# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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
#  on your local computer system.
# 
#  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.
#
data_3aE0
#TrackingRef '12943_web_deposit_cif_file_0_HiroakiYamamoto_1343698827.3aE0.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            3aE0
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 O3'
_chemical_formula_sum            'C13 H18 O3'
_chemical_formula_weight         222.27

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           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.0639(16)
_cell_length_b                   12.459(3)
_cell_length_c                   14.360(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.692(2)
_cell_angle_gamma                90.00
_cell_volume                     1245.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2756
_cell_measurement_theta_min      2.178
_cell_measurement_theta_max      27.438

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'program SADABS ver. 2.03(Sheldrick)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            6900
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         27.44
_reflns_number_total             2815
_reflns_number_gt                2241
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEXII (Bruker AXS, 2006)'
_computing_cell_refinement       'APEXII (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XSHELL ver. 6.31'
_computing_publication_material  'Bruker XSHELL ver. 6.31'

_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)+(0.1000P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2815
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1584
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_restrained_S_all      1.227
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.03673(18) 0.32167(10) 0.24702(8) 0.0377(3) Uani 1 1 d . . .
H3 H -0.0009 0.2742 0.2905 0.045 Uiso 1 1 calc R . .
C1 C 0.17440(16) 0.49179(10) 0.21178(8) 0.0328(3) Uani 1 1 d . . .
C6 C 0.14633(18) 0.46325(10) 0.11774(8) 0.0366(3) Uani 1 1 d . . .
H6 H 0.1817 0.5108 0.0738 0.044 Uiso 1 1 calc R . .
C4 C 0.01289(17) 0.29442(10) 0.15200(9) 0.0364(3) Uani 1 1 d . . .
C5 C 0.06684(18) 0.36560(10) 0.08761(9) 0.0391(3) Uani 1 1 d . . .
H5 H 0.0496 0.3477 0.0239 0.047 Uiso 1 1 calc R . .
C2 C 0.11728(17) 0.42037(10) 0.27693(8) 0.0360(3) Uani 1 1 d . . .
C8 C 0.45508(18) 0.61024(11) 0.25451(10) 0.0416(3) Uani 1 1 d . . .
C11 C 0.5106(2) 0.61951(13) 0.15752(11) 0.0515(4) Uani 1 1 d . . .
C10 C 0.4806(2) 0.71693(14) 0.30611(14) 0.0673(5) Uani 1 1 d . . .
H10A H 0.3961 0.7692 0.2721 0.101 Uiso 1 1 calc R . .
H10B H 0.6112 0.7405 0.3104 0.101 Uiso 1 1 calc R . .
H10C H 0.4506 0.7085 0.3685 0.101 Uiso 1 1 calc R . .
C7 C 0.0963(3) 0.38482(15) 0.43783(10) 0.0654(5) Uani 1 1 d . . .
H7A H -0.0395 0.3713 0.4251 0.098 Uiso 1 1 calc R . .
H7B H 0.1299 0.4173 0.4990 0.098 Uiso 1 1 calc R . .
H7C H 0.1644 0.3183 0.4366 0.098 Uiso 1 1 calc R . .
C9 C 0.5582(2) 0.52181(16) 0.31502(13) 0.0671(5) Uani 1 1 d . . .
H9A H 0.5111 0.5184 0.3739 0.101 Uiso 1 1 calc R . .
H9B H 0.6936 0.5365 0.3270 0.101 Uiso 1 1 calc R . .
H9C H 0.5355 0.4545 0.2826 0.101 Uiso 1 1 calc R . .
C13 C 0.4133(3) 0.70553(18) 0.09476(15) 0.0836(6) Uani 1 1 d . . .
H13A H 0.4725 0.7734 0.1129 0.125 Uiso 1 1 calc R . .
H13B H 0.2799 0.7084 0.1006 0.125 Uiso 1 1 calc R . .
H13C H 0.4246 0.6902 0.0304 0.125 Uiso 1 1 calc R . .
C12 C 0.6398(3) 0.55614(19) 0.12901(16) 0.0866(7) Uani 1 1 d . . .
H12A H 0.6710 0.5649 0.0691 0.104 Uiso 1 1 calc R . .
H12B H 0.6993 0.5028 0.1689 0.104 Uiso 1 1 calc R . .
O1 O 0.24415(12) 0.59230(7) 0.24269(6) 0.0374(3) Uani 1 1 d . . .
O3 O -0.05875(16) 0.19759(8) 0.11900(7) 0.0508(3) Uani 1 1 d . . .
H3O H -0.0979 0.1649 0.1615 0.076 Uiso 1 1 calc R . .
O2 O 0.14614(16) 0.45471(8) 0.36832(6) 0.0533(3) Uani 1 1 d . . .

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
C3 0.0439(7) 0.0316(6) 0.0396(7) 0.0032(5) 0.0130(5) -0.0041(5)
C1 0.0328(6) 0.0254(6) 0.0404(7) -0.0009(5) 0.0068(5) -0.0008(4)
C6 0.0414(6) 0.0324(7) 0.0368(6) 0.0059(5) 0.0092(5) -0.0025(5)
C4 0.0358(6) 0.0295(6) 0.0450(7) -0.0041(5) 0.0102(5) -0.0023(5)
C5 0.0441(7) 0.0387(7) 0.0346(6) -0.0028(5) 0.0068(5) -0.0024(5)
C2 0.0398(6) 0.0331(7) 0.0361(7) -0.0017(5) 0.0096(5) -0.0026(5)
C8 0.0346(6) 0.0381(7) 0.0527(8) -0.0051(6) 0.0088(5) -0.0055(5)
C11 0.0429(8) 0.0560(9) 0.0587(9) -0.0039(7) 0.0175(6) -0.0115(7)
C10 0.0570(10) 0.0589(10) 0.0899(13) -0.0312(9) 0.0241(9) -0.0246(8)
C7 0.0934(13) 0.0649(11) 0.0400(8) 0.0038(8) 0.0172(8) -0.0164(9)
C9 0.0494(9) 0.0729(12) 0.0732(11) 0.0116(10) -0.0062(8) 0.0002(8)
C13 0.0954(15) 0.0784(14) 0.0786(13) 0.0261(11) 0.0194(11) -0.0168(11)
C12 0.0673(11) 0.1117(18) 0.0886(14) -0.0211(12) 0.0354(10) 0.0032(11)
O1 0.0360(5) 0.0275(5) 0.0504(5) -0.0045(4) 0.0125(4) -0.0042(3)
O3 0.0663(7) 0.0366(6) 0.0533(6) -0.0114(4) 0.0214(5) -0.0170(4)
O2 0.0798(7) 0.0470(6) 0.0357(5) -0.0050(4) 0.0170(5) -0.0192(5)

_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
C3 C4 1.3886(18) . ?
C3 C2 1.3922(18) . ?
C3 H3 0.9300 . ?
C1 C6 1.3781(17) . ?
C1 O1 1.3908(15) . ?
C1 C2 1.3990(17) . ?
C6 C5 1.3787(17) . ?
C6 H6 0.9300 . ?
C4 O3 1.3621(15) . ?
C4 C5 1.3803(17) . ?
C5 H5 0.9300 . ?
C2 O2 1.3626(15) . ?
C8 O1 1.4879(15) . ?
C8 C9 1.512(2) . ?
C8 C11 1.514(2) . ?
C8 C10 1.518(2) . ?
C11 C12 1.322(2) . ?
C11 C13 1.492(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C7 O2 1.4133(18) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12A 0.9300 . ?
C12 H12B 0.9300 . ?
O3 H3O 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
C4 C3 C2 119.66(11) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C6 C1 O1 122.00(10) . . ?
C6 C1 C2 118.76(11) . . ?
O1 C1 C2 119.06(10) . . ?
C1 C6 C5 121.27(11) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O3 C4 C5 117.67(11) . . ?
O3 C4 C3 122.34(11) . . ?
C5 C4 C3 119.97(11) . . ?
C6 C5 C4 120.04(11) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
O2 C2 C3 124.17(11) . . ?
O2 C2 C1 115.54(11) . . ?
C3 C2 C1 120.29(11) . . ?
O1 C8 C9 109.42(11) . . ?
O1 C8 C11 108.44(10) . . ?
C9 C8 C11 114.20(13) . . ?
O1 C8 C10 102.80(10) . . ?
C9 C8 C10 110.58(14) . . ?
C11 C8 C10 110.77(12) . . ?
C12 C11 C13 120.92(18) . . ?
C12 C11 C8 122.58(17) . . ?
C13 C11 C8 116.50(14) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C1 O1 C8 117.76(9) . . ?
C4 O3 H3O 109.5 . . ?
C2 O2 C7 118.17(12) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037


_database_code_depnum_ccdc_archive 'CCDC 894295'
