# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_huangxishan_285-4
_database_code_depnum_ccdc_archive 'CCDC 2020684'
loop_
_audit_author_name
_audit_author_address
'penivullactone A'
;Guangxi Normal University
China
;
_audit_update_record             
;
2020-08-01 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;
_audit_creation_date             2020-03-28
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H24 O9, O'
_chemical_formula_sum            'C25 H24 O10'
_chemical_formula_weight         484.44
_chemical_absolute_configuration ad
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.52210(10)
_cell_length_b                   12.37940(10)
_cell_length_c                   11.00760(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.4100(10)
_cell_angle_gamma                90
_cell_volume                     1108.08(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    102.0(7)
_cell_measurement_reflns_used    9368
_cell_measurement_theta_min      4.2310
_cell_measurement_theta_max      74.0130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10864
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.514
_diffrn_reflns_theta_min         4.209
_diffrn_ambient_temperature      102.0(7)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                4278
_reflns_number_total             4345
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 1952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.13(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4345
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.050
_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)+(0.0897P)²+0.5377P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1309
_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.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C24(H24A,H24B,H24C), C9(H9A,H9B,H9C),
 C20(H20A,H20B,H20C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 -0.1048(3) 0.5691(2) 0.5182(2) 0.0234(5) Uani 1 1 d . . . . .
O5 O 0.0727(3) 0.60904(19) 0.7023(2) 0.0210(5) Uani 1 1 d . . . . .
O8 O 0.0035(3) 0.5038(2) 0.9128(2) 0.0246(5) Uani 1 1 d . . . . .
O4 O 0.0181(3) 0.37362(19) 0.5082(2) 0.0214(5) Uani 1 1 d . . . . .
H4 H 0.0442 0.3144 0.5414 0.032 Uiso 1 1 calc GR . . . .
O9 O -0.0378(3) 0.3420(2) 0.8196(2) 0.0259(5) Uani 1 1 d . . . . .
O7 O 0.4899(3) 0.5914(2) 0.9096(2) 0.0244(5) Uani 1 1 d . . . . .
O2 O 0.3456(3) 0.4960(2) 0.3115(2) 0.0248(5) Uani 1 1 d . . . . .
O1 O 0.3912(3) 0.6430(2) 0.2130(2) 0.0299(6) Uani 1 1 d . . . . .
O6 O 0.3523(3) 0.7231(2) 0.7884(3) 0.0322(6) Uani 1 1 d . . . . .
C11 C 0.0224(4) 0.5462(3) 0.5982(3) 0.0189(6) Uani 1 1 d . . . . .
C1 C 0.3336(4) 0.6038(3) 0.2911(3) 0.0226(7) Uani 1 1 d . . . . .
C00C C 0.0451(4) 0.4211(3) 0.8468(3) 0.0203(6) Uani 1 1 d . . . . .
C10 C 0.1291(4) 0.4524(3) 0.5764(3) 0.0174(6) Uani 1 1 d . . . . .
C22 C 0.4137(4) 0.4395(2) 0.7041(3) 0.0187(6) Uani 1 1 d . . . . .
C3 C 0.2233(4) 0.6217(3) 0.4705(3) 0.0202(6) Uani 1 1 d . . . . .
H3 H 0.1804 0.6647 0.5222 0.024 Uiso 1 1 calc R . . . .
C17 C 0.3494(4) 0.4246(3) 0.9415(3) 0.0195(6) Uani 1 1 d . . . . .
C12 C 0.1928(4) 0.5725(3) 0.8165(3) 0.0187(6) Uani 1 1 d . . . . .
C23 C 0.2432(4) 0.4016(2) 0.7021(3) 0.0163(6) Uani 1 1 d . . . . .
C2 C 0.2601(4) 0.6671(3) 0.3732(3) 0.0227(7) Uani 1 1 d . . . . .
H2 H 0.2391 0.7402 0.3567 0.027 Uiso 1 1 calc R . . . .
C15 C 0.3526(4) 0.6343(3) 0.8343(3) 0.0227(7) Uani 1 1 d . . . . .
C16 C 0.2082(4) 0.4493(2) 0.8216(3) 0.0171(6) Uani 1 1 d . . . . .
C8 C 0.4185(4) 0.4897(3) 0.5981(3) 0.0203(6) Uani 1 1 d . . . . .
C6 C 0.2331(4) 0.4418(3) 0.3714(3) 0.0213(7) Uani 1 1 d . . . . .
C14 C 0.1184(4) 0.5937(3) 0.9257(3) 0.0233(7) Uani 1 1 d . . . . .
H14 H 0.2049 0.5876 1.0074 0.028 Uiso 1 1 calc R . . . .
C5 C 0.0610(4) 0.4481(3) 0.2737(3) 0.0258(7) Uani 1 1 d . . . . .
H5A H 0.0100 0.5153 0.2837 0.039 Uiso 1 1 calc GR . . . .
H5B H -0.0051 0.3892 0.2871 0.039 Uiso 1 1 calc GR . . . .
H5C H 0.0709 0.4439 0.1892 0.039 Uiso 1 1 calc GR . . . .
C18 C 0.3351(4) 0.3621(3) 1.0354(3) 0.0268(7) Uani 1 1 d . . . . .
C21 C 0.5527(4) 0.4232(3) 0.8236(3) 0.0222(6) Uani 1 1 d . . . . .
H21A H 0.6517 0.4565 0.8146 0.027 Uiso 1 1 calc R . . . .
H21B H 0.5736 0.3466 0.8385 0.027 Uiso 1 1 calc R . . . .
C7 C 0.2964(4) 0.3270(3) 0.3885(3) 0.0257(7) Uani 1 1 d . . . . .
H7A H 0.2972 0.2984 0.3077 0.039 Uiso 1 1 calc GR . . . .
H7B H 0.2261 0.2836 0.4225 0.039 Uiso 1 1 calc GR . . . .
H7C H 0.4060 0.3261 0.4462 0.039 Uiso 1 1 calc GR . . . .
C24 C 0.2352(4) 0.2771(3) 0.7035(3) 0.0218(7) Uani 1 1 d . . . . .
H24A H 0.1245 0.2547 0.6949 0.033 Uiso 1 1 calc GR . . . .
H24B H 0.3073 0.2505 0.7824 0.033 Uiso 1 1 calc GR . . . .
H24C H 0.2687 0.2487 0.6339 0.033 Uiso 1 1 calc GR . . . .
C4 C 0.2487(4) 0.5019(3) 0.5004(3) 0.0175(6) Uani 1 1 d . . . . .
C19 C 0.5095(4) 0.4736(3) 0.9366(3) 0.0216(7) Uani 1 1 d . . . . .
C9 C 0.5717(4) 0.5317(3) 0.5753(4) 0.0302(8) Uani 1 1 d . . . . .
H9A H 0.6565 0.5386 0.6551 0.045 Uiso 1 1 calc GR . . . .
H9B H 0.5501 0.6010 0.5347 0.045 Uiso 1 1 calc GR . . . .
H9C H 0.6069 0.4824 0.5214 0.045 Uiso 1 1 calc GR . . . .
C20 C 0.6493(4) 0.4680(3) 1.0600(3) 0.0302(8) Uani 1 1 d . . . . .
H20A H 0.7433 0.5055 1.0499 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.6776 0.3938 1.0810 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.6157 0.5010 1.1271 0.045 Uiso 1 1 calc GR . . . .
C13 C 0.0270(5) 0.6976(3) 0.9225(4) 0.0318(8) Uani 1 1 d . . . . .
H13A H -0.0622 0.7016 0.8449 0.048 Uiso 1 1 calc GR . . . .
H13B H 0.1003 0.7573 0.9266 0.048 Uiso 1 1 calc GR . . . .
H13C H -0.0156 0.7005 0.9939 0.048 Uiso 1 1 calc GR . . . .
O0AA O 0.3036(12) 0.8885(9) 0.6268(11) 0.171(4) Uani 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 C11 1.208(4) . ?
O5 C11 1.345(4) . ?
O5 C12 1.436(4) . ?
O8 C00C 1.363(4) . ?
O8 C14 1.460(4) . ?
O4 H4 0.8200 . ?
O4 C10 1.409(4) . ?
O9 C00C 1.193(4) . ?
O7 C15 1.326(4) . ?
O7 C19 1.487(4) . ?
O2 C1 1.353(4) . ?
O2 C6 1.477(4) . ?
O1 C1 1.212(4) . ?
O6 C15 1.210(5) . ?
C11 C10 1.537(4) . ?
C1 C2 1.470(5) . ?
C00C C16 1.536(4) . ?
C10 C23 1.566(4) . ?
C10 C4 1.618(4) . ?
C22 C23 1.521(4) . ?
C22 C8 1.333(5) . ?
C22 C21 1.498(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.328(5) . ?
C3 C4 1.521(4) . ?
C17 C16 1.527(4) . ?
C17 C18 1.325(5) . ?
C17 C19 1.509(4) . ?
C12 C15 1.522(4) . ?
C12 C16 1.531(4) . ?
C12 C14 1.541(4) . ?
C23 C16 1.550(4) . ?
C23 C24 1.542(4) . ?
C2 H2 0.9300 . ?
C8 C4 1.530(4) . ?
C8 C9 1.494(4) . ?
C6 C5 1.539(5) . ?
C6 C7 1.512(5) . ?
C6 C4 1.573(4) . ?
C14 H14 0.9800 . ?
C14 C13 1.499(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C19 1.533(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C19 C20 1.517(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C11 O5 C12 121.7(3) . . ?
C00C O8 C14 110.5(2) . . ?
C10 O4 H4 109.5 . . ?
C15 O7 C19 122.9(3) . . ?
C1 O2 C6 119.7(3) . . ?
O3 C11 O5 118.2(3) . . ?
O3 C11 C10 120.4(3) . . ?
O5 C11 C10 121.2(3) . . ?
O2 C1 C2 116.7(3) . . ?
O1 C1 O2 119.1(3) . . ?
O1 C1 C2 124.1(3) . . ?
O8 C00C C16 108.6(3) . . ?
O9 C00C O8 121.5(3) . . ?
O9 C00C C16 129.9(3) . . ?
O4 C10 C11 105.8(2) . . ?
O4 C10 C23 109.4(2) . . ?
O4 C10 C4 114.4(2) . . ?
C11 C10 C23 113.9(3) . . ?
C11 C10 C4 106.8(2) . . ?
C23 C10 C4 106.8(2) . . ?
C8 C22 C23 114.3(3) . . ?
C8 C22 C21 127.5(3) . . ?
C21 C22 C23 118.2(3) . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.3(3) . . ?
C4 C3 H3 118.8 . . ?
C18 C17 C16 123.9(3) . . ?
C18 C17 C19 123.9(3) . . ?
C19 C17 C16 112.1(3) . . ?
O5 C12 C15 109.3(3) . . ?
O5 C12 C16 112.1(3) . . ?
O5 C12 C14 106.1(2) . . ?
C15 C12 C16 115.6(3) . . ?
C15 C12 C14 112.1(3) . . ?
C16 C12 C14 101.0(3) . . ?
C22 C23 C10 103.0(2) . . ?
C22 C23 C16 107.2(2) . . ?
C22 C23 C24 110.7(3) . . ?
C16 C23 C10 111.7(2) . . ?
C24 C23 C10 113.1(3) . . ?
C24 C23 C16 110.6(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2 119.4 . . ?
O7 C15 C12 117.8(3) . . ?
O6 C15 O7 121.1(3) . . ?
O6 C15 C12 120.9(3) . . ?
C00C C16 C23 118.7(3) . . ?
C17 C16 C00C 108.7(2) . . ?
C17 C16 C12 105.5(3) . . ?
C17 C16 C23 110.8(2) . . ?
C12 C16 C00C 99.2(2) . . ?
C12 C16 C23 112.6(2) . . ?
C22 C8 C4 113.0(3) . . ?
C22 C8 C9 124.5(3) . . ?
C9 C8 C4 122.6(3) . . ?
O2 C6 C5 105.9(3) . . ?
O2 C6 C7 103.1(3) . . ?
O2 C6 C4 107.3(2) . . ?
C5 C6 C4 114.4(3) . . ?
C7 C6 C5 111.4(3) . . ?
C7 C6 C4 113.7(3) . . ?
O8 C14 C12 102.4(2) . . ?
O8 C14 H14 109.3 . . ?
O8 C14 C13 108.8(3) . . ?
C12 C14 H14 109.3 . . ?
C13 C14 C12 117.4(3) . . ?
C13 C14 H14 109.3 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C22 C21 H21A 109.7 . . ?
C22 C21 H21B 109.7 . . ?
C22 C21 C19 109.8(3) . . ?
H21A C21 H21B 108.2 . . ?
C19 C21 H21A 109.7 . . ?
C19 C21 H21B 109.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C3 C4 C10 114.2(3) . . ?
C3 C4 C8 106.9(3) . . ?
C3 C4 C6 107.3(2) . . ?
C8 C4 C10 102.1(2) . . ?
C8 C4 C6 113.2(3) . . ?
C6 C4 C10 113.0(2) . . ?
O7 C19 C17 110.6(3) . . ?
O7 C19 C21 106.1(3) . . ?
O7 C19 C20 103.6(3) . . ?
C17 C19 C21 107.7(3) . . ?
C17 C19 C20 115.2(3) . . ?
C20 C19 C21 113.1(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_huangxishan_285-2
_database_code_depnum_ccdc_archive 'CCDC 2020686'
loop_
_audit_author_name
_audit_author_address
'penivullactone B'
;Guangxi Normal University
China
;
_audit_update_record             
;
2020-08-01 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H26 O8'
_chemical_formula_sum            'C24 H26 O8'
_chemical_formula_weight         442.45
_chemical_absolute_configuration ad
_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                   8.33180(10)
_cell_length_b                   14.6050(2)
_cell_length_c                   17.4015(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2117.52(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    106(3)
_cell_measurement_reflns_used    7535
_cell_measurement_theta_min      5.9240
_cell_measurement_theta_max      74.1500
_shelx_estimated_absorpt_T_max   0.859
_shelx_estimated_absorpt_T_min   0.832
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_min  0.81939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10171
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.414
_diffrn_reflns_theta_min         3.952
_diffrn_ambient_temperature      106.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                4031
_reflns_number_total             4147
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1682 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.044
_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)+(0.0468P)²+0.3278P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0820
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H19 of C19, H3A of C3, H2 of C2
 At 1.5 times of:
  All C(H,H,H) groups, H8A of C8, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C12(H12A,H12B,H12C),
 C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), C8(H8A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.51339(19) 0.28749(10) 0.43086(8) 0.0287(3) Uani 1 1 d . . . . .
O2 O 0.48176(18) 0.38178(9) 0.52791(8) 0.0227(3) Uani 1 1 d . . . . .
O3 O 0.10974(16) 0.29767(9) 0.70527(8) 0.0213(3) Uani 1 1 d . . . . .
H3 H 0.0988 0.2914 0.6587 0.032 Uiso 1 1 calc GR . . . .
O4 O 0.22861(16) 0.43554(9) 0.73502(7) 0.0180(3) Uani 1 1 d . . . . .
O5 O 0.40223(19) 0.59322(10) 0.78944(9) 0.0282(3) Uani 1 1 d . . . . .
O6 O 0.51730(17) 0.49734(9) 0.86987(8) 0.0243(3) Uani 1 1 d . . . . .
O7 O -0.00329(16) 0.42950(9) 0.86826(8) 0.0243(3) Uani 1 1 d . . . . .
C8 C 0.0066(3) 0.56393(15) 0.78881(13) 0.0284(5) Uani 1 1 d . . . . .
H8A H 0.0614 0.6082 0.7765 0.043 Uiso 1 1 calc GR . . . .
C1 C 0.4697(2) 0.29771(13) 0.49674(11) 0.0221(4) Uani 1 1 d . . . . .
C2 C 0.4137(2) 0.22360(13) 0.54668(11) 0.0223(4) Uani 1 1 d . . . . .
H2 H 0.4013 0.1651 0.5264 0.027 Uiso 1 1 calc R . . . .
C3 C 0.3801(2) 0.23820(13) 0.62020(11) 0.0201(4) Uani 1 1 d . . . . .
H3A H 0.3489 0.1886 0.6502 0.024 Uiso 1 1 calc R . . . .
C4 C 0.3901(2) 0.33135(13) 0.65756(11) 0.0183(4) Uani 1 1 d . . . . .
C5 C 0.3793(2) 0.40741(13) 0.59437(11) 0.0198(4) Uani 1 1 d . . . . .
C6 C 0.2103(3) 0.41763(14) 0.56220(12) 0.0230(4) Uani 1 1 d . . . . .
H6A H 0.2119 0.4595 0.5197 0.034 Uiso 1 1 calc GR . . . .
H6B H 0.1404 0.4407 0.6015 0.034 Uiso 1 1 calc GR . . . .
H6C H 0.1721 0.3591 0.5451 0.034 Uiso 1 1 calc GR . . . .
C7 C 0.4457(3) 0.50096(13) 0.61666(12) 0.0237(4) Uani 1 1 d . . . . .
H7A H 0.5432 0.4932 0.6454 0.036 Uiso 1 1 calc GR . . . .
H7B H 0.3684 0.5328 0.6476 0.036 Uiso 1 1 calc GR . . . .
H7C H 0.4676 0.5358 0.5710 0.036 Uiso 1 1 calc GR . . . .
C0AA C 0.5417(2) 0.33568(13) 0.70805(12) 0.0208(4) Uani 1 1 d . . . . .
C9 C 0.7072(3) 0.33889(16) 0.67434(13) 0.0283(5) Uani 1 1 d . . . . .
H9A H 0.7313 0.2812 0.6506 0.043 Uiso 1 1 calc GR . . . .
H9B H 0.7838 0.3509 0.7143 0.043 Uiso 1 1 calc GR . . . .
H9C H 0.7125 0.3867 0.6365 0.043 Uiso 1 1 calc GR . . . .
C10 C 0.5052(2) 0.32677(12) 0.78254(11) 0.0196(4) Uani 1 1 d . . . . .
C11 C 0.3302(2) 0.30377(12) 0.79558(11) 0.0179(4) Uani 1 1 d . . . . .
C12 C 0.3061(3) 0.20210(13) 0.81435(12) 0.0230(4) Uani 1 1 d . . . . .
H12A H 0.3677 0.1655 0.7792 0.034 Uiso 1 1 calc GR . . . .
H12B H 0.1945 0.1868 0.8096 0.034 Uiso 1 1 calc GR . . . .
H12C H 0.3411 0.1903 0.8660 0.034 Uiso 1 1 calc GR . . . .
C13 C 0.2567(2) 0.33930(12) 0.72042(11) 0.0180(4) Uani 1 1 d . . . . .
C14 C 0.2579(2) 0.36825(13) 0.85708(11) 0.0182(4) Uani 1 1 d . . . . .
C15 C 0.2500(2) 0.45863(12) 0.81405(11) 0.0171(4) Uani 1 1 d . . . . .
C16 C 0.3964(2) 0.52092(13) 0.82253(11) 0.0202(4) Uani 1 1 d . . . . .
C17 C 0.0819(2) 0.35146(13) 0.87653(11) 0.0208(4) Uani 1 1 d . . . . .
O18 O 0.01946(19) 0.28205(10) 0.89879(9) 0.0291(3) Uani 1 1 d . . . . .
C19 C 0.0982(2) 0.50564(13) 0.84480(11) 0.0210(4) Uani 1 1 d . . . . .
H19 H 0.1260 0.5424 0.8900 0.025 Uiso 1 1 calc R . . . .
C20 C 0.6102(2) 0.33980(15) 0.85134(12) 0.0241(4) Uani 1 1 d . . . . .
H20A H 0.7134 0.3640 0.8355 0.029 Uiso 1 1 calc R . . . .
H20B H 0.6281 0.2813 0.8763 0.029 Uiso 1 1 calc R . . . .
C21 C 0.5298(3) 0.40668(14) 0.90820(11) 0.0229(4) Uani 1 1 d . . . . .
C22 C 0.6368(3) 0.42454(16) 0.97705(13) 0.0304(5) Uani 1 1 d . . . . .
H22A H 0.7357 0.4516 0.9601 0.046 Uiso 1 1 calc GR . . . .
H22B H 0.6590 0.3678 1.0028 0.046 Uiso 1 1 calc GR . . . .
H22C H 0.5835 0.4655 1.0118 0.046 Uiso 1 1 calc GR . . . .
C23 C 0.3626(2) 0.37311(13) 0.92764(11) 0.0201(4) Uani 1 1 d . . . . .
C24 C 0.3172(3) 0.34701(14) 0.99721(12) 0.0259(4) Uani 1 1 d . . . . .
H24A H 0.209(4) 0.3280(18) 1.0055(16) 0.037(7) Uiso 1 1 d . . . . .
H24B H 0.382(3) 0.3500(17) 1.0406(15) 0.027(6) Uiso 1 1 d . . . . .
H8B H -0.024(3) 0.5286(19) 0.7396(16) 0.035(7) Uiso 1 1 d . . . . .
H8C H -0.094(3) 0.5868(18) 0.8145(16) 0.035(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
O1 C1 1.212(2) . ?
O2 C1 1.346(2) . ?
O2 C5 1.485(2) . ?
O3 H3 0.8200 . ?
O3 C13 1.392(2) . ?
O4 C13 1.447(2) . ?
O4 C15 1.427(2) . ?
O5 C16 1.204(2) . ?
O6 C16 1.346(2) . ?
O6 C21 1.486(2) . ?
O7 C17 1.350(2) . ?
O7 C19 1.456(2) . ?
C8 H8A 0.8200 . ?
C8 C19 1.502(3) . ?
C8 H8B 1.03(3) . ?
C8 H8C 1.01(3) . ?
C1 C2 1.465(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.327(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.510(2) . ?
C4 C5 1.566(3) . ?
C4 C0AA 1.540(3) . ?
C4 C13 1.564(3) . ?
C5 C6 1.523(3) . ?
C5 C7 1.524(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C0AA C9 1.499(3) . ?
C0AA C10 1.338(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.514(3) . ?
C10 C20 1.495(3) . ?
C11 C12 1.533(3) . ?
C11 C13 1.535(3) . ?
C11 C14 1.547(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.519(2) . ?
C14 C17 1.524(3) . ?
C14 C23 1.508(3) . ?
C15 C16 1.529(3) . ?
C15 C19 1.535(3) . ?
C17 O18 1.204(2) . ?
C19 H19 0.9800 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.543(3) . ?
C21 C22 1.516(3) . ?
C21 C23 1.515(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.324(3) . ?
C24 H24A 0.96(3) . ?
C24 H24B 0.93(3) . ?

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 O2 C5 120.06(15) . . ?
C13 O3 H3 109.5 . . ?
C15 O4 C13 112.25(13) . . ?
C16 O6 C21 123.69(15) . . ?
C17 O7 C19 111.66(15) . . ?
H8A C8 H8B 108.3 . . ?
H8A C8 H8C 108.6 . . ?
C19 C8 H8A 109.5 . . ?
C19 C8 H8B 112.2(16) . . ?
C19 C8 H8C 108.8(16) . . ?
H8B C8 H8C 109(2) . . ?
O1 C1 O2 118.11(18) . . ?
O1 C1 C2 124.47(19) . . ?
O2 C1 C2 117.31(17) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.36(18) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3A 118.4 . . ?
C2 C3 C4 123.26(17) . . ?
C4 C3 H3A 118.4 . . ?
C3 C4 C5 109.49(15) . . ?
C3 C4 C0AA 109.12(15) . . ?
C3 C4 C13 109.21(15) . . ?
C0AA C4 C5 114.73(16) . . ?
C0AA C4 C13 100.43(14) . . ?
C13 C4 C5 113.46(15) . . ?
O2 C5 C4 109.59(14) . . ?
O2 C5 C6 105.66(15) . . ?
O2 C5 C7 102.44(15) . . ?
C6 C5 C4 112.37(16) . . ?
C6 C5 C7 109.96(16) . . ?
C7 C5 C4 115.88(16) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C0AA C4 122.18(17) . . ?
C10 C0AA C4 111.25(18) . . ?
C10 C0AA C9 126.23(19) . . ?
C0AA C9 H9A 109.5 . . ?
C0AA C9 H9B 109.5 . . ?
C0AA C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C0AA C10 C11 112.69(17) . . ?
C0AA C10 C20 129.12(18) . . ?
C20 C10 C11 118.14(16) . . ?
C10 C11 C12 111.88(15) . . ?
C10 C11 C13 100.46(15) . . ?
C10 C11 C14 110.10(15) . . ?
C12 C11 C13 117.18(16) . . ?
C12 C11 C14 113.03(16) . . ?
C13 C11 C14 103.20(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O4 108.38(15) . . ?
O3 C13 C4 117.40(15) . . ?
O3 C13 C11 111.39(15) . . ?
O4 C13 C4 108.04(14) . . ?
O4 C13 C11 104.07(14) . . ?
C11 C13 C4 106.71(15) . . ?
C15 C14 C11 101.82(14) . . ?
C15 C14 C17 101.98(15) . . ?
C17 C14 C11 115.47(16) . . ?
C23 C14 C11 111.51(15) . . ?
C23 C14 C15 112.67(16) . . ?
C23 C14 C17 112.52(16) . . ?
O4 C15 C14 105.96(14) . . ?
O4 C15 C16 109.46(15) . . ?
O4 C15 C19 109.81(15) . . ?
C14 C15 C16 115.78(16) . . ?
C14 C15 C19 104.63(15) . . ?
C16 C15 C19 110.94(14) . . ?
O5 C16 O6 119.12(18) . . ?
O5 C16 C15 120.55(18) . . ?
O6 C16 C15 120.26(16) . . ?
O7 C17 C14 110.26(16) . . ?
O18 C17 O7 121.19(18) . . ?
O18 C17 C14 128.52(18) . . ?
O7 C19 C8 108.63(16) . . ?
O7 C19 C15 103.57(14) . . ?
O7 C19 H19 109.3 . . ?
C8 C19 C15 116.48(17) . . ?
C8 C19 H19 109.3 . . ?
C15 C19 H19 109.3 . . ?
C10 C20 H20A 109.7 . . ?
C10 C20 H20B 109.7 . . ?
C10 C20 C21 109.89(16) . . ?
H20A C20 H20B 108.2 . . ?
C21 C20 H20A 109.7 . . ?
C21 C20 H20B 109.7 . . ?
O6 C21 C20 107.84(16) . . ?
O6 C21 C22 104.03(16) . . ?
O6 C21 C23 108.93(15) . . ?
C22 C21 C20 111.10(17) . . ?
C23 C21 C20 109.72(17) . . ?
C23 C21 C22 114.84(17) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C23 C21 111.42(16) . . ?
C24 C23 C14 124.4(2) . . ?
C24 C23 C21 124.05(19) . . ?
C23 C24 H24A 119.4(17) . . ?
C23 C24 H24B 124.3(16) . . ?
H24A C24 H24B 116(2) . . ?

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
O1 C1 C2 C3 174.4(2) . . . . ?
O2 C1 C2 C3 -1.7(3) . . . . ?
O4 C15 C16 O5 59.0(2) . . . . ?
O4 C15 C16 O6 -123.93(18) . . . . ?
O4 C15 C19 O7 86.09(17) . . . . ?
O4 C15 C19 C8 -33.1(2) . . . . ?
O6 C21 C23 C14 56.8(2) . . . . ?
O6 C21 C23 C24 -126.4(2) . . . . ?
C1 O2 C5 C4 49.7(2) . . . . ?
C1 O2 C5 C6 -71.6(2) . . . . ?
C1 O2 C5 C7 173.23(16) . . . . ?
C1 C2 C3 C4 2.5(3) . . . . ?
C2 C3 C4 C5 21.4(3) . . . . ?
C2 C3 C4 C0AA -105.0(2) . . . . ?
C2 C3 C4 C13 146.14(19) . . . . ?
C3 C4 C5 O2 -43.7(2) . . . . ?
C3 C4 C5 C6 73.5(2) . . . . ?
C3 C4 C5 C7 -158.92(17) . . . . ?
C3 C4 C0AA C9 70.7(2) . . . . ?
C3 C4 C0AA C10 -103.02(18) . . . . ?
C3 C4 C13 O3 -36.4(2) . . . . ?
C3 C4 C13 O4 -159.26(14) . . . . ?
C3 C4 C13 C11 89.35(17) . . . . ?
C4 C0AA C10 C11 6.9(2) . . . . ?
C4 C0AA C10 C20 -170.57(18) . . . . ?
C5 O2 C1 O1 157.25(18) . . . . ?
C5 O2 C1 C2 -26.4(2) . . . . ?
C5 C4 C0AA C9 -52.6(2) . . . . ?
C5 C4 C0AA C10 133.72(17) . . . . ?
C5 C4 C13 O3 86.0(2) . . . . ?
C5 C4 C13 O4 -36.8(2) . . . . ?
C5 C4 C13 C11 -148.22(15) . . . . ?
C0AA C4 C5 O2 79.41(19) . . . . ?
C0AA C4 C5 C6 -163.44(16) . . . . ?
C0AA C4 C5 C7 -35.8(2) . . . . ?
C0AA C4 C13 O3 -151.06(16) . . . . ?
C0AA C4 C13 O4 86.10(16) . . . . ?
C0AA C4 C13 C11 -25.29(18) . . . . ?
C0AA C10 C11 C12 102.58(19) . . . . ?
C0AA C10 C11 C13 -22.5(2) . . . . ?
C0AA C10 C11 C14 -130.85(17) . . . . ?
C0AA C10 C20 C21 127.4(2) . . . . ?
C9 C0AA C10 C11 -166.55(19) . . . . ?
C9 C0AA C10 C20 16.0(3) . . . . ?
C10 C11 C13 O3 158.10(15) . . . . ?
C10 C11 C13 O4 -85.33(16) . . . . ?
C10 C11 C13 C4 28.79(17) . . . . ?
C10 C11 C14 C15 71.26(18) . . . . ?
C10 C11 C14 C17 -179.20(15) . . . . ?
C10 C11 C14 C23 -49.1(2) . . . . ?
C10 C20 C21 O6 -64.1(2) . . . . ?
C10 C20 C21 C22 -177.49(17) . . . . ?
C10 C20 C21 C23 54.4(2) . . . . ?
C11 C10 C20 C21 -49.9(2) . . . . ?
C11 C14 C15 O4 29.63(19) . . . . ?
C11 C14 C15 C16 -91.89(18) . . . . ?
C11 C14 C15 C19 145.67(15) . . . . ?
C11 C14 C17 O7 -125.82(17) . . . . ?
C11 C14 C17 O18 56.5(3) . . . . ?
C11 C14 C23 C21 58.8(2) . . . . ?
C11 C14 C23 C24 -118.0(2) . . . . ?
C12 C11 C13 O3 36.7(2) . . . . ?
C12 C11 C13 O4 153.29(15) . . . . ?
C12 C11 C13 C4 -92.60(19) . . . . ?
C12 C11 C14 C15 -162.82(16) . . . . ?
C12 C11 C14 C17 -53.3(2) . . . . ?
C12 C11 C14 C23 76.8(2) . . . . ?
C13 O4 C15 C14 -12.6(2) . . . . ?
C13 O4 C15 C16 112.92(16) . . . . ?
C13 O4 C15 C19 -125.06(15) . . . . ?
C13 C4 C5 O2 -165.93(14) . . . . ?
C13 C4 C5 C6 -48.8(2) . . . . ?
C13 C4 C5 C7 78.8(2) . . . . ?
C13 C4 C0AA C9 -174.60(18) . . . . ?
C13 C4 C0AA C10 11.7(2) . . . . ?
C13 C11 C14 C15 -35.27(18) . . . . ?
C13 C11 C14 C17 74.27(19) . . . . ?
C13 C11 C14 C23 -155.66(16) . . . . ?
C14 C11 C13 O3 -88.18(18) . . . . ?
C14 C11 C13 O4 28.40(18) . . . . ?
C14 C11 C13 C4 142.51(15) . . . . ?
C14 C15 C16 O5 178.67(18) . . . . ?
C14 C15 C16 O6 -4.3(2) . . . . ?
C14 C15 C19 O7 -27.24(18) . . . . ?
C14 C15 C19 C8 -146.41(17) . . . . ?
C15 O4 C13 O3 108.32(17) . . . . ?
C15 O4 C13 C4 -123.50(16) . . . . ?
C15 O4 C13 C11 -10.3(2) . . . . ?
C15 C14 C17 O7 -16.4(2) . . . . ?
C15 C14 C17 O18 166.0(2) . . . . ?
C15 C14 C23 C21 -55.0(2) . . . . ?
C15 C14 C23 C24 128.2(2) . . . . ?
C16 O6 C21 C20 84.5(2) . . . . ?
C16 O6 C21 C22 -157.41(17) . . . . ?
C16 O6 C21 C23 -34.5(2) . . . . ?
C16 C15 C19 O7 -152.78(15) . . . . ?
C16 C15 C19 C8 88.0(2) . . . . ?
C17 O7 C19 C8 142.27(16) . . . . ?
C17 O7 C19 C15 17.8(2) . . . . ?
C17 C14 C15 O4 -89.94(17) . . . . ?
C17 C14 C15 C16 148.53(16) . . . . ?
C17 C14 C15 C19 26.10(18) . . . . ?
C17 C14 C23 C21 -169.66(16) . . . . ?
C17 C14 C23 C24 13.5(3) . . . . ?
C19 O7 C17 C14 -1.0(2) . . . . ?
C19 O7 C17 O18 176.86(18) . . . . ?
C19 C15 C16 O5 -62.3(2) . . . . ?
C19 C15 C16 O6 114.73(18) . . . . ?
C20 C10 C11 C12 -79.7(2) . . . . ?
C20 C10 C11 C13 155.25(17) . . . . ?
C20 C10 C11 C14 46.9(2) . . . . ?
C20 C21 C23 C14 -61.1(2) . . . . ?
C20 C21 C23 C24 115.7(2) . . . . ?
C21 O6 C16 O5 -174.43(17) . . . . ?
C21 O6 C16 C15 8.5(3) . . . . ?
C22 C21 C23 C14 172.96(17) . . . . ?
C22 C21 C23 C24 -10.2(3) . . . . ?
C23 C14 C15 O4 149.19(16) . . . . ?
C23 C14 C15 C16 27.7(2) . . . . ?
C23 C14 C15 C19 -94.77(18) . . . . ?
C23 C14 C17 O7 104.61(18) . . . . ?
C23 C14 C17 O18 -73.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_huangxishan_285-3
_database_code_depnum_ccdc_archive 'CCDC 2020689'
loop_
_audit_author_name
_audit_author_address
hydroxyisoaustinone
;Guangxi Normal University
China
;
_audit_update_record             
;
2020-08-01 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;
_audit_creation_date             2020-07-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H30 O7, C H4 O'
_chemical_formula_sum            'C26 H34 O8'
_chemical_formula_weight         474.53
_chemical_absolute_configuration ad
_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                   8.70681(4)
_cell_length_b                   12.24332(6)
_cell_length_c                   21.97785(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2342.844(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(3)
_cell_measurement_reflns_used    23886
_cell_measurement_theta_min      5.4030
_cell_measurement_theta_max      73.9950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.818
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29855
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.404
_diffrn_reflns_theta_min         4.023
_diffrn_ambient_temperature      110(3)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                4668
_reflns_number_total             4734
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1983 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.05(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4734
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0405P)²+0.5685P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0774
_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.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00Q(H00Q)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00B), C00P(H00I,H00J)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00H(H00H)
2.d Idealised Me refined as rotating group:
 C00O(H00D,H00F,H00G), C00R(H00K,H00L,H00M), C00T(H00N,H00O,H00P), C00U(H00R,
 H00S,H00T), C00V(H00U,H00V,H00W), C00W(H00X,H00Y,H), C00Y(H00,HA,HB)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3), O8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O4 O 0.27172(15) 0.80002(10) 0.60182(5) 0.0224(3) Uani 1 1 d . . . . .
H4 H 0.3565 0.8284 0.6054 0.034 Uiso 1 1 calc R U . . .
O2 O 0.57139(15) 0.37946(11) 0.55506(6) 0.0253(3) Uani 1 1 d . . . . .
O6 O -0.03804(16) 0.90237(11) 0.63239(6) 0.0276(3) Uani 1 1 d . . . . .
O5 O 0.42173(16) 0.80622(12) 0.72020(6) 0.0311(3) Uani 1 1 d . . . . .
O3 O 0.08322(16) 0.40575(11) 0.56174(7) 0.0289(3) Uani 1 1 d . . . . .
H3 H -0.0055 0.4111 0.5495 0.043 Uiso 1 1 calc R U . . .
O8 O 0.54835(16) 0.88595(12) 0.58786(7) 0.0312(3) Uani 1 1 d . . . . .
H8 H 0.6190 0.8420 0.5910 0.047 Uiso 1 1 calc R U . . .
O1 O 0.78599(15) 0.44969(13) 0.51947(7) 0.0322(3) Uani 1 1 d . . . . .
O7 O -0.19168(17) 0.76259(12) 0.60915(7) 0.0341(3) Uani 1 1 d . . . . .
C009 C 0.6500(2) 0.46222(16) 0.53048(8) 0.0246(4) Uani 1 1 d . . . . .
C00A C 0.3386(2) 0.51939(14) 0.64032(8) 0.0217(4) Uani 1 1 d . . . . .
C00B C 0.2227(2) 0.56903(14) 0.66987(8) 0.0216(4) Uani 1 1 d . . . . .
C00C C 0.4267(2) 0.58104(15) 0.54062(8) 0.0230(4) Uani 1 1 d . . . . .
H00C H 0.3822 0.6493 0.5348 0.028 Uiso 1 1 calc R U . . .
C00D C -0.0734(2) 0.79524(15) 0.63121(8) 0.0248(4) Uani 1 1 d . . . . .
C00E C 0.1659(2) 0.50302(15) 0.54691(8) 0.0225(4) Uani 1 1 d . . . . .
H00E H 0.1714 0.5084 0.5025 0.027 Uiso 1 1 calc R U . . .
C00F C 0.0742(2) 0.60891(14) 0.64037(8) 0.0215(3) Uani 1 1 d . . . . .
C00G C 0.4002(2) 0.37896(15) 0.55271(9) 0.0231(4) Uani 1 1 d . . . . .
C00H C 0.5700(2) 0.56584(16) 0.52128(8) 0.0255(4) Uani 1 1 d . . . . .
H00H H 0.6204 0.6225 0.5014 0.031 Uiso 1 1 calc R U . . .
C00I C 0.0313(2) 0.73333(15) 0.73136(8) 0.0248(4) Uani 1 1 d . . . . .
C00J C 0.1927(2) 0.80802(15) 0.65673(8) 0.0217(4) Uani 1 1 d . . . . .
C00K C 0.1906(2) 0.71189(16) 0.75586(8) 0.0253(4) Uani 1 1 d . . . . .
C00L C 0.2884(2) 0.78107(15) 0.71308(8) 0.0237(4) Uani 1 1 d . . . . .
C00M C 0.3322(2) 0.49327(14) 0.57157(8) 0.0209(3) Uani 1 1 d . . . . .
C00N C 0.2331(2) 0.59186(15) 0.73794(8) 0.0251(4) Uani 1 1 d . . . . .
H00A H 0.3370 0.5768 0.7515 0.030 Uiso 1 1 calc R U . . .
H00B H 0.1649 0.5422 0.7592 0.030 Uiso 1 1 calc R U . . .
C00O C 0.3628(2) 0.34844(16) 0.48709(9) 0.0268(4) Uani 1 1 d . . . . .
H00D H 0.3856 0.4091 0.4609 0.040 Uiso 1 1 calc R U . . .
H00F H 0.2557 0.3305 0.4839 0.040 Uiso 1 1 calc R U . . .
H00G H 0.4234 0.2865 0.4752 0.040 Uiso 1 1 calc R U . . .
C00P C 0.0834(2) 0.60413(14) 0.57056(8) 0.0225(3) Uani 1 1 d . . . . .
H00I H -0.0199 0.6055 0.5541 0.027 Uiso 1 1 calc R U . . .
H00J H 0.1365 0.6686 0.5559 0.027 Uiso 1 1 calc R U . . .
C00Q C 0.1089(2) 0.91959(15) 0.66345(9) 0.0254(4) Uani 1 1 d . . . . .
H00Q H 0.0894 0.9335 0.7067 0.031 Uiso 1 1 calc R U . . .
C00R C 0.4892(2) 0.49642(18) 0.67293(9) 0.0300(4) Uani 1 1 d . . . . .
H00K H 0.5312 0.5636 0.6881 0.045 Uiso 1 1 calc R U . . .
H00L H 0.5605 0.4637 0.6450 0.045 Uiso 1 1 calc R U . . .
H00M H 0.4711 0.4474 0.7062 0.045 Uiso 1 1 calc R U . . .
C00S C 0.0523(2) 0.73017(15) 0.66204(8) 0.0226(4) Uani 1 1 d . . . . .
C00T C 0.3592(2) 0.28568(16) 0.59536(10) 0.0292(4) Uani 1 1 d . . . . .
H00N H 0.4098 0.2202 0.5821 0.044 Uiso 1 1 calc R U . . .
H00O H 0.2501 0.2746 0.5950 0.044 Uiso 1 1 calc R U . . .
H00P H 0.3918 0.3034 0.6359 0.044 Uiso 1 1 calc R U . . .
C00U C 0.1875(3) 1.01694(16) 0.63645(10) 0.0303(4) Uani 1 1 d . . . . .
H00R H 0.2191 1.0004 0.5956 0.046 Uiso 1 1 calc R U . . .
H00S H 0.2759 1.0351 0.6605 0.046 Uiso 1 1 calc R U . . .
H00T H 0.1179 1.0777 0.6359 0.046 Uiso 1 1 calc R U . . .
C00V C -0.0629(2) 0.54004(16) 0.66295(9) 0.0286(4) Uani 1 1 d . . . . .
H00U H -0.0467 0.4648 0.6524 0.043 Uiso 1 1 calc R U . . .
H00V H -0.1556 0.5657 0.6441 0.043 Uiso 1 1 calc R U . . .
H00W H -0.0716 0.5468 0.7063 0.043 Uiso 1 1 calc R U . . .
C00W C 0.2182(3) 0.73225(17) 0.82301(9) 0.0321(4) Uani 1 1 d . . . . .
H00X H 0.1872 0.8053 0.8331 0.048 Uiso 1 1 calc R U . . .
H00Y H 0.3254 0.7233 0.8319 0.048 Uiso 1 1 calc R U . . .
H H 0.1595 0.6811 0.8466 0.048 Uiso 1 1 calc R U . . .
C00X C -0.0954(3) 0.75620(18) 0.76191(10) 0.0338(5) Uani 1 1 d . . . . .
C00Y C 0.5875(3) 0.98350(19) 0.61855(11) 0.0376(5) Uani 1 1 d . . . . .
H00 H 0.5321 1.0435 0.6009 0.056 Uiso 1 1 calc R U . . .
HA H 0.6958 0.9963 0.6147 0.056 Uiso 1 1 calc R U . . .
HB H 0.5610 0.9769 0.6608 0.056 Uiso 1 1 calc R U . . .
H00Z H -0.191(3) 0.768(2) 0.7403(12) 0.043(7) Uiso 1 1 d . . . . .
HC H -0.090(3) 0.763(2) 0.8060(13) 0.045(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
O4 H4 0.8200 . ?
O4 C00J 1.392(2) . ?
O2 C009 1.337(2) . ?
O2 C00G 1.492(2) . ?
O6 C00D 1.348(2) . ?
O6 C00Q 1.465(2) . ?
O5 C00L 1.211(2) . ?
O3 H3 0.8200 . ?
O3 C00E 1.429(2) . ?
O8 H8 0.8200 . ?
O8 C00Y 1.413(3) . ?
O1 C009 1.218(2) . ?
O7 C00D 1.206(2) . ?
C009 C00H 1.461(3) . ?
C00A C00B 1.345(3) . ?
C00A C00M 1.546(2) . ?
C00A C00R 1.521(3) . ?
C00B C00F 1.526(2) . ?
C00B C00N 1.525(2) . ?
C00C H00C 0.9300 . ?
C00C C00H 1.331(3) . ?
C00C C00M 1.515(2) . ?
C00D C00S 1.513(3) . ?
C00E H00E 0.9800 . ?
C00E C00M 1.551(2) . ?
C00E C00P 1.523(2) . ?
C00F C00P 1.538(2) . ?
C00F C00S 1.571(2) . ?
C00F C00V 1.543(3) . ?
C00G C00M 1.575(2) . ?
C00G C00O 1.525(3) . ?
C00G C00T 1.520(3) . ?
C00H H00H 0.9300 . ?
C00I C00K 1.511(3) . ?
C00I C00S 1.535(2) . ?
C00I C00X 1.321(3) . ?
C00J C00L 1.529(3) . ?
C00J C00Q 1.556(2) . ?
C00J C00S 1.555(3) . ?
C00K C00L 1.525(3) . ?
C00K C00N 1.566(3) . ?
C00K C00W 1.516(3) . ?
C00N H00A 0.9700 . ?
C00N H00B 0.9700 . ?
C00O H00D 0.9600 . ?
C00O H00F 0.9600 . ?
C00O H00G 0.9600 . ?
C00P H00I 0.9700 . ?
C00P H00J 0.9700 . ?
C00Q H00Q 0.9800 . ?
C00Q C00U 1.497(3) . ?
C00R H00K 0.9600 . ?
C00R H00L 0.9600 . ?
C00R H00M 0.9600 . ?
C00T H00N 0.9600 . ?
C00T H00O 0.9600 . ?
C00T H00P 0.9600 . ?
C00U H00R 0.9600 . ?
C00U H00S 0.9600 . ?
C00U H00T 0.9600 . ?
C00V H00U 0.9600 . ?
C00V H00V 0.9600 . ?
C00V H00W 0.9600 . ?
C00W H00X 0.9600 . ?
C00W H00Y 0.9600 . ?
C00W H 0.9600 . ?
C00X H00Z 0.97(3) . ?
C00X HC 0.97(3) . ?
C00Y H00 0.9600 . ?
C00Y HA 0.9600 . ?
C00Y HB 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
C00J O4 H4 109.5 . . ?
C009 O2 C00G 120.06(14) . . ?
C00D O6 C00Q 110.39(14) . . ?
C00E O3 H3 109.5 . . ?
C00Y O8 H8 109.5 . . ?
O2 C009 C00H 118.03(16) . . ?
O1 C009 O2 118.85(18) . . ?
O1 C009 C00H 123.03(19) . . ?
C00B C00A C00M 122.59(16) . . ?
C00B C00A C00R 120.19(16) . . ?
C00R C00A C00M 116.96(15) . . ?
C00A C00B C00F 125.08(16) . . ?
C00A C00B C00N 120.81(16) . . ?
C00N C00B C00F 114.10(15) . . ?
C00H C00C H00C 118.2 . . ?
C00H C00C C00M 123.59(17) . . ?
C00M C00C H00C 118.2 . . ?
O6 C00D C00S 109.79(16) . . ?
O7 C00D O6 121.68(18) . . ?
O7 C00D C00S 128.51(18) . . ?
O3 C00E H00E 107.9 . . ?
O3 C00E C00M 109.06(14) . . ?
O3 C00E C00P 111.21(15) . . ?
C00M C00E H00E 107.9 . . ?
C00P C00E H00E 107.9 . . ?
C00P C00E C00M 112.58(14) . . ?
C00B C00F C00P 111.58(15) . . ?
C00B C00F C00S 106.06(14) . . ?
C00B C00F C00V 110.10(15) . . ?
C00P C00F C00S 110.17(14) . . ?
C00P C00F C00V 109.89(15) . . ?
C00V C00F C00S 108.94(15) . . ?
O2 C00G C00M 111.27(14) . . ?
O2 C00G C00O 104.31(14) . . ?
O2 C00G C00T 102.50(15) . . ?
C00O C00G C00M 112.72(15) . . ?
C00T C00G C00M 114.66(15) . . ?
C00T C00G C00O 110.42(16) . . ?
C009 C00H H00H 119.2 . . ?
C00C C00H C009 121.59(18) . . ?
C00C C00H H00H 119.2 . . ?
C00K C00I C00S 103.91(15) . . ?
C00X C00I C00K 128.45(18) . . ?
C00X C00I C00S 127.52(19) . . ?
O4 C00J C00L 114.68(15) . . ?
O4 C00J C00Q 112.08(15) . . ?
O4 C00J C00S 114.24(14) . . ?
C00L C00J C00Q 111.61(15) . . ?
C00L C00J C00S 103.61(14) . . ?
C00S C00J C00Q 99.34(14) . . ?
C00I C00K C00L 101.32(15) . . ?
C00I C00K C00N 106.88(16) . . ?
C00I C00K C00W 117.66(16) . . ?
C00L C00K C00N 103.54(14) . . ?
C00W C00K C00L 114.86(17) . . ?
C00W C00K C00N 111.20(16) . . ?
O5 C00L C00J 124.90(17) . . ?
O5 C00L C00K 126.62(17) . . ?
C00K C00L C00J 108.37(15) . . ?
C00A C00M C00E 111.06(14) . . ?
C00A C00M C00G 115.32(14) . . ?
C00C C00M C00A 105.82(14) . . ?
C00C C00M C00E 107.19(14) . . ?
C00C C00M C00G 107.95(14) . . ?
C00E C00M C00G 109.11(14) . . ?
C00B C00N C00K 113.88(15) . . ?
C00B C00N H00A 108.8 . . ?
C00B C00N H00B 108.8 . . ?
C00K C00N H00A 108.8 . . ?
C00K C00N H00B 108.8 . . ?
H00A C00N H00B 107.7 . . ?
C00G C00O H00D 109.5 . . ?
C00G C00O H00F 109.5 . . ?
C00G C00O H00G 109.5 . . ?
H00D C00O H00F 109.5 . . ?
H00D C00O H00G 109.5 . . ?
H00F C00O H00G 109.5 . . ?
C00E C00P C00F 113.33(14) . . ?
C00E C00P H00I 108.9 . . ?
C00E C00P H00J 108.9 . . ?
C00F C00P H00I 108.9 . . ?
C00F C00P H00J 108.9 . . ?
H00I C00P H00J 107.7 . . ?
O6 C00Q C00J 103.83(14) . . ?
O6 C00Q H00Q 109.0 . . ?
O6 C00Q C00U 109.21(15) . . ?
C00J C00Q H00Q 109.0 . . ?
C00U C00Q C00J 116.55(16) . . ?
C00U C00Q H00Q 109.0 . . ?
C00A C00R H00K 109.5 . . ?
C00A C00R H00L 109.5 . . ?
C00A C00R H00M 109.5 . . ?
H00K C00R H00L 109.5 . . ?
H00K C00R H00M 109.5 . . ?
H00L C00R H00M 109.5 . . ?
C00D C00S C00F 116.73(15) . . ?
C00D C00S C00I 110.20(15) . . ?
C00D C00S C00J 102.25(14) . . ?
C00I C00S C00F 109.83(14) . . ?
C00I C00S C00J 98.78(14) . . ?
C00J C00S C00F 117.44(15) . . ?
C00G C00T H00N 109.5 . . ?
C00G C00T H00O 109.5 . . ?
C00G C00T H00P 109.5 . . ?
H00N C00T H00O 109.5 . . ?
H00N C00T H00P 109.5 . . ?
H00O C00T H00P 109.5 . . ?
C00Q C00U H00R 109.5 . . ?
C00Q C00U H00S 109.5 . . ?
C00Q C00U H00T 109.5 . . ?
H00R C00U H00S 109.5 . . ?
H00R C00U H00T 109.5 . . ?
H00S C00U H00T 109.5 . . ?
C00F C00V H00U 109.5 . . ?
C00F C00V H00V 109.5 . . ?
C00F C00V H00W 109.5 . . ?
H00U C00V H00V 109.5 . . ?
H00U C00V H00W 109.5 . . ?
H00V C00V H00W 109.5 . . ?
C00K C00W H00X 109.5 . . ?
C00K C00W H00Y 109.5 . . ?
C00K C00W H 109.5 . . ?
H00X C00W H00Y 109.5 . . ?
H00X C00W H 109.5 . . ?
H00Y C00W H 109.5 . . ?
C00I C00X H00Z 119.9(16) . . ?
C00I C00X HC 119.1(17) . . ?
H00Z C00X HC 121(2) . . ?
O8 C00Y H00 109.5 . . ?
O8 C00Y HA 109.5 . . ?
O8 C00Y HB 109.5 . . ?
H00 C00Y HA 109.5 . . ?
H00 C00Y HB 109.5 . . ?
HA C00Y HB 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
O4 C00J C00L O5 38.6(3) . . . . ?
O4 C00J C00L C00K -137.85(16) . . . . ?
O4 C00J C00Q O6 85.39(17) . . . . ?
O4 C00J C00Q C00U -34.7(2) . . . . ?
O4 C00J C00S C00D -84.79(17) . . . . ?
O4 C00J C00S C00F 44.4(2) . . . . ?
O4 C00J C00S C00I 162.19(15) . . . . ?
O2 C009 C00H C00C 4.9(3) . . . . ?
O2 C00G C00M C00A -74.46(19) . . . . ?
O2 C00G C00M C00C 43.60(19) . . . . ?
O2 C00G C00M C00E 159.77(14) . . . . ?
O6 C00D C00S C00F -152.53(15) . . . . ?
O6 C00D C00S C00I 81.32(19) . . . . ?
O6 C00D C00S C00J -22.94(19) . . . . ?
O3 C00E C00M C00A -80.23(17) . . . . ?
O3 C00E C00M C00C 164.63(14) . . . . ?
O3 C00E C00M C00G 47.97(18) . . . . ?
O3 C00E C00P C00F 64.75(19) . . . . ?
O1 C009 C00H C00C -171.60(18) . . . . ?
O7 C00D C00S C00F 29.1(3) . . . . ?
O7 C00D C00S C00I -97.1(2) . . . . ?
O7 C00D C00S C00J 158.64(19) . . . . ?
C009 O2 C00G C00M -46.4(2) . . . . ?
C009 O2 C00G C00O 75.44(19) . . . . ?
C009 O2 C00G C00T -169.39(16) . . . . ?
C00A C00B C00F C00P -10.0(2) . . . . ?
C00A C00B C00F C00S -130.03(18) . . . . ?
C00A C00B C00F C00V 112.3(2) . . . . ?
C00A C00B C00N C00K 131.03(19) . . . . ?
C00B C00A C00M C00C 101.2(2) . . . . ?
C00B C00A C00M C00E -14.8(2) . . . . ?
C00B C00A C00M C00G -139.61(18) . . . . ?
C00B C00F C00P C00E 39.3(2) . . . . ?
C00B C00F C00S C00D 170.40(15) . . . . ?
C00B C00F C00S C00I -63.26(18) . . . . ?
C00B C00F C00S C00J 48.46(19) . . . . ?
C00D O6 C00Q C00J 23.83(18) . . . . ?
C00D O6 C00Q C00U 148.80(16) . . . . ?
C00F C00B C00N C00K -48.0(2) . . . . ?
C00G O2 C009 O1 -162.32(16) . . . . ?
C00G O2 C009 C00H 21.1(2) . . . . ?
C00H C00C C00M C00A 101.27(19) . . . . ?
C00H C00C C00M C00E -140.14(18) . . . . ?
C00H C00C C00M C00G -22.7(2) . . . . ?
C00I C00K C00L O5 166.35(19) . . . . ?
C00I C00K C00L C00J -17.31(18) . . . . ?
C00I C00K C00N C00B 56.0(2) . . . . ?
C00K C00I C00S C00D -155.90(15) . . . . ?
C00K C00I C00S C00F 74.14(18) . . . . ?
C00K C00I C00S C00J -49.32(16) . . . . ?
C00L C00J C00Q O6 -144.41(15) . . . . ?
C00L C00J C00Q C00U 95.47(19) . . . . ?
C00L C00J C00S C00D 149.74(14) . . . . ?
C00L C00J C00S C00F -81.11(18) . . . . ?
C00L C00J C00S C00I 36.73(17) . . . . ?
C00L C00K C00N C00B -50.5(2) . . . . ?
C00M C00A C00B C00F -1.9(3) . . . . ?
C00M C00A C00B C00N 179.18(16) . . . . ?
C00M C00C C00H C009 -2.1(3) . . . . ?
C00M C00E C00P C00F -58.0(2) . . . . ?
C00N C00B C00F C00P 168.90(15) . . . . ?
C00N C00B C00F C00S 48.91(19) . . . . ?
C00N C00B C00F C00V -68.81(19) . . . . ?
C00N C00K C00L O5 -83.0(2) . . . . ?
C00N C00K C00L C00J 93.35(17) . . . . ?
C00O C00G C00M C00A 168.76(15) . . . . ?
C00O C00G C00M C00C -73.18(18) . . . . ?
C00O C00G C00M C00E 42.99(19) . . . . ?
C00P C00E C00M C00A 43.7(2) . . . . ?
C00P C00E C00M C00C -71.44(18) . . . . ?
C00P C00E C00M C00G 171.90(15) . . . . ?
C00P C00F C00S C00D 49.5(2) . . . . ?
C00P C00F C00S C00I 175.84(15) . . . . ?
C00P C00F C00S C00J -72.45(19) . . . . ?
C00Q O6 C00D O7 178.07(18) . . . . ?
C00Q O6 C00D C00S -0.5(2) . . . . ?
C00Q C00J C00L O5 -90.3(2) . . . . ?
C00Q C00J C00L C00K 93.32(17) . . . . ?
C00Q C00J C00S C00D 34.66(17) . . . . ?
C00Q C00J C00S C00F 163.81(15) . . . . ?
C00Q C00J C00S C00I -78.35(15) . . . . ?
C00R C00A C00B C00F 172.13(17) . . . . ?
C00R C00A C00B C00N -6.7(3) . . . . ?
C00R C00A C00M C00C -73.10(19) . . . . ?
C00R C00A C00M C00E 170.90(16) . . . . ?
C00R C00A C00M C00G 46.1(2) . . . . ?
C00S C00F C00P C00E 156.88(15) . . . . ?
C00S C00I C00K C00L 41.63(17) . . . . ?
C00S C00I C00K C00N -66.45(17) . . . . ?
C00S C00I C00K C00W 167.70(17) . . . . ?
C00S C00J C00L O5 163.75(17) . . . . ?
C00S C00J C00L C00K -12.67(18) . . . . ?
C00S C00J C00Q O6 -35.65(16) . . . . ?
C00S C00J C00Q C00U -155.76(16) . . . . ?
C00T C00G C00M C00A 41.3(2) . . . . ?
C00T C00G C00M C00C 159.33(16) . . . . ?
C00T C00G C00M C00E -84.50(19) . . . . ?
C00V C00F C00P C00E -83.08(19) . . . . ?
C00V C00F C00S C00D -71.11(19) . . . . ?
C00V C00F C00S C00I 55.2(2) . . . . ?
C00V C00F C00S C00J 166.94(15) . . . . ?
C00W C00K C00L O5 38.4(3) . . . . ?
C00W C00K C00L C00J -145.22(17) . . . . ?
C00W C00K C00N C00B -174.41(16) . . . . ?
C00X C00I C00K C00L -134.6(2) . . . . ?
C00X C00I C00K C00N 117.3(2) . . . . ?
C00X C00I C00K C00W -8.6(3) . . . . ?
C00X C00I C00S C00D 20.4(3) . . . . ?
C00X C00I C00S C00F -109.5(2) . . . . ?
C00X C00I C00S C00J 127.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2036643'
loop_
_audit_author_name
_audit_author_address
compound
;Guangxi Normal University
China
;
_audit_update_record             
;
2020-10-12 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;
_audit_creation_date             2020-07-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.5(C25 H28 O7), 0.5(C H4 O)'
_chemical_formula_sum            'C13 H16 O4'
_chemical_formula_weight         236.26
_chemical_absolute_configuration ad
_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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'

_cell_length_a                   8.30120(10)
_cell_length_b                   8.44520(10)
_cell_length_c                   9.7416(2)
_cell_angle_alpha                88.4430(10)
_cell_angle_beta                 68.237(2)
_cell_angle_gamma                69.518(2)
_cell_volume                     590.022(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    102.3(9)
_cell_measurement_reflns_used    10133
_cell_measurement_theta_min      4.9360
_cell_measurement_theta_max      73.9700
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11370
_diffrn_reflns_theta_full        74.14
_diffrn_reflns_theta_max         74.14
_diffrn_reflns_theta_min         4.92
_diffrn_ambient_temperature      102.3(9)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4456
_reflns_number_total             4466
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4466
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0460P)²+0.0647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0711
_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. 
;
_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.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C31(H31)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C34(H34A,H34B,H34C), C32(H32A,H32B,H32C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.89886(13) 0.88724(12) 0.94003(10) 0.02193(19) Uani 1 1 d . . .
O3 O 1.37035(13) 0.13050(11) 0.21797(10) 0.02025(18) Uani 1 1 d . . .
O4 O 1.43655(12) 0.40159(12) 0.55236(11) 0.0236(2) Uani 1 1 d . . .
O5 O 1.05297(12) 0.51530(11) 0.80302(10) 0.01917(18) Uani 1 1 d . . .
H5 H 1.0407 0.4325 0.8454 0.029 Uiso 1 1 calc R . .
O6 O 1.40518(14) -0.13917(12) 0.23412(11) 0.0281(2) Uani 1 1 d . . .
O7 O 0.99515(13) 1.00958(11) 0.73627(10) 0.0225(2) Uani 1 1 d . . .
O8 O 0.69786(14) 0.46081(12) 0.89240(12) 0.0277(2) Uani 1 1 d . . .
C9 C 0.93316(17) 0.90483(16) 0.79549(14) 0.0182(2) Uani 1 1 d . . .
C10 C 0.92489(17) 0.56663(15) 0.53877(13) 0.0157(2) Uani 1 1 d . . .
C11 C 0.66987(17) 0.85966(16) 0.76141(13) 0.0172(2) Uani 1 1 d . . .
C12 C 1.30504(17) 0.45762(16) 0.51534(13) 0.0178(2) Uani 1 1 d . . .
C13 C 0.99131(17) 0.70748(14) 0.56244(13) 0.0159(2) Uani 1 1 d . . .
C14 C 1.37277(18) 0.28983(16) 0.27569(14) 0.0184(2) Uani 1 1 d . . .
C15 C 0.81489(18) 0.75765(16) 0.98705(14) 0.0206(3) Uani 1 1 d . . .
H15 H 0.6788 0.8128 1.0288 0.025 Uiso 1 1 calc R . .
C16 C 0.72261(17) 0.58563(16) 0.84042(14) 0.0187(2) Uani 1 1 d . . .
C17 C 0.95668(18) 0.27803(16) 0.45519(14) 0.0190(2) Uani 1 1 d . . .
H17A H 0.9177 0.2258 0.5442 0.028 Uiso 1 1 calc R . .
H17B H 1.0503 0.1921 0.3755 0.028 Uiso 1 1 calc R . .
H17C H 0.8516 0.3355 0.4292 0.028 Uiso 1 1 calc R . .
C18 C 1.24739(17) 0.33414(15) 0.44745(13) 0.0161(2) Uani 1 1 d . . .
C19 C 1.03619(16) 0.40521(15) 0.48153(13) 0.0153(2) Uani 1 1 d . . .
C20 C 0.87825(16) 0.78055(15) 0.73077(13) 0.0158(2) Uani 1 1 d . . .
C21 C 0.94556(19) 0.84736(16) 0.46273(14) 0.0201(3) Uani 1 1 d . . .
H21A H 1.0091 0.7995 0.3602 0.030 Uiso 1 1 calc R . .
H21B H 0.9855 0.9366 0.4787 0.030 Uiso 1 1 calc R . .
H21C H 0.8136 0.8930 0.4873 0.030 Uiso 1 1 calc R . .
C22 C 1.2975(2) 0.41933(17) 0.18253(15) 0.0236(3) Uani 1 1 d . . .
H22A H 1.3740 0.3822 0.0790 0.035 Uiso 1 1 calc R . .
H22B H 1.2990 0.5274 0.2088 0.035 Uiso 1 1 calc R . .
H22C H 1.1720 0.4304 0.2008 0.035 Uiso 1 1 calc R . .
C23 C 1.20385(17) 0.64444(16) 0.52332(14) 0.0184(2) Uani 1 1 d . . .
H23A H 1.2609 0.6804 0.4278 0.022 Uiso 1 1 calc R . .
H23B H 1.2240 0.7021 0.5967 0.022 Uiso 1 1 calc R . .
C24 C 1.36278(18) 0.01908(16) 0.44934(15) 0.0212(3) Uani 1 1 d . . .
H24 H 1.3974 -0.0753 0.4982 0.025 Uiso 1 1 calc R . .
C25 C 1.38491(17) -0.00597(17) 0.29448(14) 0.0210(3) Uani 1 1 d . . .
C26 C 0.71341(17) 0.62236(16) 0.59338(14) 0.0183(2) Uani 1 1 d . . .
H26A H 0.6812 0.5240 0.5856 0.022 Uiso 1 1 calc R . .
H26B H 0.6693 0.7024 0.5302 0.022 Uiso 1 1 calc R . .
C27 C 0.40712(18) 0.73918(17) 0.82232(15) 0.0236(3) Uani 1 1 d . . .
H27A H 0.3540 0.7839 0.9254 0.035 Uiso 1 1 calc R . .
H27B H 0.3896 0.6340 0.8132 0.035 Uiso 1 1 calc R . .
H27C H 0.3469 0.8196 0.7686 0.035 Uiso 1 1 calc R . .
C28 C 1.57820(17) 0.25936(18) 0.23847(15) 0.0243(3) Uani 1 1 d . . .
H28A H 1.6230 0.1804 0.3007 0.036 Uiso 1 1 calc R . .
H28B H 1.5906 0.3652 0.2555 0.036 Uiso 1 1 calc R . .
H28C H 1.6498 0.2134 0.1359 0.036 Uiso 1 1 calc R . .
C29 C 0.87781(17) 0.64516(15) 0.84035(13) 0.0169(2) Uani 1 1 d . . .
C30 C 0.61394(17) 0.70767(16) 0.75861(14) 0.0182(2) Uani 1 1 d . . .
C31 C 1.29410(16) 0.17426(16) 0.52161(13) 0.0184(2) Uani 1 1 d . . .
H31 H 1.2740 0.1849 0.6220 0.022 Uiso 1 1 calc R . .
C33 C 0.56471(19) 1.02324(17) 0.78568(15) 0.0220(3) Uani 1 1 d . . .
C34 C 0.8784(2) 0.6690(2) 1.10397(16) 0.0304(3) Uani 1 1 d . . .
H34A H 1.0120 0.6168 1.0636 0.046 Uiso 1 1 calc R . .
H34B H 0.8255 0.5831 1.1349 0.046 Uiso 1 1 calc R . .
H34C H 0.8384 0.7503 1.1880 0.046 Uiso 1 1 calc R . .
O2 O 0.08817(13) 0.20621(12) 0.89988(10) 0.02216(19) Uani 1 1 d . . .
H2 H 0.0455 0.1525 0.8634 0.033 Uiso 1 1 calc R . .
C32 C 0.0637(2) 0.16616(19) 1.04779(15) 0.0248(3) Uani 1 1 d . . .
H32A H 0.0401 0.0622 1.0609 0.037 Uiso 1 1 calc R . .
H32B H -0.0401 0.2567 1.1176 0.037 Uiso 1 1 calc R . .
H32C H 0.1745 0.1527 1.0644 0.037 Uiso 1 1 calc R . .
H33A H 0.430(2) 1.0644(19) 0.8043(17) 0.013(3) Uiso 1 1 d . . .
H33B H 0.620(3) 1.110(2) 0.782(2) 0.028(4) 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
O1 C9 1.3441(15) . ?
O1 C15 1.4708(15) . ?
O3 C14 1.4817(15) . ?
O3 C25 1.3495(16) . ?
O4 C12 1.2111(15) . ?
O5 H5 0.8200 . ?
O5 C29 1.4010(15) . ?
O6 C25 1.2123(16) . ?
O7 C9 1.2045(16) . ?
O8 C16 1.2063(16) . ?
C9 C20 1.5136(16) . ?
C10 C13 1.5297(15) . ?
C10 C19 1.3419(17) . ?
C10 C26 1.5262(16) . ?
C11 C20 1.5319(16) . ?
C11 C30 1.5140(17) . ?
C11 C33 1.3218(19) . ?
C12 C18 1.5412(16) . ?
C12 C23 1.4938(18) . ?
C13 C20 1.5681(16) . ?
C13 C21 1.5429(16) . ?
C13 C23 1.5481(16) . ?
C14 C18 1.5790(16) . ?
C14 C22 1.5159(17) . ?
C14 C28 1.5314(17) . ?
C15 H15 0.9800 . ?
C15 C29 1.5462(17) . ?
C15 C34 1.5032(18) . ?
C16 C29 1.5379(16) . ?
C16 C30 1.5327(17) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 C19 1.5139(16) . ?
C18 C19 1.5451(16) . ?
C18 C31 1.5111(17) . ?
C20 C29 1.5429(16) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24 0.9300 . ?
C24 C25 1.4625(18) . ?
C24 C31 1.3296(19) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C30 1.5661(17) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C27 C30 1.5174(17) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C31 H31 0.9300 . ?
C33 H33A 0.995(16) . ?
C33 H33B 0.987(18) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
O2 H2 0.8200 . ?
O2 C32 1.4270(16) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 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
C9 O1 C15 110.59(9) . . ?
C25 O3 C14 121.34(9) . . ?
C29 O5 H5 109.5 . . ?
O1 C9 C20 109.61(10) . . ?
O7 C9 O1 121.23(11) . . ?
O7 C9 C20 129.14(11) . . ?
C19 C10 C13 125.11(11) . . ?
C19 C10 C26 120.91(10) . . ?
C26 C10 C13 113.92(10) . . ?
C30 C11 C20 104.00(10) . . ?
C33 C11 C20 127.42(11) . . ?
C33 C11 C30 128.57(12) . . ?
O4 C12 C18 119.52(11) . . ?
O4 C12 C23 122.06(11) . . ?
C23 C12 C18 118.28(10) . . ?
C10 C13 C20 105.35(9) . . ?
C10 C13 C21 109.47(9) . . ?
C10 C13 C23 113.40(10) . . ?
C21 C13 C20 110.16(9) . . ?
C21 C13 C23 107.26(10) . . ?
C23 C13 C20 111.21(9) . . ?
O3 C14 C18 109.95(9) . . ?
O3 C14 C22 103.10(10) . . ?
O3 C14 C28 105.88(10) . . ?
C22 C14 C18 113.02(10) . . ?
C22 C14 C28 110.23(11) . . ?
C28 C14 C18 113.87(10) . . ?
O1 C15 H15 109.5 . . ?
O1 C15 C29 103.77(9) . . ?
O1 C15 C34 108.64(11) . . ?
C29 C15 H15 109.5 . . ?
C34 C15 H15 109.5 . . ?
C34 C15 C29 115.82(11) . . ?
O8 C16 C29 124.75(11) . . ?
O8 C16 C30 127.19(11) . . ?
C30 C16 C29 108.01(10) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C17 H17A 109.5 . . ?
C19 C17 H17B 109.5 . . ?
C19 C17 H17C 109.5 . . ?
C12 C18 C14 108.63(9) . . ?
C12 C18 C19 111.78(10) . . ?
C19 C18 C14 113.47(9) . . ?
C31 C18 C12 105.18(10) . . ?
C31 C18 C14 108.33(10) . . ?
C31 C18 C19 109.07(9) . . ?
C10 C19 C17 120.78(10) . . ?
C10 C19 C18 123.29(10) . . ?
C17 C19 C18 115.83(10) . . ?
C9 C20 C11 109.18(10) . . ?
C9 C20 C13 118.23(10) . . ?
C9 C20 C29 102.91(10) . . ?
C11 C20 C13 109.74(9) . . ?
C11 C20 C29 100.30(9) . . ?
C29 C20 C13 114.84(10) . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C23 C13 117.53(10) . . ?
C12 C23 H23A 107.9 . . ?
C12 C23 H23B 107.9 . . ?
C13 C23 H23A 107.9 . . ?
C13 C23 H23B 107.9 . . ?
H23A C23 H23B 107.2 . . ?
C25 C24 H24 119.4 . . ?
C31 C24 H24 119.4 . . ?
C31 C24 C25 121.24(11) . . ?
O3 C25 C24 117.63(11) . . ?
O6 C25 O3 118.43(12) . . ?
O6 C25 C24 123.81(12) . . ?
C10 C26 H26A 109.3 . . ?
C10 C26 H26B 109.3 . . ?
C10 C26 C30 111.78(9) . . ?
H26A C26 H26B 107.9 . . ?
C30 C26 H26A 109.3 . . ?
C30 C26 H26B 109.3 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C30 C27 H27A 109.5 . . ?
C30 C27 H27B 109.5 . . ?
C30 C27 H27C 109.5 . . ?
C14 C28 H28A 109.5 . . ?
C14 C28 H28B 109.5 . . ?
C14 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O5 C29 C15 113.06(9) . . ?
O5 C29 C16 114.82(10) . . ?
O5 C29 C20 112.74(10) . . ?
C16 C29 C15 110.75(10) . . ?
C16 C29 C20 103.94(9) . . ?
C20 C29 C15 100.23(9) . . ?
C11 C30 C16 101.72(9) . . ?
C11 C30 C26 106.09(10) . . ?
C11 C30 C27 117.34(11) . . ?
C16 C30 C26 104.11(10) . . ?
C27 C30 C16 113.75(11) . . ?
C27 C30 C26 112.46(10) . . ?
C18 C31 H31 118.6 . . ?
C24 C31 C18 122.73(11) . . ?
C24 C31 H31 118.6 . . ?
C11 C33 H33A 122.5(9) . . ?
C11 C33 H33B 120.2(11) . . ?
H33A C33 H33B 117.3(13) . . ?
C15 C34 H34A 109.5 . . ?
C15 C34 H34B 109.5 . . ?
C15 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 O2 H2 109.5 . . ?
O2 C32 H32A 109.5 . . ?
O2 C32 H32B 109.5 . . ?
O2 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
O1 C9 C20 C11 85.18(12) . . . . ?
O1 C9 C20 C13 -148.47(10) . . . . ?
O1 C9 C20 C29 -20.72(13) . . . . ?
O1 C15 C29 O5 86.16(11) . . . . ?
O1 C15 C29 C16 -143.36(10) . . . . ?
O1 C15 C29 C20 -34.08(11) . . . . ?
O3 C14 C18 C12 160.15(9) . . . . ?
O3 C14 C18 C19 -74.87(12) . . . . ?
O3 C14 C18 C31 46.39(12) . . . . ?
O4 C12 C18 C14 -83.61(13) . . . . ?
O4 C12 C18 C19 150.42(11) . . . . ?
O4 C12 C18 C31 32.19(15) . . . . ?
O4 C12 C23 C13 -145.87(12) . . . . ?
O7 C9 C20 C11 -93.40(15) . . . . ?
O7 C9 C20 C13 32.95(19) . . . . ?
O7 C9 C20 C29 160.70(13) . . . . ?
O8 C16 C29 O5 43.37(17) . . . . ?
O8 C16 C29 C15 -86.17(15) . . . . ?
O8 C16 C29 C20 166.99(12) . . . . ?
O8 C16 C30 C11 164.38(13) . . . . ?
O8 C16 C30 C26 -85.50(15) . . . . ?
O8 C16 C30 C27 37.25(18) . . . . ?
C9 O1 C15 C29 23.46(12) . . . . ?
C9 O1 C15 C34 147.23(11) . . . . ?
C9 C20 C29 O5 -87.78(12) . . . . ?
C9 C20 C29 C15 32.70(11) . . . . ?
C9 C20 C29 C16 147.26(10) . . . . ?
C10 C13 C20 C9 170.87(10) . . . . ?
C10 C13 C20 C11 -63.05(11) . . . . ?
C10 C13 C20 C29 49.00(12) . . . . ?
C10 C13 C23 C12 -18.64(15) . . . . ?
C10 C26 C30 C11 59.27(12) . . . . ?
C10 C26 C30 C16 -47.61(12) . . . . ?
C10 C26 C30 C27 -171.20(10) . . . . ?
C11 C20 C29 O5 159.63(9) . . . . ?
C11 C20 C29 C15 -79.90(10) . . . . ?
C11 C20 C29 C16 34.66(11) . . . . ?
C12 C18 C19 C10 11.47(15) . . . . ?
C12 C18 C19 C17 -164.93(10) . . . . ?
C12 C18 C31 C24 -141.91(12) . . . . ?
C13 C10 C19 C17 -176.69(11) . . . . ?
C13 C10 C19 C18 7.09(17) . . . . ?
C13 C10 C26 C30 -52.30(13) . . . . ?
C13 C20 C29 O5 42.08(13) . . . . ?
C13 C20 C29 C15 162.55(9) . . . . ?
C13 C20 C29 C16 -82.88(11) . . . . ?
C14 O3 C25 O6 -171.06(11) . . . . ?
C14 O3 C25 C24 12.91(16) . . . . ?
C14 C18 C19 C10 -111.80(12) . . . . ?
C14 C18 C19 C17 71.80(13) . . . . ?
C14 C18 C31 C24 -25.89(16) . . . . ?
C15 O1 C9 O7 177.01(12) . . . . ?
C15 O1 C9 C20 -1.70(13) . . . . ?
C18 C12 C23 C13 38.46(16) . . . . ?
C19 C10 C13 C20 -125.73(12) . . . . ?
C19 C10 C13 C21 115.84(13) . . . . ?
C19 C10 C13 C23 -3.89(16) . . . . ?
C19 C10 C26 C30 125.14(12) . . . . ?
C19 C18 C31 C24 98.05(13) . . . . ?
C20 C11 C30 C16 40.47(12) . . . . ?
C20 C11 C30 C26 -68.13(11) . . . . ?
C20 C11 C30 C27 165.24(10) . . . . ?
C20 C13 C23 C12 99.87(12) . . . . ?
C21 C13 C20 C9 -71.17(13) . . . . ?
C21 C13 C20 C11 54.91(12) . . . . ?
C21 C13 C20 C29 166.97(10) . . . . ?
C21 C13 C23 C12 -139.62(11) . . . . ?
C22 C14 C18 C12 -85.26(12) . . . . ?
C22 C14 C18 C19 39.72(14) . . . . ?
C22 C14 C18 C31 160.99(10) . . . . ?
C23 C12 C18 C14 92.17(13) . . . . ?
C23 C12 C18 C19 -33.80(14) . . . . ?
C23 C12 C18 C31 -152.03(10) . . . . ?
C23 C13 C20 C9 47.62(14) . . . . ?
C23 C13 C20 C11 173.70(9) . . . . ?
C23 C13 C20 C29 -74.25(12) . . . . ?
C25 O3 C14 C18 -43.23(14) . . . . ?
C25 O3 C14 C22 -164.00(11) . . . . ?
C25 O3 C14 C28 80.20(13) . . . . ?
C25 C24 C31 C18 -4.48(19) . . . . ?
C26 C10 C13 C20 51.58(12) . . . . ?
C26 C10 C13 C21 -66.85(13) . . . . ?
C26 C10 C13 C23 173.42(10) . . . . ?
C26 C10 C19 C17 6.17(17) . . . . ?
C26 C10 C19 C18 -170.05(10) . . . . ?
C28 C14 C18 C12 41.53(14) . . . . ?
C28 C14 C18 C19 166.51(10) . . . . ?
C28 C14 C18 C31 -72.22(13) . . . . ?
C29 C16 C30 C11 -17.89(12) . . . . ?
C29 C16 C30 C26 92.23(11) . . . . ?
C29 C16 C30 C27 -145.02(11) . . . . ?
C30 C11 C20 C9 -155.12(10) . . . . ?
C30 C11 C20 C13 73.82(11) . . . . ?
C30 C11 C20 C29 -47.44(11) . . . . ?
C30 C16 C29 O5 -134.43(10) . . . . ?
C30 C16 C29 C15 96.03(11) . . . . ?
C30 C16 C29 C20 -10.81(12) . . . . ?
C31 C18 C19 C10 127.35(12) . . . . ?
C31 C18 C19 C17 -49.05(13) . . . . ?
C31 C24 C25 O3 13.37(18) . . . . ?
C31 C24 C25 O6 -162.43(13) . . . . ?
C33 C11 C20 C9 24.40(17) . . . . ?
C33 C11 C20 C13 -106.67(14) . . . . ?
C33 C11 C20 C29 132.08(13) . . . . ?
C33 C11 C30 C16 -139.04(13) . . . . ?
C33 C11 C30 C26 112.36(14) . . . . ?
C33 C11 C30 C27 -14.3(2) . . . . ?
C34 C15 C29 O5 -32.79(15) . . . . ?
C34 C15 C29 C16 97.69(13) . . . . ?
C34 C15 C29 C20 -153.03(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_huangxishan_285-13
_database_code_depnum_ccdc_archive 'CCDC 2020687'
loop_
_audit_author_name
_audit_author_address
'penivullactone C'
;Guangxi Normal University
China
;
_audit_update_record             
;
2020-08-01 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C25 H26 O8'
_chemical_formula_sum            'C25 H26 O8'
_chemical_formula_weight         454.48
_chemical_absolute_configuration ad
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           ' C 2y'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z
3 x+1/2,y+1/2,z
4 -x+1/2,y+1/2,-z

_symmetry_Int_Tables_number      5
_cell_length_a                   20.3188(2)
_cell_length_b                   8.20450(10)
_cell_length_c                   13.22130(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.3740(10)
_cell_angle_gamma                90
_cell_volume                     2203.43(4)
_cell_formula_units_Z            4
_exptl_absorpt_coefficient_mu    0.853
_exptl_crystal_density_diffrn    1.3699
_exptl_crystal_F_000             963.4950
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_description       block
_cell_measurement_temperature    101.8(6)
_cell_measurement_reflns_used    9643
_cell_measurement_theta_min      4.3360
_cell_measurement_theta_max      73.8620
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11749
_diffrn_reflns_theta_full        74.1586
_diffrn_reflns_theta_max         74.16
_diffrn_reflns_theta_min         4.35
_diffrn_ambient_temperature      101.8(6)
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.8494
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.699
_reflns_limit_h_max              25
_reflns_limit_h_min              -24
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              16
_reflns_limit_l_min              -16
_reflns_number_gt                3754
_reflns_number_total             3823
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.3677
_refine_diff_density_min         -0.1713
_refine_diff_density_rms         0.0416
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.08(8)
_refine_ls_d_res_high            0.8014
_refine_ls_d_res_low             10.1565
_refine_ls_goodness_of_fit_ref   0.8226
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    6
_refine_ls_number_parameters     388
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      0.8226
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0886
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
2.b Idealised tetrahedral OH refined as rotating group:
 O0aa(H0aa)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O0aa O 0.32166(5) 0.50681(12) 0.57969(7) 0.0221(2) Uani 1.000000 .
H0aa H 0.3124(10) 0.6034(7) 0.5723(4) 0.0331(3) Uiso 1.000000 GR
O O 0.21897(4) 0.52559(12) 0.79614(7) 0.0209(2) Uani 1.000000 .
O2aa O 0.11373(5) 0.41624(13) 0.64520(7) 0.0248(2) Uani 1.000000 .
O3aa O 0.17161(5) 0.32052(12) 0.51656(7) 0.0248(2) Uani 1.000000 .
O4aa O 0.19464(5) 0.29870(13) 0.96207(7) 0.0262(2) Uani 1.000000 .
O5aa O 0.53786(6) 0.6605(2) 0.89765(8) 0.0443(4) Uani 1.000000 .
O6aa O 0.49293(5) 0.50393(17) 0.77963(7) 0.0318(3) Uani 1.000000 .
O1aa O 0.25705(5) 0.71821(13) 0.69564(8) 0.0253(2) Uani 1.000000 .
C1aa C 0.19717(6) 0.25613(17) 0.87507(10) 0.0210(3) Uani 1.000000 .
C2aa C 0.30976(6) 0.45991(16) 0.67968(9) 0.0191(3) Uani 1.000000 .
C3aa C 0.16573(6) 0.33656(16) 0.60578(10) 0.0197(3) Uani 1.000000 .
C4aa C 0.25851(6) 0.57781(17) 0.72132(9) 0.0201(3) Uani 1.000000 .
C5aa C 0.37333(6) 0.46954(17) 0.75565(9) 0.0211(3) Uani 1.000000 .
C6aa C 0.48812(7) 0.6175(2) 0.85257(10) 0.0319(4) Uani 1.000000 .
C7aa C 0.36884(7) 0.60546(18) 0.83386(10) 0.0235(3) Uani 1.000000 .
C8aa C 0.18716(6) 0.37029(16) 0.78323(9) 0.0195(3) Uani 1.000000 .
C C 0.21105(7) 0.08509(17) 0.83364(10) 0.0220(3) Uani 1.000000 .
C0ba C 0.31685(6) 0.21728(18) 0.78099(9) 0.0208(3) Uani 1.000000 .
C1ba C 0.36737(6) 0.30932(18) 0.81424(10) 0.0217(3) Uani 1.000000 .
C2ba C 0.28550(6) 0.27943(17) 0.68268(9) 0.0189(3) Uani 1.000000 .
C1 C 0.18141(7) -0.05075(18) 0.89474(11) 0.0266(3) Uani 1.000000 .
H1a H 0.1947(5) -0.0390(9) 0.96452(19) 0.0398(4) Uiso 1.000000 GR
H1b H 0.13428(7) -0.0457(9) 0.8887(8) 0.0398(4) Uiso 1.000000 GR
H1c H 0.1964(5) -0.15388(19) 0.8698(6) 0.0398(4) Uiso 1.000000 GR
C4ba C 0.20951(6) 0.27274(16) 0.69265(9) 0.0190(3) Uani 1.000000 .
C5ba C 0.18793(6) 0.10228(17) 0.72424(9) 0.0202(3) Uani 1.000000 .
C6ba C 0.42170(7) 0.6748(2) 0.87630(11) 0.0287(3) Uani 1.000000 .
C7ba C 0.15334(7) -0.00363(18) 0.66905(10) 0.0246(3) Uani 1.000000 .
C8ba C 0.28820(7) 0.07014(18) 0.83068(10) 0.0246(3) Uani 1.000000 .
C9ba C 0.44034(6) 0.4948(2) 0.70046(10) 0.0271(3) Uani 1.000000 .
C0ca C 0.11387(6) 0.39872(18) 0.75512(10) 0.0227(3) Uani 1.000000 .
C1ca C 0.44573(8) 0.6518(2) 0.63864(12) 0.0335(4) Uani 1.000000 .
C2ca C 0.30640(7) 0.17605(19) 0.59238(10) 0.0242(3) Uani 1.000000 .
C0aa C 0.08114(7) 0.5442(2) 0.80194(12) 0.0301(3) Uani 1.000000 .
C9aa C 0.41257(7) 0.2673(2) 0.90219(11) 0.0270(3) Uani 1.000000 .
C2 C 0.46103(7) 0.3502(3) 0.63769(12) 0.0345(4) Uani 1.000000 .
H2a H 0.4350(9) 0.345(3) 0.5725(14) 0.025(4) Uiso 1.000000 .
H7ba H 0.1406(10) 0.020(3) 0.5978(15) 0.035(5) Uiso 1.000000 .
H6ba H 0.4193(9) 0.754(3) 0.9277(15) 0.030(5) Uiso 1.000000 .
H1ca H 0.4243(11) 0.742(3) 0.6681(17) 0.040(6) Uiso 1.000000 .
H8ba H 0.2997(8) -0.036(3) 0.7930(13) 0.023(4) Uiso 1.000000 .
H1cb H 0.4888(12) 0.679(3) 0.6341(16) 0.044(6) Uiso 1.000000 .
H0ca H 0.0887(8) 0.294(3) 0.7686(13) 0.023(4) Uiso 1.000000 .
H2ca H 0.2927(8) 0.223(3) 0.5283(13) 0.023(4) Uiso 1.000000 .
H2cb H 0.3550(10) 0.160(3) 0.5902(15) 0.037(5) Uiso 1.000000 .
H9aa H 0.4539(10) 0.244(3) 0.8763(15) 0.031(5) Uiso 1.000000 .
H0ab H 0.1058(10) 0.637(3) 0.7886(15) 0.034(5) Uiso 1.000000 .
H2b H 0.4582(10) 0.258(3) 0.6767(18) 0.038(6) Uiso 1.000000 .
H7aa H 0.3245(9) 0.634(2) 0.8610(14) 0.024(4) Uiso 1.000000 .
H2c H 0.5081(11) 0.362(3) 0.6202(15) 0.039(5) Uiso 1.000000 .
H9ab H 0.4203(10) 0.360(3) 0.9517(16) 0.037(5) Uiso 1.000000 .
H8bb H 0.3080(10) 0.051(3) 0.9020(16) 0.036(5) Uiso 1.000000 .
H0ac H 0.0339(11) 0.549(3) 0.7776(17) 0.044(6) Uiso 1.000000 .
H9ac H 0.3976(11) 0.170(3) 0.9400(18) 0.046(6) Uiso 1.000000 .
H0ad H 0.0840(11) 0.538(3) 0.8764(17) 0.041(5) Uiso 1.000000 .
H2cc H 0.2855(11) 0.065(3) 0.6029(16) 0.036(5) Uiso 1.000000 .
H1cc H 0.4306(11) 0.641(3) 0.5709(17) 0.037(5) Uiso 1.000000 .
H7bb H 0.1399(9) -0.113(3) 0.6984(13) 0.024(4) Uiso 1.000000 .


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
O0aa C2aa 1.4034(14) . ?
O C4aa 1.3585(16) . ?
O C8aa 1.4370(16) . ?
O2aa C3aa 1.3571(17) . ?
O2aa C0ca 1.4604(15) . ?
O3aa C3aa 1.1958(16) . ?
O4aa C1aa 1.2044(16) . ?
O5aa C6aa 1.2134(18) . ?
O6aa C6aa 1.346(2) . ?
O6aa C9ba 1.4795(15) . ?
O1aa C4aa 1.2010(18) . ?
C1aa C8aa 1.5431(18) . ?
C1aa C 1.5349(18) . ?
C2aa C4aa 1.5332(18) . ?
C2aa C5aa 1.6191(16) . ?
C2aa C2ba 1.5614(18) . ?
C3aa C4ba 1.5283(16) . ?
C5aa C7aa 1.525(2) . ?
C5aa C1ba 1.5321(19) . ?
C5aa C9ba 1.5739(18) . ?
C6aa C6ba 1.470(2) . ?
C7aa C6ba 1.3280(19) . ?
C8aa C4ba 1.5189(17) . ?
C8aa C0ca 1.5440(17) . ?
C C1 1.510(2) . ?
C C5ba 1.5167(17) . ?
C C8ba 1.5739(18) . ?
C0ba C1ba 1.3399(19) . ?
C0ba C2ba 1.5217(16) . ?
C0ba C8ba 1.499(2) . ?
C1ba C9aa 1.5044(16) . ?
C2ba C4ba 1.5537(16) . ?
C2ba C2ca 1.5327(17) . ?
C4ba C5ba 1.5269(18) . ?
C5ba C7ba 1.3254(19) . ?
C9ba C1ca 1.531(2) . ?
C9ba C2 1.513(2) . ?
C0ca C0aa 1.506(2) . ?

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
C8aa O C4aa 117.73(10) . . ?
C0ca O2aa C3aa 110.60(10) . . ?
C9ba O6aa C6aa 118.58(12) . . ?
C8aa C1aa O4aa 124.58(13) . . ?
C C1aa O4aa 128.19(12) . . ?
C C1aa C8aa 107.22(10) . . ?
C4aa C2aa O0aa 107.41(10) . . ?
C5aa C2aa O0aa 114.71(10) . . ?
C5aa C2aa C4aa 106.56(10) . . ?
C2ba C2aa O0aa 110.22(10) . . ?
C2ba C2aa C4aa 111.82(10) . . ?
C2ba C2aa C5aa 106.15(10) . . ?
O3aa C3aa O2aa 121.93(11) . . ?
C4ba C3aa O2aa 108.72(11) . . ?
C4ba C3aa O3aa 129.31(13) . . ?
O1aa C4aa O 119.82(13) . . ?
C2aa C4aa O 118.76(11) . . ?
C2aa C4aa O1aa 121.06(12) . . ?
C7aa C5aa C2aa 113.36(11) . . ?
C1ba C5aa C2aa 101.55(10) . . ?
C1ba C5aa C7aa 106.13(10) . . ?
C9ba C5aa C2aa 113.89(10) . . ?
C9ba C5aa C7aa 106.54(11) . . ?
C9ba C5aa C1ba 115.28(12) . . ?
O6aa C6aa O5aa 118.65(16) . . ?
C6ba C6aa O5aa 124.05(16) . . ?
C6ba C6aa O6aa 117.20(12) . . ?
C6ba C7aa C5aa 122.61(14) . . ?
C1aa C8aa O 113.22(10) . . ?
C4ba C8aa O 114.76(10) . . ?
C4ba C8aa C1aa 105.32(11) . . ?
C0ca C8aa O 108.85(11) . . ?
C0ca C8aa C1aa 112.91(11) . . ?
C0ca C8aa C4ba 101.23(10) . . ?
C1 C C1aa 113.88(11) . . ?
C5ba C C1aa 101.53(10) . . ?
C5ba C C1 117.42(11) . . ?
C8ba C C1aa 105.76(10) . . ?
C8ba C C1 111.47(11) . . ?
C8ba C C5ba 105.63(11) . . ?
C2ba C0ba C1ba 113.15(12) . . ?
C8ba C0ba C1ba 127.78(12) . . ?
C8ba C0ba C2ba 119.03(11) . . ?
C0ba C1ba C5aa 112.76(11) . . ?
C9aa C1ba C5aa 122.22(12) . . ?
C9aa C1ba C0ba 124.98(13) . . ?
C0ba C2ba C2aa 102.33(10) . . ?
C4ba C2ba C2aa 110.53(10) . . ?
C4ba C2ba C0ba 108.19(10) . . ?
C2ca C2ba C2aa 114.29(11) . . ?
C2ca C2ba C0ba 111.20(11) . . ?
C2ca C2ba C4ba 109.94(10) . . ?
C8aa C4ba C3aa 103.44(10) . . ?
C2ba C4ba C3aa 119.07(11) . . ?
C2ba C4ba C8aa 111.39(10) . . ?
C5ba C4ba C3aa 110.71(10) . . ?
C5ba C4ba C8aa 100.01(10) . . ?
C5ba C4ba C2ba 110.37(10) . . ?
C4ba C5ba C 105.17(11) . . ?
C7ba C5ba C 127.74(13) . . ?
C7ba C5ba C4ba 127.00(12) . . ?
C7aa C6ba C6aa 120.67(15) . . ?
C0ba C8ba C 110.23(10) . . ?
C5aa C9ba O6aa 107.27(10) . . ?
C1ca C9ba O6aa 105.97(12) . . ?
C1ca C9ba C5aa 115.59(13) . . ?
C2 C9ba O6aa 102.85(11) . . ?
C2 C9ba C5aa 113.95(13) . . ?
C2 C9ba C1ca 110.04(13) . . ?
C8aa C0ca O2aa 103.48(10) . . ?
C0aa C0ca O2aa 109.91(12) . . ?
C0aa C0ca C8aa 116.97(11) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
