# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# 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_dm13056_0m
_database_code_depnum_ccdc_archive 'CCDC 928251'
_audit_update_record             
;
2013-03-07 deposited with the CCDC.
2014-12-08 downloaded from the CCDC.
;
#TrackingRef 'cu_dm13056_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H42 O2'
_chemical_formula_weight         410.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   8.5312(2)
_cell_length_b                   11.5963(2)
_cell_length_c                   24.0459(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2378.87(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9885
_cell_measurement_theta_min      5.18
_cell_measurement_theta_max      69.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8658
_exptl_absorpt_correction_T_max  0.9343
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18693
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         4.23
_diffrn_reflns_theta_max         69.65
_reflns_number_total             4410
_reflns_number_gt                4357
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0935P)²+0.0000P] 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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4410
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002

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
O1 O 0.46063(15) 0.69760(10) 0.25613(4) 0.0502(3) Uani 1 1 d . . .
O2 O 0.60866(12) 1.29517(8) 0.02292(4) 0.0368(2) Uani 1 1 d . . .
C1 C 0.59199(19) 0.72713(12) 0.21983(5) 0.0366(3) Uani 1 1 d . . .
H1 H 0.6576 0.6596 0.2086 0.044 Uiso 1 1 calc R . .
C2 C 0.68501(17) 0.83377(12) 0.23371(5) 0.0350(3) Uani 1 1 d . . .
H2A H 0.7400 0.8222 0.2695 0.042 Uiso 1 1 calc R . .
H2B H 0.6127 0.8999 0.2381 0.042 Uiso 1 1 calc R . .
C3 C 0.80615(14) 0.86158(10) 0.18794(5) 0.0263(3) Uani 1 1 d . . .
H3A H 0.8787 0.9219 0.2016 0.032 Uiso 1 1 calc R . .
H3B H 0.8686 0.7916 0.1799 0.032 Uiso 1 1 calc R . .
C4 C 0.72868(13) 0.90301(9) 0.13477(4) 0.0200(2) Uani 1 1 d . . .
C5 C 0.68263(13) 0.82886(9) 0.09535(5) 0.0207(2) Uani 1 1 d . . .
H5 H 0.6182 0.8588 0.0665 0.025 Uiso 1 1 calc R . .
C6 C 0.72251(13) 0.70427(9) 0.09225(5) 0.0231(2) Uani 1 1 d . . .
H6 H 0.8237 0.6833 0.1107 0.028 Uiso 1 1 calc R . .
C7 C 0.59937(15) 0.60768(10) 0.09246(5) 0.0278(3) Uani 1 1 d . . .
H7 H 0.6368 0.5354 0.1108 0.033 Uiso 1 1 calc R . .
C8 C 0.42745(15) 0.63057(12) 0.10157(5) 0.0324(3) Uani 1 1 d . . .
H8A H 0.3653 0.5744 0.0798 0.039 Uiso 1 1 calc R . .
H8B H 0.4018 0.7087 0.0878 0.039 Uiso 1 1 calc R . .
C9 C 0.38099(18) 0.62163(14) 0.16327(5) 0.0413(3) Uani 1 1 d . . .
H9A H 0.2657 0.6136 0.1658 0.050 Uiso 1 1 calc R . .
H9B H 0.4284 0.5510 0.1791 0.050 Uiso 1 1 calc R . .
C10 C 0.43141(18) 0.72426(13) 0.19788(5) 0.0372(3) Uani 1 1 d . . .
C11 C 0.68708(14) 0.63576(10) 0.03974(5) 0.0272(3) Uani 1 1 d . . .
C12 C 0.81007(18) 0.54895(12) 0.02185(7) 0.0423(4) Uani 1 1 d . . .
H12A H 0.8589 0.5147 0.0548 0.063 Uiso 1 1 calc R . .
H12B H 0.8903 0.5878 -0.0005 0.063 Uiso 1 1 calc R . .
H12C H 0.7605 0.4882 -0.0004 0.063 Uiso 1 1 calc R . .
C13 C 0.60582(16) 0.69534(11) -0.00832(5) 0.0316(3) Uani 1 1 d . . .
H13A H 0.5832 0.6389 -0.0376 0.047 Uiso 1 1 calc R . .
H13B H 0.6741 0.7559 -0.0232 0.047 Uiso 1 1 calc R . .
H13C H 0.5076 0.7298 0.0047 0.047 Uiso 1 1 calc R . .
C14 C 0.33476(18) 0.83101(15) 0.18893(6) 0.0443(4) Uani 1 1 d . . .
H14A H 0.2245 0.8141 0.1969 0.066 Uiso 1 1 calc R . .
H14B H 0.3451 0.8564 0.1502 0.066 Uiso 1 1 calc R . .
H14C H 0.3716 0.8922 0.2138 0.066 Uiso 1 1 calc R . .
C1' C 0.70416(12) 1.03357(9) 0.12896(4) 0.0185(2) Uani 1 1 d . . .
H1' H 0.7190 1.0681 0.1667 0.022 Uiso 1 1 calc R . .
C2' C 0.53668(13) 1.06310(10) 0.11012(5) 0.0246(2) Uani 1 1 d . . .
H2'1 H 0.4617 1.0342 0.1383 0.030 Uiso 1 1 calc R . .
H2'2 H 0.5147 1.0226 0.0747 0.030 Uiso 1 1 calc R . .
C3' C 0.50948(13) 1.19327(11) 0.10176(5) 0.0268(3) Uani 1 1 d . . .
H3'1 H 0.4064 1.2058 0.0838 0.032 Uiso 1 1 calc R . .
H3'2 H 0.5082 1.2323 0.1384 0.032 Uiso 1 1 calc R . .
C4' C 0.63606(14) 1.24423(9) 0.06627(5) 0.0243(2) Uani 1 1 d . . .
C5' C 0.80148(12) 1.22321(9) 0.08599(4) 0.0183(2) Uani 1 1 d . . .
H5' H 0.8747 1.2550 0.0574 0.022 Uiso 1 1 calc R . .
C6' C 0.83188(12) 1.28629(9) 0.14053(4) 0.0191(2) Uani 1 1 d . . .
H6' H 0.7361 1.3190 0.1586 0.023 Uiso 1 1 calc R . .
C7' C 0.95318(13) 1.23895(9) 0.18069(4) 0.0197(2) Uani 1 1 d . . .
H7' H 0.9236 1.2463 0.2208 0.024 Uiso 1 1 calc R . .
C8' C 1.04037(13) 1.12874(9) 0.16656(4) 0.0228(2) Uani 1 1 d . . .
H8'1 H 1.0203 1.0719 0.1965 0.027 Uiso 1 1 calc R . .
H8'2 H 1.1541 1.1456 0.1667 0.027 Uiso 1 1 calc R . .
C9' C 0.99852(12) 1.07223(9) 0.11036(4) 0.0210(2) Uani 1 1 d . . .
H9'1 H 1.0181 0.9883 0.1135 0.025 Uiso 1 1 calc R . .
H9'2 H 1.0709 1.1027 0.0818 0.025 Uiso 1 1 calc R . .
C10' C 0.82896(12) 1.08985(9) 0.08958(4) 0.0183(2) Uani 1 1 d . . .
C11' C 0.98124(13) 1.35306(9) 0.15161(4) 0.0207(2) Uani 1 1 d . . .
C12' C 1.11059(13) 1.36197(10) 0.10864(5) 0.0249(2) Uani 1 1 d . . .
H12D H 1.1116 1.2921 0.0857 0.037 Uiso 1 1 calc R . .
H12E H 1.2118 1.3703 0.1275 0.037 Uiso 1 1 calc R . .
H12F H 1.0920 1.4293 0.0849 0.037 Uiso 1 1 calc R . .
C13' C 0.96265(15) 1.46130(10) 0.18618(5) 0.0254(2) Uani 1 1 d . . .
H13D H 0.9348 1.5260 0.1619 0.038 Uiso 1 1 calc R . .
H13E H 1.0615 1.4783 0.2052 0.038 Uiso 1 1 calc R . .
H13F H 0.8796 1.4497 0.2138 0.038 Uiso 1 1 calc R . .
C14' C 0.81848(14) 1.04267(10) 0.03003(4) 0.0226(2) Uani 1 1 d . . .
H14D H 0.8948 1.0826 0.0064 0.034 Uiso 1 1 calc R . .
H14E H 0.7126 1.0554 0.0155 0.034 Uiso 1 1 calc R . .
H14F H 0.8413 0.9598 0.0302 0.034 Uiso 1 1 calc R . .


_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 C10 1.4561(16) . ?
O1 C1 1.4613(17) . ?
O2 C4' 1.2208(14) . ?
C1 C10 1.469(2) . ?
C1 C2 1.5067(18) . ?
C1 H1 1.0000 . ?
C2 C3 1.5438(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5173(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.3388(16) . ?
C4 C1' 1.5348(14) . ?
C5 C6 1.4862(14) . ?
C5 H5 0.9500 . ?
C6 C11 1.5221(15) . ?
C6 C7 1.5357(15) . ?
C6 H6 1.0000 . ?
C7 C8 1.5065(18) . ?
C7 C11 1.5076(16) . ?
C7 H7 1.0000 . ?
C8 C9 1.5390(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5146(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C14 1.503(2) . ?
C11 C13 1.5144(18) . ?
C11 C12 1.5164(17) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C1' C2' 1.5376(14) . ?
C1' C10' 1.5673(14) . ?
C1' H1' 1.0000 . ?
C2' C3' 1.5403(16) . ?
C2' H2'1 0.9900 . ?
C2' H2'2 0.9900 . ?
C3' C4' 1.4979(17) . ?
C3' H3'1 0.9900 . ?
C3' H3'2 0.9900 . ?
C4' C5' 1.5086(15) . ?
C5' C6' 1.5239(14) . ?
C5' C10' 1.5665(13) . ?
C5' H5' 1.0000 . ?
C6' C11' 1.5146(14) . ?
C6' C7' 1.5182(14) . ?
C6' H6' 1.0000 . ?
C7' C11' 1.5157(14) . ?
C7' C8' 1.5173(15) . ?
C7' H7' 1.0000 . ?
C8' C9' 1.5438(14) . ?
C8' H8'1 0.9900 . ?
C8' H8'2 0.9900 . ?
C9' C10' 1.5440(14) . ?
C9' H9'1 0.9900 . ?
C9' H9'2 0.9900 . ?
C10' C14' 1.5356(13) . ?
C11' C13' 1.5138(15) . ?
C11' C12' 1.5152(14) . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 0.9800 . ?
C13' H13D 0.9800 . ?
C13' H13E 0.9800 . ?
C13' H13F 0.9800 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 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
C10 O1 C1 60.45(9) . . ?
O1 C1 C10 59.60(9) . . ?
O1 C1 C2 117.64(11) . . ?
C10 C1 C2 126.13(13) . . ?
O1 C1 H1 114.1 . . ?
C10 C1 H1 114.1 . . ?
C2 C1 H1 114.1 . . ?
C1 C2 C3 111.47(10) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 112.04(10) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 121.41(10) . . ?
C5 C4 C1' 121.94(10) . . ?
C3 C4 C1' 116.65(9) . . ?
C4 C5 C6 126.35(10) . . ?
C4 C5 H5 116.8 . . ?
C6 C5 H5 116.8 . . ?
C5 C6 C11 120.23(10) . . ?
C5 C6 C7 123.53(10) . . ?
C11 C6 C7 59.08(7) . . ?
C5 C6 H6 114.3 . . ?
C11 C6 H6 114.3 . . ?
C7 C6 H6 114.3 . . ?
C8 C7 C11 124.57(12) . . ?
C8 C7 C6 122.54(11) . . ?
C11 C7 C6 60.01(7) . . ?
C8 C7 H7 113.2 . . ?
C11 C7 H7 113.2 . . ?
C6 C7 H7 113.2 . . ?
C7 C8 C9 112.27(12) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 113.80(11) . . ?
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 . . ?
O1 C10 C1 59.95(9) . . ?
O1 C10 C14 113.98(12) . . ?
C1 C10 C14 122.99(12) . . ?
O1 C10 C9 114.23(12) . . ?
C1 C10 C9 118.70(14) . . ?
C14 C10 C9 114.38(13) . . ?
C7 C11 C13 120.86(11) . . ?
C7 C11 C12 116.01(11) . . ?
C13 C11 C12 113.77(11) . . ?
C7 C11 C6 60.91(7) . . ?
C13 C11 C6 119.07(10) . . ?
C12 C11 C6 116.39(11) . . ?
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 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C1' C2' 111.92(9) . . ?
C4 C1' C10' 111.92(9) . . ?
C2' C1' C10' 111.13(8) . . ?
C4 C1' H1' 107.2 . . ?
C2' C1' H1' 107.2 . . ?
C10' C1' H1' 107.2 . . ?
C1' C2' C3' 113.37(9) . . ?
C1' C2' H2'1 108.9 . . ?
C3' C2' H2'1 108.9 . . ?
C1' C2' H2'2 108.9 . . ?
C3' C2' H2'2 108.9 . . ?
H2'1 C2' H2'2 107.7 . . ?
C4' C3' C2' 110.63(10) . . ?
C4' C3' H3'1 109.5 . . ?
C2' C3' H3'1 109.5 . . ?
C4' C3' H3'2 109.5 . . ?
C2' C3' H3'2 109.5 . . ?
H3'1 C3' H3'2 108.1 . . ?
O2 C4' C3' 122.64(11) . . ?
O2 C4' C5' 121.71(11) . . ?
C3' C4' C5' 115.57(9) . . ?
C4' C5' C6' 110.62(9) . . ?
C4' C5' C10' 108.47(8) . . ?
C6' C5' C10' 113.64(8) . . ?
C4' C5' H5' 108.0 . . ?
C6' C5' H5' 108.0 . . ?
C10' C5' H5' 108.0 . . ?
C11' C6' C7' 59.97(7) . . ?
C11' C6' C5' 122.68(9) . . ?
C7' C6' C5' 119.33(9) . . ?
C11' C6' H6' 114.7 . . ?
C7' C6' H6' 114.7 . . ?
C5' C6' H6' 114.7 . . ?
C11' C7' C8' 123.69(9) . . ?
C11' C7' C6' 59.90(7) . . ?
C8' C7' C6' 119.75(9) . . ?
C11' C7' H7' 114.3 . . ?
C8' C7' H7' 114.3 . . ?
C6' C7' H7' 114.3 . . ?
C7' C8' C9' 116.12(9) . . ?
C7' C8' H8'1 108.3 . . ?
C9' C8' H8'1 108.3 . . ?
C7' C8' H8'2 108.3 . . ?
C9' C8' H8'2 108.3 . . ?
H8'1 C8' H8'2 107.4 . . ?
C8' C9' C10' 116.35(9) . . ?
C8' C9' H9'1 108.2 . . ?
C10' C9' H9'1 108.2 . . ?
C8' C9' H9'2 108.2 . . ?
C10' C9' H9'2 108.2 . . ?
H9'1 C9' H9'2 107.4 . . ?
C14' C10' C9' 108.01(9) . . ?
C14' C10' C1' 112.05(8) . . ?
C9' C10' C1' 112.69(8) . . ?
C14' C10' C5' 106.96(8) . . ?
C9' C10' C5' 106.78(8) . . ?
C1' C10' C5' 110.05(8) . . ?
C6' C11' C13' 115.61(9) . . ?
C6' C11' C12' 121.84(9) . . ?
C13' C11' C12' 113.22(9) . . ?
C6' C11' C7' 60.13(7) . . ?
C13' C11' C7' 116.99(9) . . ?
C12' C11' C7' 119.28(9) . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C11' C13' H13D 109.5 . . ?
C11' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C11' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C10' C14' H14D 109.5 . . ?
C10' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C10' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 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
C10 O1 C1 C2 117.68(15) . . . . ?
O1 C1 C2 C3 -173.10(12) . . . . ?
C10 C1 C2 C3 -102.07(16) . . . . ?
C1 C2 C3 C4 70.10(14) . . . . ?
C2 C3 C4 C5 -88.45(14) . . . . ?
C2 C3 C4 C1' 90.79(12) . . . . ?
C3 C4 C5 C6 -11.27(19) . . . . ?
C1' C4 C5 C6 169.52(11) . . . . ?
C4 C5 C6 C11 -168.73(11) . . . . ?
C4 C5 C6 C7 120.37(13) . . . . ?
C5 C6 C7 C8 -6.24(18) . . . . ?
C11 C6 C7 C8 -114.13(14) . . . . ?
C5 C6 C7 C11 107.89(12) . . . . ?
C11 C7 C8 C9 -165.52(12) . . . . ?
C6 C7 C8 C9 -91.81(15) . . . . ?
C7 C8 C9 C10 75.56(17) . . . . ?
C1 O1 C10 C14 -115.54(14) . . . . ?
C1 O1 C10 C9 110.37(15) . . . . ?
C2 C1 C10 O1 -103.74(14) . . . . ?
O1 C1 C10 C14 100.62(13) . . . . ?
C2 C1 C10 C14 -3.12(19) . . . . ?
O1 C1 C10 C9 -102.94(13) . . . . ?
C2 C1 C10 C9 153.32(12) . . . . ?
C8 C9 C10 O1 -151.32(13) . . . . ?
C8 C9 C10 C1 -83.63(16) . . . . ?
C8 C9 C10 C14 74.78(17) . . . . ?
C8 C7 C11 C13 2.52(17) . . . . ?
C6 C7 C11 C13 -108.37(11) . . . . ?
C8 C7 C11 C12 -141.99(13) . . . . ?
C6 C7 C11 C12 107.12(12) . . . . ?
C8 C7 C11 C6 110.89(13) . . . . ?
C5 C6 C11 C7 -113.34(12) . . . . ?
C5 C6 C11 C13 -2.09(16) . . . . ?
C7 C6 C11 C13 111.25(12) . . . . ?
C5 C6 C11 C12 140.15(12) . . . . ?
C7 C6 C11 C12 -106.51(12) . . . . ?
C5 C4 C1' C2' 47.12(15) . . . . ?
C3 C4 C1' C2' -132.13(10) . . . . ?
C5 C4 C1' C10' -78.39(13) . . . . ?
C3 C4 C1' C10' 102.37(11) . . . . ?
C4 C1' C2' C3' -177.90(9) . . . . ?
C10' C1' C2' C3' -51.96(13) . . . . ?
C1' C2' C3' C4' 49.84(13) . . . . ?
C2' C3' C4' O2 122.58(11) . . . . ?
C2' C3' C4' C5' -54.33(12) . . . . ?
O2 C4' C5' C6' 116.09(11) . . . . ?
C3' C4' C5' C6' -66.97(11) . . . . ?
O2 C4' C5' C10' -118.65(11) . . . . ?
C3' C4' C5' C10' 58.29(12) . . . . ?
C4' C5' C6' C11' -136.30(10) . . . . ?
C10' C5' C6' C11' 101.41(11) . . . . ?
C4' C5' C6' C7' 152.46(10) . . . . ?
C10' C5' C6' C7' 30.17(14) . . . . ?
C5' C6' C7' C11' 112.98(11) . . . . ?
C11' C6' C7' C8' -114.02(11) . . . . ?
C5' C6' C7' C8' -1.04(15) . . . . ?
C11' C7' C8' C9' -71.18(13) . . . . ?
C6' C7' C8' C9' 0.56(15) . . . . ?
C7' C8' C9' C10' -30.45(13) . . . . ?
C8' C9' C10' C14' 171.97(9) . . . . ?
C8' C9' C10' C1' -63.71(12) . . . . ?
C8' C9' C10' C5' 57.23(11) . . . . ?
C4 C1' C10' C14' 62.37(11) . . . . ?
C2' C1' C10' C14' -63.57(11) . . . . ?
C4 C1' C10' C9' -59.70(11) . . . . ?
C2' C1' C10' C9' 174.36(9) . . . . ?
C4 C1' C10' C5' -178.76(8) . . . . ?
C2' C1' C10' C5' 55.30(11) . . . . ?
C4' C5' C10' C14' 65.07(11) . . . . ?
C6' C5' C10' C14' -171.46(9) . . . . ?
C4' C5' C10' C9' -179.48(8) . . . . ?
C6' C5' C10' C9' -56.02(11) . . . . ?
C4' C5' C10' C1' -56.87(11) . . . . ?
C6' C5' C10' C1' 66.59(11) . . . . ?
C7' C6' C11' C13' -107.77(10) . . . . ?
C5' C6' C11' C13' 144.69(10) . . . . ?
C7' C6' C11' C12' 107.90(11) . . . . ?
C5' C6' C11' C12' 0.35(15) . . . . ?
C5' C6' C11' C7' -107.55(11) . . . . ?
C8' C7' C11' C6' 107.63(11) . . . . ?
C8' C7' C11' C13' -146.88(10) . . . . ?
C6' C7' C11' C13' 105.48(11) . . . . ?
C8' C7' C11' C12' -4.42(15) . . . . ?
C6' C7' C11' C12' -112.06(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        69.65
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# 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_dm11625_0m
_database_code_depnum_ccdc_archive 'CCDC 931555'
_audit_update_record             
;
2013-03-28 deposited with the CCDC.
2014-12-08 downloaded from the CCDC.
;
#TrackingRef 'cu_dm11625_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H48 O6'
_chemical_formula_weight         504.68

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   9.0356(2)
_cell_length_b                   14.7212(4)
_cell_length_c                   20.2608(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2694.99(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9778
_cell_measurement_theta_min      3.71
_cell_measurement_theta_max      66.17

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8880
_exptl_absorpt_correction_T_max  0.9054
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51177
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.71
_diffrn_reflns_theta_max         66.61
_reflns_number_total             4760
_reflns_number_gt                4670
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0464P)²+0.4455P] 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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4760
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
O1 O 0.91950(11) 0.63577(6) 0.11714(4) 0.0254(2) Uani 1 1 d . . .
H1 H 0.8354 0.6413 0.0999 0.038 Uiso 1 1 calc R . .
O2 O 1.02362(10) 0.74054(6) 0.36533(4) 0.0226(2) Uani 1 1 d . . .
H2 H 1.0181 0.7913 0.3841 0.034 Uiso 1 1 calc R . .
O3 O 0.71759(9) 0.49767(6) 0.11076(4) 0.01864(19) Uani 1 1 d . . .
O4 O 0.95222(9) 0.44292(6) 0.09778(4) 0.01934(19) Uani 1 1 d . . .
O5 O 0.93393(10) 0.38205(6) -0.00647(4) 0.0225(2) Uani 1 1 d . . .
H5 H 1.0242 0.3885 -0.0153 0.034 Uiso 1 1 calc R . .
O6 O 0.23774(10) 0.38966(7) -0.04371(5) 0.0281(2) Uani 1 1 d . . .
H6 H 0.2775 0.3551 -0.0715 0.042 Uiso 1 1 calc R . .
C1 C 1.08389(14) 0.64591(9) 0.24428(6) 0.0225(3) Uani 1 1 d . . .
H1A H 1.0960 0.7030 0.2190 0.027 Uiso 1 1 calc R . .
H1B H 1.1686 0.6386 0.2748 0.027 Uiso 1 1 calc R . .
C2 C 1.06844(14) 0.56426(9) 0.19848(7) 0.0237(3) Uani 1 1 d . . .
H2A H 1.0808 0.5067 0.2231 0.028 Uiso 1 1 calc R . .
H2B H 1.1425 0.5667 0.1625 0.028 Uiso 1 1 calc R . .
C3 C 0.91137(14) 0.57272(8) 0.17109(6) 0.0181(2) Uani 1 1 d . . .
C4 C 0.81974(13) 0.61507(8) 0.22895(6) 0.0163(2) Uani 1 1 d . . .
H4 H 0.7716 0.6716 0.2119 0.020 Uiso 1 1 calc R . .
C5 C 0.70034(13) 0.55677(8) 0.25932(6) 0.0172(2) Uani 1 1 d . . .
H5A H 0.7322 0.4938 0.2711 0.021 Uiso 1 1 calc R . .
C6 C 0.59519(14) 0.60067(9) 0.30845(6) 0.0202(3) Uani 1 1 d . . .
H6A H 0.5692 0.5608 0.3467 0.024 Uiso 1 1 calc R . .
C7 C 0.61250(14) 0.70007(9) 0.32650(6) 0.0228(3) Uani 1 1 d . . .
H7A H 0.5286 0.7187 0.3548 0.027 Uiso 1 1 calc R . .
H7B H 0.6090 0.7372 0.2858 0.027 Uiso 1 1 calc R . .
C8 C 0.75876(15) 0.71902(9) 0.36306(6) 0.0216(3) Uani 1 1 d . . .
H8A H 0.7460 0.7753 0.3892 0.026 Uiso 1 1 calc R . .
H8B H 0.7758 0.6688 0.3947 0.026 Uiso 1 1 calc R . .
C9 C 0.89895(14) 0.72973(8) 0.32076(6) 0.0195(3) Uani 1 1 d . . .
C10 C 0.93628(13) 0.64399(8) 0.28136(6) 0.0168(2) Uani 1 1 d . . .
H10 H 0.9428 0.5931 0.3140 0.020 Uiso 1 1 calc R . .
C11 C 0.53739(13) 0.56631(9) 0.24257(6) 0.0202(3) Uani 1 1 d . . .
C12 C 0.48624(14) 0.63184(10) 0.18995(6) 0.0245(3) Uani 1 1 d . . .
H12A H 0.5478 0.6866 0.1912 0.037 Uiso 1 1 calc R . .
H12B H 0.3827 0.6483 0.1980 0.037 Uiso 1 1 calc R . .
H12C H 0.4951 0.6031 0.1465 0.037 Uiso 1 1 calc R . .
C13 C 0.44752(15) 0.47920(10) 0.24363(7) 0.0276(3) Uani 1 1 d . . .
H13A H 0.3442 0.4933 0.2543 0.041 Uiso 1 1 calc R . .
H13B H 0.4879 0.4380 0.2771 0.041 Uiso 1 1 calc R . .
H13C H 0.4524 0.4500 0.2002 0.041 Uiso 1 1 calc R . .
C14 C 0.88764(17) 0.81482(9) 0.27805(7) 0.0258(3) Uani 1 1 d . . .
H14D H 0.8684 0.8677 0.3062 0.039 Uiso 1 1 calc R . .
H14E H 0.8065 0.8077 0.2464 0.039 Uiso 1 1 calc R . .
H14F H 0.9808 0.8238 0.2541 0.039 Uiso 1 1 calc R . .
C15 C 0.85319(13) 0.48216(9) 0.14450(6) 0.0174(2) Uani 1 1 d . . .
H15 H 0.8368 0.4389 0.1819 0.021 Uiso 1 1 calc R . .
C1' C 0.49577(14) 0.36106(9) 0.04283(6) 0.0198(3) Uani 1 1 d . . .
H1'1 H 0.4433 0.3855 0.0819 0.024 Uiso 1 1 calc R . .
H1'2 H 0.4517 0.3018 0.0306 0.024 Uiso 1 1 calc R . .
C2' C 0.66167(14) 0.35209(9) 0.05598(6) 0.0197(3) Uani 1 1 d . . .
H2'1 H 0.7085 0.3108 0.0236 0.024 Uiso 1 1 calc R . .
H2'2 H 0.6802 0.3286 0.1010 0.024 Uiso 1 1 calc R . .
C3' C 0.72109(13) 0.44901(8) 0.04854(6) 0.0165(2) Uani 1 1 d . . .
C4' C 0.61067(13) 0.49896(8) 0.00207(5) 0.0162(2) Uani 1 1 d . . .
H4' H 0.5625 0.5485 0.0281 0.019 Uiso 1 1 calc R . .
C5' C 0.68011(14) 0.54186(9) -0.05839(6) 0.0197(3) Uani 1 1 d . . .
H5' H 0.7529 0.5021 -0.0818 0.024 Uiso 1 1 calc R . .
C6' C 0.58475(16) 0.59929(9) -0.10367(6) 0.0242(3) Uani 1 1 d . . .
H6' H 0.6063 0.5906 -0.1517 0.029 Uiso 1 1 calc R . .
C7' C 0.42302(16) 0.61466(9) -0.08845(7) 0.0265(3) Uani 1 1 d . . .
H7'1 H 0.3823 0.6591 -0.1203 0.032 Uiso 1 1 calc R . .
H7'2 H 0.4140 0.6411 -0.0437 0.032 Uiso 1 1 calc R . .
C8' C 0.33106(15) 0.52732(10) -0.09173(7) 0.0259(3) Uani 1 1 d . . .
H8'1 H 0.3656 0.4913 -0.1300 0.031 Uiso 1 1 calc R . .
H8'2 H 0.2268 0.5442 -0.1003 0.031 Uiso 1 1 calc R . .
C9' C 0.33528(14) 0.46635(9) -0.03045(6) 0.0214(3) Uani 1 1 d . . .
C10' C 0.49011(13) 0.42798(8) -0.01508(6) 0.0173(2) Uani 1 1 d . . .
H10' H 0.5244 0.3946 -0.0553 0.021 Uiso 1 1 calc R . .
C11' C 0.70943(17) 0.64302(9) -0.06561(7) 0.0276(3) Uani 1 1 d . . .
C12' C 0.6750(2) 0.70979(10) -0.01107(8) 0.0358(3) Uani 1 1 d . . .
H12D H 0.6422 0.7674 -0.0304 0.054 Uiso 1 1 calc R . .
H12E H 0.7640 0.7201 0.0155 0.054 Uiso 1 1 calc R . .
H12F H 0.5963 0.6852 0.0170 0.054 Uiso 1 1 calc R . .
C13' C 0.8466(2) 0.66841(12) -0.10445(9) 0.0438(4) Uani 1 1 d . . .
H13D H 0.8612 0.6246 -0.1403 0.066 Uiso 1 1 calc R . .
H13E H 0.9329 0.6676 -0.0752 0.066 Uiso 1 1 calc R . .
H13F H 0.8344 0.7294 -0.1230 0.066 Uiso 1 1 calc R . .
C14' C 0.26389(15) 0.51444(10) 0.02821(7) 0.0263(3) Uani 1 1 d . . .
H14A H 0.1714 0.5432 0.0141 0.039 Uiso 1 1 calc R . .
H14B H 0.3316 0.5609 0.0452 0.039 Uiso 1 1 calc R . .
H14C H 0.2429 0.4701 0.0630 0.039 Uiso 1 1 calc R . .
C15' C 0.88727(14) 0.45304(8) 0.03321(6) 0.0170(2) Uani 1 1 d . . .
H15' H 0.9145 0.5129 0.0133 0.020 Uiso 1 1 calc R . .


_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 C3 1.4359(15) . ?
O1 H1 0.8400 . ?
O2 C9 1.4524(15) . ?
O2 H2 0.8400 . ?
O3 C15 1.4215(14) . ?
O3 C3' 1.4502(14) . ?
O4 C15 1.4248(14) . ?
O4 C15' 1.4416(14) . ?
O5 C15' 1.3842(15) . ?
O5 H5 0.8400 . ?
O6 C9' 1.4571(16) . ?
O6 H6 0.8400 . ?
C1 C2 1.5249(17) . ?
C1 C10 1.5311(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.5290(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C15 1.5310(17) . ?
C3 C4 1.5648(16) . ?
C4 C5 1.5096(17) . ?
C4 C10 1.5549(16) . ?
C4 H4 1.0000 . ?
C5 C11 1.5174(17) . ?
C5 C6 1.5204(17) . ?
C5 H5A 1.0000 . ?
C6 C7 1.5163(18) . ?
C6 C11 1.5200(17) . ?
C6 H6A 1.0000 . ?
C7 C8 1.5405(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5376(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.5259(18) . ?
C9 C10 1.5310(16) . ?
C10 H10 1.0000 . ?
C11 C12 1.5103(18) . ?
C11 C13 1.5181(18) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14D 0.9800 . ?
C14 H14E 0.9800 . ?
C14 H14F 0.9800 . ?
C15 H15 1.0000 . ?
C1' C2' 1.5283(17) . ?
C1' C10' 1.5329(17) . ?
C1' H1'1 0.9900 . ?
C1' H1'2 0.9900 . ?
C2' C3' 1.5318(17) . ?
C2' H2'1 0.9900 . ?
C2' H2'2 0.9900 . ?
C3' C15' 1.5345(17) . ?
C3' C4' 1.5566(16) . ?
C4' C5' 1.5142(16) . ?
C4' C10' 1.5489(16) . ?
C4' H4' 1.0000 . ?
C5' C6' 1.5162(18) . ?
C5' C11' 1.5196(18) . ?
C5' H5' 1.0000 . ?
C6' C11' 1.509(2) . ?
C6' C7' 1.5105(19) . ?
C6' H6' 1.0000 . ?
C7' C8' 1.532(2) . ?
C7' H7'1 0.9900 . ?
C7' H7'2 0.9900 . ?
C8' C9' 1.5325(19) . ?
C8' H8'1 0.9900 . ?
C8' H8'2 0.9900 . ?
C9' C14' 1.5265(18) . ?
C9' C10' 1.5405(17) . ?
C10' H10' 1.0000 . ?
C11' C12' 1.512(2) . ?
C11' C13' 1.515(2) . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 0.9800 . ?
C13' H13D 0.9800 . ?
C13' H13E 0.9800 . ?
C13' H13F 0.9800 . ?
C14' H14A 0.9800 . ?
C14' H14B 0.9800 . ?
C14' H14C 0.9800 . ?
C15' H15' 1.0000 . ?

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 O1 H1 109.5 . . ?
C9 O2 H2 109.5 . . ?
C15 O3 C3' 108.66(8) . . ?
C15 O4 C15' 107.78(9) . . ?
C15' O5 H5 109.5 . . ?
C9' O6 H6 109.5 . . ?
C2 C1 C10 101.79(10) . . ?
C2 C1 H1A 111.4 . . ?
C10 C1 H1A 111.4 . . ?
C2 C1 H1B 111.4 . . ?
C10 C1 H1B 111.4 . . ?
H1A C1 H1B 109.3 . . ?
C1 C2 C3 103.98(10) . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
O1 C3 C2 106.34(10) . . ?
O1 C3 C15 108.22(10) . . ?
C2 C3 C15 112.06(10) . . ?
O1 C3 C4 109.87(9) . . ?
C2 C3 C4 104.58(9) . . ?
C15 C3 C4 115.40(10) . . ?
C5 C4 C10 111.18(10) . . ?
C5 C4 C3 117.19(10) . . ?
C10 C4 C3 105.22(9) . . ?
C5 C4 H4 107.6 . . ?
C10 C4 H4 107.6 . . ?
C3 C4 H4 107.6 . . ?
C4 C5 C11 123.34(10) . . ?
C4 C5 C6 118.15(11) . . ?
C11 C5 C6 60.05(8) . . ?
C4 C5 H5A 114.7 . . ?
C11 C5 H5A 114.7 . . ?
C6 C5 H5A 114.7 . . ?
C7 C6 C11 124.64(11) . . ?
C7 C6 C5 120.24(11) . . ?
C11 C6 C5 59.88(8) . . ?
C7 C6 H6A 113.8 . . ?
C11 C6 H6A 113.8 . . ?
C5 C6 H6A 113.8 . . ?
C6 C7 C8 112.29(11) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 117.21(10) . . ?
C9 C8 H8A 108.0 . . ?
C7 C8 H8A 108.0 . . ?
C9 C8 H8B 108.0 . . ?
C7 C8 H8B 108.0 . . ?
H8A C8 H8B 107.2 . . ?
O2 C9 C14 108.34(10) . . ?
O2 C9 C10 104.10(9) . . ?
C14 C9 C10 113.32(10) . . ?
O2 C9 C8 107.68(9) . . ?
C14 C9 C8 110.19(11) . . ?
C10 C9 C8 112.80(10) . . ?
C9 C10 C1 115.63(10) . . ?
C9 C10 C4 115.63(10) . . ?
C1 C10 C4 105.06(9) . . ?
C9 C10 H10 106.6 . . ?
C1 C10 H10 106.6 . . ?
C4 C10 H10 106.6 . . ?
C12 C11 C5 120.92(11) . . ?
C12 C11 C13 112.70(11) . . ?
C5 C11 C13 115.96(11) . . ?
C12 C11 C6 120.83(11) . . ?
C5 C11 C6 60.07(8) . . ?
C13 C11 C6 116.90(11) . . ?
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 . . ?
C9 C14 H14D 109.5 . . ?
C9 C14 H14E 109.5 . . ?
H14D C14 H14E 109.5 . . ?
C9 C14 H14F 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
O3 C15 O4 106.67(9) . . ?
O3 C15 C3 108.99(10) . . ?
O4 C15 C3 111.78(10) . . ?
O3 C15 H15 109.8 . . ?
O4 C15 H15 109.8 . . ?
C3 C15 H15 109.8 . . ?
C2' C1' C10' 102.81(10) . . ?
C2' C1' H1'1 111.2 . . ?
C10' C1' H1'1 111.2 . . ?
C2' C1' H1'2 111.2 . . ?
C10' C1' H1'2 111.2 . . ?
H1'1 C1' H1'2 109.1 . . ?
C1' C2' C3' 104.25(10) . . ?
C1' C2' H2'1 110.9 . . ?
C3' C2' H2'1 110.9 . . ?
C1' C2' H2'2 110.9 . . ?
C3' C2' H2'2 110.9 . . ?
H2'1 C2' H2'2 108.9 . . ?
O3 C3' C2' 111.53(9) . . ?
O3 C3' C15' 100.27(9) . . ?
C2' C3' C15' 113.51(10) . . ?
O3 C3' C4' 106.17(9) . . ?
C2' C3' C4' 105.96(10) . . ?
C15' C3' C4' 119.11(10) . . ?
C5' C4' C10' 113.03(10) . . ?
C5' C4' C3' 114.88(10) . . ?
C10' C4' C3' 105.53(9) . . ?
C5' C4' H4' 107.7 . . ?
C10' C4' H4' 107.7 . . ?
C3' C4' H4' 107.7 . . ?
C4' C5' C6' 119.11(11) . . ?
C4' C5' C11' 123.97(11) . . ?
C6' C5' C11' 59.62(9) . . ?
C4' C5' H5' 114.4 . . ?
C6' C5' H5' 114.4 . . ?
C11' C5' H5' 114.4 . . ?
C11' C6' C7' 123.64(12) . . ?
C11' C6' C5' 60.30(8) . . ?
C7' C6' C5' 120.65(11) . . ?
C11' C6' H6' 114.0 . . ?
C7' C6' H6' 114.0 . . ?
C5' C6' H6' 114.0 . . ?
C6' C7' C8' 112.96(11) . . ?
C6' C7' H7'1 109.0 . . ?
C8' C7' H7'1 109.0 . . ?
C6' C7' H7'2 109.0 . . ?
C8' C7' H7'2 109.0 . . ?
H7'1 C7' H7'2 107.8 . . ?
C7' C8' C9' 116.29(11) . . ?
C7' C8' H8'1 108.2 . . ?
C9' C8' H8'1 108.2 . . ?
C7' C8' H8'2 108.2 . . ?
C9' C8' H8'2 108.2 . . ?
H8'1 C8' H8'2 107.4 . . ?
O6 C9' C14' 104.31(10) . . ?
O6 C9' C8' 106.82(10) . . ?
C14' C9' C8' 110.40(11) . . ?
O6 C9' C10' 107.61(10) . . ?
C14' C9' C10' 113.35(11) . . ?
C8' C9' C10' 113.65(10) . . ?
C1' C10' C9' 114.88(10) . . ?
C1' C10' C4' 103.80(9) . . ?
C9' C10' C4' 115.89(10) . . ?
C1' C10' H10' 107.3 . . ?
C9' C10' H10' 107.3 . . ?
C4' C10' H10' 107.3 . . ?
C6' C11' C12' 119.81(13) . . ?
C6' C11' C13' 116.78(13) . . ?
C12' C11' C13' 112.82(13) . . ?
C6' C11' C5' 60.08(9) . . ?
C12' C11' C5' 122.07(12) . . ?
C13' C11' C5' 115.75(13) . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C11' C13' H13D 109.5 . . ?
C11' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C11' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C9' C14' H14A 109.5 . . ?
C9' C14' H14B 109.5 . . ?
H14A C14' H14B 109.5 . . ?
C9' C14' H14C 109.5 . . ?
H14A C14' H14C 109.5 . . ?
H14B C14' H14C 109.5 . . ?
O5 C15' O4 108.98(10) . . ?
O5 C15' C3' 112.73(10) . . ?
O4 C15' C3' 102.16(9) . . ?
O5 C15' H15' 110.9 . . ?
O4 C15' H15' 110.9 . . ?
C3' C15' H15' 110.9 . . ?

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
C10 C1 C2 C3 44.42(12) . . . . ?
C1 C2 C3 O1 82.66(12) . . . . ?
C1 C2 C3 C15 -159.28(10) . . . . ?
C1 C2 C3 C4 -33.58(12) . . . . ?
O1 C3 C4 C5 131.93(11) . . . . ?
C2 C3 C4 C5 -114.29(11) . . . . ?
C15 C3 C4 C5 9.28(15) . . . . ?
O1 C3 C4 C10 -103.97(11) . . . . ?
C2 C3 C4 C10 9.81(12) . . . . ?
C15 C3 C4 C10 133.38(11) . . . . ?
C10 C4 C5 C11 138.77(11) . . . . ?
C3 C4 C5 C11 -100.20(14) . . . . ?
C10 C4 C5 C6 67.79(13) . . . . ?
C3 C4 C5 C6 -171.19(10) . . . . ?
C4 C5 C6 C7 -0.71(16) . . . . ?
C11 C5 C6 C7 -114.98(13) . . . . ?
C4 C5 C6 C11 114.28(12) . . . . ?
C11 C6 C7 C8 -137.55(12) . . . . ?
C5 C6 C7 C8 -65.21(15) . . . . ?
C6 C7 C8 C9 81.34(14) . . . . ?
C7 C8 C9 O2 -176.02(10) . . . . ?
C7 C8 C9 C14 66.01(14) . . . . ?
C7 C8 C9 C10 -61.73(14) . . . . ?
O2 C9 C10 C1 -56.87(13) . . . . ?
C14 C9 C10 C1 60.61(14) . . . . ?
C8 C9 C10 C1 -173.31(10) . . . . ?
O2 C9 C10 C4 179.77(9) . . . . ?
C14 C9 C10 C4 -62.74(14) . . . . ?
C8 C9 C10 C4 63.34(13) . . . . ?
C2 C1 C10 C9 -166.59(10) . . . . ?
C2 C1 C10 C4 -37.84(12) . . . . ?
C5 C4 C10 C9 -86.08(13) . . . . ?
C3 C4 C10 C9 146.10(10) . . . . ?
C5 C4 C10 C1 145.17(10) . . . . ?
C3 C4 C10 C1 17.35(12) . . . . ?
C4 C5 C11 C12 4.33(19) . . . . ?
C6 C5 C11 C12 110.15(14) . . . . ?
C4 C5 C11 C13 146.70(12) . . . . ?
C6 C5 C11 C13 -107.48(12) . . . . ?
C4 C5 C11 C6 -105.82(13) . . . . ?
C7 C6 C11 C12 -2.43(18) . . . . ?
C5 C6 C11 C12 -110.30(13) . . . . ?
C7 C6 C11 C5 107.87(13) . . . . ?
C7 C6 C11 C13 -146.21(12) . . . . ?
C5 C6 C11 C13 105.92(12) . . . . ?
C3' O3 C15 O4 13.34(12) . . . . ?
C3' O3 C15 C3 134.19(10) . . . . ?
C15' O4 C15 O3 12.22(12) . . . . ?
C15' O4 C15 C3 -106.82(11) . . . . ?
O1 C3 C15 O3 -54.03(12) . . . . ?
C2 C3 C15 O3 -170.97(9) . . . . ?
C4 C3 C15 O3 69.49(12) . . . . ?
O1 C3 C15 O4 63.63(12) . . . . ?
C2 C3 C15 O4 -53.31(13) . . . . ?
C4 C3 C15 O4 -172.85(9) . . . . ?
C10' C1' C2' C3' 40.67(12) . . . . ?
C15 O3 C3' C2' 89.21(11) . . . . ?
C15 O3 C3' C15' -31.27(11) . . . . ?
C15 O3 C3' C4' -155.83(9) . . . . ?
C1' C2' C3' O3 89.82(11) . . . . ?
C1' C2' C3' C15' -157.81(10) . . . . ?
C1' C2' C3' C4' -25.27(12) . . . . ?
O3 C3' C4' C5' 116.52(11) . . . . ?
C2' C3' C4' C5' -124.78(11) . . . . ?
C15' C3' C4' C5' 4.57(15) . . . . ?
O3 C3' C4' C10' -118.27(10) . . . . ?
C2' C3' C4' C10' 0.43(12) . . . . ?
C15' C3' C4' C10' 129.78(11) . . . . ?
C10' C4' C5' C6' 64.23(15) . . . . ?
C3' C4' C5' C6' -174.58(11) . . . . ?
C10' C4' C5' C11' 135.41(13) . . . . ?
C3' C4' C5' C11' -103.40(14) . . . . ?
C4' C5' C6' C11' 114.52(13) . . . . ?
C4' C5' C6' C7' 0.73(18) . . . . ?
C11' C5' C6' C7' -113.79(14) . . . . ?
C11' C6' C7' C8' -137.89(12) . . . . ?
C5' C6' C7' C8' -65.19(16) . . . . ?
C6' C7' C8' C9' 81.70(14) . . . . ?
C7' C8' C9' O6 178.35(11) . . . . ?
C7' C8' C9' C14' 65.52(15) . . . . ?
C7' C8' C9' C10' -63.13(15) . . . . ?
C2' C1' C10' C9' -167.73(10) . . . . ?
C2' C1' C10' C4' -40.18(12) . . . . ?
O6 C9' C10' C1' -57.55(13) . . . . ?
C14' C9' C10' C1' 57.26(14) . . . . ?
C8' C9' C10' C1' -175.61(10) . . . . ?
O6 C9' C10' C4' -178.70(9) . . . . ?
C14' C9' C10' C4' -63.89(14) . . . . ?
C8' C9' C10' C4' 63.24(14) . . . . ?
C5' C4' C10' C1' 150.79(10) . . . . ?
C3' C4' C10' C1' 24.44(11) . . . . ?
C5' C4' C10' C9' -82.29(13) . . . . ?
C3' C4' C10' C9' 151.36(10) . . . . ?
C7' C6' C11' C12' -3.12(19) . . . . ?
C5' C6' C11' C12' -112.10(14) . . . . ?
C7' C6' C11' C13' -145.29(14) . . . . ?
C5' C6' C11' C13' 105.72(14) . . . . ?
C7' C6' C11' C5' 108.99(14) . . . . ?
C4' C5' C11' C6' -106.56(13) . . . . ?
C4' C5' C11' C12' 1.9(2) . . . . ?
C6' C5' C11' C12' 108.44(16) . . . . ?
C4' C5' C11' C13' 146.01(13) . . . . ?
C6' C5' C11' C13' -107.43(14) . . . . ?
C15 O4 C15' O5 -150.51(10) . . . . ?
C15 O4 C15' C3' -31.03(12) . . . . ?
O3 C3' C15' O5 153.98(9) . . . . ?
C2' C3' C15' O5 34.93(14) . . . . ?
C4' C3' C15' O5 -90.89(13) . . . . ?
O3 C3' C15' O4 37.17(11) . . . . ?
C2' C3' C15' O4 -81.87(11) . . . . ?
C4' C3' C15' O4 152.30(10) . . . . ?

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
O2 H2 O4 0.84 2.28 3.0793(12) 159.6 3_755
O5 H5 O6 0.84 2.01 2.8491(13) 172.6 1_655
O6 H6 O2 0.84 2.62 3.4236(13) 161.4 4_664

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        66.61
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032


