# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_section_title ; Synthesis and reactivity of tetrakis(imino)pyracene (TIP) ligands; bifunctional analogues of the BIAN ligand class ; loop_ _publ_author_name _publ_author_address 'Alan H. Cowley' ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; 'Kalyan V. Vasudevan' ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; 'Michael Findlater' ; ; _publ_contact_author_address ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; _publ_contact_author_email cowley@mail.utexas.edu _publ_contact_author_fax 512-471-6822 _publ_contact_author_phone 512-471-7710 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Alan H. Cowley' _publ_contact_letter ; Please consider this CIF submission for publication in ; # Attachment 'Compound 6.cif' data_borondicat _database_code_depnum_ccdc_archive 'CCDC 670787' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _publ_section_synopsis ; ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Sluis, P. v.d. & Spek, A. L. (1990). SQUEEZE. Acta Cryst. A46, 194-201. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C62 H72 B2 Cl4 N4, 2(BCl4)' _chemical_formula_sum 'C68 H72 B2 Cl24 N4' _chemical_formula_weight 1851.41 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M p21/n _symmetry_space_group_name_Hall -p2yn 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 16.075(3) _cell_length_b 16.312(3) _cell_length_c 17.424(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.66(3) _cell_angle_gamma 90.00 _cell_volume 4377.2(15) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max .20 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1896 _exptl_absorpt_coefficient_mu 0.786 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9562 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0791 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 27.20 _reflns_number_total 9562 _reflns_number_gt 5504 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.1594P)^2^+32.6097P] 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 SHELXL _refine_ls_extinction_coef 0.0021(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9562 _refine_ls_number_parameters 461 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1873 _refine_ls_R_factor_gt 0.1189 _refine_ls_wR_factor_ref 0.3692 _refine_ls_wR_factor_gt 0.3085 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 C32 C 0.3169(9) 0.4902(9) 0.5552(8) 0.082(4) Uani 1 1 d . . . H32A H 0.2905 0.4416 0.5702 0.098 Uiso 1 1 calc R . . H32B H 0.3370 0.5245 0.6023 0.098 Uiso 1 1 calc R . . C33 C -0.0417(11) 0.5179(11) 0.2430(13) 0.136(8) Uani 1 1 d . . . H33A H -0.0603 0.5730 0.2512 0.163 Uiso 1 1 calc R . . H33B H -0.0901 0.4812 0.2396 0.163 Uiso 1 1 calc R . . C34 C 0.4268(11) 0.8952(12) -0.0422(12) 0.125(6) Uani 1 1 d . . . H34A H 0.4221 0.9530 -0.0310 0.150 Uiso 1 1 calc R . . H34B H 0.4078 0.8888 -0.1000 0.150 Uiso 1 1 calc R . . Cl7A Cl 0.4050(2) 0.4618(3) 0.5215(2) 0.0934(11) Uani 1 1 d . . . Cl7B Cl 0.2405(3) 0.5427(3) 0.4821(3) 0.1113(14) Uani 1 1 d . . . Cl8A Cl -0.0155(3) 0.5148(3) 0.1541(2) 0.1127(14) Uani 1 1 d . . . Cl8B Cl 0.0406(4) 0.4914(3) 0.3216(3) 0.1286(17) Uani 1 1 d . . . Cl9A Cl 0.3589(3) 0.8453(3) -0.0056(4) 0.143(2) Uani 1 1 d . . . Cl9B Cl 0.5331(3) 0.8691(3) -0.0099(5) 0.173(3) Uani 1 1 d . . . C1 C 0.4119(4) 0.4575(4) 0.1178(4) 0.0251(14) Uani 1 1 d . . . C2 C 0.4596(4) 0.4273(4) 0.0637(4) 0.0245(14) Uani 1 1 d . . . C3 C 0.4786(4) 0.5007(4) 0.0283(4) 0.0245(13) Uani 1 1 d . . . C4 C 0.4495(4) 0.5759(4) 0.0526(4) 0.0258(14) Uani 1 1 d . . . C5 C 0.4058(4) 0.5493(4) 0.1112(4) 0.0246(14) Uani 1 1 d . . . C6 C 0.4859(5) 0.3532(4) 0.0397(4) 0.0298(15) Uani 1 1 d . . . H6 H 0.4728 0.3044 0.0613 0.036 Uiso 1 1 calc R . . C7 C 0.4670(5) 0.6481(4) 0.0181(4) 0.0291(15) Uani 1 1 d . . . H7 H 0.4478 0.6978 0.0329 0.035 Uiso 1 1 calc R . . C8 C 0.3538(5) 0.3424(4) 0.1739(4) 0.0298(15) Uani 1 1 d . . . C9 C 0.2840(5) 0.3063(4) 0.1176(5) 0.0341(17) Uani 1 1 d . . . C10 C 0.2661(6) 0.2249(5) 0.1315(5) 0.045(2) Uani 1 1 d . . . H10 H 0.2191 0.1986 0.0963 0.054 Uiso 1 1 calc R . . C11 C 0.3178(6) 0.1825(5) 0.1976(5) 0.048(2) Uani 1 1 d . . . H11 H 0.3040 0.1288 0.2069 0.058 Uiso 1 1 calc R . . C12 C 0.3877(6) 0.2187(5) 0.2481(6) 0.047(2) Uani 1 1 d . . . H12 H 0.4220 0.1887 0.2909 0.057 Uiso 1 1 calc R . . C13 C 0.4101(5) 0.3004(5) 0.2381(5) 0.0342(16) Uani 1 1 d . . . C14 C 0.2292(6) 0.3473(5) 0.0417(5) 0.044(2) Uani 1 1 d . . . H14 H 0.2479 0.4045 0.0425 0.053 Uiso 1 1 calc R . . C15 C 0.2455(7) 0.3053(7) -0.0323(5) 0.060(3) Uani 1 1 d . . . H15A H 0.2216 0.2509 -0.0378 0.090 Uiso 1 1 calc R . . H15B H 0.3068 0.3022 -0.0255 0.090 Uiso 1 1 calc R . . H15C H 0.2183 0.3365 -0.0795 0.090 Uiso 1 1 calc R . . C16 C 0.1336(6) 0.3467(7) 0.0336(6) 0.061(3) Uani 1 1 d . . . H16A H 0.1137 0.2911 0.0321 0.091 Uiso 1 1 calc R . . H16B H 0.1030 0.3741 -0.0151 0.091 Uiso 1 1 calc R . . H16C H 0.1232 0.3746 0.0784 0.091 Uiso 1 1 calc R . . C17 C 0.4929(5) 0.3361(5) 0.2929(5) 0.0423(19) Uani 1 1 d . . . H17 H 0.4940 0.3948 0.2810 0.051 Uiso 1 1 calc R . . C18 C 0.5722(6) 0.2953(7) 0.2743(7) 0.065(3) Uani 1 1 d . . . H18A H 0.5729 0.2378 0.2863 0.098 Uiso 1 1 calc R . . H18B H 0.6247 0.3202 0.3066 0.098 Uiso 1 1 calc R . . H18C H 0.5680 0.3026 0.2187 0.098 Uiso 1 1 calc R . . C19 C 0.4998(7) 0.3270(7) 0.3813(6) 0.063(3) Uani 1 1 d . . . H19A H 0.4505 0.3524 0.3922 0.095 Uiso 1 1 calc R . . H19B H 0.5520 0.3529 0.4128 0.095 Uiso 1 1 calc R . . H19C H 0.5012 0.2698 0.3948 0.095 Uiso 1 1 calc R . . C20 C 0.3333(5) 0.6649(4) 0.1534(4) 0.0308(16) Uani 1 1 d . . . C21 C 0.2571(5) 0.6898(5) 0.0962(5) 0.0376(18) Uani 1 1 d . . . C22 C 0.2296(6) 0.7700(5) 0.1012(5) 0.049(2) Uani 1 1 d . . . H22 H 0.1788 0.7885 0.0646 0.059 Uiso 1 1 calc R . . C23 C 0.2771(6) 0.8225(5) 0.1600(6) 0.050(2) Uani 1 1 d . . . H23 H 0.2571 0.8755 0.1633 0.060 Uiso 1 1 calc R . . C24 C 0.3524(7) 0.7975(5) 0.2129(6) 0.051(2) Uani 1 1 d . . . H24 H 0.3832 0.8342 0.2514 0.062 Uiso 1 1 calc R . . C25 C 0.3854(6) 0.7175(5) 0.2113(5) 0.0393(18) Uani 1 1 d . . . C26 C 0.2040(6) 0.6372(6) 0.0274(5) 0.044(2) Uani 1 1 d . . . H26 H 0.2282 0.5816 0.0344 0.053 Uiso 1 1 calc R . . C27 C 0.1081(6) 0.6320(6) 0.0260(6) 0.060(3) Uani 1 1 d . . . H27A H 0.1041 0.6104 0.0761 0.090 Uiso 1 1 calc R . . H27B H 0.0775 0.5967 -0.0169 0.090 Uiso 1 1 calc R . . H27C H 0.0828 0.6858 0.0180 0.090 Uiso 1 1 calc R . . C28 C 0.2110(7) 0.6705(7) -0.0531(5) 0.059(3) Uani 1 1 d . . . H28A H 0.1887 0.7254 -0.0608 0.089 Uiso 1 1 calc R . . H28B H 0.1779 0.6363 -0.0959 0.089 Uiso 1 1 calc R . . H28C H 0.2707 0.6706 -0.0530 0.089 Uiso 1 1 calc R . . C29 C 0.4726(6) 0.6952(6) 0.2648(5) 0.048(2) Uani 1 1 d . . . H29 H 0.4805 0.6360 0.2598 0.058 Uiso 1 1 calc R . . C30 C 0.5439(7) 0.7392(7) 0.2377(7) 0.067(3) Uani 1 1 d . . . H30A H 0.5428 0.7207 0.1851 0.101 Uiso 1 1 calc R . . H30B H 0.5995 0.7273 0.2746 0.101 Uiso 1 1 calc R . . H30C H 0.5339 0.7973 0.2365 0.101 Uiso 1 1 calc R . . C31 C 0.4840(7) 0.7142(7) 0.3533(6) 0.068(3) Uani 1 1 d . . . H31A H 0.4855 0.7725 0.3611 0.102 Uiso 1 1 calc R . . H31B H 0.5374 0.6905 0.3854 0.102 Uiso 1 1 calc R . . H31C H 0.4362 0.6914 0.3689 0.102 Uiso 1 1 calc R . . B1 B 0.3295(5) 0.5050(5) 0.2026(4) 0.0270(16) Uani 1 1 d . . . B2 B 0.7092(6) 0.5207(7) 0.2235(7) 0.051(3) Uani 1 1 d . . . N1 N 0.3699(3) 0.4295(3) 0.1645(3) 0.0236(12) Uani 1 1 d . . . N2 N 0.3591(3) 0.5788(3) 0.1527(3) 0.0252(12) Uani 1 1 d . . . Cl1 Cl 0.21407(11) 0.49698(11) 0.17822(11) 0.0356(5) Uani 1 1 d . . . Cl2 Cl 0.38103(14) 0.51488(13) 0.30773(11) 0.0418(5) Uani 1 1 d . . . Cl3 Cl 0.59629(13) 0.51870(15) 0.23453(13) 0.0498(6) Uani 1 1 d . . . Cl4 Cl 0.70269(17) 0.50635(18) 0.11732(15) 0.0639(7) Uani 1 1 d . . . Cl5 Cl 0.75885(17) 0.6214(2) 0.2566(2) 0.0778(9) Uani 1 1 d . . . Cl6 Cl 0.77205(18) 0.4385(2) 0.2842(2) 0.0991(13) 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 C32 0.078(8) 0.108(10) 0.064(7) 0.019(7) 0.028(6) -0.003(7) C33 0.100(12) 0.149(15) 0.201(19) 0.099(14) 0.111(13) 0.063(11) C34 0.093(11) 0.146(15) 0.154(16) 0.046(13) 0.063(11) -0.002(11) Cl7A 0.081(2) 0.122(3) 0.075(2) -0.0046(19) 0.0188(17) 0.002(2) Cl7B 0.101(3) 0.103(3) 0.123(3) 0.048(2) 0.020(2) 0.020(2) Cl8A 0.076(2) 0.169(4) 0.087(2) 0.001(2) 0.0121(19) -0.036(2) Cl8B 0.121(4) 0.168(5) 0.098(3) -0.005(3) 0.033(3) 0.001(3) Cl9A 0.137(4) 0.088(3) 0.229(6) 0.068(3) 0.094(4) 0.041(3) Cl9B 0.115(4) 0.066(2) 0.357(10) 0.005(4) 0.097(5) -0.007(2) C1 0.023(3) 0.025(3) 0.029(3) -0.001(3) 0.010(3) 0.000(3) C2 0.027(3) 0.024(3) 0.027(3) -0.001(3) 0.016(3) 0.002(3) C3 0.028(3) 0.022(3) 0.025(3) 0.000(3) 0.012(3) -0.001(3) C4 0.028(3) 0.021(3) 0.033(4) -0.001(3) 0.015(3) 0.001(3) C5 0.026(3) 0.026(3) 0.025(3) 0.001(3) 0.012(3) 0.001(3) C6 0.035(4) 0.024(3) 0.036(4) 0.005(3) 0.019(3) 0.005(3) C7 0.032(4) 0.022(3) 0.037(4) 0.002(3) 0.017(3) 0.003(3) C8 0.039(4) 0.023(3) 0.035(4) 0.003(3) 0.022(3) 0.000(3) C9 0.044(4) 0.028(4) 0.038(4) -0.001(3) 0.023(3) -0.009(3) C10 0.057(5) 0.034(4) 0.051(5) -0.004(4) 0.028(4) -0.013(4) C11 0.073(6) 0.032(4) 0.050(5) 0.009(4) 0.035(5) -0.005(4) C12 0.058(6) 0.032(4) 0.058(5) 0.016(4) 0.025(5) 0.005(4) C13 0.036(4) 0.031(4) 0.041(4) 0.009(3) 0.019(3) 0.006(3) C14 0.051(5) 0.040(5) 0.037(4) 0.002(4) 0.005(4) -0.017(4) C15 0.077(7) 0.072(7) 0.032(4) -0.008(4) 0.019(4) -0.029(5) C16 0.054(6) 0.064(6) 0.056(6) -0.001(5) 0.003(5) -0.017(5) C17 0.041(4) 0.041(5) 0.043(4) 0.017(4) 0.010(4) 0.008(4) C18 0.046(6) 0.068(7) 0.084(7) 0.022(6) 0.022(5) 0.016(5) C19 0.069(7) 0.061(6) 0.051(5) 0.022(5) 0.004(5) 0.003(5) C20 0.037(4) 0.024(3) 0.038(4) -0.004(3) 0.023(3) 0.002(3) C21 0.041(4) 0.037(4) 0.042(4) 0.007(3) 0.023(4) 0.013(3) C22 0.058(6) 0.041(5) 0.054(5) 0.010(4) 0.027(4) 0.020(4) C23 0.065(6) 0.030(4) 0.066(6) -0.001(4) 0.034(5) 0.011(4) C24 0.073(7) 0.034(4) 0.058(6) -0.015(4) 0.036(5) -0.008(4) C25 0.049(5) 0.031(4) 0.048(5) -0.009(3) 0.030(4) -0.005(3) C26 0.046(5) 0.049(5) 0.036(4) 0.004(4) 0.011(4) 0.016(4) C27 0.043(5) 0.061(6) 0.067(6) 0.002(5) 0.002(5) 0.013(4) C28 0.056(6) 0.079(7) 0.046(5) 0.017(5) 0.018(4) 0.021(5) C29 0.042(5) 0.048(5) 0.054(5) -0.016(4) 0.013(4) -0.001(4) C30 0.050(6) 0.063(6) 0.093(8) -0.030(6) 0.027(6) -0.019(5) C31 0.072(7) 0.063(6) 0.062(6) -0.029(5) 0.010(5) -0.013(5) B1 0.028(4) 0.032(4) 0.022(4) 0.000(3) 0.009(3) 0.000(3) B2 0.029(5) 0.066(7) 0.055(6) 0.005(5) 0.006(4) 0.002(4) N1 0.022(3) 0.027(3) 0.024(3) 0.003(2) 0.010(2) 0.002(2) N2 0.022(3) 0.029(3) 0.024(3) -0.004(2) 0.007(2) 0.000(2) Cl1 0.0273(9) 0.0417(10) 0.0421(10) 0.0019(8) 0.0166(7) 0.0018(7) Cl2 0.0484(11) 0.0541(12) 0.0236(8) -0.0015(8) 0.0117(8) 0.0011(9) Cl3 0.0297(10) 0.0722(15) 0.0475(12) 0.0023(10) 0.0110(8) -0.0001(9) Cl4 0.0497(13) 0.091(2) 0.0555(14) -0.0106(13) 0.0225(11) -0.0042(12) Cl5 0.0469(14) 0.088(2) 0.100(2) -0.0349(17) 0.0239(14) -0.0190(13) Cl6 0.0448(15) 0.125(3) 0.131(3) 0.075(2) 0.0317(16) 0.0281(16) _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 C32 Cl7B 1.722(13) . ? C32 Cl7A 1.745(13) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 Cl8B 1.66(2) . ? C33 Cl8A 1.720(18) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 Cl9A 1.630(15) . ? C34 Cl9B 1.694(17) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C1 N1 1.281(8) . ? C1 C2 1.459(9) . ? C1 C5 1.503(9) . ? C2 C6 1.384(9) . ? C2 C3 1.420(9) . ? C3 C3 1.356(13) 3_665 ? C3 C4 1.420(9) . ? C4 C7 1.388(9) . ? C4 C5 1.461(9) . ? C5 N2 1.277(8) . ? C6 C7 1.423(10) 3_665 ? C6 H6 0.9300 . ? C7 C6 1.423(10) 3_665 ? C7 H7 0.9300 . ? C8 C9 1.392(11) . ? C8 C13 1.400(10) . ? C8 N1 1.461(9) . ? C9 C10 1.394(10) . ? C9 C14 1.517(11) . ? C10 C11 1.396(13) . ? C10 H10 0.9300 . ? C11 C12 1.348(13) . ? C11 H11 0.9300 . ? C12 C13 1.403(11) . ? C12 H12 0.9300 . ? C13 C17 1.515(12) . ? C14 C16 1.502(13) . ? C14 C15 1.548(12) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C19 1.521(12) . ? C17 C18 1.552(13) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C25 1.404(11) . ? C20 C21 1.399(11) . ? C20 N2 1.465(9) . ? C21 C22 1.392(11) . ? C21 C26 1.520(12) . ? C22 C23 1.385(13) . ? C22 H22 0.9300 . ? C23 C24 1.356(14) . ? C23 H23 0.9300 . ? C24 C25 1.412(12) . ? C24 H24 0.9300 . ? C25 C29 1.489(12) . ? C26 C27 1.537(13) . ? C26 C28 1.539(12) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C31 1.532(13) . ? C29 C30 1.536(13) . ? C29 H29 0.9800 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? B1 N1 1.620(9) . ? B1 N2 1.633(9) . ? B1 Cl1 1.786(8) . ? B1 Cl2 1.789(8) . ? B2 Cl6 1.824(11) . ? B2 Cl5 1.845(12) . ? B2 Cl4 1.838(12) . ? B2 Cl3 1.880(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl7B C32 Cl7A 111.0(7) . . ? Cl7B C32 H32A 109.4 . . ? Cl7A C32 H32A 109.4 . . ? Cl7B C32 H32B 109.4 . . ? Cl7A C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? Cl8B C33 Cl8A 113.0(8) . . ? Cl8B C33 H33A 109.0 . . ? Cl8A C33 H33A 109.0 . . ? Cl8B C33 H33B 109.0 . . ? Cl8A C33 H33B 109.0 . . ? H33A C33 H33B 107.8 . . ? Cl9A C34 Cl9B 118.0(11) . . ? Cl9A C34 H34A 107.8 . . ? Cl9B C34 H34A 107.8 . . ? Cl9A C34 H34B 107.8 . . ? Cl9B C34 H34B 107.8 . . ? H34A C34 H34B 107.1 . . ? N1 C1 C2 139.4(6) . . ? N1 C1 C5 111.6(6) . . ? C2 C1 C5 108.8(5) . . ? C6 C2 C3 118.8(6) . . ? C6 C2 C1 138.8(6) . . ? C3 C2 C1 102.3(5) . . ? C3 C3 C2 121.3(8) 3_665 . ? C3 C3 C4 120.7(8) 3_665 . ? C2 C3 C4 117.9(6) . . ? C7 C4 C3 118.6(6) . . ? C7 C4 C5 138.8(6) . . ? C3 C4 C5 102.6(5) . . ? N2 C5 C4 139.7(6) . . ? N2 C5 C1 111.7(6) . . ? C4 C5 C1 108.3(5) . . ? C2 C6 C7 119.8(6) . 3_665 ? C2 C6 H6 120.1 . . ? C7 C6 H6 120.1 3_665 . ? C4 C7 C6 120.7(6) . 3_665 ? C4 C7 H7 119.7 . . ? C6 C7 H7 119.7 3_665 . ? C9 C8 C13 124.1(7) . . ? C9 C8 N1 117.7(6) . . ? C13 C8 N1 118.1(6) . . ? C8 C9 C10 116.5(7) . . ? C8 C9 C14 125.3(6) . . ? C10 C9 C14 118.2(7) . . ? C11 C10 C9 120.7(8) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C12 C11 C10 120.6(7) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 122.0(8) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C12 C13 C8 115.7(8) . . ? C12 C13 C17 119.9(7) . . ? C8 C13 C17 124.4(7) . . ? C16 C14 C9 113.8(7) . . ? C16 C14 C15 109.4(7) . . ? C9 C14 C15 109.6(8) . . ? C16 C14 H14 108.0 . . ? C9 C14 H14 108.0 . . ? C15 C14 H14 108.0 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 C19 113.4(7) . . ? C13 C17 C18 109.2(8) . . ? C19 C17 C18 110.1(8) . . ? C13 C17 H17 108.0 . . ? C19 C17 H17 108.0 . . ? C18 C17 H17 108.0 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 123.7(7) . . ? C25 C20 N2 118.7(7) . . ? C21 C20 N2 117.6(6) . . ? C22 C21 C20 117.2(8) . . ? C22 C21 C26 117.5(8) . . ? C20 C21 C26 125.2(7) . . ? C23 C22 C21 120.7(9) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C24 C23 C22 120.8(8) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 122.1(9) . . ? C23 C24 H24 119.0 . . ? C25 C24 H24 119.0 . . ? C20 C25 C24 115.4(8) . . ? C20 C25 C29 124.1(7) . . ? C24 C25 C29 120.4(8) . . ? C21 C26 C27 112.2(7) . . ? C21 C26 C28 110.4(8) . . ? C27 C26 C28 109.9(7) . . ? C21 C26 H26 108.1 . . ? C27 C26 H26 108.1 . . ? C28 C26 H26 108.1 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 C31 113.5(8) . . ? C25 C29 C30 110.2(8) . . ? C31 C29 C30 109.3(8) . . ? C25 C29 H29 107.9 . . ? C31 C29 H29 107.9 . . ? C30 C29 H29 107.9 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N1 B1 N2 97.5(5) . . ? N1 B1 Cl1 111.0(5) . . ? N2 B1 Cl1 111.6(5) . . ? N1 B1 Cl2 111.5(5) . . ? N2 B1 Cl2 111.0(5) . . ? Cl1 B1 Cl2 113.2(4) . . ? Cl6 B2 Cl5 110.8(6) . . ? Cl6 B2 Cl4 110.7(6) . . ? Cl5 B2 Cl4 108.8(6) . . ? Cl6 B2 Cl3 108.6(6) . . ? Cl5 B2 Cl3 109.1(6) . . ? Cl4 B2 Cl3 108.8(5) . . ? C1 N1 C8 124.1(6) . . ? C1 N1 B1 109.6(5) . . ? C8 N1 B1 126.0(5) . . ? C5 N2 C20 125.5(6) . . ? C5 N2 B1 109.3(5) . . ? C20 N2 B1 125.2(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 N1 C1 C2 C6 -4.0(16) . . . . ? C5 C1 C2 C6 -178.3(8) . . . . ? N1 C1 C2 C3 174.1(9) . . . . ? C5 C1 C2 C3 -0.2(7) . . . . ? C6 C2 C3 C3 0.2(12) . . . 3_665 ? C1 C2 C3 C3 -178.3(8) . . . 3_665 ? C6 C2 C3 C4 178.8(7) . . . . ? C1 C2 C3 C4 0.2(8) . . . . ? C3 C3 C4 C7 -1.0(12) 3_665 . . . ? C2 C3 C4 C7 -179.5(6) . . . . ? C3 C3 C4 C5 178.5(8) 3_665 . . . ? C2 C3 C4 C5 -0.1(8) . . . . ? C7 C4 C5 N2 6.5(16) . . . . ? C3 C4 C5 N2 -172.7(9) . . . . ? C7 C4 C5 C1 179.1(8) . . . . ? C3 C4 C5 C1 -0.1(7) . . . . ? N1 C1 C5 N2 -0.9(8) . . . . ? C2 C1 C5 N2 175.1(6) . . . . ? N1 C1 C5 C4 -175.8(6) . . . . ? C2 C1 C5 C4 0.2(7) . . . . ? C3 C2 C6 C7 1.5(11) . . . 3_665 ? C1 C2 C6 C7 179.4(8) . . . 3_665 ? C3 C4 C7 C6 -0.8(11) . . . 3_665 ? C5 C4 C7 C6 -180.0(8) . . . 3_665 ? C13 C8 C9 C10 5.8(11) . . . . ? N1 C8 C9 C10 -175.2(6) . . . . ? C13 C8 C9 C14 -171.6(7) . . . . ? N1 C8 C9 C14 7.4(11) . . . . ? C8 C9 C10 C11 -1.7(11) . . . . ? C14 C9 C10 C11 175.9(8) . . . . ? C9 C10 C11 C12 -1.9(13) . . . . ? C10 C11 C12 C13 1.7(13) . . . . ? C11 C12 C13 C8 2.0(12) . . . . ? C11 C12 C13 C17 -175.5(8) . . . . ? C9 C8 C13 C12 -5.9(11) . . . . ? N1 C8 C13 C12 175.1(6) . . . . ? C9 C8 C13 C17 171.5(7) . . . . ? N1 C8 C13 C17 -7.6(10) . . . . ? C8 C9 C14 C16 -125.4(9) . . . . ? C10 C9 C14 C16 57.2(10) . . . . ? C8 C9 C14 C15 111.8(8) . . . . ? C10 C9 C14 C15 -65.6(9) . . . . ? C12 C13 C17 C19 -53.8(10) . . . . ? C8 C13 C17 C19 128.9(8) . . . . ? C12 C13 C17 C18 69.3(9) . . . . ? C8 C13 C17 C18 -107.9(9) . . . . ? C25 C20 C21 C22 -4.3(11) . . . . ? N2 C20 C21 C22 175.3(7) . . . . ? C25 C20 C21 C26 173.4(7) . . . . ? N2 C20 C21 C26 -7.1(11) . . . . ? C20 C21 C22 C23 0.9(12) . . . . ? C26 C21 C22 C23 -176.9(8) . . . . ? C21 C22 C23 C24 1.5(14) . . . . ? C22 C23 C24 C25 -0.7(14) . . . . ? C21 C20 C25 C24 5.0(11) . . . . ? N2 C20 C25 C24 -174.5(6) . . . . ? C21 C20 C25 C29 -170.9(8) . . . . ? N2 C20 C25 C29 9.6(11) . . . . ? C23 C24 C25 C20 -2.4(12) . . . . ? C23 C24 C25 C29 173.6(8) . . . . ? C22 C21 C26 C27 -56.2(10) . . . . ? C20 C21 C26 C27 126.2(8) . . . . ? C22 C21 C26 C28 66.7(10) . . . . ? C20 C21 C26 C28 -110.9(9) . . . . ? C20 C25 C29 C31 -130.9(9) . . . . ? C24 C25 C29 C31 53.4(11) . . . . ? C20 C25 C29 C30 106.1(9) . . . . ? C24 C25 C29 C30 -69.5(10) . . . . ? C2 C1 N1 C8 -3.1(13) . . . . ? C5 C1 N1 C8 171.0(6) . . . . ? C2 C1 N1 B1 -177.0(8) . . . . ? C5 C1 N1 B1 -2.8(7) . . . . ? C9 C8 N1 C1 -82.8(9) . . . . ? C13 C8 N1 C1 96.3(8) . . . . ? C9 C8 N1 B1 90.0(8) . . . . ? C13 C8 N1 B1 -90.9(8) . . . . ? N2 B1 N1 C1 4.6(7) . . . . ? Cl1 B1 N1 C1 121.2(5) . . . . ? Cl2 B1 N1 C1 -111.6(6) . . . . ? N2 B1 N1 C8 -169.1(6) . . . . ? Cl1 B1 N1 C8 -52.4(8) . . . . ? Cl2 B1 N1 C8 74.7(7) . . . . ? C4 C5 N2 C20 -1.4(13) . . . . ? C1 C5 N2 C20 -173.9(6) . . . . ? C4 C5 N2 B1 176.6(8) . . . . ? C1 C5 N2 B1 4.1(7) . . . . ? C25 C20 N2 C5 -92.6(8) . . . . ? C21 C20 N2 C5 87.9(9) . . . . ? C25 C20 N2 B1 89.7(8) . . . . ? C21 C20 N2 B1 -89.8(8) . . . . ? N1 B1 N2 C5 -5.2(7) . . . . ? Cl1 B1 N2 C5 -121.3(6) . . . . ? Cl2 B1 N2 C5 111.4(6) . . . . ? N1 B1 N2 C20 172.9(6) . . . . ? Cl1 B1 N2 C20 56.7(8) . . . . ? Cl2 B1 N2 C20 -70.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.20 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.187 _refine_diff_density_min -1.165 _refine_diff_density_rms 0.137 # Attachment 'Compound 4.cif' data_ccdkvkv016a _database_code_depnum_ccdc_archive 'CCDC 670788' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _publ_section_synopsis ; ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Sluis, P. v.d. & Spek, A. L. (1990). SQUEEZE. Acta Cryst. A46, 194-201. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H48 N4, C H2 Cl2' _chemical_formula_sum 'C51 H50 Cl2 N4' _chemical_formula_weight 789.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M p21/c _symmetry_space_group_name_Hall -p2ybc 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 13.568(3) _cell_length_b 24.864(5) _cell_length_c 13.852(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.16(3) _cell_angle_gamma 90.00 _cell_volume 4357.6(15) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max .20 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1672 _exptl_absorpt_coefficient_mu 0.188 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28050 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 27.46 _reflns_number_total 9946 _reflns_number_gt 6382 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.1056P)^2^+0.6509P] 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 9946 _refine_ls_number_parameters 526 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0970 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1841 _refine_ls_wR_factor_gt 0.1519 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.011 _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 C51 C 0.14703(19) 0.86818(10) 0.9549(2) 0.0510(6) Uani 1 1 d . . . H51A H 0.1069 0.8359 0.9552 0.061 Uiso 1 1 calc R . . H52B H 0.1014 0.8923 0.9028 0.061 Uiso 1 1 calc R . . Cl1 Cl 0.25591(6) 0.85078(3) 0.92111(7) 0.0712(2) Uani 1 1 d . . . Cl2 Cl 0.18354(6) 0.89939(3) 1.07679(6) 0.0700(2) Uani 1 1 d . . . C1 C -0.03729(14) 0.96550(7) 0.73563(15) 0.0281(4) Uani 1 1 d . . . C2 C -0.05499(14) 0.90991(8) 0.69236(14) 0.0274(4) Uani 1 1 d . . . C3 C -0.13354(14) 0.87096(8) 0.66786(15) 0.0299(4) Uani 1 1 d . . . H3 H -0.1941 0.8772 0.6828 0.036 Uiso 1 1 calc R . . C4 C -0.12307(14) 0.82185(7) 0.62039(15) 0.0288(4) Uani 1 1 d . . . H4 H -0.1771 0.7965 0.6043 0.035 Uiso 1 1 calc R . . C5 C -0.03338(14) 0.81092(7) 0.59760(14) 0.0269(4) Uani 1 1 d . . . C6 C 0.00503(14) 0.76817(7) 0.54414(15) 0.0277(4) Uani 1 1 d . . . C7 C 0.11531(14) 0.78607(8) 0.54837(15) 0.0284(4) Uani 1 1 d . . . C8 C 0.13530(14) 0.84010(8) 0.59788(15) 0.0286(4) Uani 1 1 d . . . C9 C 0.21233(15) 0.87953(8) 0.61883(16) 0.0314(4) Uani 1 1 d . . . H9 H 0.2717 0.8737 0.6016 0.038 Uiso 1 1 calc R . . C10 C 0.20160(14) 0.92879(8) 0.66642(16) 0.0313(4) Uani 1 1 d . . . H10 H 0.2545 0.9547 0.6807 0.038 Uiso 1 1 calc R . . C11 C 0.04622(14) 0.85059(7) 0.62441(14) 0.0267(4) Uani 1 1 d . . . C12 C 0.03569(14) 0.89819(7) 0.66947(14) 0.0263(4) Uani 1 1 d . . . C13 C 0.11342(14) 0.93867(7) 0.69178(15) 0.0278(4) Uani 1 1 d . . . C14 C 0.07294(14) 0.98304(7) 0.73879(15) 0.0277(4) Uani 1 1 d . . . C15 C -0.19879(15) 0.97967(8) 0.75339(16) 0.0327(4) Uani 1 1 d . . . C16 C -0.28506(17) 0.99674(9) 0.66818(18) 0.0394(5) Uani 1 1 d . . . C17 C -0.38546(17) 0.98061(10) 0.66203(19) 0.0472(6) Uani 1 1 d . . . H17 H -0.4439 0.9918 0.6059 0.057 Uiso 1 1 calc R . . C18 C -0.40097(17) 0.94844(10) 0.7370(2) 0.0470(6) Uani 1 1 d . . . C19 C -0.31336(17) 0.93234(9) 0.82044(19) 0.0423(5) Uani 1 1 d . . . H19 H -0.3231 0.9104 0.8706 0.051 Uiso 1 1 calc R . . C20 C -0.21112(16) 0.94794(8) 0.83183(17) 0.0360(5) Uani 1 1 d . . . C21 C -0.2685(2) 1.03028(12) 0.5847(2) 0.0612(7) Uani 1 1 d . . . H21A H -0.2199 1.0589 0.6159 0.092 Uiso 1 1 calc R . . H21B H -0.3349 1.0452 0.5409 0.092 Uiso 1 1 calc R . . H21C H -0.2402 1.0081 0.5441 0.092 Uiso 1 1 calc R . . C22 C -0.51117(19) 0.93160(12) 0.7282(3) 0.0671(8) Uani 1 1 d . . . H22A H -0.5136 0.8932 0.7348 0.101 Uiso 1 1 calc R . . H22B H -0.5610 0.9425 0.6621 0.101 Uiso 1 1 calc R . . H22C H -0.5288 0.9484 0.7823 0.101 Uiso 1 1 calc R . . C23 C -0.11814(18) 0.93057(10) 0.92403(19) 0.0507(6) Uani 1 1 d . . . H23A H -0.1414 0.9213 0.9796 0.076 Uiso 1 1 calc R . . H23B H -0.0679 0.9594 0.9454 0.076 Uiso 1 1 calc R . . H23C H -0.0856 0.8998 0.9060 0.076 Uiso 1 1 calc R . . C24 C -0.14342(15) 0.71363(7) 0.49311(15) 0.0287(4) Uani 1 1 d . . . C25 C -0.22886(16) 0.73139(8) 0.40715(15) 0.0333(4) Uani 1 1 d . . . C26 C -0.33067(16) 0.71959(9) 0.40377(16) 0.0373(5) Uani 1 1 d . . . H26 H -0.3882 0.7318 0.3479 0.045 Uiso 1 1 calc R . . C27 C -0.34926(15) 0.69025(8) 0.48085(16) 0.0342(5) Uani 1 1 d . . . C28 C -0.26236(15) 0.67240(8) 0.56330(15) 0.0317(4) Uani 1 1 d . . . H28 H -0.2736 0.6522 0.6149 0.038 Uiso 1 1 calc R . . C29 C -0.15898(15) 0.68340(7) 0.57201(15) 0.0297(4) Uani 1 1 d . . . C30 C -0.2109(2) 0.76239(10) 0.32110(18) 0.0493(6) Uani 1 1 d . . . H30A H -0.1846 0.7976 0.3455 0.074 Uiso 1 1 calc R . . H30B H -0.2763 0.7655 0.2634 0.074 Uiso 1 1 calc R . . H30C H -0.1602 0.7437 0.2998 0.074 Uiso 1 1 calc R . . C31 C -0.46084(17) 0.67748(10) 0.4741(2) 0.0493(6) Uani 1 1 d . . . H31A H -0.5101 0.6991 0.4210 0.074 Uiso 1 1 calc R . . H31B H -0.4676 0.6851 0.5394 0.074 Uiso 1 1 calc R . . H31C H -0.4754 0.6401 0.4577 0.074 Uiso 1 1 calc R . . C32 C -0.06695(16) 0.66435(9) 0.66245(17) 0.0409(5) Uani 1 1 d . . . H32A H -0.0126 0.6516 0.6390 0.061 Uiso 1 1 calc R . . H32B H -0.0890 0.6356 0.6964 0.061 Uiso 1 1 calc R . . H32C H -0.0400 0.6935 0.7101 0.061 Uiso 1 1 calc R . . C33 C 0.27155(14) 0.77835(8) 0.51812(15) 0.0298(4) Uani 1 1 d . . . C34 C 0.27917(15) 0.80565(8) 0.43303(15) 0.0334(5) Uani 1 1 d . . . C35 C 0.37735(16) 0.82541(9) 0.44037(16) 0.0381(5) Uani 1 1 d . . . H35 H 0.3831 0.8443 0.3847 0.046 Uiso 1 1 calc R . . C36 C 0.46692(16) 0.81801(9) 0.52785(17) 0.0391(5) Uani 1 1 d . . . C37 C 0.45631(16) 0.78970(9) 0.60987(16) 0.0377(5) Uani 1 1 d . . . H37 H 0.5161 0.7840 0.6687 0.045 Uiso 1 1 calc R . . C38 C 0.36018(16) 0.76950(8) 0.60765(15) 0.0329(4) Uani 1 1 d . . . C39 C 0.18215(17) 0.81397(11) 0.33820(17) 0.0484(6) Uani 1 1 d . . . H39A H 0.1325 0.8358 0.3554 0.073 Uiso 1 1 calc R . . H39B H 0.1506 0.7798 0.3127 0.073 Uiso 1 1 calc R . . H39C H 0.2013 0.8316 0.2859 0.073 Uiso 1 1 calc R . . C40 C 0.57310(18) 0.83949(12) 0.5341(2) 0.0565(7) Uani 1 1 d . . . H40A H 0.6204 0.8398 0.6050 0.085 Uiso 1 1 calc R . . H40B H 0.5649 0.8754 0.5070 0.085 Uiso 1 1 calc R . . H40C H 0.6015 0.8169 0.4942 0.085 Uiso 1 1 calc R . . C41 C 0.35028(19) 0.74005(10) 0.69874(18) 0.0456(6) Uani 1 1 d . . . H41A H 0.4195 0.7326 0.7483 0.068 Uiso 1 1 calc R . . H41B H 0.3131 0.7069 0.6756 0.068 Uiso 1 1 calc R . . H41C H 0.3120 0.7619 0.7303 0.068 Uiso 1 1 calc R . . C42 C 0.21280(15) 1.04300(7) 0.77362(15) 0.0291(4) Uani 1 1 d . . . C43 C 0.21529(16) 1.07100(8) 0.68714(16) 0.0363(5) Uani 1 1 d . . . C44 C 0.31319(18) 1.08928(9) 0.68857(19) 0.0454(6) Uani 1 1 d . . . H44 H 0.3162 1.1080 0.6316 0.054 Uiso 1 1 calc R . . C45 C 0.40609(17) 1.08044(9) 0.7722(2) 0.0457(6) Uani 1 1 d . . . C46 C 0.39987(16) 1.05231(9) 0.85576(18) 0.0409(5) Uani 1 1 d . . . H46 H 0.4616 1.0459 0.9122 0.049 Uiso 1 1 calc R . . C47 C 0.30464(16) 1.03326(8) 0.85852(16) 0.0329(4) Uani 1 1 d . . . C48 C 0.11568(19) 1.08044(11) 0.59557(18) 0.0513(6) Uani 1 1 d . . . H48A H 0.1301 1.1044 0.5479 0.077 Uiso 1 1 calc R . . H48B H 0.0633 1.0962 0.6184 0.077 Uiso 1 1 calc R . . H48C H 0.0900 1.0468 0.5618 0.077 Uiso 1 1 calc R . . C49 C 0.5113(2) 1.10129(12) 0.7732(3) 0.0724(9) Uani 1 1 d . . . H49A H 0.5538 1.1124 0.8421 0.109 Uiso 1 1 calc R . . H49B H 0.4997 1.1314 0.7270 0.109 Uiso 1 1 calc R . . H49C H 0.5472 1.0733 0.7511 0.109 Uiso 1 1 calc R . . C50 C 0.3014(2) 1.00160(10) 0.94975(18) 0.0492(6) Uani 1 1 d . . . H50A H 0.2984 0.9639 0.9341 0.074 Uiso 1 1 calc R . . H50B H 0.2399 1.0117 0.9644 0.074 Uiso 1 1 calc R . . H50C H 0.3637 1.0090 1.0090 0.074 Uiso 1 1 calc R . . N1 N -0.09584(13) 0.99771(6) 0.76194(14) 0.0336(4) Uani 1 1 d . . . N2 N -0.03805(12) 0.72544(6) 0.49786(13) 0.0313(4) Uani 1 1 d . . . N3 N 0.17091(12) 0.75723(6) 0.51169(13) 0.0313(4) Uani 1 1 d . . . N4 N 0.11258(12) 1.02790(6) 0.77678(13) 0.0314(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C51 0.0412(13) 0.0482(14) 0.0667(16) 0.0165(12) 0.0229(12) 0.0087(10) Cl1 0.0689(5) 0.0533(4) 0.1137(6) 0.0226(4) 0.0599(5) 0.0126(3) Cl2 0.0650(5) 0.0820(5) 0.0660(5) 0.0076(4) 0.0271(4) -0.0031(4) C1 0.0226(10) 0.0294(10) 0.0362(10) -0.0005(8) 0.0154(8) -0.0013(7) C2 0.0209(9) 0.0316(10) 0.0332(10) -0.0012(8) 0.0141(8) -0.0015(7) C3 0.0185(9) 0.0363(11) 0.0391(11) -0.0025(8) 0.0153(8) -0.0026(8) C4 0.0197(9) 0.0301(10) 0.0379(11) -0.0025(8) 0.0119(8) -0.0057(7) C5 0.0201(9) 0.0291(10) 0.0330(10) -0.0002(8) 0.0115(8) -0.0015(7) C6 0.0211(9) 0.0299(10) 0.0346(10) -0.0017(8) 0.0132(8) -0.0024(7) C7 0.0221(10) 0.0304(10) 0.0357(10) -0.0021(8) 0.0142(8) -0.0014(7) C8 0.0199(9) 0.0331(10) 0.0356(10) -0.0024(8) 0.0135(8) -0.0003(7) C9 0.0195(9) 0.0363(11) 0.0433(12) -0.0044(9) 0.0172(9) -0.0026(8) C10 0.0202(9) 0.0310(10) 0.0450(12) -0.0055(9) 0.0148(9) -0.0053(8) C11 0.0188(9) 0.0291(10) 0.0341(10) -0.0024(8) 0.0119(8) -0.0029(7) C12 0.0189(9) 0.0291(10) 0.0335(10) 0.0003(8) 0.0125(8) -0.0014(7) C13 0.0217(9) 0.0285(10) 0.0346(10) -0.0023(8) 0.0120(8) -0.0034(7) C14 0.0227(9) 0.0302(10) 0.0331(10) 0.0000(8) 0.0134(8) -0.0018(8) C15 0.0252(10) 0.0293(10) 0.0492(12) -0.0065(9) 0.0202(9) -0.0007(8) C16 0.0322(11) 0.0386(11) 0.0500(13) -0.0002(10) 0.0181(10) 0.0018(9) C17 0.0286(12) 0.0537(14) 0.0569(15) -0.0033(11) 0.0126(11) 0.0029(10) C18 0.0285(12) 0.0528(14) 0.0676(16) -0.0170(12) 0.0270(12) -0.0081(10) C19 0.0376(12) 0.0423(13) 0.0579(14) -0.0064(10) 0.0306(11) -0.0057(10) C20 0.0290(11) 0.0348(11) 0.0512(13) -0.0033(9) 0.0228(10) 0.0008(8) C21 0.0517(16) 0.0657(17) 0.0642(17) 0.0176(14) 0.0183(13) 0.0027(13) C22 0.0310(13) 0.082(2) 0.096(2) -0.0242(17) 0.0320(14) -0.0161(13) C23 0.0388(13) 0.0597(15) 0.0578(15) 0.0141(12) 0.0224(12) 0.0029(11) C24 0.0235(10) 0.0284(10) 0.0362(11) -0.0065(8) 0.0133(8) -0.0045(7) C25 0.0316(11) 0.0358(11) 0.0331(11) -0.0024(8) 0.0122(9) -0.0048(8) C26 0.0250(11) 0.0429(12) 0.0383(11) 0.0000(9) 0.0047(9) -0.0001(9) C27 0.0228(10) 0.0371(11) 0.0444(12) -0.0049(9) 0.0141(9) -0.0045(8) C28 0.0299(11) 0.0318(10) 0.0373(11) -0.0012(8) 0.0169(9) -0.0050(8) C29 0.0257(10) 0.0282(10) 0.0347(10) -0.0042(8) 0.0103(8) -0.0036(8) C30 0.0459(14) 0.0606(16) 0.0432(13) 0.0102(11) 0.0182(11) -0.0054(11) C31 0.0256(11) 0.0590(15) 0.0655(15) 0.0000(12) 0.0191(11) -0.0053(10) C32 0.0289(11) 0.0454(12) 0.0441(12) 0.0065(10) 0.0081(9) -0.0032(9) C33 0.0212(10) 0.0323(10) 0.0392(11) -0.0081(8) 0.0150(9) 0.0000(8) C34 0.0229(10) 0.0439(12) 0.0349(11) -0.0044(9) 0.0124(8) -0.0002(8) C35 0.0319(11) 0.0498(13) 0.0388(12) -0.0039(9) 0.0202(10) -0.0046(9) C36 0.0225(10) 0.0516(13) 0.0469(12) -0.0128(10) 0.0168(9) -0.0050(9) C37 0.0221(10) 0.0474(12) 0.0409(12) -0.0065(10) 0.0083(9) 0.0021(9) C38 0.0256(10) 0.0354(11) 0.0382(11) -0.0053(9) 0.0121(9) 0.0014(8) C39 0.0322(12) 0.0716(17) 0.0399(12) 0.0037(11) 0.0111(10) -0.0015(11) C40 0.0271(12) 0.0788(18) 0.0678(17) -0.0107(14) 0.0224(12) -0.0137(12) C41 0.0413(13) 0.0475(13) 0.0467(13) 0.0067(10) 0.0142(11) 0.0016(10) C42 0.0262(10) 0.0247(9) 0.0405(11) -0.0064(8) 0.0168(9) -0.0049(7) C43 0.0324(11) 0.0344(11) 0.0429(12) -0.0009(9) 0.0146(10) -0.0051(8) C44 0.0420(13) 0.0477(13) 0.0536(14) 0.0044(11) 0.0259(12) -0.0110(10) C45 0.0307(12) 0.0461(13) 0.0658(16) -0.0081(11) 0.0238(11) -0.0112(10) C46 0.0256(11) 0.0384(12) 0.0539(14) -0.0069(10) 0.0084(10) -0.0004(9) C47 0.0302(11) 0.0289(10) 0.0401(11) -0.0060(8) 0.0133(9) -0.0007(8) C48 0.0451(14) 0.0614(15) 0.0456(14) 0.0089(11) 0.0141(11) -0.0057(12) C49 0.0404(15) 0.080(2) 0.106(2) -0.0052(17) 0.0368(16) -0.0207(14) C50 0.0493(15) 0.0530(14) 0.0453(13) 0.0057(11) 0.0170(11) 0.0038(11) N1 0.0271(9) 0.0323(9) 0.0477(10) -0.0033(7) 0.0210(8) -0.0018(7) N2 0.0235(8) 0.0325(9) 0.0411(9) -0.0029(7) 0.0156(7) -0.0044(7) N3 0.0218(8) 0.0352(9) 0.0402(9) -0.0052(7) 0.0151(7) -0.0029(7) N4 0.0249(8) 0.0310(9) 0.0423(10) -0.0033(7) 0.0171(7) -0.0051(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C51 Cl1 1.757(2) . ? C51 Cl2 1.759(3) . ? C51 H51A 0.9700 . ? C51 H52B 0.9700 . ? C1 N1 1.271(2) . ? C1 C2 1.491(3) . ? C1 C14 1.543(3) . ? C2 C3 1.389(3) . ? C2 C12 1.407(2) . ? C3 C4 1.418(3) . ? C3 H3 0.9300 . ? C4 C5 1.390(3) . ? C4 H4 0.9300 . ? C5 C11 1.410(3) . ? C5 C6 1.493(3) . ? C6 N2 1.269(2) . ? C6 C7 1.542(2) . ? C7 N3 1.272(2) . ? C7 C8 1.488(3) . ? C8 C9 1.385(3) . ? C8 C11 1.409(2) . ? C9 C10 1.423(3) . ? C9 H9 0.9300 . ? C10 C13 1.385(3) . ? C10 H10 0.9300 . ? C11 C12 1.369(3) . ? C12 C13 1.409(3) . ? C13 C14 1.484(3) . ? C14 N4 1.267(2) . ? C15 C16 1.395(3) . ? C15 C20 1.401(3) . ? C15 N1 1.431(2) . ? C16 C17 1.393(3) . ? C16 C21 1.507(3) . ? C17 C18 1.386(3) . ? C17 H17 0.9300 . ? C18 C19 1.384(4) . ? C18 C22 1.515(3) . ? C19 C20 1.393(3) . ? C19 H19 0.9300 . ? C20 C23 1.499(3) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.400(3) . ? C24 C29 1.404(3) . ? C24 N2 1.437(2) . ? C25 C26 1.396(3) . ? C25 C30 1.511(3) . ? C26 C27 1.389(3) . ? C26 H26 0.9300 . ? C27 C28 1.385(3) . ? C27 C31 1.516(3) . ? C28 C29 1.391(3) . ? C28 H28 0.9300 . ? C29 C32 1.491(3) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.396(3) . ? C33 C38 1.398(3) . ? C33 N3 1.435(2) . ? C34 C35 1.389(3) . ? C34 C39 1.501(3) . ? C35 C36 1.384(3) . ? C35 H35 0.9300 . ? C36 C37 1.387(3) . ? C36 C40 1.509(3) . ? C37 C38 1.388(3) . ? C37 H37 0.9300 . ? C38 C41 1.506(3) . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C42 C47 1.392(3) . ? C42 C43 1.396(3) . ? C42 N4 1.427(2) . ? C43 C44 1.397(3) . ? C43 C48 1.501(3) . ? C44 C45 1.387(3) . ? C44 H44 0.9300 . ? C45 C46 1.381(3) . ? C45 C49 1.514(3) . ? C46 C47 1.390(3) . ? C46 H46 0.9300 . ? C47 C50 1.503(3) . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 0.9600 . ? 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 Cl1 C51 Cl2 113.07(14) . . ? Cl1 C51 H51A 109.0 . . ? Cl2 C51 H51A 109.0 . . ? Cl1 C51 H52B 109.0 . . ? Cl2 C51 H52B 109.0 . . ? H51A C51 H52B 107.8 . . ? N1 C1 C2 132.29(17) . . ? N1 C1 C14 120.91(17) . . ? C2 C1 C14 106.68(15) . . ? C3 C2 C12 117.18(17) . . ? C3 C2 C1 137.98(17) . . ? C12 C2 C1 104.80(15) . . ? C2 C3 C4 121.16(17) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 121.07(16) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C11 116.98(17) . . ? C4 C5 C6 137.99(17) . . ? C11 C5 C6 104.91(15) . . ? N2 C6 C5 131.83(17) . . ? N2 C6 C7 121.64(16) . . ? C5 C6 C7 106.47(15) . . ? N3 C7 C8 131.10(17) . . ? N3 C7 C6 121.96(17) . . ? C8 C7 C6 106.92(15) . . ? C9 C8 C11 117.89(17) . . ? C9 C8 C7 137.20(17) . . ? C11 C8 C7 104.87(15) . . ? C8 C9 C10 120.71(17) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C13 C10 C9 120.81(17) . . ? C13 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C12 C11 C8 121.29(17) . . ? C12 C11 C5 121.92(17) . . ? C8 C11 C5 116.72(17) . . ? C11 C12 C2 121.68(17) . . ? C11 C12 C13 121.63(17) . . ? C2 C12 C13 116.65(17) . . ? C10 C13 C12 117.67(17) . . ? C10 C13 C14 137.20(17) . . ? C12 C13 C14 105.14(15) . . ? N4 C14 C13 131.91(17) . . ? N4 C14 C1 121.47(16) . . ? C13 C14 C1 106.62(15) . . ? C16 C15 C20 121.93(18) . . ? C16 C15 N1 118.08(19) . . ? C20 C15 N1 119.92(19) . . ? C17 C16 C15 117.9(2) . . ? C17 C16 C21 121.7(2) . . ? C15 C16 C21 120.4(2) . . ? C18 C17 C16 122.0(2) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C19 C18 C17 118.4(2) . . ? C19 C18 C22 120.8(2) . . ? C17 C18 C22 120.8(2) . . ? C18 C19 C20 122.3(2) . . ? C18 C19 H19 118.9 . . ? C20 C19 H19 118.9 . . ? C19 C20 C15 117.5(2) . . ? C19 C20 C23 120.9(2) . . ? C15 C20 C23 121.59(18) . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 H22A 109.5 . . ? C18 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C18 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C29 121.33(17) . . ? C25 C24 N2 118.61(17) . . ? C29 C24 N2 120.02(17) . . ? C26 C25 C24 117.88(18) . . ? C26 C25 C30 121.35(19) . . ? C24 C25 C30 120.77(19) . . ? C27 C26 C25 122.44(19) . . ? C27 C26 H26 118.8 . . ? C25 C26 H26 118.8 . . ? C28 C27 C26 117.73(18) . . ? C28 C27 C31 121.14(19) . . ? C26 C27 C31 121.13(19) . . ? C27 C28 C29 122.68(18) . . ? C27 C28 H28 118.7 . . ? C29 C28 H28 118.7 . . ? C28 C29 C24 117.92(18) . . ? C28 C29 C32 121.51(18) . . ? C24 C29 C32 120.57(17) . . ? C25 C30 H30A 109.5 . . ? C25 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C25 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C27 C31 H31A 109.5 . . ? C27 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C27 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 C38 121.54(18) . . ? C34 C33 N3 118.97(17) . . ? C38 C33 N3 119.45(18) . . ? C35 C34 C33 118.15(18) . . ? C35 C34 C39 122.03(19) . . ? C33 C34 C39 119.81(18) . . ? C36 C35 C34 122.2(2) . . ? C36 C35 H35 118.9 . . ? C34 C35 H35 118.9 . . ? C35 C36 C37 117.81(18) . . ? C35 C36 C40 121.4(2) . . ? C37 C36 C40 120.8(2) . . ? C36 C37 C38 122.69(19) . . ? C36 C37 H37 118.7 . . ? C38 C37 H37 118.7 . . ? C37 C38 C33 117.59(19) . . ? C37 C38 C41 121.65(18) . . ? C33 C38 C41 120.74(18) . . ? C34 C39 H39A 109.5 . . ? C34 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C34 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C36 C40 H40A 109.5 . . ? C36 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C36 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C38 C41 H41A 109.5 . . ? C38 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C38 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C47 C42 C43 121.35(18) . . ? C47 C42 N4 120.06(17) . . ? C43 C42 N4 118.43(18) . . ? C42 C43 C44 117.86(19) . . ? C42 C43 C48 120.64(18) . . ? C44 C43 C48 121.5(2) . . ? C45 C44 C43 122.2(2) . . ? C45 C44 H44 118.9 . . ? C43 C44 H44 118.9 . . ? C46 C45 C44 117.9(2) . . ? C46 C45 C49 120.6(2) . . ? C44 C45 C49 121.5(2) . . ? C45 C46 C47 122.3(2) . . ? C45 C46 H46 118.8 . . ? C47 C46 H46 118.8 . . ? C46 C47 C42 118.37(19) . . ? C46 C47 C50 120.8(2) . . ? C42 C47 C50 120.83(19) . . ? C43 C48 H48A 109.5 . . ? C43 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C43 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C45 C49 H49A 109.5 . . ? C45 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C45 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C47 C50 H50A 109.5 . . ? C47 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C47 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C1 N1 C15 118.13(16) . . ? C6 N2 C24 117.60(16) . . ? C7 N3 C33 117.19(16) . . ? C14 N4 C42 119.03(16) . . ? 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 N1 C1 C2 C3 -3.4(4) . . . . ? C14 C1 C2 C3 -179.4(2) . . . . ? N1 C1 C2 C12 173.9(2) . . . . ? C14 C1 C2 C12 -2.08(19) . . . . ? C12 C2 C3 C4 -0.9(3) . . . . ? C1 C2 C3 C4 176.2(2) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C11 0.4(3) . . . . ? C3 C4 C5 C6 -174.9(2) . . . . ? C4 C5 C6 N2 1.4(4) . . . . ? C11 C5 C6 N2 -174.3(2) . . . . ? C4 C5 C6 C7 178.5(2) . . . . ? C11 C5 C6 C7 2.8(2) . . . . ? N2 C6 C7 N3 -4.6(3) . . . . ? C5 C6 C7 N3 177.93(18) . . . . ? N2 C6 C7 C8 173.91(18) . . . . ? C5 C6 C7 C8 -3.5(2) . . . . ? N3 C7 C8 C9 3.7(4) . . . . ? C6 C7 C8 C9 -174.7(2) . . . . ? N3 C7 C8 C11 -178.8(2) . . . . ? C6 C7 C8 C11 2.8(2) . . . . ? C11 C8 C9 C10 0.5(3) . . . . ? C7 C8 C9 C10 177.7(2) . . . . ? C8 C9 C10 C13 -0.7(3) . . . . ? C9 C8 C11 C12 0.0(3) . . . . ? C7 C8 C11 C12 -178.04(18) . . . . ? C9 C8 C11 C5 176.95(18) . . . . ? C7 C8 C11 C5 -1.1(2) . . . . ? C4 C5 C11 C12 -1.0(3) . . . . ? C6 C5 C11 C12 175.77(17) . . . . ? C4 C5 C11 C8 -177.86(17) . . . . ? C6 C5 C11 C8 -1.1(2) . . . . ? C8 C11 C12 C2 177.35(17) . . . . ? C5 C11 C12 C2 0.6(3) . . . . ? C8 C11 C12 C13 -0.3(3) . . . . ? C5 C11 C12 C13 -177.08(18) . . . . ? C3 C2 C12 C11 0.4(3) . . . . ? C1 C2 C12 C11 -177.65(18) . . . . ? C3 C2 C12 C13 178.14(18) . . . . ? C1 C2 C12 C13 0.1(2) . . . . ? C9 C10 C13 C12 0.4(3) . . . . ? C9 C10 C13 C14 -179.1(2) . . . . ? C11 C12 C13 C10 0.1(3) . . . . ? C2 C12 C13 C10 -177.70(18) . . . . ? C11 C12 C13 C14 179.72(18) . . . . ? C2 C12 C13 C14 1.9(2) . . . . ? C10 C13 C14 N4 -3.7(4) . . . . ? C12 C13 C14 N4 176.7(2) . . . . ? C10 C13 C14 C1 176.5(2) . . . . ? C12 C13 C14 C1 -3.1(2) . . . . ? N1 C1 C14 N4 6.8(3) . . . . ? C2 C1 C14 N4 -176.58(18) . . . . ? N1 C1 C14 C13 -173.33(18) . . . . ? C2 C1 C14 C13 3.2(2) . . . . ? C20 C15 C16 C17 -0.9(3) . . . . ? N1 C15 C16 C17 -177.82(18) . . . . ? C20 C15 C16 C21 -179.2(2) . . . . ? N1 C15 C16 C21 3.8(3) . . . . ? C15 C16 C17 C18 -0.3(3) . . . . ? C21 C16 C17 C18 178.1(2) . . . . ? C16 C17 C18 C19 0.3(3) . . . . ? C16 C17 C18 C22 179.9(2) . . . . ? C17 C18 C19 C20 0.9(3) . . . . ? C22 C18 C19 C20 -178.8(2) . . . . ? C18 C19 C20 C15 -1.9(3) . . . . ? C18 C19 C20 C23 178.9(2) . . . . ? C16 C15 C20 C19 1.9(3) . . . . ? N1 C15 C20 C19 178.82(17) . . . . ? C16 C15 C20 C23 -178.9(2) . . . . ? N1 C15 C20 C23 -2.1(3) . . . . ? C29 C24 C25 C26 2.0(3) . . . . ? N2 C24 C25 C26 -179.98(17) . . . . ? C29 C24 C25 C30 -178.03(19) . . . . ? N2 C24 C25 C30 -0.1(3) . . . . ? C24 C25 C26 C27 -1.4(3) . . . . ? C30 C25 C26 C27 178.7(2) . . . . ? C25 C26 C27 C28 -0.1(3) . . . . ? C25 C26 C27 C31 -179.2(2) . . . . ? C26 C27 C28 C29 1.0(3) . . . . ? C31 C27 C28 C29 -179.93(19) . . . . ? C27 C28 C29 C24 -0.3(3) . . . . ? C27 C28 C29 C32 179.08(19) . . . . ? C25 C24 C29 C28 -1.2(3) . . . . ? N2 C24 C29 C28 -179.15(16) . . . . ? C25 C24 C29 C32 179.35(19) . . . . ? N2 C24 C29 C32 1.4(3) . . . . ? C38 C33 C34 C35 -1.8(3) . . . . ? N3 C33 C34 C35 -179.49(17) . . . . ? C38 C33 C34 C39 179.63(19) . . . . ? N3 C33 C34 C39 1.9(3) . . . . ? C33 C34 C35 C36 1.2(3) . . . . ? C39 C34 C35 C36 179.7(2) . . . . ? C34 C35 C36 C37 0.1(3) . . . . ? C34 C35 C36 C40 179.6(2) . . . . ? C35 C36 C37 C38 -0.8(3) . . . . ? C40 C36 C37 C38 179.7(2) . . . . ? C36 C37 C38 C33 0.3(3) . . . . ? C36 C37 C38 C41 -178.5(2) . . . . ? C34 C33 C38 C37 1.1(3) . . . . ? N3 C33 C38 C37 178.77(17) . . . . ? C34 C33 C38 C41 179.88(19) . . . . ? N3 C33 C38 C41 -2.5(3) . . . . ? C47 C42 C43 C44 -0.3(3) . . . . ? N4 C42 C43 C44 175.02(18) . . . . ? C47 C42 C43 C48 179.1(2) . . . . ? N4 C42 C43 C48 -5.6(3) . . . . ? C42 C43 C44 C45 0.0(3) . . . . ? C48 C43 C44 C45 -179.4(2) . . . . ? C43 C44 C45 C46 0.3(4) . . . . ? C43 C44 C45 C49 -179.0(2) . . . . ? C44 C45 C46 C47 -0.4(3) . . . . ? C49 C45 C46 C47 178.9(2) . . . . ? C45 C46 C47 C42 0.1(3) . . . . ? C45 C46 C47 C50 178.4(2) . . . . ? C43 C42 C47 C46 0.2(3) . . . . ? N4 C42 C47 C46 -175.00(17) . . . . ? C43 C42 C47 C50 -178.09(19) . . . . ? N4 C42 C47 C50 6.7(3) . . . . ? C2 C1 N1 C15 2.0(3) . . . . ? C14 C1 N1 C15 177.59(17) . . . . ? C16 C15 N1 C1 -100.9(2) . . . . ? C20 C15 N1 C1 82.1(2) . . . . ? C5 C6 N2 C24 0.1(3) . . . . ? C7 C6 N2 C24 -176.61(16) . . . . ? C25 C24 N2 C6 92.4(2) . . . . ? C29 C24 N2 C6 -89.6(2) . . . . ? C8 C7 N3 C33 0.7(3) . . . . ? C6 C7 N3 C33 178.85(17) . . . . ? C34 C33 N3 C7 -95.7(2) . . . . ? C38 C33 N3 C7 86.6(2) . . . . ? C13 C14 N4 C42 2.9(3) . . . . ? C1 C14 N4 C42 -177.33(16) . . . . ? C47 C42 N4 C14 -95.4(2) . . . . ? C43 C42 N4 C14 89.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.346 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.067 # Attachment 'Compound 2_New.cif' data_squeezed_a _database_code_depnum_ccdc_archive 'CCDC 670789' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _publ_section_synopsis ; ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Sluis, P. v.d. & Spek, A. L. (1990). SQUEEZE. Acta Cryst. A46, 194-201. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C62 H74 N4, 2(C H Cl3)' _chemical_formula_sum 'C64 H74 Cl6 N4' _chemical_formula_weight 1112.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall -P2yn 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 12.673(3) _cell_length_b 15.048(3) _cell_length_c 18.514(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.68(3) _cell_angle_gamma 90.00 _cell_volume 3499.1(12) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.055 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.282 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min .972 _exptl_absorpt_correction_T_max .977 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13524 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0810 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.44 _reflns_number_total 7960 _reflns_number_gt 4552 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.1422P)^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 7960 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1169 _refine_ls_R_factor_gt 0.0692 _refine_ls_wR_factor_ref 0.2336 _refine_ls_wR_factor_gt 0.2072 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 C6 C 0.6356(2) 0.54614(19) 0.10404(14) 0.0267(6) Uani 1 1 d . . . H6 H 0.6780 0.5537 0.1486 0.032 Uiso 1 1 calc R . . C7 C 0.3476(2) 0.3994(2) -0.04360(14) 0.0280(6) Uani 1 1 d . . . H7 H 0.2934 0.3574 -0.0491 0.034 Uiso 1 1 calc R . . C32 C -0.0239(2) 0.3090(2) -0.22893(16) 0.0357(7) Uani 1 1 d . . . H32 H -0.0241 0.2578 -0.2617 0.043 Uiso 1 1 calc R . . Cl1 Cl 0.06702(7) 0.38784(7) -0.25353(5) 0.0535(3) Uani 1 1 d . . . Cl2 Cl -0.15360(7) 0.35375(7) -0.23766(5) 0.0499(3) Uani 1 1 d . . . Cl3 Cl 0.01605(8) 0.27290(7) -0.13923(4) 0.0553(3) Uani 1 1 d . . . C1 C 0.4223(2) 0.36454(18) 0.09629(14) 0.0234(6) Uani 1 1 d . . . C2 C 0.4112(2) 0.40816(18) 0.02368(13) 0.0233(6) Uani 1 1 d . . . C3 C 0.4921(2) 0.47363(19) 0.02902(14) 0.0251(6) Uani 1 1 d . . . C4 C 0.5561(2) 0.48171(19) 0.09667(13) 0.0255(6) Uani 1 1 d . . . C5 C 0.5150(2) 0.41228(18) 0.14403(13) 0.0223(6) Uani 1 1 d . . . C8 C 0.2807(2) 0.26347(19) 0.08187(13) 0.0249(6) Uani 1 1 d . . . C9 C 0.1812(2) 0.3073(2) 0.07607(14) 0.0297(7) Uani 1 1 d . . . C10 C 0.0939(2) 0.2622(2) 0.03933(16) 0.0377(8) Uani 1 1 d . . . H10 H 0.0270 0.2886 0.0345 0.045 Uiso 1 1 calc R . . C11 C 0.1055(3) 0.1781(2) 0.00971(16) 0.0405(8) Uani 1 1 d . . . H11 H 0.0463 0.1494 -0.0148 0.049 Uiso 1 1 calc R . . C12 C 0.2025(3) 0.1375(2) 0.01621(15) 0.0367(7) Uani 1 1 d . . . H12 H 0.2088 0.0817 -0.0044 0.044 Uiso 1 1 calc R . . C13 C 0.2922(2) 0.1787(2) 0.05342(14) 0.0301(7) Uani 1 1 d . . . C14 C 0.4009(2) 0.1346(2) 0.06316(16) 0.0361(7) Uani 1 1 d . . . H14 H 0.4408 0.1590 0.1078 0.043 Uiso 1 1 calc R . . C15 C 0.4620(3) 0.1583(3) 0.00083(18) 0.0463(8) Uani 1 1 d . . . H15A H 0.4261 0.1339 -0.0437 0.069 Uiso 1 1 calc R . . H15B H 0.5326 0.1341 0.0101 0.069 Uiso 1 1 calc R . . H15C H 0.4660 0.2217 -0.0034 0.069 Uiso 1 1 calc R . . C16 C 0.3957(3) 0.0343(2) 0.07312(19) 0.0488(9) Uani 1 1 d . . . H16A H 0.3717 0.0213 0.1190 0.073 Uiso 1 1 calc R . . H16B H 0.4653 0.0093 0.0723 0.073 Uiso 1 1 calc R . . H16C H 0.3471 0.0092 0.0343 0.073 Uiso 1 1 calc R . . C17 C 0.1697(2) 0.3954(2) 0.11295(16) 0.0354(7) Uani 1 1 d . . . H17 H 0.2345 0.4297 0.1095 0.042 Uiso 1 1 calc R . . C18 C 0.0761(3) 0.4502(3) 0.0781(2) 0.0607(11) Uani 1 1 d . . . H18A H 0.0796 0.4560 0.0268 0.091 Uiso 1 1 calc R . . H18B H 0.0787 0.5081 0.1001 0.091 Uiso 1 1 calc R . . H18C H 0.0109 0.4212 0.0853 0.091 Uiso 1 1 calc R . . C19 C 0.1624(3) 0.3806(3) 0.19459(18) 0.0536(10) Uani 1 1 d . . . H19A H 0.0972 0.3503 0.1999 0.080 Uiso 1 1 calc R . . H19B H 0.1638 0.4370 0.2190 0.080 Uiso 1 1 calc R . . H19C H 0.2217 0.3453 0.2157 0.080 Uiso 1 1 calc R . . C20 C 0.6169(2) 0.43939(19) 0.25717(13) 0.0248(6) Uani 1 1 d . . . C21 C 0.7210(2) 0.4078(2) 0.27240(14) 0.0297(7) Uani 1 1 d . . . C22 C 0.7911(2) 0.4563(2) 0.32156(16) 0.0355(7) Uani 1 1 d . . . H22 H 0.8619 0.4385 0.3305 0.043 Uiso 1 1 calc R . . C23 C 0.7599(2) 0.5291(2) 0.35710(16) 0.0379(8) Uani 1 1 d . . . H23 H 0.8086 0.5592 0.3905 0.045 Uiso 1 1 calc R . . C24 C 0.6545(2) 0.5582(2) 0.34303(16) 0.0367(7) Uani 1 1 d . . . H24 H 0.6333 0.6081 0.3671 0.044 Uiso 1 1 calc R . . C25 C 0.5803(2) 0.5133(2) 0.29315(14) 0.0293(6) Uani 1 1 d . . . C26 C 0.7566(2) 0.3253(2) 0.23668(16) 0.0384(8) Uani 1 1 d . . . H26 H 0.6936 0.2974 0.2095 0.046 Uiso 1 1 calc R . . C27 C 0.8079(3) 0.2582(3) 0.29173(19) 0.0480(9) Uani 1 1 d . . . H27A H 0.8707 0.2836 0.3185 0.072 Uiso 1 1 calc R . . H27B H 0.8268 0.2059 0.2667 0.072 Uiso 1 1 calc R . . H27C H 0.7586 0.2427 0.3248 0.072 Uiso 1 1 calc R . . C28 C 0.8347(4) 0.3484(3) 0.1817(2) 0.0723(13) Uani 1 1 d . . . H28A H 0.7974 0.3805 0.1413 0.109 Uiso 1 1 calc R . . H28B H 0.8633 0.2946 0.1643 0.109 Uiso 1 1 calc R . . H28C H 0.8917 0.3843 0.2053 0.109 Uiso 1 1 calc R . . C29 C 0.4638(2) 0.5405(2) 0.28185(18) 0.0390(8) Uani 1 1 d . . . H29 H 0.4365 0.5294 0.2306 0.047 Uiso 1 1 calc R . . C30 C 0.4465(3) 0.6383(3) 0.2968(2) 0.0549(10) Uani 1 1 d . . . H30A H 0.3719 0.6517 0.2873 0.082 Uiso 1 1 calc R . . H30B H 0.4844 0.6737 0.2656 0.082 Uiso 1 1 calc R . . H30C H 0.4724 0.6512 0.3468 0.082 Uiso 1 1 calc R . . C31 C 0.4008(3) 0.4830(3) 0.3274(3) 0.0674(12) Uani 1 1 d . . . H31A H 0.4023 0.4225 0.3110 0.101 Uiso 1 1 calc R . . H31B H 0.3285 0.5035 0.3225 0.101 Uiso 1 1 calc R . . H31C H 0.4316 0.4864 0.3776 0.101 Uiso 1 1 calc R . . N1 N 0.37138(17) 0.30362(15) 0.12389(11) 0.0240(5) Uani 1 1 d . . . N2 N 0.53917(17) 0.38997(16) 0.20996(11) 0.0240(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C6 0.0291(14) 0.0302(16) 0.0198(12) 0.0004(12) -0.0006(11) -0.0044(12) C7 0.0267(14) 0.0278(16) 0.0284(13) -0.0024(12) 0.0003(11) -0.0054(12) C32 0.0389(17) 0.0389(19) 0.0297(14) -0.0001(13) 0.0057(13) -0.0016(14) Cl1 0.0497(5) 0.0591(6) 0.0504(5) 0.0107(4) 0.0018(4) -0.0133(4) Cl2 0.0439(5) 0.0574(6) 0.0491(5) -0.0009(4) 0.0093(4) 0.0081(4) Cl3 0.0610(6) 0.0668(7) 0.0378(4) 0.0117(4) 0.0059(4) 0.0044(5) C1 0.0261(13) 0.0221(14) 0.0214(12) 0.0004(11) 0.0010(11) 0.0000(11) C2 0.0252(13) 0.0253(15) 0.0193(12) -0.0001(11) 0.0025(10) -0.0026(12) C3 0.0252(13) 0.0269(15) 0.0230(12) -0.0011(11) 0.0026(11) -0.0009(12) C4 0.0289(14) 0.0249(15) 0.0223(12) 0.0005(11) 0.0020(11) -0.0006(12) C5 0.0201(13) 0.0230(14) 0.0241(12) -0.0008(11) 0.0040(10) -0.0001(11) C8 0.0274(14) 0.0271(15) 0.0202(12) 0.0047(11) 0.0036(10) -0.0042(12) C9 0.0311(15) 0.0344(17) 0.0228(13) 0.0072(12) 0.0005(11) -0.0010(13) C10 0.0303(16) 0.044(2) 0.0364(15) 0.0036(15) -0.0029(13) -0.0023(15) C11 0.0361(17) 0.046(2) 0.0361(16) 0.0019(15) -0.0063(14) -0.0132(16) C12 0.0462(19) 0.0328(18) 0.0299(14) -0.0049(13) 0.0003(13) -0.0061(15) C13 0.0324(15) 0.0319(17) 0.0257(13) 0.0019(12) 0.0027(12) -0.0014(13) C14 0.0383(17) 0.0324(18) 0.0359(16) -0.0054(13) -0.0007(13) 0.0026(14) C15 0.0444(19) 0.048(2) 0.0468(18) -0.0038(16) 0.0088(16) 0.0060(17) C16 0.056(2) 0.036(2) 0.053(2) -0.0030(16) 0.0024(17) 0.0082(17) C17 0.0331(16) 0.0320(18) 0.0404(16) 0.0013(14) 0.0028(13) 0.0021(14) C18 0.067(3) 0.052(2) 0.061(2) 0.007(2) -0.0007(19) 0.025(2) C19 0.073(3) 0.045(2) 0.0426(19) -0.0022(16) 0.0100(18) 0.012(2) C20 0.0294(14) 0.0271(15) 0.0179(11) 0.0027(11) 0.0033(10) -0.0053(12) C21 0.0295(15) 0.0346(17) 0.0246(13) 0.0051(12) 0.0020(11) 0.0004(13) C22 0.0281(15) 0.0402(19) 0.0365(15) 0.0049(14) -0.0021(13) 0.0003(14) C23 0.0385(17) 0.042(2) 0.0301(15) 0.0006(14) -0.0052(13) -0.0125(15) C24 0.0415(17) 0.0356(18) 0.0319(14) -0.0042(14) 0.0014(13) -0.0011(15) C25 0.0330(15) 0.0310(16) 0.0237(13) 0.0009(12) 0.0033(11) -0.0027(13) C26 0.0317(16) 0.047(2) 0.0357(16) -0.0017(15) 0.0008(13) 0.0051(14) C27 0.053(2) 0.041(2) 0.0504(19) 0.0035(17) 0.0066(16) 0.0091(17) C28 0.095(3) 0.060(3) 0.071(3) 0.020(2) 0.046(2) 0.028(3) C29 0.0322(16) 0.041(2) 0.0434(16) -0.0131(15) 0.0049(13) 0.0035(14) C30 0.043(2) 0.053(2) 0.069(2) -0.0032(19) 0.0082(18) 0.0124(18) C31 0.046(2) 0.054(3) 0.108(3) -0.004(2) 0.030(2) 0.001(2) N1 0.0250(11) 0.0206(12) 0.0263(11) 0.0004(9) 0.0037(9) -0.0017(10) N2 0.0241(11) 0.0274(13) 0.0200(10) 0.0002(9) 0.0009(9) 0.0000(10) _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 C6 C4 1.392(4) . ? C6 C7 1.425(4) 3_665 ? C6 H6 0.9300 . ? C7 C2 1.396(4) . ? C7 C6 1.425(4) 3_665 ? C7 H7 0.9300 . ? C32 Cl1 1.756(3) . ? C32 Cl3 1.756(3) . ? C32 Cl2 1.764(3) . ? C32 H32 0.9800 . ? C1 N1 1.268(3) . ? C1 C2 1.486(4) . ? C1 C5 1.549(4) . ? C2 C3 1.415(4) . ? C3 C3 1.372(5) 3_665 ? C3 C4 1.404(3) . ? C4 C5 1.501(4) . ? C5 N2 1.264(3) . ? C8 C13 1.396(4) . ? C8 C9 1.414(4) . ? C8 N1 1.433(3) . ? C9 C10 1.395(4) . ? C9 C17 1.507(4) . ? C10 C11 1.395(5) . ? C10 H10 0.9300 . ? C11 C12 1.364(5) . ? C11 H11 0.9300 . ? C12 C13 1.394(4) . ? C12 H12 0.9300 . ? C13 C14 1.518(4) . ? C14 C15 1.515(5) . ? C14 C16 1.523(5) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.515(4) . ? C17 C19 1.543(5) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.396(4) . ? C20 C25 1.406(4) . ? C20 N2 1.434(3) . ? C21 C22 1.391(4) . ? C21 C26 1.504(4) . ? C22 C23 1.363(5) . ? C22 H22 0.9300 . ? C23 C24 1.397(5) . ? C23 H23 0.9300 . ? C24 C25 1.401(4) . ? C24 H24 0.9300 . ? C25 C29 1.520(4) . ? C26 C27 1.517(5) . ? C26 C28 1.551(5) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C31 1.508(5) . ? C29 C30 1.519(5) . ? C29 H29 0.9800 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C6 C7 120.3(2) . 3_665 ? C4 C6 H6 119.8 . . ? C7 C6 H6 119.8 3_665 . ? C2 C7 C6 121.2(3) . 3_665 ? C2 C7 H7 119.4 . . ? C6 C7 H7 119.4 3_665 . ? Cl1 C32 Cl3 109.73(17) . . ? Cl1 C32 Cl2 110.72(18) . . ? Cl3 C32 Cl2 110.63(17) . . ? Cl1 C32 H32 108.6 . . ? Cl3 C32 H32 108.6 . . ? Cl2 C32 H32 108.6 . . ? N1 C1 C2 133.8(2) . . ? N1 C1 C5 119.6(2) . . ? C2 C1 C5 106.5(2) . . ? C7 C2 C3 117.0(2) . . ? C7 C2 C1 137.7(3) . . ? C3 C2 C1 105.3(2) . . ? C3 C3 C4 121.4(3) 3_665 . ? C3 C3 C2 121.9(3) 3_665 . ? C4 C3 C2 116.7(2) . . ? C6 C4 C3 118.2(2) . . ? C6 C4 C5 136.9(2) . . ? C3 C4 C5 104.9(2) . . ? N2 C5 C4 133.7(2) . . ? N2 C5 C1 119.7(2) . . ? C4 C5 C1 106.6(2) . . ? C13 C8 C9 122.3(3) . . ? C13 C8 N1 118.3(2) . . ? C9 C8 N1 119.1(3) . . ? C10 C9 C8 116.8(3) . . ? C10 C9 C17 122.0(3) . . ? C8 C9 C17 121.0(3) . . ? C11 C10 C9 121.0(3) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 120.9(3) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 120.7(3) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 118.3(3) . . ? C12 C13 C14 122.1(3) . . ? C8 C13 C14 119.6(3) . . ? C15 C14 C13 110.8(3) . . ? C15 C14 C16 111.1(3) . . ? C13 C14 C16 113.2(3) . . ? C15 C14 H14 107.1 . . ? C13 C14 H14 107.1 . . ? C16 C14 H14 107.1 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C9 C17 C18 113.8(3) . . ? C9 C17 C19 109.8(3) . . ? C18 C17 C19 110.5(3) . . ? C9 C17 H17 107.5 . . ? C18 C17 H17 107.5 . . ? C19 C17 H17 107.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 122.4(2) . . ? C21 C20 N2 120.0(3) . . ? C25 C20 N2 117.1(2) . . ? C22 C21 C20 117.2(3) . . ? C22 C21 C26 121.2(3) . . ? C20 C21 C26 121.6(3) . . ? C23 C22 C21 122.5(3) . . ? C23 C22 H22 118.7 . . ? C21 C22 H22 118.7 . . ? C22 C23 C24 119.6(3) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C23 C24 C25 120.8(3) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C24 C25 C20 117.4(3) . . ? C24 C25 C29 121.0(3) . . ? C20 C25 C29 121.6(2) . . ? C21 C26 C27 112.4(3) . . ? C21 C26 C28 111.0(3) . . ? C27 C26 C28 109.7(3) . . ? C21 C26 H26 107.9 . . ? C27 C26 H26 107.9 . . ? C28 C26 H26 107.9 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C31 C29 C30 110.7(3) . . ? C31 C29 C25 110.2(3) . . ? C30 C29 C25 113.4(3) . . ? C31 C29 H29 107.4 . . ? C30 C29 H29 107.4 . . ? C25 C29 H29 107.4 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C1 N1 C8 120.1(2) . . ? C5 N2 C20 120.6(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 C6 C7 C2 C3 0.4(4) 3_665 . . . ? C6 C7 C2 C1 -177.3(3) 3_665 . . . ? N1 C1 C2 C7 -4.0(6) . . . . ? C5 C1 C2 C7 179.1(3) . . . . ? N1 C1 C2 C3 178.1(3) . . . . ? C5 C1 C2 C3 1.2(3) . . . . ? C7 C2 C3 C3 -0.1(5) . . . 3_665 ? C1 C2 C3 C3 178.3(3) . . . 3_665 ? C7 C2 C3 C4 -179.7(3) . . . . ? C1 C2 C3 C4 -1.2(3) . . . . ? C7 C6 C4 C3 -1.4(4) 3_665 . . . ? C7 C6 C4 C5 178.6(3) 3_665 . . . ? C3 C3 C4 C6 1.1(5) 3_665 . . . ? C2 C3 C4 C6 -179.3(3) . . . . ? C3 C3 C4 C5 -178.9(3) 3_665 . . . ? C2 C3 C4 C5 0.7(3) . . . . ? C6 C4 C5 N2 2.0(6) . . . . ? C3 C4 C5 N2 -178.0(3) . . . . ? C6 C4 C5 C1 -179.9(3) . . . . ? C3 C4 C5 C1 0.2(3) . . . . ? N1 C1 C5 N2 0.2(4) . . . . ? C2 C1 C5 N2 177.6(2) . . . . ? N1 C1 C5 C4 -178.3(2) . . . . ? C2 C1 C5 C4 -0.9(3) . . . . ? C13 C8 C9 C10 -0.9(4) . . . . ? N1 C8 C9 C10 -175.2(2) . . . . ? C13 C8 C9 C17 174.6(3) . . . . ? N1 C8 C9 C17 0.3(4) . . . . ? C8 C9 C10 C11 -0.3(4) . . . . ? C17 C9 C10 C11 -175.8(3) . . . . ? C9 C10 C11 C12 0.4(5) . . . . ? C10 C11 C12 C13 0.8(5) . . . . ? C11 C12 C13 C8 -1.9(4) . . . . ? C11 C12 C13 C14 178.6(3) . . . . ? C9 C8 C13 C12 1.9(4) . . . . ? N1 C8 C13 C12 176.3(2) . . . . ? C9 C8 C13 C14 -178.6(3) . . . . ? N1 C8 C13 C14 -4.2(4) . . . . ? C12 C13 C14 C15 90.4(4) . . . . ? C8 C13 C14 C15 -89.1(3) . . . . ? C12 C13 C14 C16 -35.2(4) . . . . ? C8 C13 C14 C16 145.4(3) . . . . ? C10 C9 C17 C18 -28.7(4) . . . . ? C8 C9 C17 C18 156.1(3) . . . . ? C10 C9 C17 C19 95.8(3) . . . . ? C8 C9 C17 C19 -79.5(4) . . . . ? C25 C20 C21 C22 -4.5(4) . . . . ? N2 C20 C21 C22 -176.7(2) . . . . ? C25 C20 C21 C26 176.1(3) . . . . ? N2 C20 C21 C26 3.9(4) . . . . ? C20 C21 C22 C23 3.5(4) . . . . ? C26 C21 C22 C23 -177.1(3) . . . . ? C21 C22 C23 C24 -1.5(5) . . . . ? C22 C23 C24 C25 0.4(5) . . . . ? C23 C24 C25 C20 -1.3(4) . . . . ? C23 C24 C25 C29 175.4(3) . . . . ? C21 C20 C25 C24 3.4(4) . . . . ? N2 C20 C25 C24 175.8(2) . . . . ? C21 C20 C25 C29 -173.2(3) . . . . ? N2 C20 C25 C29 -0.8(4) . . . . ? C22 C21 C26 C27 53.9(4) . . . . ? C20 C21 C26 C27 -126.8(3) . . . . ? C22 C21 C26 C28 -69.3(4) . . . . ? C20 C21 C26 C28 110.0(3) . . . . ? C24 C25 C29 C31 -96.4(4) . . . . ? C20 C25 C29 C31 80.1(4) . . . . ? C24 C25 C29 C30 28.4(4) . . . . ? C20 C25 C29 C30 -155.1(3) . . . . ? C2 C1 N1 C8 -1.1(5) . . . . ? C5 C1 N1 C8 175.5(2) . . . . ? C13 C8 N1 C1 104.2(3) . . . . ? C9 C8 N1 C1 -81.2(3) . . . . ? C4 C5 N2 C20 4.6(5) . . . . ? C1 C5 N2 C20 -173.3(2) . . . . ? C21 C20 N2 C5 -100.2(3) . . . . ? C25 C20 N2 C5 87.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.529 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.094 # Attachment 'Compound 3.cif' data_ccdkvkv036a _database_code_depnum_ccdc_archive 'CCDC 670790' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _publ_section_synopsis ; ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Sluis, P. v.d. & Spek, A. L. (1990). SQUEEZE. Acta Cryst. A46, 194-201. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C62 H72 Cl4 N4 Zn2, 6(C H Cl3)' _chemical_formula_sum 'C68 H78 Cl22 N4 Zn2' _chemical_formula_weight 1861.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _symmetry_space_group_name_Hall -p1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.151(5) _cell_length_b 15.312(5) _cell_length_c 23.978(5) _cell_angle_alpha 81.542(5) _cell_angle_beta 77.600(5) _cell_angle_gamma 64.858(5) _cell_volume 4260(2) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max .25 _exptl_crystal_size_mid .10 _exptl_crystal_size_min .10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1896 _exptl_absorpt_coefficient_mu 1.293 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28557 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.1193 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.46 _reflns_number_total 19305 _reflns_number_gt 9985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.1080P)^2^+1.8771P] 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 19305 _refine_ls_number_parameters 881 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1620 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.2223 _refine_ls_wR_factor_gt 0.1816 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7872(4) 0.6676(3) 0.0330(2) 0.0235(11) Uani 1 1 d . . . C2 C 0.8784(4) 0.6162(3) -0.0136(2) 0.0259(11) Uani 1 1 d . . . C3 C 0.9519(4) 0.5328(3) 0.0146(2) 0.0249(11) Uani 1 1 d . . . C4 C 0.9210(4) 0.5206(3) 0.0744(2) 0.0237(11) Uani 1 1 d . . . C5 C 0.8128(4) 0.6067(3) 0.0890(2) 0.0229(11) Uani 1 1 d . . . C6 C 0.9922(4) 0.4405(3) 0.1031(2) 0.0269(11) Uani 1 1 d . . . H6 H 0.9738 0.4315 0.1426 0.032 Uiso 1 1 calc R . . C7 C 0.9060(4) 0.6285(4) -0.0728(2) 0.0295(12) Uani 1 1 d . . . H7 H 0.8582 0.6818 -0.0926 0.035 Uiso 1 1 calc R . . C8 C 0.6547(4) 0.7907(3) -0.0183(2) 0.0271(11) Uani 1 1 d . . . C9 C 0.5869(4) 0.7582(4) -0.0403(2) 0.0321(12) Uani 1 1 d . . . C10 C 0.5521(4) 0.8029(4) -0.0920(2) 0.0356(13) Uani 1 1 d . . . H10 H 0.5090 0.7822 -0.1086 0.043 Uiso 1 1 calc R . . C11 C 0.5804(5) 0.8773(4) -0.1190(2) 0.0397(14) Uani 1 1 d . . . H11 H 0.5588 0.9047 -0.1542 0.048 Uiso 1 1 calc R . . C12 C 0.6404(5) 0.9113(4) -0.0944(2) 0.0360(13) Uani 1 1 d . . . H12 H 0.6545 0.9642 -0.1121 0.043 Uiso 1 1 calc R . . C13 C 0.6807(4) 0.8689(3) -0.0437(2) 0.0280(12) Uani 1 1 d . . . C14 C 0.5516(5) 0.6781(4) -0.0100(2) 0.0369(13) Uani 1 1 d . . . H14 H 0.5656 0.6696 0.0294 0.044 Uiso 1 1 calc R . . C15 C 0.4253(5) 0.7039(5) -0.0067(3) 0.0524(17) Uani 1 1 d . . . H15A H 0.4107 0.7025 -0.0440 0.079 Uiso 1 1 calc R . . H15B H 0.3815 0.7675 0.0068 0.079 Uiso 1 1 calc R . . H15C H 0.4041 0.6579 0.0191 0.079 Uiso 1 1 calc R . . C16 C 0.6219(5) 0.5828(4) -0.0367(3) 0.0566(18) Uani 1 1 d . . . H16A H 0.6082 0.5879 -0.0750 0.085 Uiso 1 1 calc R . . H16B H 0.6011 0.5335 -0.0146 0.085 Uiso 1 1 calc R . . H16C H 0.7013 0.5662 -0.0375 0.085 Uiso 1 1 calc R . . C17 C 0.7475(5) 0.9063(4) -0.0174(2) 0.0363(13) Uani 1 1 d . . . H17 H 0.7669 0.8670 0.0180 0.044 Uiso 1 1 calc R . . C18 C 0.8571(5) 0.8999(5) -0.0563(3) 0.0567(18) Uani 1 1 d . . . H18A H 0.9011 0.8346 -0.0672 0.085 Uiso 1 1 calc R . . H18B H 0.9000 0.9187 -0.0365 0.085 Uiso 1 1 calc R . . H18C H 0.8397 0.9422 -0.0899 0.085 Uiso 1 1 calc R . . C19 C 0.6751(6) 1.0128(4) -0.0021(3) 0.0535(17) Uani 1 1 d . . . H19A H 0.6587 1.0531 -0.0365 0.080 Uiso 1 1 calc R . . H19B H 0.7169 1.0335 0.0173 0.080 Uiso 1 1 calc R . . H19C H 0.6051 1.0175 0.0224 0.080 Uiso 1 1 calc R . . C20 C 0.7457(4) 0.5669(3) 0.1842(2) 0.0258(11) Uani 1 1 d . . . C21 C 0.7159(4) 0.4892(4) 0.1828(2) 0.0322(12) Uani 1 1 d . . . C22 C 0.7152(5) 0.4304(4) 0.2332(3) 0.0413(14) Uani 1 1 d . . . H22 H 0.6934 0.3797 0.2345 0.050 Uiso 1 1 calc R . . C23 C 0.7465(5) 0.4462(4) 0.2815(2) 0.0421(14) Uani 1 1 d . . . H23 H 0.7473 0.4054 0.3144 0.050 Uiso 1 1 calc R . . C24 C 0.7759(5) 0.5224(4) 0.2803(2) 0.0409(14) Uani 1 1 d . . . H24 H 0.7970 0.5323 0.3127 0.049 Uiso 1 1 calc R . . C25 C 0.7752(4) 0.5850(4) 0.2320(2) 0.0268(11) Uani 1 1 d . . . C26 C 0.6809(5) 0.4696(4) 0.1313(3) 0.0439(15) Uani 1 1 d . . . H26 H 0.7023 0.5080 0.0983 0.053 Uiso 1 1 calc R . . C27 C 0.7412(7) 0.3632(5) 0.1169(4) 0.079(2) Uani 1 1 d . . . H27A H 0.8222 0.3435 0.1111 0.119 Uiso 1 1 calc R . . H27B H 0.7199 0.3555 0.0827 0.119 Uiso 1 1 calc R . . H27C H 0.7191 0.3240 0.1479 0.119 Uiso 1 1 calc R . . C28 C 0.5512(6) 0.5026(6) 0.1402(3) 0.071(2) Uani 1 1 d . . . H28A H 0.5282 0.4633 0.1708 0.106 Uiso 1 1 calc R . . H28B H 0.5298 0.4962 0.1056 0.106 Uiso 1 1 calc R . . H28C H 0.5144 0.5690 0.1496 0.106 Uiso 1 1 calc R . . C29 C 0.8108(5) 0.6670(4) 0.2317(2) 0.0371(13) Uani 1 1 d . . . H29 H 0.7925 0.7081 0.1967 0.044 Uiso 1 1 calc R . . C30 C 0.9386(5) 0.6317(5) 0.2302(3) 0.0544(17) Uani 1 1 d . . . H30A H 0.9590 0.5919 0.2644 0.082 Uiso 1 1 calc R . . H30B H 0.9575 0.6862 0.2281 0.082 Uiso 1 1 calc R . . H30C H 0.9795 0.5947 0.1974 0.082 Uiso 1 1 calc R . . C31 C 0.7434(6) 0.7302(5) 0.2828(3) 0.0540(17) Uani 1 1 d . . . H31A H 0.6632 0.7543 0.2823 0.081 Uiso 1 1 calc R . . H31B H 0.7648 0.7835 0.2801 0.081 Uiso 1 1 calc R . . H31C H 0.7602 0.6921 0.3179 0.081 Uiso 1 1 calc R . . C32 C 0.0980(4) 0.1157(3) 0.4165(2) 0.0268(11) Uani 1 1 d . . . C33 C 0.0828(4) 0.0241(3) 0.4309(2) 0.0272(11) Uani 1 1 d . . . C34 C 0.1203(4) -0.0626(3) 0.4063(2) 0.0292(12) Uani 1 1 d . . . H34 H 0.1672 -0.0726 0.3707 0.035 Uiso 1 1 calc R . . C35 C 0.0869(4) -0.1375(4) 0.4357(2) 0.0287(12) Uani 1 1 d . . . H35 H 0.1116 -0.1956 0.4188 0.034 Uiso 1 1 calc R . . C36 C 0.0178(4) -0.1239(3) 0.4895(2) 0.0271(11) Uani 1 1 d . . . C37 C 0.0163(4) 0.0351(3) 0.4857(2) 0.0265(11) Uani 1 1 d . . . C38 C 0.0361(4) 0.1778(3) 0.4680(2) 0.0246(11) Uani 1 1 d . . . C39 C 0.0071(4) 0.3067(3) 0.5203(2) 0.0240(11) Uani 1 1 d . . . C40 C -0.0867(4) 0.3954(4) 0.5227(2) 0.0302(12) Uani 1 1 d . . . C41 C -0.1218(5) 0.4417(4) 0.5739(2) 0.0356(13) Uani 1 1 d . . . H41 H -0.1847 0.5007 0.5773 0.043 Uiso 1 1 calc R . . C42 C -0.0646(5) 0.4011(4) 0.6192(2) 0.0380(14) Uani 1 1 d . . . H42 H -0.0897 0.4325 0.6531 0.046 Uiso 1 1 calc R . . C43 C 0.0305(5) 0.3134(4) 0.6149(2) 0.0376(13) Uani 1 1 d . . . H43 H 0.0689 0.2880 0.6458 0.045 Uiso 1 1 calc R . . C44 C 0.0696(4) 0.2629(4) 0.5655(2) 0.0317(12) Uani 1 1 d . . . C45 C -0.1511(4) 0.4367(4) 0.4726(2) 0.0359(13) Uani 1 1 d . . . H45 H -0.0963 0.4127 0.4378 0.043 Uiso 1 1 calc R . . C46 C 0.1768(5) 0.1699(4) 0.5621(2) 0.0350(13) Uani 1 1 d . . . H46 H 0.1842 0.1400 0.5271 0.042 Uiso 1 1 calc R . . C47 C 0.2825(5) 0.1909(5) 0.5571(3) 0.0494(16) Uani 1 1 d . . . H47A H 0.2833 0.2380 0.5260 0.074 Uiso 1 1 calc R . . H47B H 0.3499 0.1324 0.5503 0.074 Uiso 1 1 calc R . . H47C H 0.2805 0.2156 0.5921 0.074 Uiso 1 1 calc R . . C48 C 0.1716(5) 0.0972(4) 0.6127(3) 0.0531(17) Uani 1 1 d . . . H48A H 0.1583 0.1264 0.6478 0.080 Uiso 1 1 calc R . . H48B H 0.2426 0.0411 0.6097 0.080 Uiso 1 1 calc R . . H48C H 0.1107 0.0785 0.6123 0.080 Uiso 1 1 calc R . . C49 C -0.2426(7) 0.4000(5) 0.4772(4) 0.074(2) Uani 1 1 d . . . H49A H -0.2095 0.3306 0.4810 0.111 Uiso 1 1 calc R . . H49B H -0.2769 0.4213 0.4434 0.111 Uiso 1 1 calc R . . H49C H -0.2998 0.4247 0.5101 0.111 Uiso 1 1 calc R . . C50 C -0.1997(6) 0.5461(4) 0.4661(3) 0.0537(17) Uani 1 1 d . . . H50A H -0.2512 0.5722 0.5003 0.081 Uiso 1 1 calc R . . H50B H -0.2398 0.5682 0.4342 0.081 Uiso 1 1 calc R . . H50C H -0.1387 0.5672 0.4594 0.081 Uiso 1 1 calc R . . C51 C 0.2188(4) 0.0883(3) 0.3268(2) 0.0261(11) Uani 1 1 d . . . C52 C 0.3357(4) 0.0336(4) 0.3267(2) 0.0329(12) Uani 1 1 d . . . C53 C 0.3971(5) -0.0254(4) 0.2813(2) 0.0405(14) Uani 1 1 d . . . H53 H 0.4746 -0.0631 0.2799 0.049 Uiso 1 1 calc R . . C54 C 0.3442(5) -0.0284(4) 0.2386(2) 0.0416(15) Uani 1 1 d . . . H54 H 0.3861 -0.0692 0.2091 0.050 Uiso 1 1 calc R . . C55 C 0.2303(5) 0.0281(4) 0.2386(2) 0.0374(13) Uani 1 1 d . . . H55 H 0.1963 0.0250 0.2091 0.045 Uiso 1 1 calc R . . C56 C 0.1644(4) 0.0904(4) 0.2827(2) 0.0304(12) Uani 1 1 d . . . C57 C 0.3939(5) 0.0362(4) 0.3745(3) 0.0421(14) Uani 1 1 d . . . H57 H 0.3457 0.0966 0.3932 0.051 Uiso 1 1 calc R . . C58 C 0.5105(5) 0.0375(5) 0.3537(3) 0.0586(18) Uani 1 1 d . . . H58A H 0.5623 -0.0232 0.3383 0.088 Uiso 1 1 calc R . . H58B H 0.5378 0.0477 0.3852 0.088 Uiso 1 1 calc R . . H58C H 0.5052 0.0888 0.3246 0.088 Uiso 1 1 calc R . . C59 C 0.4010(6) -0.0460(6) 0.4200(3) 0.066(2) Uani 1 1 d . . . H59A H 0.3260 -0.0438 0.4344 0.099 Uiso 1 1 calc R . . H59B H 0.4329 -0.0393 0.4507 0.099 Uiso 1 1 calc R . . H59C H 0.4487 -0.1067 0.4034 0.099 Uiso 1 1 calc R . . C60 C 0.0430(4) 0.1591(4) 0.2779(2) 0.0381(14) Uani 1 1 d . . . H60 H 0.0127 0.1986 0.3112 0.046 Uiso 1 1 calc R . . C61 C -0.0329(6) 0.1050(5) 0.2800(3) 0.065(2) Uani 1 1 d . . . H61A H -0.0018 0.0615 0.2497 0.098 Uiso 1 1 calc R . . H61B H -0.1084 0.1507 0.2753 0.098 Uiso 1 1 calc R . . H61C H -0.0359 0.0690 0.3161 0.098 Uiso 1 1 calc R . . C62 C 0.0368(6) 0.2277(5) 0.2247(3) 0.0584(18) Uani 1 1 d . . . H62A H 0.0889 0.2573 0.2228 0.088 Uiso 1 1 calc R . . H62B H -0.0393 0.2768 0.2263 0.088 Uiso 1 1 calc R . . H62C H 0.0570 0.1921 0.1913 0.088 Uiso 1 1 calc R . . C63 C 0.1923(5) 0.7945(4) 0.2190(3) 0.0479(16) Uani 1 1 d . . . H63 H 0.2641 0.7976 0.2215 0.057 Uiso 1 1 calc R . . C64 C 0.0757(5) 0.7500(4) 0.0742(3) 0.0520(17) Uani 1 1 d . . . H64 H 0.1112 0.7470 0.1068 0.062 Uiso 1 1 calc R . . C65 C 0.4635(6) 0.6312(6) 0.3348(3) 0.069(2) Uani 1 1 d . . . H65 H 0.5217 0.5745 0.3151 0.083 Uiso 1 1 calc R . . C66 C 0.7556(6) 0.0430(5) 0.1740(3) 0.0548(17) Uani 1 1 d . . . H66 H 0.7265 0.0079 0.1552 0.066 Uiso 1 1 calc R . . C67 C 0.5674(7) 0.2595(5) 0.4054(4) 0.075(2) Uani 1 1 d . . . H67 H 0.5018 0.2522 0.3969 0.090 Uiso 1 1 calc R . . C68 C 0.2972(7) 0.3699(5) 0.2527(3) 0.071(2) Uani 1 1 d . . . H68 H 0.2370 0.3941 0.2858 0.086 Uiso 1 1 calc R . . N1 N 0.6932(3) 0.7423(3) 0.03425(16) 0.0254(9) Uani 1 1 d . . . N2 N 0.7397(3) 0.6320(3) 0.13373(17) 0.0250(9) Uani 1 1 d . . . N3 N 0.1550(3) 0.1464(3) 0.37526(16) 0.0250(9) Uani 1 1 d . . . N4 N 0.0458(3) 0.2570(3) 0.46799(16) 0.0246(9) Uani 1 1 d . . . Cl1 Cl 0.64292(11) 0.88431(9) 0.15000(6) 0.0403(3) Uani 1 1 d . . . Cl2 Cl 0.43679(12) 0.78078(12) 0.13288(7) 0.0498(4) Uani 1 1 d . . . Cl3 Cl 0.03268(13) 0.39045(10) 0.32909(6) 0.0446(4) Uani 1 1 d . . . Cl4 Cl 0.29084(12) 0.29568(10) 0.40401(6) 0.0419(4) Uani 1 1 d . . . Cl5 Cl 0.4213(3) 0.3803(3) 0.26414(13) 0.1427(13) Uani 1 1 d . . . Cl6 Cl 0.32789(17) 0.24898(12) 0.24864(8) 0.0690(5) Uani 1 1 d . . . Cl7 Cl 0.2497(2) 0.43925(18) 0.19265(12) 0.1198(10) Uani 1 1 d . . . Cl8 Cl -0.07258(13) 0.79264(13) 0.09741(7) 0.0576(4) Uani 1 1 d . . . Cl9 Cl 0.1284(2) 0.63342(18) 0.05125(15) 0.1261(12) Uani 1 1 d . . . Cl10 Cl 0.10900(17) 0.82851(17) 0.02075(9) 0.0858(7) Uani 1 1 d . . . Cl11 Cl 0.22171(15) 0.67716(12) 0.20315(8) 0.0641(5) Uani 1 1 d . . . Cl12 Cl 0.10085(15) 0.82280(14) 0.28517(7) 0.0687(5) Uani 1 1 d . . . Cl13 Cl 0.13040(14) 0.87951(12) 0.16490(7) 0.0547(4) Uani 1 1 d . . . Cl14 Cl 0.82001(17) -0.03070(15) 0.22991(9) 0.0755(6) Uani 1 1 d . . . Cl15 Cl 0.8559(2) 0.07441(16) 0.12349(9) 0.0894(7) Uani 1 1 d . . . Cl16 Cl 0.64158(17) 0.14885(16) 0.19991(9) 0.0836(6) Uani 1 1 d . . . Cl17 Cl 0.5264(2) 0.38190(18) 0.41187(14) 0.1094(9) Uani 1 1 d . . . Cl18 Cl 0.5990(6) 0.1948(3) 0.46494(18) 0.242(3) Uani 1 1 d . . . Cl19 Cl 0.6750(3) 0.2198(2) 0.34862(15) 0.1630(16) Uani 1 1 d . . . Cl21 Cl 0.3348(2) 0.61379(18) 0.35358(11) 0.0960(7) Uani 1 1 d . . . Cl22 Cl 0.5089(2) 0.6379(2) 0.39535(12) 0.1195(10) Uani 1 1 d . . . Cl23 Cl 0.4437(3) 0.7281(4) 0.2886(2) 0.245(3) Uani 1 1 d . . . Zn1 Zn 0.60928(5) 0.77280(4) 0.11903(2) 0.02888(17) Uani 1 1 d . . . Zn2 Zn 0.13745(5) 0.28678(4) 0.38875(3) 0.03037(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.022(2) 0.023(3) 0.023(3) -0.003(2) -0.001(2) -0.008(2) C2 0.024(3) 0.026(3) 0.023(3) -0.003(2) -0.002(2) -0.006(2) C3 0.025(2) 0.023(3) 0.027(3) 0.000(2) -0.005(2) -0.010(2) C4 0.026(3) 0.021(3) 0.022(3) -0.001(2) -0.002(2) -0.009(2) C5 0.025(3) 0.019(2) 0.024(3) -0.001(2) -0.002(2) -0.011(2) C6 0.033(3) 0.022(3) 0.019(3) 0.003(2) -0.001(2) -0.008(2) C7 0.036(3) 0.025(3) 0.022(3) 0.002(2) -0.010(2) -0.007(2) C8 0.024(3) 0.024(3) 0.023(3) -0.002(2) -0.001(2) 0.000(2) C9 0.031(3) 0.026(3) 0.035(3) -0.005(2) -0.005(2) -0.006(2) C10 0.036(3) 0.032(3) 0.036(3) -0.004(3) -0.014(3) -0.006(2) C11 0.042(3) 0.037(3) 0.032(3) 0.003(3) -0.013(3) -0.006(3) C12 0.045(3) 0.027(3) 0.030(3) 0.004(2) -0.005(3) -0.011(3) C13 0.024(3) 0.023(3) 0.026(3) 0.003(2) -0.004(2) -0.002(2) C14 0.044(3) 0.033(3) 0.037(3) -0.002(3) -0.008(3) -0.018(3) C15 0.044(4) 0.050(4) 0.066(4) 0.001(3) -0.010(3) -0.024(3) C16 0.054(4) 0.040(4) 0.075(5) -0.009(3) 0.000(3) -0.023(3) C17 0.041(3) 0.033(3) 0.037(3) 0.005(3) -0.011(3) -0.017(3) C18 0.046(4) 0.065(4) 0.066(5) -0.005(4) -0.007(3) -0.030(3) C19 0.064(4) 0.044(4) 0.057(4) -0.010(3) -0.011(3) -0.024(3) C20 0.023(2) 0.020(3) 0.026(3) 0.001(2) 0.001(2) -0.005(2) C21 0.032(3) 0.034(3) 0.024(3) -0.001(2) 0.002(2) -0.011(2) C22 0.041(3) 0.033(3) 0.046(4) 0.000(3) 0.003(3) -0.017(3) C23 0.050(4) 0.040(3) 0.028(3) 0.014(3) -0.007(3) -0.016(3) C24 0.041(3) 0.045(4) 0.031(3) -0.001(3) -0.003(3) -0.013(3) C25 0.025(3) 0.029(3) 0.023(3) 0.002(2) -0.006(2) -0.008(2) C26 0.057(4) 0.036(3) 0.044(4) -0.003(3) -0.011(3) -0.024(3) C27 0.101(6) 0.063(5) 0.082(6) -0.029(4) -0.022(5) -0.031(4) C28 0.056(4) 0.096(6) 0.073(5) -0.007(4) -0.021(4) -0.038(4) C29 0.041(3) 0.043(3) 0.030(3) 0.001(3) -0.011(2) -0.018(3) C30 0.048(4) 0.059(4) 0.061(4) 0.013(3) -0.021(3) -0.025(3) C31 0.059(4) 0.059(4) 0.050(4) -0.021(3) -0.001(3) -0.027(3) C32 0.029(3) 0.024(3) 0.027(3) -0.002(2) -0.001(2) -0.012(2) C33 0.030(3) 0.028(3) 0.024(3) -0.003(2) 0.001(2) -0.015(2) C34 0.033(3) 0.029(3) 0.028(3) -0.005(2) 0.000(2) -0.016(2) C35 0.027(3) 0.027(3) 0.031(3) -0.012(2) 0.004(2) -0.012(2) C36 0.034(3) 0.021(3) 0.025(3) -0.005(2) -0.002(2) -0.010(2) C37 0.029(3) 0.024(3) 0.026(3) -0.006(2) 0.003(2) -0.012(2) C38 0.026(3) 0.020(3) 0.025(3) -0.003(2) -0.002(2) -0.008(2) C39 0.027(3) 0.024(3) 0.023(3) -0.002(2) -0.002(2) -0.014(2) C40 0.032(3) 0.029(3) 0.032(3) 0.000(2) -0.007(2) -0.015(2) C41 0.040(3) 0.024(3) 0.040(3) -0.009(3) 0.000(3) -0.011(2) C42 0.047(3) 0.039(3) 0.031(3) -0.016(3) 0.001(3) -0.020(3) C43 0.043(3) 0.040(3) 0.032(3) -0.004(3) -0.008(3) -0.018(3) C44 0.038(3) 0.031(3) 0.033(3) -0.005(2) -0.006(2) -0.019(2) C45 0.034(3) 0.028(3) 0.038(3) -0.007(3) -0.005(2) -0.005(2) C46 0.042(3) 0.033(3) 0.030(3) -0.001(2) -0.011(2) -0.013(3) C47 0.042(3) 0.049(4) 0.054(4) 0.009(3) -0.010(3) -0.018(3) C48 0.049(4) 0.040(4) 0.065(4) 0.010(3) -0.014(3) -0.016(3) C49 0.082(5) 0.066(5) 0.090(6) 0.019(4) -0.052(5) -0.036(4) C50 0.061(4) 0.042(4) 0.049(4) 0.004(3) -0.011(3) -0.015(3) C51 0.032(3) 0.018(2) 0.023(3) 0.000(2) 0.002(2) -0.010(2) C52 0.034(3) 0.026(3) 0.031(3) 0.001(2) 0.000(2) -0.008(2) C53 0.029(3) 0.037(3) 0.043(3) -0.008(3) 0.004(3) -0.004(2) C54 0.049(4) 0.029(3) 0.036(3) -0.012(3) 0.003(3) -0.007(3) C55 0.050(4) 0.036(3) 0.027(3) -0.007(2) -0.001(3) -0.019(3) C56 0.032(3) 0.031(3) 0.028(3) -0.006(2) 0.004(2) -0.015(2) C57 0.034(3) 0.037(3) 0.051(4) -0.007(3) -0.010(3) -0.007(3) C58 0.049(4) 0.064(4) 0.069(5) 0.012(4) -0.023(3) -0.029(3) C59 0.057(4) 0.089(6) 0.060(5) 0.020(4) -0.028(4) -0.036(4) C60 0.035(3) 0.043(3) 0.032(3) -0.011(3) -0.007(2) -0.008(3) C61 0.048(4) 0.066(5) 0.082(5) -0.007(4) -0.012(4) -0.023(4) C62 0.059(4) 0.056(4) 0.047(4) 0.000(3) -0.020(3) -0.006(3) C63 0.047(4) 0.056(4) 0.045(4) -0.006(3) -0.005(3) -0.025(3) C64 0.049(4) 0.046(4) 0.062(4) -0.008(3) -0.010(3) -0.019(3) C65 0.053(4) 0.068(5) 0.071(5) 0.001(4) -0.014(4) -0.010(4) C66 0.064(4) 0.064(4) 0.047(4) 0.012(3) -0.018(3) -0.037(4) C67 0.067(5) 0.074(5) 0.089(6) -0.006(5) 0.003(4) -0.039(4) C68 0.083(5) 0.055(4) 0.064(5) -0.010(4) 0.027(4) -0.033(4) N1 0.030(2) 0.022(2) 0.022(2) -0.0014(18) -0.0013(18) -0.0102(19) N2 0.027(2) 0.022(2) 0.025(2) -0.0008(18) -0.0059(18) -0.0085(18) N3 0.027(2) 0.026(2) 0.021(2) -0.0045(18) -0.0004(17) -0.0110(18) N4 0.023(2) 0.022(2) 0.025(2) -0.0033(18) -0.0029(17) -0.0055(17) Cl1 0.0410(8) 0.0320(7) 0.0472(8) -0.0093(6) -0.0064(6) -0.0125(6) Cl2 0.0339(8) 0.0696(11) 0.0478(9) -0.0198(8) 0.0063(7) -0.0239(7) Cl3 0.0510(9) 0.0357(8) 0.0410(8) 0.0054(6) -0.0115(7) -0.0128(7) Cl4 0.0406(8) 0.0422(8) 0.0487(9) -0.0062(7) -0.0048(6) -0.0227(6) Cl5 0.204(3) 0.188(3) 0.105(2) 0.003(2) 0.005(2) -0.163(3) Cl6 0.0808(13) 0.0468(10) 0.0679(12) -0.0117(9) 0.0036(10) -0.0200(9) Cl7 0.128(2) 0.0781(16) 0.1008(19) 0.0302(14) 0.0083(16) -0.0161(15) Cl8 0.0445(9) 0.0680(11) 0.0535(10) 0.0017(8) -0.0024(7) -0.0210(8) Cl9 0.0848(16) 0.0826(16) 0.209(3) -0.0798(19) 0.0304(18) -0.0358(13) Cl10 0.0586(12) 0.1150(18) 0.0810(14) 0.0282(13) -0.0117(10) -0.0438(12) Cl11 0.0665(11) 0.0519(10) 0.0724(12) -0.0045(9) -0.0156(9) -0.0209(9) Cl12 0.0629(11) 0.0852(13) 0.0462(10) -0.0076(9) 0.0081(8) -0.0261(10) Cl13 0.0605(10) 0.0551(10) 0.0495(10) -0.0011(8) -0.0161(8) -0.0220(8) Cl14 0.0768(13) 0.0804(13) 0.0756(13) 0.0264(11) -0.0299(10) -0.0399(11) Cl15 0.0999(16) 0.0828(15) 0.0749(14) 0.0106(11) 0.0138(12) -0.0455(13) Cl16 0.0636(12) 0.0955(16) 0.0764(14) -0.0045(12) -0.0153(10) -0.0166(11) Cl17 0.0897(17) 0.0866(17) 0.161(3) -0.0204(17) -0.0159(16) -0.0427(14) Cl18 0.447(9) 0.173(4) 0.123(3) 0.087(3) -0.114(4) -0.142(5) Cl19 0.177(3) 0.128(3) 0.141(3) -0.023(2) 0.074(3) -0.065(2) Cl21 0.0902(16) 0.0974(17) 0.1126(19) 0.0195(14) -0.0317(14) -0.0514(14) Cl22 0.107(2) 0.175(3) 0.0985(19) -0.0141(19) -0.0319(16) -0.0692(19) Cl23 0.144(3) 0.318(5) 0.318(6) 0.264(5) -0.164(3) -0.169(4) Zn1 0.0273(3) 0.0269(3) 0.0268(3) -0.0042(3) -0.0005(2) -0.0069(2) Zn2 0.0353(3) 0.0263(3) 0.0292(3) 0.0001(3) -0.0015(3) -0.0148(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.277(6) . ? C1 C2 1.479(6) . ? C1 C5 1.532(7) . ? C2 C7 1.393(7) . ? C2 C3 1.415(7) . ? C3 C3 1.359(9) 2_765 ? C3 C4 1.409(7) . ? C4 C6 1.382(7) . ? C4 C5 1.488(6) . ? C5 N2 1.259(6) . ? C6 C7 1.430(6) 2_765 ? C6 H6 0.9300 . ? C7 C6 1.430(6) 2_765 ? C7 H7 0.9300 . ? C8 C13 1.402(7) . ? C8 C9 1.406(7) . ? C8 N1 1.440(6) . ? C9 C10 1.395(8) . ? C9 C14 1.524(7) . ? C10 C11 1.377(8) . ? C10 H10 0.9300 . ? C11 C12 1.372(8) . ? C11 H11 0.9300 . ? C12 C13 1.389(7) . ? C12 H12 0.9300 . ? C13 C17 1.506(7) . ? C14 C16 1.506(7) . ? C14 C15 1.522(8) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.511(8) . ? C17 C19 1.551(8) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C25 1.385(7) . ? C20 C21 1.408(7) . ? C20 N2 1.443(6) . ? C21 C22 1.398(8) . ? C21 C26 1.517(8) . ? C22 C23 1.393(8) . ? C22 H22 0.9300 . ? C23 C24 1.371(8) . ? C23 H23 0.9300 . ? C24 C25 1.390(8) . ? C24 H24 0.9300 . ? C25 C29 1.513(7) . ? C26 C27 1.534(9) . ? C26 C28 1.534(9) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.525(8) . ? C29 C31 1.542(7) . ? C29 H29 0.9800 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 N3 1.267(6) . ? C32 C33 1.480(7) . ? C32 C38 1.533(6) . ? C33 C34 1.379(6) . ? C33 C37 1.402(6) . ? C34 C35 1.436(7) . ? C34 H34 0.9300 . ? C35 C36 1.396(6) . ? C35 H35 0.9300 . ? C36 C37 1.418(6) 2_556 ? C36 C38 1.469(7) 2_556 ? C37 C37 1.364(9) 2_556 ? C37 C36 1.418(6) 2_556 ? C38 N4 1.273(6) . ? C38 C36 1.469(7) 2_556 ? C39 C40 1.393(7) . ? C39 C44 1.413(7) . ? C39 N4 1.445(6) . ? C40 C41 1.399(7) . ? C40 C45 1.521(8) . ? C41 C42 1.374(8) . ? C41 H41 0.9300 . ? C42 C43 1.391(8) . ? C42 H42 0.9300 . ? C43 C44 1.392(7) . ? C43 H43 0.9300 . ? C44 C46 1.517(7) . ? C45 C49 1.509(9) . ? C45 C50 1.515(8) . ? C45 H45 0.9800 . ? C46 C47 1.532(8) . ? C46 C48 1.533(8) . ? C46 H46 0.9800 . ? C47 H47A 0.9600 . ? C47 H47B 0.9600 . ? C47 H47C 0.9600 . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 0.9600 . ? C51 C56 1.388(7) . ? C51 C52 1.403(7) . ? C51 N3 1.449(6) . ? C52 C53 1.395(7) . ? C52 C57 1.523(8) . ? C53 C54 1.371(8) . ? C53 H53 0.9300 . ? C54 C55 1.375(8) . ? C54 H54 0.9300 . ? C55 C56 1.406(7) . ? C55 H55 0.9300 . ? C56 C60 1.512(7) . ? C57 C58 1.515(8) . ? C57 C59 1.524(9) . ? C57 H57 0.9800 . ? C58 H58A 0.9600 . ? C58 H58B 0.9600 . ? C58 H58C 0.9600 . ? C59 H59A 0.9600 . ? C59 H59B 0.9600 . ? C59 H59C 0.9600 . ? C60 C62 1.522(9) . ? C60 C61 1.534(8) . ? C60 H60 0.9800 . ? C61 H61A 0.9600 . ? C61 H61B 0.9600 . ? C61 H61C 0.9600 . ? C62 H62A 0.9600 . ? C62 H62B 0.9600 . ? C62 H62C 0.9600 . ? C63 Cl11 1.753(6) . ? C63 Cl12 1.758(6) . ? C63 Cl13 1.760(7) . ? C63 H63 0.9800 . ? C64 Cl10 1.741(7) . ? C64 Cl9 1.744(6) . ? C64 Cl8 1.760(6) . ? C64 H64 0.9800 . ? C65 Cl23 1.676(8) . ? C65 Cl22 1.717(8) . ? C65 Cl21 1.777(8) . ? C65 H65 0.9800 . ? C66 Cl14 1.738(7) . ? C66 Cl16 1.759(7) . ? C66 Cl15 1.766(7) . ? C66 H66 0.9800 . ? C67 Cl18 1.638(9) . ? C67 Cl19 1.706(8) . ? C67 Cl17 1.738(8) . ? C67 H67 0.9800 . ? C68 Cl7 1.722(9) . ? C68 Cl6 1.733(7) . ? C68 Cl5 1.786(9) . ? C68 H68 0.9800 . ? N1 Zn1 2.108(4) . ? N2 Zn1 2.147(4) . ? N3 Zn2 2.128(4) . ? N4 Zn2 2.121(4) . ? Cl1 Zn1 2.1950(15) . ? Cl2 Zn1 2.1734(17) . ? Cl3 Zn2 2.1874(17) . ? Cl4 Zn2 2.1878(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 133.8(5) . . ? N1 C1 C5 118.1(4) . . ? C2 C1 C5 107.7(4) . . ? C7 C2 C3 118.1(4) . . ? C7 C2 C1 137.9(5) . . ? C3 C2 C1 104.1(4) . . ? C3 C3 C4 121.5(6) 2_765 . ? C3 C3 C2 121.4(6) 2_765 . ? C4 C3 C2 117.1(4) . . ? C6 C4 C3 118.3(4) . . ? C6 C4 C5 137.3(4) . . ? C3 C4 C5 104.4(4) . . ? N2 C5 C4 134.4(5) . . ? N2 C5 C1 118.5(4) . . ? C4 C5 C1 106.7(4) . . ? C4 C6 C7 120.6(4) . 2_765 ? C4 C6 H6 119.7 . . ? C7 C6 H6 119.7 2_765 . ? C2 C7 C6 120.1(5) . 2_765 ? C2 C7 H7 120.0 . . ? C6 C7 H7 120.0 2_765 . ? C13 C8 C9 123.1(5) . . ? C13 C8 N1 120.3(4) . . ? C9 C8 N1 116.6(4) . . ? C10 C9 C8 116.9(5) . . ? C10 C9 C14 120.4(5) . . ? C8 C9 C14 122.8(5) . . ? C11 C10 C9 121.0(5) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 120.4(5) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 122.0(5) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C12 C13 C8 116.5(5) . . ? C12 C13 C17 121.4(5) . . ? C8 C13 C17 122.1(5) . . ? C16 C14 C15 110.1(5) . . ? C16 C14 C9 112.3(5) . . ? C15 C14 C9 112.6(5) . . ? C16 C14 H14 107.2 . . ? C15 C14 H14 107.2 . . ? C9 C14 H14 107.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 C18 112.4(5) . . ? C13 C17 C19 110.8(5) . . ? C18 C17 C19 109.0(5) . . ? C13 C17 H17 108.2 . . ? C18 C17 H17 108.2 . . ? C19 C17 H17 108.2 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 123.0(5) . . ? C25 C20 N2 119.6(4) . . ? C21 C20 N2 117.3(4) . . ? C22 C21 C20 116.6(5) . . ? C22 C21 C26 119.6(5) . . ? C20 C21 C26 123.7(5) . . ? C23 C22 C21 121.3(5) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C24 C23 C22 119.6(5) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C23 C24 C25 121.7(5) . . ? C23 C24 H24 119.2 . . ? C25 C24 H24 119.2 . . ? C20 C25 C24 117.6(5) . . ? C20 C25 C29 122.0(5) . . ? C24 C25 C29 120.3(5) . . ? C21 C26 C27 112.9(5) . . ? C21 C26 C28 110.6(5) . . ? C27 C26 C28 110.2(6) . . ? C21 C26 H26 107.6 . . ? C27 C26 H26 107.6 . . ? C28 C26 H26 107.6 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 C30 112.5(5) . . ? C25 C29 C31 111.7(5) . . ? C30 C29 C31 110.2(5) . . ? C25 C29 H29 107.4 . . ? C30 C29 H29 107.4 . . ? C31 C29 H29 107.4 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N3 C32 C33 134.4(4) . . ? N3 C32 C38 118.4(4) . . ? C33 C32 C38 106.9(4) . . ? C34 C33 C37 118.5(4) . . ? C34 C33 C32 137.1(4) . . ? C37 C33 C32 104.3(4) . . ? C33 C34 C35 120.0(4) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C36 C35 C34 120.6(4) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C37 118.0(4) . 2_556 ? C35 C36 C38 137.9(4) . 2_556 ? C37 C36 C38 104.1(4) 2_556 2_556 ? C37 C37 C33 122.4(5) 2_556 . ? C37 C37 C36 120.5(5) 2_556 2_556 ? C33 C37 C36 117.1(4) . 2_556 ? N4 C38 C36 133.7(4) . 2_556 ? N4 C38 C32 118.7(4) . . ? C36 C38 C32 107.5(4) 2_556 . ? C40 C39 C44 124.1(4) . . ? C40 C39 N4 118.4(4) . . ? C44 C39 N4 117.5(4) . . ? C39 C40 C41 117.0(5) . . ? C39 C40 C45 120.9(4) . . ? C41 C40 C45 122.0(5) . . ? C42 C41 C40 120.9(5) . . ? C42 C41 H41 119.6 . . ? C40 C41 H41 119.6 . . ? C41 C42 C43 120.6(5) . . ? C41 C42 H42 119.7 . . ? C43 C42 H42 119.7 . . ? C42 C43 C44 121.7(5) . . ? C42 C43 H43 119.2 . . ? C44 C43 H43 119.2 . . ? C43 C44 C39 115.7(5) . . ? C43 C44 C46 119.5(5) . . ? C39 C44 C46 124.7(4) . . ? C49 C45 C50 111.2(5) . . ? C49 C45 C40 110.7(5) . . ? C50 C45 C40 113.0(5) . . ? C49 C45 H45 107.2 . . ? C50 C45 H45 107.2 . . ? C40 C45 H45 107.2 . . ? C44 C46 C47 110.7(4) . . ? C44 C46 C48 112.6(5) . . ? C47 C46 C48 110.5(5) . . ? C44 C46 H46 107.6 . . ? C47 C46 H46 107.6 . . ? C48 C46 H46 107.6 . . ? C46 C47 H47A 109.5 . . ? C46 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C46 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C46 C48 H48A 109.5 . . ? C46 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C46 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C45 C49 H49A 109.5 . . ? C45 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C45 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C45 C50 H50A 109.5 . . ? C45 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C45 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C56 C51 C52 123.2(4) . . ? C56 C51 N3 120.0(4) . . ? C52 C51 N3 116.8(4) . . ? C53 C52 C51 117.3(5) . . ? C53 C52 C57 120.7(5) . . ? C51 C52 C57 122.0(4) . . ? C54 C53 C52 120.6(5) . . ? C54 C53 H53 119.7 . . ? C52 C53 H53 119.7 . . ? C53 C54 C55 121.1(5) . . ? C53 C54 H54 119.4 . . ? C55 C54 H54 119.4 . . ? C54 C55 C56 120.9(5) . . ? C54 C55 H55 119.6 . . ? C56 C55 H55 119.6 . . ? C51 C56 C55 116.7(5) . . ? C51 C56 C60 123.9(4) . . ? C55 C56 C60 119.3(5) . . ? C58 C57 C52 113.8(5) . . ? C58 C57 C59 110.2(5) . . ? C52 C57 C59 111.7(5) . . ? C58 C57 H57 106.9 . . ? C52 C57 H57 106.9 . . ? C59 C57 H57 106.9 . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C57 C59 H59A 109.5 . . ? C57 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C57 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C56 C60 C62 111.9(5) . . ? C56 C60 C61 111.8(5) . . ? C62 C60 C61 110.8(5) . . ? C56 C60 H60 107.4 . . ? C62 C60 H60 107.4 . . ? C61 C60 H60 107.4 . . ? C60 C61 H61A 109.5 . . ? C60 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? C60 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? C60 C62 H62A 109.5 . . ? C60 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C60 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? Cl11 C63 Cl12 110.3(3) . . ? Cl11 C63 Cl13 110.8(3) . . ? Cl12 C63 Cl13 109.9(3) . . ? Cl11 C63 H63 108.6 . . ? Cl12 C63 H63 108.6 . . ? Cl13 C63 H63 108.6 . . ? Cl10 C64 Cl9 111.7(4) . . ? Cl10 C64 Cl8 110.9(4) . . ? Cl9 C64 Cl8 109.8(3) . . ? Cl10 C64 H64 108.1 . . ? Cl9 C64 H64 108.1 . . ? Cl8 C64 H64 108.1 . . ? Cl23 C65 Cl22 113.9(5) . . ? Cl23 C65 Cl21 109.1(4) . . ? Cl22 C65 Cl21 110.0(4) . . ? Cl23 C65 H65 107.9 . . ? Cl22 C65 H65 107.9 . . ? Cl21 C65 H65 107.9 . . ? Cl14 C66 Cl16 110.4(4) . . ? Cl14 C66 Cl15 110.1(4) . . ? Cl16 C66 Cl15 109.4(4) . . ? Cl14 C66 H66 109.0 . . ? Cl16 C66 H66 109.0 . . ? Cl15 C66 H66 109.0 . . ? Cl18 C67 Cl19 112.6(5) . . ? Cl18 C67 Cl17 112.3(5) . . ? Cl19 C67 Cl17 110.4(4) . . ? Cl18 C67 H67 107.1 . . ? Cl19 C67 H67 107.1 . . ? Cl17 C67 H67 107.1 . . ? Cl7 C68 Cl6 112.4(5) . . ? Cl7 C68 Cl5 110.6(4) . . ? Cl6 C68 Cl5 109.0(4) . . ? Cl7 C68 H68 108.2 . . ? Cl6 C68 H68 108.2 . . ? Cl5 C68 H68 108.2 . . ? C1 N1 C8 120.1(4) . . ? C1 N1 Zn1 111.2(3) . . ? C8 N1 Zn1 128.6(3) . . ? C5 N2 C20 121.0(4) . . ? C5 N2 Zn1 110.4(3) . . ? C20 N2 Zn1 128.5(3) . . ? C32 N3 C51 120.3(4) . . ? C32 N3 Zn2 111.1(3) . . ? C51 N3 Zn2 128.6(3) . . ? C38 N4 C39 119.1(4) . . ? C38 N4 Zn2 110.9(3) . . ? C39 N4 Zn2 129.7(3) . . ? N1 Zn1 N2 79.99(15) . . ? N1 Zn1 Cl2 112.02(12) . . ? N2 Zn1 Cl2 115.64(12) . . ? N1 Zn1 Cl1 111.33(11) . . ? N2 Zn1 Cl1 110.65(11) . . ? Cl2 Zn1 Cl1 120.26(6) . . ? N4 Zn2 N3 80.55(14) . . ? N4 Zn2 Cl3 115.24(12) . . ? N3 Zn2 Cl3 108.17(12) . . ? N4 Zn2 Cl4 109.09(12) . . ? N3 Zn2 Cl4 115.69(12) . . ? Cl3 Zn2 Cl4 121.18(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 N1 C1 C2 C7 5.8(10) . . . . ? C5 C1 C2 C7 178.2(6) . . . . ? N1 C1 C2 C3 -173.7(5) . . . . ? C5 C1 C2 C3 -1.3(5) . . . . ? C7 C2 C3 C3 1.2(9) . . . 2_765 ? C1 C2 C3 C3 -179.2(6) . . . 2_765 ? C7 C2 C3 C4 -178.6(4) . . . . ? C1 C2 C3 C4 1.0(6) . . . . ? C3 C3 C4 C6 1.2(9) 2_765 . . . ? C2 C3 C4 C6 -179.1(4) . . . . ? C3 C3 C4 C5 179.9(6) 2_765 . . . ? C2 C3 C4 C5 -0.3(6) . . . . ? C6 C4 C5 N2 -9.5(10) . . . . ? C3 C4 C5 N2 172.1(5) . . . . ? C6 C4 C5 C1 177.9(6) . . . . ? C3 C4 C5 C1 -0.5(5) . . . . ? N1 C1 C5 N2 0.9(7) . . . . ? C2 C1 C5 N2 -172.9(4) . . . . ? N1 C1 C5 C4 174.9(4) . . . . ? C2 C1 C5 C4 1.1(5) . . . . ? C3 C4 C6 C7 -0.7(7) . . . 2_765 ? C5 C4 C6 C7 -178.9(5) . . . 2_765 ? C3 C2 C7 C6 -1.7(7) . . . 2_765 ? C1 C2 C7 C6 178.9(5) . . . 2_765 ? C13 C8 C9 C10 4.7(7) . . . . ? N1 C8 C9 C10 -178.2(4) . . . . ? C13 C8 C9 C14 -175.2(4) . . . . ? N1 C8 C9 C14 1.8(6) . . . . ? C8 C9 C10 C11 -1.9(7) . . . . ? C14 C9 C10 C11 178.0(5) . . . . ? C9 C10 C11 C12 -2.3(8) . . . . ? C10 C11 C12 C13 4.0(8) . . . . ? C11 C12 C13 C8 -1.4(7) . . . . ? C11 C12 C13 C17 179.3(5) . . . . ? C9 C8 C13 C12 -3.1(7) . . . . ? N1 C8 C13 C12 179.9(4) . . . . ? C9 C8 C13 C17 176.2(4) . . . . ? N1 C8 C13 C17 -0.8(6) . . . . ? C10 C9 C14 C16 78.1(6) . . . . ? C8 C9 C14 C16 -101.9(6) . . . . ? C10 C9 C14 C15 -46.8(7) . . . . ? C8 C9 C14 C15 133.2(5) . . . . ? C12 C13 C17 C18 -61.2(7) . . . . ? C8 C13 C17 C18 119.6(5) . . . . ? C12 C13 C17 C19 61.0(6) . . . . ? C8 C13 C17 C19 -118.3(5) . . . . ? C25 C20 C21 C22 1.1(7) . . . . ? N2 C20 C21 C22 -176.1(4) . . . . ? C25 C20 C21 C26 178.6(5) . . . . ? N2 C20 C21 C26 1.4(7) . . . . ? C20 C21 C22 C23 -2.2(7) . . . . ? C26 C21 C22 C23 -179.8(5) . . . . ? C21 C22 C23 C24 1.6(8) . . . . ? C22 C23 C24 C25 0.2(8) . . . . ? C21 C20 C25 C24 0.7(7) . . . . ? N2 C20 C25 C24 177.7(4) . . . . ? C21 C20 C25 C29 177.9(4) . . . . ? N2 C20 C25 C29 -5.0(7) . . . . ? C23 C24 C25 C20 -1.3(8) . . . . ? C23 C24 C25 C29 -178.6(5) . . . . ? C22 C21 C26 C27 -49.3(7) . . . . ? C20 C21 C26 C27 133.3(6) . . . . ? C22 C21 C26 C28 74.7(7) . . . . ? C20 C21 C26 C28 -102.7(6) . . . . ? C20 C25 C29 C30 -106.1(6) . . . . ? C24 C25 C29 C30 71.0(6) . . . . ? C20 C25 C29 C31 129.3(5) . . . . ? C24 C25 C29 C31 -53.6(7) . . . . ? N3 C32 C33 C34 -1.7(11) . . . . ? C38 C32 C33 C34 -175.3(6) . . . . ? N3 C32 C33 C37 174.4(6) . . . . ? C38 C32 C33 C37 0.8(5) . . . . ? C37 C33 C34 C35 2.8(7) . . . . ? C32 C33 C34 C35 178.5(6) . . . . ? C33 C34 C35 C36 -0.8(8) . . . . ? C34 C35 C36 C37 -1.1(7) . . . 2_556 ? C34 C35 C36 C38 178.2(6) . . . 2_556 ? C34 C33 C37 C37 -2.9(9) . . . 2_556 ? C32 C33 C37 C37 -179.9(6) . . . 2_556 ? C34 C33 C37 C36 178.0(5) . . . 2_556 ? C32 C33 C37 C36 1.0(6) . . . 2_556 ? N3 C32 C38 N4 -1.2(7) . . . . ? C33 C32 C38 N4 173.7(4) . . . . ? N3 C32 C38 C36 -177.1(5) . . . 2_556 ? C33 C32 C38 C36 -2.2(5) . . . 2_556 ? C44 C39 C40 C41 -1.8(7) . . . . ? N4 C39 C40 C41 -179.8(4) . . . . ? C44 C39 C40 C45 -178.7(5) . . . . ? N4 C39 C40 C45 3.3(7) . . . . ? C39 C40 C41 C42 0.7(8) . . . . ? C45 C40 C41 C42 177.6(5) . . . . ? C40 C41 C42 C43 0.8(8) . . . . ? C41 C42 C43 C44 -1.4(9) . . . . ? C42 C43 C44 C39 0.3(8) . . . . ? C42 C43 C44 C46 177.3(5) . . . . ? C40 C39 C44 C43 1.3(7) . . . . ? N4 C39 C44 C43 179.3(4) . . . . ? C40 C39 C44 C46 -175.5(5) . . . . ? N4 C39 C44 C46 2.5(7) . . . . ? C39 C40 C45 C49 87.3(6) . . . . ? C41 C40 C45 C49 -89.5(6) . . . . ? C39 C40 C45 C50 -147.3(5) . . . . ? C41 C40 C45 C50 36.0(7) . . . . ? C43 C44 C46 C47 -71.1(6) . . . . ? C39 C44 C46 C47 105.5(6) . . . . ? C43 C44 C46 C48 53.1(7) . . . . ? C39 C44 C46 C48 -130.3(5) . . . . ? C56 C51 C52 C53 -3.9(8) . . . . ? N3 C51 C52 C53 177.7(5) . . . . ? C56 C51 C52 C57 177.3(5) . . . . ? N3 C51 C52 C57 -1.1(7) . . . . ? C51 C52 C53 C54 0.5(8) . . . . ? C57 C52 C53 C54 179.3(5) . . . . ? C52 C53 C54 C55 1.5(9) . . . . ? C53 C54 C55 C56 -0.3(9) . . . . ? C52 C51 C56 C55 5.0(7) . . . . ? N3 C51 C56 C55 -176.6(4) . . . . ? C52 C51 C56 C60 -171.0(5) . . . . ? N3 C51 C56 C60 7.3(7) . . . . ? C54 C55 C56 C51 -2.9(8) . . . . ? C54 C55 C56 C60 173.4(5) . . . . ? C53 C52 C57 C58 41.9(7) . . . . ? C51 C52 C57 C58 -139.3(5) . . . . ? C53 C52 C57 C59 -83.8(7) . . . . ? C51 C52 C57 C59 95.0(6) . . . . ? C51 C56 C60 C62 116.6(6) . . . . ? C55 C56 C60 C62 -59.3(7) . . . . ? C51 C56 C60 C61 -118.4(6) . . . . ? C55 C56 C60 C61 65.6(7) . . . . ? C2 C1 N1 C8 4.1(8) . . . . ? C5 C1 N1 C8 -167.7(4) . . . . ? C2 C1 N1 Zn1 -179.0(5) . . . . ? C5 C1 N1 Zn1 9.2(5) . . . . ? C13 C8 N1 C1 -93.5(5) . . . . ? C9 C8 N1 C1 89.4(5) . . . . ? C13 C8 N1 Zn1 90.3(5) . . . . ? C9 C8 N1 Zn1 -86.8(5) . . . . ? C4 C5 N2 C20 -6.6(8) . . . . ? C1 C5 N2 C20 165.4(4) . . . . ? C4 C5 N2 Zn1 177.8(4) . . . . ? C1 C5 N2 Zn1 -10.2(5) . . . . ? C25 C20 N2 C5 109.4(5) . . . . ? C21 C20 N2 C5 -73.3(6) . . . . ? C25 C20 N2 Zn1 -75.8(5) . . . . ? C21 C20 N2 Zn1 101.4(4) . . . . ? C33 C32 N3 C51 4.3(9) . . . . ? C38 C32 N3 C51 177.4(4) . . . . ? C33 C32 N3 Zn2 -177.0(5) . . . . ? C38 C32 N3 Zn2 -3.9(6) . . . . ? C56 C51 N3 C32 83.5(6) . . . . ? C52 C51 N3 C32 -98.1(6) . . . . ? C56 C51 N3 Zn2 -95.0(5) . . . . ? C52 C51 N3 Zn2 83.4(5) . . . . ? C36 C38 N4 C39 6.6(8) 2_556 . . . ? C32 C38 N4 C39 -168.0(4) . . . . ? C36 C38 N4 Zn2 -179.9(5) 2_556 . . . ? C32 C38 N4 Zn2 5.5(5) . . . . ? C40 C39 N4 C38 -112.9(5) . . . . ? C44 C39 N4 C38 68.9(6) . . . . ? C40 C39 N4 Zn2 75.0(5) . . . . ? C44 C39 N4 Zn2 -103.2(5) . . . . ? C1 N1 Zn1 N2 -10.9(3) . . . . ? C8 N1 Zn1 N2 165.6(4) . . . . ? C1 N1 Zn1 Cl2 -124.7(3) . . . . ? C8 N1 Zn1 Cl2 51.8(4) . . . . ? C1 N1 Zn1 Cl1 97.5(3) . . . . ? C8 N1 Zn1 Cl1 -86.0(4) . . . . ? C5 N2 Zn1 N1 11.4(3) . . . . ? C20 N2 Zn1 N1 -163.8(4) . . . . ? C5 N2 Zn1 Cl2 121.1(3) . . . . ? C20 N2 Zn1 Cl2 -54.1(4) . . . . ? C5 N2 Zn1 Cl1 -97.8(3) . . . . ? C20 N2 Zn1 Cl1 87.1(4) . . . . ? C38 N4 Zn2 N3 -5.7(3) . . . . ? C39 N4 Zn2 N3 166.9(4) . . . . ? C38 N4 Zn2 Cl3 100.0(3) . . . . ? C39 N4 Zn2 Cl3 -87.4(4) . . . . ? C38 N4 Zn2 Cl4 -119.7(3) . . . . ? C39 N4 Zn2 Cl4 52.9(4) . . . . ? C32 N3 Zn2 N4 5.1(4) . . . . ? C51 N3 Zn2 N4 -176.3(4) . . . . ? C32 N3 Zn2 Cl3 -108.5(3) . . . . ? C51 N3 Zn2 Cl3 70.1(4) . . . . ? C32 N3 Zn2 Cl4 111.8(3) . . . . ? C51 N3 Zn2 Cl4 -69.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.031 _refine_diff_density_min -1.817 _refine_diff_density_rms 0.108 # Attachment 'Compound 5.cif' data_ccdkvkv059a _database_code_depnum_ccdc_archive 'CCDC 670791' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _publ_section_synopsis ; ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Sluis, P. v.d. & Spek, A. L. (1990). SQUEEZE. Acta Cryst. A46, 194-201. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H36 Br Cu N2, C4 H8 O' _chemical_formula_sum 'C35 H44 Br Cu N2 O' _chemical_formula_weight 652.17 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p21/c _symmetry_space_group_name_Hall -p2ybc 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 13.719(3) _cell_length_b 13.400(3) _cell_length_c 19.628(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.77(3) _cell_angle_gamma 90.00 _cell_volume 3454.9(12) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Black-Green _exptl_crystal_size_max .15 _exptl_crystal_size_mid .10 _exptl_crystal_size_min .10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 1.816 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22151 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.0928 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.41 _reflns_number_total 7850 _reflns_number_gt 4596 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.1349P)^2^+3.2961P] 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 7850 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1318 _refine_ls_R_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.2403 _refine_ls_wR_factor_gt 0.2037 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 C6 C -0.4306(4) 0.6569(4) 0.0647(3) 0.0250(12) Uani 1 1 d . . . H6 H -0.3905 0.7100 0.0874 0.030 Uiso 1 1 calc R . . C7 C -0.4648(4) 0.3448(4) -0.0600(3) 0.0272(12) Uani 1 1 d . . . H7 H -0.4363 0.2924 -0.0788 0.033 Uiso 1 1 calc R . . C32 C -0.4870(6) 0.6105(9) -0.1711(5) 0.087(3) Uani 1 1 d . . . H32A H -0.5176 0.6683 -0.1558 0.105 Uiso 1 1 calc R . . H32B H -0.5199 0.5509 -0.1603 0.105 Uiso 1 1 calc R . . C33 C -0.4981(6) 0.6162(8) -0.2474(5) 0.076(3) Uani 1 1 d . . . H33A H -0.5598 0.6515 -0.2725 0.092 Uiso 1 1 calc R . . H33B H -0.4990 0.5502 -0.2679 0.092 Uiso 1 1 calc R . . C34 C -0.4040(7) 0.6740(10) -0.2495(6) 0.107(4) Uani 1 1 d . . . H34A H -0.3795 0.6517 -0.2886 0.128 Uiso 1 1 calc R . . H34B H -0.4180 0.7450 -0.2545 0.128 Uiso 1 1 calc R . . C35 C -0.3301(6) 0.6516(7) -0.1809(5) 0.068(2) Uani 1 1 d . . . H35A H -0.2784 0.6066 -0.1877 0.081 Uiso 1 1 calc R . . H35B H -0.2969 0.7126 -0.1594 0.081 Uiso 1 1 calc R . . N1 N -0.1947(3) 0.5902(3) 0.0542(2) 0.0239(10) Uani 1 1 d . . . N2 N -0.2150(3) 0.4128(3) -0.0163(2) 0.0225(10) Uani 1 1 d . . . O1 O -0.3809(4) 0.6076(5) -0.1363(3) 0.0776(18) Uani 1 1 d . . . C1 C -0.2837(4) 0.5534(4) 0.0290(3) 0.0238(12) Uani 1 1 d . . . C2 C -0.3864(4) 0.5799(4) 0.0357(3) 0.0224(11) Uani 1 1 d . . . C3 C -0.4497(4) 0.5015(4) 0.0022(3) 0.0224(12) Uani 1 1 d . . . C4 C -0.4039(4) 0.4247(4) -0.0274(3) 0.0232(12) Uani 1 1 d . . . C5 C -0.2949(4) 0.4556(4) -0.0101(3) 0.0239(12) Uani 1 1 d . . . C8 C -0.1782(4) 0.6713(4) 0.1045(3) 0.0258(12) Uani 1 1 d . . . C9 C -0.1608(4) 0.7680(5) 0.0816(3) 0.0326(14) Uani 1 1 d . . . C10 C -0.1415(5) 0.8435(5) 0.1317(4) 0.0462(17) Uani 1 1 d . . . H10 H -0.1309 0.9080 0.1179 0.055 Uiso 1 1 calc R . . C11 C -0.1376(5) 0.8258(5) 0.2021(4) 0.0452(17) Uani 1 1 d . . . H11 H -0.1239 0.8778 0.2349 0.054 Uiso 1 1 calc R . . C12 C -0.1539(5) 0.7310(5) 0.2231(3) 0.0406(16) Uani 1 1 d . . . H12 H -0.1505 0.7194 0.2704 0.049 Uiso 1 1 calc R . . C13 C -0.1756(4) 0.6516(4) 0.1748(3) 0.0289(13) Uani 1 1 d . . . C14 C -0.1690(5) 0.7895(5) 0.0038(4) 0.0451(17) Uani 1 1 d . . . H14 H -0.1674 0.7253 -0.0197 0.054 Uiso 1 1 calc R . . C15 C -0.2699(6) 0.8388(6) -0.0331(4) 0.059(2) Uani 1 1 d . . . H15A H -0.2781 0.8973 -0.0070 0.088 Uiso 1 1 calc R . . H15B H -0.3244 0.7930 -0.0351 0.088 Uiso 1 1 calc R . . H15C H -0.2710 0.8575 -0.0805 0.088 Uiso 1 1 calc R . . C16 C -0.0788(6) 0.8507(6) -0.0033(5) 0.065(2) Uani 1 1 d . . . H16A H -0.0837 0.9175 0.0131 0.098 Uiso 1 1 calc R . . H16B H -0.0793 0.8524 -0.0523 0.098 Uiso 1 1 calc R . . H16C H -0.0167 0.8207 0.0248 0.098 Uiso 1 1 calc R . . C17 C -0.1937(5) 0.5472(5) 0.2001(3) 0.0383(15) Uani 1 1 d . . . H17 H -0.2242 0.5062 0.1580 0.046 Uiso 1 1 calc R . . C18 C -0.2650(6) 0.5481(6) 0.2450(4) 0.059(2) Uani 1 1 d . . . H18A H -0.2330 0.5808 0.2894 0.088 Uiso 1 1 calc R . . H18B H -0.2819 0.4808 0.2540 0.088 Uiso 1 1 calc R . . H18C H -0.3260 0.5834 0.2205 0.088 Uiso 1 1 calc R . . C19 C -0.0909(5) 0.5001(6) 0.2404(5) 0.061(2) Uani 1 1 d . . . H19A H -0.0489 0.4945 0.2090 0.092 Uiso 1 1 calc R . . H19B H -0.1023 0.4349 0.2570 0.092 Uiso 1 1 calc R . . H19C H -0.0575 0.5414 0.2803 0.092 Uiso 1 1 calc R . . C20 C -0.2193(4) 0.3115(4) -0.0399(3) 0.0249(12) Uani 1 1 d . . . C21 C -0.2029(4) 0.2365(5) 0.0114(3) 0.0319(13) Uani 1 1 d . . . C22 C -0.2082(5) 0.1386(5) -0.0125(4) 0.0437(16) Uani 1 1 d . . . H22 H -0.2006 0.0870 0.0203 0.052 Uiso 1 1 calc R . . C23 C -0.2244(5) 0.1157(5) -0.0833(4) 0.0453(17) Uani 1 1 d . . . H23 H -0.2288 0.0494 -0.0979 0.054 Uiso 1 1 calc R . . C24 C -0.2341(5) 0.1916(5) -0.1325(3) 0.0400(15) Uani 1 1 d . . . H24 H -0.2421 0.1758 -0.1800 0.048 Uiso 1 1 calc R . . C25 C -0.2322(4) 0.2915(5) -0.1122(3) 0.0312(13) Uani 1 1 d . . . C26 C -0.2401(5) 0.3728(5) -0.1662(3) 0.0447(17) Uani 1 1 d . . . H26 H -0.2353 0.4372 -0.1418 0.054 Uiso 1 1 calc R . . C27 C -0.1493(7) 0.3644(7) -0.1977(4) 0.067(2) Uani 1 1 d . . . H27A H -0.0874 0.3811 -0.1618 0.101 Uiso 1 1 calc R . . H27B H -0.1591 0.4096 -0.2371 0.101 Uiso 1 1 calc R . . H27C H -0.1449 0.2974 -0.2138 0.101 Uiso 1 1 calc R . . C28 C -0.3420(7) 0.3692(6) -0.2243(4) 0.065(2) Uani 1 1 d . . . H28A H -0.3489 0.3060 -0.2483 0.097 Uiso 1 1 calc R . . H28B H -0.3447 0.4219 -0.2579 0.097 Uiso 1 1 calc R . . H28C H -0.3965 0.3773 -0.2031 0.097 Uiso 1 1 calc R . . C29 C -0.1772(4) 0.2620(5) 0.0903(3) 0.0380(15) Uani 1 1 d . . . H29 H -0.1499 0.3300 0.0961 0.046 Uiso 1 1 calc R . . C30 C -0.2721(5) 0.2617(6) 0.1168(3) 0.0465(17) Uani 1 1 d . . . H30A H -0.3246 0.3009 0.0853 0.070 Uiso 1 1 calc R . . H30B H -0.2553 0.2896 0.1638 0.070 Uiso 1 1 calc R . . H30C H -0.2956 0.1944 0.1179 0.070 Uiso 1 1 calc R . . C31 C -0.0957(5) 0.1944(6) 0.1359(3) 0.0472(18) Uani 1 1 d . . . H31A H -0.1234 0.1289 0.1374 0.071 Uiso 1 1 calc R . . H31B H -0.0725 0.2209 0.1833 0.071 Uiso 1 1 calc R . . H31C H -0.0395 0.1906 0.1161 0.071 Uiso 1 1 calc R . . Cu1 Cu -0.08894(5) 0.51050(6) 0.01669(4) 0.0324(2) Uani 1 1 d . . . Br1 Br 0.05311(4) 0.41369(5) 0.08670(3) 0.0333(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C6 0.024(3) 0.023(3) 0.029(3) -0.003(2) 0.010(2) -0.004(2) C7 0.027(3) 0.024(3) 0.031(3) -0.004(2) 0.009(2) 0.004(2) C32 0.049(5) 0.131(9) 0.085(7) 0.040(7) 0.024(5) 0.012(5) C33 0.041(4) 0.092(7) 0.085(7) 0.029(6) 0.000(4) 0.003(4) C34 0.061(6) 0.149(11) 0.100(8) 0.062(8) 0.007(5) -0.011(6) C35 0.057(5) 0.072(6) 0.068(6) 0.011(5) 0.007(4) -0.012(4) N1 0.021(2) 0.026(3) 0.026(2) -0.001(2) 0.0086(18) 0.0009(18) N2 0.018(2) 0.028(3) 0.023(2) -0.001(2) 0.0097(17) 0.0003(18) O1 0.058(3) 0.111(5) 0.062(4) 0.027(4) 0.014(3) 0.000(3) C1 0.023(3) 0.025(3) 0.023(3) 0.004(2) 0.008(2) -0.001(2) C2 0.020(2) 0.022(3) 0.026(3) -0.002(2) 0.008(2) -0.001(2) C3 0.025(3) 0.023(3) 0.020(3) -0.003(2) 0.009(2) 0.001(2) C4 0.022(3) 0.027(3) 0.021(3) -0.001(2) 0.007(2) 0.001(2) C5 0.024(3) 0.026(3) 0.020(3) 0.002(2) 0.006(2) 0.000(2) C8 0.018(2) 0.028(3) 0.031(3) -0.004(3) 0.008(2) -0.001(2) C9 0.034(3) 0.028(3) 0.038(4) -0.003(3) 0.015(3) -0.002(2) C10 0.051(4) 0.026(4) 0.066(5) -0.008(3) 0.025(3) -0.007(3) C11 0.051(4) 0.034(4) 0.052(4) -0.020(3) 0.017(3) -0.014(3) C12 0.036(3) 0.052(5) 0.034(4) -0.010(3) 0.010(3) -0.004(3) C13 0.026(3) 0.031(3) 0.028(3) 0.002(3) 0.004(2) -0.001(2) C14 0.060(4) 0.027(4) 0.059(5) 0.006(3) 0.033(4) 0.001(3) C15 0.064(5) 0.055(5) 0.058(5) 0.010(4) 0.018(4) -0.002(4) C16 0.069(5) 0.053(5) 0.094(6) 0.013(5) 0.055(5) 0.003(4) C17 0.041(3) 0.039(4) 0.033(4) 0.004(3) 0.008(3) 0.000(3) C18 0.057(5) 0.054(5) 0.076(6) 0.026(4) 0.037(4) 0.007(4) C19 0.046(4) 0.051(5) 0.087(6) 0.015(4) 0.018(4) 0.016(3) C20 0.020(2) 0.023(3) 0.033(3) -0.004(2) 0.010(2) 0.002(2) C21 0.032(3) 0.032(4) 0.033(3) 0.000(3) 0.012(2) 0.002(2) C22 0.050(4) 0.029(4) 0.054(4) 0.009(3) 0.019(3) 0.004(3) C23 0.063(4) 0.031(4) 0.043(4) -0.007(3) 0.017(3) 0.004(3) C24 0.052(4) 0.033(4) 0.037(4) -0.012(3) 0.016(3) -0.002(3) C25 0.030(3) 0.034(4) 0.031(3) -0.002(3) 0.012(2) 0.003(3) C26 0.064(4) 0.043(4) 0.028(4) -0.007(3) 0.016(3) -0.006(3) C27 0.097(6) 0.065(6) 0.056(5) -0.015(4) 0.048(5) -0.034(5) C28 0.094(6) 0.058(5) 0.035(4) 0.005(4) 0.007(4) 0.016(5) C29 0.038(3) 0.040(4) 0.036(4) 0.009(3) 0.010(3) 0.002(3) C30 0.045(4) 0.060(5) 0.036(4) 0.008(3) 0.015(3) 0.010(3) C31 0.038(4) 0.068(5) 0.037(4) 0.015(4) 0.014(3) 0.006(3) Cu1 0.0214(4) 0.0389(5) 0.0394(5) 0.0018(3) 0.0124(3) -0.0001(3) Br1 0.0250(3) 0.0404(4) 0.0359(4) 0.0053(3) 0.0112(2) 0.0024(2) _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 C6 C2 1.399(8) . ? C6 C7 1.412(7) 3_465 ? C6 H6 0.9300 . ? C7 C4 1.394(8) . ? C7 C6 1.412(7) 3_465 ? C7 H7 0.9300 . ? C32 O1 1.419(9) . ? C32 C33 1.463(13) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.516(13) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.464(12) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 O1 1.397(10) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? N1 C1 1.276(7) . ? N1 C8 1.441(7) . ? N1 Cu1 2.099(4) . ? N2 C5 1.274(7) . ? N2 C20 1.430(7) . ? N2 Cu1 2.116(4) . ? C1 C2 1.495(7) . ? C1 C5 1.504(8) . ? C2 C3 1.401(7) . ? C3 C3 1.358(10) 3_465 ? C3 C4 1.416(8) . ? C4 C5 1.493(7) . ? C8 C13 1.396(8) . ? C8 C9 1.415(8) . ? C9 C10 1.383(9) . ? C9 C14 1.526(9) . ? C10 C11 1.387(10) . ? C10 H10 0.9300 . ? C11 C12 1.373(10) . ? C11 H11 0.9300 . ? C12 C13 1.398(9) . ? C12 H12 0.9300 . ? C13 C17 1.529(9) . ? C14 C15 1.515(10) . ? C14 C16 1.523(10) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.494(9) . ? C17 C19 1.538(9) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.395(8) . ? C20 C25 1.405(8) . ? C21 C22 1.388(9) . ? C21 C29 1.523(9) . ? C22 C23 1.376(10) . ? C22 H22 0.9300 . ? C23 C24 1.384(9) . ? C23 H23 0.9300 . ? C24 C25 1.394(9) . ? C24 H24 0.9300 . ? C25 C26 1.503(9) . ? C26 C28 1.528(10) . ? C26 C27 1.547(10) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C31 1.514(9) . ? C29 C30 1.535(9) . ? C29 H29 0.9800 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? Cu1 Br1 2.4132(11) . ? Cu1 Br1 2.4429(10) 3_565 ? Cu1 Cu1 2.7178(14) 3_565 ? Br1 Cu1 2.4429(10) 3_565 ? 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 C2 C6 C7 120.9(5) . 3_465 ? C2 C6 H6 119.5 . . ? C7 C6 H6 119.5 3_465 . ? C4 C7 C6 120.4(5) . 3_465 ? C4 C7 H7 119.8 . . ? C6 C7 H7 119.8 3_465 . ? O1 C32 C33 106.5(7) . . ? O1 C32 H32A 110.4 . . ? C33 C32 H32A 110.4 . . ? O1 C32 H32B 110.4 . . ? C33 C32 H32B 110.4 . . ? H32A C32 H32B 108.6 . . ? C32 C33 C34 102.5(8) . . ? C32 C33 H33A 111.3 . . ? C34 C33 H33A 111.3 . . ? C32 C33 H33B 111.3 . . ? C34 C33 H33B 111.3 . . ? H33A C33 H33B 109.2 . . ? C35 C34 C33 103.9(8) . . ? C35 C34 H34A 111.0 . . ? C33 C34 H34A 111.0 . . ? C35 C34 H34B 111.0 . . ? C33 C34 H34B 111.0 . . ? H34A C34 H34B 109.0 . . ? O1 C35 C34 108.9(7) . . ? O1 C35 H35A 109.9 . . ? C34 C35 H35A 109.9 . . ? O1 C35 H35B 109.9 . . ? C34 C35 H35B 109.9 . . ? H35A C35 H35B 108.3 . . ? C1 N1 C8 120.0(4) . . ? C1 N1 Cu1 110.4(4) . . ? C8 N1 Cu1 129.5(3) . . ? C5 N2 C20 120.2(4) . . ? C5 N2 Cu1 110.0(4) . . ? C20 N2 Cu1 129.8(3) . . ? C35 O1 C32 108.4(6) . . ? N1 C1 C2 134.0(5) . . ? N1 C1 C5 118.6(5) . . ? C2 C1 C5 107.0(4) . . ? C6 C2 C3 117.5(5) . . ? C6 C2 C1 137.9(5) . . ? C3 C2 C1 104.6(4) . . ? C3 C3 C2 122.2(6) 3_465 . ? C3 C3 C4 121.1(6) 3_465 . ? C2 C3 C4 116.7(5) . . ? C7 C4 C3 117.9(5) . . ? C7 C4 C5 138.2(5) . . ? C3 C4 C5 103.8(4) . . ? N2 C5 C4 133.3(5) . . ? N2 C5 C1 118.5(5) . . ? C4 C5 C1 107.8(4) . . ? C13 C8 C9 121.9(5) . . ? C13 C8 N1 119.3(5) . . ? C9 C8 N1 118.8(5) . . ? C10 C9 C8 117.4(6) . . ? C10 C9 C14 121.2(6) . . ? C8 C9 C14 121.3(5) . . ? C9 C10 C11 121.9(6) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? C12 C11 C10 119.6(6) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 121.5(6) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C8 C13 C12 117.8(6) . . ? C8 C13 C17 122.2(5) . . ? C12 C13 C17 120.0(5) . . ? C15 C14 C16 112.1(6) . . ? C15 C14 C9 110.7(5) . . ? C16 C14 C9 111.4(6) . . ? C15 C14 H14 107.5 . . ? C16 C14 H14 107.5 . . ? C9 C14 H14 107.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C13 112.2(6) . . ? C18 C17 C19 111.1(6) . . ? C13 C17 C19 109.4(5) . . ? C18 C17 H17 108.0 . . ? C13 C17 H17 108.0 . . ? C19 C17 H17 108.0 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 122.6(5) . . ? C21 C20 N2 117.9(5) . . ? C25 C20 N2 119.3(5) . . ? C22 C21 C20 117.0(6) . . ? C22 C21 C29 122.0(6) . . ? C20 C21 C29 120.9(5) . . ? C23 C22 C21 122.0(6) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C22 C23 C24 119.7(6) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C23 C24 C25 121.1(6) . . ? C23 C24 H24 119.5 . . ? C25 C24 H24 119.5 . . ? C24 C25 C20 117.3(6) . . ? C24 C25 C26 120.2(6) . . ? C20 C25 C26 122.5(5) . . ? C25 C26 C28 111.5(6) . . ? C25 C26 C27 109.1(6) . . ? C28 C26 C27 111.7(6) . . ? C25 C26 H26 108.2 . . ? C28 C26 H26 108.2 . . ? C27 C26 H26 108.2 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C31 C29 C21 112.5(5) . . ? C31 C29 C30 110.6(5) . . ? C21 C29 C30 111.9(5) . . ? C31 C29 H29 107.2 . . ? C21 C29 H29 107.2 . . ? C30 C29 H29 107.2 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N1 Cu1 N2 80.52(16) . . ? N1 Cu1 Br1 126.90(13) . . ? N2 Cu1 Br1 107.24(12) . . ? N1 Cu1 Br1 113.89(13) . 3_565 ? N2 Cu1 Br1 110.19(12) . 3_565 ? Br1 Cu1 Br1 111.94(3) . 3_565 ? N1 Cu1 Cu1 153.78(13) . 3_565 ? N2 Cu1 Cu1 124.99(12) . 3_565 ? Br1 Cu1 Cu1 56.49(3) . 3_565 ? Br1 Cu1 Cu1 55.45(3) 3_565 3_565 ? Cu1 Br1 Cu1 68.06(3) . 3_565 ? 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 O1 C32 C33 C34 -31.6(12) . . . . ? C32 C33 C34 C35 27.0(12) . . . . ? C33 C34 C35 O1 -13.4(13) . . . . ? C34 C35 O1 C32 -6.3(12) . . . . ? C33 C32 O1 C35 24.4(11) . . . . ? C8 N1 C1 C2 5.0(9) . . . . ? Cu1 N1 C1 C2 -178.5(5) . . . . ? C8 N1 C1 C5 -166.6(5) . . . . ? Cu1 N1 C1 C5 9.9(6) . . . . ? C7 C6 C2 C3 -0.2(8) 3_465 . . . ? C7 C6 C2 C1 179.9(6) 3_465 . . . ? N1 C1 C2 C6 7.5(12) . . . . ? C5 C1 C2 C6 179.8(6) . . . . ? N1 C1 C2 C3 -172.4(6) . . . . ? C5 C1 C2 C3 -0.2(6) . . . . ? C6 C2 C3 C3 -0.4(10) . . . 3_465 ? C1 C2 C3 C3 179.5(7) . . . 3_465 ? C6 C2 C3 C4 179.5(5) . . . . ? C1 C2 C3 C4 -0.6(6) . . . . ? C6 C7 C4 C3 1.7(8) 3_465 . . . ? C6 C7 C4 C5 178.7(6) 3_465 . . . ? C3 C3 C4 C7 -1.2(10) 3_465 . . . ? C2 C3 C4 C7 178.9(5) . . . . ? C3 C3 C4 C5 -179.1(6) 3_465 . . . ? C2 C3 C4 C5 1.0(6) . . . . ? C20 N2 C5 C4 -5.1(9) . . . . ? Cu1 N2 C5 C4 177.5(5) . . . . ? C20 N2 C5 C1 167.3(5) . . . . ? Cu1 N2 C5 C1 -10.2(6) . . . . ? C7 C4 C5 N2 -5.3(12) . . . . ? C3 C4 C5 N2 171.9(6) . . . . ? C7 C4 C5 C1 -178.2(6) . . . . ? C3 C4 C5 C1 -1.0(6) . . . . ? N1 C1 C5 N2 0.3(8) . . . . ? C2 C1 C5 N2 -173.4(5) . . . . ? N1 C1 C5 C4 174.4(5) . . . . ? C2 C1 C5 C4 0.7(6) . . . . ? C1 N1 C8 C13 75.8(7) . . . . ? Cu1 N1 C8 C13 -100.0(5) . . . . ? C1 N1 C8 C9 -106.9(6) . . . . ? Cu1 N1 C8 C9 77.4(6) . . . . ? C13 C8 C9 C10 -0.4(8) . . . . ? N1 C8 C9 C10 -177.7(5) . . . . ? C13 C8 C9 C14 -176.9(5) . . . . ? N1 C8 C9 C14 5.8(8) . . . . ? C8 C9 C10 C11 1.1(9) . . . . ? C14 C9 C10 C11 177.5(6) . . . . ? C9 C10 C11 C12 -0.5(10) . . . . ? C10 C11 C12 C13 -0.7(10) . . . . ? C9 C8 C13 C12 -0.7(8) . . . . ? N1 C8 C13 C12 176.6(5) . . . . ? C9 C8 C13 C17 -179.6(5) . . . . ? N1 C8 C13 C17 -2.3(7) . . . . ? C11 C12 C13 C8 1.2(9) . . . . ? C11 C12 C13 C17 -179.8(6) . . . . ? C10 C9 C14 C15 -75.4(8) . . . . ? C8 C9 C14 C15 101.0(7) . . . . ? C10 C9 C14 C16 50.1(8) . . . . ? C8 C9 C14 C16 -133.6(6) . . . . ? C8 C13 C17 C18 -134.2(6) . . . . ? C12 C13 C17 C18 46.9(8) . . . . ? C8 C13 C17 C19 102.0(7) . . . . ? C12 C13 C17 C19 -76.8(7) . . . . ? C5 N2 C20 C21 -88.7(6) . . . . ? Cu1 N2 C20 C21 88.2(6) . . . . ? C5 N2 C20 C25 95.8(6) . . . . ? Cu1 N2 C20 C25 -87.3(6) . . . . ? C25 C20 C21 C22 -5.2(8) . . . . ? N2 C20 C21 C22 179.4(5) . . . . ? C25 C20 C21 C29 172.9(5) . . . . ? N2 C20 C21 C29 -2.4(7) . . . . ? C20 C21 C22 C23 2.8(9) . . . . ? C29 C21 C22 C23 -175.3(6) . . . . ? C21 C22 C23 C24 1.1(10) . . . . ? C22 C23 C24 C25 -2.8(10) . . . . ? C23 C24 C25 C20 0.5(9) . . . . ? C23 C24 C25 C26 178.3(6) . . . . ? C21 C20 C25 C24 3.6(8) . . . . ? N2 C20 C25 C24 178.9(5) . . . . ? C21 C20 C25 C26 -174.2(5) . . . . ? N2 C20 C25 C26 1.1(8) . . . . ? C24 C25 C26 C28 62.9(8) . . . . ? C20 C25 C26 C28 -119.3(6) . . . . ? C24 C25 C26 C27 -60.9(8) . . . . ? C20 C25 C26 C27 116.9(6) . . . . ? C22 C21 C29 C31 39.0(8) . . . . ? C20 C21 C29 C31 -139.1(6) . . . . ? C22 C21 C29 C30 -86.2(7) . . . . ? C20 C21 C29 C30 95.7(7) . . . . ? C1 N1 Cu1 N2 -11.5(4) . . . . ? C8 N1 Cu1 N2 164.6(5) . . . . ? C1 N1 Cu1 Br1 -116.0(3) . . . . ? C8 N1 Cu1 Br1 60.1(5) . . . . ? C1 N1 Cu1 Br1 96.5(4) . . . 3_565 ? C8 N1 Cu1 Br1 -87.4(4) . . . 3_565 ? C1 N1 Cu1 Cu1 156.2(3) . . . 3_565 ? C8 N1 Cu1 Cu1 -27.7(6) . . . 3_565 ? C5 N2 Cu1 N1 11.7(4) . . . . ? C20 N2 Cu1 N1 -165.5(5) . . . . ? C5 N2 Cu1 Br1 137.5(3) . . . . ? C20 N2 Cu1 Br1 -39.7(5) . . . . ? C5 N2 Cu1 Br1 -100.4(4) . . . 3_565 ? C20 N2 Cu1 Br1 82.4(4) . . . 3_565 ? C5 N2 Cu1 Cu1 -161.7(3) . . . 3_565 ? C20 N2 Cu1 Cu1 21.1(5) . . . 3_565 ? N1 Cu1 Br1 Cu1 -148.03(16) . . . 3_565 ? N2 Cu1 Br1 Cu1 120.97(13) . . . 3_565 ? Br1 Cu1 Br1 Cu1 0.0 3_565 . . 3_565 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.207 _refine_diff_density_min -0.736 _refine_diff_density_rms 0.279