# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Prof Andrew B Holmes'
_publ_contact_author_address     
;
Department of Chemistry
University of Cambridge
Lensfield Road
Cambridge
Cambs
CB2 1EW
UNITED KINGDOM
;

_publ_contact_author_email       ABH1@CAM.AC.UK

_publ_section_title              
;
Synthesis of a simplified analogue of eleutherobin
via a Claisen rearrangement and ring closing metathesis strategy
;
loop_
_publ_author_name
'Andrew B. Holmes'
'Andrew Ayscough'
'Andrew Bond'
'Gary C. H. Chiang'
'Sylvie Duckie'
'Gilles Pain'

data_ah0106
_database_code_depnum_ccdc_archive 'CCDC 249051'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H14 O2'
_chemical_formula_weight         166.21

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           tetragonal
_symmetry_space_group_name_H-M   'P 4(3) 2(1) 2'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   8.2007(4)
_cell_length_b                   8.2007(4)
_cell_length_c                   26.5896(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1788.19(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5395
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  1.116
_exptl_absorpt_process_details   'Sortav Blessing (1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      180(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  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_reflns_number            4922
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1997
_reflns_number_gt                1648
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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^)+(0.0810P)^2^+0.0000P] 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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.119(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.2(18)
_refine_ls_number_reflns         1997
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1474
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.187
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002

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 0.69121(17) 0.97932(16) 0.01807(4) 0.0334(4) Uani 1 1 d . . .
O2 O 0.8708(2) 0.73599(18) 0.08008(4) 0.0455(5) Uani 1 1 d . . .
H2 H 0.8975 0.7609 0.0506 0.068 Uiso 1 1 calc R . .
C1 C 0.6270(3) 0.8937(2) 0.06134(7) 0.0349(5) Uani 1 1 d . . .
H1A H 0.5778 0.7887 0.0497 0.042 Uiso 1 1 calc R . .
C2 C 0.7612(3) 0.8551(2) 0.09931(7) 0.0361(5) Uani 1 1 d . . .
H2B H 0.7056 0.8032 0.1287 0.043 Uiso 1 1 calc R . .
C3 C 0.8526(3) 1.0030(3) 0.12026(7) 0.0405(5) Uani 1 1 d . . .
H3A H 0.7723 1.0886 0.1289 0.049 Uiso 1 1 calc R . .
H3B H 0.9083 0.9704 0.1517 0.049 Uiso 1 1 calc R . .
C4 C 0.9770(3) 1.0742(3) 0.08486(8) 0.0439(6) Uani 1 1 d . . .
H4A H 1.0793 1.0201 0.0829 0.053 Uiso 1 1 calc R . .
C5 C 0.9580(3) 1.2047(3) 0.05623(8) 0.0450(6) Uani 1 1 d . . .
H5A H 1.0487 1.2351 0.0361 0.054 Uiso 1 1 calc R . .
C6 C 0.8093(3) 1.3100(3) 0.05200(8) 0.0432(6) Uani 1 1 d . . .
H6A H 0.8433 1.4258 0.0514 0.052 Uiso 1 1 calc R . .
H6B H 0.7404 1.2935 0.0822 0.052 Uiso 1 1 calc R . .
C7 C 0.7078(3) 1.2741(3) 0.00506(8) 0.0419(5) Uani 1 1 d . . .
H7A H 0.6394 1.3706 -0.0023 0.050 Uiso 1 1 calc R . .
H7B H 0.7829 1.2589 -0.0237 0.050 Uiso 1 1 calc R . .
C8 C 0.5978(3) 1.1258(2) 0.00853(7) 0.0348(5) Uani 1 1 d . . .
H8A H 0.5379 1.1129 -0.0240 0.042 Uiso 1 1 calc R . .
C9 C 0.4775(3) 1.1288(3) 0.05051(8) 0.0394(5) Uani 1 1 d . . .
H9A H 0.3988 1.2124 0.0554 0.047 Uiso 1 1 calc R . .
C10 C 0.4941(3) 1.0013(3) 0.07985(8) 0.0400(5) Uani 1 1 d . . .
H10A H 0.4301 0.9807 0.1089 0.048 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 0.0423(8) 0.0320(8) 0.0258(6) 0.0009(5) 0.0014(5) 0.0013(6)
O2 0.0682(11) 0.0367(9) 0.0317(7) 0.0063(6) 0.0003(7) 0.0134(8)
C1 0.0452(12) 0.0282(10) 0.0314(8) 0.0004(7) 0.0023(9) -0.0086(9)
C2 0.0500(13) 0.0315(10) 0.0267(8) 0.0032(8) 0.0029(8) -0.0013(9)
C3 0.0507(14) 0.0409(12) 0.0301(8) -0.0013(8) -0.0074(9) 0.0005(11)
C4 0.0376(12) 0.0482(13) 0.0460(11) -0.0039(11) -0.0050(9) -0.0061(10)
C5 0.0429(13) 0.0422(13) 0.0501(11) -0.0011(10) 0.0000(10) -0.0146(10)
C6 0.0506(14) 0.0289(11) 0.0502(11) -0.0002(9) 0.0013(10) -0.0111(10)
C7 0.0492(13) 0.0347(11) 0.0418(10) 0.0100(9) 0.0042(9) -0.0019(10)
C8 0.0394(12) 0.0343(11) 0.0307(9) 0.0004(8) -0.0036(8) 0.0013(9)
C9 0.0363(12) 0.0385(11) 0.0435(10) -0.0055(9) 0.0024(9) 0.0000(9)
C10 0.0364(12) 0.0452(12) 0.0383(9) -0.0010(9) 0.0066(9) -0.0075(11)

_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 C8 1.447(2) . ?
O1 C1 1.447(2) . ?
O2 C2 1.423(2) . ?
O2 H2 0.8400 . ?
C1 C10 1.486(3) . ?
C1 C2 1.527(3) . ?
C1 H1A 1.0000 . ?
C2 C3 1.530(3) . ?
C2 H2B 1.0000 . ?
C3 C4 1.506(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.323(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.498(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.529(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.517(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.490(3) . ?
C8 H8A 1.0000 . ?
C9 C10 1.312(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 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
C8 O1 C1 110.45(14) . . ?
C2 O2 H2 109.5 . . ?
O1 C1 C10 103.99(15) . . ?
O1 C1 C2 111.34(16) . . ?
C10 C1 C2 115.63(16) . . ?
O1 C1 H1A 108.5 . . ?
C10 C1 H1A 108.5 . . ?
C2 C1 H1A 108.5 . . ?
O2 C2 C1 111.10(14) . . ?
O2 C2 C3 111.43(17) . . ?
C1 C2 C3 115.47(16) . . ?
O2 C2 H2B 106.0 . . ?
C1 C2 H2B 106.0 . . ?
C3 C2 H2B 106.0 . . ?
C4 C3 C2 114.31(16) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C3 126.4(2) . . ?
C5 C4 H4A 116.8 . . ?
C3 C4 H4A 116.8 . . ?
C4 C5 C6 127.3(2) . . ?
C4 C5 H5A 116.4 . . ?
C6 C5 H5A 116.4 . . ?
C5 C6 C7 113.18(18) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 115.37(16) . . ?
C8 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
O1 C8 C9 103.50(15) . . ?
O1 C8 C7 111.17(17) . . ?
C9 C8 C7 115.19(17) . . ?
O1 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C10 C9 C8 111.29(19) . . ?
C10 C9 H9A 124.4 . . ?
C8 C9 H9A 124.4 . . ?
C9 C10 C1 110.68(18) . . ?
C9 C10 H10A 124.7 . . ?
C1 C10 H10A 124.7 . . ?

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
C8 O1 C1 C10 -3.3(2) . . . . ?
C8 O1 C1 C2 -128.42(16) . . . . ?
O1 C1 C2 O2 -68.9(2) . . . . ?
C10 C1 C2 O2 172.76(17) . . . . ?
O1 C1 C2 C3 59.3(2) . . . . ?
C10 C1 C2 C3 -59.1(2) . . . . ?
O2 C2 C3 C4 50.8(2) . . . . ?
C1 C2 C3 C4 -77.2(2) . . . . ?
C2 C3 C4 C5 100.2(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C7 -101.0(3) . . . . ?
C5 C6 C7 C8 79.5(2) . . . . ?
C1 O1 C8 C9 2.91(18) . . . . ?
C1 O1 C8 C7 127.14(16) . . . . ?
C6 C7 C8 O1 -59.6(2) . . . . ?
C6 C7 C8 C9 57.7(3) . . . . ?
O1 C8 C9 C10 -1.4(2) . . . . ?
C7 C8 C9 C10 -123.0(2) . . . . ?
C8 C9 C10 C1 -0.6(2) . . . . ?
O1 C1 C10 C9 2.4(2) . . . . ?
C2 C1 C10 C9 124.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.163