Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global #======================================================================= _journal_coden_Cambridge 186 loop_ _publ_author_name _publ_author_address 'Ying Dong' ; Crystal Structure Analysis Facility School of Chemistry, University of Sydney, Sydney 2006, NSW, Australia. ; 'Geoffrey A. Lawrance' ; Discipline of Chemistry, School of Environmental and Life Sciences, The University of Newcastle, Callaghan 2308, Australia ; 'Leonard F. Lindoy' ; The Centre for Heavy Metal Research, School of Chemistry, University of Sydney, Sydney 2006, NSW, Australia. ; 'Peter Turner' ; Crystal Structure Analysis Facility School of Chemistry, University of Sydney, Sydney 2006, NSW, Australia. ; _publ_contact_author_name 'Leonard F. Lindoy' _publ_contact_author_address ; The Centre for Heavy Metal Research, School of Chemistry, University of Sydney, Sydney 2006, NSW, Australia. ; _publ_contact_author_email Lindoy@chem.usyd.edu.au _publ_contact_author_fax '+61 2 9351 3329' _publ_contact_author_phone '+61 2 9351 4400' _publ_requested_journal 'J. Chem. Soc. Dalton Trans.' _publ_section_title ; Macrocyclic ligand design. Interaction of a series of successively N-benzylated derivatives of 1,4,8,11-tetraazacyclotetradecane (cyclam) with Copper(II) and Nickel(II) ; #======================================================================= # Data block for single structure (one for each study in the paper) #======================================================================= data_lfl24 _database_code_CSD 198031 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17.50 H32 Cu N6 O6.50' _chemical_formula_weight 494.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_Int_Tables_number 15 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' '-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 16.0210(17) _cell_length_b 19.181(2) _cell_length_c 15.6723(16) _cell_angle_alpha 90.00 _cell_angle_beta 104.095(2) _cell_angle_gamma 90.00 _cell_volume 4671.1(8) _cell_formula_units_Z 8 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 991 _cell_measurement_theta_min 2.345 _cell_measurement_theta_max 22.032 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.370 _exptl_crystal_size_mid 0.247 _exptl_crystal_size_min 0.094 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.981 _exptl_absorpt_correction_type 'numerical and empirical' _exptl_absorpt_correction_T_min 0.732 _exptl_absorpt_correction_T_max 0.914 _exptl_absorpt_process_details ; Gaussian (XPREP, Bruker 1995) and SADABS (Sheldrick, 1996) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 109 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.29 _diffrn_reflns_number 24546 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 28.29 _reflns_number_total 5563 _reflns_number_gt 2672 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'teXsan for Windows (MSC, 1997)' _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^)+(0.07P)^2^+10.0P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5563 _refine_ls_number_parameters 280 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1410 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.2226 _refine_ls_wR_factor_gt 0.1784 _refine_ls_goodness_of_fit_ref 1.235 _refine_ls_restrained_S_all 1.239 _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 0.75417(4) 0.49854(3) 0.51582(4) 0.0609(2) Uani 1 1 d . . . N1 N 0.7729(3) 0.6011(2) 0.4858(3) 0.0591(10) Uani 1 1 d . . . N2 N 0.6472(3) 0.4885(2) 0.4197(3) 0.0716(13) Uani 1 1 d . . . H2 H 0.6639 0.4852 0.3683 0.086 Uiso 1 1 calc R . . N3 N 0.7383(3) 0.3966(2) 0.5423(3) 0.0798(14) Uani 1 1 d . . . H3 H 0.7096 0.3967 0.5858 0.096 Uiso 1 1 calc R . . N4 N 0.8607(3) 0.5089(3) 0.6140(3) 0.0782(14) Uani 1 1 d . . . H4 H 0.8423 0.5133 0.6643 0.094 Uiso 1 1 calc R . . C1 C 0.6940(4) 0.6429(3) 0.4663(4) 0.0782(17) Uani 1 1 d . . . H1A H 0.7081 0.6899 0.4520 0.094 Uiso 1 1 calc R . . H1B H 0.6723 0.6454 0.5189 0.094 Uiso 1 1 calc R . . C2 C 0.6232(4) 0.6148(4) 0.3911(4) 0.0854(18) Uani 1 1 d . . . H2A H 0.5778 0.6493 0.3764 0.103 Uiso 1 1 calc R . . H2B H 0.6465 0.6089 0.3399 0.103 Uiso 1 1 calc R . . C3 C 0.5843(4) 0.5468(4) 0.4091(4) 0.0863(18) Uani 1 1 d . . . H3A H 0.5638 0.5511 0.4623 0.104 Uiso 1 1 calc R . . H3B H 0.5352 0.5362 0.3609 0.104 Uiso 1 1 calc R . . C4 C 0.6083(5) 0.4204(4) 0.4335(5) 0.095(2) Uani 1 1 d . . . H4A H 0.5706 0.4047 0.3788 0.114 Uiso 1 1 calc R . . H4B H 0.5742 0.4257 0.4765 0.114 Uiso 1 1 calc R . . C5 C 0.6775(5) 0.3681(4) 0.4652(5) 0.096(2) Uani 1 1 d . . . H5A H 0.6530 0.3251 0.4805 0.115 Uiso 1 1 calc R . . H5B H 0.7069 0.3581 0.4192 0.115 Uiso 1 1 calc R . . C6 C 0.8144(5) 0.3516(3) 0.5754(5) 0.095(2) Uani 1 1 d . . . H6A H 0.8421 0.3427 0.5278 0.114 Uiso 1 1 calc R . . H6B H 0.7955 0.3072 0.5936 0.114 Uiso 1 1 calc R . . C7 C 0.8787(5) 0.3832(4) 0.6511(5) 0.104(2) Uani 1 1 d . . . H7A H 0.9231 0.3491 0.6740 0.125 Uiso 1 1 calc R . . H7B H 0.8501 0.3939 0.6975 0.125 Uiso 1 1 calc R . . C8 C 0.9210(4) 0.4491(4) 0.6284(4) 0.096(2) Uani 1 1 d . . . H8A H 0.9706 0.4601 0.6759 0.115 Uiso 1 1 calc R . . H8B H 0.9411 0.4412 0.5756 0.115 Uiso 1 1 calc R . . C9 C 0.9019(5) 0.5750(4) 0.6024(4) 0.092(2) Uani 1 1 d . . . H9A H 0.9378 0.5692 0.5611 0.110 Uiso 1 1 calc R . . H9B H 0.9381 0.5905 0.6581 0.110 Uiso 1 1 calc R . . C10 C 0.8332(5) 0.6278(3) 0.5681(4) 0.0840(18) Uani 1 1 d . . . H10A H 0.8592 0.6711 0.5557 0.101 Uiso 1 1 calc R . . H10B H 0.8014 0.6370 0.6123 0.101 Uiso 1 1 calc R . . C11 C 0.8160(4) 0.6012(3) 0.4104(3) 0.0651(13) Uani 1 1 d . . . H11A H 0.7762 0.5815 0.3594 0.078 Uiso 1 1 calc R . . H11B H 0.8655 0.5705 0.4255 0.078 Uiso 1 1 calc R . . C12 C 0.8459(4) 0.6715(3) 0.3846(4) 0.0688(14) Uani 1 1 d . . . C13 C 0.7942(5) 0.7120(3) 0.3220(4) 0.0832(17) Uani 1 1 d . . . H13 H 0.7383 0.6977 0.2963 0.100 Uiso 1 1 calc R . . C14 C 0.8251(6) 0.7759(4) 0.2959(5) 0.097(2) Uani 1 1 d . . . H14 H 0.7898 0.8029 0.2524 0.117 Uiso 1 1 calc R . . C15 C 0.9049(6) 0.7974(4) 0.3336(7) 0.107(2) Uani 1 1 d . . . H15 H 0.9247 0.8396 0.3170 0.128 Uiso 1 1 calc R . . C16 C 0.9576(6) 0.7573(4) 0.3968(7) 0.122(3) Uani 1 1 d . . . H16 H 1.0128 0.7727 0.4237 0.147 Uiso 1 1 calc R . . C17 C 0.9290(5) 0.6945(3) 0.4203(5) 0.098(2) Uani 1 1 d . . . H17 H 0.9663 0.6666 0.4611 0.118 Uiso 1 1 calc R . . O1 O 0.8550(5) 0.4362(3) 0.4137(4) 0.137(2) Uani 1 1 d . . . O2 O 0.8602(8) 0.3842(5) 0.2954(7) 0.250(5) Uani 1 1 d . . . O3 O 0.8691(10) 0.4824(5) 0.2982(6) 0.270(7) Uani 1 1 d . . . N5 N 0.8578(5) 0.4318(4) 0.3415(5) 0.111(2) Uani 1 1 d . . . O4 O 0.6615(3) 0.5331(3) 0.6141(3) 0.1013(15) Uani 1 1 d . . . O5 O 0.6163(4) 0.5348(3) 0.7313(3) 0.131(2) Uani 1 1 d . . . O6 O 0.6706(5) 0.4445(4) 0.6941(4) 0.143(2) Uani 1 1 d . . . N6 N 0.6550(4) 0.5077(3) 0.6832(4) 0.0883(16) Uani 1 1 d . . . O7 O 0.8715(10) 0.2618(8) 0.3987(10) 0.166(5) Uiso 0.50 1 d PD . . H7O H 0.8613 0.3007 0.3768 0.249 Uiso 0.50 1 calc PR . . C18 C 0.9236(12) 0.2253(10) 0.3547(12) 0.134(6) Uiso 0.50 1 d PD . . H18A H 0.9255 0.2496 0.3016 0.202 Uiso 0.50 1 calc PR . . H18B H 0.9006 0.1794 0.3403 0.202 Uiso 0.50 1 calc PR . . H18C H 0.9808 0.2218 0.3918 0.202 Uiso 0.50 1 calc PR . . 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 0.0756(4) 0.0596(4) 0.0468(3) -0.0010(3) 0.0138(3) -0.0074(3) N1 0.078(3) 0.055(2) 0.047(2) -0.0060(18) 0.022(2) -0.005(2) N2 0.074(3) 0.090(3) 0.054(3) -0.007(2) 0.023(2) -0.020(3) N3 0.114(4) 0.070(3) 0.065(3) 0.003(2) 0.041(3) -0.009(3) N4 0.093(3) 0.091(4) 0.046(2) 0.001(2) 0.008(2) -0.004(3) C1 0.101(5) 0.073(4) 0.074(4) 0.000(3) 0.047(4) 0.010(3) C2 0.080(4) 0.102(5) 0.076(4) 0.014(4) 0.024(3) 0.021(4) C3 0.067(4) 0.117(6) 0.076(4) 0.002(4) 0.020(3) 0.001(4) C4 0.104(5) 0.102(5) 0.081(4) -0.006(4) 0.025(4) -0.045(4) C5 0.124(6) 0.078(4) 0.091(5) -0.019(4) 0.036(4) -0.033(4) C6 0.130(6) 0.068(4) 0.096(5) 0.010(4) 0.044(5) 0.014(4) C7 0.136(6) 0.101(5) 0.080(5) 0.029(4) 0.038(5) 0.036(5) C8 0.095(5) 0.120(6) 0.068(4) 0.017(4) 0.013(3) 0.018(4) C9 0.102(5) 0.098(5) 0.067(4) -0.005(3) 0.004(3) -0.031(4) C10 0.115(5) 0.077(4) 0.060(4) -0.020(3) 0.022(3) -0.027(4) C11 0.083(4) 0.060(3) 0.057(3) -0.007(2) 0.027(3) -0.002(3) C12 0.083(4) 0.061(3) 0.071(4) -0.006(3) 0.035(3) 0.001(3) C13 0.109(5) 0.079(4) 0.070(4) 0.001(3) 0.037(4) -0.005(4) C14 0.138(7) 0.079(4) 0.087(5) 0.016(4) 0.052(5) 0.014(5) C15 0.124(7) 0.070(4) 0.145(7) 0.000(5) 0.068(6) -0.013(5) C16 0.110(6) 0.098(6) 0.167(9) 0.008(6) 0.047(6) -0.023(5) C17 0.084(5) 0.076(4) 0.138(6) 0.008(4) 0.032(4) -0.009(4) O1 0.220(7) 0.120(4) 0.092(4) 0.013(3) 0.076(4) -0.003(4) O2 0.375(15) 0.177(9) 0.194(10) -0.040(7) 0.062(10) -0.028(9) O3 0.55(2) 0.155(8) 0.147(8) 0.006(6) 0.169(11) 0.014(10) N5 0.152(6) 0.088(5) 0.093(5) -0.016(4) 0.029(4) -0.013(4) O4 0.153(4) 0.103(3) 0.066(3) 0.014(2) 0.060(3) 0.020(3) O5 0.206(6) 0.130(4) 0.080(3) 0.016(3) 0.082(4) 0.039(4) O6 0.201(6) 0.134(5) 0.119(5) 0.037(4) 0.087(5) 0.043(5) N6 0.120(4) 0.088(4) 0.067(3) 0.016(3) 0.042(3) 0.015(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 1.997(5) . ? Cu1 N4 2.010(5) . ? Cu1 N3 2.027(5) . ? Cu1 N1 2.061(4) . ? Cu1 O4 2.476(4) . ? Cu1 O1 2.804(6) . ? N1 C1 1.465(7) . ? N1 C10 1.501(7) . ? N1 C11 1.505(6) . ? N2 C4 1.485(7) . ? N2 C3 1.487(8) . ? N2 H2 0.9100 . ? N3 C5 1.462(8) . ? N3 C6 1.481(8) . ? N3 H3 0.9100 . ? N4 C9 1.462(7) . ? N4 C8 1.480(8) . ? N4 H4 0.9100 . ? C1 C2 1.522(9) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.502(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.489(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.498(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.515(10) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.496(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.519(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.362(8) . ? C12 C17 1.386(8) . ? C13 C14 1.419(9) . ? C13 H13 0.9300 . ? C14 C15 1.336(11) . ? C14 H14 0.9300 . ? C15 C16 1.370(12) . ? C15 H15 0.9300 . ? C16 C17 1.371(9) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? O1 N5 1.146(8) . ? O2 N5 1.172(10) . ? O3 N5 1.222(10) . ? O4 N6 1.214(6) . ? O5 N6 1.205(7) . ? O6 N6 1.241(7) . ? O7 C18 1.394(15) . ? O7 H7O 0.8200 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N4 179.07(19) . . ? N2 Cu1 N3 86.2(2) . . ? N4 Cu1 N3 93.6(2) . . ? N2 Cu1 N1 93.77(18) . . ? N4 Cu1 N1 86.40(18) . . ? N3 Cu1 N1 177.93(17) . . ? N2 Cu1 O4 87.74(18) . . ? N4 Cu1 O4 91.34(19) . . ? N3 Cu1 O4 90.37(18) . . ? N1 Cu1 O4 91.70(16) . . ? N2 Cu1 O1 92.1(2) . . ? N4 Cu1 O1 88.8(2) . . ? N3 Cu1 O1 79.88(18) . . ? N1 Cu1 O1 98.05(16) . . ? O4 Cu1 O1 170.24(16) . . ? C1 N1 C10 109.5(5) . . ? C1 N1 C11 111.9(4) . . ? C10 N1 C11 110.6(4) . . ? C1 N1 Cu1 113.8(3) . . ? C10 N1 Cu1 103.2(3) . . ? C11 N1 Cu1 107.5(3) . . ? C4 N2 C3 112.3(5) . . ? C4 N2 Cu1 106.7(4) . . ? C3 N2 Cu1 116.5(4) . . ? C4 N2 H2 106.9 . . ? C3 N2 H2 106.9 . . ? Cu1 N2 H2 106.9 . . ? C5 N3 C6 113.4(6) . . ? C5 N3 Cu1 106.4(4) . . ? C6 N3 Cu1 120.0(4) . . ? C5 N3 H3 105.3 . . ? C6 N3 H3 105.3 . . ? Cu1 N3 H3 105.3 . . ? C9 N4 C8 113.2(6) . . ? C9 N4 Cu1 108.4(4) . . ? C8 N4 Cu1 116.2(4) . . ? C9 N4 H4 106.1 . . ? C8 N4 H4 106.1 . . ? Cu1 N4 H4 106.1 . . ? N1 C1 C2 114.2(5) . . ? N1 C1 H1A 108.7 . . ? C2 C1 H1A 108.7 . . ? N1 C1 H1B 108.7 . . ? C2 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? C3 C2 C1 115.3(5) . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2B 108.5 . . ? C1 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? N2 C3 C2 111.9(5) . . ? N2 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? N2 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N2 C4 C5 109.6(5) . . ? N2 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? N2 C4 H4B 109.7 . . ? C5 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? N3 C5 C4 108.4(5) . . ? N3 C5 H5A 110.0 . . ? C4 C5 H5A 110.0 . . ? N3 C5 H5B 110.0 . . ? C4 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? N3 C6 C7 112.9(5) . . ? N3 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? N3 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C6 C7 C8 114.3(6) . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? N4 C8 C7 111.7(6) . . ? N4 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? N4 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? N4 C9 C10 108.4(5) . . ? N4 C9 H9A 110.0 . . ? C10 C9 H9A 110.0 . . ? N4 C9 H9B 110.0 . . ? C10 C9 H9B 110.0 . . ? H9A C9 H9B 108.4 . . ? C9 C10 N1 109.9(5) . . ? C9 C10 H10A 109.7 . . ? N1 C10 H10A 109.7 . . ? C9 C10 H10B 109.7 . . ? N1 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? N1 C11 C12 116.4(4) . . ? N1 C11 H11A 108.2 . . ? C12 C11 H11A 108.2 . . ? N1 C11 H11B 108.2 . . ? C12 C11 H11B 108.2 . . ? H11A C11 H11B 107.3 . . ? C13 C12 C17 117.7(6) . . ? C13 C12 C11 121.6(6) . . ? C17 C12 C11 120.6(6) . . ? C12 C13 C14 120.5(7) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 120.1(7) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.2(7) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C17 120.0(8) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 121.5(7) . . ? C16 C17 H17 119.2 . . ? C12 C17 H17 119.2 . . ? N5 O1 Cu1 139.6(6) . . ? O1 N5 O2 133.0(10) . . ? O1 N5 O3 122.5(8) . . ? O2 N5 O3 104.1(10) . . ? N6 O4 Cu1 129.9(4) . . ? O5 N6 O4 123.7(6) . . ? O5 N6 O6 116.9(6) . . ? O4 N6 O6 117.2(6) . . ? C18 O7 H7O 109.5 . . ? O7 C18 H18A 109.5 . . ? O7 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O7 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 N1 C1 42.8(4) . . . . ? N4 Cu1 N1 C1 -136.2(4) . . . . ? N3 Cu1 N1 C1 133(5) . . . . ? O4 Cu1 N1 C1 -45.0(4) . . . . ? O1 Cu1 N1 C1 135.5(4) . . . . ? N2 Cu1 N1 C10 161.4(4) . . . . ? N4 Cu1 N1 C10 -17.7(4) . . . . ? N3 Cu1 N1 C10 -108(6) . . . . ? O4 Cu1 N1 C10 73.6(4) . . . . ? O1 Cu1 N1 C10 -106.0(4) . . . . ? N2 Cu1 N1 C11 -81.6(3) . . . . ? N4 Cu1 N1 C11 99.3(3) . . . . ? N3 Cu1 N1 C11 8(6) . . . . ? O4 Cu1 N1 C11 -169.5(3) . . . . ? O1 Cu1 N1 C11 11.0(4) . . . . ? N4 Cu1 N2 C4 -71(12) . . . . ? N3 Cu1 N2 C4 11.4(4) . . . . ? N1 Cu1 N2 C4 -170.7(4) . . . . ? O4 Cu1 N2 C4 -79.1(4) . . . . ? O1 Cu1 N2 C4 91.1(4) . . . . ? N4 Cu1 N2 C3 56(12) . . . . ? N3 Cu1 N2 C3 137.8(4) . . . . ? N1 Cu1 N2 C3 -44.3(4) . . . . ? O4 Cu1 N2 C3 47.3(4) . . . . ? O1 Cu1 N2 C3 -142.5(4) . . . . ? N2 Cu1 N3 C5 16.4(4) . . . . ? N4 Cu1 N3 C5 -164.5(4) . . . . ? N1 Cu1 N3 C5 -74(6) . . . . ? O4 Cu1 N3 C5 104.1(4) . . . . ? O1 Cu1 N3 C5 -76.4(4) . . . . ? N2 Cu1 N3 C6 146.8(5) . . . . ? N4 Cu1 N3 C6 -34.1(5) . . . . ? N1 Cu1 N3 C6 57(6) . . . . ? O4 Cu1 N3 C6 -125.5(5) . . . . ? O1 Cu1 N3 C6 54.0(5) . . . . ? N2 Cu1 N4 C9 -110(12) . . . . ? N3 Cu1 N4 C9 167.6(4) . . . . ? N1 Cu1 N4 C9 -10.3(4) . . . . ? O4 Cu1 N4 C9 -101.9(4) . . . . ? O1 Cu1 N4 C9 87.9(4) . . . . ? N2 Cu1 N4 C8 121(12) . . . . ? N3 Cu1 N4 C8 39.0(5) . . . . ? N1 Cu1 N4 C8 -139.0(4) . . . . ? O4 Cu1 N4 C8 129.4(4) . . . . ? O1 Cu1 N4 C8 -40.8(4) . . . . ? C10 N1 C1 C2 -172.3(5) . . . . ? C11 N1 C1 C2 64.6(6) . . . . ? Cu1 N1 C1 C2 -57.5(5) . . . . ? N1 C1 C2 C3 67.7(7) . . . . ? C4 N2 C3 C2 -177.4(5) . . . . ? Cu1 N2 C3 C2 59.0(6) . . . . ? C1 C2 C3 N2 -66.3(7) . . . . ? C3 N2 C4 C5 -166.2(5) . . . . ? Cu1 N2 C4 C5 -37.4(6) . . . . ? C6 N3 C5 C4 -175.1(5) . . . . ? Cu1 N3 C5 C4 -41.0(6) . . . . ? N2 C4 C5 N3 53.4(7) . . . . ? C5 N3 C6 C7 176.6(6) . . . . ? Cu1 N3 C6 C7 49.4(7) . . . . ? N3 C6 C7 C8 -65.3(8) . . . . ? C9 N4 C8 C7 173.1(5) . . . . ? Cu1 N4 C8 C7 -60.6(6) . . . . ? C6 C7 C8 N4 72.4(8) . . . . ? C8 N4 C9 C10 167.1(5) . . . . ? Cu1 N4 C9 C10 36.8(6) . . . . ? N4 C9 C10 N1 -55.0(7) . . . . ? C1 N1 C10 C9 164.5(5) . . . . ? C11 N1 C10 C9 -71.7(6) . . . . ? Cu1 N1 C10 C9 43.0(5) . . . . ? C1 N1 C11 C12 61.6(6) . . . . ? C10 N1 C11 C12 -60.8(6) . . . . ? Cu1 N1 C11 C12 -172.8(4) . . . . ? N1 C11 C12 C13 -91.4(6) . . . . ? N1 C11 C12 C17 92.7(7) . . . . ? C17 C12 C13 C14 -0.9(9) . . . . ? C11 C12 C13 C14 -176.8(5) . . . . ? C12 C13 C14 C15 -1.1(10) . . . . ? C13 C14 C15 C16 1.0(12) . . . . ? C14 C15 C16 C17 1.1(13) . . . . ? C15 C16 C17 C12 -3.1(13) . . . . ? C13 C12 C17 C16 3.0(10) . . . . ? C11 C12 C17 C16 179.0(7) . . . . ? N2 Cu1 O1 N5 32.5(9) . . . . ? N4 Cu1 O1 N5 -147.8(9) . . . . ? N3 Cu1 O1 N5 118.3(9) . . . . ? N1 Cu1 O1 N5 -61.6(9) . . . . ? O4 Cu1 O1 N5 121.2(11) . . . . ? Cu1 O1 N5 O2 -125.6(13) . . . . ? Cu1 O1 N5 O3 63.3(16) . . . . ? N2 Cu1 O4 N6 122.8(6) . . . . ? N4 Cu1 O4 N6 -57.1(6) . . . . ? N3 Cu1 O4 N6 36.6(6) . . . . ? N1 Cu1 O4 N6 -143.5(6) . . . . ? O1 Cu1 O4 N6 33.7(15) . . . . ? Cu1 O4 N6 O5 169.4(6) . . . . ? Cu1 O4 N6 O6 -28.5(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7O O2 0.82 2.05 2.832(18) 160.5 . O7 H7O N5 0.82 2.57 3.375(17) 166.0 . N2 H2 O5 0.91 2.13 2.907(7) 142.6 6_565 N4 H4 O3 0.91 2.04 2.862(10) 149.7 6_566 N3 H3 O6 0.91 2.15 2.989(7) 152.6 . _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.707 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.091 #===END data_lfl22 _database_code_CSD 198032 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H40 Cu N6 O7' _chemical_formula_weight 600.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.316(3) _cell_length_b 18.311(4) _cell_length_c 12.303(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.132(4) _cell_angle_gamma 90.00 _cell_volume 2758.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1005 _cell_measurement_theta_min 2.778 _cell_measurement_theta_max 28.010 _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.331 _exptl_crystal_size_mid 0.287 _exptl_crystal_size_min 0.177 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1268 _exptl_absorpt_coefficient_mu 0.846 _exptl_absorpt_correction_type 'numerical and empirical' _exptl_absorpt_correction_T_min 0.744 _exptl_absorpt_correction_T_max 0.878 _exptl_absorpt_process_details ; Gaussian (XPREP, Bruker 1995) and SADABS (Sheldrick, 1996) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 313 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.000 _diffrn_reflns_number 28625 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0153 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 28.30 _reflns_number_total 6560 _reflns_number_gt 5778 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'teXsan for Windows (MSC, 1997)' _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^)+(0.0517P)^2^+1.0804P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6560 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.171532(13) 0.621556(9) 0.298811(15) 0.02031(7) Uani 1 1 d . . . O1 O 0.23523(10) 0.58789(7) 0.53277(12) 0.0375(3) Uani 1 1 d . . . O2 O 0.26468(13) 0.53605(10) 0.70082(15) 0.0679(5) Uani 1 1 d . . . O3 O 0.10061(9) 0.54778(7) 0.57242(11) 0.0368(3) Uani 1 1 d . . . O4 O 0.13893(10) 0.64007(6) 0.08075(10) 0.0311(2) Uani 1 1 d . . . O5 O 0.02945(12) 0.57675(8) -0.06512(12) 0.0522(4) Uani 1 1 d . . . O6 O 0.18185(11) 0.52933(7) 0.05153(11) 0.0393(3) Uani 1 1 d . . . O7 O 0.46678(12) 0.58974(13) 0.66538(14) 0.0681(5) Uani 1 1 d . . . H7 H 0.4041 0.5723 0.6485 0.102 Uiso 1 1 calc R . . N1 N 0.02848(9) 0.67648(6) 0.27510(10) 0.0200(2) Uani 1 1 d . . . N2 N 0.27114(10) 0.71293(7) 0.33530(10) 0.0221(2) Uani 1 1 d . . . N3 N 0.30497(10) 0.56429(7) 0.30999(11) 0.0267(3) Uani 1 1 d . . . H3 H 0.2948 0.5540 0.2323 0.032 Uiso 1 1 calc R . . N4 N 0.07922(10) 0.52976(7) 0.25301(11) 0.0237(2) Uani 1 1 d . . . H4 H 0.0697 0.5192 0.1757 0.028 Uiso 1 1 calc R . . N5 N 0.19983(11) 0.55658(7) 0.60220(12) 0.0287(3) Uani 1 1 d . . . N6 N 0.11651(11) 0.58148(7) 0.02134(11) 0.0267(3) Uani 1 1 d . . . C1 C 0.01572(12) 0.74666(8) 0.20886(13) 0.0248(3) Uani 1 1 d . . . H1A H -0.0526 0.7706 0.2041 0.030 Uiso 1 1 calc R . . H1B H 0.0077 0.7354 0.1271 0.030 Uiso 1 1 calc R . . C2 C 0.10967(13) 0.80042(8) 0.26256(14) 0.0277(3) Uani 1 1 d . . . H2A H 0.1217 0.8086 0.3463 0.033 Uiso 1 1 calc R . . H2B H 0.0881 0.8477 0.2208 0.033 Uiso 1 1 calc R . . C3 C 0.21702(13) 0.77598(8) 0.25707(13) 0.0262(3) Uani 1 1 d . . . H3A H 0.2031 0.7626 0.1744 0.031 Uiso 1 1 calc R . . H3B H 0.2681 0.8179 0.2788 0.031 Uiso 1 1 calc R . . C4 C 0.36481(12) 0.68846(9) 0.30629(14) 0.0282(3) Uani 1 1 d . . . H4A H 0.4262 0.7232 0.3402 0.034 Uiso 1 1 calc R . . H4B H 0.3424 0.6878 0.2195 0.034 Uiso 1 1 calc R . . C5 C 0.40155(13) 0.61289(10) 0.35562(15) 0.0314(3) Uani 1 1 d . . . H5A H 0.4591 0.5949 0.3302 0.038 Uiso 1 1 calc R . . H5B H 0.4316 0.6141 0.4431 0.038 Uiso 1 1 calc R . . C6 C 0.32555(14) 0.49239(9) 0.37133(15) 0.0338(4) Uani 1 1 d . . . H6A H 0.3366 0.4996 0.4550 0.041 Uiso 1 1 calc R . . H6B H 0.3931 0.4707 0.3697 0.041 Uiso 1 1 calc R . . C7 C 0.23098(15) 0.44032(9) 0.31322(16) 0.0354(4) Uani 1 1 d . . . H7A H 0.2522 0.3915 0.3495 0.042 Uiso 1 1 calc R . . H7B H 0.2178 0.4359 0.2285 0.042 Uiso 1 1 calc R . . C8 C 0.12469(14) 0.46282(8) 0.32288(14) 0.0304(3) Uani 1 1 d . . . H8A H 0.0710 0.4226 0.2939 0.036 Uiso 1 1 calc R . . H8B H 0.1382 0.4718 0.4068 0.036 Uiso 1 1 calc R . . C9 C -0.03021(12) 0.54805(8) 0.24952(14) 0.0272(3) Uani 1 1 d . . . H9A H -0.0300 0.5460 0.3300 0.033 Uiso 1 1 calc R . . H9B H -0.0852 0.5129 0.1987 0.033 Uiso 1 1 calc R . . C10 C -0.05707(12) 0.62415(8) 0.20004(13) 0.0244(3) Uani 1 1 d . . . H10A H -0.0606 0.6251 0.1181 0.029 Uiso 1 1 calc R . . H10B H -0.1293 0.6389 0.1980 0.029 Uiso 1 1 calc R . . C11 C 0.02118(11) 0.68749(8) 0.39353(12) 0.0215(3) Uani 1 1 d . . . H11A H 0.0704 0.7283 0.4343 0.026 Uiso 1 1 calc R . . H11B H 0.0498 0.6430 0.4414 0.026 Uiso 1 1 calc R . . C12 C -0.09067(11) 0.70356(8) 0.39336(12) 0.0221(3) Uani 1 1 d . . . C13 C -0.15404(13) 0.64693(9) 0.40839(14) 0.0293(3) Uani 1 1 d . . . H13 H -0.1296 0.5979 0.4120 0.035 Uiso 1 1 calc R . . C14 C -0.25267(14) 0.66149(10) 0.41819(16) 0.0351(4) Uani 1 1 d . . . H14 H -0.2961 0.6224 0.4264 0.042 Uiso 1 1 calc R . . C15 C -0.28757(13) 0.73271(11) 0.41592(16) 0.0373(4) Uani 1 1 d . . . H15 H -0.3544 0.7427 0.4238 0.045 Uiso 1 1 calc R . . C16 C -0.22504(14) 0.78949(10) 0.40213(16) 0.0360(4) Uani 1 1 d . . . H16 H -0.2489 0.8385 0.4010 0.043 Uiso 1 1 calc R . . C17 C -0.12715(13) 0.77506(9) 0.38987(14) 0.0276(3) Uani 1 1 d . . . H17 H -0.0852 0.8142 0.3791 0.033 Uiso 1 1 calc R . . C18 C 0.30978(12) 0.73268(8) 0.46456(13) 0.0248(3) Uani 1 1 d . . . H18A H 0.3378 0.6878 0.5115 0.030 Uiso 1 1 calc R . . H18B H 0.2457 0.7491 0.4798 0.030 Uiso 1 1 calc R . . C19 C 0.39713(13) 0.79096(9) 0.51025(13) 0.0278(3) Uani 1 1 d . . . C20 C 0.50663(14) 0.77098(11) 0.56744(14) 0.0354(4) Uani 1 1 d . . . H20 H 0.5266 0.7209 0.5730 0.043 Uiso 1 1 calc R . . C21 C 0.58696(16) 0.82402(13) 0.61643(17) 0.0473(5) Uani 1 1 d . . . H21 H 0.6614 0.8100 0.6541 0.057 Uiso 1 1 calc R . . C22 C 0.55874(19) 0.89691(13) 0.61034(18) 0.0518(6) Uani 1 1 d . . . H22 H 0.6136 0.9329 0.6443 0.062 Uiso 1 1 calc R . . C23 C 0.45099(18) 0.91725(11) 0.55492(18) 0.0477(5) Uani 1 1 d . . . H23 H 0.4316 0.9674 0.5511 0.057 Uiso 1 1 calc R . . C24 C 0.36978(16) 0.86472(10) 0.50415(16) 0.0355(4) Uani 1 1 d . . . H24 H 0.2957 0.8794 0.4654 0.043 Uiso 1 1 calc R . . C25 C 0.51315(18) 0.60551(14) 0.7834(2) 0.0524(5) Uani 1 1 d . . . H25A H 0.5870 0.5850 0.8176 0.079 Uiso 1 1 calc R . . H25B H 0.4688 0.5843 0.8228 0.079 Uiso 1 1 calc R . . H25C H 0.5169 0.6586 0.7944 0.079 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 0.01969(10) 0.01788(10) 0.02365(10) -0.00258(6) 0.00883(7) -0.00085(6) O1 0.0330(6) 0.0380(7) 0.0478(7) 0.0025(5) 0.0224(5) -0.0027(5) O2 0.0450(8) 0.0725(11) 0.0568(9) 0.0304(8) -0.0117(7) -0.0096(8) O3 0.0290(6) 0.0387(7) 0.0426(7) 0.0113(5) 0.0139(5) -0.0037(5) O4 0.0383(6) 0.0273(5) 0.0268(5) -0.0076(4) 0.0118(5) -0.0040(5) O5 0.0549(8) 0.0377(7) 0.0389(7) -0.0120(6) -0.0086(6) 0.0031(6) O6 0.0464(7) 0.0343(6) 0.0364(6) -0.0039(5) 0.0153(6) 0.0095(6) O7 0.0322(7) 0.1233(17) 0.0500(9) -0.0133(10) 0.0176(7) -0.0034(9) N1 0.0212(5) 0.0203(6) 0.0189(5) 0.0001(4) 0.0083(4) -0.0001(4) N2 0.0228(6) 0.0245(6) 0.0213(6) -0.0038(5) 0.0112(5) -0.0043(5) N3 0.0255(6) 0.0281(6) 0.0264(6) -0.0043(5) 0.0099(5) 0.0034(5) N4 0.0287(6) 0.0195(6) 0.0239(6) -0.0020(5) 0.0115(5) -0.0021(5) N5 0.0288(6) 0.0185(6) 0.0340(7) 0.0002(5) 0.0071(5) -0.0023(5) N6 0.0343(7) 0.0282(6) 0.0203(6) -0.0024(5) 0.0136(5) -0.0035(5) C1 0.0284(7) 0.0236(7) 0.0229(7) 0.0055(5) 0.0106(6) 0.0032(6) C2 0.0364(8) 0.0198(7) 0.0296(7) 0.0029(6) 0.0159(6) 0.0008(6) C3 0.0333(8) 0.0240(7) 0.0243(7) -0.0003(5) 0.0147(6) -0.0058(6) C4 0.0251(7) 0.0367(8) 0.0274(7) -0.0079(6) 0.0153(6) -0.0066(6) C5 0.0218(7) 0.0412(9) 0.0317(8) -0.0079(7) 0.0108(6) 0.0017(6) C6 0.0354(8) 0.0311(8) 0.0329(8) -0.0007(7) 0.0113(7) 0.0120(7) C7 0.0486(10) 0.0213(7) 0.0346(8) -0.0017(6) 0.0145(7) 0.0077(7) C8 0.0402(9) 0.0211(7) 0.0286(7) 0.0005(6) 0.0122(7) -0.0023(6) C9 0.0275(7) 0.0265(7) 0.0299(7) -0.0048(6) 0.0138(6) -0.0079(6) C10 0.0206(6) 0.0291(8) 0.0218(7) -0.0037(5) 0.0066(5) -0.0037(5) C11 0.0219(6) 0.0245(7) 0.0182(6) 0.0007(5) 0.0081(5) 0.0010(5) C12 0.0222(6) 0.0269(7) 0.0169(6) 0.0009(5) 0.0074(5) 0.0015(5) C13 0.0323(8) 0.0284(8) 0.0310(8) 0.0038(6) 0.0165(7) 0.0014(6) C14 0.0296(8) 0.0443(10) 0.0361(9) 0.0051(7) 0.0179(7) -0.0030(7) C15 0.0264(8) 0.0543(11) 0.0351(9) 0.0063(8) 0.0162(7) 0.0087(7) C16 0.0353(9) 0.0380(9) 0.0375(9) 0.0051(7) 0.0172(7) 0.0140(7) C17 0.0296(7) 0.0271(7) 0.0274(7) 0.0026(6) 0.0125(6) 0.0030(6) C18 0.0278(7) 0.0281(7) 0.0212(6) -0.0040(5) 0.0125(6) -0.0070(6) C19 0.0324(8) 0.0346(8) 0.0208(7) -0.0077(6) 0.0152(6) -0.0121(6) C20 0.0336(8) 0.0457(10) 0.0254(7) -0.0037(7) 0.0098(7) -0.0108(7) C21 0.0379(9) 0.0690(14) 0.0304(9) -0.0076(9) 0.0084(7) -0.0227(9) C22 0.0574(13) 0.0614(13) 0.0368(10) -0.0176(9) 0.0186(9) -0.0378(11) C23 0.0659(13) 0.0381(10) 0.0476(11) -0.0171(8) 0.0314(10) -0.0245(9) C24 0.0429(9) 0.0347(9) 0.0360(9) -0.0113(7) 0.0231(8) -0.0127(7) C25 0.0400(10) 0.0680(14) 0.0476(12) -0.0110(10) 0.0156(9) -0.0058(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 N3 2.0207(13) . ? Cu1 N4 2.0272(13) . ? Cu1 N1 2.0708(12) . ? Cu1 N2 2.0719(12) . ? Cu1 O4 2.5663(13) . ? Cu1 O1 2.7325(15) . ? O1 N5 1.2635(18) . ? O2 N5 1.2394(19) . ? O3 N5 1.2351(18) . ? O4 N6 1.2661(17) . ? O5 N6 1.2305(18) . ? O6 N6 1.2462(18) . ? O7 C25 1.367(3) . ? O7 H7 0.8400 . ? N1 C1 1.4951(18) . ? N1 C10 1.4975(18) . ? N1 C11 1.5113(18) . ? N2 C3 1.4946(19) . ? N2 C4 1.4946(19) . ? N2 C18 1.5105(18) . ? N3 C5 1.481(2) . ? N3 C6 1.489(2) . ? N3 H3 0.9300 . ? N4 C9 1.479(2) . ? N4 C8 1.4829(19) . ? N4 H4 0.9300 . ? C1 C2 1.524(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.524(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.513(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.516(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.523(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.506(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5174(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C17 1.391(2) . ? C12 C13 1.394(2) . ? C13 C14 1.391(2) . ? C13 H13 0.9500 . ? C14 C15 1.381(3) . ? C14 H14 0.9500 . ? C15 C16 1.384(3) . ? C15 H15 0.9500 . ? C16 C17 1.395(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.515(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.393(2) . ? C19 C20 1.396(2) . ? C20 C21 1.394(3) . ? C20 H20 0.9500 . ? C21 C22 1.381(3) . ? C21 H21 0.9500 . ? C22 C23 1.376(3) . ? C22 H22 0.9500 . ? C23 C24 1.398(2) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? 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 N4 90.55(5) . . ? N3 Cu1 N1 175.66(5) . . ? N4 Cu1 N1 86.55(5) . . ? N3 Cu1 N2 86.18(5) . . ? N4 Cu1 N2 175.21(5) . . ? N1 Cu1 N2 96.51(5) . . ? N3 Cu1 O4 85.57(5) . . ? N4 Cu1 O4 89.08(4) . . ? N1 Cu1 O4 91.15(4) . . ? N2 Cu1 O4 87.18(4) . . ? N3 Cu1 O1 84.86(5) . . ? N4 Cu1 O1 90.52(4) . . ? N1 Cu1 O1 98.37(4) . . ? N2 Cu1 O1 92.67(4) . . ? O4 Cu1 O1 170.42(4) . . ? N5 O1 Cu1 140.41(10) . . ? N6 O4 Cu1 113.35(9) . . ? C25 O7 H7 109.5 . . ? C1 N1 C10 108.53(11) . . ? C1 N1 C11 111.98(11) . . ? C10 N1 C11 111.00(11) . . ? C1 N1 Cu1 113.30(9) . . ? C10 N1 Cu1 102.17(9) . . ? C11 N1 Cu1 109.45(8) . . ? C3 N2 C4 108.32(11) . . ? C3 N2 C18 111.82(11) . . ? C4 N2 C18 110.62(11) . . ? C3 N2 Cu1 112.25(9) . . ? C4 N2 Cu1 103.26(9) . . ? C18 N2 Cu1 110.23(9) . . ? C5 N3 C6 112.32(13) . . ? C5 N3 Cu1 108.87(10) . . ? C6 N3 Cu1 118.38(10) . . ? C5 N3 H3 105.4 . . ? C6 N3 H3 105.4 . . ? Cu1 N3 H3 105.4 . . ? C9 N4 C8 112.16(12) . . ? C9 N4 Cu1 107.65(9) . . ? C8 N4 Cu1 117.34(10) . . ? C9 N4 H4 106.3 . . ? C8 N4 H4 106.3 . . ? Cu1 N4 H4 106.3 . . ? O3 N5 O2 120.23(15) . . ? O3 N5 O1 119.89(13) . . ? O2 N5 O1 119.86(15) . . ? O5 N6 O6 120.93(14) . . ? O5 N6 O4 119.16(14) . . ? O6 N6 O4 119.91(13) . . ? N1 C1 C2 114.89(12) . . ? N1 C1 H1A 108.5 . . ? C2 C1 H1A 108.5 . . ? N1 C1 H1B 108.5 . . ? C2 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? C1 C2 C3 114.56(13) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? N2 C3 C2 114.93(12) . . ? N2 C3 H3A 108.5 . . ? C2 C3 H3A 108.5 . . ? N2 C3 H3B 108.5 . . ? C2 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? N2 C4 C5 110.31(13) . . ? N2 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? N2 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? N3 C5 C4 107.56(13) . . ? N3 C5 H5A 110.2 . . ? C4 C5 H5A 110.2 . . ? N3 C5 H5B 110.2 . . ? C4 C5 H5B 110.2 . . ? H5A C5 H5B 108.5 . . ? N3 C6 C7 111.33(13) . . ? N3 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C6 C7 C8 114.72(13) . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? N4 C8 C7 111.02(13) . . ? N4 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? N4 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N4 C9 C10 107.21(12) . . ? N4 C9 H9A 110.3 . . ? C10 C9 H9A 110.3 . . ? N4 C9 H9B 110.3 . . ? C10 C9 H9B 110.3 . . ? H9A C9 H9B 108.5 . . ? N1 C10 C9 109.91(12) . . ? N1 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? N1 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? N1 C11 C12 117.35(11) . . ? N1 C11 H11A 108.0 . . ? C12 C11 H11A 108.0 . . ? N1 C11 H11B 108.0 . . ? C12 C11 H11B 108.0 . . ? H11A C11 H11B 107.2 . . ? C17 C12 C13 118.81(14) . . ? C17 C12 C11 120.88(13) . . ? C13 C12 C11 120.02(13) . . ? C14 C13 C12 120.67(16) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 120.07(16) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 119.88(15) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C17 120.25(16) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 120.31(15) . . ? C12 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? N2 C18 C19 116.98(12) . . ? N2 C18 H18A 108.1 . . ? C19 C18 H18A 108.1 . . ? N2 C18 H18B 108.1 . . ? C19 C18 H18B 108.1 . . ? H18A C18 H18B 107.3 . . ? C24 C19 C20 118.71(15) . . ? C24 C19 C18 121.11(15) . . ? C20 C19 C18 120.01(15) . . ? C21 C20 C19 120.48(19) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C22 C21 C20 120.3(2) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C23 C22 C21 119.80(17) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 120.5(2) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C19 C24 C23 120.20(19) . . ? C19 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? O7 C25 H25A 109.5 . . ? O7 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O7 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 O1 N5 -122.29(16) . . . . ? N4 Cu1 O1 N5 -31.78(16) . . . . ? N1 Cu1 O1 N5 54.81(16) . . . . ? N2 Cu1 O1 N5 151.79(16) . . . . ? O4 Cu1 O1 N5 -119.3(2) . . . . ? N3 Cu1 O4 N6 66.28(10) . . . . ? N4 Cu1 O4 N6 -24.34(10) . . . . ? N1 Cu1 O4 N6 -110.87(10) . . . . ? N2 Cu1 O4 N6 152.67(10) . . . . ? O1 Cu1 O4 N6 63.3(3) . . . . ? N3 Cu1 N1 C1 -87.8(7) . . . . ? N4 Cu1 N1 C1 -135.89(10) . . . . ? N2 Cu1 N1 C1 40.41(10) . . . . ? O4 Cu1 N1 C1 -46.88(9) . . . . ? O1 Cu1 N1 C1 134.09(9) . . . . ? N3 Cu1 N1 C10 28.8(7) . . . . ? N4 Cu1 N1 C10 -19.34(9) . . . . ? N2 Cu1 N1 C10 156.96(8) . . . . ? O4 Cu1 N1 C10 69.66(8) . . . . ? O1 Cu1 N1 C10 -109.36(8) . . . . ? N3 Cu1 N1 C11 146.5(6) . . . . ? N4 Cu1 N1 C11 98.36(9) . . . . ? N2 Cu1 N1 C11 -85.34(9) . . . . ? O4 Cu1 N1 C11 -172.63(9) . . . . ? O1 Cu1 N1 C11 8.34(9) . . . . ? N3 Cu1 N2 C3 135.48(10) . . . . ? N4 Cu1 N2 C3 88.4(6) . . . . ? N1 Cu1 N2 C3 -41.10(10) . . . . ? O4 Cu1 N2 C3 49.74(9) . . . . ? O1 Cu1 N2 C3 -139.85(9) . . . . ? N3 Cu1 N2 C4 19.04(9) . . . . ? N4 Cu1 N2 C4 -28.0(6) . . . . ? N1 Cu1 N2 C4 -157.54(9) . . . . ? O4 Cu1 N2 C4 -66.70(9) . . . . ? O1 Cu1 N2 C4 103.71(9) . . . . ? N3 Cu1 N2 C18 -99.15(10) . . . . ? N4 Cu1 N2 C18 -146.2(6) . . . . ? N1 Cu1 N2 C18 84.27(9) . . . . ? O4 Cu1 N2 C18 175.10(9) . . . . ? O1 Cu1 N2 C18 -14.48(9) . . . . ? N4 Cu1 N3 C5 -174.46(10) . . . . ? N1 Cu1 N3 C5 137.5(6) . . . . ? N2 Cu1 N3 C5 9.04(10) . . . . ? O4 Cu1 N3 C5 96.51(10) . . . . ? O1 Cu1 N3 C5 -83.99(10) . . . . ? N4 Cu1 N3 C6 -44.61(11) . . . . ? N1 Cu1 N3 C6 -92.6(7) . . . . ? N2 Cu1 N3 C6 138.89(11) . . . . ? O4 Cu1 N3 C6 -133.64(11) . . . . ? O1 Cu1 N3 C6 45.86(11) . . . . ? N3 Cu1 N4 C9 173.27(10) . . . . ? N1 Cu1 N4 C9 -9.95(9) . . . . ? N2 Cu1 N4 C9 -139.8(6) . . . . ? O4 Cu1 N4 C9 -101.16(9) . . . . ? O1 Cu1 N4 C9 88.41(9) . . . . ? N3 Cu1 N4 C8 45.67(11) . . . . ? N1 Cu1 N4 C8 -137.55(11) . . . . ? N2 Cu1 N4 C8 92.6(6) . . . . ? O4 Cu1 N4 C8 131.24(11) . . . . ? O1 Cu1 N4 C8 -39.19(11) . . . . ? Cu1 O1 N5 O3 -19.7(2) . . . . ? Cu1 O1 N5 O2 161.64(14) . . . . ? Cu1 O4 N6 O5 121.29(14) . . . . ? Cu1 O4 N6 O6 -57.98(16) . . . . ? C10 N1 C1 C2 -168.66(12) . . . . ? C11 N1 C1 C2 68.46(15) . . . . ? Cu1 N1 C1 C2 -55.93(14) . . . . ? N1 C1 C2 C3 67.88(17) . . . . ? C4 N2 C3 C2 171.38(12) . . . . ? C18 N2 C3 C2 -66.47(15) . . . . ? Cu1 N2 C3 C2 58.02(14) . . . . ? C1 C2 C3 N2 -69.49(16) . . . . ? C3 N2 C4 C5 -163.55(12) . . . . ? C18 N2 C4 C5 73.56(15) . . . . ? Cu1 N2 C4 C5 -44.35(13) . . . . ? C6 N3 C5 C4 -168.37(13) . . . . ? Cu1 N3 C5 C4 -35.27(14) . . . . ? N2 C4 C5 N3 54.76(16) . . . . ? C5 N3 C6 C7 -172.90(13) . . . . ? Cu1 N3 C6 C7 58.85(16) . . . . ? N3 C6 C7 C8 -66.04(19) . . . . ? C9 N4 C8 C7 173.40(12) . . . . ? Cu1 N4 C8 C7 -61.21(15) . . . . ? C6 C7 C8 N4 67.67(18) . . . . ? C8 N4 C9 C10 167.99(12) . . . . ? Cu1 N4 C9 C10 37.45(13) . . . . ? C1 N1 C10 C9 166.04(12) . . . . ? C11 N1 C10 C9 -70.48(14) . . . . ? Cu1 N1 C10 C9 46.11(12) . . . . ? N4 C9 C10 N1 -58.00(15) . . . . ? C1 N1 C11 C12 73.00(15) . . . . ? C10 N1 C11 C12 -48.47(16) . . . . ? Cu1 N1 C11 C12 -160.49(10) . . . . ? N1 C11 C12 C17 -91.04(17) . . . . ? N1 C11 C12 C13 95.24(16) . . . . ? C17 C12 C13 C14 0.8(2) . . . . ? C11 C12 C13 C14 174.67(14) . . . . ? C12 C13 C14 C15 -1.6(3) . . . . ? C13 C14 C15 C16 1.0(3) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? C13 C12 C17 C16 0.5(2) . . . . ? C11 C12 C17 C16 -173.32(14) . . . . ? C15 C16 C17 C12 -1.1(3) . . . . ? C3 N2 C18 C19 -63.57(16) . . . . ? C4 N2 C18 C19 57.26(17) . . . . ? Cu1 N2 C18 C19 170.82(11) . . . . ? N2 C18 C19 C24 87.53(18) . . . . ? N2 C18 C19 C20 -97.24(17) . . . . ? C24 C19 C20 C21 -0.6(2) . . . . ? C18 C19 C20 C21 -175.93(15) . . . . ? C19 C20 C21 C22 0.9(3) . . . . ? C20 C21 C22 C23 -0.5(3) . . . . ? C21 C22 C23 C24 -0.3(3) . . . . ? C20 C19 C24 C23 -0.2(2) . . . . ? C18 C19 C24 C23 175.08(15) . . . . ? C22 C23 C24 C19 0.7(3) . . . . ? 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 O7 H7 O1 0.84 2.16 2.867(2) 142.2 . O7 H7 O2 0.84 2.29 3.053(3) 151.3 . O7 H7 N5 0.84 2.57 3.382(2) 163.9 . N3 H3 O6 0.93 2.19 3.0188(19) 148.3 . N4 H4 O5 0.93 2.29 2.9348(18) 125.5 3_565 N4 H4 N6 0.93 2.49 3.2217(19) 135.2 . N4 H4 O6 0.93 2.53 3.2671(19) 136.7 . _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 1.077 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.055 #===END data_lfl56 _database_code_CSD 198033 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H36 Cl2 N4 Ni O8' _chemical_formula_weight 638.18 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' Cl Cl 0.1484 0.1585 '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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0053(10) _cell_length_b 17.8845(19) _cell_length_c 8.6964(9) _cell_angle_alpha 90.00 _cell_angle_beta 104.909(2) _cell_angle_gamma 90.00 _cell_volume 1353.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 985 _cell_measurement_theta_min 2.678 _cell_measurement_theta_max 28.170 _exptl_crystal_description primatic _exptl_crystal_colour orange _exptl_crystal_size_max 0.352 _exptl_crystal_size_mid 0.337 _exptl_crystal_size_min 0.206 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 0.970 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_correction_T_min 0.698 _exptl_absorpt_correction_T_max 0.834 _exptl_absorpt_process_details ; Gaussian (Coppens et al., 1965) XPREP (Bruker, 1995) ; _exptl_special_details ; ? ; _diffrn_crystal_treatment ; attached to a thin glass fibre ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 211 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.01 _diffrn_reflns_number 13290 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0106 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3219 _reflns_number_gt 2876 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; teXsan for Windows (MSC, 1997) xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3219 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.1008 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 1.202 _refine_ls_restrained_S_all 1.202 _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 Ni1 Ni 1.0000 0.5000 0.5000 0.02955(11) Uani 1 2 d S . . Cl1 Cl 0.84782(6) 0.63308(3) 0.82375(6) 0.04086(14) Uani 1 1 d . . . O1 O 0.6989(3) 0.6140(2) 0.8379(3) 0.1079(9) Uani 1 1 d . . . O2 O 0.8960(4) 0.69888(12) 0.9063(3) 0.1170(11) Uani 1 1 d . . . O3 O 0.8333(3) 0.63746(16) 0.6589(2) 0.0964(8) Uani 1 1 d . . . O4 O 0.9481(2) 0.57375(11) 0.8920(3) 0.0827(7) Uani 1 1 d . . . N1 N 0.84965(17) 0.42095(8) 0.50748(19) 0.0336(3) Uani 1 1 d . . . N2 N 0.85112(18) 0.55842(9) 0.34482(19) 0.0368(3) Uani 1 1 d . . . H2 H 0.7889 0.5800 0.3996 0.044 Uiso 1 1 calc R . . C1 C 0.7500(2) 0.39783(11) 0.3491(2) 0.0418(4) Uani 1 1 d . . . H1A H 0.6825 0.3580 0.3655 0.050 Uiso 1 1 calc R . . H1B H 0.8150 0.3775 0.2860 0.050 Uiso 1 1 calc R . . C2 C 0.6527(2) 0.45959(14) 0.2551(3) 0.0488(5) Uani 1 1 d . . . H2A H 0.5841 0.4383 0.1606 0.059 Uiso 1 1 calc R . . H2B H 0.5899 0.4813 0.3190 0.059 Uiso 1 1 calc R . . C3 C 0.7466(3) 0.52062(14) 0.2057(3) 0.0472(5) Uani 1 1 d . . . H3A H 0.8073 0.4993 0.1392 0.057 Uiso 1 1 calc R . . H3B H 0.6779 0.5574 0.1429 0.057 Uiso 1 1 calc R . . C4 C 0.9305(2) 0.62156(12) 0.2860(3) 0.0444(5) Uani 1 1 d . . . H4A H 0.9702 0.6051 0.1980 0.053 Uiso 1 1 calc R . . H4B H 0.8593 0.6624 0.2496 0.053 Uiso 1 1 calc R . . C5 C 1.0590(2) 0.64634(10) 0.4220(3) 0.0418(4) Uani 1 1 d . . . H5A H 1.0181 0.6710 0.5017 0.050 Uiso 1 1 calc R . . H5B H 1.1242 0.6815 0.3851 0.050 Uiso 1 1 calc R . . C6 C 0.7571(2) 0.45044(10) 0.6182(2) 0.0358(4) Uani 1 1 d . . . H6A H 0.8277 0.4737 0.7089 0.043 Uiso 1 1 calc R . . H6B H 0.6889 0.4893 0.5625 0.043 Uiso 1 1 calc R . . C7 C 0.6617(2) 0.39390(10) 0.6798(2) 0.0338(4) Uani 1 1 d . . . C8 C 0.7103(2) 0.36955(13) 0.8361(2) 0.0450(5) Uani 1 1 d . . . H8 H 0.8020 0.3876 0.9010 0.054 Uiso 1 1 calc R . . C9 C 0.6238(3) 0.31842(14) 0.8975(3) 0.0520(5) Uani 1 1 d . . . H9 H 0.6578 0.3028 1.0027 0.062 Uiso 1 1 calc R . . C10 C 0.4878(3) 0.29096(12) 0.8026(3) 0.0471(5) Uani 1 1 d . . . H10 H 0.4305 0.2565 0.8433 0.057 Uiso 1 1 calc R . . C11 C 0.4371(2) 0.31500(11) 0.6464(2) 0.0411(4) Uani 1 1 d . . . H11 H 0.3456 0.2965 0.5819 0.049 Uiso 1 1 calc R . . C12 C 0.5223(2) 0.36673(11) 0.5856(2) 0.0360(4) Uani 1 1 d . . . H12 H 0.4862 0.3834 0.4813 0.043 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 Ni1 0.02785(18) 0.02727(17) 0.03520(19) 0.00154(11) 0.01113(13) -0.00145(11) Cl1 0.0441(3) 0.0399(3) 0.0366(2) -0.00063(17) 0.00687(19) 0.00292(18) O1 0.0606(13) 0.161(3) 0.111(2) 0.0328(19) 0.0378(13) 0.0009(15) O2 0.166(3) 0.0458(11) 0.110(2) -0.0176(12) -0.0174(19) -0.0104(14) O3 0.1048(18) 0.143(2) 0.0415(10) 0.0119(12) 0.0186(11) -0.0137(16) O4 0.0761(13) 0.0633(12) 0.0859(14) -0.0161(10) -0.0208(11) 0.0281(10) N1 0.0335(7) 0.0288(7) 0.0417(8) -0.0022(6) 0.0155(6) -0.0029(6) N2 0.0342(8) 0.0362(8) 0.0418(8) 0.0043(6) 0.0131(7) 0.0024(6) C1 0.0439(10) 0.0394(10) 0.0453(10) -0.0110(8) 0.0173(8) -0.0098(8) C2 0.0389(10) 0.0570(13) 0.0474(11) -0.0073(10) 0.0055(9) -0.0072(9) C3 0.0449(11) 0.0540(12) 0.0404(11) 0.0046(9) 0.0066(9) 0.0018(10) C4 0.0416(10) 0.0410(10) 0.0538(12) 0.0141(9) 0.0183(9) 0.0039(8) C5 0.0429(10) 0.0296(9) 0.0586(12) 0.0037(8) 0.0235(9) 0.0004(8) C6 0.0358(9) 0.0321(8) 0.0430(10) -0.0061(7) 0.0165(8) -0.0040(7) C7 0.0324(8) 0.0346(9) 0.0374(9) -0.0038(7) 0.0144(7) -0.0015(7) C8 0.0397(10) 0.0568(12) 0.0374(10) -0.0022(9) 0.0080(8) -0.0054(9) C9 0.0558(13) 0.0611(14) 0.0394(11) 0.0108(10) 0.0129(9) -0.0022(11) C10 0.0499(12) 0.0443(11) 0.0522(12) 0.0074(9) 0.0223(10) -0.0055(9) C11 0.0351(9) 0.0428(10) 0.0474(11) -0.0029(8) 0.0141(8) -0.0066(8) C12 0.0333(9) 0.0398(10) 0.0359(9) -0.0004(7) 0.0108(7) -0.0015(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 Ni1 N2 1.9441(16) . ? Ni1 N2 1.9441(16) 3_766 ? Ni1 N1 1.9701(15) 3_766 ? Ni1 N1 1.9701(15) . ? Cl1 O2 1.388(2) . ? Cl1 O3 1.408(2) . ? Cl1 O1 1.419(2) . ? Cl1 O4 1.4204(19) . ? N1 C1 1.496(2) . ? N1 C5 1.497(2) 3_766 ? N1 C6 1.521(2) . ? N2 C3 1.490(3) . ? N2 C4 1.496(2) . ? N2 H2 0.9100 . ? C1 C2 1.513(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.509(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.494(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.497(2) 3_766 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.511(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.387(3) . ? C7 C12 1.398(3) . ? C8 C9 1.394(3) . ? C8 H8 0.9300 . ? C9 C10 1.379(3) . ? C9 H9 0.9300 . ? C10 C11 1.386(3) . ? C10 H10 0.9300 . ? C11 C12 1.390(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni1 N2 180.000(1) . 3_766 ? N2 Ni1 N1 87.05(7) . 3_766 ? N2 Ni1 N1 92.95(7) 3_766 3_766 ? N2 Ni1 N1 92.95(7) . . ? N2 Ni1 N1 87.05(7) 3_766 . ? N1 Ni1 N1 180.0 3_766 . ? O2 Cl1 O3 114.46(18) . . ? O2 Cl1 O1 109.6(2) . . ? O3 Cl1 O1 105.04(16) . . ? O2 Cl1 O4 109.68(15) . . ? O3 Cl1 O4 110.45(16) . . ? O1 Cl1 O4 107.29(17) . . ? C1 N1 C5 106.92(15) . 3_766 ? C1 N1 C6 112.45(14) . . ? C5 N1 C6 110.64(15) 3_766 . ? C1 N1 Ni1 115.00(12) . . ? C5 N1 Ni1 106.29(11) 3_766 . ? C6 N1 Ni1 105.39(10) . . ? C3 N2 C4 108.80(16) . . ? C3 N2 Ni1 119.89(13) . . ? C4 N2 Ni1 109.78(12) . . ? C3 N2 H2 105.8 . . ? C4 N2 H2 105.8 . . ? Ni1 N2 H2 105.8 . . ? N1 C1 C2 115.02(16) . . ? N1 C1 H1A 108.5 . . ? C2 C1 H1A 108.5 . . ? N1 C1 H1B 108.5 . . ? C2 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? C3 C2 C1 113.11(18) . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N2 C3 C2 112.35(17) . . ? N2 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? N2 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C5 C4 N2 107.09(16) . . ? C5 C4 H4A 110.3 . . ? N2 C4 H4A 110.3 . . ? C5 C4 H4B 110.3 . . ? N2 C4 H4B 110.3 . . ? H4A C4 H4B 108.6 . . ? C4 C5 N1 108.54(16) . 3_766 ? C4 C5 H5A 110.0 . . ? N1 C5 H5A 110.0 3_766 . ? C4 C5 H5B 110.0 . . ? N1 C5 H5B 110.0 3_766 . ? H5A C5 H5B 108.4 . . ? C7 C6 N1 116.53(15) . . ? C7 C6 H6A 108.2 . . ? N1 C6 H6A 108.2 . . ? C7 C6 H6B 108.2 . . ? N1 C6 H6B 108.2 . . ? H6A C6 H6B 107.3 . . ? C8 C7 C12 118.35(17) . . ? C8 C7 C6 119.52(17) . . ? C12 C7 C6 122.10(17) . . ? C7 C8 C9 121.0(2) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 120.2(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.61(19) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 120.28(19) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 120.59(18) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Ni1 N1 C1 43.58(13) . . . . ? N2 Ni1 N1 C1 -136.42(13) 3_766 . . . ? N1 Ni1 N1 C1 84(100) 3_766 . . . ? N2 Ni1 N1 C5 161.68(12) . . . 3_766 ? N2 Ni1 N1 C5 -18.32(12) 3_766 . . 3_766 ? N1 Ni1 N1 C5 -158(100) 3_766 . . 3_766 ? N2 Ni1 N1 C6 -80.85(12) . . . . ? N2 Ni1 N1 C6 99.15(12) 3_766 . . . ? N1 Ni1 N1 C6 -41(100) 3_766 . . . ? N2 Ni1 N2 C3 0(100) 3_766 . . . ? N1 Ni1 N2 C3 135.76(15) 3_766 . . . ? N1 Ni1 N2 C3 -44.24(15) . . . . ? N2 Ni1 N2 C4 0(100) 3_766 . . . ? N1 Ni1 N2 C4 8.76(13) 3_766 . . . ? N1 Ni1 N2 C4 -171.24(13) . . . . ? C5 N1 C1 C2 -177.54(16) 3_766 . . . ? C6 N1 C1 C2 60.8(2) . . . . ? Ni1 N1 C1 C2 -59.80(19) . . . . ? N1 C1 C2 C3 65.1(2) . . . . ? C4 N2 C3 C2 -175.71(18) . . . . ? Ni1 N2 C3 C2 56.8(2) . . . . ? C1 C2 C3 N2 -60.9(2) . . . . ? C3 N2 C4 C5 -167.03(16) . . . . ? Ni1 N2 C4 C5 -34.04(18) . . . . ? N2 C4 C5 N1 50.2(2) . . . 3_766 ? C1 N1 C6 C7 69.5(2) . . . . ? C5 N1 C6 C7 -50.0(2) 3_766 . . . ? Ni1 N1 C6 C7 -164.52(13) . . . . ? N1 C6 C7 C8 105.3(2) . . . . ? N1 C6 C7 C12 -76.8(2) . . . . ? C12 C7 C8 C9 0.9(3) . . . . ? C6 C7 C8 C9 178.9(2) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? C8 C9 C10 C11 -0.6(4) . . . . ? C9 C10 C11 C12 -0.3(3) . . . . ? C10 C11 C12 C7 1.4(3) . . . . ? C8 C7 C12 C11 -1.8(3) . . . . ? C6 C7 C12 C11 -179.69(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 N2 H2 O3 0.91 2.42 3.116(3) 133.9 . _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.670 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.058 #===END data_lfl19 _database_code_CSD 198034 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H36 Cu N6 O6' _chemical_formula_weight 568.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.9521(19) _cell_length_b 11.851(2) _cell_length_c 10.868(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.436(3) _cell_angle_gamma 90.00 _cell_volume 1271.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 855 _cell_measurement_theta_min 3.127 _cell_measurement_theta_max 28.115 _exptl_crystal_description tabular _exptl_crystal_colour purple _exptl_crystal_size_max 0.265 _exptl_crystal_size_mid 0.173 _exptl_crystal_size_min 0.088 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 598 _exptl_absorpt_coefficient_mu 0.911 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.794 _exptl_absorpt_correction_T_max 0.924 _exptl_absorpt_process_details 'Gaussian and SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 108 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.000 _diffrn_reflns_number 11469 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3008 _reflns_number_gt 2523 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'teXsan for Windows (MSC, 1997)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+0.4730P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3008 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0766 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.0000 0.5000 0.02739(9) Uani 1 2 d S . . N1 N 0.32550(14) 0.01204(10) 0.59049(13) 0.0294(3) Uani 1 1 d . . . N2 N 0.41382(13) 0.07702(11) 0.34716(12) 0.0311(3) Uani 1 1 d . . . H2N H 0.4074 0.1512 0.3674 0.037 Uiso 1 1 calc R . . C1 C 0.20026(17) -0.01516(14) 0.50467(17) 0.0355(4) Uani 1 1 d . . . H1A H 0.1230 -0.0086 0.5502 0.043 Uiso 1 1 calc R . . H1B H 0.2054 -0.0931 0.4785 0.043 Uiso 1 1 calc R . . C2 C 0.17534(16) 0.05886(16) 0.38955(16) 0.0391(4) Uani 1 1 d . . . H2A H 0.0845 0.0444 0.3485 0.047 Uiso 1 1 calc R . . H2B H 0.1793 0.1373 0.4152 0.047 Uiso 1 1 calc R . . C3 C 0.27502(17) 0.04090(16) 0.29685(16) 0.0380(4) Uani 1 1 d . . . H3A H 0.2763 -0.0384 0.2749 0.046 Uiso 1 1 calc R . . H3B H 0.2452 0.0833 0.2219 0.046 Uiso 1 1 calc R . . C4 C 0.49314(18) -0.07225(16) 0.74924(15) 0.0382(4) Uani 1 1 d . . . H4A H 0.5070 -0.0025 0.7958 0.046 Uiso 1 1 calc R . . H4B H 0.5114 -0.1348 0.8065 0.046 Uiso 1 1 calc R . . C5 C 0.34945(17) -0.07853(14) 0.68652(15) 0.0347(3) Uani 1 1 d . . . H5A H 0.3331 -0.1518 0.6478 0.042 Uiso 1 1 calc R . . H5B H 0.2873 -0.0692 0.7475 0.042 Uiso 1 1 calc R . . C6 C 0.31489(16) 0.12614(13) 0.65122(15) 0.0322(3) Uani 1 1 d . . . H6A H 0.3104 0.1838 0.5875 0.039 Uiso 1 1 calc R . . H6B H 0.3970 0.1390 0.7080 0.039 Uiso 1 1 calc R . . C7 C 0.19407(16) 0.14040(13) 0.72208(15) 0.0322(3) Uani 1 1 d . . . C8 C 0.19723(19) 0.10049(15) 0.84378(16) 0.0393(4) Uani 1 1 d . . . H8 H 0.2756 0.0670 0.8835 0.047 Uiso 1 1 calc R . . C9 C 0.0840(2) 0.11069(17) 0.90525(19) 0.0505(5) Uani 1 1 d . . . H9 H 0.0861 0.0814 0.9849 0.061 Uiso 1 1 calc R . . C10 C -0.0314(2) 0.16367(19) 0.8498(2) 0.0551(5) Uani 1 1 d . . . H10 H -0.1066 0.1704 0.8919 0.066 Uiso 1 1 calc R . . C11 C -0.03503(19) 0.20656(19) 0.7318(2) 0.0524(5) Uani 1 1 d . . . H11 H -0.1120 0.2439 0.6947 0.063 Uiso 1 1 calc R . . C12 C 0.07663(7) 0.19401(6) 0.66787(7) 0.0413(4) Uani 1 1 d . . . H12 H 0.0727 0.2219 0.5875 0.050 Uiso 1 1 calc R . . O1 O 0.59601(7) 0.20095(6) 0.57585(7) 0.0529(3) Uani 1 1 d R . . O2 O 0.49031(7) 0.30651(6) 0.43445(7) 0.0673(5) Uani 1 1 d R . . O3 O 0.69254(7) 0.34981(6) 0.51644(7) 0.0769(5) Uani 1 1 d R . . N3 N 0.59371(7) 0.28730(6) 0.50789(7) 0.0410(3) Uani 1 1 d 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 0.02224(14) 0.03606(16) 0.02486(14) 0.00261(10) 0.00676(9) 0.00032(10) N1 0.0268(6) 0.0312(7) 0.0319(7) 0.0000(5) 0.0096(5) -0.0022(5) N2 0.0300(6) 0.0338(7) 0.0303(6) 0.0018(5) 0.0072(5) 0.0001(5) C1 0.0254(8) 0.0401(9) 0.0420(9) -0.0069(7) 0.0087(6) -0.0041(6) C2 0.0278(8) 0.0476(10) 0.0413(9) -0.0040(8) 0.0020(7) 0.0025(7) C3 0.0337(8) 0.0462(9) 0.0326(8) -0.0010(7) -0.0007(6) 0.0009(7) C4 0.0418(9) 0.0445(9) 0.0304(7) 0.0088(7) 0.0127(7) 0.0052(7) C5 0.0377(8) 0.0327(8) 0.0371(8) 0.0036(6) 0.0177(7) -0.0002(6) C6 0.0321(8) 0.0311(7) 0.0351(8) -0.0015(6) 0.0105(6) -0.0034(6) C7 0.0327(8) 0.0296(7) 0.0357(8) -0.0053(6) 0.0096(6) -0.0022(6) C8 0.0443(9) 0.0387(9) 0.0364(8) -0.0046(7) 0.0108(7) -0.0006(7) C9 0.0632(13) 0.0495(11) 0.0439(10) -0.0104(8) 0.0258(9) -0.0118(9) C10 0.0430(10) 0.0634(13) 0.0643(13) -0.0278(11) 0.0271(9) -0.0129(9) C11 0.0336(9) 0.0572(12) 0.0659(13) -0.0244(10) 0.0045(9) 0.0046(8) C12 0.0417(9) 0.0415(9) 0.0409(9) -0.0067(7) 0.0062(7) 0.0045(8) O1 0.0556(8) 0.0557(8) 0.0487(8) -0.0010(6) 0.0111(6) 0.0078(7) O2 0.0687(10) 0.0508(9) 0.0751(11) -0.0026(8) -0.0184(8) 0.0099(7) O3 0.0655(10) 0.0850(12) 0.0850(12) -0.0191(10) 0.0283(9) -0.0337(9) N3 0.0391(8) 0.0428(8) 0.0430(8) -0.0137(6) 0.0131(6) -0.0009(6) _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 1.9898(13) . ? Cu1 N2 1.9898(13) 3_656 ? Cu1 N1 2.1085(13) 3_656 ? Cu1 N1 2.1085(13) . ? Cu1 O1 2.6571 . ? N1 C1 1.492(2) . ? N1 C5 1.495(2) . ? N1 C6 1.514(2) . ? N2 C3 1.482(2) . ? N2 C4 1.486(2) 3_656 ? N2 H2N 0.9100 . ? C1 C2 1.522(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.518(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N2 1.486(2) 3_656 ? C4 C5 1.504(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.519(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C12 1.3923(18) . ? C7 C8 1.401(2) . ? C8 C9 1.388(3) . ? C8 H8 0.9300 . ? C9 C10 1.378(3) . ? C9 H9 0.9300 . ? C10 C11 1.375(3) . ? C10 H10 0.9300 . ? C11 C12 1.393(2) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? O1 N3 1.2605 . ? O2 N3 1.2391 . ? O3 N3 1.2252 . ? 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 N2 180.0 . 3_656 ? N2 Cu1 N1 86.20(5) . 3_656 ? N2 Cu1 N1 93.80(5) 3_656 3_656 ? N2 Cu1 N1 93.80(5) . . ? N2 Cu1 N1 86.20(5) 3_656 . ? N1 Cu1 N1 180.0 3_656 . ? N2 Cu1 O1 86.94(4) . . ? N2 Cu1 O1 93.06(4) 3_656 . ? N1 Cu1 O1 85.44(4) 3_656 . ? N1 Cu1 O1 94.56(4) . . ? C1 N1 C5 109.04(12) . . ? C1 N1 C6 111.45(12) . . ? C5 N1 C6 110.53(12) . . ? C1 N1 Cu1 111.44(10) . . ? C5 N1 Cu1 102.15(9) . . ? C6 N1 Cu1 111.83(9) . . ? C3 N2 C4 111.41(13) . 3_656 ? C3 N2 Cu1 117.14(10) . . ? C4 N2 Cu1 109.30(10) 3_656 . ? C3 N2 H2N 106.1 . . ? C4 N2 H2N 106.1 3_656 . ? Cu1 N2 H2N 106.1 . . ? N1 C1 C2 115.05(13) . . ? N1 C1 H1A 108.5 . . ? C2 C1 H1A 108.5 . . ? N1 C1 H1B 108.5 . . ? C2 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? C3 C2 C1 114.45(14) . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? N2 C3 C2 111.89(14) . . ? N2 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? N2 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N2 C4 C5 108.73(13) 3_656 . ? N2 C4 H4A 109.9 3_656 . ? C5 C4 H4A 109.9 . . ? N2 C4 H4B 109.9 3_656 . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? N1 C5 C4 109.71(13) . . ? N1 C5 H5A 109.7 . . ? C4 C5 H5A 109.7 . . ? N1 C5 H5B 109.7 . . ? C4 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? N1 C6 C7 115.14(12) . . ? N1 C6 H6A 108.5 . . ? C7 C6 H6A 108.5 . . ? N1 C6 H6B 108.5 . . ? C7 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C12 C7 C8 117.94(14) . . ? C12 C7 C6 120.83(13) . . ? C8 C7 C6 121.23(15) . . ? C9 C8 C7 120.30(18) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 120.81(19) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C11 C10 C9 119.74(18) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 119.96(18) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C7 C12 C11 121.19(13) . . ? C7 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? N3 O1 Cu1 124.6 . . ? O3 N3 O2 122.0 . . ? O3 N3 O1 119.5 . . ? O2 N3 O1 118.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 N1 C1 42.76(10) . . . . ? N2 Cu1 N1 C1 -137.24(10) 3_656 . . . ? N1 Cu1 N1 C1 142(100) 3_656 . . . ? O1 Cu1 N1 C1 129.99(10) . . . . ? N2 Cu1 N1 C5 159.06(10) . . . . ? N2 Cu1 N1 C5 -20.94(10) 3_656 . . . ? N1 Cu1 N1 C5 -102(100) 3_656 . . . ? O1 Cu1 N1 C5 -113.71(9) . . . . ? N2 Cu1 N1 C6 -82.73(11) . . . . ? N2 Cu1 N1 C6 97.27(11) 3_656 . . . ? N1 Cu1 N1 C6 16(100) 3_656 . . . ? O1 Cu1 N1 C6 4.50(10) . . . . ? N2 Cu1 N2 C3 -129(100) 3_656 . . . ? N1 Cu1 N2 C3 134.60(12) 3_656 . . . ? N1 Cu1 N2 C3 -45.40(12) . . . . ? O1 Cu1 N2 C3 -139.77(11) . . . . ? N2 Cu1 N2 C4 103(100) 3_656 . . 3_656 ? N1 Cu1 N2 C4 6.72(11) 3_656 . . 3_656 ? N1 Cu1 N2 C4 -173.28(11) . . . 3_656 ? O1 Cu1 N2 C4 92.35(11) . . . 3_656 ? C5 N1 C1 C2 -170.33(13) . . . . ? C6 N1 C1 C2 67.38(17) . . . . ? Cu1 N1 C1 C2 -58.32(15) . . . . ? N1 C1 C2 C3 69.05(19) . . . . ? C4 N2 C3 C2 -173.05(14) 3_656 . . . ? Cu1 N2 C3 C2 60.09(17) . . . . ? C1 C2 C3 N2 -66.5(2) . . . . ? C1 N1 C5 C4 163.24(13) . . . . ? C6 N1 C5 C4 -73.92(16) . . . . ? Cu1 N1 C5 C4 45.21(14) . . . . ? N2 C4 C5 N1 -54.67(17) 3_656 . . . ? C1 N1 C6 C7 56.39(18) . . . . ? C5 N1 C6 C7 -65.03(17) . . . . ? Cu1 N1 C6 C7 -178.12(11) . . . . ? N1 C6 C7 C12 -97.94(16) . . . . ? N1 C6 C7 C8 82.24(19) . . . . ? C12 C7 C8 C9 2.5(2) . . . . ? C6 C7 C8 C9 -177.63(16) . . . . ? C7 C8 C9 C10 -2.4(3) . . . . ? C8 C9 C10 C11 0.3(3) . . . . ? C9 C10 C11 C12 1.5(3) . . . . ? C8 C7 C12 C11 -0.7(2) . . . . ? C6 C7 C12 C11 179.44(14) . . . . ? C10 C11 C12 C7 -1.3(2) . . . . ? N2 Cu1 O1 N3 -11.95(4) . . . . ? N2 Cu1 O1 N3 168.05(4) 3_656 . . . ? N1 Cu1 O1 N3 74.47(4) 3_656 . . . ? N1 Cu1 O1 N3 -105.53(4) . . . . ? Cu1 O1 N3 O3 -138.8 . . . . ? Cu1 O1 N3 O2 41.6 . . . . ? 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 N2 H2N O2 0.91 2.11 2.9478(16) 152.9 . _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.317 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.049 #===END data_lfl27 _database_code_CSD 198035 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H58 Cu N6 O9' _chemical_formula_weight 830.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_Int_Tables_number 15 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' '-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 24.200(12) _cell_length_b 9.471(5) _cell_length_c 18.229(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.129(9) _cell_angle_gamma 90.00 _cell_volume 4113(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 935 _cell_measurement_theta_min 3.421 _cell_measurement_theta_max 27.546 _exptl_crystal_description prismatc _exptl_crystal_colour blue _exptl_crystal_size_max 0.216 _exptl_crystal_size_mid 0.183 _exptl_crystal_size_min 0.117 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1764 _exptl_absorpt_coefficient_mu 0.592 _exptl_absorpt_correction_type 'numerical and empirical' _exptl_absorpt_correction_T_min 0.863 _exptl_absorpt_correction_T_max 0.936 _exptl_absorpt_process_details ; Gaussian (XPREP, Bruker 1995) and SADABS (Sheldrick, 1996) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 212 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.15 _diffrn_reflns_number 21311 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4881 _reflns_number_gt 4183 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'teXsan for Windows (MSC, 1997)' _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^)+(0.0936P)^2^+3.6807P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4881 _refine_ls_number_parameters 260 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1420 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.23864(3) 0.2500 0.01935(12) Uani 1 2 d S . . O1 O 0.5000 0.4736(2) 0.2500 0.0251(4) Uani 1 2 d SD . . H1O H 0.4733(9) 0.524(3) 0.2327(15) 0.034(7) Uiso 1 1 d D . . N1 N 0.53124(7) 0.23286(16) 0.36759(9) 0.0216(3) Uani 1 1 d . . . N2 N 0.41872(6) 0.18311(17) 0.26192(9) 0.0220(3) Uani 1 1 d . . . N3 N 0.40301(10) 0.7090(2) 0.14135(13) 0.0414(5) Uani 1 1 d . . . C1 C 0.51163(8) 0.0990(2) 0.39893(11) 0.0246(4) Uani 1 1 d . . . H1A H 0.5296 0.0913 0.4519 0.029 Uiso 1 1 calc R . . H1B H 0.5246 0.0179 0.3721 0.029 Uiso 1 1 calc R . . C2 C 0.44847(9) 0.0880(2) 0.39387(11) 0.0262(4) Uani 1 1 d . . . H2A H 0.4347 0.1760 0.4138 0.031 Uiso 1 1 calc R . . H2B H 0.4402 0.0092 0.4259 0.031 Uiso 1 1 calc R . . C3 C 0.41648(9) 0.0642(2) 0.31537(11) 0.0262(4) Uani 1 1 d . . . H3A H 0.4316 -0.0217 0.2950 0.031 Uiso 1 1 calc R . . H3B H 0.3767 0.0455 0.3183 0.031 Uiso 1 1 calc R . . C4 C 0.39105(8) 0.1318(2) 0.18716(11) 0.0248(4) Uani 1 1 d . . . H4A H 0.3498 0.1315 0.1842 0.030 Uiso 1 1 calc R . . H4B H 0.4032 0.0338 0.1796 0.030 Uiso 1 1 calc R . . C5 C 0.40642(8) 0.2263(2) 0.12706(12) 0.0246(4) Uani 1 1 d . . . H5A H 0.3891 0.1895 0.0775 0.030 Uiso 1 1 calc R . . H5B H 0.3916 0.3225 0.1324 0.030 Uiso 1 1 calc R . . C6 C 0.51859(8) 0.3593(2) 0.41301(11) 0.0234(4) Uani 1 1 d . . . H6A H 0.5295 0.4461 0.3889 0.028 Uiso 1 1 calc R . . H6B H 0.4776 0.3635 0.4118 0.028 Uiso 1 1 calc R . . C7 C 0.54793(8) 0.3584(2) 0.49357(11) 0.0249(4) Uani 1 1 d . . . C8 C 0.60070(9) 0.4203(2) 0.51374(12) 0.0329(5) Uani 1 1 d . . . H8 H 0.6180 0.4646 0.4769 0.040 Uiso 1 1 calc R . . C9 C 0.62817(11) 0.4175(3) 0.58746(14) 0.0423(6) Uani 1 1 d . . . H9 H 0.6645 0.4577 0.6005 0.051 Uiso 1 1 calc R . . C10 C 0.60253(12) 0.3559(3) 0.64211(13) 0.0433(6) Uani 1 1 d . . . H10 H 0.6214 0.3538 0.6924 0.052 Uiso 1 1 calc R . . C11 C 0.54985(12) 0.2982(3) 0.62329(12) 0.0383(5) Uani 1 1 d . . . H11 H 0.5321 0.2578 0.6608 0.046 Uiso 1 1 calc R . . C12 C 0.52238(10) 0.2988(2) 0.54927(12) 0.0299(4) Uani 1 1 d . . . H12 H 0.4860 0.2584 0.5366 0.036 Uiso 1 1 calc R . . C13 C 0.38969(8) 0.3140(2) 0.28380(11) 0.0243(4) Uani 1 1 d . . . H13A H 0.3969 0.3918 0.2505 0.029 Uiso 1 1 calc R . . H13B H 0.4076 0.3403 0.3350 0.029 Uiso 1 1 calc R . . C14 C 0.32700(8) 0.3056(2) 0.28175(12) 0.0276(4) Uani 1 1 d . . . C15 C 0.30440(11) 0.2536(2) 0.34131(15) 0.0360(5) Uani 1 1 d . . . H15 H 0.3285 0.2150 0.3833 0.043 Uiso 1 1 calc R . . C16 C 0.24653(12) 0.2575(3) 0.33988(18) 0.0445(6) Uani 1 1 d . . . H16 H 0.2314 0.2213 0.3808 0.053 Uiso 1 1 calc R . . C17 C 0.21116(10) 0.3139(3) 0.27920(17) 0.0471(6) Uani 1 1 d . . . H17 H 0.1718 0.3172 0.2785 0.057 Uiso 1 1 calc R . . C18 C 0.23306(11) 0.3651(4) 0.21987(17) 0.0529(7) Uani 1 1 d . . . H18 H 0.2087 0.4027 0.1778 0.064 Uiso 1 1 calc R . . C19 C 0.29061(10) 0.3622(3) 0.22104(15) 0.0414(6) Uani 1 1 d . . . H19 H 0.3053 0.3991 0.1800 0.050 Uiso 1 1 calc R . . O2 O 0.40184(8) 0.58594(19) 0.16369(10) 0.0441(4) Uani 1 1 d . . . O3 O 0.43302(13) 0.7960(3) 0.18031(17) 0.0756(8) Uani 1 1 d . . . O4 O 0.37431(15) 0.7429(3) 0.08080(16) 0.0961(12) Uani 1 1 d . . . O5 O 0.34311(15) 0.9859(3) -0.00162(19) 0.0919(9) Uani 1 1 d . . . H5O H 0.3506 0.9083 0.0202 0.138 Uiso 1 1 calc R . . C20 C 0.2871(2) 1.0275(6) 0.0045(3) 0.0982(15) Uani 1 1 d . . . H20A H 0.2605 0.9550 -0.0180 0.147 Uiso 1 1 calc R . . H20B H 0.2781 1.1174 -0.0215 0.147 Uiso 1 1 calc R . . H20C H 0.2843 1.0387 0.0572 0.147 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 0.02089(18) 0.02232(18) 0.01512(18) 0.000 0.00396(12) 0.000 O1 0.0302(10) 0.0238(10) 0.0207(10) 0.000 0.0026(8) 0.000 N1 0.0261(8) 0.0222(8) 0.0164(8) -0.0010(6) 0.0040(6) 0.0019(6) N2 0.0241(7) 0.0242(8) 0.0177(8) 0.0000(6) 0.0040(6) -0.0018(6) N3 0.0535(13) 0.0372(11) 0.0398(12) 0.0105(9) 0.0255(10) 0.0205(10) C1 0.0329(10) 0.0228(9) 0.0183(9) 0.0023(7) 0.0053(7) 0.0028(7) C2 0.0353(10) 0.0250(9) 0.0194(9) 0.0033(7) 0.0075(7) -0.0015(7) C3 0.0319(10) 0.0240(9) 0.0234(10) 0.0026(7) 0.0070(8) -0.0045(7) C4 0.0257(9) 0.0284(9) 0.0203(9) -0.0018(7) 0.0039(7) -0.0051(7) C5 0.0238(9) 0.0299(9) 0.0195(9) 0.0005(7) 0.0018(7) -0.0030(7) C6 0.0291(9) 0.0243(9) 0.0168(9) -0.0018(7) 0.0040(7) 0.0025(7) C7 0.0320(10) 0.0246(9) 0.0178(9) -0.0023(7) 0.0037(7) 0.0056(7) C8 0.0349(11) 0.0382(11) 0.0252(11) -0.0082(9) 0.0040(8) 0.0010(9) C9 0.0401(12) 0.0499(14) 0.0324(13) -0.0177(11) -0.0055(10) 0.0069(10) C10 0.0632(16) 0.0422(13) 0.0198(11) -0.0072(9) -0.0059(10) 0.0208(11) C11 0.0675(16) 0.0293(11) 0.0191(10) 0.0014(8) 0.0103(10) 0.0138(11) C12 0.0421(11) 0.0257(9) 0.0233(10) -0.0014(8) 0.0095(8) 0.0047(8) C13 0.0234(9) 0.0259(9) 0.0243(10) 0.0005(7) 0.0062(7) -0.0005(7) C14 0.0251(9) 0.0301(10) 0.0284(11) -0.0030(8) 0.0065(8) -0.0012(8) C15 0.0327(12) 0.0432(13) 0.0345(13) 0.0033(9) 0.0129(10) 0.0011(9) C16 0.0381(13) 0.0483(15) 0.0529(17) 0.0006(11) 0.0244(12) -0.0032(10) C17 0.0262(11) 0.0561(16) 0.0612(18) -0.0101(13) 0.0133(11) -0.0005(10) C18 0.0294(12) 0.076(2) 0.0520(17) 0.0037(14) 0.0040(11) 0.0125(12) C19 0.0310(11) 0.0568(15) 0.0369(13) 0.0072(11) 0.0073(9) 0.0089(10) O2 0.0573(11) 0.0336(9) 0.0433(10) 0.0036(7) 0.0142(8) 0.0078(8) O3 0.0950(19) 0.0426(12) 0.103(2) -0.0106(13) 0.0565(16) -0.0058(13) O4 0.110(2) 0.130(3) 0.0564(16) 0.0524(16) 0.0352(15) 0.0806(19) O5 0.116(3) 0.0757(19) 0.085(2) 0.0070(16) 0.0202(18) -0.0019(17) C20 0.101(4) 0.098(3) 0.083(3) -0.003(3) -0.018(3) -0.009(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 2.0841(18) . ? Cu1 N2 2.0841(18) 2_655 ? Cu1 N1 2.145(2) . ? Cu1 N1 2.145(2) 2_655 ? Cu1 O1 2.226(2) . ? O1 H1O 0.820(16) . ? N1 C5 1.496(3) 2_655 ? N1 C1 1.502(2) . ? N1 C6 1.517(2) . ? N2 C4 1.490(2) . ? N2 C3 1.497(2) . ? N2 C13 1.512(3) . ? N3 O2 1.236(3) . ? N3 O3 1.237(4) . ? N3 O4 1.239(4) . ? C1 C2 1.519(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.519(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.511(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N1 1.496(3) 2_655 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.515(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.395(3) . ? C7 C12 1.397(3) . ? C8 C9 1.391(3) . ? C8 H8 0.9500 . ? C9 C10 1.391(4) . ? C9 H9 0.9500 . ? C10 C11 1.374(4) . ? C10 H10 0.9500 . ? C11 C12 1.395(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.513(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.389(3) . ? C14 C19 1.395(3) . ? C15 C16 1.397(4) . ? C15 H15 0.9500 . ? C16 C17 1.381(4) . ? C16 H16 0.9500 . ? C17 C18 1.374(4) . ? C17 H17 0.9500 . ? C18 C19 1.390(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? O5 C20 1.436(6) . ? O5 H5O 0.8400 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 N2 150.76(9) . 2_655 ? N2 Cu1 N1 93.59(7) . . ? N2 Cu1 N1 85.67(6) 2_655 . ? N2 Cu1 N1 85.67(6) . 2_655 ? N2 Cu1 N1 93.59(7) 2_655 2_655 ? N1 Cu1 N1 177.08(8) . 2_655 ? N2 Cu1 O1 104.62(5) . . ? N2 Cu1 O1 104.62(5) 2_655 . ? N1 Cu1 O1 91.46(4) . . ? N1 Cu1 O1 91.46(4) 2_655 . ? Cu1 O1 H1O 125.6(19) . . ? C5 N1 C1 108.82(15) 2_655 . ? C5 N1 C6 107.17(15) 2_655 . ? C1 N1 C6 110.55(15) . . ? C5 N1 Cu1 103.92(12) 2_655 . ? C1 N1 Cu1 108.81(12) . . ? C6 N1 Cu1 117.12(12) . . ? C4 N2 C3 106.73(15) . . ? C4 N2 C13 110.72(15) . . ? C3 N2 C13 111.93(15) . . ? C4 N2 Cu1 105.52(11) . . ? C3 N2 Cu1 113.62(12) . . ? C13 N2 Cu1 108.15(12) . . ? O2 N3 O3 118.9(3) . . ? O2 N3 O4 119.8(3) . . ? O3 N3 O4 121.3(3) . . ? N1 C1 C2 114.62(16) . . ? N1 C1 H1A 108.6 . . ? C2 C1 H1A 108.6 . . ? N1 C1 H1B 108.6 . . ? C2 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? C1 C2 C3 114.08(16) . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? N2 C3 C2 115.50(16) . . ? N2 C3 H3A 108.4 . . ? C2 C3 H3A 108.4 . . ? N2 C3 H3B 108.4 . . ? C2 C3 H3B 108.4 . . ? H3A C3 H3B 107.5 . . ? N2 C4 C5 109.96(16) . . ? N2 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? N2 C4 H4B 109.7 . . ? C5 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? N1 C5 C4 110.56(16) 2_655 . ? N1 C5 H5A 109.5 2_655 . ? C4 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 2_655 . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C7 C6 N1 114.80(15) . . ? C7 C6 H6A 108.6 . . ? N1 C6 H6A 108.6 . . ? C7 C6 H6B 108.6 . . ? N1 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? C8 C7 C12 118.68(19) . . ? C8 C7 C6 120.31(18) . . ? C12 C7 C6 121.00(19) . . ? C9 C8 C7 120.4(2) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.2(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 119.9(2) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 120.2(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 120.5(2) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? N2 C13 C14 117.44(16) . . ? N2 C13 H13A 107.9 . . ? C14 C13 H13A 107.9 . . ? N2 C13 H13B 107.9 . . ? C14 C13 H13B 107.9 . . ? H13A C13 H13B 107.2 . . ? C15 C14 C19 118.4(2) . . ? C15 C14 C13 122.0(2) . . ? C19 C14 C13 119.3(2) . . ? C14 C15 C16 120.5(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 120.2(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 119.8(2) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C19 120.3(3) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C14 120.7(2) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? C20 O5 H5O 109.5 . . ? O5 C20 H20A 109.5 . . ? O5 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O5 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 N1 C5 163.16(11) . . . 2_655 ? N2 Cu1 N1 C5 12.46(11) 2_655 . . 2_655 ? N1 Cu1 N1 C5 87.91(11) 2_655 . . 2_655 ? O1 Cu1 N1 C5 -92.09(11) . . . 2_655 ? N2 Cu1 N1 C1 47.34(12) . . . . ? N2 Cu1 N1 C1 -103.36(12) 2_655 . . . ? N1 Cu1 N1 C1 -27.91(11) 2_655 . . . ? O1 Cu1 N1 C1 152.09(11) . . . . ? N2 Cu1 N1 C6 -78.90(14) . . . . ? N2 Cu1 N1 C6 130.40(14) 2_655 . . . ? N1 Cu1 N1 C6 -154.15(13) 2_655 . . . ? O1 Cu1 N1 C6 25.85(13) . . . . ? N2 Cu1 N2 C4 -73.88(11) 2_655 . . . ? N1 Cu1 N2 C4 -161.43(12) . . . . ? N1 Cu1 N2 C4 15.73(12) 2_655 . . . ? O1 Cu1 N2 C4 106.12(11) . . . . ? N2 Cu1 N2 C3 42.70(12) 2_655 . . . ? N1 Cu1 N2 C3 -44.85(13) . . . . ? N1 Cu1 N2 C3 132.32(13) 2_655 . . . ? O1 Cu1 N2 C3 -137.30(12) . . . . ? N2 Cu1 N2 C13 167.60(12) 2_655 . . . ? N1 Cu1 N2 C13 80.05(12) . . . . ? N1 Cu1 N2 C13 -102.78(12) 2_655 . . . ? O1 Cu1 N2 C13 -12.40(12) . . . . ? C5 N1 C1 C2 -177.34(16) 2_655 . . . ? C6 N1 C1 C2 65.2(2) . . . . ? Cu1 N1 C1 C2 -64.72(17) . . . . ? N1 C1 C2 C3 71.7(2) . . . . ? C4 N2 C3 C2 173.26(16) . . . . ? C13 N2 C3 C2 -65.5(2) . . . . ? Cu1 N2 C3 C2 57.39(19) . . . . ? C1 C2 C3 N2 -65.7(2) . . . . ? C3 N2 C4 C5 -163.13(16) . . . . ? C13 N2 C4 C5 74.8(2) . . . . ? Cu1 N2 C4 C5 -41.96(18) . . . . ? N2 C4 C5 N1 57.0(2) . . . 2_655 ? C5 N1 C6 C7 -56.2(2) 2_655 . . . ? C1 N1 C6 C7 62.3(2) . . . . ? Cu1 N1 C6 C7 -172.35(13) . . . . ? N1 C6 C7 C8 90.0(2) . . . . ? N1 C6 C7 C12 -91.4(2) . . . . ? C12 C7 C8 C9 2.6(3) . . . . ? C6 C7 C8 C9 -178.9(2) . . . . ? C7 C8 C9 C10 -1.6(3) . . . . ? C8 C9 C10 C11 -0.3(4) . . . . ? C9 C10 C11 C12 1.2(3) . . . . ? C10 C11 C12 C7 -0.2(3) . . . . ? C8 C7 C12 C11 -1.6(3) . . . . ? C6 C7 C12 C11 179.83(19) . . . . ? C4 N2 C13 C14 53.8(2) . . . . ? C3 N2 C13 C14 -65.1(2) . . . . ? Cu1 N2 C13 C14 168.97(14) . . . . ? N2 C13 C14 C15 85.1(3) . . . . ? N2 C13 C14 C19 -100.3(2) . . . . ? C19 C14 C15 C16 0.3(4) . . . . ? C13 C14 C15 C16 175.0(2) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C16 C17 C18 C19 -0.8(5) . . . . ? C17 C18 C19 C14 0.9(5) . . . . ? C15 C14 C19 C18 -0.7(4) . . . . ? C13 C14 C19 C18 -175.5(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 O1 H1O O2 0.820(16) 2.038(18) 2.817(2) 158(3) . O5 H5O O4 0.84 1.94 2.779(4) 172.4 . _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.872 _refine_diff_density_min -0.646 _refine_diff_density_rms 0.099