Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_jpc73 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H25 N O' _chemical_formula_sum 'C17 H25 N O' _chemical_formula_weight 259.38 _chemical_absolute_configuration syn 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.2621(11) _cell_length_b 5.2062(5) _cell_length_c 14.3092(14) _cell_angle_alpha 90.00 _cell_angle_beta 109.094(5) _cell_angle_gamma 90.00 _cell_volume 792.83(13) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8340 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 33.98 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.087 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type none _exptl_special_details ; The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker Nonius FR591 rotating anode generator ; _diffrn_radiation_monochromator ; graphite model mounted in "parallel" mode ; _diffrn_measurement_device_type ; Mach3 kappa-type 4-circle goniostat. ; _diffrn_radiation_detector 'ApexII camera' _diffrn_measurement_method 'rotation images' _diffrn_detector_area_resol_mean ; 120 microns ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 33635 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0089 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1743 _reflns_number_gt 1679 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; APEX 2 software, Bruker Nonius 2004 ; _computing_cell_refinement ; APEX 2 software, Bruker Nonius 2004 ; _computing_data_reduction ; SAINT - Bruker Integration program embedded in APEX 2 software, Bruker Nonius 2004 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III Version 1.08 (Farrugia, 2005)' _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; The structure solved in spacegroup P21. All hydrogen atoms could be located in the Fourier difference map but in the final stages of refinement hydrogen atoms bonded to carbon were placed in calculated positions and refined using a riding model. C-H distances: aromatic, 0.95\A; methyl, 0.98\A; olefinic, 0.95\A; methylene, 0.99\A; methine, 1.00\A. H8 attached to N8 was positioned in a planar configuration and the distance N8-H8 refined to 0.85(3)\A. All Uiso(H) values were constrained to be 1.2 times Ueq of the parent atom. All Uiso(H) values were constrained to be 1.2 times Ueq of the parent atom. In the absence of significant anomalous scattering effects, the absolute stereochemistry could not be determined from the X-ray data and Friedel pairs were merged. The model was assigned on the basis of the known stereochemistry of the starting reagent. C.Kilner 21 July 2005 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^)+(0.0353P)^2^+0.2173P] 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 1743 _refine_ls_number_parameters 178 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0797 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.72953(14) 0.9912(4) 0.98770(12) 0.0224(4) Uani 1 1 d . . . C2 C 0.64639(15) 1.1780(4) 1.00110(13) 0.0275(4) Uani 1 1 d . . . H2 H 0.6189 1.3133 0.9544 0.033 Uiso 1 1 calc R . . C3 C 0.60391(16) 1.1665(4) 1.08247(14) 0.0316(4) Uani 1 1 d . . . H3 H 0.5470 1.2925 1.0905 0.038 Uiso 1 1 calc R . . C4 C 0.64508(17) 0.9696(4) 1.15200(14) 0.0324(5) Uani 1 1 d . . . H4 H 0.6157 0.9606 1.2070 0.039 Uiso 1 1 calc R . . C5 C 0.72911(18) 0.7873(4) 1.14038(13) 0.0337(5) Uani 1 1 d . . . H5 H 0.7582 0.6549 1.1881 0.040 Uiso 1 1 calc R . . C6 C 0.77114(16) 0.7979(4) 1.05836(13) 0.0277(4) Uani 1 1 d . . . H6 H 0.8285 0.6722 1.0509 0.033 Uiso 1 1 calc R . . C7 C 0.77441(15) 1.0024(4) 0.89760(12) 0.0242(4) Uani 1 1 d . . . H7 H 0.8148 0.8346 0.8922 0.029 Uiso 1 1 calc R . . C8 C 0.87153(16) 1.2171(4) 0.90807(14) 0.0309(4) Uani 1 1 d . . . H8A H 0.9415 1.1934 0.9697 0.037 Uiso 1 1 calc R . . H8B H 0.8319 1.3841 0.9093 0.037 Uiso 1 1 calc R . . H8C H 0.9031 1.2109 0.8519 0.037 Uiso 1 1 calc R . . C9 C 0.59542(17) 0.8477(4) 0.75493(13) 0.0246(4) Uani 1 1 d . . . C10 C 0.48173(17) 0.9313(4) 0.67195(13) 0.0290(4) Uani 1 1 d . . . H10 H 0.4642 1.1096 0.6622 0.035 Uiso 1 1 calc R . . C11 C 0.40445(17) 0.7640(4) 0.61141(13) 0.0313(4) Uani 1 1 d . . . H11 H 0.4267 0.5877 0.6214 0.038 Uiso 1 1 calc R . . C12 C 0.28418(18) 0.8269(5) 0.52789(13) 0.0352(5) Uani 1 1 d . . . H12 H 0.2708 1.0169 0.5266 0.042 Uiso 1 1 calc R . . C13 C 0.2946(2) 0.7448(7) 0.42851(15) 0.0527(7) Uani 1 1 d . . . H13A H 0.2152 0.7808 0.3759 0.063 Uiso 1 1 calc R . . H13B H 0.3125 0.5603 0.4299 0.063 Uiso 1 1 calc R . . H13C H 0.3627 0.8404 0.4159 0.063 Uiso 1 1 calc R . . C14 C 0.17155(17) 0.6945(4) 0.54659(13) 0.0333(4) Uani 1 1 d . . . H14A H 0.0973 0.7094 0.4862 0.040 Uiso 1 1 calc R . . H14B H 0.1907 0.5095 0.5589 0.040 Uiso 1 1 calc R . . C15 C 0.13863(17) 0.8063(4) 0.63389(13) 0.0321(4) Uani 1 1 d . . . H15A H 0.2133 0.7940 0.6941 0.038 Uiso 1 1 calc R . . H15B H 0.1182 0.9906 0.6211 0.038 Uiso 1 1 calc R . . C16 C 0.02827(18) 0.6722(5) 0.65338(14) 0.0380(5) Uani 1 1 d . . . H16A H -0.0468 0.6861 0.5935 0.046 Uiso 1 1 calc R . . H16B H 0.0483 0.4875 0.6656 0.046 Uiso 1 1 calc R . . C17 C -0.0030(2) 0.7836(6) 0.74136(17) 0.0514(6) Uani 1 1 d . . . H17A H -0.0792 0.7016 0.7460 0.062 Uiso 1 1 calc R . . H17B H -0.0169 0.9690 0.7322 0.062 Uiso 1 1 calc R . . H17C H 0.0670 0.7516 0.8023 0.062 Uiso 1 1 calc R . . N8 N 0.66767(15) 1.0432(3) 0.80587(11) 0.0261(3) Uani 1 1 d . . . H8 H 0.644(2) 1.195(6) 0.7880(15) 0.031 Uiso 1 1 d . . . O9 O 0.62122(13) 0.6181(3) 0.77617(11) 0.0319(3) Uani 1 1 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 C1 0.0185(7) 0.0200(9) 0.0256(8) -0.0034(7) 0.0030(6) -0.0028(7) C2 0.0244(8) 0.0228(10) 0.0335(9) 0.0011(8) 0.0068(7) 0.0016(8) C3 0.0258(8) 0.0293(11) 0.0413(10) -0.0065(9) 0.0129(7) -0.0015(8) C4 0.0339(9) 0.0354(12) 0.0294(9) -0.0051(9) 0.0124(7) -0.0098(9) C5 0.0399(10) 0.0295(11) 0.0282(9) 0.0034(9) 0.0062(8) -0.0019(9) C6 0.0263(8) 0.0222(10) 0.0319(9) 0.0001(8) 0.0058(7) 0.0028(8) C7 0.0227(8) 0.0196(9) 0.0291(8) -0.0009(8) 0.0070(6) 0.0018(8) C8 0.0276(9) 0.0281(10) 0.0387(9) -0.0025(9) 0.0133(7) -0.0029(9) C9 0.0276(8) 0.0227(9) 0.0262(8) -0.0009(8) 0.0125(7) -0.0019(8) C10 0.0346(9) 0.0239(9) 0.0275(8) 0.0036(8) 0.0090(7) 0.0006(8) C11 0.0343(9) 0.0297(11) 0.0293(9) 0.0002(8) 0.0098(7) -0.0012(9) C12 0.0369(10) 0.0362(11) 0.0280(9) 0.0004(9) 0.0045(7) -0.0014(10) C13 0.0467(12) 0.075(2) 0.0378(11) -0.0064(13) 0.0158(9) 0.0018(14) C14 0.0323(9) 0.0325(11) 0.0294(9) -0.0025(9) 0.0023(7) -0.0039(9) C15 0.0317(9) 0.0262(10) 0.0325(9) -0.0014(8) 0.0025(7) 0.0023(8) C16 0.0357(10) 0.0346(12) 0.0395(10) -0.0002(10) 0.0065(8) -0.0003(10) C17 0.0510(13) 0.0521(16) 0.0563(13) -0.0017(13) 0.0247(11) 0.0022(12) N8 0.0314(8) 0.0183(8) 0.0266(7) 0.0019(7) 0.0065(6) 0.0012(7) O9 0.0334(7) 0.0197(7) 0.0390(7) -0.0001(6) 0.0070(6) 0.0002(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 C1 C6 1.394(3) . ? C1 C2 1.406(2) . ? C1 C7 1.532(2) . ? C2 C3 1.397(3) . ? C2 H2 0.9500 . ? C3 C4 1.398(3) . ? C3 H3 0.9500 . ? C4 C5 1.388(3) . ? C4 H4 0.9500 . ? C5 C6 1.403(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N8 1.477(2) . ? C7 C8 1.537(3) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 O9 1.244(3) . ? C9 N8 1.357(3) . ? C9 C10 1.498(3) . ? C10 C11 1.332(3) . ? C10 H10 0.9500 . ? C11 C12 1.520(2) . ? C11 H11 0.9500 . ? C12 C13 1.526(3) . ? C12 C14 1.542(3) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.529(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.529(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.528(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N8 H8 0.85(3) . ? 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 118.76(16) . . ? C6 C1 C7 120.84(16) . . ? C2 C1 C7 120.40(16) . . ? C3 C2 C1 120.58(18) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 120.02(18) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 119.78(17) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.20(18) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 120.65(17) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? N8 C7 C1 110.90(13) . . ? N8 C7 C8 109.18(15) . . ? C1 C7 C8 111.47(15) . . ? N8 C7 H7 108.4 . . ? C1 C7 H7 108.4 . . ? C8 C7 H7 108.4 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O9 C9 N8 122.58(18) . . ? O9 C9 C10 122.93(18) . . ? N8 C9 C10 114.49(17) . . ? C11 C10 C9 122.20(19) . . ? C11 C10 H10 118.9 . . ? C9 C10 H10 118.9 . . ? C10 C11 C12 126.5(2) . . ? C10 C11 H11 116.7 . . ? C12 C11 H11 116.7 . . ? C11 C12 C13 110.61(17) . . ? C11 C12 C14 109.84(16) . . ? C13 C12 C14 110.80(18) . . ? C11 C12 H12 108.5 . . ? C13 C12 H12 108.5 . . ? C14 C12 H12 108.5 . . ? 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 . . ? C15 C14 C12 113.88(17) . . ? C15 C14 H14A 108.8 . . ? C12 C14 H14A 108.8 . . ? C15 C14 H14B 108.8 . . ? C12 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 113.84(17) . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? C14 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 113.42(19) . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C9 N8 C7 122.69(17) . . ? C9 N8 H8 117.7(15) . . ? C7 N8 H8 119.1(15) . . ? 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 -1.6(3) . . . . ? C7 C1 C2 C3 179.14(17) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C2 C1 C6 C5 1.1(3) . . . . ? C7 C1 C6 C5 -179.54(17) . . . . ? C4 C5 C6 C1 0.1(3) . . . . ? C6 C1 C7 N8 133.12(17) . . . . ? C2 C1 C7 N8 -47.6(2) . . . . ? C6 C1 C7 C8 -105.00(19) . . . . ? C2 C1 C7 C8 74.30(19) . . . . ? O9 C9 C10 C11 -4.1(3) . . . . ? N8 C9 C10 C11 176.45(17) . . . . ? C9 C10 C11 C12 177.34(16) . . . . ? C10 C11 C12 C13 117.5(2) . . . . ? C10 C11 C12 C14 -119.9(2) . . . . ? C11 C12 C14 C15 69.2(2) . . . . ? C13 C12 C14 C15 -168.33(19) . . . . ? C12 C14 C15 C16 -179.10(17) . . . . ? C14 C15 C16 C17 179.43(19) . . . . ? O9 C9 N8 C7 -7.3(3) . . . . ? C10 C9 N8 C7 172.10(15) . . . . ? C1 C7 N8 C9 -84.6(2) . . . . ? C8 C7 N8 C9 152.22(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.301 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.028