# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Nial Wheate' _publ_contact_author_email nial.wheate@sydney.edu.au loop_ _publ_author_name 'Sarah Brown' 'Katherine Trotter' 'Oliver Sutcliffe' 'Jane Plumb' 'Bruce Waddell' 'Naomi Briggs' ; N.Wheate ; data_try3ak _database_code_depnum_ccdc_archive 'CCDC 870360' #TrackingRef 'SCXD-of-ligand.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,:'-(butane-1,4-diyl)bis(2-methylisonicotinamide) ; _chemical_name_common N,:'-(butane-1,4-diyl)bis(2-methylisonicotinamide) _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N4 O2, C18 H22 N4 O2, 4(H2 O), 2(H)' _chemical_formula_sum 'C36 H52 N8 O8' _chemical_formula_weight 725.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3486(3) _cell_length_b 12.1524(7) _cell_length_c 12.3530(6) _cell_angle_alpha 66.270(5) _cell_angle_beta 77.808(4) _cell_angle_gamma 72.732(4) _cell_volume 959.05(8) _cell_formula_units_Z 1 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5458 _cell_measurement_theta_min 2.9130 _cell_measurement_theta_max 29.6317 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.81603 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET) (compiled Nov 25 2010,17:55:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0268 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12777 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _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 2.92 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4185 _reflns_number_gt 3635 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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. The asymmetric unit of the sterically hindered linker contains two crystallographically independent molecules. One is well ordered whereas the butyldicarboxamide linker in the second is disordered over two locations. ; _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^)+(0.0472P)^2^+0.4422P] 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 4185 _refine_ls_number_parameters 273 _refine_ls_number_restraints 79 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1153 _refine_ls_wR_factor_gt 0.1090 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.030 _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 O1 O 0.05646(15) 0.34448(9) 0.48986(9) 0.0360(3) Uani 1 1 d . . . N1 N 0.22417(18) 0.00341(11) 0.33193(10) 0.0324(3) Uani 1 1 d . . . N2 N 0.34081(17) 0.36890(11) 0.38076(10) 0.0278(3) Uani 1 1 d . . . N3 N 0.20620(19) 0.45298(13) 0.85236(11) 0.0391(3) Uani 1 1 d . A . C1 C 0.0584(2) 0.07972(14) 0.35143(13) 0.0350(3) Uani 1 1 d . . . H1 H -0.0567 0.0645 0.3435 0.042 Uiso 1 1 calc R . . C2 C 0.0445(2) 0.17944(13) 0.38238(12) 0.0301(3) Uani 1 1 d . . . H2 H -0.0768 0.2299 0.3973 0.036 Uiso 1 1 calc R . . C3 C 0.21305(19) 0.20383(11) 0.39102(11) 0.0241(3) Uani 1 1 d . . . C4 C 0.38620(19) 0.12627(12) 0.36921(11) 0.0253(3) Uani 1 1 d . . . H4 H 0.5035 0.1414 0.3737 0.030 Uiso 1 1 calc R . . C5 C 0.3873(2) 0.02605(12) 0.34065(11) 0.0274(3) Uani 1 1 d . . . C6 C 0.5715(2) -0.06082(14) 0.31819(14) 0.0375(3) Uani 1 1 d . . . H6A H 0.5436 -0.1250 0.2997 0.056 Uiso 0.50 1 calc PR . . H6B H 0.6402 -0.0995 0.3893 0.056 Uiso 0.50 1 calc PR . . H6C H 0.6511 -0.0147 0.2510 0.056 Uiso 0.50 1 calc PR . . H6D H 0.6797 -0.0345 0.3269 0.056 Uiso 0.50 1 calc PR . . H6E H 0.5831 -0.0599 0.2373 0.056 Uiso 0.50 1 calc PR . . H6F H 0.5722 -0.1448 0.3756 0.056 Uiso 0.50 1 calc PR . . C7 C 0.19788(19) 0.31215(12) 0.42547(11) 0.0253(3) Uani 1 1 d . . . C8 C 0.3478(2) 0.47597(12) 0.40474(13) 0.0309(3) Uani 1 1 d . . . H8A H 0.2191 0.5107 0.4380 0.037 Uiso 1 1 calc R . . H8B H 0.3821 0.5405 0.3291 0.037 Uiso 1 1 calc R . . C9 C 0.4923(2) 0.44291(12) 0.49130(12) 0.0293(3) Uani 1 1 d . . . H9A H 0.6194 0.4029 0.4608 0.035 Uiso 1 1 calc R . . H9B H 0.4530 0.3829 0.5690 0.035 Uiso 1 1 calc R . . C10 C 0.1120(2) 0.43617(14) 0.78068(13) 0.0361(3) Uani 1 1 d . . . H10 H 0.1250 0.4841 0.6981 0.043 Uiso 1 1 calc R . . C11 C -0.0028(2) 0.35318(14) 0.82006(13) 0.0330(3) Uani 1 1 d . A . H11 H -0.0643 0.3425 0.7658 0.040 Uiso 1 1 calc R . . C12 C -0.0260(2) 0.28561(14) 0.94122(13) 0.0332(3) Uani 1 1 d . . . C13 C 0.07153(19) 0.30210(13) 1.01567(12) 0.0303(3) Uani 1 1 d . A . H13 H 0.0577 0.2572 1.0989 0.036 Uiso 1 1 calc R . . C14 C 0.1893(2) 0.38413(14) 0.96872(13) 0.0330(3) Uani 1 1 d . . . C15 C 0.3041(3) 0.39941(19) 1.04682(16) 0.0511(5) Uani 1 1 d . A . H15A H 0.3784 0.4610 0.9984 0.077 Uiso 0.50 1 calc PR . . H15B H 0.3914 0.3200 1.0853 0.077 Uiso 0.50 1 calc PR . . H15C H 0.2172 0.4272 1.1077 0.077 Uiso 0.50 1 calc PR . . H15D H 0.2796 0.3445 1.1292 0.077 Uiso 0.50 1 calc PR . . H15E H 0.2666 0.4854 1.0423 0.077 Uiso 0.50 1 calc PR . . H15F H 0.4408 0.3783 1.0199 0.077 Uiso 0.50 1 calc PR . . O2 O -0.1857(3) 0.14677(17) 1.10953(16) 0.0338(4) Uani 0.6585(15) 1 d PU A 1 C18 C -0.4561(5) 0.0557(3) 0.9831(5) 0.0468(9) Uani 0.6585(15) 1 d PDU . 1 H18A H -0.4968 0.1173 0.9055 0.056 Uiso 0.6585(15) 1 calc PR A 1 H18B H -0.5077 0.0950 1.0431 0.056 Uiso 0.6585(15) 1 calc PR A 1 C16 C -0.1291(3) 0.1791(2) 1.0021(2) 0.0285(4) Uani 0.6585(15) 1 d PU A 1 C17 C -0.2428(4) 0.0233(2) 0.9750(2) 0.0425(5) Uani 0.6585(15) 1 d PDU A 1 H17A H -0.2029 -0.0311 1.0550 0.051 Uiso 0.6585(15) 1 calc PR A 1 H17B H -0.1918 -0.0246 0.9221 0.051 Uiso 0.6585(15) 1 calc PR A 1 N4 N -0.1566(3) 0.12884(18) 0.93087(18) 0.0389(4) Uani 0.6585(15) 1 d PU A 1 H4N H -0.117(4) 0.155(3) 0.856(3) 0.047 Uiso 0.66 1 d P A 1 C17B C -0.4500(8) 0.1614(4) 0.9471(4) 0.0425(5) Uani 0.3415(15) 1 d PDU A 2 H17C H -0.5341 0.2039 0.8821 0.051 Uiso 0.3415(15) 1 calc PR A 2 H17D H -0.5204 0.1813 1.0172 0.051 Uiso 0.3415(15) 1 calc PR A 2 N4B N -0.2779(6) 0.2092(4) 0.9103(3) 0.0389(4) Uani 0.3415(15) 1 d PDU A 2 H5N H -0.230(8) 0.217(5) 0.837(2) 0.047 Uiso 0.34 1 d PD A 2 O2B O -0.2548(6) 0.2023(3) 1.0923(3) 0.0338(4) Uani 0.3415(15) 1 d PU A 2 C16B C -0.2002(7) 0.2310(4) 0.9851(4) 0.0285(4) Uani 0.3415(15) 1 d PU A 2 C18B C -0.4095(9) 0.0243(7) 0.9780(12) 0.0468(9) Uani 0.3415(15) 1 d PDU . 2 H18C H -0.3205 -0.0183 1.0403 0.056 Uiso 0.3415(15) 1 calc PR A 2 H18D H -0.3455 0.0046 0.9068 0.056 Uiso 0.3415(15) 1 calc PR A 2 O1W O -0.33100(16) 0.32179(12) 1.23209(10) 0.0394(3) Uani 1 1 d . . . H1W H -0.284(3) 0.277(2) 1.1858(19) 0.059 Uiso 1 1 d . . . H2W H -0.295(3) 0.389(2) 1.2027(19) 0.059 Uiso 1 1 d . . . O2W O -0.1426(2) 0.20248(13) 0.68483(11) 0.0587(4) Uani 1 1 d . . . H3W H -0.174(4) 0.141(3) 0.678(2) 0.088 Uiso 1 1 d . . . H4W H -0.077(4) 0.240(3) 0.621(3) 0.088 Uiso 1 1 d . . . H1N H 0.434(3) 0.3453(16) 0.3322(16) 0.038(5) 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 0.0409(6) 0.0298(5) 0.0401(6) -0.0183(5) 0.0103(5) -0.0146(4) N1 0.0458(7) 0.0295(6) 0.0300(6) -0.0131(5) -0.0015(5) -0.0190(5) N2 0.0339(6) 0.0267(6) 0.0309(6) -0.0158(5) 0.0008(5) -0.0141(5) N3 0.0423(7) 0.0436(7) 0.0348(7) -0.0058(6) -0.0051(5) -0.0262(6) C1 0.0392(8) 0.0382(8) 0.0379(8) -0.0157(6) -0.0041(6) -0.0213(6) C2 0.0310(7) 0.0302(7) 0.0332(7) -0.0123(6) -0.0036(6) -0.0116(5) C3 0.0327(7) 0.0217(6) 0.0205(6) -0.0065(5) -0.0021(5) -0.0122(5) C4 0.0310(6) 0.0259(6) 0.0228(6) -0.0092(5) -0.0009(5) -0.0130(5) C5 0.0398(7) 0.0240(6) 0.0203(6) -0.0073(5) -0.0013(5) -0.0128(5) C6 0.0494(9) 0.0316(8) 0.0346(7) -0.0180(6) -0.0017(6) -0.0075(6) C7 0.0316(7) 0.0221(6) 0.0241(6) -0.0084(5) -0.0031(5) -0.0090(5) C8 0.0407(8) 0.0251(7) 0.0349(7) -0.0147(6) -0.0034(6) -0.0143(6) C9 0.0370(7) 0.0260(7) 0.0326(7) -0.0150(6) -0.0010(6) -0.0138(5) C10 0.0456(8) 0.0344(8) 0.0297(7) -0.0052(6) -0.0053(6) -0.0195(6) C11 0.0372(7) 0.0368(8) 0.0320(7) -0.0145(6) -0.0027(6) -0.0163(6) C12 0.0359(7) 0.0382(8) 0.0338(7) -0.0189(6) 0.0083(6) -0.0205(6) C13 0.0305(7) 0.0316(7) 0.0283(7) -0.0085(6) 0.0001(5) -0.0121(5) C14 0.0268(7) 0.0383(8) 0.0337(7) -0.0072(6) -0.0057(6) -0.0139(6) C15 0.0448(9) 0.0723(12) 0.0423(9) -0.0083(9) -0.0132(7) -0.0345(9) O2 0.0481(12) 0.0296(10) 0.0277(7) -0.0110(9) 0.0063(7) -0.0211(8) C18 0.083(2) 0.044(2) 0.0299(10) -0.0167(16) 0.0064(16) -0.0421(19) C16 0.0356(14) 0.0226(13) 0.0289(9) -0.0105(11) 0.0031(9) -0.0121(9) C17 0.0696(14) 0.0347(11) 0.0366(10) -0.0210(9) 0.0168(10) -0.0356(10) N4 0.0651(13) 0.0309(9) 0.0306(8) -0.0172(8) 0.0141(8) -0.0305(8) C17B 0.0696(14) 0.0347(11) 0.0366(10) -0.0210(9) 0.0168(10) -0.0356(10) N4B 0.0651(13) 0.0309(9) 0.0306(8) -0.0172(8) 0.0141(8) -0.0305(8) O2B 0.0481(12) 0.0296(10) 0.0277(7) -0.0110(9) 0.0063(7) -0.0211(8) C16B 0.0356(14) 0.0226(13) 0.0289(9) -0.0105(11) 0.0031(9) -0.0121(9) C18B 0.083(2) 0.044(2) 0.0299(10) -0.0167(16) 0.0064(16) -0.0421(19) O1W 0.0356(6) 0.0446(7) 0.0404(6) -0.0124(5) 0.0053(5) -0.0234(5) O2W 0.1123(12) 0.0518(8) 0.0346(6) -0.0238(6) 0.0179(7) -0.0577(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C7 1.2357(16) . ? N1 C1 1.337(2) . ? N1 C5 1.3408(18) . ? N2 C7 1.3275(17) . ? N2 C8 1.4626(16) . ? N2 H1N 0.871(18) . ? N3 C10 1.3391(19) . ? N3 C14 1.3416(19) . ? C1 C2 1.381(2) . ? C1 H1 0.9500 . ? C2 C3 1.3899(18) . ? C2 H2 0.9500 . ? C3 C4 1.3883(19) . ? C3 C7 1.5068(17) . ? C4 C5 1.3954(18) . ? C4 H4 0.9500 . ? C5 C6 1.501(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C6 H6D 0.9800 . ? C6 H6E 0.9800 . ? C6 H6F 0.9800 . ? C8 C9 1.521(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C9 1.526(2) 2_666 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.379(2) . ? C10 H10 0.9500 . ? C11 C12 1.389(2) . ? C11 H11 0.9500 . ? C12 C13 1.383(2) . ? C12 C16B 1.515(5) . ? C12 C16 1.541(3) . ? C13 C14 1.3837(19) . ? C13 H13 0.9500 . ? C14 C15 1.502(2) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C15 H15D 0.9800 . ? C15 H15E 0.9800 . ? C15 H15F 0.9800 . ? O2 C16 1.239(3) . ? C18 C17 1.490(4) . ? C18 C18 1.540(5) 2_457 ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C16 N4 1.329(3) . ? C17 N4 1.455(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? N4 H4N 0.86(3) . ? N4 H5N 1.31(5) . ? C17B N4B 1.457(6) . ? C17B C18B 1.501(7) . ? C17B H17C 0.9900 . ? C17B H17D 0.9900 . ? N4B C16B 1.326(6) . ? N4B H4N 1.35(3) . ? N4B H5N 0.877(10) . ? O2B C16B 1.234(6) . ? C18B C18B 1.521(9) 2_457 ? C18B H18C 0.9900 . ? C18B H18D 0.9900 . ? O1W H1W 0.89(2) . ? O1W H2W 0.85(2) . ? O2W H3W 0.88(3) . ? O2W H4W 0.86(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 118.25(12) . . ? C7 N2 C8 122.96(12) . . ? C7 N2 H1N 120.5(11) . . ? C8 N2 H1N 116.5(11) . . ? C10 N3 C14 118.01(12) . . ? N1 C1 C2 123.92(13) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C1 C2 C3 118.14(13) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C4 C3 C2 118.44(12) . . ? C4 C3 C7 123.42(12) . . ? C2 C3 C7 118.14(12) . . ? C3 C4 C5 119.75(12) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? N1 C5 C4 121.50(13) . . ? N1 C5 C6 117.26(12) . . ? C4 C5 C6 121.25(13) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C6 H6D 109.5 . . ? H6A C6 H6D 141.1 . . ? H6B C6 H6D 56.3 . . ? H6C C6 H6D 56.3 . . ? C5 C6 H6E 109.5 . . ? H6A C6 H6E 56.3 . . ? H6B C6 H6E 141.1 . . ? H6C C6 H6E 56.3 . . ? H6D C6 H6E 109.5 . . ? C5 C6 H6F 109.5 . . ? H6A C6 H6F 56.3 . . ? H6B C6 H6F 56.3 . . ? H6C C6 H6F 141.1 . . ? H6D C6 H6F 109.5 . . ? H6E C6 H6F 109.5 . . ? O1 C7 N2 124.08(12) . . ? O1 C7 C3 119.93(11) . . ? N2 C7 C3 115.98(11) . . ? N2 C8 C9 112.25(11) . . ? N2 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? N2 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C9 111.56(14) . 2_666 ? C8 C9 H9A 109.3 . . ? C9 C9 H9A 109.3 2_666 . ? C8 C9 H9B 109.3 . . ? C9 C9 H9B 109.3 2_666 . ? H9A C9 H9B 108.0 . . ? N3 C10 C11 123.66(14) . . ? N3 C10 H10 118.2 . . ? C11 C10 H10 118.2 . . ? C10 C11 C12 118.17(13) . . ? C10 C11 H11 120.9 . . ? C12 C11 H11 120.9 . . ? C13 C12 C11 118.46(13) . . ? C13 C12 C16B 122.9(2) . . ? C11 C12 C16B 115.8(2) . . ? C13 C12 C16 114.51(15) . . ? C11 C12 C16 126.49(15) . . ? C16B C12 C16 25.63(16) . . ? C12 C13 C14 119.87(13) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? N3 C14 C13 121.75(13) . . ? N3 C14 C15 117.29(13) . . ? C13 C14 C15 120.96(13) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C15 H15D 109.5 . . ? H15A C15 H15D 141.1 . . ? H15B C15 H15D 56.3 . . ? H15C C15 H15D 56.3 . . ? C14 C15 H15E 109.5 . . ? H15A C15 H15E 56.3 . . ? H15B C15 H15E 141.1 . . ? H15C C15 H15E 56.3 . . ? H15D C15 H15E 109.5 . . ? C14 C15 H15F 109.5 . . ? H15A C15 H15F 56.3 . . ? H15B C15 H15F 56.3 . . ? H15C C15 H15F 141.1 . . ? H15D C15 H15F 109.5 . . ? H15E C15 H15F 109.5 . . ? C17 C18 C18 114.0(4) . 2_457 ? C17 C18 H18A 108.7 . . ? C18 C18 H18A 108.7 2_457 . ? C17 C18 H18B 108.7 . . ? C18 C18 H18B 108.7 2_457 . ? H18A C18 H18B 107.6 . . ? O2 C16 N4 123.6(2) . . ? O2 C16 C12 120.91(19) . . ? N4 C16 C12 115.44(18) . . ? N4 C17 C18 114.7(2) . . ? N4 C17 H17A 108.6 . . ? C18 C17 H17A 108.6 . . ? N4 C17 H17B 108.6 . . ? C18 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C16 N4 C17 122.43(19) . . ? C16 N4 H4N 120.6(19) . . ? C17 N4 H4N 116.8(19) . . ? C16 N4 H5N 109(2) . . ? C17 N4 H5N 113(2) . . ? H4N N4 H5N 46(2) . . ? N4B C17B C18B 113.5(4) . . ? N4B C17B H17C 108.9 . . ? C18B C17B H17C 108.9 . . ? N4B C17B H17D 108.9 . . ? C18B C17B H17D 108.9 . . ? H17C C17B H17D 107.7 . . ? C16B N4B C17B 121.6(4) . . ? C16B N4B H4N 99.7(13) . . ? C17B N4B H4N 122.1(13) . . ? C16B N4B H5N 125(4) . . ? C17B N4B H5N 113(4) . . ? H4N N4B H5N 43(4) . . ? O2B C16B N4B 123.5(4) . . ? O2B C16B C12 116.7(4) . . ? N4B C16B C12 119.6(4) . . ? C17B C18B C18B 112.5(8) . 2_457 ? C17B C18B H18C 109.1 . . ? C18B C18B H18C 109.1 2_457 . ? C17B C18B H18D 109.1 . . ? C18B C18B H18D 109.1 2_457 . ? H18C C18B H18D 107.8 . . ? H1W O1W H2W 111(2) . . ? H3W O2W H4W 111(2) . . ? 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 C5 N1 C1 C2 -1.3(2) . . . . ? N1 C1 C2 C3 1.6(2) . . . . ? C1 C2 C3 C4 -0.57(19) . . . . ? C1 C2 C3 C7 -179.65(12) . . . . ? C2 C3 C4 C5 -0.64(19) . . . . ? C7 C3 C4 C5 178.39(11) . . . . ? C1 N1 C5 C4 0.0(2) . . . . ? C1 N1 C5 C6 -179.91(13) . . . . ? C3 C4 C5 N1 0.98(19) . . . . ? C3 C4 C5 C6 -179.13(12) . . . . ? C8 N2 C7 O1 1.0(2) . . . . ? C8 N2 C7 C3 179.62(12) . . . . ? C4 C3 C7 O1 -149.36(13) . . . . ? C2 C3 C7 O1 29.67(18) . . . . ? C4 C3 C7 N2 31.96(18) . . . . ? C2 C3 C7 N2 -149.01(13) . . . . ? C7 N2 C8 C9 105.66(15) . . . . ? N2 C8 C9 C9 176.06(14) . . . 2_666 ? C14 N3 C10 C11 0.8(2) . . . . ? N3 C10 C11 C12 1.7(2) . . . . ? C10 C11 C12 C13 -1.9(2) . . . . ? C10 C11 C12 C16B 159.6(2) . . . . ? C10 C11 C12 C16 -172.96(17) . . . . ? C11 C12 C13 C14 -0.2(2) . . . . ? C16B C12 C13 C14 -160.4(2) . . . . ? C16 C12 C13 C14 171.84(15) . . . . ? C10 N3 C14 C13 -3.1(2) . . . . ? C10 N3 C14 C15 176.87(15) . . . . ? C12 C13 C14 N3 2.9(2) . . . . ? C12 C13 C14 C15 -177.11(15) . . . . ? C13 C12 C16 O2 27.8(3) . . . . ? C11 C12 C16 O2 -160.9(2) . . . . ? C16B C12 C16 O2 -87.7(5) . . . . ? C13 C12 C16 N4 -154.19(19) . . . . ? C11 C12 C16 N4 17.1(3) . . . . ? C16B C12 C16 N4 90.4(6) . . . . ? C18 C18 C17 N4 173.7(5) 2_457 . . . ? O2 C16 N4 C17 -5.3(4) . . . . ? C12 C16 N4 C17 176.8(2) . . . . ? C18 C17 N4 C16 87.3(4) . . . . ? C18B C17B N4B C16B -98.8(7) . . . . ? C17B N4B C16B O2B 7.1(7) . . . . ? C17B N4B C16B C12 -177.5(4) . . . . ? C13 C12 C16B O2B 0.8(5) . . . . ? C11 C12 C16B O2B -159.9(3) . . . . ? C16 C12 C16B O2B 78.9(6) . . . . ? C13 C12 C16B N4B -174.9(3) . . . . ? C11 C12 C16B N4B 24.4(5) . . . . ? C16 C12 C16B N4B -96.8(6) . . . . ? N4B C17B C18B C18B 177.1(11) . . . 2_457 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.301 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.040