##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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     2005-07-07
_journal_date_accepted     2005-07-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      8
_journal_page_first     o2730
_journal_page_last     o2732
_journal_paper_category     EO
_journal_coeditor_code     OB6551
_publ_contact_author_name     'Professor. Wenjing Xiao'
_publ_contact_author_address
; Key Laboratory of Pesticide & Chemical Biology
  Ministry of Education
  College of Chemistry
  Central China Normal University
  Wuhan  430079
  P. R. China
;
_publ_contact_author_email     wxiao@mail.ccnu.edu.cn
_publ_contact_author_fax     '86 27 67862041'
_publ_contact_author_phone     '86 27 67862041'
_publ_section_title
;\
(1R,2R,2'S)-2-(4-Methylphenylsulfonamido)-1-(pyrrolidine-\
2'- carboxamido)cyclohexane
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Xinyong Li' .
;
Key Laboratory of Pesticides & Chemical Biology
Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Jiarong Chen' .
;
Key Laboratory of Pesticides & Chemical Biology
Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Xianggao Meng' .
;
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Wenjing Xiao' .
;
Key Laboratory of Pesticides & Chemical Biology
Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(1R,2R,2'S)-2-(4-Methylphenylsulfonamido)-1-(pyrrolidine-2'-
carboxamido)cyclohexane
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H27 N3 O3 S'
_chemical_formula_sum     'C18 H27 N3 O3 S'
_chemical_formula_iupac     'C18 H27 N3 O3 S'
_chemical_formula_weight     365.49
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_HalL     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     9.8855(7)
_cell_length_b     9.8856(7)
_cell_length_c     20.3477(14)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1988.5(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1748
_cell_measurement_theta_min     2.29
_cell_measurement_theta_max     19.58
_cell_measurement_temperature     292(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.221
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     784
_exptl_absorpt_coefficient_mu     0.183
_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     292(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     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10678
_diffrn_reflns_av_R_equivalents     0.0856
_diffrn_reflns_av_sigmaI/netI     0.0818
_diffrn_reflns_theta_min     2.00
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     23
_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 > 2sigma(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     3506
_reflns_number_gt     2489
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0829
_refine_ls_R_factor_gt     0.0562
_refine_ls_wR_factor_gt     0.0891
_refine_ls_wR_factor_ref     0.1006
_refine_ls_goodness_of_fit_ref     0.945
_refine_ls_restrained_S_all     0.945
_refine_ls_number_reflns     3506
_refine_ls_number_parameters     242
_refine_ls_number_restraints     9
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'calc w = 1/[σ²(Fo²)+(0.035P)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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.148
_refine_diff_density_min     -0.209
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1482 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.08(10)
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     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT-Plus (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2001)'
_computing_publication_material     'SHELXTL'
loop_
    _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
    _atom_site_type_symbol
    C1 0.2764(4) 0.6821(5) 0.36451(19) 0.0941(14) Uani d . 1 . . C
    H1A 0.2413 0.7726 0.3657 0.141 Uiso calc R 1 . . H
    H1B 0.3529 0.6754 0.3934 0.141 Uiso calc R 1 . . H
    H1C 0.2076 0.6199 0.3784 0.141 Uiso calc R 1 . . H
    C2 0.3193(4) 0.6484(4) 0.29582(18) 0.0642(10) Uani d . 1 . . C
    C3 0.4218(4) 0.5570(4) 0.28353(18) 0.0660(10) Uani d . 1 . . C
    H3 0.4677 0.5189 0.3189 0.079 Uiso calc R 1 . . H
    C4 0.4585(3) 0.5201(3) 0.22073(18) 0.0597(9) Uani d . 1 . . C
    H4 0.5258 0.4559 0.2141 0.072 Uiso calc R 1 . . H
    C5 0.3940(3) 0.5796(3) 0.16758(17) 0.0533(9) Uani d . 1 . . C
    C6 0.2961(4) 0.6759(4) 0.17824(19) 0.0725(11) Uani d . 1 . . C
    H6 0.2546 0.7188 0.1429 0.087 Uiso calc R 1 . . H
    C7 0.2597(4) 0.7085(4) 0.2421(2) 0.0836(12) Uani d . 1 . . C
    H7 0.1927 0.7731 0.2489 0.100 Uiso calc R 1 . . H
    C8 0.6864(3) 0.6570(3) 0.09824(15) 0.0457(8) Uani d . 1 . . C
    H8 0.6910 0.5794 0.1281 0.055 Uiso calc R 1 . . H
    C9 0.7014(3) 0.7842(3) 0.13860(16) 0.0607(10) Uani d . 1 . . C
    H9A 0.6321 0.7852 0.1723 0.073 Uiso calc R 1 . . H
    H9B 0.6869 0.8620 0.1105 0.073 Uiso calc R 1 . . H
    C10 0.8391(4) 0.7965(4) 0.17102(18) 0.0744(11) Uani d . 1 . . C
    H10A 0.8454 0.8824 0.1938 0.089 Uiso calc R 1 . . H
    H10B 0.8503 0.7247 0.2030 0.089 Uiso calc R 1 . . H
    C11 0.9499(4) 0.7873(4) 0.11966(19) 0.0741(11) Uani d . 1 . . C
    H11A 1.0377 0.7922 0.1408 0.089 Uiso calc R 1 . . H
    H11B 0.9425 0.8625 0.0893 0.089 Uiso calc R 1 . . H
    C12 0.9374(3) 0.6539(3) 0.08221(17) 0.0631(9) Uani d . 1 . . C
    H12A 1.0086 0.6482 0.0495 0.076 Uiso calc R 1 . . H
    H12B 0.9483 0.5789 0.1125 0.076 Uiso calc R 1 . . H
    C13 0.7998(3) 0.6433(3) 0.04839(15) 0.0447(8) Uani d . 1 . . C
    H13 0.7922 0.7185 0.0172 0.054 Uiso calc R 1 . . H
    C14 0.8428(3) 0.4959(3) -0.04649(15) 0.0455(8) Uani d . 1 . . C
    C15 0.8157(4) 0.3594(3) -0.07665(16) 0.0534(9) Uani d . 1 B . C
    H15 0.9025 0.3151 -0.0855 0.064 Uiso calc R 1 . . H
    C16 0.7380(5) 0.3716(4) -0.14104(19) 0.0876(13) Uani d D 1 . . C
    H16A 0.7002 0.4617 -0.1456 0.105 Uiso calc PR 0.80 A 1 H
    H16B 0.7973 0.3544 -0.1781 0.105 Uiso calc PR 0.80 A 1 H
    H16C 0.7513 0.4614 -0.1612 0.105 Uiso d PR 0.20 A 2 H
    H16D 0.7605 0.3029 -0.1718 0.105 Uiso d PR 0.20 A 2 H
    C17' 0.5984(12) 0.3564(19) -0.1159(10) 0.118(3) Uani d PD 0.20 B 2 C
    H17D 0.5364 0.3334 -0.1510 0.141 Uiso calc PR 0.20 B 2 H
    H17C 0.5678 0.4390 -0.0949 0.141 Uiso calc PR 0.20 B 2 H
    C17 0.6275(6) 0.2683(8) -0.1385(2) 0.118(3) Uani d PD 0.80 B 1 C
    H17B 0.5452 0.3028 -0.1582 0.141 Uiso calc PR 0.80 B 1 H
    H17A 0.6541 0.1860 -0.1610 0.141 Uiso calc PR 0.80 B 1 H
    C18 0.6089(5) 0.2439(6) -0.0673(2) 0.1091(16) Uani d D 1 . . C
    H18A 0.5383 0.3023 -0.0502 0.131 Uiso calc PR 0.80 B 1 H
    H18B 0.5823 0.1507 -0.0598 0.131 Uiso calc PR 0.80 B 1 H
    H18C 0.5327 0.2500 -0.0354 0.131 Uiso d PR 0.20 B 2 H
    H18D 0.6076 0.1593 -0.0879 0.131 Uiso d PR 0.20 B 2 H
    N1 0.5526(3) 0.6551(3) 0.06538(12) 0.0501(7) Uani d D 1 . . N
    N2 0.7870(3) 0.5183(3) 0.01187(13) 0.0487(7) Uani d D 1 . . N
    N3 0.7354(4) 0.2718(3) -0.03412(16) 0.0646(8) Uani d D 1 B . N
    O1 0.3284(2) 0.5597(2) 0.04482(11) 0.0671(7) Uani d . 1 . . O
    O2 0.5118(2) 0.4153(2) 0.08754(13) 0.0731(7) Uani d . 1 . . O
    O3 0.9126(2) 0.5808(2) -0.07526(11) 0.0663(7) Uani d . 1 . . O
    S1 0.44327(9) 0.54259(8) 0.08667(4) 0.0544(2) Uani d . 1 . . S
    H3A 0.779(3) 0.198(2) -0.0283(17) 0.068(13) Uiso d D 1 . . H
    H1 0.517(3) 0.7322(16) 0.0598(13) 0.044(10) Uiso d D 1 . . H
    H2 0.740(3) 0.451(2) 0.0259(13) 0.046(10) Uiso d D 1 . . H
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    C1 C2 . 1.498(5) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 C7 . 1.377(5) ?
    C2 C3 . 1.381(5) ?
    C3 C4 . 1.377(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.386(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.375(4) ?
    C5 S1 . 1.755(3) yes
    C6 C7 . 1.386(5) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C8 N1 . 1.482(4) yes
    C8 C9 . 1.509(4) ?
    C8 C13 . 1.518(4) ?
    C8 H8 . 0.9800 ?
    C9 C10 . 1.518(4) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C11 . 1.517(5) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C12 . 1.528(5) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C13 . 1.528(4) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 N2 . 1.448(4) yes
    C13 H13 . 0.9800 ?
    C14 O3 . 1.234(3) yes
    C14 N2 . 1.328(4) yes
    C14 C15 . 1.507(4) ?
    C15 N3 . 1.459(4) yes
    C15 C16 . 1.524(5) ?
    C15 H15 . 0.9800 ?
    C16 C17' . 1.479(9) ?
    C16 C17 . 1.496(5) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C16 H16C . 0.9867 ?
    C16 H16D . 0.9502 ?
    C17' C18 . 1.492(9) ?
    C17' H17D . 0.9700 ?
    C17' H17C . 0.9700 ?
    C17 C18 . 1.480(5) ?
    C17 H17B . 0.9700 ?
    C17 H17A . 0.9700 ?
    C18 N3 . 1.448(5) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C18 H18C . 0.9959 ?
    C18 H18D . 0.9365 ?
    N1 S1 . 1.611(3) yes
    N1 H1 . 0.846(10) ?
    N2 H2 . 0.860(10) ?
    N3 H3A . 0.860(10) ?
    O1 S1 . 1.430(2) yes
    O2 S1 . 1.429(2) yes
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
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C7 C2 C3 . . 116.9(4) ?
    C7 C2 C1 . . 121.6(4) ?
    C3 C2 C1 . . 121.5(4) ?
    C4 C3 C2 . . 122.3(4) ?
    C4 C3 H3 . . 118.9 ?
    C2 C3 H3 . . 118.9 ?
    C3 C4 C5 . . 119.4(3) ?
    C3 C4 H4 . . 120.3 ?
    C5 C4 H4 . . 120.3 ?
    C6 C5 C4 . . 119.6(3) ?
    C6 C5 S1 . . 119.2(3) ?
    C4 C5 S1 . . 121.1(3) ?
    C5 C6 C7 . . 119.5(3) ?
    C5 C6 H6 . . 120.3 ?
    C7 C6 H6 . . 120.3 ?
    C2 C7 C6 . . 122.2(4) ?
    C2 C7 H7 . . 118.9 ?
    C6 C7 H7 . . 118.9 ?
    N1 C8 C9 . . 110.1(3) ?
    N1 C8 C13 . . 110.9(2) ?
    C9 C8 C13 . . 111.4(3) ?
    N1 C8 H8 . . 108.1 ?
    C9 C8 H8 . . 108.1 ?
    C13 C8 H8 . . 108.1 ?
    C8 C9 C10 . . 113.0(3) ?
    C8 C9 H9A . . 109.0 ?
    C10 C9 H9A . . 109.0 ?
    C8 C9 H9B . . 109.0 ?
    C10 C9 H9B . . 109.0 ?
    H9A C9 H9B . . 107.8 ?
    C11 C10 C9 . . 110.1(3) ?
    C11 C10 H10A . . 109.6 ?
    C9 C10 H10A . . 109.6 ?
    C11 C10 H10B . . 109.6 ?
    C9 C10 H10B . . 109.6 ?
    H10A C10 H10B . . 108.2 ?
    C10 C11 C12 . . 109.7(3) ?
    C10 C11 H11A . . 109.7 ?
    C12 C11 H11A . . 109.7 ?
    C10 C11 H11B . . 109.7 ?
    C12 C11 H11B . . 109.7 ?
    H11A C11 H11B . . 108.2 ?
    C13 C12 C11 . . 110.9(3) ?
    C13 C12 H12A . . 109.5 ?
    C11 C12 H12A . . 109.5 ?
    C13 C12 H12B . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 108.1 ?
    N2 C13 C8 . . 110.8(3) ?
    N2 C13 C12 . . 111.5(3) ?
    C8 C13 C12 . . 110.5(2) ?
    N2 C13 H13 . . 108.0 ?
    C8 C13 H13 . . 108.0 ?
    C12 C13 H13 . . 108.0 ?
    O3 C14 N2 . . 122.9(3) ?
    O3 C14 C15 . . 121.0(3) ?
    N2 C14 C15 . . 116.1(3) ?
    N3 C15 C14 . . 112.8(3) ?
    N3 C15 C16 . . 106.4(3) ?
    C14 C15 C16 . . 111.7(3) ?
    N3 C15 H15 . . 108.6 ?
    C14 C15 H15 . . 108.6 ?
    C16 C15 H15 . . 108.6 ?
    C17' C16 C15 . . 99.5(8) ?
    C17 C16 C15 . . 106.5(4) ?
    C17 C16 H16A . . 110.4 ?
    C15 C16 H16A . . 110.4 ?
    C17 C16 H16B . . 110.4 ?
    C15 C16 H16B . . 110.4 ?
    H16A C16 H16B . . 108.6 ?
    C17' C16 H16C . . 111.1 ?
    C15 C16 H16C . . 111.2 ?
    C17' C16 H16D . . 112.0 ?
    C15 C16 H16D . . 113.0 ?
    H16C C16 H16D . . 109.8 ?
    C16 C17' C18 . . 103.9(8) ?
    C16 C17' H17D . . 111.0 ?
    C18 C17' H17D . . 111.0 ?
    C16 C17' H17C . . 111.0 ?
    C18 C17' H17C . . 111.0 ?
    H17D C17' H17C . . 109.0 ?
    C18 C17 C16 . . 103.7(4) ?
    C18 C17 H17B . . 111.0 ?
    C16 C17 H17B . . 111.0 ?
    C18 C17 H17A . . 111.0 ?
    C16 C17 H17A . . 111.0 ?
    H17B C17 H17A . . 109.0 ?
    C16 C17 H18D . . 127.5 ?
    H16D C17 H18D . . 125.5 ?
    N3 C18 C17 . . 108.5(4) ?
    N3 C18 C17' . . 103.1(8) ?
    N3 C18 H18A . . 110.0 ?
    C17 C18 H18A . . 110.0 ?
    N3 C18 H18B . . 110.0 ?
    C17 C18 H18B . . 110.0 ?
    H18A C18 H18B . . 108.4 ?
    N3 C18 H18C . . 109.8 ?
    C17' C18 H18C . . 109.5 ?
    N3 C18 H18D . . 113.0 ?
    C17' C18 H18D . . 111.6 ?
    H18C C18 H18D . . 109.6 ?
    C8 N1 S1 . . 119.1(2) ?
    C8 N1 H1 . . 115(2) ?
    S1 N1 H1 . . 112(2) ?
    C14 N2 C13 . . 124.4(3) ?
    C14 N2 H2 . . 112.9(19) ?
    C13 N2 H2 . . 122.7(19) ?
    C18 N3 C15 . . 107.9(3) ?
    C18 N3 H3A . . 110(2) ?
    C15 N3 H3A . . 108(2) ?
    O2 S1 O1 . . 119.23(16) ?
    O2 S1 N1 . . 107.05(15) ?
    O1 S1 N1 . . 106.94(15) ?
    O2 S1 C5 . . 107.66(16) ?
    O1 S1 C5 . . 108.28(15) ?
    N1 S1 C5 . . 107.12(14) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C7 C2 C3 C4 . . . . -3.9(5) ?
    C1 C2 C3 C4 . . . . 177.0(3) ?
    C2 C3 C4 C5 . . . . 2.2(5) ?
    C3 C4 C5 C6 . . . . 1.0(5) ?
    C3 C4 C5 S1 . . . . 176.6(3) ?
    C4 C5 C6 C7 . . . . -2.4(5) ?
    S1 C5 C6 C7 . . . . -178.1(3) ?
    C3 C2 C7 C6 . . . . 2.4(6) ?
    C1 C2 C7 C6 . . . . -178.4(4) ?
    C5 C6 C7 C2 . . . . 0.6(6) ?
    N1 C8 C9 C10 . . . . -177.1(3) ?
    C13 C8 C9 C10 . . . . -53.6(4) ?
    C8 C9 C10 C11 . . . . 55.5(4) ?
    C9 C10 C11 C12 . . . . -57.5(4) ?
    C10 C11 C12 C13 . . . . 59.3(4) ?
    N1 C8 C13 N2 . . . . -59.3(3) yes
    C9 C8 C13 N2 . . . . 177.7(3) ?
    N1 C8 C13 C12 . . . . 176.6(2) ?
    C9 C8 C13 C12 . . . . 53.6(3) ?
    C11 C12 C13 N2 . . . . 179.2(3) ?
    C11 C12 C13 C8 . . . . -57.1(4) ?
    O3 C14 C15 N3 . . . . 177.9(3) ?
    N2 C14 C15 N3 . . . . -2.3(4) ?
    O3 C14 C15 C16 . . . . -62.3(4) ?
    N2 C14 C15 C16 . . . . 117.4(3) ?
    N3 C15 C16 C17' . . . . 30.0(9) yes
    C14 C15 C16 C17' . . . . -93.4(9) ?
    N3 C15 C16 C17 . . . . -10.9(5) yes
    C14 C15 C16 C17 . . . . -134.3(4) ?
    C17 C16 C17' C18 . . . . 61.7(8) ?
    C15 C16 C17' C18 . . . . -42.7(15) ?
    C17' C16 C17 C18 . . . . -62.4(8) ?
    C15 C16 C17 C18 . . . . 22.8(6) ?
    C16 C17 C18 N3 . . . . -27.2(7) ?
    C16 C17 C18 C17' . . . . 61.4(8) ?
    C16 C17' C18 N3 . . . . 40.6(16) yes
    C16 C17' C18 C17 . . . . -62.7(8) ?
    C9 C8 N1 S1 . . . . -113.5(3) ?
    C13 C8 N1 S1 . . . . 122.7(2) ?
    O3 C14 N2 C13 . . . . 0.5(5) ?
    C15 C14 N2 C13 . . . . -179.2(3) yes
    C8 C13 N2 C14 . . . . 158.7(3) ?
    C12 C13 N2 C14 . . . . -77.8(4) ?
    C17 C18 N3 C15 . . . . 21.0(6) ?
    C17' C18 N3 C15 . . . . -20.7(9) ?
    C14 C15 N3 C18 . . . . 116.8(3) ?
    C16 C15 N3 C18 . . . . -5.9(4) yes
    C8 N1 S1 O2 . . . . -47.9(3) ?
    C8 N1 S1 O1 . . . . -176.7(2) ?
    C8 N1 S1 C5 . . . . 67.4(3) yes
    C6 C5 S1 O2 . . . . -162.5(3) ?
    C4 C5 S1 O2 . . . . 21.9(3) ?
    C6 C5 S1 O1 . . . . -32.4(3) ?
    C4 C5 S1 O1 . . . . 152.0(3) ?
    C6 C5 S1 N1 . . . . 82.7(3) ?
    C4 C5 S1 N1 . . . . -93.0(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
    N1 H1 O3 4_465 0.850(10)
                           2.140(10)
                                   2.961(4) 163(3)
    N2 H2 N3 . 0.860(10)
                       2.15(3) 2.660(4) 118(2)
    N2 H2 O2 . 0.860(10)
                       2.61(2) 3.288(4) 137(2)
    N3 H3A O1 4 0.860(10)
                        2.61(2) 3.411(4) 155(3)
    C13 H13 O1 4_565 0.98 2.55 3.506(4) 164
    C15 H15 O2 4 0.98 2.52 3.344(4) 142
