# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_acs_68
_database_code_depnum_ccdc_archive 'CCDC 1045946'
_audit_update_record             
;
2015-01-28 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 O5'
_chemical_formula_sum            'C24 H24 O5'
_chemical_formula_weight         392.43

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                   7.9447(10)
_cell_length_b                   19.588(2)
_cell_length_c                   12.7483(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.927(5)
_cell_angle_gamma                90.00
_cell_volume                     1964.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5593
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.87

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9518
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_process_details   'Bruker 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            18612
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         28.33
_reflns_number_total             4865
_reflns_number_gt                3453
_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)+(0.0491P)²+0.2502P] 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       0.0055(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4865
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.50813(17) 0.47654(7) 0.74609(10) 0.0371(3) Uani 1 1 d . . .
C2 C 0.38984(17) 0.45371(7) 0.65892(10) 0.0354(3) Uani 1 1 d . . .
C3 C 0.32992(17) 0.38737(7) 0.66289(10) 0.0371(3) Uani 1 1 d . . .
H3 H 0.2505 0.3719 0.6076 0.045 Uiso 1 1 calc R . .
C4 C 0.38327(17) 0.34331(7) 0.74569(10) 0.0362(3) Uani 1 1 d . . .
C5 C 0.50677(17) 0.36662(7) 0.82760(9) 0.0354(3) Uani 1 1 d . . .
C6 C 0.56703(18) 0.43210(7) 0.82753(10) 0.0394(3) Uani 1 1 d . . .
H6 H 0.6481 0.4469 0.8825 0.047 Uiso 1 1 calc R . .
C7 C 0.30739(19) 0.27543(7) 0.75301(12) 0.0443(4) Uani 1 1 d . . .
C8 C 0.3624(2) 0.23849(8) 0.85625(12) 0.0459(4) Uani 1 1 d . . .
H8A H 0.3466 0.1898 0.8454 0.055 Uiso 1 1 calc R . .
H8B H 0.2914 0.2529 0.9082 0.055 Uiso 1 1 calc R . .
C9 C 0.54709(18) 0.25258(6) 0.89853(10) 0.0373(3) Uani 1 1 d . . .
O10 O 0.56965(13) 0.32672(5) 0.91038(7) 0.0419(3) Uani 1 1 d . . .
C11 C 0.66664(18) 0.22628(7) 0.82397(10) 0.0385(3) Uani 1 1 d . . .
H11A H 0.6481 0.1777 0.8132 0.046 Uiso 1 1 calc R . .
H11B H 0.6394 0.2486 0.7558 0.046 Uiso 1 1 calc R . .
C12 C 0.8528(2) 0.23849(8) 0.86521(12) 0.0476(4) Uani 1 1 d . . .
H12A H 0.8753 0.2872 0.8688 0.057 Uiso 1 1 calc R . .
H12B H 0.9231 0.2184 0.8169 0.057 Uiso 1 1 calc R . .
C13 C 0.8981(2) 0.20725(9) 0.97455(12) 0.0531(4) Uani 1 1 d . . .
H13A H 0.8857 0.1580 0.9697 0.064 Uiso 1 1 calc R . .
H13B H 1.0158 0.2174 1.0011 0.064 Uiso 1 1 calc R . .
C14 C 0.7843(2) 0.23501(9) 1.05093(11) 0.0529(4) Uani 1 1 d . . .
H14A H 0.8065 0.2834 1.0619 0.064 Uiso 1 1 calc R . .
H14B H 0.8112 0.2122 1.1187 0.064 Uiso 1 1 calc R . .
C15 C 0.5969(2) 0.22459(8) 1.00975(10) 0.0461(4) Uani 1 1 d . . .
H15A H 0.5713 0.1762 1.0098 0.055 Uiso 1 1 calc R . .
H15B H 0.5290 0.2469 1.0574 0.055 Uiso 1 1 calc R . .
O16 O 0.20558(17) 0.25123(6) 0.68335(10) 0.0712(4) Uani 1 1 d . . .
O17 O 0.56701(14) 0.54043(5) 0.75193(8) 0.0503(3) Uani 1 1 d . . .
H17 H 0.5306 0.5610 0.6975 0.075 Uiso 1 1 calc R . .
C18 C 0.33633(17) 0.50085(7) 0.57110(10) 0.0378(3) Uani 1 1 d . . .
C19 C 0.21503(18) 0.47945(8) 0.47968(11) 0.0426(3) Uani 1 1 d . . .
H19 H 0.1694 0.4357 0.4778 0.051 Uiso 1 1 calc R . .
O20 O 0.39625(14) 0.55952(5) 0.57310(8) 0.0504(3) Uani 1 1 d . . .
C21 C 0.16967(18) 0.52206(8) 0.39940(11) 0.0415(3) Uani 1 1 d . . .
H21 H 0.2189 0.5652 0.4055 0.050 Uiso 1 1 calc R . .
C22 C 0.05205(17) 0.50931(7) 0.30297(10) 0.0388(3) Uani 1 1 d . . .
C23 C -0.0244(2) 0.44628(8) 0.27973(12) 0.0494(4) Uani 1 1 d . . .
H23 H -0.0006 0.4099 0.3263 0.059 Uiso 1 1 calc R . .
C24 C -0.1349(2) 0.43768(8) 0.18805(13) 0.0558(4) Uani 1 1 d . . .
H24 H -0.1866 0.3955 0.1735 0.067 Uiso 1 1 calc R . .
C25 C -0.1709(2) 0.49094(8) 0.11660(12) 0.0513(4) Uani 1 1 d . . .
H25 H -0.2458 0.4844 0.0546 0.062 Uiso 1 1 calc R . .
C26 C -0.09479(19) 0.55340(7) 0.13816(11) 0.0434(3) Uani 1 1 d . . .
C27 C 0.01574(19) 0.56249(7) 0.23143(10) 0.0413(3) Uani 1 1 d . . .
H27 H 0.0662 0.6049 0.2462 0.050 Uiso 1 1 calc R . .
C28 C -0.2200(2) 0.60121(10) -0.02699(12) 0.0651(5) Uani 1 1 d . . .
H28A H -0.1738 0.5647 -0.0644 0.098 Uiso 1 1 calc R . .
H28B H -0.2177 0.6428 -0.0667 0.098 Uiso 1 1 calc R . .
H28C H -0.3351 0.5906 -0.0181 0.098 Uiso 1 1 calc R . .
O29 O -0.12062(16) 0.60946(6) 0.07462(8) 0.0617(3) Uani 1 1 d . . .


_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 O17 1.3344(16) . ?
C1 C6 1.3858(18) . ?
C1 C2 1.4248(17) . ?
C2 C3 1.3871(19) . ?
C2 C18 1.4682(18) . ?
C3 C4 1.3839(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.4068(17) . ?
C4 C7 1.468(2) . ?
C5 O10 1.3523(15) . ?
C5 C6 1.3691(19) . ?
C6 H6 0.9300 . ?
C7 O16 1.2122(17) . ?
C7 C8 1.513(2) . ?
C8 C9 1.517(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O10 1.4685(16) . ?
C9 C15 1.5209(17) . ?
C9 C11 1.5232(19) . ?
C11 C12 1.519(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.519(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.518(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.523(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O17 H17 0.8200 . ?
C18 O20 1.2429(17) . ?
C18 C19 1.4672(19) . ?
C19 C21 1.3313(19) . ?
C19 H19 0.9300 . ?
C21 C22 1.4595(18) . ?
C21 H21 0.9300 . ?
C22 C27 1.3884(18) . ?
C22 C23 1.390(2) . ?
C23 C24 1.372(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.389(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(2) . ?
C25 H25 0.9300 . ?
C26 O29 1.3632(17) . ?
C26 C27 1.3887(19) . ?
C27 H27 0.9300 . ?
C28 O29 1.4301(18) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
O17 C1 C6 117.89(12) . . ?
O17 C1 C2 121.75(12) . . ?
C6 C1 C2 120.36(12) . . ?
C3 C2 C1 117.28(11) . . ?
C3 C2 C18 123.52(12) . . ?
C1 C2 C18 119.20(12) . . ?
C4 C3 C2 122.78(12) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C5 118.20(12) . . ?
C3 C4 C7 121.87(12) . . ?
C5 C4 C7 119.82(12) . . ?
O10 C5 C6 116.77(11) . . ?
O10 C5 C4 122.44(12) . . ?
C6 C5 C4 120.78(11) . . ?
C5 C6 C1 120.46(12) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O16 C7 C4 123.09(13) . . ?
O16 C7 C8 122.27(14) . . ?
C4 C7 C8 114.62(12) . . ?
C7 C8 C9 111.81(12) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
O10 C9 C8 108.35(11) . . ?
O10 C9 C15 104.38(10) . . ?
C8 C9 C15 112.34(12) . . ?
O10 C9 C11 108.72(11) . . ?
C8 C9 C11 111.87(11) . . ?
C15 C9 C11 110.82(11) . . ?
C5 O10 C9 117.68(10) . . ?
C12 C11 C9 113.08(11) . . ?
C12 C11 H11A 109.0 . . ?
C9 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C9 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 110.49(13) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 110.96(13) . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 111.79(12) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C9 C15 C14 112.91(13) . . ?
C9 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C9 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C1 O17 H17 109.5 . . ?
O20 C18 C19 119.22(12) . . ?
O20 C18 C2 119.74(12) . . ?
C19 C18 C2 121.03(12) . . ?
C21 C19 C18 120.66(14) . . ?
C21 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C21 C22 127.89(14) . . ?
C19 C21 H21 116.1 . . ?
C22 C21 H21 116.1 . . ?
C27 C22 C23 118.78(13) . . ?
C27 C22 C21 118.41(13) . . ?
C23 C22 C21 122.81(12) . . ?
C24 C23 C22 120.01(13) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 121.08(15) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 119.48(14) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
O29 C26 C25 124.87(13) . . ?
O29 C26 C27 115.53(13) . . ?
C25 C26 C27 119.59(13) . . ?
C22 C27 C26 121.05(13) . . ?
C22 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
O29 C28 H28A 109.5 . . ?
O29 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O29 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 O29 C28 117.79(13) . . ?

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
O17 C1 C2 C3 -176.85(13) . . . . ?
C6 C1 C2 C3 3.8(2) . . . . ?
O17 C1 C2 C18 2.5(2) . . . . ?
C6 C1 C2 C18 -176.86(13) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
C18 C2 C3 C4 179.19(13) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
C2 C3 C4 C7 174.53(13) . . . . ?
C3 C4 C5 O10 -178.36(12) . . . . ?
C7 C4 C5 O10 5.3(2) . . . . ?
C3 C4 C5 C6 2.7(2) . . . . ?
C7 C4 C5 C6 -173.55(13) . . . . ?
O10 C5 C6 C1 -179.43(12) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
O17 C1 C6 C5 177.78(13) . . . . ?
C2 C1 C6 C5 -2.9(2) . . . . ?
C3 C4 C7 O16 6.9(2) . . . . ?
C5 C4 C7 O16 -176.93(15) . . . . ?
C3 C4 C7 C8 -171.38(13) . . . . ?
C5 C4 C7 C8 4.8(2) . . . . ?
O16 C7 C8 C9 145.65(16) . . . . ?
C4 C7 C8 C9 -36.05(18) . . . . ?
C7 C8 C9 O10 56.69(15) . . . . ?
C7 C8 C9 C15 171.47(12) . . . . ?
C7 C8 C9 C11 -63.14(15) . . . . ?
C6 C5 O10 C9 -162.70(12) . . . . ?
C4 C5 O10 C9 18.36(19) . . . . ?
C8 C9 O10 C5 -48.81(15) . . . . ?
C15 C9 O10 C5 -168.72(12) . . . . ?
C11 C9 O10 C5 72.97(14) . . . . ?
O10 C9 C11 C12 61.45(14) . . . . ?
C8 C9 C11 C12 -178.93(11) . . . . ?
C15 C9 C11 C12 -52.71(16) . . . . ?
C9 C11 C12 C13 55.79(16) . . . . ?
C11 C12 C13 C14 -56.38(18) . . . . ?
C12 C13 C14 C15 55.48(18) . . . . ?
O10 C9 C15 C14 -65.90(15) . . . . ?
C8 C9 C15 C14 176.93(12) . . . . ?
C11 C9 C15 C14 50.97(16) . . . . ?
C13 C14 C15 C9 -53.22(17) . . . . ?
C3 C2 C18 O20 -179.76(13) . . . . ?
C1 C2 C18 O20 1.0(2) . . . . ?
C3 C2 C18 C19 -0.8(2) . . . . ?
C1 C2 C18 C19 179.89(12) . . . . ?
O20 C18 C19 C21 0.2(2) . . . . ?
C2 C18 C19 C21 -178.68(13) . . . . ?
C18 C19 C21 C22 179.82(13) . . . . ?
C19 C21 C22 C27 176.63(15) . . . . ?
C19 C21 C22 C23 -3.6(2) . . . . ?
C27 C22 C23 C24 -0.7(2) . . . . ?
C21 C22 C23 C24 179.51(15) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
C23 C24 C25 C26 -0.1(3) . . . . ?
C24 C25 C26 O29 -179.64(15) . . . . ?
C24 C25 C26 C27 -0.6(2) . . . . ?
C23 C22 C27 C26 0.0(2) . . . . ?
C21 C22 C27 C26 179.81(13) . . . . ?
O29 C26 C27 C22 179.78(13) . . . . ?
C25 C26 C27 C22 0.6(2) . . . . ?
C25 C26 O29 C28 -6.9(2) . . . . ?
C27 C26 O29 C28 174.02(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.037
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
