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# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_21

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H30 O3'
_chemical_formula_sum            'C34 H30 O3'
_chemical_formula_weight         486.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.9566(15)
_cell_length_b                   10.2959(16)
_cell_length_c                   13.2929(19)
_cell_angle_alpha                74.756(4)
_cell_angle_beta                 76.427(4)
_cell_angle_gamma                79.167(4)
_cell_volume                     1266.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER AXS SMART APEX CCD with Mo source'
_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            11707
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.1324
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         28.47
_reflns_number_total             6347
_reflns_number_gt                3239
_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    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0650P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6347
_refine_ls_number_parameters     430
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001

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
H1 H 0.625(3) 0.533(2) 0.4518(19) 0.020(7) Uiso 1 1 d . . .
H2 H 0.584(2) 0.737(2) 0.5265(18) 0.017(6) Uiso 1 1 d . . .
H3 H 0.889(3) 0.357(2) 0.4476(18) 0.015(6) Uiso 1 1 d . . .
H4 H 0.750(2) 1.010(2) 0.1556(18) 0.020(6) Uiso 1 1 d . . .
H5 H 0.545(3) 0.838(3) 0.1585(18) 0.024(7) Uiso 1 1 d . . .
H6 H 0.861(2) 1.089(2) -0.0219(18) 0.016(6) Uiso 1 1 d . . .
H7 H 0.740(3) 0.306(2) 0.5039(18) 0.021(7) Uiso 1 1 d . . .
H8 H 0.494(3) 0.507(3) 0.337(2) 0.031(8) Uiso 1 1 d . . .
H9 H 0.894(3) 0.603(2) 0.3420(19) 0.028(7) Uiso 1 1 d . . .
H10 H 0.784(3) 0.285(3) 0.842(2) 0.026(7) Uiso 1 1 d . . .
H11 H 0.827(3) 0.501(3) 0.836(2) 0.035(8) Uiso 1 1 d . . .
H12 H 0.849(3) 0.668(3) 0.6794(19) 0.026(7) Uiso 1 1 d . . .
H14 H 0.724(3) 0.715(3) 0.0576(19) 0.025(7) Uiso 1 1 d . . .
H15 H 0.520(3) 0.999(3) 0.135(2) 0.028(7) Uiso 1 1 d . . .
H18 H 0.882(3) 0.760(2) 0.1977(18) 0.018(6) Uiso 1 1 d . . .
H17 H 0.956(3) 1.060(2) -0.1982(19) 0.025(7) Uiso 1 1 d . . .
H19 H 0.372(3) 0.862(2) 0.590(2) 0.028(7) Uiso 1 1 d . . .
H20 H 0.339(3) 1.045(3) 0.285(2) 0.033(8) Uiso 1 1 d . . .
H23 H 0.912(3) 0.411(3) 0.258(2) 0.033(8) Uiso 1 1 d . . .
H24 H 0.768(3) 0.230(3) 0.683(2) 0.034(8) Uiso 1 1 d . . .
H25 H 0.252(3) 1.022(3) 0.465(2) 0.037(8) Uiso 1 1 d . . .
H27 H 0.885(3) 0.340(3) 0.105(2) 0.050(9) Uiso 1 1 d . . .
H28 H 0.466(3) 0.437(3) 0.194(2) 0.040(8) Uiso 1 1 d . . .
H30 H 0.813(3) 0.699(3) -0.121(2) 0.034(8) Uiso 1 1 d . . .
O1 O 0.87820(17) 0.76102(16) 0.48131(13) 0.0219(4) Uani 1 1 d . . .
O2' O 0.93588(18) 0.85154(17) -0.27426(13) 0.0266(4) Uani 1 1 d . . .
O2 O 0.6654(2) 0.3382(2) 0.05004(14) 0.0342(5) Uani 1 1 d . . .
C1 C 0.8371(2) 0.6551(2) 0.48644(19) 0.0188(5) Uani 1 1 d . . .
C9 C 0.8237(2) 0.5457(2) 0.58721(18) 0.0170(5) Uani 1 1 d . . .
C8 C 0.8343(3) 0.5770(3) 0.68124(19) 0.0204(5) Uani 1 1 d . . .
C7 C 0.8221(3) 0.4774(3) 0.7750(2) 0.0242(6) Uani 1 1 d . . .
C6 C 0.7979(3) 0.3492(2) 0.7755(2) 0.0235(6) Uani 1 1 d . . .
C5 C 0.7881(3) 0.3180(3) 0.6822(2) 0.0224(6) Uani 1 1 d . . .
C10 C 0.8016(2) 0.4162(2) 0.58672(19) 0.0188(5) Uani 1 1 d . . .
C4 C 0.7915(3) 0.3829(2) 0.4860(2) 0.0208(5) Uani 1 1 d . . .
C3 C 0.7198(3) 0.5044(2) 0.41345(19) 0.0189(5) Uani 1 1 d . . .
C2 C 0.8009(3) 0.6277(2) 0.38878(19) 0.0180(5) Uani 1 1 d . . .
C1' C 0.7298(2) 0.7539(2) 0.32268(18) 0.0190(5) Uani 1 1 d . . .
C9' C 0.5913(2) 0.8198(2) 0.36753(19) 0.0189(5) Uani 1 1 d . . .
C8' C 0.5354(3) 0.8016(2) 0.47568(19) 0.0204(5) Uani 1 1 d . . .
C7' C 0.4100(3) 0.8744(2) 0.5132(2) 0.0240(6) Uani 1 1 d . . .
C6' C 0.3369(3) 0.9680(3) 0.4422(2) 0.0255(6) Uani 1 1 d . . .
C5' C 0.3887(3) 0.9847(3) 0.3340(2) 0.0255(6) Uani 1 1 d . . .
C10' C 0.5131(3) 0.9120(2) 0.29539(19) 0.0222(6) Uani 1 1 d . . .
C4' C 0.5664(3) 0.9217(3) 0.1784(2) 0.0260(6) Uani 1 1 d . . .
C3' C 0.7246(3) 0.9201(3) 0.14701(19) 0.0233(6) Uani 1 1 d . . .
C2' C 0.7917(3) 0.8025(2) 0.22311(19) 0.0207(5) Uani 1 1 d . . .
C11 C 0.7037(3) 0.4685(2) 0.31362(19) 0.0195(5) Uani 1 1 d . . .
C12 C 0.5742(3) 0.4754(3) 0.2914(2) 0.0239(6) Uani 1 1 d . . .
C13 C 0.5562(3) 0.4329(3) 0.2046(2) 0.0273(6) Uani 1 1 d . . .
C14 C 0.6711(3) 0.3842(3) 0.1377(2) 0.0248(6) Uani 1 1 d . . .
C15 C 0.8030(3) 0.3787(3) 0.1565(2) 0.0315(7) Uani 1 1 d . . .
C16 C 0.8188(3) 0.4204(3) 0.2433(2) 0.0285(6) Uani 1 1 d . . .
C17 C 0.5328(3) 0.3077(3) 0.0455(2) 0.0350(7) Uani 1 1 d . . .
H17A H 0.5404 0.2771 -0.0181 0.053 Uiso 1 1 calc R . .
H17B H 0.4655 0.3879 0.0452 0.053 Uiso 1 1 calc R . .
H17C H 0.5033 0.2378 0.1065 0.053 Uiso 1 1 calc R . .
C11' C 0.7803(3) 0.9075(2) 0.03324(19) 0.0212(6) Uani 1 1 d . . .
C12' C 0.8489(3) 1.0065(2) -0.0428(2) 0.0240(6) Uani 1 1 d . . .
C13' C 0.9044(3) 0.9910(3) -0.14651(19) 0.0224(6) Uani 1 1 d . . .
C14' C 0.8883(3) 0.8774(2) -0.17502(19) 0.0218(6) Uani 1 1 d . . .
C15' C 0.8185(3) 0.7773(3) -0.1001(2) 0.0263(6) Uani 1 1 d . . .
C16' C 0.7666(3) 0.7915(3) 0.0025(2) 0.0268(6) Uani 1 1 d . . .
C17' C 1.0191(3) 0.9432(3) -0.3513(2) 0.0335(7) Uani 1 1 d . . .
H17D H 1.0452 0.9137 -0.4168 0.050 Uiso 1 1 calc R . .
H17E H 1.1014 0.9454 -0.3263 0.050 Uiso 1 1 calc R . .
H17F H 0.9669 1.0324 -0.3628 0.050 Uiso 1 1 calc R . .


_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 1.215(3) . ?
O2' C14' 1.371(3) . ?
O2' C17' 1.418(3) . ?
O2 C14 1.384(3) . ?
O2 C17 1.431(3) . ?
C1 C9 1.503(3) . ?
C1 C2 1.531(3) . ?
C9 C10 1.393(3) . ?
C9 C8 1.402(3) . ?
C8 C7 1.387(3) . ?
C7 C6 1.383(4) . ?
C6 C5 1.390(4) . ?
C5 C10 1.395(3) . ?
C10 C4 1.497(3) . ?
C4 C3 1.535(3) . ?
C3 C11 1.518(3) . ?
C3 C2 1.553(3) . ?
C2 C1' 1.519(3) . ?
C1' C2' 1.329(3) . ?
C1' C9' 1.481(3) . ?
C9' C8' 1.391(3) . ?
C9' C10' 1.422(3) . ?
C8' C7' 1.386(4) . ?
C7' C6' 1.389(4) . ?
C6' C5' 1.385(4) . ?
C5' C10' 1.383(4) . ?
C10' C4' 1.504(4) . ?
C4' C3' 1.530(4) . ?
C3' C11' 1.515(4) . ?
C3' C2' 1.519(3) . ?
C11 C12 1.374(3) . ?
C11 C16 1.399(4) . ?
C12 C13 1.395(4) . ?
C13 C14 1.376(4) . ?
C14 C15 1.381(4) . ?
C15 C16 1.383(4) . ?
C11' C12' 1.386(3) . ?
C11' C16' 1.399(4) . ?
C12' C13' 1.399(4) . ?
C13' C14' 1.367(4) . ?
C14' C15' 1.394(3) . ?
C15' C16' 1.376(4) . ?

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
C14' O2' C17' 117.8(2) . . ?
C14 O2 C17 116.4(2) . . ?
O1 C1 C9 121.5(2) . . ?
O1 C1 C2 120.6(2) . . ?
C9 C1 C2 117.9(2) . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 C1 120.6(2) . . ?
C8 C9 C1 118.4(2) . . ?
C7 C8 C9 119.3(2) . . ?
C6 C7 C8 120.1(2) . . ?
C7 C6 C5 120.5(2) . . ?
C6 C5 C10 120.3(2) . . ?
C9 C10 C5 118.8(2) . . ?
C9 C10 C4 120.8(2) . . ?
C5 C10 C4 120.4(2) . . ?
C10 C4 C3 111.7(2) . . ?
C11 C3 C4 111.6(2) . . ?
C11 C3 C2 112.6(2) . . ?
C4 C3 C2 109.4(2) . . ?
C1' C2 C1 112.5(2) . . ?
C1' C2 C3 111.82(19) . . ?
C1 C2 C3 114.32(19) . . ?
C2' C1' C9' 120.3(2) . . ?
C2' C1' C2 119.2(2) . . ?
C9' C1' C2 120.4(2) . . ?
C8' C9' C10' 118.0(2) . . ?
C8' C9' C1' 124.2(2) . . ?
C10' C9' C1' 117.8(2) . . ?
C7' C8' C9' 121.6(2) . . ?
C8' C7' C6' 120.0(2) . . ?
C5' C6' C7' 119.3(3) . . ?
C10' C5' C6' 121.3(2) . . ?
C5' C10' C9' 119.8(2) . . ?
C5' C10' C4' 122.1(2) . . ?
C9' C10' C4' 118.0(2) . . ?
C10' C4' C3' 112.5(2) . . ?
C11' C3' C2' 110.4(2) . . ?
C11' C3' C4' 112.1(2) . . ?
C2' C3' C4' 108.2(2) . . ?
C1' C2' C3' 123.6(2) . . ?
C12 C11 C16 117.1(2) . . ?
C12 C11 C3 121.1(2) . . ?
C16 C11 C3 121.7(2) . . ?
C11 C12 C13 122.1(3) . . ?
C14 C13 C12 119.5(2) . . ?
C13 C14 O2 124.4(2) . . ?
C13 C14 C15 119.8(3) . . ?
O2 C14 C15 115.8(2) . . ?
C16 C15 C14 119.9(3) . . ?
C15 C16 C11 121.5(3) . . ?
C12' C11' C16' 117.7(2) . . ?
C12' C11' C3' 122.2(2) . . ?
C16' C11' C3' 120.0(2) . . ?
C11' C12' C13' 121.5(2) . . ?
C14' C13' C12' 119.7(2) . . ?
C13' C14' O2' 125.2(2) . . ?
C13' C14' C15' 119.7(2) . . ?
O2' C14' C15' 115.1(2) . . ?
C16' C15' C14' 120.5(2) . . ?
C15' C16' C11' 120.9(2) . . ?

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
O1 C1 C9 C10 -168.1(2) . . . . ?
C2 C1 C9 C10 10.4(3) . . . . ?
O1 C1 C9 C8 11.7(3) . . . . ?
C2 C1 C9 C8 -169.8(2) . . . . ?
C10 C9 C8 C7 -0.2(4) . . . . ?
C1 C9 C8 C7 180.0(2) . . . . ?
C9 C8 C7 C6 -0.8(4) . . . . ?
C8 C7 C6 C5 1.2(4) . . . . ?
C7 C6 C5 C10 -0.5(4) . . . . ?
C8 C9 C10 C5 0.9(4) . . . . ?
C1 C9 C10 C5 -179.3(2) . . . . ?
C8 C9 C10 C4 -179.5(2) . . . . ?
C1 C9 C10 C4 0.3(4) . . . . ?
C6 C5 C10 C9 -0.6(4) . . . . ?
C6 C5 C10 C4 179.9(3) . . . . ?
C9 C10 C4 C3 -35.1(3) . . . . ?
C5 C10 C4 C3 144.4(2) . . . . ?
C10 C4 C3 C11 -177.4(2) . . . . ?
C10 C4 C3 C2 57.2(3) . . . . ?
O1 C1 C2 C1' -38.1(3) . . . . ?
C9 C1 C2 C1' 143.4(2) . . . . ?
O1 C1 C2 C3 -167.1(2) . . . . ?
C9 C1 C2 C3 14.5(3) . . . . ?
C11 C3 C2 C1' 58.8(3) . . . . ?
C4 C3 C2 C1' -176.5(2) . . . . ?
C11 C3 C2 C1 -172.0(2) . . . . ?
C4 C3 C2 C1 -47.2(3) . . . . ?
C1 C2 C1' C2' 117.6(2) . . . . ?
C3 C2 C1' C2' -112.2(3) . . . . ?
C1 C2 C1' C9' -64.2(3) . . . . ?
C3 C2 C1' C9' 66.1(3) . . . . ?
C2' C1' C9' C8' -161.9(2) . . . . ?
C2 C1' C9' C8' 19.9(4) . . . . ?
C2' C1' C9' C10' 15.4(3) . . . . ?
C2 C1' C9' C10' -162.8(2) . . . . ?
C10' C9' C8' C7' -2.5(4) . . . . ?
C1' C9' C8' C7' 174.8(2) . . . . ?
C9' C8' C7' C6' 0.2(4) . . . . ?
C8' C7' C6' C5' 1.7(4) . . . . ?
C7' C6' C5' C10' -1.2(4) . . . . ?
C6' C5' C10' C9' -1.2(4) . . . . ?
C6' C5' C10' C4' 175.8(2) . . . . ?
C8' C9' C10' C5' 3.0(3) . . . . ?
C1' C9' C10' C5' -174.5(2) . . . . ?
C8' C9' C10' C4' -174.1(2) . . . . ?
C1' C9' C10' C4' 8.4(3) . . . . ?
C5' C10' C4' C3' 141.4(2) . . . . ?
C9' C10' C4' C3' -41.5(3) . . . . ?
C10' C4' C3' C11' 171.0(2) . . . . ?
C10' C4' C3' C2' 48.9(3) . . . . ?
C9' C1' C2' C3' -3.9(4) . . . . ?
C2 C1' C2' C3' 174.4(2) . . . . ?
C11' C3' C2' C1' -151.6(2) . . . . ?
C4' C3' C2' C1' -28.5(3) . . . . ?
C4 C3 C11 C12 118.7(3) . . . . ?
C2 C3 C11 C12 -117.9(3) . . . . ?
C4 C3 C11 C16 -58.0(3) . . . . ?
C2 C3 C11 C16 65.5(3) . . . . ?
C16 C11 C12 C13 1.9(4) . . . . ?
C3 C11 C12 C13 -174.9(2) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C12 C13 C14 O2 179.4(2) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C17 O2 C14 C13 -16.5(4) . . . . ?
C17 O2 C14 C15 163.4(2) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
O2 C14 C15 C16 -178.9(3) . . . . ?
C14 C15 C16 C11 0.0(4) . . . . ?
C12 C11 C16 C15 -1.4(4) . . . . ?
C3 C11 C16 C15 175.4(2) . . . . ?
C2' C3' C11' C12' -120.2(3) . . . . ?
C4' C3' C11' C12' 119.0(3) . . . . ?
C2' C3' C11' C16' 58.1(3) . . . . ?
C4' C3' C11' C16' -62.7(3) . . . . ?
C16' C11' C12' C13' -0.8(4) . . . . ?
C3' C11' C12' C13' 177.6(2) . . . . ?
C11' C12' C13' C14' 1.5(4) . . . . ?
C12' C13' C14' O2' 179.0(2) . . . . ?
C12' C13' C14' C15' -0.9(4) . . . . ?
C17' O2' C14' C13' 6.0(4) . . . . ?
C17' O2' C14' C15' -174.2(2) . . . . ?
C13' C14' C15' C16' -0.5(4) . . . . ?
O2' C14' C15' C16' 179.6(2) . . . . ?
C14' C15' C16' C11' 1.3(4) . . . . ?
C12' C11' C16' C15' -0.6(4) . . . . ?
C3' C11' C16' C15' -179.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.47
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 938650'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mi113-6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 O'
_chemical_formula_sum            'C20 H18 O'
_chemical_formula_weight         274.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.952(3)
_cell_length_b                   9.721(4)
_cell_length_c                   9.932(4)
_cell_angle_alpha                109.057(7)
_cell_angle_beta                 102.134(7)
_cell_angle_gamma                92.430(7)
_cell_volume                     704.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER AXS SMART APEX CCD with Mo source'
_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            3617
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         24.71
_reflns_number_total             2382
_reflns_number_gt                1866
_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    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1047P)²+0.2098P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2382
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1763
_refine_ls_wR_factor_gt          0.1522
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.002
_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
H2 H 0.384(3) 0.405(3) 0.315(3) 0.022(6) Uiso 1 1 d . . .
H20A H -0.342(3) 0.785(3) 0.521(3) 0.036(7) Uiso 1 1 d . . .
H10 H -0.408(3) 0.561(3) 0.132(3) 0.029(7) Uiso 1 1 d . . .
H4 H 0.013(3) 0.227(3) -0.068(3) 0.019(6) Uiso 1 1 d . . .
H18 H -0.656(3) 0.853(3) 0.327(3) 0.029(7) Uiso 1 1 d . . .
H16 H -0.448(3) 1.131(3) 0.160(3) 0.036(7) Uiso 1 1 d . . .
H20B H -0.432(3) 0.650(3) 0.371(3) 0.023(6) Uiso 1 1 d . . .
H9A H -0.258(3) 0.423(2) -0.066(2) 0.013(5) Uiso 1 1 d . . .
H9B H -0.319(3) 0.304(3) -0.005(3) 0.034(7) Uiso 1 1 d . . .
H17 H -0.695(3) 1.033(3) 0.208(3) 0.029(7) Uiso 1 1 d . . .
H3 H 0.301(3) 0.244(3) 0.076(3) 0.032(7) Uiso 1 1 d . . .
H12 H -0.082(3) 0.707(2) 0.481(2) 0.014(6) Uiso 1 1 d . . .
O1 O 0.0513(2) 0.87647(18) 0.35888(18) 0.0302(5) Uani 1 1 d . . .
C1 C 0.1558(3) 0.4997(3) 0.3192(3) 0.0231(6) Uani 1 1 d . . .
C11 C -0.1614(3) 0.5756(2) 0.2614(2) 0.0224(6) Uani 1 1 d . . .
C6 C -0.0117(3) 0.4930(2) 0.2321(2) 0.0215(5) Uani 1 1 d . . .
C5 C -0.0631(3) 0.3901(3) 0.0894(3) 0.0228(6) Uani 1 1 d . . .
C10 C -0.2949(3) 0.5209(3) 0.1428(3) 0.0251(6) Uani 1 1 d . . .
C19 C -0.3953(3) 0.8501(3) 0.3421(2) 0.0246(6) Uani 1 1 d . . .
C2 C 0.2643(3) 0.4006(3) 0.2546(3) 0.0259(6) Uani 1 1 d . . .
C14 C -0.2537(3) 0.9099(3) 0.3095(2) 0.0237(6) Uani 1 1 d . . .
C15 C -0.2677(3) 1.0177(3) 0.2430(3) 0.0278(6) Uani 1 1 d . . .
C17 C -0.5746(3) 1.0002(3) 0.2418(3) 0.0332(7) Uani 1 1 d . . .
C13 C -0.0993(3) 0.8412(3) 0.3549(2) 0.0246(6) Uani 1 1 d . . .
C20 C -0.3456(3) 0.7385(3) 0.4143(3) 0.0279(6) Uani 1 1 d . . .
C4 C 0.0475(3) 0.2949(3) 0.0280(3) 0.0255(6) Uani 1 1 d . . .
C9 C -0.2480(3) 0.3999(3) 0.0241(3) 0.0250(6) Uani 1 1 d . . .
C12 C -0.1622(3) 0.7090(3) 0.3922(3) 0.0244(6) Uani 1 1 d . . .
C18 C -0.5580(3) 0.8958(3) 0.3093(3) 0.0301(6) Uani 1 1 d . . .
C16 C -0.4324(3) 1.0600(3) 0.2097(3) 0.0318(6) Uani 1 1 d . . .
C3 C 0.2131(3) 0.3021(3) 0.1127(3) 0.0290(6) Uani 1 1 d . . .
C7 C 0.2209(3) 0.6038(3) 0.4736(3) 0.0281(6) Uani 1 1 d . . .
H7A H 0.3378 0.5893 0.5111 0.042 Uiso 1 1 calc R . .
H7B H 0.1486 0.5858 0.5338 0.042 Uiso 1 1 calc R . .
H7C H 0.2180 0.7028 0.4749 0.042 Uiso 1 1 calc R . .
C21 C -0.1166(4) 1.0836(3) 0.2067(3) 0.0362(7) Uani 1 1 d . . .
H21A H -0.0140 1.0430 0.2385 0.054 Uiso 1 1 calc R . .
H21B H -0.1002 1.1879 0.2557 0.054 Uiso 1 1 calc R . .
H21C H -0.1389 1.0621 0.1027 0.054 Uiso 1 1 calc R . .


_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 C13 1.220(3) . ?
C1 C2 1.408(3) . ?
C1 C6 1.413(3) . ?
C1 C7 1.501(3) . ?
C11 C10 1.347(3) . ?
C11 C6 1.490(3) . ?
C11 C12 1.508(3) . ?
C6 C5 1.404(3) . ?
C5 C4 1.389(3) . ?
C5 C9 1.498(3) . ?
C10 C9 1.493(3) . ?
C10 H10 1.00(2) . ?
C19 C14 1.390(3) . ?
C19 C18 1.393(3) . ?
C19 C20 1.508(3) . ?
C2 C3 1.383(4) . ?
C2 H2 1.00(2) . ?
C14 C15 1.406(3) . ?
C14 C13 1.480(3) . ?
C15 C16 1.395(4) . ?
C15 C21 1.501(4) . ?
C17 C18 1.384(4) . ?
C17 C16 1.391(4) . ?
C17 H17 1.04(3) . ?
C13 C12 1.541(3) . ?
C20 C12 1.545(3) . ?
C20 H20A 1.00(3) . ?
C20 H20B 0.99(3) . ?
C4 C3 1.391(3) . ?
C4 H4 0.94(2) . ?
C9 H9A 0.99(2) . ?
C9 H9B 0.99(3) . ?
C12 H12 0.98(2) . ?
C18 H18 0.95(3) . ?
C16 H16 0.97(3) . ?
C3 H3 0.97(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C2 C1 C6 116.6(2) . . ?
C2 C1 C7 119.5(2) . . ?
C6 C1 C7 123.9(2) . . ?
C10 C11 C6 108.4(2) . . ?
C10 C11 C12 124.2(2) . . ?
C6 C11 C12 127.1(2) . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 C11 107.5(2) . . ?
C1 C6 C11 132.4(2) . . ?
C4 C5 C6 122.0(2) . . ?
C4 C5 C9 128.4(2) . . ?
C6 C5 C9 109.5(2) . . ?
C11 C10 C9 111.8(2) . . ?
C11 C10 H10 124.2(14) . . ?
C9 C10 H10 123.9(14) . . ?
C14 C19 C18 120.6(2) . . ?
C14 C19 C20 111.6(2) . . ?
C18 C19 C20 127.9(2) . . ?
C3 C2 C1 122.7(2) . . ?
C3 C2 H2 119.9(13) . . ?
C1 C2 H2 117.5(13) . . ?
C19 C14 C15 122.0(2) . . ?
C19 C14 C13 109.0(2) . . ?
C15 C14 C13 129.0(2) . . ?
C16 C15 C14 116.2(2) . . ?
C16 C15 C21 120.9(2) . . ?
C14 C15 C21 122.9(2) . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 H17 121.5(14) . . ?
C16 C17 H17 117.4(14) . . ?
O1 C13 C14 127.9(2) . . ?
O1 C13 C12 124.5(2) . . ?
C14 C13 C12 107.5(2) . . ?
C19 C20 C12 104.66(19) . . ?
C19 C20 H20A 107.3(15) . . ?
C12 C20 H20A 110.3(15) . . ?
C19 C20 H20B 110.7(14) . . ?
C12 C20 H20B 113.7(14) . . ?
H20A C20 H20B 110(2) . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 H4 121.4(14) . . ?
C3 C4 H4 120.5(14) . . ?
C10 C9 C5 102.8(2) . . ?
C10 C9 H9A 112.0(12) . . ?
C5 C9 H9A 110.6(12) . . ?
C10 C9 H9B 115.1(15) . . ?
C5 C9 H9B 110.8(15) . . ?
H9A C9 H9B 105.7(19) . . ?
C11 C12 C13 105.72(19) . . ?
C11 C12 C20 113.6(2) . . ?
C13 C12 C20 103.69(19) . . ?
C11 C12 H12 111.7(13) . . ?
C13 C12 H12 108.6(13) . . ?
C20 C12 H12 112.9(12) . . ?
C17 C18 C19 118.2(2) . . ?
C17 C18 H18 120.6(16) . . ?
C19 C18 H18 121.1(16) . . ?
C17 C16 C15 122.0(2) . . ?
C17 C16 H16 119.5(16) . . ?
C15 C16 H16 118.5(16) . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 116.4(15) . . ?
C4 C3 H3 123.1(15) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C6 C5 0.6(3) . . . . ?
C7 C1 C6 C5 -178.7(2) . . . . ?
C2 C1 C6 C11 178.7(2) . . . . ?
C7 C1 C6 C11 -0.7(4) . . . . ?
C10 C11 C6 C5 1.4(3) . . . . ?
C12 C11 C6 C5 -172.0(2) . . . . ?
C10 C11 C6 C1 -176.8(2) . . . . ?
C12 C11 C6 C1 9.7(4) . . . . ?
C1 C6 C5 C4 -1.5(3) . . . . ?
C11 C6 C5 C4 -180.0(2) . . . . ?
C1 C6 C5 C9 176.9(2) . . . . ?
C11 C6 C5 C9 -1.6(2) . . . . ?
C6 C11 C10 C9 -0.7(3) . . . . ?
C12 C11 C10 C9 173.0(2) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C7 C1 C2 C3 -179.7(2) . . . . ?
C18 C19 C14 C15 0.1(4) . . . . ?
C20 C19 C14 C15 -179.3(2) . . . . ?
C18 C19 C14 C13 -179.6(2) . . . . ?
C20 C19 C14 C13 1.0(3) . . . . ?
C19 C14 C15 C16 -0.9(3) . . . . ?
C13 C14 C15 C16 178.8(2) . . . . ?
C19 C14 C15 C21 -179.9(2) . . . . ?
C13 C14 C15 C21 -0.3(4) . . . . ?
C19 C14 C13 O1 -171.1(2) . . . . ?
C15 C14 C13 O1 9.2(4) . . . . ?
C19 C14 C13 C12 11.1(3) . . . . ?
C15 C14 C13 C12 -168.6(2) . . . . ?
C14 C19 C20 C12 -12.4(3) . . . . ?
C18 C19 C20 C12 168.2(2) . . . . ?
C6 C5 C4 C3 0.8(3) . . . . ?
C9 C5 C4 C3 -177.2(2) . . . . ?
C11 C10 C9 C5 -0.3(3) . . . . ?
C4 C5 C9 C10 179.4(2) . . . . ?
C6 C5 C9 C10 1.2(2) . . . . ?
C10 C11 C12 C13 -87.3(3) . . . . ?
C6 C11 C12 C13 85.2(3) . . . . ?
C10 C11 C12 C20 25.7(3) . . . . ?
C6 C11 C12 C20 -161.8(2) . . . . ?
O1 C13 C12 C11 -76.2(3) . . . . ?
C14 C13 C12 C11 101.7(2) . . . . ?
O1 C13 C12 C20 164.1(2) . . . . ?
C14 C13 C12 C20 -18.0(2) . . . . ?
C19 C20 C12 C11 -96.3(2) . . . . ?
C19 C20 C12 C13 17.9(2) . . . . ?
C16 C17 C18 C19 -1.1(4) . . . . ?
C14 C19 C18 C17 0.9(4) . . . . ?
C20 C19 C18 C17 -179.8(2) . . . . ?
C18 C17 C16 C15 0.3(4) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C21 C15 C16 C17 179.8(2) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
C5 C4 C3 C2 0.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 980068'
