# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Ya-Wen Zhang'
_publ_contact_author_email       ZHANGYW@SUDA.EDU.CN

_publ_section_title              
;
Dynamic kinetic resolution of beta-keto sulfones via
asymmetric transfer hydrogenation
;
loop_
_publ_author_name
'Ya-Wen Zhang.'
'Zhenhua Ding.'
'Zongxuan Shen.'
'Ting Wang.'
'Jin Yang.'

# Attachment 'shelxl.cif'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 696276'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H32 O6 S2'
_chemical_formula_sum            'C30 H32 O6 S2'
_chemical_formula_weight         552.68
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.4899(19)
_cell_length_b                   11.433(2)
_cell_length_c                   11.813(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.702(4)
_cell_angle_gamma                90.00
_cell_volume                     1392.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4985
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      25.3

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13600
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         25.35
_reflns_number_total             4605
_reflns_number_gt                3853
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.2275P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(8)
_refine_ls_number_reflns         4605
_refine_ls_number_parameters     348
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.56153(8) 0.16372(8) 0.10842(7) 0.0574(3) Uani 1 1 d . . .
S2 S 0.08339(9) 0.59433(8) 0.10946(7) 0.0628(3) Uani 1 1 d . . .
O1 O 0.8684(2) 0.1385(3) 0.2058(2) 0.0792(9) Uani 1 1 d . . .
H1 H 0.8615 0.1432 0.1357 0.119 Uiso 1 1 calc R . .
O2 O 0.6134(2) 0.0691(3) 0.0490(2) 0.0740(8) Uani 1 1 d . . .
O3 O 0.5538(3) 0.2783(3) 0.0575(2) 0.0838(9) Uani 1 1 d . . .
O4 O 0.3693(3) 0.5040(2) 0.1824(2) 0.0721(7) Uani 1 1 d . . .
H4 H 0.3785 0.5075 0.1151 0.108 Uiso 1 1 calc R . .
O5 O 0.0659(3) 0.4727(3) 0.0843(3) 0.1018(11) Uani 1 1 d . . .
O6 O 0.1278(2) 0.6701(3) 0.0265(2) 0.0858(9) Uani 1 1 d . . .
C1 C 0.7916(3) 0.2254(3) 0.2446(3) 0.0577(9) Uani 1 1 d . . .
H1A H 0.7817 0.2908 0.1901 0.069 Uiso 1 1 calc R . .
C2 C 0.6561(3) 0.1769(3) 0.2515(3) 0.0517(8) Uani 1 1 d . . .
H2 H 0.6129 0.2345 0.2930 0.062 Uiso 1 1 calc R . .
C3 C 0.6612(4) 0.0628(4) 0.3166(3) 0.0733(11) Uani 1 1 d . . .
H3A H 0.7038 0.0047 0.2782 0.110 Uiso 1 1 calc R . .
H3B H 0.5746 0.0375 0.3194 0.110 Uiso 1 1 calc R . .
H3C H 0.7085 0.0738 0.3936 0.110 Uiso 1 1 calc R . .
C4 C 0.4057(3) 0.1205(3) 0.1286(3) 0.0522(9) Uani 1 1 d . . .
C5 C 0.3231(3) 0.2015(4) 0.1631(3) 0.0648(10) Uani 1 1 d . . .
H5 H 0.3487 0.2791 0.1750 0.078 Uiso 1 1 calc R . .
C6 C 0.2028(3) 0.1665(4) 0.1797(3) 0.0725(11) Uani 1 1 d . . .
H6 H 0.1467 0.2206 0.2031 0.087 Uiso 1 1 calc R . .
C7 C 0.1652(4) 0.0532(4) 0.1623(3) 0.0707(11) Uani 1 1 d . . .
H7 H 0.0842 0.0299 0.1755 0.085 Uiso 1 1 calc R . .
C8 C 0.2456(4) -0.0272(4) 0.1254(4) 0.0732(12) Uani 1 1 d . . .
H8 H 0.2181 -0.1040 0.1117 0.088 Uiso 1 1 calc R . .
C9 C 0.3679(3) 0.0058(3) 0.1083(3) 0.0623(10) Uani 1 1 d . . .
H9 H 0.4231 -0.0482 0.0837 0.075 Uiso 1 1 calc R . .
C10 C 0.8602(3) 0.2691(3) 0.3617(3) 0.0547(8) Uani 1 1 d . . .
C11 C 0.9720(4) 0.2183(4) 0.4182(4) 0.0819(13) Uani 1 1 d . . .
H11 H 1.0070 0.1552 0.3848 0.098 Uiso 1 1 calc R . .
C12 C 1.0339(5) 0.2598(5) 0.5244(4) 0.0979(15) Uani 1 1 d . . .
H12 H 1.1088 0.2227 0.5621 0.117 Uiso 1 1 calc R . .
C13 C 0.9884(5) 0.3519(5) 0.5739(4) 0.0970(15) Uani 1 1 d . . .
H13 H 1.0315 0.3795 0.6448 0.116 Uiso 1 1 calc R . .
C14 C 0.8764(5) 0.4054(5) 0.5182(5) 0.1134(19) Uani 1 1 d . . .
H14 H 0.8432 0.4696 0.5515 0.136 Uiso 1 1 calc R . .
C15 C 0.8133(4) 0.3634(4) 0.4121(4) 0.0907(14) Uani 1 1 d . . .
H15 H 0.7379 0.4001 0.3748 0.109 Uiso 1 1 calc R . .
C16 C 0.3340(3) 0.6154(3) 0.2184(3) 0.0583(9) Uani 1 1 d . . .
H16 H 0.3372 0.6715 0.1563 0.070 Uiso 1 1 calc R . .
C17 C 0.1957(3) 0.6135(3) 0.2432(3) 0.0556(9) Uani 1 1 d . . .
H17 H 0.1788 0.6903 0.2742 0.067 Uiso 1 1 calc R . .
C18 C 0.1733(4) 0.5217(4) 0.3309(3) 0.0813(12) Uani 1 1 d . . .
H18A H 0.1890 0.4453 0.3027 0.122 Uiso 1 1 calc R . .
H18B H 0.0854 0.5265 0.3427 0.122 Uiso 1 1 calc R . .
H18C H 0.2315 0.5355 0.4025 0.122 Uiso 1 1 calc R . .
C19 C -0.0645(3) 0.6512(3) 0.1335(3) 0.0510(8) Uani 1 1 d . . .
C20 C -0.0915(4) 0.7675(4) 0.1091(3) 0.0643(10) Uani 1 1 d . . .
H20 H -0.0315 0.8143 0.0815 0.077 Uiso 1 1 calc R . .
C21 C -0.2084(4) 0.8142(4) 0.1258(4) 0.0819(13) Uani 1 1 d . . .
H21 H -0.2268 0.8927 0.1100 0.098 Uiso 1 1 calc R . .
C22 C -0.2951(4) 0.7460(6) 0.1648(4) 0.0900(16) Uani 1 1 d . . .
H22 H -0.3730 0.7779 0.1769 0.108 Uiso 1 1 calc R . .
C23 C -0.2700(4) 0.6311(6) 0.1867(4) 0.1005(18) Uani 1 1 d . . .
H23 H -0.3319 0.5846 0.2121 0.121 Uiso 1 1 calc R . .
C24 C -0.1534(4) 0.5819(4) 0.1719(3) 0.0807(12) Uani 1 1 d . . .
H24 H -0.1362 0.5032 0.1878 0.097 Uiso 1 1 calc R . .
C25 C 0.4285(3) 0.6547(3) 0.3245(3) 0.0552(8) Uani 1 1 d . . .
C26 C 0.5069(4) 0.5771(4) 0.3933(4) 0.0818(12) Uani 1 1 d . . .
H26 H 0.5030 0.4980 0.3743 0.098 Uiso 1 1 calc R . .
C27 C 0.5919(4) 0.6144(6) 0.4908(4) 0.1007(16) Uani 1 1 d . . .
H27 H 0.6436 0.5604 0.5372 0.121 Uiso 1 1 calc R . .
C28 C 0.5997(5) 0.7291(6) 0.5183(4) 0.0976(15) Uani 1 1 d . . .
H28 H 0.6557 0.7538 0.5844 0.117 Uiso 1 1 calc R . .
C29 C 0.5268(6) 0.8077(5) 0.4505(4) 0.1089(17) Uani 1 1 d . . .
H29 H 0.5347 0.8869 0.4681 0.131 Uiso 1 1 calc R . .
C30 C 0.4395(5) 0.7701(4) 0.3541(4) 0.0883(13) Uani 1 1 d . . .
H30 H 0.3875 0.8248 0.3089 0.106 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0528(5) 0.0745(7) 0.0442(5) 0.0063(5) 0.0072(3) -0.0098(5)
S2 0.0629(6) 0.0780(7) 0.0469(5) -0.0093(5) 0.0088(4) 0.0124(5)
O1 0.0564(15) 0.131(3) 0.0529(14) -0.0065(17) 0.0161(12) 0.0154(15)
O2 0.0662(16) 0.106(2) 0.0556(14) -0.0230(15) 0.0254(12) -0.0035(14)
O3 0.0809(18) 0.087(2) 0.0745(19) 0.0339(17) -0.0080(14) -0.0223(15)
O4 0.0859(18) 0.0739(18) 0.0603(16) -0.0091(14) 0.0234(14) 0.0149(14)
O5 0.106(2) 0.080(2) 0.108(2) -0.0426(19) -0.0114(18) 0.0191(17)
O6 0.0646(15) 0.152(3) 0.0447(13) 0.0136(18) 0.0197(11) 0.0169(18)
C1 0.0480(19) 0.077(2) 0.049(2) 0.0082(18) 0.0117(16) 0.0015(17)
C2 0.0511(18) 0.063(2) 0.0424(17) 0.0018(18) 0.0131(14) -0.0046(17)
C3 0.075(3) 0.089(3) 0.056(2) 0.017(2) 0.0131(18) -0.011(2)
C4 0.0467(18) 0.069(3) 0.0410(18) -0.0016(16) 0.0080(14) -0.0004(16)
C5 0.057(2) 0.071(3) 0.064(2) -0.012(2) 0.0062(18) 0.0010(18)
C6 0.049(2) 0.101(3) 0.068(2) -0.012(3) 0.0091(17) 0.017(2)
C7 0.043(2) 0.101(3) 0.066(2) 0.008(2) 0.0054(18) -0.004(2)
C8 0.057(2) 0.074(3) 0.082(3) 0.011(2) -0.003(2) -0.014(2)
C9 0.057(2) 0.061(2) 0.067(2) -0.003(2) 0.0060(17) -0.0002(18)
C10 0.050(2) 0.069(2) 0.0441(18) 0.0042(18) 0.0068(15) -0.0054(17)
C11 0.065(3) 0.115(3) 0.059(2) -0.004(2) -0.004(2) 0.015(2)
C12 0.081(3) 0.131(5) 0.069(3) -0.001(3) -0.017(2) 0.009(3)
C13 0.086(4) 0.131(5) 0.067(3) -0.008(3) -0.005(3) -0.030(3)
C14 0.090(4) 0.129(5) 0.113(4) -0.061(4) -0.004(3) 0.003(3)
C15 0.072(3) 0.092(3) 0.097(3) -0.019(3) -0.014(2) 0.006(2)
C16 0.063(2) 0.071(3) 0.0408(18) 0.0024(17) 0.0115(15) 0.0065(18)
C17 0.061(2) 0.065(2) 0.0411(18) -0.0005(17) 0.0099(15) 0.0082(17)
C18 0.076(3) 0.106(3) 0.064(2) 0.021(2) 0.018(2) 0.001(2)
C19 0.0502(18) 0.062(2) 0.0414(17) -0.0055(18) 0.0094(14) -0.0002(17)
C20 0.061(2) 0.068(3) 0.065(2) 0.000(2) 0.0118(18) 0.0034(19)
C21 0.073(3) 0.097(4) 0.073(3) -0.007(3) 0.009(2) 0.022(3)
C22 0.063(3) 0.141(5) 0.066(3) -0.007(3) 0.013(2) 0.026(3)
C23 0.051(3) 0.163(6) 0.093(3) 0.019(3) 0.026(2) -0.019(3)
C24 0.077(3) 0.087(3) 0.079(3) 0.011(3) 0.017(2) -0.019(3)
C25 0.0547(19) 0.065(2) 0.0490(18) 0.0053(19) 0.0172(15) 0.0040(18)
C26 0.070(3) 0.092(3) 0.077(3) 0.012(3) 0.000(2) 0.009(2)
C27 0.074(3) 0.129(5) 0.090(4) 0.026(3) -0.009(2) 0.008(3)
C28 0.093(4) 0.130(5) 0.065(3) 0.008(3) 0.000(3) -0.026(3)
C29 0.149(5) 0.097(4) 0.077(3) -0.012(3) 0.012(3) -0.027(4)
C30 0.121(4) 0.080(3) 0.058(2) -0.001(2) 0.001(2) 0.006(3)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.438(3) . ?
S1 O2 1.450(3) . ?
S1 C4 1.766(3) . ?
S1 C2 1.800(3) . ?
S2 O5 1.427(3) . ?
S2 O6 1.448(3) . ?
S2 C19 1.753(3) . ?
S2 C17 1.800(3) . ?
O1 C1 1.409(4) . ?
O1 H1 0.8200 . ?
O4 C16 1.413(4) . ?
O4 H4 0.8200 . ?
C1 C10 1.520(4) . ?
C1 C2 1.542(4) . ?
C1 H1A 0.9800 . ?
C2 C3 1.510(5) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C9 1.378(5) . ?
C4 C5 1.380(5) . ?
C5 C6 1.372(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.358(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.366(5) . ?
C10 C15 1.367(5) . ?
C11 C12 1.386(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.335(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C25 1.514(4) . ?
C16 C17 1.533(5) . ?
C16 H16 0.9800 . ?
C17 C18 1.523(5) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.365(5) . ?
C19 C20 1.378(5) . ?
C20 C21 1.385(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.343(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.356(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C30 1.365(6) . ?
C25 C26 1.369(5) . ?
C26 C27 1.386(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.350(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.344(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.390(6) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 118.32(18) . . ?
O3 S1 C4 109.22(17) . . ?
O2 S1 C4 107.30(16) . . ?
O3 S1 C2 107.16(17) . . ?
O2 S1 C2 109.05(16) . . ?
C4 S1 C2 105.02(15) . . ?
O5 S2 O6 119.2(2) . . ?
O5 S2 C19 108.17(19) . . ?
O6 S2 C19 107.02(17) . . ?
O5 S2 C17 109.83(18) . . ?
O6 S2 C17 106.31(17) . . ?
C19 S2 C17 105.51(15) . . ?
C1 O1 H1 109.5 . . ?
C16 O4 H4 109.5 . . ?
O1 C1 C10 109.0(3) . . ?
O1 C1 C2 110.6(3) . . ?
C10 C1 C2 110.8(3) . . ?
O1 C1 H1A 108.8 . . ?
C10 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
C3 C2 C1 113.0(3) . . ?
C3 C2 S1 111.5(2) . . ?
C1 C2 S1 109.5(2) . . ?
C3 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
S1 C2 H2 107.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C4 C5 120.9(3) . . ?
C9 C4 S1 119.1(3) . . ?
C5 C4 S1 120.0(3) . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 120.3(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 118.5(4) . . ?
C4 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C15 117.9(4) . . ?
C11 C10 C1 121.5(4) . . ?
C15 C10 C1 120.5(3) . . ?
C10 C11 C12 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 121.4(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 118.9(4) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 119.9(5) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 121.0(4) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
O4 C16 C25 110.4(3) . . ?
O4 C16 C17 110.7(3) . . ?
C25 C16 C17 110.1(3) . . ?
O4 C16 H16 108.5 . . ?
C25 C16 H16 108.5 . . ?
C17 C16 H16 108.5 . . ?
C18 C17 C16 114.2(3) . . ?
C18 C17 S2 110.8(3) . . ?
C16 C17 S2 108.8(2) . . ?
C18 C17 H17 107.6 . . ?
C16 C17 H17 107.6 . . ?
S2 C17 H17 107.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 120.2(4) . . ?
C24 C19 S2 121.2(3) . . ?
C20 C19 S2 118.6(3) . . ?
C19 C20 C21 119.7(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 119.9(5) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.6(4) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 120.9(4) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C19 C24 C23 118.7(5) . . ?
C19 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C30 C25 C26 117.5(4) . . ?
C30 C25 C16 120.7(3) . . ?
C26 C25 C16 121.8(4) . . ?
C25 C26 C27 121.1(5) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C28 C27 C26 120.0(5) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 C27 120.2(5) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 119.8(5) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C25 C30 C29 121.3(4) . . ?
C25 C30 H30 119.3 . . ?
C29 C30 H30 119.3 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 50.3(4) . . . . ?
C10 C1 C2 C3 -70.7(4) . . . . ?
O1 C1 C2 S1 -74.7(3) . . . . ?
C10 C1 C2 S1 164.4(3) . . . . ?
O3 S1 C2 C3 175.4(3) . . . . ?
O2 S1 C2 C3 -55.5(3) . . . . ?
C4 S1 C2 C3 59.3(3) . . . . ?
O3 S1 C2 C1 -58.8(3) . . . . ?
O2 S1 C2 C1 70.4(3) . . . . ?
C4 S1 C2 C1 -174.9(3) . . . . ?
O3 S1 C4 C9 141.1(3) . . . . ?
O2 S1 C4 C9 11.7(3) . . . . ?
C2 S1 C4 C9 -104.3(3) . . . . ?
O3 S1 C4 C5 -38.2(3) . . . . ?
O2 S1 C4 C5 -167.6(3) . . . . ?
C2 S1 C4 C5 76.4(3) . . . . ?
C9 C4 C5 C6 1.4(5) . . . . ?
S1 C4 C5 C6 -179.3(3) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
C5 C6 C7 C8 -1.5(6) . . . . ?
C6 C7 C8 C9 1.7(6) . . . . ?
C5 C4 C9 C8 -1.2(5) . . . . ?
S1 C4 C9 C8 179.5(3) . . . . ?
C7 C8 C9 C4 -0.4(6) . . . . ?
O1 C1 C10 C11 -5.7(5) . . . . ?
C2 C1 C10 C11 116.2(4) . . . . ?
O1 C1 C10 C15 172.2(3) . . . . ?
C2 C1 C10 C15 -65.8(5) . . . . ?
C15 C10 C11 C12 1.5(6) . . . . ?
C1 C10 C11 C12 179.5(4) . . . . ?
C10 C11 C12 C13 -1.5(8) . . . . ?
C11 C12 C13 C14 0.8(8) . . . . ?
C12 C13 C14 C15 -0.2(8) . . . . ?
C11 C10 C15 C14 -0.9(7) . . . . ?
C1 C10 C15 C14 -178.9(4) . . . . ?
C13 C14 C15 C10 0.2(8) . . . . ?
O4 C16 C17 C18 55.8(4) . . . . ?
C25 C16 C17 C18 -66.6(4) . . . . ?
O4 C16 C17 S2 -68.6(3) . . . . ?
C25 C16 C17 S2 169.0(3) . . . . ?
O5 S2 C17 C18 -39.3(3) . . . . ?
O6 S2 C17 C18 -169.5(3) . . . . ?
C19 S2 C17 C18 77.1(3) . . . . ?
O5 S2 C17 C16 87.1(3) . . . . ?
O6 S2 C17 C16 -43.1(3) . . . . ?
C19 S2 C17 C16 -156.5(3) . . . . ?
O5 S2 C19 C24 26.3(3) . . . . ?
O6 S2 C19 C24 155.9(3) . . . . ?
C17 S2 C19 C24 -91.2(3) . . . . ?
O5 S2 C19 C20 -151.5(3) . . . . ?
O6 S2 C19 C20 -22.0(3) . . . . ?
C17 S2 C19 C20 91.0(3) . . . . ?
C24 C19 C20 C21 1.2(6) . . . . ?
S2 C19 C20 C21 179.1(3) . . . . ?
C19 C20 C21 C22 -0.5(6) . . . . ?
C20 C21 C22 C23 -0.8(7) . . . . ?
C21 C22 C23 C24 1.4(8) . . . . ?
C20 C19 C24 C23 -0.6(6) . . . . ?
S2 C19 C24 C23 -178.5(3) . . . . ?
C22 C23 C24 C19 -0.7(7) . . . . ?
O4 C16 C25 C30 159.8(3) . . . . ?
C17 C16 C25 C30 -77.6(4) . . . . ?
O4 C16 C25 C26 -19.5(5) . . . . ?
C17 C16 C25 C26 103.1(4) . . . . ?
C30 C25 C26 C27 1.4(6) . . . . ?
C16 C25 C26 C27 -179.3(4) . . . . ?
C25 C26 C27 C28 -0.9(7) . . . . ?
C26 C27 C28 C29 -1.1(9) . . . . ?
C27 C28 C29 C30 2.4(9) . . . . ?
C26 C25 C30 C29 0.0(6) . . . . ?
C16 C25 C30 C29 -179.3(4) . . . . ?
C28 C29 C30 C25 -1.9(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O6 0.82 1.96 2.777(4) 170.2 2_645
O4 H4 O2 0.82 2.08 2.871(3) 162.5 2_655

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.040