# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cu_20180878-asb-2i2_0m
_database_code_depnum_ccdc_archive 'CCDC 2009601'
loop_
_audit_author_name
_audit_author_address
'Zhang panpan'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2020-06-13 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        prieurianin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H50 O16'
_chemical_formula_sum            'C38 H50 O16'
_chemical_formula_weight         762.78

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

_cell_length_a                   11.0475(4)
_cell_length_b                   11.8932(4)
_cell_length_c                   29.2814(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3847.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       columnar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.864
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21645
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         4.012
_diffrn_reflns_theta_max         69.268
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             6880
_reflns_number_gt                6127
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.933
_reflns_Friedel_fraction_full    0.959

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2268 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6880
_refine_ls_number_parameters     495
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.002
_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 -0.3894(2) 1.05794(18) -0.45510(7) 0.0324(5) Uani 1 1 d . . . . .
O2 O -0.0018(2) 0.98513(19) -0.41724(7) 0.0344(5) Uani 1 1 d . . . . .
H2 H 0.0231 0.9583 -0.3932 0.052 Uiso 1 1 d R U . . .
O3 O -0.4745(2) 0.9259(2) -0.36001(8) 0.0353(5) Uani 1 1 d . . . . .
O4 O -0.2268(2) 1.07972(18) -0.52561(7) 0.0313(5) Uani 1 1 d . . . . .
O5 O -0.0757(3) 0.7104(2) -0.30331(8) 0.0444(6) Uani 1 1 d . . . . .
O6 O 0.0804(2) 0.9332(2) -0.32849(8) 0.0447(6) Uani 1 1 d . . . . .
O7 O 0.0730(2) 0.9927(2) -0.25648(8) 0.0464(6) Uani 1 1 d . . . . .
O8 O 0.1118(2) 0.7520(2) -0.44163(9) 0.0514(7) Uani 1 1 d . . . . .
O9 O -0.5288(2) 0.9276(2) -0.47435(11) 0.0569(7) Uani 1 1 d . . . . .
O10 O -0.1942(3) 1.2564(2) -0.50125(10) 0.0553(7) Uani 1 1 d . . . . .
O11 O 0.0834(3) 0.7226(2) -0.25585(10) 0.0570(7) Uani 1 1 d . . . . .
O12 O -0.3242(3) 0.8772(2) -0.26310(8) 0.0459(6) Uani 1 1 d . . . . .
O13 O 0.0770(3) 1.1726(3) -0.61172(9) 0.0577(8) Uani 1 1 d . . . . .
O14 O -0.6303(3) 1.0448(3) -0.36033(12) 0.0651(9) Uani 1 1 d . . . . .
O15 O -0.2770(3) 1.3443(2) -0.57763(11) 0.0661(9) Uani 1 1 d . . . . .
H15 H -0.2412 1.3758 -0.5986 0.099 Uiso 1 1 d R U . . .
O16 O -0.4955(4) 0.9502(4) -0.24193(11) 0.0816(11) Uani 1 1 d . . . . .
C1 C -0.5016(3) 1.0213(3) -0.46556(11) 0.0391(8) Uani 1 1 d . . . . .
H1 H -0.5632 1.0746 -0.4659 0.047 Uiso 1 1 calc R U . . .
C2 C -0.2226(3) 1.1924(3) -0.53077(11) 0.0348(7) Uani 1 1 d . . . . .
C3 C -0.1541(3) 0.8382(3) -0.42494(10) 0.0288(6) Uani 1 1 d . . . . .
C4 C -0.1847(3) 1.0351(3) -0.48256(10) 0.0287(6) Uani 1 1 d . . . . .
H4 H -0.1552 1.0962 -0.4630 0.034 Uiso 1 1 calc R U . . .
C5 C -0.0470(3) 0.8967(3) -0.44600(10) 0.0296(7) Uani 1 1 d . . . . .
C6 C 0.0715(3) 0.8359(3) -0.45894(11) 0.0373(7) Uani 1 1 d . . . . .
C7 C -0.0822(3) 0.9509(3) -0.49207(10) 0.0297(6) Uani 1 1 d . . . . .
C8 C -0.2631(3) 0.9143(3) -0.41364(9) 0.0273(6) Uani 1 1 d . . . . .
H8 H -0.3308 0.8621 -0.4093 0.033 Uiso 1 1 calc R U . . .
C9 C -0.1614(3) 0.7276(3) -0.42353(11) 0.0346(7) Uani 1 1 d . . . . .
H9A H -0.0995 0.6840 -0.4357 0.042 Uiso 1 1 calc R U . . .
H9B H -0.2284 0.6933 -0.4103 0.042 Uiso 1 1 calc R U . . .
C10 C -0.2919(3) 0.9754(3) -0.45954(9) 0.0284(6) Uani 1 1 d . . . . .
H10 H -0.3203 0.9178 -0.4809 0.034 Uiso 1 1 calc R U . . .
C11 C 0.0237(3) 0.9703(3) -0.29666(11) 0.0365(7) Uani 1 1 d . . . . .
C12 C 0.0403(4) 0.6919(3) -0.29145(14) 0.0467(9) Uani 1 1 d . . . . .
C13 C -0.1231(3) 0.8591(3) -0.52589(10) 0.0332(7) Uani 1 1 d . . . . .
H13A H -0.1865 0.8152 -0.5123 0.050 Uiso 1 1 calc R U . . .
H13B H -0.0558 0.8112 -0.5330 0.050 Uiso 1 1 calc R U . . .
H13C H -0.1524 0.8937 -0.5534 0.050 Uiso 1 1 calc R U . . .
C14 C -0.3989(3) 1.0502(3) -0.30122(12) 0.0420(8) Uani 1 1 d . . . . .
H14A H -0.3270 1.0927 -0.2933 0.050 Uiso 1 1 calc R U . . .
H14B H -0.4678 1.0998 -0.2975 0.050 Uiso 1 1 calc R U . . .
C15 C 0.0721(4) 1.1560(3) -0.56550(13) 0.0478(9) Uani 1 1 d . . . . .
H15A H 0.0824 1.2126 -0.5439 0.057 Uiso 1 1 calc R U . . .
C16 C -0.3904(3) 1.0175(3) -0.35180(10) 0.0332(7) Uani 1 1 d . . . . .
H16 H -0.4180 1.0822 -0.3698 0.040 Uiso 1 1 calc R U . . .
C17 C 0.0415(3) 1.0030(3) -0.50708(11) 0.0343(7) Uani 1 1 d . . . . .
H17 H 0.0586 1.0659 -0.4865 0.041 Uiso 1 1 calc R U . . .
C18 C -0.2078(3) 1.1070(3) -0.37649(11) 0.0350(7) Uani 1 1 d . . . . .
H18A H -0.1220 1.1014 -0.3813 0.053 Uiso 1 1 calc R U . . .
H18B H -0.2233 1.1541 -0.3505 0.053 Uiso 1 1 calc R U . . .
H18C H -0.2452 1.1390 -0.4031 0.053 Uiso 1 1 calc R U . . .
C19 C -0.3217(3) 0.7412(3) -0.32403(12) 0.0413(8) Uani 1 1 d . . . . .
H19A H -0.3669 0.6994 -0.3018 0.062 Uiso 1 1 calc R U . . .
H19B H -0.2682 0.6913 -0.3401 0.062 Uiso 1 1 calc R U . . .
H19C H -0.3764 0.7756 -0.3453 0.062 Uiso 1 1 calc R U . . .
C20 C -0.2606(3) 0.9887(3) -0.36776(10) 0.0286(6) Uani 1 1 d . . . . .
C21 C -0.5922(3) 0.9511(3) -0.36434(12) 0.0437(8) Uani 1 1 d . . . . .
C22 C 0.0503(3) 1.0470(3) -0.55515(11) 0.0360(7) Uani 1 1 d . . . . .
C23 C -0.1850(3) 0.9234(3) -0.32997(10) 0.0308(7) Uani 1 1 d . . . . .
H23 H -0.1246 0.8813 -0.3475 0.037 Uiso 1 1 calc R U . . .
C24 C -0.1514(4) 0.7698(3) -0.27165(11) 0.0434(8) Uani 1 1 d . . . . .
H24A H -0.1038 0.8229 -0.2540 0.052 Uiso 1 1 calc R U . . .
H24B H -0.1898 0.7176 -0.2507 0.052 Uiso 1 1 calc R U . . .
C25 C 0.1319(3) 0.9076(4) -0.49533(12) 0.0440(9) Uani 1 1 d . . . . .
H25A H 0.1493 0.8629 -0.5222 0.053 Uiso 1 1 calc R U . . .
H25B H 0.2071 0.9388 -0.4839 0.053 Uiso 1 1 calc R U . . .
C26 C -0.1084(3) 0.9994(3) -0.29792(11) 0.0363(7) Uani 1 1 d . . . . .
H26A H -0.1169 1.0769 -0.3078 0.044 Uiso 1 1 calc R U . . .
H26B H -0.1407 0.9940 -0.2672 0.044 Uiso 1 1 calc R U . . .
C27 C -0.2476(3) 0.8322(3) -0.30005(10) 0.0365(7) Uani 1 1 d . . . . .
C28 C 0.2032(4) 0.9711(4) -0.25241(15) 0.0556(11) Uani 1 1 d . . . . .
H28A H 0.2305 0.9935 -0.2226 0.083 Uiso 1 1 calc R U . . .
H28B H 0.2458 1.0134 -0.2752 0.083 Uiso 1 1 calc R U . . .
H28C H 0.2185 0.8924 -0.2567 0.083 Uiso 1 1 calc R U . . .
C29 C 0.0583(4) 1.0700(4) -0.63068(13) 0.0600(12) Uani 1 1 d . . . . .
H29 H 0.0564 1.0562 -0.6619 0.072 Uiso 1 1 calc R U . . .
C30 C 0.1048(4) 0.6301(4) -0.32827(16) 0.0604(11) Uani 1 1 d . . . . .
H30A H 0.0689 0.5572 -0.3321 0.091 Uiso 1 1 calc R U . . .
H30B H 0.1885 0.6216 -0.3201 0.091 Uiso 1 1 calc R U . . .
H30C H 0.0988 0.6715 -0.3563 0.091 Uiso 1 1 calc R U . . .
C31 C -0.2533(4) 1.2264(3) -0.57937(12) 0.0418(8) Uani 1 1 d . . . . .
H31 H -0.1811 1.2148 -0.5982 0.050 Uiso 1 1 calc R U . . .
C32 C -0.4114(4) 0.9548(4) -0.26754(11) 0.0474(9) Uani 1 1 d . . . . .
C33 C -0.4761(4) 1.1789(4) -0.57473(13) 0.0487(9) Uani 1 1 d . . . . .
H33A H -0.4611 1.1656 -0.5425 0.058 Uiso 1 1 calc R U . . .
H33B H -0.5009 1.2567 -0.5781 0.058 Uiso 1 1 calc R U . . .
C34 C 0.0429(4) 0.9910(4) -0.59853(12) 0.0509(10) Uani 1 1 d . . . . .
H34 H 0.0300 0.9147 -0.6034 0.061 Uiso 1 1 calc R U . . .
C35 C -0.3570(4) 1.1615(3) -0.60101(11) 0.0427(8) Uani 1 1 d . . . . .
H35 H -0.3368 1.0814 -0.5998 0.051 Uiso 1 1 calc R U . . .
C36 C -0.3687(5) 1.1947(5) -0.65110(14) 0.0704(14) Uani 1 1 d . . . . .
H36A H -0.3870 1.2734 -0.6533 0.106 Uiso 1 1 calc R U . . .
H36B H -0.4325 1.1519 -0.6650 0.106 Uiso 1 1 calc R U . . .
H36C H -0.2938 1.1796 -0.6666 0.106 Uiso 1 1 calc R U . . .
C37 C -0.5783(5) 1.1046(5) -0.5899(2) 0.0753(14) Uani 1 1 d . . . . .
H37A H -0.6489 1.1204 -0.5719 0.113 Uiso 1 1 calc R U . . .
H37B H -0.5557 1.0273 -0.5860 0.113 Uiso 1 1 calc R U . . .
H37C H -0.5957 1.1187 -0.6215 0.113 Uiso 1 1 calc R U . . .
C38 C -0.6661(4) 0.8484(4) -0.37411(17) 0.0626(12) Uani 1 1 d . . . . .
H38A H -0.6274 0.7837 -0.3610 0.094 Uiso 1 1 calc R U . . .
H38B H -0.6731 0.8384 -0.4065 0.094 Uiso 1 1 calc R U . . .
H38C H -0.7453 0.8571 -0.3611 0.094 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 C1 1.349(4) . ?
O1 C10 1.463(4) . ?
O2 C5 1.437(4) . ?
O2 H2 0.8200 . ?
O3 C21 1.340(5) . ?
O3 C16 1.452(4) . ?
O4 C2 1.350(4) . ?
O4 C4 1.444(3) . ?
O5 C12 1.345(5) . ?
O5 C24 1.435(4) . ?
O6 C11 1.206(4) . ?
O7 C11 1.323(4) . ?
O7 C28 1.466(5) . ?
O8 C6 1.204(4) . ?
O9 C1 1.182(5) . ?
O10 C2 1.193(4) . ?
O11 C12 1.203(5) . ?
O12 C32 1.341(5) . ?
O12 C27 1.474(4) . ?
O13 C29 1.357(6) . ?
O13 C15 1.369(5) . ?
O14 C21 1.197(5) . ?
O15 C31 1.427(5) . ?
O15 H15 0.8202 . ?
O16 C32 1.196(5) . ?
C1 H1 0.9300 . ?
C2 C31 1.518(5) . ?
C3 C9 1.318(5) . ?
C3 C5 1.505(4) . ?
C3 C8 1.542(4) . ?
C4 C10 1.536(4) . ?
C4 C7 1.538(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.543(4) . ?
C5 C7 1.545(4) . ?
C6 C25 1.519(5) . ?
C7 C13 1.542(4) . ?
C7 C17 1.563(4) . ?
C8 C10 1.561(4) . ?
C8 C20 1.609(4) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C10 H10 0.9800 . ?
C11 C26 1.500(5) . ?
C12 C30 1.487(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C32 1.509(5) . ?
C14 C16 1.534(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C22 1.352(5) . ?
C15 H15A 0.9300 . ?
C16 C20 1.547(5) . ?
C16 H16 0.9800 . ?
C17 C22 1.505(4) . ?
C17 C25 1.550(5) . ?
C17 H17 0.9800 . ?
C18 C20 1.544(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C27 1.528(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C23 1.589(4) . ?
C21 C38 1.497(6) . ?
C22 C34 1.437(5) . ?
C23 C26 1.554(4) . ?
C23 C27 1.556(4) . ?
C23 H23 0.9800 . ?
C24 C27 1.540(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C34 1.341(6) . ?
C29 H29 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C35 1.520(6) . ?
C31 H31 0.9800 . ?
C33 C37 1.501(6) . ?
C33 C35 1.537(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34 0.9300 . ?
C35 C36 1.524(5) . ?
C35 H35 0.9800 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 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 C10 116.1(3) . . ?
C5 O2 H2 109.5 . . ?
C21 O3 C16 118.0(3) . . ?
C2 O4 C4 116.8(2) . . ?
C12 O5 C24 117.9(3) . . ?
C11 O7 C28 116.1(3) . . ?
C32 O12 C27 126.2(3) . . ?
C29 O13 C15 105.6(3) . . ?
C31 O15 H15 109.5 . . ?
O9 C1 O1 125.9(3) . . ?
O9 C1 H1 117.0 . . ?
O1 C1 H1 117.0 . . ?
O10 C2 O4 124.1(3) . . ?
O10 C2 C31 124.6(3) . . ?
O4 C2 C31 111.2(3) . . ?
C9 C3 C5 121.5(3) . . ?
C9 C3 C8 122.1(3) . . ?
C5 C3 C8 115.5(3) . . ?
O4 C4 C10 107.7(2) . . ?
O4 C4 C7 108.5(2) . . ?
C10 C4 C7 110.2(2) . . ?
O4 C4 H4 110.1 . . ?
C10 C4 H4 110.1 . . ?
C7 C4 H4 110.1 . . ?
O2 C5 C3 111.8(2) . . ?
O2 C5 C6 101.1(2) . . ?
C3 C5 C6 123.4(3) . . ?
O2 C5 C7 107.1(2) . . ?
C3 C5 C7 110.7(3) . . ?
C6 C5 C7 101.2(2) . . ?
O8 C6 C25 126.7(3) . . ?
O8 C6 C5 126.8(3) . . ?
C25 C6 C5 106.4(3) . . ?
C4 C7 C13 111.2(3) . . ?
C4 C7 C5 107.4(2) . . ?
C13 C7 C5 109.8(3) . . ?
C4 C7 C17 115.9(3) . . ?
C13 C7 C17 110.9(2) . . ?
C5 C7 C17 101.0(2) . . ?
C3 C8 C10 104.4(2) . . ?
C3 C8 C20 119.2(2) . . ?
C10 C8 C20 117.8(2) . . ?
C3 C8 H8 104.6 . . ?
C10 C8 H8 104.6 . . ?
C20 C8 H8 104.6 . . ?
C3 C9 H9A 120.0 . . ?
C3 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
O1 C10 C4 107.2(2) . . ?
O1 C10 C8 112.7(2) . . ?
C4 C10 C8 115.8(2) . . ?
O1 C10 H10 106.9 . . ?
C4 C10 H10 106.9 . . ?
C8 C10 H10 106.9 . . ?
O6 C11 O7 123.2(3) . . ?
O6 C11 C26 124.8(3) . . ?
O7 C11 C26 112.0(3) . . ?
O11 C12 O5 123.5(4) . . ?
O11 C12 C30 126.0(4) . . ?
O5 C12 C30 110.5(4) . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C32 C14 C16 116.5(3) . . ?
C32 C14 H14A 108.2 . . ?
C16 C14 H14A 108.2 . . ?
C32 C14 H14B 108.2 . . ?
C16 C14 H14B 108.2 . . ?
H14A C14 H14B 107.3 . . ?
C22 C15 O13 111.5(3) . . ?
C22 C15 H15A 124.2 . . ?
O13 C15 H15A 124.2 . . ?
O3 C16 C14 108.1(3) . . ?
O3 C16 C20 112.2(2) . . ?
C14 C16 C20 113.9(3) . . ?
O3 C16 H16 107.5 . . ?
C14 C16 H16 107.5 . . ?
C20 C16 H16 107.5 . . ?
C22 C17 C25 114.9(3) . . ?
C22 C17 C7 117.2(3) . . ?
C25 C17 C7 102.2(3) . . ?
C22 C17 H17 107.3 . . ?
C25 C17 H17 107.3 . . ?
C7 C17 H17 107.3 . . ?
C20 C18 H18A 109.5 . . ?
C20 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C20 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C27 C19 H19A 109.5 . . ?
C27 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C27 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 C16 101.4(2) . . ?
C18 C20 C23 111.3(3) . . ?
C16 C20 C23 112.6(2) . . ?
C18 C20 C8 111.7(2) . . ?
C16 C20 C8 111.0(2) . . ?
C23 C20 C8 108.7(2) . . ?
O14 C21 O3 122.7(4) . . ?
O14 C21 C38 125.9(4) . . ?
O3 C21 C38 111.4(4) . . ?
C15 C22 C34 104.8(3) . . ?
C15 C22 C17 123.7(3) . . ?
C34 C22 C17 131.4(3) . . ?
C26 C23 C27 107.9(3) . . ?
C26 C23 C20 115.0(3) . . ?
C27 C23 C20 120.0(3) . . ?
C26 C23 H23 104.0 . . ?
C27 C23 H23 104.0 . . ?
C20 C23 H23 104.0 . . ?
O5 C24 C27 106.9(3) . . ?
O5 C24 H24A 110.3 . . ?
C27 C24 H24A 110.3 . . ?
O5 C24 H24B 110.3 . . ?
C27 C24 H24B 110.3 . . ?
H24A C24 H24B 108.6 . . ?
C6 C25 C17 106.5(3) . . ?
C6 C25 H25A 110.4 . . ?
C17 C25 H25A 110.4 . . ?
C6 C25 H25B 110.4 . . ?
C17 C25 H25B 110.4 . . ?
H25A C25 H25B 108.6 . . ?
C11 C26 C23 114.3(3) . . ?
C11 C26 H26A 108.7 . . ?
C23 C26 H26A 108.7 . . ?
C11 C26 H26B 108.7 . . ?
C23 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
O12 C27 C19 106.7(3) . . ?
O12 C27 C24 100.0(2) . . ?
C19 C27 C24 106.0(3) . . ?
O12 C27 C23 114.5(3) . . ?
C19 C27 C23 118.2(3) . . ?
C24 C27 C23 109.5(3) . . ?
O7 C28 H28A 109.5 . . ?
O7 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O7 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C34 C29 O13 111.2(3) . . ?
C34 C29 H29 124.4 . . ?
O13 C29 H29 124.4 . . ?
C12 C30 H30A 109.5 . . ?
C12 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C12 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O15 C31 C2 105.6(3) . . ?
O15 C31 C35 112.1(3) . . ?
C2 C31 C35 115.1(3) . . ?
O15 C31 H31 107.9 . . ?
C2 C31 H31 107.9 . . ?
C35 C31 H31 107.9 . . ?
O16 C32 O12 117.8(4) . . ?
O16 C32 C14 121.0(4) . . ?
O12 C32 C14 121.0(3) . . ?
C37 C33 C35 114.6(4) . . ?
C37 C33 H33A 108.6 . . ?
C35 C33 H33A 108.6 . . ?
C37 C33 H33B 108.6 . . ?
C35 C33 H33B 108.6 . . ?
H33A C33 H33B 107.6 . . ?
C29 C34 C22 106.8(4) . . ?
C29 C34 H34 126.6 . . ?
C22 C34 H34 126.6 . . ?
C31 C35 C36 109.5(4) . . ?
C31 C35 C33 111.6(3) . . ?
C36 C35 C33 112.0(3) . . ?
C31 C35 H35 107.9 . . ?
C36 C35 H35 107.9 . . ?
C33 C35 H35 107.9 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C33 C37 H37A 109.5 . . ?
C33 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C33 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C21 C38 H38A 109.5 . . ?
C21 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C21 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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 O1 C1 O9 6.3(5) . . . . ?
C4 O4 C2 O10 -5.1(5) . . . . ?
C4 O4 C2 C31 172.5(3) . . . . ?
C2 O4 C4 C10 117.9(3) . . . . ?
C2 O4 C4 C7 -122.8(3) . . . . ?
C9 C3 C5 O2 -132.9(3) . . . . ?
C8 C3 C5 O2 58.0(3) . . . . ?
C9 C3 C5 C6 -12.1(5) . . . . ?
C8 C3 C5 C6 178.8(3) . . . . ?
C9 C3 C5 C7 107.8(3) . . . . ?
C8 C3 C5 C7 -61.3(3) . . . . ?
O2 C5 C6 O8 98.5(4) . . . . ?
C3 C5 C6 O8 -27.2(5) . . . . ?
C7 C5 C6 O8 -151.4(4) . . . . ?
O2 C5 C6 C25 -77.3(3) . . . . ?
C3 C5 C6 C25 157.0(3) . . . . ?
C7 C5 C6 C25 32.8(3) . . . . ?
O4 C4 C7 C13 -54.8(3) . . . . ?
C10 C4 C7 C13 63.0(3) . . . . ?
O4 C4 C7 C5 -174.9(2) . . . . ?
C10 C4 C7 C5 -57.2(3) . . . . ?
O4 C4 C7 C17 73.1(3) . . . . ?
C10 C4 C7 C17 -169.2(2) . . . . ?
O2 C5 C7 C4 -62.9(3) . . . . ?
C3 C5 C7 C4 59.2(3) . . . . ?
C6 C5 C7 C4 -168.4(2) . . . . ?
O2 C5 C7 C13 176.0(2) . . . . ?
C3 C5 C7 C13 -61.9(3) . . . . ?
C6 C5 C7 C13 70.6(3) . . . . ?
O2 C5 C7 C17 58.9(3) . . . . ?
C3 C5 C7 C17 -179.0(2) . . . . ?
C6 C5 C7 C17 -46.5(3) . . . . ?
C9 C3 C8 C10 -115.0(3) . . . . ?
C5 C3 C8 C10 54.0(3) . . . . ?
C9 C3 C8 C20 110.9(3) . . . . ?
C5 C3 C8 C20 -80.1(3) . . . . ?
C1 O1 C10 C4 137.0(3) . . . . ?
C1 O1 C10 C8 -94.4(3) . . . . ?
O4 C4 C10 O1 -57.0(3) . . . . ?
C7 C4 C10 O1 -175.3(2) . . . . ?
O4 C4 C10 C8 176.2(2) . . . . ?
C7 C4 C10 C8 57.9(3) . . . . ?
C3 C8 C10 O1 -176.4(2) . . . . ?
C20 C8 C10 O1 -41.6(4) . . . . ?
C3 C8 C10 C4 -52.4(3) . . . . ?
C20 C8 C10 C4 82.4(3) . . . . ?
C28 O7 C11 O6 0.7(5) . . . . ?
C28 O7 C11 C26 -177.8(3) . . . . ?
C24 O5 C12 O11 0.0(5) . . . . ?
C24 O5 C12 C30 -179.7(3) . . . . ?
C29 O13 C15 C22 -0.4(5) . . . . ?
C21 O3 C16 C14 78.3(3) . . . . ?
C21 O3 C16 C20 -155.4(3) . . . . ?
C32 C14 C16 O3 39.9(4) . . . . ?
C32 C14 C16 C20 -85.5(4) . . . . ?
C4 C7 C17 C22 -74.8(4) . . . . ?
C13 C7 C17 C22 53.2(4) . . . . ?
C5 C7 C17 C22 169.5(3) . . . . ?
C4 C7 C17 C25 158.7(3) . . . . ?
C13 C7 C17 C25 -73.4(3) . . . . ?
C5 C7 C17 C25 43.0(3) . . . . ?
O3 C16 C20 C18 155.1(2) . . . . ?
C14 C16 C20 C18 -81.8(3) . . . . ?
O3 C16 C20 C23 -85.9(3) . . . . ?
C14 C16 C20 C23 37.2(4) . . . . ?
O3 C16 C20 C8 36.3(3) . . . . ?
C14 C16 C20 C8 159.4(3) . . . . ?
C3 C8 C20 C18 91.7(3) . . . . ?
C10 C8 C20 C18 -36.3(4) . . . . ?
C3 C8 C20 C16 -155.9(3) . . . . ?
C10 C8 C20 C16 76.1(3) . . . . ?
C3 C8 C20 C23 -31.4(4) . . . . ?
C10 C8 C20 C23 -159.5(3) . . . . ?
C16 O3 C21 O14 -2.3(5) . . . . ?
C16 O3 C21 C38 178.2(3) . . . . ?
O13 C15 C22 C34 0.9(5) . . . . ?
O13 C15 C22 C17 179.2(3) . . . . ?
C25 C17 C22 C15 -122.3(4) . . . . ?
C7 C17 C22 C15 117.7(4) . . . . ?
C25 C17 C22 C34 55.6(5) . . . . ?
C7 C17 C22 C34 -64.4(5) . . . . ?
C18 C20 C23 C26 21.0(4) . . . . ?
C16 C20 C23 C26 -92.2(3) . . . . ?
C8 C20 C23 C26 144.4(3) . . . . ?
C18 C20 C23 C27 152.3(3) . . . . ?
C16 C20 C23 C27 39.1(4) . . . . ?
C8 C20 C23 C27 -84.3(3) . . . . ?
C12 O5 C24 C27 151.0(3) . . . . ?
O8 C6 C25 C17 178.2(3) . . . . ?
C5 C6 C25 C17 -6.0(4) . . . . ?
C22 C17 C25 C6 -151.0(3) . . . . ?
C7 C17 C25 C6 -22.9(3) . . . . ?
O6 C11 C26 C23 32.6(5) . . . . ?
O7 C11 C26 C23 -148.9(3) . . . . ?
C27 C23 C26 C11 98.7(3) . . . . ?
C20 C23 C26 C11 -124.4(3) . . . . ?
C32 O12 C27 C19 -81.7(4) . . . . ?
C32 O12 C27 C24 168.1(4) . . . . ?
C32 O12 C27 C23 51.1(5) . . . . ?
O5 C24 C27 O12 174.0(3) . . . . ?
O5 C24 C27 C19 63.2(4) . . . . ?
O5 C24 C27 C23 -65.3(3) . . . . ?
C26 C23 C27 O12 57.1(4) . . . . ?
C20 C23 C27 O12 -77.1(3) . . . . ?
C26 C23 C27 C19 -175.7(3) . . . . ?
C20 C23 C27 C19 50.0(4) . . . . ?
C26 C23 C27 C24 -54.2(3) . . . . ?
C20 C23 C27 C24 171.5(3) . . . . ?
C15 O13 C29 C34 -0.4(5) . . . . ?
O10 C2 C31 O15 -17.3(5) . . . . ?
O4 C2 C31 O15 165.1(3) . . . . ?
O10 C2 C31 C35 -141.5(4) . . . . ?
O4 C2 C31 C35 41.0(4) . . . . ?
C27 O12 C32 O16 149.4(4) . . . . ?
C27 O12 C32 C14 -35.4(5) . . . . ?
C16 C14 C32 O16 -122.4(4) . . . . ?
C16 C14 C32 O12 62.5(5) . . . . ?
O13 C29 C34 C22 0.9(5) . . . . ?
C15 C22 C34 C29 -1.1(5) . . . . ?
C17 C22 C34 C29 -179.3(4) . . . . ?
O15 C31 C35 C36 65.6(4) . . . . ?
C2 C31 C35 C36 -173.6(3) . . . . ?
O15 C31 C35 C33 -58.9(4) . . . . ?
C2 C31 C35 C33 61.8(4) . . . . ?
C37 C33 C35 C31 -171.5(4) . . . . ?
C37 C33 C35 C36 65.3(5) . . . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.055



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/H2O (10:1)'
_chemical_compound_source        'Aphanamixis  sinensis'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_220191077_0m
_database_code_depnum_ccdc_archive 'CCDC 2009602'
loop_
_audit_author_name
_audit_author_address
'Zhang panpan'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2020-06-13 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;
_audit_creation_date             2019-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '12-Hydroxyzaphaprinin H'
_chemical_formula_moiety         'C27 H34 O10, H2 O'
_chemical_formula_sum            'C27 H36 O11'
_chemical_formula_weight         536.56
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

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

_cell_length_a                   11.6885(3)
_cell_length_b                   13.2860(4)
_cell_length_c                   16.7135(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2595.50(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    170
_cell_measurement_theta_max      72.336
_cell_measurement_theta_min      3.326
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.878
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1393 before and 0.0659 after correction. The Ratio of minimum to maximum transmission is 0.7917. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14196
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.339
_diffrn_reflns_theta_min         4.616
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                4706
_reflns_number_total             4959
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1919 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4959
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.6761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0985
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O10(H10A,H10B)
2.b Ternary CH refined with riding coordinates:
 C5(H5A), C11(H11), C9(H9A), C12(H12), C17(H17), C1(H1)
2.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B), C16(H16A,H16B), C29(H29A,H29B)
2.d Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C21(H21)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C28(H28A,H28B,H28C), C18(H18A,H18B,H18C), C24(H24A,H24B,
 H24C)
2.f Idealised tetrahedral OH refined as rotating group:
 O8(H8), O9(H9), O5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O3 O 0.39112(14) 0.65625(12) 0.50576(10) 0.0219(4) Uani 1 1 d . . . . .
O8 O 0.33036(17) 0.42913(13) 0.35498(11) 0.0286(4) Uani 1 1 d . . . . .
H8 H 0.302350 0.427468 0.308714 0.043 Uiso 1 1 calc GR . . . .
O9 O 0.29449(16) 0.61421(14) 0.27256(11) 0.0277(4) Uani 1 1 d . . . . .
H9 H 0.224536 0.599841 0.273896 0.042 Uiso 1 1 calc GR . . . .
O10 O 0.06940(17) 0.56938(15) 0.29912(12) 0.0336(4) Uani 1 1 d . . . . .
H10A H 0.018340 0.614792 0.310577 0.050 Uiso 1 1 d G . . . .
H10B H 0.063595 0.525375 0.337442 0.050 Uiso 1 1 d G . . . .
O2 O 0.28241(17) 0.70065(14) 0.73365(11) 0.0312(4) Uani 1 1 d . . . . .
O6 O 0.20563(17) 0.30296(13) 0.45826(11) 0.0308(4) Uani 1 1 d . . . . .
O7 O 0.07616(18) 0.40621(15) 0.40738(12) 0.0375(5) Uani 1 1 d . . . . .
O1 O 0.43122(19) 0.75710(15) 0.66293(13) 0.0403(5) Uani 1 1 d . . . . .
O4 O 0.60834(17) 0.79767(16) 0.51632(13) 0.0399(5) Uani 1 1 d . . . . .
O5 O 0.1684(2) 0.2844(2) 0.62211(13) 0.0541(7) Uani 1 1 d . . . . .
H5 H 0.185940 0.307786 0.667172 0.081 Uiso 1 1 calc GR . . . .
C3 C 0.3623(2) 0.69263(19) 0.67691(15) 0.0251(5) Uani 1 1 d . . . . .
C5 C 0.3221(2) 0.41729(18) 0.53720(15) 0.0256(5) Uani 1 1 d . . . . .
H5A H 0.313536 0.416374 0.596727 0.031 Uiso 1 1 calc R . . . .
C11 C 0.4062(2) 0.51191(19) 0.36135(14) 0.0247(5) Uani 1 1 d . . . . .
H11 H 0.457960 0.507706 0.313824 0.030 Uiso 1 1 calc R . . . .
O11 O 0.2480(3) 0.9682(2) 0.23309(18) 0.0795(10) Uani 1 1 d . . . . .
C9 C 0.4840(2) 0.49597(19) 0.43600(15) 0.0255(5) Uani 1 1 d . . . . .
H9A H 0.536121 0.438526 0.423211 0.031 Uiso 1 1 calc R . . . .
C12 C 0.3405(2) 0.61221(18) 0.35279(14) 0.0227(5) Uani 1 1 d . . . . .
H12 H 0.275475 0.612446 0.391684 0.027 Uiso 1 1 calc R . . . .
C7 C 0.1565(2) 0.39283(19) 0.45144(16) 0.0282(5) Uani 1 1 d . . . . .
C6 C 0.2109(2) 0.46648(18) 0.50773(16) 0.0255(5) Uani 1 1 d . . . . .
H6A H 0.159291 0.480665 0.553345 0.031 Uiso 1 1 calc R . . . .
H6B H 0.227613 0.530537 0.479822 0.031 Uiso 1 1 calc R . . . .
C17 C 0.3522(2) 0.80180(19) 0.39495(16) 0.0266(5) Uani 1 1 d . . . . .
H17 H 0.291727 0.781419 0.434020 0.032 Uiso 1 1 calc R . . . .
C20 C 0.2941(3) 0.8594(2) 0.33014(17) 0.0336(6) Uani 1 1 d . . . . .
C2 C 0.3511(2) 0.59271(19) 0.63522(15) 0.0274(5) Uani 1 1 d . . . . .
H2A H 0.270658 0.583531 0.618065 0.033 Uiso 1 1 calc R . . . .
H2B H 0.369588 0.538307 0.673565 0.033 Uiso 1 1 calc R . . . .
C1 C 0.4284(2) 0.58321(18) 0.56290(14) 0.0237(5) Uani 1 1 d . . . . .
H1 H 0.507328 0.602534 0.580136 0.028 Uiso 1 1 calc R . . . .
C30 C 0.6702(3) 0.5932(2) 0.43235(18) 0.0356(6) Uani 1 1 d . . . . .
C14 C 0.4811(2) 0.67942(19) 0.44787(15) 0.0250(5) Uani 1 1 d . . . . .
C8 C 0.5580(2) 0.5900(2) 0.43954(15) 0.0273(5) Uani 1 1 d . . . . .
C13 C 0.4167(2) 0.70348(19) 0.36959(14) 0.0236(5) Uani 1 1 d . . . . .
C22 C 0.1810(3) 0.8387(2) 0.30077(18) 0.0391(7) Uani 1 1 d . . . . .
H22 H 0.131355 0.786851 0.318841 0.047 Uiso 1 1 calc R . . . .
C19 C 0.5319(2) 0.4223(2) 0.57051(17) 0.0327(6) Uani 1 1 d . . . . .
H19A H 0.510415 0.418283 0.627105 0.049 Uiso 1 1 calc GR . . . .
H19B H 0.603608 0.459909 0.565253 0.049 Uiso 1 1 calc GR . . . .
H19C H 0.542155 0.354200 0.549127 0.049 Uiso 1 1 calc GR . . . .
C10 C 0.4363(2) 0.47670(18) 0.52323(15) 0.0246(5) Uani 1 1 d . . . . .
C15 C 0.5253(2) 0.7823(2) 0.47547(16) 0.0292(6) Uani 1 1 d . . . . .
C4 C 0.3055(3) 0.30387(19) 0.51224(16) 0.0320(6) Uani 1 1 d . . . . .
C28 C 0.3990(3) 0.2478(2) 0.4683(2) 0.0437(8) Uani 1 1 d . . . . .
H28A H 0.368876 0.183668 0.448447 0.066 Uiso 1 1 calc GR . . . .
H28B H 0.462850 0.234902 0.504930 0.066 Uiso 1 1 calc GR . . . .
H28C H 0.425848 0.288479 0.423170 0.066 Uiso 1 1 calc GR . . . .
C18 C 0.5012(2) 0.7242(2) 0.30153(16) 0.0318(6) Uani 1 1 d . . . . .
H18A H 0.539880 0.661457 0.286673 0.048 Uiso 1 1 calc GR . . . .
H18B H 0.558041 0.773597 0.319237 0.048 Uiso 1 1 calc GR . . . .
H18C H 0.459721 0.750686 0.255138 0.048 Uiso 1 1 calc GR . . . .
C16 C 0.4436(3) 0.8606(2) 0.44236(19) 0.0354(6) Uani 1 1 d . . . . .
H16A H 0.484581 0.908097 0.406886 0.042 Uiso 1 1 calc R . . . .
H16B H 0.407657 0.899119 0.486390 0.042 Uiso 1 1 calc R . . . .
C24 C 0.2857(3) 0.7924(2) 0.78058(18) 0.0398(7) Uani 1 1 d . . . . .
H24A H 0.286883 0.850706 0.744658 0.060 Uiso 1 1 calc GR . . . .
H24B H 0.354638 0.792752 0.813945 0.060 Uiso 1 1 calc GR . . . .
H24C H 0.217773 0.795804 0.814854 0.060 Uiso 1 1 calc GR . . . .
C29 C 0.2672(3) 0.2427(2) 0.58544(19) 0.0459(8) Uani 1 1 d . . . . .
H29A H 0.250642 0.172697 0.568705 0.055 Uiso 1 1 calc R . . . .
H29B H 0.330330 0.240531 0.624934 0.055 Uiso 1 1 calc R . . . .
C23 C 0.1587(4) 0.9058(3) 0.2433(2) 0.0570(11) Uani 1 1 d . . . . .
H23 H 0.089372 0.908941 0.213809 0.068 Uiso 1 1 calc R . . . .
C21 C 0.3307(4) 0.9392(3) 0.2877(3) 0.0648(11) Uani 1 1 d . . . . .
H21 H 0.402901 0.970955 0.294242 0.078 Uiso 1 1 calc R . . . .
H30A H 0.710(3) 0.656(2) 0.4364(18) 0.024(7) Uiso 1 1 d . . . . .
H30B H 0.715(3) 0.534(2) 0.4197(19) 0.027(7) Uiso 1 1 d . . . . .


_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
O3 C1 1.430(3) . ?
O3 C14 1.462(3) . ?
O8 H8 0.8400 . ?
O8 C11 1.417(3) . ?
O9 H9 0.8400 . ?
O9 C12 1.445(3) . ?
O10 H10A 0.8700 . ?
O10 H10B 0.8699 . ?
O2 C3 1.335(3) . ?
O2 C24 1.450(3) . ?
O6 C7 1.330(3) . ?
O6 C4 1.476(3) . ?
O7 C7 1.206(3) . ?
O1 C3 1.199(3) . ?
O4 C15 1.204(3) . ?
O5 H5 0.8400 . ?
O5 C29 1.420(5) . ?
C3 C2 1.505(3) . ?
C5 H5A 1.0000 . ?
C5 C6 1.536(4) . ?
C5 C10 1.568(4) . ?
C5 C4 1.576(3) . ?
C11 H11 1.0000 . ?
C11 C9 1.558(3) . ?
C11 C12 1.545(3) . ?
O11 C23 1.344(6) . ?
O11 C21 1.384(5) . ?
C9 H9A 1.0000 . ?
C9 C8 1.521(4) . ?
C9 C10 1.581(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.531(3) . ?
C7 C6 1.499(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C17 H17 1.0000 . ?
C17 C20 1.491(4) . ?
C17 C13 1.566(3) . ?
C17 C16 1.542(4) . ?
C20 C22 1.436(5) . ?
C20 C21 1.345(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.515(4) . ?
C1 H1 1.0000 . ?
C1 C10 1.566(3) . ?
C30 C8 1.318(4) . ?
C30 H30A 0.96(3) . ?
C30 H30B 0.97(3) . ?
C14 C8 1.497(4) . ?
C14 C13 1.543(3) . ?
C14 C15 1.533(4) . ?
C13 C18 1.531(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.336(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 C10 1.547(3) . ?
C15 C16 1.517(4) . ?
C4 C28 1.512(4) . ?
C4 C29 1.536(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C23 H23 0.9500 . ?
C21 H21 0.9500 . ?

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 O3 C14 111.47(18) . . ?
C11 O8 H8 109.5 . . ?
C12 O9 H9 109.5 . . ?
H10A O10 H10B 104.5 . . ?
C3 O2 C24 115.7(2) . . ?
C7 O6 C4 112.77(19) . . ?
C29 O5 H5 109.5 . . ?
O2 C3 C2 109.8(2) . . ?
O1 C3 O2 123.5(2) . . ?
O1 C3 C2 126.7(2) . . ?
C6 C5 H5A 103.9 . . ?
C6 C5 C10 117.3(2) . . ?
C6 C5 C4 102.6(2) . . ?
C10 C5 H5A 103.9 . . ?
C10 C5 C4 123.1(2) . . ?
C4 C5 H5A 103.9 . . ?
O8 C11 H11 106.0 . . ?
O8 C11 C9 108.6(2) . . ?
O8 C11 C12 110.6(2) . . ?
C9 C11 H11 106.0 . . ?
C12 C11 H11 106.0 . . ?
C12 C11 C9 118.8(2) . . ?
C23 O11 C21 106.6(3) . . ?
C11 C9 H9A 106.7 . . ?
C11 C9 C10 123.7(2) . . ?
C8 C9 C11 104.6(2) . . ?
C8 C9 H9A 106.7 . . ?
C8 C9 C10 107.3(2) . . ?
C10 C9 H9A 106.7 . . ?
O9 C12 C11 106.67(19) . . ?
O9 C12 H12 108.7 . . ?
O9 C12 C13 111.85(19) . . ?
C11 C12 H12 108.7 . . ?
C13 C12 C11 112.2(2) . . ?
C13 C12 H12 108.7 . . ?
O6 C7 C6 110.4(2) . . ?
O7 C7 O6 121.4(2) . . ?
O7 C7 C6 128.1(2) . . ?
C5 C6 H6A 110.4 . . ?
C5 C6 H6B 110.4 . . ?
C7 C6 C5 106.4(2) . . ?
C7 C6 H6A 110.4 . . ?
C7 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
C20 C17 H17 106.9 . . ?
C20 C17 C13 116.8(2) . . ?
C20 C17 C16 115.4(2) . . ?
C13 C17 H17 106.9 . . ?
C16 C17 H17 106.9 . . ?
C16 C17 C13 103.2(2) . . ?
C22 C20 C17 124.7(3) . . ?
C21 C20 C17 130.0(3) . . ?
C21 C20 C22 105.3(3) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C3 C2 C1 113.0(2) . . ?
H2A C2 H2B 107.8 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
O3 C1 C2 107.14(19) . . ?
O3 C1 H1 107.4 . . ?
O3 C1 C10 110.41(19) . . ?
C2 C1 H1 107.4 . . ?
C2 C1 C10 116.6(2) . . ?
C10 C1 H1 107.4 . . ?
C8 C30 H30A 120.3(18) . . ?
C8 C30 H30B 122.1(18) . . ?
H30A C30 H30B 117(2) . . ?
O3 C14 C8 109.06(19) . . ?
O3 C14 C13 104.72(19) . . ?
O3 C14 C15 103.4(2) . . ?
C8 C14 C13 112.2(2) . . ?
C8 C14 C15 122.2(2) . . ?
C15 C14 C13 103.6(2) . . ?
C30 C8 C9 126.1(3) . . ?
C30 C8 C14 125.5(3) . . ?
C14 C8 C9 108.3(2) . . ?
C12 C13 C17 115.5(2) . . ?
C12 C13 C14 105.98(19) . . ?
C12 C13 C18 112.4(2) . . ?
C14 C13 C17 100.2(2) . . ?
C18 C13 C17 111.2(2) . . ?
C18 C13 C14 110.6(2) . . ?
C20 C22 H22 126.4 . . ?
C23 C22 C20 107.3(3) . . ?
C23 C22 H22 126.4 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
C5 C10 C9 121.2(2) . . ?
C1 C10 C5 110.0(2) . . ?
C1 C10 C9 105.36(19) . . ?
C19 C10 C5 107.7(2) . . ?
C19 C10 C9 107.0(2) . . ?
C19 C10 C1 104.4(2) . . ?
O4 C15 C14 126.4(3) . . ?
O4 C15 C16 126.8(2) . . ?
C16 C15 C14 106.8(2) . . ?
O6 C4 C5 105.48(19) . . ?
O6 C4 C28 105.7(2) . . ?
O6 C4 C29 104.6(2) . . ?
C28 C4 C5 120.7(2) . . ?
C28 C4 C29 109.7(3) . . ?
C29 C4 C5 109.3(2) . . ?
C4 C28 H28A 109.5 . . ?
C4 C28 H28B 109.5 . . ?
C4 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C16 H16A 110.5 . . ?
C17 C16 H16B 110.5 . . ?
C15 C16 C17 106.1(2) . . ?
C15 C16 H16A 110.5 . . ?
C15 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C29 C4 112.0(3) . . ?
O5 C29 H29A 109.2 . . ?
O5 C29 H29B 109.2 . . ?
C4 C29 H29A 109.2 . . ?
C4 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
O11 C23 H23 124.7 . . ?
C22 C23 O11 110.6(4) . . ?
C22 C23 H23 124.7 . . ?
O11 C21 H21 124.9 . . ?
C20 C21 O11 110.2(4) . . ?
C20 C21 H21 124.9 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/H2O (10:1)'
_chemical_compound_source        'Aphanamixis  sinensis'
####################################################################### 
# 
# 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_22019688_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 2041196'
loop_
_audit_author_name
_audit_author_address
'Zhang panpan'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;
_audit_creation_date             2019-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H40 O11'
_chemical_formula_sum            'C32 H40 O11'
_chemical_formula_weight         600.64
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   13.8459(2)
_cell_length_b                   15.1850(2)
_cell_length_c                   31.6599(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6656.49(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9727
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.424
_cell_measurement_theta_min      2.792
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1651 before and 0.0680 after correction. The Ratio of minimum to maximum transmission is 0.7638. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2560
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            35605
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.410
_diffrn_reflns_theta_min         2.791
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                6348
_reflns_number_total             6551
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2768 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6551
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+5.5996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1022
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O6-H6
 0.85 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C9(H9), C1(H1), C17(H17), C5(H5), C2'(H2'), C3'(H3')
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C2(H2A,H2B), C29(H29A,H29B), C4'(H4'A,H4'B), C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C23(H23), C22(H22)
3.d X=CH2 refined with riding coordinates:
 C30(H30A,H30B)
3.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C28(H28A,H28B,H28C), C5'(H5'A,H5'B,
 H5'C), C6'(H6'A,H6'B,H6'C)
3.f Idealised tetrahedral OH refined as rotating group:
 O10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O6 O 0.59142(12) 0.47221(12) 0.10951(5) 0.0194(3) Uani 1 1 d D . . . .
O11 O 0.83512(12) 0.42941(11) 0.17680(5) 0.0176(3) Uani 1 1 d . . . . .
O5 O 0.82148(12) 0.28587(11) 0.13095(6) 0.0214(4) Uani 1 1 d . . . . .
O3 O 0.60973(13) 0.09594(12) 0.08687(6) 0.0232(4) Uani 1 1 d . . . . .
O9 O 0.89134(13) 0.50575(14) 0.12054(6) 0.0282(4) Uani 1 1 d . . . . .
O7 O 0.41004(13) 0.49582(14) 0.16938(6) 0.0279(4) Uani 1 1 d . . . . .
O10 O 1.04471(14) 0.56000(14) 0.16920(6) 0.0302(4) Uani 1 1 d . . . . .
H10 H 1.058313 0.558884 0.143352 0.045 Uiso 1 1 calc GR . . . .
O2 O 0.41889(13) 0.18589(14) 0.02377(6) 0.0286(4) Uani 1 1 d . . . . .
O4 O 0.91911(14) 0.19247(14) 0.10127(7) 0.0324(5) Uani 1 1 d . . . . .
O8 O 0.78328(17) 0.65246(15) 0.27427(7) 0.0381(5) Uani 1 1 d . . . . .
O1 O 0.31303(16) 0.29563(18) 0.02082(8) 0.0474(6) Uani 1 1 d . . . . .
C30 C 0.47304(19) 0.30284(18) 0.16548(8) 0.0254(5) Uani 1 1 d . . . . .
H30A H 0.425449 0.338660 0.178590 0.030 Uiso 1 1 calc R . . . .
H30B H 0.464175 0.240887 0.163920 0.030 Uiso 1 1 calc R . . . .
C8 C 0.55243(16) 0.33958(16) 0.14922(7) 0.0170(5) Uani 1 1 d . . . . .
C10 C 0.63833(16) 0.25680(15) 0.08500(7) 0.0159(4) Uani 1 1 d . . . . .
C18 C 0.64658(18) 0.41884(16) 0.22290(8) 0.0198(5) Uani 1 1 d . . . . .
H18A H 0.591057 0.447760 0.236170 0.030 Uiso 1 1 calc GR . . . .
H18B H 0.704679 0.429940 0.239758 0.030 Uiso 1 1 calc GR . . . .
H18C H 0.634852 0.355276 0.221317 0.030 Uiso 1 1 calc GR . . . .
C15 C 0.49705(18) 0.50258(18) 0.16892(8) 0.0206(5) Uani 1 1 d . . . . .
C14 C 0.57067(16) 0.43674(16) 0.15066(7) 0.0170(4) Uani 1 1 d . . . . .
C13 C 0.66090(16) 0.45565(15) 0.17825(7) 0.0166(4) Uani 1 1 d . . . . .
C19 C 0.69457(17) 0.32215(16) 0.05766(8) 0.0184(5) Uani 1 1 d . . . . .
H19A H 0.669458 0.381708 0.062295 0.028 Uiso 1 1 calc GR . . . .
H19B H 0.687169 0.306337 0.027824 0.028 Uiso 1 1 calc GR . . . .
H19C H 0.763099 0.320257 0.065345 0.028 Uiso 1 1 calc GR . . . .
C11 C 0.73324(16) 0.31181(15) 0.15284(7) 0.0161(4) Uani 1 1 d . . . . .
H11 H 0.737117 0.288659 0.182359 0.019 Uiso 1 1 calc R . . . .
C12 C 0.74486(16) 0.41220(15) 0.15489(7) 0.0150(4) Uani 1 1 d . . . . .
H12 H 0.748711 0.436391 0.125560 0.018 Uiso 1 1 calc R . . . .
C9 C 0.63515(16) 0.28051(15) 0.13360(7) 0.0158(4) Uani 1 1 d . . . . .
H9 H 0.622814 0.222714 0.147749 0.019 Uiso 1 1 calc R . . . .
C1 C 0.68290(17) 0.16186(16) 0.08164(8) 0.0186(5) Uani 1 1 d . . . . .
H1 H 0.712049 0.154925 0.052936 0.022 Uiso 1 1 calc R . . . .
C20 C 0.72592(18) 0.60067(16) 0.21216(8) 0.0218(5) Uani 1 1 d . . . . .
C16 C 0.55403(19) 0.58217(18) 0.18411(9) 0.0252(5) Uani 1 1 d . . . . .
H16A H 0.538568 0.595137 0.214001 0.030 Uiso 1 1 calc R . . . .
H16B H 0.538007 0.634565 0.166871 0.030 Uiso 1 1 calc R . . . .
C2 C 0.75955(18) 0.13818(16) 0.11473(9) 0.0220(5) Uani 1 1 d . . . . .
H2A H 0.729008 0.134916 0.142956 0.026 Uiso 1 1 calc R . . . .
H2B H 0.787035 0.079586 0.108132 0.026 Uiso 1 1 calc R . . . .
C17 C 0.66215(17) 0.55883(15) 0.17937(8) 0.0189(5) Uani 1 1 d . . . . .
H17 H 0.683968 0.580083 0.151040 0.023 Uiso 1 1 calc R . . . .
C28 C 0.5719(2) 0.19587(19) -0.00965(8) 0.0264(5) Uani 1 1 d . . . . .
H28A H 0.547351 0.154530 -0.030862 0.040 Uiso 1 1 calc GR . . . .
H28B H 0.641880 0.188409 -0.006738 0.040 Uiso 1 1 calc GR . . . .
H28C H 0.557718 0.256311 -0.018557 0.040 Uiso 1 1 calc GR . . . .
C3 C 0.83927(18) 0.20559(17) 0.11549(8) 0.0221(5) Uani 1 1 d . . . . .
C5 C 0.53363(17) 0.24464(17) 0.06899(8) 0.0196(5) Uani 1 1 d . . . . .
H5 H 0.497088 0.218859 0.093264 0.023 Uiso 1 1 calc R . . . .
C7 C 0.3919(2) 0.2697(2) 0.03080(9) 0.0307(6) Uani 1 1 d . . . . .
C1' C 0.90263(17) 0.47427(17) 0.15516(8) 0.0200(5) Uani 1 1 d . . . . .
C29 C 0.5484(2) 0.08695(18) 0.05026(8) 0.0257(5) Uani 1 1 d . . . . .
H29A H 0.488408 0.055506 0.058146 0.031 Uiso 1 1 calc R . . . .
H29B H 0.582003 0.051910 0.028364 0.031 Uiso 1 1 calc R . . . .
C4 C 0.52327(17) 0.17776(17) 0.03264(8) 0.0212(5) Uani 1 1 d . . . . .
C21 C 0.7084(2) 0.6125(2) 0.25454(9) 0.0336(7) Uani 1 1 d . . . . .
H21 H 0.650715 0.594716 0.268328 0.040 Uiso 1 1 calc R . . . .
C2' C 0.99617(18) 0.48181(19) 0.18032(8) 0.0255(6) Uani 1 1 d . . . . .
H2' H 0.978070 0.486776 0.210805 0.031 Uiso 1 1 calc R . . . .
C4' C 1.0919(2) 0.3831(2) 0.13014(9) 0.0316(6) Uani 1 1 d . . . . .
H4'A H 1.034512 0.381117 0.111511 0.038 Uiso 1 1 calc R . . . .
H4'B H 1.131107 0.434581 0.121505 0.038 Uiso 1 1 calc R . . . .
C5' C 1.1508(2) 0.3007(2) 0.12279(10) 0.0353(6) Uani 1 1 d . . . . .
H5'A H 1.170973 0.298200 0.093145 0.053 Uiso 1 1 calc GR . . . .
H5'B H 1.111486 0.248812 0.129437 0.053 Uiso 1 1 calc GR . . . .
H5'C H 1.207965 0.301596 0.141006 0.053 Uiso 1 1 calc GR . . . .
C23 C 0.8511(2) 0.6660(2) 0.24281(14) 0.0516(11) Uani 1 1 d . . . . .
H23 H 0.912681 0.692190 0.247039 0.062 Uiso 1 1 calc R . . . .
C3' C 1.05770(18) 0.3977(2) 0.17545(8) 0.0267(6) Uani 1 1 d . . . . .
H3' H 1.016653 0.346241 0.183639 0.032 Uiso 1 1 calc R . . . .
C6 C 0.47198(19) 0.32070(19) 0.05300(8) 0.0248(5) Uani 1 1 d . . . . .
H6A H 0.508110 0.358725 0.033108 0.030 Uiso 1 1 calc R . . . .
H6B H 0.446580 0.356920 0.076508 0.030 Uiso 1 1 calc R . . . .
C22 C 0.8178(2) 0.6370(2) 0.20544(12) 0.0414(8) Uani 1 1 d . . . . .
H22 H 0.850578 0.640434 0.179141 0.050 Uiso 1 1 calc R . . . .
C6' C 1.1429(2) 0.4021(3) 0.20630(11) 0.0529(11) Uani 1 1 d . . . . .
H6'A H 1.187049 0.449206 0.197599 0.079 Uiso 1 1 calc GR . . . .
H6'B H 1.177282 0.345742 0.206216 0.079 Uiso 1 1 calc GR . . . .
H6'C H 1.118796 0.414359 0.234812 0.079 Uiso 1 1 calc GR . . . .
H6 H 0.538(2) 0.484(3) 0.0969(13) 0.053(12) Uiso 1 1 d D . . . .


_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
O6 C14 1.439(3) . ?
O6 H6 0.86(2) . ?
O11 C12 1.453(3) . ?
O11 C1' 1.344(3) . ?
O5 C11 1.459(3) . ?
O5 C3 1.336(3) . ?
O3 C1 1.434(3) . ?
O3 C29 1.444(3) . ?
O9 C1' 1.206(3) . ?
O7 C15 1.209(3) . ?
O10 H10 0.8400 . ?
O10 C2' 1.409(3) . ?
O2 C7 1.345(4) . ?
O2 C4 1.477(3) . ?
O4 C3 1.210(3) . ?
O8 C21 1.354(4) . ?
O8 C23 1.384(5) . ?
O1 C7 1.203(4) . ?
C30 H30A 0.9500 . ?
C30 H30B 0.9500 . ?
C30 C8 1.336(3) . ?
C8 C14 1.497(3) . ?
C8 C9 1.537(3) . ?
C10 C19 1.530(3) . ?
C10 C9 1.581(3) . ?
C10 C1 1.572(3) . ?
C10 C5 1.547(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C13 1.533(3) . ?
C15 C14 1.541(3) . ?
C15 C16 1.521(4) . ?
C14 C13 1.551(3) . ?
C13 C12 1.528(3) . ?
C13 C17 1.567(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.534(3) . ?
C11 C9 1.562(3) . ?
C12 H12 1.0000 . ?
C9 H9 1.0000 . ?
C1 H1 1.0000 . ?
C1 C2 1.534(3) . ?
C20 C17 1.503(3) . ?
C20 C21 1.375(4) . ?
C20 C22 1.402(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.546(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.506(4) . ?
C17 H17 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C28 C4 1.524(3) . ?
C5 H5 1.0000 . ?
C5 C4 1.542(3) . ?
C5 C6 1.523(4) . ?
C7 C6 1.524(4) . ?
C1' C2' 1.525(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C4 1.528(4) . ?
C21 H21 0.9500 . ?
C2' H2' 1.0000 . ?
C2' C3' 1.543(4) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
C4' C5' 1.512(4) . ?
C4' C3' 1.527(4) . ?
C5' H5'A 0.9800 . ?
C5' H5'B 0.9800 . ?
C5' H5'C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C22 1.345(5) . ?
C3' H3' 1.0000 . ?
C3' C6' 1.533(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C22 H22 0.9500 . ?
C6' H6'A 0.9800 . ?
C6' H6'B 0.9800 . ?
C6' H6'C 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 O6 H6 109(3) . . ?
C1' O11 C12 116.48(18) . . ?
C3 O5 C11 125.06(19) . . ?
C1 O3 C29 112.89(19) . . ?
C2' O10 H10 109.5 . . ?
C7 O2 C4 108.6(2) . . ?
C21 O8 C23 104.7(2) . . ?
H30A C30 H30B 120.0 . . ?
C8 C30 H30A 120.0 . . ?
C8 C30 H30B 120.0 . . ?
C30 C8 C14 122.6(2) . . ?
C30 C8 C9 119.6(2) . . ?
C14 C8 C9 117.33(19) . . ?
C19 C10 C9 114.66(19) . . ?
C19 C10 C1 110.90(18) . . ?
C19 C10 C5 111.6(2) . . ?
C1 C10 C9 106.60(19) . . ?
C5 C10 C9 108.67(18) . . ?
C5 C10 C1 103.67(18) . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
O7 C15 C14 127.5(2) . . ?
O7 C15 C16 125.5(2) . . ?
C16 C15 C14 106.9(2) . . ?
O6 C14 C8 112.03(19) . . ?
O6 C14 C15 103.24(19) . . ?
O6 C14 C13 106.24(18) . . ?
C8 C14 C15 122.6(2) . . ?
C8 C14 C13 109.59(19) . . ?
C15 C14 C13 101.62(18) . . ?
C18 C13 C14 110.34(19) . . ?
C18 C13 C17 110.18(19) . . ?
C14 C13 C17 101.94(19) . . ?
C12 C13 C18 112.8(2) . . ?
C12 C13 C14 105.09(18) . . ?
C12 C13 C17 115.74(19) . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C11 H11 107.7 . . ?
O5 C11 C12 101.57(17) . . ?
O5 C11 C9 117.44(18) . . ?
C12 C11 H11 107.7 . . ?
C12 C11 C9 114.20(19) . . ?
C9 C11 H11 107.7 . . ?
O11 C12 C13 110.23(18) . . ?
O11 C12 C11 106.81(18) . . ?
O11 C12 H12 109.4 . . ?
C13 C12 C11 111.70(18) . . ?
C13 C12 H12 109.4 . . ?
C11 C12 H12 109.4 . . ?
C8 C9 C10 117.84(19) . . ?
C8 C9 C11 110.17(18) . . ?
C8 C9 H9 103.9 . . ?
C10 C9 H9 103.9 . . ?
C11 C9 C10 115.12(18) . . ?
C11 C9 H9 103.9 . . ?
O3 C1 C10 110.80(18) . . ?
O3 C1 H1 108.5 . . ?
O3 C1 C2 104.3(2) . . ?
C10 C1 H1 108.5 . . ?
C2 C1 C10 116.1(2) . . ?
C2 C1 H1 108.5 . . ?
C21 C20 C17 128.7(2) . . ?
C21 C20 C22 104.8(3) . . ?
C22 C20 C17 126.4(3) . . ?
C15 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
C15 C16 C17 106.8(2) . . ?
H16A C16 H16B 108.6 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 C1 111.0(2) . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C13 C17 H17 107.8 . . ?
C20 C17 C13 116.4(2) . . ?
C20 C17 C16 113.9(2) . . ?
C20 C17 H17 107.8 . . ?
C16 C17 C13 102.75(19) . . ?
C16 C17 H17 107.8 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C4 C28 H28A 109.5 . . ?
C4 C28 H28B 109.5 . . ?
C4 C28 H28C 109.5 . . ?
O5 C3 C2 119.4(2) . . ?
O4 C3 O5 117.0(2) . . ?
O4 C3 C2 123.5(2) . . ?
C10 C5 H5 105.6 . . ?
C4 C5 C10 114.24(19) . . ?
C4 C5 H5 105.6 . . ?
C6 C5 C10 122.9(2) . . ?
C6 C5 H5 105.6 . . ?
C6 C5 C4 101.5(2) . . ?
O2 C7 C6 110.8(2) . . ?
O1 C7 O2 121.2(3) . . ?
O1 C7 C6 127.9(3) . . ?
O11 C1' C2' 111.2(2) . . ?
O9 C1' O11 125.0(2) . . ?
O9 C1' C2' 123.7(2) . . ?
O3 C29 H29A 109.7 . . ?
O3 C29 H29B 109.7 . . ?
O3 C29 C4 110.0(2) . . ?
H29A C29 H29B 108.2 . . ?
C4 C29 H29A 109.7 . . ?
C4 C29 H29B 109.7 . . ?
O2 C4 C28 104.5(2) . . ?
O2 C4 C5 100.24(19) . . ?
O2 C4 C29 111.6(2) . . ?
C28 C4 C5 119.7(2) . . ?
C28 C4 C29 112.5(2) . . ?
C29 C4 C5 107.5(2) . . ?
O8 C21 C20 112.0(3) . . ?
O8 C21 H21 124.0 . . ?
C20 C21 H21 124.0 . . ?
O10 C2' C1' 109.7(2) . . ?
O10 C2' H2' 107.3 . . ?
O10 C2' C3' 114.2(2) . . ?
C1' C2' H2' 107.3 . . ?
C1' C2' C3' 110.8(2) . . ?
C3' C2' H2' 107.3 . . ?
H4'A C4' H4'B 107.4 . . ?
C5' C4' H4'A 108.4 . . ?
C5' C4' H4'B 108.4 . . ?
C5' C4' C3' 115.6(2) . . ?
C3' C4' H4'A 108.4 . . ?
C3' C4' H4'B 108.4 . . ?
C4' C5' H5'A 109.5 . . ?
C4' C5' H5'B 109.5 . . ?
C4' C5' H5'C 109.5 . . ?
H5'A C5' H5'B 109.5 . . ?
H5'A C5' H5'C 109.5 . . ?
H5'B C5' H5'C 109.5 . . ?
O8 C23 H23 124.7 . . ?
C22 C23 O8 110.6(3) . . ?
C22 C23 H23 124.7 . . ?
C2' C3' H3' 107.9 . . ?
C4' C3' C2' 112.6(2) . . ?
C4' C3' H3' 107.9 . . ?
C4' C3' C6' 111.5(2) . . ?
C6' C3' C2' 108.9(3) . . ?
C6' C3' H3' 107.9 . . ?
C5 C6 C7 100.1(2) . . ?
C5 C6 H6A 111.8 . . ?
C5 C6 H6B 111.8 . . ?
C7 C6 H6A 111.8 . . ?
C7 C6 H6B 111.8 . . ?
H6A C6 H6B 109.5 . . ?
C20 C22 H22 126.1 . . ?
C23 C22 C20 107.9(3) . . ?
C23 C22 H22 126.1 . . ?
C3' C6' H6'A 109.5 . . ?
C3' C6' H6'B 109.5 . . ?
C3' C6' H6'C 109.5 . . ?
H6'A C6' H6'B 109.5 . . ?
H6'A C6' H6'C 109.5 . . ?
H6'B C6' H6'C 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
O6 C14 C13 C18 -179.11(18) . . . . ?
O6 C14 C13 C12 -57.3(2) . . . . ?
O6 C14 C13 C17 63.9(2) . . . . ?
O11 C1' C2' O10 -150.5(2) . . . . ?
O11 C1' C2' C3' 82.5(3) . . . . ?
O5 C11 C12 O11 -57.6(2) . . . . ?
O5 C11 C12 C13 -178.16(17) . . . . ?
O5 C11 C9 C8 -158.65(19) . . . . ?
O5 C11 C9 C10 -22.5(3) . . . . ?
O3 C1 C2 C3 -176.0(2) . . . . ?
O3 C29 C4 O2 -132.9(2) . . . . ?
O3 C29 C4 C28 110.1(2) . . . . ?
O3 C29 C4 C5 -23.9(3) . . . . ?
O9 C1' C2' O10 28.7(4) . . . . ?
O9 C1' C2' C3' -98.3(3) . . . . ?
O7 C15 C14 O6 97.6(3) . . . . ?
O7 C15 C14 C8 -29.9(4) . . . . ?
O7 C15 C14 C13 -152.4(3) . . . . ?
O7 C15 C16 C17 177.3(3) . . . . ?
O10 C2' C3' C4' -60.2(3) . . . . ?
O10 C2' C3' C6' 64.0(3) . . . . ?
O2 C7 C6 C5 -16.8(3) . . . . ?
O8 C23 C22 C20 -1.6(4) . . . . ?
O1 C7 C6 C5 161.5(3) . . . . ?
C30 C8 C14 O6 -126.8(2) . . . . ?
C30 C8 C14 C15 -3.2(4) . . . . ?
C30 C8 C14 C13 115.6(3) . . . . ?
C30 C8 C9 C10 95.4(3) . . . . ?
C30 C8 C9 C11 -129.7(2) . . . . ?
C8 C14 C13 C18 -57.9(2) . . . . ?
C8 C14 C13 C12 64.0(2) . . . . ?
C8 C14 C13 C17 -174.91(19) . . . . ?
C10 C1 C2 C3 -53.8(3) . . . . ?
C10 C5 C4 O2 -177.0(2) . . . . ?
C10 C5 C4 C28 -63.7(3) . . . . ?
C10 C5 C4 C29 66.3(3) . . . . ?
C10 C5 C6 C7 165.0(2) . . . . ?
C18 C13 C12 O11 -62.7(2) . . . . ?
C18 C13 C12 C11 55.9(2) . . . . ?
C18 C13 C17 C20 48.2(3) . . . . ?
C18 C13 C17 C16 -76.9(2) . . . . ?
C15 C14 C13 C18 73.2(2) . . . . ?
C15 C14 C13 C12 -164.92(19) . . . . ?
C15 C14 C13 C17 -43.8(2) . . . . ?
C15 C16 C17 C13 -21.1(3) . . . . ?
C15 C16 C17 C20 -147.9(2) . . . . ?
C14 C8 C9 C10 -92.5(2) . . . . ?
C14 C8 C9 C11 42.3(3) . . . . ?
C14 C15 C16 C17 -6.2(3) . . . . ?
C14 C13 C12 O11 177.09(18) . . . . ?
C14 C13 C12 C11 -64.3(2) . . . . ?
C14 C13 C17 C20 165.4(2) . . . . ?
C14 C13 C17 C16 40.2(2) . . . . ?
C19 C10 C9 C8 89.1(2) . . . . ?
C19 C10 C9 C11 -43.6(3) . . . . ?
C19 C10 C1 O3 -149.3(2) . . . . ?
C19 C10 C1 C2 92.0(3) . . . . ?
C19 C10 C5 C4 83.3(3) . . . . ?
C19 C10 C5 C6 -40.2(3) . . . . ?
C11 O5 C3 O4 -174.0(2) . . . . ?
C11 O5 C3 C2 8.7(4) . . . . ?
C12 O11 C1' O9 5.2(4) . . . . ?
C12 O11 C1' C2' -175.7(2) . . . . ?
C12 C13 C17 C20 -81.2(3) . . . . ?
C12 C13 C17 C16 153.6(2) . . . . ?
C12 C11 C9 C8 -39.9(3) . . . . ?
C12 C11 C9 C10 96.3(2) . . . . ?
C9 C8 C14 O6 61.4(3) . . . . ?
C9 C8 C14 C15 -175.0(2) . . . . ?
C9 C8 C14 C13 -56.2(3) . . . . ?
C9 C10 C1 O3 85.2(2) . . . . ?
C9 C10 C1 C2 -33.5(2) . . . . ?
C9 C10 C5 C4 -149.3(2) . . . . ?
C9 C10 C5 C6 87.2(3) . . . . ?
C9 C11 C12 O11 175.02(18) . . . . ?
C9 C11 C12 C13 54.4(3) . . . . ?
C1 O3 C29 C4 -41.9(3) . . . . ?
C1 C10 C9 C8 -147.72(19) . . . . ?
C1 C10 C9 C11 79.6(2) . . . . ?
C1 C10 C5 C4 -36.2(3) . . . . ?
C1 C10 C5 C6 -159.7(2) . . . . ?
C1 C2 C3 O5 70.8(3) . . . . ?
C1 C2 C3 O4 -106.3(3) . . . . ?
C16 C15 C14 O6 -78.8(2) . . . . ?
C16 C15 C14 C8 153.8(2) . . . . ?
C16 C15 C14 C13 31.2(2) . . . . ?
C17 C13 C12 O11 65.5(3) . . . . ?
C17 C13 C12 C11 -175.92(19) . . . . ?
C17 C20 C21 O8 179.6(3) . . . . ?
C17 C20 C22 C23 -178.9(3) . . . . ?
C3 O5 C11 C12 -169.0(2) . . . . ?
C3 O5 C11 C9 -43.7(3) . . . . ?
C5 C10 C9 C8 -36.6(3) . . . . ?
C5 C10 C9 C11 -169.27(19) . . . . ?
C5 C10 C1 O3 -29.4(2) . . . . ?
C5 C10 C1 C2 -148.1(2) . . . . ?
C7 O2 C4 C28 -91.1(2) . . . . ?
C7 O2 C4 C5 33.5(3) . . . . ?
C7 O2 C4 C29 147.1(2) . . . . ?
C1' O11 C12 C13 -118.7(2) . . . . ?
C1' O11 C12 C11 119.8(2) . . . . ?
C1' C2' C3' C4' 64.3(3) . . . . ?
C1' C2' C3' C6' -171.5(3) . . . . ?
C29 O3 C1 C10 74.6(2) . . . . ?
C29 O3 C1 C2 -159.7(2) . . . . ?
C4 O2 C7 O1 170.7(3) . . . . ?
C4 O2 C7 C6 -10.8(3) . . . . ?
C4 C5 C6 C7 35.9(2) . . . . ?
C21 O8 C23 C22 1.2(4) . . . . ?
C21 C20 C17 C13 -79.5(4) . . . . ?
C21 C20 C17 C16 39.8(4) . . . . ?
C21 C20 C22 C23 1.4(4) . . . . ?
C5' C4' C3' C2' -178.7(2) . . . . ?
C5' C4' C3' C6' 58.5(4) . . . . ?
C23 O8 C21 C20 -0.3(4) . . . . ?
C6 C5 C4 O2 -42.6(2) . . . . ?
C6 C5 C4 C28 70.8(3) . . . . ?
C6 C5 C4 C29 -159.2(2) . . . . ?
C22 C20 C17 C13 100.8(3) . . . . ?
C22 C20 C17 C16 -139.9(3) . . . . ?
C22 C20 C21 O8 -0.7(4) . . . . ?

loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
1 1 2 5.147
0 2 2 6.466
1 1 3 6.024
0 0 4 5.589
1 1 5 8.232
0 2 5 9.122
0 0 6 8.401
1 1 6 9.462
0 2 6 10.249
1 1 7 10.741
2 0 8 12.967
0 2 8 12.690

_platon_squeeze_details          
;
TITL 22019688_0m_a.res in P2(1) New: C2221
CELL   13.8459   15.1850   31.6599     90.00     90.00     90.00
SPGR C2221
# Solvent Accessible Volume =      1393
# Electrons Found in S.A.V. =       245
# Note: Atoms in Void as Cxxx and Qxxx all others
Q101 0.551 0.463 0.560 !      13.12 eA-3
C102 0.219 0.500 0.500 !       8.03 eA-3
C103 0.612 0.489 0.992 !       7.60 eA-3
C104 0.768 0.030 0.961 !       5.86 eA-3
C105 0.285 0.405 0.552 !       4.65 eA-3
C106 0.306 0.471 0.512 !       4.28 eA-3
C107 0.288 0.500 0.000 !       3.42 eA-3
Q108 0.589 0.420 0.581 !       0.85 eA-3
C109 0.178 0.455 0.488 !       0.82 eA-3
C110 0.259 0.067 0.036 !       0.70 eA-3
Q111 0.593 0.459 0.024 !       0.62 eA-3
Q112 0.226 0.419 0.572 !       0.61 eA-3
Q113 0.263 0.435 0.495 !       0.60 eA-3
Q114 0.856 0.142 0.502 !       0.59 eA-3
Q115 0.796 0.301 0.360 !       0.57 eA-3
Q116 0.121 0.260 0.864 !       0.57 eA-3
Q117 0.653 0.424 0.937 !       0.57 eA-3
Q118 0.090 0.074 0.458 !       0.56 eA-3
Q119 0.219 0.438 0.021 !       0.53 eA-3
Q120 0.424 0.051 0.468 !       0.52 eA-3
Q121 0.841 0.357 0.054 !       0.52 eA-3
Q122 0.314 0.425 0.649 !       0.52 eA-3
Q123 0.832 0.472 0.978 !       0.51 eA-3
Q124 0.255 0.343 0.539 !       0.51 eA-3
Q125 0.051 0.087 0.466 !       0.51 eA-3
Q126 0.456 0.235 0.164 !       0.51 eA-3
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.074 0.000 0.000 304 61 ' '
2 0.000 0.254 0.250 42 0 ' '
3 -0.074 0.000 0.500 304 61 ' '
4 0.000 0.746 0.750 42 0 ' '
5 0.426 0.500 0.500 304 61 ' '
6 0.574 0.500 0.000 304 61 ' '
7 0.500 0.754 0.250 42 0 ' '
8 0.500 0.246 0.750 42 0 ' '

_platon_squeeze_void_probe_radius 1.20

_olex2_submission_special_instructions 'No special instructions were received'
