Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Alexander Kornienko' _publ_contact_author_address ; Department of Chemistry New Mexico Institute of Mining and Technology 801 Leroy Place Socorro New Mexico 87801 UNITED STATES OF AMERICA ; _publ_contact_author_email AKORNIEN@NMT.EDU _publ_section_title ; Three-component synthesis and anticancer evaluation of polycyclic indenopyridines lead to the discovery of a novel indenoheterocycle with potent apoptosis inducing properties ; _publ_section_references ; Bruker (2001). SAINTP+ for NT. Data Reduction and Correction Program v. 6.2, Bruker AXS, Madison, Wisconsin, USA. Bruker (2005). APEX2 software package. Bruker Molecular Analysis Research Tool, v. 1.27. Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2003). SADABS v.2.03, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2001). SHELXTL NT v. 6.12, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; loop_ _publ_author_name 'Alexander Kornienko' 'Lisa A. Anderson' 'Mikhail Yu. Antipin' 'Karen M. Cotter' 'Igor V. Magedov' ; M.Manpadi ; 'Amber J. Ortega' 'Shiva K. Rastogi' 'Snezna Rogelj' 'Wim F. A. Steelant' 'Paul Tongwa' ; P.Y.Uglinskii ; 'S.Van Slambrouck' 'Yin-Shan C. Wong' data_paul1 _database_code_depnum_ccdc_archive 'CCDC 660957' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H17 N3 O3' _chemical_formula_sum 'C26 H17 N3 O3' _chemical_formula_weight 419.43 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 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.3871(16) _cell_length_b 18.131(3) _cell_length_c 19.855(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4099.2(10) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9531 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 29.4 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9459 _exptl_absorpt_correction_T_max 0.9720 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II 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 69722 _diffrn_reflns_av_R_equivalents 0.0911 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 29.00 _reflns_number_total 5418 _reflns_number_gt 3443 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT+ ver. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINT+ ver. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXTL ver. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL ver. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL ver. 6.12 (Sheldrick, 2001)' _computing_publication_material 'SHELXTL ver. 6.12 (Sheldrick, 2001)' _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^)+(0.0300P)^2^+2.0000P] 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 5418 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0849 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 -0.09850(10) 0.16398(7) 0.32452(6) 0.0290(3) Uani 1 1 d . . . O2 O 0.31884(10) 0.17517(7) 0.51086(6) 0.0311(3) Uani 1 1 d . . . O3 O 0.28588(10) -0.02429(7) 0.25168(6) 0.0319(3) Uani 1 1 d . . . N1 N 0.57292(11) -0.05101(7) 0.30489(6) 0.0219(3) Uani 1 1 d . . . H1AA H 0.6407 -0.0743 0.3040 0.026 Uiso 1 1 calc R . . N2 N 0.60521(12) 0.01976(7) 0.40368(6) 0.0213(3) Uani 1 1 d . . . N3 N 0.48147(11) -0.05702(7) 0.25772(7) 0.0220(3) Uani 1 1 d . . . C1 C 0.41773(16) -0.10858(10) 0.15123(9) 0.0273(4) Uani 1 1 d . . . H1A H 0.3762(16) -0.0654(11) 0.1409(9) 0.030(5) Uiso 1 1 d . . . C2 C 0.41590(17) -0.16639(11) 0.10535(9) 0.0322(4) Uani 1 1 d . . . H2A H 0.3712(18) -0.1617(11) 0.0645(11) 0.044(6) Uiso 1 1 d . . . C3 C 0.48147(16) -0.22957(10) 0.11738(9) 0.0315(4) Uani 1 1 d . . . H3A H 0.4797(16) -0.2702(10) 0.0831(9) 0.033(5) Uiso 1 1 d . . . C4 C 0.54904(16) -0.23538(10) 0.17498(9) 0.0286(4) Uani 1 1 d . . . H4A H 0.5945(16) -0.2806(10) 0.1836(9) 0.029(5) Uiso 1 1 d . . . C5 C 0.55030(15) -0.17839(9) 0.22187(9) 0.0247(4) Uani 1 1 d . . . H5A H 0.5905(17) -0.1828(10) 0.2628(9) 0.033(5) Uiso 1 1 d . . . C6 C 0.48398(14) -0.11541(9) 0.20988(8) 0.0213(3) Uani 1 1 d . . . C9 C 0.38259(14) -0.01971(9) 0.27953(8) 0.0229(3) Uani 1 1 d . . . C11 C 0.53602(13) -0.00205(9) 0.35225(7) 0.0197(3) Uani 1 1 d . . . C12 C 0.42916(14) 0.08772(8) 0.44081(8) 0.0199(3) Uani 1 1 d . . . C13 C 0.41937(13) 0.01966(9) 0.34003(8) 0.0204(3) Uani 1 1 d . . . C15 C 0.36044(14) 0.06659(9) 0.38561(8) 0.0202(3) Uani 1 1 d . . . C16 C 0.23853(14) 0.09158(9) 0.37237(8) 0.0208(3) Uani 1 1 d . . . C17 C 0.20834(14) 0.11578(9) 0.30769(8) 0.0225(3) Uani 1 1 d . . . H17A H 0.2684(15) 0.1148(9) 0.2699(8) 0.019(4) Uiso 1 1 d . . . C18 C 0.09518(15) 0.13936(9) 0.29363(8) 0.0240(3) Uani 1 1 d . . . H18A H 0.0783(15) 0.1595(9) 0.2477(9) 0.024(4) Uiso 1 1 d . . . C19 C 0.00953(14) 0.13791(9) 0.34368(8) 0.0238(3) Uani 1 1 d . . . C21 C -0.19177(17) 0.16081(12) 0.37342(11) 0.0339(4) Uani 1 1 d . . . H21A H -0.256(2) 0.1844(13) 0.3507(11) 0.058(7) Uiso 1 1 d . . . H21B H -0.2086(17) 0.1083(12) 0.3875(9) 0.039(6) Uiso 1 1 d . . . H21C H -0.1755(18) 0.1940(12) 0.4148(11) 0.045(6) Uiso 1 1 d . . . C22 C 0.03748(15) 0.11324(9) 0.40815(8) 0.0241(3) Uani 1 1 d . . . H22A H -0.0189(16) 0.1125(10) 0.4437(9) 0.029(5) Uiso 1 1 d . . . C23 C 0.15205(15) 0.09090(9) 0.42208(8) 0.0228(3) Uani 1 1 d . . . H23A H 0.1731(14) 0.0747(9) 0.4684(8) 0.021(4) Uiso 1 1 d . . . C24 C 0.54813(13) 0.06385(8) 0.44593(8) 0.0196(3) Uani 1 1 d . . . C25 C 0.60258(14) 0.09737(8) 0.50603(8) 0.0213(3) Uani 1 1 d . . . C26 C 0.51937(14) 0.14232(9) 0.53759(8) 0.0220(3) Uani 1 1 d . . . C27 C 0.40722(15) 0.13954(9) 0.49841(8) 0.0225(3) Uani 1 1 d . . . C29 C 0.71517(15) 0.09004(9) 0.53216(8) 0.0247(4) Uani 1 1 d . . . H29A H 0.7737(16) 0.0587(9) 0.5093(8) 0.024(5) Uiso 1 1 d . . . C30 C 0.74224(17) 0.12847(10) 0.59076(9) 0.0287(4) Uani 1 1 d . . . H30A H 0.8158(17) 0.1242(10) 0.6114(9) 0.027(5) Uiso 1 1 d . . . C31 C 0.65946(17) 0.17338(10) 0.62225(9) 0.0299(4) Uani 1 1 d . . . H31A H 0.6807(16) 0.2005(10) 0.6616(9) 0.031(5) Uiso 1 1 d . . . C32 C 0.54612(16) 0.18094(9) 0.59579(8) 0.0263(4) Uani 1 1 d . . . H32A H 0.4886(16) 0.2129(10) 0.6165(9) 0.025(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 0.0167(6) 0.0390(7) 0.0314(6) 0.0032(5) 0.0001(5) 0.0054(5) O2 0.0233(6) 0.0362(7) 0.0337(7) -0.0098(6) 0.0024(5) 0.0033(5) O3 0.0189(6) 0.0408(7) 0.0361(7) -0.0131(6) -0.0096(5) 0.0041(5) N1 0.0145(6) 0.0293(7) 0.0217(7) -0.0052(6) -0.0032(5) 0.0029(6) N2 0.0190(7) 0.0246(7) 0.0203(6) -0.0011(5) -0.0005(5) -0.0022(6) N3 0.0156(6) 0.0291(7) 0.0212(7) -0.0042(6) -0.0025(5) -0.0001(6) C1 0.0251(9) 0.0314(9) 0.0254(9) -0.0029(7) -0.0018(7) 0.0023(8) C2 0.0278(10) 0.0412(11) 0.0276(9) -0.0093(8) -0.0042(8) -0.0008(8) C3 0.0313(10) 0.0307(9) 0.0325(10) -0.0120(8) 0.0059(8) -0.0058(8) C4 0.0284(9) 0.0244(9) 0.0330(9) 0.0000(7) 0.0085(8) -0.0010(7) C5 0.0223(9) 0.0300(9) 0.0216(8) 0.0019(7) 0.0030(7) -0.0007(7) C6 0.0172(8) 0.0253(8) 0.0214(8) -0.0014(6) 0.0024(6) -0.0028(6) C9 0.0176(8) 0.0269(8) 0.0242(8) -0.0007(7) -0.0001(6) 0.0005(7) C11 0.0169(8) 0.0226(8) 0.0196(7) 0.0005(6) 0.0017(6) -0.0021(6) C12 0.0182(8) 0.0215(7) 0.0201(7) 0.0010(6) 0.0018(6) -0.0004(6) C13 0.0164(8) 0.0235(8) 0.0214(8) 0.0003(6) 0.0001(6) -0.0015(6) C15 0.0184(8) 0.0216(8) 0.0206(8) 0.0018(6) 0.0011(6) -0.0017(6) C16 0.0183(8) 0.0202(8) 0.0240(8) -0.0021(6) 0.0000(6) -0.0005(6) C17 0.0199(8) 0.0256(8) 0.0220(8) -0.0021(7) 0.0015(7) 0.0003(7) C18 0.0225(8) 0.0274(8) 0.0222(8) 0.0010(7) -0.0002(7) 0.0011(7) C19 0.0172(8) 0.0261(8) 0.0282(9) -0.0014(7) -0.0021(7) 0.0020(6) C21 0.0181(9) 0.0446(12) 0.0389(11) 0.0029(9) 0.0040(8) 0.0041(8) C22 0.0187(8) 0.0293(8) 0.0243(8) 0.0004(7) 0.0046(7) 0.0006(7) C23 0.0218(9) 0.0263(8) 0.0203(8) 0.0002(7) 0.0005(6) 0.0014(7) C24 0.0192(8) 0.0208(7) 0.0187(7) 0.0020(6) 0.0013(6) -0.0024(6) C25 0.0224(8) 0.0217(8) 0.0198(8) 0.0024(6) 0.0000(6) -0.0032(6) C26 0.0230(8) 0.0215(8) 0.0216(8) 0.0019(6) -0.0001(6) -0.0048(7) C27 0.0214(8) 0.0235(8) 0.0228(8) 0.0004(6) 0.0028(7) -0.0022(7) C29 0.0245(9) 0.0251(8) 0.0244(8) 0.0002(7) -0.0021(7) -0.0027(7) C30 0.0272(10) 0.0316(9) 0.0274(9) 0.0005(8) -0.0077(8) -0.0038(8) C31 0.0347(10) 0.0314(9) 0.0235(9) -0.0066(8) -0.0042(8) -0.0066(8) C32 0.0290(9) 0.0252(8) 0.0246(8) -0.0026(7) 0.0015(7) -0.0034(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 O1 C19 1.3716(19) . ? O1 C21 1.440(2) . ? O2 C27 1.2211(19) . ? O3 C9 1.2351(19) . ? N1 C11 1.3596(19) . ? N1 N3 1.4048(18) . ? N1 H1AA 0.8800 . ? N2 C24 1.329(2) . ? N2 C11 1.3491(19) . ? N3 C9 1.383(2) . ? N3 C6 1.423(2) . ? C1 C2 1.389(2) . ? C1 C6 1.393(2) . ? C1 H1A 0.937(19) . ? C2 C3 1.388(3) . ? C2 H2A 0.96(2) . ? C3 C4 1.382(3) . ? C3 H3A 1.003(19) . ? C4 C5 1.391(2) . ? C4 H4A 0.984(19) . ? C5 C6 1.390(2) . ? C5 H5A 0.936(19) . ? C9 C13 1.459(2) . ? C11 C13 1.407(2) . ? C12 C15 1.400(2) . ? C12 C24 1.426(2) . ? C12 C27 1.501(2) . ? C13 C15 1.412(2) . ? C15 C16 1.484(2) . ? C16 C23 1.394(2) . ? C16 C17 1.400(2) . ? C17 C18 1.386(2) . ? C17 H17A 1.015(16) . ? C18 C19 1.393(2) . ? C18 H18A 1.001(17) . ? C19 C22 1.393(2) . ? C21 H21A 0.96(2) . ? C21 H21B 1.01(2) . ? C21 H21C 1.03(2) . ? C22 C23 1.394(2) . ? C22 H22A 0.954(18) . ? C23 H23A 0.995(16) . ? C24 C25 1.476(2) . ? C25 C29 1.389(2) . ? C25 C26 1.398(2) . ? C26 C32 1.385(2) . ? C26 C27 1.496(2) . ? C29 C30 1.391(2) . ? C29 H29A 0.987(18) . ? C30 C31 1.394(3) . ? C30 H30A 0.935(19) . ? C31 C32 1.400(3) . ? C31 H31A 0.954(19) . ? C32 H32A 0.966(18) . ? 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 C19 O1 C21 117.44(14) . . ? C11 N1 N3 106.42(12) . . ? C11 N1 H1AA 126.8 . . ? N3 N1 H1AA 126.8 . . ? C24 N2 C11 111.63(14) . . ? C9 N3 N1 110.90(12) . . ? C9 N3 C6 126.12(13) . . ? N1 N3 C6 119.20(13) . . ? C2 C1 C6 119.30(17) . . ? C2 C1 H1A 118.6(11) . . ? C6 C1 H1A 122.0(11) . . ? C3 C2 C1 120.12(17) . . ? C3 C2 H2A 120.2(12) . . ? C1 C2 H2A 119.7(12) . . ? C4 C3 C2 120.30(16) . . ? C4 C3 H3A 121.1(11) . . ? C2 C3 H3A 118.6(11) . . ? C3 C4 C5 120.19(17) . . ? C3 C4 H4A 120.0(10) . . ? C5 C4 H4A 119.8(10) . . ? C6 C5 C4 119.36(16) . . ? C6 C5 H5A 118.9(12) . . ? C4 C5 H5A 121.5(12) . . ? C5 C6 C1 120.70(15) . . ? C5 C6 N3 120.54(14) . . ? C1 C6 N3 118.75(15) . . ? O3 C9 N3 123.55(15) . . ? O3 C9 C13 131.12(15) . . ? N3 C9 C13 105.28(13) . . ? N2 C11 N1 122.31(14) . . ? N2 C11 C13 126.87(14) . . ? N1 C11 C13 110.81(13) . . ? C15 C12 C24 120.24(14) . . ? C15 C12 C27 132.43(15) . . ? C24 C12 C27 107.09(13) . . ? C11 C13 C15 120.47(14) . . ? C11 C13 C9 106.03(14) . . ? C15 C13 C9 133.34(14) . . ? C12 C15 C13 113.65(14) . . ? C12 C15 C16 125.31(14) . . ? C13 C15 C16 121.01(14) . . ? C23 C16 C17 118.60(15) . . ? C23 C16 C15 122.19(14) . . ? C17 C16 C15 119.21(14) . . ? C18 C17 C16 120.65(15) . . ? C18 C17 H17A 118.8(9) . . ? C16 C17 H17A 120.5(9) . . ? C17 C18 C19 120.10(15) . . ? C17 C18 H18A 118.3(10) . . ? C19 C18 H18A 121.5(10) . . ? O1 C19 C18 115.08(14) . . ? O1 C19 C22 124.78(15) . . ? C18 C19 C22 120.12(15) . . ? O1 C21 H21A 103.0(14) . . ? O1 C21 H21B 111.3(11) . . ? H21A C21 H21B 114.0(18) . . ? O1 C21 H21C 112.4(12) . . ? H21A C21 H21C 104.5(18) . . ? H21B C21 H21C 111.2(16) . . ? C19 C22 C23 119.31(15) . . ? C19 C22 H22A 122.0(11) . . ? C23 C22 H22A 118.6(11) . . ? C22 C23 C16 121.21(15) . . ? C22 C23 H23A 119.7(10) . . ? C16 C23 H23A 119.1(10) . . ? N2 C24 C12 127.05(14) . . ? N2 C24 C25 123.56(14) . . ? C12 C24 C25 109.38(13) . . ? C29 C25 C26 120.91(15) . . ? C29 C25 C24 130.56(15) . . ? C26 C25 C24 108.53(14) . . ? C32 C26 C25 121.30(16) . . ? C32 C26 C27 129.69(16) . . ? C25 C26 C27 109.01(13) . . ? O2 C27 C26 125.47(15) . . ? O2 C27 C12 128.51(15) . . ? C26 C27 C12 105.97(13) . . ? C25 C29 C30 117.97(16) . . ? C25 C29 H29A 120.5(10) . . ? C30 C29 H29A 121.6(10) . . ? C29 C30 C31 121.21(17) . . ? C29 C30 H30A 121.5(11) . . ? C31 C30 H30A 117.2(11) . . ? C30 C31 C32 120.81(16) . . ? C30 C31 H31A 119.8(11) . . ? C32 C31 H31A 119.3(11) . . ? C26 C32 C31 117.79(16) . . ? C26 C32 H32A 120.5(10) . . ? C31 C32 H32A 121.7(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 N3 C9 -7.58(17) . . . . ? C11 N1 N3 C6 -167.02(13) . . . . ? C6 C1 C2 C3 -1.3(3) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 1.0(3) . . . . ? C3 C4 C5 C6 -0.6(2) . . . . ? C4 C5 C6 C1 -0.8(2) . . . . ? C4 C5 C6 N3 178.52(15) . . . . ? C2 C1 C6 C5 1.7(3) . . . . ? C2 C1 C6 N3 -177.56(16) . . . . ? C9 N3 C6 C5 -134.90(17) . . . . ? N1 N3 C6 C5 21.1(2) . . . . ? C9 N3 C6 C1 44.4(2) . . . . ? N1 N3 C6 C1 -159.58(15) . . . . ? N1 N3 C9 O3 -170.34(15) . . . . ? C6 N3 C9 O3 -12.6(3) . . . . ? N1 N3 C9 C13 7.35(18) . . . . ? C6 N3 C9 C13 165.05(14) . . . . ? C24 N2 C11 N1 -175.86(14) . . . . ? C24 N2 C11 C13 2.8(2) . . . . ? N3 N1 C11 N2 -176.53(14) . . . . ? N3 N1 C11 C13 4.59(17) . . . . ? N2 C11 C13 C15 -3.1(2) . . . . ? N1 C11 C13 C15 175.76(14) . . . . ? N2 C11 C13 C9 -179.01(15) . . . . ? N1 C11 C13 C9 -0.19(18) . . . . ? O3 C9 C13 C11 173.12(18) . . . . ? N3 C9 C13 C11 -4.33(17) . . . . ? O3 C9 C13 C15 -2.1(3) . . . . ? N3 C9 C13 C15 -179.53(17) . . . . ? C24 C12 C15 C13 1.9(2) . . . . ? C27 C12 C15 C13 175.58(16) . . . . ? C24 C12 C15 C16 -175.88(14) . . . . ? C27 C12 C15 C16 -2.2(3) . . . . ? C11 C13 C15 C12 0.4(2) . . . . ? C9 C13 C15 C12 175.01(17) . . . . ? C11 C13 C15 C16 178.28(14) . . . . ? C9 C13 C15 C16 -7.1(3) . . . . ? C12 C15 C16 C23 -47.7(2) . . . . ? C13 C15 C16 C23 134.64(17) . . . . ? C12 C15 C16 C17 133.19(17) . . . . ? C13 C15 C16 C17 -44.5(2) . . . . ? C23 C16 C17 C18 0.7(2) . . . . ? C15 C16 C17 C18 179.88(15) . . . . ? C16 C17 C18 C19 -1.2(2) . . . . ? C21 O1 C19 C18 177.39(16) . . . . ? C21 O1 C19 C22 -4.5(2) . . . . ? C17 C18 C19 O1 178.65(15) . . . . ? C17 C18 C19 C22 0.4(3) . . . . ? O1 C19 C22 C23 -177.31(15) . . . . ? C18 C19 C22 C23 0.7(3) . . . . ? C19 C22 C23 C16 -1.2(3) . . . . ? C17 C16 C23 C22 0.4(2) . . . . ? C15 C16 C23 C22 -178.68(15) . . . . ? C11 N2 C24 C12 -0.2(2) . . . . ? C11 N2 C24 C25 -178.68(14) . . . . ? C15 C12 C24 N2 -2.2(2) . . . . ? C27 C12 C24 N2 -177.31(15) . . . . ? C15 C12 C24 C25 176.44(14) . . . . ? C27 C12 C24 C25 1.35(17) . . . . ? N2 C24 C25 C29 -2.2(3) . . . . ? C12 C24 C25 C29 179.13(16) . . . . ? N2 C24 C25 C26 177.97(14) . . . . ? C12 C24 C25 C26 -0.74(17) . . . . ? C29 C25 C26 C32 0.0(2) . . . . ? C24 C25 C26 C32 179.86(14) . . . . ? C29 C25 C26 C27 179.92(14) . . . . ? C24 C25 C26 C27 -0.19(17) . . . . ? C32 C26 C27 O2 3.4(3) . . . . ? C25 C26 C27 O2 -176.57(15) . . . . ? C32 C26 C27 C12 -179.07(16) . . . . ? C25 C26 C27 C12 0.99(17) . . . . ? C15 C12 C27 O2 1.8(3) . . . . ? C24 C12 C27 O2 176.04(16) . . . . ? C15 C12 C27 C26 -175.68(16) . . . . ? C24 C12 C27 C26 -1.42(16) . . . . ? C26 C25 C29 C30 0.3(2) . . . . ? C24 C25 C29 C30 -179.56(16) . . . . ? C25 C29 C30 C31 -0.4(3) . . . . ? C29 C30 C31 C32 0.2(3) . . . . ? C25 C26 C32 C31 -0.2(2) . . . . ? C27 C26 C32 C31 179.90(16) . . . . ? C30 C31 C32 C26 0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.466 _refine_diff_density_min -0.522 _refine_diff_density_rms 0.050