# 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

_publ_section_title              
;Diastereoselective r-vinyl butyrolactone synthesis
via gold catalyzed cyclization of allylic acetat
;
loop_
_publ_author_name
'Zili Chen'
'Ya-Hui Wang'
'Yu-Xin Zhang'
'Li-Li Zhu'
_publ_contact_author_name        'Zili Chen'
_publ_contact_author_email       ZILICHEN@RUC.EDU.CN

# Attachment 'cystal_data_for_8a.cif'

data_r90926f
_database_code_depnum_ccdc_archive 'CCDC 750019'
#TrackingRef 'cystal_data_for_8a.cif'

_chemical_absolute_configuration rm
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H29 N O6 S'
_chemical_formula_weight         471.55

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   11.814(2)
_cell_length_b                   5.9898(12)
_cell_length_c                   17.425(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.02(3)
_cell_angle_gamma                90.00
_cell_volume                     1185.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4214
_cell_measurement_theta_min      1.793
_cell_measurement_theta_max      27.912

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9654
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8646
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3921
_reflns_number_gt                3774
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'crystalclear(Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0473P)^2^+0.3851P] 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     SHELXL
_refine_ls_extinction_coef       0.047(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_number_reflns         3921
_refine_ls_number_parameters     301
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0904
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.004
_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 0.16411(4) 0.83575(10) 0.78980(3) 0.02401(16) Uani 1 1 d . . .
O1 O 0.26612(14) 0.6966(3) 0.81383(9) 0.0334(4) Uani 1 1 d . . .
O2 O 0.17285(15) 1.0716(3) 0.80363(10) 0.0338(4) Uani 1 1 d . . .
O3 O 0.25569(12) 0.3182(3) 0.66746(8) 0.0226(3) Uani 1 1 d . . .
O4 O 0.24280(16) 0.6187(3) 0.58843(11) 0.0388(5) Uani 1 1 d . . .
O5 O 0.59957(19) -0.0624(5) 0.85488(11) 0.0600(7) Uani 1 1 d . . .
O6 O 0.53306(18) 0.1499(4) 0.93617(10) 0.0546(6) Uani 1 1 d . . .
N1 N 0.11268(15) 0.8016(3) 0.69367(10) 0.0238(4) Uani 1 1 d . . .
C1 C -0.1975(3) 0.5036(5) 0.95127(17) 0.0434(7) Uani 1 1 d . . .
H1A H -0.1988 0.3434 0.9515 0.065 Uiso 1 1 calc R . .
H1B H -0.2739 0.5590 0.9231 0.065 Uiso 1 1 calc R . .
H1C H -0.1767 0.5577 1.0052 0.065 Uiso 1 1 calc R . .
C2 C -0.1078(2) 0.5834(4) 0.91029(13) 0.0295(5) Uani 1 1 d . . .
C3 C -0.1182(2) 0.7955(4) 0.87567(13) 0.0305(6) Uani 1 1 d . . .
H3 H -0.1813 0.8864 0.8774 0.037 Uiso 1 1 calc R . .
C4 C -0.03566(19) 0.8717(4) 0.83890(13) 0.0264(5) Uani 1 1 d . . .
H4 H -0.0429 1.0136 0.8164 0.032 Uiso 1 1 calc R . .
C5 C 0.05842(19) 0.7351(4) 0.83570(13) 0.0238(5) Uani 1 1 d . . .
C6 C 0.0703(2) 0.5223(4) 0.86923(13) 0.0275(5) Uani 1 1 d . . .
H6 H 0.1324 0.4301 0.8666 0.033 Uiso 1 1 calc R . .
C7 C -0.0133(2) 0.4506(5) 0.90696(13) 0.0318(6) Uani 1 1 d . . .
H7 H -0.0054 0.3099 0.9305 0.038 Uiso 1 1 calc R . .
C8 C 0.01536(19) 0.9431(5) 0.64731(14) 0.0322(6) Uani 1 1 d . . .
H8A H -0.0114 1.0440 0.6822 0.039 Uiso 1 1 calc R . .
H8B H 0.0402 1.0304 0.6080 0.039 Uiso 1 1 calc R . .
C9 C -0.0781(3) 0.7868(5) 0.60840(19) 0.0498(8) Uani 1 1 d . . .
H9A H -0.1287 0.8503 0.5597 0.060 Uiso 1 1 calc R . .
H9B H -0.1256 0.7468 0.6437 0.060 Uiso 1 1 calc R . .
C10 C -0.0111(2) 0.5843(5) 0.59015(16) 0.0429(7) Uani 1 1 d . . .
H10A H 0.0102 0.6056 0.5407 0.051 Uiso 1 1 calc R . .
H10B H -0.0581 0.4498 0.5859 0.051 Uiso 1 1 calc R . .
C11 C 0.10011(19) 0.5701(4) 0.66223(13) 0.0255(5) Uani 1 1 d . . .
H11 H 0.0883 0.4648 0.7024 0.031 Uiso 1 1 calc R . .
C12 C 0.20827(19) 0.5079(4) 0.63550(13) 0.0232(5) Uani 1 1 d . . .
C13 C 0.36511(18) 0.2468(4) 0.64949(12) 0.0227(5) Uani 1 1 d . . .
H13 H 0.4137 0.3775 0.6467 0.027 Uiso 1 1 calc R . .
C14 C 0.33560(18) 0.1242(4) 0.57161(13) 0.0233(5) Uani 1 1 d . . .
H14 H 0.2849 0.0025 0.5651 0.028 Uiso 1 1 calc R . .
C15 C 0.37825(18) 0.1807(4) 0.51145(13) 0.0229(5) Uani 1 1 d . . .
H15 H 0.4281 0.3037 0.5190 0.027 Uiso 1 1 calc R . .
C16 C 0.35376(18) 0.0661(4) 0.43352(13) 0.0225(5) Uani 1 1 d . . .
C17 C 0.30277(18) -0.1454(4) 0.42008(13) 0.0245(5) Uani 1 1 d . . .
H17 H 0.2874 -0.2238 0.4622 0.029 Uiso 1 1 calc R . .
C18 C 0.2748(2) -0.2400(4) 0.34442(14) 0.0286(5) Uani 1 1 d . . .
H18 H 0.2408 -0.3812 0.3361 0.034 Uiso 1 1 calc R . .
C19 C 0.2973(2) -0.1242(4) 0.28096(14) 0.0318(6) Uani 1 1 d . . .
H19 H 0.2764 -0.1863 0.2301 0.038 Uiso 1 1 calc R . .
C20 C 0.3509(2) 0.0833(4) 0.29344(14) 0.0318(6) Uani 1 1 d . . .
H20 H 0.3671 0.1601 0.2513 0.038 Uiso 1 1 calc R . .
C21 C 0.3805(2) 0.1762(4) 0.37004(14) 0.0283(5) Uani 1 1 d . . .
H21 H 0.4186 0.3136 0.3789 0.034 Uiso 1 1 calc R . .
C22 C 0.4286(2) 0.0982(4) 0.71876(13) 0.0277(5) Uani 1 1 d . . .
H22A H 0.3816 -0.0345 0.7189 0.033 Uiso 1 1 calc R . .
H22B H 0.5030 0.0510 0.7107 0.033 Uiso 1 1 calc R . .
C23 C 0.4519(2) 0.2125(5) 0.79937(13) 0.0299(5) Uani 1 1 d . . .
H23A H 0.4847 0.3595 0.7961 0.036 Uiso 1 1 calc R . .
H23B H 0.3780 0.2316 0.8127 0.036 Uiso 1 1 calc R . .
C24 C 0.5351(2) 0.0820(5) 0.86413(14) 0.0346(6) Uani 1 1 d . . .
C25 C 0.6137(3) 0.0437(7) 1.00351(16) 0.0671(11) Uani 1 1 d . . .
H25A H 0.6003 -0.1145 1.0008 0.101 Uiso 1 1 calc R . .
H25B H 0.6014 0.1010 1.0520 0.101 Uiso 1 1 calc R . .
H25C H 0.6931 0.0739 1.0026 0.101 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 0.0234(3) 0.0264(3) 0.0218(3) -0.0031(2) 0.00546(19) -0.0004(2)
O1 0.0223(8) 0.0468(11) 0.0278(9) 0.0003(8) 0.0014(7) 0.0072(8)
O2 0.0419(10) 0.0275(10) 0.0360(9) -0.0102(8) 0.0174(8) -0.0094(8)
O3 0.0209(7) 0.0264(9) 0.0225(7) 0.0032(7) 0.0092(6) 0.0014(7)
O4 0.0518(11) 0.0283(10) 0.0478(10) 0.0087(9) 0.0329(9) 0.0059(8)
O5 0.0549(12) 0.0898(18) 0.0318(10) 0.0105(11) 0.0057(9) 0.0368(13)
O6 0.0559(12) 0.0843(17) 0.0183(9) -0.0039(10) 0.0014(8) 0.0105(12)
N1 0.0238(9) 0.0260(11) 0.0209(9) -0.0020(8) 0.0052(7) 0.0037(8)
C1 0.0484(16) 0.0479(19) 0.0375(14) 0.0029(13) 0.0177(13) -0.0120(13)
C2 0.0326(12) 0.0334(14) 0.0219(11) -0.0042(11) 0.0065(10) -0.0079(11)
C3 0.0294(11) 0.0352(16) 0.0271(11) -0.0013(11) 0.0085(9) 0.0035(11)
C4 0.0305(11) 0.0242(13) 0.0247(11) 0.0021(10) 0.0079(9) 0.0026(10)
C5 0.0268(11) 0.0248(12) 0.0190(10) -0.0034(9) 0.0051(9) -0.0032(9)
C6 0.0351(13) 0.0243(13) 0.0204(11) -0.0017(9) 0.0033(10) 0.0038(10)
C7 0.0436(14) 0.0281(13) 0.0226(11) 0.0012(11) 0.0070(10) -0.0065(12)
C8 0.0268(12) 0.0378(14) 0.0292(12) 0.0034(12) 0.0031(10) 0.0093(11)
C9 0.0412(15) 0.045(2) 0.0537(17) 0.0050(15) -0.0019(13) -0.0002(13)
C10 0.0257(12) 0.064(2) 0.0352(14) -0.0235(14) 0.0016(11) -0.0044(13)
C11 0.0248(11) 0.0262(13) 0.0269(11) -0.0050(10) 0.0093(9) -0.0019(10)
C12 0.0247(11) 0.0234(13) 0.0216(11) -0.0023(9) 0.0068(9) -0.0030(9)
C13 0.0171(10) 0.0290(12) 0.0234(11) -0.0008(9) 0.0078(8) 0.0002(9)
C14 0.0198(11) 0.0269(13) 0.0224(11) -0.0002(10) 0.0044(9) -0.0007(9)
C15 0.0187(10) 0.0243(12) 0.0255(11) 0.0012(9) 0.0061(9) -0.0005(9)
C16 0.0176(10) 0.0280(13) 0.0231(11) 0.0049(10) 0.0079(8) 0.0035(9)
C17 0.0227(10) 0.0273(12) 0.0247(10) 0.0034(11) 0.0085(8) 0.0042(10)
C18 0.0229(11) 0.0314(14) 0.0311(12) -0.0043(10) 0.0066(9) 0.0010(9)
C19 0.0289(12) 0.0431(17) 0.0233(11) -0.0040(11) 0.0069(9) 0.0066(11)
C20 0.0361(13) 0.0387(15) 0.0231(11) 0.0050(11) 0.0124(10) 0.0073(12)
C21 0.0304(12) 0.0289(13) 0.0288(12) 0.0025(11) 0.0135(10) 0.0029(10)
C22 0.0225(11) 0.0379(14) 0.0231(11) 0.0038(11) 0.0067(9) 0.0031(10)
C23 0.0237(11) 0.0438(15) 0.0220(11) -0.0001(11) 0.0058(9) 0.0019(11)
C24 0.0236(12) 0.0572(18) 0.0243(12) -0.0007(12) 0.0085(10) -0.0031(12)
C25 0.062(2) 0.107(3) 0.0215(13) 0.0151(17) -0.0064(13) -0.006(2)

_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 O1 1.4296(17) . ?
S1 O2 1.4323(18) . ?
S1 N1 1.6295(18) . ?
S1 C5 1.764(2) . ?
O3 C12 1.320(3) . ?
O3 C13 1.475(2) . ?
O4 C12 1.210(3) . ?
O5 C24 1.193(3) . ?
O6 C24 1.326(3) . ?
O6 C25 1.439(4) . ?
N1 C8 1.477(3) . ?
N1 C11 1.483(3) . ?
C1 C2 1.510(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.384(4) . ?
C2 C3 1.398(4) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C6 C7 1.397(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.463(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.529(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.549(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.522(3) . ?
C11 H11 0.9800 . ?
C13 C14 1.497(3) . ?
C13 C22 1.521(3) . ?
C13 H13 0.9800 . ?
C14 C15 1.326(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.477(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.395(3) . ?
C16 C21 1.397(3) . ?
C17 C18 1.389(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.392(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.398(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.518(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.496(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
O1 S1 O2 120.66(11) . . ?
O1 S1 N1 105.85(10) . . ?
O2 S1 N1 106.61(10) . . ?
O1 S1 C5 108.24(11) . . ?
O2 S1 C5 106.73(11) . . ?
N1 S1 C5 108.27(10) . . ?
C12 O3 C13 117.04(16) . . ?
C24 O6 C25 117.1(3) . . ?
C8 N1 C11 110.55(18) . . ?
C8 N1 S1 120.23(15) . . ?
C11 N1 S1 117.90(15) . . ?
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 118.7(2) . . ?
C7 C2 C1 121.1(2) . . ?
C3 C2 C1 120.1(2) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 S1 120.06(18) . . ?
C4 C5 S1 119.31(18) . . ?
C5 C6 C7 118.5(2) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C2 C7 C6 121.7(2) . . ?
C2 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C9 C8 N1 105.1(2) . . ?
C9 C8 H8A 110.7 . . ?
N1 C8 H8A 110.7 . . ?
C9 C8 H8B 110.7 . . ?
N1 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C8 C9 C10 103.7(2) . . ?
C8 C9 H9A 111.0 . . ?
C10 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
C10 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C9 C10 C11 104.3(2) . . ?
C9 C10 H10A 110.9 . . ?
C11 C10 H10A 110.9 . . ?
C9 C10 H10B 110.9 . . ?
C11 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
N1 C11 C12 109.58(18) . . ?
N1 C11 C10 102.96(19) . . ?
C12 C11 C10 111.17(19) . . ?
N1 C11 H11 111.0 . . ?
C12 C11 H11 111.0 . . ?
C10 C11 H11 111.0 . . ?
O4 C12 O3 125.1(2) . . ?
O4 C12 C11 122.8(2) . . ?
O3 C12 C11 112.10(18) . . ?
O3 C13 C14 109.64(17) . . ?
O3 C13 C22 105.69(17) . . ?
C14 C13 C22 111.87(19) . . ?
O3 C13 H13 109.9 . . ?
C14 C13 H13 109.9 . . ?
C22 C13 H13 109.9 . . ?
C15 C14 C13 123.2(2) . . ?
C15 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
C14 C15 C16 126.0(2) . . ?
C14 C15 H15 117.0 . . ?
C16 C15 H15 117.0 . . ?
C17 C16 C21 118.5(2) . . ?
C17 C16 C15 122.8(2) . . ?
C21 C16 C15 118.6(2) . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.4(2) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C16 C21 C20 121.1(2) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C13 113.2(2) . . ?
C23 C22 H22A 108.9 . . ?
C13 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C13 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C24 C23 C22 112.1(2) . . ?
C24 C23 H23A 109.2 . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C22 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
O5 C24 O6 122.0(2) . . ?
O5 C24 C23 126.0(2) . . ?
O6 C24 C23 112.0(2) . . ?
O6 C25 H25A 109.5 . . ?
O6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
_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 S1 N1 C8 -172.27(18) . . . . ?
O2 S1 N1 C8 -42.6(2) . . . . ?
C5 S1 N1 C8 71.86(19) . . . . ?
O1 S1 N1 C11 47.53(18) . . . . ?
O2 S1 N1 C11 177.15(16) . . . . ?
C5 S1 N1 C11 -68.34(18) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 C4 179.1(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C3 C4 C5 S1 -179.18(17) . . . . ?
O1 S1 C5 C6 -15.5(2) . . . . ?
O2 S1 C5 C6 -146.82(18) . . . . ?
N1 S1 C5 C6 98.75(19) . . . . ?
O1 S1 C5 C4 163.61(17) . . . . ?
O2 S1 C5 C4 32.3(2) . . . . ?
N1 S1 C5 C4 -82.09(19) . . . . ?
C4 C5 C6 C7 -0.9(3) . . . . ?
S1 C5 C6 C7 178.29(17) . . . . ?
C3 C2 C7 C6 -0.8(3) . . . . ?
C1 C2 C7 C6 180.0(2) . . . . ?
C5 C6 C7 C2 1.3(3) . . . . ?
C11 N1 C8 C9 20.6(3) . . . . ?
S1 N1 C8 C9 -122.3(2) . . . . ?
N1 C8 C9 C10 -34.5(3) . . . . ?
C8 C9 C10 C11 36.0(3) . . . . ?
C8 N1 C11 C12 120.5(2) . . . . ?
S1 N1 C11 C12 -95.65(19) . . . . ?
C8 N1 C11 C10 2.2(2) . . . . ?
S1 N1 C11 C10 145.97(16) . . . . ?
C9 C10 C11 N1 -23.0(3) . . . . ?
C9 C10 C11 C12 -140.3(2) . . . . ?
C13 O3 C12 O4 5.5(3) . . . . ?
C13 O3 C12 C11 -176.68(17) . . . . ?
N1 C11 C12 O4 -54.3(3) . . . . ?
C10 C11 C12 O4 58.8(3) . . . . ?
N1 C11 C12 O3 127.81(19) . . . . ?
C10 C11 C12 O3 -119.0(2) . . . . ?
C12 O3 C13 C14 -84.6(2) . . . . ?
C12 O3 C13 C22 154.63(18) . . . . ?
O3 C13 C14 C15 125.4(2) . . . . ?
C22 C13 C14 C15 -117.7(2) . . . . ?
C13 C14 C15 C16 179.4(2) . . . . ?
C14 C15 C16 C17 -14.5(4) . . . . ?
C14 C15 C16 C21 164.1(2) . . . . ?
C21 C16 C17 C18 -2.7(3) . . . . ?
C15 C16 C17 C18 175.9(2) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 1.9(3) . . . . ?
C18 C19 C20 C21 -0.9(3) . . . . ?
C17 C16 C21 C20 3.7(3) . . . . ?
C15 C16 C21 C20 -175.0(2) . . . . ?
C19 C20 C21 C16 -1.9(3) . . . . ?
O3 C13 C22 C23 -56.5(2) . . . . ?
C14 C13 C22 C23 -175.81(19) . . . . ?
C13 C22 C23 C24 -168.27(19) . . . . ?
C25 O6 C24 O5 0.9(4) . . . . ?
C25 O6 C24 C23 -177.1(3) . . . . ?
C22 C23 C24 O5 17.7(4) . . . . ?
C22 C23 C24 O6 -164.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.040