Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Neil Robertson' _publ_contact_author_address ; Department of Chemistry Edinburgh University Joseph Black Building West Mains Road Edinburgh EH9 3JJ UNITED KINGDOM ; _publ_contact_author_email NEIL.ROBERTSON@ED.AC.UK _publ_section_title ; Binuclear and Trinuclear Complexes of exoO2-Cyclam ; loop_ _publ_author_name 'Neil Robertson' 'Russell D. L. Johnstone' 'Nicholas J. Long' 'Keri L. McCall' 'A. Slawin' ; V.A.White ; data_1 _database_code_depnum_ccdc_archive 'CCDC 634705' _audit_creation_date 06-05-17 _audit_creation_method CRYSTALS_ver_12.82 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 17.399(5) _cell_length_b 13.501(4) _cell_length_c 14.678(5) _cell_angle_alpha 90 _cell_angle_beta 90.611(15) _cell_angle_gamma 90 _cell_volume 3448.0(18) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ru -1.2594 0.8363 19.2674 0.8085 12.9182 8.4347 4.8634 24.7997 1.5676 94.2928 5.3787 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C32 H42 Cu1 N10 O10 Ru1 # Dc = 1.72 Fooo = 1828.00 Mu = 11.29 M = 445.68 # Found Formula = C32 H42 Cu1 N10 O10 Ru1 # Dc = 1.72 FOOO = 1828.00 Mu = 11.29 M = 445.68 _chemical_formula_sum 'C32 H42 Cu1 N10 O10 Ru1' _chemical_formula_moiety 'C32 H42 Cu1 N10 O10 Ru1' _chemical_compound_source ? _chemical_formula_weight 891.36 _cell_measurement_reflns_used 3265 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _cell_measurement_temperature 93 _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.717 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1828 _exptl_absorpt_coefficient_mu 1.129 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.41 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type CCD _diffrn_radiation_monochromator CONFOCAL _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method DTPROFIT.REF _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_ambient_temperature 93 _diffrn_reflns_number 11017 _reflns_number_total 3122 _diffrn_reflns_av_R_equivalents 0.138 # Number of reflections with Friedels Law is 3122 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3137 _diffrn_reflns_theta_min 1.909 _diffrn_reflns_theta_max 25.329 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.329 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -20 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -2.14 _refine_diff_density_max 1.69 _refine_ls_number_reflns 2310 _refine_ls_number_restraints 0 _refine_ls_number_parameters 245 #_refine_ls_R_factor_ref 0.0873 _refine_ls_wR_factor_ref 0.0930 _refine_ls_goodness_of_fit_ref 1.0608 #_reflns_number_all 3106 _refine_ls_R_factor_all 0.1089 _refine_ls_wR_factor_all 0.1016 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 2310 _refine_ls_R_factor_gt 0.0873 _refine_ls_wR_factor_gt 0.0930 _refine_ls_shift/su_max 0.000226 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 26.7 24.5 23.7 11.3 ; # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C11 C 0.4739(4) 0.2657(5) 0.2082(5) 0.0336 1.0000 Uani . . . . . . N3 N 0.4555(3) 0.1794(5) 0.1793(4) 0.0382 1.0000 Uani . . . . . . Cu1 Cu 0.5000 0.07456(9) 0.2500 0.0346 1.0000 Uani S T . . . . N4 N 0.4422(6) -0.0316(6) 0.1916(6) 0.0622 1.0000 Uani . . . . . . C15 C 0.4818(9) -0.1235(7) 0.2026(7) 0.0937 1.0000 Uani . . . . . . C14 C 0.4150(5) -0.0137(6) 0.0979(6) 0.0494 1.0000 Uani . . . . . . C13 C 0.3689(6) 0.0764(7) 0.0900(7) 0.0608 1.0000 Uani . . . . . . C12 C 0.4104(5) 0.1697(5) 0.0983(6) 0.0487 1.0000 Uani . . . . . . O1 O 0.4538(3) 0.3481(4) 0.1768(3) 0.0361 1.0000 Uani . . . . . . Ru1 Ru 0.5000 0.46649(6) 0.2500 0.0333 1.0000 Uani S T . . . . N2 N 0.4138(3) 0.4726(4) 0.3394(4) 0.0358 1.0000 Uani . . . . . . C6 C 0.4248(4) 0.5351(5) 0.4108(5) 0.0388 1.0000 Uani . . . . . . C5 C 0.4973(4) 0.5913(5) 0.4054(5) 0.0345 1.0000 Uani . . . . . . N1 N 0.5408(4) 0.5685(4) 0.3337(4) 0.0380 1.0000 Uani . . . . . . C1 C 0.6073(4) 0.6145(5) 0.3274(5) 0.0393 1.0000 Uani . . . . . . C2 C 0.6349(5) 0.6820(6) 0.3890(6) 0.0475 1.0000 Uani . . . . . . C3 C 0.5903(5) 0.7023(6) 0.4617(6) 0.0497 1.0000 Uani . . . . . . C4 C 0.5221(5) 0.6575(5) 0.4716(5) 0.0448 1.0000 Uani . . . . . . C7 C 0.3731(5) 0.5462(6) 0.4784(6) 0.0497 1.0000 Uani . . . . . . C8 C 0.3085(5) 0.4906(6) 0.4747(6) 0.0512 1.0000 Uani . . . . . . C9 C 0.2960(5) 0.4290(7) 0.4035(6) 0.0500 1.0000 Uani . . . . . . C10 C 0.3513(5) 0.4215(6) 0.3392(6) 0.0446 1.0000 Uani . . . . . . O3 O 0.3933(4) 0.0502(6) 0.3750(5) 0.0734 1.0000 Uani . . . . . . N5 N 0.3356(4) 0.0940(6) 0.3540(5) 0.0516 1.0000 Uani . . . . . . O4 O 0.2881(4) 0.0518(6) 0.3048(6) 0.0769 1.0000 Uani . . . . . . O5 O 0.3250(6) 0.1799(8) 0.3732(9) 0.1298 1.0000 Uani . . . . . . O20 O 0.1923(6) 0.3539(9) 0.2289(8) 0.1197 1.0000 Uani . . . . . . C20 C 0.2044(14) 0.2879(12) 0.1520(11) 0.1173 1.0000 Uani . . . . . . H141 H 0.4596 -0.0102 0.0557 0.0591 1.0000 Uiso R . . . . . H142 H 0.3813 -0.0707 0.0804 0.0591 1.0000 Uiso R . . . . . H131 H 0.3285 0.0743 0.1379 0.0731 1.0000 Uiso R . . . . . H132 H 0.3439 0.0752 0.0284 0.0731 1.0000 Uiso R . . . . . H122 H 0.4441 0.1798 0.0443 0.0592 1.0000 Uiso R . . . . . H121 H 0.3708 0.2233 0.1001 0.0592 1.0000 Uiso R . . . . . H11 H 0.6399 0.5987 0.2736 0.0493 1.0000 Uiso R . . . . . H21 H 0.6862 0.7143 0.3823 0.0593 1.0000 Uiso R . . . . . H31 H 0.6072 0.7533 0.5071 0.0585 1.0000 Uiso R . . . . . H41 H 0.4904 0.6707 0.5267 0.0593 1.0000 Uiso R . . . . . H71 H 0.3829 0.5929 0.5301 0.0607 1.0000 Uiso R . . . . . H81 H 0.2694 0.4973 0.5237 0.0606 1.0000 Uiso R . . . . . H91 H 0.2479 0.3886 0.3997 0.0639 1.0000 Uiso R . . . . . H101 H 0.3431 0.3736 0.2880 0.0483 1.0000 Uiso R . . . . . H151 H 0.5171 -0.1386 0.1511 0.1116 1.0000 Uiso R . . . . . H152 H 0.4411 -0.1757 0.2058 0.1116 1.0000 Uiso R . . . . . H1 H 0.1989 0.4189 0.2177 0.1461 1.0000 Uiso R . . . . . H201 H 0.1955 0.2180 0.1716 0.1457 1.0000 Uiso R . . . . . H202 H 0.2585 0.2954 0.1308 0.1457 1.0000 Uiso R . . . . . H203 H 0.1682 0.3048 0.1009 0.1457 1.0000 Uiso R . . . . . H42 H 0.3937 -0.0387 0.2287 0.0763 1.0000 Uiso . . . . . . 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 C11 0.027(3) 0.032(4) 0.041(4) 0.004(3) -0.001(3) -0.006(3) N3 0.038(3) 0.034(3) 0.042(3) 0.007(3) -0.008(3) -0.010(3) Cu1 0.0350(7) 0.0311(7) 0.0377(7) 0.0000 -0.0038(5) 0.0000 N4 0.094(6) 0.044(4) 0.049(4) 0.007(3) -0.017(4) -0.001(4) C15 0.185(14) 0.026(5) 0.068(7) -0.010(4) -0.064(8) -0.004(6) C14 0.059(5) 0.048(5) 0.041(4) -0.002(3) -0.011(3) -0.010(4) C13 0.066(6) 0.053(5) 0.064(6) 0.010(4) -0.017(5) -0.019(4) C12 0.058(5) 0.030(4) 0.058(5) 0.002(3) -0.035(4) -0.011(3) O1 0.039(3) 0.034(3) 0.036(3) 0.002(2) -0.011(2) -0.001(2) Ru1 0.0350(5) 0.0303(5) 0.0345(5) 0.0000 -0.0086(3) 0.0000 N2 0.037(3) 0.034(3) 0.036(3) 0.009(2) -0.014(2) 0.010(2) C6 0.046(4) 0.030(4) 0.040(4) 0.006(3) -0.003(3) 0.010(3) C5 0.046(4) 0.026(3) 0.031(3) 0.006(3) -0.005(3) 0.006(3) N1 0.041(3) 0.027(3) 0.045(4) 0.002(2) -0.013(3) 0.004(2) C1 0.047(4) 0.031(4) 0.040(4) -0.001(3) -0.006(3) -0.001(3) C2 0.045(4) 0.035(4) 0.062(5) 0.004(4) -0.017(4) 0.001(3) C3 0.073(6) 0.026(4) 0.049(4) -0.002(3) -0.022(4) 0.008(4) C4 0.061(5) 0.025(4) 0.048(4) -0.005(3) -0.010(4) 0.013(3) C7 0.056(5) 0.042(5) 0.051(5) 0.003(3) 0.004(4) 0.016(4) C8 0.052(5) 0.045(5) 0.056(5) 0.018(4) 0.012(4) 0.011(4) C9 0.037(4) 0.049(5) 0.064(5) 0.009(4) -0.005(4) 0.008(3) C10 0.040(4) 0.047(5) 0.047(4) 0.006(3) 0.001(3) 0.008(3) O3 0.059(4) 0.099(6) 0.062(4) 0.007(4) -0.014(3) 0.008(4) N5 0.041(4) 0.058(5) 0.057(4) -0.021(3) 0.009(3) -0.006(3) O4 0.050(4) 0.083(5) 0.097(6) -0.033(4) -0.013(4) 0.001(3) O5 0.086(6) 0.093(7) 0.211(12) -0.102(8) -0.022(7) 0.009(5) O20 0.118(8) 0.105(7) 0.137(9) 0.032(7) -0.001(7) -0.026(6) C20 0.183(19) 0.088(11) 0.081(9) -0.002(7) -0.006(10) 0.005(10) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C11 . C11 5_655 1.519(14) yes C11 . N3 . 1.280(10) yes C11 . Cu1 . 2.691(7) yes C11 . O1 . 1.252(9) yes N3 . Cu1 . 1.913(6) yes N3 . C12 . 1.424(9) yes Cu1 . O3 5_655 2.645(8) yes Cu1 . C15 5_655 2.781(9) yes Cu1 . N4 5_655 1.945(8) yes Cu1 . N4 . 1.945(8) yes Cu1 . C15 . 2.781(9) yes Cu1 . O3 . 2.645(8) yes N4 . C15 . 1.427(13) yes N4 . C14 . 1.470(11) yes N4 . H42 . 1.014 no C15 . C15 5_655 1.523(18) yes C15 . H151 . 1.000 no C15 . H152 . 1.000 no C14 . C13 . 1.460(14) yes C14 . H141 . 1.000 no C14 . H142 . 1.000 no C13 . C12 . 1.457(11) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C12 . H122 . 1.000 no C12 . H121 . 1.000 no O1 . Ru1 . 2.082(5) yes Ru1 . N2 5_655 2.006(6) yes Ru1 . N1 5_655 1.973(6) yes Ru1 . N2 . 2.006(6) yes Ru1 . N1 . 1.973(6) yes N2 . C6 . 1.357(10) yes N2 . C10 . 1.288(11) yes C6 . C5 . 1.476(11) yes C6 . C7 . 1.354(11) yes C5 . N1 . 1.338(10) yes C5 . C4 . 1.386(10) yes N1 . C1 . 1.317(10) yes C1 . C2 . 1.368(11) yes C1 . H11 . 1.000 no C2 . C3 . 1.354(13) yes C2 . H21 . 1.000 no C3 . C4 . 1.341(13) yes C3 . H31 . 1.000 no C4 . H41 . 1.000 no C7 . C8 . 1.352(13) yes C7 . H71 . 1.000 no C8 . C9 . 1.352(14) yes C8 . H81 . 1.000 no C9 . C10 . 1.359(12) yes C9 . H91 . 1.000 no C10 . H101 . 1.000 no O3 . N5 . 1.203(10) yes N5 . O4 . 1.232(10) yes N5 . O5 . 1.208(11) yes O20 . C20 . 1.455(18) yes O20 . H1 . 0.900 no C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C11 5_655 C11 . N3 . 114.4(4) yes C11 5_655 C11 . Cu1 . 73.60(15) yes N3 . C11 . Cu1 . 40.8(3) yes C11 5_655 C11 . O1 . 117.3(4) yes N3 . C11 . O1 . 128.3(7) yes Cu1 . C11 . O1 . 169.1(5) yes C11 . N3 . Cu1 . 113.3(5) yes C11 . N3 . C12 . 119.6(6) yes Cu1 . N3 . C12 . 127.0(5) yes O3 5_655 Cu1 . C11 5_655 99.2(2) yes O3 5_655 Cu1 . C11 . 94.5(2) yes C11 5_655 Cu1 . C11 . 32.8(3) yes O3 5_655 Cu1 . C15 5_655 88.6(4) yes C11 5_655 Cu1 . C15 5_655 147.9(3) yes C11 . Cu1 . C15 5_655 176.6(4) yes O3 5_655 Cu1 . N4 5_655 81.4(3) yes C11 5_655 Cu1 . N4 5_655 121.4(3) yes C11 . Cu1 . N4 5_655 153.2(3) yes C15 5_655 Cu1 . N4 5_655 28.8(4) yes O3 5_655 Cu1 . N3 . 89.9(3) yes C11 5_655 Cu1 . N3 . 58.7(2) yes C11 . Cu1 . N3 . 25.9(2) yes C15 5_655 Cu1 . N3 . 153.0(3) yes N4 5_655 Cu1 . N3 . 171.3(3) yes O3 5_655 Cu1 . N3 5_655 100.7(3) yes C11 5_655 Cu1 . N3 5_655 25.9(2) yes C11 . Cu1 . N3 5_655 58.7(2) yes C15 5_655 Cu1 . N3 5_655 122.1(3) yes N4 5_655 Cu1 . N3 5_655 95.8(3) yes O3 5_655 Cu1 . N4 . 88.0(3) yes C11 5_655 Cu1 . N4 . 153.2(3) yes C11 . Cu1 . N4 . 121.4(3) yes C15 5_655 Cu1 . N4 . 57.2(3) yes N4 5_655 Cu1 . N4 . 85.0(5) yes O3 5_655 Cu1 . C15 . 77.6(4) yes C11 5_655 Cu1 . C15 . 176.6(4) yes C11 . Cu1 . C15 . 147.9(3) yes C15 5_655 Cu1 . C15 . 31.8(4) yes N4 5_655 Cu1 . C15 . 57.2(3) yes O3 5_655 Cu1 . O3 . 165.7(4) yes C11 5_655 Cu1 . O3 . 94.5(2) yes C11 . Cu1 . O3 . 99.2(2) yes C15 5_655 Cu1 . O3 . 77.6(4) yes N4 5_655 Cu1 . O3 . 88.0(3) yes N3 . Cu1 . N3 5_655 84.6(4) yes N3 . Cu1 . N4 . 95.8(3) yes N3 5_655 Cu1 . N4 . 171.3(3) yes N3 . Cu1 . C15 . 122.1(3) yes N3 5_655 Cu1 . C15 . 153.0(3) yes N4 . Cu1 . C15 . 28.8(4) yes N3 . Cu1 . O3 . 100.7(3) yes N3 5_655 Cu1 . O3 . 89.9(3) yes N4 . Cu1 . O3 . 81.4(3) yes C15 . Cu1 . O3 . 88.6(4) yes Cu1 . N4 . C15 . 110.1(7) yes Cu1 . N4 . C14 . 116.8(5) yes C15 . N4 . C14 . 113.6(8) yes Cu1 . N4 . H42 . 105.2 no C15 . N4 . H42 . 105.1 no C14 . N4 . H42 . 104.9 no C15 5_655 C15 . N4 . 107.4(8) yes C15 5_655 C15 . Cu1 . 74.11(19) yes N4 . C15 . Cu1 . 41.1(4) yes C15 5_655 C15 . H151 . 116.0 no N4 . C15 . H151 . 113.0 no Cu1 . C15 . H151 . 108.4 no C15 5_655 C15 . H152 . 104.2 no N4 . C15 . H152 . 106.0 no Cu1 . C15 . H152 . 138.1 no H151 . C15 . H152 . 109.5 no N4 . C14 . C13 . 112.5(8) yes N4 . C14 . H141 . 110.1 no C13 . C14 . H141 . 110.0 no N4 . C14 . H142 . 107.1 no C13 . C14 . H142 . 107.6 no H141 . C14 . H142 . 109.5 no C14 . C13 . C12 . 116.3(8) yes C14 . C13 . H131 . 108.1 no C12 . C13 . H131 . 108.5 no C14 . C13 . H132 . 107.0 no C12 . C13 . H132 . 107.5 no H131 . C13 . H132 . 109.5 no C13 . C12 . N3 . 114.6(7) yes C13 . C12 . H122 . 110.2 no N3 . C12 . H122 . 109.1 no C13 . C12 . H121 . 106.7 no N3 . C12 . H121 . 106.6 no H122 . C12 . H121 . 109.5 no C11 . O1 . Ru1 . 112.8(4) yes O1 5_655 Ru1 . O1 . 79.7(3) yes O1 5_655 Ru1 . N2 5_655 94.7(2) yes O1 . Ru1 . N2 5_655 88.9(2) yes O1 5_655 Ru1 . N1 5_655 172.5(2) yes O1 . Ru1 . N1 5_655 94.6(2) yes N2 5_655 Ru1 . N1 5_655 80.2(3) yes O1 5_655 Ru1 . N2 . 88.9(2) yes O1 . Ru1 . N2 . 94.7(2) yes N2 5_655 Ru1 . N2 . 175.3(3) yes N1 5_655 Ru1 . N2 . 96.4(2) yes O1 5_655 Ru1 . N1 . 94.6(2) yes O1 . Ru1 . N1 . 172.5(2) yes N2 5_655 Ru1 . N1 . 96.4(2) yes N1 5_655 Ru1 . N1 . 91.4(3) yes N2 . Ru1 . N1 . 80.2(3) yes Ru1 . N2 . C6 . 115.5(5) yes Ru1 . N2 . C10 . 127.8(6) yes C6 . N2 . C10 . 116.6(7) yes N2 . C6 . C5 . 113.1(6) yes N2 . C6 . C7 . 123.0(8) yes C5 . C6 . C7 . 123.9(7) yes C6 . C5 . N1 . 114.5(6) yes C6 . C5 . C4 . 123.6(7) yes N1 . C5 . C4 . 121.7(7) yes C5 . N1 . Ru1 . 116.6(5) yes C5 . N1 . C1 . 116.8(7) yes Ru1 . N1 . C1 . 126.5(6) yes N1 . C1 . C2 . 124.8(8) yes N1 . C1 . H11 . 117.5 no C2 . C1 . H11 . 117.8 no C1 . C2 . C3 . 117.1(8) yes C1 . C2 . H21 . 122.3 no C3 . C2 . H21 . 120.5 no C2 . C3 . C4 . 120.6(8) yes C2 . C3 . H31 . 119.9 no C4 . C3 . H31 . 119.4 no C5 . C4 . C3 . 118.9(8) yes C5 . C4 . H41 . 120.8 no C3 . C4 . H41 . 120.3 no C6 . C7 . C8 . 117.9(8) yes C6 . C7 . H71 . 121.1 no C8 . C7 . H71 . 121.0 no C7 . C8 . C9 . 120.0(8) yes C7 . C8 . H81 . 119.6 no C9 . C8 . H81 . 120.4 no C8 . C9 . C10 . 118.3(8) yes C8 . C9 . H91 . 120.5 no C10 . C9 . H91 . 121.2 no C9 . C10 . N2 . 124.2(8) yes C9 . C10 . H101 . 118.3 no N2 . C10 . H101 . 117.5 no Cu1 . O3 . N5 . 110.5(6) yes O3 . N5 . O4 . 118.4(8) yes O3 . N5 . O5 . 122.8(9) yes O4 . N5 . O5 . 118.5(9) yes C20 . O20 . H1 . 115.8 no O20 . C20 . H201 . 109.3 no O20 . C20 . H202 . 108.9 no H201 . C20 . H202 . 109.5 no O20 . C20 . H203 . 110.2 no H201 . C20 . H203 . 109.5 no H202 . C20 . H203 . 109.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O20 . H1 . O4 7_555 179.7 0.900 1.840 2.740(15) yes N4 . H42 . O20 7_545 142.6 1.014 2.179 3.047(15) yes