# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/454 data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 N O3' _chemical_formula_weight 341.44 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.120(9) _cell_length_b 11.511(9) _cell_length_c 11.189(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.329(10) _cell_angle_gamma 90.00 _cell_volume 2064(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.099 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3274 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3218 _reflns_number_gt 2683 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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^)+(0.1278P)^2^+0.1574P] 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 SHELXL _refine_ls_extinction_coef 0.061(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(19) _refine_ls_number_reflns 3218 _refine_ls_number_parameters 231 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1734 _refine_ls_wR_factor_gt 0.1629 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.051 _refine_ls_shift/su_mean 0.007 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 N1 N 0.21578(12) 0.0400(2) 0.69506(17) 0.0425(5) Uani 1 d . . . C2 C 0.16159(15) -0.0436(2) 0.6246(2) 0.0426(6) Uani 1 d . . . H2 H 0.1943 -0.1132 0.6113 0.051 Uiso 1 calc R . . C3 C 0.12995(18) 0.0088(3) 0.5028(2) 0.0548(7) Uani 1 d . . . H31 H 0.0924 -0.0456 0.4582 0.066 Uiso 1 calc R . . H32 H 0.0989 0.0792 0.5149 0.066 Uiso 1 calc R . . O4 O 0.19857(14) 0.0355(2) 0.43398(16) 0.0670(7) Uani 1 d . . . C5 C 0.2627(2) 0.0944(3) 0.4950(3) 0.0642(9) Uani 1 d . . . C6 C 0.25463(19) 0.1295(3) 0.6240(2) 0.0544(7) Uani 1 d . . . H6 H 0.3115 0.1412 0.6631 0.065 Uiso 1 calc R . . C7 C 0.27303(16) -0.0169(3) 0.7916(2) 0.0478(6) Uani 1 d . . . H7 H 0.2391 -0.0733 0.8303 0.057 Uiso 1 calc R . . C10 C 0.3043(2) 0.0728(3) 0.8899(2) 0.0633(9) Uani 1 d . . . H10A H 0.3578 0.1022 0.8714 0.076 Uiso 1 calc R . . H10B H 0.2656 0.1377 0.8837 0.076 Uiso 1 calc R . . C11 C 0.3146(2) 0.0316(4) 1.0215(2) 0.0676(9) Uani 1 d . . . C111 C 0.3488(4) 0.1335(6) 1.1005(4) 0.119(2) Uani 1 d . . . H11A H 0.3138 0.2003 1.0835 0.142 Uiso 1 calc R . . H11B H 0.4045 0.1512 1.0837 0.142 Uiso 1 calc R . . H11C H 0.3493 0.1128 1.1837 0.142 Uiso 1 calc R . . C112 C 0.2275(4) 0.0047(7) 1.0583(4) 0.142(3) Uani 1 d . . . H11D H 0.2042 -0.0607 1.0130 0.170 Uiso 1 calc R . . H11E H 0.1920 0.0710 1.0422 0.170 Uiso 1 calc R . . H11F H 0.2320 -0.0132 1.1426 0.170 Uiso 1 calc R . . C113 C 0.3647(5) -0.0799(7) 1.0417(5) 0.154(3) Uani 1 d . . . H11G H 0.3641 -0.1049 1.1235 0.184 Uiso 1 calc R . . H11H H 0.4213 -0.0662 1.0260 0.184 Uiso 1 calc R . . H11I H 0.3405 -0.1391 0.9884 0.184 Uiso 1 calc R . . C21 C 0.34234(18) -0.0854(3) 0.7442(2) 0.0557(7) Uani 1 d . . . O22 O 0.41006(15) -0.0223(3) 0.7135(2) 0.0803(7) Uani 1 d . . . C23 C 0.4638(3) -0.1016(6) 0.6720(5) 0.1026(16) Uani 1 d . . . H23 H 0.5143 -0.0822 0.6442 0.123 Uiso 1 calc R . . C24 C 0.4348(3) -0.2088(5) 0.6766(4) 0.1008(17) Uani 1 d . . . H24 H 0.4607 -0.2766 0.6548 0.121 Uiso 1 calc R . . C25 C 0.3547(3) -0.1990(4) 0.7223(4) 0.0829(11) Uani 1 d . . . H25 H 0.3184 -0.2596 0.7345 0.100 Uiso 1 calc R . . C31 C 0.08654(14) -0.0791(2) 0.6900(2) 0.0411(6) Uani 1 d . . . C32 C 0.05005(16) -0.1878(2) 0.6678(3) 0.0512(7) Uani 1 d . . . H32 H 0.0727 -0.2396 0.6165 0.061 Uiso 1 calc R . . C33 C -0.0209(2) -0.2193(3) 0.7227(4) 0.0716(10) Uani 1 d . . . H33 H -0.0452 -0.2919 0.7076 0.086 Uiso 1 calc R . . C34 C -0.0545(2) -0.1435(4) 0.7985(4) 0.0767(10) Uani 1 d . . . H34 H -0.1014 -0.1647 0.8347 0.092 Uiso 1 calc R . . C35 C -0.0189(2) -0.0355(4) 0.8213(3) 0.0772(10) Uani 1 d . . . H35 H -0.0419 0.0156 0.8729 0.093 Uiso 1 calc R . . C36 C 0.05154(18) -0.0029(3) 0.7671(3) 0.0599(8) Uani 1 d . . . H36 H 0.0752 0.0700 0.7825 0.072 Uiso 1 calc R . . O51 O 0.3226(2) 0.1176(4) 0.4421(3) 0.1071(12) Uani 1 d . . . C61 C 0.2104(3) 0.2477(3) 0.6248(4) 0.0817(11) Uani 1 d . . . H61A H 0.1575 0.2432 0.5763 0.098 Uiso 1 calc R . . H61B H 0.2443 0.3060 0.5927 0.098 Uiso 1 calc R . . H61C H 0.2017 0.2677 0.7057 0.098 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 N1 0.0410(12) 0.0459(12) 0.0403(10) 0.0018(9) 0.0039(7) -0.0105(9) C2 0.0367(13) 0.0471(14) 0.0436(13) -0.0044(11) 0.0027(9) -0.0067(10) C3 0.0553(16) 0.069(2) 0.0399(13) 0.0015(12) 0.0040(10) -0.0161(13) O4 0.0781(15) 0.0815(15) 0.0433(9) -0.0005(11) 0.0150(9) -0.0230(12) C5 0.067(2) 0.073(2) 0.0552(16) 0.0095(15) 0.0167(13) -0.0192(16) C6 0.0584(17) 0.0529(17) 0.0517(14) 0.0071(13) 0.0046(11) -0.0182(13) C7 0.0519(15) 0.0513(16) 0.0390(12) 0.0037(11) 0.0001(10) -0.0155(12) C10 0.076(2) 0.071(2) 0.0417(14) -0.0063(13) 0.0020(12) -0.0293(16) C11 0.0661(19) 0.095(3) 0.0403(13) -0.0027(16) -0.0003(12) -0.0158(18) C111 0.149(4) 0.149(5) 0.056(2) -0.033(3) 0.001(2) -0.055(4) C112 0.152(5) 0.211(8) 0.071(2) -0.018(3) 0.046(3) -0.088(5) C113 0.200(7) 0.175(7) 0.075(3) 0.000(4) -0.038(4) 0.057(6) C21 0.0523(17) 0.0591(18) 0.0519(14) 0.0002(13) -0.0110(11) -0.0049(13) O22 0.0551(14) 0.0898(18) 0.0963(17) -0.0082(14) 0.0102(10) -0.0065(12) C23 0.054(2) 0.136(5) 0.117(3) -0.037(3) 0.005(2) 0.014(2) C24 0.080(3) 0.118(4) 0.099(3) -0.032(3) -0.015(2) 0.037(3) C25 0.089(3) 0.073(3) 0.082(2) -0.0134(19) -0.0170(19) 0.0049(19) C31 0.0310(12) 0.0476(14) 0.0442(12) 0.0055(11) 0.0014(9) -0.0019(9) C32 0.0398(14) 0.0435(15) 0.0703(18) 0.0078(13) 0.0064(11) -0.0005(11) C33 0.0428(18) 0.061(2) 0.112(3) 0.0197(19) 0.0107(16) -0.0101(13) C34 0.052(2) 0.093(3) 0.090(2) 0.018(2) 0.0279(16) -0.0061(17) C35 0.061(2) 0.106(3) 0.069(2) -0.015(2) 0.0244(15) -0.0023(19) C36 0.0488(16) 0.067(2) 0.0652(16) -0.0120(15) 0.0138(12) -0.0074(13) O51 0.091(2) 0.156(3) 0.0797(16) 0.0144(18) 0.0353(14) -0.048(2) C61 0.128(3) 0.0463(19) 0.069(2) 0.0070(16) 0.002(2) -0.0100(19) _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 C2 1.469(3) . ? N1 C6 1.481(3) . ? N1 C7 1.492(3) . ? C2 C3 1.526(4) . ? C2 C31 1.537(3) . ? C3 O4 1.449(3) . ? O4 C5 1.356(4) . ? C5 O51 1.217(4) . ? C5 C6 1.519(4) . ? C6 C61 1.537(5) . ? C7 C21 1.510(4) . ? C7 C10 1.552(4) . ? C10 C11 1.539(4) . ? C11 C113 1.520(8) . ? C11 C111 1.534(6) . ? C11 C112 1.538(6) . ? C21 C25 1.348(6) . ? C21 O22 1.386(4) . ? O22 C23 1.374(5) . ? C23 C24 1.323(9) . ? C24 C25 1.446(6) . ? C31 C32 1.393(4) . ? C31 C36 1.393(4) . ? C32 C33 1.404(4) . ? C33 C34 1.369(6) . ? C34 C35 1.380(6) . ? C35 C36 1.396(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 C2 N1 C6 115.40(19) . . ? C2 N1 C7 112.6(2) . . ? C6 N1 C7 115.4(2) . . ? N1 C2 C3 110.0(2) . . ? N1 C2 C31 111.83(19) . . ? C3 C2 C31 109.1(2) . . ? O4 C3 C2 111.0(2) . . ? C5 O4 C3 115.0(2) . . ? O51 C5 O4 117.8(3) . . ? O51 C5 C6 124.1(3) . . ? O4 C5 C6 118.1(2) . . ? N1 C6 C5 114.3(2) . . ? N1 C6 C61 112.9(3) . . ? C5 C6 C61 109.2(3) . . ? N1 C7 C21 113.4(2) . . ? N1 C7 C10 110.3(3) . . ? C21 C7 C10 113.7(2) . . ? C11 C10 C7 117.8(3) . . ? C113 C11 C111 114.2(4) . . ? C113 C11 C112 106.0(6) . . ? C111 C11 C112 106.3(4) . . ? C113 C11 C10 113.7(3) . . ? C111 C11 C10 108.1(3) . . ? C112 C11 C10 108.2(3) . . ? C25 C21 O22 109.1(3) . . ? C25 C21 C7 134.4(3) . . ? O22 C21 C7 116.5(3) . . ? C23 O22 C21 106.1(4) . . ? C24 C23 O22 111.6(5) . . ? C23 C24 C25 105.9(4) . . ? C21 C25 C24 107.2(4) . . ? C32 C31 C36 119.0(2) . . ? C32 C31 C2 119.6(2) . . ? C36 C31 C2 121.4(2) . . ? C31 C32 C33 120.1(3) . . ? C34 C33 C32 120.2(3) . . ? C33 C34 C35 120.2(3) . . ? C34 C35 C36 120.2(3) . . ? C35 C36 C31 120.3(3) . . ? _refine_diff_density_max 0.346 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.059 _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1990) SHELX86, Acta Cryst. A46 467-480. Sheldrick, G.M. (1993) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (1994) PLATON-94 program, Utrecht University, The Netherlands ;