# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 # 1. SUBMISSION DETAILs _publ_contact_author_name 'Flores-Alamo, Marcos' _publ_contact_author_address ; Facultad de Qu\'imica Universidad Nacional Aut\'onoma de M\'exico M\'exico, D.F.04510 M\'exico ; _publ_contact_author_phone 52(5)6232524 _publ_contact_author_fax 52(5)6232521 _publ_contact_author_email mfa@unam.mx _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; Mexico D.F, 2011-10-26 Please consider this CIF submission for a possible publication in Dalton Trans. This file was checked using the last release of the check procedure of Acta Cryst. Thanks ; #=========================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_data_validation_number ? _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ? _journal_techeditor_code ? _iucr_compatibility_tag ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_paper_category ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=========================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Mechanistic insight on the catecholase activity of dinuclear copper complexes with distant metal centers ; _publ_section_title_footnote ; Alternative name for ? ; loop_ _publ_author_name _publ_author_address M.R.Mendoza-Quijano ; Facultad de Qu\'imica Universidad Nacional Aut\'onoma de M\'exico M\'exico, D.F.04510 M\'exico ; G.Ferrer-Sueta ; Facultad de Ciencias Universidad de la Rep\'ublica Igu\'a 4225, 11400 Montevideo, Uruguay ; M.Flores-Alamo ; Facultad de Qu\'imica Universidad Nacional Aut\'onoma de M\'exico M\'exico, D.F.04510 M\'exico ; N.Aliaga-Alcalde ; Universidad de Barcelona Mart\'i i Franques 1-11 Barcelona 08028, Espa\.na ; V.Gomez-Vidales ; Instituto de Qu\'imica Universidad Nacional Aut\'onoma de M\'exico M\'exico, D.F.04510 M\'exico ; V.Ugalde-Saldivar ; Facultad de Qu\'imica Universidad Nacional Aut\'onoma de M\'exico M\'exico, D.F.04510 M\'exico ; 'L. Gasque' ; Facultad de Qu\'imica Universidad Nacional Aut\'onoma de M\'exico M\'exico, D.F.04510 M\'exico ; #=========================================================================== #SUBMISSION INFORMATION # # For a journal send the form to the address specified by the journal # # For a private communication to the CCDC send the form to the address # deposit@ccdc.cam.ac.uk # # For up-to-date information on deposition procedures, check the website # http://www.ccdc.cam.ac.uk/ #------------------ SECTION 2. COMPOUND(S) DETAILS #------------------------# data_cu2diep3 _database_code_depnum_ccdc_archive 'CCDC 851114' _audit_creation_date 2010-12-06T16:15:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #--------------------------------------------------------------------------- # CHEMICAL INFORMATION # #--------------------------------------------------------------------------- _chemical_name_systematic ; \m-[2,8-dimethyl-5,11-bis(pyridin-2-ylethyl)-1,4,5,6,7,10,11,12- octahydroimidazo[4,5-h]imidazo[4,5-c]-[1,6]-diazecine] bis [diacuacopper(II)] perchlorate dihydrate ; _chemical_formula_moiety 'C26 H40 Cl2 Cu2 N8 O12, 2(Cl O4), 2(H2 O)' _chemical_formula_sum 'C26 H44 Cl4 Cu2 N8 O22' _chemical_formula_weight 1089.57 _chemical_compound_source 'synthesis as described' #--------------------------------------------------------------------------- # UNIT CELL INFORMATION # #--------------------------------------------------------------------------- _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' _space_group_IT_number 14 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5610(5) _cell_length_b 14.9935(7) _cell_length_c 13.4829(6) _cell_angle_alpha 90 _cell_angle_beta 101.280(4) _cell_angle_gamma 90 _cell_volume 2093.73(17) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3982 _cell_measurement_theta_min 4.2652 _cell_measurement_theta_max 67.9752 _cell_measurement_wavelength 0.71073 #--------------------------------------------------------------------------- # CRYSTAL INFORMATION # #--------------------------------------------------------------------------- _exptl_crystal_description prism _exptl_crystal_colour dark-blue _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.31 _exptl_crystal_density_diffrn 1.728 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1116 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 3 1 0 0.1976 0 -1 -3 0.2698 0 1 -1 0.2842 0 -1 1 0.2336 1 1 -1 0.305 -3 -1 0 0.1692 0 1 1 0.1735 -1 1 1 0.1542 1 0 -3 0.1607 1 -1 -1 0.1542 _exptl_special_details ; ? ; #--------------------------------------------------------------------------- # ABSORPTION CORRECTION # #--------------------------------------------------------------------------- _exptl_absorpt_coefficient_mu 4.426 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.184 _exptl_absorpt_correction_T_max 0.419 #--------------------------------------------------------------------------- # DATA COLLECTION # #--------------------------------------------------------------------------- _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 10.4685 _diffrn_orient_matrix_ub_11 0.0586915 _diffrn_orient_matrix_ub_12 -0.0808807 _diffrn_orient_matrix_ub_13 -0.0451191 _diffrn_orient_matrix_ub_21 -0.108235 _diffrn_orient_matrix_ub_22 0.0048283 _diffrn_orient_matrix_ub_23 -0.0947478 _diffrn_orient_matrix_ub_31 0.0835236 _diffrn_orient_matrix_ub_32 0.063221 _diffrn_orient_matrix_ub_33 -0.0504963 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_unetI/netI 0.0271 _diffrn_reflns_number 7795 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.27 _diffrn_reflns_theta_max 68.09 _diffrn_reflns_theta_full 68.09 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 3797 _reflns_number_gt 3273 _reflns_threshold_expression >2\s(I) #--------------------------------------------------------------------------- # COMPUTER PROGRAMS USED # #--------------------------------------------------------------------------- _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #--------------------------------------------------------------------------- # STRUCTURE SOLUTION #--------------------------------------------------------------------------- _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #--------------------------------------------------------------------------- # REFINEMENT INFORMATION # #--------------------------------------------------------------------------- _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^ > 2\s(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^)+(0.0578P)^2^+2.4434P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0023(2) _refine_ls_number_reflns 3797 _refine_ls_number_parameters 303 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.555 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.07 #--------------------------------------------------------------------------- # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #--------------------------------------------------------------------------- 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C7 C 0.9544(3) 0.4422(2) 0.2851(2) 0.0379(7) Uani 1 1 d . . . C2 C 0.8797(3) 0.3724(2) 0.2184(3) 0.0396(7) Uani 1 1 d . . . H2A H 0.8109 0.3501 0.2499 0.047 Uiso 1 1 calc R . . H2B H 0.9364 0.3229 0.2114 0.047 Uiso 1 1 calc R . . C6 C 0.8222(3) 0.4091(2) 0.1146(2) 0.0368(7) Uani 1 1 d . . . H6A H 0.888 0.4422 0.0891 0.044 Uiso 1 1 calc R . . H6B H 0.795 0.3598 0.0688 0.044 Uiso 1 1 calc R . . C12 C 0.7010(3) 0.5410(2) 0.0367(2) 0.0308(6) Uani 1 1 d . . . H12A H 0.6524 0.5909 0.0559 0.037 Uiso 1 1 calc R . . H12B H 0.7875 0.5621 0.0352 0.037 Uiso 1 1 calc R . . C5 C 0.5886(3) 0.4143(2) 0.0990(2) 0.0283(6) Uani 1 1 d . . . H5A H 0.5698 0.392 0.0302 0.034 Uiso 1 1 calc R . . H5B H 0.5982 0.3639 0.145 0.034 Uiso 1 1 calc R . . C4 C 0.4835(3) 0.47334(18) 0.1174(2) 0.0258(6) Uani 1 1 d . . . C3 C 0.3611(3) 0.4888(2) 0.0668(2) 0.0289(6) Uani 1 1 d . . . C1 C 0.4054(3) 0.5752(2) 0.2036(2) 0.0312(6) Uani 1 1 d . . . C13 C 0.3873(3) 0.6439(3) 0.2788(3) 0.0437(8) Uani 1 1 d . . . H13A H 0.3879 0.6159 0.343 0.066 Uiso 1 1 calc R . . H13C H 0.3062 0.6735 0.2565 0.066 Uiso 1 1 calc R . . H13B H 0.4561 0.6866 0.2857 0.066 Uiso 1 1 calc R . . C8 C 1.0874(3) 0.4362(3) 0.3175(3) 0.0512(9) Uani 1 1 d . . . H8 H 1.1323 0.3878 0.2986 0.061 Uiso 1 1 calc R . . C9 C 1.1520(4) 0.5021(3) 0.3777(3) 0.0591(11) Uani 1 1 d . . . H9 H 1.2411 0.4989 0.3992 0.071 Uiso 1 1 calc R . . C10 C 1.0850(4) 0.5724(3) 0.4058(3) 0.0576(10) Uani 1 1 d . . . H10 H 1.127 0.6166 0.4482 0.069 Uiso 1 1 calc R . . C11 C 0.9536(3) 0.5766(3) 0.3700(3) 0.0490(9) Uani 1 1 d . . . H11 H 0.908 0.6252 0.3876 0.059 Uiso 1 1 calc R . . Cl1 Cl 0.00424(8) 0.68949(6) 0.06755(7) 0.0476(2) Uani 1 1 d . . . Cl2 Cl 0.52428(9) 0.34626(6) 0.38594(7) 0.0508(3) Uani 1 1 d . . . Cu1 Cu 0.69998(4) 0.52788(3) 0.25849(3) 0.02991(17) Uani 1 1 d . . . N2 N 0.7093(2) 0.46873(16) 0.11628(18) 0.0281(5) Uani 1 1 d . . . N4 N 0.3136(2) 0.55256(19) 0.12352(19) 0.0328(6) Uani 1 1 d . . . N1 N 0.5112(2) 0.52793(16) 0.20105(17) 0.0279(5) Uani 1 1 d . . . N3 N 0.8887(2) 0.5125(2) 0.31008(19) 0.0373(6) Uani 1 1 d . . . O1 O -0.0665(3) 0.6901(3) -0.0335(3) 0.0884(11) Uani 1 1 d . . . O2 O 0.1208(3) 0.7379(2) 0.0762(3) 0.0833(11) Uani 1 1 d . . . O1W O 0.6753(2) 0.56005(18) 0.39794(18) 0.0442(6) Uani 1 1 d D . . O3 O 0.0352(3) 0.5995(2) 0.0943(3) 0.0694(8) Uani 1 1 d . . . O2W O 0.7293(3) 0.67441(17) 0.2277(2) 0.0510(6) Uani 1 1 d D . . O4 O -0.0743(4) 0.7263(3) 0.1314(3) 0.0973(14) Uani 1 1 d . . . O3W O 0.3341(4) 0.2653(3) 0.5625(3) 0.0775(10) Uani 1 1 d D . . O5 O 0.6332(3) 0.3605(2) 0.3418(2) 0.0688(9) Uani 1 1 d . . . O6 O 0.5301(5) 0.2654(3) 0.4384(3) 0.1042(15) Uani 1 1 d . . . O7 O 0.4151(4) 0.3409(3) 0.3023(4) 0.1097(15) Uani 1 1 d . . . O8 O 0.5048(4) 0.4199(2) 0.4462(3) 0.0867(12) Uani 1 1 d . . . H4N H 0.235(6) 0.575(4) 0.112(5) 0.104 Uiso 1 1 d . . . H1D H 0.633(6) 0.522(4) 0.424(5) 0.13 Uiso 1 1 d D . . H1E H 0.656(7) 0.6147(18) 0.400(6) 0.13 Uiso 1 1 d D . . H2D H 0.786(5) 0.690(5) 0.196(5) 0.13 Uiso 1 1 d D . . H2E H 0.698(6) 0.727(2) 0.228(6) 0.13 Uiso 1 1 d D . . H3D H 0.258(7) 0.241(5) 0.550(6) 0.13 Uiso 1 1 d . . . H3E H 0.378(6) 0.254(5) 0.515(4) 0.13 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C7 0.0324(16) 0.0459(19) 0.0326(16) 0.0115(14) -0.0002(13) 0.0046(14) C2 0.0312(15) 0.0426(18) 0.0432(18) 0.0047(14) 0.0032(13) 0.0107(14) C6 0.0289(15) 0.0448(18) 0.0363(16) -0.0029(14) 0.0052(12) 0.0103(13) C12 0.0250(14) 0.0362(16) 0.0297(14) 0.0033(12) 0.0012(11) -0.0036(12) C5 0.0287(14) 0.0282(14) 0.0265(13) 0.0011(11) 0.0016(11) 0.0008(11) C4 0.0274(14) 0.0267(14) 0.0233(13) 0.0027(11) 0.0050(11) -0.0002(11) C3 0.0237(13) 0.0353(16) 0.0279(14) 0.0053(12) 0.0056(11) -0.0029(11) C1 0.0294(14) 0.0378(16) 0.0275(14) 0.0027(12) 0.0080(11) 0.0004(12) C13 0.0425(18) 0.050(2) 0.0401(17) -0.0059(15) 0.0106(14) 0.0072(15) C8 0.0364(18) 0.057(2) 0.056(2) 0.0174(18) -0.0012(16) 0.0091(16) C9 0.0298(17) 0.080(3) 0.060(2) 0.021(2) -0.0103(16) -0.0042(19) C10 0.041(2) 0.073(3) 0.052(2) -0.002(2) -0.0084(17) -0.0142(19) C11 0.0396(18) 0.061(2) 0.0416(18) -0.0076(17) -0.0030(15) -0.0065(17) Cl1 0.0329(4) 0.0463(5) 0.0666(6) -0.0118(4) 0.0173(4) -0.0032(3) Cl2 0.0612(6) 0.0388(5) 0.0595(5) -0.0039(4) 0.0290(4) -0.0019(4) Cu1 0.0258(2) 0.0372(3) 0.0246(2) -0.00179(17) -0.00037(16) 0.00159(17) N2 0.0267(12) 0.0308(13) 0.0244(11) 0.0011(10) -0.0008(9) 0.0026(10) N4 0.0241(12) 0.0437(15) 0.0308(13) 0.0018(11) 0.0056(10) 0.0029(11) N1 0.0268(12) 0.0323(13) 0.0234(11) 0.0012(9) 0.0023(9) 0.0002(10) N3 0.0282(13) 0.0511(17) 0.0287(13) 0.0004(12) -0.0038(10) -0.0005(12) O1 0.063(2) 0.114(3) 0.082(2) 0.008(2) -0.0019(18) 0.016(2) O2 0.0599(19) 0.087(2) 0.112(3) -0.030(2) 0.0406(19) -0.0335(17) O1W 0.0455(13) 0.0561(15) 0.0301(11) -0.0046(11) 0.0052(10) -0.0081(11) O3 0.0506(16) 0.0597(18) 0.099(2) 0.0093(17) 0.0177(16) 0.0080(14) O2W 0.0529(15) 0.0383(14) 0.0660(17) 0.0059(12) 0.0218(13) 0.0017(11) O4 0.087(2) 0.083(2) 0.144(4) -0.045(2) 0.079(3) -0.0159(19) O3W 0.074(2) 0.076(2) 0.090(2) -0.0260(19) 0.0311(19) -0.0213(18) O5 0.0731(19) 0.0674(19) 0.079(2) 0.0146(16) 0.0472(17) 0.0143(15) O6 0.164(4) 0.066(2) 0.105(3) 0.028(2) 0.080(3) 0.021(2) O7 0.099(3) 0.099(3) 0.117(3) 0.014(3) -0.015(3) -0.037(2) O8 0.125(3) 0.0598(19) 0.098(3) -0.0214(18) 0.077(2) -0.0104(19) #--------------------------------------------------------------------------- # MOLECULAR GEOMETRY # #--------------------------------------------------------------------------- _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C7 N3 1.341(4) . ? C7 C8 1.389(5) . ? C7 C2 1.499(5) . ? C2 C6 1.516(4) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C6 N2 1.494(4) . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C12 C3 1.489(4) 3_665 ? C12 N2 1.516(4) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C5 C4 1.478(4) . ? C5 N2 1.493(4) . ? C5 H5A 0.97 . ? C5 H5B 0.97 . ? C4 C3 1.358(4) . ? C4 N1 1.378(4) . ? C3 N4 1.379(4) . ? C3 C12 1.489(4) 3_665 ? C1 N1 1.329(4) . ? C1 N4 1.346(4) . ? C1 C13 1.484(4) . ? C13 H13A 0.96 . ? C13 H13C 0.96 . ? C13 H13B 0.96 . ? C8 C9 1.374(6) . ? C8 H8 0.93 . ? C9 C10 1.363(7) . ? C9 H9 0.93 . ? C10 C11 1.378(5) . ? C10 H10 0.93 . ? C11 N3 1.352(4) . ? C11 H11 0.93 . ? Cl1 O2 1.414(3) . ? Cl1 O3 1.418(3) 1 ? Cl1 O3 1.418(3) . ? Cl1 O4 1.419(3) . ? Cl1 O1 1.420(4) . ? Cl2 O6 1.399(4) 1 ? Cl2 O6 1.399(4) . ? Cl2 O8 1.409(3) . ? Cl2 O5 1.411(3) . ? Cl2 O7 1.449(4) . ? Cu1 N3 1.992(3) . ? Cu1 N1 1.993(2) . ? Cu1 O1W 2.007(2) . ? Cu1 N2 2.132(2) . ? Cu1 O2W 2.268(3) . ? N4 H4N 0.88(6) . ? O1W H1D 0.84(6) . ? O1W H1E 0.85(6) . ? O2W H2D 0.84(6) . ? O2W H2E 0.85(6) . ? O3W H3D 0.86(7) . ? O3W H3E 0.88(6) . ? 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 N3 C7 C8 120.8(3) . . ? N3 C7 C2 117.5(3) . . ? C8 C7 C2 121.6(3) . . ? C7 C2 C6 111.7(3) . . ? C7 C2 H2A 109.3 . . ? C6 C2 H2A 109.3 . . ? C7 C2 H2B 109.3 . . ? C6 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N2 C6 C2 112.4(3) . . ? N2 C6 H6A 109.1 . . ? C2 C6 H6A 109.1 . . ? N2 C6 H6B 109.1 . . ? C2 C6 H6B 109.1 . . ? H6A C6 H6B 107.9 . . ? C3 C12 N2 113.7(2) 3_665 . ? C3 C12 H12A 108.8 3_665 . ? N2 C12 H12A 108.8 . . ? C3 C12 H12B 108.8 3_665 . ? N2 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C4 C5 N2 107.1(2) . . ? C4 C5 H5A 110.3 . . ? N2 C5 H5A 110.3 . . ? C4 C5 H5B 110.3 . . ? N2 C5 H5B 110.3 . . ? H5A C5 H5B 108.6 . . ? C3 C4 N1 109.8(3) . . ? C3 C4 C5 133.7(3) . . ? N1 C4 C5 116.5(2) . . ? C4 C3 N4 104.7(3) . . ? C4 C3 C12 128.4(3) . 3_665 ? N4 C3 C12 125.9(3) . 3_665 ? N1 C1 N4 108.8(3) . . ? N1 C1 C13 127.5(3) . . ? N4 C1 C13 123.6(3) . . ? C1 C13 H13A 109.5 . . ? C1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? C1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? H13C C13 H13B 109.5 . . ? C9 C8 C7 119.6(4) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C10 C9 C8 119.7(3) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 118.7(4) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? N3 C11 C10 122.3(4) . . ? N3 C11 H11 118.8 . . ? C10 C11 H11 118.8 . . ? O2 Cl1 O3 108.3(2) . 1 ? O2 Cl1 O3 108.3(2) . . ? O2 Cl1 O4 110.7(2) . . ? O3 Cl1 O4 110.4(2) 1 . ? O3 Cl1 O4 110.4(2) . . ? O2 Cl1 O1 111.2(3) . . ? O3 Cl1 O1 107.6(2) 1 . ? O3 Cl1 O1 107.6(2) . . ? O4 Cl1 O1 108.6(3) . . ? O6 Cl2 O8 112.6(2) 1 . ? O6 Cl2 O8 112.6(2) . . ? O6 Cl2 O5 112.7(2) 1 . ? O6 Cl2 O5 112.7(2) . . ? O8 Cl2 O5 110.3(2) . . ? O6 Cl2 O7 107.1(3) 1 . ? O6 Cl2 O7 107.1(3) . . ? O8 Cl2 O7 108.0(3) . . ? O5 Cl2 O7 105.7(3) . . ? N3 Cu1 N1 173.01(11) . . ? N3 Cu1 O1W 90.31(11) . . ? N1 Cu1 O1W 93.46(10) . . ? N3 Cu1 N2 92.67(10) . . ? N1 Cu1 N2 82.51(9) . . ? O1W Cu1 N2 168.45(10) . . ? N3 Cu1 O2W 90.74(11) . . ? N1 Cu1 O2W 95.19(10) . . ? O1W Cu1 O2W 89.20(11) . . ? N2 Cu1 O2W 101.90(10) . . ? C5 N2 C6 109.3(2) . . ? C5 N2 C12 110.5(2) . . ? C6 N2 C12 110.7(2) . . ? C5 N2 Cu1 100.32(17) . . ? C6 N2 Cu1 116.09(18) . . ? C12 N2 Cu1 109.43(18) . . ? C1 N4 C3 109.6(2) . . ? C1 N4 H4N 124(4) . . ? C3 N4 H4N 127(4) . . ? C1 N1 C4 107.0(2) . . ? C1 N1 Cu1 140.6(2) . . ? C4 N1 Cu1 110.73(18) . . ? C7 N3 C11 118.8(3) . . ? C7 N3 Cu1 122.3(2) . . ? C11 N3 Cu1 118.8(2) . . ? Cu1 O1W H1D 114(5) . . ? Cu1 O1W H1E 110(5) . . ? H1D O1W H1E 119(7) . . ? Cu1 O2W H2D 120(5) . . ? Cu1 O2W H2E 145(5) . . ? H2D O2W H2E 94(6) . . ? H3D O3W H3E 112(7) . . ? 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 N3 C7 C2 C6 64.3(4) . . . . ? C8 C7 C2 C6 -113.7(3) . . . . ? C7 C2 C6 N2 -73.9(3) . . . . ? N2 C5 C4 C3 134.3(3) . . . . ? N2 C5 C4 N1 -43.4(3) . . . . ? N1 C4 C3 N4 -1.6(3) . . . . ? C5 C4 C3 N4 -179.4(3) . . . . ? N1 C4 C3 C12 167.0(3) . . . 3_665 ? C5 C4 C3 C12 -10.8(5) . . . 3_665 ? N3 C7 C8 C9 1.4(5) . . . . ? C2 C7 C8 C9 179.4(3) . . . . ? C7 C8 C9 C10 0.6(6) . . . . ? C8 C9 C10 C11 -2.0(6) . . . . ? C9 C10 C11 N3 1.6(6) . . . . ? C4 C5 N2 C6 171.2(2) . . . . ? C4 C5 N2 C12 -66.7(3) . . . . ? C4 C5 N2 Cu1 48.7(2) . . . . ? C2 C6 N2 C5 -89.7(3) . . . . ? C2 C6 N2 C12 148.3(3) . . . . ? C2 C6 N2 Cu1 22.7(3) . . . . ? C3 C12 N2 C5 -39.9(3) 3_665 . . . ? C3 C12 N2 C6 81.3(3) 3_665 . . . ? C3 C12 N2 Cu1 -149.5(2) 3_665 . . . ? N3 Cu1 N2 C5 139.61(17) . . . . ? N1 Cu1 N2 C5 -35.32(16) . . . . ? O1W Cu1 N2 C5 34.8(6) . . . . ? O2W Cu1 N2 C5 -129.07(16) . . . . ? N3 Cu1 N2 C6 22.1(2) . . . . ? N1 Cu1 N2 C6 -152.9(2) . . . . ? O1W Cu1 N2 C6 -82.7(5) . . . . ? O2W Cu1 N2 C6 113.4(2) . . . . ? N3 Cu1 N2 C12 -104.13(18) . . . . ? N1 Cu1 N2 C12 80.95(18) . . . . ? O1W Cu1 N2 C12 151.1(5) . . . . ? O2W Cu1 N2 C12 -12.81(19) . . . . ? N1 C1 N4 C3 -0.2(3) . . . . ? C13 C1 N4 C3 178.5(3) . . . . ? C4 C3 N4 C1 1.1(3) . . . . ? C12 C3 N4 C1 -167.9(3) 3_665 . . . ? N4 C1 N1 C4 -0.8(3) . . . . ? C13 C1 N1 C4 -179.4(3) . . . . ? N4 C1 N1 Cu1 162.0(2) . . . . ? C13 C1 N1 Cu1 -16.6(5) . . . . ? C3 C4 N1 C1 1.5(3) . . . . ? C5 C4 N1 C1 179.7(2) . . . . ? C3 C4 N1 Cu1 -166.88(19) . . . . ? C5 C4 N1 Cu1 11.3(3) . . . . ? O1W Cu1 N1 C1 43.1(3) . . . . ? N2 Cu1 N1 C1 -147.8(3) . . . . ? O2W Cu1 N1 C1 -46.4(3) . . . . ? O1W Cu1 N1 C4 -154.50(19) . . . . ? N2 Cu1 N1 C4 14.63(19) . . . . ? O2W Cu1 N1 C4 115.99(19) . . . . ? C8 C7 N3 C11 -1.8(5) . . . . ? C2 C7 N3 C11 -179.9(3) . . . . ? C8 C7 N3 Cu1 176.1(3) . . . . ? C2 C7 N3 Cu1 -1.9(4) . . . . ? C10 C11 N3 C7 0.4(5) . . . . ? C10 C11 N3 Cu1 -177.7(3) . . . . ? O1W Cu1 N3 C7 134.3(3) . . . . ? N2 Cu1 N3 C7 -34.5(3) . . . . ? O2W Cu1 N3 C7 -136.5(3) . . . . ? O1W Cu1 N3 C11 -47.7(3) . . . . ? N2 Cu1 N3 C11 143.4(3) . . . . ? O2W Cu1 N3 C11 41.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4N O3 0.88(6) 2.10(6) 2.973(4) 168(6) 1 O3W H3E O6 0.87(2) 2.09(4) 2.905(5) 156(7) 1 O3W H3E O6 0.87(6) 2.09(4) 2.905(5) 156(7) 1 O1W H1E O3W 0.85(6) 1.87(3) 2.678(5) 160(7) 3_666 O2W H2D O4 0.84(6) 1.93(4) 2.765(4) 176(7) 1_655 O2W H2E O7 0.85(6) 2.08(3) 2.911(5) 165(7) 2_655 O3W H3D O1 0.86(7) 2.14(7) 2.997(5) 174(7) 2_545 # END of CIF