# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_wim100-new #TrackingRef '15199_web_deposit_cif_file_0_LucVanMeervelt_1352127472.wim100-NEW.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H38 Cu N4' _chemical_formula_weight 806.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.7700(4) _cell_length_b 13.5622(4) _cell_length_c 21.6416(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.943(2) _cell_angle_gamma 90.00 _cell_volume 4026.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1676 _exptl_absorpt_coefficient_mu 1.097 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 39793 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 71.48 _reflns_number_total 7712 _reflns_number_gt 6382 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+1.8201P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7712 _refine_ls_number_parameters 532 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 Cu1 Cu 0.933518(19) 0.86180(2) 0.246506(12) 0.01298(9) Uani 1 1 d . . . N2 N 0.83012(11) 0.76274(11) 0.23469(7) 0.0140(3) Uani 1 1 d . . . C3 C 0.80995(14) 0.70543(14) 0.18424(9) 0.0158(4) Uani 1 1 d . . . C4 C 0.71126(14) 0.67393(15) 0.18079(9) 0.0189(4) Uani 1 1 d . . . H4 H 0.6790 0.6340 0.1493 0.023 Uiso 1 1 calc R . . C5 C 0.67155(14) 0.71197(15) 0.23145(10) 0.0185(4) Uani 1 1 d . . . H5 H 0.6064 0.7033 0.2418 0.022 Uiso 1 1 calc R . . C6 C 0.74573(13) 0.76696(14) 0.26586(9) 0.0147(4) Uani 1 1 d . . . C7 C 0.73864(14) 0.81607(14) 0.32214(9) 0.0155(4) Uani 1 1 d . . . C8 C 0.80852(14) 0.87989(14) 0.35143(9) 0.0151(4) Uani 1 1 d . . . C9 C 0.80835(14) 0.92040(15) 0.41194(9) 0.0188(4) Uani 1 1 d . . . H9 H 0.7610 0.9089 0.4406 0.023 Uiso 1 1 calc R . . C10 C 0.88936(15) 0.97929(14) 0.42127(9) 0.0184(4) Uani 1 1 d . . . H10 H 0.9094 1.0153 0.4578 0.022 Uiso 1 1 calc R . . C11 C 0.93749(14) 0.97617(14) 0.36599(9) 0.0159(4) Uani 1 1 d . . . N12 N 0.89030(11) 0.91515(11) 0.32419(7) 0.0134(3) Uani 1 1 d . . . C13 C 0.88209(15) 0.67464(14) 0.14239(9) 0.0187(4) Uani 1 1 d . . . C14 C 0.85171(18) 0.65020(16) 0.08079(10) 0.0254(5) Uani 1 1 d . . . H14 H 0.7848 0.6560 0.0664 0.031 Uiso 1 1 calc R . . C15 C 0.9178(2) 0.61779(18) 0.04072(11) 0.0332(5) Uani 1 1 d . . . H15 H 0.8959 0.6011 -0.0008 0.040 Uiso 1 1 calc R . . C16 C 1.0152(2) 0.60961(17) 0.06068(12) 0.0340(6) Uani 1 1 d . . . H16 H 1.0606 0.5891 0.0326 0.041 Uiso 1 1 calc R . . C17 C 1.04701(18) 0.63140(17) 0.12188(13) 0.0320(5) Uani 1 1 d . . . H17 H 1.1139 0.6240 0.1359 0.038 Uiso 1 1 calc R . . C18 C 0.98080(15) 0.66412(15) 0.16268(11) 0.0227(4) Uani 1 1 d . . . H18 H 1.0028 0.6793 0.2044 0.027 Uiso 1 1 calc R . . C19 C 0.64750(14) 0.79722(15) 0.35284(9) 0.0170(4) Uani 1 1 d . . . C20 C 0.62427(15) 0.70126(15) 0.36992(10) 0.0203(4) Uani 1 1 d . . . H20 H 0.6688 0.6492 0.3642 0.024 Uiso 1 1 calc R . . C21 C 0.53703(16) 0.68091(16) 0.39509(10) 0.0230(4) Uani 1 1 d . . . H21 H 0.5222 0.6155 0.4068 0.028 Uiso 1 1 calc R . . C22 C 0.47149(15) 0.75709(17) 0.40307(10) 0.0241(4) Uani 1 1 d . . . H22 H 0.4113 0.7435 0.4197 0.029 Uiso 1 1 calc R . . C23 C 0.49382(15) 0.85267(16) 0.38682(10) 0.0227(4) Uani 1 1 d . . . H23 H 0.4489 0.9044 0.3924 0.027 Uiso 1 1 calc R . . C24 C 0.58211(15) 0.87332(15) 0.36232(10) 0.0195(4) Uani 1 1 d . . . H24 H 0.5977 0.9392 0.3521 0.023 Uiso 1 1 calc R . . C25 C 1.02130(14) 1.03762(14) 0.35277(9) 0.0167(4) Uani 1 1 d . . . C26 C 1.03696(14) 1.06862(14) 0.29299(10) 0.0183(4) Uani 1 1 d . . . H26 H 0.9943 1.0470 0.2588 0.022 Uiso 1 1 calc R . . C27 C 1.11407(16) 1.13074(16) 0.28276(11) 0.0240(4) Uani 1 1 d . . . H27 H 1.1239 1.1511 0.2418 0.029 Uiso 1 1 calc R . . C28 C 1.17673(17) 1.16324(17) 0.33212(12) 0.0311(5) Uani 1 1 d . . . H28 H 1.2296 1.2056 0.3250 0.037 Uiso 1 1 calc R . . C29 C 1.16202(19) 1.13379(18) 0.39167(12) 0.0336(5) Uani 1 1 d . . . H29 H 1.2049 1.1561 0.4255 0.040 Uiso 1 1 calc R . . C30 C 1.08480(16) 1.07158(16) 0.40245(11) 0.0254(5) Uani 1 1 d . . . H30 H 1.0750 1.0520 0.4436 0.031 Uiso 1 1 calc R . . N31 N 0.93230(11) 0.90643(11) 0.16067(7) 0.0129(3) Uani 1 1 d . . . C32 C 0.85316(13) 0.91993(13) 0.12028(9) 0.0143(4) Uani 1 1 d . . . C33 C 0.88099(14) 0.92588(14) 0.05878(9) 0.0168(4) Uani 1 1 d . . . H33 H 0.8388 0.9335 0.0220 0.020 Uiso 1 1 calc R . . C34 C 0.98119(14) 0.91850(14) 0.06279(9) 0.0165(4) Uani 1 1 d . . . H34 H 1.0213 0.9209 0.0292 0.020 Uiso 1 1 calc R . . C35 C 1.01331(14) 0.90658(13) 0.12641(9) 0.0148(4) Uani 1 1 d . . . C36 C 1.11007(14) 0.90116(14) 0.15344(9) 0.0153(4) Uani 1 1 d . . . C37 C 1.13958(14) 0.88045(14) 0.21554(9) 0.0153(4) Uani 1 1 d . . . C38 C 1.23725(14) 0.87546(15) 0.24379(10) 0.0192(4) Uani 1 1 d . . . H38 H 1.2949 0.8904 0.2245 0.023 Uiso 1 1 calc R . . C39 C 1.23245(14) 0.84532(16) 0.30353(10) 0.0209(4) Uani 1 1 d . . . H39 H 1.2859 0.8361 0.3338 0.025 Uiso 1 1 calc R . . C40 C 1.13227(14) 0.83028(14) 0.31196(9) 0.0165(4) Uani 1 1 d . . . N41 N 1.07667(11) 0.85261(11) 0.25962(7) 0.0137(3) Uani 1 1 d . . . C42 C 0.75426(14) 0.93484(14) 0.13989(9) 0.0152(4) Uani 1 1 d . . . C43 C 0.67263(14) 0.90185(15) 0.10264(10) 0.0195(4) Uani 1 1 d . . . H43 H 0.6808 0.8683 0.0649 0.023 Uiso 1 1 calc R . . C44 C 0.57973(15) 0.91800(17) 0.12074(10) 0.0238(4) Uani 1 1 d . . . H44 H 0.5247 0.8946 0.0955 0.029 Uiso 1 1 calc R . . C45 C 0.56613(15) 0.96807(16) 0.17539(10) 0.0228(4) Uani 1 1 d . . . H45 H 0.5023 0.9787 0.1875 0.027 Uiso 1 1 calc R . . C46 C 0.64652(15) 1.00226(15) 0.21197(10) 0.0202(4) Uani 1 1 d . . . H46 H 0.6378 1.0372 0.2491 0.024 Uiso 1 1 calc R . . C47 C 0.73991(14) 0.98569(14) 0.19457(9) 0.0166(4) Uani 1 1 d . . . H47 H 0.7946 1.0091 0.2201 0.020 Uiso 1 1 calc R . . C48 C 1.18832(13) 0.92010(14) 0.11088(9) 0.0159(4) Uani 1 1 d . . . C49 C 1.20228(14) 0.85531(15) 0.06226(10) 0.0186(4) Uani 1 1 d . . . H49 H 1.1617 0.7989 0.0560 0.022 Uiso 1 1 calc R . . C50 C 1.27511(15) 0.87260(16) 0.02285(10) 0.0222(4) Uani 1 1 d . . . H50 H 1.2843 0.8281 -0.0100 0.027 Uiso 1 1 calc R . . C51 C 1.33438(14) 0.95532(17) 0.03172(10) 0.0232(4) Uani 1 1 d . . . H51 H 1.3846 0.9668 0.0051 0.028 Uiso 1 1 calc R . . C52 C 1.32040(15) 1.02092(17) 0.07914(10) 0.0240(4) Uani 1 1 d . . . H52 H 1.3604 1.0778 0.0847 0.029 Uiso 1 1 calc R . . C53 C 1.24746(14) 1.00352(16) 0.11894(10) 0.0206(4) Uani 1 1 d . . . H53 H 1.2381 1.0486 0.1515 0.025 Uiso 1 1 calc R . . C54 C 1.09180(14) 0.79211(14) 0.36806(9) 0.0161(4) Uani 1 1 d . . . C55 C 1.00932(14) 0.73088(14) 0.36362(9) 0.0171(4) Uani 1 1 d . . . H55 H 0.9815 0.7104 0.3240 0.021 Uiso 1 1 calc R . . C56 C 0.96813(15) 0.70011(15) 0.41649(10) 0.0199(4) Uani 1 1 d . . . H56 H 0.9117 0.6595 0.4129 0.024 Uiso 1 1 calc R . . C57 C 1.00870(16) 0.72824(16) 0.47467(10) 0.0224(4) Uani 1 1 d . . . H57 H 0.9791 0.7087 0.5108 0.027 Uiso 1 1 calc R . . C58 C 1.09300(16) 0.78527(15) 0.47996(10) 0.0220(4) Uani 1 1 d . . . H58 H 1.1224 0.8026 0.5198 0.026 Uiso 1 1 calc R . . C59 C 1.13429(14) 0.81696(15) 0.42691(10) 0.0193(4) Uani 1 1 d . . . H59 H 1.1919 0.8558 0.4308 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01191(14) 0.01519(15) 0.01193(15) -0.00046(10) 0.00157(10) -0.00210(10) N2 0.0139(7) 0.0130(7) 0.0153(8) 0.0005(6) 0.0026(6) -0.0009(6) C3 0.0198(9) 0.0117(8) 0.0157(9) 0.0005(7) 0.0005(7) -0.0022(7) C4 0.0204(10) 0.0180(9) 0.0179(10) -0.0006(7) -0.0012(8) -0.0044(8) C5 0.0161(9) 0.0175(9) 0.0217(10) 0.0018(7) 0.0012(7) -0.0033(8) C6 0.0137(8) 0.0135(8) 0.0174(10) 0.0027(7) 0.0036(7) 0.0000(7) C7 0.0160(9) 0.0127(8) 0.0181(10) 0.0047(7) 0.0022(7) 0.0026(7) C8 0.0158(9) 0.0138(9) 0.0162(9) 0.0025(7) 0.0038(7) 0.0036(7) C9 0.0219(10) 0.0181(9) 0.0171(10) 0.0025(7) 0.0056(8) 0.0038(8) C10 0.0252(10) 0.0153(9) 0.0144(10) -0.0006(7) -0.0003(8) 0.0016(8) C11 0.0184(9) 0.0122(8) 0.0164(10) 0.0018(7) -0.0023(7) 0.0021(7) N12 0.0145(7) 0.0120(7) 0.0137(8) -0.0003(6) 0.0016(6) 0.0003(6) C13 0.0264(10) 0.0107(8) 0.0195(10) 0.0000(7) 0.0052(8) -0.0028(8) C14 0.0367(12) 0.0197(10) 0.0203(11) -0.0023(8) 0.0046(9) 0.0008(9) C15 0.0537(15) 0.0260(11) 0.0214(12) -0.0029(9) 0.0124(10) 0.0016(11) C16 0.0495(15) 0.0195(10) 0.0371(14) -0.0062(9) 0.0268(11) -0.0017(10) C17 0.0283(12) 0.0206(11) 0.0494(15) -0.0067(10) 0.0167(11) -0.0020(9) C18 0.0236(10) 0.0171(10) 0.0284(12) -0.0059(8) 0.0082(8) -0.0036(8) C19 0.0165(9) 0.0177(9) 0.0172(10) 0.0004(7) 0.0034(7) -0.0004(8) C20 0.0234(10) 0.0168(9) 0.0215(10) 0.0023(8) 0.0061(8) 0.0029(8) C21 0.0270(11) 0.0177(10) 0.0255(11) 0.0018(8) 0.0082(9) -0.0038(9) C22 0.0194(10) 0.0272(11) 0.0271(11) 0.0009(9) 0.0099(8) -0.0018(9) C23 0.0206(10) 0.0214(10) 0.0270(11) -0.0006(8) 0.0072(8) 0.0035(8) C24 0.0210(10) 0.0154(9) 0.0229(11) 0.0015(8) 0.0064(8) 0.0009(8) C25 0.0175(9) 0.0111(8) 0.0211(10) -0.0006(7) -0.0007(7) 0.0011(7) C26 0.0176(9) 0.0137(9) 0.0230(10) -0.0004(7) -0.0008(7) 0.0022(8) C27 0.0234(10) 0.0193(10) 0.0296(12) 0.0055(8) 0.0037(8) -0.0010(8) C28 0.0236(11) 0.0244(11) 0.0446(15) 0.0049(10) -0.0022(10) -0.0106(9) C29 0.0358(13) 0.0264(11) 0.0358(14) 0.0014(10) -0.0128(10) -0.0122(10) C30 0.0310(11) 0.0210(10) 0.0227(11) 0.0015(8) -0.0065(9) -0.0057(9) N31 0.0147(7) 0.0123(7) 0.0121(8) 0.0013(6) 0.0022(6) -0.0007(6) C32 0.0160(9) 0.0103(8) 0.0165(9) 0.0007(7) 0.0008(7) -0.0011(7) C33 0.0186(9) 0.0174(9) 0.0140(10) 0.0010(7) -0.0007(7) 0.0017(8) C34 0.0198(9) 0.0138(9) 0.0167(10) 0.0016(7) 0.0056(7) 0.0015(8) C35 0.0169(9) 0.0115(8) 0.0166(9) 0.0015(7) 0.0049(7) 0.0002(7) C36 0.0173(9) 0.0114(8) 0.0179(10) -0.0007(7) 0.0046(7) 0.0001(7) C37 0.0140(9) 0.0135(8) 0.0189(10) -0.0002(7) 0.0041(7) -0.0002(7) C38 0.0135(9) 0.0227(10) 0.0215(10) 0.0002(8) 0.0012(7) -0.0003(8) C39 0.0149(9) 0.0261(10) 0.0211(11) 0.0025(8) -0.0013(7) 0.0003(8) C40 0.0166(9) 0.0151(9) 0.0173(10) -0.0011(7) -0.0002(7) -0.0001(7) N41 0.0131(7) 0.0134(7) 0.0146(8) 0.0005(6) 0.0008(6) 0.0008(6) C42 0.0166(9) 0.0115(8) 0.0175(10) 0.0037(7) 0.0013(7) 0.0002(7) C43 0.0200(10) 0.0189(9) 0.0190(10) -0.0014(8) -0.0011(8) 0.0001(8) C44 0.0163(9) 0.0273(11) 0.0269(11) -0.0023(9) -0.0039(8) -0.0012(8) C45 0.0170(9) 0.0224(10) 0.0296(12) 0.0018(8) 0.0055(8) 0.0032(8) C46 0.0244(10) 0.0176(9) 0.0190(10) -0.0008(7) 0.0047(8) 0.0037(8) C47 0.0175(9) 0.0140(9) 0.0179(10) 0.0008(7) -0.0011(7) 0.0005(7) C48 0.0140(8) 0.0170(9) 0.0169(10) 0.0035(7) 0.0017(7) 0.0017(7) C49 0.0179(9) 0.0175(9) 0.0207(10) 0.0022(8) 0.0032(7) 0.0012(8) C50 0.0206(10) 0.0267(11) 0.0200(10) 0.0016(8) 0.0061(8) 0.0063(8) C51 0.0162(9) 0.0332(12) 0.0214(11) 0.0094(9) 0.0076(8) 0.0031(9) C52 0.0185(10) 0.0260(11) 0.0274(12) 0.0072(9) 0.0015(8) -0.0046(8) C53 0.0175(9) 0.0229(10) 0.0216(11) 0.0001(8) 0.0021(8) -0.0025(8) C54 0.0171(9) 0.0131(9) 0.0181(10) 0.0016(7) 0.0006(7) 0.0036(7) C55 0.0181(9) 0.0156(9) 0.0173(10) 0.0008(7) -0.0005(7) 0.0028(8) C56 0.0190(9) 0.0166(9) 0.0246(11) 0.0051(8) 0.0043(8) 0.0016(8) C57 0.0270(10) 0.0211(10) 0.0202(11) 0.0063(8) 0.0079(8) 0.0054(9) C58 0.0305(11) 0.0188(10) 0.0160(10) -0.0006(7) -0.0021(8) 0.0046(9) C59 0.0198(9) 0.0176(9) 0.0199(10) 0.0018(8) -0.0019(8) 0.0009(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N31 1.9524(16) . ? Cu1 N2 1.9582(16) . ? Cu1 N12 1.9690(16) . ? Cu1 N41 1.9711(15) . ? N2 C3 1.350(3) . ? N2 C6 1.394(2) . ? C3 C4 1.420(3) . ? C3 C13 1.462(3) . ? C4 C5 1.368(3) . ? C4 H4 0.9500 . ? C5 C6 1.422(3) . ? C5 H5 0.9500 . ? C6 C7 1.399(3) . ? C7 C8 1.404(3) . ? C7 C19 1.492(3) . ? C8 N12 1.399(2) . ? C8 C9 1.420(3) . ? C9 C10 1.373(3) . ? C9 H9 0.9500 . ? C10 C11 1.417(3) . ? C10 H10 0.9500 . ? C11 N12 1.351(2) . ? C11 C25 1.471(3) . ? C13 C18 1.399(3) . ? C13 C14 1.402(3) . ? C14 C15 1.381(3) . ? C14 H14 0.9500 . ? C15 C16 1.378(4) . ? C15 H15 0.9500 . ? C16 C17 1.390(4) . ? C16 H16 0.9500 . ? C17 C18 1.395(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.396(3) . ? C19 C20 1.398(3) . ? C20 C21 1.389(3) . ? C20 H20 0.9500 . ? C21 C22 1.392(3) . ? C21 H21 0.9500 . ? C22 C23 1.385(3) . ? C22 H22 0.9500 . ? C23 C24 1.396(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.395(3) . ? C25 C30 1.404(3) . ? C26 C27 1.388(3) . ? C26 H26 0.9500 . ? C27 C28 1.386(3) . ? C27 H27 0.9500 . ? C28 C29 1.381(4) . ? C28 H28 0.9500 . ? C29 C30 1.393(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? N31 C32 1.350(2) . ? N31 C35 1.392(2) . ? C32 C33 1.419(3) . ? C32 C42 1.475(3) . ? C33 C34 1.379(3) . ? C33 H33 0.9500 . ? C34 C35 1.419(3) . ? C34 H34 0.9500 . ? C35 C36 1.410(3) . ? C36 C37 1.399(3) . ? C36 C48 1.499(3) . ? C37 N41 1.395(2) . ? C37 C38 1.430(3) . ? C38 C39 1.363(3) . ? C38 H38 0.9500 . ? C39 C40 1.422(3) . ? C39 H39 0.9500 . ? C40 N41 1.346(3) . ? C40 C54 1.473(3) . ? C42 C47 1.398(3) . ? C42 C43 1.399(3) . ? C43 C44 1.387(3) . ? C43 H43 0.9500 . ? C44 C45 1.390(3) . ? C44 H44 0.9500 . ? C45 C46 1.384(3) . ? C45 H45 0.9500 . ? C46 C47 1.389(3) . ? C46 H46 0.9500 . ? C47 H47 0.9500 . ? C48 C53 1.396(3) . ? C48 C49 1.397(3) . ? C49 C50 1.391(3) . ? C49 H49 0.9500 . ? C50 C51 1.391(3) . ? C50 H50 0.9500 . ? C51 C52 1.384(3) . ? C51 H51 0.9500 . ? C52 C53 1.398(3) . ? C52 H52 0.9500 . ? C53 H53 0.9500 . ? C54 C59 1.396(3) . ? C54 C55 1.404(3) . ? C55 C56 1.385(3) . ? C55 H55 0.9500 . ? C56 C57 1.386(3) . ? C56 H56 0.9500 . ? C57 C58 1.391(3) . ? C57 H57 0.9500 . ? C58 C59 1.392(3) . ? C58 H58 0.9500 . ? C59 H59 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N31 Cu1 N2 98.16(7) . . ? N31 Cu1 N12 136.06(7) . . ? N2 Cu1 N12 95.38(7) . . ? N31 Cu1 N41 94.76(7) . . ? N2 Cu1 N41 133.02(7) . . ? N12 Cu1 N41 105.81(7) . . ? C3 N2 C6 107.05(16) . . ? C3 N2 Cu1 126.68(13) . . ? C6 N2 Cu1 122.39(13) . . ? N2 C3 C4 110.18(17) . . ? N2 C3 C13 124.23(17) . . ? C4 C3 C13 125.44(18) . . ? C5 C4 C3 106.94(17) . . ? C5 C4 H4 126.5 . . ? C3 C4 H4 126.5 . . ? C4 C5 C6 107.38(17) . . ? C4 C5 H5 126.3 . . ? C6 C5 H5 126.3 . . ? N2 C6 C7 124.36(17) . . ? N2 C6 C5 108.43(17) . . ? C7 C6 C5 127.20(18) . . ? C6 C7 C8 126.16(18) . . ? C6 C7 C19 115.51(17) . . ? C8 C7 C19 118.34(17) . . ? N12 C8 C7 124.43(17) . . ? N12 C8 C9 108.76(17) . . ? C7 C8 C9 126.81(18) . . ? C10 C9 C8 107.15(17) . . ? C10 C9 H9 126.4 . . ? C8 C9 H9 126.4 . . ? C9 C10 C11 106.95(17) . . ? C9 C10 H10 126.5 . . ? C11 C10 H10 126.5 . . ? N12 C11 C10 110.52(17) . . ? N12 C11 C25 123.86(18) . . ? C10 C11 C25 125.36(18) . . ? C11 N12 C8 106.59(16) . . ? C11 N12 Cu1 129.32(13) . . ? C8 N12 Cu1 123.20(13) . . ? C18 C13 C14 118.5(2) . . ? C18 C13 C3 121.89(19) . . ? C14 C13 C3 119.58(19) . . ? C15 C14 C13 120.9(2) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C16 C15 C14 120.3(2) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 120.0(2) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C18 120.1(2) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C13 120.3(2) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? C24 C19 C20 118.96(18) . . ? C24 C19 C7 121.11(18) . . ? C20 C19 C7 119.86(17) . . ? C21 C20 C19 120.95(19) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 119.54(19) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C23 C22 C21 120.18(19) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 120.26(19) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C19 120.08(19) . . ? C23 C24 H24 120.0 . . ? C19 C24 H24 120.0 . . ? C26 C25 C30 118.41(19) . . ? C26 C25 C11 122.51(18) . . ? C30 C25 C11 118.96(19) . . ? C27 C26 C25 120.82(19) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C28 C27 C26 120.3(2) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C29 C28 C27 119.7(2) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C30 120.5(2) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C29 C30 C25 120.3(2) . . ? C29 C30 H30 119.8 . . ? C25 C30 H30 119.8 . . ? C32 N31 C35 107.11(16) . . ? C32 N31 Cu1 126.77(13) . . ? C35 N31 Cu1 124.46(13) . . ? N31 C32 C33 110.31(16) . . ? N31 C32 C42 123.12(17) . . ? C33 C32 C42 126.36(17) . . ? C34 C33 C32 106.66(17) . . ? C34 C33 H33 126.7 . . ? C32 C33 H33 126.7 . . ? C33 C34 C35 107.21(17) . . ? C33 C34 H34 126.4 . . ? C35 C34 H34 126.4 . . ? N31 C35 C36 123.43(17) . . ? N31 C35 C34 108.67(16) . . ? C36 C35 C34 127.80(17) . . ? C37 C36 C35 126.51(18) . . ? C37 C36 C48 117.40(17) . . ? C35 C36 C48 116.09(17) . . ? N41 C37 C36 124.43(17) . . ? N41 C37 C38 108.15(17) . . ? C36 C37 C38 127.21(18) . . ? C39 C38 C37 107.39(18) . . ? C39 C38 H38 126.3 . . ? C37 C38 H38 126.3 . . ? C38 C39 C40 106.95(18) . . ? C38 C39 H39 126.5 . . ? C40 C39 H39 126.5 . . ? N41 C40 C39 110.35(17) . . ? N41 C40 C54 123.00(17) . . ? C39 C40 C54 126.61(18) . . ? C40 N41 C37 107.14(15) . . ? C40 N41 Cu1 128.66(13) . . ? C37 N41 Cu1 123.84(13) . . ? C47 C42 C43 118.70(18) . . ? C47 C42 C32 120.83(17) . . ? C43 C42 C32 120.42(18) . . ? C44 C43 C42 120.11(19) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C43 C44 C45 120.82(19) . . ? C43 C44 H44 119.6 . . ? C45 C44 H44 119.6 . . ? C46 C45 C44 119.37(19) . . ? C46 C45 H45 120.3 . . ? C44 C45 H45 120.3 . . ? C45 C46 C47 120.28(19) . . ? C45 C46 H46 119.9 . . ? C47 C46 H46 119.9 . . ? C46 C47 C42 120.72(18) . . ? C46 C47 H47 119.6 . . ? C42 C47 H47 119.6 . . ? C53 C48 C49 119.16(18) . . ? C53 C48 C36 120.30(18) . . ? C49 C48 C36 120.53(17) . . ? C50 C49 C48 120.60(19) . . ? C50 C49 H49 119.7 . . ? C48 C49 H49 119.7 . . ? C51 C50 C49 119.8(2) . . ? C51 C50 H50 120.1 . . ? C49 C50 H50 120.1 . . ? C52 C51 C50 120.22(18) . . ? C52 C51 H51 119.9 . . ? C50 C51 H51 119.9 . . ? C51 C52 C53 120.1(2) . . ? C51 C52 H52 120.0 . . ? C53 C52 H52 120.0 . . ? C48 C53 C52 120.1(2) . . ? C48 C53 H53 119.9 . . ? C52 C53 H53 119.9 . . ? C59 C54 C55 118.58(18) . . ? C59 C54 C40 120.57(18) . . ? C55 C54 C40 120.85(18) . . ? C56 C55 C54 120.55(19) . . ? C56 C55 H55 119.7 . . ? C54 C55 H55 119.7 . . ? C55 C56 C57 120.40(19) . . ? C55 C56 H56 119.8 . . ? C57 C56 H56 119.8 . . ? C56 C57 C58 119.71(19) . . ? C56 C57 H57 120.1 . . ? C58 C57 H57 120.1 . . ? C57 C58 C59 120.06(19) . . ? C57 C58 H58 120.0 . . ? C59 C58 H58 120.0 . . ? C58 C59 C54 120.59(19) . . ? C58 C59 H59 119.7 . . ? C54 C59 H59 119.7 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 71.48 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.504 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 909364' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_wim96 #TrackingRef 'web_deposit_cif_file_1_LucVanMeervelt_1352127472.wim96.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 Cu N4' _chemical_formula_sum 'C30 H22 Cu N4' _chemical_formula_weight 502.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 17.0388(7) _cell_length_b 15.6229(7) _cell_length_c 19.7025(7) _cell_angle_alpha 90.00 _cell_angle_beta 115.496(2) _cell_angle_gamma 90.00 _cell_volume 4734.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 47625 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 71.30 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2072 _exptl_absorpt_coefficient_mu 1.500 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.671 _exptl_absorpt_correction_T_max 0.861 _exptl_absorpt_process_details 'Bruker SADABS (SADABS, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'crossed Goebel mirrors' _diffrn_measurement_device_type 'SMART 6000' _diffrn_measurement_method 'omega and phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 47610 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 71.30 _reflns_number_total 9195 _reflns_number_gt 6864 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (SMART, 1997)' _computing_cell_refinement 'Bruker SAINT (SAINT, 1997)' _computing_data_reduction 'Bruker SAINT (SAINT, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 1998)' _computing_publication_material 'PLATON (Spek, 1998)' _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^)+(0.0608P)^2^+1.6118P] 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 9195 _refine_ls_number_parameters 632 _refine_ls_number_restraints 339 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.074 _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 Cu1 Cu 0.01393(5) 0.93735(7) 0.25313(7) 0.01506(15) Uani 1 1 d . . . N2 N 0.0221(4) 0.8587(3) 0.3328(3) 0.0167(12) Uani 1 1 d . . . C3 C -0.0176(5) 0.7824(4) 0.3227(4) 0.0217(13) Uani 1 1 d U . . H3 H -0.0496 0.7576 0.2759 0.026 Uiso 1 1 calc R . . C4 C -0.0056(5) 0.7453(4) 0.3899(4) 0.0291(14) Uani 1 1 d U . . H4 H -0.0285 0.6935 0.3961 0.035 Uiso 1 1 calc R . . C5 C 0.0481(4) 0.8010(4) 0.4473(4) 0.0230(12) Uani 1 1 d U . . H5 H 0.0692 0.7927 0.4989 0.028 Uiso 1 1 calc R . . C6 C 0.0637(4) 0.8734(4) 0.4095(4) 0.0146(11) Uani 1 1 d U . . C7 C 0.1042(5) 0.9490(4) 0.4433(4) 0.0168(11) Uani 1 1 d U . . C8 C 0.1127(4) 1.0221(4) 0.4035(4) 0.0160(11) Uani 1 1 d U . . C9 C 0.1587(4) 1.0977(4) 0.4335(4) 0.0218(12) Uani 1 1 d U . . H9 H 0.1865 1.1117 0.4843 0.026 Uiso 1 1 calc R . . C10 C 0.1555(4) 1.1472(4) 0.3754(4) 0.0248(13) Uani 1 1 d U . . H10 H 0.1810 1.2006 0.3789 0.030 Uiso 1 1 calc R . . C11 C 0.1049(5) 1.1005(4) 0.3077(4) 0.0209(13) Uani 1 1 d U . . H11 H 0.0929 1.1191 0.2594 0.025 Uiso 1 1 calc R . . N12 N 0.0769(4) 1.0246(3) 0.3244(3) 0.0191(12) Uani 1 1 d . . . C13 C 0.1452(5) 0.9544(4) 0.5273(4) 0.0176(12) Uani 1 1 d . . . C14 C 0.2068(5) 0.8979(4) 0.5708(4) 0.0255(15) Uani 1 1 d . . . H14 H 0.2246 0.8553 0.5475 0.031 Uiso 1 1 calc R . . C15 C 0.2441(5) 0.9015(4) 0.6485(4) 0.0285(15) Uani 1 1 d . . . H15 H 0.2867 0.8623 0.6767 0.034 Uiso 1 1 calc R . . C16 C 0.2174(5) 0.9646(5) 0.6845(4) 0.0309(15) Uani 1 1 d . . . H16 H 0.2419 0.9684 0.7367 0.037 Uiso 1 1 calc R . . C17 C 0.1531(5) 1.0215(5) 0.6399(4) 0.0314(15) Uani 1 1 d . . . H17 H 0.1343 1.0632 0.6632 0.038 Uiso 1 1 calc R . . C18 C 0.1166(4) 1.0187(4) 0.5632(4) 0.0250(14) Uani 1 1 d . . . H18 H 0.0739 1.0578 0.5349 0.030 Uiso 1 1 calc R . . N19 N 0.0124(4) 0.8501(3) 0.1802(3) 0.0145(11) Uani 1 1 d . . . C20 C 0.0580(5) 0.7790(4) 0.1973(4) 0.0229(12) Uani 1 1 d U . . H20 H 0.0946 0.7624 0.2461 0.027 Uiso 1 1 calc R . . C21 C 0.0447(4) 0.7311(4) 0.1329(4) 0.0250(12) Uani 1 1 d U . . H21 H 0.0697 0.6787 0.1313 0.030 Uiso 1 1 calc R . . C22 C -0.0131(4) 0.7777(4) 0.0725(4) 0.0230(12) Uani 1 1 d U . . H22 H -0.0348 0.7626 0.0220 0.028 Uiso 1 1 calc R . . C23 C -0.0333(5) 0.8546(4) 0.1030(4) 0.0189(11) Uani 1 1 d U . . C24 C -0.0838(5) 0.9218(4) 0.0632(3) 0.0169(11) Uani 1 1 d U . . C25 C -0.1005(5) 0.9968(4) 0.0957(4) 0.0219(12) Uani 1 1 d U . . C26 C -0.1594(5) 1.0628(4) 0.0600(4) 0.0318(15) Uani 1 1 d U . . H26 H -0.1930 1.0683 0.0085 0.038 Uiso 1 1 calc R . . C27 C -0.1590(5) 1.1185(4) 0.1147(4) 0.0385(16) Uani 1 1 d U . . H27 H -0.1924 1.1676 0.1078 0.046 Uiso 1 1 calc R . . C28 C -0.0962(5) 1.0845(4) 0.1842(4) 0.0243(12) Uani 1 1 d U . . H28 H -0.0827 1.1092 0.2309 0.029 Uiso 1 1 calc R . . N29 N -0.0590(4) 1.0129(3) 0.1743(3) 0.0195(12) Uani 1 1 d . . . C30 C -0.1319(5) 0.9142(4) -0.0206(3) 0.0201(13) Uani 1 1 d . . . C31 C -0.1893(5) 0.8503(4) -0.0551(4) 0.0245(13) Uani 1 1 d . . . H31 H -0.2002 0.8101 -0.0254 0.029 Uiso 1 1 calc R . . C32 C -0.2331(5) 0.8423(5) -0.1341(4) 0.0356(16) Uani 1 1 d . . . H32 H -0.2736 0.7989 -0.1562 0.043 Uiso 1 1 calc R . . C33 C -0.2145(5) 0.8998(5) -0.1771(4) 0.0334(16) Uani 1 1 d . . . H33 H -0.2411 0.8942 -0.2292 0.040 Uiso 1 1 calc R . . C34 C -0.1572(5) 0.9656(4) -0.1452(4) 0.0278(14) Uani 1 1 d . . . H34 H -0.1468 1.0047 -0.1760 0.033 Uiso 1 1 calc R . . C35 C -0.1140(4) 0.9754(4) -0.0671(3) 0.0200(12) Uani 1 1 d . . . H35 H -0.0749 1.0200 -0.0457 0.024 Uiso 1 1 calc R . . Cu36 Cu 0.49936(8) 0.68819(7) 0.25940(3) 0.01615(16) Uani 1 1 d . . . N37 N 0.5117(4) 0.6000(3) 0.3343(3) 0.0247(14) Uani 1 1 d . . . C38 C 0.4753(5) 0.5231(4) 0.3194(4) 0.0300(17) Uani 1 1 d U . . H38 H 0.4423 0.5023 0.2711 0.036 Uiso 1 1 calc R . . C39 C 0.4924(6) 0.4781(4) 0.3838(4) 0.043(2) Uani 1 1 d . . . H39 H 0.4722 0.4235 0.3867 0.052 Uiso 1 1 calc R . . C40 C 0.5453(5) 0.5289(4) 0.4441(4) 0.0337(17) Uani 1 1 d U . . H40 H 0.5685 0.5150 0.4949 0.040 Uiso 1 1 calc R . . C41 C 0.5568(5) 0.6075(4) 0.4115(4) 0.0200(14) Uani 1 1 d . . . C42 C 0.5954(5) 0.6815(4) 0.4494(2) 0.0172(9) Uani 1 1 d . . . C43 C 0.5999(5) 0.7599(4) 0.4153(4) 0.0171(13) Uani 1 1 d . . . C44 C 0.6434(4) 0.8351(4) 0.4483(4) 0.0222(13) Uani 1 1 d . . . H44 H 0.6724 0.8454 0.4997 0.027 Uiso 1 1 calc R . . C45 C 0.6366(5) 0.8911(4) 0.3932(4) 0.0247(14) Uani 1 1 d U . . H45 H 0.6602 0.9458 0.3991 0.030 Uiso 1 1 calc R . . C46 C 0.5858(5) 0.8481(4) 0.3246(4) 0.0232(14) Uani 1 1 d . . . H46 H 0.5708 0.8714 0.2772 0.028 Uiso 1 1 calc R . . N47 N 0.5621(4) 0.7706(3) 0.3365(3) 0.0154(11) Uani 1 1 d . . . C48 C 0.6402(5) 0.6789(4) 0.5337(2) 0.0185(9) Uani 1 1 d U . . C49 C 0.7050(5) 0.6214(4) 0.5717(4) 0.0253(11) Uani 1 1 d U . . H49 H 0.7221 0.5828 0.5447 0.030 Uiso 1 1 calc R . . C50 C 0.7462(5) 0.6196(4) 0.6510(4) 0.0320(12) Uani 1 1 d U . . H50 H 0.7905 0.5805 0.6759 0.038 Uiso 1 1 calc R . . C51 C 0.7206(6) 0.6753(5) 0.6907(3) 0.0327(12) Uani 1 1 d U . . H51 H 0.7483 0.6747 0.7430 0.039 Uiso 1 1 calc R . . C52 C 0.6538(5) 0.7331(4) 0.6540(4) 0.0258(11) Uani 1 1 d U . . H52 H 0.6358 0.7698 0.6818 0.031 Uiso 1 1 calc R . . C53 C 0.6134(4) 0.7364(4) 0.5754(4) 0.0190(11) Uani 1 1 d U . . H53 H 0.5694 0.7758 0.5507 0.023 Uiso 1 1 calc R . . N54 N 0.5004(4) 0.6111(3) 0.1801(3) 0.0199(12) Uani 1 1 d . . . C55 C 0.5525(5) 0.5447(4) 0.1930(4) 0.0334(16) Uani 1 1 d U . . H55 H 0.5859 0.5218 0.2403 0.040 Uiso 1 1 calc R . . C56 C 0.5507(5) 0.5131(4) 0.1257(4) 0.0437(17) Uani 1 1 d U . . H56 H 0.5814 0.4664 0.1203 0.052 Uiso 1 1 calc R . . C57 C 0.4948(5) 0.5648(4) 0.0693(3) 0.0298(13) Uani 1 1 d U . . H57 H 0.4813 0.5606 0.0184 0.036 Uiso 1 1 calc R . . C58 C 0.4610(4) 0.6268(4) 0.1041(3) 0.0189(11) Uani 1 1 d U . . C59 C 0.4092(5) 0.6950(5) 0.0697(2) 0.0207(8) Uani 1 1 d U . . C60 C 0.3854(5) 0.7616(4) 0.1070(4) 0.0233(12) Uani 1 1 d U . . C61 C 0.3251(5) 0.8255(5) 0.0772(4) 0.0436(17) Uani 1 1 d U . . H61 H 0.2913 0.8347 0.0261 0.052 Uiso 1 1 calc R . . C62 C 0.3224(5) 0.8737(5) 0.1338(4) 0.0424(17) Uani 1 1 d U . . H62 H 0.2866 0.9203 0.1293 0.051 Uiso 1 1 calc R . . C63 C 0.3855(4) 0.8379(4) 0.2007(4) 0.0216(12) Uani 1 1 d U . . H63 H 0.3985 0.8591 0.2485 0.026 Uiso 1 1 calc R . . N64 N 0.4250(4) 0.7686(3) 0.1872(3) 0.0183(12) Uani 1 1 d . . . C65 C 0.3663(5) 0.6996(5) -0.0150(2) 0.0268(10) Uani 1 1 d U . . C66 C 0.3122(4) 0.6361(5) -0.0572(4) 0.0389(13) Uani 1 1 d U . . H66 H 0.3019 0.5888 -0.0336 0.047 Uiso 1 1 calc R . . C67 C 0.2717(4) 0.6417(5) -0.1364(4) 0.0484(15) Uani 1 1 d U . . H67 H 0.2333 0.5994 -0.1651 0.058 Uiso 1 1 calc R . . C68 C 0.2905(5) 0.7117(5) -0.1708(3) 0.0479(14) Uani 1 1 d U . . H68 H 0.2647 0.7157 -0.2229 0.057 Uiso 1 1 calc R . . C69 C 0.3469(4) 0.7753(5) -0.1283(4) 0.0433(13) Uani 1 1 d U . . H69 H 0.3593 0.8212 -0.1521 0.052 Uiso 1 1 calc R . . C70 C 0.3849(5) 0.7707(5) -0.0505(4) 0.0344(12) Uani 1 1 d U . . H70 H 0.4222 0.8137 -0.0219 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0193(5) 0.0120(2) 0.0131(3) -0.00101(19) 0.0062(5) -0.0012(4) N2 0.027(3) 0.014(2) 0.010(2) -0.0056(17) 0.008(2) -0.0029(19) C3 0.025(3) 0.017(3) 0.023(3) -0.0059(19) 0.011(2) -0.006(2) C4 0.041(3) 0.025(3) 0.027(3) -0.0092(19) 0.020(3) -0.016(2) C5 0.031(3) 0.026(2) 0.018(3) -0.0022(19) 0.016(2) -0.010(2) C6 0.015(3) 0.0183(19) 0.016(2) 0.0005(16) 0.012(2) 0.0015(17) C7 0.016(3) 0.0193(19) 0.018(3) 0.0015(17) 0.010(2) 0.0023(18) C8 0.014(3) 0.0176(19) 0.014(2) -0.0018(16) 0.004(2) -0.0008(18) C9 0.019(3) 0.020(2) 0.020(3) 0.0010(18) 0.003(2) -0.0015(18) C10 0.026(3) 0.015(2) 0.025(3) -0.0034(19) 0.002(2) -0.0122(19) C11 0.023(3) 0.014(3) 0.021(3) -0.0023(18) 0.005(2) -0.0025(19) N12 0.021(3) 0.017(2) 0.017(3) 0.0031(17) 0.005(2) 0.0013(18) C13 0.017(3) 0.020(2) 0.020(3) -0.0082(19) 0.012(2) -0.005(2) C14 0.030(4) 0.027(3) 0.026(3) -0.001(2) 0.019(3) 0.001(2) C15 0.023(3) 0.038(3) 0.025(3) 0.009(2) 0.011(3) 0.009(2) C16 0.027(4) 0.046(3) 0.015(3) -0.006(2) 0.004(3) -0.002(3) C17 0.024(3) 0.047(4) 0.023(3) -0.014(2) 0.009(3) 0.002(2) C18 0.020(3) 0.027(3) 0.026(3) -0.011(2) 0.008(2) 0.001(2) N19 0.016(2) 0.016(2) 0.016(2) -0.0040(17) 0.011(2) -0.0012(17) C20 0.030(3) 0.023(3) 0.019(2) 0.0077(18) 0.015(2) 0.006(2) C21 0.031(2) 0.025(2) 0.022(2) 0.0058(16) 0.0136(19) 0.0117(18) C22 0.029(3) 0.025(2) 0.020(2) -0.0045(18) 0.016(2) 0.0038(18) C23 0.025(3) 0.019(2) 0.017(3) -0.0022(16) 0.013(2) -0.0023(17) C24 0.016(3) 0.0199(19) 0.016(2) -0.0060(16) 0.008(2) -0.0040(16) C25 0.025(3) 0.020(2) 0.017(2) -0.0045(17) 0.005(2) 0.0008(18) C26 0.032(3) 0.031(3) 0.021(3) -0.0060(19) -0.001(2) 0.011(2) C27 0.037(3) 0.026(3) 0.027(3) -0.006(2) -0.011(2) 0.018(2) C28 0.021(3) 0.020(2) 0.019(2) -0.0035(18) -0.0027(19) 0.004(2) N29 0.018(3) 0.016(2) 0.023(3) -0.0009(19) 0.008(2) 0.0020(18) C30 0.022(3) 0.026(3) 0.016(3) 0.0040(19) 0.011(3) 0.008(2) C31 0.019(3) 0.040(3) 0.017(3) -0.010(2) 0.011(3) -0.006(2) C32 0.027(3) 0.053(4) 0.029(3) -0.022(3) 0.014(3) -0.012(3) C33 0.015(3) 0.064(4) 0.017(3) -0.015(2) 0.003(2) 0.002(3) C34 0.029(3) 0.037(3) 0.019(3) 0.000(2) 0.012(3) 0.014(2) C35 0.017(3) 0.026(3) 0.015(3) 0.0004(19) 0.005(2) 0.006(2) Cu36 0.0277(5) 0.0106(2) 0.0126(3) -0.0023(4) 0.0111(5) -0.0011(3) N37 0.052(4) 0.010(2) 0.020(3) -0.0003(17) 0.023(3) 0.001(2) C38 0.056(4) 0.018(3) 0.020(3) -0.009(2) 0.020(3) -0.008(2) C39 0.093(6) 0.016(3) 0.041(4) -0.008(2) 0.046(4) -0.008(3) C40 0.060(4) 0.019(3) 0.031(3) 0.009(2) 0.029(3) 0.006(3) C41 0.033(3) 0.018(3) 0.019(3) 0.004(2) 0.020(3) 0.005(2) C42 0.018(3) 0.023(2) 0.0174(17) 0.009(2) 0.014(3) 0.0079(18) C43 0.021(3) 0.016(2) 0.013(3) 0.0040(19) 0.006(2) 0.003(2) C44 0.018(3) 0.028(3) 0.013(3) 0.002(2) 0.000(2) 0.000(2) C45 0.027(3) 0.020(3) 0.017(3) -0.0068(19) 0.001(2) -0.012(2) C46 0.024(3) 0.018(3) 0.018(3) 0.001(2) 0.000(2) -0.004(2) N47 0.015(3) 0.016(2) 0.016(3) 0.0011(17) 0.007(2) 0.0003(18) C48 0.017(2) 0.026(2) 0.0159(14) 0.0029(18) 0.011(2) 0.0031(16) C49 0.024(3) 0.030(3) 0.028(2) 0.0088(18) 0.016(2) 0.0089(17) C50 0.025(3) 0.043(3) 0.027(2) 0.018(2) 0.0100(19) 0.0093(19) C51 0.026(2) 0.053(3) 0.0171(16) 0.012(2) 0.008(2) 0.004(2) C52 0.020(3) 0.045(3) 0.0131(18) -0.0015(18) 0.008(2) -0.0016(18) C53 0.016(3) 0.028(2) 0.0148(19) 0.0002(17) 0.0083(18) 0.0031(17) N54 0.033(3) 0.014(2) 0.017(3) -0.0032(17) 0.015(2) -0.0047(19) C55 0.064(4) 0.017(3) 0.030(3) 0.008(2) 0.030(3) 0.008(3) C56 0.084(5) 0.024(3) 0.036(3) 0.002(2) 0.037(3) 0.014(3) C57 0.052(4) 0.024(2) 0.021(3) -0.0064(18) 0.024(3) -0.0021(19) C58 0.030(3) 0.0186(19) 0.014(2) -0.0086(15) 0.016(2) -0.0115(15) C59 0.015(2) 0.0326(19) 0.0169(16) -0.0089(19) 0.009(2) -0.0093(14) C60 0.016(3) 0.041(3) 0.015(3) -0.0051(19) 0.009(2) 0.0028(18) C61 0.034(3) 0.073(4) 0.016(2) -0.002(2) 0.003(2) 0.029(3) C62 0.033(3) 0.061(4) 0.026(3) 0.000(2) 0.006(2) 0.033(3) C63 0.021(3) 0.030(3) 0.017(2) 0.0004(19) 0.010(2) 0.011(2) N64 0.021(3) 0.022(3) 0.011(2) -0.0077(17) 0.006(2) -0.0032(19) C65 0.018(2) 0.051(3) 0.0176(15) -0.0056(16) 0.0140(19) 0.0001(18) C66 0.020(3) 0.077(3) 0.025(2) -0.019(2) 0.015(2) -0.011(2) C67 0.028(3) 0.093(4) 0.025(2) -0.021(2) 0.013(2) -0.009(3) C68 0.033(3) 0.093(3) 0.0231(19) -0.0090(17) 0.017(2) 0.008(3) C69 0.024(3) 0.090(4) 0.020(2) 0.008(2) 0.013(2) 0.006(2) C70 0.022(3) 0.062(3) 0.0198(19) 0.008(2) 0.010(2) 0.006(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 Cu1 N12 1.919(6) . ? Cu1 N29 1.920(6) . ? Cu1 N2 1.950(5) . ? Cu1 N19 1.973(5) . ? N2 C3 1.343(9) . ? N2 C6 1.385(9) . ? C3 C4 1.376(10) . ? C3 H3 0.9300 . ? C4 C5 1.408(9) . ? C4 H4 0.9300 . ? C5 C6 1.441(8) . ? C5 H5 0.9300 . ? C6 C7 1.386(9) . ? C7 C8 1.428(8) . ? C7 C13 1.495(9) . ? C8 C9 1.400(9) . ? C8 N12 1.408(9) . ? C9 C10 1.363(9) . ? C9 H9 0.9300 . ? C10 C11 1.438(8) . ? C10 H10 0.9300 . ? C11 N12 1.370(9) . ? C11 H11 0.9300 . ? C13 C14 1.357(10) . ? C13 C18 1.430(8) . ? C14 C15 1.384(10) . ? C14 H14 0.9300 . ? C15 C16 1.400(10) . ? C15 H15 0.9300 . ? C16 C17 1.390(10) . ? C16 H16 0.9300 . ? C17 C18 1.364(9) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? N19 C20 1.314(9) . ? N19 C23 1.379(9) . ? C20 C21 1.406(9) . ? C20 H20 0.9300 . ? C21 C22 1.381(9) . ? C21 H21 0.9300 . ? C22 C23 1.450(8) . ? C22 H22 0.9300 . ? C23 C24 1.370(9) . ? C24 C25 1.421(8) . ? C24 C30 1.500(9) . ? C25 C26 1.400(9) . ? C25 N29 1.421(9) . ? C26 C27 1.382(9) . ? C26 H26 0.9300 . ? C27 C28 1.428(9) . ? C27 H27 0.9300 . ? C28 N29 1.340(9) . ? C28 H28 0.9300 . ? C30 C31 1.357(9) . ? C30 C35 1.444(9) . ? C31 C32 1.413(9) . ? C31 H31 0.9300 . ? C32 C33 1.364(10) . ? C32 H32 0.9300 . ? C33 C34 1.371(10) . ? C33 H33 0.9300 . ? C34 C35 1.399(8) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? Cu36 N64 1.912(6) . ? Cu36 N47 1.926(6) . ? Cu36 N37 1.964(6) . ? Cu36 N54 1.979(5) . ? N37 C38 1.325(9) . ? N37 C41 1.383(9) . ? C38 C39 1.368(10) . ? C38 H38 0.9300 . ? C39 C40 1.390(11) . ? C39 H39 0.9300 . ? C40 C41 1.437(8) . ? C40 H40 0.9300 . ? C41 C42 1.379(8) . ? C42 C43 1.415(8) . ? C42 C48 1.500(6) . ? C43 C44 1.391(9) . ? C43 N47 1.411(8) . ? C44 C45 1.359(9) . ? C44 H44 0.9300 . ? C45 C46 1.421(9) . ? C45 H45 0.9300 . ? C46 N47 1.329(9) . ? C46 H46 0.9300 . ? C48 C49 1.369(9) . ? C48 C53 1.419(8) . ? C49 C50 1.410(10) . ? C49 H49 0.9300 . ? C50 C51 1.362(10) . ? C50 H50 0.9300 . ? C51 C52 1.387(10) . ? C51 H51 0.9300 . ? C52 C53 1.400(9) . ? C52 H52 0.9300 . ? C53 H53 0.9300 . ? N54 C55 1.316(9) . ? N54 C58 1.374(8) . ? C55 C56 1.403(9) . ? C55 H55 0.9300 . ? C56 C57 1.372(10) . ? C56 H56 0.9300 . ? C57 C58 1.444(7) . ? C57 H57 0.9300 . ? C58 C59 1.363(8) . ? C59 C60 1.430(8) . ? C59 C65 1.507(6) . ? C60 C61 1.371(9) . ? C60 N64 1.430(8) . ? C61 C62 1.363(9) . ? C61 H61 0.9300 . ? C62 C63 1.409(9) . ? C62 H62 0.9300 . ? C63 N64 1.360(9) . ? C63 H63 0.9300 . ? C65 C66 1.367(9) . ? C65 C70 1.420(9) . ? C66 C67 1.410(9) . ? C66 H66 0.9300 . ? C67 C68 1.394(10) . ? C67 H67 0.9300 . ? C68 C69 1.386(10) . ? C68 H68 0.9300 . ? C69 C70 1.386(9) . ? C69 H69 0.9300 . ? C70 H70 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N12 Cu1 N29 96.8(2) . . ? N12 Cu1 N2 92.0(2) . . ? N29 Cu1 N2 146.62(15) . . ? N12 Cu1 N19 148.41(15) . . ? N29 Cu1 N19 92.0(2) . . ? N2 Cu1 N19 97.2(2) . . ? C3 N2 C6 107.3(5) . . ? C3 N2 Cu1 125.7(4) . . ? C6 N2 Cu1 126.8(4) . . ? N2 C3 C4 112.0(6) . . ? N2 C3 H3 124.0 . . ? C4 C3 H3 124.0 . . ? C3 C4 C5 106.8(6) . . ? C3 C4 H4 126.6 . . ? C5 C4 H4 126.6 . . ? C4 C5 C6 105.7(6) . . ? C4 C5 H5 127.1 . . ? C6 C5 H5 127.1 . . ? C7 C6 N2 125.5(6) . . ? C7 C6 C5 125.9(6) . . ? N2 C6 C5 108.2(6) . . ? C6 C7 C8 124.4(6) . . ? C6 C7 C13 118.6(5) . . ? C8 C7 C13 117.0(6) . . ? C9 C8 N12 110.0(6) . . ? C9 C8 C7 127.8(6) . . ? N12 C8 C7 122.2(6) . . ? C10 C9 C8 108.1(6) . . ? C10 C9 H9 126.0 . . ? C8 C9 H9 126.0 . . ? C9 C10 C11 106.5(5) . . ? C9 C10 H10 126.8 . . ? C11 C10 H10 126.8 . . ? N12 C11 C10 110.3(6) . . ? N12 C11 H11 124.8 . . ? C10 C11 H11 124.8 . . ? C8 N12 C11 105.1(6) . . ? C8 N12 Cu1 129.0(5) . . ? C11 N12 Cu1 125.5(5) . . ? C14 C13 C18 118.7(6) . . ? C14 C13 C7 121.9(6) . . ? C18 C13 C7 119.4(6) . . ? C13 C14 C15 122.3(6) . . ? C13 C14 H14 118.9 . . ? C15 C14 H14 118.9 . . ? C14 C15 C16 119.7(6) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 118.0(6) . . ? C17 C16 H16 121.0 . . ? C15 C16 H16 121.0 . . ? C18 C17 C16 122.6(6) . . ? C18 C17 H17 118.7 . . ? C16 C17 H17 118.7 . . ? C17 C18 C13 118.8(6) . . ? C17 C18 H18 120.6 . . ? C13 C18 H18 120.6 . . ? C20 N19 C23 108.5(5) . . ? C20 N19 Cu1 125.1(5) . . ? C23 N19 Cu1 126.3(4) . . ? N19 C20 C21 111.7(6) . . ? N19 C20 H20 124.1 . . ? C21 C20 H20 124.1 . . ? C22 C21 C20 106.0(5) . . ? C22 C21 H21 127.0 . . ? C20 C21 H21 127.0 . . ? C21 C22 C23 106.7(6) . . ? C21 C22 H22 126.7 . . ? C23 C22 H22 126.7 . . ? C24 C23 N19 125.9(6) . . ? C24 C23 C22 126.9(6) . . ? N19 C23 C22 107.1(6) . . ? C23 C24 C25 124.9(6) . . ? C23 C24 C30 118.7(5) . . ? C25 C24 C30 116.2(6) . . ? C26 C25 C24 128.3(6) . . ? C26 C25 N29 109.2(5) . . ? C24 C25 N29 122.4(6) . . ? C27 C26 C25 108.0(6) . . ? C27 C26 H26 126.0 . . ? C25 C26 H26 126.0 . . ? C26 C27 C28 105.3(6) . . ? C26 C27 H27 127.3 . . ? C28 C27 H27 127.3 . . ? N29 C28 C27 112.1(6) . . ? N29 C28 H28 123.9 . . ? C27 C28 H28 123.9 . . ? C28 N29 C25 105.2(6) . . ? C28 N29 Cu1 125.3(5) . . ? C25 N29 Cu1 128.1(4) . . ? C31 C30 C35 118.3(6) . . ? C31 C30 C24 122.9(6) . . ? C35 C30 C24 118.7(6) . . ? C30 C31 C32 122.7(6) . . ? C30 C31 H31 118.6 . . ? C32 C31 H31 118.6 . . ? C33 C32 C31 118.2(6) . . ? C33 C32 H32 120.9 . . ? C31 C32 H32 120.9 . . ? C32 C33 C34 121.3(6) . . ? C32 C33 H33 119.4 . . ? C34 C33 H33 119.4 . . ? C33 C34 C35 121.4(6) . . ? C33 C34 H34 119.3 . . ? C35 C34 H34 119.3 . . ? C34 C35 C30 118.1(6) . . ? C34 C35 H35 121.0 . . ? C30 C35 H35 121.0 . . ? N64 Cu36 N47 96.5(2) . . ? N64 Cu36 N37 147.4(3) . . ? N47 Cu36 N37 91.85(16) . . ? N64 Cu36 N54 92.35(16) . . ? N47 Cu36 N54 147.0(2) . . ? N37 Cu36 N54 97.6(2) . . ? C38 N37 C41 107.9(5) . . ? C38 N37 Cu36 125.5(5) . . ? C41 N37 Cu36 126.6(4) . . ? N37 C38 C39 111.6(6) . . ? N37 C38 H38 124.2 . . ? C39 C38 H38 124.2 . . ? C40 C39 C38 107.4(6) . . ? C40 C39 H39 126.3 . . ? C38 C39 H39 126.3 . . ? C39 C40 C41 105.6(6) . . ? C39 C40 H40 127.2 . . ? C41 C40 H40 127.2 . . ? C42 C41 N37 125.2(5) . . ? C42 C41 C40 126.8(6) . . ? N37 C41 C40 107.5(6) . . ? C41 C42 C43 125.5(4) . . ? C41 C42 C48 118.2(5) . . ? C43 C42 C48 116.2(6) . . ? C44 C43 N47 108.3(5) . . ? C44 C43 C42 129.5(6) . . ? N47 C43 C42 122.1(5) . . ? C45 C44 C43 109.0(6) . . ? C45 C44 H44 125.5 . . ? C43 C44 H44 125.5 . . ? C44 C45 C46 105.2(6) . . ? C44 C45 H45 127.4 . . ? C46 C45 H45 127.4 . . ? N47 C46 C45 111.7(6) . . ? N47 C46 H46 124.2 . . ? C45 C46 H46 124.2 . . ? C46 N47 C43 105.8(5) . . ? C46 N47 Cu36 125.2(5) . . ? C43 N47 Cu36 128.7(4) . . ? C49 C48 C53 118.9(4) . . ? C49 C48 C42 122.0(6) . . ? C53 C48 C42 119.1(6) . . ? C48 C49 C50 121.3(6) . . ? C48 C49 H49 119.4 . . ? C50 C49 H49 119.4 . . ? C51 C50 C49 119.6(6) . . ? C51 C50 H50 120.2 . . ? C49 C50 H50 120.2 . . ? C50 C51 C52 120.6(4) . . ? C50 C51 H51 119.7 . . ? C52 C51 H51 119.7 . . ? C51 C52 C53 120.2(6) . . ? C51 C52 H52 119.9 . . ? C53 C52 H52 119.9 . . ? C52 C53 C48 119.3(6) . . ? C52 C53 H53 120.3 . . ? C48 C53 H53 120.3 . . ? C55 N54 C58 108.9(5) . . ? C55 N54 Cu36 124.2(5) . . ? C58 N54 Cu36 125.8(4) . . ? N54 C55 C56 110.9(6) . . ? N54 C55 H55 124.6 . . ? C56 C55 H55 124.6 . . ? C57 C56 C55 106.5(6) . . ? C57 C56 H56 126.8 . . ? C55 C56 H56 126.8 . . ? C56 C57 C58 106.9(5) . . ? C56 C57 H57 126.6 . . ? C58 C57 H57 126.6 . . ? C59 C58 N54 126.2(5) . . ? C59 C58 C57 126.4(5) . . ? N54 C58 C57 106.8(5) . . ? C58 C59 C60 125.3(4) . . ? C58 C59 C65 119.3(6) . . ? C60 C59 C65 115.2(6) . . ? C61 C60 N64 109.2(5) . . ? C61 C60 C59 129.4(6) . . ? N64 C60 C59 121.4(6) . . ? C60 C61 C62 109.5(6) . . ? C60 C61 H61 125.2 . . ? C62 C61 H61 125.2 . . ? C61 C62 C63 105.4(6) . . ? C61 C62 H62 127.3 . . ? C63 C62 H62 127.3 . . ? N64 C63 C62 112.0(5) . . ? N64 C63 H63 124.0 . . ? C62 C63 H63 124.0 . . ? C63 N64 C60 103.8(5) . . ? C63 N64 Cu36 127.0(4) . . ? C60 N64 Cu36 128.2(4) . . ? C66 C65 C70 120.2(5) . . ? C66 C65 C59 121.2(6) . . ? C70 C65 C59 118.6(6) . . ? C65 C66 C67 120.6(6) . . ? C65 C66 H66 119.7 . . ? C67 C66 H66 119.7 . . ? C68 C67 C66 118.7(7) . . ? C68 C67 H67 120.6 . . ? C66 C67 H67 120.6 . . ? C69 C68 C67 121.0(5) . . ? C69 C68 H68 119.5 . . ? C67 C68 H68 119.5 . . ? C70 C69 C68 120.2(7) . . ? C70 C69 H69 119.9 . . ? C68 C69 H69 119.9 . . ? C69 C70 C65 119.3(7) . . ? C69 C70 H70 120.4 . . ? C65 C70 H70 120.4 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 71.30 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.745 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 909365' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_wim103 #TrackingRef 'web_deposit_cif_file_2_LucVanMeervelt_1352127472.wim103.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H38 Cu N4' _chemical_formula_sum 'C54 H38 Cu N4' _chemical_formula_weight 806.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 18.9299(5) _cell_length_b 10.5052(3) _cell_length_c 21.7918(6) _cell_angle_alpha 90.00 _cell_angle_beta 113.925(2) _cell_angle_gamma 90.00 _cell_volume 3961.22(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 17448 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 70.93 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1676 _exptl_absorpt_coefficient_mu 1.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.651 _exptl_absorpt_correction_T_max 0.716 _exptl_absorpt_process_details 'Bruker SADABS (SADABS, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'crossed Goebel mirrors' _diffrn_measurement_device_type 'SMART 6000' _diffrn_measurement_method 'omega and phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39036 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 70.93 _reflns_number_total 7546 _reflns_number_gt 6992 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (SMART, 1997)' _computing_cell_refinement 'Bruker SAINT (SAINT, 1997)' _computing_data_reduction 'Bruker SAINT (SAINT, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 1998)' _computing_publication_material 'PLATON (Spek, 1998)' _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^)+(0.0460P)^2^+2.1928P] 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 7546 _refine_ls_number_parameters 532 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0901 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Cu1 Cu 0.763858(11) 0.46150(2) 0.749377(10) 0.01493(8) Uani 1 1 d . . . N2 N 0.70332(7) 0.52532(11) 0.65882(6) 0.0151(2) Uani 1 1 d . . . C3 C 0.65767(8) 0.63008(14) 0.64297(7) 0.0171(3) Uani 1 1 d . . . C4 C 0.59878(9) 0.61844(15) 0.57782(7) 0.0205(3) Uani 1 1 d . . . H4 H 0.5590 0.6785 0.5556 0.025 Uiso 1 1 calc R . . C5 C 0.60978(9) 0.50382(15) 0.55255(7) 0.0200(3) Uani 1 1 d . . . H5 H 0.5792 0.4698 0.5095 0.024 Uiso 1 1 calc R . . C6 C 0.67550(8) 0.44581(14) 0.60289(7) 0.0169(3) Uani 1 1 d . . . C7 C 0.70854(8) 0.32797(14) 0.59888(7) 0.0180(3) Uani 1 1 d . . . C8 C 0.76375(9) 0.26127(14) 0.65251(7) 0.0184(3) Uani 1 1 d . . . C9 C 0.80415(9) 0.14853(15) 0.64917(8) 0.0231(3) Uani 1 1 d . . . H9 H 0.8007 0.1062 0.6095 0.028 Uiso 1 1 calc R . . C10 C 0.84877(9) 0.11301(15) 0.71374(8) 0.0230(3) Uani 1 1 d . . . H10 H 0.8825 0.0418 0.7274 0.028 Uiso 1 1 calc R . . C11 C 0.83513(8) 0.20265(14) 0.75658(8) 0.0184(3) Uani 1 1 d . . . N12 N 0.78571(7) 0.29359(11) 0.71992(6) 0.0163(2) Uani 1 1 d . . . C13 C 0.67176(9) 0.74139(14) 0.68725(7) 0.0187(3) Uani 1 1 d . . . C14 C 0.60992(10) 0.81791(16) 0.68426(9) 0.0273(3) Uani 1 1 d . . . H14 H 0.5587 0.7968 0.6541 0.033 Uiso 1 1 calc R . . C15 C 0.62303(12) 0.92459(17) 0.72512(11) 0.0367(4) Uani 1 1 d . . . H15 H 0.5807 0.9753 0.7233 0.044 Uiso 1 1 calc R . . C16 C 0.69759(13) 0.95754(17) 0.76851(10) 0.0367(4) Uani 1 1 d . . . H16 H 0.7063 1.0312 0.7959 0.044 Uiso 1 1 calc R . . C17 C 0.75907(11) 0.88313(16) 0.77183(9) 0.0287(4) Uani 1 1 d . . . H17 H 0.8102 0.9055 0.8016 0.034 Uiso 1 1 calc R . . C18 C 0.74639(9) 0.77554(15) 0.73170(8) 0.0217(3) Uani 1 1 d . . . H18 H 0.7890 0.7245 0.7345 0.026 Uiso 1 1 calc R . . C19 C 0.67950(9) 0.26961(15) 0.53033(8) 0.0211(3) Uani 1 1 d . . . C20 C 0.68542(9) 0.33678(16) 0.47737(8) 0.0238(3) Uani 1 1 d . . . H20 H 0.7099 0.4177 0.4855 0.029 Uiso 1 1 calc R . . C21 C 0.65576(10) 0.28641(19) 0.41287(8) 0.0296(4) Uani 1 1 d . . . H21 H 0.6605 0.3326 0.3773 0.035 Uiso 1 1 calc R . . C22 C 0.61941(10) 0.16939(19) 0.40035(9) 0.0335(4) Uani 1 1 d . . . H22 H 0.5986 0.1356 0.3561 0.040 Uiso 1 1 calc R . . C23 C 0.61342(11) 0.10150(18) 0.45251(10) 0.0352(4) Uani 1 1 d . . . H23 H 0.5885 0.0209 0.4439 0.042 Uiso 1 1 calc R . . C24 C 0.64370(10) 0.15061(17) 0.51760(9) 0.0286(4) Uani 1 1 d . . . H24 H 0.6399 0.1031 0.5532 0.034 Uiso 1 1 calc R . . C25 C 0.86477(8) 0.19514(14) 0.83012(8) 0.0185(3) Uani 1 1 d . . . C26 C 0.82441(9) 0.24660(14) 0.86583(8) 0.0206(3) Uani 1 1 d . . . H26 H 0.7761 0.2872 0.8421 0.025 Uiso 1 1 calc R . . C27 C 0.85405(9) 0.23904(16) 0.93527(8) 0.0244(3) Uani 1 1 d . . . H27 H 0.8265 0.2758 0.9589 0.029 Uiso 1 1 calc R . . C28 C 0.92396(10) 0.17771(17) 0.97037(8) 0.0278(4) Uani 1 1 d . . . H28 H 0.9445 0.1728 1.0180 0.033 Uiso 1 1 calc R . . C29 C 0.96369(9) 0.12359(17) 0.93555(9) 0.0284(4) Uani 1 1 d . . . H29 H 1.0111 0.0804 0.9594 0.034 Uiso 1 1 calc R . . C30 C 0.93469(9) 0.13212(15) 0.86616(8) 0.0237(3) Uani 1 1 d . . . H30 H 0.9624 0.0950 0.8429 0.028 Uiso 1 1 calc R . . N31 N 0.69255(7) 0.51095(12) 0.79013(6) 0.0160(2) Uani 1 1 d . . . C32 C 0.61436(8) 0.51263(14) 0.76027(7) 0.0178(3) Uani 1 1 d . . . C33 C 0.58482(9) 0.59884(15) 0.79399(8) 0.0218(3) Uani 1 1 d . . . H33 H 0.5320 0.6190 0.7821 0.026 Uiso 1 1 calc R . . C34 C 0.64689(9) 0.64766(15) 0.84697(8) 0.0213(3) Uani 1 1 d . . . H34 H 0.6452 0.7071 0.8792 0.026 Uiso 1 1 calc R . . C35 C 0.71433(9) 0.59251(14) 0.84462(7) 0.0174(3) Uani 1 1 d . . . C36 C 0.79076(9) 0.61615(14) 0.88972(7) 0.0176(3) Uani 1 1 d . . . C37 C 0.85778(8) 0.57722(14) 0.88239(7) 0.0165(3) Uani 1 1 d . . . C38 C 0.93491(9) 0.59111(15) 0.93073(7) 0.0193(3) Uani 1 1 d . . . H38 H 0.9508 0.6297 0.9737 0.023 Uiso 1 1 calc R . . C39 C 0.98227(9) 0.53839(14) 0.90378(8) 0.0198(3) Uani 1 1 d . . . H39 H 1.0370 0.5327 0.9247 0.024 Uiso 1 1 calc R . . C40 C 0.93377(8) 0.49392(14) 0.83860(7) 0.0167(3) Uani 1 1 d . . . N41 N 0.85883(7) 0.51667(11) 0.82558(6) 0.0154(2) Uani 1 1 d . . . C42 C 0.56899(9) 0.42853(16) 0.70451(7) 0.0201(3) Uani 1 1 d . . . C43 C 0.49455(9) 0.46476(17) 0.65999(8) 0.0263(4) Uani 1 1 d . . . H43 H 0.4739 0.5438 0.6661 0.032 Uiso 1 1 calc R . . C44 C 0.45095(10) 0.38612(19) 0.60717(9) 0.0329(4) Uani 1 1 d . . . H44 H 0.4003 0.4112 0.5776 0.040 Uiso 1 1 calc R . . C45 C 0.48038(11) 0.27173(19) 0.59705(8) 0.0336(4) Uani 1 1 d . . . H45 H 0.4508 0.2196 0.5598 0.040 Uiso 1 1 calc R . . C46 C 0.55357(10) 0.23296(18) 0.64154(8) 0.0293(4) Uani 1 1 d . . . H46 H 0.5737 0.1536 0.6352 0.035 Uiso 1 1 calc R . . C47 C 0.59733(9) 0.31043(16) 0.69536(8) 0.0229(3) Uani 1 1 d . . . H47 H 0.6468 0.2828 0.7261 0.028 Uiso 1 1 calc R . . C48 C 0.79921(8) 0.68980(15) 0.95116(7) 0.0201(3) Uani 1 1 d . . . C49 C 0.82662(9) 0.81413(16) 0.96076(8) 0.0239(3) Uani 1 1 d . . . H49 H 0.8458 0.8508 0.9307 0.029 Uiso 1 1 calc R . . C50 C 0.82586(10) 0.88511(17) 1.01467(9) 0.0284(4) Uani 1 1 d . . . H50 H 0.8440 0.9705 1.0208 0.034 Uiso 1 1 calc R . . C51 C 0.79893(10) 0.83236(18) 1.05923(8) 0.0306(4) Uani 1 1 d . . . H51 H 0.7977 0.8818 1.0953 0.037 Uiso 1 1 calc R . . C52 C 0.77367(10) 0.70713(19) 1.05115(8) 0.0316(4) Uani 1 1 d . . . H52 H 0.7566 0.6697 1.0824 0.038 Uiso 1 1 calc R . . C53 C 0.77342(10) 0.63631(17) 0.99700(8) 0.0268(3) Uani 1 1 d . . . H53 H 0.7555 0.5508 0.9912 0.032 Uiso 1 1 calc R . . C54 C 0.96086(8) 0.43404(14) 0.79117(8) 0.0174(3) Uani 1 1 d . . . C55 C 0.92280(9) 0.45074(14) 0.72163(8) 0.0195(3) Uani 1 1 d . . . H55 H 0.8784 0.5037 0.7039 0.023 Uiso 1 1 calc R . . C56 C 0.94945(10) 0.39043(15) 0.67845(8) 0.0251(3) Uani 1 1 d . . . H56 H 0.9228 0.4016 0.6313 0.030 Uiso 1 1 calc R . . C57 C 1.01486(10) 0.31380(16) 0.70376(9) 0.0280(4) Uani 1 1 d . . . H57 H 1.0329 0.2724 0.6741 0.034 Uiso 1 1 calc R . . C58 C 1.05347(9) 0.29831(15) 0.77246(9) 0.0264(3) Uani 1 1 d . . . H58 H 1.0983 0.2463 0.7899 0.032 Uiso 1 1 calc R . . C59 C 1.02731(9) 0.35796(15) 0.81606(8) 0.0216(3) Uani 1 1 d . . . H59 H 1.0547 0.3472 0.8631 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01427(12) 0.01678(12) 0.01388(12) -0.00082(7) 0.00584(9) 0.00294(7) N2 0.0164(6) 0.0160(6) 0.0148(6) 0.0000(4) 0.0083(5) 0.0000(4) C3 0.0173(7) 0.0188(7) 0.0189(7) 0.0039(6) 0.0111(6) 0.0009(5) C4 0.0184(7) 0.0235(8) 0.0202(7) 0.0043(6) 0.0083(6) 0.0031(6) C5 0.0183(7) 0.0256(8) 0.0162(7) 0.0005(6) 0.0069(6) -0.0021(6) C6 0.0182(7) 0.0200(7) 0.0144(6) -0.0004(5) 0.0088(6) -0.0027(5) C7 0.0179(7) 0.0198(7) 0.0191(7) -0.0023(6) 0.0103(6) -0.0045(6) C8 0.0209(7) 0.0164(7) 0.0205(7) -0.0027(6) 0.0111(6) -0.0023(6) C9 0.0282(8) 0.0189(7) 0.0265(8) -0.0037(6) 0.0155(7) 0.0002(6) C10 0.0256(8) 0.0172(7) 0.0300(8) 0.0016(6) 0.0151(7) 0.0048(6) C11 0.0173(7) 0.0161(7) 0.0242(7) 0.0023(6) 0.0108(6) 0.0004(5) N12 0.0169(6) 0.0146(6) 0.0181(6) -0.0003(5) 0.0080(5) 0.0002(5) C13 0.0249(8) 0.0156(7) 0.0199(7) 0.0047(6) 0.0136(6) 0.0020(6) C14 0.0290(8) 0.0228(8) 0.0356(9) 0.0034(7) 0.0188(7) 0.0053(7) C15 0.0482(11) 0.0227(8) 0.0526(12) -0.0002(8) 0.0341(10) 0.0084(8) C16 0.0587(13) 0.0189(8) 0.0439(11) -0.0079(7) 0.0326(10) -0.0051(8) C17 0.0395(9) 0.0211(8) 0.0286(8) -0.0023(7) 0.0168(8) -0.0085(7) C18 0.0269(8) 0.0172(7) 0.0246(7) 0.0025(6) 0.0140(7) -0.0004(6) C19 0.0193(7) 0.0234(8) 0.0212(7) -0.0053(6) 0.0089(6) 0.0010(6) C20 0.0211(7) 0.0301(8) 0.0220(7) -0.0040(6) 0.0105(6) -0.0002(6) C21 0.0266(8) 0.0426(10) 0.0212(8) -0.0035(7) 0.0115(7) 0.0059(7) C22 0.0293(9) 0.0434(10) 0.0250(8) -0.0154(8) 0.0081(7) 0.0053(8) C23 0.0343(9) 0.0292(9) 0.0394(10) -0.0160(8) 0.0121(8) -0.0046(7) C24 0.0316(9) 0.0254(8) 0.0295(9) -0.0071(7) 0.0130(7) -0.0023(7) C25 0.0186(7) 0.0137(7) 0.0237(7) 0.0028(6) 0.0091(6) -0.0017(5) C26 0.0189(7) 0.0187(7) 0.0243(7) 0.0042(6) 0.0089(6) 0.0000(6) C27 0.0253(8) 0.0256(8) 0.0234(8) 0.0018(6) 0.0111(7) -0.0035(6) C28 0.0266(8) 0.0308(9) 0.0216(8) 0.0076(7) 0.0052(7) -0.0060(7) C29 0.0194(7) 0.0282(9) 0.0333(9) 0.0123(7) 0.0061(7) 0.0023(6) C30 0.0208(7) 0.0196(7) 0.0316(8) 0.0064(6) 0.0117(7) 0.0025(6) N31 0.0155(6) 0.0185(6) 0.0152(6) 0.0028(5) 0.0075(5) 0.0016(5) C32 0.0167(7) 0.0207(7) 0.0183(7) 0.0062(6) 0.0096(6) 0.0014(6) C33 0.0184(7) 0.0245(8) 0.0261(8) 0.0057(6) 0.0128(6) 0.0045(6) C34 0.0237(8) 0.0215(7) 0.0237(7) 0.0008(6) 0.0148(6) 0.0036(6) C35 0.0210(7) 0.0171(7) 0.0176(7) 0.0017(5) 0.0113(6) 0.0021(6) C36 0.0218(7) 0.0152(7) 0.0173(7) 0.0010(5) 0.0096(6) 0.0007(5) C37 0.0195(7) 0.0150(7) 0.0158(7) 0.0002(5) 0.0080(6) 0.0000(5) C38 0.0204(7) 0.0209(7) 0.0161(7) 0.0006(6) 0.0069(6) -0.0011(6) C39 0.0168(7) 0.0225(7) 0.0189(7) 0.0016(6) 0.0058(6) -0.0001(6) C40 0.0175(7) 0.0153(7) 0.0188(7) 0.0034(6) 0.0088(6) 0.0008(5) N41 0.0168(6) 0.0152(6) 0.0152(6) 0.0003(4) 0.0075(5) 0.0011(5) C42 0.0180(7) 0.0278(8) 0.0170(7) 0.0045(6) 0.0097(6) -0.0035(6) C43 0.0197(8) 0.0336(9) 0.0249(8) 0.0097(7) 0.0083(7) -0.0025(6) C44 0.0224(8) 0.0467(11) 0.0237(8) 0.0131(8) 0.0032(7) -0.0120(7) C45 0.0346(9) 0.0459(11) 0.0197(8) -0.0005(7) 0.0103(7) -0.0234(8) C46 0.0333(9) 0.0334(9) 0.0277(8) -0.0045(7) 0.0190(7) -0.0133(7) C47 0.0198(7) 0.0290(8) 0.0225(7) 0.0000(6) 0.0111(6) -0.0053(6) C48 0.0179(7) 0.0234(8) 0.0198(7) -0.0030(6) 0.0085(6) 0.0025(6) C49 0.0218(7) 0.0258(8) 0.0249(8) -0.0038(6) 0.0104(6) -0.0003(6) C50 0.0252(8) 0.0260(8) 0.0313(9) -0.0108(7) 0.0086(7) 0.0010(7) C51 0.0268(8) 0.0400(10) 0.0240(8) -0.0131(7) 0.0094(7) 0.0065(7) C52 0.0334(9) 0.0441(10) 0.0226(8) -0.0039(7) 0.0169(7) 0.0008(8) C53 0.0318(9) 0.0283(8) 0.0237(8) -0.0034(7) 0.0148(7) -0.0018(7) C54 0.0185(7) 0.0142(7) 0.0229(7) -0.0002(6) 0.0119(6) -0.0026(5) C55 0.0208(7) 0.0170(7) 0.0234(7) 0.0004(6) 0.0117(6) -0.0019(5) C56 0.0334(9) 0.0227(8) 0.0255(8) -0.0034(6) 0.0184(7) -0.0062(7) C57 0.0370(9) 0.0201(8) 0.0404(9) -0.0060(7) 0.0294(8) -0.0040(7) C58 0.0250(8) 0.0173(7) 0.0454(10) 0.0012(7) 0.0231(8) 0.0014(6) C59 0.0200(7) 0.0190(7) 0.0293(8) 0.0039(6) 0.0134(6) 0.0006(6) _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 Cu1 N2 1.9552(12) . ? Cu1 N31 1.9630(12) . ? Cu1 N41 1.9759(12) . ? Cu1 N12 1.9774(12) . ? N2 C3 1.3546(19) . ? N2 C6 1.3928(19) . ? C3 C4 1.411(2) . ? C3 C13 1.470(2) . ? C4 C5 1.375(2) . ? C4 H4 0.9500 . ? C5 C6 1.420(2) . ? C5 H5 0.9500 . ? C6 C7 1.406(2) . ? C7 C8 1.399(2) . ? C7 C19 1.498(2) . ? C8 N12 1.3968(19) . ? C8 C9 1.427(2) . ? C9 C10 1.367(2) . ? C9 H9 0.9500 . ? C10 C11 1.421(2) . ? C10 H10 0.9500 . ? C11 N12 1.3490(19) . ? C11 C25 1.470(2) . ? C13 C18 1.397(2) . ? C13 C14 1.400(2) . ? C14 C15 1.390(3) . ? C14 H14 0.9500 . ? C15 C16 1.387(3) . ? C15 H15 0.9500 . ? C16 C17 1.379(3) . ? C16 H16 0.9500 . ? C17 C18 1.389(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.395(2) . ? C19 C20 1.395(2) . ? C20 C21 1.389(2) . ? C20 H20 0.9500 . ? C21 C22 1.381(3) . ? C21 H21 0.9500 . ? C22 C23 1.385(3) . ? C22 H22 0.9500 . ? C23 C24 1.396(2) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C30 1.401(2) . ? C25 C26 1.402(2) . ? C26 C27 1.386(2) . ? C26 H26 0.9500 . ? C27 C28 1.389(2) . ? C27 H27 0.9500 . ? C28 C29 1.388(3) . ? C28 H28 0.9500 . ? C29 C30 1.387(2) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? N31 C32 1.3540(19) . ? N31 C35 1.3846(19) . ? C32 C33 1.416(2) . ? C32 C42 1.466(2) . ? C33 C34 1.370(2) . ? C33 H33 0.9500 . ? C34 C35 1.422(2) . ? C34 H34 0.9500 . ? C35 C36 1.403(2) . ? C36 C37 1.402(2) . ? C36 C48 1.498(2) . ? C37 N41 1.3990(18) . ? C37 C38 1.420(2) . ? C38 C39 1.372(2) . ? C38 H38 0.9500 . ? C39 C40 1.422(2) . ? C39 H39 0.9500 . ? C40 N41 1.3504(19) . ? C40 C54 1.469(2) . ? C42 C47 1.398(2) . ? C42 C43 1.401(2) . ? C43 C44 1.385(3) . ? C43 H43 0.9500 . ? C44 C45 1.379(3) . ? C44 H44 0.9500 . ? C45 C46 1.391(3) . ? C45 H45 0.9500 . ? C46 C47 1.391(2) . ? C46 H46 0.9500 . ? C47 H47 0.9500 . ? C48 C49 1.390(2) . ? C48 C53 1.395(2) . ? C49 C50 1.397(2) . ? C49 H49 0.9500 . ? C50 C51 1.382(3) . ? C50 H50 0.9500 . ? C51 C52 1.386(3) . ? C51 H51 0.9500 . ? C52 C53 1.393(2) . ? C52 H52 0.9500 . ? C53 H53 0.9500 . ? C54 C55 1.400(2) . ? C54 C59 1.401(2) . ? C55 C56 1.388(2) . ? C55 H55 0.9500 . ? C56 C57 1.390(3) . ? C56 H56 0.9500 . ? C57 C58 1.384(3) . ? C57 H57 0.9500 . ? C58 C59 1.386(2) . ? C58 H58 0.9500 . ? C59 H59 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N31 97.86(5) . . ? N2 Cu1 N41 135.14(5) . . ? N31 Cu1 N41 95.76(5) . . ? N2 Cu1 N12 95.30(5) . . ? N31 Cu1 N12 130.98(5) . . ? N41 Cu1 N12 107.20(5) . . ? C3 N2 C6 106.76(12) . . ? C3 N2 Cu1 126.02(10) . . ? C6 N2 Cu1 122.44(10) . . ? N2 C3 C4 110.38(13) . . ? N2 C3 C13 123.48(13) . . ? C4 C3 C13 126.06(14) . . ? C5 C4 C3 107.03(13) . . ? C5 C4 H4 126.5 . . ? C3 C4 H4 126.5 . . ? C4 C5 C6 107.11(13) . . ? C4 C5 H5 126.4 . . ? C6 C5 H5 126.4 . . ? N2 C6 C7 124.24(13) . . ? N2 C6 C5 108.70(13) . . ? C7 C6 C5 127.06(14) . . ? C8 C7 C6 126.12(14) . . ? C8 C7 C19 118.40(14) . . ? C6 C7 C19 115.46(13) . . ? N12 C8 C7 124.03(13) . . ? N12 C8 C9 108.55(13) . . ? C7 C8 C9 127.37(14) . . ? C10 C9 C8 107.12(14) . . ? C10 C9 H9 126.4 . . ? C8 C9 H9 126.4 . . ? C9 C10 C11 107.10(14) . . ? C9 C10 H10 126.4 . . ? C11 C10 H10 126.4 . . ? N12 C11 C10 110.32(13) . . ? N12 C11 C25 123.38(13) . . ? C10 C11 C25 126.14(14) . . ? C11 N12 C8 106.85(12) . . ? C11 N12 Cu1 128.73(10) . . ? C8 N12 Cu1 123.10(10) . . ? C18 C13 C14 118.44(15) . . ? C18 C13 C3 121.50(14) . . ? C14 C13 C3 120.04(14) . . ? C15 C14 C13 120.31(17) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 120.40(17) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 119.87(16) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.09(17) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C13 120.89(15) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 119.6 . . ? C24 C19 C20 118.96(15) . . ? C24 C19 C7 121.14(15) . . ? C20 C19 C7 119.86(14) . . ? C21 C20 C19 120.60(16) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 120.23(17) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 119.76(16) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C22 C23 C24 120.49(17) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C19 C24 C23 119.96(17) . . ? C19 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C30 C25 C26 118.34(14) . . ? C30 C25 C11 119.51(14) . . ? C26 C25 C11 122.13(13) . . ? C27 C26 C25 120.90(14) . . ? C27 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? C26 C27 C28 120.07(16) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C29 C28 C27 119.67(15) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C30 C29 C28 120.46(15) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C29 C30 C25 120.53(15) . . ? C29 C30 H30 119.7 . . ? C25 C30 H30 119.7 . . ? C32 N31 C35 106.95(12) . . ? C32 N31 Cu1 127.18(10) . . ? C35 N31 Cu1 122.11(10) . . ? N31 C32 C33 110.09(13) . . ? N31 C32 C42 123.33(13) . . ? C33 C32 C42 126.42(14) . . ? C34 C33 C32 107.01(13) . . ? C34 C33 H33 126.5 . . ? C32 C33 H33 126.5 . . ? C33 C34 C35 107.04(14) . . ? C33 C34 H34 126.5 . . ? C35 C34 H34 126.5 . . ? N31 C35 C36 125.05(13) . . ? N31 C35 C34 108.88(13) . . ? C36 C35 C34 126.08(14) . . ? C37 C36 C35 126.32(13) . . ? C37 C36 C48 118.62(13) . . ? C35 C36 C48 115.06(13) . . ? N41 C37 C36 124.85(13) . . ? N41 C37 C38 108.91(12) . . ? C36 C37 C38 126.24(13) . . ? C39 C38 C37 107.14(13) . . ? C39 C38 H38 126.4 . . ? C37 C38 H38 126.4 . . ? C38 C39 C40 106.92(13) . . ? C38 C39 H39 126.5 . . ? C40 C39 H39 126.5 . . ? N41 C40 C39 110.46(13) . . ? N41 C40 C54 124.39(13) . . ? C39 C40 C54 125.14(13) . . ? C40 N41 C37 106.57(12) . . ? C40 N41 Cu1 130.16(10) . . ? C37 N41 Cu1 122.85(10) . . ? C47 C42 C43 118.61(15) . . ? C47 C42 C32 121.57(14) . . ? C43 C42 C32 119.80(15) . . ? C44 C43 C42 120.43(17) . . ? C44 C43 H43 119.8 . . ? C42 C43 H43 119.8 . . ? C45 C44 C43 120.62(16) . . ? C45 C44 H44 119.7 . . ? C43 C44 H44 119.7 . . ? C44 C45 C46 119.75(16) . . ? C44 C45 H45 120.1 . . ? C46 C45 H45 120.1 . . ? C45 C46 C47 120.02(18) . . ? C45 C46 H46 120.0 . . ? C47 C46 H46 120.0 . . ? C46 C47 C42 120.51(16) . . ? C46 C47 H47 119.7 . . ? C42 C47 H47 119.7 . . ? C49 C48 C53 119.24(14) . . ? C49 C48 C36 121.20(14) . . ? C53 C48 C36 119.37(14) . . ? C48 C49 C50 119.86(16) . . ? C48 C49 H49 120.1 . . ? C50 C49 H49 120.1 . . ? C51 C50 C49 120.62(16) . . ? C51 C50 H50 119.7 . . ? C49 C50 H50 119.7 . . ? C50 C51 C52 119.84(15) . . ? C50 C51 H51 120.1 . . ? C52 C51 H51 120.1 . . ? C51 C52 C53 119.79(16) . . ? C51 C52 H52 120.1 . . ? C53 C52 H52 120.1 . . ? C52 C53 C48 120.61(16) . . ? C52 C53 H53 119.7 . . ? C48 C53 H53 119.7 . . ? C55 C54 C59 118.53(14) . . ? C55 C54 C40 122.33(14) . . ? C59 C54 C40 119.14(14) . . ? C56 C55 C54 120.50(15) . . ? C56 C55 H55 119.7 . . ? C54 C55 H55 119.7 . . ? C55 C56 C57 120.37(16) . . ? C55 C56 H56 119.8 . . ? C57 C56 H56 119.8 . . ? C58 C57 C56 119.48(15) . . ? C58 C57 H57 120.3 . . ? C56 C57 H57 120.3 . . ? C57 C58 C59 120.64(15) . . ? C57 C58 H58 119.7 . . ? C59 C58 H58 119.7 . . ? C58 C59 C54 120.45(15) . . ? C58 C59 H59 119.8 . . ? C54 C59 H59 119.8 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 70.93 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.302 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 909366'