# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 926020'
#TrackingRef '3o.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 O'
_chemical_formula_weight         284.42
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           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   6.8754(3)
_cell_length_b                   10.7487(5)
_cell_length_c                   11.7991(6)
_cell_angle_alpha                91.303(3)
_cell_angle_beta                 92.041(3)
_cell_angle_gamma                99.150(3)
_cell_volume                     859.97(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9871
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      298(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7200
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3146
_reflns_number_gt                2319
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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^)+(0.1309P)^2^+0.4396P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3146
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2331
_refine_ls_wR_factor_gt          0.2132
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_iucr_refine_instruction_details 
;
TITL TRY1 in P-1
CELL 0.71073 6.8754 10.7487 11.7991 91.303 92.041 99.150
ZERR 2.00 0.0003 0.0005 0.0006 0.003 0.003 0.003
LATT 1
SFAC C H O
UNIT 40 56 2
L.S. 12
ACTA
BOND $H
HTAB
CONF
SIZE 0.2 0.1 0.1
TEMP 25
MERG 2
FMAP 2
PLAN 10
WGHT 0.130900 0.439600
FVAR 0.32187
O1 3 0.229448 -0.094357 1.063849 11.00000 0.06246 0.04532 =
0.03578 0.00061 0.00265 0.00600
C1 1 -0.022126 -0.379248 0.866348 11.00000 0.08038 0.05782 =
0.11472 0.02818 -0.01260 -0.01595
AFIX 137
H1A 2 -0.014362 -0.386602 0.785457 11.00000 -1.50000
H1B 2 -0.131494 -0.337888 0.884352 11.00000 -1.50000
H1C 2 -0.040345 -0.461740 0.897695 11.00000 -1.50000
AFIX 0
C2 1 0.166254 -0.303019 0.915933 11.00000 0.06837 0.03648 =
0.04591 0.00309 0.00330 0.00815
AFIX 13
H2 2 0.154221 -0.298338 0.998374 11.00000 -1.20000
AFIX 0
C3 1 0.197954 -0.168807 0.874463 11.00000 0.04166 0.03613 =
0.04190 0.00096 0.00340 0.00707
C4 1 0.199385 -0.144894 0.759367 11.00000 0.05685 0.03302 =
0.04330 -0.00714 0.00069 0.00539
AFIX 43
H4 2 0.179489 -0.212120 0.706998 11.00000 -1.20000
AFIX 0
C5 1 0.229875 -0.022851 0.721126 11.00000 0.05061 0.03703 =
0.03834 -0.00189 0.00095 0.00314
C6 1 0.239983 0.027942 0.607982 11.00000 0.07197 0.04383 =
0.03815 -0.00191 -0.00115 0.00038
AFIX 43
H6 2 0.224469 -0.020581 0.541037 11.00000 -1.20000
AFIX 0
C7 1 0.274633 0.153959 0.613299 11.00000 0.06112 0.04295 =
0.03995 0.00235 -0.00307 0.00111
C8 1 0.317095 0.243593 0.516710 11.00000 0.06209 0.04812 =
0.04225 0.01045 0.00221 0.00401
C9 1 0.314263 0.170485 0.403799 11.00000 0.10150 0.06749 =
0.04397 0.00938 0.01378 0.01229
AFIX 137
H9A 2 0.407382 0.112879 0.408604 11.00000 -1.50000
H9B 2 0.349078 0.228433 0.344356 11.00000 -1.50000
H9C 2 0.184552 0.124248 0.387555 11.00000 -1.50000
AFIX 0
C10 1 0.258363 0.006718 1.145772 11.00000 0.05257 0.05272 =
0.03676 -0.00408 0.00017 0.00865
AFIX 137
H10A 2 0.385128 0.057030 1.137072 11.00000 -1.50000
H10B 2 0.252221 -0.026631 1.220580 11.00000 -1.50000
H10C 2 0.157252 0.057959 1.134945 11.00000 -1.50000
AFIX 0
C11 1 0.230523 -0.065294 0.951525 11.00000 0.03536 0.04059 =
0.03806 0.00059 0.00361 0.00517
C12 1 0.343190 -0.366418 0.893090 11.00000 0.08893 0.05112 =
0.10864 0.01191 0.00562 0.02496
AFIX 137
H12A 2 0.326970 -0.447243 0.927610 11.00000 -1.50000
H12B 2 0.460485 -0.314882 0.924466 11.00000 -1.50000
H12C 2 0.354223 -0.377300 0.812720 11.00000 -1.50000
AFIX 0
C13 1 0.261861 0.078561 0.799062 11.00000 0.03964 0.03461 =
0.04292 -0.00088 0.00103 0.00443
C14 1 0.290341 0.201436 0.736539 11.00000 0.05507 0.03505 =
0.03998 0.00100 0.00059 0.00387
C15 1 0.520889 0.320910 0.542996 11.00000 0.06511 0.05791 =
0.09941 0.01357 0.00538 -0.00244
AFIX 23
H15A 2 0.543872 0.389117 0.490237 11.00000 -1.20000
H15B 2 0.620675 0.267688 0.532517 11.00000 -1.20000
AFIX 0
C16 1 0.541034 0.378151 0.669735 11.00000 0.08971 0.07136 =
0.09054 0.01408 -0.00754 -0.01671
AFIX 23
H16A 2 0.674509 0.422208 0.683654 11.00000 -1.20000
H16B 2 0.452671 0.439626 0.676542 11.00000 -1.20000
AFIX 0
C17 1 0.494385 0.278858 0.762479 11.00000 0.06377 0.04890 =
0.06004 0.00654 -0.00598 -0.00661
AFIX 23
H17A 2 0.593153 0.223682 0.764098 11.00000 -1.20000
H17B 2 0.497189 0.320883 0.836283 11.00000 -1.20000
AFIX 0
C18 1 0.162279 0.331178 0.506971 11.00000 0.07730 0.06503 =
0.06800 0.00727 -0.00234 0.01340
AFIX 137
H18A 2 0.035690 0.282250 0.487491 11.00000 -1.50000
H18B 2 0.197551 0.391054 0.449089 11.00000 -1.50000
H18C 2 0.156591 0.375109 0.578231 11.00000 -1.50000
AFIX 0
C19 1 0.127544 0.278496 0.768314 11.00000 0.07933 0.04796 =
0.10492 0.01293 0.01315 0.01984
AFIX 137
H19A 2 0.000513 0.230117 0.748893 11.00000 -1.50000
H19B 2 0.143567 0.355425 0.727425 11.00000 -1.50000
H19C 2 0.137460 0.297796 0.848355 11.00000 -1.50000
AFIX 0
C20 1 0.261199 0.058319 0.914188 11.00000 0.04503 0.03638 =
0.03994 -0.00502 0.00158 0.00356
AFIX 43
H20 2 0.280891 0.126011 0.966064 11.00000 -1.20000
HKLF 4
END
;
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 0.2294(3) -0.09436(16) 1.06385(14) 0.0481(5) Uani 1 1 d . . .
C1 C -0.0221(5) -0.3792(3) 0.8663(4) 0.0872(12) Uani 1 1 d . . .
H1A H -0.0144 -0.3866 0.7855 0.131 Uiso 1 1 calc R . .
H1B H -0.1315 -0.3379 0.8844 0.131 Uiso 1 1 calc R . .
H1C H -0.0403 -0.4617 0.8977 0.131 Uiso 1 1 calc R . .
C2 C 0.1663(4) -0.3030(2) 0.9159(2) 0.0502(7) Uani 1 1 d . . .
H2 H 0.1542 -0.2983 0.9984 0.060 Uiso 1 1 calc R . .
C3 C 0.1980(3) -0.1688(2) 0.8745(2) 0.0398(6) Uani 1 1 d . . .
C4 C 0.1994(4) -0.1449(2) 0.7594(2) 0.0447(6) Uani 1 1 d . . .
H4 H 0.1795 -0.2121 0.7070 0.054 Uiso 1 1 calc R . .
C5 C 0.2299(4) -0.0229(2) 0.7211(2) 0.0425(6) Uani 1 1 d . . .
C6 C 0.2400(4) 0.0279(2) 0.6080(2) 0.0524(7) Uani 1 1 d . . .
H6 H 0.2245 -0.0206 0.5410 0.063 Uiso 1 1 calc R . .
C7 C 0.2746(4) 0.1540(2) 0.6133(2) 0.0489(7) Uani 1 1 d . . .
C8 C 0.3171(4) 0.2436(2) 0.5167(2) 0.0512(7) Uani 1 1 d . . .
C9 C 0.3143(6) 0.1705(3) 0.4038(2) 0.0707(9) Uani 1 1 d . . .
H9A H 0.4074 0.1129 0.4086 0.106 Uiso 1 1 calc R . .
H9B H 0.3491 0.2284 0.3444 0.106 Uiso 1 1 calc R . .
H9C H 0.1846 0.1242 0.3876 0.106 Uiso 1 1 calc R . .
C10 C 0.2584(4) 0.0067(2) 1.1458(2) 0.0474(6) Uani 1 1 d . . .
H10A H 0.3851 0.0570 1.1371 0.071 Uiso 1 1 calc R . .
H10B H 0.2522 -0.0266 1.2206 0.071 Uiso 1 1 calc R . .
H10C H 0.1573 0.0580 1.1349 0.071 Uiso 1 1 calc R . .
C11 C 0.2305(3) -0.0653(2) 0.95152(19) 0.0381(6) Uani 1 1 d . . .
C12 C 0.3432(6) -0.3664(3) 0.8931(4) 0.0812(11) Uani 1 1 d . . .
H12A H 0.3270 -0.4472 0.9276 0.122 Uiso 1 1 calc R . .
H12B H 0.4605 -0.3149 0.9245 0.122 Uiso 1 1 calc R . .
H12C H 0.3542 -0.3773 0.8127 0.122 Uiso 1 1 calc R . .
C13 C 0.2619(3) 0.0786(2) 0.7991(2) 0.0393(6) Uani 1 1 d . . .
C14 C 0.2903(4) 0.2014(2) 0.7365(2) 0.0438(6) Uani 1 1 d . . .
C15 C 0.5209(5) 0.3209(3) 0.5430(3) 0.0753(10) Uani 1 1 d . . .
H15A H 0.5439 0.3891 0.4902 0.090 Uiso 1 1 calc R . .
H15B H 0.6207 0.2677 0.5325 0.090 Uiso 1 1 calc R . .
C16 C 0.5410(6) 0.3782(3) 0.6697(3) 0.0872(12) Uani 1 1 d . . .
H16A H 0.6745 0.4222 0.6837 0.105 Uiso 1 1 calc R . .
H16B H 0.4527 0.4396 0.6765 0.105 Uiso 1 1 calc R . .
C17 C 0.4944(4) 0.2789(3) 0.7625(3) 0.0594(8) Uani 1 1 d . . .
H17A H 0.5932 0.2237 0.7641 0.071 Uiso 1 1 calc R . .
H17B H 0.4972 0.3209 0.8363 0.071 Uiso 1 1 calc R . .
C18 C 0.1623(5) 0.3312(3) 0.5070(3) 0.0699(9) Uani 1 1 d . . .
H18A H 0.0357 0.2823 0.4875 0.105 Uiso 1 1 calc R . .
H18B H 0.1976 0.3911 0.4491 0.105 Uiso 1 1 calc R . .
H18C H 0.1566 0.3751 0.5782 0.105 Uiso 1 1 calc R . .
C19 C 0.1275(5) 0.2785(3) 0.7683(3) 0.0760(10) Uani 1 1 d . . .
H19A H 0.0005 0.2301 0.7489 0.114 Uiso 1 1 calc R . .
H19B H 0.1436 0.3554 0.7274 0.114 Uiso 1 1 calc R . .
H19C H 0.1375 0.2978 0.8484 0.114 Uiso 1 1 calc R . .
C20 C 0.2612(3) 0.0583(2) 0.9142(2) 0.0409(6) Uani 1 1 d . . .
H20 H 0.2809 0.1260 0.9661 0.049 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
O1 0.0625(12) 0.0453(10) 0.0358(9) 0.0006(7) 0.0026(8) 0.0060(8)
C1 0.080(2) 0.0578(19) 0.115(3) 0.0282(19) -0.013(2) -0.0159(17)
C2 0.0684(18) 0.0365(13) 0.0459(15) 0.0031(10) 0.0033(12) 0.0081(12)
C3 0.0417(13) 0.0361(12) 0.0419(13) 0.0010(10) 0.0034(10) 0.0071(10)
C4 0.0568(15) 0.0330(12) 0.0433(14) -0.0071(10) 0.0007(11) 0.0054(11)
C5 0.0506(14) 0.0370(12) 0.0383(13) -0.0019(10) 0.0009(10) 0.0031(10)
C6 0.0720(18) 0.0438(14) 0.0381(14) -0.0019(10) -0.0011(12) 0.0004(12)
C7 0.0611(16) 0.0430(14) 0.0400(14) 0.0023(11) -0.0031(11) 0.0011(12)
C8 0.0621(17) 0.0481(14) 0.0423(14) 0.0105(11) 0.0022(12) 0.0040(12)
C9 0.102(3) 0.0675(19) 0.0440(17) 0.0094(14) 0.0138(16) 0.0123(18)
C10 0.0526(15) 0.0527(14) 0.0368(13) -0.0041(11) 0.0002(11) 0.0087(12)
C11 0.0354(12) 0.0406(12) 0.0381(13) 0.0006(10) 0.0036(9) 0.0052(10)
C12 0.089(3) 0.0511(17) 0.109(3) 0.0119(17) 0.006(2) 0.0250(17)
C13 0.0396(13) 0.0346(12) 0.0429(13) -0.0009(10) 0.0010(10) 0.0044(10)
C14 0.0551(15) 0.0351(12) 0.0400(13) 0.0010(10) 0.0006(11) 0.0039(11)
C15 0.065(2) 0.0579(18) 0.099(3) 0.0136(17) 0.0054(17) -0.0024(15)
C16 0.090(3) 0.071(2) 0.091(3) 0.0141(19) -0.008(2) -0.0167(19)
C17 0.0638(18) 0.0489(15) 0.0600(18) 0.0065(13) -0.0060(14) -0.0066(13)
C18 0.077(2) 0.0650(19) 0.068(2) 0.0073(15) -0.0023(16) 0.0134(16)
C19 0.079(2) 0.0480(17) 0.105(3) 0.0129(17) 0.0132(19) 0.0198(16)
C20 0.0450(14) 0.0364(12) 0.0399(13) -0.0050(10) 0.0016(10) 0.0036(10)
_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 C11 1.369(3) . ?
O1 C10 1.423(3) . ?
C1 C2 1.509(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C12 1.515(4) . ?
C2 C3 1.519(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.388(3) . ?
C3 C11 1.405(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C13 1.395(3) . ?
C5 C6 1.454(4) . ?
C6 C7 1.337(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.515(3) . ?
C7 C14 1.525(3) . ?
C8 C15 1.529(4) . ?
C8 C9 1.529(4) . ?
C8 C18 1.532(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C20 1.396(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C20 1.381(3) . ?
C13 C14 1.516(3) . ?
C14 C17 1.530(4) . ?
C14 C19 1.546(4) . ?
C15 C16 1.597(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.552(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20 0.9300 . ?
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
C11 O1 C10 118.08(19) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C12 111.6(3) . . ?
C1 C2 C3 112.0(2) . . ?
C12 C2 C3 110.8(2) . . ?
C1 C2 H2 107.4 . . ?
C12 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
C4 C3 C11 118.1(2) . . ?
C4 C3 C2 121.0(2) . . ?
C11 C3 C2 121.0(2) . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C13 119.8(2) . . ?
C4 C5 C6 132.4(2) . . ?
C13 C5 C6 107.8(2) . . ?
C7 C6 C5 110.7(2) . . ?
C7 C6 H6 124.6 . . ?
C5 C6 H6 124.6 . . ?
C6 C7 C8 128.0(2) . . ?
C6 C7 C14 110.3(2) . . ?
C8 C7 C14 121.4(2) . . ?
C7 C8 C15 106.8(2) . . ?
C7 C8 C9 110.6(2) . . ?
C15 C8 C9 110.5(3) . . ?
C7 C8 C18 111.0(2) . . ?
C15 C8 C18 110.0(2) . . ?
C9 C8 C18 107.9(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 C20 123.0(2) . . ?
O1 C11 C3 115.6(2) . . ?
C20 C11 C3 121.4(2) . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C20 C13 C5 120.6(2) . . ?
C20 C13 C14 129.7(2) . . ?
C5 C13 C14 109.7(2) . . ?
C13 C14 C7 101.44(18) . . ?
C13 C14 C17 111.9(2) . . ?
C7 C14 C17 109.8(2) . . ?
C13 C14 C19 109.4(2) . . ?
C7 C14 C19 113.7(2) . . ?
C17 C14 C19 110.3(2) . . ?
C8 C15 C16 111.8(3) . . ?
C8 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C8 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 114.4(3) . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C14 C17 C16 109.4(2) . . ?
C14 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
C14 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C20 C11 119.0(2) . . ?
C13 C20 H20 120.5 . . ?
C11 C20 H20 120.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -55.4(4) . . . . ?
C12 C2 C3 C4 70.0(3) . . . . ?
C1 C2 C3 C11 125.9(3) . . . . ?
C12 C2 C3 C11 -108.8(3) . . . . ?
C11 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C5 -179.4(2) . . . . ?
C3 C4 C5 C13 0.7(4) . . . . ?
C3 C4 C5 C6 179.4(3) . . . . ?
C4 C5 C6 C7 -179.4(3) . . . . ?
C13 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 173.0(3) . . . . ?
C5 C6 C7 C14 -0.4(3) . . . . ?
C6 C7 C8 C15 -119.7(3) . . . . ?
C14 C7 C8 C15 53.0(3) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C14 C7 C8 C9 173.3(3) . . . . ?
C6 C7 C8 C18 120.4(3) . . . . ?
C14 C7 C8 C18 -66.9(3) . . . . ?
C10 O1 C11 C20 0.9(3) . . . . ?
C10 O1 C11 C3 -179.0(2) . . . . ?
C4 C3 C11 O1 -179.4(2) . . . . ?
C2 C3 C11 O1 -0.6(3) . . . . ?
C4 C3 C11 C20 0.8(4) . . . . ?
C2 C3 C11 C20 179.5(2) . . . . ?
C4 C5 C13 C20 -0.7(4) . . . . ?
C6 C5 C13 C20 -179.8(2) . . . . ?
C4 C5 C13 C14 -179.8(2) . . . . ?
C6 C5 C13 C14 1.2(3) . . . . ?
C20 C13 C14 C7 179.7(2) . . . . ?
C5 C13 C14 C7 -1.3(3) . . . . ?
C20 C13 C14 C17 62.8(3) . . . . ?
C5 C13 C14 C17 -118.3(2) . . . . ?
C20 C13 C14 C19 -59.8(3) . . . . ?
C5 C13 C14 C19 119.1(3) . . . . ?
C6 C7 C14 C13 1.0(3) . . . . ?
C8 C7 C14 C13 -172.9(2) . . . . ?
C6 C7 C14 C17 119.6(3) . . . . ?
C8 C7 C14 C17 -54.3(3) . . . . ?
C6 C7 C14 C19 -116.3(3) . . . . ?
C8 C7 C14 C19 69.8(3) . . . . ?
C7 C8 C15 C16 -49.1(3) . . . . ?
C9 C8 C15 C16 -169.6(3) . . . . ?
C18 C8 C15 C16 71.4(3) . . . . ?
C8 C15 C16 C17 55.3(4) . . . . ?
C13 C14 C17 C16 161.6(3) . . . . ?
C7 C14 C17 C16 49.8(3) . . . . ?
C19 C14 C17 C16 -76.3(3) . . . . ?
C15 C16 C17 C14 -54.0(4) . . . . ?
C5 C13 C20 C11 0.8(4) . . . . ?
C14 C13 C20 C11 179.7(2) . . . . ?
O1 C11 C20 C13 179.3(2) . . . . ?
C3 C11 C20 C13 -0.8(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.039
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.054


data_shelxl8
_database_code_depnum_ccdc_archive 'CCDC 926021'
#TrackingRef '8.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 O3'
_chemical_formula_weight         286.36
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_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14
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                   8.0057(15)
_cell_length_b                   19.331(4)
_cell_length_c                   9.6263(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.807(11)
_cell_angle_gamma                90.00
_cell_volume                     1482.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.3733
_cell_measurement_theta_max      24.9178
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9830
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11398
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         26.73
_reflns_number_total             3123
_reflns_number_gt                2085
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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^)+(0.0704P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3123
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_iucr_refine_instruction_details 
;
TITL BN266 in P2(1)/n
CELL 0.71073 8.0057 19.3315 9.6263 90.000 95.807 90.000
ZERR 4.00 0.0015 0.0037 0.0016 0.000 0.011 0.000
LATT 1
SYMM -x+1/2, y+1/2, -z+1/2
SFAC C H O
UNIT 72 88 12
L.S. 12
ACTA
BOND $H
CONF
HTAB
SIZE 0.2 0.2 0.2
TEMP -173
MERG 2
FMAP 2
PLAN 10
WGHT 0.070400
FVAR 0.23283
O1 3 0.836892 0.017437 0.804031 11.00000 0.03788 0.03146 =
0.02338 0.00028 0.00271 0.00295
O2 3 0.686415 0.120010 0.780947 11.00000 0.04550 0.02779 =
0.02531 -0.00278 0.00633 0.00241
O3 3 0.634173 0.022044 0.186408 11.00000 0.03866 0.02178 =
0.02363 -0.00010 0.00295 0.00446
C1 1 0.776999 0.027619 0.664812 11.00000 0.02417 0.02645 =
0.02237 0.00420 0.00346 -0.00271
C2 1 0.688237 0.089043 0.651529 11.00000 0.02818 0.02382 =
0.02212 -0.00291 0.00821 -0.00355
C3 1 0.616304 0.112940 0.524774 11.00000 0.02738 0.02151 =
0.02777 0.00116 0.00721 0.00047
AFIX 43
H3 2 0.557106 0.155551 0.515561 11.00000 -1.20000
AFIX 0
C4 1 0.636347 0.070047 0.409915 11.00000 0.02236 0.02143 =
0.02456 0.00153 0.00634 -0.00226
C5 1 0.565702 0.079828 0.259608 11.00000 0.02356 0.02220 =
0.02574 0.00015 0.00603 0.00195
AFIX 13
H5 2 0.441189 0.073725 0.254448 11.00000 -1.20000
AFIX 0
C6 1 0.600626 0.148707 0.191662 11.00000 0.02564 0.02229 =
0.02044 -0.00124 0.00387 -0.00036
C7 1 0.444494 0.188215 0.129054 11.00000 0.02539 0.02363 =
0.02591 0.00055 0.00436 0.00178
C8 1 0.494954 0.250020 0.042600 11.00000 0.03240 0.02873 =
0.03311 0.00364 0.00414 0.00300
AFIX 23
H8A 2 0.526244 0.233136 -0.048345 11.00000 -1.20000
H8B 2 0.397269 0.281256 0.023920 11.00000 -1.20000
AFIX 0
C9 1 0.640972 0.290447 0.115604 11.00000 0.03960 0.02640 =
0.03508 0.00531 0.00611 -0.00407
AFIX 23
H9A 2 0.665378 0.331201 0.058744 11.00000 -1.20000
H9B 2 0.611773 0.307022 0.207408 11.00000 -1.20000
AFIX 0
C10 1 0.762525 0.071097 0.879463 11.00000 0.05759 0.03522 =
0.02797 -0.00116 0.00411 0.01262
AFIX 23
H10A 2 0.676812 0.051333 0.935275 11.00000 -1.20000
H10B 2 0.849411 0.094165 0.943895 11.00000 -1.20000
AFIX 0
C11 1 0.756796 0.173226 0.189377 11.00000 0.02603 0.02354 =
0.02196 -0.00129 0.00500 -0.00014
C12 1 0.912974 0.133138 0.239283 11.00000 0.02507 0.03051 =
0.03029 0.00023 0.00552 -0.00159
AFIX 137
H12A 2 0.955627 0.148950 0.332930 11.00000 -1.50000
H12B 2 0.998659 0.140673 0.175015 11.00000 -1.50000
H12C 2 0.886151 0.083734 0.242344 11.00000 -1.50000
AFIX 0
C13 1 0.793985 0.243984 0.135559 11.00000 0.03078 0.02924 =
0.02904 0.00236 0.00404 -0.00598
AFIX 23
H13A 2 0.841665 0.239096 0.045103 11.00000 -1.20000
H13B 2 0.880003 0.266330 0.201938 11.00000 -1.20000
AFIX 0
C14 1 0.343655 0.213349 0.247071 11.00000 0.03243 0.03017 =
0.03589 0.00112 0.00895 0.00548
AFIX 137
H14A 2 0.411079 0.246518 0.305805 11.00000 -1.50000
H14B 2 0.315475 0.173769 0.303884 11.00000 -1.50000
H14C 2 0.240140 0.235781 0.206746 11.00000 -1.50000
AFIX 0
C15 1 0.332581 0.141611 0.028817 11.00000 0.02857 0.03354 =
0.03051 0.00164 0.00050 0.00157
AFIX 137
H15A 2 0.240533 0.169088 -0.017905 11.00000 -1.50000
H15B 2 0.286320 0.104122 0.081768 11.00000 -1.50000
H15C 2 0.399657 0.121959 -0.041214 11.00000 -1.50000
AFIX 0
C16 1 0.716625 -0.026400 0.283983 11.00000 0.02960 0.02211 =
0.02604 0.00097 0.00362 0.00182
AFIX 23
H16A 2 0.831464 -0.036588 0.260029 11.00000 -1.20000
H16B 2 0.652637 -0.070227 0.283837 11.00000 -1.20000
AFIX 0
C17 1 0.722379 0.008390 0.424058 11.00000 0.02356 0.01918 =
0.02611 0.00108 0.00704 -0.00257
C18 1 0.798292 -0.014452 0.553850 11.00000 0.02257 0.02108 =
0.03023 0.00278 0.00495 0.00224
AFIX 43
H18 2 0.860324 -0.056358 0.563872 11.00000 -1.20000
HKLF 4
END
;
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 0.83689(15) 0.01744(6) 0.80403(11) 0.0309(3) Uani 1 1 d . . .
O2 O 0.68641(15) 0.12001(6) 0.78095(11) 0.0327(3) Uani 1 1 d . . .
O3 O 0.63417(15) 0.02204(6) 0.18641(10) 0.0280(3) Uani 1 1 d . . .
C1 C 0.7770(2) 0.02762(9) 0.66481(16) 0.0243(4) Uani 1 1 d . . .
C2 C 0.6882(2) 0.08904(8) 0.65153(16) 0.0243(4) Uani 1 1 d . . .
C3 C 0.6163(2) 0.11294(9) 0.52477(16) 0.0253(4) Uani 1 1 d . . .
H3 H 0.5571 0.1556 0.5156 0.030 Uiso 1 1 calc R . .
C4 C 0.6363(2) 0.07005(8) 0.40991(16) 0.0225(4) Uani 1 1 d . . .
C5 C 0.5657(2) 0.07983(8) 0.25961(15) 0.0236(4) Uani 1 1 d . . .
H5 H 0.4412 0.0737 0.2544 0.028 Uiso 1 1 calc R . .
C6 C 0.6006(2) 0.14871(8) 0.19166(15) 0.0227(4) Uani 1 1 d . . .
C7 C 0.4445(2) 0.18821(9) 0.12905(16) 0.0249(4) Uani 1 1 d . . .
C8 C 0.4950(2) 0.25002(9) 0.04260(17) 0.0314(4) Uani 1 1 d . . .
H8A H 0.5262 0.2331 -0.0483 0.038 Uiso 1 1 calc R . .
H8B H 0.3973 0.2813 0.0239 0.038 Uiso 1 1 calc R . .
C9 C 0.6410(2) 0.29045(9) 0.11560(19) 0.0335(5) Uani 1 1 d . . .
H9A H 0.6654 0.3312 0.0587 0.040 Uiso 1 1 calc R . .
H9B H 0.6118 0.3070 0.2074 0.040 Uiso 1 1 calc R . .
C10 C 0.7625(3) 0.07110(10) 0.87946(18) 0.0403(5) Uani 1 1 d . . .
H10A H 0.6768 0.0513 0.9353 0.048 Uiso 1 1 calc R . .
H10B H 0.8494 0.0942 0.9439 0.048 Uiso 1 1 calc R . .
C11 C 0.7568(2) 0.17323(8) 0.18938(15) 0.0237(4) Uani 1 1 d . . .
C12 C 0.9130(2) 0.13314(9) 0.23928(17) 0.0284(4) Uani 1 1 d . . .
H12A H 0.9556 0.1490 0.3329 0.043 Uiso 1 1 calc R . .
H12B H 0.9987 0.1407 0.1750 0.043 Uiso 1 1 calc R . .
H12C H 0.8862 0.0837 0.2423 0.043 Uiso 1 1 calc R . .
C13 C 0.7940(2) 0.24398(9) 0.13556(18) 0.0296(4) Uani 1 1 d . . .
H13A H 0.8417 0.2391 0.0451 0.036 Uiso 1 1 calc R . .
H13B H 0.8800 0.2663 0.2019 0.036 Uiso 1 1 calc R . .
C14 C 0.3437(2) 0.21335(9) 0.24707(18) 0.0325(5) Uani 1 1 d . . .
H14A H 0.4111 0.2465 0.3058 0.049 Uiso 1 1 calc R . .
H14B H 0.3155 0.1738 0.3039 0.049 Uiso 1 1 calc R . .
H14C H 0.2401 0.2358 0.2067 0.049 Uiso 1 1 calc R . .
C15 C 0.3326(2) 0.14161(9) 0.02882(17) 0.0310(4) Uani 1 1 d . . .
H15A H 0.2405 0.1691 -0.0179 0.047 Uiso 1 1 calc R . .
H15B H 0.2863 0.1041 0.0818 0.047 Uiso 1 1 calc R . .
H15C H 0.3997 0.1220 -0.0412 0.047 Uiso 1 1 calc R . .
C16 C 0.7166(2) -0.02640(8) 0.28398(15) 0.0259(4) Uani 1 1 d . . .
H16A H 0.8315 -0.0366 0.2600 0.031 Uiso 1 1 calc R . .
H16B H 0.6526 -0.0702 0.2838 0.031 Uiso 1 1 calc R . .
C17 C 0.7224(2) 0.00839(8) 0.42406(16) 0.0226(4) Uani 1 1 d . . .
C18 C 0.7983(2) -0.01445(9) 0.55385(16) 0.0245(4) Uani 1 1 d . . .
H18 H 0.8603 -0.0564 0.5639 0.029 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
O1 0.0379(8) 0.0315(7) 0.0234(6) 0.0003(5) 0.0027(5) 0.0029(6)
O2 0.0455(8) 0.0278(7) 0.0253(6) -0.0028(5) 0.0063(6) 0.0024(6)
O3 0.0387(8) 0.0218(7) 0.0236(6) -0.0001(5) 0.0029(5) 0.0045(5)
C1 0.0242(10) 0.0264(10) 0.0224(9) 0.0042(7) 0.0035(7) -0.0027(8)
C2 0.0282(10) 0.0238(10) 0.0221(9) -0.0029(7) 0.0082(7) -0.0035(8)
C3 0.0274(10) 0.0215(9) 0.0278(9) 0.0012(7) 0.0072(7) 0.0005(8)
C4 0.0224(9) 0.0214(9) 0.0246(9) 0.0015(7) 0.0063(7) -0.0023(7)
C5 0.0236(9) 0.0222(10) 0.0257(9) 0.0002(7) 0.0060(7) 0.0020(7)
C6 0.0256(9) 0.0223(9) 0.0204(8) -0.0012(7) 0.0039(7) -0.0004(8)
C7 0.0254(10) 0.0236(10) 0.0259(9) 0.0005(7) 0.0044(7) 0.0018(8)
C8 0.0324(11) 0.0287(11) 0.0331(10) 0.0036(8) 0.0041(8) 0.0030(9)
C9 0.0396(12) 0.0264(11) 0.0351(10) 0.0053(8) 0.0061(8) -0.0041(9)
C10 0.0576(14) 0.0352(12) 0.0280(10) -0.0012(9) 0.0041(9) 0.0126(10)
C11 0.0260(10) 0.0235(10) 0.0220(8) -0.0013(7) 0.0050(7) -0.0001(8)
C12 0.0251(10) 0.0305(10) 0.0303(9) 0.0002(8) 0.0055(8) -0.0016(8)
C13 0.0308(10) 0.0292(11) 0.0290(9) 0.0024(8) 0.0040(8) -0.0060(8)
C14 0.0324(11) 0.0302(11) 0.0359(10) 0.0011(8) 0.0090(8) 0.0055(8)
C15 0.0286(10) 0.0335(11) 0.0305(9) 0.0016(8) 0.0005(8) 0.0016(9)
C16 0.0296(10) 0.0221(10) 0.0260(9) 0.0010(7) 0.0036(7) 0.0018(8)
C17 0.0236(10) 0.0192(9) 0.0261(9) 0.0011(7) 0.0070(7) -0.0026(7)
C18 0.0226(10) 0.0211(9) 0.0302(9) 0.0028(7) 0.0049(7) 0.0022(7)
_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 C1 1.3909(18) . ?
O1 C10 1.4301(19) . ?
O2 C2 1.3836(18) . ?
O2 C10 1.431(2) . ?
O3 C16 1.4386(18) . ?
O3 C5 1.4570(17) . ?
C1 C18 1.367(2) . ?
C1 C2 1.383(2) . ?
C2 C3 1.375(2) . ?
C3 C4 1.404(2) . ?
C3 H3 0.9500 . ?
C4 C17 1.376(2) . ?
C4 C5 1.511(2) . ?
C5 C6 1.522(2) . ?
C5 H5 1.0000 . ?
C6 C11 1.339(2) . ?
C6 C7 1.535(2) . ?
C7 C8 1.533(2) . ?
C7 C14 1.538(2) . ?
C7 C15 1.540(2) . ?
C8 C9 1.518(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C13 1.515(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C13 1.503(2) . ?
C11 C12 1.508(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.503(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.404(2) . ?
C18 H18 0.9500 . ?
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
C1 O1 C10 105.42(12) . . ?
C2 O2 C10 105.56(12) . . ?
C16 O3 C5 110.70(11) . . ?
C18 C1 C2 122.83(15) . . ?
C18 C1 O1 127.64(15) . . ?
C2 C1 O1 109.53(14) . . ?
C3 C2 C1 122.38(15) . . ?
C3 C2 O2 127.73(15) . . ?
C1 C2 O2 109.90(14) . . ?
C2 C3 C4 115.42(15) . . ?
C2 C3 H3 122.3 . . ?
C4 C3 H3 122.3 . . ?
C17 C4 C3 121.96(15) . . ?
C17 C4 C5 109.76(14) . . ?
C3 C4 C5 128.21(15) . . ?
O3 C5 C4 104.15(12) . . ?
O3 C5 C6 111.62(11) . . ?
C4 C5 C6 116.99(14) . . ?
O3 C5 H5 107.9 . . ?
C4 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
C11 C6 C5 121.94(15) . . ?
C11 C6 C7 122.81(15) . . ?
C5 C6 C7 115.24(14) . . ?
C8 C7 C6 110.61(13) . . ?
C8 C7 C14 109.98(14) . . ?
C6 C7 C14 109.55(13) . . ?
C8 C7 C15 106.52(13) . . ?
C6 C7 C15 110.73(13) . . ?
C14 C7 C15 109.40(14) . . ?
C9 C8 C7 112.50(14) . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C13 C9 C8 109.16(15) . . ?
C13 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C13 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
O2 C10 O1 108.30(12) . . ?
O2 C10 H10A 110.0 . . ?
O1 C10 H10A 110.0 . . ?
O2 C10 H10B 110.0 . . ?
O1 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C6 C11 C13 123.06(15) . . ?
C6 C11 C12 123.94(15) . . ?
C13 C11 C12 113.00(14) . . ?
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 C9 113.41(14) . . ?
C11 C13 H13A 108.9 . . ?
C9 C13 H13A 108.9 . . ?
C11 C13 H13B 108.9 . . ?
C9 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 C17 105.35(13) . . ?
O3 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
O3 C16 H16B 110.7 . . ?
C17 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C4 C17 C18 121.84(15) . . ?
C4 C17 C16 109.21(14) . . ?
C18 C17 C16 128.95(15) . . ?
C1 C18 C17 115.55(15) . . ?
C1 C18 H18 122.2 . . ?
C17 C18 H18 122.2 . . ?
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 C18 -172.71(17) . . . . ?
C10 O1 C1 C2 7.32(17) . . . . ?
C18 C1 C2 C3 -0.9(3) . . . . ?
O1 C1 C2 C3 179.09(14) . . . . ?
C18 C1 C2 O2 179.44(15) . . . . ?
O1 C1 C2 O2 -0.59(18) . . . . ?
C10 O2 C2 C3 173.94(17) . . . . ?
C10 O2 C2 C1 -6.40(18) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
O2 C2 C3 C4 -179.21(14) . . . . ?
C2 C3 C4 C17 0.0(2) . . . . ?
C2 C3 C4 C5 176.69(15) . . . . ?
C16 O3 C5 C4 9.11(16) . . . . ?
C16 O3 C5 C6 136.22(14) . . . . ?
C17 C4 C5 O3 -5.93(16) . . . . ?
C3 C4 C5 O3 177.01(15) . . . . ?
C17 C4 C5 C6 -129.63(15) . . . . ?
C3 C4 C5 C6 53.3(2) . . . . ?
O3 C5 C6 C11 -65.35(19) . . . . ?
C4 C5 C6 C11 54.5(2) . . . . ?
O3 C5 C6 C7 115.78(14) . . . . ?
C4 C5 C6 C7 -124.43(15) . . . . ?
C11 C6 C7 C8 10.7(2) . . . . ?
C5 C6 C7 C8 -170.43(13) . . . . ?
C11 C6 C7 C14 -110.68(17) . . . . ?
C5 C6 C7 C14 68.18(17) . . . . ?
C11 C6 C7 C15 128.56(16) . . . . ?
C5 C6 C7 C15 -52.58(17) . . . . ?
C6 C7 C8 C9 -44.33(18) . . . . ?
C14 C7 C8 C9 76.81(18) . . . . ?
C15 C7 C8 C9 -164.73(14) . . . . ?
C7 C8 C9 C13 62.55(17) . . . . ?
C2 O2 C10 O1 10.90(18) . . . . ?
C1 O1 C10 O2 -11.23(18) . . . . ?
C5 C6 C11 C13 -173.90(13) . . . . ?
C7 C6 C11 C13 4.9(2) . . . . ?
C5 C6 C11 C12 6.4(2) . . . . ?
C7 C6 C11 C12 -174.77(14) . . . . ?
C6 C11 C13 C9 13.2(2) . . . . ?
C12 C11 C13 C9 -167.11(14) . . . . ?
C8 C9 C13 C11 -45.33(19) . . . . ?
C5 O3 C16 C17 -8.77(16) . . . . ?
C3 C4 C17 C18 -1.4(2) . . . . ?
C5 C4 C17 C18 -178.70(14) . . . . ?
C3 C4 C17 C16 178.03(14) . . . . ?
C5 C4 C17 C16 0.75(18) . . . . ?
O3 C16 C17 C4 4.82(17) . . . . ?
O3 C16 C17 C18 -175.77(15) . . . . ?
C2 C1 C18 C17 -0.6(2) . . . . ?
O1 C1 C18 C17 179.47(14) . . . . ?
C4 C17 C18 C1 1.7(2) . . . . ?
C16 C17 C18 C1 -177.65(15) . . . . ?
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.73
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.047