Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 data_global # *** Added by check_cif _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' _publ_contact_author ; Pr Paul-Louis Fabre Laboratoire de Chimie Inorganique Universit\'e Paul Sabatier 118 Route de Narbonne 31062 Toulouse Cedex 04 France ; _publ_contact_author_phone '(33) 0561556100' _publ_contact_author_fax '(33) 0561556118' _publ_contact_author_email fabre@ramses.ups-tlse.fr _publ_requested_coeditor_name ? _publ_referenced_number ' B009239H ' _publ_section_title ; Complexation of 3,4-bis(cyanamido)cyclobutane-1,2-dione dianion with copper. Crystal structures and spectroscopic data of copper(I) and (II) complexes. ; loop_ _publ_author_name _publ_author_address 'Fabre, Paul-Louis' ; Laboratoire de Chimie Inorganique Universit\'e Paul Sabatier 118 Route de Narbonne 31062 Toulouse Cedex 04 France ; 'Galibert, Anne-Marie' ; Laboratoire de Chimie Inorganique Universit\'e Paul Sabatier 118 Route de Narbonne 31062 Toulouse Cedex 04 France ; 'Soula, Brigitte' ; Laboratoire de Chimie Inorganique Universit\'e Paul Sabatier 118 Route de Narbonne 31062 Toulouse Cedex 04 France ; 'Castan, Paule' ; Laboratoire de Chimie Inorganique Universit\'e Paul Sabatier 118 Route de Narbonne 31062 Toulouse Cedex 04 France ; 'Dahan, Fran\,coise' ; Laboratoire de Chimie de Coordination du CNRS 205 Route de Narbonne 31077 Toulouse Cedex 4 France ; data_(1) _database_code_CSD 153403 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C84 H69 Cu2 N7 O2 P4' _chemical_formula_weight 1459.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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 C2/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' '-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 12.744(3) _cell_length_b 22.012(4) _cell_length_c 25.191(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.40(3) _cell_angle_gamma 90.00 _cell_volume 7064(3) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Parallelepiped' _exptl_crystal_colour 'Yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3024 _exptl_absorpt_coefficient_mu 0.748 _exptl_absorpt_correction_type 'None' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'STOE-IPDS' _diffrn_measurement_method 'Imaging Plate Detector System' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12889 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 24.27 _reflns_number_total 5443 _reflns_number_gt 4616 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE-IPDS software (Stoe, 2.87, 1997)' _computing_cell_refinement 'STOE-IPDS software (Stoe, 2.87, 1997)' _computing_data_reduction 'XRED (Stoe, 1.08, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1996)' _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 w==1/[\s^2^(Fo^2^)+(0.0775P)^2^+2.4380P] 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 5443 _refine_ls_number_parameters 461 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.40986(2) 0.216501(12) 0.376984(12) 0.02708(13) Uani 1 d . . . P1 P 0.47939(5) 0.31024(3) 0.39684(3) 0.02962(17) Uani 1 d . . . P2 P 0.43876(5) 0.13128(3) 0.42823(3) 0.02984(17) Uani 1 d . . . O1 O 0.10848(17) 0.09588(9) 0.28721(9) 0.0485(5) Uani 1 d . . . N1 N 0.2681(2) 0.22001(10) 0.34005(10) 0.0393(5) Uani 1 d . . . N2 N 0.10563(19) 0.24339(10) 0.28916(10) 0.0397(5) Uani 1 d . . . N3 N 0.5114(2) 0.18356(11) 0.31608(10) 0.0425(6) Uani 1 d . . . C1 C 0.1902(2) 0.22712(11) 0.31611(11) 0.0348(6) Uani 1 d . . . C2 C 0.0461(2) 0.19953(12) 0.26666(11) 0.0337(6) Uani 1 d . . . C3 C 0.0489(2) 0.13327(12) 0.26699(12) 0.0381(6) Uani 1 d . . . C4 C 0.5847(3) 0.15993(13) 0.30122(11) 0.0407(7) Uani 1 d . . . C5 C 0.6784(3) 0.13087(18) 0.28341(15) 0.0656(10) Uani 1 d . . . H5A H 0.6995 0.1492 0.2498 0.072 Uiso 1 calc R . . H5B H 0.6650 0.0874 0.2781 0.072 Uiso 1 calc R . . H5C H 0.7348 0.1362 0.3102 0.072 Uiso 1 calc R . . C6 C 0.4405(2) 0.37295(11) 0.35362(11) 0.0329(6) Uani 1 d . . . C7 C 0.3577(2) 0.36561(12) 0.31752(12) 0.0402(7) Uani 1 d . . . H7 H 0.3216 0.3279 0.3153 0.044 Uiso 1 calc R . . C8 C 0.3273(3) 0.41328(14) 0.28458(14) 0.0525(8) Uani 1 d . . . H8 H 0.2705 0.4081 0.2599 0.058 Uiso 1 calc R . . C9 C 0.3791(3) 0.46818(14) 0.28739(14) 0.0519(8) Uani 1 d . . . H9 H 0.3576 0.5007 0.2649 0.057 Uiso 1 calc R . . C10 C 0.4616(3) 0.47583(13) 0.32254(14) 0.0490(8) Uani 1 d . . . H10 H 0.4977 0.5136 0.3242 0.054 Uiso 1 calc R . . C11 C 0.4924(2) 0.42862(12) 0.35556(13) 0.0427(7) Uani 1 d . . . H11 H 0.5497 0.4342 0.3799 0.047 Uiso 1 calc R . . C12 C 0.4635(2) 0.33873(11) 0.46445(11) 0.0329(6) Uani 1 d . . . C13 C 0.4375(3) 0.39851(13) 0.47699(13) 0.0450(7) Uani 1 d . . . H13 H 0.4311 0.4280 0.4495 0.049 Uiso 1 calc R . . C14 C 0.4208(3) 0.41535(15) 0.52932(14) 0.0514(8) Uani 1 d . . . H14 H 0.4035 0.4563 0.5373 0.057 Uiso 1 calc R . . C15 C 0.4292(3) 0.37342(15) 0.56942(13) 0.0498(8) Uani 1 d . . . H15 H 0.4175 0.3853 0.6051 0.055 Uiso 1 calc R . . C16 C 0.4544(3) 0.31442(14) 0.55811(12) 0.0463(7) Uani 1 d . . . H16 H 0.4602 0.2853 0.5859 0.051 Uiso 1 calc R . . C17 C 0.4714(2) 0.29723(13) 0.50583(12) 0.0387(6) Uani 1 d . . . H17 H 0.4888 0.2562 0.4983 0.043 Uiso 1 calc R . . C18 C 0.6210(2) 0.30825(11) 0.38759(11) 0.0318(6) Uani 1 d . . . C19 C 0.6948(2) 0.30674(11) 0.42860(12) 0.0358(6) Uani 1 d . . . H19 H 0.6732 0.3118 0.4642 0.039 Uiso 1 calc R . . C20 C 0.8004(2) 0.29783(13) 0.41840(14) 0.0447(7) Uani 1 d . . . H20 H 0.8506 0.2971 0.4469 0.049 Uiso 1 calc R . . C21 C 0.8325(2) 0.29003(12) 0.36714(14) 0.0466(8) Uani 1 d . . . H21 H 0.9045 0.2829 0.3604 0.051 Uiso 1 calc R . . C22 C 0.7608(2) 0.29258(12) 0.32571(13) 0.0432(7) Uani 1 d . . . H22 H 0.7833 0.2882 0.2902 0.048 Uiso 1 calc R . . C23 C 0.6550(2) 0.30159(12) 0.33576(12) 0.0374(6) Uani 1 d . . . H23 H 0.6055 0.3032 0.3070 0.041 Uiso 1 calc R . . C24 C 0.5743(2) 0.10390(11) 0.42491(10) 0.0314(6) Uani 1 d . . . C25 C 0.6550(2) 0.14554(12) 0.43224(11) 0.0379(6) Uani 1 d . . . H25 H 0.6386 0.1869 0.4391 0.042 Uiso 1 calc R . . C26 C 0.7585(2) 0.12795(13) 0.42973(12) 0.0432(7) Uani 1 d . . . H26 H 0.8128 0.1569 0.4354 0.048 Uiso 1 calc R . . C27 C 0.7834(3) 0.06808(14) 0.41890(13) 0.0468(7) Uani 1 d . . . H27 H 0.8547 0.0558 0.4169 0.051 Uiso 1 calc R . . C28 C 0.7041(3) 0.02671(14) 0.41116(14) 0.0502(8) Uani 1 d . . . H28 H 0.7206 -0.0145 0.4037 0.055 Uiso 1 calc R . . C29 C 0.6000(2) 0.04438(12) 0.41408(13) 0.0414(7) Uani 1 d . . . H29 H 0.5459 0.0152 0.4086 0.046 Uiso 1 calc R . . C30 C 0.3633(2) 0.06428(11) 0.40867(11) 0.0332(6) Uani 1 d . . . C31 C 0.3294(2) 0.02143(12) 0.44427(12) 0.0387(6) Uani 1 d . . . H31 H 0.3397 0.0281 0.4813 0.043 Uiso 1 calc R . . C32 C 0.2806(3) -0.03103(12) 0.42666(14) 0.0452(7) Uani 1 d . . . H32 H 0.2578 -0.0603 0.4516 0.050 Uiso 1 calc R . . C33 C 0.2650(2) -0.04101(12) 0.37325(14) 0.0460(7) Uani 1 d . . . H33 H 0.2324 -0.0775 0.3612 0.051 Uiso 1 calc R . . C34 C 0.2963(3) 0.00156(14) 0.33751(15) 0.0584(9) Uani 1 d . . . H34 H 0.2848 -0.0051 0.3006 0.064 Uiso 1 calc R . . C35 C 0.3453(3) 0.05489(14) 0.35522(13) 0.0562(9) Uani 1 d . . . H35 H 0.3662 0.0847 0.3303 0.062 Uiso 1 calc R . . C36 C 0.4162(2) 0.13603(11) 0.49902(10) 0.0307(6) Uani 1 d . . . C37 C 0.3280(2) 0.16756(12) 0.51516(11) 0.0373(6) Uani 1 d . . . H37 H 0.2818 0.1855 0.4895 0.041 Uiso 1 calc R . . C38 C 0.3076(2) 0.17276(14) 0.56890(13) 0.0443(7) Uani 1 d . . . H38 H 0.2471 0.1940 0.5799 0.049 Uiso 1 calc R . . C39 C 0.3748(2) 0.14717(13) 0.60623(12) 0.0420(7) Uani 1 d . . . H39 H 0.3612 0.1515 0.6430 0.046 Uiso 1 calc R . . C40 C 0.4613(2) 0.11542(12) 0.59047(11) 0.0394(6) Uani 1 d . . . H40 H 0.5067 0.0971 0.6163 0.043 Uiso 1 calc R . . C41 C 0.4828(2) 0.10997(11) 0.53696(11) 0.0350(6) Uani 1 d . . . H41 H 0.5433 0.0883 0.5263 0.038 Uiso 1 calc R . . N01 N 0.5000 0.1149(3) 0.7500 0.115(2) Uani 1 d S . . C01 C 0.5000 0.0623(3) 0.7500 0.133(4) Uani 1 d S . . C02 C 0.4705(14) 0.0026(4) 0.7320(5) 0.115(7) Uani 0.50 d P . . 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 Cu 0.02719(19) 0.02644(19) 0.0275(2) 0.00095(11) -0.00084(13) -0.00297(11) P1 0.0271(4) 0.0313(3) 0.0305(4) 0.0019(2) 0.0016(3) -0.0013(2) P2 0.0313(4) 0.0295(3) 0.0288(4) -0.0006(2) 0.0020(3) -0.0039(2) O1 0.0449(13) 0.0356(10) 0.0645(14) 0.0010(9) -0.0121(11) 0.0005(9) N1 0.0377(15) 0.0416(12) 0.0384(14) -0.0055(10) -0.0005(12) -0.0056(10) N2 0.0395(14) 0.0333(11) 0.0459(14) 0.0014(10) -0.0049(12) 0.0016(10) N3 0.0492(17) 0.0462(13) 0.0321(13) -0.0011(10) 0.0001(12) -0.0053(12) C1 0.0404(17) 0.0300(12) 0.0341(15) -0.0033(10) 0.0050(14) -0.0062(11) C2 0.0292(13) 0.0414(14) 0.0307(13) -0.0021(11) 0.0027(11) -0.0007(11) C3 0.0365(15) 0.0414(15) 0.0363(15) -0.0003(12) -0.0008(12) -0.0012(12) C4 0.0501(19) 0.0436(15) 0.0285(14) -0.0010(11) 0.0032(14) -0.0025(13) C5 0.069(3) 0.077(2) 0.052(2) -0.0025(17) 0.0162(19) 0.0170(19) C6 0.0283(14) 0.0367(13) 0.0339(14) 0.0039(10) 0.0068(12) 0.0005(10) C7 0.0427(17) 0.0390(14) 0.0388(16) 0.0058(11) -0.0008(14) -0.0025(12) C8 0.055(2) 0.0548(17) 0.0470(18) 0.0130(14) -0.0102(16) 0.0055(15) C9 0.061(2) 0.0432(16) 0.0513(19) 0.0164(13) 0.0041(17) 0.0050(14) C10 0.052(2) 0.0345(14) 0.061(2) 0.0081(13) 0.0132(17) -0.0028(12) C11 0.0385(16) 0.0384(14) 0.0513(18) 0.0051(12) 0.0021(14) -0.0044(12) C12 0.0268(13) 0.0382(13) 0.0338(14) -0.0019(11) 0.0007(11) -0.0036(10) C13 0.0471(18) 0.0407(14) 0.0471(18) -0.0030(13) 0.0005(15) 0.0058(12) C14 0.0469(18) 0.0528(17) 0.055(2) -0.0194(15) 0.0037(16) 0.0074(14) C15 0.0419(18) 0.071(2) 0.0371(17) -0.0132(15) 0.0059(14) -0.0058(15) C16 0.0458(18) 0.0579(18) 0.0354(16) 0.0006(13) 0.0015(14) -0.0089(14) C17 0.0403(16) 0.0391(13) 0.0366(15) -0.0021(11) 0.0025(13) -0.0039(11) C18 0.0294(14) 0.0267(12) 0.0392(15) 0.0024(10) 0.0024(12) -0.0051(10) C19 0.0336(15) 0.0354(13) 0.0382(15) 0.0040(11) -0.0009(13) -0.0048(11) C20 0.0309(15) 0.0433(14) 0.060(2) 0.0027(13) -0.0071(14) -0.0025(12) C21 0.0293(15) 0.0405(15) 0.070(2) -0.0032(13) 0.0111(16) -0.0007(11) C22 0.0376(17) 0.0421(15) 0.0506(19) -0.0052(12) 0.0147(15) -0.0044(12) C23 0.0351(15) 0.0344(13) 0.0428(16) -0.0034(11) 0.0024(13) -0.0041(11) C24 0.0361(15) 0.0347(13) 0.0237(13) 0.0021(10) 0.0037(11) -0.0024(10) C25 0.0383(16) 0.0381(13) 0.0373(15) -0.0009(11) 0.0003(13) -0.0042(11) C26 0.0349(16) 0.0502(16) 0.0447(17) -0.0017(13) 0.0031(14) -0.0082(12) C27 0.0356(16) 0.0559(17) 0.0490(18) -0.0017(14) 0.0064(14) 0.0050(13) C28 0.0457(19) 0.0431(16) 0.062(2) -0.0049(14) 0.0093(16) 0.0036(13) C29 0.0363(16) 0.0372(14) 0.0509(18) -0.0050(12) 0.0048(14) -0.0029(11) C30 0.0312(14) 0.0293(12) 0.0390(15) -0.0012(10) -0.0019(12) -0.0025(10) C31 0.0384(16) 0.0372(14) 0.0406(16) -0.0016(11) 0.0056(13) -0.0026(11) C32 0.0441(17) 0.0326(13) 0.059(2) 0.0019(12) 0.0082(15) -0.0069(12) C33 0.0338(15) 0.0337(14) 0.070(2) -0.0067(13) -0.0066(15) -0.0040(11) C34 0.076(3) 0.0510(18) 0.0471(19) -0.0072(14) -0.0190(18) -0.0157(16) C35 0.081(3) 0.0426(16) 0.0441(18) 0.0050(13) -0.0145(18) -0.0206(16) C36 0.0304(14) 0.0292(12) 0.0325(14) -0.0015(10) 0.0008(11) -0.0062(10) C37 0.0302(14) 0.0450(14) 0.0365(15) -0.0016(11) 0.0007(12) -0.0015(11) C38 0.0335(16) 0.0545(17) 0.0452(18) -0.0127(13) 0.0064(14) -0.0023(12) C39 0.0425(17) 0.0540(16) 0.0297(15) -0.0073(12) 0.0059(13) -0.0106(13) C40 0.0432(17) 0.0433(14) 0.0315(14) -0.0010(11) -0.0002(13) -0.0022(12) C41 0.0345(15) 0.0339(13) 0.0367(15) -0.0020(11) 0.0021(12) -0.0003(11) N01 0.139(7) 0.088(4) 0.114(5) 0.000 -0.041(5) 0.000 C01 0.121(7) 0.097(6) 0.185(10) 0.000 0.105(7) 0.000 C02 0.154(18) 0.074(5) 0.119(13) -0.017(6) 0.080(12) -0.030(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 Cu N1 2.013(3) . ? Cu N3 2.157(3) . ? Cu P1 2.2959(8) . ? Cu P2 2.3018(8) . ? P1 C6 1.819(3) . ? P1 C18 1.826(3) . ? P1 C12 1.831(3) . ? P2 C36 1.816(3) . ? P2 C30 1.822(3) . ? P2 C24 1.833(3) . ? O1 C3 1.223(4) . ? N1 C1 1.160(4) . ? N2 C1 1.309(4) . ? N2 C2 1.345(4) . ? N3 C4 1.140(4) . ? C2 C2 1.427(6) 2 ? C2 C3 1.459(4) . ? C3 C3 1.494(6) 2 ? C4 C5 1.437(5) . ? C6 C7 1.386(4) . ? C6 C11 1.392(4) . ? C7 C8 1.387(4) . ? C8 C9 1.378(5) . ? C9 C10 1.368(5) . ? C10 C11 1.382(4) . ? C12 C17 1.388(4) . ? C12 C13 1.395(4) . ? C13 C14 1.390(5) . ? C14 C15 1.371(5) . ? C15 C16 1.369(5) . ? C16 C17 1.392(4) . ? C18 C19 1.380(4) . ? C18 C23 1.393(4) . ? C19 C20 1.390(4) . ? C20 C21 1.375(5) . ? C21 C22 1.372(5) . ? C22 C23 1.392(4) . ? C24 C29 1.379(4) . ? C24 C25 1.386(4) . ? C25 C26 1.378(4) . ? C26 C27 1.384(4) . ? C27 C28 1.371(5) . ? C28 C29 1.386(4) . ? C30 C35 1.376(4) . ? C30 C31 1.378(4) . ? C31 C32 1.379(4) . ? C32 C33 1.373(5) . ? C33 C34 1.366(5) . ? C34 C35 1.398(4) . ? C36 C41 1.387(4) . ? C36 C37 1.390(4) . ? C37 C38 1.390(4) . ? C38 C39 1.377(5) . ? C39 C40 1.373(4) . ? C40 C41 1.387(4) . ? N01 C01 1.157(9) . ? C01 C02 1.436(11) 2_656 ? C01 C02 1.436(11) . ? C02 C02 1.16(3) 2_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu N3 103.37(10) . . ? N1 Cu P1 113.79(6) . . ? N3 Cu P1 102.83(7) . . ? N1 Cu P2 114.84(7) . . ? N3 Cu P2 91.97(7) . . ? P1 Cu P2 123.69(3) . . ? C6 P1 C18 101.38(12) . . ? C6 P1 C12 105.20(12) . . ? C18 P1 C12 105.01(13) . . ? C6 P1 Cu 116.97(9) . . ? C18 P1 Cu 109.15(8) . . ? C12 P1 Cu 117.37(9) . . ? C36 P2 C30 102.54(12) . . ? C36 P2 C24 103.62(12) . . ? C30 P2 C24 102.30(12) . . ? C36 P2 Cu 118.47(8) . . ? C30 P2 Cu 115.59(9) . . ? C24 P2 Cu 112.36(8) . . ? C1 N1 Cu 173.1(2) . . ? C1 N2 C2 118.1(2) . . ? C4 N3 Cu 153.8(2) . . ? N1 C1 N2 171.8(3) . . ? N2 C2 C2 134.11(16) . 2 ? N2 C2 C3 134.6(3) . . ? C2 C2 C3 91.32(15) 2 . ? O1 C3 C2 133.6(3) . . ? O1 C3 C3 137.68(16) . 2 ? C2 C3 C3 88.67(15) . 2 ? N3 C4 C5 178.7(3) . . ? C7 C6 C11 118.6(2) . . ? C7 C6 P1 119.7(2) . . ? C11 C6 P1 121.6(2) . . ? C6 C7 C8 120.1(3) . . ? C9 C8 C7 120.4(3) . . ? C10 C9 C8 120.1(3) . . ? C9 C10 C11 119.9(3) . . ? C10 C11 C6 120.9(3) . . ? C17 C12 C13 117.6(3) . . ? C17 C12 P1 117.7(2) . . ? C13 C12 P1 124.5(2) . . ? C14 C13 C12 120.6(3) . . ? C15 C14 C13 120.6(3) . . ? C16 C15 C14 120.0(3) . . ? C15 C16 C17 119.8(3) . . ? C12 C17 C16 121.4(3) . . ? C19 C18 C23 118.5(3) . . ? C19 C18 P1 124.2(2) . . ? C23 C18 P1 116.9(2) . . ? C18 C19 C20 120.7(3) . . ? C21 C20 C19 120.2(3) . . ? C22 C21 C20 120.1(3) . . ? C21 C22 C23 119.9(3) . . ? C22 C23 C18 120.7(3) . . ? C29 C24 C25 118.4(3) . . ? C29 C24 P2 123.4(2) . . ? C25 C24 P2 118.2(2) . . ? C26 C25 C24 121.1(3) . . ? C25 C26 C27 120.1(3) . . ? C28 C27 C26 119.3(3) . . ? C27 C28 C29 120.6(3) . . ? C24 C29 C28 120.6(3) . . ? C35 C30 C31 119.1(2) . . ? C35 C30 P2 117.4(2) . . ? C31 C30 P2 123.4(2) . . ? C30 C31 C32 120.6(3) . . ? C33 C32 C31 120.2(3) . . ? C34 C33 C32 119.9(3) . . ? C33 C34 C35 120.1(3) . . ? C30 C35 C34 120.1(3) . . ? C41 C36 C37 119.4(3) . . ? C41 C36 P2 123.0(2) . . ? C37 C36 P2 117.7(2) . . ? C38 C37 C36 119.9(3) . . ? C39 C38 C37 120.2(3) . . ? C40 C39 C38 120.1(3) . . ? C39 C40 C41 120.3(3) . . ? C36 C41 C40 120.1(3) . . ? C02 C01 C02 47.8(11) 2_656 . ? C02 C01 N01 156.1(5) 2_656 . ? C02 C01 N01 156.1(5) . . ? C02 C02 C01 66.1(5) 2_656 . ? _diffrn_measured_fraction_theta_max 0.462 _diffrn_reflns_theta_full 24.27 _diffrn_measured_fraction_theta_full 0.462 _refine_diff_density_max 0.476 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.061 #======END data_(2) _database_code_CSD 153404 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H36 Cu2 N14 O9' _chemical_formula_weight 743.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.9816(13) _cell_length_b 14.712(3) _cell_length_c 14.746(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.35(2) _cell_angle_gamma 90.00 _cell_volume 1514.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Plate' _exptl_crystal_colour 'Yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.631 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 1.476 _exptl_absorpt_correction_type 'None' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'STOE-IPDS' _diffrn_measurement_method 'Imaging Plate Detector System' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11671 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.88 _reflns_number_total 5417 _reflns_number_gt 5152 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE-IPDS software (Stoe, 2.87, 1997)' _computing_cell_refinement 'STOE-IPDS software (Stoe, 2.87, 1997)' _computing_data_reduction 'XRED (Stoe, 1.08, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1996)' _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 w==1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.005(9) _refine_ls_number_reflns 5417 _refine_ls_number_parameters 436 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0552 _refine_ls_wR_factor_gt 0.0551 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.006 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.38713(4) 0.256580(16) 0.490610(16) 0.01858(8) Uani 1 d . . . N1 N 0.4917(4) 0.36556(14) 0.55855(14) 0.0244(5) Uani 1 d . . . H1A H 0.5077 0.3513 0.6189 0.027 Uiso 1 calc R . . H1B H 0.6091 0.3815 0.5355 0.027 Uiso 1 calc R . . N2 N 0.1602(4) 0.33738(15) 0.46420(15) 0.0238(5) Uani 1 d . . . H2 H 0.1771 0.3660 0.4086 0.026 Uiso 1 calc R . . N3 N 0.2109(4) 0.15520(15) 0.44788(16) 0.0273(5) Uani 1 d . . . H3A H 0.2739 0.1186 0.4072 0.030 Uiso 1 calc R . . H3B H 0.1743 0.1201 0.4964 0.030 Uiso 1 calc R . . C1 C 0.3575(5) 0.44195(17) 0.54921(18) 0.0315(7) Uani 1 d . . . H1C H 0.3930 0.4794 0.4962 0.035 Uiso 1 calc R . . H1D H 0.3642 0.4808 0.6040 0.035 Uiso 1 calc R . . C2 C 0.1577(4) 0.40634(19) 0.53710(17) 0.0285(6) Uani 1 d . . . H2A H 0.1125 0.3787 0.5943 0.031 Uiso 1 calc R . . H2B H 0.0698 0.4566 0.5206 0.031 Uiso 1 calc R . . C3 C -0.0109(5) 0.2785(2) 0.4598(2) 0.0385(7) Uani 1 d . . . H3C H -0.1187 0.3112 0.4306 0.042 Uiso 1 calc R . . H3D H -0.0502 0.2603 0.5216 0.042 Uiso 1 calc R . . C4 C 0.0425(4) 0.19554(18) 0.40470(18) 0.0281(6) Uani 1 d . . . H4A H -0.0647 0.1515 0.4037 0.031 Uiso 1 calc R . . H4B H 0.0717 0.2132 0.3415 0.031 Uiso 1 calc R . . N4 N 0.5209(4) 0.27308(14) 0.35224(13) 0.0253(5) Uani 1 d . . . C5 C 0.5705(4) 0.33172(15) 0.30400(15) 0.0160(5) Uani 1 d . . . N6 N 0.6233(3) 0.39157(14) 0.24196(12) 0.0182(4) Uani 1 d . . . C6 C 0.6922(3) 0.46920(15) 0.27279(15) 0.0150(4) Uani 1 d . . . C7 C 0.7446(4) 0.51270(16) 0.35916(15) 0.0186(5) Uani 1 d . . . C8 C 0.7977(3) 0.59678(15) 0.30684(14) 0.0159(4) Uani 1 d . . . C9 C 0.7565(4) 0.54715(15) 0.22391(15) 0.0180(5) Uani 1 d . . . O1 O 0.7452(3) 0.48868(11) 0.43932(11) 0.0223(4) Uani 1 d . . . O2 O 0.8536(3) 0.67360(11) 0.32870(11) 0.0238(4) Uani 1 d . . . N7 N 0.7628(3) 0.55910(13) 0.13359(12) 0.0193(4) Uani 1 d . . . C10 C 0.8504(4) 0.62725(14) 0.09842(14) 0.0157(4) Uani 1 d . . . N8 N 0.9275(4) 0.68096(14) 0.05453(15) 0.0245(5) Uani 1 d . . . N5 N 0.5815(4) 0.17789(14) 0.54586(15) 0.0241(5) Uani 1 d . . . C11 C 0.6583(4) 0.12553(15) 0.59431(14) 0.0178(5) Uani 1 d . . . N9 N 0.7427(3) 0.05860(14) 0.63309(12) 0.0218(4) Uani 1 d . . . C12 C 0.7452(4) 0.04820(15) 0.72337(15) 0.0156(4) Uani 1 d . . . C13 C 0.6958(4) 0.09819(15) 0.80596(14) 0.0170(5) Uani 1 d . . . C14 C 0.7486(4) 0.01506(15) 0.85937(15) 0.0178(5) Uani 1 d . . . C15 C 0.8039(4) -0.02857(16) 0.77355(15) 0.0186(5) Uani 1 d . . . O3 O 0.6413(3) 0.17595(11) 0.82329(11) 0.0217(4) Uani 1 d . . . O4 O 0.7457(3) -0.00728(11) 0.93858(11) 0.0230(4) Uani 1 d . . . N10 N 0.8772(3) -0.10734(14) 0.74795(12) 0.0178(4) Uani 1 d . . . C16 C 0.9225(4) -0.16580(15) 0.81161(15) 0.0176(5) Uani 1 d . . . N11 N 0.9712(4) -0.22235(14) 0.86101(14) 0.0269(5) Uani 1 d . . . Cu2 Cu 1.11514(4) 0.761449(16) -0.003833(16) 0.01852(8) Uani 1 d . . . N12 N 1.0101(4) 0.86988(14) 0.06422(14) 0.0242(5) Uani 1 d . . . H12A H 0.8908 0.8844 0.0418 0.027 Uiso 1 calc R . . H12B H 0.9976 0.8554 0.1246 0.027 Uiso 1 calc R . . N13 N 1.3420(3) 0.84364(14) -0.02553(13) 0.0190(4) Uani 1 d . . . H13 H 1.3280 0.8721 -0.0815 0.021 Uiso 1 calc R . . N14 N 1.2882(4) 0.66157(16) -0.04929(15) 0.0281(5) Uani 1 d . . . H14A H 1.3151 0.6216 -0.0029 0.031 Uiso 1 calc R . . H14B H 1.2277 0.6300 -0.0951 0.031 Uiso 1 calc R . . C17 C 1.1393(4) 0.94916(16) 0.05480(18) 0.0258(6) Uani 1 d . . . H17A H 1.1283 0.9893 0.1084 0.028 Uiso 1 calc R . . H17B H 1.1046 0.9846 0.0001 0.028 Uiso 1 calc R . . C18 C 1.3458(4) 0.91294(18) 0.04684(18) 0.0278(6) Uani 1 d . . . H18A H 1.4347 0.9628 0.0310 0.031 Uiso 1 calc R . . H18B H 1.3883 0.8857 0.1049 0.031 Uiso 1 calc R . . C19 C 1.5154(5) 0.78514(18) -0.0266(2) 0.0332(7) Uani 1 d . . . H19A H 1.5512 0.7671 0.0359 0.037 Uiso 1 calc R . . H19B H 1.6244 0.8183 -0.0536 0.037 Uiso 1 calc R . . C20 C 1.4667(5) 0.70136(19) -0.08323(18) 0.0337(7) Uani 1 d . . . H20A H 1.4510 0.7187 -0.1477 0.037 Uiso 1 calc R . . H20B H 1.5718 0.6564 -0.0787 0.037 Uiso 1 calc R . . O1W O 0.6234(3) 0.80738(15) 0.24149(15) 0.0390(6) Uani 1 d . . . H1W1 H 0.551(4) 0.7480(19) 0.224(2) 0.043 Uiso 1 d . . . H2W1 H 0.750(4) 0.782(2) 0.269(2) 0.043 Uiso 1 d . . . O2W O 0.8755(4) 0.30014(14) 0.73345(15) 0.0355(5) Uani 1 d . . . H1W2 H 0.977(4) 0.268(2) 0.7126(19) 0.039 Uiso 1 d . . . H2W2 H 0.809(4) 0.260(2) 0.7679(18) 0.039 Uiso 1 d . . . O3W O 0.4315(4) 0.08737(16) 0.27899(17) 0.0476(6) Uani 1 d . . . H1W3 H 0.376(6) 0.078(2) 0.3404(17) 0.052 Uiso 1 d . . . H2W3 H 0.479(6) 0.0251(19) 0.252(2) 0.052 Uiso 1 d . . . O4W O 0.8997(4) 0.48794(16) 0.71148(18) 0.0519(6) Uani 1 d . . . H1W4 H 0.749(4) 0.492(2) 0.709(3) 0.057 Uiso 1 d . . . H2W4 H 0.918(5) 0.4188(18) 0.727(3) 0.057 Uiso 1 d . . . O5W O 0.7290(5) 0.99343(19) 0.20568(19) 0.0535(7) Uani 1 d . . . H1W5 H 0.850(4) 0.997(3) 0.235(3) 0.059 Uiso 1 d . . . H2W5 H 0.664(6) 0.931(2) 0.203(3) 0.059 Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01795(17) 0.01743(15) 0.02035(13) 0.00510(13) -0.00088(10) -0.00020(13) N1 0.0288(15) 0.0228(10) 0.0215(10) 0.0042(8) 0.0026(9) -0.0002(9) N2 0.0206(14) 0.0247(10) 0.0260(11) 0.0028(8) 0.0053(9) 0.0039(9) N3 0.0284(15) 0.0210(10) 0.0324(12) 0.0147(9) -0.0026(10) -0.0062(9) C1 0.047(2) 0.0232(12) 0.0245(12) 0.0009(10) -0.0060(12) 0.0021(11) C2 0.0291(17) 0.0368(14) 0.0195(11) 0.0048(10) 0.0052(10) 0.0115(12) C3 0.0332(19) 0.0514(19) 0.0308(13) -0.0119(12) -0.0106(12) 0.0065(13) C4 0.0230(17) 0.0325(13) 0.0288(13) 0.0075(10) -0.0069(11) -0.0050(11) N4 0.0291(14) 0.0224(10) 0.0246(9) 0.0056(8) 0.0046(8) -0.0047(9) C5 0.0139(13) 0.0139(10) 0.0201(11) -0.0033(8) -0.0031(9) 0.0008(8) N6 0.0248(13) 0.0160(9) 0.0140(9) 0.0004(7) 0.0070(8) -0.0017(7) C6 0.0089(13) 0.0162(10) 0.0201(11) 0.0026(8) 0.0038(9) 0.0001(9) C7 0.0138(13) 0.0268(12) 0.0152(10) -0.0003(9) 0.0034(8) 0.0047(9) C8 0.0131(13) 0.0165(10) 0.0181(10) -0.0018(8) 0.0010(8) -0.0036(8) C9 0.0208(15) 0.0181(11) 0.0152(10) -0.0012(8) 0.0066(9) 0.0003(9) O1 0.0282(11) 0.0238(8) 0.0149(8) 0.0008(6) -0.0017(7) -0.0014(7) O2 0.0274(12) 0.0215(8) 0.0226(8) -0.0032(6) 0.0056(7) -0.0049(7) N7 0.0249(13) 0.0166(9) 0.0165(9) 0.0019(7) 0.0066(8) -0.0043(8) C10 0.0141(13) 0.0154(10) 0.0178(10) -0.0023(8) 0.0029(8) 0.0018(8) N8 0.0278(14) 0.0227(11) 0.0232(10) 0.0082(8) 0.0029(9) -0.0027(9) N5 0.0192(14) 0.0263(11) 0.0267(11) 0.0055(9) -0.0027(9) 0.0048(9) C11 0.0197(15) 0.0190(11) 0.0147(10) -0.0004(8) 0.0059(9) -0.0059(9) N9 0.0293(14) 0.0192(9) 0.0168(9) -0.0003(7) -0.0020(8) 0.0046(8) C12 0.0092(13) 0.0161(10) 0.0216(10) 0.0027(8) 0.0005(8) 0.0004(8) C13 0.0196(14) 0.0141(10) 0.0173(10) 0.0013(8) -0.0021(9) -0.0053(9) C14 0.0150(14) 0.0172(11) 0.0211(11) -0.0016(8) 0.0001(9) -0.0025(9) C15 0.0222(15) 0.0199(11) 0.0136(10) 0.0034(8) -0.0028(9) -0.0013(10) O3 0.0253(11) 0.0174(8) 0.0225(8) -0.0009(6) 0.0028(7) 0.0022(7) O4 0.0309(12) 0.0205(8) 0.0175(8) 0.0001(6) -0.0007(7) -0.0014(7) N10 0.0175(12) 0.0164(9) 0.0195(9) 0.0009(7) -0.0011(8) 0.0009(7) C16 0.0183(14) 0.0171(10) 0.0172(10) -0.0009(9) -0.0031(9) 0.0006(9) N11 0.0296(14) 0.0230(10) 0.0282(10) 0.0011(8) -0.0009(9) 0.0035(9) Cu2 0.01855(18) 0.01709(14) 0.01996(13) 0.00511(12) 0.00437(10) 0.00098(13) N12 0.0272(14) 0.0205(10) 0.0248(10) 0.0057(8) 0.0056(9) -0.0021(8) N13 0.0168(12) 0.0252(10) 0.0150(9) 0.0040(8) 0.0041(8) -0.0038(8) N14 0.0325(16) 0.0293(11) 0.0226(11) 0.0094(8) 0.0014(10) 0.0092(10) C17 0.0235(16) 0.0211(12) 0.0329(13) 0.0060(10) 0.0038(11) -0.0037(10) C18 0.0309(18) 0.0242(12) 0.0283(12) -0.0031(10) 0.0021(11) -0.0058(11) C19 0.0188(18) 0.0241(13) 0.0568(18) 0.0016(11) 0.0088(13) 0.0053(10) C20 0.040(2) 0.0319(14) 0.0295(14) 0.0064(11) 0.0002(12) 0.0035(12) O1W 0.0281(14) 0.0279(10) 0.0608(15) -0.0057(9) -0.0160(11) -0.0010(8) O2W 0.0381(15) 0.0229(9) 0.0459(11) 0.0058(9) 0.0234(10) 0.0019(8) O3W 0.0490(17) 0.0383(12) 0.0555(13) -0.0012(11) 0.0137(12) -0.0103(11) O4W 0.062(2) 0.0386(12) 0.0548(15) 0.0028(10) 0.0086(13) 0.0025(12) O5W 0.056(2) 0.0557(15) 0.0489(15) 0.0005(12) -0.0007(13) 0.0095(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 N5 1.957(2) . ? Cu1 N2 2.017(2) . ? Cu1 N1 2.024(2) . ? Cu1 N3 2.031(2) . ? Cu1 N4 2.262(2) . ? N1 C1 1.469(4) . ? N1 H1A 0.9200 . ? N1 H1B 0.9200 . ? N2 C3 1.477(4) . ? N2 C2 1.478(3) . ? N2 H2 0.9300 . ? N3 C4 1.460(4) . ? N3 H3A 0.9200 . ? N3 H3B 0.9200 . ? C1 C2 1.499(5) . ? C1 H1C 0.9900 . ? C1 H1D 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.514(4) . ? C3 H3C 0.9900 . ? C3 H3D 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N4 C5 1.172(3) . ? C5 N6 1.324(3) . ? N6 C6 1.319(3) . ? C6 C9 1.429(3) . ? C6 C7 1.470(3) . ? C7 O1 1.234(3) . ? C7 C8 1.505(3) . ? C8 O2 1.238(3) . ? C8 C9 1.452(3) . ? C9 N7 1.344(3) . ? N7 C10 1.285(3) . ? C10 N8 1.157(3) . ? N8 Cu2 1.968(2) . ? N5 C11 1.178(3) . ? C11 N9 1.281(3) . ? N9 C12 1.340(3) . ? C12 C15 1.410(3) . ? C12 C13 1.466(3) . ? C13 O3 1.233(3) . ? C13 C14 1.499(3) . ? C14 O4 1.214(3) . ? C14 C15 1.473(3) . ? C15 N10 1.323(3) . ? N10 C16 1.310(3) . ? C16 N11 1.156(3) . ? N11 Cu2 2.239(2) 1_546 ? Cu2 N13 2.020(2) . ? Cu2 N14 2.020(2) . ? Cu2 N12 2.024(2) . ? Cu2 N11 2.239(2) 1_564 ? N12 C17 1.482(3) . ? N12 H12A 0.9200 . ? N12 H12B 0.9200 . ? N13 C18 1.476(3) . ? N13 C19 1.486(4) . ? N13 H13 0.9300 . ? N14 C20 1.468(4) . ? N14 H14A 0.9200 . ? N14 H14B 0.9200 . ? C17 C18 1.542(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.526(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? O1W H1W1 1.04(3) . ? O1W H2W1 1.04(3) . ? O2W H1W2 0.91(3) . ? O2W H2W2 0.91(3) . ? O3W H1W3 1.00(3) . ? O3W H2W3 1.05(3) . ? O4W H1W4 1.06(3) . ? O4W H2W4 1.05(3) . ? O5W H1W5 0.94(3) . ? O5W H2W5 1.03(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 N5 Cu1 N2 166.10(9) . . ? N5 Cu1 N1 90.89(10) . . ? N2 Cu1 N1 84.79(10) . . ? N5 Cu1 N3 96.42(10) . . ? N2 Cu1 N3 84.22(10) . . ? N1 Cu1 N3 161.98(11) . . ? N5 Cu1 N4 98.62(9) . . ? N2 Cu1 N4 95.21(9) . . ? N1 Cu1 N4 102.22(9) . . ? N3 Cu1 N4 92.96(9) . . ? C1 N1 Cu1 109.37(17) . . ? C1 N1 H1A 109.8 . . ? Cu1 N1 H1A 109.8 . . ? C1 N1 H1B 109.8 . . ? Cu1 N1 H1B 109.8 . . ? H1A N1 H1B 108.2 . . ? C3 N2 C2 114.9(2) . . ? C3 N2 Cu1 107.27(17) . . ? C2 N2 Cu1 106.08(17) . . ? C3 N2 H2 109.5 . . ? C2 N2 H2 109.5 . . ? Cu1 N2 H2 109.5 . . ? C4 N3 Cu1 108.75(16) . . ? C4 N3 H3A 109.9 . . ? Cu1 N3 H3A 109.9 . . ? C4 N3 H3B 109.9 . . ? Cu1 N3 H3B 109.9 . . ? H3A N3 H3B 108.3 . . ? N1 C1 C2 109.6(2) . . ? N1 C1 H1C 109.7 . . ? C2 C1 H1C 109.7 . . ? N1 C1 H1D 109.7 . . ? C2 C1 H1D 109.7 . . ? H1C C1 H1D 108.2 . . ? N2 C2 C1 108.1(2) . . ? N2 C2 H2A 110.1 . . ? C1 C2 H2A 110.1 . . ? N2 C2 H2B 110.1 . . ? C1 C2 H2B 110.1 . . ? H2A C2 H2B 108.4 . . ? N2 C3 C4 107.1(3) . . ? N2 C3 H3C 110.3 . . ? C4 C3 H3C 110.3 . . ? N2 C3 H3D 110.3 . . ? C4 C3 H3D 110.3 . . ? H3C C3 H3D 108.5 . . ? N3 C4 C3 107.1(2) . . ? N3 C4 H4A 110.3 . . ? C3 C4 H4A 110.3 . . ? N3 C4 H4B 110.3 . . ? C3 C4 H4B 110.3 . . ? H4A C4 H4B 108.6 . . ? C5 N4 Cu1 138.73(18) . . ? N4 C5 N6 173.6(2) . . ? C6 N6 C5 116.11(18) . . ? N6 C6 C9 129.5(2) . . ? N6 C6 C7 139.8(2) . . ? C9 C6 C7 90.59(19) . . ? O1 C7 C6 134.8(2) . . ? O1 C7 C8 136.6(2) . . ? C6 C7 C8 88.54(16) . . ? O2 C8 C9 137.7(2) . . ? O2 C8 C7 134.0(2) . . ? C9 C8 C7 88.31(17) . . ? N7 C9 C6 128.1(2) . . ? N7 C9 C8 139.6(2) . . ? C6 C9 C8 92.28(18) . . ? C10 N7 C9 121.4(2) . . ? N8 C10 N7 169.4(2) . . ? C10 N8 Cu2 165.8(2) . . ? C11 N5 Cu1 162.0(2) . . ? N5 C11 N9 168.7(2) . . ? C11 N9 C12 122.3(2) . . ? N9 C12 C15 127.9(2) . . ? N9 C12 C13 140.0(2) . . ? C15 C12 C13 92.00(18) . . ? O3 C13 C12 135.4(2) . . ? O3 C13 C14 136.3(2) . . ? C12 C13 C14 88.21(17) . . ? O4 C14 C15 135.6(2) . . ? O4 C14 C13 136.1(2) . . ? C15 C14 C13 88.23(17) . . ? N10 C15 C12 131.6(2) . . ? N10 C15 C14 137.0(2) . . ? C12 C15 C14 91.43(19) . . ? C16 N10 C15 117.56(19) . . ? N11 C16 N10 173.1(3) . . ? C16 N11 Cu2 140.03(18) . 1_546 ? N8 Cu2 N13 162.61(9) . . ? N8 Cu2 N14 96.23(10) . . ? N13 Cu2 N14 84.93(10) . . ? N8 Cu2 N12 90.76(9) . . ? N13 Cu2 N12 83.88(9) . . ? N14 Cu2 N12 163.16(11) . . ? N8 Cu2 N11 99.03(9) . 1_564 ? N13 Cu2 N11 98.24(8) . 1_564 ? N14 Cu2 N11 92.76(9) . 1_564 ? N12 Cu2 N11 101.27(9) . 1_564 ? C17 N12 Cu2 110.57(17) . . ? C17 N12 H12A 109.5 . . ? Cu2 N12 H12A 109.5 . . ? C17 N12 H12B 109.5 . . ? Cu2 N12 H12B 109.5 . . ? H12A N12 H12B 108.1 . . ? C18 N13 C19 113.4(2) . . ? C18 N13 Cu2 108.04(16) . . ? C19 N13 Cu2 107.15(16) . . ? C18 N13 H13 109.4 . . ? C19 N13 H13 109.4 . . ? Cu2 N13 H13 109.4 . . ? C20 N14 Cu2 109.51(18) . . ? C20 N14 H14A 109.8 . . ? Cu2 N14 H14A 109.8 . . ? C20 N14 H14B 109.8 . . ? Cu2 N14 H14B 109.8 . . ? H14A N14 H14B 108.2 . . ? N12 C17 C18 107.8(2) . . ? N12 C17 H17A 110.2 . . ? C18 C17 H17A 110.2 . . ? N12 C17 H17B 110.2 . . ? C18 C17 H17B 110.2 . . ? H17A C17 H17B 108.5 . . ? N13 C18 C17 106.3(2) . . ? N13 C18 H18A 110.5 . . ? C17 C18 H18A 110.5 . . ? N13 C18 H18B 110.5 . . ? C17 C18 H18B 110.5 . . ? H18A C18 H18B 108.7 . . ? N13 C19 C20 107.1(2) . . ? N13 C19 H19A 110.3 . . ? C20 C19 H19A 110.3 . . ? N13 C19 H19B 110.3 . . ? C20 C19 H19B 110.3 . . ? H19A C19 H19B 108.5 . . ? N14 C20 C19 108.8(2) . . ? N14 C20 H20A 109.9 . . ? C19 C20 H20A 109.9 . . ? N14 C20 H20B 109.9 . . ? C19 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? H1W1 O1W H2W1 102(2) . . ? H1W2 O2W H2W2 104(3) . . ? H1W3 O3W H2W3 110(3) . . ? H1W4 O4W H2W4 100(3) . . ? H1W5 O5W H2W5 117(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 N1 H1A O1W 0.92 2.35 3.178(3) 149.8 2_646 N1 H1B O1 0.92 2.33 3.089(3) 140.1 . N2 H2 N10 0.93 2.37 3.241(3) 156.1 2_656 N3 H3A O3W 0.92 2.24 3.101(4) 155.4 . N3 H3B O1 0.92 2.22 2.976(3) 138.5 2_646 N12 H12A O4 0.92 2.42 3.173(3) 138.9 1_564 N12 H12B O2W 0.92 2.41 3.250(3) 151.9 2_756 N13 H13 N6 0.93 2.41 3.279(3) 155.6 2_755 N14 H14A O4 0.92 2.16 2.983(3) 147.8 2_756 N14 H14B O5W 0.92 2.61 3.384(4) 142.6 2_745 O1W H1W1 O3 1.04(3) 1.84(3) 2.837(3) 158(3) 2_656 O1W H2W1 O2 1.04(3) 1.95(3) 2.843(3) 141(3) . O1W H2W1 O2W 1.04(3) 2.63(3) 3.517(4) 143(3) 2_756 O2W H1W2 O2 0.91(3) 1.92(3) 2.811(3) 165(3) 2_746 O2W H2W2 O3 0.91(3) 1.89(3) 2.792(3) 170(3) . O3W H1W3 N3 1.00(3) 2.27(3) 3.101(4) 140(3) . O3W H2W3 O5W 1.05(3) 1.93(4) 2.724(4) 129(3) 1_545 O4W H1W4 O3W 1.06(3) 1.89(3) 2.741(4) 135(3) 2_656 O4W H2W4 O2W 1.05(3) 1.77(3) 2.787(3) 161(3) . O5W H1W5 O4W 0.94(3) 1.92(3) 2.860(4) 172(4) 2_756 O5W H2W5 O1W 1.03(3) 1.92(3) 2.884(4) 154(3) . _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 25.88 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 0.427 _refine_diff_density_min -0.525 _refine_diff_density_rms 0.061 #======END data_(3) _database_code_CSD 153405 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 Cu N8 O2' _chemical_formula_weight 369.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 15.085(3) _cell_length_b 12.966(2) _cell_length_c 7.6366(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1493.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Plate' _exptl_crystal_colour 'Light-yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 1.487 _exptl_absorpt_correction_type 'None' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'STOE-IPDS' _diffrn_measurement_method 'Imaging Plate Detector System' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11033 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.92 _reflns_number_total 2877 _reflns_number_gt 2599 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE-IPDS software (Stoe, 2.87, 1997)' _computing_cell_refinement 'STOE-IPDS software (Stoe, 2.87, 1997)' _computing_data_reduction 'XRED (Stoe, 1.08, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1996)' _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 w==1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.008(14) _refine_ls_number_reflns 2877 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0643 _refine_ls_wR_factor_gt 0.0622 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.002 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.646540(18) 0.32146(2) 0.40588(5) 0.01023(9) Uani 1 d . . . N1 N 0.54863(17) 0.2929(2) 0.2292(4) 0.0151(5) Uani 1 d . . . H1A H 0.5317 0.2248 0.2345 0.017 Uiso 1 calc R . . H1B H 0.5000 0.3334 0.2525 0.017 Uiso 1 calc R . . N2 N 0.70829(16) 0.18454(19) 0.4966(4) 0.0174(5) Uani 1 d . . . H2A H 0.7466 0.1991 0.5869 0.019 Uiso 1 calc R . . H2B H 0.6664 0.1384 0.5359 0.019 Uiso 1 calc R . . N3 N 0.71628(16) 0.45605(18) 0.4534(3) 0.0164(6) Uani 1 d . . . H3A H 0.6804 0.5122 0.4340 0.018 Uiso 1 calc R . . H3B H 0.7348 0.4576 0.5681 0.018 Uiso 1 calc R . . N4 N 0.73029(16) 0.30616(18) 0.1960(3) 0.0151(5) Uani 1 d . . . C1 C 0.5843(2) 0.3169(3) 0.0558(4) 0.0210(7) Uani 1 d . . . H1C H 0.5863 0.3925 0.0386 0.023 Uiso 1 calc R . . H1D H 0.5459 0.2868 -0.0361 0.023 Uiso 1 calc R . . C2 C 0.6774(2) 0.2719(3) 0.0432(4) 0.0219(7) Uani 1 d . . . H2C H 0.6742 0.1956 0.0410 0.024 Uiso 1 calc R . . H2D H 0.7061 0.2952 -0.0665 0.024 Uiso 1 calc R . . C3 C 0.7566(2) 0.1417(2) 0.3472(5) 0.0256(8) Uani 1 d . . . H3C H 0.7153 0.1023 0.2718 0.028 Uiso 1 calc R . . H3D H 0.8031 0.0940 0.3893 0.028 Uiso 1 calc R . . C4 C 0.7987(2) 0.2283(2) 0.2420(5) 0.0220(7) Uani 1 d . . . H4A H 0.8463 0.2611 0.3116 0.024 Uiso 1 calc R . . H4B H 0.8254 0.1999 0.1338 0.024 Uiso 1 calc R . . C5 C 0.79368(19) 0.4601(2) 0.3355(4) 0.0184(6) Uani 1 d . . . H5A H 0.8444 0.4236 0.3896 0.020 Uiso 1 calc R . . H5B H 0.8111 0.5327 0.3151 0.020 Uiso 1 calc R . . C6 C 0.7697(2) 0.4096(2) 0.1643(4) 0.0184(6) Uani 1 d . . . H6A H 0.7268 0.4533 0.1004 0.020 Uiso 1 calc R . . H6B H 0.8235 0.4024 0.0909 0.020 Uiso 1 calc R . . N5 N 0.55874(17) 0.34176(19) 0.6038(4) 0.0140(5) Uani 1 d . . . C7 C 0.49098(19) 0.2770(2) 0.6433(4) 0.0114(6) Uani 1 d . . . C8 C 0.40439(19) 0.2884(2) 0.7258(4) 0.0169(6) Uani 1 d . . . C9 C 0.39101(19) 0.1745(2) 0.7071(4) 0.0154(6) Uani 1 d . . . C10 C 0.47958(19) 0.1687(2) 0.6238(4) 0.0141(6) Uani 1 d . . . O1 O 0.35985(15) 0.36028(19) 0.7842(3) 0.0303(6) Uani 1 d . . . O2 O 0.33174(14) 0.11343(18) 0.7422(3) 0.0243(5) Uani 1 d . . . C11 C 0.55435(19) 0.4361(2) 0.6705(4) 0.0172(6) Uani 1 d . . . N6 N 0.55935(18) 0.5185(2) 0.7276(4) 0.0258(6) Uani 1 d . . . N7 N 0.53097(16) 0.09628(19) 0.5566(4) 0.0188(6) Uani 1 d . . . C12 C 0.5032(2) -0.0004(3) 0.5629(5) 0.0239(7) Uani 1 d . . . N8 N 0.4875(2) -0.0878(2) 0.5613(5) 0.0381(8) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.01034(14) 0.01043(13) 0.00992(14) -0.00004(19) 0.0008(2) -0.00056(12) N1 0.0151(12) 0.0157(12) 0.0145(13) -0.0006(11) -0.0007(11) -0.0027(11) N2 0.0124(11) 0.0163(12) 0.0234(14) 0.0077(11) 0.0025(11) 0.0020(10) N3 0.0195(12) 0.0130(11) 0.0167(15) 0.0004(9) 0.0007(9) -0.0040(9) N4 0.0153(12) 0.0161(12) 0.0139(13) 0.0000(10) 0.0009(10) -0.0009(10) C1 0.0229(16) 0.0285(17) 0.0117(15) 0.0024(12) -0.0060(12) -0.0067(14) C2 0.0268(16) 0.0263(17) 0.0124(14) -0.0051(12) 0.0053(13) -0.0054(13) C3 0.0241(16) 0.0158(14) 0.037(2) 0.0043(12) 0.0118(14) 0.0061(13) C4 0.0160(15) 0.0226(16) 0.0272(17) 0.0018(13) 0.0087(14) 0.0061(12) C5 0.0169(14) 0.0194(14) 0.0189(14) 0.0014(12) 0.0009(12) -0.0071(11) C6 0.0181(15) 0.0226(16) 0.0146(14) 0.0041(12) 0.0022(13) -0.0070(12) N5 0.0154(13) 0.0117(12) 0.0149(13) -0.0035(10) 0.0026(11) -0.0011(10) C7 0.0127(14) 0.0142(14) 0.0073(14) -0.0010(10) -0.0009(11) 0.0005(11) C8 0.0133(14) 0.0239(14) 0.0136(14) -0.0039(12) -0.0011(12) -0.0006(11) C9 0.0128(13) 0.0244(15) 0.0090(14) 0.0004(12) -0.0007(11) -0.0017(12) C10 0.0132(13) 0.0190(14) 0.0100(14) -0.0001(11) -0.0003(11) -0.0016(12) O1 0.0209(11) 0.0324(12) 0.0376(14) -0.0147(11) 0.0069(11) 0.0064(9) O2 0.0209(11) 0.0345(12) 0.0177(11) -0.0035(10) 0.0038(10) -0.0110(9) C11 0.0149(14) 0.0201(16) 0.0167(14) 0.0018(12) 0.0011(13) -0.0005(12) N6 0.0238(14) 0.0190(14) 0.0347(17) -0.0099(12) 0.0026(13) 0.0017(11) N7 0.0139(12) 0.0141(12) 0.0284(15) -0.0026(11) 0.0052(11) -0.0019(10) C12 0.0180(15) 0.0243(17) 0.029(2) 0.0002(14) 0.0043(14) 0.0000(12) N8 0.0378(18) 0.0186(16) 0.058(2) 0.0012(14) 0.0046(16) -0.0041(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 Cu N5 2.027(3) . ? Cu N1 2.035(3) . ? Cu N4 2.050(3) . ? Cu N3 2.070(2) . ? Cu N2 2.121(2) . ? N1 C1 1.463(4) . ? N1 H1A 0.9200 . ? N1 H1B 0.9200 . ? N2 C3 1.463(4) . ? N2 H2A 0.9200 . ? N2 H2B 0.9200 . ? N3 C5 1.475(4) . ? N3 H3A 0.9200 . ? N3 H3B 0.9200 . ? N4 C2 1.482(4) . ? N4 C4 1.486(4) . ? N4 C6 1.487(4) . ? C1 C2 1.524(5) . ? C1 H1C 0.9900 . ? C1 H1D 0.9900 . ? C2 H2C 0.9900 . ? C2 H2D 0.9900 . ? C3 C4 1.519(4) . ? C3 H3C 0.9900 . ? C3 H3D 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.506(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N5 C11 1.327(4) . ? N5 C7 1.357(4) . ? C7 C10 1.422(4) . ? C7 C8 1.458(4) . ? C8 O1 1.232(4) . ? C8 C9 1.498(4) . ? C9 O2 1.224(4) . ? C9 C10 1.481(4) . ? C10 N7 1.322(4) . ? C11 N6 1.156(4) . ? N7 C12 1.323(4) . ? C12 N8 1.158(5) . ? 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 N5 Cu N1 92.52(10) . . ? N5 Cu N4 176.48(11) . . ? N1 Cu N4 84.91(11) . . ? N5 Cu N3 95.27(10) . . ? N1 Cu N3 129.70(10) . . ? N4 Cu N3 84.57(9) . . ? N5 Cu N2 98.75(10) . . ? N1 Cu N2 112.51(11) . . ? N4 Cu N2 84.47(10) . . ? N3 Cu N2 115.17(10) . . ? C1 N1 Cu 107.13(18) . . ? C1 N1 H1A 110.3 . . ? Cu N1 H1A 110.3 . . ? C1 N1 H1B 110.3 . . ? Cu N1 H1B 110.3 . . ? H1A N1 H1B 108.5 . . ? C3 N2 Cu 106.36(19) . . ? C3 N2 H2A 110.5 . . ? Cu N2 H2A 110.5 . . ? C3 N2 H2B 110.5 . . ? Cu N2 H2B 110.5 . . ? H2A N2 H2B 108.6 . . ? C5 N3 Cu 108.96(17) . . ? C5 N3 H3A 109.9 . . ? Cu N3 H3A 109.9 . . ? C5 N3 H3B 109.9 . . ? Cu N3 H3B 109.9 . . ? H3A N3 H3B 108.3 . . ? C2 N4 C4 110.8(2) . . ? C2 N4 C6 111.0(2) . . ? C4 N4 C6 112.0(2) . . ? C2 N4 Cu 108.24(18) . . ? C4 N4 Cu 107.98(19) . . ? C6 N4 Cu 106.67(18) . . ? N1 C1 C2 108.3(2) . . ? N1 C1 H1C 110.0 . . ? C2 C1 H1C 110.0 . . ? N1 C1 H1D 110.0 . . ? C2 C1 H1D 110.0 . . ? H1C C1 H1D 108.4 . . ? N4 C2 C1 109.3(2) . . ? N4 C2 H2C 109.8 . . ? C1 C2 H2C 109.8 . . ? N4 C2 H2D 109.8 . . ? C1 C2 H2D 109.8 . . ? H2C C2 H2D 108.3 . . ? N2 C3 C4 109.9(3) . . ? N2 C3 H3C 109.7 . . ? C4 C3 H3C 109.7 . . ? N2 C3 H3D 109.7 . . ? C4 C3 H3D 109.7 . . ? H3C C3 H3D 108.2 . . ? N4 C4 C3 109.7(2) . . ? N4 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? N4 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? N3 C5 C6 108.9(2) . . ? N3 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? N3 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? N4 C6 C5 110.3(2) . . ? N4 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N4 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C11 N5 C7 116.6(3) . . ? C11 N5 Cu 116.0(2) . . ? C7 N5 Cu 125.3(2) . . ? N5 C7 C10 132.8(3) . . ? N5 C7 C8 135.1(3) . . ? C10 C7 C8 92.1(2) . . ? O1 C8 C7 136.2(3) . . ? O1 C8 C9 135.0(3) . . ? C7 C8 C9 88.8(2) . . ? O2 C9 C10 136.1(3) . . ? O2 C9 C8 135.7(3) . . ? C10 C9 C8 88.2(2) . . ? N7 C10 C7 132.2(3) . . ? N7 C10 C9 137.0(3) . . ? C7 C10 C9 90.9(2) . . ? N6 C11 N5 173.4(3) . . ? C10 N7 C12 118.3(3) . . ? N8 C12 N7 172.8(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N8 0.92 2.23 3.002(4) 140.6 2_654 N1 H1B N6 0.92 2.13 2.939(4) 146.5 2_664 N2 H2A O1 0.92 2.40 3.223(4) 148.3 4 N2 H2B N7 0.92 2.12 2.945(3) 148.5 . N3 H3A O1 0.92 2.10 2.943(3) 151.8 2_664 N3 H3B O2 0.92 2.18 2.951(3) 140.8 4 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.92 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.337 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.082 #======END