# Copyright The Royal Society of Chemistry, 1999
# CCDC Number: 207/293

#  Perkin 1. Paper 8/08884E 

# Goesta Brunow


data_se 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          'C24 H28 O10' 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C24 H28 O10' 
_chemical_formula_weight          476.46 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
 
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    'P 1 21/c 1'
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    9.133(2) 
_cell_length_b                    10.921(2) 
_cell_length_c                    22.979(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  91.29(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      2291.4(8) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     193(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           0.40 
_exptl_crystal_size_mid           0.37 
_exptl_crystal_size_min           0.32
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.381 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              1008 
_exptl_absorpt_coefficient_mu     0.108 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       193(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        'Rigaku AFC7S diffractometer' 
_diffrn_measurement_method        2\q/\w                            
_diffrn_standards_number          3 
_diffrn_standards_interval_count  200 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             3165 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.1019 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        27 
_diffrn_reflns_theta_min          2.57 
_diffrn_reflns_theta_max          25.01 
_reflns_number_total              3165 
_reflns_number_observed           1774 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        TEXSAN 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXTL/PC (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 39 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses 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 observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0863P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     ? 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3126 
_refine_ls_number_parameters      314 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1433 
_refine_ls_R_factor_obs           0.0762 
_refine_ls_wR_factor_all          0.2004 
_refine_ls_wR_factor_obs          0.1651 
_refine_ls_goodness_of_fit_all    1.027 
_refine_ls_goodness_of_fit_obs    1.243 
_refine_ls_restrained_S_all       1.093 
_refine_ls_restrained_S_obs       1.243 
_refine_ls_shift/esd_max          0.100 
_refine_ls_shift/esd_mean         0.005 
 
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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
O1 O 0.0445(5) 0.1803(4) 0.1314(2) 0.0638(13) Uani 1 d . . 
O2 O 0.4778(4) -0.1344(3) 0.1144(2) 0.0442(10) Uani 1 d . . 
O3 O 0.6124(4) -0.1048(4) 0.2164(2) 0.0568(12) Uani 1 d . . 
O4 O 0.4977(4) 0.0113(4) 0.30594(15) 0.0445(10) Uani 1 d . . 
O5 O 0.4390(5) 0.2935(5) 0.0762(2) 0.083(2) Uani 1 d . . 
O6 O 0.5435(5) 0.2330(4) 0.1587(2) 0.0574(12) Uani 1 d . . 
O7 O 0.1046(4) 0.7133(3) 0.1732(2) 0.0522(11) Uani 1 d . . 
O8 O -0.1238(4) 0.7381(3) 0.0993(2) 0.0417(10) Uani 1 d . . 
O9 O 0.0346(5) 0.8036(4) 0.0338(2) 0.0586(12) Uani 1 d . . 
O10 O -0.2144(4) 0.5570(3) 0.0325(2) 0.0429(10) Uani 1 d . . 
C1 C 0.0850(6) 0.1272(6) 0.1841(3) 0.058(2) Uani 1 d . . 
H1A H 0.0592(6) 0.1836(6) 0.2142(3) 0.070 Uiso 1 d R . 
C2 C 0.2608(7) 0.1237(5) 0.1817(3) 0.051(2) Uani 1 d . . 
C3 C 0.3102(6) 0.0286(5) 0.1387(2) 0.045(2) Uani 1 d . . 
H3A H 0.2583(6) 0.0214(5) 0.1021(2) 0.055 Uiso 1 d R . 
C4 C 0.4219(6) -0.0472(5) 0.1501(2) 0.0382(14) Uani 1 d . . 
C5 C 0.5019(6) -0.0467(5) 0.2075(2) 0.0378(14) Uani 1 d . . 
C6 C 0.4354(6) 0.0315(4) 0.2527(2) 0.0345(13) Uani 1 d . . 
C7 C 0.3287(6) 0.1095(5) 0.2407(2) 0.045(2) Uani 1 d . . 
H7A H 0.2926(6) 0.1596(5) 0.2715(2) 0.054 Uiso 1 d R . 
C8 C 0.2835(7) 0.2502(5) 0.1557(3) 0.052(2) Uani 1 d . . 
H8A H 0.2783(7) 0.3092(5) 0.1865(3) 0.062 Uiso 1 d R . 
C9 C 0.1563(6) 0.2747(5) 0.1137(2) 0.0440(15) Uani 1 d . . 
H9A H 0.1882(6) 0.2557(5) 0.0752(2) 0.053 Uiso 1 d R . 
C10 C 0.0864(6) 0.4007(4) 0.1128(2) 0.0339(13) Uani 1 d . . 
C11 C 0.1356(6) 0.4982(5) 0.1467(2) 0.0375(14) Uani 1 d . . 
H11A H 0.2166(6) 0.4875(5) 0.1736(2) 0.045 Uiso 1 d R . 
C12 C 0.0680(6) 0.6110(4) 0.1418(2) 0.0352(13) Uani 1 d . . 
C13 C -0.0485(6) 0.6264(5) 0.1033(2) 0.0346(13) Uani 1 d . . 
C14 C -0.0999(6) 0.5284(5) 0.0690(2) 0.0333(13) Uani 1 d . . 
C15 C -0.0327(5) 0.4162(5) 0.0744(2) 0.0357(13) Uani 1 d . . 
H15A H -0.0684(5) 0.3483(5) 0.0517(2) 0.043 Uiso 1 d R . 
C16 C 0.0132(7) 0.0115(6) 0.1964(3) 0.056(2) Uani 1 d . . 
H16A H -0.0932(7) 0.0232(9) 0.1955(16) 0.084 Uiso 1 calc R . 
H16B H 0.0447(32) -0.0176(18) 0.2351(7) 0.084 Uiso 1 calc R . 
H16C H 0.0396(33) -0.0491(11) 0.1670(10) 0.084 Uiso 1 calc R . 
C17 C 0.4107(7) -0.1479(6) 0.0579(2) 0.057(2) Uani 1 d . . 
H17A H 0.4637(26) -0.2099(26) 0.0358(6) 0.085 Uiso 1 calc R . 
H17B H 0.4137(38) -0.0695(11) 0.0372(7) 0.085 Uiso 1 calc R . 
H17C H 0.3086(14) -0.1736(34) 0.0619(2) 0.085 Uiso 1 calc R . 
C18 C 0.4300(7) 0.0718(5) 0.3541(2) 0.051(2) Uani 1 d . . 
H18A H 0.4765(28) 0.0443(26) 0.3906(3) 0.077 Uiso 1 calc R . 
H18B H 0.3255(11) 0.0517(27) 0.3541(10) 0.077 Uiso 1 calc R . 
H18C H 0.4421(35) 0.1606(6) 0.3502(9) 0.077 Uiso 1 calc R . 
C19 C 0.4290(6) 0.2627(5) 0.1270(3) 0.0435(15) Uani 1 d . . 
C20 C 0.6833(7) 0.2328(7) 0.1333(3) 0.072(2) Uani 1 d . . 
H20A H 0.7552(12) 0.1970(39) 0.1606(8) 0.108 Uiso 1 calc R . 
H20B H 0.7118(23) 0.3171(7) 0.1242(18) 0.108 Uiso 1 calc R . 
H20C H 0.6795(14) 0.1843(35) 0.0974(11) 0.108 Uiso 1 calc R . 
C21 C 0.2308(7) 0.7085(5) 0.2106(2) 0.050(2) Uani 1 d . . 
H21A H 0.2380(23) 0.7844(15) 0.2332(12) 0.075 Uiso 1 calc R . 
H21B H 0.3185(8) 0.6992(33) 0.1872(3) 0.075 Uiso 1 calc R . 
H21C H 0.2229(19) 0.6386(20) 0.2371(11) 0.075 Uiso 1 calc R . 
C22 C -0.0759(7) 0.8198(5) 0.0594(3) 0.044(2) Uani 1 d . . 
C23 C -0.1784(7) 0.9256(6) 0.0539(3) 0.072(2) Uani 1 d . . 
H23A H -0.1273(15) 0.9955(13) 0.0369(18) 0.108 Uiso 1 calc R . 
H23B H -0.2133(38) 0.9480(26) 0.0925(4) 0.108 Uiso 1 calc R . 
H23C H -0.2620(25) 0.9029(14) 0.0287(16) 0.108 Uiso 1 calc R . 
C24 C -0.2760(6) 0.4601(5) -0.0017(2) 0.0429(15) Uani 1 d . . 
H24A H -0.3449(28) 0.4940(6) -0.0308(10) 0.064 Uiso 1 calc R . 
H24B H -0.3277(31) 0.4031(17) 0.0236(3) 0.064 Uiso 1 calc R . 
H24C H -0.1976(7) 0.4164(19) -0.0215(11) 0.064 Uiso 1 calc R . 
 
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 0.058(3) 0.055(3) 0.078(3) 0.008(2) -0.013(2) 0.007(2) 
O2 0.055(3) 0.038(2) 0.039(2) -0.004(2) -0.005(2) 0.010(2) 
O3 0.051(3) 0.071(3) 0.048(3) 0.000(2) -0.010(2) 0.033(2) 
O4 0.045(2) 0.051(2) 0.037(2) 0.000(2) -0.004(2) -0.001(2) 
O5 0.087(4) 0.094(4) 0.065(3) 0.034(3) -0.022(3) 0.000(3) 
O6 0.045(3) 0.052(3) 0.074(3) 0.013(2) -0.013(2) 0.001(2) 
O7 0.055(3) 0.036(2) 0.065(3) -0.015(2) -0.025(2) 0.011(2) 
O8 0.043(2) 0.036(2) 0.046(2) 0.001(2) -0.003(2) 0.014(2) 
O9 0.060(3) 0.044(3) 0.072(3) 0.009(2) 0.011(3) 0.007(2) 
O10 0.043(2) 0.041(2) 0.044(2) 0.003(2) -0.017(2) 0.010(2) 
C1 0.037(4) 0.050(4) 0.088(5) -0.001(4) -0.002(3) 0.009(3) 
C2 0.061(4) 0.044(4) 0.049(4) -0.005(3) -0.011(3) 0.013(3) 
C3 0.050(4) 0.036(3) 0.050(4) -0.004(3) -0.020(3) 0.010(3) 
C4 0.047(4) 0.032(3) 0.036(3) 0.001(3) -0.008(3) -0.006(3) 
C5 0.043(3) 0.035(3) 0.035(3) 0.012(3) -0.006(3) -0.004(3) 
C6 0.043(3) 0.026(3) 0.035(3) 0.005(2) -0.009(3) -0.003(3) 
C7 0.058(4) 0.037(3) 0.039(3) -0.001(3) -0.014(3) 0.007(3) 
C8 0.066(5) 0.042(4) 0.046(4) 0.002(3) -0.007(3) 0.009(3) 
C9 0.047(4) 0.035(3) 0.049(4) -0.002(3) -0.013(3) -0.006(3) 
C10 0.040(3) 0.021(3) 0.041(3) 0.004(2) -0.007(3) 0.003(2) 
C11 0.045(3) 0.033(3) 0.035(3) 0.005(3) -0.009(3) 0.005(3) 
C12 0.039(3) 0.024(3) 0.042(3) -0.001(2) -0.002(3) -0.001(3) 
C13 0.036(3) 0.027(3) 0.041(3) 0.008(3) -0.003(3) 0.005(2) 
C14 0.041(3) 0.027(3) 0.032(3) 0.007(2) -0.004(3) 0.003(3) 
C15 0.036(3) 0.033(3) 0.038(3) -0.001(2) -0.008(3) -0.005(3) 
C16 0.053(4) 0.063(4) 0.053(4) 0.016(3) 0.010(3) 0.025(4) 
C17 0.068(4) 0.051(4) 0.051(4) -0.014(3) -0.016(3) 0.001(3) 
C18 0.060(4) 0.054(4) 0.040(3) 0.001(3) 0.000(3) 0.006(3) 
C19 0.038(4) 0.030(3) 0.062(4) 0.005(3) -0.009(3) 0.004(3) 
C20 0.043(4) 0.078(5) 0.095(5) 0.008(4) 0.000(4) -0.001(4) 
C21 0.067(4) 0.033(3) 0.050(4) -0.003(3) -0.016(3) -0.010(3) 
C22 0.053(4) 0.030(3) 0.049(4) 0.008(3) -0.014(3) 0.001(3) 
C23 0.079(5) 0.048(4) 0.088(5) 0.021(4) -0.010(4) 0.028(4) 
C24 0.041(3) 0.047(4) 0.041(3) 0.007(3) -0.009(3) -0.007(3) 
 
_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 1.385(7) . ? 
O1 C9 1.514(7) . ? 
O2 C4 1.364(6) . ? 
O2 C17 1.431(6) . ? 
O3 C5 1.206(6) . ? 
O4 C6 1.355(6) . ? 
O4 C18 1.440(6) . ? 
O5 C19 1.222(7) . ? 
O6 C19 1.301(6) . ? 
O6 C20 1.416(7) . ? 
O7 C12 1.368(6) . ? 
O7 C21 1.422(6) . ? 
O8 C22 1.358(7) . ? 
O8 C13 1.402(6) . ? 
O9 C22 1.193(7) . ? 
O10 C14 1.363(6) . ? 
O10 C24 1.427(6) . ? 
C1 C16 1.454(8) . ? 
C1 C2 1.608(8) . ? 
C2 C7 1.486(7) . ? 
C2 C3 1.509(8) . ? 
C2 C8 1.521(8) . ? 
C3 C4 1.335(7) . ? 
C4 C5 1.493(7) . ? 
C5 C6 1.485(7) . ? 
C6 C7 1.319(7) . ? 
C8 C19 1.503(9) . ? 
C8 C9 1.517(7) . ? 
C9 C10 1.517(7) . ? 
C10 C15 1.395(7) . ? 
C10 C11 1.388(7) . ? 
C11 C12 1.382(7) . ? 
C12 C13 1.379(7) . ? 
C13 C14 1.402(7) . ? 
C14 C15 1.375(7) . ? 
C22 C23 1.491(8) . ? 
 
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 O1 C9 110.6(4) . . ? 
C4 O2 C17 117.4(4) . . ? 
C6 O4 C18 116.1(4) . . ? 
C19 O6 C20 119.3(5) . . ? 
C12 O7 C21 118.3(4) . . ? 
C22 O8 C13 116.8(4) . . ? 
C14 O10 C24 117.2(4) . . ? 
O1 C1 C16 114.9(5) . . ? 
O1 C1 C2 103.1(5) . . ? 
C16 C1 C2 116.2(5) . . ? 
C7 C2 C3 113.6(5) . . ? 
C7 C2 C8 113.3(5) . . ? 
C3 C2 C8 108.8(5) . . ? 
C7 C2 C1 111.5(5) . . ? 
C3 C2 C1 110.7(5) . . ? 
C8 C2 C1 97.9(5) . . ? 
C4 C3 C2 122.5(5) . . ? 
C3 C4 O2 127.5(5) . . ? 
C3 C4 C5 121.8(5) . . ? 
O2 C4 C5 110.6(5) . . ? 
O3 C5 C6 122.5(5) . . ? 
O3 C5 C4 122.6(5) . . ? 
C6 C5 C4 114.8(5) . . ? 
C7 C6 O4 126.0(5) . . ? 
C7 C6 C5 122.4(5) . . ? 
O4 C6 C5 111.6(4) . . ? 
C6 C7 C2 123.4(5) . . ? 
C19 C8 C9 112.2(5) . . ? 
C19 C8 C2 112.6(5) . . ? 
C9 C8 C2 107.5(5) . . ? 
O1 C9 C8 102.7(4) . . ? 
O1 C9 C10 109.6(4) . . ? 
C8 C9 C10 119.0(4) . . ? 
C15 C10 C11 120.0(5) . . ? 
C15 C10 C9 116.2(4) . . ? 
C11 C10 C9 123.9(5) . . ? 
C12 C11 C10 119.9(5) . . ? 
O7 C12 C13 114.5(4) . . ? 
O7 C12 C11 125.5(5) . . ? 
C13 C12 C11 119.9(5) . . ? 
C12 C13 C14 120.7(5) . . ? 
C12 C13 O8 121.2(5) . . ? 
C14 C13 O8 118.0(4) . . ? 
O10 C14 C15 126.4(5) . . ? 
O10 C14 C13 114.4(4) . . ? 
C15 C14 C13 119.1(5) . . ? 
C14 C15 C10 120.4(5) . . ? 
O5 C19 O6 121.8(6) . . ? 
O5 C19 C8 122.0(5) . . ? 
O6 C19 C8 116.1(5) . . ? 
O9 C22 O8 121.6(5) . . ? 
O9 C22 C23 127.6(6) . . ? 
O8 C22 C23 110.8(6) . . ? 
 
_refine_diff_density_max    0.617 
_refine_diff_density_min   -0.250 
_refine_diff_density_rms    0.061 


# END OF CIF