# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Francois Diederich' _publ_contact_author_address ; Laboratorium fur Organische Chemie ETH-Hoenggerberg HCI G 313 Wolfgang-Pauli-Strasse 10 Zurich CH 8093 SWITZERLAND ; _publ_contact_author_email DIEDERICH@ORG.CHEM.ETHZ.CH _publ_section_title ; A new class of organic donor-acceptor molecules with large third-order optical nonlinearities ; loop_ _publ_author_name 'Francois Diederich' 'Ivan Biaggio' 'Corinne Boudon' 'Jean-Paul Gisselbrecht' 'Maurice Gross' ; J.H.Lim ; 'Joshua C. May' 'Tsuyoshi Michinobu' 'Paul Seiler' data_michi4_D_04 _database_code_depnum_ccdc_archive 'CCDC 256337' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H11 N5' _chemical_formula_sum 'C16 H11 N5' _chemical_formula_weight 273.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7459(2) _cell_length_b 11.0754(3) _cell_length_c 15.1601(5) _cell_angle_alpha 70.935(1) _cell_angle_beta 71.461(1) _cell_angle_gamma 61.437(2) _cell_volume 1469.05(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6024 _cell_measurement_theta_min 3.68 _cell_measurement_theta_max 27.45 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 11122 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 27.45 _reflns_number_total 6573 _reflns_number_gt 5258 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo + Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et Al., 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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^)+(0.0000P)^2^+0.7740P] 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 'H-atoms riding' _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.015(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6573 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0612 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1050 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_restrained_S_all 0.899 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.77096(14) 0.18089(13) 1.03019(9) 0.0308(3) Uani 1 d . . . C2 C 0.69013(14) 0.12915(14) 1.11379(9) 0.0320(3) Uani 1 d . . . H2A H 0.6628 0.1661 1.1688 0.034(4) Uiso 1 calc R . . C3 C 0.65006(14) 0.02712(14) 1.11757(10) 0.0338(3) Uani 1 d . . . H3A H 0.5937 -0.0037 1.1745 0.037(4) Uiso 1 calc R . . C4 C 0.69136(14) -0.03325(13) 1.03778(10) 0.0328(3) Uani 1 d . . . C5 C 0.76626(15) 0.02346(14) 0.95246(10) 0.0364(3) Uani 1 d . . . H5A H 0.7905 -0.0107 0.8966 0.048(5) Uiso 1 calc R . . C6 C 0.80447(15) 0.12722(14) 0.94917(10) 0.0354(3) Uani 1 d . . . H6A H 0.8546 0.1634 0.8910 0.032(4) Uiso 1 calc R . . N7 N 0.65869(13) -0.13988(12) 1.04329(9) 0.0400(3) Uani 1 d . . . C8 C 0.60350(18) -0.21245(17) 1.13464(12) 0.0478(4) Uani 1 d . . . H8A H 0.6665 -0.2418 1.1793 0.072 Uiso 1 calc R . . H8B H 0.6013 -0.2954 1.1262 0.072 Uiso 1 calc R . . H8C H 0.5056 -0.1490 1.1599 0.072 Uiso 1 calc R . . C9 C 0.69531(18) -0.19933(16) 0.96116(12) 0.0474(4) Uani 1 d . . . H9A H 0.6700 -0.1232 0.9054 0.071 Uiso 1 calc R . . H9B H 0.6414 -0.2558 0.9739 0.071 Uiso 1 calc R . . H9C H 0.7992 -0.2590 0.9488 0.071 Uiso 1 calc R . . C10 C 0.82158(13) 0.28138(13) 1.02932(9) 0.0314(3) Uani 1 d . . . C11 C 0.86687(14) 0.27728(14) 1.10612(10) 0.0333(3) Uani 1 d . . . C12 C 0.89720(15) 0.15872(15) 1.18405(10) 0.0365(3) Uani 1 d . . . N13 N 0.93112(16) 0.06208(15) 1.24460(10) 0.0502(3) Uani 1 d . . . C14 C 0.89533(15) 0.38892(15) 1.11047(11) 0.0379(3) Uani 1 d . . . N15 N 0.91916(16) 0.47719(15) 1.11447(11) 0.0530(3) Uani 1 d . . . C16 C 0.83119(15) 0.39045(14) 0.94409(10) 0.0344(3) Uani 1 d . . . H16A H 0.9109 0.4138 0.9295 0.040(4) Uiso 1 calc R . . C17 C 0.73663(15) 0.46009(14) 0.88500(10) 0.0354(3) Uani 1 d . . . C18 C 0.60514(16) 0.44640(14) 0.89773(10) 0.0362(3) Uani 1 d . . . N19 N 0.49592(15) 0.44638(14) 0.90375(10) 0.0477(3) Uani 1 d . . . C20 C 0.76015(19) 0.56398(17) 0.80267(11) 0.0489(4) Uani 1 d . . . N21 N 0.7776(2) 0.64594(19) 0.73791(13) 0.0826(6) Uani 1 d . . . C1' C 0.96726(14) 0.30206(14) 0.55703(10) 0.0329(3) Uani 1 d . . . C2' C 0.86218(14) 0.29529(15) 0.63941(10) 0.0362(3) Uani 1 d . . . H2'A H 0.8898 0.2238 0.6940 0.045(4) Uiso 1 calc R . . C3' C 0.71999(15) 0.38994(16) 0.64288(10) 0.0397(3) Uani 1 d . . . H3'A H 0.6508 0.3818 0.6993 0.039(4) Uiso 1 calc R . . C4' C 0.67506(14) 0.49938(14) 0.56354(11) 0.0373(3) Uani 1 d . . . C5' C 0.78112(15) 0.50470(14) 0.48049(11) 0.0379(3) Uani 1 d . . . H5'A H 0.7542 0.5762 0.4258 0.051(5) Uiso 1 calc R . . C6' C 0.92299(15) 0.40805(14) 0.47728(10) 0.0363(3) Uani 1 d . . . H6'A H 0.9920 0.4132 0.4202 0.034(4) Uiso 1 calc R . . N7' N 0.53427(13) 0.59380(14) 0.56717(10) 0.0472(3) Uani 1 d . . . C8' C 0.43008(18) 0.5980(2) 0.65593(13) 0.0646(5) Uani 1 d . . . H8'A H 0.4175 0.5102 0.6779 0.097 Uiso 1 calc R . . H8'B H 0.3373 0.6775 0.6460 0.097 Uiso 1 calc R . . H8'C H 0.4649 0.6093 0.7039 0.097 Uiso 1 calc R . . C9' C 0.48854(18) 0.70427(18) 0.48460(13) 0.0550(4) Uani 1 d . . . H9'A H 0.5303 0.7711 0.4726 0.082 Uiso 1 calc R . . H9'B H 0.3829 0.7535 0.4968 0.082 Uiso 1 calc R . . H9'C H 0.5216 0.6625 0.4289 0.082 Uiso 1 calc R . . C10' C 1.11777(13) 0.20019(13) 0.55304(9) 0.0320(3) Uani 1 d . . . C11' C 1.18725(14) 0.15529(14) 0.62719(10) 0.0338(3) Uani 1 d . . . C12' C 1.12537(15) 0.21654(16) 0.70955(11) 0.0399(3) Uani 1 d . . . N13' N 1.08106(15) 0.26566(16) 0.77522(11) 0.0560(4) Uani 1 d . . . C14' C 1.32835(14) 0.04158(15) 0.62756(10) 0.0377(3) Uani 1 d . . . N15' N 1.44197(13) -0.04864(15) 0.62701(10) 0.0508(3) Uani 1 d . . . C16' C 1.20004(14) 0.13831(14) 0.46943(10) 0.0347(3) Uani 1 d . . . H16B H 1.3008 0.1143 0.4533 0.040(4) Uiso 1 calc R . . C17' C 1.14386(15) 0.11277(14) 0.41353(10) 0.0359(3) Uani 1 d . . . C18' C 0.99432(16) 0.14131(15) 0.42705(10) 0.0393(3) Uani 1 d . . . N19' N 0.87871(15) 0.15641(15) 0.43466(11) 0.0526(3) Uani 1 d . . . C20' C 1.23656(18) 0.04271(18) 0.33647(11) 0.0476(4) Uani 1 d . . . N21' N 1.3078(2) -0.0150(2) 0.27629(12) 0.0747(5) Uani 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 0.0317(6) 0.0275(6) 0.0325(6) -0.0055(5) -0.0064(5) -0.0121(5) C2 0.0330(6) 0.0333(7) 0.0317(6) -0.0066(5) -0.0075(5) -0.0146(5) C3 0.0326(6) 0.0340(7) 0.0355(7) -0.0043(5) -0.0067(5) -0.0164(6) C4 0.0303(6) 0.0268(6) 0.0420(7) -0.0062(5) -0.0126(5) -0.0097(5) C5 0.0399(7) 0.0328(7) 0.0367(7) -0.0107(6) -0.0088(6) -0.0125(6) C6 0.0387(7) 0.0335(7) 0.0318(7) -0.0059(5) -0.0042(5) -0.0158(6) N7 0.0428(7) 0.0329(6) 0.0500(7) -0.0106(5) -0.0114(5) -0.0175(5) C8 0.0487(9) 0.0395(8) 0.0610(10) -0.0145(7) -0.0018(7) -0.0259(7) C9 0.0513(9) 0.0384(8) 0.0606(10) -0.0176(7) -0.0156(7) -0.0175(7) C10 0.0268(6) 0.0295(6) 0.0354(7) -0.0088(5) -0.0019(5) -0.0111(5) C11 0.0307(6) 0.0315(6) 0.0380(7) -0.0079(5) -0.0054(5) -0.0137(5) C12 0.0365(7) 0.0392(7) 0.0391(7) -0.0091(6) -0.0087(6) -0.0185(6) N13 0.0588(8) 0.0487(8) 0.0490(8) 0.0000(6) -0.0216(6) -0.0267(7) C14 0.0335(7) 0.0387(7) 0.0434(8) -0.0100(6) -0.0065(6) -0.0164(6) N15 0.0548(8) 0.0523(8) 0.0649(9) -0.0192(7) -0.0076(7) -0.0306(7) C16 0.0347(7) 0.0341(7) 0.0363(7) -0.0090(5) -0.0002(5) -0.0189(6) C17 0.0416(7) 0.0312(7) 0.0316(7) -0.0048(5) -0.0030(5) -0.0176(6) C18 0.0431(8) 0.0316(7) 0.0314(7) -0.0054(5) -0.0079(6) -0.0142(6) N19 0.0488(8) 0.0457(7) 0.0520(8) -0.0102(6) -0.0157(6) -0.0187(6) C20 0.0609(10) 0.0427(8) 0.0401(8) -0.0022(7) -0.0052(7) -0.0265(8) N21 0.1111(15) 0.0651(11) 0.0570(10) 0.0152(8) -0.0072(10) -0.0490(11) C1' 0.0284(6) 0.0300(6) 0.0357(7) -0.0066(5) -0.0065(5) -0.0088(5) C2' 0.0301(6) 0.0387(7) 0.0334(7) -0.0063(6) -0.0073(5) -0.0094(6) C3' 0.0289(7) 0.0453(8) 0.0365(7) -0.0107(6) -0.0042(5) -0.0090(6) C4' 0.0298(6) 0.0333(7) 0.0451(8) -0.0116(6) -0.0103(6) -0.0064(5) C5' 0.0363(7) 0.0283(6) 0.0425(8) -0.0030(6) -0.0114(6) -0.0090(6) C6' 0.0328(7) 0.0316(7) 0.0374(7) -0.0040(6) -0.0045(5) -0.0114(6) N7' 0.0315(6) 0.0444(7) 0.0494(8) -0.0093(6) -0.0117(5) -0.0013(5) C8' 0.0326(8) 0.0735(12) 0.0546(10) -0.0166(9) -0.0071(7) 0.0046(8) C9' 0.0379(8) 0.0413(9) 0.0655(11) -0.0017(8) -0.0164(7) -0.0031(7) C10' 0.0272(6) 0.0289(6) 0.0344(7) -0.0034(5) -0.0037(5) -0.0111(5) C11' 0.0269(6) 0.0323(7) 0.0364(7) -0.0063(5) -0.0037(5) -0.0099(5) C12' 0.0306(7) 0.0401(8) 0.0436(8) -0.0082(6) -0.0104(6) -0.0090(6) N13' 0.0453(8) 0.0636(9) 0.0575(9) -0.0280(7) -0.0122(6) -0.0105(7) C14' 0.0295(7) 0.0420(8) 0.0350(7) -0.0061(6) -0.0047(5) -0.0121(6) N15' 0.0316(6) 0.0549(8) 0.0474(8) -0.0091(6) -0.0070(5) -0.0050(6) C16' 0.0275(6) 0.0325(7) 0.0337(7) -0.0022(5) -0.0012(5) -0.0104(5) C17' 0.0338(7) 0.0326(7) 0.0317(7) -0.0039(5) -0.0027(5) -0.0106(6) C18' 0.0389(8) 0.0353(7) 0.0385(7) -0.0062(6) -0.0108(6) -0.0104(6) N19' 0.0409(7) 0.0490(8) 0.0657(9) -0.0130(7) -0.0188(6) -0.0113(6) C20' 0.0467(9) 0.0494(9) 0.0391(8) -0.0119(7) -0.0027(7) -0.0159(7) N21' 0.0755(11) 0.0809(12) 0.0574(10) -0.0345(9) 0.0074(8) -0.0246(9) _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 C6 1.4081(19) . ? C1 C2 1.4109(18) . ? C1 C10 1.4490(18) . ? C2 C3 1.3686(18) . ? C3 C4 1.4177(19) . ? C4 N7 1.3559(17) . ? C4 C5 1.4163(19) . ? C5 C6 1.3756(19) . ? N7 C9 1.454(2) . ? N7 C8 1.457(2) . ? C10 C11 1.3781(19) . ? C10 C16 1.4677(18) . ? C11 C12 1.431(2) . ? C11 C14 1.4333(19) . ? C12 N13 1.1484(19) . ? C14 N15 1.1459(19) . ? C16 C17 1.345(2) . ? C17 C18 1.438(2) . ? C17 C20 1.444(2) . ? C18 N19 1.1479(19) . ? C20 N21 1.134(2) . ? C1' C2' 1.4012(19) . ? C1' C6' 1.4038(19) . ? C1' C10' 1.4594(17) . ? C2' C3' 1.3746(18) . ? C3' C4' 1.416(2) . ? C4' N7' 1.3628(17) . ? C4' C5' 1.411(2) . ? C5' C6' 1.3779(19) . ? N7' C8' 1.449(2) . ? N7' C9' 1.456(2) . ? C10' C11' 1.3717(19) . ? C10' C16' 1.4606(19) . ? C11' C12' 1.434(2) . ? C11' C14' 1.4353(18) . ? C12' N13' 1.148(2) . ? C14' N15' 1.1496(18) . ? C16' C17' 1.345(2) . ? C17' C18' 1.439(2) . ? C17' C20' 1.439(2) . ? C18' N19' 1.1434(19) . ? C20' N21' 1.138(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 C6 C1 C2 117.34(12) . . ? C6 C1 C10 121.65(12) . . ? C2 C1 C10 120.97(12) . . ? C3 C2 C1 121.66(12) . . ? C2 C3 C4 121.04(12) . . ? N7 C4 C5 121.74(13) . . ? N7 C4 C3 120.98(13) . . ? C5 C4 C3 117.28(12) . . ? C6 C5 C4 121.04(13) . . ? C5 C6 C1 121.44(13) . . ? C4 N7 C9 121.68(13) . . ? C4 N7 C8 120.97(12) . . ? C9 N7 C8 116.82(12) . . ? C11 C10 C1 122.37(12) . . ? C11 C10 C16 116.84(12) . . ? C1 C10 C16 120.77(12) . . ? C10 C11 C12 122.77(12) . . ? C10 C11 C14 121.88(12) . . ? C12 C11 C14 115.24(12) . . ? N13 C12 C11 175.40(15) . . ? N15 C14 C11 179.30(17) . . ? C17 C16 C10 125.45(12) . . ? C16 C17 C18 125.81(12) . . ? C16 C17 C20 119.74(13) . . ? C18 C17 C20 114.38(13) . . ? N19 C18 C17 174.48(15) . . ? N21 C20 C17 179.5(2) . . ? C2' C1' C6' 118.01(12) . . ? C2' C1' C10' 121.25(12) . . ? C6' C1' C10' 120.72(12) . . ? C3' C2' C1' 121.34(13) . . ? C2' C3' C4' 121.01(13) . . ? N7' C4' C5' 121.62(13) . . ? N7' C4' C3' 121.02(13) . . ? C5' C4' C3' 117.35(12) . . ? C6' C5' C4' 121.18(13) . . ? C5' C6' C1' 121.08(13) . . ? C4' N7' C8' 121.00(13) . . ? C4' N7' C9' 120.63(13) . . ? C8' N7' C9' 117.94(13) . . ? C11' C10' C1' 122.39(12) . . ? C11' C10' C16' 117.00(12) . . ? C1' C10' C16' 120.59(12) . . ? C10' C11' C12' 123.14(12) . . ? C10' C11' C14' 121.69(13) . . ? C12' C11' C14' 115.17(12) . . ? N13' C12' C11' 177.23(16) . . ? N15' C14' C11' 179.26(18) . . ? C17' C16' C10' 124.93(12) . . ? C16' C17' C18' 125.38(13) . . ? C16' C17' C20' 120.28(13) . . ? C18' C17' C20' 114.21(13) . . ? N19' C18' C17' 175.17(16) . . ? N21' C20' C17' 178.10(19) . . ? 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 C6 C1 C2 C3 2.36(19) . . . . ? C10 C1 C2 C3 -175.43(12) . . . . ? C1 C2 C3 C4 1.5(2) . . . . ? C2 C3 C4 N7 176.20(12) . . . . ? C2 C3 C4 C5 -4.50(19) . . . . ? N7 C4 C5 C6 -176.98(13) . . . . ? C3 C4 C5 C6 3.72(19) . . . . ? C4 C5 C6 C1 0.1(2) . . . . ? C2 C1 C6 C5 -3.1(2) . . . . ? C10 C1 C6 C5 174.64(13) . . . . ? C5 C4 N7 C9 -1.7(2) . . . . ? C3 C4 N7 C9 177.58(13) . . . . ? C5 C4 N7 C8 169.72(13) . . . . ? C3 C4 N7 C8 -11.00(19) . . . . ? C6 C1 C10 C11 -141.61(14) . . . . ? C2 C1 C10 C11 36.09(19) . . . . ? C6 C1 C10 C16 36.36(18) . . . . ? C2 C1 C10 C16 -145.94(13) . . . . ? C1 C10 C11 C12 13.8(2) . . . . ? C16 C10 C11 C12 -164.28(12) . . . . ? C1 C10 C11 C14 -170.13(12) . . . . ? C16 C10 C11 C14 11.83(19) . . . . ? C10 C11 C12 N13 112.0(19) . . . . ? C14 C11 C12 N13 -64.3(19) . . . . ? C10 C11 C14 N15 -148(16) . . . . ? C12 C11 C14 N15 29(16) . . . . ? C11 C10 C16 C17 -144.32(14) . . . . ? C1 C10 C16 C17 37.6(2) . . . . ? C10 C16 C17 C18 4.0(2) . . . . ? C10 C16 C17 C20 -179.17(13) . . . . ? C16 C17 C18 N19 152.6(16) . . . . ? C20 C17 C18 N19 -24.4(17) . . . . ? C16 C17 C20 N21 -167(100) . . . . ? C18 C17 C20 N21 11(23) . . . . ? C6' C1' C2' C3' -0.5(2) . . . . ? C10' C1' C2' C3' -179.07(13) . . . . ? C1' C2' C3' C4' -1.1(2) . . . . ? C2' C3' C4' N7' -179.55(14) . . . . ? C2' C3' C4' C5' 1.7(2) . . . . ? N7' C4' C5' C6' -179.47(14) . . . . ? C3' C4' C5' C6' -0.7(2) . . . . ? C4' C5' C6' C1' -0.9(2) . . . . ? C2' C1' C6' C5' 1.5(2) . . . . ? C10' C1' C6' C5' -179.95(13) . . . . ? C5' C4' N7' C8' -172.35(16) . . . . ? C3' C4' N7' C8' 8.9(2) . . . . ? C5' C4' N7' C9' 0.0(2) . . . . ? C3' C4' N7' C9' -178.75(15) . . . . ? C2' C1' C10' C11' -41.7(2) . . . . ? C6' C1' C10' C11' 139.85(14) . . . . ? C2' C1' C10' C16' 136.56(14) . . . . ? C6' C1' C10' C16' -41.92(19) . . . . ? C1' C10' C11' C12' -8.1(2) . . . . ? C16' C10' C11' C12' 173.57(13) . . . . ? C1' C10' C11' C14' 171.43(13) . . . . ? C16' C10' C11' C14' -6.87(19) . . . . ? C10' C11' C12' N13' -135(3) . . . . ? C14' C11' C12' N13' 46(4) . . . . ? C10' C11' C14' N15' 65(15) . . . . ? C12' C11' C14' N15' -116(15) . . . . ? C11' C10' C16' C17' 146.52(14) . . . . ? C1' C10' C16' C17' -31.8(2) . . . . ? C10' C16' C17' C18' -0.4(2) . . . . ? C10' C16' C17' C20' -175.84(13) . . . . ? C16' C17' C18' N19' -152.3(19) . . . . ? C20' C17' C18' N19' 23(2) . . . . ? C16' C17' C20' N21' 135(6) . . . . ? C18' C17' C20' N21' -41(6) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.186 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.032 data_michi6_D_04 _database_code_depnum_ccdc_archive 'CCDC 256338' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 N6,2(CH2 Cl2)' _chemical_formula_sum 'C28 H24 Cl4 N6' _chemical_formula_weight 586.33 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' Cl Cl 0.1484 0.1585 '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 7.3661(1) _cell_length_b 9.5653(2) _cell_length_c 20.8690(4) _cell_angle_alpha 91.580(8) _cell_angle_beta 95.014(7) _cell_angle_gamma 92.986(9) _cell_volume 1462.03(5) _cell_formula_units_Z 2 _cell_measurement_temperature 263(2) _cell_measurement_reflns_used 2993 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 20.81 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.433 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 263(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 3850 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 20.81 _reflns_number_total 2595 _reflns_number_gt 2223 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo + Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et Al., 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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^)+(0.0928P)^2^+6.8860P] 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 'H-atoms riding' _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.014(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2595 _refine_ls_number_parameters 348 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1135 _refine_ls_R_factor_gt 0.1005 _refine_ls_wR_factor_ref 0.2448 _refine_ls_wR_factor_gt 0.2350 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.002 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0329(9) 0.1493(9) 0.2648(3) 0.050(2) Uani 1 d . . . C2 C 0.0866(10) 0.2225(9) 0.2120(4) 0.054(2) Uani 1 d . . . C3 C 0.1242(10) 0.2775(9) 0.1647(4) 0.054(2) Uani 1 d . . . C4 C 0.1659(10) 0.3452(10) 0.1071(3) 0.055(2) Uani 1 d . . . C5 C 0.2223(10) 0.4860(10) 0.1050(4) 0.062(2) Uani 1 d . . . H5A H 0.2368 0.5399 0.1430 0.075 Uiso 1 calc R . . C6 C 0.2567(10) 0.5470(10) 0.0490(4) 0.059(2) Uani 1 d . . . H6A H 0.2923 0.6417 0.0490 0.070 Uiso 1 calc R . . C7 C 0.2385(10) 0.4671(10) -0.0092(4) 0.059(2) Uani 1 d . . . C8 C 0.1810(10) 0.3231(9) -0.0080(4) 0.054(2) Uani 1 d . . . H8A H 0.1674 0.2685 -0.0459 0.065 Uiso 1 calc R . . C9 C 0.1463(9) 0.2660(9) 0.0483(4) 0.055(2) Uani 1 d . . . H9A H 0.1084 0.1717 0.0486 0.065 Uiso 1 calc R . . N10 N 0.2726(8) 0.5284(8) -0.0658(3) 0.064(2) Uani 1 d . . . C11 C 0.3295(11) 0.6758(10) -0.0682(4) 0.073(3) Uani 1 d . . . H11A H 0.2454 0.7312 -0.0474 0.109 Uiso 1 calc R . . H11B H 0.3312 0.7017 -0.1123 0.109 Uiso 1 calc R . . H11C H 0.4495 0.6918 -0.0466 0.109 Uiso 1 calc R . . C12 C 0.2558(12) 0.4475(11) -0.1271(4) 0.078(3) Uani 1 d . . . H12A H 0.3195 0.3629 -0.1219 0.117 Uiso 1 calc R . . H12B H 0.3078 0.5023 -0.1595 0.117 Uiso 1 calc R . . H12C H 0.1293 0.4245 -0.1400 0.117 Uiso 1 calc R . . C13 C 0.0364(10) 0.2308(8) 0.3282(3) 0.050(2) Uani 1 d . . . C14 C 0.1939(10) 0.2236(8) 0.3730(3) 0.048(2) Uani 1 d . . . C15 C 0.2213(11) 0.2953(10) 0.4324(4) 0.063(2) Uani 1 d . . . H15A H 0.1332 0.3551 0.4439 0.076 Uiso 1 calc R . . C16 C 0.3698(11) 0.2819(10) 0.4737(4) 0.068(3) Uani 1 d . . . H16A H 0.3808 0.3334 0.5125 0.082 Uiso 1 calc R . . C17 C 0.5081(10) 0.1932(10) 0.4605(4) 0.059(2) Uani 1 d . . . C18 C 0.4857(10) 0.1208(9) 0.4012(4) 0.055(2) Uani 1 d . . . H18A H 0.5748 0.0619 0.3896 0.066 Uiso 1 calc R . . C19 C 0.3343(10) 0.1355(9) 0.3599(4) 0.056(2) Uani 1 d . . . H19A H 0.3232 0.0846 0.3210 0.068 Uiso 1 calc R . . N20 N 0.6550(9) 0.1798(8) 0.5017(3) 0.071(2) Uani 1 d . . . C21 C 0.6863(15) 0.2647(13) 0.5625(4) 0.103(4) Uani 1 d . . . H21A H 0.6813 0.3622 0.5533 0.155 Uiso 1 calc R . . H21B H 0.8041 0.2475 0.5833 0.155 Uiso 1 calc R . . H21C H 0.5937 0.2393 0.5904 0.155 Uiso 1 calc R . . C22 C 0.7994(11) 0.0860(12) 0.4889(4) 0.081(3) Uani 1 d . . . H22A H 0.7459 -0.0001 0.4693 0.121 Uiso 1 calc R . . H22B H 0.8681 0.0669 0.5287 0.121 Uiso 1 calc R . . H22C H 0.8790 0.1298 0.4605 0.121 Uiso 1 calc R . . C23 C -0.1155(11) 0.3052(9) 0.3336(3) 0.053(2) Uani 1 d . . . C24 C -0.2605(13) 0.2955(9) 0.2828(4) 0.066(2) Uani 1 d . . . N25 N -0.3787(11) 0.2878(9) 0.2426(4) 0.081(2) Uani 1 d . . . C26 C -0.1488(11) 0.3959(12) 0.3868(4) 0.072(3) Uani 1 d . . . N27 N -0.1820(11) 0.4643(11) 0.4282(4) 0.095(3) Uani 1 d . . . C28 C -0.0232(10) 0.0124(10) 0.2604(4) 0.059(2) Uani 1 d . . . C29 C -0.0791(11) -0.0623(10) 0.3162(5) 0.066(2) Uani 1 d . . . N30 N -0.1242(12) -0.1166(9) 0.3604(4) 0.087(3) Uani 1 d . . . C31 C -0.0309(12) -0.0673(11) 0.2005(5) 0.071(3) Uani 1 d . . . N32 N -0.0326(14) -0.1229(12) 0.1523(4) 0.112(3) Uani 1 d . . . C100 C 0.456(2) 0.0137(15) 0.1538(9) 0.167(7) Uani 1 d . . . H20A H 0.5467 0.0904 0.1634 0.200 Uiso 1 calc R . . H20B H 0.3370 0.0525 0.1532 0.200 Uiso 1 calc R . . Cl1 Cl 0.4744(5) -0.0929(5) 0.21064(18) 0.1479(16) Uani 1 d . . . Cl2 Cl 0.4826(9) -0.0551(5) 0.07476(19) 0.188(2) Uani 1 d . . . C200 C 0.3683(14) 0.5242(13) 0.2909(6) 0.106(4) Uani 1 d . . . H21D H 0.3668 0.4641 0.3276 0.127 Uiso 1 calc R . . H21E H 0.3759 0.4645 0.2530 0.127 Uiso 1 calc R . . Cl3 Cl 0.5606(4) 0.6331(4) 0.30114(19) 0.1289(13) Uani 1 d . . . Cl4 Cl 0.1639(4) 0.6056(3) 0.28258(14) 0.1075(11) Uani 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 0.047(4) 0.060(6) 0.043(5) 0.002(4) 0.000(3) 0.005(4) C2 0.054(5) 0.067(6) 0.042(5) -0.005(5) 0.007(4) 0.002(4) C3 0.050(5) 0.069(6) 0.042(5) -0.002(4) -0.004(4) 0.008(4) C4 0.046(4) 0.074(7) 0.044(5) 0.001(5) 0.004(3) -0.002(4) C5 0.056(5) 0.071(7) 0.060(6) 0.001(5) 0.006(4) -0.004(5) C6 0.056(5) 0.059(6) 0.060(6) -0.002(5) 0.003(4) -0.004(4) C7 0.045(4) 0.086(8) 0.045(5) 0.005(5) -0.001(4) 0.010(5) C8 0.055(5) 0.059(6) 0.045(5) -0.004(4) 0.000(4) -0.005(4) C9 0.049(4) 0.054(6) 0.060(6) 0.002(5) 0.005(4) -0.002(4) N10 0.060(4) 0.075(6) 0.057(5) 0.008(4) 0.005(3) -0.007(4) C11 0.067(5) 0.072(7) 0.077(6) 0.020(5) -0.005(4) -0.017(5) C12 0.084(6) 0.099(8) 0.051(5) 0.010(5) 0.013(4) 0.003(6) C13 0.055(5) 0.046(5) 0.049(5) 0.008(4) 0.008(4) 0.000(4) C14 0.049(4) 0.051(6) 0.045(5) 0.001(4) 0.007(4) 0.004(4) C15 0.053(5) 0.080(7) 0.057(5) -0.008(5) 0.008(4) 0.017(5) C16 0.061(5) 0.086(7) 0.056(5) -0.013(5) -0.001(4) 0.005(5) C17 0.048(5) 0.072(7) 0.054(5) 0.005(4) 0.000(4) -0.003(5) C18 0.054(5) 0.059(6) 0.055(5) -0.003(4) 0.009(4) 0.014(4) C19 0.060(5) 0.064(6) 0.046(5) 0.000(4) 0.008(4) 0.003(5) N20 0.067(5) 0.093(6) 0.052(4) -0.004(4) -0.001(4) 0.014(4) C21 0.116(8) 0.116(10) 0.070(7) -0.026(6) -0.036(6) 0.027(7) C22 0.062(5) 0.116(9) 0.066(6) 0.016(5) 0.005(4) 0.016(6) C23 0.065(5) 0.053(6) 0.041(5) 0.006(4) 0.004(4) 0.009(4) C24 0.068(6) 0.069(7) 0.064(6) 0.014(5) 0.022(5) 0.013(5) N25 0.069(5) 0.108(7) 0.067(5) 0.007(5) 0.003(4) 0.010(5) C26 0.061(6) 0.104(8) 0.052(6) 0.010(6) 0.002(4) 0.021(5) N27 0.092(6) 0.124(8) 0.071(6) -0.015(5) 0.013(5) 0.028(6) C28 0.059(5) 0.069(7) 0.049(5) 0.000(5) 0.006(4) -0.005(5) C29 0.067(6) 0.058(6) 0.070(6) -0.014(5) -0.003(5) 0.000(5) N30 0.114(7) 0.072(6) 0.072(5) 0.006(5) 0.009(5) -0.022(5) C31 0.071(6) 0.061(7) 0.078(7) -0.003(5) -0.001(5) -0.015(5) N32 0.142(8) 0.128(9) 0.064(6) -0.025(6) 0.013(5) -0.010(7) C100 0.141(11) 0.105(12) 0.28(2) 0.078(13) 0.087(12) 0.054(9) Cl1 0.143(3) 0.185(4) 0.121(3) 0.038(3) 0.027(2) 0.022(3) Cl2 0.330(7) 0.133(4) 0.108(3) -0.005(2) 0.046(3) 0.032(4) C200 0.093(7) 0.092(9) 0.128(9) -0.021(7) -0.009(6) 0.003(7) Cl3 0.108(2) 0.105(3) 0.172(3) 0.007(2) 0.012(2) -0.0089(19) Cl4 0.103(2) 0.109(3) 0.108(2) -0.0183(17) 0.0049(16) 0.0076(17) _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 C28 1.351(11) . ? C1 C2 1.396(12) . ? C1 C13 1.514(11) . ? C2 C3 1.178(11) . ? C3 C4 1.431(12) . ? C4 C5 1.392(11) . ? C4 C9 1.416(11) . ? C5 C6 1.358(11) . ? C6 C7 1.409(11) . ? C7 N10 1.371(10) . ? C7 C8 1.422(11) . ? C8 C9 1.349(10) . ? N10 C11 1.453(11) . ? N10 C12 1.469(11) . ? C13 C23 1.367(10) . ? C13 C14 1.431(10) . ? C14 C15 1.394(11) . ? C14 C19 1.407(10) . ? C15 C16 1.347(11) . ? C16 C17 1.401(11) . ? C17 N20 1.335(10) . ? C17 C18 1.395(11) . ? C18 C19 1.364(10) . ? N20 C22 1.464(11) . ? N20 C21 1.481(11) . ? C23 C24 1.434(13) . ? C23 C26 1.437(13) . ? C24 N25 1.153(11) . ? C26 N27 1.121(11) . ? C28 C31 1.440(14) . ? C28 C29 1.463(13) . ? C29 N30 1.137(11) . ? C31 N32 1.123(12) . ? C100 Cl1 1.587(14) . ? C100 Cl2 1.788(18) . ? C200 Cl3 1.709(11) . ? C200 Cl4 1.728(11) . ? 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 C28 C1 C2 122.4(7) . . ? C28 C1 C13 120.5(7) . . ? C2 C1 C13 117.1(8) . . ? C3 C2 C1 175.2(8) . . ? C2 C3 C4 178.8(8) . . ? C5 C4 C9 117.5(8) . . ? C5 C4 C3 123.8(7) . . ? C9 C4 C3 118.7(8) . . ? C6 C5 C4 121.9(8) . . ? C5 C6 C7 120.2(9) . . ? N10 C7 C6 120.3(9) . . ? N10 C7 C8 121.0(7) . . ? C6 C7 C8 118.7(8) . . ? C9 C8 C7 119.7(7) . . ? C8 C9 C4 122.0(8) . . ? C7 N10 C11 121.9(7) . . ? C7 N10 C12 121.5(8) . . ? C11 N10 C12 116.7(7) . . ? C23 C13 C14 128.9(7) . . ? C23 C13 C1 113.3(6) . . ? C14 C13 C1 117.8(6) . . ? C15 C14 C19 114.4(7) . . ? C15 C14 C13 125.1(7) . . ? C19 C14 C13 120.5(7) . . ? C16 C15 C14 122.9(7) . . ? C15 C16 C17 122.3(8) . . ? N20 C17 C18 121.6(7) . . ? N20 C17 C16 122.2(8) . . ? C18 C17 C16 116.2(7) . . ? C19 C18 C17 120.7(7) . . ? C18 C19 C14 123.5(7) . . ? C17 N20 C22 122.8(7) . . ? C17 N20 C21 121.7(7) . . ? C22 N20 C21 115.4(7) . . ? C13 C23 C24 119.7(7) . . ? C13 C23 C26 126.3(7) . . ? C24 C23 C26 114.0(7) . . ? N25 C24 C23 179.1(9) . . ? N27 C26 C23 177.1(11) . . ? C1 C28 C31 121.8(8) . . ? C1 C28 C29 121.6(7) . . ? C31 C28 C29 116.6(8) . . ? N30 C29 C28 177.9(10) . . ? N32 C31 C28 176.0(12) . . ? Cl1 C100 Cl2 116.6(9) . . ? Cl3 C200 Cl4 115.8(7) . . ? 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 C28 C1 C2 C3 25(10) . . . . ? C13 C1 C2 C3 -153(10) . . . . ? C1 C2 C3 C4 69(46) . . . . ? C2 C3 C4 C5 87(42) . . . . ? C2 C3 C4 C9 -92(42) . . . . ? C9 C4 C5 C6 0.4(11) . . . . ? C3 C4 C5 C6 -178.5(7) . . . . ? C4 C5 C6 C7 -1.0(11) . . . . ? C5 C6 C7 N10 179.8(7) . . . . ? C5 C6 C7 C8 1.0(11) . . . . ? N10 C7 C8 C9 -179.2(7) . . . . ? C6 C7 C8 C9 -0.4(10) . . . . ? C7 C8 C9 C4 -0.2(11) . . . . ? C5 C4 C9 C8 0.2(11) . . . . ? C3 C4 C9 C8 179.2(7) . . . . ? C6 C7 N10 C11 0.5(10) . . . . ? C8 C7 N10 C11 179.3(7) . . . . ? C6 C7 N10 C12 179.6(7) . . . . ? C8 C7 N10 C12 -1.6(11) . . . . ? C28 C1 C13 C23 -96.7(8) . . . . ? C2 C1 C13 C23 82.3(8) . . . . ? C28 C1 C13 C14 84.6(9) . . . . ? C2 C1 C13 C14 -96.4(8) . . . . ? C23 C13 C14 C15 -0.6(13) . . . . ? C1 C13 C14 C15 177.9(8) . . . . ? C23 C13 C14 C19 177.2(7) . . . . ? C1 C13 C14 C19 -4.3(11) . . . . ? C19 C14 C15 C16 0.1(12) . . . . ? C13 C14 C15 C16 178.0(8) . . . . ? C14 C15 C16 C17 -0.7(14) . . . . ? C15 C16 C17 N20 -179.8(9) . . . . ? C15 C16 C17 C18 1.2(13) . . . . ? N20 C17 C18 C19 179.7(8) . . . . ? C16 C17 C18 C19 -1.3(12) . . . . ? C17 C18 C19 C14 0.8(12) . . . . ? C15 C14 C19 C18 -0.2(11) . . . . ? C13 C14 C19 C18 -178.2(7) . . . . ? C18 C17 N20 C22 -1.9(13) . . . . ? C16 C17 N20 C22 179.2(8) . . . . ? C18 C17 N20 C21 175.2(9) . . . . ? C16 C17 N20 C21 -3.7(13) . . . . ? C14 C13 C23 C24 -178.9(8) . . . . ? C1 C13 C23 C24 2.5(10) . . . . ? C14 C13 C23 C26 0.8(14) . . . . ? C1 C13 C23 C26 -177.7(8) . . . . ? C13 C23 C24 N25 143(64) . . . . ? C26 C23 C24 N25 -37(64) . . . . ? C13 C23 C26 N27 -136(20) . . . . ? C24 C23 C26 N27 43(21) . . . . ? C2 C1 C28 C31 0.1(12) . . . . ? C13 C1 C28 C31 179.0(7) . . . . ? C2 C1 C28 C29 -179.9(7) . . . . ? C13 C1 C28 C29 -1.0(11) . . . . ? C1 C28 C29 N30 28(25) . . . . ? C31 C28 C29 N30 -152(25) . . . . ? C1 C28 C31 N32 4(16) . . . . ? C29 C28 C31 N32 -176(15) . . . . ? _diffrn_measured_fraction_theta_max 0.845 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 0.845 _refine_diff_density_max 0.406 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.055 data_michi8_D_04 _database_code_depnum_ccdc_archive 'CCDC 256339' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H20 N6' _chemical_formula_sum 'C24 H20 N6' _chemical_formula_weight 392.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M ' P b c a' 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 15.0448(7) _cell_length_b 15.9323(8) _cell_length_c 17.1300(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4106.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 4251 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 26.01 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 7171 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 26.01 _reflns_number_total 3962 _reflns_number_gt 2861 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo + Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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^)+(0.0452P)^2^+0.9961P] 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 'H-atoms riding' _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.0095(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3962 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1194 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.21297(12) -0.12634(10) 0.42292(9) 0.0321(4) Uani 1 d . . . C2 C 0.28107(12) -0.08844(10) 0.47006(10) 0.0318(4) Uani 1 d . . . C3 C 0.36420(12) -0.12627(11) 0.48612(11) 0.0367(4) Uani 1 d . . . H3A H 0.3789 -0.1770 0.4612 0.048(6) Uiso 1 calc R . . C4 C 0.42363(13) -0.09129(11) 0.53673(11) 0.0381(4) Uani 1 d . . . H4A H 0.4781 -0.1184 0.5459 0.048(6) Uiso 1 calc R . . C5 C 0.40465(12) -0.01443(11) 0.57587(10) 0.0354(4) Uani 1 d . . . C6 C 0.32409(13) 0.02597(11) 0.55616(10) 0.0367(4) Uani 1 d . . . H6A H 0.3109 0.0785 0.5782 0.040(5) Uiso 1 calc R . . C7 C 0.26512(12) -0.00999(11) 0.50569(10) 0.0346(4) Uani 1 d . . . H7A H 0.2120 0.0185 0.4943 0.033(5) Uiso 1 calc R . . N8 N 0.46161(11) 0.01864(10) 0.62902(9) 0.0424(4) Uani 1 d . . . C9 C 0.44575(16) 0.10100(13) 0.66277(13) 0.0512(5) Uani 1 d . . . H9A H 0.4442 0.1427 0.6216 0.061(7) Uiso 1 calc R . . H9B H 0.4931 0.1144 0.6991 0.074(7) Uiso 1 calc R . . H9C H 0.3893 0.1008 0.6901 0.075(8) Uiso 1 calc R . . C10 C 0.54202(14) -0.02516(14) 0.65193(13) 0.0503(5) Uani 1 d . . . H10A H 0.5280 -0.0832 0.6638 0.077(8) Uiso 1 calc R . . H10B H 0.5671 0.0015 0.6978 0.096(9) Uiso 1 calc R . . H10C H 0.5847 -0.0231 0.6095 0.068(7) Uiso 1 calc R . . C11 C 0.20873(12) -0.21045(11) 0.40218(10) 0.0355(4) Uani 1 d . . . C12 C 0.26119(14) -0.27436(11) 0.43829(11) 0.0401(5) Uani 1 d . . . N13 N 0.30039(13) -0.32577(11) 0.47036(11) 0.0531(5) Uani 1 d . . . C14 C 0.14245(14) -0.24020(12) 0.34863(11) 0.0412(5) Uani 1 d . . . N15 N 0.08919(13) -0.26367(11) 0.30589(11) 0.0559(5) Uani 1 d . . . C16 C 0.13599(12) -0.07256(10) 0.39691(10) 0.0322(4) Uani 1 d . . . C17 C 0.15298(12) -0.00448(10) 0.34318(9) 0.0315(4) Uani 1 d . . . C18 C 0.22948(12) -0.00588(11) 0.29547(10) 0.0357(4) Uani 1 d . . . H18A H 0.2687 -0.0516 0.2993 0.042(5) Uiso 1 calc R . . C19 C 0.24837(13) 0.05703(11) 0.24397(10) 0.0378(4) Uani 1 d . . . H19A H 0.2994 0.0531 0.2125 0.041(5) Uiso 1 calc R . . C20 C 0.19229(13) 0.12822(11) 0.23715(10) 0.0368(4) Uani 1 d . . . C21 C 0.11553(13) 0.13023(11) 0.28525(11) 0.0391(4) Uani 1 d . . . H21A H 0.0765 0.1762 0.2821 0.054(6) Uiso 1 calc R . . C22 C 0.09739(13) 0.06636(11) 0.33615(10) 0.0368(4) Uani 1 d . . . H22A H 0.0462 0.0698 0.3675 0.050(6) Uiso 1 calc R . . N23 N 0.21216(12) 0.19152(10) 0.18746(9) 0.0465(4) Uani 1 d . . . C24 C 0.29303(15) 0.19068(14) 0.14134(12) 0.0484(5) Uani 1 d . . . H24A H 0.3441 0.1933 0.1758 0.068(7) Uiso 1 calc R . . H24B H 0.2935 0.2387 0.1066 0.080(8) Uiso 1 calc R . . H24C H 0.2955 0.1394 0.1108 0.079(8) Uiso 1 calc R . . C25 C 0.15574(18) 0.26525(14) 0.18107(15) 0.0628(7) Uani 1 d . . . H25A H 0.0956 0.2480 0.1684 0.097(10) Uiso 1 calc R . . H25B H 0.1783 0.3016 0.1402 0.107(10) Uiso 1 calc R . . H25C H 0.1557 0.2953 0.2303 0.063(7) Uiso 1 calc R . . C26 C 0.05360(12) -0.09335(11) 0.42644(10) 0.0343(4) Uani 1 d . . . C27 C -0.02799(14) -0.05970(12) 0.39728(11) 0.0421(5) Uani 1 d . . . N28 N -0.09412(13) -0.03587(13) 0.37216(12) 0.0632(5) Uani 1 d . . . C29 C 0.04159(13) -0.15669(12) 0.48520(10) 0.0385(4) Uani 1 d . . . N30 N 0.02955(12) -0.20754(12) 0.53159(11) 0.0545(5) Uani 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 0.0323(10) 0.0308(9) 0.0333(8) 0.0028(7) 0.0049(7) 0.0019(7) C2 0.0298(9) 0.0288(8) 0.0368(9) 0.0029(7) 0.0019(7) -0.0004(7) C3 0.0334(10) 0.0309(9) 0.0459(10) 0.0031(8) 0.0034(8) 0.0008(8) C4 0.0302(10) 0.0352(9) 0.0489(10) 0.0074(8) -0.0016(8) 0.0020(8) C5 0.0334(10) 0.0351(9) 0.0376(9) 0.0068(7) -0.0008(8) -0.0052(8) C6 0.0370(11) 0.0321(9) 0.0410(9) -0.0017(8) -0.0009(8) 0.0019(8) C7 0.0310(10) 0.0314(9) 0.0414(9) 0.0036(7) -0.0004(8) 0.0024(8) N8 0.0387(10) 0.0425(9) 0.0462(9) 0.0040(7) -0.0079(7) -0.0048(7) C9 0.0522(14) 0.0497(12) 0.0518(12) -0.0041(10) -0.0085(11) -0.0074(10) C10 0.0377(12) 0.0603(13) 0.0529(12) 0.0091(10) -0.0101(10) -0.0034(10) C11 0.0338(10) 0.0325(9) 0.0402(9) -0.0022(7) 0.0041(8) -0.0007(8) C12 0.0425(12) 0.0290(9) 0.0487(10) -0.0038(8) 0.0082(9) -0.0030(9) N13 0.0579(12) 0.0315(9) 0.0700(12) 0.0021(8) -0.0002(9) 0.0003(8) C14 0.0442(12) 0.0343(10) 0.0452(10) -0.0082(8) 0.0054(9) -0.0021(9) N15 0.0561(12) 0.0526(11) 0.0589(11) -0.0152(9) -0.0012(10) -0.0060(9) C16 0.0311(10) 0.0325(9) 0.0330(8) -0.0050(7) -0.0024(7) -0.0006(7) C17 0.0313(9) 0.0302(8) 0.0328(8) -0.0025(7) -0.0018(7) 0.0000(8) C18 0.0328(10) 0.0353(9) 0.0391(9) 0.0003(7) -0.0014(8) 0.0048(8) C19 0.0335(10) 0.0434(10) 0.0365(9) 0.0014(8) 0.0026(8) 0.0021(9) C20 0.0369(11) 0.0383(9) 0.0353(9) 0.0002(8) -0.0054(8) -0.0036(8) C21 0.0357(11) 0.0332(9) 0.0483(10) 0.0020(8) -0.0022(8) 0.0032(8) C22 0.0320(10) 0.0363(9) 0.0421(10) -0.0015(8) 0.0024(8) 0.0017(8) N23 0.0454(10) 0.0453(9) 0.0488(9) 0.0136(7) -0.0005(8) -0.0003(8) C24 0.0504(13) 0.0546(12) 0.0400(10) 0.0098(9) 0.0006(9) -0.0113(10) C25 0.0650(18) 0.0479(13) 0.0757(16) 0.0208(12) 0.0036(13) 0.0068(12) C26 0.0318(10) 0.0342(9) 0.0367(9) -0.0011(7) -0.0001(7) -0.0008(8) C27 0.0329(11) 0.0433(10) 0.0502(11) 0.0066(9) 0.0023(9) -0.0025(9) N28 0.0363(11) 0.0692(12) 0.0839(14) 0.0250(11) -0.0039(10) 0.0003(10) C29 0.0314(10) 0.0418(10) 0.0424(10) 0.0009(9) 0.0019(8) 0.0000(8) N30 0.0454(11) 0.0583(11) 0.0598(11) 0.0156(9) 0.0073(9) -0.0035(9) _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 C11 1.388(2) . ? C1 C2 1.438(2) . ? C1 C16 1.508(2) . ? C2 C7 1.411(2) . ? C2 C3 1.415(3) . ? C3 C4 1.364(3) . ? C4 C5 1.425(3) . ? C5 N8 1.357(2) . ? C5 C6 1.413(3) . ? C6 C7 1.365(3) . ? N8 C10 1.451(3) . ? N8 C9 1.454(3) . ? C11 C12 1.429(3) . ? C11 C14 1.435(3) . ? C12 N13 1.149(2) . ? C14 N15 1.148(3) . ? C16 C26 1.379(3) . ? C16 C17 1.445(2) . ? C17 C22 1.410(2) . ? C17 C18 1.412(2) . ? C18 C19 1.365(2) . ? C19 C20 1.418(3) . ? C20 N23 1.353(2) . ? C20 C21 1.419(3) . ? C21 C22 1.368(3) . ? N23 C24 1.451(3) . ? N23 C25 1.453(3) . ? C26 C27 1.430(3) . ? C26 C29 1.437(3) . ? C27 N28 1.148(3) . ? C29 N30 1.149(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 C11 C1 C2 125.61(16) . . ? C11 C1 C16 115.96(16) . . ? C2 C1 C16 118.34(14) . . ? C7 C2 C3 116.32(16) . . ? C7 C2 C1 119.58(16) . . ? C3 C2 C1 124.06(16) . . ? C4 C3 C2 121.91(17) . . ? C3 C4 C5 121.25(17) . . ? N8 C5 C6 121.68(17) . . ? N8 C5 C4 121.53(17) . . ? C6 C5 C4 116.79(16) . . ? C7 C6 C5 121.18(17) . . ? C6 C7 C2 122.35(17) . . ? C5 N8 C10 121.43(17) . . ? C5 N8 C9 120.92(17) . . ? C10 N8 C9 117.61(17) . . ? C1 C11 C12 123.49(16) . . ? C1 C11 C14 120.96(17) . . ? C12 C11 C14 115.15(16) . . ? N13 C12 C11 176.6(2) . . ? N15 C14 C11 179.7(2) . . ? C26 C16 C17 124.94(16) . . ? C26 C16 C1 116.45(15) . . ? C17 C16 C1 118.61(15) . . ? C22 C17 C18 116.54(15) . . ? C22 C17 C16 123.39(16) . . ? C18 C17 C16 120.06(15) . . ? C19 C18 C17 122.15(16) . . ? C18 C19 C20 121.09(17) . . ? N23 C20 C19 121.09(17) . . ? N23 C20 C21 121.88(17) . . ? C19 C20 C21 117.02(16) . . ? C22 C21 C20 121.05(17) . . ? C21 C22 C17 122.13(17) . . ? C20 N23 C24 121.39(17) . . ? C20 N23 C25 121.39(18) . . ? C24 N23 C25 117.15(16) . . ? C16 C26 C27 123.61(16) . . ? C16 C26 C29 122.59(17) . . ? C27 C26 C29 113.59(16) . . ? N28 C27 C26 177.0(2) . . ? N30 C29 C26 178.1(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 C11 C1 C2 C7 -161.49(17) . . . . ? C16 C1 C2 C7 14.7(2) . . . . ? C11 C1 C2 C3 16.2(3) . . . . ? C16 C1 C2 C3 -167.62(16) . . . . ? C7 C2 C3 C4 3.6(3) . . . . ? C1 C2 C3 C4 -174.10(16) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 N8 176.84(17) . . . . ? C3 C4 C5 C6 -3.7(3) . . . . ? N8 C5 C6 C7 -176.53(17) . . . . ? C4 C5 C6 C7 4.0(3) . . . . ? C5 C6 C7 C2 -0.5(3) . . . . ? C3 C2 C7 C6 -3.3(3) . . . . ? C1 C2 C7 C6 174.51(16) . . . . ? C6 C5 N8 C10 176.85(17) . . . . ? C4 C5 N8 C10 -3.7(3) . . . . ? C6 C5 N8 C9 -5.6(3) . . . . ? C4 C5 N8 C9 173.86(17) . . . . ? C2 C1 C11 C12 13.7(3) . . . . ? C16 C1 C11 C12 -162.56(16) . . . . ? C2 C1 C11 C14 -173.94(17) . . . . ? C16 C1 C11 C14 9.8(2) . . . . ? C1 C11 C12 N13 80(4) . . . . ? C14 C11 C12 N13 -92(3) . . . . ? C1 C11 C14 N15 -24(56) . . . . ? C12 C11 C14 N15 149(100) . . . . ? C11 C1 C16 C26 62.3(2) . . . . ? C2 C1 C16 C26 -114.27(18) . . . . ? C11 C1 C16 C17 -117.15(17) . . . . ? C2 C1 C16 C17 66.3(2) . . . . ? C26 C16 C17 C22 24.1(3) . . . . ? C1 C16 C17 C22 -156.49(16) . . . . ? C26 C16 C17 C18 -157.27(17) . . . . ? C1 C16 C17 C18 22.1(2) . . . . ? C22 C17 C18 C19 -1.2(2) . . . . ? C16 C17 C18 C19 -179.90(16) . . . . ? C17 C18 C19 C20 1.3(3) . . . . ? C18 C19 C20 N23 178.39(17) . . . . ? C18 C19 C20 C21 -0.9(3) . . . . ? N23 C20 C21 C22 -178.81(17) . . . . ? C19 C20 C21 C22 0.5(3) . . . . ? C20 C21 C22 C17 -0.4(3) . . . . ? C18 C17 C22 C21 0.8(3) . . . . ? C16 C17 C22 C21 179.42(17) . . . . ? C19 C20 N23 C24 -2.3(3) . . . . ? C21 C20 N23 C24 176.97(17) . . . . ? C19 C20 N23 C25 -179.0(2) . . . . ? C21 C20 N23 C25 0.2(3) . . . . ? C17 C16 C26 C27 11.5(3) . . . . ? C1 C16 C26 C27 -167.95(16) . . . . ? C17 C16 C26 C29 -174.09(16) . . . . ? C1 C16 C26 C29 6.5(2) . . . . ? C16 C26 C27 N28 102(4) . . . . ? C29 C26 C27 N28 -73(4) . . . . ? C16 C26 C29 N30 -159(6) . . . . ? C27 C26 C29 N30 16(6) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.138 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.033 data_michi7_D_04 _database_code_depnum_ccdc_archive 'CCDC 256340' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 N3' _chemical_formula_sum 'C14 H11 N3' _chemical_formula_weight 221.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.0006(3) _cell_length_b 17.9661(10) _cell_length_c 17.145(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.308(3) _cell_angle_gamma 90.00 _cell_volume 1224.85(18) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1445 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 21.98 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 2749 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 21.98 _reflns_number_total 1465 _reflns_number_gt 1176 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo + Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et Al., 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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^)+(0.0716P)^2^+0.0629P] 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 'H-atoms riding' _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.079(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1465 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1280 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7788(5) 0.66727(11) 0.99859(13) 0.0516(6) Uani 1 d . . . C2 C 0.7316(6) 0.59289(12) 0.97521(14) 0.0605(6) Uani 1 d . . . H2A H 0.6463 0.5592 1.0091 0.066(6) Uiso 1 calc R . . C3 C 0.8079(6) 0.56892(12) 0.90393(14) 0.0603(6) Uani 1 d . . . H3A H 0.7746 0.5191 0.8904 0.072(7) Uiso 1 calc R . . C4 C 0.9340(5) 0.61699(11) 0.85097(13) 0.0548(6) Uani 1 d . . . C5 C 0.9806(6) 0.69111(12) 0.87326(14) 0.0612(6) Uani 1 d . . . H5A H 1.0658 0.7244 0.8389 0.065(6) Uiso 1 calc R . . C6 C 0.9037(6) 0.71591(11) 0.94447(14) 0.0591(6) Uani 1 d . . . H6A H 0.9346 0.7659 0.9574 0.079(7) Uiso 1 calc R . . N7 N 0.7056(4) 0.69108(9) 1.07012(11) 0.0603(6) Uani 1 d . . . C8 C 0.5663(6) 0.63997(14) 1.12357(15) 0.0699(7) Uani 1 d . . . H8A H 0.5322 0.6656 1.1712 0.104(9) Uiso 1 calc R . . H8B H 0.7195 0.5994 1.1354 0.087(8) Uiso 1 calc R . . H8C H 0.3552 0.6211 1.0996 0.112(10) Uiso 1 calc R . . C9 C 0.7678(8) 0.76647(14) 1.09624(17) 0.0781(8) Uani 1 d . . . H9A H 0.9975 0.7793 1.0913 0.122(11) Uiso 1 calc R . . H9B H 0.7265 0.7708 1.1502 0.118(11) Uiso 1 calc R . . H9C H 0.6210 0.7996 1.0647 0.140(13) Uiso 1 calc R . . C10 C 1.0210(6) 0.58942(12) 0.77858(15) 0.0624(7) Uani 1 d . . . C11 C 1.0962(6) 0.56195(12) 0.71834(15) 0.0636(7) Uani 1 d . . . C12 C 1.1930(5) 0.53108(13) 0.65016(13) 0.0597(6) Uani 1 d . . . H12A H 1.2981 0.5622 0.6170 0.070(7) Uiso 1 calc R . . C13 C 1.1460(5) 0.45913(12) 0.62829(13) 0.0535(6) Uani 1 d . . . C14 C 1.2543(6) 0.43187(11) 0.55742(14) 0.0567(6) Uani 1 d . . . N15 N 1.3445(6) 0.40994(11) 0.50076(14) 0.0741(6) Uani 1 d . . . C16 C 0.9849(6) 0.40650(13) 0.67407(14) 0.0610(6) Uani 1 d . . . N17 N 0.8525(6) 0.36423(14) 0.70989(14) 0.0893(8) Uani 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 0.0512(12) 0.0502(12) 0.0537(14) 0.0011(10) 0.0074(10) 0.0004(9) C2 0.0705(14) 0.0498(13) 0.0629(16) 0.0022(11) 0.0152(12) -0.0088(10) C3 0.0702(14) 0.0467(12) 0.0645(16) -0.0071(11) 0.0098(12) -0.0049(10) C4 0.0587(12) 0.0546(13) 0.0520(14) -0.0050(10) 0.0100(11) 0.0024(10) C5 0.0748(15) 0.0536(13) 0.0580(15) 0.0021(11) 0.0202(12) -0.0049(11) C6 0.0742(15) 0.0450(12) 0.0606(16) -0.0032(11) 0.0178(12) -0.0035(10) N7 0.0702(12) 0.0579(11) 0.0551(12) -0.0034(9) 0.0177(10) -0.0052(9) C8 0.0746(16) 0.0795(16) 0.0577(16) 0.0082(13) 0.0175(13) 0.0006(13) C9 0.098(2) 0.0693(16) 0.0715(19) -0.0189(13) 0.0279(16) -0.0057(14) C10 0.0669(15) 0.0608(14) 0.0598(17) -0.0052(12) 0.0087(12) 0.0031(11) C11 0.0701(15) 0.0645(14) 0.0570(16) -0.0052(13) 0.0109(12) 0.0058(11) C12 0.0643(14) 0.0637(14) 0.0523(15) 0.0018(11) 0.0120(12) 0.0073(11) C13 0.0566(12) 0.0592(14) 0.0449(13) 0.0032(10) 0.0069(10) 0.0075(10) C14 0.0655(14) 0.0551(13) 0.0502(15) 0.0005(11) 0.0091(12) 0.0073(10) N15 0.0966(15) 0.0662(13) 0.0625(14) -0.0035(11) 0.0218(12) 0.0086(11) C16 0.0643(14) 0.0706(15) 0.0486(15) -0.0018(12) 0.0080(12) 0.0033(12) N17 0.0997(17) 0.0973(17) 0.0737(16) 0.0074(13) 0.0227(13) -0.0172(13) _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 N7 1.361(3) . ? C1 C2 1.402(3) . ? C1 C6 1.406(3) . ? C2 C3 1.362(3) . ? C3 C4 1.388(3) . ? C4 C5 1.392(3) . ? C4 C10 1.415(3) . ? C5 C6 1.366(3) . ? N7 C9 1.440(3) . ? N7 C8 1.451(3) . ? C10 C11 1.212(3) . ? C11 C12 1.387(3) . ? C12 C13 1.353(3) . ? C13 C14 1.421(3) . ? C13 C16 1.427(3) . ? C14 N15 1.143(3) . ? C16 N17 1.143(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 N7 C1 C2 121.46(19) . . ? N7 C1 C6 121.78(19) . . ? C2 C1 C6 116.8(2) . . ? C3 C2 C1 121.4(2) . . ? C2 C3 C4 121.6(2) . . ? C3 C4 C5 117.6(2) . . ? C3 C4 C10 119.88(19) . . ? C5 C4 C10 122.5(2) . . ? C6 C5 C4 121.4(2) . . ? C5 C6 C1 121.2(2) . . ? C1 N7 C9 121.95(19) . . ? C1 N7 C8 120.38(19) . . ? C9 N7 C8 117.65(19) . . ? C11 C10 C4 176.4(2) . . ? C10 C11 C12 178.2(3) . . ? C13 C12 C11 124.9(2) . . ? C12 C13 C14 121.3(2) . . ? C12 C13 C16 122.5(2) . . ? C14 C13 C16 116.13(19) . . ? N15 C14 C13 179.3(2) . . ? N17 C16 C13 179.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N7 C1 C2 C3 -179.4(2) . . . . ? C6 C1 C2 C3 0.9(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C2 C3 C4 C10 177.8(2) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C10 C4 C5 C6 -178.1(2) . . . . ? C4 C5 C6 C1 0.9(3) . . . . ? N7 C1 C6 C5 179.10(19) . . . . ? C2 C1 C6 C5 -1.2(3) . . . . ? C2 C1 N7 C9 177.0(2) . . . . ? C6 C1 N7 C9 -3.3(3) . . . . ? C2 C1 N7 C8 -1.8(3) . . . . ? C6 C1 N7 C8 177.9(2) . . . . ? C3 C4 C10 C11 -19(4) . . . . ? C5 C4 C10 C11 158(4) . . . . ? C4 C10 C11 C12 -96(8) . . . . ? C10 C11 C12 C13 120(8) . . . . ? C11 C12 C13 C14 -179.7(2) . . . . ? C11 C12 C13 C16 0.6(3) . . . . ? C12 C13 C14 N15 76(19) . . . . ? C16 C13 C14 N15 -105(19) . . . . ? C12 C13 C16 N17 118(16) . . . . ? C14 C13 C16 N17 -61(16) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 21.98 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.129 _refine_diff_density_min -0.096 _refine_diff_density_rms 0.028