# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

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

data_20181204_29-3-2
_database_code_depnum_ccdc_archive 'CCDC 1915865'
loop_
_audit_author_name
_audit_author_address
'Xiaonian Li'
;Kunming Institute of Botany, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2020-04-16 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         'C29 H44 O4'
_chemical_formula_sum            'C29 H44 O4'
_chemical_formula_weight         456.64

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                   7.63610(10)
_cell_length_b                   16.87830(10)
_cell_length_c                   20.64040(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2660.23(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    35789
_cell_measurement_theta_min      3.3690
_cell_measurement_theta_max      73.6850

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   0.4257
_exptl_transmission_factor_max   0.6325
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.579
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.972
_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            62479
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.382
_diffrn_reflns_theta_max         73.916
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5373
_reflns_number_gt                5222
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       '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)+(0.0423P)²+0.3766P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2190 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5373
_refine_ls_number_parameters     358
_refine_ls_number_restraints     142
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0769
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.017
_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
C25 C 0.2315(7) 0.2684(3) 0.3578(2) 0.0264(9) Uani 0.543(5) 1 d . U P A 1
H25A H 0.3592 0.2616 0.3514 0.032 Uiso 0.543(5) 1 calc R U P A 1
H25B H 0.2138 0.3135 0.3876 0.032 Uiso 0.543(5) 1 calc R U P A 1
C26 C 0.1581(4) 0.19486(17) 0.38795(13) 0.0273(7) Uani 0.543(5) 1 d . U P A 1
H26B H 0.1442 0.1500 0.3606 0.033 Uiso 0.543(5) 1 calc R U P A 1
C28 C 0.1102(5) 0.1866(4) 0.44995(16) 0.0262(8) Uani 0.543(5) 1 d . U P A 1
C29 C 0.1201(6) 0.2487(3) 0.5007(3) 0.0326(10) Uani 0.543(5) 1 d . U P A 1
H29A H 0.1575 0.2988 0.4811 0.049 Uiso 0.543(5) 1 calc R U P A 1
H29B H 0.2047 0.2328 0.5340 0.049 Uiso 0.543(5) 1 calc R U P A 1
H29C H 0.0045 0.2556 0.5206 0.049 Uiso 0.543(5) 1 calc R U P A 1
C30 C 0.0395(5) 0.1078(3) 0.47434(18) 0.0337(8) Uani 0.543(5) 1 d . U P A 1
H30A H 0.0411 0.0690 0.4390 0.051 Uiso 0.543(5) 1 calc R U P A 1
H30B H -0.0809 0.1149 0.4897 0.051 Uiso 0.543(5) 1 calc R U P A 1
H30C H 0.1128 0.0887 0.5101 0.051 Uiso 0.543(5) 1 calc R U P A 1
C25A C 0.2496(8) 0.2422(3) 0.3455(3) 0.0253(11) Uani 0.457(5) 1 d . U P A 2
H25C H 0.2257 0.1847 0.3421 0.030 Uiso 0.457(5) 1 calc R U P A 2
H25D H 0.3767 0.2505 0.3389 0.030 Uiso 0.457(5) 1 calc R U P A 2
C26A C 0.1983(5) 0.2711(2) 0.41180(16) 0.0264(9) Uani 0.457(5) 1 d . U P A 2
H26A H 0.2166 0.3258 0.4201 0.032 Uiso 0.457(5) 1 calc R U P A 2
C28A C 0.1299(6) 0.2288(4) 0.4604(3) 0.0292(9) Uani 0.457(5) 1 d . U P A 2
C29A C 0.1076(8) 0.2644(4) 0.5263(3) 0.0370(12) Uani 0.457(5) 1 d . U P A 2
H29D H 0.1455 0.3198 0.5254 0.055 Uiso 0.457(5) 1 calc R U P A 2
H29E H 0.1786 0.2349 0.5576 0.055 Uiso 0.457(5) 1 calc R U P A 2
H29F H -0.0160 0.2617 0.5389 0.055 Uiso 0.457(5) 1 calc R U P A 2
C30A C 0.0773(8) 0.1442(5) 0.4551(2) 0.0432(12) Uani 0.457(5) 1 d . U P A 2
H30D H 0.0804 0.1280 0.4096 0.065 Uiso 0.457(5) 1 calc R U P A 2
H30E H -0.0416 0.1376 0.4721 0.065 Uiso 0.457(5) 1 calc R U P A 2
H30F H 0.1586 0.1114 0.4802 0.065 Uiso 0.457(5) 1 calc R U P A 2
O1 O 0.07961(16) 0.55288(7) 0.21568(6) 0.0381(3) Uani 1 1 d . . . . .
O2 O 0.28040(16) 0.41417(8) 0.31446(6) 0.0369(3) Uani 1 1 d . . . . .
O3 O 0.36669(15) 0.24491(7) 0.21757(6) 0.0329(3) Uani 1 1 d . . . . .
O4 O -0.36023(16) 0.25598(7) 0.12421(6) 0.0326(3) Uani 1 1 d . . . . .
H8 H -0.446(4) 0.2448(14) 0.1507(11) 0.049 Uiso 1 1 d . U . . .
C1 C 0.4467(3) 0.57427(12) 0.21142(15) 0.0589(6) Uani 1 1 d . . . . .
H40 H 0.5662 0.5776 0.1943 0.088 Uiso 1 1 calc R U . . .
H39 H 0.4506 0.5710 0.2588 0.088 Uiso 1 1 calc R U . . .
H1 H 0.3807 0.6215 0.1985 0.088 Uiso 1 1 calc R U . . .
C2 C 0.3574(2) 0.50082(9) 0.18451(8) 0.0299(3) Uani 1 1 d . . . . .
H38 H 0.4234 0.4531 0.1995 0.036 Uiso 1 1 calc R U . . .
C3 C 0.1697(2) 0.49443(9) 0.20841(7) 0.0272(3) Uani 1 1 d . . . . .
C4 C 0.10084(19) 0.41039(9) 0.21910(7) 0.0243(3) Uani 1 1 d . . . . .
H37 H 0.1448 0.3785 0.1817 0.029 Uiso 1 1 calc R U . . .
C5 C -0.10145(19) 0.39808(9) 0.22026(7) 0.0263(3) Uani 1 1 d . . . . .
C6 C -0.1374(2) 0.30800(9) 0.23057(7) 0.0265(3) Uani 1 1 d . . . . .
H17 H -0.2671 0.3011 0.2341 0.032 Uiso 1 1 calc R U . . .
C7 C -0.07318(19) 0.25449(9) 0.17398(7) 0.0230(3) Uani 1 1 d . . . . .
H18 H -0.0262 0.2900 0.1393 0.028 Uiso 1 1 calc R U . . .
C8 C -0.2209(2) 0.20472(10) 0.14401(7) 0.0259(3) Uani 1 1 d . . . . .
H19 H -0.2670 0.1682 0.1781 0.031 Uiso 1 1 calc R U . . .
C9 C -0.1624(2) 0.15406(9) 0.08534(7) 0.0259(3) Uani 1 1 d . . . . .
C10 C -0.0047(2) 0.10128(9) 0.10697(7) 0.0252(3) Uani 1 1 d . . . . .
H26 H -0.0500 0.0673 0.1429 0.030 Uiso 1 1 calc R U . . .
C11 C 0.0613(2) 0.04451(9) 0.05540(8) 0.0276(3) Uani 1 1 d . . . . .
C12 C 0.1973(2) 0.07167(10) 0.00882(9) 0.0330(4) Uani 1 1 d . . . . .
H4 H 0.2207 0.0296 -0.0227 0.050 Uiso 1 1 calc R U . . .
H2 H 0.3052 0.0842 0.0324 0.050 Uiso 1 1 calc R U . . .
H5 H 0.1556 0.1191 -0.0139 0.050 Uiso 1 1 calc R U . . .
C13 C 0.3509(3) 0.49993(16) 0.11076(9) 0.0580(6) Uani 1 1 d . . . . .
H41 H 0.2860 0.5463 0.0953 0.087 Uiso 1 1 calc R U . . .
H42 H 0.2921 0.4516 0.0960 0.087 Uiso 1 1 calc R U . . .
H3 H 0.4704 0.5013 0.0935 0.087 Uiso 1 1 calc R U . . .
C14 C 0.1871(2) 0.37511(10) 0.27912(7) 0.0268(3) Uani 1 1 d . . . . .
C15 C 0.1444(2) 0.28767(10) 0.29136(7) 0.0297(3) Uani 1 1 d . . . . .
C16 C 0.2116(2) 0.24223(9) 0.23175(7) 0.0263(3) Uani 1 1 d . . . . .
C17 C 0.0761(2) 0.19725(9) 0.19422(7) 0.0251(3) Uani 1 1 d . . . . .
H29 H 0.0235 0.1578 0.2247 0.030 Uiso 1 1 calc R U . . .
C18 C 0.1446(2) 0.15080(9) 0.13651(7) 0.0258(3) Uani 1 1 d . . . . .
H27 H 0.2408 0.1154 0.1505 0.031 Uiso 1 1 calc R U . . .
H28 H 0.1915 0.1878 0.1036 0.031 Uiso 1 1 calc R U . . .
C19 C 0.0013(2) -0.03053(10) 0.05325(8) 0.0337(4) Uani 1 1 d . . . . .
H6 H 0.0459 -0.0664 0.0219 0.040 Uiso 1 1 calc R U . . .
H7 H -0.0856 -0.0475 0.0831 0.040 Uiso 1 1 calc R U . . .
C20 C -0.1784(2) 0.42641(9) 0.15572(8) 0.0286(3) Uani 1 1 d . . . . .
H11 H -0.3014 0.4101 0.1528 0.043 Uiso 1 1 calc R U . . .
H10 H -0.1123 0.4030 0.1198 0.043 Uiso 1 1 calc R U . . .
H9 H -0.1709 0.4843 0.1533 0.043 Uiso 1 1 calc R U . . .
C21 C -0.1884(2) 0.44528(11) 0.27547(8) 0.0350(4) Uani 1 1 d . . . . .
H14 H -0.1882 0.5018 0.2646 0.052 Uiso 1 1 calc R U . . .
H12 H -0.1230 0.4369 0.3157 0.052 Uiso 1 1 calc R U . . .
H13 H -0.3093 0.4271 0.2812 0.052 Uiso 1 1 calc R U . . .
C22 C -0.0567(2) 0.28000(11) 0.29487(7) 0.0312(3) Uani 1 1 d . . . . .
H15 H -0.0893 0.2241 0.3030 0.037 Uiso 1 1 calc R U . . .
H16 H -0.1022 0.3126 0.3310 0.037 Uiso 1 1 calc R U . . .
C23 C -0.1184(2) 0.20771(10) 0.02761(7) 0.0295(3) Uani 1 1 d . . . . .
H22 H -0.0999 0.1751 -0.0111 0.044 Uiso 1 1 calc R U . . .
H21 H -0.0116 0.2378 0.0371 0.044 Uiso 1 1 calc R U . . .
H20 H -0.2155 0.2445 0.0200 0.044 Uiso 1 1 calc R U . . .
C24 C -0.3183(2) 0.10155(11) 0.06674(9) 0.0350(4) Uani 1 1 d . . . . .
H23 H -0.4191 0.1350 0.0560 0.053 Uiso 1 1 calc R U . . .
H25 H -0.3482 0.0669 0.1032 0.053 Uiso 1 1 calc R U . . .
H24 H -0.2872 0.0691 0.0291 0.053 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
C25 C26 1.497(6) . ?
C25 C15 1.558(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C28 1.338(5) . ?
C26 H26B 0.9500 . ?
C28 C29 1.485(7) . ?
C28 C30 1.521(6) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C25A C26A 1.505(6) . ?
C25A C15 1.576(6) . ?
C25A H25C 0.9900 . ?
C25A H25D 0.9900 . ?
C26A C28A 1.338(6) . ?
C26A H26A 0.9500 . ?
C28A C30A 1.487(8) . ?
C28A C29A 1.495(7) . ?
C29A H29D 0.9800 . ?
C29A H29E 0.9800 . ?
C29A H29F 0.9800 . ?
C30A H30D 0.9800 . ?
C30A H30E 0.9800 . ?
C30A H30F 0.9800 . ?
O1 C3 1.2119(19) . ?
O2 C14 1.2142(19) . ?
O3 C16 1.221(2) . ?
O4 C8 1.4309(19) . ?
O4 H8 0.87(3) . ?
C1 C2 1.520(3) . ?
C1 H40 0.9800 . ?
C1 H39 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.519(2) . ?
C2 C13 1.523(2) . ?
C2 H38 1.0000 . ?
C3 C4 1.529(2) . ?
C4 C14 1.524(2) . ?
C4 C5 1.559(2) . ?
C4 H37 1.0000 . ?
C5 C20 1.533(2) . ?
C5 C21 1.541(2) . ?
C5 C6 1.560(2) . ?
C6 C22 1.538(2) . ?
C6 C7 1.556(2) . ?
C6 H17 1.0000 . ?
C7 C8 1.536(2) . ?
C7 C17 1.552(2) . ?
C7 H18 1.0000 . ?
C8 C9 1.548(2) . ?
C8 H19 1.0000 . ?
C9 C24 1.533(2) . ?
C9 C23 1.534(2) . ?
C9 C10 1.563(2) . ?
C10 C11 1.518(2) . ?
C10 C18 1.540(2) . ?
C10 H26 1.0000 . ?
C11 C19 1.347(2) . ?
C11 C12 1.488(2) . ?
C12 H4 0.9800 . ?
C12 H2 0.9800 . ?
C12 H5 0.9800 . ?
C13 H41 0.9800 . ?
C13 H42 0.9800 . ?
C13 H3 0.9800 . ?
C14 C15 1.532(2) . ?
C15 C16 1.538(2) . ?
C15 C22 1.542(2) . ?
C16 C17 1.499(2) . ?
C17 C18 1.519(2) . ?
C17 H29 1.0000 . ?
C18 H27 0.9900 . ?
C18 H28 0.9900 . ?
C19 H6 0.9500 . ?
C19 H7 0.9500 . ?
C20 H11 0.9800 . ?
C20 H10 0.9800 . ?
C20 H9 0.9800 . ?
C21 H14 0.9800 . ?
C21 H12 0.9800 . ?
C21 H13 0.9800 . ?
C22 H15 0.9900 . ?
C22 H16 0.9900 . ?
C23 H22 0.9800 . ?
C23 H21 0.9800 . ?
C23 H20 0.9800 . ?
C24 H23 0.9800 . ?
C24 H25 0.9800 . ?
C24 H24 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
C26 C25 C15 112.3(3) . . ?
C26 C25 H25A 109.1 . . ?
C15 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
C15 C25 H25B 109.1 . . ?
H25A C25 H25B 107.9 . . ?
C28 C26 C25 125.9(4) . . ?
C28 C26 H26B 117.0 . . ?
C25 C26 H26B 117.0 . . ?
C26 C28 C29 126.0(5) . . ?
C26 C28 C30 120.3(4) . . ?
C29 C28 C30 113.7(3) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C26A C25A C15 110.7(4) . . ?
C26A C25A H25C 109.5 . . ?
C15 C25A H25C 109.5 . . ?
C26A C25A H25D 109.5 . . ?
C15 C25A H25D 109.5 . . ?
H25C C25A H25D 108.1 . . ?
C28A C26A C25A 127.7(4) . . ?
C28A C26A H26A 116.2 . . ?
C25A C26A H26A 116.2 . . ?
C26A C28A C30A 124.2(5) . . ?
C26A C28A C29A 120.8(6) . . ?
C30A C28A C29A 114.9(5) . . ?
C28A C29A H29D 109.5 . . ?
C28A C29A H29E 109.5 . . ?
H29D C29A H29E 109.5 . . ?
C28A C29A H29F 109.5 . . ?
H29D C29A H29F 109.5 . . ?
H29E C29A H29F 109.5 . . ?
C28A C30A H30D 109.5 . . ?
C28A C30A H30E 109.5 . . ?
H30D C30A H30E 109.5 . . ?
C28A C30A H30F 109.5 . . ?
H30D C30A H30F 109.5 . . ?
H30E C30A H30F 109.5 . . ?
C8 O4 H8 104.4(16) . . ?
C2 C1 H40 109.5 . . ?
C2 C1 H39 109.5 . . ?
H40 C1 H39 109.5 . . ?
C2 C1 H1 109.5 . . ?
H40 C1 H1 109.5 . . ?
H39 C1 H1 109.5 . . ?
C3 C2 C1 111.25(14) . . ?
C3 C2 C13 107.04(15) . . ?
C1 C2 C13 112.82(19) . . ?
C3 C2 H38 108.5 . . ?
C1 C2 H38 108.5 . . ?
C13 C2 H38 108.5 . . ?
O1 C3 C2 121.18(14) . . ?
O1 C3 C4 122.83(14) . . ?
C2 C3 C4 115.92(12) . . ?
C14 C4 C3 109.34(12) . . ?
C14 C4 C5 111.34(12) . . ?
C3 C4 C5 117.82(13) . . ?
C14 C4 H37 105.8 . . ?
C3 C4 H37 105.8 . . ?
C5 C4 H37 105.8 . . ?
C20 C5 C21 108.44(12) . . ?
C20 C5 C4 108.98(13) . . ?
C21 C5 C4 111.68(13) . . ?
C20 C5 C6 110.81(12) . . ?
C21 C5 C6 109.10(13) . . ?
C4 C5 C6 107.85(12) . . ?
C22 C6 C7 110.07(13) . . ?
C22 C6 C5 110.29(13) . . ?
C7 C6 C5 114.08(12) . . ?
C22 C6 H17 107.4 . . ?
C7 C6 H17 107.4 . . ?
C5 C6 H17 107.4 . . ?
C8 C7 C17 107.91(12) . . ?
C8 C7 C6 112.84(12) . . ?
C17 C7 C6 113.01(12) . . ?
C8 C7 H18 107.6 . . ?
C17 C7 H18 107.6 . . ?
C6 C7 H18 107.6 . . ?
O4 C8 C7 109.29(12) . . ?
O4 C8 C9 108.97(12) . . ?
C7 C8 C9 113.89(12) . . ?
O4 C8 H19 108.2 . . ?
C7 C8 H19 108.2 . . ?
C9 C8 H19 108.2 . . ?
C24 C9 C23 108.47(13) . . ?
C24 C9 C8 106.94(13) . . ?
C23 C9 C8 110.16(12) . . ?
C24 C9 C10 109.89(13) . . ?
C23 C9 C10 112.92(12) . . ?
C8 C9 C10 108.28(12) . . ?
C11 C10 C18 111.98(13) . . ?
C11 C10 C9 114.54(12) . . ?
C18 C10 C9 111.98(12) . . ?
C11 C10 H26 105.8 . . ?
C18 C10 H26 105.8 . . ?
C9 C10 H26 105.8 . . ?
C19 C11 C12 120.36(15) . . ?
C19 C11 C10 120.24(15) . . ?
C12 C11 C10 119.36(13) . . ?
C11 C12 H4 109.5 . . ?
C11 C12 H2 109.5 . . ?
H4 C12 H2 109.5 . . ?
C11 C12 H5 109.5 . . ?
H4 C12 H5 109.5 . . ?
H2 C12 H5 109.5 . . ?
C2 C13 H41 109.5 . . ?
C2 C13 H42 109.5 . . ?
H41 C13 H42 109.5 . . ?
C2 C13 H3 109.5 . . ?
H41 C13 H3 109.5 . . ?
H42 C13 H3 109.5 . . ?
O2 C14 C4 121.98(15) . . ?
O2 C14 C15 123.29(15) . . ?
C4 C14 C15 114.72(13) . . ?
C14 C15 C16 106.10(12) . . ?
C14 C15 C22 107.50(14) . . ?
C16 C15 C22 109.14(13) . . ?
C14 C15 C25 104.8(2) . . ?
C16 C15 C25 117.2(2) . . ?
C22 C15 C25 111.5(2) . . ?
C14 C15 C25A 118.5(2) . . ?
C16 C15 C25A 98.9(2) . . ?
C22 C15 C25A 115.7(3) . . ?
O3 C16 C17 124.36(15) . . ?
O3 C16 C15 119.80(14) . . ?
C17 C16 C15 115.83(13) . . ?
C16 C17 C18 115.41(13) . . ?
C16 C17 C7 109.32(12) . . ?
C18 C17 C7 111.30(12) . . ?
C16 C17 H29 106.8 . . ?
C18 C17 H29 106.8 . . ?
C7 C17 H29 106.8 . . ?
C17 C18 C10 109.62(13) . . ?
C17 C18 H27 109.7 . . ?
C10 C18 H27 109.7 . . ?
C17 C18 H28 109.7 . . ?
C10 C18 H28 109.7 . . ?
H27 C18 H28 108.2 . . ?
C11 C19 H6 120.0 . . ?
C11 C19 H7 120.0 . . ?
H6 C19 H7 120.0 . . ?
C5 C20 H11 109.5 . . ?
C5 C20 H10 109.5 . . ?
H11 C20 H10 109.5 . . ?
C5 C20 H9 109.5 . . ?
H11 C20 H9 109.5 . . ?
H10 C20 H9 109.5 . . ?
C5 C21 H14 109.5 . . ?
C5 C21 H12 109.5 . . ?
H14 C21 H12 109.5 . . ?
C5 C21 H13 109.5 . . ?
H14 C21 H13 109.5 . . ?
H12 C21 H13 109.5 . . ?
C6 C22 C15 109.43(12) . . ?
C6 C22 H15 109.8 . . ?
C15 C22 H15 109.8 . . ?
C6 C22 H16 109.8 . . ?
C15 C22 H16 109.8 . . ?
H15 C22 H16 108.2 . . ?
C9 C23 H22 109.5 . . ?
C9 C23 H21 109.5 . . ?
H22 C23 H21 109.5 . . ?
C9 C23 H20 109.5 . . ?
H22 C23 H20 109.5 . . ?
H21 C23 H20 109.5 . . ?
C9 C24 H23 109.5 . . ?
C9 C24 H25 109.5 . . ?
H23 C24 H25 109.5 . . ?
C9 C24 H24 109.5 . . ?
H23 C24 H24 109.5 . . ?
H25 C24 H24 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
C15 C25 C26 C28 -134.4(3) . . . . ?
C25 C26 C28 C29 0.3(6) . . . . ?
C25 C26 C28 C30 -179.2(3) . . . . ?
C15 C25A C26A C28A 120.6(4) . . . . ?
C25A C26A C28A C30A -5.5(7) . . . . ?
C25A C26A C28A C29A 172.0(5) . . . . ?
C1 C2 C3 O1 36.4(2) . . . . ?
C13 C2 C3 O1 -87.3(2) . . . . ?
C1 C2 C3 C4 -146.61(16) . . . . ?
C13 C2 C3 C4 89.72(18) . . . . ?
O1 C3 C4 C14 -110.93(17) . . . . ?
C2 C3 C4 C14 72.10(16) . . . . ?
O1 C3 C4 C5 17.5(2) . . . . ?
C2 C3 C4 C5 -159.49(13) . . . . ?
C14 C4 C5 C20 -173.88(12) . . . . ?
C3 C4 C5 C20 58.67(17) . . . . ?
C14 C4 C5 C21 66.35(17) . . . . ?
C3 C4 C5 C21 -61.11(18) . . . . ?
C14 C4 C5 C6 -53.52(15) . . . . ?
C3 C4 C5 C6 179.03(12) . . . . ?
C20 C5 C6 C22 178.99(12) . . . . ?
C21 C5 C6 C22 -61.69(16) . . . . ?
C4 C5 C6 C22 59.78(15) . . . . ?
C20 C5 C6 C7 54.51(17) . . . . ?
C21 C5 C6 C7 173.83(12) . . . . ?
C4 C5 C6 C7 -64.69(16) . . . . ?
C22 C6 C7 C8 113.16(14) . . . . ?
C5 C6 C7 C8 -122.24(13) . . . . ?
C22 C6 C7 C17 -9.62(17) . . . . ?
C5 C6 C7 C17 114.98(14) . . . . ?
C17 C7 C8 O4 -179.44(11) . . . . ?
C6 C7 C8 O4 54.98(15) . . . . ?
C17 C7 C8 C9 -57.32(15) . . . . ?
C6 C7 C8 C9 177.10(12) . . . . ?
O4 C8 C9 C24 -64.18(15) . . . . ?
C7 C8 C9 C24 173.52(13) . . . . ?
O4 C8 C9 C23 53.51(16) . . . . ?
C7 C8 C9 C23 -68.79(16) . . . . ?
O4 C8 C9 C10 177.45(12) . . . . ?
C7 C8 C9 C10 55.15(15) . . . . ?
C24 C9 C10 C11 60.28(16) . . . . ?
C23 C9 C10 C11 -60.98(17) . . . . ?
C8 C9 C10 C11 176.75(12) . . . . ?
C24 C9 C10 C18 -170.82(13) . . . . ?
C23 C9 C10 C18 67.93(16) . . . . ?
C8 C9 C10 C18 -54.34(15) . . . . ?
C18 C10 C11 C19 137.05(15) . . . . ?
C9 C10 C11 C19 -94.05(17) . . . . ?
C18 C10 C11 C12 -40.78(19) . . . . ?
C9 C10 C11 C12 88.13(17) . . . . ?
C3 C4 C14 O2 7.03(19) . . . . ?
C5 C4 C14 O2 -124.89(15) . . . . ?
C3 C4 C14 C15 -173.82(12) . . . . ?
C5 C4 C14 C15 54.26(16) . . . . ?
O2 C14 C15 C16 -120.15(16) . . . . ?
C4 C14 C15 C16 60.71(16) . . . . ?
O2 C14 C15 C22 123.18(16) . . . . ?
C4 C14 C15 C22 -55.96(16) . . . . ?
O2 C14 C15 C25 4.5(3) . . . . ?
C4 C14 C15 C25 -174.7(2) . . . . ?
O2 C14 C15 C25A -10.3(3) . . . . ?
C4 C14 C15 C25A 170.5(3) . . . . ?
C26 C25 C15 C14 161.7(3) . . . . ?
C26 C25 C15 C16 -81.0(4) . . . . ?
C26 C25 C15 C22 45.7(4) . . . . ?
C26A C25A C15 C14 70.4(5) . . . . ?
C26A C25A C15 C16 -175.8(4) . . . . ?
C26A C25A C15 C22 -59.5(4) . . . . ?
C14 C15 C16 O3 59.77(18) . . . . ?
C22 C15 C16 O3 175.32(14) . . . . ?
C25 C15 C16 O3 -56.8(3) . . . . ?
C25A C15 C16 O3 -63.5(3) . . . . ?
C14 C15 C16 C17 -119.73(14) . . . . ?
C22 C15 C16 C17 -4.17(18) . . . . ?
C25 C15 C16 C17 123.7(2) . . . . ?
C25A C15 C16 C17 117.1(3) . . . . ?
O3 C16 C17 C18 2.1(2) . . . . ?
C15 C16 C17 C18 -178.43(12) . . . . ?
O3 C16 C17 C7 -124.25(16) . . . . ?
C15 C16 C17 C7 55.22(16) . . . . ?
C8 C7 C17 C16 -172.35(12) . . . . ?
C6 C7 C17 C16 -46.86(16) . . . . ?
C8 C7 C17 C18 58.99(15) . . . . ?
C6 C7 C17 C18 -175.53(12) . . . . ?
C16 C17 C18 C10 174.36(12) . . . . ?
C7 C17 C18 C10 -60.30(15) . . . . ?
C11 C10 C18 C17 -171.63(12) . . . . ?
C9 C10 C18 C17 58.13(15) . . . . ?
C7 C6 C22 C15 62.11(17) . . . . ?
C5 C6 C22 C15 -64.64(17) . . . . ?
C14 C15 C22 C6 59.77(17) . . . . ?
C16 C15 C22 C6 -54.89(18) . . . . ?
C25 C15 C22 C6 174.1(2) . . . . ?
C25A C15 C22 C6 -165.2(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
C17 H29 O1 1.00 2.30 3.2879(18) 171.2 3_545
O4 H8 O3 0.87(3) 1.99(3) 2.8454(17) 167(2) 1_455
C17 H29 O1 1.00 2.30 3.2879(18) 171.2 3_545
O4 H8 O3 0.87(3) 1.99(3) 2.8454(17) 167(2) 1_455
C17 H29 O1 1.00 2.30 3.2879(18) 171.2 3_545
O4 H8 O3 0.87(3) 1.99(3) 2.8454(17) 167(2) 1_455
C17 H29 O1 1.00 2.30 3.2879(18) 171.2 3_545
O4 H8 O3 0.87(3) 1.99(3) 2.8454(17) 167(2) 1_455
O4 H8 O3 0.87(3) 1.99(3) 2.8454(17) 167(2) 1_455
C17 H29 O1 1.00 2.30 3.2879(18) 171.2 3_545
O4 H8 O3 0.87(3) 1.99(3) 2.8454(17) 167(2) 1_455
C17 H29 O1 1.00 2.30 3.2879(18) 171.2 3_545

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032



####################################################################### 
# 
# 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_20190623_XSS27-18
_database_code_depnum_ccdc_archive 'CCDC 1963372'
loop_
_audit_author_name
_audit_author_address
'Xianggao Meng'
;Central China Normal University
China
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H42 O4'
_chemical_formula_weight         490.65

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                   11.64760(10)
_cell_length_b                   12.38710(10)
_cell_length_c                   18.71260(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2699.85(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    22702
_cell_measurement_theta_min      4.2870
_cell_measurement_theta_max      73.5880

_exptl_crystal_description       bulk
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.610
_shelx_estimated_absorpt_T_min   0.888
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31151
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.280
_diffrn_reflns_theta_max         74.019
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5430
_reflns_number_gt                5306
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2274 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5430
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.913
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.62196(10) 0.39825(8) 0.47463(6) 0.0210(2) Uani 1 1 d . . . . .
O2 O 0.55685(11) 1.00242(9) 0.69116(7) 0.0297(3) Uani 1 1 d . . . . .
O3 O 0.39080(10) 0.81805(10) 0.76577(5) 0.0240(2) Uani 1 1 d . . . . .
O4 O 0.66217(9) 0.74670(8) 0.61197(6) 0.0204(2) Uani 1 1 d . . . . .
C1 C -0.10317(14) 0.59698(16) 0.69025(10) 0.0313(4) Uani 1 1 d . . . . .
H1A H -0.114514 0.630846 0.644644 0.047 Uiso 1 1 calc R U . . .
H1B H -0.168719 0.610183 0.720096 0.047 Uiso 1 1 calc R U . . .
H1C H -0.093687 0.520629 0.683724 0.047 Uiso 1 1 calc R U . . .
C2 C 0.00241(13) 0.64286(13) 0.72514(9) 0.0229(3) Uani 1 1 d . . . . .
C3 C 0.06571(13) 0.71744(14) 0.69124(8) 0.0231(3) Uani 1 1 d . . . . .
H3 H 0.039978 0.738283 0.646265 0.028 Uiso 1 1 calc R U . . .
C4 C 0.17344(13) 0.77126(14) 0.71753(9) 0.0230(3) Uani 1 1 d . . . . .
H4A H 0.188516 0.748068 0.766144 0.028 Uiso 1 1 calc R U . . .
H4B H 0.161783 0.848791 0.718226 0.028 Uiso 1 1 calc R U . . .
C5 C 0.27861(12) 0.74522(11) 0.67081(8) 0.0174(3) Uani 1 1 d . . . . .
H5 H 0.290332 0.667025 0.674000 0.021 Uiso 1 1 calc R U . . .
C6 C 0.38612(13) 0.79777(11) 0.70215(7) 0.0168(3) Uani 1 1 d . . . . .
C7 C 0.49010(12) 0.82644(11) 0.65434(8) 0.0167(3) Uani 1 1 d . . . . .
C8 C 0.56528(12) 0.72874(11) 0.63276(7) 0.0158(3) Uani 1 1 d . . . . .
C9 C 0.51506(12) 0.61579(11) 0.63481(7) 0.0151(3) Uani 1 1 d . . . . .
H9 H 0.470650 0.607484 0.678949 0.018 Uiso 1 1 calc R U . . .
C10 C 0.60549(12) 0.52651(11) 0.63153(8) 0.0176(3) Uani 1 1 d . . . . .
H10A H 0.627647 0.504173 0.679259 0.021 Uiso 1 1 calc R U . . .
H10B H 0.673318 0.551197 0.606276 0.021 Uiso 1 1 calc R U . . .
C11 C 0.54800(12) 0.43271(11) 0.59111(7) 0.0162(3) Uani 1 1 d . . . . .
H11 H 0.499132 0.390440 0.623269 0.019 Uiso 1 1 calc R U . . .
C12 C 0.62923(13) 0.35799(11) 0.54819(7) 0.0189(3) Uani 1 1 d . . . . .
C13 C 0.75473(13) 0.36138(13) 0.57087(9) 0.0248(3) Uani 1 1 d . . . . .
H13A H 0.798968 0.314876 0.540433 0.037 Uiso 1 1 calc R U . . .
H13B H 0.761412 0.337445 0.619482 0.037 Uiso 1 1 calc R U . . .
H13C H 0.782945 0.433963 0.566978 0.037 Uiso 1 1 calc R U . . .
C14 C 0.02719(16) 0.59880(15) 0.79819(9) 0.0292(4) Uani 1 1 d . . . . .
H14A H 0.040218 0.522425 0.795053 0.044 Uiso 1 1 calc R U . . .
H14B H -0.037085 0.612441 0.829003 0.044 Uiso 1 1 calc R U . . .
H14C H 0.094309 0.633351 0.817257 0.044 Uiso 1 1 calc R U . . .
C15 C 0.25618(12) 0.77055(12) 0.59135(8) 0.0186(3) Uani 1 1 d . . . . .
H15A H 0.216332 0.709545 0.570345 0.022 Uiso 1 1 calc R U . . .
H15B H 0.204999 0.832198 0.588718 0.022 Uiso 1 1 calc R U . . .
C16 C 0.36269(13) 0.79489(11) 0.54560(7) 0.0182(3) Uani 1 1 d . . . . .
H16 H 0.333146 0.832005 0.503162 0.022 Uiso 1 1 calc R U . . .
C17 C 0.41983(13) 0.69077(12) 0.51681(7) 0.0184(3) Uani 1 1 d . . . . .
H17A H 0.375274 0.665641 0.476302 0.022 Uiso 1 1 calc R U . . .
H17B H 0.495510 0.709580 0.499125 0.022 Uiso 1 1 calc R U . . .
C18 C 0.43316(12) 0.59642(11) 0.56920(7) 0.0159(3) Uani 1 1 d . . . . .
H18 H 0.356686 0.581721 0.588742 0.019 Uiso 1 1 calc R U . . .
C19 C 0.58702(15) 0.24123(12) 0.54877(8) 0.0259(3) Uani 1 1 d . . . . .
H19A H 0.506911 0.239418 0.536756 0.039 Uiso 1 1 calc R U . . .
H19B H 0.597976 0.210968 0.595500 0.039 Uiso 1 1 calc R U . . .
H19C H 0.629639 0.199931 0.514403 0.039 Uiso 1 1 calc R U . . .
C20 C 0.56672(13) 0.50144(11) 0.47602(8) 0.0185(3) Uani 1 1 d . . . . .
H20A H 0.532204 0.517762 0.430104 0.022 Uiso 1 1 calc R U . . .
H20B H 0.621012 0.558008 0.487986 0.022 Uiso 1 1 calc R U . . .
C21 C 0.47498(12) 0.49059(11) 0.53387(7) 0.0161(3) Uani 1 1 d . . . . .
C22 C 0.37273(13) 0.42673(13) 0.50444(8) 0.0215(3) Uani 1 1 d . . . . .
H22A H 0.327126 0.472752 0.474483 0.032 Uiso 1 1 calc R U . . .
H22B H 0.326744 0.400822 0.543412 0.032 Uiso 1 1 calc R U . . .
H22C H 0.400267 0.366582 0.477001 0.032 Uiso 1 1 calc R U . . .
C23 C 0.56696(13) 0.90569(12) 0.69884(8) 0.0190(3) Uani 1 1 d . . . . .
C24 C 0.65346(13) 0.86432(12) 0.75153(8) 0.0176(3) Uani 1 1 d . . . . .
C25 C 0.64923(13) 0.76321(12) 0.78476(8) 0.0196(3) Uani 1 1 d . . . . .
H25 H 0.590822 0.714935 0.773484 0.023 Uiso 1 1 calc R U . . .
C26 C 0.73231(14) 0.73499(12) 0.83458(8) 0.0216(3) Uani 1 1 d . . . . .
H26 H 0.728897 0.667999 0.856916 0.026 Uiso 1 1 calc R U . . .
C27 C 0.82081(14) 0.80638(13) 0.85136(8) 0.0230(3) Uani 1 1 d . . . . .
H27 H 0.876927 0.786581 0.884196 0.028 Uiso 1 1 calc R U . . .
C28 C 0.82497(14) 0.90702(13) 0.81897(9) 0.0254(3) Uani 1 1 d . . . . .
H28 H 0.883470 0.955129 0.830366 0.030 Uiso 1 1 calc R U . . .
C29 C 0.74175(13) 0.93570(12) 0.76960(8) 0.0219(3) Uani 1 1 d . . . . .
H29 H 0.744668 1.003399 0.748187 0.026 Uiso 1 1 calc R U . . .
C30 C 0.44086(12) 0.87919(11) 0.58349(8) 0.0177(3) Uani 1 1 d . . . . .
C31 C 0.36562(14) 0.97858(12) 0.60147(8) 0.0224(3) Uani 1 1 d . . . . .
H31A H 0.315058 0.993452 0.562174 0.034 Uiso 1 1 calc R U . . .
H31B H 0.414038 1.040014 0.609847 0.034 Uiso 1 1 calc R U . . .
H31C H 0.321123 0.963913 0.643549 0.034 Uiso 1 1 calc R U . . .
C32 C 0.53589(14) 0.91855(13) 0.53280(8) 0.0235(3) Uani 1 1 d . . . . .
H32A H 0.582910 0.858513 0.518810 0.035 Uiso 1 1 calc R U . . .
H32B H 0.582351 0.971316 0.556791 0.035 Uiso 1 1 calc R U . . .
H32C H 0.501752 0.950413 0.491139 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 C20 1.4313(17) . ?
O1 C12 1.4666(17) . ?
O2 C23 1.2125(19) . ?
O3 C6 1.2178(18) . ?
O4 C8 1.2143(19) . ?
C1 C2 1.504(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.341(2) . ?
C2 C14 1.500(2) . ?
C3 C4 1.504(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.539(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.5283(19) . ?
C5 C15 1.5420(19) . ?
C5 H5 0.9800 . ?
C6 C7 1.5471(19) . ?
C7 C8 1.5474(18) . ?
C7 C23 1.568(2) . ?
C7 C30 1.5853(19) . ?
C8 C9 1.5169(19) . ?
C9 C10 1.5284(19) . ?
C9 C18 1.5733(19) . ?
C9 H9 0.9800 . ?
C10 C11 1.5397(19) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C21 1.5443(19) . ?
C11 C12 1.5482(19) . ?
C11 H11 0.9800 . ?
C12 C13 1.523(2) . ?
C12 C19 1.528(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.537(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.5481(19) . ?
C16 C30 1.556(2) . ?
C16 H16 0.9800 . ?
C17 C18 1.5332(19) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C21 1.5468(18) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.5270(19) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.5321(19) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.500(2) . ?
C24 C29 1.398(2) . ?
C24 C25 1.399(2) . ?
C25 C26 1.388(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.394(2) . ?
C26 H26 0.9300 . ?
C27 C28 1.387(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.385(2) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C32 1.537(2) . ?
C30 C31 1.5483(19) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 C12 108.21(10) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C14 125.15(15) . . ?
C3 C2 C1 120.29(15) . . ?
C14 C2 C1 114.56(15) . . ?
C2 C3 C4 127.54(14) . . ?
C2 C3 H3 116.2 . . ?
C4 C3 H3 116.2 . . ?
C3 C4 C5 112.67(12) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 110.17(11) . . ?
C6 C5 C15 114.98(12) . . ?
C4 C5 C15 111.73(12) . . ?
C6 C5 H5 106.5 . . ?
C4 C5 H5 106.5 . . ?
C15 C5 H5 106.5 . . ?
O3 C6 C5 119.98(13) . . ?
O3 C6 C7 118.88(13) . . ?
C5 C6 C7 121.15(11) . . ?
C6 C7 C8 114.48(11) . . ?
C6 C7 C23 106.47(11) . . ?
C8 C7 C23 107.76(11) . . ?
C6 C7 C30 107.16(11) . . ?
C8 C7 C30 107.99(11) . . ?
C23 C7 C30 113.12(12) . . ?
O4 C8 C9 122.37(13) . . ?
O4 C8 C7 117.79(12) . . ?
C9 C8 C7 119.77(12) . . ?
C8 C9 C10 113.62(11) . . ?
C8 C9 C18 110.78(11) . . ?
C10 C9 C18 106.03(11) . . ?
C8 C9 H9 108.8 . . ?
C10 C9 H9 108.8 . . ?
C18 C9 H9 108.8 . . ?
C9 C10 C11 105.43(11) . . ?
C9 C10 H10A 110.7 . . ?
C11 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C10 C11 C21 103.29(11) . . ?
C10 C11 C12 116.12(12) . . ?
C21 C11 C12 104.74(11) . . ?
C10 C11 H11 110.7 . . ?
C21 C11 H11 110.7 . . ?
C12 C11 H11 110.7 . . ?
O1 C12 C13 107.91(12) . . ?
O1 C12 C19 108.06(12) . . ?
C13 C12 C19 109.46(13) . . ?
O1 C12 C11 104.37(11) . . ?
C13 C12 C11 115.19(12) . . ?
C19 C12 C11 111.45(12) . . ?
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 . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C5 116.12(12) . . ?
C16 C15 H15A 108.3 . . ?
C5 C15 H15A 108.3 . . ?
C16 C15 H15B 108.3 . . ?
C5 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
C15 C16 C17 112.17(12) . . ?
C15 C16 C30 110.49(11) . . ?
C17 C16 C30 117.78(12) . . ?
C15 C16 H16 105.1 . . ?
C17 C16 H16 105.1 . . ?
C30 C16 H16 105.1 . . ?
C18 C17 C16 117.14(12) . . ?
C18 C17 H17A 108.0 . . ?
C16 C17 H17A 108.0 . . ?
C18 C17 H17B 108.0 . . ?
C16 C17 H17B 108.0 . . ?
H17A C17 H17B 107.3 . . ?
C17 C18 C21 113.87(12) . . ?
C17 C18 C9 116.37(11) . . ?
C21 C18 C9 105.77(11) . . ?
C17 C18 H18 106.8 . . ?
C21 C18 H18 106.8 . . ?
C9 C18 H18 106.8 . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 C21 104.42(11) . . ?
O1 C20 H20A 110.9 . . ?
C21 C20 H20A 110.9 . . ?
O1 C20 H20B 110.9 . . ?
C21 C20 H20B 110.9 . . ?
H20A C20 H20B 108.9 . . ?
C20 C21 C22 109.55(11) . . ?
C20 C21 C11 98.46(11) . . ?
C22 C21 C11 115.95(12) . . ?
C20 C21 C18 116.66(11) . . ?
C22 C21 C18 110.27(12) . . ?
C11 C21 C18 105.70(11) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 C24 118.73(14) . . ?
O2 C23 C7 120.02(14) . . ?
C24 C23 C7 121.25(13) . . ?
C29 C24 C25 118.98(14) . . ?
C29 C24 C23 115.92(14) . . ?
C25 C24 C23 125.06(14) . . ?
C26 C25 C24 119.95(14) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.46(14) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 119.84(14) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C29 C28 C27 119.83(14) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C24 120.92(14) . . ?
C28 C29 H29 119.5 . . ?
C24 C29 H29 119.5 . . ?
C32 C30 C31 106.82(12) . . ?
C32 C30 C16 110.67(12) . . ?
C31 C30 C16 107.54(11) . . ?
C32 C30 C7 112.73(12) . . ?
C31 C30 C7 110.53(12) . . ?
C16 C30 C7 108.43(11) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C4 -179.57(15) . . . . ?
C2 C3 C4 C5 116.53(18) . . . . ?
C3 C4 C5 C6 -177.36(13) . . . . ?
C3 C4 C5 C15 53.54(17) . . . . ?
C4 C5 C6 O3 25.30(19) . . . . ?
C15 C5 C6 O3 152.61(13) . . . . ?
C4 C5 C6 C7 -154.50(12) . . . . ?
C15 C5 C6 C7 -27.18(18) . . . . ?
O3 C6 C7 C8 103.86(15) . . . . ?
C5 C6 C7 C8 -76.35(16) . . . . ?
O3 C6 C7 C23 -15.10(17) . . . . ?
C5 C6 C7 C23 164.70(12) . . . . ?
O3 C6 C7 C30 -136.42(13) . . . . ?
C5 C6 C7 C30 43.38(16) . . . . ?
C6 C7 C8 O4 -161.10(13) . . . . ?
C23 C7 C8 O4 -42.88(17) . . . . ?
C30 C7 C8 O4 79.64(15) . . . . ?
C6 C7 C8 C9 21.72(18) . . . . ?
C23 C7 C8 C9 139.94(12) . . . . ?
C30 C7 C8 C9 -97.54(14) . . . . ?
O4 C8 C9 C10 18.2(2) . . . . ?
C7 C8 C9 C10 -164.78(12) . . . . ?
O4 C8 C9 C18 -101.06(15) . . . . ?
C7 C8 C9 C18 75.99(15) . . . . ?
C8 C9 C10 C11 -147.48(12) . . . . ?
C18 C9 C10 C11 -25.58(14) . . . . ?
C9 C10 C11 C21 37.04(14) . . . . ?
C9 C10 C11 C12 151.06(12) . . . . ?
C20 O1 C12 C13 -109.77(13) . . . . ?
C20 O1 C12 C19 131.96(13) . . . . ?
C20 O1 C12 C11 13.23(14) . . . . ?
C10 C11 C12 O1 -97.95(14) . . . . ?
C21 C11 C12 O1 15.24(13) . . . . ?
C10 C11 C12 C13 20.18(17) . . . . ?
C21 C11 C12 C13 133.37(13) . . . . ?
C10 C11 C12 C19 145.66(13) . . . . ?
C21 C11 C12 C19 -101.16(13) . . . . ?
C6 C5 C15 C16 28.26(17) . . . . ?
C4 C5 C15 C16 154.78(12) . . . . ?
C5 C15 C16 C17 84.97(15) . . . . ?
C5 C15 C16 C30 -48.62(16) . . . . ?
C15 C16 C17 C18 -43.69(17) . . . . ?
C30 C16 C17 C18 86.24(16) . . . . ?
C16 C17 C18 C21 171.84(12) . . . . ?
C16 C17 C18 C9 -64.72(16) . . . . ?
C8 C9 C18 C17 0.38(16) . . . . ?
C10 C9 C18 C17 -123.32(13) . . . . ?
C8 C9 C18 C21 127.93(12) . . . . ?
C10 C9 C18 C21 4.23(14) . . . . ?
C12 O1 C20 C21 -37.21(14) . . . . ?
O1 C20 C21 C22 -77.24(14) . . . . ?
O1 C20 C21 C11 44.25(13) . . . . ?
O1 C20 C21 C18 156.63(12) . . . . ?
C10 C11 C21 C20 86.64(12) . . . . ?
C12 C11 C21 C20 -35.35(12) . . . . ?
C10 C11 C21 C22 -156.70(12) . . . . ?
C12 C11 C21 C22 81.30(14) . . . . ?
C10 C11 C21 C18 -34.22(13) . . . . ?
C12 C11 C21 C18 -156.21(11) . . . . ?
C17 C18 C21 C20 39.46(17) . . . . ?
C9 C18 C21 C20 -89.57(14) . . . . ?
C17 C18 C21 C22 -86.32(14) . . . . ?
C9 C18 C21 C22 144.66(12) . . . . ?
C17 C18 C21 C11 147.64(12) . . . . ?
C9 C18 C21 C11 18.61(13) . . . . ?
C6 C7 C23 O2 -95.35(17) . . . . ?
C8 C7 C23 O2 141.39(15) . . . . ?
C30 C7 C23 O2 22.1(2) . . . . ?
C6 C7 C23 C24 84.41(15) . . . . ?
C8 C7 C23 C24 -38.85(17) . . . . ?
C30 C7 C23 C24 -158.15(12) . . . . ?
O2 C23 C24 C29 -21.2(2) . . . . ?
C7 C23 C24 C29 159.00(13) . . . . ?
O2 C23 C24 C25 156.38(15) . . . . ?
C7 C23 C24 C25 -23.4(2) . . . . ?
C29 C24 C25 C26 -0.3(2) . . . . ?
C23 C24 C25 C26 -177.85(14) . . . . ?
C24 C25 C26 C27 -0.6(2) . . . . ?
C25 C26 C27 C28 1.1(2) . . . . ?
C26 C27 C28 C29 -0.6(2) . . . . ?
C27 C28 C29 C24 -0.3(2) . . . . ?
C25 C24 C29 C28 0.8(2) . . . . ?
C23 C24 C29 C28 178.52(14) . . . . ?
C15 C16 C30 C32 -170.15(11) . . . . ?
C17 C16 C30 C32 59.15(16) . . . . ?
C15 C16 C30 C31 -53.81(15) . . . . ?
C17 C16 C30 C31 175.49(11) . . . . ?
C15 C16 C30 C7 65.73(14) . . . . ?
C17 C16 C30 C7 -64.97(15) . . . . ?
C6 C7 C30 C32 176.28(11) . . . . ?
C8 C7 C30 C32 -59.92(15) . . . . ?
C23 C7 C30 C32 59.25(15) . . . . ?
C6 C7 C30 C31 56.82(14) . . . . ?
C8 C7 C30 C31 -179.39(11) . . . . ?
C23 C7 C30 C31 -60.22(15) . . . . ?
C6 C7 C30 C16 -60.83(14) . . . . ?
C8 C7 C30 C16 62.97(14) . . . . ?
C23 C7 C30 C16 -177.87(11) . . . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037



