##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-09-15
_journal_date_accepted     2010-10-01
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     11
_journal_page_first     o2757
_journal_page_last     o2758
_journal_paper_category     QO
_journal_coeditor_code     FL2319
_publ_contact_author_name     'Jasinski, Jerry P.'
_publ_contact_author_address
;
Department of Chemistry
Keene State College
229 Main Street
Keene, New Hampshire 03435, USA
;
_publ_contact_author_email     jjasinski@keene.edu
_publ_contact_author_fax     ?
_publ_contact_author_phone     '603 358-2563'
_publ_section_title
;\
4-Phenylsulfonyl-2-(p-tolylsulfonyl)-1H,8H-\
pyrrolo[2,3-b]indole
;
loop_
    _publ_author_name
    _publ_author_address
    'Badenock, Jeanese C.'
;
Department of Biological and Chemical Sciences
University of the West Indies
Cave Hill, Barbados
;
    'Jordan, Jason A.'
;
Department of Biological and Chemical Sciences
University of the West Indies
Cave Hill, Barbados
;
    'Pelkey, Erin T.'
;
Department of Chemistry
Dartmouth College
Hanover, NH 03755-3564, USA
;
    'Gribble, Gordon W.'
;
Department of Chemistry
Dartmouth College
Hanover, NH 03755-3564, USA
;
    'Jasinski, Jerry P.'
;
Department of Chemistry
Keene State College
229 Main Street
Keene, NH 03435-2001, USA
;
data_I
_chemical_name_systematic
;\
4-Phenylsulfonyl-2-(p-tolylsulfonyl)-1H,8H-
pyrrolo[2,3-b]indole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H18 N2 O4 S2'
_chemical_formula_sum     'C23 H18 N2 O4 S2'
_chemical_formula_iupac     'C23 H18 N2 O4 S2'
_chemical_formula_weight     450.51
_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_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.1547(3)
_cell_length_b     11.0471(5)
_cell_length_c     11.7185(4)
_cell_angle_alpha     73.834(4)
_cell_angle_beta     87.131(3)
_cell_angle_gamma     79.277(4)
_cell_volume     996.22(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     7126
_cell_measurement_theta_min     5.0373
_cell_measurement_theta_max     32.6945
_cell_measurement_temperature     123(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.41
_exptl_crystal_size_mid     0.36
_exptl_crystal_size_min     0.29
_exptl_crystal_density_diffrn     1.502
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     468
_exptl_absorpt_coefficient_mu     0.303
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlisRED; Oxford Diffraction, 2007)
;
_exptl_absorpt_correction_T_min     0.98084
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
;
_diffrn_ambient_temperature     123(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
        'Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini) detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     10.5081
_diffrn_reflns_number     12580
_diffrn_reflns_av_R_equivalents     0.0203
_diffrn_reflns_av_sigmaI/netI     0.0363
_diffrn_reflns_theta_min     5.05
_diffrn_reflns_theta_max     32.77
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.893
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     6592
_reflns_number_gt     5331
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0478
_refine_ls_R_factor_gt     0.0360
_refine_ls_wR_factor_gt     0.0988
_refine_ls_wR_factor_ref     0.1028
_refine_ls_goodness_of_fit_ref     1.089
_refine_ls_restrained_S_all     1.089
_refine_ls_number_reflns     6592
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0572P)²+0.0394P] 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     0.522
_refine_diff_density_min     -0.329
_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     'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_cell_refinement     'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.24124(3) 0.40940(3) 0.21069(3) 0.01455(7) Uani d . 1 . .
    S S2 0.53714(4) 0.07067(3) 0.67939(3) 0.01540(7) Uani d . 1 . .
    O O1 0.28990(11) 0.27445(8) 0.22946(8) 0.01961(18) Uani d . 1 . .
    O O2 0.10331(10) 0.48046(9) 0.13513(8) 0.01992(19) Uani d . 1 . .
    O O3 0.61740(11) -0.00088(8) 0.59944(8) 0.02005(19) Uani d . 1 . .
    O O4 0.63277(11) 0.09255(9) 0.76857(8) 0.02102(19) Uani d . 1 . .
    N N1 0.19171(12) 0.42667(9) 0.34605(9) 0.01529(19) Uani d . 1 . .
    N N2 0.36818(12) 0.22963(9) 0.48254(9) 0.01541(19) Uani d . 1 . .
    H H2B 0.3722 0.1694 0.4462 0.018 Uiso calc R 1 . .
    C C1 0.43829(15) 0.21752(11) 0.59259(10) 0.0155(2) Uani d . 1 . .
    C C2 0.40399(15) 0.33305(11) 0.62081(11) 0.0169(2) Uani d . 1 . .
    H H2A 0.4367 0.3501 0.6906 0.020 Uiso calc R 1 . .
    C C3 0.30982(15) 0.42085(11) 0.52414(11) 0.0160(2) Uani d . 1 . .
    C C4 0.21746(15) 0.55003(11) 0.47483(11) 0.0161(2) Uani d . 1 . .
    C C5 0.18616(17) 0.66151(12) 0.51200(12) 0.0218(3) Uani d . 1 . .
    H H5A 0.2306 0.6628 0.5850 0.026 Uiso calc R 1 . .
    C C6 0.08910(17) 0.77060(12) 0.44084(12) 0.0242(3) Uani d . 1 . .
    H H6A 0.0680 0.8471 0.4653 0.029 Uiso calc R 1 . .
    C C7 0.02218(16) 0.76964(12) 0.33428(12) 0.0232(3) Uani d . 1 . .
    H H7A -0.0436 0.8457 0.2871 0.028 Uiso calc R 1 . .
    C C8 0.04966(15) 0.65990(12) 0.29554(12) 0.0200(2) Uani d . 1 . .
    H H8A 0.0027 0.6588 0.2233 0.024 Uiso calc R 1 . .
    C C9 0.14851(14) 0.55177(11) 0.36653(11) 0.0159(2) Uani d . 1 . .
    C C10 0.29295(14) 0.35350(11) 0.44405(10) 0.0146(2) Uani d . 1 . .
    C C11 0.41636(14) 0.48258(11) 0.16669(10) 0.0142(2) Uani d . 1 . .
    C C12 0.57366(15) 0.40983(12) 0.20143(11) 0.0186(2) Uani d . 1 . .
    H H12A 0.5850 0.3233 0.2480 0.022 Uiso calc R 1 . .
    C C13 0.71326(15) 0.46588(13) 0.16684(12) 0.0214(3) Uani d . 1 . .
    H H13A 0.8213 0.4177 0.1901 0.026 Uiso calc R 1 . .
    C C14 0.69552(16) 0.59186(13) 0.09850(11) 0.0210(3) Uani d . 1 . .
    H H14A 0.7918 0.6295 0.0746 0.025 Uiso calc R 1 . .
    C C15 0.53830(17) 0.66374(13) 0.06448(12) 0.0214(3) Uani d . 1 . .
    H H15A 0.5276 0.7502 0.0176 0.026 Uiso calc R 1 . .
    C C16 0.39661(15) 0.60964(12) 0.09882(11) 0.0184(2) Uani d . 1 . .
    H H16A 0.2886 0.6584 0.0764 0.022 Uiso calc R 1 . .
    C C17 0.37346(15) -0.00606(11) 0.75228(10) 0.0155(2) Uani d . 1 . .
    C C18 0.34028(16) -0.00884(12) 0.87037(11) 0.0188(2) Uani d . 1 . .
    H H18A 0.4056 0.0289 0.9110 0.023 Uiso calc R 1 . .
    C C19 0.21030(16) -0.06741(12) 0.92891(11) 0.0197(2) Uani d . 1 . .
    H H19A 0.1885 -0.0706 1.0100 0.024 Uiso calc R 1 . .
    C C20 0.11216(15) -0.12121(11) 0.86952(11) 0.0175(2) Uani d . 1 . .
    C C21 0.14575(16) -0.11501(12) 0.74970(11) 0.0188(2) Uani d . 1 . .
    H H21A 0.0777 -0.1496 0.7080 0.023 Uiso calc R 1 . .
    C C22 0.27672(15) -0.05922(11) 0.69078(11) 0.0178(2) Uani d . 1 . .
    H H22A 0.3001 -0.0573 0.6101 0.021 Uiso calc R 1 . .
    C C23 -0.02767(17) -0.18520(13) 0.93246(13) 0.0244(3) Uani d . 1 . .
    H H23A -0.0415 -0.1727 1.0122 0.037 Uiso calc R 1 . .
    H H23B -0.0010 -0.2771 0.9388 0.037 Uiso calc R 1 . .
    H H23C -0.1315 -0.1475 0.8873 0.037 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O1 . 1.4263(9) ?
    S1 O2 . 1.4316(9) ?
    S1 N1 . 1.6707(10) ?
    S1 C11 . 1.7557(12) ?
    S2 O4 . 1.4322(9) ?
    S2 O3 . 1.4455(9) ?
    S2 C1 . 1.7300(12) ?
    S2 C17 . 1.7701(12) ?
    N1 C10 . 1.4084(15) ?
    N1 C9 . 1.4446(15) ?
    N2 C10 . 1.3506(14) ?
    N2 C1 . 1.3990(15) ?
    N2 H2B . 0.8800 ?
    C1 C2 . 1.3818(17) ?
    C2 C3 . 1.4184(17) ?
    C2 H2A . 0.9500 ?
    C3 C10 . 1.3760(17) ?
    C3 C4 . 1.4567(16) ?
    C4 C5 . 1.3937(18) ?
    C4 C9 . 1.4075(17) ?
    C5 C6 . 1.3877(18) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.391(2) ?
    C6 H6A . 0.9500 ?
    C7 C8 . 1.3861(19) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.3871(16) ?
    C8 H8A . 0.9500 ?
    C11 C16 . 1.3914(16) ?
    C11 C12 . 1.3941(16) ?
    C12 C13 . 1.3856(18) ?
    C12 H12A . 0.9500 ?
    C13 C14 . 1.3839(19) ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.3889(18) ?
    C14 H14A . 0.9500 ?
    C15 C16 . 1.3895(18) ?
    C15 H15A . 0.9500 ?
    C16 H16A . 0.9500 ?
    C17 C18 . 1.3896(17) ?
    C17 C22 . 1.3970(17) ?
    C18 C19 . 1.3958(17) ?
    C18 H18A . 0.9500 ?
    C19 C20 . 1.3932(18) ?
    C19 H19A . 0.9500 ?
    C20 C21 . 1.4022(17) ?
    C20 C23 . 1.5065(17) ?
    C21 C22 . 1.3897(17) ?
    C21 H21A . 0.9500 ?
    C22 H22A . 0.9500 ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 S1 O2 . . 121.13(6) ?
    O1 S1 N1 . . 104.32(5) ?
    O2 S1 N1 . . 106.30(5) ?
    O1 S1 C11 . . 109.10(5) ?
    O2 S1 C11 . . 109.09(5) ?
    N1 S1 C11 . . 105.77(5) ?
    O4 S2 O3 . . 120.17(6) ?
    O4 S2 C1 . . 108.32(6) ?
    O3 S2 C1 . . 107.11(6) ?
    O4 S2 C17 . . 107.49(6) ?
    O3 S2 C17 . . 107.91(6) ?
    C1 S2 C17 . . 104.84(6) ?
    C10 N1 C9 . . 103.92(10) ?
    C10 N1 S1 . . 119.83(8) ?
    C9 N1 S1 . . 121.49(8) ?
    C10 N2 C1 . . 105.31(10) ?
    C10 N2 H2B . . 127.3 ?
    C1 N2 H2B . . 127.3 ?
    C2 C1 N2 . . 110.47(10) ?
    C2 C1 S2 . . 128.02(10) ?
    N2 C1 S2 . . 121.31(9) ?
    C1 C2 C3 . . 105.85(11) ?
    C1 C2 H2A . . 127.1 ?
    C3 C2 H2A . . 127.1 ?
    C10 C3 C2 . . 106.48(10) ?
    C10 C3 C4 . . 106.28(10) ?
    C2 C3 C4 . . 147.16(12) ?
    C5 C4 C9 . . 118.78(11) ?
    C5 C4 C3 . . 134.52(12) ?
    C9 C4 C3 . . 106.70(10) ?
    C6 C5 C4 . . 119.01(13) ?
    C6 C5 H5A . . 120.5 ?
    C4 C5 H5A . . 120.5 ?
    C5 C6 C7 . . 121.04(12) ?
    C5 C6 H6A . . 119.5 ?
    C7 C6 H6A . . 119.5 ?
    C8 C7 C6 . . 121.29(12) ?
    C8 C7 H7A . . 119.4 ?
    C6 C7 H7A . . 119.4 ?
    C7 C8 C9 . . 117.26(12) ?
    C7 C8 H8A . . 121.4 ?
    C9 C8 H8A . . 121.4 ?
    C8 C9 C4 . . 122.62(11) ?
    C8 C9 N1 . . 127.30(11) ?
    C4 C9 N1 . . 110.05(10) ?
    N2 C10 C3 . . 111.89(11) ?
    N2 C10 N1 . . 134.91(11) ?
    C3 C10 N1 . . 112.99(10) ?
    C16 C11 C12 . . 121.61(11) ?
    C16 C11 S1 . . 120.24(9) ?
    C12 C11 S1 . . 118.15(9) ?
    C13 C12 C11 . . 118.89(11) ?
    C13 C12 H12A . . 120.6 ?
    C11 C12 H12A . . 120.6 ?
    C14 C13 C12 . . 120.11(12) ?
    C14 C13 H13A . . 119.9 ?
    C12 C13 H13A . . 119.9 ?
    C13 C14 C15 . . 120.63(12) ?
    C13 C14 H14A . . 119.7 ?
    C15 C14 H14A . . 119.7 ?
    C14 C15 C16 . . 120.20(12) ?
    C14 C15 H15A . . 119.9 ?
    C16 C15 H15A . . 119.9 ?
    C15 C16 C11 . . 118.56(11) ?
    C15 C16 H16A . . 120.7 ?
    C11 C16 H16A . . 120.7 ?
    C18 C17 C22 . . 120.89(11) ?
    C18 C17 S2 . . 118.71(10) ?
    C22 C17 S2 . . 120.37(9) ?
    C17 C18 C19 . . 119.56(12) ?
    C17 C18 H18A . . 120.2 ?
    C19 C18 H18A . . 120.2 ?
    C20 C19 C18 . . 120.61(12) ?
    C20 C19 H19A . . 119.7 ?
    C18 C19 H19A . . 119.7 ?
    C19 C20 C21 . . 118.85(11) ?
    C19 C20 C23 . . 120.83(11) ?
    C21 C20 C23 . . 120.31(12) ?
    C22 C21 C20 . . 121.23(12) ?
    C22 C21 H21A . . 119.4 ?
    C20 C21 H21A . . 119.4 ?
    C21 C22 C17 . . 118.83(11) ?
    C21 C22 H22A . . 120.6 ?
    C17 C22 H22A . . 120.6 ?
    C20 C23 H23A . . 109.5 ?
    C20 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C20 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
    O1 S1 N1 C10 . . . . 42.28(10) ?
    O2 S1 N1 C10 . . . . 171.37(9) ?
    C11 S1 N1 C10 . . . . -72.74(10) ?
    O1 S1 N1 C9 . . . . 174.84(9) ?
    O2 S1 N1 C9 . . . . -56.07(10) ?
    C11 S1 N1 C9 . . . . 59.82(10) ?
    C10 N2 C1 C2 . . . . 0.64(13) ?
    C10 N2 C1 S2 . . . . 175.91(9) ?
    O4 S2 C1 C2 . . . . -20.80(13) ?
    O3 S2 C1 C2 . . . . -151.78(11) ?
    C17 S2 C1 C2 . . . . 93.73(12) ?
    O4 S2 C1 N2 . . . . 164.83(9) ?
    O3 S2 C1 N2 . . . . 33.85(11) ?
    C17 S2 C1 N2 . . . . -80.63(10) ?
    N2 C1 C2 C3 . . . . -0.43(14) ?
    S2 C1 C2 C3 . . . . -175.30(9) ?
    C1 C2 C3 C10 . . . . 0.05(13) ?
    C1 C2 C3 C4 . . . . 176.14(18) ?
    C10 C3 C4 C5 . . . . 179.76(14) ?
    C2 C3 C4 C5 . . . . 3.7(3) ?
    C10 C3 C4 C9 . . . . 0.47(13) ?
    C2 C3 C4 C9 . . . . -175.62(18) ?
    C9 C4 C5 C6 . . . . -0.39(18) ?
    C3 C4 C5 C6 . . . . -179.62(13) ?
    C4 C5 C6 C7 . . . . 0.5(2) ?
    C5 C6 C7 C8 . . . . 0.1(2) ?
    C6 C7 C8 C9 . . . . -0.90(19) ?
    C7 C8 C9 C4 . . . . 1.05(18) ?
    C7 C8 C9 N1 . . . . 178.71(12) ?
    C5 C4 C9 C8 . . . . -0.41(18) ?
    C3 C4 C9 C8 . . . . 179.01(11) ?
    C5 C4 C9 N1 . . . . -178.44(11) ?
    C3 C4 C9 N1 . . . . 0.99(13) ?
    C10 N1 C9 C8 . . . . -179.91(11) ?
    S1 N1 C9 C8 . . . . 41.26(16) ?
    C10 N1 C9 C4 . . . . -2.01(12) ?
    S1 N1 C9 C4 . . . . -140.84(9) ?
    C1 N2 C10 C3 . . . . -0.61(13) ?
    C1 N2 C10 N1 . . . . -174.88(12) ?
    C2 C3 C10 N2 . . . . 0.36(14) ?
    C4 C3 C10 N2 . . . . -177.43(10) ?
    C2 C3 C10 N1 . . . . 175.95(10) ?
    C4 C3 C10 N1 . . . . -1.84(13) ?
    C9 N1 C10 N2 . . . . 176.61(13) ?
    S1 N1 C10 N2 . . . . -43.72(18) ?
    C9 N1 C10 C3 . . . . 2.39(13) ?
    S1 N1 C10 C3 . . . . 142.06(9) ?
    O1 S1 C11 C16 . . . . 154.12(10) ?
    O2 S1 C11 C16 . . . . 19.79(12) ?
    N1 S1 C11 C16 . . . . -94.18(11) ?
    O1 S1 C11 C12 . . . . -25.73(11) ?
    O2 S1 C11 C12 . . . . -160.07(10) ?
    N1 S1 C11 C12 . . . . 85.96(11) ?
    C16 C11 C12 C13 . . . . -0.25(19) ?
    S1 C11 C12 C13 . . . . 179.61(10) ?
    C11 C12 C13 C14 . . . . -0.3(2) ?
    C12 C13 C14 C15 . . . . 0.4(2) ?
    C13 C14 C15 C16 . . . . 0.0(2) ?
    C14 C15 C16 C11 . . . . -0.49(19) ?
    C12 C11 C16 C15 . . . . 0.64(19) ?
    S1 C11 C16 C15 . . . . -179.22(10) ?
    O4 S2 C17 C18 . . . . 12.96(11) ?
    O3 S2 C17 C18 . . . . 143.93(9) ?
    C1 S2 C17 C18 . . . . -102.15(10) ?
    O4 S2 C17 C22 . . . . -168.94(9) ?
    O3 S2 C17 C22 . . . . -37.97(11) ?
    C1 S2 C17 C22 . . . . 75.95(11) ?
    C22 C17 C18 C19 . . . . 1.07(17) ?
    S2 C17 C18 C19 . . . . 179.16(9) ?
    C17 C18 C19 C20 . . . . -1.00(18) ?
    C18 C19 C20 C21 . . . . -0.28(18) ?
    C18 C19 C20 C23 . . . . 179.65(11) ?
    C19 C20 C21 C22 . . . . 1.53(18) ?
    C23 C20 C21 C22 . . . . -178.40(11) ?
    C20 C21 C22 C17 . . . . -1.47(18) ?
    C18 C17 C22 C21 . . . . 0.15(17) ?
    S2 C17 C22 C21 . . . . -177.91(9) ?
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
    N2 H2B O3 2_656 0.88 2.06 2.9244(14) 166.7
    C13 H13A O2 1_655 0.95 2.53 3.2125(15) 129.3
    C22 H22A O3 2_656 0.95 2.45 3.3786(15) 165.0
