# Electronic Supplementary Material (ESI) for Chemical Communications # 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_gusa9_2 #TrackingRef '18527_web_deposit_cif_file_0_TomoyaIshizuka_1363175702.singly-fused.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H34 N4 O Zn' _chemical_formula_weight 748.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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 10.995(3) _cell_length_b 13.281(4) _cell_length_c 13.404(4) _cell_angle_alpha 92.598(4) _cell_angle_beta 108.215(4) _cell_angle_gamma 99.610(4) _cell_volume 1823.3(9) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.718 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8938 _exptl_absorpt_correction_T_max 0.9788 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 9815 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 27.49 _reflns_number_total 7626 _reflns_number_gt 5430 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0750P)^2^+7.8885P] 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 7626 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1191 _refine_ls_R_factor_gt 0.0825 _refine_ls_wR_factor_ref 0.2244 _refine_ls_wR_factor_gt 0.2095 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.26310(6) 0.37088(5) 0.29521(5) 0.0325(2) Uani 1 1 d . . . O1 O 0.0524(4) 0.3520(3) 0.2721(4) 0.0464(11) Uani 1 1 d . . . N1 N 0.3098(5) 0.5308(4) 0.3402(4) 0.0369(11) Uani 1 1 d . . . N2 N 0.3192(5) 0.3443(4) 0.4473(4) 0.0388(11) Uani 1 1 d . . . N3 N 0.2556(4) 0.2153(4) 0.2615(3) 0.0326(10) Uani 1 1 d . . . N4 N 0.2471(4) 0.3967(3) 0.1468(3) 0.0324(10) Uani 1 1 d . . . C1 C 0.2963(6) 0.6035(4) 0.2720(5) 0.0364(13) Uani 1 1 d . . . C2 C 0.3156(7) 0.7037(5) 0.3282(5) 0.0457(15) Uani 1 1 d . . . H1 H 0.3094 0.7670 0.2985 0.055 Uiso 1 1 calc R . . C3 C 0.3442(6) 0.6888(5) 0.4311(5) 0.0442(15) Uani 1 1 d . . . H2 H 0.3629 0.7403 0.4882 0.053 Uiso 1 1 calc R . . C4 C 0.3413(6) 0.5827(5) 0.4389(4) 0.0389(13) Uani 1 1 d . . . C5 C 0.3591(5) 0.5278(4) 0.5284(4) 0.0370(13) Uani 1 1 d . . . C6 C 0.3451(6) 0.4217(4) 0.5251(4) 0.0363(12) Uani 1 1 d . . . C7 C 0.3583(6) 0.3837(5) 0.6250(5) 0.0391(13) Uani 1 1 d . . . C8 C 0.3374(6) 0.2791(5) 0.6088(4) 0.0409(14) Uani 1 1 d . . . C9 C 0.3147(6) 0.2554(5) 0.4949(4) 0.0357(12) Uani 1 1 d . . . C10 C 0.2917(5) 0.1595(4) 0.4394(4) 0.0335(12) Uani 1 1 d . . . C11 C 0.2710(5) 0.1419(4) 0.3293(4) 0.0329(12) Uani 1 1 d . . . C12 C 0.2681(5) 0.0457(4) 0.2742(4) 0.0351(12) Uani 1 1 d . . . H3 H 0.2762 -0.0175 0.3038 0.042 Uiso 1 1 calc R . . C13 C 0.2519(5) 0.0619(4) 0.1727(4) 0.0347(12) Uani 1 1 d . . . H4 H 0.2476 0.0126 0.1174 0.042 Uiso 1 1 calc R . . C14 C 0.2424(5) 0.1678(4) 0.1641(4) 0.0308(11) Uani 1 1 d . . . C15 C 0.2263(5) 0.2182(4) 0.0715(4) 0.0293(11) Uani 1 1 d . . . C16 C 0.2279(5) 0.3229(4) 0.0647(4) 0.0332(12) Uani 1 1 d . . . C17 C 0.2142(5) 0.3715(4) -0.0313(4) 0.0354(12) Uani 1 1 d . . . H5 H 0.2002 0.3383 -0.0993 0.042 Uiso 1 1 calc R . . C18 C 0.2248(6) 0.4725(4) -0.0064(4) 0.0370(13) Uani 1 1 d . . . H6 H 0.2191 0.5238 -0.0539 0.044 Uiso 1 1 calc R . . C19 C 0.2466(5) 0.4891(4) 0.1059(4) 0.0331(12) Uani 1 1 d . . . C20 C 0.2659(5) 0.5853(4) 0.1614(4) 0.0340(12) Uani 1 1 d . . . C21 C 0.3901(5) 0.5650(4) 0.6420(4) 0.0355(12) Uani 1 1 d . . . C22 C 0.3873(6) 0.4770(5) 0.6999(5) 0.0421(14) Uani 1 1 d . . . C23 C 0.4106(6) 0.4886(5) 0.8075(5) 0.0462(15) Uani 1 1 d . . . H7 H 0.4091 0.4302 0.8457 0.055 Uiso 1 1 calc R . . C24 C 0.4364(6) 0.5867(6) 0.8591(5) 0.0518(17) Uani 1 1 d . . . H8 H 0.4509 0.5953 0.9329 0.062 Uiso 1 1 calc R . . C25 C 0.4411(6) 0.6722(5) 0.8036(5) 0.0451(15) Uani 1 1 d . . . H9 H 0.4578 0.7389 0.8397 0.054 Uiso 1 1 calc R . . C26 C 0.4214(6) 0.6613(5) 0.6949(5) 0.0439(14) Uani 1 1 d . . . H10 H 0.4297 0.7203 0.6582 0.053 Uiso 1 1 calc R . . C27 C 0.2860(6) 0.0658(5) 0.4984(4) 0.0381(13) Uani 1 1 d . . . C28 C 0.1707(6) -0.0057(5) 0.4726(5) 0.0433(14) Uani 1 1 d . . . H11 H 0.0959 0.0056 0.4186 0.052 Uiso 1 1 calc R . . C29 C 0.1630(7) -0.0935(5) 0.5246(5) 0.0475(15) Uani 1 1 d . . . H12 H 0.0836 -0.1422 0.5056 0.057 Uiso 1 1 calc R . . C30 C 0.2710(7) -0.1099(5) 0.6040(5) 0.0472(15) Uani 1 1 d . . . H13 H 0.2660 -0.1698 0.6397 0.057 Uiso 1 1 calc R . . C31 C 0.3863(7) -0.0387(6) 0.6314(5) 0.0523(17) Uani 1 1 d . . . H14 H 0.4600 -0.0491 0.6872 0.063 Uiso 1 1 calc R . . C32 C 0.3946(6) 0.0475(5) 0.5777(5) 0.0451(15) Uani 1 1 d . . . H15 H 0.4751 0.0947 0.5952 0.054 Uiso 1 1 calc R . . C33 C 0.2062(5) 0.1532(4) -0.0292(4) 0.0307(11) Uani 1 1 d . . . C34 C 0.3036(6) 0.1582(5) -0.0729(4) 0.0379(13) Uani 1 1 d . . . H16 H 0.3852 0.2023 -0.0383 0.046 Uiso 1 1 calc R . . C35 C 0.2858(6) 0.1003(5) -0.1665(5) 0.0429(14) Uani 1 1 d . . . H17 H 0.3549 0.1047 -0.1954 0.051 Uiso 1 1 calc R . . C36 C 0.1688(6) 0.0369(5) -0.2174(5) 0.0436(14) Uani 1 1 d . . . H18 H 0.1555 -0.0012 -0.2829 0.052 Uiso 1 1 calc R . . C37 C 0.0711(6) 0.0285(5) -0.1740(5) 0.0490(16) Uani 1 1 d . . . H19 H -0.0094 -0.0173 -0.2078 0.059 Uiso 1 1 calc R . . C38 C 0.0899(6) 0.0871(5) -0.0799(5) 0.0456(15) Uani 1 1 d . . . H20 H 0.0215 0.0815 -0.0501 0.055 Uiso 1 1 calc R . . C39 C 0.2552(6) 0.6760(4) 0.0993(4) 0.0350(12) Uani 1 1 d . . . C40 C 0.3652(6) 0.7515(5) 0.1097(5) 0.0452(15) Uani 1 1 d . . . H21 H 0.4471 0.7463 0.1587 0.054 Uiso 1 1 calc R . . C41 C 0.3560(7) 0.8331(5) 0.0498(6) 0.0500(16) Uani 1 1 d . . . H22 H 0.4312 0.8840 0.0581 0.060 Uiso 1 1 calc R . . C42 C 0.2383(7) 0.8410(5) -0.0219(5) 0.0468(15) Uani 1 1 d . . . H23 H 0.2326 0.8967 -0.0642 0.056 Uiso 1 1 calc R . . C43 C 0.1286(7) 0.7683(5) -0.0326(5) 0.0476(15) Uani 1 1 d . . . H24 H 0.0469 0.7750 -0.0809 0.057 Uiso 1 1 calc R . . C44 C 0.1367(6) 0.6856(5) 0.0268(5) 0.0433(14) Uani 1 1 d . . . H25 H 0.0609 0.6352 0.0179 0.052 Uiso 1 1 calc R . . C45 C -0.0088(7) 0.2864(6) 0.3309(6) 0.0556(18) Uani 1 1 d . . . H26 H 0.0475 0.2385 0.3651 0.067 Uiso 1 1 calc R . . H27 H -0.0935 0.2461 0.2846 0.067 Uiso 1 1 calc R . . C46 C -0.0283(8) 0.3578(7) 0.4118(7) 0.068(2) Uani 1 1 d . . . H28 H 0.0434 0.3646 0.4798 0.082 Uiso 1 1 calc R . . H29 H -0.1124 0.3336 0.4237 0.082 Uiso 1 1 calc R . . C47 C -0.0278(9) 0.4618(7) 0.3618(8) 0.082(3) Uani 1 1 d . . . H30 H -0.1102 0.4864 0.3539 0.098 Uiso 1 1 calc R . . H31 H 0.0462 0.5151 0.4057 0.098 Uiso 1 1 calc R . . C48 C -0.0140(8) 0.4370(6) 0.2562(6) 0.065(2) Uani 1 1 d . . . H32 H -0.1004 0.4176 0.2008 0.078 Uiso 1 1 calc R . . H33 H 0.0381 0.4960 0.2362 0.078 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 Zn1 0.0380(4) 0.0339(4) 0.0267(3) -0.0005(2) 0.0144(3) 0.0031(3) O1 0.046(2) 0.048(3) 0.057(3) 0.019(2) 0.030(2) 0.014(2) N1 0.037(3) 0.040(3) 0.033(2) -0.006(2) 0.014(2) 0.005(2) N2 0.040(3) 0.040(3) 0.032(2) -0.005(2) 0.011(2) 0.002(2) N3 0.034(2) 0.038(3) 0.026(2) -0.0007(19) 0.0143(19) -0.0013(19) N4 0.039(3) 0.031(2) 0.030(2) 0.0012(19) 0.016(2) 0.0050(19) C1 0.039(3) 0.033(3) 0.041(3) 0.001(2) 0.022(3) 0.001(2) C2 0.066(4) 0.030(3) 0.046(3) 0.001(3) 0.028(3) 0.003(3) C3 0.062(4) 0.030(3) 0.043(3) -0.002(3) 0.024(3) 0.003(3) C4 0.039(3) 0.047(4) 0.033(3) 0.000(3) 0.016(2) 0.006(3) C5 0.035(3) 0.039(3) 0.037(3) -0.001(2) 0.014(2) 0.002(2) C6 0.040(3) 0.035(3) 0.033(3) -0.001(2) 0.014(2) 0.003(2) C7 0.039(3) 0.046(4) 0.036(3) 0.004(3) 0.019(3) 0.009(3) C8 0.050(4) 0.046(4) 0.029(3) 0.000(2) 0.015(3) 0.010(3) C9 0.040(3) 0.041(3) 0.027(3) 0.001(2) 0.014(2) 0.006(2) C10 0.035(3) 0.038(3) 0.029(3) 0.007(2) 0.013(2) 0.006(2) C11 0.031(3) 0.036(3) 0.033(3) -0.002(2) 0.013(2) 0.003(2) C12 0.039(3) 0.033(3) 0.032(3) 0.005(2) 0.013(2) 0.004(2) C13 0.037(3) 0.034(3) 0.033(3) -0.001(2) 0.013(2) 0.005(2) C14 0.038(3) 0.027(3) 0.028(3) -0.001(2) 0.015(2) 0.002(2) C15 0.031(3) 0.033(3) 0.025(2) -0.001(2) 0.013(2) 0.002(2) C16 0.033(3) 0.038(3) 0.028(3) -0.001(2) 0.013(2) 0.000(2) C17 0.039(3) 0.038(3) 0.029(3) -0.001(2) 0.014(2) 0.002(2) C18 0.044(3) 0.036(3) 0.034(3) 0.005(2) 0.016(3) 0.008(2) C19 0.032(3) 0.034(3) 0.036(3) 0.001(2) 0.017(2) 0.003(2) C20 0.032(3) 0.037(3) 0.034(3) -0.001(2) 0.014(2) 0.003(2) C21 0.034(3) 0.037(3) 0.034(3) -0.007(2) 0.014(2) 0.002(2) C22 0.042(3) 0.046(4) 0.039(3) 0.001(3) 0.018(3) 0.004(3) C23 0.052(4) 0.052(4) 0.037(3) 0.000(3) 0.019(3) 0.007(3) C24 0.050(4) 0.069(5) 0.031(3) -0.014(3) 0.013(3) 0.003(3) C25 0.044(3) 0.049(4) 0.038(3) -0.008(3) 0.010(3) 0.006(3) C26 0.047(4) 0.042(4) 0.046(3) 0.000(3) 0.018(3) 0.011(3) C27 0.051(4) 0.041(3) 0.029(3) 0.005(2) 0.020(3) 0.011(3) C28 0.052(4) 0.044(4) 0.035(3) 0.006(3) 0.016(3) 0.008(3) C29 0.051(4) 0.048(4) 0.046(4) 0.009(3) 0.022(3) 0.004(3) C30 0.067(4) 0.041(4) 0.047(4) 0.011(3) 0.032(3) 0.017(3) C31 0.055(4) 0.065(5) 0.046(4) 0.017(3) 0.022(3) 0.024(3) C32 0.044(3) 0.057(4) 0.037(3) 0.011(3) 0.016(3) 0.007(3) C33 0.035(3) 0.032(3) 0.024(2) 0.000(2) 0.011(2) 0.003(2) C34 0.037(3) 0.041(3) 0.032(3) -0.002(2) 0.011(2) 0.000(2) C35 0.046(3) 0.053(4) 0.034(3) 0.003(3) 0.018(3) 0.010(3) C36 0.045(3) 0.052(4) 0.032(3) -0.006(3) 0.013(3) 0.008(3) C37 0.045(4) 0.053(4) 0.042(3) -0.014(3) 0.008(3) 0.009(3) C38 0.044(3) 0.051(4) 0.042(3) -0.005(3) 0.018(3) 0.004(3) C39 0.043(3) 0.029(3) 0.035(3) 0.000(2) 0.017(2) 0.006(2) C40 0.037(3) 0.046(4) 0.050(4) 0.003(3) 0.012(3) 0.006(3) C41 0.052(4) 0.035(3) 0.063(4) 0.008(3) 0.021(3) 0.004(3) C42 0.063(4) 0.037(3) 0.045(3) 0.008(3) 0.019(3) 0.019(3) C43 0.051(4) 0.044(4) 0.050(4) 0.002(3) 0.012(3) 0.024(3) C44 0.040(3) 0.039(3) 0.050(4) -0.006(3) 0.015(3) 0.007(3) C45 0.063(4) 0.053(4) 0.060(4) 0.015(3) 0.032(4) 0.011(3) C46 0.067(5) 0.072(5) 0.069(5) 0.005(4) 0.032(4) 0.004(4) C47 0.074(6) 0.068(6) 0.116(8) -0.001(5) 0.049(6) 0.017(4) C48 0.060(5) 0.069(5) 0.066(5) 0.013(4) 0.021(4) 0.015(4) _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 Zn1 N4 1.993(4) . ? Zn1 N2 2.003(5) . ? Zn1 N3 2.078(5) . ? Zn1 N1 2.113(5) . ? Zn1 O1 2.208(4) . ? O1 C45 1.425(7) . ? O1 C48 1.433(9) . ? N1 C1 1.354(7) . ? N1 C4 1.376(7) . ? N2 C6 1.358(7) . ? N2 C9 1.368(8) . ? N3 C11 1.358(7) . ? N3 C14 1.379(6) . ? N4 C19 1.367(7) . ? N4 C16 1.379(7) . ? C1 C20 1.415(8) . ? C1 C2 1.448(8) . ? C2 C3 1.347(9) . ? C3 C4 1.414(9) . ? C4 C5 1.410(8) . ? C5 C6 1.390(8) . ? C5 C21 1.494(8) . ? C6 C7 1.425(8) . ? C7 C8 1.365(9) . ? C7 C22 1.483(8) . ? C8 C9 1.478(7) . ? C9 C10 1.390(8) . ? C10 C11 1.422(7) . ? C10 C27 1.507(8) . ? C11 C12 1.438(8) . ? C12 C13 1.349(7) . ? C13 C14 1.435(8) . ? C14 C15 1.413(7) . ? C15 C16 1.395(8) . ? C15 C33 1.504(7) . ? C16 C17 1.443(7) . ? C17 C18 1.345(8) . ? C18 C19 1.448(8) . ? C19 C20 1.398(8) . ? C20 C39 1.495(8) . ? C21 C26 1.371(8) . ? C21 C22 1.433(9) . ? C22 C23 1.380(8) . ? C23 C24 1.389(9) . ? C24 C25 1.389(10) . ? C25 C26 1.401(8) . ? C27 C28 1.386(8) . ? C27 C32 1.394(9) . ? C28 C29 1.390(9) . ? C29 C30 1.381(9) . ? C30 C31 1.383(10) . ? C31 C32 1.385(9) . ? C33 C34 1.366(8) . ? C33 C38 1.376(8) . ? C34 C35 1.383(8) . ? C35 C36 1.366(8) . ? C36 C37 1.365(9) . ? C37 C38 1.391(8) . ? C39 C44 1.390(8) . ? C39 C40 1.402(8) . ? C40 C41 1.376(9) . ? C41 C42 1.374(9) . ? C42 C43 1.378(9) . ? C43 C44 1.384(9) . ? C45 C46 1.497(11) . ? C46 C47 1.562(12) . ? C47 C48 1.497(12) . ? 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 N4 Zn1 N2 167.65(19) . . ? N4 Zn1 N3 91.45(18) . . ? N2 Zn1 N3 86.04(19) . . ? N4 Zn1 N1 89.95(18) . . ? N2 Zn1 N1 90.28(19) . . ? N3 Zn1 N1 169.01(18) . . ? N4 Zn1 O1 95.38(17) . . ? N2 Zn1 O1 96.85(18) . . ? N3 Zn1 O1 94.02(17) . . ? N1 Zn1 O1 96.69(17) . . ? C45 O1 C48 105.7(5) . . ? C45 O1 Zn1 122.1(4) . . ? C48 O1 Zn1 121.8(4) . . ? C1 N1 C4 105.6(5) . . ? C1 N1 Zn1 124.7(4) . . ? C4 N1 Zn1 129.1(4) . . ? C6 N2 C9 106.0(5) . . ? C6 N2 Zn1 120.7(4) . . ? C9 N2 Zn1 132.0(4) . . ? C11 N3 C14 106.3(4) . . ? C11 N3 Zn1 128.2(3) . . ? C14 N3 Zn1 125.4(4) . . ? C19 N4 C16 107.2(4) . . ? C19 N4 Zn1 126.8(4) . . ? C16 N4 Zn1 125.9(4) . . ? N1 C1 C20 125.5(5) . . ? N1 C1 C2 110.4(5) . . ? C20 C1 C2 124.2(5) . . ? C3 C2 C1 106.0(5) . . ? C2 C3 C4 107.7(5) . . ? N1 C4 C5 119.8(6) . . ? N1 C4 C3 110.4(5) . . ? C5 C4 C3 129.7(5) . . ? C6 C5 C4 124.4(5) . . ? C6 C5 C21 105.2(5) . . ? C4 C5 C21 130.3(5) . . ? N2 C6 C5 134.5(5) . . ? N2 C6 C7 111.6(5) . . ? C5 C6 C7 113.9(5) . . ? C8 C7 C6 107.3(5) . . ? C8 C7 C22 148.2(6) . . ? C6 C7 C22 104.6(5) . . ? C7 C8 C9 105.2(5) . . ? N2 C9 C10 122.3(5) . . ? N2 C9 C8 109.9(5) . . ? C10 C9 C8 127.7(5) . . ? C9 C10 C11 124.9(5) . . ? C9 C10 C27 118.5(5) . . ? C11 C10 C27 116.6(5) . . ? N3 C11 C10 124.6(5) . . ? N3 C11 C12 110.0(5) . . ? C10 C11 C12 125.4(5) . . ? C13 C12 C11 107.2(5) . . ? C12 C13 C14 106.8(5) . . ? N3 C14 C15 124.2(5) . . ? N3 C14 C13 109.7(5) . . ? C15 C14 C13 126.0(5) . . ? C16 C15 C14 126.2(5) . . ? C16 C15 C33 116.8(5) . . ? C14 C15 C33 117.1(5) . . ? N4 C16 C15 126.7(5) . . ? N4 C16 C17 109.1(5) . . ? C15 C16 C17 124.2(5) . . ? C18 C17 C16 107.1(5) . . ? C17 C18 C19 107.8(5) . . ? N4 C19 C20 126.9(5) . . ? N4 C19 C18 108.8(5) . . ? C20 C19 C18 124.3(5) . . ? C19 C20 C1 124.9(5) . . ? C19 C20 C39 117.6(5) . . ? C1 C20 C39 117.5(5) . . ? C26 C21 C22 119.5(5) . . ? C26 C21 C5 132.5(6) . . ? C22 C21 C5 107.9(5) . . ? C23 C22 C21 120.5(6) . . ? C23 C22 C7 131.2(6) . . ? C21 C22 C7 108.3(5) . . ? C22 C23 C24 119.2(6) . . ? C25 C24 C23 120.4(6) . . ? C24 C25 C26 120.7(6) . . ? C21 C26 C25 119.5(6) . . ? C28 C27 C32 118.5(6) . . ? C28 C27 C10 119.7(5) . . ? C32 C27 C10 121.8(5) . . ? C27 C28 C29 121.0(6) . . ? C30 C29 C28 119.8(6) . . ? C29 C30 C31 119.8(6) . . ? C30 C31 C32 120.2(6) . . ? C31 C32 C27 120.6(6) . . ? C34 C33 C38 118.2(5) . . ? C34 C33 C15 120.6(5) . . ? C38 C33 C15 121.3(5) . . ? C33 C34 C35 121.3(5) . . ? C36 C35 C34 120.0(6) . . ? C37 C36 C35 119.8(6) . . ? C36 C37 C38 119.7(6) . . ? C33 C38 C37 121.0(6) . . ? C44 C39 C40 118.3(6) . . ? C44 C39 C20 120.8(5) . . ? C40 C39 C20 120.9(5) . . ? C41 C40 C39 120.8(6) . . ? C40 C41 C42 120.1(6) . . ? C41 C42 C43 120.0(6) . . ? C42 C43 C44 120.4(6) . . ? C43 C44 C39 120.3(6) . . ? O1 C45 C46 104.6(6) . . ? C45 C46 C47 103.5(6) . . ? C48 C47 C46 104.2(7) . . ? O1 C48 C47 103.3(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Zn1 O1 C45 149.3(5) . . . . ? N2 Zn1 O1 C45 -29.0(5) . . . . ? N3 Zn1 O1 C45 57.5(5) . . . . ? N1 Zn1 O1 C45 -120.1(5) . . . . ? N4 Zn1 O1 C48 -70.8(5) . . . . ? N2 Zn1 O1 C48 110.8(5) . . . . ? N3 Zn1 O1 C48 -162.7(5) . . . . ? N1 Zn1 O1 C48 19.7(5) . . . . ? N4 Zn1 N1 C1 11.9(4) . . . . ? N2 Zn1 N1 C1 179.6(5) . . . . ? N3 Zn1 N1 C1 109.3(9) . . . . ? O1 Zn1 N1 C1 -83.5(4) . . . . ? N4 Zn1 N1 C4 -177.9(5) . . . . ? N2 Zn1 N1 C4 -10.2(5) . . . . ? N3 Zn1 N1 C4 -80.5(10) . . . . ? O1 Zn1 N1 C4 86.7(5) . . . . ? N4 Zn1 N2 C6 101.4(10) . . . . ? N3 Zn1 N2 C6 180.0(4) . . . . ? N1 Zn1 N2 C6 10.3(4) . . . . ? O1 Zn1 N2 C6 -86.4(4) . . . . ? N4 Zn1 N2 C9 -93.6(10) . . . . ? N3 Zn1 N2 C9 -15.0(5) . . . . ? N1 Zn1 N2 C9 175.3(5) . . . . ? O1 Zn1 N2 C9 78.6(5) . . . . ? N4 Zn1 N3 C11 174.5(5) . . . . ? N2 Zn1 N3 C11 6.6(4) . . . . ? N1 Zn1 N3 C11 77.3(10) . . . . ? O1 Zn1 N3 C11 -90.0(4) . . . . ? N4 Zn1 N3 C14 -0.6(4) . . . . ? N2 Zn1 N3 C14 -168.5(4) . . . . ? N1 Zn1 N3 C14 -97.9(10) . . . . ? O1 Zn1 N3 C14 94.9(4) . . . . ? N2 Zn1 N4 C19 -101.0(10) . . . . ? N3 Zn1 N4 C19 -179.0(4) . . . . ? N1 Zn1 N4 C19 -9.9(4) . . . . ? O1 Zn1 N4 C19 86.8(4) . . . . ? N2 Zn1 N4 C16 82.5(10) . . . . ? N3 Zn1 N4 C16 4.5(4) . . . . ? N1 Zn1 N4 C16 173.6(4) . . . . ? O1 Zn1 N4 C16 -89.7(4) . . . . ? C4 N1 C1 C20 179.0(5) . . . . ? Zn1 N1 C1 C20 -8.9(8) . . . . ? C4 N1 C1 C2 -1.8(6) . . . . ? Zn1 N1 C1 C2 170.3(4) . . . . ? N1 C1 C2 C3 1.6(7) . . . . ? C20 C1 C2 C3 -179.2(6) . . . . ? C1 C2 C3 C4 -0.6(7) . . . . ? C1 N1 C4 C5 178.4(5) . . . . ? Zn1 N1 C4 C5 6.8(8) . . . . ? C1 N1 C4 C3 1.4(6) . . . . ? Zn1 N1 C4 C3 -170.2(4) . . . . ? C2 C3 C4 N1 -0.5(7) . . . . ? C2 C3 C4 C5 -177.1(6) . . . . ? N1 C4 C5 C6 -1.0(9) . . . . ? C3 C4 C5 C6 175.4(6) . . . . ? N1 C4 C5 C21 -178.4(5) . . . . ? C3 C4 C5 C21 -2.1(11) . . . . ? C9 N2 C6 C5 -178.4(6) . . . . ? Zn1 N2 C6 C5 -10.0(9) . . . . ? C9 N2 C6 C7 0.2(6) . . . . ? Zn1 N2 C6 C7 168.6(4) . . . . ? C4 C5 C6 N2 3.1(11) . . . . ? C21 C5 C6 N2 -178.9(6) . . . . ? C4 C5 C6 C7 -175.5(5) . . . . ? C21 C5 C6 C7 2.5(7) . . . . ? N2 C6 C7 C8 -1.2(7) . . . . ? C5 C6 C7 C8 177.7(5) . . . . ? N2 C6 C7 C22 179.5(5) . . . . ? C5 C6 C7 C22 -1.6(7) . . . . ? C6 C7 C8 C9 1.6(6) . . . . ? C22 C7 C8 C9 -179.6(9) . . . . ? C6 N2 C9 C10 -179.2(5) . . . . ? Zn1 N2 C9 C10 14.2(9) . . . . ? C6 N2 C9 C8 0.9(6) . . . . ? Zn1 N2 C9 C8 -165.8(4) . . . . ? C7 C8 C9 N2 -1.6(7) . . . . ? C7 C8 C9 C10 178.5(6) . . . . ? N2 C9 C10 C11 0.3(9) . . . . ? C8 C9 C10 C11 -179.7(6) . . . . ? N2 C9 C10 C27 -178.8(5) . . . . ? C8 C9 C10 C27 1.1(9) . . . . ? C14 N3 C11 C10 178.1(5) . . . . ? Zn1 N3 C11 C10 2.2(8) . . . . ? C14 N3 C11 C12 0.2(6) . . . . ? Zn1 N3 C11 C12 -175.7(4) . . . . ? C9 C10 C11 N3 -8.3(9) . . . . ? C27 C10 C11 N3 170.9(5) . . . . ? C9 C10 C11 C12 169.3(6) . . . . ? C27 C10 C11 C12 -11.5(8) . . . . ? N3 C11 C12 C13 0.5(6) . . . . ? C10 C11 C12 C13 -177.4(5) . . . . ? C11 C12 C13 C14 -1.0(6) . . . . ? C11 N3 C14 C15 -178.9(5) . . . . ? Zn1 N3 C14 C15 -2.9(7) . . . . ? C11 N3 C14 C13 -0.8(6) . . . . ? Zn1 N3 C14 C13 175.2(4) . . . . ? C12 C13 C14 N3 1.2(6) . . . . ? C12 C13 C14 C15 179.2(5) . . . . ? N3 C14 C15 C16 3.5(9) . . . . ? C13 C14 C15 C16 -174.3(5) . . . . ? N3 C14 C15 C33 -176.8(5) . . . . ? C13 C14 C15 C33 5.4(8) . . . . ? C19 N4 C16 C15 177.5(5) . . . . ? Zn1 N4 C16 C15 -5.4(8) . . . . ? C19 N4 C16 C17 -0.3(6) . . . . ? Zn1 N4 C16 C17 176.8(4) . . . . ? C14 C15 C16 N4 0.9(9) . . . . ? C33 C15 C16 N4 -178.8(5) . . . . ? C14 C15 C16 C17 178.5(5) . . . . ? C33 C15 C16 C17 -1.2(8) . . . . ? N4 C16 C17 C18 -0.1(6) . . . . ? C15 C16 C17 C18 -178.0(5) . . . . ? C16 C17 C18 C19 0.5(6) . . . . ? C16 N4 C19 C20 -178.3(5) . . . . ? Zn1 N4 C19 C20 4.7(8) . . . . ? C16 N4 C19 C18 0.6(6) . . . . ? Zn1 N4 C19 C18 -176.4(4) . . . . ? C17 C18 C19 N4 -0.7(6) . . . . ? C17 C18 C19 C20 178.2(5) . . . . ? N4 C19 C20 C1 3.4(9) . . . . ? C18 C19 C20 C1 -175.3(5) . . . . ? N4 C19 C20 C39 -177.4(5) . . . . ? C18 C19 C20 C39 3.9(8) . . . . ? N1 C1 C20 C19 -0.7(9) . . . . ? C2 C1 C20 C19 -179.8(6) . . . . ? N1 C1 C20 C39 -180.0(5) . . . . ? C2 C1 C20 C39 0.9(8) . . . . ? C6 C5 C21 C26 175.6(6) . . . . ? C4 C5 C21 C26 -6.6(11) . . . . ? C6 C5 C21 C22 -2.4(6) . . . . ? C4 C5 C21 C22 175.4(6) . . . . ? C26 C21 C22 C23 2.6(9) . . . . ? C5 C21 C22 C23 -179.0(5) . . . . ? C26 C21 C22 C7 -176.8(5) . . . . ? C5 C21 C22 C7 1.5(6) . . . . ? C8 C7 C22 C23 1.8(15) . . . . ? C6 C7 C22 C23 -179.5(6) . . . . ? C8 C7 C22 C21 -178.8(9) . . . . ? C6 C7 C22 C21 -0.1(6) . . . . ? C21 C22 C23 C24 0.3(9) . . . . ? C7 C22 C23 C24 179.6(6) . . . . ? C22 C23 C24 C25 -1.2(10) . . . . ? C23 C24 C25 C26 -0.7(10) . . . . ? C22 C21 C26 C25 -4.5(9) . . . . ? C5 C21 C26 C25 177.6(6) . . . . ? C24 C25 C26 C21 3.6(9) . . . . ? C9 C10 C27 C28 116.2(6) . . . . ? C11 C10 C27 C28 -63.1(7) . . . . ? C9 C10 C27 C32 -64.9(8) . . . . ? C11 C10 C27 C32 115.9(6) . . . . ? C32 C27 C28 C29 0.1(9) . . . . ? C10 C27 C28 C29 179.1(5) . . . . ? C27 C28 C29 C30 0.7(10) . . . . ? C28 C29 C30 C31 0.0(10) . . . . ? C29 C30 C31 C32 -1.6(10) . . . . ? C30 C31 C32 C27 2.4(10) . . . . ? C28 C27 C32 C31 -1.7(9) . . . . ? C10 C27 C32 C31 179.3(6) . . . . ? C16 C15 C33 C34 73.2(7) . . . . ? C14 C15 C33 C34 -106.6(6) . . . . ? C16 C15 C33 C38 -106.9(6) . . . . ? C14 C15 C33 C38 73.4(7) . . . . ? C38 C33 C34 C35 1.3(9) . . . . ? C15 C33 C34 C35 -178.8(6) . . . . ? C33 C34 C35 C36 0.3(10) . . . . ? C34 C35 C36 C37 -2.1(10) . . . . ? C35 C36 C37 C38 2.2(11) . . . . ? C34 C33 C38 C37 -1.2(10) . . . . ? C15 C33 C38 C37 178.9(6) . . . . ? C36 C37 C38 C33 -0.6(11) . . . . ? C19 C20 C39 C44 65.9(7) . . . . ? C1 C20 C39 C44 -114.8(6) . . . . ? C19 C20 C39 C40 -111.7(6) . . . . ? C1 C20 C39 C40 67.6(7) . . . . ? C44 C39 C40 C41 0.1(9) . . . . ? C20 C39 C40 C41 177.8(6) . . . . ? C39 C40 C41 C42 -0.5(10) . . . . ? C40 C41 C42 C43 1.3(10) . . . . ? C41 C42 C43 C44 -1.7(10) . . . . ? C42 C43 C44 C39 1.2(9) . . . . ? C40 C39 C44 C43 -0.4(9) . . . . ? C20 C39 C44 C43 -178.1(5) . . . . ? C48 O1 C45 C46 -41.9(8) . . . . ? Zn1 O1 C45 C46 103.4(6) . . . . ? O1 C45 C46 C47 23.1(8) . . . . ? C45 C46 C47 C48 2.4(9) . . . . ? C45 O1 C48 C47 43.2(8) . . . . ? Zn1 O1 C48 C47 -102.3(6) . . . . ? C46 C47 C48 O1 -26.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.911 _refine_diff_density_max 1.158 _refine_diff_density_min -0.879 _refine_diff_density_rms 0.097 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 0.013 0.264 0.712 66 9 ' ' 2 -0.014 0.736 0.287 66 9 ' ' 3 0.468 0.926 0.878 20 1 ' ' 4 0.532 0.074 0.123 20 1 ' ' _database_code_depnum_ccdc_archive 'CCDC 929175' ####################################################################### # # 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_gusa10_2 #TrackingRef 'web_deposit_cif_file_1_TomoyaIshizuka_1363175702.cis-doubly-fused.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H24 N4 Zn' _chemical_formula_weight 674.04 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' Zn Zn 0.2839 1.4301 '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 1 21/n 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.9576(14) _cell_length_b 8.0178(8) _cell_length_c 25.842(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.1530(10) _cell_angle_gamma 90.00 _cell_volume 2862.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 116(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.903 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8994 _exptl_absorpt_correction_T_max 0.9563 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 116(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 15619 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.58 _reflns_number_total 6456 _reflns_number_gt 5559 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0530P)^2^+1.5946P] 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 6456 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 Zn1 Zn 0.510134(15) 0.30110(3) 0.970380(8) 0.02059(8) Uani 1 1 d . . . N1 N 0.50986(12) 0.1934(2) 1.04600(6) 0.0203(3) Uani 1 1 d . . . N2 N 0.37900(12) 0.3899(2) 0.96984(6) 0.0223(3) Uani 1 1 d . . . N3 N 0.50453(11) 0.3809(2) 0.89355(6) 0.0205(3) Uani 1 1 d . . . N4 N 0.64164(11) 0.2229(2) 0.96764(6) 0.0199(3) Uani 1 1 d . . . C1 C 0.58201(13) 0.0983(2) 1.07296(7) 0.0202(4) Uani 1 1 d . . . C2 C 0.54926(14) 0.0302(3) 1.11931(7) 0.0239(4) Uani 1 1 d . . . H1 H 0.5850 -0.0411 1.1443 0.029 Uiso 1 1 calc R . . C3 C 0.45874(14) 0.0867(3) 1.12039(7) 0.0235(4) Uani 1 1 d . . . H2 H 0.4189 0.0634 1.1464 0.028 Uiso 1 1 calc R . . C4 C 0.43342(14) 0.1899(2) 1.07437(7) 0.0203(4) Uani 1 1 d . . . C5 C 0.34619(14) 0.2698(2) 1.05679(7) 0.0209(4) Uani 1 1 d . . . C6 C 0.32686(14) 0.3541(3) 1.00861(7) 0.0212(4) Uani 1 1 d . . . C7 C 0.22712(14) 0.3954(3) 0.99540(7) 0.0229(4) Uani 1 1 d . . . C8 C 0.21603(14) 0.4548(3) 0.94548(7) 0.0229(4) Uani 1 1 d . . . H3 H 0.1577 0.4921 0.9254 0.028 Uiso 1 1 calc R . . C9 C 0.31232(13) 0.4497(3) 0.92903(7) 0.0215(4) Uani 1 1 d . . . C10 C 0.33498(14) 0.4817(2) 0.87874(7) 0.0211(4) Uani 1 1 d . . . C11 C 0.42837(13) 0.4567(2) 0.86358(7) 0.0206(4) Uani 1 1 d . . . C12 C 0.45579(14) 0.5018(3) 0.81381(7) 0.0237(4) Uani 1 1 d . . . H4 H 0.4164 0.5572 0.7860 0.028 Uiso 1 1 calc R . . C13 C 0.54842(13) 0.4503(3) 0.81394(7) 0.0218(4) Uani 1 1 d . . . H5 H 0.5860 0.4631 0.7863 0.026 Uiso 1 1 calc R . . C14 C 0.57904(13) 0.3730(2) 0.86369(7) 0.0199(4) Uani 1 1 d . . . C15 C 0.67089(14) 0.3003(2) 0.87960(7) 0.0192(4) Uani 1 1 d . . . C16 C 0.70128(13) 0.2311(2) 0.92904(7) 0.0199(4) Uani 1 1 d . . . C17 C 0.79330(13) 0.1494(3) 0.94768(7) 0.0210(4) Uani 1 1 d . . . H6 H 0.8473 0.1383 0.9293 0.025 Uiso 1 1 calc R . . C18 C 0.78618(13) 0.0922(2) 0.99681(7) 0.0207(4) Uani 1 1 d . . . C19 C 0.69171(13) 0.1381(2) 1.00717(7) 0.0197(4) Uani 1 1 d . . . C20 C 0.67113(14) 0.0761(2) 1.05523(7) 0.0199(4) Uani 1 1 d . . . C21 C 0.25084(14) 0.2663(3) 1.07713(7) 0.0226(4) Uani 1 1 d . . . C22 C 0.17847(14) 0.3389(3) 1.03929(7) 0.0234(4) Uani 1 1 d . . . C23 C 0.08215(15) 0.3383(3) 1.04693(8) 0.0275(4) Uani 1 1 d . . . H7 H 0.0338 0.3837 1.0212 0.033 Uiso 1 1 calc R . . C24 C 0.05697(15) 0.2701(3) 1.09299(8) 0.0307(5) Uani 1 1 d . . . H8 H -0.0088 0.2695 1.0986 0.037 Uiso 1 1 calc R . . C25 C 0.12688(16) 0.2037(3) 1.13028(8) 0.0290(5) Uani 1 1 d . . . H9 H 0.1088 0.1591 1.1616 0.035 Uiso 1 1 calc R . . C26 C 0.22427(15) 0.2011(3) 1.12273(8) 0.0258(4) Uani 1 1 d . . . H10 H 0.2719 0.1549 1.1487 0.031 Uiso 1 1 calc R . . C27 C 0.25476(13) 0.5288(3) 0.83656(7) 0.0212(4) Uani 1 1 d . . . C28 C 0.23677(14) 0.4306(3) 0.79139(7) 0.0248(4) Uani 1 1 d . . . H11 H 0.2778 0.3385 0.7871 0.030 Uiso 1 1 calc R . . C29 C 0.15986(15) 0.4661(3) 0.75276(8) 0.0282(4) Uani 1 1 d . . . H12 H 0.1481 0.3976 0.7225 0.034 Uiso 1 1 calc R . . C30 C 0.10022(14) 0.6010(3) 0.75813(8) 0.0271(4) Uani 1 1 d . . . H13 H 0.0474 0.6250 0.7317 0.033 Uiso 1 1 calc R . . C31 C 0.11786(15) 0.7008(3) 0.80215(8) 0.0284(4) Uani 1 1 d . . . H14 H 0.0778 0.7947 0.8057 0.034 Uiso 1 1 calc R . . C32 C 0.19415(14) 0.6639(3) 0.84124(8) 0.0244(4) Uani 1 1 d . . . H15 H 0.2050 0.7321 0.8716 0.029 Uiso 1 1 calc R . . C33 C 0.73962(13) 0.2927(2) 0.83995(7) 0.0196(4) Uani 1 1 d . . . C34 C 0.82620(13) 0.3805(3) 0.84755(7) 0.0214(4) Uani 1 1 d . . . H16 H 0.8425 0.4446 0.8785 0.026 Uiso 1 1 calc R . . C35 C 0.88953(14) 0.3757(3) 0.81039(7) 0.0241(4) Uani 1 1 d . . . H17 H 0.9480 0.4381 0.8157 0.029 Uiso 1 1 calc R . . C36 C 0.86692(15) 0.2796(3) 0.76580(8) 0.0266(4) Uani 1 1 d . . . H18 H 0.9101 0.2750 0.7406 0.032 Uiso 1 1 calc R . . C37 C 0.78134(15) 0.1905(3) 0.75808(8) 0.0268(4) Uani 1 1 d . . . H19 H 0.7663 0.1236 0.7277 0.032 Uiso 1 1 calc R . . C38 C 0.71715(14) 0.1979(3) 0.79452(7) 0.0229(4) Uani 1 1 d . . . H20 H 0.6578 0.1383 0.7885 0.028 Uiso 1 1 calc R . . C39 C 0.76146(14) -0.0113(3) 1.07822(7) 0.0215(4) Uani 1 1 d . . . C40 C 0.83129(14) -0.0003(3) 1.04294(7) 0.0215(4) Uani 1 1 d . . . C41 C 0.92263(14) -0.0660(3) 1.05640(8) 0.0262(4) Uani 1 1 d . . . H21 H 0.9686 -0.0598 1.0326 0.031 Uiso 1 1 calc R . . C42 C 0.94733(15) -0.1414(3) 1.10499(8) 0.0307(5) Uani 1 1 d . . . H22 H 1.0104 -0.1861 1.1144 0.037 Uiso 1 1 calc R . . C43 C 0.88057(15) -0.1515(3) 1.13958(8) 0.0303(5) Uani 1 1 d . . . H23 H 0.8984 -0.2031 1.1726 0.036 Uiso 1 1 calc R . . C44 C 0.78693(15) -0.0868(3) 1.12656(8) 0.0253(4) Uani 1 1 d . . . H24 H 0.7414 -0.0946 1.1505 0.030 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 Zn1 0.02205(13) 0.02364(13) 0.01748(12) 0.00257(8) 0.00761(8) 0.00370(9) N1 0.0244(8) 0.0210(8) 0.0167(7) -0.0001(6) 0.0073(6) 0.0011(7) N2 0.0242(8) 0.0252(9) 0.0193(7) 0.0028(6) 0.0088(6) 0.0032(7) N3 0.0219(8) 0.0226(9) 0.0185(7) 0.0018(6) 0.0078(6) 0.0019(7) N4 0.0235(8) 0.0220(9) 0.0150(7) 0.0013(6) 0.0061(6) 0.0014(7) C1 0.0252(9) 0.0207(10) 0.0150(8) -0.0016(7) 0.0038(7) -0.0021(8) C2 0.0286(10) 0.0285(11) 0.0149(8) 0.0036(7) 0.0035(7) -0.0021(8) C3 0.0286(10) 0.0271(11) 0.0161(8) 0.0010(7) 0.0076(7) -0.0018(8) C4 0.0261(9) 0.0194(10) 0.0166(8) -0.0031(7) 0.0071(7) -0.0015(8) C5 0.0261(10) 0.0208(10) 0.0175(8) -0.0022(7) 0.0094(7) -0.0020(8) C6 0.0229(9) 0.0217(10) 0.0206(9) -0.0021(7) 0.0086(7) 0.0004(8) C7 0.0246(9) 0.0232(10) 0.0224(9) -0.0032(7) 0.0084(7) 0.0004(8) C8 0.0221(9) 0.0256(11) 0.0226(9) -0.0011(8) 0.0084(7) 0.0024(8) C9 0.0214(9) 0.0222(10) 0.0215(9) 0.0013(7) 0.0055(7) 0.0011(8) C10 0.0234(9) 0.0197(10) 0.0209(9) 0.0013(7) 0.0059(7) 0.0018(8) C11 0.0227(9) 0.0213(10) 0.0189(9) 0.0017(7) 0.0062(7) 0.0013(8) C12 0.0249(9) 0.0269(11) 0.0202(9) 0.0043(8) 0.0060(7) 0.0006(8) C13 0.0233(9) 0.0253(10) 0.0182(8) 0.0031(7) 0.0073(7) 0.0001(8) C14 0.0229(9) 0.0203(9) 0.0178(8) 0.0001(7) 0.0076(7) -0.0013(8) C15 0.0224(9) 0.0192(9) 0.0174(8) -0.0013(7) 0.0073(7) -0.0017(7) C16 0.0214(9) 0.0218(10) 0.0178(8) -0.0017(7) 0.0072(7) -0.0006(8) C17 0.0215(9) 0.0239(10) 0.0185(9) -0.0008(7) 0.0055(7) -0.0007(8) C18 0.0217(9) 0.0214(10) 0.0191(9) -0.0017(7) 0.0035(7) -0.0007(8) C19 0.0229(9) 0.0194(9) 0.0172(8) -0.0020(7) 0.0040(7) 0.0003(7) C20 0.0252(9) 0.0199(9) 0.0143(8) -0.0013(7) 0.0025(7) 0.0005(8) C21 0.0264(10) 0.0216(10) 0.0218(9) -0.0050(7) 0.0100(8) -0.0033(8) C22 0.0270(10) 0.0237(10) 0.0210(9) -0.0053(7) 0.0091(8) -0.0032(8) C23 0.0243(10) 0.0344(12) 0.0246(10) -0.0058(8) 0.0067(8) -0.0020(9) C24 0.0263(10) 0.0382(13) 0.0301(11) -0.0077(9) 0.0129(9) -0.0086(9) C25 0.0331(11) 0.0303(12) 0.0267(10) -0.0024(8) 0.0148(9) -0.0068(9) C26 0.0313(11) 0.0254(11) 0.0222(9) -0.0017(8) 0.0097(8) -0.0015(8) C27 0.0201(9) 0.0243(10) 0.0206(9) 0.0038(7) 0.0070(7) -0.0009(8) C28 0.0274(10) 0.0265(11) 0.0219(9) 0.0023(8) 0.0088(8) 0.0030(8) C29 0.0335(11) 0.0322(12) 0.0195(9) 0.0000(8) 0.0059(8) -0.0046(9) C30 0.0233(9) 0.0367(12) 0.0212(9) 0.0067(8) 0.0024(7) -0.0011(9) C31 0.0235(10) 0.0318(12) 0.0310(11) 0.0051(9) 0.0072(8) 0.0051(9) C32 0.0242(9) 0.0261(11) 0.0236(9) 0.0003(8) 0.0058(8) 0.0004(8) C33 0.0212(9) 0.0210(10) 0.0175(8) 0.0029(7) 0.0056(7) 0.0038(7) C34 0.0238(9) 0.0227(10) 0.0181(8) 0.0007(7) 0.0047(7) 0.0015(8) C35 0.0196(9) 0.0288(11) 0.0246(9) 0.0047(8) 0.0057(7) 0.0010(8) C36 0.0281(10) 0.0320(12) 0.0225(9) 0.0034(8) 0.0134(8) 0.0065(9) C37 0.0319(11) 0.0316(12) 0.0178(9) -0.0034(8) 0.0069(8) 0.0051(9) C38 0.0227(9) 0.0264(11) 0.0202(9) -0.0002(7) 0.0046(7) -0.0008(8) C39 0.0234(9) 0.0204(10) 0.0205(9) -0.0031(7) 0.0019(7) -0.0022(8) C40 0.0251(9) 0.0203(10) 0.0190(9) -0.0009(7) 0.0027(7) -0.0034(8) C41 0.0218(9) 0.0310(11) 0.0259(10) 0.0045(8) 0.0038(8) -0.0021(8) C42 0.0213(10) 0.0378(13) 0.0318(11) 0.0080(9) -0.0006(8) 0.0004(9) C43 0.0292(10) 0.0355(12) 0.0250(10) 0.0086(9) -0.0004(8) -0.0014(9) C44 0.0273(10) 0.0275(11) 0.0213(9) 0.0037(8) 0.0038(8) -0.0014(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 Zn1 N4 1.9503(16) . ? Zn1 N2 1.9620(16) . ? Zn1 N3 2.0768(15) . ? Zn1 N1 2.1372(16) . ? N1 C1 1.372(2) . ? N1 C4 1.378(2) . ? N2 C6 1.350(2) . ? N2 C9 1.389(2) . ? N3 C11 1.366(2) . ? N3 C14 1.382(2) . ? N4 C19 1.339(2) . ? N4 C16 1.388(2) . ? C1 C20 1.397(3) . ? C1 C2 1.448(2) . ? C2 C3 1.346(3) . ? C3 C4 1.450(3) . ? C4 C5 1.394(3) . ? C5 C6 1.409(3) . ? C5 C21 1.499(3) . ? C6 C7 1.424(3) . ? C7 C8 1.363(3) . ? C7 C22 1.473(3) . ? C8 C9 1.467(2) . ? C9 C10 1.404(2) . ? C10 C11 1.427(3) . ? C10 C27 1.496(3) . ? C11 C12 1.439(2) . ? C12 C13 1.357(3) . ? C13 C14 1.437(2) . ? C14 C15 1.415(3) . ? C15 C16 1.402(3) . ? C15 C33 1.501(2) . ? C16 C17 1.461(3) . ? C17 C18 1.367(3) . ? C18 C19 1.431(3) . ? C18 C40 1.468(3) . ? C19 C20 1.405(2) . ? C20 C39 1.490(3) . ? C21 C26 1.387(3) . ? C21 C22 1.427(3) . ? C22 C23 1.386(3) . ? C23 C24 1.400(3) . ? C24 C25 1.377(3) . ? C25 C26 1.401(3) . ? C27 C32 1.390(3) . ? C27 C28 1.401(3) . ? C28 C29 1.388(3) . ? C29 C30 1.384(3) . ? C30 C31 1.384(3) . ? C31 C32 1.392(3) . ? C33 C34 1.388(3) . ? C33 C38 1.397(3) . ? C34 C35 1.395(3) . ? C35 C36 1.385(3) . ? C36 C37 1.382(3) . ? C37 C38 1.390(3) . ? C39 C44 1.388(3) . ? C39 C40 1.429(3) . ? C40 C41 1.378(3) . ? C41 C42 1.392(3) . ? C42 C43 1.382(3) . ? C43 C44 1.402(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Zn1 N2 176.48(7) . . ? N4 Zn1 N3 88.41(6) . . ? N2 Zn1 N3 88.44(6) . . ? N4 Zn1 N1 91.55(6) . . ? N2 Zn1 N1 91.75(6) . . ? N3 Zn1 N1 173.70(7) . . ? C1 N1 C4 106.66(15) . . ? C1 N1 Zn1 126.34(12) . . ? C4 N1 Zn1 126.63(13) . . ? C6 N2 C9 105.25(15) . . ? C6 N2 Zn1 121.22(13) . . ? C9 N2 Zn1 130.88(12) . . ? C11 N3 C14 106.90(15) . . ? C11 N3 Zn1 126.87(12) . . ? C14 N3 Zn1 126.20(13) . . ? C19 N4 C16 105.72(16) . . ? C19 N4 Zn1 121.85(12) . . ? C16 N4 Zn1 132.39(13) . . ? N1 C1 C20 121.88(17) . . ? N1 C1 C2 109.53(16) . . ? C20 C1 C2 128.59(18) . . ? C3 C2 C1 107.31(17) . . ? C2 C3 C4 107.17(16) . . ? N1 C4 C5 121.60(17) . . ? N1 C4 C3 109.31(17) . . ? C5 C4 C3 129.00(17) . . ? C4 C5 C6 123.89(17) . . ? C4 C5 C21 130.95(18) . . ? C6 C5 C21 104.51(17) . . ? N2 C6 C5 134.58(18) . . ? N2 C6 C7 112.60(17) . . ? C5 C6 C7 112.41(17) . . ? C8 C7 C6 106.49(16) . . ? C8 C7 C22 146.40(19) . . ? C6 C7 C22 106.60(17) . . ? C7 C8 C9 106.19(17) . . ? N2 C9 C10 123.44(16) . . ? N2 C9 C8 109.42(16) . . ? C10 C9 C8 126.81(17) . . ? C9 C10 C11 124.25(17) . . ? C9 C10 C27 118.49(16) . . ? C11 C10 C27 116.97(16) . . ? N3 C11 C10 125.04(16) . . ? N3 C11 C12 109.53(15) . . ? C10 C11 C12 125.39(17) . . ? C13 C12 C11 107.19(17) . . ? C12 C13 C14 107.22(16) . . ? N3 C14 C15 125.41(16) . . ? N3 C14 C13 109.15(16) . . ? C15 C14 C13 125.45(16) . . ? C16 C15 C14 124.90(16) . . ? C16 C15 C33 117.75(17) . . ? C14 C15 C33 117.32(16) . . ? N4 C16 C15 122.57(17) . . ? N4 C16 C17 109.30(16) . . ? C15 C16 C17 128.03(17) . . ? C18 C17 C16 106.30(16) . . ? C17 C18 C19 106.12(17) . . ? C17 C18 C40 147.65(18) . . ? C19 C18 C40 106.18(16) . . ? N4 C19 C20 134.79(18) . . ? N4 C19 C18 112.54(16) . . ? C20 C19 C18 112.56(17) . . ? C1 C20 C19 123.24(17) . . ? C1 C20 C39 132.19(17) . . ? C19 C20 C39 104.57(16) . . ? C26 C21 C22 119.18(18) . . ? C26 C21 C5 131.50(19) . . ? C22 C21 C5 109.25(16) . . ? C23 C22 C21 120.51(18) . . ? C23 C22 C7 132.29(19) . . ? C21 C22 C7 107.11(17) . . ? C22 C23 C24 119.2(2) . . ? C25 C24 C23 120.51(19) . . ? C24 C25 C26 120.90(19) . . ? C21 C26 C25 119.6(2) . . ? C32 C27 C28 118.10(18) . . ? C32 C27 C10 122.34(18) . . ? C28 C27 C10 119.51(18) . . ? C29 C28 C27 120.87(19) . . ? C30 C29 C28 120.21(19) . . ? C31 C30 C29 119.67(19) . . ? C30 C31 C32 120.1(2) . . ? C27 C32 C31 120.99(19) . . ? C34 C33 C38 118.82(17) . . ? C34 C33 C15 120.71(17) . . ? C38 C33 C15 120.47(17) . . ? C33 C34 C35 120.84(18) . . ? C36 C35 C34 119.75(19) . . ? C37 C36 C35 119.88(18) . . ? C36 C37 C38 120.45(19) . . ? C37 C38 C33 120.22(19) . . ? C44 C39 C40 119.36(18) . . ? C44 C39 C20 131.15(18) . . ? C40 C39 C20 109.37(16) . . ? C41 C40 C39 120.39(18) . . ? C41 C40 C18 132.31(18) . . ? C39 C40 C18 107.26(17) . . ? C40 C41 C42 119.71(18) . . ? C43 C42 C41 120.4(2) . . ? C42 C43 C44 120.94(19) . . ? C39 C44 C43 119.23(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Zn1 N1 C1 -4.11(16) . . . . ? N2 Zn1 N1 C1 177.13(16) . . . . ? N3 Zn1 N1 C1 85.5(6) . . . . ? N4 Zn1 N1 C4 -176.22(16) . . . . ? N2 Zn1 N1 C4 5.02(17) . . . . ? N3 Zn1 N1 C4 -86.6(6) . . . . ? N4 Zn1 N2 C6 -164.7(11) . . . . ? N3 Zn1 N2 C6 168.52(16) . . . . ? N1 Zn1 N2 C6 -5.19(16) . . . . ? N4 Zn1 N2 C9 36.7(12) . . . . ? N3 Zn1 N2 C9 9.86(19) . . . . ? N1 Zn1 N2 C9 -163.84(18) . . . . ? N4 Zn1 N3 C11 179.70(17) . . . . ? N2 Zn1 N3 C11 -1.89(17) . . . . ? N1 Zn1 N3 C11 89.9(6) . . . . ? N4 Zn1 N3 C14 -3.02(17) . . . . ? N2 Zn1 N3 C14 175.39(17) . . . . ? N1 Zn1 N3 C14 -92.8(6) . . . . ? N2 Zn1 N4 C19 158.5(11) . . . . ? N3 Zn1 N4 C19 -174.68(16) . . . . ? N1 Zn1 N4 C19 -0.98(16) . . . . ? N2 Zn1 N4 C16 -24.2(12) . . . . ? N3 Zn1 N4 C16 2.59(18) . . . . ? N1 Zn1 N4 C16 176.30(18) . . . . ? C4 N1 C1 C20 -179.41(18) . . . . ? Zn1 N1 C1 C20 7.2(3) . . . . ? C4 N1 C1 C2 1.1(2) . . . . ? Zn1 N1 C1 C2 -172.31(13) . . . . ? N1 C1 C2 C3 -1.0(2) . . . . ? C20 C1 C2 C3 179.5(2) . . . . ? C1 C2 C3 C4 0.5(2) . . . . ? C1 N1 C4 C5 -177.61(18) . . . . ? Zn1 N1 C4 C5 -4.2(3) . . . . ? C1 N1 C4 C3 -0.8(2) . . . . ? Zn1 N1 C4 C3 172.59(13) . . . . ? C2 C3 C4 N1 0.2(2) . . . . ? C2 C3 C4 C5 176.7(2) . . . . ? N1 C4 C5 C6 2.5(3) . . . . ? C3 C4 C5 C6 -173.6(2) . . . . ? N1 C4 C5 C21 171.72(19) . . . . ? C3 C4 C5 C21 -4.4(4) . . . . ? C9 N2 C6 C5 169.5(2) . . . . ? Zn1 N2 C6 C5 6.1(3) . . . . ? C9 N2 C6 C7 -2.5(2) . . . . ? Zn1 N2 C6 C7 -165.89(14) . . . . ? C4 C5 C6 N2 -3.8(4) . . . . ? C21 C5 C6 N2 -175.4(2) . . . . ? C4 C5 C6 C7 168.19(19) . . . . ? C21 C5 C6 C7 -3.4(2) . . . . ? N2 C6 C7 C8 1.9(2) . . . . ? C5 C6 C7 C8 -171.90(18) . . . . ? N2 C6 C7 C22 175.99(17) . . . . ? C5 C6 C7 C22 2.2(2) . . . . ? C6 C7 C8 C9 -0.5(2) . . . . ? C22 C7 C8 C9 -170.2(3) . . . . ? C6 N2 C9 C10 -171.73(19) . . . . ? Zn1 N2 C9 C10 -10.6(3) . . . . ? C6 N2 C9 C8 2.1(2) . . . . ? Zn1 N2 C9 C8 163.25(15) . . . . ? C7 C8 C9 N2 -1.0(2) . . . . ? C7 C8 C9 C10 172.6(2) . . . . ? N2 C9 C10 C11 0.0(3) . . . . ? C8 C9 C10 C11 -172.6(2) . . . . ? N2 C9 C10 C27 173.67(18) . . . . ? C8 C9 C10 C27 1.0(3) . . . . ? C14 N3 C11 C10 176.53(19) . . . . ? Zn1 N3 C11 C10 -5.8(3) . . . . ? C14 N3 C11 C12 -1.4(2) . . . . ? Zn1 N3 C11 C12 176.33(14) . . . . ? C9 C10 C11 N3 8.1(3) . . . . ? C27 C10 C11 N3 -165.62(19) . . . . ? C9 C10 C11 C12 -174.3(2) . . . . ? C27 C10 C11 C12 12.0(3) . . . . ? N3 C11 C12 C13 0.8(2) . . . . ? C10 C11 C12 C13 -177.1(2) . . . . ? C11 C12 C13 C14 0.1(2) . . . . ? C11 N3 C14 C15 -178.65(19) . . . . ? Zn1 N3 C14 C15 3.6(3) . . . . ? C11 N3 C14 C13 1.4(2) . . . . ? Zn1 N3 C14 C13 -176.31(13) . . . . ? C12 C13 C14 N3 -0.9(2) . . . . ? C12 C13 C14 C15 179.14(19) . . . . ? N3 C14 C15 C16 -2.6(3) . . . . ? C13 C14 C15 C16 177.31(19) . . . . ? N3 C14 C15 C33 175.53(18) . . . . ? C13 C14 C15 C33 -4.5(3) . . . . ? C19 N4 C16 C15 175.11(18) . . . . ? Zn1 N4 C16 C15 -2.5(3) . . . . ? C19 N4 C16 C17 -1.5(2) . . . . ? Zn1 N4 C16 C17 -179.13(14) . . . . ? C14 C15 C16 N4 1.8(3) . . . . ? C33 C15 C16 N4 -176.30(18) . . . . ? C14 C15 C16 C17 177.81(19) . . . . ? C33 C15 C16 C17 -0.3(3) . . . . ? N4 C16 C17 C18 0.8(2) . . . . ? C15 C16 C17 C18 -175.6(2) . . . . ? C16 C17 C18 C19 0.2(2) . . . . ? C16 C17 C18 C40 177.0(3) . . . . ? C16 N4 C19 C20 -174.1(2) . . . . ? Zn1 N4 C19 C20 3.8(3) . . . . ? C16 N4 C19 C18 1.7(2) . . . . ? Zn1 N4 C19 C18 179.64(13) . . . . ? C17 C18 C19 N4 -1.3(2) . . . . ? C40 C18 C19 N4 -179.47(16) . . . . ? C17 C18 C19 C20 175.53(17) . . . . ? C40 C18 C19 C20 -2.7(2) . . . . ? N1 C1 C20 C19 -4.7(3) . . . . ? C2 C1 C20 C19 174.68(19) . . . . ? N1 C1 C20 C39 176.09(19) . . . . ? C2 C1 C20 C39 -4.5(4) . . . . ? N4 C19 C20 C1 -1.3(4) . . . . ? C18 C19 C20 C1 -177.17(18) . . . . ? N4 C19 C20 C39 178.0(2) . . . . ? C18 C19 C20 C39 2.2(2) . . . . ? C4 C5 C21 C26 9.5(4) . . . . ? C6 C5 C21 C26 -179.7(2) . . . . ? C4 C5 C21 C22 -167.4(2) . . . . ? C6 C5 C21 C22 3.4(2) . . . . ? C26 C21 C22 C23 -2.6(3) . . . . ? C5 C21 C22 C23 174.70(19) . . . . ? C26 C21 C22 C7 -179.48(18) . . . . ? C5 C21 C22 C7 -2.2(2) . . . . ? C8 C7 C22 C23 -6.5(5) . . . . ? C6 C7 C22 C23 -176.3(2) . . . . ? C8 C7 C22 C21 169.8(3) . . . . ? C6 C7 C22 C21 0.1(2) . . . . ? C21 C22 C23 C24 1.9(3) . . . . ? C7 C22 C23 C24 177.9(2) . . . . ? C22 C23 C24 C25 -0.2(3) . . . . ? C23 C24 C25 C26 -0.8(3) . . . . ? C22 C21 C26 C25 1.6(3) . . . . ? C5 C21 C26 C25 -175.0(2) . . . . ? C24 C25 C26 C21 0.1(3) . . . . ? C9 C10 C27 C32 56.2(3) . . . . ? C11 C10 C27 C32 -129.7(2) . . . . ? C9 C10 C27 C28 -121.2(2) . . . . ? C11 C10 C27 C28 52.9(3) . . . . ? C32 C27 C28 C29 -0.8(3) . . . . ? C10 C27 C28 C29 176.71(18) . . . . ? C27 C28 C29 C30 0.7(3) . . . . ? C28 C29 C30 C31 0.2(3) . . . . ? C29 C30 C31 C32 -1.1(3) . . . . ? C28 C27 C32 C31 -0.1(3) . . . . ? C10 C27 C32 C31 -177.54(18) . . . . ? C30 C31 C32 C27 1.1(3) . . . . ? C16 C15 C33 C34 -65.9(2) . . . . ? C14 C15 C33 C34 115.8(2) . . . . ? C16 C15 C33 C38 114.6(2) . . . . ? C14 C15 C33 C38 -63.7(3) . . . . ? C38 C33 C34 C35 0.5(3) . . . . ? C15 C33 C34 C35 -179.00(18) . . . . ? C33 C34 C35 C36 -1.3(3) . . . . ? C34 C35 C36 C37 0.7(3) . . . . ? C35 C36 C37 C38 0.7(3) . . . . ? C36 C37 C38 C33 -1.5(3) . . . . ? C34 C33 C38 C37 0.8(3) . . . . ? C15 C33 C38 C37 -179.60(18) . . . . ? C1 C20 C39 C44 -5.7(4) . . . . ? C19 C20 C39 C44 175.0(2) . . . . ? C1 C20 C39 C40 178.4(2) . . . . ? C19 C20 C39 C40 -0.9(2) . . . . ? C44 C39 C40 C41 0.9(3) . . . . ? C20 C39 C40 C41 177.32(18) . . . . ? C44 C39 C40 C18 -177.13(18) . . . . ? C20 C39 C40 C18 -0.7(2) . . . . ? C17 C18 C40 C41 7.5(5) . . . . ? C19 C18 C40 C41 -175.7(2) . . . . ? C17 C18 C40 C39 -174.8(3) . . . . ? C19 C18 C40 C39 2.0(2) . . . . ? C39 C40 C41 C42 -0.9(3) . . . . ? C18 C40 C41 C42 176.5(2) . . . . ? C40 C41 C42 C43 0.4(4) . . . . ? C41 C42 C43 C44 0.1(4) . . . . ? C40 C39 C44 C43 -0.3(3) . . . . ? C20 C39 C44 C43 -175.9(2) . . . . ? C42 C43 C44 C39 -0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.601 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 929176' ####################################################################### # # 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_gusa4 #TrackingRef 'web_deposit_cif_file_2_TomoyaIshizuka_1363175702.triply-fused.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H22 N4 Zn' _chemical_formula_weight 672.03 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' Zn Zn 0.2839 1.4301 '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 1 21/c 1' 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 8.010(4) _cell_length_b 13.436(6) _cell_length_c 26.359(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.647(6) _cell_angle_gamma 90.00 _cell_volume 2812(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.919 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7333 _exptl_absorpt_correction_T_max 0.9730 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 14366 _diffrn_reflns_av_R_equivalents 0.0946 _diffrn_reflns_av_sigmaI/netI 0.1366 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 27.08 _reflns_number_total 6011 _reflns_number_gt 3447 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0338P)^2^+10.0972P] 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 6011 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1588 _refine_ls_R_factor_gt 0.0814 _refine_ls_wR_factor_ref 0.1760 _refine_ls_wR_factor_gt 0.1467 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Zn1 Zn 0.64285(9) 0.11288(5) 0.95302(3) 0.0269(2) Uani 1 1 d . . . N1 N 0.6003(6) -0.0483(3) 0.94644(16) 0.0228(11) Uani 1 1 d . . . N2 N 0.7927(6) 0.0856(3) 1.01258(17) 0.0258(12) Uani 1 1 d . . . N3 N 0.6895(6) 0.2676(4) 0.96435(18) 0.0255(11) Uani 1 1 d . . . N4 N 0.4966(6) 0.1404(3) 0.89279(17) 0.0242(11) Uani 1 1 d . . . C1 C 0.4917(7) -0.0938(4) 0.9088(2) 0.0221(13) Uani 1 1 d . . . C2 C 0.4916(8) -0.2002(4) 0.9184(2) 0.0243(13) Uani 1 1 d . . . H2 H 0.4276 -0.2488 0.8980 0.029 Uiso 1 1 calc R . . C3 C 0.5981(7) -0.2174(4) 0.9610(2) 0.0238(14) Uani 1 1 d . . . H3 H 0.6224 -0.2803 0.9766 0.029 Uiso 1 1 calc R . . C4 C 0.6700(7) -0.1225(4) 0.97902(19) 0.0218(12) Uani 1 1 d . . . C5 C 0.7886(7) -0.0993(4) 1.0217(2) 0.0231(13) Uani 1 1 d . . . C6 C 0.8399(8) -0.0023(4) 1.0339(2) 0.0258(14) Uani 1 1 d . . . C7 C 0.9631(7) 0.0070(4) 1.0783(2) 0.0238(13) Uani 1 1 d . . . C8 C 0.9934(7) 0.1078(5) 1.0841(2) 0.0274(14) Uani 1 1 d . . . C9 C 0.8853(7) 0.1534(4) 1.0427(2) 0.0256(14) Uani 1 1 d . . . C10 C 0.8954(7) 0.2568(4) 1.0405(2) 0.0248(14) Uani 1 1 d . . . C11 C 0.7982(8) 0.3137(4) 1.0020(2) 0.0274(14) Uani 1 1 d . . . C12 C 0.7878(8) 0.4195(4) 0.9932(2) 0.0315(15) Uani 1 1 d . . . H12 H 0.8463 0.4693 1.0141 0.038 Uiso 1 1 calc R . . C13 C 0.6806(8) 0.4353(4) 0.9502(2) 0.0301(15) Uani 1 1 d . . . H13 H 0.6526 0.4981 0.9348 0.036 Uiso 1 1 calc R . . C14 C 0.6156(7) 0.3405(4) 0.9313(2) 0.0254(13) Uani 1 1 d . . . C15 C 0.5050(7) 0.3220(4) 0.8861(2) 0.0252(13) Uani 1 1 d . . . C16 C 0.4471(7) 0.2286(4) 0.8677(2) 0.0254(14) Uani 1 1 d . . . C17 C 0.3249(8) 0.2058(4) 0.8232(2) 0.0274(14) Uani 1 1 d . . . H17 H 0.2713 0.2524 0.7992 0.033 Uiso 1 1 calc R . . C18 C 0.3018(7) 0.1054(4) 0.8222(2) 0.0248(13) Uani 1 1 d . . . C19 C 0.4104(7) 0.0669(4) 0.8648(2) 0.0237(13) Uani 1 1 d . . . C20 C 0.4019(7) -0.0378(4) 0.8694(2) 0.0217(13) Uani 1 1 d . . . C21 C 0.8909(8) -0.1607(4) 1.0620(2) 0.0251(14) Uani 1 1 d . . . C22 C 0.9976(8) -0.0964(4) 1.0959(2) 0.0264(14) Uani 1 1 d . . . C23 C 1.1056(7) -0.1357(5) 1.1362(2) 0.0290(15) Uani 1 1 d . . . H23 H 1.1765 -0.0932 1.1585 0.035 Uiso 1 1 calc R . . C24 C 1.1092(8) -0.2378(5) 1.1437(2) 0.0348(16) Uani 1 1 d . . . H24 H 1.1836 -0.2652 1.1712 0.042 Uiso 1 1 calc R . . C25 C 1.0065(8) -0.3005(5) 1.1117(2) 0.0334(15) Uani 1 1 d . . . H25 H 1.0103 -0.3702 1.1179 0.040 Uiso 1 1 calc R . . C26 C 0.8970(8) -0.2627(5) 1.0704(2) 0.0303(15) Uani 1 1 d . . . H26 H 0.8276 -0.3063 1.0485 0.036 Uiso 1 1 calc R . . C27 C 1.0238(8) 0.2811(5) 1.0853(2) 0.0283(14) Uani 1 1 d . . . C28 C 1.0820(8) 0.1914(4) 1.1117(2) 0.0274(14) Uani 1 1 d . . . C29 C 1.2003(8) 0.1947(5) 1.1545(2) 0.0338(16) Uani 1 1 d . . . H29 H 1.2360 0.1355 1.1724 0.041 Uiso 1 1 calc R . . C30 C 1.2671(9) 0.2874(5) 1.1710(2) 0.0400(18) Uani 1 1 d . . . H30 H 1.3505 0.2907 1.2002 0.048 Uiso 1 1 calc R . . C31 C 1.2135(8) 0.3740(5) 1.1456(2) 0.0382(16) Uani 1 1 d . . . H31 H 1.2602 0.4359 1.1577 0.046 Uiso 1 1 calc R . . C32 C 1.0918(8) 0.3717(5) 1.1026(2) 0.0349(16) Uani 1 1 d . . . H32 H 1.0559 0.4315 1.0853 0.042 Uiso 1 1 calc R . . C33 C 0.4458(7) 0.4102(4) 0.8534(2) 0.0263(14) Uani 1 1 d . . . C34 C 0.3490(8) 0.4842(4) 0.8715(2) 0.0314(15) Uani 1 1 d . . . H34 H 0.3210 0.4804 0.9053 0.038 Uiso 1 1 calc R . . C35 C 0.2922(8) 0.5645(4) 0.8402(3) 0.0345(16) Uani 1 1 d . . . H35 H 0.2254 0.6148 0.8528 0.041 Uiso 1 1 calc R . . C36 C 0.3323(8) 0.5711(5) 0.7911(2) 0.0348(16) Uani 1 1 d . . . H36 H 0.2947 0.6265 0.7702 0.042 Uiso 1 1 calc R . . C37 C 0.4259(8) 0.4985(4) 0.7724(2) 0.0318(15) Uani 1 1 d . . . H37 H 0.4529 0.5029 0.7384 0.038 Uiso 1 1 calc R . . C38 C 0.4820(8) 0.4177(4) 0.8031(2) 0.0305(15) Uani 1 1 d . . . H38 H 0.5458 0.3669 0.7896 0.037 Uiso 1 1 calc R . . C39 C 0.2780(7) -0.0676(4) 0.8250(2) 0.0242(13) Uani 1 1 d . . . C40 C 0.2127(8) 0.0182(4) 0.7970(2) 0.0250(13) Uani 1 1 d . . . C41 C 0.0925(8) 0.0100(5) 0.7552(2) 0.0299(14) Uani 1 1 d . . . H41 H 0.0516 0.0676 0.7367 0.036 Uiso 1 1 calc R . . C42 C 0.0306(8) -0.0846(4) 0.7400(2) 0.0311(15) Uani 1 1 d . . . H42 H -0.0549 -0.0909 0.7115 0.037 Uiso 1 1 calc R . . C43 C 0.0922(8) -0.1674(5) 0.7658(2) 0.0318(15) Uani 1 1 d . . . H43 H 0.0504 -0.2310 0.7545 0.038 Uiso 1 1 calc R . . C44 C 0.2156(8) -0.1609(4) 0.8083(2) 0.0299(14) Uani 1 1 d . . . H44 H 0.2570 -0.2195 0.8259 0.036 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 Zn1 0.0255(4) 0.0188(3) 0.0338(4) 0.0020(3) -0.0051(3) -0.0021(3) N1 0.023(3) 0.022(3) 0.023(2) 0.004(2) 0.000(2) -0.001(2) N2 0.029(3) 0.015(3) 0.032(3) 0.001(2) -0.002(2) -0.002(2) N3 0.019(3) 0.024(3) 0.032(3) -0.002(2) 0.000(2) -0.003(2) N4 0.023(3) 0.015(3) 0.033(3) 0.004(2) -0.002(2) 0.000(2) C1 0.022(3) 0.023(3) 0.020(3) -0.003(2) 0.000(2) -0.004(3) C2 0.027(4) 0.014(3) 0.032(3) -0.003(2) 0.003(3) -0.004(3) C3 0.026(4) 0.021(3) 0.026(3) 0.002(2) 0.007(3) -0.005(3) C4 0.019(3) 0.023(3) 0.022(3) 0.006(2) -0.001(2) -0.007(3) C5 0.024(3) 0.023(3) 0.024(3) 0.007(2) 0.008(3) 0.002(3) C6 0.024(4) 0.028(3) 0.025(3) 0.002(2) -0.001(3) -0.003(3) C7 0.021(3) 0.030(3) 0.020(3) 0.002(2) 0.000(3) -0.001(3) C8 0.021(3) 0.031(4) 0.030(3) 0.001(3) 0.001(3) -0.009(3) C9 0.023(4) 0.026(3) 0.028(3) -0.005(3) 0.005(3) -0.009(3) C10 0.022(4) 0.022(3) 0.031(3) -0.002(2) 0.005(3) -0.006(3) C11 0.028(4) 0.025(3) 0.031(3) 0.000(3) 0.009(3) -0.002(3) C12 0.036(4) 0.020(3) 0.039(4) -0.008(3) 0.006(3) -0.010(3) C13 0.030(4) 0.019(3) 0.041(4) 0.001(3) 0.002(3) 0.000(3) C14 0.024(3) 0.018(3) 0.036(3) 0.003(2) 0.009(3) -0.001(3) C15 0.021(3) 0.021(3) 0.033(3) 0.003(2) 0.004(3) 0.000(3) C16 0.019(3) 0.016(3) 0.044(4) 0.003(3) 0.010(3) 0.004(3) C17 0.027(4) 0.026(4) 0.028(3) 0.001(2) -0.001(3) -0.003(3) C18 0.028(3) 0.022(3) 0.025(3) 0.000(2) 0.003(3) 0.000(3) C19 0.022(3) 0.025(3) 0.024(3) -0.003(2) 0.000(3) 0.000(3) C20 0.021(3) 0.019(3) 0.025(3) -0.001(2) 0.003(3) 0.001(2) C21 0.026(4) 0.026(3) 0.024(3) 0.003(2) 0.007(3) 0.004(3) C22 0.029(4) 0.027(4) 0.023(3) 0.001(2) 0.003(3) -0.001(3) C23 0.022(3) 0.041(4) 0.024(3) 0.004(3) 0.003(3) 0.004(3) C24 0.028(4) 0.043(4) 0.031(3) 0.013(3) 0.000(3) 0.013(3) C25 0.037(4) 0.024(4) 0.040(4) 0.008(3) 0.007(3) 0.006(3) C26 0.030(4) 0.031(4) 0.031(3) 0.003(3) 0.007(3) -0.001(3) C27 0.025(4) 0.030(4) 0.030(3) -0.006(3) 0.006(3) -0.008(3) C28 0.025(4) 0.031(4) 0.027(3) -0.006(3) 0.006(3) -0.009(3) C29 0.035(4) 0.040(4) 0.027(3) -0.002(3) 0.005(3) -0.008(3) C30 0.031(4) 0.059(5) 0.030(3) -0.007(3) -0.001(3) -0.017(4) C31 0.040(4) 0.038(4) 0.038(4) -0.009(3) 0.010(3) -0.015(3) C32 0.039(4) 0.034(4) 0.033(3) -0.007(3) 0.008(3) -0.008(3) C33 0.022(3) 0.015(3) 0.040(4) 0.000(2) -0.001(3) -0.005(2) C34 0.030(4) 0.018(3) 0.046(4) 0.000(3) 0.003(3) -0.002(3) C35 0.032(4) 0.011(3) 0.058(4) -0.003(3) -0.005(3) 0.005(3) C36 0.031(4) 0.022(3) 0.048(4) 0.006(3) -0.008(3) -0.001(3) C37 0.030(4) 0.025(3) 0.038(4) 0.007(3) -0.007(3) -0.002(3) C38 0.022(4) 0.023(3) 0.046(4) -0.001(3) 0.000(3) -0.001(3) C39 0.022(3) 0.021(3) 0.029(3) 0.001(2) 0.002(3) -0.004(3) C40 0.027(4) 0.018(3) 0.028(3) -0.003(2) -0.004(3) 0.001(3) C41 0.030(4) 0.028(4) 0.031(3) 0.001(3) -0.001(3) 0.002(3) C42 0.028(4) 0.027(3) 0.035(3) -0.003(3) -0.007(3) -0.005(3) C43 0.036(4) 0.025(4) 0.034(3) -0.008(3) 0.001(3) -0.004(3) C44 0.033(4) 0.020(3) 0.035(3) 0.002(3) -0.002(3) -0.001(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 Zn1 N4 1.880(5) . ? Zn1 N2 1.881(5) . ? Zn1 N3 2.126(5) . ? Zn1 N1 2.196(5) . ? N1 C1 1.372(7) . ? N1 C4 1.384(7) . ? N2 C6 1.341(7) . ? N2 C9 1.362(7) . ? N3 C11 1.378(7) . ? N3 C14 1.389(7) . ? N4 C19 1.364(7) . ? N4 C16 1.390(7) . ? C1 C20 1.401(8) . ? C1 C2 1.453(7) . ? C2 C3 1.336(8) . ? C3 C4 1.453(8) . ? C4 C5 1.407(8) . ? C5 C6 1.391(8) . ? C5 C21 1.500(7) . ? C6 C7 1.433(8) . ? C7 C8 1.381(8) . ? C7 C22 1.479(8) . ? C8 C9 1.436(8) . ? C8 C28 1.470(8) . ? C9 C10 1.393(8) . ? C10 C11 1.417(8) . ? C10 C27 1.495(8) . ? C11 C12 1.441(8) . ? C12 C13 1.346(8) . ? C13 C14 1.438(8) . ? C14 C15 1.410(8) . ? C15 C16 1.402(8) . ? C15 C33 1.505(8) . ? C16 C17 1.457(8) . ? C17 C18 1.361(8) . ? C18 C19 1.423(8) . ? C18 C40 1.482(8) . ? C19 C20 1.414(8) . ? C20 C39 1.485(8) . ? C21 C26 1.387(8) . ? C21 C22 1.441(8) . ? C22 C23 1.382(8) . ? C23 C24 1.387(8) . ? C24 C25 1.382(9) . ? C25 C26 1.400(8) . ? C27 C32 1.386(8) . ? C27 C28 1.438(8) . ? C28 C29 1.373(8) . ? C29 C30 1.402(9) . ? C30 C31 1.382(9) . ? C31 C32 1.394(9) . ? C33 C34 1.384(8) . ? C33 C38 1.399(8) . ? C34 C35 1.397(8) . ? C35 C36 1.377(9) . ? C36 C37 1.363(9) . ? C37 C38 1.391(8) . ? C39 C44 1.398(8) . ? C39 C40 1.430(8) . ? C40 C41 1.369(8) . ? C41 C42 1.403(8) . ? C42 C43 1.363(8) . ? C43 C44 1.396(8) . ? 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 N4 Zn1 N2 178.9(2) . . ? N4 Zn1 N3 90.25(19) . . ? N2 Zn1 N3 89.59(19) . . ? N4 Zn1 N1 93.13(18) . . ? N2 Zn1 N1 87.05(18) . . ? N3 Zn1 N1 176.41(18) . . ? C1 N1 C4 107.0(5) . . ? C1 N1 Zn1 124.9(4) . . ? C4 N1 Zn1 128.0(4) . . ? C6 N2 C9 104.1(5) . . ? C6 N2 Zn1 129.4(4) . . ? C9 N2 Zn1 126.4(4) . . ? C11 N3 C14 108.1(5) . . ? C11 N3 Zn1 128.5(4) . . ? C14 N3 Zn1 123.3(4) . . ? C19 N4 C16 105.5(5) . . ? C19 N4 Zn1 121.9(4) . . ? C16 N4 Zn1 132.6(4) . . ? N1 C1 C20 120.7(5) . . ? N1 C1 C2 109.2(5) . . ? C20 C1 C2 130.2(5) . . ? C3 C2 C1 107.5(5) . . ? C2 C3 C4 107.8(5) . . ? N1 C4 C5 120.7(5) . . ? N1 C4 C3 108.6(5) . . ? C5 C4 C3 130.7(5) . . ? C6 C5 C4 122.7(5) . . ? C6 C5 C21 103.6(5) . . ? C4 C5 C21 133.8(5) . . ? N2 C6 C5 132.1(5) . . ? N2 C6 C7 113.0(5) . . ? C5 C6 C7 114.9(5) . . ? C8 C7 C6 105.5(5) . . ? C8 C7 C22 149.8(5) . . ? C6 C7 C22 104.7(5) . . ? C7 C8 C9 104.9(5) . . ? C7 C8 C28 150.5(6) . . ? C9 C8 C28 104.6(5) . . ? N2 C9 C10 132.3(6) . . ? N2 C9 C8 112.5(5) . . ? C10 C9 C8 115.2(5) . . ? C9 C10 C11 122.6(5) . . ? C9 C10 C27 102.8(5) . . ? C11 C10 C27 134.6(5) . . ? N3 C11 C10 120.5(5) . . ? N3 C11 C12 108.1(5) . . ? C10 C11 C12 131.4(6) . . ? C13 C12 C11 107.9(5) . . ? C12 C13 C14 108.2(5) . . ? N3 C14 C15 124.9(5) . . ? N3 C14 C13 107.7(5) . . ? C15 C14 C13 127.3(5) . . ? C16 C15 C14 126.4(5) . . ? C16 C15 C33 116.2(5) . . ? C14 C15 C33 117.4(5) . . ? N4 C16 C15 122.5(5) . . ? N4 C16 C17 108.8(5) . . ? C15 C16 C17 128.6(5) . . ? C18 C17 C16 107.4(5) . . ? C17 C18 C19 106.2(5) . . ? C17 C18 C40 148.0(6) . . ? C19 C18 C40 105.8(5) . . ? N4 C19 C20 134.5(5) . . ? N4 C19 C18 112.0(5) . . ? C20 C19 C18 113.5(5) . . ? C1 C20 C19 124.9(5) . . ? C1 C20 C39 131.5(5) . . ? C19 C20 C39 103.6(5) . . ? C26 C21 C22 119.2(5) . . ? C26 C21 C5 131.4(6) . . ? C22 C21 C5 109.4(5) . . ? C23 C22 C21 120.5(6) . . ? C23 C22 C7 132.2(6) . . ? C21 C22 C7 107.3(5) . . ? C22 C23 C24 119.1(6) . . ? C25 C24 C23 121.2(6) . . ? C24 C25 C26 120.9(6) . . ? C21 C26 C25 119.2(6) . . ? C32 C27 C28 119.2(6) . . ? C32 C27 C10 130.6(6) . . ? C28 C27 C10 110.2(5) . . ? C29 C28 C27 121.0(5) . . ? C29 C28 C8 131.8(6) . . ? C27 C28 C8 107.2(5) . . ? C28 C29 C30 118.5(6) . . ? C31 C30 C29 121.1(6) . . ? C30 C31 C32 120.9(6) . . ? C27 C32 C31 119.3(6) . . ? C34 C33 C38 118.1(5) . . ? C34 C33 C15 121.2(5) . . ? C38 C33 C15 120.7(5) . . ? C33 C34 C35 120.3(6) . . ? C36 C35 C34 120.5(6) . . ? C37 C36 C35 120.1(6) . . ? C36 C37 C38 119.9(6) . . ? C37 C38 C33 121.1(6) . . ? C44 C39 C40 118.0(5) . . ? C44 C39 C20 131.6(5) . . ? C40 C39 C20 110.4(5) . . ? C41 C40 C39 121.4(5) . . ? C41 C40 C18 132.0(5) . . ? C39 C40 C18 106.6(5) . . ? C40 C41 C42 119.2(6) . . ? C43 C42 C41 120.4(6) . . ? C42 C43 C44 121.4(6) . . ? C43 C44 C39 119.7(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Zn1 N1 C1 -2.5(5) . . . . ? N2 Zn1 N1 C1 178.6(5) . . . . ? N3 Zn1 N1 C1 158(3) . . . . ? N4 Zn1 N1 C4 180.0(5) . . . . ? N2 Zn1 N1 C4 1.0(5) . . . . ? N3 Zn1 N1 C4 -20(3) . . . . ? N4 Zn1 N2 C6 -98(11) . . . . ? N3 Zn1 N2 C6 -179.1(5) . . . . ? N1 Zn1 N2 C6 2.2(5) . . . . ? N4 Zn1 N2 C9 79(11) . . . . ? N3 Zn1 N2 C9 -2.6(5) . . . . ? N1 Zn1 N2 C9 178.7(5) . . . . ? N4 Zn1 N3 C11 -176.5(5) . . . . ? N2 Zn1 N3 C11 2.4(5) . . . . ? N1 Zn1 N3 C11 23(3) . . . . ? N4 Zn1 N3 C14 0.2(5) . . . . ? N2 Zn1 N3 C14 179.1(5) . . . . ? N1 Zn1 N3 C14 -160(3) . . . . ? N2 Zn1 N4 C19 101(11) . . . . ? N3 Zn1 N4 C19 -177.3(5) . . . . ? N1 Zn1 N4 C19 1.5(5) . . . . ? N2 Zn1 N4 C16 -81(11) . . . . ? N3 Zn1 N4 C16 0.9(5) . . . . ? N1 Zn1 N4 C16 179.7(5) . . . . ? C4 N1 C1 C20 -179.5(5) . . . . ? Zn1 N1 C1 C20 2.5(8) . . . . ? C4 N1 C1 C2 0.6(6) . . . . ? Zn1 N1 C1 C2 -177.4(4) . . . . ? N1 C1 C2 C3 0.1(7) . . . . ? C20 C1 C2 C3 -179.8(6) . . . . ? C1 C2 C3 C4 -0.8(7) . . . . ? C1 N1 C4 C5 179.5(5) . . . . ? Zn1 N1 C4 C5 -2.6(8) . . . . ? C1 N1 C4 C3 -1.1(6) . . . . ? Zn1 N1 C4 C3 176.8(4) . . . . ? C2 C3 C4 N1 1.2(7) . . . . ? C2 C3 C4 C5 -179.5(6) . . . . ? N1 C4 C5 C6 1.1(9) . . . . ? C3 C4 C5 C6 -178.1(6) . . . . ? N1 C4 C5 C21 -176.8(6) . . . . ? C3 C4 C5 C21 4.0(11) . . . . ? C9 N2 C6 C5 178.4(6) . . . . ? Zn1 N2 C6 C5 -4.5(10) . . . . ? C9 N2 C6 C7 0.3(7) . . . . ? Zn1 N2 C6 C7 177.4(4) . . . . ? C4 C5 C6 N2 2.6(11) . . . . ? C21 C5 C6 N2 -179.0(6) . . . . ? C4 C5 C6 C7 -179.3(5) . . . . ? C21 C5 C6 C7 -0.9(7) . . . . ? N2 C6 C7 C8 -0.4(7) . . . . ? C5 C6 C7 C8 -178.9(5) . . . . ? N2 C6 C7 C22 179.9(5) . . . . ? C5 C6 C7 C22 1.4(7) . . . . ? C6 C7 C8 C9 0.4(6) . . . . ? C22 C7 C8 C9 179.7(10) . . . . ? C6 C7 C8 C28 -179.6(10) . . . . ? C22 C7 C8 C28 0(2) . . . . ? C6 N2 C9 C10 179.2(6) . . . . ? Zn1 N2 C9 C10 1.9(10) . . . . ? C6 N2 C9 C8 -0.1(7) . . . . ? Zn1 N2 C9 C8 -177.3(4) . . . . ? C7 C8 C9 N2 -0.2(7) . . . . ? C28 C8 C9 N2 179.8(5) . . . . ? C7 C8 C9 C10 -179.6(5) . . . . ? C28 C8 C9 C10 0.4(7) . . . . ? N2 C9 C10 C11 0.4(10) . . . . ? C8 C9 C10 C11 179.6(5) . . . . ? N2 C9 C10 C27 -179.3(6) . . . . ? C8 C9 C10 C27 0.0(7) . . . . ? C14 N3 C11 C10 -178.2(5) . . . . ? Zn1 N3 C11 C10 -1.1(8) . . . . ? C14 N3 C11 C12 2.0(7) . . . . ? Zn1 N3 C11 C12 179.1(4) . . . . ? C9 C10 C11 N3 -0.7(9) . . . . ? C27 C10 C11 N3 178.8(6) . . . . ? C9 C10 C11 C12 179.0(6) . . . . ? C27 C10 C11 C12 -1.4(12) . . . . ? N3 C11 C12 C13 -2.4(7) . . . . ? C10 C11 C12 C13 177.8(6) . . . . ? C11 C12 C13 C14 1.9(7) . . . . ? C11 N3 C14 C15 175.7(6) . . . . ? Zn1 N3 C14 C15 -1.6(8) . . . . ? C11 N3 C14 C13 -0.8(6) . . . . ? Zn1 N3 C14 C13 -178.1(4) . . . . ? C12 C13 C14 N3 -0.7(7) . . . . ? C12 C13 C14 C15 -177.2(6) . . . . ? N3 C14 C15 C16 2.1(10) . . . . ? C13 C14 C15 C16 177.9(6) . . . . ? N3 C14 C15 C33 -176.3(5) . . . . ? C13 C14 C15 C33 -0.4(9) . . . . ? C19 N4 C16 C15 177.7(6) . . . . ? Zn1 N4 C16 C15 -0.7(9) . . . . ? C19 N4 C16 C17 0.6(6) . . . . ? Zn1 N4 C16 C17 -177.8(4) . . . . ? C14 C15 C16 N4 -0.9(10) . . . . ? C33 C15 C16 N4 177.5(5) . . . . ? C14 C15 C16 C17 175.6(6) . . . . ? C33 C15 C16 C17 -6.0(9) . . . . ? N4 C16 C17 C18 0.4(7) . . . . ? C15 C16 C17 C18 -176.5(6) . . . . ? C16 C17 C18 C19 -1.2(7) . . . . ? C16 C17 C18 C40 177.8(9) . . . . ? C16 N4 C19 C20 -179.5(7) . . . . ? Zn1 N4 C19 C20 -0.8(10) . . . . ? C16 N4 C19 C18 -1.3(7) . . . . ? Zn1 N4 C19 C18 177.3(4) . . . . ? C17 C18 C19 N4 1.6(7) . . . . ? C40 C18 C19 N4 -177.8(5) . . . . ? C17 C18 C19 C20 -179.9(5) . . . . ? C40 C18 C19 C20 0.7(7) . . . . ? N1 C1 C20 C19 -1.3(9) . . . . ? C2 C1 C20 C19 178.7(6) . . . . ? N1 C1 C20 C39 -179.6(6) . . . . ? C2 C1 C20 C39 0.3(11) . . . . ? N4 C19 C20 C1 0.3(11) . . . . ? C18 C19 C20 C1 -177.8(5) . . . . ? N4 C19 C20 C39 179.0(6) . . . . ? C18 C19 C20 C39 0.9(7) . . . . ? C6 C5 C21 C26 -179.9(6) . . . . ? C4 C5 C21 C26 -1.8(11) . . . . ? C6 C5 C21 C22 0.0(6) . . . . ? C4 C5 C21 C22 178.1(6) . . . . ? C26 C21 C22 C23 0.5(9) . . . . ? C5 C21 C22 C23 -179.4(5) . . . . ? C26 C21 C22 C7 -179.2(5) . . . . ? C5 C21 C22 C7 0.9(6) . . . . ? C8 C7 C22 C23 -0.4(15) . . . . ? C6 C7 C22 C23 179.0(6) . . . . ? C8 C7 C22 C21 179.3(10) . . . . ? C6 C7 C22 C21 -1.3(6) . . . . ? C21 C22 C23 C24 -0.4(9) . . . . ? C7 C22 C23 C24 179.3(6) . . . . ? C22 C23 C24 C25 -0.3(9) . . . . ? C23 C24 C25 C26 0.8(10) . . . . ? C22 C21 C26 C25 0.0(9) . . . . ? C5 C21 C26 C25 179.9(6) . . . . ? C24 C25 C26 C21 -0.6(9) . . . . ? C9 C10 C27 C32 178.1(6) . . . . ? C11 C10 C27 C32 -1.6(11) . . . . ? C9 C10 C27 C28 -0.4(6) . . . . ? C11 C10 C27 C28 180.0(6) . . . . ? C32 C27 C28 C29 1.7(9) . . . . ? C10 C27 C28 C29 -179.7(5) . . . . ? C32 C27 C28 C8 -178.0(5) . . . . ? C10 C27 C28 C8 0.6(7) . . . . ? C7 C8 C28 C29 -0.3(16) . . . . ? C9 C8 C28 C29 179.7(6) . . . . ? C7 C8 C28 C27 179.4(10) . . . . ? C9 C8 C28 C27 -0.6(6) . . . . ? C27 C28 C29 C30 -1.8(9) . . . . ? C8 C28 C29 C30 177.8(6) . . . . ? C28 C29 C30 C31 1.1(10) . . . . ? C29 C30 C31 C32 -0.3(10) . . . . ? C28 C27 C32 C31 -0.8(9) . . . . ? C10 C27 C32 C31 -179.1(6) . . . . ? C30 C31 C32 C27 0.1(10) . . . . ? C16 C15 C33 C34 117.9(6) . . . . ? C14 C15 C33 C34 -63.6(8) . . . . ? C16 C15 C33 C38 -59.7(8) . . . . ? C14 C15 C33 C38 118.9(6) . . . . ? C38 C33 C34 C35 -1.0(9) . . . . ? C15 C33 C34 C35 -178.6(6) . . . . ? C33 C34 C35 C36 -0.3(10) . . . . ? C34 C35 C36 C37 1.0(9) . . . . ? C35 C36 C37 C38 -0.4(9) . . . . ? C36 C37 C38 C33 -0.9(9) . . . . ? C34 C33 C38 C37 1.6(9) . . . . ? C15 C33 C38 C37 179.2(6) . . . . ? C1 C20 C39 C44 -1.6(11) . . . . ? C19 C20 C39 C44 179.8(7) . . . . ? C1 C20 C39 C40 176.4(6) . . . . ? C19 C20 C39 C40 -2.2(7) . . . . ? C44 C39 C40 C41 0.1(9) . . . . ? C20 C39 C40 C41 -178.1(5) . . . . ? C44 C39 C40 C18 -179.1(5) . . . . ? C20 C39 C40 C18 2.7(7) . . . . ? C17 C18 C40 C41 -0.1(15) . . . . ? C19 C18 C40 C41 178.9(6) . . . . ? C17 C18 C40 C39 179.0(9) . . . . ? C19 C18 C40 C39 -2.1(6) . . . . ? C39 C40 C41 C42 1.0(9) . . . . ? C18 C40 C41 C42 179.9(6) . . . . ? C40 C41 C42 C43 -1.6(10) . . . . ? C41 C42 C43 C44 1.2(10) . . . . ? C42 C43 C44 C39 -0.1(10) . . . . ? C40 C39 C44 C43 -0.6(9) . . . . ? C20 C39 C44 C43 177.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.08 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 1.288 _refine_diff_density_min -1.484 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 929177' ####################################################################### # # 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_gusa12 #TrackingRef '18528_web_deposit_cif_file_3_TomoyaIshizuka_1363175702.quadruply-fused.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C49 H25 N5 Zn' _chemical_formula_weight 749.11 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' Zn Zn 0.2839 1.4301 '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 1 21/c 1' 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 13.6200(15) _cell_length_b 16.3270(18) _cell_length_c 16.8358(19) _cell_angle_alpha 90.00 _cell_angle_beta 94.124(2) _cell_angle_gamma 90.00 _cell_volume 3734.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.700 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7917 _exptl_absorpt_correction_T_max 0.9333 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 19936 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0682 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 27.00 _reflns_number_total 8104 _reflns_number_gt 5273 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0565P)^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 8104 _refine_ls_number_parameters 496 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 Zn1 Zn 0.45561(2) 0.18908(2) 0.184376(19) 0.02905(11) Uani 1 1 d . . . N1 N 0.49272(16) 0.25747(13) 0.07255(13) 0.0256(5) Uani 1 1 d . . . N2 N 0.59307(15) 0.17802(13) 0.20789(13) 0.0244(5) Uani 1 1 d . . . N3 N 0.43884(16) 0.07432(13) 0.25808(13) 0.0255(5) Uani 1 1 d . . . N4 N 0.34299(17) 0.15124(15) 0.12184(14) 0.0340(6) Uani 1 1 d . . . C1 C 0.4268(2) 0.28006(16) 0.01059(16) 0.0254(6) Uani 1 1 d . . . C2 C 0.47678(19) 0.32989(16) -0.04395(16) 0.0272(6) Uani 1 1 d . . . H2 H 0.4480 0.3550 -0.0909 0.033 Uiso 1 1 calc R . . C3 C 0.5727(2) 0.33466(16) -0.01628(16) 0.0271(6) Uani 1 1 d . . . H3 H 0.6236 0.3631 -0.0405 0.032 Uiso 1 1 calc R . . C4 C 0.58261(19) 0.28855(15) 0.05667(15) 0.0234(6) Uani 1 1 d . . . C5 C 0.66768(19) 0.26831(15) 0.10607(15) 0.0232(6) Uani 1 1 d . . . C6 C 0.66598(19) 0.21636(16) 0.17189(15) 0.0238(6) Uani 1 1 d . . . C7 C 0.76291(19) 0.19101(16) 0.20360(15) 0.0234(6) Uani 1 1 d . . . C8 C 0.74617(19) 0.13318(16) 0.26097(15) 0.0240(6) Uani 1 1 d . . . C9 C 0.64055(19) 0.12642(15) 0.26073(15) 0.0237(6) Uani 1 1 d . . . C10 C 0.60877(19) 0.06390(16) 0.30918(15) 0.0246(6) Uani 1 1 d . . . C11 C 0.5100(2) 0.03664(16) 0.30657(15) 0.0252(6) Uani 1 1 d . . . C12 C 0.4674(2) -0.03206(16) 0.34560(17) 0.0296(6) Uani 1 1 d . . . H12 H 0.5006 -0.0679 0.3830 0.035 Uiso 1 1 calc R . . C13 C 0.3715(2) -0.03593(17) 0.31905(17) 0.0308(7) Uani 1 1 d . . . H13 H 0.3244 -0.0746 0.3346 0.037 Uiso 1 1 calc R . . C14 C 0.3543(2) 0.02971(16) 0.26261(16) 0.0265(6) Uani 1 1 d . . . C15 C 0.2701(2) 0.04698(16) 0.21134(16) 0.0267(6) Uani 1 1 d . . . C16 C 0.2716(2) 0.10220(17) 0.14836(17) 0.0297(6) Uani 1 1 d . . . C17 C 0.18047(19) 0.10803(16) 0.09972(16) 0.0264(6) Uani 1 1 d . . . C18 C 0.19801(19) 0.16398(17) 0.04040(16) 0.0272(6) Uani 1 1 d . . . C19 C 0.2990(2) 0.18939(17) 0.05709(16) 0.0293(6) Uani 1 1 d . . . C20 C 0.33105(19) 0.24830(16) 0.00508(15) 0.0256(6) Uani 1 1 d . . . C21 C 0.77460(19) 0.28355(16) 0.09773(15) 0.0240(6) Uani 1 1 d . . . C22 C 0.8315(2) 0.23502(16) 0.15547(15) 0.0251(6) Uani 1 1 d . . . C23 C 0.9329(2) 0.23442(17) 0.15676(16) 0.0278(6) Uani 1 1 d . . . H23 H 0.9707 0.2017 0.1944 0.033 Uiso 1 1 calc R . . C24 C 0.9796(2) 0.28284(17) 0.10165(17) 0.0304(7) Uani 1 1 d . . . H24 H 1.0494 0.2827 0.1019 0.037 Uiso 1 1 calc R . . C25 C 0.9246(2) 0.33077(17) 0.04699(16) 0.0293(6) Uani 1 1 d . . . H25 H 0.9572 0.3638 0.0106 0.035 Uiso 1 1 calc R . . C26 C 0.8219(2) 0.33129(16) 0.04463(16) 0.0276(6) Uani 1 1 d . . . H26 H 0.7849 0.3642 0.0068 0.033 Uiso 1 1 calc R . . C27 C 0.70232(19) 0.03198(16) 0.35060(16) 0.0255(6) Uani 1 1 d . . . C28 C 0.7843(2) 0.07309(16) 0.31997(15) 0.0258(6) Uani 1 1 d . . . C29 C 0.8793(2) 0.05250(17) 0.34717(16) 0.0299(6) Uani 1 1 d . . . H29 H 0.9338 0.0790 0.3261 0.036 Uiso 1 1 calc R . . C30 C 0.8946(2) -0.00763(18) 0.40585(17) 0.0357(7) Uani 1 1 d . . . H30 H 0.9598 -0.0222 0.4245 0.043 Uiso 1 1 calc R . . C31 C 0.8152(2) -0.04617(18) 0.43696(18) 0.0367(7) Uani 1 1 d . . . H31 H 0.8264 -0.0865 0.4772 0.044 Uiso 1 1 calc R . . C32 C 0.7182(2) -0.02611(17) 0.40948(17) 0.0319(7) Uani 1 1 d . . . H32 H 0.6641 -0.0524 0.4314 0.038 Uiso 1 1 calc R . . C33 C 0.16739(19) 0.01333(16) 0.20350(16) 0.0262(6) Uani 1 1 d . . . C34 C 0.1134(2) 0.05107(16) 0.13626(16) 0.0264(6) Uani 1 1 d . . . C35 C 0.01712(19) 0.03013(17) 0.11596(17) 0.0286(6) Uani 1 1 d . . . H35 H -0.0180 0.0544 0.0712 0.034 Uiso 1 1 calc R . . C36 C -0.0280(2) -0.02778(18) 0.16263(18) 0.0351(7) Uani 1 1 d . . . H36 H -0.0950 -0.0420 0.1501 0.042 Uiso 1 1 calc R . . C37 C 0.0237(2) -0.06435(18) 0.22659(18) 0.0351(7) Uani 1 1 d . . . H37 H -0.0079 -0.1045 0.2567 0.042 Uiso 1 1 calc R . . C38 C 0.1213(2) -0.04367(16) 0.24806(17) 0.0307(7) Uani 1 1 d . . . H38 H 0.1555 -0.0686 0.2929 0.037 Uiso 1 1 calc R . . C39 C 0.24267(19) 0.26262(16) -0.05156(15) 0.0247(6) Uani 1 1 d . . . C40 C 0.1633(2) 0.21130(16) -0.03007(16) 0.0260(6) Uani 1 1 d . . . C41 C 0.0737(2) 0.21306(16) -0.07271(16) 0.0278(6) Uani 1 1 d . . . H41 H 0.0212 0.1793 -0.0580 0.033 Uiso 1 1 calc R . . C42 C 0.0612(2) 0.26554(18) -0.13813(17) 0.0332(7) Uani 1 1 d . . . H42 H -0.0002 0.2666 -0.1688 0.040 Uiso 1 1 calc R . . C43 C 0.1363(2) 0.31572(18) -0.15883(17) 0.0351(7) Uani 1 1 d . . . H43 H 0.1257 0.3518 -0.2029 0.042 Uiso 1 1 calc R . . C44 C 0.2284(2) 0.31427(17) -0.11573(16) 0.0296(6) Uani 1 1 d . . . H44 H 0.2803 0.3486 -0.1308 0.036 Uiso 1 1 calc R . . C45 C 0.3045(2) 0.3085(2) 0.2334(2) 0.0430(8) Uani 1 1 d . . . H45 H 0.2653 0.2798 0.1936 0.052 Uiso 1 1 calc R . . C46 C 0.2626(3) 0.3723(2) 0.2709(2) 0.0524(9) Uani 1 1 d . . . H46 H 0.1960 0.3873 0.2576 0.063 Uiso 1 1 calc R . . C47 C 0.3179(3) 0.4137(2) 0.3271(2) 0.0584(10) Uani 1 1 d . . . H47 H 0.2906 0.4587 0.3538 0.070 Uiso 1 1 calc R . . C48 C 0.4139(3) 0.3905(3) 0.3460(2) 0.0707(12) Uani 1 1 d . . . H48 H 0.4539 0.4187 0.3857 0.085 Uiso 1 1 calc R . . C49 C 0.4506(3) 0.3245(2) 0.3048(2) 0.0535(9) Uani 1 1 d . . . H49 H 0.5168 0.3081 0.3173 0.064 Uiso 1 1 calc R . . N5 N 0.39805(18) 0.28368(15) 0.24939(14) 0.0337(6) 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 Zn1 0.02531(18) 0.03131(19) 0.02991(19) 0.00457(16) -0.00226(13) -0.00051(15) N1 0.0284(13) 0.0261(12) 0.0219(12) 0.0034(10) -0.0018(10) -0.0026(10) N2 0.0225(11) 0.0259(12) 0.0247(12) 0.0066(10) 0.0014(10) -0.0002(10) N3 0.0323(13) 0.0238(12) 0.0198(11) 0.0034(10) -0.0015(10) 0.0003(10) N4 0.0305(13) 0.0367(14) 0.0337(14) 0.0162(12) -0.0051(11) -0.0087(11) C1 0.0299(15) 0.0241(14) 0.0220(14) 0.0031(12) -0.0001(12) -0.0016(12) C2 0.0312(15) 0.0279(15) 0.0217(14) 0.0056(12) -0.0026(12) -0.0021(12) C3 0.0329(16) 0.0259(15) 0.0224(14) 0.0022(12) 0.0021(12) -0.0059(12) C4 0.0272(14) 0.0220(14) 0.0209(13) -0.0002(11) 0.0008(11) -0.0009(11) C5 0.0275(14) 0.0207(14) 0.0211(13) -0.0012(11) -0.0006(11) -0.0014(11) C6 0.0289(15) 0.0203(13) 0.0219(14) -0.0013(11) 0.0007(12) 0.0041(11) C7 0.0258(14) 0.0215(13) 0.0225(13) -0.0031(12) -0.0002(11) 0.0010(12) C8 0.0253(14) 0.0249(14) 0.0212(14) -0.0043(12) -0.0025(11) 0.0034(11) C9 0.0282(15) 0.0214(14) 0.0212(14) 0.0006(12) 0.0003(11) 0.0008(11) C10 0.0337(16) 0.0216(14) 0.0180(13) -0.0010(11) -0.0010(12) 0.0042(12) C11 0.0342(15) 0.0201(14) 0.0211(13) -0.0009(11) 0.0014(12) 0.0031(12) C12 0.0380(17) 0.0234(15) 0.0271(15) 0.0074(12) 0.0014(13) 0.0017(13) C13 0.0393(17) 0.0229(14) 0.0302(16) 0.0053(13) 0.0022(13) -0.0006(13) C14 0.0354(16) 0.0217(14) 0.0224(14) -0.0001(12) 0.0022(12) -0.0002(12) C15 0.0317(15) 0.0211(14) 0.0276(15) 0.0019(12) 0.0040(12) -0.0037(12) C16 0.0278(15) 0.0296(15) 0.0307(15) 0.0059(13) -0.0041(12) -0.0055(12) C17 0.0285(15) 0.0247(14) 0.0258(14) 0.0033(12) -0.0002(12) 0.0001(12) C18 0.0254(15) 0.0312(15) 0.0243(14) 0.0010(12) -0.0021(12) -0.0032(12) C19 0.0294(15) 0.0297(15) 0.0277(14) 0.0066(13) -0.0056(12) -0.0045(13) C20 0.0303(15) 0.0275(14) 0.0186(13) 0.0032(12) -0.0007(12) -0.0014(12) C21 0.0265(14) 0.0231(14) 0.0226(14) -0.0061(12) 0.0014(12) -0.0003(11) C22 0.0310(15) 0.0233(15) 0.0208(14) -0.0046(12) 0.0011(12) -0.0007(12) C23 0.0316(16) 0.0283(16) 0.0226(14) -0.0050(12) -0.0035(12) 0.0008(12) C24 0.0234(15) 0.0366(16) 0.0312(15) -0.0086(14) 0.0015(13) -0.0024(12) C25 0.0311(15) 0.0318(16) 0.0251(15) -0.0016(12) 0.0025(12) -0.0081(12) C26 0.0308(15) 0.0290(15) 0.0228(14) -0.0033(12) 0.0007(12) -0.0060(12) C27 0.0306(15) 0.0208(14) 0.0249(14) -0.0039(12) -0.0006(12) 0.0043(12) C28 0.0333(15) 0.0213(14) 0.0224(14) -0.0024(12) -0.0014(12) 0.0023(12) C29 0.0300(15) 0.0294(15) 0.0294(15) -0.0004(13) -0.0037(13) 0.0006(12) C30 0.0339(17) 0.0355(17) 0.0363(17) 0.0031(15) -0.0068(14) 0.0094(14) C31 0.0456(19) 0.0294(16) 0.0337(17) 0.0079(14) -0.0065(15) 0.0075(14) C32 0.0385(17) 0.0247(15) 0.0321(16) 0.0022(13) 0.0002(14) 0.0039(13) C33 0.0299(15) 0.0204(13) 0.0285(15) -0.0020(12) 0.0032(12) -0.0013(12) C34 0.0316(15) 0.0230(14) 0.0250(14) -0.0011(12) 0.0045(12) -0.0024(12) C35 0.0269(15) 0.0287(15) 0.0302(15) -0.0004(13) 0.0008(12) 0.0000(12) C36 0.0311(16) 0.0354(17) 0.0393(18) -0.0007(14) 0.0057(14) -0.0066(13) C37 0.0378(17) 0.0306(16) 0.0382(18) 0.0058(14) 0.0112(14) -0.0042(13) C38 0.0375(17) 0.0256(15) 0.0295(15) 0.0011(13) 0.0048(13) -0.0003(13) C39 0.0305(15) 0.0243(15) 0.0191(14) -0.0007(11) 0.0011(12) 0.0003(12) C40 0.0297(15) 0.0264(15) 0.0219(14) 0.0000(12) 0.0007(12) 0.0007(12) C41 0.0266(15) 0.0286(15) 0.0281(15) 0.0006(12) 0.0005(12) -0.0008(12) C42 0.0279(15) 0.0420(18) 0.0284(16) 0.0009(14) -0.0067(13) 0.0021(13) C43 0.0375(17) 0.0404(18) 0.0265(15) 0.0102(14) -0.0033(13) -0.0008(14) C44 0.0300(15) 0.0335(16) 0.0251(14) 0.0021(13) 0.0005(12) -0.0042(13) C45 0.0370(18) 0.050(2) 0.0429(18) 0.0135(17) 0.0079(15) 0.0130(16) C46 0.046(2) 0.060(2) 0.053(2) 0.014(2) 0.0122(18) 0.0180(18) C47 0.067(3) 0.050(2) 0.061(3) 0.004(2) 0.024(2) 0.018(2) C48 0.072(3) 0.071(3) 0.068(3) -0.027(2) -0.004(2) 0.019(2) C49 0.049(2) 0.054(2) 0.058(2) -0.0101(19) 0.0037(18) 0.0096(17) N5 0.0371(14) 0.0335(14) 0.0309(13) 0.0115(12) 0.0043(11) 0.0027(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 1.894(2) . ? Zn1 N4 1.900(2) . ? Zn1 N5 2.079(3) . ? Zn1 N3 2.268(2) . ? Zn1 N1 2.277(2) . ? N1 C4 1.369(3) . ? N1 C1 1.376(3) . ? N2 C6 1.353(3) . ? N2 C9 1.355(3) . ? N3 C11 1.368(3) . ? N3 C14 1.369(3) . ? N4 C19 1.357(3) . ? N4 C16 1.359(3) . ? C1 C20 1.401(4) . ? C1 C2 1.434(4) . ? C2 C3 1.357(4) . ? C3 C4 1.439(4) . ? C4 C5 1.416(3) . ? C5 C6 1.397(4) . ? C5 C21 1.494(4) . ? C6 C7 1.448(3) . ? C7 C8 1.381(4) . ? C7 C22 1.468(4) . ? C8 C9 1.443(4) . ? C8 C28 1.464(4) . ? C9 C10 1.395(4) . ? C10 C11 1.414(4) . ? C10 C27 1.501(3) . ? C11 C12 1.443(4) . ? C12 C13 1.352(4) . ? C13 C14 1.440(4) . ? C14 C15 1.414(4) . ? C15 C16 1.393(4) . ? C15 C33 1.499(4) . ? C16 C17 1.440(4) . ? C17 C18 1.387(4) . ? C17 C34 1.470(4) . ? C18 C19 1.445(4) . ? C18 C40 1.465(4) . ? C19 C20 1.392(4) . ? C20 C39 1.499(3) . ? C21 C26 1.380(4) . ? C21 C22 1.437(4) . ? C22 C23 1.380(4) . ? C23 C24 1.405(4) . ? C24 C25 1.386(4) . ? C25 C26 1.397(4) . ? C27 C32 1.378(4) . ? C27 C28 1.430(4) . ? C28 C29 1.383(4) . ? C29 C30 1.398(4) . ? C30 C31 1.386(4) . ? C31 C32 1.406(4) . ? C33 C38 1.375(4) . ? C33 C34 1.443(4) . ? C34 C35 1.374(4) . ? C35 C36 1.400(4) . ? C36 C37 1.379(4) . ? C37 C38 1.394(4) . ? C39 C44 1.373(4) . ? C39 C40 1.434(4) . ? C40 C41 1.371(4) . ? C41 C42 1.396(4) . ? C42 C43 1.375(4) . ? C43 C44 1.403(4) . ? C45 N5 1.345(4) . ? C45 C46 1.365(4) . ? C46 C47 1.348(5) . ? C47 C48 1.376(5) . ? C48 C49 1.394(5) . ? C49 N5 1.315(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Zn1 N4 146.22(11) . . ? N2 Zn1 N5 111.43(10) . . ? N4 Zn1 N5 102.32(11) . . ? N2 Zn1 N3 86.78(8) . . ? N4 Zn1 N3 85.73(9) . . ? N5 Zn1 N3 105.61(8) . . ? N2 Zn1 N1 86.83(8) . . ? N4 Zn1 N1 85.39(9) . . ? N5 Zn1 N1 100.70(8) . . ? N3 Zn1 N1 153.47(8) . . ? C4 N1 C1 107.2(2) . . ? C4 N1 Zn1 126.72(17) . . ? C1 N1 Zn1 125.91(17) . . ? C6 N2 C9 104.5(2) . . ? C6 N2 Zn1 127.47(17) . . ? C9 N2 Zn1 127.90(18) . . ? C11 N3 C14 106.9(2) . . ? C11 N3 Zn1 127.10(18) . . ? C14 N3 Zn1 126.03(17) . . ? C19 N4 C16 104.4(2) . . ? C19 N4 Zn1 126.02(19) . . ? C16 N4 Zn1 125.26(19) . . ? N1 C1 C20 120.3(2) . . ? N1 C1 C2 108.9(2) . . ? C20 C1 C2 130.5(2) . . ? C3 C2 C1 107.6(2) . . ? C2 C3 C4 107.0(2) . . ? N1 C4 C5 120.3(2) . . ? N1 C4 C3 109.3(2) . . ? C5 C4 C3 130.3(2) . . ? C6 C5 C4 123.2(2) . . ? C6 C5 C21 104.3(2) . . ? C4 C5 C21 131.9(2) . . ? N2 C6 C5 133.7(2) . . ? N2 C6 C7 112.4(2) . . ? C5 C6 C7 113.5(2) . . ? C8 C7 C6 105.1(2) . . ? C8 C7 C22 149.8(2) . . ? C6 C7 C22 104.8(2) . . ? C7 C8 C9 105.4(2) . . ? C7 C8 C28 149.8(3) . . ? C9 C8 C28 104.8(2) . . ? N2 C9 C10 133.3(2) . . ? N2 C9 C8 112.5(2) . . ? C10 C9 C8 113.9(2) . . ? C9 C10 C11 123.1(2) . . ? C9 C10 C27 103.7(2) . . ? C11 C10 C27 132.7(2) . . ? N3 C11 C10 120.6(2) . . ? N3 C11 C12 109.3(2) . . ? C10 C11 C12 130.0(2) . . ? C13 C12 C11 107.3(2) . . ? C12 C13 C14 106.9(2) . . ? N3 C14 C15 120.6(2) . . ? N3 C14 C13 109.6(2) . . ? C15 C14 C13 129.6(3) . . ? C16 C15 C14 122.5(2) . . ? C16 C15 C33 103.6(2) . . ? C14 C15 C33 133.8(2) . . ? N4 C16 C15 133.0(2) . . ? N4 C16 C17 112.4(2) . . ? C15 C16 C17 114.6(2) . . ? C18 C17 C16 105.5(2) . . ? C18 C17 C34 149.6(3) . . ? C16 C17 C34 104.9(2) . . ? C17 C18 C19 105.1(2) . . ? C17 C18 C40 150.3(3) . . ? C19 C18 C40 104.7(2) . . ? N4 C19 C20 133.0(3) . . ? N4 C19 C18 112.6(2) . . ? C20 C19 C18 114.4(2) . . ? C19 C20 C1 123.1(2) . . ? C19 C20 C39 103.5(2) . . ? C1 C20 C39 133.3(2) . . ? C26 C21 C22 119.7(2) . . ? C26 C21 C5 131.2(2) . . ? C22 C21 C5 109.1(2) . . ? C23 C22 C21 120.3(3) . . ? C23 C22 C7 131.6(3) . . ? C21 C22 C7 108.0(2) . . ? C22 C23 C24 119.0(3) . . ? C25 C24 C23 120.5(3) . . ? C24 C25 C26 121.0(3) . . ? C21 C26 C25 119.4(3) . . ? C32 C27 C28 119.7(2) . . ? C32 C27 C10 131.1(3) . . ? C28 C27 C10 109.1(2) . . ? C29 C28 C27 120.2(2) . . ? C29 C28 C8 131.7(3) . . ? C27 C28 C8 108.1(2) . . ? C28 C29 C30 119.6(3) . . ? C31 C30 C29 120.3(3) . . ? C30 C31 C32 120.7(3) . . ? C27 C32 C31 119.5(3) . . ? C38 C33 C34 119.3(2) . . ? C38 C33 C15 131.3(3) . . ? C34 C33 C15 109.4(2) . . ? C35 C34 C33 120.8(2) . . ? C35 C34 C17 131.6(3) . . ? C33 C34 C17 107.5(2) . . ? C34 C35 C36 118.6(3) . . ? C37 C36 C35 120.7(3) . . ? C36 C37 C38 121.4(3) . . ? C33 C38 C37 119.1(3) . . ? C44 C39 C40 119.4(2) . . ? C44 C39 C20 131.1(2) . . ? C40 C39 C20 109.5(2) . . ? C41 C40 C39 121.0(2) . . ? C41 C40 C18 131.1(3) . . ? C39 C40 C18 107.9(2) . . ? C40 C41 C42 118.6(3) . . ? C43 C42 C41 121.0(3) . . ? C42 C43 C44 120.9(3) . . ? C39 C44 C43 119.2(3) . . ? N5 C45 C46 124.0(3) . . ? C47 C46 C45 118.4(3) . . ? C46 C47 C48 119.9(3) . . ? C47 C48 C49 117.8(4) . . ? N5 C49 C48 123.3(3) . . ? C49 N5 C45 116.7(3) . . ? C49 N5 Zn1 122.9(2) . . ? C45 N5 Zn1 120.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Zn1 N1 C4 -14.4(2) . . . . ? N4 Zn1 N1 C4 -161.5(2) . . . . ? N5 Zn1 N1 C4 96.8(2) . . . . ? N3 Zn1 N1 C4 -90.7(3) . . . . ? N2 Zn1 N1 C1 170.3(2) . . . . ? N4 Zn1 N1 C1 23.2(2) . . . . ? N5 Zn1 N1 C1 -78.5(2) . . . . ? N3 Zn1 N1 C1 94.0(3) . . . . ? N4 Zn1 N2 C6 88.1(3) . . . . ? N5 Zn1 N2 C6 -89.0(2) . . . . ? N3 Zn1 N2 C6 165.5(2) . . . . ? N1 Zn1 N2 C6 11.3(2) . . . . ? N4 Zn1 N2 C9 -87.3(3) . . . . ? N5 Zn1 N2 C9 95.6(2) . . . . ? N3 Zn1 N2 C9 -9.9(2) . . . . ? N1 Zn1 N2 C9 -164.1(2) . . . . ? N2 Zn1 N3 C11 11.2(2) . . . . ? N4 Zn1 N3 C11 158.2(2) . . . . ? N5 Zn1 N3 C11 -100.2(2) . . . . ? N1 Zn1 N3 C11 87.5(3) . . . . ? N2 Zn1 N3 C14 -169.2(2) . . . . ? N4 Zn1 N3 C14 -22.2(2) . . . . ? N5 Zn1 N3 C14 79.4(2) . . . . ? N1 Zn1 N3 C14 -92.9(3) . . . . ? N2 Zn1 N4 C19 -102.3(3) . . . . ? N5 Zn1 N4 C19 75.0(3) . . . . ? N3 Zn1 N4 C19 -180.0(3) . . . . ? N1 Zn1 N4 C19 -25.0(2) . . . . ? N2 Zn1 N4 C16 104.6(3) . . . . ? N5 Zn1 N4 C16 -78.1(3) . . . . ? N3 Zn1 N4 C16 26.9(2) . . . . ? N1 Zn1 N4 C16 -178.1(2) . . . . ? C4 N1 C1 C20 171.9(2) . . . . ? Zn1 N1 C1 C20 -12.1(4) . . . . ? C4 N1 C1 C2 -2.5(3) . . . . ? Zn1 N1 C1 C2 173.48(17) . . . . ? N1 C1 C2 C3 2.1(3) . . . . ? C20 C1 C2 C3 -171.5(3) . . . . ? C1 C2 C3 C4 -0.8(3) . . . . ? C1 N1 C4 C5 -173.6(2) . . . . ? Zn1 N1 C4 C5 10.4(3) . . . . ? C1 N1 C4 C3 2.0(3) . . . . ? Zn1 N1 C4 C3 -173.95(17) . . . . ? C2 C3 C4 N1 -0.7(3) . . . . ? C2 C3 C4 C5 174.3(3) . . . . ? N1 C4 C5 C6 0.6(4) . . . . ? C3 C4 C5 C6 -174.0(3) . . . . ? N1 C4 C5 C21 170.9(3) . . . . ? C3 C4 C5 C21 -3.7(5) . . . . ? C9 N2 C6 C5 170.6(3) . . . . ? Zn1 N2 C6 C5 -5.7(4) . . . . ? C9 N2 C6 C7 -1.8(3) . . . . ? Zn1 N2 C6 C7 -178.03(17) . . . . ? C4 C5 C6 N2 -4.3(5) . . . . ? C21 C5 C6 N2 -176.9(3) . . . . ? C4 C5 C6 C7 168.0(2) . . . . ? C21 C5 C6 C7 -4.6(3) . . . . ? N2 C6 C7 C8 1.0(3) . . . . ? C5 C6 C7 C8 -173.0(2) . . . . ? N2 C6 C7 C22 177.2(2) . . . . ? C5 C6 C7 C22 3.3(3) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C22 C7 C8 C9 -172.6(4) . . . . ? C6 C7 C8 C28 176.3(4) . . . . ? C22 C7 C8 C28 3.5(8) . . . . ? C6 N2 C9 C10 -171.4(3) . . . . ? Zn1 N2 C9 C10 4.8(4) . . . . ? C6 N2 C9 C8 1.9(3) . . . . ? Zn1 N2 C9 C8 178.15(17) . . . . ? C7 C8 C9 N2 -1.4(3) . . . . ? C28 C8 C9 N2 -179.3(2) . . . . ? C7 C8 C9 C10 173.4(2) . . . . ? C28 C8 C9 C10 -4.6(3) . . . . ? N2 C9 C10 C11 5.4(5) . . . . ? C8 C9 C10 C11 -167.9(2) . . . . ? N2 C9 C10 C27 178.8(3) . . . . ? C8 C9 C10 C27 5.5(3) . . . . ? C14 N3 C11 C10 174.1(2) . . . . ? Zn1 N3 C11 C10 -6.2(3) . . . . ? C14 N3 C11 C12 -2.6(3) . . . . ? Zn1 N3 C11 C12 177.08(17) . . . . ? C9 C10 C11 N3 -3.5(4) . . . . ? C27 C10 C11 N3 -174.7(3) . . . . ? C9 C10 C11 C12 172.5(3) . . . . ? C27 C10 C11 C12 1.2(5) . . . . ? N3 C11 C12 C13 1.1(3) . . . . ? C10 C11 C12 C13 -175.2(3) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C11 N3 C14 C15 -171.9(2) . . . . ? Zn1 N3 C14 C15 8.4(4) . . . . ? C11 N3 C14 C13 3.1(3) . . . . ? Zn1 N3 C14 C13 -176.62(17) . . . . ? C12 C13 C14 N3 -2.4(3) . . . . ? C12 C13 C14 C15 172.0(3) . . . . ? N3 C14 C15 C16 7.9(4) . . . . ? C13 C14 C15 C16 -166.0(3) . . . . ? N3 C14 C15 C33 -176.8(3) . . . . ? C13 C14 C15 C33 9.4(5) . . . . ? C19 N4 C16 C15 179.0(3) . . . . ? Zn1 N4 C16 C15 -23.2(5) . . . . ? C19 N4 C16 C17 0.6(3) . . . . ? Zn1 N4 C16 C17 158.4(2) . . . . ? C14 C15 C16 N4 -2.0(5) . . . . ? C33 C15 C16 N4 -178.6(3) . . . . ? C14 C15 C16 C17 176.3(3) . . . . ? C33 C15 C16 C17 -0.2(3) . . . . ? N4 C16 C17 C18 0.0(3) . . . . ? C15 C16 C17 C18 -178.7(2) . . . . ? N4 C16 C17 C34 179.4(2) . . . . ? C15 C16 C17 C34 0.7(3) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? C34 C17 C18 C19 -179.4(4) . . . . ? C16 C17 C18 C40 -178.2(5) . . . . ? C34 C17 C18 C40 2.9(9) . . . . ? C16 N4 C19 C20 177.9(3) . . . . ? Zn1 N4 C19 C20 20.3(5) . . . . ? C16 N4 C19 C18 -0.9(3) . . . . ? Zn1 N4 C19 C18 -158.5(2) . . . . ? C17 C18 C19 N4 0.9(3) . . . . ? C40 C18 C19 N4 179.7(2) . . . . ? C17 C18 C19 C20 -178.2(2) . . . . ? C40 C18 C19 C20 0.7(3) . . . . ? N4 C19 C20 C1 2.1(5) . . . . ? C18 C19 C20 C1 -179.1(3) . . . . ? N4 C19 C20 C39 -179.1(3) . . . . ? C18 C19 C20 C39 -0.3(3) . . . . ? N1 C1 C20 C19 -4.4(4) . . . . ? C2 C1 C20 C19 168.6(3) . . . . ? N1 C1 C20 C39 177.2(3) . . . . ? C2 C1 C20 C39 -9.8(5) . . . . ? C6 C5 C21 C26 -178.5(3) . . . . ? C4 C5 C21 C26 9.8(5) . . . . ? C6 C5 C21 C22 4.2(3) . . . . ? C4 C5 C21 C22 -167.5(3) . . . . ? C26 C21 C22 C23 -1.6(4) . . . . ? C5 C21 C22 C23 176.1(2) . . . . ? C26 C21 C22 C7 180.0(2) . . . . ? C5 C21 C22 C7 -2.4(3) . . . . ? C8 C7 C22 C23 -5.8(6) . . . . ? C6 C7 C22 C23 -178.6(3) . . . . ? C8 C7 C22 C21 172.4(4) . . . . ? C6 C7 C22 C21 -0.4(3) . . . . ? C21 C22 C23 C24 1.0(4) . . . . ? C7 C22 C23 C24 179.0(3) . . . . ? C22 C23 C24 C25 0.3(4) . . . . ? C23 C24 C25 C26 -0.9(4) . . . . ? C22 C21 C26 C25 1.0(4) . . . . ? C5 C21 C26 C25 -176.1(3) . . . . ? C24 C25 C26 C21 0.2(4) . . . . ? C9 C10 C27 C32 175.2(3) . . . . ? C11 C10 C27 C32 -12.4(5) . . . . ? C9 C10 C27 C28 -4.3(3) . . . . ? C11 C10 C27 C28 168.1(3) . . . . ? C32 C27 C28 C29 2.4(4) . . . . ? C10 C27 C28 C29 -178.1(2) . . . . ? C32 C27 C28 C8 -177.8(2) . . . . ? C10 C27 C28 C8 1.7(3) . . . . ? C7 C8 C28 C29 5.2(7) . . . . ? C9 C8 C28 C29 -178.8(3) . . . . ? C7 C8 C28 C27 -174.6(4) . . . . ? C9 C8 C28 C27 1.5(3) . . . . ? C27 C28 C29 C30 -1.2(4) . . . . ? C8 C28 C29 C30 179.1(3) . . . . ? C28 C29 C30 C31 -0.3(4) . . . . ? C29 C30 C31 C32 0.7(4) . . . . ? C28 C27 C32 C31 -2.0(4) . . . . ? C10 C27 C32 C31 178.5(3) . . . . ? C30 C31 C32 C27 0.5(4) . . . . ? C16 C15 C33 C38 179.9(3) . . . . ? C14 C15 C33 C38 3.9(5) . . . . ? C16 C15 C33 C34 -0.4(3) . . . . ? C14 C15 C33 C34 -176.3(3) . . . . ? C38 C33 C34 C35 -0.6(4) . . . . ? C15 C33 C34 C35 179.5(2) . . . . ? C38 C33 C34 C17 -179.4(2) . . . . ? C15 C33 C34 C17 0.8(3) . . . . ? C18 C17 C34 C35 -0.5(7) . . . . ? C16 C17 C34 C35 -179.5(3) . . . . ? C18 C17 C34 C33 178.1(4) . . . . ? C16 C17 C34 C33 -0.9(3) . . . . ? C33 C34 C35 C36 0.9(4) . . . . ? C17 C34 C35 C36 179.3(3) . . . . ? C34 C35 C36 C37 -1.4(4) . . . . ? C35 C36 C37 C38 1.6(5) . . . . ? C34 C33 C38 C37 0.8(4) . . . . ? C15 C33 C38 C37 -179.5(3) . . . . ? C36 C37 C38 C33 -1.2(4) . . . . ? C19 C20 C39 C44 179.5(3) . . . . ? C1 C20 C39 C44 -1.8(5) . . . . ? C19 C20 C39 C40 -0.1(3) . . . . ? C1 C20 C39 C40 178.5(3) . . . . ? C44 C39 C40 C41 0.1(4) . . . . ? C20 C39 C40 C41 179.8(2) . . . . ? C44 C39 C40 C18 -179.2(2) . . . . ? C20 C39 C40 C18 0.5(3) . . . . ? C17 C18 C40 C41 -2.2(7) . . . . ? C19 C18 C40 C41 -179.9(3) . . . . ? C17 C18 C40 C39 177.0(5) . . . . ? C19 C18 C40 C39 -0.7(3) . . . . ? C39 C40 C41 C42 0.5(4) . . . . ? C18 C40 C41 C42 179.5(3) . . . . ? C40 C41 C42 C43 -1.2(4) . . . . ? C41 C42 C43 C44 1.4(5) . . . . ? C40 C39 C44 C43 0.1(4) . . . . ? C20 C39 C44 C43 -179.6(3) . . . . ? C42 C43 C44 C39 -0.8(4) . . . . ? N5 C45 C46 C47 0.4(5) . . . . ? C45 C46 C47 C48 -0.6(5) . . . . ? C46 C47 C48 C49 0.4(6) . . . . ? C47 C48 C49 N5 -0.1(6) . . . . ? C48 C49 N5 C45 -0.2(5) . . . . ? C48 C49 N5 Zn1 176.8(3) . . . . ? C46 C45 N5 C49 0.0(5) . . . . ? C46 C45 N5 Zn1 -177.0(2) . . . . ? N2 Zn1 N5 C49 -5.8(3) . . . . ? N4 Zn1 N5 C49 175.8(3) . . . . ? N3 Zn1 N5 C49 86.8(3) . . . . ? N1 Zn1 N5 C49 -96.6(3) . . . . ? N2 Zn1 N5 C45 171.0(2) . . . . ? N4 Zn1 N5 C45 -7.3(2) . . . . ? N3 Zn1 N5 C45 -96.3(2) . . . . ? N1 Zn1 N5 C45 80.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.511 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.068 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 0.500 0.500 0.500 291 78 ' ' 2 0.500 1.000 0.000 291 78 ' ' _database_code_depnum_ccdc_archive 'CCDC 929178'