# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 152854

data_sw0001

_database_code_CSD	152854


_journal_coden_Cambridge      207

_publ_requested_journal       'Perkin Transactions 1'

loop_
_publ_author_name
'Boesen, Thomas'
'Davies, John E.'
'Eastgate, Martin D.'
'Fox, David J.'
'Medlock, Jonathan A.'
'Tyzack, Charles R.'
'Warren, Stuart'

_publ_contact_author_name     	'Dr Stuart Warren'  
_publ_contact_author_address 
;
Dr Stuart Warren
University Chemical Laboratory
University of Cambridge
Lensfield Road
Cambridge
CB2 1EW
UNITED KINGDOM
;

_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C18 H20 O3' 
_chemical_formula_weight          284.34 
_chemical_melting_point           ? 
_chemical_compound_source         ? 

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) 

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

_cell_length_a                    11.3620(10) 
_cell_length_b                    4.8730(5) 
_cell_length_c                    13.9800(8) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  100.937(6) 
_cell_angle_gamma                 90.00 
_cell_volume                      759.97(11) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     180(2) 
_cell_measurement_reflns_used     4145
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       25.03

_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.18 
_exptl_crystal_size_mid           0.08 
_exptl_crystal_size_min           0.08 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.243 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              304 
_exptl_absorpt_coefficient_mu     0.083 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       180(2) 
_diffrn_radiation_wavelength      0.71070 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'Nonius KappaCCD' 
_diffrn_measurement_method        ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             4628 
_diffrn_reflns_av_R_equivalents   0.0441 
_diffrn_reflns_av_sigmaI/netI     0.0602 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -5 
_diffrn_reflns_limit_k_max        5 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          3.18 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              2306 
_reflns_number_observed           1963 
_reflns_observed_criterion        >2sigma(I) 

_computing_data_collection         
; 
"Collect" data collection software, Nonius B.V., 1998. 
; 
_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor 1997)' 
_computing_data_reduction          
; 
"Collect" data collection software, Nonius B.V., 1998. 
; 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 


_refine_special_details 
; 
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
or flagged by the user for potential systematic errors.  Weighted R-factors 
wR and all goodnesses 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 observed criterion 
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.0855P] 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     ? 
_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    0.09(150) 
_refine_ls_number_reflns          2306 
_refine_ls_number_parameters      193 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0551 
_refine_ls_R_factor_obs           0.0425 
_refine_ls_wR_factor_all          0.1003 
_refine_ls_wR_factor_obs          0.0932 
_refine_ls_goodness_of_fit_all    1.058 
_refine_ls_goodness_of_fit_obs    1.073 
_refine_ls_restrained_S_all       1.057 
_refine_ls_restrained_S_obs       1.072 
_refine_ls_shift/esd_max          0.001 
_refine_ls_shift/esd_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_thermal_displace_type 
_atom_site_occupancy 
_atom_site_calc_flag 
_atom_site_refinement_flags 
_atom_site_disorder_group 
O1 O 0.44158(13) 0.2781(3) 0.55588(10) 0.0340(4) Uani 1 d . . 
H100 H 0.4698(19) 0.4107(29) 0.5913(7) 0.058(9) Uiso 1 calc R . 
O2 O 0.53622(13) -0.2332(3) 0.63824(10) 0.0360(4) Uani 1 d . . 
H101 H 0.5432(18) -0.1632(26) 0.5847(8) 0.054 Uiso 1 calc R . 
O3 O 0.7086(2) 0.6631(4) 0.97130(12) 0.0596(6) Uani 1 d . . 
C1 C 0.0463(2) 0.3421(6) 0.2871(2) 0.0545(7) Uani 1 d . . 
H1 H 0.1229(2) 0.4256(6) 0.3049(2) 0.065 Uiso 1 calc R . 
C2 C -0.0323(2) 0.4363(7) 0.2065(2) 0.0645(9) Uani 1 d . . 
H2 H -0.0091(2) 0.5826(7) 0.1692(2) 0.077 Uiso 1 calc R . 
C3 C -0.1440(2) 0.3210(7) 0.1794(2) 0.0548(8) Uani 1 d . . 
H3 H -0.1979(2) 0.3866(7) 0.1238(2) 0.066 Uiso 1 calc R . 
C4 C -0.1766(2) 0.1104(7) 0.2336(2) 0.0560(8) Uani 1 d . . 
H4 H -0.2536(2) 0.0292(7) 0.2154(2) 0.067 Uiso 1 calc R . 
C5 C -0.0979(2) 0.0146(7) 0.3149(2) 0.0484(7) Uani 1 d . . 
H5 H -0.1222(2) -0.1309(7) 0.3521(2) 0.058 Uiso 1 calc R . 
C6 C 0.0155(2) 0.1273(6) 0.3429(2) 0.0391(6) Uani 1 d . . 
C7 C 0.0981(2) 0.0118(6) 0.4269(2) 0.0413(6) Uani 1 d . . 
H7 H 0.0648(2) -0.1186(6) 0.4648(2) 0.050 Uiso 1 calc R . 
C8 C 0.2121(2) 0.0673(5) 0.4559(2) 0.0389(6) Uani 1 d . . 
H8 H 0.2445(2) 0.2128(5) 0.4238(2) 0.047 Uiso 1 calc R . 
C9 C 0.2957(2) -0.0791(5) 0.5353(2) 0.0382(6) Uani 1 d . . 
H9A H 0.3477(2) -0.2014(5) 0.5049(2) 0.046 Uiso 1 calc R . 
H9B H 0.2475(2) -0.1966(5) 0.5710(2) 0.046 Uiso 1 calc R . 
C10 C 0.3751(2) 0.1039(5) 0.60842(14) 0.0324(5) Uani 1 d . . 
H10 H 0.3233(2) 0.2202(5) 0.64242(14) 0.039 Uiso 1 calc R . 
C11 C 0.4612(2) -0.0625(5) 0.68466(15) 0.0322(5) Uani 1 d . . 
H11 H 0.4117(2) -0.1852(5) 0.71860(15) 0.039 Uiso 1 calc R . 
C12 C 0.5342(2) 0.1210(5) 0.76056(14) 0.0330(5) Uani 1 d . . 
C13 C 0.4861(2) 0.2009(5) 0.84166(15) 0.0414(6) Uani 1 d . . 
H13 H 0.4108(2) 0.1297(5) 0.84971(15) 0.050 Uiso 1 calc R . 
C14 C 0.5463(2) 0.3805(6) 0.9096(2) 0.0476(7) Uani 1 d . . 
H14 H 0.5125(2) 0.4318(6) 0.9641(2) 0.057 Uiso 1 calc R . 
C15 C 0.6554(2) 0.4860(5) 0.8990(2) 0.0433(7) Uani 1 d . . 
C16 C 0.7056(2) 0.4110(5) 0.8194(2) 0.0408(6) Uani 1 d . . 
H16 H 0.7808(2) 0.4834(5) 0.8117(2) 0.049 Uiso 1 calc R . 
C17 C 0.6436(2) 0.2279(5) 0.7513(2) 0.0368(6) Uani 1 d . . 
H17 H 0.6778(2) 0.1755(5) 0.6971(2) 0.044 Uiso 1 calc R . 
C18 C 0.8192(3) 0.7828(7) 0.9608(2) 0.0697(9) Uani 1 d . . 
H18A H 0.8479(3) 0.9038(7) 1.0163(2) 0.105 Uiso 1 calc R . 
H18B H 0.8079(3) 0.8895(7) 0.9003(2) 0.105 Uiso 1 calc R . 
H18C H 0.8784(3) 0.6377(7) 0.9584(2) 0.105 Uiso 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 0.0421(9) 0.0248(9) 0.0324(8) -0.0003(7) 0.0005(6) -0.0026(8) 
O2 0.0438(9) 0.0277(9) 0.0339(8) -0.0004(7) 0.0008(7) 0.0066(8) 
O3 0.0765(13) 0.0528(14) 0.0424(10) -0.0111(10) -0.0065(9) -0.0050(11) 
C1 0.0440(15) 0.054(2) 0.059(2) 0.0098(15) -0.0065(11) -0.0060(13) 
C2 0.060(2) 0.069(2) 0.059(2) 0.016(2) -0.0040(13) 0.003(2) 
C3 0.049(2) 0.068(2) 0.0424(14) -0.0009(15) -0.0045(11) 0.021(2) 
C4 0.0332(14) 0.079(2) 0.051(2) -0.008(2) -0.0025(11) 0.0043(15) 
C5 0.0310(13) 0.066(2) 0.0473(14) 0.0011(14) 0.0049(10) -0.0026(13) 
C6 0.0307(12) 0.050(2) 0.0361(12) -0.0061(12) 0.0036(9) 0.0039(12) 
C7 0.0334(13) 0.050(2) 0.0395(13) 0.0056(12) 0.0036(10) 0.0009(12) 
C8 0.0367(13) 0.038(2) 0.0404(13) -0.0011(12) 0.0019(10) -0.0021(11) 
C9 0.0344(13) 0.0368(15) 0.0401(12) 0.0011(12) -0.0009(9) -0.0016(11) 
C10 0.0320(12) 0.0318(14) 0.0331(11) 0.0007(11) 0.0051(9) 0.0023(10) 
C11 0.0369(13) 0.0260(13) 0.0335(12) 0.0025(10) 0.0061(9) 0.0003(10) 
C12 0.0373(12) 0.0311(13) 0.0282(11) 0.0043(10) 0.0005(9) 0.0059(11) 
C13 0.0461(15) 0.045(2) 0.0335(12) 0.0011(11) 0.0083(10) 0.0017(12) 
C14 0.062(2) 0.049(2) 0.0326(12) -0.0030(13) 0.0092(11) 0.0050(14) 
C15 0.059(2) 0.035(2) 0.0298(12) -0.0015(11) -0.0082(11) 0.0049(13) 
C16 0.0395(13) 0.038(2) 0.0401(13) 0.0031(12) -0.0050(10) 0.0003(12) 
C17 0.0401(14) 0.036(2) 0.0329(12) -0.0004(11) 0.0038(9) 0.0042(11) 
C18 0.092(2) 0.051(2) 0.053(2) -0.004(2) -0.0182(14) -0.013(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 
O1 C10 1.428(3) . ? 
O1 H100 0.84 . ? 
O2 C11 1.432(3) . ? 
O2 H101 0.84 . ? 
O3 C15 1.378(3) . ? 
O3 C18 1.419(3) . ? 
C1 C2 1.377(3) . ? 
C1 C6 1.389(4) . ? 
C1 H1 0.95 . ? 
C2 C3 1.373(4) . ? 
C2 H2 0.95 . ? 
C3 C4 1.368(4) . ? 
C3 H3 0.95 . ? 
C4 C5 1.386(3) . ? 
C4 H4 0.95 . ? 
C5 C6 1.387(3) . ? 
C5 H5 0.95 . ? 
C6 C7 1.470(3) . ? 
C7 C8 1.310(3) . ? 
C7 H7 0.95 . ? 
C8 C9 1.498(3) . ? 
C8 H8 0.95 . ? 
C9 C10 1.518(3) . ? 
C9 H9A 0.99 . ? 
C9 H9B 0.99 . ? 
C10 C11 1.534(3) . ? 
C10 H10 1.00 . ? 
C11 C12 1.510(3) . ? 
C11 H11 1.00 . ? 
C12 C17 1.376(3) . ? 
C12 C13 1.404(3) . ? 
C13 C14 1.375(3) . ? 
C13 H13 0.95 . ? 
C14 C15 1.375(3) . ? 
C14 H14 0.95 . ? 
C15 C16 1.392(3) . ? 
C16 C17 1.394(3) . ? 
C16 H16 0.95 . ? 
C17 H17 0.95 . ? 
C18 H18A 0.98 . ? 
C18 H18B 0.98 . ? 
C18 H18C 0.98 . ? 

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 
C10 O1 H100 109.47(11) . . ? 
C11 O2 H101 109.47(11) . . ? 
C15 O3 C18 117.1(2) . . ? 
C2 C1 C6 121.1(3) . . ? 
C2 C1 H1 119.4(2) . . ? 
C6 C1 H1 119.43(14) . . ? 
C3 C2 C1 120.7(3) . . ? 
C3 C2 H2 119.6(2) . . ? 
C1 C2 H2 119.6(2) . . ? 
C4 C3 C2 119.2(2) . . ? 
C4 C3 H3 120.4(2) . . ? 
C2 C3 H3 120.4(2) . . ? 
C3 C4 C5 120.4(3) . . ? 
C3 C4 H4 119.8(2) . . ? 
C5 C4 H4 119.8(2) . . ? 
C4 C5 C6 121.2(3) . . ? 
C4 C5 H5 119.4(2) . . ? 
C6 C5 H5 119.42(15) . . ? 
C5 C6 C1 117.4(2) . . ? 
C5 C6 C7 119.5(2) . . ? 
C1 C6 C7 123.2(2) . . ? 
C8 C7 C6 127.7(2) . . ? 
C8 C7 H7 116.14(15) . . ? 
C6 C7 H7 116.14(14) . . ? 
C7 C8 C9 125.6(2) . . ? 
C7 C8 H8 117.2(2) . . ? 
C9 C8 H8 117.22(13) . . ? 
C8 C9 C10 115.6(2) . . ? 
C8 C9 H9A 108.39(13) . . ? 
C10 C9 H9A 108.39(13) . . ? 
C8 C9 H9B 108.39(13) . . ? 
C10 C9 H9B 108.39(13) . . ? 
H9A C9 H9B 107.4 . . ? 
O1 C10 C9 107.9(2) . . ? 
O1 C10 C11 110.0(2) . . ? 
C9 C10 C11 112.1(2) . . ? 
O1 C10 H10 108.92(12) . . ? 
C9 C10 H10 108.92(12) . . ? 
C11 C10 H10 108.92(11) . . ? 
O2 C11 C12 111.5(2) . . ? 
O2 C11 C10 110.4(2) . . ? 
C12 C11 C10 111.6(2) . . ? 
O2 C11 H11 107.72(11) . . ? 
C12 C11 H11 107.72(12) . . ? 
C10 C11 H11 107.72(11) . . ? 
C17 C12 C13 117.9(2) . . ? 
C17 C12 C11 123.0(2) . . ? 
C13 C12 C11 119.0(2) . . ? 
C14 C13 C12 121.1(2) . . ? 
C14 C13 H13 119.47(14) . . ? 
C12 C13 H13 119.47(14) . . ? 
C13 C14 C15 120.2(2) . . ? 
C13 C14 H14 119.88(14) . . ? 
C15 C14 H14 119.88(13) . . ? 
C14 C15 O3 115.7(2) . . ? 
C14 C15 C16 120.2(2) . . ? 
O3 C15 C16 124.1(2) . . ? 
C15 C16 C17 118.9(2) . . ? 
C15 C16 H16 120.56(15) . . ? 
C17 C16 H16 120.56(14) . . ? 
C12 C17 C16 121.8(2) . . ? 
C12 C17 H17 119.12(12) . . ? 
C16 C17 H17 119.12(14) . . ? 
O3 C18 H18A 109.47(14) . . ? 
O3 C18 H18B 109.47(13) . . ? 
H18A C18 H18B 109.5 . . ? 
O3 C18 H18C 109.5(2) . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 

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 0.5(5) . . . . ? 
C1 C2 C3 C4 0.0(5) . . . . ? 
C2 C3 C4 C5 0.0(4) . . . . ? 
C3 C4 C5 C6 -0.5(4) . . . . ? 
C4 C5 C6 C1 0.9(4) . . . . ? 
C4 C5 C6 C7 -177.3(2) . . . . ? 
C2 C1 C6 C5 -0.9(4) . . . . ? 
C2 C1 C6 C7 177.3(3) . . . . ? 
C5 C6 C7 C8 170.5(3) . . . . ? 
C1 C6 C7 C8 -7.6(4) . . . . ? 
C6 C7 C8 C9 -172.6(2) . . . . ? 
C7 C8 C9 C10 -133.5(3) . . . . ? 
C8 C9 C10 O1 -56.5(3) . . . . ? 
C8 C9 C10 C11 -177.8(2) . . . . ? 
O1 C10 C11 O2 -61.1(2) . . . . ? 
C9 C10 C11 O2 58.9(2) . . . . ? 
O1 C10 C11 C12 63.5(2) . . . . ? 
C9 C10 C11 C12 -176.5(2) . . . . ? 
O2 C11 C12 C17 33.8(3) . . . . ? 
C10 C11 C12 C17 -90.2(3) . . . . ? 
O2 C11 C12 C13 -150.2(2) . . . . ? 
C10 C11 C12 C13 85.9(3) . . . . ? 
C17 C12 C13 C14 0.1(4) . . . . ? 
C11 C12 C13 C14 -176.2(2) . . . . ? 
C12 C13 C14 C15 0.2(4) . . . . ? 
C13 C14 C15 O3 -179.7(2) . . . . ? 
C13 C14 C15 C16 -0.2(4) . . . . ? 
C18 O3 C15 C14 -177.9(2) . . . . ? 
C18 O3 C15 C16 2.6(4) . . . . ? 
C14 C15 C16 C17 -0.1(4) . . . . ? 
O3 C15 C16 C17 179.4(2) . . . . ? 
C13 C12 C17 C16 -0.3(3) . . . . ? 
C11 C12 C17 C16 175.8(2) . . . . ? 
C15 C16 C17 C12 0.3(4) . . . . ? 

_refine_diff_density_max    0.140 
_refine_diff_density_min   -0.164 
_refine_diff_density_rms    0.035