# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Wood, Mark E.' _publ_contact_author_email M.E.Wood@exeter.ac.uk _publ_section_title ; Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generation of alpha-aminoalkyl radicals ; _publ_author_name M.E.Wood # Attachment '- 01src782.cif' data_01src782 _database_code_depnum_ccdc_archive 'CCDC 291244' #TrackingRef '- 01src782.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H30 N4 O2' _chemical_formula_weight 478.58 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9276(2) _cell_length_b 14.5482(4) _cell_length_c 10.1033(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.5700(10) _cell_angle_gamma 90.00 _cell_volume 1236.42(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5757 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9822 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 8639 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2801 _reflns_number_gt 2232 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'Sheldrick, G.M. (2008). Acta Cryst. A64, 112-1' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _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^ > 2\s(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^)+(0.0638P)^2^+0.1837P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2801 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1050 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 0.71021(16) 0.10773(9) 0.72916(14) 0.0316(3) Uani 1 1 d . . . H1A H 0.8236 0.1259 0.7607 0.038 Uiso 1 1 calc R . . H1B H 0.6783 0.0969 0.8127 0.038 Uiso 1 1 calc R . . C2 C 0.60752(15) 0.18057(8) 0.63599(13) 0.0276(3) Uani 1 1 d . . . H2A H 0.5677 0.2249 0.6907 0.033 Uiso 1 1 calc R . . H2B H 0.6656 0.2142 0.5830 0.033 Uiso 1 1 calc R . . N1 N 0.47855(11) 0.12519(7) 0.54275(10) 0.0218(2) Uani 1 1 d . . . C4 C 0.62997(13) 0.05533(8) 0.39575(13) 0.0216(3) Uani 1 1 d . . . C5 C 0.79399(15) 0.06506(9) 0.43097(14) 0.0297(3) Uani 1 1 d . . . H5 H 0.8605 0.0613 0.5264 0.036 Uiso 1 1 calc R . . C6 C 0.85997(16) 0.08015(10) 0.32704(16) 0.0358(3) Uani 1 1 d . . . H6 H 0.9721 0.0868 0.3548 0.043 Uiso 1 1 calc R . . C7 C 0.61886(15) 0.07748(9) 0.15702(14) 0.0275(3) Uani 1 1 d . . . H7 H 0.5556 0.0815 0.0606 0.033 Uiso 1 1 calc R . . C8 C 0.54147(14) 0.06323(8) 0.25335(13) 0.0241(3) Uani 1 1 d . . . H8 H 0.4288 0.0589 0.2226 0.029 Uiso 1 1 calc R . . C9 C 0.37214(15) 0.17772(8) 0.42505(13) 0.0247(3) Uani 1 1 d . . . H9A H 0.3036 0.1349 0.3543 0.030 Uiso 1 1 calc R . . H9B H 0.4359 0.2136 0.3798 0.030 Uiso 1 1 calc R . . C10 C 0.26918(13) 0.24229(8) 0.47500(12) 0.0224(3) Uani 1 1 d . . . C11 C 0.18620(15) 0.21028(9) 0.56016(13) 0.0269(3) Uani 1 1 d . . . H11 H 0.1990 0.1483 0.5918 0.032 Uiso 1 1 calc R . . C12 C 0.08456(15) 0.26828(9) 0.59937(14) 0.0302(3) Uani 1 1 d . . . H12 H 0.0271 0.2454 0.6563 0.036 Uiso 1 1 calc R . . C13 C 0.06662(15) 0.35872(9) 0.55624(14) 0.0310(3) Uani 1 1 d . . . H13 H -0.0027 0.3982 0.5835 0.037 Uiso 1 1 calc R . . C14 C 0.15020(15) 0.39168(9) 0.47291(14) 0.0297(3) Uani 1 1 d . . . H14 H 0.1390 0.4541 0.4435 0.036 Uiso 1 1 calc R . . C15 C 0.25062(14) 0.33355(8) 0.43210(13) 0.0249(3) Uani 1 1 d . . . H15 H 0.3070 0.3565 0.3743 0.030 Uiso 1 1 calc R . . C3 C 0.55689(13) 0.04250(8) 0.51291(12) 0.0199(3) Uani 1 1 d . . . N2 N 0.77632(13) 0.08605(8) 0.19010(12) 0.0326(3) Uani 1 1 d . . . O1 O 0.68343(9) 0.02671(6) 0.64162(8) 0.0234(2) 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 0.0314(7) 0.0298(7) 0.0279(7) -0.0053(5) 0.0024(6) -0.0040(5) C2 0.0300(7) 0.0223(6) 0.0291(7) -0.0050(5) 0.0081(6) -0.0023(5) N1 0.0231(5) 0.0194(5) 0.0217(5) -0.0016(4) 0.0061(4) 0.0035(4) C4 0.0229(6) 0.0172(5) 0.0259(6) -0.0003(5) 0.0098(5) 0.0020(4) C5 0.0243(6) 0.0347(7) 0.0305(7) 0.0003(6) 0.0097(5) 0.0003(5) C6 0.0238(7) 0.0461(8) 0.0404(8) -0.0009(6) 0.0146(6) -0.0024(6) C7 0.0316(7) 0.0261(6) 0.0275(7) -0.0009(5) 0.0132(6) 0.0015(5) C8 0.0239(6) 0.0228(6) 0.0266(6) 0.0003(5) 0.0098(5) 0.0019(5) C9 0.0305(7) 0.0217(6) 0.0238(6) 0.0033(5) 0.0117(5) 0.0077(5) C10 0.0204(6) 0.0231(6) 0.0220(6) -0.0009(5) 0.0049(5) 0.0035(4) C11 0.0302(7) 0.0240(6) 0.0272(6) 0.0014(5) 0.0105(5) 0.0023(5) C12 0.0275(7) 0.0384(8) 0.0274(7) -0.0008(6) 0.0129(5) 0.0024(5) C13 0.0279(7) 0.0347(7) 0.0300(7) -0.0030(6) 0.0094(6) 0.0118(5) C14 0.0314(7) 0.0231(6) 0.0328(7) 0.0012(5) 0.0082(6) 0.0085(5) C15 0.0240(6) 0.0244(6) 0.0260(6) 0.0011(5) 0.0080(5) 0.0022(5) C3 0.0178(6) 0.0196(6) 0.0204(6) 0.0006(4) 0.0040(5) 0.0030(4) N2 0.0335(6) 0.0346(6) 0.0361(7) -0.0010(5) 0.0201(5) -0.0009(5) O1 0.0202(4) 0.0245(5) 0.0213(4) 0.0001(3) 0.0016(3) 0.0014(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.4447(15) . ? C1 C2 1.5072(18) . ? C2 N1 1.4614(15) . ? N1 C9 1.4642(15) . ? N1 C3 1.4726(15) . ? C4 C5 1.3934(17) . ? C4 C8 1.3949(17) . ? C4 C3 1.5425(16) . ? C5 C6 1.3828(19) . ? C6 N2 1.3368(19) . ? C7 N2 1.3373(17) . ? C7 C8 1.3850(17) . ? C9 C10 1.5142(16) . ? C10 C15 1.3892(17) . ? C10 C11 1.3903(17) . ? C11 C12 1.3903(17) . ? C12 C13 1.3785(19) . ? C13 C14 1.3844(19) . ? C14 C15 1.3916(17) . ? C3 O1 1.4268(13) . ? C3 C3 1.566(2) 3_656 ? 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 O1 C1 C2 104.48(10) . . ? N1 C2 C1 101.42(10) . . ? C2 N1 C9 113.11(10) . . ? C2 N1 C3 104.88(9) . . ? C9 N1 C3 118.92(9) . . ? C5 C4 C8 116.02(11) . . ? C5 C4 C3 119.65(10) . . ? C8 C4 C3 124.22(10) . . ? C6 C5 C4 120.04(12) . . ? N2 C6 C5 124.31(12) . . ? N2 C7 C8 124.63(12) . . ? C7 C8 C4 119.58(11) . . ? N1 C9 C10 110.75(9) . . ? C15 C10 C11 118.72(11) . . ? C15 C10 C9 120.75(10) . . ? C11 C10 C9 120.48(11) . . ? C10 C11 C12 120.47(12) . . ? C13 C12 C11 120.46(12) . . ? C12 C13 C14 119.59(11) . . ? C13 C14 C15 120.10(12) . . ? C10 C15 C14 120.65(11) . . ? O1 C3 N1 103.31(9) . . ? O1 C3 C4 108.03(8) . . ? N1 C3 C4 114.21(9) . . ? O1 C3 C3 107.23(11) . 3_656 ? N1 C3 C3 110.69(11) . 3_656 ? C4 C3 C3 112.66(12) . 3_656 ? C6 N2 C7 115.39(11) . . ? C3 O1 C1 110.17(8) . . ? 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 O1 C1 C2 N1 29.37(12) . . . . ? C1 C2 N1 C9 -170.82(10) . . . . ? C1 C2 N1 C3 -39.72(12) . . . . ? C8 C4 C5 C6 -0.97(18) . . . . ? C3 C4 C5 C6 -177.50(12) . . . . ? C4 C5 C6 N2 -0.3(2) . . . . ? N2 C7 C8 C4 -1.14(19) . . . . ? C5 C4 C8 C7 1.62(16) . . . . ? C3 C4 C8 C7 177.98(11) . . . . ? C2 N1 C9 C10 -72.35(12) . . . . ? C3 N1 C9 C10 163.96(10) . . . . ? N1 C9 C10 C15 133.01(12) . . . . ? N1 C9 C10 C11 -49.65(15) . . . . ? C15 C10 C11 C12 1.11(18) . . . . ? C9 C10 C11 C12 -176.28(11) . . . . ? C10 C11 C12 C13 -1.05(19) . . . . ? C11 C12 C13 C14 0.2(2) . . . . ? C12 C13 C14 C15 0.54(19) . . . . ? C11 C10 C15 C14 -0.36(18) . . . . ? C9 C10 C15 C14 177.03(11) . . . . ? C13 C14 C15 C10 -0.46(19) . . . . ? C2 N1 C3 O1 35.02(11) . . . . ? C9 N1 C3 O1 162.67(9) . . . . ? C2 N1 C3 C4 -82.06(11) . . . . ? C9 N1 C3 C4 45.59(14) . . . . ? C2 N1 C3 C3 149.52(12) . . . 3_656 ? C9 N1 C3 C3 -82.83(15) . . . 3_656 ? C5 C4 C3 O1 -10.29(14) . . . . ? C8 C4 C3 O1 173.48(10) . . . . ? C5 C4 C3 N1 104.04(12) . . . . ? C8 C4 C3 N1 -72.19(14) . . . . ? C5 C4 C3 C3 -128.55(13) . . . 3_656 ? C8 C4 C3 C3 55.22(16) . . . 3_656 ? C5 C6 N2 C7 0.9(2) . . . . ? C8 C7 N2 C6 -0.14(19) . . . . ? N1 C3 O1 C1 -15.86(12) . . . . ? C4 C3 O1 C1 105.50(11) . . . . ? C3 C3 O1 C1 -132.82(12) 3_656 . . . ? C2 C1 O1 C3 -8.50(13) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.256 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.091