 
data_01sot020
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C23 H26 O8' 
_chemical_formula_weight          430.44 
 
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    P2(1)/n
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
 
_cell_length_a                    11.839(2) 
_cell_length_b                    8.0773(10) 
_cell_length_c                    22.695(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  91.84(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      2169.1(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     8063 
_cell_measurement_theta_min       1.02
_cell_measurement_theta_max       25.03 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.10 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.318 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              912 
_exptl_absorpt_coefficient_mu     0.100 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9901 
_exptl_absorpt_correction_T_max   0.9901 
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD' 
_diffrn_measurement_method        'Φ & ω scans'
_diffrn_detector_area_resol_mean  9.091 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             13956 
_diffrn_reflns_av_R_equivalents   0.3615 
_diffrn_reflns_av_sigmaI/netI     0.2909 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -8 
_diffrn_reflns_limit_k_max        8 
_diffrn_reflns_limit_l_min        -25 
_diffrn_reflns_limit_l_max        25 
_diffrn_reflns_theta_min          3.05 
_diffrn_reflns_theta_max          23.25 
_reflns_number_total              2999 
_reflns_number_gt                 947 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT (Hooft, 1998)' 
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' 
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' 
_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)+(0.1905P)²+0.0000P] 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      SHELXL 
_refine_ls_extinction_coef        0.005(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2999 
_refine_ls_number_parameters      281 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.2721 
_refine_ls_R_factor_gt            0.0864 
_refine_ls_wR_factor_ref          0.3345 
_refine_ls_wR_factor_gt           0.2145 
_refine_ls_goodness_of_fit_ref    0.811 
_refine_ls_restrained_S_all       0.811 
_refine_ls_shift/su_max           0.010 
_refine_ls_shift/su_mean          0.002 
 
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 0.0859(9) 0.3696(13) 0.0602(5) 0.079(3) Uani 1 1 d . . . 
H1A H 0.0236 0.3293 0.0346 0.118 Uiso 1 1 calc R . . 
H1B H 0.0581 0.3916 0.0997 0.118 Uiso 1 1 calc R . . 
H1C H 0.1456 0.2857 0.0628 0.118 Uiso 1 1 calc R . . 
C2 C 0.1774(15) 0.910(2) -0.0272(10) 0.199(11) Uani 1 1 d . . . 
H2A H 0.1214 0.8795 -0.0581 0.298 Uiso 1 1 calc R . . 
H2B H 0.2470 0.9464 -0.0454 0.298 Uiso 1 1 calc R . . 
H2C H 0.1474 0.9993 -0.0032 0.298 Uiso 1 1 calc R . . 
C3 C 0.4607(14) 1.0700(16) 0.0764(6) 0.150(7) Uani 1 1 d . . . 
H3A H 0.4704 1.1750 0.0555 0.225 Uiso 1 1 calc R . . 
H3B H 0.5283 1.0015 0.0723 0.225 Uiso 1 1 calc R . . 
H3C H 0.4493 1.0922 0.1183 0.225 Uiso 1 1 calc R . . 
C4 C 0.2729(7) 0.5250(12) 0.1148(4) 0.050(3) Uani 1 1 d . . . 
H4 H 0.2509 0.4188 0.1283 0.060 Uiso 1 1 calc R . . 
C5 C 0.2191(8) 0.5965(13) 0.0668(4) 0.056(3) Uani 1 1 d . . . 
C6 C 0.2495(11) 0.7514(15) 0.0457(5) 0.091(4) Uani 1 1 d . . . 
C7 C 0.3373(11) 0.8360(15) 0.0754(5) 0.078(4) Uani 1 1 d . . . 
C8 C 0.3924(8) 0.7692(13) 0.1245(5) 0.057(3) Uani 1 1 d . . . 
H8 H 0.4506 0.8288 0.1450 0.068 Uiso 1 1 calc R . . 
C9 C 0.3603(7) 0.6112(12) 0.1432(4) 0.049(3) Uani 1 1 d . . . 
C10 C 0.4171(7) 0.5431(11) 0.2002(4) 0.052(3) Uani 1 1 d . . . 
H10 H 0.4869 0.6079 0.2106 0.062 Uiso 1 1 calc R . . 
C11 C 0.4271(7) 0.2760(14) 0.2384(5) 0.049(3) Uani 1 1 d . . . 
C12 C 0.3704(7) 0.3793(12) 0.2854(4) 0.051(3) Uani 1 1 d . . . 
H12 H 0.3021 0.3219 0.3002 0.061 Uiso 1 1 calc R . . 
C13 C 0.4501(8) 0.4393(14) 0.3378(5) 0.059(3) Uani 1 1 d . . . 
H13 H 0.4069 0.4328 0.3749 0.071 Uiso 1 1 calc R . . 
C14 C 0.3720(8) 0.6745(13) 0.2974(4) 0.068(3) Uani 1 1 d . . . 
H14A H 0.3877 0.7803 0.2771 0.082 Uiso 1 1 calc R . . 
H14B H 0.3118 0.6928 0.3260 0.082 Uiso 1 1 calc R . . 
C15 C 0.3380(7) 0.5391(13) 0.2529(4) 0.054(3) Uani 1 1 d . . . 
H15 H 0.2562 0.5435 0.2406 0.065 Uiso 1 1 calc R . . 
C16 C 0.5580(8) 0.3500(12) 0.3478(4) 0.050(3) Uani 1 1 d . . . 
C17 C 0.5734(9) 0.2389(13) 0.3942(4) 0.061(3) Uani 1 1 d . . . 
H17 H 0.5131 0.2218 0.4202 0.073 Uiso 1 1 calc R . . 
C18 C 0.6743(8) 0.1513(12) 0.4042(5) 0.055(3) Uani 1 1 d . . . 
H18 H 0.6819 0.0751 0.4360 0.066 Uiso 1 1 calc R . . 
C19 C 0.7611(7) 0.1771(12) 0.3676(5) 0.054(3) Uani 1 1 d . . . 
C20 C 0.7496(8) 0.2892(13) 0.3197(4) 0.053(3) Uani 1 1 d . . . 
C21 C 0.6506(8) 0.3757(12) 0.3113(4) 0.053(3) Uani 1 1 d . . . 
H21 H 0.6443 0.4543 0.2802 0.063 Uiso 1 1 calc R . . 
C22 C 0.8290(8) 0.3968(13) 0.2333(5) 0.078(4) Uani 1 1 d . . . 
H22A H 0.8984 0.3933 0.2110 0.117 Uiso 1 1 calc R . . 
H22B H 0.8140 0.5111 0.2453 0.117 Uiso 1 1 calc R . . 
H22C H 0.7656 0.3560 0.2086 0.117 Uiso 1 1 calc R . . 
C23 C 0.8817(9) 0.0014(17) 0.4252(6) 0.120(6) Uani 1 1 d . . . 
H23A H 0.9574 -0.0475 0.4248 0.180 Uiso 1 1 calc R . . 
H23B H 0.8251 -0.0869 0.4264 0.180 Uiso 1 1 calc R . . 
H23C H 0.8755 0.0721 0.4601 0.180 Uiso 1 1 calc R . . 
O1 O 0.1307(6) 0.5206(9) 0.0360(3) 0.067(2) Uani 1 1 d . . . 
O2 O 0.1940(14) 0.8101(16) -0.0014(5) 0.225(9) Uani 1 1 d . . . 
O3 O 0.3652(9) 0.9851(11) 0.0520(3) 0.134(4) Uani 1 1 d . . . 
O4 O 0.4454(4) 0.3710(9) 0.1900(3) 0.0537(19) Uani 1 1 d . . . 
O5 O 0.4442(5) 0.1297(9) 0.2388(3) 0.0561(19) Uani 1 1 d . . . 
O6 O 0.4720(5) 0.6101(9) 0.3259(3) 0.065(2) Uani 1 1 d . . . 
O7 O 0.8423(5) 0.2937(8) 0.2851(3) 0.063(2) Uani 1 1 d . . . 
O8 O 0.8626(5) 0.0989(8) 0.3730(3) 0.075(2) 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 O1 1.446(11) . ? 
C2 O2 1.010(14) . ? 
C3 O3 1.420(13) . ? 
C4 C5 1.372(12) . ? 
C4 C9 1.388(12) . ? 
C5 O1 1.383(10) . ? 
C5 C6 1.391(13) . ? 
C6 O2 1.325(14) . ? 
C6 C7 1.399(14) . ? 
C7 O3 1.360(12) . ? 
C7 C8 1.383(13) . ? 
C8 C9 1.401(12) . ? 
C9 C10 1.540(13) . ? 
C10 O4 1.450(10) . ? 
C10 C15 1.542(13) . ? 
C11 O5 1.199(10) . ? 
C11 O4 1.363(11) . ? 
C11 C12 1.526(13) . ? 
C12 C15 1.530(13) . ? 
C12 C13 1.571(12) . ? 
C13 O6 1.431(10) . ? 
C13 C16 1.478(12) . ? 
C14 O6 1.430(10) . ? 
C14 C15 1.534(12) . ? 
C16 C17 1.392(12) . ? 
C16 C21 1.410(12) . ? 
C17 C18 1.401(12) . ? 
C18 C19 1.358(12) . ? 
C19 O8 1.360(10) . ? 
C19 C20 1.417(12) . ? 
C20 O7 1.371(10) . ? 
C20 C21 1.373(12) . ? 
C22 O7 1.446(10) . ? 
C23 O8 1.434(11) . ? 
 
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 
C5 C4 C9 118.6(10) . . ? 
C4 C5 O1 122.7(9) . . ? 
C4 C5 C6 122.2(10) . . ? 
O1 C5 C6 115.2(9) . . ? 
O2 C6 C5 118.2(11) . . ? 
O2 C6 C7 123.7(11) . . ? 
C5 C6 C7 118.1(11) . . ? 
O3 C7 C8 123.1(11) . . ? 
O3 C7 C6 115.5(11) . . ? 
C8 C7 C6 121.4(11) . . ? 
C7 C8 C9 118.3(10) . . ? 
C4 C9 C8 121.4(10) . . ? 
C4 C9 C10 120.7(9) . . ? 
C8 C9 C10 117.7(9) . . ? 
O4 C10 C9 107.7(8) . . ? 
O4 C10 C15 104.7(7) . . ? 
C9 C10 C15 113.4(8) . . ? 
O5 C11 O4 122.0(10) . . ? 
O5 C11 C12 127.7(10) . . ? 
O4 C11 C12 109.9(9) . . ? 
C11 C12 C15 103.5(8) . . ? 
C11 C12 C13 115.5(7) . . ? 
C15 C12 C13 103.9(8) . . ? 
O6 C13 C16 109.8(8) . . ? 
O6 C13 C12 105.2(8) . . ? 
C16 C13 C12 117.4(9) . . ? 
O6 C14 C15 103.6(7) . . ? 
C12 C15 C14 103.2(8) . . ? 
C12 C15 C10 104.0(7) . . ? 
C14 C15 C10 110.0(8) . . ? 
C17 C16 C21 117.0(9) . . ? 
C17 C16 C13 121.5(9) . . ? 
C21 C16 C13 121.5(10) . . ? 
C16 C17 C18 122.5(10) . . ? 
C19 C18 C17 118.8(10) . . ? 
C18 C19 O8 123.8(10) . . ? 
C18 C19 C20 120.7(9) . . ? 
O8 C19 C20 115.4(9) . . ? 
O7 C20 C21 127.1(10) . . ? 
O7 C20 C19 113.4(9) . . ? 
C21 C20 C19 119.5(9) . . ? 
C20 C21 C16 121.3(10) . . ? 
C5 O1 C1 117.6(7) . . ? 
C2 O2 C6 146.7(17) . . ? 
C7 O3 C3 118.4(10) . . ? 
C11 O4 C10 111.5(8) . . ? 
C14 O6 C13 106.5(8) . . ? 
C20 O7 C22 114.4(7) . . ? 
C19 O8 C23 116.4(8) . . ? 
 
_diffrn_measured_fraction_theta_max    0.967 
_diffrn_reflns_theta_full              23.25 
_diffrn_measured_fraction_theta_full   0.967 
_refine_diff_density_max    0.397 
_refine_diff_density_min   -0.275 
_refine_diff_density_rms    0.065 
