# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _publ_contact_author_email malcolmh@chem.leeds.ac.uk _publ_contact_author_name 'Dr. Malcolm A. Halcrow' _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_address ; Department of Chemistry University of Leeds Woodhouse Lane Leeds LS2 9JT UK ; _publ_contact_author_phone '+44 (0)113 3436506' _publ_contact_author_fax '+44 (0)113 3436565' _publ_section_title ; Temperature dependence of the electronic ground states of two mononuclear, six-coordinate copper(II) centres ; loop_ _publ_author_name _publ_author_address 'Malcolm A. Halcrow' ; Department of Chemistry, University of Leeds, Woodhouse Lane, Leeds LS2 9JT, UK ; 'Colin A. Kilner' ; Department of Chemistry, University of Leeds, Woodhouse Lane, Leeds LS2 9JT, UK ; 'Joanne Wolowska' ; CW EPR Service Centre. Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK ; 'Eric J. L. McInnes' ; CW EPR Service Centre, Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK ; 'Adam J. Bridgeman' ; Department of Chemistry, University of Hull, Kingston-upon-Hull HU6 7RX, UK ; #================================================================= data_mh59 _database_code_depnum_ccdc_archive 'CCDC 217086' _chemical_name_common ; Bis(2,6-bis(hydrazonomethyl)pyridine)copper(ii) diperchlorate bis-acetone solvate ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis[2,6-bis{hydrazonomethyl}pyridine]copper(II) diperchlorate bis-acetone solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 Cu N10, 2[Cl O4], 2[C3 H6 O]' _chemical_formula_sum 'C20 H30 Cl2 Cu N10 O10' _chemical_formula_weight 704.98 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 21.8166(4) _cell_length_b 7.3939(1) _cell_length_c 21.5138(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.0158(7) _cell_angle_gamma 90.00 _cell_volume 3063.71(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25996 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 27.51 _exptl_crystal_description Plate _exptl_crystal_colour Green _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1452 _exptl_absorpt_coefficient_mu 0.954 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.855 _exptl_absorpt_correction_T_max 0.954 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD diffractometer' _diffrn_measurement_method 'Area detector scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25996 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.51 _reflns_number_total 6988 _reflns_number_gt 6373 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _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. One ClO~4~^-^ anion is disordered over two orientations sharing one O atom O32: Cl31A, O32, O33A-O35A, occupancy 0.75 Cl31B, O32, O33B-O35B, occupancy 0.25. All Cl-O bonds within this anion were restrained to 1.43(2)\%A, and non-bonded O...O distances within a given disorder orientation to 2.34(2)\%A. All non-H atoms with occupancy >0.5 were refined anisotropically. Attempts to locate H atoms in the Fourier difference map were unsuccessful. All C-bound H atoms were placed in calculated positions, and refined using a riding model. All NH~2~ H atoms were placed in calculated positions, then allowed to refine with a common thermal parameter subject to the restraints N-H = 0.92(2)\%A and H...H = 1.50(2)\%A. There are two residual electron density peaks of 1.2 e.A^-3^, lying 2.2\%A from O41 (an acetone O atom), and 1.7\%A from N12 and N13, respectively. These each correspond to ca. 0.15 of an O atom. However, given their proximity to other, fully occupied atoms in the lattice there is no chemically reasonable interpretation that would allow these residual peaks to be included in the final model. ; _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^)+(0.0849P)^2^+2.9651P] 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 SHELXL _refine_ls_extinction_coef 0.0051(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.004(13) _refine_ls_number_reflns 6988 _refine_ls_number_parameters 436 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1382 _refine_ls_wR_factor_gt 0.1317 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.062 _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 0.52198(2) 0.44904(5) 0.41845(2) 0.03311(14) Uani 1 1 d . . . N2 N 0.6066(2) 0.4448(4) 0.5059(2) 0.0378(8) Uani 1 1 d . . . C3 C 0.6527(2) 0.5787(6) 0.5211(3) 0.0416(9) Uani 1 1 d . . . C4 C 0.7146(3) 0.5796(7) 0.5841(3) 0.0502(11) Uani 1 1 d . . . H4 H 0.7479 0.6730 0.5944 0.060 Uiso 1 1 calc R . . C5 C 0.7263(3) 0.4384(8) 0.6317(3) 0.0591(15) Uani 1 1 d . . . H5 H 0.7675 0.4368 0.6756 0.071 Uiso 1 1 calc R . . C6 C 0.6791(3) 0.3047(7) 0.6154(3) 0.0542(11) Uani 1 1 d . . . H6 H 0.6874 0.2079 0.6474 0.065 Uiso 1 1 calc R . . C7 C 0.6185(2) 0.3089(6) 0.5517(2) 0.0429(9) Uani 1 1 d . . . C8 C 0.6312(2) 0.7191(6) 0.4666(2) 0.0416(9) Uani 1 1 d . . . H8 H 0.6585 0.8238 0.4722 0.050 Uiso 1 1 calc R . . N9 N 0.57271(18) 0.6920(5) 0.4105(2) 0.0405(7) Uani 1 1 d . . . N10 N 0.5490(3) 0.8067(7) 0.3566(3) 0.0659(13) Uani 1 1 d D . . H10A H 0.5038(17) 0.796(7) 0.322(2) 0.053(5) Uiso 1 1 d D . . H10B H 0.563(2) 0.923(4) 0.365(3) 0.053(5) Uiso 1 1 d D . . C11 C 0.5624(3) 0.1738(6) 0.5262(3) 0.0481(10) Uani 1 1 d . . . H11 H 0.5654 0.0685 0.5528 0.058 Uiso 1 1 calc R . . N12 N 0.5096(2) 0.2044(5) 0.4670(2) 0.0440(8) Uani 1 1 d . . . N13 N 0.4569(3) 0.0851(7) 0.4384(3) 0.0689(14) Uani 1 1 d D . . H13A H 0.4116(17) 0.111(7) 0.406(2) 0.053(5) Uiso 1 1 d D . . H13B H 0.459(3) -0.010(6) 0.467(3) 0.053(5) Uiso 1 1 d D . . N14 N 0.43613(19) 0.4614(4) 0.3286(2) 0.0340(7) Uani 1 1 d . . . C15 C 0.3810(2) 0.5551(5) 0.3247(3) 0.0411(10) Uani 1 1 d . . . C16 C 0.3214(3) 0.5743(7) 0.2602(3) 0.0501(12) Uani 1 1 d . . . H16 H 0.2827 0.6401 0.2574 0.060 Uiso 1 1 calc R . . C17 C 0.3187(2) 0.4988(8) 0.2014(3) 0.0507(11) Uani 1 1 d . . . H17 H 0.2784 0.5133 0.1572 0.061 Uiso 1 1 calc R . . C18 C 0.3754(3) 0.3995(7) 0.2058(3) 0.0489(10) Uani 1 1 d . . . H18 H 0.3736 0.3438 0.1652 0.059 Uiso 1 1 calc R . . C19 C 0.4340(2) 0.3843(5) 0.2706(2) 0.0399(8) Uani 1 1 d . . . C20 C 0.3896(2) 0.6331(6) 0.3894(3) 0.0448(10) Uani 1 1 d . . . H20 H 0.3523 0.6934 0.3916 0.054 Uiso 1 1 calc R . . N21 N 0.44886(19) 0.6193(5) 0.4439(2) 0.0410(7) Uani 1 1 d . . . N22 N 0.4599(2) 0.7036(6) 0.5052(2) 0.0522(9) Uani 1 1 d D . . H22A H 0.4978(19) 0.646(8) 0.541(2) 0.053(5) Uiso 1 1 d D . . H22B H 0.423(2) 0.698(7) 0.516(3) 0.053(5) Uiso 1 1 d D . . C23 C 0.4961(2) 0.2877(5) 0.2810(2) 0.0401(8) Uani 1 1 d . . . H23 H 0.4984 0.2294 0.2428 0.048 Uiso 1 1 calc R . . N24 N 0.54726(18) 0.2832(4) 0.34261(18) 0.0364(7) Uani 1 1 d . . . N25 N 0.6059(2) 0.1859(5) 0.3554(2) 0.0453(8) Uani 1 1 d D . . H25A H 0.646(2) 0.213(8) 0.3966(17) 0.053(5) Uiso 1 1 d D . . H25B H 0.616(2) 0.201(8) 0.3183(19) 0.053(5) Uiso 1 1 d D . . Cl26 Cl 0.61731(5) 0.22227(13) 0.18176(5) 0.0394(2) Uani 1 1 d . . . O27 O 0.6668(2) 0.2698(6) 0.2529(2) 0.0709(11) Uani 1 1 d . . . O28 O 0.5865(2) 0.3824(6) 0.1428(2) 0.0678(10) Uani 1 1 d . . . O29 O 0.5651(2) 0.1047(6) 0.1832(3) 0.0749(12) Uani 1 1 d . . . O30 O 0.65312(18) 0.1279(5) 0.15035(19) 0.0533(8) Uani 1 1 d . . . O32 O 0.7615(2) 0.0479(6) 0.4268(2) 0.0684(12) Uani 1 1 d D . . Cl31A Cl 0.77971(17) 0.0731(7) 0.49900(16) 0.0353(9) Uani 0.75 1 d PD A 1 O33A O 0.7226(3) 0.1473(10) 0.5050(3) 0.0706(16) Uani 0.75 1 d PD A 1 O34A O 0.8366(3) 0.1959(9) 0.5323(3) 0.0583(14) Uani 0.75 1 d PD A 1 O35A O 0.7965(4) -0.0977(7) 0.5334(3) 0.0724(16) Uani 0.75 1 d PD A 1 Cl31B Cl 0.7812(8) 0.094(2) 0.4984(8) 0.056(6) Uiso 0.25 1 d PD A 2 O33B O 0.8525(7) 0.135(3) 0.5401(9) 0.058(6) Uiso 0.25 1 d PD A 2 O34B O 0.7628(12) -0.037(3) 0.5363(10) 0.095(7) Uiso 0.25 1 d PD A 2 O35B O 0.7403(10) 0.257(2) 0.4928(10) 0.088(6) Uiso 0.25 1 d PD A 2 O36 O 0.4318(2) 0.8486(6) 0.2154(2) 0.0660(10) Uani 1 1 d . . . C37 C 0.4403(3) 0.8231(6) 0.1638(3) 0.0480(11) Uani 1 1 d . . . C38 C 0.4030(4) 0.9334(10) 0.0996(4) 0.0790(19) Uani 1 1 d . . . H38A H 0.3977 0.8640 0.0586 0.095 Uiso 1 1 calc R . . H38B H 0.4295 1.0438 0.1038 0.095 Uiso 1 1 calc R . . H38C H 0.3571 0.9655 0.0939 0.095 Uiso 1 1 calc R . . C39 C 0.4881(4) 0.6798(8) 0.1640(4) 0.0679(14) Uani 1 1 d . . . H39A H 0.5210 0.7320 0.1499 0.081 Uiso 1 1 calc R . . H39B H 0.4612 0.5842 0.1308 0.081 Uiso 1 1 calc R . . H39C H 0.5136 0.6286 0.2114 0.081 Uiso 1 1 calc R . . O40 O 0.3094(3) 0.1711(9) 0.3291(4) 0.0971(17) Uani 1 1 d . . . C41 C 0.2586(3) 0.1582(8) 0.3387(3) 0.0608(13) Uani 1 1 d . . . C42 C 0.2665(4) 0.0510(8) 0.4001(4) 0.0653(16) Uani 1 1 d . . . H42A H 0.2918 -0.0609 0.4029 0.098 Uiso 1 1 calc R . . H42B H 0.2205 0.0214 0.3949 0.098 Uiso 1 1 calc R . . H42C H 0.2925 0.1216 0.4433 0.098 Uiso 1 1 calc R . . C43 C 0.1915(4) 0.2431(10) 0.2944(4) 0.083(2) Uani 1 1 d . . . H43A H 0.1775 0.3151 0.3239 0.124 Uiso 1 1 calc R . . H43B H 0.1566 0.1494 0.2699 0.124 Uiso 1 1 calc R . . H43C H 0.1953 0.3219 0.2598 0.124 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 0.0357(2) 0.0287(2) 0.0375(2) 0.00291(18) 0.01928(17) -0.00061(18) N2 0.039(2) 0.0334(19) 0.041(2) 0.0039(13) 0.0186(17) 0.0040(12) C3 0.041(2) 0.041(2) 0.045(2) -0.0021(17) 0.0217(19) 0.0036(16) C4 0.041(2) 0.050(3) 0.050(3) -0.009(2) 0.013(2) 0.001(2) C5 0.050(3) 0.075(4) 0.040(3) 0.001(2) 0.010(2) 0.018(2) C6 0.062(3) 0.054(3) 0.048(2) 0.012(2) 0.027(2) 0.016(2) C7 0.051(2) 0.040(2) 0.040(2) 0.0062(16) 0.0230(19) 0.0081(17) C8 0.041(2) 0.036(2) 0.050(2) 0.0003(16) 0.0237(19) -0.0059(15) N9 0.0411(18) 0.0350(17) 0.0483(19) 0.0051(14) 0.0235(16) -0.0027(13) N10 0.063(3) 0.051(2) 0.061(3) 0.024(2) 0.011(2) -0.013(2) C11 0.060(3) 0.040(2) 0.056(3) 0.0165(19) 0.037(2) 0.0108(19) N12 0.053(2) 0.0339(17) 0.052(2) 0.0034(15) 0.0302(18) -0.0021(15) N13 0.058(3) 0.048(2) 0.096(4) 0.015(2) 0.032(3) -0.014(2) N14 0.0371(19) 0.0294(17) 0.042(2) 0.0014(12) 0.0238(16) -0.0017(12) C15 0.035(2) 0.038(2) 0.054(3) 0.0027(16) 0.0237(19) -0.0018(15) C16 0.032(2) 0.047(3) 0.063(3) 0.005(2) 0.016(2) -0.0019(17) C17 0.037(2) 0.052(2) 0.050(3) 0.005(2) 0.010(2) -0.0067(19) C18 0.048(2) 0.047(2) 0.041(2) 0.0025(18) 0.0118(19) -0.0073(19) C19 0.045(2) 0.0294(18) 0.042(2) 0.0072(15) 0.0171(18) -0.0006(15) C20 0.040(2) 0.040(2) 0.066(3) -0.0037(18) 0.035(2) -0.0012(16) N21 0.0443(19) 0.0357(17) 0.052(2) -0.0039(14) 0.0300(17) -0.0061(14) N22 0.060(2) 0.053(2) 0.054(2) -0.0113(18) 0.035(2) -0.0095(19) C23 0.050(2) 0.0369(19) 0.039(2) -0.0040(15) 0.0258(18) -0.0019(16) N24 0.0388(17) 0.0349(16) 0.0409(17) 0.0058(13) 0.0231(15) 0.0030(13) N25 0.045(2) 0.0416(19) 0.057(2) 0.0093(16) 0.0304(18) 0.0088(15) Cl26 0.0402(5) 0.0395(5) 0.0407(5) -0.0038(4) 0.0208(4) -0.0002(4) O27 0.079(3) 0.072(3) 0.046(2) -0.0132(17) 0.0158(19) -0.002(2) O28 0.064(2) 0.055(2) 0.078(3) 0.0117(18) 0.028(2) 0.0185(18) O29 0.074(3) 0.061(2) 0.115(4) -0.008(2) 0.065(3) -0.021(2) O30 0.0490(19) 0.055(2) 0.059(2) -0.0124(16) 0.0278(16) 0.0041(15) O32 0.067(3) 0.094(4) 0.046(2) -0.0166(19) 0.028(2) -0.006(2) Cl31A 0.0307(12) 0.0388(12) 0.0329(13) 0.0004(6) 0.0121(7) -0.0068(7) O33A 0.042(3) 0.101(5) 0.069(3) -0.027(3) 0.027(2) 0.007(3) O34A 0.042(3) 0.057(3) 0.072(4) -0.009(3) 0.024(3) -0.018(3) O35A 0.088(4) 0.040(2) 0.075(4) 0.018(2) 0.026(3) 0.002(3) O36 0.071(2) 0.066(2) 0.066(2) -0.0008(18) 0.036(2) 0.0012(19) C37 0.053(3) 0.032(2) 0.051(3) 0.0011(17) 0.019(2) -0.0080(18) C38 0.058(3) 0.094(5) 0.062(4) 0.021(3) 0.010(3) -0.003(3) C39 0.073(4) 0.054(3) 0.086(4) 0.006(3) 0.045(3) 0.006(3) O40 0.085(4) 0.116(5) 0.109(4) 0.015(3) 0.060(3) 0.003(3) C41 0.078(4) 0.051(3) 0.067(3) -0.009(2) 0.045(3) -0.002(3) C42 0.075(4) 0.058(3) 0.060(3) 0.001(2) 0.029(3) 0.008(3) C43 0.091(5) 0.078(4) 0.050(3) -0.003(3) 0.010(3) 0.021(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.921(4) . ? Cu1 N14 1.962(4) . ? Cu1 N9 2.159(3) . ? Cu1 N12 2.168(4) . ? Cu1 N21 2.291(4) . ? Cu1 N24 2.305(3) . ? N2 C3 1.337(6) . ? N2 C7 1.343(5) . ? C3 C4 1.394(7) . ? C3 C8 1.468(6) . ? C4 C5 1.399(8) . ? C5 C6 1.349(8) . ? C6 C7 1.387(7) . ? C7 C11 1.472(7) . ? C8 N9 1.296(6) . ? N9 N10 1.329(5) . ? C11 N12 1.274(7) . ? N12 N13 1.347(6) . ? N14 C19 1.354(6) . ? N14 C15 1.356(6) . ? C15 C16 1.393(7) . ? C15 C20 1.435(7) . ? C16 C17 1.359(8) . ? C17 C18 1.403(8) . ? C18 C19 1.384(6) . ? C19 C23 1.452(6) . ? C20 N21 1.277(6) . ? N21 N22 1.374(5) . ? C23 N24 1.270(6) . ? N24 N25 1.378(5) . ? Cl26 O28 1.424(4) . ? Cl26 O30 1.432(3) . ? Cl26 O27 1.441(4) . ? Cl26 O29 1.445(4) . ? Cl31A O33A 1.422(6) . ? Cl31A O32 1.423(5) . ? Cl31A O35A 1.422(7) . ? Cl31A O34A 1.429(5) . ? Cl31B O33B 1.414(16) . ? Cl31B O32 1.432(15) . ? Cl31B O34B 1.442(16) . ? Cl31B O35B 1.465(17) . ? O36 C37 1.224(7) . ? C37 C38 1.475(8) . ? C37 C39 1.486(8) . ? O40 C41 1.220(8) . ? C41 C43 1.462(9) . ? C41 C42 1.481(9) . ? 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 N2 Cu1 N14 178.17(14) . . ? N2 Cu1 N9 78.38(14) . . ? N14 Cu1 N9 99.83(13) . . ? N2 Cu1 N12 78.14(15) . . ? N14 Cu1 N12 103.64(15) . . ? N9 Cu1 N12 156.52(16) . . ? N2 Cu1 N21 103.40(15) . . ? N14 Cu1 N21 76.11(14) . . ? N9 Cu1 N21 90.14(13) . . ? N12 Cu1 N21 94.89(14) . . ? N2 Cu1 N24 104.20(14) . . ? N14 Cu1 N24 76.28(14) . . ? N9 Cu1 N24 94.82(13) . . ? N12 Cu1 N24 91.28(13) . . ? N21 Cu1 N24 152.39(13) . . ? C3 N2 C7 120.7(4) . . ? C3 N2 Cu1 119.6(3) . . ? C7 N2 Cu1 119.7(3) . . ? N2 C3 C4 121.0(5) . . ? N2 C3 C8 114.0(4) . . ? C4 C3 C8 125.0(5) . . ? C3 C4 C5 117.9(5) . . ? C6 C5 C4 120.1(5) . . ? C5 C6 C7 119.8(5) . . ? N2 C7 C6 120.5(5) . . ? N2 C7 C11 113.2(4) . . ? C6 C7 C11 126.3(4) . . ? N9 C8 C3 116.1(4) . . ? C8 N9 N10 121.6(4) . . ? C8 N9 Cu1 111.8(3) . . ? N10 N9 Cu1 126.6(3) . . ? N12 C11 C7 117.1(4) . . ? C11 N12 N13 121.2(4) . . ? C11 N12 Cu1 111.8(3) . . ? N13 N12 Cu1 126.8(3) . . ? C19 N14 C15 120.9(4) . . ? C19 N14 Cu1 119.5(3) . . ? C15 N14 Cu1 119.6(3) . . ? N14 C15 C16 120.0(5) . . ? N14 C15 C20 115.9(4) . . ? C16 C15 C20 124.1(4) . . ? C17 C16 C15 119.8(5) . . ? C16 C17 C18 120.0(5) . . ? C19 C18 C17 118.7(5) . . ? N14 C19 C18 120.6(4) . . ? N14 C19 C23 116.1(4) . . ? C18 C19 C23 123.3(4) . . ? N21 C20 C15 118.3(4) . . ? C20 N21 N22 119.4(4) . . ? C20 N21 Cu1 110.0(3) . . ? N22 N21 Cu1 130.6(3) . . ? N24 C23 C19 118.2(4) . . ? C23 N24 N25 120.0(4) . . ? C23 N24 Cu1 109.8(3) . . ? N25 N24 Cu1 130.1(3) . . ? O28 Cl26 O30 109.8(3) . . ? O28 Cl26 O27 109.5(3) . . ? O30 Cl26 O27 108.5(3) . . ? O28 Cl26 O29 110.7(3) . . ? O30 Cl26 O29 109.1(2) . . ? O27 Cl26 O29 109.2(3) . . ? O33A Cl31A O35A 108.5(5) . . ? O33A Cl31A O32 110.0(4) . . ? O35A Cl31A O32 108.8(5) . . ? O33A Cl31A O34A 107.6(5) . . ? O35A Cl31A O34A 110.7(5) . . ? O32 Cl31A O34A 111.2(4) . . ? O33B Cl31B O32 114.7(13) . . ? O33B Cl31B O34B 107.3(13) . . ? O32 Cl31B O34B 115.0(13) . . ? O33B Cl31B O35B 109.0(13) . . ? O32 Cl31B O35B 104.2(12) . . ? O34B Cl31B O35B 106.1(13) . . ? O36 C37 C38 120.8(6) . . ? O36 C37 C39 120.9(5) . . ? C38 C37 C39 118.3(6) . . ? O40 C41 C43 124.6(7) . . ? O40 C41 C42 117.3(7) . . ? C43 C41 C42 118.2(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N10 H10A O36 0.92(3) 2.12(4) 2.927(6) 146(5) . N10 H10B N25 0.91(3) 2.21(3) 3.071(6) 160(6) 1_565 N13 H13A O40 0.92(3) 2.11(3) 3.029(8) 178(5) . N13 H13B N22 0.92(3) 2.27(3) 3.153(7) 161(5) 1_545 N22 H22A O28 0.93(3) 2.15(4) 3.018(7) 156(5) 2_565 N22 H22B O34A 0.93(3) 2.08(3) 3.009(7) 176(4) 3_455 N22 H22B O33B 0.93(3) 1.91(3) 2.823(18) 168(5) 3_455 N25 H25A O32 0.93(3) 2.60(5) 3.166(6) 120(4) . N25 H25A O33A 0.93(3) 2.19(3) 3.037(7) 151(5) . N25 H25A O35B 0.93(3) 2.15(4) 3.08(2) 176(5) . N25 H25B O27 0.93(3) 2.22(3) 3.125(6) 165(4) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.184 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.154 #=END data_mh68300 _database_code_depnum_ccdc_archive 'CCDC 217087' _chemical_name_common ;Bis(2,6-bis(oximomethyl)pyridine)copper(ii) diperchlorate bis- acetone solvate ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis[2,6-bis{oximomethyl}pyridine]copper(II) diperchlorate bis-acetone solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Cu N6 O4, 2[Cl O4], 2[C3 H6 O]' _chemical_formula_sum 'C20 H26 Cl2 Cu N6 O14' _chemical_formula_weight 708.91 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1602(1) _cell_length_b 13.2144(3) _cell_length_c 17.3567(3) _cell_angle_alpha 107.6773(12) _cell_angle_beta 95.9665(13) _cell_angle_gamma 103.6906(8) _cell_volume 1492.58(5) _cell_formula_units_Z 2 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 23705 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 27.50 _exptl_crystal_description Prism _exptl_crystal_colour Green _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 726 _exptl_absorpt_coefficient_mu 0.986 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.628 _exptl_absorpt_correction_T_max 0.827 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV. See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 'Nonius KappaCCD diffractometer' _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23705 _diffrn_reflns_av_R_equivalents 0.0856 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6797 _reflns_number_gt 5086 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _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. The ClO~4~^-^ anion Cl31-O35 is disordered, and was modelled over three orientations: Cl31A-O35A, occupancy 0.20 Cl31B-O35B, occupancy 0.40 Cl31C-O35C, occupancy 0.40 All disordered Cl-O bonds were restrained to 1.41(2)%A, and non-bonded O...O distances within a given disorder orientation were restrained to 2.30(2)\%A. All non-H atoms except for the disordered anion were refined anisotropically, while all H atoms were placed in calculated positions and refined using a riding model. ; _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^)+(0.1261P)^2^+0.2933P] 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 SHELXL _refine_ls_extinction_coef 0.045(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6797 _refine_ls_number_parameters 415 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.0633 _refine_ls_wR_factor_ref 0.1979 _refine_ls_wR_factor_gt 0.1782 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.061 _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 0.35175(5) 0.57359(3) 0.26302(2) 0.0482(2) Uani 1 1 d . . . N2 N 0.4824(4) 0.7307(2) 0.30273(17) 0.0505(6) Uani 1 1 d . . . C3 C 0.6556(5) 0.7686(3) 0.2821(2) 0.0577(8) Uani 1 1 d . . . C4 C 0.7528(6) 0.8805(3) 0.3116(3) 0.0721(11) Uani 1 1 d . . . H4 H 0.8723 0.9068 0.2977 0.087 Uiso 1 1 calc R . . C5 C 0.6694(7) 0.9523(3) 0.3621(3) 0.0780(12) Uani 1 1 d . . . H5 H 0.7334 1.0277 0.3829 0.094 Uiso 1 1 calc R . . C6 C 0.4938(7) 0.9132(3) 0.3815(3) 0.0706(11) Uani 1 1 d . . . H6 H 0.4359 0.9616 0.4147 0.085 Uiso 1 1 calc R . . C7 C 0.4025(5) 0.8010(3) 0.3515(2) 0.0561(8) Uani 1 1 d . . . C8 C 0.7236(6) 0.6824(3) 0.2283(2) 0.0632(9) Uani 1 1 d . . . H8 H 0.8407 0.6993 0.2099 0.076 Uiso 1 1 calc R . . N9 N 0.6167(4) 0.5831(3) 0.2073(2) 0.0596(7) Uani 1 1 d . . . O10 O 0.6904(5) 0.5071(3) 0.1565(3) 0.0929(11) Uani 1 1 d . . . H10 H 0.6041 0.4483 0.1350 0.111 Uiso 1 1 calc R . . C11 C 0.2154(5) 0.7485(3) 0.3696(2) 0.0590(8) Uani 1 1 d . . . H11 H 0.1463 0.7897 0.4025 0.071 Uiso 1 1 calc R . . N12 N 0.1533(4) 0.6441(2) 0.33813(18) 0.0556(7) Uani 1 1 d . . . O13 O -0.0210(5) 0.6001(3) 0.3581(2) 0.0802(9) Uani 1 1 d . . . H13 H -0.0590 0.5332 0.3331 0.096 Uiso 1 1 calc R . . N14 N 0.2230(4) 0.4140(2) 0.22128(17) 0.0488(6) Uani 1 1 d . . . C15 C 0.0991(5) 0.3670(3) 0.1481(2) 0.0551(8) Uani 1 1 d . . . C16 C 0.0089(6) 0.2541(3) 0.1165(3) 0.0690(10) Uani 1 1 d . . . H16 H -0.0789 0.2227 0.0665 0.083 Uiso 1 1 calc R . . C17 C 0.0529(7) 0.1890(3) 0.1616(3) 0.0706(10) Uani 1 1 d . . . H17 H -0.0033 0.1127 0.1412 0.085 Uiso 1 1 calc R . . C18 C 0.1787(6) 0.2373(3) 0.2355(3) 0.0651(9) Uani 1 1 d . . . H18 H 0.2096 0.1943 0.2658 0.078 Uiso 1 1 calc R . . C19 C 0.2598(5) 0.3508(3) 0.2650(2) 0.0522(7) Uani 1 1 d . . . C20 C 0.0668(6) 0.4429(3) 0.1055(2) 0.0598(8) Uani 1 1 d . . . H20 H -0.0168 0.4176 0.0547 0.072 Uiso 1 1 calc R . . N21 N 0.1564(5) 0.5442(2) 0.14025(18) 0.0572(7) Uani 1 1 d . . . O22 O 0.1171(6) 0.6092(2) 0.09500(19) 0.0819(9) Uani 1 1 d . . . H22 H 0.1446 0.6738 0.1254 0.098 Uiso 1 1 calc R . . C23 C 0.3927(5) 0.4097(3) 0.3442(2) 0.0554(8) Uani 1 1 d . . . H23 H 0.4178 0.3731 0.3805 0.066 Uiso 1 1 calc R . . N24 N 0.4728(4) 0.5122(2) 0.36188(18) 0.0550(7) Uani 1 1 d . . . O25 O 0.5965(5) 0.5607(2) 0.43720(18) 0.0747(8) Uani 1 1 d . . . H25 H 0.6466 0.6263 0.4446 0.090 Uiso 1 1 calc R . . Cl26 Cl 0.77467(15) 0.84751(8) 0.54628(6) 0.0652(3) Uani 1 1 d . . . O27 O 0.7899(6) 0.7790(3) 0.4676(2) 0.0896(10) Uani 1 1 d . . . O28 O 0.5786(6) 0.8203(4) 0.5545(3) 0.138(2) Uani 1 1 d . . . O29 O 0.8971(9) 0.8330(5) 0.6085(3) 0.148(2) Uani 1 1 d . . . O30 O 0.8324(5) 0.9603(3) 0.5520(2) 0.0900(10) Uani 1 1 d . . . Cl31A Cl 0.2358(10) 0.8918(5) 0.1446(4) 0.0476(16) Uiso 0.20 1 d PD A 1 O32A O 0.334(2) 0.8250(10) 0.1711(8) 0.064(3) Uiso 0.20 1 d PD A 1 O33A O 0.362(2) 0.9923(11) 0.1594(12) 0.091(5) Uiso 0.20 1 d PD A 1 O34A O 0.083(3) 0.903(3) 0.1957(16) 0.191(15) Uiso 0.20 1 d PD A 1 O35A O 0.139(3) 0.8336(14) 0.0662(8) 0.074(4) Uiso 0.20 1 d PD A 1 Cl31B Cl 0.2285(7) 0.9011(3) 0.1633(3) 0.0599(13) Uiso 0.40 1 d PD B 2 O32B O 0.1550(14) 0.8176(6) 0.1996(5) 0.076(2) Uiso 0.40 1 d PD B 2 O33B O 0.4204(15) 0.9457(11) 0.1731(8) 0.135(4) Uiso 0.40 1 d PD B 2 O34B O 0.158(2) 0.9907(11) 0.2126(9) 0.163(5) Uiso 0.40 1 d PD B 2 O35B O 0.107(2) 0.8708(14) 0.0853(8) 0.170(7) Uiso 0.40 1 d PD B 2 Cl31C Cl 0.1766(5) 0.8970(2) 0.1561(2) 0.0524(8) Uiso 0.40 1 d PD C 3 O32C O 0.2345(16) 0.8213(7) 0.1953(5) 0.076(2) Uiso 0.40 1 d PD C 3 O33C O 0.3325(16) 1.0015(8) 0.2010(7) 0.114(3) Uiso 0.40 1 d PD C 3 O34C O 0.0141(16) 0.9216(12) 0.1617(9) 0.140(4) Uiso 0.40 1 d PD C 3 O35C O 0.221(2) 0.8533(11) 0.0754(7) 0.128(5) Uiso 0.40 1 d PD C 3 O36 O -0.1586(5) 0.3812(3) 0.2922(2) 0.0898(10) Uani 1 1 d . . . C37 C -0.2007(6) 0.3192(4) 0.3310(3) 0.0707(10) Uani 1 1 d . . . C38 C -0.3190(7) 0.2020(4) 0.2863(3) 0.0873(14) Uani 1 1 d . . . H38A H -0.4169 0.1809 0.3167 0.105 Uiso 1 1 calc R . . H38B H -0.2348 0.1545 0.2810 0.105 Uiso 1 1 calc R . . H38C H -0.3813 0.1954 0.2326 0.105 Uiso 1 1 calc R . . C39 C -0.1470(9) 0.3550(5) 0.4220(4) 0.1089(18) Uani 1 1 d . . . H39A H -0.0407 0.3277 0.4368 0.131 Uiso 1 1 calc R . . H39B H -0.2579 0.3262 0.4436 0.131 Uiso 1 1 calc R . . H39C H -0.1077 0.4345 0.4446 0.131 Uiso 1 1 calc R . . O40 O 0.4963(6) 0.2931(3) 0.1033(2) 0.0930(10) Uani 1 1 d . . . C41 C 0.4285(7) 0.2392(4) 0.0324(3) 0.0820(12) Uani 1 1 d . . . C42 C 0.4014(11) 0.2925(6) -0.0298(4) 0.120(2) Uani 1 1 d . . . H42A H 0.5039 0.2897 -0.0613 0.144 Uiso 1 1 calc R . . H42B H 0.4060 0.3684 -0.0027 0.144 Uiso 1 1 calc R . . H42C H 0.2769 0.2542 -0.0659 0.144 Uiso 1 1 calc R . . C43 C 0.3582(10) 0.1152(5) 0.0054(4) 0.115(2) Uani 1 1 d . . . H43A H 0.3778 0.0919 0.0522 0.138 Uiso 1 1 calc R . . H43B H 0.4306 0.0838 -0.0345 0.138 Uiso 1 1 calc R . . H43C H 0.2215 0.0905 -0.0187 0.138 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 0.0543(3) 0.0401(3) 0.0514(3) 0.01733(18) 0.01028(18) 0.01280(17) N2 0.0565(15) 0.0430(14) 0.0534(15) 0.0209(12) 0.0050(12) 0.0129(11) C3 0.0578(19) 0.0544(19) 0.062(2) 0.0307(16) 0.0048(15) 0.0060(15) C4 0.070(2) 0.058(2) 0.081(3) 0.033(2) 0.0000(19) 0.0008(18) C5 0.097(3) 0.046(2) 0.079(3) 0.025(2) -0.005(2) 0.001(2) C6 0.091(3) 0.0425(18) 0.071(2) 0.0148(17) 0.003(2) 0.0169(18) C7 0.069(2) 0.0453(17) 0.0520(18) 0.0161(14) 0.0009(15) 0.0170(15) C8 0.0554(19) 0.065(2) 0.071(2) 0.0303(19) 0.0165(16) 0.0089(16) N9 0.0568(16) 0.0581(18) 0.0671(18) 0.0245(15) 0.0153(14) 0.0165(14) O10 0.087(2) 0.0683(19) 0.120(3) 0.0171(19) 0.050(2) 0.0228(16) C11 0.065(2) 0.0486(18) 0.062(2) 0.0120(16) 0.0115(16) 0.0213(15) N12 0.0618(17) 0.0491(15) 0.0570(16) 0.0161(13) 0.0141(13) 0.0191(13) O13 0.0778(19) 0.0623(17) 0.096(2) 0.0183(16) 0.0349(17) 0.0149(14) N14 0.0531(15) 0.0422(13) 0.0537(15) 0.0180(12) 0.0128(12) 0.0147(11) C15 0.064(2) 0.0452(17) 0.0556(19) 0.0165(15) 0.0116(15) 0.0142(14) C16 0.081(3) 0.0498(19) 0.062(2) 0.0082(17) 0.0059(18) 0.0087(18) C17 0.087(3) 0.0394(17) 0.080(3) 0.0190(18) 0.016(2) 0.0091(17) C18 0.074(2) 0.0475(18) 0.081(3) 0.0296(18) 0.0198(19) 0.0177(16) C19 0.0571(18) 0.0436(16) 0.0628(19) 0.0232(15) 0.0167(15) 0.0181(13) C20 0.069(2) 0.0519(19) 0.0512(18) 0.0142(15) -0.0008(15) 0.0137(16) N21 0.0686(18) 0.0508(16) 0.0533(16) 0.0214(13) 0.0065(13) 0.0164(13) O22 0.119(3) 0.0552(16) 0.0705(18) 0.0296(14) -0.0027(16) 0.0208(16) C23 0.065(2) 0.0506(18) 0.062(2) 0.0303(16) 0.0142(15) 0.0219(15) N24 0.0594(16) 0.0510(16) 0.0584(17) 0.0242(13) 0.0120(13) 0.0152(13) O25 0.0855(19) 0.0618(16) 0.0642(16) 0.0243(14) -0.0041(13) 0.0018(14) Cl26 0.0810(6) 0.0577(5) 0.0596(5) 0.0231(4) 0.0163(4) 0.0193(4) O27 0.131(3) 0.0656(18) 0.0749(19) 0.0221(15) 0.0358(19) 0.0274(18) O28 0.110(3) 0.096(3) 0.181(5) 0.015(3) 0.078(3) -0.003(2) O29 0.223(6) 0.154(4) 0.092(3) 0.056(3) 0.001(3) 0.093(4) O30 0.105(2) 0.0556(16) 0.099(2) 0.0218(16) 0.0173(18) 0.0097(15) O36 0.096(2) 0.0630(18) 0.108(3) 0.0268(18) 0.0375(19) 0.0142(16) C37 0.061(2) 0.061(2) 0.092(3) 0.026(2) 0.022(2) 0.0184(18) C38 0.084(3) 0.068(3) 0.106(4) 0.036(3) 0.022(3) 0.004(2) C39 0.118(5) 0.095(4) 0.098(4) 0.023(3) -0.006(3) 0.026(3) O40 0.106(2) 0.077(2) 0.089(2) 0.0208(19) 0.0165(19) 0.0232(18) C41 0.082(3) 0.077(3) 0.092(3) 0.028(3) 0.029(3) 0.025(2) C42 0.136(5) 0.124(5) 0.113(5) 0.056(4) 0.027(4) 0.036(4) C43 0.134(5) 0.079(3) 0.121(5) 0.014(3) 0.031(4) 0.033(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 N2 1.933(3) . ? Cu1 N14 1.958(3) . ? Cu1 N12 2.205(3) . ? Cu1 N9 2.211(3) . ? Cu1 N24 2.285(3) . ? Cu1 N21 2.295(3) . ? N2 C7 1.334(5) . ? N2 C3 1.351(5) . ? C3 C4 1.383(5) . ? C3 C8 1.455(6) . ? C4 C5 1.376(7) . ? C5 C6 1.360(6) . ? C6 C7 1.378(5) . ? C7 C11 1.468(5) . ? C8 N9 1.271(5) . ? N9 O10 1.370(4) . ? C11 N12 1.265(5) . ? N12 O13 1.372(4) . ? N14 C19 1.339(4) . ? N14 C15 1.346(5) . ? C15 C16 1.384(5) . ? C15 C20 1.460(5) . ? C16 C17 1.392(6) . ? C17 C18 1.362(6) . ? C18 C19 1.382(5) . ? C19 C23 1.459(5) . ? C20 N21 1.260(5) . ? N21 O22 1.383(4) . ? C23 N24 1.266(4) . ? N24 O25 1.373(4) . ? Cl26 O28 1.398(4) . ? Cl26 O29 1.407(4) . ? Cl26 O30 1.418(3) . ? Cl26 O27 1.422(3) . ? Cl31A O33A 1.351(12) . ? Cl31A O35A 1.356(12) . ? Cl31A O32A 1.398(12) . ? Cl31A O34A 1.484(15) . ? Cl31B O33B 1.331(11) . ? Cl31B O35B 1.418(12) . ? Cl31B O32B 1.451(8) . ? Cl31B O34B 1.465(12) . ? Cl31C O34C 1.285(10) . ? Cl31C O35C 1.446(11) . ? Cl31C O32C 1.479(8) . ? Cl31C O33C 1.482(9) . ? O36 C37 1.215(6) . ? C37 C39 1.485(7) . ? C37 C38 1.493(6) . ? O40 C41 1.199(6) . ? C41 C42 1.478(8) . ? C41 C43 1.501(7) . ? 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 N2 Cu1 N14 178.85(11) . . ? N2 Cu1 N12 77.07(12) . . ? N14 Cu1 N12 104.06(11) . . ? N2 Cu1 N9 77.14(12) . . ? N14 Cu1 N9 101.73(11) . . ? N12 Cu1 N9 154.21(12) . . ? N2 Cu1 N24 104.11(11) . . ? N14 Cu1 N24 76.12(11) . . ? N12 Cu1 N24 92.77(11) . . ? N9 Cu1 N24 93.78(11) . . ? N2 Cu1 N21 104.07(11) . . ? N14 Cu1 N21 75.69(11) . . ? N12 Cu1 N21 93.89(11) . . ? N9 Cu1 N21 92.02(12) . . ? N24 Cu1 N21 151.81(11) . . ? C7 N2 C3 120.3(3) . . ? C7 N2 Cu1 119.8(2) . . ? C3 N2 Cu1 119.8(2) . . ? N2 C3 C4 120.4(4) . . ? N2 C3 C8 114.1(3) . . ? C4 C3 C8 125.5(4) . . ? C5 C4 C3 118.8(4) . . ? C6 C5 C4 120.2(4) . . ? C5 C6 C7 119.3(4) . . ? N2 C7 C6 121.0(4) . . ? N2 C7 C11 114.6(3) . . ? C6 C7 C11 124.4(3) . . ? N9 C8 C3 117.4(3) . . ? C8 N9 O10 113.9(3) . . ? C8 N9 Cu1 111.5(3) . . ? O10 N9 Cu1 134.6(2) . . ? N12 C11 C7 116.4(3) . . ? C11 N12 O13 113.5(3) . . ? C11 N12 Cu1 112.1(2) . . ? O13 N12 Cu1 134.3(2) . . ? C19 N14 C15 119.6(3) . . ? C19 N14 Cu1 120.1(2) . . ? C15 N14 Cu1 120.3(2) . . ? N14 C15 C16 121.5(3) . . ? N14 C15 C20 115.5(3) . . ? C16 C15 C20 123.0(3) . . ? C15 C16 C17 118.2(4) . . ? C18 C17 C16 119.8(3) . . ? C17 C18 C19 119.3(4) . . ? N14 C19 C18 121.5(3) . . ? N14 C19 C23 115.5(3) . . ? C18 C19 C23 123.0(3) . . ? N21 C20 C15 117.5(3) . . ? C20 N21 O22 113.2(3) . . ? C20 N21 Cu1 111.0(2) . . ? O22 N21 Cu1 135.9(2) . . ? N24 C23 C19 117.8(3) . . ? C23 N24 O25 113.8(3) . . ? C23 N24 Cu1 110.3(2) . . ? O25 N24 Cu1 135.6(2) . . ? O28 Cl26 O29 111.6(4) . . ? O28 Cl26 O30 108.1(3) . . ? O29 Cl26 O30 108.8(3) . . ? O28 Cl26 O27 108.3(3) . . ? O29 Cl26 O27 109.9(3) . . ? O30 Cl26 O27 110.0(2) . . ? O33A Cl31A O35A 118.0(11) . . ? O33A Cl31A O32A 109.5(10) . . ? O35A Cl31A O32A 107.6(9) . . ? O33A Cl31A O34A 109.9(12) . . ? O35A Cl31A O34A 106.1(12) . . ? O32A Cl31A O34A 104.9(12) . . ? O33B Cl31B O35B 119.7(9) . . ? O33B Cl31B O32B 120.2(8) . . ? O35B Cl31B O32B 107.7(8) . . ? O33B Cl31B O34B 104.7(8) . . ? O35B Cl31B O34B 101.1(9) . . ? O32B Cl31B O34B 99.4(7) . . ? O34C Cl31C O35C 118.9(8) . . ? O34C Cl31C O32C 122.0(8) . . ? O35C Cl31C O32C 100.2(6) . . ? O34C Cl31C O33C 105.7(8) . . ? O35C Cl31C O33C 106.9(7) . . ? O32C Cl31C O33C 101.1(6) . . ? O36 C37 C39 123.2(4) . . ? O36 C37 C38 119.2(4) . . ? C39 C37 C38 117.5(4) . . ? O40 C41 C42 121.3(5) . . ? O40 C41 C43 120.5(5) . . ? C42 C41 C43 118.1(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O10 H10 O40 0.82 1.89 2.658(5) 154.9 . O13 H13 O36 0.82 1.84 2.657(5) 170.8 . O22 H22 O32A 0.82 2.00 2.734(13) 149.4 . O22 H22 O32B 0.82 1.92 2.732(9) 168.4 . O22 H22 O32C 0.82 1.87 2.685(9) 174.0 . O22 H22 O35A 0.82 2.62 3.125(18) 121.2 . O22 H22 O35B 0.82 2.95 3.528(18) 129.1 . O22 H22 O35C 0.82 2.72 3.265(14) 125.2 . O25 H25 O27 0.82 1.93 2.747(4) 173.9 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.688 _refine_diff_density_min -0.912 _refine_diff_density_rms 0.133 #=END data_mh68 _database_code_depnum_ccdc_archive 'CCDC 217088' _chemical_name_common ;Bis(2,6-bis(oximomethyl)pyridine)copper(ii) diperchlorate bis- acetone solvate ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis[2,6-bis{oximomethyl}pyridine]copper(II) diperchlorate bis-acetone solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Cu N6 O4, 2[Cl O4], 2[C3 H6 O]' _chemical_formula_sum 'C20 H26 Cl2 Cu N6 O14' _chemical_formula_weight 708.91 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9012(2) _cell_length_b 13.1087(3) _cell_length_c 17.5759(4) _cell_angle_alpha 107.2644(16) _cell_angle_beta 94.6164(16) _cell_angle_gamma 105.2984(10) _cell_volume 1442.66(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25848 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 27.49 _exptl_crystal_description Prism _exptl_crystal_colour Green _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 726 _exptl_absorpt_coefficient_mu 1.020 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.799 _exptl_absorpt_correction_T_max 0.854 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV. See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD diffractometer' _diffrn_measurement_method 'Area detector scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25848 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6541 _reflns_number_gt 5587 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _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. There is no disorder in this structure. All non-H atoms were refined anisotropically. All C-bound H atoms were placed in calculated positions, and refined using a riding model. All O-H H atoms were located in the difference map, then allowed to refine with a common thermal parameter subject to the restraints O-H = 0.79(2)\%A. ; _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^)+(0.0477P)^2^+0.6784P] 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 SHELXL _refine_ls_extinction_coef 0.0103(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6541 _refine_ls_number_parameters 407 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.35657(4) 0.579284(19) 0.260728(14) 0.02959(10) Uani 1 1 d . . . N2 N 0.5058(3) 0.73640(14) 0.29756(10) 0.0303(3) Uani 1 1 d . . . C3 C 0.6859(3) 0.77126(18) 0.27412(13) 0.0338(4) Uani 1 1 d . . . C4 C 0.8006(3) 0.88336(19) 0.30125(14) 0.0399(5) Uani 1 1 d . . . H4 H 0.9279 0.9072 0.2848 0.048 Uiso 1 1 calc R . . C5 C 0.7241(4) 0.95984(19) 0.35323(14) 0.0403(5) Uani 1 1 d . . . H5 H 0.8000 1.0371 0.3730 0.048 Uiso 1 1 calc R . . C6 C 0.5379(3) 0.92388(18) 0.37623(13) 0.0372(5) Uani 1 1 d . . . H6 H 0.4841 0.9760 0.4111 0.045 Uiso 1 1 calc R . . C7 C 0.4315(3) 0.81075(17) 0.34752(12) 0.0325(4) Uani 1 1 d . . . C8 C 0.7429(3) 0.68042(19) 0.21914(13) 0.0370(5) Uani 1 1 d . . . H8 H 0.8656 0.6940 0.1977 0.044 Uiso 1 1 calc R . . N9 N 0.6190(3) 0.58146(15) 0.20134(11) 0.0353(4) Uani 1 1 d . . . O10 O 0.6796(3) 0.50088(15) 0.14720(12) 0.0507(4) Uani 1 1 d D . . H10 H 0.602(4) 0.442(2) 0.1438(18) 0.056(4) Uiso 1 1 d D . . C11 C 0.2349(3) 0.75942(17) 0.36723(13) 0.0345(4) Uani 1 1 d . . . H11 H 0.1657 0.8027 0.4017 0.041 Uiso 1 1 calc R . . N12 N 0.1616(3) 0.65277(14) 0.33533(11) 0.0327(4) Uani 1 1 d . . . O13 O -0.0210(3) 0.60978(14) 0.35703(11) 0.0433(4) Uani 1 1 d D . . H13 H -0.053(4) 0.5452(19) 0.3345(18) 0.056(4) Uiso 1 1 d D . . N14 N 0.2099(3) 0.41795(14) 0.22197(10) 0.0290(3) Uani 1 1 d . . . C15 C 0.0796(3) 0.37013(17) 0.15053(12) 0.0312(4) Uani 1 1 d . . . C16 C -0.0263(3) 0.25679(18) 0.12185(13) 0.0360(5) Uani 1 1 d . . . H16 H -0.1201 0.2253 0.0723 0.043 Uiso 1 1 calc R . . C17 C 0.0068(4) 0.19020(18) 0.16661(13) 0.0378(5) Uani 1 1 d . . . H17 H -0.0621 0.1120 0.1475 0.045 Uiso 1 1 calc R . . C18 C 0.1415(3) 0.23850(18) 0.23958(13) 0.0354(4) Uani 1 1 d . . . H18 H 0.1667 0.1938 0.2708 0.043 Uiso 1 1 calc R . . C19 C 0.2389(3) 0.35319(17) 0.26632(12) 0.0304(4) Uani 1 1 d . . . C20 C 0.0574(3) 0.44517(18) 0.10548(13) 0.0344(4) Uani 1 1 d . . . H20 H -0.0272 0.4177 0.0539 0.041 Uiso 1 1 calc R . . N21 N 0.1559(3) 0.54860(15) 0.13806(10) 0.0334(4) Uani 1 1 d . . . O22 O 0.1255(3) 0.61195(14) 0.09003(10) 0.0436(4) Uani 1 1 d D . . H22 H 0.177(4) 0.6744(19) 0.1202(17) 0.056(4) Uiso 1 1 d D . . C23 C 0.3781(3) 0.41101(17) 0.34373(12) 0.0324(4) Uani 1 1 d . . . H23 H 0.3980 0.3725 0.3804 0.039 Uiso 1 1 calc R . . N24 N 0.4720(3) 0.51498(14) 0.36028(10) 0.0322(4) Uani 1 1 d . . . O25 O 0.6019(2) 0.56132(14) 0.43350(9) 0.0395(4) Uani 1 1 d D . . H25 H 0.653(4) 0.6254(19) 0.4370(18) 0.056(4) Uiso 1 1 d D . . Cl26 Cl 0.73937(8) 0.84865(4) 0.53674(3) 0.03475(13) Uani 1 1 d . . . O27 O 0.7936(3) 0.78545(13) 0.46289(9) 0.0419(4) Uani 1 1 d . . . O28 O 0.5204(3) 0.81514(15) 0.52971(11) 0.0495(4) Uani 1 1 d . . . O29 O 0.8281(3) 0.82403(16) 0.60369(10) 0.0544(5) Uani 1 1 d . . . O30 O 0.8153(2) 0.96564(13) 0.54870(10) 0.0425(4) Uani 1 1 d . . . Cl31 Cl 0.26723(9) 0.90437(4) 0.15107(3) 0.04068(14) Uani 1 1 d . . . O32 O 0.2321(3) 0.82381(14) 0.19387(10) 0.0555(5) Uani 1 1 d . . . O33 O 0.4789(3) 0.96191(19) 0.16475(14) 0.0756(6) Uani 1 1 d . . . O34 O 0.1592(4) 0.9810(2) 0.18014(17) 0.0884(8) Uani 1 1 d . . . O35 O 0.1995(4) 0.84367(18) 0.06648(11) 0.0683(6) Uani 1 1 d . . . O36 O -0.1861(3) 0.39052(13) 0.29241(10) 0.0434(4) Uani 1 1 d . . . C37 C -0.2178(3) 0.32495(19) 0.33042(15) 0.0398(5) Uani 1 1 d . . . C38 C -0.3566(4) 0.20811(19) 0.29091(16) 0.0466(6) Uani 1 1 d . . . H38A H -0.4611 0.1922 0.3239 0.056 Uiso 1 1 calc R . . H38B H -0.2774 0.1551 0.2858 0.056 Uiso 1 1 calc R . . H38C H -0.4222 0.2004 0.2371 0.056 Uiso 1 1 calc R . . C39 C -0.1225(4) 0.3577(2) 0.41679(17) 0.0545(6) Uani 1 1 d . . . H39A H -0.0503 0.3047 0.4228 0.065 Uiso 1 1 calc R . . H39B H -0.2289 0.3566 0.4506 0.065 Uiso 1 1 calc R . . H39C H -0.0259 0.4334 0.4337 0.065 Uiso 1 1 calc R . . O40 O 0.4688(3) 0.28538(14) 0.10373(10) 0.0476(4) Uani 1 1 d . . . C41 C 0.3874(4) 0.2289(2) 0.03445(15) 0.0421(5) Uani 1 1 d . . . C42 C 0.3647(5) 0.2800(3) -0.03051(18) 0.0605(7) Uani 1 1 d . . . H42A H 0.4150 0.2413 -0.0779 0.073 Uiso 1 1 calc R . . H42B H 0.4438 0.3596 -0.0103 0.073 Uiso 1 1 calc R . . H42C H 0.2205 0.2724 -0.0457 0.073 Uiso 1 1 calc R . . C43 C 0.3022(5) 0.1042(2) 0.00991(18) 0.0580(7) Uani 1 1 d . . . H43A H 0.1573 0.0811 -0.0134 0.070 Uiso 1 1 calc R . . H43B H 0.3176 0.0807 0.0574 0.070 Uiso 1 1 calc R . . H43C H 0.3759 0.0691 -0.0304 0.070 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 0.03168(15) 0.02816(14) 0.03021(15) 0.01000(10) 0.00606(10) 0.01052(10) N2 0.0318(9) 0.0330(9) 0.0285(8) 0.0122(7) 0.0030(7) 0.0120(7) C3 0.0340(11) 0.0369(11) 0.0336(11) 0.0163(9) 0.0029(8) 0.0113(9) C4 0.0365(11) 0.0401(12) 0.0428(12) 0.0195(10) 0.0027(9) 0.0059(9) C5 0.0427(12) 0.0312(11) 0.0433(12) 0.0154(9) -0.0039(10) 0.0053(9) C6 0.0435(12) 0.0317(11) 0.0357(11) 0.0103(9) -0.0002(9) 0.0133(9) C7 0.0370(11) 0.0329(10) 0.0297(10) 0.0116(8) 0.0021(8) 0.0137(9) C8 0.0314(10) 0.0430(12) 0.0398(12) 0.0172(10) 0.0081(9) 0.0119(9) N9 0.0344(9) 0.0367(10) 0.0368(10) 0.0121(8) 0.0082(7) 0.0137(8) O10 0.0483(10) 0.0411(9) 0.0609(11) 0.0085(9) 0.0243(9) 0.0159(8) C11 0.0390(11) 0.0328(10) 0.0328(11) 0.0083(8) 0.0053(9) 0.0162(9) N12 0.0330(9) 0.0321(9) 0.0348(9) 0.0117(7) 0.0070(7) 0.0118(7) O13 0.0393(9) 0.0344(8) 0.0535(10) 0.0099(8) 0.0172(7) 0.0093(7) N14 0.0316(8) 0.0316(8) 0.0273(8) 0.0107(7) 0.0070(7) 0.0138(7) C15 0.0345(10) 0.0324(10) 0.0292(10) 0.0098(8) 0.0073(8) 0.0140(8) C16 0.0393(11) 0.0351(11) 0.0297(10) 0.0056(8) 0.0019(8) 0.0116(9) C17 0.0444(12) 0.0283(10) 0.0373(12) 0.0078(9) 0.0064(9) 0.0092(9) C18 0.0422(12) 0.0324(10) 0.0349(11) 0.0127(9) 0.0085(9) 0.0141(9) C19 0.0327(10) 0.0309(10) 0.0306(10) 0.0112(8) 0.0078(8) 0.0128(8) C20 0.0384(11) 0.0361(11) 0.0301(10) 0.0108(9) 0.0033(8) 0.0144(9) N21 0.0373(9) 0.0354(9) 0.0321(9) 0.0150(7) 0.0055(7) 0.0145(8) O22 0.0593(11) 0.0353(8) 0.0389(9) 0.0182(7) 0.0018(8) 0.0137(8) C23 0.0363(11) 0.0335(10) 0.0320(10) 0.0144(8) 0.0066(8) 0.0139(9) N24 0.0339(9) 0.0335(9) 0.0289(9) 0.0093(7) 0.0034(7) 0.0113(7) O25 0.0406(9) 0.0368(8) 0.0354(8) 0.0116(7) -0.0027(6) 0.0053(7) Cl26 0.0387(3) 0.0343(3) 0.0312(3) 0.0115(2) 0.0064(2) 0.0101(2) O27 0.0516(10) 0.0365(8) 0.0372(8) 0.0089(7) 0.0142(7) 0.0146(7) O28 0.0380(9) 0.0524(10) 0.0508(10) 0.0126(8) 0.0113(7) 0.0058(8) O29 0.0696(12) 0.0618(11) 0.0396(9) 0.0274(9) 0.0039(8) 0.0225(10) O30 0.0463(9) 0.0312(8) 0.0470(9) 0.0108(7) 0.0084(7) 0.0093(7) Cl31 0.0546(3) 0.0341(3) 0.0359(3) 0.0135(2) 0.0058(2) 0.0158(2) O32 0.0888(14) 0.0380(9) 0.0401(10) 0.0173(8) 0.0011(9) 0.0176(9) O33 0.0617(13) 0.0644(13) 0.0735(15) 0.0051(11) 0.0073(11) -0.0039(11) O34 0.119(2) 0.0795(16) 0.114(2) 0.0537(15) 0.0577(17) 0.0712(16) O35 0.0926(16) 0.0625(12) 0.0354(10) 0.0174(9) -0.0076(10) 0.0036(11) O36 0.0446(9) 0.0350(8) 0.0516(10) 0.0134(7) 0.0162(7) 0.0124(7) C37 0.0367(12) 0.0365(11) 0.0481(13) 0.0114(10) 0.0139(10) 0.0152(9) C38 0.0504(14) 0.0354(12) 0.0513(14) 0.0124(11) 0.0129(11) 0.0098(10) C39 0.0513(15) 0.0524(15) 0.0550(16) 0.0151(13) 0.0041(12) 0.0123(12) O40 0.0530(10) 0.0417(9) 0.0456(10) 0.0101(8) 0.0086(8) 0.0152(8) C41 0.0413(12) 0.0422(12) 0.0471(14) 0.0154(11) 0.0141(10) 0.0170(10) C42 0.0700(19) 0.0647(18) 0.0569(17) 0.0293(14) 0.0144(14) 0.0253(15) C43 0.0690(18) 0.0422(14) 0.0571(17) 0.0102(12) 0.0188(14) 0.0124(13) _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 N2 1.9246(17) . ? Cu1 N14 1.9661(17) . ? Cu1 N9 2.1601(18) . ? Cu1 N12 2.1624(17) . ? Cu1 N24 2.3265(17) . ? Cu1 N21 2.3322(17) . ? N2 C7 1.346(3) . ? N2 C3 1.348(3) . ? C3 C4 1.387(3) . ? C3 C8 1.460(3) . ? C4 C5 1.390(3) . ? C5 C6 1.383(3) . ? C6 C7 1.384(3) . ? C7 C11 1.465(3) . ? C8 N9 1.282(3) . ? N9 O10 1.377(2) . ? O10 H10 0.79(2) . ? C11 N12 1.281(3) . ? N12 O13 1.372(2) . ? O13 H13 0.78(2) . ? N14 C19 1.351(3) . ? N14 C15 1.353(3) . ? C15 C16 1.385(3) . ? C15 C20 1.463(3) . ? C16 C17 1.385(3) . ? C17 C18 1.387(3) . ? C18 C19 1.389(3) . ? C19 C23 1.463(3) . ? C20 N21 1.272(3) . ? N21 O22 1.388(2) . ? O22 H22 0.80(2) . ? C23 N24 1.277(3) . ? N24 O25 1.375(2) . ? O25 H25 0.80(2) . ? Cl26 O30 1.4274(16) . ? Cl26 O29 1.4414(17) . ? Cl26 O28 1.4423(17) . ? Cl26 O27 1.4541(16) . ? Cl31 O34 1.407(2) . ? Cl31 O33 1.420(2) . ? Cl31 O35 1.4325(19) . ? Cl31 O32 1.4511(17) . ? O36 C37 1.224(3) . ? C37 C39 1.491(4) . ? C37 C38 1.494(3) . ? O40 C41 1.217(3) . ? C41 C43 1.496(3) . ? C41 C42 1.502(4) . ? 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 N2 Cu1 N14 178.59(7) . . ? N2 Cu1 N9 77.76(7) . . ? N14 Cu1 N9 100.86(7) . . ? N2 Cu1 N12 77.64(7) . . ? N14 Cu1 N12 103.76(7) . . ? N9 Cu1 N12 155.36(7) . . ? N2 Cu1 N24 103.97(7) . . ? N14 Cu1 N24 75.86(6) . . ? N9 Cu1 N24 95.42(6) . . ? N12 Cu1 N24 91.81(6) . . ? N2 Cu1 N21 104.75(6) . . ? N14 Cu1 N21 75.41(6) . . ? N9 Cu1 N21 89.73(7) . . ? N12 Cu1 N21 95.18(6) . . ? N24 Cu1 N21 151.27(6) . . ? C7 N2 C3 120.33(19) . . ? C7 N2 Cu1 119.89(14) . . ? C3 N2 Cu1 119.78(14) . . ? N2 C3 C4 121.5(2) . . ? N2 C3 C8 113.39(19) . . ? C4 C3 C8 125.2(2) . . ? C3 C4 C5 118.1(2) . . ? C6 C5 C4 120.2(2) . . ? C7 C6 C5 118.9(2) . . ? N2 C7 C6 121.0(2) . . ? N2 C7 C11 113.54(18) . . ? C6 C7 C11 125.45(19) . . ? N9 C8 C3 116.58(19) . . ? C8 N9 O10 113.24(18) . . ? C8 N9 Cu1 112.47(14) . . ? O10 N9 Cu1 134.26(14) . . ? H10 O10 N9 106(2) . . ? N12 C11 C7 116.15(18) . . ? C11 N12 O13 113.28(17) . . ? C11 N12 Cu1 112.78(14) . . ? O13 N12 Cu1 133.93(13) . . ? H13 O13 N12 105(2) . . ? C19 N14 C15 119.11(18) . . ? C19 N14 Cu1 120.26(14) . . ? C15 N14 Cu1 120.63(13) . . ? N14 C15 C16 121.88(18) . . ? N14 C15 C20 116.06(18) . . ? C16 C15 C20 122.05(19) . . ? C17 C16 C15 118.9(2) . . ? C16 C17 C18 119.5(2) . . ? C17 C18 C19 118.97(19) . . ? N14 C19 C18 121.59(19) . . ? N14 C19 C23 116.10(18) . . ? C18 C19 C23 122.31(18) . . ? N21 C20 C15 117.40(19) . . ? C20 N21 O22 112.68(17) . . ? C20 N21 Cu1 110.44(13) . . ? O22 N21 Cu1 136.76(13) . . ? H22 O22 N21 102(2) . . ? N24 C23 C19 117.65(18) . . ? C23 N24 O25 113.34(17) . . ? C23 N24 Cu1 109.90(13) . . ? O25 N24 Cu1 136.56(13) . . ? H25 O25 N24 105(2) . . ? O30 Cl26 O29 110.04(11) . . ? O30 Cl26 O28 110.03(10) . . ? O29 Cl26 O28 109.56(11) . . ? O30 Cl26 O27 109.52(10) . . ? O29 Cl26 O27 108.70(11) . . ? O28 Cl26 O27 108.97(10) . . ? O34 Cl31 O33 109.88(16) . . ? O34 Cl31 O35 111.82(16) . . ? O33 Cl31 O35 109.16(14) . . ? O34 Cl31 O32 108.54(13) . . ? O33 Cl31 O32 109.60(14) . . ? O35 Cl31 O32 107.79(11) . . ? O36 C37 C39 122.0(2) . . ? O36 C37 C38 120.3(2) . . ? C39 C37 C38 117.7(2) . . ? O40 C41 C43 121.3(2) . . ? O40 C41 C42 122.3(2) . . ? C43 C41 C42 116.5(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O10 H10 O40 0.79(2) 1.90(2) 2.655(3) 159(3) . O13 H13 O36 0.78(2) 1.88(2) 2.641(2) 166(3) . O22 H22 O32 0.80(2) 1.92(2) 2.699(2) 166(3) . O22 H22 O35 0.80(2) 2.63(3) 3.102(3) 119(3) . O25 H25 O27 0.80(2) 1.96(2) 2.754(2) 171(3) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.442 _refine_diff_density_min -0.638 _refine_diff_density_rms 0.064 #=END data_mh68100 _database_code_depnum_ccdc_archive 'CCDC 217089' _chemical_name_common ;Bis(2,6-bis(oximomethyl)pyridine)copper(ii) diperchlorate bis- acetone solvate ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis[2,6-bis{oximomethyl}pyridine]copper(II) diperchlorate bis-acetone solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Cu N6 O4, 2[Cl O4], 2[C3 H6 O]' _chemical_formula_sum 'C20 H26 Cl2 Cu N6 O14' _chemical_formula_weight 708.91 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8580(2) _cell_length_b 13.0630(3) _cell_length_c 17.5689(5) _cell_angle_alpha 107.2649(14) _cell_angle_beta 94.1119(11) _cell_angle_gamma 105.6603(10) _cell_volume 1427.36(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 24468 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 27.53 _exptl_crystal_description Prism _exptl_crystal_colour Green _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 726 _exptl_absorpt_coefficient_mu 1.031 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.654 _exptl_absorpt_correction_T_max 0.798 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV. See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_ambient_temperature 100(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 'Nonius KappaCCD diffractometer' _diffrn_measurement_method 'Area detector scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24468 _diffrn_reflns_av_R_equivalents 0.0851 _diffrn_reflns_av_sigmaI/netI 0.0578 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6413 _reflns_number_gt 5356 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _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. There is no disorder in this structure. All non-H atoms were refined anisotropically. All C-bound H atoms were placed in calculated positions, and refined using a riding model. All O-H H atoms were located in the difference map, then allowed to refine with a common thermal parameter subject to the restraints O-H = 0.77(2)\%A. ; _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^)+(0.0653P)^2^+0.2543P] 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 SHELXL _refine_ls_extinction_coef 0.0067(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6413 _refine_ls_number_parameters 407 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1140 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.35657(4) 0.580253(19) 0.260301(14) 0.02407(11) Uani 1 1 d . . . N2 N 0.5094(3) 0.73808(14) 0.29639(10) 0.0253(4) Uani 1 1 d . . . C3 C 0.6909(3) 0.77196(18) 0.27232(12) 0.0269(4) Uani 1 1 d . . . C4 C 0.8081(3) 0.88458(18) 0.29928(13) 0.0311(5) Uani 1 1 d . . . H4 H 0.9364 0.9081 0.2824 0.037 Uiso 1 1 calc R . . C5 C 0.7332(3) 0.96181(18) 0.35139(13) 0.0309(5) Uani 1 1 d . . . H5 H 0.8111 1.0392 0.3709 0.037 Uiso 1 1 calc R . . C6 C 0.5445(3) 0.92657(17) 0.37519(13) 0.0293(5) Uani 1 1 d . . . H6 H 0.4914 0.9792 0.4104 0.035 Uiso 1 1 calc R . . C7 C 0.4356(3) 0.81274(17) 0.34641(12) 0.0259(4) Uani 1 1 d . . . C8 C 0.7455(3) 0.68008(18) 0.21708(13) 0.0298(5) Uani 1 1 d . . . H8 H 0.8685 0.6930 0.1948 0.036 Uiso 1 1 calc R . . N9 N 0.6197(3) 0.58127(15) 0.20020(11) 0.0285(4) Uani 1 1 d . . . O10 O 0.6773(3) 0.50001(14) 0.14564(11) 0.0380(4) Uani 1 1 d D . . H10 H 0.598(4) 0.4421(18) 0.1378(16) 0.038(4) Uiso 1 1 d D . . C11 C 0.2370(3) 0.76184(17) 0.36671(12) 0.0277(4) Uani 1 1 d . . . H11 H 0.1682 0.8056 0.4015 0.033 Uiso 1 1 calc R . . N12 N 0.1615(3) 0.65459(14) 0.33468(11) 0.0265(4) Uani 1 1 d . . . O13 O -0.0223(2) 0.61143(13) 0.35672(10) 0.0338(4) Uani 1 1 d D . . H13 H -0.057(4) 0.5489(17) 0.3371(16) 0.038(4) Uiso 1 1 d D . . N14 N 0.2055(3) 0.41793(14) 0.22218(10) 0.0240(4) Uani 1 1 d . . . C15 C 0.0754(3) 0.37024(17) 0.15118(12) 0.0256(4) Uani 1 1 d . . . C16 C -0.0340(3) 0.25612(18) 0.12305(13) 0.0285(4) Uani 1 1 d . . . H16 H -0.1279 0.2244 0.0736 0.034 Uiso 1 1 calc R . . C17 C -0.0036(3) 0.18939(18) 0.16837(13) 0.0291(5) Uani 1 1 d . . . H17 H -0.0753 0.1110 0.1499 0.035 Uiso 1 1 calc R . . C18 C 0.1323(3) 0.23802(17) 0.24089(13) 0.0271(4) Uani 1 1 d . . . H18 H 0.1565 0.1932 0.2722 0.033 Uiso 1 1 calc R . . C19 C 0.2328(3) 0.35344(17) 0.26725(12) 0.0256(4) Uani 1 1 d . . . C20 C 0.0558(3) 0.44476(18) 0.10557(12) 0.0277(4) Uani 1 1 d . . . H20 H -0.0286 0.4169 0.0541 0.033 Uiso 1 1 calc R . . N21 N 0.1566(3) 0.54878(14) 0.13765(10) 0.0267(4) Uani 1 1 d . . . O22 O 0.1278(3) 0.61189(13) 0.08894(10) 0.0332(4) Uani 1 1 d D . . H22 H 0.179(4) 0.6744(18) 0.1180(15) 0.038(4) Uiso 1 1 d D . . C23 C 0.3726(3) 0.41152(17) 0.34425(13) 0.0266(4) Uani 1 1 d . . . H23 H 0.3906 0.3731 0.3811 0.032 Uiso 1 1 calc R . . N24 N 0.4699(3) 0.51575(14) 0.36029(10) 0.0260(4) Uani 1 1 d . . . O25 O 0.6000(2) 0.56200(13) 0.43307(9) 0.0309(3) Uani 1 1 d D . . H25 H 0.665(4) 0.6210(18) 0.4347(16) 0.038(4) Uiso 1 1 d D . . Cl26 Cl 0.73515(8) 0.84907(4) 0.53465(3) 0.02649(13) Uani 1 1 d . . . O27 O 0.7933(2) 0.78732(12) 0.46097(9) 0.0322(3) Uani 1 1 d . . . O28 O 0.5142(2) 0.81472(13) 0.52666(10) 0.0358(4) Uani 1 1 d . . . O29 O 0.8202(3) 0.82202(14) 0.60131(10) 0.0379(4) Uani 1 1 d . . . O30 O 0.8140(2) 0.96755(12) 0.54834(9) 0.0324(4) Uani 1 1 d . . . Cl31 Cl 0.27694(9) 0.90563(4) 0.14994(3) 0.03066(14) Uani 1 1 d . . . O32 O 0.2384(3) 0.82468(13) 0.19337(10) 0.0401(4) Uani 1 1 d . . . O33 O 0.4916(3) 0.96226(16) 0.16287(12) 0.0512(5) Uani 1 1 d . . . O34 O 0.1684(3) 0.98411(16) 0.17861(13) 0.0550(5) Uani 1 1 d . . . O35 O 0.2051(3) 0.84391(15) 0.06522(10) 0.0473(5) Uani 1 1 d . . . O36 O -0.1938(2) 0.39152(12) 0.29163(10) 0.0330(4) Uani 1 1 d . . . C37 C -0.2250(3) 0.32577(18) 0.33010(14) 0.0299(5) Uani 1 1 d . . . C38 C -0.3689(4) 0.20860(18) 0.29125(14) 0.0341(5) Uani 1 1 d . . . H38A H -0.4758 0.1944 0.3243 0.041 Uiso 1 1 calc R . . H38B H -0.2922 0.1543 0.2869 0.041 Uiso 1 1 calc R . . H38C H -0.4326 0.2006 0.2372 0.041 Uiso 1 1 calc R . . C39 C -0.1242(4) 0.3581(2) 0.41570(15) 0.0401(6) Uani 1 1 d . . . H39A H -0.0532 0.3039 0.4204 0.048 Uiso 1 1 calc R . . H39B H -0.2285 0.3580 0.4510 0.048 Uiso 1 1 calc R . . H39C H -0.0247 0.4335 0.4318 0.048 Uiso 1 1 calc R . . O40 O 0.4629(2) 0.28387(13) 0.10389(9) 0.0358(4) Uani 1 1 d . . . C41 C 0.3803(4) 0.22792(19) 0.03476(14) 0.0328(5) Uani 1 1 d . . . C42 C 0.3603(4) 0.2798(2) -0.02982(16) 0.0446(6) Uani 1 1 d . . . H42A H 0.4141 0.2422 -0.0768 0.053 Uiso 1 1 calc R . . H42B H 0.4385 0.3601 -0.0090 0.053 Uiso 1 1 calc R . . H42C H 0.2154 0.2712 -0.0458 0.053 Uiso 1 1 calc R . . C43 C 0.2903(4) 0.10230(19) 0.00999(16) 0.0420(6) Uani 1 1 d . . . H43A H 0.1473 0.0799 -0.0163 0.050 Uiso 1 1 calc R . . H43B H 0.2953 0.0787 0.0579 0.050 Uiso 1 1 calc R . . H43C H 0.3695 0.0663 -0.0278 0.050 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 0.02398(16) 0.02283(15) 0.02492(16) 0.00755(11) 0.00329(11) 0.00692(11) N2 0.0259(9) 0.0265(8) 0.0240(9) 0.0092(7) 0.0010(7) 0.0088(7) C3 0.0248(10) 0.0314(10) 0.0254(10) 0.0121(8) 0.0006(8) 0.0079(8) C4 0.0278(11) 0.0323(11) 0.0324(11) 0.0141(9) 0.0008(9) 0.0053(9) C5 0.0305(12) 0.0256(10) 0.0342(12) 0.0116(9) -0.0032(9) 0.0052(9) C6 0.0312(12) 0.0270(10) 0.0283(11) 0.0079(9) -0.0022(9) 0.0096(9) C7 0.0276(11) 0.0271(10) 0.0236(10) 0.0091(8) -0.0002(8) 0.0096(8) C8 0.0269(11) 0.0349(11) 0.0289(11) 0.0121(9) 0.0038(9) 0.0101(9) N9 0.0268(9) 0.0291(9) 0.0299(9) 0.0092(8) 0.0051(7) 0.0097(7) O10 0.0356(9) 0.0290(8) 0.0457(10) 0.0053(8) 0.0154(8) 0.0096(7) C11 0.0291(11) 0.0280(10) 0.0256(10) 0.0069(8) 0.0024(8) 0.0108(9) N12 0.0255(9) 0.0263(8) 0.0285(9) 0.0102(7) 0.0040(7) 0.0078(7) O13 0.0297(9) 0.0254(8) 0.0419(9) 0.0067(7) 0.0112(7) 0.0051(7) N14 0.0238(9) 0.0258(8) 0.0241(8) 0.0082(7) 0.0042(7) 0.0103(7) C15 0.0249(10) 0.0269(10) 0.0256(10) 0.0077(8) 0.0049(8) 0.0100(8) C16 0.0287(11) 0.0297(10) 0.0235(10) 0.0043(8) 0.0019(8) 0.0089(9) C17 0.0301(11) 0.0243(10) 0.0310(11) 0.0071(8) 0.0050(9) 0.0075(8) C18 0.0289(11) 0.0254(10) 0.0285(11) 0.0096(8) 0.0055(9) 0.0094(8) C19 0.0251(10) 0.0269(10) 0.0272(10) 0.0104(8) 0.0064(8) 0.0094(8) C20 0.0276(11) 0.0313(11) 0.0234(10) 0.0082(8) 0.0009(8) 0.0095(9) N21 0.0274(9) 0.0283(9) 0.0266(9) 0.0112(7) 0.0041(7) 0.0100(7) O22 0.0444(10) 0.0275(8) 0.0288(8) 0.0127(7) -0.0001(7) 0.0105(7) C23 0.0264(11) 0.0276(10) 0.0276(10) 0.0112(8) 0.0028(8) 0.0093(8) N24 0.0254(9) 0.0279(9) 0.0242(9) 0.0077(7) 0.0017(7) 0.0089(7) O25 0.0314(9) 0.0280(8) 0.0281(8) 0.0088(7) -0.0021(6) 0.0031(7) Cl26 0.0275(3) 0.0264(2) 0.0249(3) 0.00889(19) 0.0029(2) 0.0070(2) O27 0.0383(9) 0.0287(7) 0.0289(8) 0.0068(6) 0.0090(7) 0.0111(7) O28 0.0279(8) 0.0372(8) 0.0390(9) 0.0117(7) 0.0062(7) 0.0054(7) O29 0.0434(10) 0.0436(9) 0.0316(8) 0.0189(7) 0.0025(7) 0.0147(8) O30 0.0341(9) 0.0244(7) 0.0356(8) 0.0075(6) 0.0048(7) 0.0067(6) Cl31 0.0371(3) 0.0270(3) 0.0283(3) 0.0096(2) 0.0032(2) 0.0104(2) O32 0.0595(12) 0.0304(8) 0.0303(8) 0.0133(7) 0.0011(8) 0.0114(8) O33 0.0420(11) 0.0437(10) 0.0515(11) 0.0022(9) 0.0062(9) 0.0023(8) O34 0.0674(13) 0.0496(11) 0.0702(13) 0.0290(10) 0.0274(11) 0.0388(10) O35 0.0623(12) 0.0427(9) 0.0283(9) 0.0117(7) -0.0039(8) 0.0051(9) O36 0.0338(9) 0.0274(7) 0.0389(9) 0.0106(7) 0.0113(7) 0.0103(6) C37 0.0273(11) 0.0267(10) 0.0355(12) 0.0069(9) 0.0097(9) 0.0102(9) C38 0.0336(12) 0.0285(11) 0.0377(12) 0.0093(9) 0.0068(10) 0.0068(9) C39 0.0389(14) 0.0376(12) 0.0391(13) 0.0095(11) 0.0032(11) 0.0083(10) O40 0.0375(10) 0.0335(8) 0.0333(9) 0.0066(7) 0.0049(7) 0.0110(7) C41 0.0308(12) 0.0315(11) 0.0391(13) 0.0124(10) 0.0100(10) 0.0122(9) C42 0.0479(16) 0.0461(14) 0.0430(14) 0.0187(12) 0.0059(12) 0.0156(12) C43 0.0480(15) 0.0318(12) 0.0409(14) 0.0085(10) 0.0104(11) 0.0068(11) _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 N2 1.9270(17) . ? Cu1 N14 1.9724(17) . ? Cu1 N12 2.1539(18) . ? Cu1 N9 2.1540(18) . ? Cu1 N24 2.3315(17) . ? Cu1 N21 2.3322(17) . ? N2 C7 1.342(3) . ? N2 C3 1.347(3) . ? C3 C4 1.389(3) . ? C3 C8 1.458(3) . ? C4 C5 1.385(3) . ? C5 C6 1.389(3) . ? C6 C7 1.387(3) . ? C7 C11 1.465(3) . ? C8 N9 1.278(3) . ? N9 O10 1.371(2) . ? O10 H10 0.77(2) . ? C11 N12 1.283(3) . ? N12 O13 1.368(2) . ? O13 H13 0.75(2) . ? N14 C15 1.349(3) . ? N14 C19 1.353(3) . ? C15 C16 1.391(3) . ? C15 C20 1.458(3) . ? C16 C17 1.387(3) . ? C17 C18 1.388(3) . ? C18 C19 1.393(3) . ? C19 C23 1.462(3) . ? C20 N21 1.274(3) . ? N21 O22 1.391(2) . ? O22 H22 0.79(2) . ? C23 N24 1.278(3) . ? N24 O25 1.372(2) . ? O25 H25 0.77(2) . ? Cl26 O30 1.4334(15) . ? Cl26 O28 1.4429(17) . ? Cl26 O29 1.4477(16) . ? Cl26 O27 1.4537(16) . ? Cl31 O34 1.4207(19) . ? Cl31 O33 1.4248(19) . ? Cl31 O35 1.4409(17) . ? Cl31 O32 1.4584(16) . ? O36 C37 1.227(3) . ? C37 C39 1.495(3) . ? C37 C38 1.500(3) . ? O40 C41 1.217(3) . ? C41 C43 1.501(3) . ? C41 C42 1.500(3) . ? 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 N2 Cu1 N14 178.69(7) . . ? N2 Cu1 N12 77.77(7) . . ? N14 Cu1 N12 103.53(7) . . ? N2 Cu1 N9 77.74(7) . . ? N14 Cu1 N9 100.96(7) . . ? N12 Cu1 N9 155.46(7) . . ? N2 Cu1 N24 104.00(6) . . ? N14 Cu1 N24 75.91(6) . . ? N12 Cu1 N24 91.76(6) . . ? N9 Cu1 N24 95.66(6) . . ? N2 Cu1 N21 104.85(6) . . ? N14 Cu1 N21 75.23(6) . . ? N12 Cu1 N21 95.34(6) . . ? N9 Cu1 N21 89.37(7) . . ? N24 Cu1 N21 151.13(6) . . ? C7 N2 C3 120.75(18) . . ? C7 N2 Cu1 119.65(14) . . ? C3 N2 Cu1 119.59(14) . . ? N2 C3 C4 121.1(2) . . ? N2 C3 C8 113.38(18) . . ? C4 C3 C8 125.5(2) . . ? C5 C4 C3 118.3(2) . . ? C4 C5 C6 120.3(2) . . ? C7 C6 C5 118.5(2) . . ? N2 C7 C6 121.0(2) . . ? N2 C7 C11 113.72(18) . . ? C6 C7 C11 125.24(19) . . ? N9 C8 C3 116.6(2) . . ? C8 N9 O10 113.28(18) . . ? C8 N9 Cu1 112.65(15) . . ? O10 N9 Cu1 134.02(13) . . ? N9 O10 H10 109(2) . . ? N12 C11 C7 115.98(19) . . ? C11 N12 O13 113.47(17) . . ? C11 N12 Cu1 112.87(15) . . ? O13 N12 Cu1 133.64(12) . . ? N12 O13 H13 109(2) . . ? C15 N14 C19 119.53(17) . . ? C15 N14 Cu1 120.54(13) . . ? C19 N14 Cu1 119.93(14) . . ? N14 C15 C16 121.76(19) . . ? N14 C15 C20 116.38(17) . . ? C16 C15 C20 121.86(18) . . ? C17 C16 C15 118.87(19) . . ? C16 C17 C18 119.43(19) . . ? C17 C18 C19 119.14(19) . . ? N14 C19 C18 121.22(18) . . ? N14 C19 C23 116.37(17) . . ? C18 C19 C23 122.41(18) . . ? N21 C20 C15 117.26(18) . . ? C20 N21 O22 112.48(17) . . ? C20 N21 Cu1 110.51(13) . . ? O22 N21 Cu1 136.89(13) . . ? N21 O22 H22 103(2) . . ? N24 C23 C19 117.78(18) . . ? C23 N24 O25 113.36(16) . . ? C23 N24 Cu1 109.75(13) . . ? O25 N24 Cu1 136.68(12) . . ? N24 O25 H25 107(2) . . ? O30 Cl26 O28 110.41(10) . . ? O30 Cl26 O29 110.01(10) . . ? O28 Cl26 O29 109.26(10) . . ? O30 Cl26 O27 109.56(9) . . ? O28 Cl26 O27 109.05(10) . . ? O29 Cl26 O27 108.51(10) . . ? O34 Cl31 O33 110.30(12) . . ? O34 Cl31 O35 110.71(13) . . ? O33 Cl31 O35 109.77(12) . . ? O34 Cl31 O32 108.76(11) . . ? O33 Cl31 O32 109.60(12) . . ? O35 Cl31 O32 107.64(10) . . ? O36 C37 C39 122.2(2) . . ? O36 C37 C38 119.9(2) . . ? C39 C37 C38 117.9(2) . . ? O40 C41 C43 121.2(2) . . ? O40 C41 C42 122.3(2) . . ? C43 C41 C42 116.4(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O10 H10 O40 0.77(2) 1.91(2) 2.655(2) 163(3) . O13 H13 O36 0.75(2) 1.90(2) 2.642(2) 170(3) . O22 H22 O32 0.79(2) 1.93(2) 2.703(2) 167(3) . O22 H22 O35 0.79(2) 2.61(3) 3.091(2) 121(2) . O25 H25 O27 0.77(2) 2.00(2) 2.758(2) 165(3) . _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.468 _refine_diff_density_min -0.756 _refine_diff_density_rms 0.113