# Electronic Supplementary Material (ESI) for ChemComm.
# 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/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_4a
_database_code_depnum_ccdc_archive 'CCDC 1055406'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_audit_creation_date             2012-07-26
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (S,S)-PhCOCH(COCH3)CH(Ph)CHCH2
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 O2'
_chemical_formula_sum            'C19 H18 O2'
_chemical_formula_weight         278.33
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   9.8399(6)
_cell_length_b                   7.9143(5)
_cell_length_c                   10.7479(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.006(8)
_cell_angle_gamma                90.00
_cell_volume                     776.03(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    200
_cell_measurement_reflns_used    1715
_cell_measurement_theta_min      4.43
_cell_measurement_theta_max      67.55

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8596
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID 191R'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            7788
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.44
_diffrn_reflns_theta_max         68.19
_reflns_number_total             2389
_reflns_number_gt                2116
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'RAPID AUTO (Rigaku, 2006)'
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2006)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'

_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)+(0.0525P)²+0.0106P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_number_reflns         2389
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
O1 O 0.49630(15) 0.9034(2) 0.98117(14) 0.0494(4) Uani 1 1 d . . .
O2 O 0.04682(14) 0.8118(2) 0.74869(13) 0.0566(4) Uani 1 1 d . . .
C1 C 0.30037(18) 0.7371(2) 0.83391(18) 0.0325(4) Uani 1 1 d . . .
H1 H 0.3532 0.6446 0.8968 0.039 Uiso 1 1 calc R . .
C2 C 0.3881(2) 0.9003(3) 0.87881(18) 0.0368(4) Uani 1 1 d . . .
C3 C 0.3355(2) 1.0548(3) 0.7941(2) 0.0529(6) Uani 1 1 d . . .
H3A H 0.3801 1.0595 0.7265 0.063 Uiso 1 1 calc R . .
H3B H 0.3635 1.1556 0.8510 0.063 Uiso 1 1 calc R . .
H3C H 0.2286 1.0506 0.7493 0.063 Uiso 1 1 calc R . .
C4 C 0.15093(19) 0.7644(3) 0.84596(19) 0.0373(4) Uani 1 1 d . . .
C5 C 0.1386(2) 0.7407(2) 0.97870(19) 0.0366(5) Uani 1 1 d . . .
C6 C 0.0109(2) 0.7962(3) 0.9939(2) 0.0476(5) Uani 1 1 d . . .
H6 H -0.0645 0.8478 0.9204 0.057 Uiso 1 1 calc R . .
C7 C -0.0069(2) 0.7774(4) 1.1135(2) 0.0580(6) Uani 1 1 d . . .
H7 H -0.0941 0.8163 1.1224 0.070 Uiso 1 1 calc R . .
C8 C 0.1015(3) 0.7019(3) 1.2211(2) 0.0587(6) Uani 1 1 d . . .
H8 H 0.0886 0.6886 1.3038 0.070 Uiso 1 1 calc R . .
C9 C 0.2284(2) 0.6459(3) 1.2085(2) 0.0545(6) Uani 1 1 d . . .
H9 H 0.3028 0.5936 1.2824 0.065 Uiso 1 1 calc R . .
C10 C 0.2469(2) 0.6662(3) 1.08792(19) 0.0447(5) Uani 1 1 d . . .
H10 H 0.3350 0.6286 1.0799 0.054 Uiso 1 1 calc R . .
C11 C 0.28111(18) 0.6842(3) 0.68978(17) 0.0328(4) Uani 1 1 d . . .
H11 H 0.2081 0.7617 0.6253 0.039 Uiso 1 1 calc R . .
C12 C 0.2221(2) 0.5080(3) 0.6638(2) 0.0416(5) Uani 1 1 d . . .
H12 H 0.2824 0.4210 0.7176 0.050 Uiso 1 1 calc R . .
C13 C 0.0960(3) 0.4623(4) 0.5746(2) 0.0635(7) Uani 1 1 d . . .
H13A H 0.0319 0.5447 0.5184 0.076 Uiso 1 1 calc R . .
H13B H 0.0683 0.3466 0.5657 0.076 Uiso 1 1 calc R . .
C14 C 0.42469(18) 0.6969(2) 0.66652(17) 0.0329(4) Uani 1 1 d . . .
C15 C 0.4311(2) 0.7852(3) 0.55816(19) 0.0429(5) Uani 1 1 d . . .
H15 H 0.3458 0.8409 0.4990 0.051 Uiso 1 1 calc R . .
C16 C 0.5600(2) 0.7942(3) 0.5340(2) 0.0519(6) Uani 1 1 d . . .
H16 H 0.5624 0.8556 0.4589 0.062 Uiso 1 1 calc R . .
C17 C 0.6846(2) 0.7139(3) 0.6191(2) 0.0523(6) Uani 1 1 d . . .
H17 H 0.7731 0.7204 0.6033 0.063 Uiso 1 1 calc R . .
C18 C 0.6797(2) 0.6242(3) 0.7272(2) 0.0492(5) Uani 1 1 d . . .
H18 H 0.7651 0.5680 0.7855 0.059 Uiso 1 1 calc R . .
C19 C 0.5508(2) 0.6153(3) 0.75141(19) 0.0413(5) Uani 1 1 d . . .
H19 H 0.5487 0.5533 0.8263 0.050 Uiso 1 1 calc R . .

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
O1 0.0446(7) 0.0520(9) 0.0423(8) -0.0078(8) 0.0057(6) -0.0070(7)
O2 0.0367(7) 0.0856(12) 0.0431(8) 0.0083(9) 0.0100(6) 0.0150(8)
C1 0.0320(9) 0.0334(11) 0.0311(9) 0.0017(8) 0.0107(7) 0.0014(7)
C2 0.0393(10) 0.0364(11) 0.0373(10) -0.0060(9) 0.0174(8) -0.0010(9)
C3 0.0570(13) 0.0344(12) 0.0621(14) 0.0004(11) 0.0164(11) -0.0026(10)
C4 0.0351(9) 0.0390(11) 0.0357(10) -0.0021(9) 0.0111(8) 0.0009(9)
C5 0.0377(9) 0.0335(12) 0.0391(11) -0.0024(8) 0.0150(8) -0.0048(8)
C6 0.0444(11) 0.0493(14) 0.0538(12) 0.0000(11) 0.0236(9) 0.0024(10)
C7 0.0587(14) 0.0635(17) 0.0669(15) -0.0020(14) 0.0408(12) -0.0008(13)
C8 0.0784(16) 0.0568(16) 0.0537(15) -0.0039(12) 0.0395(13) -0.0118(13)
C9 0.0619(14) 0.0610(16) 0.0413(12) 0.0041(12) 0.0199(10) -0.0029(13)
C10 0.0427(10) 0.0509(14) 0.0401(11) 0.0030(11) 0.0150(9) -0.0010(10)
C11 0.0324(9) 0.0346(11) 0.0294(9) -0.0004(8) 0.0095(7) -0.0023(8)
C12 0.0492(11) 0.0367(12) 0.0421(11) -0.0056(9) 0.0207(9) -0.0076(9)
C13 0.0668(16) 0.0578(17) 0.0616(15) -0.0105(13) 0.0191(13) -0.0228(13)
C14 0.0361(9) 0.0331(11) 0.0288(9) -0.0037(8) 0.0114(7) -0.0018(8)
C15 0.0457(11) 0.0446(12) 0.0390(11) 0.0044(10) 0.0165(9) -0.0006(10)
C16 0.0588(13) 0.0557(16) 0.0500(13) 0.0035(12) 0.0304(11) -0.0111(12)
C17 0.0448(12) 0.0588(16) 0.0607(14) -0.0109(12) 0.0283(11) -0.0107(11)
C18 0.0403(10) 0.0563(15) 0.0493(12) -0.0044(11) 0.0148(9) 0.0018(11)
C19 0.0423(10) 0.0457(13) 0.0368(10) 0.0041(9) 0.0158(9) 0.0064(9)

_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 C2 1.211(2) . ?
O2 C4 1.217(2) . ?
C1 C2 1.527(3) . ?
C1 C4 1.539(2) . ?
C1 C11 1.546(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.497(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.488(3) . ?
C5 C10 1.387(3) . ?
C5 C6 1.397(3) . ?
C6 C7 1.368(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.496(3) . ?
C11 C14 1.527(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.303(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
C14 C15 1.380(3) . ?
C14 C19 1.393(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
C2 C1 C4 107.43(16) . . ?
C2 C1 C11 112.84(16) . . ?
C4 C1 C11 111.10(14) . . ?
C2 C1 H1 108.5 . . ?
C4 C1 H1 108.5 . . ?
C11 C1 H1 108.5 . . ?
O1 C2 C3 121.45(19) . . ?
O1 C2 C1 120.30(18) . . ?
C3 C2 C1 118.24(16) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 C5 121.17(17) . . ?
O2 C4 C1 119.62(17) . . ?
C5 C4 C1 119.13(15) . . ?
C10 C5 C6 118.30(19) . . ?
C10 C5 C4 123.49(17) . . ?
C6 C5 C4 118.21(17) . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C5 120.8(2) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C12 C11 C14 110.41(16) . . ?
C12 C11 C1 109.42(16) . . ?
C14 C11 C1 111.88(13) . . ?
C12 C11 H11 108.3 . . ?
C14 C11 H11 108.3 . . ?
C1 C11 H11 108.3 . . ?
C13 C12 C11 126.3(2) . . ?
C13 C12 H12 116.9 . . ?
C11 C12 H12 116.9 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C15 C14 C19 118.45(17) . . ?
C15 C14 C11 120.58(16) . . ?
C19 C14 C11 120.94(17) . . ?
C14 C15 C16 121.16(19) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 119.59(19) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.38(19) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        68.19
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031

# start Validation Reply Form
_vrf_PUBL024_GLOBAL              
;
PROBLEM: The number of authors is greater than 5.
RESPONSE: Naoya Kanbayashi, the main author; 
Kazuki Hosoda, student carrying out the major experiment;
Masanori Kato and Koichiro Takii, students carrying out supporting experiments;
Taka-aki Okamura, specialist of crystallography and advisory staff;
Kiyotaka Onitsuka, leader of the laboratory
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
