 
data_20100706aj389 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C26 H20 O8' 
_chemical_formula_weight          460.42 
  
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            Triclinic 
_symmetry_space_group_name_H-M    P-1 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
  
_cell_length_a                    9.2883(9) 
_cell_length_b                    11.2794(11) 
_cell_length_c                    11.6730(12) 
_cell_angle_alpha                 62.3560(10) 
_cell_angle_beta                  89.0080(10) 
_cell_angle_gamma                 89.8930(10) 
_cell_volume                      1083.15(19) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     173 
_cell_measurement_reflns_used     3905 
_cell_measurement_theta_min       2.19 
_cell_measurement_theta_max       28.47 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.22 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.412 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              480 
_exptl_absorpt_coefficient_mu     0.106 
_exptl_absorpt_correction_type    empirical 
_exptl_absorpt_correction_T_min   0.9766 
_exptl_absorpt_correction_T_max   0.9947 
_exptl_absorpt_process_details    
;
SADABS Sheldrick 1996
;
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       173 
_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        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.333 
_diffrn_reflns_number             5138 
_diffrn_reflns_av_R_equivalents   0.0125 
_diffrn_reflns_av_sigmaI/netI     0.0205 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -13 
_diffrn_reflns_limit_l_max        5 
_diffrn_reflns_theta_min          1.97 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              3721 
_reflns_number_gt                 3373 
_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 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)+(0.0712P)²+0.2916P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     refall 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3721 
_refine_ls_number_parameters      387 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0389 
_refine_ls_R_factor_gt            0.0356 
_refine_ls_wR_factor_ref          0.1060 
_refine_ls_wR_factor_gt           0.1021 
_refine_ls_goodness_of_fit_ref    0.984 
_refine_ls_restrained_S_all       0.984 
_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 
C1 C 0.27133(15) 0.74856(13) 0.25280(12) 0.0261(3) Uani 1 1 d . . . 
C2 C 0.16720(17) 0.82331(15) 0.27770(14) 0.0342(3) Uani 1 1 d . . . 
C3 C 0.04667(18) 0.86754(16) 0.20150(15) 0.0385(4) Uani 1 1 d . . . 
C4 C 0.02988(17) 0.83819(15) 0.09934(14) 0.0374(4) Uani 1 1 d . . . 
C5 C 0.13411(17) 0.76762(15) 0.07230(14) 0.0364(3) Uani 1 1 d . . . 
C6 C 0.25529(16) 0.72144(14) 0.14937(13) 0.0316(3) Uani 1 1 d . . . 
C7 C 0.26096(15) 0.37570(14) 0.61461(13) 0.0286(3) Uani 1 1 d . . . 
C8 C 0.34046(14) 0.59672(13) 0.47566(12) 0.0257(3) Uani 1 1 d . . . 
C9 C 0.39868(15) 0.69315(13) 0.34102(13) 0.0262(3) Uani 1 1 d . . . 
C10 C 0.51465(15) 0.79007(13) 0.34503(14) 0.0291(3) Uani 1 1 d . . . 
C11 C 0.61951(15) 0.71059(13) 0.30385(13) 0.0281(3) Uani 1 1 d . . . 
C12 C 0.52318(18) 0.92605(15) 0.23034(16) 0.0391(4) Uani 1 1 d . . . 
C13 C 0.61564(18) 0.92328(15) 0.14599(16) 0.0415(4) Uani 1 1 d . . . 
C15 C 0.34270(16) 0.32245(15) 0.28181(14) 0.0328(3) Uani 1 1 d . . . 
C16 C 0.46641(17) 0.36661(15) 0.20648(14) 0.0363(3) Uani 1 1 d . . . 
C17 C 0.48741(17) 0.34002(15) 0.10253(14) 0.0363(3) Uani 1 1 d . . . 
C18 C 0.38297(17) 0.27234(15) 0.07284(14) 0.0366(3) Uani 1 1 d . . . 
C19 C 0.25837(16) 0.22658(14) 0.14914(13) 0.0320(3) Uani 1 1 d . . . 
C20 C 0.23865(15) 0.25049(13) 0.25469(12) 0.0264(3) Uani 1 1 d . . . 
C21 C 0.23461(15) -0.12545(14) 0.61326(13) 0.0287(3) Uani 1 1 d . . . 
C22 C 0.16043(14) 0.09636(13) 0.47688(12) 0.0264(3) Uani 1 1 d . . . 
C23 C 0.10783(15) 0.19440(13) 0.34297(13) 0.0265(3) Uani 1 1 d . . . 
C24 C -0.00828(15) 0.29028(13) 0.34946(14) 0.0288(3) Uani 1 1 d . . . 
C25 C -0.11180(15) 0.21254(13) 0.30625(13) 0.0283(3) Uani 1 1 d . . . 
C26 C -0.01280(18) 0.42770(15) 0.23733(16) 0.0383(4) Uani 1 1 d . . . 
C27 C -0.10248(18) 0.42757(15) 0.15219(16) 0.0408(4) Uani 1 1 d . . . 
H1 H 0.1816(18) 0.8429(17) 0.3502(17) 0.041(4) Uiso 1 1 d . . . 
H2 H -0.026(2) 0.9150(18) 0.2198(16) 0.043(5) Uiso 1 1 d . . . 
H3 H -0.055(2) 0.8667(18) 0.0490(17) 0.046(5) Uiso 1 1 d . . . 
H4 H 0.1254(19) 0.7510(18) 0.0013(18) 0.046(5) Uiso 1 1 d . . . 
H5 H 0.3268(19) 0.6709(18) 0.1323(16) 0.041(4) Uiso 1 1 d . . . 
H6 H 0.1903(18) 0.3235(17) 0.5967(16) 0.037(4) Uiso 1 1 d . . . 
H7 H 0.2136(17) 0.4229(16) 0.6576(15) 0.032(4) Uiso 1 1 d . . . 
H8 H 0.5238(17) 0.7869(16) 0.4292(16) 0.035(4) Uiso 1 1 d . . . 
H9 H 0.470(2) 1.000(2) 0.2213(18) 0.048(5) Uiso 1 1 d . . . 
H10 H 0.648(2) 0.992(2) 0.0621(19) 0.056(5) Uiso 1 1 d . . . 
H11 H 0.3282(18) 0.3410(17) 0.3537(17) 0.042(4) Uiso 1 1 d . . . 
H12 H 0.539(2) 0.4142(18) 0.2254(17) 0.044(5) Uiso 1 1 d . . . 
H13 H 0.5743(18) 0.3691(16) 0.0517(16) 0.035(4) Uiso 1 1 d . . . 
H14 H 0.3968(18) 0.2572(17) -0.0006(17) 0.042(4) Uiso 1 1 d . . . 
H15 H 0.1858(18) 0.1781(17) 0.1304(16) 0.036(4) Uiso 1 1 d . . . 
H16 H 0.2821(17) -0.0811(16) 0.6568(15) 0.034(4) Uiso 1 1 d . . . 
H17 H 0.3055(17) -0.1770(16) 0.5933(14) 0.028(4) Uiso 1 1 d . . . 
H18 H -0.0233(17) 0.2848(16) 0.4335(16) 0.033(4) Uiso 1 1 d . . . 
H19 H 0.040(2) 0.502(2) 0.2299(18) 0.050(5) Uiso 1 1 d . . . 
H20 H -0.1330(19) 0.4981(19) 0.0701(18) 0.046(5) Uiso 1 1 d . . . 
O1 O 0.32143(10) 0.47262(9) 0.49090(9) 0.0275(2) Uani 1 1 d . . . 
O2 O 0.30863(12) 0.63276(10) 0.55471(9) 0.0352(3) Uani 1 1 d . . . 
O3 O 0.50466(10) 0.63193(9) 0.29216(9) 0.0281(2) Uani 1 1 d . . . 
O4 O 0.68189(11) 0.80064(10) 0.18197(9) 0.0369(3) Uani 1 1 d . . . 
O5 O 0.17902(10) -0.02725(9) 0.49043(9) 0.0280(2) Uani 1 1 d . . . 
O6 O 0.18931(12) 0.13090(10) 0.55690(9) 0.0358(3) Uani 1 1 d . . . 
O7 O 0.00359(10) 0.13500(9) 0.29247(9) 0.0290(2) Uani 1 1 d . . . 
O8 O -0.16953(12) 0.30516(11) 0.18525(9) 0.0375(3) Uani 1 1 d . . . 
  
  
_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 
C1 C6 1.3866(19) . ? 
C1 C2 1.395(2) . ? 
C1 C9 1.5140(19) . ? 
C2 C3 1.383(2) . ? 
C2 H1 0.980(17) . ? 
C3 C4 1.389(2) . ? 
C3 H2 0.939(18) . ? 
C4 C5 1.375(2) . ? 
C4 H3 0.956(19) . ? 
C5 C6 1.395(2) . ? 
C5 H4 0.935(18) . ? 
C6 H5 0.951(18) . ? 
C7 O1 1.4510(16) . ? 
C7 C11 1.503(2) 2_666 ? 
C7 H6 0.970(17) . ? 
C7 H7 0.984(16) . ? 
C8 O2 1.2009(16) . ? 
C8 O1 1.3383(16) . ? 
C8 C9 1.5271(18) . ? 
C9 O3 1.4542(16) . ? 
C9 C10 1.5528(18) . ? 
C10 C12 1.498(2) . ? 
C10 C11 1.5374(19) . ? 
C10 H8 0.971(17) . ? 
C11 O4 1.4228(16) . ? 
C11 O3 1.4369(16) . ? 
C11 C7 1.503(2) 2_666 ? 
C12 C13 1.307(3) . ? 
C12 H9 0.93(2) . ? 
C13 O4 1.391(2) . ? 
C13 H10 0.97(2) . ? 
C15 C16 1.379(2) . ? 
C15 C20 1.395(2) . ? 
C15 H11 0.962(18) . ? 
C16 C17 1.389(2) . ? 
C16 H12 0.954(18) . ? 
C17 C18 1.380(2) . ? 
C17 H13 0.957(17) . ? 
C18 C19 1.392(2) . ? 
C18 H14 0.956(17) . ? 
C19 C20 1.3874(19) . ? 
C19 H15 0.959(17) . ? 
C20 C23 1.5143(19) . ? 
C21 O5 1.4488(17) . ? 
C21 C25 1.503(2) 2_556 ? 
C21 H16 0.974(16) . ? 
C21 H17 0.972(16) . ? 
C22 O6 1.2012(16) . ? 
C22 O5 1.3395(16) . ? 
C22 C23 1.5249(19) . ? 
C23 O7 1.4569(15) . ? 
C23 C24 1.5516(19) . ? 
C24 C26 1.495(2) . ? 
C24 C25 1.5421(19) . ? 
C24 H18 0.961(16) . ? 
C25 O8 1.4243(17) . ? 
C25 O7 1.4355(16) . ? 
C25 C21 1.503(2) 2_556 ? 
C26 C27 1.308(3) . ? 
C26 H19 0.93(2) . ? 
C27 O8 1.3942(19) . ? 
C27 H20 0.966(19) . ? 
  
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 
C6 C1 C2 119.71(13) . . ? 
C6 C1 C9 120.08(12) . . ? 
C2 C1 C9 120.18(12) . . ? 
C3 C2 C1 120.20(14) . . ? 
C3 C2 H1 121.4(10) . . ? 
C1 C2 H1 118.4(10) . . ? 
C2 C3 C4 119.87(15) . . ? 
C2 C3 H2 120.6(11) . . ? 
C4 C3 H2 119.5(11) . . ? 
C5 C4 C3 120.12(14) . . ? 
C5 C4 H3 120.7(11) . . ? 
C3 C4 H3 119.2(11) . . ? 
C4 C5 C6 120.41(14) . . ? 
C4 C5 H4 120.5(11) . . ? 
C6 C5 H4 119.1(11) . . ? 
C1 C6 C5 119.65(14) . . ? 
C1 C6 H5 119.5(10) . . ? 
C5 C6 H5 120.8(10) . . ? 
O1 C7 C11 108.64(11) . 2_666 ? 
O1 C7 H6 106.9(10) . . ? 
C11 C7 H6 111.5(10) 2_666 . ? 
O1 C7 H7 109.5(9) . . ? 
C11 C7 H7 110.4(9) 2_666 . ? 
H6 C7 H7 109.7(13) . . ? 
O2 C8 O1 124.99(12) . . ? 
O2 C8 C9 122.38(12) . . ? 
O1 C8 C9 112.50(10) . . ? 
O3 C9 C1 112.63(10) . . ? 
O3 C9 C8 112.86(10) . . ? 
C1 C9 C8 107.73(11) . . ? 
O3 C9 C10 90.88(10) . . ? 
C1 C9 C10 119.82(11) . . ? 
C8 C9 C10 112.27(11) . . ? 
C12 C10 C11 101.53(12) . . ? 
C12 C10 C9 116.35(12) . . ? 
C11 C10 C9 84.60(9) . . ? 
C12 C10 H8 116.2(10) . . ? 
C11 C10 H8 119.8(10) . . ? 
C9 C10 H8 114.0(10) . . ? 
O4 C11 O3 112.48(10) . . ? 
O4 C11 C7 107.00(11) . 2_666 ? 
O3 C11 C7 111.77(11) . 2_666 ? 
O4 C11 C10 107.98(11) . . ? 
O3 C11 C10 92.17(10) . . ? 
C7 C11 C10 124.86(12) 2_666 . ? 
C13 C12 C10 109.04(14) . . ? 
C13 C12 H9 126.0(11) . . ? 
C10 C12 H9 124.9(11) . . ? 
C12 C13 O4 115.33(14) . . ? 
C12 C13 H10 131.9(12) . . ? 
O4 C13 H10 112.8(12) . . ? 
C16 C15 C20 120.38(13) . . ? 
C16 C15 H11 119.9(10) . . ? 
C20 C15 H11 119.8(10) . . ? 
C15 C16 C17 119.93(14) . . ? 
C15 C16 H12 121.1(11) . . ? 
C17 C16 H12 119.0(11) . . ? 
C18 C17 C16 119.98(14) . . ? 
C18 C17 H13 120.3(9) . . ? 
C16 C17 H13 119.7(9) . . ? 
C17 C18 C19 120.33(14) . . ? 
C17 C18 H14 119.4(10) . . ? 
C19 C18 H14 120.3(10) . . ? 
C20 C19 C18 119.75(14) . . ? 
C20 C19 H15 119.1(10) . . ? 
C18 C19 H15 121.1(10) . . ? 
C19 C20 C15 119.59(13) . . ? 
C19 C20 C23 120.28(12) . . ? 
C15 C20 C23 120.09(11) . . ? 
O5 C21 C25 108.51(11) . 2_556 ? 
O5 C21 H16 110.3(10) . . ? 
C25 C21 H16 111.5(9) 2_556 . ? 
O5 C21 H17 106.3(9) . . ? 
C25 C21 H17 111.3(9) 2_556 . ? 
H16 C21 H17 108.9(13) . . ? 
O6 C22 O5 124.95(13) . . ? 
O6 C22 C23 122.30(12) . . ? 
O5 C22 C23 112.61(10) . . ? 
O7 C23 C20 112.48(10) . . ? 
O7 C23 C22 112.97(10) . . ? 
C20 C23 C22 107.83(11) . . ? 
O7 C23 C24 90.89(10) . . ? 
C20 C23 C24 120.07(11) . . ? 
C22 C23 C24 111.94(11) . . ? 
C26 C24 C25 101.74(12) . . ? 
C26 C24 C23 116.66(11) . . ? 
C25 C24 C23 84.59(9) . . ? 
C26 C24 H18 115.9(10) . . ? 
C25 C24 H18 118.4(9) . . ? 
C23 C24 H18 115.0(10) . . ? 
O8 C25 O7 112.66(10) . . ? 
O8 C25 C21 106.96(12) . 2_556 ? 
O7 C25 C21 111.81(11) . 2_556 ? 
O8 C25 C24 107.74(11) . . ? 
O7 C25 C24 92.09(10) . . ? 
C21 C25 C24 125.01(11) 2_556 . ? 
C27 C26 C24 109.00(14) . . ? 
C27 C26 H19 125.7(12) . . ? 
C24 C26 H19 125.3(12) . . ? 
C26 C27 O8 115.35(14) . . ? 
C26 C27 H20 131.6(11) . . ? 
O8 C27 H20 113.1(11) . . ? 
C8 O1 C7 116.09(10) . . ? 
C11 O3 C9 92.00(9) . . ? 
C13 O4 C11 106.02(11) . . ? 
C22 O5 C21 116.16(10) . . ? 
C25 O7 C23 92.08(9) . . ? 
C27 O8 C25 106.08(11) . . ? 
  
_diffrn_measured_fraction_theta_max    0.977 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.977 
_refine_diff_density_max    0.216 
_refine_diff_density_min   -0.224 
_refine_diff_density_rms    0.039 
