# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'King Kuok Hii'
_publ_contact_author_email       MIMI.HII@IMPERIAL.AC.UK

_publ_section_title              
;
Unusual Regiodivergence in Metal-Catalysed Intramolecular
Cyclisation of ?-Allenols
;
loop_
_publ_author_name
'King Kuok Hii.'
'Jannine L. Arbour'
'Henry S. Rzepa'
'Andrew J P White'

# Attachment 'Crystalstructures.cif'

data_Compound_4
_database_code_depnum_ccdc_archive 'CCDC 726110'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 O'
_chemical_formula_sum            'C18 H18 O'
_chemical_formula_weight         250.32

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           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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                   14.1920(13)
_cell_length_b                   12.8979(13)
_cell_length_c                   7.4178(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1357.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1182
_cell_measurement_theta_min      3.9553
_cell_measurement_theta_max      27.4349

_exptl_crystal_description       'platy needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 15.9863
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5103
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_sigmaI/netI    0.1464
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2203
_reflns_number_gt                1140
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_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.

Results of chirality/polarity tests
_refine_ls_R_factor_obs+ 0.0497
_refine_ls_wR_factor_obs+ 0.0803
_refine_ls_abs_structure_Flack+ 0(3)
_refine_ls_R_factor_obs- 0.0497
_refine_ls_wR_factor_obs- 0.0803
_refine_ls_abs_structure_Flack- 1(3)
;

_chemical_absolute_configuration .
_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^)+(0.0309P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881, 743 Friedel pairs'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         2203
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_restrained_S_all      0.853
_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 0.0976(3) 0.2916(3) 0.9947(5) 0.0397(11) Uani 1 1 d . . .
O2 O 0.07311(16) 0.25519(19) 0.8138(3) 0.0416(7) Uani 1 1 d . . .
C3 C 0.1424(2) 0.2821(3) 0.6812(5) 0.0323(10) Uani 1 1 d . . .
H3A H 0.1110 0.3173 0.5788 0.039 Uiso 1 1 calc R . .
H3B H 0.1722 0.2181 0.6348 0.039 Uiso 1 1 calc R . .
C4 C 0.2193(3) 0.3541(3) 0.7591(4) 0.0309(9) Uani 1 1 d . . .
C5 C 0.1707(2) 0.4422(3) 0.8588(4) 0.0268(9) Uani 1 1 d . . .
C6 C 0.1882(2) 0.5460(3) 0.8403(5) 0.0322(9) Uani 1 1 d . . .
H6A H 0.2320 0.5696 0.7527 0.039 Uiso 1 1 calc R . .
C7 C 0.1416(2) 0.6168(3) 0.9504(5) 0.0352(9) Uani 1 1 d . . .
H7A H 0.1534 0.6890 0.9375 0.042 Uiso 1 1 calc R . .
C8 C 0.0780(2) 0.5821(3) 1.0787(6) 0.0377(10) Uani 1 1 d . . .
H8A H 0.0467 0.6307 1.1542 0.045 Uiso 1 1 calc R . .
C9 C 0.0599(2) 0.4783(3) 1.0975(5) 0.0392(10) Uani 1 1 d . . .
H9A H 0.0157 0.4553 1.1849 0.047 Uiso 1 1 calc R . .
C10 C 0.1061(3) 0.4065(3) 0.9891(5) 0.0308(10) Uani 1 1 d . . .
C11 C 0.0222(3) 0.2493(3) 1.1170(5) 0.0559(12) Uani 1 1 d . . .
H11A H -0.0387 0.2801 1.0850 0.084 Uiso 1 1 calc R . .
H11B H 0.0375 0.2664 1.2424 0.084 Uiso 1 1 calc R . .
H11C H 0.0187 0.1738 1.1033 0.084 Uiso 1 1 calc R . .
C12 C 0.1955(3) 0.2460(3) 1.0379(5) 0.0433(11) Uani 1 1 d . . .
H12A H 0.1934 0.1695 1.0286 0.052 Uiso 1 1 calc R . .
H12B H 0.2137 0.2644 1.1628 0.052 Uiso 1 1 calc R . .
C13 C 0.2689(3) 0.2895(3) 0.9044(4) 0.0388(10) Uani 1 1 d . . .
H13A H 0.3149 0.3333 0.9699 0.047 Uiso 1 1 calc R . .
H13B H 0.3036 0.2316 0.8472 0.047 Uiso 1 1 calc R . .
C14 C 0.2830(2) 0.3921(3) 0.6083(5) 0.0279(9) Uani 1 1 d . . .
C15 C 0.3804(3) 0.3811(3) 0.6147(5) 0.0388(10) Uani 1 1 d . . .
H15A H 0.4089 0.3482 0.7154 0.047 Uiso 1 1 calc R . .
C16 C 0.4357(3) 0.4176(3) 0.4759(7) 0.0520(12) Uani 1 1 d . . .
H16A H 0.5022 0.4097 0.4820 0.062 Uiso 1 1 calc R . .
C17 C 0.3961(3) 0.4652(3) 0.3295(7) 0.0566(13) Uani 1 1 d . . .
H17A H 0.4351 0.4908 0.2354 0.068 Uiso 1 1 calc R . .
C18 C 0.3000(3) 0.4758(3) 0.3185(6) 0.0470(11) Uani 1 1 d . . .
H18A H 0.2720 0.5072 0.2158 0.056 Uiso 1 1 calc R . .
C19 C 0.2444(3) 0.4403(3) 0.4587(5) 0.0398(10) Uani 1 1 d . . .
H19A H 0.1780 0.4492 0.4522 0.048 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.053(3) 0.040(3) 0.027(2) -0.0092(19) 0.001(2) -0.010(2)
O2 0.0489(16) 0.0425(15) 0.0333(14) -0.0042(14) -0.0011(16) -0.0147(14)
C3 0.039(2) 0.024(2) 0.033(2) -0.0014(18) -0.003(2) -0.0006(19)
C4 0.034(2) 0.031(2) 0.0277(19) -0.0045(17) -0.0057(19) 0.000(2)
C5 0.023(2) 0.032(2) 0.026(2) -0.0046(17) -0.0047(18) -0.0007(18)
C6 0.032(2) 0.029(2) 0.036(2) 0.004(2) 0.0043(19) -0.0018(19)
C7 0.040(2) 0.024(2) 0.042(2) -0.006(2) -0.005(2) 0.000(2)
C8 0.033(2) 0.044(3) 0.036(2) -0.018(2) -0.005(2) 0.006(2)
C9 0.031(2) 0.055(3) 0.031(2) -0.006(2) 0.005(2) -0.001(2)
C10 0.030(2) 0.032(3) 0.031(2) 0.0009(19) -0.0056(19) -0.0052(19)
C11 0.071(3) 0.055(3) 0.041(2) 0.004(3) 0.007(2) -0.021(2)
C12 0.065(3) 0.035(2) 0.030(2) 0.0039(18) -0.010(2) 0.004(2)
C13 0.047(3) 0.034(2) 0.035(2) -0.0061(18) -0.008(2) 0.007(2)
C14 0.031(2) 0.024(2) 0.029(2) -0.0075(18) 0.008(2) 0.0023(18)
C15 0.036(3) 0.042(3) 0.039(2) -0.020(2) 0.002(2) -0.004(2)
C16 0.041(3) 0.059(3) 0.056(3) -0.023(3) 0.013(3) -0.011(2)
C17 0.057(3) 0.065(3) 0.048(3) -0.022(3) 0.026(3) -0.019(3)
C18 0.062(3) 0.048(3) 0.031(2) -0.006(2) 0.009(2) -0.010(2)
C19 0.039(2) 0.047(2) 0.034(2) -0.006(2) 0.009(2) -0.001(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.464(4) . ?
C1 C10 1.487(5) . ?
C1 C11 1.505(5) . ?
C1 C12 1.543(5) . ?
O2 C3 1.433(4) . ?
C3 C4 1.546(4) . ?
C4 C14 1.519(4) . ?
C4 C5 1.521(4) . ?
C4 C13 1.534(4) . ?
C5 C6 1.369(4) . ?
C5 C10 1.410(4) . ?
C6 C7 1.393(4) . ?
C7 C8 1.386(5) . ?
C8 C9 1.370(5) . ?
C9 C10 1.391(5) . ?
C12 C13 1.543(4) . ?
C14 C19 1.385(5) . ?
C14 C15 1.390(5) . ?
C15 C16 1.378(5) . ?
C16 C17 1.369(6) . ?
C17 C18 1.374(5) . ?
C18 C19 1.384(5) . ?

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 C10 108.2(3) . . ?
O2 C1 C11 105.5(3) . . ?
C10 C1 C11 115.8(3) . . ?
O2 C1 C12 106.4(3) . . ?
C10 C1 C12 108.2(3) . . ?
C11 C1 C12 112.2(3) . . ?
C3 O2 C1 112.9(2) . . ?
O2 C3 C4 112.0(3) . . ?
C14 C4 C5 112.8(3) . . ?
C14 C4 C13 114.8(3) . . ?
C5 C4 C13 105.8(3) . . ?
C14 C4 C3 109.8(3) . . ?
C5 C4 C3 108.0(3) . . ?
C13 C4 C3 105.1(3) . . ?
C6 C5 C10 120.4(3) . . ?
C6 C5 C4 126.8(3) . . ?
C10 C5 C4 112.6(3) . . ?
C5 C6 C7 119.8(3) . . ?
C8 C7 C6 120.0(3) . . ?
C9 C8 C7 120.5(3) . . ?
C8 C9 C10 120.3(4) . . ?
C9 C10 C5 119.0(3) . . ?
C9 C10 C1 127.6(4) . . ?
C5 C10 C1 113.4(3) . . ?
C1 C12 C13 109.7(3) . . ?
C4 C13 C12 109.8(3) . . ?
C19 C14 C15 117.8(3) . . ?
C19 C14 C4 120.0(3) . . ?
C15 C14 C4 122.2(3) . . ?
C16 C15 C14 120.4(4) . . ?
C17 C16 C15 120.8(4) . . ?
C16 C17 C18 120.0(4) . . ?
C17 C18 C19 119.3(5) . . ?
C18 C19 C14 121.7(4) . . ?

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
C10 C1 O2 C3 59.9(4) . . . . ?
C11 C1 O2 C3 -175.4(3) . . . . ?
C12 C1 O2 C3 -56.1(4) . . . . ?
C1 O2 C3 C4 -6.9(4) . . . . ?
O2 C3 C4 C14 -172.3(3) . . . . ?
O2 C3 C4 C5 -48.9(3) . . . . ?
O2 C3 C4 C13 63.7(3) . . . . ?
C14 C4 C5 C6 -8.8(5) . . . . ?
C13 C4 C5 C6 117.5(4) . . . . ?
C3 C4 C5 C6 -130.4(3) . . . . ?
C14 C4 C5 C10 175.3(3) . . . . ?
C13 C4 C5 C10 -58.4(4) . . . . ?
C3 C4 C5 C10 53.8(4) . . . . ?
C10 C5 C6 C7 -0.3(5) . . . . ?
C4 C5 C6 C7 -175.9(3) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C6 C7 C8 C9 -0.5(5) . . . . ?
C7 C8 C9 C10 0.7(6) . . . . ?
C8 C9 C10 C5 -0.7(5) . . . . ?
C8 C9 C10 C1 177.9(4) . . . . ?
C6 C5 C10 C9 0.5(5) . . . . ?
C4 C5 C10 C9 176.7(3) . . . . ?
C6 C5 C10 C1 -178.3(3) . . . . ?
C4 C5 C10 C1 -2.1(4) . . . . ?
O2 C1 C10 C9 125.9(4) . . . . ?
C11 C1 C10 C9 7.6(6) . . . . ?
C12 C1 C10 C9 -119.2(4) . . . . ?
O2 C1 C10 C5 -55.5(4) . . . . ?
C11 C1 C10 C5 -173.7(3) . . . . ?
C12 C1 C10 C5 59.4(4) . . . . ?
O2 C1 C12 C13 63.2(4) . . . . ?
C10 C1 C12 C13 -52.9(4) . . . . ?
C11 C1 C12 C13 178.1(3) . . . . ?
C14 C4 C13 C12 -174.0(3) . . . . ?
C5 C4 C13 C12 60.9(4) . . . . ?
C3 C4 C13 C12 -53.2(3) . . . . ?
C1 C12 C13 C4 -6.3(4) . . . . ?
C5 C4 C14 C19 -66.4(4) . . . . ?
C13 C4 C14 C19 172.2(3) . . . . ?
C3 C4 C14 C19 54.1(4) . . . . ?
C5 C4 C14 C15 113.0(3) . . . . ?
C13 C4 C14 C15 -8.4(5) . . . . ?
C3 C4 C14 C15 -126.5(3) . . . . ?
C19 C14 C15 C16 0.1(5) . . . . ?
C4 C14 C15 C16 -179.3(3) . . . . ?
C14 C15 C16 C17 -0.1(6) . . . . ?
C15 C16 C17 C18 -0.8(6) . . . . ?
C16 C17 C18 C19 1.6(6) . . . . ?
C17 C18 C19 C14 -1.5(6) . . . . ?
C15 C14 C19 C18 0.6(6) . . . . ?
C4 C14 C19 C18 -179.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.867
_diffrn_reflns_theta_full        22.50
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037

#===END

data_Compound_5
_database_code_depnum_ccdc_archive 'CCDC 726111'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H36 O2'
_chemical_formula_sum            'C36 H36 O2'
_chemical_formula_weight         500.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.3771(3)
_cell_length_b                   19.8345(8)
_cell_length_c                   23.2868(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.321(4)
_cell_angle_gamma                90.00
_cell_volume                     2921.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2558
_cell_measurement_theta_min      1.9119
_cell_measurement_theta_max      63.0419

_exptl_crystal_description       needles
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 8.2556
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8043
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         63.18
_reflns_number_total             4532
_reflns_number_gt                2460
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_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^)+(0.0799P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4532
_refine_ls_number_parameters     357
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_restrained_S_all      0.845
_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 0.9102(2) 0.37446(7) 0.42395(6) 0.0626(4) Uani 1 1 d . . .
C2 C 0.7060(3) 0.40325(11) 0.42493(9) 0.0583(5) Uani 1 1 d . . .
C3 C 0.5983(3) 0.37233(11) 0.47274(9) 0.0628(6) Uani 1 1 d . . .
H3A H 0.6735 0.3855 0.5099 0.075 Uiso 1 1 calc R . .
H3B H 0.4553 0.3896 0.4705 0.075 Uiso 1 1 calc R . .
C4 C 0.5912(3) 0.29638(11) 0.46887(10) 0.0605(6) Uani 1 1 d . . .
H4A H 0.5063 0.2830 0.4331 0.073 Uiso 1 1 calc R . .
H4B H 0.5255 0.2784 0.5009 0.073 Uiso 1 1 calc R . .
C5 C 0.8158(3) 0.26729(10) 0.47053(9) 0.0540(5) Uani 1 1 d . . .
C6 C 0.9115(3) 0.30254(11) 0.42101(9) 0.0604(6) Uani 1 1 d . . .
H6A H 1.0563 0.2874 0.4214 0.072 Uiso 1 1 calc R . .
H6B H 0.8334 0.2886 0.3844 0.072 Uiso 1 1 calc R . .
O7 O 0.5710(2) 0.38748(7) 0.37332(6) 0.0588(4) Uani 1 1 d . . .
C8 C 0.6407(3) 0.40680(11) 0.32034(8) 0.0601(6) Uani 1 1 d . . .
H8A H 0.7785 0.3874 0.3172 0.072 Uiso 1 1 calc R . .
H8B H 0.6518 0.4555 0.3183 0.072 Uiso 1 1 calc R . .
C9 C 0.4773(3) 0.38067(10) 0.27121(9) 0.0541(5) Uani 1 1 d D A .
C10 C 0.2627(3) 0.41465(10) 0.27578(10) 0.0642(6) Uani 1 1 d D . .
H10A H 0.1573 0.3955 0.2466 0.077 Uiso 0.801(13) 1 calc PR A 1
H10B H 0.2204 0.4044 0.3134 0.077 Uiso 0.801(13) 1 calc PR A 1
H10C H 0.2338 0.4117 0.3165 0.077 Uiso 0.199(13) 1 d PR A 2
H10D H 0.1517 0.3881 0.2521 0.077 Uiso 0.199(13) 1 d PR A 2
C11 C 0.2653(14) 0.4894(2) 0.2682(4) 0.0759(19) Uani 0.801(13) 1 d PDU A 1
H11A H 0.2990 0.5062 0.2333 0.091 Uiso 0.801(13) 1 calc PR A 1
C12 C 0.2243(10) 0.53206(19) 0.3066(3) 0.0871(15) Uani 0.801(13) 1 d PDU A 1
C13 C 0.1806(16) 0.5753(2) 0.3449(4) 0.145(4) Uani 0.801(13) 1 d PDU A 1
H13A H 0.1468 0.5596 0.3816 0.174 Uiso 0.801(13) 1 d PR A 1
H13B H 0.1843 0.6228 0.3372 0.174 Uiso 0.801(13) 1 d PR A 1
C11' C 0.244(7) 0.4870(10) 0.2582(15) 0.086(8) Uiso 0.199(13) 1 d PDU A 2
H11B H 0.3006 0.4999 0.2250 0.103 Uiso 0.199(13) 1 calc PR A 2
C12' C 0.157(3) 0.5322(7) 0.2861(8) 0.069(5) Uiso 0.199(13) 1 d PDU A 2
C13' C 0.045(4) 0.5726(11) 0.3160(10) 0.122(7) Uiso 0.199(13) 1 d PDU A 2
H13C H -0.0123 0.5557 0.3493 0.146 Uiso 0.199(13) 1 d PR A 2
H13D H 0.0300 0.6194 0.3059 0.146 Uiso 0.199(13) 1 d PR A 2
C14 C 0.5454(3) 0.39754(11) 0.21218(9) 0.0586(6) Uani 1 1 d . . .
C15 C 0.7175(4) 0.43721(13) 0.20478(10) 0.0730(7) Uani 1 1 d . A .
H15A H 0.7984 0.4554 0.2371 0.088 Uiso 1 1 calc R . .
C16 C 0.7723(4) 0.45057(15) 0.15075(13) 0.0918(8) Uani 1 1 d . . .
H16A H 0.8905 0.4769 0.1472 0.110 Uiso 1 1 calc R A .
C17 C 0.6556(6) 0.42563(16) 0.10250(12) 0.0970(9) Uani 1 1 d . A .
H17A H 0.6939 0.4347 0.0660 0.116 Uiso 1 1 calc R . .
C18 C 0.4814(5) 0.38714(14) 0.10804(12) 0.0932(9) Uani 1 1 d . . .
H18A H 0.3999 0.3701 0.0753 0.112 Uiso 1 1 calc R A .
C19 C 0.4263(4) 0.37354(12) 0.16266(11) 0.0761(7) Uani 1 1 d . A .
H19A H 0.3067 0.3477 0.1660 0.091 Uiso 1 1 calc R . .
C20 C 0.4622(3) 0.30432(11) 0.27806(9) 0.0593(6) Uani 1 1 d . . .
C21 C 0.2954(4) 0.27192(12) 0.29937(10) 0.0720(6) Uani 1 1 d . A .
H21A H 0.1839 0.2975 0.3098 0.086 Uiso 1 1 calc R . .
C22 C 0.2905(5) 0.20236(14) 0.30549(12) 0.0916(8) Uani 1 1 d . . .
H22A H 0.1755 0.1820 0.3193 0.110 Uiso 1 1 calc R A .
C23 C 0.4537(7) 0.16369(16) 0.29143(13) 0.1059(10) Uani 1 1 d . A .
H23A H 0.4506 0.1171 0.2958 0.127 Uiso 1 1 calc R . .
C24 C 0.6218(6) 0.19401(16) 0.27091(13) 0.0991(9) Uani 1 1 d . . .
H24A H 0.7336 0.1680 0.2613 0.119 Uiso 1 1 calc R A .
C25 C 0.6260(4) 0.26323(13) 0.26435(10) 0.0775(7) Uani 1 1 d . A .
H25A H 0.7417 0.2830 0.2504 0.093 Uiso 1 1 calc R . .
C26 C 0.7425(4) 0.47815(12) 0.43274(10) 0.0834(8) Uani 1 1 d . . .
H26A H 0.8106 0.4952 0.4013 0.125 Uiso 1 1 calc R . .
H26B H 0.8309 0.4862 0.4686 0.125 Uiso 1 1 calc R . .
H26C H 0.6094 0.5005 0.4333 0.125 Uiso 1 1 calc R . .
C27 C 0.8190(3) 0.19193(11) 0.45814(9) 0.0594(6) Uani 1 1 d . . .
C28 C 0.6412(4) 0.15408(13) 0.44087(11) 0.0772(7) Uani 1 1 d . . .
H28A H 0.5093 0.1748 0.4367 0.093 Uiso 1 1 calc R . .
C29 C 0.6547(5) 0.08584(14) 0.42950(11) 0.0917(8) Uani 1 1 d . . .
H29A H 0.5320 0.0616 0.4175 0.110 Uiso 1 1 calc R . .
C30 C 0.8452(6) 0.05362(15) 0.43557(12) 0.0964(9) Uani 1 1 d . . .
H30A H 0.8533 0.0077 0.4279 0.116 Uiso 1 1 calc R . .
C31 C 1.0222(5) 0.08971(15) 0.45300(14) 0.1099(10) Uani 1 1 d . . .
H31A H 1.1532 0.0684 0.4577 0.132 Uiso 1 1 calc R . .
C32 C 1.0095(4) 0.15798(14) 0.46387(12) 0.0920(8) Uani 1 1 d . . .
H32A H 1.1333 0.1818 0.4754 0.110 Uiso 1 1 calc R . .
C33 C 0.9410(3) 0.27974(10) 0.53021(9) 0.0544(5) Uani 1 1 d . . .
C34 C 0.8770(4) 0.24868(12) 0.57828(10) 0.0732(7) Uani 1 1 d . . .
H34A H 0.7538 0.2231 0.5739 0.088 Uiso 1 1 calc R . .
C35 C 0.9910(5) 0.25471(14) 0.63229(11) 0.0891(8) Uani 1 1 d . . .
H35A H 0.9437 0.2335 0.6639 0.107 Uiso 1 1 calc R . .
C36 C 1.1733(5) 0.29168(15) 0.63983(12) 0.0894(8) Uani 1 1 d . . .
H36A H 1.2524 0.2948 0.6761 0.107 Uiso 1 1 calc R . .
C37 C 1.2375(4) 0.32380(14) 0.59346(12) 0.0852(8) Uani 1 1 d . . .
H37A H 1.3601 0.3496 0.5982 0.102 Uiso 1 1 calc R . .
C38 C 1.1215(3) 0.31824(12) 0.53935(10) 0.0696(7) Uani 1 1 d . . .
H38A H 1.1667 0.3411 0.5083 0.084 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0543(9) 0.0732(11) 0.0606(10) 0.0094(7) 0.0087(7) -0.0059(7)
C2 0.0579(13) 0.0635(14) 0.0524(13) 0.0005(11) 0.0034(10) -0.0027(11)
C3 0.0625(14) 0.0694(15) 0.0587(14) 0.0015(11) 0.0169(11) 0.0044(11)
C4 0.0519(13) 0.0689(15) 0.0629(14) 0.0061(11) 0.0160(10) 0.0021(11)
C5 0.0501(12) 0.0628(14) 0.0509(13) 0.0032(10) 0.0132(10) 0.0015(10)
C6 0.0543(13) 0.0769(16) 0.0521(13) 0.0037(11) 0.0150(10) 0.0030(11)
O7 0.0570(8) 0.0676(10) 0.0520(9) 0.0023(7) 0.0080(7) -0.0060(7)
C8 0.0540(12) 0.0713(15) 0.0556(14) 0.0030(11) 0.0087(10) -0.0032(11)
C9 0.0477(12) 0.0584(14) 0.0556(13) 0.0010(10) 0.0035(10) 0.0035(9)
C10 0.0532(12) 0.0584(14) 0.0799(16) 0.0022(12) 0.0047(11) 0.0057(10)
C11 0.073(3) 0.064(3) 0.093(4) 0.005(2) 0.021(3) 0.0126(19)
C12 0.087(3) 0.061(2) 0.115(4) 0.003(2) 0.023(3) 0.008(2)
C13 0.228(8) 0.060(3) 0.166(6) 0.001(3) 0.099(6) 0.007(3)
C14 0.0595(13) 0.0600(13) 0.0552(14) 0.0039(11) 0.0028(11) 0.0092(11)
C15 0.0652(14) 0.0960(19) 0.0585(15) 0.0096(13) 0.0100(12) 0.0011(13)
C16 0.0908(19) 0.113(2) 0.0749(19) 0.0236(17) 0.0248(16) 0.0068(16)
C17 0.137(3) 0.092(2) 0.065(2) 0.0175(16) 0.0284(18) 0.027(2)
C18 0.136(3) 0.0801(19) 0.0592(18) -0.0011(14) -0.0035(17) 0.0116(18)
C19 0.0930(18) 0.0710(16) 0.0625(16) 0.0007(13) 0.0032(13) -0.0001(13)
C20 0.0629(14) 0.0607(14) 0.0529(14) -0.0007(10) 0.0026(11) 0.0062(11)
C21 0.0868(17) 0.0619(16) 0.0677(16) -0.0015(12) 0.0114(13) -0.0031(13)
C22 0.128(2) 0.0687(19) 0.0776(19) 0.0069(14) 0.0108(17) -0.0173(17)
C23 0.170(3) 0.0623(19) 0.079(2) 0.0016(15) -0.006(2) 0.014(2)
C24 0.134(3) 0.076(2) 0.085(2) -0.0081(16) 0.0028(19) 0.0384(19)
C25 0.0838(18) 0.0769(19) 0.0713(17) -0.0029(13) 0.0081(13) 0.0193(14)
C26 0.103(2) 0.0672(17) 0.0780(19) -0.0024(13) 0.0029(14) -0.0106(13)
C27 0.0573(13) 0.0659(15) 0.0562(14) 0.0008(11) 0.0121(10) 0.0033(11)
C28 0.0763(16) 0.0715(17) 0.0828(18) 0.0026(13) 0.0065(13) -0.0026(13)
C29 0.108(2) 0.0711(19) 0.094(2) -0.0041(15) 0.0070(16) -0.0177(17)
C30 0.125(3) 0.0678(18) 0.100(2) -0.0119(15) 0.0261(19) 0.0064(19)
C31 0.102(2) 0.077(2) 0.154(3) -0.0207(19) 0.031(2) 0.0196(18)
C32 0.0752(17) 0.0766(18) 0.126(2) -0.0189(16) 0.0185(16) 0.0071(14)
C33 0.0562(13) 0.0587(13) 0.0501(13) 0.0008(10) 0.0135(10) 0.0068(10)
C34 0.0887(18) 0.0692(16) 0.0648(17) 0.0060(12) 0.0221(13) -0.0018(12)
C35 0.128(2) 0.088(2) 0.0541(17) 0.0135(14) 0.0213(16) 0.0145(18)
C36 0.108(2) 0.092(2) 0.0633(18) -0.0079(15) -0.0076(16) 0.0224(18)
C37 0.0761(17) 0.099(2) 0.0759(19) -0.0051(16) -0.0066(14) 0.0024(14)
C38 0.0594(14) 0.0858(17) 0.0627(15) 0.0024(13) 0.0039(11) 0.0000(12)

_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 C2 1.425(2) . ?
O1 C6 1.428(2) . ?
C2 O7 1.421(2) . ?
C2 C3 1.510(3) . ?
C2 C26 1.511(3) . ?
C3 C4 1.509(3) . ?
C4 C5 1.540(3) . ?
C5 C27 1.523(3) . ?
C5 C33 1.532(3) . ?
C5 C6 1.540(3) . ?
O7 C8 1.416(2) . ?
C8 C9 1.536(3) . ?
C9 C20 1.527(3) . ?
C9 C14 1.531(3) . ?
C9 C10 1.541(3) . ?
C10 C11' 1.492(16) . ?
C10 C11 1.494(5) . ?
C11 C12 1.282(6) . ?
C12 C13 1.292(5) . ?
C11' C12' 1.277(14) . ?
C12' C13' 1.327(14) . ?
C14 C15 1.379(3) . ?
C14 C19 1.382(3) . ?
C15 C16 1.374(3) . ?
C16 C17 1.359(4) . ?
C17 C18 1.368(4) . ?
C18 C19 1.388(3) . ?
C20 C21 1.388(3) . ?
C20 C25 1.394(3) . ?
C21 C22 1.388(3) . ?
C22 C23 1.366(4) . ?
C23 C24 1.367(4) . ?
C24 C25 1.382(4) . ?
C27 C28 1.376(3) . ?
C27 C32 1.381(3) . ?
C28 C29 1.384(3) . ?
C29 C30 1.364(4) . ?
C30 C31 1.355(4) . ?
C31 C32 1.382(4) . ?
C33 C38 1.375(3) . ?
C33 C34 1.384(3) . ?
C34 C35 1.376(3) . ?
C35 C36 1.367(4) . ?
C36 C37 1.361(3) . ?
C37 C38 1.382(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
C2 O1 C6 114.34(15) . . ?
O7 C2 O1 110.76(16) . . ?
O7 C2 C3 104.54(17) . . ?
O1 C2 C3 110.56(16) . . ?
O7 C2 C26 112.68(17) . . ?
O1 C2 C26 105.58(17) . . ?
C3 C2 C26 112.84(19) . . ?
C4 C3 C2 111.97(18) . . ?
C3 C4 C5 110.59(17) . . ?
C27 C5 C33 108.17(16) . . ?
C27 C5 C4 113.46(17) . . ?
C33 C5 C4 109.75(17) . . ?
C27 C5 C6 106.71(16) . . ?
C33 C5 C6 113.31(17) . . ?
C4 C5 C6 105.51(16) . . ?
O1 C6 C5 114.34(17) . . ?
C8 O7 C2 117.00(15) . . ?
O7 C8 C9 107.41(16) . . ?
C20 C9 C14 109.85(17) . . ?
C20 C9 C8 107.61(16) . . ?
C14 C9 C8 110.59(17) . . ?
C20 C9 C10 110.99(17) . . ?
C14 C9 C10 108.83(16) . . ?
C8 C9 C10 108.97(17) . . ?
C11' C10 C9 116.1(14) . . ?
C11 C10 C9 113.8(3) . . ?
C12 C11 C10 124.5(5) . . ?
C11 C12 C13 179.2(7) . . ?
C12' C11' C10 124(2) . . ?
C11' C12' C13' 172(3) . . ?
C15 C14 C19 117.0(2) . . ?
C15 C14 C9 124.0(2) . . ?
C19 C14 C9 119.0(2) . . ?
C16 C15 C14 121.6(2) . . ?
C17 C16 C15 120.7(3) . . ?
C16 C17 C18 119.4(3) . . ?
C17 C18 C19 119.9(3) . . ?
C14 C19 C18 121.4(3) . . ?
C21 C20 C25 116.2(2) . . ?
C21 C20 C9 123.9(2) . . ?
C25 C20 C9 119.8(2) . . ?
C22 C21 C20 121.7(2) . . ?
C23 C22 C21 120.4(3) . . ?
C22 C23 C24 119.5(3) . . ?
C23 C24 C25 120.2(3) . . ?
C24 C25 C20 122.0(3) . . ?
C28 C27 C32 116.4(2) . . ?
C28 C27 C5 124.1(2) . . ?
C32 C27 C5 119.6(2) . . ?
C27 C28 C29 121.4(2) . . ?
C30 C29 C28 121.0(3) . . ?
C31 C30 C29 118.7(3) . . ?
C30 C31 C32 120.4(3) . . ?
C27 C32 C31 122.1(3) . . ?
C38 C33 C34 116.7(2) . . ?
C38 C33 C5 123.99(19) . . ?
C34 C33 C5 119.2(2) . . ?
C35 C34 C33 121.7(3) . . ?
C36 C35 C34 120.4(3) . . ?
C37 C36 C35 119.1(3) . . ?
C36 C37 C38 120.4(3) . . ?
C33 C38 C37 121.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        60.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.037

#===END