# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_cu_20171024_KMZWS_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2212935'
loop_
_audit_author_name
_audit_author_address
'Xiao-Nian Li'
;Kunming Institute of Botany
China
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-11-28 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         '2(C30 H38 O6), C H4 O'
_chemical_formula_sum            'C61 H80 O13'
_chemical_formula_weight         1021.25

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

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

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

_cell_length_a                   8.6927(9)
_cell_length_b                   29.467(3)
_cell_length_c                   11.3135(12)
_cell_angle_alpha                90
_cell_angle_beta                 112.393(3)
_cell_angle_gamma                90
_cell_volume                     2679.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    9471
_cell_measurement_theta_min      4.23
_cell_measurement_theta_max      72.57

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             1100
_exptl_transmission_factor_min   0.4933
_exptl_transmission_factor_max   0.5863
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.708
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.946
_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      130(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33070
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.999
_diffrn_reflns_theta_max         72.733
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10338
_reflns_number_gt                10282
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_max     0.982
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²+1.1553P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 4885 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         10338
_refine_ls_number_parameters     691
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.039
_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
O8 O 0.8301(5) 0.48131(10) 0.6950(4) 0.0353(8) Uani 1 1 d . . . . .
H8 H 0.8879 0.5032 0.6880 0.053 Uiso 1 1 calc R U . . .
O5 O 0.6638(5) 0.51568(10) 0.3648(4) 0.0343(8) Uani 1 1 d . . . . .
H5 H 0.6079 0.5174 0.4109 0.051 Uiso 1 1 calc R U . . .
O1 O 0.8713(4) 0.69378(11) 0.2079(4) 0.0320(8) Uani 1 1 d . . . . .
O12 O 1.2023(4) 0.30665(10) 0.8326(3) 0.0303(7) Uani 1 1 d . . . . .
O10 O 0.5245(4) 0.34048(12) 0.8900(4) 0.0349(8) Uani 1 1 d . . . . .
H10 H 0.4246 0.3322 0.8563 0.052 Uiso 1 1 calc R U . . .
O3 O 0.1474(4) 0.65102(12) 0.1725(4) 0.0373(8) Uani 1 1 d . . . . .
H3 H 0.0932 0.6661 0.2066 0.056 Uiso 1 1 calc R U . . .
O6 O 0.9750(5) 0.54618(13) 0.5731(4) 0.0430(9) Uani 1 1 d . . . . .
H6 H 1.0614 0.5568 0.5673 0.065 Uiso 1 1 calc R U . . .
O2 O 0.6031(4) 0.73358(10) 0.2234(3) 0.0312(7) Uani 1 1 d . . . . .
H2 H 0.6820 0.7505 0.2259 0.047 Uiso 1 1 calc R U . . .
O11 O 0.9272(4) 0.26347(10) 0.8280(4) 0.0345(8) Uani 1 1 d . . . . .
H11 H 1.0036 0.2497 0.8147 0.052 Uiso 1 1 calc R U . . .
C11 C 1.1927(6) 0.36356(15) 0.9775(5) 0.0279(9) Uani 1 1 d . . . . .
H11A H 1.3023 0.3740 0.9940 0.034 Uiso 1 1 calc R U . . .
O7 O 0.9271(5) 0.45404(12) 0.4791(4) 0.0401(8) Uani 1 1 d . . . . .
H7 H 1.0116 0.4674 0.5302 0.060 Uiso 1 1 calc R U . . .
C55 C 0.7446(6) 0.55921(14) 0.3654(5) 0.0272(9) Uani 1 1 d . . . . .
O9 O 0.5440(5) 0.43854(13) 0.8467(4) 0.0440(9) Uani 1 1 d . . . . .
O4 O 0.2263(5) 0.55494(13) 0.2221(4) 0.0433(9) Uani 1 1 d . . . . .
C59 C 0.8938(5) 0.62325(16) 0.5077(5) 0.0297(10) Uani 1 1 d . . . . .
H59A H 0.9641 0.6258 0.4568 0.036 Uiso 1 1 calc R U . . .
H59B H 0.9633 0.6313 0.5971 0.036 Uiso 1 1 calc R U . . .
C43 C 0.5743(5) 0.70040(14) 0.1256(4) 0.0260(9) Uani 1 1 d . . . . .
C12 C 1.1348(5) 0.32217(14) 0.9029(5) 0.0254(9) Uani 1 1 d . . . . .
C39 C 0.4431(5) 0.61861(14) 0.0727(5) 0.0254(9) Uani 1 1 d . . . . .
C56 C 0.8576(6) 0.55122(16) 0.2914(5) 0.0328(10) Uani 1 1 d . . . . .
H56A H 0.9432 0.5289 0.3369 0.049 Uiso 1 1 calc R U . . .
H56B H 0.9109 0.5798 0.2844 0.049 Uiso 1 1 calc R U . . .
H56C H 0.7910 0.5399 0.2057 0.049 Uiso 1 1 calc R U . . .
C49 C 0.6101(5) 0.59408(15) 0.3034(5) 0.0245(9) Uani 1 1 d . . . . .
C50 C 0.3166(6) 0.58584(15) 0.2223(5) 0.0301(10) Uani 1 1 d . . . . .
C48 C 0.6058(5) 0.63587(14) 0.3488(4) 0.0252(9) Uani 1 1 d . . . . .
C7 C 1.1600(6) 0.42840(15) 1.1038(5) 0.0321(10) Uani 1 1 d . . . . .
C44 C 0.4408(5) 0.66693(14) 0.1324(5) 0.0236(9) Uani 1 1 d . . . . .
H44 H 0.3302 0.6807 0.0815 0.028 Uiso 1 1 calc R U . . .
C40 C 0.7265(7) 0.55301(19) -0.0723(6) 0.0389(11) Uani 1 1 d . . . . .
H40A H 0.7054 0.5231 -0.1135 0.058 Uiso 1 1 calc R U . . .
H40B H 0.8228 0.5512 0.0088 0.058 Uiso 1 1 calc R U . . .
H40C H 0.7491 0.5750 -0.1285 0.058 Uiso 1 1 calc R U . . .
C25 C 0.6934(7) 0.3162(2) 0.4975(6) 0.0413(12) Uani 1 1 d . . . . .
C17 C 0.6339(6) 0.40842(15) 0.8402(4) 0.0286(9) Uani 1 1 d . . . . .
C13 C 0.9971(6) 0.29638(14) 0.9245(5) 0.0272(9) Uani 1 1 d . . . . .
C21 C 0.9124(6) 0.43898(15) 0.6890(5) 0.0279(9) Uani 1 1 d . . . . .
C8 C 1.0955(6) 0.38741(15) 1.0239(5) 0.0283(10) Uani 1 1 d . . . . .
C53 C 0.7494(5) 0.65742(14) 0.4558(5) 0.0274(9) Uani 1 1 d . . . . .
H53 H 0.7904 0.6824 0.4157 0.033 Uiso 1 1 calc R U . . .
C10 C 1.3339(7) 0.44384(18) 1.1276(6) 0.0381(11) Uani 1 1 d . . . . .
H10A H 1.3585 0.4714 1.1800 0.057 Uiso 1 1 calc R U . . .
H10B H 1.3438 0.4502 1.0458 0.057 Uiso 1 1 calc R U . . .
H10C H 1.4128 0.4199 1.1727 0.057 Uiso 1 1 calc R U . . .
C20 C 0.8463(5) 0.40312(14) 0.7552(5) 0.0250(9) Uani 1 1 d . . . . .
C18 C 0.8203(5) 0.41352(13) 0.8772(5) 0.0244(9) Uani 1 1 d . . . . .
H18 H 0.8580 0.4450 0.9079 0.029 Uiso 1 1 calc R U . . .
C16 C 0.5746(6) 0.35983(15) 0.7944(5) 0.0301(10) Uani 1 1 d . . . . .
C33 C 0.2267(6) 0.64224(16) -0.1496(5) 0.0319(10) Uani 1 1 d . . . . .
C4 C 0.8554(6) 0.38525(15) 1.0986(5) 0.0302(9) Uani 1 1 d . . . . .
H4 H 0.7314 0.3827 1.0632 0.036 Uiso 1 1 calc R U . . .
C2 C 0.9206(7) 0.35055(16) 1.2063(5) 0.0322(10) Uani 1 1 d . . . . .
C9 C 0.9115(5) 0.37699(14) 0.9844(5) 0.0265(9) Uani 1 1 d . . . . .
C6 C 1.0648(7) 0.44971(16) 1.1566(5) 0.0363(11) Uani 1 1 d . . . . .
H6A H 1.1079 0.4768 1.2029 0.044 Uiso 1 1 calc R U . . .
C30 C 0.7986(5) 0.36092(15) 0.7082(5) 0.0264(9) Uani 1 1 d . . . . .
C41 C 0.7245(5) 0.63499(15) 0.0709(5) 0.0284(9) Uani 1 1 d . . . . .
H41 H 0.8172 0.6257 0.0518 0.034 Uiso 1 1 calc R U . . .
C47 C 0.4490(5) 0.66156(13) 0.2708(4) 0.0239(9) Uani 1 1 d . . . . .
H47 H 0.4501 0.6921 0.3095 0.029 Uiso 1 1 calc R U . . .
C35 C 0.2720(6) 0.55913(15) -0.0865(5) 0.0334(11) Uani 1 1 d . . . . .
H35A H 0.2490 0.5384 -0.0263 0.040 Uiso 1 1 calc R U . . .
H35B H 0.1803 0.5557 -0.1711 0.040 Uiso 1 1 calc R U . . .
C51 C 0.2961(5) 0.63404(16) 0.2695(5) 0.0290(10) Uani 1 1 d . . . . .
C42 C 0.7361(6) 0.67651(15) 0.1433(5) 0.0277(9) Uani 1 1 d . . . . .
C38 C 0.5855(5) 0.60930(15) 0.0301(5) 0.0259(9) Uani 1 1 d . . . . .
C37 C 0.5741(7) 0.56810(16) -0.0468(5) 0.0327(10) Uani 1 1 d . . . . .
C5 C 0.8974(7) 0.43446(16) 1.1486(5) 0.0356(11) Uani 1 1 d . . . . .
H5A H 0.8119 0.4552 1.0912 0.043 Uiso 1 1 calc R U . . .
H5B H 0.8929 0.4365 1.2346 0.043 Uiso 1 1 calc R U . . .
C54 C 0.8363(6) 0.57434(16) 0.5038(5) 0.0323(10) Uani 1 1 d . . . . .
H54 H 0.7560 0.5730 0.5478 0.039 Uiso 1 1 calc R U . . .
C32 C 0.3042(7) 0.63948(18) -0.2460(5) 0.0382(11) Uani 1 1 d . . . . .
H32A H 0.2725 0.6108 -0.2931 0.057 Uiso 1 1 calc R U . . .
H32B H 0.4256 0.6408 -0.2027 0.057 Uiso 1 1 calc R U . . .
H32C H 0.2657 0.6650 -0.3058 0.057 Uiso 1 1 calc R U . . .
C14 C 0.8555(6) 0.32863(14) 0.9233(5) 0.0257(9) Uani 1 1 d . . . . .
H14 H 0.7985 0.3135 0.9745 0.031 Uiso 1 1 calc R U . . .
C29 C 1.0981(6) 0.44713(15) 0.7584(5) 0.0299(10) Uani 1 1 d . . . . .
H29A H 1.1351 0.4701 0.7124 0.045 Uiso 1 1 calc R U . . .
H29B H 1.1586 0.4188 0.7620 0.045 Uiso 1 1 calc R U . . .
H29C H 1.1204 0.4577 0.8455 0.045 Uiso 1 1 calc R U . . .
C57 C 0.7087(6) 0.6795(2) 0.5626(6) 0.0438(13) Uani 1 1 d . . . . .
C52 C 0.2805(6) 0.63190(19) 0.3974(5) 0.0372(11) Uani 1 1 d . . . . .
H52A H 0.2592 0.6624 0.4223 0.056 Uiso 1 1 calc R U . . .
H52B H 0.3840 0.6201 0.4616 0.056 Uiso 1 1 calc R U . . .
H52C H 0.1880 0.6118 0.3917 0.056 Uiso 1 1 calc R U . . .
C36 C 0.4327(7) 0.54513(15) -0.0973(5) 0.0351(11) Uani 1 1 d . . . . .
H36 H 0.4328 0.5181 -0.1433 0.042 Uiso 1 1 calc R U . . .
C1 C 0.8201(8) 0.31827(18) 1.2177(6) 0.0403(12) Uani 1 1 d . . . . .
H1A H 0.8590 0.2975 1.2871 0.048 Uiso 1 1 calc R U . . .
H1B H 0.7095 0.3160 1.1564 0.048 Uiso 1 1 calc R U . . .
C15 C 0.7244(6) 0.33373(15) 0.7858(5) 0.0279(10) Uani 1 1 d . . . . .
H15 H 0.6884 0.3032 0.7462 0.034 Uiso 1 1 calc R U . . .
C19 C 0.4290(6) 0.3620(2) 0.6653(6) 0.0398(12) Uani 1 1 d . . . . .
H19A H 0.3875 0.3313 0.6382 0.060 Uiso 1 1 calc R U . . .
H19B H 0.4664 0.3756 0.6018 0.060 Uiso 1 1 calc R U . . .
H19C H 0.3398 0.3805 0.6731 0.060 Uiso 1 1 calc R U . . .
C22 C 0.8624(6) 0.42441(16) 0.5487(5) 0.0297(9) Uani 1 1 d . . . . .
H22 H 0.7382 0.4251 0.5071 0.036 Uiso 1 1 calc R U . . .
C34 C 0.2732(5) 0.60854(14) -0.0398(5) 0.0290(10) Uani 1 1 d . . . . .
H34 H 0.1849 0.6106 -0.0036 0.035 Uiso 1 1 calc R U . . .
C60 C 0.7099(11) 0.7251(3) 0.5708(9) 0.083(3) Uani 1 1 d . . . . .
H60A H 0.6966 0.7393 0.6416 0.100 Uiso 1 1 calc R U . . .
H60B H 0.7239 0.7429 0.5057 0.100 Uiso 1 1 calc R U . . .
C3 C 1.0971(7) 0.35451(19) 1.3036(6) 0.0407(12) Uani 1 1 d . . . . .
H3A H 1.1116 0.3839 1.3471 0.061 Uiso 1 1 calc R U . . .
H3B H 1.1751 0.3522 1.2601 0.061 Uiso 1 1 calc R U . . .
H3C H 1.1190 0.3300 1.3665 0.061 Uiso 1 1 calc R U . . .
C46 C 0.4635(5) 0.58205(14) 0.1817(5) 0.0262(9) Uani 1 1 d . . . . .
H46 H 0.4742 0.5506 0.1524 0.031 Uiso 1 1 calc R U . . .
C24 C 0.8360(6) 0.34092(15) 0.5983(5) 0.0292(9) Uani 1 1 d . . . . .
H24 H 0.9228 0.3172 0.6381 0.035 Uiso 1 1 calc R U . . .
C31 C 0.1104(6) 0.67303(17) -0.1576(5) 0.0366(11) Uani 1 1 d . . . . .
H31A H 0.0749 0.6940 -0.2265 0.044 Uiso 1 1 calc R U . . .
H31B H 0.0633 0.6739 -0.0945 0.044 Uiso 1 1 calc R U . . .
C23 C 0.9198(6) 0.37615(15) 0.5409(5) 0.0291(9) Uani 1 1 d . . . . .
H23A H 1.0419 0.3744 0.5871 0.035 Uiso 1 1 calc R U . . .
H23B H 0.8944 0.3684 0.4503 0.035 Uiso 1 1 calc R U . . .
C45 C 0.5153(6) 0.72435(16) -0.0047(5) 0.0325(10) Uani 1 1 d . . . . .
H45A H 0.4137 0.7416 -0.0177 0.049 Uiso 1 1 calc R U . . .
H45B H 0.4924 0.7017 -0.0727 0.049 Uiso 1 1 calc R U . . .
H45C H 0.6023 0.7451 -0.0070 0.049 Uiso 1 1 calc R U . . .
O1S O 0.5118(6) 0.5028(5) 0.5329(7) 0.134(4) Uani 1 1 d . . . . .
H1S H 0.5699 0.4801 0.5671 0.201 Uiso 1 1 calc R U . . .
C28 C 1.0764(7) 0.27215(17) 1.0544(5) 0.0374(11) Uani 1 1 d . . . . .
H28A H 0.9896 0.2567 1.0746 0.056 Uiso 1 1 calc R U . . .
H28B H 1.1324 0.2945 1.1211 0.056 Uiso 1 1 calc R U . . .
H28C H 1.1577 0.2498 1.0502 0.056 Uiso 1 1 calc R U . . .
C26 C 0.5666(8) 0.3417(3) 0.3977(7) 0.0632(19) Uani 1 1 d . . . . .
H26A H 0.4808 0.3262 0.3313 0.076 Uiso 1 1 calc R U . . .
H26B H 0.5694 0.3739 0.3987 0.076 Uiso 1 1 calc R U . . .
C58 C 0.6870(9) 0.6499(4) 0.6631(8) 0.080(3) Uani 1 1 d . . . . .
H58A H 0.7908 0.6336 0.7095 0.120 Uiso 1 1 calc R U . . .
H58B H 0.5974 0.6280 0.6225 0.120 Uiso 1 1 calc R U . . .
H58C H 0.6584 0.6688 0.7231 0.120 Uiso 1 1 calc R U . . .
C27 C 0.6937(13) 0.2699(3) 0.4994(9) 0.081(3) Uani 1 1 d . . . . .
H27A H 0.6049 0.2585 0.4221 0.121 Uiso 1 1 calc R U . . .
H27B H 0.6751 0.2593 0.5750 0.121 Uiso 1 1 calc R U . . .
H27C H 0.8014 0.2587 0.5026 0.121 Uiso 1 1 calc R U . . .
C1S C 0.3583(10) 0.4974(5) 0.5316(10) 0.086(2) Uani 1 1 d . . . . .
H1S1 H 0.2995 0.5266 0.5127 0.129 Uiso 1 1 calc R U . . .
H1S2 H 0.3654 0.4866 0.6154 0.129 Uiso 1 1 calc R U . . .
H1S3 H 0.2976 0.4752 0.4659 0.129 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
O8 C21 1.452(5) . ?
O8 H8 0.8400 . ?
O5 C55 1.461(5) . ?
O5 H5 0.8400 . ?
O1 C42 1.233(6) . ?
O12 C12 1.242(6) . ?
O10 C16 1.429(6) . ?
O10 H10 0.8400 . ?
O3 C51 1.430(6) . ?
O3 H3 0.8400 . ?
O6 C54 1.427(6) . ?
O6 H6 0.8400 . ?
O2 C43 1.425(6) . ?
O2 H2 0.8400 . ?
O11 C13 1.412(6) . ?
O11 H11 0.8400 . ?
C11 C8 1.349(7) . ?
C11 C12 1.460(7) . ?
C11 H11A 0.9500 . ?
O7 C22 1.427(6) . ?
O7 H7 0.8400 . ?
C55 C49 1.513(6) . ?
C55 C54 1.528(7) . ?
C55 C56 1.532(7) . ?
O9 C17 1.204(6) . ?
O4 C50 1.202(6) . ?
C59 C54 1.520(6) . ?
C59 C53 1.540(6) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C43 C42 1.516(6) . ?
C43 C45 1.536(7) . ?
C43 C44 1.547(6) . ?
C12 C13 1.514(6) . ?
C39 C38 1.514(6) . ?
C39 C34 1.567(6) . ?
C39 C44 1.579(6) . ?
C39 C46 1.596(6) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C49 C48 1.340(6) . ?
C49 C46 1.519(6) . ?
C50 C46 1.517(7) . ?
C50 C51 1.551(7) . ?
C48 C53 1.509(6) . ?
C48 C47 1.514(6) . ?
C7 C6 1.346(8) . ?
C7 C8 1.484(7) . ?
C7 C10 1.501(7) . ?
C44 C47 1.549(7) . ?
C44 H44 1.0000 . ?
C40 C37 1.525(7) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C25 C27 1.362(11) . ?
C25 C26 1.452(10) . ?
C25 C24 1.515(7) . ?
C17 C18 1.519(6) . ?
C17 C16 1.543(6) . ?
C13 C28 1.541(7) . ?
C13 C14 1.551(6) . ?
C21 C29 1.521(6) . ?
C21 C20 1.528(6) . ?
C21 C22 1.539(7) . ?
C8 C9 1.519(6) . ?
C53 C57 1.526(7) . ?
C53 H53 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C20 C30 1.354(6) . ?
C20 C18 1.513(7) . ?
C18 C9 1.589(6) . ?
C18 H18 1.0000 . ?
C16 C19 1.526(7) . ?
C16 C15 1.547(6) . ?
C33 C31 1.335(7) . ?
C33 C32 1.487(8) . ?
C33 C34 1.520(7) . ?
C4 C2 1.525(7) . ?
C4 C5 1.549(6) . ?
C4 C9 1.565(7) . ?
C4 H4 1.0000 . ?
C2 C1 1.330(8) . ?
C2 C3 1.514(8) . ?
C9 C14 1.578(6) . ?
C6 C5 1.493(7) . ?
C6 H6A 0.9500 . ?
C30 C15 1.504(7) . ?
C30 C24 1.518(7) . ?
C41 C38 1.350(7) . ?
C41 C42 1.455(7) . ?
C41 H41 0.9500 . ?
C47 C51 1.552(6) . ?
C47 H47 1.0000 . ?
C35 C36 1.506(7) . ?
C35 C34 1.547(6) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C51 C52 1.506(7) . ?
C38 C37 1.474(6) . ?
C37 C36 1.327(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C54 H54 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C14 C15 1.546(7) . ?
C14 H14 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C57 C60 1.347(11) . ?
C57 C58 1.501(11) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C36 H36 0.9500 . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C15 H15 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C22 C23 1.520(6) . ?
C22 H22 1.0000 . ?
C34 H34 1.0000 . ?
C60 H60A 0.9500 . ?
C60 H60B 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C46 H46 1.0000 . ?
C24 C23 1.546(7) . ?
C24 H24 1.0000 . ?
C31 H31A 0.9500 . ?
C31 H31B 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
O1S C1S 1.338(9) . ?
O1S H1S 0.8400 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C26 H26A 0.9500 . ?
C26 H26B 0.9500 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O8 H8 109.5 . . ?
C55 O5 H5 109.5 . . ?
C16 O10 H10 109.5 . . ?
C51 O3 H3 109.5 . . ?
C54 O6 H6 109.5 . . ?
C43 O2 H2 109.5 . . ?
C13 O11 H11 109.5 . . ?
C8 C11 C12 122.1(4) . . ?
C8 C11 H11A 119.0 . . ?
C12 C11 H11A 119.0 . . ?
C22 O7 H7 109.5 . . ?
O5 C55 C49 108.0(4) . . ?
O5 C55 C54 108.9(4) . . ?
C49 C55 C54 106.6(4) . . ?
O5 C55 C56 105.6(4) . . ?
C49 C55 C56 113.2(4) . . ?
C54 C55 C56 114.3(4) . . ?
C54 C59 C53 113.4(4) . . ?
C54 C59 H59A 108.9 . . ?
C53 C59 H59A 108.9 . . ?
C54 C59 H59B 108.9 . . ?
C53 C59 H59B 108.9 . . ?
H59A C59 H59B 107.7 . . ?
O2 C43 C42 109.7(4) . . ?
O2 C43 C45 109.0(4) . . ?
C42 C43 C45 107.1(4) . . ?
O2 C43 C44 108.2(4) . . ?
C42 C43 C44 111.9(3) . . ?
C45 C43 C44 111.0(4) . . ?
O12 C12 C11 122.4(4) . . ?
O12 C12 C13 120.9(4) . . ?
C11 C12 C13 116.5(4) . . ?
C38 C39 C34 109.8(4) . . ?
C38 C39 C44 116.4(4) . . ?
C34 C39 C44 110.9(3) . . ?
C38 C39 C46 105.1(3) . . ?
C34 C39 C46 107.0(3) . . ?
C44 C39 C46 107.1(4) . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C48 C49 C55 125.1(4) . . ?
C48 C49 C46 115.2(4) . . ?
C55 C49 C46 119.7(4) . . ?
O4 C50 C46 124.6(4) . . ?
O4 C50 C51 122.3(4) . . ?
C46 C50 C51 113.1(4) . . ?
C49 C48 C53 124.0(4) . . ?
C49 C48 C47 112.7(4) . . ?
C53 C48 C47 122.9(4) . . ?
C6 C7 C8 119.8(4) . . ?
C6 C7 C10 121.7(5) . . ?
C8 C7 C10 118.5(4) . . ?
C43 C44 C47 111.6(4) . . ?
C43 C44 C39 115.0(3) . . ?
C47 C44 C39 109.7(3) . . ?
C43 C44 H44 106.7 . . ?
C47 C44 H44 106.7 . . ?
C39 C44 H44 106.7 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C27 C25 C26 121.8(7) . . ?
C27 C25 C24 118.3(6) . . ?
C26 C25 C24 119.8(6) . . ?
O9 C17 C18 124.0(4) . . ?
O9 C17 C16 124.3(4) . . ?
C18 C17 C16 111.7(4) . . ?
O11 C13 C12 110.7(4) . . ?
O11 C13 C28 108.9(4) . . ?
C12 C13 C28 107.0(4) . . ?
O11 C13 C14 107.9(4) . . ?
C12 C13 C14 111.4(3) . . ?
C28 C13 C14 110.9(4) . . ?
O8 C21 C29 106.6(4) . . ?
O8 C21 C20 106.7(3) . . ?
C29 C21 C20 112.3(4) . . ?
O8 C21 C22 109.7(4) . . ?
C29 C21 C22 113.8(4) . . ?
C20 C21 C22 107.5(4) . . ?
C11 C8 C7 120.9(4) . . ?
C11 C8 C9 121.7(4) . . ?
C7 C8 C9 117.1(4) . . ?
C48 C53 C57 116.4(4) . . ?
C48 C53 C59 109.6(4) . . ?
C57 C53 C59 112.2(4) . . ?
C48 C53 H53 106.0 . . ?
C57 C53 H53 106.0 . . ?
C59 C53 H53 106.0 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C30 C20 C18 114.5(4) . . ?
C30 C20 C21 124.0(4) . . ?
C18 C20 C21 121.4(4) . . ?
C20 C18 C17 104.1(4) . . ?
C20 C18 C9 110.8(3) . . ?
C17 C18 C9 108.2(4) . . ?
C20 C18 H18 111.2 . . ?
C17 C18 H18 111.2 . . ?
C9 C18 H18 111.2 . . ?
O10 C16 C19 111.1(4) . . ?
O10 C16 C17 106.0(4) . . ?
C19 C16 C17 109.4(4) . . ?
O10 C16 C15 110.8(4) . . ?
C19 C16 C15 111.8(4) . . ?
C17 C16 C15 107.5(3) . . ?
C31 C33 C32 122.0(5) . . ?
C31 C33 C34 117.3(5) . . ?
C32 C33 C34 120.7(4) . . ?
C2 C4 C5 111.8(4) . . ?
C2 C4 C9 114.7(4) . . ?
C5 C4 C9 110.1(4) . . ?
C2 C4 H4 106.6 . . ?
C5 C4 H4 106.6 . . ?
C9 C4 H4 106.6 . . ?
C1 C2 C3 120.4(5) . . ?
C1 C2 C4 119.9(5) . . ?
C3 C2 C4 119.6(4) . . ?
C8 C9 C4 110.5(4) . . ?
C8 C9 C14 115.2(4) . . ?
C4 C9 C14 111.2(4) . . ?
C8 C9 C18 104.5(3) . . ?
C4 C9 C18 107.7(3) . . ?
C14 C9 C18 107.3(4) . . ?
C7 C6 C5 125.6(5) . . ?
C7 C6 H6A 117.2 . . ?
C5 C6 H6A 117.2 . . ?
C20 C30 C15 113.3(4) . . ?
C20 C30 C24 123.3(4) . . ?
C15 C30 C24 123.0(4) . . ?
C38 C41 C42 121.7(4) . . ?
C38 C41 H41 119.2 . . ?
C42 C41 H41 119.2 . . ?
C48 C47 C44 109.0(3) . . ?
C48 C47 C51 108.8(3) . . ?
C44 C47 C51 109.5(4) . . ?
C48 C47 H47 109.9 . . ?
C44 C47 H47 109.9 . . ?
C51 C47 H47 109.9 . . ?
C36 C35 C34 113.6(4) . . ?
C36 C35 H35A 108.9 . . ?
C34 C35 H35A 108.9 . . ?
C36 C35 H35B 108.9 . . ?
C34 C35 H35B 108.9 . . ?
H35A C35 H35B 107.7 . . ?
O3 C51 C52 111.5(4) . . ?
O3 C51 C47 110.2(4) . . ?
C52 C51 C47 113.8(4) . . ?
O3 C51 C50 104.2(4) . . ?
C52 C51 C50 110.9(4) . . ?
C47 C51 C50 105.8(3) . . ?
O1 C42 C41 121.8(4) . . ?
O1 C42 C43 120.9(4) . . ?
C41 C42 C43 117.0(4) . . ?
C41 C38 C37 120.9(4) . . ?
C41 C38 C39 121.6(4) . . ?
C37 C38 C39 117.2(4) . . ?
C36 C37 C38 121.1(5) . . ?
C36 C37 C40 119.9(4) . . ?
C38 C37 C40 118.9(5) . . ?
C6 C5 C4 113.1(4) . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
O6 C54 C59 109.6(4) . . ?
O6 C54 C55 113.3(4) . . ?
C59 C54 C55 110.1(4) . . ?
O6 C54 H54 107.9 . . ?
C59 C54 H54 107.9 . . ?
C55 C54 H54 107.9 . . ?
C33 C32 H32A 109.5 . . ?
C33 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C33 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C15 C14 C13 110.3(4) . . ?
C15 C14 C9 109.8(4) . . ?
C13 C14 C9 116.0(4) . . ?
C15 C14 H14 106.8 . . ?
C13 C14 H14 106.8 . . ?
C9 C14 H14 106.8 . . ?
C21 C29 H29A 109.5 . . ?
C21 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C21 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C60 C57 C58 121.8(7) . . ?
C60 C57 C53 118.8(7) . . ?
C58 C57 C53 119.1(6) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C37 C36 C35 124.1(4) . . ?
C37 C36 H36 117.9 . . ?
C35 C36 H36 117.9 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C30 C15 C16 109.3(4) . . ?
C30 C15 C14 108.9(4) . . ?
C16 C15 C14 107.5(4) . . ?
C30 C15 H15 110.4 . . ?
C16 C15 H15 110.4 . . ?
C14 C15 H15 110.4 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O7 C22 C23 109.5(4) . . ?
O7 C22 C21 112.5(4) . . ?
C23 C22 C21 110.5(4) . . ?
O7 C22 H22 108.1 . . ?
C23 C22 H22 108.1 . . ?
C21 C22 H22 108.1 . . ?
C33 C34 C35 111.8(4) . . ?
C33 C34 C39 114.5(4) . . ?
C35 C34 C39 109.7(4) . . ?
C33 C34 H34 106.8 . . ?
C35 C34 H34 106.8 . . ?
C39 C34 H34 106.8 . . ?
C57 C60 H60A 120.0 . . ?
C57 C60 H60B 120.0 . . ?
H60A C60 H60B 120.0 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C50 C46 C49 102.8(4) . . ?
C50 C46 C39 109.0(4) . . ?
C49 C46 C39 110.5(3) . . ?
C50 C46 H46 111.4 . . ?
C49 C46 H46 111.4 . . ?
C39 C46 H46 111.4 . . ?
C30 C24 C25 115.7(4) . . ?
C30 C24 C23 111.4(4) . . ?
C25 C24 C23 112.9(4) . . ?
C30 C24 H24 105.2 . . ?
C25 C24 H24 105.2 . . ?
C23 C24 H24 105.2 . . ?
C33 C31 H31A 120.0 . . ?
C33 C31 H31B 120.0 . . ?
H31A C31 H31B 120.0 . . ?
C22 C23 C24 112.7(4) . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C1S O1S H1S 109.5 . . ?
C13 C28 H28A 109.5 . . ?
C13 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C13 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C26 H26A 120.0 . . ?
C25 C26 H26B 120.0 . . ?
H26A C26 H26B 120.0 . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C57 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O1S C1S H1S1 109.5 . . ?
O1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
O1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 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
C8 C11 C12 O12 160.6(5) . . . . ?
C8 C11 C12 C13 -24.8(7) . . . . ?
O5 C55 C49 C48 134.7(5) . . . . ?
C54 C55 C49 C48 17.8(6) . . . . ?
C56 C55 C49 C48 -108.8(5) . . . . ?
O5 C55 C49 C46 -43.6(6) . . . . ?
C54 C55 C49 C46 -160.5(4) . . . . ?
C56 C55 C49 C46 72.9(5) . . . . ?
C55 C49 C48 C53 11.3(7) . . . . ?
C46 C49 C48 C53 -170.3(4) . . . . ?
C55 C49 C48 C47 -175.7(4) . . . . ?
C46 C49 C48 C47 2.6(6) . . . . ?
O2 C43 C44 C47 -31.0(5) . . . . ?
C42 C43 C44 C47 89.9(4) . . . . ?
C45 C43 C44 C47 -150.6(4) . . . . ?
O2 C43 C44 C39 -156.8(4) . . . . ?
C42 C43 C44 C39 -35.9(5) . . . . ?
C45 C43 C44 C39 83.6(5) . . . . ?
C38 C39 C44 C43 6.5(6) . . . . ?
C34 C39 C44 C43 -119.9(4) . . . . ?
C46 C39 C44 C43 123.7(4) . . . . ?
C38 C39 C44 C47 -120.3(4) . . . . ?
C34 C39 C44 C47 113.3(4) . . . . ?
C46 C39 C44 C47 -3.1(4) . . . . ?
O12 C12 C13 O11 -18.6(6) . . . . ?
C11 C12 C13 O11 166.8(4) . . . . ?
O12 C12 C13 C28 99.9(5) . . . . ?
C11 C12 C13 C28 -74.7(5) . . . . ?
O12 C12 C13 C14 -138.7(4) . . . . ?
C11 C12 C13 C14 46.7(5) . . . . ?
C12 C11 C8 C7 177.6(4) . . . . ?
C12 C11 C8 C9 -9.7(7) . . . . ?
C6 C7 C8 C11 -175.2(5) . . . . ?
C10 C7 C8 C11 2.4(7) . . . . ?
C6 C7 C8 C9 11.8(7) . . . . ?
C10 C7 C8 C9 -170.7(4) . . . . ?
C49 C48 C53 C57 -131.8(5) . . . . ?
C47 C48 C53 C57 56.0(6) . . . . ?
C49 C48 C53 C59 -3.2(6) . . . . ?
C47 C48 C53 C59 -175.4(4) . . . . ?
C54 C59 C53 C48 -33.9(6) . . . . ?
C54 C59 C53 C57 97.0(5) . . . . ?
O8 C21 C20 C30 135.2(4) . . . . ?
C29 C21 C20 C30 -108.4(5) . . . . ?
C22 C21 C20 C30 17.6(6) . . . . ?
O8 C21 C20 C18 -41.3(5) . . . . ?
C29 C21 C20 C18 75.1(5) . . . . ?
C22 C21 C20 C18 -158.9(4) . . . . ?
C30 C20 C18 C17 -60.5(5) . . . . ?
C21 C20 C18 C17 116.4(4) . . . . ?
C30 C20 C18 C9 55.6(5) . . . . ?
C21 C20 C18 C9 -127.6(4) . . . . ?
O9 C17 C18 C20 -119.5(5) . . . . ?
C16 C17 C18 C20 61.0(5) . . . . ?
O9 C17 C18 C9 122.7(5) . . . . ?
C16 C17 C18 C9 -56.9(5) . . . . ?
O9 C17 C16 O10 -67.9(6) . . . . ?
C18 C17 C16 O10 111.7(4) . . . . ?
O9 C17 C16 C19 52.0(7) . . . . ?
C18 C17 C16 C19 -128.5(4) . . . . ?
O9 C17 C16 C15 173.6(5) . . . . ?
C18 C17 C16 C15 -6.9(6) . . . . ?
C5 C4 C2 C1 130.3(5) . . . . ?
C9 C4 C2 C1 -103.4(6) . . . . ?
C5 C4 C2 C3 -46.7(6) . . . . ?
C9 C4 C2 C3 79.6(6) . . . . ?
C11 C8 C9 C4 145.5(4) . . . . ?
C7 C8 C9 C4 -41.6(5) . . . . ?
C11 C8 C9 C14 18.5(6) . . . . ?
C7 C8 C9 C14 -168.6(4) . . . . ?
C11 C8 C9 C18 -99.0(5) . . . . ?
C7 C8 C9 C18 74.0(5) . . . . ?
C2 C4 C9 C8 -71.2(5) . . . . ?
C5 C4 C9 C8 56.0(5) . . . . ?
C2 C4 C9 C14 58.1(5) . . . . ?
C5 C4 C9 C14 -174.8(4) . . . . ?
C2 C4 C9 C18 175.3(4) . . . . ?
C5 C4 C9 C18 -57.6(5) . . . . ?
C20 C18 C9 C8 71.6(4) . . . . ?
C17 C18 C9 C8 -174.9(4) . . . . ?
C20 C18 C9 C4 -170.9(4) . . . . ?
C17 C18 C9 C4 -57.4(4) . . . . ?
C20 C18 C9 C14 -51.2(4) . . . . ?
C17 C18 C9 C14 62.3(4) . . . . ?
C8 C7 C6 C5 3.5(9) . . . . ?
C10 C7 C6 C5 -173.9(5) . . . . ?
C18 C20 C30 C15 1.8(5) . . . . ?
C21 C20 C30 C15 -174.9(4) . . . . ?
C18 C20 C30 C24 -170.9(4) . . . . ?
C21 C20 C30 C24 12.4(7) . . . . ?
C49 C48 C47 C44 -61.0(5) . . . . ?
C53 C48 C47 C44 112.0(5) . . . . ?
C49 C48 C47 C51 58.3(5) . . . . ?
C53 C48 C47 C51 -128.7(4) . . . . ?
C43 C44 C47 C48 -70.2(4) . . . . ?
C39 C44 C47 C48 58.4(4) . . . . ?
C43 C44 C47 C51 170.9(3) . . . . ?
C39 C44 C47 C51 -60.5(4) . . . . ?
C48 C47 C51 O3 -165.6(4) . . . . ?
C44 C47 C51 O3 -46.7(5) . . . . ?
C48 C47 C51 C52 68.3(5) . . . . ?
C44 C47 C51 C52 -172.7(4) . . . . ?
C48 C47 C51 C50 -53.6(5) . . . . ?
C44 C47 C51 C50 65.4(4) . . . . ?
O4 C50 C51 O3 -71.0(6) . . . . ?
C46 C50 C51 O3 110.8(4) . . . . ?
O4 C50 C51 C52 49.0(6) . . . . ?
C46 C50 C51 C52 -129.2(4) . . . . ?
O4 C50 C51 C47 172.8(5) . . . . ?
C46 C50 C51 C47 -5.4(5) . . . . ?
C38 C41 C42 O1 161.2(5) . . . . ?
C38 C41 C42 C43 -24.8(7) . . . . ?
O2 C43 C42 O1 -19.5(6) . . . . ?
C45 C43 C42 O1 98.6(5) . . . . ?
C44 C43 C42 O1 -139.6(5) . . . . ?
O2 C43 C42 C41 166.4(4) . . . . ?
C45 C43 C42 C41 -75.4(5) . . . . ?
C44 C43 C42 C41 46.4(6) . . . . ?
C42 C41 C38 C37 178.0(4) . . . . ?
C42 C41 C38 C39 -8.6(7) . . . . ?
C34 C39 C38 C41 144.2(4) . . . . ?
C44 C39 C38 C41 17.2(6) . . . . ?
C46 C39 C38 C41 -101.0(5) . . . . ?
C34 C39 C38 C37 -42.1(5) . . . . ?
C44 C39 C38 C37 -169.1(4) . . . . ?
C46 C39 C38 C37 72.6(5) . . . . ?
C41 C38 C37 C36 -173.5(5) . . . . ?
C39 C38 C37 C36 12.8(7) . . . . ?
C41 C38 C37 C40 4.1(7) . . . . ?
C39 C38 C37 C40 -169.6(4) . . . . ?
C7 C6 C5 C4 13.0(8) . . . . ?
C2 C4 C5 C6 86.7(6) . . . . ?
C9 C4 C5 C6 -42.1(6) . . . . ?
C53 C59 C54 O6 -170.0(4) . . . . ?
C53 C59 C54 C55 64.8(6) . . . . ?
O5 C55 C54 O6 67.6(5) . . . . ?
C49 C55 C54 O6 -176.1(4) . . . . ?
C56 C55 C54 O6 -50.2(6) . . . . ?
O5 C55 C54 C59 -169.3(4) . . . . ?
C49 C55 C54 C59 -53.0(5) . . . . ?
C56 C55 C54 C59 72.9(5) . . . . ?
O11 C13 C14 C15 -32.6(5) . . . . ?
C12 C13 C14 C15 89.2(5) . . . . ?
C28 C13 C14 C15 -151.7(4) . . . . ?
O11 C13 C14 C9 -158.2(4) . . . . ?
C12 C13 C14 C9 -36.4(6) . . . . ?
C28 C13 C14 C9 82.7(5) . . . . ?
C8 C9 C14 C15 -119.7(4) . . . . ?
C4 C9 C14 C15 113.6(4) . . . . ?
C18 C9 C14 C15 -3.8(5) . . . . ?
C8 C9 C14 C13 6.1(6) . . . . ?
C4 C9 C14 C13 -120.5(4) . . . . ?
C18 C9 C14 C13 122.0(4) . . . . ?
C48 C53 C57 C60 -108.1(6) . . . . ?
C59 C53 C57 C60 124.6(6) . . . . ?
C48 C53 C57 C58 78.4(6) . . . . ?
C59 C53 C57 C58 -48.9(6) . . . . ?
C38 C37 C36 C35 2.4(9) . . . . ?
C40 C37 C36 C35 -175.2(5) . . . . ?
C34 C35 C36 C37 14.1(8) . . . . ?
C20 C30 C15 C16 57.0(5) . . . . ?
C24 C30 C15 C16 -130.3(4) . . . . ?
C20 C30 C15 C14 -60.2(5) . . . . ?
C24 C30 C15 C14 112.5(5) . . . . ?
O10 C16 C15 C30 -166.9(4) . . . . ?
C19 C16 C15 C30 68.6(5) . . . . ?
C17 C16 C15 C30 -51.5(5) . . . . ?
O10 C16 C15 C14 -48.9(5) . . . . ?
C19 C16 C15 C14 -173.4(4) . . . . ?
C17 C16 C15 C14 66.5(5) . . . . ?
C13 C14 C15 C30 -70.5(4) . . . . ?
C9 C14 C15 C30 58.5(4) . . . . ?
C13 C14 C15 C16 171.2(3) . . . . ?
C9 C14 C15 C16 -59.8(4) . . . . ?
O8 C21 C22 O7 68.1(5) . . . . ?
C29 C21 C22 O7 -51.2(5) . . . . ?
C20 C21 C22 O7 -176.2(4) . . . . ?
O8 C21 C22 C23 -169.2(4) . . . . ?
C29 C21 C22 C23 71.6(5) . . . . ?
C20 C21 C22 C23 -53.5(5) . . . . ?
C31 C33 C34 C35 130.8(5) . . . . ?
C32 C33 C34 C35 -47.0(6) . . . . ?
C31 C33 C34 C39 -103.7(5) . . . . ?
C32 C33 C34 C39 78.5(5) . . . . ?
C36 C35 C34 C33 85.3(5) . . . . ?
C36 C35 C34 C39 -42.8(6) . . . . ?
C38 C39 C34 C33 -70.4(5) . . . . ?
C44 C39 C34 C33 59.6(5) . . . . ?
C46 C39 C34 C33 176.1(4) . . . . ?
C38 C39 C34 C35 56.2(5) . . . . ?
C44 C39 C34 C35 -173.8(4) . . . . ?
C46 C39 C34 C35 -57.4(5) . . . . ?
O4 C50 C46 C49 -117.9(5) . . . . ?
C51 C50 C46 C49 60.3(5) . . . . ?
O4 C50 C46 C39 124.8(5) . . . . ?
C51 C50 C46 C39 -57.0(5) . . . . ?
C48 C49 C46 C50 -61.0(5) . . . . ?
C55 C49 C46 C50 117.5(4) . . . . ?
C48 C49 C46 C39 55.2(5) . . . . ?
C55 C49 C46 C39 -126.3(4) . . . . ?
C38 C39 C46 C50 -174.9(4) . . . . ?
C34 C39 C46 C50 -58.1(4) . . . . ?
C44 C39 C46 C50 60.8(4) . . . . ?
C38 C39 C46 C49 72.9(4) . . . . ?
C34 C39 C46 C49 -170.4(4) . . . . ?
C44 C39 C46 C49 -51.5(4) . . . . ?
C20 C30 C24 C25 -135.9(5) . . . . ?
C15 C30 C24 C25 52.1(6) . . . . ?
C20 C30 C24 C23 -5.2(6) . . . . ?
C15 C30 C24 C23 -177.1(4) . . . . ?
C27 C25 C24 C30 -102.3(7) . . . . ?
C26 C25 C24 C30 81.4(6) . . . . ?
C27 C25 C24 C23 127.6(6) . . . . ?
C26 C25 C24 C23 -48.6(7) . . . . ?
O7 C22 C23 C24 -172.3(4) . . . . ?
C21 C22 C23 C24 63.3(5) . . . . ?
C30 C24 C23 C22 -31.9(5) . . . . ?
C25 C24 C23 C22 100.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1S H1S O8 0.84 2.17 2.749(7) 125.8 .
O7 H7 O6 0.84 2.42 2.888(5) 116.2 .
O11 H11 O1 0.84 2.04 2.827(5) 155.1 2_746
O2 H2 O12 0.84 2.17 2.953(5) 155.7 2_756
O3 H3 O1 0.84 2.10 2.871(5) 152.3 1_455
O10 H10 O12 0.84 1.99 2.806(5) 162.1 1_455
O5 H5 O1S 0.84 1.91 2.725(7) 161.6 .
O8 H8 O6 0.84 2.15 2.909(6) 150.5 .
O1S H1S O8 0.84 2.17 2.749(7) 125.8 .
O11 H11 O1 0.84 2.04 2.827(5) 155.1 2_746
O2 H2 O12 0.84 2.17 2.953(5) 155.7 2_756
O3 H3 O1 0.84 2.10 2.871(5) 152.3 1_455
O10 H10 O12 0.84 1.99 2.806(5) 162.1 1_455
O5 H5 O1S 0.84 1.91 2.725(7) 161.6 .
O8 H8 O6 0.84 2.15 2.909(6) 150.5 .
O8 H8 O6 0.84 2.15 2.909(6) 150.5 .
O5 H5 O1S 0.84 1.91 2.725(7) 161.6 .
O10 H10 O12 0.84 1.99 2.806(5) 162.1 1_455
O3 H3 O1 0.84 2.10 2.871(5) 152.3 1_455
O2 H2 O12 0.84 2.17 2.953(5) 155.7 2_756
O11 H11 O1 0.84 2.04 2.827(5) 155.1 2_746
O1S H1S O8 0.84 2.17 2.749(7) 125.8 .

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.044

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_she149_0m
_database_code_depnum_ccdc_archive 'CCDC 2212936'
loop_
_audit_author_name
_audit_author_address
'Xiao-Nian Li'
;Kunming Institute of Botany
China
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-11-28 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         'C30 H34 O4'
_chemical_formula_sum            'C30 H34 O4'
_chemical_formula_weight         458.57

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                   8.7346(3)
_cell_length_b                   9.9202(3)
_cell_length_c                   28.6562(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2483.03(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      4.72
_cell_measurement_theta_max      68.94

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   0.3368
_exptl_transmission_factor_max   0.5853
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.560
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.634
_shelx_estimated_absorpt_T_min   0.599
_shelx_estimated_absorpt_T_max   0.957
_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      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12892
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         4.717
_diffrn_reflns_theta_max         69.183
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             4364
_reflns_number_gt                4314
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_max     0.916
_reflns_Friedel_fraction_full    0.944

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1004P)²+0.8073P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 1779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4364
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9799(2) 0.4708(2) 0.81520(7) 0.0208(5) Uani 1 1 d . . . . .
O2 O 0.7293(2) 0.3449(2) 0.78789(6) 0.0177(5) Uani 1 1 d . . . . .
H2 H 0.8053 0.3770 0.7738 0.027 Uiso 1 1 calc R U . . .
O3 O 0.2932(2) 0.7079(2) 0.90567(7) 0.0261(5) Uani 1 1 d . . . . .
O4 O 0.2742(2) 0.4620(2) 0.84909(7) 0.0204(5) Uani 1 1 d . . . . .
H4 H 0.1839 0.4733 0.8398 0.031 Uiso 1 1 calc R U . . .
C1 C 0.6753(4) 0.5651(3) 0.99981(10) 0.0193(6) Uani 1 1 d . . . . .
H1 H 0.6924 0.5962 1.0307 0.023 Uiso 1 1 calc R U . . .
C2 C 0.7953(3) 0.5644(3) 0.97037(9) 0.0153(6) Uani 1 1 d . . . . .
C3 C 0.7769(3) 0.5186(3) 0.92191(9) 0.0132(6) Uani 1 1 d . . . . .
C4 C 0.6137(3) 0.5044(3) 0.90386(9) 0.0117(5) Uani 1 1 d . . . . .
C5 C 0.5615(3) 0.6574(3) 0.89638(9) 0.0130(5) Uani 1 1 d . . . . .
H5 H 0.5782 0.7118 0.9253 0.016 Uiso 1 1 calc R U . . .
C6 C 0.6475(3) 0.7168(3) 0.85553(9) 0.0145(6) Uani 1 1 d . . . . .
C7 C 0.6250(3) 0.6497(3) 0.81333(9) 0.0143(6) Uani 1 1 d . . . . .
C8 C 0.7017(3) 0.6901(3) 0.77278(10) 0.0183(6) Uani 1 1 d . . . . .
C9 C 0.6920(4) 0.6195(3) 0.72688(10) 0.0249(7) Uani 1 1 d . . . . .
C10 C 0.5495(4) 0.5876(4) 0.70635(10) 0.0260(7) Uani 1 1 d . . . . .
H10A H 0.5460 0.5466 0.6764 0.031 Uiso 1 1 calc R U . . .
H10B H 0.4571 0.6071 0.7225 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4363(3) 0.2012(3) 0.93032(10) 0.0208(6) Uani 1 1 d . . . . .
H11A H 0.4483 0.1076 0.9363 0.025 Uiso 1 1 calc R U . . .
H11B H 0.3556 0.2318 0.9108 0.025 Uiso 1 1 calc R U . . .
C12 C 0.5329(3) 0.2899(3) 0.94949(9) 0.0166(6) Uani 1 1 d . . . . .
C13 C 0.6618(4) 0.2448(3) 0.98063(11) 0.0223(6) Uani 1 1 d . . . . .
H13A H 0.6718 0.1465 0.9789 0.033 Uiso 1 1 calc R U . . .
H13B H 0.6400 0.2716 1.0129 0.033 Uiso 1 1 calc R U . . .
H13C H 0.7575 0.2869 0.9704 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5071(3) 0.4405(3) 0.94166(9) 0.0152(6) Uani 1 1 d . . . . .
H14 H 0.3998 0.4505 0.9300 0.018 Uiso 1 1 calc R U . . .
C15 C 0.8980(3) 0.5085(3) 0.89295(9) 0.0153(6) Uani 1 1 d . . . . .
H15 H 0.9963 0.5355 0.9037 0.018 Uiso 1 1 calc R U . . .
C16 C 0.8816(3) 0.4574(3) 0.84583(9) 0.0145(6) Uani 1 1 d . . . . .
C17 C 0.7441(3) 0.3694(3) 0.83615(9) 0.0135(6) Uani 1 1 d . . . . .
C18 C 0.7793(3) 0.2324(3) 0.85966(10) 0.0182(6) Uani 1 1 d . . . . .
H18A H 0.8739 0.1951 0.8466 0.027 Uiso 1 1 calc R U . . .
H18B H 0.6946 0.1698 0.8539 0.027 Uiso 1 1 calc R U . . .
H18C H 0.7918 0.2456 0.8933 0.027 Uiso 1 1 calc R U . . .
C19 C 0.5945(3) 0.4321(3) 0.85573(9) 0.0120(5) Uani 1 1 d . . . . .
H19 H 0.5207 0.3563 0.8606 0.014 Uiso 1 1 calc R U . . .
C20 C 0.5211(3) 0.5284(3) 0.81914(9) 0.0140(6) Uani 1 1 d . . . . .
H20 H 0.5082 0.4809 0.7886 0.017 Uiso 1 1 calc R U . . .
C21 C 0.7993(4) 0.8021(3) 0.77694(11) 0.0240(7) Uani 1 1 d . . . . .
H21 H 0.8524 0.8332 0.7501 0.029 Uiso 1 1 calc R U . . .
C22 C 0.8204(3) 0.8679(3) 0.81862(11) 0.0232(7) Uani 1 1 d . . . . .
H22 H 0.8877 0.9431 0.8197 0.028 Uiso 1 1 calc R U . . .
C23 C 0.7467(3) 0.8280(3) 0.85919(10) 0.0180(6) Uani 1 1 d . . . . .
C24 C 0.3929(3) 0.6554(3) 0.88284(9) 0.0159(6) Uani 1 1 d . . . . .
C25 C 0.3639(3) 0.5777(3) 0.83754(9) 0.0160(6) Uani 1 1 d . . . . .
C26 C 0.2802(3) 0.6675(3) 0.80279(10) 0.0211(6) Uani 1 1 d . . . . .
H26A H 0.1878 0.7043 0.8174 0.032 Uiso 1 1 calc R U . . .
H26B H 0.2515 0.6143 0.7753 0.032 Uiso 1 1 calc R U . . .
H26C H 0.3474 0.7416 0.7933 0.032 Uiso 1 1 calc R U . . .
C27 C 0.7754(4) 0.8983(3) 0.90483(11) 0.0249(7) Uani 1 1 d . . . . .
H27A H 0.6829 0.9471 0.9143 0.037 Uiso 1 1 calc R U . . .
H27B H 0.8601 0.9622 0.9012 0.037 Uiso 1 1 calc R U . . .
H27C H 0.8019 0.8316 0.9287 0.037 Uiso 1 1 calc R U . . .
C28 C 0.8315(4) 0.5915(4) 0.70365(14) 0.0360(9) Uani 1 1 d . . . . .
H28A H 0.8770 0.6760 0.6926 0.054 Uiso 1 1 calc R U . . .
H28B H 0.8118 0.5321 0.6770 0.054 Uiso 1 1 calc R U . . .
H28C H 0.9023 0.5471 0.7253 0.054 Uiso 1 1 calc R U . . .
C29 C 0.5167(3) 0.5205(3) 0.98740(9) 0.0198(6) Uani 1 1 d . . . . .
H29A H 0.4502 0.6010 0.9848 0.024 Uiso 1 1 calc R U . . .
H29B H 0.4762 0.4639 1.0131 0.024 Uiso 1 1 calc R U . . .
C30 C 0.9521(4) 0.6061(3) 0.98647(10) 0.0226(7) Uani 1 1 d . . . . .
H30A H 0.9460 0.6406 1.0185 0.034 Uiso 1 1 calc R U . . .
H30B H 0.9917 0.6767 0.9658 0.034 Uiso 1 1 calc R U . . .
H30C H 1.0209 0.5281 0.9856 0.034 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 C16 1.235(3) . ?
O2 C17 1.410(3) . ?
O2 H2 0.8400 . ?
O3 C24 1.208(4) . ?
O4 C25 1.429(4) . ?
O4 H4 0.8400 . ?
C1 C2 1.346(4) . ?
C1 C29 1.497(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.470(3) . ?
C2 C30 1.504(4) . ?
C3 C15 1.348(4) . ?
C3 C4 1.523(4) . ?
C4 C14 1.563(4) . ?
C4 C19 1.564(4) . ?
C4 C5 1.600(4) . ?
C5 C6 1.511(4) . ?
C5 C24 1.522(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.395(4) . ?
C6 C23 1.406(4) . ?
C7 C8 1.400(4) . ?
C7 C20 1.515(4) . ?
C8 C21 1.405(5) . ?
C8 C9 1.493(4) . ?
C9 C10 1.413(5) . ?
C9 C28 1.416(4) . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C11 C12 1.337(4) . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
C12 C13 1.505(4) . ?
C12 C14 1.527(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C29 1.535(4) . ?
C14 H14 1.0000 . ?
C15 C16 1.449(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.511(4) . ?
C17 C18 1.548(4) . ?
C17 C19 1.552(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.557(4) . ?
C19 H19 1.0000 . ?
C20 C25 1.550(4) . ?
C20 H20 1.0000 . ?
C21 C22 1.374(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(4) . ?
C22 H22 0.9500 . ?
C23 C27 1.504(4) . ?
C24 C25 1.531(4) . ?
C25 C26 1.523(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O2 H2 109.5 . . ?
C25 O4 H4 109.5 . . ?
C2 C1 C29 124.8(2) . . ?
C2 C1 H1 117.6 . . ?
C29 C1 H1 117.6 . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 C30 121.1(2) . . ?
C3 C2 C30 118.3(2) . . ?
C15 C3 C2 121.3(3) . . ?
C15 C3 C4 121.2(2) . . ?
C2 C3 C4 116.8(2) . . ?
C3 C4 C14 111.1(2) . . ?
C3 C4 C19 116.3(2) . . ?
C14 C4 C19 111.2(2) . . ?
C3 C4 C5 103.0(2) . . ?
C14 C4 C5 107.9(2) . . ?
C19 C4 C5 106.6(2) . . ?
C6 C5 C24 106.8(2) . . ?
C6 C5 C4 109.4(2) . . ?
C24 C5 C4 107.3(2) . . ?
C6 C5 H5 111.1 . . ?
C24 C5 H5 111.1 . . ?
C4 C5 H5 111.1 . . ?
C7 C6 C23 121.8(3) . . ?
C7 C6 C5 114.5(2) . . ?
C23 C6 C5 123.7(2) . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 C20 111.6(2) . . ?
C8 C7 C20 127.2(3) . . ?
C7 C8 C21 116.5(3) . . ?
C7 C8 C9 124.7(3) . . ?
C21 C8 C9 118.7(3) . . ?
C10 C9 C28 121.2(3) . . ?
C10 C9 C8 121.5(3) . . ?
C28 C9 C8 117.2(3) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C12 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 C14 119.4(3) . . ?
C13 C12 C14 119.2(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C29 111.9(2) . . ?
C12 C14 C4 114.3(2) . . ?
C29 C14 C4 110.5(2) . . ?
C12 C14 H14 106.6 . . ?
C29 C14 H14 106.6 . . ?
C4 C14 H14 106.6 . . ?
C3 C15 C16 121.4(2) . . ?
C3 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
O1 C16 C15 123.7(3) . . ?
O1 C16 C17 119.0(2) . . ?
C15 C16 C17 116.9(2) . . ?
O2 C17 C16 110.7(2) . . ?
O2 C17 C18 107.1(2) . . ?
C16 C17 C18 105.6(2) . . ?
O2 C17 C19 110.3(2) . . ?
C16 C17 C19 111.8(2) . . ?
C18 C17 C19 111.2(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 C20 110.4(2) . . ?
C17 C19 C4 114.3(2) . . ?
C20 C19 C4 110.9(2) . . ?
C17 C19 H19 106.9 . . ?
C20 C19 H19 106.9 . . ?
C4 C19 H19 106.9 . . ?
C7 C20 C25 108.5(2) . . ?
C7 C20 C19 108.4(2) . . ?
C25 C20 C19 109.2(2) . . ?
C7 C20 H20 110.2 . . ?
C25 C20 H20 110.2 . . ?
C19 C20 H20 110.2 . . ?
C22 C21 C8 122.1(3) . . ?
C22 C21 H21 119.0 . . ?
C8 C21 H21 119.0 . . ?
C21 C22 C23 122.0(3) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
C22 C23 C6 116.6(3) . . ?
C22 C23 C27 121.2(3) . . ?
C6 C23 C27 122.1(3) . . ?
O3 C24 C5 123.6(3) . . ?
O3 C24 C25 123.9(2) . . ?
C5 C24 C25 112.5(2) . . ?
O4 C25 C26 111.0(2) . . ?
O4 C25 C24 107.4(2) . . ?
C26 C25 C24 109.8(2) . . ?
O4 C25 C20 108.1(2) . . ?
C26 C25 C20 112.8(2) . . ?
C24 C25 C20 107.5(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C9 C28 H28A 109.5 . . ?
C9 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C9 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C1 C29 C14 114.0(2) . . ?
C1 C29 H29A 108.8 . . ?
C14 C29 H29A 108.8 . . ?
C1 C29 H29B 108.8 . . ?
C14 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C2 C30 H30A 109.5 . . ?
C2 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C2 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
C29 C1 C2 C3 0.5(4) . . . . ?
C29 C1 C2 C30 -177.6(3) . . . . ?
C1 C2 C3 C15 -175.4(3) . . . . ?
C30 C2 C3 C15 2.8(4) . . . . ?
C1 C2 C3 C4 13.8(4) . . . . ?
C30 C2 C3 C4 -168.0(2) . . . . ?
C15 C3 C4 C14 148.1(3) . . . . ?
C2 C3 C4 C14 -41.1(3) . . . . ?
C15 C3 C4 C19 19.6(4) . . . . ?
C2 C3 C4 C19 -169.6(2) . . . . ?
C15 C3 C4 C5 -96.6(3) . . . . ?
C2 C3 C4 C5 74.2(3) . . . . ?
C3 C4 C5 C6 70.1(3) . . . . ?
C14 C4 C5 C6 -172.4(2) . . . . ?
C19 C4 C5 C6 -52.8(3) . . . . ?
C3 C4 C5 C24 -174.5(2) . . . . ?
C14 C4 C5 C24 -56.9(3) . . . . ?
C19 C4 C5 C24 62.7(2) . . . . ?
C24 C5 C6 C7 -56.3(3) . . . . ?
C4 C5 C6 C7 59.5(3) . . . . ?
C24 C5 C6 C23 125.7(3) . . . . ?
C4 C5 C6 C23 -118.5(3) . . . . ?
C23 C6 C7 C8 0.4(4) . . . . ?
C5 C6 C7 C8 -177.6(2) . . . . ?
C23 C6 C7 C20 176.4(2) . . . . ?
C5 C6 C7 C20 -1.7(3) . . . . ?
C6 C7 C8 C21 -1.0(4) . . . . ?
C20 C7 C8 C21 -176.2(3) . . . . ?
C6 C7 C8 C9 176.1(3) . . . . ?
C20 C7 C8 C9 0.9(5) . . . . ?
C7 C8 C9 C10 51.4(5) . . . . ?
C21 C8 C9 C10 -131.5(3) . . . . ?
C7 C8 C9 C28 -131.6(4) . . . . ?
C21 C8 C9 C28 45.5(4) . . . . ?
C11 C12 C14 C29 132.2(3) . . . . ?
C13 C12 C14 C29 -44.7(4) . . . . ?
C11 C12 C14 C4 -101.4(3) . . . . ?
C13 C12 C14 C4 81.7(3) . . . . ?
C3 C4 C14 C12 -73.3(3) . . . . ?
C19 C4 C14 C12 57.9(3) . . . . ?
C5 C4 C14 C12 174.6(2) . . . . ?
C3 C4 C14 C29 53.9(3) . . . . ?
C19 C4 C14 C29 -174.9(2) . . . . ?
C5 C4 C14 C29 -58.3(3) . . . . ?
C2 C3 C15 C16 177.1(3) . . . . ?
C4 C3 C15 C16 -12.6(4) . . . . ?
C3 C15 C16 O1 165.0(3) . . . . ?
C3 C15 C16 C17 -22.4(4) . . . . ?
O1 C16 C17 O2 -16.4(4) . . . . ?
C15 C16 C17 O2 170.7(2) . . . . ?
O1 C16 C17 C18 99.2(3) . . . . ?
C15 C16 C17 C18 -73.8(3) . . . . ?
O1 C16 C17 C19 -139.7(3) . . . . ?
C15 C16 C17 C19 47.4(3) . . . . ?
O2 C17 C19 C20 -35.8(3) . . . . ?
C16 C17 C19 C20 87.8(3) . . . . ?
C18 C17 C19 C20 -154.4(2) . . . . ?
O2 C17 C19 C4 -161.7(2) . . . . ?
C16 C17 C19 C4 -38.1(3) . . . . ?
C18 C17 C19 C4 79.7(3) . . . . ?
C3 C4 C19 C17 7.2(3) . . . . ?
C14 C4 C19 C17 -121.2(2) . . . . ?
C5 C4 C19 C17 121.3(2) . . . . ?
C3 C4 C19 C20 -118.4(2) . . . . ?
C14 C4 C19 C20 113.1(2) . . . . ?
C5 C4 C19 C20 -4.3(3) . . . . ?
C6 C7 C20 C25 60.2(3) . . . . ?
C8 C7 C20 C25 -124.2(3) . . . . ?
C6 C7 C20 C19 -58.2(3) . . . . ?
C8 C7 C20 C19 117.4(3) . . . . ?
C17 C19 C20 C7 -67.8(3) . . . . ?
C4 C19 C20 C7 60.0(3) . . . . ?
C17 C19 C20 C25 174.1(2) . . . . ?
C4 C19 C20 C25 -58.0(3) . . . . ?
C7 C8 C21 C22 0.8(5) . . . . ?
C9 C8 C21 C22 -176.5(3) . . . . ?
C8 C21 C22 C23 0.0(5) . . . . ?
C21 C22 C23 C6 -0.5(4) . . . . ?
C21 C22 C23 C27 177.9(3) . . . . ?
C7 C6 C23 C22 0.3(4) . . . . ?
C5 C6 C23 C22 178.2(3) . . . . ?
C7 C6 C23 C27 -178.1(3) . . . . ?
C5 C6 C23 C27 -0.2(4) . . . . ?
C6 C5 C24 O3 -124.4(3) . . . . ?
C4 C5 C24 O3 118.4(3) . . . . ?
C6 C5 C24 C25 56.4(3) . . . . ?
C4 C5 C24 C25 -60.7(3) . . . . ?
O3 C24 C25 O4 -64.5(4) . . . . ?
C5 C24 C25 O4 114.6(2) . . . . ?
O3 C24 C25 C26 56.3(4) . . . . ?
C5 C24 C25 C26 -124.6(3) . . . . ?
O3 C24 C25 C20 179.3(3) . . . . ?
C5 C24 C25 C20 -1.5(3) . . . . ?
C7 C20 C25 O4 -172.0(2) . . . . ?
C19 C20 C25 O4 -54.1(3) . . . . ?
C7 C20 C25 C26 64.9(3) . . . . ?
C19 C20 C25 C26 -177.2(2) . . . . ?
C7 C20 C25 C24 -56.4(3) . . . . ?
C19 C20 C25 C24 61.6(3) . . . . ?
C2 C1 C29 C14 14.2(4) . . . . ?
C12 C14 C29 C1 87.7(3) . . . . ?
C4 C14 C29 C1 -40.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C26 H26C O2 0.98 2.63 3.139(3) 112.7 3_656
O4 H4 O1 0.84 1.92 2.749(3) 171.1 1_455
O2 H2 O1 0.84 2.14 2.639(3) 117.5 .
C26 H26C O2 0.98 2.63 3.139(3) 112.7 3_656
O4 H4 O1 0.84 1.92 2.749(3) 171.1 1_455
O2 H2 O1 0.84 2.14 2.639(3) 117.5 .
C26 H26C O2 0.98 2.63 3.139(3) 112.7 3_656
O4 H4 O1 0.84 1.92 2.749(3) 171.1 1_455
O2 H2 O1 0.84 2.14 2.639(3) 117.5 .
C26 H26C O2 0.98 2.63 3.139(3) 112.7 3_656
O4 H4 O1 0.84 1.92 2.749(3) 171.1 1_455
O2 H2 O1 0.84 2.14 2.639(3) 117.5 .
O2 H2 O1 0.84 2.14 2.639(3) 117.5 .
O4 H4 O1 0.84 1.92 2.749(3) 171.1 1_455
C26 H26C O2 0.98 2.63 3.139(3) 112.7 3_656
O2 H2 O1 0.84 2.14 2.639(3) 117.5 .
O4 H4 O1 0.84 1.92 2.749(3) 171.1 1_455
C26 H26C O2 0.98 2.63 3.139(3) 112.7 3_656
O2 H2 O1 0.84 2.14 2.639(3) 117.5 .
O4 H4 O1 0.84 1.92 2.749(3) 171.1 1_455
C26 H26C O2 0.98 2.63 3.139(3) 112.7 3_656
O2 H2 O1 0.84 2.14 2.639(3) 117.5 .
O4 H4 O1 0.84 1.92 2.749(3) 171.1 1_455
C26 H26C O2 0.98 2.63 3.139(3) 112.7 3_656

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.111

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_she154_0m
_database_code_depnum_ccdc_archive 'CCDC 2212937'
loop_
_audit_author_name
_audit_author_address
'Xiao-Nian Li'
;Kunming Institute of Botany
China
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-11-28 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         'C30 H38 O4'
_chemical_formula_sum            'C30 H38 O4'
_chemical_formula_weight         462.60

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                   8.8971(2)
_cell_length_b                   15.2326(3)
_cell_length_c                   18.8392(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2553.20(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      70.18

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   0.3967
_exptl_transmission_factor_max   0.5857
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.570
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.617
_shelx_estimated_absorpt_T_min   0.607
_shelx_estimated_absorpt_T_max   0.790
_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      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15802
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.732
_diffrn_reflns_theta_max         70.288
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             4650
_reflns_number_gt                4642
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_max     0.918
_reflns_Friedel_fraction_full    0.956

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.6653P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0046(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1903 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4650
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25181(15) -0.04935(8) 0.21071(8) 0.0225(3) Uani 1 1 d . . . . .
O2 O 0.52262(15) 0.03550(9) 0.20733(8) 0.0212(3) Uani 1 1 d . . . . .
H11 H 0.544(3) -0.009(2) 0.1820(15) 0.032 Uiso 1 1 d . U . . .
O3 O 0.30590(16) 0.38403(9) 0.33915(8) 0.0231(3) Uani 1 1 d . . . . .
O4 O 0.56098(16) 0.31587(9) 0.25378(8) 0.0204(3) Uani 1 1 d . . . . .
H20 H 0.611(3) 0.357(2) 0.2692(15) 0.031 Uiso 1 1 d . U . . .
C1 C 0.4178(3) 0.32731(14) 0.07196(12) 0.0307(5) Uani 1 1 d . . . . .
H37 H 0.4443 0.3254 0.0231 0.037 Uiso 1 1 calc R U . . .
H1 H 0.4883 0.3479 0.1060 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2828(2) 0.30137(13) 0.09257(11) 0.0233(4) Uani 1 1 d . . . . .
C3 C 0.2392(2) 0.30969(12) 0.17024(10) 0.0177(4) Uani 1 1 d . . . . .
H36 H 0.3176 0.3474 0.1930 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2371(2) 0.22139(12) 0.21292(10) 0.0154(4) Uani 1 1 d . . . . .
C5 C 0.3939(2) 0.17379(11) 0.21072(10) 0.0144(4) Uani 1 1 d . . . . .
H12 H 0.4610 0.2100 0.1797 0.017 Uiso 1 1 calc R U . . .
C6 C 0.4643(2) 0.17470(12) 0.28659(10) 0.0170(4) Uani 1 1 d . . . . .
H13 H 0.5631 0.1434 0.2862 0.020 Uiso 1 1 calc R U . . .
C7 C 0.3564(2) 0.12905(12) 0.33683(10) 0.0181(4) Uani 1 1 d . . . . .
C8 C 0.3965(2) 0.04249(13) 0.37243(11) 0.0214(4) Uani 1 1 d . . . . .
H31 H 0.4365 0.0036 0.3341 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5232(3) 0.05244(13) 0.42649(14) 0.0333(6) Uani 1 1 d . . . . .
C10 C 0.4866(4) 0.0720(2) 0.50082(15) 0.0521(8) Uani 1 1 d . . . . .
H15 H 0.5795 0.0753 0.5286 0.078 Uiso 1 1 calc R U . . .
H2 H 0.4222 0.0255 0.5200 0.078 Uiso 1 1 calc R U . . .
H14 H 0.4337 0.1284 0.5035 0.078 Uiso 1 1 calc R U . . .
C11 C 0.1691(3) 0.26853(17) 0.04001(12) 0.0350(5) Uani 1 1 d . . . . .
H3 H 0.2151 0.2655 -0.0072 0.053 Uiso 1 1 calc R U . . .
H4 H 0.0832 0.3087 0.0387 0.053 Uiso 1 1 calc R U . . .
H38 H 0.1349 0.2099 0.0542 0.053 Uiso 1 1 calc R U . . .
C12 C 0.1033(2) 0.16591(12) 0.19192(10) 0.0166(4) Uani 1 1 d . . . . .
C13 C -0.0408(2) 0.21151(13) 0.18130(11) 0.0213(4) Uani 1 1 d . . . . .
C14 C -0.1820(2) 0.15759(15) 0.17417(13) 0.0280(5) Uani 1 1 d . . . . .
H6 H -0.2689 0.1967 0.1702 0.042 Uiso 1 1 calc R U . . .
H5 H -0.1935 0.1201 0.2161 0.042 Uiso 1 1 calc R U . . .
H7 H -0.1752 0.1208 0.1316 0.042 Uiso 1 1 calc R U . . .
C15 C -0.0459(2) 0.29909(13) 0.17692(12) 0.0245(4) Uani 1 1 d . . . . .
H10 H -0.1418 0.3257 0.1718 0.029 Uiso 1 1 calc R U . . .
C16 C 0.0881(2) 0.35844(13) 0.17944(12) 0.0224(4) Uani 1 1 d . . . . .
H9 H 0.0889 0.3897 0.2255 0.027 Uiso 1 1 calc R U . . .
H8 H 0.0786 0.4030 0.1415 0.027 Uiso 1 1 calc R U . . .
C17 C 0.1107(2) 0.07754(13) 0.19002(10) 0.0179(4) Uani 1 1 d . . . . .
H35 H 0.0203 0.0453 0.1835 0.021 Uiso 1 1 calc R U . . .
C18 C 0.2508(2) 0.02944(12) 0.19750(10) 0.0172(4) Uani 1 1 d . . . . .
C19 C 0.3945(2) 0.07919(12) 0.17977(10) 0.0167(4) Uani 1 1 d . . . . .
C20 C 0.6668(3) 0.04250(17) 0.40450(19) 0.0472(7) Uani 1 1 d . . . . .
H16 H 0.7470 0.0482 0.4374 0.057 Uiso 1 1 calc R U . . .
H17 H 0.6874 0.0298 0.3561 0.057 Uiso 1 1 calc R U . . .
C21 C 0.2519(3) -0.00183(14) 0.39978(12) 0.0270(5) Uani 1 1 d . . . . .
H30 H 0.2022 -0.0320 0.3596 0.032 Uiso 1 1 calc R U . . .
H29 H 0.2798 -0.0471 0.4352 0.032 Uiso 1 1 calc R U . . .
C22 C 0.1402(3) 0.06117(15) 0.43356(12) 0.0298(5) Uani 1 1 d . . . . .
H28 H 0.1871 0.0886 0.4757 0.036 Uiso 1 1 calc R U . . .
H27 H 0.0513 0.0277 0.4498 0.036 Uiso 1 1 calc R U . . .
C23 C 0.0894(2) 0.13297(13) 0.38259(10) 0.0219(4) Uani 1 1 d . . . . .
H18 H 0.0155 0.1067 0.3487 0.026 Uiso 1 1 calc R U . . .
C24 C 0.2215(2) 0.16680(12) 0.34030(10) 0.0179(4) Uani 1 1 d . . . . .
C25 C 0.2057(2) 0.24710(12) 0.29409(10) 0.0173(4) Uani 1 1 d . . . . .
H19 H 0.1040 0.2742 0.2997 0.021 Uiso 1 1 calc R U . . .
C26 C 0.3283(2) 0.31022(12) 0.31733(10) 0.0184(4) Uani 1 1 d . . . . .
C27 C 0.4864(2) 0.27065(12) 0.30977(10) 0.0183(4) Uani 1 1 d . . . . .
C28 C 0.5729(2) 0.27852(14) 0.37912(11) 0.0247(4) Uani 1 1 d . . . . .
H21 H 0.6754 0.2565 0.3724 0.037 Uiso 1 1 calc R U . . .
H22 H 0.5224 0.2439 0.4159 0.037 Uiso 1 1 calc R U . . .
H23 H 0.5766 0.3402 0.3937 0.037 Uiso 1 1 calc R U . . .
C29 C 0.0099(3) 0.20660(16) 0.42364(12) 0.0317(5) Uani 1 1 d . . . . .
H26 H 0.0830 0.2376 0.4534 0.048 Uiso 1 1 calc R U . . .
H24 H -0.0688 0.1813 0.4538 0.048 Uiso 1 1 calc R U . . .
H25 H -0.0355 0.2479 0.3900 0.048 Uiso 1 1 calc R U . . .
C30 C 0.4048(2) 0.08096(14) 0.09820(11) 0.0233(4) Uani 1 1 d . . . . .
H33 H 0.4978 0.1106 0.0839 0.035 Uiso 1 1 calc R U . . .
H32 H 0.3182 0.1127 0.0788 0.035 Uiso 1 1 calc R U . . .
H34 H 0.4050 0.0207 0.0800 0.035 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 C18 1.226(2) . ?
O2 C19 1.418(2) . ?
O2 H11 0.85(3) . ?
O3 C26 1.214(2) . ?
O4 C27 1.424(2) . ?
O4 H20 0.82(3) . ?
C1 C2 1.323(3) . ?
C1 H37 0.9500 . ?
C1 H1 0.9500 . ?
C2 C11 1.501(3) . ?
C2 C3 1.519(3) . ?
C3 C16 1.546(3) . ?
C3 C4 1.567(2) . ?
C3 H36 1.0000 . ?
C4 C12 1.512(3) . ?
C4 C5 1.573(2) . ?
C4 C25 1.603(2) . ?
C5 C19 1.555(2) . ?
C5 C6 1.561(3) . ?
C5 H12 1.0000 . ?
C6 C7 1.517(3) . ?
C6 C27 1.538(2) . ?
C6 H13 1.0000 . ?
C7 C24 1.333(3) . ?
C7 C8 1.522(3) . ?
C8 C9 1.527(3) . ?
C8 C21 1.541(3) . ?
C8 H31 1.0000 . ?
C9 C20 1.351(4) . ?
C9 C10 1.469(4) . ?
C10 H15 0.9800 . ?
C10 H2 0.9800 . ?
C10 H14 0.9800 . ?
C11 H3 0.9800 . ?
C11 H4 0.9800 . ?
C11 H38 0.9800 . ?
C12 C17 1.348(3) . ?
C12 C13 1.472(3) . ?
C13 C15 1.337(3) . ?
C13 C14 1.506(3) . ?
C14 H6 0.9800 . ?
C14 H5 0.9800 . ?
C14 H7 0.9800 . ?
C15 C16 1.497(3) . ?
C15 H10 0.9500 . ?
C16 H9 0.9900 . ?
C16 H8 0.9900 . ?
C17 C18 1.453(3) . ?
C17 H35 0.9500 . ?
C18 C19 1.523(3) . ?
C19 C30 1.540(3) . ?
C20 H16 0.9500 . ?
C20 H17 0.9500 . ?
C21 C22 1.521(3) . ?
C21 H30 0.9900 . ?
C21 H29 0.9900 . ?
C22 C23 1.524(3) . ?
C22 H28 0.9900 . ?
C22 H27 0.9900 . ?
C23 C24 1.510(3) . ?
C23 C29 1.535(3) . ?
C23 H18 1.0000 . ?
C24 C25 1.508(3) . ?
C25 C26 1.519(3) . ?
C25 H19 1.0000 . ?
C26 C27 1.537(3) . ?
C27 C28 1.521(3) . ?
C28 H21 0.9800 . ?
C28 H22 0.9800 . ?
C28 H23 0.9800 . ?
C29 H26 0.9800 . ?
C29 H24 0.9800 . ?
C29 H25 0.9800 . ?
C30 H33 0.9800 . ?
C30 H32 0.9800 . ?
C30 H34 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O2 H11 110.2(19) . . ?
C27 O4 H20 111.1(19) . . ?
C2 C1 H37 120.0 . . ?
C2 C1 H1 120.0 . . ?
H37 C1 H1 120.0 . . ?
C1 C2 C11 121.2(2) . . ?
C1 C2 C3 119.3(2) . . ?
C11 C2 C3 119.42(19) . . ?
C2 C3 C16 111.72(17) . . ?
C2 C3 C4 115.20(15) . . ?
C16 C3 C4 110.13(15) . . ?
C2 C3 H36 106.4 . . ?
C16 C3 H36 106.4 . . ?
C4 C3 H36 106.4 . . ?
C12 C4 C3 110.79(15) . . ?
C12 C4 C5 115.71(14) . . ?
C3 C4 C5 111.78(14) . . ?
C12 C4 C25 104.41(14) . . ?
C3 C4 C25 106.37(14) . . ?
C5 C4 C25 107.00(14) . . ?
C19 C5 C6 110.52(15) . . ?
C19 C5 C4 116.10(14) . . ?
C6 C5 C4 109.12(14) . . ?
C19 C5 H12 106.9 . . ?
C6 C5 H12 106.9 . . ?
C4 C5 H12 106.9 . . ?
C7 C6 C27 109.84(15) . . ?
C7 C6 C5 108.27(15) . . ?
C27 C6 C5 108.65(15) . . ?
C7 C6 H13 110.0 . . ?
C27 C6 H13 110.0 . . ?
C5 C6 H13 110.0 . . ?
C24 C7 C6 113.76(16) . . ?
C24 C7 C8 124.29(18) . . ?
C6 C7 C8 121.59(17) . . ?
C7 C8 C9 112.40(16) . . ?
C7 C8 C21 109.34(17) . . ?
C9 C8 C21 115.90(18) . . ?
C7 C8 H31 106.2 . . ?
C9 C8 H31 106.2 . . ?
C21 C8 H31 106.2 . . ?
C20 C9 C10 121.7(2) . . ?
C20 C9 C8 118.8(3) . . ?
C10 C9 C8 119.5(2) . . ?
C9 C10 H15 109.5 . . ?
C9 C10 H2 109.5 . . ?
H15 C10 H2 109.5 . . ?
C9 C10 H14 109.5 . . ?
H15 C10 H14 109.5 . . ?
H2 C10 H14 109.5 . . ?
C2 C11 H3 109.5 . . ?
C2 C11 H4 109.5 . . ?
H3 C11 H4 109.5 . . ?
C2 C11 H38 109.5 . . ?
H3 C11 H38 109.5 . . ?
H4 C11 H38 109.5 . . ?
C17 C12 C13 120.67(17) . . ?
C17 C12 C4 121.76(17) . . ?
C13 C12 C4 117.23(16) . . ?
C15 C13 C12 120.55(18) . . ?
C15 C13 C14 120.69(18) . . ?
C12 C13 C14 118.75(17) . . ?
C13 C14 H6 109.5 . . ?
C13 C14 H5 109.5 . . ?
H6 C14 H5 109.5 . . ?
C13 C14 H7 109.5 . . ?
H6 C14 H7 109.5 . . ?
H5 C14 H7 109.5 . . ?
C13 C15 C16 125.02(18) . . ?
C13 C15 H10 117.5 . . ?
C16 C15 H10 117.5 . . ?
C15 C16 C3 113.52(15) . . ?
C15 C16 H9 108.9 . . ?
C3 C16 H9 108.9 . . ?
C15 C16 H8 108.9 . . ?
C3 C16 H8 108.9 . . ?
H9 C16 H8 107.7 . . ?
C12 C17 C18 122.89(17) . . ?
C12 C17 H35 118.6 . . ?
C18 C17 H35 118.6 . . ?
O1 C18 C17 121.33(17) . . ?
O1 C18 C19 121.70(17) . . ?
C17 C18 C19 116.61(15) . . ?
O2 C19 C18 111.16(15) . . ?
O2 C19 C30 109.00(16) . . ?
C18 C19 C30 106.11(15) . . ?
O2 C19 C5 107.47(14) . . ?
C18 C19 C5 112.11(15) . . ?
C30 C19 C5 110.99(16) . . ?
C9 C20 H16 120.0 . . ?
C9 C20 H17 120.0 . . ?
H16 C20 H17 120.0 . . ?
C22 C21 C8 114.13(17) . . ?
C22 C21 H30 108.7 . . ?
C8 C21 H30 108.7 . . ?
C22 C21 H29 108.7 . . ?
C8 C21 H29 108.7 . . ?
H30 C21 H29 107.6 . . ?
C21 C22 C23 112.52(18) . . ?
C21 C22 H28 109.1 . . ?
C23 C22 H28 109.1 . . ?
C21 C22 H27 109.1 . . ?
C23 C22 H27 109.1 . . ?
H28 C22 H27 107.8 . . ?
C24 C23 C22 110.28(17) . . ?
C24 C23 C29 112.03(17) . . ?
C22 C23 C29 110.10(18) . . ?
C24 C23 H18 108.1 . . ?
C22 C23 H18 108.1 . . ?
C29 C23 H18 108.1 . . ?
C7 C24 C25 113.93(16) . . ?
C7 C24 C23 125.41(18) . . ?
C25 C24 C23 120.59(17) . . ?
C24 C25 C26 106.27(15) . . ?
C24 C25 C4 109.65(14) . . ?
C26 C25 C4 107.72(15) . . ?
C24 C25 H19 111.0 . . ?
C26 C25 H19 111.0 . . ?
C4 C25 H19 111.0 . . ?
O3 C26 C25 124.47(18) . . ?
O3 C26 C27 123.04(17) . . ?
C25 C26 C27 112.49(15) . . ?
O4 C27 C28 111.25(16) . . ?
O4 C27 C26 107.78(15) . . ?
C28 C27 C26 110.65(16) . . ?
O4 C27 C6 107.99(15) . . ?
C28 C27 C6 112.54(16) . . ?
C26 C27 C6 106.38(15) . . ?
C27 C28 H21 109.5 . . ?
C27 C28 H22 109.5 . . ?
H21 C28 H22 109.5 . . ?
C27 C28 H23 109.5 . . ?
H21 C28 H23 109.5 . . ?
H22 C28 H23 109.5 . . ?
C23 C29 H26 109.5 . . ?
C23 C29 H24 109.5 . . ?
H26 C29 H24 109.5 . . ?
C23 C29 H25 109.5 . . ?
H26 C29 H25 109.5 . . ?
H24 C29 H25 109.5 . . ?
C19 C30 H33 109.5 . . ?
C19 C30 H32 109.5 . . ?
H33 C30 H32 109.5 . . ?
C19 C30 H34 109.5 . . ?
H33 C30 H34 109.5 . . ?
H32 C30 H34 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
C1 C2 C3 C16 127.9(2) . . . . ?
C11 C2 C3 C16 -48.7(2) . . . . ?
C1 C2 C3 C4 -105.4(2) . . . . ?
C11 C2 C3 C4 77.9(2) . . . . ?
C2 C3 C4 C12 -72.9(2) . . . . ?
C16 C3 C4 C12 54.6(2) . . . . ?
C2 C3 C4 C5 57.8(2) . . . . ?
C16 C3 C4 C5 -174.79(15) . . . . ?
C2 C3 C4 C25 174.22(16) . . . . ?
C16 C3 C4 C25 -58.33(19) . . . . ?
C12 C4 C5 C19 6.2(2) . . . . ?
C3 C4 C5 C19 -121.84(17) . . . . ?
C25 C4 C5 C19 122.08(16) . . . . ?
C12 C4 C5 C6 -119.42(17) . . . . ?
C3 C4 C5 C6 112.51(16) . . . . ?
C25 C4 C5 C6 -3.57(18) . . . . ?
C19 C5 C6 C7 -70.36(18) . . . . ?
C4 C5 C6 C7 58.46(18) . . . . ?
C19 C5 C6 C27 170.38(15) . . . . ?
C4 C5 C6 C27 -60.79(19) . . . . ?
C27 C6 C7 C24 58.8(2) . . . . ?
C5 C6 C7 C24 -59.7(2) . . . . ?
C27 C6 C7 C8 -127.74(18) . . . . ?
C5 C6 C7 C8 113.76(18) . . . . ?
C24 C7 C8 C9 -119.4(2) . . . . ?
C6 C7 C8 C9 67.9(2) . . . . ?
C24 C7 C8 C21 10.8(3) . . . . ?
C6 C7 C8 C21 -161.92(17) . . . . ?
C7 C8 C9 C20 -90.0(2) . . . . ?
C21 C8 C9 C20 143.3(2) . . . . ?
C7 C8 C9 C10 90.3(3) . . . . ?
C21 C8 C9 C10 -36.4(3) . . . . ?
C3 C4 C12 C17 145.59(18) . . . . ?
C5 C4 C12 C17 17.0(3) . . . . ?
C25 C4 C12 C17 -100.3(2) . . . . ?
C3 C4 C12 C13 -41.1(2) . . . . ?
C5 C4 C12 C13 -169.66(16) . . . . ?
C25 C4 C12 C13 73.0(2) . . . . ?
C17 C12 C13 C15 -174.0(2) . . . . ?
C4 C12 C13 C15 12.6(3) . . . . ?
C17 C12 C13 C14 4.9(3) . . . . ?
C4 C12 C13 C14 -168.49(18) . . . . ?
C12 C13 C15 C16 2.3(3) . . . . ?
C14 C13 C15 C16 -176.6(2) . . . . ?
C13 C15 C16 C3 13.4(3) . . . . ?
C2 C3 C16 C15 88.3(2) . . . . ?
C4 C3 C16 C15 -41.1(2) . . . . ?
C13 C12 C17 C18 177.61(17) . . . . ?
C4 C12 C17 C18 -9.3(3) . . . . ?
C12 C17 C18 O1 164.21(19) . . . . ?
C12 C17 C18 C19 -22.6(3) . . . . ?
O1 C18 C19 O2 -23.2(2) . . . . ?
C17 C18 C19 O2 163.64(16) . . . . ?
O1 C18 C19 C30 95.2(2) . . . . ?
C17 C18 C19 C30 -78.0(2) . . . . ?
O1 C18 C19 C5 -143.51(18) . . . . ?
C17 C18 C19 C5 43.3(2) . . . . ?
C6 C5 C19 O2 -31.87(19) . . . . ?
C4 C5 C19 O2 -156.82(15) . . . . ?
C6 C5 C19 C18 90.56(18) . . . . ?
C4 C5 C19 C18 -34.4(2) . . . . ?
C6 C5 C19 C30 -150.97(16) . . . . ?
C4 C5 C19 C30 84.08(19) . . . . ?
C7 C8 C21 C22 -40.9(2) . . . . ?
C9 C8 C21 C22 87.4(2) . . . . ?
C8 C21 C22 C23 59.0(2) . . . . ?
C21 C22 C23 C24 -41.7(2) . . . . ?
C21 C22 C23 C29 -165.87(18) . . . . ?
C6 C7 C24 C25 -0.5(2) . . . . ?
C8 C7 C24 C25 -173.73(17) . . . . ?
C6 C7 C24 C23 176.45(17) . . . . ?
C8 C7 C24 C23 3.2(3) . . . . ?
C22 C23 C24 C7 12.4(3) . . . . ?
C29 C23 C24 C7 135.4(2) . . . . ?
C22 C23 C24 C25 -170.84(17) . . . . ?
C29 C23 C24 C25 -47.8(2) . . . . ?
C7 C24 C25 C26 -57.3(2) . . . . ?
C23 C24 C25 C26 125.54(17) . . . . ?
C7 C24 C25 C4 58.8(2) . . . . ?
C23 C24 C25 C4 -118.30(18) . . . . ?
C12 C4 C25 C24 69.96(18) . . . . ?
C3 C4 C25 C24 -172.81(15) . . . . ?
C5 C4 C25 C24 -53.19(18) . . . . ?
C12 C4 C25 C26 -174.80(15) . . . . ?
C3 C4 C25 C26 -57.58(18) . . . . ?
C5 C4 C25 C26 62.05(18) . . . . ?
C24 C25 C26 O3 -121.4(2) . . . . ?
C4 C25 C26 O3 121.12(19) . . . . ?
C24 C25 C26 C27 59.0(2) . . . . ?
C4 C25 C26 C27 -58.47(19) . . . . ?
O3 C26 C27 O4 -68.9(2) . . . . ?
C25 C26 C27 O4 110.67(17) . . . . ?
O3 C26 C27 C28 52.9(2) . . . . ?
C25 C26 C27 C28 -127.48(17) . . . . ?
O3 C26 C27 C6 175.45(17) . . . . ?
C25 C26 C27 C6 -4.9(2) . . . . ?
C7 C6 C27 O4 -167.69(15) . . . . ?
C5 C6 C27 O4 -49.4(2) . . . . ?
C7 C6 C27 C28 69.1(2) . . . . ?
C5 C6 C27 C28 -172.62(16) . . . . ?
C7 C6 C27 C26 -52.21(19) . . . . ?
C5 C6 C27 C26 66.05(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H20 O1 0.82(3) 1.91(3) 2.7271(19) 170(3) 3_655
O2 H11 O3 0.85(3) 2.15(3) 2.901(2) 148(3) 3_645
O4 H20 O1 0.82(3) 1.91(3) 2.7271(19) 170(3) 3_655
O2 H11 O3 0.85(3) 2.15(3) 2.901(2) 148(3) 3_645
O4 H20 O1 0.82(3) 1.91(3) 2.7271(19) 170(3) 3_655
O2 H11 O3 0.85(3) 2.15(3) 2.901(2) 148(3) 3_645
O4 H20 O1 0.82(3) 1.91(3) 2.7271(19) 170(3) 3_655
O2 H11 O3 0.85(3) 2.15(3) 2.901(2) 148(3) 3_645
O4 H20 O1 0.82(3) 1.91(3) 2.7271(19) 170(3) 3_655
O2 H11 O3 0.85(3) 2.15(3) 2.901(2) 148(3) 3_645
O2 H11 O3 0.85(3) 2.15(3) 2.901(2) 148(3) 3_645
O4 H20 O1 0.82(3) 1.91(3) 2.7271(19) 170(3) 3_655
O2 H11 O3 0.85(3) 2.15(3) 2.901(2) 148(3) 3_645
O4 H20 O1 0.82(3) 1.91(3) 2.7271(19) 170(3) 3_655
O2 H11 O3 0.85(3) 2.15(3) 2.901(2) 148(3) 3_645
O4 H20 O1 0.82(3) 1.91(3) 2.7271(19) 170(3) 3_655
O2 H11 O3 0.85(3) 2.15(3) 2.901(2) 148(3) 3_645
O4 H20 O1 0.82(3) 1.91(3) 2.7271(19) 170(3) 3_655
O2 H11 O3 0.85(3) 2.15(3) 2.901(2) 148(3) 3_645
O4 H20 O1 0.82(3) 1.91(3) 2.7271(19) 170(3) 3_655

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_she155
_database_code_depnum_ccdc_archive 'CCDC 2212938'
loop_
_audit_author_name
_audit_author_address
'Xiao-Nian Li'
;Kunming Institute of Botany
China
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C30 H38 O4, H2 O'
_chemical_formula_sum            'C30 H40 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         480.62
_chemical_absolute_configuration ad

_chemical_melting_point          ?

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

_cell_length_a                   8.7065(2)
_cell_length_b                   13.1797(2)
_cell_length_c                   22.9727(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2636.10(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9825
_cell_measurement_theta_min      5.4336
_cell_measurement_theta_max      72.3199
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.510
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040

_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            20914
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         72.31
_diffrn_reflns_theta_full        72.31
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             5192
_reflns_number_gt                5073
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0806
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_number_reflns         5192
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.5759P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 2176 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O5 0.68124(15) 0.76268(11) 0.45809(7) 0.0265(3) Uani d . . . 1 . .
H H39 0.735713 0.811845 0.444928 0.04 Uiso d U . R 1 . .
H H40 0.589123 0.787972 0.464759 0.04 Uiso d U . R 1 . .
O O1 0.33280(14) 0.43950(10) 0.65949(6) 0.0220(3) Uani d . . . 1 . .
O O2 0.37511(14) 0.58008(10) 0.58082(6) 0.0171(3) Uani d . . . 1 . .
H H37 0.311(3) 0.543(2) 0.5870(5) 0.026 Uiso calc U . R 1 . .
O O3 1.07789(14) 0.49896(10) 0.56092(5) 0.0180(3) Uani d . . . 1 . .
O O4 0.87381(14) 0.66748(9) 0.53067(5) 0.0147(2) Uani d . . . 1 . .
H H38 0.815(3) 0.7004(12) 0.5114(11) 0.022 Uiso calc U . R 1 . .
C C1 0.7691(2) 0.41859(17) 0.80624(8) 0.0255(4) Uani d . . . 1 . .
H H15 0.855929 0.408969 0.83282 0.038 Uiso calc U . R 1 . .
H H1 0.73235 0.352341 0.792773 0.038 Uiso calc U . R 1 . .
H H16 0.685975 0.453941 0.82663 0.038 Uiso calc U . R 1 . .
C C2 0.8198(2) 0.48076(14) 0.75481(7) 0.0188(4) Uani d . . . 1 . .
C C3 0.70779(19) 0.50218(13) 0.70797(7) 0.0144(3) Uani d . . . 1 . .
C C4 0.76896(18) 0.55014(12) 0.65232(7) 0.0123(3) Uani d . . . 1 . .
C C5 0.64642(18) 0.59191(12) 0.60806(7) 0.0117(3) Uani d . . . 1 . .
H H10 0.668416 0.665858 0.602998 0.014 Uiso calc U . R 1 . .
C C6 0.66841(18) 0.54172(12) 0.54729(7) 0.0116(3) Uani d . . . 1 . .
H H29 0.592608 0.56989 0.518859 0.014 Uiso calc U . R 1 . .
C C7 0.64632(18) 0.42843(12) 0.55376(7) 0.0125(3) Uani d . . . 1 . .
C C8 0.52137(19) 0.37054(13) 0.52107(8) 0.0151(3) Uani d . . . 1 . .
H H34 0.421407 0.387847 0.540068 0.018 Uiso calc U . R 1 . .
C C9 0.5077(2) 0.40137(14) 0.45696(8) 0.0217(4) Uani d . . . 1 . .
C C10 0.6051(3) 0.3529(2) 0.41421(10) 0.0478(8) Uani d . . . 1 . .
H H2 0.571039 0.28276 0.408311 0.072 Uiso calc U . R 1 . .
H H36 0.711583 0.353065 0.428029 0.072 Uiso calc U . R 1 . .
H H35 0.598627 0.389963 0.377313 0.072 Uiso calc U . R 1 . .
C C11 0.3988(4) 0.47178(19) 0.44153(11) 0.0487(8) Uani d . . . 1 . .
H H3 0.385729 0.489861 0.401803 0.058 Uiso calc U . R 1 . .
H H4 0.336463 0.502392 0.470578 0.058 Uiso calc U . R 1 . .
C C12 0.5443(2) 0.25541(13) 0.52818(9) 0.0216(4) Uani d . . . 1 . .
H H33 0.449606 0.219508 0.516171 0.026 Uiso calc U . R 1 . .
H H32 0.62905 0.232576 0.502592 0.026 Uiso calc U . R 1 . .
C C13 0.5819(2) 0.22880(14) 0.59115(9) 0.0217(4) Uani d . . . 1 . .
H H31 0.585212 0.154119 0.595628 0.026 Uiso calc U . R 1 . .
H H5 0.500337 0.255377 0.616995 0.026 Uiso calc U . R 1 . .
C C14 0.7366(2) 0.27392(13) 0.60903(8) 0.0162(3) Uani d . . . 1 . .
H H6 0.817574 0.239554 0.585253 0.019 Uiso calc U . R 1 . .
C C15 0.7691(2) 0.24928(14) 0.67295(8) 0.0240(4) Uani d . . . 1 . .
H H7 0.866774 0.280133 0.684558 0.036 Uiso calc U . R 1 . .
H H8 0.775018 0.175548 0.677973 0.036 Uiso calc U . R 1 . .
H H9 0.686127 0.276382 0.697242 0.036 Uiso calc U . R 1 . .
C C16 0.73992(19) 0.38578(12) 0.59345(7) 0.0132(3) Uani d . . . 1 . .
C C17 0.85535(19) 0.45949(13) 0.61972(7) 0.0125(3) Uani d . . . 1 . .
H H30 0.92756 0.423687 0.646625 0.015 Uiso calc U . R 1 . .
C C18 0.47714(18) 0.58360(13) 0.62914(7) 0.0136(3) Uani d . . . 1 . .
C C19 0.4348(2) 0.67629(14) 0.66631(9) 0.0198(4) Uani d . . . 1 . .
H H13 0.44168 0.737819 0.642508 0.03 Uiso calc U . R 1 . .
H H11 0.505956 0.681535 0.699224 0.03 Uiso calc U . R 1 . .
H H12 0.329669 0.668663 0.680935 0.03 Uiso calc U . R 1 . .
C C20 0.44972(19) 0.48923(13) 0.66620(8) 0.0158(3) Uani d . . . 1 . .
C C21 0.5616(2) 0.46945(13) 0.71191(7) 0.0170(3) Uani d . . . 1 . .
H H14 0.53069 0.432463 0.745413 0.02 Uiso calc U . R 1 . .
C C22 0.9614(2) 0.52022(15) 0.75262(8) 0.0200(4) Uani d . . . 1 . .
H H25 1.030538 0.503458 0.783146 0.024 Uiso calc U . R 1 . .
C C23 1.01854(19) 0.58889(14) 0.70544(8) 0.0171(3) Uani d . . . 1 . .
H H24 1.089288 0.550269 0.679997 0.021 Uiso calc U . R 1 . .
H H23 1.077808 0.644892 0.723332 0.021 Uiso calc U . R 1 . .
C C24 0.88989(19) 0.63425(13) 0.66794(7) 0.0140(3) Uani d . . . 1 . .
H H22 0.938288 0.655841 0.630463 0.017 Uiso calc U . R 1 . .
C C25 0.8211(2) 0.72938(14) 0.69533(8) 0.0187(4) Uani d . . . 1 . .
C C26 0.7784(2) 0.73091(17) 0.75853(9) 0.0273(4) Uani d . . . 1 . .
H H17 0.73989 0.798388 0.768944 0.041 Uiso calc U . R 1 . .
H H18 0.869016 0.715089 0.782138 0.041 Uiso calc U . R 1 . .
H H19 0.69827 0.680241 0.765842 0.041 Uiso calc U . R 1 . .
C C27 0.8055(2) 0.81323(15) 0.66273(10) 0.0273(4) Uani d . . . 1 . .
H H20 0.767321 0.873928 0.679693 0.033 Uiso calc U . R 1 . .
H H21 0.832757 0.811901 0.622693 0.033 Uiso calc U . R 1 . .
C C28 0.83473(18) 0.56217(12) 0.52612(7) 0.0127(3) Uani d . . . 1 . .
C C29 0.94104(19) 0.50575(12) 0.56851(7) 0.0125(3) Uani d . . . 1 . .
C C30 0.8650(2) 0.52689(14) 0.46396(7) 0.0170(3) Uani d . . . 1 . .
H H27 0.79293 0.560487 0.437456 0.025 Uiso calc U . R 1 . .
H H28 0.851042 0.453225 0.461558 0.025 Uiso calc U . R 1 . .
H H26 0.970477 0.54428 0.4529 0.025 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O5 H39 . 0.8581 ?
O5 H40 . 0.8819 ?
O1 C20 . 1.220(2) ?
O2 C18 . 1.422(2) ?
O2 H37 . 0.75(3) ?
O3 C29 . 1.208(2) ?
O4 C28 . 1.433(2) ?
O4 H38 . 0.80(3) ?
C1 C2 . 1.504(2) ?
C1 H15 . 0.98 ?
C1 H1 . 0.98 ?
C1 H16 . 0.98 ?
C2 C22 . 1.339(3) ?
C2 C3 . 1.480(2) ?
C3 C21 . 1.347(2) ?
C3 C4 . 1.522(2) ?
C4 C24 . 1.570(2) ?
C4 C5 . 1.573(2) ?
C4 C17 . 1.598(2) ?
C5 C18 . 1.555(2) ?
C5 C6 . 1.557(2) ?
C5 H10 . 1.0 ?
C6 C7 . 1.513(2) ?
C6 C28 . 1.551(2) ?
C6 H29 . 1.0 ?
C7 C16 . 1.346(2) ?
C7 C8 . 1.526(2) ?
C8 C9 . 1.532(2) ?
C8 C12 . 1.539(2) ?
C8 H34 . 1.0 ?
C9 C11 . 1.374(4) ?
C9 C10 . 1.446(4) ?
C10 H2 . 0.98 ?
C10 H36 . 0.98 ?
C10 H35 . 0.98 ?
C11 H3 . 0.95 ?
C11 H4 . 0.95 ?
C12 C13 . 1.524(3) ?
C12 H33 . 0.99 ?
C12 H32 . 0.99 ?
C13 C14 . 1.528(3) ?
C13 H31 . 0.99 ?
C13 H5 . 0.99 ?
C14 C16 . 1.517(2) ?
C14 C15 . 1.530(2) ?
C14 H6 . 1.0 ?
C15 H7 . 0.98 ?
C15 H8 . 0.98 ?
C15 H9 . 0.98 ?
C16 C17 . 1.522(2) ?
C17 C29 . 1.521(2) ?
C17 H30 . 1.0 ?
C18 C20 . 1.526(2) ?
C18 C19 . 1.535(2) ?
C19 H13 . 0.98 ?
C19 H11 . 0.98 ?
C19 H12 . 0.98 ?
C20 C21 . 1.456(2) ?
C21 H14 . 0.95 ?
C22 C23 . 1.497(3) ?
C22 H25 . 0.95 ?
C23 C24 . 1.534(2) ?
C23 H24 . 0.99 ?
C23 H23 . 0.99 ?
C24 C25 . 1.525(2) ?
C24 H22 . 1.0 ?
C25 C27 . 1.342(3) ?
C25 C26 . 1.499(3) ?
C26 H17 . 0.98 ?
C26 H18 . 0.98 ?
C26 H19 . 0.98 ?
C27 H20 . 0.95 ?
C27 H21 . 0.95 ?
C28 C30 . 1.525(2) ?
C28 C29 . 1.536(2) ?
C30 H27 . 0.98 ?
C30 H28 . 0.98 ?
C30 H26 . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
H39 O5 H40 . . 106.2 ?
C18 O2 H37 . . 109.5 ?
C28 O4 H38 . . 109.5 ?
C2 C1 H15 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H15 C1 H1 . . 109.5 ?
C2 C1 H16 . . 109.5 ?
H15 C1 H16 . . 109.5 ?
H1 C1 H16 . . 109.5 ?
C22 C2 C3 . . 120.37(16) ?
C22 C2 C1 . . 120.77(17) ?
C3 C2 C1 . . 118.78(16) ?
C21 C3 C2 . . 120.87(16) ?
C21 C3 C4 . . 121.33(15) ?
C2 C3 C4 . . 117.34(14) ?
C3 C4 C24 . . 109.62(13) ?
C3 C4 C5 . . 116.80(13) ?
C24 C4 C5 . . 110.82(13) ?
C3 C4 C17 . . 104.34(13) ?
C24 C4 C17 . . 108.62(13) ?
C5 C4 C17 . . 106.13(13) ?
C18 C5 C6 . . 111.46(13) ?
C18 C5 C4 . . 114.63(13) ?
C6 C5 C4 . . 110.34(13) ?
C18 C5 H10 . . 106.6 ?
C6 C5 H10 . . 106.6 ?
C4 C5 H10 . . 106.6 ?
C7 C6 C28 . . 108.73(13) ?
C7 C6 C5 . . 108.40(13) ?
C28 C6 C5 . . 108.79(13) ?
C7 C6 H29 . . 110.3 ?
C28 C6 H29 . . 110.3 ?
C5 C6 H29 . . 110.3 ?
C16 C7 C6 . . 113.69(14) ?
C16 C7 C8 . . 123.79(15) ?
C6 C7 C8 . . 122.39(14) ?
C7 C8 C9 . . 113.30(14) ?
C7 C8 C12 . . 110.37(14) ?
C9 C8 C12 . . 111.93(15) ?
C7 C8 H34 . . 107.0 ?
C9 C8 H34 . . 107.0 ?
C12 C8 H34 . . 107.0 ?
C11 C9 C10 . . 121.9(2) ?
C11 C9 C8 . . 118.7(2) ?
C10 C9 C8 . . 119.35(19) ?
C9 C10 H2 . . 109.5 ?
C9 C10 H36 . . 109.5 ?
H2 C10 H36 . . 109.5 ?
C9 C10 H35 . . 109.5 ?
H2 C10 H35 . . 109.5 ?
H36 C10 H35 . . 109.5 ?
C9 C11 H3 . . 120.0 ?
C9 C11 H4 . . 120.0 ?
H3 C11 H4 . . 120.0 ?
C13 C12 C8 . . 110.82(15) ?
C13 C12 H33 . . 109.5 ?
C8 C12 H33 . . 109.5 ?
C13 C12 H32 . . 109.5 ?
C8 C12 H32 . . 109.5 ?
H33 C12 H32 . . 108.1 ?
C12 C13 C14 . . 110.78(15) ?
C12 C13 H31 . . 109.5 ?
C14 C13 H31 . . 109.5 ?
C12 C13 H5 . . 109.5 ?
C14 C13 H5 . . 109.5 ?
H31 C13 H5 . . 108.1 ?
C16 C14 C13 . . 109.35(14) ?
C16 C14 C15 . . 115.41(15) ?
C13 C14 C15 . . 109.74(15) ?
C16 C14 H6 . . 107.3 ?
C13 C14 H6 . . 107.3 ?
C15 C14 H6 . . 107.3 ?
C14 C15 H7 . . 109.5 ?
C14 C15 H8 . . 109.5 ?
H7 C15 H8 . . 109.5 ?
C14 C15 H9 . . 109.5 ?
H7 C15 H9 . . 109.5 ?
H8 C15 H9 . . 109.5 ?
C7 C16 C14 . . 123.65(15) ?
C7 C16 C17 . . 113.69(14) ?
C14 C16 C17 . . 122.61(15) ?
C29 C17 C16 . . 105.85(13) ?
C29 C17 C4 . . 107.08(13) ?
C16 C17 C4 . . 110.62(13) ?
C29 C17 H30 . . 111.0 ?
C16 C17 H30 . . 111.0 ?
C4 C17 H30 . . 111.0 ?
O2 C18 C20 . . 108.12(14) ?
O2 C18 C19 . . 108.06(14) ?
C20 C18 C19 . . 107.50(14) ?
O2 C18 C5 . . 110.55(13) ?
C20 C18 C5 . . 112.30(13) ?
C19 C18 C5 . . 110.17(14) ?
C18 C19 H13 . . 109.5 ?
C18 C19 H11 . . 109.5 ?
H13 C19 H11 . . 109.5 ?
C18 C19 H12 . . 109.5 ?
H13 C19 H12 . . 109.5 ?
H11 C19 H12 . . 109.5 ?
O1 C20 C21 . . 123.57(16) ?
O1 C20 C18 . . 119.86(16) ?
C21 C20 C18 . . 116.33(15) ?
C3 C21 C20 . . 121.77(16) ?
C3 C21 H14 . . 119.1 ?
C20 C21 H14 . . 119.1 ?
C2 C22 C23 . . 124.60(16) ?
C2 C22 H25 . . 117.7 ?
C23 C22 H25 . . 117.7 ?
C22 C23 C24 . . 113.56(14) ?
C22 C23 H24 . . 108.9 ?
C24 C23 H24 . . 108.9 ?
C22 C23 H23 . . 108.9 ?
C24 C23 H23 . . 108.9 ?
H24 C23 H23 . . 107.7 ?
C25 C24 C23 . . 112.06(14) ?
C25 C24 C4 . . 114.28(13) ?
C23 C24 C4 . . 110.05(14) ?
C25 C24 H22 . . 106.7 ?
C23 C24 H22 . . 106.7 ?
C4 C24 H22 . . 106.7 ?
C27 C25 C26 . . 120.30(18) ?
C27 C25 C24 . . 119.11(17) ?
C26 C25 C24 . . 120.52(17) ?
C25 C26 H17 . . 109.5 ?
C25 C26 H18 . . 109.5 ?
H17 C26 H18 . . 109.5 ?
C25 C26 H19 . . 109.5 ?
H17 C26 H19 . . 109.5 ?
H18 C26 H19 . . 109.5 ?
C25 C27 H20 . . 120.0 ?
C25 C27 H21 . . 120.0 ?
H20 C27 H21 . . 120.0 ?
O4 C28 C30 . . 108.83(13) ?
O4 C28 C29 . . 106.24(13) ?
C30 C28 C29 . . 110.00(14) ?
O4 C28 C6 . . 111.54(13) ?
C30 C28 C6 . . 113.70(14) ?
C29 C28 C6 . . 106.24(13) ?
O3 C29 C17 . . 124.49(15) ?
O3 C29 C28 . . 122.61(15) ?
C17 C29 C28 . . 112.90(13) ?
C28 C30 H27 . . 109.5 ?
C28 C30 H28 . . 109.5 ?
H27 C30 H28 . . 109.5 ?
C28 C30 H26 . . 109.5 ?
H27 C30 H26 . . 109.5 ?
H28 C30 H26 . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C22 C2 C3 C21 . . . . -174.83(18) ?
C1 C2 C3 C21 . . . . 2.0(3) ?
C22 C2 C3 C4 . . . . 12.9(2) ?
C1 C2 C3 C4 . . . . -170.30(16) ?
C21 C3 C4 C24 . . . . 146.34(16) ?
C2 C3 C4 C24 . . . . -41.4(2) ?
C21 C3 C4 C5 . . . . 19.3(2) ?
C2 C3 C4 C5 . . . . -168.44(14) ?
C21 C3 C4 C17 . . . . -97.50(18) ?
C2 C3 C4 C17 . . . . 74.78(17) ?
C3 C4 C5 C18 . . . . 3.2(2) ?
C24 C4 C5 C18 . . . . -123.25(15) ?
C17 C4 C5 C18 . . . . 119.01(15) ?
C3 C4 C5 C6 . . . . -123.58(15) ?
C24 C4 C5 C6 . . . . 109.95(15) ?
C17 C4 C5 C6 . . . . -7.80(16) ?
C18 C5 C6 C7 . . . . -67.63(17) ?
C4 C5 C6 C7 . . . . 60.92(16) ?
C18 C5 C6 C28 . . . . 174.30(13) ?
C4 C5 C6 C28 . . . . -57.15(17) ?
C28 C6 C7 C16 . . . . 61.84(18) ?
C5 C6 C7 C16 . . . . -56.27(18) ?
C28 C6 C7 C8 . . . . -122.19(16) ?
C5 C6 C7 C8 . . . . 119.70(16) ?
C16 C7 C8 C9 . . . . -140.47(17) ?
C6 C7 C8 C9 . . . . 44.0(2) ?
C16 C7 C8 C12 . . . . -14.1(2) ?
C6 C7 C8 C12 . . . . 170.38(15) ?
C7 C8 C9 C11 . . . . -96.5(2) ?
C12 C8 C9 C11 . . . . 137.90(19) ?
C7 C8 C9 C10 . . . . 86.0(2) ?
C12 C8 C9 C10 . . . . -39.6(2) ?
C7 C8 C12 C13 . . . . 44.1(2) ?
C9 C8 C12 C13 . . . . 171.31(15) ?
C8 C12 C13 C14 . . . . -65.2(2) ?
C12 C13 C14 C16 . . . . 50.5(2) ?
C12 C13 C14 C15 . . . . 178.04(15) ?
C6 C7 C16 C14 . . . . 178.21(15) ?
C8 C7 C16 C14 . . . . 2.3(3) ?
C6 C7 C16 C17 . . . . -4.3(2) ?
C8 C7 C16 C17 . . . . 179.76(15) ?
C13 C14 C16 C7 . . . . -20.3(2) ?
C15 C14 C16 C7 . . . . -144.57(18) ?
C13 C14 C16 C17 . . . . 162.47(16) ?
C15 C14 C16 C17 . . . . 38.2(2) ?
C7 C16 C17 C29 . . . . -55.09(18) ?
C14 C16 C17 C29 . . . . 122.39(16) ?
C7 C16 C17 C4 . . . . 60.57(18) ?
C14 C16 C17 C4 . . . . -121.95(16) ?
C3 C4 C17 C29 . . . . -171.14(13) ?
C24 C4 C17 C29 . . . . -54.28(16) ?
C5 C4 C17 C29 . . . . 64.92(15) ?
C3 C4 C17 C16 . . . . 73.98(16) ?
C24 C4 C17 C16 . . . . -169.16(13) ?
C5 C4 C17 C16 . . . . -49.96(16) ?
C6 C5 C18 O2 . . . . -28.57(19) ?
C4 C5 C18 O2 . . . . -154.79(13) ?
C6 C5 C18 C20 . . . . 92.28(16) ?
C4 C5 C18 C20 . . . . -33.94(19) ?
C6 C5 C18 C19 . . . . -147.93(14) ?
C4 C5 C18 C19 . . . . 85.85(17) ?
O2 C18 C20 O1 . . . . -16.2(2) ?
C19 C18 C20 O1 . . . . 100.27(18) ?
C5 C18 C20 O1 . . . . -138.40(17) ?
O2 C18 C20 C21 . . . . 169.27(14) ?
C19 C18 C20 C21 . . . . -74.30(18) ?
C5 C18 C20 C21 . . . . 47.0(2) ?
C2 C3 C21 C20 . . . . -179.68(16) ?
C4 C3 C21 C20 . . . . -7.7(3) ?
O1 C20 C21 C3 . . . . 158.82(18) ?
C18 C20 C21 C3 . . . . -26.8(2) ?
C3 C2 C22 C23 . . . . 1.3(3) ?
C1 C2 C22 C23 . . . . -175.50(18) ?
C2 C22 C23 C24 . . . . 15.6(3) ?
C22 C23 C24 C25 . . . . 84.46(19) ?
C22 C23 C24 C4 . . . . -43.9(2) ?
C3 C4 C24 C25 . . . . -70.94(18) ?
C5 C4 C24 C25 . . . . 59.41(18) ?
C17 C4 C24 C25 . . . . 175.63(14) ?
C3 C4 C24 C23 . . . . 56.15(18) ?
C5 C4 C24 C23 . . . . -173.50(13) ?
C17 C4 C24 C23 . . . . -57.28(17) ?
C23 C24 C25 C27 . . . . 130.43(18) ?
C4 C24 C25 C27 . . . . -103.52(19) ?
C23 C24 C25 C26 . . . . -46.6(2) ?
C4 C24 C25 C26 . . . . 79.4(2) ?
C7 C6 C28 O4 . . . . -167.86(13) ?
C5 C6 C28 O4 . . . . -49.99(17) ?
C7 C6 C28 C30 . . . . 68.63(17) ?
C5 C6 C28 C30 . . . . -173.51(13) ?
C7 C6 C28 C29 . . . . -52.50(16) ?
C5 C6 C28 C29 . . . . 65.36(16) ?
C16 C17 C29 O3 . . . . -119.65(18) ?
C4 C17 C29 O3 . . . . 122.31(17) ?
C16 C17 C29 C28 . . . . 59.75(17) ?
C4 C17 C29 C28 . . . . -58.29(17) ?
O4 C28 C29 O3 . . . . -68.0(2) ?
C30 C28 C29 O3 . . . . 49.6(2) ?
C6 C28 C29 O3 . . . . 173.10(16) ?
O4 C28 C29 C17 . . . . 112.58(15) ?
C30 C28 C29 C17 . . . . -129.79(15) ?
C6 C28 C29 C17 . . . . -6.31(18) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O5 H39 O2 2_566 0.86 1.96 2.8183(18) 174.9 ?
O5 H40 O4 2_466 0.88 1.97 2.8422(18) 171.4 ?
O2 H37 O1 . 0.75 2.16 2.6144(18) 119.5 ?
O2 H37 O3 1_455 0.75 2.20 2.8370(18) 143.3 ?
O4 H38 O5 . 0.80 1.88 2.6768(19) 171.7 ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_she156_0m
_database_code_depnum_ccdc_archive 'CCDC 2212942'
loop_
_audit_author_name
_audit_author_address
'Xiao-Nian Li'
;Kunming Institute of Botany
China
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-11-28 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         'C30 H40 O4'
_chemical_formula_sum            'C30 H40 O4'
_chemical_formula_weight         464.62

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                   8.6842(2)
_cell_length_b                   15.4286(3)
_cell_length_c                   19.2929(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2584.96(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      68.99

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   0.3309
_exptl_transmission_factor_max   0.5854
_exptl_crystal_size_max          0.720
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.380
_exptl_absorpt_coefficient_mu    0.610
_shelx_estimated_absorpt_T_min   0.668
_shelx_estimated_absorpt_T_max   0.801
_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      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14778
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.668
_diffrn_reflns_theta_max         69.407
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             4472
_reflns_number_gt                4448
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_max     0.871
_reflns_Friedel_fraction_full    0.905

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+1.0723P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 1795 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4472
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4192(2) 0.21818(11) 0.75500(9) 0.0246(4) Uani 1 1 d . . . . .
H1 H 0.3808 0.1708 0.7679 0.037 Uiso 1 1 calc R U . . .
O2 O 0.6805(2) 0.13858(11) 0.83356(10) 0.0256(4) Uani 1 1 d . . . . .
O3 O 0.7634(2) 0.57571(11) 0.72314(10) 0.0288(4) Uani 1 1 d . . . . .
O4 O 0.4815(2) 0.49770(11) 0.72573(9) 0.0238(4) Uani 1 1 d . . . . .
H4 H 0.4550 0.5399 0.7010 0.036 Uiso 1 1 calc R U . . .
C1 C 1.0424(3) 0.22817(17) 0.65332(14) 0.0259(6) Uani 1 1 d . . . . .
H1A H 1.0377 0.2422 0.6033 0.031 Uiso 1 1 calc R U . . .
H1B H 1.1367 0.1936 0.6612 0.031 Uiso 1 1 calc R U . . .
C2 C 0.9024(3) 0.17278(16) 0.67202(13) 0.0233(5) Uani 1 1 d . . . . .
H2A H 0.9186 0.1471 0.7185 0.028 Uiso 1 1 calc R U . . .
H2B H 0.8939 0.1246 0.6383 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7498(3) 0.22418(16) 0.67232(13) 0.0210(5) Uani 1 1 d . . . . .
H3 H 0.6724 0.1857 0.6953 0.025 Uiso 1 1 calc R U . . .
C4 C 0.7615(3) 0.30746(15) 0.71914(12) 0.0171(5) Uani 1 1 d . . . . .
C5 C 0.6033(3) 0.35787(15) 0.71980(12) 0.0175(5) Uani 1 1 d . . . . .
H5 H 0.5330 0.3255 0.6880 0.021 Uiso 1 1 calc R U . . .
C6 C 0.5300(3) 0.35201(15) 0.79339(12) 0.0177(5) Uani 1 1 d . . . . .
H6 H 0.4306 0.3847 0.7946 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6429(3) 0.39080(15) 0.84471(11) 0.0189(5) Uani 1 1 d . . . . .
C8 C 0.6065(3) 0.47309(16) 0.88399(13) 0.0229(5) Uani 1 1 d . . . . .
H8 H 0.5668 0.5151 0.8488 0.028 Uiso 1 1 calc R U . . .
C9 C 0.4769(4) 0.46036(18) 0.93605(16) 0.0344(7) Uani 1 1 d . . . . .
C10 C 0.3337(4) 0.4777(2) 0.9181(2) 0.0554(10) Uani 1 1 d . . . . .
H10A H 0.2526 0.4699 0.9505 0.066 Uiso 1 1 calc R U . . .
H10B H 0.3116 0.4981 0.8727 0.066 Uiso 1 1 calc R U . . .
C11 C 0.7710(4) 0.2854(3) 0.54942(16) 0.0654(14) Uani 1 1 d . . . . .
H11A H 0.7304 0.2914 0.5040 0.078 Uiso 1 1 calc R U . . .
H11B H 0.8675 0.3108 0.5607 0.078 Uiso 1 1 calc R U . . .
C12 C 0.6897(3) 0.23976(19) 0.59915(14) 0.0298(6) Uani 1 1 d . . . . .
C13 C 0.7907(3) 0.27450(15) 0.79675(12) 0.0186(5) Uani 1 1 d . . . . .
H13 H 0.8930 0.2452 0.8009 0.022 Uiso 1 1 calc R U . . .
C14 C 0.7793(3) 0.35044(15) 0.84605(12) 0.0185(5) Uani 1 1 d . . . . .
C15 C 0.5176(5) 0.4279(2) 1.00754(17) 0.0489(9) Uani 1 1 d . . . . .
H15A H 0.4231 0.4178 1.0340 0.073 Uiso 1 1 calc R U . . .
H15B H 0.5809 0.4713 1.0314 0.073 Uiso 1 1 calc R U . . .
H15C H 0.5754 0.3736 1.0036 0.073 Uiso 1 1 calc R U . . .
C16 C 0.7569(4) 0.51242(18) 0.91219(16) 0.0334(6) Uani 1 1 d . . . . .
H16A H 0.8085 0.5444 0.8743 0.040 Uiso 1 1 calc R U . . .
H16B H 0.7309 0.5549 0.9489 0.040 Uiso 1 1 calc R U . . .
C17 C 0.8691(4) 0.4468(2) 0.94174(15) 0.0341(7) Uani 1 1 d . . . . .
H17A H 0.8214 0.4183 0.9824 0.041 Uiso 1 1 calc R U . . .
H17B H 0.9624 0.4776 0.9580 0.041 Uiso 1 1 calc R U . . .
C18 C 0.9161(3) 0.37765(16) 0.88942(13) 0.0226(5) Uani 1 1 d . . . . .
H18 H 0.9964 0.4025 0.8580 0.027 Uiso 1 1 calc R U . . .
C19 C 0.9860(4) 0.3005(2) 0.92848(14) 0.0342(7) Uani 1 1 d . . . . .
H19A H 1.0236 0.2576 0.8951 0.051 Uiso 1 1 calc R U . . .
H19B H 0.9072 0.2741 0.9581 0.051 Uiso 1 1 calc R U . . .
H19C H 1.0718 0.3207 0.9573 0.051 Uiso 1 1 calc R U . . .
C20 C 0.5021(3) 0.25625(15) 0.81122(12) 0.0204(5) Uani 1 1 d . . . . .
C21 C 0.6618(3) 0.21366(16) 0.81608(12) 0.0197(5) Uani 1 1 d . . . . .
C22 C 0.4143(3) 0.24502(17) 0.87891(14) 0.0272(6) Uani 1 1 d . . . . .
H22A H 0.4020 0.1831 0.8888 0.041 Uiso 1 1 calc R U . . .
H22B H 0.3127 0.2721 0.8748 0.041 Uiso 1 1 calc R U . . .
H22C H 0.4718 0.2726 0.9167 0.041 Uiso 1 1 calc R U . . .
C23 C 0.6054(3) 0.45339(16) 0.69351(12) 0.0198(5) Uani 1 1 d . . . . .
C24 C 0.7578(3) 0.49829(16) 0.70902(12) 0.0207(5) Uani 1 1 d . . . . .
C25 C 0.8982(3) 0.44798(16) 0.69955(12) 0.0198(5) Uani 1 1 d . . . . .
H25 H 0.9918 0.4783 0.6917 0.024 Uiso 1 1 calc R U . . .
C26 C 0.9024(3) 0.36081(16) 0.70130(12) 0.0180(5) Uani 1 1 d . . . . .
C27 C 1.0551(3) 0.31277(17) 0.69437(14) 0.0225(5) Uani 1 1 d . . . . .
H27 H 1.0879 0.2966 0.7424 0.027 Uiso 1 1 calc R U . . .
C28 C 1.1845(3) 0.36769(18) 0.66367(16) 0.0305(6) Uani 1 1 d . . . . .
H28A H 1.1524 0.3902 0.6184 0.046 Uiso 1 1 calc R U . . .
H28B H 1.2769 0.3319 0.6580 0.046 Uiso 1 1 calc R U . . .
H28C H 1.2072 0.4162 0.6949 0.046 Uiso 1 1 calc R U . . .
C29 C 0.5847(3) 0.45918(19) 0.61460(13) 0.0293(6) Uani 1 1 d . . . . .
H29A H 0.5855 0.5201 0.6003 0.044 Uiso 1 1 calc R U . . .
H29B H 0.4863 0.4327 0.6015 0.044 Uiso 1 1 calc R U . . .
H29C H 0.6691 0.4284 0.5916 0.044 Uiso 1 1 calc R U . . .
C30 C 0.5460(4) 0.2019(2) 0.5826(2) 0.0472(9) Uani 1 1 d . . . . .
H30A H 0.5599 0.1398 0.5740 0.071 Uiso 1 1 calc R U . . .
H30B H 0.5041 0.2296 0.5409 0.071 Uiso 1 1 calc R U . . .
H30C H 0.4745 0.2101 0.6213 0.071 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 C20 1.428(3) . ?
O1 H1 0.8400 . ?
O2 C21 1.217(3) . ?
O3 C24 1.226(3) . ?
O4 C23 1.418(3) . ?
O4 H4 0.8400 . ?
C1 C2 1.529(4) . ?
C1 C27 1.531(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.545(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C12 1.524(4) . ?
C3 C4 1.574(3) . ?
C3 H3 1.0000 . ?
C4 C26 1.514(3) . ?
C4 C5 1.578(3) . ?
C4 C13 1.602(3) . ?
C5 C23 1.559(3) . ?
C5 C6 1.559(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.516(3) . ?
C6 C20 1.536(3) . ?
C6 H6 1.0000 . ?
C7 C14 1.339(4) . ?
C7 C8 1.512(3) . ?
C8 C9 1.521(4) . ?
C8 C16 1.539(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.319(5) . ?
C9 C15 1.509(5) . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C11 C12 1.384(5) . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
C12 C30 1.415(4) . ?
C13 C21 1.508(3) . ?
C13 C14 1.512(3) . ?
C13 H13 1.0000 . ?
C14 C18 1.512(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.516(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.525(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.534(4) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C22 1.522(3) . ?
C20 C21 1.537(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.523(3) . ?
C23 C29 1.536(3) . ?
C24 C25 1.457(4) . ?
C25 C26 1.346(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.525(3) . ?
C27 C28 1.527(4) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 H1 109.5 . . ?
C23 O4 H4 109.5 . . ?
C2 C1 C27 114.3(2) . . ?
C2 C1 H1A 108.7 . . ?
C27 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C27 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 C3 113.3(2) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C12 C3 C2 111.8(2) . . ?
C12 C3 C4 115.1(2) . . ?
C2 C3 C4 111.5(2) . . ?
C12 C3 H3 105.9 . . ?
C2 C3 H3 105.9 . . ?
C4 C3 H3 105.9 . . ?
C26 C4 C3 111.45(19) . . ?
C26 C4 C5 115.92(19) . . ?
C3 C4 C5 110.53(19) . . ?
C26 C4 C13 104.89(19) . . ?
C3 C4 C13 106.71(18) . . ?
C5 C4 C13 106.66(18) . . ?
C23 C5 C6 110.85(19) . . ?
C23 C5 C4 116.94(19) . . ?
C6 C5 C4 109.53(18) . . ?
C23 C5 H5 106.3 . . ?
C6 C5 H5 106.3 . . ?
C4 C5 H5 106.3 . . ?
C7 C6 C20 109.59(19) . . ?
C7 C6 C5 107.93(19) . . ?
C20 C6 C5 108.91(19) . . ?
C7 C6 H6 110.1 . . ?
C20 C6 H6 110.1 . . ?
C5 C6 H6 110.1 . . ?
C14 C7 C8 124.4(2) . . ?
C14 C7 C6 113.7(2) . . ?
C8 C7 C6 121.6(2) . . ?
C7 C8 C9 112.1(2) . . ?
C7 C8 C16 109.3(2) . . ?
C9 C8 C16 116.4(2) . . ?
C7 C8 H8 106.1 . . ?
C9 C8 H8 106.1 . . ?
C16 C8 H8 106.1 . . ?
C10 C9 C15 121.9(3) . . ?
C10 C9 C8 119.9(3) . . ?
C15 C9 C8 118.2(3) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C12 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C11 C12 C30 120.3(3) . . ?
C11 C12 C3 123.2(3) . . ?
C30 C12 C3 116.5(3) . . ?
C21 C13 C14 106.16(19) . . ?
C21 C13 C4 108.14(19) . . ?
C14 C13 C4 109.37(18) . . ?
C21 C13 H13 111.0 . . ?
C14 C13 H13 111.0 . . ?
C4 C13 H13 111.0 . . ?
C7 C14 C18 125.2(2) . . ?
C7 C14 C13 113.9(2) . . ?
C18 C14 C13 120.8(2) . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C8 114.5(2) . . ?
C17 C16 H16A 108.6 . . ?
C8 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C8 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C18 113.0(2) . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C14 C18 C17 110.5(2) . . ?
C14 C18 C19 111.6(2) . . ?
C17 C18 C19 108.9(2) . . ?
C14 C18 H18 108.6 . . ?
C17 C18 H18 108.6 . . ?
C19 C18 H18 108.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 C22 110.6(2) . . ?
O1 C20 C6 107.76(18) . . ?
C22 C20 C6 112.4(2) . . ?
O1 C20 C21 109.00(19) . . ?
C22 C20 C21 110.5(2) . . ?
C6 C20 C21 106.4(2) . . ?
O2 C21 C13 124.2(2) . . ?
O2 C21 C20 123.0(2) . . ?
C13 C21 C20 112.9(2) . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 C24 110.7(2) . . ?
O4 C23 C29 108.5(2) . . ?
C24 C23 C29 105.7(2) . . ?
O4 C23 C5 107.72(19) . . ?
C24 C23 C5 112.11(19) . . ?
C29 C23 C5 112.1(2) . . ?
O3 C24 C25 120.9(2) . . ?
O3 C24 C23 121.4(2) . . ?
C25 C24 C23 117.4(2) . . ?
C26 C25 C24 123.5(2) . . ?
C26 C25 H25 118.3 . . ?
C24 C25 H25 118.3 . . ?
C25 C26 C4 121.8(2) . . ?
C25 C26 C27 120.5(2) . . ?
C4 C26 C27 117.3(2) . . ?
C26 C27 C28 113.8(2) . . ?
C26 C27 C1 113.4(2) . . ?
C28 C27 C1 109.0(2) . . ?
C26 C27 H27 106.7 . . ?
C28 C27 H27 106.7 . . ?
C1 C27 H27 106.7 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C29 H29A 109.5 . . ?
C23 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C23 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C12 C30 H30A 109.5 . . ?
C12 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C12 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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
C27 C1 C2 C3 49.7(3) . . . . ?
C1 C2 C3 C12 77.7(3) . . . . ?
C1 C2 C3 C4 -52.8(3) . . . . ?
C12 C3 C4 C26 -78.0(3) . . . . ?
C2 C3 C4 C26 50.7(3) . . . . ?
C12 C3 C4 C5 52.4(3) . . . . ?
C2 C3 C4 C5 -178.89(19) . . . . ?
C12 C3 C4 C13 168.0(2) . . . . ?
C2 C3 C4 C13 -63.3(2) . . . . ?
C26 C4 C5 C23 7.3(3) . . . . ?
C3 C4 C5 C23 -120.8(2) . . . . ?
C13 C4 C5 C23 123.6(2) . . . . ?
C26 C4 C5 C6 -119.9(2) . . . . ?
C3 C4 C5 C6 112.1(2) . . . . ?
C13 C4 C5 C6 -3.6(2) . . . . ?
C23 C5 C6 C7 -71.8(2) . . . . ?
C4 C5 C6 C7 58.7(2) . . . . ?
C23 C5 C6 C20 169.30(19) . . . . ?
C4 C5 C6 C20 -60.2(2) . . . . ?
C20 C6 C7 C14 58.8(3) . . . . ?
C5 C6 C7 C14 -59.6(3) . . . . ?
C20 C6 C7 C8 -127.4(2) . . . . ?
C5 C6 C7 C8 114.2(2) . . . . ?
C14 C7 C8 C9 -118.9(3) . . . . ?
C6 C7 C8 C9 68.0(3) . . . . ?
C14 C7 C8 C16 11.8(3) . . . . ?
C6 C7 C8 C16 -161.3(2) . . . . ?
C7 C8 C9 C10 -93.4(3) . . . . ?
C16 C8 C9 C10 139.6(3) . . . . ?
C7 C8 C9 C15 86.6(3) . . . . ?
C16 C8 C9 C15 -40.3(4) . . . . ?
C2 C3 C12 C11 -60.5(4) . . . . ?
C4 C3 C12 C11 68.0(4) . . . . ?
C2 C3 C12 C30 117.1(3) . . . . ?
C4 C3 C12 C30 -114.4(3) . . . . ?
C26 C4 C13 C21 -174.74(19) . . . . ?
C3 C4 C13 C21 -56.4(2) . . . . ?
C5 C4 C13 C21 61.8(2) . . . . ?
C26 C4 C13 C14 70.1(2) . . . . ?
C3 C4 C13 C14 -171.58(19) . . . . ?
C5 C4 C13 C14 -53.4(2) . . . . ?
C8 C7 C14 C18 3.2(4) . . . . ?
C6 C7 C14 C18 176.8(2) . . . . ?
C8 C7 C14 C13 -174.2(2) . . . . ?
C6 C7 C14 C13 -0.6(3) . . . . ?
C21 C13 C14 C7 -57.2(3) . . . . ?
C4 C13 C14 C7 59.3(3) . . . . ?
C21 C13 C14 C18 125.3(2) . . . . ?
C4 C13 C14 C18 -118.3(2) . . . . ?
C7 C8 C16 C17 -41.4(3) . . . . ?
C9 C8 C16 C17 86.9(3) . . . . ?
C8 C16 C17 C18 57.9(3) . . . . ?
C7 C14 C18 C17 10.7(3) . . . . ?
C13 C14 C18 C17 -172.0(2) . . . . ?
C7 C14 C18 C19 132.0(3) . . . . ?
C13 C14 C18 C19 -50.7(3) . . . . ?
C16 C17 C18 C14 -39.6(3) . . . . ?
C16 C17 C18 C19 -162.5(2) . . . . ?
C7 C6 C20 O1 -169.38(19) . . . . ?
C5 C6 C20 O1 -51.5(3) . . . . ?
C7 C6 C20 C22 68.5(3) . . . . ?
C5 C6 C20 C22 -173.6(2) . . . . ?
C7 C6 C20 C21 -52.6(2) . . . . ?
C5 C6 C20 C21 65.3(2) . . . . ?
C14 C13 C21 O2 -121.5(3) . . . . ?
C4 C13 C21 O2 121.2(2) . . . . ?
C14 C13 C21 C20 58.7(2) . . . . ?
C4 C13 C21 C20 -58.6(2) . . . . ?
O1 C20 C21 O2 -68.5(3) . . . . ?
C22 C20 C21 O2 53.3(3) . . . . ?
C6 C20 C21 O2 175.5(2) . . . . ?
O1 C20 C21 C13 111.3(2) . . . . ?
C22 C20 C21 C13 -126.9(2) . . . . ?
C6 C20 C21 C13 -4.7(3) . . . . ?
C6 C5 C23 O4 -27.5(2) . . . . ?
C4 C5 C23 O4 -154.02(19) . . . . ?
C6 C5 C23 C24 94.5(2) . . . . ?
C4 C5 C23 C24 -32.0(3) . . . . ?
C6 C5 C23 C29 -146.8(2) . . . . ?
C4 C5 C23 C29 86.7(3) . . . . ?
O4 C23 C24 O3 -25.4(3) . . . . ?
C29 C23 C24 O3 91.9(3) . . . . ?
C5 C23 C24 O3 -145.7(2) . . . . ?
O4 C23 C24 C25 160.7(2) . . . . ?
C29 C23 C24 C25 -82.0(3) . . . . ?
C5 C23 C24 C25 40.4(3) . . . . ?
O3 C24 C25 C26 162.8(2) . . . . ?
C23 C24 C25 C26 -23.3(3) . . . . ?
C24 C25 C26 C4 -5.0(4) . . . . ?
C24 C25 C26 C27 -177.1(2) . . . . ?
C3 C4 C26 C25 140.1(2) . . . . ?
C5 C4 C26 C25 12.5(3) . . . . ?
C13 C4 C26 C25 -104.8(2) . . . . ?
C3 C4 C26 C27 -47.5(3) . . . . ?
C5 C4 C26 C27 -175.11(19) . . . . ?
C13 C4 C26 C27 67.6(2) . . . . ?
C25 C26 C27 C28 -18.1(3) . . . . ?
C4 C26 C27 C28 169.4(2) . . . . ?
C25 C26 C27 C1 -143.5(2) . . . . ?
C4 C26 C27 C1 44.1(3) . . . . ?
C2 C1 C27 C26 -43.8(3) . . . . ?
C2 C1 C27 C28 -171.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O2 0.84 2.04 2.831(2) 157.6 3_656
O1 H1 O3 0.84 1.94 2.743(2) 160.3 3_646
O4 H4 O2 0.84 2.04 2.831(2) 157.6 3_656
O1 H1 O3 0.84 1.94 2.743(2) 160.3 3_646
O4 H4 O2 0.84 2.04 2.831(2) 157.6 3_656
O1 H1 O3 0.84 1.94 2.743(2) 160.3 3_646
O1 H1 O3 0.84 1.94 2.743(2) 160.3 3_646
O4 H4 O2 0.84 2.04 2.831(2) 157.6 3_656
O1 H1 O3 0.84 1.94 2.743(2) 160.3 3_646
O4 H4 O2 0.84 2.04 2.831(2) 157.6 3_656

_refine_diff_density_max         0.434
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_shp12
_database_code_depnum_ccdc_archive 'CCDC 2212943'
loop_
_audit_author_name
_audit_author_address
'Xiao-Nian Li'
;Kunming Institute of Botany
China
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C30 H34 O4'
_chemical_formula_sum            'C30 H34 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         458.57
_chemical_absolute_configuration ad

_chemical_melting_point          ?

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

_cell_length_a                   8.7330(5)
_cell_length_b                   9.9169(6)
_cell_length_c                   28.6719(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2483.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9322
_cell_measurement_theta_min      4.7183
_cell_measurement_theta_max      72.1319
_cell_measurement_temperature    101.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984

_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      101.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            26362
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         72.25
_diffrn_reflns_theta_full        72.25
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35

_refine_special_details          
;
;

_reflns_number_total             4890
_reflns_number_gt                4706
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0997
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_number_reflns         4890
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²+0.3720P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1959 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(6)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.27062(16) 0.65495(16) 0.71210(5) 0.0244(3) Uani d . . . 1 . .
H H33 0.19299 0.624857 0.725918 0.037 Uiso calc U . R 1 . .
O O2 0.02034(15) 0.52915(17) 0.68481(5) 0.0263(3) Uani d . . . 1 . .
C C1 0.0475(3) 0.3939(2) 0.51360(8) 0.0293(5) Uani d . . . 1 . .
H H1 0.053199 0.360234 0.481511 0.044 Uiso calc U . R 1 . .
H H16 -0.021516 0.471748 0.514826 0.044 Uiso calc U . R 1 . .
H H17 0.008425 0.322552 0.534042 0.044 Uiso calc U . R 1 . .
C C2 0.2046(2) 0.4356(2) 0.52960(7) 0.0233(4) Uani d . . . 1 . .
C C3 0.2234(2) 0.48064(19) 0.57820(7) 0.0199(4) Uani d . . . 1 . .
O O3 0.72572(16) 0.53805(16) 0.65090(5) 0.0272(3) Uani d . . . 1 . .
H H34 0.814066 0.52942 0.662092 0.041 Uiso calc U . R 1 . .
C C4 0.3866(2) 0.4950(2) 0.59627(6) 0.0186(4) Uani d . . . 1 . .
O O4 0.70665(17) 0.29160(19) 0.59436(6) 0.0336(4) Uani d . . . 1 . .
C C5 0.4389(2) 0.3425(2) 0.60361(6) 0.0199(4) Uani d . . . 1 . .
H H26 0.422105 0.288284 0.574642 0.024 Uiso calc U . R 1 . .
C C6 0.3522(2) 0.2826(2) 0.64448(7) 0.0208(4) Uani d . . . 1 . .
C C7 0.3749(2) 0.3505(2) 0.68655(7) 0.0208(4) Uani d . . . 1 . .
C C8 0.2980(2) 0.3095(2) 0.72718(7) 0.0253(4) Uani d . . . 1 . .
C C9 0.3081(3) 0.3802(2) 0.77310(8) 0.0321(5) Uani d . . . 1 . .
C C10 0.4506(3) 0.4122(3) 0.79363(8) 0.0336(5) Uani d . . . 1 . .
H H5 0.453989 0.45381 0.823457 0.04 Uiso calc U . R 1 . .
H H6 0.543071 0.392031 0.777624 0.04 Uiso calc U . R 1 . .
C C11 0.1682(3) 0.4090(3) 0.79615(10) 0.0441(6) Uani d . . . 1 . .
H H3 0.125841 0.325698 0.809227 0.066 Uiso calc U . R 1 . .
H H2 0.095342 0.447524 0.773821 0.066 Uiso calc U . R 1 . .
H H4 0.186712 0.473825 0.821341 0.066 Uiso calc U . R 1 . .
C C12 0.2004(3) 0.1980(2) 0.72306(8) 0.0303(5) Uani d . . . 1 . .
H H7 0.146929 0.167228 0.749888 0.036 Uiso calc U . R 1 . .
C C13 0.1795(2) 0.1314(2) 0.68133(9) 0.0298(5) Uani d . . . 1 . .
H H30 0.112932 0.055687 0.680235 0.036 Uiso calc U . R 1 . .
C C30 0.5643(3) 0.7985(2) 0.56982(7) 0.0278(4) Uani d . . . 1 . .
H H31 0.552114 0.892221 0.563965 0.033 Uiso calc U . R 1 . .
H H32 0.645129 0.767897 0.589299 0.033 Uiso calc U . R 1 . .
C C14 0.2535(2) 0.1726(2) 0.64076(7) 0.0248(4) Uani d . . . 1 . .
C C15 0.4060(2) 0.5682(2) 0.64442(6) 0.0179(4) Uani d . . . 1 . .
H H25 0.480137 0.64379 0.639522 0.022 Uiso calc U . R 1 . .
C C16 0.2563(2) 0.6313(2) 0.66356(6) 0.0202(4) Uani d . . . 1 . .
C C17 0.1181(2) 0.5426(2) 0.65425(7) 0.0209(4) Uani d . . . 1 . .
C C18 0.1017(2) 0.4913(2) 0.60708(7) 0.0219(4) Uani d . . . 1 . .
H H8 0.003403 0.464661 0.596294 0.026 Uiso calc U . R 1 . .
C C19 0.3248(3) 0.4345(2) 0.50023(7) 0.0265(4) Uani d . . . 1 . .
H H15 0.307637 0.403338 0.469338 0.032 Uiso calc U . R 1 . .
C C20 0.4834(3) 0.4790(2) 0.51263(7) 0.0262(4) Uani d . . . 1 . .
H H9 0.52416 0.535154 0.486932 0.031 Uiso calc U . R 1 . .
H H10 0.549623 0.3983 0.515331 0.031 Uiso calc U . R 1 . .
C C21 0.4933(2) 0.5598(2) 0.55839(7) 0.0222(4) Uani d . . . 1 . .
H H14 0.600594 0.549736 0.570035 0.027 Uiso calc U . R 1 . .
C C22 0.4675(2) 0.7096(2) 0.55059(7) 0.0239(4) Uani d . . . 1 . .
C C23 0.3384(3) 0.7554(2) 0.51957(8) 0.0294(4) Uani d . . . 1 . .
H H13 0.329587 0.853834 0.521076 0.044 Uiso calc U . R 1 . .
H H11 0.242417 0.714302 0.530093 0.044 Uiso calc U . R 1 . .
H H12 0.359304 0.72791 0.487364 0.044 Uiso calc U . R 1 . .
C C24 0.2207(2) 0.7671(2) 0.64039(7) 0.0252(4) Uani d . . . 1 . .
H H18 0.124117 0.802602 0.652751 0.038 Uiso calc U . R 1 . .
H H19 0.211541 0.754567 0.606597 0.038 Uiso calc U . R 1 . .
H H20 0.303533 0.830927 0.647003 0.038 Uiso calc U . R 1 . .
C C25 0.4788(2) 0.4712(2) 0.68093(6) 0.0195(4) Uani d . . . 1 . .
H H24 0.491586 0.518446 0.71149 0.023 Uiso calc U . R 1 . .
C C26 0.6360(2) 0.4226(2) 0.66252(7) 0.0217(4) Uani d . . . 1 . .
C C27 0.6068(2) 0.3439(2) 0.61712(7) 0.0231(4) Uani d . . . 1 . .
C C28 0.7195(2) 0.3318(2) 0.69715(7) 0.0274(4) Uani d . . . 1 . .
H H22 0.81512 0.299565 0.683152 0.041 Uiso calc U . R 1 . .
H H21 0.654405 0.25463 0.705006 0.041 Uiso calc U . R 1 . .
H H23 0.74268 0.382996 0.72553 0.041 Uiso calc U . R 1 . .
C C29 0.2243(3) 0.1013(2) 0.59524(8) 0.0319(5) Uani d . . . 1 . .
H H29 0.141424 0.035717 0.599316 0.048 Uiso calc U . R 1 . .
H H27 0.317567 0.054351 0.585336 0.048 Uiso calc U . R 1 . .
H H28 0.194953 0.167369 0.571458 0.048 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C16 . 1.417(2) ?
O1 H33 . 0.84 ?
O2 C17 . 1.231(3) ?
C1 C2 . 1.505(3) ?
C1 H1 . 0.98 ?
C1 H16 . 0.98 ?
C1 H17 . 0.98 ?
C2 C19 . 1.346(3) ?
C2 C3 . 1.473(3) ?
C3 C18 . 1.351(3) ?
C3 C4 . 1.523(3) ?
O3 C26 . 1.426(2) ?
O3 H34 . 0.84 ?
C4 C21 . 1.569(3) ?
C4 C15 . 1.569(3) ?
C4 C5 . 1.594(3) ?
O4 C27 . 1.206(3) ?
C5 C6 . 1.516(3) ?
C5 C27 . 1.517(3) ?
C5 H26 . 1.0 ?
C6 C14 . 1.395(3) ?
C6 C7 . 1.395(3) ?
C7 C8 . 1.405(3) ?
C7 C25 . 1.511(3) ?
C8 C12 . 1.401(3) ?
C8 C9 . 1.494(3) ?
C9 C10 . 1.413(4) ?
C9 C11 . 1.419(3) ?
C10 H5 . 0.95 ?
C10 H6 . 0.95 ?
C11 H3 . 0.98 ?
C11 H2 . 0.98 ?
C11 H4 . 0.98 ?
C12 C13 . 1.379(3) ?
C12 H7 . 0.95 ?
C13 C14 . 1.392(3) ?
C13 H30 . 0.95 ?
C30 C22 . 1.340(3) ?
C30 H31 . 0.95 ?
C30 H32 . 0.95 ?
C14 C29 . 1.506(3) ?
C15 C16 . 1.550(2) ?
C15 C25 . 1.557(3) ?
C15 H25 . 1.0 ?
C16 C17 . 1.517(3) ?
C16 C24 . 1.534(3) ?
C17 C18 . 1.452(3) ?
C18 H8 . 0.95 ?
C19 C20 . 1.497(3) ?
C19 H15 . 0.95 ?
C20 C21 . 1.540(3) ?
C20 H9 . 0.99 ?
C20 H10 . 0.99 ?
C21 C22 . 1.520(3) ?
C21 H14 . 1.0 ?
C22 C23 . 1.506(3) ?
C23 H13 . 0.98 ?
C23 H11 . 0.98 ?
C23 H12 . 0.98 ?
C24 H18 . 0.98 ?
C24 H19 . 0.98 ?
C24 H20 . 0.98 ?
C25 C26 . 1.548(3) ?
C25 H24 . 1.0 ?
C26 C28 . 1.526(3) ?
C26 C27 . 1.540(3) ?
C28 H22 . 0.98 ?
C28 H21 . 0.98 ?
C28 H23 . 0.98 ?
C29 H29 . 0.98 ?
C29 H27 . 0.98 ?
C29 H28 . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16 O1 H33 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
C2 C1 H16 . . 109.5 ?
H1 C1 H16 . . 109.5 ?
C2 C1 H17 . . 109.5 ?
H1 C1 H17 . . 109.5 ?
H16 C1 H17 . . 109.5 ?
C19 C2 C3 . . 120.50(18) ?
C19 C2 C1 . . 121.22(18) ?
C3 C2 C1 . . 118.28(18) ?
C18 C3 C2 . . 121.04(18) ?
C18 C3 C4 . . 121.34(17) ?
C2 C3 C4 . . 117.06(17) ?
C26 O3 H34 . . 109.5 ?
C3 C4 C21 . . 111.00(15) ?
C3 C4 C15 . . 116.35(15) ?
C21 C4 C15 . . 110.80(15) ?
C3 C4 C5 . . 102.97(15) ?
C21 C4 C5 . . 108.05(15) ?
C15 C4 C5 . . 107.00(15) ?
C6 C5 C27 . . 106.77(15) ?
C6 C5 C4 . . 109.30(15) ?
C27 C5 C4 . . 107.59(16) ?
C6 C5 H26 . . 111.0 ?
C27 C5 H26 . . 111.0 ?
C4 C5 H26 . . 111.0 ?
C14 C6 C7 . . 122.08(18) ?
C14 C6 C5 . . 123.75(18) ?
C7 C6 C5 . . 114.13(17) ?
C6 C7 C8 . . 120.63(19) ?
C6 C7 C25 . . 112.02(17) ?
C8 C7 C25 . . 127.23(19) ?
C12 C8 C7 . . 116.7(2) ?
C12 C8 C9 . . 118.74(19) ?
C7 C8 C9 . . 124.49(19) ?
C10 C9 C11 . . 121.3(2) ?
C10 C9 C8 . . 121.7(2) ?
C11 C9 C8 . . 117.0(2) ?
C9 C10 H5 . . 120.0 ?
C9 C10 H6 . . 120.0 ?
H5 C10 H6 . . 120.0 ?
C9 C11 H3 . . 109.5 ?
C9 C11 H2 . . 109.5 ?
H3 C11 H2 . . 109.5 ?
C9 C11 H4 . . 109.5 ?
H3 C11 H4 . . 109.5 ?
H2 C11 H4 . . 109.5 ?
C13 C12 C8 . . 122.1(2) ?
C13 C12 H7 . . 118.9 ?
C8 C12 H7 . . 118.9 ?
C12 C13 C14 . . 121.6(2) ?
C12 C13 H30 . . 119.2 ?
C14 C13 H30 . . 119.2 ?
C22 C30 H31 . . 120.0 ?
C22 C30 H32 . . 120.0 ?
H31 C30 H32 . . 120.0 ?
C13 C14 C6 . . 116.91(19) ?
C13 C14 C29 . . 120.51(19) ?
C6 C14 C29 . . 122.57(19) ?
C16 C15 C25 . . 110.83(15) ?
C16 C15 C4 . . 114.01(15) ?
C25 C15 C4 . . 110.44(15) ?
C16 C15 H25 . . 107.1 ?
C25 C15 H25 . . 107.1 ?
C4 C15 H25 . . 107.1 ?
O1 C16 C17 . . 109.81(16) ?
O1 C16 C24 . . 107.35(16) ?
C17 C16 C24 . . 105.76(16) ?
O1 C16 C15 . . 109.88(15) ?
C17 C16 C15 . . 112.01(16) ?
C24 C16 C15 . . 111.86(16) ?
O2 C17 C18 . . 123.82(18) ?
O2 C17 C16 . . 119.31(18) ?
C18 C17 C16 . . 116.46(16) ?
C3 C18 C17 . . 121.35(17) ?
C3 C18 H8 . . 119.3 ?
C17 C18 H8 . . 119.3 ?
C2 C19 C20 . . 124.82(18) ?
C2 C19 H15 . . 117.6 ?
C20 C19 H15 . . 117.6 ?
C19 C20 C21 . . 114.03(17) ?
C19 C20 H9 . . 108.7 ?
C21 C20 H9 . . 108.7 ?
C19 C20 H10 . . 108.7 ?
C21 C20 H10 . . 108.7 ?
H9 C20 H10 . . 107.6 ?
C22 C21 C20 . . 112.03(17) ?
C22 C21 C4 . . 114.50(16) ?
C20 C21 C4 . . 110.10(17) ?
C22 C21 H14 . . 106.6 ?
C20 C21 H14 . . 106.6 ?
C4 C21 H14 . . 106.6 ?
C30 C22 C23 . . 121.1(2) ?
C30 C22 C21 . . 119.31(19) ?
C23 C22 C21 . . 119.51(18) ?
C22 C23 H13 . . 109.5 ?
C22 C23 H11 . . 109.5 ?
H13 C23 H11 . . 109.5 ?
C22 C23 H12 . . 109.5 ?
H13 C23 H12 . . 109.5 ?
H11 C23 H12 . . 109.5 ?
C16 C24 H18 . . 109.5 ?
C16 C24 H19 . . 109.5 ?
H18 C24 H19 . . 109.5 ?
C16 C24 H20 . . 109.5 ?
H18 C24 H20 . . 109.5 ?
H19 C24 H20 . . 109.5 ?
C7 C25 C26 . . 108.82(16) ?
C7 C25 C15 . . 108.46(15) ?
C26 C25 C15 . . 108.96(15) ?
C7 C25 H24 . . 110.2 ?
C26 C25 H24 . . 110.2 ?
C15 C25 H24 . . 110.2 ?
O3 C26 C28 . . 111.30(16) ?
O3 C26 C27 . . 107.50(16) ?
C28 C26 C27 . . 109.27(17) ?
O3 C26 C25 . . 108.50(16) ?
C28 C26 C25 . . 112.69(16) ?
C27 C26 C25 . . 107.38(15) ?
O4 C27 C5 . . 123.84(19) ?
O4 C27 C26 . . 123.73(18) ?
C5 C27 C26 . . 112.40(16) ?
C26 C28 H22 . . 109.5 ?
C26 C28 H21 . . 109.5 ?
H22 C28 H21 . . 109.5 ?
C26 C28 H23 . . 109.5 ?
H22 C28 H23 . . 109.5 ?
H21 C28 H23 . . 109.5 ?
C14 C29 H29 . . 109.5 ?
C14 C29 H27 . . 109.5 ?
H29 C29 H27 . . 109.5 ?
C14 C29 H28 . . 109.5 ?
H29 C29 H28 . . 109.5 ?
H27 C29 H28 . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C19 C2 C3 C18 . . . . 175.23(19) ?
C1 C2 C3 C18 . . . . -3.5(3) ?
C19 C2 C3 C4 . . . . -13.3(3) ?
C1 C2 C3 C4 . . . . 168.00(18) ?
C18 C3 C4 C21 . . . . -147.56(18) ?
C2 C3 C4 C21 . . . . 41.0(2) ?
C18 C3 C4 C15 . . . . -19.6(3) ?
C2 C3 C4 C15 . . . . 168.92(16) ?
C18 C3 C4 C5 . . . . 97.0(2) ?
C2 C3 C4 C5 . . . . -74.41(19) ?
C3 C4 C5 C6 . . . . -70.00(18) ?
C21 C4 C5 C6 . . . . 172.50(15) ?
C15 C4 C5 C6 . . . . 53.15(19) ?
C3 C4 C5 C27 . . . . 174.43(15) ?
C21 C4 C5 C27 . . . . 56.92(18) ?
C15 C4 C5 C27 . . . . -62.43(18) ?
C27 C5 C6 C14 . . . . -125.6(2) ?
C4 C5 C6 C14 . . . . 118.27(19) ?
C27 C5 C6 C7 . . . . 56.7(2) ?
C4 C5 C6 C7 . . . . -59.4(2) ?
C14 C6 C7 C8 . . . . 0.0(3) ?
C5 C6 C7 C8 . . . . 177.79(17) ?
C14 C6 C7 C25 . . . . -176.29(17) ?
C5 C6 C7 C25 . . . . 1.5(2) ?
C6 C7 C8 C12 . . . . 0.6(3) ?
C25 C7 C8 C12 . . . . 176.33(19) ?
C6 C7 C8 C9 . . . . -176.48(19) ?
C25 C7 C8 C9 . . . . -0.8(3) ?
C12 C8 C9 C10 . . . . 131.6(2) ?
C7 C8 C9 C10 . . . . -51.4(3) ?
C12 C8 C9 C11 . . . . -45.9(3) ?
C7 C8 C9 C11 . . . . 131.1(3) ?
C7 C8 C12 C13 . . . . -0.3(3) ?
C9 C8 C12 C13 . . . . 176.9(2) ?
C8 C12 C13 C14 . . . . -0.6(3) ?
C12 C13 C14 C6 . . . . 1.2(3) ?
C12 C13 C14 C29 . . . . -177.8(2) ?
C7 C6 C14 C13 . . . . -0.9(3) ?
C5 C6 C14 C13 . . . . -178.48(18) ?
C7 C6 C14 C29 . . . . 178.03(19) ?
C5 C6 C14 C29 . . . . 0.5(3) ?
C3 C4 C15 C16 . . . . -7.3(2) ?
C21 C4 C15 C16 . . . . 120.73(17) ?
C5 C4 C15 C16 . . . . -121.71(17) ?
C3 C4 C15 C25 . . . . 118.27(17) ?
C21 C4 C15 C25 . . . . -113.71(17) ?
C5 C4 C15 C25 . . . . 3.85(19) ?
C25 C15 C16 O1 . . . . 35.6(2) ?
C4 C15 C16 O1 . . . . 160.93(15) ?
C25 C15 C16 C17 . . . . -86.76(19) ?
C4 C15 C16 C17 . . . . 38.6(2) ?
C25 C15 C16 C24 . . . . 154.70(16) ?
C4 C15 C16 C24 . . . . -79.9(2) ?
O1 C16 C17 O2 . . . . 16.6(3) ?
C24 C16 C17 O2 . . . . -98.9(2) ?
C15 C16 C17 O2 . . . . 139.00(18) ?
O1 C16 C17 C18 . . . . -170.42(16) ?
C24 C16 C17 C18 . . . . 74.0(2) ?
C15 C16 C17 C18 . . . . -48.0(2) ?
C2 C3 C18 C17 . . . . -176.61(18) ?
C4 C3 C18 C17 . . . . 12.3(3) ?
O2 C17 C18 C3 . . . . -164.5(2) ?
C16 C17 C18 C3 . . . . 22.9(3) ?
C3 C2 C19 C20 . . . . -1.0(3) ?
C1 C2 C19 C20 . . . . 177.69(19) ?
C2 C19 C20 C21 . . . . -14.4(3) ?
C19 C20 C21 C22 . . . . -87.5(2) ?
C19 C20 C21 C4 . . . . 41.2(2) ?
C3 C4 C21 C22 . . . . 73.2(2) ?
C15 C4 C21 C22 . . . . -57.7(2) ?
C5 C4 C21 C22 . . . . -174.61(16) ?
C3 C4 C21 C20 . . . . -54.1(2) ?
C15 C4 C21 C20 . . . . 175.01(15) ?
C5 C4 C21 C20 . . . . 58.1(2) ?
C20 C21 C22 C30 . . . . -132.3(2) ?
C4 C21 C22 C30 . . . . 101.4(2) ?
C20 C21 C22 C23 . . . . 44.8(3) ?
C4 C21 C22 C23 . . . . -81.5(2) ?
C6 C7 C25 C26 . . . . -59.9(2) ?
C8 C7 C25 C26 . . . . 124.0(2) ?
C6 C7 C25 C15 . . . . 58.5(2) ?
C8 C7 C25 C15 . . . . -117.6(2) ?
C16 C15 C25 C7 . . . . 67.7(2) ?
C4 C15 C25 C7 . . . . -59.68(19) ?
C16 C15 C25 C26 . . . . -174.03(15) ?
C4 C15 C25 C26 . . . . 58.6(2) ?
C7 C25 C26 O3 . . . . 171.70(15) ?
C15 C25 C26 O3 . . . . 53.61(19) ?
C7 C25 C26 C28 . . . . -64.6(2) ?
C15 C25 C26 C28 . . . . 177.32(16) ?
C7 C25 C26 C27 . . . . 55.8(2) ?
C15 C25 C26 C27 . . . . -62.3(2) ?
C6 C5 C27 O4 . . . . 124.5(2) ?
C4 C5 C27 O4 . . . . -118.3(2) ?
C6 C5 C27 C26 . . . . -57.0(2) ?
C4 C5 C27 C26 . . . . 60.2(2) ?
O3 C26 C27 O4 . . . . 64.2(3) ?
C28 C26 C27 O4 . . . . -56.7(3) ?
C25 C26 C27 O4 . . . . -179.3(2) ?
O3 C26 C27 C5 . . . . -114.37(17) ?
C28 C26 C27 C5 . . . . 124.72(18) ?
C25 C26 C27 C5 . . . . 2.2(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H33 O2 . 0.84 2.14 2.635(2) 117.9 ?
O3 H34 O2 1_655 0.84 1.92 2.752(2) 173.6 ?
C28 H21 O1 3_646 0.98 2.66 3.139(2) 110.7 ?

####################################################################### 
# 
# 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_shtb3c
_database_code_depnum_ccdc_archive 'CCDC 2212947'
loop_
_audit_author_name
_audit_author_address
'Xiao-Nian Li'
;Kunming Institute of Botany
China
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H22 O'
_chemical_formula_sum            'C15 H22 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         218.32
_chemical_absolute_configuration ad

_chemical_melting_point          ?

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

_cell_length_a                   8.2056(2)
_cell_length_b                   9.4771(2)
_cell_length_c                   16.4429(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1278.69(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9078
_cell_measurement_theta_min      5.3874
_cell_measurement_theta_max      72.1203
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480

_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            11438
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_theta_min         5.39
_diffrn_reflns_theta_max         72.11
_diffrn_reflns_theta_full        72.11
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             2511
_reflns_number_gt                2456
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0813
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_number_reflns         2511
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.2073P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.148
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1015 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(11)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.02172(15) 0.33758(14) 0.21382(7) 0.0263(3) Uani d . . . 1 . .
C C1 0.5397(2) 0.61712(18) 0.11286(10) 0.0223(4) Uani d . . . 1 . .
H H1 0.64536 0.640627 0.088588 0.033 Uiso calc U . R 1 . .
H H5 0.454814 0.676623 0.088765 0.033 Uiso calc U . R 1 . .
H H4 0.514615 0.517655 0.10244 0.033 Uiso calc U . R 1 . .
C C2 0.54655(19) 0.64285(16) 0.20480(9) 0.0169(3) Uani d . . . 1 . .
H H3 0.571705 0.745284 0.212265 0.02 Uiso calc U . R 1 . .
C C3 0.67871(19) 0.56220(16) 0.24915(9) 0.0146(3) Uani d . . . 1 . .
C C4 0.78990(19) 0.48318(17) 0.21016(9) 0.0166(3) Uani d . . . 1 . .
H H20 0.775754 0.467584 0.153524 0.02 Uiso calc U . R 1 . .
C C5 0.93210(19) 0.41954(17) 0.25010(9) 0.0171(3) Uani d . . . 1 . .
C C6 0.96567(18) 0.46721(17) 0.33637(9) 0.0165(3) Uani d . . . 1 . .
H H10 1.014712 0.563698 0.33368 0.02 Uiso calc U . R 1 . .
C C7 1.0860(2) 0.37161(19) 0.37997(10) 0.0222(4) Uani d . . . 1 . .
H H2 1.038019 0.277607 0.38657 0.033 Uiso calc U . R 1 . .
H H11 1.111247 0.411201 0.433563 0.033 Uiso calc U . R 1 . .
H H12 1.186283 0.364376 0.347878 0.033 Uiso calc U . R 1 . .
C C8 0.37948(19) 0.61778(18) 0.24412(10) 0.0187(3) Uani d . . . 1 . .
H H19 0.296814 0.677742 0.217124 0.022 Uiso calc U . R 1 . .
H H6 0.347298 0.517931 0.236689 0.022 Uiso calc U . R 1 . .
C C9 0.3850(2) 0.65248(18) 0.33469(10) 0.0181(3) Uani d . . . 1 . .
H H18 0.276189 0.636488 0.358979 0.022 Uiso calc U . R 1 . .
H H17 0.413351 0.753218 0.342031 0.022 Uiso calc U . R 1 . .
C C10 0.51096(18) 0.56056(16) 0.37819(9) 0.0143(3) Uani d . . . 1 . .
H H13 0.479065 0.460016 0.368853 0.017 Uiso calc U . R 1 . .
C C11 0.68328(19) 0.58058(16) 0.34089(9) 0.0142(3) Uani d . . . 1 . .
H H7 0.719726 0.679123 0.352808 0.017 Uiso calc U . R 1 . .
C C12 0.80309(18) 0.47912(17) 0.38164(9) 0.0159(3) Uani d . . . 1 . .
H H8 0.752559 0.384433 0.384952 0.019 Uiso calc U . R 1 . .
H H9 0.824145 0.511762 0.437859 0.019 Uiso calc U . R 1 . .
C C13 0.50644(18) 0.58566(18) 0.46967(9) 0.0173(3) Uani d . . . 1 . .
C C14 0.5636(2) 0.72495(18) 0.50077(10) 0.0238(4) Uani d . . . 1 . .
H H16 0.54736 0.729216 0.559769 0.036 Uiso calc U . R 1 . .
H H14 0.501257 0.80062 0.474625 0.036 Uiso calc U . R 1 . .
H H15 0.679599 0.736564 0.488358 0.036 Uiso calc U . R 1 . .
C C15 0.4455(2) 0.4880(2) 0.51926(10) 0.0231(4) Uani d . . . 1 . .
H H21 0.437567 0.506197 0.57593 0.028 Uiso calc U . R 1 . .
H H22 0.409899 0.400013 0.497969 0.028 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 . 1.225(2) ?
C1 C2 . 1.532(2) ?
C1 H1 . 0.98 ?
C1 H5 . 0.98 ?
C1 H4 . 0.98 ?
C2 C3 . 1.514(2) ?
C2 C8 . 1.534(2) ?
C2 H3 . 1.0 ?
C3 C4 . 1.343(2) ?
C3 C11 . 1.5190(19) ?
C4 C5 . 1.469(2) ?
C4 H20 . 0.95 ?
C5 C6 . 1.514(2) ?
C6 C7 . 1.520(2) ?
C6 C12 . 1.532(2) ?
C6 H10 . 1.0 ?
C7 H2 . 0.98 ?
C7 H11 . 0.98 ?
C7 H12 . 0.98 ?
C8 C9 . 1.526(2) ?
C8 H19 . 0.99 ?
C8 H6 . 0.99 ?
C9 C10 . 1.529(2) ?
C9 H18 . 0.99 ?
C9 H17 . 0.99 ?
C10 C13 . 1.523(2) ?
C10 C11 . 1.553(2) ?
C10 H13 . 1.0 ?
C11 C12 . 1.530(2) ?
C11 H7 . 1.0 ?
C12 H8 . 0.99 ?
C12 H9 . 0.99 ?
C13 C15 . 1.331(2) ?
C13 C14 . 1.491(2) ?
C14 H16 . 0.98 ?
C14 H14 . 0.98 ?
C14 H15 . 0.98 ?
C15 H21 . 0.95 ?
C15 H22 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1 . . 109.5 ?
C2 C1 H5 . . 109.5 ?
H1 C1 H5 . . 109.5 ?
C2 C1 H4 . . 109.5 ?
H1 C1 H4 . . 109.5 ?
H5 C1 H4 . . 109.5 ?
C3 C2 C1 . . 114.90(13) ?
C3 C2 C8 . . 111.03(12) ?
C1 C2 C8 . . 111.00(13) ?
C3 C2 H3 . . 106.4 ?
C1 C2 H3 . . 106.4 ?
C8 C2 H3 . . 106.4 ?
C4 C3 C2 . . 122.56(14) ?
C4 C3 C11 . . 121.41(14) ?
C2 C3 C11 . . 115.98(13) ?
C3 C4 C5 . . 123.73(14) ?
C3 C4 H20 . . 118.1 ?
C5 C4 H20 . . 118.1 ?
O1 C5 C4 . . 121.31(15) ?
O1 C5 C6 . . 122.44(15) ?
C4 C5 C6 . . 116.17(13) ?
C5 C6 C7 . . 112.47(13) ?
C5 C6 C12 . . 108.59(12) ?
C7 C6 C12 . . 112.36(13) ?
C5 C6 H10 . . 107.7 ?
C7 C6 H10 . . 107.7 ?
C12 C6 H10 . . 107.7 ?
C6 C7 H2 . . 109.5 ?
C6 C7 H11 . . 109.5 ?
H2 C7 H11 . . 109.5 ?
C6 C7 H12 . . 109.5 ?
H2 C7 H12 . . 109.5 ?
H11 C7 H12 . . 109.5 ?
C9 C8 C2 . . 110.56(13) ?
C9 C8 H19 . . 109.5 ?
C2 C8 H19 . . 109.5 ?
C9 C8 H6 . . 109.5 ?
C2 C8 H6 . . 109.5 ?
H19 C8 H6 . . 108.1 ?
C8 C9 C10 . . 110.73(13) ?
C8 C9 H18 . . 109.5 ?
C10 C9 H18 . . 109.5 ?
C8 C9 H17 . . 109.5 ?
C10 C9 H17 . . 109.5 ?
H18 C9 H17 . . 108.1 ?
C13 C10 C9 . . 110.88(12) ?
C13 C10 C11 . . 113.15(12) ?
C9 C10 C11 . . 111.16(12) ?
C13 C10 H13 . . 107.1 ?
C9 C10 H13 . . 107.1 ?
C11 C10 H13 . . 107.1 ?
C3 C11 C12 . . 112.26(13) ?
C3 C11 C10 . . 110.84(12) ?
C12 C11 C10 . . 109.60(12) ?
C3 C11 H7 . . 108.0 ?
C12 C11 H7 . . 108.0 ?
C10 C11 H7 . . 108.0 ?
C11 C12 C6 . . 113.15(12) ?
C11 C12 H8 . . 108.9 ?
C6 C12 H8 . . 108.9 ?
C11 C12 H9 . . 108.9 ?
C6 C12 H9 . . 108.9 ?
H8 C12 H9 . . 107.8 ?
C15 C13 C14 . . 121.58(15) ?
C15 C13 C10 . . 120.35(15) ?
C14 C13 C10 . . 117.98(14) ?
C13 C14 H16 . . 109.5 ?
C13 C14 H14 . . 109.5 ?
H16 C14 H14 . . 109.5 ?
C13 C14 H15 . . 109.5 ?
H16 C14 H15 . . 109.5 ?
H14 C14 H15 . . 109.5 ?
C13 C15 H21 . . 120.0 ?
C13 C15 H22 . . 120.0 ?
H21 C15 H22 . . 120.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C4 . . . . 5.2(2) ?
C8 C2 C3 C4 . . . . 132.21(16) ?
C1 C2 C3 C11 . . . . -177.30(13) ?
C8 C2 C3 C11 . . . . -50.30(18) ?
C2 C3 C4 C5 . . . . 171.40(14) ?
C11 C3 C4 C5 . . . . -5.9(2) ?
C3 C4 C5 O1 . . . . 173.06(16) ?
C3 C4 C5 C6 . . . . -10.1(2) ?
O1 C5 C6 C7 . . . . -17.6(2) ?
C4 C5 C6 C7 . . . . 165.64(13) ?
O1 C5 C6 C12 . . . . -142.58(16) ?
C4 C5 C6 C12 . . . . 40.64(18) ?
C3 C2 C8 C9 . . . . 54.40(18) ?
C1 C2 C8 C9 . . . . -176.49(13) ?
C2 C8 C9 C10 . . . . -59.62(17) ?
C8 C9 C10 C13 . . . . -175.03(13) ?
C8 C9 C10 C11 . . . . 58.19(17) ?
C4 C3 C11 C12 . . . . -11.0(2) ?
C2 C3 C11 C12 . . . . 171.47(13) ?
C4 C3 C11 C10 . . . . -133.94(15) ?
C2 C3 C11 C10 . . . . 48.55(17) ?
C13 C10 C11 C3 . . . . -176.89(13) ?
C9 C10 C11 C3 . . . . -51.35(16) ?
C13 C10 C11 C12 . . . . 58.66(17) ?
C9 C10 C11 C12 . . . . -175.80(12) ?
C3 C11 C12 C6 . . . . 43.39(18) ?
C10 C11 C12 C6 . . . . 167.01(12) ?
C5 C6 C12 C11 . . . . -57.75(17) ?
C7 C6 C12 C11 . . . . 177.19(13) ?
C9 C10 C13 C15 . . . . 107.97(17) ?
C11 C10 C13 C15 . . . . -126.35(16) ?
C9 C10 C13 C14 . . . . -68.77(18) ?
C11 C10 C13 C14 . . . . 56.91(18) ?

####################################################################### 
# 
# 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_shp3b
_database_code_depnum_ccdc_archive 'CCDC 2212950'
loop_
_audit_author_name
_audit_author_address
'Xiao-Nian Li'
;Kunming Institute of Botany
China
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H22 O'
_chemical_formula_sum            'C15 H22 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         218.32
_chemical_absolute_configuration ad

_chemical_melting_point          ?

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

_cell_length_a                   8.2085(3)
_cell_length_b                   9.4732(3)
_cell_length_c                   16.4463(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1278.88(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9807
_cell_measurement_theta_min      5.3794
_cell_measurement_theta_max      72.1976
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480

_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            31500
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_theta_min         5.38
_diffrn_reflns_theta_max         72.19
_diffrn_reflns_theta_full        72.19
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             2518
_reflns_number_gt                2488
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0791
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_number_reflns         2518
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+0.2332P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1030 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(9)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.02155(15) 0.66255(13) 0.21365(7) 0.0263(3) Uani d . . . 1 . .
C C1 0.5647(2) 0.27536(17) 0.50069(9) 0.0247(4) Uani d . . . 1 . .
H H1 0.550885 0.272207 0.55985 0.037 Uiso calc U . R 1 . .
H H10 0.680145 0.263258 0.487188 0.037 Uiso calc U . R 1 . .
H H9 0.50117 0.199334 0.475642 0.037 Uiso calc U . R 1 . .
C C2 0.50699(18) 0.41369(16) 0.46946(9) 0.0173(3) Uani d . . . 1 . .
C C3 0.51151(17) 0.43917(14) 0.37820(8) 0.0142(3) Uani d . . . 1 . .
H H8 0.479659 0.539821 0.36907 0.017 Uiso calc U . R 1 . .
C C4 0.68336(18) 0.41944(14) 0.34071(8) 0.0140(3) Uani d . . . 1 . .
H H15 0.71988 0.320847 0.352551 0.017 Uiso calc U . R 1 . .
C C15 0.4447(2) 0.51172(18) 0.51933(9) 0.0246(4) Uani d . . . 1 . .
H H21 0.436705 0.493425 0.575981 0.03 Uiso calc U . R 1 . .
H H22 0.408505 0.599499 0.498015 0.03 Uiso calc U . R 1 . .
C C5 0.67892(18) 0.43787(15) 0.24893(9) 0.0143(3) Uani d . . . 1 . .
C C6 0.54640(19) 0.35744(15) 0.20463(9) 0.0167(3) Uani d . . . 1 . .
H H4 0.571462 0.25495 0.212071 0.02 Uiso calc U . R 1 . .
C C7 0.5396(2) 0.38299(17) 0.11274(9) 0.0227(3) Uani d . . . 1 . .
H H2 0.512972 0.482183 0.102258 0.034 Uiso calc U . R 1 . .
H H5 0.455766 0.322443 0.088577 0.034 Uiso calc U . R 1 . .
H H6 0.64566 0.360704 0.088599 0.034 Uiso calc U . R 1 . .
C C8 0.93207(19) 0.58061(15) 0.24983(9) 0.0171(3) Uani d . . . 1 . .
C C9 0.96576(17) 0.53285(15) 0.33607(9) 0.0162(3) Uani d . . . 1 . .
H H3 1.015012 0.436419 0.33335 0.019 Uiso calc U . R 1 . .
C C10 0.80319(18) 0.52070(15) 0.38146(8) 0.0157(3) Uani d . . . 1 . .
H H16 0.824417 0.487803 0.437605 0.019 Uiso calc U . R 1 . .
H H17 0.752684 0.615403 0.384946 0.019 Uiso calc U . R 1 . .
C C11 0.37975(19) 0.38244(17) 0.24411(9) 0.0185(3) Uani d . . . 1 . .
H H7 0.347623 0.482367 0.236794 0.022 Uiso calc U . R 1 . .
H H13 0.296985 0.322593 0.217113 0.022 Uiso calc U . R 1 . .
C C12 0.38530(19) 0.34756(16) 0.33449(9) 0.0178(3) Uani d . . . 1 . .
H H11 0.413334 0.2467 0.341719 0.021 Uiso calc U . R 1 . .
H H12 0.276529 0.363677 0.358788 0.021 Uiso calc U . R 1 . .
C C13 0.78985(18) 0.51703(15) 0.20991(9) 0.0165(3) Uani d . . . 1 . .
H H14 0.77552 0.532788 0.153314 0.02 Uiso calc U . R 1 . .
C C14 1.08589(19) 0.62878(17) 0.37962(9) 0.0223(3) Uani d . . . 1 . .
H H18 1.186817 0.634871 0.347981 0.033 Uiso calc U . R 1 . .
H H19 1.109827 0.590122 0.433582 0.033 Uiso calc U . R 1 . .
H H20 1.038465 0.723194 0.385368 0.033 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . 1.2232(19) ?
C1 C2 . 1.485(2) ?
C1 H1 . 0.98 ?
C1 H10 . 0.98 ?
C1 H9 . 0.98 ?
C2 C15 . 1.340(2) ?
C2 C3 . 1.5207(19) ?
C3 C12 . 1.531(2) ?
C3 C4 . 1.551(2) ?
C3 H8 . 1.0 ?
C4 C5 . 1.5200(18) ?
C4 C10 . 1.529(2) ?
C4 H15 . 1.0 ?
C15 H21 . 0.95 ?
C15 H22 . 0.95 ?
C5 C13 . 1.343(2) ?
C5 C6 . 1.515(2) ?
C6 C7 . 1.5314(19) ?
C6 C11 . 1.533(2) ?
C6 H4 . 1.0 ?
C7 H2 . 0.98 ?
C7 H5 . 0.98 ?
C7 H6 . 0.98 ?
C8 C13 . 1.469(2) ?
C8 C9 . 1.5141(19) ?
C9 C14 . 1.520(2) ?
C9 C10 . 1.533(2) ?
C9 H3 . 1.0 ?
C10 H16 . 0.99 ?
C10 H17 . 0.99 ?
C11 C12 . 1.5234(19) ?
C11 H7 . 0.99 ?
C11 H13 . 0.99 ?
C12 H11 . 0.99 ?
C12 H12 . 0.99 ?
C13 H14 . 0.95 ?
C14 H18 . 0.98 ?
C14 H19 . 0.98 ?
C14 H20 . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1 . . 109.5 ?
C2 C1 H10 . . 109.5 ?
H1 C1 H10 . . 109.5 ?
C2 C1 H9 . . 109.5 ?
H1 C1 H9 . . 109.5 ?
H10 C1 H9 . . 109.5 ?
C15 C2 C1 . . 121.43(14) ?
C15 C2 C3 . . 120.21(14) ?
C1 C2 C3 . . 118.27(13) ?
C2 C3 C12 . . 110.91(12) ?
C2 C3 C4 . . 113.29(12) ?
C12 C3 C4 . . 111.14(11) ?
C2 C3 H8 . . 107.0 ?
C12 C3 H8 . . 107.0 ?
C4 C3 H8 . . 107.0 ?
C5 C4 C10 . . 112.25(12) ?
C5 C4 C3 . . 111.04(11) ?
C10 C4 C3 . . 109.60(11) ?
C5 C4 H15 . . 107.9 ?
C10 C4 H15 . . 107.9 ?
C3 C4 H15 . . 107.9 ?
C2 C15 H21 . . 120.0 ?
C2 C15 H22 . . 120.0 ?
H21 C15 H22 . . 120.0 ?
C13 C5 C6 . . 122.55(13) ?
C13 C5 C4 . . 121.49(13) ?
C6 C5 C4 . . 115.92(12) ?
C5 C6 C7 . . 114.92(13) ?
C5 C6 C11 . . 111.07(12) ?
C7 C6 C11 . . 111.16(12) ?
C5 C6 H4 . . 106.4 ?
C7 C6 H4 . . 106.4 ?
C11 C6 H4 . . 106.4 ?
C6 C7 H2 . . 109.5 ?
C6 C7 H5 . . 109.5 ?
H2 C7 H5 . . 109.5 ?
C6 C7 H6 . . 109.5 ?
H2 C7 H6 . . 109.5 ?
H5 C7 H6 . . 109.5 ?
O1 C8 C13 . . 121.34(14) ?
O1 C8 C9 . . 122.39(14) ?
C13 C8 C9 . . 116.19(12) ?
C8 C9 C14 . . 112.41(12) ?
C8 C9 C10 . . 108.63(12) ?
C14 C9 C10 . . 112.33(12) ?
C8 C9 H3 . . 107.8 ?
C14 C9 H3 . . 107.8 ?
C10 C9 H3 . . 107.8 ?
C4 C10 C9 . . 113.18(12) ?
C4 C10 H16 . . 108.9 ?
C9 C10 H16 . . 108.9 ?
C4 C10 H17 . . 108.9 ?
C9 C10 H17 . . 108.9 ?
H16 C10 H17 . . 107.8 ?
C12 C11 C6 . . 110.68(12) ?
C12 C11 H7 . . 109.5 ?
C6 C11 H7 . . 109.5 ?
C12 C11 H13 . . 109.5 ?
C6 C11 H13 . . 109.5 ?
H7 C11 H13 . . 108.1 ?
C11 C12 C3 . . 110.82(12) ?
C11 C12 H11 . . 109.5 ?
C3 C12 H11 . . 109.5 ?
C11 C12 H12 . . 109.5 ?
C3 C12 H12 . . 109.5 ?
H11 C12 H12 . . 108.1 ?
C5 C13 C8 . . 123.67(13) ?
C5 C13 H14 . . 118.2 ?
C8 C13 H14 . . 118.2 ?
C9 C14 H18 . . 109.5 ?
C9 C14 H19 . . 109.5 ?
H18 C14 H19 . . 109.5 ?
C9 C14 H20 . . 109.5 ?
H18 C14 H20 . . 109.5 ?
H19 C14 H20 . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C15 C2 C3 C12 . . . . -107.46(17) ?
C1 C2 C3 C12 . . . . 69.28(18) ?
C15 C2 C3 C4 . . . . 126.74(15) ?
C1 C2 C3 C4 . . . . -56.51(17) ?
C2 C3 C4 C5 . . . . 176.75(12) ?
C12 C3 C4 C5 . . . . 51.07(15) ?
C2 C3 C4 C10 . . . . -58.66(15) ?
C12 C3 C4 C10 . . . . 175.66(11) ?
C10 C4 C5 C13 . . . . 10.83(19) ?
C3 C4 C5 C13 . . . . 133.90(14) ?
C10 C4 C5 C6 . . . . -171.38(12) ?
C3 C4 C5 C6 . . . . -48.31(15) ?
C13 C5 C6 C7 . . . . -4.9(2) ?
C4 C5 C6 C7 . . . . 177.34(12) ?
C13 C5 C6 C11 . . . . -132.16(14) ?
C4 C5 C6 C11 . . . . 50.07(16) ?
O1 C8 C9 C14 . . . . 17.7(2) ?
C13 C8 C9 C14 . . . . -165.50(12) ?
O1 C8 C9 C10 . . . . 142.63(15) ?
C13 C8 C9 C10 . . . . -40.56(16) ?
C5 C4 C10 C9 . . . . -43.19(16) ?
C3 C4 C10 C9 . . . . -167.07(11) ?
C8 C9 C10 C4 . . . . 57.62(15) ?
C14 C9 C10 C4 . . . . -177.39(12) ?
C5 C6 C11 C12 . . . . -54.37(17) ?
C7 C6 C11 C12 . . . . 176.34(12) ?
C6 C11 C12 C3 . . . . 59.55(16) ?
C2 C3 C12 C11 . . . . 175.07(13) ?
C4 C3 C12 C11 . . . . -57.94(15) ?
C6 C5 C13 C8 . . . . -171.53(13) ?
C4 C5 C13 C8 . . . . 6.1(2) ?
O1 C8 C13 C5 . . . . -173.11(15) ?
C9 C8 C13 C5 . . . . 10.0(2) ?

