# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 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 
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#  data retrieval see:
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#
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#  from this site to visualise CIF-encoded structures and 
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data_110927a_0m
_database_code_depnum_ccdc_archive 'CCDC 893966'
#TrackingRef '110927a_0m.cif'




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C26 H18 O'

_chemical_formula_weight         346.40




_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




_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                   11.9746(15)

_cell_length_b                   9.4799(12)

_cell_length_c                   19.8636(19)

_cell_angle_alpha                90.00

_cell_angle_beta                 125.669(5)

_cell_angle_gamma                90.00

_cell_volume                     1831.9(4)

_cell_formula_units_Z            4

_cell_measurement_temperature    150(2)

_cell_measurement_reflns_used    2295

_cell_measurement_theta_min      2.52

_cell_measurement_theta_max      27.56



_exptl_crystal_description       ?

_exptl_crystal_colour            ?

_exptl_crystal_size_max          0.57

_exptl_crystal_size_mid          0.43

_exptl_crystal_size_min          0.40

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.256

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             728

_exptl_absorpt_coefficient_mu    0.075

_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_correction_T_min  0.9586

_exptl_absorpt_correction_T_max  0.9707

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

?

;



_diffrn_ambient_temperature      150(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            10566

_diffrn_reflns_av_R_equivalents  0.0354

_diffrn_reflns_av_sigmaI/netI    0.0448

_diffrn_reflns_limit_h_min       -15

_diffrn_reflns_limit_h_max       15

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -20

_diffrn_reflns_limit_l_max       25

_diffrn_reflns_theta_min         2.49

_diffrn_reflns_theta_max         27.62

_reflns_number_total             4208

_reflns_number_gt                3150

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F^2^, conventional R-factors R are based

on F, with F set to zero for negative F^2^. The threshold expression of

F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F^2^ are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+0.3043P] 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         4208

_refine_ls_number_parameters     244

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0649

_refine_ls_R_factor_gt           0.0456

_refine_ls_wR_factor_ref         0.1092

_refine_ls_wR_factor_gt          0.0994

_refine_ls_goodness_of_fit_ref   1.045

_refine_ls_restrained_S_all      1.045

_refine_ls_shift/su_max          0.001

_refine_ls_shift/su_mean         0.000




_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 0.61507(10) 0.43098(10) 0.97587(6) 0.0293(2) Uani 1 1 d . . .
C1 C 0.80758(16) 0.36157(16) 0.75159(9) 0.0321(3) Uani 1 1 d . . .
H1 H 0.8970 0.4009 0.7789 0.038 Uiso 1 1 calc R . .
C2 C 0.76057(18) 0.26564(16) 0.68739(10) 0.0379(4) Uani 1 1 d . . .
H2 H 0.8190 0.2382 0.6719 0.045 Uiso 1 1 calc R . .
C3 C 0.62945(17) 0.20973(16) 0.64575(9) 0.0366(4) Uani 1 1 d . . .
H3 H 0.5984 0.1436 0.6023 0.044 Uiso 1 1 calc R . .
C4 C 0.54431(16) 0.25049(15) 0.66766(9) 0.0336(3) Uani 1 1 d . . .
H4 H 0.4538 0.2134 0.6388 0.040 Uiso 1 1 calc R . .
C5 C 0.59059(14) 0.34559(15) 0.73187(9) 0.0290(3) Uani 1 1 d . . .
H5 H 0.5307 0.3741 0.7461 0.035 Uiso 1 1 calc R . .
C6 C 0.72351(14) 0.40000(14) 0.77586(8) 0.0240(3) Uani 1 1 d . . .
C7 C 0.77089(13) 0.50071(14) 0.84553(8) 0.0232(3) Uani 1 1 d . . .
C8 C 0.80453(14) 0.64374(14) 0.82957(8) 0.0236(3) Uani 1 1 d . . .
C9 C 0.69764(15) 0.72919(15) 0.76903(8) 0.0275(3) Uani 1 1 d . . .
H9 H 0.6055 0.6966 0.7397 0.033 Uiso 1 1 calc R . .
C10 C 0.72425(16) 0.86117(16) 0.75112(9) 0.0336(3) Uani 1 1 d . . .
H10 H 0.6505 0.9191 0.7105 0.040 Uiso 1 1 calc R . .
C11 C 0.85862(17) 0.90837(16) 0.79261(9) 0.0351(4) Uani 1 1 d . . .
H11 H 0.8771 0.9989 0.7807 0.042 Uiso 1 1 calc R . .
C12 C 0.96530(16) 0.82343(16) 0.85116(10) 0.0349(4) Uani 1 1 d . . .
H12 H 1.0574 0.8556 0.8794 0.042 Uiso 1 1 calc R . .
C13 C 0.93910(15) 0.69114(15) 0.86916(9) 0.0302(3) Uani 1 1 d . . .
H13 H 1.0135 0.6326 0.9087 0.036 Uiso 1 1 calc R . .
C14 C 0.76799(13) 0.46677(13) 0.91094(8) 0.0223(3) Uani 1 1 d . . .
C15 C 0.78554(13) 0.56692(13) 0.97425(8) 0.0230(3) Uani 1 1 d . . .
C16 C 0.87466(14) 0.68337(14) 1.00790(9) 0.0277(3) Uani 1 1 d . . .
H16 H 0.9344 0.7007 0.9920 0.033 Uiso 1 1 calc R . .
C17 C 0.87756(16) 0.77338(15) 1.06373(9) 0.0329(3) Uani 1 1 d . . .
H17 H 0.9377 0.8524 1.0847 0.039 Uiso 1 1 calc R . .
C18 C 0.79339(16) 0.74925(15) 1.08942(9) 0.0341(4) Uani 1 1 d . . .
H18 H 0.7951 0.8120 1.1273 0.041 Uiso 1 1 calc R . .
C19 C 0.70708(15) 0.63342(15) 1.05954(9) 0.0306(3) Uani 1 1 d . . .
H19 H 0.6498 0.6151 1.0771 0.037 Uiso 1 1 calc R . .
C20 C 0.70535(14) 0.54418(14) 1.00339(8) 0.0252(3) Uani 1 1 d . . .
C21 C 0.65352(14) 0.31149(14) 0.95365(8) 0.0253(3) Uani 1 1 d . . .
C22 C 0.60894(15) 0.18289(15) 0.96325(9) 0.0305(3) Uani 1 1 d . . .
H22 H 0.5529 0.1792 0.9827 0.037 Uiso 1 1 calc R . .
C23 C 0.64720(16) 0.06051(15) 0.94422(9) 0.0342(4) Uani 1 1 d . . .
H23 H 0.6164 -0.0282 0.9497 0.041 Uiso 1 1 calc R . .
C24 C 0.73099(16) 0.06685(15) 0.91691(9) 0.0324(3) Uani 1 1 d . . .
H24 H 0.7599 -0.0177 0.9057 0.039 Uiso 1 1 calc R . .
C25 C 0.77207(14) 0.19602(14) 0.90611(8) 0.0276(3) Uani 1 1 d . . .
H25 H 0.8287 0.1990 0.8871 0.033 Uiso 1 1 calc R . .
C26 C 0.73180(13) 0.32272(14) 0.92261(8) 0.0234(3) Uani 1 1 d . . .




_atom_site_aniso_label

_atom_site_aniso_U_11

_atom_site_aniso_U_22

_atom_site_aniso_U_33

_atom_site_aniso_U_23

_atom_site_aniso_U_13

_atom_site_aniso_U_12



























O1 0.0325(5) 0.0271(5) 0.0337(6) -0.0027(4) 0.0224(5) -0.0026(4)
C1 0.0355(8) 0.0336(8) 0.0322(8) 0.0028(6) 0.0226(7) -0.0003(7)
C2 0.0547(10) 0.0349(8) 0.0387(9) 0.0023(7) 0.0356(9) 0.0062(8)
C3 0.0567(11) 0.0260(8) 0.0266(8) -0.0018(6) 0.0240(8) -0.0008(7)
C4 0.0358(8) 0.0308(8) 0.0256(7) -0.0039(6) 0.0131(7) -0.0051(7)
C5 0.0285(7) 0.0300(7) 0.0265(7) -0.0008(6) 0.0149(6) -0.0004(6)
C6 0.0275(7) 0.0222(7) 0.0207(6) 0.0031(5) 0.0131(6) 0.0010(6)
C7 0.0198(6) 0.0238(7) 0.0222(7) 0.0006(5) 0.0102(6) 0.0004(5)
C8 0.0266(7) 0.0248(7) 0.0203(6) -0.0016(5) 0.0141(6) -0.0016(6)
C9 0.0280(7) 0.0296(7) 0.0246(7) -0.0002(6) 0.0152(6) 0.0002(6)
C10 0.0425(9) 0.0284(8) 0.0302(8) 0.0062(6) 0.0213(7) 0.0060(7)
C11 0.0518(10) 0.0248(7) 0.0376(8) -0.0002(7) 0.0311(8) -0.0051(7)
C12 0.0349(8) 0.0348(8) 0.0384(9) -0.0052(7) 0.0233(7) -0.0105(7)
C13 0.0275(7) 0.0308(8) 0.0293(7) 0.0018(6) 0.0149(7) -0.0014(6)
C14 0.0193(6) 0.0218(7) 0.0226(7) 0.0006(5) 0.0104(6) 0.0000(5)
C15 0.0227(7) 0.0219(7) 0.0191(6) 0.0035(5) 0.0092(6) 0.0036(5)
C16 0.0262(7) 0.0270(7) 0.0257(7) 0.0008(6) 0.0127(6) 0.0003(6)
C17 0.0340(8) 0.0259(7) 0.0309(8) -0.0050(6) 0.0145(7) -0.0028(6)
C18 0.0412(9) 0.0286(8) 0.0307(8) -0.0050(6) 0.0199(7) 0.0038(7)
C19 0.0337(8) 0.0312(8) 0.0279(7) 0.0021(6) 0.0185(7) 0.0044(6)
C20 0.0257(7) 0.0239(7) 0.0220(7) 0.0025(5) 0.0117(6) 0.0019(6)
C21 0.0268(7) 0.0246(7) 0.0210(7) 0.0001(6) 0.0119(6) 0.0000(6)
C22 0.0346(8) 0.0319(8) 0.0263(7) -0.0002(6) 0.0184(7) -0.0057(6)
C23 0.0442(9) 0.0254(7) 0.0296(8) 0.0000(6) 0.0196(7) -0.0081(7)
C24 0.0405(8) 0.0245(7) 0.0296(8) -0.0010(6) 0.0190(7) -0.0001(6)
C25 0.0301(7) 0.0264(7) 0.0237(7) 0.0004(6) 0.0143(6) 0.0007(6)
C26 0.0214(6) 0.0248(7) 0.0183(6) 0.0005(5) 0.0083(6) -0.0011(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.

;




_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 C21 1.3882(16) . ?
O1 C20 1.3893(16) . ?
C1 C2 1.390(2) . ?
C1 C6 1.394(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3932(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.4943(18) . ?
C7 C14 1.3584(18) . ?
C7 C8 1.5001(18) . ?
C8 C13 1.3925(19) . ?
C8 C9 1.3948(19) . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.4895(18) . ?
C14 C26 1.4912(18) . ?
C15 C20 1.3971(19) . ?
C15 C16 1.4045(19) . ?
C16 C17 1.384(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.3904(19) . ?
C19 H19 0.9500 . ?
C21 C22 1.3879(19) . ?
C21 C26 1.3943(19) . ?
C22 C23 1.379(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.393(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.3822(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.4025(19) . ?
C25 H25 0.9500 . ?




_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















































































C21 O1 C20 115.41(10) . . ?
C2 C1 C6 120.01(14) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C3 C2 C1 120.67(14) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.65(14) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.06(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.02(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.52(13) . . ?
C5 C6 C7 119.69(12) . . ?
C1 C6 C7 121.76(12) . . ?
C14 C7 C6 121.79(12) . . ?
C14 C7 C8 125.17(12) . . ?
C6 C7 C8 112.67(11) . . ?
C13 C8 C9 118.52(13) . . ?
C13 C8 C7 122.50(12) . . ?
C9 C8 C7 118.86(12) . . ?
C10 C9 C8 120.81(13) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.94(14) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 119.76(14) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.48(14) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.44(14) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C7 C14 C15 125.93(12) . . ?
C7 C14 C26 122.51(12) . . ?
C15 C14 C26 111.30(11) . . ?
C20 C15 C16 116.04(12) . . ?
C20 C15 C14 117.31(12) . . ?
C16 C15 C14 126.65(12) . . ?
C17 C16 C15 121.55(14) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 120.57(14) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.62(13) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 119.04(14) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
O1 C20 C19 115.46(12) . . ?
O1 C20 C15 121.42(12) . . ?
C19 C20 C15 123.11(13) . . ?
C22 C21 O1 116.59(12) . . ?
C22 C21 C26 122.64(13) . . ?
O1 C21 C26 120.76(12) . . ?
C23 C22 C21 119.05(13) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 120.03(13) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.08(14) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 121.36(13) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C21 C26 C25 116.70(12) . . ?
C21 C26 C14 118.03(12) . . ?
C25 C26 C14 125.26(12) . . ?



_diffrn_measured_fraction_theta_max 0.986

_diffrn_reflns_theta_full        27.62

_diffrn_measured_fraction_theta_full 0.986

_refine_diff_density_max         0.202

_refine_diff_density_min         -0.282

_refine_diff_density_rms         0.051


data_120220b_0m
_database_code_depnum_ccdc_archive 'CCDC 893967'
#TrackingRef '120220b_0m.cif'




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C26 H16 O2'

_chemical_formula_weight         360.39




_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   C2/c




_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'
'-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                   14.685(4)

_cell_length_b                   12.803(4)

_cell_length_c                   9.354(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 95.080(5)

_cell_angle_gamma                90.00

_cell_volume                     1751.7(9)

_cell_formula_units_Z            4

_cell_measurement_temperature    150(2)

_cell_measurement_reflns_used    1606

_cell_measurement_theta_min      2.95

_cell_measurement_theta_max      29.40



_exptl_crystal_description       ?

_exptl_crystal_colour            ?

_exptl_crystal_size_max          0.31

_exptl_crystal_size_mid          0.26

_exptl_crystal_size_min          0.25

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.367

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             752

_exptl_absorpt_coefficient_mu    0.085

_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_correction_T_min  0.9740

_exptl_absorpt_correction_T_max  0.9790

_exptl_absorpt_process_details   SADABS



_exptl_special_details           
;

?

;



_diffrn_ambient_temperature      150(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            4402

_diffrn_reflns_av_R_equivalents  0.0275

_diffrn_reflns_av_sigmaI/netI    0.0319

_diffrn_reflns_limit_h_min       -16

_diffrn_reflns_limit_h_max       17

_diffrn_reflns_limit_k_min       -15

_diffrn_reflns_limit_k_max       14

_diffrn_reflns_limit_l_min       -9

_diffrn_reflns_limit_l_max       11

_diffrn_reflns_theta_min         2.11

_diffrn_reflns_theta_max         25.24

_reflns_number_total             1586

_reflns_number_gt                1336

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F^2^, conventional R-factors R are based

on F, with F set to zero for negative F^2^. The threshold expression of

F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F^2^ are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.8360P] 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     SHELXL

_refine_ls_extinction_coef       0.0050(7)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^

_refine_ls_number_reflns         1586

_refine_ls_number_parameters     128

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0414

_refine_ls_R_factor_gt           0.0350

_refine_ls_wR_factor_ref         0.0915

_refine_ls_wR_factor_gt          0.0871

_refine_ls_goodness_of_fit_ref   1.061

_refine_ls_restrained_S_all      1.061

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000




_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 0.05182(9) 0.72800(10) 0.04176(14) 0.0207(3) Uani 1 1 d . . .
C2 C 0.02807(10) 0.83272(11) 0.04461(15) 0.0252(3) Uani 1 1 d . . .
H2 H 0.0730 0.8854 0.0377 0.030 Uiso 1 1 calc R . .
C3 C -0.06193(10) 0.85908(11) 0.05761(15) 0.0283(4) Uani 1 1 d . . .
H3 H -0.0795 0.9305 0.0586 0.034 Uiso 1 1 calc R . .
C4 C -0.12707(10) 0.78132(11) 0.06925(15) 0.0256(4) Uani 1 1 d . . .
H4 H -0.1886 0.7998 0.0814 0.031 Uiso 1 1 calc R . .
C5 C -0.10257(9) 0.67745(11) 0.06317(14) 0.0216(3) Uani 1 1 d . . .
H5 H -0.1475 0.6249 0.0714 0.026 Uiso 1 1 calc R . .
C6 C -0.01236(9) 0.64834(10) 0.04508(13) 0.0191(3) Uani 1 1 d . . .
C7 C 0.02179(9) 0.53932(10) 0.03774(14) 0.0181(3) Uani 1 1 d . . .
C8 C 0.11290(9) 0.53047(10) 0.11920(14) 0.0190(3) Uani 1 1 d . . .
C9 C 0.14297(9) 0.44689(10) 0.20769(14) 0.0210(3) Uani 1 1 d . . .
H9 H 0.1026 0.3906 0.2217 0.025 Uiso 1 1 calc R . .
C10 C 0.23073(10) 0.44515(11) 0.27495(14) 0.0237(3) Uani 1 1 d . . .
H10 H 0.2505 0.3874 0.3334 0.028 Uiso 1 1 calc R . .
C11 C 0.28992(10) 0.52784(11) 0.25702(15) 0.0260(4) Uani 1 1 d . . .
H11 H 0.3509 0.5251 0.3001 0.031 Uiso 1 1 calc R . .
C12 C 0.26054(9) 0.61412(12) 0.17678(15) 0.0241(3) Uani 1 1 d . . .
H12 H 0.3002 0.6717 0.1665 0.029 Uiso 1 1 calc R . .
C13 C 0.17229(9) 0.61489(10) 0.11193(14) 0.0201(3) Uani 1 1 d . . .
O1 O 0.14399(6) 0.70528(7) 0.03827(10) 0.0243(3) Uani 1 1 d . . .




_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 0.0211(7) 0.0204(7) 0.0204(7) 0.0014(5) 0.0008(5) 0.0006(6)
C2 0.0303(8) 0.0171(7) 0.0275(8) 0.0005(6) -0.0022(6) -0.0025(6)
C3 0.0366(9) 0.0187(7) 0.0285(8) -0.0014(6) -0.0032(7) 0.0072(6)
C4 0.0257(8) 0.0260(8) 0.0246(8) -0.0033(6) -0.0010(6) 0.0069(6)
C5 0.0219(7) 0.0229(8) 0.0198(7) -0.0014(5) 0.0014(6) 0.0006(6)
C6 0.0224(7) 0.0182(7) 0.0167(7) 0.0009(5) 0.0006(5) 0.0002(5)
C7 0.0182(7) 0.0179(7) 0.0188(6) 0.0024(5) 0.0047(5) 0.0007(5)
C8 0.0198(7) 0.0190(7) 0.0187(7) -0.0033(5) 0.0042(5) 0.0009(5)
C9 0.0244(7) 0.0184(7) 0.0205(7) -0.0018(5) 0.0042(6) 0.0013(6)
C10 0.0267(8) 0.0240(8) 0.0204(7) -0.0008(6) 0.0014(6) 0.0056(6)
C11 0.0204(7) 0.0323(8) 0.0247(8) -0.0043(6) -0.0005(6) 0.0043(6)
C12 0.0208(7) 0.0259(8) 0.0260(8) -0.0031(6) 0.0042(6) -0.0024(6)
C13 0.0221(7) 0.0188(7) 0.0198(7) 0.0004(5) 0.0046(5) 0.0025(6)
O1 0.0210(5) 0.0199(5) 0.0320(6) 0.0053(4) 0.0030(4) -0.0005(4)



_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell esds are taken

into account individually in the estimation of esds in distances, angles

and torsion angles; correlations between esds in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell esds is used for estimating esds involving l.s. planes.

;




_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 C2 1.3862(19) . ?
C1 O1 1.3877(17) . ?
C1 C6 1.3909(19) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4007(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.4868(19) . ?
C7 C7 1.357(3) 5_565 ?
C7 C8 1.4842(19) . ?
C8 C13 1.3942(19) . ?
C8 C9 1.4002(19) . ?
C9 C10 1.3834(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3815(19) . ?
C12 H12 0.9500 . ?
C13 O1 1.3915(16) . ?




_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 O1 116.79(12) . . ?
C2 C1 C6 122.46(13) . . ?
O1 C1 C6 120.74(12) . . ?
C3 C2 C1 118.87(13) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.15(13) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.18(14) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.94(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.23(12) . . ?
C1 C6 C7 117.08(12) . . ?
C5 C6 C7 125.59(12) . . ?
C7 C7 C8 124.94(15) 5_565 . ?
C7 C7 C6 125.10(15) 5_565 . ?
C8 C7 C6 109.90(11) . . ?
C13 C8 C9 117.09(12) . . ?
C13 C8 C7 117.07(12) . . ?
C9 C8 C7 125.77(12) . . ?
C10 C9 C8 120.89(13) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.03(13) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.38(13) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 118.65(13) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 O1 116.79(12) . . ?
C12 C13 C8 122.66(13) . . ?
O1 C13 C8 120.55(12) . . ?
C1 O1 C13 114.32(10) . . ?



_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        25.24

_diffrn_measured_fraction_theta_full 0.998

_refine_diff_density_max         0.204

_refine_diff_density_min         -0.167

_refine_diff_density_rms         0.037