# 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 'Elliott, Mark' _publ_contact_author_email elliottmc@cardiff.ac.uk _publ_section_title ; Reaction of heterocyclic enamines with nitrile-oxide and nitrilimine precursors ; loop_ _publ_author_name M.Elliott C.Altug Y.Durust B.Kariuki M.Zaal T.Rorstad # Attachment '- ccdc731459.cif' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_mce0901 #TrackingRef '- ccdc731459.cif' _database_code_depnum_ccdc_archive 'CCDC 731459' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H12 Cl2 N6 O2' _chemical_formula_sum 'C17 H12 Cl2 N6 O2' _chemical_formula_weight 403.23 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' Cl Cl 0.1484 0.1585 '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/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 6.8900(3) _cell_length_b 13.7810(5) _cell_length_c 18.1120(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.5030(10) _cell_angle_gamma 90.00 _cell_volume 1714.45(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2860 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.57 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.406 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8226 _exptl_absorpt_correction_T_max 0.9529 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6624 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0895 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.57 _reflns_number_total 3885 _reflns_number_gt 2860 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0700P)^2^+4.3886P] 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 3885 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1173 _refine_ls_R_factor_gt 0.0848 _refine_ls_wR_factor_ref 0.2052 _refine_ls_wR_factor_gt 0.1884 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _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 C1 C 0.2389(6) 0.9066(3) 0.4226(2) 0.0236(9) Uani 1 1 d . . . C2 C 0.3083(6) 0.8483(3) 0.4811(2) 0.0272(9) Uani 1 1 d . . . H2 H 0.3375 0.7818 0.4737 0.033 Uiso 1 1 calc R . . C3 C 0.3339(6) 0.8896(3) 0.5503(2) 0.0259(9) Uani 1 1 d . . . H3 H 0.3809 0.8521 0.5919 0.031 Uiso 1 1 calc R . . C4 C 0.2891(6) 0.9882(3) 0.5581(2) 0.0195(8) Uani 1 1 d . . . C5 C 0.2212(6) 1.0391(3) 0.4953(2) 0.0238(9) Uani 1 1 d . . . H5 H 0.1915 1.1060 0.5006 0.029 Uiso 1 1 calc R . . C6 C 0.3110(6) 1.0363(3) 0.6298(2) 0.0208(8) Uani 1 1 d . . . C7 C 0.3186(6) 1.1460(3) 0.7095(2) 0.0232(8) Uani 1 1 d . . . C8 C 0.3014(6) 1.2362(3) 0.7558(2) 0.0240(9) Uani 1 1 d . . . C9 C 0.2953(7) 1.3306(3) 0.7122(2) 0.0293(10) Uani 1 1 d . . . H9A H 0.2361 1.3208 0.6611 0.035 Uiso 1 1 calc R . . H9B H 0.4273 1.3583 0.7101 0.035 Uiso 1 1 calc R . . C10 C 0.1682(7) 1.3954(3) 0.7568(3) 0.0349(11) Uani 1 1 d . . . H10A H 0.1048 1.4467 0.7251 0.042 Uiso 1 1 calc R . . H10B H 0.2461 1.4262 0.7986 0.042 Uiso 1 1 calc R . . C11 C 0.0173(7) 1.3261(3) 0.7847(2) 0.0288(10) Uani 1 1 d . . . H11A H -0.0281 1.3492 0.8321 0.035 Uiso 1 1 calc R . . H11B H -0.0962 1.3197 0.7480 0.035 Uiso 1 1 calc R . . C12 C 0.1918(6) 1.2049(3) 0.8673(2) 0.0212(8) Uani 1 1 d . . . C13 C 0.0607(6) 1.1733(3) 0.9224(2) 0.0226(8) Uani 1 1 d . . . C14 C -0.1239(6) 1.1369(3) 0.9023(2) 0.0276(9) Uani 1 1 d . . . H14 H -0.1731 1.1372 0.8518 0.033 Uiso 1 1 calc R . . C15 C -0.2353(6) 1.1003(3) 0.9557(2) 0.0288(10) Uani 1 1 d . . . H15 H -0.3614 1.0744 0.9434 0.035 Uiso 1 1 calc R . . C16 C -0.1562(6) 1.1030(3) 1.0275(2) 0.0256(9) Uani 1 1 d . . . C17 C 0.1231(6) 1.1725(3) 0.9974(2) 0.0273(9) Uani 1 1 d . . . H17 H 0.2483 1.1982 1.0118 0.033 Uiso 1 1 calc R . . Cl1 Cl 0.20324(17) 0.85582(8) 0.33467(6) 0.0333(3) Uani 1 1 d . . . Cl2 Cl -0.29117(19) 1.05887(9) 1.09796(7) 0.0407(3) Uani 1 1 d . . . N1 N 0.1950(5) 0.9995(3) 0.42756(19) 0.0261(8) Uani 1 1 d . . . N2 N 0.2874(5) 1.1359(2) 0.63859(18) 0.0227(7) Uani 1 1 d . . . N3 N 0.3532(6) 0.9891(3) 0.69154(19) 0.0299(9) Uani 1 1 d . . . N4 N 0.1236(5) 1.2313(2) 0.79492(18) 0.0228(7) Uani 1 1 d . . . N5 N 0.3786(5) 1.2026(3) 0.88025(19) 0.0254(8) Uani 1 1 d . . . N6 N 0.0175(6) 1.1378(3) 1.0501(2) 0.0318(9) Uani 1 1 d . . . O1 O 0.3599(5) 1.0630(2) 0.74591(15) 0.0296(7) Uani 1 1 d . . . O2 O 0.4589(4) 1.2348(2) 0.81393(16) 0.0267(7) 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 0.021(2) 0.029(2) 0.021(2) -0.0079(17) 0.0045(16) -0.0077(16) C2 0.029(2) 0.022(2) 0.031(2) -0.0031(18) 0.0039(18) -0.0040(17) C3 0.031(2) 0.022(2) 0.025(2) 0.0020(17) 0.0006(18) -0.0006(17) C4 0.018(2) 0.0208(19) 0.0194(19) 0.0002(15) 0.0028(15) -0.0025(15) C5 0.028(2) 0.022(2) 0.022(2) 0.0003(17) 0.0027(17) -0.0003(16) C6 0.022(2) 0.0216(19) 0.0196(19) 0.0031(16) 0.0048(16) -0.0010(15) C7 0.020(2) 0.027(2) 0.023(2) 0.0007(17) 0.0018(16) -0.0011(16) C8 0.029(2) 0.027(2) 0.0150(19) -0.0012(17) 0.0011(16) -0.0008(17) C9 0.042(3) 0.025(2) 0.020(2) 0.0002(17) 0.0015(18) -0.0024(19) C10 0.052(3) 0.024(2) 0.028(2) -0.0040(19) -0.001(2) 0.000(2) C11 0.034(2) 0.026(2) 0.026(2) -0.0020(18) -0.0054(18) 0.0070(18) C12 0.029(2) 0.0204(19) 0.0131(18) -0.0014(15) -0.0012(16) 0.0014(16) C13 0.026(2) 0.023(2) 0.019(2) -0.0020(16) 0.0026(16) 0.0020(16) C14 0.028(2) 0.029(2) 0.024(2) -0.0016(18) -0.0055(17) 0.0034(18) C15 0.024(2) 0.029(2) 0.033(2) -0.0023(19) 0.0015(18) 0.0013(17) C16 0.029(2) 0.021(2) 0.027(2) -0.0011(17) 0.0084(18) 0.0018(16) C17 0.027(2) 0.033(2) 0.022(2) -0.0010(18) 0.0004(17) -0.0046(18) Cl1 0.0363(6) 0.0388(6) 0.0247(5) -0.0105(5) 0.0018(4) -0.0073(5) Cl2 0.0466(7) 0.0393(7) 0.0386(7) 0.0036(5) 0.0189(5) -0.0045(5) N1 0.033(2) 0.0271(18) 0.0187(17) -0.0006(15) 0.0018(15) -0.0014(15) N2 0.0285(18) 0.0216(17) 0.0178(16) -0.0013(14) 0.0005(14) -0.0010(14) N3 0.046(2) 0.0256(19) 0.0180(18) -0.0037(15) 0.0043(16) 0.0036(16) N4 0.0318(19) 0.0206(16) 0.0152(16) -0.0032(13) -0.0022(14) 0.0030(14) N5 0.029(2) 0.0290(19) 0.0181(17) 0.0022(15) 0.0020(14) -0.0035(15) N6 0.037(2) 0.037(2) 0.0223(19) -0.0022(16) 0.0044(16) -0.0047(17) O1 0.0480(19) 0.0245(15) 0.0159(14) 0.0005(12) 0.0008(13) 0.0036(13) O2 0.0238(15) 0.0355(16) 0.0203(14) 0.0008(13) -0.0001(12) -0.0060(13) _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 N1 1.320(6) . ? C1 C2 1.384(6) . ? C1 Cl1 1.740(4) . ? C2 C3 1.374(6) . ? C3 C4 1.404(6) . ? C4 C5 1.386(6) . ? C4 C6 1.455(5) . ? C5 N1 1.343(5) . ? C6 N3 1.307(5) . ? C6 N2 1.392(5) . ? C7 N2 1.294(5) . ? C7 O1 1.339(5) . ? C7 C8 1.510(6) . ? C8 O2 1.452(5) . ? C8 N4 1.464(5) . ? C8 C9 1.520(6) . ? C9 C10 1.525(6) . ? C10 C11 1.526(7) . ? C11 N4 1.502(5) . ? C12 N5 1.290(5) . ? C12 N4 1.405(5) . ? C12 C13 1.465(5) . ? C13 C14 1.389(6) . ? C13 C17 1.391(6) . ? C14 C15 1.378(6) . ? C15 C16 1.370(6) . ? C16 N6 1.324(6) . ? C16 Cl2 1.746(4) . ? C17 N6 1.335(5) . ? N3 O1 1.415(4) . ? N5 O2 1.432(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 N1 C1 C2 125.3(4) . . ? N1 C1 Cl1 115.8(3) . . ? C2 C1 Cl1 118.9(3) . . ? C3 C2 C1 118.0(4) . . ? C2 C3 C4 118.6(4) . . ? C5 C4 C3 118.1(4) . . ? C5 C4 C6 120.4(4) . . ? C3 C4 C6 121.6(4) . . ? N1 C5 C4 123.8(4) . . ? N3 C6 N2 114.4(4) . . ? N3 C6 C4 122.5(4) . . ? N2 C6 C4 123.2(3) . . ? N2 C7 O1 114.1(4) . . ? N2 C7 C8 128.8(4) . . ? O1 C7 C8 117.0(3) . . ? O2 C8 N4 104.8(3) . . ? O2 C8 C7 107.7(3) . . ? N4 C8 C7 109.6(3) . . ? O2 C8 C9 112.2(3) . . ? N4 C8 C9 107.5(3) . . ? C7 C8 C9 114.6(3) . . ? C8 C9 C10 102.7(3) . . ? C9 C10 C11 104.1(4) . . ? N4 C11 C10 104.3(4) . . ? N5 C12 N4 115.6(4) . . ? N5 C12 C13 121.9(4) . . ? N4 C12 C13 122.3(4) . . ? C14 C13 C17 117.4(4) . . ? C14 C13 C12 122.0(4) . . ? C17 C13 C12 120.5(4) . . ? C15 C14 C13 119.8(4) . . ? C16 C15 C14 117.1(4) . . ? N6 C16 C15 125.9(4) . . ? N6 C16 Cl2 114.9(3) . . ? C15 C16 Cl2 119.3(3) . . ? N6 C17 C13 123.9(4) . . ? C1 N1 C5 116.2(4) . . ? C7 N2 C6 102.0(3) . . ? C6 N3 O1 103.3(3) . . ? C12 N4 C8 103.4(3) . . ? C12 N4 C11 117.7(3) . . ? C8 N4 C11 108.6(3) . . ? C12 N5 O2 106.6(3) . . ? C16 N6 C17 116.0(4) . . ? C7 O1 N3 106.2(3) . . ? N5 O2 C8 107.3(3) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.689 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.105 # Attachment '- ccdc776572.cif' data_mce1001 _database_code_depnum_ccdc_archive 'CCDC 776572' #TrackingRef '- ccdc776572.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 N3 O2' _chemical_formula_sum 'C20 H21 N3 O2' _chemical_formula_weight 335.40 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4390(7) _cell_length_b 8.2177(7) _cell_length_c 20.2299(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.142(4) _cell_angle_gamma 90.00 _cell_volume 1696.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1620 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 22.72 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9704 _exptl_absorpt_correction_T_max 0.9965 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3780 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0744 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 22.72 _reflns_number_total 2266 _reflns_number_gt 1620 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0568P)^2^+0.5915P] 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 2266 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0921 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1395 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 0.4636(3) 0.4437(4) 0.13006(16) 0.0278(8) Uani 1 1 d . . . C2 C 0.5254(3) 0.3827(4) 0.19912(15) 0.0308(8) Uani 1 1 d . . . H2A H 0.4813 0.4297 0.2335 0.037 Uiso 1 1 calc R . . H2B H 0.6195 0.4119 0.2108 0.037 Uiso 1 1 calc R . . C3 C 0.5082(3) 0.1983(4) 0.19560(17) 0.0394(9) Uani 1 1 d . . . H3A H 0.4856 0.1560 0.2375 0.047 Uiso 1 1 calc R . . H3B H 0.5894 0.1443 0.1890 0.047 Uiso 1 1 calc R . . C4 C 0.3959(3) 0.1697(4) 0.13478(17) 0.0386(9) Uani 1 1 d . . . H4A H 0.4132 0.0741 0.1082 0.046 Uiso 1 1 calc R . . H4B H 0.3117 0.1538 0.1491 0.046 Uiso 1 1 calc R . . C5 C 0.4772(3) 0.6001(4) 0.10786(15) 0.0261(8) Uani 1 1 d . . . C6 C 0.4075(3) 0.6490(4) 0.04190(16) 0.0302(8) Uani 1 1 d . . . C7 C 0.3489(3) 0.8671(4) -0.03549(16) 0.0391(9) Uani 1 1 d . . . H7A H 0.3669 0.7984 -0.0721 0.059 Uiso 1 1 calc R . . H7B H 0.3742 0.9796 -0.0425 0.059 Uiso 1 1 calc R . . H7C H 0.2551 0.8630 -0.0353 0.059 Uiso 1 1 calc R . . C8 C 0.5573(3) 0.7169(4) 0.15550(15) 0.0273(8) Uani 1 1 d . . . C9 C 0.5091(3) 0.7762(4) 0.21476(16) 0.0272(8) Uani 1 1 d . . . C10 C 0.5950(3) 0.8158(4) 0.27543(15) 0.0318(8) Uani 1 1 d . . . H10 H 0.6864 0.7999 0.2794 0.038 Uiso 1 1 calc R . . C11 C 0.5497(4) 0.8777(4) 0.32979(17) 0.0378(9) Uani 1 1 d . . . H11 H 0.6100 0.9035 0.3705 0.045 Uiso 1 1 calc R . . C12 C 0.4170(4) 0.9021(4) 0.32523(17) 0.0422(10) Uani 1 1 d . . . H12 H 0.3859 0.9474 0.3621 0.051 Uiso 1 1 calc R . . C13 C 0.3305(3) 0.8598(4) 0.26628(17) 0.0403(9) Uani 1 1 d . . . H13 H 0.2392 0.8758 0.2629 0.048 Uiso 1 1 calc R . . C14 C 0.3746(3) 0.7942(4) 0.21194(17) 0.0342(8) Uani 1 1 d . . . H14 H 0.3132 0.7613 0.1726 0.041 Uiso 1 1 calc R . . C15 C 0.8450(3) 0.7702(4) 0.09032(15) 0.0257(8) Uani 1 1 d . . . C16 C 0.9072(3) 0.6944(4) 0.04419(15) 0.0301(8) Uani 1 1 d . . . H16 H 0.8671 0.6036 0.0190 0.036 Uiso 1 1 calc R . . C17 C 1.0271(3) 0.7502(4) 0.03468(17) 0.0371(9) Uani 1 1 d . . . H17 H 1.0684 0.6977 0.0029 0.044 Uiso 1 1 calc R . . C18 C 1.0871(3) 0.8814(4) 0.07105(16) 0.0375(9) Uani 1 1 d . . . H18 H 1.1698 0.9190 0.0648 0.045 Uiso 1 1 calc R . . C19 C 1.0254(3) 0.9573(4) 0.11660(16) 0.0349(9) Uani 1 1 d . . . H19 H 1.0667 1.0471 0.1420 0.042 Uiso 1 1 calc R . . C20 C 0.9044(3) 0.9049(4) 0.12592(16) 0.0320(8) Uani 1 1 d . . . H20 H 0.8621 0.9605 0.1565 0.038 Uiso 1 1 calc R . . O1 O 0.3378(2) 0.5603(3) -0.00014(11) 0.0348(6) Uani 1 1 d . . . O2 O 0.4233(2) 0.8084(3) 0.02880(10) 0.0341(6) Uani 1 1 d . . . N1 N 0.3952(3) 0.3213(3) 0.09590(14) 0.0359(7) Uani 1 1 d . . . H1 H 0.3532 0.3307 0.0536 0.043 Uiso 1 1 calc R . . N2 N 0.6716(2) 0.7718(3) 0.15018(12) 0.0279(7) Uani 1 1 d . . . N3 N 0.7230(2) 0.7142(3) 0.09816(12) 0.0311(7) Uani 1 1 d . . . H3 H 0.6796 0.6423 0.0698 0.037 Uiso 1 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 C1 0.0258(17) 0.0257(19) 0.0330(18) -0.0017(16) 0.0081(14) -0.0008(16) C2 0.0306(18) 0.032(2) 0.0303(18) 0.0045(16) 0.0065(15) 0.0012(15) C3 0.045(2) 0.030(2) 0.043(2) 0.0059(18) 0.0097(18) -0.0039(18) C4 0.046(2) 0.026(2) 0.046(2) 0.0007(17) 0.0149(17) -0.0054(18) C5 0.0266(18) 0.0258(19) 0.0251(17) 0.0001(15) 0.0037(14) -0.0012(15) C6 0.0312(18) 0.026(2) 0.0343(19) -0.0008(17) 0.0090(16) -0.0028(17) C7 0.042(2) 0.039(2) 0.0341(19) 0.0113(17) 0.0019(16) 0.0037(18) C8 0.0264(18) 0.0248(18) 0.0281(18) 0.0003(15) 0.0001(14) 0.0005(16) C9 0.0294(18) 0.0224(18) 0.0302(18) 0.0009(15) 0.0076(15) -0.0015(15) C10 0.0327(19) 0.0294(19) 0.0334(19) -0.0027(16) 0.0067(16) -0.0043(16) C11 0.049(2) 0.031(2) 0.033(2) -0.0019(17) 0.0073(17) -0.0046(18) C12 0.058(3) 0.036(2) 0.038(2) -0.0008(18) 0.0228(19) -0.0018(19) C13 0.035(2) 0.042(2) 0.048(2) 0.0049(19) 0.0180(18) 0.0031(18) C14 0.0316(19) 0.035(2) 0.0363(19) 0.0031(17) 0.0082(15) -0.0007(17) C15 0.0240(17) 0.0274(19) 0.0245(17) 0.0041(15) 0.0023(14) 0.0016(15) C16 0.0344(19) 0.0277(19) 0.0282(18) -0.0035(15) 0.0067(15) -0.0043(16) C17 0.033(2) 0.043(2) 0.037(2) -0.0018(17) 0.0118(16) -0.0004(17) C18 0.0302(19) 0.044(2) 0.039(2) 0.0012(18) 0.0095(16) -0.0064(17) C19 0.0322(19) 0.035(2) 0.0355(19) -0.0015(17) 0.0026(16) -0.0077(17) C20 0.0333(19) 0.034(2) 0.0278(17) -0.0012(16) 0.0048(15) -0.0013(17) O1 0.0358(14) 0.0344(14) 0.0321(12) -0.0065(11) 0.0024(10) -0.0071(12) O2 0.0391(13) 0.0289(14) 0.0308(13) 0.0048(11) -0.0006(10) -0.0029(11) N1 0.0409(17) 0.0278(17) 0.0369(16) 0.0003(14) 0.0035(13) -0.0041(15) N2 0.0269(15) 0.0295(16) 0.0267(14) -0.0043(12) 0.0044(12) -0.0031(13) N3 0.0286(15) 0.0350(17) 0.0298(15) -0.0097(13) 0.0065(12) -0.0067(13) _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 N1 1.338(4) . ? C1 C5 1.379(4) . ? C1 C2 1.497(4) . ? C2 C3 1.526(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.528(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.473(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.436(4) . ? C5 C8 1.486(4) . ? C6 O1 1.234(4) . ? C6 O2 1.353(4) . ? C7 O2 1.450(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N2 1.301(4) . ? C8 C9 1.477(4) . ? C9 C10 1.397(4) . ? C9 C14 1.401(4) . ? C10 C11 1.382(5) . ? C10 H10 0.9500 . ? C11 C12 1.383(5) . ? C11 H11 0.9500 . ? C12 C13 1.380(5) . ? C12 H12 0.9500 . ? C13 C14 1.387(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.391(4) . ? C15 C20 1.393(4) . ? C15 N3 1.395(4) . ? C16 C17 1.383(4) . ? C16 H16 0.9500 . ? C17 C18 1.379(5) . ? C17 H17 0.9500 . ? C18 C19 1.380(5) . ? C18 H18 0.9500 . ? C19 C20 1.384(4) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? N1 H1 0.8800 . ? N2 N3 1.363(3) . ? N3 H3 0.8800 . ? 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 N1 C1 C5 127.8(3) . . ? N1 C1 C2 108.0(3) . . ? C5 C1 C2 124.2(3) . . ? C1 C2 C3 105.4(3) . . ? C1 C2 H2A 110.7 . . ? C3 C2 H2A 110.7 . . ? C1 C2 H2B 110.7 . . ? C3 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? C2 C3 C4 104.6(3) . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3B 110.8 . . ? C4 C3 H3B 110.8 . . ? H3A C3 H3B 108.9 . . ? N1 C4 C3 102.5(3) . . ? N1 C4 H4A 111.3 . . ? C3 C4 H4A 111.3 . . ? N1 C4 H4B 111.3 . . ? C3 C4 H4B 111.3 . . ? H4A C4 H4B 109.2 . . ? C1 C5 C6 119.8(3) . . ? C1 C5 C8 118.2(3) . . ? C6 C5 C8 121.9(3) . . ? O1 C6 O2 121.0(3) . . ? O1 C6 C5 125.8(3) . . ? O2 C6 C5 113.2(3) . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C9 115.3(3) . . ? N2 C8 C5 124.8(3) . . ? C9 C8 C5 119.9(3) . . ? C10 C9 C14 117.6(3) . . ? C10 C9 C8 121.7(3) . . ? C14 C9 C8 120.7(3) . . ? C11 C10 C9 121.4(3) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 120.4(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 119.0(3) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 121.1(3) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C13 C14 C9 120.4(3) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? C16 C15 C20 118.9(3) . . ? C16 C15 N3 119.7(3) . . ? C20 C15 N3 121.4(3) . . ? C17 C16 C15 120.5(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 120.5(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 119.1(3) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C18 C19 C20 121.2(3) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C19 C20 C15 119.8(3) . . ? C19 C20 H20 120.1 . . ? C15 C20 H20 120.1 . . ? C6 O2 C7 115.7(3) . . ? C1 N1 C4 114.7(3) . . ? C1 N1 H1 122.7 . . ? C4 N1 H1 122.7 . . ? C8 N2 N3 117.4(3) . . ? N2 N3 C15 119.4(3) . . ? N2 N3 H3 120.3 . . ? C15 N3 H3 120.3 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 22.72 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.272 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.054