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


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#
#                 Cambridge Crystallographic Data Centre
#                                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 retrieval see:
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data_1
_database_code_depnum_ccdc_archive 'CCDC 870917'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 O'
_chemical_formula_sum            'C17 H18 O'
_chemical_formula_weight         238.31

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'
O O 0.0106 0.0060 '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'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

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

_cell_length_a                   14.4230(19)
_cell_length_b                   6.1054(8)
_cell_length_c                   30.487(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2684.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2403
_cell_measurement_theta_min      3.009
_cell_measurement_theta_max      27.810

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9961
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2357
_reflns_number_gt                1859
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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^)+(0.0534P)^2^+0.5588P] 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         2357
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.006
_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 0.87548(7) 0.11833(17) 0.74364(3) 0.0325(3) Uani 1 1 d . . .
C4 C 0.88757(9) 0.3750(2) 0.87046(5) 0.0266(3) Uani 1 1 d . . .
C10 C 0.86685(9) 0.3901(2) 1.03205(5) 0.0256(3) Uani 1 1 d . . .
C2 C 0.83323(10) 0.0902(2) 0.82103(5) 0.0292(3) Uani 1 1 d . . .
H2 H 0.8002 -0.0388 0.8167 0.035 Uiso 1 1 calc R . .
C3 C 0.83953(10) 0.1810(3) 0.86245(5) 0.0297(4) Uani 1 1 d . . .
H3 H 0.8107 0.1102 0.8858 0.036 Uiso 1 1 calc R . .
C1 C 0.87665(9) 0.1929(2) 0.78607(5) 0.0255(3) Uani 1 1 d . . .
C13 C 0.89115(9) 0.1258(2) 1.10709(5) 0.0270(3) Uani 1 1 d . . .
C14 C 0.85071(9) 0.3312(2) 1.10992(5) 0.0281(3) Uani 1 1 d . . .
H14 H 0.8315 0.3829 1.1371 0.034 Uiso 1 1 calc R . .
C6 C 0.92560(9) 0.3852(2) 0.79303(5) 0.0280(4) Uani 1 1 d . . .
H6 H 0.9549 0.4545 0.7697 0.034 Uiso 1 1 calc R . .
C9 C 0.85553(11) 0.5398(3) 0.99281(5) 0.0327(4) Uani 1 1 d . . .
H9A H 0.8013 0.6306 0.9975 0.039 Uiso 1 1 calc R . .
H9B H 0.9089 0.6363 0.9915 0.039 Uiso 1 1 calc R . .
C12 C 0.91897(10) 0.0547(2) 1.06600(5) 0.0292(4) Uani 1 1 d . . .
H12 H 0.9464 -0.0824 1.0632 0.035 Uiso 1 1 calc R . .
C15 C 0.83827(9) 0.4609(2) 1.07327(5) 0.0274(3) Uani 1 1 d . . .
H15 H 0.8104 0.5975 1.0762 0.033 Uiso 1 1 calc R . .
C7 C 0.89550(10) 0.4743(3) 0.91418(5) 0.0289(3) Uani 1 1 d . . .
H7 H 0.9407 0.5816 0.9175 0.035 Uiso 1 1 calc R . .
C11 C 0.90677(10) 0.1835(2) 1.02907(5) 0.0281(3) Uani 1 1 d . . .
H11 H 0.9256 0.1310 1.0019 0.034 Uiso 1 1 calc R . .
C8 C 0.84563(10) 0.4285(3) 0.94940(5) 0.0320(4) Uani 1 1 d . . .
H8 H 0.8011 0.3189 0.9470 0.038 Uiso 1 1 calc R . .
C5 C 0.93081(9) 0.4738(2) 0.83452(5) 0.0280(4) Uani 1 1 d . . .
H5 H 0.9640 0.6027 0.8387 0.034 Uiso 1 1 calc R . .
C16 C 0.90298(11) -0.0159(3) 1.14725(5) 0.0373(4) Uani 1 1 d . . .
H16A H 0.8756 0.0557 1.1721 0.056 Uiso 1 1 calc R . .
H16B H 0.9678 -0.0392 1.1526 0.056 Uiso 1 1 calc R . .
H16C H 0.8730 -0.1544 1.1426 0.056 Uiso 1 1 calc R . .
C17 C 0.82714(12) -0.0799(3) 0.73542(5) 0.0405(4) Uani 1 1 d . . .
H17A H 0.8520 -0.1940 0.7536 0.061 Uiso 1 1 calc R . .
H17B H 0.8342 -0.1196 0.7051 0.061 Uiso 1 1 calc R . .
H17C H 0.7626 -0.0602 0.7419 0.061 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 0.0382(6) 0.0321(6) 0.0272(6) -0.0013(5) 0.0056(4) -0.0006(5)
C4 0.0212(7) 0.0289(8) 0.0296(8) 0.0028(7) -0.0022(6) 0.0006(6)
C10 0.0219(7) 0.0271(8) 0.0279(8) -0.0016(6) -0.0021(6) -0.0004(6)
C2 0.0290(8) 0.0273(8) 0.0311(8) 0.0010(7) 0.0016(6) -0.0043(7)
C3 0.0287(8) 0.0322(8) 0.0282(8) 0.0053(6) 0.0033(6) -0.0058(7)
C1 0.0233(7) 0.0287(8) 0.0246(8) 0.0012(6) 0.0008(6) 0.0060(6)
C13 0.0224(7) 0.0294(8) 0.0292(8) 0.0009(7) -0.0022(6) -0.0043(6)
C14 0.0282(8) 0.0330(8) 0.0231(7) -0.0061(6) 0.0003(6) -0.0016(6)
C6 0.0235(7) 0.0314(8) 0.0290(8) 0.0093(7) 0.0026(6) -0.0005(6)
C9 0.0374(9) 0.0305(8) 0.0303(8) 0.0005(7) -0.0016(6) 0.0049(7)
C12 0.0287(7) 0.0250(7) 0.0341(8) -0.0024(7) 0.0011(6) 0.0032(6)
C15 0.0252(7) 0.0240(7) 0.0330(8) -0.0062(6) -0.0010(6) 0.0018(6)
C7 0.0260(7) 0.0291(8) 0.0317(8) 0.0024(7) -0.0041(6) -0.0021(6)
C11 0.0287(7) 0.0297(8) 0.0257(7) -0.0057(7) 0.0023(6) 0.0014(7)
C8 0.0308(8) 0.0352(9) 0.0299(8) 0.0035(7) -0.0040(6) -0.0029(7)
C5 0.0226(7) 0.0277(8) 0.0339(8) 0.0047(7) -0.0020(6) -0.0033(6)
C16 0.0399(9) 0.0373(9) 0.0346(9) 0.0047(8) -0.0012(7) -0.0014(8)
C17 0.0569(11) 0.0317(9) 0.0330(9) -0.0062(7) 0.0027(7) -0.0050(8)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3714(17) . ?
O1 C17 1.4189(19) . ?
C4 C3 1.394(2) . ?
C4 C5 1.397(2) . ?
C4 C7 1.469(2) . ?
C10 C11 1.390(2) . ?
C10 C15 1.391(2) . ?
C10 C9 1.514(2) . ?
C2 C3 1.382(2) . ?
C2 C1 1.386(2) . ?
C1 C6 1.386(2) . ?
C13 C12 1.385(2) . ?
C13 C14 1.386(2) . ?
C13 C16 1.509(2) . ?
C14 C15 1.382(2) . ?
C6 C5 1.378(2) . ?
C9 C8 1.495(2) . ?
C12 C11 1.385(2) . ?
C7 C8 1.322(2) . ?

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
C1 O1 C17 117.12(12) . . ?
C3 C4 C5 116.82(14) . . ?
C3 C4 C7 123.26(13) . . ?
C5 C4 C7 119.91(13) . . ?
C11 C10 C15 117.63(14) . . ?
C11 C10 C9 122.75(13) . . ?
C15 C10 C9 119.61(13) . . ?
C3 C2 C1 119.41(14) . . ?
C2 C3 C4 122.26(14) . . ?
O1 C1 C6 115.58(12) . . ?
O1 C1 C2 124.70(13) . . ?
C6 C1 C2 119.72(13) . . ?
C12 C13 C14 117.51(14) . . ?
C12 C13 C16 121.42(14) . . ?
C14 C13 C16 121.07(13) . . ?
C15 C14 C13 121.54(14) . . ?
C5 C6 C1 120.03(13) . . ?
C8 C9 C10 115.80(13) . . ?
C11 C12 C13 121.37(14) . . ?
C14 C15 C10 120.93(13) . . ?
C8 C7 C4 127.40(14) . . ?
C12 C11 C10 121.00(13) . . ?
C7 C8 C9 124.82(15) . . ?
C6 C5 C4 121.75(14) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.039