 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C26 H30 O9'
_chemical_formula_weight          486.50
 
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   0.0000
 '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   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    P212121
_symmetry_Space_group_name_hall   'P 2ac 2ab'
 
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                    8.3420(17)
_cell_length_b                    12.846(3)
_cell_length_c                    22.736(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2436.3(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     15872
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       30.4
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.15
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.326
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1032
_exptl_absorpt_coefficient_mu     0.100
_exptl_absorpt_correction_type    Empirical
_exptl_absorpt_correction_T_min   0.9610
_exptl_absorpt_correction_T_max   0.9851
_exptl_absorpt_process_details    'SORTAV (R. H. Blessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'π and θ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             15872
_diffrn_reflns_av_R_equivalents   0.0485
_diffrn_reflns_av_sigmaI/netI     0.0443
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -31
_diffrn_reflns_limit_l_max        31
_diffrn_reflns_theta_min          2.91
_diffrn_reflns_theta_max          30.40
_reflns_number_total              3625
_reflns_number_gt                 2868
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   'PLATON (Spek, 1990)'
 
_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 > 2σ(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)+(0.0618P)²+0.0054P] where P=(Fo²+2Fc²)/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        0
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns          3625
_refine_ls_number_parameters      322
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0658
_refine_ls_R_factor_gt            0.0427
_refine_ls_wR_factor_ref          0.1050
_refine_ls_wR_factor_gt           0.0957
_refine_ls_goodness_of_fit_ref    1.090
_refine_ls_restrained_S_all       1.090
_refine_ls_shift/su_max           0.007
_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 0.2231(2) 0.79233(12) -0.12277(7) 0.0408(4) Uani 1 1 d . . .
O2 O 0.03053(19) 0.65349(11) -0.07981(7) 0.0344(3) Uani 1 1 d . . .
O3 O 0.56287(19) 0.26168(10) -0.02465(6) 0.0317(3) Uani 1 1 d . . .
O4 O 0.1172(2) 0.54945(12) 0.26772(7) 0.0431(4) Uani 1 1 d . . .
O5 O 0.2129(2) 0.71391(12) 0.21371(6) 0.0406(4) Uani 1 1 d . . .
O6 O 0.40256(18) 0.25553(10) 0.16814(6) 0.0307(3) Uani 1 1 d . . .
O7 O 0.2771(2) 0.11382(12) 0.13315(7) 0.0466(4) Uani 1 1 d . . .
O8 O 0.63300(17) 0.33945(10) 0.09384(6) 0.0268(3) Uani 1 1 d . . .
O9 O 0.6985(2) 0.17401(12) 0.11975(7) 0.0431(4) Uani 1 1 d . . .
C1 C 0.3230(4) 0.8729(2) -0.14448(14) 0.0604(8) Uani 1 1 d . . .
H1A H 0.3693 0.9115 -0.1114 0.091 Uiso 1 1 calc R . .
H1B H 0.2595 0.9204 -0.1689 0.091 Uiso 1 1 calc R . .
H1C H 0.4094 0.8427 -0.1682 0.091 Uiso 1 1 calc R . .
C2 C -0.0752(3) 0.57622(19) -0.05729(12) 0.0452(6) Uani 1 1 d . . .
H2A H -0.0309 0.5070 -0.0652 0.068 Uiso 1 1 calc R . .
H2B H -0.1800 0.5828 -0.0764 0.068 Uiso 1 1 calc R . .
H2C H -0.0876 0.5857 -0.0148 0.068 Uiso 1 1 calc R . .
C3 C 0.2892(3) 0.72656(15) -0.08181(8) 0.0287(4) Uani 1 1 d . . .
C4 C 0.1837(2) 0.65245(15) -0.05803(8) 0.0263(4) Uani 1 1 d . . .
C5 C 0.2364(2) 0.58528(15) -0.01445(8) 0.0252(4) Uani 1 1 d . . .
H5 H 0.1637 0.5367 0.0023 0.030 Uiso 1 1 calc R . .
C6 C 0.3959(2) 0.58809(14) 0.00518(8) 0.0237(4) Uani 1 1 d . . .
C7 C 0.4988(2) 0.65973(15) -0.01951(9) 0.0276(4) Uani 1 1 d . . .
H7 H 0.6072 0.6621 -0.0068 0.033 Uiso 1 1 calc R . .
C8 C 0.4464(3) 0.72893(15) -0.06287(8) 0.0304(4) Uani 1 1 d . . .
H8 H 0.5192 0.7778 -0.0794 0.037 Uiso 1 1 calc R . .
C9 C 0.4522(2) 0.50920(14) 0.05041(8) 0.0244(4) Uani 1 1 d . . .
H9 H 0.5684 0.5222 0.0584 0.029 Uiso 1 1 calc R . .
C10 C 0.4354(2) 0.39981(14) 0.02551(8) 0.0230(4) Uani 1 1 d . . .
H10 H 0.3209 0.3903 0.0137 0.028 Uiso 1 1 calc R . .
C11 C 0.5388(3) 0.37288(15) -0.02756(9) 0.0293(4) Uani 1 1 d . . .
H11A H 0.4836 0.3923 -0.0645 0.035 Uiso 1 1 calc R . .
H11B H 0.6426 0.4100 -0.0257 0.035 Uiso 1 1 calc R . .
C12 C 0.4819(3) 0.22211(15) 0.02661(9) 0.0283(4) Uani 1 1 d . . .
H12A H 0.5417 0.1630 0.0439 0.034 Uiso 1 1 calc R . .
H12B H 0.3722 0.1986 0.0166 0.034 Uiso 1 1 calc R . .
C13 C 0.4766(2) 0.31331(15) 0.06906(8) 0.0249(4) Uani 1 1 d . . .
C14 C 0.3501(2) 0.31573(15) 0.11782(8) 0.0243(4) Uani 1 1 d . . .
H14 H 0.2480 0.2854 0.1024 0.029 Uiso 1 1 calc R . .
C15 C 0.3180(2) 0.42568(15) 0.13961(8) 0.0251(4) Uani 1 1 d . . .
C16 C 0.2347(3) 0.43564(16) 0.19335(8) 0.0285(4) Uani 1 1 d . . .
H16 H 0.2034 0.3748 0.2141 0.034 Uiso 1 1 calc R . .
C17 C 0.1982(3) 0.53201(16) 0.21617(8) 0.0301(4) Uani 1 1 d . . .
C18 C 0.1032(4) 0.4643(2) 0.30721(11) 0.0587(8) Uani 1 1 d . . .
H18A H 0.0368 0.4099 0.2893 0.088 Uiso 1 1 calc R . .
H18B H 0.0531 0.4880 0.3438 0.088 Uiso 1 1 calc R . .
H18C H 0.2099 0.4363 0.3157 0.088 Uiso 1 1 calc R . .
C19 C 0.2477(3) 0.62202(15) 0.18615(9) 0.0300(5) Uani 1 1 d . . .
C20 C 0.2875(4) 0.80486(18) 0.19096(12) 0.0580(8) Uani 1 1 d . . .
H20A H 0.4026 0.7922 0.1862 0.087 Uiso 1 1 calc R . .
H20B H 0.2711 0.8629 0.2183 0.087 Uiso 1 1 calc R . .
H20C H 0.2403 0.8222 0.1527 0.087 Uiso 1 1 calc R . .
C21 C 0.3272(3) 0.61290(16) 0.13294(9) 0.0277(4) Uani 1 1 d . . .
H21 H 0.3586 0.6739 0.1123 0.033 Uiso 1 1 calc R . .
C22 C 0.3621(2) 0.51459(15) 0.10894(8) 0.0250(4) Uani 1 1 d . . .
C23 C 0.3620(3) 0.15415(16) 0.16927(9) 0.0326(5) Uani 1 1 d . . .
C24 C 0.4400(4) 0.1004(2) 0.21972(11) 0.0501(6) Uani 1 1 d . . .
H24A H 0.3804 0.0367 0.2291 0.075 Uiso 1 1 calc R . .
H24B H 0.4404 0.1466 0.2540 0.075 Uiso 1 1 calc R . .
H24C H 0.5505 0.0823 0.2092 0.075 Uiso 1 1 calc R . .
C25 C 0.7269(3) 0.26508(16) 0.11949(9) 0.0310(5) Uani 1 1 d . . .
C26 C 0.8723(3) 0.31354(19) 0.14630(10) 0.0386(5) Uani 1 1 d . . .
H26A H 0.9233 0.2637 0.1730 0.058 Uiso 1 1 calc R . .
H26B H 0.8411 0.3759 0.1683 0.058 Uiso 1 1 calc R . .
H26C H 0.9480 0.3328 0.1152 0.058 Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.373(2) . ?
O1 C1 1.418(3) . ?
O2 C4 1.370(3) . ?
O2 C2 1.423(3) . ?
O3 C12 1.440(2) . ?
O3 C11 1.444(2) . ?
O4 C17 1.371(2) . ?
O4 C18 1.420(3) . ?
O5 C19 1.368(2) . ?
O5 C20 1.421(3) . ?
O6 C23 1.346(3) . ?
O6 C14 1.449(2) . ?
O7 C23 1.202(3) . ?
O8 C25 1.366(2) . ?
O8 C13 1.460(2) . ?
O9 C25 1.194(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C8 1.381(3) . ?
C3 C4 1.405(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.404(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(3) . ?
C6 C9 1.518(3) . ?
C7 C8 1.398(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.521(3) . ?
C9 C22 1.530(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.523(3) . ?
C10 C13 1.527(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.519(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.531(3) . ?
C14 C15 1.521(3) . ?
C14 H14 1.0000 . ?
C15 C22 1.388(3) . ?
C15 C16 1.411(3) . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C17 C19 1.405(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C21 1.384(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.406(3) . ?
C21 H21 0.9500 . ?
C23 C24 1.489(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.493(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
 
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
C3 O1 C1 116.73(19) . . ?
C4 O2 C2 116.18(17) . . ?
C12 O3 C11 108.72(14) . . ?
C17 O4 C18 117.08(17) . . ?
C19 O5 C20 116.74(17) . . ?
C23 O6 C14 117.11(16) . . ?
C25 O8 C13 121.08(15) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 C8 125.39(19) . . ?
O1 C3 C4 115.26(19) . . ?
C8 C3 C4 119.34(18) . . ?
O2 C4 C5 124.07(19) . . ?
O2 C4 C3 116.00(17) . . ?
C5 C4 C3 119.91(19) . . ?
C4 C5 C6 120.80(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 118.56(18) . . ?
C7 C6 C9 121.93(18) . . ?
C5 C6 C9 119.44(17) . . ?
C6 C7 C8 121.16(19) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 120.19(19) . . ?
C3 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C6 C9 C10 109.63(14) . . ?
C6 C9 C22 114.00(16) . . ?
C10 C9 C22 108.68(15) . . ?
C6 C9 H9 108.1 . . ?
C10 C9 H9 108.1 . . ?
C22 C9 H9 108.1 . . ?
C9 C10 C11 116.92(16) . . ?
C9 C10 C13 114.20(15) . . ?
C11 C10 C13 102.78(15) . . ?
C9 C10 H10 107.5 . . ?
C11 C10 H10 107.5 . . ?
C13 C10 H10 107.5 . . ?
O3 C11 C10 105.51(15) . . ?
O3 C11 H11A 110.6 . . ?
C10 C11 H11A 110.6 . . ?
O3 C11 H11B 110.6 . . ?
C10 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?
O3 C12 C13 104.82(15) . . ?
O3 C12 H12A 110.8 . . ?
C13 C12 H12A 110.8 . . ?
O3 C12 H12B 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
O8 C13 C12 113.37(16) . . ?
O8 C13 C10 106.48(14) . . ?
C12 C13 C10 98.96(14) . . ?
O8 C13 C14 109.37(14) . . ?
C12 C13 C14 119.74(17) . . ?
C10 C13 C14 107.44(16) . . ?
O6 C14 C15 106.97(14) . . ?
O6 C14 C13 110.67(16) . . ?
C15 C14 C13 112.12(16) . . ?
O6 C14 H14 109.0 . . ?
C15 C14 H14 109.0 . . ?
C13 C14 H14 109.0 . . ?
C22 C15 C16 119.40(18) . . ?
C22 C15 C14 123.64(16) . . ?
C16 C15 C14 116.94(16) . . ?
C17 C16 C15 121.12(18) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
O4 C17 C16 125.32(18) . . ?
O4 C17 C19 115.20(17) . . ?
C16 C17 C19 119.47(17) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 C21 125.10(18) . . ?
O5 C19 C17 115.17(17) . . ?
C21 C19 C17 119.72(18) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 C22 120.94(18) . . ?
C19 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C15 C22 C21 119.29(17) . . ?
C15 C22 C9 122.01(17) . . ?
C21 C22 C9 118.67(17) . . ?
O7 C23 O6 123.5(2) . . ?
O7 C23 C24 125.7(2) . . ?
O6 C23 C24 110.7(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O9 C25 O8 125.0(2) . . ?
O9 C25 C26 124.6(2) . . ?
O8 C25 C26 110.39(18) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.878
_diffrn_reflns_theta_full              30.40
_diffrn_measured_fraction_theta_full   0.878
_refine_diff_density_max    0.186
_refine_diff_density_min   -0.234
_refine_diff_density_rms    0.051
