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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global

data_NABA

_audit_creation_method           SHELXL-97
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H30 O3'
_chemical_formula_weight         318.44
_chemical_melting_point          ?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_absolute_configuration rm
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'x, y, z'
'-x, y+1/2, -z+1/2'

_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.77744(12)
_cell_length_b                   14.0740(3)
_cell_length_c                   19.0348(4)
_cell_measurement_reflns_used    3402
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9145
_cell_measurement_theta_min      3.1374
_cell_volume                     1815.64(6)
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.8435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_F_000             696
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_special_details           ?
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
1 omega 17.00 65.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 0.0000 37.0000 -180.0000 48
2 omega -76.00 21.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -42.5000 0.0000 -150.0000 97
3 omega -107.00 -81.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -42.5000 179.0000 -180.0000 26
4 omega -8.00 18.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 55.1592 -77.0000 120.0000 26
5 omega -1.00 25.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 55.1592 -37.0000 -60.0000 26
6 omega 41.00 78.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 55.1592 -77.0000 120.0000 37
7 omega 90.00 116.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.3184 -50.0000 -30.0000 26
8 omega 82.00 143.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.3184 -25.0000 30.0000 61
9 omega 90.00 132.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.3184 -50.0000 0.0000 42
10 omega 87.00 125.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.3184 -50.0000 150.0000 38
11 omega 82.00 118.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.3184 -25.0000 -180.0000 36
12 omega 47.00 93.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.3184 -95.0000 -143.0000 46
13 omega 127.00 174.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.3184 111.0000 -60.0000 47
14 omega 82.00 107.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.3184 -25.0000 90.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0413634
_diffrn_orient_matrix_UB_12      0.1076944
_diffrn_orient_matrix_UB_13      0.0015617
_diffrn_orient_matrix_UB_21      -0.084332
_diffrn_orient_matrix_UB_22      -0.0093199
_diffrn_orient_matrix_UB_23      0.0749638
_diffrn_orient_matrix_UB_31      0.206708
_diffrn_orient_matrix_UB_32      0.0176088
_diffrn_orient_matrix_UB_33      0.0305966
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0072
_diffrn_reflns_av_sigmaI/netI    0.0092
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4323
_diffrn_reflns_theta_full        72.06
_diffrn_reflns_theta_max         72.06
_diffrn_reflns_theta_min         3.91
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2627
_reflns_number_total             2870
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material  
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0466
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1336
_refine_ls_weighting_details     
;
calc w=1/[\s^2^(Fo^2^)+(0.0936P)^2^+0.0925P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_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.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C8 C 0.8208(3) 0.86076(13) 0.19630(9) 0.0519(4) Uani 1 1 d . . .
H8 H 0.7303 0.8368 0.1603 0.062 Uiso 1 1 calc R . .
C11 C 0.7581(3) 0.96349(14) 0.21428(10) 0.0615(5) Uani 1 1 d . . .
H11 H 0.8557 0.9900 0.2468 0.074 Uiso 1 1 calc R . .
O1 O 0.3118(3) 0.90729(12) 0.41715(7) 0.0735(4) Uani 1 1 d . . .
C14 C 0.5621(3) 0.90438(13) 0.31937(9) 0.0516(4) Uani 1 1 d . . .
C7 C 0.8063(3) 0.79430(15) 0.26037(9) 0.0567(4) Uani 1 1 d . . .
H7A H 0.8240 0.7293 0.2447 0.068 Uiso 1 1 calc R . .
H7B H 0.9130 0.8091 0.2926 0.068 Uiso 1 1 calc R . .
C9 C 0.6095(3) 0.80178(13) 0.30000(9) 0.0547(4) Uani 1 1 d . . .
H9A H 0.5045 0.7765 0.2708 0.066 Uiso 1 1 calc R . .
H9B H 0.6161 0.7638 0.3424 0.066 Uiso 1 1 calc R . .
C6 C 1.0296(3) 0.86155(18) 0.16473(10) 0.0663(5) Uani 1 1 d . . .
H6 H 1.1174 0.8886 0.2004 0.080 Uiso 1 1 calc R . .
C10 C 0.5609(3) 0.96281(13) 0.25068(11) 0.0564(4) Uani 1 1 d . . .
H10 H 0.4693 0.9305 0.2188 0.068 Uiso 1 1 calc R . .
C19 C 0.2115(3) 0.83059(15) 0.43587(11) 0.0641(5) Uani 1 1 d . . .
C2 C 1.1113(3) 0.7641(2) 0.14601(12) 0.0846(8) Uani 1 1 d . . .
H2B H 1.2498 0.7703 0.1339 0.101 Uiso 1 1 calc R . .
H2A H 1.1022 0.7230 0.1868 0.101 Uiso 1 1 calc R . .
O3 O 1.0218(3) 0.75067(19) -0.03739(8) 0.1032(8) Uani 1 1 d . . .
C3 C 0.9934(3) 0.7814(2) 0.02164(11) 0.0773(7) Uani 1 1 d . . .
C5 C 1.0430(4) 0.9267(2) 0.09935(12) 0.0794(7) Uani 1 1 d . . .
H5 H 1.1831 0.9336 0.0876 0.095 Uiso 1 1 calc R . .
O2 O 0.1664(4) 0.76989(14) 0.39564(10) 0.1042(8) Uani 1 1 d . . .
C18 C 0.7067(3) 0.94258(18) 0.37441(11) 0.0698(6) Uani 1 1 d . . .
H18A H 0.6929 0.9069 0.4171 0.105 Uiso 1 1 calc R . .
H18C H 0.6785 1.0083 0.3834 0.105 Uiso 1 1 calc R . .
H18B H 0.8392 0.9365 0.3572 0.105 Uiso 1 1 calc R . .
C15 C 0.3487(3) 0.92419(15) 0.34289(11) 0.0609(5) Uani 1 1 d . . .
H15 H 0.2574 0.8860 0.3147 0.073 Uiso 1 1 calc R . .
C1 C 1.0027(4) 0.7178(2) 0.08498(12) 0.0827(7) Uani 1 1 d . . .
H1B H 1.0691 0.6591 0.0724 0.099 Uiso 1 1 calc R . .
H1A H 0.8697 0.7019 0.0996 0.099 Uiso 1 1 calc R . .
C4 C 0.9413(4) 0.8816(2) 0.03603(11) 0.0807(7) Uani 1 1 d . . .
H4A H 0.7998 0.8855 0.0430 0.097 Uiso 1 1 calc R . .
H4B H 0.9730 0.9190 -0.0053 0.097 Uiso 1 1 calc R . .
C13 C 0.9625(6) 1.0257(2) 0.11412(16) 0.1013(10) Uani 1 1 d . . .
H13A H 0.9564 1.0609 0.0704 0.122 Uiso 1 1 calc R . .
H13B H 1.0530 1.0588 0.1452 0.122 Uiso 1 1 calc R . .
C17 C 0.4614(5) 1.05713(16) 0.27133(15) 0.0832(7) Uani 1 1 d . . .
H17B H 0.5577 1.1020 0.2893 0.100 Uiso 1 1 calc R . .
H17A H 0.3947 1.0853 0.2313 0.100 Uiso 1 1 calc R . .
C16 C 0.3130(4) 1.02949(16) 0.32858(14) 0.0791(6) Uani 1 1 d . . .
H16B H 0.3347 1.0667 0.3708 0.095 Uiso 1 1 calc R . .
H16A H 0.1789 1.0399 0.3125 0.095 Uiso 1 1 calc R . .
C12 C 0.7584(5) 1.02454(17) 0.14753(14) 0.0860(8) Uani 1 1 d . . .
H12A H 0.6635 0.9993 0.1143 0.103 Uiso 1 1 calc R . .
H12B H 0.7193 1.0889 0.1592 0.103 Uiso 1 1 calc R . .
C20 C 0.1681(5) 0.8289(3) 0.51298(13) 0.0992(10) Uani 1 1 d . . .
H20C H 0.0978 0.8855 0.5258 0.149 Uiso 1 1 calc R . .
H20B H 0.2897 0.8258 0.5388 0.149 Uiso 1 1 calc R . .
H20A H 0.0890 0.7743 0.5238 0.149 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
C8 0.0489(8) 0.0656(10) 0.0411(7) 0.0054(8) -0.0037(7) -0.0103(8)
C11 0.0680(11) 0.0567(10) 0.0599(10) 0.0060(8) 0.0006(9) -0.0180(9)
O1 0.0723(9) 0.0913(10) 0.0568(7) -0.0199(7) 0.0102(7) -0.0227(8)
C14 0.0546(9) 0.0527(9) 0.0474(9) -0.0056(7) -0.0002(7) -0.0084(8)
C7 0.0641(10) 0.0625(9) 0.0434(8) 0.0047(8) 0.0021(8) 0.0038(9)
C9 0.0707(11) 0.0503(9) 0.0430(8) 0.0041(7) 0.0076(8) -0.0051(8)
C6 0.0474(9) 0.1049(16) 0.0464(9) 0.0062(10) -0.0031(8) -0.0111(10)
C10 0.0602(10) 0.0498(9) 0.0593(10) 0.0039(8) -0.0051(9) -0.0066(8)
C19 0.0570(10) 0.0729(11) 0.0625(11) -0.0009(10) -0.0057(9) -0.0086(9)
C2 0.0593(11) 0.141(2) 0.0538(10) 0.0184(13) 0.0081(9) 0.0236(14)
O3 0.0755(10) 0.180(2) 0.0541(9) -0.0117(11) 0.0011(8) 0.0114(13)
C3 0.0523(9) 0.130(2) 0.0494(10) 0.0022(12) 0.0033(8) -0.0027(13)
C5 0.0638(12) 0.1115(19) 0.0628(12) 0.0178(12) 0.0131(10) -0.0257(13)
O2 0.157(2) 0.0787(11) 0.0770(10) 0.0083(9) -0.0141(13) -0.0354(13)
C18 0.0617(11) 0.0877(14) 0.0602(11) -0.0180(10) -0.0036(10) -0.0114(11)
C15 0.0588(10) 0.0691(12) 0.0550(10) -0.0115(9) 0.0013(9) -0.0096(9)
C1 0.0800(15) 0.1019(17) 0.0663(13) 0.0046(13) 0.0150(12) 0.0152(15)
C4 0.0808(14) 0.1134(19) 0.0478(10) 0.0240(11) 0.0042(10) -0.0070(15)
C13 0.116(2) 0.0917(18) 0.0966(19) 0.0236(16) 0.0292(19) -0.0340(18)
C17 0.0900(16) 0.0565(11) 0.1032(18) 0.0043(12) 0.0057(15) 0.0033(11)
C16 0.0707(13) 0.0726(13) 0.0940(16) -0.0125(12) 0.0070(13) 0.0079(11)
C12 0.104(2) 0.0651(12) 0.0884(16) 0.0255(12) 0.0142(16) -0.0115(13)
C20 0.0920(18) 0.139(3) 0.0671(14) -0.0050(15) 0.0135(14) -0.0370(18)

_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
C8 C11 1.545(3) . ?
C8 C7 1.540(2) . ?
C8 C6 1.537(3) . ?
C11 C10 1.506(3) . ?
C11 C12 1.534(3) . ?
O1 C19 1.325(3) . ?
O1 C15 1.455(2) . ?
C14 C9 1.524(3) . ?
C14 C10 1.545(3) . ?
C14 C18 1.532(3) . ?
C14 C15 1.540(3) . ?
C7 C9 1.536(3) . ?
C6 C2 1.522(4) . ?
C6 C5 1.548(3) . ?
C10 C17 1.540(3) . ?
C19 O2 1.187(3) . ?
C19 C20 1.497(3) . ?
C2 C1 1.522(4) . ?
O3 C3 1.219(3) . ?
C3 C1 1.503(3) . ?
C3 C4 1.480(4) . ?
C5 C4 1.526(3) . ?
C5 C13 1.523(4) . ?
C15 C16 1.526(3) . ?
C13 C12 1.523(4) . ?
C17 C16 1.533(4) . ?

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
C8 C6 C5 111.89(18) . . ?
C11 C10 C14 112.84(16) . . ?
C11 C10 C17 120.06(17) . . ?
O1 C19 C20 112.2(2) . . ?
O1 C15 C14 114.47(18) . . ?
O1 C15 C16 107.76(18) . . ?
C14 C9 C7 111.51(15) . . ?
C7 C8 C11 112.04(15) . . ?
C9 C14 C10 107.50(14) . . ?
C9 C14 C18 111.30(18) . . ?
C9 C14 C15 116.08(16) . . ?
C9 C7 C8 113.74(16) . . ?
C6 C8 C11 109.44(16) . . ?
C6 C8 C7 111.88(16) . . ?
C10 C11 C8 109.88(14) . . ?
C10 C11 C12 112.7(2) . . ?
C19 O1 C15 118.87(16) . . ?
C2 C6 C8 114.84(19) . . ?
C2 C6 C5 108.90(18) . . ?
O3 C3 C1 121.4(3) . . ?
O3 C3 C4 123.1(3) . . ?
C3 C1 C2 112.2(2) . . ?
C3 C4 C5 115.8(2) . . ?
C5 C13 C12 113.1(2) . . ?
O2 C19 O1 123.0(2) . . ?
O2 C19 C20 124.8(2) . . ?
C18 C14 C10 113.30(16) . . ?
C18 C14 C15 109.77(16) . . ?
C15 C14 C10 98.31(16) . . ?
C15 C16 C17 105.62(19) . . ?
C1 C2 C6 112.86(19) . . ?
C4 C3 C1 115.4(2) . . ?
C4 C5 C6 111.2(2) . . ?
C13 C5 C6 111.9(2) . . ?
C13 C5 C4 111.3(3) . . ?
C13 C12 C11 110.7(2) . . ?
C17 C10 C14 104.20(17) . . ?
C16 C15 C14 105.84(18) . . ?
C16 C17 C10 104.48(18) . . ?
C12 C11 C8 109.90(17) . . ?
_database_code_depnum_ccdc_archive 'CCDC 888376'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global

# Attachment 'dbr34.cif'


data_test
#TrackingRef 'dbr34.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H28 O2'
_chemical_formula_weight         288.41
_chemical_absolute_configuration rm

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

_cell_length_a                   7.9253(18)
_cell_length_b                   8.4074(17)
_cell_length_c                   25.074(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1670.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1490
_cell_measurement_theta_min      2.9113
_cell_measurement_theta_max      26.2903

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4819
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         26.35
_reflns_number_total             3097
_reflns_number_gt                2166
_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^)+(0.0575P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_number_reflns         3097
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
C12 C 0.5104(3) 0.2607(3) 0.87317(12) 0.0653(8) Uani 1 1 d . . .
H12A H 0.5590 0.1913 0.8464 0.078 Uiso 1 1 calc R . .
H12B H 0.5518 0.3675 0.8666 0.078 Uiso 1 1 calc R . .
O2 O 0.6456(3) 0.0064(2) 1.02626(9) 0.0889(7) Uani 1 1 d . . .
C13 C 0.5710(3) 0.2066(3) 0.92831(12) 0.0646(8) Uani 1 1 d . . .
H13A H 0.6932 0.1993 0.9284 0.078 Uiso 1 1 calc R . .
H13B H 0.5381 0.2846 0.9549 0.078 Uiso 1 1 calc R . .
C9 C 0.3211(4) 0.1948(4) 0.76725(12) 0.0884(10) Uani 1 1 d . . .
H9A H 0.2841 0.0890 0.7756 0.133 Uiso 1 1 calc R . .
H9B H 0.4421 0.1974 0.7659 0.133 Uiso 1 1 calc R . .
H9C H 0.2762 0.2260 0.7333 0.133 Uiso 1 1 calc R . .
C10 C 0.3178(3) 0.2602(3) 0.86695(10) 0.0465(6) Uani 1 1 d . . .
H10 H 0.2745 0.3407 0.8917 0.056 Uiso 1 1 calc R . .
C11 C 0.2394(3) 0.0995(3) 0.88459(10) 0.0460(6) Uani 1 1 d . . .
H11 H 0.2775 0.0164 0.8600 0.055 Uiso 1 1 calc R . .
C5 C 0.0643(3) 0.3169(3) 0.80932(11) 0.0562(7) Uani 1 1 d . . .
H5 H 0.0307 0.3332 0.7721 0.067 Uiso 1 1 calc R . .
C15 C 0.3034(3) 0.0598(3) 0.93999(11) 0.0488(6) Uani 1 1 d . . .
H15 H 0.2739 0.1512 0.9624 0.059 Uiso 1 1 calc R . .
C14 C 0.4960(3) 0.0460(3) 0.94258(11) 0.0521(6) Uani 1 1 d . . .
C8 C 0.0487(3) 0.1079(3) 0.88227(12) 0.0583(7) Uani 1 1 d . . .
H8A H 0.0088 0.1825 0.9089 0.070 Uiso 1 1 calc R . .
H8B H 0.0022 0.0042 0.8907 0.070 Uiso 1 1 calc R . .
C4 C -0.0099(4) 0.4548(3) 0.84191(12) 0.0667(8) Uani 1 1 d . . .
H4A H -0.1286 0.4647 0.8331 0.080 Uiso 1 1 calc R . .
H4B H -0.0027 0.4275 0.8794 0.080 Uiso 1 1 calc R . .
C6 C 0.2582(3) 0.3106(3) 0.81060(11) 0.0563(7) Uani 1 1 d . . .
C7 C -0.0137(3) 0.1596(3) 0.82760(12) 0.0636(8) Uani 1 1 d . . .
H7A H -0.1355 0.1708 0.8287 0.076 Uiso 1 1 calc R . .
H7B H 0.0131 0.0775 0.8018 0.076 Uiso 1 1 calc R . .
C16 C 0.5679(3) -0.0877(3) 0.90714(12) 0.0742(9) Uani 1 1 d . . .
H16A H 0.6885 -0.0904 0.9106 0.111 Uiso 1 1 calc R . .
H16B H 0.5385 -0.0678 0.8706 0.111 Uiso 1 1 calc R . .
H16C H 0.5216 -0.1880 0.9181 0.111 Uiso 1 1 calc R . .
C17 C 0.2410(3) -0.0872(3) 0.97024(13) 0.0674(8) Uani 1 1 d . . .
H17A H 0.1264 -0.0724 0.9829 0.081 Uiso 1 1 calc R . .
H17B H 0.2456 -0.1814 0.9480 0.081 Uiso 1 1 calc R . .
C1 C 0.0714(5) 0.6121(4) 0.83406(13) 0.0822(10) Uani 1 1 d . . .
O1 O -0.0080(4) 0.7344(3) 0.83193(12) 0.1284(11) Uani 1 1 d . . .
C19 C 0.5211(4) -0.0118(3) 0.99938(12) 0.0638(7) Uani 1 1 d . . .
C3 C 0.3213(4) 0.4763(4) 0.79500(14) 0.0845(10) Uani 1 1 d . . .
H3A H 0.4437 0.4757 0.7956 0.101 Uiso 1 1 calc R . .
H3B H 0.2863 0.4981 0.7587 0.101 Uiso 1 1 calc R . .
C2 C 0.2592(5) 0.6107(3) 0.83054(15) 0.0942(12) Uani 1 1 d . . .
H2A H 0.3065 0.5983 0.8660 0.113 Uiso 1 1 calc R . .
H2B H 0.2981 0.7116 0.8163 0.113 Uiso 1 1 calc R . .
C18 C 0.3641(4) -0.0993(4) 1.01646(14) 0.0825(9) Uani 1 1 d . . .
H18A H 0.3166 -0.0510 1.0482 0.099 Uiso 1 1 calc R . .
H18B H 0.3898 -0.2097 1.0241 0.099 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
C12 0.0401(14) 0.0786(18) 0.077(2) 0.0107(16) 0.0034(14) -0.0125(14)
O2 0.0884(14) 0.0965(16) 0.0817(16) -0.0019(13) -0.0316(13) -0.0046(12)
C13 0.0406(14) 0.0718(19) 0.081(2) 0.0012(16) -0.0070(14) -0.0104(13)
C9 0.075(2) 0.127(3) 0.063(2) -0.016(2) 0.0076(17) 0.022(2)
C10 0.0385(12) 0.0464(12) 0.0546(15) -0.0049(12) 0.0062(11) -0.0035(11)
C11 0.0367(11) 0.0425(12) 0.0589(16) -0.0083(12) 0.0036(11) 0.0003(11)
C5 0.0554(15) 0.0597(15) 0.0537(17) -0.0069(14) -0.0080(13) 0.0102(13)
C15 0.0421(12) 0.0411(13) 0.0631(17) -0.0040(12) 0.0026(12) -0.0039(11)
C14 0.0438(12) 0.0533(14) 0.0591(16) -0.0039(13) -0.0034(12) -0.0002(12)
C8 0.0391(14) 0.0504(14) 0.085(2) 0.0006(15) 0.0000(13) -0.0067(11)
C4 0.0692(17) 0.0609(17) 0.0700(19) -0.0032(15) -0.0035(16) 0.0147(15)
C6 0.0527(14) 0.0669(16) 0.0493(16) -0.0011(14) 0.0051(12) 0.0013(14)
C7 0.0410(14) 0.0640(17) 0.086(2) -0.0117(16) -0.0117(15) 0.0012(13)
C16 0.0547(15) 0.083(2) 0.085(2) -0.0116(18) -0.0092(15) 0.0178(15)
C17 0.0605(15) 0.0553(16) 0.086(2) 0.0105(16) -0.0015(16) -0.0091(14)
C1 0.120(3) 0.056(2) 0.070(2) -0.0065(17) -0.029(2) 0.013(2)
O1 0.190(3) 0.0583(14) 0.137(2) -0.0136(14) -0.054(2) 0.0374(17)
C19 0.0637(16) 0.0558(15) 0.0720(19) -0.0046(14) -0.0129(15) 0.0051(14)
C3 0.078(2) 0.099(2) 0.077(2) 0.035(2) 0.0009(18) -0.019(2)
C2 0.129(3) 0.0547(18) 0.099(3) 0.019(2) -0.022(2) -0.024(2)
C18 0.083(2) 0.079(2) 0.086(2) 0.0168(19) -0.0058(18) -0.0014(18)

_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
C12 C13 1.533(4) . ?
C12 C10 1.534(3) . ?
O2 C19 1.204(3) . ?
C13 C14 1.518(3) . ?
C9 C6 1.542(4) . ?
C10 C6 1.549(4) . ?
C10 C11 1.551(3) . ?
C11 C8 1.514(3) . ?
C11 C15 1.516(4) . ?
C5 C7 1.530(4) . ?
C5 C4 1.536(4) . ?
C5 C6 1.538(3) . ?
C15 C17 1.532(3) . ?
C15 C14 1.532(3) . ?
C14 C19 1.518(4) . ?
C14 C16 1.542(3) . ?
C8 C7 1.521(4) . ?
C4 C1 1.484(4) . ?
C6 C3 1.531(4) . ?
C17 C18 1.518(4) . ?
C1 O1 1.207(3) . ?
C1 C2 1.491(4) . ?
C19 C18 1.508(4) . ?
C3 C2 1.521(5) . ?

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
C13 C12 C10 113.8(2) . . ?
C14 C13 C12 110.7(2) . . ?
C12 C10 C6 113.3(2) . . ?
C12 C10 C11 111.8(2) . . ?
C6 C10 C11 112.1(2) . . ?
C8 C11 C15 112.3(2) . . ?
C8 C11 C10 110.4(2) . . ?
C15 C11 C10 108.59(18) . . ?
C7 C5 C4 109.8(2) . . ?
C7 C5 C6 111.6(2) . . ?
C4 C5 C6 113.4(2) . . ?
C11 C15 C17 121.5(2) . . ?
C11 C15 C14 112.9(2) . . ?
C17 C15 C14 103.9(2) . . ?
C19 C14 C13 117.0(2) . . ?
C19 C14 C15 101.2(2) . . ?
C13 C14 C15 108.2(2) . . ?
C19 C14 C16 105.0(2) . . ?
C13 C14 C16 111.5(2) . . ?
C15 C14 C16 113.5(2) . . ?
C11 C8 C7 111.9(2) . . ?
C1 C4 C5 115.8(3) . . ?
C3 C6 C5 106.9(2) . . ?
C3 C6 C9 106.8(3) . . ?
C5 C6 C9 109.3(2) . . ?
C3 C6 C10 112.5(2) . . ?
C5 C6 C10 109.4(2) . . ?
C9 C6 C10 111.8(2) . . ?
C8 C7 C5 112.7(2) . . ?
C18 C17 C15 103.0(2) . . ?
O1 C1 C4 122.6(4) . . ?
O1 C1 C2 121.6(3) . . ?
C4 C1 C2 115.8(3) . . ?
O2 C19 C18 125.4(3) . . ?
O2 C19 C14 126.3(3) . . ?
C18 C19 C14 108.3(2) . . ?
C2 C3 C6 114.9(3) . . ?
C1 C2 C3 111.3(3) . . ?
C19 C18 C17 106.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.35
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.032


_database_code_depnum_ccdc_archive 'CCDC 888377'