# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_global
#TrackingRef 'CIF for C23H18O4.cif'

_audit_creation_method           'APEX2 v2010.11-3'

data_I
#TrackingRef 'CIF for C23H18O4.cif'

_chemical_name_systematic        ?
_chemical_name_common            
7,7-Di(benzofuran-2-yl)-6-oxa-bicyclo[3.2.1]octan-4-ol
_chemical_formula_moiety         'C23 H18 O4'
_chemical_formula_sum            'C23 H18 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         358.37

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.594(7)
_cell_length_b                   12.392(8)
_cell_length_c                   13.698(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.41(2)
_cell_angle_gamma                90
_cell_volume                     1734.(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1466
_cell_measurement_theta_min      2.2538
_cell_measurement_theta_max      20.1045
_cell_measurement_temperature    270.(2)

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752

_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.6808
_exptl_absorpt_correction_T_max  0.7452

_exptl_special_details           
;
;

_diffrn_ambient_temperature      270.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              'fine focus'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'


_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            11037
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0981
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16

_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.
;

_reflns_number_total             3149
_reflns_number_gt                1449
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1540
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1534
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_refine_ls_number_reflns         3149
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0708P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.2'
_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 (Bruker AXS)'
_computing_publication_material  'SHELXTL (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.4844(2) -0.02324(18) 0.85050(14) 0.0602(7) Uani d . 1 . .
O O2 0.35822(19) 0.04261(16) 0.58827(14) 0.0510(6) Uani d . 1 . .
O O3 0.3612(3) 0.2620(3) 0.4447(2) 0.1216(12) Uani d . 1 . .
O O4 0.19821(19) 0.04400(16) 0.78775(14) 0.0501(6) Uani d . 1 . .
C C1 -0.1744(3) -0.0553(3) 0.7326(3) 0.0690(11) Uani d . 1 . .
H H1 -0.2602 -0.0803 0.7178 0.083 Uiso calc R 1 . .
C C2 -0.1106(3) -0.0569(3) 0.6592(3) 0.0611(10) Uani d . 1 . .
H H2 -0.152 -0.0815 0.5945 0.073 Uiso calc R 1 . .
C C3 0.0169(3) -0.0215(2) 0.6824(2) 0.0428(8) Uani d . 1 . .
C C4 0.1146(3) -0.0129(2) 0.6299(2) 0.0453(8) Uani d . 1 . .
H H4 0.1067 -0.0314 0.5628 0.054 Uiso calc R 1 . .
C C5 0.2195(3) 0.0265(2) 0.6952(2) 0.0411(8) Uani d . 1 . .
C C6 0.3553(3) 0.0483(2) 0.6919(2) 0.0435(8) Uani d . 1 . .
C C7 0.4430(3) -0.0382(3) 0.7478(2) 0.0434(8) Uani d . 1 . .
C C8 0.5603(3) -0.1112(3) 0.8873(2) 0.0501(9) Uani d . 1 . .
C C9 0.6241(3) -0.1284(3) 0.9861(2) 0.0704(11) Uani d . 1 . .
H H9 0.619 -0.0798 1.0366 0.085 Uiso calc R 1 . .
C C10 0.6956(3) -0.2200(3) 1.0069(3) 0.0709(11) Uani d . 1 . .
H H10 0.7407 -0.2352 1.0735 0.085 Uiso calc R 1 . .
C C11 0.4876(3) -0.1291(3) 0.7207(2) 0.0457(8) Uani d . 1 . .
H H11 0.4716 -0.1559 0.6551 0.055 Uiso calc R 1 . .
C C12 0.5648(3) -0.1789(3) 0.8101(2) 0.0446(8) Uani d . 1 . .
C C13 0.6389(3) -0.2715(3) 0.8331(2) 0.0576(9) Uani d . 1 . .
H H13 0.6453 -0.3196 0.7825 0.069 Uiso calc R 1 . .
C C14 0.7026(3) -0.2906(3) 0.9321(3) 0.0635(10) Uani d . 1 . .
H H14 0.752 -0.3532 0.949 0.076 Uiso calc R 1 . .
C C15 0.4390(4) 0.1288(3) 0.5686(3) 0.0684(10) Uani d . 1 . .
H H15 0.4971 0.1049 0.5279 0.082 Uiso calc R 1 . .
C C16 0.3509(4) 0.2178(3) 0.5191(3) 0.0841(13) Uani d . 1 . .
C C17 0.2516(4) 0.2515(3) 0.5731(3) 0.0752(11) Uani d . 1 . .
H H17A 0.2232 0.3245 0.5531 0.09 Uiso calc R 1 . .
H H17B 0.1758 0.2046 0.5527 0.09 Uiso calc R 1 . .
C C18 0.3040(3) 0.2471(3) 0.6856(3) 0.0656(10) Uani d . 1 . .
H H18A 0.2312 0.2359 0.715 0.079 Uiso calc R 1 . .
H H18B 0.3423 0.3166 0.7089 0.079 Uiso calc R 1 . .
C C19 0.4047(3) 0.1611(2) 0.7252(2) 0.0558(9) Uani d . 1 . .
H H19 0.439 0.1656 0.7989 0.067 Uiso calc R 1 . .
C C20 0.5146(3) 0.1695(3) 0.6723(3) 0.0685(10) Uani d . 1 . .
H H20A 0.5445 0.2432 0.6699 0.082 Uiso calc R 1 . .
H H20B 0.5883 0.1233 0.7033 0.082 Uiso calc R 1 . .
C C21 0.0716(3) 0.0140(2) 0.7783(2) 0.0452(8) Uani d . 1 . .
C C22 0.0087(4) 0.0184(3) 0.8525(2) 0.0634(10) Uani d . 1 . .
H H22 0.0491 0.0447 0.9168 0.076 Uiso calc R 1 . .
C C23 -0.1165(4) -0.0180(3) 0.8275(3) 0.0705(10) Uani d . 1 . .
H H23 -0.1636 -0.0175 0.876 0.085 Uiso calc R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0603(14) 0.0724(17) 0.0439(14) 0.0184(13) 0.0069(11) -0.0087(12)
O2 0.0546(14) 0.0564(15) 0.0446(13) -0.0129(11) 0.0179(10) -0.0021(11)
O3 0.169(3) 0.109(3) 0.098(2) -0.024(2) 0.056(2) 0.016(2)
O4 0.0440(14) 0.0633(15) 0.0423(13) -0.0034(11) 0.0104(10) -0.0066(11)
C1 0.047(2) 0.075(3) 0.087(3) -0.0056(19) 0.022(2) 0.016(2)
C2 0.051(2) 0.065(2) 0.065(2) -0.0095(18) 0.0105(19) 0.0033(19)
C3 0.0375(19) 0.0430(19) 0.046(2) 0.0003(16) 0.0079(15) 0.0044(15)
C4 0.0433(19) 0.051(2) 0.0408(18) -0.0045(16) 0.0092(16) -0.0015(15)
C5 0.0447(19) 0.0412(19) 0.0384(18) -0.0008(15) 0.0126(15) -0.0020(15)
C6 0.0424(19) 0.052(2) 0.0367(18) -0.0068(16) 0.0118(14) -0.0067(16)
C7 0.0359(18) 0.057(2) 0.0369(19) -0.0053(16) 0.0092(14) -0.0067(16)
C8 0.045(2) 0.058(2) 0.047(2) 0.0101(18) 0.0127(16) -0.0044(18)
C9 0.079(3) 0.084(3) 0.046(2) 0.025(2) 0.0119(19) -0.006(2)
C10 0.070(3) 0.083(3) 0.056(2) 0.018(2) 0.0101(19) 0.002(2)
C11 0.0438(19) 0.052(2) 0.0430(19) -0.0079(16) 0.0148(16) -0.0118(16)
C12 0.0370(18) 0.052(2) 0.047(2) -0.0076(16) 0.0157(15) -0.0057(18)
C13 0.052(2) 0.056(2) 0.064(3) -0.0048(18) 0.0153(18) -0.0101(18)
C14 0.058(2) 0.060(2) 0.071(3) 0.0085(18) 0.015(2) 0.002(2)
C15 0.067(2) 0.071(3) 0.076(3) -0.011(2) 0.035(2) 0.001(2)
C16 0.104(3) 0.083(3) 0.069(3) -0.032(3) 0.030(3) 0.006(3)
C17 0.089(3) 0.062(3) 0.077(3) 0.000(2) 0.026(2) 0.005(2)
C18 0.077(3) 0.048(2) 0.076(3) -0.008(2) 0.028(2) -0.0103(19)
C19 0.056(2) 0.051(2) 0.061(2) -0.0135(18) 0.0159(17) -0.0084(18)
C20 0.057(2) 0.065(2) 0.085(3) -0.0202(19) 0.021(2) -0.007(2)
C21 0.040(2) 0.047(2) 0.051(2) 0.0018(16) 0.0159(16) 0.0054(16)
C22 0.062(3) 0.080(3) 0.053(2) 0.005(2) 0.0240(18) 0.0007(19)
C23 0.064(3) 0.083(3) 0.077(3) 0.006(2) 0.041(2) 0.017(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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . 1.369(3) ?
O1 C7 . 1.370(3) ?
O2 C6 . 1.430(3) ?
O2 C15 . 1.438(4) ?
O3 C16 . 1.188(4) ?
O4 C5 . 1.363(3) ?
O4 C21 . 1.364(3) ?
C1 C2 . 1.352(4) ?
C1 C23 . 1.363(5) ?
C1 H1 . 0.93 ?
C2 C3 . 1.375(4) ?
C2 H2 . 0.93 ?
C3 C21 . 1.361(4) ?
C3 C4 . 1.412(4) ?
C4 C5 . 1.321(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.476(4) ?
C6 C7 . 1.490(4) ?
C6 C19 . 1.520(4) ?
C7 C11 . 1.313(4) ?
C8 C9 . 1.359(4) ?
C8 C12 . 1.360(4) ?
C9 C10 . 1.352(4) ?
C9 H9 . 0.93 ?
C10 C14 . 1.364(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.421(4) ?
C11 H11 . 0.93 ?
C12 C13 . 1.379(4) ?
C13 C14 . 1.366(4) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C15 C16 . 1.487(5) ?
C15 C20 . 1.519(4) ?
C15 H15 . 0.98 ?
C16 C17 . 1.496(5) ?
C17 C18 . 1.494(4) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 C19 . 1.503(4) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 C20 . 1.530(4) ?
C19 H19 . 0.98 ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
C21 C22 . 1.357(4) ?
C22 C23 . 1.356(5) ?
C22 H22 . 0.93 ?
C23 H23 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O1 C7 . . 105.5(2) ?
C6 O2 C15 . . 108.7(2) ?
C5 O4 C21 . . 105.7(2) ?
C2 C1 C23 . . 121.8(3) ?
C2 C1 H1 . . 119.1 ?
C23 C1 H1 . . 119.1 ?
C1 C2 C3 . . 118.6(3) ?
C1 C2 H2 . . 120.7 ?
C3 C2 H2 . . 120.7 ?
C21 C3 C2 . . 117.8(3) ?
C21 C3 C4 . . 106.6(3) ?
C2 C3 C4 . . 135.6(3) ?
C5 C4 C3 . . 106.4(3) ?
C5 C4 H4 . . 126.8 ?
C3 C4 H4 . . 126.8 ?
C4 C5 O4 . . 111.8(3) ?
C4 C5 C6 . . 134.3(3) ?
O4 C5 C6 . . 113.8(2) ?
O2 C6 C5 . . 107.4(2) ?
O2 C6 C7 . . 107.4(2) ?
C5 C6 C7 . . 109.5(2) ?
O2 C6 C19 . . 104.2(2) ?
C5 C6 C19 . . 114.8(3) ?
C7 C6 C19 . . 112.9(2) ?
C11 C7 O1 . . 111.5(3) ?
C11 C7 C6 . . 133.9(3) ?
O1 C7 C6 . . 114.6(3) ?
C9 C8 C12 . . 124.5(3) ?
C9 C8 O1 . . 125.4(3) ?
C12 C8 O1 . . 110.1(3) ?
C10 C9 C8 . . 116.4(3) ?
C10 C9 H9 . . 121.8 ?
C8 C9 H9 . . 121.8 ?
C9 C10 C14 . . 121.3(3) ?
C9 C10 H10 . . 119.4 ?
C14 C10 H10 . . 119.4 ?
C7 C11 C12 . . 107.2(3) ?
C7 C11 H11 . . 126.4 ?
C12 C11 H11 . . 126.4 ?
C8 C12 C13 . . 118.1(3) ?
C8 C12 C11 . . 105.8(3) ?
C13 C12 C11 . . 136.1(3) ?
C14 C13 C12 . . 118.2(3) ?
C14 C13 H13 . . 120.9 ?
C12 C13 H13 . . 120.9 ?
C10 C14 C13 . . 121.6(3) ?
C10 C14 H14 . . 119.2 ?
C13 C14 H14 . . 119.2 ?
O2 C15 C16 . . 107.6(3) ?
O2 C15 C20 . . 105.3(3) ?
C16 C15 C20 . . 106.9(3) ?
O2 C15 H15 . . 112.2 ?
C16 C15 H15 . . 112.2 ?
C20 C15 H15 . . 112.2 ?
O3 C16 C15 . . 122.9(5) ?
O3 C16 C17 . . 122.2(5) ?
C15 C16 C17 . . 114.9(4) ?
C18 C17 C16 . . 112.5(3) ?
C18 C17 H17A . . 109.1 ?
C16 C17 H17A . . 109.1 ?
C18 C17 H17B . . 109.1 ?
C16 C17 H17B . . 109.1 ?
H17A C17 H17B . . 107.8 ?
C17 C18 C19 . . 115.6(3) ?
C17 C18 H18A . . 108.4 ?
C19 C18 H18A . . 108.4 ?
C17 C18 H18B . . 108.4 ?
C19 C18 H18B . . 108.4 ?
H18A C18 H18B . . 107.5 ?
C18 C19 C6 . . 112.9(3) ?
C18 C19 C20 . . 109.7(3) ?
C6 C19 C20 . . 99.5(3) ?
C18 C19 H19 . . 111.4 ?
C6 C19 H19 . . 111.4 ?
C20 C19 H19 . . 111.4 ?
C15 C20 C19 . . 98.2(3) ?
C15 C20 H20A . . 112.1 ?
C19 C20 H20A . . 112.1 ?
C15 C20 H20B . . 112.1 ?
C19 C20 H20B . . 112.1 ?
H20A C20 H20B . . 109.8 ?
C22 C21 C3 . . 124.7(3) ?
C22 C21 O4 . . 125.7(3) ?
C3 C21 O4 . . 109.6(3) ?
C23 C22 C21 . . 116.1(3) ?
C23 C22 H22 . . 122.0 ?
C21 C22 H22 . . 122.0 ?
C22 C23 C1 . . 121.1(3) ?
C22 C23 H23 . . 119.5 ?
C1 C23 H23 . . 119.5 ?



_database_code_depnum_ccdc_archive 'CCDC 931682'