# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mo_tok_dina_csv5_mo2_0ma_a_pl
_database_code_depnum_ccdc_archive 'CCDC 1994762'
loop_
_audit_author_name
_audit_author_address
'Christoph Janiak'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2020-04-03 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            chrysosplentin
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 O8'
_chemical_formula_sum            'C19 H18 O8'
_chemical_formula_weight         374.33

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.2577(3)
_cell_length_b                   17.3639(8)
_cell_length_c                   13.3620(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.789(2)
_cell_angle_gamma                90
_cell_volume                     1675.32(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    136(2)
_cell_measurement_reflns_used    4452
_cell_measurement_theta_min      2.802
_cell_measurement_theta_max      22.863

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5541
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      136(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans, φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29961
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.532
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6958
_reflns_number_gt                5346
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4.5.3 (Crystal Impact, 2018)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'

_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     
'w=1/[σ²(Fo²)+(0.0438P)²+0.1359P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6958
_refine_ls_number_parameters     512
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0987
_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 -0.0482(3) 0.54749(14) 0.05069(17) 0.0238(6) Uani 1 1 d . . . . .
C1' C -0.1219(5) 0.4891(2) -0.1053(3) 0.0241(8) Uani 1 1 d . . . . .
O2 O -0.1822(4) 0.34798(16) 0.0113(2) 0.0324(6) Uani 1 1 d . . . . .
C2 C -0.0993(5) 0.4791(2) 0.0046(3) 0.0228(8) Uani 1 1 d . . . . .
C2' C 0.0074(5) 0.5360(2) -0.1479(3) 0.0240(8) Uani 1 1 d . . . . .
H2' H 0.102398 0.560930 -0.105717 0.029 Uiso 1 1 calc R U . . .
O3 O -0.0645(3) 0.35133(15) 0.21771(19) 0.0278(6) Uani 1 1 d . . . . .
C3 C -0.1142(5) 0.4137(2) 0.0585(3) 0.0237(8) Uani 1 1 d . . . . .
C3' C -0.0030(5) 0.5459(2) -0.2501(3) 0.0242(8) Uani 1 1 d . . . . .
O4 O 0.0599(4) 0.42962(16) 0.3756(2) 0.0262(6) Uani 1 1 d . . . . .
C4 C -0.0612(5) 0.4118(2) 0.1666(3) 0.0213(8) Uani 1 1 d . . . . .
C4' C -0.1437(5) 0.5101(2) -0.3133(3) 0.0234(8) Uani 1 1 d . . . . .
C4A C 0.0011(5) 0.4844(2) 0.2104(3) 0.0196(7) Uani 1 1 d . . . . .
H4OO H 0.029(7) 0.384(4) 0.336(4) 0.072(17) Uiso 1 1 d . . . . .
O5 O 0.1443(3) 0.56984(15) 0.45871(17) 0.0234(6) Uani 1 1 d . . . . .
C5 C 0.0569(5) 0.4922(2) 0.3151(3) 0.0201(7) Uani 1 1 d . . . . .
C5' C -0.2731(5) 0.4653(2) -0.2715(3) 0.0284(9) Uani 1 1 d . . . . .
H5' H -0.370605 0.442164 -0.313903 0.034 Uiso 1 1 calc R U . . .
O6 O 0.1627(3) 0.69510(14) 0.33787(18) 0.0239(6) Uani 1 1 d . . . . .
C6 C 0.1072(5) 0.5629(2) 0.3553(3) 0.0206(7) Uani 1 1 d . . . . .
C6' C -0.2624(5) 0.4537(2) -0.1675(3) 0.0282(9) Uani 1 1 d . . . . .
H6' H -0.350525 0.421841 -0.139578 0.034 Uiso 1 1 calc R U . . .
O7 O 0.1158(3) 0.59004(16) -0.29944(19) 0.0295(6) Uani 1 1 d . . . . .
C7 C 0.1069(5) 0.6280(2) 0.2923(3) 0.0203(7) Uani 1 1 d . . . . .
O8 O -0.1576(4) 0.51940(16) -0.41541(19) 0.0292(6) Uani 1 1 d . . . . .
C8 C 0.0553(5) 0.6214(2) 0.1901(3) 0.0215(8) Uani 1 1 d . . . . .
H8 H 0.056229 0.665044 0.147248 0.026 Uiso 1 1 calc R U . . .
C8A C 0.0022(5) 0.5500(2) 0.1517(3) 0.0196(7) Uani 1 1 d . . . . .
H8O H -0.053(7) 0.537(3) -0.432(3) 0.049(14) Uiso 1 1 d . . . . .
O9 O 0.3829(3) 0.07816(14) 0.69962(18) 0.0228(5) Uani 1 1 d . . . . .
C9 C -0.0477(6) 0.2884(3) 0.0061(4) 0.0424(11) Uani 1 1 d . . . . .
H9A H 0.038913 0.302938 -0.042361 0.064 Uiso 1 1 calc R U . . .
H9B H -0.110217 0.240321 -0.015479 0.064 Uiso 1 1 calc R U . . .
H9C H 0.020333 0.281201 0.072576 0.064 Uiso 1 1 calc R U . . .
O10 O 0.5527(4) 0.18252(17) 0.9235(2) 0.0418(8) Uani 1 1 d . . . . .
C10 C 0.3375(5) 0.5780(2) 0.4942(3) 0.0293(9) Uani 1 1 d . . . . .
H10A H 0.407830 0.535548 0.468226 0.044 Uiso 1 1 calc R U . . .
H10B H 0.352324 0.576892 0.567937 0.044 Uiso 1 1 calc R U . . .
H10C H 0.383791 0.627122 0.470693 0.044 Uiso 1 1 calc R U . . .
O11 O 0.6263(4) 0.03304(17) 0.9813(2) 0.0346(7) Uani 1 1 d . . . . .
C11 C 0.1492(5) 0.7628(2) 0.2747(3) 0.0265(8) Uani 1 1 d . . . . .
H11A H 0.229425 0.756735 0.220519 0.040 Uiso 1 1 calc R U . . .
H11B H 0.188299 0.808158 0.315142 0.040 Uiso 1 1 calc R U . . .
H11C H 0.020702 0.769543 0.245762 0.040 Uiso 1 1 calc R U . . .
O12 O 0.6347(4) -0.11241(17) 0.9355(2) 0.0296(6) Uani 1 1 d . . . . .
C12 C 0.2539(6) 0.6328(3) -0.2389(3) 0.0401(11) Uani 1 1 d . . . . .
H12A H 0.321475 0.665781 -0.282270 0.060 Uiso 1 1 calc R U . . .
H12B H 0.340490 0.597126 -0.201989 0.060 Uiso 1 1 calc R U . . .
H12C H 0.194331 0.664873 -0.191144 0.060 Uiso 1 1 calc R U . . .
H12O H 0.656(6) -0.063(3) 0.976(3) 0.042(13) Uiso 1 1 d . . . . .
O13 O 0.5403(4) -0.22448(15) 0.79742(19) 0.0297(6) Uani 1 1 d . . . . .
C13' C 0.3559(5) 0.2116(2) 0.7210(3) 0.0225(8) Uani 1 1 d . . . . .
O14 O 0.3914(4) -0.18699(15) 0.61224(19) 0.0314(6) Uani 1 1 d . . . . .
C14 C 0.4174(5) 0.1374(2) 0.7656(3) 0.0224(8) Uani 1 1 d . . . . .
C14' C 0.2720(5) 0.2123(2) 0.6213(3) 0.0235(8) Uani 1 1 d . . . . .
H14' H 0.254346 0.165217 0.585329 0.028 Uiso 1 1 calc R U . . .
O15 O 0.1296(4) 0.28740(15) 0.47941(19) 0.0310(6) Uani 1 1 d . . . . .
C15 C 0.5023(5) 0.1231(2) 0.8594(3) 0.0257(8) Uani 1 1 d . . . . .
C15' C 0.2151(5) 0.2807(2) 0.5752(3) 0.0237(8) Uani 1 1 d . . . . .
O16 O 0.1946(4) 0.41885(16) 0.5813(2) 0.0324(7) Uani 1 1 d . . . . .
C16 C 0.5512(5) 0.0458(2) 0.8937(3) 0.0245(8) Uani 1 1 d . . . . .
C16' C 0.2432(5) 0.3506(2) 0.6263(3) 0.0242(8) Uani 1 1 d . . . . .
C16A C 0.5113(5) -0.0142(2) 0.8213(3) 0.0214(8) Uani 1 1 d . . . . .
H16O H 0.140(6) 0.413(3) 0.517(4) 0.040(13) Uiso 1 1 d . . . . .
C17 C 0.5538(5) -0.0926(2) 0.8439(3) 0.0228(8) Uani 1 1 d . . . . .
C17' C 0.3204(5) 0.3502(2) 0.7247(3) 0.0262(8) Uani 1 1 d . . . . .
H17' H 0.335651 0.397328 0.760805 0.031 Uiso 1 1 calc R U . . .
C18 C 0.5131(5) -0.1486(2) 0.7722(3) 0.0241(8) Uani 1 1 d . . . . .
C18' C 0.3764(5) 0.2815(2) 0.7718(3) 0.0281(8) Uani 1 1 d . . . . .
H18' H 0.429574 0.282295 0.839736 0.034 Uiso 1 1 calc R U . . .
C19 C 0.4299(5) -0.1272(2) 0.6761(3) 0.0248(8) Uani 1 1 d . . . . .
C20 C 0.3882(5) -0.0508(2) 0.6518(3) 0.0239(8) Uani 1 1 d . . . . .
H20 H 0.332903 -0.036809 0.586881 0.029 Uiso 1 1 calc R U . . .
C20A C 0.4300(4) 0.0035(2) 0.7255(3) 0.0205(8) Uani 1 1 d . . . . .
C21 C 0.4351(9) 0.1903(4) 1.0035(4) 0.075(2) Uani 1 1 d . . . . .
H21A H 0.306318 0.196745 0.974882 0.113 Uiso 1 1 calc R U . . .
H21B H 0.473488 0.235435 1.044502 0.113 Uiso 1 1 calc R U . . .
H21C H 0.445470 0.144035 1.045735 0.113 Uiso 1 1 calc R U . . .
C22 C 0.6833(6) -0.2624(3) 0.7487(3) 0.0367(10) Uani 1 1 d . . . . .
H22A H 0.645958 -0.265685 0.676242 0.055 Uiso 1 1 calc R U . . .
H22B H 0.702708 -0.314371 0.776310 0.055 Uiso 1 1 calc R U . . .
H22C H 0.798661 -0.232927 0.760256 0.055 Uiso 1 1 calc R U . . .
C23 C 0.3353(6) -0.1691(3) 0.5093(3) 0.0341(10) Uani 1 1 d . . . . .
H23A H 0.427766 -0.135487 0.483216 0.051 Uiso 1 1 calc R U . . .
H23B H 0.215240 -0.142873 0.504167 0.051 Uiso 1 1 calc R U . . .
H23C H 0.324544 -0.216833 0.469929 0.051 Uiso 1 1 calc R U . . .
C24 C 0.0466(6) 0.2188(2) 0.4338(3) 0.0320(9) Uani 1 1 d . . . . .
H24A H -0.023546 0.232089 0.369582 0.048 Uiso 1 1 calc R U . . .
H24B H -0.036896 0.195898 0.478762 0.048 Uiso 1 1 calc R U . . .
H24C H 0.144007 0.181749 0.421968 0.048 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 C8A 1.364(4) . ?
O1 C2 1.371(4) . ?
C1' C6' 1.392(5) . ?
C1' C2' 1.406(5) . ?
C1' C2 1.470(5) . ?
O2 C3 1.372(4) . ?
O2 C9 1.428(5) . ?
C2 C3 1.356(5) . ?
C2' C3' 1.371(5) . ?
C2' H2' 0.9500 . ?
O3 C4 1.254(4) . ?
C3 C4 1.457(5) . ?
C3' O7 1.371(4) . ?
C3' C4' 1.402(5) . ?
O4 C5 1.353(4) . ?
O4 H4OO 0.97(6) . ?
C4 C4A 1.444(5) . ?
C4' O8 1.367(4) . ?
C4' C5' 1.380(5) . ?
C4A C8A 1.382(5) . ?
C4A C5 1.423(5) . ?
O5 C6 1.386(4) . ?
O5 C10 1.442(4) . ?
C5 C6 1.375(5) . ?
C5' C6' 1.398(5) . ?
C5' H5' 0.9500 . ?
O6 C7 1.357(4) . ?
O6 C11 1.445(4) . ?
C6 C7 1.410(5) . ?
C6' H6' 0.9500 . ?
O7 C12 1.430(4) . ?
C7 C8 1.384(5) . ?
O8 H8O 0.87(5) . ?
C8 C8A 1.382(5) . ?
C8 H8 0.9500 . ?
O9 C14 1.361(4) . ?
O9 C20A 1.375(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O10 C15 1.368(4) . ?
O10 C21 1.441(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O11 C16 1.260(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O12 C17 1.347(4) . ?
O12 H12O 1.02(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O13 C18 1.369(4) . ?
O13 C22 1.439(5) . ?
C13' C18' 1.391(5) . ?
C13' C14' 1.408(5) . ?
C13' C14 1.470(5) . ?
O14 C19 1.355(4) . ?
O14 C23 1.428(5) . ?
C14 C15 1.363(5) . ?
C14' C15' 1.383(5) . ?
C14' H14' 0.9500 . ?
O15 C15' 1.370(4) . ?
O15 C24 1.442(5) . ?
C15 C16 1.451(5) . ?
C15' C16' 1.397(5) . ?
O16 C16' 1.360(4) . ?
O16 H16O 0.92(5) . ?
C16 C16A 1.432(5) . ?
C16' C17' 1.377(5) . ?
C16A C20A 1.389(5) . ?
C16A C17 1.421(5) . ?
C17 C18 1.377(5) . ?
C17' C18' 1.390(5) . ?
C17' H17' 0.9500 . ?
C18 C19 1.412(5) . ?
C18' H18' 0.9500 . ?
C19 C20 1.391(5) . ?
C20 C20A 1.376(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C8A O1 C2 120.4(3) . . ?
C6' C1' C2' 119.5(3) . . ?
C6' C1' C2 123.1(3) . . ?
C2' C1' C2 117.4(3) . . ?
C3 O2 C9 114.1(3) . . ?
C3 C2 O1 121.2(3) . . ?
C3 C2 C1' 128.5(3) . . ?
O1 C2 C1' 110.2(3) . . ?
C3' C2' C1' 120.3(3) . . ?
C3' C2' H2' 119.9 . . ?
C1' C2' H2' 119.9 . . ?
C2 C3 O2 119.8(3) . . ?
C2 C3 C4 121.3(3) . . ?
O2 C3 C4 119.0(3) . . ?
C2' C3' O7 125.1(3) . . ?
C2' C3' C4' 120.5(3) . . ?
O7 C3' C4' 114.4(3) . . ?
C5 O4 H4OO 110(3) . . ?
O3 C4 C4A 122.2(3) . . ?
O3 C4 C3 122.8(3) . . ?
C4A C4 C3 115.0(3) . . ?
O8 C4' C5' 119.0(3) . . ?
O8 C4' C3' 121.7(3) . . ?
C5' C4' C3' 119.3(3) . . ?
C8A C4A C5 117.5(3) . . ?
C8A C4A C4 120.6(3) . . ?
C5 C4A C4 121.8(3) . . ?
C6 O5 C10 114.9(3) . . ?
O4 C5 C6 119.7(3) . . ?
O4 C5 C4A 119.8(3) . . ?
C6 C5 C4A 120.5(3) . . ?
C4' C5' C6' 120.8(3) . . ?
C4' C5' H5' 119.6 . . ?
C6' C5' H5' 119.6 . . ?
C7 O6 C11 115.9(3) . . ?
C5 C6 O5 119.0(3) . . ?
C5 C6 C7 119.9(3) . . ?
O5 C6 C7 120.9(3) . . ?
C1' C6' C5' 119.6(4) . . ?
C1' C6' H6' 120.2 . . ?
C5' C6' H6' 120.2 . . ?
C3' O7 C12 117.2(3) . . ?
O6 C7 C8 123.6(3) . . ?
O6 C7 C6 116.0(3) . . ?
C8 C7 C6 120.4(3) . . ?
C4' O8 H8O 109(3) . . ?
C8A C8 C7 118.6(3) . . ?
C8A C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
O1 C8A C4A 121.3(3) . . ?
O1 C8A C8 115.6(3) . . ?
C4A C8A C8 123.1(3) . . ?
C14 O9 C20A 121.6(3) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 O10 C21 113.3(4) . . ?
O5 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 C11 H11A 109.5 . . ?
O6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 O12 H12O 107(2) . . ?
O7 C12 H12A 109.5 . . ?
O7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 O13 C22 114.9(3) . . ?
C18' C13' C14' 118.0(3) . . ?
C18' C13' C14 123.6(3) . . ?
C14' C13' C14 118.4(3) . . ?
C19 O14 C23 117.4(3) . . ?
O9 C14 C15 119.6(3) . . ?
O9 C14 C13' 111.8(3) . . ?
C15 C14 C13' 128.6(4) . . ?
C15' C14' C13' 120.6(3) . . ?
C15' C14' H14' 119.7 . . ?
C13' C14' H14' 119.7 . . ?
C15' O15 C24 117.1(3) . . ?
C14 C15 O10 120.4(4) . . ?
C14 C15 C16 122.2(3) . . ?
O10 C15 C16 117.3(3) . . ?
O15 C15' C14' 125.1(3) . . ?
O15 C15' C16' 114.4(3) . . ?
C14' C15' C16' 120.5(3) . . ?
C16' O16 H16O 113(3) . . ?
O11 C16 C16A 122.7(3) . . ?
O11 C16 C15 121.7(3) . . ?
C16A C16 C15 115.7(3) . . ?
O16 C16' C17' 119.3(3) . . ?
O16 C16' C15' 121.5(3) . . ?
C17' C16' C15' 119.2(4) . . ?
C20A C16A C17 118.2(3) . . ?
C20A C16A C16 120.0(3) . . ?
C17 C16A C16 121.9(3) . . ?
O12 C17 C18 119.7(3) . . ?
O12 C17 C16A 120.2(3) . . ?
C18 C17 C16A 120.1(3) . . ?
C16' C17' C18' 120.6(4) . . ?
C16' C17' H17' 119.7 . . ?
C18' C17' H17' 119.7 . . ?
O13 C18 C17 119.5(3) . . ?
O13 C18 C19 121.0(3) . . ?
C17 C18 C19 119.2(3) . . ?
C17' C18' C13' 121.1(3) . . ?
C17' C18' H18' 119.5 . . ?
C13' C18' H18' 119.5 . . ?
O14 C19 C20 123.8(3) . . ?
O14 C19 C18 114.4(3) . . ?
C20 C19 C18 121.8(3) . . ?
C20A C20 C19 117.4(3) . . ?
C20A C20 H20 121.3 . . ?
C19 C20 H20 121.3 . . ?
O9 C20A C20 115.8(3) . . ?
O9 C20A C16A 120.8(3) . . ?
C20 C20A C16A 123.3(3) . . ?
O10 C21 H21A 109.5 . . ?
O10 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O10 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O13 C22 H22A 109.5 . . ?
O13 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O13 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O14 C23 H23A 109.5 . . ?
O14 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O14 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O15 C24 H24A 109.5 . . ?
O15 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O15 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C8A O1 C2 C3 4.9(5) . . . . ?
C8A O1 C2 C1' -172.1(3) . . . . ?
C6' C1' C2 C3 42.3(6) . . . . ?
C2' C1' C2 C3 -136.8(4) . . . . ?
C6' C1' C2 O1 -141.0(4) . . . . ?
C2' C1' C2 O1 39.9(4) . . . . ?
C6' C1' C2' C3' -1.0(6) . . . . ?
C2 C1' C2' C3' 178.2(3) . . . . ?
O1 C2 C3 O2 173.9(3) . . . . ?
C1' C2 C3 O2 -9.7(6) . . . . ?
O1 C2 C3 C4 -5.4(5) . . . . ?
C1' C2 C3 C4 171.0(3) . . . . ?
C9 O2 C3 C2 111.2(4) . . . . ?
C9 O2 C3 C4 -69.5(4) . . . . ?
C1' C2' C3' O7 -179.9(4) . . . . ?
C1' C2' C3' C4' 0.7(6) . . . . ?
C2 C3 C4 O3 -176.3(3) . . . . ?
O2 C3 C4 O3 4.4(5) . . . . ?
C2 C3 C4 C4A 1.9(5) . . . . ?
O2 C3 C4 C4A -177.4(3) . . . . ?
C2' C3' C4' O8 179.6(3) . . . . ?
O7 C3' C4' O8 0.2(5) . . . . ?
C2' C3' C4' C5' 0.6(6) . . . . ?
O7 C3' C4' C5' -178.9(3) . . . . ?
O3 C4 C4A C8A -179.8(3) . . . . ?
C3 C4 C4A C8A 2.0(4) . . . . ?
O3 C4 C4A C5 -2.1(5) . . . . ?
C3 C4 C4A C5 179.7(3) . . . . ?
C8A C4A C5 O4 -179.4(3) . . . . ?
C4 C4A C5 O4 2.9(5) . . . . ?
C8A C4A C5 C6 0.8(5) . . . . ?
C4 C4A C5 C6 -176.9(3) . . . . ?
O8 C4' C5' C6' 179.2(3) . . . . ?
C3' C4' C5' C6' -1.7(6) . . . . ?
O4 C5 C6 O5 -5.7(5) . . . . ?
C4A C5 C6 O5 174.1(3) . . . . ?
O4 C5 C6 C7 179.1(3) . . . . ?
C4A C5 C6 C7 -1.1(5) . . . . ?
C10 O5 C6 C5 106.4(4) . . . . ?
C10 O5 C6 C7 -78.5(4) . . . . ?
C2' C1' C6' C5' -0.1(6) . . . . ?
C2 C1' C6' C5' -179.2(4) . . . . ?
C4' C5' C6' C1' 1.4(6) . . . . ?
C2' C3' O7 C12 -4.1(5) . . . . ?
C4' C3' O7 C12 175.3(3) . . . . ?
C11 O6 C7 C8 5.7(5) . . . . ?
C11 O6 C7 C6 -175.6(3) . . . . ?
C5 C6 C7 O6 -178.5(3) . . . . ?
O5 C6 C7 O6 6.4(5) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
O5 C6 C7 C8 -174.8(3) . . . . ?
O6 C7 C8 C8A 179.4(3) . . . . ?
C6 C7 C8 C8A 0.8(5) . . . . ?
C2 O1 C8A C4A -0.8(5) . . . . ?
C2 O1 C8A C8 178.6(3) . . . . ?
C5 C4A C8A O1 179.6(3) . . . . ?
C4 C4A C8A O1 -2.6(5) . . . . ?
C5 C4A C8A C8 0.3(5) . . . . ?
C4 C4A C8A C8 178.0(3) . . . . ?
C7 C8 C8A O1 179.6(3) . . . . ?
C7 C8 C8A C4A -1.1(5) . . . . ?
C20A O9 C14 C15 0.7(5) . . . . ?
C20A O9 C14 C13' 179.7(3) . . . . ?
C18' C13' C14 O9 -179.3(3) . . . . ?
C14' C13' C14 O9 0.5(4) . . . . ?
C18' C13' C14 C15 -0.3(6) . . . . ?
C14' C13' C14 C15 179.5(3) . . . . ?
C18' C13' C14' C15' 1.1(5) . . . . ?
C14 C13' C14' C15' -178.7(3) . . . . ?
O9 C14 C15 O10 174.2(3) . . . . ?
C13' C14 C15 O10 -4.6(6) . . . . ?
O9 C14 C15 C16 -2.6(5) . . . . ?
C13' C14 C15 C16 178.5(3) . . . . ?
C21 O10 C15 C14 106.1(4) . . . . ?
C21 O10 C15 C16 -76.9(4) . . . . ?
C24 O15 C15' C14' 18.3(5) . . . . ?
C24 O15 C15' C16' -161.8(3) . . . . ?
C13' C14' C15' O15 -178.8(3) . . . . ?
C13' C14' C15' C16' 1.2(5) . . . . ?
C14 C15 C16 O11 -178.5(3) . . . . ?
O10 C15 C16 O11 4.5(5) . . . . ?
C14 C15 C16 C16A 2.4(5) . . . . ?
O10 C15 C16 C16A -174.6(3) . . . . ?
O15 C15' C16' O16 -2.4(5) . . . . ?
C14' C15' C16' O16 177.5(3) . . . . ?
O15 C15' C16' C17' 177.1(3) . . . . ?
C14' C15' C16' C17' -3.0(5) . . . . ?
O11 C16 C16A C20A -179.3(3) . . . . ?
C15 C16 C16A C20A -0.3(5) . . . . ?
O11 C16 C16A C17 0.2(5) . . . . ?
C15 C16 C16A C17 179.2(3) . . . . ?
C20A C16A C17 O12 179.2(3) . . . . ?
C16 C16A C17 O12 -0.3(5) . . . . ?
C20A C16A C17 C18 -0.5(5) . . . . ?
C16 C16A C17 C18 180.0(3) . . . . ?
O16 C16' C17' C18' -178.1(3) . . . . ?
C15' C16' C17' C18' 2.4(5) . . . . ?
C22 O13 C18 C17 -113.7(4) . . . . ?
C22 O13 C18 C19 71.5(4) . . . . ?
O12 C17 C18 O13 5.8(5) . . . . ?
C16A C17 C18 O13 -174.5(3) . . . . ?
O12 C17 C18 C19 -179.4(3) . . . . ?
C16A C17 C18 C19 0.3(5) . . . . ?
C16' C17' C18' C13' 0.0(5) . . . . ?
C14' C13' C18' C17' -1.7(5) . . . . ?
C14 C13' C18' C17' 178.1(3) . . . . ?
C23 O14 C19 C20 11.5(5) . . . . ?
C23 O14 C19 C18 -170.1(3) . . . . ?
O13 C18 C19 O14 -3.5(5) . . . . ?
C17 C18 C19 O14 -178.3(3) . . . . ?
O13 C18 C19 C20 174.9(3) . . . . ?
C17 C18 C19 C20 0.1(5) . . . . ?
O14 C19 C20 C20A 177.9(3) . . . . ?
C18 C19 C20 C20A -0.4(5) . . . . ?
C14 O9 C20A C20 -179.8(3) . . . . ?
C14 O9 C20A C16A 1.4(4) . . . . ?
C19 C20 C20A O9 -178.5(3) . . . . ?
C19 C20 C20A C16A 0.2(5) . . . . ?
C17 C16A C20A O9 178.9(3) . . . . ?
C16 C16A C20A O9 -1.5(5) . . . . ?
C17 C16A C20A C20 0.2(5) . . . . ?
C16 C16A C20A C20 179.8(3) . . . . ?

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
O4 H4OO O3 0.97(6) 1.75(5) 2.594(4) 144(5) .
O8 H8O O5 0.87(5) 2.22(5) 3.023(4) 154(4) 1_554
O8 H8O O7 0.87(5) 2.25(5) 2.688(3) 111(4) .
O12 H12O O11 1.02(5) 1.68(5) 2.601(4) 148(4) .
O16 H16O O4 0.92(5) 1.94(5) 2.829(4) 163(4) .

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        
'plant Crepis sancta, family Asteraceae, collected Southern Jordan'
