data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Prof Andrew Holmes' _publ_contact_author_address ; Chemistry University of Cambridge Lensfield Road Cambridge CAMBS CB2 1EW UNITED KINGDOM ; _publ_contact_author_email ABH1@CAM.AC.UK _publ_section_title ; Investigation of conjugate addition / intramolecular nitrone dipolar cycloadditions and their use in the synthesis of dendrobatid alkaloid precursors ; ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; loop_ _publ_author_name 'Andrew Holmes' 'Ian Collins' 'John E. Davies' 'Jonathan M. Goodman' 'Helen Horsley' 'Sofia I. Pascu' ; M.A.Silva ; data_ah0304 _database_code_depnum_ccdc_archive 'CCDC 230717' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H17 N3 O' _chemical_formula_sum 'C13 H17 N3 O' _chemical_formula_weight 231.30 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 15.5820(9) _cell_length_b 9.9509(6) _cell_length_c 7.9189(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.128(3) _cell_angle_gamma 90.00 _cell_volume 1218.37(13) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5714 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.896 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 3327 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.45 _diffrn_reflns_theta_max 24.96 _reflns_number_total 1725 _reflns_number_gt 1648 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0219P)^2^+0.4026P] 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 -1.0(15) _refine_ls_number_reflns 1725 _refine_ls_number_parameters 154 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.097 _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 O1 O 0.90248(8) 0.07278(13) 0.94283(17) 0.0331(3) Uani 1 1 d . . . N1 N 0.86782(9) 0.20849(15) 0.97281(18) 0.0259(4) Uani 1 1 d . . . N2 N 0.75815(13) 0.2104(2) 1.3599(2) 0.0488(5) Uani 1 1 d . . . N3 N 1.02205(13) 0.2993(2) 0.4945(2) 0.0488(5) Uani 1 1 d . . . C1 C 0.73834(13) 0.1034(2) 1.0563(2) 0.0323(5) Uani 1 1 d . . . H1A H 0.6760 0.0871 1.0215 0.039 Uiso 1 1 calc R . . H1B H 0.7683 0.0154 1.0605 0.039 Uiso 1 1 calc R . . C2 C 0.77362(11) 0.19252(18) 0.9232(2) 0.0259(4) Uani 1 1 d . . . H2 H 0.7641 0.1459 0.8106 0.031 Uiso 1 1 calc R . . C3 C 0.72976(12) 0.3291(2) 0.9056(2) 0.0305(4) Uani 1 1 d . . . H3A H 0.6668 0.3171 0.8732 0.037 Uiso 1 1 calc R . . H3B H 0.7385 0.3767 1.0162 0.037 Uiso 1 1 calc R . . C4 C 0.76685(12) 0.4124(2) 0.7715(2) 0.0317(4) Uani 1 1 d . . . H4A H 0.7383 0.5014 0.7610 0.038 Uiso 1 1 calc R . . H4B H 0.7565 0.3667 0.6597 0.038 Uiso 1 1 calc R . . C5 C 0.86347(12) 0.42974(19) 0.8234(2) 0.0295(4) Uani 1 1 d . . . H5A H 0.8723 0.4884 0.9251 0.035 Uiso 1 1 calc R . . H5B H 0.8885 0.4762 0.7304 0.035 Uiso 1 1 calc R . . C6 C 0.91284(11) 0.29847(18) 0.8636(2) 0.0261(4) Uani 1 1 d . . . C7 C 0.92244(12) 0.20625(19) 0.7092(2) 0.0289(4) Uani 1 1 d . . . H7 H 0.8639 0.1874 0.6468 0.035 Uiso 1 1 calc R . . C8 C 0.95628(13) 0.0795(2) 0.8067(3) 0.0339(5) Uani 1 1 d . . . H8 H 0.9486 -0.0020 0.7325 0.041 Uiso 1 1 calc R . . C9 C 1.05008(13) 0.0956(2) 0.8841(3) 0.0414(5) Uani 1 1 d . . . H9A H 1.0864 0.1175 0.7937 0.050 Uiso 1 1 calc R . . H9B H 1.0713 0.0103 0.9384 0.050 Uiso 1 1 calc R . . C10 C 1.05700(13) 0.2076(2) 1.0162(3) 0.0406(5) Uani 1 1 d . . . H10A H 1.1184 0.2340 1.0433 0.049 Uiso 1 1 calc R . . H10B H 1.0369 0.1735 1.1220 0.049 Uiso 1 1 calc R . . C11 C 1.00373(12) 0.3313(2) 0.9551(2) 0.0346(5) Uani 1 1 d . . . H11A H 1.0358 0.3831 0.8765 0.042 Uiso 1 1 calc R . . H11B H 0.9975 0.3893 1.0543 0.042 Uiso 1 1 calc R . . C12 C 0.74999(13) 0.1639(2) 1.2265(3) 0.0345(5) Uani 1 1 d . . . C13 C 0.97891(13) 0.2577(2) 0.5893(3) 0.0357(5) 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 O1 0.0317(7) 0.0292(7) 0.0400(7) 0.0039(6) 0.0105(6) 0.0080(6) N1 0.0237(8) 0.0275(8) 0.0270(8) 0.0005(6) 0.0045(7) 0.0048(6) N2 0.0585(13) 0.0558(12) 0.0338(11) 0.0027(9) 0.0128(10) 0.0097(10) N3 0.0395(11) 0.0624(13) 0.0476(11) 0.0065(9) 0.0176(10) 0.0046(9) C1 0.0288(10) 0.0347(11) 0.0342(10) 0.0027(9) 0.0070(8) 0.0003(8) C2 0.0229(10) 0.0321(10) 0.0226(8) -0.0031(8) 0.0022(7) -0.0004(8) C3 0.0246(10) 0.0373(11) 0.0295(9) 0.0006(8) 0.0030(8) 0.0051(8) C4 0.0292(10) 0.0351(11) 0.0309(10) 0.0022(9) 0.0041(8) 0.0057(8) C5 0.0306(10) 0.0304(10) 0.0275(9) 0.0013(8) 0.0042(9) -0.0001(8) C6 0.0231(10) 0.0314(10) 0.0237(10) -0.0015(8) 0.0023(8) -0.0004(8) C7 0.0246(10) 0.0357(10) 0.0268(10) -0.0013(8) 0.0047(8) 0.0016(8) C8 0.0301(10) 0.0388(11) 0.0345(10) -0.0015(9) 0.0103(8) 0.0070(9) C9 0.0279(11) 0.0504(13) 0.0469(11) 0.0092(11) 0.0085(10) 0.0121(10) C10 0.0236(10) 0.0571(14) 0.0394(11) 0.0070(10) -0.0030(9) 0.0013(9) C11 0.0244(10) 0.0441(12) 0.0346(10) -0.0019(9) 0.0008(9) -0.0049(9) C12 0.0326(11) 0.0390(11) 0.0335(11) 0.0100(9) 0.0110(9) 0.0068(9) C13 0.0289(10) 0.0443(12) 0.0346(10) -0.0018(9) 0.0063(9) 0.0076(9) _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 O1 C8 1.447(2) . ? O1 N1 1.4844(19) . ? N1 C2 1.480(2) . ? N1 C6 1.481(2) . ? N2 C12 1.145(3) . ? N3 C13 1.145(3) . ? C1 C12 1.467(3) . ? C1 C2 1.531(3) . ? C2 C3 1.520(3) . ? C3 C4 1.517(3) . ? C4 C5 1.520(3) . ? C5 C6 1.529(3) . ? C6 C11 1.544(3) . ? C6 C7 1.550(2) . ? C7 C13 1.465(3) . ? C7 C8 1.537(3) . ? C8 C9 1.522(3) . ? C9 C10 1.523(3) . ? C10 C11 1.530(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 C8 O1 N1 109.45(13) . . ? C2 N1 C6 115.85(13) . . ? C2 N1 O1 103.20(12) . . ? C6 N1 O1 104.39(12) . . ? C12 C1 C2 112.37(16) . . ? N1 C2 C3 110.37(14) . . ? N1 C2 C1 107.98(14) . . ? C3 C2 C1 112.68(15) . . ? C4 C3 C2 110.28(15) . . ? C3 C4 C5 108.83(15) . . ? C4 C5 C6 114.53(15) . . ? N1 C6 C5 112.05(14) . . ? N1 C6 C11 109.12(14) . . ? C5 C6 C11 109.00(15) . . ? N1 C6 C7 101.63(13) . . ? C5 C6 C7 115.90(14) . . ? C11 C6 C7 108.82(15) . . ? C13 C7 C8 114.58(16) . . ? C13 C7 C6 115.38(16) . . ? C8 C7 C6 98.66(14) . . ? O1 C8 C9 108.72(16) . . ? O1 C8 C7 102.57(14) . . ? C9 C8 C7 111.62(17) . . ? C8 C9 C10 109.65(17) . . ? C9 C10 C11 112.47(16) . . ? C10 C11 C6 114.11(17) . . ? N2 C12 C1 179.2(2) . . ? N3 C13 C7 178.9(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.111 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.030 data_ah0305 _database_code_depnum_ccdc_archive 'CCDC 230718' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H17 N3 O' _chemical_formula_sum 'C13 H17 N3 O' _chemical_formula_weight 231.30 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.84160(10) _cell_length_b 6.9482(2) _cell_length_c 31.7123(12) _cell_angle_alpha 86.9810(10) _cell_angle_beta 89.7330(10) _cell_angle_gamma 68.6350(10) _cell_volume 1196.89(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 14549 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.879 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7169 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0656 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 25.04 _reflns_number_total 4054 _reflns_number_gt 3114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0000P)^2^+1.2698P] 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 4054 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1306 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _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 O1_1 O -1.3146(3) 0.8322(3) 0.36056(6) 0.0301(5) Uani 1 1 d . . . N1_1 N -1.3602(4) 0.6485(3) 0.37801(7) 0.0248(5) Uani 1 1 d . . . N2_1 N -1.6891(5) 0.8311(4) 0.51482(8) 0.0435(7) Uani 1 1 d . . . N3_1 N -1.7444(5) 0.8932(4) 0.28544(9) 0.0491(7) Uani 1 1 d . . . C1_1 C -1.5853(5) 0.8544(4) 0.43500(8) 0.0309(7) Uani 1 1 d . . . H1A_1 H -1.5383 0.9761 0.4288 0.037 Uiso 1 1 calc R . . H1B_1 H -1.7309 0.8708 0.4173 0.037 Uiso 1 1 calc R . . C2_1 C -1.3727(5) 0.6574(4) 0.42409(8) 0.0258(6) Uani 1 1 d . . . H2_1 H -1.4179 0.5383 0.4349 0.031 Uiso 1 1 calc R . . C3_1 C -1.1316(5) 0.6328(5) 0.44596(9) 0.0344(7) Uani 1 1 d . . . H3A_1 H -1.1521 0.6306 0.4770 0.041 Uiso 1 1 calc R . . H3B_1 H -1.0823 0.7511 0.4374 0.041 Uiso 1 1 calc R . . C4_1 C -0.9329(5) 0.4304(5) 0.43360(9) 0.0378(7) Uani 1 1 d . . . H4A_1 H -0.7748 0.4125 0.4476 0.045 Uiso 1 1 calc R . . H4B_1 H -0.9800 0.3117 0.4428 0.045 Uiso 1 1 calc R . . C5_1 C -0.9049(5) 0.4377(5) 0.38593(8) 0.0316(7) Uani 1 1 d . . . H5A_1 H -0.7802 0.3051 0.3778 0.038 Uiso 1 1 calc R . . H5B_1 H -0.8439 0.5494 0.3775 0.038 Uiso 1 1 calc R . . C6_1 C -1.1456(5) 0.4751(4) 0.36187(8) 0.0261(6) Uani 1 1 d . . . C7_1 C -1.2235(5) 0.2887(4) 0.35882(9) 0.0294(6) Uani 1 1 d . . . H7A_1 H -1.0785 0.1594 0.3568 0.035 Uiso 1 1 calc R . . H7B_1 H -1.3208 0.2743 0.3836 0.035 Uiso 1 1 calc R . . C8_1 C -1.3798(5) 0.3385(4) 0.31833(9) 0.0320(7) Uani 1 1 d . . . H8A_1 H -1.5459 0.4418 0.3229 0.038 Uiso 1 1 calc R . . H8B_1 H -1.3955 0.2123 0.3078 0.038 Uiso 1 1 calc R . . C9_1 C -1.2337(5) 0.4264(4) 0.28777(9) 0.0317(7) Uani 1 1 d . . . H9A_1 H -1.0955 0.3139 0.2756 0.038 Uiso 1 1 calc R . . H9B_1 H -1.3406 0.5131 0.2645 0.038 Uiso 1 1 calc R . . C10_1 C -1.1392(5) 0.5565(4) 0.31550(8) 0.0270(6) Uani 1 1 d . . . H10_1 H -0.9667 0.5385 0.3078 0.032 Uiso 1 1 calc R . . C11_1 C -1.2971(5) 0.7897(4) 0.31690(8) 0.0286(6) Uani 1 1 d . . . H11_1 H -1.2113 0.8731 0.3017 0.034 Uiso 1 1 calc R . . C12_1 C -1.6479(5) 0.8455(5) 0.47979(10) 0.0320(7) Uani 1 1 d . . . C13_1 C -1.5492(6) 0.8471(4) 0.29902(9) 0.0326(7) Uani 1 1 d . . . O1_2 O -0.7931(3) 0.7882(3) 0.13649(6) 0.0301(5) Uani 1 1 d . . . N1_2 N -0.8432(4) 0.6079(3) 0.12262(7) 0.0241(5) Uani 1 1 d . . . N2_2 N -1.1917(5) 0.8326(4) -0.01616(8) 0.0444(7) Uani 1 1 d . . . N3_2 N -1.2097(5) 0.8352(4) 0.21286(8) 0.0446(7) Uani 1 1 d . . . C1_2 C -1.0783(5) 0.8271(4) 0.06368(9) 0.0312(7) Uani 1 1 d . . . H1A_2 H -1.2224 0.8382 0.0813 0.037 Uiso 1 1 calc R . . H1B_2 H -1.0305 0.9469 0.0687 0.037 Uiso 1 1 calc R . . C2_2 C -0.8642(5) 0.6257(4) 0.07657(8) 0.0263(6) Uani 1 1 d . . . H2_2 H -0.9134 0.5096 0.0680 0.032 Uiso 1 1 calc R . . C3_2 C -0.6274(5) 0.6044(5) 0.05330(9) 0.0339(7) Uani 1 1 d . . . H3A_2 H -0.6552 0.6080 0.0224 0.041 Uiso 1 1 calc R . . H3B_2 H -0.5752 0.7206 0.0595 0.041 Uiso 1 1 calc R . . C4_2 C -0.4283(5) 0.3991(5) 0.06794(9) 0.0365(7) Uani 1 1 d . . . H4A_2 H -0.4785 0.2828 0.0610 0.044 Uiso 1 1 calc R . . H4B_2 H -0.2728 0.3829 0.0533 0.044 Uiso 1 1 calc R . . C5_2 C -0.3899(5) 0.3962(5) 0.11553(8) 0.0305(7) Uani 1 1 d . . . H5A_2 H -0.3242 0.5045 0.1218 0.037 Uiso 1 1 calc R . . H5B_2 H -0.2657 0.2607 0.1252 0.037 Uiso 1 1 calc R . . C6_2 C -0.6271(5) 0.4327(4) 0.14053(8) 0.0252(6) Uani 1 1 d . . . C7_2 C -0.7042(5) 0.2445(4) 0.14742(9) 0.0297(6) Uani 1 1 d . . . H7A_2 H -0.5585 0.1145 0.1504 0.036 Uiso 1 1 calc R . . H7B_2 H -0.8086 0.2355 0.1237 0.036 Uiso 1 1 calc R . . C8_2 C -0.8494(5) 0.2857(5) 0.18868(9) 0.0335(7) Uani 1 1 d . . . H8A_2 H -1.0175 0.3892 0.1838 0.040 Uiso 1 1 calc R . . H8B_2 H -0.8602 0.1568 0.2018 0.040 Uiso 1 1 calc R . . C9_2 C -0.6954(5) 0.3694(5) 0.21615(9) 0.0325(7) Uani 1 1 d . . . H9A_2 H -0.5536 0.2549 0.2293 0.039 Uiso 1 1 calc R . . H9B_2 H -0.7959 0.4520 0.2387 0.039 Uiso 1 1 calc R . . C10_2 C -0.6090(5) 0.5051(4) 0.18524(8) 0.0276(6) Uani 1 1 d . . . H10_2 H -0.4347 0.4864 0.1919 0.033 Uiso 1 1 calc R . . C11_2 C -0.7676(5) 0.7372(4) 0.18084(8) 0.0291(6) Uani 1 1 d . . . H11_2 H -0.6798 0.8183 0.1943 0.035 Uiso 1 1 calc R . . C12_2 C -1.1456(5) 0.8328(5) 0.01907(10) 0.0332(7) Uani 1 1 d . . . C13_2 C -1.0171(5) 0.7905(4) 0.19910(9) 0.0317(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 O1_1 0.0397(11) 0.0282(11) 0.0266(10) -0.0022(8) 0.0038(8) -0.0171(9) N1_1 0.0264(12) 0.0247(12) 0.0243(12) 0.0009(9) 0.0025(9) -0.0108(10) N2_1 0.0384(15) 0.0529(18) 0.0383(17) -0.0063(13) 0.0084(12) -0.0150(13) N3_1 0.0403(17) 0.0525(19) 0.0433(17) -0.0005(14) -0.0059(13) -0.0038(14) C1_1 0.0292(15) 0.0332(17) 0.0277(15) -0.0046(13) 0.0027(12) -0.0078(13) C2_1 0.0245(14) 0.0309(16) 0.0217(14) -0.0001(12) 0.0011(11) -0.0101(12) C3_1 0.0279(15) 0.052(2) 0.0224(15) -0.0020(13) -0.0017(11) -0.0136(14) C4_1 0.0219(15) 0.055(2) 0.0297(16) 0.0036(14) -0.0038(12) -0.0070(14) C5_1 0.0219(14) 0.0403(18) 0.0295(15) -0.0005(13) 0.0013(11) -0.0077(13) C6_1 0.0211(14) 0.0310(16) 0.0243(14) -0.0025(12) 0.0033(11) -0.0071(12) C7_1 0.0296(15) 0.0232(15) 0.0319(16) -0.0019(12) 0.0056(12) -0.0055(12) C8_1 0.0346(16) 0.0273(16) 0.0368(17) -0.0074(13) 0.0028(13) -0.0137(13) C9_1 0.0338(16) 0.0312(16) 0.0275(15) -0.0057(12) 0.0008(12) -0.0084(13) C10_1 0.0226(14) 0.0303(16) 0.0274(15) -0.0013(12) 0.0026(11) -0.0089(12) C11_1 0.0321(15) 0.0305(16) 0.0235(14) 0.0011(12) 0.0022(11) -0.0120(13) C12_1 0.0247(15) 0.0345(17) 0.0346(18) -0.0066(13) 0.0023(12) -0.0074(13) C13_1 0.0376(18) 0.0283(16) 0.0270(15) 0.0014(12) 0.0021(13) -0.0065(14) O1_2 0.0383(11) 0.0300(11) 0.0264(10) -0.0033(8) 0.0013(8) -0.0174(9) N1_2 0.0239(12) 0.0234(12) 0.0248(12) -0.0025(9) -0.0009(9) -0.0082(10) N2_2 0.0391(15) 0.0555(18) 0.0360(16) 0.0043(13) -0.0081(12) -0.0151(14) N3_2 0.0408(16) 0.0429(17) 0.0403(16) -0.0017(13) 0.0058(13) -0.0039(13) C1_2 0.0290(15) 0.0331(17) 0.0288(15) 0.0022(12) 0.0004(12) -0.0086(13) C2_2 0.0235(14) 0.0301(16) 0.0241(14) -0.0013(12) -0.0005(11) -0.0086(12) C3_2 0.0285(15) 0.0473(19) 0.0242(15) -0.0025(13) 0.0038(12) -0.0119(14) C4_2 0.0226(15) 0.052(2) 0.0297(16) -0.0064(14) 0.0031(12) -0.0071(14) C5_2 0.0203(14) 0.0373(17) 0.0309(15) -0.0038(13) 0.0014(11) -0.0068(13) C6_2 0.0194(13) 0.0302(16) 0.0244(14) -0.0030(12) 0.0000(10) -0.0067(12) C7_2 0.0299(15) 0.0218(15) 0.0360(16) -0.0028(12) -0.0022(12) -0.0075(12) C8_2 0.0355(17) 0.0291(16) 0.0363(17) 0.0009(13) 0.0035(13) -0.0127(14) C9_2 0.0323(16) 0.0349(17) 0.0272(15) 0.0013(13) 0.0008(12) -0.0091(14) C10_2 0.0215(14) 0.0335(16) 0.0273(15) -0.0018(12) -0.0019(11) -0.0095(12) C11_2 0.0322(15) 0.0316(16) 0.0261(15) -0.0042(12) 0.0027(12) -0.0143(13) C12_2 0.0244(15) 0.0322(17) 0.0401(19) 0.0041(14) -0.0003(13) -0.0078(13) C13_2 0.0346(17) 0.0290(16) 0.0270(15) -0.0037(12) 0.0009(13) -0.0057(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 O1_1 C11_1 1.426(3) . ? O1_1 N1_1 1.476(3) . ? N1_1 C2_1 1.466(3) . ? N1_1 C6_1 1.498(3) . ? N2_1 C12_1 1.142(4) . ? N3_1 C13_1 1.146(4) . ? C1_1 C12_1 1.469(4) . ? C1_1 C2_1 1.531(4) . ? C1_1 H1A_1 0.9900 . ? C1_1 H1B_1 0.9900 . ? C2_1 C3_1 1.521(4) . ? C2_1 H2_1 1.0000 . ? C3_1 C4_1 1.531(4) . ? C3_1 H3A_1 0.9900 . ? C3_1 H3B_1 0.9900 . ? C4_1 C5_1 1.520(4) . ? C4_1 H4A_1 0.9900 . ? C4_1 H4B_1 0.9900 . ? C5_1 C6_1 1.533(4) . ? C5_1 H5A_1 0.9900 . ? C5_1 H5B_1 0.9900 . ? C6_1 C7_1 1.529(4) . ? C6_1 C10_1 1.553(4) . ? C7_1 C8_1 1.528(4) . ? C7_1 H7A_1 0.9900 . ? C7_1 H7B_1 0.9900 . ? C8_1 C9_1 1.533(4) . ? C8_1 H8A_1 0.9900 . ? C8_1 H8B_1 0.9900 . ? C9_1 C10_1 1.532(4) . ? C9_1 H9A_1 0.9900 . ? C9_1 H9B_1 0.9900 . ? C10_1 C11_1 1.548(4) . ? C10_1 H10_1 1.0000 . ? C11_1 C13_1 1.485(4) . ? C11_1 H11_1 1.0000 . ? O1_2 C11_2 1.427(3) . ? O1_2 N1_2 1.475(3) . ? N1_2 C2_2 1.461(3) . ? N1_2 C6_2 1.487(3) . ? N2_2 C12_2 1.151(4) . ? N3_2 C13_2 1.144(3) . ? C1_2 C12_2 1.464(4) . ? C1_2 C2_2 1.536(4) . ? C1_2 H1A_2 0.9900 . ? C1_2 H1B_2 0.9900 . ? C2_2 C3_2 1.527(4) . ? C2_2 H2_2 1.0000 . ? C3_2 C4_2 1.526(4) . ? C3_2 H3A_2 0.9900 . ? C3_2 H3B_2 0.9900 . ? C4_2 C5_2 1.525(4) . ? C4_2 H4A_2 0.9900 . ? C4_2 H4B_2 0.9900 . ? C5_2 C6_2 1.538(3) . ? C5_2 H5A_2 0.9900 . ? C5_2 H5B_2 0.9900 . ? C6_2 C7_2 1.536(4) . ? C6_2 C10_2 1.546(4) . ? C7_2 C8_2 1.539(4) . ? C7_2 H7A_2 0.9900 . ? C7_2 H7B_2 0.9900 . ? C8_2 C9_2 1.532(4) . ? C8_2 H8A_2 0.9900 . ? C8_2 H8B_2 0.9900 . ? C9_2 C10_2 1.533(4) . ? C9_2 H9A_2 0.9900 . ? C9_2 H9B_2 0.9900 . ? C10_2 C11_2 1.538(4) . ? C10_2 H10_2 1.0000 . ? C11_2 C13_2 1.489(4) . ? C11_2 H11_2 1.0000 . ? 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 C11_1 O1_1 N1_1 99.54(18) . . ? C2_1 N1_1 O1_1 108.29(19) . . ? C2_1 N1_1 C6_1 115.3(2) . . ? O1_1 N1_1 C6_1 101.93(17) . . ? C12_1 C1_1 C2_1 110.8(2) . . ? C12_1 C1_1 H1A_1 109.5 . . ? C2_1 C1_1 H1A_1 109.5 . . ? C12_1 C1_1 H1B_1 109.5 . . ? C2_1 C1_1 H1B_1 109.5 . . ? H1A_1 C1_1 H1B_1 108.1 . . ? N1_1 C2_1 C3_1 114.8(2) . . ? N1_1 C2_1 C1_1 108.5(2) . . ? C3_1 C2_1 C1_1 113.2(2) . . ? N1_1 C2_1 H2_1 106.6 . . ? C3_1 C2_1 H2_1 106.6 . . ? C1_1 C2_1 H2_1 106.6 . . ? C2_1 C3_1 C4_1 109.1(2) . . ? C2_1 C3_1 H3A_1 109.9 . . ? C4_1 C3_1 H3A_1 109.9 . . ? C2_1 C3_1 H3B_1 109.9 . . ? C4_1 C3_1 H3B_1 109.9 . . ? H3A_1 C3_1 H3B_1 108.3 . . ? C5_1 C4_1 C3_1 108.8(2) . . ? C5_1 C4_1 H4A_1 109.9 . . ? C3_1 C4_1 H4A_1 109.9 . . ? C5_1 C4_1 H4B_1 109.9 . . ? C3_1 C4_1 H4B_1 109.9 . . ? H4A_1 C4_1 H4B_1 108.3 . . ? C4_1 C5_1 C6_1 113.1(2) . . ? C4_1 C5_1 H5A_1 109.0 . . ? C6_1 C5_1 H5A_1 109.0 . . ? C4_1 C5_1 H5B_1 109.0 . . ? C6_1 C5_1 H5B_1 109.0 . . ? H5A_1 C5_1 H5B_1 107.8 . . ? N1_1 C6_1 C7_1 107.5(2) . . ? N1_1 C6_1 C5_1 113.3(2) . . ? C7_1 C6_1 C5_1 116.6(2) . . ? N1_1 C6_1 C10_1 100.6(2) . . ? C7_1 C6_1 C10_1 105.1(2) . . ? C5_1 C6_1 C10_1 112.2(2) . . ? C8_1 C7_1 C6_1 103.7(2) . . ? C8_1 C7_1 H7A_1 111.0 . . ? C6_1 C7_1 H7A_1 111.0 . . ? C8_1 C7_1 H7B_1 111.0 . . ? C6_1 C7_1 H7B_1 111.0 . . ? H7A_1 C7_1 H7B_1 109.0 . . ? C7_1 C8_1 C9_1 102.8(2) . . ? C7_1 C8_1 H8A_1 111.2 . . ? C9_1 C8_1 H8A_1 111.2 . . ? C7_1 C8_1 H8B_1 111.2 . . ? C9_1 C8_1 H8B_1 111.2 . . ? H8A_1 C8_1 H8B_1 109.1 . . ? C10_1 C9_1 C8_1 103.7(2) . . ? C10_1 C9_1 H9A_1 111.0 . . ? C8_1 C9_1 H9A_1 111.0 . . ? C10_1 C9_1 H9B_1 111.0 . . ? C8_1 C9_1 H9B_1 111.0 . . ? H9A_1 C9_1 H9B_1 109.0 . . ? C9_1 C10_1 C11_1 117.4(2) . . ? C9_1 C10_1 C6_1 106.7(2) . . ? C11_1 C10_1 C6_1 102.8(2) . . ? C9_1 C10_1 H10_1 109.9 . . ? C11_1 C10_1 H10_1 109.9 . . ? C6_1 C10_1 H10_1 109.9 . . ? O1_1 C11_1 C13_1 108.7(2) . . ? O1_1 C11_1 C10_1 105.4(2) . . ? C13_1 C11_1 C10_1 113.9(2) . . ? O1_1 C11_1 H11_1 109.6 . . ? C13_1 C11_1 H11_1 109.6 . . ? C10_1 C11_1 H11_1 109.6 . . ? N2_1 C12_1 C1_1 177.3(3) . . ? N3_1 C13_1 C11_1 179.3(3) . . ? C11_2 O1_2 N1_2 99.16(18) . . ? C2_2 N1_2 O1_2 107.90(19) . . ? C2_2 N1_2 C6_2 115.5(2) . . ? O1_2 N1_2 C6_2 101.75(18) . . ? C12_2 C1_2 C2_2 111.1(2) . . ? C12_2 C1_2 H1A_2 109.4 . . ? C2_2 C1_2 H1A_2 109.4 . . ? C12_2 C1_2 H1B_2 109.4 . . ? C2_2 C1_2 H1B_2 109.4 . . ? H1A_2 C1_2 H1B_2 108.0 . . ? N1_2 C2_2 C3_2 115.4(2) . . ? N1_2 C2_2 C1_2 108.3(2) . . ? C3_2 C2_2 C1_2 112.9(2) . . ? N1_2 C2_2 H2_2 106.6 . . ? C3_2 C2_2 H2_2 106.6 . . ? C1_2 C2_2 H2_2 106.6 . . ? C4_2 C3_2 C2_2 108.7(2) . . ? C4_2 C3_2 H3A_2 110.0 . . ? C2_2 C3_2 H3A_2 110.0 . . ? C4_2 C3_2 H3B_2 110.0 . . ? C2_2 C3_2 H3B_2 110.0 . . ? H3A_2 C3_2 H3B_2 108.3 . . ? C5_2 C4_2 C3_2 109.1(2) . . ? C5_2 C4_2 H4A_2 109.9 . . ? C3_2 C4_2 H4A_2 109.9 . . ? C5_2 C4_2 H4B_2 109.9 . . ? C3_2 C4_2 H4B_2 109.9 . . ? H4A_2 C4_2 H4B_2 108.3 . . ? C4_2 C5_2 C6_2 113.1(2) . . ? C4_2 C5_2 H5A_2 109.0 . . ? C6_2 C5_2 H5A_2 109.0 . . ? C4_2 C5_2 H5B_2 109.0 . . ? C6_2 C5_2 H5B_2 109.0 . . ? H5A_2 C5_2 H5B_2 107.8 . . ? N1_2 C6_2 C7_2 107.7(2) . . ? N1_2 C6_2 C5_2 113.7(2) . . ? C7_2 C6_2 C5_2 115.8(2) . . ? N1_2 C6_2 C10_2 101.1(2) . . ? C7_2 C6_2 C10_2 105.2(2) . . ? C5_2 C6_2 C10_2 112.0(2) . . ? C6_2 C7_2 C8_2 103.7(2) . . ? C6_2 C7_2 H7A_2 111.0 . . ? C8_2 C7_2 H7A_2 111.0 . . ? C6_2 C7_2 H7B_2 111.0 . . ? C8_2 C7_2 H7B_2 111.0 . . ? H7A_2 C7_2 H7B_2 109.0 . . ? C9_2 C8_2 C7_2 102.6(2) . . ? C9_2 C8_2 H8A_2 111.3 . . ? C7_2 C8_2 H8A_2 111.3 . . ? C9_2 C8_2 H8B_2 111.3 . . ? C7_2 C8_2 H8B_2 111.3 . . ? H8A_2 C8_2 H8B_2 109.2 . . ? C8_2 C9_2 C10_2 104.2(2) . . ? C8_2 C9_2 H9A_2 110.9 . . ? C10_2 C9_2 H9A_2 110.9 . . ? C8_2 C9_2 H9B_2 110.9 . . ? C10_2 C9_2 H9B_2 110.9 . . ? H9A_2 C9_2 H9B_2 108.9 . . ? C9_2 C10_2 C11_2 117.3(2) . . ? C9_2 C10_2 C6_2 106.8(2) . . ? C11_2 C10_2 C6_2 102.6(2) . . ? C9_2 C10_2 H10_2 109.9 . . ? C11_2 C10_2 H10_2 109.9 . . ? C6_2 C10_2 H10_2 109.9 . . ? O1_2 C11_2 C13_2 108.7(2) . . ? O1_2 C11_2 C10_2 105.4(2) . . ? C13_2 C11_2 C10_2 114.0(2) . . ? O1_2 C11_2 H11_2 109.5 . . ? C13_2 C11_2 H11_2 109.5 . . ? C10_2 C11_2 H11_2 109.5 . . ? N2_2 C12_2 C1_2 177.9(3) . . ? N3_2 C13_2 C11_2 178.7(3) . . ? 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 C11_1 O1_1 N1_1 C2_1 177.32(19) . . . . ? C11_1 O1_1 N1_1 C6_1 55.3(2) . . . . ? O1_1 N1_1 C2_1 C3_1 -67.0(3) . . . . ? C6_1 N1_1 C2_1 C3_1 46.4(3) . . . . ? O1_1 N1_1 C2_1 C1_1 60.8(2) . . . . ? C6_1 N1_1 C2_1 C1_1 174.2(2) . . . . ? C12_1 C1_1 C2_1 N1_1 165.2(2) . . . . ? C12_1 C1_1 C2_1 C3_1 -66.1(3) . . . . ? N1_1 C2_1 C3_1 C4_1 -55.5(3) . . . . ? C1_1 C2_1 C3_1 C4_1 179.1(2) . . . . ? C2_1 C3_1 C4_1 C5_1 59.5(3) . . . . ? C3_1 C4_1 C5_1 C6_1 -56.9(3) . . . . ? C2_1 N1_1 C6_1 C7_1 89.4(3) . . . . ? O1_1 N1_1 C6_1 C7_1 -153.58(19) . . . . ? C2_1 N1_1 C6_1 C5_1 -41.0(3) . . . . ? O1_1 N1_1 C6_1 C5_1 76.0(2) . . . . ? C2_1 N1_1 C6_1 C10_1 -160.9(2) . . . . ? O1_1 N1_1 C6_1 C10_1 -43.9(2) . . . . ? C4_1 C5_1 C6_1 N1_1 47.2(3) . . . . ? C4_1 C5_1 C6_1 C7_1 -78.5(3) . . . . ? C4_1 C5_1 C6_1 C10_1 160.3(2) . . . . ? N1_1 C6_1 C7_1 C8_1 78.0(2) . . . . ? C5_1 C6_1 C7_1 C8_1 -153.5(2) . . . . ? C10_1 C6_1 C7_1 C8_1 -28.6(3) . . . . ? C6_1 C7_1 C8_1 C9_1 42.0(3) . . . . ? C7_1 C8_1 C9_1 C10_1 -38.8(3) . . . . ? C8_1 C9_1 C10_1 C11_1 -93.4(3) . . . . ? C8_1 C9_1 C10_1 C6_1 21.1(3) . . . . ? N1_1 C6_1 C10_1 C9_1 -107.0(2) . . . . ? C7_1 C6_1 C10_1 C9_1 4.6(3) . . . . ? C5_1 C6_1 C10_1 C9_1 132.2(2) . . . . ? N1_1 C6_1 C10_1 C11_1 17.0(2) . . . . ? C7_1 C6_1 C10_1 C11_1 128.6(2) . . . . ? C5_1 C6_1 C10_1 C11_1 -103.7(2) . . . . ? N1_1 O1_1 C11_1 C13_1 79.3(2) . . . . ? N1_1 O1_1 C11_1 C10_1 -43.2(2) . . . . ? C9_1 C10_1 C11_1 O1_1 132.7(2) . . . . ? C6_1 C10_1 C11_1 O1_1 16.1(3) . . . . ? C9_1 C10_1 C11_1 C13_1 13.6(3) . . . . ? C6_1 C10_1 C11_1 C13_1 -103.0(2) . . . . ? C2_1 C1_1 C12_1 N2_1 3(7) . . . . ? O1_1 C11_1 C13_1 N3_1 42(33) . . . . ? C10_1 C11_1 C13_1 N3_1 159(100) . . . . ? C11_2 O1_2 N1_2 C2_2 -177.33(19) . . . . ? C11_2 O1_2 N1_2 C6_2 -55.4(2) . . . . ? O1_2 N1_2 C2_2 C3_2 67.0(3) . . . . ? C6_2 N1_2 C2_2 C3_2 -46.0(3) . . . . ? O1_2 N1_2 C2_2 C1_2 -60.6(2) . . . . ? C6_2 N1_2 C2_2 C1_2 -173.6(2) . . . . ? C12_2 C1_2 C2_2 N1_2 -167.3(2) . . . . ? C12_2 C1_2 C2_2 C3_2 63.7(3) . . . . ? N1_2 C2_2 C3_2 C4_2 55.4(3) . . . . ? C1_2 C2_2 C3_2 C4_2 -179.3(2) . . . . ? C2_2 C3_2 C4_2 C5_2 -59.2(3) . . . . ? C3_2 C4_2 C5_2 C6_2 56.3(3) . . . . ? C2_2 N1_2 C6_2 C7_2 -89.7(2) . . . . ? O1_2 N1_2 C6_2 C7_2 153.77(19) . . . . ? C2_2 N1_2 C6_2 C5_2 40.0(3) . . . . ? O1_2 N1_2 C6_2 C5_2 -76.5(2) . . . . ? C2_2 N1_2 C6_2 C10_2 160.2(2) . . . . ? O1_2 N1_2 C6_2 C10_2 43.7(2) . . . . ? C4_2 C5_2 C6_2 N1_2 -46.0(3) . . . . ? C4_2 C5_2 C6_2 C7_2 79.4(3) . . . . ? C4_2 C5_2 C6_2 C10_2 -159.9(2) . . . . ? N1_2 C6_2 C7_2 C8_2 -79.0(2) . . . . ? C5_2 C6_2 C7_2 C8_2 152.5(2) . . . . ? C10_2 C6_2 C7_2 C8_2 28.2(3) . . . . ? C6_2 C7_2 C8_2 C9_2 -41.4(3) . . . . ? C7_2 C8_2 C9_2 C10_2 38.4(3) . . . . ? C8_2 C9_2 C10_2 C11_2 93.2(3) . . . . ? C8_2 C9_2 C10_2 C6_2 -21.1(3) . . . . ? N1_2 C6_2 C10_2 C9_2 107.5(2) . . . . ? C7_2 C6_2 C10_2 C9_2 -4.5(3) . . . . ? C5_2 C6_2 C10_2 C9_2 -131.1(2) . . . . ? N1_2 C6_2 C10_2 C11_2 -16.4(2) . . . . ? C7_2 C6_2 C10_2 C11_2 -128.4(2) . . . . ? C5_2 C6_2 C10_2 C11_2 104.9(2) . . . . ? N1_2 O1_2 C11_2 C13_2 -78.7(2) . . . . ? N1_2 O1_2 C11_2 C10_2 43.8(2) . . . . ? C9_2 C10_2 C11_2 O1_2 -133.7(2) . . . . ? C6_2 C10_2 C11_2 O1_2 -17.0(2) . . . . ? C9_2 C10_2 C11_2 C13_2 -14.5(3) . . . . ? C6_2 C10_2 C11_2 C13_2 102.1(2) . . . . ? C2_2 C1_2 C12_2 N2_2 -17(9) . . . . ? O1_2 C11_2 C13_2 N3_2 -60(14) . . . . ? C10_2 C11_2 C13_2 N3_2 -177(100) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.224 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.053 data_ah0320_cif _database_code_depnum_ccdc_archive 'CCDC 230766' _audit_creation_date 03-20-11 _audit_creation_method CRYSTALS_ver_12-03-99 _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment mixed #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 12.610(3) _cell_angle_alpha 90 _cell_length_b 12.464(3) _cell_angle_beta 107.01(3) _cell_length_c 16.763(3) _cell_angle_gamma 90 _cell_volume 2519.5(10) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 8 _chemical_formula_sum ' C13 H17 N3 O1 ' _chemical_formula_moiety ' C13 H17 N3 O1 ' _chemical_compound_source ; ? ; _chemical_formula_weight 231.30 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 5.10 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 240 _exptl_crystal_description ' needle ' _exptl_crystal_colour ' white ' _exptl_crystal_size_min 0.01 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 992.000 _exptl_absorpt_coefficient_mu 0.080 _diffrn_measurement_device_type ; Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_absorpt_correction_T_min 0.889 _exptl_absorpt_correction_T_max 0.996 _diffrn_ambient_temperature 240 _diffrn_reflns_number 21461 _reflns_number_total 5684 _diffrn_reflns_av_R_equivalents 0.03 # Number of reflections with Friedels Law is 5684 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5737 _diffrn_reflns_theta_min 5.123 _diffrn_reflns_theta_max 27.452 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.804 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -16 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _refine_diff_density_min -0.16 _refine_diff_density_max 0.22 _refine_ls_number_reflns 2637 _refine_ls_number_restraints 0 _refine_ls_number_parameters 307 #_refine_ls_R_factor_ref 0.0477 _refine_ls_wR_factor_ref 0.0443 _refine_ls_goodness_of_fit_ref 1.1747 #_reflns_number_all 5684 _refine_ls_R_factor_all 0.1194 _refine_ls_wR_factor_all 0.0581 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 2637 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_gt 0.0443 _refine_ls_shift/su_max 0.000186 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 A~i~ are: 1.76 1.51 1.44 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_refinement_flags _atom_site_attached_hydrogens O1 O 0.6551(1) 0.50349(9) 0.25124(8) 0.0480 1.0000 Uani . . O2 O 0.3449(1) 0.20685(9) 0.24537(8) 0.0467 1.0000 Uani . . N2 N 0.30145(12) 0.10438(11) 0.26235(9) 0.0443 1.0000 Uani . . N1 N 0.69687(13) 0.59896(11) 0.2209(1) 0.0467 1.0000 Uani . . C11 C 0.53655(17) 0.45534(16) 0.32907(13) 0.0544 1.0000 Uani . . C14 C 0.44281(15) 0.18272(14) 0.22012(12) 0.0461 1.0000 Uani . . C10 C 0.55486(15) 0.53472(14) 0.26957(12) 0.0447 1.0000 Uani . . C26 C 0.45692(17) 0.27450(16) 0.16860(13) 0.0527 1.0000 Uani . . C19 C 0.31110(15) 0.03830(14) 0.19194(12) 0.0461 1.0000 Uani . . C9 C 0.57213(16) 0.65267(13) 0.30014(12) 0.0461 1.0000 Uani . . C5 C 0.68224(16) 0.68108(14) 0.28077(12) 0.0484 1.0000 Uani . . C23 C 0.37184(16) 0.06950(15) 0.34551(12) 0.0489 1.0000 Uani . . C15 C 0.42088(15) 0.07316(14) 0.17547(12) 0.0469 1.0000 Uani . . C12 C 0.65290(16) 0.52344(17) 0.08029(12) 0.0541 1.0000 Uani . . C20 C 0.30186(17) -0.08176(14) 0.20944(14) 0.0556 1.0000 Uani . . C25 C 0.2406(2) 0.15293(15) 0.41238(13) 0.0565 1.0000 Uani . . C24 C 0.35492(17) 0.14831(16) 0.41093(13) 0.0544 1.0000 Uani . . C1 C 0.62906(17) 0.61480(15) 0.13378(12) 0.0513 1.0000 Uani . . C6 C 0.77272(18) 0.66591(16) 0.36553(14) 0.0618 1.0000 Uani . . C16 C 0.39367(18) 0.07902(16) 0.08063(13) 0.0588 1.0000 Uani . . C21 C 0.37068(18) -0.11760(15) 0.29569(16) 0.0625 1.0000 Uani . . N5 N 0.15129(19) 0.15726(16) 0.41462(14) 0.0789 1.0000 Uani . . C4 C 0.6888(2) 0.79478(16) 0.24742(15) 0.0666 1.0000 Uani . . C18 C 0.21956(16) 0.07132(16) 0.11147(13) 0.0556 1.0000 Uani . . C17 C 0.27741(19) 0.12561(17) 0.05404(14) 0.0620 1.0000 Uani . . N4 N 0.52142(18) 0.39129(17) 0.37317(13) 0.0757 1.0000 Uani . . C2 C 0.6528(2) 0.72488(18) 0.10426(15) 0.0695 1.0000 Uani . . C8 C 0.59706(19) 0.66863(16) 0.39373(13) 0.0597 1.0000 Uani . . C13 C 0.76968(19) 0.51662(18) 0.08339(13) 0.0581 1.0000 Uani . . C22 C 0.34460(18) -0.04641(16) 0.36043(14) 0.0603 1.0000 Uani . . N3 N 0.85958(18) 0.5098(2) 0.08490(14) 0.0890 1.0000 Uani . . C3 C 0.6211(2) 0.81079(17) 0.15773(16) 0.0773 1.0000 Uani . . C7 C 0.7165(2) 0.6296(2) 0.42816(15) 0.0724 1.0000 Uani . . N6 N 0.46798(17) 0.34536(15) 0.12903(13) 0.0682 1.0000 Uani . . H141 H 0.5148 0.1757 0.2672 0.0613 1.0000 Uiso . . H101 H 0.4838 0.5344 0.2206 0.0583 1.0000 Uiso . . H91 H 0.5027 0.6967 0.2719 0.0601 1.0000 Uiso . . H231 H 0.4532 0.0703 0.3476 0.0589 1.0000 Uiso . . H151 H 0.4886 0.0251 0.1972 0.0589 1.0000 Uiso . . H121 H 0.6071 0.5342 0.0203 0.0673 1.0000 Uiso . . H122 H 0.6295 0.4529 0.0999 0.0673 1.0000 Uiso . . H201 H 0.3241 -0.1246 0.1654 0.0683 1.0000 Uiso . . H202 H 0.2208 -0.0992 0.2028 0.0683 1.0000 Uiso . . H241 H 0.4041 0.1274 0.4679 0.0684 1.0000 Uiso . . H242 H 0.3786 0.2232 0.3984 0.0684 1.0000 Uiso . . H11 H 0.5471 0.6134 0.1292 0.0607 1.0000 Uiso . . H61 H 0.8154 0.7349 0.3835 0.0766 1.0000 Uiso . . H62 H 0.8301 0.6098 0.3597 0.0766 1.0000 Uiso . . H161 H 0.4491 0.1275 0.0630 0.0751 1.0000 Uiso . . H162 H 0.3969 0.0067 0.0544 0.0751 1.0000 Uiso . . H211 H 0.4523 -0.1107 0.3001 0.0808 1.0000 Uiso . . H212 H 0.3556 -0.1951 0.3056 0.0808 1.0000 Uiso . . H41 H 0.7689 0.8122 0.2526 0.0781 1.0000 Uiso . . H42 H 0.6627 0.8472 0.2838 0.0781 1.0000 Uiso . . H181 H 0.1649 0.1218 0.1273 0.0687 1.0000 Uiso . . H182 H 0.1764 0.0062 0.0846 0.0687 1.0000 Uiso . . H171 H 0.2786 0.2071 0.0616 0.0741 1.0000 Uiso . . H172 H 0.2371 0.1109 -0.0066 0.0741 1.0000 Uiso . . H21 H 0.7361 0.7300 0.1108 0.0868 1.0000 Uiso . . H22 H 0.6125 0.7349 0.0439 0.0868 1.0000 Uiso . . H81 H 0.5894 0.7457 0.4094 0.0751 1.0000 Uiso . . H82 H 0.5444 0.6245 0.4172 0.0751 1.0000 Uiso . . H221 H 0.3885 -0.0694 0.4195 0.0758 1.0000 Uiso . . H222 H 0.2631 -0.0524 0.3575 0.0758 1.0000 Uiso . . H31 H 0.6352 0.8851 0.1379 0.0958 1.0000 Uiso . . H32 H 0.5400 0.8052 0.1526 0.0958 1.0000 Uiso . . H71 H 0.7528 0.6616 0.4856 0.0919 1.0000 Uiso . . H72 H 0.7187 0.5488 0.4350 0.0919 1.0000 Uiso . . 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 O1 0.0531(8) 0.0343(6) 0.0573(8) 0.0013(6) 0.0174(6) 0.0018(5) O2 0.0503(7) 0.0324(6) 0.0588(8) -0.0010(5) 0.0180(6) -0.0006(5) N2 0.0423(8) 0.0342(7) 0.0549(9) -0.0004(7) 0.0118(7) -0.0024(6) N1 0.0507(9) 0.0364(8) 0.054(1) 0.0001(7) 0.0175(8) -0.0017(7) C11 0.0536(12) 0.0443(11) 0.0633(13) -0.002(1) 0.014(1) -0.0081(8) C14 0.045(1) 0.0391(9) 0.0541(11) -0.0022(9) 0.0143(9) -0.0050(8) C10 0.0434(11) 0.0384(9) 0.0518(11) -0.0002(8) 0.0131(8) 0.0005(8) C26 0.0540(12) 0.042(1) 0.0618(13) -0.0105(9) 0.016(1) -0.0135(9) C19 0.041(1) 0.0386(9) 0.0573(11) -0.0033(8) 0.0131(8) -0.0025(7) C9 0.0481(11) 0.0353(9) 0.0555(11) -0.0022(8) 0.0161(9) 0.0040(7) C5 0.0517(11) 0.0375(9) 0.0554(11) -0.0048(9) 0.0146(9) -0.0014(8) C23 0.0463(11) 0.046(1) 0.0532(12) 0.0044(9) 0.0132(9) 0.0029(8) C15 0.046(1) 0.0373(9) 0.0583(12) -0.0047(8) 0.0174(9) 0.0010(8) C12 0.0504(12) 0.0598(12) 0.0528(11) -0.0041(9) 0.0164(9) -0.0080(9) C20 0.0595(12) 0.0361(9) 0.0723(14) -0.0078(9) 0.021(1) -0.0059(8) C25 0.0630(15) 0.0492(11) 0.0556(12) -0.0025(9) 0.015(1) -0.005(1) C24 0.0503(12) 0.0614(12) 0.0504(12) 0.0002(9) 0.0130(9) -0.0059(9) C1 0.0540(11) 0.048(1) 0.0517(12) 0.0046(9) 0.0158(9) 0.0011(8) C6 0.0550(13) 0.0590(12) 0.0645(14) -0.0111(11) 0.007(1) -0.005(1) C16 0.0661(14) 0.0519(11) 0.0633(13) -0.012(1) 0.0265(11) -0.009(1) C21 0.0620(13) 0.0360(9) 0.0902(16) 0.009(1) 0.0232(12) 0.0037(9) N5 0.0619(14) 0.0814(14) 0.0972(16) -0.0040(11) 0.0291(12) 0.001(1) C4 0.0846(17) 0.0383(11) 0.0788(16) -0.004(1) 0.0269(13) -0.012(1) C18 0.0493(12) 0.0553(11) 0.0582(12) -0.0105(9) 0.0094(9) -0.0096(9) C17 0.0692(15) 0.0562(12) 0.0547(12) -0.005(1) 0.0087(11) -0.013(1) N4 0.0823(14) 0.0627(12) 0.0810(14) 0.0117(11) 0.0221(11) -0.017(1) C2 0.0919(18) 0.0532(12) 0.0673(14) 0.0115(11) 0.0293(13) 0.0028(11) C8 0.0739(15) 0.0497(11) 0.0562(13) -0.0101(9) 0.0199(11) -0.001(1) C13 0.0562(15) 0.0662(13) 0.0514(12) -0.007(1) 0.015(1) -0.006(1) C22 0.0582(13) 0.0474(11) 0.0750(14) 0.015(1) 0.0187(11) 0.0039(9) N3 0.0494(13) 0.132(2) 0.0843(15) -0.0272(14) 0.0174(11) -0.0057(12) C3 0.105(2) 0.0407(11) 0.0877(18) 0.0126(12) 0.0301(16) 0.0023(12) C7 0.0791(17) 0.0682(14) 0.0587(14) 0.0005(11) 0.0027(12) -0.0052(12) N6 0.0831(14) 0.050(1) 0.0727(12) -0.0043(9) 0.025(1) -0.0216(9) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C10 . 1.439(2) yes O1 . N1 . 1.4523(18) yes O2 . C14 . 1.449(2) yes O2 . N2 . 1.4505(18) yes N2 . C23 . 1.482(2) yes N2 . C19 . 1.473(2) yes N1 . C1 . 1.474(3) yes N1 . C5 . 1.482(2) yes C11 . N4 . 1.141(3) yes C11 . C10 . 1.470(3) yes C14 . H141 . 1.018 no C14 . C15 . 1.543(2) yes C14 . C26 . 1.475(3) yes C10 . H101 . 1.023 no C10 . C9 . 1.551(2) yes C26 . N6 . 1.137(3) yes C19 . C18 . 1.552(3) yes C19 . C20 . 1.536(3) yes C19 . C15 . 1.551(3) yes C9 . H91 . 1.024 no C9 . C8 . 1.520(3) yes C9 . C5 . 1.556(3) yes C5 . C4 . 1.534(3) yes C5 . C6 . 1.552(3) yes C23 . H231 . 1.017 no C23 . C22 . 1.522(3) yes C23 . C24 . 1.533(3) yes C15 . H151 . 1.020 no C15 . C16 . 1.527(3) yes C12 . H122 . 1.013 no C12 . H121 . 1.012 no C12 . C13 . 1.461(3) yes C12 . C1 . 1.533(3) yes C20 . H202 . 1.019 no C20 . H201 . 1.015 no C20 . C21 . 1.520(3) yes C25 . N5 . 1.139(3) yes C25 . C24 . 1.450(3) yes C24 . H242 . 1.020 no C24 . H241 . 1.009 no C1 . H11 . 1.014 no C1 . C2 . 1.518(3) yes C6 . H62 . 1.031 no C6 . H61 . 1.012 no C6 . C7 . 1.498(3) yes C16 . H162 . 1.008 no C16 . H161 . 1.031 no C16 . C17 . 1.518(3) yes C21 . H212 . 1.007 no C21 . H211 . 1.013 no C21 . C22 . 1.511(3) yes C4 . H42 . 1.011 no C4 . H41 . 1.013 no C4 . C3 . 1.509(3) yes C18 . H182 . 1.007 no C18 . H181 . 1.023 no C18 . C17 . 1.526(3) yes C17 . H172 . 1.011 no C17 . H171 . 1.023 no C2 . H22 . 0.998 no C2 . H21 . 1.025 no C2 . C3 . 1.523(3) yes C8 . H82 . 1.025 no C8 . H81 . 1.008 no C8 . C7 . 1.527(3) yes C13 . N3 . 1.130(3) yes C22 . H222 . 1.018 no C22 . H221 . 1.024 no C3 . H32 . 1.003 no C3 . H31 . 1.017 no C7 . H72 . 1.013 no C7 . H71 . 1.018 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C10 . O1 . N1 . 106.53(11) yes C14 . O2 . N2 . 106.12(11) yes C23 . N2 . C19 . 114.99(14) yes C23 . N2 . O2 . 106.63(13) yes C19 . N2 . O2 . 102.15(12) yes C1 . N1 . C5 . 115.30(14) yes C1 . N1 . O1 . 106.97(13) yes C5 . N1 . O1 . 101.47(12) yes N4 . C11 . C10 . 177.7(2) yes H141 . C14 . C15 . 107.023 no H141 . C14 . C26 . 106.722 no C15 . C14 . C26 . 115.95(16) yes H141 . C14 . O2 . 115.741 no C15 . C14 . O2 . 106.16(14) yes C26 . C14 . O2 . 105.61(15) yes H101 . C10 . C9 . 105.930 no H101 . C10 . O1 . 116.402 no C9 . C10 . O1 . 106.24(14) yes H101 . C10 . C11 . 105.534 no C9 . C10 . C11 . 116.65(16) yes O1 . C10 . C11 . 106.55(14) yes N6 . C26 . C14 . 179.8(2) yes C18 . C19 . C20 . 110.22(15) yes C18 . C19 . C15 . 104.28(15) yes C20 . C19 . C15 . 115.38(15) yes C18 . C19 . N2 . 109.46(14) yes C20 . C19 . N2 . 111.28(15) yes C15 . C19 . N2 . 105.85(13) yes H91 . C9 . C8 . 107.320 no H91 . C9 . C5 . 118.374 no C8 . C9 . C5 . 104.94(16) yes H91 . C9 . C10 . 109.694 no C8 . C9 . C10 . 115.57(15) yes C5 . C9 . C10 . 101.21(14) yes C4 . C5 . C6 . 110.04(16) yes C4 . C5 . N1 . 111.13(16) yes C6 . C5 . N1 . 109.39(15) yes C4 . C5 . C9 . 115.61(16) yes C6 . C5 . C9 . 104.07(16) yes N1 . C5 . C9 . 106.23(14) yes H231 . C23 . C22 . 106.095 no H231 . C23 . C24 . 108.618 no C22 . C23 . C24 . 113.90(16) yes H231 . C23 . N2 . 110.548 no C22 . C23 . N2 . 109.33(15) yes C24 . C23 . N2 . 108.33(15) yes H151 . C15 . C16 . 108.008 no H151 . C15 . C19 . 118.036 no C16 . C15 . C19 . 104.97(15) yes H151 . C15 . C14 . 109.559 no C16 . C15 . C14 . 114.62(15) yes C19 . C15 . C14 . 101.80(14) yes H122 . C12 . H121 . 107.552 no H122 . C12 . C13 . 108.919 no H121 . C12 . C13 . 108.635 no H122 . C12 . C1 . 109.280 no H121 . C12 . C1 . 109.309 no C13 . C12 . C1 . 113.00(16) yes H202 . C20 . H201 . 106.840 no H202 . C20 . C21 . 108.485 no H201 . C20 . C21 . 109.572 no H202 . C20 . C19 . 108.472 no H201 . C20 . C19 . 108.736 no C21 . C20 . C19 . 114.46(17) yes N5 . C25 . C24 . 179.0(2) yes H242 . C24 . H241 . 107.193 no H242 . C24 . C25 . 108.595 no H241 . C24 . C25 . 109.485 no H242 . C24 . C23 . 109.208 no H241 . C24 . C23 . 109.596 no C25 . C24 . C23 . 112.61(16) yes H11 . C1 . C2 . 106.574 no H11 . C1 . N1 . 110.837 no C2 . C1 . N1 . 109.36(17) yes H11 . C1 . C12 . 108.223 no C2 . C1 . C12 . 112.94(17) yes N1 . C1 . C12 . 108.90(15) yes H62 . C6 . H61 . 106.122 no H62 . C6 . C7 . 110.530 no H61 . C6 . C7 . 111.572 no H62 . C6 . C5 . 110.098 no H61 . C6 . C5 . 110.672 no C7 . C6 . C5 . 107.87(18) yes H162 . C16 . H161 . 106.422 no H162 . C16 . C17 . 111.875 no H161 . C16 . C17 . 111.641 no H162 . C16 . C15 . 112.649 no H161 . C16 . C15 . 111.233 no C17 . C16 . C15 . 103.15(16) yes H212 . C21 . H211 . 107.809 no H212 . C21 . C22 . 110.748 no H211 . C21 . C22 . 109.126 no H212 . C21 . C20 . 110.826 no H211 . C21 . C20 . 109.198 no C22 . C21 . C20 . 109.10(16) yes H42 . C4 . H41 . 107.564 no H42 . C4 . C3 . 109.021 no H41 . C4 . C3 . 108.458 no H42 . C4 . C5 . 108.415 no H41 . C4 . C5 . 108.973 no C3 . C4 . C5 . 114.21(17) yes H182 . C18 . H181 . 107.102 no H182 . C18 . C17 . 111.792 no H181 . C18 . C17 . 111.914 no H182 . C18 . C19 . 109.979 no H181 . C18 . C19 . 108.901 no C17 . C18 . C19 . 107.14(16) yes H172 . C17 . H171 . 106.774 no H172 . C17 . C16 . 112.560 no H171 . C17 . C16 . 111.443 no H172 . C17 . C18 . 111.213 no H171 . C17 . C18 . 110.807 no C16 . C17 . C18 . 104.13(17) yes H22 . C2 . H21 . 107.589 no H22 . C2 . C3 . 111.410 no H21 . C2 . C3 . 109.304 no H22 . C2 . C1 . 110.665 no H21 . C2 . C1 . 108.363 no C3 . C2 . C1 . 109.43(18) yes H82 . C8 . H81 . 106.841 no H82 . C8 . C7 . 111.208 no H81 . C8 . C7 . 111.373 no H82 . C8 . C9 . 111.390 no H81 . C8 . C9 . 112.727 no C7 . C8 . C9 . 103.39(17) yes N3 . C13 . C12 . 178.8(2) yes H222 . C22 . H221 . 106.199 no H222 . C22 . C21 . 110.596 no H221 . C22 . C21 . 111.179 no H222 . C22 . C23 . 109.544 no H221 . C22 . C23 . 109.868 no C21 . C22 . C23 . 109.41(17) yes H32 . C3 . H31 . 107.858 no H32 . C3 . C4 . 109.962 no H31 . C3 . C4 . 110.132 no H32 . C3 . C2 . 109.743 no H31 . C3 . C2 . 110.245 no C4 . C3 . C2 . 108.89(19) yes H72 . C7 . H71 . 107.021 no H72 . C7 . C6 . 112.148 no H71 . C7 . C6 . 111.759 no H72 . C7 . C8 . 110.519 no H71 . C7 . C8 . 110.661 no C6 . C7 . C8 . 104.79(19) yes