# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Darren Dixon'
'Caroline L Rigby'

_publ_contact_author_name        'Darren Dixon'
_publ_contact_author_email       DARREN.DIXON@MAN.AC.UK

_publ_section_title              
;
Enantioselective Organocatalytic Michael Additions to
Acrylic Acid Derivatives: Generation of All-Carbon Quaternary
Stereocentres
;

# Attachment 's2637m.cif'

data_s2637m
_database_code_depnum_ccdc_archive 'CCDC 683070'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 Br O4 S'
_chemical_formula_weight         525.44

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(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                   10.343(5)
_cell_length_b                   12.962(5)
_cell_length_c                   18.230(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2444.0(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    759
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      19.33

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    1.798
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12364
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_av_sigmaI/netI    0.1323
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4305
_reflns_number_gt                2583
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.0115P)^2^+0.0000P] 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'
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   -0.008(10)
_refine_ls_number_reflns         4305
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0670
_refine_ls_goodness_of_fit_ref   0.771
_refine_ls_restrained_S_all      0.771
_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
Br1 Br 0.86214(6) 0.26176(4) 0.13642(3) 0.05389(19) Uani 1 1 d . . .
S1 S 0.71803(14) 0.47278(8) 0.63773(9) 0.0445(4) Uani 1 1 d . . .
O1 O 0.5178(3) 0.1618(2) 0.45650(19) 0.0360(9) Uani 1 1 d . . .
O2 O 0.7018(4) 0.2812(2) 0.68463(18) 0.0494(11) Uani 1 1 d . . .
O3 O 0.7279(3) -0.0280(2) 0.41666(17) 0.0321(9) Uani 1 1 d . . .
O4 O 0.7379(3) -0.0296(2) 0.54032(18) 0.0386(9) Uani 1 1 d . . .
C1 C 0.7476(4) 0.1322(3) 0.4758(2) 0.0232(12) Uani 1 1 d . . .
C2 C 0.6268(5) 0.1665(3) 0.4326(3) 0.0242(12) Uani 1 1 d . . .
C3 C 0.6680(4) 0.2014(3) 0.3596(3) 0.0220(11) Uani 1 1 d . . .
C4 C 0.5929(5) 0.2297(4) 0.3006(3) 0.0325(13) Uani 1 1 d . . .
H4 H 0.5036 0.2348 0.3054 0.039 Uiso 1 1 calc R . .
C5 C 0.6518(5) 0.2506(3) 0.2342(2) 0.0369(13) Uani 1 1 d . . .
H5 H 0.6027 0.2690 0.1935 0.044 Uiso 1 1 calc R . .
C6 C 0.7863(5) 0.2436(4) 0.2293(2) 0.0287(12) Uani 1 1 d . . .
C7 C 0.8606(5) 0.2181(3) 0.2884(3) 0.0274(12) Uani 1 1 d . . .
H7 H 0.9502 0.2157 0.2842 0.033 Uiso 1 1 calc R . .
C8 C 0.8023(4) 0.1958(3) 0.3542(3) 0.0184(11) Uani 1 1 d . . .
C9 C 0.8603(5) 0.1643(3) 0.4259(2) 0.0241(12) Uani 1 1 d . . .
H9A H 0.9076 0.2213 0.4475 0.029 Uiso 1 1 calc R . .
H9B H 0.9194 0.1070 0.4190 0.029 Uiso 1 1 calc R . .
C10 C 0.7472(5) 0.1804(3) 0.5524(2) 0.0268(13) Uani 1 1 d . . .
H10A H 0.6794 0.1481 0.5811 0.032 Uiso 1 1 calc R . .
H10B H 0.8289 0.1647 0.5760 0.032 Uiso 1 1 calc R . .
C11 C 0.7269(5) 0.2970(3) 0.5541(2) 0.0210(12) Uani 1 1 d . . .
H11A H 0.7987 0.3308 0.5297 0.025 Uiso 1 1 calc R . .
H11B H 0.6483 0.3142 0.5278 0.025 Uiso 1 1 calc R . .
C12 C 0.7173(4) 0.3350(3) 0.6311(3) 0.0270(12) Uani 1 1 d . . .
C13 C 0.6694(5) 0.4894(3) 0.7323(3) 0.0346(14) Uani 1 1 d . . .
C14 C 0.5408(5) 0.5049(4) 0.7460(3) 0.0416(16) Uani 1 1 d . . .
H14 H 0.4828 0.5087 0.7071 0.050 Uiso 1 1 calc R . .
C15 C 0.4964(5) 0.5152(4) 0.8178(3) 0.0407(16) Uani 1 1 d . . .
H15 H 0.4086 0.5253 0.8262 0.049 Uiso 1 1 calc R . .
C16 C 0.5787(6) 0.5109(3) 0.8759(3) 0.0423(17) Uani 1 1 d . . .
H16 H 0.5479 0.5167 0.9237 0.051 Uiso 1 1 calc R . .
C17 C 0.7153(6) 0.4970(3) 0.8617(4) 0.0435(15) Uani 1 1 d . . .
C18 C 0.7997(8) 0.4912(5) 0.9206(4) 0.064(2) Uani 1 1 d . . .
H18 H 0.7689 0.4949 0.9685 0.076 Uiso 1 1 calc R . .
C19 C 0.9317(8) 0.4796(5) 0.9070(5) 0.078(3) Uani 1 1 d . . .
H19 H 0.9897 0.4777 0.9460 0.094 Uiso 1 1 calc R . .
C20 C 0.9770(7) 0.4709(5) 0.8351(5) 0.069(3) Uani 1 1 d . . .
H20 H 1.0653 0.4631 0.8272 0.083 Uiso 1 1 calc R . .
C21 C 0.8959(6) 0.4734(4) 0.7761(4) 0.061(2) Uani 1 1 d . . .
H21 H 0.9282 0.4666 0.7288 0.073 Uiso 1 1 calc R . .
C22 C 0.7595(6) 0.4868(3) 0.7883(3) 0.0312(14) Uani 1 1 d . . .
C23 C 0.7385(5) 0.0155(4) 0.4836(3) 0.0264(12) Uani 1 1 d . . .
C24 C 0.7029(5) -0.1404(4) 0.4089(3) 0.0332(14) Uani 1 1 d . . .
C25 C 0.5704(5) -0.1653(3) 0.4416(3) 0.0386(15) Uani 1 1 d . . .
H25A H 0.5705 -0.1492 0.4930 0.058 Uiso 1 1 calc R . .
H25B H 0.5520 -0.2373 0.4350 0.058 Uiso 1 1 calc R . .
H25C H 0.5054 -0.1249 0.4173 0.058 Uiso 1 1 calc R . .
C26 C 0.8090(5) -0.2015(4) 0.4459(3) 0.0570(19) Uani 1 1 d . . .
H26A H 0.8916 -0.1779 0.4287 0.086 Uiso 1 1 calc R . .
H26B H 0.7991 -0.2734 0.4344 0.086 Uiso 1 1 calc R . .
H26C H 0.8037 -0.1921 0.4981 0.086 Uiso 1 1 calc R . .
C27 C 0.7032(5) -0.1558(4) 0.3269(3) 0.0466(17) Uani 1 1 d . . .
H27A H 0.6376 -0.1133 0.3051 0.070 Uiso 1 1 calc R . .
H27B H 0.6858 -0.2270 0.3160 0.070 Uiso 1 1 calc R . .
H27C H 0.7862 -0.1371 0.3075 0.070 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
Br1 0.0974(5) 0.0317(3) 0.0325(3) 0.0017(3) 0.0195(4) -0.0018(4)
S1 0.0778(11) 0.0224(7) 0.0332(8) -0.0045(7) 0.0057(10) -0.0047(7)
O1 0.020(2) 0.048(2) 0.041(2) -0.0108(18) 0.0013(19) 0.0002(18)
O2 0.097(3) 0.023(2) 0.029(2) 0.0019(17) 0.001(2) 0.002(2)
O3 0.038(2) 0.024(2) 0.034(2) -0.0099(15) 0.004(2) -0.0023(18)
O4 0.060(3) 0.0269(19) 0.028(2) 0.0017(17) -0.002(2) 0.0003(19)
C1 0.020(3) 0.023(3) 0.027(3) 0.003(2) 0.002(3) 0.002(2)
C2 0.022(3) 0.018(3) 0.032(3) -0.011(2) 0.003(3) -0.002(3)
C3 0.027(3) 0.016(2) 0.022(3) -0.004(2) -0.005(3) 0.003(2)
C4 0.023(3) 0.029(3) 0.045(4) -0.003(3) -0.007(3) 0.001(3)
C5 0.057(4) 0.022(3) 0.032(3) -0.003(3) -0.015(3) 0.002(3)
C6 0.051(4) 0.018(3) 0.017(3) 0.000(2) 0.006(3) -0.003(3)
C7 0.029(3) 0.018(3) 0.035(3) -0.004(2) 0.010(3) 0.000(3)
C8 0.020(3) 0.015(2) 0.020(3) -0.004(2) 0.002(3) -0.004(2)
C9 0.019(3) 0.022(3) 0.031(3) -0.007(2) 0.003(3) -0.004(3)
C10 0.025(3) 0.025(3) 0.031(3) -0.001(2) 0.007(3) -0.003(2)
C11 0.017(3) 0.021(3) 0.025(3) 0.002(2) -0.001(3) 0.000(2)
C12 0.031(3) 0.020(3) 0.030(3) -0.006(2) -0.004(3) 0.000(2)
C13 0.050(4) 0.022(3) 0.032(3) -0.002(2) 0.004(3) -0.005(3)
C14 0.052(5) 0.021(3) 0.051(4) -0.008(3) 0.009(4) -0.003(3)
C15 0.043(4) 0.034(3) 0.046(4) -0.013(3) 0.017(3) -0.007(3)
C16 0.066(5) 0.021(3) 0.041(4) -0.005(3) 0.014(4) -0.003(3)
C17 0.073(5) 0.015(3) 0.043(4) -0.007(3) -0.027(5) 0.008(3)
C18 0.118(7) 0.025(4) 0.047(5) -0.006(3) -0.017(5) -0.004(4)
C19 0.076(7) 0.037(4) 0.122(8) -0.025(5) -0.052(7) 0.000(5)
C20 0.057(5) 0.033(4) 0.116(8) -0.030(4) -0.033(5) 0.008(4)
C21 0.051(5) 0.021(3) 0.111(6) -0.020(3) -0.004(5) 0.001(3)
C22 0.054(4) 0.013(3) 0.026(3) -0.002(2) -0.002(3) -0.005(3)
C23 0.024(3) 0.028(3) 0.027(3) -0.004(3) -0.001(3) 0.002(3)
C24 0.039(4) 0.018(3) 0.043(4) -0.010(2) 0.004(3) -0.007(3)
C25 0.041(4) 0.026(3) 0.049(4) -0.005(3) 0.001(3) -0.003(3)
C26 0.039(4) 0.036(3) 0.096(6) -0.016(3) 0.002(4) 0.008(3)
C27 0.055(4) 0.042(4) 0.043(4) -0.024(3) 0.018(3) -0.019(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
Br1 C6 1.880(4) . ?
S1 C12 1.790(4) . ?
S1 C13 1.810(5) . ?
O1 C2 1.210(5) . ?
O2 C12 1.211(5) . ?
O3 C23 1.349(5) . ?
O3 C24 1.486(5) . ?
O4 C23 1.188(5) . ?
C1 C23 1.522(6) . ?
C1 C10 1.530(6) . ?
C1 C9 1.535(6) . ?
C1 C2 1.542(6) . ?
C2 C3 1.467(6) . ?
C3 C4 1.377(6) . ?
C3 C8 1.394(5) . ?
C4 C5 1.381(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.365(6) . ?
C7 C8 1.373(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.496(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.526(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.492(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 C14 1.368(6) . ?
C13 C22 1.382(7) . ?
C14 C15 1.395(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.360(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.448(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(7) . ?
C17 C22 1.421(8) . ?
C18 C19 1.396(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.397(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.364(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.438(7) . ?
C21 H21 0.9300 . ?
C24 C27 1.508(6) . ?
C24 C26 1.512(6) . ?
C24 C25 1.529(6) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C12 S1 C13 100.5(2) . . ?
C23 O3 C24 120.6(4) . . ?
C23 C1 C10 108.6(4) . . ?
C23 C1 C9 111.8(4) . . ?
C10 C1 C9 115.6(4) . . ?
C23 C1 C2 106.5(4) . . ?
C10 C1 C2 110.3(4) . . ?
C9 C1 C2 103.6(4) . . ?
O1 C2 C3 127.7(5) . . ?
O1 C2 C1 123.8(4) . . ?
C3 C2 C1 108.4(4) . . ?
C4 C3 C8 121.3(5) . . ?
C4 C3 C2 128.8(4) . . ?
C8 C3 C2 109.7(5) . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 118.9(4) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 121.7(4) . . ?
C7 C6 Br1 120.4(4) . . ?
C5 C6 Br1 117.8(4) . . ?
C6 C7 C8 119.6(5) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C3 119.3(5) . . ?
C7 C8 C9 130.1(4) . . ?
C3 C8 C9 110.6(5) . . ?
C8 C9 C1 106.7(4) . . ?
C8 C9 H9A 110.4 . . ?
C1 C9 H9A 110.4 . . ?
C8 C9 H9B 110.4 . . ?
C1 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C11 C10 C1 115.0(4) . . ?
C11 C10 H10A 108.5 . . ?
C1 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C1 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C10 110.8(4) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O2 C12 C11 125.3(4) . . ?
O2 C12 S1 121.4(4) . . ?
C11 C12 S1 113.2(3) . . ?
C14 C13 C22 121.7(5) . . ?
C14 C13 S1 117.4(4) . . ?
C22 C13 S1 120.9(4) . . ?
C13 C14 C15 120.3(6) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 121.4(5) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 118.5(6) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C18 C17 C22 121.5(6) . . ?
C18 C17 C16 118.9(7) . . ?
C22 C17 C16 119.6(6) . . ?
C17 C18 C19 119.0(7) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C20 C19 C18 120.2(8) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 122.1(8) . . ?
C21 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
C20 C21 C22 119.0(7) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C13 C22 C17 118.4(6) . . ?
C13 C22 C21 123.4(6) . . ?
C17 C22 C21 118.2(6) . . ?
O4 C23 O3 125.5(4) . . ?
O4 C23 C1 124.9(4) . . ?
O3 C23 C1 109.6(4) . . ?
O3 C24 C27 102.9(4) . . ?
O3 C24 C26 110.2(4) . . ?
C27 C24 C26 111.8(5) . . ?
O3 C24 C25 109.0(4) . . ?
C27 C24 C25 111.1(5) . . ?
C26 C24 C25 111.5(4) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C23 C1 C2 O1 67.9(5) . . . . ?
C10 C1 C2 O1 -49.8(6) . . . . ?
C9 C1 C2 O1 -174.1(4) . . . . ?
C23 C1 C2 C3 -110.5(4) . . . . ?
C10 C1 C2 C3 131.8(4) . . . . ?
C9 C1 C2 C3 7.5(4) . . . . ?
O1 C2 C3 C4 -4.8(8) . . . . ?
C1 C2 C3 C4 173.5(4) . . . . ?
O1 C2 C3 C8 179.4(4) . . . . ?
C1 C2 C3 C8 -2.2(5) . . . . ?
C8 C3 C4 C5 1.6(7) . . . . ?
C2 C3 C4 C5 -173.7(4) . . . . ?
C3 C4 C5 C6 -0.9(7) . . . . ?
C4 C5 C6 C7 -0.8(8) . . . . ?
C4 C5 C6 Br1 175.1(3) . . . . ?
C5 C6 C7 C8 1.7(7) . . . . ?
Br1 C6 C7 C8 -174.0(3) . . . . ?
C6 C7 C8 C3 -1.0(6) . . . . ?
C6 C7 C8 C9 178.8(4) . . . . ?
C4 C3 C8 C7 -0.7(6) . . . . ?
C2 C3 C8 C7 175.4(3) . . . . ?
C4 C3 C8 C9 179.5(4) . . . . ?
C2 C3 C8 C9 -4.4(5) . . . . ?
C7 C8 C9 C1 -170.6(4) . . . . ?
C3 C8 C9 C1 9.2(5) . . . . ?
C23 C1 C9 C8 104.5(4) . . . . ?
C10 C1 C9 C8 -130.5(4) . . . . ?
C2 C1 C9 C8 -9.8(4) . . . . ?
C23 C1 C10 C11 -167.6(4) . . . . ?
C9 C1 C10 C11 65.9(6) . . . . ?
C2 C1 C10 C11 -51.2(6) . . . . ?
C1 C10 C11 C12 175.4(4) . . . . ?
C10 C11 C12 O2 -13.7(7) . . . . ?
C10 C11 C12 S1 171.1(3) . . . . ?
C13 S1 C12 O2 -7.6(5) . . . . ?
C13 S1 C12 C11 167.8(4) . . . . ?
C12 S1 C13 C14 -94.7(4) . . . . ?
C12 S1 C13 C22 85.6(4) . . . . ?
C22 C13 C14 C15 -2.2(7) . . . . ?
S1 C13 C14 C15 178.1(4) . . . . ?
C13 C14 C15 C16 0.5(7) . . . . ?
C14 C15 C16 C17 1.1(7) . . . . ?
C15 C16 C17 C18 -179.2(5) . . . . ?
C15 C16 C17 C22 -0.9(7) . . . . ?
C22 C17 C18 C19 2.9(8) . . . . ?
C16 C17 C18 C19 -178.9(6) . . . . ?
C17 C18 C19 C20 -1.9(11) . . . . ?
C18 C19 C20 C21 0.1(12) . . . . ?
C19 C20 C21 C22 0.8(10) . . . . ?
C14 C13 C22 C17 2.3(7) . . . . ?
S1 C13 C22 C17 -178.1(3) . . . . ?
C14 C13 C22 C21 -178.2(5) . . . . ?
S1 C13 C22 C21 1.4(7) . . . . ?
C18 C17 C22 C13 177.5(5) . . . . ?
C16 C17 C22 C13 -0.7(7) . . . . ?
C18 C17 C22 C21 -2.0(7) . . . . ?
C16 C17 C22 C21 179.8(4) . . . . ?
C20 C21 C22 C13 -179.4(5) . . . . ?
C20 C21 C22 C17 0.1(8) . . . . ?
C24 O3 C23 O4 5.1(8) . . . . ?
C24 O3 C23 C1 -173.2(4) . . . . ?
C10 C1 C23 O4 -3.5(7) . . . . ?
C9 C1 C23 O4 125.3(5) . . . . ?
C2 C1 C23 O4 -122.2(6) . . . . ?
C10 C1 C23 O3 174.9(4) . . . . ?
C9 C1 C23 O3 -56.3(5) . . . . ?
C2 C1 C23 O3 56.2(5) . . . . ?
C23 O3 C24 C27 -178.0(5) . . . . ?
C23 O3 C24 C26 -58.7(6) . . . . ?
C23 O3 C24 C25 64.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.060