# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

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#
#                 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.
#
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#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_mo_dlb349_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H24 O3'
_chemical_formula_weight         456.51

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   Cc

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.5702(14)
_cell_length_b                   24.243(6)
_cell_length_c                   17.573(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.744(10)
_cell_angle_gamma                90.00
_cell_volume                     2368.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2132
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      23.25

_exptl_crystal_description       needles
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            15211
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0986
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         28.11
_reflns_number_total             5364
_reflns_number_gt                3561
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0596P)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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   0.8(14)
_refine_ls_number_reflns         5364
_refine_ls_number_parameters     318
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.007
_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 0.2504(4) 0.06242(8) 0.20685(12) 0.0235(5) Uani 1 1 d . . .
O2 O 0.4126(4) 0.02471(8) 0.31532(13) 0.0304(5) Uani 1 1 d . . .
O3 O 1.0086(4) 0.25253(9) 0.13128(13) 0.0285(5) Uani 1 1 d . . .
C1 C 0.4073(5) 0.10710(11) 0.21466(17) 0.0213(7) Uani 1 1 d . . .
C2 C 0.4250(5) 0.14309(12) 0.28037(17) 0.0221(7) Uani 1 1 d . . .
H2 H 0.3404 0.1387 0.3252 0.026 Uiso 1 1 calc R . .
C3 C 0.5820(5) 0.18412(11) 0.26742(17) 0.0196(6) Uani 1 1 d . . .
C4 C 0.6701(5) 0.17708(11) 0.18834(16) 0.0193(6) Uani 1 1 d . . .
H4 H 0.8489 0.1726 0.1917 0.023 Uiso 1 1 calc R . .
C5 C 0.5508(5) 0.12381(11) 0.16049(16) 0.0192(6) Uani 1 1 d . . .
C6 C 0.2670(6) 0.02252(12) 0.26205(17) 0.0220(7) Uani 1 1 d . . .
C7 C 0.0914(6) -0.02237(12) 0.24568(16) 0.0211(6) Uani 1 1 d . . .
C8 C -0.1077(5) -0.01530(13) 0.19430(19) 0.0291(8) Uani 1 1 d . . .
H8 H -0.1325 0.0187 0.1680 0.035 Uiso 1 1 calc R . .
C9 C -0.2682(7) -0.05810(14) 0.1821(2) 0.0373(9) Uani 1 1 d . . .
H9 H -0.4055 -0.0535 0.1477 0.045 Uiso 1 1 calc R . .
C10 C -0.2302(6) -0.10805(13) 0.2197(2) 0.0351(9) Uani 1 1 d . . .
H10 H -0.3419 -0.1373 0.2110 0.042 Uiso 1 1 calc R . .
C11 C -0.0331(6) -0.11536(12) 0.26929(18) 0.0286(7) Uani 1 1 d . . .
H11 H -0.0062 -0.1498 0.2942 0.034 Uiso 1 1 calc R . .
C12 C 0.1273(6) -0.07217(12) 0.28296(17) 0.0249(7) Uani 1 1 d . . .
H12 H 0.2626 -0.0768 0.3182 0.030 Uiso 1 1 calc R . .
C13 C 0.6585(5) 0.22844(11) 0.32001(17) 0.0194(6) Uani 1 1 d . . .
C14 C 0.5241(5) 0.24143(11) 0.38185(18) 0.0221(7) Uani 1 1 d . . .
H14 H 0.3792 0.2219 0.3888 0.026 Uiso 1 1 calc R . .
C15 C 0.5981(6) 0.28212(12) 0.43316(18) 0.0245(7) Uani 1 1 d . . .
H15 H 0.5051 0.2902 0.4752 0.029 Uiso 1 1 calc R . .
C16 C 0.8080(5) 0.31123(12) 0.42339(18) 0.0232(7) Uani 1 1 d . . .
H16 H 0.8584 0.3394 0.4585 0.028 Uiso 1 1 calc R . .
C17 C 0.9434(6) 0.29914(11) 0.36258(17) 0.0226(7) Uani 1 1 d . . .
H17 H 1.0872 0.3191 0.3558 0.027 Uiso 1 1 calc R . .
C18 C 0.8709(5) 0.25789(12) 0.31104(18) 0.0231(7) Uani 1 1 d . . .
H18 H 0.9661 0.2497 0.2696 0.028 Uiso 1 1 calc R . .
C19 C 0.5975(5) 0.22570(11) 0.13451(17) 0.0206(6) Uani 1 1 d . . .
H19A H 0.5127 0.2105 0.0879 0.025 Uiso 1 1 calc R . .
H19B H 0.4815 0.2492 0.1600 0.025 Uiso 1 1 calc R . .
C20 C 0.7998(5) 0.26180(11) 0.11084(17) 0.0193(6) Uani 1 1 d . . .
C21 C 0.7349(5) 0.30918(12) 0.05940(16) 0.0220(7) Uani 1 1 d . . .
C22 C 0.9090(6) 0.34951(12) 0.0493(2) 0.0317(8) Uani 1 1 d . . .
H22 H 1.0629 0.3466 0.0757 0.038 Uiso 1 1 calc R . .
C23 C 0.8580(7) 0.39378(14) 0.0009(2) 0.0380(9) Uani 1 1 d . . .
H23 H 0.9765 0.4213 -0.0053 0.046 Uiso 1 1 calc R . .
C24 C 0.6367(6) 0.39802(13) -0.03804(19) 0.0318(8) Uani 1 1 d . . .
H24 H 0.6016 0.4288 -0.0703 0.038 Uiso 1 1 calc R . .
C25 C 0.4657(6) 0.35772(13) -0.0304(2) 0.0321(8) Uani 1 1 d . . .
H25 H 0.3151 0.3600 -0.0588 0.039 Uiso 1 1 calc R . .
C26 C 0.5138(6) 0.31383(13) 0.01906(18) 0.0273(7) Uani 1 1 d . . .
H26 H 0.3937 0.2867 0.0253 0.033 Uiso 1 1 calc R . .
C27 C 0.5906(5) 0.09907(11) 0.08612(17) 0.0190(6) Uani 1 1 d . . .
C28 C 0.7964(5) 0.11220(12) 0.04877(16) 0.0222(7) Uani 1 1 d . . .
H28 H 0.9110 0.1369 0.0723 0.027 Uiso 1 1 calc R . .
C29 C 0.8375(6) 0.08994(12) -0.02203(18) 0.0250(7) Uani 1 1 d . . .
H29 H 0.9786 0.0996 -0.0465 0.030 Uiso 1 1 calc R . .
C30 C 0.6737(6) 0.05380(12) -0.05678(17) 0.0246(7) Uani 1 1 d . . .
H30 H 0.7013 0.0383 -0.1051 0.030 Uiso 1 1 calc R . .
C31 C 0.4685(5) 0.04031(12) -0.02043(17) 0.0229(7) Uani 1 1 d . . .
H31 H 0.3547 0.0157 -0.0446 0.027 Uiso 1 1 calc R . .
C32 C 0.4255(5) 0.06178(11) 0.05003(17) 0.0206(6) Uani 1 1 d . . .
H32 H 0.2847 0.0515 0.0743 0.025 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 C6 1.369(3) . ?
O1 C1 1.393(3) . ?
O2 C6 1.199(3) . ?
O3 C20 1.215(3) . ?
C1 C5 1.345(4) . ?
C1 C2 1.445(4) . ?
C2 C3 1.354(4) . ?
C3 C13 1.462(4) . ?
C3 C4 1.513(4) . ?
C4 C5 1.519(4) . ?
C4 C19 1.548(4) . ?
C5 C27 1.468(4) . ?
C6 C7 1.479(4) . ?
C7 C12 1.382(4) . ?
C7 C8 1.394(4) . ?
C8 C9 1.377(4) . ?
C9 C10 1.390(5) . ?
C10 C11 1.367(5) . ?
C11 C12 1.387(4) . ?
C13 C14 1.395(4) . ?
C13 C18 1.400(4) . ?
C14 C15 1.381(4) . ?
C15 C16 1.386(4) . ?
C16 C17 1.379(4) . ?
C17 C18 1.391(4) . ?
C19 C20 1.507(4) . ?
C20 C21 1.491(4) . ?
C21 C26 1.385(4) . ?
C21 C22 1.396(4) . ?
C22 C23 1.387(5) . ?
C23 C24 1.374(5) . ?
C24 C25 1.377(5) . ?
C25 C26 1.389(4) . ?
C27 C28 1.394(4) . ?
C27 C32 1.410(4) . ?
C28 C29 1.389(4) . ?
C29 C30 1.379(4) . ?
C30 C31 1.385(4) . ?
C31 C32 1.378(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
C6 O1 C1 117.8(2) . . ?
C5 C1 O1 124.2(3) . . ?
C5 C1 C2 111.8(2) . . ?
O1 C1 C2 123.9(3) . . ?
C3 C2 C1 108.7(3) . . ?
C2 C3 C13 126.8(3) . . ?
C2 C3 C4 108.9(2) . . ?
C13 C3 C4 124.4(3) . . ?
C3 C4 C5 103.3(2) . . ?
C3 C4 C19 112.8(2) . . ?
C5 C4 C19 111.1(2) . . ?
C1 C5 C27 129.7(3) . . ?
C1 C5 C4 107.2(2) . . ?
C27 C5 C4 123.1(2) . . ?
O2 C6 O1 122.2(3) . . ?
O2 C6 C7 126.1(3) . . ?
O1 C6 C7 111.6(2) . . ?
C12 C7 C8 119.9(3) . . ?
C12 C7 C6 118.5(3) . . ?
C8 C7 C6 121.6(3) . . ?
C9 C8 C7 119.3(3) . . ?
C8 C9 C10 120.3(3) . . ?
C11 C10 C9 120.5(3) . . ?
C10 C11 C12 119.6(3) . . ?
C7 C12 C11 120.4(3) . . ?
C14 C13 C18 118.2(3) . . ?
C14 C13 C3 120.6(3) . . ?
C18 C13 C3 121.1(3) . . ?
C15 C14 C13 121.1(3) . . ?
C14 C15 C16 120.1(3) . . ?
C17 C16 C15 119.8(3) . . ?
C16 C17 C18 120.5(3) . . ?
C17 C18 C13 120.3(3) . . ?
C20 C19 C4 116.2(2) . . ?
O3 C20 C21 120.7(3) . . ?
O3 C20 C19 122.0(3) . . ?
C21 C20 C19 117.3(2) . . ?
C26 C21 C22 118.6(3) . . ?
C26 C21 C20 123.0(3) . . ?
C22 C21 C20 118.3(3) . . ?
C23 C22 C21 120.2(3) . . ?
C24 C23 C22 120.3(3) . . ?
C23 C24 C25 120.1(3) . . ?
C24 C25 C26 119.9(3) . . ?
C21 C26 C25 120.8(3) . . ?
C28 C27 C32 117.8(3) . . ?
C28 C27 C5 120.2(3) . . ?
C32 C27 C5 122.0(3) . . ?
C29 C28 C27 121.4(3) . . ?
C30 C29 C28 120.1(3) . . ?
C29 C30 C31 119.2(3) . . ?
C32 C31 C30 121.5(3) . . ?
C31 C32 C27 120.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 O1 C1 C5 126.6(3) . . . . ?
C6 O1 C1 C2 -57.2(4) . . . . ?
C5 C1 C2 C3 0.6(4) . . . . ?
O1 C1 C2 C3 -176.0(3) . . . . ?
C1 C2 C3 C13 -177.9(3) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?
C2 C3 C4 C5 -3.4(3) . . . . ?
C13 C3 C4 C5 176.4(3) . . . . ?
C2 C3 C4 C19 116.6(3) . . . . ?
C13 C3 C4 C19 -63.6(4) . . . . ?
O1 C1 C5 C27 -4.5(5) . . . . ?
C2 C1 C5 C27 178.9(3) . . . . ?
O1 C1 C5 C4 173.8(3) . . . . ?
C2 C1 C5 C4 -2.8(3) . . . . ?
C3 C4 C5 C1 3.7(3) . . . . ?
C19 C4 C5 C1 -117.5(3) . . . . ?
C3 C4 C5 C27 -177.9(2) . . . . ?
C19 C4 C5 C27 60.9(3) . . . . ?
C1 O1 C6 O2 -1.0(4) . . . . ?
C1 O1 C6 C7 -179.4(2) . . . . ?
O2 C6 C7 C12 -16.0(5) . . . . ?
O1 C6 C7 C12 162.4(3) . . . . ?
O2 C6 C7 C8 163.6(3) . . . . ?
O1 C6 C7 C8 -18.0(4) . . . . ?
C12 C7 C8 C9 0.8(5) . . . . ?
C6 C7 C8 C9 -178.9(3) . . . . ?
C7 C8 C9 C10 -0.9(5) . . . . ?
C8 C9 C10 C11 -0.1(6) . . . . ?
C9 C10 C11 C12 1.2(6) . . . . ?
C8 C7 C12 C11 0.3(5) . . . . ?
C6 C7 C12 C11 180.0(3) . . . . ?
C10 C11 C12 C7 -1.3(5) . . . . ?
C2 C3 C13 C14 -18.2(4) . . . . ?
C4 C3 C13 C14 162.1(3) . . . . ?
C2 C3 C13 C18 160.1(3) . . . . ?
C4 C3 C13 C18 -19.7(4) . . . . ?
C18 C13 C14 C15 -0.2(4) . . . . ?
C3 C13 C14 C15 178.1(3) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C13 0.5(4) . . . . ?
C14 C13 C18 C17 -0.4(4) . . . . ?
C3 C13 C18 C17 -178.6(3) . . . . ?
C3 C4 C19 C20 112.0(3) . . . . ?
C5 C4 C19 C20 -132.5(3) . . . . ?
C4 C19 C20 O3 1.7(4) . . . . ?
C4 C19 C20 C21 -179.6(3) . . . . ?
O3 C20 C21 C26 163.1(3) . . . . ?
C19 C20 C21 C26 -15.6(4) . . . . ?
O3 C20 C21 C22 -14.3(4) . . . . ?
C19 C20 C21 C22 167.0(3) . . . . ?
C26 C21 C22 C23 1.3(5) . . . . ?
C20 C21 C22 C23 178.8(3) . . . . ?
C21 C22 C23 C24 -0.7(5) . . . . ?
C22 C23 C24 C25 -1.2(5) . . . . ?
C23 C24 C25 C26 2.4(5) . . . . ?
C22 C21 C26 C25 -0.1(5) . . . . ?
C20 C21 C26 C25 -177.5(3) . . . . ?
C24 C25 C26 C21 -1.8(5) . . . . ?
C1 C5 C27 C28 -160.2(3) . . . . ?
C4 C5 C27 C28 21.8(4) . . . . ?
C1 C5 C27 C32 19.9(4) . . . . ?
C4 C5 C27 C32 -158.1(3) . . . . ?
C32 C27 C28 C29 0.7(4) . . . . ?
C5 C27 C28 C29 -179.2(3) . . . . ?
C27 C28 C29 C30 -0.3(4) . . . . ?
C28 C29 C30 C31 0.3(4) . . . . ?
C29 C30 C31 C32 -0.6(4) . . . . ?
C30 C31 C32 C27 1.0(4) . . . . ?
C28 C27 C32 C31 -1.0(4) . . . . ?
C5 C27 C32 C31 178.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.11
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 1000511'
#######################################################################
#
#                 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_mo_wyh8_100_1_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H22 O'
_chemical_formula_weight         410.49

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                   11.2685(19)
_cell_length_b                   9.1961(15)
_cell_length_c                   20.509(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.368(6)
_cell_angle_gamma                90.00
_cell_volume                     2123.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2590
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      23.58

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9623
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            17032
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.09
_reflns_number_total             3760
_reflns_number_gt                2375
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0640P)²+1.0494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3760
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.38302(17) 0.3180(2) 0.13185(11) 0.0355(6) Uani 1 1 d . . .
C1 C 0.2910(3) 0.4809(3) 0.05603(14) 0.0246(7) Uani 1 1 d . . .
C2 C 0.1940(3) 0.4988(3) 0.01269(14) 0.0289(7) Uani 1 1 d . . .
H2 H 0.1238 0.4436 0.0180 0.035 Uiso 1 1 calc R . .
C3 C 0.1995(3) 0.5970(4) -0.03814(16) 0.0370(8) Uani 1 1 d . . .
H3 H 0.1338 0.6067 -0.0684 0.044 Uiso 1 1 calc R . .
C4 C 0.2996(3) 0.6811(3) -0.04543(16) 0.0371(9) Uani 1 1 d . . .
H4 H 0.3021 0.7494 -0.0801 0.045 Uiso 1 1 calc R . .
C5 C 0.3963(3) 0.6658(3) -0.00210(16) 0.0355(8) Uani 1 1 d . . .
H5 H 0.4652 0.7235 -0.0070 0.043 Uiso 1 1 calc R . .
C6 C 0.3922(3) 0.5658(3) 0.04845(16) 0.0310(8) Uani 1 1 d . . .
H6 H 0.4587 0.5551 0.0781 0.037 Uiso 1 1 calc R . .
C7 C 0.2901(3) 0.3707(3) 0.10896(15) 0.0263(7) Uani 1 1 d . . .
C8 C 0.1735(2) 0.3275(3) 0.13633(13) 0.0219(7) Uani 1 1 d . . .
C9 C 0.0968(2) 0.4379(3) 0.15557(14) 0.0250(7) Uani 1 1 d . . .
H9 H 0.1164 0.5368 0.1479 0.030 Uiso 1 1 calc R . .
C10 C -0.0075(3) 0.4036(3) 0.18572(14) 0.0285(7) Uani 1 1 d . . .
H10 H -0.0591 0.4788 0.1989 0.034 Uiso 1 1 calc R . .
C11 C -0.0360(3) 0.2607(3) 0.19650(15) 0.0286(7) Uani 1 1 d . . .
H11 H -0.1075 0.2370 0.2171 0.034 Uiso 1 1 calc R . .
C12 C 0.0393(2) 0.1508(3) 0.17737(14) 0.0256(7) Uani 1 1 d . . .
H12 H 0.0191 0.0523 0.1854 0.031 Uiso 1 1 calc R . .
C13 C 0.1441(2) 0.1824(3) 0.14667(13) 0.0214(7) Uani 1 1 d . . .
C14 C 0.2175(2) 0.0582(3) 0.12395(14) 0.0225(7) Uani 1 1 d . . .
C15 C 0.2332(2) 0.0294(3) 0.06056(14) 0.0240(7) Uani 1 1 d . . .
H15 H 0.2870 -0.0473 0.0522 0.029 Uiso 1 1 calc R . .
C16 C 0.1787(2) 0.1001(3) 0.00238(14) 0.0224(7) Uani 1 1 d . . .
C17 C 0.0635(2) 0.1510(3) 0.00075(15) 0.0250(7) Uani 1 1 d . . .
H17 H 0.0206 0.1493 0.0396 0.030 Uiso 1 1 calc R . .
C18 C 0.0081(3) 0.2052(3) -0.05641(15) 0.0276(7) Uani 1 1 d . . .
H18 H -0.0707 0.2417 -0.0556 0.033 Uiso 1 1 calc R . .
C19 C 0.0666(3) 0.2060(3) -0.11331(15) 0.0277(7) Uani 1 1 d . . .
H19 H 0.0276 0.2412 -0.1521 0.033 Uiso 1 1 calc R . .
C20 C 0.1847(3) 0.1548(3) -0.11516(15) 0.0272(7) Uani 1 1 d . . .
C21 C 0.2452(3) 0.1509(3) -0.17397(15) 0.0334(8) Uani 1 1 d . . .
H21 H 0.2050 0.1805 -0.2134 0.040 Uiso 1 1 calc R . .
C22 C 0.3606(3) 0.1055(4) -0.17535(17) 0.0374(8) Uani 1 1 d . . .
H22 H 0.4008 0.1060 -0.2152 0.045 Uiso 1 1 calc R . .
C23 C 0.4192(3) 0.0578(4) -0.11739(16) 0.0359(8) Uani 1 1 d . . .
H23 H 0.4991 0.0252 -0.1182 0.043 Uiso 1 1 calc R . .
C24 C 0.3622(2) 0.0581(3) -0.06010(15) 0.0297(8) Uani 1 1 d . . .
H24 H 0.4038 0.0271 -0.0214 0.036 Uiso 1 1 calc R . .
C25 C 0.2427(2) 0.1034(3) -0.05675(14) 0.0248(7) Uani 1 1 d . . .
C26 C 0.2719(2) -0.0378(3) 0.17555(14) 0.0235(7) Uani 1 1 d . . .
C27 C 0.2829(2) -0.1876(3) 0.16623(15) 0.0262(7) Uani 1 1 d . . .
H27 H 0.2527 -0.2301 0.1267 0.031 Uiso 1 1 calc R . .
C28 C 0.3370(3) -0.2746(3) 0.21330(15) 0.0294(8) Uani 1 1 d . . .
H28 H 0.3448 -0.3759 0.2056 0.035 Uiso 1 1 calc R . .
C29 C 0.3802(3) -0.2155(3) 0.27190(15) 0.0292(7) Uani 1 1 d . . .
H29 H 0.4172 -0.2756 0.3045 0.035 Uiso 1 1 calc R . .
C30 C 0.3685(3) -0.0686(4) 0.28186(15) 0.0322(8) Uani 1 1 d . . .
H30 H 0.3977 -0.0268 0.3217 0.039 Uiso 1 1 calc R . .
C31 C 0.3148(3) 0.0192(3) 0.23451(14) 0.0283(7) Uani 1 1 d . . .
H31 H 0.3071 0.1205 0.2425 0.034 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 C7 1.230(3) . ?
C1 C2 1.390(4) . ?
C1 C6 1.396(4) . ?
C1 C7 1.485(4) . ?
C2 C3 1.383(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.384(5) . ?
C5 C6 1.388(4) . ?
C7 C8 1.504(4) . ?
C8 C13 1.393(4) . ?
C8 C9 1.400(4) . ?
C9 C10 1.387(4) . ?
C10 C11 1.373(4) . ?
C11 C12 1.387(4) . ?
C12 C13 1.391(4) . ?
C13 C14 1.496(4) . ?
C14 C15 1.346(4) . ?
C14 C26 1.490(4) . ?
C15 C16 1.471(4) . ?
C16 C17 1.379(4) . ?
C16 C25 1.437(4) . ?
C17 C18 1.397(4) . ?
C18 C19 1.364(4) . ?
C19 C20 1.413(4) . ?
C20 C21 1.410(4) . ?
C20 C25 1.422(4) . ?
C21 C22 1.367(4) . ?
C22 C23 1.406(4) . ?
C23 C24 1.362(4) . ?
C24 C25 1.414(4) . ?
C26 C31 1.387(4) . ?
C26 C27 1.397(4) . ?
C27 C28 1.376(4) . ?
C28 C29 1.389(4) . ?
C29 C30 1.373(4) . ?
C30 C31 1.383(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
C2 C1 C6 119.1(3) . . ?
C2 C1 C7 121.3(3) . . ?
C6 C1 C7 119.6(3) . . ?
C3 C2 C1 120.0(3) . . ?
C4 C3 C2 120.7(3) . . ?
C3 C4 C5 119.9(3) . . ?
C4 C5 C6 119.8(3) . . ?
C5 C6 C1 120.4(3) . . ?
O1 C7 C1 121.1(3) . . ?
O1 C7 C8 119.8(3) . . ?
C1 C7 C8 119.1(2) . . ?
C13 C8 C9 119.9(3) . . ?
C13 C8 C7 121.8(2) . . ?
C9 C8 C7 118.2(3) . . ?
C10 C9 C8 120.3(3) . . ?
C11 C10 C9 119.9(3) . . ?
C10 C11 C12 120.1(3) . . ?
C11 C12 C13 121.2(3) . . ?
C12 C13 C8 118.7(3) . . ?
C12 C13 C14 118.2(3) . . ?
C8 C13 C14 123.1(2) . . ?
C15 C14 C26 120.2(3) . . ?
C15 C14 C13 123.2(3) . . ?
C26 C14 C13 116.6(2) . . ?
C14 C15 C16 129.0(3) . . ?
C17 C16 C25 118.5(3) . . ?
C17 C16 C15 122.1(3) . . ?
C25 C16 C15 119.1(3) . . ?
C16 C17 C18 122.0(3) . . ?
C19 C18 C17 120.3(3) . . ?
C18 C19 C20 120.7(3) . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 C25 119.4(3) . . ?
C19 C20 C25 119.2(3) . . ?
C22 C21 C20 121.3(3) . . ?
C21 C22 C23 119.5(3) . . ?
C24 C23 C22 120.4(3) . . ?
C23 C24 C25 121.8(3) . . ?
C24 C25 C20 117.5(3) . . ?
C24 C25 C16 123.2(3) . . ?
C20 C25 C16 119.3(3) . . ?
C31 C26 C27 117.5(3) . . ?
C31 C26 C14 120.9(3) . . ?
C27 C26 C14 121.6(3) . . ?
C28 C27 C26 121.1(3) . . ?
C27 C28 C29 120.6(3) . . ?
C30 C29 C28 118.8(3) . . ?
C29 C30 C31 120.8(3) . . ?
C30 C31 C26 121.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.7(5) . . . . ?
C7 C1 C2 C3 -176.7(3) . . . . ?
C1 C2 C3 C4 -1.9(5) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C7 C1 C6 C5 177.8(3) . . . . ?
C2 C1 C7 O1 154.0(3) . . . . ?
C6 C1 C7 O1 -24.4(4) . . . . ?
C2 C1 C7 C8 -28.1(4) . . . . ?
C6 C1 C7 C8 153.5(3) . . . . ?
O1 C7 C8 C13 -48.0(4) . . . . ?
C1 C7 C8 C13 134.1(3) . . . . ?
O1 C7 C8 C9 127.8(3) . . . . ?
C1 C7 C8 C9 -50.0(4) . . . . ?
C13 C8 C9 C10 0.9(4) . . . . ?
C7 C8 C9 C10 -175.0(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C11 C12 C13 C8 1.1(4) . . . . ?
C11 C12 C13 C14 -176.5(3) . . . . ?
C9 C8 C13 C12 -1.3(4) . . . . ?
C7 C8 C13 C12 174.5(3) . . . . ?
C9 C8 C13 C14 176.2(3) . . . . ?
C7 C8 C13 C14 -8.0(4) . . . . ?
C12 C13 C14 C15 112.8(3) . . . . ?
C8 C13 C14 C15 -64.8(4) . . . . ?
C12 C13 C14 C26 -65.7(3) . . . . ?
C8 C13 C14 C26 116.8(3) . . . . ?
C26 C14 C15 C16 173.3(3) . . . . ?
C13 C14 C15 C16 -5.1(5) . . . . ?
C14 C15 C16 C17 -35.0(5) . . . . ?
C14 C15 C16 C25 151.3(3) . . . . ?
C25 C16 C17 C18 0.0(4) . . . . ?
C15 C16 C17 C18 -173.6(3) . . . . ?
C16 C17 C18 C19 1.5(4) . . . . ?
C17 C18 C19 C20 -1.3(4) . . . . ?
C18 C19 C20 C21 178.1(3) . . . . ?
C18 C19 C20 C25 -0.5(4) . . . . ?
C19 C20 C21 C22 178.0(3) . . . . ?
C25 C20 C21 C22 -3.3(5) . . . . ?
C20 C21 C22 C23 1.8(5) . . . . ?
C21 C22 C23 C24 -0.6(5) . . . . ?
C22 C23 C24 C25 1.1(5) . . . . ?
C23 C24 C25 C20 -2.5(4) . . . . ?
C23 C24 C25 C16 177.7(3) . . . . ?
C21 C20 C25 C24 3.6(4) . . . . ?
C19 C20 C25 C24 -177.7(3) . . . . ?
C21 C20 C25 C16 -176.6(3) . . . . ?
C19 C20 C25 C16 2.1(4) . . . . ?
C17 C16 C25 C24 178.0(3) . . . . ?
C15 C16 C25 C24 -8.2(4) . . . . ?
C17 C16 C25 C20 -1.8(4) . . . . ?
C15 C16 C25 C20 172.1(3) . . . . ?
C15 C14 C26 C31 144.5(3) . . . . ?
C13 C14 C26 C31 -37.0(4) . . . . ?
C15 C14 C26 C27 -34.7(4) . . . . ?
C13 C14 C26 C27 143.8(3) . . . . ?
C31 C26 C27 C28 -1.5(4) . . . . ?
C14 C26 C27 C28 177.7(3) . . . . ?
C26 C27 C28 C29 1.1(4) . . . . ?
C27 C28 C29 C30 -0.3(4) . . . . ?
C28 C29 C30 C31 0.0(5) . . . . ?
C29 C30 C31 C26 -0.4(5) . . . . ?
C27 C26 C31 C30 1.1(4) . . . . ?
C14 C26 C31 C30 -178.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 1000512'
