Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Denat, Franck' 'Espinosa, Enrique' 'Guilard, Roger' 'Lagrange, Jean-Marie' 'Tripier, Raphael' _publ_contact_author_name 'Prof Roger Guilard' _publ_contact_author_address ; LIMSAG (UMR 5633) Université de Bourgogne Faculté des Sciences, 6, Boulevard DIJON COTE D'OR 21100 FRANCE ; # _publ_contact_author_phone '+33 3 80 39 61 11' _publ_contact_author_fax '+33 3 80 39 61 17' _publ_contact_author_email Roger.Guilard@u-bourgogne.fr _publ_requested_journal 'Chemical Communications' #=============================================================================== # TITLE _publ_section_title ; >From new tricyclic bisaminal derivatives to trans-N,N'-disubstituted cyclams. ; #======================================================================== data_rt399 _database_code_CSD 172390 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H32 N4' _chemical_formula_sum 'C24 H32 N4' _chemical_formula_weight 376.54 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/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 16.1230(3) _cell_length_b 8.68300(10) _cell_length_c 16.7890(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.3191(7) _cell_angle_gamma 90.00 _cell_volume 2069.10(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12112 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 30.08 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.072 _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 12112 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 30.08 _reflns_number_total 6062 _reflns_number_gt 4477 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. Anisotropic thermal parameters were used for non-H atoms. The H-atoms were refined with a riding model and a global isotropic thermal factor. ; _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^)+(0.0520P)^2^+0.5267P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6062 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1343 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1A N 0.02111(8) 0.85892(12) 0.07762(7) 0.0378(2) Uani 1 1 d . . . N2A N 0.15251(9) 1.01382(12) 0.14808(8) 0.0441(3) Uani 1 1 d . . . C1A C 0.04621(11) 0.85962(18) 0.17315(9) 0.0486(3) Uani 1 1 d . . . H1A H 0.0791 0.7660 0.2030 0.0577(8) Uiso 1 1 calc R . . H1B H -0.0091 0.8711 0.1813 0.0577(8) Uiso 1 1 calc R . . C2A C 0.10988(15) 0.99835(19) 0.20831(11) 0.0608(4) Uani 1 1 d . . . H2A1 H 0.0740 1.0897 0.2056 0.0577(8) Uiso 1 1 calc R . . H2A2 H 0.1580 0.9823 0.2704 0.0577(8) Uiso 1 1 calc R . . C3A C 0.16039(10) 1.17150(15) 0.12252(10) 0.0437(3) Uani 1 1 d . . . H3A H 0.1913 1.1672 0.0852 0.0577(8) Uiso 1 1 calc R . . H3B H 0.2025 1.2260 0.1774 0.0577(8) Uiso 1 1 calc R . . C4A C 0.07172(10) 1.27083(15) 0.07231(10) 0.0444(3) Uani 1 1 d . . . H4A H 0.0240 1.2320 0.0868 0.0577(8) Uiso 1 1 calc R . . H4B H 0.0869 1.3748 0.0960 0.0577(8) Uiso 1 1 calc R . . C5A C 0.02891(10) 1.27907(15) -0.02995(10) 0.0444(3) Uani 1 1 d . . . H5A H -0.0144 1.3654 -0.0515 0.0577(8) Uiso 1 1 calc R . . H5B H 0.0788 1.2995 -0.0452 0.0577(8) Uiso 1 1 calc R . . C6A C 0.10987(9) 0.89912(13) 0.07640(8) 0.0347(3) Uani 1 1 d . . . H6A H 0.0950 0.9467 0.0182 0.0577(8) Uiso 1 1 calc R . . C7A C 0.17631(9) 0.76256(14) 0.09347(9) 0.0368(3) Uani 1 1 d . . . C8A C 0.17483(10) 0.67991(16) 0.02200(10) 0.0436(3) Uani 1 1 d . . . H8A H 0.1345 0.7104 -0.0371 0.0577(8) Uiso 1 1 calc R . . C9A C 0.23262(11) 0.55229(18) 0.03714(12) 0.0537(4) Uani 1 1 d . . . H9A H 0.2305 0.4984 -0.0117 0.0577(8) Uiso 1 1 calc R . . C10A C 0.29294(11) 0.50542(18) 0.12408(14) 0.0581(4) Uani 1 1 d . . . H10A H 0.3313 0.4197 0.1343 0.0577(8) Uiso 1 1 calc R . . C11A C 0.29590(11) 0.58705(19) 0.19594(12) 0.0586(4) Uani 1 1 d . . . H11A H 0.3363 0.5560 0.2549 0.0577(8) Uiso 1 1 calc R . . C12A C 0.23898(10) 0.71505(17) 0.18081(10) 0.0489(3) Uani 1 1 d . . . H12A H 0.2428 0.7702 0.2299 0.0577(8) Uiso 1 1 calc R . . N1B N 0.08059(7) 0.15207(12) 0.52787(7) 0.0375(2) Uani 1 1 d . . . N2B N 0.10040(8) -0.00426(13) 0.42747(8) 0.0432(3) Uani 1 1 d . . . C1B C 0.18074(10) 0.15411(18) 0.55485(10) 0.0490(3) Uani 1 1 d . . . H1B1 H 0.2188 0.1484 0.6201 0.0577(8) Uiso 1 1 calc R . . H1B2 H 0.1978 0.2456 0.5328 0.0577(8) Uiso 1 1 calc R . . C2B C 0.19099(11) 0.0105(2) 0.50948(13) 0.0601(4) Uani 1 1 d . . . H2B1 H 0.2420 0.0216 0.4946 0.0577(8) Uiso 1 1 calc R . . H2B2 H 0.2032 -0.0787 0.5483 0.0577(8) Uiso 1 1 calc R . . C3B C 0.06761(10) -0.16019(15) 0.39616(9) 0.0416(3) Uani 1 1 d . . . H3B1 H 0.1122 -0.2068 0.3799 0.0577(8) Uiso 1 1 calc R . . H3B2 H 0.0082 -0.1516 0.3409 0.0577(8) Uiso 1 1 calc R . . C4B C 0.05282(11) -0.27401(16) 0.45852(10) 0.0462(3) Uani 1 1 d . . . H4B1 H 0.0727 -0.3751 0.4497 0.0577(8) Uiso 1 1 calc R . . H4B2 H 0.0945 -0.2441 0.5206 0.0577(8) Uiso 1 1 calc R . . C5B C -0.04610(11) -0.28891(15) 0.44723(10) 0.0453(3) Uani 1 1 d . . . H5B1 H -0.0890 -0.3135 0.3845 0.0577(8) Uiso 1 1 calc R . . H5B2 H -0.0472 -0.3745 0.4839 0.0577(8) Uiso 1 1 calc R . . C6B C 0.03405(9) 0.10589(13) 0.43146(8) 0.0343(3) Uani 1 1 d . . . H6B H -0.0249 0.0525 0.4172 0.0577(8) Uiso 1 1 calc R . . C7B C 0.01327(9) 0.23753(14) 0.36398(8) 0.0357(3) Uani 1 1 d . . . C8B C -0.07635(10) 0.30039(16) 0.31893(9) 0.0439(3) Uani 1 1 d . . . H8B H -0.1237 0.2608 0.3297 0.0577(8) Uiso 1 1 calc R . . C9B C -0.09715(12) 0.42126(18) 0.25800(10) 0.0549(4) Uani 1 1 d . . . H9B H -0.1577 0.4620 0.2287 0.0577(8) Uiso 1 1 calc R . . C10B C -0.02777(13) 0.48003(18) 0.24138(11) 0.0593(4) Uani 1 1 d . . . H10B H -0.0412 0.5612 0.2010 0.0577(8) Uiso 1 1 calc R . . C11B C 0.06175(13) 0.41861(19) 0.28461(11) 0.0573(4) Uani 1 1 d . . . H11B H 0.1087 0.4585 0.2733 0.0577(8) Uiso 1 1 calc R . . C12B C 0.08217(11) 0.29744(17) 0.34500(10) 0.0454(3) Uani 1 1 d . . . H12B H 0.1425 0.2557 0.3731 0.0577(8) 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 N1A 0.0440(6) 0.0341(5) 0.0374(5) 0.0060(4) 0.0210(5) 0.0045(4) N2A 0.0602(7) 0.0286(5) 0.0382(6) -0.0004(4) 0.0189(5) 0.0006(5) C1A 0.0616(9) 0.0493(8) 0.0421(7) 0.0111(6) 0.0304(7) 0.0098(7) C2A 0.1003(13) 0.0447(8) 0.0432(8) -0.0021(6) 0.0388(9) 0.0010(8) C3A 0.0431(7) 0.0295(6) 0.0490(8) -0.0030(5) 0.0141(6) -0.0023(5) C4A 0.0468(8) 0.0310(6) 0.0502(8) -0.0025(6) 0.0188(6) 0.0027(5) C5A 0.0436(7) 0.0346(7) 0.0510(8) 0.0096(6) 0.0192(6) 0.0007(6) C6A 0.0427(7) 0.0273(5) 0.0334(6) 0.0026(5) 0.0175(5) 0.0019(5) C7A 0.0380(6) 0.0286(6) 0.0438(7) 0.0023(5) 0.0195(5) -0.0006(5) C8A 0.0476(7) 0.0388(7) 0.0517(8) 0.0008(6) 0.0295(6) 0.0009(6) C9A 0.0555(9) 0.0413(8) 0.0785(11) -0.0076(7) 0.0434(9) -0.0002(7) C10A 0.0442(8) 0.0388(8) 0.0916(13) 0.0053(8) 0.0324(8) 0.0088(6) C11A 0.0465(8) 0.0464(8) 0.0658(10) 0.0091(7) 0.0126(7) 0.0091(7) C12A 0.0477(8) 0.0408(7) 0.0471(8) 0.0022(6) 0.0134(6) 0.0058(6) N1B 0.0397(6) 0.0337(5) 0.0385(5) 0.0020(4) 0.0180(5) -0.0023(4) N2B 0.0412(6) 0.0337(5) 0.0560(7) 0.0003(5) 0.0240(5) 0.0031(5) C1B 0.0403(7) 0.0508(8) 0.0499(8) 0.0001(7) 0.0165(6) -0.0091(6) C2B 0.0364(7) 0.0548(9) 0.0794(12) -0.0041(8) 0.0195(8) 0.0029(7) C3B 0.0531(8) 0.0346(6) 0.0441(7) -0.0002(5) 0.0288(6) 0.0053(6) C4B 0.0603(9) 0.0336(7) 0.0521(8) 0.0068(6) 0.0326(7) 0.0115(6) C5B 0.0619(9) 0.0320(6) 0.0470(7) -0.0021(5) 0.0298(7) -0.0050(6) C6B 0.0351(6) 0.0270(6) 0.0406(6) 0.0015(5) 0.0179(5) -0.0012(5) C7B 0.0430(7) 0.0291(6) 0.0343(6) -0.0022(5) 0.0177(5) -0.0045(5) C8B 0.0437(7) 0.0401(7) 0.0403(7) 0.0041(6) 0.0138(6) -0.0031(6) C9B 0.0581(9) 0.0437(8) 0.0427(7) 0.0065(6) 0.0074(7) 0.0005(7) C10B 0.0805(12) 0.0427(8) 0.0429(8) 0.0092(6) 0.0196(8) -0.0115(8) C11B 0.0756(11) 0.0513(9) 0.0524(9) 0.0023(7) 0.0364(8) -0.0173(8) C12B 0.0519(8) 0.0413(7) 0.0471(7) -0.0003(6) 0.0268(6) -0.0056(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1A C5A 1.4541(18) 3_575 ? N1A C1A 1.4561(17) . ? N1A C6A 1.4825(17) . ? N2A C3A 1.4583(17) . ? N2A C6A 1.4587(16) . ? N2A C2A 1.474(2) . ? C1A C2A 1.509(2) . ? C1A H1A 0.9700 . ? C1A H1B 0.9700 . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3A C4A 1.5346(19) . ? C3A H3A 0.9700 . ? C3A H3B 0.9700 . ? C4A C5A 1.518(2) . ? C4A H4A 0.9700 . ? C4A H4B 0.9700 . ? C5A N1A 1.4541(18) 3_575 ? C5A H5A 0.9700 . ? C5A H5B 0.9700 . ? C6A C7A 1.5311(17) . ? C6A H6A 0.9800 . ? C7A C8A 1.3887(19) . ? C7A C12A 1.3912(19) . ? C8A C9A 1.391(2) . ? C8A H8A 0.9300 . ? C9A C10A 1.377(3) . ? C9A H9A 0.9300 . ? C10A C11A 1.380(3) . ? C10A H10A 0.9300 . ? C11A C12A 1.386(2) . ? C11A H11A 0.9300 . ? C12A H12A 0.9300 . ? N1B C5B 1.4547(17) 3_556 ? N1B C1B 1.4557(17) . ? N1B C6B 1.4804(16) . ? N2B C3B 1.4579(17) . ? N2B C6B 1.4601(16) . ? N2B C2B 1.462(2) . ? C1B C2B 1.510(2) . ? C1B H1B1 0.9700 . ? C1B H1B2 0.9700 . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C4B 1.5384(19) . ? C3B H3B1 0.9700 . ? C3B H3B2 0.9700 . ? C4B C5B 1.520(2) . ? C4B H4B1 0.9700 . ? C4B H4B2 0.9700 . ? C5B N1B 1.4547(17) 3_556 ? C5B H5B1 0.9700 . ? C5B H5B2 0.9700 . ? C6B C7B 1.5304(17) . ? C6B H6B 0.9800 . ? C7B C8B 1.3860(19) . ? C7B C12B 1.3935(19) . ? C8B C9B 1.391(2) . ? C8B H8B 0.9300 . ? C9B C10B 1.373(2) . ? C9B H9B 0.9300 . ? C10B C11B 1.379(3) . ? C10B H10B 0.9300 . ? C11B C12B 1.388(2) . ? C11B H11B 0.9300 . ? C12B H12B 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 C5A N1A C1A 113.67(11) 3_575 . ? C5A N1A C6A 118.25(10) 3_575 . ? C1A N1A C6A 104.39(10) . . ? C3A N2A C6A 118.09(11) . . ? C3A N2A C2A 114.93(12) . . ? C6A N2A C2A 108.25(11) . . ? N1A C1A C2A 102.49(11) . . ? N1A C1A H1A 111.3 . . ? C2A C1A H1A 111.3 . . ? N1A C1A H1B 111.3 . . ? C2A C1A H1B 111.3 . . ? H1A C1A H1B 109.2 . . ? N2A C2A C1A 104.85(12) . . ? N2A C2A H2A1 110.8 . . ? C1A C2A H2A1 110.8 . . ? N2A C2A H2A2 110.8 . . ? C1A C2A H2A2 110.8 . . ? H2A1 C2A H2A2 108.9 . . ? N2A C3A C4A 120.05(12) . . ? N2A C3A H3A 107.3 . . ? C4A C3A H3A 107.3 . . ? N2A C3A H3B 107.3 . . ? C4A C3A H3B 107.3 . . ? H3A C3A H3B 106.9 . . ? C5A C4A C3A 116.93(12) . . ? C5A C4A H4A 108.1 . . ? C3A C4A H4A 108.1 . . ? C5A C4A H4B 108.1 . . ? C3A C4A H4B 108.1 . . ? H4A C4A H4B 107.3 . . ? N1A C5A C4A 114.81(11) 3_575 . ? N1A C5A H5A 108.6 3_575 . ? C4A C5A H5A 108.6 . . ? N1A C5A H5B 108.6 3_575 . ? C4A C5A H5B 108.6 . . ? H5A C5A H5B 107.5 . . ? N2A C6A N1A 103.27(10) . . ? N2A C6A C7A 111.12(10) . . ? N1A C6A C7A 114.16(10) . . ? N2A C6A H6A 109.4 . . ? N1A C6A H6A 109.4 . . ? C7A C6A H6A 109.4 . . ? C8A C7A C12A 117.62(13) . . ? C8A C7A C6A 120.98(12) . . ? C12A C7A C6A 121.39(12) . . ? C7A C8A C9A 121.21(14) . . ? C7A C8A H8A 119.4 . . ? C9A C8A H8A 119.4 . . ? C10A C9A C8A 120.28(15) . . ? C10A C9A H9A 119.9 . . ? C8A C9A H9A 119.9 . . ? C9A C10A C11A 119.27(14) . . ? C9A C10A H10A 120.4 . . ? C11A C10A H10A 120.4 . . ? C10A C11A C12A 120.41(16) . . ? C10A C11A H11A 119.8 . . ? C12A C11A H11A 119.8 . . ? C11A C12A C7A 121.18(15) . . ? C11A C12A H12A 119.4 . . ? C7A C12A H12A 119.4 . . ? C5B N1B C1B 114.80(11) 3_556 . ? C5B N1B C6B 118.09(10) 3_556 . ? C1B N1B C6B 104.81(10) . . ? C3B N2B C6B 118.46(11) . . ? C3B N2B C2B 116.78(12) . . ? C6B N2B C2B 109.00(11) . . ? N1B C1B C2B 101.75(11) . . ? N1B C1B H1B1 111.4 . . ? C2B C1B H1B1 111.4 . . ? N1B C1B H1B2 111.4 . . ? C2B C1B H1B2 111.4 . . ? H1B1 C1B H1B2 109.3 . . ? N2B C2B C1B 104.36(12) . . ? N2B C2B H2B1 110.9 . . ? C1B C2B H2B1 110.9 . . ? N2B C2B H2B2 110.9 . . ? C1B C2B H2B2 110.9 . . ? H2B1 C2B H2B2 108.9 . . ? N2B C3B C4B 119.87(11) . . ? N2B C3B H3B1 107.4 . . ? C4B C3B H3B1 107.4 . . ? N2B C3B H3B2 107.4 . . ? C4B C3B H3B2 107.4 . . ? H3B1 C3B H3B2 106.9 . . ? C5B C4B C3B 117.52(12) . . ? C5B C4B H4B1 107.9 . . ? C3B C4B H4B1 107.9 . . ? C5B C4B H4B2 107.9 . . ? C3B C4B H4B2 107.9 . . ? H4B1 C4B H4B2 107.2 . . ? N1B C5B C4B 114.59(11) 3_556 . ? N1B C5B H5B1 108.6 3_556 . ? C4B C5B H5B1 108.6 . . ? N1B C5B H5B2 108.6 3_556 . ? C4B C5B H5B2 108.6 . . ? H5B1 C5B H5B2 107.6 . . ? N2B C6B N1B 103.02(10) . . ? N2B C6B C7B 111.29(10) . . ? N1B C6B C7B 115.25(10) . . ? N2B C6B H6B 109.0 . . ? N1B C6B H6B 109.0 . . ? C7B C6B H6B 109.0 . . ? C8B C7B C12B 117.78(12) . . ? C8B C7B C6B 120.23(11) . . ? C12B C7B C6B 121.99(12) . . ? C7B C8B C9B 121.58(14) . . ? C7B C8B H8B 119.2 . . ? C9B C8B H8B 119.2 . . ? C10B C9B C8B 119.63(15) . . ? C10B C9B H9B 120.2 . . ? C8B C9B H9B 120.2 . . ? C9B C10B C11B 119.97(14) . . ? C9B C10B H10B 120.0 . . ? C11B C10B H10B 120.0 . . ? C10B C11B C12B 120.27(15) . . ? C10B C11B H11B 119.9 . . ? C12B C11B H11B 119.9 . . ? C11B C12B C7B 120.76(15) . . ? C11B C12B H12B 119.6 . . ? C7B C12B H12B 119.6 . . ? 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 C5A N1A C1A C2A 170.85(12) 3_575 . . . ? C6A N1A C1A C2A 40.61(14) . . . . ? C3A N2A C2A C1A 139.26(12) . . . . ? C6A N2A C2A C1A 4.82(16) . . . . ? N1A C1A C2A N2A -27.86(16) . . . . ? C6A N2A C3A C4A 70.34(17) . . . . ? C2A N2A C3A C4A -59.43(18) . . . . ? N2A C3A C4A C5A -96.99(16) . . . . ? C3A C4A C5A N1A 74.09(16) . . . 3_575 ? C3A N2A C6A N1A -113.07(12) . . . . ? C2A N2A C6A N1A 19.71(13) . . . . ? C3A N2A C6A C7A 124.12(12) . . . . ? C2A N2A C6A C7A -103.10(13) . . . . ? C5A N1A C6A N2A -165.31(10) 3_575 . . . ? C1A N1A C6A N2A -37.84(12) . . . . ? C5A N1A C6A C7A -44.55(15) 3_575 . . . ? C1A N1A C6A C7A 82.92(13) . . . . ? N2A C6A C7A C8A -149.42(12) . . . . ? N1A C6A C7A C8A 94.30(14) . . . . ? N2A C6A C7A C12A 31.76(17) . . . . ? N1A C6A C7A C12A -84.52(15) . . . . ? C12A C7A C8A C9A 1.2(2) . . . . ? C6A C7A C8A C9A -177.62(12) . . . . ? C7A C8A C9A C10A -0.1(2) . . . . ? C8A C9A C10A C11A -0.5(2) . . . . ? C9A C10A C11A C12A -0.2(2) . . . . ? C10A C11A C12A C7A 1.4(3) . . . . ? C8A C7A C12A C11A -1.9(2) . . . . ? C6A C7A C12A C11A 176.98(13) . . . . ? C5B N1B C1B C2B -172.86(12) 3_556 . . . ? C6B N1B C1B C2B -41.67(14) . . . . ? C3B N2B C2B C1B -147.45(12) . . . . ? C6B N2B C2B C1B -9.85(16) . . . . ? N1B C1B C2B N2B 31.38(16) . . . . ? C6B N2B C3B C4B -74.69(16) . . . . ? C2B N2B C3B C4B 58.82(18) . . . . ? N2B C3B C4B C5B 95.49(16) . . . . ? C3B C4B C5B N1B -66.80(16) . . . 3_556 ? C3B N2B C6B N1B 121.50(12) . . . . ? C2B N2B C6B N1B -15.29(14) . . . . ? C3B N2B C6B C7B -114.45(12) . . . . ? C2B N2B C6B C7B 108.76(13) . . . . ? C5B N1B C6B N2B 165.05(10) 3_556 . . . ? C1B N1B C6B N2B 35.79(12) . . . . ? C5B N1B C6B C7B 43.64(15) 3_556 . . . ? C1B N1B C6B C7B -85.62(13) . . . . ? N2B C6B C7B C8B 143.49(12) . . . . ? N1B C6B C7B C8B -99.71(14) . . . . ? N2B C6B C7B C12B -36.00(16) . . . . ? N1B C6B C7B C12B 80.80(15) . . . . ? C12B C7B C8B C9B -1.2(2) . . . . ? C6B C7B C8B C9B 179.26(13) . . . . ? C7B C8B C9B C10B 0.3(2) . . . . ? C8B C9B C10B C11B 0.4(2) . . . . ? C9B C10B C11B C12B 0.0(2) . . . . ? C10B C11B C12B C7B -1.0(2) . . . . ? C8B C7B C12B C11B 1.6(2) . . . . ? C6B C7B C12B C11B -178.91(13) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.08 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.241 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.035 data_rt457 _database_code_CSD 172391 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H30 N6' _chemical_formula_sum 'C22 H30 N6' _chemical_formula_weight 378.52 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' 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 12.3990(2) _cell_length_b 12.8130(2) _cell_length_c 12.5250(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.3540(7) _cell_angle_gamma 90.00 _cell_volume 1977.60(5) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 27316 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 38.60 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.94 _exptl_crystal_size_mid 0.68 _exptl_crystal_size_min 0.60 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.079 _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 110(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 27316 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 38.60 _reflns_number_total 11105 _reflns_number_gt 9522 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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. Anisotropic thermal parameters were used for non-H atoms. The H-atoms were refined with a riding model and a global isotropic thermal factor. ; _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^)+(0.0520P)^2^+0.6176P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11105 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1260 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1A N 0.00955(5) 0.38181(4) 0.05900(5) 0.01221(9) Uani 1 1 d . . . N2A N 0.08977(5) 0.61519(4) 0.11784(4) 0.01236(9) Uani 1 1 d . . . N8A N 0.19113(5) 0.67114(5) -0.13614(5) 0.01493(10) Uani 1 1 d . . . C1A C 0.03642(6) 0.43052(6) 0.16471(5) 0.01507(11) Uani 1 1 d . . . H1A1 H 0.1127 0.4182 0.1876 0.0235(6) Uiso 1 1 calc R . . H1A2 H -0.0049 0.3957 0.2156 0.0235(6) Uiso 1 1 calc R . . C2A C 0.01513(6) 0.54787(5) 0.17058(5) 0.01420(11) Uani 1 1 d . . . H2A1 H -0.0583 0.5614 0.1383 0.0235(6) Uiso 1 1 calc R . . H2A2 H 0.0189 0.5678 0.2456 0.0235(6) Uiso 1 1 calc R . . C3A C 0.06359(6) 0.72660(5) 0.13081(6) 0.01547(11) Uani 1 1 d . . . H3A1 H 0.1244 0.7683 0.1131 0.0235(6) Uiso 1 1 calc R . . H3A2 H 0.0545 0.7395 0.2056 0.0235(6) Uiso 1 1 calc R . . C4A C -0.03926(6) 0.76263(6) 0.06079(6) 0.01755(12) Uani 1 1 d . . . H4A1 H -0.1027 0.7322 0.0876 0.0235(6) Uiso 1 1 calc R . . H4A2 H -0.0454 0.8380 0.0647 0.0235(6) Uiso 1 1 calc R . . C5A C -0.03494(6) 0.72955(5) -0.05605(6) 0.01530(11) Uani 1 1 d . . . H5A1 H -0.1043 0.7430 -0.0975 0.0235(6) Uiso 1 1 calc R . . H5A2 H 0.0202 0.7694 -0.0872 0.0235(6) Uiso 1 1 calc R . . C6A C 0.09372(5) 0.59228(5) 0.00370(5) 0.01135(9) Uani 1 1 d . . . H6A H 0.1026 0.5166 -0.0019 0.0235(6) Uiso 1 1 calc R . . C7A C 0.19593(5) 0.64181(5) -0.03289(5) 0.01185(10) Uani 1 1 d . . . C9A C 0.28273(6) 0.70631(6) -0.17203(6) 0.01757(12) Uani 1 1 d . . . H9A H 0.2794 0.7279 -0.2432 0.0235(6) Uiso 1 1 calc R . . C10A C 0.38195(6) 0.71237(6) -0.10922(7) 0.01914(13) Uani 1 1 d . . . H10A H 0.4435 0.7365 -0.1377 0.0235(6) Uiso 1 1 calc R . . C11A C 0.38671(6) 0.68124(6) -0.00215(6) 0.01843(12) Uani 1 1 d . . . H11A H 0.4519 0.6837 0.0424 0.0235(6) Uiso 1 1 calc R . . C12A C 0.29241(5) 0.64654(5) 0.03681(6) 0.01481(11) Uani 1 1 d . . . H12A H 0.2933 0.6267 0.1083 0.0235(6) Uiso 1 1 calc R . . N1B N 0.61361(5) 0.51063(5) 0.58860(5) 0.01317(9) Uani 1 1 d . . . N2B N 0.36338(5) 0.44531(5) 0.59439(5) 0.01328(9) Uani 1 1 d . . . N8B N 0.35700(5) 0.27214(5) 0.36209(5) 0.01615(10) Uani 1 1 d . . . C1B C 0.54694(6) 0.51238(6) 0.67840(5) 0.01593(11) Uani 1 1 d . . . H1B1 H 0.5751 0.5661 0.7286 0.0235(6) Uiso 1 1 calc R . . H1B2 H 0.5553 0.4460 0.7156 0.0235(6) Uiso 1 1 calc R . . C2B C 0.42569(6) 0.53224(5) 0.64834(6) 0.01507(11) Uani 1 1 d . . . H2B1 H 0.3936 0.5495 0.7133 0.0235(6) Uiso 1 1 calc R . . H2B2 H 0.4176 0.5928 0.6017 0.0235(6) Uiso 1 1 calc R . . C3B C 0.24695(6) 0.47151(6) 0.57358(6) 0.01773(12) Uani 1 1 d . . . H3B1 H 0.2237 0.5029 0.6377 0.0235(6) Uiso 1 1 calc R . . H3B2 H 0.2060 0.4076 0.5595 0.0235(6) Uiso 1 1 calc R . . C4B C 0.21988(6) 0.54646(6) 0.47873(7) 0.02017(13) Uani 1 1 d . . . H4B1 H 0.1418 0.5511 0.4618 0.0235(6) Uiso 1 1 calc R . . H4B2 H 0.2471 0.6156 0.4984 0.0235(6) Uiso 1 1 calc R . . C5B C 0.27093(6) 0.50810(6) 0.38018(6) 0.01764(12) Uani 1 1 d . . . H5B1 H 0.2359 0.4442 0.3533 0.0235(6) Uiso 1 1 calc R . . H5B2 H 0.2616 0.5601 0.3237 0.0235(6) Uiso 1 1 calc R . . C6B C 0.40413(5) 0.40954(5) 0.49523(5) 0.01155(10) Uani 1 1 d . . . H6B H 0.4829 0.4024 0.5115 0.0235(6) Uiso 1 1 calc R . . C7B C 0.36044(5) 0.29991(5) 0.46582(5) 0.01197(10) Uani 1 1 d . . . C9B C 0.33103(7) 0.17262(6) 0.33606(6) 0.01869(13) Uani 1 1 d . . . H9B H 0.3286 0.1531 0.2643 0.0235(6) Uiso 1 1 calc R . . C10B C 0.30775(7) 0.09747(6) 0.40973(6) 0.01787(12) Uani 1 1 d . . . H10B H 0.2909 0.0294 0.3881 0.0235(6) Uiso 1 1 calc R . . C11B C 0.31025(6) 0.12674(5) 0.51678(6) 0.01660(11) Uani 1 1 d . . . H11B H 0.2944 0.0787 0.5685 0.0235(6) Uiso 1 1 calc R . . C12B C 0.33683(6) 0.22910(5) 0.54524(6) 0.01419(11) Uani 1 1 d . . . H12B H 0.3389 0.2504 0.6164 0.0235(6) 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 N1A 0.0118(2) 0.0116(2) 0.0125(2) 0.00016(16) -0.00156(16) -0.00040(16) N2A 0.0142(2) 0.0116(2) 0.0112(2) -0.00163(16) 0.00078(16) -0.00159(17) N8A 0.0140(2) 0.0158(2) 0.0150(2) 0.00245(18) 0.00170(17) -0.00062(18) C1A 0.0177(3) 0.0153(3) 0.0114(2) 0.00162(19) -0.00198(19) -0.0032(2) C2A 0.0157(2) 0.0156(3) 0.0113(2) -0.00154(19) 0.00167(19) -0.0027(2) C3A 0.0169(3) 0.0128(2) 0.0165(3) -0.0036(2) 0.0008(2) -0.0004(2) C4A 0.0172(3) 0.0146(3) 0.0207(3) -0.0027(2) 0.0013(2) 0.0030(2) C5A 0.0151(3) 0.0122(2) 0.0182(3) 0.0012(2) -0.0001(2) 0.0012(2) C6A 0.0117(2) 0.0106(2) 0.0114(2) -0.00016(17) -0.00012(17) -0.00066(18) C7A 0.0115(2) 0.0101(2) 0.0137(2) -0.00049(18) 0.00051(18) -0.00039(18) C9A 0.0162(3) 0.0190(3) 0.0180(3) 0.0032(2) 0.0039(2) -0.0013(2) C10A 0.0144(3) 0.0200(3) 0.0234(3) 0.0011(2) 0.0041(2) -0.0027(2) C11A 0.0135(3) 0.0192(3) 0.0222(3) -0.0002(2) 0.0002(2) -0.0023(2) C12A 0.0133(2) 0.0147(3) 0.0160(3) -0.0003(2) -0.00052(19) -0.0009(2) N1B 0.0142(2) 0.0122(2) 0.0126(2) 0.00153(17) -0.00077(17) -0.00142(17) N2B 0.0147(2) 0.0116(2) 0.0138(2) -0.00197(17) 0.00301(17) -0.00188(17) N8B 0.0232(3) 0.0121(2) 0.0130(2) -0.00134(17) 0.00121(19) -0.00290(19) C1B 0.0205(3) 0.0159(3) 0.0110(2) 0.0001(2) 0.0004(2) -0.0046(2) C2B 0.0194(3) 0.0123(2) 0.0141(2) -0.0029(2) 0.0045(2) -0.0033(2) C3B 0.0150(3) 0.0155(3) 0.0235(3) -0.0017(2) 0.0056(2) -0.0005(2) C4B 0.0156(3) 0.0162(3) 0.0284(4) 0.0004(3) 0.0014(2) 0.0024(2) C5B 0.0168(3) 0.0146(3) 0.0201(3) 0.0017(2) -0.0039(2) -0.0002(2) C6B 0.0132(2) 0.0101(2) 0.0112(2) -0.00043(17) 0.00100(17) -0.00142(18) C7B 0.0127(2) 0.0101(2) 0.0130(2) -0.00067(18) 0.00082(18) -0.00095(18) C9B 0.0280(3) 0.0135(3) 0.0146(3) -0.0025(2) 0.0022(2) -0.0042(2) C10B 0.0241(3) 0.0113(2) 0.0184(3) -0.0021(2) 0.0035(2) -0.0037(2) C11B 0.0208(3) 0.0119(2) 0.0176(3) 0.0005(2) 0.0044(2) -0.0030(2) C12B 0.0166(3) 0.0119(2) 0.0144(2) -0.00070(19) 0.00308(19) -0.00160(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 N1A C5A 1.4625(9) 3_565 ? N1A C6A 1.4642(8) 3_565 ? N1A C1A 1.4682(9) . ? N2A C6A 1.4656(8) . ? N2A C2A 1.4738(9) . ? N2A C3A 1.4769(9) . ? N8A C7A 1.3417(9) . ? N8A C9A 1.3447(9) . ? C1A C2A 1.5298(10) . ? C1A H1A1 0.9700 . ? C1A H1A2 0.9700 . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3A C4A 1.5366(10) . ? C3A H3A1 0.9700 . ? C3A H3A2 0.9700 . ? C4A C5A 1.5301(11) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C5A N1A 1.4625(9) 3_565 ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A N1A 1.4642(8) 3_565 ? C6A C7A 1.5322(9) . ? C6A H6A 0.9800 . ? C7A C12A 1.4020(9) . ? C9A C10A 1.3871(11) . ? C9A H9A 0.9300 . ? C10A C11A 1.3941(11) . ? C10A H10A 0.9300 . ? C11A C12A 1.3890(10) . ? C11A H11A 0.9300 . ? C12A H12A 0.9300 . ? N1B C5B 1.4615(9) 3_666 ? N1B C6B 1.4649(9) 3_666 ? N1B C1B 1.4680(9) . ? N2B C6B 1.4651(8) . ? N2B C2B 1.4760(9) . ? N2B C3B 1.4769(9) . ? N8B C7B 1.3432(9) . ? N8B C9B 1.3463(9) . ? C1B C2B 1.5302(11) . ? C1B H1B1 0.9700 . ? C1B H1B2 0.9700 . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C4B 1.5356(11) . ? C3B H3B1 0.9700 . ? C3B H3B2 0.9700 . ? C4B C5B 1.5293(12) . ? C4B H4B1 0.9700 . ? C4B H4B2 0.9700 . ? C5B N1B 1.4615(9) 3_666 ? C5B H5B1 0.9700 . ? C5B H5B2 0.9700 . ? C6B N1B 1.4649(9) 3_666 ? C6B C7B 1.5357(9) . ? C6B H6B 0.9800 . ? C7B C12B 1.4010(9) . ? C9B C10B 1.3860(11) . ? C9B H9B 0.9300 . ? C10B C11B 1.3893(10) . ? C10B H10B 0.9300 . ? C11B C12B 1.3892(10) . ? C11B H11B 0.9300 . ? C12B H12B 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 C5A N1A C6A 112.68(5) 3_565 3_565 ? C5A N1A C1A 114.18(5) 3_565 . ? C6A N1A C1A 119.01(5) 3_565 . ? C6A N2A C2A 114.23(5) . . ? C6A N2A C3A 109.41(5) . . ? C2A N2A C3A 111.09(5) . . ? C7A N8A C9A 117.84(6) . . ? N1A C1A C2A 115.98(5) . . ? N1A C1A H1A1 108.3 . . ? C2A C1A H1A1 108.3 . . ? N1A C1A H1A2 108.3 . . ? C2A C1A H1A2 108.3 . . ? H1A1 C1A H1A2 107.4 . . ? N2A C2A C1A 115.69(6) . . ? N2A C2A H2A1 108.4 . . ? C1A C2A H2A1 108.4 . . ? N2A C2A H2A2 108.4 . . ? C1A C2A H2A2 108.4 . . ? H2A1 C2A H2A2 107.4 . . ? N2A C3A C4A 113.97(6) . . ? N2A C3A H3A1 108.8 . . ? C4A C3A H3A1 108.8 . . ? N2A C3A H3A2 108.8 . . ? C4A C3A H3A2 108.8 . . ? H3A1 C3A H3A2 107.7 . . ? C5A C4A C3A 110.36(6) . . ? C5A C4A H4A1 109.6 . . ? C3A C4A H4A1 109.6 . . ? C5A C4A H4A2 109.6 . . ? C3A C4A H4A2 109.6 . . ? H4A1 C4A H4A2 108.1 . . ? N1A C5A C4A 108.96(6) 3_565 . ? N1A C5A H5A1 109.9 3_565 . ? C4A C5A H5A1 109.9 . . ? N1A C5A H5A2 109.9 3_565 . ? C4A C5A H5A2 109.9 . . ? H5A1 C5A H5A2 108.3 . . ? N1A C6A N2A 110.87(5) 3_565 . ? N1A C6A C7A 116.67(5) 3_565 . ? N2A C6A C7A 109.07(5) . . ? N1A C6A H6A 106.6 3_565 . ? N2A C6A H6A 106.6 . . ? C7A C6A H6A 106.6 . . ? N8A C7A C12A 122.14(6) . . ? N8A C7A C6A 117.02(6) . . ? C12A C7A C6A 120.58(6) . . ? N8A C9A C10A 123.92(7) . . ? N8A C9A H9A 118.0 . . ? C10A C9A H9A 118.0 . . ? C9A C10A C11A 118.03(7) . . ? C9A C10A H10A 121.0 . . ? C11A C10A H10A 121.0 . . ? C12A C11A C10A 118.81(7) . . ? C12A C11A H11A 120.6 . . ? C10A C11A H11A 120.6 . . ? C11A C12A C7A 119.24(7) . . ? C11A C12A H12A 120.4 . . ? C7A C12A H12A 120.4 . . ? C5B N1B C6B 111.81(5) 3_666 3_666 ? C5B N1B C1B 114.55(6) 3_666 . ? C6B N1B C1B 119.07(6) 3_666 . ? C6B N2B C2B 114.33(5) . . ? C6B N2B C3B 110.09(5) . . ? C2B N2B C3B 111.17(6) . . ? C7B N8B C9B 117.79(6) . . ? N1B C1B C2B 115.80(6) . . ? N1B C1B H1B1 108.3 . . ? C2B C1B H1B1 108.3 . . ? N1B C1B H1B2 108.3 . . ? C2B C1B H1B2 108.3 . . ? H1B1 C1B H1B2 107.4 . . ? N2B C2B C1B 115.93(6) . . ? N2B C2B H2B1 108.3 . . ? C1B C2B H2B1 108.3 . . ? N2B C2B H2B2 108.3 . . ? C1B C2B H2B2 108.3 . . ? H2B1 C2B H2B2 107.4 . . ? N2B C3B C4B 113.85(6) . . ? N2B C3B H3B1 108.8 . . ? C4B C3B H3B1 108.8 . . ? N2B C3B H3B2 108.8 . . ? C4B C3B H3B2 108.8 . . ? H3B1 C3B H3B2 107.7 . . ? C5B C4B C3B 110.42(6) . . ? C5B C4B H4B1 109.6 . . ? C3B C4B H4B1 109.6 . . ? C5B C4B H4B2 109.6 . . ? C3B C4B H4B2 109.6 . . ? H4B1 C4B H4B2 108.1 . . ? N1B C5B C4B 108.51(6) 3_666 . ? N1B C5B H5B1 110.0 3_666 . ? C4B C5B H5B1 110.0 . . ? N1B C5B H5B2 110.0 3_666 . ? C4B C5B H5B2 110.0 . . ? H5B1 C5B H5B2 108.4 . . ? N1B C6B N2B 110.53(5) 3_666 . ? N1B C6B C7B 116.47(5) 3_666 . ? N2B C6B C7B 110.11(5) . . ? N1B C6B H6B 106.4 3_666 . ? N2B C6B H6B 106.4 . . ? C7B C6B H6B 106.4 . . ? N8B C7B C12B 121.90(6) . . ? N8B C7B C6B 116.55(6) . . ? C12B C7B C6B 121.19(6) . . ? N8B C9B C10B 123.97(7) . . ? N8B C9B H9B 118.0 . . ? C10B C9B H9B 118.0 . . ? C9B C10B C11B 118.09(6) . . ? C9B C10B H10B 121.0 . . ? C11B C10B H10B 121.0 . . ? C12B C11B C10B 118.80(6) . . ? C12B C11B H11B 120.6 . . ? C10B C11B H11B 120.6 . . ? C11B C12B C7B 119.44(6) . . ? C11B C12B H12B 120.3 . . ? C7B C12B H12B 120.3 . . ? 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 C5A N1A C1A C2A 177.82(6) 3_565 . . . ? C6A N1A C1A C2A -45.12(8) 3_565 . . . ? C6A N2A C2A C1A 57.11(7) . . . . ? C3A N2A C2A C1A -178.55(5) . . . . ? N1A C1A C2A N2A -71.71(8) . . . . ? C6A N2A C3A C4A 53.19(7) . . . . ? C2A N2A C3A C4A -73.84(7) . . . . ? N2A C3A C4A C5A -50.44(8) . . . . ? C3A C4A C5A N1A 50.91(8) . . . 3_565 ? C2A N2A C6A N1A 67.34(7) . . . 3_565 ? C3A N2A C6A N1A -57.90(7) . . . 3_565 ? C2A N2A C6A C7A -162.87(5) . . . . ? C3A N2A C6A C7A 71.90(6) . . . . ? C9A N8A C7A C12A -0.25(10) . . . . ? C9A N8A C7A C6A -174.31(6) . . . . ? N1A C6A C7A N8A -23.98(8) 3_565 . . . ? N2A C6A C7A N8A -150.52(6) . . . . ? N1A C6A C7A C12A 161.85(6) 3_565 . . . ? N2A C6A C7A C12A 35.31(8) . . . . ? C7A N8A C9A C10A 1.11(11) . . . . ? N8A C9A C10A C11A -0.75(12) . . . . ? C9A C10A C11A C12A -0.48(12) . . . . ? C10A C11A C12A C7A 1.27(11) . . . . ? N8A C7A C12A C11A -0.94(10) . . . . ? C6A C7A C12A C11A 172.92(6) . . . . ? C5B N1B C1B C2B 179.79(6) 3_666 . . . ? C6B N1B C1B C2B 43.63(8) 3_666 . . . ? C6B N2B C2B C1B -57.09(8) . . . . ? C3B N2B C2B C1B 177.50(6) . . . . ? N1B C1B C2B N2B 72.60(8) . . . . ? C6B N2B C3B C4B -51.67(8) . . . . ? C2B N2B C3B C4B 76.07(8) . . . . ? N2B C3B C4B C5B 49.61(8) . . . . ? C3B C4B C5B N1B -52.24(8) . . . 3_666 ? C2B N2B C6B N1B -68.43(7) . . . 3_666 ? C3B N2B C6B N1B 57.54(7) . . . 3_666 ? C2B N2B C6B C7B 161.49(6) . . . . ? C3B N2B C6B C7B -72.54(7) . . . . ? C9B N8B C7B C12B -0.72(11) . . . . ? C9B N8B C7B C6B 172.49(7) . . . . ? N1B C6B C7B N8B 29.97(8) 3_666 . . . ? N2B C6B C7B N8B 156.80(6) . . . . ? N1B C6B C7B C12B -156.76(6) 3_666 . . . ? N2B C6B C7B C12B -29.93(8) . . . . ? C7B N8B C9B C10B -0.01(12) . . . . ? N8B C9B C10B C11B 0.68(13) . . . . ? C9B C10B C11B C12B -0.62(11) . . . . ? C10B C11B C12B C7B -0.05(11) . . . . ? N8B C7B C12B C11B 0.76(11) . . . . ? C6B C7B C12B C11B -172.14(6) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 38.60 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.538 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.059