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

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

loop_
_publ_author_name
'Adam Nelson'
'Stephen Bartlett'
'Robert Hodgson'
'Joanne M. Holland'
'Matthew Jones'
'Colin Kilner'
;
S.Warriner
;

_publ_contact_author_name        'Dr Adam Nelson'
_publ_contact_author_address     
;
Chemistry
University of Leeds
University of Leeds
Leeds
LS2 9JT
UNITED KINGDOM
;

_publ_contact_author_email       ADAMN@CHEM.LEEDS.AC.UK

_publ_section_title              
;
Exploiting predisposition in the stereoselective
synthesis of mono-, bi- and tetracyclic oxygen heterocycles:
Equilibration between, and trapping of, alternative di- and tetraacetals
;

data_jmh277
_database_code_CSD               206733

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H30 O8'
_chemical_formula_weight         374.42

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'

_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                   17.7588(10)
_cell_length_b                   7.8904(4)
_cell_length_c                   13.1044(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.161(3)
_cell_angle_gamma                90.00
_cell_volume                     1835.86(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.106
_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      150(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  'Nonius KappaCCD area-detector diffractometer'
_diffrn_measurement_method       'phi-omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7982
_diffrn_reflns_av_R_equivalents  0.1062
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1795
_reflns_number_gt                1413
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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^)+(0.0689P)^2^+1.1658P] 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       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1795
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
O50 O 0.19530(7) 0.14872(16) 0.77883(9) 0.0369(4) Uani 1 1 d . . .
O9 O 0.03543(7) 0.28536(15) 0.52660(9) 0.0326(4) Uani 1 1 d . . .
O80 O 0.15796(7) 0.34740(15) 0.47545(9) 0.0349(4) Uani 1 1 d . . .
O4 O 0.09292(7) 0.32349(16) 0.73500(9) 0.0346(4) Uani 1 1 d . . .
C8 C 0.11320(10) 0.2735(2) 0.55278(13) 0.0299(4) Uani 1 1 d . . .
C1 C 0.00914(10) 0.4553(2) 0.54987(13) 0.0313(4) Uani 1 1 d . . .
H1 H -0.0398(10) 0.443(2) 0.5917(14) 0.030(5) Uiso 1 1 d . . .
C5 C 0.11710(10) 0.1569(2) 0.75927(14) 0.0345(5) Uani 1 1 d . . .
H5 H 0.0907 0.1194 0.8220 0.041 Uiso 1 1 calc R . .
C2 C 0.07268(10) 0.5405(2) 0.61277(13) 0.0340(5) Uani 1 1 d . . .
H2A H 0.1000 0.6242 0.5711 0.041 Uiso 1 1 calc R . .
H2B H 0.0526 0.5981 0.6735 0.041 Uiso 1 1 calc R . .
C51 C 0.21832(12) 0.2482(3) 0.86465(16) 0.0435(5) Uani 1 1 d . . .
H51A H 0.2730 0.2387 0.8749 0.052 Uiso 1 1 calc R . .
H51B H 0.1930 0.2074 0.9257 0.052 Uiso 1 1 calc R . .
H51C H 0.2049 0.3671 0.8524 0.052 Uiso 1 1 calc R . .
C3 C 0.12372(10) 0.3932(2) 0.64364(13) 0.0315(4) Uani 1 1 d . . .
H3 H 0.1774 0.4292 0.6536 0.038 Uiso 1 1 calc R . .
C81 C 0.15267(12) 0.2640(3) 0.37893(14) 0.0424(5) Uani 1 1 d . . .
H81A H 0.1849 0.3221 0.3302 0.051 Uiso 1 1 calc R . .
H81B H 0.1003 0.2666 0.3538 0.051 Uiso 1 1 calc R . .
H81C H 0.1692 0.1460 0.3866 0.051 Uiso 1 1 calc R . .
C6 C 0.09825(11) 0.0332(2) 0.67415(14) 0.0366(5) Uani 1 1 d . . .
H6A H 0.0429 0.0244 0.6657 0.044 Uiso 1 1 calc R . .
H6B H 0.1180 -0.0803 0.6926 0.044 Uiso 1 1 calc R . .
C7 C 0.13201(10) 0.0897(2) 0.57370(13) 0.0338(5) Uani 1 1 d . . .
H7A H 0.1874 0.0751 0.5771 0.041 Uiso 1 1 calc R . .
H7B H 0.1118 0.0183 0.5174 0.041 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
O50 0.0383(8) 0.0361(7) 0.0360(7) -0.0006(5) -0.0048(5) 0.0027(5)
O9 0.0335(7) 0.0261(7) 0.0379(7) -0.0027(5) -0.0057(5) 0.0036(5)
O80 0.0415(8) 0.0327(7) 0.0304(7) -0.0020(5) 0.0016(5) -0.0002(5)
O4 0.0390(7) 0.0342(7) 0.0305(7) -0.0005(5) 0.0006(5) 0.0055(5)
C8 0.0307(9) 0.0288(9) 0.0302(9) -0.0002(7) -0.0018(7) 0.0032(7)
C1 0.0326(10) 0.0288(9) 0.0324(9) -0.0022(7) -0.0027(7) 0.0040(7)
C5 0.0367(10) 0.0328(10) 0.0340(9) 0.0041(8) -0.0016(8) 0.0020(8)
C2 0.0404(11) 0.0283(9) 0.0329(9) -0.0033(7) -0.0058(8) 0.0037(7)
C51 0.0445(12) 0.0419(11) 0.0438(11) -0.0045(9) -0.0100(9) 0.0001(9)
C3 0.0345(10) 0.0280(9) 0.0317(9) -0.0013(7) -0.0014(7) 0.0022(7)
C81 0.0529(13) 0.0421(11) 0.0323(10) -0.0043(8) 0.0053(9) 0.0015(9)
C6 0.0434(11) 0.0300(9) 0.0363(10) 0.0019(8) -0.0033(8) 0.0003(8)
C7 0.0393(10) 0.0273(9) 0.0344(9) -0.0032(8) -0.0043(8) 0.0046(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
O50 C5 1.409(2) . ?
O50 C51 1.425(2) . ?
O9 C8 1.419(2) . ?
O9 C1 1.454(2) . ?
O80 C8 1.425(2) . ?
O80 C81 1.427(2) . ?
O4 C5 1.417(2) . ?
O4 C3 1.436(2) . ?
C8 C7 1.512(2) . ?
C8 C3 1.528(2) . ?
C1 C1 1.515(3) 5_566 ?
C1 C2 1.538(2) . ?
C5 C6 1.515(3) . ?
C2 C3 1.523(2) . ?
C6 C7 1.524(2) . ?

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
C5 O50 C51 112.60(14) . . ?
C8 O9 C1 108.96(12) . . ?
C8 O80 C81 114.45(14) . . ?
C5 O4 C3 115.08(13) . . ?
O9 C8 O80 110.81(13) . . ?
O9 C8 C7 108.48(14) . . ?
O80 C8 C7 113.38(14) . . ?
O9 C8 C3 104.52(13) . . ?
O80 C8 C3 103.90(14) . . ?
C7 C8 C3 115.37(14) . . ?
O9 C1 C1 108.21(17) . 5_566 ?
O9 C1 C2 106.27(13) . . ?
C1 C1 C2 113.63(19) 5_566 . ?
O50 C5 O4 112.14(14) . . ?
O50 C5 C6 107.86(15) . . ?
O4 C5 C6 111.78(14) . . ?
C3 C2 C1 103.59(14) . . ?
O4 C3 C2 106.21(14) . . ?
O4 C3 C8 111.73(14) . . ?
C2 C3 C8 101.64(13) . . ?
C5 C6 C7 111.28(15) . . ?
C8 C7 C6 110.35(14) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.078