# Supplementary Material (ESI) for Perkin Transactions # This journal is (c) The Royal Society of Chemistry 2000 # CCDC Number: 207/394 data_km0299 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C9 H18 O2' _chemical_formula_sum 'C9 H18 O2' _chemical_formula_weight 158.23 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 Pbna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x, -y-1/2, -z' '-x-1/2, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 8.2540(16) _cell_length_b 11.2290(15) _cell_length_c 20.088(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1861.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11 _cell_measurement_theta_max 21.3 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.129 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 ? _diffrn_measurement_method 'non-profiled omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 182 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2044 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0671 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 2 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 23.95 _reflns_number_total 1454 _reflns_number_gt 933 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1992)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1992)' _computing_data_reduction 'XCAD4 (Harms, 1996)' _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 w=1/[\s^2^(Fo^2^)+(0.0760P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1454 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0977 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1405 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5184(2) 0.72388(17) 0.29558(9) 0.0243(5) Uani 1 d . . . H1 H 0.440(4) 0.766(3) 0.2743(16) 0.039(9) Uiso 1 d . . . O2 O 0.2086(2) 0.35557(16) 0.27281(9) 0.0191(5) Uani 1 d . . . H2 H 0.287(4) 0.307(3) 0.2866(16) 0.043(10) Uiso 1 d . . . C1 C 0.2954(3) 0.4686(2) 0.37739(12) 0.0166(6) Uani 1 d . . . H1A H 0.3863 0.4097 0.3788 0.020 Uiso 1 calc R . . C2 C 0.1636(3) 0.4266(2) 0.32865(12) 0.0156(6) Uani 1 d . . . H2A H 0.1026 0.4978 0.3123 0.019 Uiso 1 calc R . . C3 C 0.0668(3) 0.3688(2) 0.38647(12) 0.0169(6) Uani 1 d . . . C4 C 0.1732(3) 0.4435(2) 0.43442(12) 0.0207(7) Uani 1 d . . . H4A H 0.2198 0.3965 0.4715 0.025 Uiso 1 calc R . . H4B H 0.1187 0.5159 0.4513 0.025 Uiso 1 calc R . . C5 C 0.4629(3) 0.6050(2) 0.30772(13) 0.0180(6) Uani 1 d . . . H5A H 0.5579 0.5516 0.3114 0.022 Uiso 1 calc R . . H5B H 0.3976 0.5781 0.2692 0.022 Uiso 1 calc R . . C6 C 0.3617(3) 0.5943(2) 0.37048(12) 0.0162(6) Uani 1 d . . . H6 H 0.2676 0.6499 0.3663 0.019 Uiso 1 calc R . . C7 C 0.4580(4) 0.6299(2) 0.43228(13) 0.0255(7) Uani 1 d . . . H7A H 0.3882 0.6245 0.4716 0.038 Uiso 1 calc R . . H7B H 0.4969 0.7119 0.4273 0.038 Uiso 1 calc R . . H7C H 0.5508 0.5763 0.4376 0.038 Uiso 1 calc R . . C8 C -0.1146(3) 0.3955(2) 0.38784(13) 0.0216(7) Uani 1 d . . . H8A H -0.1316 0.4818 0.3869 0.032 Uiso 1 calc R . . H8B H -0.1621 0.3625 0.4286 0.032 Uiso 1 calc R . . H8C H -0.1666 0.3591 0.3490 0.032 Uiso 1 calc R . . C9 C 0.0981(3) 0.2361(2) 0.39199(13) 0.0240(7) Uani 1 d . . . H9A H 0.0521 0.2062 0.4337 0.036 Uiso 1 calc R . . H9B H 0.2151 0.2213 0.3914 0.036 Uiso 1 calc R . . H9C H 0.0473 0.1950 0.3543 0.036 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 0.0177(10) 0.0236(11) 0.0316(11) 0.0105(9) -0.0041(9) -0.0052(9) O2 0.0173(10) 0.0223(10) 0.0176(10) -0.0034(8) -0.0020(9) 0.0027(9) C1 0.0148(14) 0.0174(13) 0.0175(13) 0.0004(12) -0.0023(12) 0.0013(12) C2 0.0150(14) 0.0159(13) 0.0161(13) -0.0041(11) -0.0007(11) 0.0035(11) C3 0.0161(14) 0.0187(14) 0.0161(13) 0.0001(11) 0.0003(11) -0.0016(12) C4 0.0227(16) 0.0228(15) 0.0167(14) 0.0023(12) -0.0013(12) -0.0036(13) C5 0.0158(14) 0.0166(14) 0.0217(14) 0.0012(11) 0.0004(12) -0.0037(12) C6 0.0135(13) 0.0156(13) 0.0193(13) -0.0004(11) -0.0009(12) -0.0010(12) C7 0.0284(17) 0.0254(16) 0.0226(15) -0.0026(12) 0.0012(13) -0.0109(14) C8 0.0185(15) 0.0221(14) 0.0242(14) -0.0006(12) 0.0023(12) -0.0017(13) C9 0.0203(14) 0.0221(14) 0.0296(16) 0.0041(13) -0.0024(13) -0.0026(13) _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 C5 1.432(3) . ? O2 C2 1.425(3) . ? C1 C6 1.520(3) . ? C1 C2 1.538(4) . ? C1 C4 1.552(4) . ? C2 C3 1.552(4) . ? C3 C9 1.516(4) . ? C3 C8 1.527(4) . ? C3 C4 1.550(4) . ? C5 C6 1.517(4) . ? C6 C7 1.528(4) . ? 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 C6 C1 C2 118.8(2) . . ? C6 C1 C4 118.0(2) . . ? C2 C1 C4 87.40(19) . . ? O2 C2 C1 119.2(2) . . ? O2 C2 C3 119.3(2) . . ? C1 C2 C3 90.91(19) . . ? C9 C3 C8 111.0(2) . . ? C9 C3 C4 112.9(2) . . ? C8 C3 C4 116.0(2) . . ? C9 C3 C2 112.2(2) . . ? C8 C3 C2 115.9(2) . . ? C4 C3 C2 86.98(18) . . ? C3 C4 C1 90.44(19) . . ? O1 C5 C6 113.1(2) . . ? C5 C6 C1 110.4(2) . . ? C5 C6 C7 111.6(2) . . ? C1 C6 C7 110.9(2) . . ? 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 O2 99.0(3) . . . . ? C4 C1 C2 O2 -140.3(2) . . . . ? C6 C1 C2 C3 -136.3(2) . . . . ? C4 C1 C2 C3 -15.57(19) . . . . ? O2 C2 C3 C9 26.7(3) . . . . ? C1 C2 C3 C9 -98.0(2) . . . . ? O2 C2 C3 C8 -102.2(3) . . . . ? C1 C2 C3 C8 133.2(2) . . . . ? O2 C2 C3 C4 140.2(2) . . . . ? C1 C2 C3 C4 15.6(2) . . . . ? C9 C3 C4 C1 97.4(2) . . . . ? C8 C3 C4 C1 -132.9(2) . . . . ? C2 C3 C4 C1 -15.45(19) . . . . ? C6 C1 C4 C3 137.0(2) . . . . ? C2 C1 C4 C3 15.59(19) . . . . ? O1 C5 C6 C1 175.4(2) . . . . ? O1 C5 C6 C7 -60.9(3) . . . . ? C2 C1 C6 C5 -69.9(3) . . . . ? C4 C1 C6 C5 -173.4(2) . . . . ? C2 C1 C6 C7 165.9(2) . . . . ? C4 C1 C6 C7 62.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.91(4) 1.84(4) 2.754(3) 176(3) 7_666 O2 H2 O1 0.89(4) 1.87(4) 2.734(3) 164(3) 2_645 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 23.95 _refine_diff_density_max 0.19 _refine_diff_density_min -0.27 _refine_diff_density_rms 0.057