##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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     CrystalStructure_ver_3.5.1
_journal_date_recd_electronic     2007-03-19
_journal_date_accepted     2007-04-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      5
_journal_page_first     o2470
_journal_page_last     o2471
_journal_paper_category     EO
_journal_coeditor_code     TK2148
_publ_contact_author_name     'Jasinski, Jerry P.'
_publ_contact_author_address
;
Department of Chemistry
Keene State College
229 Main Street
Keene
NH 03435-2001
USA
;
_publ_contact_author_email     jjasinski@keene.edu
_publ_contact_author_fax     '603 358 2897'
_publ_contact_author_phone     '603 358 2563'
_publ_section_title
;\
4-Methoxy-4a-nitro-9-(phenylsulfonyl)-4,4a,9,9a-tetrahydro-1H-carbazol-\
2(3H)-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Kishbaugh, T. L. S.'
;
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
Keene
NH 03435-2001
USA
;
data_I
_chemical_name_systematic
;
4-Methoxy-4a-nitro-9-(phenylsulfonyl)-4,4a,9,9a-tetrahydro-1H-carbazol-2(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H18 N2 O6 S'
_chemical_formula_sum     'C19 H18 N2 O6 S'
_chemical_formula_iupac     'C19 H18 N2 O6 S'
_chemical_formula_weight     402.41
_chemical_melting_point     ?
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, z'
    'x, -y+1/2, z+1/2'
    '-x+1/2, -y, z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, -z'
    '-x, y-1/2, -z-1/2'
    'x-1/2, y, -z-1/2'
_cell_length_a     23.352(6)
_cell_length_b     15.085(14)
_cell_length_c     10.952(9)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     3858(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     17
_cell_measurement_theta_min     6.2
_cell_measurement_theta_max     11.8
_cell_measurement_temperature     296
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.386
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1680
_exptl_absorpt_coefficient_mu     0.207
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.922
_exptl_absorpt_correction_T_max     0.960
_exptl_special_details
;
IR (film): νₘₐₓ 1722 (C=O), 1361 (SO₂), 1166 (SO₂) cm⁻¹;
UV (EtOH): λₘₐₓ 256 nm;
¹H (CD₂Cl₂, δ, p.p.m.): 7.73--7.80 (m, 3H), 7.55--7.62 (m, 2H),
7.42--7.52 (m, 3H), 7.15--7.20 (m, 1H), 5.70 (dd, 1H, J= 2.2 and 6.2 Hz),
4.67 (m, 1H), 3.46 (s, 3H), 3.20 (dd, 1H, J= 6.2 and 16.5 Hz), 3.15 (dd, 1H,
J= 2.2 and 16.5 Hz), 2.67 (dd, 1H, J = 3 and 19 Hz), 1.92 (dd, 1H, J = 3 and
19 Hz);
¹³C (CD₂Cl₂, δ, p.p.m.): 204.2, 142.7, 136.2, 134.4, 133.5, 129.6,
127.9, 125.9, 125.6, 125.4, 116.8, 96.1, 20.5, 62.0, 58.3, 44.5, 37.7.
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku AFC-6S'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3333
_diffrn_reflns_av_R_equivalents     0.000
_diffrn_reflns_av_sigmaI/netI     0.326
_diffrn_reflns_theta_min     1.7
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     26.3
_diffrn_measured_fraction_theta_max     0.751
_diffrn_measured_fraction_theta_full     0.797
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     30
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     0
_diffrn_standards_number     3
_diffrn_standards_interval_count     150
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 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     3333
_reflns_number_gt     780
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.340
_refine_ls_R_factor_gt     0.055
_refine_ls_wR_factor_gt     0.129
_refine_ls_wR_factor_ref     0.255
_refine_ls_goodness_of_fit_ref     0.93
_refine_ls_restrained_S_all     0.93
_refine_ls_number_reflns     3333
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0932P)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     0.33
_refine_diff_density_min     -0.26
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.0038(7)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'H' 'H' 0.0000 0.0000
                         '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'
    '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'
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993)
;
_computing_cell_refinement     'MSC/AFC Diffractometer Control Software'
_computing_data_reduction     'CrystalStructure (Rigaku/MSC, 2005)'
_computing_structure_solution     'SIR92 (Altomare et al.,  1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'CrystalStructure'
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 0.84061(10) 0.18198(15) 0.7413(3) 0.0505(7) Uani d . 1 . .
    O O1 0.7979(2) 0.1863(4) 0.8320(6) 0.0639(19) Uani d . 1 . .
    O O2 0.8441(2) 0.2496(4) 0.6501(5) 0.0641(18) Uani d . 1 . .
    O O3 0.6950(3) -0.0144(5) 0.5633(8) 0.105(3) Uani d . 1 . .
    O O4 0.8504(3) -0.2176(4) 0.6132(7) 0.078(2) Uani d . 1 . .
    O O5 0.9466(3) -0.0745(6) 0.7608(9) 0.129(4) Uani d . 1 . .
    O O6 0.8836(4) -0.1376(7) 0.8624(9) 0.123(4) Uani d . 1 . .
    N N1 0.8284(3) 0.0872(5) 0.6691(7) 0.048(2) Uani d . 1 . .
    N N2 0.9004(5) -0.0946(6) 0.7770(9) 0.076(3) Uani d . 1 . .
    C C1 0.7518(4) -0.0115(6) 0.7442(9) 0.055(2) Uani d . 1 . .
    H H1 0.7420 -0.0540 0.8073 0.066 Uiso calc R 1 . .
    H H2 0.7311 0.0430 0.7608 0.066 Uiso calc R 1 . .
    C C2 0.7336(4) -0.0473(7) 0.6216(10) 0.058(3) Uani d . 1 . .
    C C3 0.7670(4) -0.1256(6) 0.5786(9) 0.065(3) Uani d . 1 . .
    H H3 0.7826 -0.1125 0.4985 0.077 Uiso calc R 1 . .
    H H4 0.7412 -0.1756 0.5700 0.077 Uiso calc R 1 . .
    C C4 0.8157(4) -0.1517(6) 0.6628(10) 0.058(3) Uani d . 1 . .
    H H5 0.7999 -0.1726 0.7406 0.070 Uiso calc R 1 . .
    C C5 0.8526(4) -0.0681(6) 0.6859(8) 0.050(2) Uani d . 1 . .
    C C6 0.8793(4) -0.0282(6) 0.5757(10) 0.054(3) Uani d . 1 . .
    C C7 0.9114(5) -0.0654(8) 0.4831(11) 0.089(4) Uani d . 1 . .
    H H6 0.9209 -0.1252 0.4853 0.107 Uiso calc R 1 . .
    C C8 0.9291(6) -0.0137(9) 0.3883(12) 0.112(5) Uani d . 1 . .
    H H7 0.9525 -0.0385 0.3288 0.135 Uiso calc R 1 . .
    C C9 0.9134(6) 0.0745(9) 0.3776(11) 0.105(5) Uani d . 1 . .
    H H8 0.9249 0.1074 0.3101 0.126 Uiso calc R 1 . .
    C C10 0.8808(5) 0.1126(7) 0.4671(10) 0.079(4) Uani d . 1 . .
    H H9 0.8703 0.1719 0.4610 0.095 Uiso calc R 1 . .
    C C11 0.8634(4) 0.0624(7) 0.5677(9) 0.055(3) Uani d . 1 . .
    C C12 0.8161(3) 0.0068(6) 0.7482(9) 0.051(2) Uani d . 1 . .
    H H18 0.8289 0.0169 0.8323 0.061 Uiso calc R 1 . .
    C C13 0.9083(4) 0.1725(6) 0.8130(9) 0.046(2) Uani d . 1 . .
    C C14 0.9130(4) 0.1361(6) 0.9278(10) 0.064(3) Uani d . 1 . .
    H H10 0.8805 0.1176 0.9695 0.077 Uiso calc R 1 . .
    C C15 0.9655(5) 0.1274(8) 0.9799(10) 0.081(4) Uani d . 1 . .
    H H11 0.9692 0.1015 1.0566 0.097 Uiso calc R 1 . .
    C C16 1.0124(5) 0.1566(9) 0.9195(13) 0.098(4) Uani d . 1 . .
    H H12 1.0481 0.1512 0.9561 0.117 Uiso calc R 1 . .
    C C17 1.0085(4) 0.1943(8) 0.8049(12) 0.085(4) Uani d . 1 . .
    H H13 1.0413 0.2152 0.7660 0.102 Uiso calc R 1 . .
    C C18 0.9562(4) 0.2009(6) 0.7487(10) 0.064(3) Uani d . 1 . .
    H H14 0.9529 0.2237 0.6701 0.077 Uiso calc R 1 . .
    C C19 0.8266(5) -0.3045(6) 0.6299(13) 0.115(5) Uani d . 1 . .
    H H15 0.8406 -0.3292 0.7050 0.138 Uiso calc R 1 . .
    H H16 0.8378 -0.3418 0.5631 0.138 Uiso calc R 1 . .
    H H17 0.7856 -0.3005 0.6328 0.138 Uiso calc R 1 . .
_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
    S1 O1 . 1.409(6) ?
    S1 O2 . 1.431(6) ?
    S1 N1 . 1.659(7) ?
    S1 C13 . 1.772(9) ?
    O3 C2 . 1.210(10) ?
    O4 C4 . 1.393(10) ?
    O4 C19 . 1.435(10) ?
    O5 N2 . 1.134(10) ?
    O6 N2 . 1.205(10) ?
    N1 C11 . 1.428(11) ?
    N1 C12 . 1.518(10) ?
    N2 C5 . 1.550(13) ?
    C1 C2 . 1.509(12) ?
    C1 C12 . 1.529(11) ?
    C1 H1 . 0.9700 ?
    C1 H2 . 0.9700 ?
    C2 C3 . 1.492(12) ?
    C3 C4 . 1.517(12) ?
    C3 H3 . 0.9700 ?
    C3 H4 . 0.9700 ?
    C4 C5 . 1.548(11) ?
    C4 H5 . 0.9800 ?
    C5 C6 . 1.486(12) ?
    C5 C12 . 1.571(11) ?
    C6 C7 . 1.380(12) ?
    C6 C11 . 1.419(12) ?
    C7 C8 . 1.362(14) ?
    C7 H6 . 0.9300 ?
    C8 C9 . 1.384(15) ?
    C8 H7 . 0.9300 ?
    C9 C10 . 1.368(13) ?
    C9 H8 . 0.9300 ?
    C10 C11 . 1.398(12) ?
    C10 H9 . 0.9300 ?
    C12 H18 . 0.9800 ?
    C13 C14 . 1.376(12) ?
    C13 C18 . 1.389(11) ?
    C14 C15 . 1.358(12) ?
    C14 H10 . 0.9300 ?
    C15 C16 . 1.353(14) ?
    C15 H11 . 0.9300 ?
    C16 C17 . 1.381(14) ?
    C16 H12 . 0.9300 ?
    C17 C18 . 1.372(12) ?
    C17 H13 . 0.9300 ?
    C18 H14 . 0.9300 ?
    C19 H15 . 0.9600 ?
    C19 H16 . 0.9600 ?
    C19 H17 . 0.9600 ?
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 . . 120.0(4) ?
    O1 S1 N1 . . 104.8(4) ?
    O2 S1 N1 . . 107.0(4) ?
    O1 S1 C13 . . 108.8(4) ?
    O2 S1 C13 . . 108.5(4) ?
    N1 S1 C13 . . 107.2(4) ?
    C4 O4 C19 . . 112.1(7) ?
    C11 N1 C12 . . 110.0(7) ?
    C11 N1 S1 . . 119.9(6) ?
    C12 N1 S1 . . 116.7(6) ?
    O5 N2 O6 . . 125.1(12) ?
    O5 N2 C5 . . 121.1(10) ?
    O6 N2 C5 . . 113.8(10) ?
    C2 C1 C12 . . 111.5(8) ?
    C2 C1 H1 . . 109.3 ?
    C12 C1 H1 . . 109.3 ?
    C2 C1 H2 . . 109.3 ?
    C12 C1 H2 . . 109.3 ?
    H1 C1 H2 . . 108.0 ?
    O3 C2 C3 . . 123.3(10) ?
    O3 C2 C1 . . 122.1(10) ?
    C3 C2 C1 . . 114.7(9) ?
    C2 C3 C4 . . 114.0(9) ?
    C2 C3 H3 . . 108.8 ?
    C4 C3 H3 . . 108.8 ?
    C2 C3 H4 . . 108.8 ?
    C4 C3 H4 . . 108.8 ?
    H3 C3 H4 . . 107.7 ?
    O4 C4 C3 . . 112.6(9) ?
    O4 C4 C5 . . 108.7(7) ?
    C3 C4 C5 . . 107.7(8) ?
    O4 C4 H5 . . 109.2 ?
    C3 C4 H5 . . 109.2 ?
    C5 C4 H5 . . 109.2 ?
    C6 C5 C4 . . 115.5(8) ?
    C6 C5 N2 . . 108.9(8) ?
    C4 C5 N2 . . 107.2(8) ?
    C6 C5 C12 . . 106.8(8) ?
    C4 C5 C12 . . 110.8(8) ?
    N2 C5 C12 . . 107.2(7) ?
    C7 C6 C11 . . 119.2(10) ?
    C7 C6 C5 . . 131.3(9) ?
    C11 C6 C5 . . 109.3(9) ?
    C8 C7 C6 . . 119.4(11) ?
    C8 C7 H6 . . 120.3 ?
    C6 C7 H6 . . 120.3 ?
    C7 C8 C9 . . 122.3(11) ?
    C7 C8 H7 . . 118.8 ?
    C9 C8 H7 . . 118.8 ?
    C10 C9 C8 . . 119.3(11) ?
    C10 C9 H8 . . 120.3 ?
    C8 C9 H8 . . 120.3 ?
    C9 C10 C11 . . 119.9(10) ?
    C9 C10 H9 . . 120.0 ?
    C11 C10 H9 . . 120.0 ?
    C10 C11 C6 . . 119.6(10) ?
    C10 C11 N1 . . 129.5(10) ?
    C6 C11 N1 . . 110.8(9) ?
    N1 C12 C1 . . 108.3(7) ?
    N1 C12 C5 . . 103.0(7) ?
    C1 C12 C5 . . 113.0(7) ?
    N1 C12 H18 . . 110.8 ?
    C1 C12 H18 . . 110.8 ?
    C5 C12 H18 . . 110.8 ?
    C14 C13 C18 . . 121.5(9) ?
    C14 C13 S1 . . 120.6(8) ?
    C18 C13 S1 . . 117.9(8) ?
    C15 C14 C13 . . 119.7(10) ?
    C15 C14 H10 . . 120.2 ?
    C13 C14 H10 . . 120.2 ?
    C16 C15 C14 . . 119.5(11) ?
    C16 C15 H11 . . 120.2 ?
    C14 C15 H11 . . 120.2 ?
    C15 C16 C17 . . 121.8(11) ?
    C15 C16 H12 . . 119.1 ?
    C17 C16 H12 . . 119.1 ?
    C18 C17 C16 . . 119.7(11) ?
    C18 C17 H13 . . 120.2 ?
    C16 C17 H13 . . 120.2 ?
    C17 C18 C13 . . 117.8(10) ?
    C17 C18 H14 . . 121.1 ?
    C13 C18 H14 . . 121.1 ?
    O4 C19 H15 . . 109.5 ?
    O4 C19 H16 . . 109.5 ?
    H15 C19 H16 . . 109.5 ?
    O4 C19 H17 . . 109.5 ?
    H15 C19 H17 . . 109.5 ?
    H16 C19 H17 . . 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 C11 . . . . 178.3(6) ?
    O2 S1 N1 C11 . . . . 50.0(7) ?
    C13 S1 N1 C11 . . . . -66.2(8) ?
    O1 S1 N1 C12 . . . . -44.7(7) ?
    O2 S1 N1 C12 . . . . -173.1(6) ?
    C13 S1 N1 C12 . . . . 70.8(7) ?
    C12 C1 C2 O3 . . . . -127.3(10) ?
    C12 C1 C2 C3 . . . . 52.4(10) ?
    O3 C2 C3 C4 . . . . 176.3(9) ?
    C1 C2 C3 C4 . . . . -3.4(11) ?
    C19 O4 C4 C3 . . . . -82.0(11) ?
    C19 O4 C4 C5 . . . . 158.8(9) ?
    C2 C3 C4 O4 . . . . -172.5(7) ?
    C2 C3 C4 C5 . . . . -52.6(11) ?
    O4 C4 C5 C6 . . . . 61.3(11) ?
    C3 C4 C5 C6 . . . . -61.0(11) ?
    O4 C4 C5 N2 . . . . -60.4(10) ?
    C3 C4 C5 N2 . . . . 177.3(8) ?
    O4 C4 C5 C12 . . . . -177.1(8) ?
    C3 C4 C5 C12 . . . . 60.6(10) ?
    O5 N2 C5 C6 . . . . 8.3(13) ?
    O6 N2 C5 C6 . . . . -171.1(9) ?
    O5 N2 C5 C4 . . . . 134.0(11) ?
    O6 N2 C5 C4 . . . . -45.5(12) ?
    O5 N2 C5 C12 . . . . -106.9(12) ?
    O6 N2 C5 C12 . . . . 73.6(11) ?
    C4 C5 C6 C7 . . . . -50.2(15) ?
    N2 C5 C6 C7 . . . . 70.5(12) ?
    C12 C5 C6 C7 . . . . -174.0(10) ?
    C4 C5 C6 C11 . . . . 124.9(9) ?
    N2 C5 C6 C11 . . . . -114.4(8) ?
    C12 C5 C6 C11 . . . . 1.1(10) ?
    C11 C6 C7 C8 . . . . 2.5(16) ?
    C5 C6 C7 C8 . . . . 177.3(11) ?
    C6 C7 C8 C9 . . . . -4(2) ?
    C7 C8 C9 C10 . . . . 3(2) ?
    C8 C9 C10 C11 . . . . -0.4(19) ?
    C9 C10 C11 C6 . . . . -0.5(15) ?
    C9 C10 C11 N1 . . . . -178.1(10) ?
    C7 C6 C11 C10 . . . . -0.5(14) ?
    C5 C6 C11 C10 . . . . -176.3(9) ?
    C7 C6 C11 N1 . . . . 177.5(8) ?
    C5 C6 C11 N1 . . . . 1.7(10) ?
    C12 N1 C11 C10 . . . . 173.8(9) ?
    S1 N1 C11 C10 . . . . -46.6(12) ?
    C12 N1 C11 C6 . . . . -3.9(9) ?
    S1 N1 C11 C6 . . . . 135.6(7) ?
    C11 N1 C12 C1 . . . . -115.6(8) ?
    S1 N1 C12 C1 . . . . 103.4(7) ?
    C11 N1 C12 C5 . . . . 4.3(8) ?
    S1 N1 C12 C5 . . . . -136.7(6) ?
    C2 C1 C12 N1 . . . . 71.3(9) ?
    C2 C1 C12 C5 . . . . -42.1(10) ?
    C6 C5 C12 N1 . . . . -3.2(9) ?
    C4 C5 C12 N1 . . . . -129.8(8) ?
    N2 C5 C12 N1 . . . . 113.4(8) ?
    C6 C5 C12 C1 . . . . 113.4(8) ?
    C4 C5 C12 C1 . . . . -13.3(11) ?
    N2 C5 C12 C1 . . . . -130.0(8) ?
    O1 S1 C13 C14 . . . . 25.9(8) ?
    O2 S1 C13 C14 . . . . 157.9(7) ?
    N1 S1 C13 C14 . . . . -86.9(8) ?
    O1 S1 C13 C18 . . . . -155.6(7) ?
    O2 S1 C13 C18 . . . . -23.5(8) ?
    N1 S1 C13 C18 . . . . 91.6(8) ?
    C18 C13 C14 C15 . . . . -0.1(15) ?
    S1 C13 C14 C15 . . . . 178.3(8) ?
    C13 C14 C15 C16 . . . . 1.6(16) ?
    C14 C15 C16 C17 . . . . -0.8(19) ?
    C15 C16 C17 C18 . . . . -1.5(19) ?
    C16 C17 C18 C13 . . . . 2.9(16) ?
    C14 C13 C18 C17 . . . . -2.1(14) ?
    S1 C13 C18 C17 . . . . 179.4(8) ?
