# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Castillo, Carmen' 'Manez, M. Angeles' 'Basallote, Manuel' 'Clares, Ma Paz' 'Blasco, Salvador' 'Garcia-Espana, Enrique' _publ_contact_author_name 'Basallote, Manuel' _publ_contact_author_email manuel.basallote@uca.es _publ_section_title ; Copper(II) Complexes of Quinoline Polyazamacrocyclic Scorpiand-Type Ligands: X-Ray, Equilibrium and Kinetic Studies ; # Attachment '- cupy2q_final.txt.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 864923' #TrackingRef '- cupy2q_final.txt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cu(pytren-2Q)]\^A.2CLO4\^A.H2O' _chemical_melting_point ? _chemical_formula_moiety 'C23 H30 Cu N6, 2(Cl O4), H2 O' _chemical_formula_sum 'C23 H32 Cl2 Cu N6 O9' _chemical_formula_weight 670.99 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' N N 0.0061 0.0033 '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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.222(1) _cell_length_b 10.4770(4) _cell_length_c 16.006(1) _cell_angle_alpha 90.00 _cell_angle_beta 103.110(3) _cell_angle_gamma 90.00 _cell_volume 2812.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8080 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description 'small leaves' _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1388 _exptl_absorpt_coefficient_mu 1.028 _exptl_absorpt_correction_type none _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_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11199 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_av_sigmaI/netI 0.1315 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6367 _reflns_number_gt 2562 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1507P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6367 _refine_ls_number_parameters 372 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1899 _refine_ls_R_factor_gt 0.0722 _refine_ls_wR_factor_ref 0.2687 _refine_ls_wR_factor_gt 0.1969 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.912 _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 0.22504(4) 0.22182(7) 0.02817(5) 0.0528(3) Uani 1 1 d . . . N1 N 0.3259(3) 0.1241(5) 0.0579(4) 0.0578(14) Uani 1 1 d . . . N2 N 0.2021(4) 0.0661(6) -0.0766(4) 0.0821(19) Uani 1 1 d . . . H2 H 0.1797 0.1010 -0.1285 0.098 Uiso 1 1 calc R . . N3 N 0.1640(3) 0.0824(5) 0.0919(4) 0.0637(15) Uani 1 1 d . . . N4 N 0.2720(4) 0.2810(5) 0.1673(4) 0.0752(17) Uani 1 1 d . . . H4 H 0.2626 0.3655 0.1738 0.090 Uiso 1 1 calc R . . N5 N 0.1196(4) 0.3058(6) 0.0006(5) 0.086(2) Uani 1 1 d . . . H5 H 0.0956 0.2708 -0.0509 0.104 Uiso 1 1 calc R . . N6 N 0.2545(3) 0.3903(5) -0.0376(3) 0.0575(14) Uani 1 1 d . . . C1 C 0.2800(6) 0.0132(8) -0.0773(7) 0.099(3) Uani 1 1 d . . . H1A H 0.3002 0.0544 -0.1223 0.118 Uiso 1 1 calc R . . H1B H 0.2742 -0.0770 -0.0907 0.118 Uiso 1 1 calc R . . C2 C 0.1468(5) -0.0247(7) -0.0512(6) 0.084(2) Uani 1 1 d . . . H2A H 0.1504 -0.1063 -0.0787 0.101 Uiso 1 1 calc R . . H2B H 0.0926 0.0065 -0.0702 0.101 Uiso 1 1 calc R . . C3 C 0.1662(5) -0.0424(6) 0.0463(5) 0.078(2) Uani 1 1 d . . . H3A H 0.1279 -0.1007 0.0616 0.093 Uiso 1 1 calc R . . H3B H 0.2188 -0.0800 0.0647 0.093 Uiso 1 1 calc R . . C4 C 0.2077(5) 0.0732(7) 0.1822(5) 0.076(2) Uani 1 1 d . . . H4A H 0.2557 0.0230 0.1857 0.092 Uiso 1 1 calc R . . H4B H 0.1749 0.0298 0.2151 0.092 Uiso 1 1 calc R . . C5 C 0.2302(6) 0.2040(7) 0.2205(5) 0.084(2) Uani 1 1 d . . . H5A H 0.1823 0.2485 0.2264 0.101 Uiso 1 1 calc R . . H5B H 0.2643 0.1942 0.2774 0.101 Uiso 1 1 calc R . . C6 C 0.3573(6) 0.2573(9) 0.1838(6) 0.094(3) Uani 1 1 d . . . H6A H 0.3771 0.2390 0.2443 0.113 Uiso 1 1 calc R . . H6B H 0.3839 0.3337 0.1705 0.113 Uiso 1 1 calc R . . C7 C 0.3771(4) 0.1486(8) 0.1322(6) 0.076(2) Uani 1 1 d . . . C8 C 0.4482(6) 0.0794(12) 0.1550(8) 0.125(4) Uani 1 1 d . . . H8 H 0.4858 0.1001 0.2046 0.150 Uiso 1 1 calc R . . C9 C 0.4621(8) -0.0182(16) 0.1043(11) 0.148(6) Uani 1 1 d . . . H9 H 0.5082 -0.0669 0.1210 0.177 Uiso 1 1 calc R . . C10 C 0.4092(8) -0.0452(9) 0.0296(11) 0.128(5) Uani 1 1 d . . . H10 H 0.4187 -0.1115 -0.0055 0.154 Uiso 1 1 calc R . . C11 C 0.3395(5) 0.0297(7) 0.0064(6) 0.077(2) Uani 1 1 d . . . C12 C 0.0804(4) 0.1281(8) 0.0821(6) 0.086(2) Uani 1 1 d . . . H12A H 0.0452 0.0763 0.0394 0.103 Uiso 1 1 calc R . . H12B H 0.0646 0.1175 0.1361 0.103 Uiso 1 1 calc R . . C13 C 0.0710(5) 0.2646(8) 0.0558(6) 0.086(2) Uani 1 1 d . . . H13A H 0.0157 0.2792 0.0274 0.103 Uiso 1 1 calc R . . H13B H 0.0826 0.3170 0.1070 0.103 Uiso 1 1 calc R . . C14 C 0.1231(5) 0.4372(6) -0.0185(6) 0.080(2) Uani 1 1 d . . . H14A H 0.1248 0.4862 0.0333 0.096 Uiso 1 1 calc R . . H14B H 0.0750 0.4609 -0.0600 0.096 Uiso 1 1 calc R . . C15 C 0.1940(5) 0.4709(6) -0.0535(5) 0.0671(19) Uani 1 1 d . . . C16 C 0.1933(6) 0.5864(7) -0.0977(5) 0.081(2) Uani 1 1 d . . . H16 H 0.1488 0.6394 -0.1077 0.097 Uiso 1 1 calc R . . C17 C 0.2588(6) 0.6184(7) -0.1250(5) 0.087(3) Uani 1 1 d . . . H17 H 0.2592 0.6942 -0.1551 0.105 Uiso 1 1 calc R . . C18 C 0.3255(5) 0.5413(6) -0.1096(5) 0.074(2) Uani 1 1 d . . . C19 C 0.3986(7) 0.5704(8) -0.1354(6) 0.093(3) Uani 1 1 d . . . H19 H 0.4025 0.6474 -0.1630 0.112 Uiso 1 1 calc R . . C20 C 0.4615(6) 0.4897(9) -0.1209(5) 0.095(3) Uani 1 1 d . . . H20 H 0.5074 0.5105 -0.1393 0.114 Uiso 1 1 calc R . . C21 C 0.4567(5) 0.3759(8) -0.0786(5) 0.083(2) Uani 1 1 d . . . H21 H 0.4998 0.3199 -0.0690 0.099 Uiso 1 1 calc R . . C22 C 0.3891(4) 0.3437(7) -0.0501(5) 0.0696(19) Uani 1 1 d . . . H22 H 0.3878 0.2676 -0.0206 0.084 Uiso 1 1 calc R . . C23 C 0.3230(5) 0.4243(6) -0.0651(4) 0.0651(18) Uani 1 1 d . . . Cl1 Cl 0.33259(16) 0.6558(2) 0.17672(16) 0.0923(7) Uani 1 1 d . . . O11 O 0.2704(8) 0.7225(12) 0.1868(11) 0.257(7) Uani 1 1 d . . . O12 O 0.3953(8) 0.7337(10) 0.1817(8) 0.222(6) Uani 1 1 d . . . O13 O 0.3524(6) 0.5801(11) 0.2489(8) 0.213(5) Uani 1 1 d . . . O14 O 0.3273(9) 0.5758(12) 0.1132(7) 0.261(7) Uani 1 1 d . . . Cl2 Cl -0.01140(12) 0.2092(2) 0.77854(16) 0.0878(7) Uani 1 1 d . . . O21 O -0.0553(5) 0.2844(6) 0.7157(5) 0.134(3) Uani 1 1 d . . . O22 O 0.0691(4) 0.2491(7) 0.8017(5) 0.121(2) Uani 1 1 d . . . O23 O -0.0416(7) 0.2133(14) 0.8504(8) 0.241(7) Uani 1 1 d . . . O24 O -0.0156(6) 0.0829(8) 0.7428(9) 0.228(6) Uani 1 1 d . . . O1 O 0.8479(5) 0.5001(7) 0.7872(5) 0.154(3) Uani 1 1 d D . . H1C H 0.8742(6) 0.4430(11) 0.7685(6) 0.185 Uiso 1 1 d RD . . H1D H 0.8165(7) 0.4418(12) 0.7949(6) 0.185 Uiso 1 1 d RD . . 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 0.0485(5) 0.0540(5) 0.0566(5) 0.0060(3) 0.0135(4) 0.0035(3) N1 0.052(3) 0.053(3) 0.070(4) 0.015(3) 0.018(3) 0.009(2) N2 0.094(5) 0.084(4) 0.070(4) -0.003(3) 0.022(4) -0.027(4) N3 0.059(4) 0.069(3) 0.067(4) 0.005(3) 0.023(3) -0.004(3) N4 0.091(5) 0.074(4) 0.058(4) -0.005(3) 0.010(4) -0.005(3) N5 0.059(4) 0.087(4) 0.116(6) 0.025(4) 0.026(4) 0.016(3) N6 0.060(4) 0.052(3) 0.055(4) 0.005(2) 0.001(3) 0.000(2) C1 0.124(8) 0.082(5) 0.107(8) -0.031(5) 0.064(7) -0.017(5) C2 0.085(6) 0.077(5) 0.089(7) -0.017(4) 0.014(5) -0.024(4) C3 0.077(5) 0.062(4) 0.094(7) 0.005(4) 0.020(5) -0.021(3) C4 0.077(5) 0.086(5) 0.071(6) 0.021(4) 0.030(4) -0.004(4) C5 0.096(6) 0.103(6) 0.053(5) 0.003(4) 0.017(4) -0.005(5) C6 0.082(7) 0.121(7) 0.072(6) 0.003(5) -0.002(5) -0.029(5) C7 0.048(5) 0.103(6) 0.077(6) 0.036(5) 0.016(4) -0.001(4) C8 0.054(6) 0.182(11) 0.135(10) 0.089(9) 0.016(6) 0.016(7) C9 0.105(10) 0.183(13) 0.170(15) 0.100(12) 0.062(10) 0.077(9) C10 0.117(9) 0.095(6) 0.205(14) 0.051(8) 0.104(10) 0.046(6) C11 0.067(5) 0.072(4) 0.107(7) 0.017(5) 0.047(5) 0.009(4) C12 0.059(5) 0.102(6) 0.105(7) 0.004(5) 0.036(5) -0.003(4) C13 0.060(5) 0.099(6) 0.101(7) 0.009(5) 0.025(5) 0.011(4) C14 0.071(5) 0.066(4) 0.098(6) 0.008(4) 0.010(5) 0.026(4) C15 0.082(5) 0.054(4) 0.060(5) 0.001(3) 0.006(4) 0.010(3) C16 0.110(7) 0.059(4) 0.068(5) 0.006(4) 0.006(5) 0.017(4) C17 0.144(9) 0.046(4) 0.067(6) 0.010(3) 0.013(6) 0.002(5) C18 0.114(7) 0.050(4) 0.057(5) 0.000(3) 0.017(4) -0.012(4) C19 0.128(8) 0.083(5) 0.072(6) 0.010(4) 0.028(6) -0.032(6) C20 0.110(8) 0.115(7) 0.069(6) 0.002(5) 0.042(6) -0.041(6) C21 0.084(6) 0.098(5) 0.073(6) 0.000(4) 0.032(5) -0.010(4) C22 0.063(5) 0.079(5) 0.068(5) 0.013(4) 0.017(4) -0.007(4) C23 0.081(5) 0.062(4) 0.049(4) -0.004(3) 0.009(4) -0.020(4) Cl1 0.1119(19) 0.0730(12) 0.0980(18) -0.0162(12) 0.0364(14) -0.0046(12) O11 0.223(14) 0.255(12) 0.297(16) -0.046(11) 0.066(11) 0.126(11) O12 0.290(16) 0.185(9) 0.229(13) -0.013(8) 0.139(12) -0.101(10) O13 0.173(9) 0.232(11) 0.218(11) 0.095(9) 0.008(8) -0.052(8) O14 0.391(19) 0.227(11) 0.151(9) -0.117(9) 0.031(10) 0.024(11) Cl2 0.0655(13) 0.1010(15) 0.0964(17) 0.0315(12) 0.0174(12) -0.0044(10) O21 0.134(6) 0.105(5) 0.136(6) 0.029(4) -0.027(5) 0.011(4) O22 0.075(4) 0.192(6) 0.098(5) 0.002(4) 0.025(4) -0.030(4) O23 0.156(9) 0.423(19) 0.174(10) 0.084(11) 0.097(8) -0.048(10) O24 0.167(9) 0.105(6) 0.368(18) -0.017(7) -0.032(9) 0.010(5) O1 0.174(8) 0.127(6) 0.179(8) -0.019(5) 0.080(6) 0.003(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 N5 1.975(6) . ? Cu1 N1 1.979(5) . ? Cu1 N6 2.174(5) . ? Cu1 N3 2.184(5) . ? Cu1 N4 2.276(6) . ? Cu1 N2 2.308(6) . ? N1 C7 1.335(10) . ? N1 C11 1.342(9) . ? N2 C1 1.454(10) . ? N2 C2 1.467(9) . ? N2 H2 0.9100 . ? N3 C4 1.474(9) . ? N3 C12 1.492(9) . ? N3 C3 1.502(9) . ? N4 C6 1.453(11) . ? N4 C5 1.474(10) . ? N4 H4 0.9100 . ? N5 C14 1.414(9) . ? N5 C13 1.417(10) . ? N5 H5 0.9100 . ? N6 C15 1.320(8) . ? N6 C23 1.394(8) . ? C1 C11 1.501(12) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.531(11) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.515(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.492(12) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.398(12) . ? C8 C9 1.360(18) . ? C8 H8 0.9300 . ? C9 C10 1.360(18) . ? C9 H9 0.9300 . ? C10 C11 1.411(13) . ? C10 H10 0.9300 . ? C12 C13 1.489(11) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.497(10) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.401(10) . ? C16 C17 1.341(11) . ? C16 H16 0.9300 . ? C17 C18 1.380(12) . ? C17 H17 0.9300 . ? C18 C23 1.424(9) . ? C18 C19 1.443(12) . ? C19 C20 1.352(12) . ? C19 H19 0.9300 . ? C20 C21 1.383(11) . ? C20 H20 0.9300 . ? C21 C22 1.386(10) . ? C21 H21 0.9300 . ? C22 C23 1.394(10) . ? C22 H22 0.9300 . ? Cl1 O14 1.304(8) . ? Cl1 O11 1.319(10) . ? Cl1 O12 1.341(10) . ? Cl1 O13 1.379(10) . ? Cl2 O21 1.364(7) . ? Cl2 O23 1.367(10) . ? Cl2 O22 1.414(7) . ? Cl2 O24 1.436(10) . ? O1 H1D 0.8442 . ? O1 H1C 0.8447 . ? 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 N5 Cu1 N1 175.1(2) . . ? N5 Cu1 N6 80.4(2) . . ? N1 Cu1 N6 104.3(2) . . ? N5 Cu1 N3 83.5(2) . . ? N1 Cu1 N3 91.8(2) . . ? N6 Cu1 N3 163.7(2) . . ? N5 Cu1 N4 101.7(3) . . ? N1 Cu1 N4 78.9(2) . . ? N6 Cu1 N4 100.5(2) . . ? N3 Cu1 N4 80.0(2) . . ? N5 Cu1 N2 98.9(3) . . ? N1 Cu1 N2 78.8(3) . . ? N6 Cu1 N2 104.0(2) . . ? N3 Cu1 N2 81.1(2) . . ? N4 Cu1 N2 150.2(2) . . ? C7 N1 C11 121.1(7) . . ? C7 N1 Cu1 118.7(5) . . ? C11 N1 Cu1 120.0(6) . . ? C1 N2 C2 114.4(7) . . ? C1 N2 Cu1 105.6(5) . . ? C2 N2 Cu1 105.8(5) . . ? C1 N2 H2 110.3 . . ? C2 N2 H2 110.3 . . ? Cu1 N2 H2 110.3 . . ? C4 N3 C12 113.0(6) . . ? C4 N3 C3 110.9(6) . . ? C12 N3 C3 111.0(6) . . ? C4 N3 Cu1 108.0(4) . . ? C12 N3 Cu1 106.9(4) . . ? C3 N3 Cu1 106.7(4) . . ? C6 N4 C5 114.0(6) . . ? C6 N4 Cu1 104.6(5) . . ? C5 N4 Cu1 107.7(4) . . ? C6 N4 H4 110.1 . . ? C5 N4 H4 110.1 . . ? Cu1 N4 H4 110.1 . . ? C14 N5 C13 119.4(7) . . ? C14 N5 Cu1 113.6(5) . . ? C13 N5 Cu1 111.6(5) . . ? C14 N5 H5 103.3 . . ? C13 N5 H5 103.3 . . ? Cu1 N5 H5 103.3 . . ? C15 N6 C23 117.6(6) . . ? C15 N6 Cu1 110.6(4) . . ? C23 N6 Cu1 131.9(4) . . ? N2 C1 C11 113.2(6) . . ? N2 C1 H1A 108.9 . . ? C11 C1 H1A 108.9 . . ? N2 C1 H1B 108.9 . . ? C11 C1 H1B 108.9 . . ? H1A C1 H1B 107.8 . . ? N2 C2 C3 110.8(6) . . ? N2 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? N3 C3 C2 111.5(6) . . ? N3 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? N3 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? N3 C4 C5 111.4(6) . . ? N3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? N4 C5 C4 112.0(6) . . ? N4 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? N4 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? N4 C6 C7 112.2(7) . . ? N4 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? N4 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? N1 C7 C8 119.7(10) . . ? N1 C7 C6 116.9(7) . . ? C8 C7 C6 123.2(10) . . ? C9 C8 C7 119.8(12) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 120.5(11) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 118.4(12) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? N1 C11 C10 120.4(10) . . ? N1 C11 C1 117.0(7) . . ? C10 C11 C1 122.6(10) . . ? C13 C12 N3 112.3(6) . . ? C13 C12 H12A 109.1 . . ? N3 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? N3 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? N5 C13 C12 115.3(7) . . ? N5 C13 H13A 108.5 . . ? C12 C13 H13A 108.5 . . ? N5 C13 H13B 108.5 . . ? C12 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? N5 C14 C15 112.8(6) . . ? N5 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? N5 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? N6 C15 C16 124.4(7) . . ? N6 C15 C14 117.0(6) . . ? C16 C15 C14 118.6(7) . . ? C17 C16 C15 118.0(7) . . ? C17 C16 H16 121.0 . . ? C15 C16 H16 121.0 . . ? C16 C17 C18 121.6(7) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C17 C18 C23 118.3(8) . . ? C17 C18 C19 124.8(7) . . ? C23 C18 C19 116.9(8) . . ? C20 C19 C18 122.4(7) . . ? C20 C19 H19 118.8 . . ? C18 C19 H19 118.8 . . ? C19 C20 C21 119.3(8) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C20 C21 C22 121.2(8) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C21 C22 C23 120.7(7) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C22 C23 N6 120.4(6) . . ? C22 C23 C18 119.4(7) . . ? N6 C23 C18 120.1(7) . . ? O14 Cl1 O11 121.4(10) . . ? O14 Cl1 O12 110.5(9) . . ? O11 Cl1 O12 109.6(9) . . ? O14 Cl1 O13 104.1(9) . . ? O11 Cl1 O13 104.9(9) . . ? O12 Cl1 O13 104.9(8) . . ? O21 Cl2 O23 110.5(7) . . ? O21 Cl2 O22 111.6(5) . . ? O23 Cl2 O22 108.0(6) . . ? O21 Cl2 O24 105.6(6) . . ? O23 Cl2 O24 111.7(8) . . ? O22 Cl2 O24 109.5(5) . . ? H1D O1 H1C 87.2 . . ? H1D O1 H1C 87.2 . . ? H1C O1 H1D 87.2 . . ? H1C O1 H1D 87.2 . . ? 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 N2 H2 O22 0.91 2.51 3.270(10) 140.9 1_554 N4 H4 O1 0.91 2.56 3.277(10) 136.5 3_666 N5 H5 O22 0.91 2.31 3.160(11) 155.1 1_554 O1 H1C O21 0.84 2.33 3.172(11) 179.1 1_655 O1 H1D O11 0.84 2.34 3.186(18) 178.6 3_666 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.920 _refine_diff_density_min -0.612 _refine_diff_density_rms 0.149