##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'manual editing of form.cif'
_journal_date_recd_electronic     2005-11-16
_journal_date_accepted     2005-11-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      1
_journal_page_first     o366
_journal_page_last     o367
_journal_paper_category     EO
_journal_coeditor_code     LH6553
_publ_contact_author
; Matthias Zeller
  Research Fellow and Adjunct Professor
  Department of Chemistry
  Youngstown State University
  1 University Plaza
  Youngstown, OH 44555-3663
  USA
;
_publ_contact_author_email     mzeller@cc.ysu.edu
_publ_contact_author_fax     '(330)941-1579'
_publ_contact_author_phone     '(330)941-7105'
_publ_section_title
;\
(4aSR,7RS,9aRS)-7-tert-Butyl-9a-methyl-5,5-dioxo-1,\
2,4a,9a-tetrahydro-8-oxa- 5λ⁶-thiabenzocycloheptan-9-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Zeller, Matthias'
; Department of Chemistry
  Youngstown State University
  1 University Plaza
  Youngstown, OH 44555-3663
  USA
;
    'Hunter, Allen D.'
; Department of Chemistry
  Youngstown State University
  1 University Plaza
  Youngstown, OH 44555-3663
  USA
;
    'Sampson, Paul'
; Department of Chemistry
  Kent State University
  PO Box 5190
  Kent, OH 44242-0001
  USA
;
    'Chumachenko, Nataliya'
; Department of Chemistry
  Kent State University
  PO Box 5190
  Kent, OH 44242-0001
  USA
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(4aSR,7RS,9aRS)-7-tert-Butyl-9a-methyl-5,5-dioxo-1,2,4a,9a-tetrahydro-8-oxa-
5λ⁶-thiabenzocycloheptan-9-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H22 O4 S'
_chemical_formula_sum     'C14 H22 O4 S'
_chemical_formula_iupac     'C14 H22 O4 S'
_chemical_formula_weight     286.38
_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     15.5204(7)
_cell_length_b     9.8367(4)
_cell_length_c     23.0445(10)
_cell_angle_alpha     90.00
_cell_angle_beta     124.6260(10)
_cell_angle_gamma     90.00
_cell_volume     2895.0(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     8187
_cell_measurement_theta_min     2.33
_cell_measurement_theta_max     30.52
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.43
_exptl_crystal_size_mid     0.42
_exptl_crystal_size_min     0.29
_exptl_crystal_density_diffrn     1.314
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1232
_exptl_absorpt_coefficient_mu     0.231
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS in SAINT-Plus; Bruker, 2003)'
_exptl_absorpt_correction_T_min     0.891
_exptl_absorpt_correction_T_max     0.935
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(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 AXS SMART APEX CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     29131
_diffrn_reflns_av_R_equivalents     0.0251
_diffrn_reflns_av_sigmaI/netI     0.0218
_diffrn_reflns_theta_min     1.59
_diffrn_reflns_theta_max     28.27
_diffrn_reflns_theta_full     28.27
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -20
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     30
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_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     7195
_reflns_number_gt     6801
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0404
_refine_ls_R_factor_gt     0.0383
_refine_ls_wR_factor_gt     0.0983
_refine_ls_wR_factor_ref     0.1000
_refine_ls_goodness_of_fit_ref     1.082
_refine_ls_restrained_S_all     1.082
_refine_ls_number_reflns     7195
_refine_ls_number_parameters     351
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0529P)²+1.2868P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.490
_refine_diff_density_min     -0.521
_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'
    '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, 2002)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2003)'
_computing_data_reduction     'SAINT-Plus'
_computing_structure_solution     'SHELXTL (Bruker, 2000)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_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
    C4A 0.56271(9) 0.31776(12) 0.15960(6) 0.0150(2) Uani d . 1 . . C
    H4A 0.6039 0.4000 0.1868 0.018 Uiso calc R 1 . . H
    C4 0.48733(10) 0.36073(13) 0.08363(6) 0.0195(2) Uani d . 1 . . C
    H4 0.4244 0.4052 0.0706 0.023 Uiso calc R 1 . . H
    C3 0.50479(10) 0.33945(15) 0.03439(7) 0.0241(3) Uani d . 1 . . C
    H3 0.4530 0.3666 -0.0126 0.029 Uiso calc R 1 . . H
    C2 0.60266(11) 0.27443(16) 0.04986(7) 0.0276(3) Uani d . 1 . . C
    H2A 0.6305 0.3288 0.0278 0.033 Uiso calc R 1 . . H
    H2B 0.5859 0.1826 0.0285 0.033 Uiso calc R 1 . . H
    C1 0.68671(10) 0.26253(15) 0.12893(7) 0.0226(3) Uani d . 1 . . C
    H1A 0.7187 0.3529 0.1477 0.027 Uiso calc R 1 . . H
    H1B 0.7424 0.2002 0.1366 0.027 Uiso calc R 1 . . H
    C9A 0.64168(9) 0.20860(12) 0.17001(6) 0.0158(2) Uani d . 1 . . C
    C9 0.73797(9) 0.19288(12) 0.24652(6) 0.0175(2) Uani d . 1 . . C
    C14 0.59384(10) 0.06641(13) 0.14206(7) 0.0213(2) Uani d . 1 . . C
    H14A 0.6439 0.0092 0.1401 0.032 Uiso calc R 1 . . H
    H14B 0.5292 0.0749 0.0947 0.032 Uiso calc R 1 . . H
    H14C 0.5780 0.0248 0.1736 0.032 Uiso calc R 1 . . H
    C6 0.57710(9) 0.20183(12) 0.27544(6) 0.0163(2) Uani d . 1 . . C
    H6A 0.5444 0.1921 0.3016 0.020 Uiso calc R 1 . . H
    H6B 0.5982 0.1102 0.2701 0.020 Uiso calc R 1 . . H
    C7 0.67399(9) 0.29122(12) 0.31767(6) 0.0159(2) Uani d . 1 . . C
    H10 0.6521 0.3884 0.3055 0.019 Uiso calc R 1 . . H
    C10 0.73170(10) 0.27344(12) 0.39810(6) 0.0187(2) Uani d . 1 . . C
    C12 0.82760(11) 0.36743(13) 0.43577(7) 0.0233(3) Uani d . 1 . . C
    H12A 0.8643 0.3573 0.4869 0.035 Uiso calc R 1 . . H
    H12B 0.8048 0.4619 0.4224 0.035 Uiso calc R 1 . . H
    H12C 0.8749 0.3430 0.4220 0.035 Uiso calc R 1 . . H
    C13 0.76640(12) 0.12601(14) 0.41940(8) 0.0313(3) Uani d . 1 . . C
    H13A 0.8026 0.1165 0.4705 0.047 Uiso calc R 1 . . H
    H13B 0.8139 0.1005 0.4060 0.047 Uiso calc R 1 . . H
    H13C 0.7049 0.0665 0.3953 0.047 Uiso calc R 1 . . H
    C11 0.65795(12) 0.31652(16) 0.41897(8) 0.0297(3) Uani d . 1 . . C
    H11A 0.6017 0.2494 0.4014 0.045 Uiso calc R 1 . . H
    H11B 0.6277 0.4056 0.3984 0.045 Uiso calc R 1 . . H
    H11C 0.6973 0.3221 0.4705 0.045 Uiso calc R 1 . . H
    O8 0.75025(7) 0.26132(11) 0.30171(5) 0.0241(2) Uani d . 1 . . O
    O3 0.81138(7) 0.12546(10) 0.25888(5) 0.0272(2) Uani d . 1 . . O
    O1 0.44413(7) 0.39477(9) 0.20021(5) 0.02007(19) Uani d . 1 . . O
    O2 0.41027(7) 0.16524(9) 0.14798(5) 0.01922(18) Uani d . 1 . . O
    S5 0.48443(2) 0.27000(3) 0.191055(15) 0.01392(8) Uani d . 1 . . S
    C4A' 0.91567(9) 0.81879(11) 0.30775(6) 0.0133(2) Uani d . 1 . . C
    H4A' 0.8856 0.9038 0.2792 0.016 Uiso calc R 1 . . H
    C4' 0.96606(9) 0.85685(12) 0.38410(6) 0.0178(2) Uani d . 1 . . C
    H4' 1.0342 0.8957 0.4095 0.021 Uiso calc R 1 . . H
    C3' 0.91974(10) 0.83864(13) 0.41727(6) 0.0195(2) Uani d . 1 . . C
    H3' 0.9565 0.8636 0.4656 0.023 Uiso calc R 1 . . H
    C2' 0.81195(10) 0.78037(13) 0.38187(7) 0.0192(2) Uani d . 1 . . C
    H2A' 0.7711 0.8365 0.3938 0.023 Uiso calc R 1 . . H
    H2B' 0.8169 0.6873 0.3999 0.023 Uiso calc R 1 . . H
    C1' 0.75484(9) 0.77511(13) 0.30203(6) 0.0177(2) Uani d . 1 . . C
    H1A' 0.7322 0.8680 0.2826 0.021 Uiso calc R 1 . . H
    H1B' 0.6914 0.7181 0.2818 0.021 Uiso calc R 1 . . H
    C9A' 0.82495(9) 0.71631(12) 0.27978(6) 0.0146(2) Uani d . 1 . . C
    C9' 0.75265(10) 0.70549(13) 0.19906(6) 0.0182(2) Uani d . 1 . . C
    C14' 0.85954(10) 0.57153(12) 0.30961(7) 0.0186(2) Uani d . 1 . . C
    H14D 0.7985 0.5192 0.2992 0.028 Uiso calc R 1 . . H
    H14E 0.9111 0.5762 0.3608 0.028 Uiso calc R 1 . . H
    H14F 0.8910 0.5270 0.2878 0.028 Uiso calc R 1 . . H
    C6' 0.94934(9) 0.70437(12) 0.21156(6) 0.0152(2) Uani d . 1 . . C
    H6A' 0.9989 0.6923 0.1979 0.018 Uiso calc R 1 . . H
    H6B' 0.9180 0.6147 0.2084 0.018 Uiso calc R 1 . . H
    C7' 0.86322(9) 0.80257(12) 0.16043(6) 0.0150(2) Uani d . 1 . . C
    H30 0.8883 0.8976 0.1766 0.018 Uiso calc R 1 . . H
    C10' 0.83126(10) 0.78739(13) 0.08382(6) 0.0176(2) Uani d . 1 . . C
    C11' 0.92497(11) 0.82562(17) 0.08147(7) 0.0286(3) Uani d . 1 . . C
    H11F 0.9803 0.7574 0.1072 0.043 Uiso calc R 1 . . H
    H11E 0.9516 0.9149 0.1034 0.043 Uiso calc R 1 . . H
    H11D 0.9029 0.8289 0.0323 0.043 Uiso calc R 1 . . H
    C12' 0.79615(10) 0.64169(13) 0.05758(7) 0.0230(3) Uani d . 1 . . C
    H12D 0.7379 0.6175 0.0609 0.035 Uiso calc R 1 . . H
    H12E 0.8547 0.5792 0.0866 0.035 Uiso calc R 1 . . H
    H12F 0.7734 0.6350 0.0084 0.035 Uiso calc R 1 . . H
    C13' 0.74216(11) 0.88755(13) 0.03734(7) 0.0235(3) Uani d . 1 . . C
    H13D 0.7227 0.8821 -0.0112 0.035 Uiso calc R 1 . . H
    H13E 0.7653 0.9801 0.0553 0.035 Uiso calc R 1 . . H
    H13F 0.6814 0.8645 0.0382 0.035 Uiso calc R 1 . . H
    O8' 0.76699(7) 0.78213(10) 0.15664(5) 0.0226(2) Uani d . 1 . . O
    O3' 0.67514(8) 0.63644(12) 0.17150(5) 0.0334(2) Uani d . 1 . . O
    O2' 1.07623(7) 0.65207(9) 0.34704(5) 0.01866(18) Uani d . 1 . . O
    O1' 1.07662(6) 0.88352(9) 0.30531(5) 0.01784(18) Uani d . 1 . . O
    S5' 1.01848(2) 0.76324(3) 0.299595(15) 0.01311(8) Uani d . 1 . . S
_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
    C4A C4 . 1.5116(16) ?
    C4A C9A . 1.5422(16) ?
    C4A S5 . 1.7953(12) ?
    C4A H4A . 1.0000 ?
    C4 C3 . 1.3245(18) ?
    C4 H4 . 0.9500 ?
    C3 C2 . 1.493(2) ?
    C3 H3 . 0.9500 ?
    C2 C1 . 1.5278(19) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C1 C9A . 1.5552(17) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C9A C9 . 1.5400(16) ?
    C9A C14 . 1.5424(17) ?
    C9 O3 . 1.2043(15) ?
    C9 O8 . 1.3534(15) ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    C6 C7 . 1.5226(16) ?
    C6 S5 . 1.7668(12) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 O8 . 1.4552(15) ?
    C7 C10 . 1.5433(16) ?
    C7 H10 . 1.0000 ?
    C10 C13 . 1.5276(18) ?
    C10 C11 . 1.5318(19) ?
    C10 C12 . 1.5347(17) ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    O1 S5 . 1.4464(9) ?
    O2 S5 . 1.4400(9) ?
    C4A' C4' . 1.5113(16) ?
    C4A' C9A' . 1.5437(15) ?
    C4A' S5' . 1.7945(11) ?
    C4A' H4A' . 1.0000 ?
    C4' C3' . 1.3256(17) ?
    C4' H4' . 0.9500 ?
    C3' C2' . 1.4973(18) ?
    C3' H3' . 0.9500 ?
    C2' C1' . 1.5232(17) ?
    C2' H2A' . 0.9900 ?
    C2' H2B' . 0.9900 ?
    C1' C9A' . 1.5541(16) ?
    C1' H1A' . 0.9900 ?
    C1' H1B' . 0.9900 ?
    C9A' C9' . 1.5357(16) ?
    C9A' C14' . 1.5394(16) ?
    C9' O3' . 1.2015(16) ?
    C9' O8' . 1.3495(15) ?
    C14' H14D . 0.9800 ?
    C14' H14E . 0.9800 ?
    C14' H14F . 0.9800 ?
    C6' C7' . 1.5226(16) ?
    C6' S5' . 1.7689(12) ?
    C6' H6A' . 0.9900 ?
    C6' H6B' . 0.9900 ?
    C7' O8' . 1.4596(14) ?
    C7' C10' . 1.5459(16) ?
    C7' H30 . 1.0000 ?
    C10' C12' . 1.5304(17) ?
    C10' C13' . 1.5320(18) ?
    C10' C11' . 1.5327(18) ?
    C11' H11F . 0.9800 ?
    C11' H11E . 0.9800 ?
    C11' H11D . 0.9800 ?
    C12' H12D . 0.9800 ?
    C12' H12E . 0.9800 ?
    C12' H12F . 0.9800 ?
    C13' H13D . 0.9800 ?
    C13' H13E . 0.9800 ?
    C13' H13F . 0.9800 ?
    O2' S5' . 1.4426(9) ?
    O1' S5' . 1.4479(9) ?
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
    C4 C4A C9A . . 113.48(10) ?
    C4 C4A S5 . . 106.55(8) ?
    C9A C4A S5 . . 114.54(8) ?
    C4 C4A H4A . . 107.3 ?
    C9A C4A H4A . . 107.3 ?
    S5 C4A H4A . . 107.3 ?
    C3 C4 C4A . . 123.20(12) ?
    C3 C4 H4 . . 118.4 ?
    C4A C4 H4 . . 118.4 ?
    C4 C3 C2 . . 122.61(12) ?
    C4 C3 H3 . . 118.7 ?
    C2 C3 H3 . . 118.7 ?
    C3 C2 C1 . . 112.41(11) ?
    C3 C2 H2A . . 109.1 ?
    C1 C2 H2A . . 109.1 ?
    C3 C2 H2B . . 109.1 ?
    C1 C2 H2B . . 109.1 ?
    H2A C2 H2B . . 107.9 ?
    C2 C1 C9A . . 112.18(10) ?
    C2 C1 H1A . . 109.2 ?
    C9A C1 H1A . . 109.2 ?
    C2 C1 H1B . . 109.2 ?
    C9A C1 H1B . . 109.2 ?
    H1A C1 H1B . . 107.9 ?
    C9 C9A C4A . . 114.61(10) ?
    C9 C9A C14 . . 108.10(10) ?
    C4A C9A C14 . . 114.52(10) ?
    C9 C9A C1 . . 104.58(10) ?
    C4A C9A C1 . . 105.08(10) ?
    C14 C9A C1 . . 109.35(10) ?
    O3 C9 O8 . . 116.26(11) ?
    O3 C9 C9A . . 119.89(11) ?
    O8 C9 C9A . . 123.56(10) ?
    C9A C14 H14A . . 109.5 ?
    C9A C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C9A C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C7 C6 S5 . . 112.02(8) ?
    C7 C6 H6A . . 109.2 ?
    S5 C6 H6A . . 109.2 ?
    C7 C6 H6B . . 109.2 ?
    S5 C6 H6B . . 109.2 ?
    H6A C6 H6B . . 107.9 ?
    O8 C7 C6 . . 111.81(10) ?
    O8 C7 C10 . . 106.28(10) ?
    C6 C7 C10 . . 112.99(10) ?
    O8 C7 H10 . . 108.5 ?
    C6 C7 H10 . . 108.5 ?
    C10 C7 H10 . . 108.5 ?
    C13 C10 C11 . . 110.59(12) ?
    C13 C10 C12 . . 109.80(11) ?
    C11 C10 C12 . . 108.26(11) ?
    C13 C10 C7 . . 110.58(10) ?
    C11 C10 C7 . . 108.57(11) ?
    C12 C10 C7 . . 108.99(10) ?
    C10 C12 H12A . . 109.5 ?
    C10 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C10 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C10 C13 H13A . . 109.5 ?
    C10 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C10 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C9 O8 C7 . . 129.61(10) ?
    O2 S5 O1 . . 117.73(5) ?
    O2 S5 C6 . . 108.61(5) ?
    O1 S5 C6 . . 108.10(6) ?
    O2 S5 C4A . . 111.60(5) ?
    O1 S5 C4A . . 106.54(5) ?
    C6 S5 C4A . . 103.26(5) ?
    C4' C4A' C9A' . . 113.18(9) ?
    C4' C4A' S5' . . 107.14(8) ?
    C9A' C4A' S5' . . 114.32(8) ?
    C4' C4A' H4A' . . 107.3 ?
    C9A' C4A' H4A' . . 107.3 ?
    S5' C4A' H4A' . . 107.3 ?
    C3' C4' C4A' . . 123.12(11) ?
    C3' C4' H4' . . 118.4 ?
    C4A' C4' H4' . . 118.4 ?
    C4' C3' C2' . . 122.80(11) ?
    C4' C3' H3' . . 118.6 ?
    C2' C3' H3' . . 118.6 ?
    C3' C2' C1' . . 111.98(10) ?
    C3' C2' H2A' . . 109.2 ?
    C1' C2' H2A' . . 109.2 ?
    C3' C2' H2B' . . 109.2 ?
    C1' C2' H2B' . . 109.2 ?
    H2A' C2' H2B' . . 107.9 ?
    C2' C1' C9A' . . 112.04(10) ?
    C2' C1' H1A' . . 109.2 ?
    C9A' C1' H1A' . . 109.2 ?
    C2' C1' H1B' . . 109.2 ?
    C9A' C1' H1B' . . 109.2 ?
    H1A' C1' H1B' . . 107.9 ?
    C9' C9A' C14' . . 107.83(10) ?
    C9' C9A' C4A' . . 114.60(10) ?
    C14' C9A' C4A' . . 114.45(10) ?
    C9' C9A' C1' . . 104.99(9) ?
    C14' C9A' C1' . . 109.20(9) ?
    C4A' C9A' C1' . . 105.24(9) ?
    O3' C9' O8' . . 117.43(11) ?
    O3' C9' C9A' . . 120.16(11) ?
    O8' C9' C9A' . . 122.07(11) ?
    C9A' C14' H14D . . 109.5 ?
    C9A' C14' H14E . . 109.5 ?
    H14D C14' H14E . . 109.5 ?
    C9A' C14' H14F . . 109.5 ?
    H14D C14' H14F . . 109.5 ?
    H14E C14' H14F . . 109.5 ?
    C7' C6' S5' . . 111.93(8) ?
    C7' C6' H6A' . . 109.2 ?
    S5' C6' H6A' . . 109.2 ?
    C7' C6' H6B' . . 109.2 ?
    S5' C6' H6B' . . 109.2 ?
    H6A' C6' H6B' . . 107.9 ?
    O8' C7' C6' . . 112.17(9) ?
    O8' C7' C10' . . 105.36(9) ?
    C6' C7' C10' . . 113.16(10) ?
    O8' C7' H30 . . 108.7 ?
    C6' C7' H30 . . 108.7 ?
    C10' C7' H30 . . 108.7 ?
    C12' C10' C13' . . 110.41(10) ?
    C12' C10' C11' . . 110.35(11) ?
    C13' C10' C11' . . 108.37(11) ?
    C12' C10' C7' . . 110.67(10) ?
    C13' C10' C7' . . 108.23(10) ?
    C11' C10' C7' . . 108.75(10) ?
    C10' C11' H11F . . 109.5 ?
    C10' C11' H11E . . 109.5 ?
    H11F C11' H11E . . 109.5 ?
    C10' C11' H11D . . 109.5 ?
    H11F C11' H11D . . 109.5 ?
    H11E C11' H11D . . 109.5 ?
    C10' C12' H12D . . 109.5 ?
    C10' C12' H12E . . 109.5 ?
    H12D C12' H12E . . 109.5 ?
    C10' C12' H12F . . 109.5 ?
    H12D C12' H12F . . 109.5 ?
    H12E C12' H12F . . 109.5 ?
    C10' C13' H13D . . 109.5 ?
    C10' C13' H13E . . 109.5 ?
    H13D C13' H13E . . 109.5 ?
    C10' C13' H13F . . 109.5 ?
    H13D C13' H13F . . 109.5 ?
    H13E C13' H13F . . 109.5 ?
    C9' O8' C7' . . 128.17(10) ?
    O2' S5' O1' . . 117.63(5) ?
    O2' S5' C6' . . 109.38(5) ?
    O1' S5' C6' . . 108.20(5) ?
    O2' S5' C4A' . . 110.97(5) ?
    O1' S5' C4A' . . 106.67(5) ?
    C6' S5' C4A' . . 102.93(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
    C9A C4A C4 C3 . . . . -18.83(17) ?
    S5 C4A C4 C3 . . . . -145.81(12) ?
    C4A C4 C3 C2 . . . . -1.9(2) ?
    C4 C3 C2 C1 . . . . -11.5(2) ?
    C3 C2 C1 C9A . . . . 45.44(16) ?
    C4 C4A C9A C9 . . . . 162.93(10) ?
    S5 C4A C9A C9 . . . . -74.41(12) ?
    C4 C4A C9A C14 . . . . -71.29(13) ?
    S5 C4A C9A C14 . . . . 51.37(12) ?
    C4 C4A C9A C1 . . . . 48.71(13) ?
    S5 C4A C9A C1 . . . . 171.38(8) ?
    C2 C1 C9A C9 . . . . 175.64(11) ?
    C2 C1 C9A C4A . . . . -63.31(14) ?
    C2 C1 C9A C14 . . . . 60.07(14) ?
    C4A C9A C9 O3 . . . . -169.14(11) ?
    C14 C9A C9 O3 . . . . 61.82(15) ?
    C1 C9A C9 O3 . . . . -54.63(15) ?
    C4A C9A C9 O8 . . . . 4.51(16) ?
    C14 C9A C9 O8 . . . . -124.54(12) ?
    C1 C9A C9 O8 . . . . 119.02(12) ?
    S5 C6 C7 O8 . . . . -85.31(11) ?
    S5 C6 C7 C10 . . . . 154.84(9) ?
    O8 C7 C10 C13 . . . . -63.71(13) ?
    C6 C7 C10 C13 . . . . 59.27(14) ?
    O8 C7 C10 C11 . . . . 174.80(10) ?
    C6 C7 C10 C11 . . . . -62.22(13) ?
    O8 C7 C10 C12 . . . . 57.08(13) ?
    C6 C7 C10 C12 . . . . -179.94(10) ?
    O3 C9 O8 C7 . . . . -144.94(13) ?
    C9A C9 O8 C7 . . . . 41.20(19) ?
    C6 C7 O8 C9 . . . . 16.62(17) ?
    C10 C7 O8 C9 . . . . 140.34(12) ?
    C7 C6 S5 O2 . . . . 164.46(8) ?
    C7 C6 S5 O1 . . . . -66.75(10) ?
    C7 C6 S5 C4A . . . . 45.88(10) ?
    C4 C4A S5 O2 . . . . 56.44(9) ?
    C9A C4A S5 O2 . . . . -69.90(10) ?
    C4 C4A S5 O1 . . . . -73.32(9) ?
    C9A C4A S5 O1 . . . . 160.33(8) ?
    C4 C4A S5 C6 . . . . 172.92(8) ?
    C9A C4A S5 C6 . . . . 46.58(10) ?
    C9A' C4A' C4' C3' . . . . -19.11(16) ?
    S5' C4A' C4' C3' . . . . -146.04(11) ?
    C4A' C4' C3' C2' . . . . -0.98(19) ?
    C4' C3' C2' C1' . . . . -12.66(17) ?
    C3' C2' C1' C9A' . . . . 46.36(14) ?
    C4' C4A' C9A' C9' . . . . 163.66(10) ?
    S5' C4A' C9A' C9' . . . . -73.30(11) ?
    C4' C4A' C9A' C14' . . . . -71.03(12) ?
    S5' C4A' C9A' C14' . . . . 52.01(12) ?
    C4' C4A' C9A' C1' . . . . 48.85(12) ?
    S5' C4A' C9A' C1' . . . . 171.90(8) ?
    C2' C1' C9A' C9' . . . . 174.67(10) ?
    C2' C1' C9A' C14' . . . . 59.27(13) ?
    C2' C1' C9A' C4A' . . . . -64.03(12) ?
    C14' C9A' C9' O3' . . . . 56.81(16) ?
    C4A' C9A' C9' O3' . . . . -174.48(12) ?
    C1' C9A' C9' O3' . . . . -59.53(15) ?
    C14' C9A' C9' O8' . . . . -130.00(12) ?
    C4A' C9A' C9' O8' . . . . -1.30(16) ?
    C1' C9A' C9' O8' . . . . 113.65(12) ?
    S5' C6' C7' O8' . . . . -83.72(11) ?
    S5' C6' C7' C10' . . . . 157.24(8) ?
    O8' C7' C10' C12' . . . . -65.89(12) ?
    C6' C7' C10' C12' . . . . 57.02(13) ?
    O8' C7' C10' C13' . . . . 55.22(12) ?
    C6' C7' C10' C13' . . . . 178.12(10) ?
    O8' C7' C10' C11' . . . . 172.74(10) ?
    C6' C7' C10' C11' . . . . -64.35(13) ?
    O3' C9' O8' C7' . . . . -136.71(13) ?
    C9A' C9' O8' C7' . . . . 49.93(18) ?
    C6' C7' O8' C9' . . . . 11.00(17) ?
    C10' C7' O8' C9' . . . . 134.54(12) ?
    C7' C6' S5' O2' . . . . 163.20(8) ?
    C7' C6' S5' O1' . . . . -67.51(9) ?
    C7' C6' S5' C4A' . . . . 45.16(9) ?
    C4' C4A' S5' O2' . . . . 56.87(9) ?
    C9A' C4A' S5' O2' . . . . -69.39(9) ?
    C4' C4A' S5' O1' . . . . -72.43(9) ?
    C9A' C4A' S5' O1' . . . . 161.32(8) ?
    C4' C4A' S5' C6' . . . . 173.78(8) ?
    C9A' C4A' S5' C6' . . . . 47.53(9) ?
