# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Shu-Jiang Tu'
_publ_contact_author_email       LAOTU@XZNU.EDU.CN

_publ_section_title              
;
A new domino autocatalytic reaction leading to
polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes
;
loop_
_publ_author_name
'Shu Tu'
'Wen-Juan Hao'
'Bo Jiang'
'Feng Shi'
'Jin-Peng Zhang'

# Attachment '3g.cif'

data_041208c
_database_code_depnum_ccdc_archive 'CCDC 658845'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 F2 O6'
_chemical_formula_weight         458.44

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'
F F 0.0171 0.0103 '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                   8.146(4)
_cell_length_b                   10.714(5)
_cell_length_c                   13.580(7)
_cell_angle_alpha                69.230(7)
_cell_angle_beta                 85.432(7)
_cell_angle_gamma                89.137(7)
_cell_volume                     1104.6(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2045
_cell_measurement_theta_min      2.861
_cell_measurement_theta_max      27.188

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9507
_exptl_absorpt_correction_T_max  0.9692
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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            5811
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3845
_reflns_number_gt                2566
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.0636P)^2^+0.7548P] 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         3845
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1562
_refine_ls_wR_factor_gt          0.1330
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
F1 F 0.2225(2) -0.55832(16) 0.80880(16) 0.0705(5) Uani 1 1 d . . .
F2 F -0.4492(2) 0.3844(2) 0.92709(16) 0.0810(6) Uani 1 1 d . . .
O1 O -0.2377(3) -0.0938(3) 0.77052(17) 0.0824(8) Uani 1 1 d . . .
O2 O -0.0465(3) -0.1034(3) 0.89750(16) 0.0759(7) Uani 1 1 d . . .
O3 O -0.1986(3) 0.0275(2) 0.60643(16) 0.0599(6) Uani 1 1 d . . .
O4 O 0.1784(2) 0.0146(2) 0.85765(16) 0.0571(5) Uani 1 1 d . . .
O5 O 0.2207(2) 0.2679(2) 0.47709(16) 0.0577(6) Uani 1 1 d . . .
O6 O 0.4326(3) 0.2993(2) 0.56250(16) 0.0595(6) Uani 1 1 d . . .
C1 C 0.0155(3) 0.0433(3) 0.7132(2) 0.0400(6) Uani 1 1 d . . .
C2 C -0.1477(3) -0.0066(3) 0.6921(2) 0.0449(7) Uani 1 1 d . . .
C3 C 0.0551(3) -0.0133(3) 0.8275(2) 0.0441(6) Uani 1 1 d . . .
C4 C -0.2064(4) -0.1416(3) 0.8792(2) 0.0567(8) Uani 1 1 d . . .
C5 C -0.2065(5) -0.2904(4) 0.9131(3) 0.0810(11) Uani 1 1 d . . .
H5A H -0.1857 -0.3283 0.9863 0.121 Uiso 1 1 calc R . .
H5B H -0.1221 -0.3171 0.8714 0.121 Uiso 1 1 calc R . .
H5C H -0.3118 -0.3213 0.9032 0.121 Uiso 1 1 calc R . .
C6 C -0.3320(4) -0.0855(4) 0.9370(3) 0.0793(11) Uani 1 1 d . . .
H6A H -0.3126 -0.1166 1.0105 0.119 Uiso 1 1 calc R . .
H6B H -0.4399 -0.1138 0.9291 0.119 Uiso 1 1 calc R . .
H6C H -0.3247 0.0103 0.9085 0.119 Uiso 1 1 calc R . .
C7 C 0.1539(3) -0.0009(3) 0.6429(2) 0.0457(7) Uani 1 1 d . . .
H7 H 0.1109 0.0187 0.5736 0.055 Uiso 1 1 calc R . .
C8 C 0.3125(3) 0.0785(3) 0.6233(2) 0.0524(7) Uani 1 1 d . . .
H8A H 0.3873 0.0534 0.5744 0.063 Uiso 1 1 calc R . .
H8B H 0.3639 0.0568 0.6892 0.063 Uiso 1 1 calc R . .
C9 C 0.2843(4) 0.2287(3) 0.5779(2) 0.0487(7) Uani 1 1 d . . .
C10 C 0.1673(4) 0.2697(3) 0.6525(2) 0.0535(7) Uani 1 1 d . . .
H10A H 0.1508 0.3653 0.6228 0.064 Uiso 1 1 calc R . .
H10B H 0.2165 0.2505 0.7190 0.064 Uiso 1 1 calc R . .
C11 C 0.0019(3) 0.1989(3) 0.6735(2) 0.0463(7) Uani 1 1 d . . .
H11 H -0.0457 0.2253 0.6052 0.056 Uiso 1 1 calc R . .
C12 C 0.1776(3) -0.1506(3) 0.6875(2) 0.0433(6) Uani 1 1 d . . .
C13 C 0.0832(3) -0.2327(3) 0.6541(2) 0.0482(7) Uani 1 1 d . . .
H13 H 0.0095 -0.1943 0.6031 0.058 Uiso 1 1 calc R . .
C14 C 0.0961(4) -0.3695(3) 0.6948(2) 0.0530(7) Uani 1 1 d . . .
H14 H 0.0316 -0.4238 0.6726 0.064 Uiso 1 1 calc R . .
C15 C 0.2065(4) -0.4233(3) 0.7689(2) 0.0490(7) Uani 1 1 d . . .
C16 C 0.3028(4) -0.3477(3) 0.8040(2) 0.0540(7) Uani 1 1 d . . .
H16 H 0.3766 -0.3873 0.8545 0.065 Uiso 1 1 calc R . .
C17 C 0.2880(4) -0.2110(3) 0.7627(2) 0.0519(7) Uani 1 1 d . . .
H17 H 0.3534 -0.1579 0.7857 0.062 Uiso 1 1 calc R . .
C18 C -0.1181(3) 0.2459(3) 0.7451(2) 0.0438(6) Uani 1 1 d . . .
C19 C -0.0775(3) 0.2540(3) 0.8398(2) 0.0513(7) Uani 1 1 d . . .
H19 H 0.0268 0.2284 0.8622 0.062 Uiso 1 1 calc R . .
C20 C -0.1884(4) 0.2993(3) 0.9021(2) 0.0565(8) Uani 1 1 d . . .
H20 H -0.1598 0.3040 0.9656 0.068 Uiso 1 1 calc R . .
C21 C -0.3405(4) 0.3367(3) 0.8676(3) 0.0562(8) Uani 1 1 d . . .
C22 C -0.3872(4) 0.3290(3) 0.7759(3) 0.0638(9) Uani 1 1 d . . .
H22 H -0.4922 0.3540 0.7546 0.077 Uiso 1 1 calc R . .
C23 C -0.2745(4) 0.2828(3) 0.7149(2) 0.0561(8) Uani 1 1 d . . .
H23 H -0.3053 0.2768 0.6522 0.067 Uiso 1 1 calc R . .
C24 C 0.3604(5) 0.2958(4) 0.4018(3) 0.0773(11) Uani 1 1 d . . .
H24A H 0.3406 0.3718 0.3390 0.093 Uiso 1 1 calc R . .
H24B H 0.3867 0.2192 0.3814 0.093 Uiso 1 1 calc R . .
C25 C 0.4959(5) 0.3257(4) 0.4579(3) 0.0809(11) Uani 1 1 d . . .
H25A H 0.5899 0.2698 0.4559 0.097 Uiso 1 1 calc R . .
H25B H 0.5307 0.4185 0.4250 0.097 Uiso 1 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
F1 0.0761(13) 0.0424(10) 0.0900(14) -0.0193(9) -0.0097(10) 0.0052(9)
F2 0.0676(12) 0.0951(15) 0.0837(14) -0.0406(12) 0.0124(10) 0.0235(11)
O1 0.0664(15) 0.116(2) 0.0471(13) -0.0047(13) -0.0079(11) -0.0462(14)
O2 0.0620(14) 0.1014(19) 0.0436(12) 0.0026(12) -0.0113(10) -0.0321(13)
O3 0.0588(13) 0.0732(15) 0.0470(12) -0.0188(11) -0.0133(10) 0.0037(11)
O4 0.0473(12) 0.0660(14) 0.0633(13) -0.0274(11) -0.0136(10) -0.0032(10)
O5 0.0464(12) 0.0682(14) 0.0631(13) -0.0292(11) -0.0012(10) -0.0077(10)
O6 0.0575(13) 0.0660(14) 0.0548(12) -0.0224(10) 0.0040(10) -0.0130(10)
C1 0.0376(14) 0.0411(15) 0.0392(14) -0.0126(12) 0.0017(11) 0.0000(11)
C2 0.0426(16) 0.0482(16) 0.0451(16) -0.0184(13) -0.0019(13) 0.0038(12)
C3 0.0380(15) 0.0450(16) 0.0505(16) -0.0188(13) -0.0024(13) 0.0005(12)
C4 0.0503(18) 0.072(2) 0.0416(16) -0.0125(15) 0.0016(13) -0.0203(15)
C5 0.090(3) 0.079(3) 0.071(2) -0.025(2) 0.010(2) -0.015(2)
C6 0.069(2) 0.094(3) 0.084(3) -0.043(2) -0.001(2) -0.008(2)
C7 0.0451(16) 0.0461(16) 0.0433(15) -0.0136(13) 0.0012(12) 0.0031(12)
C8 0.0459(17) 0.0572(18) 0.0529(17) -0.0199(14) 0.0054(13) -0.0010(13)
C9 0.0519(17) 0.0516(17) 0.0429(16) -0.0187(13) 0.0053(13) -0.0032(13)
C10 0.0549(18) 0.0491(17) 0.0585(18) -0.0232(14) 0.0043(14) -0.0044(14)
C11 0.0463(16) 0.0434(16) 0.0463(16) -0.0138(13) 0.0032(12) 0.0028(12)
C12 0.0406(15) 0.0453(16) 0.0416(15) -0.0143(12) 0.0049(12) 0.0035(12)
C13 0.0474(16) 0.0537(18) 0.0460(16) -0.0209(14) -0.0044(13) 0.0053(13)
C14 0.0493(17) 0.0541(19) 0.0623(19) -0.0294(15) -0.0009(15) -0.0013(14)
C15 0.0512(17) 0.0386(16) 0.0551(17) -0.0156(13) 0.0022(14) 0.0060(13)
C16 0.0545(18) 0.0504(18) 0.0582(18) -0.0191(15) -0.0127(14) 0.0114(14)
C17 0.0504(17) 0.0494(18) 0.0613(19) -0.0253(15) -0.0091(14) 0.0015(14)
C18 0.0418(15) 0.0390(15) 0.0469(16) -0.0117(12) 0.0018(12) 0.0016(12)
C19 0.0371(15) 0.0524(18) 0.066(2) -0.0227(15) -0.0036(14) 0.0046(13)
C20 0.0568(19) 0.061(2) 0.0551(18) -0.0262(15) -0.0016(15) 0.0064(15)
C21 0.0478(18) 0.0577(19) 0.062(2) -0.0233(16) 0.0111(15) 0.0093(14)
C22 0.0449(18) 0.075(2) 0.073(2) -0.0277(18) -0.0081(16) 0.0181(15)
C23 0.0527(18) 0.064(2) 0.0518(18) -0.0209(15) -0.0075(14) 0.0130(15)
C24 0.076(2) 0.099(3) 0.051(2) -0.0219(19) 0.0095(18) -0.021(2)
C25 0.068(2) 0.107(3) 0.065(2) -0.031(2) 0.0183(18) -0.029(2)

_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
F1 C15 1.361(3) . ?
F2 C21 1.365(3) . ?
O1 C2 1.317(3) . ?
O1 C4 1.424(3) . ?
O2 C3 1.330(3) . ?
O2 C4 1.437(4) . ?
O3 C2 1.195(3) . ?
O4 C3 1.195(3) . ?
O5 C9 1.421(3) . ?
O5 C24 1.428(4) . ?
O6 C9 1.397(3) . ?
O6 C25 1.402(4) . ?
C1 C3 1.512(4) . ?
C1 C2 1.526(4) . ?
C1 C11 1.565(4) . ?
C1 C7 1.594(4) . ?
C4 C6 1.487(5) . ?
C4 C5 1.494(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.511(4) . ?
C7 C12 1.516(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.526(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.510(4) . ?
C10 C11 1.513(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C18 1.527(4) . ?
C11 H11 0.9800 . ?
C12 C13 1.388(4) . ?
C12 C17 1.390(4) . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.360(4) . ?
C16 C17 1.378(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.379(4) . ?
C18 C19 1.385(4) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.364(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.360(4) . ?
C22 C23 1.389(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.490(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?

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
C2 O1 C4 126.6(2) . . ?
C3 O2 C4 126.1(2) . . ?
C9 O5 C24 106.1(2) . . ?
C9 O6 C25 107.8(2) . . ?
C3 C1 C2 114.2(2) . . ?
C3 C1 C11 111.5(2) . . ?
C2 C1 C11 105.3(2) . . ?
C3 C1 C7 109.0(2) . . ?
C2 C1 C7 105.9(2) . . ?
C11 C1 C7 110.8(2) . . ?
O3 C2 O1 117.2(3) . . ?
O3 C2 C1 123.3(3) . . ?
O1 C2 C1 119.5(2) . . ?
O4 C3 O2 117.7(3) . . ?
O4 C3 C1 122.9(3) . . ?
O2 C3 C1 119.3(2) . . ?
O1 C4 O2 113.3(2) . . ?
O1 C4 C6 108.4(3) . . ?
O2 C4 C6 108.0(3) . . ?
O1 C4 C5 105.8(3) . . ?
O2 C4 C5 106.1(3) . . ?
C6 C4 C5 115.5(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 113.5(2) . . ?
C8 C7 C1 113.1(2) . . ?
C12 C7 C1 110.7(2) . . ?
C8 C7 H7 106.3 . . ?
C12 C7 H7 106.3 . . ?
C1 C7 H7 106.3 . . ?
C7 C8 C9 112.1(2) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O6 C9 O5 105.9(2) . . ?
O6 C9 C10 108.8(2) . . ?
O5 C9 C10 109.6(2) . . ?
O6 C9 C8 110.8(2) . . ?
O5 C9 C8 111.7(2) . . ?
C10 C9 C8 110.0(2) . . ?
C9 C10 C11 112.8(2) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C18 112.3(2) . . ?
C10 C11 C1 113.2(2) . . ?
C18 C11 C1 112.4(2) . . ?
C10 C11 H11 106.1 . . ?
C18 C11 H11 106.1 . . ?
C1 C11 H11 106.1 . . ?
C13 C12 C17 117.8(3) . . ?
C13 C12 C7 119.2(2) . . ?
C17 C12 C7 123.0(3) . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 118.1(3) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C16 C15 F1 118.3(3) . . ?
C16 C15 C14 122.9(3) . . ?
F1 C15 C14 118.8(3) . . ?
C15 C16 C17 118.3(3) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C16 C17 C12 121.4(3) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
C23 C18 C19 117.6(3) . . ?
C23 C18 C11 119.2(3) . . ?
C19 C18 C11 123.2(2) . . ?
C18 C19 C20 121.8(3) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C21 C20 C19 118.2(3) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
C22 C21 C20 122.4(3) . . ?
C22 C21 F2 118.9(3) . . ?
C20 C21 F2 118.6(3) . . ?
C21 C22 C23 118.5(3) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C18 C23 C22 121.5(3) . . ?
C18 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
O5 C24 C25 104.3(3) . . ?
O5 C24 H24A 110.9 . . ?
C25 C24 H24A 110.9 . . ?
O5 C24 H24B 110.9 . . ?
C25 C24 H24B 110.9 . . ?
H24A C24 H24B 108.9 . . ?
O6 C25 C24 106.5(3) . . ?
O6 C25 H25A 110.4 . . ?
C24 C25 H25A 110.4 . . ?
O6 C25 H25B 110.4 . . ?
C24 C25 H25B 110.4 . . ?
H25A C25 H25B 108.6 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043

# Attachment 'revised_3e1.cif'

data_041203c
_database_code_depnum_ccdc_archive 'CCDC 658846'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H30 O8'
_chemical_formula_weight         482.51

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   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                   9.977(5)
_cell_length_b                   20.162(9)
_cell_length_c                   12.508(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.934(8)
_cell_angle_gamma                90.00
_cell_volume                     2507(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1366
_cell_measurement_theta_min      2.285
_cell_measurement_theta_max      19.535

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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            11754
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_av_sigmaI/netI    0.1633
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4126
_reflns_number_gt                1349
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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          
;
Atom O5 is restrained with effective standard deviation 0.01 so that their
Uij components approximate to isotropic behavior.
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^)+(0.0550P)^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         4126
_refine_ls_number_parameters     316
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.2361
_refine_ls_R_factor_gt           0.0747
_refine_ls_wR_factor_ref         0.1874
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.012
_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 -0.0782(3) 0.1365(2) 0.3511(3) 0.0761(13) Uani 1 1 d . . .
O2 O 0.0250(4) 0.1844(2) 0.2024(3) 0.0751(12) Uani 1 1 d . . .
O3 O 0.0355(4) 0.10348(19) 0.4940(3) 0.0686(12) Uani 1 1 d . . .
O4 O 0.2363(4) 0.19884(18) 0.2038(3) 0.0649(11) Uani 1 1 d . . .
O5 O 0.4608(4) 0.1128(2) 0.5381(4) 0.1049(16) Uani 1 1 d U . .
O6 O 0.5876(5) 0.1554(2) 0.4129(4) 0.1001(16) Uani 1 1 d . . .
O7 O -0.0022(5) -0.1063(2) 0.0771(3) 0.0887(14) Uani 1 1 d . . .
O8 O -0.1002(4) 0.4239(2) 0.4598(4) 0.0898(14) Uani 1 1 d . . .
C1 C 0.1680(5) 0.1482(2) 0.3627(4) 0.0466(14) Uani 1 1 d . . .
C2 C 0.2380(5) 0.1994(3) 0.4430(5) 0.0615(16) Uani 1 1 d . . .
H2 H 0.2350 0.1788 0.5137 0.074 Uiso 1 1 calc R . .
C3 C 0.3789(6) 0.2090(3) 0.4312(5) 0.082(2) Uani 1 1 d . . .
H3A H 0.4153 0.2374 0.4892 0.099 Uiso 1 1 calc R . .
H3B H 0.3872 0.2327 0.3646 0.099 Uiso 1 1 calc R . .
C4 C 0.4711(8) 0.1438(3) 0.4308(5) 0.0680(18) Uani 1 1 d . . .
C5 C 0.3969(6) 0.0959(3) 0.3462(6) 0.084(2) Uani 1 1 d . . .
H5A H 0.4050 0.1141 0.2753 0.101 Uiso 1 1 calc R . .
H5B H 0.4438 0.0537 0.3498 0.101 Uiso 1 1 calc R . .
C6 C 0.2578(5) 0.0834(3) 0.3569(5) 0.0588(16) Uani 1 1 d . . .
H6 H 0.2569 0.0637 0.4284 0.071 Uiso 1 1 calc R . .
C7 C 0.0383(5) 0.1274(3) 0.4064(5) 0.0528(15) Uani 1 1 d . . .
C8 C 0.1480(6) 0.1791(2) 0.2534(5) 0.0475(14) Uani 1 1 d . . .
C9 C -0.0965(5) 0.1675(3) 0.2462(4) 0.0507(14) Uani 1 1 d . . .
C10 C -0.1679(6) 0.1184(3) 0.1731(5) 0.091(2) Uani 1 1 d . . .
H10A H -0.2520 0.1068 0.2002 0.137 Uiso 1 1 calc R . .
H10B H -0.1134 0.0794 0.1692 0.137 Uiso 1 1 calc R . .
H10C H -0.1845 0.1374 0.1029 0.137 Uiso 1 1 calc R . .
C11 C -0.1733(6) 0.2284(3) 0.2604(5) 0.090(2) Uani 1 1 d . . .
H11A H -0.2563 0.2176 0.2898 0.135 Uiso 1 1 calc R . .
H11B H -0.1922 0.2498 0.1922 0.135 Uiso 1 1 calc R . .
H11C H -0.1217 0.2577 0.3084 0.135 Uiso 1 1 calc R . .
C12 C 0.1543(5) 0.2613(3) 0.4480(5) 0.0537(15) Uani 1 1 d . . .
C13 C 0.1714(5) 0.3153(3) 0.3840(5) 0.0556(15) Uani 1 1 d . . .
H13 H 0.2404 0.3148 0.3385 0.067 Uiso 1 1 calc R . .
C14 C 0.0903(6) 0.3702(3) 0.3850(5) 0.0606(16) Uani 1 1 d . . .
H14 H 0.1028 0.4054 0.3389 0.073 Uiso 1 1 calc R . .
C15 C -0.0101(6) 0.3731(3) 0.4544(5) 0.0615(16) Uani 1 1 d . . .
C16 C -0.0247(6) 0.3210(3) 0.5229(5) 0.0660(17) Uani 1 1 d . . .
H16 H -0.0905 0.3227 0.5712 0.079 Uiso 1 1 calc R . .
C17 C 0.0572(5) 0.2659(3) 0.5209(4) 0.0560(15) Uani 1 1 d . . .
H17 H 0.0472 0.2314 0.5689 0.067 Uiso 1 1 calc R . .
C18 C -0.1000(8) 0.4737(4) 0.3811(7) 0.134(3) Uani 1 1 d . . .
H18A H -0.1667 0.5064 0.3936 0.201 Uiso 1 1 calc R . .
H18B H -0.1202 0.4544 0.3114 0.201 Uiso 1 1 calc R . .
H18C H -0.0129 0.4942 0.3844 0.201 Uiso 1 1 calc R . .
C19 C 0.1895(5) 0.0320(3) 0.2828(5) 0.0516(15) Uani 1 1 d . . .
C20 C 0.2011(5) 0.0315(3) 0.1736(5) 0.0571(15) Uani 1 1 d . . .
H20 H 0.2529 0.0640 0.1441 0.069 Uiso 1 1 calc R . .
C21 C 0.1380(6) -0.0158(3) 0.1067(5) 0.0685(17) Uani 1 1 d . . .
H21 H 0.1504 -0.0159 0.0339 0.082 Uiso 1 1 calc R . .
C22 C 0.0572(6) -0.0626(3) 0.1485(6) 0.0643(17) Uani 1 1 d . . .
C23 C 0.0439(5) -0.0631(3) 0.2572(6) 0.0610(16) Uani 1 1 d . . .
H23 H -0.0086 -0.0955 0.2861 0.073 Uiso 1 1 calc R . .
C24 C 0.1071(5) -0.0163(3) 0.3232(5) 0.0595(15) Uani 1 1 d . . .
H24 H 0.0949 -0.0167 0.3960 0.071 Uiso 1 1 calc R . .
C25 C -0.0945(7) -0.1527(3) 0.1126(6) 0.108(3) Uani 1 1 d . . .
H25A H -0.1280 -0.1801 0.0535 0.162 Uiso 1 1 calc R . .
H25B H -0.1680 -0.1296 0.1405 0.162 Uiso 1 1 calc R . .
H25C H -0.0502 -0.1799 0.1678 0.162 Uiso 1 1 calc R . .
C26 C 0.6675(6) 0.1443(4) 0.5066(6) 0.102(3) Uani 1 1 d . . .
H26A H 0.7119 0.1854 0.5290 0.123 Uiso 1 1 calc R . .
H26B H 0.7367 0.1124 0.4926 0.123 Uiso 1 1 calc R . .
C27 C 0.5964(7) 0.1206(4) 0.5904(6) 0.115(3) Uani 1 1 d . . .
H27A H 0.5981 0.1523 0.6489 0.138 Uiso 1 1 calc R . .
H27B H 0.6324 0.0786 0.6176 0.138 Uiso 1 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 0.037(2) 0.115(4) 0.076(3) 0.022(3) 0.002(2) -0.008(2)
O2 0.049(2) 0.113(4) 0.062(3) 0.026(2) -0.003(2) -0.004(2)
O3 0.076(3) 0.070(3) 0.059(3) 0.015(2) 0.000(2) -0.008(2)
O4 0.065(2) 0.064(3) 0.069(3) 0.009(2) 0.023(2) 0.004(2)
O5 0.074(3) 0.096(4) 0.152(4) -0.033(3) 0.050(3) -0.018(3)
O6 0.082(3) 0.115(4) 0.101(4) -0.004(3) -0.004(3) 0.007(3)
O7 0.100(3) 0.075(3) 0.088(3) -0.022(3) -0.005(3) -0.023(3)
O8 0.082(3) 0.064(3) 0.127(4) -0.002(3) 0.030(3) 0.031(3)
C1 0.043(3) 0.043(3) 0.054(4) 0.001(3) 0.001(3) 0.007(3)
C2 0.064(4) 0.044(4) 0.073(4) -0.017(3) -0.014(3) 0.002(3)
C3 0.067(4) 0.091(5) 0.089(5) -0.004(4) 0.010(4) 0.005(4)
C4 0.080(5) 0.072(5) 0.054(4) 0.009(4) 0.016(4) 0.006(4)
C5 0.068(4) 0.082(5) 0.106(6) 0.004(4) 0.024(4) 0.008(4)
C6 0.058(4) 0.038(4) 0.078(4) -0.012(3) -0.008(3) 0.012(3)
C7 0.048(4) 0.041(4) 0.070(4) -0.006(3) 0.009(3) 0.009(3)
C8 0.048(3) 0.040(3) 0.057(4) -0.010(3) 0.013(3) 0.003(3)
C9 0.047(3) 0.056(4) 0.047(4) 0.006(3) -0.008(3) 0.002(3)
C10 0.069(4) 0.089(5) 0.113(6) -0.024(4) -0.012(4) -0.012(4)
C11 0.085(5) 0.078(5) 0.105(6) -0.008(4) 0.000(4) 0.006(4)
C12 0.049(3) 0.042(4) 0.068(4) -0.012(3) -0.004(3) 0.004(3)
C13 0.051(3) 0.046(4) 0.069(4) -0.008(3) -0.004(3) -0.006(3)
C14 0.068(4) 0.041(4) 0.074(4) -0.008(3) 0.015(3) -0.004(3)
C15 0.056(4) 0.048(4) 0.078(5) -0.018(4) -0.002(3) 0.008(3)
C16 0.065(4) 0.062(5) 0.072(5) -0.021(4) 0.010(3) 0.006(4)
C17 0.049(3) 0.057(4) 0.063(4) -0.002(3) 0.006(3) 0.004(3)
C18 0.145(7) 0.078(6) 0.182(9) 0.026(6) 0.032(6) 0.055(6)
C19 0.049(3) 0.033(4) 0.073(5) -0.003(3) 0.004(3) 0.002(3)
C20 0.060(4) 0.047(4) 0.066(4) -0.001(3) 0.012(3) 0.003(3)
C21 0.078(4) 0.058(4) 0.069(4) -0.016(4) 0.003(4) 0.005(4)
C22 0.068(4) 0.055(5) 0.068(5) -0.020(4) -0.002(4) -0.001(4)
C23 0.058(4) 0.043(4) 0.081(5) 0.012(3) 0.002(4) -0.003(3)
C24 0.071(4) 0.042(4) 0.064(4) -0.002(3) -0.004(3) 0.001(3)
C25 0.106(6) 0.085(6) 0.133(7) -0.044(5) 0.009(5) -0.011(5)
C26 0.051(4) 0.174(8) 0.077(5) 0.000(5) -0.021(4) 0.012(5)
C27 0.067(5) 0.185(9) 0.091(6) 0.035(5) -0.008(4) -0.014(5)

_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 C7 1.313(6) . ?
O1 C9 1.451(6) . ?
O2 C8 1.338(6) . ?
O2 C9 1.415(6) . ?
O3 C7 1.199(6) . ?
O4 C8 1.188(5) . ?
O5 C27 1.460(7) . ?
O5 C4 1.492(7) . ?
O6 C4 1.225(7) . ?
O6 C26 1.377(7) . ?
O7 C22 1.353(6) . ?
O7 C25 1.410(7) . ?
O8 C15 1.368(6) . ?
O8 C18 1.406(8) . ?
C1 C8 1.500(7) . ?
C1 C7 1.507(7) . ?
C1 C2 1.562(7) . ?
C1 C6 1.590(6) . ?
C2 C3 1.440(7) . ?
C2 C12 1.506(7) . ?
C2 H2 0.9800 . ?
C3 C4 1.605(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.570(8) . ?
C5 C6 1.428(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C19 1.512(7) . ?
C6 H6 0.9800 . ?
C9 C11 1.466(7) . ?
C9 C10 1.486(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.371(7) . ?
C12 C17 1.389(7) . ?
C13 C14 1.371(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(8) . ?
C16 C17 1.380(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.380(7) . ?
C19 C24 1.397(7) . ?
C20 C21 1.384(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(7) . ?
C23 C24 1.372(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.400(8) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?

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
C7 O1 C9 125.0(4) . . ?
C8 O2 C9 125.3(4) . . ?
C27 O5 C4 103.0(5) . . ?
C4 O6 C26 107.6(6) . . ?
C22 O7 C25 119.0(5) . . ?
C15 O8 C18 117.3(5) . . ?
C8 C1 C7 113.3(4) . . ?
C8 C1 C2 109.2(4) . . ?
C7 C1 C2 107.5(4) . . ?
C8 C1 C6 109.3(4) . . ?
C7 C1 C6 107.0(4) . . ?
C2 C1 C6 110.5(4) . . ?
C3 C2 C12 116.3(5) . . ?
C3 C2 C1 114.2(5) . . ?
C12 C2 C1 110.8(4) . . ?
C3 C2 H2 104.7 . . ?
C12 C2 H2 104.7 . . ?
C1 C2 H2 104.7 . . ?
C2 C3 C4 117.1(6) . . ?
C2 C3 H3A 108.0 . . ?
C4 C3 H3A 108.0 . . ?
C2 C3 H3B 108.0 . . ?
C4 C3 H3B 108.0 . . ?
H3A C3 H3B 107.3 . . ?
O6 C4 O5 112.6(6) . . ?
O6 C4 C5 113.2(6) . . ?
O5 C4 C5 106.5(5) . . ?
O6 C4 C3 113.4(6) . . ?
O5 C4 C3 104.8(5) . . ?
C5 C4 C3 105.6(5) . . ?
C6 C5 C4 116.8(5) . . ?
C6 C5 H5A 108.1 . . ?
C4 C5 H5A 108.1 . . ?
C6 C5 H5B 108.1 . . ?
C4 C5 H5B 108.1 . . ?
H5A C5 H5B 107.3 . . ?
C5 C6 C19 117.0(5) . . ?
C5 C6 C1 114.6(5) . . ?
C19 C6 C1 111.4(4) . . ?
C5 C6 H6 104.0 . . ?
C19 C6 H6 104.0 . . ?
C1 C6 H6 104.0 . . ?
O3 C7 O1 116.7(5) . . ?
O3 C7 C1 122.1(5) . . ?
O1 C7 C1 121.2(5) . . ?
O4 C8 O2 114.5(5) . . ?
O4 C8 C1 124.6(5) . . ?
O2 C8 C1 120.8(5) . . ?
O2 C9 O1 114.1(4) . . ?
O2 C9 C11 108.6(5) . . ?
O1 C9 C11 106.1(5) . . ?
O2 C9 C10 107.7(5) . . ?
O1 C9 C10 106.6(5) . . ?
C11 C9 C10 113.8(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 117.3(5) . . ?
C13 C12 C2 122.5(5) . . ?
C17 C12 C2 120.2(6) . . ?
C12 C13 C14 122.2(5) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C13 C14 C15 120.0(6) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
O8 C15 C16 115.9(6) . . ?
O8 C15 C14 125.3(6) . . ?
C16 C15 C14 118.8(6) . . ?
C15 C16 C17 120.7(6) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 120.9(6) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
O8 C18 H18A 109.5 . . ?
O8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 117.1(5) . . ?
C20 C19 C6 122.6(5) . . ?
C24 C19 C6 120.3(6) . . ?
C19 C20 C21 122.0(6) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C22 C21 C20 119.7(6) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
O7 C22 C21 115.8(6) . . ?
O7 C22 C23 124.9(6) . . ?
C21 C22 C23 119.3(6) . . ?
C24 C23 C22 120.7(6) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C19 121.1(6) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
O7 C25 H25A 109.5 . . ?
O7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O6 C26 C27 113.5(6) . . ?
O6 C26 H26A 108.9 . . ?
C27 C26 H26A 108.9 . . ?
O6 C26 H26B 108.9 . . ?
C27 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C26 C27 O5 102.1(5) . . ?
C26 C27 H27A 111.3 . . ?
O5 C27 H27A 111.3 . . ?
C26 C27 H27B 111.3 . . ?
O5 C27 H27B 111.3 . . ?
H27A C27 H27B 109.2 . . ?

_diffrn_measured_fraction_theta_max 0.935
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.050

# Attachment 'revised_4b.cif'

data_051227t
_database_code_depnum_ccdc_archive 'CCDC 658847'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H26 Br2 N0 O6'
_chemical_formula_weight         594.29

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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 '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                   7.356(3)
_cell_length_b                   12.590(5)
_cell_length_c                   14.852(6)
_cell_angle_alpha                69.787(6)
_cell_angle_beta                 87.415(7)
_cell_angle_gamma                79.243(6)
_cell_volume                     1267.8(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    920
_cell_measurement_theta_min      2.641
_cell_measurement_theta_max      25.314

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    3.236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5936
_exptl_absorpt_correction_T_max  0.7594
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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            6454
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_sigmaI/netI    0.1992
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4330
_reflns_number_gt                1413
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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          
;
Atom C25 is disordered over two sites, C25 and C25', for which occupation
factors were refined and converged to 0.320(18) and 0.680(18), respectively.
During refinement, atoms c25 and c25' are constrained to have the same x,
y and z parameters and anisotropic displacement parameters. Atom C26
is also disordered over two sites, C26 and C26' with occupation factors
0.320(18) and 0.680(18), respectively. All of the atoms of C, O, Br closer
than 3.8 \%A are restrained with an s. u. value of 0.02 \%A^2^ to have the
same U~ij~ components. If (according to the connectivity table, i.e.
ignoring attached hydrogens) one or both of the two atoms involved is
terminal (or not bonded at all), 0.04 is used instead as 0.02. The
distance between C24,C26 and C24, C26' are restrained to 2.54 \%A with
an estimated standard deviation 0.02. The distance of c25-c26, c24-c25
and c25-c26' are restrained to 1.53 \%A with an estimated standard
deviation 0.02. The distance of o5-c7, o5-c24, o6-c7, o6-c25 are
restrained to 1.43 \%A with an estimated standard deviation 0.02.
Atom Br2 is disordered over two sites, Br2 and Br2', for which
occupation factors were refined and converged to 0.51(4) and
0.49(4), respectively.
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^)+(0.0380P)^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         4330
_refine_ls_number_parameters     327
_refine_ls_number_restraints     1215
_refine_ls_R_factor_all          0.2196
_refine_ls_R_factor_gt           0.0728
_refine_ls_wR_factor_ref         0.1455
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.949
_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
Br1 Br -0.42012(15) 0.06501(8) 1.10942(7) 0.0968(5) Uani 1 1 d U . .
Br2 Br 0.153(4) 0.9617(10) 0.6351(8) 0.129(4) Uani 0.51(4) 1 d PU A 1
Br2' Br 0.052(4) 0.9718(7) 0.6478(10) 0.133(4) Uani 0.49(4) 1 d PU A 2
O1 O 0.0177(8) 0.4886(5) 0.8942(4) 0.0710(15) Uani 1 1 d U . .
O2 O -0.2101(7) 0.5229(5) 0.7764(4) 0.0800(16) Uani 1 1 d U . .
O3 O 0.2839(8) 0.3774(4) 0.9013(4) 0.0636(16) Uani 1 1 d U . .
O4 O -0.1776(7) 0.4473(4) 0.6644(4) 0.0771(17) Uani 1 1 d U . .
O5 O 0.2593(9) 0.2562(5) 0.5545(4) 0.1010(19) Uani 1 1 d DU C .
O6 O 0.4502(10) 0.2393(5) 0.6762(4) 0.0924(17) Uani 1 1 d DU . .
C1 C 0.1367(14) 0.4189(7) 0.8619(6) 0.057(2) Uani 1 1 d U . .
C2 C -0.1683(13) 0.5300(8) 0.8662(7) 0.067(2) Uani 1 1 d U . .
C3 C -0.1111(14) 0.4561(7) 0.7342(7) 0.068(2) Uani 1 1 d U . .
C4 C 0.0841(11) 0.4000(6) 0.7706(6) 0.0578(18) Uani 1 1 d U . .
C5 C 0.1176(11) 0.2655(6) 0.7948(5) 0.0652(19) Uani 1 1 d U C .
H5 H 0.2411 0.2357 0.8250 0.078 Uiso 1 1 calc R . .
C6 C 0.1253(13) 0.2337(7) 0.7058(6) 0.084(2) Uani 1 1 d U . .
H6A H 0.0047 0.2600 0.6740 0.100 Uiso 1 1 calc R C .
H6B H 0.1540 0.1505 0.7239 0.100 Uiso 1 1 calc R . .
C7 C 0.2707(14) 0.2862(7) 0.6355(7) 0.082(2) Uani 1 1 d DU C .
C8 C 0.2277(12) 0.4198(7) 0.6086(6) 0.081(2) Uani 1 1 d U . .
H8A H 0.3187 0.4532 0.5636 0.098 Uiso 1 1 calc R C .
H8B H 0.1068 0.4498 0.5772 0.098 Uiso 1 1 calc R . .
C9 C 0.2306(11) 0.4533(6) 0.6926(6) 0.069(2) Uani 1 1 d U C .
H9 H 0.3536 0.4200 0.7227 0.083 Uiso 1 1 calc R . .
C10 C -0.2069(13) 0.6528(7) 0.8562(6) 0.106(3) Uani 1 1 d U . .
H10A H -0.3337 0.6847 0.8365 0.158 Uiso 1 1 calc R . .
H10B H -0.1274 0.6932 0.8089 0.158 Uiso 1 1 calc R . .
H10C H -0.1845 0.6603 0.9167 0.158 Uiso 1 1 calc R . .
C11 C -0.2822(11) 0.4550(6) 0.9417(5) 0.076(2) Uani 1 1 d U . .
H11A H -0.4112 0.4804 0.9241 0.114 Uiso 1 1 calc R . .
H11B H -0.2618 0.4611 1.0029 0.114 Uiso 1 1 calc R . .
H11C H -0.2454 0.3763 0.9454 0.114 Uiso 1 1 calc R . .
C12 C -0.0149(12) 0.2112(6) 0.8688(6) 0.0561(19) Uani 1 1 d U . .
C13 C 0.0441(12) 0.1672(6) 0.9644(6) 0.068(2) Uani 1 1 d U C .
H13 H 0.1648 0.1672 0.9807 0.081 Uiso 1 1 calc R . .
C14 C -0.0782(13) 0.1233(6) 1.0353(6) 0.072(2) Uani 1 1 d U . .
H14 H -0.0391 0.0948 1.0993 0.087 Uiso 1 1 calc R C .
C15 C -0.2547(13) 0.1210(6) 1.0128(7) 0.064(2) Uani 1 1 d U C .
C16 C -0.3171(11) 0.1642(6) 0.9171(6) 0.067(2) Uani 1 1 d U . .
H16 H -0.4377 0.1640 0.9009 0.080 Uiso 1 1 calc R C .
C17 C -0.1928(13) 0.2069(6) 0.8477(6) 0.069(2) Uani 1 1 d U C .
H17 H -0.2311 0.2340 0.7836 0.083 Uiso 1 1 calc R . .
C18 C 0.2047(12) 0.5829(6) 0.6711(6) 0.061(2) Uani 1 1 d U . .
C19 C 0.3090(12) 0.6205(7) 0.7226(6) 0.078(2) Uani 1 1 d U C .
H19 H 0.4012 0.5686 0.7645 0.094 Uiso 1 1 calc R . .
C20 C 0.2792(13) 0.7354(7) 0.7134(6) 0.093(3) Uani 1 1 d U . .
H20 H 0.3513 0.7617 0.7481 0.111 Uiso 1 1 calc R C .
C21 C 0.1409(15) 0.8104(7) 0.6517(7) 0.085(3) Uani 1 1 d U A .
C22 C 0.0427(13) 0.7738(7) 0.5975(6) 0.081(2) Uani 1 1 d U . .
H22 H -0.0453 0.8257 0.5530 0.097 Uiso 1 1 calc R C .
C23 C 0.0739(12) 0.6600(7) 0.6087(6) 0.072(2) Uani 1 1 d U C .
H23 H 0.0037 0.6344 0.5725 0.086 Uiso 1 1 calc R . .
C24 C 0.4398(14) 0.2316(9) 0.5185(7) 0.130(3) Uani 1 1 d DU . .
H24A H 0.4661 0.2965 0.4645 0.156 Uiso 1 1 calc R B 1
H24B H 0.4542 0.1642 0.4994 0.156 Uiso 1 1 calc R B 1
C25 C 0.5598(15) 0.2100(9) 0.6036(8) 0.119(3) Uani 0.320(18) 1 d PDU C 1
H25 H 0.5957 0.2858 0.5774 0.142 Uiso 0.320(18) 1 calc PR C 1
C26 C 0.755(3) 0.147(3) 0.602(2) 0.160(9) Uani 0.320(18) 1 d PDU C 1
H26A H 0.8223 0.1402 0.6583 0.240 Uiso 0.320(18) 1 calc PR C 1
H26B H 0.8157 0.1889 0.5459 0.240 Uiso 0.320(18) 1 calc PR C 1
H26C H 0.7525 0.0714 0.6009 0.240 Uiso 0.320(18) 1 calc PR C 1
C25' C 0.5598(15) 0.2100(9) 0.6036(8) 0.119(3) Uani 0.680(18) 1 d PU C 2
H25' H 0.6610 0.2537 0.5858 0.142 Uiso 0.680(18) 1 calc PR C 2
C26' C 0.633(3) 0.0856(14) 0.6492(12) 0.201(8) Uani 0.680(18) 1 d PDU C 2
H26D H 0.6963 0.0725 0.7082 0.302 Uiso 0.680(18) 1 calc PR C 2
H26E H 0.7168 0.0596 0.6068 0.302 Uiso 0.680(18) 1 calc PR C 2
H26F H 0.5318 0.0441 0.6624 0.302 Uiso 0.680(18) 1 calc PR C 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
Br1 0.0912(9) 0.0934(8) 0.1038(8) -0.0232(6) 0.0252(6) -0.0385(6)
Br2 0.173(10) 0.061(2) 0.150(3) -0.030(2) -0.045(5) -0.016(4)
Br2' 0.173(10) 0.047(2) 0.170(4) -0.027(2) -0.049(6) -0.003(4)
O1 0.065(4) 0.081(3) 0.077(3) -0.048(3) -0.006(3) 0.006(3)
O2 0.070(4) 0.094(3) 0.079(3) -0.047(3) -0.007(3) 0.013(3)
O3 0.058(4) 0.055(3) 0.076(4) -0.022(3) -0.012(3) -0.003(3)
O4 0.070(4) 0.078(4) 0.084(4) -0.032(3) -0.025(3) -0.002(3)
O5 0.110(4) 0.106(4) 0.085(4) -0.043(3) 0.006(3) 0.006(3)
O6 0.106(4) 0.095(4) 0.086(4) -0.049(3) 0.007(3) -0.005(3)
C1 0.059(4) 0.055(4) 0.066(4) -0.028(3) 0.003(4) -0.015(4)
C2 0.059(5) 0.078(5) 0.072(5) -0.042(4) -0.022(5) 0.008(5)
C3 0.075(4) 0.060(4) 0.074(4) -0.027(4) -0.005(4) -0.017(4)
C4 0.059(4) 0.054(3) 0.069(4) -0.031(3) 0.003(3) -0.012(3)
C5 0.073(4) 0.062(4) 0.072(4) -0.037(3) 0.004(4) -0.014(3)
C6 0.095(4) 0.070(4) 0.087(4) -0.032(4) 0.002(4) -0.008(4)
C7 0.094(5) 0.081(4) 0.078(5) -0.046(4) 0.005(4) 0.001(4)
C8 0.090(4) 0.077(4) 0.078(4) -0.028(4) 0.001(4) -0.016(4)
C9 0.080(4) 0.060(4) 0.074(4) -0.028(3) 0.006(4) -0.018(3)
C10 0.107(7) 0.088(6) 0.116(7) -0.044(6) -0.015(6) 0.019(6)
C11 0.067(6) 0.090(6) 0.082(6) -0.045(5) -0.002(5) -0.012(5)
C12 0.055(4) 0.054(4) 0.072(4) -0.035(3) 0.001(4) -0.016(4)
C13 0.063(5) 0.061(4) 0.080(5) -0.024(4) 0.002(4) -0.015(4)
C14 0.074(6) 0.062(4) 0.082(5) -0.024(4) 0.003(5) -0.016(4)
C15 0.063(5) 0.056(4) 0.079(5) -0.026(4) 0.004(5) -0.024(4)
C16 0.057(5) 0.066(5) 0.089(6) -0.028(4) 0.003(5) -0.034(4)
C17 0.081(5) 0.061(4) 0.071(4) -0.027(4) -0.007(4) -0.016(4)
C18 0.072(4) 0.053(4) 0.064(4) -0.026(3) -0.003(4) -0.016(4)
C19 0.085(5) 0.064(4) 0.089(5) -0.021(4) -0.012(4) -0.027(4)
C20 0.108(6) 0.064(5) 0.104(5) -0.017(5) -0.037(5) -0.025(5)
C21 0.106(6) 0.045(4) 0.101(6) -0.013(4) -0.022(5) -0.021(5)
C22 0.098(6) 0.049(4) 0.088(5) -0.011(4) -0.030(5) -0.010(4)
C23 0.083(5) 0.057(4) 0.075(4) -0.016(4) -0.009(4) -0.021(4)
C24 0.113(6) 0.148(6) 0.118(6) -0.044(5) 0.001(6) 0.004(6)
C25 0.106(5) 0.123(5) 0.106(5) -0.037(4) 0.010(4) 0.021(5)
C26 0.156(15) 0.138(14) 0.150(14) -0.026(13) 0.011(14) 0.013(14)
C25' 0.106(5) 0.123(5) 0.106(5) -0.037(4) 0.010(4) 0.021(5)
C26' 0.179(13) 0.184(12) 0.180(12) -0.011(11) 0.044(11) 0.009(11)

_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
Br1 C15 1.870(8) . ?
Br2 C21 1.853(12) . ?
Br2' C21 1.997(15) . ?
O1 C1 1.316(9) . ?
O1 C2 1.397(9) . ?
O2 C3 1.313(9) . ?
O2 C2 1.419(8) . ?
O3 C1 1.193(9) . ?
O4 C3 1.213(9) . ?
O5 C7 1.390(8) . ?
O5 C24 1.428(9) . ?
O6 C7 1.411(9) . ?
O6 C25 1.426(9) . ?
C1 C4 1.534(10) . ?
C2 C10 1.475(10) . ?
C2 C11 1.525(10) . ?
C3 C4 1.510(11) . ?
C4 C5 1.577(9) . ?
C4 C9 1.604(9) . ?
C5 C12 1.503(9) . ?
C5 C6 1.504(9) . ?
C5 H5 0.9800 . ?
C6 C7 1.535(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.562(10) . ?
C8 C9 1.450(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C18 1.526(9) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.374(10) . ?
C12 C13 1.391(10) . ?
C13 C14 1.386(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.400(10) . ?
C16 C17 1.380(9) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.355(10) . ?
C18 C19 1.356(10) . ?
C19 C20 1.381(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.347(10) . ?
C22 C23 1.360(10) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.492(10) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.512(16) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26' H26D 0.9600 . ?
C26' H26E 0.9600 . ?
C26' H26F 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
C1 O1 C2 126.5(8) . . ?
C3 O2 C2 126.0(7) . . ?
C7 O5 C24 110.3(8) . . ?
C7 O6 C25 105.9(8) . . ?
O3 C1 O1 119.5(9) . . ?
O3 C1 C4 122.3(9) . . ?
O1 C1 C4 118.1(8) . . ?
O1 C2 O2 113.3(7) . . ?
O1 C2 C10 106.9(8) . . ?
O2 C2 C10 107.4(7) . . ?
O1 C2 C11 107.3(7) . . ?
O2 C2 C11 107.5(7) . . ?
C10 C2 C11 114.8(8) . . ?
O4 C3 O2 118.2(10) . . ?
O4 C3 C4 122.9(9) . . ?
O2 C3 C4 118.8(9) . . ?
C3 C4 C1 114.0(8) . . ?
C3 C4 C5 111.8(7) . . ?
C1 C4 C5 106.2(6) . . ?
C3 C4 C9 110.4(7) . . ?
C1 C4 C9 104.9(6) . . ?
C5 C4 C9 109.2(6) . . ?
C12 C5 C6 114.8(6) . . ?
C12 C5 C4 111.2(6) . . ?
C6 C5 C4 112.0(6) . . ?
C12 C5 H5 106.0 . . ?
C6 C5 H5 106.0 . . ?
C4 C5 H5 106.0 . . ?
C5 C6 C7 112.4(7) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
O5 C7 O6 108.0(7) . . ?
O5 C7 C6 107.4(8) . . ?
O6 C7 C6 110.3(8) . . ?
O5 C7 C8 110.5(7) . . ?
O6 C7 C8 111.3(8) . . ?
C6 C7 C8 109.1(7) . . ?
C9 C8 C7 111.6(7) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C18 114.6(7) . . ?
C8 C9 C4 112.0(6) . . ?
C18 C9 C4 109.8(6) . . ?
C8 C9 H9 106.6 . . ?
C18 C9 H9 106.6 . . ?
C4 C9 H9 106.6 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.4(8) . . ?
C17 C12 C5 123.7(8) . . ?
C13 C12 C5 117.8(8) . . ?
C14 C13 C12 119.5(8) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 121.1(9) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.5(8) . . ?
C14 C15 Br1 120.7(8) . . ?
C16 C15 Br1 118.8(7) . . ?
C17 C16 C15 117.4(8) . . ?
C17 C16 H16 121.3 . . ?
C15 C16 H16 121.3 . . ?
C12 C17 C16 123.0(9) . . ?
C12 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?
C23 C18 C19 119.1(8) . . ?
C23 C18 C9 123.1(8) . . ?
C19 C18 C9 117.7(8) . . ?
C18 C19 C20 120.4(9) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 118.7(9) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C22 C21 C20 120.7(8) . . ?
C22 C21 Br2 126.7(9) . . ?
C20 C21 Br2 111.0(10) . . ?
C22 C21 Br2' 115.6(9) . . ?
C20 C21 Br2' 123.3(9) . . ?
Br2 C21 Br2' 22.3(3) . . ?
C21 C22 C23 119.1(9) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C18 C23 C22 121.8(9) . . ?
C18 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
O5 C24 C25 101.7(8) . . ?
O5 C24 H24A 111.4 . . ?
C25 C24 H24A 111.4 . . ?
O5 C24 H24B 111.4 . . ?
C25 C24 H24B 111.4 . . ?
H24A C24 H24B 109.3 . . ?
O6 C25 C24 109.5(9) . . ?
O6 C25 C26 133.7(15) . . ?
C24 C25 C26 116.0(13) . . ?
O6 C25 H25 93.0 . . ?
C24 C25 H25 93.0 . . ?
C26 C25 H25 93.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H26D C26' H26E 109.5 . . ?
H26D C26' H26F 109.5 . . ?
H26E C26' H26F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.073


# Attachment '2h.cif'

data_070710b
_database_code_depnum_ccdc_archive 'CCDC 700773'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 O9'
_chemical_formula_weight         466.43

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)/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                   6.8061(8)
_cell_length_b                   22.230(3)
_cell_length_c                   14.9656(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.243(2)
_cell_angle_gamma                90.00
_cell_volume                     2234.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    968
_cell_measurement_theta_min      2.758
_cell_measurement_theta_max      28.178

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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            10899
_diffrn_reflns_av_R_equivalents  0.1540
_diffrn_reflns_av_sigmaI/netI    0.1757
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3836
_reflns_number_gt                1025
_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^)+(0.0859P)^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         3836
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3029
_refine_ls_R_factor_gt           0.0943
_refine_ls_wR_factor_ref         0.2599
_refine_ls_wR_factor_gt          0.1917
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.0718(7) 0.6207(3) 0.7673(3) 0.0880(16) Uani 1 1 d . A .
O2 O 0.3483(10) 0.5555(3) 0.7770(4) 0.0982(17) Uani 1 1 d . A .
O3 O 0.158(3) 0.7248(8) 0.7922(14) 0.087(3) Uani 0.502(14) 1 d P A 1
O4 O 0.657(2) 0.6131(7) 0.8201(10) 0.081(3) Uani 0.414(10) 1 d P A 1
O3' O 0.048(3) 0.7099(8) 0.7738(14) 0.087(3) Uani 0.498(14) 1 d P A 2
O4' O 0.6480(16) 0.5700(5) 0.8171(7) 0.081(3) Uani 0.586(10) 1 d P A 2
O5 O 0.7268(9) 0.8220(3) 0.8259(4) 0.115(2) Uani 1 1 d . . .
O6 O 0.0137(10) 0.6728(2) 1.1060(4) 0.1146(19) Uani 1 1 d . . .
O7 O 0.1819(9) 0.5932(3) 1.1848(3) 0.1008(18) Uani 1 1 d . A .
O8 O 0.6138(10) 0.5650(3) 0.4665(6) 0.130(2) Uani 1 1 d . . .
O9 O 0.2856(11) 0.5763(3) 0.3894(4) 0.125(2) Uani 1 1 d . A .
C1 C 0.1828(16) 0.6695(5) 0.7844(5) 0.087(2) Uani 1 1 d . . .
C2 C 0.4121(14) 0.6639(4) 0.8016(5) 0.087(3) Uani 1 1 d . A .
C3 C 0.4782(16) 0.5971(5) 0.8031(5) 0.088(3) Uani 1 1 d . . .
C4 C 0.1442(12) 0.5597(3) 0.7819(6) 0.076(2) Uani 1 1 d . . .
C5 C 0.1036(10) 0.5394(3) 0.8727(5) 0.092(2) Uani 1 1 d . A .
H5A H 0.1527 0.4992 0.8841 0.138 Uiso 1 1 calc R . .
H5B H -0.0372 0.5401 0.8733 0.138 Uiso 1 1 calc R . .
H5C H 0.1693 0.5658 0.9187 0.138 Uiso 1 1 calc R . .
C6 C 0.0438(14) 0.5244(4) 0.7046(6) 0.138(4) Uani 1 1 d . A .
H6A H 0.0615 0.5438 0.6491 0.208 Uiso 1 1 calc R . .
H6B H -0.0957 0.5217 0.7077 0.208 Uiso 1 1 calc R . .
H6C H 0.1001 0.4848 0.7065 0.208 Uiso 1 1 calc R . .
C7 C 0.536(4) 0.6794(12) 0.8962(15) 0.091(6) Uani 0.58(2) 1 d P A 1
H7 H 0.6663 0.6594 0.9050 0.109 Uiso 0.58(2) 1 calc PR A 1
C8 C 0.558(9) 0.748(4) 0.900(6) 0.090(14) Uani 0.58(2) 1 d P A 1
H8A H 0.4290 0.7655 0.9022 0.108 Uiso 0.58(2) 1 calc PR A 1
H8B H 0.6458 0.7586 0.9551 0.108 Uiso 0.58(2) 1 calc PR A 1
C7' C 0.428(6) 0.7048(17) 0.888(2) 0.091(6) Uani 0.42(2) 1 d P A 2
H7' H 0.3176 0.7335 0.8802 0.109 Uiso 0.42(2) 1 calc PR A 2
C8' C 0.625(14) 0.739(6) 0.902(8) 0.090(14) Uani 0.42(2) 1 d P A 2
H8'1 H 0.6313 0.7657 0.9539 0.108 Uiso 0.42(2) 1 calc PR A 2
H8'2 H 0.7355 0.7111 0.9137 0.108 Uiso 0.42(2) 1 calc PR A 2
C9 C 0.6403(13) 0.7749(4) 0.8199(6) 0.095(3) Uani 1 1 d . . .
C10 C 0.537(7) 0.750(3) 0.731(5) 0.089(12) Uani 0.56(2) 1 d P A 1
H10A H 0.6014 0.7661 0.6826 0.106 Uiso 0.56(2) 1 calc PR A 1
H10B H 0.3999 0.7644 0.7207 0.106 Uiso 0.56(2) 1 calc PR A 1
C11 C 0.538(4) 0.6816(12) 0.7276(17) 0.085(5) Uani 0.56(2) 1 d P A 1
H11 H 0.6739 0.6654 0.7407 0.102 Uiso 0.56(2) 1 calc PR A 1
C10' C 0.622(9) 0.739(4) 0.731(7) 0.087(15) Uani 0.44(2) 1 d P A 2
H10C H 0.6248 0.7667 0.6810 0.104 Uiso 0.44(2) 1 calc PR A 2
H10D H 0.7342 0.7120 0.7336 0.104 Uiso 0.44(2) 1 calc PR A 2
C11' C 0.427(6) 0.7034(16) 0.716(2) 0.085(5) Uani 0.44(2) 1 d P A 2
H11' H 0.3142 0.7312 0.7052 0.102 Uiso 0.44(2) 1 calc PR A 2
C12 C 0.4219(17) 0.6659(5) 0.9747(6) 0.103(3) Uani 1 1 d . . .
C13 C 0.2424(16) 0.6862(4) 0.9963(6) 0.101(3) Uani 1 1 d . A .
H13 H 0.1712 0.7169 0.9635 0.121 Uiso 1 1 calc R . .
C14 C 0.1733(17) 0.6591(5) 1.0685(7) 0.097(3) Uani 1 1 d . . .
C15 C 0.2695(16) 0.6131(5) 1.1163(6) 0.095(3) Uani 1 1 d . A .
C16 C 0.4451(15) 0.5895(5) 1.0977(6) 0.114(3) Uani 1 1 d . . .
H16 H 0.5130 0.5581 1.1303 0.136 Uiso 1 1 calc R A .
C17 C 0.5129(15) 0.6185(5) 1.0219(7) 0.117(3) Uani 1 1 d . A .
H17 H 0.6281 0.6037 1.0039 0.141 Uiso 1 1 calc R . .
C18 C 0.0290(15) 0.6370(5) 1.1881(6) 0.117(3) Uani 1 1 d . . .
H18A H 0.0628 0.6624 1.2411 0.140 Uiso 1 1 calc R A .
H18B H -0.0968 0.6172 1.1914 0.140 Uiso 1 1 calc R . .
C19 C 0.4331(18) 0.6647(4) 0.6309(6) 0.092(3) Uani 1 1 d . . .
C20 C 0.5683(14) 0.6282(4) 0.5948(6) 0.094(3) Uani 1 1 d . A .
H20 H 0.6971 0.6227 0.6255 0.113 Uiso 1 1 calc R . .
C21 C 0.5066(18) 0.6007(4) 0.5133(7) 0.090(3) Uani 1 1 d . . .
C22 C 0.3167(18) 0.6083(4) 0.4683(6) 0.087(3) Uani 1 1 d . A .
C23 C 0.1716(16) 0.6434(4) 0.4979(7) 0.108(3) Uani 1 1 d . . .
H23 H 0.0436 0.6492 0.4664 0.130 Uiso 1 1 calc R A .
C24 C 0.2470(17) 0.6692(3) 0.5832(7) 0.096(3) Uani 1 1 d . A .
H24 H 0.1574 0.6920 0.6097 0.116 Uiso 1 1 calc R . .
C25 C 0.482(2) 0.5523(4) 0.3817(7) 0.126(3) Uani 1 1 d . . .
H25A H 0.4741 0.5093 0.3709 0.152 Uiso 1 1 calc R A .
H25B H 0.5325 0.5713 0.3316 0.152 Uiso 1 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 0.060(3) 0.077(5) 0.127(4) 0.016(3) 0.013(3) 0.003(3)
O2 0.085(5) 0.081(4) 0.132(5) 0.008(3) 0.029(4) 0.012(4)
O3 0.100(12) 0.050(7) 0.113(8) -0.007(6) 0.027(10) -0.007(7)
O4 0.053(4) 0.078(8) 0.113(5) 0.006(7) 0.019(4) -0.003(7)
O3' 0.100(12) 0.050(7) 0.113(8) -0.007(6) 0.027(10) -0.007(7)
O4' 0.053(4) 0.078(8) 0.113(5) 0.006(7) 0.019(4) -0.003(7)
O5 0.136(5) 0.078(4) 0.141(5) -0.019(3) 0.055(4) -0.049(4)
O6 0.150(6) 0.099(5) 0.102(4) 0.006(4) 0.042(4) 0.006(4)
O7 0.128(5) 0.100(5) 0.084(4) 0.001(3) 0.046(3) 0.005(4)
O8 0.138(6) 0.128(6) 0.125(6) 0.002(4) 0.019(5) 0.003(5)
O9 0.130(6) 0.147(6) 0.096(5) -0.019(4) 0.010(4) -0.015(5)
C1 0.113(9) 0.071(7) 0.085(6) 0.010(5) 0.041(5) -0.002(6)
C2 0.102(7) 0.090(7) 0.078(6) -0.008(5) 0.036(5) -0.049(6)
C3 0.070(7) 0.118(9) 0.082(6) 0.004(6) 0.028(5) -0.013(7)
C4 0.064(6) 0.049(5) 0.116(7) -0.004(5) 0.017(5) -0.017(4)
C5 0.089(6) 0.079(6) 0.109(6) -0.002(5) 0.022(5) -0.011(4)
C6 0.160(9) 0.126(8) 0.125(8) -0.016(6) 0.006(6) -0.068(7)
C7 0.096(19) 0.093(19) 0.091(9) -0.005(11) 0.034(14) -0.020(10)
C8 0.10(4) 0.08(3) 0.088(8) 0.003(14) 0.03(3) -0.02(3)
C7' 0.096(19) 0.093(19) 0.091(9) -0.005(11) 0.034(14) -0.020(10)
C8' 0.10(4) 0.08(3) 0.088(8) 0.003(14) 0.03(3) -0.02(3)
C9 0.104(7) 0.071(7) 0.113(7) -0.013(6) 0.025(6) -0.029(5)
C10 0.11(4) 0.08(3) 0.086(15) 0.019(15) 0.03(3) -0.02(3)
C11 0.093(19) 0.079(17) 0.090(10) -0.001(10) 0.036(16) -0.020(11)
C10' 0.10(4) 0.08(4) 0.085(18) 0.01(2) 0.03(4) -0.03(3)
C11' 0.093(19) 0.079(17) 0.090(10) -0.001(10) 0.036(16) -0.020(11)
C12 0.118(9) 0.109(9) 0.092(7) -0.017(6) 0.047(7) -0.055(7)
C13 0.141(9) 0.082(7) 0.082(6) -0.019(5) 0.026(6) -0.034(6)
C14 0.131(9) 0.092(8) 0.081(6) -0.025(6) 0.052(6) -0.030(7)
C15 0.102(8) 0.115(9) 0.072(6) -0.010(6) 0.025(6) -0.015(7)
C16 0.107(8) 0.145(9) 0.095(7) -0.020(6) 0.038(6) -0.020(7)
C17 0.108(8) 0.145(11) 0.103(8) -0.020(7) 0.027(6) -0.039(7)
C18 0.155(9) 0.116(8) 0.087(7) -0.012(6) 0.046(6) -0.021(7)
C19 0.115(9) 0.082(7) 0.082(7) -0.005(5) 0.027(7) -0.046(6)
C20 0.105(8) 0.102(7) 0.077(6) 0.008(5) 0.017(6) -0.037(6)
C21 0.116(9) 0.083(7) 0.073(7) -0.001(5) 0.026(7) -0.007(6)
C22 0.117(9) 0.082(7) 0.061(6) 0.002(5) 0.012(6) -0.016(6)
C23 0.145(9) 0.103(7) 0.085(7) 0.017(6) 0.044(7) -0.001(7)
C24 0.128(9) 0.073(6) 0.097(8) 0.014(5) 0.044(7) 0.000(6)
C25 0.171(11) 0.111(8) 0.098(8) -0.003(6) 0.025(8) -0.017(8)

_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 1.324(9) . ?
O1 C4 1.446(8) . ?
O2 C3 1.295(9) . ?
O2 C4 1.406(8) . ?
O3 C1 1.249(19) . ?
O4 C3 1.255(17) . ?
O3' C1 1.28(2) . ?
O4' C3 1.289(12) . ?
O5 C9 1.198(8) . ?
O6 C14 1.335(9) . ?
O6 C18 1.454(8) . ?
O7 C15 1.341(9) . ?
O7 C18 1.432(9) . ?
O8 C21 1.349(9) . ?
O8 C25 1.458(10) . ?
O9 C22 1.366(9) . ?
O9 C25 1.461(10) . ?
C1 C2 1.546(11) . ?
C2 C3 1.551(11) . ?
C2 C11 1.56(2) . ?
C2 C7 1.57(2) . ?
C2 C7' 1.57(4) . ?
C2 C11' 1.57(3) . ?
C4 C6 1.473(9) . ?
C4 C5 1.499(9) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.53(9) . ?
C7 C12 1.54(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.52(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7' C8' 1.53(13) . ?
C7' C12 1.57(3) . ?
C7' H7' 0.9800 . ?
C8' C9 1.48(13) . ?
C8' H8'1 0.9700 . ?
C8' H8'2 0.9700 . ?
C9 C10 1.50(8) . ?
C9 C10' 1.53(10) . ?
C10 C11 1.53(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C19 1.56(3) . ?
C11 H11 0.9800 . ?
C10' C11' 1.53(10) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C11' C19 1.55(4) . ?
C11' H11' 0.9800 . ?
C12 C17 1.361(11) . ?
C12 C13 1.388(11) . ?
C13 C14 1.384(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.355(11) . ?
C15 C16 1.374(11) . ?
C16 C17 1.443(12) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.354(11) . ?
C19 C20 1.398(11) . ?
C20 C21 1.368(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(11) . ?
C22 C23 1.386(11) . ?
C23 C24 1.418(11) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?

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 C4 124.7(7) . . ?
C3 O2 C4 124.7(7) . . ?
C14 O6 C18 106.1(8) . . ?
C15 O7 C18 102.6(7) . . ?
C21 O8 C25 104.9(8) . . ?
C22 O9 C25 103.9(7) . . ?
O3 C1 O3' 38.0(7) . . ?
O3 C1 O1 137.9(12) . . ?
O3' C1 O1 100.1(10) . . ?
O3 C1 C2 102.3(11) . . ?
O3' C1 C2 139.9(12) . . ?
O1 C1 C2 119.7(8) . . ?
C1 C2 C3 111.2(7) . . ?
C1 C2 C11 121.3(13) . . ?
C3 C2 C11 93.5(12) . . ?
C1 C2 C7 121.1(12) . . ?
C3 C2 C7 94.9(13) . . ?
C11 C2 C7 107.9(14) . . ?
C1 C2 C7' 91.4(16) . . ?
C3 C2 C7' 124.1(16) . . ?
C11 C2 C7' 117.7(17) . . ?
C7 C2 C7' 34.1(10) . . ?
C1 C2 C11' 91.0(15) . . ?
C3 C2 C11' 119.4(15) . . ?
C11 C2 C11' 33.1(9) . . ?
C7 C2 C11' 121.1(17) . . ?
C7' C2 C11' 110.0(19) . . ?
O4 C3 O4' 44.3(6) . . ?
O4 C3 O2 149.0(12) . . ?
O4' C3 O2 105.5(10) . . ?
O4 C3 C2 90.1(10) . . ?
O4' C3 C2 134.4(10) . . ?
O2 C3 C2 119.8(8) . . ?
O2 C4 O1 111.8(6) . . ?
O2 C4 C6 105.1(7) . . ?
O1 C4 C6 106.1(7) . . ?
O2 C4 C5 110.8(7) . . ?
O1 C4 C5 108.1(6) . . ?
C6 C4 C5 114.9(7) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 103(3) . . ?
C8 C7 C2 107(4) . . ?
C12 C7 C2 112.4(16) . . ?
C8 C7 H7 111.5 . . ?
C12 C7 H7 111.5 . . ?
C2 C7 H7 111.5 . . ?
C9 C8 C7 114(5) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8' C7' C12 108(5) . . ?
C8' C7' C2 110(5) . . ?
C12 C7' C2 111(2) . . ?
C8' C7' H7' 109.3 . . ?
C12 C7' H7' 109.3 . . ?
C2 C7' H7' 109.3 . . ?
C9 C8' C7' 109(7) . . ?
C9 C8' H8'1 109.8 . . ?
C7' C8' H8'1 109.8 . . ?
C9 C8' H8'2 109.8 . . ?
C7' C8' H8'2 109.8 . . ?
H8'1 C8' H8'2 108.3 . . ?
O5 C9 C8' 120(5) . . ?
O5 C9 C10 123(3) . . ?
C8' C9 C10 117(6) . . ?
O5 C9 C8 122(4) . . ?
C8' C9 C8 19(5) . . ?
C10 C9 C8 112(4) . . ?
O5 C9 C10' 119(4) . . ?
C8' C9 C10' 116(6) . . ?
C10 C9 C10' 24(3) . . ?
C8 C9 C10' 119(5) . . ?
C9 C10 C11 113(4) . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C19 106(3) . . ?
C10 C11 C2 103(3) . . ?
C19 C11 C2 112.1(17) . . ?
C10 C11 H11 112.0 . . ?
C19 C11 H11 112.0 . . ?
C2 C11 H11 112.0 . . ?
C11' C10' C9 110(5) . . ?
C11' C10' H10C 109.7 . . ?
C9 C10' H10C 109.7 . . ?
C11' C10' H10D 109.7 . . ?
C9 C10' H10D 109.7 . . ?
H10C C10' H10D 108.2 . . ?
C10' C11' C19 106(4) . . ?
C10' C11' C2 110(4) . . ?
C19 C11' C2 112(2) . . ?
C10' C11' H11' 109.6 . . ?
C19 C11' H11' 109.6 . . ?
C2 C11' H11' 109.6 . . ?
C17 C12 C13 118.3(9) . . ?
C17 C12 C7 107.6(15) . . ?
C13 C12 C7 133.3(15) . . ?
C17 C12 C7' 141.8(18) . . ?
C13 C12 C7' 99.1(17) . . ?
C7 C12 C7' 34.4(10) . . ?
C14 C13 C12 117.5(10) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
O6 C14 C15 107.9(9) . . ?
O6 C14 C13 129.0(12) . . ?
C15 C14 C13 123.0(11) . . ?
O7 C15 C14 114.5(10) . . ?
O7 C15 C16 122.5(11) . . ?
C14 C15 C16 122.9(10) . . ?
C15 C16 C17 112.7(10) . . ?
C15 C16 H16 123.6 . . ?
C17 C16 H16 123.6 . . ?
C12 C17 C16 125.3(10) . . ?
C12 C17 H17 117.3 . . ?
C16 C17 H17 117.3 . . ?
O7 C18 O6 107.2(6) . . ?
O7 C18 H18A 110.3 . . ?
O6 C18 H18A 110.3 . . ?
O7 C18 H18B 110.3 . . ?
O6 C18 H18B 110.3 . . ?
H18A C18 H18B 108.5 . . ?
C24 C19 C20 117.2(9) . . ?
C24 C19 C11' 104.4(18) . . ?
C20 C19 C11' 138.4(18) . . ?
C24 C19 C11 136.5(15) . . ?
C20 C19 C11 105.5(14) . . ?
C11' C19 C11 33.4(10) . . ?
C21 C20 C19 118.4(9) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
O8 C21 C20 127.7(12) . . ?
O8 C21 C22 111.3(9) . . ?
C20 C21 C22 120.9(10) . . ?
O9 C22 C21 111.4(10) . . ?
O9 C22 C23 123.4(11) . . ?
C21 C22 C23 125.3(10) . . ?
C22 C23 C24 110.0(9) . . ?
C22 C23 H23 125.0 . . ?
C24 C23 H23 125.0 . . ?
C19 C24 C23 128.1(9) . . ?
C19 C24 H24 115.9 . . ?
C23 C24 H24 115.9 . . ?
O8 C25 O9 107.7(7) . . ?
O8 C25 H25A 110.2 . . ?
O9 C25 H25A 110.2 . . ?
O8 C25 H25B 110.2 . . ?
O9 C25 H25B 110.2 . . ?
H25A C25 H25B 108.5 . . ?

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
C4 O1 C1 O3 -165.8(16) . . . . ?
C4 O1 C1 O3' -170.8(11) . . . . ?
C4 O1 C1 C2 14.0(10) . . . . ?
O3 C1 C2 C3 175.2(11) . . . . ?
O3' C1 C2 C3 -177.3(16) . . . . ?
O1 C1 C2 C3 -4.6(9) . . . . ?
O3 C1 C2 C11 -76.5(17) . . . . ?
O3' C1 C2 C11 -69(2) . . . . ?
O1 C1 C2 C11 103.7(14) . . . . ?
O3 C1 C2 C7 65.4(17) . . . . ?
O3' C1 C2 C7 73(2) . . . . ?
O1 C1 C2 C7 -114.5(13) . . . . ?
O3 C1 C2 C7' 47.5(17) . . . . ?
O3' C1 C2 C7' 55(2) . . . . ?
O1 C1 C2 C7' -132.3(14) . . . . ?
O3 C1 C2 C11' -62.5(18) . . . . ?
O3' C1 C2 C11' -55(2) . . . . ?
O1 C1 C2 C11' 117.7(15) . . . . ?
C4 O2 C3 O4 170.0(18) . . . . ?
C4 O2 C3 O4' 158.7(8) . . . . ?
C4 O2 C3 C2 -27.6(10) . . . . ?
C1 C2 C3 O4 -178.2(9) . . . . ?
C11 C2 C3 O4 56.1(14) . . . . ?
C7 C2 C3 O4 -52.2(12) . . . . ?
C7' C2 C3 O4 -71.0(19) . . . . ?
C11' C2 C3 O4 77.9(19) . . . . ?
C1 C2 C3 O4' -177.7(10) . . . . ?
C11 C2 C3 O4' 56.7(15) . . . . ?
C7 C2 C3 O4' -51.6(14) . . . . ?
C7' C2 C3 O4' -70(2) . . . . ?
C11' C2 C3 O4' 78(2) . . . . ?
C1 C2 C3 O2 10.7(9) . . . . ?
C11 C2 C3 O2 -114.9(12) . . . . ?
C7 C2 C3 O2 136.8(10) . . . . ?
C7' C2 C3 O2 118.0(18) . . . . ?
C11' C2 C3 O2 -93.2(18) . . . . ?
C3 O2 C4 O1 33.9(10) . . . . ?
C3 O2 C4 C6 148.5(8) . . . . ?
C3 O2 C4 C5 -86.8(9) . . . . ?
C1 O1 C4 O2 -26.5(10) . . . . ?
C1 O1 C4 C6 -140.5(7) . . . . ?
C1 O1 C4 C5 95.7(8) . . . . ?
C1 C2 C7 C8 -81(3) . . . . ?
C3 C2 C7 C8 161(3) . . . . ?
C11 C2 C7 C8 66(3) . . . . ?
C7' C2 C7 C8 -48(4) . . . . ?
C11' C2 C7 C8 32(4) . . . . ?
C1 C2 C7 C12 31(2) . . . . ?
C3 C2 C7 C12 -87.0(18) . . . . ?
C11 C2 C7 C12 177.8(17) . . . . ?
C7' C2 C7 C12 65(3) . . . . ?
C11' C2 C7 C12 144(2) . . . . ?
C12 C7 C8 C9 -171(3) . . . . ?
C2 C7 C8 C9 -53(5) . . . . ?
C1 C2 C7' C8' -150(6) . . . . ?
C3 C2 C7' C8' 93(5) . . . . ?
C11 C2 C7' C8' -23(6) . . . . ?
C7 C2 C7' C8' 58(6) . . . . ?
C11' C2 C7' C8' -59(6) . . . . ?
C1 C2 C7' C12 91(2) . . . . ?
C3 C2 C7' C12 -26(3) . . . . ?
C11 C2 C7' C12 -142(2) . . . . ?
C7 C2 C7' C12 -61(3) . . . . ?
C11' C2 C7' C12 -178(2) . . . . ?
C12 C7' C8' C9 178(5) . . . . ?
C2 C7' C8' C9 57(8) . . . . ?
C7' C8' C9 O5 148(5) . . . . ?
C7' C8' C9 C10 -30(8) . . . . ?
C7' C8' C9 C8 48(22) . . . . ?
C7' C8' C9 C10' -57(8) . . . . ?
C7 C8 C9 O5 -155(4) . . . . ?
C7 C8 C9 C8' -63(24) . . . . ?
C7 C8 C9 C10 47(5) . . . . ?
C7 C8 C9 C10' 22(6) . . . . ?
O5 C9 C10 C11 148(3) . . . . ?
C8' C9 C10 C11 -34(6) . . . . ?
C8 C9 C10 C11 -54(4) . . . . ?
C10' C9 C10 C11 59(13) . . . . ?
C9 C10 C11 C19 -178(2) . . . . ?
C9 C10 C11 C2 64(4) . . . . ?
C1 C2 C11 C10 76(3) . . . . ?
C3 C2 C11 C10 -167(3) . . . . ?
C7 C2 C11 C10 -70(3) . . . . ?
C7' C2 C11 C10 -35(4) . . . . ?
C11' C2 C11 C10 50(4) . . . . ?
C1 C2 C11 C19 -37(2) . . . . ?
C3 C2 C11 C19 80.5(17) . . . . ?
C7 C2 C11 C19 176.8(18) . . . . ?
C7' C2 C11 C19 -148(2) . . . . ?
C11' C2 C11 C19 -63(4) . . . . ?
O5 C9 C10' C11' -149(4) . . . . ?
C8' C9 C10' C11' 55(7) . . . . ?
C10 C9 C10' C11' -44(12) . . . . ?
C8 C9 C10' C11' 35(6) . . . . ?
C9 C10' C11' C19 -175(3) . . . . ?
C9 C10' C11' C2 -53(6) . . . . ?
C1 C2 C11' C10' 149(4) . . . . ?
C3 C2 C11' C10' -96(4) . . . . ?
C11 C2 C11' C10' -54(4) . . . . ?
C7 C2 C11' C10' 21(4) . . . . ?
C7' C2 C11' C10' 57(4) . . . . ?
C1 C2 C11' C19 -94(2) . . . . ?
C3 C2 C11' C19 21(3) . . . . ?
C11 C2 C11' C19 64(3) . . . . ?
C7 C2 C11' C19 138(2) . . . . ?
C7' C2 C11' C19 174(2) . . . . ?
C8 C7 C12 C17 -134(3) . . . . ?
C2 C7 C12 C17 111.1(18) . . . . ?
C8 C7 C12 C13 56(4) . . . . ?
C2 C7 C12 C13 -59(2) . . . . ?
C8 C7 C12 C7' 51(4) . . . . ?
C2 C7 C12 C7' -64(3) . . . . ?
C8' C7' C12 C17 -66(6) . . . . ?
C2 C7' C12 C17 54(4) . . . . ?
C8' C7' C12 C13 125(5) . . . . ?
C2 C7' C12 C13 -114(2) . . . . ?
C8' C7' C12 C7 -58(6) . . . . ?
C2 C7' C12 C7 62(3) . . . . ?
C17 C12 C13 C14 3.9(12) . . . . ?
C7 C12 C13 C14 173.1(14) . . . . ?
C7' C12 C13 C14 175.8(14) . . . . ?
C18 O6 C14 C15 6.9(9) . . . . ?
C18 O6 C14 C13 -170.8(8) . . . . ?
C12 C13 C14 O6 175.3(8) . . . . ?
C12 C13 C14 C15 -2.1(13) . . . . ?
C18 O7 C15 C14 -8.6(10) . . . . ?
C18 O7 C15 C16 169.9(8) . . . . ?
O6 C14 C15 O7 1.1(11) . . . . ?
C13 C14 C15 O7 179.0(7) . . . . ?
O6 C14 C15 C16 -177.4(8) . . . . ?
C13 C14 C15 C16 0.5(14) . . . . ?
O7 C15 C16 C17 -179.0(7) . . . . ?
C14 C15 C16 C17 -0.6(13) . . . . ?
C13 C12 C17 C16 -4.4(15) . . . . ?
C7 C12 C17 C16 -176.2(12) . . . . ?
C7' C12 C17 C16 -171(2) . . . . ?
C15 C16 C17 C12 2.7(13) . . . . ?
C15 O7 C18 O6 12.2(8) . . . . ?
C14 O6 C18 O7 -12.2(9) . . . . ?
C10' C11' C19 C24 -137(4) . . . . ?
C2 C11' C19 C24 103(2) . . . . ?
C10' C11' C19 C20 45(5) . . . . ?
C2 C11' C19 C20 -75(3) . . . . ?
C10' C11' C19 C11 57(4) . . . . ?
C2 C11' C19 C11 -63(3) . . . . ?
C10 C11 C19 C24 -67(3) . . . . ?
C2 C11 C19 C24 44(3) . . . . ?
C10 C11 C19 C20 125(3) . . . . ?
C2 C11 C19 C20 -124.1(16) . . . . ?
C10 C11 C19 C11' -47(3) . . . . ?
C2 C11 C19 C11' 64(3) . . . . ?
C24 C19 C20 C21 1.6(11) . . . . ?
C11' C19 C20 C21 180(2) . . . . ?
C11 C19 C20 C21 172.7(11) . . . . ?
C25 O8 C21 C20 -175.3(8) . . . . ?
C25 O8 C21 C22 4.0(9) . . . . ?
C19 C20 C21 O8 178.7(7) . . . . ?
C19 C20 C21 C22 -0.5(11) . . . . ?
C25 O9 C22 C21 -6.4(9) . . . . ?
C25 O9 C22 C23 173.9(8) . . . . ?
O8 C21 C22 O9 1.6(10) . . . . ?
C20 C21 C22 O9 -179.0(7) . . . . ?
O8 C21 C22 C23 -178.7(7) . . . . ?
C20 C21 C22 C23 0.7(13) . . . . ?
O9 C22 C23 C24 178.0(7) . . . . ?
C21 C22 C23 C24 -1.7(11) . . . . ?
C20 C19 C24 C23 -3.1(13) . . . . ?
C11' C19 C24 C23 178.3(14) . . . . ?
C11 C19 C24 C23 -170.6(15) . . . . ?
C22 C23 C24 C19 3.0(12) . . . . ?
C21 O8 C25 O9 -7.8(9) . . . . ?
C22 O9 C25 O8 8.7(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.052