# Electronic Supplementary Material (ESI) for RSC Advances # 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_a12892 _database_code_depnum_ccdc_archive 'CCDC 876488' #TrackingRef '10759_web_deposit_cif_file_0_Chien-TienChen_1334635330.a12892_3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H26 N2' _chemical_formula_sum 'C40 H26 N2' _chemical_formula_weight 534.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.4103(6) _cell_length_b 10.5880(4) _cell_length_c 16.0074(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.814(2) _cell_angle_gamma 90.00 _cell_volume 2771.51(18) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9525 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17458 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4866 _reflns_number_gt 3680 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0684P)^2^+0.4832P] 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 4866 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _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 0.90888(10) 0.69213(18) -0.02575(9) 0.0326(4) Uani 1 1 d . . . C2 C 0.89454(9) 0.55890(15) -0.02234(9) 0.0300(4) Uani 1 1 d . . . C3 C 0.91103(10) 0.48087(16) -0.08890(10) 0.0343(4) Uani 1 1 d . . . H3 H 0.9328 0.5141 -0.1375 0.041 Uiso 1 1 calc R . . C4 C 0.89481(10) 0.35525(17) -0.08194(10) 0.0358(4) Uani 1 1 d . . . H4 H 0.9054 0.3015 -0.1273 0.043 Uiso 1 1 calc R . . C5 C 0.86316(9) 0.30042(16) -0.01092(9) 0.0309(4) Uani 1 1 d . . . C6 C 0.84412(9) 0.38009(15) 0.05522(9) 0.0256(4) Uani 1 1 d . . . C7 C 0.86106(9) 0.50835(15) 0.04724(9) 0.0282(4) Uani 1 1 d . . . H7 H 0.8492 0.5637 0.0913 0.034 Uiso 1 1 calc R . . C8 C 0.85686(11) 0.16422(17) -0.01306(10) 0.0420(5) Uani 1 1 d . . . H8 H 0.8813 0.1262 -0.0586 0.050 Uiso 1 1 calc R . . C9 C 0.82318(11) 0.08226(16) 0.03695(10) 0.0396(4) Uani 1 1 d . . . H9 H 0.8291 -0.0036 0.0213 0.048 Uiso 1 1 calc R . . C10 C 0.77929(9) 0.10014(15) 0.11060(9) 0.0296(4) Uani 1 1 d . . . C11 C 0.77056(9) 0.21381(14) 0.15474(9) 0.0263(4) Uani 1 1 d . . . C12 C 0.81707(9) 0.33953(14) 0.14199(9) 0.0255(4) Uani 1 1 d . . . C13 C 0.72430(9) 0.21023(15) 0.22441(9) 0.0298(4) Uani 1 1 d . . . H13 H 0.7188 0.2859 0.2553 0.036 Uiso 1 1 calc R . . C14 C 0.68593(9) 0.10186(15) 0.25087(10) 0.0309(4) Uani 1 1 d . . . C15 C 0.69528(10) -0.00957(16) 0.20678(10) 0.0346(4) Uani 1 1 d . . . H15 H 0.6702 -0.0854 0.2232 0.041 Uiso 1 1 calc R . . C16 C 0.74119(10) -0.00825(16) 0.13936(10) 0.0350(4) Uani 1 1 d . . . H16 H 0.7477 -0.0853 0.1102 0.042 Uiso 1 1 calc R . . C17 C 0.60699(10) 0.22291(15) 0.34720(10) 0.0328(4) Uani 1 1 d . . . C18 C 0.55401(11) 0.29339(17) 0.29377(11) 0.0431(5) Uani 1 1 d . . . H18 H 0.5381 0.2634 0.2389 0.052 Uiso 1 1 calc R . . C19 C 0.52436(11) 0.40705(19) 0.32035(13) 0.0520(5) Uani 1 1 d . . . H19 H 0.4886 0.4557 0.2833 0.062 Uiso 1 1 calc R . . C20 C 0.54597(12) 0.4504(2) 0.39965(14) 0.0545(5) Uani 1 1 d . . . H20 H 0.5249 0.5285 0.4177 0.065 Uiso 1 1 calc R . . C21 C 0.59827(12) 0.3808(2) 0.45322(13) 0.0538(5) Uani 1 1 d . . . H21 H 0.6131 0.4107 0.5084 0.065 Uiso 1 1 calc R . . C22 C 0.62925(11) 0.26762(17) 0.42698(11) 0.0415(4) Uani 1 1 d . . . H22 H 0.6660 0.2204 0.4639 0.050 Uiso 1 1 calc R . . C23 C 0.63025(10) -0.00237(16) 0.37206(10) 0.0330(4) Uani 1 1 d . . . C24 C 0.55448(11) -0.0331(2) 0.39789(12) 0.0532(5) Uani 1 1 d . . . H24 H 0.5083 0.0174 0.3804 0.064 Uiso 1 1 calc R . . C25 C 0.54517(13) -0.1364(2) 0.44900(13) 0.0578(6) Uani 1 1 d . . . H25 H 0.4926 -0.1565 0.4660 0.069 Uiso 1 1 calc R . . C26 C 0.61069(13) -0.20991(18) 0.47524(11) 0.0469(5) Uani 1 1 d . . . H26 H 0.6041 -0.2809 0.5103 0.056 Uiso 1 1 calc R . . C27 C 0.68625(12) -0.17972(18) 0.45017(11) 0.0460(5) Uani 1 1 d . . . H27 H 0.7324 -0.2299 0.4684 0.055 Uiso 1 1 calc R . . C28 C 0.69581(11) -0.07681(17) 0.39858(10) 0.0393(4) Uani 1 1 d . . . H28 H 0.7484 -0.0575 0.3813 0.047 Uiso 1 1 calc R . . C29 C 0.76959(9) 0.44777(14) 0.17808(9) 0.0260(4) Uani 1 1 d . . . C30 C 0.69411(10) 0.49577(15) 0.14852(10) 0.0329(4) Uani 1 1 d . . . H30 H 0.6657 0.4626 0.0992 0.039 Uiso 1 1 calc R . . C31 C 0.66093(10) 0.59332(16) 0.19254(11) 0.0390(4) Uani 1 1 d . . . H31 H 0.6095 0.6281 0.1727 0.047 Uiso 1 1 calc R . . C32 C 0.70167(11) 0.64035(17) 0.26465(11) 0.0411(4) Uani 1 1 d . . . H32 H 0.6769 0.7050 0.2950 0.049 Uiso 1 1 calc R . . C33 C 0.77790(11) 0.59517(16) 0.29375(10) 0.0361(4) Uani 1 1 d . . . H33 H 0.8060 0.6289 0.3431 0.043 Uiso 1 1 calc R . . C34 C 0.81236(9) 0.49910(15) 0.24897(9) 0.0271(4) Uani 1 1 d . . . C35 C 0.89207(9) 0.43432(14) 0.26250(9) 0.0265(4) Uani 1 1 d . . . C36 C 0.89505(9) 0.33950(14) 0.20235(9) 0.0245(3) Uani 1 1 d . . . C37 C 0.96305(10) 0.26376(15) 0.20003(10) 0.0320(4) Uani 1 1 d . . . H37 H 0.9646 0.1987 0.1593 0.038 Uiso 1 1 calc R . . C38 C 1.02927(10) 0.28437(17) 0.25831(10) 0.0371(4) Uani 1 1 d . . . H38 H 1.0765 0.2327 0.2577 0.044 Uiso 1 1 calc R . . C39 C 1.02692(10) 0.37984(17) 0.31729(10) 0.0380(4) Uani 1 1 d . . . H39 H 1.0730 0.3938 0.3563 0.046 Uiso 1 1 calc R . . C40 C 0.95825(10) 0.45510(16) 0.32007(10) 0.0328(4) Uani 1 1 d . . . H40 H 0.9566 0.5200 0.3609 0.039 Uiso 1 1 calc R . . N1 N 0.91824(10) 0.79947(16) -0.02934(9) 0.0464(4) Uani 1 1 d . . . N2 N 0.63877(8) 0.10571(13) 0.32015(9) 0.0379(4) 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 0.0374(10) 0.0385(11) 0.0225(9) 0.0068(8) 0.0066(7) 0.0018(8) C2 0.0305(9) 0.0341(10) 0.0251(9) 0.0052(7) 0.0011(7) 0.0016(7) C3 0.0384(9) 0.0424(11) 0.0231(8) 0.0061(8) 0.0076(7) 0.0030(8) C4 0.0435(10) 0.0412(11) 0.0241(9) -0.0040(8) 0.0107(7) 0.0025(8) C5 0.0353(9) 0.0340(10) 0.0241(8) -0.0026(7) 0.0060(7) 0.0028(7) C6 0.0253(8) 0.0305(9) 0.0207(8) 0.0014(7) 0.0008(6) 0.0019(7) C7 0.0328(9) 0.0324(10) 0.0193(8) 0.0007(7) 0.0022(6) 0.0016(7) C8 0.0616(12) 0.0349(11) 0.0324(10) -0.0097(8) 0.0210(9) 0.0012(9) C9 0.0556(11) 0.0309(10) 0.0341(10) -0.0082(8) 0.0146(8) 0.0017(8) C10 0.0332(9) 0.0299(9) 0.0259(9) -0.0042(7) 0.0037(7) 0.0006(7) C11 0.0289(8) 0.0286(9) 0.0209(8) 0.0001(7) 0.0001(6) -0.0002(7) C12 0.0308(8) 0.0260(9) 0.0200(8) -0.0009(7) 0.0037(6) -0.0004(7) C13 0.0356(9) 0.0274(9) 0.0270(8) -0.0037(7) 0.0057(7) -0.0007(7) C14 0.0328(9) 0.0332(10) 0.0272(9) 0.0009(7) 0.0060(7) -0.0006(7) C15 0.0419(10) 0.0283(9) 0.0342(9) 0.0013(8) 0.0075(7) -0.0050(8) C16 0.0448(10) 0.0287(9) 0.0317(9) -0.0050(7) 0.0048(7) -0.0028(8) C17 0.0332(9) 0.0330(10) 0.0340(9) 0.0035(8) 0.0136(7) -0.0020(8) C18 0.0411(10) 0.0513(12) 0.0371(10) 0.0026(9) 0.0045(8) 0.0048(9) C19 0.0426(11) 0.0520(13) 0.0624(14) 0.0105(11) 0.0107(9) 0.0147(10) C20 0.0538(13) 0.0467(13) 0.0655(14) -0.0106(11) 0.0205(11) 0.0071(10) C21 0.0592(13) 0.0552(14) 0.0476(12) -0.0158(10) 0.0086(10) -0.0015(11) C22 0.0425(10) 0.0451(12) 0.0370(10) 0.0016(9) 0.0043(8) 0.0005(9) C23 0.0395(10) 0.0324(10) 0.0282(9) 0.0016(7) 0.0079(7) -0.0049(8) C24 0.0390(11) 0.0612(14) 0.0614(13) 0.0213(11) 0.0155(9) 0.0025(10) C25 0.0495(12) 0.0638(14) 0.0628(14) 0.0189(12) 0.0217(10) -0.0117(11) C26 0.0693(14) 0.0369(11) 0.0348(10) 0.0038(8) 0.0059(9) -0.0100(10) C27 0.0538(12) 0.0447(12) 0.0386(10) 0.0047(9) -0.0017(9) 0.0019(9) C28 0.0365(10) 0.0455(11) 0.0357(10) 0.0039(8) 0.0018(8) -0.0049(8) C29 0.0305(8) 0.0247(9) 0.0235(8) 0.0028(7) 0.0071(6) 0.0001(7) C30 0.0364(9) 0.0334(10) 0.0292(9) -0.0001(7) 0.0049(7) 0.0006(8) C31 0.0372(10) 0.0361(10) 0.0446(11) -0.0001(8) 0.0090(8) 0.0074(8) C32 0.0507(11) 0.0302(10) 0.0445(11) -0.0044(8) 0.0162(9) 0.0066(9) C33 0.0463(10) 0.0321(10) 0.0309(9) -0.0057(7) 0.0092(8) -0.0029(8) C34 0.0350(9) 0.0239(8) 0.0235(8) 0.0011(7) 0.0090(7) -0.0034(7) C35 0.0362(9) 0.0251(9) 0.0188(8) 0.0025(7) 0.0065(6) -0.0039(7) C36 0.0290(8) 0.0261(8) 0.0189(8) 0.0024(6) 0.0054(6) -0.0019(7) C37 0.0359(9) 0.0340(10) 0.0266(9) 0.0025(7) 0.0052(7) 0.0022(8) C38 0.0341(10) 0.0432(11) 0.0342(10) 0.0070(8) 0.0047(7) 0.0048(8) C39 0.0347(10) 0.0480(11) 0.0306(9) 0.0079(8) -0.0016(7) -0.0086(8) C40 0.0403(10) 0.0325(10) 0.0257(9) 0.0005(7) 0.0036(7) -0.0088(8) N1 0.0601(10) 0.0419(10) 0.0385(9) 0.0075(7) 0.0116(7) 0.0015(8) N2 0.0468(9) 0.0315(8) 0.0380(8) 0.0048(6) 0.0191(7) 0.0010(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.149(2) . ? C1 C2 1.432(2) . ? C2 C7 1.390(2) . ? C2 C3 1.393(2) . ? C3 C4 1.363(2) . ? C3 H3 0.9500 . ? C4 C5 1.414(2) . ? C4 H4 0.9500 . ? C5 C6 1.409(2) . ? C5 C8 1.446(2) . ? C6 C7 1.394(2) . ? C6 C12 1.5538(19) . ? C7 H7 0.9500 . ? C8 C9 1.332(2) . ? C8 H8 0.9500 . ? C9 C10 1.445(2) . ? C9 H9 0.9500 . ? C10 C16 1.403(2) . ? C10 C11 1.409(2) . ? C11 C13 1.401(2) . ? C11 C12 1.556(2) . ? C12 C29 1.526(2) . ? C12 C36 1.537(2) . ? C13 C14 1.392(2) . ? C13 H13 0.9500 . ? C14 C15 1.390(2) . ? C14 N2 1.4051(19) . ? C15 C16 1.367(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.382(2) . ? C17 C18 1.385(2) . ? C17 N2 1.427(2) . ? C18 C19 1.379(3) . ? C18 H18 0.9500 . ? C19 C20 1.368(3) . ? C19 H19 0.9500 . ? C20 C21 1.375(3) . ? C20 H20 0.9500 . ? C21 C22 1.381(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C28 1.372(2) . ? C23 C24 1.382(2) . ? C23 N2 1.428(2) . ? C24 C25 1.382(3) . ? C24 H24 0.9500 . ? C25 C26 1.365(3) . ? C25 H25 0.9500 . ? C26 C27 1.373(3) . ? C26 H26 0.9500 . ? C27 C28 1.384(2) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.385(2) . ? C29 C34 1.394(2) . ? C30 C31 1.387(2) . ? C30 H30 0.9500 . ? C31 C32 1.378(2) . ? C31 H31 0.9500 . ? C32 C33 1.383(2) . ? C32 H32 0.9500 . ? C33 C34 1.392(2) . ? C33 H33 0.9500 . ? C34 C35 1.477(2) . ? C35 C40 1.382(2) . ? C35 C36 1.395(2) . ? C36 C37 1.377(2) . ? C37 C38 1.389(2) . ? C37 H37 0.9500 . ? C38 C39 1.386(2) . ? C38 H38 0.9500 . ? C39 C40 1.384(2) . ? C39 H39 0.9500 . ? C40 H40 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 N1 C1 C2 178.16(18) . . ? C7 C2 C3 120.00(15) . . ? C7 C2 C1 119.16(15) . . ? C3 C2 C1 120.80(14) . . ? C4 C3 C2 117.69(14) . . ? C4 C3 H3 121.2 . . ? C2 C3 H3 121.2 . . ? C3 C4 C5 123.64(15) . . ? C3 C4 H4 118.2 . . ? C5 C4 H4 118.2 . . ? C6 C5 C4 118.56(15) . . ? C6 C5 C8 126.51(14) . . ? C4 C5 C8 114.89(14) . . ? C7 C6 C5 117.12(14) . . ? C7 C6 C12 115.17(13) . . ? C5 C6 C12 127.17(14) . . ? C2 C7 C6 122.94(15) . . ? C2 C7 H7 118.5 . . ? C6 C7 H7 118.5 . . ? C9 C8 C5 131.92(15) . . ? C9 C8 H8 114.0 . . ? C5 C8 H8 114.0 . . ? C8 C9 C10 131.73(16) . . ? C8 C9 H9 114.1 . . ? C10 C9 H9 114.1 . . ? C16 C10 C11 117.86(14) . . ? C16 C10 C9 115.28(14) . . ? C11 C10 C9 126.86(14) . . ? C13 C11 C10 117.43(14) . . ? C13 C11 C12 115.59(13) . . ? C10 C11 C12 126.38(13) . . ? C29 C12 C36 100.76(11) . . ? C29 C12 C6 108.90(12) . . ? C36 C12 C6 106.06(11) . . ? C29 C12 C11 108.73(11) . . ? C36 C12 C11 108.00(11) . . ? C6 C12 C11 122.25(12) . . ? C14 C13 C11 123.62(14) . . ? C14 C13 H13 118.2 . . ? C11 C13 H13 118.2 . . ? C13 C14 C15 118.25(14) . . ? C13 C14 N2 120.63(14) . . ? C15 C14 N2 121.12(14) . . ? C16 C15 C14 118.93(15) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C10 123.90(15) . . ? C15 C16 H16 118.1 . . ? C10 C16 H16 118.1 . . ? C22 C17 C18 119.30(16) . . ? C22 C17 N2 120.20(15) . . ? C18 C17 N2 120.49(15) . . ? C19 C18 C17 119.94(18) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 120.57(19) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 119.88(19) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C20 C21 C22 120.12(19) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C17 C22 C21 120.18(17) . . ? C17 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C28 C23 C24 118.32(16) . . ? C28 C23 N2 121.85(14) . . ? C24 C23 N2 119.82(16) . . ? C23 C24 C25 120.68(18) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C26 C25 C24 120.68(18) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C27 119.01(18) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? C26 C27 C28 120.54(18) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C23 C28 C27 120.77(16) . . ? C23 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C30 C29 C34 120.66(14) . . ? C30 C29 C12 128.07(14) . . ? C34 C29 C12 111.27(13) . . ? C31 C30 C29 118.54(15) . . ? C31 C30 H30 120.7 . . ? C29 C30 H30 120.7 . . ? C32 C31 C30 120.74(16) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C31 C32 C33 121.26(16) . . ? C31 C32 H32 119.4 . . ? C33 C32 H32 119.4 . . ? C32 C33 C34 118.32(16) . . ? C32 C33 H33 120.8 . . ? C34 C33 H33 120.8 . . ? C29 C34 C33 120.39(15) . . ? C29 C34 C35 108.52(13) . . ? C33 C34 C35 131.09(14) . . ? C40 C35 C36 120.25(14) . . ? C40 C35 C34 131.36(14) . . ? C36 C35 C34 108.37(13) . . ? C37 C36 C35 120.88(14) . . ? C37 C36 C12 128.08(13) . . ? C35 C36 C12 110.98(13) . . ? C36 C37 C38 118.71(15) . . ? C36 C37 H37 120.6 . . ? C38 C37 H37 120.6 . . ? C37 C38 C39 120.48(16) . . ? C37 C38 H38 119.8 . . ? C39 C38 H38 119.8 . . ? C40 C39 C38 120.74(15) . . ? C40 C39 H39 119.6 . . ? C38 C39 H39 119.6 . . ? C35 C40 C39 118.91(15) . . ? C35 C40 H40 120.5 . . ? C39 C40 H40 120.5 . . ? C14 N2 C17 120.27(13) . . ? C14 N2 C23 121.56(13) . . ? C17 N2 C23 117.64(12) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.205 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.041 data_11466 _database_code_depnum_ccdc_archive 'CCDC 876489' #TrackingRef '10760_web_deposit_cif_file_1_Chien-TienChen_1334635330.11466_3b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H30 N2' _chemical_formula_sum 'C46 H30 N2' _chemical_formula_weight 610.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.6125(6) _cell_length_b 8.5624(2) _cell_length_c 26.3251(6) _cell_angle_alpha 90.00 _cell_angle_beta 116.5440(10) _cell_angle_gamma 90.00 _cell_volume 6777.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 15012 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour yellow-green _exptl_crystal_size_max 0.74 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2560 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8938 _exptl_absorpt_correction_T_max 1.0649 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12504 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5645 _reflns_number_gt 4240 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.2000P)^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 5645 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.2167 _refine_ls_wR_factor_gt 0.1961 _refine_ls_goodness_of_fit_ref 0.860 _refine_ls_restrained_S_all 0.860 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.00025(9) -0.4321(3) 0.92842(13) 0.0505(7) Uani 1 1 d . . . C2 C 0.97490(8) -0.2921(3) 0.91059(11) 0.0397(6) Uani 1 1 d . . . C3 C 0.96843(9) -0.1987(3) 0.94973(11) 0.0451(7) Uani 1 1 d . . . H3 H 0.9790 -0.2325 0.9879 0.054 Uiso 1 1 calc R . . C4 C 0.94674(9) -0.0576(3) 0.93309(11) 0.0418(6) Uani 1 1 d . . . H4 H 0.9421 0.0035 0.9601 0.050 Uiso 1 1 calc R . . C5 C 0.93140(7) -0.0017(3) 0.87752(9) 0.0312(5) Uani 1 1 d . . . C6 C 0.93776(8) -0.0970(3) 0.83877(11) 0.0416(6) Uani 1 1 d . . . H6 H 0.9272 -0.0630 0.8006 0.050 Uiso 1 1 calc R . . C7 C 0.95919(9) -0.2403(3) 0.85465(12) 0.0450(6) Uani 1 1 d . . . H7 H 0.9632 -0.3030 0.8275 0.054 Uiso 1 1 calc R . . C8 C 0.90822(7) 0.1510(3) 0.86045(9) 0.0307(5) Uani 1 1 d . . . C9 C 0.91282(8) 0.2686(3) 0.89949(10) 0.0368(6) Uani 1 1 d . . . H9 H 0.9315 0.2527 0.9388 0.044 Uiso 1 1 calc R . . C10 C 0.89040(8) 0.4070(3) 0.88111(10) 0.0348(6) Uani 1 1 d . . . H10 H 0.8942 0.4855 0.9084 0.042 Uiso 1 1 calc R . . C11 C 0.86179(7) 0.4380(2) 0.82324(10) 0.0303(5) Uani 1 1 d . . . C12 C 0.85720(7) 0.3206(2) 0.78298(9) 0.0272(5) Uani 1 1 d . . . C13 C 0.88052(7) 0.1818(2) 0.80353(9) 0.0283(5) Uani 1 1 d . . . H13 H 0.8773 0.1024 0.7767 0.034 Uiso 1 1 calc R . . C14 C 0.83298(7) 0.3435(2) 0.71763(9) 0.0264(5) Uani 1 1 d . . . C15 C 0.83105(7) 0.1877(2) 0.68827(9) 0.0272(5) Uani 1 1 d . . . C16 C 0.80860(8) 0.0517(2) 0.68920(10) 0.0333(5) Uani 1 1 d . . . H16 H 0.7915 0.0481 0.7098 0.040 Uiso 1 1 calc R . . C17 C 0.81156(9) -0.0783(3) 0.65961(11) 0.0415(6) Uani 1 1 d . . . H17 H 0.7969 -0.1723 0.6606 0.050 Uiso 1 1 calc R . . C18 C 0.83569(9) -0.0723(3) 0.62863(11) 0.0443(7) Uani 1 1 d . . . H18 H 0.8368 -0.1615 0.6079 0.053 Uiso 1 1 calc R . . C19 C 0.85818(9) 0.0620(3) 0.62750(11) 0.0412(6) Uani 1 1 d . . . H19 H 0.8750 0.0652 0.6065 0.049 Uiso 1 1 calc R . . C20 C 0.85578(7) 0.1930(3) 0.65776(9) 0.0313(5) Uani 1 1 d . . . C21 C 0.87635(7) 0.3465(3) 0.66513(9) 0.0320(5) Uani 1 1 d . . . C22 C 0.90474(9) 0.4063(3) 0.64434(11) 0.0431(6) Uani 1 1 d . . . H22 H 0.9126 0.3451 0.6201 0.052 Uiso 1 1 calc R . . C23 C 0.92123(9) 0.5555(3) 0.65940(12) 0.0448(7) Uani 1 1 d . . . H23 H 0.9409 0.5968 0.6457 0.054 Uiso 1 1 calc R . . C24 C 0.90944(9) 0.6462(3) 0.69434(11) 0.0438(6) Uani 1 1 d . . . H24 H 0.9213 0.7483 0.7048 0.053 Uiso 1 1 calc R . . C25 C 0.88027(8) 0.5879(3) 0.71408(10) 0.0348(5) Uani 1 1 d . . . H25 H 0.8717 0.6508 0.7373 0.042 Uiso 1 1 calc R . . C26 C 0.86391(7) 0.4393(2) 0.69987(9) 0.0278(5) Uani 1 1 d . . . C27 C 0.78536(7) 0.4156(2) 0.69262(9) 0.0251(5) Uani 1 1 d . . . C28 C 0.77248(8) 0.5425(2) 0.71604(9) 0.0289(5) Uani 1 1 d . . . C29 C 0.80104(8) 0.6288(3) 0.76731(10) 0.0331(5) Uani 1 1 d . . . H29 H 0.7909 0.7307 0.7698 0.040 Uiso 1 1 calc R . . C30 C 0.83932(8) 0.5872(3) 0.81153(10) 0.0346(5) Uani 1 1 d . . . H30 H 0.8536 0.6666 0.8389 0.042 Uiso 1 1 calc R . . C31 C 0.72844(8) 0.5935(3) 0.68684(10) 0.0354(6) Uani 1 1 d . . . H31 H 0.7195 0.6791 0.7023 0.042 Uiso 1 1 calc R . . C32 C 0.69729(8) 0.5283(3) 0.63741(10) 0.0365(6) Uani 1 1 d . . . H32 H 0.6674 0.5640 0.6206 0.044 Uiso 1 1 calc R . . C33 C 0.71046(7) 0.4086(3) 0.61230(10) 0.0306(5) Uani 1 1 d . . . C34 C 0.75433(7) 0.3561(2) 0.64051(9) 0.0274(5) Uani 1 1 d . . . H34 H 0.7636 0.2756 0.6233 0.033 Uiso 1 1 calc R . . C35 C 0.64286(7) 0.4151(3) 0.51940(10) 0.0318(5) Uani 1 1 d . . . C36 C 0.64343(9) 0.5732(3) 0.50818(11) 0.0418(6) Uani 1 1 d . . . H36 H 0.6696 0.6324 0.5292 0.050 Uiso 1 1 calc R . . C37 C 0.60646(10) 0.6457(3) 0.46689(11) 0.0497(7) Uani 1 1 d . . . H37 H 0.6069 0.7548 0.4606 0.060 Uiso 1 1 calc R . . C38 C 0.56880(9) 0.5596(3) 0.43472(11) 0.0504(7) Uani 1 1 d . . . H38 H 0.5435 0.6088 0.4057 0.060 Uiso 1 1 calc R . . C39 C 0.56793(8) 0.4023(3) 0.44480(10) 0.0417(6) Uani 1 1 d . . . H39 H 0.5420 0.3431 0.4226 0.050 Uiso 1 1 calc R . . C40 C 0.60460(8) 0.3295(3) 0.48710(10) 0.0355(6) Uani 1 1 d . . . H40 H 0.6036 0.2211 0.4941 0.043 Uiso 1 1 calc R . . C41 C 0.69209(7) 0.1908(3) 0.54407(10) 0.0320(5) Uani 1 1 d . . . C42 C 0.69700(9) 0.1809(3) 0.49476(11) 0.0429(6) Uani 1 1 d . . . H42 H 0.6942 0.2717 0.4727 0.051 Uiso 1 1 calc R . . C43 C 0.70604(10) 0.0383(3) 0.47788(13) 0.0521(7) Uani 1 1 d . . . H43 H 0.7091 0.0311 0.4438 0.062 Uiso 1 1 calc R . . C44 C 0.71067(10) -0.0940(3) 0.51006(13) 0.0519(7) Uani 1 1 d . . . H44 H 0.7163 -0.1924 0.4979 0.062 Uiso 1 1 calc R . . C45 C 0.70701(10) -0.0821(3) 0.56027(12) 0.0504(7) Uani 1 1 d . . . H45 H 0.7111 -0.1720 0.5833 0.060 Uiso 1 1 calc R . . C46 C 0.69743(9) 0.0600(3) 0.57697(11) 0.0399(6) Uani 1 1 d . . . H46 H 0.6945 0.0677 0.6112 0.048 Uiso 1 1 calc R . . N1 N 1.02168(10) -0.5425(3) 0.94322(14) 0.0752(9) Uani 1 1 d . . . N2 N 0.68115(6) 0.3386(2) 0.56082(9) 0.0366(5) 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 0.0446(16) 0.0513(16) 0.0577(19) 0.0181(13) 0.0248(14) 0.0076(12) C2 0.0297(12) 0.0390(14) 0.0455(16) 0.0127(11) 0.0125(11) 0.0006(10) C3 0.0428(15) 0.0536(16) 0.0374(15) 0.0204(12) 0.0166(12) 0.0099(12) C4 0.0429(14) 0.0487(15) 0.0347(15) 0.0121(11) 0.0183(12) 0.0035(11) C5 0.0235(11) 0.0394(13) 0.0267(13) 0.0064(9) 0.0075(10) -0.0022(9) C6 0.0391(14) 0.0494(15) 0.0270(13) 0.0073(11) 0.0065(11) 0.0076(11) C7 0.0395(14) 0.0454(15) 0.0417(16) 0.0032(11) 0.0107(12) 0.0043(11) C8 0.0260(11) 0.0364(13) 0.0277(13) 0.0033(9) 0.0102(10) -0.0016(9) C9 0.0331(12) 0.0498(15) 0.0216(12) 0.0016(10) 0.0070(10) -0.0018(10) C10 0.0378(13) 0.0412(13) 0.0229(12) -0.0054(9) 0.0115(11) -0.0043(10) C11 0.0287(12) 0.0373(13) 0.0250(12) -0.0014(9) 0.0120(10) -0.0024(9) C12 0.0238(11) 0.0330(12) 0.0244(12) 0.0007(9) 0.0105(9) -0.0014(8) C13 0.0273(11) 0.0331(12) 0.0230(12) 0.0014(9) 0.0099(9) -0.0019(9) C14 0.0257(11) 0.0308(12) 0.0229(12) 0.0015(8) 0.0111(10) 0.0020(8) C15 0.0275(11) 0.0281(11) 0.0200(11) 0.0020(8) 0.0054(9) 0.0076(8) C16 0.0355(12) 0.0310(12) 0.0300(13) 0.0034(9) 0.0116(10) 0.0044(9) C17 0.0479(15) 0.0290(13) 0.0374(15) 0.0010(10) 0.0097(12) 0.0048(10) C18 0.0586(17) 0.0349(14) 0.0320(14) -0.0049(10) 0.0135(13) 0.0135(12) C19 0.0485(15) 0.0437(15) 0.0340(14) -0.0025(10) 0.0208(12) 0.0114(11) C20 0.0327(12) 0.0346(12) 0.0241(12) 0.0009(9) 0.0104(10) 0.0092(9) C21 0.0272(11) 0.0455(14) 0.0231(12) 0.0049(9) 0.0109(10) 0.0083(9) C22 0.0421(15) 0.0567(16) 0.0379(15) 0.0062(12) 0.0244(13) 0.0063(12) C23 0.0419(14) 0.0567(17) 0.0446(16) 0.0072(12) 0.0271(13) -0.0018(12) C24 0.0416(14) 0.0449(15) 0.0474(16) 0.0082(11) 0.0222(13) -0.0030(11) C25 0.0367(13) 0.0363(13) 0.0327(14) 0.0032(10) 0.0167(11) 0.0029(10) C26 0.0233(11) 0.0361(12) 0.0210(11) 0.0076(9) 0.0072(9) 0.0048(9) C27 0.0251(11) 0.0282(11) 0.0221(11) 0.0038(8) 0.0105(9) 0.0040(8) C28 0.0333(12) 0.0292(12) 0.0260(12) 0.0019(9) 0.0149(10) 0.0030(9) C29 0.0405(13) 0.0310(12) 0.0296(13) -0.0011(9) 0.0174(11) 0.0052(10) C30 0.0404(14) 0.0346(12) 0.0279(13) -0.0042(9) 0.0143(11) -0.0009(10) C31 0.0363(13) 0.0391(13) 0.0340(14) -0.0021(10) 0.0187(11) 0.0074(10) C32 0.0286(12) 0.0446(14) 0.0357(14) 0.0006(11) 0.0137(11) 0.0088(10) C33 0.0272(11) 0.0342(12) 0.0280(13) 0.0017(9) 0.0103(10) 0.0029(9) C34 0.0315(12) 0.0272(11) 0.0254(12) 0.0016(9) 0.0145(10) 0.0021(9) C35 0.0248(12) 0.0385(13) 0.0269(13) -0.0054(9) 0.0069(10) 0.0019(9) C36 0.0441(15) 0.0385(14) 0.0346(15) -0.0028(11) 0.0102(12) 0.0017(11) C37 0.0626(19) 0.0408(15) 0.0353(15) 0.0009(11) 0.0125(14) 0.0186(13) C38 0.0438(15) 0.072(2) 0.0288(14) -0.0015(13) 0.0102(12) 0.0270(14) C39 0.0239(12) 0.0678(18) 0.0291(14) -0.0095(11) 0.0080(11) 0.0046(11) C40 0.0301(12) 0.0456(14) 0.0308(13) -0.0048(10) 0.0134(11) 0.0004(10) C41 0.0252(11) 0.0331(12) 0.0318(13) -0.0024(9) 0.0076(10) 0.0009(9) C42 0.0451(15) 0.0471(15) 0.0380(15) 0.0075(11) 0.0199(13) 0.0079(11) C43 0.0542(17) 0.0627(19) 0.0466(17) -0.0053(13) 0.0291(15) 0.0112(13) C44 0.0545(17) 0.0408(16) 0.0515(18) -0.0104(12) 0.0156(14) 0.0086(12) C45 0.0581(18) 0.0342(14) 0.0442(17) -0.0018(11) 0.0097(14) -0.0080(12) C46 0.0449(15) 0.0388(14) 0.0310(14) -0.0059(10) 0.0125(12) -0.0108(11) N1 0.0740(19) 0.0715(19) 0.085(2) 0.0410(16) 0.0398(18) 0.0336(15) N2 0.0283(11) 0.0369(11) 0.0351(12) -0.0028(8) 0.0056(9) 0.0046(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.146(3) . ? C1 C2 1.424(4) . ? C2 C3 1.396(4) . ? C2 C7 1.396(4) . ? C3 C4 1.378(3) . ? C3 H3 0.9500 . ? C4 C5 1.400(3) . ? C4 H4 0.9500 . ? C5 C6 1.395(3) . ? C5 C8 1.485(3) . ? C6 C7 1.389(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.391(3) . ? C8 C9 1.398(3) . ? C9 C10 1.371(3) . ? C9 H9 0.9500 . ? C10 C11 1.417(3) . ? C10 H10 0.9500 . ? C11 C12 1.418(3) . ? C11 C30 1.446(3) . ? C12 C13 1.393(3) . ? C12 C14 1.552(3) . ? C13 H13 0.9500 . ? C14 C15 1.529(3) . ? C14 C26 1.552(3) . ? C14 C27 1.560(3) . ? C15 C20 1.391(3) . ? C15 C16 1.393(3) . ? C16 C17 1.388(3) . ? C16 H16 0.9500 . ? C17 C18 1.384(4) . ? C17 H17 0.9500 . ? C18 C19 1.383(4) . ? C18 H18 0.9500 . ? C19 C20 1.399(3) . ? C19 H19 0.9500 . ? C20 C21 1.457(3) . ? C21 C22 1.392(3) . ? C21 C26 1.409(3) . ? C22 C23 1.378(4) . ? C22 H22 0.9500 . ? C23 C24 1.390(4) . ? C23 H23 0.9500 . ? C24 C25 1.392(3) . ? C24 H24 0.9500 . ? C25 C26 1.370(3) . ? C25 H25 0.9500 . ? C27 C28 1.409(3) . ? C27 C34 1.397(3) . ? C28 C31 1.399(3) . ? C28 C29 1.460(3) . ? C29 C30 1.341(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C32 1.372(3) . ? C31 H31 0.9500 . ? C32 C33 1.395(3) . ? C32 H32 0.9500 . ? C33 C34 1.396(3) . ? C33 N2 1.405(3) . ? C34 H34 0.9500 . ? C35 C40 1.392(3) . ? C35 C36 1.387(3) . ? C35 N2 1.421(3) . ? C36 C37 1.380(4) . ? C36 H36 0.9500 . ? C37 C38 1.380(4) . ? C37 H37 0.9500 . ? C38 C39 1.376(4) . ? C38 H38 0.9500 . ? C39 C40 1.386(3) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41 C46 1.378(3) . ? C41 C42 1.382(3) . ? C41 N2 1.440(3) . ? C42 C43 1.379(4) . ? C42 H42 0.9500 . ? C43 C44 1.382(4) . ? C43 H43 0.9500 . ? C44 C45 1.385(4) . ? C44 H44 0.9500 . ? C45 C46 1.380(4) . ? C45 H45 0.9500 . ? C46 H46 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 N1 C1 C2 178.2(3) . . ? C3 C2 C1 120.4(2) . . ? C3 C2 C7 119.1(2) . . ? C1 C2 C7 120.3(3) . . ? C4 C3 C2 120.2(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 121.8(2) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C4 C5 C6 117.3(2) . . ? C4 C5 C8 121.0(2) . . ? C6 C5 C8 121.6(2) . . ? C7 C6 C5 121.6(2) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C2 119.9(2) . . ? C6 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? C13 C8 C9 117.2(2) . . ? C13 C8 C5 120.1(2) . . ? C9 C8 C5 122.8(2) . . ? C10 C9 C8 120.0(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 122.9(2) . . ? C9 C10 H10 118.5 . . ? C11 C10 H10 118.5 . . ? C12 C11 C10 117.7(2) . . ? C12 C11 C30 126.5(2) . . ? C10 C11 C30 115.7(2) . . ? C11 C12 C13 117.4(2) . . ? C11 C12 C14 124.54(19) . . ? C13 C12 C14 117.60(18) . . ? C8 C13 C12 124.7(2) . . ? C8 C13 H13 117.6 . . ? C12 C13 H13 117.6 . . ? C15 C14 C26 101.07(16) . . ? C15 C14 C12 109.46(16) . . ? C26 C14 C12 108.08(17) . . ? C15 C14 C27 109.18(17) . . ? C26 C14 C27 111.25(16) . . ? C12 C14 C27 116.66(17) . . ? C20 C15 C16 120.4(2) . . ? C20 C15 C14 111.22(19) . . ? C16 C15 C14 128.40(19) . . ? C15 C16 C17 119.0(2) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C18 C17 C16 120.5(2) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 120.9(2) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C18 C19 C20 118.9(2) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? C15 C20 C19 120.2(2) . . ? C15 C20 C21 108.87(18) . . ? C19 C20 C21 130.9(2) . . ? C22 C21 C26 120.2(2) . . ? C22 C21 C20 130.3(2) . . ? C26 C21 C20 109.53(18) . . ? C23 C22 C21 119.1(2) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C22 C23 C24 120.7(2) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C23 C24 C25 120.2(2) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C26 C25 C24 119.7(2) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C21 120.1(2) . . ? C25 C26 C14 130.6(2) . . ? C21 C26 C14 109.31(18) . . ? C28 C27 C34 118.05(19) . . ? C28 C27 C14 125.3(2) . . ? C34 C27 C14 116.42(18) . . ? C31 C28 C27 117.2(2) . . ? C31 C28 C29 116.58(19) . . ? C27 C28 C29 126.2(2) . . ? C30 C29 C28 130.4(2) . . ? C30 C29 H29 114.8 . . ? C28 C29 H29 114.8 . . ? C29 C30 C11 128.8(2) . . ? C29 C30 H30 115.6 . . ? C11 C30 H30 115.6 . . ? C32 C31 C28 124.5(2) . . ? C32 C31 H31 117.8 . . ? C28 C31 H31 117.8 . . ? C31 C32 C33 118.6(2) . . ? C31 C32 H32 120.7 . . ? C33 C32 H32 120.7 . . ? C32 C33 C34 117.9(2) . . ? C32 C33 N2 122.4(2) . . ? C34 C33 N2 119.7(2) . . ? C33 C34 C27 123.6(2) . . ? C33 C34 H34 118.2 . . ? C27 C34 H34 118.2 . . ? C40 C35 C36 118.7(2) . . ? C40 C35 N2 119.9(2) . . ? C36 C35 N2 121.3(2) . . ? C37 C36 C35 120.9(3) . . ? C37 C36 H36 119.6 . . ? C35 C36 H36 119.6 . . ? C36 C37 C38 120.0(3) . . ? C36 C37 H37 120.0 . . ? C38 C37 H37 120.0 . . ? C37 C38 C39 119.8(2) . . ? C37 C38 H38 120.1 . . ? C39 C38 H38 120.1 . . ? C40 C39 C38 120.5(2) . . ? C40 C39 H39 119.8 . . ? C38 C39 H39 119.8 . . ? C35 C40 C39 120.1(2) . . ? C35 C40 H40 119.9 . . ? C39 C40 H40 119.9 . . ? C46 C41 C42 120.2(2) . . ? C46 C41 N2 120.1(2) . . ? C42 C41 N2 119.7(2) . . ? C41 C42 C43 119.6(2) . . ? C41 C42 H42 120.2 . . ? C43 C42 H42 120.2 . . ? C44 C43 C42 120.6(3) . . ? C44 C43 H43 119.7 . . ? C42 C43 H43 119.7 . . ? C43 C44 C45 119.4(2) . . ? C43 C44 H44 120.3 . . ? C45 C44 H44 120.3 . . ? C46 C45 C44 120.1(2) . . ? C46 C45 H45 119.9 . . ? C44 C45 H45 119.9 . . ? C41 C46 C45 120.0(2) . . ? C41 C46 H46 120.0 . . ? C45 C46 H46 120.0 . . ? C33 N2 C35 123.21(19) . . ? C33 N2 C41 120.33(18) . . ? C35 N2 C41 115.95(18) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.489 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.107 data_13136 _database_code_depnum_ccdc_archive 'CCDC 876490' #TrackingRef '10761_web_deposit_cif_file_2_Chien-TienChen_1334635330.13136_3c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H35 N3' _chemical_formula_sum 'C52 H35 N3' _chemical_formula_weight 701.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 10.7889(3) _cell_length_b 19.9049(5) _cell_length_c 17.5852(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.6210(10) _cell_angle_gamma 90.00 _cell_volume 3618.67(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13810 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour yellow-brown _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8824 _exptl_absorpt_correction_T_max 1.0678 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17767 _diffrn_reflns_av_R_equivalents 0.0735 _diffrn_reflns_av_sigmaI/netI 0.0843 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.06 _reflns_number_total 6383 _reflns_number_gt 3756 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1147P)^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 6383 _refine_ls_number_parameters 496 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1304 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.2234 _refine_ls_wR_factor_gt 0.1690 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2697(3) -0.19754(19) 0.2302(2) 0.0418(9) Uani 1 1 d . . . C2 C 0.2143(4) -0.2555(2) 0.1895(2) 0.0521(10) Uani 1 1 d . . . H2 H 0.1285 -0.2556 0.1585 0.063 Uiso 1 1 calc R . . C3 C 0.2887(4) -0.3119(2) 0.1960(2) 0.0571(11) Uani 1 1 d . . . H3 H 0.2532 -0.3506 0.1685 0.068 Uiso 1 1 calc R . . C4 C 0.4169(4) -0.3126(2) 0.2431(3) 0.0592(11) Uani 1 1 d . . . H4 H 0.4650 -0.3519 0.2470 0.071 Uiso 1 1 calc R . . C5 C 0.4735(4) -0.2565(2) 0.2838(2) 0.0520(10) Uani 1 1 d . . . H5 H 0.5587 -0.2571 0.3157 0.062 Uiso 1 1 calc R . . C6 C 0.3989(3) -0.19924(18) 0.2755(2) 0.0405(9) Uani 1 1 d . . . C7 C 0.5434(3) -0.11444(19) 0.3624(2) 0.0438(9) Uani 1 1 d . . . C8 C 0.6610(3) -0.1277(2) 0.3501(2) 0.0558(11) Uani 1 1 d . . . H8 H 0.6654 -0.1482 0.3035 0.067 Uiso 1 1 calc R . . C9 C 0.7735(4) -0.1100(3) 0.4081(3) 0.0706(13) Uani 1 1 d . . . H9 H 0.8535 -0.1196 0.4007 0.085 Uiso 1 1 calc R . . C10 C 0.7674(4) -0.0784(3) 0.4762(3) 0.0735(14) Uani 1 1 d . . . H10 H 0.8433 -0.0663 0.5145 0.088 Uiso 1 1 calc R . . C11 C 0.6499(4) -0.0645(2) 0.4881(2) 0.0651(12) Uani 1 1 d . . . H11 H 0.6462 -0.0425 0.5340 0.078 Uiso 1 1 calc R . . C12 C 0.5377(4) -0.0831(2) 0.4324(2) 0.0516(10) Uani 1 1 d . . . H12 H 0.4581 -0.0748 0.4412 0.062 Uiso 1 1 calc R . . C13 C 0.3134(3) -0.09713(18) 0.2753(2) 0.0391(8) Uani 1 1 d . . . C14 C 0.3053(3) -0.02495(18) 0.28884(19) 0.0373(8) Uani 1 1 d . . . C15 C 0.1930(3) 0.0026(2) 0.2992(2) 0.0444(9) Uani 1 1 d . . . H15 H 0.1219 -0.0246 0.2970 0.053 Uiso 1 1 calc R . . C16 C 0.1880(3) 0.0702(2) 0.3128(2) 0.0451(9) Uani 1 1 d . . . H16 H 0.1129 0.0879 0.3206 0.054 Uiso 1 1 calc R . . C17 C 0.2919(3) 0.11405(18) 0.31550(19) 0.0378(8) Uani 1 1 d . . . C18 C 0.4041(3) 0.08731(18) 0.30004(18) 0.0336(8) Uani 1 1 d . . . C19 C 0.4069(3) 0.01779(18) 0.28819(18) 0.0366(8) Uani 1 1 d . . . H19 H 0.4807 -0.0008 0.2794 0.044 Uiso 1 1 calc R . . C20 C 0.2739(3) 0.18302(19) 0.3356(2) 0.0469(9) Uani 1 1 d . . . H20 H 0.2185 0.1895 0.3669 0.056 Uiso 1 1 calc R . . C21 C 0.3256(3) 0.2385(2) 0.3155(2) 0.0474(9) Uani 1 1 d . . . H21 H 0.3061 0.2783 0.3375 0.057 Uiso 1 1 calc R . . C22 C 0.4086(3) 0.24521(18) 0.2638(2) 0.0395(8) Uani 1 1 d . . . C23 C 0.4897(3) 0.19461(17) 0.24825(19) 0.0344(8) Uani 1 1 d . . . C24 C 0.5249(3) 0.12987(17) 0.29939(18) 0.0334(8) Uani 1 1 d . . . C25 C 0.6189(3) 0.08582(17) 0.2702(2) 0.0371(8) Uani 1 1 d . . . C26 C 0.6034(3) 0.05743(19) 0.1959(2) 0.0465(9) Uani 1 1 d . . . H26 H 0.5268 0.0635 0.1556 0.056 Uiso 1 1 calc R . . C27 C 0.7037(4) 0.0199(2) 0.1824(3) 0.0582(11) Uani 1 1 d . . . H27 H 0.6946 0.0020 0.1323 0.070 Uiso 1 1 calc R . . C28 C 0.8153(4) 0.0089(2) 0.2417(3) 0.0672(13) Uani 1 1 d . . . H28 H 0.8813 -0.0163 0.2315 0.081 Uiso 1 1 calc R . . C29 C 0.8308(4) 0.0346(2) 0.3159(3) 0.0612(12) Uani 1 1 d . . . H29 H 0.9063 0.0263 0.3563 0.073 Uiso 1 1 calc R . . C30 C 0.7327(3) 0.07332(18) 0.3304(2) 0.0432(9) Uani 1 1 d . . . C31 C 0.7254(3) 0.1093(2) 0.4013(2) 0.0477(10) Uani 1 1 d . . . C32 C 0.8186(4) 0.1132(3) 0.4751(3) 0.0742(14) Uani 1 1 d . . . H32 H 0.8949 0.0886 0.4853 0.089 Uiso 1 1 calc R . . C33 C 0.7947(5) 0.1541(3) 0.5323(3) 0.0873(16) Uani 1 1 d . . . H33 H 0.8547 0.1568 0.5821 0.105 Uiso 1 1 calc R . . C34 C 0.6829(5) 0.1911(3) 0.5164(3) 0.0794(15) Uani 1 1 d . . . H34 H 0.6698 0.2196 0.5553 0.095 Uiso 1 1 calc R . . C35 C 0.5877(4) 0.1869(2) 0.4429(2) 0.0576(11) Uani 1 1 d . . . H35 H 0.5119 0.2119 0.4332 0.069 Uiso 1 1 calc R . . C36 C 0.6091(3) 0.14503(18) 0.3853(2) 0.0395(8) Uani 1 1 d . . . C37 C 0.5456(3) 0.20672(18) 0.18691(19) 0.0386(8) Uani 1 1 d . . . H37 H 0.6013 0.1746 0.1767 0.046 Uiso 1 1 calc R . . C38 C 0.5217(3) 0.26468(19) 0.14033(19) 0.0433(9) Uani 1 1 d . . . C39 C 0.4503(3) 0.31587(19) 0.1605(2) 0.0469(9) Uani 1 1 d . . . H39 H 0.4391 0.3566 0.1334 0.056 Uiso 1 1 calc R . . C40 C 0.3964(3) 0.30526(19) 0.2213(2) 0.0471(9) Uani 1 1 d . . . H40 H 0.3491 0.3400 0.2349 0.057 Uiso 1 1 calc R . . C41 C 0.5711(3) 0.21108(19) 0.02623(19) 0.0436(9) Uani 1 1 d . . . C42 C 0.4734(4) 0.1644(2) 0.0145(2) 0.0489(10) Uani 1 1 d . . . H42 H 0.4060 0.1710 0.0370 0.059 Uiso 1 1 calc R . . C43 C 0.4751(4) 0.1077(2) -0.0303(2) 0.0613(12) Uani 1 1 d . . . H43 H 0.4095 0.0760 -0.0374 0.074 Uiso 1 1 calc R . . C44 C 0.5727(4) 0.0979(2) -0.0645(2) 0.0669(12) Uani 1 1 d . . . H44 H 0.5736 0.0594 -0.0944 0.080 Uiso 1 1 calc R . . C45 C 0.6686(4) 0.1445(2) -0.0548(2) 0.0650(12) Uani 1 1 d . . . H45 H 0.7341 0.1382 -0.0789 0.078 Uiso 1 1 calc R . . C46 C 0.6688(4) 0.2013(2) -0.0090(2) 0.0546(11) Uani 1 1 d . . . H46 H 0.7347 0.2328 -0.0020 0.066 Uiso 1 1 calc R . . C47 C 0.5994(3) 0.33333(19) 0.0474(2) 0.0434(9) Uani 1 1 d . . . C48 C 0.5474(4) 0.3530(2) -0.0302(2) 0.0569(11) Uani 1 1 d . . . H48 H 0.4952 0.3232 -0.0663 0.068 Uiso 1 1 calc R . . C49 C 0.5714(4) 0.4163(2) -0.0555(2) 0.0623(12) Uani 1 1 d . . . H49 H 0.5364 0.4286 -0.1083 0.075 Uiso 1 1 calc R . . C50 C 0.6467(4) 0.4607(2) -0.0025(3) 0.0666(12) Uani 1 1 d . . . H50 H 0.6623 0.5035 -0.0188 0.080 Uiso 1 1 calc R . . C51 C 0.6992(4) 0.4412(2) 0.0755(3) 0.0630(12) Uani 1 1 d . . . H51 H 0.7502 0.4712 0.1117 0.076 Uiso 1 1 calc R . . C52 C 0.6769(4) 0.3781(2) 0.1001(2) 0.0536(10) Uani 1 1 d . . . H52 H 0.7141 0.3653 0.1526 0.064 Uiso 1 1 calc R . . N1 N 0.2180(3) -0.13356(16) 0.23113(17) 0.0458(8) Uani 1 1 d . . . N2 N 0.4266(3) -0.13383(15) 0.30479(17) 0.0415(7) Uani 1 1 d . . . N3 N 0.5714(3) 0.26908(16) 0.07383(17) 0.0508(8) 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 0.046(2) 0.038(2) 0.039(2) 0.0064(17) 0.0103(16) -0.0044(18) C2 0.055(2) 0.046(3) 0.051(2) 0.0011(19) 0.0076(18) -0.014(2) C3 0.073(3) 0.036(3) 0.063(3) -0.006(2) 0.023(2) -0.010(2) C4 0.061(3) 0.037(3) 0.082(3) 0.000(2) 0.023(2) 0.003(2) C5 0.051(2) 0.037(2) 0.063(2) 0.003(2) 0.0099(18) 0.000(2) C6 0.046(2) 0.034(2) 0.041(2) 0.0018(16) 0.0118(16) -0.0035(17) C7 0.043(2) 0.040(2) 0.044(2) 0.0025(17) 0.0054(16) -0.0067(17) C8 0.048(2) 0.058(3) 0.061(3) -0.008(2) 0.0156(19) -0.008(2) C9 0.043(2) 0.083(4) 0.081(3) 0.002(3) 0.011(2) -0.007(2) C10 0.057(3) 0.082(4) 0.065(3) 0.001(3) -0.008(2) -0.013(3) C11 0.074(3) 0.070(3) 0.042(2) 0.005(2) 0.000(2) -0.006(3) C12 0.052(2) 0.057(3) 0.043(2) 0.009(2) 0.0086(18) 0.006(2) C13 0.0372(19) 0.039(2) 0.042(2) 0.0055(17) 0.0128(16) -0.0024(17) C14 0.0378(19) 0.035(2) 0.0380(19) 0.0020(16) 0.0091(15) -0.0015(16) C15 0.0349(19) 0.047(3) 0.049(2) 0.0064(18) 0.0086(16) -0.0046(18) C16 0.0367(19) 0.046(3) 0.055(2) 0.0070(19) 0.0164(16) 0.0039(18) C17 0.0388(19) 0.041(2) 0.0336(18) 0.0050(16) 0.0102(14) 0.0023(17) C18 0.0327(17) 0.036(2) 0.0316(17) 0.0038(15) 0.0078(13) 0.0020(15) C19 0.0379(18) 0.037(2) 0.0350(18) 0.0009(16) 0.0099(14) -0.0031(16) C20 0.052(2) 0.042(2) 0.055(2) 0.0024(18) 0.0270(18) 0.0062(19) C21 0.061(2) 0.033(2) 0.054(2) -0.0040(18) 0.0273(19) 0.0053(19) C22 0.0454(19) 0.029(2) 0.048(2) -0.0020(16) 0.0191(16) -0.0001(17) C23 0.0398(18) 0.028(2) 0.0353(18) -0.0024(15) 0.0112(14) 0.0004(15) C24 0.0347(17) 0.032(2) 0.0344(18) 0.0013(15) 0.0109(14) -0.0014(15) C25 0.0353(18) 0.030(2) 0.047(2) 0.0044(16) 0.0148(15) -0.0032(15) C26 0.047(2) 0.041(2) 0.056(2) -0.0045(19) 0.0215(18) -0.0026(18) C27 0.058(3) 0.043(3) 0.081(3) -0.017(2) 0.033(2) -0.004(2) C28 0.046(2) 0.049(3) 0.113(4) -0.010(3) 0.032(3) 0.004(2) C29 0.039(2) 0.053(3) 0.087(3) 0.009(2) 0.010(2) 0.005(2) C30 0.0357(19) 0.036(2) 0.056(2) 0.0066(18) 0.0103(17) -0.0026(17) C31 0.046(2) 0.045(3) 0.046(2) 0.0068(18) 0.0038(17) -0.0088(19) C32 0.059(3) 0.079(4) 0.068(3) -0.001(3) -0.011(2) -0.005(2) C33 0.082(4) 0.097(5) 0.059(3) -0.007(3) -0.018(3) -0.020(3) C34 0.098(4) 0.084(4) 0.049(3) -0.022(3) 0.010(3) -0.030(3) C35 0.066(3) 0.060(3) 0.045(2) -0.004(2) 0.013(2) -0.010(2) C36 0.044(2) 0.035(2) 0.0373(19) 0.0005(16) 0.0087(15) -0.0101(17) C37 0.0460(19) 0.031(2) 0.042(2) 0.0008(16) 0.0174(16) 0.0005(16) C38 0.053(2) 0.039(2) 0.0392(19) -0.0010(17) 0.0159(16) -0.0044(18) C39 0.059(2) 0.033(2) 0.050(2) 0.0080(17) 0.0163(18) 0.0029(18) C40 0.054(2) 0.032(2) 0.060(2) 0.0012(18) 0.0237(19) 0.0046(18) C41 0.057(2) 0.039(2) 0.0346(19) 0.0040(16) 0.0123(17) -0.0004(19) C42 0.051(2) 0.050(3) 0.047(2) -0.0040(19) 0.0163(17) -0.005(2) C43 0.063(3) 0.056(3) 0.061(3) -0.015(2) 0.012(2) -0.012(2) C44 0.086(3) 0.053(3) 0.063(3) -0.017(2) 0.023(2) 0.002(3) C45 0.079(3) 0.065(3) 0.060(3) -0.008(2) 0.035(2) 0.004(3) C46 0.064(2) 0.051(3) 0.055(2) -0.003(2) 0.027(2) -0.010(2) C47 0.055(2) 0.038(2) 0.040(2) -0.0011(17) 0.0178(17) -0.0016(19) C48 0.076(3) 0.048(3) 0.041(2) -0.0004(19) 0.0090(19) -0.012(2) C49 0.091(3) 0.050(3) 0.047(2) 0.008(2) 0.022(2) 0.000(2) C50 0.089(3) 0.046(3) 0.076(3) 0.005(2) 0.041(3) -0.011(2) C51 0.071(3) 0.056(3) 0.064(3) -0.010(2) 0.024(2) -0.022(2) C52 0.064(2) 0.052(3) 0.042(2) 0.0002(19) 0.0108(19) -0.010(2) N1 0.0413(16) 0.041(2) 0.0507(18) 0.0004(15) 0.0060(14) -0.0061(15) N2 0.0398(16) 0.0348(19) 0.0463(17) -0.0002(14) 0.0064(13) -0.0036(14) N3 0.083(2) 0.0330(19) 0.0432(17) 0.0027(15) 0.0290(16) -0.0074(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.393(5) . ? C1 C6 1.394(5) . ? C1 C2 1.398(5) . ? C2 C3 1.366(5) . ? C2 H2 0.9300 . ? C3 C4 1.395(6) . ? C3 H3 0.9300 . ? C4 C5 1.372(5) . ? C4 H4 0.9300 . ? C5 C6 1.379(5) . ? C5 H5 0.9300 . ? C6 N2 1.400(4) . ? C7 C8 1.372(5) . ? C7 C12 1.397(5) . ? C7 N2 1.426(4) . ? C8 C9 1.389(6) . ? C8 H8 0.9300 . ? C9 C10 1.371(6) . ? C9 H9 0.9300 . ? C10 C11 1.371(6) . ? C10 H10 0.9300 . ? C11 C12 1.372(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 N1 1.316(4) . ? C13 N2 1.390(4) . ? C13 C14 1.463(5) . ? C14 C15 1.388(5) . ? C14 C19 1.390(4) . ? C15 C16 1.371(5) . ? C15 H15 0.9300 . ? C16 C17 1.410(5) . ? C16 H16 0.9300 . ? C17 C18 1.419(4) . ? C17 C20 1.445(5) . ? C18 C19 1.401(5) . ? C18 C24 1.557(4) . ? C19 H19 0.9300 . ? C20 C21 1.330(5) . ? C20 H20 0.9300 . ? C21 C22 1.454(4) . ? C21 H21 0.9300 . ? C22 C40 1.396(5) . ? C22 C23 1.411(4) . ? C23 C37 1.399(4) . ? C23 C24 1.555(5) . ? C24 C25 1.536(4) . ? C24 C36 1.553(4) . ? C25 C26 1.389(5) . ? C25 C30 1.394(5) . ? C26 C27 1.390(5) . ? C26 H26 0.9300 . ? C27 C28 1.367(6) . ? C27 H27 0.9300 . ? C28 C29 1.365(6) . ? C28 H28 0.9300 . ? C29 C30 1.391(5) . ? C29 H29 0.9300 . ? C30 C31 1.460(5) . ? C31 C36 1.399(5) . ? C31 C32 1.399(6) . ? C32 C33 1.374(7) . ? C32 H32 0.9300 . ? C33 C34 1.372(7) . ? C33 H33 0.9300 . ? C34 C35 1.405(6) . ? C34 H34 0.9300 . ? C35 C36 1.382(5) . ? C35 H35 0.9300 . ? C37 C38 1.396(5) . ? C37 H37 0.9300 . ? C38 C39 1.384(5) . ? C38 N3 1.421(4) . ? C39 C40 1.371(5) . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? C41 C42 1.376(5) . ? C41 C46 1.380(5) . ? C41 N3 1.425(5) . ? C42 C43 1.380(5) . ? C42 H42 0.9300 . ? C43 C44 1.367(5) . ? C43 H43 0.9300 . ? C44 C45 1.365(6) . ? C44 H44 0.9300 . ? C45 C46 1.387(6) . ? C45 H45 0.9300 . ? C46 H46 0.9300 . ? C47 C48 1.375(5) . ? C47 C52 1.381(5) . ? C47 N3 1.423(5) . ? C48 C49 1.386(5) . ? C48 H48 0.9300 . ? C49 C50 1.370(6) . ? C49 H49 0.9300 . ? C50 C51 1.381(6) . ? C50 H50 0.9300 . ? C51 C52 1.372(6) . ? C51 H51 0.9300 . ? C52 H52 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C6 110.7(3) . . ? N1 C1 C2 130.3(3) . . ? C6 C1 C2 118.9(4) . . ? C3 C2 C1 118.7(4) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 121.1(4) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 121.3(4) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 117.3(3) . . ? C4 C5 H5 121.4 . . ? C6 C5 H5 121.4 . . ? C5 C6 C1 122.6(3) . . ? C5 C6 N2 132.3(3) . . ? C1 C6 N2 105.1(3) . . ? C8 C7 C12 120.0(3) . . ? C8 C7 N2 120.3(3) . . ? C12 C7 N2 119.6(3) . . ? C7 C8 C9 119.2(4) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 120.5(4) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 120.2(4) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C12 120.2(4) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 119.8(4) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? N1 C13 N2 112.7(3) . . ? N1 C13 C14 124.3(3) . . ? N2 C13 C14 122.9(3) . . ? C15 C14 C19 118.6(3) . . ? C15 C14 C13 120.3(3) . . ? C19 C14 C13 121.0(3) . . ? C16 C15 C14 119.3(3) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 122.9(3) . . ? C15 C16 H16 118.6 . . ? C17 C16 H16 118.6 . . ? C16 C17 C18 118.4(3) . . ? C16 C17 C20 115.8(3) . . ? C18 C17 C20 125.8(3) . . ? C19 C18 C17 117.0(3) . . ? C19 C18 C24 118.9(3) . . ? C17 C18 C24 124.0(3) . . ? C14 C19 C18 123.6(3) . . ? C14 C19 H19 118.2 . . ? C18 C19 H19 118.2 . . ? C21 C20 C17 128.9(3) . . ? C21 C20 H20 115.5 . . ? C17 C20 H20 115.5 . . ? C20 C21 C22 128.5(3) . . ? C20 C21 H21 115.8 . . ? C22 C21 H21 115.8 . . ? C40 C22 C23 118.4(3) . . ? C40 C22 C21 115.7(3) . . ? C23 C22 C21 125.7(3) . . ? C37 C23 C22 117.0(3) . . ? C37 C23 C24 120.1(3) . . ? C22 C23 C24 122.8(3) . . ? C25 C24 C36 100.2(2) . . ? C25 C24 C23 110.8(2) . . ? C36 C24 C23 112.3(3) . . ? C25 C24 C18 109.0(3) . . ? C36 C24 C18 110.9(2) . . ? C23 C24 C18 112.9(2) . . ? C26 C25 C30 119.0(3) . . ? C26 C25 C24 129.3(3) . . ? C30 C25 C24 111.8(3) . . ? C25 C26 C27 119.3(4) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? C28 C27 C26 121.0(4) . . ? C28 C27 H27 119.5 . . ? C26 C27 H27 119.5 . . ? C27 C28 C29 120.6(4) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 119.7 . . ? C28 C29 C30 119.4(4) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? C29 C30 C25 120.7(4) . . ? C29 C30 C31 131.2(3) . . ? C25 C30 C31 108.0(3) . . ? C36 C31 C32 121.7(4) . . ? C36 C31 C30 110.0(3) . . ? C32 C31 C30 128.3(4) . . ? C33 C32 C31 118.4(4) . . ? C33 C32 H32 120.8 . . ? C31 C32 H32 120.8 . . ? C32 C33 C34 120.5(4) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C33 C34 C35 121.6(5) . . ? C33 C34 H34 119.2 . . ? C35 C34 H34 119.2 . . ? C36 C35 C34 118.6(4) . . ? C36 C35 H35 120.7 . . ? C34 C35 H35 120.7 . . ? C35 C36 C31 119.2(3) . . ? C35 C36 C24 131.0(3) . . ? C31 C36 C24 109.8(3) . . ? C38 C37 C23 123.2(3) . . ? C38 C37 H37 118.4 . . ? C23 C37 H37 118.4 . . ? C39 C38 C37 118.8(3) . . ? C39 C38 N3 122.3(3) . . ? C37 C38 N3 119.0(3) . . ? C40 C39 C38 118.5(3) . . ? C40 C39 H39 120.7 . . ? C38 C39 H39 120.7 . . ? C39 C40 C22 123.6(3) . . ? C39 C40 H40 118.2 . . ? C22 C40 H40 118.2 . . ? C42 C41 C46 119.2(4) . . ? C42 C41 N3 120.5(3) . . ? C46 C41 N3 120.3(3) . . ? C41 C42 C43 120.2(3) . . ? C41 C42 H42 119.9 . . ? C43 C42 H42 119.9 . . ? C44 C43 C42 120.4(4) . . ? C44 C43 H43 119.8 . . ? C42 C43 H43 119.8 . . ? C45 C44 C43 120.0(4) . . ? C45 C44 H44 120.0 . . ? C43 C44 H44 120.0 . . ? C44 C45 C46 120.1(4) . . ? C44 C45 H45 119.9 . . ? C46 C45 H45 119.9 . . ? C41 C46 C45 120.1(4) . . ? C41 C46 H46 120.0 . . ? C45 C46 H46 120.0 . . ? C48 C47 C52 118.7(4) . . ? C48 C47 N3 121.0(3) . . ? C52 C47 N3 120.3(3) . . ? C47 C48 C49 121.1(4) . . ? C47 C48 H48 119.5 . . ? C49 C48 H48 119.5 . . ? C50 C49 C48 119.8(4) . . ? C50 C49 H49 120.1 . . ? C48 C49 H49 120.1 . . ? C49 C50 C51 119.3(4) . . ? C49 C50 H50 120.4 . . ? C51 C50 H50 120.4 . . ? C52 C51 C50 120.8(4) . . ? C52 C51 H51 119.6 . . ? C50 C51 H51 119.6 . . ? C51 C52 C47 120.4(4) . . ? C51 C52 H52 119.8 . . ? C47 C52 H52 119.8 . . ? C13 N1 C1 105.2(3) . . ? C13 N2 C6 106.2(3) . . ? C13 N2 C7 128.8(3) . . ? C6 N2 C7 124.4(3) . . ? C38 N3 C47 119.3(3) . . ? C38 N3 C41 119.7(3) . . ? C47 N3 C41 120.1(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.463 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.167 data_a8942 _database_code_depnum_ccdc_archive 'CCDC 876491' #TrackingRef '10762_web_deposit_cif_file_3_Chien-TienChen_1334635330.a8942_3d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C58 H39 N3' _chemical_formula_sum 'C58 H39 N3' _chemical_formula_weight 777.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7569(3) _cell_length_b 13.6042(3) _cell_length_c 16.6420(4) _cell_angle_alpha 106.930(2) _cell_angle_beta 104.183(2) _cell_angle_gamma 90.917(2) _cell_volume 2248.77(10) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9611 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7552 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.02 _reflns_number_total 7552 _reflns_number_gt 5299 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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. ; # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.033 0.500 0.500 322 36 ' ' _platon_squeeze_details ; the SQUEEZE removed the contributions of 36 electrons from the reflection file, which corresponds with 36/2 = 18 electrons or 18.0/18 = 1 H2O molecules per asymmetric unit. Since there are two independent molecules in the asymmetric unit, the overall correct formulation for this complex would be C58H39N3-0.5H2O. The contribution of the H2O disordered solvent is removed by the SQUEEZE ; _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^)+(0.1653P)^2^+0.8037P] 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 7552 _refine_ls_number_parameters 550 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1723 _refine_ls_wR_factor_gt 0.1486 _refine_ls_goodness_of_fit_ref 0.687 _refine_ls_restrained_S_all 0.687 _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 0.55379(17) 0.72486(13) 1.12977(11) 0.0351(4) Uani 1 1 d . . . N2 N 0.12130(17) 0.88444(14) 0.30971(11) 0.0374(4) Uani 1 1 d . . . N3 N 0.21984(18) 0.73917(14) 0.30475(12) 0.0399(5) Uani 1 1 d . . . C15 C 0.64542(18) 0.86537(15) 0.98610(12) 0.0274(4) Uani 1 1 d . . . C18 C 0.6651(2) 0.89451(16) 1.16417(13) 0.0326(5) Uani 1 1 d . . . H18 H 0.6683 0.9073 1.2239 0.039 Uiso 1 1 calc R . . C23 C 0.5382(2) 0.90132(16) 0.75872(13) 0.0316(5) Uani 1 1 d . . . H23 H 0.4889 0.8361 0.7347 0.038 Uiso 1 1 calc R . . C24 C 0.5265(2) 0.96698(16) 0.70751(13) 0.0314(5) Uani 1 1 d . . . C13 C 0.60342(19) 0.80347(15) 1.10263(13) 0.0299(5) Uani 1 1 d . . . C21 C 0.68988(19) 1.02190(15) 0.87779(13) 0.0296(5) Uani 1 1 d . . . C25 C 0.5968(2) 1.06331(16) 0.74354(13) 0.0332(5) Uani 1 1 d . . . H25 H 0.5900 1.1109 0.7110 0.040 Uiso 1 1 calc R . . C26 C 0.6759(2) 1.08899(16) 0.82625(13) 0.0322(5) Uani 1 1 d . . . H26 H 0.7234 1.1549 0.8499 0.039 Uiso 1 1 calc R . . C40 C 0.4421(2) 0.93461(16) 0.61742(13) 0.0341(5) Uani 1 1 d . . . C34 C 0.5578(2) 0.66134(16) 0.79633(13) 0.0340(5) Uani 1 1 d . . . C16 C 0.71587(19) 0.95370(15) 1.04913(13) 0.0297(5) Uani 1 1 d . . . C14 C 0.59434(19) 0.79139(15) 1.01526(13) 0.0287(4) Uani 1 1 d . . . H14 H 0.5510 0.7294 0.9732 0.034 Uiso 1 1 calc R . . C27 C 0.63140(19) 0.83703(15) 0.88619(12) 0.0283(5) Uani 1 1 d . . . C1 C 0.4480(2) 0.65341(16) 1.07598(13) 0.0331(5) Uani 1 1 d . . . C39 C 0.5176(2) 0.75438(15) 0.83847(12) 0.0300(5) Uani 1 1 d . . . C33 C 0.6982(2) 0.67369(16) 0.81184(13) 0.0333(5) Uani 1 1 d . . . C17 C 0.7215(2) 0.96592(16) 1.13682(13) 0.0326(5) Uani 1 1 d . . . H17 H 0.7667 1.0268 1.1795 0.039 Uiso 1 1 calc R . . C20 C 0.7812(2) 1.06166(16) 0.96277(14) 0.0344(5) Uani 1 1 d . . . H20 H 0.8434 1.1151 0.9680 0.041 Uiso 1 1 calc R . . C2 C 0.3522(2) 0.68007(17) 1.01491(14) 0.0381(5) Uani 1 1 d . . . H2 H 0.3551 0.7484 1.0112 0.046 Uiso 1 1 calc R . . C22 C 0.61766(19) 0.92505(15) 0.84284(12) 0.0284(5) Uani 1 1 d . . . C6 C 0.4369(2) 0.55406(17) 1.08299(15) 0.0389(5) Uani 1 1 d . . . H6 H 0.4999 0.5344 1.1250 0.047 Uiso 1 1 calc R . . C28 C 0.7431(2) 0.77569(15) 0.86251(12) 0.0290(5) Uani 1 1 d . . . C46 C 0.2083(2) 0.83233(17) 0.35399(14) 0.0368(5) Uani 1 1 d . . . C43 C 0.2847(2) 0.87283(17) 0.44498(13) 0.0365(5) Uani 1 1 d . . . C19 C 0.7901(2) 1.03389(16) 1.03454(14) 0.0345(5) Uani 1 1 d . . . H19 H 0.8556 1.0729 1.0839 0.041 Uiso 1 1 calc R . . C53 C 0.0756(2) 0.81807(18) 0.22609(14) 0.0373(5) Uani 1 1 d . . . C29 C 0.8728(2) 0.80828(17) 0.88317(13) 0.0347(5) Uani 1 1 d . . . H29 H 0.9040 0.8778 0.9157 0.042 Uiso 1 1 calc R . . C35 C 0.4695(2) 0.57699(18) 0.74771(15) 0.0457(6) Uani 1 1 d . . . H35 H 0.4974 0.5134 0.7192 0.055 Uiso 1 1 calc R . . C37 C 0.3000(2) 0.6800(2) 0.78329(15) 0.0474(6) Uani 1 1 d . . . H37 H 0.2107 0.6861 0.7778 0.057 Uiso 1 1 calc R . . C45 C 0.3866(2) 1.00633(18) 0.57761(14) 0.0412(5) Uani 1 1 d . . . H45 H 0.4021 1.0777 0.6092 0.049 Uiso 1 1 calc R . . C58 C 0.1372(2) 0.72844(17) 0.22402(14) 0.0370(5) Uani 1 1 d . . . C44 C 0.3098(2) 0.97580(18) 0.49342(14) 0.0422(6) Uani 1 1 d . . . H44 H 0.2735 1.0266 0.4682 0.051 Uiso 1 1 calc R . . C38 C 0.3881(2) 0.76414(17) 0.83313(14) 0.0368(5) Uani 1 1 d . . . H38 H 0.3603 0.8271 0.8629 0.044 Uiso 1 1 calc R . . C57 C 0.1144(2) 0.64739(19) 0.14685(15) 0.0449(6) Uani 1 1 d . . . H57 H 0.1569 0.5863 0.1440 0.054 Uiso 1 1 calc R . . C31 C 0.9124(2) 0.63642(19) 0.80727(16) 0.0486(6) Uani 1 1 d . . . H31 H 0.9716 0.5891 0.7894 0.058 Uiso 1 1 calc R . . C30 C 0.9564(2) 0.73724(18) 0.85529(15) 0.0424(6) Uani 1 1 d . . . H30 H 1.0457 0.7586 0.8696 0.051 Uiso 1 1 calc R . . C47 C 0.0776(2) 0.98469(19) 0.33679(14) 0.0410(5) Uani 1 1 d . . . C8 C 0.5440(3) 0.70910(17) 1.27093(15) 0.0466(6) Uani 1 1 d . . . H8 H 0.4527 0.7063 1.2540 0.056 Uiso 1 1 calc R . . C42 C 0.3398(3) 0.80058(18) 0.48486(15) 0.0478(6) Uani 1 1 d . . . H42 H 0.3234 0.7291 0.4535 0.057 Uiso 1 1 calc R . . C56 C 0.0278(2) 0.6590(2) 0.07441(15) 0.0480(6) Uani 1 1 d . . . H56 H 0.0108 0.6050 0.0208 0.058 Uiso 1 1 calc R . . C7 C 0.6153(2) 0.71691(16) 1.21341(14) 0.0389(5) Uani 1 1 d . . . C54 C -0.0118(2) 0.8300(2) 0.15337(15) 0.0475(6) Uani 1 1 d . . . H54 H -0.0533 0.8915 0.1554 0.057 Uiso 1 1 calc R . . C5 C 0.3348(2) 0.48457(18) 1.02914(17) 0.0472(6) Uani 1 1 d . . . H5 H 0.3268 0.4179 1.0358 0.057 Uiso 1 1 calc R . . C36 C 0.3400(3) 0.5873(2) 0.74150(16) 0.0538(7) Uani 1 1 d . . . H36 H 0.2782 0.5304 0.7083 0.065 Uiso 1 1 calc R . . C32 C 0.7827(2) 0.60371(18) 0.78488(15) 0.0447(6) Uani 1 1 d . . . H32 H 0.7521 0.5343 0.7515 0.054 Uiso 1 1 calc R . . C3 C 0.2532(2) 0.60791(19) 0.95983(15) 0.0457(6) Uani 1 1 d . . . H3 H 0.1904 0.6263 0.9170 0.055 Uiso 1 1 calc R . . C41 C 0.4167(3) 0.83130(18) 0.56813(15) 0.0471(6) Uani 1 1 d . . . H41 H 0.4539 0.7805 0.5930 0.057 Uiso 1 1 calc R . . C12 C 0.7483(3) 0.71804(19) 1.23898(16) 0.0504(6) Uani 1 1 d . . . H12 H 0.7975 0.7208 1.1993 0.060 Uiso 1 1 calc R . . C52 C 0.1221(3) 1.0635(2) 0.31215(17) 0.0558(7) Uani 1 1 d . . . H52 H 0.1854 1.0527 0.2802 0.067 Uiso 1 1 calc R . . C55 C -0.0348(2) 0.7479(2) 0.07839(15) 0.0510(7) Uani 1 1 d . . . H55 H -0.0956 0.7523 0.0277 0.061 Uiso 1 1 calc R . . C4 C 0.2444(3) 0.50950(19) 0.96613(16) 0.0501(6) Uani 1 1 d . . . H4 H 0.1768 0.4597 0.9275 0.060 Uiso 1 1 calc R . . C48 C -0.0153(3) 0.9993(2) 0.38192(18) 0.0580(7) Uani 1 1 d . . . H48 H -0.0466 0.9442 0.3981 0.070 Uiso 1 1 calc R . . C9 C 0.6071(4) 0.70536(19) 1.35340(16) 0.0628(9) Uani 1 1 d . . . H9 H 0.5584 0.6999 1.3927 0.075 Uiso 1 1 calc R . . C49 C -0.0627(3) 1.0944(3) 0.4035(2) 0.0748(9) Uani 1 1 d . . . H49 H -0.1266 1.1050 0.4349 0.090 Uiso 1 1 calc R . . C50 C -0.0174(3) 1.1740(3) 0.3797(2) 0.0757(9) Uani 1 1 d . . . H50 H -0.0499 1.2395 0.3948 0.091 Uiso 1 1 calc R . . C11 C 0.8100(3) 0.7152(2) 1.3211(2) 0.0703(9) Uani 1 1 d . . . H11 H 0.9012 0.7171 1.3381 0.084 Uiso 1 1 calc R . . C51 C 0.0745(3) 1.1586(2) 0.3341(2) 0.0717(9) Uani 1 1 d . . . H51 H 0.1056 1.2135 0.3176 0.086 Uiso 1 1 calc R . . C10 C 0.7393(4) 0.7095(2) 1.37866(19) 0.0738(10) Uani 1 1 d . . . H10 H 0.7817 0.7085 1.4356 0.089 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 0.0382(11) 0.0359(10) 0.0348(9) 0.0178(8) 0.0083(8) -0.0028(8) N2 0.0369(10) 0.0452(11) 0.0384(10) 0.0226(9) 0.0127(8) 0.0124(9) N3 0.0434(11) 0.0412(11) 0.0395(10) 0.0182(9) 0.0113(9) 0.0070(9) C15 0.0243(10) 0.0294(11) 0.0324(10) 0.0135(9) 0.0093(9) 0.0042(8) C18 0.0346(12) 0.0344(12) 0.0305(10) 0.0118(9) 0.0093(9) 0.0037(9) C23 0.0336(12) 0.0289(11) 0.0357(11) 0.0130(9) 0.0112(9) 0.0030(9) C24 0.0313(11) 0.0341(12) 0.0357(11) 0.0158(9) 0.0146(9) 0.0073(9) C13 0.0263(11) 0.0318(11) 0.0368(11) 0.0148(9) 0.0123(9) 0.0043(9) C21 0.0279(11) 0.0293(11) 0.0362(11) 0.0122(9) 0.0140(9) 0.0031(9) C25 0.0366(12) 0.0326(12) 0.0417(12) 0.0211(10) 0.0186(10) 0.0094(9) C26 0.0348(12) 0.0287(11) 0.0398(12) 0.0138(9) 0.0178(10) 0.0031(9) C40 0.0393(12) 0.0363(12) 0.0348(11) 0.0188(9) 0.0146(10) 0.0079(10) C34 0.0422(13) 0.0291(11) 0.0326(11) 0.0135(9) 0.0084(10) -0.0010(10) C16 0.0269(11) 0.0284(11) 0.0354(11) 0.0126(9) 0.0075(9) 0.0038(9) C14 0.0283(11) 0.0259(10) 0.0339(10) 0.0111(8) 0.0090(9) 0.0027(8) C27 0.0278(11) 0.0267(10) 0.0314(10) 0.0124(8) 0.0055(9) -0.0007(8) C1 0.0348(12) 0.0343(12) 0.0372(11) 0.0137(9) 0.0187(10) 0.0044(9) C39 0.0345(12) 0.0290(11) 0.0317(10) 0.0173(9) 0.0088(9) -0.0001(9) C33 0.0404(13) 0.0293(11) 0.0299(10) 0.0117(9) 0.0057(9) 0.0023(10) C17 0.0313(11) 0.0285(11) 0.0372(11) 0.0102(9) 0.0073(9) 0.0015(9) C20 0.0306(11) 0.0292(11) 0.0446(12) 0.0117(9) 0.0122(10) -0.0040(9) C2 0.0351(12) 0.0385(13) 0.0485(13) 0.0196(10) 0.0178(10) 0.0041(10) C22 0.0281(11) 0.0286(11) 0.0340(11) 0.0136(9) 0.0132(9) 0.0057(9) C6 0.0424(13) 0.0351(12) 0.0482(13) 0.0187(10) 0.0205(11) 0.0065(10) C28 0.0364(12) 0.0285(11) 0.0264(10) 0.0149(8) 0.0084(9) 0.0037(9) C46 0.0349(12) 0.0425(13) 0.0404(12) 0.0216(10) 0.0123(10) 0.0065(10) C43 0.0385(13) 0.0405(13) 0.0367(12) 0.0189(10) 0.0122(10) 0.0075(10) C19 0.0346(12) 0.0320(12) 0.0359(11) 0.0119(9) 0.0060(9) -0.0043(9) C53 0.0302(12) 0.0516(14) 0.0367(12) 0.0216(10) 0.0109(10) 0.0012(10) C29 0.0365(12) 0.0325(12) 0.0375(11) 0.0131(9) 0.0112(10) 0.0030(10) C35 0.0536(16) 0.0329(13) 0.0440(13) 0.0099(10) 0.0035(11) -0.0052(11) C37 0.0387(14) 0.0569(16) 0.0481(14) 0.0226(12) 0.0070(11) -0.0081(12) C45 0.0494(14) 0.0348(12) 0.0431(13) 0.0190(10) 0.0101(11) 0.0061(11) C58 0.0362(12) 0.0441(13) 0.0354(12) 0.0187(10) 0.0104(10) -0.0009(10) C44 0.0466(14) 0.0423(13) 0.0430(13) 0.0246(11) 0.0071(11) 0.0092(11) C38 0.0335(12) 0.0398(13) 0.0385(11) 0.0165(10) 0.0067(10) -0.0023(10) C57 0.0467(14) 0.0480(14) 0.0435(13) 0.0185(11) 0.0129(11) -0.0029(11) C31 0.0478(15) 0.0444(14) 0.0552(15) 0.0138(12) 0.0173(12) 0.0166(12) C30 0.0350(13) 0.0472(14) 0.0491(13) 0.0186(11) 0.0136(11) 0.0082(11) C47 0.0410(13) 0.0511(14) 0.0389(12) 0.0224(11) 0.0135(10) 0.0161(11) C8 0.0727(18) 0.0330(13) 0.0427(13) 0.0156(10) 0.0256(12) 0.0058(12) C42 0.0697(18) 0.0359(13) 0.0365(12) 0.0134(10) 0.0082(12) 0.0132(12) C56 0.0419(14) 0.0631(17) 0.0396(13) 0.0182(12) 0.0095(11) -0.0098(13) C7 0.0541(15) 0.0292(12) 0.0367(12) 0.0153(9) 0.0115(11) 0.0022(10) C54 0.0315(13) 0.0726(18) 0.0504(14) 0.0345(13) 0.0134(11) 0.0106(12) C5 0.0535(16) 0.0319(13) 0.0630(16) 0.0124(11) 0.0303(13) 0.0007(11) C36 0.0515(16) 0.0512(16) 0.0504(15) 0.0136(12) 0.0019(12) -0.0193(13) C32 0.0549(16) 0.0308(12) 0.0447(13) 0.0074(10) 0.0110(12) 0.0096(11) C3 0.0347(13) 0.0582(16) 0.0468(13) 0.0203(12) 0.0102(11) -0.0019(11) C41 0.0665(17) 0.0391(14) 0.0390(13) 0.0203(11) 0.0090(12) 0.0155(12) C12 0.0533(16) 0.0479(15) 0.0527(15) 0.0253(12) 0.0069(12) 0.0006(12) C52 0.0665(18) 0.0598(17) 0.0651(16) 0.0364(14) 0.0388(14) 0.0285(14) C55 0.0360(14) 0.083(2) 0.0373(13) 0.0279(13) 0.0040(11) -0.0028(13) C4 0.0446(15) 0.0466(15) 0.0555(15) 0.0073(12) 0.0174(12) -0.0110(12) C48 0.0578(17) 0.0669(18) 0.0641(17) 0.0283(14) 0.0321(14) 0.0167(14) C9 0.120(3) 0.0361(14) 0.0403(14) 0.0159(11) 0.0304(17) 0.0028(16) C49 0.074(2) 0.086(2) 0.084(2) 0.0295(18) 0.0493(18) 0.0372(18) C50 0.092(2) 0.076(2) 0.074(2) 0.0318(17) 0.0364(19) 0.0455(19) C11 0.080(2) 0.0588(18) 0.0651(18) 0.0335(15) -0.0110(16) -0.0043(16) C51 0.102(3) 0.0607(19) 0.080(2) 0.0414(16) 0.0472(19) 0.0402(18) C10 0.116(3) 0.0522(18) 0.0443(16) 0.0224(13) -0.0041(18) -0.0035(18) _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 C13 1.419(2) . ? N1 C1 1.414(3) . ? N1 C7 1.423(3) . ? N2 C46 1.382(3) . ? N2 C53 1.383(3) . ? N2 C47 1.432(3) . ? N3 C46 1.320(3) . ? N3 C58 1.383(3) . ? C15 C14 1.396(3) . ? C15 C16 1.402(3) . ? C15 C27 1.561(3) . ? C18 C17 1.376(3) . ? C18 C13 1.387(3) . ? C18 H18 0.9500 . ? C23 C22 1.391(3) . ? C23 C24 1.391(3) . ? C23 H23 0.9500 . ? C24 C25 1.392(3) . ? C24 C40 1.484(3) . ? C13 C14 1.393(3) . ? C21 C22 1.406(3) . ? C21 C26 1.410(3) . ? C21 C20 1.454(3) . ? C25 C26 1.370(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C40 C41 1.389(3) . ? C40 C45 1.396(3) . ? C34 C35 1.386(3) . ? C34 C39 1.389(3) . ? C34 C33 1.467(3) . ? C16 C17 1.406(3) . ? C16 C19 1.452(3) . ? C14 H14 0.9500 . ? C27 C39 1.534(3) . ? C27 C28 1.539(3) . ? C27 C22 1.560(3) . ? C1 C2 1.393(3) . ? C1 C6 1.396(3) . ? C39 C38 1.385(3) . ? C33 C32 1.383(3) . ? C33 C28 1.403(3) . ? C17 H17 0.9500 . ? C20 C19 1.336(3) . ? C20 H20 0.9500 . ? C2 C3 1.379(3) . ? C2 H2 0.9500 . ? C6 C5 1.376(3) . ? C6 H6 0.9500 . ? C28 C29 1.385(3) . ? C46 C43 1.470(3) . ? C43 C44 1.382(3) . ? C43 C42 1.401(3) . ? C19 H19 0.9500 . ? C53 C58 1.393(3) . ? C53 C54 1.391(3) . ? C29 C30 1.389(3) . ? C29 H29 0.9500 . ? C35 C36 1.384(4) . ? C35 H35 0.9500 . ? C37 C36 1.383(4) . ? C37 C38 1.387(3) . ? C37 H37 0.9500 . ? C45 C44 1.379(3) . ? C45 H45 0.9500 . ? C58 C57 1.392(3) . ? C44 H44 0.9500 . ? C38 H38 0.9500 . ? C57 C56 1.383(3) . ? C57 H57 0.9500 . ? C31 C32 1.383(3) . ? C31 C30 1.378(3) . ? C31 H31 0.9500 . ? C30 H30 0.9500 . ? C47 C48 1.374(3) . ? C47 C52 1.372(3) . ? C8 C7 1.391(3) . ? C8 C9 1.390(4) . ? C8 H8 0.9500 . ? C42 C41 1.367(3) . ? C42 H42 0.9500 . ? C56 C55 1.386(4) . ? C56 H56 0.9500 . ? C7 C12 1.387(4) . ? C54 C55 1.376(4) . ? C54 H54 0.9500 . ? C5 C4 1.371(4) . ? C5 H5 0.9500 . ? C36 H36 0.9500 . ? C32 H32 0.9500 . ? C3 C4 1.377(3) . ? C3 H3 0.9500 . ? C41 H41 0.9500 . ? C12 C11 1.377(4) . ? C12 H12 0.9500 . ? C52 C51 1.381(4) . ? C52 H52 0.9500 . ? C55 H55 0.9500 . ? C4 H4 0.9500 . ? C48 C49 1.380(4) . ? C48 H48 0.9500 . ? C9 C10 1.376(5) . ? C9 H9 0.9500 . ? C49 C50 1.376(5) . ? C49 H49 0.9500 . ? C50 C51 1.371(4) . ? C50 H50 0.9500 . ? C11 C10 1.378(5) . ? C11 H11 0.9500 . ? C51 H51 0.9500 . ? C10 H10 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 C13 N1 C1 122.32(17) . . ? C13 N1 C7 118.31(17) . . ? C1 N1 C7 119.35(16) . . ? C46 N2 C53 105.89(19) . . ? C46 N2 C47 131.80(19) . . ? C53 N2 C47 122.31(18) . . ? C46 N3 C58 105.56(18) . . ? C14 C15 C16 117.55(18) . . ? C14 C15 C27 116.75(17) . . ? C16 C15 C27 125.36(17) . . ? C17 C18 C13 118.58(19) . . ? C17 C18 H18 120.7 . . ? C13 C18 H18 120.7 . . ? C22 C23 C24 124.14(19) . . ? C22 C23 H23 117.9 . . ? C24 C23 H23 117.9 . . ? C23 C24 C25 117.78(19) . . ? C23 C24 C40 120.75(19) . . ? C25 C24 C40 121.47(18) . . ? C18 C13 C14 118.40(18) . . ? C18 C13 N1 119.77(18) . . ? C14 C13 N1 121.82(18) . . ? C22 C21 C26 118.23(18) . . ? C22 C21 C20 126.89(18) . . ? C26 C21 C20 114.87(18) . . ? C26 C25 C24 119.46(18) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C25 C26 C21 122.94(19) . . ? C25 C26 H26 118.5 . . ? C21 C26 H26 118.5 . . ? C41 C40 C45 116.9(2) . . ? C41 C40 C24 121.35(19) . . ? C45 C40 C24 121.8(2) . . ? C35 C34 C39 120.9(2) . . ? C35 C34 C33 130.5(2) . . ? C39 C34 C33 108.58(18) . . ? C17 C16 C15 118.00(18) . . ? C17 C16 C19 114.97(18) . . ? C15 C16 C19 126.97(19) . . ? C13 C14 C15 123.62(19) . . ? C13 C14 H14 118.2 . . ? C15 C14 H14 118.2 . . ? C39 C27 C28 100.26(16) . . ? C39 C27 C15 108.67(15) . . ? C28 C27 C15 110.15(15) . . ? C39 C27 C22 108.94(15) . . ? C28 C27 C22 108.39(15) . . ? C15 C27 C22 118.82(16) . . ? C2 C1 C6 118.3(2) . . ? C2 C1 N1 121.11(19) . . ? C6 C1 N1 120.6(2) . . ? C38 C39 C34 120.34(19) . . ? C38 C39 C27 127.99(19) . . ? C34 C39 C27 111.66(18) . . ? C32 C33 C28 120.7(2) . . ? C32 C33 C34 130.6(2) . . ? C28 C33 C34 108.67(19) . . ? C18 C17 C16 123.58(19) . . ? C18 C17 H17 118.2 . . ? C16 C17 H17 118.2 . . ? C19 C20 C21 129.32(19) . . ? C19 C20 H20 115.3 . . ? C21 C20 H20 115.3 . . ? C3 C2 C1 120.4(2) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C23 C22 C21 117.43(17) . . ? C23 C22 C27 116.96(17) . . ? C21 C22 C27 125.19(17) . . ? C5 C6 C1 120.1(2) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C29 C28 C33 119.9(2) . . ? C29 C28 C27 129.27(18) . . ? C33 C28 C27 110.80(18) . . ? N3 C46 N2 112.54(19) . . ? N3 C46 C43 121.4(2) . . ? N2 C46 C43 126.0(2) . . ? C44 C43 C42 117.4(2) . . ? C44 C43 C46 125.65(19) . . ? C42 C43 C46 116.9(2) . . ? C20 C19 C16 130.3(2) . . ? C20 C19 H19 114.8 . . ? C16 C19 H19 114.8 . . ? C58 C53 N2 106.34(19) . . ? C58 C53 C54 122.4(2) . . ? N2 C53 C54 131.3(2) . . ? C28 C29 C30 118.6(2) . . ? C28 C29 H29 120.7 . . ? C30 C29 H29 120.7 . . ? C34 C35 C36 118.6(2) . . ? C34 C35 H35 120.7 . . ? C36 C35 H35 120.7 . . ? C36 C37 C38 121.1(2) . . ? C36 C37 H37 119.5 . . ? C38 C37 H37 119.5 . . ? C44 C45 C40 121.4(2) . . ? C44 C45 H45 119.3 . . ? C40 C45 H45 119.3 . . ? N3 C58 C53 109.67(19) . . ? N3 C58 C57 130.2(2) . . ? C53 C58 C57 120.1(2) . . ? C45 C44 C43 121.3(2) . . ? C45 C44 H44 119.4 . . ? C43 C44 H44 119.4 . . ? C39 C38 C37 118.5(2) . . ? C39 C38 H38 120.7 . . ? C37 C38 H38 120.7 . . ? C56 C57 C58 117.6(2) . . ? C56 C57 H57 121.2 . . ? C58 C57 H57 121.2 . . ? C32 C31 C30 120.4(2) . . ? C32 C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C31 C30 C29 121.4(2) . . ? C31 C30 H30 119.3 . . ? C29 C30 H30 119.3 . . ? C48 C47 C52 120.5(2) . . ? C48 C47 N2 119.7(2) . . ? C52 C47 N2 119.6(2) . . ? C7 C8 C9 119.6(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C41 C42 C43 121.1(2) . . ? C41 C42 H42 119.5 . . ? C43 C42 H42 119.5 . . ? C57 C56 C55 121.3(2) . . ? C57 C56 H56 119.3 . . ? C55 C56 H56 119.3 . . ? C8 C7 C12 119.0(2) . . ? C8 C7 N1 120.9(2) . . ? C12 C7 N1 120.1(2) . . ? C55 C54 C53 116.4(2) . . ? C55 C54 H54 121.8 . . ? C53 C54 H54 121.8 . . ? C4 C5 C6 121.4(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C37 C36 C35 120.5(2) . . ? C37 C36 H36 119.8 . . ? C35 C36 H36 119.8 . . ? C31 C32 C33 118.9(2) . . ? C31 C32 H32 120.5 . . ? C33 C32 H32 120.5 . . ? C4 C3 C2 120.9(2) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C42 C41 C40 121.9(2) . . ? C42 C41 H41 119.1 . . ? C40 C41 H41 119.1 . . ? C11 C12 C7 120.9(3) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? C47 C52 C51 119.6(2) . . ? C47 C52 H52 120.2 . . ? C51 C52 H52 120.2 . . ? C54 C55 C56 122.1(2) . . ? C54 C55 H55 118.9 . . ? C56 C55 H55 118.9 . . ? C5 C4 C3 118.9(2) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C47 C48 C49 119.6(3) . . ? C47 C48 H48 120.2 . . ? C49 C48 H48 120.2 . . ? C10 C9 C8 120.7(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C50 C49 C48 120.1(3) . . ? C50 C49 H49 119.9 . . ? C48 C49 H49 119.9 . . ? C49 C50 C51 119.9(3) . . ? C49 C50 H50 120.0 . . ? C51 C50 H50 120.0 . . ? C10 C11 C12 120.0(3) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C50 C51 C52 120.2(3) . . ? C50 C51 H51 119.9 . . ? C52 C51 H51 119.9 . . ? C11 C10 C9 119.8(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.186 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.038 data_a8865 _database_code_depnum_ccdc_archive 'CCDC 880009' #TrackingRef '11063_web_deposit_cif_file_0_Chien-TienChen_1336029966.a8865.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H55 B N' _chemical_formula_sum 'C60 H55 B N' _chemical_formula_weight 800.86 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' B B 0.0013 0.0007 '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 13.1698(3) _cell_length_b 14.2017(3) _cell_length_c 25.4887(5) _cell_angle_alpha 100.776(2) _cell_angle_beta 96.2860(10) _cell_angle_gamma 94.685(2) _cell_volume 4629.48(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1708 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9758 _exptl_absorpt_correction_T_max 0.9968 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15353 _diffrn_reflns_av_R_equivalents 0.0761 _diffrn_reflns_av_sigmaI/netI 0.1951 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.03 _reflns_number_total 15550 _reflns_number_gt 4762 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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. ; # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.500 0.000 0.000 541 115 _platon_squeeze_details ;the SQUEEZE removed the contributions of 115.0 electrons from the reflection file, which corresponds with 115.0/4 = 28.8 electrons or 28.8/25 = 1.2 C6H14 molecules per asymmetric unit. Since there are two independent molecules in the asymmetric unit, the overall correct formulation for this complex would be C57H48BN-0.6(C6H14). ; _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^)+(0.0920P)^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 15550 _refine_ls_number_parameters 1063 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2158 _refine_ls_R_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.1993 _refine_ls_wR_factor_gt 0.1659 _refine_ls_goodness_of_fit_ref 0.805 _refine_ls_restrained_S_all 0.805 _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 B1 B 0.1556(4) 0.6973(4) 0.0455(2) 0.0666(16) Uani 1 1 d . . . B2 B 0.6168(3) 0.2349(4) 0.45517(19) 0.0513(14) Uani 1 1 d . . . C1 C 0.2209(4) 0.6095(4) 0.03173(18) 0.0662(13) Uani 1 1 d . . . C2 C 0.3155(4) 0.6021(4) 0.06160(18) 0.0735(14) Uani 1 1 d . . . C3 C 0.3668(4) 0.6837(4) 0.10659(18) 0.1015(17) Uani 1 1 d . . . H3A H 0.4295 0.6649 0.1225 0.152 Uiso 1 1 calc R . . H3B H 0.3215 0.6973 0.1335 0.152 Uiso 1 1 calc R . . H3C H 0.3817 0.7403 0.0921 0.152 Uiso 1 1 calc R . . C4 C 0.3676(4) 0.5223(5) 0.0485(2) 0.0915(17) Uani 1 1 d . . . H4 H 0.4294 0.5193 0.0692 0.110 Uiso 1 1 calc R . . C5 C 0.3335(5) 0.4479(5) 0.0069(3) 0.0937(18) Uani 1 1 d . . . C6 C 0.3919(4) 0.3605(4) -0.0060(2) 0.143(2) Uani 1 1 d . . . H6A H 0.4526 0.3674 0.0196 0.214 Uiso 1 1 calc R . . H6B H 0.4111 0.3552 -0.0416 0.214 Uiso 1 1 calc R . . H6C H 0.3490 0.3035 -0.0041 0.214 Uiso 1 1 calc R . . C7 C 0.2418(5) 0.4560(4) -0.0235(2) 0.0897(17) Uani 1 1 d . . . H7 H 0.2164 0.4066 -0.0525 0.108 Uiso 1 1 calc R . . C8 C 0.1864(4) 0.5344(4) -0.01251(19) 0.0730(14) Uani 1 1 d . . . C9 C 0.0871(4) 0.5348(4) -0.05035(17) 0.1019(17) Uani 1 1 d . . . H9A H 0.0560 0.5927 -0.0388 0.153 Uiso 1 1 calc R . . H9B H 0.0404 0.4798 -0.0494 0.153 Uiso 1 1 calc R . . H9C H 0.1031 0.5321 -0.0864 0.153 Uiso 1 1 calc R . . C10 C 0.1266(4) 0.7639(3) 0.00273(15) 0.0675(13) Uani 1 1 d . . . C11 C 0.2065(5) 0.8142(4) -0.0173(2) 0.0829(15) Uani 1 1 d . . . C12 C 0.3173(4) 0.8016(4) -0.00393(19) 0.1124(19) Uani 1 1 d . . . H12A H 0.3233 0.7538 0.0180 0.169 Uiso 1 1 calc R . . H12B H 0.3533 0.8617 0.0153 0.169 Uiso 1 1 calc R . . H12C H 0.3464 0.7813 -0.0366 0.169 Uiso 1 1 calc R . . C13 C 0.1784(6) 0.8807(4) -0.0495(2) 0.1009(19) Uani 1 1 d . . . H13 H 0.2300 0.9152 -0.0624 0.121 Uiso 1 1 calc R . . C14 C 0.0785(7) 0.8971(5) -0.0627(2) 0.1017(19) Uani 1 1 d . . . C15 C 0.0580(5) 0.9745(4) -0.0951(2) 0.156(3) Uani 1 1 d . . . H15A H -0.0146 0.9787 -0.1010 0.233 Uiso 1 1 calc R . . H15B H 0.0836 0.9583 -0.1291 0.233 Uiso 1 1 calc R . . H15C H 0.0919 1.0354 -0.0757 0.233 Uiso 1 1 calc R . . C16 C 0.0033(5) 0.8449(5) -0.04571(19) 0.0938(18) Uani 1 1 d . . . H16 H -0.0648 0.8532 -0.0562 0.113 Uiso 1 1 calc R . . C17 C 0.0242(5) 0.7788(4) -0.01295(18) 0.0817(15) Uani 1 1 d . . . C18 C -0.0670(4) 0.7215(4) 0.00128(18) 0.1096(19) Uani 1 1 d . . . H18A H -0.1293 0.7433 -0.0132 0.164 Uiso 1 1 calc R . . H18B H -0.0638 0.7305 0.0397 0.164 Uiso 1 1 calc R . . H18C H -0.0659 0.6544 -0.0137 0.164 Uiso 1 1 calc R . . C19 C 0.1212(3) 0.7251(4) 0.10310(16) 0.0620(12) Uani 1 1 d . . . C20 C 0.0755(3) 0.8094(4) 0.11915(18) 0.0769(15) Uani 1 1 d . . . H20 H 0.0647 0.8506 0.0951 0.092 Uiso 1 1 calc R . . C21 C 0.0459(3) 0.8329(3) 0.17004(17) 0.0734(14) Uani 1 1 d . . . H21 H 0.0140 0.8887 0.1792 0.088 Uiso 1 1 calc R . . C22 C 0.0629(3) 0.7741(3) 0.20809(16) 0.0559(12) Uani 1 1 d . . . C23 C 0.1145(3) 0.6926(3) 0.19574(15) 0.0510(11) Uani 1 1 d . . . C24 C 0.1381(3) 0.6685(3) 0.14274(16) 0.0588(12) Uani 1 1 d . . . H24 H 0.1670 0.6112 0.1330 0.071 Uiso 1 1 calc R . . C25 C 0.0182(3) 0.8039(3) 0.25726(17) 0.0633(13) Uani 1 1 d . . . H25 H -0.0033 0.8654 0.2616 0.076 Uiso 1 1 calc R . . C26 C 0.0024(3) 0.7585(4) 0.29736(16) 0.0613(13) Uani 1 1 d . . . H26 H -0.0262 0.7940 0.3254 0.074 Uiso 1 1 calc R . . C27 C 0.0230(3) 0.6618(3) 0.30418(15) 0.0513(11) Uani 1 1 d . . . C28 C 0.0886(3) 0.6030(4) 0.27680(14) 0.0544(12) Uani 1 1 d . . . C29 C 0.1593(3) 0.6371(3) 0.23792(16) 0.0566(12) Uani 1 1 d . . . C30 C 0.2127(5) 0.5519(4) 0.2100(2) 0.0781(16) Uani 1 1 d . . . C31 C 0.1670(5) 0.4708(5) 0.1746(2) 0.107(2) Uani 1 1 d . . . H31 H 0.0962 0.4618 0.1649 0.129 Uiso 1 1 calc R . . C32 C 0.2298(8) 0.4017(6) 0.1534(3) 0.156(4) Uani 1 1 d . . . H32 H 0.2007 0.3450 0.1303 0.188 Uiso 1 1 calc R . . C33 C 0.3351(11) 0.4184(9) 0.1670(4) 0.197(7) Uani 1 1 d . . . H33 H 0.3762 0.3737 0.1514 0.236 Uiso 1 1 calc R . . C34 C 0.3809(7) 0.4991(8) 0.2029(3) 0.177(5) Uani 1 1 d . . . H34 H 0.4517 0.5077 0.2125 0.212 Uiso 1 1 calc R . . C35 C 0.3188(6) 0.5684(6) 0.2248(3) 0.105(2) Uani 1 1 d . . . C36 C 0.3453(5) 0.6591(6) 0.2631(3) 0.102(2) Uani 1 1 d . . . C37 C 0.4414(6) 0.7078(8) 0.2911(3) 0.139(4) Uani 1 1 d . . . H37 H 0.5030 0.6834 0.2841 0.167 Uiso 1 1 calc R . . C38 C 0.4404(8) 0.7910(8) 0.3282(4) 0.161(4) Uani 1 1 d . . . H38 H 0.5015 0.8205 0.3485 0.193 Uiso 1 1 calc R . . C39 C 0.3536(5) 0.8302(5) 0.3356(2) 0.112(2) Uani 1 1 d . . . H39 H 0.3560 0.8891 0.3592 0.134 Uiso 1 1 calc R . . C40 C 0.2598(4) 0.7856(5) 0.3091(2) 0.0836(16) Uani 1 1 d . . . H40 H 0.2001 0.8135 0.3163 0.100 Uiso 1 1 calc R . . C41 C 0.2537(4) 0.7002(5) 0.2722(2) 0.0698(15) Uani 1 1 d . . . C42 C 0.0994(3) 0.5140(4) 0.29066(16) 0.0626(13) Uani 1 1 d . . . H42 H 0.1441 0.4755 0.2731 0.075 Uiso 1 1 calc R . . C43 C 0.0481(3) 0.4781(4) 0.32903(16) 0.0627(13) Uani 1 1 d . . . C44 C -0.0175(3) 0.5376(4) 0.35557(16) 0.0675(14) Uani 1 1 d . . . H44 H -0.0549 0.5168 0.3810 0.081 Uiso 1 1 calc R . . C45 C -0.0261(3) 0.6270(4) 0.34363(16) 0.0603(13) Uani 1 1 d . . . H45 H -0.0671 0.6671 0.3630 0.072 Uiso 1 1 calc R . . C46 C 0.0882(5) 0.3127(4) 0.2989(2) 0.0786(15) Uani 1 1 d . . . C47 C 0.0334(5) 0.2944(4) 0.2491(3) 0.112(2) Uani 1 1 d . . . H47 H -0.0204 0.3304 0.2416 0.134 Uiso 1 1 calc R . . C48 C 0.0585(7) 0.2206(6) 0.2088(2) 0.138(3) Uani 1 1 d . . . H48 H 0.0224 0.2082 0.1743 0.166 Uiso 1 1 calc R . . C49 C 0.1361(7) 0.1681(7) 0.2211(4) 0.161(4) Uani 1 1 d . . . H49 H 0.1525 0.1192 0.1946 0.193 Uiso 1 1 calc R . . C50 C 0.1896(6) 0.1848(6) 0.2702(4) 0.168(3) Uani 1 1 d . . . H50 H 0.2417 0.1471 0.2779 0.202 Uiso 1 1 calc R . . C51 C 0.1667(5) 0.2598(5) 0.3101(2) 0.127(2) Uani 1 1 d . . . H51 H 0.2050 0.2732 0.3440 0.152 Uiso 1 1 calc R . . C52 C 0.0508(4) 0.3642(4) 0.39061(19) 0.0635(13) Uani 1 1 d . . . C53 C -0.0062(4) 0.2814(4) 0.3942(2) 0.0830(15) Uani 1 1 d . . . H53 H -0.0389 0.2413 0.3627 0.100 Uiso 1 1 calc R . . C54 C -0.0167(4) 0.2556(4) 0.4423(2) 0.0894(17) Uani 1 1 d . . . H54 H -0.0558 0.1986 0.4435 0.107 Uiso 1 1 calc R . . C55 C 0.0299(4) 0.3131(5) 0.4882(2) 0.0861(17) Uani 1 1 d . . . H55 H 0.0239 0.2955 0.5211 0.103 Uiso 1 1 calc R . . C56 C 0.0852(4) 0.3960(5) 0.4862(2) 0.0952(17) Uani 1 1 d . . . H56 H 0.1159 0.4361 0.5181 0.114 Uiso 1 1 calc R . . C57 C 0.0972(4) 0.4229(4) 0.4372(2) 0.0904(16) Uani 1 1 d . . . H57 H 0.1363 0.4799 0.4362 0.108 Uiso 1 1 calc R . . C58 C 0.6047(4) 0.2595(4) 0.39687(17) 0.0581(12) Uani 1 1 d . . . C59 C 0.5325(4) 0.2048(4) 0.3553(2) 0.0647(13) Uani 1 1 d . . . C60 C 0.4554(4) 0.1260(4) 0.36512(18) 0.0972(16) Uani 1 1 d . . . H60A H 0.4131 0.0974 0.3319 0.146 Uiso 1 1 calc R . . H60B H 0.4130 0.1535 0.3911 0.146 Uiso 1 1 calc R . . H60C H 0.4914 0.0776 0.3785 0.146 Uiso 1 1 calc R . . C61 C 0.5276(4) 0.2240(4) 0.30425(19) 0.0858(17) Uani 1 1 d . . . H61 H 0.4779 0.1882 0.2777 0.103 Uiso 1 1 calc R . . C62 C 0.5909(5) 0.2919(5) 0.2907(2) 0.0867(18) Uani 1 1 d . . . C63 C 0.5849(5) 0.3101(5) 0.23341(18) 0.160(3) Uani 1 1 d . . . H63A H 0.5308 0.2668 0.2109 0.240 Uiso 1 1 calc R . . H63B H 0.6491 0.2995 0.2199 0.240 Uiso 1 1 calc R . . H63C H 0.5710 0.3754 0.2334 0.240 Uiso 1 1 calc R . . C64 C 0.6630(4) 0.3446(4) 0.3299(3) 0.0833(16) Uani 1 1 d . . . H64 H 0.7086 0.3909 0.3211 0.100 Uiso 1 1 calc R . . C65 C 0.6702(4) 0.3308(4) 0.3833(2) 0.0654(13) Uani 1 1 d . . . C66 C 0.7489(4) 0.3937(4) 0.42481(19) 0.0896(16) Uani 1 1 d . . . H66A H 0.7444 0.3763 0.4592 0.134 Uiso 1 1 calc R . . H66B H 0.7365 0.4599 0.4270 0.134 Uiso 1 1 calc R . . H66C H 0.8162 0.3852 0.4148 0.134 Uiso 1 1 calc R . . C67 C 0.6049(3) 0.3097(3) 0.50661(16) 0.0507(11) Uani 1 1 d . . . C68 C 0.5171(3) 0.3597(3) 0.51047(17) 0.0582(12) Uani 1 1 d . . . C69 C 0.4270(3) 0.3420(3) 0.46603(16) 0.0773(14) Uani 1 1 d . . . H69A H 0.4417 0.2951 0.4363 0.116 Uiso 1 1 calc R . . H69B H 0.4159 0.4012 0.4543 0.116 Uiso 1 1 calc R . . H69C H 0.3665 0.3185 0.4794 0.116 Uiso 1 1 calc R . . C70 C 0.5067(4) 0.4260(3) 0.5563(2) 0.0703(14) Uani 1 1 d . . . H70 H 0.4475 0.4574 0.5576 0.084 Uiso 1 1 calc R . . C71 C 0.5814(4) 0.4464(3) 0.5997(2) 0.0734(14) Uani 1 1 d . . . C72 C 0.5711(4) 0.5211(4) 0.65097(16) 0.1094(19) Uani 1 1 d . . . H72A H 0.5062 0.5468 0.6468 0.164 Uiso 1 1 calc R . . H72B H 0.6257 0.5724 0.6564 0.164 Uiso 1 1 calc R . . H72C H 0.5752 0.4904 0.6815 0.164 Uiso 1 1 calc R . . C73 C 0.6696(4) 0.3997(3) 0.59713(16) 0.0682(13) Uani 1 1 d . . . H73 H 0.7216 0.4139 0.6261 0.082 Uiso 1 1 calc R . . C74 C 0.6812(3) 0.3316(3) 0.55154(18) 0.0573(12) Uani 1 1 d . . . C75 C 0.7807(3) 0.2873(3) 0.55208(15) 0.0806(15) Uani 1 1 d . . . H75A H 0.7805 0.2423 0.5189 0.121 Uiso 1 1 calc R . . H75B H 0.7887 0.2543 0.5817 0.121 Uiso 1 1 calc R . . H75C H 0.8366 0.3369 0.5560 0.121 Uiso 1 1 calc R . . C76 C 0.6437(3) 0.1318(3) 0.45997(15) 0.0523(12) Uani 1 1 d . . . C77 C 0.6206(3) 0.0917(3) 0.50303(15) 0.0546(12) Uani 1 1 d . . . H77 H 0.5894 0.1270 0.5301 0.065 Uiso 1 1 calc R . . C78 C 0.6431(3) 0.0007(4) 0.50647(15) 0.0554(12) Uani 1 1 d . . . H78 H 0.6265 -0.0244 0.5360 0.066 Uiso 1 1 calc R . . C79 C 0.6909(3) -0.0568(3) 0.46671(15) 0.0482(11) Uani 1 1 d . . . C80 C 0.7153(3) -0.0188(3) 0.42210(14) 0.0442(11) Uani 1 1 d . . . C81 C 0.6911(3) 0.0736(3) 0.42038(14) 0.0498(11) Uani 1 1 d . . . H81 H 0.7072 0.0994 0.3910 0.060 Uiso 1 1 calc R . . C82 C 0.7124(3) -0.1502(4) 0.47657(16) 0.0635(13) Uani 1 1 d . . . H82 H 0.7195 -0.1545 0.5127 0.076 Uiso 1 1 calc R . . C83 C 0.7239(3) -0.2311(3) 0.44336(17) 0.0646(13) Uani 1 1 d . . . H83 H 0.7340 -0.2839 0.4593 0.078 Uiso 1 1 calc R . . C84 C 0.7229(3) -0.2482(3) 0.38592(17) 0.0489(11) Uani 1 1 d . . . C85 C 0.7387(3) -0.1794(3) 0.35391(16) 0.0484(11) Uani 1 1 d . . . C86 C 0.7740(3) -0.0698(3) 0.37709(14) 0.0473(11) Uani 1 1 d . . . C87 C 0.7705(4) -0.0151(3) 0.33064(15) 0.0494(11) Uani 1 1 d . . . C88 C 0.6847(4) 0.0008(3) 0.29706(17) 0.0650(13) Uani 1 1 d . . . H88 H 0.6189 -0.0226 0.3016 0.078 Uiso 1 1 calc R . . C89 C 0.7002(5) 0.0518(4) 0.25711(18) 0.0806(16) Uani 1 1 d . . . H89 H 0.6437 0.0631 0.2347 0.097 Uiso 1 1 calc R . . C90 C 0.7962(6) 0.0861(4) 0.24966(19) 0.0936(18) Uani 1 1 d . . . H90 H 0.8041 0.1203 0.2224 0.112 Uiso 1 1 calc R . . C91 C 0.8833(4) 0.0703(3) 0.2826(2) 0.0796(15) Uani 1 1 d . . . H91 H 0.9488 0.0929 0.2771 0.096 Uiso 1 1 calc R . . C92 C 0.8693(4) 0.0200(3) 0.32373(16) 0.0549(12) Uani 1 1 d . . . C93 C 0.9417(4) -0.0072(3) 0.36349(17) 0.0544(12) Uani 1 1 d . . . C94 C 1.0485(4) 0.0108(3) 0.37050(19) 0.0707(14) Uani 1 1 d . . . H94 H 1.0822 0.0448 0.3485 0.085 Uiso 1 1 calc R . . C95 C 1.1020(4) -0.0235(4) 0.4110(2) 0.0819(16) Uani 1 1 d . . . H95 H 1.1733 -0.0128 0.4164 0.098 Uiso 1 1 calc R . . C96 C 1.0526(4) -0.0730(4) 0.44336(18) 0.0751(15) Uani 1 1 d . . . H96 H 1.0906 -0.0952 0.4706 0.090 Uiso 1 1 calc R . . C97 C 0.9456(4) -0.0907(3) 0.43601(16) 0.0605(12) Uani 1 1 d . . . H97 H 0.9124 -0.1244 0.4583 0.073 Uiso 1 1 calc R . . C98 C 0.8898(3) -0.0579(3) 0.39542(16) 0.0459(11) Uani 1 1 d . . . C99 C 0.7355(3) -0.2103(3) 0.29853(16) 0.0529(12) Uani 1 1 d . . . H99 H 0.7479 -0.1651 0.2773 0.063 Uiso 1 1 calc R . . C100 C 0.7138(3) -0.3078(4) 0.27408(18) 0.0563(12) Uani 1 1 d . . . C101 C 0.6972(3) -0.3744(3) 0.3056(2) 0.0640(13) Uani 1 1 d . . . H101 H 0.6821 -0.4394 0.2901 0.077 Uiso 1 1 calc R . . C102 C 0.7029(3) -0.3441(4) 0.36020(18) 0.0609(12) Uani 1 1 d . . . H102 H 0.6928 -0.3903 0.3811 0.073 Uiso 1 1 calc R . . C103 C 0.6987(4) -0.2659(4) 0.18441(19) 0.0697(14) Uani 1 1 d . . . C104 C 0.6137(4) -0.2136(4) 0.18237(19) 0.0834(16) Uani 1 1 d . . . H104 H 0.5616 -0.2232 0.2033 0.100 Uiso 1 1 calc R . . C105 C 0.6075(5) -0.1481(4) 0.1492(3) 0.1030(19) Uani 1 1 d . . . H105 H 0.5500 -0.1144 0.1478 0.124 Uiso 1 1 calc R . . C106 C 0.6815(7) -0.1301(5) 0.1184(2) 0.123(2) Uani 1 1 d . . . H106 H 0.6763 -0.0847 0.0965 0.147 Uiso 1 1 calc R . . C107 C 0.7660(6) -0.1835(6) 0.1211(3) 0.127(2) Uani 1 1 d . . . H107 H 0.8182 -0.1734 0.1004 0.153 Uiso 1 1 calc R . . C108 C 0.7742(4) -0.2494(5) 0.1529(2) 0.0955(17) Uani 1 1 d . . . H108 H 0.8312 -0.2839 0.1536 0.115 Uiso 1 1 calc R . . C109 C 0.7223(4) -0.4308(4) 0.19116(18) 0.0688(13) Uani 1 1 d . . . C110 C 0.6521(4) -0.4786(4) 0.14964(19) 0.0751(14) Uani 1 1 d . . . H110 H 0.5949 -0.4491 0.1390 0.090 Uiso 1 1 calc R . . C111 C 0.6641(5) -0.5684(5) 0.12346(19) 0.0962(18) Uani 1 1 d . . . H111 H 0.6157 -0.6001 0.0950 0.115 Uiso 1 1 calc R . . C112 C 0.7470(6) -0.6116(5) 0.1390(3) 0.117(2) Uani 1 1 d . . . H112 H 0.7552 -0.6733 0.1211 0.141 Uiso 1 1 calc R . . C113 C 0.8180(5) -0.5662(5) 0.1802(3) 0.131(2) Uani 1 1 d . . . H113 H 0.8746 -0.5967 0.1906 0.157 Uiso 1 1 calc R . . C114 C 0.8061(4) -0.4737(4) 0.20701(19) 0.110(2) Uani 1 1 d . . . H114 H 0.8546 -0.4416 0.2353 0.132 Uiso 1 1 calc R . . N1 N 0.0630(3) 0.3880(3) 0.33997(14) 0.0791(12) Uani 1 1 d . . . N2 N 0.7081(3) -0.3349(3) 0.21737(15) 0.0724(11) 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 B1 0.071(4) 0.065(4) 0.061(4) 0.014(3) 0.003(3) -0.011(4) B2 0.037(3) 0.055(4) 0.061(3) 0.013(3) 0.005(2) 0.001(3) C1 0.072(4) 0.073(4) 0.052(3) 0.013(3) 0.008(3) -0.009(3) C2 0.071(4) 0.087(5) 0.060(3) 0.015(3) 0.008(3) -0.009(4) C3 0.085(4) 0.124(5) 0.086(4) 0.015(4) -0.011(3) -0.001(4) C4 0.084(4) 0.102(5) 0.092(4) 0.021(4) 0.020(3) 0.021(4) C5 0.100(5) 0.092(5) 0.088(4) 0.010(4) 0.023(4) 0.011(5) C6 0.139(5) 0.106(5) 0.192(6) 0.023(5) 0.046(5) 0.049(5) C7 0.105(5) 0.071(5) 0.089(4) -0.001(3) 0.034(4) -0.010(4) C8 0.080(4) 0.074(4) 0.062(3) 0.007(3) 0.013(3) -0.003(4) C9 0.106(4) 0.108(5) 0.080(3) 0.003(3) 0.001(3) -0.008(4) C10 0.081(4) 0.074(4) 0.045(3) 0.010(3) 0.007(3) 0.002(3) C11 0.101(5) 0.075(4) 0.075(3) 0.020(3) 0.026(3) -0.010(4) C12 0.092(4) 0.125(5) 0.126(4) 0.040(4) 0.027(4) -0.008(4) C13 0.142(6) 0.079(5) 0.079(4) 0.027(3) 0.010(4) -0.023(5) C14 0.131(6) 0.087(5) 0.090(4) 0.030(4) 0.005(5) 0.010(5) C15 0.224(7) 0.097(5) 0.153(5) 0.070(5) -0.019(5) 0.015(5) C16 0.109(5) 0.106(5) 0.069(3) 0.034(4) -0.006(3) 0.007(4) C17 0.093(5) 0.095(5) 0.057(3) 0.017(3) 0.002(3) 0.011(4) C18 0.081(4) 0.140(6) 0.116(4) 0.054(4) 0.007(3) 0.004(4) C19 0.071(3) 0.062(4) 0.054(3) 0.017(3) 0.001(2) 0.007(3) C20 0.091(4) 0.078(4) 0.064(3) 0.020(3) -0.001(3) 0.028(3) C21 0.089(4) 0.076(4) 0.059(3) 0.014(3) 0.005(3) 0.035(3) C22 0.058(3) 0.056(3) 0.055(3) 0.014(3) 0.000(2) 0.014(3) C23 0.053(3) 0.055(3) 0.047(3) 0.015(2) 0.007(2) 0.010(3) C24 0.059(3) 0.059(3) 0.061(3) 0.016(3) 0.004(2) 0.017(3) C25 0.066(3) 0.067(4) 0.059(3) 0.010(3) 0.007(3) 0.026(3) C26 0.060(3) 0.070(4) 0.052(3) -0.001(3) 0.011(2) 0.020(3) C27 0.046(3) 0.059(4) 0.046(3) 0.002(2) 0.007(2) 0.008(3) C28 0.050(3) 0.071(4) 0.043(2) 0.012(3) 0.007(2) 0.008(3) C29 0.056(3) 0.065(4) 0.056(3) 0.021(3) 0.015(3) 0.020(3) C30 0.099(5) 0.090(5) 0.067(4) 0.041(3) 0.037(3) 0.043(4) C31 0.176(6) 0.089(5) 0.078(4) 0.029(4) 0.053(4) 0.060(5) C32 0.279(10) 0.122(6) 0.115(5) 0.057(5) 0.103(7) 0.118(9) C33 0.290(15) 0.227(13) 0.150(9) 0.101(8) 0.140(11) 0.185(14) C34 0.192(9) 0.270(12) 0.155(8) 0.136(8) 0.121(7) 0.185(10) C35 0.097(6) 0.155(7) 0.113(5) 0.097(5) 0.062(5) 0.074(6) C36 0.058(5) 0.164(7) 0.119(5) 0.093(5) 0.032(4) 0.034(5) C37 0.039(4) 0.265(12) 0.165(8) 0.156(7) 0.027(6) 0.036(7) C38 0.077(6) 0.269(14) 0.154(8) 0.117(8) -0.014(6) -0.013(8) C39 0.076(4) 0.149(6) 0.106(4) 0.050(4) -0.019(4) -0.035(5) C40 0.056(4) 0.113(5) 0.083(4) 0.035(4) -0.002(3) -0.008(4) C41 0.056(4) 0.102(5) 0.068(3) 0.050(3) 0.016(3) 0.019(4) C42 0.073(3) 0.061(4) 0.057(3) 0.012(3) 0.017(2) 0.013(3) C43 0.076(3) 0.067(4) 0.046(3) 0.013(3) 0.015(2) 0.004(3) C44 0.066(3) 0.078(4) 0.059(3) 0.016(3) 0.017(2) -0.005(3) C45 0.051(3) 0.071(4) 0.053(3) -0.002(3) 0.008(2) 0.008(3) C46 0.098(4) 0.078(4) 0.065(4) 0.022(3) 0.019(3) 0.007(4) C47 0.185(6) 0.076(5) 0.077(4) 0.017(4) 0.019(4) 0.019(4) C48 0.225(9) 0.105(6) 0.068(4) -0.012(4) 0.028(5) -0.024(6) C49 0.186(9) 0.159(8) 0.147(8) 0.007(7) 0.074(7) 0.060(7) C50 0.159(7) 0.204(9) 0.137(6) -0.015(7) 0.038(6) 0.080(6) C51 0.111(5) 0.168(7) 0.106(5) 0.011(5) 0.033(4) 0.049(5) C52 0.078(4) 0.062(4) 0.054(3) 0.013(3) 0.020(3) 0.005(3) C53 0.109(4) 0.069(4) 0.071(4) 0.011(3) 0.029(3) -0.005(4) C54 0.120(5) 0.073(4) 0.077(4) 0.015(4) 0.030(4) -0.006(4) C55 0.101(4) 0.077(5) 0.093(5) 0.042(4) 0.023(4) 0.012(4) C56 0.128(5) 0.088(5) 0.063(4) 0.011(4) 0.002(3) -0.005(4) C57 0.118(4) 0.071(4) 0.078(4) 0.017(4) 0.011(3) -0.026(3) C58 0.058(3) 0.052(4) 0.064(3) 0.005(3) 0.003(3) 0.019(3) C59 0.078(4) 0.053(4) 0.065(3) 0.017(3) 0.006(3) 0.016(3) C60 0.090(4) 0.092(5) 0.099(4) 0.018(3) -0.017(3) -0.009(4) C61 0.119(5) 0.083(5) 0.057(4) 0.016(3) 0.002(3) 0.025(4) C62 0.123(5) 0.077(5) 0.068(4) 0.024(4) 0.013(4) 0.030(4) C63 0.261(8) 0.167(7) 0.068(4) 0.060(4) 0.017(4) 0.040(6) C64 0.105(5) 0.075(4) 0.090(4) 0.042(4) 0.038(4) 0.033(4) C65 0.064(4) 0.053(4) 0.084(4) 0.020(3) 0.016(3) 0.017(3) C66 0.086(4) 0.072(4) 0.118(4) 0.034(4) 0.021(3) 0.005(3) C67 0.050(3) 0.042(3) 0.063(3) 0.015(2) 0.008(2) 0.013(3) C68 0.065(3) 0.056(3) 0.060(3) 0.024(3) 0.009(3) 0.013(3) C69 0.072(3) 0.086(4) 0.084(3) 0.029(3) 0.016(3) 0.030(3) C70 0.073(4) 0.070(4) 0.074(3) 0.018(3) 0.022(3) 0.022(3) C71 0.101(4) 0.059(4) 0.069(3) 0.016(3) 0.029(3) 0.025(3) C72 0.170(5) 0.086(4) 0.075(3) -0.002(3) 0.033(3) 0.050(4) C73 0.081(4) 0.066(4) 0.057(3) 0.012(3) 0.004(3) 0.016(3) C74 0.049(3) 0.058(3) 0.068(3) 0.015(3) 0.011(3) 0.011(3) C75 0.072(3) 0.087(4) 0.078(3) 0.008(3) -0.001(3) 0.013(3) C76 0.060(3) 0.054(3) 0.049(3) 0.016(2) 0.009(2) 0.017(3) C77 0.054(3) 0.056(4) 0.055(3) 0.008(3) 0.014(2) 0.013(3) C78 0.051(3) 0.068(4) 0.048(3) 0.012(3) 0.011(2) 0.002(3) C79 0.053(3) 0.045(3) 0.046(3) 0.010(2) 0.003(2) -0.001(2) C80 0.046(3) 0.037(3) 0.049(3) 0.008(2) 0.006(2) 0.008(2) C81 0.047(3) 0.059(4) 0.042(2) 0.010(2) 0.002(2) -0.001(3) C82 0.088(4) 0.059(4) 0.051(3) 0.024(3) 0.012(2) 0.012(3) C83 0.087(3) 0.057(4) 0.056(3) 0.019(3) 0.012(2) 0.024(3) C84 0.050(3) 0.037(3) 0.060(3) 0.012(3) 0.005(2) 0.004(2) C85 0.043(3) 0.042(3) 0.056(3) -0.002(3) 0.002(2) 0.009(2) C86 0.044(3) 0.060(3) 0.040(2) 0.012(2) 0.007(2) 0.011(2) C87 0.055(3) 0.044(3) 0.048(3) 0.003(2) 0.008(2) 0.007(3) C88 0.077(4) 0.064(4) 0.057(3) 0.015(3) 0.010(3) 0.015(3) C89 0.102(5) 0.087(4) 0.064(3) 0.033(3) 0.019(3) 0.025(4) C90 0.141(5) 0.086(5) 0.068(4) 0.038(3) 0.028(4) 0.026(5) C91 0.098(4) 0.061(4) 0.084(4) 0.021(3) 0.028(3) 0.001(3) C92 0.076(4) 0.038(3) 0.052(3) 0.009(2) 0.017(3) -0.001(3) C93 0.055(3) 0.044(3) 0.058(3) -0.001(2) -0.002(3) 0.003(3) C94 0.058(4) 0.068(4) 0.076(3) 0.001(3) 0.000(3) -0.011(3) C95 0.048(3) 0.090(5) 0.091(4) -0.013(3) 0.002(3) -0.006(3) C96 0.057(4) 0.091(4) 0.070(3) -0.001(3) -0.002(3) 0.018(3) C97 0.059(3) 0.062(3) 0.060(3) 0.006(3) 0.008(2) 0.011(3) C98 0.055(3) 0.035(3) 0.046(3) 0.006(2) 0.003(2) 0.002(2) C99 0.052(3) 0.048(3) 0.057(3) 0.004(3) 0.009(2) 0.004(3) C100 0.048(3) 0.065(4) 0.052(3) 0.000(3) 0.004(2) 0.011(3) C101 0.059(3) 0.047(4) 0.083(4) 0.008(3) 0.003(3) 0.010(3) C102 0.068(3) 0.051(4) 0.062(3) 0.006(3) 0.008(2) 0.009(3) C103 0.068(4) 0.074(4) 0.058(3) 0.001(3) 0.000(3) -0.010(4) C104 0.065(4) 0.102(5) 0.081(4) 0.023(4) -0.005(3) 0.006(4) C105 0.116(5) 0.082(5) 0.105(5) 0.030(4) -0.029(4) 0.005(4) C106 0.180(8) 0.100(6) 0.085(4) 0.033(4) 0.018(5) -0.033(6) C107 0.162(7) 0.100(6) 0.123(6) 0.016(5) 0.055(5) 0.000(5) C108 0.093(4) 0.081(5) 0.111(4) 0.016(4) 0.021(4) -0.006(4) C109 0.071(4) 0.065(4) 0.063(3) -0.006(3) 0.005(3) 0.013(3) C110 0.079(4) 0.073(4) 0.063(3) 0.002(3) -0.004(3) -0.001(3) C111 0.142(6) 0.071(5) 0.062(3) -0.012(3) -0.001(3) 0.009(4) C112 0.175(7) 0.100(6) 0.081(4) 0.003(4) 0.028(4) 0.056(6) C113 0.138(6) 0.141(7) 0.105(5) -0.012(5) -0.003(4) 0.078(5) C114 0.100(4) 0.118(5) 0.094(4) -0.031(4) -0.017(3) 0.062(4) N1 0.132(4) 0.050(3) 0.060(3) 0.011(2) 0.033(2) 0.010(3) N2 0.083(3) 0.070(3) 0.058(3) 0.002(3) -0.001(2) 0.009(3) _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 B1 C19 1.574(6) . ? B1 C1 1.580(7) . ? B1 C10 1.606(6) . ? B2 C67 1.557(6) . ? B2 C76 1.558(6) . ? B2 C58 1.583(6) . ? C1 C8 1.404(6) . ? C1 C2 1.410(6) . ? C2 C4 1.379(6) . ? C2 C3 1.523(6) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.356(6) . ? C4 H4 0.9300 . ? C5 C7 1.387(6) . ? C5 C6 1.516(7) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.382(6) . ? C7 H7 0.9300 . ? C8 C9 1.539(6) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C17 1.408(6) . ? C10 C11 1.417(6) . ? C11 C13 1.409(6) . ? C11 C12 1.494(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.372(7) . ? C13 H13 0.9300 . ? C14 C16 1.346(7) . ? C14 C15 1.518(7) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.393(6) . ? C16 H16 0.9300 . ? C17 C18 1.511(6) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.396(5) . ? C19 C24 1.414(5) . ? C20 C21 1.384(5) . ? C20 H20 0.9300 . ? C21 C22 1.404(5) . ? C21 H21 0.9300 . ? C22 C23 1.393(5) . ? C22 C25 1.450(5) . ? C23 C24 1.405(4) . ? C23 C29 1.542(5) . ? C24 H24 0.9300 . ? C25 C26 1.332(5) . ? C25 H25 0.9300 . ? C26 C27 1.460(5) . ? C26 H26 0.9300 . ? C27 C45 1.396(5) . ? C27 C28 1.400(5) . ? C28 C42 1.389(5) . ? C28 C29 1.546(5) . ? C29 C30 1.547(6) . ? C29 C41 1.549(6) . ? C30 C31 1.372(7) . ? C30 C35 1.395(7) . ? C31 C32 1.404(8) . ? C31 H31 0.9300 . ? C32 C33 1.382(13) . ? C32 H32 0.9300 . ? C33 C34 1.373(14) . ? C33 H33 0.9300 . ? C34 C35 1.406(9) . ? C34 H34 0.9300 . ? C35 C36 1.454(8) . ? C36 C41 1.406(6) . ? C36 C37 1.437(9) . ? C37 C38 1.371(10) . ? C37 H37 0.9300 . ? C38 C39 1.328(9) . ? C38 H38 0.9300 . ? C39 C40 1.383(7) . ? C39 H39 0.9300 . ? C40 C41 1.380(6) . ? C40 H40 0.9300 . ? C42 C43 1.396(5) . ? C42 H42 0.9300 . ? C43 N1 1.383(5) . ? C43 C44 1.397(5) . ? C44 C45 1.370(5) . ? C44 H44 0.9300 . ? C45 H45 0.9300 . ? C46 C47 1.358(6) . ? C46 C51 1.362(6) . ? C46 N1 1.437(5) . ? C47 C48 1.412(7) . ? C47 H47 0.9300 . ? C48 C49 1.357(8) . ? C48 H48 0.9300 . ? C49 C50 1.337(8) . ? C49 H49 0.9300 . ? C50 C51 1.405(8) . ? C50 H50 0.9300 . ? C51 H51 0.9300 . ? C52 C53 1.365(6) . ? C52 C57 1.367(6) . ? C52 N1 1.417(5) . ? C53 C54 1.361(6) . ? C53 H53 0.9300 . ? C54 C55 1.347(6) . ? C54 H54 0.9300 . ? C55 C56 1.345(6) . ? C55 H55 0.9300 . ? C56 C57 1.393(6) . ? C56 H56 0.9300 . ? C57 H57 0.9300 . ? C58 C65 1.394(6) . ? C58 C59 1.407(6) . ? C59 C61 1.375(6) . ? C59 C60 1.524(6) . ? C60 H60A 0.9600 . ? C60 H60B 0.9600 . ? C60 H60C 0.9600 . ? C61 C62 1.340(6) . ? C61 H61 0.9300 . ? C62 C64 1.363(6) . ? C62 C63 1.526(6) . ? C63 H63A 0.9600 . ? C63 H63B 0.9600 . ? C63 H63C 0.9600 . ? C64 C65 1.404(6) . ? C64 H64 0.9300 . ? C65 C66 1.499(6) . ? C66 H66A 0.9600 . ? C66 H66B 0.9600 . ? C66 H66C 0.9600 . ? C67 C68 1.409(5) . ? C67 C74 1.408(5) . ? C68 C70 1.383(5) . ? C68 C69 1.518(5) . ? C69 H69A 0.9600 . ? C69 H69B 0.9600 . ? C69 H69C 0.9600 . ? C70 C71 1.369(6) . ? C70 H70 0.9300 . ? C71 C73 1.385(5) . ? C71 C72 1.547(5) . ? C72 H72A 0.9600 . ? C72 H72B 0.9600 . ? C72 H72C 0.9600 . ? C73 C74 1.397(5) . ? C73 H73 0.9300 . ? C74 C75 1.499(5) . ? C75 H75A 0.9600 . ? C75 H75B 0.9600 . ? C75 H75C 0.9600 . ? C76 C77 1.379(5) . ? C76 C81 1.415(5) . ? C77 C78 1.366(5) . ? C77 H77 0.9300 . ? C78 C79 1.415(5) . ? C78 H78 0.9300 . ? C79 C80 1.403(5) . ? C79 C82 1.441(5) . ? C80 C81 1.383(5) . ? C80 C86 1.554(5) . ? C81 H81 0.9300 . ? C82 C83 1.323(5) . ? C82 H82 0.9300 . ? C83 C84 1.437(5) . ? C83 H83 0.9300 . ? C84 C102 1.387(5) . ? C84 C85 1.403(5) . ? C85 C99 1.392(5) . ? C85 C86 1.570(5) . ? C86 C98 1.531(5) . ? C86 C87 1.532(5) . ? C87 C92 1.397(5) . ? C87 C88 1.400(5) . ? C88 C89 1.379(5) . ? C88 H88 0.9300 . ? C89 C90 1.363(6) . ? C89 H89 0.9300 . ? C90 C91 1.404(6) . ? C90 H90 0.9300 . ? C91 C92 1.395(5) . ? C91 H91 0.9300 . ? C92 C93 1.442(5) . ? C93 C98 1.381(5) . ? C93 C94 1.395(5) . ? C94 C95 1.373(5) . ? C94 H94 0.9300 . ? C95 C96 1.362(6) . ? C95 H95 0.9300 . ? C96 C97 1.397(5) . ? C96 H96 0.9300 . ? C97 C98 1.378(5) . ? C97 H97 0.9300 . ? C99 C100 1.400(5) . ? C99 H99 0.9300 . ? C100 C101 1.369(5) . ? C100 N2 1.417(5) . ? C101 C102 1.370(5) . ? C101 H101 0.9300 . ? C102 H102 0.9300 . ? C103 C108 1.375(6) . ? C103 C104 1.395(6) . ? C103 N2 1.410(5) . ? C104 C105 1.370(6) . ? C104 H104 0.9300 . ? C105 C106 1.354(7) . ? C105 H105 0.9300 . ? C106 C107 1.401(8) . ? C106 H106 0.9300 . ? C107 C108 1.352(7) . ? C107 H107 0.9300 . ? C108 H108 0.9300 . ? C109 C110 1.360(5) . ? C109 C114 1.362(5) . ? C109 N2 1.436(5) . ? C110 C111 1.354(6) . ? C110 H110 0.9300 . ? C111 C112 1.353(6) . ? C111 H111 0.9300 . ? C112 C113 1.351(7) . ? C112 H112 0.9300 . ? C113 C114 1.393(7) . ? C113 H113 0.9300 . ? C114 H114 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 B1 C1 120.4(4) . . ? C19 B1 C10 117.8(4) . . ? C1 B1 C10 121.8(4) . . ? C67 B2 C76 120.0(4) . . ? C67 B2 C58 122.6(4) . . ? C76 B2 C58 117.4(4) . . ? C8 C1 C2 116.6(5) . . ? C8 C1 B1 120.3(5) . . ? C2 C1 B1 123.1(5) . . ? C4 C2 C1 120.3(5) . . ? C4 C2 C3 117.9(5) . . ? C1 C2 C3 121.7(5) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C2 123.6(5) . . ? C5 C4 H4 118.2 . . ? C2 C4 H4 118.2 . . ? C4 C5 C7 116.3(6) . . ? C4 C5 C6 122.2(6) . . ? C7 C5 C6 121.5(6) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C5 122.8(5) . . ? C8 C7 H7 118.6 . . ? C5 C7 H7 118.6 . . ? C7 C8 C1 120.3(5) . . ? C7 C8 C9 117.2(5) . . ? C1 C8 C9 122.5(5) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C17 C10 C11 118.7(5) . . ? C17 C10 B1 121.9(5) . . ? C11 C10 B1 119.2(5) . . ? C13 C11 C10 117.4(5) . . ? C13 C11 C12 119.9(6) . . ? C10 C11 C12 122.7(5) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C11 123.1(6) . . ? C14 C13 H13 118.4 . . ? C11 C13 H13 118.4 . . ? C16 C14 C13 118.6(6) . . ? C16 C14 C15 123.0(7) . . ? C13 C14 C15 118.4(7) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 C17 122.0(6) . . ? C14 C16 H16 119.0 . . ? C17 C16 H16 119.0 . . ? C16 C17 C10 120.0(5) . . ? C16 C17 C18 116.8(5) . . ? C10 C17 C18 123.0(5) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 115.6(4) . . ? C20 C19 B1 122.1(4) . . ? C24 C19 B1 122.3(4) . . ? C21 C20 C19 121.4(4) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C20 C21 C22 121.3(4) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C23 C22 C21 120.0(4) . . ? C23 C22 C25 125.8(4) . . ? C21 C22 C25 114.2(4) . . ? C22 C23 C24 116.7(4) . . ? C22 C23 C29 124.0(4) . . ? C24 C23 C29 118.8(4) . . ? C23 C24 C19 124.8(4) . . ? C23 C24 H24 117.6 . . ? C19 C24 H24 117.6 . . ? C26 C25 C22 131.2(4) . . ? C26 C25 H25 114.4 . . ? C22 C25 H25 114.4 . . ? C25 C26 C27 130.2(4) . . ? C25 C26 H26 114.9 . . ? C27 C26 H26 114.9 . . ? C45 C27 C28 117.7(4) . . ? C45 C27 C26 115.4(4) . . ? C28 C27 C26 126.9(4) . . ? C42 C28 C27 117.4(4) . . ? C42 C28 C29 118.6(4) . . ? C27 C28 C29 123.5(4) . . ? C23 C29 C28 118.9(3) . . ? C23 C29 C30 109.8(3) . . ? C28 C29 C30 110.2(4) . . ? C23 C29 C41 108.3(3) . . ? C28 C29 C41 108.0(3) . . ? C30 C29 C41 99.9(4) . . ? C31 C30 C35 122.4(6) . . ? C31 C30 C29 127.2(6) . . ? C35 C30 C29 110.4(6) . . ? C30 C31 C32 118.3(7) . . ? C30 C31 H31 120.8 . . ? C32 C31 H31 120.8 . . ? C33 C32 C31 119.6(10) . . ? C33 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? C34 C33 C32 122.1(11) . . ? C34 C33 H33 119.0 . . ? C32 C33 H33 119.0 . . ? C33 C34 C35 118.8(11) . . ? C33 C34 H34 120.6 . . ? C35 C34 H34 120.6 . . ? C30 C35 C34 118.8(8) . . ? C30 C35 C36 110.4(6) . . ? C34 C35 C36 130.9(8) . . ? C41 C36 C37 119.5(7) . . ? C41 C36 C35 107.8(6) . . ? C37 C36 C35 132.7(7) . . ? C38 C37 C36 118.7(9) . . ? C38 C37 H37 120.7 . . ? C36 C37 H37 120.7 . . ? C39 C38 C37 121.1(10) . . ? C39 C38 H38 119.4 . . ? C37 C38 H38 119.4 . . ? C38 C39 C40 121.6(8) . . ? C38 C39 H39 119.2 . . ? C40 C39 H39 119.2 . . ? C41 C40 C39 120.8(6) . . ? C41 C40 H40 119.6 . . ? C39 C40 H40 119.6 . . ? C40 C41 C36 118.1(6) . . ? C40 C41 C29 130.5(5) . . ? C36 C41 C29 111.4(6) . . ? C28 C42 C43 124.9(4) . . ? C28 C42 H42 117.6 . . ? C43 C42 H42 117.6 . . ? N1 C43 C42 120.8(4) . . ? N1 C43 C44 122.4(4) . . ? C42 C43 C44 116.7(5) . . ? C45 C44 C43 119.0(4) . . ? C45 C44 H44 120.5 . . ? C43 C44 H44 120.5 . . ? C44 C45 C27 124.1(4) . . ? C44 C45 H45 117.9 . . ? C27 C45 H45 117.9 . . ? C47 C46 C51 120.3(6) . . ? C47 C46 N1 119.8(6) . . ? C51 C46 N1 120.0(5) . . ? C46 C47 C48 119.7(6) . . ? C46 C47 H47 120.1 . . ? C48 C47 H47 120.1 . . ? C49 C48 C47 118.9(7) . . ? C49 C48 H48 120.5 . . ? C47 C48 H48 120.5 . . ? C50 C49 C48 121.8(9) . . ? C50 C49 H49 119.1 . . ? C48 C49 H49 119.1 . . ? C49 C50 C51 119.5(8) . . ? C49 C50 H50 120.2 . . ? C51 C50 H50 120.2 . . ? C46 C51 C50 119.8(6) . . ? C46 C51 H51 120.1 . . ? C50 C51 H51 120.1 . . ? C53 C52 C57 118.3(4) . . ? C53 C52 N1 121.0(5) . . ? C57 C52 N1 120.7(5) . . ? C54 C53 C52 122.0(5) . . ? C54 C53 H53 119.0 . . ? C52 C53 H53 119.0 . . ? C55 C54 C53 119.6(5) . . ? C55 C54 H54 120.2 . . ? C53 C54 H54 120.2 . . ? C56 C55 C54 119.9(5) . . ? C56 C55 H55 120.1 . . ? C54 C55 H55 120.1 . . ? C55 C56 C57 121.1(5) . . ? C55 C56 H56 119.4 . . ? C57 C56 H56 119.4 . . ? C52 C57 C56 119.1(5) . . ? C52 C57 H57 120.5 . . ? C56 C57 H57 120.5 . . ? C65 C58 C59 117.1(4) . . ? C65 C58 B2 121.6(4) . . ? C59 C58 B2 121.1(5) . . ? C61 C59 C58 120.0(5) . . ? C61 C59 C60 117.8(5) . . ? C58 C59 C60 122.2(4) . . ? C59 C60 H60A 109.5 . . ? C59 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C59 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? C62 C61 C59 123.3(5) . . ? C62 C61 H61 118.3 . . ? C59 C61 H61 118.3 . . ? C61 C62 C64 117.9(5) . . ? C61 C62 C63 122.1(6) . . ? C64 C62 C63 120.0(6) . . ? C62 C63 H63A 109.5 . . ? C62 C63 H63B 109.5 . . ? H63A C63 H63B 109.5 . . ? C62 C63 H63C 109.5 . . ? H63A C63 H63C 109.5 . . ? H63B C63 H63C 109.5 . . ? C62 C64 C65 121.8(5) . . ? C62 C64 H64 119.1 . . ? C65 C64 H64 119.1 . . ? C58 C65 C64 119.9(5) . . ? C58 C65 C66 121.1(5) . . ? C64 C65 C66 119.0(5) . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C68 C67 C74 116.4(4) . . ? C68 C67 B2 121.6(4) . . ? C74 C67 B2 122.0(4) . . ? C70 C68 C67 121.5(4) . . ? C70 C68 C69 115.9(4) . . ? C67 C68 C69 122.6(4) . . ? C68 C69 H69A 109.5 . . ? C68 C69 H69B 109.5 . . ? H69A C69 H69B 109.5 . . ? C68 C69 H69C 109.5 . . ? H69A C69 H69C 109.5 . . ? H69B C69 H69C 109.5 . . ? C71 C70 C68 121.5(4) . . ? C71 C70 H70 119.2 . . ? C68 C70 H70 119.2 . . ? C70 C71 C73 118.7(4) . . ? C70 C71 C72 122.1(5) . . ? C73 C71 C72 119.2(5) . . ? C71 C72 H72A 109.5 . . ? C71 C72 H72B 109.5 . . ? H72A C72 H72B 109.5 . . ? C71 C72 H72C 109.5 . . ? H72A C72 H72C 109.5 . . ? H72B C72 H72C 109.5 . . ? C71 C73 C74 120.7(4) . . ? C71 C73 H73 119.6 . . ? C74 C73 H73 119.6 . . ? C73 C74 C67 121.2(4) . . ? C73 C74 C75 116.6(4) . . ? C67 C74 C75 122.1(4) . . ? C74 C75 H75A 109.5 . . ? C74 C75 H75B 109.5 . . ? H75A C75 H75B 109.5 . . ? C74 C75 H75C 109.5 . . ? H75A C75 H75C 109.5 . . ? H75B C75 H75C 109.5 . . ? C77 C76 C81 116.3(4) . . ? C77 C76 B2 121.3(4) . . ? C81 C76 B2 122.3(4) . . ? C78 C77 C76 120.9(4) . . ? C78 C77 H77 119.6 . . ? C76 C77 H77 119.6 . . ? C77 C78 C79 122.3(4) . . ? C77 C78 H78 118.8 . . ? C79 C78 H78 118.8 . . ? C80 C79 C78 118.6(4) . . ? C80 C79 C82 125.4(4) . . ? C78 C79 C82 116.0(4) . . ? C81 C80 C79 117.0(3) . . ? C81 C80 C86 118.1(3) . . ? C79 C80 C86 124.8(4) . . ? C80 C81 C76 124.9(4) . . ? C80 C81 H81 117.6 . . ? C76 C81 H81 117.6 . . ? C83 C82 C79 131.5(4) . . ? C83 C82 H82 114.3 . . ? C79 C82 H82 114.3 . . ? C82 C83 C84 128.7(4) . . ? C82 C83 H83 115.6 . . ? C84 C83 H83 115.6 . . ? C102 C84 C85 117.7(4) . . ? C102 C84 C83 115.0(4) . . ? C85 C84 C83 127.3(4) . . ? C99 C85 C84 118.9(4) . . ? C99 C85 C86 116.6(4) . . ? C84 C85 C86 124.0(4) . . ? C98 C86 C87 100.3(3) . . ? C98 C86 C80 110.9(3) . . ? C87 C86 C80 109.8(3) . . ? C98 C86 C85 108.7(3) . . ? C87 C86 C85 109.1(3) . . ? C80 C86 C85 116.7(3) . . ? C92 C87 C88 120.7(4) . . ? C92 C87 C86 110.8(4) . . ? C88 C87 C86 128.6(4) . . ? C89 C88 C87 118.5(4) . . ? C89 C88 H88 120.8 . . ? C87 C88 H88 120.8 . . ? C90 C89 C88 121.5(5) . . ? C90 C89 H89 119.2 . . ? C88 C89 H89 119.2 . . ? C89 C90 C91 120.9(5) . . ? C89 C90 H90 119.5 . . ? C91 C90 H90 119.5 . . ? C92 C91 C90 118.5(5) . . ? C92 C91 H91 120.8 . . ? C90 C91 H91 120.8 . . ? C91 C92 C87 119.9(4) . . ? C91 C92 C93 131.6(5) . . ? C87 C92 C93 108.5(4) . . ? C98 C93 C94 122.3(4) . . ? C98 C93 C92 109.7(4) . . ? C94 C93 C92 128.0(5) . . ? C95 C94 C93 117.6(4) . . ? C95 C94 H94 121.2 . . ? C93 C94 H94 121.2 . . ? C96 C95 C94 121.3(5) . . ? C96 C95 H95 119.4 . . ? C94 C95 H95 119.4 . . ? C95 C96 C97 120.7(4) . . ? C95 C96 H96 119.6 . . ? C97 C96 H96 119.6 . . ? C98 C97 C96 119.4(4) . . ? C98 C97 H97 120.3 . . ? C96 C97 H97 120.3 . . ? C97 C98 C93 118.7(4) . . ? C97 C98 C86 130.5(4) . . ? C93 C98 C86 110.7(4) . . ? C85 C99 C100 121.6(4) . . ? C85 C99 H99 119.2 . . ? C100 C99 H99 119.2 . . ? C101 C100 C99 119.1(4) . . ? C101 C100 N2 121.6(5) . . ? C99 C100 N2 119.3(5) . . ? C100 C101 C102 119.2(4) . . ? C100 C101 H101 120.4 . . ? C102 C101 H101 120.4 . . ? C101 C102 C84 123.5(4) . . ? C101 C102 H102 118.3 . . ? C84 C102 H102 118.3 . . ? C108 C103 C104 118.5(5) . . ? C108 C103 N2 119.9(6) . . ? C104 C103 N2 121.6(5) . . ? C105 C104 C103 119.3(5) . . ? C105 C104 H104 120.3 . . ? C103 C104 H104 120.3 . . ? C106 C105 C104 123.1(6) . . ? C106 C105 H105 118.5 . . ? C104 C105 H105 118.5 . . ? C105 C106 C107 116.5(7) . . ? C105 C106 H106 121.8 . . ? C107 C106 H106 121.8 . . ? C108 C107 C106 122.1(7) . . ? C108 C107 H107 118.9 . . ? C106 C107 H107 118.9 . . ? C107 C108 C103 120.5(6) . . ? C107 C108 H108 119.7 . . ? C103 C108 H108 119.7 . . ? C110 C109 C114 119.7(5) . . ? C110 C109 N2 119.7(5) . . ? C114 C109 N2 120.6(5) . . ? C111 C110 C109 121.1(5) . . ? C111 C110 H110 119.4 . . ? C109 C110 H110 119.4 . . ? C110 C111 C112 119.6(6) . . ? C110 C111 H111 120.2 . . ? C112 C111 H111 120.2 . . ? C113 C112 C111 120.8(6) . . ? C113 C112 H112 119.6 . . ? C111 C112 H112 119.6 . . ? C112 C113 C114 119.7(6) . . ? C112 C113 H113 120.2 . . ? C114 C113 H113 120.2 . . ? C109 C114 C113 119.1(5) . . ? C109 C114 H114 120.5 . . ? C113 C114 H114 120.5 . . ? C43 N1 C52 122.5(4) . . ? C43 N1 C46 120.6(4) . . ? C52 N1 C46 116.9(4) . . ? C103 N2 C100 120.9(4) . . ? C103 N2 C109 116.7(4) . . ? C100 N2 C109 122.1(4) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.171 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.041 data_a12973 _database_code_depnum_ccdc_archive 'CCDC 880010' #TrackingRef '11064_web_deposit_cif_file_1_Chien-TienChen_1336029966.a12973.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H39 Cl2 N' _chemical_formula_sum 'C54 H39 Cl2 N' _chemical_formula_weight 772.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7030(12) _cell_length_b 13.3547(15) _cell_length_c 14.8791(13) _cell_angle_alpha 92.180(3) _cell_angle_beta 90.261(3) _cell_angle_gamma 109.366(3) _cell_volume 2004.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9183 _exptl_absorpt_correction_T_max 0.9346 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15827 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 24.99 _reflns_number_total 6844 _reflns_number_gt 5584 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0748P)^2^+0.5778P] 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 6844 _refine_ls_number_parameters 514 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1372 _refine_ls_wR_factor_gt 0.1235 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 0.6744(2) 1.15305(16) 0.36326(14) 0.0412(5) Uani 1 1 d . . . C2 C 0.6440(2) 1.19706(19) 0.28682(17) 0.0552(6) Uani 1 1 d . . . H2 H 0.6972 1.2035 0.2350 0.066 Uiso 1 1 calc R . . C3 C 0.5349(3) 1.2319(2) 0.2866(2) 0.0733(9) Uani 1 1 d . . . H3 H 0.5133 1.2615 0.2342 0.088 Uiso 1 1 calc R . . C4 C 0.4586(3) 1.2237(2) 0.3612(3) 0.0772(9) Uani 1 1 d . . . H4 H 0.3851 1.2485 0.3606 0.093 Uiso 1 1 calc R . . C5 C 0.4880(3) 1.1797(3) 0.4370(2) 0.0771(9) Uani 1 1 d . . . H5 H 0.4345 1.1737 0.4886 0.093 Uiso 1 1 calc R . . C6 C 0.5961(2) 1.1438(2) 0.43816(16) 0.0571(6) Uani 1 1 d . . . H6 H 0.6160 1.1130 0.4905 0.068 Uiso 1 1 calc R . . C7 C 0.89920(19) 1.17829(16) 0.41835(13) 0.0371(5) Uani 1 1 d . . . C8 C 0.9376(2) 1.28836(17) 0.42151(15) 0.0473(5) Uani 1 1 d . . . H8 H 0.8900 1.3231 0.3875 0.057 Uiso 1 1 calc R . . C9 C 1.0465(2) 1.3479(2) 0.47480(17) 0.0587(6) Uani 1 1 d . . . H9 H 1.0718 1.4232 0.4773 0.070 Uiso 1 1 calc R . . C10 C 1.1176(2) 1.2994(2) 0.52358(17) 0.0582(6) Uani 1 1 d . . . H10 H 1.1924 1.3409 0.5589 0.070 Uiso 1 1 calc R . . C11 C 1.0798(2) 1.1904(2) 0.52095(15) 0.0503(6) Uani 1 1 d . . . H11 H 1.1290 1.1564 0.5543 0.060 Uiso 1 1 calc R . . C12 C 0.9701(2) 1.12970(17) 0.46975(14) 0.0417(5) Uani 1 1 d . . . H12 H 0.9432 1.0544 0.4698 0.050 Uiso 1 1 calc R . . C13 C 0.78308(18) 1.02476(15) 0.31531(12) 0.0331(4) Uani 1 1 d . . . C14 C 0.89769(19) 1.00423(16) 0.28967(13) 0.0377(5) Uani 1 1 d . . . H14 H 0.9825 1.0529 0.3064 0.045 Uiso 1 1 calc R . . C15 C 0.88658(19) 0.91321(17) 0.24009(13) 0.0367(4) Uani 1 1 d . . . H15 H 0.9655 0.8994 0.2246 0.044 Uiso 1 1 calc R . . C16 C 0.76443(18) 0.83887(15) 0.21080(12) 0.0328(4) Uani 1 1 d . . . C17 C 0.64767(17) 0.85889(14) 0.23655(11) 0.0286(4) Uani 1 1 d . . . C18 C 0.66053(18) 0.95031(15) 0.28929(12) 0.0308(4) Uani 1 1 d . . . H18 H 0.5823 0.9628 0.3086 0.037 Uiso 1 1 calc R . . C19 C 0.50552(17) 0.77862(14) 0.21706(12) 0.0280(4) Uani 1 1 d . . . C20 C 0.47583(17) 0.73171(14) 0.11843(12) 0.0279(4) Uani 1 1 d . . . C21 C 0.55677(18) 0.68286(15) 0.07095(13) 0.0326(4) Uani 1 1 d . . . C22 C 0.68762(19) 0.68351(16) 0.09905(14) 0.0375(5) Uani 1 1 d . . . H22 H 0.7151 0.6288 0.0722 0.045 Uiso 1 1 calc R . . C23 C 0.77414(19) 0.74948(16) 0.15679(14) 0.0380(5) Uani 1 1 d . . . H23 H 0.8552 0.7358 0.1637 0.046 Uiso 1 1 calc R . . C24 C 0.5106(2) 0.62944(16) -0.01165(13) 0.0388(5) Uani 1 1 d . . . H24 H 0.5640 0.5955 -0.0427 0.047 Uiso 1 1 calc R . . C25 C 0.3911(2) 0.62403(16) -0.04980(13) 0.0391(5) Uani 1 1 d . . . H25 H 0.3623 0.5853 -0.1053 0.047 Uiso 1 1 calc R . . C26 C 0.31221(18) 0.67536(14) -0.00701(12) 0.0324(4) Uani 1 1 d . . . C27 C 0.35639(18) 0.72739(14) 0.07685(12) 0.0292(4) Uani 1 1 d . . . H27 H 0.3024 0.7615 0.1069 0.035 Uiso 1 1 calc R . . C28 C 0.18419(19) 0.66581(16) -0.04919(12) 0.0347(4) Uani 1 1 d . . . H28 H 0.1398 0.5987 -0.0783 0.042 Uiso 1 1 calc R . . C29 C 0.11947(18) 0.73607(15) -0.05346(12) 0.0318(4) Uani 1 1 d . . . C30 C 0.17258(18) 0.84931(15) -0.02025(12) 0.0315(4) Uani 1 1 d . . . C31 C 0.29916(19) 0.91490(16) -0.04216(13) 0.0382(5) Uani 1 1 d . . . H31 H 0.3555 0.8862 -0.0758 0.046 Uiso 1 1 calc R . . C32 C 0.3436(2) 1.02182(17) -0.01526(14) 0.0440(5) Uani 1 1 d . . . H32 H 0.4299 1.0655 -0.0309 0.053 Uiso 1 1 calc R . . C33 C 0.2637(2) 1.06510(17) 0.03386(14) 0.0431(5) Uani 1 1 d . . . H33 H 0.2943 1.1383 0.0519 0.052 Uiso 1 1 calc R . . C34 C 0.1386(2) 1.00076(17) 0.05652(14) 0.0420(5) Uani 1 1 d . . . H34 H 0.0835 1.0298 0.0911 0.050 Uiso 1 1 calc R . . C35 C 0.09299(19) 0.89429(16) 0.02926(13) 0.0370(4) Uani 1 1 d . . . H35 H 0.0062 0.8513 0.0446 0.044 Uiso 1 1 calc R . . C36 C -0.01192(19) 0.70216(15) -0.10120(12) 0.0340(4) Uani 1 1 d . . . C37 C -0.1053(2) 0.60203(16) -0.09110(14) 0.0395(5) Uani 1 1 d . . . H37 H -0.0888 0.5562 -0.0487 0.047 Uiso 1 1 calc R . . C38 C -0.2220(2) 0.56797(17) -0.14187(15) 0.0444(5) Uani 1 1 d . . . H38 H -0.2841 0.4990 -0.1348 0.053 Uiso 1 1 calc R . . C39 C -0.2475(2) 0.6348(2) -0.20284(16) 0.0523(6) Uani 1 1 d . . . H39 H -0.3269 0.6115 -0.2381 0.063 Uiso 1 1 calc R . . C40 C -0.1576(2) 0.7355(2) -0.21250(17) 0.0574(6) Uani 1 1 d . . . H40 H -0.1759 0.7816 -0.2537 0.069 Uiso 1 1 calc R . . C41 C -0.0406(2) 0.76904(18) -0.16199(14) 0.0457(5) Uani 1 1 d . . . H41 H 0.0207 0.8384 -0.1689 0.055 Uiso 1 1 calc R . . C42 C 0.47648(17) 0.68700(14) 0.28375(12) 0.0311(4) Uani 1 1 d . . . C43 C 0.5398(2) 0.61281(16) 0.29565(14) 0.0383(5) Uani 1 1 d . . . H43 H 0.6119 0.6120 0.2589 0.046 Uiso 1 1 calc R . . C44 C 0.4954(2) 0.53961(17) 0.36263(15) 0.0463(5) Uani 1 1 d . . . H44 H 0.5383 0.4887 0.3714 0.056 Uiso 1 1 calc R . . C45 C 0.3904(2) 0.53938(18) 0.41655(15) 0.0505(6) Uani 1 1 d . . . H45 H 0.3615 0.4882 0.4613 0.061 Uiso 1 1 calc R . . C46 C 0.3272(2) 0.61342(18) 0.40567(14) 0.0459(5) Uani 1 1 d . . . H46 H 0.2555 0.6138 0.4429 0.055 Uiso 1 1 calc R . . C47 C 0.37062(18) 0.68751(16) 0.33914(12) 0.0352(4) Uani 1 1 d . . . C48 C 0.32552(17) 0.77575(16) 0.31617(12) 0.0329(4) Uani 1 1 d . . . C49 C 0.22814(19) 0.81121(18) 0.35424(13) 0.0417(5) Uani 1 1 d . . . H49 H 0.1754 0.7741 0.4015 0.050 Uiso 1 1 calc R . . C50 C 0.2094(2) 0.90091(19) 0.32232(14) 0.0450(5) Uani 1 1 d . . . H50 H 0.1440 0.9261 0.3483 0.054 Uiso 1 1 calc R . . C51 C 0.2852(2) 0.95462(18) 0.25275(13) 0.0402(5) Uani 1 1 d . . . H51 H 0.2712 1.0164 0.2316 0.048 Uiso 1 1 calc R . . C52 C 0.38123(18) 0.91906(15) 0.21364(12) 0.0323(4) Uani 1 1 d . . . H52 H 0.4321 0.9554 0.1654 0.039 Uiso 1 1 calc R . . C53 C 0.40181(16) 0.82952(15) 0.24609(11) 0.0288(4) Uani 1 1 d . . . C54 C 0.9973(3) 0.5545(3) 0.2682(2) 0.0882(10) Uani 1 1 d . . . H54A H 1.0445 0.5020 0.2684 0.106 Uiso 1 1 calc R . . H54B H 1.0336 0.6066 0.3188 0.106 Uiso 1 1 calc R . . N1 N 0.78699(16) 1.11718(14) 0.36555(12) 0.0415(4) Uani 1 1 d . . . Cl1 Cl 1.02896(6) 0.62075(5) 0.16729(5) 0.0635(2) Uani 1 1 d . . . Cl2 Cl 0.82976(7) 0.48897(6) 0.28594(5) 0.0711(2) 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 0.0396(11) 0.0343(11) 0.0478(12) -0.0077(9) -0.0132(9) 0.0111(9) C2 0.0595(15) 0.0448(14) 0.0597(14) 0.0066(11) -0.0136(11) 0.0149(12) C3 0.0736(19) 0.0485(16) 0.102(2) 0.0090(15) -0.0339(17) 0.0254(14) C4 0.0601(17) 0.0646(19) 0.113(3) -0.0275(18) -0.0330(18) 0.0332(15) C5 0.0504(15) 0.102(2) 0.080(2) -0.0325(17) -0.0106(14) 0.0311(16) C6 0.0443(13) 0.0766(18) 0.0489(13) -0.0077(12) -0.0117(10) 0.0195(12) C7 0.0318(10) 0.0375(11) 0.0362(10) 0.0001(8) -0.0021(8) 0.0039(8) C8 0.0466(12) 0.0375(12) 0.0501(12) 0.0067(10) -0.0031(10) 0.0032(10) C9 0.0533(14) 0.0395(13) 0.0669(15) -0.0016(11) -0.0043(12) -0.0060(11) C10 0.0425(13) 0.0577(16) 0.0585(14) -0.0071(12) -0.0115(11) -0.0036(11) C11 0.0400(12) 0.0611(16) 0.0458(12) 0.0025(10) -0.0087(9) 0.0117(11) C12 0.0395(11) 0.0387(12) 0.0420(11) 0.0024(9) -0.0057(9) 0.0064(9) C13 0.0331(10) 0.0316(11) 0.0332(9) 0.0044(8) -0.0042(8) 0.0085(8) C14 0.0267(10) 0.0423(12) 0.0387(10) 0.0061(9) -0.0027(8) 0.0040(9) C15 0.0263(9) 0.0459(12) 0.0384(10) 0.0047(9) 0.0001(8) 0.0125(9) C16 0.0301(10) 0.0340(11) 0.0360(9) 0.0076(8) 0.0006(8) 0.0121(8) C17 0.0266(9) 0.0286(10) 0.0302(9) 0.0080(7) -0.0007(7) 0.0081(8) C18 0.0270(9) 0.0315(10) 0.0344(9) 0.0054(8) -0.0013(7) 0.0100(8) C19 0.0248(9) 0.0281(10) 0.0314(9) 0.0044(7) 0.0001(7) 0.0088(7) C20 0.0301(9) 0.0207(9) 0.0326(9) 0.0060(7) 0.0032(7) 0.0075(7) C21 0.0348(10) 0.0250(10) 0.0389(10) 0.0050(8) 0.0042(8) 0.0105(8) C22 0.0365(11) 0.0319(11) 0.0490(11) 0.0014(9) 0.0049(9) 0.0182(9) C23 0.0299(10) 0.0392(12) 0.0503(11) 0.0063(9) 0.0039(8) 0.0183(9) C24 0.0438(11) 0.0331(11) 0.0432(11) -0.0035(8) 0.0040(9) 0.0183(9) C25 0.0485(12) 0.0330(11) 0.0370(10) -0.0045(8) -0.0021(9) 0.0158(9) C26 0.0360(10) 0.0256(10) 0.0352(9) 0.0034(8) -0.0019(8) 0.0094(8) C27 0.0325(10) 0.0245(9) 0.0323(9) 0.0040(7) 0.0011(7) 0.0115(8) C28 0.0388(11) 0.0299(10) 0.0328(9) -0.0014(8) -0.0038(8) 0.0082(9) C29 0.0348(10) 0.0301(10) 0.0289(9) 0.0033(7) 0.0000(7) 0.0084(8) C30 0.0350(10) 0.0289(10) 0.0308(9) 0.0039(7) -0.0060(7) 0.0109(8) C31 0.0373(11) 0.0383(12) 0.0381(10) 0.0056(8) 0.0026(8) 0.0109(9) C32 0.0403(12) 0.0341(12) 0.0498(12) 0.0116(9) 0.0000(9) 0.0009(9) C33 0.0516(13) 0.0284(11) 0.0474(12) 0.0050(9) -0.0098(10) 0.0105(10) C34 0.0459(12) 0.0378(12) 0.0458(11) -0.0015(9) -0.0051(9) 0.0192(10) C35 0.0336(10) 0.0362(11) 0.0408(10) 0.0024(8) -0.0019(8) 0.0109(9) C36 0.0355(10) 0.0334(11) 0.0331(9) -0.0008(8) -0.0016(8) 0.0116(8) C37 0.0397(11) 0.0324(11) 0.0469(11) 0.0008(9) 0.0002(9) 0.0127(9) C38 0.0362(11) 0.0342(12) 0.0585(13) -0.0061(10) -0.0018(9) 0.0069(9) C39 0.0400(12) 0.0551(15) 0.0566(13) -0.0083(11) -0.0149(10) 0.0103(11) C40 0.0536(14) 0.0554(15) 0.0580(14) 0.0119(11) -0.0202(11) 0.0104(12) C41 0.0445(12) 0.0381(12) 0.0485(12) 0.0090(9) -0.0111(9) 0.0050(10) C42 0.0294(9) 0.0290(10) 0.0312(9) 0.0041(7) -0.0050(7) 0.0044(8) C43 0.0378(11) 0.0325(11) 0.0435(11) 0.0078(8) -0.0048(8) 0.0097(9) C44 0.0508(13) 0.0339(12) 0.0510(12) 0.0111(9) -0.0139(10) 0.0088(10) C45 0.0532(14) 0.0430(13) 0.0444(12) 0.0200(10) -0.0060(10) -0.0005(11) C46 0.0407(12) 0.0506(14) 0.0390(11) 0.0123(9) 0.0024(9) 0.0041(10) C47 0.0309(10) 0.0375(11) 0.0306(9) 0.0038(8) -0.0030(7) 0.0024(8) C48 0.0250(9) 0.0395(11) 0.0305(9) 0.0005(8) -0.0032(7) 0.0058(8) C49 0.0310(10) 0.0591(14) 0.0334(10) 0.0002(9) 0.0044(8) 0.0131(10) C50 0.0334(11) 0.0672(16) 0.0408(11) -0.0084(10) -0.0021(8) 0.0264(11) C51 0.0399(11) 0.0487(13) 0.0384(10) -0.0060(9) -0.0078(9) 0.0240(10) C52 0.0300(9) 0.0368(11) 0.0319(9) 0.0003(8) -0.0021(7) 0.0135(8) C53 0.0240(9) 0.0320(10) 0.0285(9) -0.0027(7) -0.0035(7) 0.0073(8) C54 0.0616(18) 0.124(3) 0.0691(19) 0.0066(18) -0.0050(14) 0.0171(18) N1 0.0357(9) 0.0373(10) 0.0501(10) -0.0063(8) -0.0130(7) 0.0113(8) Cl1 0.0596(4) 0.0545(4) 0.0817(4) 0.0060(3) 0.0121(3) 0.0256(3) Cl2 0.0620(4) 0.0648(4) 0.0788(5) 0.0071(3) 0.0006(3) 0.0102(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.382(3) . ? C1 C2 1.385(3) . ? C1 N1 1.437(3) . ? C2 C3 1.393(4) . ? C2 H2 0.9500 . ? C3 C4 1.367(5) . ? C3 H3 0.9500 . ? C4 C5 1.372(5) . ? C4 H4 0.9500 . ? C5 C6 1.392(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.388(3) . ? C7 C12 1.393(3) . ? C7 N1 1.421(2) . ? C8 C9 1.395(3) . ? C8 H8 0.9500 . ? C9 C10 1.372(4) . ? C9 H9 0.9500 . ? C10 C11 1.374(3) . ? C10 H10 0.9500 . ? C11 C12 1.389(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.395(3) . ? C13 C18 1.400(3) . ? C13 N1 1.407(3) . ? C14 C15 1.368(3) . ? C14 H14 0.9500 . ? C15 C16 1.409(3) . ? C15 H15 0.9500 . ? C16 C17 1.414(3) . ? C16 C23 1.446(3) . ? C17 C18 1.393(3) . ? C17 C19 1.562(2) . ? C18 H18 0.9500 . ? C19 C53 1.537(2) . ? C19 C42 1.556(2) . ? C19 C20 1.562(2) . ? C20 C27 1.401(3) . ? C20 C21 1.421(3) . ? C21 C24 1.399(3) . ? C21 C22 1.457(3) . ? C22 C23 1.329(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25 1.376(3) . ? C24 H24 0.9500 . ? C25 C26 1.394(3) . ? C25 H25 0.9500 . ? C26 C27 1.405(3) . ? C26 C28 1.469(3) . ? C27 H27 0.9500 . ? C28 C29 1.341(3) . ? C28 H28 0.9500 . ? C29 C30 1.491(3) . ? C29 C36 1.494(3) . ? C30 C35 1.393(3) . ? C30 C31 1.396(3) . ? C31 C32 1.389(3) . ? C31 H31 0.9500 . ? C32 C33 1.379(3) . ? C32 H32 0.9500 . ? C33 C34 1.381(3) . ? C33 H33 0.9500 . ? C34 C35 1.385(3) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 C37 1.393(3) . ? C36 C41 1.397(3) . ? C37 C38 1.388(3) . ? C37 H37 0.9500 . ? C38 C39 1.384(3) . ? C38 H38 0.9500 . ? C39 C40 1.383(3) . ? C39 H39 0.9500 . ? C40 C41 1.388(3) . ? C40 H40 0.9500 . ? C41 H41 0.9500 . ? C42 C43 1.389(3) . ? C42 C47 1.406(3) . ? C43 C44 1.395(3) . ? C43 H43 0.9500 . ? C44 C45 1.383(3) . ? C44 H44 0.9500 . ? C45 C46 1.384(3) . ? C45 H45 0.9500 . ? C46 C47 1.396(3) . ? C46 H46 0.9500 . ? C47 C48 1.464(3) . ? C48 C49 1.394(3) . ? C48 C53 1.395(3) . ? C49 C50 1.379(3) . ? C49 H49 0.9500 . ? C50 C51 1.386(3) . ? C50 H50 0.9500 . ? C51 C52 1.389(3) . ? C51 H51 0.9500 . ? C52 C53 1.389(3) . ? C52 H52 0.9500 . ? C54 Cl2 1.741(3) . ? C54 Cl1 1.750(3) . ? C54 H54A 0.9900 . ? C54 H54B 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 C6 C1 C2 119.7(2) . . ? C6 C1 N1 119.7(2) . . ? C2 C1 N1 120.6(2) . . ? C1 C2 C3 119.4(3) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 120.6(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 120.2(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 120.0(3) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C8 C7 C12 118.77(19) . . ? C8 C7 N1 120.04(18) . . ? C12 C7 N1 121.17(18) . . ? C7 C8 C9 119.7(2) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 121.1(2) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 119.4(2) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C10 C11 C12 120.3(2) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 120.6(2) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? C14 C13 C18 118.18(18) . . ? C14 C13 N1 122.32(17) . . ? C18 C13 N1 119.50(17) . . ? C15 C14 C13 119.22(18) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C16 123.54(18) . . ? C14 C15 H15 118.2 . . ? C16 C15 H15 118.2 . . ? C15 C16 C17 117.66(18) . . ? C15 C16 C23 115.00(17) . . ? C17 C16 C23 127.34(17) . . ? C18 C17 C16 118.10(16) . . ? C18 C17 C19 118.25(16) . . ? C16 C17 C19 123.36(16) . . ? C17 C18 C13 123.25(17) . . ? C17 C18 H18 118.4 . . ? C13 C18 H18 118.4 . . ? C53 C19 C42 100.56(14) . . ? C53 C19 C17 109.72(14) . . ? C42 C19 C17 109.27(14) . . ? C53 C19 C20 110.08(13) . . ? C42 C19 C20 109.95(14) . . ? C17 C19 C20 116.12(14) . . ? C27 C20 C21 117.24(16) . . ? C27 C20 C19 118.71(15) . . ? C21 C20 C19 123.73(15) . . ? C24 C21 C20 118.78(17) . . ? C24 C21 C22 114.91(17) . . ? C20 C21 C22 126.30(18) . . ? C23 C22 C21 129.46(19) . . ? C23 C22 H22 115.3 . . ? C21 C22 H22 115.3 . . ? C22 C23 C16 130.21(18) . . ? C22 C23 H23 114.9 . . ? C16 C23 H23 114.9 . . ? C25 C24 C21 122.67(18) . . ? C25 C24 H24 118.7 . . ? C21 C24 H24 118.7 . . ? C24 C25 C26 119.96(18) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C27 117.77(17) . . ? C25 C26 C28 118.16(17) . . ? C27 C26 C28 123.93(17) . . ? C20 C27 C26 123.47(17) . . ? C20 C27 H27 118.3 . . ? C26 C27 H27 118.3 . . ? C29 C28 C26 130.74(18) . . ? C29 C28 H28 114.6 . . ? C26 C28 H28 114.6 . . ? C28 C29 C30 125.16(17) . . ? C28 C29 C36 118.28(17) . . ? C30 C29 C36 116.39(16) . . ? C35 C30 C31 118.02(18) . . ? C35 C30 C29 120.31(17) . . ? C31 C30 C29 121.55(17) . . ? C32 C31 C30 120.63(19) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C33 C32 C31 120.64(19) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C34 C33 C32 119.2(2) . . ? C34 C33 H33 120.4 . . ? C32 C33 H33 120.4 . . ? C33 C34 C35 120.5(2) . . ? C33 C34 H34 119.7 . . ? C35 C34 H34 119.7 . . ? C34 C35 C30 120.93(19) . . ? C34 C35 H35 119.5 . . ? C30 C35 H35 119.5 . . ? C37 C36 C41 118.19(18) . . ? C37 C36 C29 121.74(17) . . ? C41 C36 C29 119.96(17) . . ? C38 C37 C36 121.14(19) . . ? C38 C37 H37 119.4 . . ? C36 C37 H37 119.4 . . ? C39 C38 C37 119.7(2) . . ? C39 C38 H38 120.1 . . ? C37 C38 H38 120.1 . . ? C38 C39 C40 120.1(2) . . ? C38 C39 H39 120.0 . . ? C40 C39 H39 120.0 . . ? C39 C40 C41 120.0(2) . . ? C39 C40 H40 120.0 . . ? C41 C40 H40 120.0 . . ? C40 C41 C36 120.8(2) . . ? C40 C41 H41 119.6 . . ? C36 C41 H41 119.6 . . ? C43 C42 C47 119.89(17) . . ? C43 C42 C19 130.12(17) . . ? C47 C42 C19 109.97(16) . . ? C42 C43 C44 118.6(2) . . ? C42 C43 H43 120.7 . . ? C44 C43 H43 120.7 . . ? C45 C44 C43 121.5(2) . . ? C45 C44 H44 119.2 . . ? C43 C44 H44 119.2 . . ? C44 C45 C46 120.32(19) . . ? C44 C45 H45 119.8 . . ? C46 C45 H45 119.8 . . ? C45 C46 C47 118.9(2) . . ? C45 C46 H46 120.5 . . ? C47 C46 H46 120.5 . . ? C46 C47 C42 120.70(19) . . ? C46 C47 C48 129.96(19) . . ? C42 C47 C48 109.30(16) . . ? C49 C48 C53 120.45(18) . . ? C49 C48 C47 130.68(18) . . ? C53 C48 C47 108.83(16) . . ? C50 C49 C48 119.04(19) . . ? C50 C49 H49 120.5 . . ? C48 C49 H49 120.5 . . ? C49 C50 C51 120.67(19) . . ? C49 C50 H50 119.7 . . ? C51 C50 H50 119.7 . . ? C50 C51 C52 120.7(2) . . ? C50 C51 H51 119.7 . . ? C52 C51 H51 119.7 . . ? C51 C52 C53 119.03(18) . . ? C51 C52 H52 120.5 . . ? C53 C52 H52 120.5 . . ? C52 C53 C48 120.13(17) . . ? C52 C53 C19 128.50(16) . . ? C48 C53 C19 111.34(16) . . ? Cl2 C54 Cl1 113.69(17) . . ? Cl2 C54 H54A 108.8 . . ? Cl1 C54 H54A 108.8 . . ? Cl2 C54 H54B 108.8 . . ? Cl1 C54 H54B 108.8 . . ? H54A C54 H54B 107.7 . . ? C13 N1 C7 122.63(16) . . ? C13 N1 C1 119.44(15) . . ? C7 N1 C1 117.92(16) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.338 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.072