# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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:
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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_sad

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 O2'
_chemical_formula_weight         338.38

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   P21/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                   11.264(2)
_cell_length_b                   7.0576(14)
_cell_length_c                   22.435(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.75(3)
_cell_angle_gamma                90.00
_cell_volume                     1779.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plane
_exptl_crystal_colour            0colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_process_details   'SDABS (Sheldrick, 1997)'

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16740
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4058
_reflns_number_gt                1848
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SHELXL-97 (Sheldrick, 1997)'
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1043P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4058
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.2021
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 -0.17680(16) 0.1794(4) 0.08419(10) 0.0873(7) Uani 1 1 d . . .
O2 O 0.23483(15) 0.3142(3) 0.21351(7) 0.0694(6) Uani 1 1 d . . .
C1 C -0.00516(19) 0.0628(4) 0.13640(10) 0.0536(7) Uani 1 1 d . . .
C2 C -0.0651(2) -0.0603(4) 0.17269(12) 0.0624(8) Uani 1 1 d . . .
H2A H -0.1469 -0.0479 0.1748 0.075 Uiso 1 1 calc R . .
C3 C -0.0058(2) -0.1993(5) 0.20532(12) 0.0654(8) Uani 1 1 d . . .
H3A H -0.0465 -0.2773 0.2304 0.078 Uiso 1 1 calc R . .
C4 C 0.1139(2) -0.2224(5) 0.20066(12) 0.0664(8) Uani 1 1 d . . .
H4A H 0.1542 -0.3181 0.2221 0.080 Uiso 1 1 calc R . .
C5 C 0.1749(2) -0.1054(4) 0.16448(11) 0.0600(7) Uani 1 1 d . . .
H5A H 0.2559 -0.1248 0.1612 0.072 Uiso 1 1 calc R . .
C6 C 0.11808(19) 0.0417(4) 0.13268(10) 0.0522(6) Uani 1 1 d . . .
C7 C -0.0771(2) 0.2143(4) 0.10529(11) 0.0610(7) Uani 1 1 d . . .
C8 C -0.0327(3) 0.4115(6) 0.10393(16) 0.0965(11) Uiso 1 1 d . . .
H8A H -0.0900 0.4897 0.0820 0.145 Uiso 1 1 calc R . .
H8B H 0.0412 0.4144 0.0849 0.145 Uiso 1 1 calc R . .
H8C H -0.0203 0.4584 0.1440 0.145 Uiso 1 1 calc R . .
C9 C 0.18441(19) 0.1592(4) 0.09092(10) 0.0517(7) Uani 1 1 d . . .
C10 C 0.1625(2) 0.1317(4) 0.03015(11) 0.0606(7) Uani 1 1 d . . .
H10A H 0.1072 0.0410 0.0167 0.073 Uiso 1 1 calc R . .
C11 C 0.2207(2) 0.2356(5) -0.01084(11) 0.0655(8) Uani 1 1 d . . .
H11A H 0.2066 0.2115 -0.0514 0.079 Uiso 1 1 calc R . .
C12 C 0.2991(2) 0.3741(4) 0.00795(11) 0.0611(7) Uani 1 1 d . . .
H12A H 0.3351 0.4476 -0.0202 0.073 Uiso 1 1 calc R . .
C13 C 0.32629(19) 0.4073(4) 0.06877(10) 0.0511(6) Uani 1 1 d . . .
C14 C 0.27075(18) 0.2944(4) 0.11041(10) 0.0489(6) Uani 1 1 d . . .
C15 C 0.3070(2) 0.3108(4) 0.17518(10) 0.0524(6) Uani 1 1 d . . .
C16 C 0.4348(2) 0.2951(4) 0.19126(10) 0.0574(7) Uani 1 1 d . . .
H16A H 0.4580 0.1997 0.2181 0.069 Uiso 1 1 calc R . .
C17 C 0.5215(2) 0.4027(4) 0.17154(10) 0.0572(7) Uani 1 1 d . . .
C18 C 0.4961(2) 0.5672(4) 0.13158(11) 0.0552(7) Uani 1 1 d . . .
C19 C 0.40463(19) 0.5707(4) 0.08617(10) 0.0525(6) Uani 1 1 d . . .
C20 C 0.3846(2) 0.7370(4) 0.05338(12) 0.0648(8) Uani 1 1 d . . .
H20A H 0.3239 0.7399 0.0232 0.078 Uiso 1 1 calc R . .
C21 C 0.4524(3) 0.8968(5) 0.06450(14) 0.0770(9) Uani 1 1 d . . .
H21A H 0.4355 1.0077 0.0432 0.092 Uiso 1 1 calc R . .
C22 C 0.5457(3) 0.8914(5) 0.10748(15) 0.0796(10) Uani 1 1 d . . .
H22A H 0.5938 0.9973 0.1144 0.096 Uiso 1 1 calc R . .
C23 C 0.5671(2) 0.7291(5) 0.13990(13) 0.0706(9) Uani 1 1 d . . .
H23A H 0.6309 0.7263 0.1684 0.085 Uiso 1 1 calc R . .
C24 C 0.6477(2) 0.3656(6) 0.19361(13) 0.0818(10) Uani 1 1 d . . .
H24A H 0.6507 0.2558 0.2190 0.123 Uiso 1 1 calc R . .
H24B H 0.6783 0.4732 0.2158 0.123 Uiso 1 1 calc R . .
H24C H 0.6950 0.3438 0.1602 0.123 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 C7 1.215(3) . ?
O2 C15 1.222(3) . ?
C1 C2 1.395(4) . ?
C1 C6 1.404(3) . ?
C1 C7 1.488(4) . ?
C2 C3 1.371(4) . ?
C3 C4 1.369(4) . ?
C4 C5 1.373(4) . ?
C5 C6 1.392(4) . ?
C6 C9 1.488(3) . ?
C7 C8 1.480(5) . ?
C9 C10 1.383(3) . ?
C9 C14 1.412(4) . ?
C10 C11 1.375(4) . ?
C11 C12 1.365(4) . ?
C12 C13 1.399(3) . ?
C13 C14 1.405(3) . ?
C13 C19 1.489(4) . ?
C14 C15 1.488(3) . ?
C15 C16 1.465(3) . ?
C16 C17 1.336(4) . ?
C17 C18 1.483(4) . ?
C17 C24 1.498(4) . ?
C18 C23 1.400(4) . ?
C18 C19 1.401(3) . ?
C19 C20 1.396(4) . ?
C20 C21 1.375(4) . ?
C21 C22 1.380(5) . ?
C22 C23 1.370(5) . ?

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 119.1(3) . . ?
C2 C1 C7 116.9(2) . . ?
C6 C1 C7 124.0(2) . . ?
C3 C2 C1 121.3(2) . . ?
C4 C3 C2 119.5(3) . . ?
C3 C4 C5 120.4(3) . . ?
C4 C5 C6 121.4(2) . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 C9 120.3(2) . . ?
C1 C6 C9 121.2(2) . . ?
O1 C7 C8 119.2(3) . . ?
O1 C7 C1 119.9(3) . . ?
C8 C7 C1 120.7(2) . . ?
C10 C9 C14 118.3(2) . . ?
C10 C9 C6 118.6(2) . . ?
C14 C9 C6 123.1(2) . . ?
C11 C10 C9 121.5(3) . . ?
C12 C11 C10 120.1(2) . . ?
C11 C12 C13 121.1(2) . . ?
C12 C13 C14 118.4(2) . . ?
C12 C13 C19 118.3(2) . . ?
C14 C13 C19 123.1(2) . . ?
C13 C14 C9 120.3(2) . . ?
C13 C14 C15 120.0(2) . . ?
C9 C14 C15 119.6(2) . . ?
O2 C15 C16 121.1(2) . . ?
O2 C15 C14 122.4(2) . . ?
C16 C15 C14 115.9(2) . . ?
C17 C16 C15 127.1(3) . . ?
C16 C17 C18 121.9(2) . . ?
C16 C17 C24 119.3(3) . . ?
C18 C17 C24 118.6(2) . . ?
C23 C18 C19 118.0(3) . . ?
C23 C18 C17 118.2(2) . . ?
C19 C18 C17 123.9(2) . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 C13 116.2(2) . . ?
C18 C19 C13 124.9(2) . . ?
C21 C20 C19 121.7(3) . . ?
C20 C21 C22 119.5(3) . . ?
C23 C22 C21 119.6(3) . . ?
C22 C23 C18 122.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 998466'
