Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_1 _database_code_CSD 163541 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Drew, M.' 'Harwood, L.' 'Hughes, David J.' 'Vickers, Richard J.' _publ_contact_author_name 'Prof L Harwood' _publ_contact_author_address ; Prof L Harwood Department of CHemistry Reading University Whiteknights Reading RG6 6AD UNITED KINGDOM ; _publ_contact_author_email 'L.M.HARWOOD@READING.AC.UK' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 N2 O2' _chemical_formula_weight 258.31 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.599(12) _cell_length_b 6.542(8) _cell_length_c 12.017(14) _cell_angle_alpha 90.00 _cell_angle_beta 99.615(10) _cell_angle_gamma 90.00 _cell_volume 744.0(16) _cell_formula_units_Z 2 _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 ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _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 293(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 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1631 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 26.02 _reflns_number_total 1584 _reflns_number_gt 1112 _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^)+(0.1443P)^2^+1.1687P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 6(5) _refine_ls_number_reflns 1584 _refine_ls_number_parameters 174 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.2227 _refine_ls_wR_factor_gt 0.1937 _refine_ls_goodness_of_fit_ref 0.717 _refine_ls_restrained_S_all 0.717 _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 N1 N 0.3222(6) 0.1074(7) 0.2312(3) 0.0473(12) Uani 1 d . . . C2 C 0.4648(11) 0.0477(12) 0.2388(5) 0.076(3) Uani 1 d . . . H2A H 0.5202 0.1696 0.2316 0.092 Uiso 1 calc R . . H2B H 0.4719 -0.0386 0.1744 0.092 Uiso 1 calc R . . C3 C 0.5335(15) -0.0653(15) 0.3449(6) 0.091(3) Uani 1 d . . . O4 O 0.4667(9) -0.0720(9) 0.4324(4) 0.094(2) Uani 1 d . . . C5 C 0.3284(10) 0.0198(12) 0.4252(5) 0.072(2) Uani 1 d . . . H5A H 0.3183 0.0712 0.4992 0.086 Uiso 1 calc R . . H5B H 0.2574 -0.0852 0.4049 0.086 Uiso 1 calc R . . C6 C 0.2999(8) 0.1922(9) 0.3412(3) 0.0545(16) Uani 1 d . . . H6 H 0.3657 0.3052 0.3635 0.065 Uiso 1 calc R . . O31 O 0.6448(10) -0.1513(12) 0.3502(5) 0.106(2) Uani 1 d . . . C11 C 0.2750(8) 0.2419(10) 0.1340(4) 0.0590(17) Uani 1 d . . . H11 H 0.1784 0.2862 0.1377 0.071 Uiso 1 calc R . . C12 C 0.3671(14) 0.4279(15) 0.1427(7) 0.098(3) Uani 1 d . . . N13 N 0.4454(16) 0.5624(17) 0.1508(9) 0.140(4) Uani 1 d . . . C14 C 0.2747(10) 0.1398(13) 0.0198(4) 0.077(2) Uani 1 d . . . H14 H 0.3707 0.0928 0.0161 0.092 Uiso 1 calc R . . C15 C 0.181(2) -0.0379(19) 0.0096(7) 0.132(5) Uani 1 d . . . H15A H 0.0875 0.0046 0.0183 0.158 Uiso 1 calc R . . H15B H 0.2156 -0.1357 0.0671 0.158 Uiso 1 calc R . . H15C H 0.1776 -0.0991 -0.0634 0.158 Uiso 1 calc R . . C16 C 0.2305(13) 0.2907(18) -0.0753(5) 0.101(3) Uani 1 d . . . H16A H 0.2425 0.2295 -0.1457 0.121 Uiso 1 calc R . . H16B H 0.2879 0.4113 -0.0625 0.121 Uiso 1 calc R . . H16C H 0.1330 0.3267 -0.0779 0.121 Uiso 1 calc R . . C61 C 0.1485(7) 0.2638(9) 0.3379(3) 0.0495(15) Uani 1 d . . . C62 C 0.1235(11) 0.4542(11) 0.3803(5) 0.074(2) Uani 1 d . . . H62 H 0.1981 0.5399 0.4093 0.089 Uiso 1 calc R . . C63 C -0.0196(14) 0.5161(13) 0.3785(6) 0.093(4) Uani 1 d . . . H63 H -0.0369 0.6430 0.4084 0.112 Uiso 1 calc R . . C64 C -0.1295(12) 0.3992(15) 0.3358(6) 0.089(3) Uani 1 d . . . H64 H -0.2219 0.4461 0.3307 0.106 Uiso 1 calc R . . C65 C -0.1006(11) 0.2048(15) 0.2993(6) 0.086(3) Uani 1 d . . . H65 H -0.1748 0.1147 0.2761 0.103 Uiso 1 calc R . . C66 C 0.0329(10) 0.1446(11) 0.2970(5) 0.068(2) Uani 1 d . . . H66 H 0.0478 0.0174 0.2665 0.081 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 0.058(4) 0.037(2) 0.048(2) -0.0074(17) 0.0155(19) -0.005(2) C2 0.106(9) 0.067(4) 0.063(3) 0.002(3) 0.031(4) 0.019(4) C3 0.118(12) 0.089(6) 0.071(4) -0.007(4) 0.028(5) -0.004(6) O4 0.124(7) 0.099(4) 0.061(3) 0.015(2) 0.018(3) 0.016(4) C5 0.083(7) 0.081(5) 0.053(3) 0.001(3) 0.018(3) -0.005(4) C6 0.077(5) 0.052(3) 0.034(2) -0.007(2) 0.007(2) -0.012(3) O31 0.109(8) 0.118(5) 0.093(4) 0.013(3) 0.017(3) 0.026(5) C11 0.069(5) 0.065(4) 0.044(2) 0.005(2) 0.012(2) -0.010(3) C12 0.125(11) 0.083(6) 0.090(5) 0.021(4) 0.028(5) -0.006(6) N13 0.147(15) 0.101(7) 0.175(9) 0.027(7) 0.037(7) -0.010(8) C14 0.084(7) 0.096(6) 0.053(3) 0.001(3) 0.018(3) 0.019(5) C15 0.214(17) 0.104(7) 0.069(4) -0.013(4) 0.002(6) -0.020(8) C16 0.108(10) 0.131(8) 0.066(4) 0.021(4) 0.021(4) 0.023(7) C61 0.056(5) 0.056(3) 0.038(2) -0.002(2) 0.014(2) -0.003(3) C62 0.098(8) 0.065(4) 0.061(3) -0.010(3) 0.021(3) 0.006(4) C63 0.135(12) 0.074(5) 0.077(4) -0.009(4) 0.038(5) 0.028(6) C64 0.082(8) 0.112(7) 0.076(4) -0.014(4) 0.027(4) 0.009(6) C65 0.075(8) 0.115(7) 0.072(4) -0.010(4) 0.025(3) -0.013(5) C66 0.071(7) 0.077(5) 0.060(3) -0.008(3) 0.024(3) -0.005(4) _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 1.411(11) . ? N1 C11 1.472(8) . ? N1 C6 1.482(6) . ? C2 C3 1.525(13) . ? C3 O31 1.199(14) . ? C3 O4 1.321(11) . ? O4 C5 1.447(11) . ? C5 C6 1.508(9) . ? C6 C61 1.521(10) . ? C11 C12 1.497(14) . ? C11 C14 1.526(8) . ? C12 N13 1.151(16) . ? C14 C15 1.463(16) . ? C14 C16 1.516(12) . ? C61 C66 1.377(11) . ? C61 C62 1.382(9) . ? C62 C63 1.430(15) . ? C63 C64 1.334(15) . ? C64 C65 1.389(12) . ? C65 C66 1.346(12) . ? 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 C11 112.5(5) . . ? C2 N1 C6 109.2(5) . . ? C11 N1 C6 114.4(5) . . ? N1 C2 C3 117.8(6) . . ? O31 C3 O4 119.2(9) . . ? O31 C3 C2 121.9(7) . . ? O4 C3 C2 118.8(11) . . ? C3 O4 C5 120.1(7) . . ? O4 C5 C6 114.4(5) . . ? N1 C6 C5 106.3(5) . . ? N1 C6 C61 111.8(4) . . ? C5 C6 C61 108.3(5) . . ? N1 C11 C12 109.3(6) . . ? N1 C11 C14 114.0(6) . . ? C12 C11 C14 109.3(6) . . ? N13 C12 C11 175.5(14) . . ? C15 C14 C16 111.3(9) . . ? C15 C14 C11 109.4(6) . . ? C16 C14 C11 110.6(7) . . ? C66 C61 C62 117.6(7) . . ? C66 C61 C6 123.0(6) . . ? C62 C61 C6 119.4(6) . . ? C61 C62 C63 118.4(8) . . ? C64 C63 C62 122.7(8) . . ? C63 C64 C65 117.4(10) . . ? C66 C65 C64 121.0(9) . . ? C65 C66 C61 122.7(7) . . ? _refine_diff_density_max 0.151 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.035 _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 ;