# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2006

data_global

_journal_coden_Cambridge         440

_publ_requested_journal          'New Journal of Chemistry'

loop_
_publ_author_name
J.Wallis
'Peter Day'
'Jon-Paul Griffiths'
'Hui Nie.'
'Qiang Wang.'

_publ_contact_author_name        'John Wallis'
_publ_contact_author_address     
;
School of Biomedical and Natural Sciences
The Nottingham Trent University
Clifton Lane
Nottingham
NG11 8NS
UNITED KINGDOM
;

_publ_contact_author_email       JOHN.WALLIS@NTU.AC.UK

_publ_section_title              
;
Synthetic Strategies for Preparing BEDT-TTF
Derivatives Functionalised With Metal Ion Binding Groups
;
# Attachment 'WANG_SYNTHESIS_CIFS_revised.txt'

data_c:\2005qw~1\qwe228
_database_code_depnum_ccdc_archive 'CCDC 616013'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          453-456
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20.50 H18 Cl N O2 S9'
_chemical_formula_weight         634.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8542(1)
_cell_length_b                   11.9820(2)
_cell_length_c                   14.1992(3)
_cell_angle_alpha                90.439(1)
_cell_angle_beta                 92.745(1)
_cell_angle_gamma                101.822(1)
_cell_volume                     1306.22(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5966
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             650
_exptl_absorpt_coefficient_mu    0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31614
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.52
_reflns_number_total             5986
_reflns_number_gt                5172
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
There is a dichloromethane molecule located close to a centre of symmetry,
such that the two Cl atoms are related by the centre, but there are two
possible positions, related by the centre, for the methylene group. There
is probably further disorder in the orientation of this solvent molecule.

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^)+(0.0306P)^2^+2.2279P] 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         5986
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
Cl1 Cl 0.00617(15) -0.37243(12) 1.00614(7) 0.0757(3) Uani 1 1 d . . .
S1 S 0.24710(8) 0.47814(5) 0.48052(4) 0.01995(13) Uani 1 1 d . . .
S2 S 0.21450(8) 0.58888(5) 0.69954(4) 0.02036(13) Uani 1 1 d . . .
S3 S 0.21343(7) 0.25587(5) 0.57651(4) 0.01723(12) Uani 1 1 d . . .
S4 S 0.15715(8) 0.34678(5) 0.76335(4) 0.02202(13) Uani 1 1 d . . .
S5 S 0.04104(8) 0.00285(5) 0.63755(4) 0.01991(13) Uani 1 1 d . . .
S6 S -0.02668(8) 0.08849(5) 0.82538(4) 0.02154(13) Uani 1 1 d . . .
S7 S -0.14625(8) -0.23249(5) 0.66498(4) 0.02246(13) Uani 1 1 d . . .
S8 S -0.22217(8) -0.13158(5) 0.88984(4) 0.02481(14) Uani 1 1 d . . .
S9 S 0.30781(8) 0.84936(5) 0.47262(4) 0.02184(13) Uani 1 1 d . . .
O1 O 0.3461(3) 0.56731(15) 0.17547(14) 0.0380(5) Uani 1 1 d . . .
O2 O 0.6479(3) 1.15317(14) 0.24640(13) 0.0311(4) Uani 1 1 d . . .
N1 N 0.5126(2) 0.86402(16) 0.17571(13) 0.0186(4) Uani 1 1 d . . .
C1 C 0.3364(3) 0.62676(19) 0.51819(16) 0.0182(4) Uani 1 1 d . . .
H1 H 0.4431 0.6538 0.4823 0.022 Uiso 1 1 calc R . .
C2 C 0.3914(3) 0.6402(2) 0.62224(16) 0.0200(5) Uani 1 1 d . . .
H2B H 0.4393 0.7218 0.6369 0.024 Uiso 1 1 calc R . .
H2A H 0.4856 0.5980 0.6355 0.024 Uiso 1 1 calc R . .
C3 C 0.2131(3) 0.40306(18) 0.58501(16) 0.0165(4) Uani 1 1 d . . .
C4 C 0.1902(3) 0.44454(18) 0.67072(16) 0.0174(4) Uani 1 1 d . . .
C5 C 0.1259(3) 0.22699(19) 0.68746(16) 0.0185(4) Uani 1 1 d . . .
C6 C 0.0518(3) 0.12100(19) 0.71282(15) 0.0176(4) Uani 1 1 d . . .
C7 C -0.0861(3) -0.09335(19) 0.71125(15) 0.0171(4) Uani 1 1 d . . .
C8 C -0.1163(3) -0.05608(19) 0.79710(16) 0.0178(4) Uani 1 1 d . . .
C9 C -0.1640(3) -0.3089(2) 0.77407(17) 0.0229(5) Uani 1 1 d . . .
H9A H -0.1996 -0.3917 0.7599 0.028 Uiso 1 1 calc R . .
H9B H -0.0483 -0.2953 0.8080 0.028 Uiso 1 1 calc R . .
C10 C -0.2948(3) -0.2733(2) 0.83752(17) 0.0237(5) Uani 1 1 d . . .
H10A H -0.3190 -0.3291 0.8887 0.028 Uiso 1 1 calc R . .
H10B H -0.4053 -0.2757 0.8002 0.028 Uiso 1 1 calc R . .
C11 C 0.2056(3) 0.70135(19) 0.48946(17) 0.0202(5) Uani 1 1 d . . .
H11B H 0.1198 0.6974 0.5388 0.024 Uiso 1 1 calc R . .
H11A H 0.1415 0.6702 0.4301 0.024 Uiso 1 1 calc R . .
C22 C 0.4308(3) 0.76442(19) 0.21009(16) 0.0188(5) Uani 1 1 d . . .
C23 C 0.3634(3) 0.75200(19) 0.29920(16) 0.0190(5) Uani 1 1 d . . .
H23 H 0.3065 0.6792 0.3198 0.023 Uiso 1 1 calc R . .
C24 C 0.3807(3) 0.84816(19) 0.35780(15) 0.0178(4) Uani 1 1 d . . .
C25 C 0.4653(3) 0.95280(19) 0.32239(16) 0.0191(5) Uani 1 1 d . . .
H25 H 0.4795 1.0207 0.3595 0.023 Uiso 1 1 calc R . .
C26 C 0.5282(3) 0.95609(19) 0.23264(16) 0.0185(4) Uani 1 1 d . . .
C27 C 0.4164(3) 0.6603(2) 0.14801(17) 0.0246(5) Uani 1 1 d . . .
C28 C 0.4908(4) 0.6762(2) 0.05263(18) 0.0287(6) Uani 1 1 d . . .
H28C H 0.4806 0.6017 0.0215 0.043 Uiso 1 1 calc R . .
H28B H 0.6139 0.7141 0.0596 0.043 Uiso 1 1 calc R . .
H28A H 0.4267 0.7232 0.0144 0.043 Uiso 1 1 calc R . .
C29 C 0.6232(3) 1.06858(19) 0.19571(17) 0.0206(5) Uani 1 1 d . . .
C30 C 0.6855(3) 1.0718(2) 0.09738(17) 0.0238(5) Uani 1 1 d . . .
H30C H 0.5861 1.0668 0.0520 0.036 Uiso 1 1 calc R . .
H30A H 0.7422 1.0074 0.0871 0.036 Uiso 1 1 calc R . .
H30B H 0.7690 1.1435 0.0888 0.036 Uiso 1 1 calc R . .
C40 C -0.0430(9) -0.5129(9) 1.0548(4) 0.070(3) Uani 0.50 1 d P . .
H40A H 0.0234 -0.5095 1.1161 0.084 Uiso 0.50 1 calc PR . .
H40B H -0.1680 -0.5290 1.0685 0.084 Uiso 0.50 1 calc PR . .

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
Cl1 0.0706(7) 0.1170(10) 0.0472(5) 0.0039(6) 0.0008(5) 0.0378(7)
S1 0.0284(3) 0.0138(3) 0.0162(3) -0.0006(2) 0.0013(2) 0.0008(2)
S2 0.0270(3) 0.0141(3) 0.0197(3) -0.0018(2) 0.0072(2) 0.0024(2)
S3 0.0203(3) 0.0134(3) 0.0181(3) 0.0006(2) 0.0032(2) 0.0032(2)
S4 0.0318(3) 0.0162(3) 0.0167(3) -0.0004(2) 0.0031(2) 0.0015(2)
S5 0.0290(3) 0.0139(3) 0.0170(3) 0.0015(2) 0.0068(2) 0.0033(2)
S6 0.0320(3) 0.0155(3) 0.0166(3) -0.0002(2) 0.0042(2) 0.0030(2)
S7 0.0327(3) 0.0153(3) 0.0174(3) -0.0008(2) 0.0052(2) -0.0007(2)
S8 0.0330(3) 0.0214(3) 0.0186(3) 0.0005(2) 0.0103(2) 0.0001(2)
S9 0.0304(3) 0.0176(3) 0.0187(3) 0.0014(2) 0.0046(2) 0.0069(2)
O1 0.0603(13) 0.0161(9) 0.0329(10) -0.0025(8) 0.0139(9) -0.0058(9)
O2 0.0470(11) 0.0136(8) 0.0299(10) -0.0012(7) 0.0032(8) -0.0006(8)
N1 0.0203(10) 0.0140(9) 0.0208(9) 0.0013(7) 0.0005(8) 0.0018(7)
C1 0.0203(11) 0.0142(10) 0.0191(11) -0.0002(8) 0.0040(9) 0.0003(8)
C2 0.0213(11) 0.0164(11) 0.0209(11) -0.0021(9) 0.0030(9) 0.0000(9)
C3 0.0166(10) 0.0115(10) 0.0206(11) 0.0009(8) 0.0011(8) 0.0008(8)
C4 0.0199(11) 0.0126(10) 0.0191(11) 0.0003(8) 0.0017(9) 0.0018(8)
C5 0.0212(11) 0.0177(11) 0.0167(10) -0.0004(8) 0.0014(9) 0.0042(9)
C6 0.0216(11) 0.0163(11) 0.0153(10) 0.0017(8) 0.0012(8) 0.0052(9)
C7 0.0190(11) 0.0150(11) 0.0170(10) 0.0015(8) 0.0022(8) 0.0020(8)
C8 0.0203(11) 0.0152(11) 0.0177(10) 0.0025(8) 0.0032(9) 0.0024(9)
C9 0.0324(13) 0.0162(11) 0.0205(11) 0.0040(9) 0.0074(10) 0.0042(10)
C10 0.0315(13) 0.0167(11) 0.0218(11) 0.0023(9) 0.0089(10) 0.0008(10)
C11 0.0186(11) 0.0192(11) 0.0228(11) 0.0041(9) 0.0039(9) 0.0035(9)
C22 0.0206(11) 0.0146(11) 0.0209(11) -0.0009(9) 0.0003(9) 0.0028(9)
C23 0.0205(11) 0.0134(10) 0.0224(11) 0.0030(9) 0.0002(9) 0.0020(9)
C24 0.0185(11) 0.0180(11) 0.0175(10) 0.0012(9) 0.0001(8) 0.0055(9)
C25 0.0230(11) 0.0139(11) 0.0207(11) -0.0004(9) -0.0014(9) 0.0047(9)
C26 0.0192(11) 0.0144(11) 0.0217(11) 0.0006(9) -0.0018(9) 0.0033(9)
C27 0.0306(13) 0.0166(12) 0.0253(12) -0.0011(9) 0.0025(10) 0.0020(10)
C28 0.0437(16) 0.0187(12) 0.0231(12) -0.0023(10) 0.0068(11) 0.0037(11)
C29 0.0226(12) 0.0145(11) 0.0239(12) 0.0035(9) -0.0016(9) 0.0027(9)
C30 0.0255(12) 0.0170(11) 0.0273(12) 0.0038(10) 0.0039(10) 0.0002(9)
C40 0.030(3) 0.168(9) 0.016(3) 0.012(4) 0.000(2) 0.031(4)

_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
Cl1 C40 1.699(9) 2_547 ?
Cl1 C40 1.799(10) . ?
S1 C3 1.744(2) . ?
S1 C1 1.840(2) . ?
S2 C4 1.744(2) . ?
S2 C2 1.822(2) . ?
S3 C5 1.758(2) . ?
S3 C3 1.767(2) . ?
S4 C5 1.757(2) . ?
S4 C4 1.761(2) . ?
S5 C7 1.752(2) . ?
S5 C6 1.753(2) . ?
S6 C6 1.758(2) . ?
S6 C8 1.766(2) . ?
S7 C7 1.751(2) . ?
S7 C9 1.802(2) . ?
S8 C8 1.749(2) . ?
S8 C10 1.817(2) . ?
S9 C24 1.755(2) . ?
S9 C11 1.813(2) . ?
O1 C27 1.214(3) . ?
O2 C29 1.216(3) . ?
N1 C22 1.342(3) . ?
N1 C26 1.344(3) . ?
C1 C2 1.517(3) . ?
C1 C11 1.537(3) . ?
C3 C4 1.345(3) . ?
C5 C6 1.344(3) . ?
C7 C8 1.343(3) . ?
C9 C10 1.521(3) . ?
C22 C23 1.392(3) . ?
C22 C27 1.504(3) . ?
C23 C24 1.396(3) . ?
C24 C25 1.402(3) . ?
C25 C26 1.386(3) . ?
C26 C29 1.512(3) . ?
C27 C28 1.499(3) . ?
C29 C30 1.500(3) . ?
C40 Cl1 1.699(9) 2_547 ?

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
C40 Cl1 C40 59.2(3) 2_547 . ?
C3 S1 C1 104.96(10) . . ?
C4 S2 C2 96.47(11) . . ?
C5 S3 C3 93.45(10) . . ?
C5 S4 C4 93.70(11) . . ?
C7 S5 C6 94.55(10) . . ?
C6 S6 C8 94.69(10) . . ?
C7 S7 C9 98.83(11) . . ?
C8 S8 C10 101.90(11) . . ?
C24 S9 C11 102.88(11) . . ?
C22 N1 C26 116.33(19) . . ?
C2 C1 C11 112.08(19) . . ?
C2 C1 S1 113.59(16) . . ?
C11 C1 S1 109.43(15) . . ?
C1 C2 S2 113.54(16) . . ?
C4 C3 S1 127.62(17) . . ?
C4 C3 S3 116.85(17) . . ?
S1 C3 S3 115.52(12) . . ?
C3 C4 S2 124.91(18) . . ?
C3 C4 S4 117.15(17) . . ?
S2 C4 S4 117.54(13) . . ?
C6 C5 S4 123.71(18) . . ?
C6 C5 S3 122.21(17) . . ?
S4 C5 S3 113.96(13) . . ?
C5 C6 S5 121.68(17) . . ?
C5 C6 S6 123.20(17) . . ?
S5 C6 S6 114.97(13) . . ?
C8 C7 S7 127.55(18) . . ?
C8 C7 S5 118.16(17) . . ?
S7 C7 S5 114.12(12) . . ?
C7 C8 S8 129.61(18) . . ?
C7 C8 S6 116.58(17) . . ?
S8 C8 S6 113.69(12) . . ?
C10 C9 S7 112.54(17) . . ?
C9 C10 S8 113.75(17) . . ?
C1 C11 S9 113.14(16) . . ?
N1 C22 C23 124.2(2) . . ?
N1 C22 C27 116.8(2) . . ?
C23 C22 C27 118.9(2) . . ?
C22 C23 C24 119.0(2) . . ?
C23 C24 C25 117.3(2) . . ?
C23 C24 S9 125.66(18) . . ?
C25 C24 S9 117.03(17) . . ?
C26 C25 C24 119.3(2) . . ?
N1 C26 C25 123.9(2) . . ?
N1 C26 C29 117.0(2) . . ?
C25 C26 C29 119.1(2) . . ?
O1 C27 C28 122.1(2) . . ?
O1 C27 C22 120.1(2) . . ?
C28 C27 C22 117.8(2) . . ?
O2 C29 C30 122.0(2) . . ?
O2 C29 C26 119.3(2) . . ?
C30 C29 C26 118.6(2) . . ?
Cl1 C40 Cl1 120.8(3) 2_547 . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.322
_refine_diff_density_min         -1.149
_refine_diff_density_rms         0.079

#===END

data_c:\2005sr~2\tosylz2
_database_code_depnum_ccdc_archive 'CCDC 616014'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Tosyloxymethyl-ET
;
_chemical_name_common            ?
_chemical_melting_point          333-335
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 O3 S9'
_chemical_formula_weight         568.85

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2490(1)
_cell_length_b                   11.0486(3)
_cell_length_c                   16.4757(4)
_cell_angle_alpha                82.167(2)
_cell_angle_beta                 82.328(2)
_cell_angle_gamma                87.627(2)
_cell_volume                     1116.51(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4972
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.48

_exptl_crystal_description       slab
_exptl_crystal_colour            'pale brown'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         
;
Bruker-Nonius FR591 rotating anode
;
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23783
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         27.56
_reflns_number_total             5112
_reflns_number_gt                4480
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
The structure is disordered between two forms: 87:13. The major form is
well characterised in the model, but the minor form is represented only by the
S and O atoms and selected C atoms where their positions deviate notably
from the other form (and could be located). The difference between the two
structures relates to which C of the ethylene bridge the tosyloxymethyl
sidechain is attached to.

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^)+(0.0578P)^2^+0.9914P] 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         5112
_refine_ls_number_parameters     341
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.003
_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 -0.03486(10) 0.94650(7) 0.33952(4) 0.02469(19) Uani 0.8702(17) 1 d P A 1
S2 S 0.48085(10) 0.98189(7) 0.22131(5) 0.02564(18) Uani 0.8702(17) 1 d P A 1
S3 S -0.09498(12) 0.76907(9) 0.22550(7) 0.02774(19) Uani 0.8702(17) 1 d P A 1
S4 S 0.34201(16) 0.78931(8) 0.13328(6) 0.02601(19) Uani 0.8702(17) 1 d P A 1
S5 S -0.15659(14) 0.51078(10) 0.16065(9) 0.0302(2) Uani 0.8702(17) 1 d P A 1
S6 S 0.2764(2) 0.52595(9) 0.06623(7) 0.0258(2) Uani 0.8702(17) 1 d P A 1
S7 S -0.17173(16) 0.23810(9) 0.16734(6) 0.0344(2) Uani 0.8702(17) 1 d P A 1
S8 S 0.3210(2) 0.25311(13) 0.06371(10) 0.0270(3) Uani 0.8702(17) 1 d P A 1
S9 S 0.33158(13) 0.77305(6) 0.53400(4) 0.02702(19) Uani 0.8702(17) 1 d P A 1
O1 O 0.2288(3) 0.89293(17) 0.48907(11) 0.0268(4) Uani 0.8702(17) 1 d P A 1
O2 O 0.5518(4) 0.79339(19) 0.54234(14) 0.0341(5) Uani 0.8702(17) 1 d P A 1
O3 O 0.1819(4) 0.7419(2) 0.60628(12) 0.0383(5) Uani 0.8702(17) 1 d P A 1
C1 C 0.1982(4) 1.0244(2) 0.36088(15) 0.0219(5) Uani 0.8702(17) 1 d P A 1
H1 H 0.1421 1.0896 0.3953 0.026 Uiso 0.8702(17) 1 calc PR A 1
C2 C 0.3258(4) 1.0878(2) 0.28198(17) 0.0246(5) Uani 0.8702(17) 1 d P A 1
H2A H 0.4252 1.1462 0.2970 0.029 Uiso 0.8702(17) 1 calc PR A 1
H2B H 0.2241 1.1351 0.2479 0.029 Uiso 0.8702(17) 1 calc PR A 1
C3 C 0.0784(4) 0.8727(2) 0.25511(14) 0.0248(5) Uani 1 1 d . A 1
C4 C 0.2774(4) 0.8809(2) 0.21410(14) 0.0237(4) Uani 1 1 d . A 1
C5 C 0.1122(4) 0.7009(2) 0.16189(14) 0.0253(5) Uani 1 1 d . A 1
C6 C 0.0856(4) 0.5935(2) 0.13429(14) 0.0252(5) Uani 1 1 d . A 1
C7 C -0.0297(4) 0.3737(2) 0.13621(15) 0.0275(5) Uani 1 1 d . A 1
C8 C 0.1696(4) 0.3786(2) 0.09463(13) 0.0235(4) Uani 1 1 d . A 1
C9 C -0.1021(6) 0.1695(5) 0.0725(3) 0.0532(11) Uani 0.8702(17) 1 d P A 1
H9A H -0.1451 0.0830 0.0849 0.064 Uiso 1 1 calc R A 1
H9B H -0.1954 0.2100 0.0322 0.064 Uiso 1 1 calc R A 1
C10 C 0.1093(7) 0.1703(5) 0.0319(3) 0.0596(13) Uani 0.8702(17) 1 d P A 1
H10A H 0.1007 0.2014 -0.0269 0.071 Uiso 1 1 calc R A 1
H10B H 0.1597 0.0839 0.0337 0.071 Uiso 1 1 calc R A 1
C11 C 0.3480(6) 0.9418(3) 0.40983(18) 0.0259(6) Uani 0.8702(17) 1 d P A 1
H11A H 0.4038 0.8740 0.3788 0.031 Uiso 0.8702(17) 1 calc PR A 1
H11B H 0.4724 0.9886 0.4191 0.031 Uiso 0.8702(17) 1 calc PR A 1
C12 C 0.3309(4) 0.6690(2) 0.46319(15) 0.0314(5) Uani 1 1 d . A 1
C13 C 0.5216(5) 0.6253(3) 0.4236(2) 0.0452(7) Uani 1 1 d . A 1
H13 H 0.6569 0.6518 0.4340 0.054 Uiso 1 1 calc R A 1
C14 C 0.5121(5) 0.5417(3) 0.36814(18) 0.0428(7) Uani 1 1 d . A 1
H14 H 0.6423 0.5114 0.3404 0.051 Uiso 1 1 calc R A 1
C15 C 0.3171(4) 0.5024(2) 0.35297(14) 0.0292(5) Uani 1 1 d . A 1
C16 C 0.1315(5) 0.5507(3) 0.3924(2) 0.0472(7) Uani 1 1 d . A 1
H16 H -0.0044 0.5260 0.3814 0.057 Uiso 1 1 calc R A 1
C17 C 0.1363(5) 0.6336(3) 0.4472(2) 0.0470(7) Uani 1 1 d . A 1
H17 H 0.0058 0.6657 0.4736 0.056 Uiso 1 1 calc R A 1
C18 C 0.3100(5) 0.4090(2) 0.29547(17) 0.0422(7) Uani 1 1 d . A 1
H18A H 0.3423 0.4478 0.2382 0.063 Uiso 1 1 calc R A 1
H18B H 0.1657 0.3742 0.3037 0.063 Uiso 1 1 calc R A 1
H18C H 0.4173 0.3438 0.3068 0.063 Uiso 1 1 calc R A 1
S1A S -0.0788(7) 0.9928(4) 0.3002(3) 0.0221(11) Uiso 0.1298(17) 1 d P A 2
S2A S 0.4876(7) 0.9453(5) 0.2596(4) 0.0236(11) Uiso 0.1298(17) 1 d P A 2
S3A S -0.0944(10) 0.7945(6) 0.1951(4) 0.0244(15) Uiso 0.1298(17) 1 d P A 2
S4A S 0.3782(10) 0.7691(6) 0.1543(4) 0.0212(16) Uiso 0.1298(17) 1 d P A 2
S5A S -0.1489(12) 0.5318(7) 0.1341(4) 0.0243(18) Uiso 0.1298(17) 1 d P A 2
S6A S 0.3199(13) 0.5152(8) 0.0816(5) 0.023(2) Uiso 0.1298(17) 1 d P A 2
S7A S -0.2223(9) 0.2666(5) 0.1419(4) 0.0232(13) Uiso 0.1298(17) 1 d PD A 2
S8A S 0.3046(19) 0.2631(10) 0.0464(6) 0.025(3) Uiso 0.1298(17) 1 d PD A 2
S9A S 0.4505(10) 0.7992(4) 0.5119(3) 0.0243(11) Uiso 0.1298(17) 1 d PD A 2
O1A O 0.4681(18) 0.9207(8) 0.4486(6) 0.022(3) Uiso 0.1298(17) 1 d PD A 2
O2A O 0.660(3) 0.7728(14) 0.5355(9) 0.032(4) Uiso 0.1298(17) 1 d P A 2
O3A O 0.259(2) 0.8107(14) 0.5762(9) 0.033(3) Uiso 0.1298(17) 1 d P A 2
C1A C 0.129(3) 1.1009(15) 0.2971(10) 0.019(3) Uiso 0.1298(17) 1 d P A 2
C2A C 0.334(3) 1.0412(16) 0.3289(11) 0.018(3) Uiso 0.1298(17) 1 d P A 2
C9A C -0.082(3) 0.1338(12) 0.1054(11) 0.018(4) Uiso 0.1298(17) 1 d PD A 2
C10A C 0.127(2) 0.1378(13) 0.0566(10) 0.004(3) Uiso 0.1298(17) 1 d PD A 2
C11A C 0.276(3) 0.971(2) 0.4131(15) 0.029(6) Uiso 0.1298(17) 1 d PD A 2

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 0.0197(3) 0.0293(4) 0.0265(4) -0.0143(3) 0.0024(2) -0.0009(3)
S2 0.0247(3) 0.0196(3) 0.0316(4) -0.0091(3) 0.0065(3) -0.0028(2)
S3 0.0214(4) 0.0285(4) 0.0364(5) -0.0183(4) -0.0010(3) 0.0008(3)
S4 0.0308(4) 0.0228(4) 0.0240(4) -0.0102(3) 0.0052(4) -0.0003(3)
S5 0.0208(4) 0.0299(5) 0.0436(6) -0.0196(5) -0.0034(4) 0.0014(3)
S6 0.0333(5) 0.0200(4) 0.0230(5) -0.0077(3) 0.0051(4) 0.0000(4)
S7 0.0356(4) 0.0338(4) 0.0345(5) -0.0135(4) 0.0061(4) -0.0123(4)
S8 0.0270(5) 0.0227(5) 0.0315(7) -0.0094(5) -0.0003(5) 0.0042(3)
S9 0.0363(4) 0.0225(3) 0.0238(3) -0.0067(3) -0.0066(3) 0.0024(3)
O1 0.0317(10) 0.0237(9) 0.0242(9) -0.0040(7) -0.0008(7) 0.0025(7)
O2 0.0393(14) 0.0290(11) 0.0393(12) -0.0110(9) -0.0185(11) 0.0020(10)
O3 0.0576(14) 0.0309(11) 0.0236(10) -0.0042(8) 0.0039(9) 0.0031(10)
C1 0.0229(13) 0.0197(12) 0.0238(12) -0.0068(10) -0.0014(10) 0.0004(9)
C2 0.0301(14) 0.0166(12) 0.0262(13) -0.0058(10) 0.0017(10) 0.0019(10)
C3 0.0235(11) 0.0237(11) 0.0284(11) -0.0122(9) 0.0008(9) 0.0002(8)
C4 0.0289(11) 0.0179(10) 0.0242(10) -0.0077(8) 0.0014(9) 0.0002(8)
C5 0.0264(11) 0.0239(11) 0.0268(11) -0.0089(9) -0.0029(9) 0.0029(9)
C6 0.0271(11) 0.0248(11) 0.0253(11) -0.0109(9) -0.0036(9) 0.0052(9)
C7 0.0262(11) 0.0257(12) 0.0328(12) -0.0120(10) -0.0034(9) -0.0010(9)
C8 0.0292(11) 0.0199(10) 0.0218(10) -0.0072(8) -0.0010(8) 0.0012(8)
C9 0.050(2) 0.071(3) 0.045(2) -0.038(2) 0.0099(18) -0.0252(19)
C10 0.050(2) 0.081(4) 0.057(3) -0.046(3) -0.001(2) -0.011(2)
C11 0.0259(16) 0.0248(15) 0.0267(14) -0.0033(11) -0.0015(12) -0.0021(13)
C12 0.0489(15) 0.0223(12) 0.0257(11) -0.0084(9) -0.0119(10) 0.0072(10)
C13 0.0331(14) 0.0548(18) 0.0560(18) -0.0304(15) -0.0135(13) 0.0026(12)
C14 0.0333(14) 0.0525(18) 0.0476(16) -0.0289(14) -0.0009(12) 0.0008(12)
C15 0.0416(14) 0.0222(11) 0.0252(11) -0.0018(9) -0.0107(10) -0.0003(10)
C16 0.0334(14) 0.0406(16) 0.074(2) -0.0221(15) -0.0150(14) 0.0011(12)
C17 0.0320(14) 0.0463(17) 0.066(2) -0.0233(15) -0.0030(13) 0.0079(12)
C18 0.0667(19) 0.0277(13) 0.0375(14) -0.0069(11) -0.0241(14) 0.0011(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
S1 C3 1.760(2) . ?
S1 C1 1.819(3) . ?
S2 C4 1.752(2) . ?
S2 C2 1.809(3) . ?
S3 C5 1.765(2) . ?
S3 C3 1.766(2) . ?
S4 C5 1.746(2) . ?
S4 C4 1.775(2) . ?
S5 C7 1.752(2) . ?
S5 C6 1.774(3) . ?
S6 C6 1.742(2) . ?
S6 C8 1.764(2) . ?
S7 C7 1.753(2) . ?
S7 C9 1.822(3) . ?
S8 C8 1.742(3) . ?
S8 C10 1.811(4) . ?
S9 O3 1.425(2) . ?
S9 O2 1.431(3) . ?
S9 O1 1.5825(19) . ?
S9 C12 1.746(2) . ?
O1 C11 1.460(3) . ?
C1 C11 1.513(4) . ?
C1 C2 1.529(4) . ?
C3 C4 1.334(3) . ?
C5 C6 1.351(3) . ?
C7 C8 1.338(3) . ?
C9 C10 1.399(5) . ?
C12 C17 1.362(4) . ?
C12 C13 1.382(4) . ?
C13 C14 1.393(4) . ?
C14 C15 1.375(4) . ?
C15 C16 1.376(4) . ?
C15 C18 1.499(3) . ?
C16 C17 1.376(4) . ?
S1A C1A 1.793(16) . ?
S2A C2A 1.818(17) . ?
S7A C9A 1.809(9) . ?
S8A C10A 1.784(9) . ?
S9A O2A 1.420(17) . ?
S9A O3A 1.503(16) . ?
S9A O1A 1.582(8) . ?
O1A C11A 1.461(10) . ?
C1A C2A 1.53(2) . ?
C2A C11A 1.50(3) . ?
C9A C10A 1.442(16) . ?

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
C3 S1 C1 101.24(11) . . ?
C4 S2 C2 99.71(12) . . ?
C5 S3 C3 94.13(11) . . ?
C5 S4 C4 94.02(11) . . ?
C7 S5 C6 92.99(11) . . ?
C6 S6 C8 93.93(12) . . ?
C7 S7 C9 97.72(16) . . ?
C8 S8 C10 99.3(2) . . ?
O3 S9 O2 119.31(14) . . ?
O3 S9 O1 103.81(12) . . ?
O2 S9 O1 109.72(12) . . ?
O3 S9 C12 112.02(14) . . ?
O2 S9 C12 107.74(13) . . ?
O1 S9 C12 102.96(11) . . ?
C11 O1 S9 115.04(19) . . ?
C11 C1 C2 109.7(2) . . ?
C11 C1 S1 113.36(19) . . ?
C2 C1 S1 112.03(18) . . ?
C1 C2 S2 112.97(18) . . ?
C4 C3 S1 128.76(18) . . ?
C4 C3 S3 116.96(17) . . ?
S1 C3 S3 114.21(13) . . ?
C3 C4 S2 128.90(18) . . ?
C3 C4 S4 117.12(17) . . ?
S2 C4 S4 113.64(13) . . ?
C6 C5 S4 124.06(18) . . ?
C6 C5 S3 121.83(19) . . ?
S4 C5 S3 113.97(13) . . ?
C5 C6 S6 124.24(19) . . ?
C5 C6 S5 122.50(18) . . ?
S6 C6 S5 113.19(13) . . ?
C8 C7 S5 118.07(19) . . ?
C8 C7 S7 123.89(19) . . ?
S5 C7 S7 118.03(14) . . ?
C7 C8 S8 124.99(19) . . ?
C7 C8 S6 115.92(18) . . ?
S8 C8 S6 119.03(14) . . ?
C10 C9 S7 121.3(3) . . ?
C9 C10 S8 122.1(3) . . ?
O1 C11 C1 108.9(3) . . ?
C17 C12 C13 121.0(2) . . ?
C17 C12 S9 117.9(2) . . ?
C13 C12 S9 121.2(2) . . ?
C12 C13 C14 118.8(3) . . ?
C15 C14 C13 121.0(3) . . ?
C16 C15 C14 118.1(2) . . ?
C16 C15 C18 121.7(2) . . ?
C14 C15 C18 120.3(2) . . ?
C15 C16 C17 122.1(3) . . ?
C12 C17 C16 119.0(3) . . ?
O2A S9A O3A 120.4(9) . . ?
O2A S9A O1A 106.7(8) . . ?
O3A S9A O1A 109.0(8) . . ?
C11A O1A S9A 119.4(13) . . ?
C2A C1A S1A 112.3(11) . . ?
C1A C2A C11A 109.8(14) . . ?
C1A C2A S2A 114.3(11) . . ?
C11A C2A S2A 110.9(13) . . ?
C10A C9A S7A 123.6(12) . . ?
C9A C10A S8A 123.6(13) . . ?
O1A C11A C2A 111.7(16) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.081