# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008


data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Paul Evans'
'Bernard Allan'
'George Cloughley'
'Patricia Duffy'
'Mazhar Iqbal'
'Agusti Lledo'
'Antoni Riera'
'Xavier Verdaguer'

_publ_contact_author_name        'Paul Evans'
_publ_contact_author_email       PAUL.EVANS@UCD.IE

_publ_section_title              
;
The Conjugate Addition/Peterson Olefination Reaction
for the Preparation
of Cross-Conjugated Cyclopentenone, PPAR-gamma Ligands
;

# Attachment 'mig3am.cif'

data_mig3am
_database_code_depnum_ccdc_archive 'CCDC 219462'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 O'
_chemical_formula_weight         250.32

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   'P b c n'

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

_cell_length_a                   8.8975(5)
_cell_length_b                   12.1847(7)
_cell_length_c                   24.8677(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2696.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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 SMART APEX'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15692
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3200
_reflns_number_gt                2764
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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^)+(0.0760P)^2^+0.7750P] 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         3200
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.2640(2) 0.55798(14) 0.19984(6) 0.0568(5) Uani 1 1 d . . .
H1 H 0.2288 0.4845 0.2018 0.068 Uiso 1 1 calc R . .
C2 C 0.3258(2) 0.59539(15) 0.15210(6) 0.0585(5) Uani 1 1 d . . .
H2 H 0.3315 0.5482 0.1218 0.070 Uiso 1 1 calc R . .
C3 C 0.37844(15) 0.70052(12) 0.14884(5) 0.0380(3) Uani 1 1 d . . .
H3 H 0.4206 0.7269 0.1162 0.046 Uiso 1 1 calc R . .
C4 C 0.37004(16) 0.76801(11) 0.19317(5) 0.0398(3) Uani 1 1 d . . .
H4 H 0.4089 0.8405 0.1912 0.048 Uiso 1 1 calc R . .
C5 C 0.30572(16) 0.73158(10) 0.24053(5) 0.0368(3) Uani 1 1 d . . .
H5 H 0.2982 0.7799 0.2704 0.044 Uiso 1 1 calc R . .
C6 C 0.25202(14) 0.62485(10) 0.24486(5) 0.0320(3) Uani 1 1 d . . .
C7 C 0.18667(14) 0.57720(10) 0.29361(5) 0.0327(3) Uani 1 1 d . . .
H7 H 0.1583 0.5024 0.2899 0.039 Uiso 1 1 calc R . .
C8 C 0.15931(13) 0.61903(9) 0.34244(5) 0.0278(3) Uani 1 1 d . . .
C9 C 0.17828(13) 0.73325(9) 0.36535(5) 0.0271(2) Uani 1 1 d . . .
H9 H 0.2807 0.7618 0.3564 0.033 Uiso 1 1 calc R . .
C10 C 0.05852(17) 0.81181(11) 0.34345(5) 0.0406(3) Uani 1 1 d . . .
H10A H 0.0634 0.8130 0.3041 0.061 Uiso 1 1 calc R . .
H10B H 0.0768 0.8858 0.3574 0.061 Uiso 1 1 calc R . .
H10C H -0.0412 0.7869 0.3548 0.061 Uiso 1 1 calc R . .
C11 C 0.16231(13) 0.72068(9) 0.42731(5) 0.0268(2) Uani 1 1 d . . .
H11 H 0.0918 0.7771 0.4420 0.032 Uiso 1 1 calc R . .
C12 C 0.31399(13) 0.72145(9) 0.45915(5) 0.0289(3) Uani 1 1 d . . .
H12 H 0.3874 0.7799 0.4489 0.035 Uiso 1 1 calc R . .
C13 C 0.26925(15) 0.71779(11) 0.51794(5) 0.0353(3) Uani 1 1 d . . .
H13 H 0.2782 0.7763 0.5430 0.042 Uiso 1 1 calc R . .
C14 C 0.21533(15) 0.61824(11) 0.52828(5) 0.0370(3) Uani 1 1 d . . .
H14 H 0.1781 0.5929 0.5619 0.044 Uiso 1 1 calc R . .
C15 C 0.22431(14) 0.55269(10) 0.47654(5) 0.0322(3) Uani 1 1 d . . .
H15 H 0.2230 0.4710 0.4804 0.039 Uiso 1 1 calc R . .
C16 C 0.36727(14) 0.60256(10) 0.45148(5) 0.0315(3) Uani 1 1 d . . .
H16A H 0.4594 0.5854 0.4722 0.038 Uiso 1 1 calc R . .
H16B H 0.3806 0.5824 0.4132 0.038 Uiso 1 1 calc R . .
C17 C 0.10214(13) 0.60316(9) 0.43858(5) 0.0283(3) Uani 1 1 d . . .
H17 H 0.0007 0.6045 0.4559 0.034 Uiso 1 1 calc R . .
C18 C 0.09939(13) 0.54494(9) 0.38488(5) 0.0288(3) Uani 1 1 d . . .
O1 O 0.05866(11) 0.45045(7) 0.37849(4) 0.0375(2) 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
C1 0.0826(12) 0.0450(8) 0.0429(8) -0.0125(6) 0.0204(8) -0.0276(8)
C2 0.0760(12) 0.0635(10) 0.0360(8) -0.0155(7) 0.0175(7) -0.0237(9)
C3 0.0325(6) 0.0519(8) 0.0295(6) 0.0073(5) 0.0054(5) 0.0020(6)
C4 0.0457(7) 0.0325(6) 0.0413(7) 0.0073(5) 0.0121(6) 0.0022(5)
C5 0.0471(7) 0.0292(6) 0.0340(7) 0.0006(5) 0.0093(5) -0.0013(5)
C6 0.0348(6) 0.0316(6) 0.0295(6) 0.0000(5) 0.0022(5) -0.0050(5)
C7 0.0383(6) 0.0272(6) 0.0326(6) 0.0000(5) 0.0031(5) -0.0082(5)
C8 0.0285(6) 0.0242(5) 0.0307(6) 0.0026(4) 0.0008(4) -0.0038(4)
C9 0.0287(6) 0.0238(5) 0.0288(6) 0.0020(4) 0.0027(4) -0.0019(4)
C10 0.0468(8) 0.0342(6) 0.0409(7) 0.0049(5) -0.0026(6) 0.0095(6)
C11 0.0275(5) 0.0236(5) 0.0293(6) 0.0000(4) 0.0050(4) -0.0013(4)
C12 0.0288(6) 0.0291(6) 0.0287(6) -0.0002(4) 0.0039(4) -0.0052(4)
C13 0.0379(7) 0.0412(7) 0.0268(6) -0.0037(5) 0.0027(5) -0.0064(5)
C14 0.0412(7) 0.0428(7) 0.0270(6) 0.0047(5) 0.0028(5) -0.0060(5)
C15 0.0373(6) 0.0287(6) 0.0306(6) 0.0058(4) 0.0025(5) -0.0026(5)
C16 0.0294(6) 0.0323(6) 0.0327(6) 0.0027(5) 0.0009(5) 0.0004(5)
C17 0.0270(5) 0.0278(5) 0.0300(6) 0.0023(4) 0.0058(4) -0.0042(4)
C18 0.0275(5) 0.0275(5) 0.0314(6) 0.0020(4) 0.0013(4) -0.0039(4)
O1 0.0466(5) 0.0287(4) 0.0373(5) 0.0021(3) 0.0026(4) -0.0133(4)

_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
C1 C2 1.385(2) . ?
C1 C6 1.3887(18) . ?
C2 C3 1.366(2) . ?
C3 C4 1.378(2) . ?
C4 C5 1.3825(17) . ?
C5 C6 1.3896(17) . ?
C6 C7 1.4647(16) . ?
C7 C8 1.3391(16) . ?
C8 C18 1.4876(15) . ?
C8 C9 1.5133(15) . ?
C9 C10 1.5325(17) . ?
C9 C11 1.5549(16) . ?
C11 C17 1.5542(15) . ?
C11 C12 1.5647(17) . ?
C12 C13 1.5157(16) . ?
C12 C16 1.5362(16) . ?
C13 C14 1.3296(18) . ?
C14 C15 1.5166(18) . ?
C15 C16 1.5412(16) . ?
C15 C17 1.5655(17) . ?
C17 C18 1.5124(16) . ?
C18 O1 1.2174(14) . ?

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 C6 121.88(14) . . ?
C3 C2 C1 119.70(14) . . ?
C2 C3 C4 119.57(12) . . ?
C3 C4 C5 120.83(12) . . ?
C4 C5 C6 120.59(12) . . ?
C1 C6 C5 117.40(12) . . ?
C1 C6 C7 117.72(11) . . ?
C5 C6 C7 124.87(11) . . ?
C8 C7 C6 132.20(11) . . ?
C7 C8 C18 118.51(10) . . ?
C7 C8 C9 132.16(10) . . ?
C18 C8 C9 109.33(9) . . ?
C8 C9 C10 111.29(10) . . ?
C8 C9 C11 105.80(9) . . ?
C10 C9 C11 110.50(10) . . ?
C17 C11 C9 107.51(9) . . ?
C17 C11 C12 102.20(9) . . ?
C9 C11 C12 114.97(9) . . ?
C13 C12 C16 99.96(10) . . ?
C13 C12 C11 105.15(9) . . ?
C16 C12 C11 101.40(9) . . ?
C14 C13 C12 107.95(11) . . ?
C13 C14 C15 107.29(11) . . ?
C14 C15 C16 100.30(10) . . ?
C14 C15 C17 105.55(10) . . ?
C16 C15 C17 100.05(9) . . ?
C12 C16 C15 93.84(9) . . ?
C18 C17 C11 106.17(9) . . ?
C18 C17 C15 111.06(10) . . ?
C11 C17 C15 103.38(9) . . ?
O1 C18 C8 126.02(11) . . ?
O1 C18 C17 124.30(10) . . ?
C8 C18 C17 109.63(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -1.6(2) . . . . ?
C3 C4 C5 C6 1.9(2) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 C6 C7 -179.28(17) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 C7 177.88(13) . . . . ?
C1 C6 C7 C8 -179.54(16) . . . . ?
C5 C6 C7 C8 1.8(2) . . . . ?
C6 C7 C8 C18 -176.15(13) . . . . ?
C6 C7 C8 C9 3.5(2) . . . . ?
C7 C8 C9 C10 73.02(17) . . . . ?
C18 C8 C9 C10 -107.33(11) . . . . ?
C7 C8 C9 C11 -166.93(13) . . . . ?
C18 C8 C9 C11 12.73(12) . . . . ?
C8 C9 C11 C17 -11.31(12) . . . . ?
C10 C9 C11 C17 109.26(11) . . . . ?
C8 C9 C11 C12 101.73(11) . . . . ?
C10 C9 C11 C12 -137.70(10) . . . . ?
C17 C11 C12 C13 -68.44(11) . . . . ?
C9 C11 C12 C13 175.44(10) . . . . ?
C17 C11 C12 C16 35.30(10) . . . . ?
C9 C11 C12 C16 -80.82(11) . . . . ?
C16 C12 C13 C14 -33.83(13) . . . . ?
C11 C12 C13 C14 70.98(13) . . . . ?
C12 C13 C14 C15 0.52(14) . . . . ?
C13 C14 C15 C16 32.88(13) . . . . ?
C13 C14 C15 C17 -70.69(13) . . . . ?
C13 C12 C16 C15 50.14(10) . . . . ?
C11 C12 C16 C15 -57.69(10) . . . . ?
C14 C15 C16 C12 -50.06(11) . . . . ?
C17 C15 C16 C12 57.94(10) . . . . ?
C9 C11 C17 C18 5.86(12) . . . . ?
C12 C11 C17 C18 -115.54(10) . . . . ?
C9 C11 C17 C15 122.84(10) . . . . ?
C12 C11 C17 C15 1.44(11) . . . . ?
C14 C15 C17 C18 179.82(9) . . . . ?
C16 C15 C17 C18 76.06(11) . . . . ?
C14 C15 C17 C11 66.34(11) . . . . ?
C16 C15 C17 C11 -37.42(11) . . . . ?
C7 C8 C18 O1 -7.36(19) . . . . ?
C9 C8 C18 O1 172.93(12) . . . . ?
C7 C8 C18 C17 170.32(11) . . . . ?
C9 C8 C18 C17 -9.40(13) . . . . ?
C11 C17 C18 O1 179.72(12) . . . . ?
C15 C17 C18 O1 68.00(15) . . . . ?
C11 C17 C18 C8 1.99(13) . . . . ?
C15 C17 C18 C8 -109.72(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042