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

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#
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#                                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.
#
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#  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_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 O3'
_chemical_formula_weight         314.32

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                   8.4034(2)
_cell_length_b                   6.9101(2)
_cell_length_c                   25.2649(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.6350(10)
_cell_angle_gamma                90.00
_cell_volume                     1466.49(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13399
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         28.13
_reflns_number_total             3568
_reflns_number_gt                3161
_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)+(0.0616P)²+0.5145P] 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_number_reflns         3568
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 1.01633(9) 0.83837(13) 0.07637(3) 0.0184(2) Uani 1 1 d . . .
O2 O 0.49623(10) 1.03206(13) 0.12277(3) 0.0227(2) Uani 1 1 d . . .
O3 O 0.62392(9) 0.58605(12) 0.11727(3) 0.01692(19) Uani 1 1 d . . .
C14 C 0.87025(15) 0.69087(18) -0.05363(5) 0.0209(3) Uani 1 1 d . . .
H14 H 0.9109 0.6610 -0.0865 0.025 Uiso 1 1 calc R . .
C13 C 0.97238(14) 0.74277(18) -0.01234(5) 0.0197(2) Uani 1 1 d . . .
H13 H 1.0811 0.7535 -0.0175 0.024 Uiso 1 1 calc R . .
C12 C 0.91009(13) 0.77901(17) 0.03742(4) 0.0158(2) Uani 1 1 d . . .
C11 C 0.95823(13) 0.89211(17) 0.12489(4) 0.0157(2) Uani 1 1 d . . .
C10 C 1.07462(14) 0.98257(18) 0.15805(5) 0.0192(2) Uani 1 1 d . . .
H10 H 1.1761 1.0063 0.1458 0.023 Uiso 1 1 calc R . .
C9 C 1.03661(14) 1.03436(18) 0.20797(5) 0.0201(2) Uani 1 1 d . . .
H9 H 1.1110 1.0997 0.2293 0.024 Uiso 1 1 calc R . .
C8 C 0.88467(14) 0.99010(17) 0.22813(5) 0.0183(2) Uani 1 1 d . . .
C7 C 0.84901(16) 1.03131(19) 0.28154(5) 0.0227(3) Uani 1 1 d . . .
H7 H 0.9230 1.0975 0.3028 0.027 Uiso 1 1 calc R . .
C6 C 0.70775(16) 0.9753(2) 0.30231(5) 0.0257(3) Uani 1 1 d . . .
H6 H 0.6856 1.0042 0.3373 0.031 Uiso 1 1 calc R . .
C15 C 0.70639(15) 0.68294(18) -0.04640(5) 0.0202(3) Uani 1 1 d . . .
H15 H 0.6379 0.6520 -0.0747 0.024 Uiso 1 1 calc R . .
C16 C 0.64556(13) 0.72127(17) 0.00299(4) 0.0172(2) Uani 1 1 d . . .
C17 C 0.74962(13) 0.76109(16) 0.04652(4) 0.0150(2) Uani 1 1 d . . .
C1 C 0.68311(12) 0.77516(16) 0.10147(4) 0.0145(2) Uani 1 1 d . . .
C2 C 0.80455(13) 0.85782(16) 0.14041(4) 0.0147(2) Uani 1 1 d . . .
C3 C 0.76854(13) 0.89684(17) 0.19483(4) 0.0161(2) Uani 1 1 d . . .
C5 C 0.59602(15) 0.8737(2) 0.27036(5) 0.0248(3) Uani 1 1 d . . .
H5 H 0.5019 0.8308 0.2849 0.030 Uiso 1 1 calc R . .
C4 C 0.62422(14) 0.83695(18) 0.21813(5) 0.0201(3) Uani 1 1 d . . .
H4 H 0.5479 0.7719 0.1976 0.024 Uiso 1 1 calc R . .
C20 C 0.52570(13) 0.89153(17) 0.09604(4) 0.0169(2) Uani 1 1 d . . .
C19 C 0.41527(14) 0.81941(19) 0.05385(5) 0.0208(3) Uani 1 1 d . . .
H19 H 0.3058 0.8299 0.0575 0.025 Uiso 1 1 calc R . .
C18 C 0.47389(14) 0.73915(18) 0.01048(5) 0.0203(3) Uani 1 1 d . . .
H18 H 0.4037 0.6932 -0.0157 0.024 Uiso 1 1 calc R . .
C21 C 0.74435(14) 0.44620(18) 0.12852(5) 0.0219(3) Uani 1 1 d . . .
H21A H 0.8175 0.4429 0.1000 0.033 Uiso 1 1 calc R . .
H21B H 0.6964 0.3211 0.1323 0.033 Uiso 1 1 calc R . .
H21C H 0.8005 0.4802 0.1608 0.033 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 C12 1.3725(13) . ?
O1 C11 1.3831(13) . ?
O2 C20 1.2123(15) . ?
O3 C21 1.4221(14) . ?
O3 C1 1.4580(13) . ?
C14 C13 1.3793(17) . ?
C14 C15 1.3953(17) . ?
C14 H14 0.9300 . ?
C13 C12 1.3981(16) . ?
C13 H13 0.9300 . ?
C12 C17 1.3799(15) . ?
C11 C2 1.3808(15) . ?
C11 C10 1.4150(16) . ?
C10 C9 1.3579(17) . ?
C10 H10 0.9300 . ?
C9 C8 1.4213(17) . ?
C9 H9 0.9300 . ?
C8 C7 1.4195(16) . ?
C8 C3 1.4243(16) . ?
C7 C6 1.3674(19) . ?
C7 H7 0.9300 . ?
C6 C5 1.4084(19) . ?
C6 H6 0.9300 . ?
C15 C16 1.3875(16) . ?
C15 H15 0.9300 . ?
C16 C17 1.4123(15) . ?
C16 C18 1.4656(16) . ?
C17 C1 1.5145(15) . ?
C1 C2 1.5095(15) . ?
C1 C20 1.5508(15) . ?
C2 C3 1.4417(15) . ?
C3 C4 1.4245(16) . ?
C5 C4 1.3709(17) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C20 C19 1.4797(16) . ?
C19 C18 1.3347(17) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C12 O1 C11 118.48(8) . . ?
C21 O3 C1 114.67(8) . . ?
C13 C14 C15 120.42(11) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C13 C12 119.07(11) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
O1 C12 C17 121.75(10) . . ?
O1 C12 C13 116.47(10) . . ?
C17 C12 C13 121.76(10) . . ?
C2 C11 O1 124.21(10) . . ?
C2 C11 C10 122.96(10) . . ?
O1 C11 C10 112.81(9) . . ?
C9 C10 C11 119.29(11) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C9 C8 120.91(11) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C7 C8 C9 120.91(11) . . ?
C7 C8 C3 119.51(11) . . ?
C9 C8 C3 119.54(11) . . ?
C6 C7 C8 121.14(12) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C6 C5 119.54(11) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C16 C15 C14 120.04(11) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.11(10) . . ?
C15 C16 C18 121.43(10) . . ?
C17 C16 C18 118.23(10) . . ?
C12 C17 C16 118.30(10) . . ?
C12 C17 C1 122.34(10) . . ?
C16 C17 C1 119.32(10) . . ?
O3 C1 C2 112.97(9) . . ?
O3 C1 C17 109.34(9) . . ?
C2 C1 C17 111.19(9) . . ?
O3 C1 C20 101.08(8) . . ?
C2 C1 C20 114.86(9) . . ?
C17 C1 C20 106.77(9) . . ?
C11 C2 C3 117.53(10) . . ?
C11 C2 C1 120.02(10) . . ?
C3 C2 C1 122.41(9) . . ?
C8 C3 C4 117.68(10) . . ?
C8 C3 C2 119.28(10) . . ?
C4 C3 C2 122.96(10) . . ?
C4 C5 C6 120.88(12) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 121.10(11) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
O2 C20 C19 122.49(11) . . ?
O2 C20 C1 123.60(10) . . ?
C19 C20 C1 113.88(10) . . ?
C18 C19 C20 119.52(10) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C18 C16 121.92(11) . . ?
C19 C18 H18 119.0 . . ?
C16 C18 H18 119.0 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C15 C14 C13 C12 2.78(18) . . . . ?
C11 O1 C12 C17 -3.87(16) . . . . ?
C11 O1 C12 C13 174.45(10) . . . . ?
C14 C13 C12 O1 -177.21(11) . . . . ?
C14 C13 C12 C17 1.10(18) . . . . ?
C12 O1 C11 C2 12.25(17) . . . . ?
C12 O1 C11 C10 -169.29(10) . . . . ?
C2 C11 C10 C9 1.76(18) . . . . ?
O1 C11 C10 C9 -176.72(10) . . . . ?
C11 C10 C9 C8 3.24(18) . . . . ?
C10 C9 C8 C7 175.28(11) . . . . ?
C10 C9 C8 C3 -2.46(18) . . . . ?
C9 C8 C7 C6 -174.79(12) . . . . ?
C3 C8 C7 C6 2.96(19) . . . . ?
C8 C7 C6 C5 0.5(2) . . . . ?
C13 C14 C15 C16 -2.10(19) . . . . ?
C14 C15 C16 C17 -2.42(18) . . . . ?
C14 C15 C16 C18 171.92(11) . . . . ?
O1 C12 C17 C16 172.72(10) . . . . ?
C13 C12 C17 C16 -5.50(17) . . . . ?
O1 C12 C17 C1 -9.62(17) . . . . ?
C13 C12 C17 C1 172.15(11) . . . . ?
C15 C16 C17 C12 6.13(17) . . . . ?
C18 C16 C17 C12 -168.39(11) . . . . ?
C15 C16 C17 C1 -171.61(11) . . . . ?
C18 C16 C17 C1 13.88(16) . . . . ?
C21 O3 C1 C2 -53.30(12) . . . . ?
C21 O3 C1 C17 71.10(11) . . . . ?
C21 O3 C1 C20 -176.55(9) . . . . ?
C12 C17 C1 O3 -111.45(12) . . . . ?
C16 C17 C1 O3 66.19(13) . . . . ?
C12 C17 C1 C2 13.98(15) . . . . ?
C16 C17 C1 C2 -168.38(10) . . . . ?
C12 C17 C1 C20 139.98(11) . . . . ?
C16 C17 C1 C20 -42.38(14) . . . . ?
O1 C11 C2 C3 171.14(10) . . . . ?
C10 C11 C2 C3 -7.18(17) . . . . ?
O1 C11 C2 C1 -6.55(17) . . . . ?
C10 C11 C2 C1 175.13(11) . . . . ?
O3 C1 C2 C11 117.29(11) . . . . ?
C17 C1 C2 C11 -6.09(15) . . . . ?
C20 C1 C2 C11 -127.47(11) . . . . ?
O3 C1 C2 C3 -60.29(14) . . . . ?
C17 C1 C2 C3 176.33(10) . . . . ?
C20 C1 C2 C3 54.96(14) . . . . ?
C7 C8 C3 C4 -4.20(17) . . . . ?
C9 C8 C3 C4 173.58(11) . . . . ?
C7 C8 C3 C2 179.12(11) . . . . ?
C9 C8 C3 C2 -3.10(17) . . . . ?
C11 C2 C3 C8 7.69(16) . . . . ?
C1 C2 C3 C8 -174.68(10) . . . . ?
C11 C2 C3 C4 -168.81(11) . . . . ?
C1 C2 C3 C4 8.82(17) . . . . ?
C7 C6 C5 C4 -2.7(2) . . . . ?
C6 C5 C4 C3 1.3(2) . . . . ?
C8 C3 C4 C5 2.13(18) . . . . ?
C2 C3 C4 C5 178.68(11) . . . . ?
O3 C1 C20 O2 117.89(12) . . . . ?
C2 C1 C20 O2 -4.05(16) . . . . ?
C17 C1 C20 O2 -127.81(12) . . . . ?
O3 C1 C20 C19 -63.94(11) . . . . ?
C2 C1 C20 C19 174.12(9) . . . . ?
C17 C1 C20 C19 50.36(12) . . . . ?
O2 C20 C19 C18 146.40(13) . . . . ?
C1 C20 C19 C18 -31.79(16) . . . . ?
C20 C19 C18 C16 -0.50(19) . . . . ?
C15 C16 C18 C19 -163.94(12) . . . . ?
C17 C16 C18 C19 10.51(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.13
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.060
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_database_code_depnum_ccdc_archive 'CCDC 1015210'
