# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email harmon@cas.usf.edu _publ_contact_author_name 'Julie Harmon' loop_ _publ_author_name 'Julie Harmon' 'Shisi Liu' 'Ramakanth Ananthoji' 'Sungyub Han' 'Bernard Knudsen' 'Xiao Li' 'Lukasz Wojtas' 'Justin Massing' 'Carmen Valdez Gauthier' data_ctmof _database_code_depnum_ccdc_archive 'CCDC 815800' #TrackingRef '- jm30_pus.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Catena-(bis(mu2-4,4-trimethylenedipyridine)) copper(ii) dinitrate 1,2-dichlorobenzene methanol solvate ; _chemical_name_common ; Catena-(bis(mu2-4,4-trimethylenedipyridine)) copper(ii) dinitrate 1,2-dichlorobenzene methanol solvate ; _chemical_melting_point ? _chemical_formula_moiety '(CuC26H28N5O3 1+), (NO3 1-), C6H4Cl2, 1.75(CH3OH)' _chemical_formula_sum 'C33.75 H39 Cl2 Cu N6 O7.75' _chemical_formula_weight 787.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.369(7) _cell_length_b 12.645(9) _cell_length_c 14.307(9) _cell_angle_alpha 102.839(13) _cell_angle_beta 92.253(14) _cell_angle_gamma 102.395(11) _cell_volume 1779(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 668 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 18.2 _exptl_crystal_description polyhedra _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 817 _exptl_absorpt_coefficient_mu 0.823 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8527 _exptl_absorpt_correction_T_max 0.8527 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9227 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.1619 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.62 _reflns_number_total 6463 _reflns_number_gt 3545 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0800P)^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 6463 _refine_ls_number_parameters 474 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.1486 _refine_ls_R_factor_gt 0.0771 _refine_ls_wR_factor_ref 0.1930 _refine_ls_wR_factor_gt 0.1639 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.022 _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 Cu1 Cu 0.78531(8) 0.25472(6) 0.26826(5) 0.0226(2) Uani 1 1 d . . . N1 N 0.3340(5) -0.3068(4) 0.6327(3) 0.0213(12) Uani 1 1 d . . . C1 C 0.4651(6) -0.2649(5) 0.6472(4) 0.0260(15) Uani 1 1 d . . . H1 H 0.5007 -0.2161 0.7075 0.031 Uiso 1 1 calc R . . C2 C 0.5499(6) -0.2892(5) 0.5793(4) 0.0219(14) Uani 1 1 d . . . H2 H 0.6426 -0.2585 0.5929 0.026 Uiso 1 1 calc R . . C3 C 0.4997(6) -0.3594(5) 0.4896(4) 0.0202(14) Uani 1 1 d . . . C4 C 0.3650(6) -0.4038(5) 0.4752(4) 0.0210(14) Uani 1 1 d . . . H4 H 0.3268 -0.4535 0.4158 0.025 Uiso 1 1 calc R . . C5 C 0.2858(6) -0.3757(5) 0.5479(4) 0.0255(15) Uani 1 1 d . . . H5 H 0.1931 -0.4069 0.5369 0.031 Uiso 1 1 calc R . . C6 C 0.5902(6) -0.3805(5) 0.4124(4) 0.0273(15) Uani 1 1 d . . . H6A H 0.5385 -0.4336 0.3549 0.033 Uiso 1 1 calc R . . H6B H 0.6584 -0.4154 0.4350 0.033 Uiso 1 1 calc R . . C7 C 0.6585(6) -0.2743(5) 0.3841(4) 0.0239(14) Uani 1 1 d . . . H7A H 0.7090 -0.2204 0.4416 0.029 Uiso 1 1 calc R . . H7B H 0.7221 -0.2920 0.3365 0.029 Uiso 1 1 calc R . . C8 C 0.5593(7) -0.2216(6) 0.3414(4) 0.0306(16) Uani 1 1 d . . . H8A H 0.5167 -0.2725 0.2798 0.037 Uiso 1 1 calc R . . H8B H 0.4892 -0.2135 0.3857 0.037 Uiso 1 1 calc R . . C9 C 0.6193(6) -0.1093(5) 0.3232(4) 0.0239(14) Uani 1 1 d . . . C10 C 0.6150(6) -0.0926(5) 0.2309(4) 0.0251(15) Uani 1 1 d . . . H10 H 0.5765 -0.1522 0.1775 0.030 Uiso 1 1 calc R . . C11 C 0.6674(6) 0.0121(5) 0.2181(4) 0.0262(15) Uani 1 1 d . . . H11 H 0.6631 0.0228 0.1545 0.031 Uiso 1 1 calc R . . N2 N 0.7244(5) 0.1005(4) 0.2898(3) 0.0223(12) Uani 1 1 d . . . C12 C 0.7303(6) 0.0811(6) 0.3787(4) 0.0279(15) Uani 1 1 d . . . H12 H 0.7709 0.1413 0.4310 0.033 Uiso 1 1 calc R . . C13 C 0.6807(6) -0.0208(5) 0.3975(4) 0.0283(15) Uani 1 1 d . . . H13 H 0.6885 -0.0303 0.4614 0.034 Uiso 1 1 calc R . . N21 N 0.8036(5) 0.3950(4) 0.2211(3) 0.0211(12) Uani 1 1 d . . . C21 C 0.9193(6) 0.4446(5) 0.1903(4) 0.0251(15) Uani 1 1 d . . . H21 H 0.9969 0.4187 0.2006 0.030 Uiso 1 1 calc R . . C22 C 0.9274(7) 0.5293(5) 0.1455(4) 0.0300(16) Uani 1 1 d . . . H22 H 1.0100 0.5610 0.1252 0.036 Uiso 1 1 calc R . . C23 C 0.8165(7) 0.5708(5) 0.1286(4) 0.0288(16) Uani 1 1 d . . . C24 C 0.7012(6) 0.5217(5) 0.1627(4) 0.0262(15) Uani 1 1 d . . . H24 H 0.6229 0.5477 0.1552 0.031 Uiso 1 1 calc R . . C25 C 0.6991(6) 0.4378(5) 0.2064(4) 0.0236(14) Uani 1 1 d . . . H25 H 0.6177 0.4065 0.2284 0.028 Uiso 1 1 calc R . . C26 C 0.8241(7) 0.6636(5) 0.0781(4) 0.0317(16) Uani 1 1 d . . . H26A H 0.7335 0.6651 0.0546 0.038 Uiso 1 1 calc R . . H26B H 0.8755 0.6499 0.0216 0.038 Uiso 1 1 calc R . . C27 C 0.8888(7) 0.7750(5) 0.1442(4) 0.0282(16) Uani 1 1 d . . . H27A H 0.8348 0.7898 0.1991 0.034 Uiso 1 1 calc R . . H27B H 0.9774 0.7718 0.1702 0.034 Uiso 1 1 calc R . . C28 C 0.9039(8) 0.8696(6) 0.0941(4) 0.0388(18) Uani 1 1 d . . . H28A H 0.9482 0.9399 0.1405 0.047 Uiso 1 1 calc R . . H28B H 0.8148 0.8769 0.0730 0.047 Uiso 1 1 calc R . . C29 C 0.9837(8) 0.8531(5) 0.0074(4) 0.0338(18) Uani 1 1 d . . . C30 C 1.1101(7) 0.8345(6) 0.0149(4) 0.0368(18) Uani 1 1 d . . . H30 H 1.1520 0.8385 0.0763 0.044 Uiso 1 1 calc R . . C31 C 1.1739(7) 0.8107(6) -0.0647(4) 0.0322(17) Uani 1 1 d . . . H31 H 1.2600 0.7973 -0.0576 0.039 Uiso 1 1 calc R . . N22 N 1.1220(5) 0.8050(4) -0.1532(3) 0.0259(12) Uani 1 1 d . . . C32 C 1.0037(7) 0.8288(5) -0.1613(4) 0.0296(16) Uani 1 1 d . . . H32 H 0.9681 0.8311 -0.2228 0.036 Uiso 1 1 calc R . . C33 C 0.9313(7) 0.8502(5) -0.0837(4) 0.0316(16) Uani 1 1 d . . . H33 H 0.8452 0.8631 -0.0927 0.038 Uiso 1 1 calc R . . C41 C 0.3028(9) 0.3999(9) 0.2059(6) 0.075(3) Uani 1 1 d . . . H41A H 0.3975 0.4265 0.2274 0.090 Uiso 1 1 calc R . . H41B H 0.2906 0.3409 0.1467 0.090 Uiso 1 1 calc R . . H41C H 0.2558 0.3703 0.2561 0.090 Uiso 1 1 calc R . . O41 O 0.2526(10) 0.4872(9) 0.1885(7) 0.154(4) Uani 1 1 d . . . H41 H 0.3137 0.5305 0.1653 0.185 Uiso 1 1 d . . . Cl1 Cl 0.2984(2) 1.00568(19) 0.24017(15) 0.0622(6) Uani 1 1 d . . . Cl2 Cl 0.0782(2) 1.05664(18) 0.37608(12) 0.0573(6) Uani 1 1 d . . . C51 C 0.2120(7) 0.9050(7) 0.2931(5) 0.047(2) Uani 1 1 d . . . C52 C 0.2396(8) 0.8006(7) 0.2717(6) 0.051(2) Uani 1 1 d . . . H52 H 0.3039 0.7848 0.2285 0.061 Uiso 1 1 calc R . . C53 C 0.1738(9) 0.7211(8) 0.3133(6) 0.057(2) Uani 1 1 d . . . H53 H 0.1956 0.6503 0.3005 0.068 Uiso 1 1 calc R . . C54 C 0.0747(9) 0.7397(8) 0.3744(5) 0.060(2) Uani 1 1 d . . . H54 H 0.0290 0.6827 0.4026 0.072 Uiso 1 1 calc R . . C55 C 0.0451(8) 0.8452(8) 0.3928(5) 0.054(2) Uani 1 1 d . . . H55 H -0.0234 0.8598 0.4325 0.064 Uiso 1 1 calc R . . C56 C 0.1141(8) 0.9265(7) 0.3541(5) 0.044(2) Uani 1 1 d . . . N61 N 1.0522(6) 0.3568(6) 0.4034(4) 0.0353(14) Uani 1 1 d . . . O62 O 1.1490(5) 0.3474(5) 0.4483(5) 0.0732(19) Uani 1 1 d . . . O63 O 0.9559(4) 0.2737(4) 0.3731(3) 0.0339(11) Uani 1 1 d . . . O64 O 1.0436(5) 0.4491(5) 0.3906(3) 0.0561(15) Uani 1 1 d . . . N71 N 0.5583(13) 0.3563(11) -0.0351(9) 0.096(4) Uani 0.75 1 d PDU A . O71 O 0.5684(7) 0.4305(8) -0.0677(6) 0.073(3) Uani 0.75 1 d PDU . . O72 O 0.6365(12) 0.3011(10) -0.0641(7) 0.116(4) Uani 0.75 1 d PDU . . O73 O 0.4736(11) 0.3228(11) 0.0230(8) 0.134(4) Uani 0.75 1 d PDU . . N81 N 0.4777(17) 0.1869(14) 0.0501(10) 0.021(4) Uiso 0.25 1 d PD A 1 O81 O 0.5525(17) 0.2158(16) -0.0088(11) 0.039(5) Uiso 0.25 1 d PD A 1 O82 O 0.3659(18) 0.1573(18) 0.0174(13) 0.050(5) Uiso 0.25 1 d PD A 1 C91 C 0.455(2) 0.0794(16) 0.0407(9) 0.162(10) Uani 0.75 1 d PU B 2 H91A H 0.5153 0.0734 -0.0103 0.242 Uiso 0.75 1 calc PR B 2 H91B H 0.3728 0.0941 0.0160 0.242 Uiso 0.75 1 calc PR B 2 H91C H 0.4348 0.0095 0.0618 0.242 Uiso 0.75 1 calc PR B 2 O91 O 0.5183(5) 0.1713(4) 0.1226(3) 0.0484(14) Uani 1 1 d DU B 2 H91 H 0.5220 0.2324 0.1076 0.073 Uiso 0.75 1 calc PRD B 2 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 0.0307(5) 0.0174(5) 0.0223(4) 0.0067(3) 0.0119(3) 0.0075(4) N1 0.027(3) 0.018(3) 0.021(2) 0.007(2) 0.008(2) 0.007(2) C1 0.037(4) 0.028(4) 0.011(3) 0.001(3) 0.005(3) 0.009(3) C2 0.019(3) 0.019(4) 0.028(3) 0.009(3) 0.008(3) 0.001(3) C3 0.035(4) 0.011(3) 0.021(3) 0.010(2) 0.008(3) 0.011(3) C4 0.029(4) 0.018(4) 0.016(3) 0.004(2) 0.008(3) 0.005(3) C5 0.025(4) 0.018(4) 0.034(3) 0.008(3) 0.008(3) 0.004(3) C6 0.035(4) 0.024(4) 0.026(3) 0.006(3) 0.013(3) 0.011(3) C7 0.024(4) 0.023(4) 0.029(3) 0.010(3) 0.013(3) 0.008(3) C8 0.040(4) 0.025(4) 0.032(3) 0.015(3) 0.007(3) 0.009(3) C9 0.028(4) 0.018(4) 0.028(3) 0.007(3) 0.007(3) 0.007(3) C10 0.034(4) 0.019(4) 0.024(3) 0.007(3) 0.006(3) 0.006(3) C11 0.032(4) 0.027(4) 0.021(3) 0.009(3) 0.004(3) 0.006(3) N2 0.025(3) 0.016(3) 0.025(3) 0.002(2) 0.005(2) 0.005(2) C12 0.040(4) 0.027(4) 0.018(3) 0.005(3) 0.003(3) 0.009(3) C13 0.034(4) 0.028(4) 0.024(3) 0.011(3) 0.009(3) 0.004(3) N21 0.024(3) 0.017(3) 0.021(2) 0.001(2) 0.009(2) 0.005(2) C21 0.022(4) 0.028(4) 0.031(3) 0.014(3) 0.013(3) 0.008(3) C22 0.036(4) 0.026(4) 0.027(3) 0.004(3) 0.013(3) 0.006(3) C23 0.038(4) 0.027(4) 0.020(3) 0.005(3) 0.002(3) 0.005(3) C24 0.028(4) 0.022(4) 0.029(3) 0.006(3) 0.000(3) 0.007(3) C25 0.021(4) 0.022(4) 0.027(3) 0.006(3) 0.007(3) 0.003(3) C26 0.033(4) 0.031(4) 0.033(3) 0.018(3) 0.002(3) 0.002(3) C27 0.039(4) 0.018(4) 0.033(3) 0.012(3) 0.018(3) 0.008(3) C28 0.064(5) 0.020(4) 0.041(4) 0.013(3) 0.029(4) 0.019(4) C29 0.065(5) 0.014(4) 0.027(3) 0.012(3) 0.021(3) 0.010(4) C30 0.048(5) 0.033(5) 0.027(3) 0.006(3) 0.003(3) 0.005(4) C31 0.033(4) 0.034(4) 0.026(3) 0.003(3) 0.012(3) 0.000(3) N22 0.033(3) 0.021(3) 0.025(3) 0.008(2) 0.008(2) 0.007(3) C32 0.051(5) 0.016(4) 0.027(3) 0.009(3) 0.010(3) 0.014(3) C33 0.046(5) 0.020(4) 0.040(4) 0.015(3) 0.023(3) 0.020(3) C41 0.063(6) 0.088(8) 0.066(6) -0.005(5) 0.002(5) 0.027(6) O41 0.146(8) 0.170(10) 0.176(8) 0.039(8) 0.097(7) 0.089(8) Cl1 0.0516(14) 0.0550(15) 0.0659(13) -0.0038(11) 0.0086(10) -0.0001(11) Cl2 0.0730(15) 0.0612(15) 0.0426(10) -0.0007(10) 0.0055(10) 0.0393(12) C51 0.037(5) 0.046(5) 0.052(4) 0.002(4) -0.005(4) 0.009(4) C52 0.043(5) 0.043(6) 0.060(5) 0.003(4) -0.011(4) 0.011(4) C53 0.058(6) 0.057(6) 0.053(5) 0.007(4) -0.020(4) 0.023(5) C54 0.083(7) 0.053(6) 0.037(4) 0.012(4) -0.023(4) 0.004(5) C55 0.055(5) 0.077(7) 0.029(4) 0.011(4) 0.003(4) 0.015(5) C56 0.046(5) 0.046(5) 0.034(4) -0.005(4) -0.001(3) 0.016(4) N61 0.027(4) 0.041(4) 0.032(3) -0.001(3) 0.003(3) 0.007(3) O62 0.031(3) 0.044(4) 0.133(5) 0.010(4) -0.036(3) 0.005(3) O63 0.028(3) 0.036(3) 0.033(2) 0.001(2) 0.000(2) 0.005(2) O64 0.064(4) 0.037(4) 0.062(3) 0.023(3) -0.018(3) -0.009(3) N71 0.103(10) 0.107(11) 0.086(9) 0.029(7) 0.010(6) 0.032(8) O71 0.052(5) 0.107(8) 0.081(5) 0.070(5) 0.000(4) 0.015(5) O72 0.144(10) 0.112(9) 0.097(7) 0.004(6) 0.015(6) 0.062(7) O73 0.102(8) 0.177(12) 0.129(9) 0.076(8) 0.017(6) 0.004(8) C91 0.21(2) 0.163(19) 0.048(8) 0.009(8) -0.003(10) -0.068(16) O91 0.068(4) 0.045(4) 0.035(3) 0.010(2) 0.018(2) 0.019(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 Cu1 N21 2.008(5) . ? Cu1 N1 2.011(5) 2_656 ? Cu1 N2 2.012(5) . ? Cu1 N22 2.021(5) 2_765 ? Cu1 O63 2.210(4) . ? N1 C5 1.333(7) . ? N1 C1 1.338(8) . ? N1 Cu1 2.011(5) 2_656 ? C1 C2 1.365(7) . ? C1 H1 0.9500 . ? C2 C3 1.396(8) . ? C2 H2 0.9500 . ? C3 C4 1.378(8) . ? C3 C6 1.493(7) . ? C4 C5 1.382(7) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.525(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.516(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.507(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C13 1.379(8) . ? C9 C10 1.384(7) . ? C10 C11 1.374(8) . ? C10 H10 0.9500 . ? C11 N2 1.345(7) . ? C11 H11 0.9500 . ? N2 C12 1.349(7) . ? C12 C13 1.370(9) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? N21 C25 1.340(7) . ? N21 C21 1.367(7) . ? C21 C22 1.355(8) . ? C21 H21 0.9500 . ? C22 C23 1.396(9) . ? C22 H22 0.9500 . ? C23 C24 1.384(8) . ? C23 C26 1.500(8) . ? C24 C25 1.342(8) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.510(9) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.509(8) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.519(8) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C33 1.382(9) . ? C29 C30 1.384(10) . ? C30 C31 1.348(8) . ? C30 H30 0.9500 . ? C31 N22 1.337(7) . ? C31 H31 0.9500 . ? N22 C32 1.330(8) . ? N22 Cu1 2.021(5) 2_765 ? C32 C33 1.374(8) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C41 O41 1.381(12) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? O41 H41 0.8724 . ? Cl1 C51 1.728(8) . ? Cl2 C56 1.729(8) . ? C51 C52 1.381(10) . ? C51 C56 1.397(10) . ? C52 C53 1.354(11) . ? C52 H52 0.9500 . ? C53 C54 1.400(11) . ? C53 H53 0.9500 . ? C54 C55 1.403(11) . ? C54 H54 0.9500 . ? C55 C56 1.358(10) . ? C55 H55 0.9500 . ? N61 O62 1.212(7) . ? N61 O64 1.242(7) . ? N61 O63 1.266(7) . ? N71 O71 1.125(12) . ? N71 O72 1.207(12) . ? N71 O73 1.302(12) . ? O72 O81 1.606(19) . ? O73 O81 1.71(2) . ? O73 N81 1.853(19) . ? N81 O82 1.181(16) . ? N81 O81 1.229(15) . ? C91 O91 1.470(15) . ? C91 H91A 0.9800 . ? C91 H91B 0.9800 . ? C91 H91C 0.9800 . ? O91 H91 0.8400 . ? 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 N21 Cu1 N1 91.15(19) . 2_656 ? N21 Cu1 N2 164.72(19) . . ? N1 Cu1 N2 88.24(19) 2_656 . ? N21 Cu1 N22 87.32(19) . 2_765 ? N1 Cu1 N22 170.5(2) 2_656 2_765 ? N2 Cu1 N22 90.77(19) . 2_765 ? N21 Cu1 O63 109.13(19) . . ? N1 Cu1 O63 95.30(18) 2_656 . ? N2 Cu1 O63 86.12(19) . . ? N22 Cu1 O63 94.05(19) 2_765 . ? C5 N1 C1 117.7(5) . . ? C5 N1 Cu1 121.9(4) . 2_656 ? C1 N1 Cu1 120.2(4) . 2_656 ? N1 C1 C2 123.0(5) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 119.5(6) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 117.4(5) . . ? C4 C3 C6 122.4(5) . . ? C2 C3 C6 120.1(6) . . ? C3 C4 C5 119.5(5) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 122.8(6) . . ? N1 C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? C3 C6 C7 112.6(5) . . ? C3 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C3 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 111.6(5) . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C7 113.9(5) . . ? C9 C8 H8A 108.8 . . ? C7 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? C7 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C13 C9 C10 118.2(6) . . ? C13 C9 C8 121.2(5) . . ? C10 C9 C8 120.6(5) . . ? C11 C10 C9 118.6(6) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? N2 C11 C10 124.3(5) . . ? N2 C11 H11 117.8 . . ? C10 C11 H11 117.8 . . ? C11 N2 C12 115.8(5) . . ? C11 N2 Cu1 122.4(4) . . ? C12 N2 Cu1 121.6(4) . . ? N2 C12 C13 123.6(6) . . ? N2 C12 H12 118.2 . . ? C13 C12 H12 118.2 . . ? C12 C13 C9 119.5(5) . . ? C12 C13 H13 120.2 . . ? C9 C13 H13 120.2 . . ? C25 N21 C21 115.4(5) . . ? C25 N21 Cu1 122.0(4) . . ? C21 N21 Cu1 122.1(4) . . ? C22 C21 N21 122.5(6) . . ? C22 C21 H21 118.8 . . ? N21 C21 H21 118.8 . . ? C21 C22 C23 121.2(6) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C24 C23 C22 115.5(6) . . ? C24 C23 C26 122.8(6) . . ? C22 C23 C26 121.6(6) . . ? C25 C24 C23 120.6(6) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? N21 C25 C24 124.8(6) . . ? N21 C25 H25 117.6 . . ? C24 C25 H25 117.6 . . ? C23 C26 C27 111.4(5) . . ? C23 C26 H26A 109.4 . . ? C27 C26 H26A 109.4 . . ? C23 C26 H26B 109.4 . . ? C27 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? C28 C27 C26 112.7(5) . . ? C28 C27 H27A 109.1 . . ? C26 C27 H27A 109.1 . . ? C28 C27 H27B 109.1 . . ? C26 C27 H27B 109.1 . . ? H27A C27 H27B 107.8 . . ? C27 C28 C29 112.8(5) . . ? C27 C28 H28A 109.0 . . ? C29 C28 H28A 109.0 . . ? C27 C28 H28B 109.0 . . ? C29 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C33 C29 C30 116.7(5) . . ? C33 C29 C28 121.7(7) . . ? C30 C29 C28 121.6(6) . . ? C31 C30 C29 120.1(6) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? N22 C31 C30 123.3(7) . . ? N22 C31 H31 118.3 . . ? C30 C31 H31 118.3 . . ? C32 N22 C31 117.4(5) . . ? C32 N22 Cu1 122.9(4) . 2_765 ? C31 N22 Cu1 119.3(4) . 2_765 ? N22 C32 C33 122.3(6) . . ? N22 C32 H32 118.8 . . ? C33 C32 H32 118.8 . . ? C32 C33 C29 120.0(6) . . ? C32 C33 H33 120.0 . . ? C29 C33 H33 120.0 . . ? O41 C41 H41A 109.5 . . ? O41 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? O41 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C41 O41 H41 108.4 . . ? C52 C51 C56 120.1(8) . . ? C52 C51 Cl1 118.4(6) . . ? C56 C51 Cl1 121.5(6) . . ? C53 C52 C51 119.2(8) . . ? C53 C52 H52 120.4 . . ? C51 C52 H52 120.4 . . ? C52 C53 C54 122.1(8) . . ? C52 C53 H53 118.9 . . ? C54 C53 H53 118.9 . . ? C53 C54 C55 117.8(8) . . ? C53 C54 H54 121.1 . . ? C55 C54 H54 121.1 . . ? C56 C55 C54 120.2(8) . . ? C56 C55 H55 119.9 . . ? C54 C55 H55 119.9 . . ? C55 C56 C51 120.5(8) . . ? C55 C56 Cl2 120.6(6) . . ? C51 C56 Cl2 118.9(6) . . ? O62 N61 O64 120.4(6) . . ? O62 N61 O63 120.3(7) . . ? O64 N61 O63 119.2(6) . . ? N61 O63 Cu1 128.8(4) . . ? O71 N71 O72 111.3(14) . . ? O71 N71 O73 129.3(14) . . ? O72 N71 O73 119.4(14) . . ? N71 O72 O81 82.9(12) . . ? N71 O73 O81 76.0(10) . . ? N71 O73 N81 116.0(12) . . ? O82 N81 O81 112.1(17) . . ? O82 N81 O73 86.3(14) . . ? O81 N81 O73 63.9(11) . . ? N81 O81 O72 156.3(17) . . ? N81 O81 O73 76.0(12) . . ? O72 O81 O73 81.4(10) . . ? O91 C91 H91A 109.5 . . ? O91 C91 H91B 109.5 . . ? H91A C91 H91B 109.5 . . ? O91 C91 H91C 109.5 . . ? H91A C91 H91C 109.5 . . ? H91B C91 H91C 109.5 . . ? C91 O91 H91 109.5 . . ? 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 C5 N1 C1 C2 0.4(9) . . . . ? Cu1 N1 C1 C2 -173.9(4) 2_656 . . . ? N1 C1 C2 C3 1.0(9) . . . . ? C1 C2 C3 C4 -1.9(8) . . . . ? C1 C2 C3 C6 175.9(5) . . . . ? C2 C3 C4 C5 1.5(8) . . . . ? C6 C3 C4 C5 -176.2(5) . . . . ? C1 N1 C5 C4 -0.9(8) . . . . ? Cu1 N1 C5 C4 173.4(4) 2_656 . . . ? C3 C4 C5 N1 -0.2(9) . . . . ? C4 C3 C6 C7 117.1(6) . . . . ? C2 C3 C6 C7 -60.6(7) . . . . ? C3 C6 C7 C8 -63.2(7) . . . . ? C6 C7 C8 C9 173.0(5) . . . . ? C7 C8 C9 C13 -61.2(8) . . . . ? C7 C8 C9 C10 118.3(6) . . . . ? C13 C9 C10 C11 -2.4(9) . . . . ? C8 C9 C10 C11 178.1(6) . . . . ? C9 C10 C11 N2 0.6(9) . . . . ? C10 C11 N2 C12 1.0(9) . . . . ? C10 C11 N2 Cu1 -174.6(5) . . . . ? N21 Cu1 N2 C11 34.7(9) . . . . ? N1 Cu1 N2 C11 122.6(5) 2_656 . . . ? N22 Cu1 N2 C11 -47.9(5) 2_765 . . . ? O63 Cu1 N2 C11 -142.0(5) . . . . ? N21 Cu1 N2 C12 -140.7(6) . . . . ? N1 Cu1 N2 C12 -52.7(5) 2_656 . . . ? N22 Cu1 N2 C12 136.7(5) 2_765 . . . ? O63 Cu1 N2 C12 42.7(5) . . . . ? C11 N2 C12 C13 -0.8(9) . . . . ? Cu1 N2 C12 C13 174.8(5) . . . . ? N2 C12 C13 C9 -1.0(10) . . . . ? C10 C9 C13 C12 2.6(9) . . . . ? C8 C9 C13 C12 -177.9(6) . . . . ? N1 Cu1 N21 C25 -44.4(4) 2_656 . . . ? N2 Cu1 N21 C25 43.2(9) . . . . ? N22 Cu1 N21 C25 126.2(4) 2_765 . . . ? O63 Cu1 N21 C25 -140.4(4) . . . . ? N1 Cu1 N21 C21 144.3(4) 2_656 . . . ? N2 Cu1 N21 C21 -128.2(7) . . . . ? N22 Cu1 N21 C21 -45.1(4) 2_765 . . . ? O63 Cu1 N21 C21 48.3(4) . . . . ? C25 N21 C21 C22 -1.7(8) . . . . ? Cu1 N21 C21 C22 170.1(4) . . . . ? N21 C21 C22 C23 0.1(9) . . . . ? C21 C22 C23 C24 1.7(9) . . . . ? C21 C22 C23 C26 -179.3(5) . . . . ? C22 C23 C24 C25 -1.9(8) . . . . ? C26 C23 C24 C25 179.1(6) . . . . ? C21 N21 C25 C24 1.5(8) . . . . ? Cu1 N21 C25 C24 -170.3(4) . . . . ? C23 C24 C25 N21 0.3(9) . . . . ? C24 C23 C26 C27 102.0(7) . . . . ? C22 C23 C26 C27 -76.9(7) . . . . ? C23 C26 C27 C28 177.2(5) . . . . ? C26 C27 C28 C29 -57.7(8) . . . . ? C27 C28 C29 C33 121.5(7) . . . . ? C27 C28 C29 C30 -55.2(9) . . . . ? C33 C29 C30 C31 -2.5(10) . . . . ? C28 C29 C30 C31 174.4(6) . . . . ? C29 C30 C31 N22 0.9(10) . . . . ? C30 C31 N22 C32 2.9(10) . . . . ? C30 C31 N22 Cu1 -170.5(5) . . . 2_765 ? C31 N22 C32 C33 -4.9(9) . . . . ? Cu1 N22 C32 C33 168.2(5) 2_765 . . . ? N22 C32 C33 C29 3.3(10) . . . . ? C30 C29 C33 C32 0.6(9) . . . . ? C28 C29 C33 C32 -176.3(6) . . . . ? C56 C51 C52 C53 -2.2(11) . . . . ? Cl1 C51 C52 C53 179.4(6) . . . . ? C51 C52 C53 C54 2.5(11) . . . . ? C52 C53 C54 C55 -0.5(11) . . . . ? C53 C54 C55 C56 -1.8(11) . . . . ? C54 C55 C56 C51 2.2(11) . . . . ? C54 C55 C56 Cl2 179.9(6) . . . . ? C52 C51 C56 C55 -0.1(11) . . . . ? Cl1 C51 C56 C55 178.3(6) . . . . ? C52 C51 C56 Cl2 -177.9(6) . . . . ? Cl1 C51 C56 Cl2 0.5(9) . . . . ? O62 N61 O63 Cu1 -167.3(5) . . . . ? O64 N61 O63 Cu1 16.1(8) . . . . ? N21 Cu1 O63 N61 1.0(5) . . . . ? N1 Cu1 O63 N61 -92.1(5) 2_656 . . . ? N2 Cu1 O63 N61 -180.0(5) . . . . ? N22 Cu1 O63 N61 89.5(5) 2_765 . . . ? O71 N71 O72 O81 -171.3(13) . . . . ? O73 N71 O72 O81 5.9(15) . . . . ? O71 N71 O73 O81 171.0(17) . . . . ? O72 N71 O73 O81 -5.6(14) . . . . ? O71 N71 O73 N81 173.5(14) . . . . ? O72 N71 O73 N81 -3.1(18) . . . . ? N71 O73 N81 O82 -120.6(15) . . . . ? O81 O73 N81 O82 -116.8(17) . . . . ? N71 O73 N81 O81 -3.8(14) . . . . ? O82 N81 O81 O72 92(4) . . . . ? O73 N81 O81 O72 18(4) . . . . ? O82 N81 O81 O73 74.0(17) . . . . ? N71 O72 O81 N81 -22(4) . . . . ? N71 O72 O81 O73 -3.9(10) . . . . ? N71 O73 O81 N81 176.5(13) . . . . ? N71 O73 O81 O72 3.7(9) . . . . ? N81 O73 O81 O72 -172.8(15) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.62 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.724 _refine_diff_density_min -0.691 _refine_diff_density_rms 0.110