# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2002

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

loop_
_publ_author_name
'Francois Carreaux'
'B. Carboni'
'Michael Deligny'
'G. Dujardin'
_publ_contact_author_address     
;
Institut de chimie
Université de Rennes 1
Campus de Beaulieu
Rennes
35042
FRANCE
;

_publ_contact_author_email       FRANCOIS.CARREAUX@UNIV-RENNES1.FR

_publ_contact_author_name        'Dr Francois Carreaux'

data_dm
_database_code_CSD               188816

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 O5'
_chemical_formula_weight         268.30

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   P21

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

_cell_length_a                   8.972(4)
_cell_length_b                   6.264(2)
_cell_length_c                   12.190(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.00(4)
_cell_angle_gamma                90.00
_cell_volume                     672.5(4)
_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       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   ?
_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     0.71069
_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            1696
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         26.97
_reflns_number_total             1597
_reflns_number_gt                1459
_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^)+(0.0603P)^2^+0.0762P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(11)
_refine_ls_number_reflns         1597
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.052
_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
O1 O 0.27557(15) 0.5438(2) 0.69147(10) 0.0308(3) Uani 1 1 d . . .
O2 O 0.36040(17) 0.7061(3) 0.90359(12) 0.0389(4) Uani 1 1 d . . .
H2A H 0.416(3) 0.680(6) 0.962(2) 0.050 Uiso 1 1 d . . .
O3 O 0.44304(19) 0.1368(3) 0.89684(13) 0.0447(4) Uani 1 1 d . . .
H3A H 0.404(3) 0.032(6) 0.874(2) 0.050 Uiso 1 1 d . . .
O4 O 0.3254(2) 0.0037(3) 0.67521(15) 0.0460(4) Uani 1 1 d . . .
H4A H 0.363(3) -0.095(6) 0.685(2) 0.050 Uiso 1 1 d . . .
O5 O 0.27997(15) 0.5948(3) 0.50778(11) 0.0365(4) Uani 1 1 d . . .
C1 C -0.0133(2) 0.4815(4) 0.90905(16) 0.0390(5) Uani 1 1 d . . .
H1 H 0.0188 0.3557 0.9468 0.047 Uiso 1 1 calc R . .
C2 C -0.1652(2) 0.5402(5) 0.89399(18) 0.0461(6) Uani 1 1 d . . .
H2 H -0.2338 0.4542 0.9219 0.055 Uiso 1 1 calc R . .
C3 C -0.2143(2) 0.7262(5) 0.83759(19) 0.0496(6) Uani 1 1 d . . .
H3 H -0.3159 0.7659 0.8275 0.059 Uiso 1 1 calc R . .
C4 C -0.1119(3) 0.8525(5) 0.7965(2) 0.0509(6) Uani 1 1 d . . .
H4 H -0.1450 0.9771 0.7579 0.061 Uiso 1 1 calc R . .
C5 C 0.0410(2) 0.7954(4) 0.81206(17) 0.0413(5) Uani 1 1 d . . .
H5 H 0.1094 0.8827 0.7847 0.050 Uiso 1 1 calc R . .
C6 C 0.0913(2) 0.6080(3) 0.86850(14) 0.0313(4) Uani 1 1 d . . .
C7 C 0.2546(2) 0.5309(3) 0.88409(15) 0.0308(4) Uani 1 1 d . . .
H7 H 0.2741 0.4381 0.9500 0.037 Uiso 1 1 calc R . .
C8 C 0.2802(2) 0.3995(3) 0.78334(14) 0.0281(4) Uani 1 1 d . . .
H8 H 0.1969 0.2968 0.7642 0.034 Uiso 1 1 calc R . .
C9 C 0.4315(2) 0.2773(3) 0.80328(16) 0.0332(4) Uani 1 1 d . . .
H9 H 0.5143 0.3814 0.8194 0.040 Uiso 1 1 calc R . .
C10 C 0.4469(2) 0.1562(4) 0.69723(19) 0.0394(5) Uani 1 1 d . . .
H10 H 0.5453 0.0837 0.7073 0.047 Uiso 1 1 calc R . .
C11 C 0.4302(2) 0.3132(4) 0.60009(19) 0.0418(5) Uani 1 1 d . . .
H11A H 0.5151 0.4118 0.6124 0.050 Uiso 1 1 calc R . .
H11B H 0.4320 0.2358 0.5314 0.050 Uiso 1 1 calc R . .
C12 C 0.2834(2) 0.4365(3) 0.58864(15) 0.0295(4) Uani 1 1 d . . .
H12 H 0.1965 0.3402 0.5678 0.035 Uiso 1 1 calc R . .
C13 C 0.1338(2) 0.6932(4) 0.47321(17) 0.0385(5) Uani 1 1 d . . .
H13A H 0.0963 0.7444 0.5380 0.046 Uiso 1 1 calc R . .
H13B H 0.0619 0.5900 0.4345 0.046 Uiso 1 1 calc R . .
C14 C 0.1501(2) 0.8760(4) 0.39700(18) 0.0440(5) Uani 1 1 d . . .
H14A H 0.0534 0.9443 0.3738 0.053 Uiso 1 1 calc R . .
H14B H 0.1856 0.8237 0.3326 0.053 Uiso 1 1 calc R . .
H14C H 0.2217 0.9771 0.4358 0.053 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
O1 0.0397(7) 0.0229(7) 0.0283(6) 0.0024(5) 0.0027(5) 0.0050(6)
O2 0.0456(8) 0.0279(8) 0.0359(7) 0.0000(6) -0.0112(6) -0.0070(7)
O3 0.0534(9) 0.0252(8) 0.0443(8) 0.0055(7) -0.0186(6) -0.0010(7)
O4 0.0588(10) 0.0224(8) 0.0531(9) -0.0032(8) 0.0011(7) 0.0018(7)
O5 0.0359(7) 0.0383(9) 0.0373(7) 0.0097(7) 0.0116(5) 0.0056(7)
C1 0.0463(11) 0.0378(12) 0.0308(9) 0.0054(9) 0.0024(8) -0.0016(10)
C2 0.0409(10) 0.0562(16) 0.0402(11) -0.0014(11) 0.0051(8) -0.0090(11)
C3 0.0403(11) 0.0638(17) 0.0435(12) -0.0010(13) 0.0051(9) 0.0098(12)
C4 0.0529(13) 0.0459(14) 0.0521(13) 0.0101(12) 0.0059(10) 0.0153(12)
C5 0.0475(11) 0.0360(12) 0.0412(10) 0.0072(10) 0.0109(8) 0.0042(10)
C6 0.0403(9) 0.0302(10) 0.0219(8) -0.0015(8) 0.0025(7) 0.0005(8)
C7 0.0381(9) 0.0252(9) 0.0260(8) 0.0034(8) -0.0016(6) -0.0014(8)
C8 0.0291(8) 0.0232(10) 0.0287(8) 0.0033(7) -0.0028(6) -0.0015(7)
C9 0.0295(8) 0.0230(9) 0.0420(10) 0.0046(9) -0.0064(7) -0.0011(8)
C10 0.0313(9) 0.0306(12) 0.0552(12) 0.0049(10) 0.0053(8) 0.0093(9)
C11 0.0403(10) 0.0351(12) 0.0539(12) 0.0057(11) 0.0186(9) 0.0082(10)
C12 0.0317(9) 0.0270(10) 0.0303(8) 0.0011(8) 0.0070(7) 0.0013(8)
C13 0.0339(9) 0.0461(13) 0.0344(9) 0.0072(10) 0.0035(7) 0.0037(10)
C14 0.0440(11) 0.0471(14) 0.0388(11) 0.0099(11) 0.0028(8) 0.0039(11)

_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
O1 C8 1.434(2) . ?
O1 C12 1.436(2) . ?
O2 C7 1.440(2) . ?
O2 H2A 0.81(3) . ?
O3 C9 1.428(3) . ?
O3 H3A 0.77(4) . ?
O4 C10 1.435(3) . ?
O4 H4A 0.70(4) . ?
O5 C12 1.394(2) . ?
O5 C13 1.438(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.520(3) . ?
C7 C8 1.532(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.537(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.528(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.524(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.510(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9800 . ?
C13 C14 1.499(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C8 O1 C12 112.85(15) . . ?
C7 O2 H2A 106(2) . . ?
C9 O3 H3A 106(2) . . ?
C10 O4 H4A 103(3) . . ?
C12 O5 C13 114.09(14) . . ?
C2 C1 C6 120.9(2) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 118.68(19) . . ?
C1 C6 C7 118.35(19) . . ?
C5 C6 C7 122.93(19) . . ?
O2 C7 C6 111.58(18) . . ?
O2 C7 C8 110.30(15) . . ?
C6 C7 C8 111.02(14) . . ?
O2 C7 H7 107.9 . . ?
C6 C7 H7 107.9 . . ?
C8 C7 H7 107.9 . . ?
O1 C8 C7 107.54(16) . . ?
O1 C8 C9 109.29(14) . . ?
C7 C8 C9 113.82(15) . . ?
O1 C8 H8 108.7 . . ?
C7 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
O3 C9 C10 111.43(18) . . ?
O3 C9 C8 111.14(16) . . ?
C10 C9 C8 109.47(15) . . ?
O3 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
O4 C10 C11 108.99(18) . . ?
O4 C10 C9 107.49(16) . . ?
C11 C10 C9 109.01(18) . . ?
O4 C10 H10 110.4 . . ?
C11 C10 H10 110.4 . . ?
C9 C10 H10 110.4 . . ?
C12 C11 C10 110.88(16) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O5 C12 O1 106.64(16) . . ?
O5 C12 C11 109.30(15) . . ?
O1 C12 C11 110.23(16) . . ?
O5 C12 H12 110.2 . . ?
O1 C12 H12 110.2 . . ?
C11 C12 H12 110.2 . . ?
O5 C13 C14 108.54(16) . . ?
O5 C13 H13A 110.0 . . ?
C14 C13 H13A 110.0 . . ?
O5 C13 H13B 110.0 . . ?
C14 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C6 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C1 C6 C7 -177.85(19) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 C6 C7 177.2(2) . . . . ?
C1 C6 C7 O2 -144.92(17) . . . . ?
C5 C6 C7 O2 37.4(2) . . . . ?
C1 C6 C7 C8 91.6(2) . . . . ?
C5 C6 C7 C8 -86.0(2) . . . . ?
C12 O1 C8 C7 -174.29(13) . . . . ?
C12 O1 C8 C9 61.71(18) . . . . ?
O2 C7 C8 O1 -53.19(18) . . . . ?
C6 C7 C8 O1 71.03(19) . . . . ?
O2 C7 C8 C9 68.0(2) . . . . ?
C6 C7 C8 C9 -167.76(16) . . . . ?
O1 C8 C9 O3 177.96(15) . . . . ?
C7 C8 C9 O3 57.7(2) . . . . ?
O1 C8 C9 C10 -58.5(2) . . . . ?
C7 C8 C9 C10 -178.75(17) . . . . ?
O3 C9 C10 O4 60.8(2) . . . . ?
C8 C9 C10 O4 -62.6(2) . . . . ?
O3 C9 C10 C11 178.78(16) . . . . ?
C8 C9 C10 C11 55.4(2) . . . . ?
O4 C10 C11 C12 62.3(2) . . . . ?
C9 C10 C11 C12 -54.7(2) . . . . ?
C13 O5 C12 O1 -73.0(2) . . . . ?
C13 O5 C12 C11 167.84(18) . . . . ?
C8 O1 C12 O5 -179.21(13) . . . . ?
C8 O1 C12 C11 -60.7(2) . . . . ?
C10 C11 C12 O5 173.25(17) . . . . ?
C10 C11 C12 O1 56.4(2) . . . . ?
C12 O5 C13 C14 173.44(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.97
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.040