data_leo242 
  
_audit_creation_method            SHELXTL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C13 H20 O7' 
_chemical_formula_weight          288.29 
  
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            Hexagonal 
_symmetry_space_group_name_H-M    R-3 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-y, x-y, z' 
 '-x+y, -x, z' 
 'x+2/3, y+1/3, z+1/3' 
 '-y+2/3, x-y+1/3, z+1/3' 
 '-x+y+2/3, -x+1/3, z+1/3' 
 'x+1/3, y+2/3, z+2/3' 
 '-y+1/3, x-y+2/3, z+2/3' 
 '-x+y+1/3, -x+2/3, z+2/3' 
 '-x, -y, -z' 
 'y, -x+y, -z' 
 'x-y, x, -z' 
 '-x+2/3, -y+1/3, -z+1/3' 
 'y+2/3, -x+y+1/3, -z+1/3' 
 'x-y+2/3, x+1/3, -z+1/3' 
 '-x+1/3, -y+2/3, -z+2/3' 
 'y+1/3, -x+y+2/3, -z+2/3' 
 'x-y+1/3, x+2/3, -z+2/3' 
  
_cell_length_a                    33.1098(13) 
_cell_length_b                    33.1098(13) 
_cell_length_c                    6.3799(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 120.00 
_cell_volume                      6057.0(4) 
_cell_formula_units_Z             18 
_cell_measurement_temperature     88(2) 
_cell_measurement_reflns_used     8496 
_cell_measurement_theta_min       2.46 
_cell_measurement_theta_max       28.72 
  
_exptl_crystal_description        hexagon 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.28 
_exptl_crystal_size_mid           0.18 
_exptl_crystal_size_min           0.14 
_exptl_crystal_density_meas       none 
_exptl_crystal_density_diffrn     1.423 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              2772 
_exptl_absorpt_coefficient_mu     0.116 
_exptl_absorpt_correction_type    numerical 
_exptl_absorpt_correction_T_min   0.9678 
_exptl_absorpt_correction_T_max   0.9838 
_exptl_absorpt_process_details    'Bruker SADABS' 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       88(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 APEX-II CCD' 
_diffrn_measurement_method        '\f and \w scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             23307 
_diffrn_reflns_av_R_equivalents   0.0264 
_diffrn_reflns_av_sigmaI/netI     0.0147 
_diffrn_reflns_limit_h_min        -42 
_diffrn_reflns_limit_h_max        42 
_diffrn_reflns_limit_k_min        -42 
_diffrn_reflns_limit_k_max        42 
_diffrn_reflns_limit_l_min        -8 
_diffrn_reflns_limit_l_max        8 
_diffrn_reflns_theta_min          2.13 
_diffrn_reflns_theta_max          27.10 
_reflns_number_total              2968 
_reflns_number_gt                 2622 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_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^)+(0.0549P)^2^+7.9802P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    difmap 
_refine_ls_hydrogen_treatment     refall 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2968 
_refine_ls_number_parameters      261 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0410 
_refine_ls_R_factor_gt            0.0355 
_refine_ls_wR_factor_ref          0.0976 
_refine_ls_wR_factor_gt           0.0931 
_refine_ls_goodness_of_fit_ref    1.034 
_refine_ls_restrained_S_all       1.034 
_refine_ls_shift/su_max           0.001 
_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 0.72892(3) 0.20173(3) 0.00030(14) 0.0188(2) Uani 1 1 d . . . 
O2 O 0.67850(3) 0.21858(3) 0.15065(14) 0.0164(2) Uani 1 1 d . . . 
O3 O 0.60303(3) 0.19859(3) 0.05709(14) 0.0191(2) Uani 1 1 d . . . 
O4 O 0.62956(3) 0.16441(3) 0.62523(13) 0.01462(19) Uani 1 1 d . . . 
O5 O 0.70636(3) 0.16792(3) 0.48895(14) 0.0168(2) Uani 1 1 d . . . 
O6 O 0.55399(3) 0.05396(3) 0.40473(15) 0.0219(2) Uani 1 1 d . . . 
O7 O 0.57534(3) 0.07761(3) 0.73755(14) 0.0171(2) Uani 1 1 d . . . 
C1 C 0.69127(4) 0.18787(4) 0.08094(18) 0.0147(2) Uani 1 1 d . . . 
C2 C 0.65235(4) 0.13801(4) 0.11156(18) 0.0133(2) Uani 1 1 d . . . 
C3 C 0.62979(4) 0.19429(4) 0.21489(19) 0.0150(2) Uani 1 1 d . . . 
C4 C 0.62140(4) 0.13022(4) 0.47180(18) 0.0131(2) Uani 1 1 d . . . 
C5 C 0.66494(4) 0.12414(4) 0.46640(19) 0.0135(2) Uani 1 1 d . . . 
C6 C 0.66510(4) 0.10692(4) 0.24441(18) 0.0132(2) Uani 1 1 d . . . 
C7 C 0.61613(4) 0.14346(4) 0.24151(19) 0.0137(2) Uani 1 1 d . . . 
C8 C 0.61075(5) 0.24504(5) 0.0429(2) 0.0231(3) Uani 1 1 d . . . 
C9 C 0.57911(4) 0.08299(4) 0.52997(19) 0.0144(2) Uani 1 1 d . . . 
C10 C 0.53417(5) 0.03655(5) 0.8144(2) 0.0209(3) Uani 1 1 d . . . 
C11 C 0.70883(4) 0.10452(4) 0.18676(19) 0.0149(2) Uani 1 1 d . . . 
C12 C 0.70795(5) 0.09149(5) -0.0443(2) 0.0189(3) Uani 1 1 d . . . 
C13 C 0.71218(5) 0.06866(5) 0.3263(2) 0.0195(3) Uani 1 1 d . . . 
H4A H 0.6034(7) 0.1602(7) 0.663(3) 0.035(5) Uiso 1 1 d . . . 
H5A H 0.7023(6) 0.1827(7) 0.582(3) 0.031(5) Uiso 1 1 d . . . 
H2A H 0.6408(5) 0.1248(5) -0.024(2) 0.016(4) Uiso 1 1 d . . . 
H3A H 0.6286(5) 0.2095(5) 0.345(2) 0.013(3) Uiso 1 1 d . . . 
H5B H 0.6622(5) 0.1018(5) 0.572(2) 0.015(4) Uiso 1 1 d . . . 
H6A H 0.6375(5) 0.0752(5) 0.233(2) 0.012(3) Uiso 1 1 d . . . 
H7A H 0.5846(5) 0.1246(5) 0.195(2) 0.014(4) Uiso 1 1 d . . . 
H8A H 0.5858(7) 0.2442(7) -0.039(3) 0.039(5) Uiso 1 1 d . . . 
H8B H 0.6413(6) 0.2664(6) -0.021(3) 0.029(4) Uiso 1 1 d . . . 
H8C H 0.6083(7) 0.2559(7) 0.182(3) 0.033(5) Uiso 1 1 d . . . 
H10A H 0.5391(7) 0.0368(7) 0.957(4) 0.042(5) Uiso 1 1 d . . . 
H10B H 0.5318(7) 0.0093(7) 0.761(3) 0.034(5) Uiso 1 1 d . . . 
H10C H 0.5079(7) 0.0384(7) 0.784(3) 0.042(5) Uiso 1 1 d . . . 
H11A H 0.7363(5) 0.1354(5) 0.210(2) 0.013(3) Uiso 1 1 d . . . 
H12A H 0.7343(6) 0.0861(6) -0.072(3) 0.023(4) Uiso 1 1 d . . . 
H12B H 0.7096(6) 0.1154(6) -0.135(3) 0.027(4) Uiso 1 1 d . . . 
H12C H 0.6788(6) 0.0619(6) -0.076(3) 0.025(4) Uiso 1 1 d . . . 
H13A H 0.7386(6) 0.0648(6) 0.288(3) 0.022(4) Uiso 1 1 d . . . 
H13B H 0.6841(6) 0.0387(6) 0.312(3) 0.026(4) Uiso 1 1 d . . . 
H13C H 0.7161(6) 0.0782(6) 0.477(3) 0.026(4) Uiso 1 1 d . . . 
  
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 0.0163(4) 0.0181(4) 0.0202(5) 0.0039(3) 0.0039(3) 0.0073(4) 
O2 0.0142(4) 0.0140(4) 0.0202(5) 0.0012(3) 0.0007(3) 0.0066(3) 
O3 0.0187(5) 0.0218(5) 0.0183(5) 0.0057(3) -0.0014(3) 0.0112(4) 
O4 0.0139(4) 0.0147(4) 0.0136(4) -0.0017(3) 0.0001(3) 0.0059(3) 
O5 0.0130(4) 0.0179(4) 0.0158(4) -0.0050(3) -0.0010(3) 0.0049(4) 
O6 0.0200(5) 0.0173(5) 0.0184(5) -0.0009(4) -0.0021(4) 0.0017(4) 
O7 0.0150(4) 0.0159(4) 0.0148(4) 0.0038(3) 0.0015(3) 0.0035(4) 
C1 0.0162(6) 0.0157(6) 0.0120(5) 0.0013(4) -0.0016(4) 0.0078(5) 
C2 0.0138(5) 0.0145(6) 0.0105(5) -0.0007(4) -0.0012(4) 0.0061(5) 
C3 0.0135(6) 0.0173(6) 0.0138(6) 0.0023(4) -0.0001(4) 0.0075(5) 
C4 0.0131(5) 0.0127(5) 0.0114(5) -0.0004(4) -0.0004(4) 0.0050(5) 
C5 0.0123(5) 0.0136(6) 0.0125(5) 0.0013(4) -0.0010(4) 0.0048(5) 
C6 0.0130(5) 0.0124(5) 0.0127(5) 0.0005(4) -0.0007(4) 0.0051(5) 
C7 0.0123(6) 0.0143(6) 0.0131(5) 0.0004(4) -0.0016(4) 0.0055(5) 
C8 0.0219(7) 0.0248(7) 0.0272(7) 0.0119(6) 0.0069(5) 0.0150(6) 
C9 0.0128(5) 0.0154(6) 0.0149(6) 0.0015(4) 0.0002(4) 0.0070(5) 
C10 0.0168(6) 0.0173(6) 0.0216(7) 0.0062(5) 0.0050(5) 0.0034(5) 
C11 0.0151(6) 0.0154(6) 0.0142(6) -0.0001(4) -0.0003(4) 0.0076(5) 
C12 0.0223(7) 0.0205(6) 0.0156(6) -0.0019(5) 0.0001(5) 0.0119(6) 
C13 0.0211(7) 0.0216(7) 0.0199(7) 0.0031(5) 0.0011(5) 0.0138(6) 
  
_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 C1 1.2070(15) . ? 
O2 C1 1.3566(15) . ? 
O2 C3 1.4557(14) . ? 
O3 C3 1.3948(14) . ? 
O3 C8 1.4302(16) . ? 
O4 C4 1.4168(14) . ? 
O5 C5 1.4193(14) . ? 
O6 C9 1.2062(15) . ? 
O7 C9 1.3337(15) . ? 
O7 C10 1.4469(15) . ? 
C1 C2 1.5156(16) . ? 
C2 C7 1.5410(17) . ? 
C2 C6 1.5459(16) . ? 
C3 C7 1.5180(17) . ? 
C4 C9 1.5343(16) . ? 
C4 C5 1.5524(17) . ? 
C4 C7 1.5678(16) . ? 
C5 C6 1.5277(16) . ? 
C6 C11 1.5340(16) . ? 
C11 C13 1.5318(17) . ? 
C11 C12 1.5324(17) . ? 
  
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 
C1 O2 C3 110.65(9) . . ? 
C3 O3 C8 111.99(10) . . ? 
C9 O7 C10 116.31(10) . . ? 
O1 C1 O2 120.29(11) . . ? 
O1 C1 C2 128.54(11) . . ? 
O2 C1 C2 111.12(10) . . ? 
C1 C2 C7 103.26(10) . . ? 
C1 C2 C6 115.43(10) . . ? 
C7 C2 C6 105.70(9) . . ? 
O3 C3 O2 108.99(9) . . ? 
O3 C3 C7 109.97(10) . . ? 
O2 C3 C7 106.12(9) . . ? 
O4 C4 C9 111.07(9) . . ? 
O4 C4 C5 107.49(9) . . ? 
C9 C4 C5 107.86(9) . . ? 
O4 C4 C7 115.30(10) . . ? 
C9 C4 C7 109.83(9) . . ? 
C5 C4 C7 104.83(9) . . ? 
O5 C5 C6 107.05(9) . . ? 
O5 C5 C4 110.56(10) . . ? 
C6 C5 C4 104.21(9) . . ? 
C5 C6 C11 114.90(10) . . ? 
C5 C6 C2 101.94(9) . . ? 
C11 C6 C2 118.82(10) . . ? 
C3 C7 C2 104.58(10) . . ? 
C3 C7 C4 113.69(10) . . ? 
C2 C7 C4 105.63(9) . . ? 
O6 C9 O7 124.76(11) . . ? 
O6 C9 C4 124.49(11) . . ? 
O7 C9 C4 110.68(10) . . ? 
C13 C11 C12 109.83(11) . . ? 
C13 C11 C6 109.69(10) . . ? 
C12 C11 C6 111.09(10) . . ? 
  
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 
C3 O2 C1 O1 172.17(11) . . . . ? 
C3 O2 C1 C2 -5.46(13) . . . . ? 
O1 C1 C2 C7 174.70(12) . . . . ? 
O2 C1 C2 C7 -7.92(12) . . . . ? 
O1 C1 C2 C6 59.87(17) . . . . ? 
O2 C1 C2 C6 -122.74(11) . . . . ? 
C8 O3 C3 O2 -70.91(12) . . . . ? 
C8 O3 C3 C7 173.14(10) . . . . ? 
C1 O2 C3 O3 -101.55(11) . . . . ? 
C1 O2 C3 C7 16.84(12) . . . . ? 
O4 C4 C5 O5 -39.16(12) . . . . ? 
C9 C4 C5 O5 -159.00(9) . . . . ? 
C7 C4 C5 O5 84.00(11) . . . . ? 
O4 C4 C5 C6 -153.87(9) . . . . ? 
C9 C4 C5 C6 86.29(11) . . . . ? 
C7 C4 C5 C6 -30.71(11) . . . . ? 
O5 C5 C6 C11 54.69(13) . . . . ? 
C4 C5 C6 C11 171.85(9) . . . . ? 
O5 C5 C6 C2 -75.20(11) . . . . ? 
C4 C5 C6 C2 41.96(11) . . . . ? 
C1 C2 C6 C5 75.84(12) . . . . ? 
C7 C2 C6 C5 -37.58(11) . . . . ? 
C1 C2 C6 C11 -51.56(14) . . . . ? 
C7 C2 C6 C11 -164.98(10) . . . . ? 
O3 C3 C7 C2 96.89(11) . . . . ? 
O2 C3 C7 C2 -20.85(12) . . . . ? 
O3 C3 C7 C4 -148.40(10) . . . . ? 
O2 C3 C7 C4 93.86(11) . . . . ? 
C1 C2 C7 C3 17.26(12) . . . . ? 
C6 C2 C7 C3 138.90(10) . . . . ? 
C1 C2 C7 C4 -102.99(10) . . . . ? 
C6 C2 C7 C4 18.64(12) . . . . ? 
O4 C4 C7 C3 11.09(14) . . . . ? 
C9 C4 C7 C3 137.48(10) . . . . ? 
C5 C4 C7 C3 -106.89(11) . . . . ? 
O4 C4 C7 C2 125.18(10) . . . . ? 
C9 C4 C7 C2 -108.43(11) . . . . ? 
C5 C4 C7 C2 7.20(12) . . . . ? 
C10 O7 C9 O6 -9.00(18) . . . . ? 
C10 O7 C9 C4 173.97(10) . . . . ? 
O4 C4 C9 O6 150.73(12) . . . . ? 
C5 C4 C9 O6 -91.71(14) . . . . ? 
C7 C4 C9 O6 21.99(16) . . . . ? 
O4 C4 C9 O7 -32.22(13) . . . . ? 
C5 C4 C9 O7 85.33(12) . . . . ? 
C7 C4 C9 O7 -160.96(10) . . . . ? 
C5 C6 C11 C13 63.86(13) . . . . ? 
C2 C6 C11 C13 -175.10(10) . . . . ? 
C5 C6 C11 C12 -174.52(10) . . . . ? 
C2 C6 C11 C12 -53.48(14) . . . . ? 
  
_diffrn_measured_fraction_theta_max    1.000 
_diffrn_reflns_theta_full              25.50 
_diffrn_measured_fraction_theta_full   1.000 
_refine_diff_density_max    0.446 
_refine_diff_density_min   -0.197 
_refine_diff_density_rms    0.047