# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_160107_shy20160105
_database_code_depnum_ccdc_archive 'CCDC 1857510'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_audit_creation_date             2016-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            '(R)-6, 6?-HMSIOL'
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H28 O2, C6 H14 O'
_chemical_formula_sum            'C29 H42 O3'
_chemical_formula_weight         438.63
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h19 n2 o8'
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 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   10.8110(4)
_cell_length_b                   11.3987(3)
_cell_length_c                   11.7982(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.616(4)
_cell_angle_gamma                90.00
_cell_volume                     1406.84(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4305
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.2475
_cell_measurement_theta_min      3.8688
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.035
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10334
_diffrn_reflns_theta_full        67.36
_diffrn_reflns_theta_max         67.36
_diffrn_reflns_theta_min         3.87
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1094580000
_diffrn_orient_matrix_UB_12      0.0547831000
_diffrn_orient_matrix_UB_13      0.0947911000
_diffrn_orient_matrix_UB_21      -0.0767755000
_diffrn_orient_matrix_UB_22      -0.0200570000
_diffrn_orient_matrix_UB_23      0.0919467000
_diffrn_orient_matrix_UB_31      0.0617643000
_diffrn_orient_matrix_UB_32      -0.1219777000
_diffrn_orient_matrix_UB_33      0.0273761000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4155
_reflns_number_total             4921
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack (1983), 2281 Friedel pairs'
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       0.0109(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4921
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0777P)²+0.0922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1356
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H1-O1
 0.86 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C25(H25), C27(H27)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C17(H17), C20(H20)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,
 H26B,H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O -0.04726(16) 1.06850(16) 0.10650(14) 0.0694(5) Uani 1 d . . D
H1 H 0.025(2) 1.078(3) 0.088(3) 0.095(10) Uiso 1 d . . D
O2 O 0.2564(2) 0.5320(2) 0.09114(16) 0.0918(6) Uani 1 d . . .
H2 H 0.1809 0.5446 0.0597 0.138 Uiso 1 calc . . GR
C1 C 0.0672(2) 0.93433(18) 0.25276(18) 0.0513(5) Uani 1 d . . .
H1A H 0.1400 0.9426 0.2251 0.062 Uiso 1 calc . . R
C2 C -0.04238(19) 0.99662(18) 0.20155(17) 0.0526(5) Uani 1 d . . .
C3 C -0.1523(2) 0.9884(2) 0.24348(18) 0.0556(5) Uani 1 d . . .
C4 C -0.1484(2) 0.9127(2) 0.33654(19) 0.0578(5) Uani 1 d . . .
H4 H -0.2202 0.9060 0.3660 0.069 Uiso 1 calc . . R
C5 C -0.0409(2) 0.84700(19) 0.38673(17) 0.0523(5) Uani 1 d . . .
C6 C 0.06798(18) 0.85973(18) 0.34536(16) 0.0489(4) Uani 1 d . . .
C7 C 0.1786(2) 0.7869(2) 0.41418(18) 0.0547(5) Uani 1 d . . .
C8 C 0.1082(3) 0.7018(2) 0.4803(2) 0.0709(7) Uani 1 d . . .
H8A H 0.0909 0.6279 0.4386 0.085 Uiso 1 calc . . R
H8B H 0.1612 0.6863 0.5584 0.085 Uiso 1 calc . . R
C9 C -0.0191(2) 0.7602(2) 0.4881(2) 0.0648(6) Uani 1 d . . .
C10 C -0.2696(2) 1.0591(3) 0.1896(2) 0.0778(7) Uani 1 d . . .
H10A H -0.3016 1.0369 0.1090 0.117 Uiso 1 calc . . GR
H10B H -0.2483 1.1410 0.1942 0.117 Uiso 1 calc . . GR
H10C H -0.3338 1.0446 0.2312 0.117 Uiso 1 calc . . GR
C11 C -0.1254(3) 0.6694(3) 0.4733(3) 0.0964(9) Uani 1 d . . .
H11A H -0.2035 0.7076 0.4766 0.145 Uiso 1 calc . . GR
H11B H -0.1029 0.6124 0.5350 0.145 Uiso 1 calc . . GR
H11C H -0.1367 0.6310 0.3990 0.145 Uiso 1 calc . . GR
C12 C -0.0051(3) 0.8247(3) 0.6046(2) 0.0898(9) Uani 1 d . . .
H12A H 0.0658 0.8779 0.6169 0.135 Uiso 1 calc . . GR
H12B H 0.0095 0.7687 0.6674 0.135 Uiso 1 calc . . GR
H12C H -0.0820 0.8678 0.6024 0.135 Uiso 1 calc . . GR
C13 C 0.2847(2) 0.8636(3) 0.4938(2) 0.0727(7) Uani 1 d . . .
H13A H 0.2779 0.9437 0.4652 0.087 Uiso 1 calc . . R
H13B H 0.2744 0.8641 0.5731 0.087 Uiso 1 calc . . R
C14 C 0.4148(2) 0.8138(2) 0.4933(2) 0.0746(7) Uani 1 d . . .
C15 C 0.3846(2) 0.73789(19) 0.38518(19) 0.0572(5) Uani 1 d . . .
C16 C 0.25433(19) 0.72288(17) 0.34117(17) 0.0501(5) Uani 1 d . . .
C17 C 0.2086(2) 0.65523(19) 0.24228(18) 0.0579(5) Uani 1 d . . .
H17 H 0.1210 0.6459 0.2117 0.069 Uiso 1 calc . . R
C18 C 0.2945(2) 0.6013(2) 0.18896(19) 0.0619(6) Uani 1 d . . .
C19 C 0.4256(2) 0.6143(2) 0.2330(2) 0.0670(6) Uani 1 d . . .
C20 C 0.4685(2) 0.6839(2) 0.3310(2) 0.0672(6) Uani 1 d . . .
H20 H 0.5559 0.6946 0.3610 0.081 Uiso 1 calc . . R
C21 C 0.5176(4) 0.9035(4) 0.4944(5) 0.1449(18) Uani 1 d . . .
H21A H 0.5927 0.8648 0.4837 0.217 Uiso 1 calc . . GR
H21B H 0.5378 0.9440 0.5681 0.217 Uiso 1 calc . . GR
H21C H 0.4877 0.9587 0.4321 0.217 Uiso 1 calc . . GR
C22 C 0.4635(4) 0.7337(4) 0.6039(3) 0.1262(16) Uani 1 d . . .
H22A H 0.3976 0.6791 0.6093 0.189 Uiso 1 calc . . GR
H22B H 0.4845 0.7816 0.6730 0.189 Uiso 1 calc . . GR
H22C H 0.5380 0.6914 0.5970 0.189 Uiso 1 calc . . GR
C23 C 0.5168(3) 0.5543(4) 0.1735(3) 0.1045(11) Uani 1 d . . .
H23A H 0.5051 0.5853 0.0959 0.157 Uiso 1 calc . . GR
H23B H 0.5000 0.4715 0.1692 0.157 Uiso 1 calc . . GR
H23C H 0.6031 0.5680 0.2177 0.157 Uiso 1 calc . . GR
O3 O 0.18378(16) 1.06161(17) 0.04646(15) 0.0747(5) Uani 1 d . . .
C24 C 0.2271(5) 1.2307(4) 0.1680(4) 0.1291(15) Uani 1 d . . .
H24A H 0.1374 1.2474 0.1533 0.194 Uiso 1 calc . . GR
H24B H 0.2746 1.3027 0.1827 0.194 Uiso 1 calc . . GR
H24C H 0.2526 1.1803 0.2350 0.194 Uiso 1 calc . . GR
C25 C 0.2538(3) 1.1696(3) 0.0606(4) 0.0996(11) Uani 1 d . . .
H25 H 0.3454 1.1530 0.0752 0.120 Uiso 1 calc . . R
C26 C 0.2114(6) 1.2451(4) -0.0481(4) 0.1437(18) Uani 1 d . . .
H26A H 0.2173 1.2006 -0.1156 0.216 Uiso 1 calc . . GR
H26B H 0.2656 1.3129 -0.0408 0.216 Uiso 1 calc . . GR
H26C H 0.1246 1.2696 -0.0567 0.216 Uiso 1 calc . . GR
C27 C 0.2267(3) 0.9703(3) -0.0177(3) 0.0959(10) Uani 1 d . . .
H27 H 0.2508 1.0041 -0.0854 0.115 Uiso 1 calc . . R
C28 C 0.3391(5) 0.9062(4) 0.0577(5) 0.1344(16) Uani 1 d . . .
H28A H 0.4076 0.9605 0.0867 0.202 Uiso 1 calc . . GR
H28B H 0.3669 0.8466 0.0122 0.202 Uiso 1 calc . . GR
H28C H 0.3146 0.8705 0.1225 0.202 Uiso 1 calc . . GR
C29 C 0.1145(5) 0.8889(4) -0.0596(4) 0.1415(17) Uani 1 d . . .
H29A H 0.0919 0.8545 0.0068 0.212 Uiso 1 calc . . GR
H29B H 0.1371 0.8280 -0.1068 0.212 Uiso 1 calc . . GR
H29C H 0.0431 0.9323 -0.1052 0.212 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.872(18) . ?
O1 C2 1.379(3) . ?
O2 H2 0.8200 . ?
O2 C18 1.373(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.382(3) . ?
C1 C6 1.383(3) . ?
C2 C3 1.401(3) . ?
C3 C4 1.388(3) . ?
C3 C10 1.501(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 C6 1.391(3) . ?
C5 C9 1.524(3) . ?
C6 C7 1.513(3) . ?
C7 C8 1.559(3) . ?
C7 C13 1.555(3) . ?
C7 C16 1.517(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.552(4) . ?
C9 C11 1.523(4) . ?
C9 C12 1.532(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.518(4) . ?
C14 C15 1.507(3) . ?
C14 C21 1.507(5) . ?
C14 C22 1.571(5) . ?
C15 C16 1.383(3) . ?
C15 C20 1.379(3) . ?
C16 C17 1.382(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(3) . ?
C18 C19 1.389(3) . ?
C19 C20 1.382(3) . ?
C19 C23 1.510(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O3 C25 1.433(4) . ?
O3 C27 1.432(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24 C25 1.535(6) . ?
C25 H25 0.9800 . ?
C25 C26 1.515(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27 0.9800 . ?
C27 C28 1.502(6) . ?
C27 C29 1.508(6) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 115(2) . . ?
C18 O2 H2 109.5 . . ?
C2 C1 H1A 120.2 . . ?
C2 C1 C6 119.66(18) . . ?
C6 C1 H1A 120.2 . . ?
O1 C2 C1 120.88(17) . . ?
O1 C2 C3 117.72(18) . . ?
C1 C2 C3 121.40(18) . . ?
C2 C3 C10 121.0(2) . . ?
C4 C3 C2 117.50(19) . . ?
C4 C3 C10 121.5(2) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 121.94(19) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 119.16(19) . . ?
C4 C5 C9 129.34(18) . . ?
C6 C5 C9 111.48(18) . . ?
C1 C6 C5 120.29(18) . . ?
C1 C6 C7 127.43(18) . . ?
C5 C6 C7 112.27(17) . . ?
C6 C7 C8 100.96(17) . . ?
C6 C7 C13 112.25(19) . . ?
C6 C7 C16 115.22(17) . . ?
C13 C7 C8 115.2(2) . . ?
C16 C7 C8 112.76(19) . . ?
C16 C7 C13 101.07(17) . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 C7 108.38(18) . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
C5 C9 C8 101.29(17) . . ?
C5 C9 C12 110.7(2) . . ?
C11 C9 C5 112.8(2) . . ?
C11 C9 C8 110.9(2) . . ?
C11 C9 C12 109.3(2) . . ?
C12 C9 C8 111.7(2) . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.8 . . ?
C7 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C14 C13 C7 109.3(2) . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
C13 C14 C22 109.3(3) . . ?
C15 C14 C13 102.41(18) . . ?
C15 C14 C21 113.5(3) . . ?
C15 C14 C22 109.0(2) . . ?
C21 C14 C13 115.3(3) . . ?
C21 C14 C22 107.2(3) . . ?
C16 C15 C14 111.82(19) . . ?
C20 C15 C14 128.4(2) . . ?
C20 C15 C16 119.8(2) . . ?
C15 C16 C7 111.80(18) . . ?
C17 C16 C7 128.21(19) . . ?
C17 C16 C15 119.99(19) . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
O2 C18 C17 122.8(2) . . ?
O2 C18 C19 115.9(2) . . ?
C19 C18 C17 121.3(2) . . ?
C18 C19 C23 120.1(2) . . ?
C20 C19 C18 118.0(2) . . ?
C20 C19 C23 121.9(2) . . ?
C15 C20 C19 121.5(2) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C27 O3 C25 117.0(2) . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
O3 C25 C24 106.4(3) . . ?
O3 C25 H25 109.6 . . ?
O3 C25 C26 110.6(3) . . ?
C24 C25 H25 109.6 . . ?
C26 C25 C24 111.2(3) . . ?
C26 C25 H25 109.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O3 C27 H27 109.4 . . ?
O3 C27 C28 111.2(3) . . ?
O3 C27 C29 106.2(3) . . ?
C28 C27 H27 109.4 . . ?
C28 C27 C29 111.0(4) . . ?
C29 C27 H27 109.4 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 177.76(19) . . . . ?
O1 C2 C3 C10 -2.3(3) . . . . ?
O2 C18 C19 C20 179.6(2) . . . . ?
O2 C18 C19 C23 0.2(4) . . . . ?
C1 C2 C3 C4 -1.7(3) . . . . ?
C1 C2 C3 C10 178.2(2) . . . . ?
C1 C6 C7 C8 -166.0(2) . . . . ?
C1 C6 C7 C13 70.8(3) . . . . ?
C1 C6 C7 C16 -44.2(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C1 C6 C7 -178.43(19) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 2.1(3) . . . . ?
C3 C4 C5 C9 -179.9(2) . . . . ?
C4 C5 C6 C1 -2.1(3) . . . . ?
C4 C5 C6 C7 176.7(2) . . . . ?
C4 C5 C9 C8 168.9(2) . . . . ?
C4 C5 C9 C11 50.3(4) . . . . ?
C4 C5 C9 C12 -72.5(3) . . . . ?
C5 C6 C7 C8 15.3(2) . . . . ?
C5 C6 C7 C13 -107.9(2) . . . . ?
C5 C6 C7 C16 137.10(19) . . . . ?
C6 C1 C2 O1 -177.73(19) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
C6 C5 C9 C8 -13.0(3) . . . . ?
C6 C5 C9 C11 -131.6(2) . . . . ?
C6 C5 C9 C12 105.6(2) . . . . ?
C6 C7 C8 C9 -23.2(2) . . . . ?
C6 C7 C13 C14 -141.7(2) . . . . ?
C6 C7 C16 C15 132.5(2) . . . . ?
C6 C7 C16 C17 -47.9(3) . . . . ?
C7 C8 C9 C5 22.4(3) . . . . ?
C7 C8 C9 C11 142.4(2) . . . . ?
C7 C8 C9 C12 -95.5(2) . . . . ?
C7 C13 C14 C15 18.5(3) . . . . ?
C7 C13 C14 C21 142.3(3) . . . . ?
C7 C13 C14 C22 -96.9(3) . . . . ?
C7 C16 C17 C18 -178.6(2) . . . . ?
C8 C7 C13 C14 103.5(3) . . . . ?
C8 C7 C16 C15 -112.3(2) . . . . ?
C8 C7 C16 C17 67.3(3) . . . . ?
C9 C5 C6 C1 179.59(19) . . . . ?
C9 C5 C6 C7 -1.6(3) . . . . ?
C10 C3 C4 C5 179.9(2) . . . . ?
C13 C7 C8 C9 98.0(2) . . . . ?
C13 C7 C16 C15 11.3(2) . . . . ?
C13 C7 C16 C17 -169.1(2) . . . . ?
C13 C14 C15 C16 -11.5(3) . . . . ?
C13 C14 C15 C20 169.8(2) . . . . ?
C14 C15 C16 C7 -0.1(3) . . . . ?
C14 C15 C16 C17 -179.7(2) . . . . ?
C14 C15 C20 C19 178.5(2) . . . . ?
C15 C16 C17 C18 1.0(3) . . . . ?
C16 C7 C8 C9 -146.7(2) . . . . ?
C16 C7 C13 C14 -18.4(3) . . . . ?
C16 C15 C20 C19 -0.2(3) . . . . ?
C16 C17 C18 O2 179.4(2) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 -0.8(4) . . . . ?
C17 C18 C19 C23 179.8(3) . . . . ?
C18 C19 C20 C15 1.0(4) . . . . ?
C20 C15 C16 C7 178.8(2) . . . . ?
C20 C15 C16 C17 -0.8(3) . . . . ?
C21 C14 C15 C16 -136.5(3) . . . . ?
C21 C14 C15 C20 44.7(4) . . . . ?
C22 C14 C15 C16 104.2(3) . . . . ?
C22 C14 C15 C20 -74.6(4) . . . . ?
C23 C19 C20 C15 -179.6(3) . . . . ?
C25 O3 C27 C28 80.3(3) . . . . ?
C25 O3 C27 C29 -158.8(3) . . . . ?
C27 O3 C25 C24 -157.8(3) . . . . ?
C27 O3 C25 C26 81.4(4) . . . . ?

