# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_akb_zd_0m
_database_code_depnum_ccdc_archive 'CCDC 1525170'
_audit_update_record             
;
2017-01-02 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 O5'
_chemical_formula_weight         340.36

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   9.5902(5)
_cell_length_b                   11.1506(5)
_cell_length_c                   14.3205(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1531.38(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9204
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         24.45
_reflns_number_total             2519
_reflns_number_gt                2224
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0363P)²+0.1235P] 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       0.0178(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(12)
_refine_ls_number_reflns         2519
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 -0.18470(15) 0.96883(14) 0.61687(10) 0.0751(4) Uani 1 1 d . . .
O2 O -0.00154(13) 0.98849(11) 0.71171(8) 0.0516(3) Uani 1 1 d . . .
O3 O 0.07819(15) 1.17012(11) 1.06288(10) 0.0632(4) Uani 1 1 d . . .
O4 O 0.1334(2) 1.26465(16) 1.19476(11) 0.0929(6) Uani 1 1 d . . .
C1 C -0.0620(2) 0.96269(17) 0.63024(13) 0.0505(5) Uani 1 1 d . . .
C2 C -0.09232(19) 1.03184(18) 0.78598(12) 0.0493(5) Uani 1 1 d . . .
H2 H -0.1566 1.0924 0.7614 0.059 Uiso 1 1 calc R . .
C3 C -0.0004(2) 1.08649(15) 0.86002(12) 0.0468(4) Uani 1 1 d . . .
C4 C -0.05201(18) 1.04543(15) 0.95438(12) 0.0439(4) Uani 1 1 d . . .
H4 H -0.1295 1.0974 0.9731 0.053 Uiso 1 1 calc R . .
C5 C 0.05574(19) 1.04671(15) 1.03113(12) 0.0455(4) Uani 1 1 d . . .
H5 H 0.1437 1.0166 1.0054 0.055 Uiso 1 1 calc R . .
C6 C 0.1009(2) 1.1728(2) 1.15623(15) 0.0647(6) Uani 1 1 d . . .
C7 C 0.0429(2) 0.9263(2) 0.55903(15) 0.0689(6) Uani 1 1 d . . .
H7A H -0.0040 0.8951 0.5050 0.103 Uiso 1 1 calc R . .
H7B H 0.1027 0.8657 0.5847 0.103 Uiso 1 1 calc R . .
H7C H 0.0977 0.9947 0.5414 0.103 Uiso 1 1 calc R . .
C8 C 0.1111(2) 1.15205(18) 0.84284(15) 0.0635(6) Uani 1 1 d . . .
H8A H 0.1377 1.1673 0.7815 0.076 Uiso 1 1 calc R . .
H8B H 0.1632 1.1831 0.8920 0.076 Uiso 1 1 calc R . .
C9 C 0.0782(2) 1.0526(2) 1.19516(13) 0.0569(5) Uani 1 1 d . . .
C10 C 0.02136(19) 0.97396(16) 1.11929(12) 0.0475(4) Uani 1 1 d . . .
H10 H -0.0802 0.9691 1.1260 0.057 Uiso 1 1 calc R . .
C11 C 0.0807(2) 0.84703(16) 1.11505(13) 0.0542(5) Uani 1 1 d . . .
H11A H 0.0710 0.8099 1.1760 0.065 Uiso 1 1 calc R . .
H11B H 0.1795 0.8516 1.1009 0.065 Uiso 1 1 calc R . .
C12 C 0.0094(2) 0.76747(16) 1.04210(12) 0.0563(5) Uani 1 1 d . . .
H12A H 0.0604 0.6926 1.0379 0.068 Uiso 1 1 calc R . .
H12B H -0.0838 0.7488 1.0640 0.068 Uiso 1 1 calc R . .
C13 C -0.0017(2) 0.82058(14) 0.94512(13) 0.0466(4) Uani 1 1 d . . .
C14 C -0.11139(18) 0.91786(15) 0.93395(12) 0.0448(4) Uani 1 1 d . . .
H14 H -0.1874 0.9018 0.9780 0.054 Uiso 1 1 calc R . .
C15 C -0.1742(2) 0.93252(18) 0.83547(13) 0.0525(5) Uani 1 1 d . . .
H15A H -0.1666 0.8579 0.8010 0.063 Uiso 1 1 calc R . .
H15B H -0.2719 0.9541 0.8398 0.063 Uiso 1 1 calc R . .
C16 C 0.0804(2) 0.78494(17) 0.87706(14) 0.0585(5) Uani 1 1 d . . .
H16A H 0.1470 0.7260 0.8880 0.070 Uiso 1 1 calc R . .
H16B H 0.0719 0.8187 0.8179 0.070 Uiso 1 1 calc R . .
C17 C 0.1052(3) 1.0263(3) 1.28357(15) 0.0803(7) Uani 1 1 d . . .
H17A H 0.1399 1.0851 1.3234 0.096 Uiso 1 1 calc R . .
H17B H 0.0895 0.9491 1.3058 0.096 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 C1 1.194(2) . ?
O2 C1 1.334(2) . ?
O2 C2 1.457(2) . ?
O3 C6 1.355(2) . ?
O3 C5 1.465(2) . ?
O4 C6 1.205(3) . ?
C1 C7 1.489(3) . ?
C2 C3 1.508(3) . ?
C2 C15 1.531(3) . ?
C2 H2 0.9800 . ?
C3 C8 1.319(3) . ?
C3 C4 1.510(2) . ?
C4 C5 1.509(2) . ?
C4 C14 1.560(2) . ?
C4 H4 0.9800 . ?
C5 C10 1.536(2) . ?
C5 H5 0.9800 . ?
C6 C9 1.468(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9300 . ?
C8 H8B 0.9300 . ?
C9 C17 1.325(3) . ?
C9 C10 1.498(3) . ?
C10 C11 1.527(2) . ?
C10 H10 0.9800 . ?
C11 C12 1.532(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.514(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C16 1.315(3) . ?
C13 C14 1.519(3) . ?
C14 C15 1.542(2) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9300 . ?
C16 H16B 0.9300 . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9300 . ?

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
C1 O2 C2 116.75(14) . . ?
C6 O3 C5 110.50(16) . . ?
O1 C1 O2 123.79(18) . . ?
O1 C1 C7 124.88(18) . . ?
O2 C1 C7 111.32(17) . . ?
O2 C2 C3 107.35(15) . . ?
O2 C2 C15 113.84(15) . . ?
C3 C2 C15 105.45(14) . . ?
O2 C2 H2 110.0 . . ?
C3 C2 H2 110.0 . . ?
C15 C2 H2 110.0 . . ?
C8 C3 C2 124.54(17) . . ?
C8 C3 C4 126.93(18) . . ?
C2 C3 C4 108.38(15) . . ?
C5 C4 C3 115.13(15) . . ?
C5 C4 C14 113.28(14) . . ?
C3 C4 C14 103.20(13) . . ?
C5 C4 H4 108.3 . . ?
C3 C4 H4 108.3 . . ?
C14 C4 H4 108.3 . . ?
O3 C5 C4 109.61(14) . . ?
O3 C5 C10 105.81(14) . . ?
C4 C5 C10 116.53(15) . . ?
O3 C5 H5 108.2 . . ?
C4 C5 H5 108.2 . . ?
C10 C5 H5 108.2 . . ?
O4 C6 O3 120.8(2) . . ?
O4 C6 C9 129.9(2) . . ?
O3 C6 C9 109.33(18) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 120.0 . . ?
C3 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C17 C9 C6 122.4(2) . . ?
C17 C9 C10 129.4(2) . . ?
C6 C9 C10 108.22(16) . . ?
C9 C10 C11 115.81(16) . . ?
C9 C10 C5 102.06(15) . . ?
C11 C10 C5 112.13(15) . . ?
C9 C10 H10 108.8 . . ?
C11 C10 H10 108.8 . . ?
C5 C10 H10 108.8 . . ?
C10 C11 C12 113.43(15) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 115.51(15) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C16 C13 C12 121.31(18) . . ?
C16 C13 C14 123.54(17) . . ?
C12 C13 C14 115.13(16) . . ?
C13 C14 C15 116.24(15) . . ?
C13 C14 C4 112.25(14) . . ?
C15 C14 C4 102.55(14) . . ?
C13 C14 H14 108.5 . . ?
C15 C14 H14 108.5 . . ?
C4 C14 H14 108.5 . . ?
C2 C15 C14 107.45(15) . . ?
C2 C15 H15A 110.2 . . ?
C14 C15 H15A 110.2 . . ?
C2 C15 H15B 110.2 . . ?
C14 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
C13 C16 H16A 120.0 . . ?
C13 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C9 C17 H17A 120.0 . . ?
C9 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.45
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.095
_refine_diff_density_rms         0.033
