# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TKRKG
_database_code_depnum_ccdc_archive 'CCDC 1488063'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H28 O3'
_chemical_formula_sum            'C17 H28 O3'
_chemical_formula_weight         280.39
_chemical_absolute_configuration unk

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   P212121

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                   4.672(4)
_cell_length_b                   5.359(4)
_cell_length_c                   67.02(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1678(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    360
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   SADABS

_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_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4177
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.1171
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -67
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         1.22
_diffrn_reflns_theta_max         24.79
_reflns_number_total             1649
_reflns_number_gt                832
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0229P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(2)
_refine_ls_number_reflns         1649
_refine_ls_number_parameters     183
_refine_ls_number_restraints     283
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.854
_refine_ls_shift/su_max          0.001
_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
C2 C 0.4812(9) 1.5849(8) 0.03728(6) 0.0510(12) Uani 1 1 d U . .
H2 H 0.6596 1.6798 0.0360 0.061 Uiso 1 1 calc R . .
C5 C 0.3781(8) 1.5806(8) 0.07226(6) 0.0443(12) Uani 1 1 d U . .
H5 H 0.5361 1.6781 0.0779 0.053 Uiso 1 1 calc R . .
C8 C 0.2633(9) 1.1257(7) 0.11695(5) 0.0578(14) Uani 1 1 d U . .
H8A H 0.1559 1.2391 0.1254 0.069 Uiso 1 1 calc R . .
H8B H 0.1266 1.0200 0.1101 0.069 Uiso 1 1 calc R . .
C6 C 0.2309(8) 1.4430(7) 0.08898(5) 0.0496(13) Uani 1 1 d U . .
H6A H 0.0805 1.3403 0.0833 0.059 Uiso 1 1 calc R . .
H6B H 0.1405 1.5644 0.0977 0.059 Uiso 1 1 calc R . .
C1 C 0.4956(9) 1.4174(7) 0.05550(6) 0.0531(13) Uani 1 1 d U . .
H1A H 0.6911 1.3671 0.0582 0.064 Uiso 1 1 calc R . .
H1B H 0.3789 1.2694 0.0537 0.064 Uiso 1 1 calc R . .
C7 C 0.4249(8) 1.2769(7) 0.10161(5) 0.0530(13) Uani 1 1 d U . .
H7A H 0.5283 1.1641 0.0929 0.064 Uiso 1 1 calc R . .
H7B H 0.5645 1.3806 0.1084 0.064 Uiso 1 1 calc R . .
C9 C 0.4490(8) 0.9638(7) 0.13003(5) 0.0604(14) Uani 1 1 d U . .
H9A H 0.5798 1.0695 0.1374 0.072 Uiso 1 1 calc R . .
H9B H 0.5625 0.8546 0.1216 0.072 Uiso 1 1 calc R . .
C11 C 0.4590(9) 0.6447(7) 0.15841(6) 0.0655(15) Uani 1 1 d U . .
H11A H 0.5822 0.7525 0.1662 0.079 Uiso 1 1 calc R . .
H11B H 0.5810 0.5389 0.1503 0.079 Uiso 1 1 calc R . .
C3 C 0.4201(8) 1.4512(7) 0.01824(6) 0.0601(14) Uani 1 1 d U . .
H3A H 0.5700 1.3294 0.0159 0.072 Uiso 1 1 calc R . .
H3B H 0.2410 1.3612 0.0196 0.072 Uiso 1 1 calc R . .
C12 C 0.2887(9) 0.4809(7) 0.17250(6) 0.0663(15) Uani 1 1 d U . .
H12A H 0.1616 0.5861 0.1803 0.080 Uiso 1 1 calc R . .
H12B H 0.1706 0.3690 0.1647 0.080 Uiso 1 1 calc R . .
C10 C 0.2791(9) 0.8055(7) 0.14469(6) 0.0670(15) Uani 1 1 d U . .
H10A H 0.1619 0.9152 0.1528 0.080 Uiso 1 1 calc R . .
H10B H 0.1512 0.6980 0.1372 0.080 Uiso 1 1 calc R . .
C14 C 0.2902(9) 0.1552(7) 0.19973(6) 0.0691(15) Uani 1 1 d U . .
H14A H 0.1481 0.2538 0.2067 0.083 Uiso 1 1 calc R . .
H14B H 0.1892 0.0377 0.1913 0.083 Uiso 1 1 calc R . .
C13 C 0.4681(9) 0.3275(7) 0.18666(6) 0.0740(15) Uani 1 1 d U . .
H13A H 0.5778 0.4388 0.1951 0.089 Uiso 1 1 calc R . .
H13B H 0.6025 0.2281 0.1790 0.089 Uiso 1 1 calc R . .
C15 C 0.4650(10) 0.0114(7) 0.21481(6) 0.0926(18) Uani 1 1 d U . .
H15A H 0.6171 -0.0761 0.2079 0.111 Uiso 1 1 calc R . .
H15B H 0.5534 0.1287 0.2239 0.111 Uiso 1 1 calc R . .
C16 C 0.2997(13) -0.1684(10) 0.22629(8) 0.080(2) Uani 1 1 d U . .
C17 C 0.1584(13) -0.3118(10) 0.23472(8) 0.107(2) Uani 1 1 d U . .
H17 H 0.0451 -0.4268 0.2415 0.129 Uiso 1 1 calc R . .
O3 O -0.0014(6) 1.8855(5) 0.06804(4) 0.0632(11) Uani 1 1 d U . .
O2 O 0.2432(6) 1.7550(5) 0.04154(4) 0.0545(9) Uani 1 1 d U . .
O1 O 0.4012(6) 1.6099(6) 0.00138(4) 0.0827(12) Uani 1 1 d U . .
H1 H 0.2493 1.6864 0.0017 0.124 Uiso 1 1 calc R . .
C4 C 0.1839(10) 1.7538(9) 0.06116(8) 0.0491(15) Uani 1 1 d U . .


_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
C2 O2 1.466(4) . ?
C2 C3 1.491(4) . ?
C2 C1 1.517(4) . ?
C2 H2 0.9800 . ?
C5 C4 1.496(6) . ?
C5 C6 1.508(4) . ?
C5 C1 1.526(4) . ?
C5 H5 0.9800 . ?
C8 C9 1.508(4) . ?
C8 C7 1.511(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 C7 1.527(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.522(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C10 1.514(4) . ?
C11 C12 1.515(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C3 O1 1.417(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C12 C13 1.510(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C14 C15 1.511(4) . ?
C14 C13 1.520(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 C16 1.455(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.160(6) . ?
C17 H17 0.9300 . ?
O3 C4 1.209(5) . ?
O2 C4 1.344(5) . ?
O1 H1 0.8200 . ?

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
O2 C2 C3 108.7(3) . . ?
O2 C2 C1 104.1(3) . . ?
C3 C2 C1 114.4(4) . . ?
O2 C2 H2 109.8 . . ?
C3 C2 H2 109.8 . . ?
C1 C2 H2 109.8 . . ?
C4 C5 C6 113.4(4) . . ?
C4 C5 C1 102.0(4) . . ?
C6 C5 C1 115.5(3) . . ?
C4 C5 H5 108.5 . . ?
C6 C5 H5 108.5 . . ?
C1 C5 H5 108.5 . . ?
C9 C8 C7 114.6(3) . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C5 C6 C7 115.3(3) . . ?
C5 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C2 C1 C5 103.7(3) . . ?
C2 C1 H1A 111.0 . . ?
C5 C1 H1A 111.0 . . ?
C2 C1 H1B 111.0 . . ?
C5 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C8 C7 C6 113.1(3) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
C8 C9 C10 113.3(3) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 C11 C12 114.6(3) . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
O1 C3 C2 113.9(4) . . ?
O1 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
O1 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C13 C12 C11 114.6(4) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C11 C10 C9 114.8(3) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C15 C14 C13 113.6(4) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C12 C13 C14 112.9(4) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C16 C15 C14 113.9(4) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 176.8(7) . . ?
C16 C17 H17 180.0 . . ?
C4 O2 C2 110.1(4) . . ?
C3 O1 H1 109.5 . . ?
O3 C4 O2 121.2(5) . . ?
O3 C4 C5 127.4(5) . . ?
O2 C4 C5 111.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.98
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.99
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.027
