# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Ari Koskinen'
'Kaisa Karisalmi'
'Kari Rissanen'

_publ_contact_author_name        'Prof Ari Koskinen'
_publ_contact_author_address     
;
Laboratory of Organic Chemistry
Helsinki University of Technology
Kemistintie 1
PO Box 6100
Espoo
FIN-02015
FINLAND
;

_publ_contact_author_email       ARI.KOSKINEN@HUT.FI

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
An enantioselective synthesis of the C(33)-C(37)
fragment of Amphotericin B
;

data_7b
_database_code_CSD               215705

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H24 O7 S'
_chemical_formula_weight         360.41

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   P21

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

_cell_length_a                   5.2341(2)
_cell_length_b                   12.3751(5)
_cell_length_c                   14.2381(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.6880(10)
_cell_angle_gamma                90.00
_cell_volume                     913.95(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.210
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5702
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.04
_reflns_number_total             3175
_reflns_number_gt                2627
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0500P)^2^+0.3556P] 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     SHELXL
_refine_ls_extinction_coef       0.022(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   -0.02(11)
_refine_ls_number_reflns         3175
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.6540(2) -0.16156(8) 0.80521(7) 0.0588(3) Uani 1 1 d . . .
O14 O -0.1440(4) 0.39481(17) 0.72390(15) 0.0327(5) Uani 1 1 d . . .
O8 O 0.1122(4) 0.13453(16) 0.79088(15) 0.0304(5) Uani 1 1 d . . .
O13 O -0.0780(4) 0.31860(18) 0.86906(15) 0.0363(5) Uani 1 1 d . . .
O11 O 0.4865(3) 0.18835(18) 0.74637(15) 0.0325(5) Uani 1 1 d . . .
O20 O 0.1871(4) 0.34072(19) 0.55357(14) 0.0340(5) Uani 1 1 d . . .
O19 O 0.3884(5) 0.1799(2) 0.55330(17) 0.0516(7) Uani 1 1 d . . .
O4 O 0.3131(6) 0.0541(2) 0.9959(2) 0.0656(9) Uani 1 1 d . . .
C9 C 0.0444(5) 0.2249(2) 0.7324(2) 0.0259(7) Uani 1 1 d . . .
H9 H -0.0776 0.2035 0.6772 0.031 Uiso 1 1 calc R . .
C12 C -0.0682(5) 0.3159(2) 0.7855(2) 0.0264(7) Uani 1 1 d . . .
C18 C 0.3024(5) 0.2535(2) 0.5944(2) 0.0272(7) Uani 1 1 d . . .
C10 C 0.3050(5) 0.2614(2) 0.7002(2) 0.0253(6) Uani 1 1 d . . .
H10 H 0.3467 0.3353 0.7218 0.030 Uiso 1 1 calc R . .
C7 C 0.3777(5) 0.1475(3) 0.8254(2) 0.0312(7) Uani 1 1 d . . .
H7 H 0.3997 0.1997 0.8776 0.037 Uiso 1 1 calc R . .
C21 C 0.1355(5) 0.3441(3) 0.4502(2) 0.0338(7) Uani 1 1 d . . .
H21 H 0.2792 0.3111 0.4231 0.041 Uiso 1 1 calc R . .
C3 C 0.5109(6) 0.0424(3) 0.8556(2) 0.0353(8) Uani 1 1 d . . .
H3 H 0.6969 0.0564 0.8646 0.042 Uiso 1 1 calc R . .
C15 C -0.2257(6) 0.4984(3) 0.7605(2) 0.0332(8) Uani 1 1 d . . .
H15 H -0.3400 0.4853 0.8084 0.040 Uiso 1 1 calc R . .
C4 C 0.4412(7) 0.0023(3) 0.9487(2) 0.0415(8) Uani 1 1 d . . .
C16 C 0.0070(7) 0.5611(3) 0.8039(3) 0.0472(9) Uani 1 1 d . . .
H16A H 0.1004 0.5195 0.8541 0.071 Uiso 1 1 calc R . .
H16B H -0.0473 0.6280 0.8289 0.071 Uiso 1 1 calc R . .
H16C H 0.1164 0.5757 0.7564 0.071 Uiso 1 1 calc R . .
C6 C 0.5227(10) -0.1952(3) 0.9125(3) 0.0647(12) Uani 1 1 d . . .
H6A H 0.3408 -0.2116 0.8969 0.078 Uiso 1 1 calc R . .
H6B H 0.6082 -0.2594 0.9403 0.078 Uiso 1 1 calc R . .
C23 C 0.1195(8) 0.4636(3) 0.4260(3) 0.0522(10) Uani 1 1 d . . .
H23A H -0.0219 0.4956 0.4525 0.078 Uiso 1 1 calc R . .
H23B H 0.0930 0.4723 0.3584 0.078 Uiso 1 1 calc R . .
H23C H 0.2772 0.4985 0.4516 0.078 Uiso 1 1 calc R . .
C22 C -0.1071(7) 0.2838(3) 0.4181(3) 0.0530(10) Uani 1 1 d . . .
H22A H -0.0868 0.2096 0.4374 0.080 Uiso 1 1 calc R . .
H22B H -0.1439 0.2874 0.3503 0.080 Uiso 1 1 calc R . .
H22C H -0.2468 0.3155 0.4459 0.080 Uiso 1 1 calc R . .
C2 C 0.4587(8) -0.0428(3) 0.7782(3) 0.0502(10) Uani 1 1 d . . .
H2A H 0.4945 -0.0126 0.7185 0.060 Uiso 1 1 calc R . .
H2B H 0.2780 -0.0629 0.7712 0.060 Uiso 1 1 calc R . .
C5 C 0.5545(10) -0.1055(3) 0.9835(3) 0.0600(12) Uani 1 1 d . . .
H5A H 0.7372 -0.0957 1.0043 0.072 Uiso 1 1 calc R . .
H5B H 0.4750 -0.1274 1.0382 0.072 Uiso 1 1 calc R . .
C17 C -0.3736(7) 0.5537(3) 0.6760(3) 0.0454(9) Uani 1 1 d . . .
H17A H -0.2627 0.5644 0.6283 0.068 Uiso 1 1 calc R . .
H17B H -0.4349 0.6224 0.6950 0.068 Uiso 1 1 calc R . .
H17C H -0.5175 0.5096 0.6509 0.068 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 0.0895(7) 0.0414(6) 0.0460(6) -0.0002(5) 0.0111(5) 0.0322(6)
O14 0.0404(12) 0.0237(11) 0.0357(13) 0.0031(10) 0.0114(10) 0.0079(9)
O8 0.0320(11) 0.0190(11) 0.0417(14) 0.0044(9) 0.0102(9) 0.0027(9)
O13 0.0449(12) 0.0349(14) 0.0292(13) 0.0000(10) 0.0050(9) 0.0070(10)
O11 0.0227(10) 0.0393(13) 0.0356(13) 0.0137(10) 0.0046(9) 0.0081(9)
O20 0.0380(11) 0.0352(12) 0.0289(11) 0.0067(11) 0.0044(9) 0.0087(10)
O19 0.0696(16) 0.0483(16) 0.0388(15) 0.0038(12) 0.0142(12) 0.0291(13)
O4 0.113(2) 0.0460(16) 0.0452(17) 0.0066(14) 0.0364(16) 0.0272(17)
C9 0.0243(14) 0.0225(16) 0.0315(17) 0.0014(13) 0.0062(12) 0.0014(11)
C12 0.0235(14) 0.0219(17) 0.0337(19) 0.0012(13) 0.0039(12) -0.0005(11)
C18 0.0225(14) 0.0289(17) 0.0303(17) 0.0033(14) 0.0044(12) -0.0007(13)
C10 0.0224(14) 0.0206(15) 0.0323(17) 0.0031(13) 0.0020(11) -0.0001(11)
C7 0.0299(15) 0.0338(18) 0.0298(17) 0.0045(14) 0.0041(12) 0.0068(13)
C21 0.0298(15) 0.0424(19) 0.0287(16) 0.0048(16) 0.0024(12) 0.0023(15)
C3 0.0441(18) 0.0286(18) 0.0330(19) 0.0035(15) 0.0047(14) 0.0087(14)
C15 0.0345(16) 0.0239(17) 0.044(2) -0.0011(14) 0.0142(14) 0.0064(13)
C4 0.057(2) 0.038(2) 0.029(2) 0.0010(16) 0.0057(16) 0.0111(17)
C16 0.045(2) 0.0298(19) 0.065(3) -0.0058(18) 0.0021(17) 0.0034(15)
C6 0.097(3) 0.028(2) 0.073(3) 0.015(2) 0.023(3) 0.011(2)
C23 0.060(2) 0.048(2) 0.047(2) 0.0152(19) -0.0018(18) -0.0072(18)
C22 0.047(2) 0.053(2) 0.055(2) 0.0132(19) -0.0090(17) -0.0099(18)
C2 0.067(2) 0.044(2) 0.037(2) -0.0028(17) -0.0030(18) 0.0139(18)
C5 0.095(3) 0.044(2) 0.045(2) 0.011(2) 0.021(2) 0.019(2)
C17 0.048(2) 0.0286(19) 0.060(2) 0.0089(17) 0.0085(17) 0.0050(15)

_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 C2 1.802(4) . ?
S1 C6 1.805(5) . ?
O14 C12 1.337(4) . ?
O14 C15 1.469(4) . ?
O8 C9 1.411(3) . ?
O8 C7 1.419(4) . ?
O13 C12 1.198(4) . ?
O11 C10 1.408(3) . ?
O11 C7 1.420(4) . ?
O20 C18 1.331(4) . ?
O20 C21 1.460(4) . ?
O19 C18 1.202(4) . ?
O4 C4 1.197(4) . ?
C9 C12 1.519(4) . ?
C9 C10 1.562(4) . ?
C18 C10 1.509(4) . ?
C7 C3 1.511(4) . ?
C21 C22 1.491(5) . ?
C21 C23 1.519(5) . ?
C3 C4 1.505(5) . ?
C3 C2 1.523(5) . ?
C15 C17 1.504(5) . ?
C15 C16 1.505(5) . ?
C4 C5 1.517(5) . ?
C6 C5 1.495(6) . ?

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
C2 S1 C6 95.7(2) . . ?
C12 O14 C15 118.7(2) . . ?
C9 O8 C7 105.8(2) . . ?
C10 O11 C7 106.3(2) . . ?
C18 O20 C21 118.3(2) . . ?
O8 C9 C12 112.2(2) . . ?
O8 C9 C10 104.0(2) . . ?
C12 C9 C10 110.1(2) . . ?
O13 C12 O14 125.7(3) . . ?
O13 C12 C9 125.9(3) . . ?
O14 C12 C9 108.4(2) . . ?
O19 C18 O20 125.4(3) . . ?
O19 C18 C10 125.5(3) . . ?
O20 C18 C10 109.1(2) . . ?
O11 C10 C18 109.9(2) . . ?
O11 C10 C9 103.8(2) . . ?
C18 C10 C9 112.5(2) . . ?
O8 C7 O11 104.1(2) . . ?
O8 C7 C3 113.2(3) . . ?
O11 C7 C3 108.3(2) . . ?
O20 C21 C22 109.3(3) . . ?
O20 C21 C23 104.7(3) . . ?
C22 C21 C23 113.5(3) . . ?
C4 C3 C7 112.2(3) . . ?
C4 C3 C2 111.6(3) . . ?
C7 C3 C2 111.0(3) . . ?
O14 C15 C17 104.9(3) . . ?
O14 C15 C16 109.7(2) . . ?
C17 C15 C16 113.3(3) . . ?
O4 C4 C3 122.6(3) . . ?
O4 C4 C5 120.8(3) . . ?
C3 C4 C5 116.5(3) . . ?
C5 C6 S1 112.4(3) . . ?
C3 C2 S1 111.6(2) . . ?
C6 C5 C4 115.4(3) . . ?

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 O8 C9 C12 -94.4(3) . . . . ?
C7 O8 C9 C10 24.5(3) . . . . ?
C15 O14 C12 O13 5.8(4) . . . . ?
C15 O14 C12 C9 -171.4(2) . . . . ?
O8 C9 C12 O13 7.2(4) . . . . ?
C10 C9 C12 O13 -108.1(3) . . . . ?
O8 C9 C12 O14 -175.6(2) . . . . ?
C10 C9 C12 O14 69.1(3) . . . . ?
C21 O20 C18 O19 6.6(4) . . . . ?
C21 O20 C18 C10 -172.8(2) . . . . ?
C7 O11 C10 C18 -143.1(2) . . . . ?
C7 O11 C10 C9 -22.6(3) . . . . ?
O19 C18 C10 O11 17.5(4) . . . . ?
O20 C18 C10 O11 -163.1(2) . . . . ?
O19 C18 C10 C9 -97.6(3) . . . . ?
O20 C18 C10 C9 81.8(3) . . . . ?
O8 C9 C10 O11 -1.2(3) . . . . ?
C12 C9 C10 O11 119.1(3) . . . . ?
O8 C9 C10 C18 117.5(2) . . . . ?
C12 C9 C10 C18 -122.2(3) . . . . ?
C9 O8 C7 O11 -39.5(3) . . . . ?
C9 O8 C7 C3 -156.9(2) . . . . ?
C10 O11 C7 O8 38.8(3) . . . . ?
C10 O11 C7 C3 159.6(2) . . . . ?
C18 O20 C21 C22 82.3(3) . . . . ?
C18 O20 C21 C23 -155.8(3) . . . . ?
O8 C7 C3 C4 -74.8(4) . . . . ?
O11 C7 C3 C4 170.3(3) . . . . ?
O8 C7 C3 C2 50.8(4) . . . . ?
O11 C7 C3 C2 -64.1(3) . . . . ?
C12 O14 C15 C17 -162.6(2) . . . . ?
C12 O14 C15 C16 75.4(3) . . . . ?
C7 C3 C4 O4 -6.2(5) . . . . ?
C2 C3 C4 O4 -131.5(4) . . . . ?
C7 C3 C4 C5 177.2(3) . . . . ?
C2 C3 C4 C5 51.9(4) . . . . ?
C2 S1 C6 C5 -57.8(4) . . . . ?
C4 C3 C2 S1 -62.9(4) . . . . ?
C7 C3 C2 S1 171.2(2) . . . . ?
C6 S1 C2 C3 61.8(3) . . . . ?
S1 C6 C5 C4 56.1(5) . . . . ?
O4 C4 C5 C6 133.8(4) . . . . ?
C3 C4 C5 C6 -49.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.047