# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Didier Bourissou'
'Colin Bonduelle'
'Olivier Thillaye du Boullay'
'Blanca Martin-Vaca'

_publ_contact_author_name        'Didier Bourissou'
_publ_contact_author_address     
;
Laboratoire Heterochimie Fondamentale et Appliquee
Universite Paul Sabatier
Bat 2 R1 - 2eme etage
118 route de Narbonne
Toulouse cedex
31062
FRANCE
;

_publ_contact_author_email       DBOURISS@CHIMIE.UPS-TLSE.FR

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Laboratoire Heterochimie Fondamentale et Appliquee
Universite Paul Sabatier
Bat 2 R1 - 2eme etage
118 route de Narbonne
Toulouse cedex
31062
FRANCE
;

data_od03m
_database_code_depnum_ccdc_archive 'CCDC 674939'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 O6'
_chemical_formula_weight         264.23

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   5.6733(14)
_cell_length_b                   7.7930(19)
_cell_length_c                   27.552(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1218.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    695
_cell_measurement_theta_min      2.958
_cell_measurement_theta_max      21.514

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_correction_T_min  0.539389
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'Bruker CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4778
_diffrn_reflns_av_R_equivalents  0.1047
_diffrn_reflns_av_sigmaI/netI    0.1214
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         5.15
_diffrn_reflns_theta_max         21.96
_reflns_number_total             1466
_reflns_number_gt                938
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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^)+(0.0349P)^2^+0.0000P] 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    constr

_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   -2(3)
_refine_ls_number_reflns         1466
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_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 -0.0199(7) 0.3946(4) 0.93447(12) 0.0288(10) Uani 1 1 d . . .
O2 O -0.1361(7) 0.4911(4) 1.00666(11) 0.0298(10) Uani 1 1 d . . .
O3 O -0.3467(8) 0.2841(5) 0.96928(14) 0.0489(13) Uani 1 1 d . . .
O4 O 0.1609(9) 0.6670(5) 1.02661(13) 0.0453(13) Uani 1 1 d . . .
O5 O 0.5635(7) 0.5331(5) 0.87251(12) 0.0377(11) Uani 1 1 d . . .
O6 O 0.4030(7) 0.5208(4) 0.79788(11) 0.0312(11) Uani 1 1 d . . .
C1 C 0.1521(11) 0.5241(7) 0.94806(16) 0.0237(13) Uani 1 1 d . . .
H1 H 0.3142 0.4737 0.9488 0.028 Uiso 1 1 calc R . .
C2 C -0.1811(12) 0.3797(8) 0.9688(2) 0.0305(16) Uani 1 1 d . . .
C3 C 0.0747(10) 0.5718(7) 0.99776(19) 0.0272(15) Uani 1 1 d . . .
C4 C 0.1425(13) 0.6755(6) 0.91335(15) 0.0285(15) Uani 1 1 d . . .
H4A H 0.2721 0.7558 0.9214 0.034 Uiso 1 1 calc R . .
H4B H -0.0081 0.7373 0.9182 0.034 Uiso 1 1 calc R . .
C5 C 0.1632(11) 0.6244(7) 0.85992(17) 0.0251(14) Uani 1 1 d . . .
H5A H 0.0414 0.5371 0.8527 0.030 Uiso 1 1 calc R . .
H5B H 0.1294 0.7263 0.8396 0.030 Uiso 1 1 calc R . .
C6 C 0.3964(11) 0.5548(7) 0.84594(17) 0.0259(15) Uani 1 1 d . . .
C7 C 0.6150(10) 0.4436(7) 0.77908(18) 0.0351(16) Uani 1 1 d . . .
H7A H 0.6045 0.3171 0.7816 0.042 Uiso 1 1 calc R . .
H7B H 0.7528 0.4823 0.7982 0.042 Uiso 1 1 calc R . .
C8 C 0.6440(11) 0.4955(6) 0.72679(16) 0.0214(13) Uani 1 1 d . . .
C9 C 0.4687(11) 0.4580(7) 0.6933(2) 0.0316(15) Uani 1 1 d . . .
H9 H 0.3322 0.3965 0.7031 0.038 Uiso 1 1 calc R . .
C10 C 0.4937(13) 0.5106(7) 0.64543(19) 0.0404(17) Uani 1 1 d . . .
H10 H 0.3730 0.4861 0.6226 0.048 Uiso 1 1 calc R . .
C11 C 0.6936(12) 0.5984(7) 0.6309(2) 0.0339(17) Uani 1 1 d . . .
H11 H 0.7102 0.6352 0.5982 0.041 Uiso 1 1 calc R . .
C12 C 0.8648(13) 0.6312(7) 0.66366(19) 0.0342(16) Uani 1 1 d . . .
H12 H 1.0046 0.6882 0.6537 0.041 Uiso 1 1 calc R . .
C13 C 0.8384(11) 0.5826(6) 0.71142(18) 0.0305(16) Uani 1 1 d . . .
H13 H 0.9584 0.6104 0.7341 0.037 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 0.033(3) 0.023(2) 0.031(2) -0.0010(17) 0.006(2) -0.007(2)
O2 0.036(3) 0.020(2) 0.033(2) 0.0031(19) 0.011(2) 0.007(2)
O3 0.041(3) 0.043(3) 0.063(3) 0.020(2) -0.007(3) -0.021(3)
O4 0.075(4) 0.031(2) 0.030(2) -0.004(2) -0.006(3) -0.005(3)
O5 0.037(3) 0.047(3) 0.029(2) -0.002(2) -0.004(2) -0.002(2)
O6 0.038(3) 0.034(2) 0.022(2) -0.0005(18) -0.0022(18) -0.002(2)
C1 0.028(3) 0.020(3) 0.023(3) 0.004(3) 0.001(3) -0.009(4)
C2 0.035(5) 0.022(4) 0.034(4) 0.012(3) -0.004(4) 0.000(4)
C3 0.033(5) 0.025(4) 0.024(3) 0.005(3) 0.005(3) 0.004(3)
C4 0.046(4) 0.021(3) 0.019(3) 0.001(3) 0.002(3) -0.006(4)
C5 0.030(4) 0.022(3) 0.023(3) 0.001(2) 0.000(3) -0.007(4)
C6 0.039(5) 0.022(3) 0.017(3) 0.002(3) -0.004(3) -0.012(3)
C7 0.034(4) 0.032(3) 0.039(3) 0.001(3) 0.006(3) 0.008(4)
C8 0.024(3) 0.016(3) 0.024(3) -0.004(3) 0.001(3) 0.007(4)
C9 0.034(4) 0.027(3) 0.033(3) -0.004(3) 0.004(3) 0.007(3)
C10 0.056(4) 0.035(4) 0.030(4) -0.012(3) -0.002(3) 0.010(5)
C11 0.051(5) 0.024(4) 0.027(4) 0.000(3) 0.004(4) 0.006(4)
C12 0.041(4) 0.029(4) 0.033(4) 0.000(3) 0.006(3) 0.003(4)
C13 0.036(5) 0.025(3) 0.031(4) -0.010(3) -0.002(3) 0.000(4)

_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 C2 1.321(7) . ?
O1 C1 1.453(6) . ?
O2 C3 1.373(6) . ?
O2 C2 1.380(6) . ?
O3 C2 1.199(7) . ?
O4 C3 1.192(6) . ?
O5 C6 1.210(6) . ?
O6 C6 1.351(5) . ?
O6 C7 1.441(6) . ?
C1 C3 1.486(7) . ?
C1 C4 1.520(6) . ?
C4 C5 1.530(6) . ?
C5 C6 1.481(8) . ?
C7 C8 1.505(6) . ?
C8 C13 1.362(7) . ?
C8 C9 1.387(7) . ?
C9 C10 1.389(7) . ?
C10 C11 1.383(8) . ?
C11 C12 1.351(7) . ?
C12 C13 1.377(7) . ?

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 O1 C1 109.9(4) . . ?
C3 O2 C2 108.3(4) . . ?
C6 O6 C7 117.2(4) . . ?
O1 C1 C3 102.3(4) . . ?
O1 C1 C4 110.7(4) . . ?
C3 C1 C4 112.0(4) . . ?
O3 C2 O1 127.1(6) . . ?
O3 C2 O2 121.9(6) . . ?
O1 C2 O2 111.0(5) . . ?
O4 C3 O2 121.6(5) . . ?
O4 C3 C1 130.5(6) . . ?
O2 C3 C1 107.9(5) . . ?
C1 C4 C5 113.6(4) . . ?
C6 C5 C4 114.5(5) . . ?
O5 C6 O6 122.9(5) . . ?
O5 C6 C5 126.5(5) . . ?
O6 C6 C5 110.6(5) . . ?
O6 C7 C8 108.8(4) . . ?
C13 C8 C9 118.6(5) . . ?
C13 C8 C7 121.3(5) . . ?
C9 C8 C7 120.1(6) . . ?
C8 C9 C10 119.7(5) . . ?
C11 C10 C9 120.3(5) . . ?
C12 C11 C10 119.3(5) . . ?
C11 C12 C13 120.6(6) . . ?
C8 C13 C12 121.5(5) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        21.96
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.049

#===END