Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # 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. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_dc58m _database_code_depnum_ccdc_archive 'CCDC 602444' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H22 O' _chemical_formula_weight 206.32 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 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 9.1809(18) _cell_length_b 6.4336(12) _cell_length_c 11.416(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.320(4) _cell_angle_gamma 90.00 _cell_volume 640.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 1375 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Columnar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.070 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.64221 _exptl_absorpt_correction_T_max 0.92993 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4800 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3005 _reflns_number_gt 1737 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0517P)^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 contr _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 0.00 _refine_ls_number_reflns 3005 _refine_ls_number_parameters 137 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 0.841 _refine_ls_restrained_S_all 0.841 _refine_ls_shift/su_max 0.001 _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 O1 O 1.02793(13) 1.0109(2) 1.04135(9) 0.0770(4) Uani 1 1 d . . . C1 C 0.81306(18) 1.0461(3) 0.85893(13) 0.0608(4) Uani 1 1 d . . . H1A H 0.7957 1.1863 0.8237 0.073 Uiso 1 1 calc R . . C2 C 0.7103(2) 1.0215(4) 0.93942(14) 0.0825(5) Uani 1 1 d . . . H2A H 0.7285 0.8865 0.9792 0.099 Uiso 1 1 calc R . . H2B H 0.7365 1.1269 1.0034 0.099 Uiso 1 1 calc R . . C3 C 0.5421(2) 1.0408(5) 0.86581(18) 0.0973(7) Uani 1 1 d . . . H3A H 0.5211 1.1825 0.8363 0.117 Uiso 1 1 calc R . . H3B H 0.4809 1.0122 0.9194 0.117 Uiso 1 1 calc R . . C4 C 0.4943(2) 0.8929(4) 0.75595(16) 0.0859(6) Uani 1 1 d . . . H4A H 0.3903 0.9318 0.7054 0.103 Uiso 1 1 calc R . . C5 C 0.59894(18) 0.9205(3) 0.67713(13) 0.0687(5) Uani 1 1 d . . . H5A H 0.5841 1.0586 0.6413 0.082 Uiso 1 1 calc R . . H5B H 0.5702 0.8208 0.6100 0.082 Uiso 1 1 calc R . . C6 C 0.76799(17) 0.8915(2) 0.74942(12) 0.0533(4) Uani 1 1 d . . . H6A H 0.7808 0.7505 0.7837 0.064 Uiso 1 1 calc R . . C7 C 0.87261(17) 0.9129(2) 0.66924(12) 0.0563(4) Uani 1 1 d . . . H7A H 0.8614 1.0548 0.6365 0.068 Uiso 1 1 calc R . . C8 C 1.03962(18) 0.8842(3) 0.74801(13) 0.0675(5) Uani 1 1 d . . . H8A H 1.0540 0.7439 0.7806 0.081 Uiso 1 1 calc R . . H8B H 1.1052 0.9022 0.6967 0.081 Uiso 1 1 calc R . . C9 C 1.0870(2) 1.0380(4) 0.85437(14) 0.0766(5) Uani 1 1 d . . . H9A H 1.1905 1.0066 0.9062 0.092 Uiso 1 1 calc R . . H9B H 1.0869 1.1774 0.8219 0.092 Uiso 1 1 calc R . . C10 C 0.98116(19) 1.0299(3) 0.93021(13) 0.0633(4) Uani 1 1 d . . . C11 C 0.4889(3) 0.6662(4) 0.7952(2) 0.1067(8) Uani 1 1 d . . . H11A H 0.4589 0.5790 0.7234 0.160 Uiso 1 1 calc R . . H11B H 0.4159 0.6524 0.8392 0.160 Uiso 1 1 calc R . . H11C H 0.5886 0.6250 0.8477 0.160 Uiso 1 1 calc R . . C12 C 0.83078(19) 0.7656(3) 0.56077(14) 0.0634(4) Uani 1 1 d . . . C13 C 0.8184(3) 0.5387(3) 0.58570(16) 0.0864(6) Uani 1 1 d . . . H13A H 0.8066 0.4611 0.5115 0.130 Uiso 1 1 calc R . . H13B H 0.7309 0.5157 0.6131 0.130 Uiso 1 1 calc R . . H13C H 0.9097 0.4940 0.6485 0.130 Uiso 1 1 calc R . . C14 C 0.8088(2) 0.8341(4) 0.44776(15) 0.0920(7) Uani 1 1 d . . . H14C H 0.7853 0.7412 0.3820 0.110 Uiso 1 1 calc R . . H14A H 0.8169 0.9754 0.4337 0.110 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 0.0843(9) 0.0744(8) 0.0601(7) -0.0073(6) 0.0050(6) -0.0036(7) C1 0.0621(10) 0.0612(10) 0.0573(8) -0.0054(8) 0.0160(7) 0.0026(9) C2 0.0761(12) 0.1052(13) 0.0686(9) -0.0176(12) 0.0259(9) 0.0020(13) C3 0.0742(14) 0.1319(18) 0.0936(13) -0.0125(15) 0.0374(11) 0.0171(14) C4 0.0489(10) 0.1272(18) 0.0772(11) 0.0072(13) 0.0138(9) 0.0111(12) C5 0.0560(10) 0.0834(12) 0.0596(9) 0.0055(9) 0.0079(8) 0.0082(9) C6 0.0521(9) 0.0573(8) 0.0471(7) 0.0026(7) 0.0108(7) 0.0016(7) C7 0.0588(10) 0.0575(9) 0.0522(8) 0.0064(8) 0.0170(7) -0.0011(8) C8 0.0542(10) 0.0843(12) 0.0660(9) -0.0018(10) 0.0216(8) -0.0060(9) C9 0.0562(10) 0.0919(13) 0.0756(10) -0.0040(11) 0.0119(9) -0.0146(11) C10 0.0683(11) 0.0546(9) 0.0593(9) -0.0061(9) 0.0090(8) -0.0042(10) C11 0.0825(15) 0.137(2) 0.1029(15) 0.0067(17) 0.0324(12) -0.0319(15) C12 0.0649(10) 0.0700(10) 0.0551(9) -0.0003(8) 0.0187(7) 0.0007(9) C13 0.1101(16) 0.0690(12) 0.0799(11) -0.0096(11) 0.0293(10) -0.0006(12) C14 0.1162(18) 0.0958(16) 0.0604(10) -0.0006(10) 0.0228(11) -0.0049(12) _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 1.2112(15) . ? C1 C10 1.505(2) . ? C1 C2 1.518(2) . ? C1 C6 1.549(2) . ? C1 H1A 0.9800 . ? C2 C3 1.513(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.524(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.519(2) . ? C4 C11 1.532(3) . ? C4 H4A 0.9800 . ? C5 C6 1.523(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.5271(19) . ? C6 H6A 0.9800 . ? C7 C12 1.510(2) . ? C7 C8 1.525(2) . ? C7 H7A 0.9800 . ? C8 C9 1.520(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.492(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C14 1.318(2) . ? C12 C13 1.499(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14C 0.9300 . ? C14 H14A 0.9300 . ? 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 C1 C2 113.09(13) . . ? C10 C1 C6 111.11(12) . . ? C2 C1 C6 111.24(14) . . ? C10 C1 H1A 107.0 . . ? C2 C1 H1A 107.0 . . ? C6 C1 H1A 107.0 . . ? C3 C2 C1 112.02(14) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 112.69(16) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 110.00(18) . . ? C5 C4 C11 111.65(18) . . ? C3 C4 C11 112.39(18) . . ? C5 C4 H4A 107.5 . . ? C3 C4 H4A 107.5 . . ? C11 C4 H4A 107.5 . . ? C4 C5 C6 113.04(12) . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C5 C6 C7 112.95(11) . . ? C5 C6 C1 109.08(12) . . ? C7 C6 C1 111.54(12) . . ? C5 C6 H6A 107.7 . . ? C7 C6 H6A 107.7 . . ? C1 C6 H6A 107.7 . . ? C12 C7 C8 110.93(14) . . ? C12 C7 C6 112.91(12) . . ? C8 C7 C6 109.92(11) . . ? C12 C7 H7A 107.6 . . ? C8 C7 H7A 107.6 . . ? C6 C7 H7A 107.6 . . ? C9 C8 C7 112.00(15) . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 111.46(14) . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? O1 C10 C9 122.03(15) . . ? O1 C10 C1 122.62(14) . . ? C9 C10 C1 115.35(12) . . ? C4 C11 H11A 109.5 . . ? C4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C14 C12 C13 120.97(17) . . ? C14 C12 C7 120.96(17) . . ? C13 C12 C7 118.06(15) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14C 120.0 . . ? C12 C14 H14A 120.0 . . ? H14C C14 H14A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.117 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.028