# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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data_No2
_database_code_depnum_ccdc_archive 'CCDC 1851023'
_audit_update_record             
;
2018-06-22 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(E)-3-(1-hydroxyethylidene)-6-methyl-3,5,6,7-tetrahydrobenzofuran-2,4-dione
_chemical_name_common            ?
_chemical_melting_point          357
_chemical_formula_moiety         'C11 H12 O4'
_chemical_formula_sum            'C11 H12 O4'
_chemical_formula_weight         208.21

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   18.4754(11)
_cell_length_b                   10.1860(6)
_cell_length_c                   10.7954(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.8576(18)
_cell_angle_gamma                90
_cell_volume                     2012.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9086
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      25.78

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7068
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54311
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         26.080
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3988
_reflns_number_gt                2431
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+1.9550P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3988
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1616
_refine_ls_wR_factor_gt          0.1372
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.27512(10) 0.45773(18) 0.49764(17) 0.0405(5) Uani 1 1 d . . . . .
C1 C 0.31867(16) 0.5243(3) 0.5971(3) 0.0392(7) Uani 1 1 d . . . . .
C2 C 0.27359(14) 0.6268(3) 0.6390(2) 0.0337(6) Uani 1 1 d . . . . .
C3 C 0.20383(14) 0.6168(2) 0.5587(2) 0.0311(6) Uani 1 1 d . . . . .
C4 C 0.13770(15) 0.6927(3) 0.5492(3) 0.0383(7) Uani 1 1 d . . . . .
C5 C 0.08009(16) 0.6604(3) 0.4413(3) 0.0455(7) Uani 1 1 d . . . . .
H5A H 0.0891 0.7128 0.3689 0.055 Uiso 1 1 calc R U . . .
H5B H 0.0324 0.6863 0.4632 0.055 Uiso 1 1 calc R U . . .
C6 C 0.07672(16) 0.5162(3) 0.4038(3) 0.0442(7) Uani 1 1 d . . . . .
H6 H 0.0622 0.4654 0.4746 0.053 Uiso 1 1 calc R U . . .
C7 C 0.15156(15) 0.4676(3) 0.3812(3) 0.0393(7) Uani 1 1 d . . . . .
H7A H 0.1520 0.3714 0.3808 0.047 Uiso 1 1 calc R U . . .
H7B H 0.1618 0.4982 0.2992 0.047 Uiso 1 1 calc R U . . .
C8 C 0.20851(15) 0.5164(3) 0.4793(2) 0.0337(6) Uani 1 1 d . . . . .
O2 O 0.38034(12) 0.4880(2) 0.6272(2) 0.0551(6) Uani 1 1 d . . . . .
C9 C 0.29590(16) 0.7107(3) 0.7343(3) 0.0408(7) Uani 1 1 d . . . . .
O3 O 0.25300(12) 0.8053(2) 0.7672(2) 0.0548(6) Uani 1 1 d . . . . .
H3 H 0.2129 0.8023 0.7219 0.082 Uiso 1 1 calc R U . . .
C10 C 0.36876(18) 0.7088(3) 0.8117(3) 0.0549(9) Uani 1 1 d . . . . .
H10A H 0.3989 0.7780 0.7842 0.082 Uiso 1 1 calc R U . . .
H10B H 0.3919 0.6245 0.8027 0.082 Uiso 1 1 calc R U . . .
H10C H 0.3631 0.7227 0.8987 0.082 Uiso 1 1 calc R U . . .
O4 O 0.12916(12) 0.7828(2) 0.6234(2) 0.0533(6) Uani 1 1 d . . . . .
C11 C 0.01967(19) 0.4928(4) 0.2914(3) 0.0635(10) Uani 1 1 d . . . . .
H11A H -0.0277 0.5217 0.3101 0.095 Uiso 1 1 calc R U . . .
H11B H 0.0176 0.3999 0.2715 0.095 Uiso 1 1 calc R U . . .
H11C H 0.0325 0.5417 0.2204 0.095 Uiso 1 1 calc R U . . .
O5 O 0.23331(11) 0.30243(19) 0.74280(18) 0.0454(5) Uani 1 1 d . . . . .
C12 C 0.18704(18) 0.2372(3) 0.6435(3) 0.0456(8) Uani 1 1 d . . . . .
C13 C 0.23066(15) 0.1307(3) 0.6003(2) 0.0359(7) Uani 1 1 d . . . . .
C14 C 0.30071(14) 0.1386(3) 0.6798(2) 0.0333(6) Uani 1 1 d . . . . .
C15 C 0.36496(16) 0.0588(3) 0.6871(3) 0.0409(7) Uani 1 1 d . . . . .
C16 C 0.42457(17) 0.0881(3) 0.7930(3) 0.0539(8) Uani 1 1 d . . . . .
H16A H 0.4715 0.0620 0.7678 0.065 Uiso 1 1 calc R U . . .
H16B H 0.4167 0.0338 0.8650 0.065 Uiso 1 1 calc R U . . .
C17 C 0.42974(17) 0.2302(3) 0.8340(3) 0.0544(9) Uani 1 1 d . . . . .
H17 H 0.4455 0.2817 0.7646 0.065 Uiso 1 1 calc R U . . .
C18 C 0.35667(16) 0.2836(3) 0.8578(3) 0.0430(7) Uani 1 1 d . . . . .
H18A H 0.3460 0.2532 0.9396 0.052 Uiso 1 1 calc R U . . .
H18B H 0.3584 0.3797 0.8593 0.052 Uiso 1 1 calc R U . . .
C19 C 0.29842(15) 0.2396(3) 0.7596(3) 0.0369(7) Uani 1 1 d . . . . .
O6 O 0.12652(12) 0.2759(2) 0.6157(2) 0.0599(6) Uani 1 1 d . . . . .
C20 C 0.20500(17) 0.0460(3) 0.5086(3) 0.0465(8) Uani 1 1 d . . . . .
O7 O 0.24575(13) -0.0523(2) 0.4743(2) 0.0586(6) Uani 1 1 d . . . . .
H7 H 0.2863 -0.0515 0.5182 0.088 Uiso 1 1 calc R U . . .
C21 C 0.13016(18) 0.0495(4) 0.4368(3) 0.0618(10) Uani 1 1 d . . . . .
H21A H 0.1330 0.0340 0.3490 0.093 Uiso 1 1 calc R U . . .
H21B H 0.1084 0.1349 0.4468 0.093 Uiso 1 1 calc R U . . .
H21C H 0.1003 -0.0180 0.4680 0.093 Uiso 1 1 calc R U . . .
O8 O 0.37056(12) -0.0332(2) 0.6134(2) 0.0549(6) Uani 1 1 d . . . . .
C22 C 0.48785(19) 0.2473(4) 0.9473(3) 0.0690(11) Uani 1 1 d . . . . .
H22A H 0.4742 0.1973 1.0170 0.104 Uiso 1 1 calc R U . . .
H22B H 0.4919 0.3395 0.9698 0.104 Uiso 1 1 calc R U . . .
H22C H 0.5345 0.2160 0.9273 0.104 Uiso 1 1 calc R U . . .


_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 C8 1.358(3) . ?
O1 C1 1.422(3) . ?
C1 O2 1.200(3) . ?
C1 C2 1.447(4) . ?
C2 C9 1.358(4) . ?
C2 C3 1.455(4) . ?
C3 C8 1.345(4) . ?
C3 C4 1.438(4) . ?
C4 O4 1.242(3) 1 ?
C4 O4 1.242(3) . ?
C4 C5 1.503(4) . ?
C5 C6 1.522(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C11 1.514(4) . ?
C6 C7 1.520(4) . ?
C6 H6 0.9900 . ?
C7 C8 1.473(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C9 O3 1.327(3) . ?
C9 C10 1.484(4) . ?
O3 H3 0.8300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
O4 O4 0.000(5) 1 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
O5 C19 1.353(3) . ?
O5 C12 1.439(4) . ?
C12 O6 1.185(4) . ?
C12 C13 1.466(4) . ?
C13 C20 1.350(4) . ?
C13 C14 1.454(4) . ?
C14 C19 1.346(4) . ?
C14 C15 1.432(4) . ?
C15 O8 1.243(3) 1 ?
C15 O8 1.243(3) . ?
C15 C16 1.505(4) . ?
C16 C17 1.513(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.510(4) . ?
C17 C22 1.523(4) . ?
C17 H17 0.9900 . ?
C18 C19 1.473(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C20 O7 1.335(4) . ?
C20 C21 1.490(4) . ?
O7 H7 0.8300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
O8 O8 0.000(6) 1 ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?

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
C8 O1 C1 108.0(2) . . ?
O2 C1 O1 118.5(3) . . ?
O2 C1 C2 134.7(3) . . ?
O1 C1 C2 106.9(2) . . ?
C9 C2 C1 124.3(3) . . ?
C9 C2 C3 130.4(3) . . ?
C1 C2 C3 105.3(2) . . ?
C8 C3 C4 119.5(3) . . ?
C8 C3 C2 107.7(2) . . ?
C4 C3 C2 132.8(2) . . ?
O4 C4 C3 122.2(3) 1 . ?
O4 C4 C3 122.2(3) . . ?
O4 C4 C5 121.5(3) 1 . ?
O4 C4 C5 121.5(3) . . ?
C3 C4 C5 116.2(2) . . ?
C4 C5 C6 114.6(2) . . ?
C4 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C11 C6 C7 111.6(3) . . ?
C11 C6 C5 111.3(3) . . ?
C7 C6 C5 110.6(2) . . ?
C11 C6 H6 107.7 . . ?
C7 C6 H6 107.7 . . ?
C5 C6 H6 107.7 . . ?
C8 C7 C6 110.5(2) . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C3 C8 O1 112.2(2) . . ?
C3 C8 C7 127.8(3) . . ?
O1 C8 C7 120.0(2) . . ?
O3 C9 C2 122.0(3) . . ?
O3 C9 C10 112.8(3) . . ?
C2 C9 C10 125.2(3) . . ?
C9 O3 H3 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C19 O5 C12 108.0(2) . . ?
O6 C12 O5 118.6(3) . . ?
O6 C12 C13 134.9(3) . . ?
O5 C12 C13 106.4(2) . . ?
C20 C13 C14 131.6(3) . . ?
C20 C13 C12 123.6(3) . . ?
C14 C13 C12 104.8(2) . . ?
C19 C14 C15 119.8(3) . . ?
C19 C14 C13 108.5(2) . . ?
C15 C14 C13 131.7(3) . . ?
O8 C15 C14 122.3(3) 1 . ?
O8 C15 C14 122.3(3) . . ?
O8 C15 C16 121.3(3) 1 . ?
O8 C15 C16 121.3(3) . . ?
C14 C15 C16 116.4(3) . . ?
C15 C16 C17 115.0(3) . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 111.8(3) . . ?
C18 C17 C22 111.7(3) . . ?
C16 C17 C22 110.7(3) . . ?
C18 C17 H17 107.4 . . ?
C16 C17 H17 107.4 . . ?
C22 C17 H17 107.4 . . ?
C19 C18 C17 110.5(2) . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C14 C19 O5 112.4(3) . . ?
C14 C19 C18 127.5(3) . . ?
O5 C19 C18 120.1(3) . . ?
O7 C20 C13 121.9(3) . . ?
O7 C20 C21 113.1(3) . . ?
C13 C20 C21 125.0(3) . . ?
C20 O7 H7 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C8 O1 C1 O2 -179.2(2) . . . . ?
C8 O1 C1 C2 0.6(3) . . . . ?
O2 C1 C2 C9 -1.1(5) . . . . ?
O1 C1 C2 C9 179.1(2) . . . . ?
O2 C1 C2 C3 179.0(3) . . . . ?
O1 C1 C2 C3 -0.8(3) . . . . ?
C9 C2 C3 C8 -179.2(3) . . . . ?
C1 C2 C3 C8 0.7(3) . . . . ?
C9 C2 C3 C4 2.9(5) . . . . ?
C1 C2 C3 C4 -177.2(3) . . . . ?
C8 C3 C4 O4 176.8(3) . . . 1 ?
C2 C3 C4 O4 -5.5(5) . . . 1 ?
C8 C3 C4 O4 176.8(3) . . . . ?
C2 C3 C4 O4 -5.5(5) . . . . ?
C8 C3 C4 C5 -5.3(4) . . . . ?
C2 C3 C4 C5 172.4(3) . . . . ?
O4 C4 C5 C6 -148.7(3) 1 . . . ?
O4 C4 C5 C6 -148.7(3) . . . . ?
C3 C4 C5 C6 33.4(4) . . . . ?
C4 C5 C6 C11 -177.6(3) . . . . ?
C4 C5 C6 C7 -52.9(3) . . . . ?
C11 C6 C7 C8 167.8(3) . . . . ?
C5 C6 C7 C8 43.2(3) . . . . ?
C4 C3 C8 O1 177.9(2) . . . . ?
C2 C3 C8 O1 -0.4(3) . . . . ?
C4 C3 C8 C7 -2.3(4) . . . . ?
C2 C3 C8 C7 179.5(3) . . . . ?
C1 O1 C8 C3 -0.2(3) . . . . ?
C1 O1 C8 C7 180.0(2) . . . . ?
C6 C7 C8 C3 -17.9(4) . . . . ?
C6 C7 C8 O1 161.9(2) . . . . ?
C1 C2 C9 O3 178.3(3) . . . . ?
C3 C2 C9 O3 -1.9(5) . . . . ?
C1 C2 C9 C10 -1.4(4) . . . . ?
C3 C2 C9 C10 178.5(3) . . . . ?
C3 C4 O4 O4 0.0(6) . . . 1 ?
C5 C4 O4 O4 0.0(5) . . . 1 ?
C19 O5 C12 O6 178.5(3) . . . . ?
C19 O5 C12 C13 -1.0(3) . . . . ?
O6 C12 C13 C20 -0.6(5) . . . . ?
O5 C12 C13 C20 178.9(2) . . . . ?
O6 C12 C13 C14 -178.5(3) . . . . ?
O5 C12 C13 C14 1.0(3) . . . . ?
C20 C13 C14 C19 -178.3(3) . . . . ?
C12 C13 C14 C19 -0.6(3) . . . . ?
C20 C13 C14 C15 -0.5(5) . . . . ?
C12 C13 C14 C15 177.2(3) . . . . ?
C19 C14 C15 O8 -178.0(3) . . . 1 ?
C13 C14 C15 O8 4.4(5) . . . 1 ?
C19 C14 C15 O8 -178.0(3) . . . . ?
C13 C14 C15 O8 4.4(5) . . . . ?
C19 C14 C15 C16 4.8(4) . . . . ?
C13 C14 C15 C16 -172.8(3) . . . . ?
O8 C15 C16 C17 151.7(3) 1 . . . ?
O8 C15 C16 C17 151.7(3) . . . . ?
C14 C15 C16 C17 -31.0(4) . . . . ?
C15 C16 C17 C18 50.6(4) . . . . ?
C15 C16 C17 C22 175.9(3) . . . . ?
C16 C17 C18 C19 -42.4(4) . . . . ?
C22 C17 C18 C19 -167.1(3) . . . . ?
C15 C14 C19 O5 -178.2(2) . . . . ?
C13 C14 C19 O5 -0.1(3) . . . . ?
C15 C14 C19 C18 1.3(4) . . . . ?
C13 C14 C19 C18 179.3(3) . . . . ?
C12 O5 C19 C14 0.7(3) . . . . ?
C12 O5 C19 C18 -178.8(2) . . . . ?
C17 C18 C19 C14 18.5(4) . . . . ?
C17 C18 C19 O5 -162.1(2) . . . . ?
C14 C13 C20 O7 -0.6(5) . . . . ?
C12 C13 C20 O7 -178.0(3) . . . . ?
C14 C13 C20 C21 178.6(3) . . . . ?
C12 C13 C20 C21 1.2(4) . . . . ?
C14 C15 O8 O8 0.0(2) . . . 1 ?
C16 C15 O8 O8 0.0(3) . . . 1 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O8 0.83 1.75 2.581(3) 174.4 1
O3 H3 O4 0.83 1.76 2.593(3) 175.5 1

_refine_diff_density_max         0.458
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/ethyl acetate'
