# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2004

data_global

_journal_coden_Cambridge         177

_publ_contact_author_name        'Dr Simon Woodward'
_publ_contact_author_address     
;
Chemistry
University of Nottingham
School of Chemistry
University Park
Nottingham
NG7 2RD
UNITED KINGDOM
;
_publ_contact_author_email       simon.woodward@nottingham.ac.uk

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
On the Use of Mixtures of Organotin Species for Catalytic
Enantioselective Ketone Allylation - A Detective Story.
;

loop_
_publ_author_name
'Anthony Cunningham'
'Vijaya Mokal-Parekh'
'Claire Wilson'
'Simon Woodward'

data_snetcl
_database_code_depnum_ccdc_archive 'CCDC 222923'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H40 Cl4 O2 Sn4'
_chemical_formula_weight         929.08

_refine_special_details          
;
Disorder present in one CH2CH3 and both CH2CHCH2 chains.
C2, C7 and C10 modelled over 2 sites with occupancies 0.75 and 0.25.
Suitable distance restraints were applied and disordered hydrogens
placed on C1, C3, C6, C7 and C9 appropriate to each of these components.
Partially occupied atoms were refined with isotropic adps.
;

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.525(3)
_cell_length_b                   10.4917(15)
_cell_length_c                   15.695(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.085(2)
_cell_angle_gamma                90.00
_cell_volume                     3038.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2318
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      26.7

_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    2.031
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_absorpt_coefficient_mu    3.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_process_details   'Bruker SADABS v2.03 (2002)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            7619
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         27.51
_reflns_number_total             3464
_reflns_number_gt                2780
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2002)'
_computing_data_reduction        
'Bruker SAINT; Bruker SHELXTL v6.12 (Bruker, 20'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97; PLATON (Spek, 2002)'

_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^)+(0.0526P)^2^] 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_number_reflns         3464
_refine_ls_number_parameters     123
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.054
_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
Sn1 Sn 0.306888(15) 0.82413(3) 0.071334(18) 0.02826(11) Uani 1 1 d . . .
Cl1 Cl 0.25167(6) 1.01837(12) 0.15315(8) 0.0438(3) Uani 1 1 d . . .
Sn2 Sn 0.127741(17) 0.95898(3) 0.05087(2) 0.03772(12) Uani 1 1 d . B .
Cl2 Cl 0.03954(7) 0.85297(14) -0.05340(9) 0.0540(4) Uani 1 1 d . . .
C1 C 0.3200(3) 0.7162(5) 0.1875(3) 0.0389(11) Uani 1 1 d D . .
H1A H 0.2757 0.7246 0.2178 0.047 Uiso 0.75 1 calc PR A 1
H1B H 0.3259 0.6250 0.1733 0.047 Uiso 0.75 1 calc PR A 1
H1C H 0.2748 0.6692 0.1956 0.047 Uiso 0.25 1 calc PR A 2
H1D H 0.3596 0.6533 0.1844 0.047 Uiso 0.25 1 calc PR A 2
O1 O 0.20130(15) 0.8283(3) 0.01852(19) 0.0305(7) Uani 1 1 d . . .
C2 C 0.3831(4) 0.7579(7) 0.2447(5) 0.058(2) Uani 0.75 1 d PD B 1
H2A H 0.4284 0.7328 0.2261 0.069 Uiso 0.75 1 calc PR B 1
C2' C 0.3365(9) 0.7990(18) 0.2563(10) 0.040(4) Uiso 0.25 1 d PD B 2
H2'A H 0.2977 0.8562 0.2630 0.047 Uiso 0.25 1 calc PR B 2
C3 C 0.3882(6) 0.8187(10) 0.3115(6) 0.126(4) Uiso 1 1 d D . .
H3A H 0.3458 0.8480 0.3352 0.151 Uiso 0.75 1 calc PR B 1
H3B H 0.4347 0.8365 0.3397 0.151 Uiso 0.75 1 calc PR B 1
H3C H 0.4308 0.7681 0.3122 0.151 Uiso 0.25 1 calc PR B 2
H3D H 0.3849 0.8843 0.3527 0.151 Uiso 0.25 1 calc PR B 2
C4 C 0.3760(3) 0.9483(5) 0.0101(3) 0.0401(11) Uani 1 1 d D . .
H4A H 0.4058 0.8971 -0.0265 0.048 Uiso 1 1 calc R B .
H4B H 0.3457 1.0065 -0.0278 0.048 Uiso 1 1 calc R . .
C5 C 0.4261(3) 1.0278(5) 0.0707(4) 0.0545(15) Uani 1 1 d D B .
H5A H 0.4561 1.0825 0.0376 0.082 Uiso 1 1 calc R . .
H5B H 0.4573 0.9712 0.1075 0.082 Uiso 1 1 calc R . .
H5C H 0.3971 1.0809 0.1062 0.082 Uiso 1 1 calc R . .
C6 C 0.0796(3) 0.9081(5) 0.1643(4) 0.0499(13) Uani 1 1 d D . .
H6A H 0.0841 0.9806 0.2048 0.060 Uiso 0.75 1 calc PR B 1
H6B H 0.0273 0.8917 0.1498 0.060 Uiso 0.75 1 calc PR B 1
H6C H 0.1140 0.9267 0.2147 0.060 Uiso 0.25 1 calc PR B 2
H6D H 0.0356 0.9603 0.1689 0.060 Uiso 0.25 1 calc PR B 2
C7 C 0.1125(4) 0.7962(8) 0.2057(5) 0.062(2) Uiso 0.75 1 d PD B 1
H7A H 0.1577 0.8109 0.2377 0.074 Uiso 0.75 1 calc PR B 1
C7' C 0.0607(12) 0.7775(13) 0.1644(15) 0.071(7) Uiso 0.25 1 d PD B 2
H7'A H 0.0188 0.7559 0.1279 0.086 Uiso 0.25 1 calc PR B 2
C8 C 0.0909(5) 0.6838(8) 0.2058(5) 0.096(3) Uiso 1 1 d D . .
H8A H 0.0461 0.6614 0.1752 0.115 Uiso 0.75 1 calc PR B 1
H8B H 0.1191 0.6204 0.2365 0.115 Uiso 0.75 1 calc PR B 1
H8C H 0.1331 0.6975 0.2437 0.115 Uiso 0.25 1 calc PR B 2
H8D H 0.0711 0.6005 0.1986 0.115 Uiso 0.25 1 calc PR B 2
C9 C 0.1390(3) 1.1321(6) -0.0167(4) 0.0542(14) Uiso 1 1 d D . .
H9A H 0.0934 1.1485 -0.0529 0.065 Uiso 0.75 1 calc PR B 1
H9B H 0.1456 1.2025 0.0253 0.065 Uiso 0.75 1 calc PR B 1
H9C H 0.0910 1.1743 -0.0237 0.065 Uiso 0.25 1 calc PR B 2
H9D H 0.1719 1.1886 0.0192 0.065 Uiso 0.25 1 calc PR B 2
C10 C 0.2027(4) 1.1350(8) -0.0743(5) 0.055(2) Uiso 0.75 1 d PD B 1
H10A H 0.2037 1.2176 -0.1032 0.083 Uiso 0.75 1 calc PR B 1
H10B H 0.1963 1.0669 -0.1170 0.083 Uiso 0.75 1 calc PR B 1
H10C H 0.2485 1.1222 -0.0389 0.083 Uiso 0.75 1 calc PR B 1
C10' C 0.1666(13) 1.123(2) -0.1014(11) 0.050(5) Uiso 0.25 1 d PD B 2
H10D H 0.1688 1.2079 -0.1265 0.075 Uiso 0.25 1 calc PR B 2
H10E H 0.1341 1.0687 -0.1385 0.075 Uiso 0.25 1 calc PR B 2
H10F H 0.2152 1.0851 -0.0956 0.075 Uiso 0.25 1 calc PR B 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
Sn1 0.02452(16) 0.02966(18) 0.03036(17) 0.00041(12) 0.00116(12) -0.00132(11)
Cl1 0.0385(6) 0.0401(7) 0.0536(7) -0.0166(6) 0.0086(5) -0.0020(5)
Sn2 0.03063(18) 0.0344(2) 0.0492(2) -0.00202(15) 0.00965(15) 0.00731(13)
Cl2 0.0321(6) 0.0628(9) 0.0656(9) -0.0122(7) -0.0038(6) 0.0110(6)
C1 0.047(3) 0.032(3) 0.038(3) 0.007(2) 0.006(2) -0.002(2)
O1 0.0212(14) 0.0301(17) 0.0398(17) -0.0037(13) 0.0004(12) 0.0053(12)
C2 0.068(5) 0.052(5) 0.051(4) 0.007(4) -0.006(4) -0.003(4)
C4 0.031(2) 0.044(3) 0.047(3) 0.004(2) 0.012(2) -0.001(2)
C5 0.045(3) 0.043(3) 0.077(4) -0.008(3) 0.017(3) -0.009(2)
C6 0.036(3) 0.060(4) 0.056(3) -0.008(3) 0.015(2) 0.003(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
Sn1 O1 2.056(3) . ?
Sn1 C4 2.116(5) . ?
Sn1 O1 2.129(3) 7_565 ?
Sn1 C1 2.141(4) . ?
Sn1 Cl1 2.6609(12) . ?
Cl1 Sn2 2.7537(13) . ?
Sn2 O1 2.029(3) . ?
Sn2 C9 2.123(6) . ?
Sn2 C6 2.129(5) . ?
Sn2 Cl2 2.4720(14) . ?
C1 C2' 1.399(13) . ?
C1 C2 1.475(8) . ?
O1 Sn1 2.129(3) 7_565 ?
C2 C3 1.224(8) . ?
C2' C3 1.250(9) . ?
C4 C5 1.519(7) . ?
C6 C7' 1.414(15) . ?
C6 C7 1.450(9) . ?
C7 C8 1.246(8) . ?
C7' C8 1.279(10) . ?
C9 C10' 1.468(14) . ?
C9 C10 1.548(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sn1 C4 113.31(16) . . ?
O1 Sn1 O1 74.90(12) . 7_565 ?
C4 Sn1 O1 99.91(16) . 7_565 ?
O1 Sn1 C1 112.74(16) . . ?
C4 Sn1 C1 133.22(19) . . ?
O1 Sn1 C1 99.36(15) 7_565 . ?
O1 Sn1 Cl1 77.62(8) . . ?
C4 Sn1 Cl1 91.23(14) . . ?
O1 Sn1 Cl1 152.52(8) 7_565 . ?
C1 Sn1 Cl1 90.79(14) . . ?
Sn1 Cl1 Sn2 83.21(4) . . ?
O1 Sn2 C9 110.80(18) . . ?
O1 Sn2 C6 112.36(17) . . ?
C9 Sn2 C6 134.4(2) . . ?
O1 Sn2 Cl2 87.10(9) . . ?
C9 Sn2 Cl2 98.21(16) . . ?
C6 Sn2 Cl2 98.01(16) . . ?
O1 Sn2 Cl1 75.82(9) . . ?
C9 Sn2 Cl1 89.07(16) . . ?
C6 Sn2 Cl1 87.65(15) . . ?
Cl2 Sn2 Cl1 162.89(4) . . ?
C2' C1 Sn1 109.2(8) . . ?
C2 C1 Sn1 112.7(4) . . ?
Sn2 O1 Sn1 123.33(15) . . ?
Sn2 O1 Sn1 131.56(14) . 7_565 ?
Sn1 O1 Sn1 105.10(12) . 7_565 ?
C3 C2 C1 132.4(8) . . ?
C3 C2' C1 137.7(16) . . ?
C5 C4 Sn1 114.4(4) . . ?
C7' C6 Sn2 111.5(11) . . ?
C7 C6 Sn2 112.7(4) . . ?
C8 C7 C6 130.1(8) . . ?
C8 C7' C6 130.4(16) . . ?
C10' C9 Sn2 116.9(10) . . ?
C10 C9 Sn2 114.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.043
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.135