# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# 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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# 
#  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.
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data_global


data_dm12486
#TrackingRef 'dm12486.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H30 O3'
_chemical_formula_weight         270.40

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

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

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

_cell_length_a                   33.5085(13)
_cell_length_b                   6.1892(2)
_cell_length_c                   8.0369(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1666.78(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    5737
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      68.92

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.078
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8709
_exptl_absorpt_correction_T_max  0.9045
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8764
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.28
_diffrn_reflns_theta_max         64.98
_reflns_number_total             2728
_reflns_number_gt                2643
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of 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^)+(0.0611P)^2^+1.3914P] 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   0.1(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2728
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12079(6) 0.1964(4) 0.3534(2) 0.0332(5) Uani 1 1 d . . .
H1 H 0.1102 0.3148 0.3275 0.050 Uiso 1 1 calc R . .
O2 O 0.09331(6) -0.0672(4) 1.1156(2) 0.0348(5) Uani 1 1 d . . .
H2 H 0.0978 -0.0015 1.2051 0.052 Uiso 1 1 calc R . .
C1 C 0.20678(8) 0.0572(6) 0.7781(4) 0.0346(7) Uani 1 1 d . . .
H1A H 0.2023 -0.0872 0.7428 0.041 Uiso 1 1 calc R . .
C2 C 0.23284(9) 0.1923(7) 0.6685(4) 0.0426(8) Uani 1 1 d . . .
H2A H 0.2587 0.1174 0.6530 0.051 Uiso 1 1 calc R . .
H2B H 0.2383 0.3313 0.7250 0.051 Uiso 1 1 calc R . .
C3 C 0.21450(8) 0.2389(6) 0.4962(4) 0.0370(7) Uani 1 1 d . . .
H3A H 0.2334 0.3279 0.4309 0.044 Uiso 1 1 calc R . .
H3B H 0.2107 0.1006 0.4363 0.044 Uiso 1 1 calc R . .
C4 C 0.17495(9) 0.3548(5) 0.5066(4) 0.0315(6) Uani 1 1 d . . .
C5 C 0.13790(8) 0.2126(5) 0.5171(3) 0.0282(6) Uani 1 1 d . . .
H5 H 0.1471 0.0645 0.5491 0.034 Uiso 1 1 calc R . .
C6 C 0.10692(8) 0.2825(5) 0.6461(4) 0.0303(6) Uani 1 1 d . . .
H6A H 0.0904 0.3987 0.5967 0.036 Uiso 1 1 calc R . .
H6B H 0.1212 0.3451 0.7425 0.036 Uiso 1 1 calc R . .
C7 C 0.10180(8) -0.0596(5) 0.8185(3) 0.0312(6) Uani 1 1 d . . .
H7A H 0.0841 -0.1842 0.8408 0.037 Uiso 1 1 calc R . .
H7B H 0.1246 -0.1138 0.7524 0.037 Uiso 1 1 calc R . .
C8 C 0.11789(8) 0.0221(5) 0.9855(3) 0.0289(6) Uani 1 1 d . . .
H8 H 0.1151 0.1829 0.9880 0.035 Uiso 1 1 calc R . .
C9 C 0.16182(8) -0.0347(5) 1.0143(4) 0.0335(6) Uani 1 1 d . . .
H9A H 0.1679 -0.0257 1.1347 0.040 Uiso 1 1 calc R . .
H9B H 0.1668 -0.1851 0.9778 0.040 Uiso 1 1 calc R . .
C10 C 0.18914(8) 0.1162(5) 0.9201(4) 0.0322(7) Uani 1 1 d . . .
C11 C 0.07865(8) 0.1036(5) 0.7108(3) 0.0319(7) Uani 1 1 d . . .
C12 C 0.04549(9) 0.2119(7) 0.8120(4) 0.0490(9) Uani 1 1 d . . .
H12A H 0.0294 0.3034 0.7386 0.073 Uiso 1 1 calc R . .
H12B H 0.0574 0.3010 0.8998 0.073 Uiso 1 1 calc R . .
H12C H 0.0285 0.1008 0.8624 0.073 Uiso 1 1 calc R . .
C13 C 0.05941(9) -0.0217(7) 0.5665(4) 0.0449(9) Uani 1 1 d . . .
H13A H 0.0396 -0.1229 0.6107 0.067 Uiso 1 1 calc R . .
H13B H 0.0800 -0.1020 0.5062 0.067 Uiso 1 1 calc R . .
H13C H 0.0463 0.0800 0.4906 0.067 Uiso 1 1 calc R . .
C14 C 0.19386(10) 0.3347(6) 0.9976(5) 0.0456(8) Uani 1 1 d . . .
H14A H 0.2140 0.3275 1.0859 0.068 Uiso 1 1 calc R . .
H14B H 0.1683 0.3810 1.0449 0.068 Uiso 1 1 calc R . .
H14C H 0.2024 0.4385 0.9127 0.068 Uiso 1 1 calc R . .
C15 C 0.17230(10) 0.5671(5) 0.4937(5) 0.0451(8) Uani 1 1 d . . .
H15A H 0.1957 0.6512 0.4775 0.054 Uiso 1 1 calc R . .
H15B H 0.1470 0.6357 0.5007 0.054 Uiso 1 1 calc R . .
C1S C 0.04010(10) 0.5141(7) 0.2348(5) 0.0548(9) Uani 1 1 d . . .
H1S1 H 0.0332 0.5797 0.3420 0.082 Uiso 1 1 calc R . .
H1S2 H 0.0315 0.3628 0.2338 0.082 Uiso 1 1 calc R . .
H1S3 H 0.0267 0.5928 0.1450 0.082 Uiso 1 1 calc R . .
O1S O 0.08166(6) 0.5244(4) 0.2111(4) 0.0532(7) Uani 1 1 d . . .
H1S H 0.0878 0.6464 0.1733 0.080 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 0.0407(11) 0.0303(11) 0.0285(10) -0.0002(9) -0.0026(8) 0.0004(9)
O2 0.0460(11) 0.0331(13) 0.0253(10) -0.0003(9) 0.0031(8) -0.0087(9)
C1 0.0299(14) 0.0413(17) 0.0325(15) -0.0028(14) -0.0047(11) 0.0070(13)
C2 0.0260(13) 0.064(2) 0.0373(17) -0.0040(17) 0.0023(12) -0.0002(14)
C3 0.0314(14) 0.0471(19) 0.0323(15) -0.0041(15) 0.0060(13) -0.0068(13)
C4 0.0378(15) 0.0339(18) 0.0227(13) -0.0070(12) 0.0018(12) -0.0035(12)
C5 0.0311(14) 0.0270(15) 0.0266(14) -0.0022(13) -0.0004(11) 0.0028(11)
C6 0.0300(13) 0.0293(16) 0.0317(15) 0.0018(13) -0.0020(11) 0.0053(12)
C7 0.0354(14) 0.0284(16) 0.0297(14) -0.0042(12) 0.0036(11) -0.0052(12)
C8 0.0360(14) 0.0216(15) 0.0291(14) 0.0012(12) 0.0035(12) -0.0033(11)
C9 0.0417(16) 0.0309(16) 0.0279(14) -0.0007(14) -0.0022(12) 0.0016(12)
C10 0.0295(14) 0.0406(19) 0.0266(14) -0.0028(12) -0.0048(11) 0.0029(12)
C11 0.0272(13) 0.0398(18) 0.0288(14) 0.0043(13) 0.0003(11) -0.0008(12)
C12 0.0311(15) 0.070(3) 0.0455(19) 0.0046(18) 0.0052(14) 0.0081(16)
C13 0.0323(15) 0.065(3) 0.0376(17) 0.0025(16) -0.0029(12) -0.0171(16)
C14 0.0445(18) 0.046(2) 0.0465(19) -0.0149(17) 0.0088(16) -0.0146(14)
C15 0.0451(17) 0.034(2) 0.056(2) -0.0038(18) 0.0069(16) -0.0075(13)
C1S 0.0490(19) 0.053(2) 0.062(2) 0.0077(19) -0.0057(17) -0.0066(16)
O1S 0.0466(13) 0.0375(14) 0.0756(18) 0.0192(13) -0.0111(12) -0.0038(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 C5 1.439(3) . ?
O1 H1 0.8400 . ?
O2 C8 1.441(3) . ?
O2 H2 0.8400 . ?
C1 C10 1.336(4) . ?
C1 C2 1.496(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.542(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.509(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C15 1.321(5) . ?
C4 C5 1.524(4) . ?
C5 C6 1.530(4) . ?
C5 H5 1.0000 . ?
C6 C11 1.547(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.532(4) . ?
C7 C11 1.540(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.531(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.511(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C14 1.497(5) . ?
C11 C12 1.532(4) . ?
C11 C13 1.537(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9500 . ?
C15 H15B 0.9500 . ?
C1S O1S 1.407(4) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
O1S H1S 0.8400 . ?

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
C5 O1 H1 109.5 . . ?
C8 O2 H2 109.5 . . ?
C10 C1 C2 127.5(3) . . ?
C10 C1 H1A 116.3 . . ?
C2 C1 H1A 116.3 . . ?
C1 C2 C3 113.6(2) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 112.9(2) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C15 C4 C3 121.9(3) . . ?
C15 C4 C5 121.6(3) . . ?
C3 C4 C5 116.3(3) . . ?
O1 C5 C4 108.3(2) . . ?
O1 C5 C6 111.7(2) . . ?
C4 C5 C6 115.3(2) . . ?
O1 C5 H5 107.1 . . ?
C4 C5 H5 107.1 . . ?
C6 C5 H5 107.1 . . ?
C5 C6 C11 116.2(3) . . ?
C5 C6 H6A 108.2 . . ?
C11 C6 H6A 108.2 . . ?
C5 C6 H6B 108.2 . . ?
C11 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
C8 C7 C11 116.9(3) . . ?
C8 C7 H7A 108.1 . . ?
C11 C7 H7A 108.1 . . ?
C8 C7 H7B 108.1 . . ?
C11 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
O2 C8 C9 110.6(2) . . ?
O2 C8 C7 107.9(2) . . ?
C9 C8 C7 113.3(2) . . ?
O2 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C7 C8 H8 108.3 . . ?
C10 C9 C8 111.4(2) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C1 C10 C14 123.7(3) . . ?
C1 C10 C9 121.8(3) . . ?
C14 C10 C9 114.4(3) . . ?
C12 C11 C13 108.5(2) . . ?
C12 C11 C7 110.8(2) . . ?
C13 C11 C7 107.7(3) . . ?
C12 C11 C6 108.0(3) . . ?
C13 C11 C6 111.3(2) . . ?
C7 C11 C6 110.5(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 H15A 120.0 . . ?
C4 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
O1S C1S H1S1 109.5 . . ?
O1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
O1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C1S O1S H1S 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 -114.0(3) . . . . ?
C1 C2 C3 C4 59.0(4) . . . . ?
C2 C3 C4 C15 95.7(4) . . . . ?
C2 C3 C4 C5 -89.6(3) . . . . ?
C15 C4 C5 O1 76.2(4) . . . . ?
C3 C4 C5 O1 -98.6(3) . . . . ?
C15 C4 C5 C6 -49.7(4) . . . . ?
C3 C4 C5 C6 135.5(3) . . . . ?
O1 C5 C6 C11 79.7(3) . . . . ?
C4 C5 C6 C11 -156.2(2) . . . . ?
C11 C7 C8 O2 105.9(3) . . . . ?
C11 C7 C8 C9 -131.3(3) . . . . ?
O2 C8 C9 C10 -159.9(2) . . . . ?
C7 C8 C9 C10 78.8(3) . . . . ?
C2 C1 C10 C14 -2.0(5) . . . . ?
C2 C1 C10 C9 177.0(3) . . . . ?
C8 C9 C10 C1 -102.2(3) . . . . ?
C8 C9 C10 C14 76.8(3) . . . . ?
C8 C7 C11 C12 -51.9(3) . . . . ?
C8 C7 C11 C13 -170.4(2) . . . . ?
C8 C7 C11 C6 67.8(3) . . . . ?
C5 C6 C11 C12 -169.7(2) . . . . ?
C5 C6 C11 C13 -50.7(3) . . . . ?
C5 C6 C11 C7 69.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        64.98
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.049


_database_code_depnum_ccdc_archive 'CCDC 925951'