# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2007

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182

_publ_section_title              
;Application of Furyl-Stabilized Sulfur Ylides to a
Concise Synthesis of 8a-epi-Swainsonine
;
_publ_contact_author_name        'Prof. Varinder Aggarwal'
_publ_contact_author_email       V.AGGARWAL@BRISTOL.AC.UK
loop_
_publ_author_name
V.Aggarwal
'Jie Bi'

# Attachment '8a-epi-swainsonine.cif'

data_8a-epi-swainsonine
_database_code_depnum_ccdc_archive 'CCDC 659348'

_audit_creation_method           SHELXL-97
_chemical_formula_moiety         'C8 H16 N O3, Cl'
_chemical_formula_sum            'C8 H16 Cl N O3'
_chemical_formula_weight         209.67
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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                   8.3941(3)
_cell_length_b                   9.4475(3)
_cell_length_c                   12.0154(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     952.86(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5210
_cell_measurement_theta_min      5.96
_cell_measurement_theta_max      70.17

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    3.381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.602
_diffrn_detector_type            'Bruker-AXS SMART 6000'
_diffrn_measurement_details      'frames, 0.3\% width'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS D8'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'glass fibre'
_diffrn_radiation_collimation    'Osmic CMF12-38Cu6 (blue) mirror optics'
_diffrn_radiation_monochromator  'Osmic CMF12-38Cu6 (blue) mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   rotating-anode
_diffrn_source_current           120
_diffrn_source_power             4.8
_diffrn_source_size              '3 x 0.3mm'
_diffrn_source_target            Cu
_diffrn_source_type              'MAC Science M18XCE'
_diffrn_source_voltage           40
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7381
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.96
_diffrn_reflns_theta_max         69.95
_reflns_number_total             1766
_reflns_number_gt                1718
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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^)+(0.0429P)^2^+0.6223P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.038(19)
_refine_ls_number_reflns         1766
_refine_ls_number_parameters     121
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0823
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
C1 C 0.7732(3) 0.1152(2) 0.65736(19) 0.0184(5) Uani 1 1 d . . .
H1A H 0.6879 0.0467 0.6391 0.022 Uiso 1 1 calc R . .
H1B H 0.8717 0.0615 0.6739 0.022 Uiso 1 1 calc R . .
C2 C 0.8015(3) 0.2136(2) 0.55883(19) 0.0193(5) Uani 1 1 d . . .
H2A H 0.6985 0.2549 0.5351 0.023 Uiso 1 1 calc R . .
H2B H 0.8444 0.1580 0.4958 0.023 Uiso 1 1 calc R . .
C3 C 0.9174(3) 0.3332(2) 0.58673(19) 0.0182(5) Uani 1 1 d . . .
H3A H 1.0240 0.2932 0.6026 0.022 Uiso 1 1 calc R . .
H3B H 0.9272 0.3976 0.5221 0.022 Uiso 1 1 calc R . .
C4 C 0.8584(3) 0.4158(2) 0.68767(17) 0.0139(4) Uani 1 1 d . . .
H4 H 0.9351 0.4933 0.7061 0.017 Uiso 1 1 calc R . .
C5 C 0.8443(3) 0.3138(2) 0.78539(17) 0.0124(4) Uani 1 1 d . . .
H5 H 0.9503 0.2679 0.7973 0.015 Uiso 1 1 calc R . .
C6 C 0.7813(3) 0.3631(2) 0.89743(18) 0.0140(4) Uani 1 1 d . . .
H6 H 0.6795 0.4163 0.8867 0.017 Uiso 1 1 calc R . .
C7 C 0.7470(2) 0.2206(2) 0.95747(18) 0.0149(5) Uani 1 1 d . . .
H7 H 0.6573 0.2315 1.0115 0.018 Uiso 1 1 calc R . .
C8 C 0.7006(3) 0.1192(2) 0.86340(18) 0.0162(5) Uani 1 1 d . . .
H8A H 0.7685 0.0335 0.8648 0.019 Uiso 1 1 calc R . .
H8B H 0.5878 0.0900 0.8707 0.019 Uiso 1 1 calc R . .
N1 N 0.7258(2) 0.20093(17) 0.75667(15) 0.0129(4) Uani 1 1 d D . .
H1 H 0.637(2) 0.239(2) 0.7372(19) 0.015 Uiso 1 1 d D . .
O1 O 0.70617(18) 0.47435(16) 0.66189(13) 0.0156(3) Uani 1 1 d . . .
H1C H 0.6916 0.5479 0.6999 0.023 Uiso 1 1 calc R . .
O2 O 0.89454(18) 0.45121(16) 0.94844(12) 0.0165(3) Uani 1 1 d . . .
H2 H 0.8610 0.4764 1.0113 0.025 Uiso 1 1 calc R . .
O3 O 0.88238(10) 0.16789(15) 1.01079(4) 0.0190(4) Uani 1 1 d . . .
H3 H 0.8660 0.1643 1.0797 0.029 Uiso 1 1 calc R . .
Cl Cl 0.85761(6) 0.23966(5) 1.26299(4) 0.01773(15) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0232(12) 0.0151(11) 0.0167(12) -0.0050(9) -0.0021(10) 0.0010(9)
C2 0.0249(11) 0.0183(12) 0.0147(11) -0.0029(9) -0.0024(9) 0.0035(9)
C3 0.0182(11) 0.0222(11) 0.0141(11) 0.0007(9) 0.0013(9) 0.0024(10)
C4 0.0122(9) 0.0153(9) 0.0142(10) 0.0013(8) -0.0009(9) -0.0019(9)
C5 0.0127(9) 0.0130(9) 0.0115(10) -0.0017(8) -0.0027(8) 0.0005(8)
C6 0.0139(10) 0.0159(10) 0.0124(11) 0.0006(9) -0.0012(9) 0.0010(9)
C7 0.0132(10) 0.0186(12) 0.0129(10) 0.0022(9) 0.0001(8) -0.0011(8)
C8 0.0180(10) 0.0148(10) 0.0157(11) 0.0030(9) -0.0007(9) -0.0006(9)
N1 0.0128(9) 0.0123(8) 0.0136(9) 0.0007(7) -0.0022(7) 0.0007(7)
O1 0.0163(7) 0.0148(7) 0.0156(8) -0.0006(6) -0.0027(6) 0.0016(6)
O2 0.0178(8) 0.0181(8) 0.0135(8) -0.0051(6) 0.0005(6) -0.0041(6)
O3 0.0175(8) 0.0226(8) 0.0170(8) 0.0034(6) -0.0031(7) 0.0015(7)
Cl 0.0179(3) 0.0171(2) 0.0181(3) 0.00322(19) 0.00042(19) 0.0003(2)

_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
C1 N1 1.496(3) . ?
C1 C2 1.524(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.528(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.525(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O1 1.426(3) . ?
C4 C5 1.524(3) . ?
C4 H4 1.0000 . ?
C5 N1 1.498(3) . ?
C5 C6 1.520(3) . ?
C5 H5 1.0000 . ?
C6 O2 1.404(3) . ?
C6 C7 1.554(3) . ?
C6 H6 1.0000 . ?
C7 O3 1.396(2) . ?
C7 C8 1.532(3) . ?
C7 H7 1.0000 . ?
C8 N1 1.512(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
N1 H1 0.862(16) . ?
O1 H1C 0.8400 . ?
O2 H2 0.8400 . ?
O3 H3 0.8400 . ?

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
N1 C1 C2 109.33(18) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
C1 C2 C3 112.31(19) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 110.23(19) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
O1 C4 C5 110.08(17) . . ?
O1 C4 C3 108.47(17) . . ?
C5 C4 C3 108.29(17) . . ?
O1 C4 H4 110.0 . . ?
C5 C4 H4 110.0 . . ?
C3 C4 H4 110.0 . . ?
N1 C5 C6 101.02(17) . . ?
N1 C5 C4 108.92(17) . . ?
C6 C5 C4 121.03(17) . . ?
N1 C5 H5 108.4 . . ?
C6 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
O2 C6 C5 109.44(18) . . ?
O2 C6 C7 115.87(17) . . ?
C5 C6 C7 102.13(17) . . ?
O2 C6 H6 109.7 . . ?
C5 C6 H6 109.7 . . ?
C7 C6 H6 109.7 . . ?
O3 C7 C8 108.83(17) . . ?
O3 C7 C6 111.79(17) . . ?
C8 C7 C6 104.25(17) . . ?
O3 C7 H7 110.6 . . ?
C8 C7 H7 110.6 . . ?
C6 C7 H7 110.6 . . ?
N1 C8 C7 105.72(16) . . ?
N1 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
N1 C8 H8B 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C1 N1 C5 113.10(17) . . ?
C1 N1 C8 115.95(16) . . ?
C5 N1 C8 105.13(16) . . ?
C1 N1 H1 103.9(16) . . ?
C5 N1 H1 109.9(16) . . ?
C8 N1 H1 108.8(16) . . ?
C4 O1 H1C 109.5 . . ?
C6 O2 H2 109.5 . . ?
C7 O3 H3 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
N1 C1 C2 C3 52.5(3) . . . . ?
C1 C2 C3 C4 -55.8(3) . . . . ?
C2 C3 C4 O1 -60.3(2) . . . . ?
C2 C3 C4 C5 59.2(2) . . . . ?
O1 C4 C5 N1 57.3(2) . . . . ?
C3 C4 C5 N1 -61.1(2) . . . . ?
O1 C4 C5 C6 -58.9(3) . . . . ?
C3 C4 C5 C6 -177.38(19) . . . . ?
N1 C5 C6 O2 168.81(16) . . . . ?
C4 C5 C6 O2 -71.0(2) . . . . ?
N1 C5 C6 C7 45.51(19) . . . . ?
C4 C5 C6 C7 165.68(18) . . . . ?
O2 C6 C7 O3 -32.9(2) . . . . ?
C5 C6 C7 O3 85.96(19) . . . . ?
O2 C6 C7 C8 -150.28(19) . . . . ?
C5 C6 C7 C8 -31.4(2) . . . . ?
O3 C7 C8 N1 -113.96(18) . . . . ?
C6 C7 C8 N1 5.5(2) . . . . ?
C2 C1 N1 C5 -55.8(2) . . . . ?
C2 C1 N1 C8 -177.30(17) . . . . ?
C6 C5 N1 C1 -170.40(17) . . . . ?
C4 C5 N1 C1 61.1(2) . . . . ?
C6 C5 N1 C8 -42.95(19) . . . . ?
C4 C5 N1 C8 -171.40(17) . . . . ?
C7 C8 N1 C1 148.85(18) . . . . ?
C7 C8 N1 C5 23.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl 0.862(16) 2.352(18) 3.150(3) 154(2) 4_457
O1 H1C Cl 0.84 2.19 3.010(2) 167 2_664
O2 H2 O1 0.84 1.95 2.791(2) 176 2_665
O3 H3 Cl 0.84 2.32 3.1122(7) 158 .

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        69.95
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.064