# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H34 N10 O2' _chemical_formula_weight 746.82 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 11.751(3) _cell_length_b 12.885(3) _cell_length_c 13.632(3) _cell_angle_alpha 114.123(3) _cell_angle_beta 100.136(4) _cell_angle_gamma 97.330(4) _cell_volume 1808.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3819 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.07 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9739 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.874562 ; _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 '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 15267 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.25 _reflns_number_total 7879 _reflns_number_gt 5606 _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. Hydrogen atoms were assigned ideal positions on the carbon and oxygen atoms and refined isotropically as riding atoms. ; _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^)+(0.1068P)^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_extinction_coef ? _refine_ls_number_reflns 7879 _refine_ls_number_parameters 526 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0889 _refine_ls_R_factor_gt 0.0639 _refine_ls_wR_factor_ref 0.1871 _refine_ls_wR_factor_gt 0.1693 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 C1 C 0.20414(17) 1.09309(17) 1.12847(16) 0.0255(4) Uani 1 1 d . . . C2 C 0.12271(17) 1.10974(17) 1.20227(16) 0.0268(4) Uani 1 1 d . . . C3 C 0.11724(19) 1.20123(18) 1.29975(17) 0.0313(5) Uani 1 1 d . . . H3 H 0.1763 1.2717 1.3347 0.038 Uiso 1 1 calc R . . C4 C 0.02239(19) 1.18618(19) 1.34454(17) 0.0339(5) Uani 1 1 d . . . H4 H 0.0174 1.2466 1.4121 0.041 Uiso 1 1 calc R . . C5 C -0.06601(19) 1.08309(19) 1.29139(17) 0.0329(5) Uani 1 1 d . . . H5 H -0.1308 1.0752 1.3228 0.039 Uiso 1 1 calc R . . C6 C -0.06029(18) 0.99232(18) 1.19356(17) 0.0308(5) Uani 1 1 d . . . H6 H -0.1211 0.9232 1.1567 0.037 Uiso 1 1 calc R . . C7 C 0.03663(17) 1.00526(17) 1.15099(16) 0.0270(4) Uani 1 1 d . . . C8 C 0.07296(17) 0.92840(17) 1.05353(16) 0.0266(4) Uani 1 1 d . . . C9 C 0.04063(17) 0.74953(17) 0.89455(16) 0.0273(4) Uani 1 1 d . . . C10 C -0.03063(18) 0.63918(17) 0.81711(17) 0.0298(4) Uani 1 1 d . . . C11 C -0.14139(19) 0.5788(2) 0.8099(2) 0.0386(5) Uani 1 1 d . . . H11 H -0.1827 0.6096 0.8656 0.046 Uiso 1 1 calc R . . C12 C -0.1890(2) 0.4717(2) 0.7181(2) 0.0429(6) Uani 1 1 d . . . H12 H -0.2643 0.4286 0.7112 0.051 Uiso 1 1 calc R . . C13 C -0.1280(2) 0.4249(2) 0.6342(2) 0.0431(6) Uani 1 1 d . . . H13 H -0.1634 0.3513 0.5727 0.052 Uiso 1 1 calc R . . C14 C -0.01907(19) 0.48382(19) 0.64013(19) 0.0386(5) Uani 1 1 d . . . H14 H 0.0207 0.4521 0.5833 0.046 Uiso 1 1 calc R . . C15 C 0.03164(18) 0.59142(18) 0.73170(18) 0.0342(5) Uani 1 1 d . . . C16 C 0.13741(17) 0.67422(17) 0.75896(17) 0.0289(4) Uani 1 1 d . . . C17 C 0.30751(17) 0.74224(17) 0.71485(16) 0.0279(4) Uani 1 1 d . . . C18 C 0.39188(17) 0.72379(17) 0.64493(16) 0.0271(4) Uani 1 1 d . . . C19 C 0.40049(19) 0.62743(18) 0.55246(17) 0.0322(5) Uani 1 1 d . . . H19 H 0.3445 0.5553 0.5226 0.039 Uiso 1 1 calc R . . C20 C 0.49355(19) 0.64040(19) 0.50543(17) 0.0348(5) Uani 1 1 d . . . H20 H 0.5011 0.5760 0.4421 0.042 Uiso 1 1 calc R . . C21 C 0.57642(19) 0.74610(19) 0.54919(17) 0.0341(5) Uani 1 1 d . . . H21 H 0.6395 0.7524 0.5155 0.041 Uiso 1 1 calc R . . C22 C 0.56755(18) 0.84244(18) 0.64185(17) 0.0309(5) Uani 1 1 d . . . H22 H 0.6236 0.9145 0.6721 0.037 Uiso 1 1 calc R . . C23 C 0.47405(18) 0.82940(17) 0.68839(16) 0.0285(4) Uani 1 1 d . . . C24 C 0.43452(17) 0.90831(17) 0.78369(16) 0.0261(4) Uani 1 1 d . . . C25 C 0.38618(17) 1.09354(17) 0.99194(16) 0.0264(4) Uani 1 1 d . . . H25 H 0.3356 1.0190 0.9657 0.032 Uiso 1 1 calc R . . C26 C 0.47170(17) 1.10947(16) 0.93751(16) 0.0263(4) Uani 1 1 d . . . C27 C 0.54544(17) 1.21903(17) 0.97501(16) 0.0278(4) Uani 1 1 d . . . C28 C 0.53526(17) 1.31233(17) 1.06902(16) 0.0278(4) Uani 1 1 d . . . H28 H 0.5867 1.3865 1.0957 0.033 Uiso 1 1 calc R . . C29 C 0.45056(17) 1.29764(16) 1.12389(16) 0.0267(4) Uani 1 1 d . . . C30 C 0.37544(17) 1.18792(17) 1.08533(16) 0.0260(4) Uani 1 1 d . . . C31 C 0.1273(2) 0.9007(3) 0.3718(2) 0.0579(7) Uani 1 1 d . . . H31 H 0.0524 0.9163 0.3507 0.069 Uiso 1 1 calc R . . C32 C 0.1922(2) 0.8648(2) 0.2934(2) 0.0496(6) Uani 1 1 d . . . H32 H 0.1623 0.8553 0.2201 0.060 Uiso 1 1 calc R . . C33 C 0.2999(2) 0.8433(2) 0.3237(2) 0.0543(7) Uani 1 1 d . . . H33 H 0.3460 0.8172 0.2713 0.065 Uiso 1 1 calc R . . C34 C 0.3415(3) 0.8598(3) 0.4310(2) 0.0597(7) Uani 1 1 d . . . H34 H 0.4176 0.8478 0.4549 0.072 Uiso 1 1 calc R . . C35 C 0.2697(3) 0.8941(2) 0.5030(2) 0.0556(7) Uani 1 1 d . . . H35 H 0.2977 0.9036 0.5766 0.067 Uiso 1 1 calc R . . C36 C 0.5577(2) 0.68035(19) 0.26067(18) 0.0388(5) Uani 1 1 d . . . H36 H 0.4763 0.6716 0.2289 0.047 Uiso 1 1 calc R . . C37 C 0.6335(2) 0.7867(2) 0.2965(2) 0.0436(6) Uani 1 1 d . . . H37 H 0.6048 0.8493 0.2887 0.052 Uiso 1 1 calc R . . C38 C 0.7518(2) 0.8008(2) 0.3441(2) 0.0431(6) Uani 1 1 d . . . H38 H 0.8058 0.8737 0.3713 0.052 Uiso 1 1 calc R . . C39 C 0.7895(2) 0.7064(2) 0.35109(19) 0.0407(5) Uani 1 1 d . . . H39 H 0.8707 0.7129 0.3818 0.049 Uiso 1 1 calc R . . C40 C 0.7086(2) 0.60295(19) 0.31316(18) 0.0369(5) Uani 1 1 d . . . H40 H 0.7356 0.5387 0.3189 0.044 Uiso 1 1 calc R . . C41 C 0.69190(19) 0.54331(19) 0.00515(18) 0.0339(5) Uani 1 1 d . . . H41 H 0.6104 0.5313 -0.0286 0.041 Uiso 1 1 calc R . . C42 C 0.75792(19) 0.65585(19) 0.06414(18) 0.0357(5) Uani 1 1 d . . . H42 H 0.7229 0.7201 0.0704 0.043 Uiso 1 1 calc R . . C43 C 0.8766(2) 0.67359(19) 0.11419(19) 0.0391(5) Uani 1 1 d . . . H43 H 0.9247 0.7503 0.1550 0.047 Uiso 1 1 calc R . . C44 C 0.9238(2) 0.5783(2) 0.10388(19) 0.0403(5) Uani 1 1 d . . . H44 H 1.0046 0.5879 0.1385 0.048 Uiso 1 1 calc R . . C45 C 0.8513(2) 0.4690(2) 0.0422(2) 0.0393(5) Uani 1 1 d . . . H45 H 0.8846 0.4034 0.0343 0.047 Uiso 1 1 calc R . . H1N H 0.2985(19) 1.243(2) 1.204(2) 0.037(6) Uiso 1 1 d . . . H4N H 0.192(2) 0.826(2) 0.889(2) 0.041(7) Uiso 1 1 d . . . H7N H 0.561(2) 1.043(2) 0.828(2) 0.042(7) Uiso 1 1 d . . . N1 N 0.29205(14) 1.18139(15) 1.14665(14) 0.0268(4) Uani 1 1 d . . . N2 N 0.17814(14) 0.98717(14) 1.04467(13) 0.0265(4) Uani 1 1 d . . . N3 N 0.01189(14) 0.82334(14) 0.98707(13) 0.0275(4) Uani 1 1 d . . . N4 N 0.13935(16) 0.76722(16) 0.85709(14) 0.0287(4) Uani 1 1 d . . . N5 N 0.21737(14) 0.66024(14) 0.69619(14) 0.0297(4) Uani 1 1 d . . . N6 N 0.33818(14) 0.85743(14) 0.79869(13) 0.0278(4) Uani 1 1 d . . . N7 N 0.49221(15) 1.02041(14) 0.84385(13) 0.0276(4) Uani 1 1 d . . . N8 N 0.1642(2) 0.91451(19) 0.47534(19) 0.0557(6) Uani 1 1 d . . . N9 N 0.59303(16) 0.58872(15) 0.26839(14) 0.0360(4) Uani 1 1 d . . . N10 N 0.73729(16) 0.44972(15) -0.00694(15) 0.0344(4) Uani 1 1 d . . . O1 O 0.43465(12) 1.38685(12) 1.21534(11) 0.0325(3) Uani 1 1 d . . . H1 H 0.4832 1.4485 1.2309 0.049 Uiso 1 1 calc R . . O2 O 0.62519(12) 1.22817(12) 0.91538(12) 0.0345(4) Uani 1 1 d . . . H2 H 0.6649 1.2971 0.9445 0.052 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 C1 0.0267(10) 0.0268(10) 0.0235(9) 0.0113(8) 0.0061(8) 0.0075(8) C2 0.0298(10) 0.0300(10) 0.0234(10) 0.0126(8) 0.0087(8) 0.0104(8) C3 0.0365(11) 0.0306(11) 0.0264(10) 0.0106(9) 0.0096(9) 0.0104(9) C4 0.0421(12) 0.0352(12) 0.0263(11) 0.0119(9) 0.0125(9) 0.0156(10) C5 0.0381(12) 0.0377(12) 0.0312(11) 0.0179(9) 0.0173(9) 0.0149(10) C6 0.0348(11) 0.0326(11) 0.0307(11) 0.0165(9) 0.0135(9) 0.0106(9) C7 0.0318(11) 0.0288(10) 0.0247(10) 0.0134(8) 0.0096(8) 0.0124(9) C8 0.0292(10) 0.0295(10) 0.0238(10) 0.0132(8) 0.0074(8) 0.0098(8) C9 0.0295(10) 0.0281(10) 0.0287(10) 0.0147(8) 0.0101(8) 0.0096(8) C10 0.0352(11) 0.0247(10) 0.0285(10) 0.0098(8) 0.0072(9) 0.0105(9) C11 0.0338(12) 0.0403(13) 0.0426(13) 0.0205(11) 0.0075(10) 0.0062(10) C12 0.0382(13) 0.0378(13) 0.0473(14) 0.0159(11) 0.0093(11) 0.0027(10) C13 0.0420(13) 0.0339(12) 0.0399(13) 0.0062(10) 0.0061(11) 0.0041(10) C14 0.0378(12) 0.0356(12) 0.0364(12) 0.0107(10) 0.0061(10) 0.0102(10) C15 0.0330(11) 0.0327(11) 0.0375(12) 0.0172(10) 0.0049(9) 0.0089(9) C16 0.0299(10) 0.0263(10) 0.0292(11) 0.0106(8) 0.0079(9) 0.0070(8) C17 0.0295(10) 0.0260(10) 0.0238(10) 0.0067(8) 0.0051(8) 0.0088(8) C18 0.0282(10) 0.0270(10) 0.0250(10) 0.0094(8) 0.0063(8) 0.0101(8) C19 0.0375(12) 0.0290(11) 0.0271(11) 0.0086(9) 0.0083(9) 0.0100(9) C20 0.0442(13) 0.0341(11) 0.0256(11) 0.0091(9) 0.0127(9) 0.0157(10) C21 0.0367(12) 0.0412(12) 0.0279(11) 0.0146(9) 0.0144(9) 0.0142(10) C22 0.0321(11) 0.0333(11) 0.0287(11) 0.0135(9) 0.0093(9) 0.0107(9) C23 0.0320(11) 0.0293(10) 0.0240(10) 0.0106(8) 0.0065(8) 0.0115(9) C24 0.0275(10) 0.0286(10) 0.0237(10) 0.0112(8) 0.0079(8) 0.0103(8) C25 0.0287(10) 0.0233(10) 0.0251(10) 0.0089(8) 0.0062(8) 0.0063(8) C26 0.0292(10) 0.0240(10) 0.0235(10) 0.0077(8) 0.0071(8) 0.0080(8) C27 0.0299(10) 0.0290(10) 0.0263(10) 0.0120(8) 0.0105(8) 0.0081(8) C28 0.0305(10) 0.0231(10) 0.0261(10) 0.0082(8) 0.0062(8) 0.0040(8) C29 0.0313(10) 0.0252(10) 0.0219(9) 0.0081(8) 0.0059(8) 0.0096(8) C30 0.0264(10) 0.0279(10) 0.0238(10) 0.0106(8) 0.0073(8) 0.0078(8) C31 0.0544(16) 0.0663(19) 0.0575(17) 0.0279(15) 0.0121(14) 0.0292(14) C32 0.0628(17) 0.0520(15) 0.0360(13) 0.0228(12) 0.0068(12) 0.0151(13) C33 0.0689(18) 0.0594(17) 0.0488(15) 0.0269(13) 0.0308(14) 0.0297(14) C34 0.0563(17) 0.0652(18) 0.0599(18) 0.0285(15) 0.0098(14) 0.0247(14) C35 0.0756(19) 0.0547(16) 0.0351(14) 0.0189(12) 0.0063(13) 0.0241(14) C36 0.0406(13) 0.0365(12) 0.0347(12) 0.0094(10) 0.0118(10) 0.0119(10) C37 0.0572(15) 0.0336(12) 0.0476(14) 0.0194(11) 0.0225(12) 0.0168(11) C38 0.0490(14) 0.0326(12) 0.0430(13) 0.0106(10) 0.0186(11) 0.0039(10) C39 0.0390(13) 0.0451(13) 0.0344(12) 0.0134(10) 0.0113(10) 0.0090(11) C40 0.0476(13) 0.0349(12) 0.0316(11) 0.0137(9) 0.0167(10) 0.0151(10) C41 0.0324(11) 0.0373(12) 0.0347(12) 0.0175(10) 0.0111(9) 0.0080(9) C42 0.0439(13) 0.0316(11) 0.0346(12) 0.0162(9) 0.0106(10) 0.0117(10) C43 0.0458(13) 0.0324(12) 0.0351(12) 0.0131(10) 0.0075(10) 0.0045(10) C44 0.0365(12) 0.0420(13) 0.0397(13) 0.0171(11) 0.0052(10) 0.0096(10) C45 0.0401(12) 0.0354(12) 0.0459(13) 0.0192(10) 0.0122(11) 0.0138(10) N1 0.0291(9) 0.0249(9) 0.0212(9) 0.0051(7) 0.0072(7) 0.0051(7) N2 0.0301(9) 0.0250(8) 0.0242(8) 0.0100(7) 0.0073(7) 0.0078(7) N3 0.0309(9) 0.0266(9) 0.0263(9) 0.0108(7) 0.0101(7) 0.0093(7) N4 0.0301(9) 0.0263(9) 0.0280(9) 0.0100(7) 0.0082(8) 0.0063(8) N5 0.0293(9) 0.0266(9) 0.0290(9) 0.0088(7) 0.0056(7) 0.0063(7) N6 0.0292(9) 0.0239(8) 0.0265(9) 0.0075(7) 0.0062(7) 0.0068(7) N7 0.0300(9) 0.0256(9) 0.0258(9) 0.0081(7) 0.0114(7) 0.0064(7) N8 0.0677(15) 0.0553(14) 0.0502(14) 0.0230(11) 0.0234(12) 0.0231(12) N9 0.0428(11) 0.0308(10) 0.0292(9) 0.0061(8) 0.0135(8) 0.0091(8) N10 0.0373(10) 0.0316(9) 0.0376(10) 0.0164(8) 0.0146(8) 0.0080(8) O1 0.0380(8) 0.0249(7) 0.0273(7) 0.0037(6) 0.0115(6) 0.0047(6) O2 0.0382(8) 0.0288(8) 0.0343(8) 0.0099(6) 0.0171(7) 0.0035(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 C1 N2 1.326(2) . ? C1 N1 1.343(3) . ? C1 C2 1.479(3) . ? C2 C3 1.389(3) . ? C2 C7 1.399(3) . ? C3 C4 1.391(3) . ? C4 C5 1.402(3) . ? C5 C6 1.388(3) . ? C6 C7 1.387(3) . ? C7 C8 1.470(3) . ? C8 N3 1.300(3) . ? C8 N2 1.416(2) . ? C9 N3 1.364(3) . ? C9 N4 1.376(2) . ? C9 C10 1.413(3) . ? C10 C11 1.394(3) . ? C10 C15 1.449(3) . ? C11 C12 1.388(3) . ? C12 C13 1.421(3) . ? C13 C14 1.374(3) . ? C14 C15 1.396(3) . ? C15 C16 1.413(3) . ? C16 N5 1.359(3) . ? C16 N4 1.378(3) . ? C17 N5 1.305(3) . ? C17 N6 1.404(2) . ? C17 C18 1.468(3) . ? C18 C19 1.392(3) . ? C18 C23 1.393(3) . ? C19 C20 1.386(3) . ? C20 C21 1.397(3) . ? C21 C22 1.395(3) . ? C22 C23 1.387(3) . ? C23 C24 1.480(3) . ? C24 N6 1.325(2) . ? C24 N7 1.343(3) . ? C25 C26 1.392(3) . ? C25 C30 1.395(3) . ? C26 C27 1.395(3) . ? C26 N7 1.409(2) . ? C27 O2 1.368(2) . ? C27 C28 1.390(3) . ? C28 C29 1.384(3) . ? C29 O1 1.370(2) . ? C29 C30 1.402(3) . ? C30 N1 1.411(2) . ? C31 N8 1.331(3) . ? C31 C32 1.383(4) . ? C32 C33 1.359(4) . ? C33 C34 1.375(4) . ? C34 C35 1.379(4) . ? C35 N8 1.322(3) . ? C36 N9 1.337(3) . ? C36 C37 1.378(3) . ? C37 C38 1.381(3) . ? C38 C39 1.380(3) . ? C39 C40 1.374(3) . ? C40 N9 1.343(3) . ? C41 N10 1.341(3) . ? C41 C42 1.375(3) . ? C42 C43 1.386(3) . ? C43 C44 1.377(3) . ? C44 C45 1.375(3) . ? C45 N10 1.330(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 N2 C1 N1 125.63(18) . . ? N2 C1 C2 113.60(17) . . ? N1 C1 C2 120.74(18) . . ? C3 C2 C7 121.42(19) . . ? C3 C2 C1 134.15(19) . . ? C7 C2 C1 104.41(17) . . ? C2 C3 C4 117.7(2) . . ? C3 C4 C5 120.94(19) . . ? C6 C5 C4 120.94(19) . . ? C7 C6 C5 118.2(2) . . ? C6 C7 C2 120.61(18) . . ? C6 C7 C8 133.07(19) . . ? C2 C7 C8 106.31(17) . . ? N3 C8 N2 127.67(18) . . ? N3 C8 C7 122.26(18) . . ? N2 C8 C7 110.06(17) . . ? N3 C9 N4 128.03(18) . . ? N3 C9 C10 124.60(18) . . ? N4 C9 C10 107.35(18) . . ? C11 C10 C9 132.5(2) . . ? C11 C10 C15 120.9(2) . . ? C9 C10 C15 106.48(18) . . ? C12 C11 C10 117.4(2) . . ? C11 C12 C13 121.7(2) . . ? C14 C13 C12 121.5(2) . . ? C13 C14 C15 118.3(2) . . ? C14 C15 C16 131.8(2) . . ? C14 C15 C10 120.2(2) . . ? C16 C15 C10 107.82(19) . . ? N5 C16 N4 129.16(18) . . ? N5 C16 C15 124.39(19) . . ? N4 C16 C15 106.45(18) . . ? N5 C17 N6 127.47(18) . . ? N5 C17 C18 122.33(18) . . ? N6 C17 C18 110.19(17) . . ? C19 C18 C23 120.97(19) . . ? C19 C18 C17 132.76(19) . . ? C23 C18 C17 106.26(17) . . ? C20 C19 C18 117.7(2) . . ? C19 C20 C21 121.44(19) . . ? C22 C21 C20 120.71(19) . . ? C23 C22 C21 117.7(2) . . ? C22 C23 C18 121.45(18) . . ? C22 C23 C24 133.97(19) . . ? C18 C23 C24 104.58(17) . . ? N6 C24 N7 125.90(18) . . ? N6 C24 C23 113.18(17) . . ? N7 C24 C23 120.90(18) . . ? C26 C25 C30 119.44(18) . . ? C25 C26 C27 120.49(18) . . ? C25 C26 N7 124.51(18) . . ? C27 C26 N7 115.00(17) . . ? O2 C27 C28 123.33(18) . . ? O2 C27 C26 116.94(17) . . ? C28 C27 C26 119.73(18) . . ? C29 C28 C27 120.32(18) . . ? O1 C29 C28 122.92(18) . . ? O1 C29 C30 117.15(17) . . ? C28 C29 C30 119.93(17) . . ? C25 C30 C29 120.07(18) . . ? C25 C30 N1 124.07(18) . . ? C29 C30 N1 115.85(17) . . ? N8 C31 C32 123.5(2) . . ? C33 C32 C31 118.3(2) . . ? C32 C33 C34 119.3(2) . . ? C33 C34 C35 118.2(3) . . ? N8 C35 C34 123.7(2) . . ? N9 C36 C37 123.3(2) . . ? C36 C37 C38 118.9(2) . . ? C39 C38 C37 118.3(2) . . ? C40 C39 C38 119.4(2) . . ? N9 C40 C39 122.8(2) . . ? N10 C41 C42 123.0(2) . . ? C41 C42 C43 118.6(2) . . ? C44 C43 C42 118.9(2) . . ? C45 C44 C43 118.4(2) . . ? N10 C45 C44 123.8(2) . . ? C1 N1 C30 130.77(17) . . ? C1 N2 C8 105.45(16) . . ? C8 N3 C9 124.48(18) . . ? C9 N4 C16 111.89(18) . . ? C17 N5 C16 123.95(18) . . ? C24 N6 C17 105.79(16) . . ? C24 N7 C26 130.53(18) . . ? C35 N8 C31 116.9(2) . . ? C36 N9 C40 117.28(19) . . ? C45 N10 C41 117.26(19) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.25 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.871 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.070 data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H25.4 N6 O2.7' _chemical_formula_weight 441.16 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 7.6457(16) _cell_length_b 9.891(2) _cell_length_c 15.431(3) _cell_angle_alpha 97.881(3) _cell_angle_beta 101.751(3) _cell_angle_gamma 93.578(3) _cell_volume 1126.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3687 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.86 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 466 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9699 _exptl_absorpt_correction_T_max 0.9741 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.043210 ; _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 '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 9095 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 26.75 _reflns_number_total 4686 _reflns_number_gt 3688 _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. Hydrogen atoms were assigned ideal positions and refined isotropically as riding atoms, with the exception of one of the methanol hydroxide hydrogen atoms. Disordered solvent molecules, other than the well ordered methanol solvents, equivalent to 14 electrons per unit cell were modeled by using the SQUEEZE program. The formula, density, F(000) and other parameters reflect the presence of this modeled solvent without atom positions. ; _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^)+(0.0902P)^2^+0.1014P] 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 4686 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1511 _refine_ls_wR_factor_gt 0.1443 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 C1 C 0.1810(2) 0.22398(17) 0.05670(11) 0.0231(4) Uani 1 1 d . . . C2 C 0.1945(2) 0.09841(17) -0.00448(11) 0.0236(4) Uani 1 1 d . . . C3 C 0.1356(2) 0.05962(19) -0.09605(12) 0.0292(4) Uani 1 1 d . . . H3 H 0.0738 0.1191 -0.1325 0.035 Uiso 1 1 calc R . . C4 C 0.1703(3) -0.0699(2) -0.13260(12) 0.0335(4) Uani 1 1 d . . . H4 H 0.1317 -0.0995 -0.1952 0.040 Uiso 1 1 calc R . . C5 C 0.2601(3) -0.15657(19) -0.07943(12) 0.0325(4) Uani 1 1 d . . . H5 H 0.2816 -0.2445 -0.1063 0.039 Uiso 1 1 calc R . . C6 C 0.3197(2) -0.11758(18) 0.01268(12) 0.0275(4) Uani 1 1 d . . . H6 H 0.3817 -0.1770 0.0491 0.033 Uiso 1 1 calc R . . C7 C 0.2849(2) 0.01114(17) 0.04902(11) 0.0227(4) Uani 1 1 d . . . C8 C 0.3271(2) 0.08439(16) 0.14243(11) 0.0208(3) Uani 1 1 d . . . C9 C 0.5510(2) 0.24286(16) 0.31170(10) 0.0193(3) Uani 1 1 d . . . H9 H 0.5897 0.2768 0.2634 0.023 Uiso 1 1 calc R . . C10 C 0.4480(2) 0.11740(16) 0.29658(10) 0.0192(3) Uani 1 1 d . . . C11 C 0.3944(2) 0.06617(16) 0.36763(11) 0.0216(3) Uani 1 1 d . . . H11 H 0.3273 -0.0207 0.3579 0.026 Uiso 1 1 calc R . . C12 C 0.4393(2) 0.14262(17) 0.45278(11) 0.0233(4) Uani 1 1 d . . . H12 H 0.3997 0.1087 0.5009 0.028 Uiso 1 1 calc R . . C13 C 0.5413(2) 0.26788(16) 0.46849(11) 0.0209(3) Uani 1 1 d . . . H13 H 0.5728 0.3187 0.5272 0.025 Uiso 1 1 calc R . . C14 C 0.5977(2) 0.31923(16) 0.39774(10) 0.0187(3) Uani 1 1 d . . . C15 C 0.6695(2) 0.54342(16) 0.37529(10) 0.0190(3) Uani 1 1 d . . . C16 C 0.7873(2) 0.67175(15) 0.38713(10) 0.0185(3) Uani 1 1 d . . . C17 C 0.9581(2) 0.71172(16) 0.43822(11) 0.0218(4) Uani 1 1 d . . . H17 H 1.0206 0.6533 0.4752 0.026 Uiso 1 1 calc R . . C18 C 1.0343(2) 0.84058(17) 0.43319(11) 0.0251(4) Uani 1 1 d . . . H18 H 1.1507 0.8715 0.4682 0.030 Uiso 1 1 calc R . . C19 C 0.9438(2) 0.92604(17) 0.37780(12) 0.0259(4) Uani 1 1 d . . . H19 H 1.0004 1.0132 0.3752 0.031 Uiso 1 1 calc R . . C20 C 0.7723(2) 0.88551(16) 0.32654(11) 0.0221(4) Uani 1 1 d . . . H20 H 0.7101 0.9433 0.2889 0.026 Uiso 1 1 calc R . . C21 C 0.6956(2) 0.75764(16) 0.33253(10) 0.0192(3) Uani 1 1 d . . . C22 C 0.5194(2) 0.68297(16) 0.28742(10) 0.0200(3) Uani 1 1 d . . . C23 C 0.1086(2) 0.36130(19) 0.34161(12) 0.0316(4) Uani 1 1 d . . . H23A H 0.1496 0.2735 0.3561 0.047 Uiso 1 1 calc R . . H23B H -0.0223 0.3515 0.3215 0.047 Uiso 1 1 calc R . . H23C H 0.1436 0.4313 0.3950 0.047 Uiso 1 1 calc R . . C24 C 0.9316(3) 0.6016(2) 0.18610(14) 0.0365(5) Uani 1 1 d . . . H24A H 0.8980 0.5064 0.1917 0.055 Uiso 1 1 calc R . . H24B H 0.8251 0.6425 0.1580 0.055 Uiso 1 1 calc R . . H24C H 0.9818 0.6537 0.2457 0.055 Uiso 1 1 calc R . . N1 N 0.10266(19) 0.33080(15) 0.03381(10) 0.0281(3) Uani 1 1 d . . . H1A H 0.0997 0.4014 0.0748 0.034 Uiso 1 1 calc R . . H1B H 0.0526 0.3324 -0.0226 0.034 Uiso 1 1 calc R . . N2 N 0.26139(18) 0.21226(14) 0.14177(9) 0.0225(3) Uani 1 1 d . . . N3 N 0.40687(18) 0.03374(13) 0.21053(9) 0.0212(3) Uani 1 1 d . . . N4 N 0.71161(17) 0.44220(13) 0.41660(9) 0.0196(3) Uani 1 1 d . . . N5 N 0.51171(17) 0.55726(13) 0.31417(9) 0.0205(3) Uani 1 1 d . . . H5A H 0.4206 0.4940 0.2956 0.025 Uiso 1 1 calc PR . . N6 N 0.39210(19) 0.72592(14) 0.23251(9) 0.0256(3) Uani 1 1 d . . . H6A H 0.4053 0.8083 0.2179 0.031 Uiso 1 1 calc R . . O1 O 0.18851(15) 0.40131(12) 0.27214(8) 0.0250(3) Uani 1 1 d . . . H1 H 0.230(3) 0.323(2) 0.2366(14) 0.037 Uiso 1 1 d . . . O2 O 1.06170(15) 0.60460(13) 0.13234(8) 0.0283(3) Uani 1 1 d . . . H2 H 1.1542 0.6537 0.1614 0.042 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 C1 0.0217(8) 0.0264(9) 0.0217(8) 0.0056(7) 0.0050(7) 0.0005(6) C2 0.0234(8) 0.0258(9) 0.0219(9) 0.0038(7) 0.0071(7) -0.0022(7) C3 0.0316(9) 0.0329(10) 0.0213(9) 0.0052(7) 0.0036(7) -0.0055(7) C4 0.0409(11) 0.0373(11) 0.0195(9) -0.0010(8) 0.0082(8) -0.0108(8) C5 0.0423(11) 0.0258(9) 0.0292(10) -0.0031(7) 0.0150(8) -0.0060(8) C6 0.0308(9) 0.0246(9) 0.0275(9) 0.0018(7) 0.0097(7) -0.0013(7) C7 0.0212(8) 0.0262(9) 0.0205(9) 0.0034(7) 0.0058(7) -0.0021(6) C8 0.0198(8) 0.0216(8) 0.0211(8) 0.0029(6) 0.0058(6) -0.0005(6) C9 0.0208(8) 0.0208(8) 0.0181(8) 0.0071(6) 0.0043(6) 0.0054(6) C10 0.0184(8) 0.0195(8) 0.0201(8) 0.0036(6) 0.0032(6) 0.0064(6) C11 0.0232(8) 0.0163(8) 0.0267(9) 0.0056(6) 0.0066(7) 0.0035(6) C12 0.0268(9) 0.0245(9) 0.0233(9) 0.0104(7) 0.0102(7) 0.0069(7) C13 0.0245(8) 0.0226(8) 0.0167(8) 0.0036(6) 0.0051(6) 0.0067(6) C14 0.0175(7) 0.0177(8) 0.0220(8) 0.0054(6) 0.0035(6) 0.0067(6) C15 0.0186(8) 0.0210(8) 0.0170(8) 0.0010(6) 0.0042(6) 0.0027(6) C16 0.0220(8) 0.0185(8) 0.0163(8) 0.0019(6) 0.0071(6) 0.0033(6) C17 0.0213(8) 0.0222(8) 0.0217(8) 0.0030(6) 0.0037(6) 0.0048(6) C18 0.0198(8) 0.0256(9) 0.0280(9) 0.0023(7) 0.0026(7) 0.0005(7) C19 0.0249(9) 0.0205(8) 0.0332(10) 0.0049(7) 0.0085(7) 0.0003(7) C20 0.0235(8) 0.0204(8) 0.0240(9) 0.0050(6) 0.0072(7) 0.0045(6) C21 0.0207(8) 0.0203(8) 0.0178(8) 0.0019(6) 0.0069(6) 0.0047(6) C22 0.0240(8) 0.0188(8) 0.0180(8) 0.0012(6) 0.0071(6) 0.0026(6) C23 0.0343(10) 0.0335(10) 0.0304(10) 0.0062(8) 0.0126(8) 0.0080(8) C24 0.0359(10) 0.0434(12) 0.0373(11) 0.0142(9) 0.0158(9) 0.0145(9) N1 0.0309(8) 0.0304(8) 0.0228(8) 0.0073(6) 0.0019(6) 0.0075(6) N2 0.0217(7) 0.0260(7) 0.0206(7) 0.0062(6) 0.0032(6) 0.0057(6) N3 0.0230(7) 0.0198(7) 0.0203(7) 0.0029(5) 0.0044(5) 0.0002(5) N4 0.0213(7) 0.0191(7) 0.0184(7) 0.0035(5) 0.0037(5) 0.0032(5) N5 0.0216(7) 0.0177(7) 0.0211(7) 0.0043(5) 0.0014(5) 0.0019(5) N6 0.0267(7) 0.0202(7) 0.0276(8) 0.0057(6) -0.0009(6) 0.0016(6) O1 0.0251(6) 0.0238(6) 0.0264(7) 0.0030(5) 0.0065(5) 0.0036(5) O2 0.0242(6) 0.0352(7) 0.0234(6) 0.0033(5) 0.0016(5) 0.0013(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 1.302(2) . ? C1 N2 1.355(2) . ? C1 C2 1.476(2) . ? C2 C3 1.385(2) . ? C2 C7 1.393(2) . ? C3 C4 1.391(3) . ? C4 C5 1.384(3) . ? C5 C6 1.393(2) . ? C6 C7 1.383(2) . ? C7 C8 1.484(2) . ? C8 N3 1.284(2) . ? C8 N2 1.390(2) . ? C9 C10 1.392(2) . ? C9 C14 1.400(2) . ? C10 C11 1.392(2) . ? C10 N3 1.429(2) . ? C11 C12 1.388(2) . ? C12 C13 1.386(2) . ? C13 C14 1.397(2) . ? C14 N4 1.411(2) . ? C15 N4 1.282(2) . ? C15 N5 1.3988(19) . ? C15 C16 1.477(2) . ? C16 C17 1.383(2) . ? C16 C21 1.397(2) . ? C17 C18 1.387(2) . ? C18 C19 1.398(2) . ? C19 C20 1.390(2) . ? C20 C21 1.383(2) . ? C21 C22 1.483(2) . ? C22 N6 1.288(2) . ? C22 N5 1.364(2) . ? C23 O1 1.425(2) . ? C24 O2 1.421(2) . ? 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 N2 124.16(16) . . ? N1 C1 C2 125.83(16) . . ? N2 C1 C2 110.00(14) . . ? C3 C2 C7 121.34(16) . . ? C3 C2 C1 132.63(16) . . ? C7 C2 C1 106.02(14) . . ? C2 C3 C4 117.38(17) . . ? C5 C4 C3 121.25(17) . . ? C4 C5 C6 121.42(17) . . ? C7 C6 C5 117.32(17) . . ? C6 C7 C2 121.29(16) . . ? C6 C7 C8 131.68(16) . . ? C2 C7 C8 107.03(14) . . ? N3 C8 N2 127.58(15) . . ? N3 C8 C7 124.46(15) . . ? N2 C8 C7 107.94(13) . . ? C10 C9 C14 120.33(14) . . ? C11 C10 C9 119.90(15) . . ? C11 C10 N3 118.43(14) . . ? C9 C10 N3 121.49(14) . . ? C12 C11 C10 119.70(15) . . ? C13 C12 C11 120.82(15) . . ? C12 C13 C14 119.83(15) . . ? C13 C14 C9 119.40(15) . . ? C13 C14 N4 118.66(14) . . ? C9 C14 N4 121.78(14) . . ? N4 C15 N5 128.96(15) . . ? N4 C15 C16 123.62(14) . . ? N5 C15 C16 107.41(13) . . ? C17 C16 C21 121.31(15) . . ? C17 C16 C15 131.56(14) . . ? C21 C16 C15 107.12(14) . . ? C16 C17 C18 117.27(15) . . ? C17 C18 C19 121.53(15) . . ? C20 C19 C18 121.03(15) . . ? C21 C20 C19 117.32(15) . . ? C20 C21 C16 121.53(15) . . ? C20 C21 C22 131.42(14) . . ? C16 C21 C22 107.04(14) . . ? N6 C22 N5 124.35(15) . . ? N6 C22 C21 127.48(15) . . ? N5 C22 C21 108.17(13) . . ? C1 N2 C8 109.00(14) . . ? C8 N3 C10 119.04(14) . . ? C15 N4 C14 120.59(13) . . ? C22 N5 C15 110.24(14) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 26.75 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.322 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.078 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.500 0.000 76 14 ' ' _platon_squeeze_details ; ; data_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H26 N8 O2' _chemical_formula_weight 554.61 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 15.039(7) _cell_length_b 12.809(6) _cell_length_c 14.218(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2739(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3694 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 22.68 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9739 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.819477 ; _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 '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 22126 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0579 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.27 _reflns_number_total 6362 _reflns_number_gt 5080 _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. Hydrogen atoms were assigned ideal positions and refined isotropically as riding atoms. ; _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^)+(0.0470P)^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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(13) _refine_ls_number_reflns 6362 _refine_ls_number_parameters 395 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 C1 C 0.17424(15) 0.35828(16) 0.97006(15) 0.0250(5) Uani 1 1 d . . . C2 C 0.26952(14) 0.34946(17) 0.99335(15) 0.0252(5) Uani 1 1 d . . . C3 C 0.31519(16) 0.3453(2) 1.07783(17) 0.0327(6) Uani 1 1 d . . . H3 H 0.2845 0.3451 1.1362 0.039 Uiso 1 1 calc R . . C4 C 0.40740(16) 0.3416(2) 1.07414(18) 0.0363(6) Uani 1 1 d . . . H4 H 0.4406 0.3398 1.1310 0.044 Uiso 1 1 calc R . . C5 C 0.45199(15) 0.34045(19) 0.98797(18) 0.0328(5) Uani 1 1 d . . . H5 H 0.5151 0.3367 0.9871 0.039 Uiso 1 1 calc R . . C6 C 0.40565(15) 0.34474(17) 0.90363(16) 0.0286(5) Uani 1 1 d . . . H6 H 0.4359 0.3435 0.8450 0.034 Uiso 1 1 calc R . . C7 C 0.31401(15) 0.35091(17) 0.90775(16) 0.0252(5) Uani 1 1 d . . . C8 C 0.24630(14) 0.36758(16) 0.83363(15) 0.0228(5) Uani 1 1 d . . . C10 C 0.20692(14) 0.42313(16) 0.67703(15) 0.0233(5) Uani 1 1 d . . . C11 C 0.11241(14) 0.42403(17) 0.67503(15) 0.0249(5) Uani 1 1 d . . . C12 C 0.06982(13) 0.47182(19) 0.60080(16) 0.0266(5) Uani 1 1 d . . . H12 H 0.0067 0.4749 0.6023 0.032 Uiso 1 1 calc R . . C13 C 0.11311(15) 0.51607(17) 0.52357(15) 0.0241(5) Uani 1 1 d . . . C14 C 0.20790(14) 0.50897(17) 0.51979(15) 0.0226(5) Uani 1 1 d . . . C15 C 0.24922(13) 0.46373(17) 0.59782(16) 0.0234(4) Uani 1 1 d . . . H15 H 0.3123 0.4603 0.5968 0.028 Uiso 1 1 calc R . . C16 C 0.24957(14) 0.57484(16) 0.36566(15) 0.0232(5) Uani 1 1 d . . . C17 C 0.31805(15) 0.59317(16) 0.29258(15) 0.0240(5) Uani 1 1 d . . . C18 C 0.40792(15) 0.57160(18) 0.28908(16) 0.0281(5) Uani 1 1 d . . . H18 H 0.4377 0.5404 0.3409 0.034 Uiso 1 1 calc R . . C19 C 0.45360(16) 0.59730(19) 0.20668(16) 0.0306(5) Uani 1 1 d . . . H19 H 0.5156 0.5838 0.2026 0.037 Uiso 1 1 calc R . . C20 C 0.41011(16) 0.64211(19) 0.13087(16) 0.0302(5) Uani 1 1 d . . . H20 H 0.4431 0.6598 0.0761 0.036 Uiso 1 1 calc R . . C21 C 0.31982(16) 0.66164(18) 0.13324(16) 0.0282(5) Uani 1 1 d . . . H21 H 0.2899 0.6919 0.0811 0.034 Uiso 1 1 calc R . . C22 C 0.27450(15) 0.63532(17) 0.21498(15) 0.0250(5) Uani 1 1 d . . . C23 C 0.17930(15) 0.64078(16) 0.24139(16) 0.0241(5) Uani 1 1 d . . . C24 C 0.11096(19) 0.6332(2) 0.94619(19) 0.0409(6) Uani 1 1 d . . . H24 H 0.1033 0.5750 0.9867 0.049 Uiso 1 1 calc R . . C25 C 0.1058(2) 0.6160(2) 0.85065(19) 0.0471(7) Uani 1 1 d . . . H25 H 0.0941 0.5482 0.8266 0.057 Uiso 1 1 calc R . . C26 C 0.11790(18) 0.6989(2) 0.79127(19) 0.0403(6) Uani 1 1 d . . . H26 H 0.1160 0.6897 0.7250 0.048 Uiso 1 1 calc R . . C27 C 0.13285(18) 0.7952(2) 0.82933(17) 0.0394(6) Uani 1 1 d . . . H27 H 0.1409 0.8543 0.7899 0.047 Uiso 1 1 calc R . . C28 C 0.13607(17) 0.8054(2) 0.92608(17) 0.0377(6) Uani 1 1 d . . . H28 H 0.1460 0.8728 0.9517 0.045 Uiso 1 1 calc R . . C29 C 0.12007(16) 0.3272(2) 0.31071(18) 0.0360(6) Uani 1 1 d . . . H29 H 0.1137 0.4003 0.3199 0.043 Uiso 1 1 calc R . . C30 C 0.12049(17) 0.2635(2) 0.38890(18) 0.0387(6) Uani 1 1 d . . . H30 H 0.1152 0.2921 0.4503 0.046 Uiso 1 1 calc R . . C31 C 0.12876(17) 0.15771(19) 0.37598(18) 0.0369(6) Uani 1 1 d . . . H31 H 0.1285 0.1117 0.4284 0.044 Uiso 1 1 calc R . . C32 C 0.13740(17) 0.1192(2) 0.28631(18) 0.0343(6) Uani 1 1 d . . . H32 H 0.1435 0.0464 0.2755 0.041 Uiso 1 1 calc R . . C33 C 0.13699(16) 0.18870(19) 0.21242(17) 0.0324(6) Uani 1 1 d . . . H33 H 0.1434 0.1617 0.1506 0.039 Uiso 1 1 calc R . . H34 H 0.1307(15) 0.6991(19) 0.1265(19) 0.032(7) Uiso 1 1 d . . . H35 H 0.053(2) 0.665(2) 0.202(2) 0.054(9) Uiso 1 1 d . . . H36 H 0.1182(19) 0.350(2) 1.103(2) 0.062(9) Uiso 1 1 d . . . H37 H 0.0519(19) 0.369(2) 1.011(2) 0.052(9) Uiso 1 1 d . . . N1 N 0.10780(14) 0.36001(16) 1.03115(14) 0.0281(4) Uani 1 1 d . . . N2 N 0.16252(12) 0.36772(14) 0.87716(13) 0.0253(4) Uani 1 1 d . . . N4 N 0.26763(12) 0.53755(14) 0.44741(12) 0.0237(4) Uani 1 1 d . . . N5 N 0.16647(12) 0.60389(14) 0.32792(13) 0.0242(4) Uani 1 1 d . . . N6 N 0.11501(14) 0.67401(15) 0.18650(14) 0.0278(4) Uani 1 1 d . . . N7 N 0.12594(13) 0.72560(16) 0.98547(14) 0.0349(5) Uani 1 1 d . . . N8 N 0.12812(13) 0.29157(15) 0.22248(14) 0.0314(5) Uani 1 1 d . . . N3 N 0.26597(12) 0.38854(14) 0.74762(12) 0.0245(4) Uani 1 1 d . . . O1 O 0.05941(10) 0.38021(12) 0.74091(11) 0.0300(4) Uani 1 1 d . . . H1 H 0.0910 0.3531 0.7831 0.045 Uiso 1 1 calc R . . O2 O 0.06054(10) 0.56205(12) 0.45898(10) 0.0311(4) Uani 1 1 d . . . H2 H 0.0921 0.5864 0.4154 0.047 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 C1 0.0299(12) 0.0262(11) 0.0188(12) 0.0034(9) 0.0004(9) 0.0000(9) C2 0.0262(12) 0.0299(12) 0.0197(11) 0.0021(10) 0.0005(10) -0.0005(9) C3 0.0327(14) 0.0450(15) 0.0205(12) 0.0070(11) -0.0018(10) -0.0016(11) C4 0.0332(14) 0.0521(16) 0.0236(13) 0.0084(11) -0.0061(11) -0.0022(11) C5 0.0246(12) 0.0443(14) 0.0293(13) 0.0087(12) -0.0034(11) -0.0002(10) C6 0.0301(12) 0.0345(13) 0.0213(12) 0.0029(10) 0.0009(10) -0.0002(10) C7 0.0282(12) 0.0258(12) 0.0214(12) 0.0023(9) -0.0011(10) 0.0001(9) C8 0.0259(11) 0.0250(11) 0.0176(11) 0.0007(9) -0.0008(9) -0.0013(9) C10 0.0276(12) 0.0255(11) 0.0167(10) 0.0005(9) -0.0009(10) 0.0001(9) C11 0.0264(12) 0.0305(12) 0.0180(11) -0.0016(9) 0.0022(10) -0.0035(9) C12 0.0239(10) 0.0353(12) 0.0207(10) -0.0010(9) -0.0003(11) 0.0003(10) C13 0.0283(12) 0.0271(12) 0.0169(10) 0.0016(9) -0.0015(9) 0.0023(10) C14 0.0254(12) 0.0250(11) 0.0173(10) -0.0022(9) 0.0017(9) -0.0007(9) C15 0.0235(10) 0.0277(11) 0.0188(10) -0.0033(9) -0.0012(10) 0.0012(9) C16 0.0270(12) 0.0236(11) 0.0189(11) -0.0013(9) -0.0002(9) -0.0022(8) C17 0.0293(12) 0.0277(12) 0.0151(10) -0.0008(9) -0.0015(9) -0.0027(9) C18 0.0284(12) 0.0351(13) 0.0207(12) 0.0015(10) -0.0022(10) -0.0010(10) C19 0.0268(12) 0.0407(13) 0.0242(12) 0.0001(10) -0.0004(10) -0.0004(10) C20 0.0322(14) 0.0398(14) 0.0185(11) 0.0014(10) 0.0044(10) -0.0049(10) C21 0.0335(14) 0.0340(13) 0.0172(11) 0.0020(10) -0.0018(10) -0.0028(10) C22 0.0285(12) 0.0268(11) 0.0198(11) -0.0016(9) 0.0002(9) -0.0020(9) C23 0.0295(12) 0.0244(11) 0.0183(11) -0.0002(9) 0.0002(10) -0.0024(9) C24 0.0592(18) 0.0331(13) 0.0304(14) 0.0068(11) 0.0095(13) 0.0028(12) C25 0.076(2) 0.0322(13) 0.0333(15) -0.0021(12) 0.0040(14) 0.0049(13) C26 0.0596(18) 0.0416(16) 0.0198(12) -0.0010(11) -0.0016(12) 0.0060(12) C27 0.0560(17) 0.0381(14) 0.0240(14) 0.0061(11) 0.0000(12) -0.0048(12) C28 0.0458(16) 0.0393(14) 0.0279(14) 0.0026(12) -0.0023(12) -0.0147(11) C29 0.0473(15) 0.0314(13) 0.0293(14) -0.0013(11) 0.0032(12) -0.0011(11) C30 0.0551(17) 0.0405(15) 0.0205(13) -0.0005(11) 0.0048(11) 0.0013(12) C31 0.0490(16) 0.0377(14) 0.0240(13) 0.0055(12) 0.0002(12) 0.0019(11) C32 0.0418(15) 0.0323(13) 0.0290(13) -0.0005(11) -0.0004(11) 0.0050(11) C33 0.0370(13) 0.0386(14) 0.0216(12) -0.0044(11) 0.0002(10) 0.0028(11) N1 0.0267(11) 0.0407(12) 0.0171(10) 0.0052(9) 0.0002(8) 0.0031(9) N2 0.0264(10) 0.0319(10) 0.0176(9) 0.0020(8) 0.0008(8) -0.0007(8) N4 0.0264(10) 0.0282(10) 0.0166(9) 0.0019(7) 0.0015(8) -0.0004(8) N5 0.0259(9) 0.0284(9) 0.0182(9) 0.0008(8) -0.0014(8) 0.0006(8) N6 0.0286(11) 0.0373(11) 0.0173(10) 0.0055(9) 0.0002(9) -0.0005(9) N7 0.0388(12) 0.0421(12) 0.0239(11) 0.0052(10) 0.0018(9) -0.0037(9) N8 0.0369(12) 0.0355(11) 0.0219(11) 0.0026(9) 0.0028(9) 0.0023(9) N3 0.0270(10) 0.0287(10) 0.0179(10) 0.0004(8) 0.0000(8) -0.0001(8) O1 0.0259(8) 0.0448(10) 0.0193(8) 0.0079(7) -0.0020(7) -0.0042(7) O2 0.0270(9) 0.0457(10) 0.0205(9) 0.0098(7) 0.0004(7) 0.0046(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 C1 N1 1.324(3) . ? C1 N2 1.338(3) . ? C1 C2 1.475(3) . ? C2 C3 1.385(3) . ? C2 C7 1.389(3) . ? C3 C4 1.389(3) . ? C4 C5 1.397(3) . ? C5 C6 1.388(3) . ? C6 C7 1.382(3) . ? C7 C8 1.481(3) . ? C8 N3 1.286(3) . ? C8 N2 1.404(3) . ? C10 C15 1.394(3) . ? C10 N3 1.412(3) . ? C10 C11 1.422(3) . ? C11 O1 1.352(3) . ? C11 C12 1.378(3) . ? C12 C13 1.397(3) . ? C13 O2 1.347(3) . ? C13 C14 1.429(3) . ? C14 C15 1.397(3) . ? C14 N4 1.414(3) . ? C16 N4 1.286(3) . ? C16 N5 1.410(3) . ? C16 C17 1.482(3) . ? C17 C18 1.380(3) . ? C17 C22 1.392(3) . ? C18 C19 1.397(3) . ? C19 C20 1.385(3) . ? C20 C21 1.381(3) . ? C21 C22 1.389(3) . ? C22 C23 1.482(3) . ? C23 N6 1.314(3) . ? C23 N5 1.332(3) . ? C24 N7 1.327(3) . ? C24 C25 1.378(4) . ? C25 C26 1.369(4) . ? C26 C27 1.365(4) . ? C27 C28 1.382(3) . ? C28 N7 1.334(3) . ? C29 N8 1.341(3) . ? C29 C30 1.379(4) . ? C30 C31 1.373(3) . ? C31 C32 1.373(3) . ? C32 C33 1.377(3) . ? C33 N8 1.332(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 N1 C1 N2 123.1(2) . . ? N1 C1 C2 126.0(2) . . ? N2 C1 C2 110.88(19) . . ? C3 C2 C7 121.4(2) . . ? C3 C2 C1 132.8(2) . . ? C7 C2 C1 105.68(19) . . ? C2 C3 C4 117.6(2) . . ? C3 C4 C5 120.9(2) . . ? C6 C5 C4 121.1(2) . . ? C7 C6 C5 117.8(2) . . ? C6 C7 C2 121.1(2) . . ? C6 C7 C8 131.6(2) . . ? C2 C7 C8 107.11(19) . . ? N3 C8 N2 128.7(2) . . ? N3 C8 C7 123.3(2) . . ? N2 C8 C7 107.67(19) . . ? C15 C10 N3 113.85(19) . . ? C15 C10 C11 115.92(19) . . ? N3 C10 C11 130.2(2) . . ? O1 C11 C12 116.17(19) . . ? O1 C11 C10 124.9(2) . . ? C12 C11 C10 118.92(19) . . ? C11 C12 C13 124.45(19) . . ? O2 C13 C12 116.1(2) . . ? O2 C13 C14 126.0(2) . . ? C12 C13 C14 117.9(2) . . ? C15 C14 N4 113.74(19) . . ? C15 C14 C13 116.1(2) . . ? N4 C14 C13 130.1(2) . . ? C10 C15 C14 126.38(19) . . ? N4 C16 N5 129.0(2) . . ? N4 C16 C17 123.1(2) . . ? N5 C16 C17 107.90(18) . . ? C18 C17 C22 120.6(2) . . ? C18 C17 C16 132.4(2) . . ? C22 C17 C16 106.87(19) . . ? C17 C18 C19 117.7(2) . . ? C20 C19 C18 121.2(2) . . ? C21 C20 C19 121.4(2) . . ? C20 C21 C22 117.3(2) . . ? C21 C22 C17 121.8(2) . . ? C21 C22 C23 132.4(2) . . ? C17 C22 C23 105.78(19) . . ? N6 C23 N5 123.9(2) . . ? N6 C23 C22 125.2(2) . . ? N5 C23 C22 110.94(19) . . ? N7 C24 C25 124.5(2) . . ? C26 C25 C24 118.4(3) . . ? C27 C26 C25 118.6(2) . . ? C26 C27 C28 119.0(2) . . ? N7 C28 C27 123.6(2) . . ? N8 C29 C30 123.5(2) . . ? C31 C30 C29 118.5(2) . . ? C30 C31 C32 119.2(2) . . ? C31 C32 C33 118.4(2) . . ? N8 C33 C32 123.9(2) . . ? C1 N2 C8 108.48(19) . . ? C16 N4 C14 128.31(19) . . ? C23 N5 C16 108.46(18) . . ? C24 N7 C28 115.8(2) . . ? C33 N8 C29 116.5(2) . . ? C8 N3 C10 126.63(19) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.276 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.045