# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_dm14281
_database_code_depnum_ccdc_archive 'CCDC 1422696'
_audit_update_record             
;
2015-09-06 deposited with the CCDC.
2016-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'(4S,5S,9S,10R)-13,14-seco-13-oxo-18-hydroxy-ent-abieta-7-en-14- oic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H32 O4'
_chemical_formula_weight         336.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   11.8465(5)
_cell_length_b                   23.7593(10)
_cell_length_c                   6.5189(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1834.84(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    2516
_cell_measurement_theta_min      4.17
_cell_measurement_theta_max      67.49

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.662
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4908
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9366
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.170
_diffrn_reflns_theta_max         69.456
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3332
_reflns_number_gt                3001
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_fraction_full    0.970

_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 (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)+(0.1061P)²+0.3638P] 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_abs_structure_details 
; 
 Flack x determined using 1131 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.10(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3332
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1632
_refine_ls_wR_factor_gt          0.1580
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.4699(2) 1.00808(11) 0.1799(5) 0.0441(7) Uani 1 1 d . . . . .
O2 O 0.4332(3) 1.00763(14) 0.5115(5) 0.0588(9) Uani 1 1 d . . . . .
H2 H 0.4897 1.0290 0.5144 0.088 Uiso 1 1 calc R U . . .
O3 O 0.7108(2) 0.89635(13) -0.0519(4) 0.0448(7) Uani 1 1 d . . . . .
O4 O -0.0561(2) 0.89842(12) 0.0305(5) 0.0498(8) Uani 1 1 d . . . . .
H3 H -0.1232 0.9028 -0.0080 0.075 Uiso 1 1 calc R U . . .
C1 C 0.2832(3) 0.81559(15) -0.0628(6) 0.0321(8) Uani 1 1 d . . . . .
H1C H 0.2709 0.8437 -0.1727 0.038 Uiso 1 1 calc R U . . .
H1D H 0.3584 0.7985 -0.0852 0.038 Uiso 1 1 calc R U . . .
C2 C 0.1937(3) 0.76985(16) -0.0812(7) 0.0401(9) Uani 1 1 d . . . . .
H2A H 0.2086 0.7399 0.0209 0.048 Uiso 1 1 calc R U . . .
H2B H 0.1971 0.7528 -0.2196 0.048 Uiso 1 1 calc R U . . .
C3 C 0.0766(3) 0.79462(15) -0.0451(6) 0.0349(8) Uani 1 1 d . . . . .
H3A H 0.0198 0.7642 -0.0572 0.042 Uiso 1 1 calc R U . . .
H3B H 0.0606 0.8227 -0.1533 0.042 Uiso 1 1 calc R U . . .
C4 C 0.0641(3) 0.82290(14) 0.1661(6) 0.0289(7) Uani 1 1 d . . . . .
C5 C 0.1613(3) 0.86641(13) 0.1934(5) 0.0254(7) Uani 1 1 d . . . . .
H5 H 0.1455 0.8967 0.0909 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1576(3) 0.89593(15) 0.4041(6) 0.0322(8) Uani 1 1 d . . . . .
H6A H 0.0856 0.9168 0.4172 0.039 Uiso 1 1 calc R U . . .
H6B H 0.1599 0.8672 0.5139 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2536(3) 0.93574(14) 0.4317(6) 0.0304(8) Uani 1 1 d . . . . .
H7 H 0.2527 0.9600 0.5476 0.036 Uiso 1 1 calc R U . . .
C8 C 0.3415(3) 0.93926(13) 0.3020(6) 0.0283(7) Uani 1 1 d . . . . .
C9 C 0.3562(2) 0.90058(13) 0.1195(5) 0.0261(7) Uani 1 1 d . . . . .
H9 H 0.3247 0.9211 -0.0016 0.031 Uiso 1 1 calc R U . . .
C10 C 0.2835(3) 0.84603(13) 0.1451(5) 0.0250(7) Uani 1 1 d . . . . .
C11 C 0.4823(3) 0.88834(15) 0.0686(6) 0.0305(8) Uani 1 1 d . . . . .
H11A H 0.5304 0.9048 0.1774 0.037 Uiso 1 1 calc R U . . .
H11B H 0.4946 0.8471 0.0691 0.037 Uiso 1 1 calc R U . . .
C12 C 0.5187(3) 0.91191(17) -0.1378(6) 0.0345(8) Uani 1 1 d . . . . .
H12A H 0.4761 0.8921 -0.2467 0.041 Uiso 1 1 calc R U . . .
H12B H 0.4969 0.9521 -0.1436 0.041 Uiso 1 1 calc R U . . .
C13 C 0.6430(3) 0.90737(15) -0.1855(6) 0.0320(8) Uani 1 1 d . . . . .
C14 C 0.4190(3) 0.98818(14) 0.3228(6) 0.0315(8) Uani 1 1 d . . . . .
C15 C 0.6780(3) 0.91672(15) -0.4058(6) 0.0336(8) Uani 1 1 d . . . . .
H15 H 0.6180 0.9394 -0.4752 0.040 Uiso 1 1 calc R U . . .
C16 C 0.6848(3) 0.85935(17) -0.5111(6) 0.0394(9) Uani 1 1 d . . . . .
H16A H 0.7417 0.8361 -0.4424 0.059 Uiso 1 1 calc R U . . .
H16B H 0.7058 0.8645 -0.6553 0.059 Uiso 1 1 calc R U . . .
H16C H 0.6111 0.8407 -0.5032 0.059 Uiso 1 1 calc R U . . .
C17 C 0.7890(3) 0.94816(18) -0.4237(7) 0.0466(10) Uani 1 1 d . . . . .
H17A H 0.7827 0.9846 -0.3543 0.070 Uiso 1 1 calc R U . . .
H17B H 0.8069 0.9542 -0.5688 0.070 Uiso 1 1 calc R U . . .
H17C H 0.8492 0.9260 -0.3594 0.070 Uiso 1 1 calc R U . . .
C18 C -0.0506(3) 0.85342(15) 0.1726(6) 0.0351(8) Uani 1 1 d . . . . .
H18A H -0.1115 0.8261 0.1418 0.042 Uiso 1 1 calc R U . . .
H18B H -0.0635 0.8682 0.3126 0.042 Uiso 1 1 calc R U . . .
C19 C 0.0565(3) 0.77763(15) 0.3325(7) 0.0401(9) Uani 1 1 d . . . . .
H19A H 0.0568 0.7955 0.4680 0.060 Uiso 1 1 calc R U . . .
H19B H 0.1214 0.7522 0.3212 0.060 Uiso 1 1 calc R U . . .
H19C H -0.0135 0.7562 0.3151 0.060 Uiso 1 1 calc R U . . .
C20 C 0.3334(3) 0.80841(13) 0.3139(6) 0.0301(7) Uani 1 1 d . . . . .
H20A H 0.2885 0.7739 0.3256 0.045 Uiso 1 1 calc R U . . .
H20B H 0.3321 0.8286 0.4450 0.045 Uiso 1 1 calc R U . . .
H20C H 0.4114 0.7987 0.2789 0.045 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 C14 1.207(5) . ?
O2 C14 1.325(5) . ?
O2 H2 0.8400 . ?
O3 C13 1.214(4) . ?
O4 C18 1.416(4) . ?
O4 H3 0.8400 . ?
C1 C2 1.523(5) . ?
C1 C10 1.536(5) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C2 C3 1.525(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.539(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C19 1.531(5) . ?
C4 C18 1.542(4) . ?
C4 C5 1.557(4) . ?
C5 C6 1.543(5) . ?
C5 C10 1.558(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.490(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.343(5) . ?
C7 H7 0.9500 . ?
C8 C14 1.487(4) . ?
C8 C9 1.514(5) . ?
C9 C11 1.557(4) . ?
C9 C10 1.566(4) . ?
C9 H9 1.0000 . ?
C10 C20 1.536(4) . ?
C11 C12 1.520(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.509(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C15 1.511(5) . ?
C15 C17 1.517(5) . ?
C15 C16 1.528(5) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C14 O2 H2 109.5 . . ?
C18 O4 H3 109.5 . . ?
C2 C1 C10 114.0(3) . . ?
C2 C1 H1C 108.8 . . ?
C10 C1 H1C 108.8 . . ?
C2 C1 H1D 108.8 . . ?
C10 C1 H1D 108.8 . . ?
H1C C1 H1D 107.6 . . ?
C1 C2 C3 110.2(3) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C2 C3 C4 113.2(3) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
C19 C4 C3 109.4(3) . . ?
C19 C4 C18 105.0(3) . . ?
C3 C4 C18 108.3(3) . . ?
C19 C4 C5 115.4(3) . . ?
C3 C4 C5 108.8(3) . . ?
C18 C4 C5 109.7(3) . . ?
C6 C5 C4 112.5(3) . . ?
C6 C5 C10 110.4(3) . . ?
C4 C5 C10 117.2(2) . . ?
C6 C5 H5 105.2 . . ?
C4 C5 H5 105.2 . . ?
C10 C5 H5 105.2 . . ?
C7 C6 C5 112.0(3) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 123.7(3) . . ?
C8 C7 H7 118.1 . . ?
C6 C7 H7 118.1 . . ?
C7 C8 C14 118.0(3) . . ?
C7 C8 C9 123.1(3) . . ?
C14 C8 C9 118.3(3) . . ?
C8 C9 C11 113.1(3) . . ?
C8 C9 C10 110.8(3) . . ?
C11 C9 C10 113.3(3) . . ?
C8 C9 H9 106.4 . . ?
C11 C9 H9 106.4 . . ?
C10 C9 H9 106.4 . . ?
C20 C10 C1 111.0(3) . . ?
C20 C10 C5 113.2(3) . . ?
C1 C10 C5 108.8(3) . . ?
C20 C10 C9 110.3(3) . . ?
C1 C10 C9 107.3(3) . . ?
C5 C10 C9 106.0(2) . . ?
C12 C11 C9 113.0(3) . . ?
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 . . ?
C13 C12 C11 115.6(3) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.4 . . ?
O3 C13 C12 121.0(3) . . ?
O3 C13 C15 122.1(3) . . ?
C12 C13 C15 116.9(3) . . ?
O1 C14 O2 121.1(3) . . ?
O1 C14 C8 123.0(3) . . ?
O2 C14 C8 115.8(3) . . ?
C13 C15 C17 112.5(3) . . ?
C13 C15 C16 108.1(3) . . ?
C17 C15 C16 111.0(3) . . ?
C13 C15 H15 108.4 . . ?
C17 C15 H15 108.4 . . ?
C16 C15 H15 108.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 C4 112.2(3) . . ?
O4 C18 H18A 109.2 . . ?
C4 C18 H18A 109.2 . . ?
O4 C18 H18B 109.2 . . ?
C4 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C10 C1 C2 C3 57.8(4) . . . . ?
C1 C2 C3 C4 -58.4(4) . . . . ?
C2 C3 C4 C19 -74.0(4) . . . . ?
C2 C3 C4 C18 172.0(3) . . . . ?
C2 C3 C4 C5 52.9(4) . . . . ?
C19 C4 C5 C6 -55.1(4) . . . . ?
C3 C4 C5 C6 -178.5(3) . . . . ?
C18 C4 C5 C6 63.2(4) . . . . ?
C19 C4 C5 C10 74.4(4) . . . . ?
C3 C4 C5 C10 -49.0(4) . . . . ?
C18 C4 C5 C10 -167.3(3) . . . . ?
C4 C5 C6 C7 177.7(3) . . . . ?
C10 C5 C6 C7 44.7(4) . . . . ?
C5 C6 C7 C8 -9.1(5) . . . . ?
C6 C7 C8 C14 167.7(3) . . . . ?
C6 C7 C8 C9 -3.8(5) . . . . ?
C7 C8 C9 C11 -147.7(3) . . . . ?
C14 C8 C9 C11 40.8(4) . . . . ?
C7 C8 C9 C10 -19.2(4) . . . . ?
C14 C8 C9 C10 169.3(3) . . . . ?
C2 C1 C10 C20 73.9(4) . . . . ?
C2 C1 C10 C5 -51.3(4) . . . . ?
C2 C1 C10 C9 -165.6(3) . . . . ?
C6 C5 C10 C20 54.6(3) . . . . ?
C4 C5 C10 C20 -75.9(4) . . . . ?
C6 C5 C10 C1 178.6(3) . . . . ?
C4 C5 C10 C1 48.1(4) . . . . ?
C6 C5 C10 C9 -66.3(3) . . . . ?
C4 C5 C10 C9 163.2(3) . . . . ?
C8 C9 C10 C20 -70.8(3) . . . . ?
C11 C9 C10 C20 57.5(4) . . . . ?
C8 C9 C10 C1 168.2(3) . . . . ?
C11 C9 C10 C1 -63.5(4) . . . . ?
C8 C9 C10 C5 52.0(3) . . . . ?
C11 C9 C10 C5 -179.6(3) . . . . ?
C8 C9 C11 C12 -114.6(3) . . . . ?
C10 C9 C11 C12 118.3(3) . . . . ?
C9 C11 C12 C13 173.2(3) . . . . ?
C11 C12 C13 O3 -14.3(5) . . . . ?
C11 C12 C13 C15 165.3(3) . . . . ?
C7 C8 C14 O1 -150.1(4) . . . . ?
C9 C8 C14 O1 21.8(5) . . . . ?
C7 C8 C14 O2 32.7(5) . . . . ?
C9 C8 C14 O2 -155.4(3) . . . . ?
O3 C13 C15 C17 -38.0(5) . . . . ?
C12 C13 C15 C17 142.5(3) . . . . ?
O3 C13 C15 C16 85.0(4) . . . . ?
C12 C13 C15 C16 -94.5(4) . . . . ?
C19 C4 C18 O4 178.0(3) . . . . ?
C3 C4 C18 O4 -65.1(4) . . . . ?
C5 C4 C18 O4 53.5(4) . . . . ?

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
O2 H2 O4 0.84 1.90 2.668(4) 151.7 4_575
O4 H3 O3 0.84 1.99 2.812(3) 165.2 1_455
C12 H12B O1 0.99 2.51 3.138(5) 120.8 .

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.057

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_chemical_compound_source        plant
