# 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 F² against ALL reflections.  The weighted R-factor wR and

goodness of fit S are based on F², conventional R-factors R are based

on F, with F set to zero for negative F². The threshold expression of

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement.  R-factors based

on F² 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/[σ²(Fo²)+(0.0603P)²+0.0762P] where P=(Fo²+2Fc²)/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 . .






_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







