# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1501632'
_audit_update_record             
;
2016-08-30 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H24 O3'
_chemical_formula_sum            'C15 H24 O3'
_chemical_formula_weight         252.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   9.97920(10)
_cell_length_b                   6.68480(10)
_cell_length_c                   10.2099(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.735(7)
_cell_angle_gamma                90
_cell_volume                     676.39(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8662
_cell_measurement_theta_min      6.60
_cell_measurement_theta_max      68.10

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.673
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9042
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         6.602
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             2363
_reflns_number_gt                2096
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     0.927
_reflns_Friedel_fraction_full    0.934

_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       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0645P)²+0.0616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 817 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2363
_refine_ls_number_parameters     168
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.156
_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_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 0.2383(3) 0.9622(4) -0.1702(2) 0.0495(7) Uani 1 1 d . . . . .
O2 O 0.5684(3) 0.7121(4) 0.2463(3) 0.0532(7) Uani 1 1 d D . . . .
H2O H 0.617(4) 0.611(5) 0.251(4) 0.064 Uiso 1 1 d D U . . .
O3 O 0.4340(3) 0.4537(4) 0.1915(3) 0.0611(8) Uani 1 1 d . . . . .
C1 C 0.2516(4) 0.7492(7) -0.1927(3) 0.0511(9) Uani 1 1 d . . . . .
H1A H 0.3298 0.7229 -0.2381 0.061 Uiso 1 1 calc R U . . .
H1B H 0.1720 0.6985 -0.2461 0.061 Uiso 1 1 calc R U . . .
C2 C 0.2676(4) 0.6495(5) -0.0584(3) 0.0398(8) Uani 1 1 d . . . . .
H2 H 0.3285 0.5344 -0.0582 0.048 Uiso 1 1 calc R U . . .
C3 C 0.1321(4) 0.5850(6) -0.0155(3) 0.0445(9) Uani 1 1 d . . . . .
H3A H 0.0664 0.6903 -0.0376 0.053 Uiso 1 1 calc R U . . .
H3B H 0.1007 0.4664 -0.0645 0.053 Uiso 1 1 calc R U . . .
C4 C 0.1397(4) 0.5406(5) 0.1311(3) 0.0410(8) Uani 1 1 d . . . . .
H4A H 0.1980 0.4262 0.1523 0.049 Uiso 1 1 calc R U . . .
H4B H 0.0504 0.5073 0.1532 0.049 Uiso 1 1 calc R U . . .
C5 C 0.1945(3) 0.7214(5) 0.2128(3) 0.0346(7) Uani 1 1 d . . . . .
H5 H 0.1348 0.8318 0.1809 0.042 Uiso 1 1 calc R U . . .
C6 C 0.1796(4) 0.7074(5) 0.3632(3) 0.0410(8) Uani 1 1 d . . . . .
C7 C 0.2550(5) 0.5301(6) 0.4309(4) 0.0553(10) Uani 1 1 d . . . . .
H7A H 0.2256 0.4088 0.3860 0.083 Uiso 1 1 calc R U . . .
H7B H 0.2365 0.5229 0.5210 0.083 Uiso 1 1 calc R U . . .
H7C H 0.3502 0.5470 0.4284 0.083 Uiso 1 1 calc R U . . .
C8 C 0.2616(4) 1.0009(5) -0.0311(3) 0.0442(8) Uani 1 1 d . . . . .
H8A H 0.1769 1.0204 0.0049 0.053 Uiso 1 1 calc R U . . .
H8B H 0.3168 1.1195 -0.0136 0.053 Uiso 1 1 calc R U . . .
C9 C 0.3343(3) 0.8175(5) 0.0290(3) 0.0352(7) Uani 1 1 d . . . . .
H9 H 0.4284 0.8268 0.0108 0.042 Uiso 1 1 calc R U . . .
C10 C 0.2301(4) 0.9047(6) 0.4291(4) 0.0462(9) Uani 1 1 d . . . . .
H10A H 0.1667 1.0101 0.3997 0.055 Uiso 1 1 calc R U . . .
H10B H 0.2306 0.8913 0.5237 0.055 Uiso 1 1 calc R U . . .
C11 C 0.3705(4) 0.9680(6) 0.4004(3) 0.0480(9) Uani 1 1 d . . . . .
H11A H 0.3936 1.0957 0.4421 0.058 Uiso 1 1 calc R U . . .
H11B H 0.4364 0.8700 0.4365 0.058 Uiso 1 1 calc R U . . .
C12 C 0.3741(4) 0.9856(5) 0.2524(3) 0.0407(8) Uani 1 1 d . . . . .
H12A H 0.4640 1.0251 0.2354 0.049 Uiso 1 1 calc R U . . .
H12B H 0.3118 1.0893 0.2177 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3363(3) 0.7877(4) 0.1805(3) 0.0320(7) Uani 1 1 d . . . . .
C14 C 0.4466(3) 0.6308(5) 0.2104(3) 0.0369(7) Uani 1 1 d . . . . .
C15 C 0.0302(4) 0.6888(8) 0.3810(4) 0.0598(11) Uani 1 1 d . . . . .
H15A H 0.0191 0.7027 0.4727 0.090 Uiso 1 1 calc R U . . .
H15B H -0.0026 0.5602 0.3501 0.090 Uiso 1 1 calc R U . . .
H15C H -0.0199 0.7919 0.3313 0.090 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 C8 1.436(4) . ?
O1 C1 1.450(5) . ?
O2 C14 1.343(4) . ?
O2 H2O 0.83(3) . ?
O3 C14 1.204(4) . ?
C1 C2 1.516(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.531(5) . ?
C2 C9 1.537(5) . ?
C2 H2 0.9800 . ?
C3 C4 1.519(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.533(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C13 1.554(4) . ?
C5 C6 1.562(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.525(5) . ?
C6 C15 1.528(5) . ?
C6 C10 1.538(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.517(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C13 1.558(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.525(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.520(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.538(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.525(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 O1 C1 109.0(2) . . ?
C14 O2 H2O 101(3) . . ?
O1 C1 C2 106.9(3) . . ?
O1 C1 H1A 110.3 . . ?
C2 C1 H1A 110.3 . . ?
O1 C1 H1B 110.3 . . ?
C2 C1 H1B 110.3 . . ?
H1A C1 H1B 108.6 . . ?
C1 C2 C3 112.3(3) . . ?
C1 C2 C9 101.3(3) . . ?
C3 C2 C9 112.1(3) . . ?
C1 C2 H2 110.3 . . ?
C3 C2 H2 110.3 . . ?
C9 C2 H2 110.3 . . ?
C4 C3 C2 113.1(3) . . ?
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 . . ?
C3 C4 C5 110.8(3) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C13 112.6(2) . . ?
C4 C5 C6 114.7(3) . . ?
C13 C5 C6 114.8(3) . . ?
C4 C5 H5 104.4 . . ?
C13 C5 H5 104.4 . . ?
C6 C5 H5 104.4 . . ?
C7 C6 C15 108.6(3) . . ?
C7 C6 C10 110.5(3) . . ?
C15 C6 C10 107.0(3) . . ?
C7 C6 C5 113.2(3) . . ?
C15 C6 C5 109.2(3) . . ?
C10 C6 C5 108.3(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C9 105.6(3) . . ?
O1 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
O1 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C8 C9 C2 101.6(3) . . ?
C8 C9 C13 117.1(3) . . ?
C2 C9 C13 115.9(2) . . ?
C8 C9 H9 107.2 . . ?
C2 C9 H9 107.2 . . ?
C13 C9 H9 107.2 . . ?
C11 C10 C6 114.5(3) . . ?
C11 C10 H10A 108.6 . . ?
C6 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C6 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 110.0(3) . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 C13 112.0(3) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 111.4(3) . . ?
C14 C13 C5 114.6(2) . . ?
C12 C13 C5 108.8(2) . . ?
C14 C13 C9 102.2(2) . . ?
C12 C13 C9 109.7(2) . . ?
C5 C13 C9 110.0(2) . . ?
O3 C14 O2 121.1(3) . . ?
O3 C14 C13 125.8(3) . . ?
O2 C14 C13 112.7(3) . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
O2 H2O O1 0.83(3) 2.00(3) 2.733(4) 146(4) 2_645

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.081

_shelxl_version_number           2014-3

