# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_jiayx-2
_database_code_depnum_ccdc_archive 'CCDC 972952'
_audit_update_record             
;
2013-11-20 deposited with the CCDC.
2014-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 O2'
_chemical_formula_sum            'C15 H22 O2'
_chemical_formula_weight         234.33
_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   P2(1)2(1)2(1)
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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                   6.9058(15)
_cell_length_b                   12.139(2)
_cell_length_c                   15.599(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1307.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    48
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      17.98

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2037
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0849
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1874
_reflns_number_gt                1005
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_cell_refinement       'XSCANS (Bruker, 1997)'
_computing_data_reduction        'XSCANS (Bruker, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'

_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)+(0.0010P)²+0.5000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1874
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1283
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
O1 O 0.5185(4) 0.66455(15) 0.42128(12) 0.0478(6) Uani 1 1 d . . .
O2 O 0.4823(5) 0.80623(19) 0.50547(17) 0.0794(8) Uani 1 1 d . . .
C1 C 0.4677(6) 0.7075(3) 0.4979(2) 0.0548(10) Uani 1 1 d U . .
C2 C 0.4069(6) 0.6346(3) 0.5693(2) 0.0664(12) Uani 1 1 d U . .
H2A H 0.3004 0.6692 0.5996 0.080 Uiso 1 1 calc R . .
H2B H 0.5138 0.6273 0.6093 0.080 Uiso 1 1 calc R . .
C3 C 0.3448(6) 0.5214(3) 0.5410(2) 0.0580(12) Uani 1 1 d . . .
H3A H 0.2160 0.5256 0.5165 0.070 Uiso 1 1 calc R . .
H3B H 0.3386 0.4733 0.5906 0.070 Uiso 1 1 calc R . .
C4 C 0.4831(6) 0.4717(2) 0.47489(19) 0.0475(9) Uani 1 1 d . . .
C5 C 0.4921(5) 0.5480(2) 0.39585(17) 0.0371(8) Uani 1 1 d . . .
C6 C 0.3015(5) 0.5478(2) 0.34322(18) 0.0391(9) Uani 1 1 d . . .
H6 H 0.1995 0.5794 0.3793 0.047 Uiso 1 1 calc R . .
C7 C 0.2398(6) 0.4290(3) 0.3194(2) 0.0576(11) Uani 1 1 d . . .
H7A H 0.1163 0.4311 0.2899 0.069 Uiso 1 1 calc R . .
H7B H 0.3347 0.3974 0.2807 0.069 Uiso 1 1 calc R . .
C8 C 0.2222(6) 0.3568(3) 0.3984(2) 0.0636(12) Uani 1 1 d . . .
H8A H 0.1891 0.2823 0.3814 0.076 Uiso 1 1 calc R . .
H8B H 0.1195 0.3844 0.4349 0.076 Uiso 1 1 calc R . .
C9 C 0.4126(5) 0.3560(3) 0.4477(2) 0.0601(12) Uani 1 1 d . . .
H9A H 0.5114 0.3220 0.4123 0.072 Uiso 1 1 calc R . .
H9B H 0.3972 0.3110 0.4986 0.072 Uiso 1 1 calc R . .
C10 C 0.6662(5) 0.5265(3) 0.3387(2) 0.0530(11) Uani 1 1 d . . .
H10A H 0.6630 0.4504 0.3198 0.064 Uiso 1 1 calc R . .
H10B H 0.7834 0.5368 0.3720 0.064 Uiso 1 1 calc R . .
C11 C 0.6740(5) 0.6019(3) 0.2594(2) 0.0615(12) Uani 1 1 d . . .
H11A H 0.6925 0.6776 0.2776 0.074 Uiso 1 1 calc R . .
H11B H 0.7833 0.5813 0.2238 0.074 Uiso 1 1 calc R . .
C12 C 0.4875(5) 0.5931(3) 0.20735(19) 0.0606(11) Uani 1 1 d . . .
H12A H 0.4911 0.6449 0.1600 0.073 Uiso 1 1 calc R . .
H12B H 0.4757 0.5194 0.1838 0.073 Uiso 1 1 calc R . .
C13 C 0.3167(6) 0.6174(3) 0.2635(2) 0.0462(10) Uani 1 1 d . . .
C14 C 0.6858(5) 0.4573(3) 0.5161(2) 0.0658(12) Uani 1 1 d . . .
H14A H 0.6729 0.4203 0.5702 0.099 Uiso 1 1 calc R . .
H14B H 0.7437 0.5283 0.5248 0.099 Uiso 1 1 calc R . .
H14C H 0.7664 0.4142 0.4788 0.099 Uiso 1 1 calc R . .
C15 C 0.1905(6) 0.6952(3) 0.2460(2) 0.0629(12) Uani 1 1 d . . .
H15A H 0.2051 0.7380 0.1970 0.075 Uiso 1 1 calc R . .
H15B H 0.0865 0.7076 0.2827 0.075 Uiso 1 1 calc R . .


_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 1.350(4) . ?
O1 C5 1.481(3) . ?
O2 C1 1.209(4) . ?
C1 C2 1.483(5) . ?
C2 C3 1.506(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.530(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.543(4) . ?
C4 C9 1.546(4) . ?
C4 C14 1.550(5) . ?
C5 C10 1.520(4) . ?
C5 C6 1.551(5) . ?
C6 C13 1.507(4) . ?
C6 C7 1.549(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.516(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.524(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.539(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.527(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.499(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.314(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?

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 C5 125.0(2) . . ?
O2 C1 O1 116.6(3) . . ?
O2 C1 C2 122.8(3) . . ?
O1 C1 C2 120.5(3) . . ?
C1 C2 C3 113.9(3) . . ?
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 . . ?
C2 C3 C4 112.3(3) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 C5 109.1(3) . . ?
C3 C4 C9 110.3(3) . . ?
C5 C4 C9 109.8(3) . . ?
C3 C4 C14 109.2(3) . . ?
C5 C4 C14 111.3(3) . . ?
C9 C4 C14 107.2(3) . . ?
O1 C5 C10 102.9(3) . . ?
O1 C5 C4 111.4(2) . . ?
C10 C5 C4 113.4(3) . . ?
O1 C5 C6 104.4(2) . . ?
C10 C5 C6 111.1(2) . . ?
C4 C5 C6 112.8(3) . . ?
C13 C6 C7 110.1(3) . . ?
C13 C6 C5 112.1(3) . . ?
C7 C6 C5 111.2(3) . . ?
C13 C6 H6 107.7 . . ?
C7 C6 H6 107.7 . . ?
C5 C6 H6 107.7 . . ?
C8 C7 C6 111.5(3) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 110.1(3) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C4 113.9(3) . . ?
C8 C9 H9A 108.8 . . ?
C4 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C4 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C5 C10 C11 113.4(3) . . ?
C5 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C5 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 110.8(3) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 109.8(3) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C15 C13 C12 122.9(3) . . ?
C15 C13 C6 121.9(3) . . ?
C12 C13 C6 115.2(3) . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 120.0 . . ?
C13 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.044
























