Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_ak0104 _database_code_CSD 189673 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Kirby, Anthony J.' 'Bilenko, Vitaliy A.' 'Davies, John E.' 'Komarov, Igor V.' 'Rawson, Jeremy M.' _publ_contact_author_name 'Prof Anthony J. Kirby' _publ_contact_author_address ; Department of Chemistry University of Cambridge University Chemical Laboratory Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email AJK1@CAM.AC.UK _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H25 N O2' _chemical_formula_sum 'C13 H25 N O2' _chemical_formula_weight 227.34 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' 'N' 'N' 0.0061 0.0033 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.5697(18) _cell_length_b 8.2191(4) _cell_length_c 13.2975(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.489(3) _cell_angle_gamma 90.00 _cell_volume 2564.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7448 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.854 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Crystals obtained by sublimation in vacuo. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method 'fine slice omega/phi scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7716 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0527 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2895 _reflns_number_gt 2104 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution ; SIR92: A.Altomare, G.Cascarano, C.Giacovazzo, A.Guagliardi, M.C.Burla, G.Ploidori, M.Camalli. J.Appl.Cryst. (1994) 27, 435-435 ; _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ; XP (Sheldrick, 1993) CAMERON (Watkin et al. 1996) ; _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^)+(0.0653P)^2^+1.3875P] 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 2895 _refine_ls_number_parameters 160 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1439 _refine_ls_wR_factor_gt 0.1286 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 N1 N 0.31178(5) 0.16327(15) 0.85331(9) 0.0232(3) Uani 1 1 d . . . O1 O 0.31180(5) -0.10267(13) 0.93098(9) 0.0348(3) Uani 1 1 d . . . C2 C 0.32476(7) -0.03261(17) 0.84749(12) 0.0271(4) Uani 1 1 d . . . H2 H 0.3003 -0.0799 0.7892 0.040(5) Uiso 1 1 calc R . . C3 C 0.38784(7) -0.04443(18) 0.82516(12) 0.0259(4) Uani 1 1 d . . . C4 C 0.42538(7) 0.03178(18) 0.91322(12) 0.0253(4) Uani 1 1 d . . . H4A H 0.4660 0.0183 0.9018 0.0315(14) Uiso 1 1 calc R . . H4B H 0.4188 -0.0251 0.9767 0.0315(14) Uiso 1 1 calc R . . C5 C 0.41200(6) 0.21341(18) 0.92360(11) 0.0239(3) Uani 1 1 d . . . C6 C 0.42261(7) 0.29970(19) 0.82483(12) 0.0266(4) Uani 1 1 d . . . H6A H 0.4146 0.4174 0.8310 0.0315(14) Uiso 1 1 calc R . . H6B H 0.4631 0.2871 0.8124 0.0315(14) Uiso 1 1 calc R . . C7 C 0.38463(7) 0.22903(19) 0.73565(12) 0.0270(4) Uani 1 1 d . . . C8 C 0.32273(7) 0.24795(19) 0.75762(12) 0.0265(4) Uani 1 1 d . . . H8A H 0.3137 0.3650 0.7633 0.0315(14) Uiso 1 1 calc R . . H8B H 0.2975 0.2021 0.7008 0.0315(14) Uiso 1 1 calc R . . C9 C 0.34898(6) 0.23205(18) 0.94040(11) 0.0237(3) Uani 1 1 d . . . H9A H 0.3413 0.1749 1.0032 0.0315(14) Uiso 1 1 calc R . . H9B H 0.3400 0.3487 0.9484 0.0315(14) Uiso 1 1 calc R . . C10 C 0.39701(7) 0.04622(19) 0.72732(12) 0.0291(4) Uani 1 1 d . . . H10A H 0.3717 -0.0006 0.6710 0.0315(14) Uiso 1 1 calc R . . H10B H 0.4369 0.0309 0.7117 0.0315(14) Uiso 1 1 calc R . . C11 C 0.40193(8) -0.2251(2) 0.81493(15) 0.0377(4) Uani 1 1 d . . . H11A H 0.3951 -0.2820 0.8774 0.0448(15) Uiso 1 1 calc R . . H11B H 0.4420 -0.2371 0.8026 0.0448(15) Uiso 1 1 calc R . . H11C H 0.3777 -0.2719 0.7583 0.0448(15) Uiso 1 1 calc R . . C12 C 0.44826(7) 0.2887(2) 1.01293(13) 0.0332(4) Uani 1 1 d . . . H12A H 0.4392 0.2363 1.0757 0.0448(15) Uiso 1 1 calc R . . H12B H 0.4401 0.4054 1.0162 0.0448(15) Uiso 1 1 calc R . . H12C H 0.4887 0.2726 1.0043 0.0448(15) Uiso 1 1 calc R . . C13 C 0.39252(8) 0.3176(2) 0.63723(13) 0.0386(4) Uani 1 1 d . . . H13A H 0.3674 0.2693 0.5822 0.0448(15) Uiso 1 1 calc R . . H13B H 0.4322 0.3075 0.6221 0.0448(15) Uiso 1 1 calc R . . H13C H 0.3830 0.4328 0.6441 0.0448(15) Uiso 1 1 calc R . . C14 C 0.25062(7) 0.1835(2) 0.86885(13) 0.0301(4) Uani 1 1 d . . . H14A H 0.2270 0.1432 0.8094 0.0448(15) Uiso 1 1 calc R . . H14B H 0.2425 0.2989 0.8789 0.0448(15) Uiso 1 1 calc R . . H14C H 0.2420 0.1216 0.9285 0.0448(15) Uiso 1 1 calc R . . O2W O 0.22978(6) -0.08599(15) 1.07183(10) 0.0380(3) Uani 1 1 d D . . H2W H 0.2552(10) -0.091(3) 1.0277(17) 0.068(5) Uiso 1 1 d D . . H1W H 0.2145(10) -0.182(3) 1.0720(17) 0.068(5) Uiso 1 1 d 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 N1 0.0216(7) 0.0236(6) 0.0248(7) 0.0005(5) 0.0044(5) 0.0005(5) O1 0.0368(7) 0.0253(6) 0.0441(7) 0.0063(5) 0.0137(6) -0.0029(5) C2 0.0282(8) 0.0187(7) 0.0347(9) -0.0022(6) 0.0044(7) -0.0011(6) C3 0.0275(8) 0.0219(8) 0.0285(8) -0.0033(6) 0.0042(6) 0.0021(6) C4 0.0238(8) 0.0257(8) 0.0268(8) 0.0013(6) 0.0049(6) 0.0033(6) C5 0.0243(8) 0.0233(7) 0.0242(8) -0.0014(6) 0.0030(6) -0.0003(6) C6 0.0263(8) 0.0243(8) 0.0301(9) 0.0009(6) 0.0075(7) -0.0018(6) C7 0.0281(8) 0.0301(8) 0.0233(8) 0.0032(6) 0.0058(6) 0.0007(6) C8 0.0270(8) 0.0275(8) 0.0249(8) 0.0033(6) 0.0017(6) 0.0008(6) C9 0.0262(8) 0.0233(7) 0.0223(8) -0.0019(6) 0.0055(6) 0.0019(6) C10 0.0279(8) 0.0342(9) 0.0259(8) -0.0057(7) 0.0058(7) 0.0016(6) C11 0.0409(10) 0.0257(8) 0.0472(11) -0.0062(8) 0.0076(8) 0.0042(7) C12 0.0325(9) 0.0365(9) 0.0303(9) -0.0050(7) 0.0008(7) -0.0023(7) C13 0.0394(10) 0.0476(11) 0.0299(9) 0.0085(8) 0.0087(8) 0.0009(8) C14 0.0224(8) 0.0316(9) 0.0370(9) 0.0011(7) 0.0062(7) 0.0025(6) O2W 0.0462(8) 0.0266(6) 0.0423(7) -0.0013(5) 0.0100(6) -0.0027(6) _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 N1 C14 1.4850(19) . ? N1 C8 1.4943(19) . ? N1 C9 1.4951(19) . ? N1 C2 1.6420(18) . ? O1 C2 1.3124(19) . ? C2 C3 1.547(2) . ? C2 H2 1.0000 . ? C3 C11 1.530(2) . ? C3 C10 1.532(2) . ? C3 C4 1.532(2) . ? C4 C5 1.535(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C12 1.526(2) . ? C5 C9 1.531(2) . ? C5 C6 1.534(2) . ? C6 C7 1.530(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.523(2) . ? C7 C13 1.524(2) . ? C7 C10 1.537(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O2W H2W 0.88(2) . ? O2W H1W 0.87(2) . ? 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 C14 N1 C8 108.39(12) . . ? C14 N1 C9 110.80(11) . . ? C8 N1 C9 110.31(11) . . ? C14 N1 C2 107.69(11) . . ? C8 N1 C2 111.62(11) . . ? C9 N1 C2 108.01(11) . . ? O1 C2 C3 116.14(13) . . ? O1 C2 N1 109.32(12) . . ? C3 C2 N1 104.92(11) . . ? O1 C2 H2 108.7 . . ? C3 C2 H2 108.7 . . ? N1 C2 H2 108.7 . . ? C11 C3 C10 110.30(13) . . ? C11 C3 C4 110.50(13) . . ? C10 C3 C4 109.39(13) . . ? C11 C3 C2 107.38(13) . . ? C10 C3 C2 110.41(13) . . ? C4 C3 C2 108.84(12) . . ? C3 C4 C5 110.96(12) . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C12 C5 C9 108.95(12) . . ? C12 C5 C6 110.73(12) . . ? C9 C5 C6 108.57(12) . . ? C12 C5 C4 111.08(13) . . ? C9 C5 C4 108.73(12) . . ? C6 C5 C4 108.72(12) . . ? C7 C6 C5 110.91(12) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C13 108.28(13) . . ? C8 C7 C6 108.22(12) . . ? C13 C7 C6 111.95(13) . . ? C8 C7 C10 107.80(12) . . ? C13 C7 C10 111.43(13) . . ? C6 C7 C10 109.03(13) . . ? N1 C8 C7 111.25(12) . . ? N1 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? N1 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N1 C9 C5 110.77(11) . . ? N1 C9 H9A 109.5 . . ? C5 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C3 C10 C7 111.78(12) . . ? C3 C10 H10A 109.3 . . ? C7 C10 H10A 109.3 . . ? C3 C10 H10B 109.3 . . ? C7 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C5 C12 H12A 109.5 . . ? C5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? H2W O2W H1W 105.8(18) . . ? 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 C14 N1 C2 O1 -57.97(16) . . . . ? C8 N1 C2 O1 -176.83(12) . . . . ? C9 N1 C2 O1 61.74(15) . . . . ? C14 N1 C2 C3 176.82(12) . . . . ? C8 N1 C2 C3 57.96(15) . . . . ? C9 N1 C2 C3 -63.47(14) . . . . ? O1 C2 C3 C11 61.25(17) . . . . ? N1 C2 C3 C11 -177.94(13) . . . . ? O1 C2 C3 C10 -178.47(13) . . . . ? N1 C2 C3 C10 -57.66(15) . . . . ? O1 C2 C3 C4 -58.39(16) . . . . ? N1 C2 C3 C4 62.42(14) . . . . ? C11 C3 C4 C5 179.48(12) . . . . ? C10 C3 C4 C5 57.87(16) . . . . ? C2 C3 C4 C5 -62.84(15) . . . . ? C3 C4 C5 C12 178.55(12) . . . . ? C3 C4 C5 C9 58.67(16) . . . . ? C3 C4 C5 C6 -59.36(16) . . . . ? C12 C5 C6 C7 -177.79(12) . . . . ? C9 C5 C6 C7 -58.21(16) . . . . ? C4 C5 C6 C7 59.92(16) . . . . ? C5 C6 C7 C8 58.31(16) . . . . ? C5 C6 C7 C13 177.56(13) . . . . ? C5 C6 C7 C10 -58.68(16) . . . . ? C14 N1 C8 C7 -178.77(12) . . . . ? C9 N1 C8 C7 59.76(15) . . . . ? C2 N1 C8 C7 -60.33(16) . . . . ? C13 C7 C8 N1 179.79(13) . . . . ? C6 C7 C8 N1 -58.66(16) . . . . ? C10 C7 C8 N1 59.12(16) . . . . ? C14 N1 C9 C5 -179.18(12) . . . . ? C8 N1 C9 C5 -59.15(15) . . . . ? C2 N1 C9 C5 63.09(14) . . . . ? C12 C5 C9 N1 178.68(12) . . . . ? C6 C5 C9 N1 58.00(15) . . . . ? C4 C5 C9 N1 -60.13(15) . . . . ? C11 C3 C10 C7 -178.64(13) . . . . ? C4 C3 C10 C7 -56.91(17) . . . . ? C2 C3 C10 C7 62.85(17) . . . . ? C8 C7 C10 C3 -60.00(17) . . . . ? C13 C7 C10 C3 -178.68(13) . . . . ? C6 C7 C10 C3 57.26(16) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.298 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.076