# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_090929_0m #TrackingRef '19186_web_deposit_cif_file_0_Tsu-HuiSu_1365010386.BIQF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C53 H32 N6' _chemical_formula_weight 752.85 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 8.61740(10) _cell_length_b 11.3389(2) _cell_length_c 19.7751(3) _cell_angle_alpha 92.9490(10) _cell_angle_beta 98.4620(10) _cell_angle_gamma 94.4270(10) _cell_volume 1901.66(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9946 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Tabullar _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7212 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 28103 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.04 _diffrn_reflns_theta_max 26.37 _reflns_number_total 7758 _reflns_number_gt 6121 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'Shelxtl-97 (Sheldrick, 2008)' _computing_structure_refinement 'Shelxtl-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _computing_publication_material 'Bruker APEX2' _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^+0.2216P] 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 7758 _refine_ls_number_parameters 532 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1164 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.47316(14) -0.02578(10) 0.19457(6) 0.0354(3) Uani 1 1 d . . . C2 C 0.41574(15) -0.05710(11) 0.11805(6) 0.0390(3) Uani 1 1 d . . . C3 C 0.33074(17) 0.00839(13) 0.07114(7) 0.0508(3) Uani 1 1 d . . . H3 H 0.2978 0.0809 0.0847 0.061 Uiso 1 1 calc R . . C4 C 0.2952(2) -0.03587(16) 0.00327(8) 0.0614(4) Uani 1 1 d . . . H4 H 0.2366 0.0069 -0.0287 0.074 Uiso 1 1 calc R . . C5 C 0.3458(2) -0.14233(16) -0.01691(8) 0.0647(5) Uani 1 1 d . . . H5 H 0.3222 -0.1702 -0.0626 0.078 Uiso 1 1 calc R . . C6 C 0.4307(2) -0.20805(14) 0.02928(7) 0.0600(4) Uani 1 1 d . . . H6 H 0.4646 -0.2799 0.0152 0.072 Uiso 1 1 calc R . . C7 C 0.46527(16) -0.16548(12) 0.09769(7) 0.0439(3) Uani 1 1 d . . . C8 C 0.54771(16) -0.21689(11) 0.15780(7) 0.0434(3) Uani 1 1 d . . . C9 C 0.61212(19) -0.32503(13) 0.16560(9) 0.0574(4) Uani 1 1 d . . . H9 H 0.6116 -0.3775 0.1278 0.069 Uiso 1 1 calc R . . C10 C 0.67671(18) -0.35333(13) 0.23004(9) 0.0605(4) Uani 1 1 d . . . H10 H 0.7212 -0.4251 0.2355 0.073 Uiso 1 1 calc R . . C11 C 0.67652(17) -0.27709(13) 0.28668(8) 0.0543(4) Uani 1 1 d . . . H11 H 0.7187 -0.2985 0.3299 0.065 Uiso 1 1 calc R . . C12 C 0.61383(16) -0.16867(12) 0.27949(7) 0.0451(3) Uani 1 1 d . . . H12 H 0.6138 -0.1171 0.3176 0.054 Uiso 1 1 calc R . . C13 C 0.55144(14) -0.13832(10) 0.21498(6) 0.0371(3) Uani 1 1 d . . . C14 C 0.59190(14) 0.08380(10) 0.20046(6) 0.0359(3) Uani 1 1 d . . . C15 C 0.75134(15) 0.07210(11) 0.20233(7) 0.0421(3) Uani 1 1 d . . . H15 H 0.7878 -0.0028 0.2052 0.050 Uiso 1 1 calc R . . C16 C 0.85783(16) 0.16942(11) 0.20010(7) 0.0447(3) Uani 1 1 d . . . H16 H 0.9642 0.1592 0.2011 0.054 Uiso 1 1 calc R . . C17 C 0.80630(15) 0.28096(11) 0.19646(6) 0.0405(3) Uani 1 1 d . . . C18 C 0.64770(16) 0.29502(11) 0.19540(7) 0.0464(3) Uani 1 1 d . . . H18 H 0.6121 0.3703 0.1935 0.056 Uiso 1 1 calc R . . C19 C 0.54210(16) 0.19738(11) 0.19718(7) 0.0439(3) Uani 1 1 d . . . H19 H 0.4358 0.2079 0.1962 0.053 Uiso 1 1 calc R . . C20 C 0.90595(16) 0.46091(11) 0.14253(7) 0.0440(3) Uani 1 1 d . . . C21 C 0.82670(18) 0.54306(12) 0.04438(8) 0.0521(4) Uani 1 1 d . . . C22 C 0.7259(2) 0.54358(16) -0.01844(9) 0.0693(5) Uani 1 1 d . . . H22 H 0.6418 0.4860 -0.0294 0.083 Uiso 1 1 calc R . . C23 C 0.7509(3) 0.62828(19) -0.06347(10) 0.0828(6) Uani 1 1 d . . . H23 H 0.6841 0.6273 -0.1050 0.099 Uiso 1 1 calc R . . C24 C 0.8757(3) 0.71608(19) -0.04760(12) 0.0856(6) Uani 1 1 d . . . H24 H 0.8919 0.7727 -0.0788 0.103 Uiso 1 1 calc R . . C25 C 0.9733(2) 0.71947(17) 0.01287(11) 0.0774(5) Uani 1 1 d . . . H25 H 1.0545 0.7795 0.0233 0.093 Uiso 1 1 calc R . . C26 C 0.95299(19) 0.63294(13) 0.06010(9) 0.0558(4) Uani 1 1 d . . . C27 C 1.03625(16) 0.54961(11) 0.15886(7) 0.0471(3) Uani 1 1 d . . . C28 C 1.12796(17) 0.51973(13) 0.22145(8) 0.0517(3) Uani 1 1 d . . . C29 C 1.2662(2) 0.56974(16) 0.26031(10) 0.0687(5) Uani 1 1 d . . . H29 H 1.3170 0.6389 0.2479 0.082 Uiso 1 1 calc R . . C30 C 1.3271(2) 0.51508(19) 0.31771(11) 0.0833(6) Uani 1 1 d . . . H30 H 1.4203 0.5474 0.3443 0.100 Uiso 1 1 calc R . . C31 C 1.2505(2) 0.41198(18) 0.33629(10) 0.0757(5) Uani 1 1 d . . . H31 H 1.2938 0.3769 0.3754 0.091 Uiso 1 1 calc R . . C32 C 1.11248(18) 0.36007(15) 0.29863(8) 0.0589(4) Uani 1 1 d . . . H32 H 1.0625 0.2909 0.3114 0.071 Uiso 1 1 calc R . . C33 C 1.05153(16) 0.41524(12) 0.24110(7) 0.0460(3) Uani 1 1 d . . . C34 C 0.33983(14) -0.01504(10) 0.23713(6) 0.0359(3) Uani 1 1 d . . . C35 C 0.36219(16) 0.05036(12) 0.29986(7) 0.0475(3) Uani 1 1 d . . . H35 H 0.4531 0.1011 0.3125 0.057 Uiso 1 1 calc R . . C36 C 0.25094(17) 0.04094(13) 0.34363(7) 0.0500(3) Uani 1 1 d . . . H36 H 0.2676 0.0846 0.3855 0.060 Uiso 1 1 calc R . . C37 C 0.11573(15) -0.03330(11) 0.32489(6) 0.0401(3) Uani 1 1 d . . . C38 C 0.08863(15) -0.09584(12) 0.26201(7) 0.0430(3) Uani 1 1 d . . . H38 H -0.0043 -0.1441 0.2489 0.052 Uiso 1 1 calc R . . C39 C 0.20027(15) -0.08638(11) 0.21862(6) 0.0408(3) Uani 1 1 d . . . H39 H 0.1815 -0.1286 0.1762 0.049 Uiso 1 1 calc R . . C40 C -0.08787(14) 0.02578(11) 0.39702(6) 0.0385(3) Uani 1 1 d . . . C41 C -0.21044(15) 0.19030(12) 0.41141(7) 0.0443(3) Uani 1 1 d . . . C42 C -0.23868(18) 0.30782(13) 0.39643(9) 0.0586(4) Uani 1 1 d . . . H42 H -0.1860 0.3453 0.3646 0.070 Uiso 1 1 calc R . . C43 C -0.34230(19) 0.36676(15) 0.42813(10) 0.0689(5) Uani 1 1 d . . . H43 H -0.3589 0.4444 0.4180 0.083 Uiso 1 1 calc R . . C44 C -0.4239(2) 0.31235(16) 0.47555(10) 0.0698(5) Uani 1 1 d . . . H44 H -0.4936 0.3542 0.4970 0.084 Uiso 1 1 calc R . . C45 C -0.40238(18) 0.19839(15) 0.49070(9) 0.0608(4) Uani 1 1 d . . . H45 H -0.4584 0.1626 0.5220 0.073 Uiso 1 1 calc R . . C46 C -0.29543(15) 0.13431(12) 0.45912(7) 0.0458(3) Uani 1 1 d . . . C47 C -0.17338(14) -0.03245(11) 0.44500(6) 0.0389(3) Uani 1 1 d . . . C48 C -0.12513(15) -0.15120(11) 0.44824(6) 0.0405(3) Uani 1 1 d . . . C49 C -0.16713(17) -0.24827(13) 0.48381(7) 0.0507(3) Uani 1 1 d . . . H49 H -0.2386 -0.2428 0.5146 0.061 Uiso 1 1 calc R . . C50 C -0.1009(2) -0.35268(14) 0.47262(8) 0.0593(4) Uani 1 1 d . . . H50 H -0.1286 -0.4187 0.4957 0.071 Uiso 1 1 calc R . . C51 C 0.00710(19) -0.36068(13) 0.42723(8) 0.0586(4) Uani 1 1 d . . . H51 H 0.0496 -0.4325 0.4203 0.070 Uiso 1 1 calc R . . C52 C 0.05304(17) -0.26529(13) 0.39220(8) 0.0511(3) Uani 1 1 d . . . H52 H 0.1269 -0.2710 0.3626 0.061 Uiso 1 1 calc R . . C53 C -0.01514(15) -0.16068(11) 0.40288(6) 0.0413(3) Uani 1 1 d . . . N1 N 0.91471(13) 0.38209(10) 0.19365(6) 0.0467(3) Uani 1 1 d . . . N2 N 0.80012(14) 0.45532(10) 0.08782(6) 0.0495(3) Uani 1 1 d . . . N3 N 1.05954(15) 0.63670(11) 0.11938(7) 0.0599(3) Uani 1 1 d . . . N4 N 0.00735(13) -0.05305(9) 0.37260(5) 0.0428(3) Uani 1 1 d . . . N5 N -0.10266(13) 0.13440(10) 0.37953(5) 0.0435(3) Uani 1 1 d . . . N6 N -0.27616(13) 0.01998(10) 0.47604(6) 0.0457(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0391(6) 0.0306(6) 0.0368(6) 0.0019(5) 0.0097(5) -0.0017(5) C2 0.0414(7) 0.0380(7) 0.0377(6) 0.0026(5) 0.0122(5) -0.0073(6) C3 0.0547(8) 0.0504(8) 0.0467(8) 0.0083(6) 0.0084(6) -0.0034(7) C4 0.0638(10) 0.0732(11) 0.0437(8) 0.0150(8) 0.0031(7) -0.0137(8) C5 0.0787(11) 0.0743(11) 0.0371(7) -0.0026(8) 0.0125(7) -0.0222(9) C6 0.0767(11) 0.0558(9) 0.0476(8) -0.0108(7) 0.0237(8) -0.0117(8) C7 0.0497(8) 0.0412(7) 0.0420(7) -0.0022(6) 0.0182(6) -0.0074(6) C8 0.0451(7) 0.0353(7) 0.0516(8) -0.0010(6) 0.0179(6) -0.0025(6) C9 0.0637(9) 0.0407(8) 0.0702(10) -0.0060(7) 0.0206(8) 0.0066(7) C10 0.0540(9) 0.0391(8) 0.0886(12) 0.0052(8) 0.0089(8) 0.0087(7) C11 0.0479(8) 0.0434(8) 0.0685(10) 0.0122(7) -0.0020(7) -0.0014(6) C12 0.0459(7) 0.0381(7) 0.0491(7) 0.0023(6) 0.0032(6) -0.0034(6) C13 0.0364(6) 0.0309(6) 0.0443(7) 0.0024(5) 0.0108(5) -0.0036(5) C14 0.0410(7) 0.0323(6) 0.0346(6) 0.0016(5) 0.0094(5) -0.0022(5) C15 0.0416(7) 0.0335(6) 0.0521(7) 0.0067(6) 0.0096(6) 0.0013(5) C16 0.0373(7) 0.0412(7) 0.0559(8) 0.0067(6) 0.0095(6) -0.0012(6) C17 0.0438(7) 0.0346(6) 0.0420(7) 0.0030(5) 0.0083(5) -0.0075(6) C18 0.0500(8) 0.0296(6) 0.0603(8) 0.0018(6) 0.0133(6) 0.0007(6) C19 0.0392(7) 0.0342(7) 0.0595(8) 0.0017(6) 0.0138(6) 0.0002(6) C20 0.0481(8) 0.0341(7) 0.0516(8) 0.0025(6) 0.0151(6) 0.0008(6) C21 0.0627(9) 0.0425(8) 0.0573(9) 0.0082(7) 0.0231(7) 0.0135(7) C22 0.0844(12) 0.0618(10) 0.0648(10) 0.0135(8) 0.0120(9) 0.0170(9) C23 0.1016(15) 0.0860(14) 0.0720(12) 0.0308(10) 0.0258(11) 0.0378(13) C24 0.0926(15) 0.0831(14) 0.1013(15) 0.0514(12) 0.0503(13) 0.0378(12) C25 0.0743(12) 0.0653(11) 0.1059(15) 0.0395(11) 0.0405(11) 0.0166(9) C26 0.0576(9) 0.0451(8) 0.0729(10) 0.0156(7) 0.0305(8) 0.0102(7) C27 0.0465(7) 0.0346(7) 0.0629(9) 0.0040(6) 0.0207(7) -0.0031(6) C28 0.0462(8) 0.0437(8) 0.0654(9) 0.0030(7) 0.0149(7) -0.0061(6) C29 0.0542(9) 0.0604(10) 0.0872(12) 0.0086(9) 0.0076(9) -0.0192(8) C30 0.0568(10) 0.0898(14) 0.0927(14) 0.0119(11) -0.0106(10) -0.0227(10) C31 0.0593(10) 0.0866(13) 0.0742(11) 0.0183(10) -0.0073(9) -0.0135(10) C32 0.0521(9) 0.0604(9) 0.0624(9) 0.0109(8) 0.0076(7) -0.0086(7) C33 0.0416(7) 0.0426(7) 0.0528(8) 0.0009(6) 0.0093(6) -0.0059(6) C34 0.0392(6) 0.0311(6) 0.0382(6) 0.0032(5) 0.0096(5) 0.0005(5) C35 0.0469(7) 0.0476(8) 0.0465(7) -0.0087(6) 0.0147(6) -0.0130(6) C36 0.0560(8) 0.0503(8) 0.0432(7) -0.0101(6) 0.0172(6) -0.0084(7) C37 0.0410(7) 0.0388(7) 0.0432(7) 0.0055(5) 0.0147(5) 0.0036(6) C38 0.0364(7) 0.0449(7) 0.0470(7) 0.0022(6) 0.0081(5) -0.0042(6) C39 0.0415(7) 0.0416(7) 0.0386(6) -0.0027(5) 0.0085(5) -0.0027(6) C40 0.0377(7) 0.0409(7) 0.0370(6) 0.0022(5) 0.0082(5) 0.0000(6) C41 0.0393(7) 0.0444(7) 0.0484(7) 0.0019(6) 0.0041(6) 0.0039(6) C42 0.0533(9) 0.0491(8) 0.0741(10) 0.0115(8) 0.0078(8) 0.0078(7) C43 0.0530(9) 0.0505(9) 0.1024(14) 0.0036(9) 0.0044(9) 0.0140(8) C44 0.0494(9) 0.0629(11) 0.0981(13) -0.0103(10) 0.0145(9) 0.0147(8) C45 0.0461(8) 0.0649(10) 0.0741(10) -0.0029(8) 0.0191(7) 0.0086(7) C46 0.0377(7) 0.0478(8) 0.0510(8) -0.0009(6) 0.0063(6) 0.0020(6) C47 0.0366(6) 0.0429(7) 0.0365(6) 0.0023(5) 0.0062(5) -0.0029(6) C48 0.0395(7) 0.0428(7) 0.0388(6) 0.0055(5) 0.0061(5) -0.0016(6) C49 0.0524(8) 0.0515(8) 0.0482(8) 0.0126(6) 0.0097(6) -0.0052(7) C50 0.0679(10) 0.0460(8) 0.0633(9) 0.0190(7) 0.0058(8) -0.0023(7) C51 0.0634(10) 0.0432(8) 0.0684(10) 0.0093(7) 0.0028(8) 0.0092(7) C52 0.0501(8) 0.0484(8) 0.0563(8) 0.0051(7) 0.0099(7) 0.0090(7) C53 0.0393(7) 0.0404(7) 0.0434(7) 0.0056(6) 0.0050(5) -0.0008(6) N1 0.0480(6) 0.0382(6) 0.0522(7) 0.0072(5) 0.0068(5) -0.0091(5) N2 0.0576(7) 0.0383(6) 0.0534(7) 0.0058(5) 0.0114(6) 0.0023(5) N3 0.0573(8) 0.0442(7) 0.0827(9) 0.0151(6) 0.0250(7) -0.0013(6) N4 0.0456(6) 0.0393(6) 0.0474(6) 0.0075(5) 0.0187(5) 0.0028(5) N5 0.0455(6) 0.0420(6) 0.0441(6) 0.0068(5) 0.0098(5) 0.0019(5) N6 0.0413(6) 0.0514(7) 0.0459(6) 0.0021(5) 0.0133(5) 0.0012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C34 1.5293(17) . ? C1 C13 1.5336(17) . ? C1 C2 1.5354(17) . ? C1 C14 1.5356(16) . ? C2 C3 1.3796(19) . ? C2 C7 1.3912(18) . ? C3 C4 1.390(2) . ? C3 H3 0.9300 . ? C4 C5 1.375(2) . ? C4 H4 0.9300 . ? C5 C6 1.372(2) . ? C5 H5 0.9300 . ? C6 C7 1.3941(19) . ? C6 H6 0.9300 . ? C7 C8 1.464(2) . ? C8 C9 1.3909(19) . ? C8 C13 1.3979(17) . ? C9 C10 1.378(2) . ? C9 H9 0.9300 . ? C10 C11 1.379(2) . ? C10 H10 0.9300 . ? C11 C12 1.3861(19) . ? C11 H11 0.9300 . ? C12 C13 1.3810(18) . ? C12 H12 0.9300 . ? C14 C15 1.3858(18) . ? C14 C19 1.3903(17) . ? C15 C16 1.3865(18) . ? C15 H15 0.9300 . ? C16 C17 1.3743(18) . ? C16 H16 0.9300 . ? C17 C18 1.3854(19) . ? C17 N1 1.4308(16) . ? C18 C19 1.3831(18) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 N2 1.3038(18) . ? C20 N1 1.3810(17) . ? C20 C27 1.4361(19) . ? C21 N2 1.3751(18) . ? C21 C22 1.408(2) . ? C21 C26 1.420(2) . ? C22 C23 1.369(2) . ? C22 H22 0.9300 . ? C23 C24 1.396(3) . ? C23 H23 0.9300 . ? C24 C25 1.354(3) . ? C24 H24 0.9300 . ? C25 C26 1.408(2) . ? C25 H25 0.9300 . ? C26 N3 1.375(2) . ? C27 N3 1.3114(18) . ? C27 C28 1.438(2) . ? C28 C29 1.383(2) . ? C28 C33 1.4110(19) . ? C29 C30 1.377(3) . ? C29 H29 0.9300 . ? C30 C31 1.391(3) . ? C30 H30 0.9300 . ? C31 C32 1.379(2) . ? C31 H31 0.9300 . ? C32 C33 1.382(2) . ? C32 H32 0.9300 . ? C33 N1 1.4077(17) . ? C34 C39 1.3873(17) . ? C34 C35 1.3925(17) . ? C35 C36 1.3848(18) . ? C35 H35 0.9300 . ? C36 C37 1.3759(19) . ? C36 H36 0.9300 . ? C37 C38 1.3790(18) . ? C37 N4 1.4358(15) . ? C38 C39 1.3820(18) . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 N5 1.3069(16) . ? C40 N4 1.3751(16) . ? C40 C47 1.4402(17) . ? C41 N5 1.3725(17) . ? C41 C42 1.4114(19) . ? C41 C46 1.422(2) . ? C42 C43 1.360(2) . ? C42 H42 0.9300 . ? C43 C44 1.393(3) . ? C43 H43 0.9300 . ? C44 C45 1.362(2) . ? C44 H44 0.9300 . ? C45 C46 1.412(2) . ? C45 H45 0.9300 . ? C46 N6 1.3717(17) . ? C47 N6 1.3108(16) . ? C47 C48 1.4413(18) . ? C48 C49 1.3895(18) . ? C48 C53 1.4038(18) . ? C49 C50 1.375(2) . ? C49 H49 0.9300 . ? C50 C51 1.389(2) . ? C50 H50 0.9300 . ? C51 C52 1.378(2) . ? C51 H51 0.9300 . ? C52 C53 1.3839(19) . ? C52 H52 0.9300 . ? C53 N4 1.3993(16) . ? 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 C34 C1 C13 106.67(9) . . ? C34 C1 C2 113.72(10) . . ? C13 C1 C2 100.62(9) . . ? C34 C1 C14 114.86(9) . . ? C13 C1 C14 112.54(10) . . ? C2 C1 C14 107.61(9) . . ? C3 C2 C7 120.49(12) . . ? C3 C2 C1 128.58(12) . . ? C7 C2 C1 110.90(11) . . ? C2 C3 C4 118.90(15) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 120.51(15) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C6 C5 C4 121.07(14) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.00(15) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C2 C7 C6 120.02(14) . . ? C2 C7 C8 108.84(11) . . ? C6 C7 C8 131.13(13) . . ? C9 C8 C13 119.73(13) . . ? C9 C8 C7 131.55(13) . . ? C13 C8 C7 108.68(11) . . ? C10 C9 C8 119.09(14) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 121.12(14) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C11 C12 120.32(14) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 119.09(13) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C8 120.61(12) . . ? C12 C13 C1 128.55(11) . . ? C8 C13 C1 110.78(11) . . ? C15 C14 C19 117.55(11) . . ? C15 C14 C1 120.92(11) . . ? C19 C14 C1 121.22(11) . . ? C14 C15 C16 121.60(12) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C17 C16 C15 120.02(12) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 119.41(12) . . ? C16 C17 N1 120.63(12) . . ? C18 C17 N1 119.96(12) . . ? C19 C18 C17 120.20(12) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C14 121.21(12) . . ? C18 C19 H19 119.4 . . ? C14 C19 H19 119.4 . . ? N2 C20 N1 126.35(12) . . ? N2 C20 C27 125.29(13) . . ? N1 C20 C27 108.34(12) . . ? N2 C21 C22 118.94(15) . . ? N2 C21 C26 122.56(14) . . ? C22 C21 C26 118.50(14) . . ? C23 C22 C21 120.45(19) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 120.6(2) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C25 C24 C23 120.53(17) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 120.59(19) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? N3 C26 C25 118.49(16) . . ? N3 C26 C21 122.16(13) . . ? C25 C26 C21 119.32(17) . . ? N3 C27 C20 122.39(14) . . ? N3 C27 C28 130.29(13) . . ? C20 C27 C28 107.29(12) . . ? C29 C28 C33 120.09(15) . . ? C29 C28 C27 133.45(14) . . ? C33 C28 C27 106.43(12) . . ? C30 C29 C28 118.66(15) . . ? C30 C29 H29 120.7 . . ? C28 C29 H29 120.7 . . ? C29 C30 C31 120.53(16) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C32 C31 C30 122.15(17) . . ? C32 C31 H31 118.9 . . ? C30 C31 H31 118.9 . . ? C31 C32 C33 117.17(15) . . ? C31 C32 H32 121.4 . . ? C33 C32 H32 121.4 . . ? C32 C33 N1 129.29(13) . . ? C32 C33 C28 121.39(13) . . ? N1 C33 C28 109.32(12) . . ? C39 C34 C35 118.08(11) . . ? C39 C34 C1 119.32(10) . . ? C35 C34 C1 121.83(11) . . ? C36 C35 C34 120.91(12) . . ? C36 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C37 C36 C35 119.76(12) . . ? C37 C36 H36 120.1 . . ? C35 C36 H36 120.1 . . ? C36 C37 C38 120.31(12) . . ? C36 C37 N4 120.20(11) . . ? C38 C37 N4 119.32(11) . . ? C37 C38 C39 119.66(12) . . ? C37 C38 H38 120.2 . . ? C39 C38 H38 120.2 . . ? C38 C39 C34 121.20(11) . . ? C38 C39 H39 119.4 . . ? C34 C39 H39 119.4 . . ? N5 C40 N4 126.85(11) . . ? N5 C40 C47 124.85(12) . . ? N4 C40 C47 108.28(11) . . ? N5 C41 C42 119.03(13) . . ? N5 C41 C46 122.52(12) . . ? C42 C41 C46 118.45(13) . . ? C43 C42 C41 120.60(16) . . ? C43 C42 H42 119.7 . . ? C41 C42 H42 119.7 . . ? C42 C43 C44 120.88(16) . . ? C42 C43 H43 119.6 . . ? C44 C43 H43 119.6 . . ? C45 C44 C43 120.55(16) . . ? C45 C44 H44 119.7 . . ? C43 C44 H44 119.7 . . ? C44 C45 C46 120.33(16) . . ? C44 C45 H45 119.8 . . ? C46 C45 H45 119.8 . . ? N6 C46 C45 118.65(13) . . ? N6 C46 C41 122.17(12) . . ? C45 C46 C41 119.18(14) . . ? N6 C47 C40 122.46(12) . . ? N6 C47 C48 130.59(12) . . ? C40 C47 C48 106.94(11) . . ? C49 C48 C53 119.86(12) . . ? C49 C48 C47 133.84(12) . . ? C53 C48 C47 106.29(11) . . ? C50 C49 C48 118.63(14) . . ? C50 C49 H49 120.7 . . ? C48 C49 H49 120.7 . . ? C49 C50 C51 120.74(14) . . ? C49 C50 H50 119.6 . . ? C51 C50 H50 119.6 . . ? C52 C51 C50 121.88(14) . . ? C52 C51 H51 119.1 . . ? C50 C51 H51 119.1 . . ? C51 C52 C53 117.33(14) . . ? C51 C52 H52 121.3 . . ? C53 C52 H52 121.3 . . ? C52 C53 N4 128.68(12) . . ? C52 C53 C48 121.55(12) . . ? N4 C53 C48 109.76(11) . . ? C20 N1 C33 108.56(11) . . ? C20 N1 C17 125.70(11) . . ? C33 N1 C17 125.70(11) . . ? C20 N2 C21 113.07(12) . . ? C27 N3 C26 114.45(13) . . ? C40 N4 C53 108.72(10) . . ? C40 N4 C37 127.96(10) . . ? C53 N4 C37 123.31(10) . . ? C40 N5 C41 113.37(11) . . ? C47 N6 C46 114.63(11) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.221 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 932437' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mo_101150lt_0m #TrackingRef '19187_web_deposit_cif_file_1_Tsu-HuiSu_1365010386.BIQTP.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H28 N6' _chemical_formula_weight 664.74 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' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8757(8) _cell_length_b 11.0628(15) _cell_length_c 12.9069(17) _cell_angle_alpha 75.270(3) _cell_angle_beta 78.072(3) _cell_angle_gamma 87.700(3) _cell_volume 793.81(18) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5568 _cell_measurement_theta_min 2.8283 _cell_measurement_theta_max 26.4654 _exptl_crystal_description lump _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 346 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8784 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 12263 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 26.53 _reflns_number_total 3266 _reflns_number_gt 2818 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0274P)^2^+3.1709P] 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 3266 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.1794 _refine_ls_wR_factor_gt 0.1748 _refine_ls_goodness_of_fit_ref 1.081 _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 0.0390(4) 0.5841(2) 0.3290(2) 0.0159(5) Uani 1 1 d . . . N2 N -0.0861(4) 0.7404(2) 0.0716(2) 0.0158(5) Uani 1 1 d . . . N3 N 0.2423(4) 0.6080(2) 0.0994(2) 0.0159(5) Uani 1 1 d . . . C1 C 0.5636(5) 0.3985(3) 0.3478(3) 0.0200(6) Uani 1 1 d . . . H1 H 0.6405 0.3517 0.4028 0.024 Uiso 1 1 calc R . . C2 C 0.3552(6) 0.4544(3) 0.3773(3) 0.0196(6) Uani 1 1 d . . . H2 H 0.2876 0.4451 0.4524 0.024 Uiso 1 1 calc R . . C3 C 0.2415(5) 0.5257(3) 0.2959(2) 0.0154(6) Uani 1 1 d . . . C4 C -0.0509(5) 0.6520(3) 0.2487(2) 0.0148(6) Uani 1 1 d . . . C5 C 0.0527(5) 0.6630(3) 0.1347(2) 0.0144(6) Uani 1 1 d . . . C6 C -0.0503(5) 0.7789(3) -0.0457(2) 0.0158(6) Uani 1 1 d . . . C7 C -0.2182(5) 0.7496(3) -0.0969(2) 0.0176(6) Uani 1 1 d . . . H7 H -0.3465 0.6970 -0.0557 0.021 Uiso 1 1 calc R . . C8 C -0.1976(5) 0.7979(3) -0.2090(2) 0.0166(6) Uani 1 1 d . . . H8 H -0.3133 0.7781 -0.2439 0.020 Uiso 1 1 calc R . . C9 C -0.0090(5) 0.8754(3) -0.2715(2) 0.0152(6) Uani 1 1 d . . . C10 C 0.0001(5) 0.9359(3) -0.3894(2) 0.0147(6) Uani 1 1 d . . . C11 C 0.1475(8) 1.0353(5) -0.4443(3) 0.0526(14) Uani 1 1 d . . . H11 H 0.2540 1.0614 -0.4079 0.063 Uiso 1 1 calc R . . C12 C -0.1447(8) 0.9013(5) -0.4480(3) 0.0536(14) Uani 1 1 d . . . H12 H -0.2468 0.8317 -0.4139 0.064 Uiso 1 1 calc R . . C13 C 0.1621(5) 0.8986(3) -0.2182(2) 0.0195(6) Uani 1 1 d . . . H13 H 0.2951 0.9476 -0.2592 0.023 Uiso 1 1 calc R . . C14 C 0.1413(5) 0.8511(3) -0.1060(3) 0.0192(6) Uani 1 1 d . . . H14 H 0.2588 0.8683 -0.0708 0.023 Uiso 1 1 calc R . . C15 C -0.2584(5) 0.7272(3) 0.2511(2) 0.0165(6) Uani 1 1 d . . . C16 C -0.2731(5) 0.7792(3) 0.1413(2) 0.0154(6) Uani 1 1 d . . . C17 C -0.4548(5) 0.8576(3) 0.1142(3) 0.0173(6) Uani 1 1 d . . . H17 H -0.4634 0.8936 0.0400 0.021 Uiso 1 1 calc R . . C18 C -0.6228(5) 0.8812(3) 0.1992(3) 0.0210(7) Uani 1 1 d . . . H18 H -0.7489 0.9340 0.1827 0.025 Uiso 1 1 calc R . . C19 C -0.6109(6) 0.8288(3) 0.3090(3) 0.0232(7) Uani 1 1 d . . . H19 H -0.7288 0.8463 0.3656 0.028 Uiso 1 1 calc R . . C20 C -0.4289(6) 0.7519(3) 0.3355(3) 0.0199(6) Uani 1 1 d . . . H20 H -0.4202 0.7167 0.4098 0.024 Uiso 1 1 calc R . . C21 C 0.3422(5) 0.5379(3) 0.1830(2) 0.0153(6) Uani 1 1 d . . . C22 C 0.5556(5) 0.4777(3) 0.1554(2) 0.0172(6) Uani 1 1 d . . . H22 H 0.6237 0.4839 0.0807 0.021 Uiso 1 1 calc R . . C23 C 0.6641(5) 0.4104(3) 0.2360(3) 0.0191(6) Uani 1 1 d . . . H23 H 0.8081 0.3714 0.2166 0.023 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 N1 0.0165(12) 0.0166(12) 0.0142(12) -0.0026(10) -0.0038(10) -0.0014(10) N2 0.0166(12) 0.0189(13) 0.0114(12) -0.0021(10) -0.0042(10) 0.0019(10) N3 0.0172(12) 0.0149(12) 0.0148(12) -0.0022(10) -0.0029(10) -0.0014(10) C1 0.0208(16) 0.0162(14) 0.0215(16) 0.0012(12) -0.0090(12) 0.0020(12) C2 0.0229(16) 0.0205(15) 0.0140(14) -0.0004(12) -0.0050(12) -0.0011(12) C3 0.0148(14) 0.0155(14) 0.0148(14) -0.0013(11) -0.0030(11) -0.0019(11) C4 0.0141(14) 0.0154(14) 0.0145(14) -0.0023(11) -0.0029(11) -0.0029(11) C5 0.0150(14) 0.0153(14) 0.0133(14) -0.0023(11) -0.0053(11) -0.0013(11) C6 0.0187(15) 0.0162(14) 0.0115(14) -0.0018(11) -0.0036(11) 0.0024(11) C7 0.0179(15) 0.0168(14) 0.0165(15) -0.0004(11) -0.0038(12) -0.0027(11) C8 0.0156(14) 0.0184(14) 0.0167(15) -0.0023(11) -0.0077(12) -0.0008(11) C9 0.0177(14) 0.0139(13) 0.0140(14) -0.0039(11) -0.0029(11) 0.0011(11) C10 0.0162(14) 0.0144(13) 0.0118(13) -0.0018(11) -0.0015(11) 0.0024(11) C11 0.053(3) 0.074(3) 0.025(2) 0.017(2) -0.0221(19) -0.045(2) C12 0.056(3) 0.072(3) 0.025(2) 0.019(2) -0.0208(19) -0.048(2) C13 0.0176(15) 0.0231(15) 0.0154(15) 0.0009(12) -0.0039(12) -0.0055(12) C14 0.0183(15) 0.0224(15) 0.0177(15) -0.0035(12) -0.0068(12) -0.0030(12) C15 0.0174(15) 0.0152(14) 0.0156(14) -0.0015(11) -0.0029(11) -0.0023(11) C16 0.0148(14) 0.0144(14) 0.0166(14) -0.0026(11) -0.0035(11) -0.0032(11) C17 0.0192(15) 0.0152(14) 0.0196(15) -0.0049(12) -0.0086(12) 0.0014(11) C18 0.0161(15) 0.0162(14) 0.0323(18) -0.0074(13) -0.0070(13) 0.0018(12) C19 0.0209(16) 0.0206(16) 0.0260(17) -0.0076(13) 0.0017(13) 0.0001(13) C20 0.0217(16) 0.0193(15) 0.0170(15) -0.0039(12) -0.0009(12) -0.0003(12) C21 0.0166(14) 0.0137(14) 0.0152(14) -0.0016(11) -0.0040(11) -0.0025(11) C22 0.0167(14) 0.0178(14) 0.0171(15) -0.0048(12) -0.0025(12) -0.0014(11) C23 0.0165(15) 0.0165(14) 0.0238(16) -0.0041(12) -0.0043(12) -0.0006(11) _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 C4 1.311(4) . ? N1 C3 1.373(4) . ? N2 C5 1.387(4) . ? N2 C16 1.397(4) . ? N2 C6 1.438(4) . ? N3 C5 1.302(4) . ? N3 C21 1.381(4) . ? C1 C2 1.375(5) . ? C1 C23 1.416(4) . ? C1 H1 0.9500 . ? C2 C3 1.413(4) . ? C2 H2 0.9500 . ? C3 C21 1.429(4) . ? C4 C5 1.447(4) . ? C4 C15 1.448(4) . ? C6 C14 1.380(4) . ? C6 C7 1.385(4) . ? C7 C8 1.390(4) . ? C7 H7 0.9500 . ? C8 C9 1.403(4) . ? C8 H8 0.9500 . ? C9 C13 1.396(4) . ? C9 C10 1.489(4) . ? C10 C12 1.372(5) . ? C10 C11 1.374(5) . ? C11 C12 1.391(5) 2_574 ? C11 H11 0.9500 . ? C12 C11 1.391(5) 2_574 ? C12 H12 0.9500 . ? C13 C14 1.390(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C20 1.394(4) . ? C15 C16 1.406(4) . ? C16 C17 1.393(4) . ? C17 C18 1.387(4) . ? C17 H17 0.9500 . ? C18 C19 1.403(5) . ? C18 H18 0.9500 . ? C19 C20 1.384(5) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.418(4) . ? C22 C23 1.374(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? 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 N1 C3 114.3(3) . . ? C5 N2 C16 108.7(2) . . ? C5 N2 C6 127.7(2) . . ? C16 N2 C6 123.6(2) . . ? C5 N3 C21 113.0(3) . . ? C2 C1 C23 120.4(3) . . ? C2 C1 H1 119.8 . . ? C23 C1 H1 119.8 . . ? C1 C2 C3 120.1(3) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? N1 C3 C2 118.0(3) . . ? N1 C3 C21 122.2(3) . . ? C2 C3 C21 119.8(3) . . ? N1 C4 C5 122.8(3) . . ? N1 C4 C15 130.3(3) . . ? C5 C4 C15 106.9(2) . . ? N3 C5 N2 126.9(3) . . ? N3 C5 C4 125.0(3) . . ? N2 C5 C4 108.0(2) . . ? C14 C6 C7 120.4(3) . . ? C14 C6 N2 120.4(3) . . ? C7 C6 N2 119.1(3) . . ? C6 C7 C8 119.5(3) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C7 C8 C9 121.3(3) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C13 C9 C8 117.7(3) . . ? C13 C9 C10 121.5(3) . . ? C8 C9 C10 120.7(3) . . ? C12 C10 C11 116.0(3) . . ? C12 C10 C9 122.7(3) . . ? C11 C10 C9 121.2(3) . . ? C10 C11 C12 121.7(3) . 2_574 ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 2_574 . ? C10 C12 C11 122.3(3) . 2_574 ? C10 C12 H12 118.8 . . ? C11 C12 H12 118.8 2_574 . ? C14 C13 C9 121.1(3) . . ? C14 C13 H13 119.4 . . ? C9 C13 H13 119.4 . . ? C6 C14 C13 119.9(3) . . ? C6 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C20 C15 C16 120.3(3) . . ? C20 C15 C4 133.5(3) . . ? C16 C15 C4 106.2(3) . . ? C17 C16 N2 128.6(3) . . ? C17 C16 C15 121.2(3) . . ? N2 C16 C15 110.2(3) . . ? C18 C17 C16 117.7(3) . . ? C18 C17 H17 121.1 . . ? C16 C17 H17 121.1 . . ? C17 C18 C19 121.5(3) . . ? C17 C18 H18 119.2 . . ? C19 C18 H18 119.2 . . ? C20 C19 C18 120.5(3) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C15 118.7(3) . . ? C19 C20 H20 120.6 . . ? C15 C20 H20 120.6 . . ? N3 C21 C22 118.6(3) . . ? N3 C21 C3 122.7(3) . . ? C22 C21 C3 118.7(3) . . ? C23 C22 C21 120.3(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C1 120.7(3) . . ? C22 C23 H23 119.7 . . ? C1 C23 H23 119.7 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.53 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.648 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 932438' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_120509lt_0m #TrackingRef '19188_web_deposit_cif_file_2_Tsu-HuiSu_1365010386.BIQMCz.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C47 H29 N7' _chemical_formula_weight 691.77 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' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.8002(5) _cell_length_b 14.0687(6) _cell_length_c 19.6150(7) _cell_angle_alpha 80.878(3) _cell_angle_beta 85.943(2) _cell_angle_gamma 88.948(3) _cell_volume 3478.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2760 _cell_measurement_theta_min 2.7515 _cell_measurement_theta_max 21.2643 _exptl_crystal_description Columnar _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8411 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 39123 _diffrn_reflns_av_R_equivalents 0.0649 _diffrn_reflns_av_sigmaI/netI 0.1179 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.05 _diffrn_reflns_theta_max 26.39 _reflns_number_total 14116 _reflns_number_gt 6774 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0894P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14116 _refine_ls_number_parameters 975 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1666 _refine_ls_R_factor_gt 0.0715 _refine_ls_wR_factor_ref 0.2056 _refine_ls_wR_factor_gt 0.1561 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 N1 N 0.6107(2) 0.7200(2) 0.43881(16) 0.0423(8) Uani 1 1 d . . . N2 N 0.5755(2) 0.5777(2) 0.39043(14) 0.0354(7) Uani 1 1 d . . . N3 N 0.9541(2) 0.91906(19) 0.12045(14) 0.0352(7) Uani 1 1 d . . . N4 N 0.8013(2) 0.9030(2) 0.05902(16) 0.0449(8) Uani 1 1 d . . . N5 N 0.8383(2) 1.1044(2) 0.00657(17) 0.0499(9) Uani 1 1 d . . . N6 N 0.9658(2) 0.53878(18) 0.25063(13) 0.0300(6) Uani 1 1 d . . . N7 N 0.3991(2) 0.6918(2) 0.49979(15) 0.0409(8) Uani 1 1 d . . . N8 N 0.3013(2) 0.5996(2) 0.04842(17) 0.0459(8) Uani 1 1 d . . . N9 N 0.4535(2) 0.5474(2) 0.10884(16) 0.0400(8) Uani 1 1 d . . . N10 N 0.1280(2) 0.8417(2) 0.37245(14) 0.0409(8) Uani 1 1 d . . . N11 N 0.0984(2) 1.0096(2) 0.37869(15) 0.0439(8) Uani 1 1 d . . . N12 N 0.5316(2) 0.8506(2) 0.24718(15) 0.0429(8) Uani 1 1 d . . . N13 N -0.1063(2) 0.9440(2) 0.43789(14) 0.0361(7) Uani 1 1 d . . . N14 N 0.3083(2) 0.4053(2) 0.01590(17) 0.0479(8) Uani 1 1 d . . . C1 C 0.4820(5) 0.8893(5) 0.5801(4) 0.177(4) Uani 1 1 d . . . H1 H 0.4566 0.9260 0.6146 0.213 Uiso 1 1 calc R . . C2 C 0.4219(4) 0.8203(3) 0.5624(3) 0.0882(18) Uani 1 1 d . . . H2 H 0.3526 0.8106 0.5827 0.106 Uiso 1 1 calc R . . C3 C 0.4618(3) 0.7628(3) 0.5140(2) 0.0526(11) Uani 1 1 d . . . C4 C 0.5648(3) 0.7774(3) 0.4835(2) 0.0536(11) Uani 1 1 d . . . C5 C 0.5494(3) 0.6512(2) 0.42868(18) 0.0347(8) Uani 1 1 d . . . C6 C 0.6757(3) 0.5635(3) 0.35541(17) 0.0350(8) Uani 1 1 d . . . C7 C 0.7220(3) 0.6391(2) 0.31166(16) 0.0334(8) Uani 1 1 d . . . H7 H 0.6882 0.7002 0.3042 0.040 Uiso 1 1 calc R . . C8 C 0.8190(2) 0.6247(2) 0.27853(16) 0.0311(8) Uani 1 1 d . . . C9 C 0.8894(2) 0.6878(2) 0.23172(16) 0.0297(8) Uani 1 1 d . . . C10 C 0.8824(3) 0.7844(2) 0.20193(16) 0.0326(8) Uani 1 1 d . . . H10 H 0.8244 0.8232 0.2137 0.039 Uiso 1 1 calc R . . C11 C 0.9619(3) 0.8218(2) 0.15493(17) 0.0314(8) Uani 1 1 d . . . C12 C 0.8788(3) 0.9523(2) 0.07511(18) 0.0366(9) Uani 1 1 d . . . C13 C 0.7383(3) 0.9558(3) 0.0135(2) 0.0641(14) Uani 1 1 d . . . C14 C 0.6544(3) 0.9098(4) -0.0101(3) 0.109(2) Uani 1 1 d . . . H14 H 0.6428 0.8432 0.0054 0.131 Uiso 1 1 calc R . . C15 C 0.5904(4) 0.9601(5) -0.0547(4) 0.183(5) Uani 1 1 d . . . H15 H 0.5339 0.9282 -0.0701 0.220 Uiso 1 1 calc R . . C16 C 0.6057(4) 1.0592(5) -0.0790(4) 0.186(5) Uani 1 1 d . . . H16 H 0.5599 1.0932 -0.1104 0.224 Uiso 1 1 calc R . . C17 C 0.5833(5) 0.9064(5) 0.5467(4) 0.178(4) Uani 1 1 d . . . H17 H 0.6235 0.9577 0.5571 0.214 Uiso 1 1 calc R . . C18 C 0.6242(4) 0.8516(3) 0.5005(3) 0.096(2) Uani 1 1 d . . . H18 H 0.6929 0.8635 0.4797 0.116 Uiso 1 1 calc R . . C19 C 0.9773(2) 0.6325(2) 0.21519(16) 0.0274(8) Uani 1 1 d . . . C20 C 1.0580(2) 0.6707(2) 0.16753(16) 0.0288(8) Uani 1 1 d . . . H20 H 1.1173 0.6329 0.1566 0.035 Uiso 1 1 calc R . . C21 C 1.0483(2) 0.7656(2) 0.13703(17) 0.0306(8) Uani 1 1 d . . . H21 H 1.1008 0.7932 0.1035 0.037 Uiso 1 1 calc R . . C22 C 1.0237(3) 0.9939(2) 0.12254(18) 0.0416(9) Uani 1 1 d . . . C23 C 1.1101(4) 0.9923(3) 0.1617(2) 0.0615(13) Uani 1 1 d . . . H23 H 1.1296 0.9365 0.1922 0.074 Uiso 1 1 calc R . . C24 C 1.1663(5) 1.0772(3) 0.1533(3) 0.0900(19) Uani 1 1 d . . . H24 H 1.2256 1.0792 0.1796 0.108 Uiso 1 1 calc R . . C25 C 1.1403(4) 1.1594(3) 0.1085(2) 0.0797(16) Uani 1 1 d . . . H25 H 1.1824 1.2152 0.1040 0.096 Uiso 1 1 calc R . . C26 C 1.0535(3) 1.1603(3) 0.07055(19) 0.0513(11) Uani 1 1 d . . . H26 H 1.0349 1.2163 0.0399 0.062 Uiso 1 1 calc R . . C27 C 0.9936(3) 1.0768(2) 0.07816(18) 0.0412(9) Uani 1 1 d . . . C28 C 0.9000(3) 1.0525(2) 0.04842(19) 0.0390(9) Uani 1 1 d . . . C29 C 0.7554(3) 1.0559(3) -0.0115(3) 0.0702(15) Uani 1 1 d . . . C30 C 0.6859(3) 1.1054(4) -0.0574(3) 0.117(3) Uani 1 1 d . . . H30 H 0.6953 1.1723 -0.0734 0.141 Uiso 1 1 calc R . . C31 C 0.8686(2) 0.5333(2) 0.28899(16) 0.0303(8) Uani 1 1 d . . . C32 C 0.8211(3) 0.4570(2) 0.33356(17) 0.0333(8) Uani 1 1 d . . . H32 H 0.8537 0.3954 0.3409 0.040 Uiso 1 1 calc R . . C33 C 0.7249(3) 0.4734(2) 0.36701(17) 0.0332(8) Uani 1 1 d . . . H33 H 0.6919 0.4225 0.3983 0.040 Uiso 1 1 calc R . . C34 C 1.0444(2) 0.4656(2) 0.24946(16) 0.0295(8) Uani 1 1 d . . . C35 C 1.0197(3) 0.3735(2) 0.23993(17) 0.0329(8) Uani 1 1 d . . . H35 H 0.9491 0.3570 0.2355 0.039 Uiso 1 1 calc R . . C36 C 1.0994(3) 0.3053(2) 0.23696(17) 0.0366(9) Uani 1 1 d . . . H36 H 1.0817 0.2414 0.2325 0.044 Uiso 1 1 calc R . . C37 C 1.2038(3) 0.3275(2) 0.24032(17) 0.0353(8) Uani 1 1 d . . . C38 C 1.2263(3) 0.4207(3) 0.24994(17) 0.0377(9) Uani 1 1 d . . . H38 H 1.2970 0.4382 0.2526 0.045 Uiso 1 1 calc R . . C39 C 1.1475(3) 0.4882(2) 0.25573(17) 0.0339(8) Uani 1 1 d . . . H39 H 1.1645 0.5506 0.2641 0.041 Uiso 1 1 calc R . . C40 C 1.2902(3) 0.2536(3) 0.2356(2) 0.0518(11) Uani 1 1 d . . . H40A H 1.2710 0.1939 0.2666 0.078 Uiso 1 1 calc R . . H40B H 1.3554 0.2783 0.2492 0.078 Uiso 1 1 calc R . . H40C H 1.3002 0.2406 0.1879 0.078 Uiso 1 1 calc R . . C41 C 0.4881(3) 0.5178(3) 0.39462(17) 0.0378(9) Uani 1 1 d . . . C42 C 0.4779(3) 0.4346(3) 0.36563(18) 0.0445(10) Uani 1 1 d . . . H42 H 0.5336 0.4119 0.3377 0.053 Uiso 1 1 calc R . . C43 C 0.3834(3) 0.3858(3) 0.37899(19) 0.0518(11) Uani 1 1 d . . . H43 H 0.3749 0.3283 0.3603 0.062 Uiso 1 1 calc R . . C44 C 0.3007(3) 0.4194(3) 0.41932(19) 0.0505(11) Uani 1 1 d . . . H44 H 0.2371 0.3844 0.4279 0.061 Uiso 1 1 calc R . . C45 C 0.3104(3) 0.5030(3) 0.44687(18) 0.0439(10) Uani 1 1 d . . . H45 H 0.2535 0.5267 0.4733 0.053 Uiso 1 1 calc R . . C46 C 0.4056(3) 0.5521(3) 0.43519(17) 0.0362(9) Uani 1 1 d . . . C47 C 0.4430(3) 0.6363(2) 0.45789(18) 0.0346(8) Uani 1 1 d . . . C48 C 0.0865(4) 0.5071(4) -0.0780(3) 0.0807(16) Uani 1 1 d . . . H48 H 0.0363 0.4873 -0.1062 0.097 Uiso 1 1 calc R . . C49 C 0.1595(3) 0.4437(3) -0.0510(2) 0.0618(12) Uani 1 1 d . . . H49 H 0.1606 0.3797 -0.0610 0.074 Uiso 1 1 calc R . . C50 C 0.2341(3) 0.4717(3) -0.0081(2) 0.0495(10) Uani 1 1 d . . . C51 C 0.2312(3) 0.5672(3) 0.0069(2) 0.0496(10) Uani 1 1 d . . . C52 C 0.3714(3) 0.5349(2) 0.06919(19) 0.0395(9) Uani 1 1 d . . . C53 C 0.4743(3) 0.6302(2) 0.13952(18) 0.0372(9) Uani 1 1 d . . . C54 C 0.3988(3) 0.6637(2) 0.18356(17) 0.0338(8) Uani 1 1 d . . . H54 H 0.3317 0.6348 0.1915 0.041 Uiso 1 1 calc R . . C55 C 0.4227(2) 0.7406(2) 0.21615(17) 0.0328(8) Uani 1 1 d . . . C56 C 0.3661(2) 0.7901(3) 0.26588(17) 0.0364(9) Uani 1 1 d . . . C57 C 0.2626(3) 0.7872(3) 0.29322(17) 0.0381(9) Uani 1 1 d . . . H57 H 0.2134 0.7464 0.2785 0.046 Uiso 1 1 calc R . . C58 C 0.2326(3) 0.8450(3) 0.34234(18) 0.0463(10) Uani 1 1 d . . . C59 C 0.0681(3) 0.9198(3) 0.38788(17) 0.0387(9) Uani 1 1 d . . . C60 C 0.0237(3) 1.0711(3) 0.40139(18) 0.0421(10) Uani 1 1 d . . . C61 C 0.0474(3) 1.1691(3) 0.39652(19) 0.0497(11) Uani 1 1 d . . . H61 H 0.1143 1.1916 0.3772 0.060 Uiso 1 1 calc R . . C62 C -0.0239(4) 1.2326(3) 0.4191(2) 0.0542(12) Uani 1 1 d . . . H62 H -0.0058 1.2984 0.4157 0.065 Uiso 1 1 calc R . . C63 C -0.1243(3) 1.2014(3) 0.44724(19) 0.0492(10) Uani 1 1 d . . . H63 H -0.1740 1.2462 0.4619 0.059 Uiso 1 1 calc R . . C64 C 0.0850(4) 0.6027(3) -0.0640(3) 0.0838(17) Uani 1 1 d . . . H64 H 0.0348 0.6473 -0.0839 0.101 Uiso 1 1 calc R . . C65 C 0.1556(3) 0.6313(3) -0.0220(2) 0.0688(14) Uani 1 1 d . . . H65 H 0.1532 0.6955 -0.0125 0.083 Uiso 1 1 calc R . . C66 C 0.5240(2) 0.7809(2) 0.20473(17) 0.0336(8) Uani 1 1 d . . . C67 C 0.4353(3) 0.8560(3) 0.28510(18) 0.0452(10) Uani 1 1 d . . . C68 C 0.4059(3) 0.9143(3) 0.3336(2) 0.0620(13) Uani 1 1 d . . . H68 H 0.4539 0.9577 0.3467 0.074 Uiso 1 1 calc R . . C69 C 0.3045(3) 0.9073(3) 0.3626(2) 0.0657(14) Uani 1 1 d . . . H69 H 0.2828 0.9455 0.3969 0.079 Uiso 1 1 calc R . . C70 C 0.0667(3) 0.7575(3) 0.39215(17) 0.0377(9) Uani 1 1 d . . . C71 C -0.0345(3) 0.7836(3) 0.41644(17) 0.0353(9) Uani 1 1 d . . . C72 C -0.0344(3) 0.8861(3) 0.41579(17) 0.0343(8) Uani 1 1 d . . . C73 C -0.0770(3) 1.0385(3) 0.43108(17) 0.0380(9) Uani 1 1 d . . . C74 C -0.1496(3) 1.1059(3) 0.45335(18) 0.0422(9) Uani 1 1 d . . . H74 H -0.2169 1.0848 0.4728 0.051 Uiso 1 1 calc R . . C75 C -0.1091(3) 0.7124(3) 0.43851(18) 0.0398(9) Uani 1 1 d . . . H75 H -0.1779 0.7289 0.4542 0.048 Uiso 1 1 calc R . . C76 C -0.0807(3) 0.6174(3) 0.43712(19) 0.0425(9) Uani 1 1 d . . . H76 H -0.1311 0.5681 0.4513 0.051 Uiso 1 1 calc R . . C77 C 0.0207(3) 0.5929(3) 0.41512(18) 0.0429(9) Uani 1 1 d . . . H77 H 0.0388 0.5269 0.4161 0.051 Uiso 1 1 calc R . . C78 C 0.0960(3) 0.6624(3) 0.39181(18) 0.0399(9) Uani 1 1 d . . . H78 H 0.1648 0.6454 0.3762 0.048 Uiso 1 1 calc R . . C79 C 0.6146(2) 0.9180(2) 0.24535(17) 0.0323(8) Uani 1 1 d . . . C80 C 0.6424(3) 0.9800(3) 0.18512(18) 0.0399(9) Uani 1 1 d . . . H80 H 0.6081 0.9769 0.1442 0.048 Uiso 1 1 calc R . . C81 C 0.7208(3) 1.0470(2) 0.18484(19) 0.0384(9) Uani 1 1 d . . . H81 H 0.7406 1.0887 0.1431 0.046 Uiso 1 1 calc R . . C82 C 0.7709(3) 1.0543(2) 0.24415(19) 0.0356(9) Uani 1 1 d . . . C83 C 0.7413(3) 0.9911(2) 0.30368(18) 0.0372(9) Uani 1 1 d . . . H83 H 0.7742 0.9950 0.3450 0.045 Uiso 1 1 calc R . . C84 C 0.6650(2) 0.9225(2) 0.30454(18) 0.0357(9) Uani 1 1 d . . . H84 H 0.6475 0.8787 0.3457 0.043 Uiso 1 1 calc R . . C85 C 0.8554(3) 1.1282(3) 0.2446(2) 0.0552(11) Uani 1 1 d . . . H85A H 0.8438 1.1587 0.2861 0.083 Uiso 1 1 calc R . . H85B H 0.8530 1.1773 0.2033 0.083 Uiso 1 1 calc R . . H85C H 0.9242 1.0964 0.2447 0.083 Uiso 1 1 calc R . . C86 C 0.5992(3) 0.7490(3) 0.15886(18) 0.0362(9) Uani 1 1 d . . . H86 H 0.6663 0.7778 0.1502 0.043 Uiso 1 1 calc R . . C87 C 0.5723(3) 0.6738(2) 0.12648(18) 0.0374(9) Uani 1 1 d . . . H87 H 0.6219 0.6510 0.0944 0.045 Uiso 1 1 calc R . . C88 C 0.5105(3) 0.4610(3) 0.1206(2) 0.0477(10) Uani 1 1 d . . . C89 C 0.5961(3) 0.4389(3) 0.1597(3) 0.0697(14) Uani 1 1 d . . . H89 H 0.6255 0.4846 0.1836 0.084 Uiso 1 1 calc R . . C90 C 0.6363(4) 0.3469(4) 0.1622(4) 0.113(2) Uani 1 1 d . . . H90 H 0.6952 0.3290 0.1884 0.136 Uiso 1 1 calc R . . C91 C 0.5939(5) 0.2793(4) 0.1277(4) 0.134(3) Uani 1 1 d . . . H91 H 0.6244 0.2168 0.1311 0.161 Uiso 1 1 calc R . . C92 C 0.5092(4) 0.3009(3) 0.0890(3) 0.0937(18) Uani 1 1 d . . . H92 H 0.4810 0.2546 0.0652 0.112 Uiso 1 1 calc R . . C93 C 0.4659(3) 0.3923(3) 0.0857(2) 0.0534(11) Uani 1 1 d . . . C94 C 0.3764(3) 0.4387(2) 0.0530(2) 0.0421(9) 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 0.0364(18) 0.0308(17) 0.054(2) 0.0020(15) 0.0147(15) 0.0031(14) N2 0.0254(16) 0.0494(19) 0.0277(17) 0.0016(14) 0.0048(13) 0.0040(13) N3 0.0442(18) 0.0277(16) 0.0305(17) 0.0022(13) 0.0026(14) 0.0052(13) N4 0.0256(17) 0.0471(19) 0.051(2) 0.0200(16) 0.0075(15) 0.0033(14) N5 0.0363(19) 0.049(2) 0.052(2) 0.0203(17) 0.0193(16) 0.0135(16) N6 0.0315(16) 0.0282(15) 0.0272(16) 0.0010(12) 0.0058(13) 0.0048(12) N7 0.0371(18) 0.0364(17) 0.043(2) 0.0073(15) 0.0117(15) 0.0084(14) N8 0.0455(19) 0.0399(18) 0.057(2) -0.0212(16) -0.0105(16) 0.0099(15) N9 0.0314(17) 0.0339(17) 0.054(2) -0.0047(15) -0.0003(15) 0.0069(13) N10 0.0312(17) 0.061(2) 0.0318(18) -0.0158(15) 0.0109(13) -0.0125(15) N11 0.044(2) 0.059(2) 0.0287(18) -0.0064(16) 0.0012(15) -0.0184(17) N12 0.0253(17) 0.071(2) 0.0348(18) -0.0158(16) 0.0040(13) -0.0147(15) N13 0.0397(18) 0.0432(18) 0.0253(16) -0.0054(14) 0.0000(13) -0.0071(15) N14 0.047(2) 0.0348(18) 0.062(2) -0.0156(16) 0.0134(17) -0.0044(16) C1 0.120(5) 0.130(5) 0.303(10) -0.166(7) 0.154(6) -0.083(4) C2 0.061(3) 0.060(3) 0.146(5) -0.053(3) 0.064(3) -0.017(2) C3 0.042(2) 0.032(2) 0.078(3) -0.005(2) 0.027(2) -0.0011(18) C4 0.048(3) 0.030(2) 0.076(3) -0.008(2) 0.035(2) -0.0019(18) C5 0.030(2) 0.037(2) 0.031(2) 0.0069(16) 0.0076(16) 0.0087(16) C6 0.029(2) 0.048(2) 0.0244(19) 0.0013(17) 0.0052(15) 0.0039(17) C7 0.034(2) 0.040(2) 0.0237(19) 0.0000(16) 0.0037(16) 0.0102(16) C8 0.032(2) 0.0344(19) 0.0240(19) 0.0014(15) 0.0041(15) 0.0051(15) C9 0.0307(19) 0.0322(19) 0.0244(19) -0.0024(15) 0.0040(15) 0.0055(15) C10 0.036(2) 0.035(2) 0.0254(19) -0.0044(15) 0.0038(16) 0.0073(15) C11 0.037(2) 0.0295(19) 0.0251(19) 0.0009(15) 0.0037(16) 0.0029(15) C12 0.038(2) 0.032(2) 0.034(2) 0.0057(16) 0.0159(17) 0.0083(17) C13 0.025(2) 0.071(3) 0.078(3) 0.041(3) 0.001(2) 0.002(2) C14 0.042(3) 0.104(4) 0.149(5) 0.092(4) -0.039(3) -0.035(3) C15 0.077(4) 0.151(6) 0.274(9) 0.162(6) -0.103(5) -0.068(4) C16 0.054(3) 0.163(6) 0.287(10) 0.175(7) -0.086(5) -0.059(4) C17 0.125(6) 0.129(5) 0.302(10) -0.166(7) 0.153(6) -0.088(4) C18 0.074(3) 0.067(3) 0.152(5) -0.059(3) 0.076(3) -0.035(3) C19 0.0312(19) 0.0267(18) 0.0229(18) 0.0002(14) -0.0007(15) 0.0031(14) C20 0.0318(19) 0.0276(18) 0.0267(19) -0.0061(15) 0.0026(15) 0.0037(14) C21 0.0309(19) 0.0298(19) 0.030(2) -0.0035(15) 0.0049(15) -0.0002(15) C22 0.067(3) 0.028(2) 0.030(2) -0.0087(16) -0.0002(19) 0.0018(18) C23 0.106(4) 0.035(2) 0.048(3) -0.0076(19) -0.030(3) -0.007(2) C24 0.159(5) 0.039(3) 0.079(4) -0.003(2) -0.064(4) -0.024(3) C25 0.147(5) 0.034(2) 0.063(3) -0.008(2) -0.039(3) -0.019(3) C26 0.097(3) 0.025(2) 0.033(2) -0.0072(17) 0.001(2) 0.001(2) C27 0.068(3) 0.027(2) 0.027(2) -0.0047(16) 0.0089(19) 0.0085(18) C28 0.037(2) 0.037(2) 0.036(2) 0.0056(17) 0.0187(18) 0.0115(17) C29 0.025(2) 0.068(3) 0.094(4) 0.051(3) 0.010(2) 0.002(2) C30 0.030(3) 0.104(4) 0.178(6) 0.105(4) -0.018(3) -0.009(3) C31 0.0285(19) 0.035(2) 0.0243(19) 0.0019(15) 0.0026(15) 0.0042(15) C32 0.035(2) 0.0322(19) 0.030(2) 0.0011(16) 0.0006(16) 0.0041(15) C33 0.034(2) 0.039(2) 0.0238(19) 0.0001(16) 0.0045(16) -0.0008(16) C34 0.031(2) 0.0322(19) 0.0224(18) 0.0010(15) 0.0016(15) 0.0050(15) C35 0.032(2) 0.032(2) 0.032(2) 0.0001(15) 0.0035(16) -0.0003(16) C36 0.044(2) 0.035(2) 0.031(2) -0.0075(16) 0.0043(17) 0.0055(17) C37 0.040(2) 0.039(2) 0.029(2) -0.0099(16) -0.0083(16) 0.0100(17) C38 0.037(2) 0.046(2) 0.033(2) -0.0134(17) -0.0078(17) 0.0096(17) C39 0.038(2) 0.034(2) 0.030(2) -0.0069(16) -0.0032(16) 0.0062(16) C40 0.048(2) 0.056(3) 0.058(3) -0.028(2) -0.014(2) 0.018(2) C41 0.032(2) 0.053(2) 0.026(2) 0.0013(17) -0.0015(16) 0.0004(18) C42 0.037(2) 0.066(3) 0.032(2) -0.0106(19) 0.0000(17) -0.0010(19) C43 0.042(2) 0.082(3) 0.032(2) -0.015(2) 0.0022(19) -0.008(2) C44 0.035(2) 0.081(3) 0.038(2) -0.014(2) -0.0020(18) -0.011(2) C45 0.032(2) 0.066(3) 0.031(2) -0.0007(19) -0.0007(17) 0.0016(19) C46 0.029(2) 0.053(2) 0.0237(19) 0.0033(17) 0.0021(16) 0.0037(17) C47 0.028(2) 0.038(2) 0.033(2) 0.0042(17) 0.0063(16) 0.0074(16) C48 0.080(4) 0.081(4) 0.100(4) -0.062(3) -0.033(3) 0.013(3) C49 0.067(3) 0.054(3) 0.075(3) -0.045(2) -0.005(3) 0.003(2) C50 0.049(3) 0.043(2) 0.060(3) -0.025(2) 0.007(2) 0.004(2) C51 0.056(3) 0.039(2) 0.061(3) -0.025(2) -0.013(2) 0.0086(19) C52 0.040(2) 0.032(2) 0.046(2) -0.0081(17) 0.0055(18) 0.0037(17) C53 0.035(2) 0.037(2) 0.038(2) -0.0022(17) 0.0007(17) 0.0011(16) C54 0.0279(19) 0.043(2) 0.028(2) 0.0035(16) 0.0021(16) -0.0021(16) C55 0.0265(19) 0.044(2) 0.027(2) -0.0012(16) -0.0007(15) -0.0027(16) C56 0.0245(19) 0.063(2) 0.0230(19) -0.0111(17) 0.0017(15) -0.0121(17) C57 0.028(2) 0.063(3) 0.024(2) -0.0088(18) 0.0028(15) -0.0129(17) C58 0.027(2) 0.085(3) 0.029(2) -0.016(2) 0.0073(16) -0.0136(19) C59 0.039(2) 0.053(2) 0.024(2) -0.0075(18) -0.0008(16) -0.0138(19) C60 0.049(2) 0.055(3) 0.022(2) 0.0009(18) -0.0113(18) -0.016(2) C61 0.060(3) 0.051(3) 0.036(2) 0.009(2) -0.015(2) -0.020(2) C62 0.079(3) 0.043(2) 0.041(3) 0.004(2) -0.029(2) -0.013(2) C63 0.066(3) 0.047(2) 0.035(2) -0.0022(18) -0.019(2) -0.004(2) C64 0.097(4) 0.077(3) 0.097(4) -0.057(3) -0.055(3) 0.036(3) C65 0.078(3) 0.065(3) 0.079(3) -0.047(3) -0.040(3) 0.030(3) C66 0.0263(19) 0.049(2) 0.026(2) -0.0032(17) -0.0042(15) -0.0022(16) C67 0.028(2) 0.080(3) 0.029(2) -0.017(2) 0.0042(16) -0.0145(19) C68 0.035(2) 0.114(4) 0.048(3) -0.049(3) 0.0124(19) -0.029(2) C69 0.041(2) 0.120(4) 0.046(3) -0.050(3) 0.0164(19) -0.033(2) C70 0.028(2) 0.060(3) 0.026(2) -0.0127(18) 0.0002(16) -0.0067(18) C71 0.030(2) 0.053(2) 0.025(2) -0.0109(17) 0.0026(15) -0.0065(17) C72 0.032(2) 0.050(2) 0.0210(19) -0.0066(16) -0.0004(15) -0.0056(17) C73 0.047(2) 0.044(2) 0.024(2) -0.0036(17) -0.0064(17) -0.0107(18) C74 0.054(3) 0.043(2) 0.030(2) -0.0040(17) -0.0094(18) -0.0078(19) C75 0.033(2) 0.052(2) 0.035(2) -0.0108(18) 0.0058(16) -0.0044(18) C76 0.036(2) 0.050(2) 0.042(2) -0.0122(19) 0.0081(17) -0.0068(18) C77 0.039(2) 0.053(2) 0.038(2) -0.0132(19) 0.0055(18) 0.0012(18) C78 0.030(2) 0.056(3) 0.034(2) -0.0122(19) 0.0029(16) -0.0006(18) C79 0.0191(17) 0.045(2) 0.032(2) -0.0062(17) 0.0002(15) -0.0039(15) C80 0.029(2) 0.057(2) 0.032(2) -0.0008(18) -0.0018(16) 0.0056(18) C81 0.033(2) 0.041(2) 0.036(2) 0.0046(17) 0.0086(17) 0.0100(17) C82 0.0277(19) 0.035(2) 0.043(2) -0.0081(17) 0.0071(17) 0.0004(15) C83 0.033(2) 0.043(2) 0.037(2) -0.0093(18) -0.0037(16) -0.0044(16) C84 0.0297(19) 0.045(2) 0.031(2) -0.0031(17) -0.0005(16) -0.0028(16) C85 0.054(3) 0.050(3) 0.060(3) -0.015(2) 0.019(2) -0.017(2) C86 0.0229(19) 0.046(2) 0.036(2) 0.0007(18) 0.0019(16) -0.0011(16) C87 0.029(2) 0.043(2) 0.037(2) -0.0019(17) 0.0042(16) 0.0070(16) C88 0.037(2) 0.040(2) 0.059(3) 0.007(2) 0.008(2) 0.0094(18) C89 0.049(3) 0.054(3) 0.101(4) 0.003(3) -0.009(3) 0.019(2) C90 0.083(4) 0.079(4) 0.176(7) -0.007(4) -0.043(4) 0.039(3) C91 0.117(6) 0.050(4) 0.238(9) -0.022(5) -0.057(6) 0.046(4) C92 0.087(4) 0.042(3) 0.153(6) -0.018(3) -0.014(4) 0.022(3) C93 0.049(3) 0.032(2) 0.075(3) -0.004(2) 0.013(2) 0.0054(19) C94 0.040(2) 0.030(2) 0.053(3) -0.0068(18) 0.0177(19) 0.0027(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 N1 C5 1.304(4) . ? N1 C4 1.379(5) . ? N2 C5 1.393(4) . ? N2 C41 1.403(4) . ? N2 C6 1.437(4) . ? N3 C12 1.383(4) . ? N3 C22 1.399(4) . ? N3 C11 1.432(4) . ? N4 C12 1.305(4) . ? N4 C13 1.367(5) . ? N5 C28 1.308(4) . ? N5 C29 1.369(5) . ? N6 C19 1.394(4) . ? N6 C31 1.405(4) . ? N6 C34 1.428(4) . ? N7 C47 1.312(4) . ? N7 C3 1.367(5) . ? N8 C52 1.305(4) . ? N8 C51 1.383(4) . ? N9 C52 1.381(4) . ? N9 C88 1.401(4) . ? N9 C53 1.431(4) . ? N10 C59 1.388(5) . ? N10 C70 1.419(4) . ? N10 C58 1.423(4) . ? N11 C59 1.311(4) . ? N11 C60 1.376(5) . ? N12 C66 1.392(4) . ? N12 C67 1.401(4) . ? N12 C79 1.431(4) . ? N13 C72 1.314(4) . ? N13 C73 1.372(4) . ? N14 C94 1.313(5) . ? N14 C50 1.374(5) . ? C1 C2 1.352(6) . ? C1 C17 1.416(7) . ? C1 H1 0.9500 . ? C2 C3 1.406(6) . ? C2 H2 0.9500 . ? C3 C4 1.412(5) . ? C4 C18 1.398(6) . ? C5 C47 1.446(4) . ? C6 C7 1.372(4) . ? C6 C33 1.398(5) . ? C7 C8 1.388(4) . ? C7 H7 0.9500 . ? C8 C31 1.416(4) . ? C8 C9 1.448(4) . ? C9 C10 1.396(4) . ? C9 C19 1.404(4) . ? C10 C11 1.377(4) . ? C10 H10 0.9500 . ? C11 C21 1.405(4) . ? C12 C28 1.447(4) . ? C13 C14 1.406(6) . ? C13 C29 1.431(5) . ? C14 C15 1.350(6) . ? C14 H14 0.9500 . ? C15 C16 1.412(7) . ? C15 H15 0.9500 . ? C16 C30 1.352(7) . ? C16 H16 0.9500 . ? C17 C18 1.352(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.399(4) . ? C20 C21 1.380(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.388(5) . ? C22 C27 1.406(5) . ? C23 C24 1.388(5) . ? C23 H23 0.9500 . ? C24 C25 1.387(6) . ? C24 H24 0.9500 . ? C25 C26 1.379(6) . ? C25 H25 0.9500 . ? C26 C27 1.396(5) . ? C26 H26 0.9500 . ? C27 C28 1.439(5) . ? C29 C30 1.406(6) . ? C30 H30 0.9500 . ? C31 C32 1.392(4) . ? C32 C33 1.387(4) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 C39 1.382(4) . ? C34 C35 1.383(4) . ? C35 C36 1.393(4) . ? C35 H35 0.9500 . ? C36 C37 1.386(4) . ? C36 H36 0.9500 . ? C37 C38 1.391(4) . ? C37 C40 1.513(5) . ? C38 C39 1.383(5) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 C42 1.392(5) . ? C41 C46 1.402(5) . ? C42 C43 1.389(5) . ? C42 H42 0.9500 . ? C43 C44 1.397(5) . ? C43 H43 0.9500 . ? C44 C45 1.381(5) . ? C44 H44 0.9500 . ? C45 C46 1.398(5) . ? C45 H45 0.9500 . ? C46 C47 1.432(5) . ? C48 C49 1.356(6) . ? C48 C64 1.414(6) . ? C48 H48 0.9500 . ? C49 C50 1.418(5) . ? C49 H49 0.9500 . ? C50 C51 1.419(5) . ? C51 C65 1.398(5) . ? C52 C94 1.437(5) . ? C53 C54 1.377(5) . ? C53 C87 1.397(4) . ? C54 C55 1.390(5) . ? C54 H54 0.9500 . ? C55 C66 1.414(4) . ? C55 C56 1.434(5) . ? C56 C57 1.392(4) . ? C56 C67 1.406(4) . ? C57 C58 1.386(5) . ? C57 H57 0.9500 . ? C58 C69 1.401(5) . ? C59 C72 1.444(5) . ? C60 C61 1.404(5) . ? C60 C73 1.429(5) . ? C61 C62 1.366(6) . ? C61 H61 0.9500 . ? C62 C63 1.412(5) . ? C62 H62 0.9500 . ? C63 C74 1.372(5) . ? C63 H63 0.9500 . ? C64 C65 1.372(5) . ? C64 H64 0.9500 . ? C65 H65 0.9500 . ? C66 C86 1.388(5) . ? C67 C68 1.380(5) . ? C68 C69 1.379(5) . ? C68 H68 0.9500 . ? C69 H69 0.9500 . ? C70 C78 1.384(5) . ? C70 C71 1.411(5) . ? C71 C75 1.393(4) . ? C71 C72 1.441(5) . ? C73 C74 1.412(5) . ? C74 H74 0.9500 . ? C75 C76 1.383(5) . ? C75 H75 0.9500 . ? C76 C77 1.394(5) . ? C76 H76 0.9500 . ? C77 C78 1.386(5) . ? C77 H77 0.9500 . ? C78 H78 0.9500 . ? C79 C84 1.378(4) . ? C79 C80 1.382(5) . ? C80 C81 1.388(5) . ? C80 H80 0.9500 . ? C81 C82 1.386(5) . ? C81 H81 0.9500 . ? C82 C83 1.385(5) . ? C82 C85 1.516(4) . ? C83 C84 1.383(4) . ? C83 H83 0.9500 . ? C84 H84 0.9500 . ? C85 H85A 0.9800 . ? C85 H85B 0.9800 . ? C85 H85C 0.9800 . ? C86 C87 1.377(5) . ? C86 H86 0.9500 . ? C87 H87 0.9500 . ? C88 C89 1.385(5) . ? C88 C93 1.418(5) . ? C89 C90 1.380(6) . ? C89 H89 0.9500 . ? C90 C91 1.389(8) . ? C90 H90 0.9500 . ? C91 C92 1.370(7) . ? C91 H91 0.9500 . ? C92 C93 1.384(6) . ? C92 H92 0.9500 . ? C93 C94 1.447(5) . ? 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 C5 N1 C4 112.8(3) . . ? C5 N2 C41 107.9(3) . . ? C5 N2 C6 126.0(3) . . ? C41 N2 C6 126.1(3) . . ? C12 N3 C22 108.7(3) . . ? C12 N3 C11 124.5(3) . . ? C22 N3 C11 126.7(3) . . ? C12 N4 C13 113.2(3) . . ? C28 N5 C29 115.0(3) . . ? C19 N6 C31 107.9(3) . . ? C19 N6 C34 124.0(3) . . ? C31 N6 C34 128.0(3) . . ? C47 N7 C3 115.0(3) . . ? C52 N8 C51 113.0(3) . . ? C52 N9 C88 108.9(3) . . ? C52 N9 C53 127.2(3) . . ? C88 N9 C53 123.7(3) . . ? C59 N10 C70 108.0(3) . . ? C59 N10 C58 126.3(3) . . ? C70 N10 C58 125.7(3) . . ? C59 N11 C60 113.4(3) . . ? C66 N12 C67 108.2(3) . . ? C66 N12 C79 127.2(3) . . ? C67 N12 C79 123.7(3) . . ? C72 N13 C73 114.8(3) . . ? C94 N14 C50 113.9(3) . . ? C2 C1 C17 119.3(5) . . ? C2 C1 H1 120.3 . . ? C17 C1 H1 120.3 . . ? C1 C2 C3 120.1(4) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? N7 C3 C2 117.7(3) . . ? N7 C3 C4 122.3(4) . . ? C2 C3 C4 119.9(4) . . ? N1 C4 C18 118.2(3) . . ? N1 C4 C3 122.8(3) . . ? C18 C4 C3 119.0(4) . . ? N1 C5 N2 126.5(3) . . ? N1 C5 C47 125.3(3) . . ? N2 C5 C47 108.1(3) . . ? C7 C6 C33 121.1(3) . . ? C7 C6 N2 119.3(3) . . ? C33 C6 N2 119.6(3) . . ? C6 C7 C8 118.7(3) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? C7 C8 C31 120.6(3) . . ? C7 C8 C9 132.9(3) . . ? C31 C8 C9 106.5(3) . . ? C10 C9 C19 120.1(3) . . ? C10 C9 C8 132.8(3) . . ? C19 C9 C8 107.1(3) . . ? C11 C10 C9 118.0(3) . . ? C11 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? C10 C11 C21 121.7(3) . . ? C10 C11 N3 119.4(3) . . ? C21 C11 N3 118.8(3) . . ? N4 C12 N3 126.5(3) . . ? N4 C12 C28 125.4(3) . . ? N3 C12 C28 108.1(3) . . ? N4 C13 C14 118.7(4) . . ? N4 C13 C29 122.4(4) . . ? C14 C13 C29 118.9(4) . . ? C15 C14 C13 120.2(4) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 121.4(5) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C30 C16 C15 119.9(5) . . ? C30 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C18 C17 C1 121.7(5) . . ? C18 C17 H17 119.1 . . ? C1 C17 H17 119.1 . . ? C17 C18 C4 119.7(4) . . ? C17 C18 H18 120.1 . . ? C4 C18 H18 120.1 . . ? N6 C19 C20 128.8(3) . . ? N6 C19 C9 109.4(3) . . ? C20 C19 C9 121.7(3) . . ? C21 C20 C19 117.4(3) . . ? C21 C20 H20 121.3 . . ? C19 C20 H20 121.3 . . ? C20 C21 C11 121.0(3) . . ? C20 C21 H21 119.5 . . ? C11 C21 H21 119.5 . . ? C23 C22 N3 127.9(3) . . ? C23 C22 C27 122.2(3) . . ? N3 C22 C27 109.8(3) . . ? C24 C23 C22 115.8(4) . . ? C24 C23 H23 122.1 . . ? C22 C23 H23 122.1 . . ? C25 C24 C23 123.3(4) . . ? C25 C24 H24 118.4 . . ? C23 C24 H24 118.4 . . ? C26 C25 C24 120.3(4) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C27 118.4(4) . . ? C25 C26 H26 120.8 . . ? C27 C26 H26 120.8 . . ? C26 C27 C22 120.0(4) . . ? C26 C27 C28 133.5(3) . . ? C22 C27 C28 106.5(3) . . ? N5 C28 C27 131.3(3) . . ? N5 C28 C12 121.8(3) . . ? C27 C28 C12 106.9(3) . . ? N5 C29 C30 119.0(4) . . ? N5 C29 C13 122.1(4) . . ? C30 C29 C13 118.8(4) . . ? C16 C30 C29 120.9(5) . . ? C16 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C32 C31 N6 130.7(3) . . ? C32 C31 C8 120.2(3) . . ? N6 C31 C8 109.0(3) . . ? C33 C32 C31 118.3(3) . . ? C33 C32 H32 120.9 . . ? C31 C32 H32 120.9 . . ? C32 C33 C6 121.1(3) . . ? C32 C33 H33 119.5 . . ? C6 C33 H33 119.5 . . ? C39 C34 C35 119.5(3) . . ? C39 C34 N6 119.2(3) . . ? C35 C34 N6 121.2(3) . . ? C34 C35 C36 119.2(3) . . ? C34 C35 H35 120.4 . . ? C36 C35 H35 120.4 . . ? C37 C36 C35 122.2(3) . . ? C37 C36 H36 118.9 . . ? C35 C36 H36 118.9 . . ? C36 C37 C38 117.2(3) . . ? C36 C37 C40 121.9(3) . . ? C38 C37 C40 120.8(3) . . ? C39 C38 C37 121.2(3) . . ? C39 C38 H38 119.4 . . ? C37 C38 H38 119.4 . . ? C34 C39 C38 120.5(3) . . ? C34 C39 H39 119.7 . . ? C38 C39 H39 119.7 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C42 C41 C46 121.3(3) . . ? C42 C41 N2 128.5(3) . . ? C46 C41 N2 110.2(3) . . ? C43 C42 C41 117.7(4) . . ? C43 C42 H42 121.1 . . ? C41 C42 H42 121.1 . . ? C42 C43 C44 121.4(4) . . ? C42 C43 H43 119.3 . . ? C44 C43 H43 119.3 . . ? C45 C44 C43 120.7(4) . . ? C45 C44 H44 119.7 . . ? C43 C44 H44 119.7 . . ? C44 C45 C46 118.7(4) . . ? C44 C45 H45 120.6 . . ? C46 C45 H45 120.6 . . ? C45 C46 C41 120.1(3) . . ? C45 C46 C47 133.1(3) . . ? C41 C46 C47 106.7(3) . . ? N7 C47 C46 131.1(3) . . ? N7 C47 C5 121.7(3) . . ? C46 C47 C5 107.1(3) . . ? C49 C48 C64 120.0(4) . . ? C49 C48 H48 120.0 . . ? C64 C48 H48 120.0 . . ? C48 C49 C50 120.7(4) . . ? C48 C49 H49 119.6 . . ? C50 C49 H49 119.6 . . ? N14 C50 C49 118.1(4) . . ? N14 C50 C51 122.7(4) . . ? C49 C50 C51 119.2(4) . . ? N8 C51 C65 118.7(3) . . ? N8 C51 C50 122.4(4) . . ? C65 C51 C50 118.9(3) . . ? N8 C52 N9 126.2(3) . . ? N8 C52 C94 125.0(3) . . ? N9 C52 C94 108.7(3) . . ? C54 C53 C87 120.8(3) . . ? C54 C53 N9 119.6(3) . . ? C87 C53 N9 119.5(3) . . ? C53 C54 C55 118.8(3) . . ? C53 C54 H54 120.6 . . ? C55 C54 H54 120.6 . . ? C54 C55 C66 119.5(3) . . ? C54 C55 C56 133.4(3) . . ? C66 C55 C56 106.9(3) . . ? C57 C56 C67 119.3(3) . . ? C57 C56 C55 133.4(3) . . ? C67 C56 C55 107.2(3) . . ? C58 C57 C56 118.9(3) . . ? C58 C57 H57 120.6 . . ? C56 C57 H57 120.6 . . ? C57 C58 C69 120.5(3) . . ? C57 C58 N10 120.1(3) . . ? C69 C58 N10 119.4(3) . . ? N11 C59 N10 126.2(3) . . ? N11 C59 C72 125.0(4) . . ? N10 C59 C72 108.8(3) . . ? N11 C60 C61 119.1(4) . . ? N11 C60 C73 122.3(3) . . ? C61 C60 C73 118.6(4) . . ? C62 C61 C60 121.2(4) . . ? C62 C61 H61 119.4 . . ? C60 C61 H61 119.4 . . ? C61 C62 C63 120.7(4) . . ? C61 C62 H62 119.7 . . ? C63 C62 H62 119.7 . . ? C74 C63 C62 119.6(4) . . ? C74 C63 H63 120.2 . . ? C62 C63 H63 120.2 . . ? C65 C64 C48 120.4(4) . . ? C65 C64 H64 119.8 . . ? C48 C64 H64 119.8 . . ? C64 C65 C51 120.8(4) . . ? C64 C65 H65 119.6 . . ? C51 C65 H65 119.6 . . ? C86 C66 N12 129.4(3) . . ? C86 C66 C55 121.7(3) . . ? N12 C66 C55 108.8(3) . . ? C68 C67 N12 129.2(3) . . ? C68 C67 C56 122.1(3) . . ? N12 C67 C56 108.8(3) . . ? C69 C68 C67 117.8(3) . . ? C69 C68 H68 121.1 . . ? C67 C68 H68 121.1 . . ? C68 C69 C58 121.3(4) . . ? C68 C69 H69 119.3 . . ? C58 C69 H69 119.3 . . ? C78 C70 C71 122.0(3) . . ? C78 C70 N10 128.8(3) . . ? C71 C70 N10 109.2(3) . . ? C75 C71 C70 119.6(3) . . ? C75 C71 C72 133.2(3) . . ? C70 C71 C72 107.1(3) . . ? N13 C72 C71 131.0(3) . . ? N13 C72 C59 122.2(3) . . ? C71 C72 C59 106.7(3) . . ? N13 C73 C74 118.7(3) . . ? N13 C73 C60 122.3(4) . . ? C74 C73 C60 119.1(3) . . ? C63 C74 C73 120.9(4) . . ? C63 C74 H74 119.5 . . ? C73 C74 H74 119.5 . . ? C76 C75 C71 118.6(3) . . ? C76 C75 H75 120.7 . . ? C71 C75 H75 120.7 . . ? C75 C76 C77 120.8(3) . . ? C75 C76 H76 119.6 . . ? C77 C76 H76 119.6 . . ? C78 C77 C76 121.7(4) . . ? C78 C77 H77 119.1 . . ? C76 C77 H77 119.1 . . ? C70 C78 C77 117.2(3) . . ? C70 C78 H78 121.4 . . ? C77 C78 H78 121.4 . . ? C84 C79 C80 120.0(3) . . ? C84 C79 N12 119.7(3) . . ? C80 C79 N12 120.3(3) . . ? C79 C80 C81 119.6(3) . . ? C79 C80 H80 120.2 . . ? C81 C80 H80 120.2 . . ? C82 C81 C80 121.4(3) . . ? C82 C81 H81 119.3 . . ? C80 C81 H81 119.3 . . ? C83 C82 C81 117.6(3) . . ? C83 C82 C85 120.6(3) . . ? C81 C82 C85 121.8(3) . . ? C84 C83 C82 121.8(3) . . ? C84 C83 H83 119.1 . . ? C82 C83 H83 119.1 . . ? C79 C84 C83 119.6(3) . . ? C79 C84 H84 120.2 . . ? C83 C84 H84 120.2 . . ? C82 C85 H85A 109.5 . . ? C82 C85 H85B 109.5 . . ? H85A C85 H85B 109.5 . . ? C82 C85 H85C 109.5 . . ? H85A C85 H85C 109.5 . . ? H85B C85 H85C 109.5 . . ? C87 C86 C66 117.2(3) . . ? C87 C86 H86 121.4 . . ? C66 C86 H86 121.4 . . ? C86 C87 C53 121.8(3) . . ? C86 C87 H87 119.1 . . ? C53 C87 H87 119.1 . . ? C89 C88 N9 129.0(4) . . ? C89 C88 C93 121.8(4) . . ? N9 C88 C93 109.2(3) . . ? C90 C89 C88 116.3(5) . . ? C90 C89 H89 121.9 . . ? C88 C89 H89 121.9 . . ? C89 C90 C91 122.4(5) . . ? C89 C90 H90 118.8 . . ? C91 C90 H90 118.8 . . ? C92 C91 C90 121.4(5) . . ? C92 C91 H91 119.3 . . ? C90 C91 H91 119.3 . . ? C91 C92 C93 118.0(5) . . ? C91 C92 H92 121.0 . . ? C93 C92 H92 121.0 . . ? C92 C93 C88 120.1(4) . . ? C92 C93 C94 133.4(4) . . ? C88 C93 C94 106.5(3) . . ? N14 C94 C52 123.0(4) . . ? N14 C94 C93 130.3(3) . . ? C52 C94 C93 106.7(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.570 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 932439'