# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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:
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#  from this site to visualise CIF-encoded structures and 
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data_p21c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 O2'
_chemical_formula_weight         236.26

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   P2(1)/c

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

_cell_length_a                   14.927(5)
_cell_length_b                   6.570(2)
_cell_length_c                   13.515(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.131(3)
_cell_angle_gamma                90.00
_cell_volume                     1190.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2691
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      26.21

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_T_max  0.9738
_exptl_absorpt_process_details   SADABS

_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8061
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2207
_reflns_number_gt                1549
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0400P)²+0.5018P] 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     SHELXL
_refine_ls_extinction_coef       0.0076(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2207
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
C1 C 0.63137(16) 0.3227(3) 0.15866(17) 0.0457(5) Uani 1 1 d . . .
C3 C 0.46712(15) 0.1780(3) 0.10214(16) 0.0416(5) Uani 1 1 d . . .
C4 C 0.36616(16) 0.2141(4) 0.05640(18) 0.0538(6) Uani 1 1 d . . .
H4 H 0.3410 0.3445 0.0344 0.065 Uiso 1 1 calc R . .
C5 C 0.30312(17) 0.0535(4) 0.04387(19) 0.0576(7) Uani 1 1 d . . .
H5 H 0.2347 0.0761 0.0145 0.069 Uiso 1 1 calc R . .
C6 C 0.34000(16) -0.1414(4) 0.07438(18) 0.0536(6) Uani 1 1 d . . .
H6 H 0.2965 -0.2494 0.0642 0.064 Uiso 1 1 calc R . .
C7 C 0.44086(16) -0.1747(3) 0.11964(17) 0.0466(5) Uani 1 1 d . . .
H7 H 0.4655 -0.3059 0.1400 0.056 Uiso 1 1 calc R . .
C8 C 0.50703(14) -0.0146(3) 0.13562(15) 0.0373(5) Uani 1 1 d . . .
C9 C 0.61294(15) -0.0347(3) 0.18595(16) 0.0396(5) Uani 1 1 d . . .
H9 H 0.6404 -0.1628 0.2101 0.048 Uiso 1 1 calc R . .
C10 C 0.67534(15) 0.1228(3) 0.20022(15) 0.0388(5) Uani 1 1 d . . .
C11 C 0.78530(15) 0.0992(3) 0.25436(16) 0.0418(5) Uani 1 1 d . . .
C12 C 0.82738(16) -0.0889(3) 0.25384(18) 0.0494(6) Uani 1 1 d . . .
H12 H 0.7861 -0.1971 0.2165 0.059 Uiso 1 1 calc R . .
C13 C 0.92948(16) -0.1188(4) 0.30771(19) 0.0547(6) Uani 1 1 d . . .
H13 H 0.9552 -0.2467 0.3054 0.066 Uiso 1 1 calc R . .
C14 C 0.99407(16) 0.0352(4) 0.36462(17) 0.0523(6) Uani 1 1 d . . .
C15 C 0.95242(17) 0.2229(4) 0.36524(19) 0.0581(6) Uani 1 1 d . . .
H15 H 0.9942 0.3303 0.4028 0.070 Uiso 1 1 calc R . .
C16 C 0.85081(16) 0.2558(4) 0.31184(18) 0.0520(6) Uani 1 1 d . . .
H16 H 0.8256 0.3842 0.3142 0.062 Uiso 1 1 calc R . .
C17 C 1.10507(16) 0.0012(5) 0.4229(2) 0.0704(8) Uani 1 1 d . . .
H17A H 1.1369 0.0785 0.3870 0.106 Uiso 1 1 calc R . .
H17B H 1.1191 -0.1408 0.4205 0.106 Uiso 1 1 calc R . .
H17C H 1.1299 0.0442 0.4982 0.106 Uiso 1 1 calc R . .
O1 O 0.67606(12) 0.4762(2) 0.15956(14) 0.0650(5) Uani 1 1 d . . .
O3 O 0.52922(11) 0.3399(2) 0.11374(12) 0.0505(4) Uani 1 1 d . . .

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
C1 0.0497(13) 0.0366(12) 0.0504(12) 0.0012(9) 0.0216(10) 0.0007(10)
C3 0.0451(12) 0.0372(11) 0.0416(11) 0.0017(9) 0.0183(9) 0.0038(10)
C4 0.0479(14) 0.0504(14) 0.0570(13) 0.0086(11) 0.0176(11) 0.0133(11)
C5 0.0402(13) 0.0695(17) 0.0564(14) 0.0067(12) 0.0152(11) 0.0069(12)
C6 0.0443(13) 0.0602(15) 0.0553(13) 0.0011(11) 0.0211(11) -0.0080(11)
C7 0.0480(13) 0.0405(12) 0.0508(12) 0.0043(10) 0.0212(10) 0.0005(10)
C8 0.0400(12) 0.0354(11) 0.0384(10) -0.0002(9) 0.0191(9) 0.0027(9)
C9 0.0430(12) 0.0312(11) 0.0459(11) 0.0034(9) 0.0207(9) 0.0057(9)
C10 0.0445(12) 0.0322(11) 0.0417(11) -0.0003(9) 0.0207(9) 0.0015(9)
C11 0.0438(12) 0.0388(12) 0.0441(11) 0.0018(9) 0.0206(9) -0.0018(10)
C12 0.0434(13) 0.0462(13) 0.0543(13) -0.0049(10) 0.0176(10) 0.0012(10)
C13 0.0472(14) 0.0564(15) 0.0599(14) -0.0001(12) 0.0230(11) 0.0069(12)
C14 0.0408(13) 0.0688(16) 0.0478(12) 0.0057(11) 0.0201(10) -0.0037(12)
C15 0.0481(14) 0.0606(16) 0.0621(14) -0.0038(12) 0.0210(11) -0.0164(12)
C16 0.0504(14) 0.0438(13) 0.0621(14) -0.0021(11) 0.0251(11) -0.0052(11)
C17 0.0412(14) 0.096(2) 0.0687(16) 0.0102(15) 0.0194(12) -0.0030(13)
O1 0.0639(11) 0.0363(9) 0.0865(12) 0.0107(8) 0.0255(9) -0.0065(8)
O3 0.0486(9) 0.0344(8) 0.0631(10) 0.0075(7) 0.0197(7) 0.0060(7)

_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
C1 O1 1.207(2) . ?
C1 O3 1.375(2) . ?
C1 C10 1.465(3) . ?
C3 O3 1.374(2) . ?
C3 C4 1.374(3) . ?
C3 C8 1.387(3) . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.393(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.426(3) . ?
C9 C10 1.348(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.482(3) . ?
C11 C12 1.388(3) . ?
C11 C16 1.396(3) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(3) . ?
C14 C17 1.505(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
O1 C1 O3 115.86(19) . . ?
O1 C1 C10 126.4(2) . . ?
O3 C1 C10 117.74(18) . . ?
O3 C3 C4 117.95(19) . . ?
O3 C3 C8 119.86(18) . . ?
C4 C3 C8 122.2(2) . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 119.7(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C3 C8 C7 117.71(18) . . ?
C3 C8 C9 117.82(18) . . ?
C7 C8 C9 124.46(18) . . ?
C10 C9 C8 123.27(18) . . ?
C10 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
C9 C10 C1 117.94(18) . . ?
C9 C10 C11 122.40(18) . . ?
C1 C10 C11 119.65(18) . . ?
C12 C11 C16 116.8(2) . . ?
C12 C11 C10 119.73(19) . . ?
C16 C11 C10 123.37(19) . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 121.9(2) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 117.0(2) . . ?
C13 C14 C17 121.5(2) . . ?
C15 C14 C17 121.6(2) . . ?
C16 C15 C14 122.0(2) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
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 . . ?
C3 O3 C1 123.23(16) . . ?

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
O3 C3 C4 C5 179.7(2) . . . . ?
C8 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
O3 C3 C8 C7 -178.44(18) . . . . ?
C4 C3 C8 C7 1.2(3) . . . . ?
O3 C3 C8 C9 2.7(3) . . . . ?
C4 C3 C8 C9 -177.65(18) . . . . ?
C6 C7 C8 C3 -1.3(3) . . . . ?
C6 C7 C8 C9 177.45(19) . . . . ?
C3 C8 C9 C10 -1.4(3) . . . . ?
C7 C8 C9 C10 179.86(19) . . . . ?
C8 C9 C10 C1 -1.9(3) . . . . ?
C8 C9 C10 C11 179.00(18) . . . . ?
O1 C1 C10 C9 -175.9(2) . . . . ?
O3 C1 C10 C9 3.9(3) . . . . ?
O1 C1 C10 C11 3.2(3) . . . . ?
O3 C1 C10 C11 -176.96(17) . . . . ?
C9 C10 C11 C12 25.0(3) . . . . ?
C1 C10 C11 C12 -154.0(2) . . . . ?
C9 C10 C11 C16 -151.7(2) . . . . ?
C1 C10 C11 C16 29.2(3) . . . . ?
C16 C11 C12 C13 -0.1(3) . . . . ?
C10 C11 C12 C13 -177.1(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C12 C13 C14 C17 -179.9(2) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C17 C14 C15 C16 179.8(2) . . . . ?
C14 C15 C16 C11 0.0(4) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
C10 C11 C16 C15 176.9(2) . . . . ?
C4 C3 O3 C1 179.75(19) . . . . ?
C8 C3 O3 C1 -0.6(3) . . . . ?
O1 C1 O3 C3 177.15(19) . . . . ?
C10 C1 O3 C3 -2.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 947235'
