# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 207/475
  
data_v7700 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C20 H16 O4' 
_chemical_formula_weight          320.33 
  
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                    7.4089(1) 
_cell_length_b                    10.5805(2) 
_cell_length_c                    20.2337(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.491(1) 
_cell_angle_gamma                 90.00 
_cell_volume                      1586.06(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     213(2) 
_cell_measurement_reflns_used     6727 
_cell_measurement_theta_min       2.2 
_cell_measurement_theta_max       26.2 
  
_exptl_crystal_description        irregular 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.40 
_exptl_crystal_size_mid           0.38 
_exptl_crystal_size_min           0.26 
_exptl_crystal_density_meas       no 
_exptl_crystal_density_diffrn     1.341 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              672 
_exptl_absorpt_coefficient_mu     0.093 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   0.9636 
_exptl_absorpt_correction_T_max   0.9761 
_exptl_absorpt_process_details    ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       213(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'long-fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             27860 
_diffrn_reflns_av_R_equivalents   0.039 
_diffrn_reflns_av_sigmaI/netI     0.0206 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -25 
_diffrn_reflns_limit_l_max        25 
_diffrn_reflns_theta_min          2.01 
_diffrn_reflns_theta_max          26.39 
_reflns_number_total              3243 
_reflns_number_gt                 2366 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXTL (Sheldrick, 1999)' 
_computing_structure_refinement   'SHELXTL (Sheldrick, 1999)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_refine_special_details 
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness 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 threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 
_refine_ls_weighting_details 
 'calc w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.3564P] 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     noref 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3243 
_refine_ls_number_parameters      245 
_refine_ls_number_restraints      3 
_refine_ls_R_factor_all           0.0603 
_refine_ls_R_factor_gt            0.0377 
_refine_ls_wR_factor_ref          0.1003 
_refine_ls_wR_factor_gt           0.0892 
_refine_ls_goodness_of_fit_ref    1.014 
_refine_ls_restrained_S_all       1.015 
_refine_ls_shift/su_max           0.000 
_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 0.60841(12) 0.87587(9) 0.13333(5) 0.0401(3) Uani 1 1 d . . . 
O2 O 0.73832(13) 1.02938(10) 0.07433(5) 0.0493(3) Uani 1 1 d . . . 
O3 O 0.45750(15) 1.19621(11) 0.01737(5) 0.0536(3) Uani 1 1 d . A . 
C1 C 0.42755(18) 0.84132(14) 0.15135(7) 0.0374(3) Uani 1 1 d . . . 
C2 C 0.40444(19) 0.81917(14) 0.22627(7) 0.0390(3) Uani 1 1 d . . . 
C3 C 0.3072(2) 0.69414(15) 0.23137(8) 0.0465(4) Uani 1 1 d . . . 
H3 H 0.3342 0.6374 0.2691 0.056 Uiso 1 1 calc R . . 
C4 C 0.2985(2) 0.64161(15) 0.16407(9) 0.0498(4) Uani 1 1 d . . . 
H4 H 0.2493 0.5620 0.1538 0.060 Uiso 1 1 calc R . . 
C5 C 0.36756(19) 0.71887(14) 0.11974(8) 0.0441(4) Uani 1 1 d . . . 
H5 H 0.3780 0.7002 0.0745 0.053 Uiso 1 1 calc R . . 
C6 C 0.60333(19) 0.98438(14) 0.09629(7) 0.0372(3) Uani 1 1 d . . . 
C7 C 0.41423(18) 1.02873(14) 0.09281(7) 0.0373(3) Uani 1 1 d . A . 
C8 C 0.31170(18) 0.94749(14) 0.12707(7) 0.0366(3) Uani 1 1 d . . . 
C9 C 0.12222(19) 0.94027(14) 0.14369(8) 0.0418(4) Uani 1 1 d . . . 
H9 H 0.0345 0.9801 0.1171 0.050 Uiso 1 1 calc R . . 
C10 C 0.07487(19) 0.87589(15) 0.19756(8) 0.0451(4) Uani 1 1 d . . . 
H10 H -0.0487 0.8657 0.2063 0.054 Uiso 1 1 calc R . . 
C11 C 0.20629(19) 0.82033(15) 0.24380(8) 0.0446(4) Uani 1 1 d . . . 
H11 H 0.1820 0.8382 0.2909 0.054 Uiso 1 1 calc R . . 
C12 C 0.54608(18) 0.86395(14) 0.27322(7) 0.0387(3) Uani 1 1 d . . . 
C13 C 0.5887(2) 0.99171(15) 0.27716(8) 0.0457(4) Uani 1 1 d . . . 
H13 H 0.5291 1.0494 0.2492 0.055 Uiso 1 1 calc R . . 
C14 C 0.7165(2) 1.03518(17) 0.32131(9) 0.0538(4) Uani 1 1 d . . . 
H14 H 0.7444 1.1218 0.3231 0.065 Uiso 1 1 calc R . . 
C15 C 0.8035(2) 0.95145(19) 0.36285(9) 0.0581(5) Uani 1 1 d . . . 
H15 H 0.8897 0.9810 0.3935 0.070 Uiso 1 1 calc R . . 
C16 C 0.7644(2) 0.82505(18) 0.35947(9) 0.0587(5) Uani 1 1 d . . . 
H16 H 0.8242 0.7680 0.3878 0.070 Uiso 1 1 calc R . . 
C17 C 0.6375(2) 0.78097(16) 0.31459(8) 0.0493(4) Uani 1 1 d . . . 
H17A H 0.6129 0.6939 0.3121 0.059 Uiso 1 1 calc R . . 
C18 C 0.3635(2) 1.14320(16) 0.05622(8) 0.0463(4) Uani 1 1 d D . . 
C19 C 0.1468(5) 1.3103(5) 0.04629(19) 0.0536(12) Uani 0.597(9) 1 d PD A 1 
H19A H 0.2484 1.3622 0.0316 0.064 Uiso 0.597(9) 1 calc PR A 1 
H19B H 0.0732 1.3611 0.0763 0.064 Uiso 0.597(9) 1 calc PR A 1 
C19' C 0.0982(10) 1.2460(6) 0.0117(4) 0.066(2) Uani 0.403(9) 1 d PD A 2 
H19C H -0.0325 1.2325 0.0087 0.079 Uiso 0.403(9) 1 calc PR A 2 
H19D H 0.1479 1.2321 -0.0325 0.079 Uiso 0.403(9) 1 calc PR A 2 
C20 C 0.0356(7) 1.2705(5) -0.0121(3) 0.0780(15) Uani 0.597(9) 1 d PD A 1 
H20A H -0.0093 1.3449 -0.0350 0.117 Uiso 0.597(9) 1 calc PR A 1 
H20B H -0.0654 1.2198 0.0026 0.117 Uiso 0.597(9) 1 calc PR A 1 
H20C H 0.1093 1.2211 -0.0419 0.117 Uiso 0.597(9) 1 calc PR A 1 
C20' C 0.1319(11) 1.3783(8) 0.0310(4) 0.093(3) Uani 0.403(9) 1 d PD A 2 
H20D H 0.0768 1.4344 -0.0013 0.139 Uiso 0.403(9) 1 calc PR A 2 
H20E H 0.2610 1.3936 0.0328 0.139 Uiso 0.403(9) 1 calc PR A 2 
H20F H 0.0803 1.3940 0.0741 0.139 Uiso 0.403(9) 1 calc PR A 2 
O4 O 0.2147(5) 1.1985(4) 0.0810(2) 0.0470(9) Uani 0.597(9) 1 d PD A 1 
O4' O 0.1748(6) 1.1526(6) 0.0565(3) 0.0518(13) Uani 0.403(9) 1 d PD A 2 
  
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 0.0295(5) 0.0452(6) 0.0455(6) 0.0062(5) 0.0022(4) 0.0051(4) 
O2 0.0338(5) 0.0542(7) 0.0600(7) 0.0084(5) 0.0061(5) -0.0026(5) 
O3 0.0527(7) 0.0594(7) 0.0487(7) 0.0132(6) 0.0035(5) 0.0014(5) 
C1 0.0285(7) 0.0405(8) 0.0433(8) 0.0012(6) 0.0020(6) 0.0019(6) 
C2 0.0341(7) 0.0393(8) 0.0436(8) 0.0036(6) 0.0033(6) 0.0003(6) 
C3 0.0422(8) 0.0421(9) 0.0552(10) 0.0062(7) 0.0031(7) -0.0036(7) 
C4 0.0464(9) 0.0375(9) 0.0654(11) -0.0035(8) 0.0022(8) -0.0014(7) 
C5 0.0390(8) 0.0433(9) 0.0501(9) -0.0058(7) 0.0023(7) 0.0057(7) 
C6 0.0339(7) 0.0406(8) 0.0369(7) -0.0010(6) -0.0007(6) 0.0013(6) 
C7 0.0342(7) 0.0416(8) 0.0361(7) -0.0019(6) -0.0012(6) 0.0027(6) 
C8 0.0325(7) 0.0414(8) 0.0359(7) -0.0048(6) -0.0032(6) 0.0029(6) 
C9 0.0303(7) 0.0441(9) 0.0509(9) -0.0048(7) -0.0036(6) 0.0036(6) 
C10 0.0297(7) 0.0478(9) 0.0580(10) -0.0059(7) 0.0054(7) -0.0018(6) 
C11 0.0371(8) 0.0495(9) 0.0472(9) -0.0004(7) 0.0072(7) -0.0042(7) 
C12 0.0322(7) 0.0450(9) 0.0392(8) 0.0037(6) 0.0044(6) 0.0019(6) 
C13 0.0409(8) 0.0455(9) 0.0507(9) 0.0054(7) -0.0022(7) 0.0021(7) 
C14 0.0496(9) 0.0505(10) 0.0611(10) -0.0011(8) -0.0026(8) -0.0086(8) 
C15 0.0459(9) 0.0756(13) 0.0527(10) 0.0044(9) -0.0096(8) -0.0104(9) 
C16 0.0490(10) 0.0659(12) 0.0609(11) 0.0170(9) -0.0106(8) -0.0003(8) 
C17 0.0448(9) 0.0480(9) 0.0551(10) 0.0100(8) -0.0014(7) 0.0009(7) 
C18 0.0443(9) 0.0535(10) 0.0411(8) 0.0067(7) 0.0013(7) 0.0081(7) 
C19 0.0530(19) 0.047(3) 0.060(2) 0.008(2) -0.0009(16) 0.0124(18) 
C19' 0.064(4) 0.069(4) 0.065(5) 0.005(4) -0.007(3) 0.024(3) 
C20 0.074(3) 0.083(3) 0.076(3) 0.010(2) -0.024(2) 0.016(2) 
C20' 0.120(6) 0.061(5) 0.098(5) 0.017(4) 0.034(4) 0.027(4) 
O4 0.0453(14) 0.0471(17) 0.0487(17) 0.0097(13) 0.0045(12) 0.0131(12) 
O4' 0.046(2) 0.050(3) 0.059(3) 0.008(2) -0.0041(18) 0.0112(18) 
  
_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 C6 1.3715(17) . ? 
O1 C1 1.4389(16) . ? 
O2 C6 1.1966(17) . ? 
O3 C18 1.1944(18) . ? 
C1 C8 1.4943(19) . ? 
C1 C5 1.510(2) . ? 
C1 C2 1.545(2) . ? 
C2 C12 1.487(2) . ? 
C2 C3 1.510(2) . ? 
C2 C11 1.513(2) . ? 
C3 C4 1.472(2) . ? 
C3 C11 1.552(2) . ? 
C4 C5 1.320(2) . ? 
C6 C7 1.4785(19) . ? 
C7 C8 1.344(2) . ? 
C7 C18 1.467(2) . ? 
C8 C9 1.448(2) . ? 
C9 C10 1.335(2) . ? 
C10 C11 1.467(2) . ? 
C12 C17 1.386(2) . ? 
C12 C13 1.390(2) . ? 
C13 C14 1.375(2) . ? 
C14 C15 1.378(2) . ? 
C15 C16 1.370(3) . ? 
C16 C17 1.383(2) . ? 
C18 O4 1.349(3) . ? 
C18 O4' 1.402(5) . ? 
C19 O4 1.462(5) . ? 
C19 C20 1.496(6) . ? 
C19' O4' 1.453(8) . ? 
C19' C20' 1.474(9) . ? 
  
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 O1 C1 109.26(10) . . ? 
O1 C1 C8 105.03(11) . . ? 
O1 C1 C5 112.45(11) . . ? 
C8 C1 C5 109.85(12) . . ? 
O1 C1 C2 113.48(11) . . ? 
C8 C1 C2 111.62(11) . . ? 
C5 C1 C2 104.52(12) . . ? 
C12 C2 C3 124.73(13) . . ? 
C12 C2 C11 121.89(13) . . ? 
C3 C2 C11 61.77(10) . . ? 
C12 C2 C1 119.67(12) . . ? 
C3 C2 C1 104.89(12) . . ? 
C11 C2 C1 110.17(12) . . ? 
C4 C3 C2 106.54(13) . . ? 
C4 C3 C11 117.22(14) . . ? 
C2 C3 C11 59.22(9) . . ? 
C5 C4 C3 112.38(14) . . ? 
C4 C5 C1 110.97(14) . . ? 
O2 C6 O1 121.12(13) . . ? 
O2 C6 C7 130.60(14) . . ? 
O1 C6 C7 108.25(12) . . ? 
C8 C7 C18 130.18(13) . . ? 
C8 C7 C6 108.19(13) . . ? 
C18 C7 C6 121.63(13) . . ? 
C7 C8 C9 134.99(14) . . ? 
C7 C8 C1 108.95(12) . . ? 
C9 C8 C1 116.05(13) . . ? 
C10 C9 C8 118.60(14) . . ? 
C9 C10 C11 123.19(13) . . ? 
C10 C11 C2 119.57(13) . . ? 
C10 C11 C3 124.01(14) . . ? 
C2 C11 C3 59.02(9) . . ? 
C17 C12 C13 118.15(14) . . ? 
C17 C12 C2 121.51(14) . . ? 
C13 C12 C2 120.34(13) . . ? 
C14 C13 C12 121.14(15) . . ? 
C15 C14 C13 119.82(16) . . ? 
C16 C15 C14 119.98(16) . . ? 
C15 C16 C17 120.29(16) . . ? 
C16 C17 C12 120.60(16) . . ? 
O3 C18 O4 121.58(18) . . ? 
O3 C18 O4' 123.8(2) . . ? 
O4 C18 O4' 31.66(17) . . ? 
O3 C18 C7 124.88(14) . . ? 
O4 C18 C7 112.18(16) . . ? 
O4' C18 C7 107.9(2) . . ? 
O4 C19 C20 109.7(6) . . ? 
O4' C19' C20' 114.6(11) . . ? 
C18 O4 C19 116.8(2) . . ? 
C18 O4' C19' 115.5(4) . . ? 
  
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              26.39 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.195 
_refine_diff_density_min   -0.154 
_refine_diff_density_rms    0.032