# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006

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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_haxu
_database_code_depnum_ccdc_archive 'CCDC 290049'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 O3'
_chemical_formula_weight         324.40

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   C2/c

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'
'-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                   27.321(6)
_cell_length_b                   8.7467(17)
_cell_length_c                   15.029(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.75(3)
_cell_angle_gamma                90.00
_cell_volume                     3558.5(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3491
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      22.97

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9796
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-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_%        1
_diffrn_reflns_number            12624
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3134
_reflns_number_gt                2132
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_reduction        'Bruker SAINT+'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+2.4000P] 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         3134
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0813
_refine_ls_wR_factor_ref         0.1867
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_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
O1 O 0.69313(10) 0.9764(3) 0.88414(18) 0.0741(8) Uani 1 1 d . . .
O2 O 0.68146(7) 0.7646(2) 0.95390(15) 0.0509(6) Uani 1 1 d . . .
O3 O 0.63752(12) 0.1551(3) 0.98775(18) 0.0816(9) Uani 1 1 d . . .
H3 H 0.6539 0.1000 0.9589 0.098 Uiso 1 1 calc R . .
C1 C 0.5532(2) 0.6481(5) 1.1629(3) 0.0941(15) Uani 1 1 d . . .
H1A H 0.5554 0.6431 1.2252 0.113 Uiso 1 1 calc R . .
H1B H 0.5230 0.6326 1.1275 0.113 Uiso 1 1 calc R . .
C2 C 0.59307(16) 0.6772(4) 1.1250(2) 0.0609(10) Uani 1 1 d . . .
C3 C 0.64239(18) 0.7028(5) 1.1795(3) 0.0916(14) Uani 1 1 d . . .
H3A H 0.6399 0.6858 1.2419 0.110 Uiso 1 1 calc R . .
H3B H 0.6529 0.8059 1.1713 0.110 Uiso 1 1 calc R . .
H3C H 0.6660 0.6331 1.1604 0.110 Uiso 1 1 calc R . .
C4 C 0.59315(12) 0.6882(4) 1.0246(2) 0.0482(8) Uani 1 1 d . . .
H4 H 0.6069 0.7885 1.0129 0.058 Uiso 1 1 calc R . .
C5 C 0.54200(13) 0.6793(4) 0.9681(2) 0.0639(10) Uani 1 1 d . . .
H5A H 0.5282 0.5787 0.9758 0.077 Uiso 1 1 calc R . .
H5B H 0.5205 0.7535 0.9912 0.077 Uiso 1 1 calc R . .
C6 C 0.54170(13) 0.7085(5) 0.8673(2) 0.0665(10) Uani 1 1 d . . .
H6A H 0.5642 0.6366 0.8451 0.080 Uiso 1 1 calc R . .
H6B H 0.5088 0.6864 0.8370 0.080 Uiso 1 1 calc R . .
C7 C 0.55556(13) 0.8654(5) 0.8415(2) 0.0655(11) Uani 1 1 d . . .
C8 C 0.53377(15) 0.9936(5) 0.8880(3) 0.0853(13) Uani 1 1 d . . .
H8A H 0.4984 0.9880 0.8764 0.102 Uiso 1 1 calc R . .
H8B H 0.5446 1.0892 0.8661 0.102 Uiso 1 1 calc R . .
H8C H 0.5442 0.9864 0.9514 0.102 Uiso 1 1 calc R . .
C9 C 0.58319(15) 0.8994(5) 0.7763(3) 0.0766(12) Uani 1 1 d . . .
H9 H 0.5895 1.0031 0.7703 0.092 Uiso 1 1 calc R . .
C10 C 0.60468(15) 0.8018(5) 0.7141(3) 0.0798(12) Uani 1 1 d . . .
H10A H 0.5876 0.8202 0.6542 0.096 Uiso 1 1 calc R . .
H10B H 0.5987 0.6962 0.7292 0.096 Uiso 1 1 calc R . .
C11 C 0.66002(14) 0.8226(4) 0.7120(3) 0.0665(11) Uani 1 1 d . . .
H11A H 0.6692 0.7731 0.6589 0.080 Uiso 1 1 calc R . .
H11B H 0.6674 0.9307 0.7082 0.080 Uiso 1 1 calc R . .
C12 C 0.68984(12) 0.7568(4) 0.7935(2) 0.0533(9) Uani 1 1 d . . .
C13 C 0.68772(12) 0.8407(4) 0.8779(3) 0.0532(9) Uani 1 1 d . . .
C14 C 0.71797(12) 0.6328(4) 0.7932(3) 0.0604(10) Uani 1 1 d . . .
H14 H 0.7234 0.5924 0.7381 0.072 Uiso 1 1 calc R . .
C15 C 0.74139(12) 0.5547(4) 0.8769(3) 0.0687(11) Uani 1 1 d . . .
H15A H 0.7626 0.6255 0.9140 0.082 Uiso 1 1 calc R . .
H15B H 0.7613 0.4691 0.8619 0.082 Uiso 1 1 calc R . .
C16 C 0.70055(11) 0.4996(4) 0.9266(2) 0.0500(8) Uani 1 1 d . . .
C17 C 0.66919(11) 0.6077(4) 0.9555(2) 0.0453(8) Uani 1 1 d . . .
C18 C 0.62775(11) 0.5692(4) 0.9940(2) 0.0452(8) Uani 1 1 d . . .
C19 C 0.61801(13) 0.4147(4) 1.0033(2) 0.0544(9) Uani 1 1 d . . .
H19 H 0.5904 0.3846 1.0290 0.065 Uiso 1 1 calc R . .
C20 C 0.64892(14) 0.3043(4) 0.9745(2) 0.0565(9) Uani 1 1 d . . .
C21 C 0.68962(13) 0.3475(4) 0.9364(2) 0.0574(9) Uani 1 1 d . . .
H21 H 0.7101 0.2731 0.9169 0.069 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 0.0951(19) 0.0428(15) 0.088(2) -0.0137(14) 0.0261(16) -0.0161(14)
O2 0.0536(13) 0.0447(13) 0.0553(15) -0.0170(11) 0.0108(11) -0.0103(11)
O3 0.138(3) 0.0398(15) 0.0723(19) -0.0063(13) 0.0331(17) -0.0056(15)
C1 0.136(4) 0.088(3) 0.068(3) 0.002(2) 0.049(3) -0.005(3)
C2 0.092(3) 0.043(2) 0.051(2) -0.0019(17) 0.020(2) 0.0083(19)
C3 0.125(4) 0.094(3) 0.053(3) -0.016(2) 0.002(3) 0.026(3)
C4 0.057(2) 0.0391(18) 0.050(2) -0.0015(15) 0.0141(16) -0.0015(15)
C5 0.055(2) 0.067(2) 0.072(3) 0.004(2) 0.0178(19) -0.0057(18)
C6 0.054(2) 0.086(3) 0.057(2) -0.009(2) -0.0010(18) 0.010(2)
C7 0.053(2) 0.096(3) 0.047(2) 0.010(2) 0.0033(17) 0.003(2)
C8 0.077(3) 0.087(3) 0.093(3) 0.007(3) 0.017(3) 0.017(2)
C9 0.080(3) 0.080(3) 0.069(3) 0.004(2) 0.008(2) 0.002(2)
C10 0.072(3) 0.108(3) 0.059(3) 0.002(3) 0.011(2) 0.001(2)
C11 0.081(3) 0.060(2) 0.065(3) 0.000(2) 0.033(2) -0.008(2)
C12 0.054(2) 0.049(2) 0.061(2) -0.0099(18) 0.0203(18) -0.0139(17)
C13 0.0472(19) 0.040(2) 0.074(3) -0.0129(18) 0.0124(17) -0.0115(16)
C14 0.052(2) 0.062(2) 0.071(3) -0.022(2) 0.0253(19) -0.0132(18)
C15 0.045(2) 0.070(3) 0.093(3) -0.022(2) 0.015(2) 0.0063(18)
C16 0.0449(18) 0.050(2) 0.054(2) -0.0099(17) 0.0010(16) 0.0031(16)
C17 0.0482(18) 0.0400(18) 0.0462(19) -0.0099(15) 0.0011(15) -0.0048(15)
C18 0.0545(19) 0.0476(19) 0.0331(17) -0.0060(15) 0.0041(14) 0.0001(16)
C19 0.069(2) 0.048(2) 0.047(2) 0.0016(17) 0.0120(17) -0.0054(18)
C20 0.086(3) 0.0384(19) 0.045(2) -0.0037(16) 0.0087(19) -0.0014(18)
C21 0.065(2) 0.049(2) 0.055(2) -0.0099(17) 0.0003(18) 0.0145(18)

_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 1.198(4) . ?
O2 C13 1.352(4) . ?
O2 C17 1.414(4) . ?
O3 C20 1.363(4) . ?
C1 C2 1.319(5) . ?
C2 C3 1.497(6) . ?
C2 C4 1.512(5) . ?
C4 C18 1.519(4) . ?
C4 C5 1.536(5) . ?
C5 C6 1.535(5) . ?
C6 C7 1.489(5) . ?
C7 C9 1.348(5) . ?
C7 C8 1.488(5) . ?
C9 C10 1.448(5) . ?
C10 C11 1.527(5) . ?
C11 C12 1.493(5) . ?
C12 C14 1.330(5) . ?
C12 C13 1.473(5) . ?
C14 C15 1.497(5) . ?
C15 C16 1.503(5) . ?
C16 C21 1.376(5) . ?
C16 C17 1.385(4) . ?
C17 C18 1.380(4) . ?
C18 C19 1.388(4) . ?
C19 C20 1.389(5) . ?
C20 C21 1.371(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
C13 O2 C17 123.3(2) . . ?
C1 C2 C3 121.7(4) . . ?
C1 C2 C4 123.8(4) . . ?
C3 C2 C4 114.5(3) . . ?
C2 C4 C18 110.1(3) . . ?
C2 C4 C5 115.1(3) . . ?
C18 C4 C5 110.8(3) . . ?
C6 C5 C4 114.9(3) . . ?
C7 C6 C5 116.3(3) . . ?
C9 C7 C8 118.3(4) . . ?
C9 C7 C6 125.5(4) . . ?
C8 C7 C6 116.1(3) . . ?
C7 C9 C10 130.9(4) . . ?
C9 C10 C11 115.6(4) . . ?
C12 C11 C10 111.7(3) . . ?
C14 C12 C13 119.9(4) . . ?
C14 C12 C11 124.3(3) . . ?
C13 C12 C11 115.7(3) . . ?
O1 C13 O2 116.7(3) . . ?
O1 C13 C12 122.8(4) . . ?
O2 C13 C12 120.4(3) . . ?
C12 C14 C15 123.4(3) . . ?
C14 C15 C16 107.6(3) . . ?
C21 C16 C17 118.3(3) . . ?
C21 C16 C15 123.3(3) . . ?
C17 C16 C15 118.0(3) . . ?
C18 C17 C16 122.8(3) . . ?
C18 C17 O2 117.0(3) . . ?
C16 C17 O2 120.0(3) . . ?
C17 C18 C19 117.3(3) . . ?
C17 C18 C4 122.6(3) . . ?
C19 C18 C4 120.1(3) . . ?
C18 C19 C20 120.8(3) . . ?
O3 C20 C21 122.6(3) . . ?
O3 C20 C19 117.4(3) . . ?
C21 C20 C19 120.0(3) . . ?
C20 C21 C16 120.7(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
C1 C2 C4 C18 -120.1(4) . . . . ?
C3 C2 C4 C18 60.2(4) . . . . ?
C1 C2 C4 C5 6.0(5) . . . . ?
C3 C2 C4 C5 -173.8(3) . . . . ?
C2 C4 C5 C6 173.5(3) . . . . ?
C18 C4 C5 C6 -60.8(4) . . . . ?
C4 C5 C6 C7 -65.8(4) . . . . ?
C5 C6 C7 C9 141.1(4) . . . . ?
C5 C6 C7 C8 -43.5(5) . . . . ?
C8 C7 C9 C10 -173.0(4) . . . . ?
C6 C7 C9 C10 2.4(7) . . . . ?
C7 C9 C10 C11 -127.1(5) . . . . ?
C9 C10 C11 C12 73.5(5) . . . . ?
C10 C11 C12 C14 110.5(4) . . . . ?
C10 C11 C12 C13 -71.0(4) . . . . ?
C17 O2 C13 O1 172.7(3) . . . . ?
C17 O2 C13 C12 -9.9(4) . . . . ?
C14 C12 C13 O1 130.5(4) . . . . ?
C11 C12 C13 O1 -48.1(5) . . . . ?
C14 C12 C13 O2 -46.8(4) . . . . ?
C11 C12 C13 O2 134.6(3) . . . . ?
C13 C12 C14 C15 11.2(5) . . . . ?
C11 C12 C14 C15 -170.3(3) . . . . ?
C12 C14 C15 C16 61.9(4) . . . . ?
C14 C15 C16 C21 111.4(4) . . . . ?
C14 C15 C16 C17 -61.5(4) . . . . ?
C21 C16 C17 C18 0.3(5) . . . . ?
C15 C16 C17 C18 173.6(3) . . . . ?
C21 C16 C17 O2 174.5(3) . . . . ?
C15 C16 C17 O2 -12.3(5) . . . . ?
C13 O2 C17 C18 -125.1(3) . . . . ?
C13 O2 C17 C16 60.4(4) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
O2 C17 C18 C19 -174.3(3) . . . . ?
C16 C17 C18 C4 -179.3(3) . . . . ?
O2 C17 C18 C4 6.4(4) . . . . ?
C2 C4 C18 C17 -117.0(3) . . . . ?
C5 C4 C18 C17 114.5(3) . . . . ?
C2 C4 C18 C19 63.6(4) . . . . ?
C5 C4 C18 C19 -64.9(4) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C4 C18 C19 C20 179.2(3) . . . . ?
C18 C19 C20 O3 178.6(3) . . . . ?
C18 C19 C20 C21 -0.1(5) . . . . ?
O3 C20 C21 C16 -178.1(3) . . . . ?
C19 C20 C21 C16 0.5(5) . . . . ?
C17 C16 C21 C20 -0.6(5) . . . . ?
C15 C16 C21 C20 -173.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 0.82 1.98 2.795(4) 176.8 1_545

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.041