##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# 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.                                        #
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##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2012-03-08
_journal_date_accepted     2012-03-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      4
_journal_page_first     o1086
_journal_page_last     o1087
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812010598
_journal_coeditor_code     HB6674
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
edward.tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 6775 '
_publ_section_title
;
1-(4-Methylphenyl)-3-phenyl-1H-pyrazol-5-yl 4-nitrobenzenesulfonate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Solange M. S. V. Wardell' .
;
CHEMSOL, 1 Harcourt Road, Aberdeen, AB15 5NY, Scotland
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Wardell, James L.'
;
Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.
;
;
Centro de Desenvolvimento Tecnológico em Saúde (CDTS),
Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela,
Campus de Manguinhos, Av. Brasil 4365,
21040-900 Rio de Janeiro, RJ, Brazil
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-(4-Methylphenyl)-3-phenyl-1H-pyrazol-5-yl 4-nitrobenzenesulfonate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H17 N3 O5 S'
_chemical_formula_sum     'C22 H17 N3 O5 S'
_chemical_formula_iupac     'C22 H17 N3 O5 S'
_chemical_formula_weight     435.46
_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     13.5339(12)
_cell_length_b     10.4827(10)
_cell_length_c     14.9303(13)
_cell_angle_alpha     90.00
_cell_angle_beta     111.975(3)
_cell_angle_gamma     90.00
_cell_volume     1964.3(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     67707
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.58
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.472
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     904
_exptl_absorpt_coefficient_mu     0.207
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min     0.6199
_exptl_absorpt_correction_T_max     0.7456
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'Confocal'
_diffrn_measurement_device_type
;
Rigaku Saturn724+
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_method     'profile data from ω-scans'
_diffrn_detector_area_resol_mean     28.5714
_diffrn_reflns_number     4454
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0172
_diffrn_reflns_theta_min     3.22
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     19
_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 >
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     4454
_reflns_number_gt     3951
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0796
_refine_ls_R_factor_gt     0.0686
_refine_ls_wR_factor_gt     0.1698
_refine_ls_wR_factor_ref     0.1788
_refine_ls_goodness_of_fit_ref     1.191
_refine_ls_restrained_S_all     1.191
_refine_ls_number_reflns     4454
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0562P)²+4.7370P] 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     0.590
_refine_diff_density_min     -0.622
_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'
    '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     'COLLECT (Hooft, 1998)'
_computing_cell_refinement
                    'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction
                    'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                      'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.47829(6) 0.20331(9) 0.00726(6) 0.0203(2) Uani d . 1 1 . .
    O O1 0.51909(18) 0.3508(3) 0.01445(17) 0.0203(5) Uani d . 1 1 . .
    O O2 0.5619(2) 0.1219(3) 0.0044(2) 0.0268(6) Uani d . 1 1 . .
    O O3 0.4369(2) 0.1938(3) 0.08223(19) 0.0315(7) Uani d . 1 1 . .
    O O4 0.1490(2) 0.2303(3) -0.4513(2) 0.0360(7) Uani d . 1 1 . .
    O O5 0.0359(2) 0.2650(3) -0.3824(2) 0.0377(8) Uani d . 1 1 . .
    N N1 0.7023(2) 0.4081(3) 0.0618(2) 0.0156(6) Uani d . 1 1 . .
    N N2 0.7780(2) 0.4243(3) 0.0225(2) 0.0156(6) Uani d . 1 1 . .
    N N3 0.1265(2) 0.2427(3) -0.3796(2) 0.0254(7) Uani d . 1 1 . .
    C C1 0.6074(2) 0.3760(3) -0.0095(2) 0.0169(7) Uani d . 1 1 . .
    C C2 0.7290(2) 0.4006(3) -0.0717(2) 0.0141(6) Uani d . 1 1 . .
    C C3 0.6198(3) 0.3718(3) -0.0957(2) 0.0183(7) Uani d . 1 1 . .
    H H3 0.5673 0.3539 -0.1576 0.022 Uiso calc R 1 1 . .
    C C4 0.3726(3) 0.2062(3) -0.1065(3) 0.0185(7) Uani d . 1 1 . .
    C C5 0.2715(3) 0.2430(4) -0.1110(3) 0.0206(7) Uani d . 1 1 . .
    H H5 0.2587 0.2609 -0.0539 0.025 Uiso calc R 1 1 . .
    C C6 0.1898(3) 0.2525(4) -0.2022(3) 0.0222(7) Uani d . 1 1 . .
    H H6 0.1196 0.2749 -0.2081 0.027 Uiso calc R 1 1 . .
    C C7 0.2126(3) 0.2292(3) -0.2831(3) 0.0199(7) Uani d . 1 1 . .
    C C8 0.3132(3) 0.1929(4) -0.2796(3) 0.0220(7) Uani d . 1 1 . .
    H H8 0.3262 0.1777 -0.3370 0.026 Uiso calc R 1 1 . .
    C C9 0.3942(3) 0.1796(3) -0.1886(3) 0.0189(7) Uani d . 1 1 . .
    H H9 0.4633 0.1527 -0.1829 0.023 Uiso calc R 1 1 . .
    C C10 0.7302(3) 0.4228(3) 0.1639(2) 0.0152(6) Uani d . 1 1 . .
    C C11 0.8359(3) 0.3992(3) 0.2245(3) 0.0181(7) Uani d . 1 1 . .
    H H11 0.8871 0.3757 0.1980 0.022 Uiso calc R 1 1 . .
    C C12 0.8651(3) 0.4106(3) 0.3239(2) 0.0198(7) Uani d . 1 1 . .
    H H12 0.9369 0.3951 0.3651 0.024 Uiso calc R 1 1 . .
    C C13 0.7909(3) 0.4445(3) 0.3644(3) 0.0210(7) Uani d . 1 1 . .
    C C14 0.6856(3) 0.4686(4) 0.3023(3) 0.0211(7) Uani d . 1 1 . .
    H H14 0.6343 0.4919 0.3287 0.025 Uiso calc R 1 1 . .
    C C15 0.6551(3) 0.4590(3) 0.2020(3) 0.0197(7) Uani d . 1 1 . .
    H H15 0.5838 0.4770 0.1604 0.024 Uiso calc R 1 1 . .
    C C16 0.8218(3) 0.4510(4) 0.4733(3) 0.0307(9) Uani d . 1 1 . .
    H H16A 0.7642 0.4912 0.4879 0.046 Uiso calc R 1 1 . .
    H H16B 0.8871 0.5014 0.5020 0.046 Uiso calc R 1 1 . .
    H H16C 0.8341 0.3645 0.5002 0.046 Uiso calc R 1 1 . .
    C C17 0.7883(3) 0.4054(3) -0.1369(2) 0.0157(6) Uani d . 1 1 . .
    C C18 0.7359(3) 0.3973(3) -0.2370(2) 0.0166(6) Uani d . 1 1 . .
    H H18 0.6609 0.3851 -0.2640 0.020 Uiso calc R 1 1 . .
    C C19 0.7925(3) 0.4068(3) -0.2978(2) 0.0191(7) Uani d . 1 1 . .
    H H19 0.7563 0.4007 -0.3658 0.023 Uiso calc R 1 1 . .
    C C20 0.9031(3) 0.4255(4) -0.2584(3) 0.0210(7) Uani d . 1 1 . .
    H H20 0.9417 0.4348 -0.2997 0.025 Uiso calc R 1 1 . .
    C C21 0.9563(3) 0.4303(3) -0.1586(3) 0.0194(7) Uani d . 1 1 . .
    H H21 1.0315 0.4409 -0.1319 0.023 Uiso calc R 1 1 . .
    C C22 0.8997(3) 0.4196(3) -0.0977(2) 0.0185(7) Uani d . 1 1 . .
    H H22 0.9365 0.4218 -0.0297 0.022 Uiso calc R 1 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 O3 . 1.430(3) ?
    S1 O2 . 1.431(3) ?
    S1 O1 . 1.632(3) ?
    S1 C4 . 1.765(3) ?
    O1 C1 . 1.395(4) ?
    O4 N3 . 1.225(4) ?
    O5 N3 . 1.233(4) ?
    N1 N2 . 1.366(4) ?
    N1 C1 . 1.368(4) ?
    N1 C10 . 1.435(4) ?
    N2 C2 . 1.336(4) ?
    N3 C7 . 1.482(5) ?
    C1 C3 . 1.360(5) ?
    C2 C3 . 1.417(4) ?
    C2 C17 . 1.476(4) ?
    C3 H3 . 0.9500 ?
    C4 C9 . 1.390(5) ?
    C4 C5 . 1.399(5) ?
    C5 C6 . 1.399(5) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.376(5) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.396(5) ?
    C8 C9 . 1.397(5) ?
    C8 H8 . 0.9500 ?
    C9 H9 . 0.9500 ?
    C10 C15 . 1.391(5) ?
    C10 C11 . 1.399(4) ?
    C11 C12 . 1.391(5) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.397(5) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.402(5) ?
    C13 C16 . 1.522(5) ?
    C14 C15 . 1.401(5) ?
    C14 H14 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 C18 . 1.397(5) ?
    C17 C22 . 1.406(5) ?
    C18 C19 . 1.393(5) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.402(5) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.391(5) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.396(5) ?
    C21 H21 . 0.9500 ?
    C22 H22 . 0.9500 ?
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
    O3 S1 O2 . . 121.83(18) ?
    O3 S1 O1 . . 103.66(16) ?
    O2 S1 O1 . . 108.38(14) ?
    O3 S1 C4 . . 109.94(16) ?
    O2 S1 C4 . . 110.29(17) ?
    O1 S1 C4 . . 100.35(15) ?
    C1 O1 S1 . . 117.6(2) ?
    N2 N1 C1 . . 109.5(3) ?
    N2 N1 C10 . . 120.0(3) ?
    C1 N1 C10 . . 130.5(3) ?
    C2 N2 N1 . . 105.8(2) ?
    O4 N3 O5 . . 124.0(3) ?
    O4 N3 C7 . . 118.5(3) ?
    O5 N3 C7 . . 117.4(3) ?
    C3 C1 N1 . . 109.4(3) ?
    C3 C1 O1 . . 131.1(3) ?
    N1 C1 O1 . . 119.5(3) ?
    N2 C2 C3 . . 111.4(3) ?
    N2 C2 C17 . . 120.7(3) ?
    C3 C2 C17 . . 127.9(3) ?
    C1 C3 C2 . . 103.9(3) ?
    C1 C3 H3 . . 128.0 ?
    C2 C3 H3 . . 128.0 ?
    C9 C4 C5 . . 122.5(3) ?
    C9 C4 S1 . . 118.9(3) ?
    C5 C4 S1 . . 118.5(3) ?
    C4 C5 C6 . . 118.0(3) ?
    C4 C5 H5 . . 121.0 ?
    C6 C5 H5 . . 121.0 ?
    C7 C6 C5 . . 119.1(3) ?
    C7 C6 H6 . . 120.4 ?
    C5 C6 H6 . . 120.4 ?
    C6 C7 C8 . . 123.5(3) ?
    C6 C7 N3 . . 118.9(3) ?
    C8 C7 N3 . . 117.6(3) ?
    C7 C8 C9 . . 117.5(3) ?
    C7 C8 H8 . . 121.2 ?
    C9 C8 H8 . . 121.2 ?
    C4 C9 C8 . . 119.4(3) ?
    C4 C9 H9 . . 120.3 ?
    C8 C9 H9 . . 120.3 ?
    C15 C10 C11 . . 120.7(3) ?
    C15 C10 N1 . . 121.5(3) ?
    C11 C10 N1 . . 117.8(3) ?
    C12 C11 C10 . . 119.2(3) ?
    C12 C11 H11 . . 120.4 ?
    C10 C11 H11 . . 120.4 ?
    C11 C12 C13 . . 121.4(3) ?
    C11 C12 H12 . . 119.3 ?
    C13 C12 H12 . . 119.3 ?
    C12 C13 C14 . . 118.5(3) ?
    C12 C13 C16 . . 121.3(3) ?
    C14 C13 C16 . . 120.2(3) ?
    C15 C14 C13 . . 120.9(3) ?
    C15 C14 H14 . . 119.5 ?
    C13 C14 H14 . . 119.5 ?
    C10 C15 C14 . . 119.2(3) ?
    C10 C15 H15 . . 120.4 ?
    C14 C15 H15 . . 120.4 ?
    C13 C16 H16A . . 109.5 ?
    C13 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C13 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C18 C17 C22 . . 119.2(3) ?
    C18 C17 C2 . . 121.3(3) ?
    C22 C17 C2 . . 119.5(3) ?
    C19 C18 C17 . . 120.7(3) ?
    C19 C18 H18 . . 119.7 ?
    C17 C18 H18 . . 119.7 ?
    C18 C19 C20 . . 119.8(3) ?
    C18 C19 H19 . . 120.1 ?
    C20 C19 H19 . . 120.1 ?
    C21 C20 C19 . . 119.9(3) ?
    C21 C20 H20 . . 120.1 ?
    C19 C20 H20 . . 120.1 ?
    C20 C21 C22 . . 120.3(3) ?
    C20 C21 H21 . . 119.9 ?
    C22 C21 H21 . . 119.9 ?
    C21 C22 C17 . . 120.1(3) ?
    C21 C22 H22 . . 119.9 ?
    C17 C22 H22 . . 119.9 ?
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 O1 C1 . . . . 147.7(2) ?
    O2 S1 O1 C1 . . . . 17.0(3) ?
    C4 S1 O1 C1 . . . . -98.6(2) ?
    C1 N1 N2 C2 . . . . -0.7(4) ?
    C10 N1 N2 C2 . . . . 178.1(3) ?
    N2 N1 C1 C3 . . . . -0.5(4) ?
    C10 N1 C1 C3 . . . . -179.1(3) ?
    N2 N1 C1 O1 . . . . 178.0(3) ?
    C10 N1 C1 O1 . . . . -0.5(6) ?
    S1 O1 C1 C3 . . . . 69.1(5) ?
    S1 O1 C1 N1 . . . . -109.1(3) ?
    N1 N2 C2 C3 . . . . 1.5(4) ?
    N1 N2 C2 C17 . . . . -178.1(3) ?
    N1 C1 C3 C2 . . . . 1.3(4) ?
    O1 C1 C3 C2 . . . . -177.0(4) ?
    N2 C2 C3 C1 . . . . -1.8(4) ?
    C17 C2 C3 C1 . . . . 177.8(3) ?
    O3 S1 C4 C9 . . . . -162.3(3) ?
    O2 S1 C4 C9 . . . . -25.3(3) ?
    O1 S1 C4 C9 . . . . 88.9(3) ?
    O3 S1 C4 C5 . . . . 21.6(4) ?
    O2 S1 C4 C5 . . . . 158.7(3) ?
    O1 S1 C4 C5 . . . . -87.2(3) ?
    C9 C4 C5 C6 . . . . 0.2(5) ?
    S1 C4 C5 C6 . . . . 176.1(3) ?
    C4 C5 C6 C7 . . . . -1.8(5) ?
    C5 C6 C7 C8 . . . . 1.6(6) ?
    C5 C6 C7 N3 . . . . -178.4(3) ?
    O4 N3 C7 C6 . . . . 175.1(4) ?
    O5 N3 C7 C6 . . . . -5.4(5) ?
    O4 N3 C7 C8 . . . . -5.0(5) ?
    O5 N3 C7 C8 . . . . 174.5(4) ?
    C6 C7 C8 C9 . . . . 0.2(6) ?
    N3 C7 C8 C9 . . . . -179.7(3) ?
    C5 C4 C9 C8 . . . . 1.7(5) ?
    S1 C4 C9 C8 . . . . -174.2(3) ?
    C7 C8 C9 C4 . . . . -1.8(5) ?
    N2 N1 C10 C15 . . . . 153.3(3) ?
    C1 N1 C10 C15 . . . . -28.3(6) ?
    N2 N1 C10 C11 . . . . -26.9(5) ?
    C1 N1 C10 C11 . . . . 151.6(4) ?
    C15 C10 C11 C12 . . . . 0.9(5) ?
    N1 C10 C11 C12 . . . . -179.0(3) ?
    C10 C11 C12 C13 . . . . 0.4(5) ?
    C11 C12 C13 C14 . . . . -0.8(5) ?
    C11 C12 C13 C16 . . . . 177.2(4) ?
    C12 C13 C14 C15 . . . . 0.1(5) ?
    C16 C13 C14 C15 . . . . -177.9(4) ?
    C11 C10 C15 C14 . . . . -1.6(5) ?
    N1 C10 C15 C14 . . . . 178.2(3) ?
    C13 C14 C15 C10 . . . . 1.1(5) ?
    N2 C2 C17 C18 . . . . -171.6(3) ?
    C3 C2 C17 C18 . . . . 8.8(5) ?
    N2 C2 C17 C22 . . . . 7.8(5) ?
    C3 C2 C17 C22 . . . . -171.8(3) ?
    C22 C17 C18 C19 . . . . -1.9(5) ?
    C2 C17 C18 C19 . . . . 177.5(3) ?
    C17 C18 C19 C20 . . . . -0.4(5) ?
    C18 C19 C20 C21 . . . . 2.1(6) ?
    C19 C20 C21 C22 . . . . -1.5(6) ?
    C20 C21 C22 C17 . . . . -0.8(5) ?
    C18 C17 C22 C21 . . . . 2.5(5) ?
    C2 C17 C22 C21 . . . . -177.0(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
    C5 H5 O4 4_566 0.95 2.50 3.387(5) 155
