# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1017041'
_audit_update_record             
;
2014-07-30 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 O6'
_chemical_formula_sum            'C23 H22 O6'
_chemical_formula_weight         394.41

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'
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           triclinic
_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                   8.8905(5)
_cell_length_b                   11.0671(5)
_cell_length_c                   11.5086(6)
_cell_angle_alpha                89.950(2)
_cell_angle_beta                 75.602(2)
_cell_angle_gamma                72.860(2)
_cell_volume                     1044.87(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      2.4825
_cell_measurement_theta_max      27.640

_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    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   Multi-scan
_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  'Bruker Apex-II CCD diffractometer'
_diffrn_measurement_method       'Thin slice φ & ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17821
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.75
_reflns_number_total             4874
_reflns_number_gt                4118
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0779P)²+0.2304P] 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         4874
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1491
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.35462(11) 0.42522(8) 0.24099(10) 0.0529(3) Uani 1 1 d . . .
O2 O 0.37432(16) 0.69035(13) 0.10354(11) 0.0734(4) Uani 1 1 d . . .
O3 O 0.90272(12) 0.33307(11) 0.11740(12) 0.0640(3) Uani 1 1 d . . .
O4 O 0.83765(15) 0.15460(11) 0.15022(14) 0.0775(4) Uani 1 1 d . . .
O5 O 0.38204(14) 0.69417(9) 0.39195(9) 0.0554(3) Uani 1 1 d . . .
O6 O 0.33179(16) 0.51674(12) 0.46232(11) 0.0686(3) Uani 1 1 d . . .
C1 C 0.49250(16) 0.32198(12) 0.21252(12) 0.0419(3) Uani 1 1 d . . .
C2 C 0.63001(16) 0.35394(12) 0.18235(12) 0.0445(3) Uani 1 1 d . . .
C3 C 0.58843(18) 0.49613(14) 0.18715(16) 0.0570(4) Uani 1 1 d . . .
H3A H 0.6108 0.5257 0.1072 0.068 Uiso 1 1 calc R . .
H3B H 0.6477 0.5267 0.2347 0.068 Uiso 1 1 calc R . .
C4 C 0.40464(16) 0.53711(12) 0.24815(13) 0.0462(3) Uani 1 1 d . . .
C5 C 0.45410(16) 0.20151(12) 0.22585(12) 0.0433(3) Uani 1 1 d . . .
C6 C 0.3357(2) 0.19167(15) 0.32673(16) 0.0608(4) Uani 1 1 d . . .
H6 H 0.2826 0.2606 0.3834 0.073 Uiso 1 1 calc R . .
C7 C 0.2965(3) 0.08021(18) 0.3433(2) 0.0768(5) Uani 1 1 d . . .
H7 H 0.2189 0.0734 0.4119 0.092 Uiso 1 1 calc R . .
C8 C 0.3721(3) -0.02088(16) 0.2585(2) 0.0753(5) Uani 1 1 d . . .
H8 H 0.3448 -0.0958 0.2693 0.090 Uiso 1 1 calc R . .
C9 C 0.4870(3) -0.01135(15) 0.15840(18) 0.0701(5) Uani 1 1 d . . .
H9 H 0.5371 -0.0799 0.1010 0.084 Uiso 1 1 calc R . .
C10 C 0.5302(2) 0.09928(14) 0.14113(15) 0.0560(4) Uani 1 1 d . . .
H10 H 0.6097 0.1046 0.0731 0.067 Uiso 1 1 calc R . .
C11 C 0.79712(17) 0.26775(14) 0.14918(13) 0.0499(3) Uani 1 1 d . . .
C12 C 1.07456(19) 0.25970(19) 0.0837(2) 0.0730(5) Uani 1 1 d . . .
H12A H 1.0924 0.1862 0.0302 0.088 Uiso 1 1 calc R . .
H12B H 1.1104 0.2307 0.1547 0.088 Uiso 1 1 calc R . .
C13 C 1.1656(2) 0.34348(19) 0.0226(2) 0.0744(5) Uani 1 1 d . . .
H13A H 1.1322 0.3688 -0.0491 0.112 Uiso 1 1 calc R . .
H13B H 1.2802 0.2990 0.0019 0.112 Uiso 1 1 calc R . .
H13C H 1.1437 0.4173 0.0754 0.112 Uiso 1 1 calc R . .
C14 C 0.30389(18) 0.64317(13) 0.18549(12) 0.0469(3) Uani 1 1 d . . .
C15 C 0.12348(17) 0.69004(12) 0.23268(12) 0.0451(3) Uani 1 1 d . . .
C16 C 0.03316(18) 0.62257(14) 0.30663(14) 0.0511(3) Uani 1 1 d . . .
H16 H 0.0858 0.5438 0.3291 0.061 Uiso 1 1 calc R . .
C17 C -0.1342(2) 0.67205(17) 0.34672(16) 0.0627(4) Uani 1 1 d . . .
H17 H -0.1944 0.6258 0.3944 0.075 Uiso 1 1 calc R . .
C18 C -0.2116(2) 0.78988(19) 0.31608(19) 0.0736(5) Uani 1 1 d . . .
H18 H -0.3243 0.8234 0.3438 0.088 Uiso 1 1 calc R . .
C19 C -0.1241(2) 0.85845(18) 0.2448(2) 0.0732(5) Uani 1 1 d . . .
H19 H -0.1774 0.9385 0.2254 0.088 Uiso 1 1 calc R . .
C20 C 0.0424(2) 0.80882(15) 0.20207(16) 0.0591(4) Uani 1 1 d . . .
H20 H 0.1011 0.8548 0.1525 0.071 Uiso 1 1 calc R . .
C21 C 0.36736(16) 0.57881(12) 0.38137(13) 0.0466(3) Uani 1 1 d . . .
C22 C 0.3347(3) 0.75652(19) 0.51233(17) 0.0748(5) Uani 1 1 d . . .
H22A H 0.3905 0.8196 0.5134 0.090 Uiso 1 1 calc R . .
H22B H 0.3661 0.6946 0.5685 0.090 Uiso 1 1 calc R . .
C23 C 0.1555(3) 0.8185(3) 0.5495(2) 0.0998(8) Uani 1 1 d . . .
H23A H 0.1227 0.8701 0.4877 0.150 Uiso 1 1 calc R . .
H23B H 0.1272 0.8706 0.6230 0.150 Uiso 1 1 calc R . .
H23C H 0.1009 0.7547 0.5618 0.150 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 1.3750(16) . ?
O1 C4 1.4426(15) . ?
O2 C14 1.2052(17) . ?
O3 C11 1.3291(18) . ?
O3 C12 1.4555(19) . ?
O4 C11 1.1976(19) . ?
O5 C21 1.3297(16) . ?
O5 C22 1.454(2) . ?
O6 C21 1.1917(17) . ?
C1 C2 1.3356(18) . ?
C1 C5 1.4696(17) . ?
C2 C11 1.4650(19) . ?
C2 C3 1.5043(19) . ?
C3 C4 1.5368(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C21 1.527(2) . ?
C4 C14 1.549(2) . ?
C5 C10 1.382(2) . ?
C5 C6 1.388(2) . ?
C6 C7 1.378(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.364(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C12 C13 1.472(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.488(2) . ?
C15 C20 1.392(2) . ?
C15 C16 1.3926(19) . ?
C16 C17 1.380(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C22 C23 1.486(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C1 O1 C4 107.93(10) . . ?
C11 O3 C12 116.41(13) . . ?
C21 O5 C22 117.64(13) . . ?
C2 C1 O1 113.06(11) . . ?
C2 C1 C5 134.74(12) . . ?
O1 C1 C5 112.17(11) . . ?
C1 C2 C11 127.04(13) . . ?
C1 C2 C3 109.24(12) . . ?
C11 C2 C3 123.72(12) . . ?
C2 C3 C4 101.56(10) . . ?
C2 C3 H3A 111.5 . . ?
C4 C3 H3A 111.5 . . ?
C2 C3 H3B 111.5 . . ?
C4 C3 H3B 111.5 . . ?
H3A C3 H3B 109.3 . . ?
O1 C4 C21 107.29(11) . . ?
O1 C4 C3 105.67(10) . . ?
C21 C4 C3 112.04(12) . . ?
O1 C4 C14 108.90(11) . . ?
C21 C4 C14 109.36(10) . . ?
C3 C4 C14 113.30(12) . . ?
C10 C5 C6 119.42(13) . . ?
C10 C5 C1 122.28(13) . . ?
C6 C5 C1 118.30(12) . . ?
C7 C6 C5 120.26(16) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C6 120.04(19) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 120.00(15) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.82(16) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C9 119.44(16) . . ?
C5 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
O4 C11 O3 123.16(14) . . ?
O4 C11 C2 126.61(14) . . ?
O3 C11 C2 110.23(12) . . ?
O3 C12 C13 107.24(14) . . ?
O3 C12 H12A 110.3 . . ?
C13 C12 H12A 110.3 . . ?
O3 C12 H12B 110.3 . . ?
C13 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C15 121.48(14) . . ?
O2 C14 C4 119.07(13) . . ?
C15 C14 C4 119.33(11) . . ?
C20 C15 C16 118.87(14) . . ?
C20 C15 C14 117.56(13) . . ?
C16 C15 C14 123.56(12) . . ?
C17 C16 C15 120.29(14) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.88(16) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.54(17) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 120.09(16) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 120.31(16) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
O6 C21 O5 125.88(15) . . ?
O6 C21 C4 124.93(13) . . ?
O5 C21 C4 109.18(11) . . ?
O5 C22 C23 109.89(16) . . ?
O5 C22 H22A 109.7 . . ?
C23 C22 H22A 109.7 . . ?
O5 C22 H22B 109.7 . . ?
C23 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.75
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.053
