# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name U.Bunz K.I.Hardcastle D.Schweinfurth _publ_contact_author_name 'Prof. Uwe Bunz' _publ_contact_author_email UB7@MAIL.GATECH.EDU data_ds_2s _database_code_depnum_ccdc_archive 'CCDC 673443' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 N4 O' _chemical_formula_sum 'C17 H18 N4 O' _chemical_formula_weight 294.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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) _chemical_absolute_configuration AD loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.6887(6) _cell_length_b 7.2477(4) _cell_length_c 17.9172(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.701(2) _cell_angle_gamma 90.00 _cell_volume 1514.71(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5400 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 64.38 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.670 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7755 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details 'SADABS V2.10, Sheldrick 2003' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8665 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 64.58 _reflns_number_total 3519 _reflns_number_gt 3404 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0500P)^2^+0.1000P] 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 0.11(19) _refine_ls_number_reflns 3519 _refine_ls_number_parameters 399 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0272 _refine_ls_wR_factor_ref 0.0742 _refine_ls_wR_factor_gt 0.0733 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.83466(14) -0.3445(3) -0.55384(8) 0.0408(4) Uani 1 1 d . . . H1 H -0.7593 -0.3534 -0.5309 0.049 Uiso 1 1 calc R . . C2 C -0.92222(15) -0.3050(3) -0.50884(9) 0.0440(4) Uani 1 1 d . . . H2 H -0.9073 -0.2848 -0.4567 0.053 Uiso 1 1 calc R . . C3 C -1.03214(14) -0.2956(3) -0.54111(8) 0.0432(4) Uani 1 1 d . . . H3 H -1.0948 -0.2693 -0.5116 0.052 Uiso 1 1 calc R . . C4 C -1.04981(13) -0.3247(3) -0.61684(8) 0.0371(4) Uani 1 1 d . . . H4 H -1.1251 -0.3210 -0.6402 0.044 Uiso 1 1 calc R . . C5 C -0.95603(13) -0.3598(2) -0.65875(8) 0.0293(3) Uani 1 1 d . . . C6 C -0.96999(12) -0.3767(2) -0.74043(8) 0.0279(3) Uani 1 1 d . . . C7 C -0.88841(13) -0.3784(2) -0.79245(8) 0.0279(3) Uani 1 1 d . . . H7 H -0.8074 -0.3786 -0.7835 0.033 Uiso 1 1 calc R . . C8 C -0.91145(12) -0.3666(2) -0.93359(7) 0.0259(3) Uani 1 1 d . . . C9 C -0.80718(12) -0.2832(2) -0.94583(8) 0.0279(3) Uani 1 1 d . . . H9 H -0.7593 -0.2382 -0.9050 0.033 Uiso 1 1 calc R . . C10 C -0.77412(13) -0.2666(2) -1.01793(8) 0.0293(4) Uani 1 1 d . . . H10 H -0.7025 -0.2114 -1.0268 0.035 Uiso 1 1 calc R . . C11 C -0.84502(13) -0.3303(2) -1.07806(8) 0.0281(4) Uani 1 1 d . . . C12 C -0.94916(14) -0.4114(2) -1.06526(8) 0.0305(4) Uani 1 1 d . . . H12 H -0.9979 -0.4539 -1.1062 0.037 Uiso 1 1 calc R . . C13 C -0.98250(14) -0.4308(2) -0.99243(8) 0.0288(4) Uani 1 1 d . . . H13 H -1.0535 -0.4877 -0.9833 0.035 Uiso 1 1 calc R . . C14 C -0.87575(14) -0.3637(3) -1.21072(8) 0.0353(4) Uani 1 1 d . . . H14A H -0.9452 -0.2854 -1.2153 0.042 Uiso 1 1 calc R . . H14B H -0.8999 -0.4936 -1.2051 0.042 Uiso 1 1 calc R . . C15 C -0.80817(14) -0.3430(3) -1.27924(8) 0.0371(4) Uani 1 1 d . . . H15A H -0.7843 -0.2126 -1.2837 0.045 Uiso 1 1 calc R . . H15B H -0.8583 -0.3738 -1.3241 0.045 Uiso 1 1 calc R . . C16 C -0.70293(16) -0.4645(3) -1.27741(9) 0.0438(4) Uani 1 1 d . . . H16A H -0.7260 -0.5931 -1.2673 0.053 Uiso 1 1 calc R . . H16B H -0.6492 -0.4246 -1.2355 0.053 Uiso 1 1 calc R . . C17 C -0.64070(18) -0.4609(3) -1.34926(10) 0.0518(5) Uani 1 1 d . . . H17A H -0.6198 -0.3336 -1.3607 0.078 Uiso 1 1 calc R . . H17B H -0.6910 -0.5105 -1.3903 0.078 Uiso 1 1 calc R . . H17C H -0.5712 -0.5364 -1.3431 0.078 Uiso 1 1 calc R . . N1 N -0.84819(11) -0.3711(2) -0.62758(7) 0.0352(3) Uani 1 1 d . . . N2 N -1.07552(11) -0.3791(2) -0.77715(7) 0.0339(3) Uani 1 1 d . . . N3 N -1.06356(11) -0.3806(2) -0.84917(7) 0.0340(3) Uani 1 1 d . . . N4 N -0.94929(10) -0.37956(19) -0.85902(6) 0.0273(3) Uani 1 1 d . . . O1 O -0.80314(9) -0.30788(17) -1.14699(5) 0.0351(3) Uani 1 1 d . . . C1B C -0.32293(14) -0.4880(3) -0.55470(8) 0.0392(4) Uani 1 1 d . . . H1B H -0.2459 -0.4947 -0.5344 0.047 Uiso 1 1 calc R . . C2B C -0.40898(14) -0.5153(3) -0.50685(8) 0.0411(4) Uani 1 1 d . . . H2B H -0.3918 -0.5414 -0.4554 0.049 Uiso 1 1 calc R . . C3B C -0.52075(14) -0.5037(3) -0.53608(8) 0.0421(4) Uani 1 1 d . . . H3B H -0.5824 -0.5222 -0.5048 0.050 Uiso 1 1 calc R . . C4B C -0.54246(14) -0.4651(3) -0.61073(8) 0.0354(4) Uani 1 1 d . . . H4B H -0.6190 -0.4540 -0.6316 0.042 Uiso 1 1 calc R . . C5B C -0.45026(13) -0.4426(2) -0.65514(8) 0.0289(4) Uani 1 1 d . . . C6B C -0.46736(13) -0.4094(2) -0.73600(8) 0.0280(4) Uani 1 1 d . . . C7B C -0.38880(14) -0.4120(2) -0.78969(8) 0.0292(4) Uani 1 1 d . . . H7B H -0.3087 -0.4338 -0.7830 0.035 Uiso 1 1 calc R . . C8B C -0.41427(12) -0.3604(2) -0.92859(8) 0.0267(3) Uani 1 1 d . . . C9B C -0.30862(13) -0.2808(2) -0.93996(8) 0.0288(3) Uani 1 1 d . . . H9B H -0.2611 -0.2370 -0.8987 0.035 Uiso 1 1 calc R . . C10B C -0.27358(13) -0.2663(2) -1.01175(8) 0.0300(4) Uani 1 1 d . . . H10B H -0.2011 -0.2134 -1.0200 0.036 Uiso 1 1 calc R . . C11B C -0.34411(13) -0.3287(2) -1.07231(8) 0.0296(4) Uani 1 1 d . . . C12B C -0.44989(14) -0.4060(2) -1.06048(8) 0.0310(4) Uani 1 1 d . . . H12B H -0.4985 -0.4471 -1.1017 0.037 Uiso 1 1 calc R . . C13B C -0.48419(14) -0.4229(2) -0.98823(8) 0.0290(4) Uani 1 1 d . . . H13B H -0.5560 -0.4776 -0.9797 0.035 Uiso 1 1 calc R . . C14B C -0.37471(14) -0.3516(3) -1.20550(8) 0.0355(4) Uani 1 1 d . . . H14C H -0.4452 -0.2758 -1.2058 0.043 Uiso 1 1 calc R . . H14D H -0.3968 -0.4834 -1.2050 0.043 Uiso 1 1 calc R . . C15B C -0.30992(14) -0.3098(2) -1.27371(8) 0.0368(4) Uani 1 1 d . . . H15C H -0.3632 -0.3210 -1.3187 0.044 Uiso 1 1 calc R . . H15D H -0.2828 -0.1805 -1.2707 0.044 Uiso 1 1 calc R . . C16B C -0.20834(16) -0.4344(3) -1.28276(10) 0.0439(5) Uani 1 1 d . . . H16C H -0.2353 -0.5635 -1.2882 0.053 Uiso 1 1 calc R . . H16D H -0.1560 -0.4272 -1.2372 0.053 Uiso 1 1 calc R . . C17B C -0.14255(16) -0.3822(3) -1.35068(9) 0.0470(5) Uani 1 1 d . . . H17D H -0.1124 -0.2566 -1.3444 0.071 Uiso 1 1 calc R . . H17E H -0.1942 -0.3881 -1.3959 0.071 Uiso 1 1 calc R . . H17F H -0.0788 -0.4685 -1.3553 0.071 Uiso 1 1 calc R . . N1B N -0.34034(11) -0.4527(2) -0.62768(7) 0.0339(3) Uani 1 1 d . . . N2B N -0.57284(11) -0.3741(2) -0.76950(7) 0.0335(3) Uani 1 1 d . . . N3B N -0.56340(11) -0.3534(2) -0.84159(7) 0.0338(3) Uani 1 1 d . . . N4B N -0.45099(10) -0.37649(19) -0.85415(6) 0.0280(3) Uani 1 1 d . . . O1B O -0.30025(9) -0.30882(18) -1.14068(5) 0.0366(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0397(10) 0.0498(11) 0.0318(9) 0.0010(8) -0.0046(7) -0.0018(9) C2 0.0526(12) 0.0525(12) 0.0271(8) -0.0015(8) 0.0041(7) -0.0098(9) C3 0.0425(11) 0.0533(11) 0.0353(9) -0.0027(8) 0.0150(7) -0.0108(9) C4 0.0342(10) 0.0424(11) 0.0350(8) -0.0013(7) 0.0057(6) -0.0043(7) C5 0.0328(9) 0.0277(8) 0.0279(7) 0.0017(7) 0.0045(6) -0.0033(7) C6 0.0279(9) 0.0264(8) 0.0292(8) 0.0005(7) 0.0010(6) 0.0009(7) C7 0.0263(9) 0.0296(8) 0.0274(7) 0.0001(7) -0.0007(6) 0.0011(7) C8 0.0254(9) 0.0247(8) 0.0277(7) 0.0007(6) 0.0009(6) 0.0017(7) C9 0.0252(9) 0.0280(8) 0.0299(8) -0.0012(7) -0.0026(6) 0.0014(7) C10 0.0249(9) 0.0286(9) 0.0346(8) 0.0009(6) 0.0029(6) -0.0004(6) C11 0.0287(9) 0.0288(9) 0.0269(7) 0.0009(6) 0.0030(6) 0.0033(7) C12 0.0301(10) 0.0315(10) 0.0293(8) -0.0040(6) -0.0011(6) -0.0020(7) C13 0.0249(9) 0.0292(9) 0.0323(8) -0.0009(6) 0.0030(6) -0.0019(6) C14 0.0370(10) 0.0397(10) 0.0290(8) -0.0026(7) 0.0005(6) -0.0031(8) C15 0.0447(10) 0.0399(11) 0.0268(7) 0.0004(7) 0.0021(6) -0.0012(8) C16 0.0519(12) 0.0438(11) 0.0367(9) 0.0027(8) 0.0108(7) 0.0052(9) C17 0.0663(14) 0.0430(11) 0.0487(11) 0.0023(9) 0.0240(9) 0.0044(10) N1 0.0349(8) 0.0395(8) 0.0310(7) 0.0001(6) 0.0001(5) -0.0003(6) N2 0.0328(8) 0.0405(8) 0.0286(7) -0.0004(6) 0.0041(5) -0.0004(7) N3 0.0232(8) 0.0449(9) 0.0340(7) -0.0007(6) 0.0028(5) -0.0003(6) N4 0.0247(8) 0.0289(7) 0.0280(6) 0.0003(6) 0.0012(5) 0.0009(6) O1 0.0358(7) 0.0437(7) 0.0263(5) -0.0027(5) 0.0049(4) -0.0057(5) C1B 0.0361(10) 0.0444(11) 0.0363(9) 0.0018(8) -0.0039(7) -0.0023(8) C2B 0.0479(11) 0.0475(11) 0.0277(8) 0.0001(7) 0.0017(7) 0.0014(9) C3B 0.0403(10) 0.0539(11) 0.0331(9) -0.0008(8) 0.0105(7) -0.0008(9) C4B 0.0314(9) 0.0416(10) 0.0335(8) -0.0036(7) 0.0046(6) -0.0008(8) C5B 0.0305(10) 0.0253(8) 0.0311(8) -0.0017(6) 0.0046(6) -0.0006(7) C6B 0.0281(9) 0.0264(9) 0.0295(8) -0.0005(6) 0.0004(6) -0.0016(6) C7B 0.0261(9) 0.0302(10) 0.0310(8) 0.0008(6) -0.0007(6) 0.0008(6) C8B 0.0243(9) 0.0258(8) 0.0299(7) 0.0014(7) 0.0022(6) 0.0015(7) C9B 0.0251(9) 0.0284(8) 0.0323(8) 0.0002(7) -0.0020(6) 0.0010(7) C10B 0.0239(9) 0.0289(9) 0.0373(9) 0.0027(7) 0.0036(6) -0.0010(6) C11B 0.0286(9) 0.0283(9) 0.0321(8) 0.0018(6) 0.0046(6) 0.0030(7) C12B 0.0308(10) 0.0309(10) 0.0308(8) -0.0031(7) -0.0018(6) -0.0011(7) C13B 0.0245(9) 0.0277(9) 0.0348(8) 0.0008(6) 0.0023(6) -0.0016(6) C14B 0.0370(10) 0.0377(10) 0.0314(8) -0.0015(7) -0.0002(6) -0.0002(8) C15B 0.0440(10) 0.0349(10) 0.0313(8) 0.0010(7) 0.0007(7) 0.0022(7) C16B 0.0508(12) 0.0392(10) 0.0427(10) 0.0045(8) 0.0106(8) 0.0061(8) C17B 0.0514(12) 0.0467(11) 0.0446(10) -0.0024(8) 0.0161(8) -0.0017(9) N1B 0.0322(8) 0.0376(8) 0.0319(7) 0.0032(6) 0.0016(5) -0.0015(6) N2B 0.0296(8) 0.0386(8) 0.0328(7) 0.0026(6) 0.0052(5) 0.0018(6) N3B 0.0234(8) 0.0426(9) 0.0355(7) 0.0049(6) 0.0042(5) 0.0019(6) N4B 0.0252(8) 0.0296(7) 0.0293(7) 0.0018(6) 0.0017(5) 0.0007(6) O1B 0.0351(7) 0.0467(8) 0.0286(5) 0.0000(5) 0.0060(4) -0.0045(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.3344(19) . ? C1 C2 1.373(2) . ? C1 H1 0.9500 . ? C2 C3 1.376(2) . ? C2 H2 0.9500 . ? C3 C4 1.376(2) . ? C3 H3 0.9500 . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C5 N1 1.3480(19) . ? C5 C6 1.467(2) . ? C6 N2 1.3601(19) . ? C6 C7 1.376(2) . ? C7 N4 1.3489(19) . ? C7 H7 0.9500 . ? C8 C13 1.380(2) . ? C8 C9 1.390(2) . ? C8 N4 1.4373(17) . ? C9 C10 1.3773(19) . ? C9 H9 0.9500 . ? C10 C11 1.395(2) . ? C10 H10 0.9500 . ? C11 O1 1.3672(16) . ? C11 C12 1.384(2) . ? C12 C13 1.393(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O1 1.4363(18) . ? C14 C15 1.509(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.512(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.519(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N2 N3 1.3069(17) . ? N3 N4 1.3585(18) . ? C1B N1B 1.335(2) . ? C1B C2B 1.377(2) . ? C1B H1B 0.9500 . ? C2B C3B 1.378(2) . ? C2B H2B 0.9500 . ? C3B C4B 1.374(2) . ? C3B H3B 0.9500 . ? C4B C5B 1.390(2) . ? C4B H4B 0.9500 . ? C5B N1B 1.348(2) . ? C5B C6B 1.469(2) . ? C6B N2B 1.360(2) . ? C6B C7B 1.372(2) . ? C7B N4B 1.3491(19) . ? C7B H7B 0.9500 . ? C8B C13B 1.379(2) . ? C8B C9B 1.390(2) . ? C8B N4B 1.4320(18) . ? C9B C10B 1.379(2) . ? C9B H9B 0.9500 . ? C10B C11B 1.395(2) . ? C10B H10B 0.9500 . ? C11B O1B 1.3657(17) . ? C11B C12B 1.386(2) . ? C12B C13B 1.385(2) . ? C12B H12B 0.9500 . ? C13B H13B 0.9500 . ? C14B O1B 1.4395(18) . ? C14B C15B 1.509(2) . ? C14B H14C 0.9900 . ? C14B H14D 0.9900 . ? C15B C16B 1.509(2) . ? C15B H15C 0.9900 . ? C15B H15D 0.9900 . ? C16B C17B 1.528(2) . ? C16B H16C 0.9900 . ? C16B H16D 0.9900 . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? N2B N3B 1.3120(17) . ? N3B N4B 1.3576(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 124.49(15) . . ? N1 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C1 C2 C3 118.34(15) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 118.91(16) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 119.14(15) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 122.39(14) . . ? N1 C5 C6 116.68(13) . . ? C4 C5 C6 120.85(13) . . ? N2 C6 C7 108.59(12) . . ? N2 C6 C5 121.50(13) . . ? C7 C6 C5 129.73(14) . . ? N4 C7 C6 104.47(12) . . ? N4 C7 H7 127.8 . . ? C6 C7 H7 127.8 . . ? C13 C8 C9 121.09(14) . . ? C13 C8 N4 118.81(13) . . ? C9 C8 N4 120.04(13) . . ? C10 C9 C8 119.19(13) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 120.46(14) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? O1 C11 C12 124.77(13) . . ? O1 C11 C10 115.39(13) . . ? C12 C11 C10 119.84(13) . . ? C11 C12 C13 120.02(14) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C8 C13 C12 119.39(15) . . ? C8 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? O1 C14 C15 107.77(13) . . ? O1 C14 H14A 110.2 . . ? C15 C14 H14A 110.2 . . ? O1 C14 H14B 110.2 . . ? C15 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? C14 C15 C16 113.10(14) . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15B 109.0 . . ? C16 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C15 C16 C17 113.89(15) . . ? C15 C16 H16A 108.8 . . ? C17 C16 H16A 108.8 . . ? C15 C16 H16B 108.8 . . ? C17 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C1 N1 C5 116.69(14) . . ? N3 N2 C6 109.04(12) . . ? N2 N3 N4 107.28(11) . . ? C7 N4 N3 110.61(12) . . ? C7 N4 C8 130.17(13) . . ? N3 N4 C8 119.03(11) . . ? C11 O1 C14 117.19(12) . . ? N1B C1B C2B 124.47(15) . . ? N1B C1B H1B 117.8 . . ? C2B C1B H1B 117.8 . . ? C1B C2B C3B 117.83(14) . . ? C1B C2B H2B 121.1 . . ? C3B C2B H2B 121.1 . . ? C4B C3B C2B 119.57(15) . . ? C4B C3B H3B 120.2 . . ? C2B C3B H3B 120.2 . . ? C3B C4B C5B 118.68(15) . . ? C3B C4B H4B 120.7 . . ? C5B C4B H4B 120.7 . . ? N1B C5B C4B 122.73(14) . . ? N1B C5B C6B 115.76(13) . . ? C4B C5B C6B 121.50(14) . . ? N2B C6B C7B 108.76(13) . . ? N2B C6B C5B 121.84(14) . . ? C7B C6B C5B 129.38(14) . . ? N4B C7B C6B 104.46(13) . . ? N4B C7B H7B 127.8 . . ? C6B C7B H7B 127.8 . . ? C13B C8B C9B 120.69(14) . . ? C13B C8B N4B 119.78(14) . . ? C9B C8B N4B 119.53(13) . . ? C10B C9B C8B 119.26(14) . . ? C10B C9B H9B 120.4 . . ? C8B C9B H9B 120.4 . . ? C9B C10B C11B 120.29(14) . . ? C9B C10B H10B 119.9 . . ? C11B C10B H10B 119.9 . . ? O1B C11B C12B 124.75(13) . . ? O1B C11B C10B 115.22(13) . . ? C12B C11B C10B 120.02(13) . . ? C13B C12B C11B 119.58(14) . . ? C13B C12B H12B 120.2 . . ? C11B C12B H12B 120.2 . . ? C8B C13B C12B 120.15(15) . . ? C8B C13B H13B 119.9 . . ? C12B C13B H13B 119.9 . . ? O1B C14B C15B 107.54(13) . . ? O1B C14B H14C 110.2 . . ? C15B C14B H14C 110.2 . . ? O1B C14B H14D 110.2 . . ? C15B C14B H14D 110.2 . . ? H14C C14B H14D 108.5 . . ? C16B C15B C14B 114.00(14) . . ? C16B C15B H15C 108.8 . . ? C14B C15B H15C 108.8 . . ? C16B C15B H15D 108.8 . . ? C14B C15B H15D 108.8 . . ? H15C C15B H15D 107.6 . . ? C15B C16B C17B 112.18(15) . . ? C15B C16B H16C 109.2 . . ? C17B C16B H16C 109.2 . . ? C15B C16B H16D 109.2 . . ? C17B C16B H16D 109.2 . . ? H16C C16B H16D 107.9 . . ? C16B C17B H17D 109.5 . . ? C16B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? C16B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C1B N1B C5B 116.71(13) . . ? N3B N2B C6B 108.93(12) . . ? N2B N3B N4B 107.03(11) . . ? C7B N4B N3B 110.82(12) . . ? C7B N4B C8B 129.45(13) . . ? N3B N4B C8B 119.73(11) . . ? C11B O1B C14B 117.29(12) . . ? 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 N1 C1 C2 C3 1.3(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 -1.1(3) . . . . ? C3 C4 C5 N1 1.8(3) . . . . ? C3 C4 C5 C6 -175.00(17) . . . . ? N1 C5 C6 N2 175.75(15) . . . . ? C4 C5 C6 N2 -7.3(2) . . . . ? N1 C5 C6 C7 -9.7(3) . . . . ? C4 C5 C6 C7 167.24(18) . . . . ? N2 C6 C7 N4 0.7(2) . . . . ? C5 C6 C7 N4 -174.41(15) . . . . ? C13 C8 C9 C10 -0.7(2) . . . . ? N4 C8 C9 C10 -177.88(14) . . . . ? C8 C9 C10 C11 0.9(2) . . . . ? C9 C10 C11 O1 -179.55(14) . . . . ? C9 C10 C11 C12 -0.2(2) . . . . ? O1 C11 C12 C13 178.65(14) . . . . ? C10 C11 C12 C13 -0.6(2) . . . . ? C9 C8 C13 C12 -0.1(2) . . . . ? N4 C8 C13 C12 177.09(14) . . . . ? C11 C12 C13 C8 0.8(2) . . . . ? O1 C14 C15 C16 62.0(2) . . . . ? C14 C15 C16 C17 173.91(16) . . . . ? C2 C1 N1 C5 -0.7(3) . . . . ? C4 C5 N1 C1 -0.9(2) . . . . ? C6 C5 N1 C1 176.01(15) . . . . ? C7 C6 N2 N3 -0.5(2) . . . . ? C5 C6 N2 N3 175.08(15) . . . . ? C6 N2 N3 N4 0.08(18) . . . . ? C6 C7 N4 N3 -0.63(19) . . . . ? C6 C7 N4 C8 174.36(15) . . . . ? N2 N3 N4 C7 0.35(18) . . . . ? N2 N3 N4 C8 -175.27(14) . . . . ? C13 C8 N4 C7 158.71(17) . . . . ? C9 C8 N4 C7 -24.1(3) . . . . ? C13 C8 N4 N3 -26.7(2) . . . . ? C9 C8 N4 N3 150.57(15) . . . . ? C12 C11 O1 C14 3.6(2) . . . . ? C10 C11 O1 C14 -177.16(15) . . . . ? C15 C14 O1 C11 -174.83(14) . . . . ? N1B C1B C2B C3B -0.7(3) . . . . ? C1B C2B C3B C4B -0.2(3) . . . . ? C2B C3B C4B C5B 1.3(3) . . . . ? C3B C4B C5B N1B -1.6(2) . . . . ? C3B C4B C5B C6B 177.22(16) . . . . ? N1B C5B C6B N2B -171.92(15) . . . . ? C4B C5B C6B N2B 9.2(2) . . . . ? N1B C5B C6B C7B 9.9(2) . . . . ? C4B C5B C6B C7B -168.99(17) . . . . ? N2B C6B C7B N4B 0.34(18) . . . . ? C5B C6B C7B N4B 178.69(15) . . . . ? C13B C8B C9B C10B -0.6(2) . . . . ? N4B C8B C9B C10B 179.81(13) . . . . ? C8B C9B C10B C11B 0.8(2) . . . . ? C9B C10B C11B O1B -179.44(14) . . . . ? C9B C10B C11B C12B -0.1(2) . . . . ? O1B C11B C12B C13B 178.46(14) . . . . ? C10B C11B C12B C13B -0.9(2) . . . . ? C9B C8B C13B C12B -0.3(2) . . . . ? N4B C8B C13B C12B 179.27(14) . . . . ? C11B C12B C13B C8B 1.1(2) . . . . ? O1B C14B C15B C16B 66.6(2) . . . . ? C14B C15B C16B C17B -177.68(15) . . . . ? C2B C1B N1B C5B 0.4(3) . . . . ? C4B C5B N1B C1B 0.7(2) . . . . ? C6B C5B N1B C1B -178.16(15) . . . . ? C7B C6B N2B N3B -0.38(19) . . . . ? C5B C6B N2B N3B -178.87(14) . . . . ? C6B N2B N3B N4B 0.25(18) . . . . ? C6B C7B N4B N3B -0.19(17) . . . . ? C6B C7B N4B C8B 179.33(15) . . . . ? N2B N3B N4B C7B -0.04(17) . . . . ? N2B N3B N4B C8B -179.61(14) . . . . ? C13B C8B N4B C7B 144.38(17) . . . . ? C9B C8B N4B C7B -36.0(3) . . . . ? C13B C8B N4B N3B -36.1(2) . . . . ? C9B C8B N4B N3B 143.47(16) . . . . ? C12B C11B O1B C14B 7.5(2) . . . . ? C10B C11B O1B C14B -173.11(15) . . . . ? C15B C14B O1B C11B 177.07(13) . . . . ? _diffrn_measured_fraction_theta_max 0.875 _diffrn_reflns_theta_full 64.58 _diffrn_measured_fraction_theta_full 0.874 _refine_diff_density_max 0.084 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.033