# Electronic Supplementary Material (ESI) for Polymer Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 1478 loop_ _publ_author_name 'Michinobu, Tsuyoshi' 'Seo, Chayeon' 'Noguchi, Keiichi' 'Mori, Takehiko' _publ_contact_author_name 'Michinobu, Tsuyoshi' _publ_contact_author_email michinobu.t.aa@m.titech.ac.jp _publ_section_title ; Effects of click postfunctionalization on thermal stability and field effect transistor performances of aromatic polyamines ; # Attachment '- 4a.cif' data_I _database_code_depnum_ccdc_archive 'CCDC 867035' #TrackingRef '- 4a.cif' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C22 H16 N6), 0.5(C2 H4 Cl2)' _chemical_formula_sum 'C45 H34 Cl N12' _chemical_formula_weight 778.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z _cell_length_a 11.8246(2) _cell_length_b 13.8037(3) _cell_length_c 14.9944(3) _cell_angle_alpha 114.8040(10) _cell_angle_beta 105.6390(10) _cell_angle_gamma 98.9430(10) _cell_volume 2035.95(8) _cell_formula_units_Z 2 _cell_measurement_temperature 193 _cell_measurement_reflns_used 24483 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 68.2 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 810 _exptl_absorpt_coefficient_mu 1.217 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.562 _exptl_absorpt_correction_T_max 0.885 _exptl_special_details ; ? ; _diffrn_ambient_temperature 193 _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'roating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 28971 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _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 3.50 _diffrn_reflns_theta_max 68.23 _reflns_number_total 7247 _reflns_number_gt 6191 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0741P)^2^+0.4383P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7247 _refine_ls_number_parameters 527 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.30194(5) 0.43340(5) 0.43226(4) 0.06772(18) Uani 1 1 d . . . N1 N 0.34456(19) 0.48921(17) -0.10240(16) 0.0711(5) Uani 1 1 d . . . N2 N 0.42384(17) 0.19614(16) -0.10008(12) 0.0619(5) Uani 1 1 d . . . N3 N 0.14896(15) 0.00621(12) 0.04859(13) 0.0531(4) Uani 1 1 d . . . N4 N 0.00145(14) 0.18741(13) -0.11088(12) 0.0500(4) Uani 1 1 d . . . N5 N 0.0534(2) 0.67650(18) 0.24150(16) 0.0837(7) Uani 1 1 d . . . H5A H 0.0356 0.6801 0.2959 0.100 Uiso 1 1 calc R . . H5B H 0.0329 0.7203 0.2152 0.100 Uiso 1 1 calc R . . N6 N 0.73837(14) 0.32502(12) 0.37821(13) 0.0495(4) Uani 1 1 d . . . N7 N 0.05122(15) 0.31302(13) 0.58012(12) 0.0503(4) Uani 1 1 d . . . N8 N 0.43862(16) 0.37096(14) 0.66857(15) 0.0676(5) Uani 1 1 d . . . N9 N 0.19048(14) -0.06151(13) 0.51383(12) 0.0482(4) Uani 1 1 d . . . N10 N -0.16818(15) -0.18554(13) 0.27885(13) 0.0520(4) Uani 1 1 d . . . N11 N 0.55587(15) -0.04613(15) 0.30427(13) 0.0579(4) Uani 1 1 d . . . H11A H 0.5362 -0.0951 0.2373 0.069 Uiso 1 1 calc R . . H11B H 0.6308 -0.0264 0.3504 0.069 Uiso 1 1 calc R . . N12 N -0.22466(16) 0.20232(14) 0.10916(13) 0.0548(4) Uani 1 1 d . . . C1 C 0.28479(15) 0.36474(12) 0.05173(12) 0.0336(3) Uani 1 1 d . . . C2 C 0.28827(15) 0.27465(12) 0.08405(12) 0.0324(3) Uani 1 1 d . . . C3 C 0.33092(15) 0.35525(13) -0.02516(12) 0.0358(3) Uani 1 1 d . . . C4 C 0.33760(17) 0.43029(16) -0.06755(14) 0.0457(4) Uani 1 1 d . . . C5 C 0.38167(17) 0.26632(15) -0.06753(13) 0.0426(4) Uani 1 1 d . . . C6 C 0.18173(15) 0.18530(13) 0.03012(12) 0.0349(3) Uani 1 1 d . . . C7 C 0.16397(15) 0.08621(13) 0.04132(13) 0.0392(4) Uani 1 1 d . . . C8 C 0.08001(16) 0.18490(13) -0.04825(13) 0.0387(4) Uani 1 1 d . . . C9 C 0.22967(17) 0.44804(14) 0.10144(13) 0.0407(4) Uani 1 1 d . . . C10 C 0.20314(17) 0.45771(14) 0.18948(13) 0.0420(4) Uani 1 1 d . . . H10 H 0.2252 0.4103 0.2178 0.050 Uiso 1 1 calc R . . C11 C 0.14664(19) 0.53274(15) 0.23675(14) 0.0492(4) Uani 1 1 d . . . H11 H 0.1308 0.5362 0.2967 0.059 Uiso 1 1 calc R . . C12 C 0.1122(2) 0.60378(18) 0.19845(17) 0.0601(6) Uani 1 1 d . . . C13 C 0.1366(3) 0.5939(3) 0.1096(2) 0.1108(13) Uani 1 1 d . . . H13 H 0.1138 0.6409 0.0810 0.133 Uiso 1 1 calc R . . C14 C 0.1923(3) 0.5186(2) 0.0627(2) 0.0961(11) Uani 1 1 d . . . H14 H 0.2061 0.5139 0.0017 0.115 Uiso 1 1 calc R . . C15 C 0.40043(15) 0.28936(12) 0.16366(12) 0.0336(3) Uani 1 1 d . . . C16 C 0.51093(15) 0.36990(13) 0.19130(12) 0.0358(3) Uani 1 1 d . . . H16 H 0.5085 0.4177 0.1605 0.043 Uiso 1 1 calc R . . C17 C 0.62105(16) 0.38209(13) 0.26032(13) 0.0388(4) Uani 1 1 d . . . H17 H 0.6934 0.4362 0.2748 0.047 Uiso 1 1 calc R . . C18 C 0.62931(16) 0.31561(13) 0.31071(13) 0.0406(4) Uani 1 1 d . . . C19 C 0.51796(17) 0.23905(15) 0.28844(15) 0.0467(4) Uani 1 1 d . . . H19 H 0.5193 0.1957 0.3237 0.056 Uiso 1 1 calc R . . C20 C 0.40839(16) 0.22590(14) 0.21728(14) 0.0433(4) Uani 1 1 d . . . H20 H 0.3357 0.1727 0.2035 0.052 Uiso 1 1 calc R . . C21 C 0.85192(17) 0.40627(17) 0.40444(17) 0.0559(5) Uani 1 1 d . . . H21A H 0.9217 0.3943 0.4469 0.067 Uiso 1 1 calc R . . H21B H 0.8485 0.4821 0.4450 0.067 Uiso 1 1 calc R . . H21C H 0.8626 0.3975 0.3391 0.067 Uiso 1 1 calc R . . C22 C 0.74329(19) 0.26131(18) 0.43515(17) 0.0595(5) Uani 1 1 d . . . H22A H 0.8296 0.2737 0.4752 0.071 Uiso 1 1 calc R . . H22B H 0.7034 0.1813 0.3845 0.071 Uiso 1 1 calc R . . H22C H 0.7002 0.2861 0.4841 0.071 Uiso 1 1 calc R . . C23 C 0.20341(14) 0.14032(12) 0.43960(12) 0.0332(3) Uani 1 1 d . . . C24 C 0.07093(14) 0.06944(13) 0.37247(12) 0.0332(3) Uani 1 1 d . . . C25 C 0.22405(15) 0.23788(13) 0.52938(12) 0.0359(3) Uani 1 1 d . . . C26 C 0.12519(16) 0.27616(13) 0.55528(13) 0.0385(4) Uani 1 1 d . . . C27 C 0.34369(17) 0.31156(14) 0.60577(14) 0.0448(4) Uani 1 1 d . . . C28 C 0.03730(14) -0.02485(13) 0.38205(12) 0.0339(3) Uani 1 1 d . . . C29 C 0.12396(15) -0.04483(13) 0.45519(12) 0.0363(3) Uani 1 1 d . . . C30 C -0.07840(16) -0.11207(14) 0.32300(13) 0.0381(4) Uani 1 1 d . . . C31 C 0.29719(14) 0.09568(12) 0.40718(12) 0.0330(3) Uani 1 1 d . . . C32 C 0.41839(15) 0.12417(13) 0.47697(12) 0.0361(3) Uani 1 1 d . . . H32 H 0.4424 0.1775 0.5495 0.043 Uiso 1 1 calc R . . C33 C 0.50271(15) 0.07711(13) 0.44318(12) 0.0372(4) Uani 1 1 d . . . H33 H 0.5837 0.0977 0.4925 0.045 Uiso 1 1 calc R . . C34 C 0.47096(16) -0.00133(14) 0.33632(13) 0.0399(4) Uani 1 1 d . . . C35 C 0.35028(16) -0.03042(15) 0.26552(13) 0.0432(4) Uani 1 1 d . . . H35 H 0.3269 -0.0827 0.1928 0.052 Uiso 1 1 calc R . . C36 C 0.26602(15) 0.01582(13) 0.30034(13) 0.0389(4) Uani 1 1 d . . . H36 H 0.1844 -0.0064 0.2513 0.047 Uiso 1 1 calc R . . C37 C -0.00637(15) 0.10283(13) 0.30596(12) 0.0351(3) Uani 1 1 d . . . C38 C -0.13619(16) 0.05665(15) 0.25894(14) 0.0437(4) Uani 1 1 d . . . H38 H -0.1755 0.0017 0.2724 0.052 Uiso 1 1 calc R . . C39 C -0.20673(17) 0.08896(16) 0.19453(15) 0.0484(4) Uani 1 1 d . . . H39 H -0.2938 0.0557 0.1641 0.058 Uiso 1 1 calc R . . C40 C -0.15284(17) 0.17069(15) 0.17240(13) 0.0448(4) Uani 1 1 d . . . C41 C -0.02330(17) 0.21765(15) 0.21944(14) 0.0449(4) Uani 1 1 d . . . H41 H 0.0161 0.2730 0.2064 0.054 Uiso 1 1 calc R . . C42 C 0.04638(16) 0.18440(14) 0.28375(13) 0.0399(4) Uani 1 1 d . . . H42 H 0.1334 0.2177 0.3144 0.048 Uiso 1 1 calc R . . C43 C -0.3550(2) 0.1410(2) 0.04934(17) 0.0682(6) Uani 1 1 d . . . H43A H -0.3918 0.1759 0.0088 0.082 Uiso 1 1 calc R . . H43B H -0.3964 0.1425 0.0982 0.082 Uiso 1 1 calc R . . H43C H -0.3646 0.0631 0.0006 0.082 Uiso 1 1 calc R . . C44 C -0.1699(2) 0.2837(2) 0.0829(2) 0.0759(7) Uani 1 1 d . . . H44A H -0.2352 0.3038 0.0448 0.091 Uiso 1 1 calc R . . H44B H -0.1245 0.2510 0.0380 0.091 Uiso 1 1 calc R . . H44C H -0.1131 0.3510 0.1481 0.091 Uiso 1 1 calc R . . C45 C 0.4560(2) 0.5060(2) 0.45974(18) 0.0717(6) Uani 1 1 d . . . H45A H 0.4735 0.4758 0.3940 0.086 Uiso 1 1 calc R . . H45B H 0.4649 0.5865 0.4844 0.086 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 Cl1 0.0568(3) 0.0812(4) 0.0574(3) 0.0345(3) 0.0187(2) 0.0034(3) N1 0.0857(14) 0.0884(13) 0.0948(14) 0.0729(12) 0.0570(12) 0.0433(12) N2 0.0718(12) 0.0803(12) 0.0418(8) 0.0269(8) 0.0228(8) 0.0498(10) N3 0.0546(10) 0.0429(8) 0.0557(9) 0.0296(7) 0.0071(8) 0.0066(7) N4 0.0441(9) 0.0516(9) 0.0532(9) 0.0320(7) 0.0070(7) 0.0126(7) N5 0.140(2) 0.0965(15) 0.0880(14) 0.0662(12) 0.0813(15) 0.0911(15) N6 0.0358(8) 0.0465(8) 0.0619(9) 0.0330(7) 0.0035(7) 0.0085(7) N7 0.0484(9) 0.0579(9) 0.0522(9) 0.0278(8) 0.0215(8) 0.0273(8) N8 0.0472(11) 0.0459(9) 0.0710(11) 0.0044(8) 0.0063(9) 0.0140(8) N9 0.0415(9) 0.0559(9) 0.0560(9) 0.0371(8) 0.0131(7) 0.0177(7) N10 0.0433(9) 0.0501(9) 0.0553(9) 0.0316(8) 0.0041(7) 0.0037(8) N11 0.0429(9) 0.0708(11) 0.0457(8) 0.0126(8) 0.0174(7) 0.0255(8) N12 0.0551(10) 0.0722(11) 0.0540(9) 0.0424(9) 0.0168(8) 0.0347(9) C1 0.0345(9) 0.0346(8) 0.0353(8) 0.0206(7) 0.0116(7) 0.0118(7) C2 0.0368(9) 0.0343(8) 0.0341(7) 0.0200(6) 0.0163(7) 0.0157(7) C3 0.0377(9) 0.0392(8) 0.0359(8) 0.0216(7) 0.0140(7) 0.0154(7) C4 0.0482(11) 0.0570(10) 0.0523(10) 0.0362(9) 0.0279(9) 0.0231(9) C5 0.0446(10) 0.0559(10) 0.0340(8) 0.0243(8) 0.0154(7) 0.0236(9) C6 0.0356(9) 0.0373(8) 0.0372(8) 0.0219(7) 0.0132(7) 0.0145(7) C7 0.0366(9) 0.0373(8) 0.0405(8) 0.0205(7) 0.0086(7) 0.0088(7) C8 0.0376(9) 0.0377(8) 0.0429(9) 0.0229(7) 0.0131(8) 0.0104(7) C9 0.0516(11) 0.0428(9) 0.0452(9) 0.0285(8) 0.0258(8) 0.0240(8) C10 0.0545(11) 0.0419(9) 0.0427(9) 0.0267(7) 0.0226(8) 0.0219(8) C11 0.0674(13) 0.0532(10) 0.0460(10) 0.0292(8) 0.0331(9) 0.0310(10) C12 0.0892(16) 0.0653(12) 0.0641(12) 0.0427(11) 0.0488(12) 0.0519(12) C13 0.210(4) 0.137(2) 0.131(2) 0.117(2) 0.136(3) 0.144(3) C14 0.182(3) 0.118(2) 0.113(2) 0.1000(19) 0.119(2) 0.121(2) C15 0.0337(9) 0.0331(7) 0.0363(8) 0.0191(6) 0.0120(7) 0.0113(7) C16 0.0410(9) 0.0333(8) 0.0375(8) 0.0207(7) 0.0147(7) 0.0120(7) C17 0.0353(9) 0.0348(8) 0.0453(9) 0.0210(7) 0.0127(7) 0.0075(7) C18 0.0355(9) 0.0378(8) 0.0452(9) 0.0220(7) 0.0079(7) 0.0104(7) C19 0.0424(10) 0.0456(9) 0.0554(10) 0.0360(9) 0.0071(8) 0.0078(8) C20 0.0353(9) 0.0445(9) 0.0506(10) 0.0315(8) 0.0069(8) 0.0049(7) C21 0.0351(10) 0.0534(11) 0.0689(13) 0.0315(10) 0.0054(9) 0.0073(8) C22 0.0463(11) 0.0606(12) 0.0682(12) 0.0424(11) 0.0003(10) 0.0127(9) C23 0.0336(9) 0.0351(8) 0.0354(8) 0.0222(7) 0.0101(6) 0.0118(7) C24 0.0306(8) 0.0371(8) 0.0337(7) 0.0181(6) 0.0118(6) 0.0129(7) C25 0.0333(9) 0.0369(8) 0.0399(8) 0.0206(7) 0.0124(7) 0.0135(7) C26 0.0392(10) 0.0391(8) 0.0384(8) 0.0210(7) 0.0114(7) 0.0135(7) C27 0.0400(10) 0.0366(8) 0.0484(10) 0.0134(8) 0.0130(8) 0.0152(8) C28 0.0304(8) 0.0379(8) 0.0358(8) 0.0207(7) 0.0103(6) 0.0119(7) C29 0.0336(9) 0.0370(8) 0.0403(8) 0.0213(7) 0.0126(7) 0.0103(7) C30 0.0372(10) 0.0408(9) 0.0395(8) 0.0240(7) 0.0105(7) 0.0135(8) C31 0.0316(8) 0.0336(7) 0.0360(8) 0.0193(6) 0.0116(6) 0.0099(6) C32 0.0363(9) 0.0383(8) 0.0335(8) 0.0178(7) 0.0111(7) 0.0131(7) C33 0.0309(9) 0.0417(8) 0.0376(8) 0.0198(7) 0.0094(7) 0.0119(7) C34 0.0377(9) 0.0432(9) 0.0415(9) 0.0207(7) 0.0174(7) 0.0144(7) C35 0.0408(10) 0.0460(9) 0.0348(8) 0.0131(7) 0.0136(7) 0.0123(8) C36 0.0319(9) 0.0418(9) 0.0363(8) 0.0171(7) 0.0079(7) 0.0082(7) C37 0.0330(9) 0.0374(8) 0.0375(8) 0.0215(7) 0.0105(7) 0.0126(7) C38 0.0354(10) 0.0472(9) 0.0540(10) 0.0316(8) 0.0126(8) 0.0136(8) C39 0.0341(10) 0.0553(10) 0.0555(10) 0.0314(9) 0.0076(8) 0.0159(8) C40 0.0499(11) 0.0512(10) 0.0418(9) 0.0271(8) 0.0154(8) 0.0267(9) C41 0.0475(11) 0.0480(9) 0.0502(10) 0.0328(8) 0.0174(8) 0.0175(8) C42 0.0373(9) 0.0429(9) 0.0428(9) 0.0245(7) 0.0127(7) 0.0139(7) C43 0.0611(14) 0.0925(16) 0.0564(12) 0.0414(12) 0.0104(10) 0.0423(13) C44 0.0877(18) 0.1009(18) 0.0857(16) 0.0750(16) 0.0364(14) 0.0527(15) C45 0.0690(16) 0.0841(16) 0.0578(13) 0.0339(12) 0.0263(12) 0.0091(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 Cl1 C45 1.781(2) . ? N1 C4 1.140(2) . ? N2 C5 1.145(2) . ? N3 C7 1.146(2) . ? N4 C8 1.146(2) . ? N5 C12 1.350(2) . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? N6 C18 1.356(2) . ? N6 C21 1.447(2) . ? N6 C22 1.458(2) . ? N7 C26 1.148(2) . ? N8 C27 1.147(2) . ? N9 C29 1.139(2) . ? N10 C30 1.147(2) . ? N11 C34 1.351(2) . ? N11 H11A 0.8800 . ? N11 H11B 0.8800 . ? N12 C40 1.356(2) . ? N12 C43 1.452(3) . ? N12 C44 1.456(3) . ? C1 C3 1.371(2) . ? C1 C9 1.442(2) . ? C1 C2 1.5145(19) . ? C2 C6 1.376(2) . ? C2 C15 1.444(2) . ? C3 C4 1.427(2) . ? C3 C5 1.432(2) . ? C6 C8 1.435(2) . ? C6 C7 1.437(2) . ? C9 C10 1.395(2) . ? C9 C14 1.397(2) . ? C10 C11 1.370(2) . ? C10 H10 0.9500 . ? C11 C12 1.388(2) . ? C11 H11 0.9500 . ? C12 C13 1.394(3) . ? C13 C14 1.364(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.409(2) . ? C15 C20 1.414(2) . ? C16 C17 1.362(2) . ? C16 H16 0.9500 . ? C17 C18 1.411(2) . ? C17 H17 0.9500 . ? C18 C19 1.413(2) . ? C19 C20 1.367(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C25 1.373(2) . ? C23 C31 1.448(2) . ? C23 C24 1.507(2) . ? C24 C28 1.378(2) . ? C24 C37 1.438(2) . ? C25 C27 1.432(2) . ? C25 C26 1.436(2) . ? C28 C30 1.430(2) . ? C28 C29 1.437(2) . ? C31 C32 1.405(2) . ? C31 C36 1.411(2) . ? C32 C33 1.368(2) . ? C32 H32 0.9500 . ? C33 C34 1.405(2) . ? C33 H33 0.9500 . ? C34 C35 1.404(2) . ? C35 C36 1.368(2) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 C42 1.406(2) . ? C37 C38 1.412(2) . ? C38 C39 1.367(2) . ? C38 H38 0.9500 . ? C39 C40 1.412(3) . ? C39 H39 0.9500 . ? C40 C41 1.410(3) . ? C41 C42 1.371(2) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 C45 1.454(5) 2_666 ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? 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 C12 N5 H5A 120.0 . . ? C12 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C18 N6 C21 121.43(15) . . ? C18 N6 C22 120.88(15) . . ? C21 N6 C22 117.41(15) . . ? C34 N11 H11A 120.0 . . ? C34 N11 H11B 120.0 . . ? H11A N11 H11B 120.0 . . ? C40 N12 C43 120.88(17) . . ? C40 N12 C44 120.85(18) . . ? C43 N12 C44 117.19(16) . . ? C3 C1 C9 127.08(13) . . ? C3 C1 C2 115.71(13) . . ? C9 C1 C2 117.17(13) . . ? C6 C2 C15 127.58(13) . . ? C6 C2 C1 114.28(13) . . ? C15 C2 C1 118.12(13) . . ? C1 C3 C4 125.57(14) . . ? C1 C3 C5 120.23(14) . . ? C4 C3 C5 114.17(14) . . ? N1 C4 C3 178.5(2) . . ? N2 C5 C3 179.0(2) . . ? C2 C6 C8 119.42(13) . . ? C2 C6 C7 125.27(14) . . ? C8 C6 C7 115.24(14) . . ? N3 C7 C6 178.95(19) . . ? N4 C8 C6 177.67(18) . . ? C10 C9 C14 115.55(15) . . ? C10 C9 C1 120.72(14) . . ? C14 C9 C1 123.61(15) . . ? C11 C10 C9 122.69(15) . . ? C11 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? C10 C11 C12 121.04(16) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? N5 C12 C11 122.46(18) . . ? N5 C12 C13 120.62(18) . . ? C11 C12 C13 116.88(17) . . ? C14 C13 C12 121.71(19) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C9 122.11(18) . . ? C13 C14 H14 118.9 . . ? C9 C14 H14 118.9 . . ? C16 C15 C20 115.98(14) . . ? C16 C15 C2 120.17(13) . . ? C20 C15 C2 123.85(15) . . ? C17 C16 C15 122.69(14) . . ? C17 C16 H16 118.7 . . ? C15 C16 H16 118.7 . . ? C16 C17 C18 121.02(15) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? N6 C18 C17 121.95(16) . . ? N6 C18 C19 121.20(15) . . ? C17 C18 C19 116.85(15) . . ? C20 C19 C18 121.53(15) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C19 C20 C15 121.77(16) . . ? C19 C20 H20 119.1 . . ? C15 C20 H20 119.1 . . ? N6 C21 H21A 109.5 . . ? N6 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N6 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N6 C22 H22A 109.5 . . ? N6 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N6 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C25 C23 C31 126.05(15) . . ? C25 C23 C24 116.83(14) . . ? C31 C23 C24 116.99(13) . . ? C28 C24 C37 126.54(15) . . ? C28 C24 C23 113.75(13) . . ? C37 C24 C23 119.71(13) . . ? C23 C25 C27 124.46(15) . . ? C23 C25 C26 122.34(15) . . ? C27 C25 C26 113.20(14) . . ? N7 C26 C25 175.88(19) . . ? N8 C27 C25 178.6(2) . . ? C24 C28 C30 126.77(14) . . ? C24 C28 C29 120.08(14) . . ? C30 C28 C29 113.12(13) . . ? N9 C29 C28 178.38(18) . . ? N10 C30 C28 175.68(16) . . ? C32 C31 C36 116.96(14) . . ? C32 C31 C23 123.85(14) . . ? C36 C31 C23 119.16(14) . . ? C33 C32 C31 121.72(14) . . ? C33 C32 H32 119.1 . . ? C31 C32 H32 119.1 . . ? C32 C33 C34 120.78(15) . . ? C32 C33 H33 119.6 . . ? C34 C33 H33 119.6 . . ? N11 C34 C35 121.91(15) . . ? N11 C34 C33 119.91(15) . . ? C35 C34 C33 118.18(14) . . ? C36 C35 C34 120.63(15) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C31 121.72(15) . . ? C35 C36 H36 119.1 . . ? C31 C36 H36 119.1 . . ? C42 C37 C38 116.48(14) . . ? C42 C37 C24 120.21(15) . . ? C38 C37 C24 123.30(14) . . ? C39 C38 C37 121.75(16) . . ? C39 C38 H38 119.1 . . ? C37 C38 H38 119.1 . . ? C38 C39 C40 121.36(17) . . ? C38 C39 H39 119.3 . . ? C40 C39 H39 119.3 . . ? N12 C40 C41 122.34(17) . . ? N12 C40 C39 120.37(17) . . ? C41 C40 C39 117.28(15) . . ? C42 C41 C40 120.78(16) . . ? C42 C41 H41 119.6 . . ? C40 C41 H41 119.6 . . ? C41 C42 C37 122.35(16) . . ? C41 C42 H42 118.8 . . ? C37 C42 H42 118.8 . . ? N12 C43 H43A 109.5 . . ? N12 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? N12 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? N12 C44 H44A 109.5 . . ? N12 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? N12 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C45 C45 Cl1 110.9(2) 2_666 . ? C45 C45 H45A 109.5 2_666 . ? Cl1 C45 H45A 109.5 . . ? C45 C45 H45B 109.5 2_666 . ? Cl1 C45 H45B 109.5 . . ? H45A C45 H45B 108.0 . . ? 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 C3 C1 C2 C6 -93.39(18) . . . . ? C9 C1 C2 C6 84.31(18) . . . . ? C3 C1 C2 C15 85.06(18) . . . . ? C9 C1 C2 C15 -97.24(18) . . . . ? C9 C1 C3 C4 2.9(3) . . . . ? C2 C1 C3 C4 -179.70(16) . . . . ? C9 C1 C3 C5 -179.25(17) . . . . ? C2 C1 C3 C5 -1.8(2) . . . . ? C15 C2 C6 C8 -178.77(15) . . . . ? C1 C2 C6 C8 -0.5(2) . . . . ? C15 C2 C6 C7 -2.2(3) . . . . ? C1 C2 C6 C7 176.12(15) . . . . ? C3 C1 C9 C10 -170.48(17) . . . . ? C2 C1 C9 C10 12.1(2) . . . . ? C3 C1 C9 C14 13.7(3) . . . . ? C2 C1 C9 C14 -163.7(2) . . . . ? C14 C9 C10 C11 -1.3(3) . . . . ? C1 C9 C10 C11 -177.50(18) . . . . ? C9 C10 C11 C12 0.2(3) . . . . ? C10 C11 C12 N5 178.2(2) . . . . ? C10 C11 C12 C13 0.7(4) . . . . ? N5 C12 C13 C14 -177.9(3) . . . . ? C11 C12 C13 C14 -0.4(5) . . . . ? C12 C13 C14 C9 -0.9(6) . . . . ? C10 C9 C14 C13 1.7(5) . . . . ? C1 C9 C14 C13 177.7(3) . . . . ? C6 C2 C15 C16 163.42(15) . . . . ? C1 C2 C15 C16 -14.8(2) . . . . ? C6 C2 C15 C20 -15.9(3) . . . . ? C1 C2 C15 C20 165.88(15) . . . . ? C20 C15 C16 C17 4.0(2) . . . . ? C2 C15 C16 C17 -175.33(15) . . . . ? C15 C16 C17 C18 -1.9(3) . . . . ? C21 N6 C18 C17 1.8(3) . . . . ? C22 N6 C18 C17 175.50(18) . . . . ? C21 N6 C18 C19 -177.59(18) . . . . ? C22 N6 C18 C19 -3.8(3) . . . . ? C16 C17 C18 N6 178.79(16) . . . . ? C16 C17 C18 C19 -1.8(2) . . . . ? N6 C18 C19 C20 -177.36(18) . . . . ? C17 C18 C19 C20 3.3(3) . . . . ? C18 C19 C20 C15 -1.0(3) . . . . ? C16 C15 C20 C19 -2.6(3) . . . . ? C2 C15 C20 C19 176.77(16) . . . . ? C25 C23 C24 C28 -104.66(16) . . . . ? C31 C23 C24 C28 71.42(17) . . . . ? C25 C23 C24 C37 75.96(18) . . . . ? C31 C23 C24 C37 -107.96(16) . . . . ? C31 C23 C25 C27 0.1(2) . . . . ? C24 C23 C25 C27 175.76(15) . . . . ? C31 C23 C25 C26 179.79(14) . . . . ? C24 C23 C25 C26 -4.5(2) . . . . ? C37 C24 C28 C30 4.3(3) . . . . ? C23 C24 C28 C30 -174.99(15) . . . . ? C37 C24 C28 C29 -177.64(15) . . . . ? C23 C24 C28 C29 3.0(2) . . . . ? C25 C23 C31 C32 21.8(2) . . . . ? C24 C23 C31 C32 -153.92(14) . . . . ? C25 C23 C31 C36 -160.55(15) . . . . ? C24 C23 C31 C36 23.8(2) . . . . ? C36 C31 C32 C33 0.2(2) . . . . ? C23 C31 C32 C33 177.93(14) . . . . ? C31 C32 C33 C34 0.6(2) . . . . ? C32 C33 C34 N11 179.40(16) . . . . ? C32 C33 C34 C35 -0.3(2) . . . . ? N11 C34 C35 C36 179.62(17) . . . . ? C33 C34 C35 C36 -0.6(3) . . . . ? C34 C35 C36 C31 1.4(3) . . . . ? C32 C31 C36 C35 -1.2(2) . . . . ? C23 C31 C36 C35 -179.04(15) . . . . ? C28 C24 C37 C42 -164.25(16) . . . . ? C23 C24 C37 C42 15.0(2) . . . . ? C28 C24 C37 C38 15.0(3) . . . . ? C23 C24 C37 C38 -165.67(15) . . . . ? C42 C37 C38 C39 0.5(3) . . . . ? C24 C37 C38 C39 -178.81(16) . . . . ? C37 C38 C39 C40 -0.3(3) . . . . ? C43 N12 C40 C41 170.61(18) . . . . ? C44 N12 C40 C41 2.8(3) . . . . ? C43 N12 C40 C39 -10.1(3) . . . . ? C44 N12 C40 C39 -177.88(19) . . . . ? C38 C39 C40 N12 -179.33(17) . . . . ? C38 C39 C40 C41 0.0(3) . . . . ? N12 C40 C41 C42 179.41(16) . . . . ? C39 C40 C41 C42 0.1(3) . . . . ? C40 C41 C42 C37 0.1(3) . . . . ? C38 C37 C42 C41 -0.4(2) . . . . ? C24 C37 C42 C41 178.92(16) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 68.23 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.347 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.051 # Attachment '- 4b.cif' data_II _database_code_depnum_ccdc_archive 'CCDC 867036' #TrackingRef '- 4b.cif' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H11 N5' _chemical_formula_sum 'C20 H11 N5' _chemical_formula_weight 321.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I 41' _symmetry_space_group_name_Hall 'I 4bw' _symmetry_Int_Tables_number 80 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 'x, y, z' 2 '-y, x+1/2, z+1/4' 3 '-x+1/2, -y+1/2, z+1/2' 4 'y+1/2, -x, z+3/4' 5 'x+1/2, y+1/2, z+1/2' 6 '-y+1/2, x+1, z+3/4' 7 '-x+1, -y+1, z+1' 8 'y+1, -x+1/2, z+5/4' _cell_length_a 12.1481(3) _cell_length_b 12.1481(3) _cell_length_c 10.9626(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1617.83(8) _cell_formula_units_Z 4 _cell_measurement_temperature 193 _cell_measurement_reflns_used 13582 _cell_measurement_theta_min 5.2 _cell_measurement_theta_max 68.4 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.660 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.828 _exptl_absorpt_correction_T_max 0.936 _exptl_special_details ; ? ; _diffrn_ambient_temperature 193 _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 790 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 5.15 _diffrn_reflns_theta_max 68.25 _reflns_number_total 790 _reflns_number_gt 744 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0604P)^2^+0.7876P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0083(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 790 _refine_ls_number_parameters 119 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.081 _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 N1 N 0.1273(3) -0.3193(3) 0.6628(4) 0.0703(10) Uani 1 1 d . A . N2 N -0.1523(3) -0.1421(3) 0.5212(4) 0.0775(11) Uani 1 1 d . A . N3 N 0.4055(5) 0.0489(6) 1.0218(7) 0.076(2) Uani 0.50 1 d P A 1 H3A H 0.4040 0.1089 1.0668 0.091 Uiso 0.50 1 calc PR A 1 H3B H 0.4656 0.0086 1.0187 0.091 Uiso 0.50 1 calc PR A 1 C1 C 0.1388(3) -0.0251(2) 0.8034(3) 0.0468(8) Uani 1 1 d . A . C2 C 0.1356(3) 0.0611(3) 0.8884(4) 0.0586(10) Uani 1 1 d . . . H2 H 0.0713 0.1054 0.8938 0.070 Uiso 1 1 calc R . . C3 C 0.2225(3) 0.0830(3) 0.9639(4) 0.0633(11) Uani 1 1 d . A . H3 H 0.2183 0.1422 1.0202 0.076 Uiso 1 1 calc R . . C4 C 0.3165(3) 0.0191(3) 0.9583(4) 0.0647(11) Uani 1 1 d . . . H4 H 0.3767 0.0335 1.0113 0.078 Uiso 0.50 1 calc PR A 2 C5 C 0.3220(3) -0.0660(3) 0.8746(4) 0.0627(11) Uani 1 1 d . A . H5 H 0.3863 -0.1103 0.8704 0.075 Uiso 1 1 calc R . . C6 C 0.2357(3) -0.0872(3) 0.7977(4) 0.0556(9) Uani 1 1 d . . . H6 H 0.2418 -0.1448 0.7396 0.067 Uiso 1 1 calc R A . C7 C 0.0437(2) -0.0440(2) 0.7263(3) 0.0442(8) Uani 1 1 d . . . C8 C 0.0200(3) -0.1364(3) 0.6583(4) 0.0501(8) Uani 1 1 d . A . C9 C 0.0824(3) -0.2370(3) 0.6605(4) 0.0543(9) Uani 1 1 d . . . C10 C -0.0766(3) -0.1398(3) 0.5832(4) 0.0564(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.074(2) 0.0515(17) 0.085(3) -0.0085(18) -0.005(2) 0.0090(15) N2 0.084(2) 0.060(2) 0.088(3) -0.0050(19) -0.029(2) -0.0015(17) N3 0.058(4) 0.066(4) 0.103(6) -0.001(4) -0.030(4) -0.012(3) C1 0.0457(17) 0.0380(15) 0.0567(19) 0.0022(14) 0.0036(15) -0.0022(12) C2 0.0434(18) 0.0522(19) 0.080(3) -0.0119(19) 0.0028(17) 0.0009(14) C3 0.055(2) 0.059(2) 0.076(3) -0.0181(19) -0.005(2) -0.0016(16) C4 0.053(2) 0.062(2) 0.078(3) 0.001(2) -0.013(2) -0.0065(16) C5 0.0451(19) 0.058(2) 0.086(3) 0.001(2) -0.0073(18) 0.0057(15) C6 0.0475(18) 0.0471(18) 0.072(2) -0.0044(17) 0.0023(18) 0.0046(14) C7 0.0416(16) 0.0354(14) 0.0557(19) 0.0002(14) 0.0059(14) -0.0003(12) C8 0.0470(18) 0.0422(17) 0.0611(19) -0.0009(16) -0.0040(16) 0.0016(12) C9 0.059(2) 0.0384(17) 0.065(2) -0.0047(16) -0.0050(18) 0.0000(14) C10 0.058(2) 0.0401(17) 0.071(2) -0.0036(17) -0.008(2) 0.0002(15) _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 N1 C9 1.139(4) . ? N2 C10 1.144(5) . ? N3 C4 1.336(7) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? C1 C6 1.400(4) . ? C1 C2 1.402(5) . ? C1 C7 1.450(5) . ? C2 C3 1.367(5) . ? C2 H2 0.9500 . ? C3 C4 1.382(5) . ? C3 H3 0.9500 . ? C4 C5 1.385(6) . ? C4 H4 0.9500 . ? C5 C6 1.369(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.377(5) . ? C7 C7 1.508(5) 7_444 ? C8 C10 1.434(5) . ? C8 C9 1.439(4) . ? 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 C4 N3 H3A 120.0 . . ? C4 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C6 C1 C2 117.1(3) . . ? C6 C1 C7 123.9(3) . . ? C2 C1 C7 118.9(3) . . ? C3 C2 C1 121.7(3) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 120.2(4) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? N3 C4 C3 119.6(5) . . ? N3 C4 C5 120.6(5) . . ? C3 C4 C5 119.2(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 120.8(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 121.0(4) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? C8 C7 C1 127.7(3) . . ? C8 C7 C7 115.5(3) . 7_444 ? C1 C7 C7 116.6(3) . 7_444 ? C7 C8 C10 120.4(3) . . ? C7 C8 C9 125.0(3) . . ? C10 C8 C9 114.6(3) . . ? N1 C9 C8 176.9(4) . . ? N2 C10 C8 178.6(5) . . ? 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 -0.9(6) . . . . ? C7 C1 C2 C3 179.9(4) . . . . ? C1 C2 C3 C4 -0.4(6) . . . . ? C2 C3 C4 N3 172.1(5) . . . . ? C2 C3 C4 C5 0.8(6) . . . . ? N3 C4 C5 C6 -171.1(5) . . . . ? C3 C4 C5 C6 0.1(6) . . . . ? C4 C5 C6 C1 -1.5(6) . . . . ? C2 C1 C6 C5 1.8(5) . . . . ? C7 C1 C6 C5 -179.0(3) . . . . ? C6 C1 C7 C8 16.7(6) . . . . ? C2 C1 C7 C8 -164.1(3) . . . . ? C6 C1 C7 C7 -167.8(3) . . . 7_444 ? C2 C1 C7 C7 11.5(4) . . . 7_444 ? C1 C7 C8 C10 -177.8(3) . . . . ? C7 C7 C8 C10 6.6(5) 7_444 . . . ? C1 C7 C8 C9 6.0(6) . . . . ? C7 C7 C8 C9 -169.6(3) 7_444 . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 68.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.156 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.045