# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

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#
#                 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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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_cd21386

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 O'
_chemical_formula_weight         310.37

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   P2(1)2(1)2(1)

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'

_cell_length_a                   6.1046(6)
_cell_length_b                   15.4141(15)
_cell_length_c                   17.5871(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1654.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3137
_cell_measurement_theta_min      4.632
_cell_measurement_theta_max      49.614

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.112
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.37989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  '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_%        ?
_diffrn_reflns_number            10077
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3260
_reflns_number_gt                2837
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0483P)²+0.0852P] where P=(Fo²+2Fc²)/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'
_refine_ls_abs_structure_Flack   0.7(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3260
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_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 -0.0162(2) 0.28588(9) 0.69784(6) 0.0599(3) Uani 1 1 d . . .
C1 C 0.3424(2) 0.32987(9) 0.90149(8) 0.0375(3) Uani 1 1 d . . .
C2 C 0.2795(3) 0.39151(10) 0.95423(9) 0.0442(4) Uani 1 1 d . . .
H2 H 0.1406 0.4162 0.9522 0.053 Uiso 1 1 calc R . .
C3 C 0.4261(3) 0.41579(11) 1.00985(9) 0.0530(4) Uani 1 1 d . . .
H3 H 0.3853 0.4568 1.0459 0.064 Uiso 1 1 calc R . .
C4 C 0.6328(3) 0.37984(12) 1.01257(9) 0.0545(5) Uani 1 1 d . . .
H4 H 0.7299 0.3969 1.0505 0.065 Uiso 1 1 calc R . .
C5 C 0.6970(3) 0.31882(11) 0.95967(9) 0.0480(4) Uani 1 1 d . . .
H5 H 0.8367 0.2948 0.9616 0.058 Uiso 1 1 calc R . .
C6 C 0.5511(2) 0.29390(10) 0.90396(8) 0.0386(3) Uani 1 1 d . . .
C7 C 0.5799(2) 0.22679(11) 0.84297(8) 0.0426(4) Uani 1 1 d . . .
H7A H 0.6063 0.1701 0.8650 0.051 Uiso 1 1 calc R . .
H7B H 0.7017 0.2416 0.8100 0.051 Uiso 1 1 calc R . .
C8 C 0.3646(2) 0.22784(9) 0.79904(8) 0.0365(3) Uani 1 1 d . . .
C9 C 0.2188(2) 0.29379(9) 0.83617(8) 0.0371(3) Uani 1 1 d . . .
H9 H 0.0614 0.2825 0.8410 0.045 Uiso 1 1 calc R . .
C10 C 0.3155(3) 0.31431(10) 0.75938(8) 0.0406(3) Uani 1 1 d . . .
H10 H 0.4345 0.3570 0.7585 0.049 Uiso 1 1 calc R . .
C11 C 0.1710(3) 0.31229(10) 0.69228(9) 0.0440(4) Uani 1 1 d . . .
C12 C 0.2590(3) 0.33983(10) 0.61720(9) 0.0478(4) Uani 1 1 d . . .
C13 C 0.4642(4) 0.37553(15) 0.60664(12) 0.0704(6) Uani 1 1 d . . .
H13 H 0.5557 0.3845 0.6482 0.084 Uiso 1 1 calc R . .
C14 C 0.5339(4) 0.39792(16) 0.53461(14) 0.0855(7) Uani 1 1 d . . .
H14 H 0.6718 0.4223 0.5278 0.103 Uiso 1 1 calc R . .
C15 C 0.4014(6) 0.38446(16) 0.47343(13) 0.0898(8) Uani 1 1 d . . .
H15 H 0.4493 0.3995 0.4250 0.108 Uiso 1 1 calc R . .
C16 C 0.1996(6) 0.34922(16) 0.48302(12) 0.0892(8) Uani 1 1 d . . .
H16 H 0.1097 0.3397 0.4411 0.107 Uiso 1 1 calc R . .
C17 C 0.1282(4) 0.32766(13) 0.55434(10) 0.0680(6) Uani 1 1 d . . .
H17 H -0.0112 0.3044 0.5604 0.082 Uiso 1 1 calc R . .
C18 C 0.2927(3) 0.14485(9) 0.76383(8) 0.0385(3) Uani 1 1 d . . .
C19 C 0.4291(3) 0.10382(12) 0.71242(10) 0.0575(5) Uani 1 1 d . . .
H19 H 0.5618 0.1295 0.6994 0.069 Uiso 1 1 calc R . .
C20 C 0.3719(4) 0.02571(13) 0.68017(12) 0.0719(6) Uani 1 1 d . . .
H20 H 0.4649 -0.0005 0.6452 0.086 Uiso 1 1 calc R . .
C21 C 0.1800(4) -0.01314(12) 0.69925(12) 0.0680(6) Uani 1 1 d . . .
H21 H 0.1420 -0.0662 0.6778 0.082 Uiso 1 1 calc R . .
C22 C 0.0436(3) 0.02599(12) 0.74996(12) 0.0649(5) Uani 1 1 d . . .
H22 H -0.0878 -0.0006 0.7631 0.078 Uiso 1 1 calc R . .
C23 C 0.0985(3) 0.10478(11) 0.78202(10) 0.0489(4) Uani 1 1 d . . .
H23 H 0.0032 0.1310 0.8163 0.059 Uiso 1 1 calc R . .


_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 C11 1.217(2) . ?
C1 C2 1.382(2) . ?
C1 C6 1.390(2) . ?
C1 C9 1.483(2) . ?
C2 C3 1.378(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.501(2) . ?
C7 C8 1.525(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C18 1.487(2) . ?
C8 C9 1.5006(19) . ?
C8 C10 1.534(2) . ?
C9 C10 1.507(2) . ?
C9 H9 0.9800 . ?
C10 C11 1.474(2) . ?
C10 H10 0.9800 . ?
C11 C12 1.487(2) . ?
C12 C17 1.377(3) . ?
C12 C13 1.381(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.357(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.374(2) . ?
C18 C19 1.382(2) . ?
C19 C20 1.376(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.358(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.361(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(2) . ?
C22 H22 0.9300 . ?
C23 H23 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
C2 C1 C6 120.52(14) . . ?
C2 C1 C9 129.52(14) . . ?
C6 C1 C9 109.94(13) . . ?
C3 C2 C1 118.86(16) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.66(17) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.70(16) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 119.06(16) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 120.20(15) . . ?
C5 C6 C7 128.65(14) . . ?
C1 C6 C7 111.10(13) . . ?
C6 C7 C8 104.71(12) . . ?
C6 C7 H7A 110.8 . . ?
C8 C7 H7A 110.8 . . ?
C6 C7 H7B 110.8 . . ?
C8 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C18 C8 C9 126.06(13) . . ?
C18 C8 C7 117.15(12) . . ?
C9 C8 C7 107.33(11) . . ?
C18 C8 C10 120.02(11) . . ?
C9 C8 C10 59.56(9) . . ?
C7 C8 C10 114.08(13) . . ?
C1 C9 C8 106.83(12) . . ?
C1 C9 C10 114.59(12) . . ?
C8 C9 C10 61.32(10) . . ?
C1 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 118.60(13) . . ?
C11 C10 C8 117.57(12) . . ?
C9 C10 C8 59.12(9) . . ?
C11 C10 H10 116.4 . . ?
C9 C10 H10 116.4 . . ?
C8 C10 H10 116.4 . . ?
O1 C11 C10 120.31(15) . . ?
O1 C11 C12 120.40(15) . . ?
C10 C11 C12 119.25(14) . . ?
C17 C12 C13 118.21(18) . . ?
C17 C12 C11 117.67(16) . . ?
C13 C12 C11 124.11(16) . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 121.2(2) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C23 C18 C19 117.78(15) . . ?
C23 C18 C8 122.97(14) . . ?
C19 C18 C8 119.20(14) . . ?
C20 C19 C18 121.14(18) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C21 C20 C19 120.20(18) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 119.62(17) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 120.59(18) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C18 C23 C22 120.66(16) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?

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
C6 C1 C2 C3 -0.9(2) . . . . ?
C9 C1 C2 C3 -179.04(14) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C4 C5 C6 C7 -177.21(15) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C9 C1 C6 C5 179.15(13) . . . . ?
C2 C1 C6 C7 178.22(13) . . . . ?
C9 C1 C6 C7 -3.27(16) . . . . ?
C5 C6 C7 C8 179.79(14) . . . . ?
C1 C6 C7 C8 2.47(16) . . . . ?
C6 C7 C8 C18 -149.29(12) . . . . ?
C6 C7 C8 C9 -0.74(15) . . . . ?
C6 C7 C8 C10 63.03(15) . . . . ?
C2 C1 C9 C8 -178.99(14) . . . . ?
C6 C1 C9 C8 2.68(16) . . . . ?
C2 C1 C9 C10 115.41(17) . . . . ?
C6 C1 C9 C10 -62.93(16) . . . . ?
C18 C8 C9 C1 143.87(13) . . . . ?
C7 C8 C9 C1 -1.08(15) . . . . ?
C10 C8 C9 C1 -109.28(13) . . . . ?
C18 C8 C9 C10 -106.85(15) . . . . ?
C7 C8 C9 C10 108.20(13) . . . . ?
C1 C9 C10 C11 -156.79(13) . . . . ?
C8 C9 C10 C11 106.75(15) . . . . ?
C1 C9 C10 C8 96.46(14) . . . . ?
C18 C8 C10 C11 8.20(19) . . . . ?
C9 C8 C10 C11 -108.48(15) . . . . ?
C7 C8 C10 C11 154.86(13) . . . . ?
C18 C8 C10 C9 116.68(15) . . . . ?
C7 C8 C10 C9 -96.65(13) . . . . ?
C9 C10 C11 O1 -7.5(2) . . . . ?
C8 C10 C11 O1 60.5(2) . . . . ?
C9 C10 C11 C12 174.70(13) . . . . ?
C8 C10 C11 C12 -117.31(15) . . . . ?
O1 C11 C12 C17 -5.2(2) . . . . ?
C10 C11 C12 C17 172.60(16) . . . . ?
O1 C11 C12 C13 175.81(18) . . . . ?
C10 C11 C12 C13 -6.4(2) . . . . ?
C17 C12 C13 C14 -0.1(3) . . . . ?
C11 C12 C13 C14 178.93(18) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C15 C16 C17 C12 -1.0(4) . . . . ?
C13 C12 C17 C16 0.8(3) . . . . ?
C11 C12 C17 C16 -178.30(19) . . . . ?
C9 C8 C18 C23 -22.0(2) . . . . ?
C7 C8 C18 C23 119.93(16) . . . . ?
C10 C8 C18 C23 -94.39(17) . . . . ?
C9 C8 C18 C19 160.36(15) . . . . ?
C7 C8 C18 C19 -57.67(19) . . . . ?
C10 C8 C18 C19 88.01(18) . . . . ?
C23 C18 C19 C20 0.4(3) . . . . ?
C8 C18 C19 C20 178.10(17) . . . . ?
C18 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C19 C18 C23 C22 0.3(3) . . . . ?
C8 C18 C23 C22 -177.34(16) . . . . ?
C21 C22 C23 C18 -0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.025
_database_code_depnum_ccdc_archive 'CCDC 962017'
