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


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#                                CCDC 
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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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data_3a
_database_code_depnum_ccdc_archive 'CCDC 879659'
#TrackingRef '- 3a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H22 O'
_chemical_formula_sum            'C27 H22 O'
_chemical_formula_weight         362.45

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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           ?
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8927(7)
_cell_length_b                   11.1096(9)
_cell_length_c                   11.2148(7)
_cell_angle_alpha                64.309(7)
_cell_angle_beta                 75.677(6)
_cell_angle_gamma                87.598(7)
_cell_volume                     964.69(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       brick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384.0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_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            6725
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3395
_reflns_number_gt                2717
_reflns_threshold_expression     >2sigma(I)

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

_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^)+(0.1284P)^2^+1.7872P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3390
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.2089
_refine_ls_wR_factor_gt          0.1939
_refine_ls_goodness_of_fit_ref   0.780
_refine_ls_restrained_S_all      0.780
_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
C17 C 0.8100(4) -0.0329(3) 0.3183(4) 0.0666(10) Uani 1 1 d . . .
H17 H 0.8546 -0.1146 0.3466 0.080 Uiso 1 1 calc R . .
C16 C 0.7141(4) -0.0039(4) 0.2312(4) 0.0686(10) Uani 1 1 d . . .
H16 H 0.6939 -0.0654 0.2005 0.082 Uiso 1 1 calc R . .
C7 C 0.8330(3) 0.5233(3) 0.2054(3) 0.0368(6) Uani 1 1 d . . .
C13A C 0.8212(3) 0.2887(3) 0.3639(3) 0.0373(6) Uani 1 1 d . . .
C8 C 0.7335(3) 0.4152(3) 0.3119(3) 0.0379(6) Uani 1 1 d . . .
C3 C 0.9919(3) 0.4780(3) 0.1847(3) 0.0376(6) Uani 1 1 d . . .
C9 C 0.5746(3) 0.4301(3) 0.3538(3) 0.0427(6) Uani 1 1 d . . .
C20 C 0.8116(3) 0.2374(3) 0.5177(3) 0.0402(6) Uani 1 1 d . . .
C13 C 0.7742(3) 0.1820(3) 0.3240(3) 0.0395(6) Uani 1 1 d . . .
C10 C 0.5220(3) 0.5543(3) 0.2851(3) 0.0497(7) Uani 1 1 d . . .
H10 H 0.4170 0.5673 0.3103 0.060 Uiso 1 1 calc R . .
C2 C 0.9880(3) 0.3442(3) 0.2787(3) 0.0386(6) Uani 1 1 d . . .
C11 C 0.6218(4) 0.6602(3) 0.1795(3) 0.0469(7) Uani 1 1 d . . .
C12 C 0.7801(3) 0.6487(3) 0.1369(3) 0.0421(6) Uani 1 1 d . . .
O1 O 0.5624(3) 0.7813(2) 0.1130(3) 0.0675(7) Uani 1 1 d . . .
H1A H 0.6327 0.8345 0.0528 0.101 Uiso 1 1 calc R . .
C14 C 0.6782(3) 0.2089(3) 0.2362(3) 0.0462(7) Uani 1 1 d . . .
H14 H 0.6328 0.2902 0.2075 0.055 Uiso 1 1 calc R . .
C31 C 0.4614(3) 0.3183(3) 0.4672(3) 0.0548(8) Uani 1 1 d . . .
H31A H 0.5157 0.2394 0.5040 0.082 Uiso 1 1 calc R . .
H31B H 0.3822 0.2996 0.4315 0.082 Uiso 1 1 calc R . .
H31C H 0.4142 0.3446 0.5381 0.082 Uiso 1 1 calc R . .
C21 C 0.7321(3) 0.1179(3) 0.6196(3) 0.0498(7) Uani 1 1 d . . .
H21 H 0.6797 0.0639 0.5964 0.060 Uiso 1 1 calc R . .
C4 C 1.1340(3) 0.5438(3) 0.0948(3) 0.0497(7) Uani 1 1 d . . .
H4 H 1.1384 0.6324 0.0304 0.060 Uiso 1 1 calc R . .
C22 C 0.8846(4) 0.3166(3) 0.5576(3) 0.0507(7) Uani 1 1 d . . .
H22 H 0.9368 0.3979 0.4916 0.061 Uiso 1 1 calc R . .
C18 C 0.8403(4) 0.0584(3) 0.3637(3) 0.0540(8) Uani 1 1 d . . .
H18 H 0.9058 0.0375 0.4219 0.065 Uiso 1 1 calc R . .
C6 C 1.2633(4) 0.3458(4) 0.1972(3) 0.0599(9) Uani 1 1 d . . .
H6 H 1.3549 0.3023 0.2015 0.072 Uiso 1 1 calc R . .
C30 C 0.8837(4) 0.7671(3) 0.0233(3) 0.0558(8) Uani 1 1 d . . .
H30A H 0.9887 0.7421 0.0070 0.084 Uiso 1 1 calc R . .
H30B H 0.8797 0.8393 0.0491 0.084 Uiso 1 1 calc R . .
H30C H 0.8486 0.7954 -0.0585 0.084 Uiso 1 1 calc R . .
C28 C 0.7300(4) 0.0781(3) 0.7561(3) 0.0581(8) Uani 1 1 d . . .
H28 H 0.6772 -0.0026 0.8229 0.070 Uiso 1 1 calc R . .
C15 C 0.6487(4) 0.1170(4) 0.1906(3) 0.0594(9) Uani 1 1 d . . .
H15 H 0.5840 0.1373 0.1318 0.071 Uiso 1 1 calc R . .
C29 C 0.8049(4) 0.1566(4) 0.7928(3) 0.0601(9) Uani 1 1 d . . .
H29 H 0.8043 0.1290 0.8840 0.072 Uiso 1 1 calc R . .
C1 C 1.1232(3) 0.2783(3) 0.2866(3) 0.0511(7) Uani 1 1 d . . .
H1 H 1.1203 0.1899 0.3510 0.061 Uiso 1 1 calc R . .
C5 C 1.2671(4) 0.4764(4) 0.1024(3) 0.0594(8) Uani 1 1 d . . .
H5 H 1.3614 0.5201 0.0422 0.071 Uiso 1 1 calc R . .
C27 C 0.8812(4) 0.2771(4) 0.6935(3) 0.0592(8) Uani 1 1 d . . .
H27 H 0.9305 0.3319 0.7179 0.071 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
C17 0.069(2) 0.0474(18) 0.084(2) -0.0355(18) -0.0075(19) 0.0045(16)
C16 0.072(2) 0.065(2) 0.077(2) -0.0473(19) -0.0004(19) -0.0144(18)
C7 0.0400(14) 0.0404(14) 0.0369(13) -0.0216(11) -0.0129(11) 0.0039(11)
C13A 0.0358(13) 0.0398(14) 0.0374(13) -0.0172(11) -0.0110(11) 0.0029(11)
C8 0.0371(14) 0.0441(14) 0.0386(13) -0.0223(12) -0.0120(11) 0.0034(11)
C3 0.0359(13) 0.0453(14) 0.0366(13) -0.0218(11) -0.0103(11) 0.0017(11)
C9 0.0377(14) 0.0519(16) 0.0455(15) -0.0281(13) -0.0100(12) 0.0055(12)
C20 0.0385(14) 0.0440(15) 0.0395(14) -0.0187(12) -0.0123(11) 0.0087(11)
C13 0.0363(13) 0.0421(14) 0.0378(13) -0.0169(11) -0.0059(11) -0.0006(11)
C10 0.0383(15) 0.0597(18) 0.0598(18) -0.0341(15) -0.0142(13) 0.0136(13)
C2 0.0356(13) 0.0455(15) 0.0392(13) -0.0215(12) -0.0115(11) 0.0046(11)
C11 0.0520(17) 0.0445(15) 0.0547(17) -0.0276(13) -0.0222(14) 0.0153(13)
C12 0.0483(16) 0.0419(15) 0.0429(14) -0.0227(12) -0.0160(12) 0.0065(12)
O1 0.0688(15) 0.0507(13) 0.0779(16) -0.0222(12) -0.0244(12) 0.0222(11)
C14 0.0431(15) 0.0522(16) 0.0439(15) -0.0222(13) -0.0090(12) -0.0015(12)
C31 0.0394(15) 0.066(2) 0.0552(18) -0.0268(15) -0.0040(13) 0.0012(14)
C21 0.0467(16) 0.0528(17) 0.0459(16) -0.0168(13) -0.0134(13) -0.0008(13)
C4 0.0442(16) 0.0545(17) 0.0451(16) -0.0192(13) -0.0062(12) -0.0027(13)
C22 0.0589(18) 0.0488(16) 0.0479(16) -0.0234(14) -0.0150(14) 0.0015(14)
C18 0.0544(18) 0.0478(17) 0.0632(19) -0.0258(15) -0.0183(15) 0.0079(14)
C6 0.0373(16) 0.078(2) 0.066(2) -0.0319(18) -0.0165(14) 0.0133(15)
C30 0.063(2) 0.0449(16) 0.0529(18) -0.0143(14) -0.0168(15) 0.0067(14)
C28 0.0503(17) 0.065(2) 0.0424(16) -0.0096(15) -0.0097(13) 0.0054(15)
C15 0.0558(19) 0.075(2) 0.0565(18) -0.0376(17) -0.0110(15) -0.0112(16)
C29 0.0571(19) 0.086(2) 0.0382(16) -0.0269(16) -0.0161(14) 0.0159(17)
C1 0.0405(15) 0.0580(18) 0.0545(17) -0.0230(14) -0.0160(13) 0.0106(13)
C5 0.0377(16) 0.078(2) 0.0592(19) -0.0305(18) -0.0039(14) -0.0024(15)
C27 0.068(2) 0.070(2) 0.0531(18) -0.0371(17) -0.0209(16) 0.0081(17)

_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
C17 C18 1.378(5) . ?
C17 C16 1.379(5) . ?
C16 C15 1.372(5) . ?
C7 C12 1.397(4) . ?
C7 C8 1.405(4) . ?
C7 C3 1.477(4) . ?
C13A C8 1.532(4) . ?
C13A C2 1.535(4) . ?
C13A C13 1.540(4) . ?
C13A C20 1.545(4) . ?
C8 C9 1.401(4) . ?
C3 C2 1.396(4) . ?
C3 C4 1.398(4) . ?
C9 C10 1.386(4) . ?
C9 C31 1.509(4) . ?
C20 C21 1.390(4) . ?
C20 C22 1.389(4) . ?
C13 C14 1.388(4) . ?
C13 C18 1.400(4) . ?
C10 C11 1.391(4) . ?
C2 C1 1.383(4) . ?
C11 O1 1.382(3) . ?
C11 C12 1.389(4) . ?
C12 C30 1.507(4) . ?
C14 C15 1.384(4) . ?
C21 C28 1.392(4) . ?
C4 C5 1.374(4) . ?
C22 C27 1.384(4) . ?
C6 C5 1.374(5) . ?
C6 C1 1.388(4) . ?
C28 C29 1.367(5) . ?
C29 C27 1.379(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
C18 C17 C16 120.5(3) . . ?
C15 C16 C17 119.2(3) . . ?
C12 C7 C8 122.4(2) . . ?
C12 C7 C3 129.4(2) . . ?
C8 C7 C3 108.2(2) . . ?
C8 C13A C2 100.6(2) . . ?
C8 C13A C13 112.2(2) . . ?
C2 C13A C13 107.3(2) . . ?
C8 C13A C20 111.1(2) . . ?
C2 C13A C20 110.0(2) . . ?
C13 C13A C20 114.6(2) . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 C13A 128.2(2) . . ?
C7 C8 C13A 111.2(2) . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 C7 108.5(2) . . ?
C4 C3 C7 132.3(3) . . ?
C10 C9 C8 117.1(3) . . ?
C10 C9 C31 119.7(3) . . ?
C8 C9 C31 123.2(3) . . ?
C21 C20 C22 117.6(3) . . ?
C21 C20 C13A 124.3(2) . . ?
C22 C20 C13A 118.1(2) . . ?
C14 C13 C18 117.1(3) . . ?
C14 C13 C13A 121.7(2) . . ?
C18 C13 C13A 120.8(2) . . ?
C9 C10 C11 121.8(3) . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 C13A 128.0(2) . . ?
C3 C2 C13A 111.2(2) . . ?
O1 C11 C12 118.3(3) . . ?
O1 C11 C10 119.3(3) . . ?
C12 C11 C10 122.4(3) . . ?
C11 C12 C7 115.9(3) . . ?
C11 C12 C30 120.3(3) . . ?
C7 C12 C30 123.8(3) . . ?
C15 C14 C13 121.3(3) . . ?
C20 C21 C28 120.8(3) . . ?
C5 C4 C3 119.4(3) . . ?
C27 C22 C20 121.3(3) . . ?
C17 C18 C13 121.3(3) . . ?
C5 C6 C1 120.2(3) . . ?
C29 C28 C21 120.6(3) . . ?
C16 C15 C14 120.6(3) . . ?
C28 C29 C27 119.4(3) . . ?
C2 C1 C6 119.2(3) . . ?
C6 C5 C4 121.2(3) . . ?
C29 C27 C22 120.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.050