# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Olof Einarsdottir' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of California Santa Cruz 95064 UNITED STATES OF AMERICA ; _publ_contact_author_email OLOF@CHEMISTRY.UCSC.EDU _publ_section_title ; Synthesis and structural characterization of cross-linked histidine-phenol Cu(II) complexes as cytochrome c oxidase active site models ; loop_ _publ_author_name 'Olof Einarsdottir' 'Istvan Szundi' 'Joseph Konopelski' 'Yakira R. Landaverry' ; M.Olmstead ; 'Indranil Sen' 'Kimberly White' data_lb01 _database_code_depnum_ccdc_archive 'CCDC 640795' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 5' _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 Cl Cu N4 O3, Cl O4' _chemical_formula_sum 'C20 H22 Cl2 Cu N4 O7' _chemical_formula_weight 564.86 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.54460(10) _cell_length_b 25.6151(5) _cell_length_c 26.3379(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4415.30(15) _cell_formula_units_Z 8 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 9637 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 31.5 _exptl_crystal_description needle _exptl_crystal_colour blue-green _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.699 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2312 _exptl_absorpt_coefficient_mu 1.284 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5424 _exptl_absorpt_correction_T_max 0.9043 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(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 Apex II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean '8.3 pixels/mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 58910 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.48 _reflns_number_total 10144 _reflns_number_gt 9744 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex 2 (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL-97 _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^)+(0.0373P)^2^+2.3681P] 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' _chemical_absolute_configuration ad _refine_ls_abs_structure_Flack -0.002(5) _refine_ls_number_reflns 10144 _refine_ls_number_parameters 623 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0640 _refine_ls_wR_factor_gt 0.0628 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.003 _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 0.21306(3) 0.212926(9) 0.474525(8) 0.01017(5) Uani 1 1 d . . . Cl1 Cl 0.27641(7) 0.283742(17) 0.524650(16) 0.01394(9) Uani 1 1 d . . . O9 O 0.1312(3) 0.06603(6) 0.34645(6) 0.0230(3) Uani 1 1 d . . . O10 O -0.1910(2) 0.09351(6) 0.35908(6) 0.0195(3) Uani 1 1 d . . . O11 O 0.1212(2) 0.40727(6) 0.42929(5) 0.0149(3) Uani 1 1 d D . . H11 H 0.096(4) 0.4327(8) 0.4460(9) 0.018 Uiso 1 1 d D . . N1 N 0.2046(2) 0.16440(6) 0.53403(6) 0.0115(3) Uani 1 1 d . . . N2 N 0.1924(2) 0.14377(6) 0.43406(6) 0.0105(3) Uani 1 1 d . . . N3 N 0.2309(3) 0.25494(6) 0.41183(6) 0.0118(3) Uani 1 1 d . . . N4 N 0.2154(3) 0.32503(6) 0.36362(6) 0.0117(3) Uani 1 1 d . . . C1 C 0.2430(3) 0.17644(8) 0.58303(7) 0.0133(4) Uani 1 1 d . . . H1A H 0.2860 0.2108 0.5912 0.016 Uiso 1 1 calc R . . C2 C 0.2214(3) 0.14029(8) 0.62156(8) 0.0150(4) Uani 1 1 d . . . H2A H 0.2473 0.1499 0.6558 0.018 Uiso 1 1 calc R . . C3 C 0.1616(3) 0.08971(8) 0.60972(8) 0.0150(4) Uani 1 1 d . . . H3A H 0.1465 0.0642 0.6357 0.018 Uiso 1 1 calc R . . C4 C 0.1244(3) 0.07707(8) 0.55976(8) 0.0137(4) Uani 1 1 d . . . H4A H 0.0857 0.0426 0.5507 0.016 Uiso 1 1 calc R . . C5 C 0.1442(3) 0.11558(7) 0.52273(7) 0.0123(4) Uani 1 1 d . . . C6 C 0.0869(3) 0.10615(7) 0.46823(8) 0.0129(4) Uani 1 1 d . . . H6A H 0.1248 0.0701 0.4586 0.015 Uiso 1 1 calc R . . H6B H -0.0628 0.1098 0.4642 0.015 Uiso 1 1 calc R . . C7 C 0.4066(3) 0.12534(8) 0.42555(8) 0.0151(4) Uani 1 1 d . . . H7A H 0.4041 0.0917 0.4079 0.023 Uiso 1 1 calc R . . H7B H 0.4756 0.1213 0.4583 0.023 Uiso 1 1 calc R . . H7C H 0.4803 0.1510 0.4049 0.023 Uiso 1 1 calc R . . C8 C 0.1756(3) 0.18328(8) 0.34632(7) 0.0140(4) Uani 1 1 d . . . H8A H 0.3135 0.1689 0.3398 0.017 Uiso 1 1 calc R . . H8B H 0.0972 0.1813 0.3142 0.017 Uiso 1 1 calc R . . C9 C 0.0692(3) 0.14998(7) 0.38649(8) 0.0110(4) Uani 1 1 d . . . H9A H -0.0606 0.1681 0.3959 0.013 Uiso 1 1 calc R . . C10 C 0.0112(3) 0.09794(7) 0.36231(7) 0.0131(4) Uani 1 1 d . . . C11 C -0.2694(4) 0.04813(9) 0.33299(9) 0.0229(5) Uani 1 1 d . . . H11A H -0.4181 0.0511 0.3297 0.034 Uiso 1 1 calc R . . H11B H -0.2358 0.0167 0.3524 0.034 Uiso 1 1 calc R . . H11C H -0.2076 0.0459 0.2992 0.034 Uiso 1 1 calc R . . C12 C 0.1949(3) 0.23926(8) 0.36198(7) 0.0131(4) Uani 1 1 d . . . C13 C 0.1826(3) 0.28228(8) 0.33216(7) 0.0147(4) Uani 1 1 d . . . H13A H 0.1567 0.2831 0.2967 0.018 Uiso 1 1 calc R . . C14 C 0.2433(3) 0.30642(8) 0.41102(8) 0.0127(4) Uani 1 1 d . . . H14A H 0.2686 0.3275 0.4400 0.015 Uiso 1 1 calc R . . C15 C 0.1764(3) 0.41928(8) 0.38094(8) 0.0143(4) Uani 1 1 d . . . C16 C 0.1955(3) 0.47057(8) 0.36398(8) 0.0184(4) Uani 1 1 d . . . H16A H 0.1614 0.4985 0.3861 0.022 Uiso 1 1 calc R . . C17 C 0.2635(3) 0.48128(8) 0.31534(8) 0.0199(4) Uani 1 1 d . . . H17A H 0.2760 0.5165 0.3044 0.024 Uiso 1 1 calc R . . C18 C 0.3135(3) 0.44104(8) 0.28254(8) 0.0184(4) Uani 1 1 d . . . H18A H 0.3594 0.4484 0.2491 0.022 Uiso 1 1 calc R . . C19 C 0.2959(3) 0.38951(8) 0.29912(8) 0.0161(4) Uani 1 1 d . . . H19A H 0.3321 0.3617 0.2770 0.019 Uiso 1 1 calc R . . C20 C 0.2261(3) 0.37852(7) 0.34753(8) 0.0125(4) Uani 1 1 d . . . Cl3 Cl 0.31525(8) 0.70718(2) 0.23655(2) 0.02053(11) Uani 1 1 d . . . O1 O 0.3859(4) 0.65487(8) 0.24279(8) 0.0442(5) Uani 1 1 d . . . O2 O 0.4509(3) 0.74232(7) 0.26367(7) 0.0310(4) Uani 1 1 d . . . O3 O 0.3091(3) 0.72055(8) 0.18392(6) 0.0341(4) Uani 1 1 d . . . O4 O 0.1144(3) 0.71272(9) 0.25888(7) 0.0373(5) Uani 1 1 d . . . Cl4 Cl 0.13170(8) 0.518003(18) 0.513547(19) 0.01630(10) Uani 1 1 d . . . O5 O -0.0231(2) 0.48867(6) 0.48540(6) 0.0221(3) Uani 1 1 d . . . O6 O 0.3264(2) 0.49289(6) 0.50616(7) 0.0285(4) Uani 1 1 d . . . O7 O 0.1371(3) 0.57053(6) 0.49490(6) 0.0243(3) Uani 1 1 d . . . O8 O 0.0774(3) 0.51740(7) 0.56630(6) 0.0286(4) Uani 1 1 d . . . Cu2 Cu 0.14189(4) 0.776745(8) 0.533130(8) 0.01016(5) Uani 1 1 d . . . Cl2 Cl 0.05891(7) 0.718229(17) 0.470626(17) 0.01207(9) Uani 1 1 d . . . O19 O 0.1211(3) 0.94018(7) 0.65143(6) 0.0298(4) Uani 1 1 d . . . O20 O 0.4080(3) 0.89556(6) 0.66664(6) 0.0207(3) Uani 1 1 d . . . O21 O 0.2629(2) 0.80009(5) 0.34067(5) 0.0154(3) Uani 1 1 d D . . H21 H 0.304(4) 0.7855(9) 0.3162(7) 0.018 Uiso 1 1 d D . . N11 N 0.1652(2) 0.72091(6) 0.58516(6) 0.0110(3) Uani 1 1 d . . . N12 N 0.1450(3) 0.82529(6) 0.59751(6) 0.0111(3) Uani 1 1 d . . . N13 N 0.1256(3) 0.83540(6) 0.48568(6) 0.0112(3) Uani 1 1 d . . . N14 N 0.1714(3) 0.87781(6) 0.41374(6) 0.0109(3) Uani 1 1 d . . . C21 C 0.1405(3) 0.66890(7) 0.57827(7) 0.0129(4) Uani 1 1 d . . . H21A H 0.0954 0.6565 0.5462 0.015 Uiso 1 1 calc R . . C22 C 0.1789(3) 0.63329(8) 0.61651(8) 0.0139(4) Uani 1 1 d . . . H22A H 0.1594 0.5970 0.6108 0.017 Uiso 1 1 calc R . . C23 C 0.2461(3) 0.65103(8) 0.66325(8) 0.0144(4) Uani 1 1 d . . . H23A H 0.2747 0.6271 0.6899 0.017 Uiso 1 1 calc R . . C24 C 0.2708(3) 0.70413(8) 0.67068(7) 0.0138(4) Uani 1 1 d . . . H24A H 0.3154 0.7172 0.7026 0.017 Uiso 1 1 calc R . . C25 C 0.2295(3) 0.73805(7) 0.63076(7) 0.0108(4) Uani 1 1 d . . . C26 C 0.2658(3) 0.79556(7) 0.63576(7) 0.0124(4) Uani 1 1 d . . . H26A H 0.2267 0.8071 0.6703 0.015 Uiso 1 1 calc R . . H26B H 0.4130 0.8030 0.6310 0.015 Uiso 1 1 calc R . . C27 C -0.0711(3) 0.82905(8) 0.61524(8) 0.0156(4) Uani 1 1 d . . . H27A H -0.0770 0.8502 0.6462 0.023 Uiso 1 1 calc R . . H27B H -0.1237 0.7940 0.6224 0.023 Uiso 1 1 calc R . . H27C H -0.1546 0.8454 0.5888 0.023 Uiso 1 1 calc R . . C28 C 0.1286(3) 0.91025(7) 0.54866(7) 0.0139(4) Uani 1 1 d . . . H28A H -0.0172 0.9127 0.5584 0.017 Uiso 1 1 calc R . . H28B H 0.1852 0.9461 0.5484 0.017 Uiso 1 1 calc R . . C29 C 0.2417(3) 0.87815(7) 0.58869(7) 0.0122(4) Uani 1 1 d . . . H29A H 0.3854 0.8727 0.5769 0.015 Uiso 1 1 calc R . . C30 C 0.2471(3) 0.90909(8) 0.63865(8) 0.0165(4) Uani 1 1 d . . . C31 C 0.4093(4) 0.91504(10) 0.71835(9) 0.0276(6) Uani 1 1 d . . . H31A H 0.5261 0.9003 0.7367 0.041 Uiso 1 1 calc R . . H31B H 0.2823 0.9048 0.7354 0.041 Uiso 1 1 calc R . . H31C H 0.4203 0.9532 0.7179 0.041 Uiso 1 1 calc R . . C32 C 0.1424(3) 0.88824(7) 0.49633(7) 0.0119(4) Uani 1 1 d . . . C33 C 0.1430(3) 0.83073(7) 0.43570(7) 0.0122(4) Uani 1 1 d . . . H33A H 0.1363 0.7986 0.4178 0.015 Uiso 1 1 calc R . . C34 C 0.1699(3) 0.91447(7) 0.45243(7) 0.0127(4) Uani 1 1 d . . . H34A H 0.1854 0.9512 0.4487 0.015 Uiso 1 1 calc R . . C35 C 0.2286(3) 0.84974(8) 0.32495(8) 0.0131(4) Uani 1 1 d . . . C36 C 0.2310(3) 0.86288(8) 0.27326(8) 0.0157(4) Uani 1 1 d . . . H36A H 0.2565 0.8365 0.2487 0.019 Uiso 1 1 calc R . . C37 C 0.1967(3) 0.91355(9) 0.25751(8) 0.0187(4) Uani 1 1 d . . . H37A H 0.1965 0.9217 0.2223 0.022 Uiso 1 1 calc R . . C38 C 0.1627(4) 0.95248(8) 0.29303(8) 0.0204(4) Uani 1 1 d . . . H38A H 0.1441 0.9876 0.2824 0.024 Uiso 1 1 calc R . . C39 C 0.1561(4) 0.93988(8) 0.34429(8) 0.0172(4) Uani 1 1 d . . . H39A H 0.1294 0.9665 0.3685 0.021 Uiso 1 1 calc R . . C40 C 0.1879(3) 0.88905(8) 0.36064(7) 0.0124(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01215(11) 0.00965(10) 0.00869(10) -0.00106(8) -0.00047(8) -0.00036(8) Cl1 0.0184(2) 0.0127(2) 0.0108(2) -0.00235(17) -0.00098(17) -0.00201(17) O9 0.0207(8) 0.0180(7) 0.0302(9) -0.0105(6) -0.0022(7) 0.0027(7) O10 0.0155(8) 0.0200(8) 0.0230(7) -0.0087(6) 0.0001(6) -0.0045(6) O11 0.0175(7) 0.0122(7) 0.0148(7) -0.0028(5) 0.0016(6) 0.0008(6) N1 0.0100(7) 0.0119(7) 0.0126(8) -0.0015(6) -0.0009(6) 0.0011(6) N2 0.0095(8) 0.0106(7) 0.0113(8) -0.0010(6) 0.0001(6) -0.0003(6) N3 0.0108(8) 0.0129(8) 0.0118(8) -0.0021(6) -0.0012(6) 0.0000(6) N4 0.0114(8) 0.0123(8) 0.0113(7) -0.0005(6) -0.0010(6) -0.0011(6) C1 0.0103(9) 0.0159(9) 0.0137(9) -0.0013(7) -0.0003(7) 0.0008(7) C2 0.0136(9) 0.0207(10) 0.0107(9) -0.0019(8) 0.0002(8) 0.0011(8) C3 0.0108(9) 0.0183(10) 0.0160(9) 0.0042(8) 0.0023(8) 0.0024(8) C4 0.0097(9) 0.0134(9) 0.0179(10) 0.0011(7) 0.0001(8) 0.0005(8) C5 0.0075(8) 0.0155(9) 0.0140(9) 0.0000(7) 0.0007(8) 0.0014(7) C6 0.0149(9) 0.0112(9) 0.0127(9) -0.0007(7) -0.0002(7) -0.0021(7) C7 0.0120(10) 0.0176(10) 0.0158(10) -0.0023(8) 0.0007(7) 0.0019(8) C8 0.0180(10) 0.0129(9) 0.0111(9) -0.0008(7) 0.0015(8) 0.0002(8) C9 0.0117(8) 0.0112(9) 0.0102(9) -0.0027(7) -0.0010(7) 0.0009(7) C10 0.0181(10) 0.0117(9) 0.0095(8) 0.0000(7) -0.0004(8) -0.0020(8) C11 0.0218(11) 0.0233(11) 0.0236(11) -0.0090(9) 0.0009(9) -0.0101(9) C12 0.0117(9) 0.0146(9) 0.0130(9) -0.0011(7) 0.0007(7) -0.0004(7) C13 0.0186(10) 0.0140(9) 0.0114(8) -0.0031(7) -0.0003(7) -0.0005(8) C14 0.0121(9) 0.0144(9) 0.0118(9) -0.0001(7) 0.0007(7) -0.0005(7) C15 0.0104(9) 0.0155(9) 0.0169(9) 0.0000(7) -0.0011(8) -0.0010(7) C16 0.0173(10) 0.0141(10) 0.0238(11) -0.0029(8) -0.0035(9) -0.0012(8) C17 0.0194(11) 0.0146(9) 0.0255(11) 0.0067(8) -0.0065(9) -0.0034(8) C18 0.0193(11) 0.0211(10) 0.0149(10) 0.0058(8) -0.0030(8) -0.0049(8) C19 0.0155(10) 0.0179(10) 0.0150(9) 0.0009(8) -0.0013(8) -0.0018(8) C20 0.0104(9) 0.0116(9) 0.0157(9) 0.0025(7) -0.0030(8) -0.0009(7) Cl3 0.0217(3) 0.0233(2) 0.0166(2) -0.00677(19) -0.00212(19) 0.0009(2) O1 0.0627(15) 0.0243(10) 0.0457(12) -0.0076(8) 0.0053(11) 0.0092(10) O2 0.0291(9) 0.0344(10) 0.0294(9) -0.0082(8) -0.0094(8) -0.0061(8) O3 0.0287(9) 0.0552(12) 0.0183(8) -0.0007(8) -0.0021(7) -0.0065(9) O4 0.0270(9) 0.0601(13) 0.0249(9) -0.0074(9) 0.0054(7) 0.0038(10) Cl4 0.0159(2) 0.0135(2) 0.0195(2) -0.00512(18) -0.0011(2) 0.00212(19) O5 0.0178(7) 0.0208(8) 0.0279(8) -0.0101(6) -0.0043(7) -0.0004(6) O6 0.0165(8) 0.0234(8) 0.0457(11) -0.0107(8) -0.0052(8) 0.0085(7) O7 0.0233(8) 0.0158(7) 0.0337(9) 0.0013(6) 0.0059(8) 0.0000(7) O8 0.0421(11) 0.0266(9) 0.0170(8) -0.0033(7) -0.0022(7) 0.0042(8) Cu2 0.01300(11) 0.00917(10) 0.00831(10) -0.00050(8) -0.00047(9) -0.00041(9) Cl2 0.0147(2) 0.0113(2) 0.01026(19) -0.00158(18) -0.00117(16) -0.00059(16) O19 0.0328(10) 0.0319(9) 0.0248(9) -0.0150(7) -0.0043(8) 0.0109(8) O20 0.0284(9) 0.0179(8) 0.0156(8) -0.0060(6) -0.0079(6) -0.0001(6) O21 0.0236(8) 0.0121(7) 0.0105(6) -0.0009(5) 0.0015(6) 0.0035(6) N11 0.0108(7) 0.0122(8) 0.0098(7) -0.0005(6) 0.0018(6) -0.0009(6) N12 0.0117(8) 0.0108(7) 0.0108(7) 0.0004(6) 0.0001(7) -0.0003(7) N13 0.0116(8) 0.0108(7) 0.0111(7) 0.0005(6) -0.0005(7) 0.0002(6) N14 0.0103(8) 0.0116(7) 0.0109(7) 0.0010(6) -0.0002(6) -0.0001(6) C21 0.0114(9) 0.0146(9) 0.0126(9) -0.0016(7) 0.0014(8) -0.0013(8) C22 0.0136(10) 0.0124(9) 0.0157(9) 0.0012(7) 0.0022(8) 0.0000(7) C23 0.0129(9) 0.0159(9) 0.0145(9) 0.0035(7) 0.0026(8) 0.0011(8) C24 0.0139(9) 0.0174(9) 0.0101(9) -0.0011(7) 0.0003(7) 0.0012(8) C25 0.0092(9) 0.0133(9) 0.0101(9) -0.0009(7) 0.0017(7) -0.0007(7) C26 0.0145(9) 0.0128(9) 0.0100(8) -0.0015(7) -0.0034(7) -0.0001(8) C27 0.0123(9) 0.0191(10) 0.0154(10) -0.0034(8) 0.0016(7) 0.0004(7) C28 0.0187(10) 0.0112(9) 0.0116(9) -0.0011(7) -0.0009(8) 0.0015(8) C29 0.0143(9) 0.0103(9) 0.0119(9) -0.0018(7) 0.0002(7) -0.0011(7) C30 0.0207(11) 0.0145(9) 0.0144(9) -0.0031(8) 0.0009(8) -0.0021(8) C31 0.0443(16) 0.0261(12) 0.0125(10) -0.0060(9) -0.0064(10) -0.0050(11) C32 0.0120(8) 0.0120(9) 0.0116(9) -0.0008(7) -0.0021(8) 0.0009(8) C33 0.0132(9) 0.0117(9) 0.0117(8) -0.0004(7) -0.0013(8) -0.0001(8) C34 0.0153(10) 0.0104(8) 0.0125(9) -0.0001(7) -0.0017(7) 0.0006(7) C35 0.0118(9) 0.0132(9) 0.0142(9) 0.0016(7) -0.0014(8) -0.0001(7) C36 0.0156(9) 0.0190(10) 0.0123(9) -0.0016(8) 0.0019(8) 0.0007(8) C37 0.0218(11) 0.0237(11) 0.0105(9) 0.0051(8) 0.0014(8) 0.0007(9) C38 0.0304(12) 0.0134(9) 0.0173(10) 0.0048(8) -0.0003(9) 0.0022(9) C39 0.0228(11) 0.0139(9) 0.0148(9) -0.0002(7) 0.0005(9) 0.0019(9) C40 0.0121(9) 0.0150(9) 0.0103(8) 0.0019(7) -0.0010(7) -0.0007(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 1.9745(17) . ? Cu1 N1 2.0010(16) . ? Cu1 N2 2.0716(16) . ? Cu1 Cl1 2.2815(5) . ? Cu1 Cl1 2.8591(5) 4_456 ? Cl1 Cu1 2.8591(5) 4_556 ? O9 C10 1.208(3) . ? O10 C10 1.331(3) . ? O10 C11 1.444(2) . ? O11 C15 1.359(2) . ? O11 H11 0.805(16) . ? N1 C5 1.345(2) . ? N1 C1 1.350(2) . ? N2 C6 1.488(2) . ? N2 C7 1.496(2) . ? N2 C9 1.499(2) . ? N3 C14 1.321(3) . ? N3 C12 1.393(2) . ? N4 C14 1.349(3) . ? N4 C13 1.390(2) . ? N4 C20 1.436(2) . ? C1 C2 1.381(3) . ? C1 H1A 0.9500 . ? C2 C3 1.389(3) . ? C2 H2A 0.9500 . ? C3 C4 1.377(3) . ? C3 H3A 0.9500 . ? C4 C5 1.393(3) . ? C4 H4A 0.9500 . ? C5 C6 1.503(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C12 1.497(3) . ? C8 C9 1.527(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.525(3) . ? C9 H9A 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.356(3) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C16 1.393(3) . ? C15 C20 1.404(3) . ? C16 C17 1.384(3) . ? C16 H16A 0.9500 . ? C17 C18 1.384(3) . ? C17 H17A 0.9500 . ? C18 C19 1.395(3) . ? C18 H18A 0.9500 . ? C19 C20 1.383(3) . ? C19 H19A 0.9500 . ? Cl3 O1 1.427(2) . ? Cl3 O3 1.4283(17) . ? Cl3 O4 1.4473(19) . ? Cl3 O2 1.4518(17) . ? Cl4 O7 1.4327(16) . ? Cl4 O8 1.4343(17) . ? Cl4 O6 1.4406(16) . ? Cl4 O5 1.4631(16) . ? Cu2 N13 1.9573(16) . ? Cu2 N11 1.9867(16) . ? Cu2 N12 2.1029(16) . ? Cu2 Cl2 2.2916(5) . ? Cu2 Cl2 2.7340(5) 4_566 ? Cl2 Cu2 2.7340(5) 4_466 ? O19 C30 1.195(3) . ? O20 C30 1.332(3) . ? O20 C31 1.450(3) . ? O21 C35 1.356(2) . ? O21 H21 0.791(16) . ? N11 C25 1.346(2) . ? N11 C21 1.354(2) . ? N12 C26 1.490(2) . ? N12 C27 1.493(3) . ? N12 C29 1.512(2) . ? N13 C33 1.326(2) . ? N13 C32 1.387(2) . ? N14 C33 1.350(2) . ? N14 C34 1.386(2) . ? N14 C40 1.432(2) . ? C21 C22 1.382(3) . ? C21 H21A 0.9500 . ? C22 C23 1.384(3) . ? C22 H22A 0.9500 . ? C23 C24 1.384(3) . ? C23 H23A 0.9500 . ? C24 C25 1.391(3) . ? C24 H24A 0.9500 . ? C25 C26 1.498(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C32 1.492(3) . ? C28 C29 1.528(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.536(3) . ? C29 H29A 1.0000 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 C34 1.349(3) . ? C33 H33A 0.9500 . ? C34 H34A 0.9500 . ? C35 C36 1.402(3) . ? C35 C40 1.403(3) . ? C36 C37 1.381(3) . ? C36 H36A 0.9500 . ? C37 C38 1.385(3) . ? C37 H37A 0.9500 . ? C38 C39 1.389(3) . ? C38 H38A 0.9500 . ? C39 C40 1.387(3) . ? C39 H39A 0.9500 . ? 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 174.38(7) . . ? N3 Cu1 N2 92.27(7) . . ? N1 Cu1 N2 82.53(6) . . ? N3 Cu1 Cl1 92.28(5) . . ? N1 Cu1 Cl1 92.62(5) . . ? N2 Cu1 Cl1 171.63(5) . . ? N3 Cu1 Cl1 92.83(5) . 4_456 ? N1 Cu1 Cl1 89.14(5) . 4_456 ? N2 Cu1 Cl1 87.96(5) . 4_456 ? Cl1 Cu1 Cl1 98.829(15) . 4_456 ? Cu1 Cl1 Cu1 102.108(17) . 4_556 ? C10 O10 C11 116.88(17) . . ? C15 O11 H11 112.7(19) . . ? C5 N1 C1 118.58(17) . . ? C5 N1 Cu1 114.35(13) . . ? C1 N1 Cu1 126.98(13) . . ? C6 N2 C7 108.72(15) . . ? C6 N2 C9 108.93(15) . . ? C7 N2 C9 114.36(15) . . ? C6 N2 Cu1 105.84(11) . . ? C7 N2 Cu1 106.62(12) . . ? C9 N2 Cu1 111.99(12) . . ? C14 N3 C12 106.44(17) . . ? C14 N3 Cu1 124.13(14) . . ? C12 N3 Cu1 128.39(13) . . ? C14 N4 C13 107.11(16) . . ? C14 N4 C20 127.14(17) . . ? C13 N4 C20 125.70(16) . . ? N1 C1 C2 122.02(19) . . ? N1 C1 H1A 119.0 . . ? C2 C1 H1A 119.0 . . ? C1 C2 C3 119.30(19) . . ? C1 C2 H2A 120.4 . . ? C3 C2 H2A 120.4 . . ? C4 C3 C2 118.93(19) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 119.08(19) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? N1 C5 C4 122.06(18) . . ? N1 C5 C6 115.73(16) . . ? C4 C5 C6 122.10(17) . . ? N2 C6 C5 110.95(15) . . ? N2 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.0 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C12 C8 C9 112.49(16) . . ? C12 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? C12 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? N2 C9 C10 112.96(16) . . ? N2 C9 C8 113.15(16) . . ? C10 C9 C8 108.20(16) . . ? N2 C9 H9A 107.4 . . ? C10 C9 H9A 107.4 . . ? C8 C9 H9A 107.4 . . ? O9 C10 O10 124.51(19) . . ? O9 C10 C9 125.1(2) . . ? O10 C10 C9 110.38(17) . . ? O10 C11 H11A 109.5 . . ? O10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 N3 108.76(17) . . ? C13 C12 C8 127.86(18) . . ? N3 C12 C8 123.38(17) . . ? C12 C13 N4 106.62(16) . . ? C12 C13 H13A 126.7 . . ? N4 C13 H13A 126.7 . . ? N3 C14 N4 111.06(18) . . ? N3 C14 H14A 124.5 . . ? N4 C14 H14A 124.5 . . ? O11 C15 C16 122.53(18) . . ? O11 C15 C20 118.72(17) . . ? C16 C15 C20 118.67(19) . . ? C17 C16 C15 120.8(2) . . ? C17 C16 H16A 119.6 . . ? C15 C16 H16A 119.6 . . ? C18 C17 C16 120.42(19) . . ? C18 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? C17 C18 C19 119.31(19) . . ? C17 C18 H18A 120.3 . . ? C19 C18 H18A 120.3 . . ? C20 C19 C18 120.6(2) . . ? C20 C19 H19A 119.7 . . ? C18 C19 H19A 119.7 . . ? C19 C20 C15 120.19(18) . . ? C19 C20 N4 118.83(18) . . ? C15 C20 N4 120.91(18) . . ? O1 Cl3 O3 110.23(12) . . ? O1 Cl3 O4 109.86(14) . . ? O3 Cl3 O4 110.20(11) . . ? O1 Cl3 O2 109.10(13) . . ? O3 Cl3 O2 110.24(12) . . ? O4 Cl3 O2 107.14(11) . . ? O7 Cl4 O8 110.38(10) . . ? O7 Cl4 O6 110.57(11) . . ? O8 Cl4 O6 110.21(11) . . ? O7 Cl4 O5 109.00(10) . . ? O8 Cl4 O5 108.27(11) . . ? O6 Cl4 O5 108.35(9) . . ? N13 Cu2 N11 175.79(7) . . ? N13 Cu2 N12 93.52(6) . . ? N11 Cu2 N12 82.46(6) . . ? N13 Cu2 Cl2 91.75(5) . . ? N11 Cu2 Cl2 92.46(5) . . ? N12 Cu2 Cl2 165.54(5) . . ? N13 Cu2 Cl2 89.73(5) . 4_566 ? N11 Cu2 Cl2 88.98(5) . 4_566 ? N12 Cu2 Cl2 89.52(5) . 4_566 ? Cl2 Cu2 Cl2 103.968(15) . 4_566 ? Cu2 Cl2 Cu2 103.401(17) . 4_466 ? C30 O20 C31 115.77(18) . . ? C35 O21 H21 104.6(18) . . ? C25 N11 C21 118.54(16) . . ? C25 N11 Cu2 113.87(12) . . ? C21 N11 Cu2 127.34(13) . . ? C26 N12 C27 108.91(15) . . ? C26 N12 C29 109.83(15) . . ? C27 N12 C29 112.77(16) . . ? C26 N12 Cu2 104.36(11) . . ? C27 N12 Cu2 106.33(12) . . ? C29 N12 Cu2 114.18(11) . . ? C33 N13 C32 106.39(16) . . ? C33 N13 Cu2 124.03(13) . . ? C32 N13 Cu2 128.00(13) . . ? C33 N14 C34 106.82(16) . . ? C33 N14 C40 127.47(16) . . ? C34 N14 C40 125.62(16) . . ? N11 C21 C22 122.00(18) . . ? N11 C21 H21A 119.0 . . ? C22 C21 H21A 119.0 . . ? C21 C22 C23 119.30(18) . . ? C21 C22 H22A 120.3 . . ? C23 C22 H22A 120.3 . . ? C22 C23 C24 119.06(18) . . ? C22 C23 H23A 120.5 . . ? C24 C23 H23A 120.5 . . ? C23 C24 C25 118.98(18) . . ? C23 C24 H24A 120.5 . . ? C25 C24 H24A 120.5 . . ? N11 C25 C24 122.11(17) . . ? N11 C25 C26 116.66(16) . . ? C24 C25 C26 121.15(17) . . ? N11 C25 Cu2 40.20(9) . . ? C24 C25 Cu2 161.87(14) . . ? C26 C25 Cu2 76.49(10) . . ? N12 C26 C25 111.06(15) . . ? N12 C26 H26A 109.4 . . ? C25 C26 H26A 109.4 . . ? N12 C26 H26B 109.4 . . ? C25 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? N12 C27 H27A 109.5 . . ? N12 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N12 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C32 C28 C29 113.87(16) . . ? C32 C28 H28A 108.8 . . ? C29 C28 H28A 108.8 . . ? C32 C28 H28B 108.8 . . ? C29 C28 H28B 108.8 . . ? H28A C28 H28B 107.7 . . ? N12 C29 C28 112.62(16) . . ? N12 C29 C30 109.86(15) . . ? C28 C29 C30 108.92(16) . . ? N12 C29 H29A 108.4 . . ? C28 C29 H29A 108.4 . . ? C30 C29 H29A 108.4 . . ? O19 C30 O20 124.3(2) . . ? O19 C30 C29 124.7(2) . . ? O20 C30 C29 110.98(18) . . ? O20 C31 H31A 109.5 . . ? O20 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O20 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C34 C32 N13 108.85(16) . . ? C34 C32 C28 127.71(17) . . ? N13 C32 C28 123.43(16) . . ? N13 C33 N14 110.87(17) . . ? N13 C33 H33A 124.6 . . ? N14 C33 H33A 124.6 . . ? C32 C34 N14 107.07(16) . . ? C32 C34 H34A 126.5 . . ? N14 C34 H34A 126.5 . . ? O21 C35 C36 121.31(18) . . ? O21 C35 C40 119.99(17) . . ? C36 C35 C40 118.70(18) . . ? C37 C36 C35 121.03(19) . . ? C37 C36 H36A 119.5 . . ? C35 C36 H36A 119.5 . . ? C36 C37 C38 119.97(19) . . ? C36 C37 H37A 120.0 . . ? C38 C37 H37A 120.0 . . ? C37 C38 C39 119.62(19) . . ? C37 C38 H38A 120.2 . . ? C39 C38 H38A 120.2 . . ? C40 C39 C38 121.02(19) . . ? C40 C39 H39A 119.5 . . ? C38 C39 H39A 119.5 . . ? C39 C40 C35 119.61(18) . . ? C39 C40 N14 118.72(17) . . ? C35 C40 N14 121.63(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 O11 H11 O5 0.805(16) 1.932(17) 2.725(2) 168(3) . O21 H21 O2 0.791(16) 2.016(17) 2.796(2) 168(3) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.055 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.057 # Attachment 'tridentate_ether.CIF' data_mn1583 _database_code_depnum_ccdc_archive 'CCDC 640796' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (CuL)(ClO4) , L = 2-(S )-((2-pyridylmethyl)methylamino) -3-(1- (hydroxy)phenyl)-imidazol-4(5)-yl)- propyl methyl ether ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 Cl Cu N4 O2, Cl O4' _chemical_formula_sum 'C20 H24 Cl2 Cu N4 O6' _chemical_formula_weight 550.87 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' Cl Cl 0.1484 0.1585 '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 6.6563(11) _cell_length_b 16.198(3) _cell_length_c 20.176(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2175.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 980 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 20.0 _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1132 _exptl_absorpt_coefficient_mu 1.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.612 _exptl_absorpt_correction_T_max 0.926 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(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 1000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28893 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 30.03 _reflns_number_total 6365 _reflns_number_gt 5450 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART 5.054 (Bruker, 2002)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _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. All H atoms were riding with standard C-H distances set by the SHELXL software except for the hydroxyl H which was freely refined. ; _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^)+(0.0445P)^2^+1.0624P] 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 ? _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.026(11) _refine_ls_number_reflns 6365 _refine_ls_number_parameters 304 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 0.57894(4) 0.749194(18) 0.553471(13) 0.01121(7) Uani 1 1 d . . . Cl1 Cl 0.66585(9) 0.75825(4) 0.44425(3) 0.01389(11) Uani 1 1 d . . . O1 O 0.4623(3) 0.52408(11) 0.37457(9) 0.0175(4) Uani 1 1 d D . . H1 H 0.440(6) 0.524(2) 0.3353(10) 0.034(10) Uiso 1 1 d D . . O2 O 0.3174(3) 0.74956(14) 0.78443(8) 0.0194(4) Uani 1 1 d . . . N1 N 0.5954(3) 0.62813(12) 0.55013(10) 0.0128(4) Uani 1 1 d . . . N2 N 0.5583(4) 0.50277(13) 0.50935(10) 0.0135(4) Uani 1 1 d . . . N3 N 0.5698(3) 0.75366(13) 0.65706(9) 0.0124(3) Uani 1 1 d . . . N4 N 0.5643(3) 0.87197(12) 0.56214(10) 0.0124(4) Uani 1 1 d . . . C1 C 0.5102(4) 0.44701(15) 0.39578(13) 0.0149(5) Uani 1 1 d . . . C2 C 0.5176(4) 0.37909(16) 0.35331(13) 0.0178(5) Uani 1 1 d . . . H2 H 0.4856 0.3860 0.3078 0.021 Uiso 1 1 calc R . . C3 C 0.5707(5) 0.30186(16) 0.37651(14) 0.0211(5) Uani 1 1 d . . . H3 H 0.5733 0.2563 0.3469 0.025 Uiso 1 1 calc R . . C4 C 0.6202(5) 0.29027(16) 0.44247(15) 0.0234(6) Uani 1 1 d . . . H4 H 0.6578 0.2372 0.4582 0.028 Uiso 1 1 calc R . . C5 C 0.6139(5) 0.35754(17) 0.48546(14) 0.0207(6) Uani 1 1 d . . . H5 H 0.6481 0.3501 0.5308 0.025 Uiso 1 1 calc R . . C6 C 0.5582(4) 0.43549(15) 0.46288(12) 0.0138(5) Uani 1 1 d . . . C7 C 0.5922(4) 0.58319(16) 0.49514(12) 0.0132(5) Uani 1 1 d . . . H7 H 0.6110 0.6046 0.4517 0.016 Uiso 1 1 calc R . . C8 C 0.5397(4) 0.49650(16) 0.57751(13) 0.0164(5) Uani 1 1 d . . . H8 H 0.5150 0.4476 0.6021 0.020 Uiso 1 1 calc R . . C9 C 0.5638(4) 0.57414(15) 0.60251(12) 0.0140(5) Uani 1 1 d . . . C10 C 0.5673(4) 0.59911(15) 0.67319(12) 0.0149(5) Uani 1 1 d . . . H10A H 0.7091 0.6023 0.6877 0.018 Uiso 1 1 calc R . . H10B H 0.5017 0.5552 0.6996 0.018 Uiso 1 1 calc R . . C11 C 0.4655(4) 0.68106(15) 0.68954(12) 0.0134(5) Uani 1 1 d . . . H11 H 0.3254 0.6787 0.6718 0.016 Uiso 1 1 calc R . . C12 C 0.4513(4) 0.68704(16) 0.76494(12) 0.0171(5) Uani 1 1 d . . . H12A H 0.4053 0.6335 0.7831 0.021 Uiso 1 1 calc R . . H12B H 0.5861 0.6987 0.7834 0.021 Uiso 1 1 calc R . . C13 C 0.3645(5) 0.78278(19) 0.84779(14) 0.0240(6) Uani 1 1 d . . . H13A H 0.2718 0.8280 0.8580 0.036 Uiso 1 1 calc R . . H13B H 0.5026 0.8037 0.8476 0.036 Uiso 1 1 calc R . . H13C H 0.3514 0.7395 0.8815 0.036 Uiso 1 1 calc R . . C14 C 0.4627(4) 0.83198(15) 0.67325(12) 0.0137(5) Uani 1 1 d . . . H14A H 0.5067 0.8518 0.7174 0.016 Uiso 1 1 calc R . . H14B H 0.3164 0.8213 0.6753 0.016 Uiso 1 1 calc R . . C15 C 0.5038(4) 0.89747(15) 0.62242(12) 0.0131(5) Uani 1 1 d . . . C16 C 0.4700(4) 0.98061(16) 0.63650(12) 0.0152(5) Uani 1 1 d . . . H16 H 0.4278 0.9974 0.6794 0.018 Uiso 1 1 calc R . . C17 C 0.4992(4) 1.03831(16) 0.58662(13) 0.0153(5) Uani 1 1 d . . . H17 H 0.4773 1.0953 0.5950 0.018 Uiso 1 1 calc R . . C18 C 0.5607(5) 1.01196(15) 0.52445(13) 0.0171(5) Uani 1 1 d . . . H18 H 0.5807 1.0506 0.4896 0.020 Uiso 1 1 calc R . . C19 C 0.5925(4) 0.92876(16) 0.51391(13) 0.0156(5) Uani 1 1 d . . . H19 H 0.6355 0.9108 0.4714 0.019 Uiso 1 1 calc R . . C20 C 0.7849(4) 0.76205(18) 0.67739(13) 0.0182(6) Uani 1 1 d . . . H20A H 0.7928 0.7687 0.7256 0.027 Uiso 1 1 calc R . . H20B H 0.8438 0.8105 0.6557 0.027 Uiso 1 1 calc R . . H20C H 0.8591 0.7124 0.6642 0.027 Uiso 1 1 calc R . . Cl2 Cl 0.43748(10) 0.53364(4) 0.19412(3) 0.01746(13) Uani 1 1 d . . . O3 O 0.4329(3) 0.45344(12) 0.16362(11) 0.0277(5) Uani 1 1 d . . . O4 O 0.3835(4) 0.59516(14) 0.14680(12) 0.0389(6) Uani 1 1 d . . . O5 O 0.6330(3) 0.55052(14) 0.22168(11) 0.0298(5) Uani 1 1 d . . . O6 O 0.2949(3) 0.53386(16) 0.24909(11) 0.0316(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01476(13) 0.00940(12) 0.00947(12) -0.00001(12) 0.00075(10) 0.00004(14) Cl1 0.0176(3) 0.0136(3) 0.0106(2) -0.0002(2) 0.0014(2) -0.0001(2) O1 0.0231(10) 0.0146(8) 0.0150(9) -0.0026(7) -0.0035(8) 0.0034(8) O2 0.0238(9) 0.0202(9) 0.0141(8) -0.0024(9) 0.0028(6) 0.0055(10) N1 0.0134(10) 0.0137(9) 0.0113(9) 0.0006(8) 0.0008(9) 0.0001(8) N2 0.0145(11) 0.0115(9) 0.0144(9) -0.0013(7) 0.0003(9) -0.0003(9) N3 0.0135(8) 0.0112(9) 0.0124(8) -0.0002(8) -0.0002(7) -0.0009(11) N4 0.0120(10) 0.0127(9) 0.0124(9) -0.0009(7) -0.0004(8) -0.0003(8) C1 0.0111(11) 0.0144(11) 0.0193(12) -0.0016(9) 0.0021(9) -0.0018(9) C2 0.0177(13) 0.0180(12) 0.0179(12) -0.0038(10) 0.0004(10) -0.0026(10) C3 0.0222(13) 0.0148(12) 0.0262(13) -0.0059(10) 0.0057(12) -0.0023(11) C4 0.0328(16) 0.0101(11) 0.0274(14) -0.0005(11) 0.0075(13) -0.0005(11) C5 0.0289(16) 0.0154(12) 0.0177(12) 0.0007(10) 0.0021(12) -0.0009(11) C6 0.0152(11) 0.0109(11) 0.0155(11) -0.0016(8) 0.0032(9) -0.0017(10) C7 0.0137(13) 0.0125(11) 0.0134(11) 0.0004(8) 0.0010(9) 0.0008(11) C8 0.0212(14) 0.0133(11) 0.0148(11) 0.0010(9) 0.0034(10) 0.0026(10) C9 0.0162(11) 0.0134(11) 0.0125(10) 0.0013(9) -0.0003(10) 0.0003(10) C10 0.0199(12) 0.0124(11) 0.0125(10) 0.0013(8) 0.0001(10) 0.0039(10) C11 0.0145(12) 0.0144(11) 0.0112(10) 0.0000(9) 0.0014(9) -0.0017(10) C12 0.0222(14) 0.0158(12) 0.0134(11) 0.0018(9) 0.0003(10) 0.0029(11) C13 0.0303(15) 0.0229(14) 0.0188(13) -0.0050(11) 0.0035(12) -0.0015(12) C14 0.0166(13) 0.0125(11) 0.0120(10) -0.0003(9) 0.0019(9) 0.0014(10) C15 0.0118(11) 0.0128(11) 0.0145(11) -0.0002(9) -0.0002(9) -0.0012(9) C16 0.0156(12) 0.0140(11) 0.0159(11) -0.0034(9) -0.0013(9) -0.0021(10) C17 0.0158(11) 0.0099(11) 0.0202(12) -0.0009(9) -0.0009(10) -0.0019(10) C18 0.0182(13) 0.0120(11) 0.0211(12) 0.0028(9) -0.0030(12) -0.0019(11) C19 0.0169(13) 0.0154(12) 0.0144(11) 0.0020(9) 0.0006(11) -0.0007(11) C20 0.0165(12) 0.0198(15) 0.0183(12) 0.0018(11) -0.0008(9) -0.0029(11) Cl2 0.0204(3) 0.0146(3) 0.0174(3) -0.0013(2) 0.0008(2) -0.0002(2) O3 0.0275(11) 0.0206(10) 0.0351(11) -0.0135(9) -0.0024(10) 0.0002(9) O4 0.0560(17) 0.0266(11) 0.0340(12) 0.0125(10) -0.0181(12) -0.0079(12) O5 0.0275(11) 0.0284(12) 0.0336(12) -0.0052(9) -0.0112(10) -0.0021(10) O6 0.0283(12) 0.0398(14) 0.0266(11) -0.0074(10) 0.0058(9) 0.0005(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 N1 1.965(2) . ? Cu1 N4 1.999(2) . ? Cu1 N3 2.0921(18) . ? Cu1 Cl1 2.2829(7) . ? Cu1 Cl1 2.7527(8) 4_466 ? Cl1 Cu1 2.7527(8) 4_566 ? O1 C1 1.358(3) . ? O1 H1 0.807(18) . ? O2 C12 1.405(3) . ? O2 C13 1.422(3) . ? N1 C7 1.327(3) . ? N1 C9 1.388(3) . ? N2 C7 1.353(3) . ? N2 C8 1.384(3) . ? N2 C6 1.438(3) . ? N3 C14 1.491(3) . ? N3 C20 1.496(3) . ? N3 C11 1.515(3) . ? N4 C15 1.346(3) . ? N4 C19 1.352(3) . ? C1 C2 1.395(4) . ? C1 C6 1.403(4) . ? C2 C3 1.382(4) . ? C2 H2 0.9500 . ? C3 C4 1.384(4) . ? C3 H3 0.9500 . ? C4 C5 1.393(4) . ? C4 H4 0.9500 . ? C5 C6 1.393(4) . ? C5 H5 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.365(3) . ? C8 H8 0.9500 . ? C9 C10 1.482(3) . ? C10 C11 1.526(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.527(3) . ? C11 H11 1.0000 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.501(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.395(3) . ? C16 C17 1.387(4) . ? C16 H16 0.9500 . ? C17 C18 1.387(4) . ? C17 H17 0.9500 . ? C18 C19 1.381(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? Cl2 O4 1.426(2) . ? Cl2 O3 1.4378(19) . ? Cl2 O5 1.441(2) . ? Cl2 O6 1.460(2) . ? 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 N1 Cu1 N4 176.92(8) . . ? N1 Cu1 N3 94.04(8) . . ? N4 Cu1 N3 82.92(8) . . ? N1 Cu1 Cl1 90.97(6) . . ? N4 Cu1 Cl1 91.88(6) . . ? N3 Cu1 Cl1 165.79(6) . . ? N1 Cu1 Cl1 90.71(7) . 4_466 ? N4 Cu1 Cl1 89.63(7) . 4_466 ? N3 Cu1 Cl1 87.46(6) . 4_466 ? Cl1 Cu1 Cl1 105.78(2) . 4_466 ? Cu1 Cl1 Cu1 103.54(2) . 4_566 ? C1 O1 H1 110(3) . . ? C12 O2 C13 112.6(2) . . ? C7 N1 C9 106.8(2) . . ? C7 N1 Cu1 125.12(17) . . ? C9 N1 Cu1 126.46(17) . . ? C7 N2 C8 107.2(2) . . ? C7 N2 C6 126.3(2) . . ? C8 N2 C6 126.3(2) . . ? C14 N3 C20 108.7(2) . . ? C14 N3 C11 110.29(18) . . ? C20 N3 C11 113.0(2) . . ? C14 N3 Cu1 105.20(14) . . ? C20 N3 Cu1 104.43(14) . . ? C11 N3 Cu1 114.76(14) . . ? C15 N4 C19 118.9(2) . . ? C15 N4 Cu1 113.51(16) . . ? C19 N4 Cu1 127.39(17) . . ? O1 C1 C2 122.7(2) . . ? O1 C1 C6 118.7(2) . . ? C2 C1 C6 118.7(2) . . ? C3 C2 C1 121.0(3) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.6(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.0(2) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 120.9(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 119.8(2) . . ? C5 C6 N2 118.3(2) . . ? C1 C6 N2 121.9(2) . . ? N1 C7 N2 110.7(2) . . ? N1 C7 H7 124.6 . . ? N2 C7 H7 124.6 . . ? C9 C8 N2 106.8(2) . . ? C9 C8 H8 126.6 . . ? N2 C8 H8 126.6 . . ? C8 C9 N1 108.5(2) . . ? C8 C9 C10 127.5(2) . . ? N1 C9 C10 123.9(2) . . ? C9 C10 C11 116.0(2) . . ? C9 C10 H10A 108.3 . . ? C11 C10 H10A 108.3 . . ? C9 C10 H10B 108.3 . . ? C11 C10 H10B 108.3 . . ? H10A C10 H10B 107.4 . . ? N3 C11 C10 112.2(2) . . ? N3 C11 C12 114.2(2) . . ? C10 C11 C12 107.3(2) . . ? N3 C11 H11 107.6 . . ? C10 C11 H11 107.6 . . ? C12 C11 H11 107.6 . . ? O2 C12 C11 111.3(2) . . ? O2 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? O2 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 C15 111.4(2) . . ? N3 C14 H14A 109.4 . . ? C15 C14 H14A 109.4 . . ? N3 C14 H14B 109.4 . . ? C15 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? N4 C15 C16 121.9(2) . . ? N4 C15 C14 117.1(2) . . ? C16 C15 C14 120.9(2) . . ? C17 C16 C15 118.7(2) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 119.3(2) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C19 C18 C17 119.0(2) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? N4 C19 C18 122.1(2) . . ? N4 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? 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 . . ? O4 Cl2 O3 109.85(14) . . ? O4 Cl2 O5 110.69(15) . . ? O3 Cl2 O5 110.83(14) . . ? O4 Cl2 O6 110.06(16) . . ? O3 Cl2 O6 108.28(14) . . ? O5 Cl2 O6 107.07(14) . . ? 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 O1 H1 O6 0.807(18) 1.99(2) 2.771(3) 161(4) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.755 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.091