data_01sot001
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C29 H27 O8'
_chemical_formula_weight          503.51
 
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    C2/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    37.557(7)
_cell_length_b                    7.0816(14)
_cell_length_c                    22.498(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  124.86(3)
_cell_angle_gamma                 90.00
_cell_volume                      4909.9(16)
_cell_formula_units_Z             8
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     16139
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       23.53
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.48
_exptl_crystal_size_mid           0.07
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.362
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              2120
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9538
_exptl_absorpt_correction_T_max   0.9990
_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          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             18113
_diffrn_reflns_av_R_equivalents   0.1666
_diffrn_reflns_av_sigmaI/netI     0.0997
_diffrn_reflns_limit_h_min        -42
_diffrn_reflns_limit_h_max        42
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          23.61
_reflns_number_total              3642
_reflns_number_gt                 2251
_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     'CAMERON (Watkin, Pearce 1995)'
_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)+(0.0627P)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     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0019(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3642
_refine_ls_number_parameters      442
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0946
_refine_ls_R_factor_gt            0.0527
_refine_ls_wR_factor_ref          0.1481
_refine_ls_wR_factor_gt           0.1220
_refine_ls_goodness_of_fit_ref    1.011
_refine_ls_restrained_S_all       1.011
_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 0.33850(13) 0.8414(5) 0.1315(2) 0.0424(9) Uani 1 1 d . . .
C2 C 0.34335(10) 0.9533(4) 0.23485(15) 0.0314(7) Uani 1 1 d . . .
C3 C 0.31925(9) 0.9927(4) 0.26761(14) 0.0268(7) Uani 1 1 d . . .
C4 C 0.34302(10) 1.0389(4) 0.34103(15) 0.0277(7) Uani 1 1 d . . .
C5 C 0.32153(9) 1.0802(4) 0.37270(14) 0.0267(7) Uani 1 1 d . . .
C6 C 0.34488(10) 1.1377(4) 0.45050(14) 0.0292(7) Uani 1 1 d . . .
C7 C 0.41302(13) 1.1704(6) 0.56249(16) 0.0443(9) Uani 1 1 d . . .
C8 C 0.27641(10) 1.0754(4) 0.33196(15) 0.0280(7) Uani 1 1 d . . .
C9 C 0.25190(9) 1.0276(4) 0.25802(14) 0.0265(7) Uani 1 1 d . . .
C10 C 0.27431(9) 0.9894(4) 0.22715(15) 0.0284(7) Uani 1 1 d . . .
C11 C 0.20367(9) 1.0244(4) 0.21519(14) 0.0271(7) Uani 1 1 d . . .
C12 C 0.18215(9) 0.9779(4) 0.24687(15) 0.0285(7) Uani 1 1 d . . .
C13 C 0.13682(9) 0.9779(4) 0.20660(14) 0.0285(7) Uani 1 1 d . . .
C14 C 0.11293(10) 0.9323(4) 0.23935(15) 0.0329(7) Uani 1 1 d . . .
C15 C 0.11867(13) 0.8514(6) 0.34632(19) 0.0466(9) Uani 1 1 d . . .
C16 C 0.11261(11) 1.0236(4) 0.13341(15) 0.0301(7) Uani 1 1 d . . .
C17 C 0.13372(9) 1.0696(4) 0.10097(14) 0.0284(7) Uani 1 1 d . . .
C18 C 0.10931(10) 1.1270(4) 0.02343(15) 0.0316(7) Uani 1 1 d . . .
C19 C 0.03967(12) 1.1579(6) -0.08656(17) 0.0462(9) Uani 1 1 d . . .
C20 C 0.17860(10) 1.0708(4) 0.14144(15) 0.0286(7) Uani 1 1 d . . .
C41 C 0.02442(13) 0.4903(8) 0.2332(2) 0.0680(14) Uani 1 1 d . . .
C42 C 0.02429(17) 0.2999(9) 0.2335(2) 0.0851(18) Uani 1 1 d . . .
C43 C 0.0000 0.2056(9) 0.2500 0.101(3) Uani 1 2 d S . .
H43 H 0.0000 0.0714 0.2500 0.122 Uiso 1 2 calc SR . .
C46 C 0.0000 0.5856(8) 0.2500 0.0647(19) Uani 1 2 d S . .
C47 C 0.02532(13) 0.4071(6) 0.06563(19) 0.0542(10) Uani 1 1 d . . .
C48 C -0.00793(13) 0.3137(5) 0.0049(2) 0.0559(10) Uani 1 1 d . . .
C49 C 0.03294(12) 0.5926(6) 0.0603(2) 0.0561(10) Uani 1 1 d . . .
C53 C 0.22795(12) 0.2878(5) 0.03085(17) 0.0451(9) Uani 1 1 d . . .
C54 C 0.22907(11) 0.1050(5) 0.00972(17) 0.0434(9) Uani 1 1 d . . .
C55 C 0.24901(11) 0.4311(5) 0.02140(17) 0.0435(8) Uani 1 1 d . . .
O1 O 0.31812(7) 0.8772(3) 0.16853(10) 0.0374(6) Uani 1 1 d . . .
O2 O 0.38157(7) 0.9838(3) 0.26444(11) 0.0467(6) Uani 1 1 d . . .
O3 O 0.32699(7) 1.1884(3) 0.47805(10) 0.0414(6) Uani 1 1 d . . .
O4 O 0.38786(7) 1.1263(3) 0.48526(10) 0.0375(6) Uani 1 1 d . . .
O5 O 0.07384(7) 0.9327(3) 0.20671(11) 0.0408(6) Uani 1 1 d . . .
O6 O 0.13971(7) 0.8915(3) 0.31015(10) 0.0392(6) Uani 1 1 d . . .
O7 O 0.12573(7) 1.1907(3) -0.00503(11) 0.0456(6) Uani 1 1 d . . .
O8 O 0.06665(7) 1.0959(3) -0.01136(10) 0.0388(6) Uani 1 1 d . . .
H1A H 0.3409(12) 0.958(5) 0.110(2) 0.072(12) Uiso 1 1 d . . .
H1B H 0.3187(12) 0.754(5) 0.092(2) 0.070(11) Uiso 1 1 d . . .
H1C H 0.3676(14) 0.785(5) 0.163(2) 0.078(13) Uiso 1 1 d . . .
H4 H 0.3741(9) 1.035(3) 0.3687(14) 0.025(7) Uiso 1 1 d . . .
H7A H 0.4026(13) 1.305(6) 0.570(2) 0.090(13) Uiso 1 1 d . . .
H7B H 0.4453(14) 1.175(5) 0.578(2) 0.075(12) Uiso 1 1 d . . .
H7C H 0.4067(11) 1.072(5) 0.5851(18) 0.060(11) Uiso 1 1 d . . .
H8 H 0.2611(9) 1.100(4) 0.3563(15) 0.034(8) Uiso 1 1 d . . .
H10 H 0.2582(10) 0.964(4) 0.1761(16) 0.042(8) Uiso 1 1 d . . .
H12 H 0.1979(8) 0.947(3) 0.2965(14) 0.021(7) Uiso 1 1 d . . .
H15A H 0.0976(13) 0.960(5) 0.338(2) 0.076(13) Uiso 1 1 d . . .
H15B H 0.1444(12) 0.827(5) 0.401(2) 0.067(11) Uiso 1 1 d . . .
H15C H 0.0996(12) 0.733(5) 0.3227(18) 0.066(11) Uiso 1 1 d . . .
H16 H 0.0832(10) 1.028(4) 0.1094(15) 0.031(8) Uiso 1 1 d . . .
H19A H 0.0389(14) 1.308(7) -0.085(2) 0.102(15) Uiso 1 1 d . . .
H19B H 0.0093(13) 1.114(5) -0.1077(19) 0.064(11) Uiso 1 1 d . . .
H19C H 0.0507(11) 1.107(5) -0.1126(18) 0.056(10) Uiso 1 1 d . . .
H20 H 0.1941(9) 1.102(3) 0.1193(14) 0.025(7) Uiso 1 1 d . . .
H41 H 0.0410(16) 0.552(6) 0.220(2) 0.109(17) Uiso 1 1 d . . .
H42 H 0.0403(17) 0.233(7) 0.216(3) 0.127(18) Uiso 1 1 d . . .
H46 H 0.0000 0.715(8) 0.2500 0.066(16) Uiso 1 2 d S . .
H47 H 0.0443(13) 0.337(5) 0.115(2) 0.074(11) Uiso 1 1 d . . .
H48 H -0.0135(13) 0.185(6) 0.012(2) 0.081(13) Uiso 1 1 d . . .
H49 H 0.0565(15) 0.659(6) 0.106(2) 0.102(15) Uiso 1 1 d . . .
H53 H 0.2108(10) 0.315(4) 0.0520(16) 0.048(9) Uiso 1 1 d . . .
H54 H 0.2150(11) 0.010(5) 0.0172(19) 0.062(11) Uiso 1 1 d . . .
H55 H 0.2478(11) 0.561(5) 0.0362(18) 0.059(10) Uiso 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 1.440(4) . ?
C2 O2 1.207(3) . ?
C2 O1 1.341(3) . ?
C2 C3 1.484(4) . ?
C3 C10 1.386(4) . ?
C3 C4 1.395(4) . ?
C4 C5 1.379(4) . ?
C5 C8 1.392(4) . ?
C5 C6 1.498(4) . ?
C6 O3 1.200(3) . ?
C6 O4 1.334(3) . ?
C7 O4 1.460(4) . ?
C8 C9 1.407(4) . ?
C9 C10 1.390(4) . ?
C9 C11 1.488(4) . ?
C11 C12 1.389(4) . ?
C11 C20 1.401(4) . ?
C12 C13 1.399(4) . ?
C13 C16 1.390(4) . ?
C13 C14 1.486(4) . ?
C14 O5 1.209(3) . ?
C14 O6 1.342(3) . ?
C15 O6 1.450(4) . ?
C16 C17 1.389(4) . ?
C17 C20 1.384(4) . ?
C17 C18 1.490(4) . ?
C18 O7 1.202(3) . ?
C18 O8 1.340(4) . ?
C19 O8 1.457(4) . ?
C41 C42 1.348(7) . ?
C41 C46 1.356(5) . ?
C42 C43 1.342(7) . ?
C43 C42 1.342(7) 2 ?
C46 C41 1.356(5) 2 ?
C47 C49 1.364(5) . ?
C47 C48 1.383(5) . ?
C48 C49 1.378(5) 5_565 ?
C49 C48 1.378(5) 5_565 ?
C53 C55 1.376(5) . ?
C53 C54 1.388(5) . ?
C54 C55 1.375(5) 7 ?
C55 C54 1.375(5) 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
O2 C2 O1 123.1(3) . . ?
O2 C2 C3 124.2(3) . . ?
O1 C2 C3 112.6(3) . . ?
C10 C3 C4 119.7(3) . . ?
C10 C3 C2 122.0(2) . . ?
C4 C3 C2 118.2(3) . . ?
C5 C4 C3 119.6(3) . . ?
C4 C5 C8 120.4(3) . . ?
C4 C5 C6 122.4(3) . . ?
C8 C5 C6 117.1(3) . . ?
O3 C6 O4 124.2(3) . . ?
O3 C6 C5 123.9(3) . . ?
O4 C6 C5 111.9(3) . . ?
C5 C8 C9 120.8(3) . . ?
C10 C9 C8 117.6(3) . . ?
C10 C9 C11 122.3(2) . . ?
C8 C9 C11 120.1(3) . . ?
C3 C10 C9 121.8(3) . . ?
C12 C11 C20 118.0(3) . . ?
C12 C11 C9 121.4(2) . . ?
C20 C11 C9 120.6(3) . . ?
C11 C12 C13 121.2(3) . . ?
C16 C13 C12 119.8(3) . . ?
C16 C13 C14 117.8(3) . . ?
C12 C13 C14 122.4(3) . . ?
O5 C14 O6 123.2(3) . . ?
O5 C14 C13 124.5(3) . . ?
O6 C14 C13 112.3(3) . . ?
C17 C16 C13 119.6(3) . . ?
C20 C17 C16 120.2(3) . . ?
C20 C17 C18 118.1(3) . . ?
C16 C17 C18 121.7(3) . . ?
O7 C18 O8 123.8(3) . . ?
O7 C18 C17 124.5(3) . . ?
O8 C18 C17 111.7(3) . . ?
C17 C20 C11 121.3(3) . . ?
C42 C41 C46 119.4(5) . . ?
C43 C42 C41 120.3(5) . . ?
C42 C43 C42 120.4(6) 2 . ?
C41 C46 C41 120.3(6) 2 . ?
C49 C47 C48 119.3(3) . . ?
C49 C48 C47 120.2(4) 5_565 . ?
C47 C49 C48 120.5(4) . 5_565 ?
C55 C53 C54 120.2(3) . . ?
C55 C54 C53 119.5(3) 7 . ?
C54 C55 C53 120.4(3) 7 . ?
C2 O1 C1 116.3(3) . . ?
C6 O4 C7 115.3(3) . . ?
C14 O6 C15 115.4(3) . . ?
C18 O8 C19 115.8(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              23.61
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.235
_refine_diff_density_min   -0.263
_refine_diff_density_rms    0.055
