# Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2010

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Fairlamb, Ian'
_publ_contact_author_email       ijsf1@york.ac.uk

_publ_section_title              
;
Atropisomerisation in sterically
hindered alpha,beta-disubstituted cyclopentenones derived
from an intermolecular cobalt(0)-mediated Pauson-Khand reaction
;
loop_
_publ_author_name
B.Moulton
J.Lynam
A.Duhme-Klair
W.Zheng
Z.Lin
I.Fairlamb

# Attachment '- ijf0629m.cif'

data_ijf0629m
_database_code_depnum_ccdc_archive 'CCDC 780325'
#TrackingRef '- ijf0629m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H10 Co2 O8'
_chemical_formula_sum            'C23 H10 Co2 O8'
_chemical_formula_weight         532.17

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'
Co Co 0.3494 0.9721 '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                   8.6456(6)
_cell_length_b                   8.9910(6)
_cell_length_c                   14.7003(10)
_cell_angle_alpha                80.2050(10)
_cell_angle_beta                 74.6770(10)
_cell_angle_gamma                73.2410(10)
_cell_volume                     1049.79(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4916
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      28.23

_exptl_crystal_description       Block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(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            10916
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         28.30
_reflns_number_total             5160
_reflns_number_gt                4519
_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, 1997)'
_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^)+(0.0348P)^2^+0.2831P] 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         5160
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0737
_refine_ls_wR_factor_gt          0.0709
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8525(2) 0.39353(19) 0.94998(12) 0.0169(3) Uani 1 1 d . . .
C2 C 0.84391(19) 0.53242(19) 0.88204(12) 0.0161(3) Uani 1 1 d . . .
H2 H 0.9244 0.5896 0.8733 0.019 Uiso 1 1 calc R . .
C3 C 0.72554(19) 0.58364(18) 0.83066(11) 0.0140(3) Uani 1 1 d . . .
C4 C 0.60075(19) 0.49598(19) 0.84471(12) 0.0152(3) Uani 1 1 d . . .
C5 C 0.4722(2) 0.5356(2) 0.79602(12) 0.0188(3) Uani 1 1 d . . .
H5 H 0.4639 0.6238 0.7500 0.023 Uiso 1 1 calc R . .
C6 C 0.3576(2) 0.4477(2) 0.81443(13) 0.0217(4) Uani 1 1 d . . .
H6 H 0.2722 0.4751 0.7805 0.026 Uiso 1 1 calc R . .
C7 C 0.3673(2) 0.3192(2) 0.88250(13) 0.0222(4) Uani 1 1 d . . .
H7 H 0.2876 0.2599 0.8955 0.027 Uiso 1 1 calc R . .
C8 C 0.4924(2) 0.2776(2) 0.93123(12) 0.0200(3) Uani 1 1 d . . .
H8 H 0.4993 0.1900 0.9778 0.024 Uiso 1 1 calc R . .
C9 C 0.60797(19) 0.36569(19) 0.91123(12) 0.0161(3) Uani 1 1 d . . .
C10 C 0.71916(19) 0.72548(19) 0.76423(11) 0.0148(3) Uani 1 1 d . . .
C11 C 0.61558(19) 0.85844(19) 0.73489(11) 0.0155(3) Uani 1 1 d . . .
C12 C 0.4439(2) 0.95244(19) 0.75296(12) 0.0162(3) Uani 1 1 d . . .
C13 C 0.3887(2) 1.0749(2) 0.68719(13) 0.0219(4) Uani 1 1 d . . .
H13 H 0.4637 1.0975 0.6297 0.026 Uiso 1 1 calc R . .
C14 C 0.2258(2) 1.1636(2) 0.70513(14) 0.0274(4) Uani 1 1 d . . .
H14 H 0.1891 1.2461 0.6599 0.033 Uiso 1 1 calc R . .
C15 C 0.1162(2) 1.1319(2) 0.78901(14) 0.0263(4) Uani 1 1 d . . .
H15 H 0.0044 1.1929 0.8011 0.032 Uiso 1 1 calc R . .
C16 C 0.1690(2) 1.0118(2) 0.85519(13) 0.0243(4) Uani 1 1 d . . .
H16 H 0.0938 0.9911 0.9129 0.029 Uiso 1 1 calc R . .
C17 C 0.3319(2) 0.9215(2) 0.83731(12) 0.0193(3) Uani 1 1 d . . .
H17 H 0.3673 0.8383 0.8826 0.023 Uiso 1 1 calc R . .
C18 C 0.7876(2) 0.92789(19) 0.86491(12) 0.0180(3) Uani 1 1 d . . .
C19 C 1.0490(2) 0.81554(19) 0.71700(12) 0.0179(3) Uani 1 1 d . . .
C20 C 0.8000(2) 1.1012(2) 0.68945(13) 0.0235(4) Uani 1 1 d . . .
C21 C 0.9700(2) 0.6162(2) 0.59610(13) 0.0257(4) Uani 1 1 d . . .
C22 C 0.7971(2) 0.9259(2) 0.53316(13) 0.0263(4) Uani 1 1 d . . .
C23 C 0.6396(2) 0.6915(3) 0.57783(14) 0.0295(4) Uani 1 1 d . . .
Co1 Co 0.82415(3) 0.89848(3) 0.741971(15) 0.01454(7) Uani 1 1 d . . .
Co2 Co 0.77451(3) 0.76532(3) 0.623944(15) 0.01648(7) Uani 1 1 d . . .
O1 O 0.73025(14) 0.31575(14) 0.96182(8) 0.0187(2) Uani 1 1 d . . .
O2 O 0.95552(15) 0.33859(14) 0.99589(9) 0.0229(3) Uani 1 1 d . . .
O3 O 0.76315(16) 0.94315(15) 0.94264(9) 0.0249(3) Uani 1 1 d . . .
O4 O 1.18698(15) 0.76056(15) 0.69844(9) 0.0244(3) Uani 1 1 d . . .
O5 O 0.7827(2) 1.22835(17) 0.65882(12) 0.0403(4) Uani 1 1 d . . .
O6 O 1.0913(2) 0.52384(19) 0.58101(12) 0.0428(4) Uani 1 1 d . . .
O7 O 0.8118(2) 1.02917(19) 0.47909(11) 0.0432(4) Uani 1 1 d . . .
O8 O 0.5535(2) 0.6515(2) 0.54654(12) 0.0481(4) Uani 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
C1 0.0169(7) 0.0159(8) 0.0179(8) -0.0016(6) -0.0041(6) -0.0042(6)
C2 0.0155(7) 0.0162(8) 0.0172(8) 0.0000(6) -0.0043(6) -0.0054(6)
C3 0.0145(7) 0.0131(7) 0.0141(7) -0.0021(6) -0.0017(6) -0.0039(6)
C4 0.0143(7) 0.0150(7) 0.0171(8) -0.0026(6) -0.0040(6) -0.0043(6)
C5 0.0197(8) 0.0169(8) 0.0213(8) 0.0013(6) -0.0092(7) -0.0047(6)
C6 0.0202(8) 0.0199(8) 0.0284(9) -0.0001(7) -0.0112(7) -0.0067(7)
C7 0.0193(8) 0.0201(8) 0.0297(10) -0.0004(7) -0.0062(7) -0.0097(7)
C8 0.0210(8) 0.0180(8) 0.0209(9) 0.0019(7) -0.0053(7) -0.0064(7)
C9 0.0143(7) 0.0176(8) 0.0162(8) -0.0020(6) -0.0042(6) -0.0030(6)
C10 0.0156(7) 0.0177(8) 0.0135(7) -0.0007(6) -0.0051(6) -0.0071(6)
C11 0.0166(7) 0.0182(8) 0.0130(7) 0.0000(6) -0.0036(6) -0.0073(6)
C12 0.0163(7) 0.0168(8) 0.0173(8) -0.0023(6) -0.0059(6) -0.0049(6)
C13 0.0213(8) 0.0223(9) 0.0212(9) 0.0012(7) -0.0072(7) -0.0042(7)
C14 0.0280(10) 0.0223(9) 0.0319(10) -0.0027(8) -0.0143(8) 0.0006(7)
C15 0.0163(8) 0.0295(10) 0.0362(11) -0.0173(8) -0.0097(7) 0.0009(7)
C16 0.0193(8) 0.0351(10) 0.0226(9) -0.0133(8) -0.0019(7) -0.0101(7)
C17 0.0196(8) 0.0243(9) 0.0166(8) -0.0036(7) -0.0053(6) -0.0078(7)
C18 0.0155(7) 0.0174(8) 0.0223(9) 0.0001(6) -0.0056(6) -0.0059(6)
C19 0.0217(8) 0.0190(8) 0.0153(8) 0.0017(6) -0.0063(6) -0.0085(7)
C20 0.0257(9) 0.0239(9) 0.0232(9) 0.0002(7) -0.0087(7) -0.0084(7)
C21 0.0294(10) 0.0278(10) 0.0201(9) -0.0070(7) -0.0072(7) -0.0034(8)
C22 0.0272(9) 0.0334(10) 0.0171(9) -0.0011(8) -0.0052(7) -0.0067(8)
C23 0.0284(10) 0.0408(11) 0.0196(9) -0.0066(8) -0.0014(7) -0.0109(8)
Co1 0.01434(11) 0.01522(12) 0.01483(12) 0.00094(8) -0.00449(8) -0.00534(8)
Co2 0.01692(12) 0.01906(12) 0.01330(12) -0.00115(9) -0.00393(8) -0.00419(9)
O1 0.0193(6) 0.0190(6) 0.0197(6) 0.0047(5) -0.0091(5) -0.0074(5)
O2 0.0227(6) 0.0220(6) 0.0256(7) 0.0031(5) -0.0131(5) -0.0045(5)
O3 0.0279(7) 0.0272(7) 0.0198(7) -0.0036(5) -0.0060(5) -0.0062(5)
O4 0.0187(6) 0.0271(7) 0.0257(7) 0.0008(5) -0.0066(5) -0.0039(5)
O5 0.0563(10) 0.0222(7) 0.0447(9) 0.0096(7) -0.0205(8) -0.0131(7)
O6 0.0381(9) 0.0394(9) 0.0440(9) -0.0165(7) -0.0140(7) 0.0120(7)
O7 0.0606(11) 0.0426(9) 0.0244(8) 0.0136(7) -0.0099(7) -0.0195(8)
O8 0.0407(9) 0.0831(13) 0.0351(9) -0.0212(9) -0.0076(7) -0.0303(9)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.201(2) . ?
C1 O1 1.3872(19) . ?
C1 C2 1.457(2) . ?
C2 C3 1.360(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.465(2) . ?
C3 C10 1.465(2) . ?
C4 C9 1.390(2) . ?
C4 C5 1.407(2) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(2) . ?
C8 H8 0.9500 . ?
C9 O1 1.3786(19) . ?
C10 C11 1.352(2) . ?
C10 Co1 1.9582(16) . ?
C10 Co2 1.9839(16) . ?
C11 C12 1.461(2) . ?
C11 Co2 1.9662(16) . ?
C11 Co1 1.9694(16) . ?
C12 C13 1.397(2) . ?
C12 C17 1.399(2) . ?
C13 C14 1.385(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 O3 1.130(2) . ?
C18 Co1 1.8024(18) . ?
C19 O4 1.129(2) . ?
C19 Co1 1.8304(17) . ?
C20 O5 1.137(2) . ?
C20 Co1 1.8302(19) . ?
C21 O6 1.130(2) . ?
C21 Co2 1.8264(19) . ?
C22 O7 1.129(2) . ?
C22 Co2 1.8090(19) . ?
C23 O8 1.134(2) . ?
C23 Co2 1.811(2) . ?
Co1 Co2 2.4545(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 116.74(15) . . ?
O2 C1 C2 126.73(15) . . ?
O1 C1 C2 116.52(14) . . ?
C3 C2 C1 122.81(14) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 C3 C4 118.54(14) . . ?
C2 C3 C10 121.22(14) . . ?
C4 C3 C10 120.23(14) . . ?
C9 C4 C5 117.47(14) . . ?
C9 C4 C3 118.15(14) . . ?
C5 C4 C3 124.38(15) . . ?
C6 C5 C4 120.80(16) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.18(16) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.20(16) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.07(16) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
O1 C9 C4 122.03(14) . . ?
O1 C9 C8 115.69(14) . . ?
C4 C9 C8 122.28(15) . . ?
C11 C10 C3 143.46(15) . . ?
C11 C10 Co1 70.31(10) . . ?
C3 C10 Co1 134.28(12) . . ?
C11 C10 Co2 69.28(10) . . ?
C3 C10 Co2 133.85(12) . . ?
Co1 C10 Co2 77.02(6) . . ?
C10 C11 C12 143.80(15) . . ?
C10 C11 Co2 70.69(10) . . ?
C12 C11 Co2 134.80(12) . . ?
C10 C11 Co1 69.42(9) . . ?
C12 C11 Co1 132.49(12) . . ?
Co2 C11 Co1 77.17(6) . . ?
C13 C12 C17 118.87(16) . . ?
C13 C12 C11 120.97(15) . . ?
C17 C12 C11 120.16(15) . . ?
C14 C13 C12 120.50(17) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.06(17) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.18(17) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.08(17) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.30(16) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
O3 C18 Co1 178.28(15) . . ?
O4 C19 Co1 176.71(16) . . ?
O5 C20 Co1 178.37(19) . . ?
O6 C21 Co2 178.37(17) . . ?
O7 C22 Co2 177.31(18) . . ?
O8 C23 Co2 176.9(2) . . ?
C18 Co1 C20 99.40(8) . . ?
C18 Co1 C19 99.51(7) . . ?
C20 Co1 C19 103.94(8) . . ?
C18 Co1 C10 96.26(7) . . ?
C20 Co1 C10 141.62(7) . . ?
C19 Co1 C10 107.70(7) . . ?
C18 Co1 C11 102.79(7) . . ?
C20 Co1 C11 101.81(7) . . ?
C19 Co1 C11 142.40(7) . . ?
C10 Co1 C11 40.27(7) . . ?
C18 Co1 Co2 147.87(5) . . ?
C20 Co1 Co2 104.24(6) . . ?
C19 Co1 Co2 95.60(5) . . ?
C10 Co1 Co2 51.96(5) . . ?
C11 Co1 Co2 51.36(5) . . ?
C22 Co2 C23 97.79(9) . . ?
C22 Co2 C21 104.79(9) . . ?
C23 Co2 C21 101.39(9) . . ?
C22 Co2 C11 106.03(8) . . ?
C23 Co2 C11 99.94(8) . . ?
C21 Co2 C11 139.39(7) . . ?
C22 Co2 C10 139.26(8) . . ?
C23 Co2 C10 108.36(8) . . ?
C21 Co2 C10 100.09(8) . . ?
C11 Co2 C10 40.03(7) . . ?
C22 Co2 Co1 92.13(6) . . ?
C23 Co2 Co1 151.40(6) . . ?
C21 Co2 Co1 101.87(6) . . ?
C11 Co2 Co1 51.47(5) . . ?
C10 Co2 Co1 51.02(5) . . ?
C9 O1 C1 121.92(13) . . ?

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
O2 C1 C2 C3 177.76(17) . . . . ?
O1 C1 C2 C3 -1.3(2) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C3 C10 178.89(15) . . . . ?
C2 C3 C4 C9 1.0(2) . . . . ?
C10 C3 C4 C9 -177.48(15) . . . . ?
C2 C3 C4 C5 -179.71(16) . . . . ?
C10 C3 C4 C5 1.8(2) . . . . ?
C9 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C6 -179.10(16) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C5 C4 C9 O1 179.12(15) . . . . ?
C3 C4 C9 O1 -1.5(2) . . . . ?
C5 C4 C9 C8 -1.0(2) . . . . ?
C3 C4 C9 C8 178.29(15) . . . . ?
C7 C8 C9 O1 -179.17(16) . . . . ?
C7 C8 C9 C4 1.0(3) . . . . ?
C2 C3 C10 C11 -135.1(2) . . . . ?
C4 C3 C10 C11 43.3(3) . . . . ?
C2 C3 C10 Co1 -13.4(2) . . . . ?
C4 C3 C10 Co1 164.99(13) . . . . ?
C2 C3 C10 Co2 106.66(18) . . . . ?
C4 C3 C10 Co2 -74.9(2) . . . . ?
C3 C10 C11 C12 4.6(4) . . . . ?
Co1 C10 C11 C12 -135.1(3) . . . . ?
Co2 C10 C11 C12 141.8(3) . . . . ?
C3 C10 C11 Co2 -137.2(2) . . . . ?
Co1 C10 C11 Co2 83.12(5) . . . . ?
C3 C10 C11 Co1 139.7(3) . . . . ?
Co2 C10 C11 Co1 -83.12(5) . . . . ?
C10 C11 C12 C13 -167.0(2) . . . . ?
Co2 C11 C12 C13 -42.4(2) . . . . ?
Co1 C11 C12 C13 76.6(2) . . . . ?
C10 C11 C12 C17 13.5(3) . . . . ?
Co2 C11 C12 C17 138.06(15) . . . . ?
Co1 C11 C12 C17 -102.92(18) . . . . ?
C17 C12 C13 C14 -0.3(3) . . . . ?
C11 C12 C13 C14 -179.84(16) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 C17 C12 0.8(3) . . . . ?
C13 C12 C17 C16 -0.3(2) . . . . ?
C11 C12 C17 C16 179.25(16) . . . . ?
C11 C10 Co1 C18 102.42(11) . . . . ?
C3 C10 Co1 C18 -45.03(17) . . . . ?
Co2 C10 Co1 C18 174.78(6) . . . . ?
C11 C10 Co1 C20 -11.36(17) . . . . ?
C3 C10 Co1 C20 -158.81(15) . . . . ?
Co2 C10 Co1 C20 61.00(13) . . . . ?
C11 C10 Co1 C19 -155.48(10) . . . . ?
C3 C10 Co1 C19 57.07(17) . . . . ?
Co2 C10 Co1 C19 -83.13(7) . . . . ?
C3 C10 Co1 C11 -147.5(2) . . . . ?
Co2 C10 Co1 C11 72.35(9) . . . . ?
C11 C10 Co1 Co2 -72.35(9) . . . . ?
C3 C10 Co1 Co2 140.20(18) . . . . ?
C10 C11 Co1 C18 -84.55(11) . . . . ?
C12 C11 Co1 C18 61.04(17) . . . . ?
Co2 C11 Co1 C18 -158.48(6) . . . . ?
C10 C11 Co1 C20 172.83(11) . . . . ?
C12 C11 Co1 C20 -41.59(17) . . . . ?
Co2 C11 Co1 C20 98.89(7) . . . . ?
C10 C11 Co1 C19 40.39(16) . . . . ?
C12 C11 Co1 C19 -174.03(14) . . . . ?
Co2 C11 Co1 C19 -33.55(13) . . . . ?
C12 C11 Co1 C10 145.6(2) . . . . ?
Co2 C11 Co1 C10 -73.93(9) . . . . ?
C10 C11 Co1 Co2 73.93(9) . . . . ?
C12 C11 Co1 Co2 -140.48(18) . . . . ?
C10 C11 Co2 C22 -152.08(10) . . . . ?
C12 C11 Co2 C22 58.94(18) . . . . ?
Co1 C11 Co2 C22 -79.67(8) . . . . ?
C10 C11 Co2 C23 106.77(11) . . . . ?
C12 C11 Co2 C23 -42.22(18) . . . . ?
Co1 C11 Co2 C23 179.18(7) . . . . ?
C10 C11 Co2 C21 -14.06(16) . . . . ?
C12 C11 Co2 C21 -163.05(16) . . . . ?
Co1 C11 Co2 C21 58.35(13) . . . . ?
C12 C11 Co2 C10 -149.0(2) . . . . ?
Co1 C11 Co2 C10 72.41(9) . . . . ?
C10 C11 Co2 Co1 -72.41(9) . . . . ?
C12 C11 Co2 Co1 138.60(19) . . . . ?
C11 C10 Co2 C22 43.60(15) . . . . ?
C3 C10 Co2 C22 -170.52(15) . . . . ?
Co1 C10 Co2 C22 -29.99(13) . . . . ?
C11 C10 Co2 C23 -83.55(11) . . . . ?
C3 C10 Co2 C23 62.33(17) . . . . ?
Co1 C10 Co2 C23 -157.14(8) . . . . ?
C11 C10 Co2 C21 170.76(11) . . . . ?
C3 C10 Co2 C21 -43.37(17) . . . . ?
Co1 C10 Co2 C21 97.17(7) . . . . ?
C3 C10 Co2 C11 145.9(2) . . . . ?
Co1 C10 Co2 C11 -73.59(9) . . . . ?
C11 C10 Co2 Co1 73.59(9) . . . . ?
C3 C10 Co2 Co1 -140.53(18) . . . . ?
C18 Co1 Co2 C22 151.15(12) . . . . ?
C20 Co1 Co2 C22 15.02(9) . . . . ?
C19 Co1 Co2 C22 -90.92(8) . . . . ?
C10 Co1 Co2 C22 160.95(9) . . . . ?
C11 Co1 Co2 C22 108.88(9) . . . . ?
C18 Co1 Co2 C23 40.57(18) . . . . ?
C20 Co1 Co2 C23 -95.55(15) . . . . ?
C19 Co1 Co2 C23 158.51(15) . . . . ?
C10 Co1 Co2 C23 50.38(15) . . . . ?
C11 Co1 Co2 C23 -1.69(15) . . . . ?
C18 Co1 Co2 C21 -103.25(12) . . . . ?
C20 Co1 Co2 C21 120.62(9) . . . . ?
C19 Co1 Co2 C21 14.68(8) . . . . ?
C10 Co1 Co2 C21 -93.45(9) . . . . ?
C11 Co1 Co2 C21 -145.52(9) . . . . ?
C18 Co1 Co2 C11 42.26(12) . . . . ?
C20 Co1 Co2 C11 -93.86(8) . . . . ?
C19 Co1 Co2 C11 160.20(8) . . . . ?
C10 Co1 Co2 C11 52.06(8) . . . . ?
C18 Co1 Co2 C10 -9.80(12) . . . . ?
C20 Co1 Co2 C10 -145.93(8) . . . . ?
C19 Co1 Co2 C10 108.13(8) . . . . ?
C11 Co1 Co2 C10 -52.06(8) . . . . ?
C4 C9 O1 C1 0.6(2) . . . . ?
C8 C9 O1 C1 -179.23(15) . . . . ?
O2 C1 O1 C9 -178.38(15) . . . . ?
C2 C1 O1 C9 0.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.074

# Attachment '- ijf0810a.cif'

data_ijf0810a
_database_code_depnum_ccdc_archive 'CCDC 780326'
#TrackingRef '- ijf0810a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H20 O3'
_chemical_formula_sum            'C25 H20 O3'
_chemical_formula_weight         368.41

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           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                   13.6217(8)
_cell_length_b                   12.1491(7)
_cell_length_c                   12.2859(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.6790(10)
_cell_angle_gamma                90.00
_cell_volume                     1889.40(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5296
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      24.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'

_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            19047
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         28.36
_reflns_number_total             4702
_reflns_number_gt                3372
_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, 1997)'
_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^)+(0.0541P)^2^+0.3011P] 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         4702
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C1 C 0.32658(13) 0.51769(13) 0.36496(17) 0.0660(5) Uani 1 1 d . . .
C2 C 0.23506(12) 0.58843(11) 0.31951(15) 0.0551(4) Uani 1 1 d . . .
H2 H 0.1722 0.5655 0.3256 0.066 Uiso 1 1 calc R . .
C3 C 0.23704(10) 0.68597(10) 0.26878(12) 0.0422(3) Uani 1 1 d . . .
C4 C 0.33415(10) 0.72038(10) 0.25494(12) 0.0438(3) Uani 1 1 d . . .
C5 C 0.34370(12) 0.81341(11) 0.19315(13) 0.0514(3) Uani 1 1 d . . .
H5 H 0.2853 0.8584 0.1577 0.062 Uiso 1 1 calc R . .
C6 C 0.43854(14) 0.83930(14) 0.18408(16) 0.0643(4) Uani 1 1 d . . .
H6 H 0.4438 0.9005 0.1410 0.077 Uiso 1 1 calc R . .
C7 C 0.52630(13) 0.77416(15) 0.23914(19) 0.0743(5) Uani 1 1 d . . .
H7 H 0.5908 0.7933 0.2347 0.089 Uiso 1 1 calc R . .
C8 C 0.51955(13) 0.68216(15) 0.29995(18) 0.0709(5) Uani 1 1 d . . .
H8 H 0.5788 0.6388 0.3370 0.085 Uiso 1 1 calc R . .
C9 C 0.42284(11) 0.65462(12) 0.30550(14) 0.0541(4) Uani 1 1 d . . .
C10 C 0.14109(10) 0.75548(10) 0.22821(11) 0.0387(3) Uani 1 1 d . . .
C11 C 0.13359(10) 0.86132(10) 0.25760(11) 0.0388(3) Uani 1 1 d . . .
C12 C 0.02356(10) 0.89894(10) 0.19397(11) 0.0410(3) Uani 1 1 d . . .
C13 C -0.04069(10) 0.80442(10) 0.12404(11) 0.0405(3) Uani 1 1 d . . .
H13 H -0.0996 0.7862 0.1484 0.049 Uiso 1 1 calc R . .
C14 C 0.03800(10) 0.70794(10) 0.14650(11) 0.0396(3) Uani 1 1 d . . .
H14 H 0.0160 0.6449 0.1817 0.048 Uiso 1 1 calc R . .
C15 C 0.03418(12) 0.68097(11) 0.02230(13) 0.0499(3) Uani 1 1 d . . .
H15 H 0.0948 0.6390 0.0198 0.060 Uiso 1 1 calc R . .
C16 C -0.07375(14) 0.62854(12) -0.04437(14) 0.0613(4) Uani 1 1 d . . .
H16A H -0.0908 0.5735 0.0031 0.074 Uiso 1 1 calc R . .
H16B H -0.0755 0.5947 -0.1166 0.074 Uiso 1 1 calc R . .
C17 C -0.15073(13) 0.72743(13) -0.06953(14) 0.0618(4) Uani 1 1 d . . .
H17A H -0.1847 0.7405 -0.1530 0.074 Uiso 1 1 calc R . .
H17B H -0.2045 0.7155 -0.0365 0.074 Uiso 1 1 calc R . .
C18 C -0.07846(12) 0.82287(11) -0.00908(12) 0.0500(3) Uani 1 1 d . . .
H18 H -0.1078 0.8961 -0.0354 0.060 Uiso 1 1 calc R . .
C19 C 0.02083(13) 0.79505(12) -0.03348(13) 0.0533(4) Uani 1 1 d . . .
H19A H 0.0082 0.7924 -0.1165 0.064 Uiso 1 1 calc R . .
H19B H 0.0794 0.8438 0.0066 0.064 Uiso 1 1 calc R . .
C20 C 0.21492(10) 0.93339(11) 0.33828(11) 0.0419(3) Uani 1 1 d . . .
C21 C 0.22086(12) 1.04359(12) 0.31110(13) 0.0523(3) Uani 1 1 d . . .
H21 H 0.1714 1.0723 0.2426 0.063 Uiso 1 1 calc R . .
C22 C 0.29895(14) 1.11104(14) 0.38405(16) 0.0646(4) Uani 1 1 d . . .
H22 H 0.3022 1.1845 0.3643 0.078 Uiso 1 1 calc R . .
C23 C 0.37173(14) 1.06966(16) 0.48566(16) 0.0716(5) Uani 1 1 d . . .
H23 H 0.4251 1.1146 0.5345 0.086 Uiso 1 1 calc R . .
C24 C 0.36547(14) 0.96169(17) 0.51489(15) 0.0729(5) Uani 1 1 d . . .
H24 H 0.4143 0.9340 0.5844 0.087 Uiso 1 1 calc R . .
C25 C 0.28785(12) 0.89376(13) 0.44273(13) 0.0556(4) Uani 1 1 d . . .
H25 H 0.2843 0.8209 0.4641 0.067 Uiso 1 1 calc R . .
O1 O 0.41909(8) 0.55777(9) 0.36132(11) 0.0677(3) Uani 1 1 d . . .
O2 O 0.32878(11) 0.42820(10) 0.40664(16) 0.1010(5) Uani 1 1 d . . .
O3 O -0.00938(8) 0.99126(8) 0.19612(10) 0.0595(3) Uani 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
C1 0.0567(10) 0.0455(8) 0.0919(13) 0.0158(8) 0.0231(9) 0.0120(7)
C2 0.0452(8) 0.0413(7) 0.0795(10) 0.0141(7) 0.0239(8) 0.0062(6)
C3 0.0404(7) 0.0345(6) 0.0525(7) 0.0027(5) 0.0182(6) 0.0037(5)
C4 0.0410(7) 0.0383(7) 0.0544(8) -0.0062(6) 0.0203(6) -0.0003(5)
C5 0.0524(8) 0.0464(8) 0.0619(9) -0.0034(6) 0.0286(7) -0.0038(6)
C6 0.0663(11) 0.0581(9) 0.0810(11) -0.0108(8) 0.0418(9) -0.0182(8)
C7 0.0503(10) 0.0739(12) 0.1093(15) -0.0261(11) 0.0420(10) -0.0171(8)
C8 0.0402(9) 0.0669(11) 0.1040(14) -0.0172(10) 0.0245(9) 0.0000(7)
C9 0.0441(8) 0.0453(8) 0.0719(10) -0.0091(7) 0.0203(7) 0.0015(6)
C10 0.0405(7) 0.0344(6) 0.0452(7) 0.0096(5) 0.0206(6) 0.0036(5)
C11 0.0418(7) 0.0361(6) 0.0410(7) 0.0063(5) 0.0183(5) 0.0045(5)
C12 0.0445(7) 0.0407(7) 0.0417(7) 0.0029(5) 0.0204(6) 0.0073(5)
C13 0.0386(7) 0.0412(7) 0.0437(7) 0.0051(5) 0.0178(6) 0.0038(5)
C14 0.0424(7) 0.0313(6) 0.0485(7) 0.0075(5) 0.0207(6) 0.0009(5)
C15 0.0608(9) 0.0401(7) 0.0556(8) -0.0027(6) 0.0293(7) 0.0026(6)
C16 0.0776(11) 0.0460(8) 0.0567(9) -0.0072(7) 0.0204(8) -0.0084(8)
C17 0.0636(10) 0.0604(9) 0.0514(9) 0.0020(7) 0.0096(7) -0.0044(8)
C18 0.0609(9) 0.0408(7) 0.0446(7) 0.0065(6) 0.0153(7) 0.0046(6)
C19 0.0721(10) 0.0495(8) 0.0449(8) 0.0017(6) 0.0292(7) -0.0066(7)
C20 0.0430(7) 0.0434(7) 0.0418(7) 0.0009(5) 0.0185(6) 0.0037(5)
C21 0.0578(9) 0.0456(8) 0.0495(8) 0.0018(6) 0.0151(7) -0.0020(6)
C22 0.0714(11) 0.0534(9) 0.0708(11) -0.0097(8) 0.0283(9) -0.0127(8)
C23 0.0609(10) 0.0822(12) 0.0654(11) -0.0221(9) 0.0161(9) -0.0147(9)
C24 0.0607(10) 0.0948(14) 0.0488(9) -0.0014(9) 0.0035(8) 0.0032(10)
C25 0.0562(9) 0.0586(9) 0.0485(8) 0.0075(7) 0.0151(7) 0.0070(7)
O1 0.0468(6) 0.0513(6) 0.0984(9) 0.0096(6) 0.0191(6) 0.0142(5)
O2 0.0836(10) 0.0572(8) 0.1566(14) 0.0500(8) 0.0379(9) 0.0243(7)
O3 0.0542(6) 0.0449(6) 0.0755(7) -0.0076(5) 0.0195(5) 0.0156(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
C1 O2 1.1974(18) . ?
C1 O1 1.367(2) . ?
C1 C2 1.446(2) . ?
C2 C3 1.3438(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.4559(18) . ?
C3 C10 1.4795(17) . ?
C4 C9 1.3890(19) . ?
C4 C5 1.3942(19) . ?
C5 C6 1.374(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(2) . ?
C8 H8 0.9300 . ?
C9 O1 1.3723(19) . ?
C10 C11 1.3497(17) . ?
C10 C14 1.5072(18) . ?
C11 C20 1.4715(18) . ?
C11 C12 1.4835(18) . ?
C12 O3 1.2120(15) . ?
C12 C13 1.5057(18) . ?
C13 C18 1.5389(18) . ?
C13 C14 1.5429(17) . ?
C13 H13 0.9800 . ?
C14 C15 1.5426(18) . ?
C14 H14 0.9800 . ?
C15 C19 1.5270(19) . ?
C15 C16 1.532(2) . ?
C15 H15 0.9800 . ?
C16 C17 1.549(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.525(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.527(2) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C25 1.3869(19) . ?
C20 C21 1.3894(19) . ?
C21 C22 1.379(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.376(2) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 117.37(14) . . ?
O2 C1 C2 125.92(16) . . ?
O1 C1 C2 116.70(13) . . ?
C3 C2 C1 122.76(14) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 C3 C4 118.83(12) . . ?
C2 C3 C10 119.53(12) . . ?
C4 C3 C10 121.63(11) . . ?
C9 C4 C5 117.98(13) . . ?
C9 C4 C3 117.40(12) . . ?
C5 C4 C3 124.61(12) . . ?
C6 C5 C4 120.63(15) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.86(16) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.97(15) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 118.81(16) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
O1 C9 C8 116.32(14) . . ?
O1 C9 C4 122.00(13) . . ?
C8 C9 C4 121.67(15) . . ?
C11 C10 C3 126.76(12) . . ?
C11 C10 C14 113.54(11) . . ?
C3 C10 C14 119.70(11) . . ?
C10 C11 C20 129.39(12) . . ?
C10 C11 C12 108.31(11) . . ?
C20 C11 C12 122.30(11) . . ?
O3 C12 C11 125.72(13) . . ?
O3 C12 C13 125.19(12) . . ?
C11 C12 C13 109.08(10) . . ?
C12 C13 C18 113.02(10) . . ?
C12 C13 C14 104.97(10) . . ?
C18 C13 C14 103.77(10) . . ?
C12 C13 H13 111.5 . . ?
C18 C13 H13 111.5 . . ?
C14 C13 H13 111.5 . . ?
C10 C14 C15 115.02(11) . . ?
C10 C14 C13 104.05(10) . . ?
C15 C14 C13 102.54(10) . . ?
C10 C14 H14 111.5 . . ?
C15 C14 H14 111.5 . . ?
C13 C14 H14 111.5 . . ?
C19 C15 C16 101.87(12) . . ?
C19 C15 C14 101.89(10) . . ?
C16 C15 C14 106.98(12) . . ?
C19 C15 H15 114.8 . . ?
C16 C15 H15 114.8 . . ?
C14 C15 H15 114.8 . . ?
C15 C16 C17 103.26(12) . . ?
C15 C16 H16A 111.1 . . ?
C17 C16 H16A 111.1 . . ?
C15 C16 H16B 111.1 . . ?
C17 C16 H16B 111.1 . . ?
H16A C16 H16B 109.1 . . ?
C18 C17 C16 103.00(13) . . ?
C18 C17 H17A 111.2 . . ?
C16 C17 H17A 111.2 . . ?
C18 C17 H17B 111.2 . . ?
C16 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
C17 C18 C19 101.26(12) . . ?
C17 C18 C13 108.01(11) . . ?
C19 C18 C13 101.76(11) . . ?
C17 C18 H18 114.7 . . ?
C19 C18 H18 114.7 . . ?
C13 C18 H18 114.7 . . ?
C15 C19 C18 94.59(11) . . ?
C15 C19 H19A 112.8 . . ?
C18 C19 H19A 112.8 . . ?
C15 C19 H19B 112.8 . . ?
C18 C19 H19B 112.8 . . ?
H19A C19 H19B 110.3 . . ?
C25 C20 C21 118.13(13) . . ?
C25 C20 C11 121.36(12) . . ?
C21 C20 C11 120.51(12) . . ?
C22 C21 C20 121.05(14) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 119.90(16) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 119.69(16) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 120.84(16) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C24 C25 C20 120.35(15) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
C1 O1 C9 121.78(11) . . ?

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
O2 C1 C2 C3 -176.75(19) . . . . ?
O1 C1 C2 C3 4.3(3) . . . . ?
C1 C2 C3 C4 2.3(2) . . . . ?
C1 C2 C3 C10 -177.83(15) . . . . ?
C2 C3 C4 C9 -6.1(2) . . . . ?
C10 C3 C4 C9 174.09(13) . . . . ?
C2 C3 C4 C5 172.88(14) . . . . ?
C10 C3 C4 C5 -7.0(2) . . . . ?
C9 C4 C5 C6 -0.7(2) . . . . ?
C3 C4 C5 C6 -179.63(14) . . . . ?
C4 C5 C6 C7 -1.6(2) . . . . ?
C5 C6 C7 C8 1.9(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 O1 176.00(16) . . . . ?
C7 C8 C9 C4 -2.6(3) . . . . ?
C5 C4 C9 O1 -175.67(13) . . . . ?
C3 C4 C9 O1 3.3(2) . . . . ?
C5 C4 C9 C8 2.9(2) . . . . ?
C3 C4 C9 C8 -178.14(14) . . . . ?
C2 C3 C10 C11 125.48(15) . . . . ?
C4 C3 C10 C11 -54.68(19) . . . . ?
C2 C3 C10 C14 -53.77(18) . . . . ?
C4 C3 C10 C14 126.08(13) . . . . ?
C3 C10 C11 C20 -2.2(2) . . . . ?
C14 C10 C11 C20 177.11(11) . . . . ?
C3 C10 C11 C12 178.40(11) . . . . ?
C14 C10 C11 C12 -2.32(14) . . . . ?
C10 C11 C12 O3 -176.53(13) . . . . ?
C20 C11 C12 O3 4.0(2) . . . . ?
C10 C11 C12 C13 2.40(14) . . . . ?
C20 C11 C12 C13 -177.07(11) . . . . ?
O3 C12 C13 C18 64.98(17) . . . . ?
C11 C12 C13 C18 -113.95(12) . . . . ?
O3 C12 C13 C14 177.40(12) . . . . ?
C11 C12 C13 C14 -1.53(13) . . . . ?
C11 C10 C14 C15 112.65(12) . . . . ?
C3 C10 C14 C15 -68.01(14) . . . . ?
C11 C10 C14 C13 1.31(14) . . . . ?
C3 C10 C14 C13 -179.35(10) . . . . ?
C12 C13 C14 C10 0.23(12) . . . . ?
C18 C13 C14 C10 119.06(11) . . . . ?
C12 C13 C14 C15 -119.92(11) . . . . ?
C18 C13 C14 C15 -1.08(13) . . . . ?
C10 C14 C15 C19 -76.38(13) . . . . ?
C13 C14 C15 C19 35.84(13) . . . . ?
C10 C14 C15 C16 177.11(11) . . . . ?
C13 C14 C15 C16 -70.66(12) . . . . ?
C19 C15 C16 C17 -32.83(15) . . . . ?
C14 C15 C16 C17 73.69(14) . . . . ?
C15 C16 C17 C18 -2.74(16) . . . . ?
C16 C17 C18 C19 37.35(14) . . . . ?
C16 C17 C18 C13 -69.11(15) . . . . ?
C12 C13 C18 C17 -174.71(11) . . . . ?
C14 C13 C18 C17 72.14(13) . . . . ?
C12 C13 C18 C19 79.18(13) . . . . ?
C14 C13 C18 C19 -33.97(12) . . . . ?
C16 C15 C19 C18 54.69(13) . . . . ?
C14 C15 C19 C18 -55.75(12) . . . . ?
C17 C18 C19 C15 -56.56(12) . . . . ?
C13 C18 C19 C15 54.76(12) . . . . ?
C10 C11 C20 C25 -39.0(2) . . . . ?
C12 C11 C20 C25 140.30(13) . . . . ?
C10 C11 C20 C21 140.63(14) . . . . ?
C12 C11 C20 C21 -40.03(18) . . . . ?
C25 C20 C21 C22 1.9(2) . . . . ?
C11 C20 C21 C22 -177.76(13) . . . . ?
C20 C21 C22 C23 -0.5(2) . . . . ?
C21 C22 C23 C24 -0.9(3) . . . . ?
C22 C23 C24 C25 0.9(3) . . . . ?
C23 C24 C25 C20 0.6(3) . . . . ?
C21 C20 C25 C24 -1.9(2) . . . . ?
C11 C20 C25 C24 177.74(14) . . . . ?
O2 C1 O1 C9 173.74(17) . . . . ?
C2 C1 O1 C9 -7.2(2) . . . . ?
C8 C9 O1 C1 -175.11(16) . . . . ?
C4 C9 O1 C1 3.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.032