# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_D17075
_database_code_depnum_ccdc_archive 'CCDC 1579272'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H24 O2'
_chemical_formula_weight         248.35

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5853(3)
_cell_length_b                   8.4322(3)
_cell_length_c                   11.3892(4)
_cell_angle_alpha                92.3437(15)
_cell_angle_beta                 91.5258(15)
_cell_angle_gamma                93.7139(15)
_cell_volume                     630.30(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9820
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      33.74

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.148
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7040
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42244
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.423
_diffrn_reflns_theta_max         32.030
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4381
_reflns_number_gt                3771
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2015)'
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Dual I\mS fixed chi instrument. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.1999P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4381
_refine_ls_number_parameters     169
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.07100(11) 0.45654(8) 0.66602(5) 0.01566(14) Uani 1 1 d D . . . .
H1 H 0.978(2) 0.5078(16) 0.6438(12) 0.023 Uiso 1 1 d D U . . .
C1 C 1.16843(13) 0.54331(10) 0.76493(7) 0.01262(15) Uani 1 1 d . . . . .
H1A H 1.141159 0.657055 0.760730 0.015 Uiso 1 1 calc R U . . .
H1AB H 1.317430 0.535002 0.761373 0.015 Uiso 1 1 calc R U . . .
C2 C 1.09423(12) 0.48159(9) 0.88247(7) 0.00898(14) Uani 1 1 d . . . . .
C3 C 1.14691(14) 0.30677(10) 0.88736(7) 0.01295(16) Uani 1 1 d . . . . .
H3A H 1.077997 0.244466 0.820474 0.016 Uiso 1 1 calc R U . . .
H3AB H 1.295581 0.300162 0.879859 0.016 Uiso 1 1 calc R U . . .
C4 C 1.08074(14) 0.23536(10) 1.00275(7) 0.01258(15) Uani 1 1 d . . . . .
H4 H 1.115727 0.121775 1.003884 0.015 Uiso 1 1 calc R U . . .
C5 C 0.84996(13) 0.24524(10) 1.01189(7) 0.01270(15) Uani 1 1 d . . . . .
H5A H 0.803303 0.196455 1.084890 0.015 Uiso 1 1 calc R U . . .
H5AB H 0.779264 0.185978 0.944196 0.015 Uiso 1 1 calc R U . . .
C6 C 0.79816(12) 0.42036(10) 1.01293(7) 0.00981(14) Uani 1 1 d . . . . .
H6 H 0.647635 0.425260 1.019976 0.012 Uiso 1 1 calc R U . . .
C7 C 1.19130(13) 0.33120(10) 1.10536(7) 0.01183(15) Uani 1 1 d . . . . .
H7A H 1.340198 0.325053 1.098714 0.014 Uiso 1 1 calc R U . . .
H7AB H 1.150746 0.285606 1.180638 0.014 Uiso 1 1 calc R U . . .
C8 C 1.13773(12) 0.50567(10) 1.10404(7) 0.00938(14) Uani 1 1 d . . . . .
H8 H 1.211949 0.566669 1.170968 0.011 Uiso 1 1 calc R U . . .
O11 O 0.80088(10) 0.63390(8) 0.55500(6) 0.01592(14) Uani 1 1 d D . . . .
H11 H 0.803(2) 0.6113(17) 0.4859(11) 0.024 Uiso 1 1 d D U . . .
C11 C 0.60615(13) 0.68891(10) 0.58277(7) 0.01058(15) Uani 1 1 d . . . . .
H11A H 0.606597 0.720103 0.667530 0.013 Uiso 1 1 calc R U . . .
H11B H 0.501420 0.600145 0.568249 0.013 Uiso 1 1 calc R U . . .
C12 C 0.54697(12) 0.83036(9) 0.51183(6) 0.00792(14) Uani 1 1 d . . . . .
C13 C 0.50757(13) 0.77036(9) 0.38316(7) 0.01034(15) Uani 1 1 d . . . . .
H13A H 0.632747 0.727106 0.352283 0.012 Uiso 1 1 calc R U . . .
H13B H 0.398809 0.683416 0.379590 0.012 Uiso 1 1 calc R U . . .
C14 C 0.44406(13) 0.90460(10) 0.30677(7) 0.01026(15) Uani 1 1 d . . . . .
H14 H 0.420000 0.863282 0.223674 0.012 Uiso 1 1 calc R U . . .
C15 C 0.24695(12) 0.96646(10) 0.35448(7) 0.01088(15) Uani 1 1 d . . . . .
H15A H 0.138830 0.879063 0.352098 0.013 Uiso 1 1 calc R U . . .
H15B H 0.200843 1.051668 0.304868 0.013 Uiso 1 1 calc R U . . .
C16 C 0.28495(12) 1.03165(9) 0.48148(7) 0.00865(14) Uani 1 1 d . . . . .
H16 H 0.155892 1.072324 0.511440 0.010 Uiso 1 1 calc R U . . .
C17 C 0.61576(13) 1.03669(10) 0.31223(7) 0.01073(15) Uani 1 1 d . . . . .
H17A H 0.579564 1.123132 0.260876 0.013 Uiso 1 1 calc R U . . .
H17B H 0.742766 0.993769 0.283716 0.013 Uiso 1 1 calc R U . . .
C18 C 0.64939(12) 1.10279(9) 0.43958(7) 0.00860(14) Uani 1 1 d . . . . .
H18 H 0.760014 1.189985 0.441940 0.010 Uiso 1 1 calc R 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
O1 C1 1.4315(10) . ?
O1 H1 0.815(12) . ?
C1 C2 1.5364(11) . ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
C2 C3 1.5390(11) . ?
C2 C8 1.5494(11) 2_767 ?
C2 C6 1.5503(11) 2_767 ?
C3 C4 1.5300(12) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C7 1.5330(12) . ?
C4 C5 1.5335(12) . ?
C4 H4 1.0000 . ?
C5 C6 1.5366(12) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C8 1.5511(11) 2_767 ?
C6 H6 1.0000 . ?
C7 C8 1.5355(11) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8 1.0000 . ?
O11 C11 1.4305(10) . ?
O11 H11 0.803(12) . ?
C11 C12 1.5328(11) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5405(11) . ?
C12 C18 1.5502(11) 2_676 ?
C12 C16 1.5511(11) 2_676 ?
C13 C14 1.5283(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C17 1.5331(12) . ?
C14 C15 1.5344(11) . ?
C14 H14 1.0000 . ?
C15 C16 1.5346(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C18 1.5512(11) 2_676 ?
C16 H16 1.0000 . ?
C17 C18 1.5376(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18 1.0000 . ?

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 H1 107.0(10) . . ?
O1 C1 C2 112.29(7) . . ?
O1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
O1 C1 H1AB 109.1 . . ?
C2 C1 H1AB 109.1 . . ?
H1A C1 H1AB 107.9 . . ?
C1 C2 C3 107.41(6) . . ?
C1 C2 C8 112.26(6) . 2_767 ?
C3 C2 C8 110.06(7) . 2_767 ?
C1 C2 C6 110.61(7) . 2_767 ?
C3 C2 C6 109.58(6) . 2_767 ?
C8 C2 C6 106.91(6) 2_767 2_767 ?
C4 C3 C2 111.18(6) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3AB 109.4 . . ?
C2 C3 H3AB 109.4 . . ?
H3A C3 H3AB 108.0 . . ?
C3 C4 C7 108.82(7) . . ?
C3 C4 C5 108.50(7) . . ?
C7 C4 C5 110.00(7) . . ?
C3 C4 H4 109.8 . . ?
C7 C4 H4 109.8 . . ?
C5 C4 H4 109.8 . . ?
C4 C5 C6 109.46(7) . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5AB 109.8 . . ?
C6 C5 H5AB 109.8 . . ?
H5A C5 H5AB 108.2 . . ?
C5 C6 C2 111.73(6) . 2_767 ?
C5 C6 C8 109.67(6) . 2_767 ?
C2 C6 C8 109.36(6) 2_767 2_767 ?
C5 C6 H6 108.7 . . ?
C2 C6 H6 108.7 2_767 . ?
C8 C6 H6 108.7 2_767 . ?
C4 C7 C8 110.00(6) . . ?
C4 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C4 C7 H7AB 109.7 . . ?
C8 C7 H7AB 109.7 . . ?
H7A C7 H7AB 108.2 . . ?
C7 C8 C2 110.53(7) . 2_767 ?
C7 C8 C6 110.41(6) . 2_767 ?
C2 C8 C6 108.88(6) 2_767 2_767 ?
C7 C8 H8 109.0 . . ?
C2 C8 H8 109.0 2_767 . ?
C6 C8 H8 109.0 2_767 . ?
C11 O11 H11 109.3(11) . . ?
O11 C11 C12 113.77(7) . . ?
O11 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
O11 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 107.83(6) . . ?
C11 C12 C18 110.01(6) . 2_676 ?
C13 C12 C18 109.44(6) . 2_676 ?
C11 C12 C16 112.19(6) . 2_676 ?
C13 C12 C16 109.98(6) . 2_676 ?
C18 C12 C16 107.37(6) 2_676 2_676 ?
C14 C13 C12 111.00(6) . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C17 108.53(6) . . ?
C13 C14 C15 108.37(7) . . ?
C17 C14 C15 110.86(6) . . ?
C13 C14 H14 109.7 . . ?
C17 C14 H14 109.7 . . ?
C15 C14 H14 109.7 . . ?
C14 C15 C16 109.58(6) . . ?
C14 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C15 C16 C12 111.05(6) . 2_676 ?
C15 C16 C18 109.96(6) . 2_676 ?
C12 C16 C18 109.16(6) 2_676 2_676 ?
C15 C16 H16 108.9 . . ?
C12 C16 H16 108.9 2_676 . ?
C18 C16 H16 108.9 2_676 . ?
C14 C17 C18 109.66(6) . . ?
C14 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
C14 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C17 C18 C12 111.40(6) . 2_676 ?
C17 C18 C16 109.43(6) . 2_676 ?
C12 C18 C16 108.98(6) 2_676 2_676 ?
C17 C18 H18 109.0 . . ?
C12 C18 H18 109.0 2_676 . ?
C16 C18 H18 109.0 2_676 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O11 0.815(12) 1.922(13) 2.7165(9) 164.6(14) .
O11 H11 O1 0.803(12) 2.017(13) 2.7693(9) 155.9(14) 2_766

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.074


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
