# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email joresfu1@upvnet.upv.es _publ_contact_author_name 'Jorge Escorihuela' loop_ _publ_author_name S.Luis 'Ines Marti' 'Armando Ferrer' 'Jorge Escorihuela' I.M.Burguete data_str1148m _database_code_depnum_ccdc_archive 'CCDC 801764' #TrackingRef 'str1148m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 Cu N4 O2' _chemical_formula_sum 'C18 H20 Cu N4 O2' _chemical_formula_weight 387.92 _chemical_absolute_configuration ad 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.4048(11) _cell_length_b 11.3542(13) _cell_length_c 14.9983(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1771.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used 2738 _cell_measurement_theta_min 5.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7176 _exptl_absorpt_correction_T_max 0.8070 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _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 CCD three-circle diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 14747 _diffrn_reflns_av_R_equivalents 0.0833 _diffrn_reflns_av_sigmaI/netI 0.0760 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3612 _reflns_number_gt 2321 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2005)' _computing_cell_refinement 'SMART (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.0503P)^2^+1.2297P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(3) _refine_ls_number_reflns 3612 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1022 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1244 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.47234(7) 0.33818(5) 0.60749(4) 0.0465(2) Uani 1 1 d . . . O1 O 0.4680(5) 0.6106(3) 0.7753(2) 0.0626(11) Uani 1 1 d . . . O2 O 0.6971(4) 0.3282(4) 0.3933(3) 0.0798(14) Uani 1 1 d . . . N1 N 0.5089(5) 0.4871(3) 0.6587(3) 0.0515(13) Uani 1 1 d . . . N2 N 0.3607(5) 0.3153(4) 0.7136(3) 0.0455(12) Uani 1 1 d . . . H2A H 0.2820 0.2920 0.6961 0.055 Uiso 1 1 calc R . . H2B H 0.3941 0.2589 0.7488 0.055 Uiso 1 1 calc R . . N3 N 0.5824(5) 0.3875(4) 0.5157(3) 0.0575(14) Uani 1 1 d . . . N4 N 0.4723(5) 0.1846(3) 0.5435(3) 0.0541(12) Uani 1 1 d . . . H4A H 0.5043 0.1283 0.5794 0.065 Uiso 1 1 calc R . . H4B H 0.3912 0.1648 0.5292 0.065 Uiso 1 1 calc R . . C1 C 0.4520(6) 0.5171(4) 0.7322(3) 0.0394(13) Uani 1 1 d . . . C2 C 0.3507(6) 0.4285(5) 0.7646(4) 0.0430(14) Uani 1 1 d . . . H2 H 0.2660 0.4623 0.7520 0.052 Uiso 1 1 calc R . . C3 C 0.6167(6) 0.3132(5) 0.4531(4) 0.0491(15) Uani 1 1 d . . . C4 C 0.5516(6) 0.1922(4) 0.4606(3) 0.0478(15) Uani 1 1 d . . . H4 H 0.6189 0.1320 0.4639 0.057 Uiso 1 1 calc R . . C5 C 0.6077(6) 0.5558(5) 0.6149(4) 0.0565(16) Uani 1 1 d . . . H5A H 0.6856 0.5544 0.6505 0.068 Uiso 1 1 calc R . . H5B H 0.5797 0.6370 0.6099 0.068 Uiso 1 1 calc R . . C6 C 0.6362(8) 0.5065(5) 0.5216(5) 0.077(2) Uani 1 1 d . . . H6A H 0.5978 0.5566 0.4765 0.092 Uiso 1 1 calc R . . H6B H 0.7282 0.5041 0.5116 0.092 Uiso 1 1 calc R . . C11 C 0.3574(6) 0.4047(4) 0.8648(3) 0.0423(14) Uani 1 1 d . . . C12 C 0.2456(8) 0.4017(7) 0.9136(5) 0.082(2) Uani 1 1 d . . . H12 H 0.1673 0.4182 0.8866 0.098 Uiso 1 1 calc R . . C13 C 0.2508(12) 0.3738(9) 1.0031(7) 0.119(4) Uani 1 1 d . . . H13 H 0.1756 0.3733 1.0366 0.143 Uiso 1 1 calc R . . C14 C 0.3632(14) 0.3475(8) 1.0423(5) 0.113(4) Uani 1 1 d . . . H14 H 0.3643 0.3259 1.1021 0.135 Uiso 1 1 calc R . . C15 C 0.4761(10) 0.3518(5) 0.9957(4) 0.084(2) Uani 1 1 d . . . H15 H 0.5540 0.3351 1.0233 0.101 Uiso 1 1 calc R . . C16 C 0.4709(7) 0.3821(4) 0.9056(4) 0.0565(15) Uani 1 1 d . . . H16 H 0.5467 0.3868 0.8729 0.068 Uiso 1 1 calc R . . C21 C 0.4703(5) 0.1682(4) 0.3777(3) 0.0441(11) Uani 1 1 d . . . C22 C 0.3676(6) 0.2371(6) 0.3571(4) 0.0623(18) Uani 1 1 d . . . H22 H 0.3476 0.3016 0.3927 0.075 Uiso 1 1 calc R . . C23 C 0.2927(7) 0.2114(8) 0.2829(6) 0.083(2) Uani 1 1 d . . . H23 H 0.2224 0.2584 0.2686 0.100 Uiso 1 1 calc R . . C24 C 0.3237(9) 0.1151(9) 0.2304(5) 0.090(3) Uani 1 1 d . . . H24 H 0.2750 0.0988 0.1799 0.108 Uiso 1 1 calc R . . C25 C 0.4224(8) 0.0452(7) 0.2513(5) 0.075(2) Uani 1 1 d . . . H25 H 0.4404 -0.0206 0.2166 0.090 Uiso 1 1 calc R . . C26 C 0.4980(6) 0.0713(5) 0.3249(4) 0.0554(17) Uani 1 1 d . . . H26 H 0.5676 0.0234 0.3389 0.066 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 Cu1 0.0738(4) 0.0301(3) 0.0357(3) -0.0031(3) 0.0035(4) -0.0054(3) O1 0.101(3) 0.0379(19) 0.049(2) -0.0107(16) -0.002(3) -0.005(2) O2 0.089(3) 0.061(3) 0.089(3) -0.014(3) 0.043(3) -0.007(3) N1 0.080(4) 0.032(2) 0.042(2) -0.0023(19) 0.009(3) -0.002(3) N2 0.068(3) 0.035(3) 0.033(2) -0.0039(19) -0.009(2) -0.011(2) N3 0.084(4) 0.036(2) 0.053(3) -0.005(2) 0.010(3) -0.011(2) N4 0.089(3) 0.034(2) 0.038(2) -0.0011(18) -0.003(3) -0.007(3) C1 0.054(4) 0.028(2) 0.037(3) 0.000(2) -0.008(3) 0.007(3) C2 0.045(3) 0.035(3) 0.049(4) -0.007(3) -0.006(3) 0.003(3) C3 0.057(4) 0.046(4) 0.045(3) -0.002(3) 0.006(3) 0.004(3) C4 0.066(4) 0.034(3) 0.043(3) -0.002(2) 0.006(3) 0.006(3) C5 0.086(4) 0.039(3) 0.044(4) 0.003(3) -0.003(4) -0.010(3) C6 0.110(6) 0.042(4) 0.078(5) -0.010(3) 0.032(5) -0.007(4) C11 0.058(4) 0.039(3) 0.030(3) -0.008(2) 0.004(3) -0.008(3) C12 0.077(5) 0.106(6) 0.061(5) -0.032(4) 0.017(4) -0.026(4) C13 0.154(10) 0.132(10) 0.069(7) -0.029(6) 0.054(7) -0.070(8) C14 0.236(13) 0.064(5) 0.038(4) -0.002(4) 0.021(7) -0.062(8) C15 0.154(7) 0.049(4) 0.048(4) 0.001(3) -0.029(5) -0.008(5) C16 0.080(4) 0.048(3) 0.041(3) 0.000(2) -0.001(4) 0.009(3) C21 0.057(3) 0.042(2) 0.033(3) 0.005(2) 0.006(3) 0.005(3) C22 0.070(4) 0.063(4) 0.054(4) 0.005(3) -0.002(3) 0.023(4) C23 0.059(5) 0.119(7) 0.072(5) 0.042(5) -0.003(4) 0.013(5) C24 0.085(6) 0.138(8) 0.046(4) -0.006(5) -0.004(4) -0.028(6) C25 0.084(6) 0.083(5) 0.057(5) -0.010(4) -0.005(4) -0.006(4) C26 0.069(5) 0.053(3) 0.044(3) -0.003(3) 0.003(3) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.877(5) . ? Cu1 N1 1.895(4) . ? Cu1 N2 1.987(4) . ? Cu1 N4 1.990(4) . ? O1 C1 1.254(6) . ? O2 C3 1.239(7) . ? N1 C1 1.297(6) . ? N1 C5 1.448(7) . ? N2 C2 1.500(6) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? N3 C3 1.311(7) . ? N3 C6 1.465(8) . ? N4 C4 1.494(7) . ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? C1 C2 1.536(8) . ? C2 C11 1.528(7) . ? C2 H2 0.9800 . ? C3 C4 1.536(7) . ? C4 C21 1.528(7) . ? C4 H4 0.9800 . ? C5 C6 1.536(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C11 C16 1.355(8) . ? C11 C12 1.375(9) . ? C12 C13 1.380(12) . ? C12 H12 0.9300 . ? C13 C14 1.342(14) . ? C13 H13 0.9300 . ? C14 C15 1.367(13) . ? C14 H14 0.9300 . ? C15 C16 1.397(8) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 C22 1.359(8) . ? C21 C26 1.386(7) . ? C22 C23 1.390(10) . ? C22 H22 0.9300 . ? C23 C24 1.385(11) . ? C23 H23 0.9300 . ? C24 C25 1.335(11) . ? C24 H24 0.9300 . ? C25 C26 1.387(9) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N1 84.8(2) . . ? N3 Cu1 N2 169.55(18) . . ? N1 Cu1 N2 84.82(18) . . ? N3 Cu1 N4 84.68(19) . . ? N1 Cu1 N4 167.6(2) . . ? N2 Cu1 N4 105.76(18) . . ? C1 N1 C5 124.6(5) . . ? C1 N1 Cu1 119.1(4) . . ? C5 N1 Cu1 116.1(3) . . ? C2 N2 Cu1 109.7(3) . . ? C2 N2 H2A 109.7 . . ? Cu1 N2 H2A 109.7 . . ? C2 N2 H2B 109.7 . . ? Cu1 N2 H2B 109.7 . . ? H2A N2 H2B 108.2 . . ? C3 N3 C6 122.2(5) . . ? C3 N3 Cu1 120.0(4) . . ? C6 N3 Cu1 117.6(4) . . ? C4 N4 Cu1 110.6(3) . . ? C4 N4 H4A 109.5 . . ? Cu1 N4 H4A 109.5 . . ? C4 N4 H4B 109.5 . . ? Cu1 N4 H4B 109.5 . . ? H4A N4 H4B 108.1 . . ? O1 C1 N1 126.9(5) . . ? O1 C1 C2 118.8(5) . . ? N1 C1 C2 114.2(4) . . ? N2 C2 C11 110.3(4) . . ? N2 C2 C1 110.6(4) . . ? C11 C2 C1 113.3(5) . . ? N2 C2 H2 107.4 . . ? C11 C2 H2 107.4 . . ? C1 C2 H2 107.4 . . ? O2 C3 N3 127.9(6) . . ? O2 C3 C4 118.3(5) . . ? N3 C3 C4 113.8(5) . . ? N4 C4 C21 111.2(5) . . ? N4 C4 C3 110.8(4) . . ? C21 C4 C3 110.1(4) . . ? N4 C4 H4 108.2 . . ? C21 C4 H4 108.2 . . ? C3 C4 H4 108.2 . . ? N1 C5 C6 110.7(5) . . ? N1 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N3 C6 C5 108.6(5) . . ? N3 C6 H6A 110.0 . . ? C5 C6 H6A 110.0 . . ? N3 C6 H6B 110.0 . . ? C5 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? C16 C11 C12 119.5(6) . . ? C16 C11 C2 121.1(5) . . ? C12 C11 C2 119.4(6) . . ? C11 C12 C13 119.4(9) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 120.7(9) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 121.1(8) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C14 C15 C16 118.0(8) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? C11 C16 C15 121.2(7) . . ? C11 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C22 C21 C26 119.3(5) . . ? C22 C21 C4 121.2(5) . . ? C26 C21 C4 119.4(5) . . ? C21 C22 C23 120.2(7) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C24 C23 C22 119.3(7) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C25 C24 C23 121.0(8) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C24 C25 C26 119.7(8) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C21 C26 C25 120.4(6) . . ? C21 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 N1 C1 177.0(5) . . . . ? N2 Cu1 N1 C1 -2.2(4) . . . . ? N4 Cu1 N1 C1 -151.4(7) . . . . ? N3 Cu1 N1 C5 -7.6(4) . . . . ? N2 Cu1 N1 C5 173.2(4) . . . . ? N4 Cu1 N1 C5 24.1(11) . . . . ? N3 Cu1 N2 C2 4.3(14) . . . . ? N1 Cu1 N2 C2 8.7(4) . . . . ? N4 Cu1 N2 C2 -177.9(3) . . . . ? N1 Cu1 N3 C3 172.1(5) . . . . ? N2 Cu1 N3 C3 176.5(10) . . . . ? N4 Cu1 N3 C3 -1.4(5) . . . . ? N1 Cu1 N3 C6 -2.5(5) . . . . ? N2 Cu1 N3 C6 1.8(15) . . . . ? N4 Cu1 N3 C6 -176.0(5) . . . . ? N3 Cu1 N4 C4 -1.7(4) . . . . ? N1 Cu1 N4 C4 -33.3(11) . . . . ? N2 Cu1 N4 C4 178.7(3) . . . . ? C5 N1 C1 O1 3.1(9) . . . . ? Cu1 N1 C1 O1 178.2(5) . . . . ? C5 N1 C1 C2 -180.0(5) . . . . ? Cu1 N1 C1 C2 -4.9(6) . . . . ? Cu1 N2 C2 C11 -139.1(4) . . . . ? Cu1 N2 C2 C1 -12.9(5) . . . . ? O1 C1 C2 N2 -170.9(5) . . . . ? N1 C1 C2 N2 11.9(6) . . . . ? O1 C1 C2 C11 -46.4(7) . . . . ? N1 C1 C2 C11 136.4(5) . . . . ? C6 N3 C3 O2 1.6(11) . . . . ? Cu1 N3 C3 O2 -172.7(5) . . . . ? C6 N3 C3 C4 178.4(6) . . . . ? Cu1 N3 C3 C4 4.0(7) . . . . ? Cu1 N4 C4 C21 -118.9(4) . . . . ? Cu1 N4 C4 C3 3.9(6) . . . . ? O2 C3 C4 N4 171.9(5) . . . . ? N3 C3 C4 N4 -5.1(7) . . . . ? O2 C3 C4 C21 -64.6(7) . . . . ? N3 C3 C4 C21 118.3(6) . . . . ? C1 N1 C5 C6 -169.7(6) . . . . ? Cu1 N1 C5 C6 15.2(7) . . . . ? C3 N3 C6 C5 -163.5(6) . . . . ? Cu1 N3 C6 C5 10.9(8) . . . . ? N1 C5 C6 N3 -15.9(8) . . . . ? N2 C2 C11 C16 77.6(6) . . . . ? C1 C2 C11 C16 -47.1(7) . . . . ? N2 C2 C11 C12 -99.8(6) . . . . ? C1 C2 C11 C12 135.6(6) . . . . ? C16 C11 C12 C13 -1.0(10) . . . . ? C2 C11 C12 C13 176.4(7) . . . . ? C11 C12 C13 C14 -1.3(14) . . . . ? C12 C13 C14 C15 2.5(15) . . . . ? C13 C14 C15 C16 -1.3(12) . . . . ? C12 C11 C16 C15 2.2(8) . . . . ? C2 C11 C16 C15 -175.2(5) . . . . ? C14 C15 C16 C11 -1.0(9) . . . . ? N4 C4 C21 C22 60.1(6) . . . . ? C3 C4 C21 C22 -63.1(7) . . . . ? N4 C4 C21 C26 -116.9(5) . . . . ? C3 C4 C21 C26 119.9(5) . . . . ? C26 C21 C22 C23 -1.0(9) . . . . ? C4 C21 C22 C23 -178.0(6) . . . . ? C21 C22 C23 C24 0.0(10) . . . . ? C22 C23 C24 C25 1.6(11) . . . . ? C23 C24 C25 C26 -2.1(12) . . . . ? C22 C21 C26 C25 0.5(9) . . . . ? C4 C21 C26 C25 177.5(5) . . . . ? C24 C25 C26 C21 1.1(10) . . . . ? 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 H2A O2 0.90 2.11 2.850(6) 139.2 4_456 N2 H2B O1 0.90 2.24 2.934(6) 133.4 3_646 N4 H4A O1 0.90 2.21 2.911(5) 134.7 3_646 N4 H4B O2 0.90 2.33 3.020(7) 133.3 4_456 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.313 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.070 data_str1184m _database_code_depnum_ccdc_archive 'CCDC 829491' #TrackingRef '5810_web_deposit_cif_file_0_JorgeEscorihuela_1307960811.str1184m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H26 Cu N4 O2, 2(C H4 O)' _chemical_formula_sum 'C23 H34 Cu N4 O4' _chemical_formula_weight 494.08 _chemical_absolute_configuration ad 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.5315(2) _cell_length_b 12.0135(3) _cell_length_c 20.7584(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2376.98(9) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6523 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 30.5 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044 _exptl_absorpt_coefficient_mu 0.955 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6662 _exptl_absorpt_correction_T_max 0.8174 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 CCD three-circle diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 19297 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 30.53 _reflns_number_total 7096 _reflns_number_gt 6507 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SMART (Bruker, 1995)' _computing_data_reduction 'SAINT (Bruker, 1995)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.0362P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(4) _refine_ls_number_reflns 7096 _refine_ls_number_parameters 315 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0667 _refine_ls_wR_factor_gt 0.0648 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 6.248 _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 0.20020(10) 0.78991(8) 0.62594(5) 0.0202(3) Uani 1 1 d . . . O1 O 0.0210(9) 0.9835(6) 0.7598(4) 0.0360(17) Uani 1 1 d . . . O2 O 0.5840(6) 0.7994(6) 0.5497(3) 0.0299(14) Uani 1 1 d . . . N1 N 0.0430(8) 0.7212(6) 0.6764(3) 0.0220(14) Uani 1 1 d D . . H1A H -0.036(8) 0.722(10) 0.654(4) 0.03(3) Uiso 1 1 d D . . H1B H 0.058(12) 0.651(5) 0.687(5) 0.03(3) Uiso 1 1 d D . . N2 N 0.1404(8) 0.9244(6) 0.6698(4) 0.0244(15) Uani 1 1 d . . . N3 N 0.3670(8) 0.8513(6) 0.5883(4) 0.0244(15) Uani 1 1 d . . . N4 N 0.2507(8) 0.6571(7) 0.5713(4) 0.0231(14) Uani 1 1 d D . . H4A H 0.199(12) 0.663(9) 0.539(5) 0.02(3) Uiso 1 1 d . . . H4B H 0.232(14) 0.595(7) 0.591(5) 0.04(3) Uiso 1 1 d D . . C1 C 0.1224(10) 0.7450(8) 0.7891(5) 0.0281(19) Uani 1 1 d . . . H1C H 0.1048 0.7879 0.8279 0.034 Uiso 1 1 calc R . . H1D H 0.0978 0.6683 0.7982 0.034 Uiso 1 1 calc R . . C2 C 0.0259(9) 0.7883(8) 0.7354(4) 0.0228(15) Uani 1 1 d . . . H2 H -0.0718 0.7834 0.7499 0.027 Uiso 1 1 calc R . . C3 C 0.0608(10) 0.9094(7) 0.7208(4) 0.0240(17) Uani 1 1 d . . . C4 C 0.1951(13) 1.0363(8) 0.6589(5) 0.035(2) Uani 1 1 d . . . H4C H 0.2503 1.0587 0.6959 0.042 Uiso 1 1 calc R . . H4D H 0.1171 1.0878 0.6550 0.042 Uiso 1 1 calc R . . C5 C 0.2853(11) 1.0439(7) 0.5989(5) 0.032(2) Uani 1 1 d . . . H5A H 0.3184 1.1199 0.5946 0.038 Uiso 1 1 calc R . . H5B H 0.2270 1.0279 0.5617 0.038 Uiso 1 1 calc R . . C6 C 0.4114(10) 0.9667(8) 0.5974(5) 0.0297(19) Uani 1 1 d . . . H6A H 0.4735 0.9883 0.5625 0.036 Uiso 1 1 calc R . . H6B H 0.4629 0.9732 0.6375 0.036 Uiso 1 1 calc R . . C7 C 0.4576(9) 0.7792(8) 0.5654(4) 0.0233(16) Uani 1 1 d . . . C8 C 0.4023(9) 0.6606(8) 0.5577(4) 0.0229(16) Uani 1 1 d . . . H8 H 0.4493 0.6142 0.5900 0.027 Uiso 1 1 calc R . . C9 C 0.4412(10) 0.6146(8) 0.4910(4) 0.0272(18) Uani 1 1 d . . . H9A H 0.3963 0.6602 0.4584 0.033 Uiso 1 1 calc R . . H9B H 0.5418 0.6215 0.4853 0.033 Uiso 1 1 calc R . . C11 C 0.2776(10) 0.7505(8) 0.7740(4) 0.0267(18) Uani 1 1 d . . . C12 C 0.3543(13) 0.8438(10) 0.7897(7) 0.047(3) Uani 1 1 d . . . H12 H 0.3101 0.9042 0.8090 0.056 Uiso 1 1 calc R . . C13 C 0.4990(15) 0.8486(13) 0.7767(10) 0.069(5) Uani 1 1 d . . . H13 H 0.5502 0.9115 0.7881 0.083 Uiso 1 1 calc R . . C14 C 0.5642(13) 0.7615(13) 0.7474(8) 0.059(4) Uani 1 1 d . . . H14 H 0.6595 0.7654 0.7380 0.071 Uiso 1 1 calc R . . C15 C 0.4893(14) 0.6680(12) 0.7318(6) 0.049(3) Uani 1 1 d . . . H15 H 0.5340 0.6084 0.7118 0.059 Uiso 1 1 calc R . . C16 C 0.3468(12) 0.6616(10) 0.7456(5) 0.037(2) Uani 1 1 d . . . H16 H 0.2974 0.5971 0.7356 0.044 Uiso 1 1 calc R . . C21 C 0.4001(10) 0.4947(8) 0.4801(4) 0.0252(17) Uani 1 1 d . . . C22 C 0.2872(11) 0.4692(9) 0.4400(4) 0.032(2) Uani 1 1 d . . . H22 H 0.2378 0.5262 0.4199 0.038 Uiso 1 1 calc R . . C23 C 0.2481(13) 0.3591(10) 0.4299(5) 0.038(2) Uani 1 1 d . . . H23 H 0.1723 0.3428 0.4033 0.046 Uiso 1 1 calc R . . C24 C 0.3210(12) 0.2744(9) 0.4590(5) 0.041(3) Uani 1 1 d . . . H24 H 0.2939 0.2009 0.4524 0.049 Uiso 1 1 calc RD . . C25 C 0.4338(12) 0.2981(10) 0.4977(6) 0.039(2) Uani 1 1 d . . . H25 H 0.4846 0.2405 0.5164 0.047 Uiso 1 1 calc R . . C26 C 0.4721(11) 0.4077(9) 0.5089(5) 0.033(2) Uani 1 1 d . . . H26 H 0.5471 0.4230 0.5361 0.039 Uiso 1 1 calc R . . O31 O -0.1729(10) 0.9623(7) 0.8502(4) 0.047(2) Uani 1 1 d D . . H31 H -0.119(12) 0.967(13) 0.820(5) 0.05(4) Uiso 1 1 d D . . C31 C -0.1631(19) 0.8682(12) 0.8880(7) 0.068(5) Uani 1 1 d . . . H31A H -0.0663 0.8536 0.8976 0.103 Uiso 1 1 calc R . . H31B H -0.2021 0.8059 0.8652 0.103 Uiso 1 1 calc R . . H31C H -0.2139 0.8795 0.9274 0.103 Uiso 1 1 calc R . . O41 O 0.7788(9) 0.6790(8) 0.6141(5) 0.052(2) Uani 1 1 d D . . H41 H 0.722(11) 0.712(10) 0.592(5) 0.04(4) Uiso 1 1 d D . . C41 C 0.8100(17) 0.5774(11) 0.5843(7) 0.057(3) Uani 1 1 d . . . H41A H 0.8444 0.5909 0.5415 0.086 Uiso 1 1 calc R . . H41B H 0.7267 0.5326 0.5821 0.086 Uiso 1 1 calc R . . H41C H 0.8804 0.5390 0.6088 0.086 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 Cu1 0.0195(4) 0.0183(4) 0.0227(5) -0.0013(4) 0.0019(4) -0.0005(4) O1 0.046(5) 0.026(4) 0.035(4) -0.006(3) 0.015(3) 0.000(3) O2 0.021(3) 0.028(3) 0.041(4) 0.001(3) 0.006(3) -0.001(3) N1 0.021(3) 0.018(3) 0.027(3) -0.001(3) 0.000(3) -0.001(3) N2 0.027(4) 0.019(3) 0.027(4) 0.001(3) 0.006(3) 0.000(3) N3 0.023(4) 0.019(3) 0.032(4) -0.001(3) 0.005(3) -0.003(3) N4 0.022(3) 0.021(4) 0.027(4) -0.001(3) 0.004(3) -0.001(3) C1 0.029(5) 0.031(5) 0.024(4) 0.005(4) 0.002(3) -0.001(4) C2 0.021(4) 0.022(4) 0.025(4) 0.000(4) 0.004(3) -0.002(4) C3 0.025(4) 0.021(4) 0.026(4) 0.000(3) 0.002(3) 0.001(3) C4 0.042(5) 0.018(4) 0.045(5) -0.001(4) 0.016(5) 0.000(4) C5 0.036(5) 0.019(4) 0.040(5) 0.006(3) 0.010(4) 0.001(4) C6 0.026(4) 0.022(4) 0.041(5) 0.000(4) 0.004(4) -0.004(4) C7 0.022(4) 0.023(4) 0.025(4) 0.002(3) -0.001(3) 0.001(3) C8 0.021(4) 0.023(4) 0.025(4) 0.003(3) 0.002(3) 0.002(3) C9 0.028(4) 0.027(4) 0.027(4) -0.001(3) 0.008(3) 0.001(4) C11 0.027(5) 0.029(4) 0.024(4) 0.004(3) -0.003(3) 0.000(3) C12 0.033(5) 0.034(6) 0.073(8) -0.009(6) -0.008(6) 0.000(5) C13 0.036(7) 0.046(8) 0.125(15) 0.004(8) -0.014(8) -0.012(6) C14 0.024(5) 0.067(10) 0.086(10) 0.017(8) -0.002(6) 0.005(6) C15 0.037(6) 0.059(8) 0.050(7) -0.004(6) -0.005(5) 0.019(6) C16 0.034(5) 0.035(5) 0.041(5) -0.004(5) -0.010(4) 0.005(4) C21 0.024(4) 0.026(4) 0.025(4) -0.002(3) 0.008(3) 0.002(3) C22 0.033(5) 0.036(5) 0.027(4) -0.005(4) 0.001(4) 0.005(4) C23 0.039(5) 0.042(6) 0.033(5) -0.014(4) 0.003(4) -0.004(5) C24 0.048(6) 0.031(5) 0.044(5) -0.011(4) 0.018(5) -0.004(5) C25 0.039(5) 0.028(5) 0.050(6) 0.005(5) 0.010(5) 0.005(5) C26 0.026(4) 0.031(5) 0.041(5) 0.002(4) 0.002(4) 0.001(4) O31 0.064(6) 0.032(4) 0.045(4) 0.004(3) 0.028(4) 0.012(4) C31 0.096(12) 0.047(7) 0.062(8) 0.022(6) 0.049(8) 0.031(8) O41 0.035(4) 0.058(6) 0.062(5) -0.007(4) -0.019(4) 0.008(4) C41 0.064(9) 0.045(7) 0.061(8) 0.000(6) -0.025(7) -0.002(7) _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 N3 1.919(7) . ? Cu1 N2 1.940(8) . ? Cu1 N1 2.006(7) . ? Cu1 N4 2.016(8) . ? O1 C3 1.262(11) . ? O2 C7 1.272(10) . ? N1 C2 1.476(11) . ? N1 H1A 0.88(6) . ? N1 H1B 0.88(6) . ? N2 C3 1.315(12) . ? N2 C4 1.459(12) . ? N3 C7 1.312(11) . ? N3 C6 1.461(12) . ? N4 C8 1.474(12) . ? N4 H4A 0.83(11) . ? N4 H4B 0.87(6) . ? C1 C11 1.513(13) . ? C1 C2 1.536(13) . ? C1 H1C 0.9700 . ? C1 H1D 0.9700 . ? C2 C3 1.523(13) . ? C2 H2 0.9800 . ? C4 C5 1.517(13) . ? C4 H4C 0.9700 . ? C4 H4D 0.9700 . ? C5 C6 1.519(14) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.527(13) . ? C8 C9 1.535(12) . ? C8 H8 0.9800 . ? C9 C21 1.509(13) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.378(15) . ? C11 C16 1.386(15) . ? C12 C13 1.41(2) . ? C12 H12 0.9300 . ? C13 C14 1.36(2) . ? C13 H13 0.9300 . ? C14 C15 1.37(2) . ? C14 H14 0.9300 . ? C15 C16 1.390(18) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 C26 1.386(14) . ? C21 C22 1.395(14) . ? C22 C23 1.390(16) . ? C22 H22 0.9300 . ? C23 C24 1.372(17) . ? C23 H23 0.9300 . ? C24 C25 1.372(17) . ? C24 H24 0.9300 . ? C25 C26 1.386(16) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? O31 C31 1.379(15) . ? O31 H31 0.81(6) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? O41 C41 1.401(16) . ? O41 H41 0.81(6) . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N2 96.6(3) . . ? N3 Cu1 N1 171.8(3) . . ? N2 Cu1 N1 83.0(3) . . ? N3 Cu1 N4 83.0(3) . . ? N2 Cu1 N4 173.3(3) . . ? N1 Cu1 N4 98.4(3) . . ? C2 N1 Cu1 106.9(5) . . ? C2 N1 H1A 109(7) . . ? Cu1 N1 H1A 111(7) . . ? C2 N1 H1B 110(7) . . ? Cu1 N1 H1B 114(7) . . ? H1A N1 H1B 106(10) . . ? C3 N2 C4 117.2(8) . . ? C3 N2 Cu1 115.7(6) . . ? C4 N2 Cu1 126.1(6) . . ? C7 N3 C6 118.9(8) . . ? C7 N3 Cu1 116.0(6) . . ? C6 N3 Cu1 123.5(6) . . ? C8 N4 Cu1 108.6(6) . . ? C8 N4 H4A 115(7) . . ? Cu1 N4 H4A 104(8) . . ? C8 N4 H4B 109(9) . . ? Cu1 N4 H4B 111(8) . . ? H4A N4 H4B 109(10) . . ? C11 C1 C2 114.9(7) . . ? C11 C1 H1C 108.5 . . ? C2 C1 H1C 108.5 . . ? C11 C1 H1D 108.5 . . ? C2 C1 H1D 108.5 . . ? H1C C1 H1D 107.5 . . ? N1 C2 C3 109.4(7) . . ? N1 C2 C1 110.6(8) . . ? C3 C2 C1 109.7(8) . . ? N1 C2 H2 109.1 . . ? C3 C2 H2 109.1 . . ? C1 C2 H2 109.1 . . ? O1 C3 N2 126.5(9) . . ? O1 C3 C2 118.7(8) . . ? N2 C3 C2 114.7(8) . . ? N2 C4 C5 112.7(7) . . ? N2 C4 H4C 109.1 . . ? C5 C4 H4C 109.1 . . ? N2 C4 H4D 109.1 . . ? C5 C4 H4D 109.1 . . ? H4C C4 H4D 107.8 . . ? C4 C5 C6 115.4(8) . . ? C4 C5 H5A 108.4 . . ? C6 C5 H5A 108.4 . . ? C4 C5 H5B 108.4 . . ? C6 C5 H5B 108.4 . . ? H5A C5 H5B 107.5 . . ? N3 C6 C5 110.7(8) . . ? N3 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? O2 C7 N3 126.2(9) . . ? O2 C7 C8 118.5(8) . . ? N3 C7 C8 115.3(7) . . ? N4 C8 C7 110.2(7) . . ? N4 C8 C9 113.5(8) . . ? C7 C8 C9 110.3(7) . . ? N4 C8 H8 107.5 . . ? C7 C8 H8 107.5 . . ? C9 C8 H8 107.5 . . ? C21 C9 C8 114.6(7) . . ? C21 C9 H9A 108.6 . . ? C8 C9 H9A 108.6 . . ? C21 C9 H9B 108.6 . . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C12 C11 C16 118.3(10) . . ? C12 C11 C1 120.3(10) . . ? C16 C11 C1 121.3(9) . . ? C11 C12 C13 120.6(12) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 120.1(13) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 119.9(12) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 120.3(12) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C11 C16 C15 120.7(11) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C26 C21 C22 118.2(9) . . ? C26 C21 C9 121.8(9) . . ? C22 C21 C9 120.0(9) . . ? C23 C22 C21 120.5(10) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C24 C23 C22 120.2(10) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C23 120.1(10) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.1(11) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C21 C26 C25 120.9(10) . . ? C21 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? C31 O31 H31 117(10) . . ? O31 C31 H31A 109.5 . . ? O31 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O31 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C41 O41 H41 109(10) . . ? O41 C41 H41A 109.5 . . ? O41 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? O41 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? 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 N2 Cu1 N1 C2 -27.6(6) . . . . ? N4 Cu1 N1 C2 159.0(6) . . . . ? N3 Cu1 N2 C3 -154.6(7) . . . . ? N1 Cu1 N2 C3 17.1(7) . . . . ? N3 Cu1 N2 C4 13.4(9) . . . . ? N1 Cu1 N2 C4 -174.8(9) . . . . ? N2 Cu1 N3 C7 165.2(7) . . . . ? N4 Cu1 N3 C7 -21.5(7) . . . . ? N2 Cu1 N3 C6 -0.1(8) . . . . ? N4 Cu1 N3 C6 173.2(8) . . . . ? N3 Cu1 N4 C8 23.4(6) . . . . ? N1 Cu1 N4 C8 -148.4(6) . . . . ? Cu1 N1 C2 C3 33.0(8) . . . . ? Cu1 N1 C2 C1 -87.9(7) . . . . ? C11 C1 C2 N1 61.6(11) . . . . ? C11 C1 C2 C3 -59.1(11) . . . . ? C4 N2 C3 O1 3.8(15) . . . . ? Cu1 N2 C3 O1 172.9(8) . . . . ? C4 N2 C3 C2 -170.9(8) . . . . ? Cu1 N2 C3 C2 -1.7(10) . . . . ? N1 C2 C3 O1 163.2(8) . . . . ? C1 C2 C3 O1 -75.4(11) . . . . ? N1 C2 C3 N2 -21.7(11) . . . . ? C1 C2 C3 N2 99.7(9) . . . . ? C3 N2 C4 C5 180.0(9) . . . . ? Cu1 N2 C4 C5 12.1(13) . . . . ? N2 C4 C5 C6 -58.0(12) . . . . ? C7 N3 C6 C5 158.2(8) . . . . ? Cu1 N3 C6 C5 -36.9(11) . . . . ? C4 C5 C6 N3 71.6(11) . . . . ? C6 N3 C7 O2 -0.1(14) . . . . ? Cu1 N3 C7 O2 -166.0(7) . . . . ? C6 N3 C7 C8 179.8(8) . . . . ? Cu1 N3 C7 C8 13.9(10) . . . . ? Cu1 N4 C8 C7 -21.9(8) . . . . ? Cu1 N4 C8 C9 -146.2(6) . . . . ? O2 C7 C8 N4 -173.6(8) . . . . ? N3 C7 C8 N4 6.5(11) . . . . ? O2 C7 C8 C9 -47.4(10) . . . . ? N3 C7 C8 C9 132.6(8) . . . . ? N4 C8 C9 C21 -59.8(11) . . . . ? C7 C8 C9 C21 176.0(8) . . . . ? C2 C1 C11 C12 90.0(12) . . . . ? C2 C1 C11 C16 -91.3(11) . . . . ? C16 C11 C12 C13 0.3(19) . . . . ? C1 C11 C12 C13 179.0(13) . . . . ? C11 C12 C13 C14 1(2) . . . . ? C12 C13 C14 C15 -1(3) . . . . ? C13 C14 C15 C16 0(2) . . . . ? C12 C11 C16 C15 -1.6(16) . . . . ? C1 C11 C16 C15 179.7(10) . . . . ? C14 C15 C16 C11 1.4(19) . . . . ? C8 C9 C21 C26 -73.7(11) . . . . ? C8 C9 C21 C22 106.5(10) . . . . ? C26 C21 C22 C23 0.5(14) . . . . ? C9 C21 C22 C23 -179.7(9) . . . . ? C21 C22 C23 C24 -0.4(15) . . . . ? C22 C23 C24 C25 -0.7(15) . . . . ? C23 C24 C25 C26 1.8(16) . . . . ? C22 C21 C26 C25 0.6(15) . . . . ? C9 C21 C26 C25 -179.2(9) . . . . ? C24 C25 C26 C21 -1.7(17) . . . . ? 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 N1 H1A O41 0.88(6) 2.02(6) 2.875(11) 163(11) 1_455 N1 H1B O1 0.88(6) 2.42(8) 3.206(10) 149(10) 3_546 N4 H4A O2 0.83(11) 2.19(11) 3.017(11) 171(11) 4_466 N4 H4B O31 0.87(6) 2.09(6) 2.946(11) 171(12) 3_546 O31 H31 O1 0.81(6) 1.84(6) 2.646(11) 172(15) . O41 H41 O2 0.81(6) 1.90(6) 2.707(11) 173(13) . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.443 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.045