Supplementary Material (ESI) for Organic and Biomolecular Chemistry
This journal is (C) The Royal Society of Chemistry 2006


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Steven V. Ley'
_publ_contact_author_address     
;
Department of Chemistry
University of Cambridge
Lensfield Road,
Cambridge CB2 1EW, U.K.
;

_publ_contact_author_email       svl1000@cam.ac.uk

_publ_section_title              
;
;
loop_
_publ_author_name
'Steven V. Ley'
'Lech-Gustav Milroy'
'Giovanna Zinzalla'

data_sl0410
_database_code_depnum_ccdc_archive 'CCDC 600002'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H30 O4 S2'
_chemical_formula_sum            'C21 H30 O4 S2'
_chemical_formula_weight         410.57
_chemical_absolute_configuration 
'the absolute configuration was determined reliably'
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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a                   8.1371(1)
_cell_length_b                   9.7341(1)
_cell_length_c                   26.6319(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2109.44(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    15429
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_special_details           
;
The -OH hydrogen atom was located in the final difference map and its
position was refined satisfactorily.
;
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'

#Crystallographic CIF of compound 1c
_diffrn_reflns_number            17628
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4759
_reflns_number_gt                4144
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_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^)+(0.0414P)^2^+0.2841P] 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    mixed
_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   0.00(6)
_refine_ls_number_reflns         4759
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0821
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.005
_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
O1 O 1.01143(15) 1.18831(12) 0.57171(4) 0.0275(3) Uani 1 1 d . . .
C2 C 1.0872(2) 1.30664(18) 0.59532(7) 0.0306(4) Uani 1 1 d . . .
H2 H 1.1278 1.2808 0.6295 0.037 Uiso 1 1 calc R . .
C3 C 1.2294(2) 1.3564(2) 0.56357(7) 0.0404(5) Uani 1 1 d . . .
H3A H 1.2844 1.4345 0.5805 0.048 Uiso 1 1 calc R . .
H3B H 1.1881 1.3888 0.5307 0.048 Uiso 1 1 calc R . .
C4 C 1.3525(2) 1.2398(2) 0.55564(7) 0.0404(5) Uani 1 1 d . . .
H4A H 1.4392 1.2699 0.5320 0.049 Uiso 1 1 calc R . .
H4B H 1.4054 1.2165 0.5880 0.049 Uiso 1 1 calc R . .
C5 C 1.2662(2) 1.1137(2) 0.53471(7) 0.0343(4) Uani 1 1 d . . .
H5A H 1.3445 1.0359 0.5337 0.041 Uiso 1 1 calc R . .
H5B H 1.2301 1.1326 0.4999 0.041 Uiso 1 1 calc R . .
C6 C 1.1175(2) 1.07348(19) 0.56629(6) 0.0284(4) Uani 1 1 d . . .
O7 O 1.18152(14) 1.03234(12) 0.61377(4) 0.0282(3) Uani 1 1 d . . .
C8 C 1.0576(2) 0.98736(19) 0.64877(6) 0.0277(4) Uani 1 1 d . . .
H8 H 0.9747 1.0622 0.6531 0.033 Uiso 1 1 calc R . .
C9 C 0.9725(2) 0.86104(18) 0.62829(6) 0.0292(4) Uani 1 1 d . . .
H9A H 0.8897 0.8283 0.6528 0.035 Uiso 1 1 calc R . .
H9B H 1.0540 0.7868 0.6232 0.035 Uiso 1 1 calc R . .
C10 C 0.8877(2) 0.89456(18) 0.57799(6) 0.0287(4) Uani 1 1 d . . .
C11 C 1.0150(2) 0.95967(18) 0.54272(6) 0.0287(4) Uani 1 1 d . . .
H11A H 1.0900 0.8867 0.5306 0.034 Uiso 1 1 calc R . .
H11B H 0.9570 0.9975 0.5131 0.034 Uiso 1 1 calc R . .
S12 S 0.82009(6) 0.73934(5) 0.545487(18) 0.03787(13) Uani 1 1 d . . .
C13 C 0.6605(3) 0.6760(2) 0.58668(8) 0.0414(4) Uani 1 1 d . . .
H13A H 0.6171 0.5889 0.5728 0.050 Uiso 1 1 calc R . .
H13B H 0.7095 0.6554 0.6199 0.050 Uiso 1 1 calc R . .
C14 C 0.5180(2) 0.7758(2) 0.59396(8) 0.0444(5) Uani 1 1 d . . .
H14A H 0.4710 0.7990 0.5607 0.053 Uiso 1 1 calc R . .
H14B H 0.4310 0.7301 0.6139 0.053 Uiso 1 1 calc R . .
C15 C 0.5688(2) 0.9077(2) 0.62038(7) 0.0382(4) Uani 1 1 d . . .
H15A H 0.6181 0.8836 0.6532 0.046 Uiso 1 1 calc R . .
H15B H 0.4690 0.9629 0.6271 0.046 Uiso 1 1 calc R . .
S16 S 0.71361(5) 1.01282(5) 0.585909(16) 0.03116(11) Uani 1 1 d . . .
C17 C 0.9481(2) 1.4090(2) 0.60013(7) 0.0379(5) Uani 1 1 d . . .
H17A H 0.9880 1.4914 0.6182 0.045 Uiso 1 1 calc R . .
H17B H 0.9123 1.4379 0.5662 0.045 Uiso 1 1 calc R . .
O18 O 0.81167(18) 1.35223(16) 0.62650(6) 0.0492(4) Uani 1 1 d D . .
H18 H 0.791(3) 1.2633(18) 0.6140(8) 0.059 Uiso 1 1 d D . .
C19 C 1.1436(2) 0.9635(2) 0.69824(6) 0.0340(4) Uani 1 1 d . . .
H19A H 1.0762 0.9034 0.7200 0.041 Uiso 1 1 calc R . .
H19B H 1.2512 0.9187 0.6926 0.041 Uiso 1 1 calc R . .
O20 O 1.16570(17) 1.09355(16) 0.72116(5) 0.0451(4) Uani 1 1 d . . .
C21 C 1.2439(3) 1.0868(3) 0.76868(8) 0.0582(7) Uani 1 1 d . . .
H21A H 1.2020 1.0055 0.7870 0.070 Uiso 1 1 calc R . .
H21B H 1.2137 1.1694 0.7883 0.070 Uiso 1 1 calc R . .
C22 C 1.4290(2) 1.0778(2) 0.76575(7) 0.0380(5) Uani 1 1 d . . .
C23 C 1.5149(3) 1.1476(3) 0.72976(9) 0.0572(6) Uani 1 1 d . . .
H23 H 1.4571 1.1976 0.7047 0.069 Uiso 1 1 calc R . .
C24 C 1.6828(4) 1.1463(3) 0.72933(10) 0.0683(8) Uani 1 1 d . . .
H24 H 1.7408 1.1948 0.7039 0.082 Uiso 1 1 calc R . .
C25 C 1.7660(3) 1.0770(3) 0.76451(11) 0.0702(9) Uani 1 1 d . . .
H25 H 1.8828 1.0777 0.7642 0.084 Uiso 1 1 calc R . .
C26 C 1.6842(3) 1.0053(3) 0.80080(10) 0.0740(8) Uani 1 1 d . . .
H26 H 1.7438 0.9558 0.8256 0.089 Uiso 1 1 calc R . .
C27 C 1.5127(3) 1.0052(3) 0.80135(8) 0.0555(6) Uani 1 1 d . . .
H27 H 1.4547 0.9550 0.8263 0.067 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
O1 0.0283(6) 0.0266(6) 0.0276(6) 0.0004(5) -0.0002(5) 0.0044(5)
C2 0.0327(9) 0.0293(9) 0.0298(9) 0.0007(7) -0.0006(7) 0.0006(8)
C3 0.0429(11) 0.0368(10) 0.0413(10) 0.0051(8) 0.0041(9) -0.0044(9)
C4 0.0332(10) 0.0457(11) 0.0424(11) 0.0085(9) 0.0103(8) -0.0019(9)
C5 0.0318(10) 0.0403(10) 0.0308(9) 0.0051(8) 0.0069(7) 0.0070(8)
C6 0.0272(9) 0.0317(9) 0.0262(8) 0.0029(7) 0.0018(7) 0.0076(7)
O7 0.0226(6) 0.0358(7) 0.0261(6) 0.0061(5) 0.0005(5) 0.0040(5)
C8 0.0226(8) 0.0357(9) 0.0248(8) 0.0050(7) 0.0015(6) 0.0049(8)
C9 0.0266(9) 0.0306(9) 0.0305(9) 0.0056(7) -0.0004(7) 0.0026(7)
C10 0.0294(9) 0.0282(9) 0.0284(9) -0.0006(7) -0.0018(7) 0.0026(7)
C11 0.0308(9) 0.0307(9) 0.0244(8) 0.0002(7) 0.0022(7) 0.0071(7)
S12 0.0447(3) 0.0325(2) 0.0364(2) -0.0057(2) -0.0007(2) -0.0015(2)
C13 0.0427(11) 0.0370(10) 0.0445(10) 0.0009(9) -0.0058(9) -0.0073(9)
C14 0.0333(10) 0.0466(12) 0.0533(12) 0.0045(10) -0.0059(9) -0.0071(9)
C15 0.0256(9) 0.0467(12) 0.0422(10) 0.0045(9) 0.0010(8) 0.0030(9)
S16 0.0255(2) 0.0343(2) 0.0337(2) 0.00116(19) -0.00192(17) 0.00543(18)
C17 0.0442(11) 0.0294(10) 0.0400(11) -0.0030(8) 0.0017(9) 0.0053(9)
O18 0.0431(8) 0.0432(8) 0.0614(9) -0.0086(7) 0.0145(7) 0.0087(7)
C19 0.0280(10) 0.0454(12) 0.0285(9) 0.0048(8) -0.0022(7) 0.0030(8)
O20 0.0388(8) 0.0579(9) 0.0384(7) -0.0113(6) -0.0123(6) 0.0079(7)
C21 0.0391(12) 0.099(2) 0.0365(11) -0.0135(12) -0.0069(9) 0.0060(13)
C22 0.0301(10) 0.0498(12) 0.0341(10) -0.0114(9) -0.0029(8) -0.0004(9)
C23 0.0598(15) 0.0684(17) 0.0434(12) 0.0106(11) 0.0005(12) 0.0005(13)
C24 0.0723(19) 0.0803(19) 0.0524(14) -0.0065(13) 0.0186(14) -0.0267(17)
C25 0.0261(11) 0.109(2) 0.0755(18) -0.0360(17) 0.0040(12) -0.0038(13)
C26 0.0559(16) 0.099(2) 0.0672(16) 0.0142(16) -0.0163(13) 0.0234(18)
C27 0.0507(13) 0.0636(15) 0.0522(13) 0.0167(12) 0.0040(10) 0.0022(13)
_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
O1 C6 1.419(2) . ?
O1 C2 1.450(2) . ?
C2 C3 1.513(3) . ?
C2 C17 1.513(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.528(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.521(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.524(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O7 1.425(2) . ?
C6 C11 1.522(3) . ?
O7 C8 1.4411(19) . ?
C8 C19 1.509(2) . ?
C8 C9 1.513(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.542(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.535(2) . ?
C10 S12 1.8263(18) . ?
C10 S16 1.8378(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
S12 C13 1.808(2) . ?
C13 C14 1.525(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.521(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 S16 1.811(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 O18 1.425(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
O18 H18 0.942(16) . ?
C19 O20 1.417(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
O20 C21 1.418(3) . ?
C21 C22 1.511(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.365(3) . ?
C22 C23 1.367(3) . ?
C23 C24 1.367(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.338(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.365(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.396(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
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
C6 O1 C2 114.29(13) . . ?
O1 C2 C3 109.71(14) . . ?
O1 C2 C17 104.00(14) . . ?
C3 C2 C17 114.12(15) . . ?
O1 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
C17 C2 H2 109.6 . . ?
C2 C3 C4 109.91(16) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 110.36(15) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 111.81(15) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
O1 C6 O7 110.70(13) . . ?
O1 C6 C11 106.39(13) . . ?
O7 C6 C11 111.21(14) . . ?
O1 C6 C5 109.66(14) . . ?
O7 C6 C5 105.75(14) . . ?
C11 C6 C5 113.19(14) . . ?
C6 O7 C8 113.80(12) . . ?
O7 C8 C19 106.69(13) . . ?
O7 C8 C9 109.51(13) . . ?
C19 C8 C9 113.68(15) . . ?
O7 C8 H8 109.0 . . ?
C19 C8 H8 109.0 . . ?
C9 C8 H8 109.0 . . ?
C8 C9 C10 110.25(14) . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 108.49(14) . . ?
C11 C10 S12 104.77(11) . . ?
C9 C10 S12 111.82(12) . . ?
C11 C10 S16 109.38(11) . . ?
C9 C10 S16 112.20(12) . . ?
S12 C10 S16 109.89(9) . . ?
C6 C11 C10 114.69(14) . . ?
C6 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C6 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C13 S12 C10 102.18(9) . . ?
C14 C13 S12 113.96(14) . . ?
C14 C13 H13A 108.8 . . ?
S12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
S12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 112.92(16) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 S16 114.80(14) . . ?
C14 C15 H15A 108.6 . . ?
S16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
S16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C15 S16 C10 101.88(9) . . ?
O18 C17 C2 111.67(15) . . ?
O18 C17 H17A 109.3 . . ?
C2 C17 H17A 109.3 . . ?
O18 C17 H17B 109.3 . . ?
C2 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C17 O18 H18 108.6(15) . . ?
O20 C19 C8 107.31(15) . . ?
O20 C19 H19A 110.3 . . ?
C8 C19 H19A 110.3 . . ?
O20 C19 H19B 110.3 . . ?
C8 C19 H19B 110.3 . . ?
H19A C19 H19B 108.5 . . ?
C19 O20 C21 113.60(18) . . ?
O20 C21 C22 113.83(18) . . ?
O20 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
O20 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C27 C22 C23 119.3(2) . . ?
C27 C22 C21 119.5(2) . . ?
C23 C22 C21 121.1(2) . . ?
C22 C23 C24 120.8(2) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.4(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C27 119.7(2) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C22 C27 C26 119.4(2) . . ?
C22 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
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
C6 O1 C2 C3 61.59(18) . . . . ?
C6 O1 C2 C17 -175.96(13) . . . . ?
O1 C2 C3 C4 -56.7(2) . . . . ?
C17 C2 C3 C4 -172.91(16) . . . . ?
C2 C3 C4 C5 53.4(2) . . . . ?
C3 C4 C5 C6 -52.1(2) . . . . ?
C2 O1 C6 O7 57.16(18) . . . . ?
C2 O1 C6 C11 178.11(12) . . . . ?
C2 O1 C6 C5 -59.14(18) . . . . ?
C4 C5 C6 O1 53.71(19) . . . . ?
C4 C5 C6 O7 -65.68(18) . . . . ?
C4 C5 C6 C11 172.34(15) . . . . ?
O1 C6 O7 C8 62.57(18) . . . . ?
C11 C6 O7 C8 -55.48(18) . . . . ?
C5 C6 O7 C8 -178.73(14) . . . . ?
C6 O7 C8 C19 -173.71(14) . . . . ?
C6 O7 C8 C9 62.85(17) . . . . ?
O7 C8 C9 C10 -60.99(17) . . . . ?
C19 C8 C9 C10 179.79(14) . . . . ?
C8 C9 C10 C11 53.16(18) . . . . ?
C8 C9 C10 S12 168.21(12) . . . . ?
C8 C9 C10 S16 -67.79(16) . . . . ?
O1 C6 C11 C10 -72.30(17) . . . . ?
O7 C6 C11 C10 48.32(18) . . . . ?
C5 C6 C11 C10 167.20(14) . . . . ?
C9 C10 C11 C6 -47.53(19) . . . . ?
S12 C10 C11 C6 -167.09(12) . . . . ?
S16 C10 C11 C6 75.15(15) . . . . ?
C11 C10 S12 C13 -175.82(11) . . . . ?
C9 C10 S12 C13 66.88(14) . . . . ?
S16 C10 S12 C13 -58.41(11) . . . . ?
C10 S12 C13 C14 60.22(16) . . . . ?
S12 C13 C14 C15 -64.6(2) . . . . ?
C13 C14 C15 S16 64.3(2) . . . . ?
C14 C15 S16 C10 -58.94(15) . . . . ?
C11 C10 S16 C15 172.07(12) . . . . ?
C9 C10 S16 C15 -67.50(14) . . . . ?
S12 C10 S16 C15 57.57(11) . . . . ?
O1 C2 C17 O18 55.19(19) . . . . ?
C3 C2 C17 O18 174.69(15) . . . . ?
O7 C8 C19 O20 79.47(17) . . . . ?
C9 C8 C19 O20 -159.72(15) . . . . ?
C8 C19 O20 C21 179.26(15) . . . . ?
C19 O20 C21 C22 82.5(3) . . . . ?
O20 C21 C22 C27 -147.1(2) . . . . ?
O20 C21 C22 C23 36.6(4) . . . . ?
C27 C22 C23 C24 -0.6(4) . . . . ?
C21 C22 C23 C24 175.7(3) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C26 0.9(4) . . . . ?
C24 C25 C26 C27 -0.4(5) . . . . ?
C23 C22 C27 C26 1.0(4) . . . . ?
C21 C22 C27 C26 -175.3(3) . . . . ?
C25 C26 C27 C22 -0.5(5) . . . . ?
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044

# Attachment 'Crystallographic CIF of compound 1a.doc'

#Crystallographic CIF of compound 1a

Data_sl0409
_database_code_depnum_ccdc_archive 'CCDC 600003'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H30 O4 S2'
_chemical_formula_sum            'C21 H30 O4 S2'
_chemical_formula_weight         410.57
_chemical_absolute_configuration 
'the absolute configuration was determined reliably'
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           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a                   8.18360(10)
_cell_length_b                   11.8557(2)
_cell_length_c                   21.3327(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2069.75(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    14347
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_special_details           
;
The -OH hydrogen atom was located in the final difference map and its
position was refined successfully.
;
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073

#Crystallographic CIF of compound 1a
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_reflns_number            13637
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4721
_reflns_number_gt                4478
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_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^)+(0.0448P)^2^+0.8415P] 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    mixed
_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   -0.01(6)
_refine_ls_number_reflns         4721
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_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
O1 O 0.59710(16) 0.73735(11) 0.63060(6) 0.0229(3) Uani 1 1 d . . .
C2 C 0.5998(3) 0.75537(18) 0.56388(9) 0.0286(4) Uani 1 1 d . . .
H2 H 0.4853 0.7652 0.5484 0.034 Uiso 1 1 calc R . .
C3 C 0.6787(3) 0.6570(2) 0.52969(10) 0.0349(5) Uani 1 1 d . . .
H3A H 0.7963 0.6536 0.5404 0.042 Uiso 1 1 calc R . .
H3B H 0.6691 0.6686 0.4839 0.042 Uiso 1 1 calc R . .
C4 C 0.5963(3) 0.54601(19) 0.54789(9) 0.0321(5) Uani 1 1 d . . .
H4A H 0.4827 0.5450 0.5319 0.039 Uiso 1 1 calc R . .
H4B H 0.6561 0.4820 0.5288 0.039 Uiso 1 1 calc R . .
C5 C 0.5953(3) 0.53362(17) 0.61912(9) 0.0266(4) Uani 1 1 d . . .
H5A H 0.7090 0.5242 0.6342 0.032 Uiso 1 1 calc R . .
H5B H 0.5334 0.4649 0.6306 0.032 Uiso 1 1 calc R . .
C6 C 0.5187(2) 0.63555(16) 0.65151(8) 0.0211(3) Uani 1 1 d . . .
O7 O 0.56030(15) 0.62341(11) 0.71485(6) 0.0222(3) Uani 1 1 d . . .
C8 C 0.4881(2) 0.70318(15) 0.75785(8) 0.0195(3) Uani 1 1 d . . .
H8 H 0.5236 0.7815 0.7471 0.023 Uiso 1 1 calc R . .
C9 C 0.3027(2) 0.69455(16) 0.75527(8) 0.0213(4) Uani 1 1 d . . .
H9A H 0.2539 0.7495 0.7848 0.026 Uiso 1 1 calc R . .
H9B H 0.2683 0.6180 0.7683 0.026 Uiso 1 1 calc R . .
C10 C 0.2411(2) 0.71842(14) 0.68870(8) 0.0195(3) Uani 1 1 d . . .
C11 C 0.3327(2) 0.64070(17) 0.64266(8) 0.0224(4) Uani 1 1 d . . .
H11A H 0.2882 0.5634 0.6469 0.027 Uiso 1 1 calc R . .
H11B H 0.3095 0.6665 0.5994 0.027 Uiso 1 1 calc R . .
S12 S 0.02635(6) 0.67991(4) 0.67898(2) 0.02673(12) Uani 1 1 d . . .
C13 C -0.0738(2) 0.77837(18) 0.73129(11) 0.0316(4) Uani 1 1 d . . .
H13A H -0.1930 0.7643 0.7301 0.038 Uiso 1 1 calc R . .
H13B H -0.0360 0.7638 0.7746 0.038 Uiso 1 1 calc R . .
C14 C -0.0426(3) 0.90131(18) 0.71564(12) 0.0346(5) Uani 1 1 d . . .
H14A H -0.0804 0.9159 0.6723 0.042 Uiso 1 1 calc R . .
H14B H -0.1086 0.9489 0.7441 0.042 Uiso 1 1 calc R . .
C15 C 0.1350(3) 0.93640(17) 0.72092(11) 0.0307(4) Uani 1 1 d . . .
H15A H 0.1729 0.9209 0.7641 0.037 Uiso 1 1 calc R . .
H15B H 0.1424 1.0188 0.7140 0.037 Uiso 1 1 calc R . .
S16 S 0.27167(6) 0.86631(4) 0.66633(2) 0.02418(11) Uani 1 1 d . . .
C17 C 0.6925(3) 0.86454(19) 0.55507(11) 0.0386(5) Uani 1 1 d . . .
H17A H 0.8070 0.8538 0.5688 0.046 Uiso 1 1 calc R . .
H17B H 0.6940 0.8841 0.5100 0.046 Uiso 1 1 calc R . .
O18 O 0.6230(3) 0.95453(17) 0.58903(11) 0.0659(6) Uani 1 1 d D . .
H18 H 0.542(4) 0.919(3) 0.6203(14) 0.079 Uiso 1 1 d D . .
C19 C 0.5596(2) 0.66827(16) 0.82027(8) 0.0236(4) Uani 1 1 d . . .
H19A H 0.5178 0.5928 0.8321 0.028 Uiso 1 1 calc R . .
H19B H 0.6801 0.6638 0.8170 0.028 Uiso 1 1 calc R . .
O20 O 0.51561(17) 0.74806(12) 0.86662(6) 0.0276(3) Uani 1 1 d . . .
C21 C 0.5917(3) 0.7227(2) 0.92570(9) 0.0302(4) Uani 1 1 d . . .
H21A H 0.5707 0.6429 0.9367 0.036 Uiso 1 1 calc R . .
H21B H 0.5431 0.7706 0.9588 0.036 Uiso 1 1 calc R . .
C22 C 0.7742(2) 0.74297(17) 0.92313(8) 0.0249(4) Uani 1 1 d . . .
C23 C 0.8339(3) 0.85296(19) 0.92483(10) 0.0323(5) Uani 1 1 d . . .
H23 H 0.7600 0.9139 0.9306 0.039 Uiso 1 1 calc R . .
C24 C 0.9993(3) 0.8749(2) 0.91827(11) 0.0398(5) Uani 1 1 d . . .
H24 H 1.0379 0.9505 0.9190 0.048 Uiso 1 1 calc R . .
C25 C 1.1083(3) 0.7867(2) 0.91068(10) 0.0383(5) Uani 1 1 d . . .
H25 H 1.2217 0.8018 0.9060 0.046 Uiso 1 1 calc R . .
C26 C 1.0521(3) 0.6768(2) 0.90991(10) 0.0353(5) Uani 1 1 d . . .
H26 H 1.1269 0.6161 0.9052 0.042 Uiso 1 1 calc R . .
C27 C 0.8845(3) 0.65496(18) 0.91603(9) 0.0298(4) Uani 1 1 d . . .
H27 H 0.8461 0.5793 0.9153 0.036 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
O1 0.0238(6) 0.0246(6) 0.0203(6) -0.0004(5) 0.0035(5) -0.0024(5)
C2 0.0284(10) 0.0347(11) 0.0226(9) 0.0021(8) 0.0024(8) -0.0009(8)
C3 0.0381(12) 0.0463(13) 0.0203(9) -0.0038(8) 0.0068(8) -0.0007(10)
C4 0.0369(11) 0.0361(11) 0.0233(10) -0.0094(8) 0.0010(8) 0.0064(9)
C5 0.0283(10) 0.0268(9) 0.0248(9) -0.0041(8) 0.0002(8) 0.0050(8)
C6 0.0232(8) 0.0224(8) 0.0177(8) -0.0014(7) -0.0003(6) 0.0010(7)
O7 0.0230(7) 0.0254(6) 0.0183(6) -0.0016(5) -0.0007(5) 0.0043(5)
C8 0.0194(8) 0.0212(8) 0.0178(8) -0.0011(6) -0.0006(6) 0.0002(7)
C9 0.0200(9) 0.0246(9) 0.0191(8) 0.0018(7) 0.0006(7) -0.0021(7)
C10 0.0174(8) 0.0197(8) 0.0214(8) 0.0006(6) -0.0002(6) -0.0017(6)
C11 0.0225(9) 0.0232(8) 0.0215(8) -0.0032(7) -0.0029(7) -0.0016(7)
S12 0.0181(2) 0.0280(2) 0.0341(3) -0.00259(19) -0.00328(18) -0.00485(17)
C13 0.0191(9) 0.0372(11) 0.0384(11) -0.0026(9) 0.0023(8) -0.0003(8)
C14 0.0250(10) 0.0304(10) 0.0485(13) -0.0024(9) 0.0009(9) 0.0065(8)
C15 0.0291(10) 0.0233(9) 0.0396(12) -0.0040(8) 0.0046(9) 0.0017(8)
S16 0.0233(2) 0.0211(2) 0.0280(2) 0.00277(17) 0.00286(17) -0.00092(17)
C17 0.0440(13) 0.0347(11) 0.0370(11) 0.0039(10) 0.0138(10) -0.0042(10)
O18 0.0747(15) 0.0395(10) 0.0834(16) 0.0052(10) 0.0314(13) -0.0047(10)
C19 0.0253(9) 0.0261(9) 0.0193(8) -0.0018(7) -0.0008(7) 0.0035(7)
O20 0.0241(7) 0.0386(8) 0.0202(6) -0.0065(6) -0.0020(5) 0.0063(6)
C21 0.0272(10) 0.0455(12) 0.0178(9) -0.0015(8) -0.0005(7) -0.0017(9)
C22 0.0266(9) 0.0314(9) 0.0168(8) 0.0014(7) -0.0012(7) 0.0000(8)
C23 0.0324(11) 0.0302(10) 0.0342(11) 0.0028(9) -0.0022(8) 0.0032(9)
C24 0.0407(13) 0.0400(12) 0.0386(12) 0.0022(10) -0.0019(10) -0.0102(10)
C25 0.0255(10) 0.0615(16) 0.0280(11) -0.0012(10) 0.0004(9) -0.0025(10)
C26 0.0330(11) 0.0499(13) 0.0229(9) -0.0055(9) -0.0029(8) 0.0145(10)
C27 0.0389(11) 0.0303(11) 0.0203(9) -0.0003(7) -0.0057(8) 0.0034(9)
_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
O1 C6 1.438(2) . ?
O1 C2 1.439(2) . ?
C2 C17 1.512(3) . ?
C2 C3 1.519(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.529(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.527(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.527(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O7 1.401(2) . ?
C6 C11 1.536(2) . ?
O7 C8 1.444(2) . ?
C8 C19 1.512(2) . ?
C8 C9 1.521(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.533(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.541(2) . ?
C10 S12 1.8277(18) . ?
C10 S16 1.8341(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
S12 C13 1.811(2) . ?
C13 C14 1.517(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 S16 1.816(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 O18 1.409(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
O18 H18 1.031(18) . ?
C19 O20 1.415(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
O20 C21 1.438(2) . ?
C21 C22 1.513(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.388(3) . ?
C22 C23 1.393(3) . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.402(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
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
C6 O1 C2 115.99(14) . . ?
O1 C2 C17 104.93(17) . . ?
O1 C2 C3 111.56(17) . . ?
C17 C2 C3 112.58(18) . . ?
O1 C2 H2 109.2 . . ?
C17 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C2 C3 C4 110.56(17) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 109.74(17) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C4 C5 C6 112.11(16) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O7 C6 O1 106.09(14) . . ?
O7 C6 C5 104.80(15) . . ?
O1 C6 C5 109.93(14) . . ?
O7 C6 C11 111.32(14) . . ?
O1 C6 C11 111.76(15) . . ?
C5 C6 C11 112.52(16) . . ?
C6 O7 C8 116.48(14) . . ?
O7 C8 C19 102.80(14) . . ?
O7 C8 C9 109.95(15) . . ?
C19 C8 C9 113.53(15) . . ?
O7 C8 H8 110.1 . . ?
C19 C8 H8 110.1 . . ?
C9 C8 H8 110.1 . . ?
C8 C9 C10 110.41(14) . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C11 108.68(14) . . ?
C9 C10 S12 112.02(12) . . ?
C11 C10 S12 104.23(11) . . ?
C9 C10 S16 111.87(12) . . ?
C11 C10 S16 109.85(12) . . ?
S12 C10 S16 109.90(9) . . ?
C6 C11 C10 115.30(15) . . ?
C6 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C6 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C13 S12 C10 101.78(9) . . ?
C14 C13 S12 114.06(15) . . ?
C14 C13 H13A 108.7 . . ?
S12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
S12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 114.11(18) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 S16 114.67(15) . . ?
C14 C15 H15A 108.6 . . ?
S16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
S16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C15 S16 C10 100.76(9) . . ?
O18 C17 C2 112.45(18) . . ?
O18 C17 H17A 109.1 . . ?
C2 C17 H17A 109.1 . . ?
O18 C17 H17B 109.1 . . ?
C2 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C17 O18 H18 106.2(19) . . ?
O20 C19 C8 109.51(14) . . ?
O20 C19 H19A 109.8 . . ?
C8 C19 H19A 109.8 . . ?
O20 C19 H19B 109.8 . . ?
C8 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C19 O20 C21 111.28(15) . . ?
O20 C21 C22 111.26(16) . . ?
O20 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
O20 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C27 C22 C23 118.6(2) . . ?
C27 C22 C21 121.8(2) . . ?
C23 C22 C21 119.57(19) . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C23 120.0(2) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 120.0(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C22 C27 C26 120.5(2) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
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
C6 O1 C2 C17 -178.26(16) . . . . ?
C6 O1 C2 C3 -56.1(2) . . . . ?
O1 C2 C3 C4 53.8(2) . . . . ?
C17 C2 C3 C4 171.45(19) . . . . ?
C2 C3 C4 C5 -53.5(2) . . . . ?
C3 C4 C5 C6 54.0(2) . . . . ?
C2 O1 C6 O7 167.71(15) . . . . ?
C2 O1 C6 C5 54.9(2) . . . . ?
C2 O1 C6 C11 -70.79(19) . . . . ?
C4 C5 C6 O7 -166.96(17) . . . . ?
C4 C5 C6 O1 -53.3(2) . . . . ?
C4 C5 C6 C11 71.9(2) . . . . ?
O1 C6 O7 C8 70.02(18) . . . . ?
C5 C6 O7 C8 -173.67(15) . . . . ?
C11 C6 O7 C8 -51.8(2) . . . . ?
C6 O7 C8 C19 -178.92(15) . . . . ?
C6 O7 C8 C9 59.9(2) . . . . ?
O7 C8 C9 C10 -59.14(19) . . . . ?
C19 C8 C9 C10 -173.67(14) . . . . ?
C8 C9 C10 C11 53.10(19) . . . . ?
C8 C9 C10 S12 167.72(12) . . . . ?
C8 C9 C10 S16 -68.36(17) . . . . ?
O7 C6 C11 C10 45.5(2) . . . . ?
O1 C6 C11 C10 -72.97(19) . . . . ?
C5 C6 C11 C10 162.77(15) . . . . ?
C9 C10 C11 C6 -47.0(2) . . . . ?
S12 C10 C11 C6 -166.61(14) . . . . ?
S16 C10 C11 C6 75.68(17) . . . . ?
C9 C10 S12 C13 65.27(14) . . . . ?
C11 C10 S12 C13 -177.41(13) . . . . ?
S16 C10 S12 C13 -59.74(12) . . . . ?
C10 S12 C13 C14 59.03(18) . . . . ?
S12 C13 C14 C15 -63.1(2) . . . . ?
C13 C14 C15 S16 63.8(2) . . . . ?
C14 C15 S16 C10 -59.61(17) . . . . ?
C9 C10 S16 C15 -65.60(14) . . . . ?
C11 C10 S16 C15 173.61(13) . . . . ?
S12 C10 S16 C15 59.49(11) . . . . ?
O1 C2 C17 O18 -55.9(3) . . . . ?
C3 C2 C17 O18 -177.4(2) . . . . ?
O7 C8 C19 O20 172.76(14) . . . . ?
C9 C8 C19 O20 -68.5(2) . . . . ?
C8 C19 O20 C21 -175.50(15) . . . . ?
C19 O20 C21 C22 69.7(2) . . . . ?
O20 C21 C22 C27 -101.1(2) . . . . ?
O20 C21 C22 C23 75.7(2) . . . . ?
C27 C22 C23 C24 1.4(3) . . . . ?
C21 C22 C23 C24 -175.56(19) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C24 C25 C26 C27 0.8(3) . . . . ?
C23 C22 C27 C26 -0.8(3) . . . . ?
C21 C22 C27 C26 176.04(18) . . . . ?
C25 C26 C27 C22 -0.3(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.986
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.051

# Attachment 'Crystallographic CIF of compound 2c.doc'

#Crystallographic CIF of compound 2c

data_sl0512
_database_code_depnum_ccdc_archive 'CCDC 600004'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H29 Br O4 S2'
_chemical_formula_sum            'C21 H29 Br O4 S2'
_chemical_formula_weight         489.47
_chemical_absolute_configuration 
'The absolute configuration was determined reliably'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   13.4354(4)
_cell_length_b                   16.5257(6)
_cell_length_c                   9.9835(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2216.63(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    16266
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.03
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    2.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.739
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_special_details           
;
The -OH hydrogen atom was located and its position was refined
satisfactorily. The absolute structure was determined (Flack
parameter 0.01(2)).
;
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

#Crystallographic CIF of compound 2c
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_reflns_number            13524
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.86
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3866
_reflns_number_gt                3486
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_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^)+(0.0741P)^2^+1.9578P] 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    mixed
_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   0.003(15)
_refine_ls_number_reflns         3866
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.001
_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
O1 O -0.0484(2) 0.20408(17) -0.5807(3) 0.0328(7) Uani 1 1 d . . .
C2 C -0.0339(3) 0.1928(3) -0.4387(5) 0.0374(10) Uani 1 1 d . . .
H2 H 0.0157 0.2330 -0.4047 0.045 Uiso 1 1 calc R . .
C3 C -0.1310(4) 0.2027(3) -0.3644(5) 0.0436(12) Uani 1 1 d . . .
H3A H -0.1189 0.1985 -0.2668 0.052 Uiso 1 1 calc R . .
H3B H -0.1772 0.1587 -0.3904 0.052 Uiso 1 1 calc R . .
C4 C -0.1783(4) 0.2843(3) -0.3960(5) 0.0438(12) Uani 1 1 d . . .
H4A H -0.1357 0.3286 -0.3617 0.053 Uiso 1 1 calc R . .
H4B H -0.2442 0.2884 -0.3521 0.053 Uiso 1 1 calc R . .
C5 C -0.1903(3) 0.2923(3) -0.5494(5) 0.0380(11) Uani 1 1 d . . .
H5A H -0.2384 0.2514 -0.5821 0.046 Uiso 1 1 calc R . .
H5B H -0.2166 0.3466 -0.5717 0.046 Uiso 1 1 calc R . .
C6 C -0.0902(3) 0.2799(3) -0.6179(5) 0.0315(10) Uani 1 1 d . . .
C7 C -0.0998(3) 0.2763(3) -0.7697(5) 0.0366(11) Uani 1 1 d . . .
H7A H -0.1435 0.3211 -0.7993 0.044 Uiso 1 1 calc R . .
H7B H -0.1329 0.2249 -0.7943 0.044 Uiso 1 1 calc R . .
C8 C -0.0009(3) 0.2821(3) -0.8459(5) 0.0355(10) Uani 1 1 d . . .
C9 C 0.0592(4) 0.3520(3) -0.7871(5) 0.0372(10) Uani 1 1 d . . .
H9A H 0.1266 0.3520 -0.8273 0.045 Uiso 1 1 calc R . .
H9B H 0.0266 0.4038 -0.8110 0.045 Uiso 1 1 calc R . .
C10 C 0.0684(3) 0.3466(3) -0.6365(5) 0.0325(10) Uani 1 1 d . . .
H10 H 0.1062 0.2968 -0.6108 0.039 Uiso 1 1 calc R . .
O11 O -0.0293(2) 0.34543(17) -0.5774(3) 0.0334(7) Uani 1 1 d . . .
C12 C 0.0082(4) 0.1080(3) -0.4263(5) 0.0427(11) Uani 1 1 d . . .
H12A H 0.0213 0.0962 -0.3308 0.051 Uiso 1 1 calc R . .
H12B H -0.0417 0.0687 -0.4589 0.051 Uiso 1 1 calc R . .
O13 O 0.0981(3) 0.0982(2) -0.5006(4) 0.0524(10) Uani 1 1 d D . .
H13 H 0.093(5) 0.135(3) -0.579(4) 0.063 Uiso 1 1 d D . .
S14 S -0.03836(9) 0.30184(9) -1.01921(14) 0.0470(3) Uani 1 1 d . . .
C15 C 0.0788(4) 0.2975(4) -1.1086(6) 0.0553(14) Uani 1 1 d . . .
H15A H 0.0670 0.3092 -1.2045 0.066 Uiso 1 1 calc R . .
H15B H 0.1242 0.3395 -1.0729 0.066 Uiso 1 1 calc R . .
C16 C 0.1276(4) 0.2153(4) -1.0951(7) 0.0595(16) Uani 1 1 d . . .
H16A H 0.0789 0.1729 -1.1197 0.071 Uiso 1 1 calc R . .
H16B H 0.1841 0.2118 -1.1585 0.071 Uiso 1 1 calc R . .
C17 C 0.1649(4) 0.1996(4) -0.9553(6) 0.0518(14) Uani 1 1 d . . .
H17A H 0.2067 0.2458 -0.9267 0.062 Uiso 1 1 calc R . .
H17B H 0.2074 0.1507 -0.9563 0.062 Uiso 1 1 calc R . .
S18 S 0.06526(8) 0.18522(7) -0.83270(14) 0.0391(3) Uani 1 1 d . . .
C19 C 0.1203(3) 0.4210(3) -0.5838(6) 0.0400(11) Uani 1 1 d . . .
H19A H 0.1821 0.4302 -0.6355 0.048 Uiso 1 1 calc R . .
H19B H 0.0766 0.4686 -0.5964 0.048 Uiso 1 1 calc R . .
O20 O 0.1441(3) 0.41301(19) -0.4461(4) 0.0415(8) Uani 1 1 d . . .
C21 C 0.1872(6) 0.4871(4) -0.4023(7) 0.0707(19) Uani 1 1 d . . .
H21A H 0.1382 0.5314 -0.4125 0.085 Uiso 1 1 calc R . .
H21B H 0.2457 0.5000 -0.4587 0.085 Uiso 1 1 calc R . .
C22 C 0.2184(5) 0.4814(3) -0.2599(6) 0.0522(14) Uani 1 1 d . . .
C23 C 0.3099(6) 0.4506(4) -0.2239(8) 0.0693(19) Uani 1 1 d . . .
H23 H 0.3517 0.4286 -0.2915 0.083 Uiso 1 1 calc R . .
C24 C 0.3424(5) 0.4506(4) -0.0943(8) 0.0655(17) Uani 1 1 d . . .
H24 H 0.4063 0.4296 -0.0725 0.079 Uiso 1 1 calc R . .
C25 C 0.2818(4) 0.4813(3) 0.0040(6) 0.0515(13) Uani 1 1 d . . .
C26 C 0.1881(4) 0.5091(3) -0.0258(6) 0.0508(13) Uani 1 1 d . . .
H26 H 0.1451 0.5278 0.0432 0.061 Uiso 1 1 calc R . .
C27 C 0.1573(4) 0.5093(3) -0.1583(6) 0.0540(14) Uani 1 1 d . . .
H27 H 0.0929 0.5291 -0.1799 0.065 Uiso 1 1 calc R . .
Br28 Br 0.33053(7) 0.49177(6) 0.17770(8) 0.0913(3) Uani 1 1 d . . .
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
O1 0.0262(15) 0.0270(15) 0.0453(18) -0.0023(13) -0.0033(13) -0.0007(13)
C2 0.031(2) 0.037(2) 0.044(3) -0.002(2) -0.0072(18) -0.005(2)
C3 0.039(3) 0.040(3) 0.052(3) 0.004(2) 0.002(2) -0.007(2)
C4 0.032(2) 0.045(3) 0.055(3) -0.004(2) 0.008(2) -0.006(2)
C5 0.019(2) 0.044(3) 0.051(3) -0.007(2) 0.0063(18) 0.000(2)
C6 0.024(2) 0.028(2) 0.042(3) -0.0031(17) -0.0003(18) -0.0003(17)
C7 0.021(2) 0.043(3) 0.046(3) -0.001(2) -0.0013(19) 0.0028(19)
C8 0.0223(19) 0.035(2) 0.049(3) 0.001(2) 0.002(2) 0.0042(17)
C9 0.030(2) 0.034(2) 0.048(3) -0.003(2) 0.004(2) 0.0020(19)
C10 0.019(2) 0.027(2) 0.051(3) 0.0007(18) 0.0042(18) 0.0010(17)
O11 0.0245(15) 0.0277(15) 0.0478(18) -0.0020(13) 0.0042(12) -0.0006(12)
C12 0.037(3) 0.042(3) 0.049(3) 0.004(2) -0.011(2) 0.000(2)
O13 0.0355(19) 0.048(2) 0.074(3) 0.0048(19) -0.0071(19) 0.0083(16)
S14 0.0412(7) 0.0555(8) 0.0442(7) 0.0000(6) -0.0008(5) 0.0073(6)
C15 0.050(3) 0.067(4) 0.049(3) -0.006(3) 0.009(2) -0.011(3)
C16 0.040(3) 0.075(4) 0.064(4) -0.021(3) 0.021(3) -0.006(3)
C17 0.027(2) 0.055(3) 0.074(4) -0.016(3) 0.008(2) 0.004(2)
S18 0.0240(5) 0.0360(6) 0.0574(7) -0.0062(5) -0.0019(5) 0.0045(4)
C19 0.025(2) 0.031(2) 0.064(3) 0.003(2) 0.004(2) 0.0015(19)
O20 0.0376(19) 0.0307(17) 0.056(2) -0.0015(15) -0.0030(15) -0.0068(14)
C21 0.106(5) 0.033(3) 0.073(4) -0.005(3) -0.010(4) -0.027(3)
C22 0.063(4) 0.033(3) 0.060(3) -0.006(2) -0.004(3) -0.013(3)
C23 0.069(4) 0.052(3) 0.087(5) -0.018(3) 0.019(4) 0.011(3)
C24 0.046(3) 0.061(4) 0.090(5) 0.000(3) -0.002(3) 0.017(3)
C25 0.048(3) 0.037(3) 0.068(4) -0.007(3) -0.005(3) -0.004(2)
C26 0.037(3) 0.042(3) 0.073(4) -0.007(3) 0.007(3) -0.002(2)
C27 0.036(3) 0.042(3) 0.085(4) -0.002(3) -0.012(3) -0.007(2)
Br28 0.1040(6) 0.0970(6) 0.0729(5) 0.0282(4) -0.0313(4) -0.0383(5)
_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
O1 C6 1.422(5) . ?
O1 C2 1.444(6) . ?
C2 C3 1.510(7) . ?
C2 C12 1.516(7) . ?
C2 H2 1.0000 . ?
C3 C4 1.525(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.545(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.522(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O11 1.417(5) . ?
C6 C7 1.521(7) . ?
C7 C8 1.534(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.528(7) . ?
C8 S14 1.831(5) . ?
C8 S18 1.836(4) . ?
C9 C10 1.511(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O11 1.440(5) . ?
C10 C19 1.508(6) . ?
C10 H10 1.0000 . ?
C12 O13 1.426(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O13 H13 0.99(2) . ?
S14 C15 1.811(6) . ?
C15 C16 1.514(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.506(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 S18 1.829(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 O20 1.417(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
O20 C21 1.423(6) . ?
C21 C22 1.485(9) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.377(10) . ?
C22 C27 1.385(9) . ?
C23 C24 1.366(11) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.373(8) . ?
C25 Br28 1.862(6) . ?
C26 C27 1.386(9) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
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
C6 O1 C2 115.0(3) . . ?
O1 C2 C3 110.6(4) . . ?
O1 C2 C12 104.4(4) . . ?
C3 C2 C12 112.5(4) . . ?
O1 C2 H2 109.7 . . ?
C3 C2 H2 109.7 . . ?
C12 C2 H2 109.7 . . ?
C2 C3 C4 110.7(4) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C3 C4 C5 108.9(4) . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C6 C5 C4 110.0(4) . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
O11 C6 O1 111.8(3) . . ?
O11 C6 C7 111.2(4) . . ?
O1 C6 C7 105.0(4) . . ?
O11 C6 C5 106.2(4) . . ?
O1 C6 C5 110.5(4) . . ?
C7 C6 C5 112.2(4) . . ?
C6 C7 C8 114.8(4) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 108.3(4) . . ?
C9 C8 S14 111.9(3) . . ?
C7 C8 S14 104.0(3) . . ?
C9 C8 S18 112.1(3) . . ?
C7 C8 S18 109.2(3) . . ?
S14 C8 S18 110.9(2) . . ?
C10 C9 C8 112.4(4) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
O11 C10 C19 106.8(4) . . ?
O11 C10 C9 109.5(4) . . ?
C19 C10 C9 109.7(4) . . ?
O11 C10 H10 110.3 . . ?
C19 C10 H10 110.3 . . ?
C9 C10 H10 110.3 . . ?
C6 O11 C10 114.9(3) . . ?
O13 C12 C2 112.2(4) . . ?
O13 C12 H12A 109.2 . . ?
C2 C12 H12A 109.2 . . ?
O13 C12 H12B 109.2 . . ?
C2 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 O13 H13 107(4) . . ?
C15 S14 C8 102.7(3) . . ?
C16 C15 S14 111.6(4) . . ?
C16 C15 H15A 109.3 . . ?
S14 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
S14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 112.4(5) . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 S18 113.5(4) . . ?
C16 C17 H17A 108.9 . . ?
S18 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
S18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 S18 C8 101.1(2) . . ?
O20 C19 C10 111.6(4) . . ?
O20 C19 H19A 109.3 . . ?
C10 C19 H19A 109.3 . . ?
O20 C19 H19B 109.3 . . ?
C10 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C19 O20 C21 108.1(4) . . ?
O20 C21 C22 110.7(5) . . ?
O20 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
O20 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C23 C22 C27 117.5(6) . . ?
C23 C22 C21 121.7(6) . . ?
C27 C22 C21 120.8(6) . . ?
C24 C23 C22 122.2(6) . . ?
C24 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?
C23 C24 C25 119.2(6) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C26 120.9(6) . . ?
C24 C25 Br28 119.4(5) . . ?
C26 C25 Br28 119.5(5) . . ?
C25 C26 C27 118.7(5) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C22 C27 C26 121.4(5) . . ?
C22 C27 H27 119.3 . . ?
C26 C27 H27 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
C6 O1 C2 C3 57.4(5) . . . . ?
C6 O1 C2 C12 178.6(3) . . . . ?
O1 C2 C3 C4 -55.3(5) . . . . ?
C12 C2 C3 C4 -171.6(4) . . . . ?
C2 C3 C4 C5 55.4(5) . . . . ?
C3 C4 C5 C6 -55.4(5) . . . . ?
C2 O1 C6 O11 60.3(5) . . . . ?
C2 O1 C6 C7 -179.0(3) . . . . ?
C2 O1 C6 C5 -57.8(5) . . . . ?
C4 C5 C6 O11 -65.6(5) . . . . ?
C4 C5 C6 O1 55.8(5) . . . . ?
C4 C5 C6 C7 172.7(4) . . . . ?
O11 C6 C7 C8 48.8(5) . . . . ?
O1 C6 C7 C8 -72.3(5) . . . . ?
C5 C6 C7 C8 167.6(4) . . . . ?
C6 C7 C8 C9 -47.0(5) . . . . ?
C6 C7 C8 S14 -166.2(3) . . . . ?
C6 C7 C8 S18 75.3(4) . . . . ?
C7 C8 C9 C10 51.6(5) . . . . ?
S14 C8 C9 C10 165.7(3) . . . . ?
S18 C8 C9 C10 -69.0(4) . . . . ?
C8 C9 C10 O11 -58.0(5) . . . . ?
C8 C9 C10 C19 -174.9(4) . . . . ?
O1 C6 O11 C10 61.9(5) . . . . ?
C7 C6 O11 C10 -55.2(5) . . . . ?
C5 C6 O11 C10 -177.5(4) . . . . ?
C19 C10 O11 C6 178.8(4) . . . . ?
C9 C10 O11 C6 60.1(5) . . . . ?
O1 C2 C12 O13 57.9(5) . . . . ?
C3 C2 C12 O13 177.9(4) . . . . ?
C9 C8 S14 C15 69.1(4) . . . . ?
C7 C8 S14 C15 -174.2(3) . . . . ?
S18 C8 S14 C15 -56.8(3) . . . . ?
C8 S14 C15 C16 60.7(5) . . . . ?
S14 C15 C16 C17 -69.5(6) . . . . ?
C15 C16 C17 S18 69.8(6) . . . . ?
C16 C17 S18 C8 -59.6(5) . . . . ?
C9 C8 S18 C17 -70.7(4) . . . . ?
C7 C8 S18 C17 169.3(3) . . . . ?
S14 C8 S18 C17 55.2(3) . . . . ?
O11 C10 C19 O20 70.4(4) . . . . ?
C9 C10 C19 O20 -171.1(4) . . . . ?
C10 C19 O20 C21 -176.6(5) . . . . ?
C19 O20 C21 C22 -177.3(5) . . . . ?
O20 C21 C22 C23 85.6(8) . . . . ?
O20 C21 C22 C27 -96.4(7) . . . . ?
C27 C22 C23 C24 -3.1(9) . . . . ?
C21 C22 C23 C24 175.0(6) . . . . ?
C22 C23 C24 C25 0.9(10) . . . . ?
C23 C24 C25 C26 2.3(10) . . . . ?
C23 C24 C25 Br28 -173.5(5) . . . . ?
C24 C25 C26 C27 -3.1(8) . . . . ?
Br28 C25 C26 C27 172.7(4) . . . . ?
C23 C22 C27 C26 2.2(8) . . . . ?
C21 C22 C27 C26 -175.8(5) . . . . ?
C25 C26 C27 C22 0.8(8) . . . . ?
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.082