# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_20151014zy_gk_0m
_audit_block_doi                 10.5517/cc1k3w3n
_database_code_depnum_ccdc_archive 'CCDC 1433691'
_audit_update_record             
;
2015-10-28 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'diethyl 7,9-di-tert-butyl-4-(4-chlorophenyl)-8-oxospiro[4.5]deca-2,6,9-triene-1,1-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H36 Cl N0 O5'
_chemical_formula_weight         512.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   9.7421(6)
_cell_length_b                   16.0093(9)
_cell_length_c                   19.0370(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.910(2)
_cell_angle_gamma                90.00
_cell_volume                     2958.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6590
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      25.63

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1092
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_T_max  0.9650
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20847
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5212
_reflns_number_gt                3468
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0856P)²+1.3051P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.053(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5212
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1870
_refine_ls_wR_factor_gt          0.1640
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3332(5) 0.5774(2) 0.4360(3) 0.1169(15) Uani 1 1 d . . .
H1A H 0.2762 0.5656 0.3935 0.175 Uiso 1 1 calc R . .
H1B H 0.2768 0.5973 0.4714 0.175 Uiso 1 1 calc R . .
H1C H 0.3801 0.5274 0.4524 0.175 Uiso 1 1 calc R . .
C2 C 0.5322(4) 0.6099(2) 0.3683(2) 0.1093(14) Uani 1 1 d . . .
H2A H 0.5782 0.5607 0.3872 0.164 Uiso 1 1 calc R . .
H2B H 0.5993 0.6514 0.3590 0.164 Uiso 1 1 calc R . .
H2C H 0.4784 0.5960 0.3253 0.164 Uiso 1 1 calc R . .
C3 C 0.4384(3) 0.64376(17) 0.42121(15) 0.0680(8) Uani 1 1 d . . .
C4 C 0.5280(5) 0.6617(2) 0.4894(2) 0.1086(15) Uani 1 1 d . . .
H4A H 0.5788 0.6124 0.5039 0.163 Uiso 1 1 calc R . .
H4B H 0.4704 0.6778 0.5256 0.163 Uiso 1 1 calc R . .
H4C H 0.5910 0.7061 0.4816 0.163 Uiso 1 1 calc R . .
C5 C 0.3661(3) 0.72300(14) 0.39314(12) 0.0482(6) Uani 1 1 d . . .
C6 C 0.3757(3) 0.79444(15) 0.42794(12) 0.0483(6) Uani 1 1 d . . .
H6 H 0.4304 0.7951 0.4704 0.058 Uiso 1 1 calc R . .
C7 C 0.3068(2) 0.87363(14) 0.40512(12) 0.0466(6) Uani 1 1 d . . .
C8 C 0.2299(2) 0.86636(14) 0.33404(12) 0.0453(6) Uani 1 1 d . . .
H8 H 0.1876 0.9144 0.3152 0.054 Uiso 1 1 calc R . .
C9 C 0.2168(2) 0.79785(15) 0.29559(12) 0.0470(6) Uani 1 1 d . . .
C10 C 0.2789(3) 0.71893(15) 0.32528(14) 0.0570(7) Uani 1 1 d . . .
C11 C 0.1407(3) 0.79639(17) 0.22151(14) 0.0621(8) Uani 1 1 d . . .
C12 C 0.0894(4) 0.8839(2) 0.19995(17) 0.0880(11) Uani 1 1 d . . .
H12A H 0.0279 0.9037 0.2331 0.132 Uiso 1 1 calc R . .
H12B H 0.0415 0.8817 0.1538 0.132 Uiso 1 1 calc R . .
H12C H 0.1665 0.9212 0.1995 0.132 Uiso 1 1 calc R . .
C13 C 0.2401(4) 0.7664(3) 0.16851(17) 0.1081(14) Uani 1 1 d . . .
H13A H 0.3173 0.8037 0.1693 0.162 Uiso 1 1 calc R . .
H13B H 0.1932 0.7656 0.1220 0.162 Uiso 1 1 calc R . .
H13C H 0.2718 0.7112 0.1810 0.162 Uiso 1 1 calc R . .
C14 C 0.0159(4) 0.7392(2) 0.2196(2) 0.0942(12) Uani 1 1 d . . .
H14A H 0.0456 0.6831 0.2301 0.141 Uiso 1 1 calc R . .
H14B H -0.0324 0.7410 0.1735 0.141 Uiso 1 1 calc R . .
H14C H -0.0442 0.7575 0.2539 0.141 Uiso 1 1 calc R . .
C15 C 0.4127(3) 0.94889(15) 0.40285(14) 0.0532(7) Uani 1 1 d . . .
H15 H 0.4818 0.9430 0.4430 0.064 Uiso 1 1 calc R . .
C16 C 0.3232(3) 1.02241(17) 0.41668(15) 0.0644(8) Uani 1 1 d . . .
H16 H 0.3467 1.0772 0.4069 0.077 Uiso 1 1 calc R . .
C17 C 0.2091(3) 1.00187(17) 0.44372(15) 0.0644(8) Uani 1 1 d . . .
H17 H 0.1409 1.0397 0.4537 0.077 Uiso 1 1 calc R . .
C18 C 0.2017(3) 0.90840(16) 0.45676(13) 0.0536(7) Uani 1 1 d . . .
C19 C 0.2485(3) 0.89658(17) 0.53523(14) 0.0619(7) Uani 1 1 d . . .
C20 C 0.1680(5) 0.8985(3) 0.64966(19) 0.1078(13) Uani 1 1 d . . .
H20A H 0.2654 0.9063 0.6632 0.129 Uiso 1 1 calc R . .
H20B H 0.1172 0.9424 0.6712 0.129 Uiso 1 1 calc R . .
C21 C 0.1256(9) 0.8210(6) 0.6716(3) 0.230(4) Uani 1 1 d . . .
H21A H 0.0884 0.7825 0.6386 0.276 Uiso 1 1 calc R . .
H21B H 0.1344 0.8073 0.7192 0.276 Uiso 1 1 calc R . .
C22 C 0.4860(3) 0.94941(15) 0.33696(14) 0.0525(7) Uani 1 1 d . . .
C23 C 0.6026(3) 0.9018(2) 0.33264(17) 0.0726(9) Uani 1 1 d . . .
H23 H 0.6390 0.8729 0.3724 0.087 Uiso 1 1 calc R . .
C24 C 0.6669(3) 0.8957(2) 0.2713(2) 0.0856(10) Uani 1 1 d . . .
H24 H 0.7444 0.8621 0.2693 0.103 Uiso 1 1 calc R . .
C25 C 0.6156(4) 0.9394(2) 0.21335(18) 0.0771(9) Uani 1 1 d . . .
C26 C 0.5022(3) 0.9895(2) 0.21642(18) 0.0756(9) Uani 1 1 d . . .
H26 H 0.4683 1.0200 0.1771 0.091 Uiso 1 1 calc R . .
C27 C 0.4394(3) 0.99439(17) 0.27790(16) 0.0658(8) Uani 1 1 d . . .
H27 H 0.3632 1.0290 0.2799 0.079 Uiso 1 1 calc R . .
C28 C 0.0595(3) 0.87091(19) 0.44052(15) 0.0627(7) Uani 1 1 d . . .
C29 C -0.0694(4) 0.7458(3) 0.4453(3) 0.1171(14) Uani 1 1 d . . .
H29A H -0.1358 0.7704 0.4744 0.141 Uiso 1 1 calc R . .
H29B H -0.1052 0.7511 0.3964 0.141 Uiso 1 1 calc R . .
C30 C -0.0515(6) 0.6616(4) 0.4623(6) 0.221(4) Uani 1 1 d . . .
H30A H 0.0212 0.6389 0.4371 0.331 Uiso 1 1 calc R . .
H30B H -0.1354 0.6319 0.4495 0.331 Uiso 1 1 calc R . .
H30C H -0.0278 0.6561 0.5121 0.331 Uiso 1 1 calc R . .
Cl1 Cl 0.69432(13) 0.93106(9) 0.13481(6) 0.1241(5) Uani 1 1 d . . .
O1 O 0.1414(2) 0.90160(15) 0.57253(11) 0.0824(7) Uani 1 1 d . . .
O2 O 0.3649(2) 0.88883(16) 0.55938(11) 0.0862(7) Uani 1 1 d . . .
O3 O -0.0400(2) 0.90749(15) 0.41569(13) 0.0894(7) Uani 1 1 d . . .
O4 O 0.0611(2) 0.79025(13) 0.45647(12) 0.0756(6) Uani 1 1 d . . .
O5 O 0.2590(3) 0.65290(13) 0.29470(13) 0.1090(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.519(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.517(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C5 1.525(3) . ?
C3 C4 1.529(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.321(3) . ?
C5 C10 1.485(3) . ?
C6 C7 1.482(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.494(3) . ?
C7 C18 1.580(4) . ?
C7 C15 1.589(3) . ?
C8 C9 1.319(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.491(3) . ?
C9 C11 1.536(3) . ?
C10 O5 1.214(3) . ?
C11 C14 1.519(4) . ?
C11 C12 1.532(4) . ?
C11 C13 1.534(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C22 1.496(4) . ?
C15 C16 1.501(4) . ?
C15 H15 0.9800 . ?
C16 C17 1.307(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.520(4) . ?
C17 H17 0.9300 . ?
C18 C28 1.517(4) . ?
C18 C19 1.536(4) . ?
C19 O2 1.193(3) . ?
C19 O1 1.314(4) . ?
C20 C21 1.384(8) . ?
C20 O1 1.470(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9300 . ?
C21 H21B 0.9300 . ?
C22 C23 1.377(4) . ?
C22 C27 1.379(4) . ?
C23 C24 1.375(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.365(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.371(5) . ?
C25 Cl1 1.743(3) . ?
C26 C27 1.368(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 O3 1.195(3) . ?
C28 O4 1.326(3) . ?
C29 C30 1.394(7) . ?
C29 O4 1.456(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C2 C3 C1 109.1(3) . . ?
C2 C3 C5 110.6(3) . . ?
C1 C3 C5 110.4(3) . . ?
C2 C3 C4 107.4(3) . . ?
C1 C3 C4 108.6(3) . . ?
C5 C3 C4 110.8(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 119.0(2) . . ?
C6 C5 C3 122.2(2) . . ?
C10 C5 C3 118.7(2) . . ?
C5 C6 C7 125.6(2) . . ?
C5 C6 H6 117.2 . . ?
C7 C6 H6 117.2 . . ?
C6 C7 C8 112.22(19) . . ?
C6 C7 C18 114.8(2) . . ?
C8 C7 C18 106.82(19) . . ?
C6 C7 C15 112.21(19) . . ?
C8 C7 C15 108.10(19) . . ?
C18 C7 C15 101.92(18) . . ?
C9 C8 C7 125.8(2) . . ?
C9 C8 H8 117.1 . . ?
C7 C8 H8 117.1 . . ?
C8 C9 C10 118.5(2) . . ?
C8 C9 C11 122.6(2) . . ?
C10 C9 C11 118.9(2) . . ?
O5 C10 C5 120.8(2) . . ?
O5 C10 C9 120.8(2) . . ?
C5 C10 C9 118.4(2) . . ?
C14 C11 C12 107.6(3) . . ?
C14 C11 C13 110.1(3) . . ?
C12 C11 C13 108.6(3) . . ?
C14 C11 C9 110.7(2) . . ?
C12 C11 C9 110.7(2) . . ?
C13 C11 C9 109.0(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C22 C15 C16 118.0(2) . . ?
C22 C15 C7 112.62(19) . . ?
C16 C15 C7 101.6(2) . . ?
C22 C15 H15 108.0 . . ?
C16 C15 H15 108.0 . . ?
C7 C15 H15 108.0 . . ?
C17 C16 C15 113.5(3) . . ?
C17 C16 H16 123.3 . . ?
C15 C16 H16 123.3 . . ?
C16 C17 C18 111.5(2) . . ?
C16 C17 H17 124.3 . . ?
C18 C17 H17 124.3 . . ?
C28 C18 C17 114.3(2) . . ?
C28 C18 C19 109.8(2) . . ?
C17 C18 C19 105.4(2) . . ?
C28 C18 C7 111.3(2) . . ?
C17 C18 C7 101.7(2) . . ?
C19 C18 C7 114.0(2) . . ?
O2 C19 O1 124.8(3) . . ?
O2 C19 C18 125.5(3) . . ?
O1 C19 C18 109.5(3) . . ?
C21 C20 O1 107.4(4) . . ?
C21 C20 H20A 110.2 . . ?
O1 C20 H20A 110.2 . . ?
C21 C20 H20B 110.2 . . ?
O1 C20 H20B 110.2 . . ?
H20A C20 H20B 108.5 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
C23 C22 C27 117.1(3) . . ?
C23 C22 C15 120.2(2) . . ?
C27 C22 C15 122.7(2) . . ?
C24 C23 C22 121.9(3) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 120.5(3) . . ?
C24 C25 Cl1 119.8(3) . . ?
C26 C25 Cl1 119.8(3) . . ?
C27 C26 C25 119.4(3) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C22 121.9(3) . . ?
C26 C27 H27 119.1 . . ?
C22 C27 H27 119.1 . . ?
O3 C28 O4 124.1(3) . . ?
O3 C28 C18 125.6(3) . . ?
O4 C28 C18 110.3(2) . . ?
C30 C29 O4 110.3(4) . . ?
C30 C29 H29A 109.6 . . ?
O4 C29 H29A 109.6 . . ?
C30 C29 H29B 109.6 . . ?
O4 C29 H29B 109.6 . . ?
H29A C29 H29B 108.1 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C19 O1 C20 117.2(3) . . ?
C28 O4 C29 116.7(3) . . ?

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
C2 C3 C5 C6 -123.3(3) . . . . ?
C1 C3 C5 C6 115.9(3) . . . . ?
C4 C3 C5 C6 -4.4(4) . . . . ?
C2 C3 C5 C10 58.4(4) . . . . ?
C1 C3 C5 C10 -62.4(4) . . . . ?
C4 C3 C5 C10 177.3(3) . . . . ?
C10 C5 C6 C7 -0.5(4) . . . . ?
C3 C5 C6 C7 -178.8(3) . . . . ?
C5 C6 C7 C8 -3.9(4) . . . . ?
C5 C6 C7 C18 118.3(3) . . . . ?
C5 C6 C7 C15 -125.9(3) . . . . ?
C6 C7 C8 C9 2.9(4) . . . . ?
C18 C7 C8 C9 -123.8(3) . . . . ?
C15 C7 C8 C9 127.2(3) . . . . ?
C7 C8 C9 C10 2.3(4) . . . . ?
C7 C8 C9 C11 -177.5(2) . . . . ?
C6 C5 C10 O5 -174.1(3) . . . . ?
C3 C5 C10 O5 4.2(4) . . . . ?
C6 C5 C10 C9 6.0(4) . . . . ?
C3 C5 C10 C9 -175.7(3) . . . . ?
C8 C9 C10 O5 173.3(3) . . . . ?
C11 C9 C10 O5 -7.0(4) . . . . ?
C8 C9 C10 C5 -6.8(4) . . . . ?
C11 C9 C10 C5 172.9(2) . . . . ?
C8 C9 C11 C14 -117.5(3) . . . . ?
C10 C9 C11 C14 62.8(3) . . . . ?
C8 C9 C11 C12 1.8(4) . . . . ?
C10 C9 C11 C12 -178.0(3) . . . . ?
C8 C9 C11 C13 121.2(3) . . . . ?
C10 C9 C11 C13 -58.5(4) . . . . ?
C6 C7 C15 C22 81.2(2) . . . . ?
C8 C7 C15 C22 -43.1(3) . . . . ?
C18 C7 C15 C22 -155.5(2) . . . . ?
C6 C7 C15 C16 -151.7(2) . . . . ?
C8 C7 C15 C16 84.1(2) . . . . ?
C18 C7 C15 C16 -28.3(2) . . . . ?
C22 C15 C16 C17 140.9(3) . . . . ?
C7 C15 C16 C17 17.2(3) . . . . ?
C15 C16 C17 C18 2.5(3) . . . . ?
C16 C17 C18 C28 -141.3(3) . . . . ?
C16 C17 C18 C19 98.0(3) . . . . ?
C16 C17 C18 C7 -21.2(3) . . . . ?
C6 C7 C18 C28 -86.7(3) . . . . ?
C8 C7 C18 C28 38.4(3) . . . . ?
C15 C7 C18 C28 151.7(2) . . . . ?
C6 C7 C18 C17 151.2(2) . . . . ?
C8 C7 C18 C17 -83.7(2) . . . . ?
C15 C7 C18 C17 29.6(2) . . . . ?
C6 C7 C18 C19 38.2(3) . . . . ?
C8 C7 C18 C19 163.4(2) . . . . ?
C15 C7 C18 C19 -83.3(2) . . . . ?
C28 C18 C19 O2 149.7(3) . . . . ?
C17 C18 C19 O2 -86.7(3) . . . . ?
C7 C18 C19 O2 24.1(4) . . . . ?
C28 C18 C19 O1 -34.2(3) . . . . ?
C17 C18 C19 O1 89.4(3) . . . . ?
C7 C18 C19 O1 -159.9(2) . . . . ?
C16 C15 C22 C23 157.2(3) . . . . ?
C7 C15 C22 C23 -84.9(3) . . . . ?
C16 C15 C22 C27 -24.9(4) . . . . ?
C7 C15 C22 C27 93.1(3) . . . . ?
C27 C22 C23 C24 -3.1(4) . . . . ?
C15 C22 C23 C24 175.0(3) . . . . ?
C22 C23 C24 C25 1.4(5) . . . . ?
C23 C24 C25 C26 0.7(5) . . . . ?
C23 C24 C25 Cl1 -179.0(3) . . . . ?
C24 C25 C26 C27 -1.0(5) . . . . ?
Cl1 C25 C26 C27 178.7(2) . . . . ?
C25 C26 C27 C22 -0.8(5) . . . . ?
C23 C22 C27 C26 2.7(4) . . . . ?
C15 C22 C27 C26 -175.3(3) . . . . ?
C17 C18 C28 O3 4.2(4) . . . . ?
C19 C18 C28 O3 122.5(3) . . . . ?
C7 C18 C28 O3 -110.3(3) . . . . ?
C17 C18 C28 O4 -177.1(2) . . . . ?
C19 C18 C28 O4 -58.8(3) . . . . ?
C7 C18 C28 O4 68.4(3) . . . . ?
O2 C19 O1 C20 0.9(5) . . . . ?
C18 C19 O1 C20 -175.2(3) . . . . ?
C21 C20 O1 C19 -106.6(5) . . . . ?
O3 C28 O4 C29 -2.7(5) . . . . ?
C18 C28 O4 C29 178.6(3) . . . . ?
C30 C29 O4 C28 178.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.044
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/n-hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1439295'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H40 O5'
_chemical_formula_weight         504.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.654(3)
_cell_length_b                   21.405(5)
_cell_length_c                   11.307(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.659(4)
_cell_angle_gamma                90
_cell_volume                     3035.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3120
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      25.32

_exptl_crystal_description       colorless
_exptl_crystal_colour            block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16889
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.882
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5351
_reflns_number_gt                3588
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1202P)²+0.9396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.042(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5351
_refine_ls_number_parameters     345
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.2143
_refine_ls_wR_factor_gt          0.1822
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1600(3) -0.17162(15) 0.2725(3) 0.0789(9) Uani 1 1 d . . . . .
H1A H 0.1614 -0.1583 0.1944 0.095 Uiso 1 1 calc R U . . .
C2 C 0.0793(3) -0.21073(17) 0.2976(4) 0.0950(11) Uani 1 1 d . . . . .
H2A H 0.0278 -0.2242 0.2365 0.114 Uiso 1 1 calc R U . . .
C3 C 0.0749(3) -0.22975(17) 0.4122(5) 0.0974(12) Uani 1 1 d . . . . .
H3A H 0.0197 -0.2554 0.4297 0.117 Uiso 1 1 calc R U . . .
C4 C 0.1514(4) -0.21108(19) 0.4999(4) 0.1065(13) Uani 1 1 d . . . . .
H4A H 0.1489 -0.2242 0.5779 0.128 Uiso 1 1 calc R U . . .
C5 C 0.2332(3) -0.17267(16) 0.4751(3) 0.0865(10) Uani 1 1 d . . . . .
H5A H 0.2856 -0.1607 0.5364 0.104 Uiso 1 1 calc R U . . .
C6 C 0.2383(2) -0.15188(12) 0.3607(2) 0.0585(7) Uani 1 1 d . . . . .
C7 C 0.3260(2) -0.11051(12) 0.3385(2) 0.0564(7) Uani 1 1 d . . . . .
H7A H 0.3836 -0.1084 0.3987 0.068 Uiso 1 1 calc R U . . .
C8 C 0.3327(2) -0.07605(11) 0.2438(2) 0.0542(6) Uani 1 1 d . . . . .
H8A H 0.2773 -0.0796 0.1813 0.065 Uiso 1 1 calc R U . . .
C9 C 0.42064(19) -0.03174(10) 0.2265(2) 0.0476(6) Uani 1 1 d . . . . .
H9A H 0.4479 -0.0428 0.1521 0.057 Uiso 1 1 calc R U . . .
C10 C 0.51294(19) -0.02779(12) 0.3232(2) 0.0531(6) Uani 1 1 d . . . . .
H10A H 0.5427 -0.0623 0.3651 0.064 Uiso 1 1 calc R U . . .
C11 C 0.54763(19) 0.02954(12) 0.3429(2) 0.0537(6) Uani 1 1 d . . . . .
H11A H 0.6033 0.0404 0.4016 0.064 Uiso 1 1 calc R U . . .
C12 C 0.48718(18) 0.07556(11) 0.2599(2) 0.0460(6) Uani 1 1 d . . . . .
C13 C 0.38087(18) 0.03813(10) 0.21624(18) 0.0424(5) Uani 1 1 d . . . . .
C14 C 0.30740(18) 0.04840(11) 0.3081(2) 0.0453(6) Uani 1 1 d . . . . .
H14A H 0.3298 0.0337 0.3847 0.054 Uiso 1 1 calc R U . . .
C15 C 0.21379(19) 0.07641(11) 0.2899(2) 0.0486(6) Uani 1 1 d . . . . .
C16 C 0.1777(2) 0.10122(14) 0.1683(2) 0.0647(8) Uani 1 1 d . . . . .
C17 C 0.23624(19) 0.08220(11) 0.0684(2) 0.0492(6) Uani 1 1 d . . . . .
C18 C 0.32939(19) 0.05373(11) 0.0938(2) 0.0470(6) Uani 1 1 d . . . . .
H18A H 0.3653 0.0427 0.0303 0.056 Uiso 1 1 calc R U . . .
C19 C 0.1426(2) 0.08539(14) 0.3880(2) 0.0641(7) Uani 1 1 d . . . . .
C20 C 0.1368(4) 0.1542(2) 0.4177(5) 0.140(2) Uani 1 1 d . . . . .
H20A H 0.2074 0.1699 0.4424 0.210 Uiso 1 1 calc R U . . .
H20B H 0.1051 0.1767 0.3485 0.210 Uiso 1 1 calc R U . . .
H20C H 0.0943 0.1597 0.4812 0.210 Uiso 1 1 calc R U . . .
C21 C 0.0325(3) 0.0594(3) 0.3489(4) 0.1231(17) Uani 1 1 d . . . . .
H21A H 0.0377 0.0158 0.3304 0.185 Uiso 1 1 calc R U . . .
H21B H -0.0106 0.0645 0.4120 0.185 Uiso 1 1 calc R U . . .
H21C H 0.0003 0.0814 0.2793 0.185 Uiso 1 1 calc R U . . .
C22 C 0.1864(3) 0.0499(2) 0.5005(3) 0.1020(13) Uani 1 1 d . . . . .
H22A H 0.1904 0.0062 0.4826 0.153 Uiso 1 1 calc R U . . .
H22B H 0.2564 0.0652 0.5297 0.153 Uiso 1 1 calc R U . . .
H22C H 0.1402 0.0559 0.5603 0.153 Uiso 1 1 calc R U . . .
C23 C 0.1892(2) 0.09882(13) -0.0596(2) 0.0644(7) Uani 1 1 d . . . . .
C24 C 0.0769(3) 0.0723(2) -0.0884(4) 0.1214(16) Uani 1 1 d . . . . .
H24A H 0.0330 0.0881 -0.0322 0.182 Uiso 1 1 calc R U . . .
H24B H 0.0474 0.0845 -0.1676 0.182 Uiso 1 1 calc R U . . .
H24C H 0.0797 0.0275 -0.0835 0.182 Uiso 1 1 calc R U . . .
C25 C 0.1864(3) 0.16989(16) -0.0739(3) 0.0917(11) Uani 1 1 d . . . . .
H25A H 0.2573 0.1863 -0.0556 0.138 Uiso 1 1 calc R U . . .
H25B H 0.1584 0.1804 -0.1545 0.138 Uiso 1 1 calc R U . . .
H25C H 0.1416 0.1876 -0.0204 0.138 Uiso 1 1 calc R U . . .
C26 C 0.2585(4) 0.0736(2) -0.1491(3) 0.1074(14) Uani 1 1 d . . . . .
H26A H 0.3293 0.0902 -0.1313 0.161 Uiso 1 1 calc R U . . .
H26B H 0.2611 0.0288 -0.1441 0.161 Uiso 1 1 calc R U . . .
H26C H 0.2288 0.0858 -0.2282 0.161 Uiso 1 1 calc R U . . .
C27 C 0.4625(2) 0.13678(11) 0.3194(2) 0.0518(6) Uani 1 1 d . . . . .
C28 C 0.3923(3) 0.23823(14) 0.2777(3) 0.0909(11) Uani 0.533(12) 1 d . . P A 1
H28A H 0.3248 0.2519 0.2349 0.109 Uiso 0.533(12) 1 calc R U P A 1
H28B H 0.3857 0.2371 0.3621 0.109 Uiso 0.533(12) 1 calc R U P A 1
C28' C 0.3923(3) 0.23823(14) 0.2777(3) 0.0909(11) Uani 0.467(12) 1 d . . P A 2
H28C H 0.3276 0.2367 0.3149 0.109 Uiso 0.467(12) 1 calc R U P A 2
H28D H 0.4497 0.2533 0.3362 0.109 Uiso 0.467(12) 1 calc R U P A 2
C30 C 0.5573(2) 0.08991(12) 0.1626(2) 0.0535(6) Uani 1 1 d . . . . .
C31 C 0.7001(3) 0.15503(19) 0.1171(4) 0.1032(13) Uani 1 1 d . . . . .
H31A H 0.6642 0.1527 0.0358 0.124 Uiso 1 1 calc R U . . .
H31B H 0.7200 0.1982 0.1340 0.124 Uiso 1 1 calc R U . . .
C32 C 0.7927(5) 0.1170(3) 0.1290(7) 0.189(3) Uani 1 1 d . . . . .
H32A H 0.8397 0.1311 0.0745 0.283 Uiso 1 1 calc R U . . .
H32B H 0.8284 0.1198 0.2092 0.283 Uiso 1 1 calc R U . . .
H32C H 0.7727 0.0744 0.1112 0.283 Uiso 1 1 calc R U . . .
O1 O 0.1021(2) 0.13639(16) 0.1514(2) 0.1354(13) Uani 1 1 d . . . . .
O2 O 0.47956(18) 0.14707(9) 0.42403(17) 0.0756(6) Uani 1 1 d . . . . .
O3 O 0.41767(16) 0.17654(8) 0.23782(16) 0.0636(5) Uani 1 1 d . . . . .
O4 O 0.55463(17) 0.06411(11) 0.06969(18) 0.0841(7) Uani 1 1 d . . . . .
O5 O 0.62735(16) 0.13357(10) 0.20069(19) 0.0792(6) Uani 1 1 d . . . . .
C29 C 0.4746(10) 0.2812(4) 0.2570(12) 0.150(5) Uani 0.533(12) 1 d . U P A 1
H29A H 0.4574 0.3221 0.2837 0.225 Uiso 0.533(12) 1 calc R U P A 1
H29B H 0.5413 0.2678 0.3002 0.225 Uiso 0.533(12) 1 calc R U P A 1
H29C H 0.4805 0.2825 0.1733 0.225 Uiso 0.533(12) 1 calc R U P A 1
C29' C 0.3784(12) 0.2784(4) 0.1801(9) 0.122(4) Uani 0.467(12) 1 d . U P A 2
H29D H 0.3616 0.3195 0.2061 0.183 Uiso 0.467(12) 1 calc R U P A 2
H29E H 0.4429 0.2800 0.1441 0.183 Uiso 0.467(12) 1 calc R U P A 2
H29F H 0.3212 0.2634 0.1228 0.183 Uiso 0.467(12) 1 calc R U P A 2


_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 C6 1.376(4) . ?
C1 C2 1.379(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.366(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.350(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.377(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.467(4) . ?
C7 C8 1.313(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.494(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.492(3) . ?
C9 C13 1.577(3) . ?
C9 H9A 0.9800 . ?
C10 C11 1.312(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.498(3) . ?
C11 H11A 0.9300 . ?
C12 C27 1.524(3) . ?
C12 C30 1.533(3) . ?
C12 C13 1.587(3) . ?
C13 C18 1.488(3) . ?
C13 C14 1.499(3) . ?
C14 C15 1.319(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.488(4) . ?
C15 C19 1.531(3) . ?
C16 O1 1.213(3) . ?
C16 C17 1.488(4) . ?
C17 C18 1.324(3) . ?
C17 C23 1.532(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.515(5) . ?
C19 C21 1.511(4) . ?
C19 C22 1.522(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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 C24 1.524(5) . ?
C23 C26 1.524(5) . ?
C23 C25 1.530(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 O2 1.194(3) . ?
C27 O3 1.326(3) . ?
C28 C29 1.432(10) . ?
C28 O3 1.445(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28' C29' 1.391(9) . ?
C28' O3 1.445(3) . ?
C28' H28C 0.9700 . ?
C28' H28D 0.9700 . ?
C30 O4 1.183(3) . ?
C30 O5 1.320(3) . ?
C31 C32 1.419(6) . ?
C31 O5 1.478(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C29' H29D 0.9600 . ?
C29' H29E 0.9600 . ?
C29' H29F 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
C6 C1 C2 121.2(3) . . ?
C6 C1 H1A 119.4 . . ?
C2 C1 H1A 119.4 . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C1 C6 C5 117.5(3) . . ?
C1 C6 C7 123.3(3) . . ?
C5 C6 C7 119.2(3) . . ?
C8 C7 C6 127.7(3) . . ?
C8 C7 H7A 116.1 . . ?
C6 C7 H7A 116.1 . . ?
C7 C8 C9 126.4(2) . . ?
C7 C8 H8A 116.8 . . ?
C9 C8 H8A 116.8 . . ?
C10 C9 C8 117.6(2) . . ?
C10 C9 C13 102.19(18) . . ?
C8 C9 C13 112.06(19) . . ?
C10 C9 H9A 108.2 . . ?
C8 C9 H9A 108.2 . . ?
C13 C9 H9A 108.2 . . ?
C11 C10 C9 112.9(2) . . ?
C11 C10 H10A 123.6 . . ?
C9 C10 H10A 123.6 . . ?
C10 C11 C12 112.1(2) . . ?
C10 C11 H11A 123.9 . . ?
C12 C11 H11A 123.9 . . ?
C11 C12 C27 113.9(2) . . ?
C11 C12 C30 106.58(19) . . ?
C27 C12 C30 108.5(2) . . ?
C11 C12 C13 101.77(18) . . ?
C27 C12 C13 110.88(18) . . ?
C30 C12 C13 115.18(18) . . ?
C18 C13 C14 112.13(19) . . ?
C18 C13 C9 112.16(18) . . ?
C14 C13 C9 108.01(18) . . ?
C18 C13 C12 115.09(18) . . ?
C14 C13 C12 106.79(17) . . ?
C9 C13 C12 101.94(17) . . ?
C15 C14 C13 125.8(2) . . ?
C15 C14 H14A 117.1 . . ?
C13 C14 H14A 117.1 . . ?
C14 C15 C16 117.7(2) . . ?
C14 C15 C19 123.2(2) . . ?
C16 C15 C19 119.1(2) . . ?
O1 C16 C15 120.4(3) . . ?
O1 C16 C17 120.8(3) . . ?
C15 C16 C17 118.8(2) . . ?
C18 C17 C16 118.7(2) . . ?
C18 C17 C23 122.3(2) . . ?
C16 C17 C23 118.9(2) . . ?
C17 C18 C13 124.9(2) . . ?
C17 C18 H18A 117.6 . . ?
C13 C18 H18A 117.6 . . ?
C20 C19 C21 110.7(4) . . ?
C20 C19 C22 108.8(3) . . ?
C21 C19 C22 106.3(3) . . ?
C20 C19 C15 109.5(3) . . ?
C21 C19 C15 110.5(2) . . ?
C22 C19 C15 111.0(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C26 109.2(3) . . ?
C24 C23 C25 109.9(3) . . ?
C26 C23 C25 106.9(3) . . ?
C24 C23 C17 110.4(2) . . ?
C26 C23 C17 111.1(2) . . ?
C25 C23 C17 109.3(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O2 C27 O3 125.1(2) . . ?
O2 C27 C12 125.1(2) . . ?
O3 C27 C12 109.8(2) . . ?
C29 C28 O3 109.9(5) . . ?
C29 C28 H28A 109.7 . . ?
O3 C28 H28A 109.7 . . ?
C29 C28 H28B 109.7 . . ?
O3 C28 H28B 109.7 . . ?
H28A C28 H28B 108.2 . . ?
C29' C28' O3 109.1(4) . . ?
C29' C28' H28C 109.9 . . ?
O3 C28' H28C 109.9 . . ?
C29' C28' H28D 109.9 . . ?
O3 C28' H28D 109.9 . . ?
H28C C28' H28D 108.3 . . ?
O4 C30 O5 123.9(2) . . ?
O4 C30 C12 126.4(2) . . ?
O5 C30 C12 109.6(2) . . ?
C32 C31 O5 109.8(4) . . ?
C32 C31 H31A 109.7 . . ?
O5 C31 H31A 109.7 . . ?
C32 C31 H31B 109.7 . . ?
O5 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C27 O3 C28' 117.5(2) . . ?
C27 O3 C28 117.5(2) . . ?
C30 O5 C31 117.4(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28' C29' H29D 109.5 . . ?
C28' C29' H29E 109.5 . . ?
H29D C29' H29E 109.5 . . ?
C28' C29' H29F 109.5 . . ?
H29D C29' H29F 109.5 . . ?
H29E C29' H29F 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
C6 C1 C2 C3 1.2(5) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
C2 C1 C6 C7 179.8(3) . . . . ?
C4 C5 C6 C1 -1.0(5) . . . . ?
C4 C5 C6 C7 179.3(3) . . . . ?
C1 C6 C7 C8 15.7(4) . . . . ?
C5 C6 C7 C8 -164.6(3) . . . . ?
C6 C7 C8 C9 176.5(2) . . . . ?
C7 C8 C9 C10 3.0(4) . . . . ?
C7 C8 C9 C13 -115.0(3) . . . . ?
C8 C9 C10 C11 -140.4(2) . . . . ?
C13 C9 C10 C11 -17.2(3) . . . . ?
C9 C10 C11 C12 -1.9(3) . . . . ?
C10 C11 C12 C27 139.4(2) . . . . ?
C10 C11 C12 C30 -101.1(2) . . . . ?
C10 C11 C12 C13 20.0(3) . . . . ?
C10 C9 C13 C18 151.11(19) . . . . ?
C8 C9 C13 C18 -82.1(2) . . . . ?
C10 C9 C13 C14 -84.8(2) . . . . ?
C8 C9 C13 C14 42.0(2) . . . . ?
C10 C9 C13 C12 27.5(2) . . . . ?
C8 C9 C13 C12 154.29(19) . . . . ?
C11 C12 C13 C18 -150.02(19) . . . . ?
C27 C12 C13 C18 88.4(2) . . . . ?
C30 C12 C13 C18 -35.2(3) . . . . ?
C11 C12 C13 C14 84.8(2) . . . . ?
C27 C12 C13 C14 -36.7(2) . . . . ?
C30 C12 C13 C14 -160.34(19) . . . . ?
C11 C12 C13 C9 -28.4(2) . . . . ?
C27 C12 C13 C9 -149.92(18) . . . . ?
C30 C12 C13 C9 86.5(2) . . . . ?
C18 C13 C14 C15 -9.6(3) . . . . ?
C9 C13 C14 C15 -133.7(2) . . . . ?
C12 C13 C14 C15 117.3(3) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C13 C14 C15 C19 -180.0(2) . . . . ?
C14 C15 C16 O1 -167.3(3) . . . . ?
C19 C15 C16 O1 11.6(4) . . . . ?
C14 C15 C16 C17 12.5(4) . . . . ?
C19 C15 C16 C17 -168.6(2) . . . . ?
O1 C16 C17 C18 167.4(3) . . . . ?
C15 C16 C17 C18 -12.5(4) . . . . ?
O1 C16 C17 C23 -9.9(4) . . . . ?
C15 C16 C17 C23 170.2(2) . . . . ?
C16 C17 C18 C13 0.8(4) . . . . ?
C23 C17 C18 C13 178.0(2) . . . . ?
C14 C13 C18 C17 9.7(3) . . . . ?
C9 C13 C18 C17 131.4(2) . . . . ?
C12 C13 C18 C17 -112.6(3) . . . . ?
C14 C15 C19 C20 111.9(4) . . . . ?
C16 C15 C19 C20 -67.0(4) . . . . ?
C14 C15 C19 C21 -126.0(3) . . . . ?
C16 C15 C19 C21 55.2(4) . . . . ?
C14 C15 C19 C22 -8.3(4) . . . . ?
C16 C15 C19 C22 172.8(3) . . . . ?
C18 C17 C23 C24 126.0(3) . . . . ?
C16 C17 C23 C24 -56.8(4) . . . . ?
C18 C17 C23 C26 4.7(4) . . . . ?
C16 C17 C23 C26 -178.1(3) . . . . ?
C18 C17 C23 C25 -113.0(3) . . . . ?
C16 C17 C23 C25 64.2(3) . . . . ?
C11 C12 C27 O2 -6.6(4) . . . . ?
C30 C12 C27 O2 -125.1(3) . . . . ?
C13 C12 C27 O2 107.5(3) . . . . ?
C11 C12 C27 O3 174.4(2) . . . . ?
C30 C12 C27 O3 55.9(3) . . . . ?
C13 C12 C27 O3 -71.5(2) . . . . ?
C11 C12 C30 O4 92.4(3) . . . . ?
C27 C12 C30 O4 -144.6(3) . . . . ?
C13 C12 C30 O4 -19.7(4) . . . . ?
C11 C12 C30 O5 -83.7(2) . . . . ?
C27 C12 C30 O5 39.4(3) . . . . ?
C13 C12 C30 O5 164.3(2) . . . . ?
O2 C27 O3 C28' 3.3(4) . . . . ?
C12 C27 O3 C28' -177.7(2) . . . . ?
O2 C27 O3 C28 3.3(4) . . . . ?
C12 C27 O3 C28 -177.7(2) . . . . ?
C29' C28' O3 C27 161.4(7) . . . . ?
C29 C28 O3 C27 98.0(7) . . . . ?
O4 C30 O5 C31 5.7(4) . . . . ?
C12 C30 O5 C31 -178.1(3) . . . . ?
C32 C31 O5 C30 -88.6(5) . . . . ?

_refine_diff_density_max         0.675
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.046



