# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?

_publ_contact_author_email       xiaohuaxu@nankai.edu.cn
_publ_contact_author_name        'Prof. Xiaohua Xu'

_publ_section_title              
;
Zinc and indium-mediated Barbier-type allylation
of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous media:
an efficient synthesis method for a-methylene-g-butyrolactone
;
_publ_author_name                'Xiaohua Xu'

# Attachment '- r90519c-cif-for-8.cif'

data_r90519c
_database_code_depnum_ccdc_archive 'CCDC 869715'
#TrackingRef '- r90519c-cif-for-8.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H26 O3 S'
_chemical_formula_weight         358.48

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

_cell_length_a                   9.1092(18)
_cell_length_b                   10.189(2)
_cell_length_c                   20.517(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1904.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4883
_cell_measurement_theta_min      2.232
_cell_measurement_theta_max      27.857

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9637
_exptl_absorpt_correction_T_max  0.9744
_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            12100
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0481
_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       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3321
_reflns_number_gt                3001
_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^)+(0.0740P)^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     SHELXL
_refine_ls_extinction_coef       0.037(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   0.13(9)
_refine_ls_number_reflns         3321
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.002
_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 0.82808(8) 0.94476(7) 1.01138(4) 0.0359(2) Uani 1 1 d . . .
O1 O 0.7242(2) 0.63596(17) 0.97677(9) 0.0312(5) Uani 1 1 d . . .
O2 O 0.64325(19) 0.69008(16) 0.87888(7) 0.0240(4) Uani 1 1 d . . .
O3 O 0.2885(2) 0.9332(2) 0.89501(8) 0.0352(5) Uani 1 1 d . . .
H3 H 0.2632 0.9217 0.9329 0.053 Uiso 1 1 calc R . .
C1 C 0.8201(3) 1.1002(2) 0.97459(12) 0.0258(6) Uani 1 1 d . . .
C2 C 0.9123(3) 1.1274(3) 0.92236(14) 0.0352(7) Uani 1 1 d . . .
H2 H 0.9732 1.0619 0.9061 0.042 Uiso 1 1 calc R . .
C3 C 0.9146(3) 1.2503(3) 0.89441(13) 0.0369(7) Uani 1 1 d . . .
H3A H 0.9762 1.2669 0.8592 0.044 Uiso 1 1 calc R . .
C4 C 0.8268(3) 1.3480(3) 0.91810(13) 0.0323(6) Uani 1 1 d . . .
H4 H 0.8302 1.4312 0.8995 0.039 Uiso 1 1 calc R . .
C5 C 0.7335(3) 1.3236(3) 0.96929(13) 0.0330(7) Uani 1 1 d . . .
H5 H 0.6719 1.3896 0.9845 0.040 Uiso 1 1 calc R . .
C6 C 0.7310(3) 1.2005(3) 0.99829(13) 0.0295(6) Uani 1 1 d . . .
H6 H 0.6696 1.1850 1.0337 0.035 Uiso 1 1 calc R . .
C7 C 0.6370(3) 0.8993(3) 1.02176(12) 0.0291(6) Uani 1 1 d . . .
H7A H 0.6289 0.8416 1.0592 0.035 Uiso 1 1 calc R . .
H7B H 0.5806 0.9778 1.0311 0.035 Uiso 1 1 calc R . .
C8 C 0.5701(3) 0.8313(2) 0.96329(11) 0.0213(5) Uani 1 1 d . . .
H8 H 0.4712 0.8030 0.9758 0.026 Uiso 1 1 calc R . .
C9 C 0.5564(3) 0.9049(2) 0.89929(11) 0.0207(5) Uani 1 1 d . . .
H9 H 0.6470 0.9547 0.8920 0.025 Uiso 1 1 calc R . .
C10 C 0.5503(3) 0.7932(2) 0.85032(10) 0.0219(6) Uani 1 1 d . . .
H10 H 0.4492 0.7608 0.8480 0.026 Uiso 1 1 calc R . .
C11 C 0.6544(3) 0.7092(2) 0.94241(11) 0.0225(6) Uani 1 1 d . . .
C12 C 0.4267(3) 0.9982(3) 0.89367(12) 0.0266(6) Uani 1 1 d . . .
H12A H 0.4307 1.0608 0.9293 0.032 Uiso 1 1 calc R . .
H12B H 0.4350 1.0470 0.8532 0.032 Uiso 1 1 calc R . .
C13 C 0.6008(3) 0.8257(2) 0.78319(12) 0.0244(6) Uani 1 1 d . . .
C14 C 0.5136(3) 0.8244(3) 0.73095(12) 0.0308(7) Uani 1 1 d . . .
C15 C 0.5937(4) 0.8718(3) 0.67155(13) 0.0415(8) Uani 1 1 d . . .
H15A H 0.5399 0.9419 0.6503 0.050 Uiso 1 1 calc R . .
H15B H 0.6081 0.8008 0.6407 0.050 Uiso 1 1 calc R . .
C16 C 0.7399(4) 0.9211(3) 0.69734(14) 0.0474(8) Uani 1 1 d . . .
H16A H 0.7422 1.0162 0.6970 0.057 Uiso 1 1 calc R . .
H16B H 0.8197 0.8889 0.6704 0.057 Uiso 1 1 calc R . .
C17 C 0.7557(3) 0.8691(3) 0.76773(12) 0.0297(6) Uani 1 1 d . . .
H17 H 0.7821 0.9422 0.7965 0.036 Uiso 1 1 calc R . .
C18 C 0.8678(3) 0.7614(3) 0.77554(12) 0.0297(6) Uani 1 1 d . . .
C19 C 0.9898(3) 0.7783(4) 0.80811(13) 0.0444(8) Uani 1 1 d . . .
H19A H 1.0569 0.7099 0.8117 0.053 Uiso 1 1 calc R . .
H19B H 1.0094 0.8587 0.8277 0.053 Uiso 1 1 calc R . .
C20 C 0.8339(4) 0.6318(3) 0.74341(16) 0.0463(8) Uani 1 1 d . . .
H20A H 0.9159 0.5736 0.7485 0.070 Uiso 1 1 calc R . .
H20B H 0.8155 0.6457 0.6979 0.070 Uiso 1 1 calc R . .
H20C H 0.7486 0.5937 0.7634 0.070 Uiso 1 1 calc R . .
C21 C 0.3590(4) 0.7820(4) 0.72588(15) 0.0482(9) Uani 1 1 d . . .
H21A H 0.3252 0.7528 0.7678 0.072 Uiso 1 1 calc R . .
H21B H 0.3515 0.7114 0.6951 0.072 Uiso 1 1 calc R . .
H21C H 0.2998 0.8544 0.7115 0.072 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 0.0350(4) 0.0226(4) 0.0501(4) -0.0074(3) -0.0197(3) 0.0054(3)
O1 0.0386(11) 0.0202(10) 0.0349(10) 0.0057(8) -0.0093(8) 0.0023(8)
O2 0.0288(10) 0.0182(9) 0.0249(9) 0.0000(7) -0.0022(7) 0.0020(7)
O3 0.0235(10) 0.0544(13) 0.0277(10) 0.0045(9) 0.0017(7) 0.0053(10)
C1 0.0237(13) 0.0221(12) 0.0314(13) -0.0117(10) -0.0096(11) 0.0012(11)
C2 0.0222(15) 0.0393(17) 0.0440(16) -0.0219(14) 0.0001(13) 0.0006(12)
C3 0.0319(16) 0.0430(18) 0.0359(15) -0.0112(13) -0.0030(13) -0.0118(14)
C4 0.0350(16) 0.0295(14) 0.0324(14) -0.0021(12) -0.0069(13) -0.0086(13)
C5 0.0349(15) 0.0240(14) 0.0401(15) -0.0062(12) -0.0029(13) 0.0027(12)
C6 0.0265(14) 0.0290(15) 0.0330(14) -0.0092(12) 0.0039(11) -0.0001(11)
C7 0.0398(16) 0.0273(13) 0.0201(12) 0.0034(11) -0.0004(11) 0.0026(12)
C8 0.0182(12) 0.0215(12) 0.0242(12) 0.0048(10) -0.0011(10) -0.0007(10)
C9 0.0203(12) 0.0203(13) 0.0215(12) 0.0052(9) 0.0017(10) 0.0000(11)
C10 0.0197(13) 0.0207(13) 0.0254(13) 0.0040(10) -0.0017(10) -0.0002(11)
C11 0.0237(14) 0.0176(12) 0.0262(13) 0.0031(10) -0.0012(11) -0.0044(11)
C12 0.0307(15) 0.0276(13) 0.0217(12) 0.0047(10) 0.0043(11) 0.0061(12)
C13 0.0279(15) 0.0194(13) 0.0257(13) -0.0007(10) 0.0012(11) 0.0019(11)
C14 0.0394(16) 0.0284(15) 0.0246(13) -0.0007(12) -0.0042(12) 0.0041(13)
C15 0.064(2) 0.0370(17) 0.0231(13) 0.0032(12) 0.0040(14) 0.0009(16)
C16 0.060(2) 0.0425(19) 0.0395(17) 0.0126(14) 0.0171(16) 0.0023(17)
C17 0.0319(16) 0.0287(15) 0.0286(13) -0.0032(12) 0.0085(12) -0.0031(12)
C18 0.0247(15) 0.0347(15) 0.0297(14) -0.0056(12) 0.0089(11) -0.0016(12)
C19 0.0314(17) 0.057(2) 0.0450(18) -0.0078(16) 0.0029(14) 0.0007(15)
C20 0.0434(19) 0.0345(17) 0.061(2) -0.0168(15) 0.0092(16) -0.0015(15)
C21 0.044(2) 0.062(2) 0.0384(16) 0.0011(16) -0.0183(14) -0.0024(17)

_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 C1 1.756(3) . ?
S1 C7 1.814(3) . ?
O1 C11 1.208(3) . ?
O2 C11 1.322(3) . ?
O2 C10 1.471(3) . ?
O3 C12 1.423(3) . ?
O3 H3 0.8200 . ?
C1 C2 1.390(4) . ?
C1 C6 1.393(3) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.513(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.517(3) . ?
C8 C11 1.523(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.519(3) . ?
C9 C12 1.521(4) . ?
C9 H9 0.9800 . ?
C10 C13 1.489(3) . ?
C10 H10 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.334(4) . ?
C13 C17 1.512(4) . ?
C14 C21 1.476(4) . ?
C14 C15 1.500(4) . ?
C15 C16 1.519(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.545(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.507(4) . ?
C17 H17 0.9800 . ?
C18 C19 1.308(4) . ?
C18 C20 1.507(4) . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C1 S1 C7 103.97(13) . . ?
C11 O2 C10 109.35(18) . . ?
C12 O3 H3 109.5 . . ?
C2 C1 C6 118.4(3) . . ?
C2 C1 S1 119.1(2) . . ?
C6 C1 S1 122.4(2) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 S1 114.22(18) . . ?
C8 C7 H7A 108.7 . . ?
S1 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
S1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 C11 113.2(2) . . ?
C9 C8 C11 101.63(18) . . ?
C7 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C11 C8 H8 107.3 . . ?
C8 C9 C10 101.86(19) . . ?
C8 C9 C12 116.0(2) . . ?
C10 C9 C12 112.9(2) . . ?
C8 C9 H9 108.6 . . ?
C10 C9 H9 108.6 . . ?
C12 C9 H9 108.6 . . ?
O2 C10 C13 110.4(2) . . ?
O2 C10 C9 104.51(17) . . ?
C13 C10 C9 115.7(2) . . ?
O2 C10 H10 108.6 . . ?
C13 C10 H10 108.6 . . ?
C9 C10 H10 108.6 . . ?
O1 C11 O2 121.6(2) . . ?
O1 C11 C8 127.3(2) . . ?
O2 C11 C8 111.0(2) . . ?
O3 C12 C9 113.2(2) . . ?
O3 C12 H12A 108.9 . . ?
C9 C12 H12A 108.9 . . ?
O3 C12 H12B 108.9 . . ?
C9 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C10 123.8(2) . . ?
C14 C13 C17 113.0(2) . . ?
C10 C13 C17 123.2(2) . . ?
C13 C14 C21 128.9(3) . . ?
C13 C14 C15 111.1(3) . . ?
C21 C14 C15 120.1(3) . . ?
C14 C15 C16 104.5(2) . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C15 C16 C17 107.1(2) . . ?
C15 C16 H16A 110.3 . . ?
C17 C16 H16A 110.3 . . ?
C15 C16 H16B 110.3 . . ?
C17 C16 H16B 110.3 . . ?
H16A C16 H16B 108.5 . . ?
C18 C17 C13 113.4(2) . . ?
C18 C17 C16 114.3(2) . . ?
C13 C17 C16 102.1(2) . . ?
C18 C17 H17 108.9 . . ?
C13 C17 H17 108.9 . . ?
C16 C17 H17 108.9 . . ?
C19 C18 C20 120.9(3) . . ?
C19 C18 C17 122.3(3) . . ?
C20 C18 C17 116.9(2) . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C7 S1 C1 C2 -135.5(2) . . . . ?
C7 S1 C1 C6 48.6(2) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
S1 C1 C2 C3 -176.7(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
C4 C5 C6 C1 -1.7(4) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
S1 C1 C6 C5 177.1(2) . . . . ?
C1 S1 C7 C8 87.2(2) . . . . ?
S1 C7 C8 C9 -63.7(3) . . . . ?
S1 C7 C8 C11 55.9(2) . . . . ?
C7 C8 C9 C10 156.5(2) . . . . ?
C11 C8 C9 C10 31.2(2) . . . . ?
C7 C8 C9 C12 -80.5(3) . . . . ?
C11 C8 C9 C12 154.2(2) . . . . ?
C11 O2 C10 C13 146.8(2) . . . . ?
C11 O2 C10 C9 21.7(3) . . . . ?
C8 C9 C10 O2 -32.8(2) . . . . ?
C12 C9 C10 O2 -157.92(19) . . . . ?
C8 C9 C10 C13 -154.5(2) . . . . ?
C12 C9 C10 C13 80.4(3) . . . . ?
C10 O2 C11 O1 179.2(2) . . . . ?
C10 O2 C11 C8 -0.9(3) . . . . ?
C7 C8 C11 O1 30.5(4) . . . . ?
C9 C8 C11 O1 159.9(3) . . . . ?
C7 C8 C11 O2 -149.5(2) . . . . ?
C9 C8 C11 O2 -20.0(2) . . . . ?
C8 C9 C12 O3 -65.1(3) . . . . ?
C10 C9 C12 O3 51.9(3) . . . . ?
O2 C10 C13 C14 126.3(3) . . . . ?
C9 C10 C13 C14 -115.3(3) . . . . ?
O2 C10 C13 C17 -56.2(3) . . . . ?
C9 C10 C13 C17 62.2(3) . . . . ?
C10 C13 C14 C21 -5.6(5) . . . . ?
C17 C13 C14 C21 176.7(3) . . . . ?
C10 C13 C14 C15 175.5(2) . . . . ?
C17 C13 C14 C15 -2.2(3) . . . . ?
C13 C14 C15 C16 -7.6(3) . . . . ?
C21 C14 C15 C16 173.4(3) . . . . ?
C14 C15 C16 C17 14.0(3) . . . . ?
C14 C13 C17 C18 -112.7(3) . . . . ?
C10 C13 C17 C18 69.6(3) . . . . ?
C14 C13 C17 C16 10.8(3) . . . . ?
C10 C13 C17 C16 -167.0(2) . . . . ?
C15 C16 C17 C18 108.0(3) . . . . ?
C15 C16 C17 C13 -14.9(3) . . . . ?
C13 C17 C18 C19 -131.3(3) . . . . ?
C16 C17 C18 C19 112.2(3) . . . . ?
C13 C17 C18 C20 49.2(3) . . . . ?
C16 C17 C18 C20 -67.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.058

# Attachment '- r90607b-cif-for-6.cif'

data_r90607b
_database_code_depnum_ccdc_archive 'CCDC 869716'
#TrackingRef '- r90607b-cif-for-6.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H26 O3 S'
_chemical_formula_weight         358.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.1436(18)
_cell_length_b                   19.925(4)
_cell_length_c                   10.386(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.85(3)
_cell_angle_gamma                90.00
_cell_volume                     1858.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5364
_cell_measurement_theta_min      2.243
_cell_measurement_theta_max      27.476

_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    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_T_max  0.9774
_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            13690
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3255
_reflns_number_gt                2923
_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^)+(0.0566P)^2^+0.3298P] 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_number_reflns         3255
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.21295(5) 0.216827(18) 0.50349(4) 0.02580(14) Uani 1 1 d . . .
O1 O 0.31741(11) 0.30830(5) 0.16470(9) 0.0201(2) Uani 1 1 d . . .
O2 O 0.27283(13) 0.19977(5) 0.19421(10) 0.0276(3) Uani 1 1 d . . .
O3 O 0.67824(11) 0.35864(5) 0.45233(10) 0.0247(3) Uani 1 1 d . . .
H3 H 0.7256 0.3364 0.5124 0.037 Uiso 1 1 calc R . .
C1 C 0.34468(16) 0.42884(7) 0.19889(13) 0.0168(3) Uani 1 1 d . . .
C2 C 0.17925(16) 0.44501(7) 0.17087(13) 0.0184(3) Uani 1 1 d . . .
H2 H 0.1274 0.4130 0.1063 0.022 Uiso 1 1 calc R . .
C3 C 0.17758(18) 0.51562(7) 0.10646(15) 0.0242(3) Uani 1 1 d . . .
H3A H 0.1512 0.5120 0.0118 0.029 Uiso 1 1 calc R . .
H3B H 0.1059 0.5446 0.1369 0.029 Uiso 1 1 calc R . .
C4 C 0.33518(19) 0.54383(7) 0.14740(16) 0.0270(4) Uani 1 1 d . . .
H4A H 0.3665 0.5669 0.0750 0.032 Uiso 1 1 calc R . .
H4B H 0.3409 0.5746 0.2205 0.032 Uiso 1 1 calc R . .
C5 C 0.42885(17) 0.48239(7) 0.18652(14) 0.0216(3) Uani 1 1 d . . .
C6 C 0.59507(19) 0.48714(8) 0.21066(18) 0.0336(4) Uani 1 1 d . . .
H6A H 0.6373 0.4437 0.2337 0.050 Uiso 1 1 calc R . .
H6B H 0.6282 0.5180 0.2810 0.050 Uiso 1 1 calc R . .
H6C H 0.6263 0.5028 0.1327 0.050 Uiso 1 1 calc R . .
C7 C 0.10537(16) 0.44532(7) 0.29016(14) 0.0199(3) Uani 1 1 d . . .
C8 C 0.17916(18) 0.48419(8) 0.40702(14) 0.0268(4) Uani 1 1 d . . .
H8A H 0.1220 0.4802 0.4753 0.040 Uiso 1 1 calc R . .
H8B H 0.1855 0.5306 0.3836 0.040 Uiso 1 1 calc R . .
H8C H 0.2775 0.4668 0.4375 0.040 Uiso 1 1 calc R . .
C9 C -0.02447(17) 0.41430(8) 0.28607(16) 0.0274(4) Uani 1 1 d . . .
H9A H -0.0719 0.4165 0.3577 0.033 Uiso 1 1 calc R . .
H9B H -0.0676 0.3904 0.2116 0.033 Uiso 1 1 calc R . .
C10 C 0.40712(16) 0.36144(6) 0.24082(13) 0.0164(3) Uani 1 1 d . . .
H10 H 0.5083 0.3590 0.2225 0.020 Uiso 1 1 calc R . .
C11 C 0.41275(16) 0.33932(6) 0.38334(13) 0.0155(3) Uani 1 1 d . . .
H11 H 0.3164 0.3484 0.4082 0.019 Uiso 1 1 calc R . .
C12 C 0.43097(16) 0.26361(7) 0.36722(13) 0.0171(3) Uani 1 1 d . . .
H12 H 0.5338 0.2560 0.3561 0.020 Uiso 1 1 calc R . .
C13 C 0.33270(16) 0.25148(7) 0.23599(13) 0.0194(3) Uani 1 1 d . . .
C14 C 0.53531(16) 0.37347(7) 0.47982(14) 0.0201(3) Uani 1 1 d . . .
H14A H 0.5197 0.4216 0.4758 0.024 Uiso 1 1 calc R . .
H14B H 0.5308 0.3587 0.5680 0.024 Uiso 1 1 calc R . .
C15 C 0.40181(18) 0.21564(7) 0.47351(14) 0.0216(3) Uani 1 1 d . . .
H15A H 0.4692 0.2266 0.5545 0.026 Uiso 1 1 calc R . .
H15B H 0.4249 0.1704 0.4492 0.026 Uiso 1 1 calc R . .
C16 C 0.22034(17) 0.27728(7) 0.62991(14) 0.0200(3) Uani 1 1 d . . .
C17 C 0.32252(19) 0.27289(8) 0.74716(15) 0.0285(4) Uani 1 1 d . . .
H17 H 0.3945 0.2393 0.7587 0.034 Uiso 1 1 calc R . .
C18 C 0.3169(2) 0.31837(9) 0.84637(17) 0.0347(4) Uani 1 1 d . . .
H18 H 0.3863 0.3157 0.9241 0.042 Uiso 1 1 calc R . .
C19 C 0.2097(2) 0.36752(8) 0.83123(17) 0.0350(4) Uani 1 1 d . . .
H19 H 0.2053 0.3975 0.8990 0.042 Uiso 1 1 calc R . .
C20 C 0.1085(2) 0.37218(8) 0.71496(18) 0.0379(5) Uani 1 1 d . . .
H20 H 0.0362 0.4056 0.7042 0.045 Uiso 1 1 calc R . .
C21 C 0.11394(19) 0.32742(8) 0.61431(16) 0.0290(4) Uani 1 1 d . . .
H21 H 0.0459 0.3310 0.5359 0.035 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 0.0297(3) 0.0258(2) 0.0234(2) -0.00652(15) 0.00906(17) -0.01025(15)
O1 0.0257(6) 0.0183(5) 0.0151(5) -0.0026(4) 0.0004(4) -0.0004(4)
O2 0.0366(7) 0.0216(5) 0.0242(6) -0.0071(4) 0.0044(5) -0.0072(5)
O3 0.0172(6) 0.0308(6) 0.0243(6) 0.0057(5) -0.0005(4) 0.0000(4)
C1 0.0181(8) 0.0187(7) 0.0134(6) -0.0002(5) 0.0025(5) 0.0011(6)
C2 0.0183(8) 0.0177(7) 0.0177(7) -0.0018(6) -0.0003(6) 0.0019(5)
C3 0.0293(9) 0.0228(7) 0.0201(7) 0.0034(6) 0.0031(6) 0.0080(6)
C4 0.0361(10) 0.0184(7) 0.0256(8) 0.0034(6) 0.0038(7) -0.0005(6)
C5 0.0244(8) 0.0222(7) 0.0174(7) 0.0025(6) 0.0018(6) -0.0014(6)
C6 0.0255(9) 0.0335(9) 0.0415(10) 0.0069(8) 0.0054(8) -0.0091(7)
C7 0.0198(8) 0.0181(7) 0.0213(7) 0.0013(6) 0.0027(6) 0.0065(6)
C8 0.0267(9) 0.0317(8) 0.0221(8) -0.0060(7) 0.0052(7) 0.0038(7)
C9 0.0237(9) 0.0307(8) 0.0280(8) 0.0003(7) 0.0053(7) 0.0006(7)
C10 0.0155(7) 0.0171(7) 0.0165(7) -0.0024(5) 0.0026(6) -0.0013(5)
C11 0.0158(7) 0.0148(6) 0.0159(7) -0.0013(5) 0.0030(6) 0.0016(5)
C12 0.0196(8) 0.0151(6) 0.0169(7) -0.0012(6) 0.0043(6) 0.0015(5)
C13 0.0221(8) 0.0188(7) 0.0186(7) -0.0029(6) 0.0069(6) 0.0009(6)
C14 0.0215(8) 0.0185(7) 0.0189(7) -0.0019(6) -0.0002(6) 0.0005(6)
C15 0.0304(9) 0.0155(7) 0.0196(7) -0.0007(6) 0.0069(6) 0.0023(6)
C16 0.0224(8) 0.0195(7) 0.0200(7) 0.0009(6) 0.0088(6) -0.0044(6)
C17 0.0276(9) 0.0335(8) 0.0249(8) -0.0030(7) 0.0063(7) 0.0059(7)
C18 0.0316(10) 0.0487(10) 0.0255(9) -0.0105(8) 0.0098(7) -0.0096(8)
C19 0.0489(11) 0.0270(8) 0.0378(10) -0.0118(7) 0.0305(9) -0.0135(8)
C20 0.0525(12) 0.0237(8) 0.0463(11) 0.0075(8) 0.0318(10) 0.0119(8)
C21 0.0302(9) 0.0327(8) 0.0265(8) 0.0091(7) 0.0116(7) 0.0059(7)

_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 C16 1.7737(14) . ?
S1 C15 1.8116(16) . ?
O1 C13 1.3455(17) . ?
O1 C10 1.4748(17) . ?
O2 C13 1.2085(17) . ?
O3 C14 1.4203(17) . ?
O3 H3 0.8200 . ?
C1 C5 1.336(2) . ?
C1 C10 1.4919(18) . ?
C1 C2 1.520(2) . ?
C2 C7 1.519(2) . ?
C2 C3 1.5566(19) . ?
C2 H2 0.9800 . ?
C3 C4 1.531(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.505(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.496(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C9 1.332(2) . ?
C7 C8 1.490(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C10 C11 1.5360(19) . ?
C10 H10 0.9800 . ?
C11 C14 1.517(2) . ?
C11 C12 1.5304(18) . ?
C11 H11 0.9800 . ?
C12 C13 1.504(2) . ?
C12 C15 1.5213(19) . ?
C12 H12 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C21 1.383(2) . ?
C16 C17 1.391(2) . ?
C17 C18 1.380(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 S1 C15 103.38(7) . . ?
C13 O1 C10 108.62(10) . . ?
C14 O3 H3 109.5 . . ?
C5 C1 C10 123.46(13) . . ?
C5 C1 C2 112.50(12) . . ?
C10 C1 C2 123.99(12) . . ?
C7 C2 C1 115.09(12) . . ?
C7 C2 C3 112.15(11) . . ?
C1 C2 C3 101.70(11) . . ?
C7 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C4 C3 C2 106.26(12) . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
C5 C4 C3 103.56(12) . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C1 C5 C6 128.30(14) . . ?
C1 C5 C4 111.51(14) . . ?
C6 C5 C4 120.15(13) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C7 C8 122.10(14) . . ?
C9 C7 C2 120.18(14) . . ?
C8 C7 C2 117.64(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 120.0 . . ?
C7 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
O1 C10 C1 110.25(11) . . ?
O1 C10 C11 103.01(10) . . ?
C1 C10 C11 118.76(11) . . ?
O1 C10 H10 108.1 . . ?
C1 C10 H10 108.1 . . ?
C11 C10 H10 108.1 . . ?
C14 C11 C12 115.62(12) . . ?
C14 C11 C10 113.25(11) . . ?
C12 C11 C10 99.32(10) . . ?
C14 C11 H11 109.4 . . ?
C12 C11 H11 109.4 . . ?
C10 C11 H11 109.4 . . ?
C13 C12 C15 113.59(12) . . ?
C13 C12 C11 101.46(11) . . ?
C15 C12 C11 120.16(11) . . ?
C13 C12 H12 106.9 . . ?
C15 C12 H12 106.9 . . ?
C11 C12 H12 106.9 . . ?
O2 C13 O1 121.78(13) . . ?
O2 C13 C12 127.98(13) . . ?
O1 C13 C12 110.24(11) . . ?
O3 C14 C11 111.55(11) . . ?
O3 C14 H14A 109.3 . . ?
C11 C14 H14A 109.3 . . ?
O3 C14 H14B 109.3 . . ?
C11 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C12 C15 S1 114.80(11) . . ?
C12 C15 H15A 108.6 . . ?
S1 C15 H15A 108.6 . . ?
C12 C15 H15B 108.6 . . ?
S1 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C21 C16 C17 119.33(14) . . ?
C21 C16 S1 118.43(12) . . ?
C17 C16 S1 122.07(11) . . ?
C18 C17 C16 119.93(15) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.57(17) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.66(15) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 120.34(16) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.16(16) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?

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
C5 C1 C2 C7 -108.51(14) . . . . ?
C10 C1 C2 C7 69.17(16) . . . . ?
C5 C1 C2 C3 12.96(15) . . . . ?
C10 C1 C2 C3 -169.36(12) . . . . ?
C7 C2 C3 C4 103.42(14) . . . . ?
C1 C2 C3 C4 -20.07(14) . . . . ?
C2 C3 C4 C5 20.24(15) . . . . ?
C10 C1 C5 C6 -0.2(2) . . . . ?
C2 C1 C5 C6 177.52(14) . . . . ?
C10 C1 C5 C4 -178.00(12) . . . . ?
C2 C1 C5 C4 -0.31(17) . . . . ?
C3 C4 C5 C1 -12.81(16) . . . . ?
C3 C4 C5 C6 169.17(13) . . . . ?
C1 C2 C7 C9 -133.95(14) . . . . ?
C3 C2 C7 C9 110.44(15) . . . . ?
C1 C2 C7 C8 49.20(17) . . . . ?
C3 C2 C7 C8 -66.41(17) . . . . ?
C13 O1 C10 C1 -154.42(11) . . . . ?
C13 O1 C10 C11 -26.72(13) . . . . ?
C5 C1 C10 O1 -140.44(13) . . . . ?
C2 C1 C10 O1 42.13(17) . . . . ?
C5 C1 C10 C11 101.12(17) . . . . ?
C2 C1 C10 C11 -76.31(17) . . . . ?
O1 C10 C11 C14 162.70(11) . . . . ?
C1 C10 C11 C14 -75.16(16) . . . . ?
O1 C10 C11 C12 39.51(12) . . . . ?
C1 C10 C11 C12 161.65(12) . . . . ?
C14 C11 C12 C13 -159.18(12) . . . . ?
C10 C11 C12 C13 -37.69(13) . . . . ?
C14 C11 C12 C15 74.66(17) . . . . ?
C10 C11 C12 C15 -163.86(13) . . . . ?
C10 O1 C13 O2 -178.26(13) . . . . ?
C10 O1 C13 C12 1.67(14) . . . . ?
C15 C12 C13 O2 -25.7(2) . . . . ?
C11 C12 C13 O2 -156.09(14) . . . . ?
C15 C12 C13 O1 154.38(11) . . . . ?
C11 C12 C13 O1 23.99(14) . . . . ?
C12 C11 C14 O3 52.63(16) . . . . ?
C10 C11 C14 O3 -61.03(15) . . . . ?
C13 C12 C15 S1 -58.37(14) . . . . ?
C11 C12 C15 S1 61.93(16) . . . . ?
C16 S1 C15 C12 -91.69(11) . . . . ?
C15 S1 C16 C21 130.15(12) . . . . ?
C15 S1 C16 C17 -54.55(14) . . . . ?
C21 C16 C17 C18 0.0(2) . . . . ?
S1 C16 C17 C18 -175.27(12) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 C18 C19 C20 -1.2(2) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?
C19 C20 C21 C16 0.5(2) . . . . ?
C17 C16 C21 C20 -0.7(2) . . . . ?
S1 C16 C21 C20 174.73(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.045