# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 
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data_cu_zyh_lyy3212_0m
_database_code_depnum_ccdc_archive 'CCDC 1860578'
_audit_update_record             
;
2018-08-07 deposited with the CCDC.
2018-10-18 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         'C21 H32 O5'
_chemical_formula_sum            'C21 H32 O5'
_chemical_formula_weight         364.46

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                   8.8265(2)
_cell_length_b                   21.6150(4)
_cell_length_c                   30.7813(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5872.6(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9830
_cell_measurement_theta_min      5.60
_cell_measurement_theta_max      70.22

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             2376
_exptl_transmission_factor_min   0.5586
_exptl_transmission_factor_max   0.7533
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.701
_shelx_estimated_absorpt_T_min   0.787
_shelx_estimated_absorpt_T_max   0.914
_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            36203
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         5.000
_diffrn_reflns_theta_max         70.357
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             10479
_reflns_number_gt                10427
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_max     0.876
_reflns_Friedel_fraction_full    0.916

_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)+(0.0510P)²+1.2619P] 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 4270 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         10479
_refine_ls_number_parameters     727
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0821
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_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
O16 O -0.00417(18) 0.21734(6) 0.91638(4) 0.0255(3) Uani 1 1 d . . . . .
O3 O -0.01152(14) 0.10945(6) 0.86664(4) 0.0138(3) Uani 1 1 d . . . . .
H3 H -0.0015 0.0889 0.8437 0.021 Uiso 1 1 calc R U . . .
O8 O 0.76191(14) 0.07032(6) 0.92589(4) 0.0169(3) Uani 1 1 d . . . . .
H8 H 0.8219 0.0869 0.9082 0.025 Uiso 1 1 calc R U . . .
O10 O 0.40556(14) -0.07504(6) 0.95429(4) 0.0128(2) Uani 1 1 d . . . . .
H10 H 0.3286 -0.0585 0.9654 0.019 Uiso 1 1 calc R U . . .
O12 O 0.37252(14) -0.00830(6) 0.80682(4) 0.0151(3) Uani 1 1 d . . . . .
O6 O -0.00535(16) 0.23144(6) 0.23600(4) 0.0194(3) Uani 1 1 d . . . . .
O7 O 0.00410(14) 0.12124(6) 0.19112(4) 0.0132(3) Uani 1 1 d . . . . .
H7 H 0.0173 0.0982 0.1695 0.020 Uiso 1 1 calc R U . . .
O1 O 0.40938(15) 0.00143(6) 0.13988(4) 0.0153(3) Uani 1 1 d . . . . .
O9 O 0.42266(14) -0.04364(6) 0.29131(4) 0.0127(2) Uani 1 1 d . . . . .
H9 H 0.3440 -0.0261 0.3005 0.019 Uiso 1 1 calc R U . . .
O2 O 0.77737(14) 0.09947(6) 0.25438(4) 0.0160(3) Uani 1 1 d . . . . .
H2 H 0.8386 0.1106 0.2350 0.024 Uiso 1 1 calc R U . . .
O11 O 1.05703(16) 0.72199(6) 0.90718(4) 0.0193(3) Uani 1 1 d . . . . .
O4 O 1.03145(14) 0.62747(6) 0.96751(4) 0.0138(3) Uani 1 1 d . . . . .
H4 H 1.0122 0.6110 0.9916 0.021 Uiso 1 1 calc R U . . .
O13 O 0.61541(14) 0.44640(6) 0.88024(4) 0.0136(3) Uani 1 1 d . . . . .
H13 H 0.6944 0.4622 0.8699 0.020 Uiso 1 1 calc R U . . .
O14 O 0.61873(14) 0.52116(6) 1.02588(4) 0.0151(3) Uani 1 1 d . . . . .
O15 O 0.25984(14) 0.59329(6) 0.90596(4) 0.0174(3) Uani 1 1 d . . . . .
H15 H 0.2006 0.6078 0.9247 0.026 Uiso 1 1 calc R U . . .
C19 C 0.7862(2) -0.08766(9) 0.94686(6) 0.0208(4) Uani 1 1 d . . . . .
H19A H 0.8404 -0.0532 0.9332 0.031 Uiso 1 1 calc R U . . .
H19B H 0.8595 -0.1179 0.9579 0.031 Uiso 1 1 calc R U . . .
H19C H 0.7247 -0.0720 0.9710 0.031 Uiso 1 1 calc R U . . .
C15 C 0.6830(2) -0.11886(8) 0.91326(6) 0.0143(4) Uani 1 1 d . . . . .
H15A H 0.6229 -0.1509 0.9292 0.017 Uiso 1 1 calc R U . . .
C14 C 0.5707(2) -0.07585(8) 0.89222(5) 0.0118(3) Uani 1 1 d . . . . .
C10 C 0.4563(2) -0.03870(8) 0.91851(5) 0.0116(3) Uani 1 1 d . . . . .
C11 C 0.3276(2) -0.02577(8) 0.88415(5) 0.0115(3) Uani 1 1 d . . . . .
C1 C 0.2312(2) 0.03172(8) 0.88876(5) 0.0109(3) Uani 1 1 d . . . . .
H1 H 0.1314 0.0242 0.8991 0.013 Uiso 1 1 calc R U . . .
C2 C 0.2619(2) 0.09116(8) 0.88090(5) 0.0118(3) Uani 1 1 d . . . . .
C3 C 0.1298(2) 0.13764(8) 0.87761(6) 0.0133(3) Uani 1 1 d . . . . .
C16 C 0.1035(2) 0.16920(8) 0.92119(6) 0.0160(4) Uani 1 1 d . . . . .
H16A H 0.0661 0.1386 0.9426 0.019 Uiso 1 1 calc R U . . .
H16B H 0.2001 0.1864 0.9321 0.019 Uiso 1 1 calc R U . . .
C21 C -0.0400(3) 0.24539(12) 0.95627(8) 0.0392(6) Uani 1 1 d . . . . .
H21A H -0.0877 0.2149 0.9755 0.059 Uiso 1 1 calc R U . . .
H21B H -0.1101 0.2798 0.9513 0.059 Uiso 1 1 calc R U . . .
H21C H 0.0529 0.2610 0.9699 0.059 Uiso 1 1 calc R U . . .
C6 C 0.4078(2) 0.12278(8) 0.86603(5) 0.0122(3) Uani 1 1 d . . . . .
H6 H 0.4439 0.0999 0.8397 0.015 Uiso 1 1 calc R U . . .
C7 C 0.5444(2) 0.12722(8) 0.89762(5) 0.0135(4) Uani 1 1 d . . . . .
H7A H 0.6233 0.1517 0.8818 0.016 Uiso 1 1 calc R U . . .
C8 C 0.6159(2) 0.06361(8) 0.90604(5) 0.0123(3) Uani 1 1 d . . . . .
H8A H 0.6284 0.0418 0.8776 0.015 Uiso 1 1 calc R U . . .
C9 C 0.5236(2) 0.02209(8) 0.93675(5) 0.0114(3) Uani 1 1 d . . . . .
H9A H 0.4387 0.0471 0.9484 0.014 Uiso 1 1 calc R U . . .
H9B H 0.5893 0.0112 0.9617 0.014 Uiso 1 1 calc R U . . .
C12 C 0.4163(2) -0.02911(8) 0.84153(5) 0.0117(3) Uani 1 1 d . . . . .
C13 C 0.5531(2) -0.06582(8) 0.84937(6) 0.0132(3) Uani 1 1 d . . . . .
H13A H 0.6197 -0.0804 0.8274 0.016 Uiso 1 1 calc R U . . .
C20 C 0.7796(2) -0.15331(9) 0.87984(6) 0.0208(4) Uani 1 1 d . . . . .
H20A H 0.7133 -0.1757 0.8597 0.031 Uiso 1 1 calc R U . . .
H20B H 0.8461 -0.1827 0.8948 0.031 Uiso 1 1 calc R U . . .
H20C H 0.8412 -0.1236 0.8636 0.031 Uiso 1 1 calc R U . . .
C18 C 0.2197(2) -0.08233(8) 0.88178(6) 0.0139(3) Uani 1 1 d . . . . .
H18A H 0.1578 -0.0840 0.9082 0.021 Uiso 1 1 calc R U . . .
H18B H 0.2796 -0.1204 0.8793 0.021 Uiso 1 1 calc R U . . .
H18C H 0.1536 -0.0783 0.8563 0.021 Uiso 1 1 calc R U . . .
C17 C 0.5153(2) 0.16226(8) 0.93996(6) 0.0187(4) Uani 1 1 d . . . . .
H17A H 0.4295 0.1435 0.9552 0.028 Uiso 1 1 calc R U . . .
H17B H 0.4921 0.2056 0.9334 0.028 Uiso 1 1 calc R U . . .
H17C H 0.6058 0.1602 0.9584 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3559(2) 0.18772(8) 0.85043(6) 0.0162(4) Uani 1 1 d . . . . .
H5A H 0.3764 0.2193 0.8730 0.019 Uiso 1 1 calc R U . . .
H5B H 0.4096 0.1996 0.8234 0.019 Uiso 1 1 calc R U . . .
C4 C 0.1861(2) 0.18198(8) 0.84222(6) 0.0149(4) Uani 1 1 d . . . . .
H4A H 0.1662 0.1649 0.8129 0.018 Uiso 1 1 calc R U . . .
H4B H 0.1358 0.2228 0.8447 0.018 Uiso 1 1 calc R U . . .
C22 C 0.6816(2) -0.15036(9) 0.26322(7) 0.0211(4) Uani 1 1 d . . . . .
H22A H 0.5801 -0.1550 0.2757 0.032 Uiso 1 1 calc R U . . .
H22B H 0.7561 -0.1700 0.2824 0.032 Uiso 1 1 calc R U . . .
H22C H 0.6846 -0.1702 0.2346 0.032 Uiso 1 1 calc R U . . .
C23 C 0.7191(2) -0.08136(8) 0.25851(6) 0.0144(4) Uani 1 1 d . . . . .
H23 H 0.7187 -0.0625 0.2882 0.017 Uiso 1 1 calc R U . . .
C24 C 0.5998(2) -0.04978(8) 0.23191(6) 0.0115(3) Uani 1 1 d . . . . .
C25 C 0.47687(19) -0.01192(8) 0.25376(5) 0.0113(3) Uani 1 1 d . . . . .
C26 C 0.35405(19) -0.00613(8) 0.21739(5) 0.0110(3) Uani 1 1 d . . . . .
C27 C 0.2521(2) 0.04980(8) 0.21782(5) 0.0112(3) Uani 1 1 d . . . . .
H27 H 0.1518 0.0418 0.2276 0.013 Uiso 1 1 calc R U . . .
C28 C 0.2780(2) 0.10862(8) 0.20688(5) 0.0108(3) Uani 1 1 d . . . . .
C29 C 0.14233(19) 0.15257(8) 0.20113(5) 0.0116(3) Uani 1 1 d . . . . .
C30 C 0.1108(2) 0.18742(8) 0.24312(6) 0.0145(4) Uani 1 1 d . . . . .
H30A H 0.0793 0.1580 0.2660 0.017 Uiso 1 1 calc R U . . .
H30B H 0.2041 0.2086 0.2530 0.017 Uiso 1 1 calc R U . . .
C31 C -0.0532(3) 0.25946(10) 0.27512(7) 0.0252(4) Uani 1 1 d . . . . .
H31A H -0.0943 0.2278 0.2946 0.038 Uiso 1 1 calc R U . . .
H31B H -0.1317 0.2902 0.2688 0.038 Uiso 1 1 calc R U . . .
H31C H 0.0333 0.2798 0.2891 0.038 Uiso 1 1 calc R U . . .
C32 C 0.1958(2) 0.19454(8) 0.16395(6) 0.0138(4) Uani 1 1 d . . . . .
H32A H 0.1765 0.1749 0.1354 0.017 Uiso 1 1 calc R U . . .
H32B H 0.1430 0.2349 0.1649 0.017 Uiso 1 1 calc R U . . .
C33 C 0.3654(2) 0.20269(8) 0.17160(6) 0.0148(4) Uani 1 1 d . . . . .
H33A H 0.3843 0.2370 0.1922 0.018 Uiso 1 1 calc R U . . .
H33B H 0.4180 0.2119 0.1440 0.018 Uiso 1 1 calc R U . . .
C34 C 0.4216(2) 0.14054(8) 0.19075(5) 0.0123(3) Uani 1 1 d . . . . .
H34 H 0.4608 0.1154 0.1659 0.015 Uiso 1 1 calc R U . . .
C35 C 0.4490(2) -0.01432(8) 0.17623(5) 0.0122(3) Uani 1 1 d . . . . .
C36 C 0.5872(2) -0.04761(8) 0.18833(6) 0.0136(3) Uani 1 1 d . . . . .
H36 H 0.6575 -0.0651 0.1684 0.016 Uiso 1 1 calc R U . . .
C37 C 0.5422(2) 0.05058(8) 0.26871(5) 0.0116(3) Uani 1 1 d . . . . .
H37A H 0.4570 0.0763 0.2793 0.014 Uiso 1 1 calc R U . . .
H37B H 0.6094 0.0427 0.2938 0.014 Uiso 1 1 calc R U . . .
C38 C 0.63157(19) 0.08897(8) 0.23539(5) 0.0116(3) Uani 1 1 d . . . . .
H38 H 0.6453 0.0635 0.2086 0.014 Uiso 1 1 calc R U . . .
C39 C 0.5566(2) 0.15032(8) 0.22252(5) 0.0128(3) Uani 1 1 d . . . . .
H39 H 0.6348 0.1737 0.2057 0.015 Uiso 1 1 calc R U . . .
C40 C 0.5222(2) 0.18994(8) 0.26251(6) 0.0172(4) Uani 1 1 d . . . . .
H40A H 0.4329 0.1734 0.2775 0.026 Uiso 1 1 calc R U . . .
H40B H 0.5023 0.2326 0.2534 0.026 Uiso 1 1 calc R U . . .
H40C H 0.6093 0.1892 0.2822 0.026 Uiso 1 1 calc R U . . .
C41 C 0.8772(2) -0.07294(10) 0.23916(7) 0.0221(4) Uani 1 1 d . . . . .
H41A H 0.8801 -0.0912 0.2100 0.033 Uiso 1 1 calc R U . . .
H41B H 0.9519 -0.0935 0.2577 0.033 Uiso 1 1 calc R U . . .
H41C H 0.9008 -0.0287 0.2373 0.033 Uiso 1 1 calc R U . . .
C42 C 0.2532(2) -0.06494(8) 0.21783(6) 0.0137(3) Uani 1 1 d . . . . .
H42A H 0.1958 -0.0665 0.2450 0.020 Uiso 1 1 calc R U . . .
H42B H 0.3174 -0.1018 0.2155 0.020 Uiso 1 1 calc R U . . .
H42C H 0.1828 -0.0636 0.1932 0.020 Uiso 1 1 calc R U . . .
C43 C 0.1593(2) 0.42555(10) 0.93261(7) 0.0243(4) Uani 1 1 d . . . . .
H43A H 0.1534 0.4138 0.9633 0.037 Uiso 1 1 calc R U . . .
H43B H 0.0861 0.4012 0.9159 0.037 Uiso 1 1 calc R U . . .
H43C H 0.1360 0.4697 0.9295 0.037 Uiso 1 1 calc R U . . .
C44 C 0.3187(2) 0.41305(9) 0.91565(6) 0.0163(4) Uani 1 1 d . . . . .
H44 H 0.3216 0.4250 0.8843 0.020 Uiso 1 1 calc R U . . .
C45 C 0.4361(2) 0.45041(8) 0.93907(6) 0.0128(3) Uani 1 1 d . . . . .
C46 C 0.5594(2) 0.48450(8) 0.91452(5) 0.0118(3) Uani 1 1 d . . . . .
C47 C 0.6803(2) 0.49764(8) 0.95037(5) 0.0119(3) Uani 1 1 d . . . . .
C48 C 0.7828(2) 0.55316(8) 0.94516(5) 0.0114(3) Uani 1 1 d . . . . .
H48 H 0.8834 0.5429 0.9369 0.014 Uiso 1 1 calc R U . . .
C49 C 0.7592(2) 0.61392(8) 0.94988(5) 0.0118(3) Uani 1 1 d . . . . .
C50 C 0.8985(2) 0.65702(8) 0.95122(6) 0.0131(4) Uani 1 1 d . . . . .
C51 C 0.9385(2) 0.67776(8) 0.90544(6) 0.0146(4) Uani 1 1 d . . . . .
H51A H 0.9710 0.6417 0.8880 0.017 Uiso 1 1 calc R U . . .
H51B H 0.8484 0.6962 0.8914 0.017 Uiso 1 1 calc R U . . .
C52 C 1.1110(3) 0.73602(10) 0.86513(7) 0.0257(4) Uani 1 1 d . . . . .
H52A H 1.1496 0.6983 0.8514 0.039 Uiso 1 1 calc R U . . .
H52B H 1.1928 0.7666 0.8672 0.039 Uiso 1 1 calc R U . . .
H52C H 1.0282 0.7530 0.8476 0.039 Uiso 1 1 calc R U . . .
C53 C 0.3562(2) 0.34396(9) 0.91888(8) 0.0271(5) Uani 1 1 d . . . . .
H53A H 0.4587 0.3367 0.9078 0.041 Uiso 1 1 calc R U . . .
H53B H 0.2832 0.3202 0.9016 0.041 Uiso 1 1 calc R U . . .
H53C H 0.3506 0.3308 0.9493 0.041 Uiso 1 1 calc R U . . .
C54 C 0.4462(2) 0.46133(8) 0.98212(6) 0.0140(3) Uani 1 1 d . . . . .
H54 H 0.3753 0.4476 1.0033 0.017 Uiso 1 1 calc R U . . .
C55 C 0.5824(2) 0.49740(8) 0.99138(5) 0.0119(3) Uani 1 1 d . . . . .
C56 C 0.4957(2) 0.54396(8) 0.89392(5) 0.0125(3) Uani 1 1 d . . . . .
H56A H 0.5811 0.5670 0.8808 0.015 Uiso 1 1 calc R U . . .
H56B H 0.4270 0.5318 0.8700 0.015 Uiso 1 1 calc R U . . .
C57 C 0.4090(2) 0.58840(8) 0.92398(5) 0.0126(3) Uani 1 1 d . . . . .
H57 H 0.4012 0.5690 0.9534 0.015 Uiso 1 1 calc R U . . .
C58 C 0.4822(2) 0.65233(8) 0.92886(6) 0.0148(4) Uani 1 1 d . . . . .
H58 H 0.4033 0.6792 0.9426 0.018 Uiso 1 1 calc R U . . .
C59 C 0.6173(2) 0.65143(8) 0.96117(6) 0.0140(4) Uani 1 1 d . . . . .
H59 H 0.5779 0.6350 0.9894 0.017 Uiso 1 1 calc R U . . .
C60 C 0.6774(2) 0.71750(9) 0.97006(7) 0.0209(4) Uani 1 1 d . . . . .
H60A H 0.6634 0.7441 0.9442 0.025 Uiso 1 1 calc R U . . .
H60B H 0.6233 0.7364 0.9949 0.025 Uiso 1 1 calc R U . . .
C61 C 0.8455(2) 0.70999(9) 0.98042(6) 0.0168(4) Uani 1 1 d . . . . .
H61A H 0.8604 0.6995 1.0114 0.020 Uiso 1 1 calc R U . . .
H61B H 0.9017 0.7485 0.9738 0.020 Uiso 1 1 calc R U . . .
C62 C 0.5156(2) 0.68160(9) 0.88444(6) 0.0203(4) Uani 1 1 d . . . . .
H62A H 0.6084 0.6636 0.8724 0.030 Uiso 1 1 calc R U . . .
H62B H 0.5290 0.7263 0.8879 0.030 Uiso 1 1 calc R U . . .
H62C H 0.4308 0.6736 0.8647 0.030 Uiso 1 1 calc R U . . .
C63 C 0.7816(2) 0.43953(8) 0.95556(6) 0.0141(4) Uani 1 1 d . . . . .
H63A H 0.8420 0.4337 0.9292 0.021 Uiso 1 1 calc R U . . .
H63B H 0.7175 0.4031 0.9603 0.021 Uiso 1 1 calc R U . . .
H63C H 0.8492 0.4451 0.9805 0.021 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
O16 C21 1.405(3) . ?
O16 C16 1.417(2) . ?
O3 C3 1.428(2) . ?
O3 H3 0.8400 . ?
O8 C8 1.434(2) . ?
O8 H8 0.8400 . ?
O10 C10 1.425(2) . ?
O10 H10 0.8400 . ?
O12 C12 1.222(2) . ?
O6 C31 1.413(2) . ?
O6 C30 1.416(2) . ?
O7 C29 1.429(2) . ?
O7 H7 0.8400 . ?
O1 C35 1.221(2) . ?
O9 C25 1.427(2) . ?
O9 H9 0.8400 . ?
O2 C38 1.431(2) . ?
O2 H2 0.8400 . ?
O11 C52 1.412(2) . ?
O11 C51 1.418(2) . ?
O4 C50 1.427(2) . ?
O4 H4 0.8400 . ?
O13 C46 1.427(2) . ?
O13 H13 0.8400 . ?
O14 C55 1.222(2) . ?
O15 C57 1.433(2) . ?
O15 H15 0.8400 . ?
C19 C15 1.534(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C15 C14 1.505(2) . ?
C15 C20 1.529(3) . ?
C15 H15A 1.0000 . ?
C14 C13 1.346(2) . ?
C14 C10 1.523(2) . ?
C10 C9 1.547(2) . ?
C10 C11 1.577(2) . ?
C11 C1 1.513(2) . ?
C11 C12 1.529(2) . ?
C11 C18 1.552(2) . ?
C1 C2 1.335(3) . ?
C1 H1 0.9500 . ?
C2 C6 1.528(2) . ?
C2 C3 1.543(2) . ?
C3 C16 1.523(2) . ?
C3 C4 1.534(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C6 C7 1.552(2) . ?
C6 C5 1.553(2) . ?
C6 H6 1.0000 . ?
C7 C17 1.529(2) . ?
C7 C8 1.535(2) . ?
C7 H7A 1.0000 . ?
C8 C9 1.537(2) . ?
C8 H8A 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C12 C13 1.465(2) . ?
C13 H13A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C5 C4 1.525(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C22 C23 1.535(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.499(2) . ?
C23 C41 1.528(2) . ?
C23 H23 1.0000 . ?
C24 C36 1.347(2) . ?
C24 C25 1.516(2) . ?
C25 C37 1.539(2) . ?
C25 C26 1.563(2) . ?
C26 C27 1.507(2) . ?
C26 C35 1.530(2) . ?
C26 C42 1.552(2) . ?
C27 C28 1.335(3) . ?
C27 H27 0.9500 . ?
C28 C34 1.526(2) . ?
C28 C29 1.539(2) . ?
C29 C30 1.521(2) . ?
C29 C32 1.535(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.526(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.549(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C39 1.556(2) . ?
C34 H34 1.0000 . ?
C35 C36 1.464(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.537(2) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.534(2) . ?
C38 H38 1.0000 . ?
C39 C40 1.530(2) . ?
C39 H39 1.0000 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.524(3) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 C45 1.498(3) . ?
C44 C53 1.533(3) . ?
C44 H44 1.0000 . ?
C45 C54 1.349(2) . ?
C45 C46 1.516(2) . ?
C46 C56 1.540(2) . ?
C46 C47 1.562(2) . ?
C47 C48 1.511(2) . ?
C47 C55 1.530(2) . ?
C47 C63 1.550(2) . ?
C48 C49 1.338(3) . ?
C48 H48 0.9500 . ?
C49 C59 1.532(2) . ?
C49 C50 1.543(2) . ?
C50 C51 1.520(2) . ?
C50 C61 1.529(2) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 C55 1.461(3) . ?
C54 H54 0.9500 . ?
C56 C57 1.537(2) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
C57 C58 1.533(2) . ?
C57 H57 1.0000 . ?
C58 C62 1.535(3) . ?
C58 C59 1.553(2) . ?
C58 H58 1.0000 . ?
C59 C60 1.548(3) . ?
C59 H59 1.0000 . ?
C60 C61 1.526(3) . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 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 O16 C16 112.12(15) . . ?
C3 O3 H3 109.5 . . ?
C8 O8 H8 109.5 . . ?
C10 O10 H10 109.5 . . ?
C31 O6 C30 111.87(14) . . ?
C29 O7 H7 109.5 . . ?
C25 O9 H9 109.5 . . ?
C38 O2 H2 109.5 . . ?
C52 O11 C51 111.06(15) . . ?
C50 O4 H4 109.5 . . ?
C46 O13 H13 109.5 . . ?
C57 O15 H15 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C15 C20 112.22(15) . . ?
C14 C15 C19 114.17(15) . . ?
C20 C15 C19 109.68(16) . . ?
C14 C15 H15A 106.8 . . ?
C20 C15 H15A 106.8 . . ?
C19 C15 H15A 106.8 . . ?
C13 C14 C15 126.68(16) . . ?
C13 C14 C10 111.04(15) . . ?
C15 C14 C10 122.26(15) . . ?
O10 C10 C14 109.18(13) . . ?
O10 C10 C9 107.95(13) . . ?
C14 C10 C9 112.72(14) . . ?
O10 C10 C11 112.93(14) . . ?
C14 C10 C11 102.40(13) . . ?
C9 C10 C11 111.66(13) . . ?
C1 C11 C12 114.03(14) . . ?
C1 C11 C18 107.83(14) . . ?
C12 C11 C18 103.68(14) . . ?
C1 C11 C10 119.19(14) . . ?
C12 C11 C10 101.45(13) . . ?
C18 C11 C10 109.51(13) . . ?
C2 C1 C11 131.26(16) . . ?
C2 C1 H1 114.4 . . ?
C11 C1 H1 114.4 . . ?
C1 C2 C6 130.94(16) . . ?
C1 C2 C3 119.05(16) . . ?
C6 C2 C3 109.04(14) . . ?
O3 C3 C16 105.45(14) . . ?
O3 C3 C4 112.44(14) . . ?
C16 C3 C4 113.28(14) . . ?
O3 C3 C2 113.43(13) . . ?
C16 C3 C2 110.44(14) . . ?
C4 C3 C2 102.03(14) . . ?
O16 C16 C3 109.84(14) . . ?
O16 C16 H16A 109.7 . . ?
C3 C16 H16A 109.7 . . ?
O16 C16 H16B 109.7 . . ?
C3 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
O16 C21 H21A 109.5 . . ?
O16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 C6 C7 119.66(14) . . ?
C2 C6 C5 104.36(14) . . ?
C7 C6 C5 111.55(14) . . ?
C2 C6 H6 106.9 . . ?
C7 C6 H6 106.9 . . ?
C5 C6 H6 106.9 . . ?
C17 C7 C8 111.65(14) . . ?
C17 C7 C6 115.73(15) . . ?
C8 C7 C6 111.69(14) . . ?
C17 C7 H7A 105.6 . . ?
C8 C7 H7A 105.6 . . ?
C6 C7 H7A 105.6 . . ?
O8 C8 C7 110.53(14) . . ?
O8 C8 C9 105.87(13) . . ?
C7 C8 C9 114.16(15) . . ?
O8 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C8 C9 C10 118.42(14) . . ?
C8 C9 H9A 107.7 . . ?
C10 C9 H9A 107.7 . . ?
C8 C9 H9B 107.7 . . ?
C10 C9 H9B 107.7 . . ?
H9A C9 H9B 107.1 . . ?
O12 C12 C13 127.15(16) . . ?
O12 C12 C11 124.83(16) . . ?
C13 C12 C11 107.82(14) . . ?
C14 C13 C12 110.14(15) . . ?
C14 C13 H13A 124.9 . . ?
C12 C13 H13A 124.9 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C5 C6 105.53(14) . . ?
C4 C5 H5A 110.6 . . ?
C6 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
C6 C5 H5B 110.6 . . ?
H5A C5 H5B 108.8 . . ?
C5 C4 C3 104.59(14) . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C41 112.00(15) . . ?
C24 C23 C22 110.03(15) . . ?
C41 C23 C22 110.48(15) . . ?
C24 C23 H23 108.1 . . ?
C41 C23 H23 108.1 . . ?
C22 C23 H23 108.1 . . ?
C36 C24 C23 128.15(16) . . ?
C36 C24 C25 111.35(15) . . ?
C23 C24 C25 120.43(15) . . ?
O9 C25 C24 109.87(13) . . ?
O9 C25 C37 107.76(13) . . ?
C24 C25 C37 109.78(14) . . ?
O9 C25 C26 112.71(14) . . ?
C24 C25 C26 102.82(13) . . ?
C37 C25 C26 113.80(14) . . ?
C27 C26 C35 115.30(14) . . ?
C27 C26 C42 108.32(14) . . ?
C35 C26 C42 103.10(13) . . ?
C27 C26 C25 118.18(14) . . ?
C35 C26 C25 101.76(13) . . ?
C42 C26 C25 109.02(14) . . ?
C28 C27 C26 131.23(16) . . ?
C28 C27 H27 114.4 . . ?
C26 C27 H27 114.4 . . ?
C27 C28 C34 130.93(16) . . ?
C27 C28 C29 118.90(15) . . ?
C34 C28 C29 109.27(14) . . ?
O7 C29 C30 105.18(14) . . ?
O7 C29 C32 112.44(14) . . ?
C30 C29 C32 113.39(14) . . ?
O7 C29 C28 113.37(14) . . ?
C30 C29 C28 110.50(14) . . ?
C32 C29 C28 102.20(14) . . ?
O6 C30 C29 109.48(14) . . ?
O6 C30 H30A 109.8 . . ?
C29 C30 H30A 109.8 . . ?
O6 C30 H30B 109.8 . . ?
C29 C30 H30B 109.8 . . ?
H30A C30 H30B 108.2 . . ?
O6 C31 H31A 109.5 . . ?
O6 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O6 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C29 104.76(14) . . ?
C33 C32 H32A 110.8 . . ?
C29 C32 H32A 110.8 . . ?
C33 C32 H32B 110.8 . . ?
C29 C32 H32B 110.8 . . ?
H32A C32 H32B 108.9 . . ?
C32 C33 C34 105.86(14) . . ?
C32 C33 H33A 110.6 . . ?
C34 C33 H33A 110.6 . . ?
C32 C33 H33B 110.6 . . ?
C34 C33 H33B 110.6 . . ?
H33A C33 H33B 108.7 . . ?
C28 C34 C33 104.45(14) . . ?
C28 C34 C39 119.54(14) . . ?
C33 C34 C39 111.53(14) . . ?
C28 C34 H34 106.9 . . ?
C33 C34 H34 106.9 . . ?
C39 C34 H34 106.9 . . ?
O1 C35 C36 127.53(16) . . ?
O1 C35 C26 124.73(16) . . ?
C36 C35 C26 107.61(14) . . ?
C24 C36 C35 109.82(16) . . ?
C24 C36 H36 125.1 . . ?
C35 C36 H36 125.1 . . ?
C38 C37 C25 117.80(14) . . ?
C38 C37 H37A 107.9 . . ?
C25 C37 H37A 107.9 . . ?
C38 C37 H37B 107.9 . . ?
C25 C37 H37B 107.9 . . ?
H37A C37 H37B 107.2 . . ?
O2 C38 C39 110.87(14) . . ?
O2 C38 C37 105.94(13) . . ?
C39 C38 C37 114.66(14) . . ?
O2 C38 H38 108.4 . . ?
C39 C38 H38 108.4 . . ?
C37 C38 H38 108.4 . . ?
C40 C39 C38 111.21(14) . . ?
C40 C39 C34 115.46(15) . . ?
C38 C39 C34 112.04(14) . . ?
C40 C39 H39 105.8 . . ?
C38 C39 H39 105.8 . . ?
C34 C39 H39 105.8 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C23 C41 H41A 109.5 . . ?
C23 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C23 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C26 C42 H42A 109.5 . . ?
C26 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C26 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 H43A 109.5 . . ?
C44 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C44 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C45 C44 C43 112.19(15) . . ?
C45 C44 C53 110.17(16) . . ?
C43 C44 C53 110.46(17) . . ?
C45 C44 H44 108.0 . . ?
C43 C44 H44 108.0 . . ?
C53 C44 H44 108.0 . . ?
C54 C45 C44 127.79(17) . . ?
C54 C45 C46 110.93(16) . . ?
C44 C45 C46 121.22(15) . . ?
O13 C46 C45 109.69(14) . . ?
O13 C46 C56 107.69(13) . . ?
C45 C46 C56 110.41(14) . . ?
O13 C46 C47 113.00(14) . . ?
C45 C46 C47 103.11(13) . . ?
C56 C46 C47 112.89(14) . . ?
C48 C47 C55 115.36(14) . . ?
C48 C47 C63 108.04(14) . . ?
C55 C47 C63 103.76(14) . . ?
C48 C47 C46 118.59(14) . . ?
C55 C47 C46 101.32(14) . . ?
C63 C47 C46 108.64(14) . . ?
C49 C48 C47 132.46(17) . . ?
C49 C48 H48 113.8 . . ?
C47 C48 H48 113.8 . . ?
C48 C49 C59 132.19(17) . . ?
C48 C49 C50 118.14(16) . . ?
C59 C49 C50 109.01(14) . . ?
O4 C50 C51 105.45(14) . . ?
O4 C50 C61 112.35(14) . . ?
C51 C50 C61 113.28(15) . . ?
O4 C50 C49 113.22(14) . . ?
C51 C50 C49 109.79(14) . . ?
C61 C50 C49 102.94(14) . . ?
O11 C51 C50 109.60(14) . . ?
O11 C51 H51A 109.8 . . ?
C50 C51 H51A 109.8 . . ?
O11 C51 H51B 109.8 . . ?
C50 C51 H51B 109.8 . . ?
H51A C51 H51B 108.2 . . ?
O11 C52 H52A 109.5 . . ?
O11 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
O11 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C44 C53 H53A 109.5 . . ?
C44 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C44 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C45 C54 C55 109.83(16) . . ?
C45 C54 H54 125.1 . . ?
C55 C54 H54 125.1 . . ?
O14 C55 C54 127.54(16) . . ?
O14 C55 C47 124.56(16) . . ?
C54 C55 C47 107.82(14) . . ?
C57 C56 C46 117.10(14) . . ?
C57 C56 H56A 108.0 . . ?
C46 C56 H56A 108.0 . . ?
C57 C56 H56B 108.0 . . ?
C46 C56 H56B 108.0 . . ?
H56A C56 H56B 107.3 . . ?
O15 C57 C58 111.01(14) . . ?
O15 C57 C56 105.68(13) . . ?
C58 C57 C56 114.38(15) . . ?
O15 C57 H57 108.5 . . ?
C58 C57 H57 108.5 . . ?
C56 C57 H57 108.5 . . ?
C57 C58 C62 111.42(15) . . ?
C57 C58 C59 112.02(14) . . ?
C62 C58 C59 115.36(16) . . ?
C57 C58 H58 105.7 . . ?
C62 C58 H58 105.7 . . ?
C59 C58 H58 105.7 . . ?
C49 C59 C60 104.35(14) . . ?
C49 C59 C58 119.28(14) . . ?
C60 C59 C58 111.41(15) . . ?
C49 C59 H59 107.1 . . ?
C60 C59 H59 107.1 . . ?
C58 C59 H59 107.1 . . ?
C61 C60 C59 105.80(15) . . ?
C61 C60 H60A 110.6 . . ?
C59 C60 H60A 110.6 . . ?
C61 C60 H60B 110.6 . . ?
C59 C60 H60B 110.6 . . ?
H60A C60 H60B 108.7 . . ?
C60 C61 C50 104.74(15) . . ?
C60 C61 H61A 110.8 . . ?
C50 C61 H61A 110.8 . . ?
C60 C61 H61B 110.8 . . ?
C50 C61 H61B 110.8 . . ?
H61A C61 H61B 108.9 . . ?
C58 C62 H62A 109.5 . . ?
C58 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C58 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C47 C63 H63A 109.5 . . ?
C47 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C47 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 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
C20 C15 C14 C13 -1.1(3) . . . . ?
C19 C15 C14 C13 124.5(2) . . . . ?
C20 C15 C14 C10 176.92(16) . . . . ?
C19 C15 C14 C10 -57.5(2) . . . . ?
C13 C14 C10 O10 141.72(15) . . . . ?
C15 C14 C10 O10 -36.6(2) . . . . ?
C13 C14 C10 C9 -98.32(17) . . . . ?
C15 C14 C10 C9 83.35(19) . . . . ?
C13 C14 C10 C11 21.79(19) . . . . ?
C15 C14 C10 C11 -156.54(15) . . . . ?
O10 C10 C11 C1 90.93(18) . . . . ?
C14 C10 C11 C1 -151.79(15) . . . . ?
C9 C10 C11 C1 -30.9(2) . . . . ?
O10 C10 C11 C12 -142.96(14) . . . . ?
C14 C10 C11 C12 -25.69(16) . . . . ?
C9 C10 C11 C12 95.16(15) . . . . ?
O10 C10 C11 C18 -33.83(19) . . . . ?
C14 C10 C11 C18 83.45(16) . . . . ?
C9 C10 C11 C18 -155.70(14) . . . . ?
C12 C11 C1 C2 -45.4(3) . . . . ?
C18 C11 C1 C2 -159.93(18) . . . . ?
C10 C11 C1 C2 74.5(2) . . . . ?
C11 C1 C2 C6 -2.7(3) . . . . ?
C11 C1 C2 C3 164.70(16) . . . . ?
C1 C2 C3 O3 -23.1(2) . . . . ?
C6 C2 C3 O3 146.83(14) . . . . ?
C1 C2 C3 C16 94.98(19) . . . . ?
C6 C2 C3 C16 -95.05(16) . . . . ?
C1 C2 C3 C4 -144.31(16) . . . . ?
C6 C2 C3 C4 25.66(17) . . . . ?
C21 O16 C16 C3 176.12(19) . . . . ?
O3 C3 C16 O16 -64.72(18) . . . . ?
C4 C3 C16 O16 58.6(2) . . . . ?
C2 C3 C16 O16 172.38(15) . . . . ?
C1 C2 C6 C7 -70.3(2) . . . . ?
C3 C2 C6 C7 121.30(16) . . . . ?
C1 C2 C6 C5 164.07(18) . . . . ?
C3 C2 C6 C5 -4.30(18) . . . . ?
C2 C6 C7 C17 -60.1(2) . . . . ?
C5 C6 C7 C17 62.0(2) . . . . ?
C2 C6 C7 C8 69.1(2) . . . . ?
C5 C6 C7 C8 -168.76(14) . . . . ?
C17 C7 C8 O8 -63.26(18) . . . . ?
C6 C7 C8 O8 165.40(13) . . . . ?
C17 C7 C8 C9 56.0(2) . . . . ?
C6 C7 C8 C9 -75.39(18) . . . . ?
O8 C8 C9 C10 -122.56(15) . . . . ?
C7 C8 C9 C10 115.63(17) . . . . ?
O10 C10 C9 C8 167.58(14) . . . . ?
C14 C10 C9 C8 46.9(2) . . . . ?
C11 C10 C9 C8 -67.71(19) . . . . ?
C1 C11 C12 O12 -32.7(2) . . . . ?
C18 C11 C12 O12 84.2(2) . . . . ?
C10 C11 C12 O12 -162.19(16) . . . . ?
C1 C11 C12 C13 152.11(15) . . . . ?
C18 C11 C12 C13 -90.91(15) . . . . ?
C10 C11 C12 C13 22.67(17) . . . . ?
C15 C14 C13 C12 170.45(16) . . . . ?
C10 C14 C13 C12 -7.8(2) . . . . ?
O12 C12 C13 C14 174.65(17) . . . . ?
C11 C12 C13 C14 -10.3(2) . . . . ?
C2 C6 C5 C4 -19.19(18) . . . . ?
C7 C6 C5 C4 -149.75(15) . . . . ?
C6 C5 C4 C3 35.81(18) . . . . ?
O3 C3 C4 C5 -159.13(14) . . . . ?
C16 C3 C4 C5 81.44(18) . . . . ?
C2 C3 C4 C5 -37.27(17) . . . . ?
C41 C23 C24 C36 41.2(3) . . . . ?
C22 C23 C24 C36 -82.1(2) . . . . ?
C41 C23 C24 C25 -135.70(16) . . . . ?
C22 C23 C24 C25 101.01(18) . . . . ?
C36 C24 C25 O9 140.15(15) . . . . ?
C23 C24 C25 O9 -42.5(2) . . . . ?
C36 C24 C25 C37 -101.52(17) . . . . ?
C23 C24 C25 C37 75.85(19) . . . . ?
C36 C24 C25 C26 19.92(18) . . . . ?
C23 C24 C25 C26 -162.71(15) . . . . ?
O9 C25 C26 C27 89.70(18) . . . . ?
C24 C25 C26 C27 -152.06(14) . . . . ?
C37 C25 C26 C27 -33.4(2) . . . . ?
O9 C25 C26 C35 -142.95(14) . . . . ?
C24 C25 C26 C35 -24.71(16) . . . . ?
C37 C25 C26 C35 93.96(15) . . . . ?
O9 C25 C26 C42 -34.49(18) . . . . ?
C24 C25 C26 C42 83.75(16) . . . . ?
C37 C25 C26 C42 -157.58(14) . . . . ?
C35 C26 C27 C28 -45.7(3) . . . . ?
C42 C26 C27 C28 -160.62(18) . . . . ?
C25 C26 C27 C28 74.9(2) . . . . ?
C26 C27 C28 C34 -1.3(3) . . . . ?
C26 C27 C28 C29 166.57(16) . . . . ?
C27 C28 C29 O7 -23.8(2) . . . . ?
C34 C28 C29 O7 146.47(13) . . . . ?
C27 C28 C29 C30 93.95(18) . . . . ?
C34 C28 C29 C30 -95.75(16) . . . . ?
C27 C28 C29 C32 -145.09(15) . . . . ?
C34 C28 C29 C32 25.21(17) . . . . ?
C31 O6 C30 C29 172.21(16) . . . . ?
O7 C29 C30 O6 -62.47(17) . . . . ?
C32 C29 C30 O6 60.78(19) . . . . ?
C28 C29 C30 O6 174.83(14) . . . . ?
O7 C29 C32 C33 -157.97(14) . . . . ?
C30 C29 C32 C33 82.88(18) . . . . ?
C28 C29 C32 C33 -36.07(17) . . . . ?
C29 C32 C33 C34 34.39(18) . . . . ?
C27 C28 C34 C33 164.06(17) . . . . ?
C29 C28 C34 C33 -4.68(17) . . . . ?
C27 C28 C34 C39 -70.4(2) . . . . ?
C29 C28 C34 C39 120.88(16) . . . . ?
C32 C33 C34 C28 -18.14(18) . . . . ?
C32 C33 C34 C39 -148.60(14) . . . . ?
C27 C26 C35 O1 -32.0(2) . . . . ?
C42 C26 C35 O1 85.9(2) . . . . ?
C25 C26 C35 O1 -161.14(16) . . . . ?
C27 C26 C35 C36 151.90(14) . . . . ?
C42 C26 C35 C36 -90.26(15) . . . . ?
C25 C26 C35 C36 22.71(17) . . . . ?
C23 C24 C36 C35 177.16(16) . . . . ?
C25 C24 C36 C35 -5.7(2) . . . . ?
O1 C35 C36 C24 172.44(18) . . . . ?
C26 C35 C36 C24 -11.55(19) . . . . ?
O9 C25 C37 C38 170.11(14) . . . . ?
C24 C25 C37 C38 50.48(19) . . . . ?
C26 C25 C37 C38 -64.1(2) . . . . ?
C25 C37 C38 O2 -123.53(15) . . . . ?
C25 C37 C38 C39 113.87(16) . . . . ?
O2 C38 C39 C40 -65.03(18) . . . . ?
C37 C38 C39 C40 54.87(19) . . . . ?
O2 C38 C39 C34 164.08(13) . . . . ?
C37 C38 C39 C34 -76.02(18) . . . . ?
C28 C34 C39 C40 -60.6(2) . . . . ?
C33 C34 C39 C40 61.51(19) . . . . ?
C28 C34 C39 C38 68.1(2) . . . . ?
C33 C34 C39 C38 -169.81(14) . . . . ?
C43 C44 C45 C54 42.7(3) . . . . ?
C53 C44 C45 C54 -80.8(2) . . . . ?
C43 C44 C45 C46 -134.11(17) . . . . ?
C53 C44 C45 C46 102.38(19) . . . . ?
C54 C45 C46 O13 141.08(15) . . . . ?
C44 C45 C46 O13 -41.6(2) . . . . ?
C54 C45 C46 C56 -100.39(17) . . . . ?
C44 C45 C46 C56 76.92(19) . . . . ?
C54 C45 C46 C47 20.45(19) . . . . ?
C44 C45 C46 C47 -162.24(15) . . . . ?
O13 C46 C47 C48 88.97(18) . . . . ?
C45 C46 C47 C48 -152.69(15) . . . . ?
C56 C46 C47 C48 -33.5(2) . . . . ?
O13 C46 C47 C55 -143.69(14) . . . . ?
C45 C46 C47 C55 -25.34(16) . . . . ?
C56 C46 C47 C55 93.80(16) . . . . ?
O13 C46 C47 C63 -34.81(19) . . . . ?
C45 C46 C47 C63 83.53(16) . . . . ?
C56 C46 C47 C63 -157.33(14) . . . . ?
C55 C47 C48 C49 -46.0(3) . . . . ?
C63 C47 C48 C49 -161.51(18) . . . . ?
C46 C47 C48 C49 74.4(2) . . . . ?
C47 C48 C49 C59 -2.1(3) . . . . ?
C47 C48 C49 C50 167.45(16) . . . . ?
C48 C49 C50 O4 -28.0(2) . . . . ?
C59 C49 C50 O4 143.80(14) . . . . ?
C48 C49 C50 C51 89.51(18) . . . . ?
C59 C49 C50 C51 -98.65(16) . . . . ?
C48 C49 C50 C61 -149.58(16) . . . . ?
C59 C49 C50 C61 22.25(17) . . . . ?
C52 O11 C51 C50 172.04(15) . . . . ?
O4 C50 C51 O11 -63.33(17) . . . . ?
C61 C50 C51 O11 59.93(19) . . . . ?
C49 C50 C51 O11 174.37(14) . . . . ?
C44 C45 C54 C55 177.09(16) . . . . ?
C46 C45 C54 C55 -5.8(2) . . . . ?
C45 C54 C55 O14 171.43(17) . . . . ?
C45 C54 C55 C47 -11.9(2) . . . . ?
C48 C47 C55 O14 -30.5(2) . . . . ?
C63 C47 C55 O14 87.5(2) . . . . ?
C46 C47 C55 O14 -159.91(16) . . . . ?
C48 C47 C55 C54 152.70(15) . . . . ?
C63 C47 C55 C54 -89.34(16) . . . . ?
C46 C47 C55 C54 23.28(17) . . . . ?
O13 C46 C56 C57 171.87(14) . . . . ?
C45 C46 C56 C57 52.1(2) . . . . ?
C47 C46 C56 C57 -62.7(2) . . . . ?
C46 C56 C57 O15 -120.40(16) . . . . ?
C46 C56 C57 C58 117.18(17) . . . . ?
O15 C57 C58 C62 -67.72(18) . . . . ?
C56 C57 C58 C62 51.7(2) . . . . ?
O15 C57 C58 C59 161.38(14) . . . . ?
C56 C57 C58 C59 -79.15(18) . . . . ?
C48 C49 C59 C60 169.19(19) . . . . ?
C50 C49 C59 C60 -1.07(18) . . . . ?
C48 C49 C59 C58 -65.7(3) . . . . ?
C50 C49 C59 C58 124.06(16) . . . . ?
C57 C58 C59 C49 65.3(2) . . . . ?
C62 C58 C59 C49 -63.6(2) . . . . ?
C57 C58 C59 C60 -173.06(15) . . . . ?
C62 C58 C59 C60 58.1(2) . . . . ?
C49 C59 C60 C61 -20.85(19) . . . . ?
C58 C59 C60 C61 -150.83(15) . . . . ?
C59 C60 C61 C50 35.36(19) . . . . ?
O4 C50 C61 C60 -157.07(15) . . . . ?
C51 C50 C61 C60 83.56(18) . . . . ?
C49 C50 C61 C60 -34.93(18) . . . . ?

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
C54 H54 O8 0.95 2.43 3.336(2) 159.3 2_457
C36 H36 O15 0.95 2.54 3.424(2) 155.6 2_556
C13 H13A O2 0.95 2.46 3.364(2) 159.2 4_655
O15 H15 O4 0.84 2.04 2.8632(18) 168.3 1_455
O13 H13 O1 0.84 2.08 2.8962(18) 165.6 2_556
O4 H4 O10 0.84 2.07 2.8834(17) 164.6 2_557
O2 H2 O7 0.84 2.00 2.8315(17) 168.8 1_655
O9 H9 O12 0.84 2.06 2.8769(18) 164.0 4_554
O7 H7 O13 0.84 2.01 2.8157(17) 161.9 2_456
O10 H10 O14 0.84 2.04 2.8528(18) 163.2 2_457
O8 H8 O3 0.84 2.01 2.8357(17) 167.9 1_655
O3 H3 O9 0.84 2.01 2.8312(17) 165.7 4
C54 H54 O8 0.95 2.43 3.336(2) 159.3 2_457
C36 H36 O15 0.95 2.54 3.424(2) 155.6 2_556
C13 H13A O2 0.95 2.46 3.364(2) 159.2 4_655
O15 H15 O4 0.84 2.04 2.8632(18) 168.3 1_455
O13 H13 O1 0.84 2.08 2.8962(18) 165.6 2_556
O4 H4 O10 0.84 2.07 2.8834(17) 164.6 2_557
O2 H2 O7 0.84 2.00 2.8315(17) 168.8 1_655
O9 H9 O12 0.84 2.06 2.8769(18) 164.0 4_554
O7 H7 O13 0.84 2.01 2.8157(17) 161.9 2_456
O10 H10 O14 0.84 2.04 2.8528(18) 163.2 2_457
O8 H8 O3 0.84 2.01 2.8357(17) 167.9 1_655
O3 H3 O9 0.84 2.01 2.8312(17) 165.7 4
C54 H54 O8 0.95 2.43 3.336(2) 159.3 2_457
C36 H36 O15 0.95 2.54 3.424(2) 155.6 2_556
C13 H13A O2 0.95 2.46 3.364(2) 159.2 4_655
O15 H15 O4 0.84 2.04 2.8632(18) 168.3 1_455
O13 H13 O1 0.84 2.08 2.8962(18) 165.6 2_556
O4 H4 O10 0.84 2.07 2.8834(17) 164.6 2_557
O2 H2 O7 0.84 2.00 2.8315(17) 168.8 1_655
O9 H9 O12 0.84 2.06 2.8769(18) 164.0 4_554
O7 H7 O13 0.84 2.01 2.8157(17) 161.9 2_456
O10 H10 O14 0.84 2.04 2.8528(18) 163.2 2_457
O8 H8 O3 0.84 2.01 2.8357(17) 167.9 1_655
O3 H3 O9 0.84 2.01 2.8312(17) 165.7 4
C54 H54 O8 0.95 2.43 3.336(2) 159.3 2_457
C36 H36 O15 0.95 2.54 3.424(2) 155.6 2_556
C13 H13A O2 0.95 2.46 3.364(2) 159.2 4_655
O15 H15 O4 0.84 2.04 2.8632(18) 168.3 1_455
O13 H13 O1 0.84 2.08 2.8962(18) 165.6 2_556
O4 H4 O10 0.84 2.07 2.8834(17) 164.6 2_557
O2 H2 O7 0.84 2.00 2.8315(17) 168.8 1_655
O9 H9 O12 0.84 2.06 2.8769(18) 164.0 4_554
O7 H7 O13 0.84 2.01 2.8157(17) 161.9 2_456
O10 H10 O14 0.84 2.04 2.8528(18) 163.2 2_457
O8 H8 O3 0.84 2.01 2.8357(17) 167.9 1_655
O3 H3 O9 0.84 2.01 2.8312(17) 165.7 4
O3 H3 O9 0.84 2.01 2.8312(17) 165.7 4
O8 H8 O3 0.84 2.01 2.8357(17) 167.9 1_655
O10 H10 O14 0.84 2.04 2.8528(18) 163.2 2_457
O7 H7 O13 0.84 2.01 2.8157(17) 161.9 2_456
O9 H9 O12 0.84 2.06 2.8769(18) 164.0 4_554
O2 H2 O7 0.84 2.00 2.8315(17) 168.8 1_655
O4 H4 O10 0.84 2.07 2.8834(17) 164.6 2_557
O13 H13 O1 0.84 2.08 2.8962(18) 165.6 2_556
O15 H15 O4 0.84 2.04 2.8632(18) 168.3 1_455
C13 H13A O2 0.95 2.46 3.364(2) 159.2 4_655
C36 H36 O15 0.95 2.54 3.424(2) 155.6 2_556
C54 H54 O8 0.95 2.43 3.336(2) 159.3 2_457
O3 H3 O9 0.84 2.01 2.8312(17) 165.7 4
O8 H8 O3 0.84 2.01 2.8357(17) 167.9 1_655
O10 H10 O14 0.84 2.04 2.8528(18) 163.2 2_457
O7 H7 O13 0.84 2.01 2.8157(17) 161.9 2_456
O9 H9 O12 0.84 2.06 2.8769(18) 164.0 4_554
O2 H2 O7 0.84 2.00 2.8315(17) 168.8 1_655
O4 H4 O10 0.84 2.07 2.8834(17) 164.6 2_557
O13 H13 O1 0.84 2.08 2.8962(18) 165.6 2_556
O15 H15 O4 0.84 2.04 2.8632(18) 168.3 1_455
C13 H13A O2 0.95 2.46 3.364(2) 159.2 4_655
C36 H36 O15 0.95 2.54 3.424(2) 155.6 2_556
C54 H54 O8 0.95 2.43 3.336(2) 159.3 2_457
O3 H3 O9 0.84 2.01 2.8312(17) 165.7 4
O8 H8 O3 0.84 2.01 2.8357(17) 167.9 1_655
O10 H10 O14 0.84 2.04 2.8528(18) 163.2 2_457
O7 H7 O13 0.84 2.01 2.8157(17) 161.9 2_456
O9 H9 O12 0.84 2.06 2.8769(18) 164.0 4_554
O2 H2 O7 0.84 2.00 2.8315(17) 168.8 1_655
O4 H4 O10 0.84 2.07 2.8834(17) 164.6 2_557
O13 H13 O1 0.84 2.08 2.8962(18) 165.6 2_556
O15 H15 O4 0.84 2.04 2.8632(18) 168.3 1_455
C13 H13A O2 0.95 2.46 3.364(2) 159.2 4_655
C36 H36 O15 0.95 2.54 3.424(2) 155.6 2_556
C54 H54 O8 0.95 2.43 3.336(2) 159.3 2_457

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.261
_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_cu_zyh_lyy3262_0m
_database_code_depnum_ccdc_archive 'CCDC 1860579'
_audit_update_record             
;
2018-08-07 deposited with the CCDC.
2018-10-18 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         'C21 H32 O5'
_chemical_formula_sum            'C21 H32 O5'
_chemical_formula_weight         364.46

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                   6.3056(2)
_cell_length_b                   17.1631(6)
_cell_length_c                   17.9081(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.5190(10)
_cell_angle_gamma                90
_cell_volume                     1936.21(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      69.71

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   0.4258
_exptl_transmission_factor_max   0.7533
_exptl_crystal_size_max          1.050
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.708
_shelx_estimated_absorpt_T_min   0.523
_shelx_estimated_absorpt_T_max   0.901
_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            15901
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.568
_diffrn_reflns_theta_max         70.267
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_point_group_measured_fraction_full 0.863
_reflns_number_total             6140
_reflns_number_gt                5897
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.704
_reflns_Friedel_fraction_full    0.739

_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)+(0.1667P)²] 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 2223 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6140
_refine_ls_number_parameters     485
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.2013
_refine_ls_wR_factor_gt          0.1996
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.010
_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
O16 O 0.8006(4) -0.15255(17) 0.59938(17) 0.0151(6) Uani 1 1 d . . . . .
O3 O 1.0650(5) -0.05804(17) 0.69934(16) 0.0161(6) Uani 1 1 d . . . . .
H3 H 1.0791 -0.1067 0.6990 0.024 Uiso 1 1 calc R U . . .
O12 O 0.9079(5) 0.16864(19) 0.84356(16) 0.0176(7) Uani 1 1 d . . . . .
H12 H 0.9888 0.1355 0.8643 0.026 Uiso 1 1 calc R U . . .
O13 O 1.0997(5) 0.3187(2) 0.81438(17) 0.0229(7) Uani 1 1 d . . . . .
O8 O 0.8951(5) 0.24652(19) 0.44328(16) 0.0162(6) Uani 1 1 d . . . . .
H8 H 0.9614 0.2875 0.4337 0.024 Uiso 1 1 calc R U . . .
O16' O 0.4206(5) 0.64380(18) 0.69403(17) 0.0182(7) Uani 1 1 d . . . . .
O3' O 0.1906(5) 0.77959(19) 0.71120(16) 0.0164(6) Uani 1 1 d . . . . .
H3' H 0.2351 0.8256 0.7153 0.025 Uiso 1 1 calc R U . . .
O13' O 0.1569(5) 1.08965(19) 0.94130(16) 0.0181(7) Uani 1 1 d . . . . .
O12' O 0.3043(5) 1.03334(18) 0.80049(16) 0.0163(6) Uani 1 1 d . . . . .
H12' H 0.2906 1.0798 0.8141 0.024 Uiso 1 1 calc R U . . .
O8' O 0.4189(5) 0.75000(19) 1.09601(16) 0.0191(7) Uani 1 1 d . . . . .
H8' H 0.3377 0.7137 1.1079 0.029 Uiso 1 1 calc R U . . .
C20 C 0.9523(8) 0.4370(3) 0.6825(3) 0.0258(10) Uani 1 1 d . . . . .
H20A H 0.7996 0.4297 0.6724 0.039 Uiso 1 1 calc R U . . .
H20B H 0.9975 0.4858 0.6597 0.039 Uiso 1 1 calc R U . . .
H20C H 0.9823 0.4392 0.7366 0.039 Uiso 1 1 calc R U . . .
C15 C 1.0742(6) 0.3682(3) 0.6492(2) 0.0167(9) Uani 1 1 d . . . . .
H15 H 1.0377 0.3659 0.5943 0.020 Uiso 1 1 calc R U . . .
C14 C 1.0037(6) 0.2928(2) 0.6842(2) 0.0133(8) Uani 1 1 d . . . . .
C10 C 0.8871(6) 0.2354(2) 0.6525(2) 0.0111(8) Uani 1 1 d . . . . .
C11 C 0.8256(6) 0.1728(2) 0.7072(2) 0.0123(8) Uani 1 1 d . . . . .
C1 C 0.8401(6) 0.0890(2) 0.6832(2) 0.0119(8) Uani 1 1 d . . . . .
H1 H 0.7498 0.0540 0.7079 0.014 Uiso 1 1 calc R U . . .
C2 C 0.9613(6) 0.0567(3) 0.6323(2) 0.0122(8) Uani 1 1 d . . . . .
C3 C 0.9809(6) -0.0324(3) 0.6275(2) 0.0115(8) Uani 1 1 d . . . . .
C16 C 0.7701(6) -0.0713(2) 0.6096(2) 0.0126(8) Uani 1 1 d . . . . .
H16A H 0.6738 -0.0625 0.6510 0.015 Uiso 1 1 calc R U . . .
H16B H 0.7036 -0.0484 0.5635 0.015 Uiso 1 1 calc R U . . .
C21 C 0.6053(6) -0.1921(3) 0.5831(2) 0.0182(9) Uani 1 1 d . . . . .
H21A H 0.5131 -0.1867 0.6255 0.027 Uiso 1 1 calc R U . . .
H21B H 0.6335 -0.2475 0.5745 0.027 Uiso 1 1 calc R U . . .
H21C H 0.5351 -0.1694 0.5383 0.027 Uiso 1 1 calc R U . . .
C4 C 1.1450(6) -0.0455(3) 0.5670(2) 0.0153(8) Uani 1 1 d . . . . .
H4A H 1.2356 -0.0913 0.5793 0.018 Uiso 1 1 calc R U . . .
H4B H 1.0736 -0.0535 0.5173 0.018 Uiso 1 1 calc R U . . .
C5 C 1.2763(6) 0.0296(3) 0.5686(2) 0.0172(9) Uani 1 1 d . . . . .
H5A H 1.3462 0.0371 0.5207 0.021 Uiso 1 1 calc R U . . .
H5B H 1.3866 0.0282 0.6097 0.021 Uiso 1 1 calc R U . . .
C6 C 1.1150(6) 0.0958(2) 0.5814(2) 0.0119(8) Uani 1 1 d . . . . .
H6 H 1.1898 0.1383 0.6101 0.014 Uiso 1 1 calc R U . . .
C18 C 0.5957(6) 0.1892(3) 0.7302(2) 0.0143(8) Uani 1 1 d . . . . .
H18A H 0.4984 0.1853 0.6862 0.022 Uiso 1 1 calc R U . . .
H18B H 0.5879 0.2417 0.7514 0.022 Uiso 1 1 calc R U . . .
H18C H 0.5554 0.1508 0.7676 0.022 Uiso 1 1 calc R U . . .
C12 C 0.9850(6) 0.1887(3) 0.7737(2) 0.0138(8) Uani 1 1 d . . . . .
H12A H 1.1161 0.1575 0.7660 0.017 Uiso 1 1 calc R U . . .
C13 C 1.0402(6) 0.2750(3) 0.7652(2) 0.0152(8) Uani 1 1 d . . . . .
C9 C 0.8004(6) 0.2358(2) 0.5726(2) 0.0130(8) Uani 1 1 d . . . . .
H9A H 0.7390 0.2877 0.5611 0.016 Uiso 1 1 calc R U . . .
H9B H 0.6843 0.1971 0.5673 0.016 Uiso 1 1 calc R U . . .
C8 C 0.9683(6) 0.2170(3) 0.5151(2) 0.0120(8) Uani 1 1 d . . . . .
H8A H 1.1024 0.2449 0.5305 0.014 Uiso 1 1 calc R U . . .
C7 C 1.0191(6) 0.1309(3) 0.5070(2) 0.0135(8) Uani 1 1 d . . . . .
H7 H 1.1339 0.1278 0.4703 0.016 Uiso 1 1 calc R U . . .
C17 C 0.8296(7) 0.0861(3) 0.4718(2) 0.0190(9) Uani 1 1 d . . . . .
H17A H 0.7153 0.0842 0.5071 0.029 Uiso 1 1 calc R U . . .
H17B H 0.8736 0.0330 0.4599 0.029 Uiso 1 1 calc R U . . .
H17C H 0.7787 0.1125 0.4259 0.029 Uiso 1 1 calc R U . . .
C19 C 1.3141(7) 0.3801(3) 0.6600(3) 0.0301(11) Uani 1 1 d . . . . .
H19A H 1.3525 0.3841 0.7135 0.045 Uiso 1 1 calc R U . . .
H19B H 1.3551 0.4281 0.6348 0.045 Uiso 1 1 calc R U . . .
H19C H 1.3883 0.3358 0.6387 0.045 Uiso 1 1 calc R U . . .
C19' C 0.3941(7) 0.9600(3) 1.1369(2) 0.0241(10) Uani 1 1 d . . . . .
H19D H 0.3671 0.9039 1.1400 0.036 Uiso 1 1 calc R U . . .
H19E H 0.3616 0.9848 1.1844 0.036 Uiso 1 1 calc R U . . .
H19F H 0.5437 0.9688 1.1268 0.036 Uiso 1 1 calc R U . . .
C15' C 0.2538(7) 0.9951(3) 1.0739(2) 0.0183(9) Uani 1 1 d . . . . .
H15' H 0.2728 1.0528 1.0778 0.022 Uiso 1 1 calc R U . . .
C14' C 0.3099(6) 0.9736(2) 0.9951(2) 0.0121(8) Uani 1 1 d . . . . .
C10' C 0.4177(6) 0.9132(2) 0.9660(2) 0.0122(8) Uani 1 1 d . . . . .
C11' C 0.4478(6) 0.9245(2) 0.8824(2) 0.0112(8) Uani 1 1 d . . . . .
C1' C 0.4258(6) 0.8534(3) 0.8337(2) 0.0124(8) Uani 1 1 d . . . . .
H1' H 0.5144 0.8521 0.7922 0.015 Uiso 1 1 calc R U . . .
C2' C 0.2997(6) 0.7920(2) 0.8406(2) 0.0113(8) Uani 1 1 d . . . . .
C3' C 0.2655(6) 0.7347(2) 0.7755(2) 0.0140(9) Uani 1 1 d . . . . .
C16' C 0.4695(7) 0.6935(2) 0.7561(2) 0.0140(8) Uani 1 1 d . . . . .
H16C H 0.5785 0.7321 0.7430 0.017 Uiso 1 1 calc R U . . .
H16D H 0.5251 0.6625 0.7993 0.017 Uiso 1 1 calc R U . . .
C21' C 0.6007(7) 0.6013(3) 0.6733(2) 0.0206(9) Uani 1 1 d . . . . .
H21D H 0.7095 0.6375 0.6568 0.031 Uiso 1 1 calc R U . . .
H21E H 0.5604 0.5656 0.6324 0.031 Uiso 1 1 calc R U . . .
H21F H 0.6573 0.5714 0.7163 0.031 Uiso 1 1 calc R U . . .
C20' C 0.0169(7) 0.9797(3) 1.0851(3) 0.0219(10) Uani 1 1 d . . . . .
H20D H -0.0684 1.0047 1.0448 0.033 Uiso 1 1 calc R U . . .
H20E H -0.0221 1.0011 1.1333 0.033 Uiso 1 1 calc R U . . .
H20F H -0.0096 0.9234 1.0843 0.033 Uiso 1 1 calc R U . . .
C13' C 0.2368(6) 1.0260(3) 0.9345(2) 0.0127(8) Uani 1 1 d . . . . .
C12' C 0.2694(6) 0.9833(2) 0.8613(2) 0.0127(8) Uani 1 1 d . . . . .
H12B H 0.1375 0.9528 0.8487 0.015 Uiso 1 1 calc R U . . .
C9' C 0.5077(6) 0.8434(2) 1.0054(2) 0.0116(8) Uani 1 1 d . . . . .
H9'1 H 0.5972 0.8605 1.0492 0.014 Uiso 1 1 calc R U . . .
H9'2 H 0.5992 0.8146 0.9714 0.014 Uiso 1 1 calc R U . . .
C8' C 0.3315(6) 0.7888(3) 1.0317(2) 0.0138(8) Uani 1 1 d . . . . .
H8'1 H 0.2108 0.8218 1.0476 0.017 Uiso 1 1 calc R U . . .
C7' C 0.2442(6) 0.7307(3) 0.9727(2) 0.0154(9) Uani 1 1 d . . . . .
H7' H 0.1233 0.7035 0.9959 0.018 Uiso 1 1 calc R U . . .
C6' C 0.1462(6) 0.7735(3) 0.9020(2) 0.0129(8) Uani 1 1 d . . . . .
H6' H 0.0798 0.8232 0.9184 0.015 Uiso 1 1 calc R U . . .
C5' C -0.0242(6) 0.7243(3) 0.8600(2) 0.0189(9) Uani 1 1 d . . . . .
H5'1 H -0.0923 0.6880 0.8947 0.023 Uiso 1 1 calc R U . . .
H5'2 H -0.1350 0.7582 0.8364 0.023 Uiso 1 1 calc R U . . .
C4' C 0.0916(7) 0.6792(3) 0.8008(3) 0.0187(9) Uani 1 1 d . . . . .
H4'1 H -0.0068 0.6654 0.7582 0.022 Uiso 1 1 calc R U . . .
H4'2 H 0.1547 0.6308 0.8221 0.022 Uiso 1 1 calc R U . . .
C17' C 0.4072(7) 0.6676(3) 0.9574(3) 0.0195(9) Uani 1 1 d . . . . .
H17D H 0.5237 0.6902 0.9301 0.029 Uiso 1 1 calc R U . . .
H17E H 0.3393 0.6260 0.9273 0.029 Uiso 1 1 calc R U . . .
H17F H 0.4634 0.6460 1.0049 0.029 Uiso 1 1 calc R U . . .
C18' C 0.6686(6) 0.9617(3) 0.8733(2) 0.0160(8) Uani 1 1 d . . . . .
H18D H 0.7788 0.9264 0.8936 0.024 Uiso 1 1 calc R U . . .
H18E H 0.6767 1.0113 0.9004 0.024 Uiso 1 1 calc R U . . .
H18F H 0.6902 0.9709 0.8202 0.024 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
O16 C16 1.421(5) . ?
O16 C21 1.425(5) . ?
O3 C3 1.440(5) . ?
O3 H3 0.8400 . ?
O12 C12 1.404(5) . ?
O12 H12 0.8400 . ?
O13 C13 1.204(6) . ?
O8 C8 1.440(5) . ?
O8 H8 0.8400 . ?
O16' C21' 1.413(5) . ?
O16' C16' 1.424(5) . ?
O3' C3' 1.447(5) . ?
O3' H3' 0.8400 . ?
O13' C13' 1.212(5) . ?
O12' C12' 1.411(5) . ?
O12' H12' 0.8400 . ?
O8' C8' 1.420(5) . ?
O8' H8' 0.8400 . ?
C20 C15 1.543(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C15 C14 1.513(6) . ?
C15 C19 1.530(6) . ?
C15 H15 1.0000 . ?
C14 C10 1.340(6) . ?
C14 C13 1.491(5) . ?
C10 C9 1.509(5) . ?
C10 C11 1.517(5) . ?
C11 C1 1.504(6) . ?
C11 C12 1.549(6) . ?
C11 C18 1.550(5) . ?
C1 C2 1.335(6) . ?
C1 H1 0.9500 . ?
C2 C6 1.516(5) . ?
C2 C3 1.537(6) . ?
C3 C16 1.509(6) . ?
C3 C4 1.546(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C4 C5 1.532(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.548(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.560(5) . ?
C6 H6 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C12 C13 1.530(6) . ?
C12 H12A 1.0000 . ?
C9 C8 1.543(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8 C7 1.520(6) . ?
C8 H8A 1.0000 . ?
C7 C17 1.533(6) . ?
C7 H7 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19' C15' 1.527(6) . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?
C15' C14' 1.515(5) . ?
C15' C20' 1.539(6) . ?
C15' H15' 1.0000 . ?
C14' C10' 1.357(6) . ?
C14' C13' 1.467(6) . ?
C10' C9' 1.489(6) . ?
C10' C11' 1.529(5) . ?
C11' C1' 1.505(6) . ?
C11' C12' 1.546(6) . ?
C11' C18' 1.546(5) . ?
C1' C2' 1.328(6) . ?
C1' H1' 0.9500 . ?
C2' C6' 1.530(5) . ?
C2' C3' 1.534(6) . ?
C3' C16' 1.522(6) . ?
C3' C4' 1.536(6) . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C21' H21D 0.9800 . ?
C21' H21E 0.9800 . ?
C21' H21F 0.9800 . ?
C20' H20D 0.9800 . ?
C20' H20E 0.9800 . ?
C20' H20F 0.9800 . ?
C13' C12' 1.525(5) . ?
C12' H12B 1.0000 . ?
C9' C8' 1.544(5) . ?
C9' H9'1 0.9900 . ?
C9' H9'2 0.9900 . ?
C8' C7' 1.537(6) . ?
C8' H8'1 1.0000 . ?
C7' C17' 1.527(6) . ?
C7' C6' 1.566(5) . ?
C7' H7' 1.0000 . ?
C6' C5' 1.537(6) . ?
C6' H6' 1.0000 . ?
C5' C4' 1.525(6) . ?
C5' H5'1 0.9900 . ?
C5' H5'2 0.9900 . ?
C4' H4'1 0.9900 . ?
C4' H4'2 0.9900 . ?
C17' H17D 0.9800 . ?
C17' H17E 0.9800 . ?
C17' H17F 0.9800 . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 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
C16 O16 C21 111.9(3) . . ?
C3 O3 H3 109.5 . . ?
C12 O12 H12 109.5 . . ?
C8 O8 H8 109.5 . . ?
C21' O16' C16' 111.4(3) . . ?
C3' O3' H3' 109.5 . . ?
C12' O12' H12' 109.5 . . ?
C8' O8' H8' 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C15 C19 111.6(4) . . ?
C14 C15 C20 109.5(3) . . ?
C19 C15 C20 110.8(4) . . ?
C14 C15 H15 108.3 . . ?
C19 C15 H15 108.3 . . ?
C20 C15 H15 108.3 . . ?
C10 C14 C13 108.7(4) . . ?
C10 C14 C15 128.2(4) . . ?
C13 C14 C15 122.9(4) . . ?
C14 C10 C9 124.6(4) . . ?
C14 C10 C11 113.5(3) . . ?
C9 C10 C11 121.6(3) . . ?
C1 C11 C10 118.2(3) . . ?
C1 C11 C12 110.1(3) . . ?
C10 C11 C12 101.3(3) . . ?
C1 C11 C18 108.6(3) . . ?
C10 C11 C18 108.2(3) . . ?
C12 C11 C18 110.3(3) . . ?
C2 C1 C11 129.5(4) . . ?
C2 C1 H1 115.2 . . ?
C11 C1 H1 115.2 . . ?
C1 C2 C6 128.8(4) . . ?
C1 C2 C3 120.2(4) . . ?
C6 C2 C3 110.5(3) . . ?
O3 C3 C16 109.9(3) . . ?
O3 C3 C2 106.3(3) . . ?
C16 C3 C2 112.3(3) . . ?
O3 C3 C4 110.5(3) . . ?
C16 C3 C4 113.4(3) . . ?
C2 C3 C4 104.1(3) . . ?
O16 C16 C3 109.8(3) . . ?
O16 C16 H16A 109.7 . . ?
C3 C16 H16A 109.7 . . ?
O16 C16 H16B 109.7 . . ?
C3 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
O16 C21 H21A 109.5 . . ?
O16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 C4 C3 104.0(3) . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C4 C5 C6 105.2(3) . . ?
C4 C5 H5A 110.7 . . ?
C6 C5 H5A 110.7 . . ?
C4 C5 H5B 110.7 . . ?
C6 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
C2 C6 C5 101.9(3) . . ?
C2 C6 C7 116.8(3) . . ?
C5 C6 C7 112.9(3) . . ?
C2 C6 H6 108.3 . . ?
C5 C6 H6 108.3 . . ?
C7 C6 H6 108.3 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O12 C12 C13 114.5(3) . . ?
O12 C12 C11 113.8(3) . . ?
C13 C12 C11 103.7(3) . . ?
O12 C12 H12A 108.2 . . ?
C13 C12 H12A 108.2 . . ?
C11 C12 H12A 108.2 . . ?
O13 C13 C14 127.8(4) . . ?
O13 C13 C12 126.5(4) . . ?
C14 C13 C12 105.6(3) . . ?
C10 C9 C8 113.6(3) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O8 C8 C7 108.5(3) . . ?
O8 C8 C9 108.7(3) . . ?
C7 C8 C9 114.9(3) . . ?
O8 C8 H8A 108.2 . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8A 108.2 . . ?
C8 C7 C17 111.3(3) . . ?
C8 C7 C6 111.7(3) . . ?
C17 C7 C6 115.0(3) . . ?
C8 C7 H7 106.0 . . ?
C17 C7 H7 106.0 . . ?
C6 C7 H7 106.0 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15' C19' H19D 109.5 . . ?
C15' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
C15' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
C14' C15' C19' 116.2(4) . . ?
C14' C15' C20' 110.3(4) . . ?
C19' C15' C20' 111.7(4) . . ?
C14' C15' H15' 106.0 . . ?
C19' C15' H15' 106.0 . . ?
C20' C15' H15' 106.0 . . ?
C10' C14' C13' 109.3(3) . . ?
C10' C14' C15' 133.3(4) . . ?
C13' C14' C15' 117.4(4) . . ?
C14' C10' C9' 128.2(4) . . ?
C14' C10' C11' 111.4(4) . . ?
C9' C10' C11' 120.4(4) . . ?
C1' C11' C10' 116.9(3) . . ?
C1' C11' C12' 109.9(3) . . ?
C10' C11' C12' 101.7(3) . . ?
C1' C11' C18' 109.5(3) . . ?
C10' C11' C18' 107.9(3) . . ?
C12' C11' C18' 110.8(3) . . ?
C2' C1' C11' 129.0(4) . . ?
C2' C1' H1' 115.5 . . ?
C11' C1' H1' 115.5 . . ?
C1' C2' C6' 129.2(4) . . ?
C1' C2' C3' 120.1(4) . . ?
C6' C2' C3' 109.9(3) . . ?
O3' C3' C16' 108.4(3) . . ?
O3' C3' C2' 107.1(3) . . ?
C16' C3' C2' 112.3(3) . . ?
O3' C3' C4' 110.6(3) . . ?
C16' C3' C4' 113.6(4) . . ?
C2' C3' C4' 104.6(3) . . ?
O16' C16' C3' 107.5(3) . . ?
O16' C16' H16C 110.2 . . ?
C3' C16' H16C 110.2 . . ?
O16' C16' H16D 110.2 . . ?
C3' C16' H16D 110.2 . . ?
H16C C16' H16D 108.5 . . ?
O16' C21' H21D 109.5 . . ?
O16' C21' H21E 109.5 . . ?
H21D C21' H21E 109.5 . . ?
O16' C21' H21F 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
C15' C20' H20D 109.5 . . ?
C15' C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
C15' C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
O13' C13' C14' 126.7(4) . . ?
O13' C13' C12' 126.3(4) . . ?
C14' C13' C12' 107.0(3) . . ?
O12' C12' C13' 113.8(4) . . ?
O12' C12' C11' 116.7(3) . . ?
C13' C12' C11' 103.1(3) . . ?
O12' C12' H12B 107.6 . . ?
C13' C12' H12B 107.6 . . ?
C11' C12' H12B 107.6 . . ?
C10' C9' C8' 111.6(3) . . ?
C10' C9' H9'1 109.3 . . ?
C8' C9' H9'1 109.3 . . ?
C10' C9' H9'2 109.3 . . ?
C8' C9' H9'2 109.3 . . ?
H9'1 C9' H9'2 108.0 . . ?
O8' C8' C7' 111.7(4) . . ?
O8' C8' C9' 105.9(3) . . ?
C7' C8' C9' 115.1(3) . . ?
O8' C8' H8'1 108.0 . . ?
C7' C8' H8'1 108.0 . . ?
C9' C8' H8'1 108.0 . . ?
C17' C7' C8' 111.1(3) . . ?
C17' C7' C6' 115.6(3) . . ?
C8' C7' C6' 111.6(4) . . ?
C17' C7' H7' 105.9 . . ?
C8' C7' H7' 105.9 . . ?
C6' C7' H7' 105.9 . . ?
C2' C6' C5' 102.3(3) . . ?
C2' C6' C7' 116.0(3) . . ?
C5' C6' C7' 112.4(4) . . ?
C2' C6' H6' 108.6 . . ?
C5' C6' H6' 108.6 . . ?
C7' C6' H6' 108.6 . . ?
C4' C5' C6' 105.9(3) . . ?
C4' C5' H5'1 110.6 . . ?
C6' C5' H5'1 110.6 . . ?
C4' C5' H5'2 110.6 . . ?
C6' C5' H5'2 110.6 . . ?
H5'1 C5' H5'2 108.7 . . ?
C5' C4' C3' 105.1(4) . . ?
C5' C4' H4'1 110.7 . . ?
C3' C4' H4'1 110.7 . . ?
C5' C4' H4'2 110.7 . . ?
C3' C4' H4'2 110.7 . . ?
H4'1 C4' H4'2 108.8 . . ?
C7' C17' H17D 109.5 . . ?
C7' C17' H17E 109.5 . . ?
H17D C17' H17E 109.5 . . ?
C7' C17' H17F 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
C11' C18' H18D 109.5 . . ?
C11' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C11' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 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
C19 C15 C14 C10 -127.5(5) . . . . ?
C20 C15 C14 C10 109.4(5) . . . . ?
C19 C15 C14 C13 58.7(5) . . . . ?
C20 C15 C14 C13 -64.4(5) . . . . ?
C13 C14 C10 C9 174.2(3) . . . . ?
C15 C14 C10 C9 -0.2(6) . . . . ?
C13 C14 C10 C11 1.2(4) . . . . ?
C15 C14 C10 C11 -173.2(4) . . . . ?
C14 C10 C11 C1 -137.5(4) . . . . ?
C9 C10 C11 C1 49.3(5) . . . . ?
C14 C10 C11 C12 -17.2(4) . . . . ?
C9 C10 C11 C12 169.5(3) . . . . ?
C14 C10 C11 C18 98.7(4) . . . . ?
C9 C10 C11 C18 -74.5(4) . . . . ?
C10 C11 C1 C2 25.0(6) . . . . ?
C12 C11 C1 C2 -90.7(5) . . . . ?
C18 C11 C1 C2 148.5(4) . . . . ?
C11 C1 C2 C6 -2.6(7) . . . . ?
C11 C1 C2 C3 168.4(4) . . . . ?
C1 C2 C3 O3 -59.2(5) . . . . ?
C6 C2 C3 O3 113.2(3) . . . . ?
C1 C2 C3 C16 61.0(5) . . . . ?
C6 C2 C3 C16 -126.5(3) . . . . ?
C1 C2 C3 C4 -175.9(4) . . . . ?
C6 C2 C3 C4 -3.4(4) . . . . ?
C21 O16 C16 C3 179.4(3) . . . . ?
O3 C3 C16 O16 -66.9(4) . . . . ?
C2 C3 C16 O16 175.0(3) . . . . ?
C4 C3 C16 O16 57.3(4) . . . . ?
O3 C3 C4 C5 -88.7(4) . . . . ?
C16 C3 C4 C5 147.4(3) . . . . ?
C2 C3 C4 C5 25.1(4) . . . . ?
C3 C4 C5 C6 -38.0(4) . . . . ?
C1 C2 C6 C5 152.4(4) . . . . ?
C3 C2 C6 C5 -19.2(4) . . . . ?
C1 C2 C6 C7 -84.0(5) . . . . ?
C3 C2 C6 C7 104.4(4) . . . . ?
C4 C5 C6 C2 34.9(4) . . . . ?
C4 C5 C6 C7 -91.2(4) . . . . ?
C1 C11 C12 O12 -84.0(4) . . . . ?
C10 C11 C12 O12 150.2(3) . . . . ?
C18 C11 C12 O12 35.8(5) . . . . ?
C1 C11 C12 C13 151.0(3) . . . . ?
C10 C11 C12 C13 25.1(3) . . . . ?
C18 C11 C12 C13 -89.3(4) . . . . ?
C10 C14 C13 O13 -163.9(4) . . . . ?
C15 C14 C13 O13 10.9(6) . . . . ?
C10 C14 C13 C12 15.8(4) . . . . ?
C15 C14 C13 C12 -169.4(3) . . . . ?
O12 C12 C13 O13 29.5(6) . . . . ?
C11 C12 C13 O13 154.1(4) . . . . ?
O12 C12 C13 C14 -150.2(3) . . . . ?
C11 C12 C13 C14 -25.6(4) . . . . ?
C14 C10 C9 C8 76.9(5) . . . . ?
C11 C10 C9 C8 -110.7(4) . . . . ?
C10 C9 C8 O8 -158.8(3) . . . . ?
C10 C9 C8 C7 79.5(4) . . . . ?
O8 C8 C7 C17 -54.0(4) . . . . ?
C9 C8 C7 C17 67.8(4) . . . . ?
O8 C8 C7 C6 176.0(3) . . . . ?
C9 C8 C7 C6 -62.2(4) . . . . ?
C2 C6 C7 C8 94.3(4) . . . . ?
C5 C6 C7 C8 -148.0(3) . . . . ?
C2 C6 C7 C17 -33.7(5) . . . . ?
C5 C6 C7 C17 84.0(4) . . . . ?
C19' C15' C14' C10' 22.6(7) . . . . ?
C20' C15' C14' C10' -105.8(5) . . . . ?
C19' C15' C14' C13' -157.9(4) . . . . ?
C20' C15' C14' C13' 73.7(5) . . . . ?
C13' C14' C10' C9' -175.5(4) . . . . ?
C15' C14' C10' C9' 4.0(7) . . . . ?
C13' C14' C10' C11' 6.3(5) . . . . ?
C15' C14' C10' C11' -174.1(4) . . . . ?
C14' C10' C11' C1' -140.8(4) . . . . ?
C9' C10' C11' C1' 40.9(5) . . . . ?
C14' C10' C11' C12' -21.2(4) . . . . ?
C9' C10' C11' C12' 160.4(3) . . . . ?
C14' C10' C11' C18' 95.3(4) . . . . ?
C9' C10' C11' C18' -83.0(4) . . . . ?
C10' C11' C1' C2' 33.5(6) . . . . ?
C12' C11' C1' C2' -81.6(5) . . . . ?
C18' C11' C1' C2' 156.5(4) . . . . ?
C11' C1' C2' C6' -3.0(7) . . . . ?
C11' C1' C2' C3' 166.1(4) . . . . ?
C1' C2' C3' O3' -55.5(5) . . . . ?
C6' C2' C3' O3' 115.6(3) . . . . ?
C1' C2' C3' C16' 63.4(5) . . . . ?
C6' C2' C3' C16' -125.6(4) . . . . ?
C1' C2' C3' C4' -173.0(4) . . . . ?
C6' C2' C3' C4' -1.9(4) . . . . ?
C21' O16' C16' C3' -178.4(4) . . . . ?
O3' C3' C16' O16' -60.2(4) . . . . ?
C2' C3' C16' O16' -178.4(3) . . . . ?
C4' C3' C16' O16' 63.1(4) . . . . ?
C10' C14' C13' O13' -171.1(4) . . . . ?
C15' C14' C13' O13' 9.2(6) . . . . ?
C10' C14' C13' C12' 11.8(4) . . . . ?
C15' C14' C13' C12' -167.8(3) . . . . ?
O13' C13' C12' O12' 31.2(5) . . . . ?
C14' C13' C12' O12' -151.7(3) . . . . ?
O13' C13' C12' C11' 158.6(4) . . . . ?
C14' C13' C12' C11' -24.3(4) . . . . ?
C1' C11' C12' O12' -83.7(4) . . . . ?
C10' C11' C12' O12' 151.9(3) . . . . ?
C18' C11' C12' O12' 37.4(5) . . . . ?
C1' C11' C12' C13' 150.9(3) . . . . ?
C10' C11' C12' C13' 26.4(4) . . . . ?
C18' C11' C12' C13' -88.1(4) . . . . ?
C14' C10' C9' C8' 69.1(5) . . . . ?
C11' C10' C9' C8' -112.9(4) . . . . ?
C10' C9' C8' O8' -151.6(3) . . . . ?
C10' C9' C8' C7' 84.6(4) . . . . ?
O8' C8' C7' C17' -49.7(4) . . . . ?
C9' C8' C7' C17' 71.0(5) . . . . ?
O8' C8' C7' C6' 179.6(3) . . . . ?
C9' C8' C7' C6' -59.7(4) . . . . ?
C1' C2' C6' C5' 151.2(4) . . . . ?
C3' C2' C6' C5' -18.9(4) . . . . ?
C1' C2' C6' C7' -86.1(5) . . . . ?
C3' C2' C6' C7' 103.8(4) . . . . ?
C17' C7' C6' C2' -39.7(5) . . . . ?
C8' C7' C6' C2' 88.6(4) . . . . ?
C17' C7' C6' C5' 77.5(4) . . . . ?
C8' C7' C6' C5' -154.2(3) . . . . ?
C2' C6' C5' C4' 32.8(4) . . . . ?
C7' C6' C5' C4' -92.3(4) . . . . ?
C6' C5' C4' C3' -35.0(5) . . . . ?
O3' C3' C4' C5' -92.7(4) . . . . ?
C16' C3' C4' C5' 145.2(4) . . . . ?
C2' C3' C4' C5' 22.3(4) . . . . ?

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
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
C21 H21A O3' 0.98 2.67 3.586(5) 156.7 1_545
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645
O3 H3 O3' 0.84 2.08 2.902(4) 165.2 1_645
O12 H12 O13' 0.84 1.87 2.670(4) 157.3 1_645
O8 H8 O16 0.84 1.93 2.720(4) 155.2 2_756
O3' H3' O3 0.84 2.28 2.902(4) 131.2 1_465
O12' H12' O13' 0.84 2.47 2.892(4) 112.1 .
O8' H8' O12 0.84 1.97 2.750(4) 154.7 2_657
C12 H12A O12' 1.00 2.50 3.363(5) 143.9 1_645

_refine_diff_density_max         0.714
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.149

####################################################################### 
# 
# 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_20180917_lfl_2-16-3
_database_code_depnum_ccdc_archive 'CCDC 1868981'
_audit_update_record             
;
2018-09-21 deposited with the CCDC.
2018-10-18 downloaded from the CCDC.
;
_audit_creation_date             2018-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H36 O4'
_chemical_formula_sum            'C22 H36 O4'
_chemical_formula_weight         364.51
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.856
_cell_length_b                   15.76930(10)
_cell_length_c                   9.69440(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.6090(10)
_cell_angle_gamma                90
_cell_volume                     1026.588(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    20148
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6800
_cell_measurement_theta_min      4.6410
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22706
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.900
_diffrn_reflns_theta_min         4.656
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  41.00   0.50    0.50    --    0.00  41.00 112.00  118
  2  ω     48.00  87.00   0.50    0.50    --    0.00  41.00 112.00   78
  3  ω    159.00 184.00   0.50    0.50    --   94.60  41.00 112.00   50
  4  ω     38.00  64.00   0.50    0.50    --   94.60 -41.00 -40.00   52
  5  ω     28.00  54.00   0.50    0.50    --    0.00  38.00  60.00   52
  6  ω    -16.00  20.00   0.50    0.50    --    0.00  38.00  60.00   72
  7  ω    -12.00  13.00   0.50    0.50    --    0.00 -77.00  90.00   50
  8  ω    -89.00 -63.00   0.50    0.50    --    0.00 -41.00 -40.00   52
  9  ω    -46.00 -14.00   0.50    0.50    --    0.00 -77.00  90.00   64
 10  ω    -19.00  21.00   0.50    0.50    --    0.00 -57.00-120.00   80
 11  ω     49.00  86.00   0.50    0.50    --    0.00  38.00 -60.00   74
 12  ω    -17.00  86.00   0.50    0.50    --    0.00  38.00-180.00  206
 13  ω    -89.00 -40.00   0.50    0.50    --    0.00 -57.00-120.00   98
 14  ω    -23.00   3.00   0.50    0.50    --    0.00 -41.00 -40.00   52
 15  ω    -17.00  34.00   0.50    0.50    --    0.00  38.00 -60.00  102
 16  ω     -1.00  31.00   0.50    0.50    --    0.00 -82.00  60.00   64
 17  ω     71.00 106.00   0.50    0.50    --   94.60  61.00  30.00   70
 18  ω    141.00 176.00   0.50    0.50    --   94.60  53.00 176.43   70
 19  ω     11.00 126.00   0.50    0.50    --   94.60 -82.00 120.00  230
 20  ω     73.00 137.00   0.50    0.50    --   94.60  53.00 176.43  128
 21  ω    144.00 170.00   0.50    0.50    --   94.60  71.00-136.46   52
 22  ω    146.00 172.00   0.50    0.50    --   94.60  66.00  48.29   52
 23  ω     75.00 139.00   0.50    0.50    --   94.60  45.00 -90.00  128
 24  ω     72.00 102.00   0.50    0.50    --   94.60  57.00 -71.49   60
 25  ω    107.00 184.00   0.50    0.50    --   94.60  64.00 -53.90  154
 26  ω     67.00  95.00   0.50    0.50    --   94.60  71.00-136.46   56
 27  ω      5.00  70.00   0.50    0.50    --   94.60 -82.00   0.00  130
 28  ω     79.00 126.00   0.50    0.50    --   94.60 -82.00   0.00   94
 29  ω     72.00  98.00   0.50    0.50    --   94.60  56.00  80.08   52
 30  ω     72.00 118.00   0.50    0.50    --   94.60  60.00 -13.53   92
 31  ω    123.00 183.00   0.50    0.50    --   94.60  60.00 -13.53  120
 32  ω     74.00  99.00   0.50    0.50    --   94.60  61.00 -30.00   50
 33  ω     71.00 119.00   0.50    0.50    --   94.60  60.00 -68.47   96
 34  ω    139.00 173.00   0.50    0.50    --   94.60  60.00 -68.47   68
 35  ω     71.00  98.00   0.50    0.50    --   94.60  64.00 -53.90   54
 36  ω     72.00  98.00   0.50    0.50    --   94.60  61.00   0.00   52
 37  ω    132.00 158.00   0.50    0.50    --   94.60  71.00 178.94   52
 38  ω     69.00  94.00   0.50    0.50    --   94.60  66.00  48.29   50
 39  ω     78.00 147.00   0.50    0.50    --   94.60  45.00-120.00  138
 40  ω     75.00 184.00   0.50    0.50    --   94.60  45.00 120.00  218
 41  ω     76.00 178.00   0.50    0.50    --   94.60  45.00  60.00  204
 42  ω    132.00 172.00   0.50    0.50    --   94.60  67.00   0.15   80
 43  ω     75.00 111.00   0.50    0.50    --   94.60  45.00  90.00   72
 44  ω     74.00 111.00   0.50    0.50    --   94.60  50.00 -22.59   74
 45  ω     71.00  98.00   0.50    0.50    --   94.60  61.00-150.00   54
 46  ω     71.00  96.00   0.50    0.50    --   94.60  61.00 -90.00   50
 47  ω     72.00  98.00   0.50    0.50    --   94.60  59.00  86.50   52
 48  ω     75.00 151.00   0.50    0.50    --   94.60  49.00-149.69  152
 49  ω     72.00  98.00   0.50    0.50    --   94.60  68.00-156.41   52
 50  ω     73.00 100.00   0.50    0.50    --   94.60  61.00 120.00   54
 51  ω     70.00  96.00   0.50    0.50    --   94.60  64.00 104.35   52
 52  ω     68.00  94.00   0.50    0.50    --   94.60  71.00 178.94   52
 53  ω     69.00 129.00   0.50    0.50    --   94.60  67.00   0.15  120
 54  ω     17.00  99.00   0.50    0.50    --   94.60 -61.00  60.00  164
 55  ω     69.00  94.00   0.50    0.50    --   94.60  67.00  83.01   50
 56  ω     72.00  98.00   0.50    0.50    --   94.60  61.00-180.00   52
 57  ω     67.00 124.00   0.50    0.50    --   94.60  71.00 122.76  114
 58  ω     45.00 126.00   0.50    0.50    --   94.60 -82.00-180.00  162
 59  ω      6.00 126.00   0.50    0.50    --   94.60 -82.00 -90.00  240
 60  ω     71.00  96.00   0.50    0.50    --   94.60  61.00 150.00   50
 61  ω    117.00 142.00   0.50    0.50    --   94.60  61.00 150.00   50
 62  ω     34.00 125.00   0.50    0.50    --   94.60 -82.00 -60.00  182
 63  ω    143.00 168.00   0.50    0.50    --   94.60  45.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2029525000
_diffrn_orient_matrix_UB_12      0.0411135000
_diffrn_orient_matrix_UB_13      -0.0606104000
_diffrn_orient_matrix_UB_21      0.0790340000
_diffrn_orient_matrix_UB_22      0.0295003000
_diffrn_orient_matrix_UB_23      -0.1300398000
_diffrn_orient_matrix_UB_31      -0.0720114000
_diffrn_orient_matrix_UB_32      -0.0835705000
_diffrn_orient_matrix_UB_33      -0.0757208000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                4086
_reflns_number_total             4094
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.166
_refine_ls_abs_structure_details 
;
 Flack x determined using 1916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4094
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.1515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0736
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C12(H12), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C9(H9A,H9B), C13(H13A,H13B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4161(2) 0.80929(10) 0.28837(16) 0.0162(3) Uani 1 1 d . . . . .
H1 H 0.3716 0.7522 0.2764 0.019 Uiso 1 1 calc R . . . .
C2 C 0.4944(2) 0.83945(10) 0.18281(16) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.5010(2) 0.78311(10) 0.05437(17) 0.0168(3) Uani 1 1 d . . . . .
C4 C 0.6220(2) 0.83557(11) -0.03453(17) 0.0203(3) Uani 1 1 d . . . . .
H4A H 0.7137 0.7985 -0.0740 0.024 Uiso 1 1 calc R . . . .
H4B H 0.5319 0.8645 -0.1130 0.024 Uiso 1 1 calc R . . . .
C5 C 0.7387(2) 0.90021(11) 0.06693(17) 0.0202(3) Uani 1 1 d . . . . .
H5A H 0.7684 0.9513 0.0154 0.024 Uiso 1 1 calc R . . . .
H5B H 0.8657 0.8755 0.1178 0.024 Uiso 1 1 calc R . . . .
C6 C 0.6023(2) 0.92295(10) 0.17100(16) 0.0155(3) Uani 1 1 d . . . . .
H6 H 0.6894 0.9351 0.2647 0.019 Uiso 1 1 calc R . . . .
C7 C 0.4702(2) 1.00253(10) 0.12577(16) 0.0165(3) Uani 1 1 d . . . . .
H7 H 0.5468 1.0390 0.0710 0.020 Uiso 1 1 calc R . . . .
C8 C 0.4469(2) 1.05506(9) 0.25499(16) 0.0157(3) Uani 1 1 d . . . . .
H8 H 0.5835 1.0686 0.3093 0.019 Uiso 1 1 calc R . . . .
C9 C 0.3314(2) 1.01324(10) 0.35648(16) 0.0164(3) Uani 1 1 d . . . . .
H9A H 0.2969 1.0569 0.4209 0.020 Uiso 1 1 calc R . . . .
H9B H 0.2054 0.9897 0.3018 0.020 Uiso 1 1 calc R . . . .
C10 C 0.4472(2) 0.94310(10) 0.44262(16) 0.0150(3) Uani 1 1 d . . . . .
C11 C 0.3857(2) 0.85021(10) 0.42386(16) 0.0163(3) Uani 1 1 d . . . . .
C12 C 0.5221(2) 0.80955(10) 0.55566(16) 0.0177(3) Uani 1 1 d . . . . .
H12 H 0.4496 0.8110 0.6354 0.021 Uiso 1 1 calc R . . . .
C13 C 0.7018(2) 0.86854(10) 0.59150(17) 0.0176(3) Uani 1 1 d . . . . .
H13A H 0.7564 0.8695 0.6941 0.021 Uiso 1 1 calc R . . . .
H13B H 0.8081 0.8515 0.5416 0.021 Uiso 1 1 calc R . . . .
C14 C 0.6141(2) 0.95328(10) 0.54007(16) 0.0155(3) Uani 1 1 d . . . . .
C15 C 0.7155(2) 1.03584(10) 0.59049(17) 0.0177(3) Uani 1 1 d . . . . .
H15 H 0.6344 1.0833 0.5398 0.021 Uiso 1 1 calc R . . . .
C16 C 0.2928(2) 0.76267(10) -0.02703(17) 0.0181(3) Uani 1 1 d . . . . .
H16A H 0.2240 0.7254 0.0300 0.022 Uiso 1 1 calc R . . . .
H16B H 0.2147 0.8156 -0.0476 0.022 Uiso 1 1 calc R . . . .
C17 C 0.2689(3) 0.98582(11) 0.02802(18) 0.0224(3) Uani 1 1 d . . . . .
H17A H 0.1950 0.9434 0.0708 0.034 Uiso 1 1 calc GR . . . .
H17B H 0.2905 0.9647 -0.0628 0.034 Uiso 1 1 calc GR . . . .
H17C H 0.1922 1.0386 0.0135 0.034 Uiso 1 1 calc GR . . . .
C18 C 0.1666(2) 0.83635(11) 0.43250(18) 0.0213(3) Uani 1 1 d . . . . .
H18A H 0.0804 0.8620 0.3502 0.032 Uiso 1 1 calc GR . . . .
H18B H 0.1406 0.8628 0.5185 0.032 Uiso 1 1 calc GR . . . .
H18C H 0.1393 0.7754 0.4343 0.032 Uiso 1 1 calc GR . . . .
C19 C 0.9243(3) 1.04004(12) 0.55638(19) 0.0233(3) Uani 1 1 d . . . . .
H19A H 1.0110 0.9985 0.6140 0.035 Uiso 1 1 calc GR . . . .
H19B H 0.9793 1.0971 0.5769 0.035 Uiso 1 1 calc GR . . . .
H19C H 0.9161 1.0272 0.4565 0.035 Uiso 1 1 calc GR . . . .
C20 C 0.7286(3) 1.04818(13) 0.74918(19) 0.0272(4) Uani 1 1 d . . . . .
H20A H 0.5948 1.0452 0.7702 0.041 Uiso 1 1 calc GR . . . .
H20B H 0.7873 1.1037 0.7776 0.041 Uiso 1 1 calc GR . . . .
H20C H 0.8121 1.0035 0.8010 0.041 Uiso 1 1 calc GR . . . .
C21 C 0.1170(3) 0.69673(14) -0.2326(2) 0.0308(4) Uani 1 1 d . . . . .
H21A H 0.0592 0.6541 -0.1791 0.046 Uiso 1 1 calc GR . . . .
H21B H 0.1314 0.6727 -0.3232 0.046 Uiso 1 1 calc GR . . . .
H21C H 0.0294 0.7464 -0.2489 0.046 Uiso 1 1 calc GR . . . .
C22 C 0.7772(3) 0.69789(13) 0.1759(2) 0.0296(4) Uani 1 1 d . . . . .
H22A H 0.8713 0.7252 0.1261 0.044 Uiso 1 1 calc GR . . . .
H22B H 0.8169 0.6388 0.1963 0.044 Uiso 1 1 calc GR . . . .
H22C H 0.7774 0.7280 0.2644 0.044 Uiso 1 1 calc GR . . . .
O1 O 0.34832(18) 1.13392(7) 0.21200(12) 0.0193(2) Uani 1 1 d . . . . .
H1A H 0.4122 1.1605 0.1604 0.029 Uiso 1 1 calc GR . . . .
O2 O 0.5681(2) 0.72386(8) 0.53110(13) 0.0263(3) Uani 1 1 d . . . . .
H2 H 0.6065 0.6991 0.6085 0.039 Uiso 1 1 calc GR . . . .
O3 O 0.30683(17) 0.72137(8) -0.15512(12) 0.0214(3) Uani 1 1 d . . . . .
O4 O 0.58297(18) 0.70033(7) 0.09043(12) 0.0217(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.335(2) . ?
C1 C11 1.515(2) . ?
C2 C3 1.538(2) . ?
C2 C6 1.526(2) . ?
C3 C4 1.550(2) . ?
C3 C16 1.520(2) . ?
C3 O4 1.4364(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.526(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.549(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.558(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.537(2) . ?
C7 C17 1.532(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.531(2) . ?
C8 O1 1.4367(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.512(2) . ?
C10 C11 1.525(2) . ?
C10 C14 1.339(2) . ?
C11 C12 1.561(2) . ?
C11 C18 1.537(2) . ?
C12 H12 1.0000 . ?
C12 C13 1.527(2) . ?
C12 O2 1.419(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.508(2) . ?
C14 C15 1.510(2) . ?
C15 H15 1.0000 . ?
C15 C19 1.534(2) . ?
C15 C20 1.535(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 O3 1.4224(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 O3 1.420(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 O4 1.420(2) . ?
O1 H1A 0.8400 . ?
O2 H2 0.8400 . ?

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
C2 C1 H1 114.4 . . ?
C2 C1 C11 131.25(14) . . ?
C11 C1 H1 114.4 . . ?
C1 C2 C3 119.77(14) . . ?
C1 C2 C6 129.85(14) . . ?
C6 C2 C3 110.14(13) . . ?
C2 C3 C4 104.36(13) . . ?
C16 C3 C2 111.46(12) . . ?
C16 C3 C4 112.09(13) . . ?
O4 C3 C2 113.69(13) . . ?
O4 C3 C4 113.15(13) . . ?
O4 C3 C16 102.37(13) . . ?
C3 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
C5 C4 C3 105.53(12) . . ?
C5 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C4 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
C4 C5 C6 105.52(13) . . ?
H5A C5 H5B 108.8 . . ?
C6 C5 H5A 110.6 . . ?
C6 C5 H5B 110.6 . . ?
C2 C6 C5 102.37(12) . . ?
C2 C6 H6 107.9 . . ?
C2 C6 C7 116.94(13) . . ?
C5 C6 H6 107.9 . . ?
C5 C6 C7 113.33(13) . . ?
C7 C6 H6 107.9 . . ?
C6 C7 H7 105.9 . . ?
C8 C7 C6 110.77(12) . . ?
C8 C7 H7 105.9 . . ?
C17 C7 C6 115.85(13) . . ?
C17 C7 H7 105.9 . . ?
C17 C7 C8 111.63(13) . . ?
C7 C8 H8 107.7 . . ?
C9 C8 C7 116.34(13) . . ?
C9 C8 H8 107.7 . . ?
O1 C8 C7 110.49(12) . . ?
O1 C8 H8 107.7 . . ?
O1 C8 C9 106.56(12) . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 C8 112.81(13) . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C9 C10 C11 122.35(14) . . ?
C14 C10 C9 125.56(15) . . ?
C14 C10 C11 112.08(14) . . ?
C1 C11 C10 115.44(13) . . ?
C1 C11 C12 111.74(13) . . ?
C1 C11 C18 107.04(13) . . ?
C10 C11 C12 101.02(12) . . ?
C10 C11 C18 112.33(13) . . ?
C18 C11 C12 109.15(13) . . ?
C11 C12 H12 108.3 . . ?
C13 C12 C11 105.01(13) . . ?
C13 C12 H12 108.3 . . ?
O2 C12 C11 111.76(13) . . ?
O2 C12 H12 108.3 . . ?
O2 C12 C13 114.99(14) . . ?
C12 C13 H13A 111.3 . . ?
C12 C13 H13B 111.3 . . ?
H13A C13 H13B 109.2 . . ?
C14 C13 C12 102.42(13) . . ?
C14 C13 H13A 111.3 . . ?
C14 C13 H13B 111.3 . . ?
C10 C14 C13 110.74(14) . . ?
C10 C14 C15 127.17(14) . . ?
C13 C14 C15 122.00(14) . . ?
C14 C15 H15 108.2 . . ?
C14 C15 C19 110.86(13) . . ?
C14 C15 C20 111.34(14) . . ?
C19 C15 H15 108.2 . . ?
C19 C15 C20 109.97(14) . . ?
C20 C15 H15 108.2 . . ?
C3 C16 H16A 109.8 . . ?
C3 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
O3 C16 C3 109.22(12) . . ?
O3 C16 H16A 109.8 . . ?
O3 C16 H16B 109.8 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
C8 O1 H1A 109.5 . . ?
C12 O2 H2 109.5 . . ?
C21 O3 C16 111.80(13) . . ?
C22 O4 C3 116.22(13) . . ?

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
O1 H1A O3 0.84 2.16 2.8843(17) 144.0 2_655
O1 H1A O4 0.84 2.52 3.2358(16) 144.0 2_655
O2 H2 O1 0.84 1.99 2.8227(17) 170.6 2_646

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 C4 -173.68(14) . . . . ?
C1 C2 C3 C16 65.14(19) . . . . ?
C1 C2 C3 O4 -49.94(19) . . . . ?
C1 C2 C6 C5 152.93(17) . . . . ?
C1 C2 C6 C7 -82.6(2) . . . . ?
C1 C11 C12 C13 97.41(14) . . . . ?
C1 C11 C12 O2 -27.89(18) . . . . ?
C2 C1 C11 C10 2.6(2) . . . . ?
C2 C1 C11 C12 -112.05(19) . . . . ?
C2 C1 C11 C18 128.50(18) . . . . ?
C2 C3 C4 C5 19.97(16) . . . . ?
C2 C3 C16 O3 171.50(13) . . . . ?
C2 C3 O4 C22 -56.13(18) . . . . ?
C2 C6 C7 C8 97.72(16) . . . . ?
C2 C6 C7 C17 -30.73(18) . . . . ?
C3 C2 C6 C5 -21.26(16) . . . . ?
C3 C2 C6 C7 103.23(14) . . . . ?
C3 C4 C5 C6 -33.87(17) . . . . ?
C3 C16 O3 C21 176.98(15) . . . . ?
C4 C3 C16 O3 54.94(18) . . . . ?
C4 C3 O4 C22 62.69(18) . . . . ?
C4 C5 C6 C2 33.55(16) . . . . ?
C4 C5 C6 C7 -93.30(15) . . . . ?
C5 C6 C7 C8 -143.54(13) . . . . ?
C5 C6 C7 C17 88.02(16) . . . . ?
C6 C2 C3 C4 1.19(16) . . . . ?
C6 C2 C3 C16 -120.00(14) . . . . ?
C6 C2 C3 O4 124.93(14) . . . . ?
C6 C7 C8 C9 -66.19(17) . . . . ?
C6 C7 C8 O1 172.17(12) . . . . ?
C7 C8 C9 C10 72.72(17) . . . . ?
C8 C9 C10 C11 -112.34(16) . . . . ?
C8 C9 C10 C14 66.2(2) . . . . ?
C9 C10 C11 C1 70.99(19) . . . . ?
C9 C10 C11 C12 -168.30(13) . . . . ?
C9 C10 C11 C18 -52.11(19) . . . . ?
C9 C10 C14 C13 -173.03(14) . . . . ?
C9 C10 C14 C15 3.6(3) . . . . ?
C10 C11 C12 C13 -25.88(15) . . . . ?
C10 C11 C12 O2 -151.18(13) . . . . ?
C10 C14 C15 C19 -117.15(18) . . . . ?
C10 C14 C15 C20 120.08(18) . . . . ?
C11 C1 C2 C3 -178.35(15) . . . . ?
C11 C1 C2 C6 7.9(3) . . . . ?
C11 C10 C14 C13 5.63(18) . . . . ?
C11 C10 C14 C15 -177.73(14) . . . . ?
C11 C12 C13 C14 29.21(15) . . . . ?
C12 C13 C14 C10 -22.21(17) . . . . ?
C12 C13 C14 C15 160.94(14) . . . . ?
C13 C14 C15 C19 59.15(19) . . . . ?
C13 C14 C15 C20 -63.62(19) . . . . ?
C14 C10 C11 C1 -107.71(16) . . . . ?
C14 C10 C11 C12 12.99(16) . . . . ?
C14 C10 C11 C18 129.18(15) . . . . ?
C16 C3 C4 C5 140.73(14) . . . . ?
C16 C3 O4 C22 -176.48(14) . . . . ?
C17 C7 C8 C9 64.51(17) . . . . ?
C17 C7 C8 O1 -57.13(16) . . . . ?
C18 C11 C12 C13 -144.40(13) . . . . ?
C18 C11 C12 O2 90.30(16) . . . . ?
O1 C8 C9 C10 -163.58(13) . . . . ?
O2 C12 C13 C14 152.46(13) . . . . ?
O4 C3 C4 C5 -104.12(15) . . . . ?
O4 C3 C16 O3 -66.62(15) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.551
_oxdiff_exptl_absorpt_empirical_full_min 0.741
####################################################################### 
# 
# 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_20180905_lfl_3-20-4
_database_code_depnum_ccdc_archive 'CCDC 1868707'
_audit_update_record             
;
2018-09-20 deposited with the CCDC.
2018-10-18 downloaded from the CCDC.
;
_audit_creation_date             2018-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H28 O2'
_chemical_formula_sum            'C19 H28 O2'
_chemical_formula_weight         288.41
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.08920(10)
_cell_length_b                   9.97190(10)
_cell_length_c                   17.83610(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1616.60(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24515
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6470
_cell_measurement_theta_min      4.9500
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.802
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            36958
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.898
_diffrn_reflns_theta_min         4.959
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  29.00   0.50    0.50    --    0.00 -77.00-150.00  116
  2  ω     32.00  67.00   0.50    0.50    --    0.00  38.00-120.00   70
  3  ω     44.00  85.00   0.50    0.50    --    0.00  57.00-180.00   82
  4  ω    -40.00  -8.00   0.50    0.50    --    0.00 -77.00 -60.00   64
  5  ω     -4.00  29.00   0.50    0.50    --    0.00  57.00-180.00   66
  6  ω     35.00  72.00   0.50    0.50    --    0.00  38.00-180.00   74
  7  ω     -9.00  16.00   0.50    0.50    --    0.00  38.00-120.00   50
  8  ω     46.00  74.00   0.50    0.50    --    0.00  38.00 120.00   56
  9  ω    -16.00   9.00   0.50    0.50    --    0.00  38.00-180.00   50
 10  ω    -17.00  61.00   0.50    0.50    --    0.00  19.00  60.00  156
 11  ω    -16.00  88.00   0.50    0.50    --    0.00  38.00 -60.00  208
 12  ω    -15.00  22.00   0.50    0.50    --    0.00  38.00 120.00   74
 13  ω     71.00  96.00   0.50    0.70    --   94.60  60.00  82.96   50
 14  ω     74.00 184.00   0.50    0.70    --   94.60  51.00  59.07  220
 15  ω     75.00 111.00   0.50    0.70    --   94.60  45.00 162.75   72
 16  ω     68.00  93.00   0.50    0.70    --   94.60  69.00 157.66   50
 17  ω    127.00 166.00   0.50    0.70    --   94.60  75.00 -38.55   78
 18  ω    159.00 184.00   0.50    0.70    --   94.60  67.00-132.73   50
 19  ω     69.00  97.00   0.50    0.70    --   94.60  66.00 165.01   56
 20  ω     68.00  93.00   0.50    0.70    --   94.60  69.00  27.18   50
 21  ω    146.00 172.00   0.50    0.70    --   94.60  73.00 174.60   52
 22  ω     66.00  94.00   0.50    0.70    --   94.60  75.00 -38.55   56
 23  ω    106.00 132.00   0.50    0.70    --   94.60  69.00  27.18   52
 24  ω     67.00  92.00   0.50    0.70    --   94.60  72.00  15.64   50
 25  ω     73.00 103.00   0.50    0.70    --   94.60  52.00   7.07   60
 26  ω     67.00  93.00   0.50    0.70    --   94.60  73.00 -11.26   52
 27  ω     66.00  91.00   0.50    0.70    --   94.60  75.00-161.57   50
 28  ω     75.00 133.00   0.50    0.70    --   94.60  47.00 -20.79  116
 29  ω     68.00 117.00   0.50    0.70    --   94.60  69.00-107.07   98
 30  ω     10.00  64.00   0.50    0.70    --   94.60 -82.00-150.00  108
 31  ω     67.00  94.00   0.50    0.70    --   94.60  73.00 174.60   54
 32  ω    107.00 184.00   0.50    0.70    --   94.60  67.00 101.07  154
 33  ω    111.00 146.00   0.50    0.70    --   94.60  67.00 119.81   70
 34  ω     69.00  94.00   0.50    0.70    --   94.60  67.00-132.73   50
 35  ω     71.00 135.00   0.50    0.70    --   94.60  61.00 -60.00  128
 36  ω      7.00 126.00   0.50    0.70    --   94.60 -82.00   0.00  238
 37  ω     70.00 103.00   0.50    0.70    --   94.60  67.00 101.07   66
 38  ω      6.00 121.00   0.50    0.70    --   94.60 -82.00-180.00  230
 39  ω     70.00  97.00   0.50    0.70    --   94.60  64.00  97.25   54
 40  ω     69.00  99.00   0.50    0.70    --   94.60  67.00 119.81   60
 41  ω     71.00  96.00   0.50    0.70    --   94.60  61.00 150.00   50
 42  ω    116.00 182.00   0.50    0.70    --   94.60  61.00 150.00  132
 43  ω     69.00 121.00   0.50    0.70    --   94.60  68.00-123.15  104
 44  ω     76.00 113.00   0.50    0.70    --   94.60  45.00  90.00   74
 45  ω      7.00  32.00   0.50    0.70    --   94.60 -77.00  30.00   50
 46  ω     40.00  77.00   0.50    0.70    --   94.60 -77.00  30.00   74
 47  ω     92.00 124.00   0.50    0.70    --   94.60 -77.00  30.00   64
 48  ω     71.00 105.00   0.50    0.70    --   94.60  61.00-150.00   68
 49  ω     71.00  97.00   0.50    0.70    --   94.60  61.00  90.00   52
 50  ω     67.00 110.00   0.50    0.70    --   94.60  71.00 -94.30   86
 51  ω    148.00 178.00   0.50    0.70    --   94.60  71.00 -94.30   60
 52  ω     72.00  98.00   0.50    0.70    --   94.60  61.00 -30.00   52
 53  ω     72.00 160.00   0.50    0.70    --   94.60  61.00-180.00  176
 54  ω     90.00 126.00   0.50    0.70    --   94.60 -82.00  90.00   72
 55  ω     74.00 184.00   0.50    0.70    --   94.60  50.00  28.20  220
 56  ω     71.00  97.00   0.50    0.70    --   94.60  61.00  60.00   52
 57  ω      5.00  83.00   0.50    0.70    --   94.60 -82.00  90.00  156
 58  ω     97.00 122.00   0.50    0.70    --   94.60 -82.00-150.00   50
 59  ω     13.00 126.00   0.50    0.70    --   94.60 -82.00 -90.00  226
 60  ω    152.00 177.00   0.50    0.70    --   94.60  60.00  82.96   50
 61  ω     72.00 177.00   0.50    0.70    --   94.60  55.00-131.77  210
 62  ω     67.00  93.00   0.50    0.70    --   94.60 -82.00-150.00   52
 63  ω    107.00 132.00   0.50    0.70    --   94.60  66.00 165.01   50
 64  ω    105.00 174.00   0.50    0.70    --   94.60  74.00 -88.09  138
 65  ω     66.00  91.00   0.50    0.70    --   94.60  74.00 -88.09   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0053726000
_diffrn_orient_matrix_UB_12      0.0618026000
_diffrn_orient_matrix_UB_13      0.0791352000
_diffrn_orient_matrix_UB_21      0.1568627000
_diffrn_orient_matrix_UB_22      0.0552552000
_diffrn_orient_matrix_UB_23      -0.0106617000
_diffrn_orient_matrix_UB_31      -0.0639147000
_diffrn_orient_matrix_UB_32      0.1304108000
_diffrn_orient_matrix_UB_33      -0.0329031000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3209
_reflns_number_total             3263
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1339 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+0.4420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,
 H13B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.73118(19) 0.19787(17) 0.34244(10) 0.0184(3) Uani 1 1 d . . . . .
H1A H 0.6307 0.2280 0.3291 0.022 Uiso 1 1 calc R . . . .
H1B H 0.7861 0.2775 0.3602 0.022 Uiso 1 1 calc R . . . .
C2 C 0.8048(2) 0.14678(17) 0.27246(9) 0.0184(4) Uani 1 1 d . . . . .
C3 C 0.9572(2) 0.17936(18) 0.25356(10) 0.0214(4) Uani 1 1 d . . . . .
C4 C 0.9968(2) 0.1094(2) 0.18087(11) 0.0276(4) Uani 1 1 d . . . . .
H4A H 1.0737 0.0407 0.1893 0.033 Uiso 1 1 calc R . . . .
H4B H 1.0330 0.1746 0.1433 0.033 Uiso 1 1 calc R . . . .
C5 C 0.8531(2) 0.04432(18) 0.15471(10) 0.0224(4) Uani 1 1 d . . . . .
H5A H 0.8182 0.0857 0.1075 0.027 Uiso 1 1 calc R . . . .
H5B H 0.8665 -0.0531 0.1466 0.027 Uiso 1 1 calc R . . . .
C6 C 0.7462(2) 0.07013(17) 0.21780(10) 0.0193(4) Uani 1 1 d . . . . .
C7 C 0.5939(2) 0.01275(18) 0.21951(10) 0.0197(4) Uani 1 1 d . . . . .
H7 H 0.5322 0.0741 0.2508 0.024 Uiso 1 1 calc R . . . .
C8 C 0.59137(19) -0.12733(17) 0.25792(10) 0.0183(3) Uani 1 1 d . . . . .
H8 H 0.4856 -0.1499 0.2667 0.022 Uiso 1 1 calc R . . . .
C9 C 0.66688(19) -0.13013(17) 0.33505(9) 0.0184(3) Uani 1 1 d . . . . .
H9A H 0.6474 -0.2182 0.3587 0.022 Uiso 1 1 calc R . . . .
H9B H 0.7745 -0.1228 0.3275 0.022 Uiso 1 1 calc R . . . .
C10 C 0.61911(19) -0.02109(17) 0.38863(9) 0.0179(4) Uani 1 1 d . . . . .
C11 C 0.71907(19) 0.09688(17) 0.40832(9) 0.0183(4) Uani 1 1 d . . . . .
C12 C 0.6336(2) 0.16466(18) 0.47318(10) 0.0214(4) Uani 1 1 d . . . . .
H12A H 0.6750 0.1374 0.5222 0.026 Uiso 1 1 calc R . . . .
H12B H 0.6395 0.2635 0.4689 0.026 Uiso 1 1 calc R . . . .
C13 C 0.4736(2) 0.11765(19) 0.46604(11) 0.0241(4) Uani 1 1 d . . . . .
H13A H 0.4298 0.1003 0.5159 0.029 Uiso 1 1 calc R . . . .
H13B H 0.4130 0.1850 0.4394 0.029 Uiso 1 1 calc R . . . .
C14 C 0.4861(2) -0.01047(18) 0.42098(10) 0.0206(4) Uani 1 1 d . . . . .
C15 C 0.3566(2) -0.10311(19) 0.41028(11) 0.0244(4) Uani 1 1 d . . . . .
H15 H 0.3928 -0.1852 0.3839 0.029 Uiso 1 1 calc R . . . .
C17 C 0.5213(2) 0.00425(19) 0.14218(10) 0.0250(4) Uani 1 1 d . . . . .
H17A H 0.5265 0.0920 0.1176 0.038 Uiso 1 1 calc GR . . . .
H17B H 0.4181 -0.0223 0.1479 0.038 Uiso 1 1 calc GR . . . .
H17C H 0.5729 -0.0624 0.1116 0.038 Uiso 1 1 calc GR . . . .
C18 C 0.8728(2) 0.05211(19) 0.43265(10) 0.0224(4) Uani 1 1 d . . . . .
H18A H 0.8644 -0.0128 0.4737 0.034 Uiso 1 1 calc GR . . . .
H18B H 0.9291 0.1302 0.4497 0.034 Uiso 1 1 calc GR . . . .
H18C H 0.9234 0.0103 0.3901 0.034 Uiso 1 1 calc GR . . . .
C19 C 0.2405(2) -0.0373(2) 0.36036(14) 0.0342(5) Uani 1 1 d . . . . .
H19A H 0.2028 0.0435 0.3850 0.051 Uiso 1 1 calc GR . . . .
H19B H 0.1595 -0.1003 0.3519 0.051 Uiso 1 1 calc GR . . . .
H19C H 0.2849 -0.0128 0.3122 0.051 Uiso 1 1 calc GR . . . .
C20 C 0.2892(3) -0.1474(3) 0.48496(13) 0.0444(6) Uani 1 1 d . . . . .
H20A H 0.3646 -0.1912 0.5156 0.067 Uiso 1 1 calc GR . . . .
H20B H 0.2086 -0.2105 0.4754 0.067 Uiso 1 1 calc GR . . . .
H20C H 0.2510 -0.0689 0.5116 0.067 Uiso 1 1 calc GR . . . .
O1 O 0.64925(14) -0.23041(13) 0.21130(7) 0.0220(3) Uani 1 1 d . . . . .
H1 H 0.7413 -0.2321 0.2153 0.033 Uiso 1 1 calc GR . . . .
O2 O 1.04037(15) 0.25106(14) 0.29040(7) 0.0269(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.505(2) . ?
C1 C11 1.551(2) . ?
C2 C3 1.462(2) . ?
C2 C6 1.349(2) . ?
C3 C4 1.516(3) . ?
C3 O2 1.230(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.531(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.509(2) . ?
C6 C7 1.498(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.556(2) . ?
C7 C17 1.531(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.538(2) . ?
C8 O1 1.423(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.511(2) . ?
C10 C11 1.527(2) . ?
C10 C14 1.343(2) . ?
C11 C12 1.549(2) . ?
C11 C18 1.530(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.533(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.514(2) . ?
C14 C15 1.509(2) . ?
C15 H15 1.0000 . ?
C15 C19 1.529(3) . ?
C15 C20 1.531(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1 H1 0.8400 . ?

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
H1A C1 H1B 107.4 . . ?
C2 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
C2 C1 C11 116.10(14) . . ?
C11 C1 H1A 108.3 . . ?
C11 C1 H1B 108.3 . . ?
C3 C2 C1 122.50(16) . . ?
C6 C2 C1 127.98(16) . . ?
C6 C2 C3 109.50(16) . . ?
C2 C3 C4 108.65(15) . . ?
O2 C3 C2 126.00(17) . . ?
O2 C3 C4 125.35(17) . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
C3 C4 C5 104.67(15) . . ?
H4A C4 H4B 108.9 . . ?
C5 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C4 C5 H5A 110.9 . . ?
C4 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C6 C5 C4 104.47(15) . . ?
C6 C5 H5A 110.9 . . ?
C6 C5 H5B 110.9 . . ?
C2 C6 C5 112.40(16) . . ?
C2 C6 C7 124.54(16) . . ?
C7 C6 C5 123.04(16) . . ?
C6 C7 H7 107.2 . . ?
C6 C7 C8 111.43(15) . . ?
C6 C7 C17 113.62(15) . . ?
C8 C7 H7 107.2 . . ?
C17 C7 H7 107.2 . . ?
C17 C7 C8 109.91(14) . . ?
C7 C8 H8 106.5 . . ?
C9 C8 C7 113.80(14) . . ?
C9 C8 H8 106.5 . . ?
O1 C8 C7 112.70(14) . . ?
O1 C8 H8 106.5 . . ?
O1 C8 C9 110.16(14) . . ?
C8 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 C8 115.12(14) . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C9 C10 C11 121.91(15) . . ?
C14 C10 C9 125.93(16) . . ?
C14 C10 C11 112.07(15) . . ?
C10 C11 C1 111.59(13) . . ?
C10 C11 C12 102.09(14) . . ?
C10 C11 C18 112.57(14) . . ?
C12 C11 C1 108.55(14) . . ?
C18 C11 C1 109.85(14) . . ?
C18 C11 C12 111.94(14) . . ?
C11 C12 H12A 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C13 C12 C11 106.28(14) . . ?
C13 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
C12 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
C14 C13 C12 103.34(14) . . ?
C14 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
C10 C14 C13 111.24(16) . . ?
C10 C14 C15 126.83(16) . . ?
C15 C14 C13 121.69(16) . . ?
C14 C15 H15 107.7 . . ?
C14 C15 C19 110.45(16) . . ?
C14 C15 C20 112.27(17) . . ?
C19 C15 H15 107.7 . . ?
C19 C15 C20 110.74(18) . . ?
C20 C15 H15 107.7 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 O1 H1 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 C4 178.72(16) . . . . ?
C1 C2 C3 O2 -1.0(3) . . . . ?
C1 C2 C6 C5 177.49(16) . . . . ?
C1 C2 C6 C7 -4.2(3) . . . . ?
C1 C11 C12 C13 97.18(16) . . . . ?
C2 C1 C11 C10 -65.32(19) . . . . ?
C2 C1 C11 C12 -177.06(15) . . . . ?
C2 C1 C11 C18 60.25(19) . . . . ?
C2 C3 C4 C5 5.1(2) . . . . ?
C2 C6 C7 C8 -89.2(2) . . . . ?
C2 C6 C7 C17 145.99(17) . . . . ?
C3 C2 C6 C5 -1.0(2) . . . . ?
C3 C2 C6 C7 177.32(16) . . . . ?
C3 C4 C5 C6 -5.38(19) . . . . ?
C4 C5 C6 C2 4.2(2) . . . . ?
C4 C5 C6 C7 -174.18(17) . . . . ?
C5 C6 C7 C8 88.93(19) . . . . ?
C5 C6 C7 C17 -35.9(2) . . . . ?
C6 C2 C3 C4 -2.7(2) . . . . ?
C6 C2 C3 O2 177.58(18) . . . . ?
C6 C7 C8 C9 51.11(19) . . . . ?
C6 C7 C8 O1 -75.25(18) . . . . ?
C7 C8 C9 C10 49.8(2) . . . . ?
C8 C9 C10 C11 -107.64(18) . . . . ?
C8 C9 C10 C14 68.6(2) . . . . ?
C9 C10 C11 C1 73.30(19) . . . . ?
C9 C10 C11 C12 -170.94(15) . . . . ?
C9 C10 C11 C18 -50.8(2) . . . . ?
C9 C10 C14 C13 -175.14(16) . . . . ?
C9 C10 C14 C15 -0.7(3) . . . . ?
C10 C11 C12 C13 -20.78(17) . . . . ?
C10 C14 C15 C19 -105.1(2) . . . . ?
C10 C14 C15 C20 130.8(2) . . . . ?
C11 C1 C2 C3 -101.40(19) . . . . ?
C11 C1 C2 C6 80.3(2) . . . . ?
C11 C10 C14 C13 1.4(2) . . . . ?
C11 C10 C14 C15 175.78(17) . . . . ?
C11 C12 C13 C14 21.77(18) . . . . ?
C12 C13 C14 C10 -14.7(2) . . . . ?
C12 C13 C14 C15 170.55(16) . . . . ?
C13 C14 C15 C19 68.8(2) . . . . ?
C13 C14 C15 C20 -55.4(2) . . . . ?
C14 C10 C11 C1 -103.40(17) . . . . ?
C14 C10 C11 C12 12.36(18) . . . . ?
C14 C10 C11 C18 132.55(16) . . . . ?
C17 C7 C8 C9 177.98(15) . . . . ?
C17 C7 C8 O1 51.61(19) . . . . ?
C18 C11 C12 C13 -141.41(15) . . . . ?
O1 C8 C9 C10 177.49(14) . . . . ?
O2 C3 C4 C5 -175.19(18) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.179
_oxdiff_exptl_absorpt_empirical_full_min 0.528
