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


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# 
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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_120240
_database_code_depnum_ccdc_archive 'CCDC 896604'
#TrackingRef '120240.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 O2'
_chemical_formula_weight         292.36

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   'P b c a'
_symmetry_space_group_name_hall  '-P 2ac 2ab'

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

_cell_length_a                   8.9306(4)
_cell_length_b                   17.9709(7)
_cell_length_c                   19.8097(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3179.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1715
_cell_measurement_theta_min      2.7465
_cell_measurement_theta_max      20.1366

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8565
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_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 8.3333
_diffrn_reflns_number            24248
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_av_sigmaI/netI    0.0786
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         26.40
_reflns_number_total             3258
_reflns_number_gt                1389
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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^)+(0.1253P)^2^+0.4659P] 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       0.0053(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3258
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1806
_refine_ls_R_factor_gt           0.0731
_refine_ls_wR_factor_ref         0.2528
_refine_ls_wR_factor_gt          0.1961
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.0558(3) -0.02235(17) 0.06708(14) 0.0740(9) Uani 1 1 d . . .
O2 O 0.5281(3) 0.10277(17) 0.10519(16) 0.0811(10) Uani 1 1 d . . .
C1 C 0.0149(5) -0.1874(2) 0.1686(2) 0.0686(12) Uani 1 1 d . . .
H1 H -0.0517 -0.2269 0.1725 0.082 Uiso 1 1 calc R . .
C2 C -0.0105(5) -0.1328(2) 0.1224(2) 0.0662(12) Uani 1 1 d . . .
H2 H -0.0953 -0.1349 0.0952 0.079 Uiso 1 1 calc R . .
C3 C 0.0903(4) -0.0736(2) 0.11568(19) 0.0584(11) Uani 1 1 d . . .
C4 C 0.1334(6) 0.0455(3) 0.0716(3) 0.108(2) Uani 1 1 d . . .
H4A H 0.0884 0.0747 0.1075 0.130 Uiso 1 1 calc R . .
H4B H 0.1184 0.0726 0.0298 0.130 Uiso 1 1 calc R . .
C5 C 0.2925(4) 0.0409(2) 0.08423(19) 0.0534(10) Uani 1 1 d . . .
H5 H 0.3304 0.0134 0.0451 0.064 Uiso 1 1 calc R . .
C6 C 0.3842(5) 0.1083(3) 0.0848(2) 0.0788(14) Uani 1 1 d . . .
H6 H 0.3381 0.1381 0.1207 0.095 Uiso 1 1 calc R . .
C7 C 0.3746(4) 0.1589(2) 0.02470(18) 0.0534(10) Uani 1 1 d . . .
C8 C 0.4397(5) 0.1406(2) -0.0363(2) 0.0649(12) Uani 1 1 d . . .
H8 H 0.4907 0.0957 -0.0403 0.078 Uiso 1 1 calc R . .
C9 C 0.4313(5) 0.1867(3) -0.0910(2) 0.0741(13) Uani 1 1 d . . .
H9 H 0.4762 0.1732 -0.1315 0.089 Uiso 1 1 calc R . .
C10 C 0.3571(5) 0.2523(3) -0.0858(2) 0.0735(13) Uani 1 1 d . . .
H10 H 0.3525 0.2843 -0.1227 0.088 Uiso 1 1 calc R . .
C11 C 0.1397(5) -0.1840(2) 0.2099(2) 0.0663(12) Uani 1 1 d . . .
H11 H 0.1558 -0.2204 0.2425 0.080 Uiso 1 1 calc R . .
C12 C 0.2398(5) -0.1265(2) 0.20217(18) 0.0589(11) Uani 1 1 d . . .
H12 H 0.3239 -0.1250 0.2298 0.071 Uiso 1 1 calc R . .
C13 C 0.2201(4) -0.0705(2) 0.15476(17) 0.0487(9) Uani 1 1 d . . .
C14 C 0.5658(4) 0.0607(2) 0.16488(19) 0.0561(11) Uani 1 1 d . . .
C15 C 0.4523(4) 0.0011(2) 0.17820(18) 0.0517(10) Uani 1 1 d . . .
H15 H 0.4704 -0.0309 0.2142 0.062 Uiso 1 1 calc R . .
C16 C 0.3282(4) -0.00980(19) 0.14279(16) 0.0465(9) Uani 1 1 d . . .
C17 C 0.5783(6) 0.1130(3) 0.2245(2) 0.0817(14) Uani 1 1 d . . .
H17A H 0.6591 0.1473 0.2170 0.123 Uiso 1 1 calc R . .
H17B H 0.5975 0.0848 0.2648 0.123 Uiso 1 1 calc R . .
H17C H 0.4864 0.1401 0.2296 0.123 Uiso 1 1 calc R . .
C18 C 0.7174(4) 0.0268(3) 0.1492(2) 0.0774(14) Uani 1 1 d . . .
H18A H 0.7075 -0.0077 0.1125 0.116 Uiso 1 1 calc R . .
H18B H 0.7543 0.0012 0.1883 0.116 Uiso 1 1 calc R . .
H18C H 0.7862 0.0655 0.1367 0.116 Uiso 1 1 calc R . .
C19 C 0.2894(6) 0.2715(3) -0.0268(3) 0.0804(14) Uani 1 1 d . . .
H19 H 0.2374 0.3162 -0.0238 0.097 Uiso 1 1 calc R . .
C20 C 0.2974(5) 0.2255(3) 0.0280(2) 0.0708(13) Uani 1 1 d . . .
H20 H 0.2504 0.2392 0.0680 0.085 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 0.0657(19) 0.075(2) 0.0811(19) 0.0294(17) -0.0276(14) -0.0232(16)
O2 0.0528(18) 0.089(2) 0.102(2) 0.0504(18) -0.0299(15) -0.0186(15)
C1 0.069(3) 0.058(3) 0.079(3) 0.004(3) 0.013(2) -0.014(2)
C2 0.057(3) 0.067(3) 0.075(3) 0.002(2) -0.004(2) -0.013(2)
C3 0.057(3) 0.058(3) 0.060(2) 0.004(2) 0.0013(19) -0.004(2)
C4 0.093(4) 0.096(4) 0.135(4) 0.050(3) -0.056(4) -0.031(3)
C5 0.043(2) 0.053(2) 0.064(2) 0.0130(19) -0.0099(18) 0.0004(18)
C6 0.073(3) 0.084(3) 0.079(3) 0.035(2) -0.033(2) -0.025(3)
C7 0.053(2) 0.054(3) 0.053(2) 0.0107(19) -0.0110(19) -0.010(2)
C8 0.067(3) 0.057(3) 0.071(3) 0.003(2) -0.003(2) 0.014(2)
C9 0.072(3) 0.088(4) 0.061(3) 0.007(3) 0.003(2) 0.005(3)
C10 0.079(3) 0.071(3) 0.070(3) 0.027(2) -0.013(3) -0.001(3)
C11 0.073(3) 0.054(3) 0.072(3) 0.018(2) 0.012(2) 0.003(2)
C12 0.058(3) 0.058(3) 0.061(2) 0.008(2) 0.0005(19) 0.002(2)
C13 0.050(2) 0.048(2) 0.0486(19) 0.0020(18) 0.0025(18) 0.0025(18)
C14 0.053(2) 0.053(2) 0.062(2) 0.016(2) -0.0181(19) -0.0005(19)
C15 0.054(2) 0.049(2) 0.052(2) 0.0108(18) -0.0071(18) 0.0038(18)
C16 0.047(2) 0.044(2) 0.0485(19) 0.0071(17) -0.0007(17) 0.0053(17)
C17 0.090(3) 0.067(3) 0.088(3) -0.007(3) -0.020(3) -0.009(3)
C18 0.044(2) 0.091(4) 0.098(3) 0.017(3) -0.012(2) 0.005(2)
C19 0.089(3) 0.051(3) 0.101(4) 0.008(3) -0.007(3) 0.018(3)
C20 0.080(3) 0.070(3) 0.062(3) -0.004(2) 0.005(2) 0.010(3)

_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 C3 1.368(5) . ?
O1 C4 1.406(5) . ?
O2 C6 1.352(5) . ?
O2 C14 1.443(4) . ?
C1 C2 1.361(6) . ?
C1 C11 1.383(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.400(5) . ?
C2 H2 0.9300 . ?
C3 C13 1.395(5) . ?
C4 C5 1.445(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.463(5) . ?
C5 C16 1.509(5) . ?
C5 H5 0.9800 . ?
C6 C7 1.499(5) . ?
C6 H6 0.9800 . ?
C7 C8 1.381(5) . ?
C7 C20 1.384(6) . ?
C8 C9 1.366(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.356(6) . ?
C9 H9 0.9300 . ?
C10 C19 1.360(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(5) . ?
C12 H12 0.9300 . ?
C13 C16 1.475(5) . ?
C14 C15 1.498(5) . ?
C14 C17 1.514(6) . ?
C14 C18 1.517(5) . ?
C15 C16 1.327(5) . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.367(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
C3 O1 C4 115.3(3) . . ?
C6 O2 C14 120.4(3) . . ?
C2 C1 C11 120.1(4) . . ?
C2 C1 H1 120.0 . . ?
C11 C1 H1 120.0 . . ?
C1 C2 C3 120.3(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O1 C3 C13 123.4(3) . . ?
O1 C3 C2 115.7(4) . . ?
C13 C3 C2 120.8(4) . . ?
O1 C4 C5 116.5(4) . . ?
O1 C4 H4A 108.2 . . ?
C5 C4 H4A 108.2 . . ?
O1 C4 H4B 108.2 . . ?
C5 C4 H4B 108.2 . . ?
H4A C4 H4B 107.3 . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 C16 112.0(3) . . ?
C6 C5 C16 112.1(3) . . ?
C4 C5 H5 103.4 . . ?
C6 C5 H5 103.4 . . ?
C16 C5 H5 103.4 . . ?
O2 C6 C5 118.2(4) . . ?
O2 C6 C7 109.7(3) . . ?
C5 C6 C7 117.7(3) . . ?
O2 C6 H6 102.8 . . ?
C5 C6 H6 102.8 . . ?
C7 C6 H6 102.8 . . ?
C8 C7 C20 117.2(3) . . ?
C8 C7 C6 121.8(4) . . ?
C20 C7 C6 121.0(4) . . ?
C9 C8 C7 121.8(4) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C19 120.1(4) . . ?
C9 C10 H10 119.9 . . ?
C19 C10 H10 119.9 . . ?
C12 C11 C1 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C1 C11 H11 120.3 . . ?
C11 C12 C13 122.6(4) . . ?
C11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C12 C13 C3 116.8(4) . . ?
C12 C13 C16 124.2(3) . . ?
C3 C13 C16 119.0(3) . . ?
O2 C14 C15 111.2(3) . . ?
O2 C14 C17 109.4(3) . . ?
C15 C14 C17 110.9(3) . . ?
O2 C14 C18 104.5(3) . . ?
C15 C14 C18 110.6(3) . . ?
C17 C14 C18 110.1(3) . . ?
C16 C15 C14 125.3(3) . . ?
C16 C15 H15 117.4 . . ?
C14 C15 H15 117.4 . . ?
C15 C16 C13 124.8(3) . . ?
C15 C16 C5 119.6(3) . . ?
C13 C16 C5 115.6(3) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 C20 120.4(4) . . ?
C10 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C7 120.7(4) . . ?
C19 C20 H20 119.6 . . ?
C7 C20 H20 119.6 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.049