# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Mark E. Wood' _publ_contact_author_address ; School of Biosciences (formerly Chemistry) University of Exeter Geoffrey Pope Building Stocker Road Exeter Devon EX4 4QD UNITED KINGDOM ; _publ_contact_author_email M.E.WOOD@EXETER.AC.UK _publ_section_title ; A general route to protected quaternary ?-amino acids from ?-amino alcohols via a stereocontrolled radical approach ; loop_ _publ_author_name 'Mark E. Wood' 'Peter N. Horton' 'Michael B. Hursthouse' 'Mark E. Light' 'Mark J. Penny' ; J.S.Steere ; data_1a _database_code_depnum_ccdc_archive 'CCDC 602435' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 I N O2' _chemical_formula_weight 373.22 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' I I -0.4742 1.8119 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.7729(7) _cell_length_b 7.4551(4) _cell_length_c 17.0731(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.236(4) _cell_angle_gamma 90.00 _cell_volume 1552.75(14) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3658 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 2.061 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5961 _exptl_absorpt_correction_T_max 0.9221 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _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 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15953 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6846 _reflns_number_gt 5682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _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^)+(0.0333P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.0023(3) _chemical_absolute_configuration ad _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 0.005(18) _refine_ls_number_reflns 6846 _refine_ls_number_parameters 352 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0728 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.062 _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 C2 C 0.8869(4) 0.4860(6) 0.7785(3) 0.0248(10) Uani 1 1 d . . . H2 H 0.8196 0.5542 0.7484 0.030 Uiso 1 1 calc R . . C4 C 0.9728(4) 0.2924(6) 0.7010(3) 0.0251(11) Uani 1 1 d . . . H4 H 0.9690 0.2889 0.6417 0.030 Uiso 1 1 calc R . . C5 C 0.8690(4) 0.2132(7) 0.7132(3) 0.0335(12) Uani 1 1 d . . . H5A H 0.8048 0.2371 0.6651 0.040 Uiso 1 1 calc R . . H5B H 0.8764 0.0820 0.7223 0.040 Uiso 1 1 calc R . . C6 C 1.0767(4) 0.1988(7) 0.7527(3) 0.0360(12) Uani 1 1 d . . . H6A H 1.1410 0.2688 0.7512 0.054 Uiso 1 1 calc R . . H6B H 1.0810 0.0787 0.7306 0.054 Uiso 1 1 calc R . . H6C H 1.0747 0.1889 0.8095 0.054 Uiso 1 1 calc R . . C7 C 0.9710(4) 0.6217(6) 0.6785(3) 0.0268(11) Uani 1 1 d . . . C8 C 1.0335(4) 0.5837(5) 0.6181(3) 0.0257(11) Uani 1 1 d . . . C9 C 0.9771(4) 0.5535(7) 0.5361(3) 0.0302(11) Uani 1 1 d . . . C10 C 1.0338(5) 0.5200(6) 0.4799(3) 0.0357(13) Uani 1 1 d . . . H10 H 0.9951 0.4956 0.4242 0.043 Uiso 1 1 calc R . . C11 C 1.1456(5) 0.5224(7) 0.5051(3) 0.0390(13) Uani 1 1 d . . . H11 H 1.1847 0.5028 0.4664 0.047 Uiso 1 1 calc R . . C12 C 1.2027(4) 0.5534(7) 0.5871(3) 0.0362(12) Uani 1 1 d . . . H12 H 1.2806 0.5519 0.6026 0.043 Uiso 1 1 calc R . . C13 C 1.1522(4) 0.5866(5) 0.6479(3) 0.0326(12) Uani 1 1 d U . . H13 H 1.1919 0.6090 0.7036 0.039 Uiso 1 1 calc R . . C14 C 0.9315(4) 0.5625(6) 0.8659(3) 0.0286(11) Uani 1 1 d . . . C15 C 0.9426(5) 0.7659(7) 0.8628(3) 0.0386(13) Uani 1 1 d . . . H15A H 0.9671 0.8137 0.9187 0.058 Uiso 1 1 calc R . . H15B H 0.8715 0.8184 0.8334 0.058 Uiso 1 1 calc R . . H15C H 0.9964 0.7962 0.8342 0.058 Uiso 1 1 calc R . . C16 C 0.8457(5) 0.5167(8) 0.9097(3) 0.0432(14) Uani 1 1 d . . . H16A H 0.8370 0.3862 0.9110 0.065 Uiso 1 1 calc R . . H16B H 0.7754 0.5716 0.8801 0.065 Uiso 1 1 calc R . . H16C H 0.8700 0.5631 0.9659 0.065 Uiso 1 1 calc R . . C17 C 1.0397(4) 0.4773(7) 0.9116(3) 0.0339(12) Uani 1 1 d . . . H17A H 1.0935 0.5006 0.8821 0.051 Uiso 1 1 calc R . . H17B H 1.0299 0.3476 0.9155 0.051 Uiso 1 1 calc R . . H17C H 1.0661 0.5285 0.9669 0.051 Uiso 1 1 calc R . . N3 N 0.9633(3) 0.4792(4) 0.7271(2) 0.0214(8) Uani 1 1 d . . . O1 O 0.8583(3) 0.3033(4) 0.7848(2) 0.0330(8) Uani 1 1 d . . . O7 O 0.9342(3) 0.7706(4) 0.6857(2) 0.0353(9) Uani 1 1 d . . . I9 I 0.80522(3) 0.54065(4) 0.494965(18) 0.03789(11) Uani 1 1 d . . . C22 C 0.5393(4) 0.3855(5) 0.3347(2) 0.0199(9) Uani 1 1 d . . . H22 H 0.6074 0.3110 0.3500 0.024 Uiso 1 1 calc R . . C24 C 0.5069(4) 0.6008(5) 0.2230(3) 0.0222(10) Uani 1 1 d . . . H24 H 0.5375 0.6124 0.1757 0.027 Uiso 1 1 calc R . . C25 C 0.5921(4) 0.6617(6) 0.3017(2) 0.0253(10) Uani 1 1 d . . . H25A H 0.6672 0.6332 0.3002 0.030 Uiso 1 1 calc R . . H25B H 0.5867 0.7924 0.3100 0.030 Uiso 1 1 calc R . . C26 C 0.3997(4) 0.6982(6) 0.2045(3) 0.0310(11) Uani 1 1 d . . . H26A H 0.3462 0.6407 0.1579 0.046 Uiso 1 1 calc R . . H26B H 0.4099 0.8233 0.1908 0.046 Uiso 1 1 calc R . . H26C H 0.3728 0.6942 0.2526 0.046 Uiso 1 1 calc R . . C27 C 0.5219(4) 0.2758(6) 0.1956(3) 0.0224(10) Uani 1 1 d . . . C28 C 0.4895(4) 0.3160(5) 0.1066(2) 0.0198(9) Uani 1 1 d . . . C29 C 0.5665(3) 0.3418(6) 0.0638(2) 0.0230(9) Uani 1 1 d . . . C30 C 0.5336(4) 0.3729(6) -0.0209(3) 0.0290(11) Uani 1 1 d . . . H30 H 0.5866 0.3912 -0.0491 0.035 Uiso 1 1 calc R . . C31 C 0.4231(4) 0.3765(6) -0.0628(3) 0.0298(11) Uani 1 1 d . . . H31 H 0.3995 0.3983 -0.1202 0.036 Uiso 1 1 calc R . . C32 C 0.3470(4) 0.3483(7) -0.0211(3) 0.0325(11) Uani 1 1 d . . . H32 H 0.2712 0.3470 -0.0506 0.039 Uiso 1 1 calc R . . C33 C 0.3793(4) 0.3218(6) 0.0628(3) 0.0252(10) Uani 1 1 d . . . H33 H 0.3256 0.3075 0.0907 0.030 Uiso 1 1 calc R . . C34 C 0.4568(4) 0.3050(5) 0.3739(2) 0.0246(10) Uani 1 1 d . . . C35 C 0.4273(4) 0.1129(6) 0.3442(3) 0.0277(11) Uani 1 1 d . . . H35A H 0.3760 0.0629 0.3712 0.042 Uiso 1 1 calc R . . H35B H 0.4939 0.0396 0.3575 0.042 Uiso 1 1 calc R . . H35C H 0.3930 0.1132 0.2847 0.042 Uiso 1 1 calc R . . C36 C 0.3525(4) 0.4160(6) 0.3568(3) 0.0312(11) Uani 1 1 d . . . H36A H 0.3709 0.5378 0.3780 0.047 Uiso 1 1 calc R . . H36B H 0.3029 0.3607 0.3839 0.047 Uiso 1 1 calc R . . H36C H 0.3167 0.4210 0.2976 0.047 Uiso 1 1 calc R . . C37 C 0.5136(4) 0.2993(6) 0.4670(3) 0.0311(12) Uani 1 1 d . . . H37A H 0.5348 0.4211 0.4871 0.047 Uiso 1 1 calc R . . H37B H 0.5791 0.2236 0.4784 0.047 Uiso 1 1 calc R . . H37C H 0.4630 0.2497 0.4947 0.047 Uiso 1 1 calc R . . N23 N 0.5009(3) 0.4078(5) 0.2442(2) 0.0210(8) Uani 1 1 d . . . O21 O 0.5659(3) 0.5637(4) 0.36464(17) 0.0241(7) Uani 1 1 d . . . O27 O 0.5576(3) 0.1281(4) 0.22249(18) 0.0290(8) Uani 1 1 d . . . I29 I 0.73415(2) 0.34831(4) 0.126218(19) 0.03631(11) 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 C2 0.022(3) 0.026(3) 0.030(2) 0.0022(18) 0.012(2) -0.0024(19) C4 0.030(3) 0.017(2) 0.028(2) -0.0006(18) 0.008(2) -0.0005(19) C5 0.036(3) 0.022(2) 0.039(3) -0.005(2) 0.005(2) -0.002(2) C6 0.038(3) 0.030(3) 0.038(3) 0.006(2) 0.008(2) 0.008(2) C7 0.033(3) 0.024(2) 0.020(2) -0.0026(19) 0.002(2) -0.003(2) C8 0.037(3) 0.013(2) 0.027(2) -0.0009(17) 0.009(2) -0.0015(19) C9 0.043(3) 0.013(2) 0.032(2) -0.002(2) 0.007(2) 0.002(2) C10 0.063(4) 0.017(3) 0.033(3) 0.002(2) 0.024(3) 0.000(3) C11 0.062(4) 0.017(2) 0.053(3) -0.002(2) 0.040(3) -0.006(3) C12 0.040(3) 0.022(2) 0.054(3) 0.003(3) 0.024(3) -0.004(3) C13 0.044(3) 0.013(2) 0.058(3) 0.0161(19) 0.041(2) 0.0102(18) C14 0.029(3) 0.033(3) 0.030(2) 0.002(2) 0.018(2) 0.004(2) C15 0.055(4) 0.034(3) 0.025(2) -0.007(2) 0.010(2) -0.002(3) C16 0.042(3) 0.049(3) 0.046(3) -0.001(3) 0.024(3) 0.001(3) C17 0.032(3) 0.043(3) 0.023(2) 0.007(2) 0.003(2) 0.000(2) N3 0.026(2) 0.0170(17) 0.0212(18) 0.0010(14) 0.0069(16) -0.0005(15) O1 0.033(2) 0.0280(18) 0.0414(19) -0.0064(15) 0.0164(15) -0.0081(15) O7 0.063(3) 0.0136(16) 0.0313(18) -0.0006(13) 0.0178(18) 0.0091(16) I9 0.0424(2) 0.02676(16) 0.03453(18) -0.00145(14) -0.00395(14) -0.00018(16) C22 0.026(2) 0.021(2) 0.0133(19) 0.0012(17) 0.0066(17) -0.0003(18) C24 0.028(3) 0.014(2) 0.027(2) 0.0065(17) 0.011(2) 0.0032(18) C25 0.031(3) 0.021(2) 0.026(2) -0.0016(19) 0.012(2) -0.005(2) C26 0.041(3) 0.020(2) 0.031(2) 0.003(2) 0.010(2) 0.005(2) C27 0.027(3) 0.018(2) 0.025(2) -0.0011(18) 0.013(2) -0.0011(19) C28 0.028(2) 0.012(2) 0.022(2) -0.0021(17) 0.0098(18) -0.0003(18) C29 0.021(2) 0.019(2) 0.029(2) -0.001(2) 0.0067(18) -0.001(2) C30 0.047(3) 0.021(2) 0.024(2) -0.001(2) 0.017(2) 0.001(2) C31 0.047(3) 0.020(2) 0.019(2) 0.0017(19) 0.005(2) 0.007(2) C32 0.035(3) 0.025(2) 0.031(2) 0.002(2) -0.001(2) 0.001(3) C33 0.025(2) 0.021(2) 0.030(2) -0.0002(19) 0.0091(19) -0.003(2) C34 0.031(3) 0.023(2) 0.020(2) -0.0009(18) 0.0077(19) 0.0017(19) C35 0.034(3) 0.028(2) 0.021(2) -0.0041(19) 0.007(2) -0.006(2) C36 0.036(3) 0.033(3) 0.031(3) 0.007(2) 0.018(2) 0.007(2) C37 0.046(3) 0.029(3) 0.021(2) 0.0042(19) 0.014(2) 0.000(2) N23 0.028(2) 0.0202(18) 0.0149(17) 0.0014(14) 0.0062(15) 0.0040(16) O21 0.0350(19) 0.0189(16) 0.0187(14) -0.0035(12) 0.0084(13) -0.0042(14) O27 0.045(2) 0.0233(17) 0.0235(16) 0.0017(14) 0.0175(15) 0.0103(16) I29 0.02643(18) 0.03945(19) 0.04325(19) 0.00194(15) 0.01064(14) -0.00235(15) _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 C2 O1 1.423(5) . ? C2 N3 1.495(6) . ? C2 C14 1.540(6) . ? C2 H2 1.0000 . ? C4 N3 1.477(5) . ? C4 C5 1.521(7) . ? C4 C6 1.527(7) . ? C4 H4 1.0000 . ? C5 O1 1.437(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 O7 1.225(5) . ? C7 N3 1.370(6) . ? C7 C8 1.506(7) . ? C8 C9 1.390(6) . ? C8 C13 1.450(7) . ? C9 C10 1.386(7) . ? C9 I9 2.099(5) . ? C10 C11 1.363(8) . ? C10 H10 0.9500 . ? C11 C12 1.394(7) . ? C11 H11 0.9500 . ? C12 C13 1.396(7) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C17 1.512(7) . ? C14 C15 1.526(7) . ? C14 C16 1.536(7) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C22 O21 1.427(5) . ? C22 N23 1.487(5) . ? C22 C34 1.528(6) . ? C22 H22 1.0000 . ? C24 N23 1.492(5) . ? C24 C26 1.499(6) . ? C24 C25 1.526(6) . ? C24 H24 1.0000 . ? C25 O21 1.419(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 O27 1.228(5) . ? C27 N23 1.363(5) . ? C27 C28 1.483(6) . ? C28 C33 1.385(6) . ? C28 C29 1.400(6) . ? C29 C30 1.401(6) . ? C29 I29 2.091(4) . ? C30 C31 1.380(7) . ? C30 H30 0.9500 . ? C31 C32 1.380(7) . ? C31 H31 0.9500 . ? C32 C33 1.383(6) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 C36 1.522(6) . ? C34 C35 1.529(6) . ? C34 C37 1.539(6) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? 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 C2 N3 103.8(3) . . ? O1 C2 C14 108.1(4) . . ? N3 C2 C14 117.6(4) . . ? O1 C2 H2 109.0 . . ? N3 C2 H2 109.0 . . ? C14 C2 H2 109.0 . . ? N3 C4 C5 99.9(4) . . ? N3 C4 C6 113.1(4) . . ? C5 C4 C6 112.8(4) . . ? N3 C4 H4 110.2 . . ? C5 C4 H4 110.2 . . ? C6 C4 H4 110.2 . . ? O1 C5 C4 104.0(4) . . ? O1 C5 H5A 111.0 . . ? C4 C5 H5A 111.0 . . ? O1 C5 H5B 111.0 . . ? C4 C5 H5B 111.0 . . ? H5A C5 H5B 109.0 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O7 C7 N3 122.9(4) . . ? O7 C7 C8 122.4(4) . . ? N3 C7 C8 114.6(4) . . ? C9 C8 C13 122.2(4) . . ? C9 C8 C7 119.9(4) . . ? C13 C8 C7 117.9(4) . . ? C10 C9 C8 120.3(5) . . ? C10 C9 I9 118.0(3) . . ? C8 C9 I9 121.5(4) . . ? C11 C10 C9 119.6(5) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.4(5) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 123.8(5) . . ? C11 C12 H12 118.1 . . ? C13 C12 H12 118.1 . . ? C12 C13 C8 113.7(5) . . ? C12 C13 H13 123.2 . . ? C8 C13 H13 123.2 . . ? C17 C14 C15 110.8(4) . . ? C17 C14 C16 109.3(4) . . ? C15 C14 C16 109.0(4) . . ? C17 C14 C2 111.3(4) . . ? C15 C14 C2 110.2(4) . . ? C16 C14 C2 106.1(4) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C7 N3 C4 121.5(3) . . ? C7 N3 C2 120.4(4) . . ? C4 N3 C2 109.6(3) . . ? C2 O1 C5 107.0(3) . . ? O21 C22 N23 103.8(3) . . ? O21 C22 C34 109.4(3) . . ? N23 C22 C34 116.2(3) . . ? O21 C22 H22 109.1 . . ? N23 C22 H22 109.1 . . ? C34 C22 H22 109.1 . . ? N23 C24 C26 114.2(4) . . ? N23 C24 C25 98.5(3) . . ? C26 C24 C25 114.2(4) . . ? N23 C24 H24 109.8 . . ? C26 C24 H24 109.8 . . ? C25 C24 H24 109.8 . . ? O21 C25 C24 104.3(3) . . ? O21 C25 H25A 110.9 . . ? C24 C25 H25A 110.9 . . ? O21 C25 H25B 110.9 . . ? C24 C25 H25B 110.9 . . ? H25A C25 H25B 108.9 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O27 C27 N23 122.6(4) . . ? O27 C27 C28 121.6(4) . . ? N23 C27 C28 115.6(4) . . ? C33 C28 C29 118.3(4) . . ? C33 C28 C27 119.2(4) . . ? C29 C28 C27 122.5(4) . . ? C28 C29 C30 121.3(4) . . ? C28 C29 I29 120.6(3) . . ? C30 C29 I29 118.1(3) . . ? C31 C30 C29 119.1(4) . . ? C31 C30 H30 120.5 . . ? C29 C30 H30 120.5 . . ? C32 C31 C30 119.8(4) . . ? C32 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C31 C32 C33 121.1(4) . . ? C31 C32 H32 119.4 . . ? C33 C32 H32 119.4 . . ? C32 C33 C28 120.4(4) . . ? C32 C33 H33 119.8 . . ? C28 C33 H33 119.8 . . ? C36 C34 C22 112.3(4) . . ? C36 C34 C35 109.3(4) . . ? C22 C34 C35 110.9(4) . . ? C36 C34 C37 109.3(4) . . ? C22 C34 C37 106.7(4) . . ? C35 C34 C37 108.2(3) . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C34 C37 H37A 109.5 . . ? C34 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C34 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C27 N23 C22 119.3(3) . . ? C27 N23 C24 121.1(3) . . ? C22 N23 C24 109.6(3) . . ? C25 O21 C22 107.0(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.515 _refine_diff_density_min -0.756 _refine_diff_density_rms 0.099 #===END data_3a _database_code_depnum_ccdc_archive 'CCDC 602436' _chemical_absolute_configuration syn _chemical_compound_source 'ME Wood' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H24 N2 O2' _chemical_formula_weight 300.39 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.6733(6) _cell_length_b 13.630(2) _cell_length_c 15.8871(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1661.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10893 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description 'Cut Block' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9693 _exptl_absorpt_correction_T_max 0.9768 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 9450 reflections reduced R(int) from 0.0820 to 0.0351 Ratio of minimum to maximum apparent transmission: 0.777690 The given Tmin and Tmax were generated using the SHELX SIZE command ; _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 CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9839 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1696 _reflns_number_gt 1564 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0391P)^2^+0.2987P] 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 SHELXL _refine_ls_extinction_coef 0.032(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1696 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0751 _refine_ls_wR_factor_gt 0.0723 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 C2 C 0.7697(2) 0.31417(14) 0.37063(11) 0.0191(4) Uani 1 1 d . . . H2 H 0.8619 0.2653 0.3854 0.023 Uiso 1 1 calc R . . C4 C 0.6626(2) 0.44624(14) 0.46177(12) 0.0200(4) Uani 1 1 d . . . C5 C 0.5232(2) 0.37004(15) 0.43784(12) 0.0242(5) Uani 1 1 d . . . H5A H 0.4489 0.3549 0.4871 0.029 Uiso 1 1 calc R . . H5B H 0.4481 0.3958 0.3922 0.029 Uiso 1 1 calc R . . C6 C 0.6031(3) 0.54798(15) 0.43514(13) 0.0265(5) Uani 1 1 d . . . H6A H 0.6842 0.5972 0.4573 0.040 Uiso 1 1 calc R . . H6B H 0.4861 0.5605 0.4574 0.040 Uiso 1 1 calc R . . H6C H 0.6005 0.5519 0.3736 0.040 Uiso 1 1 calc R . . C7 C 0.9874(2) 0.42152(14) 0.42956(11) 0.0189(4) Uani 1 1 d . . . C8 C 1.0469(2) 0.50945(14) 0.47819(12) 0.0204(4) Uani 1 1 d . . . C9 C 1.1456(2) 0.49285(15) 0.55062(12) 0.0232(5) Uani 1 1 d . . . H9 H 1.1657 0.4277 0.5694 0.028 Uiso 1 1 calc R . . C10 C 1.2140(2) 0.57088(15) 0.59500(12) 0.0266(5) Uani 1 1 d . . . H10 H 1.2787 0.5595 0.6450 0.032 Uiso 1 1 calc R . . C11 C 1.1883(3) 0.66587(15) 0.56657(13) 0.0294(5) Uani 1 1 d . . . H11 H 1.2349 0.7197 0.5971 0.035 Uiso 1 1 calc R . . C12 C 1.0947(3) 0.68196(15) 0.49366(12) 0.0301(5) Uani 1 1 d . . . H12 H 1.0792 0.7471 0.4737 0.036 Uiso 1 1 calc R . . C13 C 1.0231(3) 0.60446(14) 0.44930(12) 0.0238(4) Uani 1 1 d . . . H13 H 0.9582 0.6163 0.3994 0.029 Uiso 1 1 calc R . . C14 C 0.7540(3) 0.31660(15) 0.27400(12) 0.0236(4) Uani 1 1 d . . . C15 C 0.9192(3) 0.35936(16) 0.23480(12) 0.0281(5) Uani 1 1 d . . . H15A H 0.9113 0.3553 0.1733 0.042 Uiso 1 1 calc R . . H15B H 1.0207 0.3221 0.2542 0.042 Uiso 1 1 calc R . . H15C H 0.9315 0.4282 0.2517 0.042 Uiso 1 1 calc R . . C16 C 0.7321(3) 0.20968(16) 0.24553(13) 0.0327(5) Uani 1 1 d . . . H16A H 0.6268 0.1820 0.2711 0.049 Uiso 1 1 calc R . . H16B H 0.8338 0.1714 0.2632 0.049 Uiso 1 1 calc R . . H16C H 0.7217 0.2073 0.1841 0.049 Uiso 1 1 calc R . . C17 C 0.5979(3) 0.37598(17) 0.24359(13) 0.0322(5) Uani 1 1 d . . . H17A H 0.6072 0.4434 0.2645 0.048 Uiso 1 1 calc R . . H17B H 0.4903 0.3462 0.2648 0.048 Uiso 1 1 calc R . . H17C H 0.5959 0.3765 0.1819 0.048 Uiso 1 1 calc R . . C18 C 0.6931(3) 0.44555(14) 0.55707(11) 0.0204(4) Uani 1 1 d . . . H18A H 0.7795 0.4969 0.5711 0.024 Uiso 1 1 calc R . . H18B H 0.5826 0.4629 0.5856 0.024 Uiso 1 1 calc R . . C19 C 0.7573(3) 0.34769(13) 0.59199(11) 0.0217(4) Uani 1 1 d . . . H19A H 0.6867 0.2937 0.5680 0.026 Uiso 1 1 calc R . . H19B H 0.8800 0.3373 0.5749 0.026 Uiso 1 1 calc R . . C20 C 0.7451(3) 0.34532(15) 0.68354(13) 0.0255(5) Uani 1 1 d . . . N3 N 0.81449(18) 0.40750(11) 0.41247(9) 0.0173(3) Uani 1 1 d . . . N20 N 0.7304(3) 0.34477(14) 0.75527(11) 0.0375(5) Uani 1 1 d . . . O1 O 0.61223(17) 0.28407(9) 0.41037(8) 0.0227(3) Uani 1 1 d . . . O7 O 1.09855(16) 0.36384(10) 0.40455(9) 0.0253(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 C2 0.0153(9) 0.0185(9) 0.0236(9) 0.0006(8) 0.0021(8) -0.0030(8) C4 0.0142(9) 0.0213(10) 0.0244(10) -0.0003(8) 0.0036(8) 0.0024(8) C5 0.0172(9) 0.0309(11) 0.0245(10) -0.0010(9) 0.0028(8) -0.0014(9) C6 0.0220(10) 0.0259(10) 0.0318(11) 0.0035(9) 0.0048(9) 0.0073(9) C7 0.0178(9) 0.0183(9) 0.0206(9) 0.0032(8) 0.0006(8) 0.0005(8) C8 0.0144(9) 0.0231(11) 0.0237(9) -0.0015(8) 0.0028(8) -0.0017(8) C9 0.0166(10) 0.0269(10) 0.0260(10) -0.0014(8) 0.0023(8) 0.0007(8) C10 0.0178(10) 0.0381(12) 0.0238(10) -0.0051(9) 0.0018(9) -0.0042(9) C11 0.0281(11) 0.0305(11) 0.0296(11) -0.0106(9) 0.0055(10) -0.0101(9) C12 0.0357(12) 0.0226(10) 0.0319(11) -0.0018(9) 0.0038(11) -0.0063(10) C13 0.0235(10) 0.0250(11) 0.0230(10) 0.0012(8) 0.0016(9) -0.0011(9) C14 0.0215(10) 0.0281(11) 0.0213(9) -0.0016(8) -0.0002(9) -0.0013(9) C15 0.0280(10) 0.0337(11) 0.0226(10) 0.0005(9) 0.0028(9) -0.0031(10) C16 0.0355(12) 0.0364(12) 0.0261(10) -0.0090(9) 0.0019(10) -0.0066(10) C17 0.0274(11) 0.0457(13) 0.0234(10) 0.0031(10) -0.0039(9) 0.0009(11) C18 0.0197(9) 0.0195(9) 0.0219(9) -0.0035(8) 0.0038(8) -0.0005(8) C19 0.0219(9) 0.0217(9) 0.0214(9) 0.0006(8) 0.0032(8) -0.0005(8) C20 0.0231(10) 0.0239(10) 0.0295(11) -0.0005(9) -0.0018(9) -0.0030(9) N3 0.0146(7) 0.0164(8) 0.0209(8) -0.0016(6) 0.0005(7) 0.0006(6) N20 0.0444(11) 0.0420(12) 0.0261(10) -0.0010(9) -0.0016(9) -0.0047(10) O1 0.0202(6) 0.0229(7) 0.0250(7) -0.0024(6) 0.0037(6) -0.0045(6) O7 0.0167(6) 0.0246(7) 0.0344(8) -0.0055(6) -0.0002(6) 0.0026(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 C2 O1 1.424(2) . ? C2 N3 1.476(2) . ? C2 C14 1.540(3) . ? C2 H2 1.0000 . ? C4 N3 1.500(2) . ? C4 C6 1.520(3) . ? C4 C18 1.532(3) . ? C4 C5 1.539(3) . ? C5 O1 1.425(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 O7 1.226(2) . ? C7 N3 1.368(2) . ? C7 C8 1.497(3) . ? C8 C13 1.386(3) . ? C8 C9 1.396(3) . ? C9 C10 1.380(3) . ? C9 H9 0.9500 . ? C10 C11 1.385(3) . ? C10 H10 0.9500 . ? C11 C12 1.380(3) . ? C11 H11 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C17 1.524(3) . ? C14 C15 1.528(3) . ? C14 C16 1.535(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.527(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.458(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 N20 1.145(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 O1 C2 N3 104.26(14) . . ? O1 C2 C14 112.47(15) . . ? N3 C2 C14 116.65(15) . . ? O1 C2 H2 107.7 . . ? N3 C2 H2 107.7 . . ? C14 C2 H2 107.7 . . ? N3 C4 C6 114.16(15) . . ? N3 C4 C18 113.28(15) . . ? C6 C4 C18 109.06(15) . . ? N3 C4 C5 99.99(14) . . ? C6 C4 C5 109.76(16) . . ? C18 C4 C5 110.25(15) . . ? O1 C5 C4 107.30(15) . . ? O1 C5 H5A 110.3 . . ? C4 C5 H5A 110.3 . . ? O1 C5 H5B 110.3 . . ? C4 C5 H5B 110.3 . . ? H5A C5 H5B 108.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O7 C7 N3 121.39(17) . . ? O7 C7 C8 117.92(16) . . ? N3 C7 C8 120.68(16) . . ? C13 C8 C9 119.73(17) . . ? C13 C8 C7 122.46(17) . . ? C9 C8 C7 117.46(16) . . ? C10 C9 C8 120.17(18) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.98(18) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 119.74(18) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.84(19) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C8 119.50(18) . . ? C12 C13 H13 120.2 . . ? C8 C13 H13 120.2 . . ? C17 C14 C15 108.67(16) . . ? C17 C14 C16 108.94(17) . . ? C15 C14 C16 109.45(17) . . ? C17 C14 C2 112.87(16) . . ? C15 C14 C2 110.47(16) . . ? C16 C14 C2 106.37(16) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C4 114.45(15) . . ? C19 C18 H18A 108.6 . . ? C4 C18 H18A 108.6 . . ? C19 C18 H18B 108.6 . . ? C4 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C20 C19 C18 111.16(16) . . ? C20 C19 H19A 109.4 . . ? C18 C19 H19A 109.4 . . ? C20 C19 H19B 109.4 . . ? C18 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? N20 C20 C19 177.9(2) . . ? C7 N3 C2 115.85(15) . . ? C7 N3 C4 126.93(15) . . ? C2 N3 C4 110.94(14) . . ? C2 O1 C5 107.80(14) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.137 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.031 #===END