# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       hans-joachim.knoelker@tu-dresden.de
_publ_contact_author_name        'Hans-Joachim Knolker'
loop_
_publ_author_name
Kataeva
'Arndt W. Schmidt'
'Teymuras V. Kurzchalia'
'Hans-Joachim Knolker'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 867379'
#TrackingRef 'kno19.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H46 O2'
_chemical_formula_sum            'C27 H46 O2'
_chemical_formula_weight         402.64

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   11.0257(6)
_cell_length_b                   7.5583(4)
_cell_length_c                   14.7907(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.487(4)
_cell_angle_gamma                90.00
_cell_volume                     1226.94(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    198(2)
_cell_measurement_reflns_used    945
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      22.93

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_process_details   
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)'

_exptl_special_details           
;
?
;

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_device       'Bruker Kappa APEX II CCD'
_diffrn_ambient_temperature      198(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       '0.5 deg frames in phi and omega'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27556
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         29.48
_reflns_number_total             6718
_reflns_number_gt                3560
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)'
_computing_cell_refinement       'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)'
_computing_data_reduction        'SAINT NT v6.0 (Bruker AXS, 2003)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'WinGX (Farrugia 1999), enCIFer (Allen et al. 2'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0436P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(12)
_refine_ls_number_reflns         6718
_refine_ls_number_parameters     274
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_restrained_S_all      0.829
_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 0.66697(18) -0.09144(19) 0.69245(12) 0.0471(5) Uani 1 1 d . . .
H1A H 0.6429 -0.1923 0.6519 0.057 Uiso 1 1 calc R . .
H1B H 0.7530 -0.1094 0.7165 0.057 Uiso 1 1 calc R . .
C2 C 0.58809(17) -0.0916(2) 0.77109(12) 0.0497(5) Uani 1 1 d . . .
H2A H 0.5012 -0.0822 0.7475 0.060 Uiso 1 1 calc R . .
H2B H 0.5994 -0.2043 0.8050 0.060 Uiso 1 1 calc R . .
C3 C 0.62173(16) 0.0610(2) 0.83385(11) 0.0462(4) Uani 1 1 d . . .
H3A H 0.7097 0.0504 0.8568 0.055 Uiso 1 1 calc R . .
O3 O 0.55068(13) 0.06248(19) 0.90982(9) 0.0672(4) Uani 1 1 d . . .
H3 H 0.572(2) -0.039(3) 0.9403(15) 0.097(8) Uiso 1 1 d . . .
C4 C 0.60307(17) 0.2324(2) 0.78245(12) 0.0495(5) Uani 1 1 d . . .
H4A H 0.6256 0.3327 0.8237 0.059 Uiso 1 1 calc R . .
H4B H 0.5160 0.2451 0.7601 0.059 Uiso 1 1 calc R . .
C5 C 0.68034(15) 0.23754(19) 0.70233(11) 0.0384(4) Uani 1 1 d . . .
H5A H 0.7671 0.2281 0.7285 0.046 Uiso 1 1 calc R . .
C6 C 0.66954(16) 0.41097(19) 0.65084(12) 0.0446(4) Uani 1 1 d . . .
H6A H 0.6870 0.5097 0.6941 0.054 Uiso 1 1 calc R . .
H6B H 0.5848 0.4249 0.6231 0.054 Uiso 1 1 calc R . .
C7 C 0.75576(15) 0.42245(19) 0.57688(11) 0.0417(4) Uani 1 1 d . . .
H7A H 0.7301 0.5225 0.5363 0.050 Uiso 1 1 calc R . .
H7B H 0.8385 0.4494 0.6056 0.050 Uiso 1 1 calc R . .
C8 C 0.76221(13) 0.2579(2) 0.51999(11) 0.0374(4) Uani 1 1 d . . .
C9 C 0.75891(15) 0.0843(2) 0.57167(11) 0.0422(4) Uani 1 1 d . . .
H9A H 0.8374 0.0785 0.6115 0.051 Uiso 1 1 calc R . .
C10 C 0.65737(13) 0.0805(2) 0.63647(10) 0.0374(4) Uani 1 1 d . . .
C11 C 0.7593(2) -0.0748(2) 0.50893(14) 0.0683(6) Uani 1 1 d . . .
H11A H 0.7856 -0.1805 0.5452 0.082 Uiso 1 1 calc R . .
H11B H 0.6752 -0.0963 0.4813 0.082 Uiso 1 1 calc R . .
C12 C 0.8422(2) -0.0512(2) 0.43413(13) 0.0611(5) Uani 1 1 d . . .
H12A H 0.8404 -0.1598 0.3967 0.073 Uiso 1 1 calc R . .
H12B H 0.9269 -0.0333 0.4614 0.073 Uiso 1 1 calc R . .
C13 C 0.80376(15) 0.1069(2) 0.37348(11) 0.0418(4) Uani 1 1 d . . .
C14 C 0.78488(13) 0.2646(2) 0.43344(11) 0.0391(4) Uani 1 1 d . . .
C15 C 0.81154(16) 0.4314(2) 0.38210(12) 0.0474(5) Uani 1 1 d . . .
H15A H 0.8678 0.5094 0.4200 0.057 Uiso 1 1 calc R . .
H15B H 0.7354 0.4973 0.3642 0.057 Uiso 1 1 calc R . .
C16 C 0.87026(18) 0.3689(2) 0.29833(13) 0.0526(5) Uani 1 1 d . . .
H16A H 0.9439 0.4397 0.2900 0.063 Uiso 1 1 calc R . .
H16B H 0.8124 0.3810 0.2432 0.063 Uiso 1 1 calc R . .
C17 C 0.90406(15) 0.1738(2) 0.31536(12) 0.0403(4) Uani 1 1 d . . .
H17A H 0.9826 0.1720 0.3552 0.048 Uiso 1 1 calc R . .
C18 C 0.68539(15) 0.0679(3) 0.31363(13) 0.0641(5) Uani 1 1 d . . .
H18A H 0.6190 0.0490 0.3522 0.096 Uiso 1 1 calc R . .
H18B H 0.6960 -0.0387 0.2775 0.096 Uiso 1 1 calc R . .
H18C H 0.6655 0.1683 0.2730 0.096 Uiso 1 1 calc R . .
C19A C 0.53119(15) 0.0926(3) 0.58319(12) 0.0558(5) Uani 1 1 d . . .
H19A H 0.5064 -0.0248 0.5602 0.084 Uiso 1 1 calc R . .
H19B H 0.5346 0.1744 0.5321 0.084 Uiso 1 1 calc R . .
H19C H 0.4719 0.1359 0.6233 0.084 Uiso 1 1 calc R . .
C20 C 0.92611(14) 0.0745(2) 0.22771(11) 0.0447(4) Uani 1 1 d . . .
H20A H 0.8516 0.0892 0.1842 0.054 Uiso 1 1 calc R . .
C21 C 0.94716(16) -0.1245(2) 0.24210(13) 0.0533(5) Uani 1 1 d . . .
H21A H 0.9742 -0.1767 0.1868 0.080 Uiso 1 1 calc R . .
H21B H 0.8710 -0.1808 0.2558 0.080 Uiso 1 1 calc R . .
H21C H 1.0097 -0.1431 0.2929 0.080 Uiso 1 1 calc R . .
C22 C 1.03280(17) 0.1581(3) 0.18445(13) 0.0566(5) Uani 1 1 d . . .
H22A H 1.0162 0.2862 0.1769 0.068 Uiso 1 1 calc R . .
H22B H 1.1067 0.1456 0.2276 0.068 Uiso 1 1 calc R . .
C23 C 1.06121(17) 0.0848(3) 0.09352(13) 0.0616(5) Uani 1 1 d . . .
H23A H 0.9873 0.0921 0.0500 0.074 Uiso 1 1 calc R . .
H23B H 1.0839 -0.0415 0.1007 0.074 Uiso 1 1 calc R . .
C24 C 1.16466(18) 0.1851(3) 0.05525(13) 0.0604(5) Uani 1 1 d . . .
H24A H 1.1398 0.3104 0.0470 0.072 Uiso 1 1 calc R . .
H24B H 1.2364 0.1822 0.1009 0.072 Uiso 1 1 calc R . .
C25 C 1.20337(18) 0.1172(3) -0.03422(12) 0.0570(5) Uani 1 1 d . . .
H25A H 1.1283 0.1076 -0.0776 0.068 Uiso 1 1 calc R . .
C26 C 1.28677(18) 0.2490(3) -0.07328(13) 0.0643(5) Uani 1 1 d . . .
H26A H 1.3072 0.2063 -0.1333 0.077 Uiso 1 1 calc R . .
H26B H 1.2436 0.3633 -0.0827 0.077 Uiso 1 1 calc R . .
O26 O 1.39657(13) 0.2760(2) -0.01579(9) 0.0600(4) Uani 1 1 d . . .
H26 H 1.453(2) 0.209(3) -0.0387(16) 0.105(10) Uiso 1 1 d . . .
C27 C 1.26042(19) -0.0642(3) -0.02565(14) 0.0665(6) Uani 1 1 d . . .
H27A H 1.2005 -0.1494 -0.0072 0.100 Uiso 1 1 calc R . .
H27B H 1.3308 -0.0613 0.0201 0.100 Uiso 1 1 calc R . .
H27C H 1.2871 -0.0999 -0.0843 0.100 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0673(12) 0.0263(9) 0.0493(10) 0.0040(8) 0.0139(10) -0.0027(8)
C2 0.0563(12) 0.0355(10) 0.0579(12) 0.0079(8) 0.0095(10) -0.0055(8)
C3 0.0515(10) 0.0397(9) 0.0494(10) 0.0060(9) 0.0159(9) 0.0026(9)
O3 0.0869(10) 0.0508(8) 0.0697(9) 0.0123(8) 0.0369(8) 0.0140(8)
C4 0.0595(11) 0.0356(10) 0.0542(12) -0.0020(8) 0.0096(10) 0.0032(8)
C5 0.0388(9) 0.0267(8) 0.0489(10) 0.0011(7) 0.0001(8) 0.0002(7)
C6 0.0558(11) 0.0248(9) 0.0531(10) -0.0026(8) 0.0051(9) 0.0009(7)
C7 0.0490(10) 0.0228(8) 0.0525(10) 0.0028(8) 0.0015(9) -0.0029(7)
C8 0.0377(9) 0.0225(7) 0.0519(10) 0.0028(8) 0.0026(8) -0.0025(8)
C9 0.0540(10) 0.0232(7) 0.0505(10) 0.0047(8) 0.0098(9) 0.0030(8)
C10 0.0426(9) 0.0226(7) 0.0462(9) 0.0012(8) 0.0006(8) -0.0034(8)
C11 0.1195(18) 0.0214(9) 0.0701(13) 0.0019(9) 0.0403(14) -0.0026(10)
C12 0.0977(16) 0.0266(9) 0.0627(12) 0.0042(9) 0.0270(12) 0.0115(10)
C13 0.0438(10) 0.0295(9) 0.0527(10) -0.0007(8) 0.0080(8) -0.0008(7)
C14 0.0385(9) 0.0255(7) 0.0536(11) 0.0049(8) 0.0060(8) 0.0011(8)
C15 0.0521(11) 0.0315(9) 0.0593(11) 0.0082(8) 0.0092(10) 0.0049(8)
C16 0.0610(12) 0.0383(10) 0.0604(12) 0.0073(9) 0.0156(10) -0.0010(9)
C17 0.0352(10) 0.0358(8) 0.0496(10) 0.0003(8) 0.0030(8) 0.0003(7)
C18 0.0456(11) 0.0695(13) 0.0786(13) -0.0220(12) 0.0139(10) -0.0175(11)
C19A 0.0515(11) 0.0528(11) 0.0606(11) 0.0048(10) -0.0084(9) -0.0145(9)
C20 0.0374(9) 0.0469(9) 0.0500(10) -0.0046(9) 0.0053(8) -0.0014(9)
C21 0.0489(11) 0.0497(10) 0.0611(12) -0.0150(9) 0.0043(10) 0.0030(9)
C22 0.0511(12) 0.0585(12) 0.0617(12) -0.0096(10) 0.0134(10) -0.0076(9)
C23 0.0554(12) 0.0713(12) 0.0595(12) -0.0083(11) 0.0128(10) -0.0071(11)
C24 0.0557(13) 0.0614(12) 0.0664(13) -0.0010(10) 0.0175(11) -0.0031(10)
C25 0.0501(12) 0.0718(14) 0.0482(11) 0.0041(10) 0.0003(9) -0.0008(10)
C26 0.0603(12) 0.0727(14) 0.0601(12) 0.0147(12) 0.0071(11) 0.0075(12)
O26 0.0557(9) 0.0617(8) 0.0644(8) -0.0134(7) 0.0148(7) -0.0010(7)
C27 0.0738(14) 0.0692(14) 0.0581(12) -0.0052(11) 0.0139(11) -0.0028(11)

_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 C2 1.517(2) . ?
C1 C10 1.539(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.505(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O3 1.430(2) . ?
C3 C4 1.506(2) . ?
C3 H3A 1.0000 . ?
O3 H3 0.91(2) . ?
C4 C5 1.525(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.515(2) . ?
C5 C10 1.541(2) . ?
C5 H5A 1.0000 . ?
C6 C7 1.519(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.507(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.329(2) . ?
C8 C9 1.521(2) . ?
C9 C11 1.519(2) . ?
C9 C10 1.542(2) . ?
C9 H9A 1.0000 . ?
C10 C19A 1.535(2) . ?
C11 C12 1.512(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.529(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.512(2) . ?
C13 C18 1.534(2) . ?
C13 C17 1.549(2) . ?
C14 C15 1.515(2) . ?
C15 C16 1.527(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.536(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C20 1.537(2) . ?
C17 H17A 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C20 C22 1.528(2) . ?
C20 C21 1.534(2) . ?
C20 H20A 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.515(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.523(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.518(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.507(3) . ?
C25 C27 1.509(3) . ?
C25 H25A 1.0000 . ?
C26 O26 1.426(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
O26 H26 0.89(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C2 C1 C10 113.45(13) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 110.29(14) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O3 C3 C2 111.68(14) . . ?
O3 C3 C4 109.36(15) . . ?
C2 C3 C4 109.53(13) . . ?
O3 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C3 O3 H3 104.5(15) . . ?
C3 C4 C5 110.78(14) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C4 112.94(13) . . ?
C6 C5 C10 110.38(12) . . ?
C4 C5 C10 113.67(12) . . ?
C6 C5 H5A 106.4 . . ?
C4 C5 H5A 106.4 . . ?
C10 C5 H5A 106.4 . . ?
C5 C6 C7 112.77(13) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 114.91(13) . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C14 C8 C7 121.97(15) . . ?
C14 C8 C9 122.22(14) . . ?
C7 C8 C9 115.27(13) . . ?
C11 C9 C8 111.99(13) . . ?
C11 C9 C10 114.18(14) . . ?
C8 C9 C10 112.44(13) . . ?
C11 C9 H9A 105.8 . . ?
C8 C9 H9A 105.8 . . ?
C10 C9 H9A 105.8 . . ?
C19A C10 C1 109.79(14) . . ?
C19A C10 C5 111.41(14) . . ?
C1 C10 C5 108.15(12) . . ?
C19A C10 C9 110.87(13) . . ?
C1 C10 C9 109.45(13) . . ?
C5 C10 C9 107.08(13) . . ?
C12 C11 C9 112.98(14) . . ?
C12 C11 H11A 109.0 . . ?
C9 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C9 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 111.61(15) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 108.54(14) . . ?
C14 C13 C18 109.45(14) . . ?
C12 C13 C18 111.16(15) . . ?
C14 C13 C17 102.35(12) . . ?
C12 C13 C17 114.07(14) . . ?
C18 C13 C17 110.83(14) . . ?
C8 C14 C13 125.73(15) . . ?
C8 C14 C15 125.33(15) . . ?
C13 C14 C15 108.54(13) . . ?
C14 C15 C16 105.48(14) . . ?
C14 C15 H15A 110.6 . . ?
C16 C15 H15A 110.6 . . ?
C14 C15 H15B 110.6 . . ?
C16 C15 H15B 110.6 . . ?
H15A C15 H15B 108.8 . . ?
C15 C16 C17 106.21(15) . . ?
C15 C16 H16A 110.5 . . ?
C17 C16 H16A 110.5 . . ?
C15 C16 H16B 110.5 . . ?
C17 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
C16 C17 C20 112.69(15) . . ?
C16 C17 C13 103.26(14) . . ?
C20 C17 C13 119.19(13) . . ?
C16 C17 H17A 107.0 . . ?
C20 C17 H17A 107.0 . . ?
C13 C17 H17A 107.0 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19A H19A 109.5 . . ?
C10 C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C10 C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C22 C20 C21 110.55(15) . . ?
C22 C20 C17 109.97(14) . . ?
C21 C20 C17 113.30(14) . . ?
C22 C20 H20A 107.6 . . ?
C21 C20 H20A 107.6 . . ?
C17 C20 H20A 107.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 116.96(16) . . ?
C23 C22 H22A 108.1 . . ?
C20 C22 H22A 108.1 . . ?
C23 C22 H22B 108.1 . . ?
C20 C22 H22B 108.1 . . ?
H22A C22 H22B 107.3 . . ?
C22 C23 C24 111.94(17) . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C25 C24 C23 116.02(17) . . ?
C25 C24 H24A 108.3 . . ?
C23 C24 H24A 108.3 . . ?
C25 C24 H24B 108.3 . . ?
C23 C24 H24B 108.3 . . ?
H24A C24 H24B 107.4 . . ?
C26 C25 C27 111.58(17) . . ?
C26 C25 C24 110.09(17) . . ?
C27 C25 C24 112.55(16) . . ?
C26 C25 H25A 107.5 . . ?
C27 C25 H25A 107.5 . . ?
C24 C25 H25A 107.5 . . ?
O26 C26 C25 112.35(15) . . ?
O26 C26 H26A 109.1 . . ?
C25 C26 H26A 109.1 . . ?
O26 C26 H26B 109.1 . . ?
C25 C26 H26B 109.1 . . ?
H26A C26 H26B 107.9 . . ?
C26 O26 H26 105.8(15) . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 C1 C2 C3 -58.20(19) . . . . ?
C1 C2 C3 O3 -178.78(13) . . . . ?
C1 C2 C3 C4 59.93(18) . . . . ?
O3 C3 C4 C5 178.44(13) . . . . ?
C2 C3 C4 C5 -58.87(18) . . . . ?
C3 C4 C5 C6 -177.28(14) . . . . ?
C3 C4 C5 C10 55.96(18) . . . . ?
C4 C5 C6 C7 174.43(13) . . . . ?
C10 C5 C6 C7 -57.08(17) . . . . ?
C5 C6 C7 C8 43.96(19) . . . . ?
C6 C7 C8 C14 149.30(15) . . . . ?
C6 C7 C8 C9 -38.97(18) . . . . ?
C14 C8 C9 C11 -11.2(2) . . . . ?
C7 C8 C9 C11 177.08(16) . . . . ?
C14 C8 C9 C10 -141.35(15) . . . . ?
C7 C8 C9 C10 46.94(17) . . . . ?
C2 C1 C10 C19A -69.73(18) . . . . ?
C2 C1 C10 C5 52.03(18) . . . . ?
C2 C1 C10 C9 168.36(13) . . . . ?
C6 C5 C10 C19A -58.15(18) . . . . ?
C4 C5 C10 C19A 69.94(16) . . . . ?
C6 C5 C10 C1 -178.91(16) . . . . ?
C4 C5 C10 C1 -50.82(16) . . . . ?
C6 C5 C10 C9 63.23(16) . . . . ?
C4 C5 C10 C9 -168.68(12) . . . . ?
C11 C9 C10 C19A -65.20(19) . . . . ?
C8 C9 C10 C19A 63.81(17) . . . . ?
C11 C9 C10 C1 56.06(19) . . . . ?
C8 C9 C10 C1 -174.93(13) . . . . ?
C11 C9 C10 C5 173.07(14) . . . . ?
C8 C9 C10 C5 -57.92(15) . . . . ?
C8 C9 C11 C12 39.2(2) . . . . ?
C10 C9 C11 C12 168.48(15) . . . . ?
C9 C11 C12 C13 -60.6(2) . . . . ?
C11 C12 C13 C14 48.9(2) . . . . ?
C11 C12 C13 C18 -71.6(2) . . . . ?
C11 C12 C13 C17 162.24(15) . . . . ?
C7 C8 C14 C13 174.42(14) . . . . ?
C9 C8 C14 C13 3.3(2) . . . . ?
C7 C8 C14 C15 2.5(2) . . . . ?
C9 C8 C14 C15 -168.67(15) . . . . ?
C12 C13 C14 C8 -22.0(2) . . . . ?
C18 C13 C14 C8 99.49(18) . . . . ?
C17 C13 C14 C8 -142.91(16) . . . . ?
C12 C13 C14 C15 151.07(15) . . . . ?
C18 C13 C14 C15 -87.45(16) . . . . ?
C17 C13 C14 C15 30.16(15) . . . . ?
C8 C14 C15 C16 162.35(15) . . . . ?
C13 C14 C15 C16 -10.75(17) . . . . ?
C14 C15 C16 C17 -13.45(18) . . . . ?
C15 C16 C17 C20 161.74(14) . . . . ?
C15 C16 C17 C13 31.83(18) . . . . ?
C14 C13 C17 C16 -37.46(16) . . . . ?
C12 C13 C17 C16 -154.47(15) . . . . ?
C18 C13 C17 C16 79.16(16) . . . . ?
C14 C13 C17 C20 -163.31(13) . . . . ?
C12 C13 C17 C20 79.68(19) . . . . ?
C18 C13 C17 C20 -46.7(2) . . . . ?
C16 C17 C20 C22 61.58(19) . . . . ?
C13 C17 C20 C22 -177.19(15) . . . . ?
C16 C17 C20 C21 -174.15(14) . . . . ?
C13 C17 C20 C21 -52.9(2) . . . . ?
C21 C20 C22 C23 58.5(2) . . . . ?
C17 C20 C22 C23 -175.64(15) . . . . ?
C20 C22 C23 C24 176.95(16) . . . . ?
C22 C23 C24 C25 177.76(16) . . . . ?
C23 C24 C25 C26 168.33(17) . . . . ?
C23 C24 C25 C27 -66.5(2) . . . . ?
C27 C25 C26 O26 -63.6(2) . . . . ?
C24 C25 C26 O26 62.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.48
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.030

# Attachment 'kno45.cif'

data_shelxl2
_database_code_depnum_ccdc_archive 'CCDC 867380'
#TrackingRef 'kno45.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C27 H44 O2'

_chemical_formula_sum            'C27 H44 O2'

_chemical_formula_weight         400.62

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source

C C 0.0033 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'

_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   P2(1)

_symmetry_space_group_name_Hall  'P 2yb'

loop_

_symmetry_equiv_pos_as_xyz

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

_cell_length_a                   11.658(3)

_cell_length_b                   6.105(2)

_cell_length_c                   17.568(5)

_cell_angle_alpha                90.00

_cell_angle_beta                 106.10(2)

_cell_angle_gamma                90.00

_cell_volume                     1201.3(6)

_cell_formula_units_Z            2

_cell_measurement_temperature    150(2)

_cell_measurement_reflns_used    2553

_cell_measurement_theta_min      2.45

_cell_measurement_theta_max      21.88

_exptl_crystal_description       plate

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.63

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.04

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.108

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             444

_exptl_absorpt_coefficient_mu    0.067

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9590

_exptl_absorpt_correction_T_max  0.9973

_exptl_absorpt_process_details   
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)'

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      150(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_wavelength_id  x-ray

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_device       'Bruker Kappa APEX II CCD'

_diffrn_measurement_method       '0.5 deg frames in phi and omega'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            18278

_diffrn_reflns_av_R_equivalents  0.1437

_diffrn_reflns_av_sigmaI/netI    0.1412

_diffrn_reflns_limit_h_min       -14

_diffrn_reflns_limit_h_max       14

_diffrn_reflns_limit_k_min       -7

_diffrn_reflns_limit_k_max       7

_diffrn_reflns_limit_l_min       -21

_diffrn_reflns_limit_l_max       22

_diffrn_reflns_theta_min         1.21

_diffrn_reflns_theta_max         27.00

_reflns_number_total             5131

_reflns_number_gt                2923

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)'
_computing_cell_refinement       'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)'
_computing_data_reduction        'SAINT NT v6.0 (Bruker AXS, 2003)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)'

_refine_special_details          
;

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F^2^, conventional R-factors R are based

on F, with F set to zero for negative F^2^. The threshold expression of

F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F^2^ 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/[\s^2^(Fo^2^)+(0.0027P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     none

_refine_ls_extinction_coef       ?

_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   -0.7(17)

_refine_ls_number_reflns         5131

_refine_ls_number_parameters     274

_refine_ls_number_restraints     1

_refine_ls_R_factor_all          0.1092

_refine_ls_R_factor_gt           0.0534

_refine_ls_wR_factor_ref         0.0957

_refine_ls_wR_factor_gt          0.0850

_refine_ls_goodness_of_fit_ref   0.922

_refine_ls_restrained_S_all      0.922

_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 0.2391(2) 0.7661(4) 0.29643(14) 0.0266(7) Uani 1 1 d . . .
H1A H 0.3218 0.7199 0.3234 0.032 Uiso 1 1 calc R . .
H1B H 0.1845 0.6610 0.3114 0.032 Uiso 1 1 calc R . .
C2 C 0.2205(2) 0.7523(5) 0.20770(13) 0.0308(7) Uani 1 1 d . . .
H2A H 0.2799 0.8455 0.1923 0.037 Uiso 1 1 calc R . .
H2B H 0.2319 0.5993 0.1926 0.037 Uiso 1 1 calc R . .
C3 C 0.0961(2) 0.8277(5) 0.16489(14) 0.0326(7) Uani 1 1 d . . .
H3A H 0.0363 0.7316 0.1797 0.039 Uiso 1 1 calc R . .
O3 O 0.07693(17) 0.8226(4) 0.08059(11) 0.0388(6) Uani 1 1 d . . .
H3 H 0.093(3) 0.695(5) 0.0700(19) 0.067(13) Uiso 1 1 d . . .
C4 C 0.0781(2) 1.0629(4) 0.18668(15) 0.0301(7) Uani 1 1 d . . .
H4A H 0.1299 1.1593 0.1652 0.036 Uiso 1 1 calc R . .
H4B H -0.0058 1.1055 0.1615 0.036 Uiso 1 1 calc R . .
C5 C 0.1059(2) 1.0983(4) 0.27483(14) 0.0240(7) Uani 1 1 d . . .
C6 C 0.0453(2) 1.2406(4) 0.30513(14) 0.0259(7) Uani 1 1 d . . .
H6A H -0.0205 1.3147 0.2706 0.031 Uiso 1 1 calc R . .
C7 C 0.0757(2) 1.2873(5) 0.38896(14) 0.0253(6) Uani 1 1 d . . .
H7A H 0.0403 1.4099 0.4069 0.030 Uiso 1 1 calc R . .
C8 C 0.1517(2) 1.1629(4) 0.44145(14) 0.0199(6) Uani 1 1 d . . .
C9 C 0.2074(2) 0.9669(4) 0.41236(14) 0.0227(7) Uani 1 1 d . . .
H9A H 0.1500 0.8436 0.4096 0.027 Uiso 1 1 calc R . .
C10 C 0.2183(2) 0.9937(4) 0.32697(14) 0.0207(6) Uani 1 1 d . . .
C11 C 0.3249(2) 0.8917(5) 0.47117(13) 0.0268(7) Uani 1 1 d . . .
H11A H 0.3408 0.7388 0.4582 0.032 Uiso 1 1 calc R . .
H11B H 0.3906 0.9836 0.4633 0.032 Uiso 1 1 calc R . .
C12 C 0.3277(2) 0.9018(4) 0.55881(13) 0.0253(7) Uani 1 1 d . . .
H12A H 0.2729 0.7897 0.5696 0.030 Uiso 1 1 calc R . .
H12B H 0.4094 0.8671 0.5918 0.030 Uiso 1 1 calc R . .
C13 C 0.2918(2) 1.1244(4) 0.58185(14) 0.0199(6) Uani 1 1 d . . .
C14 C 0.16489(19) 1.1690(4) 0.52816(13) 0.0207(6) Uani 1 1 d . . .
H14A H 0.1159 1.0433 0.5380 0.025 Uiso 1 1 calc R . .
C15 C 0.1205(2) 1.3636(5) 0.56388(13) 0.0300(7) Uani 1 1 d . . .
H15A H 0.0324 1.3615 0.5519 0.036 Uiso 1 1 calc R . .
H15B H 0.1455 1.5021 0.5439 0.036 Uiso 1 1 calc R . .
C16 C 0.1792(2) 1.3381(5) 0.65338(14) 0.0327(7) Uani 1 1 d . . .
H16A H 0.1179 1.3078 0.6813 0.039 Uiso 1 1 calc R . .
H16B H 0.2221 1.4739 0.6754 0.039 Uiso 1 1 calc R . .
C17 C 0.2675(2) 1.1444(5) 0.66377(14) 0.0260(6) Uani 1 1 d . . .
H17A H 0.2230 1.0097 0.6712 0.031 Uiso 1 1 calc R . .
C18 C 0.37901(19) 1.3012(4) 0.57154(14) 0.0263(6) Uani 1 1 d . . .
H18A H 0.4609 1.2551 0.5980 0.039 Uiso 1 1 calc R . .
H18B H 0.3617 1.4386 0.5950 0.039 Uiso 1 1 calc R . .
H18C H 0.3704 1.3233 0.5150 0.039 Uiso 1 1 calc R . .
C19 C 0.3218(2) 1.1482(5) 0.32459(14) 0.0282(7) Uani 1 1 d . . .
H19A H 0.3180 1.1818 0.2694 0.042 Uiso 1 1 calc R . .
H19B H 0.3981 1.0770 0.3502 0.042 Uiso 1 1 calc R . .
H19C H 0.3152 1.2842 0.3527 0.042 Uiso 1 1 calc R . .
C20 C 0.3732(2) 1.1685(5) 0.73816(13) 0.0261(7) Uani 1 1 d . . .
H20A H 0.4152 1.3087 0.7337 0.031 Uiso 1 1 calc R . .
C21 C 0.4637(2) 0.9810(5) 0.74778(16) 0.0400(8) Uani 1 1 d . . .
H21A H 0.5249 0.9964 0.7986 0.060 Uiso 1 1 calc R . .
H21B H 0.5016 0.9864 0.7045 0.060 Uiso 1 1 calc R . .
H21C H 0.4226 0.8405 0.7465 0.060 Uiso 1 1 calc R . .
C22 C 0.3276(2) 1.1824(5) 0.81185(13) 0.0328(7) Uani 1 1 d . . .
H22A H 0.2563 1.2782 0.7999 0.039 Uiso 1 1 calc R . .
H22B H 0.3023 1.0344 0.8237 0.039 Uiso 1 1 calc R . .
C23 C 0.4185(2) 1.2697(5) 0.88494(14) 0.0369(8) Uani 1 1 d . . .
H23A H 0.4357 1.4248 0.8759 0.044 Uiso 1 1 calc R . .
H23B H 0.4937 1.1862 0.8931 0.044 Uiso 1 1 calc R . .
C24 C 0.3764(2) 1.2540(5) 0.95992(14) 0.0370(8) Uani 1 1 d . . .
H24A H 0.3660 1.0974 0.9710 0.044 Uiso 1 1 calc R . .
H24B H 0.4400 1.3132 1.0049 0.044 Uiso 1 1 calc R . .
C25 C 0.2604(2) 1.3740(5) 0.95643(14) 0.0281(7) Uani 1 1 d . . .
H25A H 0.1964 1.3149 0.9107 0.034 Uiso 1 1 calc R . .
C26 C 0.2271(2) 1.3220(5) 1.03274(14) 0.0362(7) Uani 1 1 d . . .
H26A H 0.2193 1.1614 1.0372 0.043 Uiso 1 1 calc R . .
H26B H 0.2924 1.3716 1.0786 0.043 Uiso 1 1 calc R . .
O27 O 0.11846(18) 1.4236(3) 1.03591(11) 0.0376(6) Uani 1 1 d . . .
H27 H 0.058(3) 1.371(6) 0.9934(18) 0.071(11) Uiso 1 1 d . . .
C28 C 0.2695(2) 1.6179(5) 0.94525(17) 0.0444(8) Uani 1 1 d . . .
H28A H 0.1942 1.6880 0.9461 0.067 Uiso 1 1 calc R . .
H28B H 0.2854 1.6467 0.8942 0.067 Uiso 1 1 calc R . .
H28C H 0.3347 1.6775 0.9881 0.067 Uiso 1 1 calc R . .

loop_

_atom_site_aniso_label

_atom_site_aniso_U_11

_atom_site_aniso_U_22

_atom_site_aniso_U_33

_atom_site_aniso_U_23

_atom_site_aniso_U_13

_atom_site_aniso_U_12

C1 0.0277(15) 0.0246(18) 0.0265(16) -0.0002(13) 0.0059(11) 0.0029(13)
C2 0.0363(16) 0.0295(18) 0.0272(16) -0.0037(14) 0.0096(12) 0.0070(13)
C3 0.0353(16) 0.039(2) 0.0220(16) 0.0012(15) 0.0056(12) 0.0031(15)
O3 0.0487(13) 0.0460(17) 0.0192(11) -0.0026(11) 0.0053(9) 0.0089(12)
C4 0.0294(16) 0.036(2) 0.0251(17) 0.0055(14) 0.0080(13) 0.0052(13)
C5 0.0233(15) 0.0219(17) 0.0255(16) 0.0027(13) 0.0049(12) 0.0008(12)
C6 0.0257(14) 0.0263(18) 0.0251(16) 0.0059(13) 0.0060(11) 0.0059(12)
C7 0.0270(14) 0.0230(17) 0.0299(16) 0.0015(14) 0.0145(12) 0.0052(13)
C8 0.0164(13) 0.0196(16) 0.0239(15) 0.0004(13) 0.0059(11) -0.0041(12)
C9 0.0247(14) 0.0205(18) 0.0238(16) 0.0015(12) 0.0081(11) 0.0003(12)
C10 0.0256(15) 0.0159(16) 0.0223(16) 0.0024(12) 0.0093(11) -0.0001(12)
C11 0.0337(15) 0.0236(17) 0.0238(15) 0.0032(13) 0.0089(12) 0.0095(13)
C12 0.0310(15) 0.0227(17) 0.0226(16) 0.0014(13) 0.0080(12) 0.0021(13)
C13 0.0198(14) 0.0156(16) 0.0252(15) 0.0013(13) 0.0074(11) 0.0013(12)
C14 0.0192(13) 0.0197(16) 0.0255(16) -0.0007(13) 0.0101(11) -0.0017(12)
C15 0.0262(14) 0.037(2) 0.0275(16) -0.0020(14) 0.0082(11) 0.0079(13)
C16 0.0257(14) 0.044(2) 0.0282(16) -0.0058(15) 0.0070(12) 0.0086(14)
C17 0.0256(14) 0.0276(17) 0.0244(15) -0.0007(14) 0.0061(12) -0.0009(14)
C18 0.0212(13) 0.0235(17) 0.0333(15) 0.0003(14) 0.0061(11) -0.0006(13)
C19 0.0295(15) 0.0273(18) 0.0285(16) 0.0047(14) 0.0090(12) -0.0004(14)
C20 0.0261(14) 0.0295(18) 0.0229(15) -0.0009(14) 0.0070(11) -0.0001(13)
C21 0.0368(17) 0.049(2) 0.0308(17) 0.0020(16) 0.0040(14) 0.0112(16)
C22 0.0308(15) 0.044(2) 0.0232(16) -0.0062(15) 0.0061(12) 0.0001(14)
C23 0.0342(16) 0.053(2) 0.0225(15) -0.0049(15) 0.0054(12) 0.0022(15)
C24 0.0399(17) 0.049(2) 0.0191(16) -0.0020(15) 0.0036(12) 0.0058(15)
C25 0.0316(15) 0.035(2) 0.0172(15) -0.0027(13) 0.0062(11) -0.0007(14)
C26 0.0407(17) 0.042(2) 0.0265(16) 0.0012(15) 0.0104(12) 0.0039(16)
O27 0.0356(12) 0.0487(15) 0.0287(12) -0.0108(11) 0.0092(10) -0.0020(11)
C28 0.048(2) 0.040(2) 0.0436(19) 0.0045(17) 0.0105(15) 0.0007(17)

_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 C2 1.515(3) . ?
C1 C10 1.533(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.508(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O3 1.435(3) . ?
C3 C4 1.515(4) . ?
C3 H3A 1.0000 . ?
O3 H3 0.84(3) . ?
C4 C5 1.507(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.321(3) . ?
C5 C10 1.517(3) . ?
C6 C7 1.444(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.327(3) . ?
C7 H7A 0.9500 . ?
C8 C14 1.489(3) . ?
C8 C9 1.516(3) . ?
C9 C11 1.539(3) . ?
C9 C10 1.549(3) . ?
C9 H9A 1.0000 . ?
C10 C19 1.541(3) . ?
C11 C12 1.532(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.510(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.528(3) . ?
C13 C14 1.542(3) . ?
C13 C17 1.547(3) . ?
C14 C15 1.501(3) . ?
C14 H14A 1.0000 . ?
C15 C16 1.539(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.545(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C20 1.535(3) . ?
C17 H17A 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C22 1.533(3) . ?
C20 C21 1.534(4) . ?
C20 H20A 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.517(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.531(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.524(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C28 1.510(4) . ?
C25 C26 1.529(3) . ?
C25 H25A 1.0000 . ?
C26 O27 1.425(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
O27 H27 0.93(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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

C2 C1 C10 114.8(2) . . ?
C2 C1 H1A 108.6 . . ?
C10 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
C10 C1 H1B 108.6 . . ?
H1A C1 H1B 107.5 . . ?
C3 C2 C1 109.9(2) . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
O3 C3 C2 111.2(2) . . ?
O3 C3 C4 106.8(2) . . ?
C2 C3 C4 110.2(2) . . ?
O3 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C3 O3 H3 106(2) . . ?
C5 C4 C3 113.0(2) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 C10 120.2(2) . . ?
C4 C5 C10 117.6(2) . . ?
C5 C6 C7 122.2(2) . . ?
C5 C6 H6A 118.9 . . ?
C7 C6 H6A 118.9 . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 H7A 119.2 . . ?
C6 C7 H7A 119.2 . . ?
C7 C8 C14 123.8(2) . . ?
C7 C8 C9 118.9(2) . . ?
C14 C8 C9 115.6(2) . . ?
C8 C9 C11 113.2(2) . . ?
C8 C9 C10 113.6(2) . . ?
C11 C9 C10 112.6(2) . . ?
C8 C9 H9A 105.5 . . ?
C11 C9 H9A 105.5 . . ?
C10 C9 H9A 105.5 . . ?
C5 C10 C1 111.4(2) . . ?
C5 C10 C19 106.1(2) . . ?
C1 C10 C19 110.2(2) . . ?
C5 C10 C9 109.9(2) . . ?
C1 C10 C9 107.9(2) . . ?
C19 C10 C9 111.5(2) . . ?
C12 C11 C9 115.5(2) . . ?
C12 C11 H11A 108.4 . . ?
C9 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C9 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 112.0(2) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C18 111.2(2) . . ?
C12 C13 C14 106.6(2) . . ?
C18 C13 C14 111.1(2) . . ?
C12 C13 C17 117.2(2) . . ?
C18 C13 C17 110.7(2) . . ?
C14 C13 C17 99.39(18) . . ?
C8 C14 C15 119.9(2) . . ?
C8 C14 C13 115.50(19) . . ?
C15 C14 C13 105.52(19) . . ?
C8 C14 H14A 104.8 . . ?
C15 C14 H14A 104.8 . . ?
C13 C14 H14A 104.8 . . ?
C14 C15 C16 103.9(2) . . ?
C14 C15 H15A 111.0 . . ?
C16 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C15 C16 C17 106.9(2) . . ?
C15 C16 H16A 110.3 . . ?
C17 C16 H16A 110.3 . . ?
C15 C16 H16B 110.3 . . ?
C17 C16 H16B 110.3 . . ?
H16A C16 H16B 108.6 . . ?
C20 C17 C16 112.3(2) . . ?
C20 C17 C13 119.27(19) . . ?
C16 C17 C13 103.8(2) . . ?
C20 C17 H17A 107.0 . . ?
C16 C17 H17A 107.0 . . ?
C13 C17 H17A 107.0 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C20 C21 109.7(2) . . ?
C22 C20 C17 109.8(2) . . ?
C21 C20 C17 112.8(2) . . ?
C22 C20 H20A 108.1 . . ?
C21 C20 H20A 108.1 . . ?
C17 C20 H20A 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 114.2(2) . . ?
C23 C22 H22A 108.7 . . ?
C20 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C20 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 C24 113.0(2) . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C25 C24 C23 115.3(2) . . ?
C25 C24 H24A 108.4 . . ?
C23 C24 H24A 108.4 . . ?
C25 C24 H24B 108.4 . . ?
C23 C24 H24B 108.4 . . ?
H24A C24 H24B 107.5 . . ?
C28 C25 C24 112.7(2) . . ?
C28 C25 C26 111.3(2) . . ?
C24 C25 C26 107.7(2) . . ?
C28 C25 H25A 108.4 . . ?
C24 C25 H25A 108.4 . . ?
C26 C25 H25A 108.4 . . ?
O27 C26 C25 112.9(2) . . ?
O27 C26 H26A 109.0 . . ?
C25 C26 H26A 109.0 . . ?
O27 C26 H26B 109.0 . . ?
C25 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C26 O27 H27 107.5(18) . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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 C1 C2 C3 -56.8(3) . . . . ?
C1 C2 C3 O3 178.3(2) . . . . ?
C1 C2 C3 C4 60.1(3) . . . . ?
O3 C3 C4 C5 -175.0(2) . . . . ?
C2 C3 C4 C5 -54.1(3) . . . . ?
C3 C4 C5 C6 -145.6(3) . . . . ?
C3 C4 C5 C10 44.2(3) . . . . ?
C4 C5 C6 C7 -175.8(2) . . . . ?
C10 C5 C6 C7 -5.9(4) . . . . ?
C5 C6 C7 C8 -12.2(4) . . . . ?
C6 C7 C8 C14 -164.9(2) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C7 C8 C9 C11 158.0(2) . . . . ?
C14 C8 C9 C11 -36.1(3) . . . . ?
C7 C8 C9 C10 27.9(3) . . . . ?
C14 C8 C9 C10 -166.2(2) . . . . ?
C6 C5 C10 C1 151.6(2) . . . . ?
C4 C5 C10 C1 -38.1(3) . . . . ?
C6 C5 C10 C19 -88.5(3) . . . . ?
C4 C5 C10 C19 81.8(3) . . . . ?
C6 C5 C10 C9 32.1(3) . . . . ?
C4 C5 C10 C9 -157.6(2) . . . . ?
C2 C1 C10 C5 44.4(3) . . . . ?
C2 C1 C10 C19 -73.1(3) . . . . ?
C2 C1 C10 C9 165.0(2) . . . . ?
C8 C9 C10 C5 -41.6(3) . . . . ?
C11 C9 C10 C5 -172.0(2) . . . . ?
C8 C9 C10 C1 -163.2(2) . . . . ?
C11 C9 C10 C1 66.4(3) . . . . ?
C8 C9 C10 C19 75.8(3) . . . . ?
C11 C9 C10 C19 -54.6(3) . . . . ?
C8 C9 C11 C12 38.7(3) . . . . ?
C10 C9 C11 C12 169.3(2) . . . . ?
C9 C11 C12 C13 -52.3(3) . . . . ?
C11 C12 C13 C18 -62.7(3) . . . . ?
C11 C12 C13 C14 58.5(3) . . . . ?
C11 C12 C13 C17 168.6(2) . . . . ?
C7 C8 C14 C15 -19.1(4) . . . . ?
C9 C8 C14 C15 175.8(2) . . . . ?
C7 C8 C14 C13 -147.1(2) . . . . ?
C9 C8 C14 C13 47.7(3) . . . . ?
C12 C13 C14 C8 -57.7(3) . . . . ?
C18 C13 C14 C8 63.5(3) . . . . ?
C17 C13 C14 C8 -179.8(2) . . . . ?
C12 C13 C14 C15 167.5(2) . . . . ?
C18 C13 C14 C15 -71.3(2) . . . . ?
C17 C13 C14 C15 45.3(2) . . . . ?
C8 C14 C15 C16 -165.2(2) . . . . ?
C13 C14 C15 C16 -32.8(3) . . . . ?
C14 C15 C16 C17 7.0(3) . . . . ?
C15 C16 C17 C20 151.0(2) . . . . ?
C15 C16 C17 C13 20.9(3) . . . . ?
C12 C13 C17 C20 80.7(3) . . . . ?
C18 C13 C17 C20 -48.2(3) . . . . ?
C14 C13 C17 C20 -165.1(2) . . . . ?
C12 C13 C17 C16 -153.6(2) . . . . ?
C18 C13 C17 C16 77.5(2) . . . . ?
C14 C13 C17 C16 -39.3(2) . . . . ?
C16 C17 C20 C22 59.1(3) . . . . ?
C13 C17 C20 C22 -179.3(3) . . . . ?
C16 C17 C20 C21 -178.1(2) . . . . ?
C13 C17 C20 C21 -56.5(3) . . . . ?
C21 C20 C22 C23 71.9(3) . . . . ?
C17 C20 C22 C23 -163.6(2) . . . . ?
C20 C22 C23 C24 -172.5(3) . . . . ?
C22 C23 C24 C25 -58.4(4) . . . . ?
C23 C24 C25 C28 -62.2(3) . . . . ?
C23 C24 C25 C26 174.8(2) . . . . ?
C28 C25 C26 O27 56.8(3) . . . . ?
C24 C25 C26 O27 -179.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        27.00

_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.160

_refine_diff_density_min         -0.201

_refine_diff_density_rms         0.046