# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_section_title ; Naphthalene proton sponges as hydride donors: diverse appearances of the tert-amino-effect ; _publ_contact_author_name 'Pozharskii, Alexander' _publ_contact_author_email apozharskii@sfedu.ru loop_ _publ_author_name A.Pozharskii M.Povalyakhina A.Degtyarev O.Ryabtsova ; V.Ozeryanskii ; O.Dyablo A.Tkachuk O.Kazheva A.Chekhlov O.Dyachenko #===END data_a _database_code_depnum_ccdc_archive 'CCDC 720578' #TrackingRef 't-Amino-Fig1-to-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 N2 O2' _chemical_formula_weight 270.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.333(2) _cell_length_b 10.094(2) _cell_length_c 11.308(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.94(2) _cell_angle_gamma 90.00 _cell_volume 1430.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2635 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2508 _reflns_number_gt 1678 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0690P)^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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2508 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 1.214 _refine_ls_restrained_S_all 1.214 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.006 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 0.4329(2) -0.1593(3) 0.6512(3) 0.1769(14) Uani 1 1 d . . . O2 O 0.1278(2) 0.5707(2) 0.1010(2) 0.1282(8) Uani 1 1 d . . . N1 N 0.24842(19) -0.0377(2) 0.30423(19) 0.0889(7) Uani 1 1 d . . . N2 N 0.12479(14) 0.17825(19) 0.17168(15) 0.0698(6) Uani 1 1 d . . . C1 C 0.29762(18) 0.0576(3) 0.3943(2) 0.0694(7) Uani 1 1 d . . . C2 C 0.3628(2) 0.0207(3) 0.5143(2) 0.0891(9) Uani 1 1 d . . . C3 C 0.4149(2) 0.1171(5) 0.6040(3) 0.1078(13) Uani 1 1 d . . . C4 C 0.4130(2) 0.2454(5) 0.5734(3) 0.1016(11) Uani 1 1 d . . . C5 C 0.35019(17) 0.2897(3) 0.4530(2) 0.0758(7) Uani 1 1 d . . . C6 C 0.28271(16) 0.1970(2) 0.36467(18) 0.0614(6) Uani 1 1 d . . . C7 C 0.20480(16) 0.2550(2) 0.25415(18) 0.0597(6) Uani 1 1 d . . . C8 C 0.20862(19) 0.3907(2) 0.2313(2) 0.0718(7) Uani 1 1 d . . . C9 C 0.2879(3) 0.4720(3) 0.3113(3) 0.0910(9) Uani 1 1 d . . . C10 C 0.3535(3) 0.4235(3) 0.4213(3) 0.0914(9) Uani 1 1 d . . . C11 C 0.2755(4) -0.0446(5) 0.1919(3) 0.1157(12) Uani 1 1 d . . . C12 C 0.1934(4) -0.1533(3) 0.3321(4) 0.1402(14) Uani 1 1 d . . . H12A H 0.1974 -0.1502 0.4183 0.210 Uiso 1 1 calc R . . H12B H 0.2268 -0.2329 0.3173 0.210 Uiso 1 1 calc R . . H12C H 0.1199 -0.1522 0.2783 0.210 Uiso 1 1 calc R . . C13 C 0.0982(3) 0.1863(4) 0.0359(2) 0.1003(10) Uani 1 1 d . . . C14 C 0.0491(3) 0.1112(4) 0.2142(4) 0.0959(9) Uani 1 1 d . . . C15 C 0.3928(3) -0.1175(5) 0.5467(4) 0.1257(14) Uani 1 1 d . . . C16 C 0.1217(3) 0.4582(3) 0.1342(3) 0.0955(9) Uani 1 1 d . . . H3 H 0.453(3) 0.092(3) 0.680(3) 0.109(10) Uiso 1 1 d . . . H4 H 0.456(3) 0.314(3) 0.636(3) 0.124(10) Uiso 1 1 d . . . H9 H 0.291(3) 0.566(3) 0.288(3) 0.116(11) Uiso 1 1 d . . . H10 H 0.399(2) 0.486(3) 0.472(3) 0.102(9) Uiso 1 1 d . . . H15 H 0.3798 -0.1774 0.4805 0.152 Uiso 1 1 calc R . . H16 H 0.054(3) 0.400(3) 0.102(3) 0.126(12) Uiso 1 1 d . . . H111 H 0.216(3) -0.062(3) 0.127(4) 0.116(12) Uiso 1 1 d . . . H112 H 0.327(3) -0.112(3) 0.201(3) 0.127(11) Uiso 1 1 d . . . H113 H 0.315(2) 0.040(3) 0.176(2) 0.099(10) Uiso 1 1 d . . . H131 H 0.027(2) 0.231(3) -0.004(3) 0.100(9) Uiso 1 1 d . . . H132 H 0.098(2) 0.082(3) 0.012(2) 0.106(9) Uiso 1 1 d . . . H133 H 0.159(3) 0.240(3) 0.018(3) 0.120(11) Uiso 1 1 d . . . H141 H -0.016(3) 0.154(3) 0.184(3) 0.141(14) Uiso 1 1 d . . . H142 H 0.037(3) 0.010(4) 0.185(3) 0.131(12) Uiso 1 1 d . . . H143 H 0.072(2) 0.112(3) 0.310(3) 0.121(11) Uiso 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 0.149(2) 0.243(4) 0.132(2) 0.117(2) 0.0394(17) 0.065(2) O2 0.1441(19) 0.0924(16) 0.151(2) 0.0362(14) 0.0539(16) 0.0317(14) N1 0.1184(18) 0.0730(15) 0.0757(14) -0.0012(11) 0.0335(13) 0.0090(13) N2 0.0685(11) 0.0869(14) 0.0484(10) -0.0039(9) 0.0127(9) -0.0064(10) C1 0.0673(13) 0.0902(18) 0.0525(13) 0.0086(13) 0.0227(11) 0.0093(13) C2 0.0739(15) 0.133(3) 0.0615(17) 0.0339(18) 0.0240(14) 0.0227(17) C3 0.0680(18) 0.198(4) 0.0487(18) 0.020(2) 0.0087(14) 0.007(2) C4 0.0712(17) 0.170(4) 0.0568(17) -0.019(2) 0.0125(14) -0.013(2) C5 0.0621(13) 0.107(2) 0.0592(14) -0.0196(14) 0.0218(11) -0.0083(14) C6 0.0589(12) 0.0808(16) 0.0440(11) -0.0042(11) 0.0170(10) 0.0015(12) C7 0.0630(12) 0.0686(15) 0.0506(12) -0.0058(10) 0.0232(10) 0.0012(11) C8 0.0777(15) 0.0690(16) 0.0752(15) -0.0029(13) 0.0345(13) 0.0073(14) C9 0.100(2) 0.073(2) 0.111(2) -0.0162(18) 0.050(2) -0.0059(17) C10 0.0829(19) 0.097(2) 0.100(2) -0.039(2) 0.0388(17) -0.0245(18) C11 0.121(3) 0.139(3) 0.086(2) -0.023(2) 0.033(2) 0.032(3) C12 0.188(4) 0.077(2) 0.149(3) 0.0053(19) 0.050(3) -0.004(2) C13 0.101(2) 0.127(3) 0.0557(16) -0.0008(16) 0.0048(15) 0.009(2) C14 0.079(2) 0.108(3) 0.097(2) -0.010(2) 0.0252(17) -0.0179(19) C15 0.106(2) 0.173(4) 0.102(3) 0.068(3) 0.040(2) 0.045(2) C16 0.106(2) 0.079(2) 0.106(2) 0.0213(18) 0.0431(19) 0.0244(19) _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 C15 1.195(4) . ? O2 C16 1.207(4) . ? N1 C1 1.392(3) . ? N1 C11 1.436(4) . ? N1 C12 1.468(4) . ? N2 C7 1.389(3) . ? N2 C14 1.428(3) . ? N2 C13 1.455(3) . ? C1 C2 1.390(3) . ? C1 C6 1.444(3) . ? C2 C3 1.406(5) . ? C2 C15 1.463(5) . ? C3 C4 1.339(5) . ? C4 C5 1.406(4) . ? C5 C10 1.402(4) . ? C5 C6 1.439(3) . ? C6 C7 1.448(3) . ? C7 C8 1.398(3) . ? C8 C9 1.399(4) . ? C8 C16 1.465(4) . ? C9 C10 1.345(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 C1 N1 C11 118.8(3) . . ? C1 N1 C12 122.5(2) . . ? C11 N1 C12 116.5(3) . . ? C7 N2 C14 120.5(2) . . ? C7 N2 C13 122.1(2) . . ? C14 N2 C13 115.8(3) . . ? C2 C1 N1 120.7(2) . . ? C2 C1 C6 118.6(2) . . ? N1 C1 C6 120.73(19) . . ? C1 C2 C3 120.6(3) . . ? C1 C2 C15 121.8(3) . . ? C3 C2 C15 117.0(3) . . ? C4 C3 C2 121.4(3) . . ? C3 C4 C5 120.7(3) . . ? C10 C5 C4 119.6(3) . . ? C10 C5 C6 121.0(2) . . ? C4 C5 C6 119.4(3) . . ? C5 C6 C1 117.9(2) . . ? C5 C6 C7 115.5(2) . . ? C1 C6 C7 126.5(2) . . ? N2 C7 C8 119.4(2) . . ? N2 C7 C6 121.0(2) . . ? C8 C7 C6 119.6(2) . . ? C9 C8 C7 121.5(2) . . ? C9 C8 C16 116.2(3) . . ? C7 C8 C16 121.7(2) . . ? C10 C9 C8 119.7(3) . . ? C9 C10 C5 121.3(3) . . ? O1 C15 C2 125.2(5) . . ? O2 C16 C8 123.5(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 N1 C1 C2 -117.0(3) . . . . ? C12 N1 C1 C2 45.8(4) . . . . ? C11 N1 C1 C6 62.5(3) . . . . ? C12 N1 C1 C6 -134.7(3) . . . . ? N1 C1 C2 C3 178.1(2) . . . . ? C6 C1 C2 C3 -1.4(3) . . . . ? N1 C1 C2 C15 7.5(4) . . . . ? C6 C1 C2 C15 -172.0(2) . . . . ? C1 C2 C3 C4 -7.2(4) . . . . ? C15 C2 C3 C4 163.9(3) . . . . ? C2 C3 C4 C5 6.0(5) . . . . ? C3 C4 C5 C10 -176.9(3) . . . . ? C3 C4 C5 C6 3.7(4) . . . . ? C10 C5 C6 C1 168.7(2) . . . . ? C4 C5 C6 C1 -11.9(3) . . . . ? C10 C5 C6 C7 -12.0(3) . . . . ? C4 C5 C6 C7 167.4(2) . . . . ? C2 C1 C6 C5 10.6(3) . . . . ? N1 C1 C6 C5 -168.91(19) . . . . ? C2 C1 C6 C7 -168.6(2) . . . . ? N1 C1 C6 C7 11.9(3) . . . . ? C14 N2 C7 C8 -117.9(3) . . . . ? C13 N2 C7 C8 47.4(3) . . . . ? C14 N2 C7 C6 60.7(3) . . . . ? C13 N2 C7 C6 -134.0(3) . . . . ? C5 C6 C7 N2 -170.17(17) . . . . ? C1 C6 C7 N2 9.1(3) . . . . ? C5 C6 C7 C8 8.5(3) . . . . ? C1 C6 C7 C8 -172.3(2) . . . . ? N2 C7 C8 C9 -179.7(2) . . . . ? C6 C7 C8 C9 1.6(3) . . . . ? N2 C7 C8 C16 9.5(3) . . . . ? C6 C7 C8 C16 -169.2(2) . . . . ? C7 C8 C9 C10 -8.9(4) . . . . ? C16 C8 C9 C10 162.4(2) . . . . ? C8 C9 C10 C5 5.4(4) . . . . ? C4 C5 C10 C9 -174.1(2) . . . . ? C6 C5 C10 C9 5.4(4) . . . . ? C1 C2 C15 O1 -166.8(3) . . . . ? C3 C2 C15 O1 22.3(5) . . . . ? C9 C8 C16 O2 18.4(4) . . . . ? C7 C8 C16 O2 -170.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.130 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.027 data_to _database_code_depnum_ccdc_archive 'CCDC 801823' #TrackingRef 't-Amino-Fig1-to-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 N6, 0.25(C2 H7 N), 0.75(C2 H3 N) ' _chemical_formula_sum 'C24 H22 N7' _chemical_formula_weight 408.49 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6455(7) _cell_length_b 12.9280(13) _cell_length_c 12.9430(13) _cell_angle_alpha 101.997(2) _cell_angle_beta 90.461(2) _cell_angle_gamma 94.532(2) _cell_volume 1083.94(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 322 _cell_measurement_theta_min 3 _cell_measurement_theta_max 26 _exptl_crystal_description plate _exptl_crystal_colour grey _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 430 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.958 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 "Bruker APEX II CCD area detector'" _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10008 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4202 _reflns_number_gt 3262 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0608P)^2^+0.6073P] 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 4202 _refine_ls_number_parameters 317 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1327 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.007 _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 N1 N -0.26852(15) -0.23465(8) 0.21878(8) 0.0171(2) Uani 1 1 d . . . N2 N -0.21133(15) -0.42094(8) 0.28996(8) 0.0179(2) Uani 1 1 d . . . N3 N -0.08028(19) 0.12682(9) 0.20227(10) 0.0323(3) Uani 1 1 d . . . N4 N -0.63576(19) -0.06490(11) 0.12012(11) 0.0392(3) Uani 1 1 d . . . N5 N -0.39045(19) -0.69103(10) 0.49072(10) 0.0334(3) Uani 1 1 d . . . N6 N 0.15634(17) -0.60440(9) 0.35508(9) 0.0275(3) Uani 1 1 d . . . C1 C -0.23232(17) -0.29633(9) 0.11760(9) 0.0158(3) Uani 1 1 d . . . C2 C -0.19009(17) -0.24696(9) 0.03370(10) 0.0173(3) Uani 1 1 d . . . C3 C -0.17585(18) -0.30762(10) -0.06980(10) 0.0188(3) Uani 1 1 d . . . H3A H -0.1440 -0.2737 -0.1250 0.023 Uiso 1 1 calc R . . C4 C -0.20833(17) -0.41510(10) -0.08950(9) 0.0181(3) Uani 1 1 d . . . H4A H -0.2096 -0.4536 -0.1587 0.022 Uiso 1 1 calc R . . C5 C -0.24027(17) -0.46887(9) -0.00580(9) 0.0165(3) Uani 1 1 d . . . C6 C -0.27311(17) -0.58076(10) -0.02892(10) 0.0179(3) Uani 1 1 d . . . H6A H -0.2711 -0.6178 -0.0986 0.021 Uiso 1 1 calc R . . C7 C -0.30753(17) -0.63455(9) 0.04957(10) 0.0177(3) Uani 1 1 d . . . H7A H -0.3401 -0.7075 0.0329 0.021 Uiso 1 1 calc R . . C8 C -0.29438(17) -0.58077(9) 0.15629(10) 0.0167(3) Uani 1 1 d . . . C9 C -0.24929(17) -0.47157(9) 0.18304(9) 0.0157(3) Uani 1 1 d . . . C10 C -0.23980(17) -0.41093(9) 0.10076(9) 0.0158(3) Uani 1 1 d . . . C11 C -0.46213(19) -0.25382(10) 0.26788(10) 0.0222(3) Uani 1 1 d . . . H11A H -0.5046 -0.3282 0.2504 0.033 Uiso 1 1 calc R . . H11B H -0.5616 -0.2148 0.2422 0.033 Uiso 1 1 calc R . . H11C H -0.4469 -0.2310 0.3432 0.033 Uiso 1 1 calc R . . C12 C -0.18866(19) -0.12583(9) 0.23902(10) 0.0204(3) Uani 1 1 d . . . H12A H -0.0427 -0.1227 0.2460 0.024 Uiso 1 1 calc R . . H12B H -0.2393 -0.0890 0.3055 0.024 Uiso 1 1 calc R . . C13 C -0.24625(19) -0.06756(10) 0.14934(10) 0.0209(3) Uani 1 1 d . . . C14 C -0.15578(19) -0.12788(10) 0.04675(10) 0.0213(3) Uani 1 1 d . . . H14A H -0.2163 -0.1069 -0.0134 0.026 Uiso 1 1 calc R . . H14B H -0.0118 -0.1080 0.0475 0.026 Uiso 1 1 calc R . . C15 C -0.4669(2) -0.06605(10) 0.13518(11) 0.0251(3) Uani 1 1 d . . . C16 C -0.1570(2) 0.04291(10) 0.17736(11) 0.0242(3) Uani 1 1 d . . . C17 C -0.01725(19) -0.35941(10) 0.31849(10) 0.0234(3) Uani 1 1 d . . . H17A H 0.0245 -0.3255 0.2620 0.035 Uiso 1 1 calc R . . H17B H 0.0821 -0.4059 0.3306 0.035 Uiso 1 1 calc R . . H17C H -0.0310 -0.3065 0.3816 0.035 Uiso 1 1 calc R . . C18 C -0.2926(2) -0.47623(10) 0.36795(10) 0.0203(3) Uani 1 1 d . . . H18A H -0.4384 -0.4751 0.3676 0.024 Uiso 1 1 calc R . . H18B H -0.2410 -0.4397 0.4374 0.024 Uiso 1 1 calc R . . C19 C -0.23672(19) -0.59452(10) 0.34697(10) 0.0197(3) Uani 1 1 d . . . C20 C -0.32871(19) -0.64837(9) 0.23728(10) 0.0200(3) Uani 1 1 d . . . H20A H -0.2697 -0.7152 0.2131 0.024 Uiso 1 1 calc R . . H20B H -0.4727 -0.6639 0.2436 0.024 Uiso 1 1 calc R . . C21 C -0.0151(2) -0.59993(10) 0.35062(10) 0.0213(3) Uani 1 1 d . . . C22 C -0.3222(2) -0.64912(10) 0.42805(10) 0.0241(3) Uani 1 1 d . . . N1S N -0.1467(5) -0.0275(2) 0.5486(2) 0.0429(7) Uani 0.50 1 d P . . H1SA H -0.0492 -0.0728 0.5384 0.051 Uiso 0.25 1 d PR . . C1S C -0.2429(9) -0.0328(5) 0.5624(5) 0.0248(7) Uani 0.25 1 d PU . . C2S C -0.3144(6) -0.0556(3) 0.6008(3) 0.0547(11) Uani 0.50 1 d P . . H2SA H -0.3006 -0.1223 0.6204 0.082 Uiso 0.50 1 d PR . . H2SB H -0.3291 -0.0019 0.6632 0.082 Uiso 0.50 1 d PR . . H2SC H -0.4315 -0.0614 0.5554 0.082 Uiso 0.50 1 d PR . . N1A N 0.0438(8) 0.1021(3) 0.4579(3) 0.0790(15) Uani 0.50 1 d P . . C1A C -0.0522(6) 0.0842(2) 0.4826(3) 0.0448(10) Uani 0.50 1 d P . . C2A C -0.1974(5) 0.0606(3) 0.5250(2) 0.0389(9) Uani 0.50 1 d P . . H2AA H -0.1629 0.0504 0.5941 0.047 Uiso 0.50 1 d PR . . H2AC H -0.2853 0.1271 0.5294 0.047 Uiso 0.50 1 d PR . . H2AB H -0.2679 -0.0032 0.4854 0.047 Uiso 0.50 1 d PR . . C1B C -0.1123(9) 0.0673(5) 0.5163(5) 0.0208(7) Uani 0.25 1 d PU . . H1BA H 0.0148 0.0726 0.4822 0.031 Uiso 0.25 1 d PR . . H1BB H -0.2203 0.0672 0.4666 0.031 Uiso 0.25 1 d PR . . H1BC H -0.1179 0.1267 0.5744 0.031 Uiso 0.25 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0211(5) 0.0135(5) 0.0164(5) 0.0021(4) 0.0009(4) 0.0022(4) N2 0.0219(5) 0.0175(5) 0.0138(5) 0.0021(4) -0.0016(4) 0.0023(4) N3 0.0382(7) 0.0199(5) 0.0390(7) 0.0065(5) 0.0046(5) 0.0020(5) N4 0.0283(6) 0.0421(7) 0.0499(8) 0.0138(6) -0.0024(6) 0.0089(6) N5 0.0408(7) 0.0323(6) 0.0320(6) 0.0152(5) 0.0083(5) 0.0098(5) N6 0.0271(6) 0.0321(6) 0.0247(6) 0.0071(5) -0.0006(5) 0.0072(5) C1 0.0128(5) 0.0170(5) 0.0169(6) 0.0017(5) -0.0014(4) 0.0019(4) C2 0.0126(5) 0.0186(6) 0.0212(6) 0.0050(5) -0.0006(5) 0.0026(5) C3 0.0159(5) 0.0248(6) 0.0171(6) 0.0072(5) 0.0018(5) 0.0032(5) C4 0.0155(5) 0.0241(6) 0.0136(6) 0.0009(5) -0.0003(5) 0.0039(5) C5 0.0106(5) 0.0198(6) 0.0191(6) 0.0032(5) -0.0005(4) 0.0046(4) C6 0.0136(5) 0.0194(6) 0.0182(6) -0.0027(5) -0.0014(5) 0.0043(5) C7 0.0138(5) 0.0149(5) 0.0232(6) 0.0005(5) -0.0019(5) 0.0026(5) C8 0.0135(5) 0.0166(5) 0.0201(6) 0.0030(5) 0.0000(5) 0.0042(4) C9 0.0142(5) 0.0162(5) 0.0165(6) 0.0016(5) -0.0004(4) 0.0049(4) C10 0.0117(5) 0.0186(6) 0.0168(6) 0.0024(5) -0.0005(4) 0.0033(4) C11 0.0258(6) 0.0184(6) 0.0210(6) 0.0001(5) 0.0049(5) 0.0040(5) C12 0.0238(6) 0.0154(6) 0.0211(6) 0.0019(5) -0.0019(5) 0.0020(5) C13 0.0209(6) 0.0169(6) 0.0261(6) 0.0070(5) -0.0001(5) 0.0023(5) C14 0.0212(6) 0.0197(6) 0.0240(6) 0.0065(5) 0.0006(5) 0.0030(5) C15 0.0268(7) 0.0210(6) 0.0289(7) 0.0075(5) 0.0013(5) 0.0051(5) C16 0.0252(6) 0.0206(6) 0.0286(7) 0.0078(5) 0.0040(5) 0.0062(5) C17 0.0261(6) 0.0191(6) 0.0241(6) 0.0030(5) -0.0061(5) 0.0017(5) C18 0.0260(6) 0.0174(6) 0.0180(6) 0.0037(5) 0.0010(5) 0.0057(5) C19 0.0209(6) 0.0196(6) 0.0205(6) 0.0066(5) 0.0007(5) 0.0063(5) C20 0.0216(6) 0.0150(6) 0.0236(6) 0.0044(5) -0.0006(5) 0.0033(5) C21 0.0283(7) 0.0210(6) 0.0159(6) 0.0054(5) -0.0004(5) 0.0053(5) C22 0.0271(6) 0.0227(6) 0.0242(7) 0.0063(5) 0.0017(5) 0.0083(5) N1S 0.0657(17) 0.0312(13) 0.0245(13) -0.0144(11) -0.0236(12) 0.0163(13) C1S 0.0238(9) 0.0259(9) 0.0245(10) 0.0049(7) 0.0012(7) 0.0015(7) C2S 0.049(2) 0.063(2) 0.044(2) -0.0025(19) 0.0025(17) -0.0130(19) N1A 0.160(4) 0.0438(19) 0.0262(16) 0.0023(14) -0.027(2) -0.016(2) C1A 0.096(3) 0.0110(13) 0.0261(16) -0.0061(12) -0.0333(17) 0.0256(15) C2A 0.0451(18) 0.0419(18) 0.0235(15) -0.0085(14) -0.0130(14) 0.0077(16) C1B 0.0212(9) 0.0207(9) 0.0207(10) 0.0047(7) 0.0003(7) 0.0016(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.4177(15) . ? N1 C12 1.4338(15) . ? N1 C11 1.4660(16) . ? N2 C9 1.4138(15) . ? N2 C18 1.4385(17) . ? N2 C17 1.4632(16) . ? N3 C16 1.1425(17) . ? N4 C15 1.1390(18) . ? N5 C22 1.1431(18) . ? N6 C21 1.1470(17) . ? C1 C2 1.3891(18) . ? C1 C10 1.4487(17) . ? C2 C3 1.4127(17) . ? C2 C14 1.5121(17) . ? C3 C4 1.3589(18) . ? C3 H3A 0.9300 . ? C4 C5 1.4126(18) . ? C4 H4A 0.9300 . ? C5 C6 1.4137(17) . ? C5 C10 1.4260(16) . ? C6 C7 1.3566(18) . ? C6 H6A 0.9300 . ? C7 C8 1.4099(17) . ? C7 H7A 0.9300 . ? C8 C9 1.3896(16) . ? C8 C20 1.5060(18) . ? C9 C10 1.4467(18) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.5695(18) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C16 1.4732(17) . ? C13 C15 1.4786(18) . ? C13 C14 1.5457(18) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.5713(17) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C22 1.4753(19) . ? C19 C21 1.4807(18) . ? C19 C20 1.5433(17) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? N1S C1S 0.667(6) . ? N1S C2S 1.372(5) . ? N1S C1B 1.378(7) . ? N1S H1SA 0.8999 . ? C1S C2S 0.776(7) . ? C2S H2SA 0.9600 . ? C2S H2SB 0.9601 . ? C2S H2SC 0.9599 . ? N1A C1A 0.757(6) . ? C1A C2A 1.165(5) . ? C2A H2AC 1.0684 . ? C2A H2AB 0.9600 . ? C1B H1BA 0.9601 . ? C1B H1BB 0.9601 . ? C1B H1BC 0.9602 . ? 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 C1 N1 C12 116.25(10) . . ? C1 N1 C11 118.68(9) . . ? C12 N1 C11 114.87(10) . . ? C9 N2 C18 116.49(10) . . ? C9 N2 C17 118.29(10) . . ? C18 N2 C17 115.52(10) . . ? C2 C1 N1 120.01(11) . . ? C2 C1 C10 119.56(10) . . ? N1 C1 C10 120.43(11) . . ? C1 C2 C3 120.57(11) . . ? C1 C2 C14 123.01(11) . . ? C3 C2 C14 116.42(11) . . ? C4 C3 C2 120.60(12) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 120.62(11) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C4 C5 C6 119.23(11) . . ? C4 C5 C10 120.37(11) . . ? C6 C5 C10 120.39(11) . . ? C7 C6 C5 120.63(11) . . ? C7 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C6 C7 C8 120.53(11) . . ? C6 C7 H7A 119.7 . . ? C8 C7 H7A 119.7 . . ? C9 C8 C7 120.72(12) . . ? C9 C8 C20 122.99(11) . . ? C7 C8 C20 116.28(10) . . ? C8 C9 N2 119.85(11) . . ? C8 C9 C10 119.49(10) . . ? N2 C9 C10 120.65(10) . . ? C5 C10 C9 117.26(11) . . ? C5 C10 C1 117.31(11) . . ? C9 C10 C1 125.42(10) . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 C13 112.68(10) . . ? N1 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? N1 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C16 C13 C15 108.35(11) . . ? C16 C13 C14 110.91(11) . . ? C15 C13 C14 110.06(10) . . ? C16 C13 C12 108.41(10) . . ? C15 C13 C12 112.71(11) . . ? C14 C13 C12 106.41(10) . . ? C2 C14 C13 112.46(11) . . ? C2 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? C2 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? N4 C15 C13 177.27(15) . . ? N3 C16 C13 176.37(15) . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N2 C18 C19 112.10(10) . . ? N2 C18 H18A 109.2 . . ? C19 C18 H18A 109.2 . . ? N2 C18 H18B 109.2 . . ? C19 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C22 C19 C21 107.28(11) . . ? C22 C19 C20 109.88(10) . . ? C21 C19 C20 111.51(10) . . ? C22 C19 C18 110.84(10) . . ? C21 C19 C18 111.04(10) . . ? C20 C19 C18 106.33(10) . . ? C8 C20 C19 112.75(10) . . ? C8 C20 H20A 109.0 . . ? C19 C20 H20A 109.0 . . ? C8 C20 H20B 109.0 . . ? C19 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? N6 C21 C19 178.89(14) . . ? N5 C22 C19 179.26(15) . . ? C2S N1S C1B 124.7(4) . . ? N1S C1S C2S 143.6(11) . . ? N1A C1A C2A 176.6(5) . . ? N1S C1B H1BA 112.2 . . ? N1S C1B H1BB 104.7 . . ? H1BA C1B H1BB 109.5 . . ? N1S C1B H1BC 111.4 . . ? N1A C1B H1BC 102.1 . . ? H1BA C1B H1BC 109.5 . . ? H1BB C1B H1BC 109.5 . . ? 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 C12 N1 C1 C2 -22.26(16) . . . . ? C11 N1 C1 C2 121.27(12) . . . . ? C12 N1 C1 C10 157.98(11) . . . . ? C11 N1 C1 C10 -58.48(15) . . . . ? N1 C1 C2 C3 -172.95(10) . . . . ? C10 C1 C2 C3 6.80(17) . . . . ? N1 C1 C2 C14 7.46(17) . . . . ? C10 C1 C2 C14 -172.78(11) . . . . ? C1 C2 C3 C4 1.71(18) . . . . ? C14 C2 C3 C4 -178.68(11) . . . . ? C2 C3 C4 C5 -5.32(18) . . . . ? C3 C4 C5 C6 -179.83(11) . . . . ? C3 C4 C5 C10 0.29(17) . . . . ? C4 C5 C6 C7 -178.91(11) . . . . ? C10 C5 C6 C7 0.96(17) . . . . ? C5 C6 C7 C8 -5.37(18) . . . . ? C6 C7 C8 C9 1.07(18) . . . . ? C6 C7 C8 C20 -178.08(11) . . . . ? C7 C8 C9 N2 -171.93(11) . . . . ? C20 C8 C9 N2 7.17(17) . . . . ? C7 C8 C9 C10 7.48(17) . . . . ? C20 C8 C9 C10 -173.42(11) . . . . ? C18 N2 C9 C8 -22.48(16) . . . . ? C17 N2 C9 C8 122.09(12) . . . . ? C18 N2 C9 C10 158.12(11) . . . . ? C17 N2 C9 C10 -57.31(15) . . . . ? C4 C5 C10 C9 -172.80(10) . . . . ? C6 C5 C10 C9 7.33(16) . . . . ? C4 C5 C10 C1 7.93(16) . . . . ? C6 C5 C10 C1 -171.94(10) . . . . ? C8 C9 C10 C5 -11.43(16) . . . . ? N2 C9 C10 C5 167.97(10) . . . . ? C8 C9 C10 C1 167.78(11) . . . . ? N2 C9 C10 C1 -12.82(18) . . . . ? C2 C1 C10 C5 -11.38(16) . . . . ? N1 C1 C10 C5 168.38(10) . . . . ? C2 C1 C10 C9 169.41(11) . . . . ? N1 C1 C10 C9 -10.83(18) . . . . ? C1 N1 C12 C13 50.18(14) . . . . ? C11 N1 C12 C13 -94.74(12) . . . . ? N1 C12 C13 C16 -179.83(10) . . . . ? N1 C12 C13 C15 60.24(14) . . . . ? N1 C12 C13 C14 -60.48(13) . . . . ? C1 C2 C14 C13 -20.87(16) . . . . ? C3 C2 C14 C13 159.53(11) . . . . ? C16 C13 C14 C2 161.71(11) . . . . ? C15 C13 C14 C2 -78.41(13) . . . . ? C12 C13 C14 C2 44.00(13) . . . . ? C9 N2 C18 C19 50.53(14) . . . . ? C17 N2 C18 C19 -95.03(12) . . . . ? N2 C18 C19 C22 -179.95(10) . . . . ? N2 C18 C19 C21 60.91(13) . . . . ? N2 C18 C19 C20 -60.56(13) . . . . ? C9 C8 C20 C19 -20.60(16) . . . . ? C7 C8 C20 C19 158.54(10) . . . . ? C22 C19 C20 C8 164.16(10) . . . . ? C21 C19 C20 C8 -77.02(13) . . . . ? C18 C19 C20 C8 44.15(13) . . . . ? N1A N1S C1S C2S 42.3(19) 2_556 . . . ? C2A N1S C1S C2S -149.1(16) . . . . ? C1B N1S C1S C2S -147.0(15) . . . . ? C1A N1S C1S C2S 50(2) 2_556 . . . ? C1A N1S C1S C2S -155.3(13) . . . . ? N1A N1S C1S C2A -168.7(5) 2_556 . . . ? C2S N1S C1S C2A 149.1(16) . . . . ? C1B N1S C1S C2A 2.0(4) . . . . ? C1A N1S C1S C2A -161.1(11) 2_556 . . . ? C1A N1S C1S C2A -6.2(4) . . . . ? C2A N1S C1S N1A 168.7(5) . . . 2_556 ? C2S N1S C1S N1A -42.3(19) . . . 2_556 ? C1B N1S C1S N1A 170.7(8) . . . 2_556 ? C1A N1S C1S N1A 7.5(7) 2_556 . . 2_556 ? C1A N1S C1S N1A 162.5(8) . . . 2_556 ? N1A N1S C1S C1B -170.7(8) 2_556 . . . ? C2A N1S C1S C1B -2.0(4) . . . . ? C2S N1S C1S C1B 147.0(15) . . . . ? C1A N1S C1S C1B -163.2(13) 2_556 . . . ? C1A N1S C1S C1B -8.3(3) . . . . ? C2A C1S C2S N1S -131(2) . . . . ? N1A C1S C2S N1S 27.3(13) 2_556 . . . ? C1B C1S C2S N1S -107(3) . . . . ? N1A N1S C2S C1S -142.8(17) 2_556 . . . ? C2A N1S C2S C1S 31.4(17) . . . . ? C1B N1S C2S C1S 38.9(17) . . . . ? C1A N1S C2S C1S -145.7(17) 2_556 . . . ? C1A N1S C2S C1S 32.6(17) . . . . ? N1S N1A C1A C1B 57(3) 2_556 . . . ? C1S N1A C1A C1B 54(3) 2_556 . . . ? C2A N1A C1A C1B -57(10) . . . . ? C1B N1A C1A N1S -57(3) . . . 2_556 ? C1S N1A C1A N1S -3.8(3) 2_556 . . 2_556 ? C2A N1A C1A N1S -114(11) . . . 2_556 ? N1S N1A C1A N1S 10.7(8) 2_556 . . . ? C1B N1A C1A N1S -47(2) . . . . ? C1S N1A C1A N1S 7.0(9) 2_556 . . . ? C2A N1A C1A N1S -104(11) . . . . ? C1S N1S C1A C1B 33.7(14) . . . . ? N1A N1S C1A C1B -163.5(12) 2_556 . . . ? C2A N1S C1A C1B 23.4(12) . . . . ? C2S N1S C1A C1B 21.5(13) . . . . ? C1A N1S C1A C1B -159.8(13) 2_556 . . . ? C1S N1S C1A N1A -174.6(9) . . . . ? N1A N1S C1A N1A -11.8(9) 2_556 . . . ? C2A N1S C1A N1A 175.2(8) . . . . ? C2S N1S C1A N1A 173.3(6) . . . . ? C1B N1S C1A N1A 151.8(15) . . . . ? C1A N1S C1A N1A -8.0(6) 2_556 . . . ? C1S N1S C1A C2A 10.3(7) . . . . ? N1A N1S C1A C2A 173.0(4) 2_556 . . . ? C2S N1S C1A C2A -1.9(4) . . . . ? C1B N1S C1A C2A -23.4(12) . . . . ? C1A N1S C1A C2A 176.8(4) 2_556 . . . ? C1S N1S C1A N1S -166.5(7) . . . 2_556 ? N1A N1S C1A N1S -3.8(3) 2_556 . . 2_556 ? C2A N1S C1A N1S -176.8(4) . . . 2_556 ? C2S N1S C1A N1S -178.7(4) . . . 2_556 ? C1B N1S C1A N1S 159.8(13) . . . 2_556 ? C1A N1S C1A N1S 0.0 2_556 . . 2_556 ? N1S C1A C2A C1B 46(2) 2_556 . . . ? N1S C1A C2A C1B 42(2) . . . . ? C1B C1A C2A N1S -42(2) . . . . ? N1S C1A C2A N1S 4.4(5) 2_556 . . . ? C1B C1A C2A C1S -47(2) . . . . ? N1S C1A C2A C1S -0.9(7) 2_556 . . . ? N1S C1A C2A C1S -5.3(4) . . . . ? C1B C1A C2A N1A 66(11) . . . . ? N1S C1A C2A N1A 112(11) 2_556 . . . ? N1S C1A C2A N1A 107(11) . . . . ? C1S N1S C2A C1B 175.4(9) . . . . ? N1A N1S C2A C1B -27.8(11) 2_556 . . . ? C2S N1S C2A C1B 165.3(7) . . . . ? C1A N1S C2A C1B -17.5(8) 2_556 . . . ? C1A N1S C2A C1B -13.5(7) . . . . ? C1S N1S C2A C1A -171.2(6) . . . . ? N1A N1S C2A C1A -14.3(8) 2_556 . . . ? C2S N1S C2A C1A 178.7(3) . . . . ? C1B N1S C2A C1A 13.5(7) . . . . ? C1A N1S C2A C1A -4.0(5) 2_556 . . . ? N1A N1S C2A C1S 156.8(10) 2_556 . . . ? C2S N1S C2A C1S -10.1(6) . . . . ? C1B N1S C2A C1S -175.4(9) . . . . ? C1A N1S C2A C1S 167.1(7) 2_556 . . . ? C1A N1S C2A C1S 171.2(6) . . . . ? C1S N1S C2A N1A -172.4(6) . . . . ? N1A N1S C2A N1A -15.6(8) 2_556 . . . ? C2S N1S C2A N1A 177.4(2) . . . . ? C1B N1S C2A N1A 12.2(7) . . . . ? C1A N1S C2A N1A -5.3(3) 2_556 . . . ? C1A N1S C2A N1A -1.3(2) . . . . ? N1S C1S C2A C1B -5.0(10) . . . . ? C2S C1S C2A C1B 146.1(13) . . . . ? N1A C1S C2A C1B -12.6(9) 2_556 . . . ? N1S C1S C2A C1A 11.0(8) . . . . ? C2S C1S C2A C1A 162.1(10) . . . . ? N1A C1S C2A C1A 3.5(6) 2_556 . . . ? C1B C1S C2A C1A 16.0(8) . . . . ? C2S C1S C2A N1S 151.1(16) . . . . ? N1A C1S C2A N1S -7.6(3) 2_556 . . . ? C1B C1S C2A N1S 5.0(10) . . . . ? N1S C1S C2A N1A 9.5(7) . . . . ? C2S C1S C2A N1A 160.6(10) . . . . ? N1A C1S C2A N1A 1.9(6) 2_556 . . . ? C1B C1S C2A N1A 14.5(7) . . . . ? C1A N1A C2A C1B 111(11) . . . . ? N1S N1A C2A C1B 45(2) 2_556 . . . ? C1S N1A C2A C1B 40(2) 2_556 . . . ? N1S N1A C2A C1A -66(11) 2_556 . . . ? C1B N1A C2A C1A -111(11) . . . . ? C1S N1A C2A C1A -71(11) 2_556 . . . ? C1A N1A C2A N1S 73(11) . . . . ? N1S N1A C2A N1S 6.9(4) 2_556 . . . ? C1B N1A C2A N1S -38(2) . . . . ? C1S N1A C2A N1S 2.3(4) 2_556 . . . ? C1A N1A C2A C1S 68(11) . . . . ? N1S N1A C2A C1S 2.4(5) 2_556 . . . ? C1B N1A C2A C1S -43(2) . . . . ? C1S N1A C2A C1S -2.2(7) 2_556 . . . ? N1S C2A C1B C1A 139.0(19) . . . . ? C1S C2A C1B C1A 141.3(17) . . . . ? N1A C2A C1B C1A -3.5(6) . . . . ? C1A C2A C1B N1S -139.0(19) . . . . ? C1S C2A C1B N1S 2.4(5) . . . . ? N1A C2A C1B N1S -142.5(19) . . . . ? C1A C2A C1B N1A 3.5(6) . . . . ? N1S C2A C1B N1A 142.5(19) . . . . ? C1S C2A C1B N1A 144.9(17) . . . . ? C1A C2A C1B C1S -141.3(17) . . . . ? N1S C2A C1B C1S -2.4(5) . . . . ? N1A C2A C1B C1S -144.9(17) . . . . ? N1A C1A C1B C2A 170.9(16) . . . . ? N1S C1A C1B C2A -142.9(17) 2_556 . . . ? N1S C1A C1B C2A -120(2) . . . . ? N1A C1A C1B N1S -70(3) . . . . ? C2A C1A C1B N1S 120(3) . . . . ? N1S C1A C1B N1S -23.3(14) 2_556 . . . ? C2A C1A C1B N1A -170.9(16) . . . . ? N1S C1A C1B N1A 46(2) 2_556 . . . ? N1S C1A C1B N1A 70(3) . . . . ? N1A C1A C1B C1S -92(3) . . . . ? C2A C1A C1B C1S 97(3) . . . . ? N1S C1A C1B C1S -46(2) 2_556 . . . ? N1S C1A C1B C1S -22.9(10) . . . . ? C1S N1S C1B C2A -4.9(10) . . . . ? N1A N1S C1B C2A 164.4(6) 2_556 . . . ? C2S N1S C1B C2A -17.7(9) . . . . ? C1A N1S C1B C2A 165.8(7) 2_556 . . . ? C1A N1S C1B C2A 144.9(17) . . . . ? C1S N1S C1B C1A -149.8(13) . . . . ? N1A N1S C1B C1A 19.5(15) 2_556 . . . ? C2A N1S C1B C1A -144.9(17) . . . . ? C2S N1S C1B C1A -162.7(11) . . . . ? C1A N1S C1B C1A 20.8(13) 2_556 . . . ? C1S N1S C1B N1A -162.8(8) . . . . ? N1A N1S C1B N1A 6.5(10) 2_556 . . . ? C2A N1S C1B N1A -158.0(12) . . . . ? C2S N1S C1B N1A -175.7(5) . . . . ? C1A N1S C1B N1A 7.8(7) 2_556 . . . ? C1A N1S C1B N1A -13.0(8) . . . . ? N1A N1S C1B C1S 169.3(9) 2_556 . . . ? C2A N1S C1B C1S 4.9(10) . . . . ? C2S N1S C1B C1S -12.9(6) . . . . ? C1A N1S C1B C1S 170.6(7) 2_556 . . . ? C1A N1S C1B C1S 149.8(13) . . . . ? C1A N1A C1B C2A -12(2) . . . . ? N1S N1A C1B C2A -136(2) 2_556 . . . ? C1S N1A C1B C2A -142.9(19) 2_556 . . . ? N1S N1A C1B C1A -124(3) 2_556 . . . ? C1S N1A C1B C1A -131(3) 2_556 . . . ? C2A N1A C1B C1A 12(2) . . . . ? C1A N1A C1B N1S 119(3) . . . . ? N1S N1A C1B N1S -4.9(7) 2_556 . . . ? C1S N1A C1B N1S -11.5(8) 2_556 . . . ? C2A N1A C1B N1S 131(2) . . . . ? C1A N1A C1B C1S 107(3) . . . . ? N1S N1A C1B C1S -17.6(11) 2_556 . . . ? C1S N1A C1B C1S -24.2(13) 2_556 . . . ? C2A N1A C1B C1S 119(3) . . . . ? N1S C1S C1B C2A 173.9(12) . . . . ? C2S C1S C1B C2A -54.1(19) . . . . ? N1A C1S C1B C2A 168.0(9) 2_556 . . . ? N1S C1S C1B C1A 49(2) . . . . ? C2S C1S C1B C1A -179(2) . . . . ? C2A C1S C1B C1A -125(2) . . . . ? N1A C1S C1B C1A 42.9(19) 2_556 . . . ? C2S C1S C1B N1S 132(2) . . . . ? C2A C1S C1B N1S -173.9(12) . . . . ? N1A C1S C1B N1S -5.9(5) 2_556 . . . ? N1S C1S C1B N1A 27.1(12) . . . . ? C2S C1S C1B N1A 159.0(15) . . . . ? C2A C1S C1B N1A -146.9(17) . . . . ? N1A C1S C1B N1A 21.1(12) 2_556 . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.367 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.047 _publ_section_references ; Bruker, Programs APEX II, version 2.0-1; SAINT, version 7.23A; SADABS, version 2004/1; XPREP, version 2005/2; SHELXTL, version 6.1. Bruker AXS Inc., Madison, WI, USA, 2005. G.M. Sheldrick, Programs SHELXS97 (crystal structure solution) and SHELXL97 (crystal structure refinement), University of Gottingen, Germany, 1997. ; #===END data_fin _database_code_depnum_ccdc_archive 'CCDC 801824' #TrackingRef 't-Amino-Fig1-to-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H32 N4' _chemical_formula_sum 'C20 H32 N4' _chemical_formula_weight 328.50 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P c' _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 34.582(2) _cell_length_b 10.1577(6) _cell_length_c 8.3390(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.8910(10) _cell_angle_gamma 90.00 _cell_volume 2925.5(3) _cell_formula_units_Z 6 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 819 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.119 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 "Bruker APEX II CCD area detector'" _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29486 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -44 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.00 _reflns_number_total 12592 _reflns_number_gt 7117 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0345P)^2^+0.2100P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(17) _refine_ls_number_reflns 12592 _refine_ls_number_parameters 673 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1034 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1043 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.004 _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 N11 N 0.19893(6) 0.1760(2) 0.7019(2) 0.0502(6) Uani 1 1 d . . . N12 N 0.11905(6) 0.1732(2) 0.6387(2) 0.0474(6) Uani 1 1 d . . . N13 N 0.02787(6) 0.3456(2) 0.3625(3) 0.0531(6) Uani 1 1 d . . . N14 N 0.30534(6) 0.2254(3) 0.4909(3) 0.0647(7) Uani 1 1 d . . . C11 C 0.20103(8) 0.2481(3) 0.5562(3) 0.0437(7) Uani 1 1 d . . . C12 C 0.23649(8) 0.2917(3) 0.5084(3) 0.0529(7) Uani 1 1 d . . . C13 C 0.23920(9) 0.3685(3) 0.3705(4) 0.0618(8) Uani 1 1 d . . . H13A H 0.2631 0.4026 0.3450 0.074 Uiso 1 1 calc R . . C14 C 0.20733(9) 0.3943(3) 0.2729(3) 0.0589(8) Uani 1 1 d . . . H14A H 0.2096 0.4444 0.1805 0.071 Uiso 1 1 calc R . . C15 C 0.17084(8) 0.3450(2) 0.3119(3) 0.0459(6) Uani 1 1 d . . . C16 C 0.13840(8) 0.3697(3) 0.2040(3) 0.0551(8) Uani 1 1 d . . . H16A H 0.1420 0.4136 0.1080 0.066 Uiso 1 1 calc R . . C17 C 0.10282(8) 0.3305(3) 0.2387(3) 0.0553(7) Uani 1 1 d . . . H17A H 0.0823 0.3432 0.1640 0.066 Uiso 1 1 calc R . . C18 C 0.09617(7) 0.2705(3) 0.3867(3) 0.0463(7) Uani 1 1 d . . . C19 C 0.12687(8) 0.2396(2) 0.4938(3) 0.0409(6) Uani 1 1 d . . . C110 C 0.16596(8) 0.2756(2) 0.4581(3) 0.0402(7) Uani 1 1 d . . . C111 C 0.19579(9) 0.0353(3) 0.6916(4) 0.0740(9) Uani 1 1 d . . . H11A H 0.1826 0.0115 0.5918 0.111 Uiso 1 1 calc R . . H11B H 0.1815 0.0032 0.7793 0.111 Uiso 1 1 calc R . . H11C H 0.2212 -0.0029 0.6970 0.111 Uiso 1 1 calc R . . C112 C 0.21489(9) 0.2276(3) 0.8522(3) 0.0712(9) Uani 1 1 d . . . H11D H 0.2195 0.3203 0.8415 0.107 Uiso 1 1 calc R . . H11E H 0.2389 0.1838 0.8806 0.107 Uiso 1 1 calc R . . H11F H 0.1969 0.2132 0.9346 0.107 Uiso 1 1 calc R . . C113 C 0.11814(9) 0.2487(3) 0.7837(3) 0.0660(8) Uani 1 1 d . . . H11G H 0.1355 0.3220 0.7780 0.099 Uiso 1 1 calc R . . H11H H 0.1259 0.1942 0.8736 0.099 Uiso 1 1 calc R . . H11I H 0.0923 0.2804 0.7964 0.099 Uiso 1 1 calc R . . C114 C 0.09906(9) 0.0483(3) 0.6349(4) 0.0668(8) Uani 1 1 d . . . H11J H 0.1001 0.0104 0.5297 0.100 Uiso 1 1 calc R . . H11K H 0.0725 0.0615 0.6599 0.100 Uiso 1 1 calc R . . H11L H 0.1113 -0.0101 0.7125 0.100 Uiso 1 1 calc R . . C115 C 0.27366(9) 0.2531(4) 0.5985(3) 0.0602(9) Uani 1 1 d . . . H11M H 0.2816 0.3237 0.6713 0.072 Uiso 1 1 calc R . . H11N H 0.2691 0.1754 0.6625 0.072 Uiso 1 1 calc R . . C116 C 0.29695(10) 0.1090(4) 0.3947(4) 0.0916(11) Uani 1 1 d . . . H11O H 0.3182 0.0915 0.3281 0.137 Uiso 1 1 calc R . . H11P H 0.2739 0.1233 0.3282 0.137 Uiso 1 1 calc R . . H11Q H 0.2932 0.0351 0.4640 0.137 Uiso 1 1 calc R . . C117 C 0.34122(10) 0.2090(5) 0.5839(4) 0.0882(13) Uani 1 1 d . . . H11R H 0.3619 0.1957 0.5131 0.132 Uiso 1 1 calc R . . H11S H 0.3393 0.1340 0.6531 0.132 Uiso 1 1 calc R . . H11T H 0.3463 0.2864 0.6476 0.132 Uiso 1 1 calc R . . C118 C 0.05430(8) 0.2473(3) 0.4289(3) 0.0573(8) Uani 1 1 d . . . H11U H 0.0461 0.1614 0.3895 0.069 Uiso 1 1 calc R . . H11V H 0.0530 0.2468 0.5448 0.069 Uiso 1 1 calc R . . C119 C 0.03523(10) 0.4736(3) 0.4344(4) 0.0822(10) Uani 1 1 d . . . H11W H 0.0614 0.4994 0.4180 0.123 Uiso 1 1 calc R . . H11X H 0.0313 0.4692 0.5474 0.123 Uiso 1 1 calc R . . H11Y H 0.0178 0.5371 0.3853 0.123 Uiso 1 1 calc R . . C120 C -0.01183(9) 0.3062(4) 0.3909(5) 0.0790(11) Uani 1 1 d . . . H12A H -0.0294 0.3736 0.3523 0.118 Uiso 1 1 calc R . . H12B H -0.0145 0.2937 0.5040 0.118 Uiso 1 1 calc R . . H12C H -0.0177 0.2253 0.3352 0.118 Uiso 1 1 calc R . . N21 N 0.54730(7) 0.3260(2) 0.0018(3) 0.0477(6) Uani 1 1 d . . . N22 N 0.46793(7) 0.3234(2) -0.0738(3) 0.0497(6) Uani 1 1 d . . . N23 N 0.63457(7) 0.1451(3) 0.2870(3) 0.0625(7) Uani 1 1 d . . . N24 N 0.36079(7) 0.2762(3) 0.1266(3) 0.0639(7) Uani 1 1 d . . . C21 C 0.53861(8) 0.2619(3) 0.1456(3) 0.0407(7) Uani 1 1 d . . . C22 C 0.56824(9) 0.2317(3) 0.2590(3) 0.0493(8) Uani 1 1 d . . . C23 C 0.55946(9) 0.1748(3) 0.4070(4) 0.0601(9) Uani 1 1 d . . . H23A H 0.5790 0.1651 0.4869 0.072 Uiso 1 1 calc R . . C24 C 0.52338(9) 0.1342(3) 0.4350(3) 0.0549(8) Uani 1 1 d . . . H24A H 0.5186 0.0932 0.5317 0.066 Uiso 1 1 calc R . . C25 C 0.49301(8) 0.1531(3) 0.3197(3) 0.0471(7) Uani 1 1 d . . . C26 C 0.45567(9) 0.1064(3) 0.3521(4) 0.0558(8) Uani 1 1 d . . . H26A H 0.4522 0.0593 0.4459 0.067 Uiso 1 1 calc R . . C27 C 0.42522(9) 0.1287(3) 0.2506(4) 0.0599(9) Uani 1 1 d . . . H27A H 0.4013 0.0917 0.2707 0.072 Uiso 1 1 calc R . . C28 C 0.42896(8) 0.2075(3) 0.1137(3) 0.0499(8) Uani 1 1 d . . . C29 C 0.46508(8) 0.2522(3) 0.0697(3) 0.0429(7) Uani 1 1 d . . . C210 C 0.49903(8) 0.2241(3) 0.1744(3) 0.0411(7) Uani 1 1 d . . . C211 C 0.56797(10) 0.4479(3) 0.0051(4) 0.0682(9) Uani 1 1 d . . . H21B H 0.5659 0.4890 0.1080 0.102 Uiso 1 1 calc R . . H21C H 0.5572 0.5049 -0.0773 0.102 Uiso 1 1 calc R . . H21D H 0.5947 0.4316 -0.0131 0.102 Uiso 1 1 calc R . . C212 C 0.54965(9) 0.2500(3) -0.1431(3) 0.0697(9) Uani 1 1 d . . . H21E H 0.5353 0.1697 -0.1334 0.105 Uiso 1 1 calc R . . H21F H 0.5763 0.2299 -0.1601 0.105 Uiso 1 1 calc R . . H21G H 0.5389 0.2998 -0.2325 0.105 Uiso 1 1 calc R . . C213 C 0.47112(10) 0.4653(3) -0.0629(4) 0.0724(9) Uani 1 1 d . . . H21H H 0.4871 0.4884 0.0305 0.109 Uiso 1 1 calc R . . H21I H 0.4458 0.5029 -0.0547 0.109 Uiso 1 1 calc R . . H21J H 0.4826 0.4987 -0.1571 0.109 Uiso 1 1 calc R . . C214 C 0.45310(9) 0.2707(4) -0.2239(3) 0.0671(9) Uani 1 1 d . . . H21K H 0.4524 0.1764 -0.2174 0.101 Uiso 1 1 calc R . . H21L H 0.4696 0.2967 -0.3076 0.101 Uiso 1 1 calc R . . H21M H 0.4274 0.3037 -0.2472 0.101 Uiso 1 1 calc R . . C215 C 0.61063(8) 0.2530(3) 0.2273(4) 0.0534(8) Uani 1 1 d . . . H21N H 0.6134 0.2623 0.1127 0.064 Uiso 1 1 calc R . . H21O H 0.6195 0.3340 0.2786 0.064 Uiso 1 1 calc R . . C216 C 0.67544(10) 0.1760(5) 0.2749(5) 0.0872(12) Uani 1 1 d . . . H21P H 0.6817 0.2534 0.3368 0.131 Uiso 1 1 calc R . . H21Q H 0.6807 0.1913 0.1645 0.131 Uiso 1 1 calc R . . H21R H 0.6908 0.1034 0.3153 0.131 Uiso 1 1 calc R . . C217 C 0.62552(12) 0.0277(4) 0.1982(5) 0.1005(13) Uani 1 1 d . . . H21S H 0.5989 0.0045 0.2110 0.151 Uiso 1 1 calc R . . H21T H 0.6420 -0.0426 0.2375 0.151 Uiso 1 1 calc R . . H21U H 0.6296 0.0424 0.0866 0.151 Uiso 1 1 calc R . . C218 C 0.39167(9) 0.2478(4) 0.0194(4) 0.0670(10) Uani 1 1 d . . . H21V H 0.3966 0.3252 -0.0445 0.080 Uiso 1 1 calc R . . H21W H 0.3836 0.1773 -0.0531 0.080 Uiso 1 1 calc R . . C219 C 0.36850(11) 0.3931(4) 0.2195(5) 0.0886(11) Uani 1 1 d . . . H21X H 0.3912 0.3799 0.2888 0.133 Uiso 1 1 calc R . . H21Y H 0.3468 0.4118 0.2832 0.133 Uiso 1 1 calc R . . H21Z H 0.3727 0.4657 0.1488 0.133 Uiso 1 1 calc R . . C220 C 0.32385(10) 0.2940(5) 0.0332(5) 0.0932(13) Uani 1 1 d . . . H22A H 0.3038 0.3153 0.1046 0.140 Uiso 1 1 calc R . . H22B H 0.3172 0.2140 -0.0231 0.140 Uiso 1 1 calc R . . H22C H 0.3264 0.3642 -0.0426 0.140 Uiso 1 1 calc R . . N31 N 0.86488(6) 0.1751(2) 1.0474(2) 0.0453(6) Uani 1 1 d . . . N32 N 0.78601(6) 0.1738(2) 0.9599(2) 0.0444(5) Uani 1 1 d . . . N33 N 0.97428(6) 0.2104(2) 0.8663(3) 0.0567(6) Uani 1 1 d . . . N34 N 0.70075(6) 0.3549(2) 0.6685(3) 0.0568(6) Uani 1 1 d . . . C31 C 0.86969(7) 0.2464(2) 0.9027(3) 0.0398(6) Uani 1 1 d . . . C32 C 0.90614(8) 0.2854(3) 0.8653(3) 0.0471(7) Uani 1 1 d . . . C33 C 0.91131(8) 0.3624(3) 0.7276(3) 0.0543(7) Uani 1 1 d . . . H33A H 0.9358 0.3948 0.7079 0.065 Uiso 1 1 calc R . . C34 C 0.88107(8) 0.3899(3) 0.6236(3) 0.0525(7) Uani 1 1 d . . . H34A H 0.8852 0.4396 0.5325 0.063 Uiso 1 1 calc R . . C35 C 0.84364(8) 0.3449(2) 0.6506(3) 0.0432(6) Uani 1 1 d . . . C36 C 0.81323(8) 0.3688(3) 0.5353(3) 0.0542(8) Uani 1 1 d . . . H36A H 0.8186 0.4118 0.4405 0.065 Uiso 1 1 calc R . . C37 C 0.77634(8) 0.3308(3) 0.5587(3) 0.0547(8) Uani 1 1 d . . . H37A H 0.7570 0.3449 0.4790 0.066 Uiso 1 1 calc R . . C38 C 0.76741(8) 0.2707(3) 0.7022(3) 0.0454(6) Uani 1 1 d . . . C39 C 0.79639(8) 0.2400(3) 0.8190(3) 0.0394(6) Uani 1 1 d . . . C310 C 0.83626(8) 0.2752(2) 0.7949(3) 0.0371(6) Uani 1 1 d . . . C311 C 0.86149(9) 0.0351(3) 1.0421(4) 0.0646(8) Uani 1 1 d . . . H31A H 0.8507 0.0088 0.9387 0.097 Uiso 1 1 calc R . . H31B H 0.8449 0.0062 1.1240 0.097 Uiso 1 1 calc R . . H31C H 0.8866 -0.0038 1.0599 0.097 Uiso 1 1 calc R . . C312 C 0.87845(9) 0.2294(3) 1.2008(3) 0.0631(8) Uani 1 1 d . . . H31D H 0.8594 0.2147 1.2785 0.095 Uiso 1 1 calc R . . H31E H 0.8827 0.3223 1.1897 0.095 Uiso 1 1 calc R . . H31F H 0.9022 0.1873 1.2358 0.095 Uiso 1 1 calc R . . C313 C 0.76547(9) 0.0494(3) 0.9522(4) 0.0650(8) Uani 1 1 d . . . H31G H 0.7655 0.0152 0.8449 0.097 Uiso 1 1 calc R . . H31H H 0.7393 0.0627 0.9815 0.097 Uiso 1 1 calc R . . H31I H 0.7780 -0.0120 1.0251 0.097 Uiso 1 1 calc R . . C314 C 0.78235(8) 0.2485(3) 1.1047(3) 0.0622(8) Uani 1 1 d . . . H31J H 0.7995 0.3228 1.1046 0.093 Uiso 1 1 calc R . . H31K H 0.7889 0.1939 1.1960 0.093 Uiso 1 1 calc R . . H31L H 0.7562 0.2788 1.1103 0.093 Uiso 1 1 calc R . . C315 C 0.94201(8) 0.2428(3) 0.9638(3) 0.0563(8) Uani 1 1 d . . . H31M H 0.9498 0.3131 1.0373 0.068 Uiso 1 1 calc R . . H31N H 0.9357 0.1665 1.0274 0.068 Uiso 1 1 calc R . . C316 C 0.96540(10) 0.0989(4) 0.7645(4) 0.0849(10) Uani 1 1 d . . . H31O H 0.9423 0.1164 0.6995 0.127 Uiso 1 1 calc R . . H31P H 0.9615 0.0226 0.8297 0.127 Uiso 1 1 calc R . . H31Q H 0.9865 0.0832 0.6964 0.127 Uiso 1 1 calc R . . C317 C 1.00859(9) 0.1852(4) 0.9692(4) 0.0764(10) Uani 1 1 d . . . H31R H 1.0305 0.1733 0.9043 0.115 Uiso 1 1 calc R . . H31S H 1.0048 0.1070 1.0311 0.115 Uiso 1 1 calc R . . H31T H 1.0132 0.2585 1.0402 0.115 Uiso 1 1 calc R . . C318 C 0.72513(9) 0.2475(3) 0.7288(4) 0.0554(8) Uani 1 1 d . . . H31U H 0.7170 0.1665 0.6756 0.066 Uiso 1 1 calc R . . H31V H 0.7217 0.2367 0.8429 0.066 Uiso 1 1 calc R . . C319 C 0.70871(11) 0.4740(3) 0.7599(5) 0.0974(12) Uani 1 1 d . . . H31W H 0.6928 0.5442 0.7168 0.146 Uiso 1 1 calc R . . H31X H 0.7355 0.4972 0.7532 0.146 Uiso 1 1 calc R . . H31Y H 0.7032 0.4595 0.8701 0.146 Uiso 1 1 calc R . . C320 C 0.66034(10) 0.3224(4) 0.6764(5) 0.0811(11) Uani 1 1 d . . . H32A H 0.6449 0.3965 0.6414 0.122 Uiso 1 1 calc R . . H32B H 0.6549 0.3008 0.7851 0.122 Uiso 1 1 calc R . . H32C H 0.6543 0.2483 0.6081 0.122 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 N11 0.0590(15) 0.0500(15) 0.0411(13) 0.0029(12) -0.0032(11) 0.0004(12) N12 0.0547(14) 0.0492(15) 0.0387(13) 0.0037(11) 0.0050(10) -0.0050(11) N13 0.0489(13) 0.0574(15) 0.0524(13) -0.0042(12) -0.0033(10) 0.0041(11) N14 0.0463(14) 0.0840(18) 0.0641(15) -0.0071(14) 0.0049(12) -0.0055(12) C11 0.0542(17) 0.0458(16) 0.0317(14) -0.0012(13) 0.0067(12) 0.0016(13) C12 0.0539(18) 0.0598(19) 0.0451(16) -0.0013(14) 0.0051(13) 0.0003(14) C13 0.0560(19) 0.068(2) 0.0625(19) 0.0030(17) 0.0138(16) -0.0088(16) C14 0.066(2) 0.062(2) 0.0497(16) 0.0115(15) 0.0102(15) 0.0008(15) C15 0.0569(17) 0.0460(15) 0.0355(14) 0.0026(12) 0.0096(13) 0.0063(13) C16 0.066(2) 0.057(2) 0.0423(16) 0.0079(15) 0.0021(14) 0.0075(15) C17 0.0566(19) 0.0656(19) 0.0431(16) 0.0046(14) -0.0048(13) 0.0098(14) C18 0.0520(17) 0.0459(17) 0.0409(15) -0.0016(13) 0.0021(13) -0.0011(13) C19 0.0516(17) 0.0391(15) 0.0323(13) -0.0005(12) 0.0053(12) 0.0050(12) C110 0.0488(15) 0.0363(17) 0.0358(15) -0.0055(12) 0.0044(12) 0.0053(12) C111 0.094(2) 0.063(2) 0.064(2) 0.0107(17) -0.0069(17) 0.0153(18) C112 0.078(2) 0.093(2) 0.0418(16) 0.0000(17) -0.0028(14) -0.0034(18) C113 0.077(2) 0.077(2) 0.0456(15) -0.0036(16) 0.0169(14) 0.0017(16) C114 0.077(2) 0.0521(19) 0.072(2) 0.0133(16) 0.0068(16) -0.0037(16) C115 0.0466(17) 0.083(3) 0.0515(17) -0.0039(16) 0.0048(14) 0.0024(16) C116 0.072(2) 0.106(3) 0.097(3) -0.030(2) 0.0020(19) 0.004(2) C117 0.049(2) 0.131(4) 0.084(2) -0.008(2) -0.0080(19) 0.010(2) C118 0.0516(18) 0.066(2) 0.0542(17) 0.0031(16) 0.0033(14) -0.0050(15) C119 0.085(2) 0.068(2) 0.093(3) -0.0183(19) 0.0020(19) 0.0112(18) C120 0.050(2) 0.102(3) 0.085(2) -0.004(2) 0.0063(17) 0.0011(18) N21 0.0560(15) 0.0499(16) 0.0377(14) 0.0036(12) 0.0075(11) -0.0027(12) N22 0.0624(16) 0.0502(17) 0.0361(14) 0.0032(12) -0.0014(12) 0.0056(13) N23 0.0551(17) 0.0550(17) 0.0775(18) 0.0001(15) 0.0044(13) 0.0027(13) N24 0.0419(15) 0.088(2) 0.0619(16) -0.0063(15) 0.0000(12) -0.0047(13) C21 0.0486(17) 0.0366(17) 0.0373(14) -0.0017(14) 0.0049(13) 0.0007(13) C22 0.0582(19) 0.0470(18) 0.0425(16) 0.0050(14) 0.0022(15) 0.0069(15) C23 0.063(2) 0.069(2) 0.047(2) 0.0079(17) -0.0084(16) 0.0037(17) C24 0.068(2) 0.061(2) 0.0367(17) 0.0153(15) 0.0107(16) 0.0100(16) C25 0.0499(18) 0.0490(18) 0.0426(17) -0.0009(14) 0.0046(14) 0.0022(14) C26 0.069(2) 0.058(2) 0.0418(16) 0.0139(15) 0.0158(16) 0.0039(16) C27 0.0509(19) 0.072(2) 0.058(2) 0.0030(18) 0.0110(16) -0.0092(17) C28 0.0467(18) 0.059(2) 0.0436(17) -0.0022(15) 0.0026(14) 0.0024(15) C29 0.0486(17) 0.0405(18) 0.0398(16) -0.0034(15) 0.0053(13) 0.0046(14) C210 0.0539(18) 0.0370(14) 0.0331(15) 0.0005(13) 0.0081(13) 0.0077(14) C211 0.079(2) 0.057(2) 0.070(2) 0.0099(18) 0.0103(18) -0.0138(18) C212 0.077(2) 0.089(3) 0.0447(16) -0.0103(19) 0.0183(15) -0.0012(18) C213 0.093(3) 0.052(2) 0.072(2) 0.0147(18) -0.0009(18) 0.0085(19) C214 0.072(2) 0.087(3) 0.0417(17) 0.0029(17) -0.0023(15) -0.0041(18) C215 0.0517(19) 0.053(2) 0.0553(18) 0.0080(16) -0.0029(15) -0.0008(16) C216 0.059(2) 0.091(3) 0.111(3) 0.015(2) 0.001(2) 0.011(2) C217 0.104(3) 0.072(3) 0.128(4) -0.033(3) 0.034(3) -0.006(2) C218 0.063(2) 0.088(3) 0.0495(18) -0.0043(18) 0.0006(16) -0.0021(19) C219 0.086(3) 0.079(3) 0.100(3) -0.020(2) 0.001(2) 0.009(2) C220 0.055(2) 0.135(4) 0.088(3) 0.002(3) -0.0080(19) -0.006(2) N31 0.0514(14) 0.0483(15) 0.0364(12) 0.0055(11) 0.0031(10) -0.0048(11) N32 0.0525(14) 0.0432(13) 0.0377(12) 0.0028(11) 0.0059(10) -0.0080(11) N33 0.0492(14) 0.0557(15) 0.0655(15) -0.0034(12) 0.0060(12) 0.0004(11) N34 0.0523(14) 0.0517(15) 0.0663(16) 0.0017(13) -0.0001(12) 0.0064(12) C31 0.0492(17) 0.0376(15) 0.0327(13) -0.0026(12) 0.0036(12) 0.0048(12) C32 0.0497(17) 0.0453(18) 0.0468(16) -0.0050(13) 0.0084(13) 0.0007(13) C33 0.0535(18) 0.0562(18) 0.0544(17) 0.0043(14) 0.0154(14) -0.0045(14) C34 0.063(2) 0.0466(18) 0.0489(17) 0.0087(14) 0.0170(15) -0.0029(15) C35 0.0551(16) 0.0395(15) 0.0355(14) 0.0016(12) 0.0090(12) 0.0099(13) C36 0.068(2) 0.058(2) 0.0367(16) 0.0132(14) 0.0082(14) 0.0142(15) C37 0.0487(17) 0.072(2) 0.0432(17) 0.0083(15) -0.0022(13) 0.0150(15) C38 0.0486(16) 0.0453(16) 0.0422(15) -0.0013(13) 0.0024(13) 0.0032(13) C39 0.0554(17) 0.0328(14) 0.0304(13) -0.0021(12) 0.0043(12) 0.0070(12) C310 0.0465(15) 0.0309(15) 0.0347(14) -0.0035(12) 0.0087(11) -0.0006(12) C311 0.078(2) 0.0531(19) 0.0625(18) 0.0140(15) -0.0020(15) 0.0122(16) C312 0.0739(19) 0.078(2) 0.0381(14) -0.0037(15) 0.0060(13) -0.0031(16) C313 0.074(2) 0.054(2) 0.0667(19) 0.0122(16) 0.0019(16) -0.0107(16) C314 0.0631(18) 0.079(2) 0.0461(15) -0.0057(16) 0.0154(13) -0.0035(15) C315 0.0456(17) 0.068(2) 0.0555(18) -0.0016(16) 0.0036(14) 0.0047(14) C316 0.081(2) 0.085(3) 0.089(2) -0.026(2) 0.0121(19) 0.0078(19) C317 0.0427(18) 0.091(3) 0.096(3) 0.009(2) 0.0037(17) 0.0043(17) C318 0.0525(17) 0.054(2) 0.0586(19) 0.0027(16) -0.0059(14) -0.0011(15) C319 0.101(3) 0.062(2) 0.130(3) -0.021(2) 0.019(2) 0.006(2) C320 0.063(2) 0.082(3) 0.098(3) 0.012(2) -0.0007(19) 0.0039(19) _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 N11 C11 1.423(3) . ? N11 C111 1.436(4) . ? N11 C112 1.443(3) . ? N12 C19 1.422(3) . ? N12 C113 1.433(3) . ? N12 C114 1.445(3) . ? N13 C118 1.444(4) . ? N13 C119 1.449(4) . ? N13 C120 1.461(4) . ? N14 C117 1.439(4) . ? N14 C116 1.450(4) . ? N14 C115 1.478(4) . ? C11 C12 1.382(4) . ? C11 C110 1.455(4) . ? C12 C13 1.397(4) . ? C12 C115 1.508(4) . ? C13 C14 1.362(4) . ? C13 H13A 0.9300 . ? C14 C15 1.411(4) . ? C14 H14A 0.9300 . ? C15 C16 1.425(4) . ? C15 C110 1.425(3) . ? C16 C17 1.338(4) . ? C16 H16A 0.9300 . ? C17 C18 1.406(3) . ? C17 H17A 0.9300 . ? C18 C19 1.389(4) . ? C18 C118 1.526(4) . ? C19 C110 1.446(4) . ? C111 H11A 0.9600 . ? C111 H11B 0.9600 . ? C111 H11C 0.9600 . ? C112 H11D 0.9600 . ? C112 H11E 0.9600 . ? C112 H11F 0.9600 . ? C113 H11G 0.9600 . ? C113 H11H 0.9600 . ? C113 H11I 0.9600 . ? C114 H11J 0.9600 . ? C114 H11K 0.9600 . ? C114 H11L 0.9600 . ? C115 H11M 0.9700 . ? C115 H11N 0.9700 . ? C116 H11O 0.9600 . ? C116 H11P 0.9600 . ? C116 H11Q 0.9600 . ? C117 H11R 0.9600 . ? C117 H11S 0.9600 . ? C117 H11T 0.9600 . ? C118 H11U 0.9700 . ? C118 H11V 0.9700 . ? C119 H11W 0.9600 . ? C119 H11X 0.9600 . ? C119 H11Y 0.9600 . ? C120 H12A 0.9600 . ? C120 H12B 0.9600 . ? C120 H12C 0.9600 . ? N21 C21 1.410(3) . ? N21 C211 1.429(4) . ? N21 C212 1.440(3) . ? N22 C29 1.406(3) . ? N22 C214 1.432(4) . ? N22 C213 1.448(4) . ? N23 C217 1.430(4) . ? N23 C215 1.446(4) . ? N23 C216 1.456(4) . ? N24 C219 1.435(4) . ? N24 C218 1.456(4) . ? N24 C220 1.473(4) . ? C21 C22 1.393(4) . ? C21 C210 1.453(4) . ? C22 C23 1.409(4) . ? C22 C215 1.518(4) . ? C23 C24 1.346(4) . ? C23 H23A 0.9300 . ? C24 C25 1.401(4) . ? C24 H24A 0.9300 . ? C25 C26 1.415(4) . ? C25 C210 1.434(4) . ? C26 C27 1.337(4) . ? C26 H26A 0.9300 . ? C27 C28 1.406(4) . ? C27 H27A 0.9300 . ? C28 C29 1.396(4) . ? C28 C218 1.531(4) . ? C29 C210 1.456(3) . ? C211 H21B 0.9600 . ? C211 H21C 0.9600 . ? C211 H21D 0.9600 . ? C212 H21E 0.9600 . ? C212 H21F 0.9600 . ? C212 H21G 0.9600 . ? C213 H21H 0.9600 . ? C213 H21I 0.9600 . ? C213 H21J 0.9600 . ? C214 H21K 0.9600 . ? C214 H21L 0.9600 . ? C214 H21M 0.9600 . ? C215 H21N 0.9700 . ? C215 H21O 0.9700 . ? C216 H21P 0.9600 . ? C216 H21Q 0.9600 . ? C216 H21R 0.9600 . ? C217 H21S 0.9600 . ? C217 H21T 0.9600 . ? C217 H21U 0.9600 . ? C218 H21V 0.9700 . ? C218 H21W 0.9700 . ? C219 H21X 0.9600 . ? C219 H21Y 0.9600 . ? C219 H21Z 0.9600 . ? C220 H22A 0.9600 . ? C220 H22B 0.9600 . ? C220 H22C 0.9600 . ? N31 C31 1.424(3) . ? N31 C311 1.428(3) . ? N31 C312 1.449(3) . ? N32 C39 1.416(3) . ? N32 C314 1.437(3) . ? N32 C313 1.449(3) . ? N33 C316 1.440(4) . ? N33 C315 1.451(3) . ? N33 C317 1.452(4) . ? N34 C320 1.441(4) . ? N34 C319 1.449(4) . ? N34 C318 1.453(4) . ? C31 C32 1.372(4) . ? C31 C310 1.458(3) . ? C32 C33 1.408(4) . ? C32 C315 1.516(4) . ? C33 C34 1.353(4) . ? C33 H33A 0.9300 . ? C34 C35 1.402(4) . ? C34 H34A 0.9300 . ? C35 C36 1.410(4) . ? C35 C310 1.430(3) . ? C36 C37 1.356(4) . ? C36 H36A 0.9300 . ? C37 C38 1.392(3) . ? C37 H37A 0.9300 . ? C38 C39 1.397(4) . ? C38 C318 1.509(4) . ? C39 C310 1.448(4) . ? C311 H31A 0.9600 . ? C311 H31B 0.9600 . ? C311 H31C 0.9600 . ? C312 H31D 0.9600 . ? C312 H31E 0.9600 . ? C312 H31F 0.9600 . ? C313 H31G 0.9600 . ? C313 H31H 0.9600 . ? C313 H31I 0.9600 . ? C314 H31J 0.9600 . ? C314 H31K 0.9600 . ? C314 H31L 0.9600 . ? C315 H31M 0.9700 . ? C315 H31N 0.9700 . ? C316 H31O 0.9600 . ? C316 H31P 0.9600 . ? C316 H31Q 0.9600 . ? C317 H31R 0.9600 . ? C317 H31S 0.9600 . ? C317 H31T 0.9600 . ? C318 H31U 0.9700 . ? C318 H31V 0.9700 . ? C319 H31W 0.9600 . ? C319 H31X 0.9600 . ? C319 H31Y 0.9600 . ? C320 H32A 0.9600 . ? C320 H32B 0.9600 . ? C320 H32C 0.9600 . ? 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 N11 C111 117.9(2) . . ? C11 N11 C112 121.4(2) . . ? C111 N11 C112 116.0(2) . . ? C19 N12 C113 118.5(2) . . ? C19 N12 C114 120.6(2) . . ? C113 N12 C114 117.3(2) . . ? C118 N13 C119 111.5(2) . . ? C118 N13 C120 109.3(2) . . ? C119 N13 C120 109.0(3) . . ? C117 N14 C116 110.3(3) . . ? C117 N14 C115 109.9(2) . . ? C116 N14 C115 110.9(2) . . ? C12 C11 N11 119.7(2) . . ? C12 C11 C110 120.2(2) . . ? N11 C11 C110 120.1(2) . . ? C11 C12 C13 120.9(3) . . ? C11 C12 C115 121.3(3) . . ? C13 C12 C115 117.7(3) . . ? C14 C13 C12 120.9(3) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 C15 120.0(3) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C14 C15 C16 118.5(3) . . ? C14 C15 C110 121.2(3) . . ? C16 C15 C110 120.3(2) . . ? C17 C16 C15 120.9(3) . . ? C17 C16 H16A 119.5 . . ? C15 C16 H16A 119.5 . . ? C16 C17 C18 120.8(3) . . ? C16 C17 H17A 119.6 . . ? C18 C17 H17A 119.6 . . ? C19 C18 C17 120.6(3) . . ? C19 C18 C118 121.4(2) . . ? C17 C18 C118 118.0(2) . . ? C18 C19 N12 118.8(2) . . ? C18 C19 C110 120.2(2) . . ? N12 C19 C110 121.0(2) . . ? C15 C110 C19 117.0(2) . . ? C15 C110 C11 116.4(2) . . ? C19 C110 C11 126.6(2) . . ? N11 C111 H11A 109.5 . . ? N11 C111 H11B 109.5 . . ? H11A C111 H11B 109.5 . . ? N11 C111 H11C 109.5 . . ? H11A C111 H11C 109.5 . . ? H11B C111 H11C 109.5 . . ? N11 C112 H11D 109.5 . . ? N11 C112 H11E 109.5 . . ? H11D C112 H11E 109.5 . . ? N11 C112 H11F 109.5 . . ? H11D C112 H11F 109.5 . . ? H11E C112 H11F 109.5 . . ? N12 C113 H11G 109.5 . . ? N12 C113 H11H 109.5 . . ? H11G C113 H11H 109.5 . . ? N12 C113 H11I 109.5 . . ? H11G C113 H11I 109.5 . . ? H11H C113 H11I 109.5 . . ? N12 C114 H11J 109.5 . . ? N12 C114 H11K 109.5 . . ? H11J C114 H11K 109.5 . . ? N12 C114 H11L 109.5 . . ? H11J C114 H11L 109.5 . . ? H11K C114 H11L 109.5 . . ? N14 C115 C12 112.7(2) . . ? N14 C115 H11M 109.1 . . ? C12 C115 H11M 109.1 . . ? N14 C115 H11N 109.1 . . ? C12 C115 H11N 109.1 . . ? H11M C115 H11N 107.8 . . ? N14 C116 H11O 109.5 . . ? N14 C116 H11P 109.5 . . ? H11O C116 H11P 109.5 . . ? N14 C116 H11Q 109.5 . . ? H11O C116 H11Q 109.5 . . ? H11P C116 H11Q 109.5 . . ? N14 C117 H11R 109.5 . . ? N14 C117 H11S 109.5 . . ? H11R C117 H11S 109.5 . . ? N14 C117 H11T 109.5 . . ? H11R C117 H11T 109.5 . . ? H11S C117 H11T 109.5 . . ? N13 C118 C18 113.2(2) . . ? N13 C118 H11U 108.9 . . ? C18 C118 H11U 108.9 . . ? N13 C118 H11V 108.9 . . ? C18 C118 H11V 108.9 . . ? H11U C118 H11V 107.7 . . ? N13 C119 H11W 109.5 . . ? N13 C119 H11X 109.5 . . ? H11W C119 H11X 109.5 . . ? N13 C119 H11Y 109.5 . . ? H11W C119 H11Y 109.5 . . ? H11X C119 H11Y 109.5 . . ? N13 C120 H12A 109.5 . . ? N13 C120 H12B 109.5 . . ? H12A C120 H12B 109.5 . . ? N13 C120 H12C 109.5 . . ? H12A C120 H12C 109.5 . . ? H12B C120 H12C 109.5 . . ? C21 N21 C211 120.8(2) . . ? C21 N21 C212 119.3(2) . . ? C211 N21 C212 115.5(2) . . ? C29 N22 C214 120.9(2) . . ? C29 N22 C213 117.8(2) . . ? C214 N22 C213 116.8(3) . . ? C217 N23 C215 110.3(3) . . ? C217 N23 C216 109.4(3) . . ? C215 N23 C216 110.7(3) . . ? C219 N24 C218 111.9(3) . . ? C219 N24 C220 108.5(3) . . ? C218 N24 C220 110.1(3) . . ? C22 C21 N21 119.9(2) . . ? C22 C21 C210 119.7(3) . . ? N21 C21 C210 120.4(2) . . ? C21 C22 C23 120.1(3) . . ? C21 C22 C215 122.3(3) . . ? C23 C22 C215 117.6(3) . . ? C24 C23 C22 121.4(3) . . ? C24 C23 H23A 119.3 . . ? C22 C23 H23A 119.3 . . ? C23 C24 C25 120.5(3) . . ? C23 C24 H24A 119.7 . . ? C25 C24 H24A 119.7 . . ? C24 C25 C26 118.8(3) . . ? C24 C25 C210 120.9(3) . . ? C26 C25 C210 120.2(3) . . ? C27 C26 C25 121.3(3) . . ? C27 C26 H26A 119.3 . . ? C25 C26 H26A 119.3 . . ? C26 C27 C28 120.6(3) . . ? C26 C27 H27A 119.7 . . ? C28 C27 H27A 119.7 . . ? C29 C28 C27 121.3(3) . . ? C29 C28 C218 121.3(3) . . ? C27 C28 C218 117.4(3) . . ? C28 C29 N22 119.5(3) . . ? C28 C29 C210 119.0(2) . . ? N22 C29 C210 121.5(2) . . ? C25 C210 C21 116.8(2) . . ? C25 C210 C29 117.3(2) . . ? C21 C210 C29 125.9(2) . . ? N21 C211 H21B 109.5 . . ? N21 C211 H21C 109.5 . . ? H21B C211 H21C 109.5 . . ? N21 C211 H21D 109.5 . . ? H21B C211 H21D 109.5 . . ? H21C C211 H21D 109.5 . . ? N21 C212 H21E 109.5 . . ? N21 C212 H21F 109.5 . . ? H21E C212 H21F 109.5 . . ? N21 C212 H21G 109.5 . . ? H21E C212 H21G 109.5 . . ? H21F C212 H21G 109.5 . . ? N22 C213 H21H 109.5 . . ? N22 C213 H21I 109.5 . . ? H21H C213 H21I 109.5 . . ? N22 C213 H21J 109.5 . . ? H21H C213 H21J 109.5 . . ? H21I C213 H21J 109.5 . . ? N22 C214 H21K 109.5 . . ? N22 C214 H21L 109.5 . . ? H21K C214 H21L 109.5 . . ? N22 C214 H21M 109.5 . . ? H21K C214 H21M 109.5 . . ? H21L C214 H21M 109.5 . . ? N23 C215 C22 111.9(3) . . ? N23 C215 H21N 109.2 . . ? C22 C215 H21N 109.2 . . ? N23 C215 H21O 109.2 . . ? C22 C215 H21O 109.2 . . ? H21N C215 H21O 107.9 . . ? N23 C216 H21P 109.5 . . ? N23 C216 H21Q 109.5 . . ? H21P C216 H21Q 109.5 . . ? N23 C216 H21R 109.5 . . ? H21P C216 H21R 109.5 . . ? H21Q C216 H21R 109.5 . . ? N23 C217 H21S 109.5 . . ? N23 C217 H21T 109.5 . . ? H21S C217 H21T 109.5 . . ? N23 C217 H21U 109.5 . . ? H21S C217 H21U 109.5 . . ? H21T C217 H21U 109.5 . . ? N24 C218 C28 111.3(2) . . ? N24 C218 H21V 109.4 . . ? C28 C218 H21V 109.4 . . ? N24 C218 H21W 109.4 . . ? C28 C218 H21W 109.4 . . ? H21V C218 H21W 108.0 . . ? N24 C219 H21X 109.5 . . ? N24 C219 H21Y 109.5 . . ? H21X C219 H21Y 109.5 . . ? N24 C219 H21Z 109.5 . . ? H21X C219 H21Z 109.5 . . ? H21Y C219 H21Z 109.5 . . ? N24 C220 H22A 109.5 . . ? N24 C220 H22B 109.5 . . ? H22A C220 H22B 109.5 . . ? N24 C220 H22C 109.5 . . ? H22A C220 H22C 109.5 . . ? H22B C220 H22C 109.5 . . ? C31 N31 C311 119.5(2) . . ? C31 N31 C312 120.5(2) . . ? C311 N31 C312 115.4(2) . . ? C39 N32 C314 118.9(2) . . ? C39 N32 C313 121.4(2) . . ? C314 N32 C313 115.7(2) . . ? C316 N33 C315 111.2(2) . . ? C316 N33 C317 110.7(3) . . ? C315 N33 C317 109.7(2) . . ? C320 N34 C319 109.0(3) . . ? C320 N34 C318 111.1(3) . . ? C319 N34 C318 110.7(2) . . ? C32 C31 N31 119.2(2) . . ? C32 C31 C310 120.7(2) . . ? N31 C31 C310 120.1(2) . . ? C31 C32 C33 120.1(3) . . ? C31 C32 C315 122.0(3) . . ? C33 C32 C315 117.8(2) . . ? C34 C33 C32 120.7(3) . . ? C34 C33 H33A 119.6 . . ? C32 C33 H33A 119.6 . . ? C33 C34 C35 121.3(3) . . ? C33 C34 H34A 119.3 . . ? C35 C34 H34A 119.3 . . ? C34 C35 C36 119.8(3) . . ? C34 C35 C310 120.1(2) . . ? C36 C35 C310 120.0(3) . . ? C37 C36 C35 121.8(3) . . ? C37 C36 H36A 119.1 . . ? C35 C36 H36A 119.1 . . ? C36 C37 C38 120.0(3) . . ? C36 C37 H37A 120.0 . . ? C38 C37 H37A 120.0 . . ? C37 C38 C39 121.0(3) . . ? C37 C38 C318 117.0(2) . . ? C39 C38 C318 122.0(2) . . ? C38 C39 N32 118.8(2) . . ? C38 C39 C310 120.2(2) . . ? N32 C39 C310 121.0(2) . . ? C35 C310 C39 116.8(2) . . ? C35 C310 C31 116.7(2) . . ? C39 C310 C31 126.6(2) . . ? N31 C311 H31A 109.5 . . ? N31 C311 H31B 109.5 . . ? H31A C311 H31B 109.5 . . ? N31 C311 H31C 109.5 . . ? H31A C311 H31C 109.5 . . ? H31B C311 H31C 109.5 . . ? N31 C312 H31D 109.5 . . ? N31 C312 H31E 109.5 . . ? H31D C312 H31E 109.5 . . ? N31 C312 H31F 109.5 . . ? H31D C312 H31F 109.5 . . ? H31E C312 H31F 109.5 . . ? N32 C313 H31G 109.5 . . ? N32 C313 H31H 109.5 . . ? H31G C313 H31H 109.5 . . ? N32 C313 H31I 109.5 . . ? H31G C313 H31I 109.5 . . ? H31H C313 H31I 109.5 . . ? N32 C314 H31J 109.5 . . ? N32 C314 H31K 109.5 . . ? H31J C314 H31K 109.5 . . ? N32 C314 H31L 109.5 . . ? H31J C314 H31L 109.5 . . ? H31K C314 H31L 109.5 . . ? N33 C315 C32 113.1(2) . . ? N33 C315 H31M 109.0 . . ? C32 C315 H31M 109.0 . . ? N33 C315 H31N 109.0 . . ? C32 C315 H31N 109.0 . . ? H31M C315 H31N 107.8 . . ? N33 C316 H31O 109.5 . . ? N33 C316 H31P 109.5 . . ? H31O C316 H31P 109.5 . . ? N33 C316 H31Q 109.5 . . ? H31O C316 H31Q 109.5 . . ? H31P C316 H31Q 109.5 . . ? N33 C317 H31R 109.5 . . ? N33 C317 H31S 109.5 . . ? H31R C317 H31S 109.5 . . ? N33 C317 H31T 109.5 . . ? H31R C317 H31T 109.5 . . ? H31S C317 H31T 109.5 . . ? N34 C318 C38 112.4(3) . . ? N34 C318 H31U 109.1 . . ? C38 C318 H31U 109.1 . . ? N34 C318 H31V 109.1 . . ? C38 C318 H31V 109.1 . . ? H31U C318 H31V 107.9 . . ? N34 C319 H31W 109.5 . . ? N34 C319 H31X 109.5 . . ? H31W C319 H31X 109.5 . . ? N34 C319 H31Y 109.5 . . ? H31W C319 H31Y 109.5 . . ? H31X C319 H31Y 109.5 . . ? N34 C320 H32A 109.5 . . ? N34 C320 H32B 109.5 . . ? H32A C320 H32B 109.5 . . ? N34 C320 H32C 109.5 . . ? H32A C320 H32C 109.5 . . ? H32B C320 H32C 109.5 . . ? 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 C111 N11 C11 C12 -100.1(3) . . . . ? C112 N11 C11 C12 54.6(4) . . . . ? C111 N11 C11 C110 79.8(3) . . . . ? C112 N11 C11 C110 -125.5(3) . . . . ? N11 C11 C12 C13 -176.6(2) . . . . ? C110 C11 C12 C13 3.5(4) . . . . ? N11 C11 C12 C115 6.2(4) . . . . ? C110 C11 C12 C115 -173.8(3) . . . . ? C11 C12 C13 C14 -5.0(5) . . . . ? C115 C12 C13 C14 172.3(3) . . . . ? C12 C13 C14 C15 1.1(5) . . . . ? C13 C14 C15 C16 -177.7(3) . . . . ? C13 C14 C15 C110 4.4(4) . . . . ? C14 C15 C16 C17 -176.8(3) . . . . ? C110 C15 C16 C17 1.2(4) . . . . ? C15 C16 C17 C18 3.6(4) . . . . ? C16 C17 C18 C19 -6.0(4) . . . . ? C16 C17 C18 C118 170.9(3) . . . . ? C17 C18 C19 N12 -177.0(2) . . . . ? C118 C18 C19 N12 6.2(4) . . . . ? C17 C18 C19 C110 3.5(4) . . . . ? C118 C18 C19 C110 -173.3(2) . . . . ? C113 N12 C19 C18 -100.7(3) . . . . ? C114 N12 C19 C18 57.1(3) . . . . ? C113 N12 C19 C110 78.8(3) . . . . ? C114 N12 C19 C110 -123.5(3) . . . . ? C14 C15 C110 C19 174.5(2) . . . . ? C16 C15 C110 C19 -3.4(4) . . . . ? C14 C15 C110 C11 -5.6(4) . . . . ? C16 C15 C110 C11 176.5(3) . . . . ? C18 C19 C110 C15 1.1(3) . . . . ? N12 C19 C110 C15 -178.4(2) . . . . ? C18 C19 C110 C11 -178.8(3) . . . . ? N12 C19 C110 C11 1.8(4) . . . . ? C12 C11 C110 C15 1.7(4) . . . . ? N11 C11 C110 C15 -178.2(2) . . . . ? C12 C11 C110 C19 -178.4(2) . . . . ? N11 C11 C110 C19 1.7(4) . . . . ? C117 N14 C115 C12 171.3(3) . . . . ? C116 N14 C115 C12 -66.5(4) . . . . ? C11 C12 C115 N14 140.7(3) . . . . ? C13 C12 C115 N14 -36.6(4) . . . . ? C119 N13 C118 C18 -66.8(3) . . . . ? C120 N13 C118 C18 172.6(2) . . . . ? C19 C18 C118 N13 145.4(2) . . . . ? C17 C18 C118 N13 -31.5(4) . . . . ? C211 N21 C21 C22 -55.1(4) . . . . ? C212 N21 C21 C22 100.4(3) . . . . ? C211 N21 C21 C210 126.6(3) . . . . ? C212 N21 C21 C210 -78.0(3) . . . . ? N21 C21 C22 C23 176.2(3) . . . . ? C210 C21 C22 C23 -5.4(4) . . . . ? N21 C21 C22 C215 -6.2(4) . . . . ? C210 C21 C22 C215 172.2(3) . . . . ? C21 C22 C23 C24 8.0(5) . . . . ? C215 C22 C23 C24 -169.8(3) . . . . ? C22 C23 C24 C25 -3.0(5) . . . . ? C23 C24 C25 C26 178.6(3) . . . . ? C23 C24 C25 C210 -4.4(5) . . . . ? C24 C25 C26 C27 176.0(3) . . . . ? C210 C25 C26 C27 -1.0(4) . . . . ? C25 C26 C27 C28 -4.6(5) . . . . ? C26 C27 C28 C29 7.4(5) . . . . ? C26 C27 C28 C218 -169.7(3) . . . . ? C27 C28 C29 N22 175.8(3) . . . . ? C218 C28 C29 N22 -7.2(4) . . . . ? C27 C28 C29 C210 -4.4(4) . . . . ? C218 C28 C29 C210 172.6(3) . . . . ? C214 N22 C29 C28 -54.7(4) . . . . ? C213 N22 C29 C28 100.8(3) . . . . ? C214 N22 C29 C210 125.5(3) . . . . ? C213 N22 C29 C210 -79.0(3) . . . . ? C24 C25 C210 C21 6.6(4) . . . . ? C26 C25 C210 C21 -176.5(3) . . . . ? C24 C25 C210 C29 -173.2(3) . . . . ? C26 C25 C210 C29 3.8(4) . . . . ? C22 C21 C210 C25 -1.6(4) . . . . ? N21 C21 C210 C25 176.7(2) . . . . ? C22 C21 C210 C29 178.1(3) . . . . ? N21 C21 C210 C29 -3.5(4) . . . . ? C28 C29 C210 C25 -1.0(4) . . . . ? N22 C29 C210 C25 178.8(3) . . . . ? C28 C29 C210 C21 179.2(3) . . . . ? N22 C29 C210 C21 -1.0(4) . . . . ? C217 N23 C215 C22 66.5(3) . . . . ? C216 N23 C215 C22 -172.3(3) . . . . ? C21 C22 C215 N23 -138.8(3) . . . . ? C23 C22 C215 N23 38.9(4) . . . . ? C219 N24 C218 C28 68.3(4) . . . . ? C220 N24 C218 C28 -171.0(3) . . . . ? C29 C28 C218 N24 -139.2(3) . . . . ? C27 C28 C218 N24 38.0(4) . . . . ? C311 N31 C31 C32 -98.7(3) . . . . ? C312 N31 C31 C32 56.3(3) . . . . ? C311 N31 C31 C310 80.2(3) . . . . ? C312 N31 C31 C310 -124.7(3) . . . . ? N31 C31 C32 C33 -176.3(2) . . . . ? C310 C31 C32 C33 4.7(4) . . . . ? N31 C31 C32 C315 6.6(4) . . . . ? C310 C31 C32 C315 -172.3(2) . . . . ? C31 C32 C33 C34 -5.5(4) . . . . ? C315 C32 C33 C34 171.7(3) . . . . ? C32 C33 C34 C35 1.1(4) . . . . ? C33 C34 C35 C36 -176.3(3) . . . . ? C33 C34 C35 C310 3.8(4) . . . . ? C34 C35 C36 C37 -177.8(3) . . . . ? C310 C35 C36 C37 2.0(4) . . . . ? C35 C36 C37 C38 2.4(5) . . . . ? C36 C37 C38 C39 -4.6(4) . . . . ? C36 C37 C38 C318 172.1(3) . . . . ? C37 C38 C39 N32 -177.3(2) . . . . ? C318 C38 C39 N32 6.1(4) . . . . ? C37 C38 C39 C310 2.5(4) . . . . ? C318 C38 C39 C310 -174.1(3) . . . . ? C314 N32 C39 C38 -100.8(3) . . . . ? C313 N32 C39 C38 55.8(3) . . . . ? C314 N32 C39 C310 79.4(3) . . . . ? C313 N32 C39 C310 -124.0(3) . . . . ? C34 C35 C310 C39 175.8(2) . . . . ? C36 C35 C310 C39 -4.0(3) . . . . ? C34 C35 C310 C31 -4.4(3) . . . . ? C36 C35 C310 C31 175.8(2) . . . . ? C38 C39 C310 C35 1.8(3) . . . . ? N32 C39 C310 C35 -178.4(2) . . . . ? C38 C39 C310 C31 -178.0(2) . . . . ? N32 C39 C310 C31 1.8(4) . . . . ? C32 C31 C310 C35 0.1(3) . . . . ? N31 C31 C310 C35 -178.8(2) . . . . ? C32 C31 C310 C39 179.9(2) . . . . ? N31 C31 C310 C39 1.0(4) . . . . ? C316 N33 C315 C32 -63.6(3) . . . . ? C317 N33 C315 C32 173.6(3) . . . . ? C31 C32 C315 N33 139.7(3) . . . . ? C33 C32 C315 N33 -37.4(4) . . . . ? C320 N34 C318 C38 172.5(3) . . . . ? C319 N34 C318 C38 -66.3(3) . . . . ? C37 C38 C318 N34 -37.9(4) . . . . ? C39 C38 C318 N34 138.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.156 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.027 _publ_section_references ; Bruker, Programs APEX II, version 2.0-1; SAINT, version 7.23A; SADABS, version 2004/1; XPREP, version 2005/2; SHELXTL, version 6.1. Bruker AXS Inc., Madison, WI, USA, 2005. G.M. Sheldrick, Programs SHELXS97 (crystal structure solution) and SHELXL97 (crystal structure refinement), University of Gottingen, Germany, 1997. ; #===END data_final _database_code_depnum_ccdc_archive 'CCDC 804543' #TrackingRef 't-Amino-Fig1-to-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H22 N5' _chemical_formula_sum 'C24 H22 N5' _chemical_formula_weight 380.47 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.247(4) _cell_length_b 11.520(4) _cell_length_c 34.634(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.208(7) _cell_angle_gamma 90.00 _cell_volume 3996(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 230 _cell_measurement_theta_min 3 _cell_measurement_theta_max 24 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.13 _exptl_absorpt_correction_T_max 0.44 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 "Bruker APEX II CCD area detector'" _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29279 _diffrn_reflns_av_R_equivalents 0.2366 _diffrn_reflns_av_sigmaI/netI 0.2106 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 24.00 _reflns_number_total 5974 _reflns_number_gt 2961 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0356P)^2^] 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 0.0276(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5974 _refine_ls_number_parameters 509 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1712 _refine_ls_R_factor_gt 0.0859 _refine_ls_wR_factor_ref 0.1612 _refine_ls_wR_factor_gt 0.1414 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 N1' N 0.8781(4) -0.3330(3) 0.06953(12) 0.0238(10) Uani 1 1 d . . . N1 N 1.2172(4) 0.3703(4) 0.20452(12) 0.0303(11) Uani 1 1 d . . . N2' N 0.7853(4) -0.0982(3) 0.04765(11) 0.0220(10) Uani 1 1 d . . . N2 N 1.3820(4) 0.3856(4) 0.28308(12) 0.0285(11) Uani 1 1 d . . . N3' N 1.3752(4) -0.6581(3) 0.09356(10) 0.0188(10) Uiso 1 1 d . . . N3 N 0.6595(4) 0.3643(3) 0.08868(11) 0.0202(10) Uani 1 1 d . . . N4' N 1.1566(4) -0.6836(3) 0.09269(11) 0.0214(10) Uani 1 1 d . . . N4 N 0.8770(4) 0.3400(3) 0.08723(11) 0.0216(10) Uani 1 1 d . . . N5' N 1.4546(4) -0.3543(4) 0.10840(12) 0.0320(11) Uani 1 1 d . . . N5 N 0.6394(4) 0.5000(4) 0.17938(13) 0.0317(11) Uani 1 1 d . . . C1 C 1.1562(5) 0.4615(4) 0.21903(14) 0.0243(13) Uani 1 1 d . . . C1' C 0.9708(5) -0.2663(4) 0.09604(14) 0.0206(12) Uani 1 1 d . . . C2' C 1.0947(4) -0.3204(4) 0.11271(14) 0.0203(12) Uani 1 1 d . . . C2 C 1.0250(5) 0.4933(4) 0.20065(14) 0.0217(12) Uani 1 1 d . . . C3' C 1.1788(5) -0.2651(4) 0.14608(14) 0.0239(12) Uani 1 1 d . . . H3'A H 1.2634 -0.2954 0.1560 0.029 Uiso 1 1 calc R . . C3 C 0.9697(5) 0.5987(4) 0.21005(14) 0.0275(13) Uani 1 1 d . . . H3A H 0.8803 0.6150 0.1997 0.033 Uiso 1 1 calc R . . C4 C 1.0462(5) 0.6768(5) 0.23419(14) 0.0298(13) Uani 1 1 d . . . H4A H 1.0126 0.7505 0.2371 0.036 Uiso 1 1 calc R . . C4' C 1.1392(4) -0.1717(4) 0.16329(15) 0.0234(12) Uani 1 1 d . . . H4'A H 1.1917 -0.1441 0.1867 0.028 Uiso 1 1 calc R . . C5' C 1.0168(5) -0.1130(4) 0.14629(14) 0.0207(12) Uani 1 1 d . . . C5 C 1.1756(5) 0.6475(4) 0.25482(14) 0.0244(12) Uani 1 1 d . . . C6' C 0.9749(5) -0.0154(4) 0.16417(15) 0.0251(13) Uani 1 1 d . . . H6'A H 1.0224 0.0078 0.1889 0.030 Uiso 1 1 calc R . . C6 C 1.2521(5) 0.7319(5) 0.27953(14) 0.0291(14) Uani 1 1 d . . . H6A H 1.2198 0.8070 0.2806 0.035 Uiso 1 1 calc R . . C7' C 0.8653(5) 0.0470(4) 0.14612(15) 0.0264(13) Uani 1 1 d . . . H7'A H 0.8330 0.1076 0.1592 0.032 Uiso 1 1 calc R . . C7 C 1.3747(5) 0.7015(5) 0.30193(15) 0.0361(15) Uani 1 1 d . . . H7A H 1.4282 0.7578 0.3168 0.043 Uiso 1 1 calc R . . C8' C 0.8035(5) 0.0171(4) 0.10771(15) 0.0224(12) Uani 1 1 d . . . H8'A H 0.7348 0.0644 0.0945 0.027 Uiso 1 1 calc R . . C8 C 1.4192(5) 0.5885(5) 0.30262(15) 0.0321(14) Uani 1 1 d . . . H8A H 1.5001 0.5693 0.3192 0.038 Uiso 1 1 calc R . . C9' C 0.8374(5) -0.0767(4) 0.08829(15) 0.0218(12) Uani 1 1 d . . . C9 C 1.3463(5) 0.5012(5) 0.27906(15) 0.0260(13) Uani 1 1 d . . . C10 C 1.2269(5) 0.5367(4) 0.25083(14) 0.0235(12) Uani 1 1 d . . . C10' C 0.9411(4) -0.1549(4) 0.10965(14) 0.0195(12) Uani 1 1 d . . . C11' C 0.7389(5) -0.3336(4) 0.07238(16) 0.0326(14) Uani 1 1 d . . . H11A H 0.7311 -0.3032 0.0976 0.049 Uiso 1 1 calc R . . H11B H 0.7055 -0.4116 0.0697 0.049 Uiso 1 1 calc R . . H11C H 0.6881 -0.2862 0.0518 0.049 Uiso 1 1 calc R . . C11 C 1.1661(6) 0.2528(4) 0.20023(16) 0.0380(15) Uani 1 1 d . . . H11D H 1.0758 0.2520 0.2039 0.057 Uiso 1 1 calc R . . H11E H 1.2203 0.2039 0.2197 0.057 Uiso 1 1 calc R . . H11F H 1.1682 0.2245 0.1743 0.057 Uiso 1 1 calc R . . C12' C 0.9016(5) -0.3766(4) 0.03257(14) 0.0300(13) Uani 1 1 d . . . H12A H 0.9954 -0.3729 0.0328 0.045 Uiso 1 1 calc R . . H12B H 0.8533 -0.3302 0.0112 0.045 Uiso 1 1 calc R . . H12C H 0.8719 -0.4557 0.0291 0.045 Uiso 1 1 calc R . . C12 C 1.3525(5) 0.3812(5) 0.19930(16) 0.0443(17) Uani 1 1 d . . . H12D H 1.3798 0.4610 0.2026 0.066 Uiso 1 1 calc R . . H12E H 1.3574 0.3556 0.1733 0.066 Uiso 1 1 calc R . . H12F H 1.4104 0.3344 0.2186 0.066 Uiso 1 1 calc R . . C13' C 0.8834(5) -0.0848(4) 0.02303(14) 0.0266(13) Uani 1 1 d . . . H13A H 0.9635 -0.1257 0.0348 0.040 Uiso 1 1 calc R . . H13B H 0.9032 -0.0039 0.0208 0.040 Uiso 1 1 calc R . . H13C H 0.8480 -0.1159 -0.0028 0.040 Uiso 1 1 calc R . . C13 C 1.2902(5) 0.3116(5) 0.29903(17) 0.0401(15) Uani 1 1 d . . . H13D H 1.1999 0.3302 0.2864 0.060 Uiso 1 1 calc R . . H13E H 1.3026 0.3242 0.3270 0.060 Uiso 1 1 calc R . . H13F H 1.3078 0.2317 0.2941 0.060 Uiso 1 1 calc R . . C14' C 0.6628(5) -0.0360(4) 0.03016(15) 0.0265(13) Uani 1 1 d . . . H14A H 0.5990 -0.0450 0.0467 0.040 Uiso 1 1 calc R . . H14B H 0.6264 -0.0670 0.0044 0.040 Uiso 1 1 calc R . . H14C H 0.6824 0.0449 0.0279 0.040 Uiso 1 1 calc R . . C14 C 1.5204(5) 0.3585(6) 0.30126(18) 0.0541(19) Uani 1 1 d . . . H14D H 1.5789 0.4076 0.2902 0.081 Uiso 1 1 calc R . . H14E H 1.5384 0.2787 0.2963 0.081 Uiso 1 1 calc R . . H14F H 1.5351 0.3714 0.3292 0.081 Uiso 1 1 calc R . . C15' C 1.1228(5) -0.4348(4) 0.10152(13) 0.0228(12) Uani 1 1 d . . . H15A H 1.0489 -0.4828 0.0939 0.027 Uiso 1 1 calc R . . C15 C 0.9606(5) 0.4315(4) 0.16589(14) 0.0246(13) Uani 1 1 d . . . H15B H 1.0177 0.3888 0.1537 0.030 Uiso 1 1 calc R . . C16' C 1.2420(4) -0.4837(4) 0.10040(14) 0.0210(12) Uani 1 1 d . . . C16 C 0.8289(5) 0.4252(4) 0.14779(14) 0.0214(12) Uiso 1 1 d . . . C17' C 1.3607(5) -0.4140(4) 0.10569(14) 0.0219(12) Uani 1 1 d . . . C17 C 0.7235(5) 0.4694(4) 0.16557(15) 0.0234(13) Uani 1 1 d . . . C18' C 1.2590(4) -0.6067(4) 0.09511(13) 0.0169(11) Uiso 1 1 d . . . C18 C 0.7895(4) 0.3741(4) 0.10861(14) 0.0215(12) Uani 1 1 d . . . C19 C 0.6653(4) 0.3230(4) 0.05132(14) 0.0182(11) Uani 1 1 d . . . C19' C 1.3459(4) -0.7760(4) 0.09102(13) 0.0190(12) Uani 1 1 d . . . C20 C 0.5652(5) 0.3017(4) 0.01780(14) 0.0290(13) Uani 1 1 d . . . H20A H 0.4753 0.3108 0.0182 0.035 Uiso 1 1 calc R . . C20' C 1.4290(5) -0.8711(4) 0.09000(13) 0.0232(12) Uani 1 1 d . . . H20B H 1.5190 -0.8609 0.0899 0.028 Uiso 1 1 calc R . . C21' C 1.3747(5) -0.9809(5) 0.08910(14) 0.0287(13) Uani 1 1 d . . . H21A H 1.4285 -1.0455 0.0882 0.034 Uiso 1 1 calc R . . C21 C 0.6056(5) 0.2667(4) -0.01595(15) 0.0266(13) Uani 1 1 d . . . H21B H 0.5422 0.2542 -0.0391 0.032 Uiso 1 1 calc R . . C22' C 1.2393(5) -0.9962(4) 0.08947(14) 0.0266(13) Uani 1 1 d . . . H22A H 1.2054 -1.0710 0.0897 0.032 Uiso 1 1 calc R . . C22 C 0.7407(5) 0.2498(4) -0.01566(15) 0.0263(13) Uani 1 1 d . . . H22B H 0.7654 0.2248 -0.0386 0.032 Uiso 1 1 calc R . . C23 C 0.8379(5) 0.2692(4) 0.01756(14) 0.0229(12) Uani 1 1 d . . . H23A H 0.9275 0.2572 0.0174 0.028 Uiso 1 1 calc R . . C23' C 1.1554(5) -0.9034(4) 0.08951(13) 0.0232(12) Uani 1 1 d . . . H23B H 1.0649 -0.9138 0.0887 0.028 Uiso 1 1 calc R . . C24 C 0.7994(5) 0.3066(4) 0.05107(14) 0.0193(12) Uani 1 1 d . . . C24' C 1.2112(5) -0.7932(4) 0.09073(13) 0.0194(12) 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 N1' 0.006(2) 0.027(3) 0.036(3) -0.005(2) 0.000(2) -0.0042(18) N1 0.011(2) 0.032(3) 0.049(3) -0.011(2) 0.009(2) 0.004(2) N2' 0.006(2) 0.033(3) 0.028(3) 0.002(2) 0.0060(19) 0.0078(18) N2 0.014(2) 0.022(3) 0.047(3) 0.001(2) 0.002(2) -0.001(2) N3 0.008(2) 0.026(2) 0.025(2) 0.003(2) 0.0020(19) -0.0058(18) N4' 0.016(2) 0.018(2) 0.030(3) -0.0008(19) 0.0065(19) -0.0042(18) N4 0.013(2) 0.020(2) 0.033(3) 0.0008(19) 0.006(2) 0.0019(18) N5' 0.018(2) 0.036(3) 0.042(3) 0.006(2) 0.004(2) -0.003(2) N5 0.018(2) 0.032(3) 0.047(3) 0.004(2) 0.008(2) 0.001(2) C1 0.013(3) 0.033(3) 0.028(3) 0.000(3) 0.008(2) 0.002(2) C1' 0.018(3) 0.019(3) 0.027(3) 0.003(2) 0.010(2) -0.002(2) C2' 0.012(3) 0.021(3) 0.029(3) 0.000(2) 0.006(2) 0.002(2) C2 0.014(3) 0.023(3) 0.029(3) -0.001(2) 0.007(2) -0.002(2) C3' 0.015(3) 0.023(3) 0.034(3) 0.007(3) 0.005(2) -0.005(2) C3 0.015(3) 0.029(3) 0.037(3) -0.002(3) 0.003(3) -0.010(2) C4 0.026(3) 0.030(3) 0.035(3) 0.000(3) 0.009(3) -0.004(3) C4' 0.006(2) 0.027(3) 0.038(3) 0.000(3) 0.005(2) -0.003(2) C5' 0.017(3) 0.019(3) 0.029(3) -0.006(2) 0.009(2) -0.003(2) C5 0.024(3) 0.019(3) 0.031(3) 0.000(2) 0.008(3) -0.008(2) C6' 0.016(3) 0.029(3) 0.031(3) -0.004(2) 0.007(2) -0.002(2) C6 0.021(3) 0.026(3) 0.042(4) -0.004(3) 0.010(3) -0.010(2) C7' 0.025(3) 0.023(3) 0.036(3) -0.004(3) 0.016(3) 0.008(2) C7 0.020(3) 0.045(4) 0.042(4) 0.001(3) 0.004(3) -0.005(3) C8' 0.014(3) 0.017(3) 0.038(3) 0.007(3) 0.010(2) 0.003(2) C8 0.013(3) 0.042(4) 0.039(3) 0.001(3) 0.001(2) -0.005(3) C9' 0.009(3) 0.026(3) 0.034(3) 0.003(3) 0.012(2) 0.005(2) C9 0.015(3) 0.032(3) 0.033(3) -0.001(3) 0.007(2) 0.001(2) C10 0.014(3) 0.028(3) 0.029(3) -0.005(2) 0.006(2) -0.001(2) C10' 0.008(2) 0.024(3) 0.029(3) 0.000(2) 0.011(2) 0.002(2) C11' 0.019(3) 0.021(3) 0.056(4) 0.004(3) 0.002(3) -0.003(2) C11 0.039(4) 0.032(4) 0.042(4) -0.008(3) 0.006(3) 0.012(3) C12' 0.037(3) 0.018(3) 0.033(3) 0.000(3) 0.005(3) -0.003(2) C12 0.010(3) 0.072(5) 0.051(4) -0.016(3) 0.005(3) 0.007(3) C13' 0.019(3) 0.031(3) 0.032(3) 0.005(3) 0.012(2) 0.004(2) C13 0.026(3) 0.037(4) 0.056(4) 0.003(3) 0.006(3) -0.004(3) C14' 0.015(3) 0.026(3) 0.038(3) 0.002(3) 0.004(2) 0.005(2) C14 0.008(3) 0.083(5) 0.064(4) -0.003(4) -0.008(3) 0.010(3) C15' 0.013(3) 0.027(3) 0.029(3) 0.007(2) 0.005(2) -0.005(2) C15 0.014(3) 0.030(3) 0.031(3) -0.002(3) 0.006(2) 0.003(2) C16' 0.008(3) 0.026(3) 0.027(3) 0.005(2) -0.001(2) -0.005(2) C17' 0.020(3) 0.019(3) 0.026(3) 0.002(2) 0.003(2) 0.006(2) C17 0.012(3) 0.018(3) 0.040(4) -0.003(2) 0.005(3) 0.004(2) C18 0.007(3) 0.021(3) 0.038(3) 0.004(2) 0.008(2) 0.002(2) C19 0.010(3) 0.015(3) 0.029(3) -0.001(2) 0.003(2) -0.001(2) C19' 0.010(3) 0.021(3) 0.027(3) 0.000(2) 0.007(2) 0.006(2) C20 0.017(3) 0.043(4) 0.024(3) 0.002(3) -0.002(3) 0.000(3) C20' 0.014(3) 0.021(3) 0.037(3) 0.002(2) 0.012(2) 0.004(2) C21' 0.026(3) 0.032(3) 0.029(3) 0.004(3) 0.007(3) 0.010(3) C21 0.026(3) 0.027(3) 0.024(3) -0.002(2) -0.003(2) -0.001(2) C22' 0.023(3) 0.029(3) 0.030(3) 0.002(3) 0.011(2) 0.006(2) C22 0.017(3) 0.034(3) 0.029(3) 0.001(3) 0.008(2) 0.004(2) C23 0.021(3) 0.020(3) 0.029(3) -0.004(2) 0.006(3) -0.010(2) C23' 0.022(3) 0.018(3) 0.032(3) 0.002(2) 0.010(2) 0.003(2) C24 0.026(3) 0.009(3) 0.021(3) 0.002(2) -0.001(2) -0.005(2) C24' 0.015(3) 0.017(3) 0.028(3) 0.004(2) 0.008(2) 0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1' C1' 1.402(6) . ? N1' C12' 1.442(6) . ? N1' C11' 1.450(6) . ? N1 C1 1.372(6) . ? N1 C12 1.441(6) . ? N1 C11 1.448(6) . ? N2' C9' 1.418(6) . ? N2' C13' 1.457(6) . ? N2' C14' 1.461(6) . ? N2 C9 1.379(6) . ? N2 C14 1.459(6) . ? N2 C13 1.462(6) . ? N3' C18' 1.340(6) . ? N3' C19' 1.390(6) . ? N3 C18 1.369(6) . ? N3 C19 1.392(6) . ? N4' C18' 1.362(6) . ? N4' C24' 1.388(6) . ? N4 C18 1.337(6) . ? N4 C24 1.388(6) . ? N5' C17' 1.171(6) . ? N5 C17 1.127(6) . ? C1 C2 1.409(6) . ? C1 C10 1.466(7) . ? C1' C2' 1.423(6) . ? C1' C10' 1.422(6) . ? C2' C15' 1.420(6) . ? C2' C3' 1.436(6) . ? C2 C3 1.407(7) . ? C2 C15 1.433(6) . ? C3' C4' 1.335(6) . ? C3' H3'A 0.9300 . ? C3 C4 1.359(6) . ? C3 H3A 0.9300 . ? C4 C5 1.408(7) . ? C4 H4A 0.9300 . ? C4' C5' 1.437(6) . ? C4' H4'A 0.9300 . ? C5' C6' 1.395(6) . ? C5' C10' 1.424(6) . ? C5 C10 1.399(7) . ? C5 C6 1.417(6) . ? C6' C7' 1.368(6) . ? C6' H6'A 0.9300 . ? C6 C7 1.375(7) . ? C6 H6A 0.9300 . ? C7' C8' 1.390(6) . ? C7' H7'A 0.9300 . ? C7 C8 1.377(7) . ? C7 H7A 0.9300 . ? C8' C9' 1.356(6) . ? C8' H8'A 0.9300 . ? C8 C9 1.407(7) . ? C8 H8A 0.9300 . ? C9' C10' 1.469(6) . ? C9 C10 1.454(7) . ? C11' H11A 0.9600 . ? C11' H11B 0.9600 . ? C11' H11C 0.9600 . ? C11 H11D 0.9600 . ? C11 H11E 0.9600 . ? C11 H11F 0.9600 . ? C12' H12A 0.9600 . ? C12' H12B 0.9600 . ? C12' H12C 0.9600 . ? C12 H12D 0.9600 . ? C12 H12E 0.9600 . ? C12 H12F 0.9600 . ? C13' H13A 0.9600 . ? C13' H13B 0.9600 . ? C13' H13C 0.9600 . ? C13 H13D 0.9600 . ? C13 H13E 0.9600 . ? C13 H13F 0.9600 . ? C14' H14A 0.9600 . ? C14' H14B 0.9600 . ? C14' H14C 0.9600 . ? C14 H14D 0.9600 . ? C14 H14E 0.9600 . ? C14 H14F 0.9600 . ? C15' C16' 1.353(6) . ? C15' H15A 0.9300 . ? C15 C16 1.364(6) . ? C15 H15B 0.9300 . ? C16' C17' 1.436(7) . ? C16' C18' 1.444(6) . ? C16 C17 1.444(7) . ? C16 C18 1.456(6) . ? C19 C24 1.389(6) . ? C19 C20 1.399(6) . ? C19' C20' 1.393(6) . ? C19' C24' 1.392(6) . ? C20 C21 1.380(6) . ? C20 H20A 0.9300 . ? C20' C21' 1.380(7) . ? C20' H20B 0.9300 . ? C21' C22' 1.402(7) . ? C21' H21A 0.9300 . ? C21 C22 1.396(7) . ? C21 H21B 0.9300 . ? C22' C23' 1.372(6) . ? C22' H22A 0.9300 . ? C22 C23 1.371(6) . ? C22 H22B 0.9300 . ? C23 C24 1.372(6) . ? C23 H23A 0.9300 . ? C23' C24' 1.390(6) . ? C23' H23B 0.9300 . ? 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 C1' N1' C12' 123.7(4) . . ? C1' N1' C11' 119.9(4) . . ? C12' N1' C11' 114.2(4) . . ? C1 N1 C12 120.2(4) . . ? C1 N1 C11 124.8(4) . . ? C12 N1 C11 114.0(4) . . ? C9' N2' C13' 113.6(4) . . ? C9' N2' C14' 115.8(4) . . ? C13' N2' C14' 110.1(4) . . ? C9 N2 C14 117.6(4) . . ? C9 N2 C13 115.0(4) . . ? C14 N2 C13 110.9(4) . . ? C18' N3' C19' 104.6(4) . . ? C18 N3 C19 105.6(4) . . ? C18' N4' C24' 106.3(4) . . ? C18 N4 C24 104.9(4) . . ? N1 C1 C2 119.9(4) . . ? N1 C1 C10 122.5(4) . . ? C2 C1 C10 117.3(4) . . ? N1' C1' C2' 116.7(4) . . ? N1' C1' C10' 123.3(4) . . ? C2' C1' C10' 119.7(4) . . ? C15' C2' C1' 120.7(4) . . ? C15' C2' C3' 120.6(4) . . ? C1' C2' C3' 117.7(4) . . ? C3 C2 C1 120.8(4) . . ? C3 C2 C15 119.1(4) . . ? C1 C2 C15 118.5(4) . . ? C4' C3' C2' 122.0(5) . . ? C4' C3' H3'A 119.0 . . ? C2' C3' H3'A 119.0 . . ? C4 C3 C2 120.4(5) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 120.8(5) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C3' C4' C5' 121.2(5) . . ? C3' C4' H4'A 119.4 . . ? C5' C4' H4'A 119.4 . . ? C6' C5' C10' 120.5(4) . . ? C6' C5' C4' 121.5(4) . . ? C10' C5' C4' 118.0(4) . . ? C10 C5 C4 120.1(5) . . ? C10 C5 C6 121.0(5) . . ? C4 C5 C6 118.9(5) . . ? C7' C6' C5' 121.4(5) . . ? C7' C6' H6'A 119.3 . . ? C5' C6' H6'A 119.3 . . ? C7 C6 C5 119.2(5) . . ? C7 C6 H6A 120.4 . . ? C5 C6 H6A 120.4 . . ? C6' C7' C8' 118.1(5) . . ? C6' C7' H7'A 121.0 . . ? C8' C7' H7'A 121.0 . . ? C6 C7 C8 120.6(5) . . ? C6 C7 H7A 119.7 . . ? C8 C7 H7A 119.7 . . ? C9' C8' C7' 124.0(5) . . ? C9' C8' H8'A 118.0 . . ? C7' C8' H8'A 118.0 . . ? C7 C8 C9 122.2(5) . . ? C7 C8 H8A 118.9 . . ? C9 C8 H8A 118.9 . . ? C8' C9' N2' 123.4(4) . . ? C8' C9' C10' 118.2(5) . . ? N2' C9' C10' 118.2(4) . . ? N2 C9 C8 122.3(5) . . ? N2 C9 C10 120.5(4) . . ? C8 C9 C10 117.2(5) . . ? C5 C10 C9 118.1(4) . . ? C5 C10 C1 118.5(4) . . ? C9 C10 C1 123.4(5) . . ? C1' C10' C5' 119.1(4) . . ? C1' C10' C9' 124.7(4) . . ? C5' C10' C9' 116.1(4) . . ? N1' C11' H11A 109.5 . . ? N1' C11' H11B 109.5 . . ? H11A C11' H11B 109.5 . . ? N1' C11' H11C 109.5 . . ? H11A C11' H11C 109.5 . . ? H11B C11' H11C 109.5 . . ? N1 C11 H11D 109.5 . . ? N1 C11 H11E 109.5 . . ? H11D C11 H11E 109.5 . . ? N1 C11 H11F 109.5 . . ? H11D C11 H11F 109.5 . . ? H11E C11 H11F 109.5 . . ? N1' C12' H12A 109.5 . . ? N1' C12' H12B 109.5 . . ? H12A C12' H12B 109.5 . . ? N1' C12' H12C 109.5 . . ? H12A C12' H12C 109.5 . . ? H12B C12' H12C 109.5 . . ? N1 C12 H12D 109.5 . . ? N1 C12 H12E 109.5 . . ? H12D C12 H12E 109.5 . . ? N1 C12 H12F 109.5 . . ? H12D C12 H12F 109.5 . . ? H12E C12 H12F 109.5 . . ? N2' C13' H13A 109.5 . . ? N2' C13' H13B 109.5 . . ? H13A C13' H13B 109.5 . . ? N2' C13' H13C 109.5 . . ? H13A C13' H13C 109.5 . . ? H13B C13' H13C 109.5 . . ? N2 C13 H13D 109.5 . . ? N2 C13 H13E 109.5 . . ? H13D C13 H13E 109.5 . . ? N2 C13 H13F 109.5 . . ? H13D C13 H13F 109.5 . . ? H13E C13 H13F 109.5 . . ? N2' C14' H14A 109.5 . . ? N2' C14' H14B 109.5 . . ? H14A C14' H14B 109.5 . . ? N2' C14' H14C 109.5 . . ? H14A C14' H14C 109.5 . . ? H14B C14' H14C 109.5 . . ? N2 C14 H14D 109.5 . . ? N2 C14 H14E 109.5 . . ? H14D C14 H14E 109.5 . . ? N2 C14 H14F 109.5 . . ? H14D C14 H14F 109.5 . . ? H14E C14 H14F 109.5 . . ? C16' C15' C2' 129.1(4) . . ? C16' C15' H15A 115.5 . . ? C2' C15' H15A 115.5 . . ? C16 C15 C2 130.3(5) . . ? C16 C15 H15B 114.8 . . ? C2 C15 H15B 114.8 . . ? C15' C16' C17' 120.6(5) . . ? C15' C16' C18' 123.1(4) . . ? C17' C16' C18' 116.3(4) . . ? C15 C16 C17 122.8(4) . . ? C15 C16 C18 120.1(4) . . ? C17 C16 C18 117.1(4) . . ? N5' C17' C16' 176.8(5) . . ? N5 C17 C16 177.5(5) . . ? N3' C18' N4' 112.9(4) . . ? N3' C18' C16' 124.8(4) . . ? N4' C18' C16' 122.2(4) . . ? N4 C18 N3 113.1(4) . . ? N4 C18 C16 123.3(4) . . ? N3 C18 C16 123.5(4) . . ? C24 C19 N3 106.8(4) . . ? C24 C19 C20 121.6(4) . . ? N3 C19 C20 131.6(4) . . ? N3' C19' C20' 130.2(4) . . ? N3' C19' C24' 109.8(4) . . ? C20' C19' C24' 119.9(4) . . ? C21 C20 C19 117.1(5) . . ? C21 C20 H20A 121.5 . . ? C19 C20 H20A 121.5 . . ? C21' C20' C19' 118.4(4) . . ? C21' C20' H20B 120.8 . . ? C19' C20' H20B 120.8 . . ? C20' C21' C22' 120.7(5) . . ? C20' C21' H21A 119.7 . . ? C22' C21' H21A 119.7 . . ? C20 C21 C22 120.6(5) . . ? C20 C21 H21B 119.7 . . ? C22 C21 H21B 119.7 . . ? C23' C22' C21' 121.6(5) . . ? C23' C22' H22A 119.2 . . ? C21' C22' H22A 119.2 . . ? C23 C22 C21 121.8(5) . . ? C23 C22 H22B 119.1 . . ? C21 C22 H22B 119.1 . . ? C24 C23 C22 118.2(5) . . ? C24 C23 H23A 120.9 . . ? C22 C23 H23A 120.9 . . ? C22' C23' C24' 117.2(5) . . ? C22' C23' H23B 121.4 . . ? C24' C23' H23B 121.4 . . ? C23 C24 N4 129.6(5) . . ? C23 C24 C19 120.6(4) . . ? N4 C24 C19 109.6(4) . . ? N4' C24' C23' 131.6(4) . . ? N4' C24' C19' 106.3(4) . . ? C23' C24' C19' 122.1(4) . . ? 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 C12 N1 C1 C2 134.1(5) . . . . ? C11 N1 C1 C2 -57.8(7) . . . . ? C12 N1 C1 C10 -39.3(7) . . . . ? C11 N1 C1 C10 128.7(5) . . . . ? C12' N1' C1' C2' -62.4(6) . . . . ? C11' N1' C1' C2' 135.5(5) . . . . ? C12' N1' C1' C10' 124.3(5) . . . . ? C11' N1' C1' C10' -37.7(7) . . . . ? N1' C1' C2' C15' 2.2(7) . . . . ? C10' C1' C2' C15' 175.7(4) . . . . ? N1' C1' C2' C3' -166.5(4) . . . . ? C10' C1' C2' C3' 7.1(7) . . . . ? N1 C1 C2 C3 -167.9(5) . . . . ? C10 C1 C2 C3 5.9(7) . . . . ? N1 C1 C2 C15 -2.6(7) . . . . ? C10 C1 C2 C15 171.1(4) . . . . ? C15' C2' C3' C4' -163.2(5) . . . . ? C1' C2' C3' C4' 5.5(7) . . . . ? C1 C2 C3 C4 6.3(8) . . . . ? C15 C2 C3 C4 -158.8(5) . . . . ? C2 C3 C4 C5 -9.4(8) . . . . ? C2' C3' C4' C5' -7.8(7) . . . . ? C3' C4' C5' C6' 180.0(5) . . . . ? C3' C4' C5' C10' -2.3(7) . . . . ? C3 C4 C5 C10 -0.4(8) . . . . ? C3 C4 C5 C6 179.7(5) . . . . ? C10' C5' C6' C7' -4.1(7) . . . . ? C4' C5' C6' C7' 173.6(5) . . . . ? C10 C5 C6 C7 -4.5(7) . . . . ? C4 C5 C6 C7 175.4(5) . . . . ? C5' C6' C7' C8' -5.9(7) . . . . ? C5 C6 C7 C8 -4.6(8) . . . . ? C6' C7' C8' C9' 6.4(7) . . . . ? C6 C7 C8 C9 3.8(8) . . . . ? C7' C8' C9' N2' -171.9(4) . . . . ? C7' C8' C9' C10' 3.1(7) . . . . ? C13' N2' C9' C8' 110.3(5) . . . . ? C14' N2' C9' C8' -18.6(7) . . . . ? C13' N2' C9' C10' -64.7(5) . . . . ? C14' N2' C9' C10' 166.4(4) . . . . ? C14 N2 C9 C8 -22.2(7) . . . . ? C13 N2 C9 C8 111.2(5) . . . . ? C14 N2 C9 C10 160.2(5) . . . . ? C13 N2 C9 C10 -66.4(6) . . . . ? C7 C8 C9 N2 -172.0(5) . . . . ? C7 C8 C9 C10 5.7(7) . . . . ? C4 C5 C10 C9 -166.1(5) . . . . ? C6 C5 C10 C9 13.9(7) . . . . ? C4 C5 C10 C1 12.7(7) . . . . ? C6 C5 C10 C1 -167.4(5) . . . . ? N2 C9 C10 C5 163.5(4) . . . . ? C8 C9 C10 C5 -14.2(7) . . . . ? N2 C9 C10 C1 -15.1(7) . . . . ? C8 C9 C10 C1 167.2(5) . . . . ? N1 C1 C10 C5 158.4(5) . . . . ? C2 C1 C10 C5 -15.2(7) . . . . ? N1 C1 C10 C9 -22.9(8) . . . . ? C2 C1 C10 C9 163.5(5) . . . . ? N1' C1' C10' C5' 156.1(4) . . . . ? C2' C1' C10' C5' -17.0(7) . . . . ? N1' C1' C10' C9' -24.7(7) . . . . ? C2' C1' C10' C9' 162.2(4) . . . . ? C6' C5' C10' C1' -167.7(4) . . . . ? C4' C5' C10' C1' 14.6(6) . . . . ? C6' C5' C10' C9' 13.1(6) . . . . ? C4' C5' C10' C9' -164.7(4) . . . . ? C8' C9' C10' C1' 168.3(4) . . . . ? N2' C9' C10' C1' -16.4(7) . . . . ? C8' C9' C10' C5' -12.5(6) . . . . ? N2' C9' C10' C5' 162.7(4) . . . . ? C1' C2' C15' C16' 150.8(5) . . . . ? C3' C2' C15' C16' -40.9(8) . . . . ? C3 C2 C15 C16 -31.1(8) . . . . ? C1 C2 C15 C16 163.4(5) . . . . ? C2' C15' C16' C17' -9.4(8) . . . . ? C2' C15' C16' C18' 168.8(5) . . . . ? C2 C15 C16 C17 -10.4(8) . . . . ? C2 C15 C16 C18 168.6(5) . . . . ? C15' C16' C17' N5' -62(10) . . . . ? C18' C16' C17' N5' 120(10) . . . . ? C15 C16 C17 N5 -120(12) . . . . ? C18 C16 C17 N5 61(13) . . . . ? C19' N3' C18' N4' -1.6(5) . . . . ? C19' N3' C18' C16' 176.0(4) . . . . ? C24' N4' C18' N3' 2.0(5) . . . . ? C24' N4' C18' C16' -175.6(4) . . . . ? C15' C16' C18' N3' 179.5(4) . . . . ? C17' C16' C18' N3' -2.3(7) . . . . ? C15' C16' C18' N4' -3.2(7) . . . . ? C17' C16' C18' N4' 175.1(4) . . . . ? C24 N4 C18 N3 0.4(5) . . . . ? C24 N4 C18 C16 -174.8(4) . . . . ? C19 N3 C18 N4 -1.3(5) . . . . ? C19 N3 C18 C16 173.8(4) . . . . ? C15 C16 C18 N4 -5.6(7) . . . . ? C17 C16 C18 N4 173.4(4) . . . . ? C15 C16 C18 N3 179.7(4) . . . . ? C17 C16 C18 N3 -1.3(7) . . . . ? C18 N3 C19 C24 1.7(5) . . . . ? C18 N3 C19 C20 -176.4(5) . . . . ? C18' N3' C19' C20' -177.5(5) . . . . ? C18' N3' C19' C24' 0.5(5) . . . . ? C24 C19 C20 C21 -1.7(7) . . . . ? N3 C19 C20 C21 176.2(5) . . . . ? N3' C19' C20' C21' 177.2(5) . . . . ? C24' C19' C20' C21' -0.6(7) . . . . ? C19' C20' C21' C22' -0.4(7) . . . . ? C19 C20 C21 C22 2.1(7) . . . . ? C20' C21' C22' C23' 2.0(8) . . . . ? C20 C21 C22 C23 -1.2(8) . . . . ? C21 C22 C23 C24 -0.3(7) . . . . ? C21' C22' C23' C24' -2.5(7) . . . . ? C22 C23 C24 N4 -175.0(4) . . . . ? C22 C23 C24 C19 0.8(7) . . . . ? C18 N4 C24 C23 176.9(5) . . . . ? C18 N4 C24 C19 0.8(5) . . . . ? N3 C19 C24 C23 -178.1(4) . . . . ? C20 C19 C24 C23 0.2(7) . . . . ? N3 C19 C24 N4 -1.6(5) . . . . ? C20 C19 C24 N4 176.7(4) . . . . ? C18' N4' C24' C23' 177.1(5) . . . . ? C18' N4' C24' C19' -1.6(5) . . . . ? C22' C23' C24' N4' -177.0(5) . . . . ? C22' C23' C24' C19' 1.4(7) . . . . ? N3' C19' C24' N4' 0.7(5) . . . . ? C20' C19' C24' N4' 178.9(4) . . . . ? N3' C19' C24' C23' -178.1(4) . . . . ? C20' C19' C24' C23' 0.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.443 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.064 _publ_section_references ; Bruker, Programs APEX II, version 2.0-1; SAINT, version 7.23A; SADABS, version 2004/1; XPREP, version 2005/2; SHELXTL, version 6.1. Bruker AXS Inc., Madison, WI, USA, 2005. G.M. Sheldrick, Programs SHELXS97 (crystal structure solution) and SHELXL97 (crystal structure refinement), University of Gottingen, Germany, 1997. ; #===END