# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2112141'
loop_
_audit_author_name
_audit_author_address
'Xiaonian Li'
;State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botan
China
;
_audit_update_record             
;
2021-09-27 deposited with the CCDC.	2022-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H34 O5'
_chemical_formula_weight         414.52

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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   22.3405(2)
_cell_length_b                   9.06820(10)
_cell_length_c                   13.9052(2)
_cell_angle_alpha                90
_cell_angle_beta                 127.4330(10)
_cell_angle_gamma                90
_cell_volume                     2236.90(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14152
_cell_measurement_theta_min      4.081
_cell_measurement_theta_max      73.639

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.678
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21662
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.003
_diffrn_reflns_theta_max         73.958
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4389
_reflns_number_gt                4261
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_max     0.944
_reflns_Friedel_fraction_full    0.970

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1428P)²+0.7493P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1872 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(14)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         4389
_refine_ls_number_parameters     277
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1704
_refine_ls_wR_factor_gt          0.1692
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.001

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
C1 C 0.7602(3) 0.1470(8) 0.2694(4) 0.0725(18) Uani 1 1 d . . . . .
H1A H 0.7675 0.2455 0.3001 0.109 Uiso 1 1 calc R U . . .
H1B H 0.8064 0.1113 0.2873 0.109 Uiso 1 1 calc R U . . .
H1C H 0.7453 0.0841 0.3070 0.109 Uiso 1 1 calc R U . . .
C2 C 0.7312(3) 0.1645(6) 0.0650(4) 0.0520(10) Uani 1 1 d . . . . .
H2A H 0.7513 0.2621 0.0770 0.078 Uiso 1 1 calc R U . . .
H2B H 0.6917 0.1490 -0.0197 0.078 Uiso 1 1 calc R U . . .
H2C H 0.7705 0.0934 0.0933 0.078 Uiso 1 1 calc R U . . .
C3 C 0.6997(2) 0.1474(5) 0.1348(4) 0.0463(9) Uani 1 1 d . . . . .
H3 H 0.6726 0.0534 0.1117 0.056 Uiso 1 1 calc R U . . .
C4 C 0.6448(3) 0.2701(5) 0.1030(4) 0.0454(9) Uani 1 1 d . . . . .
H4A H 0.6107 0.2811 0.0157 0.054 Uiso 1 1 calc R U . . .
H4B H 0.6726 0.3616 0.1369 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5990(2) 0.2455(4) 0.1482(3) 0.0341(7) Uani 1 1 d . . . . .
C6 C 0.57357(17) 0.3571(4) 0.1858(3) 0.0275(7) Uani 1 1 d . . . . .
C7 C 0.58628(16) 0.5145(4) 0.1764(3) 0.0249(6) Uani 1 1 d . . . . .
C8 C 0.59684(16) 0.6279(3) 0.2683(3) 0.0246(6) Uani 1 1 d . . . . .
C9 C 0.51539(16) 0.6852(4) 0.2089(3) 0.0257(6) Uani 1 1 d . . . . .
H9 H 0.4961 0.7183 0.1277 0.031 Uiso 1 1 calc R U . . .
C10 C 0.46475(16) 0.5542(4) 0.1890(3) 0.0267(6) Uani 1 1 d . . . . .
H10A H 0.4394 0.5183 0.1070 0.032 Uiso 1 1 calc R U . . .
H10B H 0.4262 0.5909 0.1947 0.032 Uiso 1 1 calc R U . . .
C11 C 0.50451(17) 0.4205(4) 0.2773(3) 0.0275(6) Uani 1 1 d . . . . .
C12 C 0.53130(16) 0.3118(4) 0.2273(3) 0.0271(6) Uani 1 1 d . . . . .
C13 C 0.45080(19) 0.3466(4) 0.2956(3) 0.0335(7) Uani 1 1 d . . . . .
H13A H 0.4748 0.2618 0.3468 0.050 Uiso 1 1 calc R U . . .
H13B H 0.4059 0.3164 0.2185 0.050 Uiso 1 1 calc R U . . .
H13C H 0.4378 0.4150 0.3328 0.050 Uiso 1 1 calc R U . . .
C14 C 0.57690(18) 0.4694(4) 0.3989(3) 0.0284(7) Uani 1 1 d . . . . .
C15 C 0.63182(16) 0.5559(4) 0.3927(3) 0.0274(6) Uani 1 1 d . . . . .
H15A H 0.6723 0.4908 0.4122 0.033 Uiso 1 1 calc R U . . .
H15B H 0.6538 0.6326 0.4539 0.033 Uiso 1 1 calc R U . . .
C16 C 0.50689(18) 0.8191(4) 0.2687(3) 0.0297(7) Uani 1 1 d . . . . .
H16 H 0.5451 0.8917 0.2876 0.036 Uiso 1 1 calc R U . . .
C17 C 0.5169(2) 0.7879(4) 0.3862(3) 0.0378(8) Uani 1 1 d . . . . .
H17A H 0.5077 0.8765 0.4131 0.057 Uiso 1 1 calc R U . . .
H17B H 0.5675 0.7547 0.4473 0.057 Uiso 1 1 calc R U . . .
H17C H 0.4820 0.7130 0.3717 0.057 Uiso 1 1 calc R U . . .
C18 C 0.4296(2) 0.8897(4) 0.1765(4) 0.0362(8) Uani 1 1 d . . . . .
H18A H 0.3907 0.8219 0.1575 0.054 Uiso 1 1 calc R U . . .
H18B H 0.4239 0.9132 0.1040 0.054 Uiso 1 1 calc R U . . .
H18C H 0.4256 0.9782 0.2101 0.054 Uiso 1 1 calc R U . . .
C19 C 0.64917(16) 0.7530(4) 0.2826(3) 0.0262(6) Uani 1 1 d . . . . .
H19A H 0.6253 0.8010 0.2049 0.031 Uiso 1 1 calc R U . . .
H19B H 0.6551 0.8259 0.3388 0.031 Uiso 1 1 calc R U . . .
C20 C 0.72583(17) 0.6990(4) 0.3276(3) 0.0265(6) Uani 1 1 d . . . . .
C21 C 0.78674(17) 0.6719(4) 0.4573(3) 0.0307(7) Uani 1 1 d . . . . .
C22 C 0.84941(18) 0.5906(4) 0.4677(3) 0.0369(8) Uani 1 1 d . . . . .
H22A H 0.8475 0.4858 0.4797 0.044 Uiso 1 1 calc R U . . .
H22B H 0.8983 0.6286 0.5343 0.044 Uiso 1 1 calc R U . . .
C23 C 0.83416(19) 0.6200(5) 0.3469(3) 0.0372(8) Uani 1 1 d . . . . .
H23A H 0.8692 0.6923 0.3557 0.045 Uiso 1 1 calc R U . . .
H23B H 0.8384 0.5300 0.3137 0.045 Uiso 1 1 calc R U . . .
C24 C 0.75409(17) 0.6784(4) 0.2667(3) 0.0294(7) Uani 1 1 d . . . . .
C25 C 0.7190(2) 0.7139(5) 0.1379(3) 0.0389(8) Uani 1 1 d . . . . .
H25A H 0.6696 0.7542 0.0998 0.058 Uiso 1 1 calc R U . . .
H25B H 0.7152 0.6257 0.0963 0.058 Uiso 1 1 calc R U . . .
H25C H 0.7497 0.7847 0.1345 0.058 Uiso 1 1 calc R U . . .
O1 O 0.58253(15) 0.1090(3) 0.1481(3) 0.0392(6) Uani 1 1 d . . . . .
O2 O 0.51469(13) 0.1782(3) 0.2246(2) 0.0338(5) Uani 1 1 d . . . . .
H2O H 0.5334 0.1277 0.2002 0.041 Uiso 1 1 calc R U . . .
O3 O 0.59007(14) 0.4351(3) 0.4947(2) 0.0372(6) Uani 1 1 d . . . . .
O4 O 0.58774(12) 0.5573(3) 0.09406(18) 0.0281(5) Uani 1 1 d . . . . .
O5 O 0.78796(14) 0.7123(3) 0.5427(2) 0.0395(6) 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
C1 C3 1.502(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.513(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.509(6) . ?
C3 H3 0.9800 . ?
C4 C5 1.507(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O1 1.291(4) . ?
C5 C6 1.408(5) . ?
C6 C12 1.433(4) . ?
C6 C7 1.477(4) . ?
C7 O4 1.228(4) . ?
C7 C8 1.543(4) . ?
C8 C15 1.545(4) . ?
C8 C19 1.552(4) . ?
C8 C9 1.561(4) . ?
C9 C10 1.545(4) . ?
C9 C16 1.547(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.563(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C13 1.524(4) . ?
C11 C12 1.523(5) . ?
C11 C14 1.532(4) . ?
C12 O2 1.261(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O3 1.217(4) . ?
C14 C15 1.502(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C18 1.532(5) . ?
C16 C17 1.534(4) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.504(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C24 1.342(4) . ?
C20 C21 1.477(4) . ?
C21 O5 1.227(4) . ?
C21 C22 1.510(5) . ?
C22 C23 1.521(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.516(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.490(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
O2 H2O 0.8200 . ?
O2 H2O 0.8200 . ?

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
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 C4 108.7(4) . . ?
C1 C3 C2 112.6(4) . . ?
C4 C3 C2 110.4(4) . . ?
C1 C3 H3 108.3 . . ?
C4 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
C3 C4 C5 114.0(4) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
O1 C5 C6 120.7(3) . . ?
O1 C5 C4 114.0(3) . . ?
C6 C5 C4 125.3(3) . . ?
C5 C6 C12 117.2(3) . . ?
C5 C6 C7 121.3(3) . . ?
C12 C6 C7 121.4(3) . . ?
O4 C7 C6 120.2(3) . . ?
O4 C7 C8 119.0(3) . . ?
C6 C7 C8 120.8(3) . . ?
C7 C8 C15 111.4(3) . . ?
C7 C8 C19 108.5(2) . . ?
C15 C8 C19 109.7(2) . . ?
C7 C8 C9 104.0(2) . . ?
C15 C8 C9 111.5(2) . . ?
C19 C8 C9 111.7(3) . . ?
C10 C9 C16 112.6(2) . . ?
C10 C9 C8 109.3(3) . . ?
C16 C9 C8 117.5(2) . . ?
C10 C9 H9 105.5 . . ?
C16 C9 H9 105.5 . . ?
C8 C9 H9 105.5 . . ?
C9 C10 C11 116.8(2) . . ?
C9 C10 H10A 108.1 . . ?
C11 C10 H10A 108.1 . . ?
C9 C10 H10B 108.1 . . ?
C11 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
C13 C11 C12 111.1(3) . . ?
C13 C11 C14 110.7(2) . . ?
C12 C11 C14 104.3(3) . . ?
C13 C11 C10 110.1(3) . . ?
C12 C11 C10 109.6(2) . . ?
C14 C11 C10 110.9(3) . . ?
O2 C12 C6 121.2(3) . . ?
O2 C12 C11 116.4(3) . . ?
C6 C12 C11 122.4(3) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 C15 122.2(3) . . ?
O3 C14 C11 121.6(3) . . ?
C15 C14 C11 116.1(2) . . ?
C14 C15 C8 114.2(2) . . ?
C14 C15 H15A 108.7 . . ?
C8 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C8 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C18 C16 C17 109.2(3) . . ?
C18 C16 C9 108.8(3) . . ?
C17 C16 C9 116.2(3) . . ?
C18 C16 H16 107.4 . . ?
C17 C16 H16 107.4 . . ?
C9 C16 H16 107.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C8 113.2(3) . . ?
C20 C19 H19A 108.9 . . ?
C8 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C8 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C24 C20 C21 108.1(3) . . ?
C24 C20 C19 129.6(3) . . ?
C21 C20 C19 122.2(3) . . ?
O5 C21 C20 126.5(3) . . ?
O5 C21 C22 125.4(3) . . ?
C20 C21 C22 108.1(3) . . ?
C21 C22 C23 103.7(3) . . ?
C21 C22 H22A 111.0 . . ?
C23 C22 H22A 111.0 . . ?
C21 C22 H22B 111.0 . . ?
C23 C22 H22B 111.0 . . ?
H22A C22 H22B 109.0 . . ?
C24 C23 C22 104.2(3) . . ?
C24 C23 H23A 110.9 . . ?
C22 C23 H23A 110.9 . . ?
C24 C23 H23B 110.9 . . ?
C22 C23 H23B 110.9 . . ?
H23A C23 H23B 108.9 . . ?
C20 C24 C25 128.6(3) . . ?
C20 C24 C23 112.5(3) . . ?
C25 C24 C23 118.9(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C12 O2 H2O 109.5 . . ?
C12 O2 H2O 109.5 . . ?
H2O O2 H2O 0.0 . . ?

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
C1 C3 C4 C5 -67.8(5) . . . . ?
C2 C3 C4 C5 168.2(4) . . . . ?
C3 C4 C5 O1 -34.1(5) . . . . ?
C3 C4 C5 C6 147.1(4) . . . . ?
O1 C5 C6 C12 2.0(5) . . . . ?
C4 C5 C6 C12 -179.3(3) . . . . ?
O1 C5 C6 C7 -174.6(3) . . . . ?
C4 C5 C6 C7 4.0(6) . . . . ?
C5 C6 C7 O4 32.0(5) . . . . ?
C12 C6 C7 O4 -144.5(3) . . . . ?
C5 C6 C7 C8 -148.8(3) . . . . ?
C12 C6 C7 C8 34.7(4) . . . . ?
O4 C7 C8 C15 -152.0(3) . . . . ?
C6 C7 C8 C15 28.9(4) . . . . ?
O4 C7 C8 C19 -31.2(3) . . . . ?
C6 C7 C8 C19 149.6(3) . . . . ?
O4 C7 C8 C9 87.8(3) . . . . ?
C6 C7 C8 C9 -91.4(3) . . . . ?
C7 C8 C9 C10 59.3(3) . . . . ?
C15 C8 C9 C10 -60.8(3) . . . . ?
C19 C8 C9 C10 176.1(2) . . . . ?
C7 C8 C9 C16 -170.8(3) . . . . ?
C15 C8 C9 C16 69.0(3) . . . . ?
C19 C8 C9 C16 -54.1(3) . . . . ?
C16 C9 C10 C11 -104.8(3) . . . . ?
C8 C9 C10 C11 27.7(3) . . . . ?
C9 C10 C11 C13 148.9(3) . . . . ?
C9 C10 C11 C12 -88.6(3) . . . . ?
C9 C10 C11 C14 26.0(3) . . . . ?
C5 C6 C12 O2 -3.2(4) . . . . ?
C7 C6 C12 O2 173.4(3) . . . . ?
C5 C6 C12 C11 176.3(3) . . . . ?
C7 C6 C12 C11 -7.0(4) . . . . ?
C13 C11 C12 O2 -9.4(4) . . . . ?
C14 C11 C12 O2 109.9(3) . . . . ?
C10 C11 C12 O2 -131.3(3) . . . . ?
C13 C11 C12 C6 171.0(3) . . . . ?
C14 C11 C12 C6 -69.7(3) . . . . ?
C10 C11 C12 C6 49.1(4) . . . . ?
C13 C11 C14 O3 7.9(5) . . . . ?
C12 C11 C14 O3 -111.7(3) . . . . ?
C10 C11 C14 O3 130.4(3) . . . . ?
C13 C11 C14 C15 -174.7(3) . . . . ?
C12 C11 C14 C15 65.7(4) . . . . ?
C10 C11 C14 C15 -52.2(4) . . . . ?
O3 C14 C15 C8 -162.6(3) . . . . ?
C11 C14 C15 C8 20.0(4) . . . . ?
C7 C8 C15 C14 -78.5(3) . . . . ?
C19 C8 C15 C14 161.4(3) . . . . ?
C9 C8 C15 C14 37.2(4) . . . . ?
C10 C9 C16 C18 -71.1(3) . . . . ?
C8 C9 C16 C18 160.6(3) . . . . ?
C10 C9 C16 C17 52.6(4) . . . . ?
C8 C9 C16 C17 -75.6(4) . . . . ?
C7 C8 C19 C20 -60.0(3) . . . . ?
C15 C8 C19 C20 61.8(3) . . . . ?
C9 C8 C19 C20 -174.0(2) . . . . ?
C8 C19 C20 C24 104.1(4) . . . . ?
C8 C19 C20 C21 -81.7(4) . . . . ?
C24 C20 C21 O5 161.7(3) . . . . ?
C19 C20 C21 O5 -13.7(5) . . . . ?
C24 C20 C21 C22 -16.0(4) . . . . ?
C19 C20 C21 C22 168.7(3) . . . . ?
O5 C21 C22 C23 -158.7(3) . . . . ?
C20 C21 C22 C23 19.0(4) . . . . ?
C21 C22 C23 C24 -14.9(4) . . . . ?
C21 C20 C24 C25 -169.9(3) . . . . ?
C19 C20 C24 C25 5.0(6) . . . . ?
C21 C20 C24 C23 6.0(4) . . . . ?
C19 C20 C24 C23 -179.1(3) . . . . ?
C22 C23 C24 C20 6.1(4) . . . . ?
C22 C23 C24 C25 -177.7(3) . . . . ?
C6 C12 O2 H2O 2.9 . . . . ?
C11 C12 O2 H2O -176.7 . . . . ?

_refine_diff_density_max         0.617
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_ZN1_35_7_0m
_database_code_depnum_ccdc_archive 'CCDC 2040860'
loop_
_audit_author_name
_audit_author_address
'Xiaonian Li'
;State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botan
China
;
_audit_update_record             
;
2021-09-27 deposited with the CCDC.	2022-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H40 O6'
_chemical_formula_weight         460.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.3578(3)
_cell_length_b                   11.4643(3)
_cell_length_c                   23.4068(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2511.10(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    157(2)
_cell_measurement_reflns_used    9027
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      79.20

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.248
_exptl_absorpt_coefficient_mu    0.681
_shelx_estimated_absorpt_T_min   0.811
_shelx_estimated_absorpt_T_max   0.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      157(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43768
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.777
_diffrn_reflns_theta_max         79.219
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5397
_reflns_number_gt                5339
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.996

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0744P)²+1.0231P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2268 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(5)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         5397
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1319
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.002

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 0.6731(2) 0.33383(19) 0.72896(8) 0.0362(5) Uani 1 1 d . . . . .
O2 O 0.5804(3) 0.71505(19) 0.66484(11) 0.0482(6) Uani 1 1 d . . . . .
H2O H 0.5595 0.7331 0.6986 0.058 Uiso 1 1 calc R U . . .
O3 O 0.3861(2) 0.57310(18) 0.51930(9) 0.0372(5) Uani 1 1 d . . . . .
O4 O 0.4942(2) 0.39357(17) 0.54715(8) 0.0317(4) Uani 1 1 d . . . . .
O5 O 0.75139(18) 0.19308(16) 0.53830(7) 0.0255(3) Uani 1 1 d . . . . .
H5O H 0.673(4) 0.193(3) 0.5184(11) 0.038 Uiso 1 1 calc R U . . .
O6 O 1.01269(18) 0.31325(16) 0.53304(7) 0.0260(4) Uani 1 1 d . . . . .
H6O H 0.9480 0.2648 0.5256 0.039 Uiso 1 1 calc R U . . .
C1 C 1.1384(3) 0.4153(3) 0.60455(13) 0.0358(6) Uani 1 1 d . . . . .
H1A H 1.2247 0.4097 0.5810 0.054 Uiso 1 1 calc R U . . .
H1B H 1.1652 0.4173 0.6450 0.054 Uiso 1 1 calc R U . . .
H1C H 1.0863 0.4867 0.5948 0.054 Uiso 1 1 calc R U . . .
C2 C 1.0438(2) 0.3102(2) 0.59352(10) 0.0253(5) Uani 1 1 d . . . . .
C3 C 0.9052(2) 0.3091(2) 0.62931(9) 0.0218(4) Uani 1 1 d . . . . .
H3 H 0.9315 0.3312 0.6693 0.026 Uiso 1 1 calc R U . . .
C4 C 0.7931(2) 0.3963(2) 0.60869(10) 0.0209(4) Uani 1 1 d . . . . .
H4A H 0.7944 0.3985 0.5664 0.025 Uiso 1 1 calc R U . . .
H4B H 0.8191 0.4750 0.6227 0.025 Uiso 1 1 calc R U . . .
C5 C 0.6379(2) 0.36653(19) 0.62929(10) 0.0205(4) Uani 1 1 d . . . . .
C6 C 0.5414(2) 0.4423(2) 0.59310(10) 0.0237(5) Uani 1 1 d . . . . .
C7 C 0.5154(3) 0.5593(2) 0.60524(11) 0.0287(5) Uani 1 1 d . . . . .
C8 C 0.4349(3) 0.6243(3) 0.56330(12) 0.0325(6) Uani 1 1 d . . . . .
C9 C 0.4023(4) 0.7517(3) 0.57013(15) 0.0404(7) Uani 1 1 d . . . . .
H9A H 0.4936 0.7954 0.5705 0.049 Uiso 1 1 calc R U . . .
H9B H 0.3559 0.7636 0.6077 0.049 Uiso 1 1 calc R U . . .
C10 C 0.3058(4) 0.8038(3) 0.52362(16) 0.0456(7) Uani 1 1 d . . . . .
H10 H 0.2221 0.7507 0.5182 0.055 Uiso 1 1 calc R U . . .
C11 C 0.3830(5) 0.8150(4) 0.4672(2) 0.0639(11) Uani 1 1 d . . . . .
H11A H 0.4167 0.7381 0.4549 0.096 Uiso 1 1 calc R U . . .
H11B H 0.4649 0.8676 0.4717 0.096 Uiso 1 1 calc R U . . .
H11C H 0.3176 0.8468 0.4384 0.096 Uiso 1 1 calc R U . . .
C12 C 0.6372(2) 0.4025(2) 0.69227(10) 0.0238(5) Uani 1 1 d . . . . .
C13 C 0.5932(3) 0.5267(2) 0.70916(11) 0.0291(5) Uani 1 1 d . . . . .
C14 C 0.5681(3) 0.6099(2) 0.65863(13) 0.0315(5) Uani 1 1 d . . . . .
C15 C 0.2507(5) 0.9215(3) 0.5438(2) 0.0615(10) Uani 1 1 d . . . . .
H15A H 0.3316 0.9737 0.5510 0.092 Uiso 1 1 calc R U . . .
H15B H 0.1958 0.9112 0.5791 0.092 Uiso 1 1 calc R U . . .
H15C H 0.1890 0.9554 0.5143 0.092 Uiso 1 1 calc R U . . .
C16 C 0.4441(3) 0.5129(3) 0.73779(14) 0.0421(7) Uani 1 1 d . . . . .
H16A H 0.3788 0.4736 0.7113 0.063 Uiso 1 1 calc R U . . .
H16B H 0.4060 0.5900 0.7474 0.063 Uiso 1 1 calc R U . . .
H16C H 0.4536 0.4663 0.7727 0.063 Uiso 1 1 calc R U . . .
C17 C 0.6992(3) 0.5800(3) 0.75223(12) 0.0381(6) Uani 1 1 d . . . . .
H17A H 0.6653 0.6589 0.7628 0.046 Uiso 1 1 calc R U . . .
H17B H 0.6991 0.5317 0.7873 0.046 Uiso 1 1 calc R U . . .
C18 C 0.8504(3) 0.5895(3) 0.73058(12) 0.0343(6) Uani 1 1 d . . . . .
H18 H 0.9015 0.5183 0.7268 0.041 Uiso 1 1 calc R U . . .
C19 C 0.9208(3) 0.6862(3) 0.71612(12) 0.0368(6) Uani 1 1 d . . . . .
C20 C 1.0725(4) 0.6798(4) 0.69537(18) 0.0571(10) Uani 1 1 d . . . . .
H20A H 1.1068 0.5993 0.6982 0.086 Uiso 1 1 calc R U . . .
H20B H 1.1327 0.7306 0.7189 0.086 Uiso 1 1 calc R U . . .
H20C H 1.0768 0.7055 0.6555 0.086 Uiso 1 1 calc R U . . .
C21 C 0.8603(4) 0.8074(3) 0.71853(18) 0.0523(9) Uani 1 1 d . . . . .
H21A H 0.8488 0.8376 0.6796 0.078 Uiso 1 1 calc R U . . .
H21B H 0.9255 0.8581 0.7399 0.078 Uiso 1 1 calc R U . . .
H21C H 0.7672 0.8056 0.7376 0.078 Uiso 1 1 calc R U . . .
C22 C 0.6014(3) 0.2353(2) 0.62209(11) 0.0251(5) Uani 1 1 d . . . . .
H22A H 0.5762 0.2032 0.6601 0.030 Uiso 1 1 calc R U . . .
H22B H 0.5156 0.2287 0.5976 0.030 Uiso 1 1 calc R U . . .
C23 C 0.7201(3) 0.1591(2) 0.59624(10) 0.0235(5) Uani 1 1 d . . . . .
C24 C 0.6727(3) 0.0317(2) 0.59670(12) 0.0336(6) Uani 1 1 d . . . . .
H24A H 0.5839 0.0236 0.5749 0.050 Uiso 1 1 calc R U . . .
H24B H 0.6567 0.0065 0.6362 0.050 Uiso 1 1 calc R U . . .
H24C H 0.7472 -0.0168 0.5793 0.050 Uiso 1 1 calc R U . . .
C25 C 0.8562(3) 0.1785(2) 0.63047(10) 0.0236(5) Uani 1 1 d . . . . .
H25 H 0.8366 0.1566 0.6711 0.028 Uiso 1 1 calc R U . . .
C26 C 0.9876(3) 0.1075(2) 0.60978(11) 0.0304(5) Uani 1 1 d . . . . .
H26A H 1.0072 0.0417 0.6360 0.036 Uiso 1 1 calc R U . . .
H26B H 0.9710 0.0762 0.5709 0.036 Uiso 1 1 calc R U . . .
C27 C 1.1124(3) 0.1942(3) 0.60968(12) 0.0326(6) Uani 1 1 d . . . . .
H27A H 1.1574 0.1988 0.6479 0.039 Uiso 1 1 calc R U . . .
H27B H 1.1857 0.1714 0.5813 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.212(3) . ?
O2 C14 1.220(4) . ?
O2 H2O 0.8400 . ?
O3 C8 1.270(4) . ?
O4 C6 1.290(3) . ?
O5 C23 1.441(3) . ?
O5 H5O 0.87(4) . ?
O6 C2 1.446(3) . ?
O6 H6O 0.8400 . ?
C1 C2 1.517(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C27 1.524(4) . ?
C2 C3 1.544(3) . ?
C3 C4 1.527(3) . ?
C3 C25 1.566(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.569(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.512(3) . ?
C5 C12 1.531(3) . ?
C5 C22 1.552(3) . ?
C6 C7 1.392(4) . ?
C7 C8 1.444(4) . ?
C7 C14 1.464(4) . ?
C8 C9 1.501(4) . ?
C9 C10 1.535(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.511(6) . ?
C10 C15 1.520(5) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.534(3) . ?
C13 C14 1.537(4) . ?
C13 C17 1.541(4) . ?
C13 C16 1.556(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.507(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.334(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.501(5) . ?
C19 C21 1.502(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.536(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C25 1.521(3) . ?
C23 C24 1.527(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.552(3) . ?
C25 H25 1.0000 . ?
C26 C27 1.534(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O2 H2O 109.5 . . ?
C23 O5 H5O 109.5 . . ?
C2 O6 H6O 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O6 C2 C1 105.4(2) . . ?
O6 C2 C27 110.4(2) . . ?
C1 C2 C27 113.9(2) . . ?
O6 C2 C3 111.26(18) . . ?
C1 C2 C3 113.9(2) . . ?
C27 C2 C3 102.2(2) . . ?
C4 C3 C2 113.54(19) . . ?
C4 C3 C25 115.52(19) . . ?
C2 C3 C25 105.26(18) . . ?
C4 C3 H3 107.4 . . ?
C2 C3 H3 107.4 . . ?
C25 C3 H3 107.4 . . ?
C3 C4 C5 113.34(18) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C12 112.46(19) . . ?
C6 C5 C22 111.41(19) . . ?
C12 C5 C22 111.39(19) . . ?
C6 C5 C4 104.81(18) . . ?
C12 C5 C4 103.97(18) . . ?
C22 C5 C4 112.41(19) . . ?
O4 C6 C7 121.8(2) . . ?
O4 C6 C5 115.0(2) . . ?
C7 C6 C5 122.9(2) . . ?
C6 C7 C8 116.7(2) . . ?
C6 C7 C14 119.8(2) . . ?
C8 C7 C14 123.5(2) . . ?
O3 C8 C7 120.0(3) . . ?
O3 C8 C9 117.6(3) . . ?
C7 C8 C9 122.4(3) . . ?
C8 C9 C10 115.0(3) . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C15 111.0(3) . . ?
C11 C10 C9 111.8(3) . . ?
C15 C10 C9 108.9(3) . . ?
C11 C10 H10 108.3 . . ?
C15 C10 H10 108.3 . . ?
C9 C10 H10 108.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 C5 120.4(2) . . ?
O1 C12 C13 119.6(2) . . ?
C5 C12 C13 120.0(2) . . ?
C12 C13 C14 114.7(2) . . ?
C12 C13 C17 111.3(2) . . ?
C14 C13 C17 110.8(2) . . ?
C12 C13 C16 104.9(2) . . ?
C14 C13 C16 104.9(2) . . ?
C17 C13 C16 109.6(2) . . ?
O2 C14 C7 121.7(3) . . ?
O2 C14 C13 120.5(3) . . ?
C7 C14 C13 117.5(2) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C13 114.4(2) . . ?
C18 C17 H17A 108.7 . . ?
C13 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C13 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 127.5(3) . . ?
C19 C18 H18 116.2 . . ?
C17 C18 H18 116.2 . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 C21 125.0(3) . . ?
C20 C19 C21 114.4(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C5 115.8(2) . . ?
C23 C22 H22A 108.3 . . ?
C5 C22 H22A 108.3 . . ?
C23 C22 H22B 108.3 . . ?
C5 C22 H22B 108.3 . . ?
H22A C22 H22B 107.4 . . ?
O5 C23 C25 106.62(19) . . ?
O5 C23 C24 108.91(19) . . ?
C25 C23 C24 112.3(2) . . ?
O5 C23 C22 111.4(2) . . ?
C25 C23 C22 108.37(19) . . ?
C24 C23 C22 109.3(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 C26 115.0(2) . . ?
C23 C25 C3 112.03(18) . . ?
C26 C25 C3 105.33(19) . . ?
C23 C25 H25 108.1 . . ?
C26 C25 H25 108.1 . . ?
C3 C25 H25 108.1 . . ?
C27 C26 C25 105.3(2) . . ?
C27 C26 H26A 110.7 . . ?
C25 C26 H26A 110.7 . . ?
C27 C26 H26B 110.7 . . ?
C25 C26 H26B 110.7 . . ?
H26A C26 H26B 108.8 . . ?
C2 C27 C26 104.18(19) . . ?
C2 C27 H27A 110.9 . . ?
C26 C27 H27A 110.9 . . ?
C2 C27 H27B 110.9 . . ?
C26 C27 H27B 110.9 . . ?
H27A C27 H27B 108.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 C2 C3 C4 -44.6(3) . . . . ?
C1 C2 C3 C4 74.3(3) . . . . ?
C27 C2 C3 C4 -162.5(2) . . . . ?
O6 C2 C3 C25 82.7(2) . . . . ?
C1 C2 C3 C25 -158.4(2) . . . . ?
C27 C2 C3 C25 -35.2(2) . . . . ?
C2 C3 C4 C5 159.52(19) . . . . ?
C25 C3 C4 C5 37.8(3) . . . . ?
C3 C4 C5 C6 -166.12(19) . . . . ?
C3 C4 C5 C12 75.7(2) . . . . ?
C3 C4 C5 C22 -45.0(3) . . . . ?
C12 C5 C6 O4 -154.6(2) . . . . ?
C22 C5 C6 O4 -28.7(3) . . . . ?
C4 C5 C6 O4 93.1(2) . . . . ?
C12 C5 C6 C7 31.1(3) . . . . ?
C22 C5 C6 C7 156.9(2) . . . . ?
C4 C5 C6 C7 -81.2(3) . . . . ?
O4 C6 C7 C8 -1.1(4) . . . . ?
C5 C6 C7 C8 172.8(2) . . . . ?
O4 C6 C7 C14 178.4(2) . . . . ?
C5 C6 C7 C14 -7.6(4) . . . . ?
C6 C7 C8 O3 3.2(4) . . . . ?
C14 C7 C8 O3 -176.3(3) . . . . ?
C6 C7 C8 C9 -178.4(3) . . . . ?
C14 C7 C8 C9 2.1(4) . . . . ?
O3 C8 C9 C10 3.0(4) . . . . ?
C7 C8 C9 C10 -175.4(3) . . . . ?
C8 C9 C10 C11 -71.7(4) . . . . ?
C8 C9 C10 C15 165.2(3) . . . . ?
C6 C5 C12 O1 158.5(2) . . . . ?
C22 C5 C12 O1 32.7(3) . . . . ?
C4 C5 C12 O1 -88.6(3) . . . . ?
C6 C5 C12 C13 -22.5(3) . . . . ?
C22 C5 C12 C13 -148.3(2) . . . . ?
C4 C5 C12 C13 90.4(2) . . . . ?
O1 C12 C13 C14 172.7(2) . . . . ?
C5 C12 C13 C14 -6.3(3) . . . . ?
O1 C12 C13 C17 45.8(3) . . . . ?
C5 C12 C13 C17 -133.2(2) . . . . ?
O1 C12 C13 C16 -72.7(3) . . . . ?
C5 C12 C13 C16 108.3(2) . . . . ?
C6 C7 C14 O2 161.1(3) . . . . ?
C8 C7 C14 O2 -19.4(4) . . . . ?
C6 C7 C14 C13 -25.0(3) . . . . ?
C8 C7 C14 C13 154.5(2) . . . . ?
C12 C13 C14 O2 -155.2(3) . . . . ?
C17 C13 C14 O2 -28.0(4) . . . . ?
C16 C13 C14 O2 90.3(3) . . . . ?
C12 C13 C14 C7 30.9(3) . . . . ?
C17 C13 C14 C7 158.0(2) . . . . ?
C16 C13 C14 C7 -83.7(3) . . . . ?
C12 C13 C17 C18 60.1(3) . . . . ?
C14 C13 C17 C18 -68.9(3) . . . . ?
C16 C13 C17 C18 175.8(3) . . . . ?
C13 C17 C18 C19 108.6(3) . . . . ?
C17 C18 C19 C20 179.8(3) . . . . ?
C17 C18 C19 C21 -0.3(5) . . . . ?
C6 C5 C22 C23 116.8(2) . . . . ?
C12 C5 C22 C23 -116.7(2) . . . . ?
C4 C5 C22 C23 -0.5(3) . . . . ?
C5 C22 C23 O5 -64.4(3) . . . . ?
C5 C22 C23 C25 52.6(3) . . . . ?
C5 C22 C23 C24 175.2(2) . . . . ?
O5 C23 C25 C26 -60.0(3) . . . . ?
C24 C23 C25 C26 59.2(3) . . . . ?
C22 C23 C25 C26 -180.0(2) . . . . ?
O5 C23 C25 C3 60.2(2) . . . . ?
C24 C23 C25 C3 179.40(19) . . . . ?
C22 C23 C25 C3 -59.8(2) . . . . ?
C4 C3 C25 C23 15.1(3) . . . . ?
C2 C3 C25 C23 -111.0(2) . . . . ?
C4 C3 C25 C26 140.8(2) . . . . ?
C2 C3 C25 C26 14.7(2) . . . . ?
C23 C25 C26 C27 135.2(2) . . . . ?
C3 C25 C26 C27 11.3(2) . . . . ?
O6 C2 C27 C26 -75.9(2) . . . . ?
C1 C2 C27 C26 165.8(2) . . . . ?
C3 C2 C27 C26 42.6(2) . . . . ?
C25 C26 C27 C2 -33.7(3) . . . . ?

_refine_diff_density_max         0.673
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049

