# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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data_cd2663
_database_code_depnum_ccdc_archive 'CCDC 648596'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 O6'
_chemical_formula_weight         394.41

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7495(7)
_cell_length_b                   10.1805(9)
_cell_length_c                   13.3793(12)
_cell_angle_alpha                93.494(2)
_cell_angle_beta                 91.931(2)
_cell_angle_gamma                109.458(2)
_cell_volume                     991.77(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2143
_cell_measurement_theta_min      5.426
_cell_measurement_theta_max      55.782

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.75789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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_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            5856
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4188
_reflns_number_gt                2969
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0851P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4188
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1539
_refine_ls_wR_factor_gt          0.1429
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
O1 O 0.02012(17) -0.08327(15) 0.34462(9) 0.0642(4) Uani 1 1 d . . .
O2 O 0.30925(15) -0.02094(12) 0.40509(8) 0.0461(3) Uani 1 1 d . . .
O3 O 0.57543(17) 0.32002(14) 0.40962(9) 0.0568(4) Uani 1 1 d . . .
O4 O 0.27268(17) 0.24937(12) 0.42578(9) 0.0525(3) Uani 1 1 d . . .
O5 O 0.3915(3) 0.5694(2) 0.13012(15) 0.1009(8) Uani 1 1 d . . .
O6 O 0.3401(2) 0.51237(18) 0.28417(12) 0.0825(5) Uani 1 1 d . . .
C1 C 0.3511(3) 0.0783(2) -0.11341(13) 0.0529(5) Uani 1 1 d . . .
H1 H 0.4359 0.1681 -0.1035 0.063 Uiso 1 1 calc R . .
C2 C 0.3113(3) 0.0135(2) -0.20839(14) 0.0631(5) Uani 1 1 d . . .
H2 H 0.3702 0.0596 -0.2621 0.076 Uiso 1 1 calc R . .
C3 C 0.1843(3) -0.1199(2) -0.22532(14) 0.0671(6) Uani 1 1 d . . .
H3 H 0.1566 -0.1623 -0.2902 0.081 Uiso 1 1 calc R . .
C4 C 0.1005(3) -0.1885(2) -0.14699(14) 0.0592(5) Uani 1 1 d . . .
H4 H 0.0147 -0.2777 -0.1588 0.071 Uiso 1 1 calc R . .
C5 C 0.1412(2) -0.12684(18) -0.04809(12) 0.0451(4) Uani 1 1 d . . .
C6 C 0.2655(2) 0.01053(18) -0.03091(11) 0.0404(4) Uani 1 1 d . . .
C7 C 0.2995(2) 0.07529(16) 0.07134(11) 0.0375(4) Uani 1 1 d . . .
C8 C 0.2171(2) -0.00234(16) 0.15149(11) 0.0371(4) Uani 1 1 d . . .
C9 C 0.0966(2) -0.14353(18) 0.12971(13) 0.0480(4) Uani 1 1 d . . .
H9 H 0.0433 -0.1962 0.1820 0.058 Uiso 1 1 calc R . .
C10 C 0.0599(3) -0.20047(19) 0.03500(14) 0.0542(5) Uani 1 1 d . . .
H10 H -0.0215 -0.2913 0.0232 0.065 Uiso 1 1 calc R . .
C11 C 0.2590(2) 0.06183(16) 0.25059(11) 0.0365(4) Uani 1 1 d . . .
C12 C 0.3734(2) 0.19927(16) 0.26903(11) 0.0363(4) Uani 1 1 d . . .
C13 C 0.4476(2) 0.27927(16) 0.18814(12) 0.0388(4) Uani 1 1 d . . .
C14 C 0.4096(2) 0.21556(17) 0.09241(12) 0.0413(4) Uani 1 1 d . . .
H14 H 0.4592 0.2678 0.0393 0.050 Uiso 1 1 calc R . .
C15 C 0.1792(2) -0.02184(17) 0.33656(12) 0.0403(4) Uani 1 1 d . . .
C16 C 0.2427(3) -0.0842(2) 0.49718(13) 0.0594(5) Uani 1 1 d . . .
H16A H 0.1630 -0.0395 0.5263 0.089 Uiso 1 1 calc R . .
H16B H 0.3447 -0.0729 0.5436 0.089 Uiso 1 1 calc R . .
H16C H 0.1763 -0.1819 0.4824 0.089 Uiso 1 1 calc R . .
C17 C 0.4213(2) 0.26298(17) 0.37458(12) 0.0416(4) Uani 1 1 d . . .
C18 C 0.3079(3) 0.3028(2) 0.52996(15) 0.0758(7) Uani 1 1 d . . .
H18A H 0.3933 0.2661 0.5615 0.114 Uiso 1 1 calc R . .
H18B H 0.1953 0.2748 0.5635 0.114 Uiso 1 1 calc R . .
H18C H 0.3585 0.4029 0.5339 0.114 Uiso 1 1 calc R . .
C19 C 0.5571(2) 0.43522(18) 0.20436(14) 0.0478(4) Uani 1 1 d . . .
C20 C 0.7043(3) 0.4879(2) 0.12968(17) 0.0734(6) Uani 1 1 d . . .
H20A H 0.6471 0.4847 0.0644 0.110 Uiso 1 1 calc R . .
H20B H 0.7797 0.4298 0.1273 0.110 Uiso 1 1 calc R . .
H20C H 0.7787 0.5824 0.1503 0.110 Uiso 1 1 calc R . .
C21 C 0.4240(3) 0.51452(19) 0.20125(15) 0.0584(5) Uani 1 1 d . . .
C22 C 0.2044(4) 0.5826(4) 0.2888(3) 0.1104(10) Uani 1 1 d . . .
H22A H 0.2651 0.6819 0.3050 0.122 Uiso 1 1 calc R . .
H22B H 0.1384 0.5699 0.2240 0.122 Uiso 1 1 calc R . .
C23 C 0.0797(4) 0.5264(4) 0.3629(3) 0.1114(12) Uani 1 1 d . . .
H23A H 0.0212 0.4278 0.3471 0.132 Uiso 1 1 calc R . .
H23B H -0.0114 0.5712 0.3647 0.132 Uiso 1 1 calc R . .
H23C H 0.1448 0.5420 0.4273 0.132 Uiso 1 1 calc R . .
H19 H 0.615(2) 0.4513(19) 0.2721(14) 0.052(5) Uiso 1 1 d . . .

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 0.0417(7) 0.0846(10) 0.0510(8) 0.0261(7) 0.0050(6) -0.0028(6)
O2 0.0453(7) 0.0534(7) 0.0390(6) 0.0153(5) 0.0015(5) 0.0139(5)
O3 0.0493(8) 0.0625(8) 0.0478(7) 0.0011(6) -0.0044(6) 0.0058(6)
O4 0.0551(7) 0.0491(7) 0.0470(7) -0.0029(6) 0.0157(6) 0.0091(6)
O5 0.186(2) 0.1266(17) 0.0912(14) 0.0420(12) 0.0128(13) 0.1013(17)
O6 0.0998(12) 0.0909(12) 0.0773(10) 0.0167(9) 0.0203(9) 0.0561(10)
C1 0.0602(11) 0.0590(11) 0.0405(9) 0.0078(8) 0.0088(8) 0.0203(9)
C2 0.0764(14) 0.0766(14) 0.0394(10) 0.0105(9) 0.0122(9) 0.0281(12)
C3 0.0834(15) 0.0806(16) 0.0395(10) -0.0073(10) 0.0001(10) 0.0327(13)
C4 0.0675(13) 0.0574(12) 0.0502(11) -0.0071(9) -0.0025(9) 0.0203(10)
C5 0.0479(9) 0.0468(10) 0.0426(9) 0.0013(7) 0.0017(7) 0.0190(8)
C6 0.0426(9) 0.0457(10) 0.0373(8) 0.0068(7) 0.0045(7) 0.0198(8)
C7 0.0384(8) 0.0400(9) 0.0367(8) 0.0078(7) 0.0039(6) 0.0157(7)
C8 0.0359(8) 0.0377(8) 0.0375(8) 0.0077(7) 0.0038(6) 0.0112(7)
C9 0.0533(10) 0.0412(9) 0.0443(9) 0.0101(7) 0.0064(8) 0.0073(8)
C10 0.0571(11) 0.0421(10) 0.0536(11) 0.0017(8) 0.0022(9) 0.0039(8)
C11 0.0344(8) 0.0398(9) 0.0367(8) 0.0102(7) 0.0055(6) 0.0127(7)
C12 0.0346(8) 0.0383(9) 0.0362(8) 0.0066(6) 0.0039(6) 0.0118(7)
C13 0.0372(8) 0.0362(8) 0.0416(8) 0.0082(7) 0.0047(7) 0.0091(7)
C14 0.0435(9) 0.0424(9) 0.0377(8) 0.0138(7) 0.0103(7) 0.0115(7)
C15 0.0427(9) 0.0392(9) 0.0361(8) 0.0077(7) 0.0044(7) 0.0091(7)
C16 0.0654(12) 0.0669(13) 0.0435(10) 0.0238(9) 0.0034(9) 0.0155(10)
C17 0.0474(10) 0.0346(8) 0.0412(9) 0.0080(7) 0.0061(7) 0.0105(7)
C18 0.0916(16) 0.0664(14) 0.0525(12) -0.0119(10) 0.0262(11) 0.0047(12)
C19 0.0522(10) 0.0373(9) 0.0459(10) 0.0084(7) 0.0013(8) 0.0036(8)
C20 0.0653(13) 0.0583(13) 0.0762(14) 0.0126(11) 0.0159(11) -0.0087(10)
C21 0.0773(13) 0.0356(10) 0.0580(11) 0.0086(8) -0.0014(10) 0.0128(9)
C22 0.113(2) 0.108(2) 0.136(3) -0.003(2) 0.007(2) 0.073(2)
C23 0.090(2) 0.125(3) 0.154(3) -0.030(2) 0.020(2) 0.0478(19)

_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 C15 1.1942(19) . ?
O2 C15 1.3367(19) . ?
O2 C16 1.455(2) . ?
O3 C17 1.205(2) . ?
O4 C17 1.331(2) . ?
O4 C18 1.448(2) . ?
O5 C21 1.193(2) . ?
O6 C21 1.302(2) . ?
O6 C22 1.457(3) . ?
C1 C2 1.371(3) . ?
C1 C6 1.404(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.356(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.408(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(2) . ?
C5 C10 1.424(2) . ?
C6 C7 1.458(2) . ?
C7 C14 1.404(2) . ?
C7 C8 1.413(2) . ?
C8 C11 1.419(2) . ?
C8 C9 1.435(2) . ?
C9 C10 1.341(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.386(2) . ?
C11 C15 1.499(2) . ?
C12 C13 1.415(2) . ?
C12 C17 1.498(2) . ?
C13 C14 1.376(2) . ?
C13 C19 1.528(2) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C21 1.508(3) . ?
C19 C20 1.524(3) . ?
C19 H19 0.977(18) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 C23 1.419(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C15 O2 C16 115.29(13) . . ?
C17 O4 C18 115.28(14) . . ?
C21 O6 C22 117.5(2) . . ?
C2 C1 C6 120.79(18) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.77(18) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.78(17) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.11(19) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 119.29(17) . . ?
C4 C5 C10 121.45(17) . . ?
C6 C5 C10 119.26(15) . . ?
C1 C6 C5 118.19(15) . . ?
C1 C6 C7 123.19(15) . . ?
C5 C6 C7 118.62(14) . . ?
C14 C7 C8 118.55(14) . . ?
C14 C7 C6 121.43(14) . . ?
C8 C7 C6 120.00(14) . . ?
C7 C8 C11 118.62(14) . . ?
C7 C8 C9 118.76(14) . . ?
C11 C8 C9 122.61(14) . . ?
C10 C9 C8 120.87(16) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C5 122.36(16) . . ?
C9 C10 H10 118.8 . . ?
C5 C10 H10 118.8 . . ?
C12 C11 C8 121.23(14) . . ?
C12 C11 C15 119.74(13) . . ?
C8 C11 C15 119.02(13) . . ?
C11 C12 C13 120.01(14) . . ?
C11 C12 C17 120.20(13) . . ?
C13 C12 C17 119.78(13) . . ?
C14 C13 C12 118.46(14) . . ?
C14 C13 C19 119.86(14) . . ?
C12 C13 C19 121.57(14) . . ?
C13 C14 C7 122.99(14) . . ?
C13 C14 H14 118.5 . . ?
C7 C14 H14 118.5 . . ?
O1 C15 O2 122.86(15) . . ?
O1 C15 C11 125.52(15) . . ?
O2 C15 C11 111.62(13) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O4 123.57(15) . . ?
O3 C17 C12 124.42(15) . . ?
O4 C17 C12 112.01(14) . . ?
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 . . ?
C21 C19 C20 110.56(17) . . ?
C21 C19 C13 108.12(14) . . ?
C20 C19 C13 114.28(15) . . ?
C21 C19 H19 107.6(10) . . ?
C20 C19 H19 109.0(11) . . ?
C13 C19 H19 107.0(11) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 O6 122.5(2) . . ?
O5 C21 C19 124.7(2) . . ?
O6 C21 C19 112.67(17) . . ?
C23 C22 O6 109.6(3) . . ?
C23 C22 H22A 109.7 . . ?
O6 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
O6 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 2.7(3) . . . . ?
C3 C4 C5 C10 -177.19(18) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C1 C6 C7 -178.64(16) . . . . ?
C4 C5 C6 C1 -3.2(2) . . . . ?
C10 C5 C6 C1 176.70(15) . . . . ?
C4 C5 C6 C7 177.07(15) . . . . ?
C10 C5 C6 C7 -3.1(2) . . . . ?
C1 C6 C7 C14 5.6(2) . . . . ?
C5 C6 C7 C14 -174.62(15) . . . . ?
C1 C6 C7 C8 -176.01(15) . . . . ?
C5 C6 C7 C8 3.7(2) . . . . ?
C14 C7 C8 C11 -4.2(2) . . . . ?
C6 C7 C8 C11 177.37(13) . . . . ?
C14 C7 C8 C9 176.74(14) . . . . ?
C6 C7 C8 C9 -1.7(2) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C11 C8 C9 C10 179.86(16) . . . . ?
C8 C9 C10 C5 1.9(3) . . . . ?
C4 C5 C10 C9 -179.83(18) . . . . ?
C6 C5 C10 C9 0.3(3) . . . . ?
C7 C8 C11 C12 2.1(2) . . . . ?
C9 C8 C11 C12 -178.86(15) . . . . ?
C7 C8 C11 C15 -177.18(14) . . . . ?
C9 C8 C11 C15 1.8(2) . . . . ?
C8 C11 C12 C13 1.4(2) . . . . ?
C15 C11 C12 C13 -179.29(14) . . . . ?
C8 C11 C12 C17 -177.71(14) . . . . ?
C15 C11 C12 C17 1.6(2) . . . . ?
C11 C12 C13 C14 -2.8(2) . . . . ?
C17 C12 C13 C14 176.35(14) . . . . ?
C11 C12 C13 C19 173.29(15) . . . . ?
C17 C12 C13 C19 -7.6(2) . . . . ?
C12 C13 C14 C7 0.6(2) . . . . ?
C19 C13 C14 C7 -175.54(15) . . . . ?
C8 C7 C14 C13 2.9(2) . . . . ?
C6 C7 C14 C13 -178.67(14) . . . . ?
C16 O2 C15 O1 -8.0(2) . . . . ?
C16 O2 C15 C11 172.35(13) . . . . ?
C12 C11 C15 O1 126.61(19) . . . . ?
C8 C11 C15 O1 -54.1(2) . . . . ?
C12 C11 C15 O2 -53.74(19) . . . . ?
C8 C11 C15 O2 125.60(15) . . . . ?
C18 O4 C17 O3 -2.8(2) . . . . ?
C18 O4 C17 C12 177.29(15) . . . . ?
C11 C12 C17 O3 126.71(18) . . . . ?
C13 C12 C17 O3 -52.4(2) . . . . ?
C11 C12 C17 O4 -53.33(19) . . . . ?
C13 C12 C17 O4 127.57(15) . . . . ?
C14 C13 C19 C21 89.09(18) . . . . ?
C12 C13 C19 C21 -86.91(19) . . . . ?
C14 C13 C19 C20 -34.5(2) . . . . ?
C12 C13 C19 C20 149.52(17) . . . . ?
C22 O6 C21 O5 -1.1(4) . . . . ?
C22 O6 C21 C19 -178.4(2) . . . . ?
C20 C19 C21 O5 26.4(3) . . . . ?
C13 C19 C21 O5 -99.4(3) . . . . ?
C20 C19 C21 O6 -156.39(17) . . . . ?
C13 C19 C21 O6 77.8(2) . . . . ?
C21 O6 C22 C23 157.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042


data_cd26205
_database_code_depnum_ccdc_archive 'CCDC 648597'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H23 O5 P'
_chemical_formula_weight         458.42

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'
P P 0.1023 0.0942 '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)/c

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                   11.330(10)
_cell_length_b                   22.000(19)
_cell_length_c                   9.420(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.108(15)
_cell_angle_gamma                90.00
_cell_volume                     2324(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3229
_cell_measurement_theta_min      4.744
_cell_measurement_theta_max      48.218

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.374
_exptl_crystal_size_min          0.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7991
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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_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            13454
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5044
_reflns_number_gt                3417
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0870P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5044
_refine_ls_number_parameters     307
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.071
_refine_ls_shift/su_mean         0.008

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
P1 P 0.64897(4) 0.86440(2) 0.84238(6) 0.04338(19) Uani 1 1 d . A .
O1 O 0.70827(12) 0.80745(6) 0.80785(16) 0.0542(4) Uani 1 1 d . . .
O2 O 0.05141(19) 0.85899(12) 0.5515(3) 0.1275(10) Uani 1 1 d . A .
O3 O 0.07134(15) 0.78633(8) 0.7132(2) 0.0853(6) Uani 1 1 d . A .
O4 O 0.1143(2) 0.91625(11) 0.8926(3) 0.1219(9) Uani 1 1 d D . .
O5 O 0.1853(2) 0.84309(13) 1.0333(3) 0.1175(9) Uani 1 1 d . . .
C1 C 0.40253(18) 0.87327(9) 0.8807(2) 0.0483(5) Uani 1 1 d . A .
C2 C 0.27862(19) 0.86253(10) 0.8305(3) 0.0509(5) Uani 1 1 d . . .
C3 C 0.24094(18) 0.84159(9) 0.6938(2) 0.0492(5) Uani 1 1 d . A .
C4 C 0.32336(18) 0.82872(9) 0.5985(2) 0.0460(5) Uani 1 1 d . . .
C5 C 0.2848(2) 0.80667(10) 0.4565(3) 0.0578(6) Uani 1 1 d . A .
H5 H 0.2039 0.8007 0.4260 0.069 Uiso 1 1 calc R . .
C6 C 0.3645(2) 0.79451(11) 0.3665(3) 0.0641(7) Uani 1 1 d . . .
H6 H 0.3383 0.7809 0.2740 0.077 Uiso 1 1 calc R A .
C7 C 0.4861(2) 0.80243(11) 0.4123(3) 0.0625(6) Uani 1 1 d . A .
H7 H 0.5404 0.7936 0.3499 0.075 Uiso 1 1 calc R . .
C8 C 0.5268(2) 0.82298(10) 0.5474(2) 0.0538(6) Uani 1 1 d . . .
H8 H 0.6083 0.8280 0.5747 0.065 Uiso 1 1 calc R A .
C9 C 0.44726(17) 0.83679(9) 0.6472(2) 0.0428(5) Uani 1 1 d . A .
C10 C 0.48564(17) 0.85918(8) 0.7918(2) 0.0422(5) Uani 1 1 d . . .
C11 C 0.4323(2) 0.90144(13) 1.0295(3) 0.0757(8) Uani 1 1 d . . .
H11A H 0.4598 0.8703 1.0976 0.114 Uiso 1 1 calc R A .
H11B H 0.3622 0.9202 1.0564 0.114 Uiso 1 1 calc R . .
H11C H 0.4935 0.9315 1.0281 0.114 Uiso 1 1 calc R . .
C12 C 0.69168(19) 0.92976(9) 0.7461(2) 0.0469(5) Uani 1 1 d . . .
C13 C 0.6136(2) 0.97563(11) 0.6942(3) 0.0633(6) Uani 1 1 d . A .
H13 H 0.5337 0.9734 0.7068 0.076 Uiso 1 1 calc R . .
C14 C 0.6549(3) 1.02506(12) 0.6231(3) 0.0778(8) Uani 1 1 d . . .
H14 H 0.6024 1.0557 0.5874 0.093 Uiso 1 1 calc R A .
C15 C 0.7727(3) 1.02865(13) 0.6057(3) 0.0812(9) Uani 1 1 d . A .
H15 H 0.7996 1.0617 0.5577 0.097 Uiso 1 1 calc R . .
C16 C 0.8509(3) 0.98411(13) 0.6583(3) 0.0795(8) Uani 1 1 d . . .
H16 H 0.9311 0.9872 0.6477 0.095 Uiso 1 1 calc R A .
C17 C 0.8109(2) 0.93486(11) 0.7266(3) 0.0639(6) Uani 1 1 d . A .
H17 H 0.8642 0.9043 0.7606 0.077 Uiso 1 1 calc R . .
C18 C 0.69626(17) 0.88172(10) 1.0297(2) 0.0464(5) Uani 1 1 d . . .
C19 C 0.7322(2) 0.93897(11) 1.0799(3) 0.0630(6) Uani 1 1 d . A .
H19 H 0.7265 0.9719 1.0172 0.076 Uiso 1 1 calc R . .
C20 C 0.7770(3) 0.94729(14) 1.2241(3) 0.0837(9) Uani 1 1 d . . .
H20 H 0.8007 0.9858 1.2575 0.100 Uiso 1 1 calc R A .
C21 C 0.7864(3) 0.89892(15) 1.3174(3) 0.0825(9) Uani 1 1 d . A .
H21 H 0.8159 0.9049 1.4136 0.099 Uiso 1 1 calc R . .
C22 C 0.7527(2) 0.84257(13) 1.2697(3) 0.0689(7) Uani 1 1 d . . .
H22 H 0.7595 0.8099 1.3332 0.083 Uiso 1 1 calc R A .
C23 C 0.70817(19) 0.83347(11) 1.1269(2) 0.0549(6) Uani 1 1 d . A .
H23 H 0.6858 0.7946 1.0952 0.066 Uiso 1 1 calc R . .
C24 C 0.1108(2) 0.83141(12) 0.6427(3) 0.0658(7) Uani 1 1 d . . .
C25 C -0.0539(3) 0.76860(19) 0.6683(5) 0.1173(16) Uani 1 1 d . . .
H25A H -0.1056 0.7976 0.7041 0.136 Uiso 1 1 calc R A .
H25B H -0.0676 0.7291 0.7060 0.136 Uiso 1 1 calc R . .
H25C H -0.0698 0.7675 0.5655 0.136 Uiso 1 1 calc R . .
C26 C 0.1868(3) 0.87514(17) 0.9242(4) 0.0924(11) Uani 1 1 d . A .
C27 C 0.0866(4) 0.8675(3) 1.1078(6) 0.085(2) Uani 0.514(8) 1 d P A 1
H27A H 0.0817 0.8441 1.1929 0.128 Uiso 0.514(8) 1 calc PR A 1
H27B H 0.0124 0.8647 1.0448 0.128 Uiso 0.514(8) 1 calc PR A 1
H27C H 0.1025 0.9092 1.1334 0.128 Uiso 0.514(8) 1 calc PR A 1
C27' C 0.0373(4) 0.9168(3) 1.0262(6) 0.113(4) Uani 0.486(8) 1 d PRD A 2
H27D H 0.0888 0.9246 1.1142 0.129 Uiso 0.486(8) 1 d PR A 2
H27E H -0.0004 0.8780 1.0317 0.129 Uiso 0.486(8) 1 d PR A 2
H27F H -0.0226 0.9479 1.0109 0.129 Uiso 0.486(8) 1 d PR 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
P1 0.0367(3) 0.0401(3) 0.0532(3) -0.0016(2) 0.0058(2) 0.0014(2)
O1 0.0470(8) 0.0443(8) 0.0722(10) -0.0046(7) 0.0114(7) 0.0068(6)
O2 0.0540(12) 0.147(2) 0.169(2) 0.0608(18) -0.0275(14) -0.0070(13)
O3 0.0547(11) 0.0784(13) 0.1274(17) -0.0025(11) 0.0285(11) -0.0197(9)
O4 0.0740(14) 0.1028(17) 0.202(3) -0.0259(17) 0.0643(16) 0.0197(13)
O5 0.1051(19) 0.151(2) 0.1107(19) -0.0111(17) 0.0635(15) 0.0021(16)
C1 0.0415(11) 0.0471(12) 0.0561(13) -0.0056(10) 0.0068(9) 0.0035(9)
C2 0.0405(11) 0.0473(12) 0.0664(14) -0.0003(10) 0.0128(10) 0.0036(9)
C3 0.0385(11) 0.0411(12) 0.0675(15) 0.0062(10) 0.0055(10) 0.0000(9)
C4 0.0462(12) 0.0373(11) 0.0530(13) 0.0049(9) 0.0016(9) -0.0026(9)
C5 0.0548(14) 0.0536(14) 0.0614(15) 0.0003(11) -0.0049(11) -0.0088(11)
C6 0.0769(18) 0.0602(15) 0.0526(14) -0.0087(11) 0.0002(13) -0.0106(13)
C7 0.0723(17) 0.0618(15) 0.0552(14) -0.0088(11) 0.0155(12) -0.0025(12)
C8 0.0472(12) 0.0559(14) 0.0594(14) -0.0089(11) 0.0111(10) -0.0030(10)
C9 0.0394(11) 0.0377(11) 0.0517(12) 0.0017(9) 0.0075(9) -0.0010(8)
C10 0.0388(10) 0.0373(11) 0.0507(12) -0.0014(9) 0.0069(9) 0.0023(8)
C11 0.0511(14) 0.101(2) 0.0758(18) -0.0358(15) 0.0137(12) 0.0082(14)
C12 0.0520(12) 0.0424(12) 0.0455(11) -0.0030(9) 0.0034(9) -0.0035(9)
C13 0.0645(15) 0.0552(14) 0.0672(15) 0.0053(12) -0.0015(12) -0.0009(12)
C14 0.097(2) 0.0537(16) 0.0780(18) 0.0138(13) -0.0045(16) 0.0021(15)
C15 0.113(3) 0.0600(17) 0.0714(18) 0.0083(14) 0.0177(17) -0.0213(17)
C16 0.0789(19) 0.0721(19) 0.092(2) 0.0011(16) 0.0287(16) -0.0200(15)
C17 0.0595(15) 0.0565(15) 0.0781(17) 0.0051(12) 0.0185(12) -0.0040(12)
C18 0.0373(11) 0.0487(12) 0.0526(12) 0.0027(10) 0.0040(9) 0.0001(9)
C19 0.0769(17) 0.0521(14) 0.0582(14) 0.0005(11) 0.0038(12) -0.0097(12)
C20 0.106(2) 0.078(2) 0.0645(17) -0.0145(15) 0.0036(16) -0.0241(17)
C21 0.095(2) 0.098(2) 0.0501(15) 0.0019(15) -0.0037(14) -0.0044(17)
C22 0.0705(17) 0.0777(19) 0.0581(16) 0.0149(13) 0.0080(13) 0.0109(14)
C23 0.0468(12) 0.0546(14) 0.0636(15) 0.0054(11) 0.0082(10) 0.0048(10)
C24 0.0428(13) 0.0673(17) 0.0870(19) -0.0018(14) 0.0081(13) -0.0028(12)
C25 0.065(2) 0.102(3) 0.151(5) -0.040(3) 0.041(2) -0.053(2)
C26 0.0536(17) 0.107(3) 0.125(3) -0.055(2) 0.0419(18) -0.0218(17)
C27 0.077(4) 0.110(5) 0.075(4) 0.002(3) 0.036(3) 0.004(3)
C27' 0.071(4) 0.159(8) 0.117(6) -0.018(6) 0.043(4) 0.041(4)

_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
P1 O1 1.4793(17) . ?
P1 C12 1.802(2) . ?
P1 C18 1.811(3) . ?
P1 C10 1.848(3) . ?
O2 C24 1.182(3) . ?
O3 C24 1.307(3) . ?
O3 C25 1.474(4) . ?
O4 C26 1.230(4) . ?
O4 C27' 1.630(5) . ?
O5 C26 1.248(5) . ?
O5 C27 1.501(5) . ?
C1 C10 1.381(3) . ?
C1 C2 1.436(3) . ?
C1 C11 1.526(3) . ?
C2 C3 1.378(3) . ?
C2 C26 1.482(4) . ?
C3 C4 1.412(3) . ?
C3 C24 1.501(3) . ?
C4 C9 1.425(3) . ?
C4 C5 1.432(3) . ?
C5 C6 1.350(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.424(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.456(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.385(3) . ?
C12 C17 1.393(3) . ?
C13 C14 1.392(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.386(3) . ?
C18 C23 1.396(3) . ?
C19 C20 1.394(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.355(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C27 H27D 1.2586 . ?
C27 H27E 1.1568 . ?
C27' H27D 0.9600 . ?
C27' H27E 0.9600 . ?
C27' H27F 0.9600 . ?

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
O1 P1 C12 113.73(11) . . ?
O1 P1 C18 108.14(9) . . ?
C12 P1 C18 105.00(11) . . ?
O1 P1 C10 111.11(9) . . ?
C12 P1 C10 104.48(10) . . ?
C18 P1 C10 114.34(10) . . ?
C24 O3 C25 116.1(3) . . ?
C26 O4 C27' 103.4(4) . . ?
C26 O5 C27 106.3(4) . . ?
C10 C1 C2 118.8(2) . . ?
C10 C1 C11 124.54(19) . . ?
C2 C1 C11 116.63(19) . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 C26 117.9(2) . . ?
C1 C2 C26 120.6(2) . . ?
C2 C3 C4 121.03(19) . . ?
C2 C3 C24 120.7(2) . . ?
C4 C3 C24 118.3(2) . . ?
C3 C4 C9 118.71(19) . . ?
C3 C4 C5 121.3(2) . . ?
C9 C4 C5 120.0(2) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 121.2(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 121.5(2) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C4 116.59(19) . . ?
C8 C9 C10 123.81(18) . . ?
C4 C9 C10 119.59(18) . . ?
C1 C10 C9 120.27(18) . . ?
C1 C10 P1 125.00(16) . . ?
C9 C10 P1 114.72(14) . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 118.6(2) . . ?
C13 C12 P1 123.73(19) . . ?
C17 C12 P1 117.69(17) . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 121.1(2) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C19 C18 C23 118.1(2) . . ?
C19 C18 P1 123.76(17) . . ?
C23 C18 P1 117.86(18) . . ?
C18 C19 C20 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.1(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 121.1(2) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
O2 C24 O3 123.9(3) . . ?
O2 C24 C3 126.1(3) . . ?
O3 C24 C3 110.0(2) . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 O5 121.9(3) . . ?
O4 C26 C2 119.6(4) . . ?
O5 C26 C2 118.5(3) . . ?
O5 C27 H27A 109.5 . . ?
O5 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O5 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O5 C27 H27D 111.6 . . ?
H27A C27 H27D 119.8 . . ?
H27B C27 H27D 96.0 . . ?
H27C C27 H27D 14.2 . . ?
O5 C27 H27E 114.0 . . ?
H27A C27 H27E 118.7 . . ?
H27B C27 H27E 15.2 . . ?
H27C C27 H27E 94.5 . . ?
H27D C27 H27E 80.8 . . ?
O4 C27' H27D 110.0 . . ?
O4 C27' H27E 108.9 . . ?
H27D C27' H27E 109.5 . . ?
O4 C27' H27F 109.5 . . ?
H27D C27' H27F 109.5 . . ?
H27E C27' H27F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -3.4(3) . . . . ?
C11 C1 C2 C3 175.0(2) . . . . ?
C10 C1 C2 C26 178.0(3) . . . . ?
C11 C1 C2 C26 -3.5(3) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C26 C2 C3 C4 179.9(2) . . . . ?
C1 C2 C3 C24 -179.2(2) . . . . ?
C26 C2 C3 C24 -0.6(4) . . . . ?
C2 C3 C4 C9 1.1(3) . . . . ?
C24 C3 C4 C9 -178.45(19) . . . . ?
C2 C3 C4 C5 179.7(2) . . . . ?
C24 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -180.0(2) . . . . ?
C9 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C4 -0.6(3) . . . . ?
C7 C8 C9 C10 -179.6(2) . . . . ?
C3 C4 C9 C8 179.74(19) . . . . ?
C5 C4 C9 C8 1.1(3) . . . . ?
C3 C4 C9 C10 -1.3(3) . . . . ?
C5 C4 C9 C10 -179.94(18) . . . . ?
C2 C1 C10 C9 3.1(3) . . . . ?
C11 C1 C10 C9 -175.2(2) . . . . ?
C2 C1 C10 P1 -175.20(15) . . . . ?
C11 C1 C10 P1 6.5(3) . . . . ?
C8 C9 C10 C1 178.0(2) . . . . ?
C4 C9 C10 C1 -0.8(3) . . . . ?
C8 C9 C10 P1 -3.5(3) . . . . ?
C4 C9 C10 P1 177.64(14) . . . . ?
O1 P1 C10 C1 129.56(18) . . . . ?
C12 P1 C10 C1 -107.40(19) . . . . ?
C18 P1 C10 C1 6.8(2) . . . . ?
O1 P1 C10 C9 -48.84(17) . . . . ?
C12 P1 C10 C9 74.20(17) . . . . ?
C18 P1 C10 C9 -171.58(14) . . . . ?
O1 P1 C12 C13 142.41(18) . . . . ?
C18 P1 C12 C13 -99.6(2) . . . . ?
C10 P1 C12 C13 21.1(2) . . . . ?
O1 P1 C12 C17 -39.4(2) . . . . ?
C18 P1 C12 C17 78.66(19) . . . . ?
C10 P1 C12 C17 -160.68(18) . . . . ?
C17 C12 C13 C14 0.7(3) . . . . ?
P1 C12 C13 C14 178.87(19) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 C17 1.2(4) . . . . ?
C15 C16 C17 C12 -1.2(4) . . . . ?
C13 C12 C17 C16 0.3(4) . . . . ?
P1 C12 C17 C16 -178.1(2) . . . . ?
O1 P1 C18 C19 134.2(2) . . . . ?
C12 P1 C18 C19 12.4(2) . . . . ?
C10 P1 C18 C19 -101.5(2) . . . . ?
O1 P1 C18 C23 -39.32(19) . . . . ?
C12 P1 C18 C23 -161.08(17) . . . . ?
C10 P1 C18 C23 85.01(18) . . . . ?
C23 C18 C19 C20 -1.0(4) . . . . ?
P1 C18 C19 C20 -174.5(2) . . . . ?
C18 C19 C20 C21 0.3(4) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C21 C22 C23 C18 -0.4(4) . . . . ?
C19 C18 C23 C22 1.1(3) . . . . ?
P1 C18 C23 C22 174.93(18) . . . . ?
C25 O3 C24 O2 2.8(4) . . . . ?
C25 O3 C24 C3 -176.4(2) . . . . ?
C2 C3 C24 O2 113.5(3) . . . . ?
C4 C3 C24 O2 -67.0(4) . . . . ?
C2 C3 C24 O3 -67.3(3) . . . . ?
C4 C3 C24 O3 112.2(2) . . . . ?
C27' O4 C26 O5 3.6(4) . . . . ?
C27' O4 C26 C2 -176.8(3) . . . . ?
C27 O5 C26 O4 -2.1(5) . . . . ?
C27 O5 C26 C2 178.3(3) . . . . ?
C3 C2 C26 O4 -65.3(3) . . . . ?
C1 C2 C26 O4 113.3(3) . . . . ?
C3 C2 C26 O5 114.3(3) . . . . ?
C1 C2 C26 O5 -67.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.044