# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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data_w
_database_code_depnum_ccdc_archive 'CCDC 901005'
#TrackingRef 'X-ray of 3-(ethylthio)-2-(4-methoxyphenyl)-4-phenylcyclopent-2-enone.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 O2 S'
_chemical_formula_weight         324.42
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'
S S 0.1246 0.1234 '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/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                   19.0155(8)
_cell_length_b                   8.2100(3)
_cell_length_c                   11.6450(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.291(4)
_cell_angle_gamma                90.00
_cell_volume                     1735.83(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(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  'Oxford diffraction Gemini R Ultra'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6642
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3048
_reflns_number_gt                2397
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrysAlis (Oxford Diffraction,2006)'
_computing_cell_refinement       CrysAlis
_computing_data_reduction        CrysAlis
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0501P)^2^+0.3350P] where P=(Fo^2^+2Fc^2^)/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         3037
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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
S1 S 0.19022(3) 0.43768(8) 0.89183(4) 0.0654(2) Uani 1 1 d . . .
C13 C 0.26840(11) 0.5327(2) 0.87779(15) 0.0473(4) Uani 1 1 d . . .
C14 C 0.33990(11) 0.5417(2) 0.97971(16) 0.0515(5) Uani 1 1 d . . .
H14 H 0.3316 0.5998 1.0480 0.062 Uiso 1 1 calc R . .
C15 C 0.27382(10) 0.5996(2) 0.77424(15) 0.0474(4) Uani 1 1 d . . .
C1 C 0.37255(10) 0.3752(2) 1.02028(15) 0.0429(4) Uani 1 1 d . . .
C2 C 0.36993(11) 0.2520(2) 0.93830(16) 0.0504(5) Uani 1 1 d . . .
H2 H 0.3455 0.2690 0.8573 0.060 Uiso 1 1 calc R . .
C7 C 0.21826(10) 0.6043(2) 0.65465(15) 0.0457(4) Uani 1 1 d . . .
C3 C 0.40934(11) 0.3474(2) 1.14002(16) 0.0531(5) Uani 1 1 d . . .
H3 H 0.4118 0.4293 1.1962 0.064 Uiso 1 1 calc R . .
O1 O 0.36766(9) 0.7567(2) 0.72735(14) 0.0877(6) Uani 1 1 d . . .
O2 O 0.07069(9) 0.6061(2) 0.30954(12) 0.0853(5) Uani 1 1 d . . .
C16 C 0.34590(12) 0.6758(2) 0.79747(18) 0.0583(5) Uani 1 1 d . . .
C8 C 0.14657(11) 0.6533(3) 0.63728(17) 0.0598(5) Uani 1 1 d . . .
H8 H 0.1319 0.6848 0.7034 0.072 Uiso 1 1 calc R . .
C4 C 0.40319(12) 0.1041(2) 0.97543(19) 0.0578(5) Uani 1 1 d . . .
H4 H 0.4011 0.0221 0.9194 0.069 Uiso 1 1 calc R . .
C9 C 0.18773(11) 0.5616(3) 0.44077(18) 0.0629(6) Uani 1 1 d . . .
H9 H 0.2021 0.5302 0.3744 0.076 Uiso 1 1 calc R . .
C10 C 0.11657(11) 0.6096(3) 0.42557(17) 0.0590(5) Uani 1 1 d . . .
C5 C 0.43929(11) 0.0773(2) 1.0944(2) 0.0595(5) Uani 1 1 d . . .
H5 H 0.4615 -0.0228 1.1192 0.071 Uiso 1 1 calc R . .
C6 C 0.44259(11) 0.1985(3) 1.17710(18) 0.0604(5) Uani 1 1 d . . .
H6 H 0.4671 0.1807 1.2580 0.072 Uiso 1 1 calc R . .
C11 C 0.09575(11) 0.6568(3) 0.52419(18) 0.0656(6) Uani 1 1 d . . .
H11 H 0.0477 0.6910 0.5148 0.079 Uiso 1 1 calc R . .
C12 C 0.23805(11) 0.5594(3) 0.55346(17) 0.0560(5) Uani 1 1 d . . .
H12 H 0.2862 0.5272 0.5621 0.067 Uiso 1 1 calc R . .
C18 C 0.20787(14) 0.4086(3) 1.05199(19) 0.0762(7) Uani 1 1 d . . .
H18A H 0.2465 0.3284 1.0813 0.091 Uiso 1 1 calc R . .
H18B H 0.2239 0.5102 1.0941 0.091 Uiso 1 1 calc R . .
C17 C 0.39013(13) 0.6434(3) 0.92630(18) 0.0690(7) Uani 1 1 d . . .
H17A H 0.4035 0.7449 0.9700 0.083 Uiso 1 1 calc R . .
H17B H 0.4348 0.5839 0.9297 0.083 Uiso 1 1 calc R . .
C19 C 0.13831(15) 0.3514(4) 1.0751(2) 0.0923(8) Uani 1 1 d . . .
H19A H 0.1012 0.4340 1.0501 0.138 Uiso 1 1 calc R . .
H19B H 0.1477 0.3303 1.1594 0.138 Uiso 1 1 calc R . .
H19C H 0.1216 0.2533 1.0304 0.138 Uiso 1 1 calc R . .
C20 C -0.00084(14) 0.6733(5) 0.2878(2) 0.1218(13) Uani 1 1 d . . .
H20A H -0.0285 0.6089 0.3281 0.183 Uiso 1 1 calc R . .
H20B H -0.0255 0.6734 0.2029 0.183 Uiso 1 1 calc R . .
H20C H 0.0031 0.7829 0.3177 0.183 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
S1 0.0641(4) 0.0852(4) 0.0487(3) 0.0097(3) 0.0194(3) -0.0037(3)
C13 0.0611(12) 0.0386(9) 0.0415(9) -0.0001(8) 0.0143(8) 0.0046(8)
C14 0.0716(13) 0.0397(10) 0.0379(9) -0.0026(8) 0.0079(9) -0.0029(9)
C15 0.0573(11) 0.0411(10) 0.0421(10) 0.0018(8) 0.0122(8) 0.0038(9)
C1 0.0478(10) 0.0432(10) 0.0393(9) 0.0017(8) 0.0153(8) -0.0039(8)
C2 0.0641(12) 0.0489(11) 0.0401(10) 0.0004(8) 0.0183(9) -0.0007(9)
C7 0.0510(11) 0.0449(10) 0.0418(9) 0.0048(8) 0.0147(8) 0.0039(8)
C3 0.0587(12) 0.0564(12) 0.0410(10) -0.0001(9) 0.0097(9) 0.0007(10)
O1 0.0833(11) 0.0976(12) 0.0687(10) 0.0352(9) 0.0017(8) -0.0342(9)
O2 0.0586(9) 0.1420(16) 0.0473(8) 0.0171(9) 0.0035(7) -0.0106(10)
C16 0.0683(13) 0.0468(11) 0.0509(11) 0.0102(9) 0.0039(10) -0.0079(10)
C8 0.0629(13) 0.0753(14) 0.0463(11) 0.0087(10) 0.0241(10) 0.0174(11)
C4 0.0681(13) 0.0474(11) 0.0633(13) -0.0031(10) 0.0277(11) 0.0044(10)
C9 0.0568(12) 0.0915(16) 0.0431(10) -0.0029(11) 0.0190(9) 0.0021(11)
C10 0.0504(12) 0.0790(14) 0.0448(11) 0.0142(10) 0.0100(9) -0.0060(10)
C5 0.0532(12) 0.0540(12) 0.0742(14) 0.0131(11) 0.0233(11) 0.0113(10)
C6 0.0546(12) 0.0721(14) 0.0498(11) 0.0137(11) 0.0084(9) 0.0068(10)
C11 0.0483(12) 0.0907(16) 0.0593(12) 0.0193(12) 0.0183(10) 0.0180(11)
C12 0.0460(11) 0.0740(13) 0.0497(11) 0.0008(10) 0.0167(9) 0.0068(10)
C18 0.0880(17) 0.0926(17) 0.0546(13) 0.0115(12) 0.0314(12) -0.0027(14)
C17 0.0835(15) 0.0500(12) 0.0569(12) 0.0103(10) -0.0046(11) -0.0226(11)
C19 0.103(2) 0.114(2) 0.0763(16) 0.0146(15) 0.0520(15) 0.0047(17)
C20 0.0547(16) 0.220(4) 0.0774(18) 0.046(2) -0.0001(13) 0.008(2)
_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
S1 C13 1.729(2) . ?
S1 C18 1.810(2) . ?
C13 C15 1.357(2) . ?
C13 C14 1.518(3) . ?
C14 C1 1.517(2) . ?
C14 C17 1.533(3) . ?
C15 C16 1.457(3) . ?
C15 C7 1.477(2) . ?
C1 C3 1.381(2) . ?
C1 C2 1.382(2) . ?
C2 C4 1.378(3) . ?
C7 C8 1.377(3) . ?
C7 C12 1.389(3) . ?
C3 C6 1.385(3) . ?
O1 C16 1.217(2) . ?
O2 C10 1.374(2) . ?
O2 C20 1.419(3) . ?
C16 C17 1.510(3) . ?
C8 C11 1.383(3) . ?
C4 C5 1.369(3) . ?
C9 C10 1.369(3) . ?
C9 C12 1.375(3) . ?
C10 C11 1.377(3) . ?
C5 C6 1.373(3) . ?
C18 C19 1.501(3) . ?
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
C13 S1 C18 104.81(10) . . ?
C15 C13 C14 112.85(17) . . ?
C15 C13 S1 124.14(15) . . ?
C14 C13 S1 122.93(13) . . ?
C1 C14 C13 112.84(14) . . ?
C1 C14 C17 111.74(17) . . ?
C13 C14 C17 103.34(14) . . ?
C13 C15 C16 108.94(16) . . ?
C13 C15 C7 128.79(18) . . ?
C16 C15 C7 122.25(16) . . ?
C3 C1 C2 118.68(17) . . ?
C3 C1 C14 120.08(16) . . ?
C2 C1 C14 121.14(15) . . ?
C4 C2 C1 120.63(17) . . ?
C8 C7 C12 117.31(17) . . ?
C8 C7 C15 123.04(17) . . ?
C12 C7 C15 119.65(17) . . ?
C1 C3 C6 120.56(18) . . ?
C10 O2 C20 117.5(2) . . ?
O1 C16 C15 126.77(18) . . ?
O1 C16 C17 124.26(19) . . ?
C15 C16 C17 108.94(17) . . ?
C7 C8 C11 121.80(18) . . ?
C5 C4 C2 120.29(18) . . ?
C10 C9 C12 120.51(19) . . ?
C9 C10 O2 115.81(19) . . ?
C9 C10 C11 119.42(18) . . ?
O2 C10 C11 124.77(19) . . ?
C4 C5 C6 119.87(18) . . ?
C5 C6 C3 119.96(18) . . ?
C10 C11 C8 119.70(19) . . ?
C9 C12 C7 121.26(18) . . ?
C19 C18 S1 108.80(18) . . ?
C16 C17 C14 105.59(16) . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040