# Electronic Supplementary Material (ESI) for CrystEngComm # 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_compound-5 _database_code_depnum_ccdc_archive 'CCDC 838922' #TrackingRef '17722_web_deposit_cif_file_0_SergioMartinez-Vargas_1360785764.articleADG.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ; catena-(Diaqua-(mu-5-methoxy-isophtalato-O,O'')-bis- (N,N,N',N'-tetramethylethylen ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H39 Cu2 N4 O6, Cl O4' _chemical_formula_sum 'C21 H39 Cl Cu2 N4 O10' _chemical_formula_weight 670.09 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 13.4164(8) _cell_length_b 15.4139(9) _cell_length_c 15.0463(9) _cell_angle_alpha 90.00 _cell_angle_beta 112.9660(10) _cell_angle_gamma 90.00 _cell_volume 2864.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 6497 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 31.54 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 1.635 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.5310 _exptl_absorpt_correction_T_max 0.9047 _exptl_absorpt_process_details 'SHELXTL V 6.12 (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 291(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 AXS CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 0.83 _diffrn_reflns_number 23165 _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_sigmaI/netI 0.0707 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5055 _reflns_number_gt 3184 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 6.23A (Bruker, 1999)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0290P)^2^] 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 5055 _refine_ls_number_parameters 392 _refine_ls_number_restraints 161 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0743 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 0.821 _refine_ls_restrained_S_all 0.884 _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 0.06592(4) 0.19417(3) 0.02577(3) 0.03453(14) Uani 1 1 d . . . Cu2 Cu -0.00996(3) 0.30099(3) 0.17614(3) 0.03308(13) Uani 1 1 d . . . O5 O 0.1801(2) 0.29773(16) 0.07723(18) 0.0446(7) Uani 1 1 d . . . O6 O 0.1308(2) 0.37502(16) 0.17737(19) 0.0447(7) Uani 1 1 d . . . O7 O 0.3915(2) 0.61847(16) 0.35910(19) 0.0471(7) Uani 1 1 d . . . O8 O 0.4423(2) 0.69271(15) 0.25549(17) 0.0451(7) Uani 1 1 d . . . O9 O 0.5186(2) 0.43705(17) 0.08315(19) 0.0495(7) Uani 1 1 d . . . O10 O -0.0509(2) 0.24657(16) 0.05116(18) 0.0388(6) Uani 1 1 d D . . H10 H -0.094(2) 0.2080(18) 0.050(3) 0.047 Uiso 1 1 d D . . N1 N -0.0018(3) 0.2320(2) -0.1189(2) 0.0456(9) Uani 1 1 d . . . N2 N 0.1679(3) 0.1195(2) -0.0157(2) 0.0451(9) Uani 1 1 d . . . N3 N 0.0097(3) 0.3523(2) 0.3072(2) 0.0448(9) Uani 1 1 d . . . N4 N -0.1200(3) 0.4011(2) 0.1189(3) 0.0485(9) Uani 1 1 d . . . C1 C 0.2817(3) 0.4216(2) 0.1473(2) 0.0276(8) Uani 1 1 d . . . C2 C 0.3002(3) 0.4933(2) 0.2061(2) 0.0305(9) Uani 1 1 d . . . H2 H 0.2536 0.5055 0.2369 0.037 Uiso 1 1 calc R . . C3 C 0.3876(3) 0.5475(2) 0.2199(2) 0.0311(9) Uani 1 1 d . . . C4 C 0.4592(3) 0.5277(2) 0.1769(2) 0.0337(9) Uani 1 1 d . . . H4 H 0.5184 0.5635 0.1866 0.040 Uiso 1 1 calc R . . C5 C 0.4423(3) 0.4541(2) 0.1193(2) 0.0326(9) Uani 1 1 d . . . C6 C 0.3527(3) 0.4031(2) 0.1036(2) 0.0295(9) Uani 1 1 d . . . H6 H 0.3397 0.3553 0.0628 0.035 Uiso 1 1 calc R . . C7 C 0.1889(3) 0.3601(2) 0.1326(2) 0.0297(9) Uani 1 1 d . . . C8 C 0.4090(3) 0.6264(2) 0.2840(3) 0.0341(9) Uani 1 1 d . . . C9 C 0.4951(3) 0.3673(3) 0.0155(3) 0.0571(12) Uani 1 1 d . . . H9A H 0.4962 0.3135 0.0479 0.086 Uiso 1 1 calc R . . H9B H 0.5485 0.3658 -0.0123 0.086 Uiso 1 1 calc R . . H9C H 0.4248 0.3758 -0.0347 0.086 Uiso 1 1 calc R . . C10 C 0.1617(4) 0.1568(3) -0.1091(3) 0.0633(13) Uani 1 1 d . . . H10A H 0.2047 0.2094 -0.0972 0.076 Uiso 1 1 calc R . . H10B H 0.1909 0.1156 -0.1415 0.076 Uiso 1 1 calc R . . C11 C 0.0474(4) 0.1767(3) -0.1716(3) 0.0642(14) Uani 1 1 d . . . H11A H 0.0445 0.2065 -0.2293 0.077 Uiso 1 1 calc R . . H11B H 0.0067 0.1231 -0.1911 0.077 Uiso 1 1 calc R . . C12 C 0.1296(4) 0.0285(3) -0.0295(3) 0.0682(14) Uani 1 1 d . . . H12A H 0.0558 0.0266 -0.0751 0.102 Uiso 1 1 calc R . . H12B H 0.1341 0.0051 0.0311 0.102 Uiso 1 1 calc R . . H12C H 0.1740 -0.0052 -0.0533 0.102 Uiso 1 1 calc R . . C13 C 0.2811(4) 0.1211(3) 0.0540(3) 0.0653(14) Uani 1 1 d . . . H13A H 0.2852 0.0995 0.1151 0.098 Uiso 1 1 calc R . . H13B H 0.3077 0.1796 0.0616 0.098 Uiso 1 1 calc R . . H13C H 0.3243 0.0854 0.0307 0.098 Uiso 1 1 calc R . . C14 C -0.1204(4) 0.2233(3) -0.1622(3) 0.0742(15) Uani 1 1 d . . . H14A H -0.1467 0.2385 -0.2293 0.111 Uiso 1 1 calc R . . H14B H -0.1519 0.2613 -0.1297 0.111 Uiso 1 1 calc R . . H14C H -0.1401 0.1644 -0.1558 0.111 Uiso 1 1 calc R . . C15 C 0.0250(4) 0.3238(3) -0.1277(3) 0.0791(17) Uani 1 1 d . . . H15A H 0.1021 0.3303 -0.1046 0.119 Uiso 1 1 calc R . . H15B H -0.0024 0.3595 -0.0901 0.119 Uiso 1 1 calc R . . H15C H -0.0073 0.3412 -0.1942 0.119 Uiso 1 1 calc R . . C16 C -0.1280(5) 0.4476(3) 0.1999(4) 0.097(2) Uani 1 1 d . . . H16A H -0.1436 0.5082 0.1824 0.117 Uiso 1 1 calc R . . H16B H -0.1878 0.4242 0.2132 0.117 Uiso 1 1 calc R . . C17 C -0.0306(4) 0.4419(3) 0.2858(4) 0.0844(17) Uani 1 1 d . . . H17A H -0.0446 0.4645 0.3400 0.101 Uiso 1 1 calc R . . H17B H 0.0249 0.4777 0.2780 0.101 Uiso 1 1 calc R . . C18 C -0.2275(4) 0.3716(3) 0.0533(4) 0.107(2) Uani 1 1 d . . . H18A H -0.2568 0.3331 0.0872 0.160 Uiso 1 1 calc R . . H18B H -0.2217 0.3415 -0.0003 0.160 Uiso 1 1 calc R . . H18C H -0.2745 0.4207 0.0302 0.160 Uiso 1 1 calc R . . C19 C -0.0812(4) 0.4577(3) 0.0610(3) 0.0698(15) Uani 1 1 d . . . H19A H -0.1321 0.5039 0.0341 0.105 Uiso 1 1 calc R . . H19B H -0.0738 0.4248 0.0097 0.105 Uiso 1 1 calc R . . H19C H -0.0122 0.4817 0.1012 0.105 Uiso 1 1 calc R . . C20 C 0.1231(4) 0.3553(3) 0.3754(3) 0.0733(15) Uani 1 1 d . . . H20A H 0.1279 0.3844 0.4333 0.110 Uiso 1 1 calc R . . H20B H 0.1652 0.3861 0.3467 0.110 Uiso 1 1 calc R . . H20C H 0.1504 0.2972 0.3907 0.110 Uiso 1 1 calc R . . C21 C -0.0521(4) 0.3018(3) 0.3506(4) 0.0875(17) Uani 1 1 d . . . H21A H -0.0219 0.2447 0.3658 0.131 Uiso 1 1 calc R . . H21B H -0.1262 0.2978 0.3059 0.131 Uiso 1 1 calc R . . H21C H -0.0490 0.3300 0.4086 0.131 Uiso 1 1 calc R . . Cl1 Cl 0.71628(12) 0.13963(9) 0.17601(10) 0.0749(4) Uani 1 1 d DU . . O1 O 0.7521(9) 0.1518(7) 0.2749(4) 0.124(3) Uani 0.550(8) 1 d PDU A 1 O2 O 0.7192(9) 0.0498(3) 0.1576(7) 0.115(3) Uani 0.550(8) 1 d PDU A 1 O3 O 0.6079(5) 0.1639(8) 0.1344(7) 0.158(4) Uani 0.550(8) 1 d PDU A 1 O4 O 0.7775(9) 0.1847(7) 0.1370(9) 0.142(4) Uani 0.550(8) 1 d PDU A 1 O1A O 0.7677(9) 0.1048(8) 0.2671(6) 0.135(5) Uani 0.450(8) 1 d PDU A 2 O2A O 0.6389(10) 0.0865(8) 0.1148(6) 0.140(4) Uani 0.450(8) 1 d PDU A 2 O3A O 0.6709(10) 0.2193(5) 0.1853(9) 0.131(4) Uani 0.450(8) 1 d PDU A 2 O4A O 0.7961(9) 0.1585(7) 0.1386(10) 0.098(3) Uani 0.450(8) 1 d PDU A 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 0.0421(3) 0.0288(3) 0.0323(3) -0.0011(2) 0.0141(2) -0.0058(2) Cu2 0.0355(3) 0.0249(3) 0.0412(3) 0.0052(2) 0.0175(2) 0.0045(2) O5 0.0473(17) 0.0412(16) 0.0518(17) -0.0205(14) 0.0262(14) -0.0208(14) O6 0.0414(17) 0.0440(17) 0.0592(19) -0.0129(14) 0.0312(15) -0.0127(13) O7 0.067(2) 0.0394(17) 0.0455(18) -0.0150(14) 0.0338(16) -0.0176(14) O8 0.0695(19) 0.0260(14) 0.0417(16) -0.0064(13) 0.0237(14) -0.0165(14) O9 0.0474(18) 0.0512(18) 0.063(2) -0.0221(15) 0.0362(15) -0.0171(14) O10 0.0373(17) 0.0358(17) 0.0412(16) 0.0035(13) 0.0130(13) -0.0023(12) N1 0.058(2) 0.040(2) 0.032(2) -0.0016(16) 0.0105(17) -0.0093(17) N2 0.053(2) 0.044(2) 0.042(2) -0.0056(17) 0.0229(18) -0.0047(17) N3 0.052(2) 0.039(2) 0.050(2) -0.0014(17) 0.0263(19) 0.0081(17) N4 0.043(2) 0.035(2) 0.070(3) 0.0147(19) 0.0242(19) 0.0113(17) C1 0.028(2) 0.025(2) 0.027(2) 0.0011(16) 0.0071(17) -0.0027(16) C2 0.035(2) 0.029(2) 0.030(2) -0.0019(17) 0.0161(18) -0.0012(17) C3 0.039(2) 0.023(2) 0.029(2) -0.0006(16) 0.0105(18) -0.0032(17) C4 0.040(2) 0.032(2) 0.030(2) -0.0007(17) 0.0152(19) -0.0129(17) C5 0.035(2) 0.032(2) 0.033(2) -0.0008(17) 0.0154(19) -0.0017(18) C6 0.033(2) 0.026(2) 0.026(2) -0.0051(16) 0.0084(17) -0.0032(17) C7 0.029(2) 0.029(2) 0.028(2) 0.0026(17) 0.0072(18) -0.0004(16) C8 0.034(2) 0.030(2) 0.036(2) -0.0055(18) 0.0118(19) -0.0046(17) C9 0.058(3) 0.062(3) 0.067(3) -0.023(2) 0.042(3) -0.008(2) C10 0.083(4) 0.066(3) 0.057(3) -0.010(3) 0.045(3) -0.009(3) C11 0.090(4) 0.063(3) 0.040(3) -0.006(2) 0.026(3) -0.012(3) C12 0.098(4) 0.039(3) 0.086(4) -0.018(3) 0.056(3) -0.008(3) C13 0.065(4) 0.074(4) 0.064(3) 0.000(3) 0.033(3) 0.012(3) C14 0.062(4) 0.094(4) 0.045(3) -0.010(3) -0.002(2) -0.005(3) C15 0.121(5) 0.051(3) 0.053(3) 0.011(2) 0.021(3) -0.018(3) C16 0.143(6) 0.073(4) 0.094(5) 0.023(3) 0.066(4) 0.071(4) C17 0.115(5) 0.051(3) 0.088(4) -0.016(3) 0.040(4) 0.030(3) C18 0.041(3) 0.071(4) 0.178(6) 0.043(4) 0.011(4) 0.013(3) C19 0.082(4) 0.045(3) 0.079(4) 0.031(3) 0.028(3) 0.014(3) C20 0.082(4) 0.088(4) 0.046(3) -0.018(3) 0.021(3) 0.001(3) C21 0.126(5) 0.088(4) 0.085(4) -0.010(3) 0.081(4) -0.021(4) Cl1 0.0811(10) 0.0697(9) 0.0777(10) 0.0140(7) 0.0351(8) -0.0135(7) O1 0.163(7) 0.121(8) 0.080(4) -0.018(4) 0.038(4) -0.054(7) O2 0.160(8) 0.064(3) 0.174(8) -0.009(4) 0.121(6) -0.015(4) O3 0.107(4) 0.154(9) 0.173(7) 0.004(7) 0.011(5) 0.041(5) O4 0.202(7) 0.097(7) 0.152(7) 0.034(6) 0.097(6) -0.051(7) O1A 0.130(8) 0.129(9) 0.112(6) 0.075(6) 0.010(5) -0.049(7) O2A 0.136(8) 0.146(8) 0.116(6) 0.014(6) 0.027(6) -0.085(7) O3A 0.112(8) 0.134(6) 0.171(9) 0.012(6) 0.083(7) 0.042(6) O4A 0.124(6) 0.067(7) 0.150(7) -0.002(5) 0.104(6) -0.012(5) _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 O10 1.930(3) . ? Cu1 O7 1.979(2) 2_545 ? Cu1 N2 2.062(3) . ? Cu1 N1 2.088(3) . ? Cu1 O5 2.138(2) . ? Cu2 O10 1.933(3) . ? Cu2 O8 1.985(2) 2_545 ? Cu2 N3 2.045(3) . ? Cu2 N4 2.075(3) . ? Cu2 O6 2.200(2) . ? O5 C7 1.247(4) . ? O6 C7 1.235(4) . ? O7 C8 1.247(4) . ? O7 Cu1 1.979(2) 2 ? O8 C8 1.256(4) . ? O8 Cu2 1.985(2) 2 ? O9 C5 1.359(4) . ? O9 C9 1.429(4) . ? O10 H10 0.829(11) . ? N1 C14 1.471(5) . ? N1 C15 1.480(5) . ? N1 C11 1.484(5) . ? N2 C13 1.470(5) . ? N2 C12 1.481(4) . ? N2 C10 1.490(5) . ? N3 C21 1.464(5) . ? N3 C20 1.466(5) . ? N3 C17 1.472(5) . ? N4 C16 1.454(5) . ? N4 C19 1.466(5) . ? N4 C18 1.467(5) . ? C1 C2 1.377(4) . ? C1 C6 1.381(5) . ? C1 C7 1.511(5) . ? C2 C3 1.388(4) . ? C2 H2 0.9300 . ? C3 C4 1.386(5) . ? C3 C8 1.508(5) . ? C4 C5 1.392(5) . ? C4 H4 0.9300 . ? C5 C6 1.378(4) . ? C6 H6 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.485(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.438(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? Cl1 O2A 1.360(5) . ? Cl1 O4 1.371(5) . ? Cl1 O1A 1.381(6) . ? Cl1 O1 1.387(5) . ? Cl1 O3 1.392(5) . ? Cl1 O3A 1.402(6) . ? Cl1 O2 1.416(5) . ? Cl1 O4A 1.421(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 O10 Cu1 O7 93.04(11) . 2_545 ? O10 Cu1 N2 168.48(12) . . ? O7 Cu1 N2 86.37(12) 2_545 . ? O10 Cu1 N1 91.87(12) . . ? O7 Cu1 N1 159.49(12) 2_545 . ? N2 Cu1 N1 84.89(13) . . ? O10 Cu1 O5 97.96(10) . . ? O7 Cu1 O5 101.64(11) 2_545 . ? N2 Cu1 O5 93.42(11) . . ? N1 Cu1 O5 97.37(11) . . ? O10 Cu2 O8 92.19(10) . 2_545 ? O10 Cu2 N3 170.87(12) . . ? O8 Cu2 N3 87.97(11) 2_545 . ? O10 Cu2 N4 91.88(13) . . ? O8 Cu2 N4 161.34(12) 2_545 . ? N3 Cu2 N4 85.17(13) . . ? O10 Cu2 O6 98.66(10) . . ? O8 Cu2 O6 102.38(10) 2_545 . ? N3 Cu2 O6 90.21(12) . . ? N4 Cu2 O6 95.00(11) . . ? C7 O5 Cu1 133.3(2) . . ? C7 O6 Cu2 128.4(2) . . ? C8 O7 Cu1 130.1(2) . 2 ? C8 O8 Cu2 131.2(2) . 2 ? C5 O9 C9 116.1(3) . . ? Cu1 O10 Cu2 115.45(12) . . ? Cu1 O10 H10 108(3) . . ? Cu2 O10 H10 105(3) . . ? C14 N1 C15 107.8(3) . . ? C14 N1 C11 110.0(3) . . ? C15 N1 C11 109.1(3) . . ? C14 N1 Cu1 113.1(3) . . ? C15 N1 Cu1 109.8(2) . . ? C11 N1 Cu1 107.1(3) . . ? C13 N2 C12 108.7(3) . . ? C13 N2 C10 109.1(3) . . ? C12 N2 C10 110.1(3) . . ? C13 N2 Cu1 113.5(2) . . ? C12 N2 Cu1 109.6(3) . . ? C10 N2 Cu1 105.7(2) . . ? C21 N3 C20 108.6(4) . . ? C21 N3 C17 111.9(4) . . ? C20 N3 C17 108.4(4) . . ? C21 N3 Cu2 110.0(3) . . ? C20 N3 Cu2 113.3(3) . . ? C17 N3 Cu2 104.7(3) . . ? C16 N4 C19 111.3(4) . . ? C16 N4 C18 110.0(4) . . ? C19 N4 C18 105.6(4) . . ? C16 N4 Cu2 107.0(3) . . ? C19 N4 Cu2 109.2(2) . . ? C18 N4 Cu2 113.7(3) . . ? C2 C1 C6 119.2(3) . . ? C2 C1 C7 121.9(3) . . ? C6 C1 C7 118.9(3) . . ? C1 C2 C3 120.6(3) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 119.8(3) . . ? C4 C3 C8 118.8(3) . . ? C2 C3 C8 121.3(3) . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? O9 C5 C6 124.3(3) . . ? O9 C5 C4 116.3(3) . . ? C6 C5 C4 119.4(3) . . ? C5 C6 C1 121.2(3) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? O6 C7 O5 126.3(3) . . ? O6 C7 C1 117.6(3) . . ? O5 C7 C1 116.0(3) . . ? O7 C8 O8 127.4(3) . . ? O7 C8 C3 116.4(3) . . ? O8 C8 C3 116.3(3) . . ? O9 C9 H9A 109.5 . . ? O9 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O9 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 N2 109.9(4) . . ? C11 C10 H10A 109.7 . . ? N2 C10 H10A 109.7 . . ? C11 C10 H10B 109.7 . . ? N2 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? N1 C11 C10 110.2(3) . . ? N1 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? N1 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 N4 112.6(4) . . ? C17 C16 H16A 109.1 . . ? N4 C16 H16A 109.1 . . ? C17 C16 H16B 109.1 . . ? N4 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C16 C17 N3 112.5(4) . . ? C16 C17 H17A 109.1 . . ? N3 C17 H17A 109.1 . . ? C16 C17 H17B 109.1 . . ? N3 C17 H17B 109.1 . . ? H17A C17 H17B 107.8 . . ? N4 C18 H18A 109.5 . . ? N4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N4 C19 H19A 109.5 . . ? N4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2A Cl1 O4 116.2(8) . . ? O2A Cl1 O1A 113.1(5) . . ? O4 Cl1 O1A 118.1(9) . . ? O2A Cl1 O1 131.5(7) . . ? O4 Cl1 O1 112.1(5) . . ? O2A Cl1 O3 58.0(5) . . ? O4 Cl1 O3 111.5(5) . . ? O1A Cl1 O3 125.6(8) . . ? O1 Cl1 O3 108.1(5) . . ? O2A Cl1 O3A 110.4(5) . . ? O4 Cl1 O3A 87.4(7) . . ? O1A Cl1 O3A 108.1(6) . . ? O1 Cl1 O3A 75.9(6) . . ? O4 Cl1 O2 110.2(5) . . ? O1A Cl1 O2 76.8(5) . . ? O1 Cl1 O2 108.5(4) . . ? O3 Cl1 O2 106.2(4) . . ? O3A Cl1 O2 157.3(5) . . ? O2A Cl1 O4A 110.4(6) . . ? O1A Cl1 O4A 108.2(5) . . ? O1 Cl1 O4A 113.5(9) . . ? O3 Cl1 O4A 125.6(8) . . ? O3A Cl1 O4A 106.4(4) . . ? O2 Cl1 O4A 92.4(6) . . ? 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 O10 H10 O4 0.829(11) 2.56(3) 3.192(6) 134(3) 1_455 O10 H10 O4A 0.829(11) 2.46(2) 3.145(6) 141(3) 1_455 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.415 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.060 data_compound-2 _database_code_depnum_ccdc_archive 'CCDC 838923' #TrackingRef '17722_web_deposit_cif_file_0_SergioMartinez-Vargas_1360785764.articleADG.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ; catena-(Diaqua-(mu-isophtalato-O,O'')-bis-(N,N,N',N'- tetramethylethylendiamine)-d ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H36 Cu2 N4 O5, Cl O4' _chemical_formula_sum 'C20 H36 Cl Cu2 N4 O9' _chemical_formula_weight 639.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 13.4464(9) _cell_length_b 15.6975(11) _cell_length_c 13.9301(10) _cell_angle_alpha 90.00 _cell_angle_beta 111.165(2) _cell_angle_gamma 90.00 _cell_volume 2742.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 5644 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 32.87 _exptl_crystal_description Prism-lamin _exptl_crystal_colour Blue _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1324 _exptl_absorpt_coefficient_mu 1.701 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7536 _exptl_absorpt_correction_T_max 0.9666 _exptl_absorpt_process_details 'SHELXTL V 6.12 (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 291(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 AXS CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 0.83 _diffrn_reflns_number 30400 _diffrn_reflns_av_R_equivalents 0.1371 _diffrn_reflns_av_sigmaI/netI 0.1136 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.34 _reflns_number_total 5018 _reflns_number_gt 3719 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 6.23A (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0571P)^2^+12.7447P] 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 5018 _refine_ls_number_parameters 415 _refine_ls_number_restraints 296 _refine_ls_R_factor_all 0.1536 _refine_ls_R_factor_gt 0.1102 _refine_ls_wR_factor_ref 0.2111 _refine_ls_wR_factor_gt 0.1944 _refine_ls_goodness_of_fit_ref 1.264 _refine_ls_restrained_S_all 1.245 _refine_ls_shift/su_max 0.007 _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 0.06577(9) 0.31036(6) 0.02735(8) 0.0212(3) Uani 1 1 d . . . Cu2 Cu 0.00470(9) 0.20652(7) 0.20060(9) 0.0246(3) Uani 1 1 d . . . O1 O 0.1080(6) 0.3892(4) 0.1473(5) 0.0346(18) Uani 1 1 d . . . O2 O 0.0792(6) 0.3099(4) 0.2690(5) 0.0366(18) Uani 1 1 d . . . O3 O 0.3632(6) 0.6314(4) 0.3169(6) 0.0379(18) Uani 1 1 d . . . O4 O 0.3137(5) 0.7156(4) 0.4214(5) 0.0311(17) Uani 1 1 d . . . O5 O -0.0452(5) 0.2587(4) 0.0653(5) 0.0277(16) Uani 1 1 d . . . N1 N -0.0035(7) 0.2656(5) -0.1239(7) 0.036(2) Uani 1 1 d . . . N2 N 0.1577(7) 0.3833(5) -0.0299(6) 0.030(2) Uani 1 1 d . . . C1 C 0.0361(10) 0.3213(8) -0.1877(8) 0.046(3) Uani 1 1 d . . . H1A H -0.0074 0.3724 -0.2062 0.055 Uiso 1 1 calc R . . H1B H 0.0308 0.2919 -0.2506 0.055 Uiso 1 1 calc R . . C2 C 0.1497(9) 0.3453(8) -0.1296(8) 0.045(3) Uani 1 1 d . . . H2A H 0.1947 0.2952 -0.1179 0.055 Uiso 1 1 calc R . . H2B H 0.1736 0.3860 -0.1691 0.055 Uiso 1 1 calc R . . C3 C -0.1213(9) 0.2694(9) -0.1639(9) 0.059(4) Uani 1 1 d . . . H3A H -0.1438 0.3252 -0.1520 0.071 Uiso 1 1 calc R . . H3B H -0.1485 0.2278 -0.1293 0.071 Uiso 1 1 calc R . . H3C H -0.1482 0.2578 -0.2365 0.071 Uiso 1 1 calc R . . C4 C 0.0284(11) 0.1765(7) -0.1309(9) 0.057(4) Uani 1 1 d . . . H4A H 0.0011 0.1585 -0.2015 0.068 Uiso 1 1 calc R . . H4B H 0.0000 0.1406 -0.0912 0.068 Uiso 1 1 calc R . . H4C H 0.1048 0.1724 -0.1045 0.068 Uiso 1 1 calc R . . C5 C 0.2708(9) 0.3887(8) 0.0393(9) 0.048(3) Uani 1 1 d . . . H5A H 0.3030 0.3334 0.0458 0.058 Uiso 1 1 calc R . . H5B H 0.2748 0.4084 0.1058 0.058 Uiso 1 1 calc R . . H5C H 0.3079 0.4278 0.0111 0.058 Uiso 1 1 calc R . . C6 C 0.1143(11) 0.4718(7) -0.0465(10) 0.055(4) Uani 1 1 d . . . H6A H 0.1574 0.5066 -0.0728 0.066 Uiso 1 1 calc R . . H6B H 0.1153 0.4948 0.0176 0.066 Uiso 1 1 calc R . . H6C H 0.0423 0.4708 -0.0951 0.066 Uiso 1 1 calc R . . C7 C -0.0079(13) 0.2186(10) 0.4093(10) 0.087(5) Uani 1 1 d . . . H7A H -0.0824 0.2299 0.3738 0.105 Uiso 1 1 calc R A . H7B H 0.0313 0.2710 0.4192 0.105 Uiso 1 1 calc R . . H7C H 0.0024 0.1934 0.4750 0.105 Uiso 1 1 calc R . . C8 C 0.1450(11) 0.1443(8) 0.4024(9) 0.061(4) Uani 1 1 d . . . H8A H 0.1555 0.1148 0.4657 0.073 Uiso 1 1 calc R A . H8B H 0.1819 0.1979 0.4171 0.073 Uiso 1 1 calc R . . H8C H 0.1723 0.1104 0.3601 0.073 Uiso 1 1 calc R . . N3 N 0.0304(8) 0.1595(6) 0.3477(7) 0.044(2) Uani 1 1 d DU A . C9 C -0.0127(19) 0.0703(11) 0.3345(15) 0.055(4) Uani 0.62(2) 1 d PDU A 1 H9A H 0.0444 0.0324 0.3741 0.066 Uiso 0.62(2) 1 calc PR A 1 H9B H -0.0677 0.0675 0.3642 0.066 Uiso 0.62(2) 1 calc PR A 1 C10 C -0.0526(19) 0.0415(11) 0.2403(14) 0.050(4) Uani 0.62(2) 1 d PDU A 1 H10A H -0.1102 0.0026 0.2356 0.059 Uiso 0.62(2) 1 calc PR A 1 H10B H 0.0021 0.0090 0.2266 0.059 Uiso 0.62(2) 1 calc PR A 1 C9A C -0.053(2) 0.0915(19) 0.330(2) 0.050(4) Uani 0.38(2) 1 d PDU A 2 H9C H -0.0160 0.0384 0.3559 0.060 Uiso 0.38(2) 1 calc PR A 2 H9D H -0.0934 0.1051 0.3738 0.060 Uiso 0.38(2) 1 calc PR A 2 C10A C -0.122(3) 0.077(2) 0.237(2) 0.054(5) Uani 0.38(2) 1 d PDU A 2 H10C H -0.1892 0.1014 0.2352 0.065 Uiso 0.38(2) 1 calc PR A 2 H10D H -0.1328 0.0156 0.2322 0.065 Uiso 0.38(2) 1 calc PR A 2 N4 N -0.094(5) 0.107(5) 0.158(4) 0.047(5) Uani 0.52(4) 1 d PDU A 1 C11 C -0.202(2) 0.1261(17) 0.137(3) 0.048(6) Uani 0.52(4) 1 d PDU A 1 H11A H -0.2088 0.1579 0.1938 0.071 Uiso 0.52(4) 1 calc PR A 1 H11B H -0.2421 0.0740 0.1290 0.071 Uiso 0.52(4) 1 calc PR A 1 H11C H -0.2301 0.1592 0.0755 0.071 Uiso 0.52(4) 1 calc PR A 1 C12 C -0.100(3) 0.065(2) 0.056(3) 0.053(6) Uani 0.52(4) 1 d PU A 1 H12A H -0.0296 0.0490 0.0604 0.079 Uiso 0.52(4) 1 calc PR A 1 H12B H -0.1295 0.1047 0.0004 0.079 Uiso 0.52(4) 1 calc PR A 1 H12C H -0.1444 0.0153 0.0437 0.079 Uiso 0.52(4) 1 calc PR A 1 N4A N -0.109(6) 0.103(5) 0.141(5) 0.045(5) Uani 0.48(4) 1 d PDU A 2 C11A C -0.220(2) 0.143(2) 0.082(3) 0.048(6) Uani 0.48(4) 1 d PU A 2 H11D H -0.2213 0.1666 0.0183 0.073 Uiso 0.48(4) 1 calc PR A 2 H11E H -0.2340 0.1875 0.1233 0.073 Uiso 0.48(4) 1 calc PR A 2 H11F H -0.2739 0.0999 0.0690 0.073 Uiso 0.48(4) 1 calc PR A 2 C12A C -0.069(3) 0.049(2) 0.083(3) 0.052(7) Uani 0.48(4) 1 d PDU A 2 H12D H -0.0670 0.0782 0.0238 0.077 Uiso 0.48(4) 1 calc PR A 2 H12E H -0.1149 -0.0002 0.0619 0.077 Uiso 0.48(4) 1 calc PR A 2 H12F H 0.0015 0.0304 0.1249 0.077 Uiso 0.48(4) 1 calc PR A 2 C13 C 0.1251(8) 0.4551(5) 0.3034(7) 0.024(2) Uani 1 1 d . A . C14 C 0.2026(7) 0.5133(5) 0.3040(7) 0.022(2) Uani 1 1 d . . . H14 H 0.2409 0.5049 0.2610 0.026 Uiso 1 1 calc R . . C15 C 0.2243(7) 0.5851(5) 0.3688(7) 0.020(2) Uani 1 1 d . . . C16 C 0.1650(8) 0.5968(6) 0.4309(7) 0.027(2) Uani 1 1 d . . . H16 H 0.1781 0.6438 0.4744 0.032 Uiso 1 1 calc R . . C17 C 0.0856(10) 0.5388(7) 0.4289(8) 0.044(3) Uani 1 1 d . . . H17 H 0.0448 0.5482 0.4694 0.052 Uiso 1 1 calc R . . C18 C 0.0677(10) 0.4682(6) 0.3676(9) 0.043(3) Uani 1 1 d . . . H18 H 0.0168 0.4286 0.3688 0.052 Uiso 1 1 calc R . . C19 C 0.1028(8) 0.3792(6) 0.2340(8) 0.028(2) Uani 1 1 d . . . C20 C 0.3078(7) 0.6492(6) 0.3689(7) 0.022(2) Uani 1 1 d . . . Cl Cl 0.2487(3) 0.6304(2) 0.7846(2) 0.0539(8) Uani 1 1 d DU . . O6 O 0.1628(8) 0.6560(9) 0.8135(9) 0.064(4) Uani 0.674(9) 1 d PDU B 1 O7 O 0.2983(10) 0.5595(7) 0.8454(9) 0.083(4) Uani 0.674(9) 1 d PDU B 1 O8 O 0.3260(10) 0.6958(8) 0.8045(10) 0.095(4) Uani 0.674(9) 1 d PDU B 1 O9 O 0.2104(9) 0.6120(9) 0.6794(6) 0.084(4) Uani 0.674(9) 1 d PDU B 1 O6A O 0.1976(17) 0.6654(15) 0.8475(15) 0.067(6) Uani 0.326(9) 1 d PDU B 2 O8A O 0.3574(9) 0.6185(16) 0.8436(15) 0.077(5) Uani 0.326(9) 1 d PDU B 2 O7A O 0.2047(17) 0.5502(9) 0.7447(19) 0.079(5) Uani 0.326(9) 1 d PDU B 2 O9A O 0.234(2) 0.6856(13) 0.7010(14) 0.089(5) Uani 0.326(9) 1 d PDU 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 0.0294(7) 0.0158(5) 0.0200(6) 0.0015(5) 0.0109(5) 0.0034(5) Cu2 0.0307(7) 0.0143(5) 0.0321(7) -0.0011(5) 0.0154(6) -0.0050(5) O1 0.061(5) 0.024(4) 0.030(4) -0.008(3) 0.030(4) -0.014(3) O2 0.060(5) 0.025(4) 0.028(4) -0.002(3) 0.021(4) -0.019(4) O3 0.038(4) 0.034(4) 0.052(5) -0.012(4) 0.029(4) -0.012(3) O4 0.031(4) 0.024(4) 0.041(4) -0.015(3) 0.017(3) -0.009(3) O5 0.026(4) 0.033(4) 0.024(4) -0.003(3) 0.009(3) -0.011(3) N1 0.035(5) 0.036(5) 0.037(5) 0.003(4) 0.013(5) 0.007(4) N2 0.038(5) 0.026(4) 0.034(5) 0.002(4) 0.022(4) 0.004(4) C1 0.063(8) 0.058(7) 0.029(6) 0.011(6) 0.032(6) 0.007(6) C2 0.039(7) 0.071(8) 0.045(7) -0.004(6) 0.037(6) -0.005(6) C3 0.036(7) 0.085(10) 0.037(7) 0.007(7) -0.009(6) 0.016(7) C4 0.073(10) 0.042(7) 0.047(8) -0.013(6) 0.011(7) 0.011(7) C5 0.045(8) 0.054(7) 0.060(8) 0.010(6) 0.037(7) -0.010(6) C6 0.083(10) 0.034(6) 0.066(9) 0.014(6) 0.047(8) 0.002(6) C7 0.103(13) 0.131(14) 0.053(9) 0.039(9) 0.057(9) 0.032(11) C8 0.079(11) 0.059(8) 0.042(8) 0.012(7) 0.017(8) -0.010(8) N3 0.044(6) 0.043(5) 0.045(5) 0.021(4) 0.015(5) -0.005(4) C9 0.052(8) 0.044(6) 0.057(6) 0.028(6) 0.005(7) -0.008(6) C10 0.054(8) 0.036(7) 0.056(6) 0.025(6) 0.017(7) -0.009(6) C9A 0.052(8) 0.042(7) 0.052(6) 0.025(6) 0.014(7) -0.007(6) C10A 0.052(8) 0.044(8) 0.058(7) 0.028(7) 0.008(7) -0.011(6) N4 0.042(12) 0.045(8) 0.048(13) -0.014(8) 0.011(11) -0.028(8) C11 0.043(11) 0.051(10) 0.051(14) 0.000(10) 0.021(13) -0.030(9) C12 0.049(15) 0.047(11) 0.053(14) -0.021(10) 0.006(13) -0.017(9) N4A 0.040(12) 0.048(8) 0.046(13) -0.011(8) 0.014(11) -0.026(8) C11A 0.036(11) 0.061(12) 0.047(15) -0.012(12) 0.013(14) -0.026(9) C12A 0.045(14) 0.044(11) 0.050(15) -0.027(10) -0.001(13) -0.023(9) C13 0.035(6) 0.021(5) 0.021(5) -0.005(4) 0.016(5) -0.007(4) C14 0.026(6) 0.024(5) 0.019(5) -0.006(4) 0.013(4) -0.007(4) C15 0.021(5) 0.018(4) 0.019(5) -0.003(4) 0.007(4) -0.005(4) C16 0.035(6) 0.021(5) 0.027(6) -0.006(4) 0.015(5) -0.011(4) C17 0.065(8) 0.046(7) 0.044(7) -0.018(6) 0.048(7) -0.018(6) C18 0.067(8) 0.026(5) 0.055(8) -0.007(5) 0.045(7) -0.017(6) C19 0.029(6) 0.023(5) 0.032(6) -0.004(5) 0.011(5) -0.010(4) C20 0.014(5) 0.029(5) 0.019(5) -0.002(4) 0.002(4) -0.003(4) Cl 0.062(2) 0.0625(19) 0.0518(18) 0.0096(16) 0.0383(17) 0.0207(16) O6 0.052(7) 0.082(8) 0.066(8) -0.013(7) 0.029(7) 0.022(5) O7 0.100(8) 0.087(6) 0.076(7) 0.020(6) 0.048(7) 0.056(6) O8 0.083(7) 0.114(8) 0.101(8) 0.000(7) 0.049(7) -0.016(6) O9 0.095(8) 0.105(9) 0.055(4) -0.008(5) 0.030(5) 0.038(7) O6A 0.068(11) 0.085(11) 0.059(11) -0.012(9) 0.035(9) 0.019(11) O8A 0.067(6) 0.099(11) 0.072(10) 0.002(9) 0.033(7) 0.028(8) O7A 0.087(10) 0.075(7) 0.086(10) -0.014(7) 0.045(9) 0.018(8) O9A 0.100(11) 0.107(10) 0.068(9) 0.031(7) 0.040(8) 0.016(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O5 1.933(6) . ? Cu1 O1 1.990(6) . ? Cu1 N2 2.047(8) . ? Cu1 N1 2.094(9) . ? Cu1 O4 2.124(6) 2_545 ? Cu2 O5 1.938(6) . ? Cu2 O2 1.963(6) . ? Cu2 N4 2.00(5) . ? Cu2 N3 2.087(9) . ? Cu2 N4A 2.17(6) . ? Cu2 O3 2.218(7) 2_545 ? O1 C19 1.243(11) . ? O2 C19 1.279(11) . ? O3 C20 1.244(11) . ? O3 Cu2 2.218(7) 2 ? O4 C20 1.259(10) . ? O4 Cu1 2.124(6) 2 ? N1 C1 1.476(13) . ? N1 C4 1.476(13) . ? N1 C3 1.479(14) . ? N2 C2 1.479(13) . ? N2 C5 1.480(14) . ? N2 C6 1.491(13) . ? C1 C2 1.496(16) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N3 1.478(16) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N3 1.471(15) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N3 C9 1.500(16) . ? N3 C9A 1.503(19) . ? C9 C10 1.31(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N4 1.49(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C9A C10A 1.32(2) . ? C9A H9C 0.9700 . ? C9A H9D 0.9700 . ? C10A N4A 1.47(8) . ? C10A H10C 0.9700 . ? C10A H10D 0.9700 . ? N4 C11 1.41(7) . ? N4 C12 1.54(6) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? N4A C12A 1.41(7) . ? N4A C11A 1.56(8) . ? C11A H11D 0.9600 . ? C11A H11E 0.9600 . ? C11A H11F 0.9600 . ? C12A H12D 0.9600 . ? C12A H12E 0.9600 . ? C12A H12F 0.9600 . ? C13 C14 1.384(12) . ? C13 C18 1.392(13) . ? C13 C19 1.495(12) . ? C14 C15 1.406(11) . ? C14 H14 0.9300 . ? C15 C16 1.385(13) . ? C15 C20 1.508(12) . ? C16 C17 1.396(13) . ? C16 H16 0.9300 . ? C17 C18 1.366(14) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? Cl O9 1.397(7) . ? Cl O6A 1.406(8) . ? Cl O8A 1.406(8) . ? Cl O9A 1.408(8) . ? Cl O7 1.411(7) . ? Cl O6 1.412(7) . ? Cl O8 1.415(8) . ? Cl O7A 1.416(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cu1 O1 92.6(3) . . ? O5 Cu1 N2 167.5(3) . . ? O1 Cu1 N2 87.1(3) . . ? O5 Cu1 N1 91.6(3) . . ? O1 Cu1 N1 160.4(3) . . ? N2 Cu1 N1 84.7(3) . . ? O5 Cu1 O4 100.6(3) . 2_545 ? O1 Cu1 O4 101.6(3) . 2_545 ? N2 Cu1 O4 91.6(3) . 2_545 ? N1 Cu1 O4 96.4(3) . 2_545 ? O5 Cu2 O2 93.4(3) . . ? O5 Cu2 N4 95(2) . . ? O2 Cu2 N4 163.4(19) . . ? O5 Cu2 N3 168.7(3) . . ? O2 Cu2 N3 86.6(3) . . ? N4 Cu2 N3 83(2) . . ? O5 Cu2 N4A 90(2) . . ? O2 Cu2 N4A 165(2) . . ? N4 Cu2 N4A 5(4) . . ? N3 Cu2 N4A 87(2) . . ? O5 Cu2 O3 97.3(3) . 2_545 ? O2 Cu2 O3 101.8(3) . 2_545 ? N4 Cu2 O3 92(2) . 2_545 ? N3 Cu2 O3 93.7(3) . 2_545 ? N4A Cu2 O3 92(2) . 2_545 ? C19 O1 Cu1 129.6(6) . . ? C19 O2 Cu2 132.2(6) . . ? C20 O3 Cu2 128.1(6) . 2 ? C20 O4 Cu1 131.0(6) . 2 ? Cu1 O5 Cu2 114.4(3) . . ? C1 N1 C4 110.3(9) . . ? C1 N1 C3 108.6(9) . . ? C4 N1 C3 108.1(10) . . ? C1 N1 Cu1 106.3(7) . . ? C4 N1 Cu1 110.5(7) . . ? C3 N1 Cu1 113.1(7) . . ? C2 N2 C5 110.1(8) . . ? C2 N2 C6 109.8(9) . . ? C5 N2 C6 107.5(9) . . ? C2 N2 Cu1 106.9(6) . . ? C5 N2 Cu1 113.6(6) . . ? C6 N2 Cu1 108.9(6) . . ? N1 C1 C2 110.1(9) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.2 . . ? N2 C2 C1 108.9(8) . . ? N2 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? N2 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C8 N3 C7 108.7(11) . . ? C8 N3 C9 101.5(12) . . ? C7 N3 C9 117.2(13) . . ? C8 N3 C9A 123.3(16) . . ? C7 N3 C9A 98.2(18) . . ? C9 N3 C9A 23.9(16) . . ? C8 N3 Cu2 109.7(7) . . ? C7 N3 Cu2 112.3(7) . . ? C9 N3 Cu2 106.9(9) . . ? C9A N3 Cu2 104.2(12) . . ? C10 C9 N3 116.5(15) . . ? C10 C9 H9A 108.2 . . ? N3 C9 H9A 108.2 . . ? C10 C9 H9B 108.2 . . ? N3 C9 H9B 108.2 . . ? H9A C9 H9B 107.3 . . ? C9 C10 N4 116(2) . . ? C9 C10 H10A 108.3 . . ? N4 C10 H10A 108.3 . . ? C9 C10 H10B 108.3 . . ? N4 C10 H10B 108.3 . . ? H10A C10 H10B 107.4 . . ? C10A C9A N3 120(2) . . ? C10A C9A H9C 107.3 . . ? N3 C9A H9C 107.3 . . ? C10A C9A H9D 107.3 . . ? N3 C9A H9D 107.3 . . ? H9C C9A H9D 106.9 . . ? C9A C10A N4A 125(3) . . ? C9A C10A H10C 106.1 . . ? N4A C10A H10C 106.1 . . ? C9A C10A H10D 106.1 . . ? N4A C10A H10D 106.1 . . ? H10C C10A H10D 106.3 . . ? C11 N4 C10 112(5) . . ? C11 N4 C12 101(4) . . ? C10 N4 C12 107(5) . . ? C11 N4 Cu2 115(4) . . ? C10 N4 Cu2 107(3) . . ? C12 N4 Cu2 114(5) . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C12A N4A C10A 123(7) . . ? C12A N4A C11A 116(4) . . ? C10A N4A C11A 100(5) . . ? C12A N4A Cu2 108(5) . . ? C10A N4A Cu2 100(2) . . ? C11A N4A Cu2 108(4) . . ? N4A C11A H11D 109.5 . . ? N4A C11A H11E 109.5 . . ? H11D C11A H11E 109.5 . . ? N4A C11A H11F 109.5 . . ? H11D C11A H11F 109.5 . . ? H11E C11A H11F 109.5 . . ? N4A C12A H12D 109.5 . . ? N4A C12A H12E 109.5 . . ? H12D C12A H12E 109.5 . . ? N4A C12A H12F 109.5 . . ? H12D C12A H12F 109.5 . . ? H12E C12A H12F 109.5 . . ? C14 C13 C18 119.3(8) . . ? C14 C13 C19 120.4(8) . . ? C18 C13 C19 120.4(9) . . ? C13 C14 C15 121.0(8) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C16 C15 C14 118.4(8) . . ? C16 C15 C20 120.5(8) . . ? C14 C15 C20 121.1(8) . . ? C15 C16 C17 120.6(9) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C18 C17 C16 120.1(9) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C13 120.6(10) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? O1 C19 O2 125.9(9) . . ? O1 C19 C13 117.3(8) . . ? O2 C19 C13 116.7(8) . . ? O3 C20 O4 126.7(9) . . ? O3 C20 C15 116.9(8) . . ? O4 C20 C15 116.4(8) . . ? O9 Cl O6A 131.0(11) . . ? O9 Cl O8A 119.8(11) . . ? O6A Cl O8A 109.0(7) . . ? O9 Cl O9A 51.0(10) . . ? O6A Cl O9A 108.8(7) . . ? O8A Cl O9A 111.6(9) . . ? O9 Cl O7 112.4(7) . . ? O6A Cl O7 99.6(11) . . ? O8A Cl O7 51.6(11) . . ? O9A Cl O7 151.1(11) . . ? O9 Cl O6 109.1(6) . . ? O6A Cl O6 22.6(11) . . ? O8A Cl O6 131.0(10) . . ? O9A Cl O6 100.2(12) . . ? O7 Cl O6 108.2(6) . . ? O9 Cl O8 108.8(6) . . ? O6A Cl O8 94.8(11) . . ? O8A Cl O8 56.4(10) . . ? O9A Cl O8 65.6(10) . . ? O7 Cl O8 107.5(6) . . ? O6 Cl O8 110.8(8) . . ? O9 Cl O7A 57.4(10) . . ? O6A Cl O7A 111.3(9) . . ? O8A Cl O7A 108.1(6) . . ? O9A Cl O7A 108.0(7) . . ? O7 Cl O7A 64.8(10) . . ? O6 Cl O7A 95.5(11) . . ? O8 Cl O7A 153.5(11) . . ? 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 O5 Cu1 O1 C19 30.0(9) . . . . ? N2 Cu1 O1 C19 -162.5(9) . . . . ? N1 Cu1 O1 C19 132.2(11) . . . . ? O4 Cu1 O1 C19 -71.5(9) 2_545 . . . ? O5 Cu2 O2 C19 -12.0(9) . . . . ? N4 Cu2 O2 C19 -131(8) . . . . ? N3 Cu2 O2 C19 179.4(10) . . . . ? N4A Cu2 O2 C19 -114(8) . . . . ? O3 Cu2 O2 C19 86.3(9) 2_545 . . . ? O1 Cu1 O5 Cu2 -59.2(4) . . . . ? N2 Cu1 O5 Cu2 -147.7(12) . . . . ? N1 Cu1 O5 Cu2 140.0(4) . . . . ? O4 Cu1 O5 Cu2 43.1(4) 2_545 . . . ? O2 Cu2 O5 Cu1 53.0(4) . . . . ? N4 Cu2 O5 Cu1 -142(2) . . . . ? N3 Cu2 O5 Cu1 143.0(15) . . . . ? N4A Cu2 O5 Cu1 -142(2) . . . . ? O3 Cu2 O5 Cu1 -49.4(4) 2_545 . . . ? O5 Cu1 N1 C1 157.7(7) . . . . ? O1 Cu1 N1 C1 55.3(13) . . . . ? N2 Cu1 N1 C1 -10.4(7) . . . . ? O4 Cu1 N1 C1 -101.4(7) 2_545 . . . ? O5 Cu1 N1 C4 -82.7(8) . . . . ? O1 Cu1 N1 C4 174.9(9) . . . . ? N2 Cu1 N1 C4 109.2(8) . . . . ? O4 Cu1 N1 C4 18.2(8) 2_545 . . . ? O5 Cu1 N1 C3 38.6(8) . . . . ? O1 Cu1 N1 C3 -63.8(13) . . . . ? N2 Cu1 N1 C3 -129.5(8) . . . . ? O4 Cu1 N1 C3 139.5(8) 2_545 . . . ? O5 Cu1 N2 C2 -90.6(15) . . . . ? O1 Cu1 N2 C2 -179.8(7) . . . . ? N1 Cu1 N2 C2 -17.6(7) . . . . ? O4 Cu1 N2 C2 78.7(7) 2_545 . . . ? O5 Cu1 N2 C5 147.8(13) . . . . ? O1 Cu1 N2 C5 58.6(7) . . . . ? N1 Cu1 N2 C5 -139.2(7) . . . . ? O4 Cu1 N2 C5 -42.9(7) 2_545 . . . ? O5 Cu1 N2 C6 28.0(18) . . . . ? O1 Cu1 N2 C6 -61.2(7) . . . . ? N1 Cu1 N2 C6 101.0(7) . . . . ? O4 Cu1 N2 C6 -162.7(7) 2_545 . . . ? C4 N1 C1 C2 -82.9(11) . . . . ? C3 N1 C1 C2 158.8(10) . . . . ? Cu1 N1 C1 C2 36.9(10) . . . . ? C5 N2 C2 C1 166.5(9) . . . . ? C6 N2 C2 C1 -75.4(11) . . . . ? Cu1 N2 C2 C1 42.6(10) . . . . ? N1 C1 C2 N2 -54.5(12) . . . . ? O5 Cu2 N3 C8 -158.6(14) . . . . ? O2 Cu2 N3 C8 -67.9(8) . . . . ? N4 Cu2 N3 C8 125(2) . . . . ? N4A Cu2 N3 C8 126(2) . . . . ? O3 Cu2 N3 C8 33.7(8) 2_545 . . . ? O5 Cu2 N3 C7 -38(2) . . . . ? O2 Cu2 N3 C7 53.0(9) . . . . ? N4 Cu2 N3 C7 -114(2) . . . . ? N4A Cu2 N3 C7 -113(2) . . . . ? O3 Cu2 N3 C7 154.6(9) 2_545 . . . ? O5 Cu2 N3 C9 92(2) . . . . ? O2 Cu2 N3 C9 -177.1(12) . . . . ? N4 Cu2 N3 C9 16(2) . . . . ? N4A Cu2 N3 C9 17(2) . . . . ? O3 Cu2 N3 C9 -75.5(12) 2_545 . . . ? O5 Cu2 N3 C9A 68(2) . . . . ? O2 Cu2 N3 C9A 158.2(17) . . . . ? N4 Cu2 N3 C9A -9(3) . . . . ? N4A Cu2 N3 C9A -8(3) . . . . ? O3 Cu2 N3 C9A -100.1(17) 2_545 . . . ? C8 N3 C9 C10 -113(2) . . . . ? C7 N3 C9 C10 128(2) . . . . ? C9A N3 C9 C10 88(4) . . . . ? Cu2 N3 C9 C10 1(2) . . . . ? N3 C9 C10 N4 -26(4) . . . . ? C8 N3 C9A C10A -128(3) . . . . ? C7 N3 C9A C10A 113(3) . . . . ? C9 N3 C9A C10A -102(5) . . . . ? Cu2 N3 C9A C10A -2(4) . . . . ? N3 C9A C10A N4A 19(7) . . . . ? C9 C10 N4 C11 -89(3) . . . . ? C9 C10 N4 C12 161(3) . . . . ? C9 C10 N4 Cu2 38(5) . . . . ? O5 Cu2 N4 C11 -71(4) . . . . ? O2 Cu2 N4 C11 48(10) . . . . ? N3 Cu2 N4 C11 98(4) . . . . ? N4A Cu2 N4 C11 -69(47) . . . . ? O3 Cu2 N4 C11 -169(4) 2_545 . . . ? O5 Cu2 N4 C10 164(3) . . . . ? O2 Cu2 N4 C10 -77(9) . . . . ? N3 Cu2 N4 C10 -27(3) . . . . ? N4A Cu2 N4 C10 166(50) . . . . ? O3 Cu2 N4 C10 66(3) 2_545 . . . ? O5 Cu2 N4 C12 46(5) . . . . ? O2 Cu2 N4 C12 165(3) . . . . ? N3 Cu2 N4 C12 -145(5) . . . . ? N4A Cu2 N4 C12 48(44) . . . . ? O3 Cu2 N4 C12 -52(5) 2_545 . . . ? C9A C10A N4A C12A 97(6) . . . . ? C9A C10A N4A C11A -133(4) . . . . ? C9A C10A N4A Cu2 -22(6) . . . . ? O5 Cu2 N4A C12A 76(5) . . . . ? O2 Cu2 N4A C12A 178(4) . . . . ? N4 Cu2 N4A C12A -101(49) . . . . ? N3 Cu2 N4A C12A -115(5) . . . . ? O3 Cu2 N4A C12A -21(5) 2_545 . . . ? O5 Cu2 N4A C10A -154(4) . . . . ? O2 Cu2 N4A C10A -52(11) . . . . ? N4 Cu2 N4A C10A 28(44) . . . . ? N3 Cu2 N4A C10A 15(4) . . . . ? O3 Cu2 N4A C10A 108(4) 2_545 . . . ? O5 Cu2 N4A C11A -50(4) . . . . ? O2 Cu2 N4A C11A 52(10) . . . . ? N4 Cu2 N4A C11A 133(49) . . . . ? N3 Cu2 N4A C11A 119(4) . . . . ? O3 Cu2 N4A C11A -147(4) 2_545 . . . ? C18 C13 C14 C15 0.3(14) . . . . ? C19 C13 C14 C15 179.9(9) . . . . ? C13 C14 C15 C16 -1.0(13) . . . . ? C13 C14 C15 C20 -179.4(8) . . . . ? C14 C15 C16 C17 -0.1(14) . . . . ? C20 C15 C16 C17 178.3(9) . . . . ? C15 C16 C17 C18 1.9(17) . . . . ? C16 C17 C18 C13 -2.7(18) . . . . ? C14 C13 C18 C17 1.6(17) . . . . ? C19 C13 C18 C17 -178.0(10) . . . . ? Cu1 O1 C19 O2 8.4(16) . . . . ? Cu1 O1 C19 C13 -170.9(6) . . . . ? Cu2 O2 C19 O1 -20.1(16) . . . . ? Cu2 O2 C19 C13 159.1(7) . . . . ? C14 C13 C19 O1 -36.7(14) . . . . ? C18 C13 C19 O1 142.9(11) . . . . ? C14 C13 C19 O2 143.9(9) . . . . ? C18 C13 C19 O2 -36.5(14) . . . . ? Cu2 O3 C20 O4 1.9(15) 2 . . . ? Cu2 O3 C20 C15 -178.6(6) 2 . . . ? Cu1 O4 C20 O3 -15.3(15) 2 . . . ? Cu1 O4 C20 C15 165.2(6) 2 . . . ? C16 C15 C20 O3 175.0(9) . . . . ? C14 C15 C20 O3 -6.7(13) . . . . ? C16 C15 C20 O4 -5.5(13) . . . . ? C14 C15 C20 O4 172.8(8) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.618 _refine_diff_density_min -1.200 _refine_diff_density_rms 0.132 data_compound-3 _database_code_depnum_ccdc_archive 'CCDC 838924' #TrackingRef '17722_web_deposit_cif_file_0_SergioMartinez-Vargas_1360785764.articleADG.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ; catena-(Diaqua-(mu-5-nitroisophtalato-O,O'')-bis-(N,N,N',N'- tetramethylethylendia ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H36 Cu2 N5 O7, Cl O4' _chemical_formula_sum 'C20 H36 Cl Cu2 N5 O11' _chemical_formula_weight 685.07 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 13.4288(7) _cell_length_b 15.5866(8) _cell_length_c 14.6967(8) _cell_angle_alpha 90.00 _cell_angle_beta 111.8970(10) _cell_angle_gamma 90.00 _cell_volume 2854.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 6662 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 30.70 _exptl_crystal_description prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method . _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 1.646 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7707 _exptl_absorpt_correction_T_max 0.9039 _exptl_absorpt_process_details 'SHELXTL V 6.12 (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 291(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 AXS CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 0.83 _diffrn_reflns_number 23698 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.0715 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.34 _reflns_number_total 5216 _reflns_number_gt 3375 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 6.23A (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0340P)^2^] 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 5216 _refine_ls_number_parameters 400 _refine_ls_number_restraints 161 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 0.854 _refine_ls_restrained_S_all 0.943 _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 0.42443(4) 0.30998(3) 0.97313(3) 0.03486(15) Uani 1 1 d . . . Cu2 Cu 0.50382(4) 0.20406(3) 0.82022(3) 0.03429(14) Uani 1 1 d . . . O1 O 0.3077(2) 0.21089(17) 0.9190(2) 0.0464(7) Uani 1 1 d . . . O2 O 0.3666(2) 0.12852(17) 0.8257(2) 0.0469(7) Uani 1 1 d . . . O3 O 0.0688(2) -0.19044(16) 0.75031(18) 0.0444(7) Uani 1 1 d . . . O4 O 0.1152(2) -0.11367(16) 0.6433(2) 0.0474(8) Uani 1 1 d . . . O5 O -0.1026(3) 0.0254(3) 0.9028(3) 0.0996(13) Uani 1 1 d . . . O6 O -0.0111(3) 0.1349(2) 0.9732(3) 0.0892(12) Uani 1 1 d . . . O7 O 0.5411(2) 0.25931(16) 0.94631(18) 0.0379(7) Uani 1 1 d D . . H7A H 0.594(2) 0.3015(17) 0.947(3) 0.046 Uiso 1 1 d D . . N1 N 0.4889(3) 0.2681(2) 1.1188(2) 0.0493(9) Uani 1 1 d . . . N2 N 0.3250(3) 0.3836(2) 1.0184(3) 0.0459(9) Uani 1 1 d . . . N3 N 0.6177(3) 0.1092(2) 0.8798(3) 0.0482(9) Uani 1 1 d . . . N4 N 0.4858(3) 0.1535(2) 0.6869(2) 0.0445(9) Uani 1 1 d . . . N5 N -0.0236(3) 0.0703(2) 0.9221(3) 0.0474(9) Uani 1 1 d . . . C1 C 0.2152(3) 0.0832(2) 0.8558(3) 0.0286(9) Uani 1 1 d . . . C2 C 0.1995(3) 0.0104(2) 0.7984(3) 0.0324(9) Uani 1 1 d . . . H2 H 0.2469 -0.0011 0.7673 0.039 Uiso 1 1 calc R . . C3 C 0.1158(3) -0.0456(2) 0.7856(3) 0.0317(9) Uani 1 1 d . . . C4 C 0.0425(3) -0.0274(2) 0.8290(3) 0.0330(9) Uani 1 1 d . . . H4 H -0.0147 -0.0640 0.8213 0.040 Uiso 1 1 calc R . . C5 C 0.0567(3) 0.0465(2) 0.8836(3) 0.0336(9) Uani 1 1 d . . . C6 C 0.1419(3) 0.1010(2) 0.8993(3) 0.0345(9) Uani 1 1 d . . . H6 H 0.1503 0.1493 0.9386 0.041 Uiso 1 1 calc R . . C7 C 0.3052(3) 0.1458(2) 0.8683(3) 0.0313(9) Uani 1 1 d . . . C8 C 0.0982(3) -0.1239(2) 0.7207(3) 0.0353(9) Uani 1 1 d . . . C9 C 0.4424(4) 0.3230(3) 1.1748(3) 0.0649(14) Uani 1 1 d . . . H9A H 0.4844 0.3751 1.1951 0.078 Uiso 1 1 calc R . . H9B H 0.4441 0.2930 1.2332 0.078 Uiso 1 1 calc R . . C10 C 0.3281(4) 0.3453(3) 1.1117(3) 0.0635(14) Uani 1 1 d . . . H10A H 0.2841 0.2940 1.0982 0.076 Uiso 1 1 calc R . . H10B H 0.2996 0.3857 1.1460 0.076 Uiso 1 1 calc R . . C11 C 0.4606(5) 0.1774(3) 1.1253(3) 0.0780(17) Uani 1 1 d . . . H11A H 0.4908 0.1589 1.1924 0.117 Uiso 1 1 calc R . . H11B H 0.4888 0.1427 1.0864 0.117 Uiso 1 1 calc R . . H11C H 0.3840 0.1715 1.1012 0.117 Uiso 1 1 calc R . . C12 C 0.6075(4) 0.2753(3) 1.1614(3) 0.0771(17) Uani 1 1 d . . . H12A H 0.6281 0.3334 1.1559 0.116 Uiso 1 1 calc R . . H12B H 0.6379 0.2379 1.1267 0.116 Uiso 1 1 calc R . . H12C H 0.6333 0.2591 1.2293 0.116 Uiso 1 1 calc R . . C13 C 0.3667(4) 0.4729(3) 1.0341(4) 0.0689(15) Uani 1 1 d . . . H13A H 0.3233 0.5072 1.0592 0.103 Uiso 1 1 calc R . . H13B H 0.3643 0.4964 0.9729 0.103 Uiso 1 1 calc R . . H13C H 0.4395 0.4727 1.0803 0.103 Uiso 1 1 calc R . . C14 C 0.2126(4) 0.3853(3) 0.9485(3) 0.0663(14) Uani 1 1 d . . . H14A H 0.1708 0.4210 0.9741 0.099 Uiso 1 1 calc R . . H14B H 0.1839 0.3281 0.9391 0.099 Uiso 1 1 calc R . . H14C H 0.2098 0.4080 0.8869 0.099 Uiso 1 1 calc R . . C15 C 0.6351(5) 0.0687(4) 0.7987(4) 0.0895(19) Uani 1 1 d . . . H15A H 0.6603 0.0105 0.8166 0.107 Uiso 1 1 calc R . . H15B H 0.6901 0.0998 0.7844 0.107 Uiso 1 1 calc R . . C16 C 0.5340(4) 0.0669(3) 0.7090(4) 0.0826(18) Uani 1 1 d . . . H16A H 0.5499 0.0463 0.6536 0.099 Uiso 1 1 calc R . . H16B H 0.4831 0.0277 0.7193 0.099 Uiso 1 1 calc R . . C17 C 0.5792(4) 0.0465(3) 0.9344(4) 0.0754(16) Uani 1 1 d . . . H17A H 0.5139 0.0207 0.8909 0.113 Uiso 1 1 calc R . . H17B H 0.5660 0.0752 0.9867 0.113 Uiso 1 1 calc R . . H17C H 0.6326 0.0029 0.9612 0.113 Uiso 1 1 calc R . . C18 C 0.7212(4) 0.1421(3) 0.9527(4) 0.0700(15) Uani 1 1 d . . . H18A H 0.7719 0.0959 0.9739 0.105 Uiso 1 1 calc R . . H18B H 0.7092 0.1656 1.0081 0.105 Uiso 1 1 calc R . . H18C H 0.7490 0.1859 0.9228 0.105 Uiso 1 1 calc R . . C19 C 0.5402(5) 0.2075(4) 0.6375(4) 0.0901(19) Uani 1 1 d . . . H19A H 0.5392 0.1792 0.5792 0.135 Uiso 1 1 calc R . . H19B H 0.6132 0.2170 0.6808 0.135 Uiso 1 1 calc R . . H19C H 0.5037 0.2616 0.6204 0.135 Uiso 1 1 calc R . . C20 C 0.3730(4) 0.1449(3) 0.6206(3) 0.0666(14) Uani 1 1 d . . . H20A H 0.3408 0.2008 0.6057 0.100 Uiso 1 1 calc R . . H20B H 0.3350 0.1111 0.6518 0.100 Uiso 1 1 calc R . . H20C H 0.3694 0.1173 0.5611 0.100 Uiso 1 1 calc R . . Cl1 Cl 0.27654(12) 0.13839(9) 0.31789(11) 0.0764(4) Uani 1 1 d DU . . O8 O 0.3412(7) 0.0751(5) 0.3742(5) 0.121(2) Uani 0.596(6) 1 d PDU A 1 O9 O 0.1848(5) 0.1532(5) 0.3426(7) 0.095(2) Uani 0.596(6) 1 d PDU A 1 O10 O 0.3322(6) 0.2177(4) 0.3284(6) 0.119(2) Uani 0.596(6) 1 d PDU A 1 O11 O 0.2391(8) 0.1178(5) 0.2162(4) 0.120(3) Uani 0.596(6) 1 d PDU A 1 O8A O 0.2670(10) 0.0462(4) 0.3234(8) 0.091(2) Uani 0.404(6) 1 d PDU A 2 O9A O 0.2123(9) 0.1759(7) 0.3627(10) 0.105(3) Uani 0.404(6) 1 d PDU A 2 O10A O 0.3857(6) 0.1573(9) 0.3716(7) 0.126(3) Uani 0.404(6) 1 d PDU A 2 O11A O 0.2497(10) 0.1608(7) 0.2205(5) 0.108(3) Uani 0.404(6) 1 d PDU A 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 0.0429(3) 0.0296(3) 0.0337(3) -0.0023(2) 0.0162(2) -0.0041(2) Cu2 0.0362(3) 0.0271(3) 0.0428(3) 0.0024(2) 0.0186(2) 0.0047(2) O1 0.0466(18) 0.0427(17) 0.0528(18) -0.0184(15) 0.0221(15) -0.0178(14) O2 0.0466(18) 0.0433(17) 0.062(2) -0.0140(15) 0.0326(17) -0.0147(14) O3 0.066(2) 0.0286(15) 0.0429(17) -0.0035(13) 0.0249(15) -0.0143(15) O4 0.067(2) 0.0394(16) 0.0483(19) -0.0131(14) 0.0355(17) -0.0205(15) O5 0.072(3) 0.109(3) 0.136(4) -0.038(3) 0.060(3) -0.010(3) O6 0.088(3) 0.080(3) 0.128(3) -0.043(2) 0.073(3) -0.014(2) O7 0.0355(16) 0.0366(16) 0.0398(16) -0.0004(13) 0.0117(13) -0.0035(13) N1 0.063(3) 0.047(2) 0.034(2) -0.0070(17) 0.0136(19) -0.006(2) N2 0.061(3) 0.041(2) 0.047(2) -0.0057(17) 0.031(2) -0.0066(19) N3 0.045(2) 0.041(2) 0.062(3) 0.0051(19) 0.024(2) 0.0126(18) N4 0.047(2) 0.039(2) 0.052(2) -0.0073(17) 0.024(2) 0.0042(18) N5 0.041(2) 0.044(2) 0.066(3) -0.013(2) 0.029(2) -0.0082(19) C1 0.030(2) 0.026(2) 0.028(2) 0.0018(17) 0.0087(18) -0.0017(17) C2 0.035(2) 0.031(2) 0.034(2) 0.0012(18) 0.017(2) 0.0004(19) C3 0.038(2) 0.026(2) 0.029(2) 0.0021(17) 0.0112(19) -0.0029(18) C4 0.031(2) 0.034(2) 0.038(2) 0.0032(18) 0.016(2) -0.0067(18) C5 0.036(2) 0.035(2) 0.035(2) -0.0020(19) 0.020(2) 0.0017(19) C6 0.041(2) 0.032(2) 0.030(2) -0.0048(18) 0.014(2) -0.0025(19) C7 0.027(2) 0.034(2) 0.028(2) 0.0027(18) 0.0049(19) -0.0013(18) C8 0.035(2) 0.034(2) 0.039(3) -0.0047(19) 0.016(2) -0.0039(19) C9 0.093(4) 0.071(3) 0.037(3) -0.008(2) 0.031(3) -0.008(3) C10 0.083(4) 0.069(3) 0.059(3) -0.005(3) 0.049(3) -0.004(3) C11 0.122(5) 0.051(3) 0.050(3) 0.013(2) 0.019(3) -0.013(3) C12 0.067(4) 0.103(4) 0.042(3) -0.008(3) -0.003(3) 0.003(3) C13 0.101(4) 0.042(3) 0.083(4) -0.015(3) 0.057(3) -0.004(3) C14 0.061(3) 0.073(4) 0.073(4) 0.001(3) 0.035(3) 0.012(3) C15 0.100(5) 0.086(4) 0.085(4) 0.002(3) 0.038(4) 0.058(4) C16 0.080(4) 0.064(4) 0.091(4) -0.034(3) 0.017(3) 0.022(3) C17 0.080(4) 0.049(3) 0.090(4) 0.030(3) 0.023(3) 0.012(3) C18 0.043(3) 0.075(4) 0.083(4) 0.004(3) 0.013(3) 0.012(3) C19 0.121(5) 0.099(4) 0.086(4) -0.029(3) 0.079(4) -0.028(4) C20 0.070(4) 0.081(4) 0.043(3) -0.012(3) 0.015(3) 0.005(3) Cl1 0.0826(10) 0.0719(9) 0.0808(10) -0.0105(8) 0.0375(9) 0.0119(8) O8 0.126(5) 0.119(4) 0.110(4) 0.003(4) 0.035(4) 0.054(4) O9 0.097(4) 0.065(4) 0.148(5) -0.014(4) 0.074(4) -0.004(3) O10 0.102(5) 0.112(4) 0.160(5) -0.027(4) 0.069(4) -0.031(3) O11 0.149(5) 0.110(5) 0.088(2) -0.028(3) 0.029(3) 0.043(5) O8A 0.117(6) 0.072(2) 0.117(6) 0.000(4) 0.080(5) 0.012(4) O9A 0.128(5) 0.080(5) 0.133(6) -0.031(5) 0.079(5) 0.004(5) O10A 0.091(3) 0.133(6) 0.142(5) -0.001(6) 0.029(4) -0.012(4) O11A 0.135(6) 0.105(6) 0.096(3) 0.021(4) 0.055(3) 0.021(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 O7 1.922(3) . ? Cu1 O4 1.986(3) 2_556 ? Cu1 N2 2.050(3) . ? Cu1 N1 2.092(3) . ? Cu1 O1 2.132(3) . ? Cu2 O7 1.932(3) . ? Cu2 O3 1.994(2) 2_556 ? Cu2 N4 2.041(3) . ? Cu2 N3 2.072(3) . ? Cu2 O2 2.213(3) . ? O1 C7 1.252(4) . ? O2 C7 1.236(4) . ? O3 C8 1.245(4) . ? O3 Cu2 1.994(2) 2_546 ? O4 C8 1.252(4) . ? O4 Cu1 1.986(3) 2_546 ? O5 N5 1.214(4) . ? O6 N5 1.229(4) . ? O7 H7A 0.970(11) . ? N1 C11 1.476(5) . ? N1 C9 1.476(5) . ? N1 C12 1.483(6) . ? N2 C14 1.476(5) . ? N2 C10 1.481(5) . ? N2 C13 1.486(5) . ? N3 C15 1.443(6) . ? N3 C17 1.474(5) . ? N3 C18 1.494(5) . ? N4 C19 1.470(6) . ? N4 C20 1.471(5) . ? N4 C16 1.479(5) . ? N5 C5 1.441(5) . ? C1 C2 1.382(5) . ? C1 C6 1.387(5) . ? C1 C7 1.510(5) . ? C2 C3 1.379(5) . ? C2 H2 0.9300 . ? C3 C4 1.387(5) . ? C3 C8 1.512(5) . ? C4 C5 1.375(5) . ? C4 H4 0.9300 . ? C5 C6 1.374(5) . ? C6 H6 0.9300 . ? C9 C10 1.508(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.499(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? Cl1 O8 1.370(5) . ? Cl1 O11A 1.384(6) . ? Cl1 O9A 1.393(6) . ? Cl1 O10A 1.413(6) . ? Cl1 O10 1.423(5) . ? Cl1 O11 1.424(5) . ? Cl1 O9 1.427(5) . ? Cl1 O8A 1.447(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 O7 Cu1 O4 92.67(11) . 2_556 ? O7 Cu1 N2 167.37(13) . . ? O4 Cu1 N2 86.94(12) 2_556 . ? O7 Cu1 N1 91.38(13) . . ? O4 Cu1 N1 160.70(13) 2_556 . ? N2 Cu1 N1 85.02(14) . . ? O7 Cu1 O1 99.66(11) . . ? O4 Cu1 O1 100.89(12) 2_556 . ? N2 Cu1 O1 92.80(12) . . ? N1 Cu1 O1 97.01(12) . . ? O7 Cu2 O3 91.86(10) . 2_556 ? O7 Cu2 N4 171.22(13) . . ? O3 Cu2 N4 87.67(12) 2_556 . ? O7 Cu2 N3 91.51(13) . . ? O3 Cu2 N3 161.67(13) 2_556 . ? N4 Cu2 N3 86.27(14) . . ? O7 Cu2 O2 97.08(11) . . ? O3 Cu2 O2 101.83(11) 2_556 . ? N4 Cu2 O2 91.59(12) . . ? N3 Cu2 O2 95.62(12) . . ? C7 O1 Cu1 131.4(3) . . ? C7 O2 Cu2 128.6(2) . . ? C8 O3 Cu2 131.5(3) . 2_546 ? C8 O4 Cu1 128.7(2) . 2_546 ? Cu1 O7 Cu2 116.14(13) . . ? Cu1 O7 H7A 112(2) . . ? Cu2 O7 H7A 104(2) . . ? C11 N1 C9 110.3(4) . . ? C11 N1 C12 107.8(4) . . ? C9 N1 C12 109.4(4) . . ? C11 N1 Cu1 110.3(3) . . ? C9 N1 Cu1 106.8(3) . . ? C12 N1 Cu1 112.2(3) . . ? C14 N2 C10 108.7(4) . . ? C14 N2 C13 108.6(4) . . ? C10 N2 C13 110.8(3) . . ? C14 N2 Cu1 113.9(3) . . ? C10 N2 Cu1 106.2(3) . . ? C13 N2 Cu1 108.7(3) . . ? C15 N3 C17 111.0(4) . . ? C15 N3 C18 110.3(4) . . ? C17 N3 C18 105.0(4) . . ? C15 N3 Cu2 106.5(3) . . ? C17 N3 Cu2 110.5(3) . . ? C18 N3 Cu2 113.6(3) . . ? C19 N4 C20 107.7(4) . . ? C19 N4 C16 111.9(4) . . ? C20 N4 C16 108.7(4) . . ? C19 N4 Cu2 110.5(3) . . ? C20 N4 Cu2 113.3(3) . . ? C16 N4 Cu2 104.8(3) . . ? O5 N5 O6 121.6(4) . . ? O5 N5 C5 118.4(4) . . ? O6 N5 C5 120.0(4) . . ? C2 C1 C6 118.2(3) . . ? C2 C1 C7 122.5(3) . . ? C6 C1 C7 119.2(3) . . ? C3 C2 C1 122.3(4) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C2 C3 C4 119.3(3) . . ? C2 C3 C8 121.7(3) . . ? C4 C3 C8 119.0(3) . . ? C5 C4 C3 118.2(3) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C6 C5 C4 122.7(4) . . ? C6 C5 N5 118.2(3) . . ? C4 C5 N5 119.0(4) . . ? C5 C6 C1 119.3(3) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? O2 C7 O1 127.1(4) . . ? O2 C7 C1 116.9(3) . . ? O1 C7 C1 116.0(3) . . ? O3 C8 O4 127.8(4) . . ? O3 C8 C3 116.6(3) . . ? O4 C8 C3 115.6(3) . . ? N1 C9 C10 109.6(4) . . ? N1 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? N1 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? N2 C10 C9 109.4(4) . . ? N2 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? N2 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 C16 111.2(4) . . ? N3 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? N3 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N4 C16 C15 110.8(4) . . ? N4 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? N4 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? N3 C17 H17A 109.5 . . ? N3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N3 C18 H18A 109.5 . . ? N3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N4 C19 H19A 109.5 . . ? N4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N4 C20 H20A 109.5 . . ? N4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O8 Cl1 O11A 132.0(6) . . ? O8 Cl1 O9A 112.4(7) . . ? O11A Cl1 O9A 114.5(6) . . ? O8 Cl1 O10A 61.4(5) . . ? O11A Cl1 O10A 109.9(5) . . ? O9A Cl1 O10A 110.2(5) . . ? O8 Cl1 O10 111.8(5) . . ? O11A Cl1 O10 79.4(5) . . ? O9A Cl1 O10 88.7(6) . . ? O10A Cl1 O10 50.5(5) . . ? O8 Cl1 O11 111.6(4) . . ? O11A Cl1 O11 28.2(5) . . ? O9A Cl1 O11 123.5(8) . . ? O10A Cl1 O11 121.3(7) . . ? O10 Cl1 O11 106.0(4) . . ? O8 Cl1 O9 112.1(4) . . ? O11A Cl1 O9 107.8(8) . . ? O9A Cl1 O9 21.1(7) . . ? O10A Cl1 O9 129.7(6) . . ? O10 Cl1 O9 107.5(4) . . ? O11 Cl1 O9 107.6(4) . . ? O8 Cl1 O8A 45.6(4) . . ? O11A Cl1 O8A 108.3(5) . . ? O9A Cl1 O8A 107.8(5) . . ? O10A Cl1 O8A 105.7(5) . . ? O10 Cl1 O8A 155.5(5) . . ? O11 Cl1 O8A 80.3(5) . . ? O9 Cl1 O8A 92.5(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 O7 Cu1 O1 C7 -11.7(3) . . . . ? O4 Cu1 O1 C7 82.9(3) 2_556 . . . ? N2 Cu1 O1 C7 170.3(3) . . . . ? N1 Cu1 O1 C7 -104.3(3) . . . . ? O7 Cu2 O2 C7 29.3(3) . . . . ? O3 Cu2 O2 C7 -64.1(3) 2_556 . . . ? N4 Cu2 O2 C7 -152.1(3) . . . . ? N3 Cu2 O2 C7 121.5(3) . . . . ? O4 Cu1 O7 Cu2 -58.40(15) 2_556 . . . ? N2 Cu1 O7 Cu2 -146.3(5) . . . . ? N1 Cu1 O7 Cu2 140.47(15) . . . . ? O1 Cu1 O7 Cu2 43.12(15) . . . . ? O3 Cu2 O7 Cu1 54.19(14) 2_556 . . . ? N4 Cu2 O7 Cu1 141.0(7) . . . . ? N3 Cu2 O7 Cu1 -143.82(15) . . . . ? O2 Cu2 O7 Cu1 -47.97(15) . . . . ? O7 Cu1 N1 C11 -81.4(3) . . . . ? O4 Cu1 N1 C11 176.5(4) 2_556 . . . ? N2 Cu1 N1 C11 110.7(3) . . . . ? O1 Cu1 N1 C11 18.5(3) . . . . ? O7 Cu1 N1 C9 158.7(3) . . . . ? O4 Cu1 N1 C9 56.6(5) 2_556 . . . ? N2 Cu1 N1 C9 -9.2(3) . . . . ? O1 Cu1 N1 C9 -101.4(3) . . . . ? O7 Cu1 N1 C12 38.8(3) . . . . ? O4 Cu1 N1 C12 -63.3(5) 2_556 . . . ? N2 Cu1 N1 C12 -129.1(3) . . . . ? O1 Cu1 N1 C12 138.7(3) . . . . ? O7 Cu1 N2 C14 148.0(5) . . . . ? O4 Cu1 N2 C14 59.4(3) 2_556 . . . ? N1 Cu1 N2 C14 -138.2(3) . . . . ? O1 Cu1 N2 C14 -41.4(3) . . . . ? O7 Cu1 N2 C10 -92.5(6) . . . . ? O4 Cu1 N2 C10 178.9(3) 2_556 . . . ? N1 Cu1 N2 C10 -18.6(3) . . . . ? O1 Cu1 N2 C10 78.2(3) . . . . ? O7 Cu1 N2 C13 26.7(7) . . . . ? O4 Cu1 N2 C13 -61.9(3) 2_556 . . . ? N1 Cu1 N2 C13 100.6(3) . . . . ? O1 Cu1 N2 C13 -162.6(3) . . . . ? O7 Cu2 N3 C15 -162.9(3) . . . . ? O3 Cu2 N3 C15 -62.3(6) 2_556 . . . ? N4 Cu2 N3 C15 8.6(3) . . . . ? O2 Cu2 N3 C15 99.9(3) . . . . ? O7 Cu2 N3 C17 76.5(3) . . . . ? O3 Cu2 N3 C17 177.1(3) 2_556 . . . ? N4 Cu2 N3 C17 -112.0(3) . . . . ? O2 Cu2 N3 C17 -20.7(3) . . . . ? O7 Cu2 N3 C18 -41.2(3) . . . . ? O3 Cu2 N3 C18 59.4(5) 2_556 . . . ? N4 Cu2 N3 C18 130.3(3) . . . . ? O2 Cu2 N3 C18 -138.4(3) . . . . ? O7 Cu2 N4 C19 -27.8(10) . . . . ? O3 Cu2 N4 C19 59.3(3) 2_556 . . . ? N3 Cu2 N4 C19 -103.4(3) . . . . ? O2 Cu2 N4 C19 161.1(3) . . . . ? O7 Cu2 N4 C20 -148.7(7) . . . . ? O3 Cu2 N4 C20 -61.6(3) 2_556 . . . ? N3 Cu2 N4 C20 135.7(3) . . . . ? O2 Cu2 N4 C20 40.2(3) . . . . ? O7 Cu2 N4 C16 93.0(8) . . . . ? O3 Cu2 N4 C16 -179.9(3) 2_556 . . . ? N3 Cu2 N4 C16 17.4(3) . . . . ? O2 Cu2 N4 C16 -78.1(3) . . . . ? C6 C1 C2 C3 -2.0(5) . . . . ? C7 C1 C2 C3 -178.6(3) . . . . ? C1 C2 C3 C4 2.2(5) . . . . ? C1 C2 C3 C8 178.6(3) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? C8 C3 C4 C5 -176.7(3) . . . . ? C3 C4 C5 C6 -2.1(6) . . . . ? C3 C4 C5 N5 174.7(3) . . . . ? O5 N5 C5 C6 175.1(4) . . . . ? O6 N5 C5 C6 -5.0(6) . . . . ? O5 N5 C5 C4 -1.8(6) . . . . ? O6 N5 C5 C4 178.1(4) . . . . ? C4 C5 C6 C1 2.3(6) . . . . ? N5 C5 C6 C1 -174.5(3) . . . . ? C2 C1 C6 C5 -0.3(5) . . . . ? C7 C1 C6 C5 176.5(3) . . . . ? Cu2 O2 C7 O1 -0.4(6) . . . . ? Cu2 O2 C7 C1 177.7(2) . . . . ? Cu1 O1 C7 O2 -10.1(6) . . . . ? Cu1 O1 C7 C1 171.8(2) . . . . ? C2 C1 C7 O2 -1.2(5) . . . . ? C6 C1 C7 O2 -177.8(3) . . . . ? C2 C1 C7 O1 177.1(3) . . . . ? C6 C1 C7 O1 0.5(5) . . . . ? Cu2 O3 C8 O4 -20.4(6) 2_546 . . . ? Cu2 O3 C8 C3 159.7(3) 2_546 . . . ? Cu1 O4 C8 O3 13.3(6) 2_546 . . . ? Cu1 O4 C8 C3 -166.8(2) 2_546 . . . ? C2 C3 C8 O3 141.2(4) . . . . ? C4 C3 C8 O3 -42.4(5) . . . . ? C2 C3 C8 O4 -38.7(5) . . . . ? C4 C3 C8 O4 137.7(4) . . . . ? C11 N1 C9 C10 -84.6(5) . . . . ? C12 N1 C9 C10 157.0(4) . . . . ? Cu1 N1 C9 C10 35.3(4) . . . . ? C14 N2 C10 C9 166.3(4) . . . . ? C13 N2 C10 C9 -74.5(5) . . . . ? Cu1 N2 C10 C9 43.3(4) . . . . ? N1 C9 C10 N2 -54.0(5) . . . . ? C17 N3 C15 C16 86.8(5) . . . . ? C18 N3 C15 C16 -157.3(4) . . . . ? Cu2 N3 C15 C16 -33.5(5) . . . . ? C19 N4 C16 C15 79.2(5) . . . . ? C20 N4 C16 C15 -162.0(4) . . . . ? Cu2 N4 C16 C15 -40.6(5) . . . . ? N3 C15 C16 N4 51.9(7) . . . . ? 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 O7 H7A O9 0.970(11) 2.39(3) 3.178(6) 138(3) 4_666 O7 H7A O9A 0.970(11) 2.37(3) 3.151(7) 137(3) 4_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.471 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.065 data_compound-4 _database_code_depnum_ccdc_archive 'CCDC 838925' #TrackingRef '17722_web_deposit_cif_file_0_SergioMartinez-Vargas_1360785764.articleADG.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ; catena-(Diaqua-(mu-5-aminoisophtalato-O,O'')-bis-(N,N,N',N'- tetramethylethylendia ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H38 Cu2 N5 O5, 0.5(Cl2 O8)' _chemical_formula_sum 'C20 H38 Cl Cu2 N5 O9' _chemical_formula_weight 655.08 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.4967(15) _cell_length_b 15.6562(9) _cell_length_c 15.3494(9) _cell_angle_alpha 90.00 _cell_angle_beta 120.4730(10) _cell_angle_gamma 90.00 _cell_volume 5695.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 6825 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 30.91 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2720 _exptl_absorpt_coefficient_mu 1.641 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.6571 _exptl_absorpt_correction_T_max 0.8648 _exptl_absorpt_process_details 'SHELXTL V 6.12 (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 291(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 AXS CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 0.83 _diffrn_reflns_number 23495 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0665 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.37 _reflns_number_total 5148 _reflns_number_gt 3301 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 6.23A (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0450P)^2^] 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 5148 _refine_ls_number_parameters 470 _refine_ls_number_restraints 361 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_restrained_S_all 0.932 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.341037(19) 0.04909(3) 0.18819(4) 0.03555(15) Uani 1 1 d . . . Cu2 Cu 0.22972(2) -0.05688(3) 0.02365(3) 0.03692(15) Uani 1 1 d . . . O1 O 0.19756(11) 0.04113(17) 0.0774(2) 0.0452(7) Uani 1 1 d . . . O2 O 0.27073(11) 0.12725(16) 0.1675(2) 0.0455(7) Uani 1 1 d . . . O3 O 0.33747(12) -0.05365(16) 0.2598(2) 0.0448(7) Uani 1 1 d . . . O4 O 0.26511(12) -0.13317(16) 0.1435(2) 0.0487(8) Uani 1 1 d . . . O5 O 0.30232(12) -0.00799(17) 0.0584(2) 0.0450(7) Uani 1 1 d D . . H5 H 0.3229(15) -0.0511(17) 0.069(3) 0.054 Uiso 1 1 d D . . N1 N 0.37748(16) 0.1375(2) 0.1367(3) 0.0524(10) Uani 1 1 d . . . N2 N 0.39376(14) 0.1023(2) 0.3290(3) 0.0423(9) Uani 1 1 d . . . N3 N 0.15798(15) -0.1316(2) -0.0291(3) 0.0479(9) Uani 1 1 d . . . N4 N 0.19262(15) -0.0137(2) -0.1245(2) 0.0477(9) Uani 1 1 d . . . N5 N 0.02944(18) 0.1982(3) 0.0458(4) 0.0814(15) Uani 1 1 d D . . H5A H 0.013(2) 0.162(3) -0.005(3) 0.098 Uiso 1 1 d D . . H5B H 0.009(2) 0.225(3) 0.067(4) 0.098 Uiso 1 1 d D . . C1 C 0.4231(2) 0.1815(4) 0.2282(4) 0.0849(18) Uani 1 1 d . . . H1A H 0.4581 0.1499 0.2536 0.102 Uiso 1 1 calc R . . H1B H 0.4289 0.2383 0.2098 0.102 Uiso 1 1 calc R . . C2 C 0.4089(2) 0.1880(3) 0.3074(4) 0.0755(16) Uani 1 1 d . . . H2A H 0.3774 0.2268 0.2861 0.091 Uiso 1 1 calc R . . H2B H 0.4409 0.2108 0.3683 0.091 Uiso 1 1 calc R . . C3 C 0.3344(2) 0.2002(3) 0.0707(4) 0.0831(18) Uani 1 1 d . . . H3A H 0.3515 0.2430 0.0501 0.125 Uiso 1 1 calc R . . H3B H 0.3184 0.2267 0.1070 0.125 Uiso 1 1 calc R . . H3C H 0.3051 0.1717 0.0121 0.125 Uiso 1 1 calc R . . C4 C 0.4021(2) 0.0975(4) 0.0803(4) 0.0831(18) Uani 1 1 d . . . H4A H 0.3724 0.0750 0.0175 0.125 Uiso 1 1 calc R . . H4B H 0.4270 0.0520 0.1199 0.125 Uiso 1 1 calc R . . H4C H 0.4230 0.1395 0.0670 0.125 Uiso 1 1 calc R . . C5 C 0.3664(2) 0.1137(3) 0.3886(3) 0.0653(14) Uani 1 1 d . . . H5D H 0.3504 0.0604 0.3926 0.098 Uiso 1 1 calc R . . H5E H 0.3371 0.1557 0.3569 0.098 Uiso 1 1 calc R . . H5F H 0.3938 0.1324 0.4554 0.098 Uiso 1 1 calc R . . C6 C 0.44413(19) 0.0486(3) 0.3898(4) 0.0722(15) Uani 1 1 d . . . H6A H 0.4631 0.0387 0.3526 0.108 Uiso 1 1 calc R . . H6B H 0.4328 -0.0051 0.4042 0.108 Uiso 1 1 calc R . . H6C H 0.4692 0.0773 0.4520 0.108 Uiso 1 1 calc R . . C7 C 0.1153(2) -0.0913(3) -0.1262(4) 0.0658(14) Uani 1 1 d . . . H7A H 0.0844 -0.1308 -0.1641 0.079 Uiso 1 1 calc R . . H7B H 0.1002 -0.0404 -0.1124 0.079 Uiso 1 1 calc R . . C8 C 0.1417(2) -0.0685(3) -0.1863(4) 0.0658(14) Uani 1 1 d . . . H8A H 0.1148 -0.0379 -0.2466 0.079 Uiso 1 1 calc R . . H8B H 0.1527 -0.1200 -0.2069 0.079 Uiso 1 1 calc R . . C9 C 0.1705(2) -0.2210(3) -0.0446(4) 0.0663(15) Uani 1 1 d . . . H9A H 0.1972 -0.2458 0.0194 0.099 Uiso 1 1 calc R . . H9B H 0.1862 -0.2210 -0.0880 0.099 Uiso 1 1 calc R . . H9C H 0.1364 -0.2539 -0.0752 0.099 Uiso 1 1 calc R . . C10 C 0.1353(2) -0.1326(3) 0.0403(4) 0.0677(15) Uani 1 1 d . . . H10A H 0.1027 -0.1690 0.0131 0.102 Uiso 1 1 calc R . . H10B H 0.1249 -0.0757 0.0476 0.102 Uiso 1 1 calc R . . H10C H 0.1636 -0.1538 0.1052 0.102 Uiso 1 1 calc R . . C11 C 0.2297(2) -0.0209(3) -0.1672(4) 0.0753(16) Uani 1 1 d . . . H11A H 0.2104 0.0002 -0.2353 0.113 Uiso 1 1 calc R . . H11B H 0.2397 -0.0798 -0.1671 0.113 Uiso 1 1 calc R . . H11C H 0.2634 0.0120 -0.1271 0.113 Uiso 1 1 calc R . . C12 C 0.1770(2) 0.0775(3) -0.1304(4) 0.0730(16) Uani 1 1 d . . . H12A H 0.1635 0.0982 -0.1978 0.110 Uiso 1 1 calc R . . H12B H 0.2095 0.1099 -0.0836 0.110 Uiso 1 1 calc R . . H12C H 0.1479 0.0835 -0.1138 0.110 Uiso 1 1 calc R . . C13 C 0.18070(16) 0.1713(2) 0.1350(3) 0.0303(9) Uani 1 1 d . . . C14 C 0.20378(16) 0.2426(2) 0.1972(3) 0.0340(9) Uani 1 1 d . . . H14 H 0.2426 0.2513 0.2329 0.041 Uiso 1 1 calc R . . C15 C 0.16757(17) 0.3008(2) 0.2049(3) 0.0355(10) Uani 1 1 d . . . C16 C 0.10982(17) 0.2863(3) 0.1529(3) 0.0417(10) Uani 1 1 d . . . H16 H 0.0859 0.3257 0.1573 0.050 Uiso 1 1 calc R . . C17 C 0.08740(17) 0.2130(3) 0.0938(3) 0.0430(10) Uani 1 1 d . . . C18 C 0.12336(16) 0.1571(2) 0.0849(3) 0.0369(10) Uani 1 1 d . . . H18 H 0.1086 0.1090 0.0443 0.044 Uiso 1 1 calc R . . C19 C 0.21959(18) 0.1084(2) 0.1256(3) 0.0343(9) Uani 1 1 d . . . C20 C 0.19031(18) 0.3774(3) 0.2732(3) 0.0379(10) Uani 1 1 d . . . Cl1 Cl -0.0159(7) 0.3624(12) 0.2260(13) 0.076(3) Uani 0.273(10) 1 d PDU A -1 O6 O -0.0114(7) 0.3542(12) 0.1373(10) 0.088(4) Uani 0.273(10) 1 d PDU A -1 O7 O -0.0738(7) 0.3838(11) 0.1922(17) 0.081(4) Uani 0.273(10) 1 d PDU A -1 O9 O -0.0001(10) 0.2877(11) 0.2829(16) 0.104(5) Uani 0.273(10) 1 d PDU A -1 O8 O 0.0178(8) 0.4345(9) 0.2815(13) 0.127(6) Uani 0.273(10) 1 d PDU A -1 Cl1A Cl -0.0114(9) 0.3622(14) 0.2345(15) 0.079(3) Uani 0.227(10) 1 d PDU A -2 O6A O 0.0310(8) 0.4176(14) 0.2374(16) 0.095(5) Uani 0.227(10) 1 d PDU A -2 O7A O 0.0106(11) 0.3275(13) 0.3340(19) 0.083(5) Uani 0.227(10) 1 d PDU A -2 O8A O -0.0618(8) 0.4062(16) 0.203(2) 0.086(5) Uani 0.227(10) 1 d PDU A -2 O9A O -0.0193(12) 0.2935(13) 0.167(2) 0.096(6) Uani 0.227(10) 1 d PDU A -2 Cl2 Cl 0.4920(2) 0.4092(3) 0.2870(5) 0.088(2) Uani 0.345(4) 1 d PDU B -1 O11 O 0.4606(5) 0.3940(9) 0.1826(8) 0.120(3) Uani 0.345(4) 1 d PDU B -1 O12 O 0.5373(5) 0.3536(8) 0.3328(10) 0.130(5) Uani 0.345(4) 1 d PDU B -1 O13 O 0.4576(5) 0.3939(8) 0.3339(10) 0.128(3) Uani 0.345(4) 1 d PDU B -1 O14 O 0.5040(5) 0.4974(5) 0.3020(9) 0.133(4) Uani 0.345(4) 1 d PDU B -1 Cl2A Cl 0.5046(6) 0.4283(10) 0.1733(12) 0.117(4) Uani 0.155(4) 1 d PDU B -2 O11A O 0.5016(10) 0.4763(14) 0.0917(14) 0.120(3) Uani 0.155(4) 1 d PDU B -2 O12A O 0.5169(11) 0.4850(16) 0.2527(17) 0.128(6) Uani 0.155(4) 1 d PDU B -2 O13A O 0.5486(10) 0.3665(14) 0.211(2) 0.128(3) Uani 0.155(4) 1 d PDU B -2 O14A O 0.4532(9) 0.3836(19) 0.136(2) 0.133(4) Uani 0.155(4) 1 d PDU 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 0.0358(3) 0.0311(3) 0.0414(3) 0.0025(2) 0.0208(2) -0.0018(2) Cu2 0.0396(3) 0.0337(3) 0.0357(3) -0.0017(2) 0.0179(2) 0.0012(2) O1 0.0453(17) 0.0424(18) 0.0494(19) -0.0167(14) 0.0253(15) -0.0039(14) O2 0.0343(18) 0.0424(17) 0.056(2) -0.0070(14) 0.0198(16) 0.0043(13) O3 0.0554(18) 0.0318(16) 0.0413(17) 0.0021(13) 0.0203(15) -0.0107(14) O4 0.0433(18) 0.0396(17) 0.047(2) 0.0093(14) 0.0113(16) -0.0078(14) O5 0.0497(19) 0.0429(19) 0.0451(18) -0.0001(14) 0.0260(16) 0.0000(14) N1 0.059(3) 0.048(2) 0.057(3) 0.0066(19) 0.034(2) -0.0117(19) N2 0.037(2) 0.039(2) 0.047(2) 0.0028(16) 0.0176(19) -0.0038(16) N3 0.041(2) 0.042(2) 0.050(2) -0.0032(17) 0.016(2) -0.0012(17) N4 0.053(2) 0.054(2) 0.036(2) -0.0016(17) 0.023(2) 0.0050(19) N5 0.034(3) 0.093(4) 0.101(4) -0.040(3) 0.022(3) -0.005(2) C1 0.088(4) 0.083(4) 0.092(5) -0.009(3) 0.052(4) -0.046(3) C2 0.083(4) 0.057(3) 0.076(4) -0.016(3) 0.034(3) -0.035(3) C3 0.098(5) 0.063(4) 0.102(5) 0.042(3) 0.060(4) 0.010(3) C4 0.092(4) 0.098(4) 0.094(5) 0.002(3) 0.074(4) -0.009(4) C5 0.070(4) 0.077(4) 0.049(3) -0.015(3) 0.030(3) -0.002(3) C6 0.042(3) 0.085(4) 0.060(4) -0.004(3) 0.004(3) 0.002(3) C7 0.042(3) 0.070(3) 0.063(4) -0.007(3) 0.011(3) -0.005(3) C8 0.057(3) 0.084(4) 0.042(3) -0.006(3) 0.014(3) -0.004(3) C9 0.060(3) 0.045(3) 0.082(4) -0.020(3) 0.028(3) -0.005(2) C10 0.060(3) 0.070(4) 0.082(4) -0.007(3) 0.043(3) -0.016(3) C11 0.083(4) 0.107(4) 0.048(3) -0.007(3) 0.042(3) -0.005(3) C12 0.096(4) 0.062(3) 0.052(3) 0.015(3) 0.030(3) 0.020(3) C13 0.034(2) 0.029(2) 0.029(2) 0.0031(17) 0.0166(19) 0.0020(17) C14 0.029(2) 0.034(2) 0.038(2) 0.0017(19) 0.016(2) 0.0019(18) C15 0.043(3) 0.031(2) 0.033(2) 0.0037(17) 0.019(2) 0.0043(19) C16 0.036(3) 0.042(3) 0.048(3) 0.001(2) 0.021(2) 0.012(2) C17 0.031(2) 0.046(3) 0.046(3) -0.004(2) 0.015(2) -0.003(2) C18 0.039(3) 0.032(2) 0.039(3) -0.0079(18) 0.020(2) -0.0048(19) C19 0.041(3) 0.037(2) 0.027(2) 0.0047(18) 0.019(2) 0.004(2) C20 0.039(3) 0.036(2) 0.044(3) -0.004(2) 0.025(2) 0.001(2) Cl1 0.091(5) 0.065(4) 0.102(6) -0.008(3) 0.072(5) -0.015(3) O6 0.099(8) 0.098(9) 0.099(8) 0.012(6) 0.073(7) 0.007(7) O7 0.094(6) 0.065(9) 0.115(9) -0.010(7) 0.075(7) -0.011(6) O9 0.127(8) 0.098(6) 0.095(10) 0.017(6) 0.062(9) 0.005(6) O8 0.115(10) 0.107(7) 0.121(10) -0.032(7) 0.032(10) -0.034(8) Cl1A 0.093(6) 0.065(4) 0.105(6) -0.010(4) 0.070(6) -0.011(4) O6A 0.097(8) 0.097(8) 0.123(10) 0.001(7) 0.078(8) -0.017(7) O7A 0.106(9) 0.078(10) 0.106(8) -0.010(7) 0.084(8) 0.001(9) O8A 0.089(8) 0.068(10) 0.119(10) -0.017(8) 0.066(9) -0.012(7) O9A 0.115(9) 0.086(8) 0.104(10) -0.019(7) 0.068(9) 0.002(7) Cl2 0.045(3) 0.058(3) 0.106(5) 0.005(3) -0.003(3) -0.012(2) O11 0.087(7) 0.086(7) 0.117(5) -0.006(5) 0.000(5) -0.012(5) O12 0.125(8) 0.115(9) 0.094(8) -0.034(8) 0.014(6) 0.067(8) O13 0.084(5) 0.115(7) 0.148(8) 0.023(6) 0.031(6) 0.004(5) O14 0.081(5) 0.068(4) 0.150(9) 0.004(5) -0.016(7) -0.024(4) Cl2A 0.068(6) 0.093(8) 0.119(8) -0.018(5) -0.004(7) -0.009(5) O11A 0.087(7) 0.086(7) 0.117(5) -0.006(5) 0.000(5) -0.012(5) O12A 0.085(12) 0.104(10) 0.104(8) -0.019(8) -0.020(9) -0.016(7) O13A 0.084(5) 0.115(7) 0.148(8) 0.023(6) 0.031(6) 0.004(5) O14A 0.081(5) 0.068(4) 0.150(9) 0.004(5) -0.016(7) -0.024(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O5 1.937(3) . ? Cu1 O3 1.979(3) . ? Cu1 N2 2.070(3) . ? Cu1 N1 2.085(3) . ? Cu1 O2 2.171(3) . ? Cu2 O5 1.943(3) . ? Cu2 O4 1.985(3) . ? Cu2 N3 2.073(3) . ? Cu2 N4 2.077(3) . ? Cu2 O1 2.135(3) . ? O1 C19 1.252(4) . ? O2 C19 1.249(4) . ? O3 C20 1.269(4) 4_545 ? O4 C20 1.256(5) 4_545 ? O5 H5 0.843(10) . ? N1 C3 1.475(6) . ? N1 C4 1.482(5) . ? N1 C1 1.495(6) . ? N2 C5 1.461(5) . ? N2 C6 1.478(5) . ? N2 C2 1.491(5) . ? N3 C10 1.482(6) . ? N3 C9 1.490(5) . ? N3 C7 1.491(6) . ? N4 C11 1.471(5) . ? N4 C12 1.481(5) . ? N4 C8 1.498(6) . ? N5 C17 1.395(6) . ? N5 H5A 0.88(2) . ? N5 H5B 0.89(2) . ? C1 C2 1.456(7) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5D 0.9600 . ? C5 H5E 0.9600 . ? C5 H5F 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.480(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C18 1.377(5) . ? C13 C14 1.395(5) . ? C13 C19 1.514(5) . ? C14 C15 1.397(5) . ? C14 H14 0.9300 . ? C15 C16 1.387(5) . ? C15 C20 1.505(5) . ? C16 C17 1.397(5) . ? C16 H16 0.9300 . ? C17 C18 1.378(5) . ? C18 H18 0.9300 . ? C20 O4 1.256(5) 4 ? C20 O3 1.269(4) 4 ? Cl1 O9 1.39(2) . ? Cl1 O8 1.434(10) . ? Cl1 O6 1.435(11) . ? Cl1 O7 1.441(12) . ? Cl1A O8A 1.40(2) . ? Cl1A O7A 1.434(12) . ? Cl1A O9A 1.434(12) . ? Cl1A O6A 1.435(10) . ? Cl2 O12 1.383(8) . ? Cl2 O11 1.402(8) . ? Cl2 O14 1.412(8) . ? Cl2 O13 1.469(8) . ? Cl2A O12A 1.403(8) . ? Cl2A O14A 1.412(9) . ? Cl2A O13A 1.424(9) . ? Cl2A O11A 1.427(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cu1 O3 92.32(11) . . ? O5 Cu1 N2 171.08(13) . . ? O3 Cu1 N2 87.29(12) . . ? O5 Cu1 N1 92.02(13) . . ? O3 Cu1 N1 156.79(14) . . ? N2 Cu1 N1 84.94(14) . . ? O5 Cu1 O2 97.20(11) . . ? O3 Cu1 O2 104.37(11) . . ? N2 Cu1 O2 91.52(12) . . ? N1 Cu1 O2 97.68(13) . . ? O5 Cu2 O4 91.73(11) . . ? O5 Cu2 N3 166.26(13) . . ? O4 Cu2 N3 86.82(13) . . ? O5 Cu2 N4 92.18(13) . . ? O4 Cu2 N4 161.39(13) . . ? N3 Cu2 N4 85.08(14) . . ? O5 Cu2 O1 100.38(11) . . ? O4 Cu2 O1 100.29(11) . . ? N3 Cu2 O1 93.32(12) . . ? N4 Cu2 O1 96.88(12) . . ? C19 O1 Cu2 131.4(3) . . ? C19 O2 Cu1 128.9(3) . . ? C20 O3 Cu1 131.2(3) 4_545 . ? C20 O4 Cu2 129.1(2) 4_545 . ? Cu1 O5 Cu2 114.58(14) . . ? Cu1 O5 H5 102(3) . . ? Cu2 O5 H5 104(3) . . ? C3 N1 C4 109.1(4) . . ? C3 N1 C1 109.8(4) . . ? C4 N1 C1 109.2(4) . . ? C3 N1 Cu1 109.2(3) . . ? C4 N1 Cu1 113.0(3) . . ? C1 N1 Cu1 106.6(3) . . ? C5 N2 C6 106.8(4) . . ? C5 N2 C2 108.7(4) . . ? C6 N2 C2 112.0(4) . . ? C5 N2 Cu1 113.1(3) . . ? C6 N2 Cu1 111.5(3) . . ? C2 N2 Cu1 104.9(3) . . ? C10 N3 C9 108.7(4) . . ? C10 N3 C7 108.5(4) . . ? C9 N3 C7 111.5(4) . . ? C10 N3 Cu2 112.9(3) . . ? C9 N3 Cu2 109.9(3) . . ? C7 N3 Cu2 105.2(3) . . ? C11 N4 C12 106.9(4) . . ? C11 N4 C8 108.1(4) . . ? C12 N4 C8 111.4(4) . . ? C11 N4 Cu2 113.4(3) . . ? C12 N4 Cu2 110.3(3) . . ? C8 N4 Cu2 106.8(3) . . ? C17 N5 H5A 121(4) . . ? C17 N5 H5B 120(4) . . ? H5A N5 H5B 119(5) . . ? C2 C1 N1 111.3(4) . . ? C2 C1 H1A 109.4 . . ? N1 C1 H1A 109.4 . . ? C2 C1 H1B 109.4 . . ? N1 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? C1 C2 N2 110.3(4) . . ? C1 C2 H2A 109.6 . . ? N2 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? N2 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 H5D 109.5 . . ? N2 C5 H5E 109.5 . . ? H5D C5 H5E 109.5 . . ? N2 C5 H5F 109.5 . . ? H5D C5 H5F 109.5 . . ? H5E C5 H5F 109.5 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 N3 109.7(4) . . ? C8 C7 H7A 109.7 . . ? N3 C7 H7A 109.7 . . ? C8 C7 H7B 109.7 . . ? N3 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C7 C8 N4 109.9(4) . . ? C7 C8 H8A 109.7 . . ? N4 C8 H8A 109.7 . . ? C7 C8 H8B 109.7 . . ? N4 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N3 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 120.4(3) . . ? C18 C13 C19 120.4(3) . . ? C14 C13 C19 119.2(3) . . ? C13 C14 C15 118.9(4) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C16 C15 C14 120.1(4) . . ? C16 C15 C20 118.8(4) . . ? C14 C15 C20 121.1(4) . . ? C15 C16 C17 120.5(4) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 N5 121.8(4) . . ? C18 C17 C16 118.9(4) . . ? N5 C17 C16 119.3(4) . . ? C13 C18 C17 121.2(4) . . ? C13 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? O2 C19 O1 125.7(4) . . ? O2 C19 C13 117.5(3) . . ? O1 C19 C13 116.7(4) . . ? O4 C20 O3 126.7(4) 4 4 ? O4 C20 C15 116.7(3) 4 . ? O3 C20 C15 116.5(4) 4 . ? O9 Cl1 O8 112.7(10) . . ? O9 Cl1 O6 111.8(10) . . ? O8 Cl1 O6 107.1(9) . . ? O9 Cl1 O7 111.0(9) . . ? O8 Cl1 O7 107.1(10) . . ? O6 Cl1 O7 106.9(10) . . ? O8A Cl1A O7A 111.3(10) . . ? O8A Cl1A O9A 111.2(10) . . ? O7A Cl1A O9A 108.3(12) . . ? O8A Cl1A O6A 111.2(12) . . ? O7A Cl1A O6A 107.4(11) . . ? O9A Cl1A O6A 107.4(11) . . ? O12 Cl2 O11 110.4(6) . . ? O12 Cl2 O14 117.2(8) . . ? O11 Cl2 O14 108.0(6) . . ? O12 Cl2 O13 106.6(6) . . ? O11 Cl2 O13 110.8(8) . . ? O14 Cl2 O13 103.6(6) . . ? O12A Cl2A O14A 114.6(9) . . ? O12A Cl2A O13A 107.4(7) . . ? O14A Cl2A O13A 107.4(7) . . ? O12A Cl2A O11A 108.1(7) . . ? O14A Cl2A O11A 107.8(7) . . ? O13A Cl2A O11A 111.6(9) . . ? 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 O5 Cu2 O1 C19 -5.4(4) . . . . ? O4 Cu2 O1 C19 88.3(3) . . . . ? N3 Cu2 O1 C19 175.7(3) . . . . ? N4 Cu2 O1 C19 -98.9(3) . . . . ? O5 Cu1 O2 C19 38.3(3) . . . . ? O3 Cu1 O2 C19 -55.9(3) . . . . ? N2 Cu1 O2 C19 -143.5(3) . . . . ? N1 Cu1 O2 C19 131.4(3) . . . . ? O5 Cu1 O3 C20 -12.3(4) . . . 4_545 ? N2 Cu1 O3 C20 176.6(4) . . . 4_545 ? N1 Cu1 O3 C20 -112.9(4) . . . 4_545 ? O2 Cu1 O3 C20 85.8(4) . . . 4_545 ? O5 Cu2 O4 C20 27.7(4) . . . 4_545 ? N3 Cu2 O4 C20 -166.0(4) . . . 4_545 ? N4 Cu2 O4 C20 129.7(4) . . . 4_545 ? O1 Cu2 O4 C20 -73.2(4) . . . 4_545 ? O3 Cu1 O5 Cu2 55.22(15) . . . . ? N2 Cu1 O5 Cu2 142.5(7) . . . . ? N1 Cu1 O5 Cu2 -147.58(16) . . . . ? O2 Cu1 O5 Cu2 -49.58(15) . . . . ? O4 Cu2 O5 Cu1 -60.78(15) . . . . ? N3 Cu2 O5 Cu1 -144.5(5) . . . . ? N4 Cu2 O5 Cu1 137.41(16) . . . . ? O1 Cu2 O5 Cu1 40.01(16) . . . . ? O5 Cu1 N1 C3 75.1(3) . . . . ? O3 Cu1 N1 C3 175.8(3) . . . . ? N2 Cu1 N1 C3 -113.3(3) . . . . ? O2 Cu1 N1 C3 -22.4(3) . . . . ? O5 Cu1 N1 C4 -46.4(3) . . . . ? O3 Cu1 N1 C4 54.3(5) . . . . ? N2 Cu1 N1 C4 125.2(3) . . . . ? O2 Cu1 N1 C4 -144.0(3) . . . . ? O5 Cu1 N1 C1 -166.4(3) . . . . ? O3 Cu1 N1 C1 -65.7(5) . . . . ? N2 Cu1 N1 C1 5.2(3) . . . . ? O2 Cu1 N1 C1 96.1(3) . . . . ? O5 Cu1 N2 C5 -150.7(7) . . . . ? O3 Cu1 N2 C5 -63.0(3) . . . . ? N1 Cu1 N2 C5 138.9(3) . . . . ? O2 Cu1 N2 C5 41.3(3) . . . . ? O5 Cu1 N2 C6 -30.3(10) . . . . ? O3 Cu1 N2 C6 57.4(3) . . . . ? N1 Cu1 N2 C6 -100.7(3) . . . . ? O2 Cu1 N2 C6 161.7(3) . . . . ? O5 Cu1 N2 C2 91.0(8) . . . . ? O3 Cu1 N2 C2 178.7(3) . . . . ? N1 Cu1 N2 C2 20.6(3) . . . . ? O2 Cu1 N2 C2 -77.0(3) . . . . ? O5 Cu2 N3 C10 144.0(5) . . . . ? O4 Cu2 N3 C10 59.8(3) . . . . ? N4 Cu2 N3 C10 -137.0(3) . . . . ? O1 Cu2 N3 C10 -40.4(3) . . . . ? O5 Cu2 N3 C9 22.4(7) . . . . ? O4 Cu2 N3 C9 -61.9(3) . . . . ? N4 Cu2 N3 C9 101.4(3) . . . . ? O1 Cu2 N3 C9 -162.0(3) . . . . ? O5 Cu2 N3 C7 -97.8(6) . . . . ? O4 Cu2 N3 C7 177.9(3) . . . . ? N4 Cu2 N3 C7 -18.8(3) . . . . ? O1 Cu2 N3 C7 77.8(3) . . . . ? O5 Cu2 N4 C11 39.2(3) . . . . ? O4 Cu2 N4 C11 -62.8(6) . . . . ? N3 Cu2 N4 C11 -127.3(3) . . . . ? O1 Cu2 N4 C11 139.9(3) . . . . ? O5 Cu2 N4 C12 -80.7(3) . . . . ? O4 Cu2 N4 C12 177.2(4) . . . . ? N3 Cu2 N4 C12 112.7(3) . . . . ? O1 Cu2 N4 C12 20.0(3) . . . . ? O5 Cu2 N4 C8 158.1(3) . . . . ? O4 Cu2 N4 C8 56.1(5) . . . . ? N3 Cu2 N4 C8 -8.4(3) . . . . ? O1 Cu2 N4 C8 -101.2(3) . . . . ? C3 N1 C1 C2 86.2(5) . . . . ? C4 N1 C1 C2 -154.3(5) . . . . ? Cu1 N1 C1 C2 -32.0(5) . . . . ? N1 C1 C2 N2 52.9(6) . . . . ? C5 N2 C2 C1 -165.9(4) . . . . ? C6 N2 C2 C1 76.4(5) . . . . ? Cu1 N2 C2 C1 -44.6(5) . . . . ? C10 N3 C7 C8 165.1(4) . . . . ? C9 N3 C7 C8 -75.2(5) . . . . ? Cu2 N3 C7 C8 44.0(4) . . . . ? N3 C7 C8 N4 -54.4(5) . . . . ? C11 N4 C8 C7 157.5(4) . . . . ? C12 N4 C8 C7 -85.3(5) . . . . ? Cu2 N4 C8 C7 35.2(5) . . . . ? C18 C13 C14 C15 -2.2(5) . . . . ? C19 C13 C14 C15 179.5(3) . . . . ? C13 C14 C15 C16 1.2(6) . . . . ? C13 C14 C15 C20 178.2(3) . . . . ? C14 C15 C16 C17 1.1(6) . . . . ? C20 C15 C16 C17 -176.0(4) . . . . ? C15 C16 C17 C18 -2.5(6) . . . . ? C15 C16 C17 N5 177.2(4) . . . . ? C14 C13 C18 C17 0.7(6) . . . . ? C19 C13 C18 C17 179.1(3) . . . . ? N5 C17 C18 C13 -178.1(4) . . . . ? C16 C17 C18 C13 1.6(6) . . . . ? Cu1 O2 C19 O1 -7.4(6) . . . . ? Cu1 O2 C19 C13 171.4(2) . . . . ? Cu2 O1 C19 O2 -11.8(6) . . . . ? Cu2 O1 C19 C13 169.3(2) . . . . ? C18 C13 C19 O2 175.5(3) . . . . ? C14 C13 C19 O2 -6.1(5) . . . . ? C18 C13 C19 O1 -5.5(5) . . . . ? C14 C13 C19 O1 172.8(3) . . . . ? C16 C15 C20 O4 138.9(4) . . . 4 ? C14 C15 C20 O4 -38.2(5) . . . 4 ? C16 C15 C20 O3 -41.5(5) . . . 4 ? C14 C15 C20 O3 141.5(4) . . . 4 ? 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 N5 H5A O13 0.88(2) 2.32(3) 3.168(13) 162(5) 8_455 N5 H5A O11A 0.88(2) 2.47(4) 3.29(2) 156(5) 7 N5 H5A O13 0.88(2) 2.32(3) 3.168(13) 162(5) 8_455 N5 H5B O9A 0.89(2) 2.30(3) 3.16(2) 163(5) . N5 H5B O6 0.89(2) 2.48(4) 3.286(17) 150(5) . N5 H5B O7A 0.89(2) 2.45(3) 3.283(19) 156(5) 2 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.750 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.077 data_compound-1 _database_code_depnum_ccdc_archive 'CCDC 838926' #TrackingRef '17722_web_deposit_cif_file_0_SergioMartinez-Vargas_1360785764.articleADG.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-[Aqua-(\m-isophtalato-O,O")-N,N,N',N'-tetramethylethylen diamine)-copper(ii)] ; _chemical_name_common ; catena-(Aqua-(mu-isophtalato-O,O'')-N,N,N',N'- tetramethylethylen diamine)-copper(ii)) ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 Cu N2 O5' _chemical_formula_sum 'C14 H22 Cu N2 O5' _chemical_formula_weight 361.88 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' _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 6.8445(3) _cell_length_b 15.0636(8) _cell_length_c 16.1247(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.489(1) _cell_angle_gamma 90.00 _cell_volume 1644.3(1) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7829 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 24.98 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_min 0.232 _exptl_crystal_size_mid 0.302 _exptl_crystal_size_max 0.314 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 1.352 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.6991 _exptl_absorpt_correction_T_max 0.7747 _exptl_absorpt_process_details 'SHELXTL V 6.12 (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 293(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 AXS CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 0.661 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13205 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2893 _reflns_number_gt 2487 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 6.23C (Bruker, 1999)' _computing_structure_solution 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V 6.12 (Sheldrick, 2000)' _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^)+(0.0711P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2893 _refine_ls_number_parameters 209 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.007 _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 Cu Cu 0.09137(4) 0.952967(18) 0.259869(17) 0.02955(14) Uani 1 1 d . . . O1 O 0.2009(2) 0.86785(11) 0.34653(10) 0.0368(4) Uani 1 1 d . . . O2 O -0.0482(2) 0.81759(12) 0.40832(11) 0.0432(5) Uani 1 1 d . . . O3 O 0.1089(2) 0.86518(11) 0.16709(10) 0.0357(4) Uani 1 1 d . . . O4 O 0.4124(3) 0.91616(13) 0.20148(11) 0.0403(4) Uani 1 1 d . . . O5 O -0.2154(3) 0.93001(15) 0.29223(14) 0.0498(5) Uani 1 1 d D . . H5A H -0.178(4) 0.8888(14) 0.3270(15) 0.060 Uiso 1 1 d D . . H5B H -0.329(2) 0.922(2) 0.2659(17) 0.060 Uiso 1 1 d D . . N1 N 0.1838(4) 1.05694(13) 0.34159(15) 0.0406(6) Uani 1 1 d . . . N2 N -0.0085(4) 1.05177(13) 0.17622(15) 0.0421(6) Uani 1 1 d . . . C1 C 0.2782(3) 0.77581(14) 0.46301(14) 0.0283(5) Uani 1 1 d . . . C2 C 0.2196(3) 0.73199(14) 0.53179(14) 0.0285(5) Uani 1 1 d . . . H2 H 0.0880 0.7341 0.5399 0.034 Uiso 1 1 calc R . . C3 C 0.3546(3) 0.68555(15) 0.58788(14) 0.0296(5) Uani 1 1 d . . . C4 C 0.5526(4) 0.68460(17) 0.57640(16) 0.0364(6) Uani 1 1 d . . . H4 H 0.6454 0.6548 0.6144 0.044 Uiso 1 1 calc R . . C5 C 0.6107(4) 0.72785(17) 0.50869(17) 0.0396(6) Uani 1 1 d . . . H5 H 0.7426 0.7267 0.5009 0.048 Uiso 1 1 calc R . . C6 C 0.4740(4) 0.77295(16) 0.45227(16) 0.0344(6) Uani 1 1 d . . . H6 H 0.5147 0.8016 0.4067 0.041 Uiso 1 1 calc R . . C7 C 0.1285(4) 0.82416(15) 0.40186(14) 0.0298(5) Uani 1 1 d . . . C8 C 0.2903(4) 0.86786(15) 0.15786(14) 0.0313(5) Uani 1 1 d . . . C9 C 0.1302(5) 1.14103(18) 0.2952(2) 0.0594(9) Uani 1 1 d . . . H9A H 0.1013 1.1866 0.3342 0.071 Uiso 1 1 calc R . . H9B H 0.2408 1.1611 0.2688 0.071 Uiso 1 1 calc R . . C10 C -0.0422(6) 1.1275(2) 0.2313(2) 0.0784(12) Uani 1 1 d . . . H10A H -0.0673 1.1809 0.1978 0.094 Uiso 1 1 calc R . . H10B H -0.1573 1.1157 0.2582 0.094 Uiso 1 1 calc R . . C11 C 0.0840(6) 1.0536(2) 0.41638(19) 0.0595(9) Uani 1 1 d . . . H11A H 0.1323 1.1008 0.4539 0.071 Uiso 1 1 calc R . . H11B H 0.1105 0.9976 0.4441 0.071 Uiso 1 1 calc R . . H11C H -0.0558 1.0603 0.3999 0.071 Uiso 1 1 calc R . . C12 C 0.3992(5) 1.0518(2) 0.3677(2) 0.0632(10) Uani 1 1 d . . . H12A H 0.4415 1.1007 0.4041 0.076 Uiso 1 1 calc R . . H12B H 0.4647 1.0545 0.3191 0.076 Uiso 1 1 calc R . . H12C H 0.4315 0.9970 0.3968 0.076 Uiso 1 1 calc R . . C13 C -0.1981(6) 1.0325(2) 0.1252(2) 0.0756(12) Uani 1 1 d . . . H13A H -0.2323 1.0799 0.0860 0.091 Uiso 1 1 calc R . . H13B H -0.2981 1.0268 0.1608 0.091 Uiso 1 1 calc R . . H13C H -0.1885 0.9780 0.0952 0.091 Uiso 1 1 calc R . . C14 C 0.1338(6) 1.0745(3) 0.1208(2) 0.0789(12) Uani 1 1 d . . . H14A H 0.1325 1.0297 0.0785 0.095 Uiso 1 1 calc R . . H14B H 0.2635 1.0782 0.1528 0.095 Uiso 1 1 calc R . . H14C H 0.0992 1.1308 0.0947 0.095 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 Cu 0.0376(2) 0.0291(2) 0.0229(2) 0.00124(11) 0.00747(14) 0.00040(12) O1 0.0388(10) 0.0423(10) 0.0308(9) 0.0122(8) 0.0100(8) 0.0034(8) O2 0.0318(10) 0.0558(12) 0.0420(11) 0.0170(9) 0.0055(8) 0.0008(8) O3 0.0321(10) 0.0423(10) 0.0334(9) -0.0099(8) 0.0071(8) -0.0006(8) O4 0.0377(10) 0.0488(11) 0.0340(10) -0.0124(9) 0.0039(8) -0.0070(8) O5 0.0315(10) 0.0627(13) 0.0533(14) 0.0204(10) 0.0000(10) -0.0014(10) N1 0.0507(14) 0.0364(12) 0.0360(13) -0.0090(9) 0.0107(11) -0.0025(10) N2 0.0530(15) 0.0375(13) 0.0358(13) 0.0104(10) 0.0063(11) 0.0011(10) C1 0.0327(12) 0.0253(12) 0.0278(12) -0.0027(10) 0.0070(10) -0.0023(10) C2 0.0265(12) 0.0317(13) 0.0278(12) -0.0005(10) 0.0053(10) -0.0012(10) C3 0.0322(13) 0.0291(13) 0.0273(12) -0.0014(10) 0.0037(10) -0.0013(10) C4 0.0288(13) 0.0385(14) 0.0411(15) 0.0030(12) 0.0026(11) 0.0007(10) C5 0.0294(13) 0.0429(15) 0.0487(17) 0.0033(12) 0.0129(12) -0.0009(11) C6 0.0366(14) 0.0349(14) 0.0336(14) 0.0032(11) 0.0114(11) -0.0035(11) C7 0.0394(14) 0.0279(12) 0.0222(12) -0.0022(10) 0.0051(11) -0.0038(10) C8 0.0363(14) 0.0322(13) 0.0247(12) 0.0008(10) 0.0020(10) 0.0011(11) C9 0.080(2) 0.0326(16) 0.066(2) -0.0063(15) 0.0130(18) -0.0066(15) C10 0.121(3) 0.042(2) 0.072(3) 0.0058(17) 0.012(2) 0.022(2) C11 0.083(2) 0.058(2) 0.0433(19) -0.0173(14) 0.0278(18) -0.0035(16) C12 0.055(2) 0.062(2) 0.070(2) -0.0279(17) -0.0010(18) -0.0081(15) C13 0.065(2) 0.079(2) 0.077(3) 0.041(2) -0.012(2) -0.0053(18) C14 0.082(3) 0.089(3) 0.072(3) 0.046(2) 0.030(2) 0.014(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 Cu O1 1.9620(16) . ? Cu O3 2.0135(16) . ? Cu N2 2.056(2) . ? Cu N1 2.084(2) . ? Cu O5 2.263(2) . ? O1 C7 1.267(3) . ? O2 C7 1.233(3) . ? O3 C8 1.273(3) . ? O4 C8 1.245(3) . ? N1 C11 1.472(4) . ? N1 C12 1.474(4) . ? N1 C9 1.489(4) . ? N2 C13 1.460(4) . ? N2 C14 1.456(4) . ? N2 C10 1.484(4) . ? C1 C6 1.377(3) . ? C1 C2 1.399(3) . ? C1 C7 1.502(3) . ? C2 C3 1.383(3) . ? C3 C4 1.395(3) . ? C3 C8 1.504(3) 4_576 ? C4 C5 1.379(3) . ? C5 C6 1.383(3) . ? C8 C3 1.504(3) 4_575 ? C9 C10 1.462(5) . ? 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 O1 Cu O3 92.39(7) . . ? O1 Cu N2 174.34(8) . . ? O3 Cu N2 92.21(8) . . ? O1 Cu N1 89.57(9) . . ? O3 Cu N1 156.58(9) . . ? N2 Cu N1 84.91(10) . . ? O1 Cu O5 90.33(7) . . ? O3 Cu O5 103.29(8) . . ? N2 Cu O5 91.84(9) . . ? N1 Cu O5 100.03(9) . . ? C7 O1 Cu 133.88(16) . . ? C8 O3 Cu 103.42(14) . . ? C11 N1 C12 109.3(3) . . ? C11 N1 C9 109.3(2) . . ? C12 N1 C9 110.5(2) . . ? C11 N1 Cu 111.01(18) . . ? C12 N1 Cu 109.78(17) . . ? C9 N1 Cu 107.01(18) . . ? C13 N2 C14 108.7(3) . . ? C13 N2 C10 106.6(3) . . ? C14 N2 C10 111.3(3) . . ? C13 N2 Cu 114.04(17) . . ? C14 N2 Cu 112.7(2) . . ? C10 N2 Cu 103.28(18) . . ? C6 C1 C2 118.9(2) . . ? C6 C1 C7 121.0(2) . . ? C2 C1 C7 120.1(2) . . ? C3 C2 C1 121.0(2) . . ? C2 C3 C4 119.1(2) . . ? C2 C3 C8 121.3(2) . 4_576 ? C4 C3 C8 119.5(2) . 4_576 ? C5 C4 C3 120.0(2) . . ? C4 C5 C6 120.4(2) . . ? C1 C6 C5 120.6(2) . . ? O2 C7 O1 126.3(2) . . ? O2 C7 C1 119.2(2) . . ? O1 C7 C1 114.5(2) . . ? O4 C8 O3 122.5(2) . . ? O4 C8 C3 119.4(2) . 4_575 ? O3 C8 C3 118.0(2) . 4_575 ? C10 C9 N1 110.4(2) . . ? C9 C10 N2 110.4(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 O5 H5A O2 0.851(10) 1.819(12) 2.655(3) 167(3) . O5 H5B O4 0.841(10) 1.915(11) 2.752(3) 174(3) 1_455 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.622 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.070 data_compound-6 _database_code_depnum_ccdc_archive 'CCDC 904860' #TrackingRef '17722_web_deposit_cif_file_0_SergioMartinez-Vargas_1360785764.articleADG.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ; catena-(Aqua-(mu-Tetrafluoroisophtalato-O,O'')-(N,N,N',N'- tetramethylethylendiami ; _chemical_melting_point ? _chemical_formula_moiety ; C14 H16 Cu F4 N2 O4, 0.5(C28 H36 Cu2 F8 N4 O10), 3(H2 O) ; _chemical_formula_sum 'C28 H40 Cu2 F8 N4 O12' _chemical_formula_weight 903.72 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' F F 0.0171 0.0103 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 13.3966(8) _cell_length_b 11.9465(7) _cell_length_c 24.1319(14) _cell_angle_alpha 90.00 _cell_angle_beta 100.3820(10) _cell_angle_gamma 90.00 _cell_volume 3798.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6400 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 30.79 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1848 _exptl_absorpt_coefficient_mu 1.220 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.6753 _exptl_absorpt_correction_T_max 0.7868 _exptl_absorpt_process_details 'SHELXTL V 6.12 (Sheldrick, 2000)' _exptl_special_details ? _diffrn_ambient_temperature 298(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 AXS CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 0.83 _diffrn_reflns_number 30542 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.03 _reflns_number_total 6706 _reflns_number_gt 4859 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 6.23A (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V 6.12 (Sheldrick, 2000)' _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^)+(0.0480P)^2^] 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 6706 _refine_ls_number_parameters 582 _refine_ls_number_restraints 146 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0830 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_restrained_S_all 0.918 _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 0.75449(2) 0.68945(3) 0.118039(13) 0.04405(11) Uani 1 1 d . . . F1 F 0.81636(14) 0.93727(13) 0.25690(6) 0.0699(5) Uani 1 1 d . . . F2 F 0.97389(14) 0.86733(16) 0.44271(7) 0.0797(5) Uani 1 1 d . . . F3 F 1.01854(18) 0.65848(18) 0.41497(8) 0.1070(8) Uani 1 1 d . . . F4 F 0.96427(16) 0.58711(15) 0.30758(8) 0.0906(6) Uani 1 1 d . . . O1 O 0.76619(16) 0.73740(15) 0.19689(7) 0.0539(5) Uani 1 1 d . . . O2 O 0.92228(16) 0.68430(17) 0.19319(9) 0.0666(6) Uani 1 1 d . . . O3 O 0.76895(15) 1.03521(15) 0.36211(7) 0.0526(5) Uani 1 1 d . . . O4 O 0.92739(17) 1.09521(18) 0.38123(10) 0.0793(7) Uani 1 1 d . . . C1 C 0.8889(2) 0.7608(2) 0.27878(12) 0.0487(7) Uani 1 1 d . . . C2 C 0.8666(2) 0.8666(2) 0.29586(11) 0.0499(7) Uani 1 1 d . . . C3 C 0.8942(2) 0.9078(2) 0.34977(12) 0.0497(7) Uani 1 1 d . . . C4 C 0.9470(2) 0.8352(3) 0.38884(13) 0.0578(8) Uani 1 1 d . . . C5 C 0.9698(2) 0.7284(3) 0.37469(14) 0.0663(9) Uani 1 1 d . . . C6 C 0.9419(2) 0.6932(2) 0.32009(13) 0.0600(8) Uani 1 1 d . . . C7 C 0.8585(2) 0.7234(2) 0.21806(12) 0.0512(7) Uani 1 1 d . . . C8 C 0.8632(2) 1.0232(2) 0.36566(11) 0.0534(7) Uani 1 1 d . . . N1 N 0.77876(19) 0.6466(2) 0.04079(9) 0.0582(6) Uani 1 1 d DU . . C9 C 0.7593(11) 0.7520(6) 0.0068(4) 0.090(2) Uani 0.573(16) 1 d PDU A 1 H9A H 0.8234 0.7788 -0.0015 0.108 Uiso 0.573(16) 1 calc PR A 1 H9B H 0.7160 0.7341 -0.0288 0.108 Uiso 0.573(16) 1 calc PR A 1 C10 C 0.7155(11) 0.8359(6) 0.0317(4) 0.089(3) Uani 0.573(16) 1 d PDU A 1 H10A H 0.6426 0.8257 0.0224 0.107 Uiso 0.573(16) 1 calc PR A 1 H10B H 0.7309 0.9057 0.0145 0.107 Uiso 0.573(16) 1 calc PR A 1 C9A C 0.8109(12) 0.7524(7) 0.0162(5) 0.077(2) Uani 0.427(16) 1 d PDU A 2 H9C H 0.8837 0.7598 0.0283 0.092 Uiso 0.427(16) 1 calc PR A 2 H9D H 0.7986 0.7437 -0.0244 0.092 Uiso 0.427(16) 1 calc PR A 2 C10A C 0.7694(14) 0.8459(6) 0.0275(5) 0.083(3) Uani 0.427(16) 1 d PDU A 2 H10C H 0.7079 0.8577 0.0001 0.099 Uiso 0.427(16) 1 calc PR A 2 H10D H 0.8155 0.9070 0.0239 0.099 Uiso 0.427(16) 1 calc PR A 2 N2 N 0.7417(2) 0.8488(2) 0.09031(11) 0.0642(7) Uani 1 1 d DU . . C14 C 0.6518(5) 0.8988(5) 0.1106(5) 0.101(3) Uani 0.773(15) 1 d PDU A 1 H14A H 0.6678 0.9094 0.1507 0.152 Uiso 0.773(15) 1 calc PR A 1 H14B H 0.5947 0.8493 0.1016 0.152 Uiso 0.773(15) 1 calc PR A 1 H14C H 0.6354 0.9698 0.0925 0.152 Uiso 0.773(15) 1 calc PR A 1 C14A C 0.6320(8) 0.8740(19) 0.0735(12) 0.076(5) Uani 0.227(15) 1 d PDU A 2 H14D H 0.5966 0.8076 0.0587 0.114 Uiso 0.227(15) 1 calc PR A 2 H14E H 0.6228 0.9314 0.0452 0.114 Uiso 0.227(15) 1 calc PR A 2 H14F H 0.6057 0.8992 0.1058 0.114 Uiso 0.227(15) 1 calc PR A 2 C13 C 0.8248(3) 0.9225(3) 0.11371(15) 0.0896(12) Uani 1 1 d . A . H13A H 0.8144 0.9947 0.0962 0.134 Uiso 1 1 calc R . . H13B H 0.8875 0.8914 0.1069 0.134 Uiso 1 1 calc R . . H13C H 0.8273 0.9300 0.1536 0.134 Uiso 1 1 calc R . . C11 C 0.7043(3) 0.5692(4) 0.01035(15) 0.1147(16) Uani 1 1 d . A . H11A H 0.7159 0.5608 -0.0276 0.172 Uiso 1 1 calc R . . H11B H 0.6372 0.5982 0.0097 0.172 Uiso 1 1 calc R . . H11C H 0.7108 0.4978 0.0289 0.172 Uiso 1 1 calc R . . C12 C 0.8779(3) 0.5932(3) 0.04809(15) 0.0944(12) Uani 1 1 d . A . H12A H 0.8927 0.5729 0.0119 0.142 Uiso 1 1 calc R . . H12B H 0.8777 0.5272 0.0708 0.142 Uiso 1 1 calc R . . H12C H 0.9287 0.6442 0.0664 0.142 Uiso 1 1 calc R . . Cu2 Cu 0.07320(3) 0.22760(3) 0.152795(13) 0.04977(11) Uani 1 1 d . . . F5 F 0.01681(11) -0.09672(13) 0.02956(6) 0.0572(4) Uani 1 1 d . . . F6 F 0.29463(15) -0.24202(17) -0.03824(10) 0.0985(7) Uani 1 1 d . . . F7 F 0.42180(13) -0.1324(2) 0.04350(11) 0.1199(9) Uani 1 1 d . . . F8 F 0.34627(13) -0.00499(15) 0.11846(8) 0.0835(6) Uani 1 1 d . . . O5 O 0.15124(14) 0.13634(15) 0.10754(7) 0.0535(5) Uani 1 1 d . . . O6 O 0.08769(17) -0.00830(16) 0.14783(8) 0.0663(6) Uani 1 1 d . . . O7 O 0.04976(15) -0.19484(16) -0.09501(8) 0.0579(5) Uani 1 1 d . . . O8 O 0.0588(2) -0.33144(18) -0.03161(9) 0.0837(7) Uani 1 1 d . . . N4 N -0.0128(2) 0.2767(2) 0.20973(10) 0.0647(7) Uani 1 1 d . . . C15 C 0.1792(2) -0.0432(2) 0.07443(10) 0.0414(6) Uani 1 1 d . . . C16 C 0.11837(18) -0.1030(2) 0.03266(10) 0.0399(6) Uani 1 1 d . . . C17 C 0.1529(2) -0.1700(2) -0.00632(10) 0.0427(6) Uani 1 1 d . . . C18 C 0.2555(2) -0.1780(2) -0.00144(13) 0.0579(8) Uani 1 1 d . . . C19 C 0.3209(2) -0.1227(3) 0.04031(15) 0.0658(9) Uani 1 1 d . . . C20 C 0.2818(2) -0.0566(2) 0.07760(12) 0.0524(7) Uani 1 1 d . . . C21 C 0.1352(2) 0.0330(2) 0.11381(11) 0.0497(7) Uani 1 1 d . . . C22 C 0.0805(2) -0.2387(2) -0.04812(12) 0.0512(7) Uani 1 1 d . . . N3 N 0.1956(2) 0.2500(2) 0.21522(10) 0.0625(7) Uani 1 1 d DU . . C23 C 0.1566(5) 0.3296(6) 0.2534(3) 0.0837(18) Uani 0.737(10) 1 d PDU B 1 H23A H 0.1487 0.4033 0.2364 0.100 Uiso 0.737(10) 1 calc PR B 1 H23B H 0.2041 0.3352 0.2888 0.100 Uiso 0.737(10) 1 calc PR B 1 C24 C 0.0553(4) 0.2875(7) 0.2640(3) 0.0819(18) Uani 0.737(10) 1 d PDU B 1 H24A H 0.0636 0.2155 0.2829 0.098 Uiso 0.737(10) 1 calc PR B 1 H24B H 0.0271 0.3397 0.2879 0.098 Uiso 0.737(10) 1 calc PR B 1 C23A C 0.1609(12) 0.2765(17) 0.2687(4) 0.077(3) Uani 0.263(10) 1 d PDU B 2 H23C H 0.2125 0.3188 0.2935 0.093 Uiso 0.263(10) 1 calc PR B 2 H23D H 0.1477 0.2080 0.2878 0.093 Uiso 0.263(10) 1 calc PR B 2 C24A C 0.0647(12) 0.3447(16) 0.2541(6) 0.079(3) Uani 0.263(10) 1 d PDU B 2 H24C H 0.0794 0.4163 0.2383 0.095 Uiso 0.263(10) 1 calc PR B 2 H24D H 0.0362 0.3585 0.2876 0.095 Uiso 0.263(10) 1 calc PR B 2 C25 C 0.2358(3) 0.1429(3) 0.23966(16) 0.1071(15) Uani 1 1 d . B . H25A H 0.2666 0.1028 0.2127 0.161 Uiso 1 1 calc R . . H25B H 0.1814 0.0992 0.2494 0.161 Uiso 1 1 calc R . . H25C H 0.2856 0.1568 0.2729 0.161 Uiso 1 1 calc R . . C26 C 0.2780(3) 0.3105(4) 0.19575(18) 0.1165(16) Uani 1 1 d . B . H26A H 0.3333 0.3206 0.2267 0.175 Uiso 1 1 calc R . . H26B H 0.2538 0.3823 0.1813 0.175 Uiso 1 1 calc R . . H26C H 0.3008 0.2683 0.1666 0.175 Uiso 1 1 calc R . . C27 C -0.0771(3) 0.3742(3) 0.19138(16) 0.0997(13) Uani 1 1 d . B . H27A H -0.1197 0.3894 0.2185 0.150 Uiso 1 1 calc R . . H27B H -0.1185 0.3588 0.1554 0.150 Uiso 1 1 calc R . . H27C H -0.0350 0.4381 0.1882 0.150 Uiso 1 1 calc R . . C28 C -0.0809(4) 0.1830(3) 0.21864(17) 0.1137(16) Uani 1 1 d . B . H28A H -0.0410 0.1177 0.2307 0.170 Uiso 1 1 calc R . . H28B H -0.1263 0.1669 0.1840 0.170 Uiso 1 1 calc R . . H28C H -0.1195 0.2036 0.2469 0.170 Uiso 1 1 calc R . . O9 O 0.0949(2) 0.39834(19) 0.11021(11) 0.0891(8) Uani 1 1 d D . . H9E H 0.128(3) 0.457(2) 0.1065(18) 0.134 Uiso 1 1 d D . . H9F H 0.045(2) 0.396(4) 0.0834(13) 0.134 Uiso 1 1 d D . . O10 O 0.16363(19) 0.61019(18) 0.08289(10) 0.0701(6) Uani 1 1 d D . . H10E H 0.140(3) 0.651(3) 0.1065(12) 0.105 Uiso 1 1 d D . . H10F H 0.136(3) 0.621(3) 0.0491(7) 0.105 Uiso 1 1 d D . . O11 O 0.08617(18) -0.24075(19) 0.14989(11) 0.0752(6) Uani 1 1 d D . . H11D H 0.042(2) -0.262(3) 0.1688(15) 0.113 Uiso 1 1 d D . . H11E H 0.081(3) -0.1706(9) 0.1497(17) 0.113 Uiso 1 1 d D . . O12 O 1.1277(3) 1.0545(5) 0.35910(19) 0.1192(18) Uani 0.768(6) 1 d PDU C 1 H12D H 1.078(4) 1.072(7) 0.375(3) 0.179 Uiso 0.768(6) 1 d PD C 1 H12E H 1.179(4) 1.088(6) 0.378(3) 0.179 Uiso 0.768(6) 1 d PD C 1 O12A O 1.1282(11) 1.1670(18) 0.3798(6) 0.122(4) Uani 0.232(6) 1 d PDU C 2 H12F H 1.080(9) 1.17(2) 0.398(6) 0.183 Uiso 0.232(6) 1 d PD C 2 H12G H 1.185(7) 1.16(2) 0.402(6) 0.183 Uiso 0.232(6) 1 d PD C 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 0.0497(2) 0.04309(19) 0.04063(19) 0.00630(14) 0.01151(15) -0.00167(15) F1 0.1071(14) 0.0511(10) 0.0507(10) 0.0000(8) 0.0122(9) 0.0158(9) F2 0.0783(13) 0.0935(14) 0.0596(11) -0.0222(10) -0.0081(10) 0.0153(10) F3 0.1298(18) 0.0990(15) 0.0756(13) -0.0075(11) -0.0259(13) 0.0601(14) F4 0.1168(16) 0.0641(12) 0.0844(13) -0.0144(10) 0.0003(12) 0.0423(11) O1 0.0634(13) 0.0576(12) 0.0421(11) -0.0026(9) 0.0136(10) 0.0025(10) O2 0.0725(14) 0.0667(14) 0.0704(14) -0.0205(11) 0.0386(12) -0.0085(11) O3 0.0582(13) 0.0449(11) 0.0560(12) -0.0081(9) 0.0137(10) 0.0060(9) O4 0.0673(15) 0.0670(15) 0.1041(18) -0.0300(13) 0.0163(13) -0.0116(12) C1 0.0479(16) 0.0499(17) 0.0507(17) -0.0069(13) 0.0153(13) 0.0034(13) C2 0.0551(18) 0.0473(17) 0.0488(17) -0.0020(13) 0.0134(14) 0.0058(13) C3 0.0457(16) 0.0497(17) 0.0549(18) -0.0091(14) 0.0123(14) 0.0024(13) C4 0.0479(17) 0.068(2) 0.0560(19) -0.0155(16) 0.0047(14) 0.0049(15) C5 0.060(2) 0.069(2) 0.065(2) -0.0038(17) -0.0023(17) 0.0215(16) C6 0.0613(19) 0.0494(18) 0.067(2) -0.0103(15) 0.0063(16) 0.0161(15) C7 0.064(2) 0.0393(15) 0.0552(18) -0.0039(13) 0.0246(16) -0.0059(14) C8 0.063(2) 0.0526(18) 0.0469(17) -0.0085(13) 0.0149(15) 0.0008(16) N1 0.0689(17) 0.0683(15) 0.0393(13) 0.0032(11) 0.0147(12) -0.0053(13) C9 0.106(6) 0.108(4) 0.062(4) 0.038(3) 0.030(4) 0.023(4) C10 0.132(7) 0.069(3) 0.064(4) 0.034(3) 0.011(5) -0.001(4) C9A 0.088(6) 0.099(4) 0.051(4) 0.028(3) 0.032(4) -0.005(4) C10A 0.114(7) 0.078(3) 0.058(4) 0.031(4) 0.022(5) -0.019(5) N2 0.0737(18) 0.0485(15) 0.0682(17) 0.0160(12) 0.0067(14) 0.0014(13) C14 0.083(4) 0.081(4) 0.134(7) 0.021(4) 0.002(4) 0.030(3) C14A 0.069(9) 0.074(9) 0.083(11) 0.020(9) 0.008(8) 0.024(7) C13 0.124(3) 0.055(2) 0.090(3) 0.0123(18) 0.020(2) -0.028(2) C11 0.103(3) 0.183(5) 0.057(2) -0.038(3) 0.011(2) -0.043(3) C12 0.081(3) 0.135(4) 0.072(2) -0.026(2) 0.028(2) 0.009(2) Cu2 0.0657(2) 0.0446(2) 0.03830(19) -0.00477(14) 0.00762(16) -0.00715(16) F5 0.0390(9) 0.0697(11) 0.0630(10) -0.0136(8) 0.0093(7) -0.0044(7) F6 0.0824(14) 0.1014(16) 0.1223(17) -0.0394(13) 0.0467(13) 0.0110(11) F7 0.0369(11) 0.145(2) 0.176(2) -0.0297(17) 0.0142(13) 0.0043(12) F8 0.0648(12) 0.0926(14) 0.0818(13) -0.0100(11) -0.0169(10) -0.0254(10) O5 0.0703(13) 0.0436(11) 0.0485(11) -0.0074(9) 0.0157(10) -0.0114(10) O6 0.0979(17) 0.0537(13) 0.0555(12) -0.0064(10) 0.0354(12) -0.0155(11) O7 0.0693(13) 0.0609(12) 0.0409(11) 0.0003(9) 0.0028(10) -0.0143(10) O8 0.129(2) 0.0533(14) 0.0605(14) 0.0046(11) -0.0056(13) -0.0346(13) N4 0.0784(18) 0.0687(17) 0.0470(15) -0.0090(12) 0.0107(13) 0.0089(15) C15 0.0484(16) 0.0383(15) 0.0372(14) 0.0036(11) 0.0070(12) -0.0073(12) C16 0.0361(15) 0.0426(15) 0.0406(14) 0.0050(11) 0.0062(12) -0.0002(11) C17 0.0509(17) 0.0365(14) 0.0412(15) 0.0007(11) 0.0096(12) -0.0028(12) C18 0.0539(19) 0.0537(18) 0.071(2) -0.0059(15) 0.0235(16) 0.0055(15) C19 0.0358(17) 0.070(2) 0.090(2) 0.0045(18) 0.0075(17) 0.0026(15) C20 0.0477(18) 0.0534(18) 0.0515(17) 0.0033(14) -0.0034(14) -0.0126(14) C21 0.0578(18) 0.0522(18) 0.0382(15) -0.0053(13) 0.0063(13) -0.0125(14) C22 0.0594(19) 0.0473(18) 0.0491(18) -0.0095(14) 0.0158(15) -0.0049(14) N3 0.0749(18) 0.0605(17) 0.0490(15) -0.0128(12) 0.0029(13) -0.0063(13) C23 0.107(3) 0.073(4) 0.063(3) -0.025(3) -0.006(3) 0.001(3) C24 0.108(4) 0.086(4) 0.050(3) -0.017(3) 0.010(3) 0.018(3) C23A 0.096(5) 0.078(6) 0.054(5) -0.017(5) 0.002(5) 0.010(5) C24A 0.102(6) 0.072(6) 0.057(5) -0.030(6) 0.000(5) 0.017(6) C25 0.136(4) 0.082(3) 0.081(3) -0.005(2) -0.040(3) 0.012(3) C26 0.090(3) 0.145(4) 0.104(3) 0.020(3) -0.009(3) -0.053(3) C27 0.118(3) 0.096(3) 0.086(3) -0.006(2) 0.020(2) 0.044(3) C28 0.151(4) 0.106(3) 0.106(3) 0.003(3) 0.083(3) -0.014(3) O9 0.117(2) 0.0593(15) 0.0786(17) 0.0201(13) -0.0162(14) -0.0312(14) O10 0.0798(16) 0.0563(14) 0.0727(16) 0.0054(12) 0.0101(13) 0.0011(11) O11 0.0771(16) 0.0619(14) 0.0939(18) 0.0092(13) 0.0351(13) 0.0007(13) O12 0.087(3) 0.172(5) 0.100(3) -0.012(3) 0.023(2) 0.000(3) O12A 0.080(7) 0.162(9) 0.123(8) 0.032(8) 0.015(6) -0.016(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 O3 1.9437(17) 2_645 ? Cu1 O1 1.9661(18) . ? Cu1 N1 2.015(2) . ? Cu1 N2 2.015(2) . ? F1 C2 1.350(3) . ? F2 C4 1.341(3) . ? F3 C5 1.356(3) . ? F4 C6 1.349(3) . ? O1 C7 1.261(3) . ? O2 C7 1.222(3) . ? O3 C8 1.259(3) . ? O3 Cu1 1.9436(17) 2_655 ? O4 C8 1.226(3) . ? C1 C6 1.377(4) . ? C1 C2 1.379(4) . ? C1 C7 1.516(4) . ? C2 C3 1.378(4) . ? C3 C4 1.379(4) . ? C3 C8 1.509(4) . ? C4 C5 1.370(4) . ? C5 C6 1.369(4) . ? N1 C12 1.456(4) . ? N1 C11 1.458(4) . ? N1 C9A 1.492(7) . ? N1 C9 1.499(6) . ? C9 C10 1.356(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N2 1.404(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C9A C10A 1.298(8) . ? C9A H9C 0.9700 . ? C9A H9D 0.9700 . ? C10A N2 1.624(13) . ? C10A H10C 0.9700 . ? C10A H10D 0.9700 . ? N2 C13 1.451(4) . ? N2 C14A 1.482(9) . ? N2 C14 1.503(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C14A H14D 0.9600 . ? C14A H14E 0.9600 . ? C14A H14F 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? Cu2 O5 1.9712(18) . ? Cu2 O7 1.9958(19) 3 ? Cu2 N4 2.032(2) . ? Cu2 N3 2.035(2) . ? Cu2 O9 2.326(2) . ? F5 C16 1.351(3) . ? F6 C18 1.348(3) . ? F7 C19 1.345(3) . ? F8 C20 1.338(3) . ? O5 C21 1.266(3) . ? O6 C21 1.230(3) . ? O7 C22 1.248(3) . ? O7 Cu2 1.9958(19) 3 ? O8 C22 1.230(3) . ? N4 C24 1.461(6) . ? N4 C27 1.468(4) . ? N4 C28 1.485(4) . ? N4 C24A 1.575(19) . ? C15 C20 1.372(4) . ? C15 C16 1.377(3) . ? C15 C21 1.510(4) . ? C16 C17 1.377(3) . ? C17 C18 1.362(4) . ? C17 C22 1.510(4) . ? C18 C19 1.378(4) . ? C19 C20 1.370(4) . ? N3 C26 1.466(4) . ? N3 C25 1.470(4) . ? N3 C23A 1.484(9) . ? N3 C23 1.484(5) . ? C23 C24 1.511(7) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C23A C24A 1.511(10) . ? C23A H23C 0.9700 . ? C23A H23D 0.9700 . ? C24A H24C 0.9700 . ? C24A H24D 0.9700 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? O9 H9E 0.844(10) . ? O9 H9F 0.846(10) . ? O10 H10E 0.850(10) . ? O10 H10F 0.844(10) . ? O11 H11D 0.844(10) . ? O11 H11E 0.841(10) . ? O12 H12D 0.852(11) . ? O12 H12E 0.851(11) . ? O12A H12D 1.31(8) . ? O12A H12E 1.17(8) . ? O12A H12F 0.852(11) . ? O12A H12G 0.853(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu1 O1 91.49(8) 2_645 . ? O3 Cu1 N1 92.72(9) 2_645 . ? O1 Cu1 N1 166.21(10) . . ? O3 Cu1 N2 165.85(10) 2_645 . ? O1 Cu1 N2 91.90(10) . . ? N1 Cu1 N2 87.19(11) . . ? C7 O1 Cu1 104.76(17) . . ? C8 O3 Cu1 107.21(17) . 2_655 ? C6 C1 C2 115.6(3) . . ? C6 C1 C7 122.7(2) . . ? C2 C1 C7 121.6(3) . . ? F1 C2 C3 116.7(2) . . ? F1 C2 C1 118.2(2) . . ? C3 C2 C1 125.0(3) . . ? C2 C3 C4 116.0(3) . . ? C2 C3 C8 121.8(3) . . ? C4 C3 C8 122.1(3) . . ? F2 C4 C5 118.4(3) . . ? F2 C4 C3 119.9(3) . . ? C5 C4 C3 121.7(3) . . ? F3 C5 C6 120.9(3) . . ? F3 C5 C4 119.7(3) . . ? C6 C5 C4 119.4(3) . . ? F4 C6 C5 118.1(3) . . ? F4 C6 C1 119.7(3) . . ? C5 C6 C1 122.2(3) . . ? O2 C7 O1 125.0(3) . . ? O2 C7 C1 119.8(3) . . ? O1 C7 C1 115.2(2) . . ? O4 C8 O3 125.5(3) . . ? O4 C8 C3 120.6(3) . . ? O3 C8 C3 113.9(3) . . ? C12 N1 C11 108.0(3) . . ? C12 N1 C9A 95.6(6) . . ? C11 N1 C9A 123.8(6) . . ? C12 N1 C9 119.9(6) . . ? C11 N1 C9 102.8(6) . . ? C9A N1 C9 26.6(5) . . ? C12 N1 Cu1 107.17(19) . . ? C11 N1 Cu1 114.7(2) . . ? C9A N1 Cu1 105.0(4) . . ? C9 N1 Cu1 104.6(4) . . ? C10 C9 N1 115.2(6) . . ? C10 C9 H9A 108.5 . . ? N1 C9 H9A 108.5 . . ? C10 C9 H9B 108.5 . . ? N1 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C9 C10 N2 118.5(6) . . ? C9 C10 H10A 107.7 . . ? N2 C10 H10A 107.7 . . ? C9 C10 H10B 107.7 . . ? N2 C10 H10B 107.7 . . ? H10A C10 H10B 107.1 . . ? C10A C9A N1 118.6(7) . . ? C10A C9A H9C 107.7 . . ? N1 C9A H9C 107.7 . . ? C10A C9A H9D 107.7 . . ? N1 C9A H9D 107.7 . . ? H9C C9A H9D 107.1 . . ? C9A C10A N2 113.2(7) . . ? C9A C10A H10C 108.9 . . ? N2 C10A H10C 108.9 . . ? C9A C10A H10D 108.9 . . ? N2 C10A H10D 108.9 . . ? H10C C10A H10D 107.7 . . ? C10 N2 C13 119.6(6) . . ? C10 N2 C14A 72.0(13) . . ? C13 N2 C14A 129.5(10) . . ? C10 N2 C14 107.6(7) . . ? C13 N2 C14 103.6(4) . . ? C14A N2 C14 36.5(9) . . ? C10 N2 C10A 27.7(6) . . ? C13 N2 C10A 95.0(6) . . ? C14A N2 C10A 97.6(13) . . ? C14 N2 C10A 130.1(7) . . ? C10 N2 Cu1 102.8(3) . . ? C13 N2 Cu1 115.5(2) . . ? C14A N2 Cu1 107.6(8) . . ? C14 N2 Cu1 107.0(3) . . ? C10A N2 Cu1 105.6(3) . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C14A H14D 109.5 . . ? N2 C14A H14E 109.5 . . ? H14D C14A H14E 109.5 . . ? N2 C14A H14F 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O5 Cu2 O7 87.59(8) . 3 ? O5 Cu2 N4 162.97(9) . . ? O7 Cu2 N4 91.83(9) 3 . ? O5 Cu2 N3 92.63(9) . . ? O7 Cu2 N3 175.35(9) 3 . ? N4 Cu2 N3 86.60(10) . . ? O5 Cu2 O9 96.86(9) . . ? O7 Cu2 O9 90.94(8) 3 . ? N4 Cu2 O9 100.17(11) . . ? N3 Cu2 O9 93.64(9) . . ? C21 O5 Cu2 110.78(17) . . ? C22 O7 Cu2 130.32(19) . 3 ? C24 N4 C27 116.0(4) . . ? C24 N4 C28 103.7(4) . . ? C27 N4 C28 107.4(3) . . ? C24 N4 C24A 28.0(6) . . ? C27 N4 C24A 94.3(6) . . ? C28 N4 C24A 129.6(8) . . ? C24 N4 Cu2 107.1(2) . . ? C27 N4 Cu2 113.5(2) . . ? C28 N4 Cu2 108.5(2) . . ? C24A N4 Cu2 102.9(5) . . ? C20 C15 C16 115.8(2) . . ? C20 C15 C21 122.4(2) . . ? C16 C15 C21 121.8(2) . . ? F5 C16 C15 118.0(2) . . ? F5 C16 C17 117.0(2) . . ? C15 C16 C17 125.1(2) . . ? C18 C17 C16 116.1(2) . . ? C18 C17 C22 122.5(2) . . ? C16 C17 C22 121.2(2) . . ? F6 C18 C17 119.2(3) . . ? F6 C18 C19 118.8(3) . . ? C17 C18 C19 121.9(3) . . ? F7 C19 C20 120.8(3) . . ? F7 C19 C18 120.0(3) . . ? C20 C19 C18 119.2(3) . . ? F8 C20 C19 118.5(3) . . ? F8 C20 C15 119.6(3) . . ? C19 C20 C15 121.9(3) . . ? O6 C21 O5 126.2(3) . . ? O6 C21 C15 119.1(2) . . ? O5 C21 C15 114.8(2) . . ? O8 C22 O7 127.9(3) . . ? O8 C22 C17 115.7(3) . . ? O7 C22 C17 116.4(2) . . ? C26 N3 C25 108.4(3) . . ? C26 N3 C23A 123.1(9) . . ? C25 N3 C23A 89.2(7) . . ? C26 N3 C23 104.7(3) . . ? C25 N3 C23 116.9(4) . . ? C23A N3 C23 28.5(6) . . ? C26 N3 Cu2 112.4(2) . . ? C25 N3 Cu2 111.7(2) . . ? C23A N3 Cu2 109.6(6) . . ? C23 N3 Cu2 102.5(3) . . ? N3 C23 C24 108.6(4) . . ? N3 C23 H23A 110.0 . . ? C24 C23 H23A 110.0 . . ? N3 C23 H23B 110.0 . . ? C24 C23 H23B 110.0 . . ? H23A C23 H23B 108.3 . . ? N4 C24 C23 108.2(6) . . ? N4 C24 H24A 110.1 . . ? C23 C24 H24A 110.1 . . ? N4 C24 H24B 110.1 . . ? C23 C24 H24B 110.1 . . ? H24A C24 H24B 108.4 . . ? N3 C23A C24A 107.4(8) . . ? N3 C23A H23C 110.2 . . ? C24A C23A H23C 110.2 . . ? N3 C23A H23D 110.2 . . ? C24A C23A H23D 110.2 . . ? H23C C23A H23D 108.5 . . ? C23A C24A N4 108.1(14) . . ? C23A C24A H24C 110.1 . . ? N4 C24A H24C 110.1 . . ? C23A C24A H24D 110.1 . . ? N4 C24A H24D 110.1 . . ? H24C C24A H24D 108.4 . . ? N3 C25 H25A 109.5 . . ? N3 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N3 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N3 C26 H26A 109.5 . . ? N3 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N3 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N4 C27 H27A 109.5 . . ? N4 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N4 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N4 C28 H28A 109.5 . . ? N4 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N4 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? Cu2 O9 H9E 152(3) . . ? Cu2 O9 H9F 99(3) . . ? H9E O9 H9F 108(4) . . ? H10E O10 H10F 114(4) . . ? H11D O11 H11E 103(4) . . ? H12D O12 H12E 106(8) . . ? H12D O12A H12E 66(2) . . ? H12D O12A H12F 72(10) . . ? H12E O12A H12F 126(10) . . ? H12D O12A H12G 111(10) . . ? H12E O12A H12G 60(10) . . ? H12F O12A H12G 110.2(19) . . ? 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 O9 H9E O10 0.844(10) 2.000(18) 2.812(3) 161(4) . O9 H9F O8 0.846(10) 1.857(19) 2.659(3) 158(4) 3 O10 H10E O11 0.850(10) 1.891(13) 2.733(3) 170(4) 1_565 O10 H10F O8 0.844(10) 2.109(12) 2.948(3) 173(4) 1_565 O11 H11D O2 0.844(10) 1.921(15) 2.746(3) 165(4) 1_445 O11 H11E O6 0.841(10) 1.942(12) 2.778(3) 172(4) . O12 H12D O4 0.852(11) 2.07(3) 2.870(5) 157(7) . O12 H12E O10 0.851(11) 2.16(3) 2.968(5) 157(8) 2_655 O12A H12F O4 0.852(11) 2.22(17) 2.830(14) 129(18) . O12A H12G O10 0.853(11) 2.09(9) 2.854(15) 149(17) 2_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.310 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.059 #==============================================================================