
    S1A N1A H1A . . 110(3) ?
    C19B O4B C22B . . 116.9(2) ?
    C8B C7B C12B . . 118.7(2) ?
    C8B C7B N1B . . 117.6(2) ?
    C12B C7B N1B . . 123.7(2) ?
    C17B C16B C21B . . 117.1(2) ?
    C17B C16B C15B . . 118.8(2) ?
    C21B C16B C15B . . 124.0(2) ?
    C18B C17B C16B . . 122.3(2) ?
    C18B C17B H17B . . 118.9 ?
    C16B C17B H17B . . 118.9 ?
    C7B N1B S1B . . 126.34(18) ?
    C7B N1B H1B . . 117(3) ?
    S1B N1B H1B . . 112(3) ?
    C12B C11B C10B . . 121.9(2) ?
    C12B C11B H11B . . 119 ?
    C10B C11B H11B . . 119 ?
    C12A C7A C8A . . 117.9(3) ?
    C12A C7A N1A . . 123.8(2) ?
    C8A C7A N1A . . 118.1(2) ?
    C20B C21B C16B . . 121.3(2) ?
    C20B C21B H21B . . 119.3 ?
    C16B C21B H21B . . 119.3 ?
    C11B C12B C7B . . 120.0(2) ?
    C11B C12B H12B . . 120 ?
    C7B C12B H12B . . 120 ?
    C14B C15B C16B . . 129.6(2) ?
    C14B C15B H15B . . 115.2 ?
    C16B C15B H15B . . 115.2 ?
    C17B C18B C19B . . 119.4(2) ?
    C17B C18B H18B . . 120.3 ?
    C19B C18B H18B . . 120.3 ?
    C9B C8B C7B . . 121.0(2) ?
    C9B C8B H8B . . 119.5 ?
    C7B C8B H8B . . 119.5 ?
    O3B C13B C14B . . 120.4(2) ?
    O3B C13B C10B . . 120.0(2) ?
    C14B C13B C10B . . 119.7(2) ?
    C8B C9B C10B . . 121.2(2) ?
    C8B C9B H9B . . 119.4 ?
    C10B C9B H9B . . 119.4 ?
    C2A C1A C6A . . 120.3(3) ?
    C2A C1A S1A . . 119.9(2) ?
    C6A C1A S1A . . 119.8(2) ?
    C11B C10B C9B . . 117.1(2) ?
    C11B C10B C13B . . 123.7(2) ?
    C9B C10B C13B . . 119.2(2) ?
    C19A O4A C22A . . 118.1(3) ?
    C15B C14B C13B . . 121.2(2) ?
    C15B C14B H14B . . 119.4 ?
    C13B C14B H14B . . 119.4 ?
    O3A C13A C14A . . 120.3(3) ?
    O3A C13A C10A . . 119.9(3) ?
    C14A C13A C10A . . 119.7(2) ?
    C11A C10A C9A . . 116.1(3) ?
    C11A C10A C13A . . 123.9(3) ?
    C9A C10A C13A . . 120.0(3) ?
    C17A C16A C21A . . 116.1(3) ?
    C17A C16A C15A . . 120.7(3) ?
    C21A C16A C15A . . 123.2(3) ?
    C1A C6A C5A . . 119.2(3) ?
    C1A C6A H6A . . 120.4 ?
    C5A C6A H6A . . 120.4 ?
    C10A C11A C12A . . 122.3(3) ?
    C10A C11A H11A . . 118.8 ?
    C12A C11A H11A . . 118.8 ?
    C20A C21A C16A . . 121.9(3) ?
    C20A C21A H21A . . 119 ?
    C16A C21A H21A . . 119 ?
    C14A C15A C16A . . 129.1(3) ?
    C14A C15A H15A . . 115.4 ?
    C16A C15A H15A . . 115.4 ?
    C2B C1B C6B . . 120.6(3) ?
    C2B C1B S1B . . 120.0(3) ?
    C6B C1B S1B . . 119.3(3) ?
    C4A C5A C6A . . 120.2(3) ?
    C4A C5A H5A . . 119.9 ?
    C6A C5A H5A . . 119.9 ?
    O4B C19B C18B . . 124.5(3) ?
    O4B C19B C20B . . 115.7(3) ?
    C18B C19B C20B . . 119.7(2) ?
    C7A C12A C11A . . 120.8(3) ?
    C7A C12A H12A . . 119.6 ?
    C11A C12A H12A . . 119.6 ?
    C9A C8A C7A . . 120.6(3) ?
    C9A C8A H8A . . 119.7 ?
    C7A C8A H8A . . 119.7 ?
    C18A C17A C16A . . 122.8(3) ?
    C18A C17A H17A . . 118.6 ?
    C16A C17A H17A . . 118.6 ?
    C19A C18A C17A . . 119.2(3) ?
    C19A C18A H18A . . 120.4 ?
    C17A C18A H18A . . 120.4 ?
    C20A C19A C18A . . 119.6(3) ?
    C20A C19A O4A . . 115.6(3) ?
    C18A C19A O4A . . 124.8(3) ?
    C1A C2A C3A . . 119.7(3) ?
    C1A C2A H2A . . 120.1 ?
    C3A C2A H2A . . 120.1 ?
    C15A C14A C13A . . 122.9(3) ?
    C15A C14A H14A . . 118.5 ?
    C13A C14A H14A . . 118.5 ?
    O4B C22B H22A . . 109.5 ?
    O4B C22B H22B . . 109.5 ?
    H22A C22B H22B . . 109.5 ?
    O4B C22B H22C . . 109.5 ?
    H22A C22B H22C . . 109.5 ?
    H22B C22B H22C . . 109.5 ?
    C21B C20B C19B . . 120.2(2) ?
    C21B C20B H20B . . 119.9 ?
    C19B C20B H20B . . 119.9 ?
    C3A C4A C5A . . 120.1(3) ?
    C3A C4A H4A . . 120 ?
    C5A C4A H4A . . 120 ?
    C5B C4B C3B . . 122.0(5) ?
    C5B C4B H4B . . 119 ?
    C3B C4B H4B . . 119 ?
    C4A C3A C2A . . 120.4(3) ?
    C4A C3A H3A . . 119.8 ?
    C2A C3A H3A . . 119.8 ?
    C8A C9A C10A . . 122.3(3) ?
    C8A C9A H9A . . 118.9 ?
    C10A C9A H9A . . 118.9 ?
    C21A C20A C19A . . 120.3(3) ?
    C21A C20A H20A . . 119.9 ?
    C19A C20A H20A . . 119.9 ?
    C1B C6B C5B . . 120.5(4) ?
    C1B C6B H6B . . 119.7 ?
    C5B C6B H6B . . 119.7 ?
    C4B C5B C6B . . 119.0(4) ?
    C4B C5B H5B . . 120.5 ?
    C6B C5B H5B . . 120.5 ?
    C4B C3B C2B . . 118.9(4) ?
    C4B C3B H3B . . 120.6 ?
    C2B C3B H3B . . 120.6 ?
    C1B C2B C3B . . 119.0(4) ?
    C1B C2B H2B . . 120.5 ?
    C3B C2B H2B . . 120.5 ?
    O4A C22A H22D . . 109.5 ?
    O4A C22A H22E . . 109.5 ?
    H22D C22A H22E . . 109.5 ?
    O4A C22A H22F . . 109.5 ?
    H22D C22A H22F . . 109.5 ?
    H22E C22A H22F . . 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
    O1A S1A N1A C7A . . . . 179.4(2) ?
    O2A S1A N1A C7A . . . . -51.5(2) ?
    C1A S1A N1A C7A . . . . 64.6(2) ?
    C21B C16B C17B C18B . . . . 0.9(4) ?
    C15B C16B C17B C18B . . . . 178.3(2) ?
    C8B C7B N1B S1B . . . . -162.9(2) ?
    C12B C7B N1B S1B . . . . 18.1(4) ?
    O2B S1B N1B C7B . . . . -51.6(3) ?
    O1B S1B N1B C7B . . . . 179.2(2) ?
    C1B S1B N1B C7B . . . . 63.8(3) ?
    S1A N1A C7A C12A . . . . 33.5(4) ?
    S1A N1A C7A C8A . . . . -150.6(2) ?
    C17B C16B C21B C20B . . . . -0.7(4) ?
    C15B C16B C21B C20B . . . . -177.9(3) ?
    C10B C11B C12B C7B . . . . 1.5(5) ?
    C8B C7B C12B C11B . . . . -3.6(5) ?
    N1B C7B C12B C11B . . . . 175.4(3) ?
    C17B C16B C15B C14B . . . . 175.0(3) ?
    C21B C16B C15B C14B . . . . -7.9(4) ?
    C16B C17B C18B C19B . . . . -0.4(4) ?
    C12B C7B C8B C9B . . . . 2.7(4) ?
    N1B C7B C8B C9B . . . . -176.4(2) ?
    C7B C8B C9B C10B . . . . 0.4(4) ?
    O1A S1A C1A C2A . . . . -51.2(3) ?
    O2A S1A C1A C2A . . . . 177.8(2) ?
    N1A S1A C1A C2A . . . . 61.0(3) ?
    O1A S1A C1A C6A . . . . 125.9(2) ?
    O2A S1A C1A C6A . . . . -5.0(2) ?
    N1A S1A C1A C6A . . . . -121.8(2) ?
    C12B C11B C10B C9B . . . . 1.5(4) ?
    C12B C11B C10B C13B . . . . -178.6(3) ?
    C8B C9B C10B C11B . . . . -2.5(4) ?
    C8B C9B C10B C13B . . . . 177.6(2) ?
    O3B C13B C10B C11B . . . . -171.6(2) ?
    C14B C13B C10B C11B . . . . 9.8(4) ?
    O3B C13B C10B C9B . . . . 8.3(3) ?
    C14B C13B C10B C9B . . . . -170.3(2) ?
    C16B C15B C14B C13B . . . . -179.5(2) ?
    O3B C13B C14B C15B . . . . -3.1(4) ?
    C10B C13B C14B C15B . . . . 175.5(2) ?
    O3A C13A C10A C11A . . . . -177.0(3) ?
    C14A C13A C10A C11A . . . . 4.3(4) ?
    O3A C13A C10A C9A . . . . 5.6(5) ?
    C14A C13A C10A C9A . . . . -173.1(3) ?
    C2A C1A C6A C5A . . . . -0.2(4) ?
    S1A C1A C6A C5A . . . . -177.4(2) ?
    C9A C10A C11A C12A . . . . 1.0(5) ?
    C13A C10A C11A C12A . . . . -176.5(3) ?
    C17A C16A C21A C20A . . . . 0.1(5) ?
    C15A C16A C21A C20A . . . . -179.6(3) ?
    C17A C16A C15A C14A . . . . 179.6(3) ?
    C21A C16A C15A C14A . . . . -0.7(5) ?
    O2B S1B C1B C2B . . . . 161.1(3) ?
    O1B S1B C1B C2B . . . . -68.6(3) ?
    N1B S1B C1B C2B . . . . 44.0(3) ?
    O2B S1B C1B C6B . . . . -22.3(3) ?
    O1B S1B C1B C6B . . . . 108.0(2) ?
    N1B S1B C1B C6B . . . . -139.4(2) ?
    C1A C6A C5A C4A . . . . -1.1(5) ?
    C22B O4B C19B C18B . . . . 7.7(4) ?
    C22B O4B C19B C20B . . . . -170.9(3) ?
    C17B C18B C19B O4B . . . . -179.0(3) ?
    C17B C18B C19B C20B . . . . -0.4(4) ?
    C8A C7A C12A C11A . . . . -0.1(5) ?
    N1A C7A C12A C11A . . . . 175.9(3) ?
    C10A C11A C12A C7A . . . . -0.9(5) ?
    C12A C7A C8A C9A . . . . 0.8(5) ?
    N1A C7A C8A C9A . . . . -175.3(3) ?
    C21A C16A C17A C18A . . . . -0.7(5) ?
    C15A C16A C17A C18A . . . . 179.1(3) ?
    C16A C17A C18A C19A . . . . 0.7(5) ?
    C17A C18A C19A C20A . . . . -0.2(5) ?
    C17A C18A C19A O4A . . . . 179.7(3) ?
    C22A O4A C19A C20A . . . . -173.2(3) ?
    C22A O4A C19A C18A . . . . 6.9(5) ?
    C6A C1A C2A C3A . . . . 0.9(5) ?
    S1A C1A C2A C3A . . . . 178.1(3) ?
    C16A C15A C14A C13A . . . . -179.4(3) ?
    O3A C13A C14A C15A . . . . -8.1(5) ?
    C10A C13A C14A C15A . . . . 170.6(3) ?
    C16B C21B C20B C19B . . . . -0.1(4) ?
    O4B C19B C20B C21B . . . . 179.4(3) ?
    C18B C19B C20B C21B . . . . 0.7(4) ?
    C6A C5A C4A C3A . . . . 1.7(5) ?
    C5A C4A C3A C2A . . . . -0.9(6) ?
    C1A C2A C3A C4A . . . . -0.4(6) ?
    C7A C8A C9A C10A . . . . -0.7(5) ?
    C11A C10A C9A C8A . . . . -0.2(5) ?
    C13A C10A C9A C8A . . . . 177.4(3) ?
    C16A C21A C20A C19A . . . . 0.4(6) ?
    C18A C19A C20A C21A . . . . -0.3(5) ?
    O4A C19A C20A C21A . . . . 179.7(3) ?
    C2B C1B C6B C5B . . . . 0.5(5) ?
    S1B C1B C6B C5B . . . . -176.1(3) ?
    C3B C4B C5B C6B . . . . 1.6(7) ?
    C1B C6B C5B C4B . . . . -1.9(6) ?
    C5B C4B C3B C2B . . . . 0.2(8) ?
    C6B C1B C2B C3B . . . . 1.3(6) ?
    S1B C1B C2B C3B . . . . 177.9(3) ?
    C4B C3B C2B C1B . . . . -1.6(7) ?
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
    N1A H1A O3B 2_665 0.81(5) 2.16(5) 2.950(3) 166(5) yes
    N1B H1B O3A 2_666 0.81(5) 2.11(5) 2.892(3) 163(5) yes
    C9A H9A O1B 2_666 0.93 2.43 3.320(4) 160 yes
    C9B H9B O1A 2_665 0.93 2.49 3.366(3) 157 yes
    C22B H22A O2B 2_565 0.96 2.40 3.317(4) 160 yes
    C22A H22D CgA 2_576 0.96 3.28 3.580(4) 101 yes
    C22A H22E CgA 2_576 0.96 3.33 3.580(4) 97 yes
data_II
_chemical_name_systematic
;\
N-{4-[(E)-3-(4-Ethoxyphenyl)prop-2-\
enoyl]phenyl}benzenesulfonamide
;
_chemical_formula_moiety     'C23 H21 N O4 S'
_chemical_formula_sum     'C23 H21 N O4 S'
_chemical_formula_iupac     'C23 H21 N O4 S'
_chemical_formula_weight     407.47
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_hall     -P2ybc
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     8.4506(2)
_cell_length_b     20.1587(6)
_cell_length_c     14.2120(3)
_cell_angle_alpha     90
_cell_angle_beta     119.098(2)
_cell_angle_gamma     90
_cell_volume     2115.49(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4266
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     26.373
_cell_measurement_temperature     298(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.279
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     856
_exptl_absorpt_coefficient_mu     0.181
_exptl_absorpt_correction_type     none
_exptl_special_details     ?
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     CCD
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     7397
_diffrn_reflns_av_R_equivalents     0.0356
_diffrn_reflns_theta_min     3.16
_diffrn_reflns_theta_max     26.38
_diffrn_reflns_theta_full     26.38
_diffrn_measured_fraction_theta_max     0.966
_diffrn_measured_fraction_theta_full     0.966
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     25
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_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     4185
_reflns_number_gt     3072
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0701
_refine_ls_R_factor_gt     0.0489
_refine_ls_wR_factor_ref     0.1432
_refine_ls_goodness_of_fit_ref     1.046
_refine_ls_restrained_S_all     1.046
_refine_ls_number_reflns     4185
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0875P)²+0.0704P] 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
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.17
_refine_diff_density_min     -0.273
_refine_ls_extinction_method     none
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.006 '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'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 2000)'
_computing_cell_refinement     'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction
                            'HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 0.65679(6) 0.11848(2) 0.42888(3) 0.05750(19) Uani d . 1 . .
    N N1 0.76455(19) 0.16732(8) 0.53375(12) 0.0606(4) Uani d . 1 . .
    O O1 0.69037(17) 0.14641(6) 0.34799(10) 0.0709(4) Uani d . 1 . .
    O O2 0.70805(17) 0.05154(6) 0.46160(10) 0.0678(3) Uani d . 1 . .
    O O4 0.74263(19) -0.16891(7) 1.27909(10) 0.0753(4) Uani d . 1 . .
    C C1 0.4242(2) 0.12732(8) 0.38628(13) 0.0546(4) Uani d . 1 . .
    C C7 0.7578(2) 0.15805(8) 0.63097(14) 0.0565(4) Uani d . 1 . .
    C C6 0.3341(2) 0.07890(9) 0.41042(16) 0.0677(5) Uani d . 1 . .
    H H6 0.395 0.0414 0.4491 0.081 Uiso calc R 1 . .
    C C13 0.7446(3) 0.13877(10) 0.92840(15) 0.0660(5) Uani d . 1 . .
    C C21 0.7434(3) -0.05952(10) 1.07881(15) 0.0723(5) Uani d . 1 . .
    H H21 0.7525 -0.0638 1.0165 0.087 Uiso calc R 1 . .
    C C10 0.7513(2) 0.14366(9) 0.82493(14) 0.0601(4) Uani d . 1 . .
    C C19 0.7346(2) -0.11021(9) 1.22857(14) 0.0640(5) Uani d . 1 . .
    O O3 0.7338(2) 0.18963(7) 0.97259(11) 0.0833(4) Uani d . 1 . .
    C C22 0.7544(3) -0.16605(10) 1.38310(15) 0.0747(5) Uani d . 1 . .
    H H22A 0.6452 -0.1466 1.3774 0.09 Uiso calc R 1 . .
    H H22B 0.8569 -0.139 1.4315 0.09 Uiso calc R 1 . .
    C C15 0.7296(3) 0.06480(10) 1.06029(15) 0.0700(5) Uani d . 1 . .
    H H15 0.7149 0.1035 1.0908 0.084 Uiso calc R 1 . .
    C C9 0.7312(3) 0.20515(9) 0.77736(16) 0.0722(5) Uani d . 1 . .
    H H9 0.7166 0.2424 0.8109 0.087 Uiso calc R 1 . .
    C C18 0.7174(3) -0.04923(9) 1.26476(15) 0.0693(5) Uani d . 1 . .
    H H18 0.7081 -0.0455 1.3271 0.083 Uiso calc R 1 . .
    C C17 0.7140(3) 0.00713(10) 1.20731(15) 0.0716(5) Uani d . 1 . .
    H H17 0.7017 0.0484 1.2322 0.086 Uiso calc R 1 . .
    C C8 0.7323(3) 0.21237(9) 0.68120(15) 0.0684(5) Uani d . 1 . .
    H H8 0.7157 0.2541 0.65 0.082 Uiso calc R 1 . .
    C C20 0.7449(3) -0.11520(10) 1.13412(15) 0.0722(5) Uani d . 1 . .
    H H20 0.753 -0.1568 1.1084 0.087 Uiso calc R 1 . .
    C C16 0.7284(2) 0.00392(9) 1.11405(14) 0.0652(5) Uani d . 1 . .
    C C2 0.3369(3) 0.18415(9) 0.33206(16) 0.0700(5) Uani d . 1 . .
    H H2 0.4002 0.2173 0.3189 0.084 Uiso calc R 1 . .
    C C12 0.7835(3) 0.09649(10) 0.67957(16) 0.0743(5) Uani d . 1 . .
    H H12 0.8052 0.0596 0.6482 0.089 Uiso calc R 1 . .
    C C5 0.1508(3) 0.08715(10) 0.37601(17) 0.0754(5) Uani d . 1 . .
    H H5 0.0882 0.055 0.3918 0.09 Uiso calc R 1 . .
    C C14 0.7485(3) 0.07314(10) 0.97391(16) 0.0720(5) Uani d . 1 . .
    H H14 0.7649 0.036 0.9408 0.086 Uiso calc R 1 . .
    C C4 0.0624(3) 0.14239(10) 0.31898(16) 0.0741(5) Uani d . 1 . .
    H H4 -0.061 0.1471 0.2944 0.089 Uiso calc R 1 . .
    C C11 0.7769(3) 0.08960(10) 0.77449(15) 0.0728(5) Uani d . 1 . .
    H H11 0.7901 0.0477 0.8048 0.087 Uiso calc R 1 . .
    C C3 0.1549(3) 0.19133(10) 0.29755(17) 0.0783(5) Uani d . 1 . .
    H H3 0.0941 0.2291 0.2598 0.094 Uiso calc R 1 . .
    C C23 0.7774(4) -0.23565(12) 1.42532(19) 0.0988(7) Uani d . 1 . .
    H H23A 0.7856 -0.2351 1.4951 0.148 Uiso calc R 1 . .
    H H23B 0.8861 -0.2544 1.4309 0.148 Uiso calc R 1 . .
    H H23C 0.6752 -0.2619 1.377 0.148 Uiso calc R 1 . .
    H H1 0.763(3) 0.2108(14) 0.516(2) 0.119 Uiso d . 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'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
    S1 O2 . 1.4245(13) ?
    S1 O1 . 1.4269(12) ?
    S1 N1 . 1.6432(15) ?
    S1 C1 . 1.7621(17) ?
    N1 C7 . 1.423(2) ?
    N1 H1 . 0.91(3) ?
    O4 C19 . 1.369(2) ?
    O4 C22 . 1.434(2) ?
    C1 C2 . 1.378(2) ?
    C1 C6 . 1.380(2) ?
    C7 C8 . 1.380(2) ?
    C7 C12 . 1.385(2) ?
    C6 C5 . 1.388(2) ?
    C6 H6 . 0.93 ?
    C13 O3 . 1.228(2) ?
    C13 C14 . 1.466(3) ?
    C13 C10 . 1.502(2) ?
    C21 C20 . 1.367(3) ?
    C21 C16 . 1.402(2) ?
    C21 H21 . 0.93 ?
    C10 C11 . 1.378(2) ?
    C10 C9 . 1.382(3) ?
    C19 C18 . 1.367(3) ?
    C19 C20 . 1.390(2) ?
    C22 C23 . 1.501(3) ?
    C22 H22A . 0.97 ?
    C22 H22B . 0.97 ?
    C15 C14 . 1.324(3) ?
    C15 C16 . 1.448(2) ?
    C15 H15 . 0.93 ?
    C9 C8 . 1.379(3) ?
    C9 H9 . 0.93 ?
    C18 C17 . 1.391(3) ?
    C18 H18 . 0.93 ?
    C17 C16 . 1.390(2) ?
    C17 H17 . 0.93 ?
    C8 H8 . 0.93 ?
    C20 H20 . 0.93 ?
    C2 C3 . 1.376(3) ?
    C2 H2 . 0.93 ?
    C12 C11 . 1.384(3) ?
    C12 H12 . 0.93 ?
    C5 C4 . 1.366(3) ?
    C5 H5 . 0.93 ?
    C14 H14 . 0.93 ?
    C4 C3 . 1.381(3) ?
    C4 H4 . 0.93 ?
    C11 H11 . 0.93 ?
    C3 H3 . 0.93 ?
    C23 H23A . 0.96 ?
    C23 H23B . 0.96 ?
    C23 H23C . 0.96 ?
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
    O2 S1 O1 . . 119.26(7) ?
    O2 S1 N1 . . 108.97(8) ?
    O1 S1 N1 . . 104.76(8) ?
    O2 S1 C1 . . 108.62(7) ?
    O1 S1 C1 . . 108.00(8) ?
    N1 S1 C1 . . 106.53(7) ?
    C7 N1 S1 . . 122.41(11) ?
    C7 N1 H1 . . 113.0(16) ?
    S1 N1 H1 . . 113.6(17) ?
    C19 O4 C22 . . 117.85(14) ?
    C2 C1 C6 . . 121.14(16) ?
    C2 C1 S1 . . 118.74(12) ?
    C6 C1 S1 . . 120.09(13) ?
    C8 C7 C12 . . 118.61(16) ?
    C8 C7 N1 . . 119.22(15) ?
    C12 C7 N1 . . 122.11(15) ?
    C1 C6 C5 . . 118.90(17) ?
    C1 C6 H6 . . 120.5 ?
    C5 C6 H6 . . 120.5 ?
    O3 C13 C14 . . 121.27(17) ?
    O3 C13 C10 . . 119.55(17) ?
    C14 C13 C10 . . 119.18(16) ?
    C20 C21 C16 . . 121.40(17) ?
    C20 C21 H21 . . 119.3 ?
    C16 C21 H21 . . 119.3 ?
    C11 C10 C9 . . 117.89(16) ?
    C11 C10 C13 . . 123.20(17) ?
    C9 C10 C13 . . 118.90(16) ?
    C18 C19 O4 . . 124.55(16) ?
    C18 C19 C20 . . 119.76(18) ?
    O4 C19 C20 . . 115.69(16) ?
    O4 C22 C23 . . 107.77(16) ?
    O4 C22 H22A . . 110.2 ?
    C23 C22 H22A . . 110.2 ?
    O4 C22 H22B . . 110.2 ?
    C23 C22 H22B . . 110.2 ?
    H22A C22 H22B . . 108.5 ?
    C14 C15 C16 . . 129.19(18) ?
    C14 C15 H15 . . 115.4 ?
    C16 C15 H15 . . 115.4 ?
    C8 C9 C10 . . 121.40(17) ?
    C8 C9 H9 . . 119.3 ?
    C10 C9 H9 . . 119.3 ?
    C19 C18 C17 . . 119.28(16) ?
    C19 C18 H18 . . 120.4 ?
    C17 C18 H18 . . 120.4 ?
    C16 C17 C18 . . 122.35(17) ?
    C16 C17 H17 . . 118.8 ?
    C18 C17 H17 . . 118.8 ?
    C9 C8 C7 . . 120.45(17) ?
    C9 C8 H8 . . 119.8 ?
    C7 C8 H8 . . 119.8 ?
    C21 C20 C19 . . 120.54(17) ?
    C21 C20 H20 . . 119.7 ?
    C19 C20 H20 . . 119.7 ?
    C17 C16 C21 . . 116.63(17) ?
    C17 C16 C15 . . 119.34(17) ?
    C21 C16 C15 . . 124.02(17) ?
    C3 C2 C1 . . 119.25(17) ?
    C3 C2 H2 . . 120.4 ?
    C1 C2 H2 . . 120.4 ?
    C11 C12 C7 . . 120.35(17) ?
    C11 C12 H12 . . 119.8 ?
    C7 C12 H12 . . 119.8 ?
    C4 C5 C6 . . 120.08(17) ?
    C4 C5 H5 . . 120 ?
    C6 C5 H5 . . 120 ?
    C15 C14 C13 . . 122.46(18) ?
    C15 C14 H14 . . 118.8 ?
    C13 C14 H14 . . 118.8 ?
    C5 C4 C3 . . 120.54(18) ?
    C5 C4 H4 . . 119.7 ?
    C3 C4 H4 . . 119.7 ?
    C10 C11 C12 . . 121.23(18) ?
    C10 C11 H11 . . 119.4 ?
    C12 C11 H11 . . 119.4 ?
    C2 C3 C4 . . 120.03(18) ?
    C2 C3 H3 . . 120 ?
    C4 C3 H3 . . 120 ?
    C22 C23 H23A . . 109.5 ?
    C22 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C22 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 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
    O2 S1 N1 C7 . . . . -54.26(15) ?
    O1 S1 N1 C7 . . . . 177.05(13) ?
    C1 S1 N1 C7 . . . . 62.76(15) ?
    O2 S1 C1 C2 . . . . -167.78(14) ?
    O1 S1 C1 C2 . . . . -37.10(16) ?
    N1 S1 C1 C2 . . . . 74.98(15) ?
    O2 S1 C1 C6 . . . . 14.36(17) ?
    O1 S1 C1 C6 . . . . 145.04(14) ?
    N1 S1 C1 C6 . . . . -102.89(15) ?
    S1 N1 C7 C8 . . . . -135.53(15) ?
    S1 N1 C7 C12 . . . . 47.2(2) ?
    C2 C1 C6 C5 . . . . 2.1(3) ?
    S1 C1 C6 C5 . . . . 179.91(14) ?
    O3 C13 C10 C11 . . . . 175.02(19) ?
    C14 C13 C10 C11 . . . . -5.8(3) ?
    O3 C13 C10 C9 . . . . -4.9(3) ?
    C14 C13 C10 C9 . . . . 174.23(18) ?
    C22 O4 C19 C18 . . . . -7.4(3) ?
    C22 O4 C19 C20 . . . . 172.68(17) ?
    C19 O4 C22 C23 . . . . -175.26(17) ?
    C11 C10 C9 C8 . . . . 1.5(3) ?
    C13 C10 C9 C8 . . . . -178.55(16) ?
    O4 C19 C18 C17 . . . . 178.87(18) ?
    C20 C19 C18 C17 . . . . -1.2(3) ?
    C19 C18 C17 C16 . . . . -0.3(3) ?
    C10 C9 C8 C7 . . . . -1.5(3) ?
    C12 C7 C8 C9 . . . . -0.5(3) ?
    N1 C7 C8 C9 . . . . -177.83(16) ?
    C16 C21 C20 C19 . . . . -1.1(3) ?
    C18 C19 C20 C21 . . . . 1.9(3) ?
    O4 C19 C20 C21 . . . . -178.15(18) ?
    C18 C17 C16 C21 . . . . 1.1(3) ?
    C18 C17 C16 C15 . . . . -178.05(18) ?
    C20 C21 C16 C17 . . . . -0.4(3) ?
    C20 C21 C16 C15 . . . . 178.72(19) ?
    C14 C15 C16 C17 . . . . 177.28(19) ?
    C14 C15 C16 C21 . . . . -1.8(3) ?
    C6 C1 C2 C3 . . . . -2.7(3) ?
    S1 C1 C2 C3 . . . . 179.41(15) ?
    C8 C7 C12 C11 . . . . 2.3(3) ?
    N1 C7 C12 C11 . . . . 179.61(17) ?
    C1 C6 C5 C4 . . . . 0.2(3) ?
    C16 C15 C14 C13 . . . . 179.29(18) ?
    O3 C13 C14 C15 . . . . 4.3(3) ?
    C10 C13 C14 C15 . . . . -174.90(17) ?
    C6 C5 C4 C3 . . . . -1.8(3) ?
    C9 C10 C11 C12 . . . . 0.4(3) ?
    C13 C10 C11 C12 . . . . -179.56(17) ?
    C7 C12 C11 C10 . . . . -2.3(3) ?
    C1 C2 C3 C4 . . . . 1.1(3) ?
    C5 C4 C3 C2 . . . . 1.2(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
    _geom_hbond_publ_flag
    N1 H1 O3 4_565 0.91(3) 2.08(3) 2.987(2) 175(3) yes
    C9 H9 O1 4_566 0.93 2.34 3.228(2) 160 yes
    C23 H23A CgA 3_657 0.96 3.04 3.816(3) 138 yes
    C2 H2 O4 2_656 0.93 2.65 3.269(2) 125 yes
    C3 H3 O4 2_656 0.93 2.68 3.285(2) 124 yes
