Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email ELENA.RYBAK-AKIMOVA@TUFTS.EDU _publ_contact_author_name 'Prof Elena Rybak-Akimova' _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_address ; Department of Chemistry Tufts University 62 Talbot Ave Medford MA 02155 UNITED STATES OF AMERICA ; _publ_section_title ; Reactions at the azomethine C=N bonds in the nickel(II) and copper(II) complexes of pyridine-containing Schiff base macrocyclic ligands ; loop_ _publ_author_name 'Elena Rybak-Akimova' 'Charles F. Campana' 'Jeremy S. Disch' 'Terry E. Haas' 'Aida M. Herrera' ; G.V.Kalayda ; 'Ivan V. Korendovych' 'Alexander Y.Nazarenko' 'Richard J.Staples' ; J.P.Wikstrom ; #==END data_NiL5 _database_code_CSD 215949 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H27 Cl2 N5 Ni O9' _chemical_formula_weight 563.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6605(12) _cell_length_b 9.0147(12) _cell_length_c 16.139(2) _cell_angle_alpha 95.823(2) _cell_angle_beta 96.058(2) _cell_angle_gamma 115.9010(10) _cell_volume 1111.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 1.173 _exptl_absorpt_correction_type 'Emprical, SADABS' _exptl_absorpt_correction_T_min 0.620323 _exptl_absorpt_correction_T_max 0.942200 _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an LT-2 low-temperature apparatus operating at 213 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 30 s , such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.75 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing, (1995). The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 6979 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 27.63 _reflns_number_total 4491 _reflns_number_gt 3941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.054, 1998)' _computing_data_reduction 'SAINT (BRUKER, V6.01, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 1998, V5.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.0898P)^2^+0.8856P] 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 4491 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1455 _refine_ls_wR_factor_gt 0.1354 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.67204(5) 0.90914(4) 0.74332(3) 0.03724(15) Uani 1 1 d . . . O9 O 0.2293(3) 0.5424(4) 0.81726(17) 0.0581(7) Uani 1 1 d . . . H9C H 0.2243 0.4752 0.8488 0.087 Uiso 1 1 calc R . . N1 N 0.5571(4) 0.9570(3) 0.83523(17) 0.0423(6) Uani 1 1 d . . . N4 N 0.4587(3) 0.6700(3) 0.73885(16) 0.0374(5) Uani 1 1 d . . . N2 N 0.7744(4) 1.1642(3) 0.7566(2) 0.0480(7) Uani 1 1 d . . . N3 N 0.7036(3) 0.8638(3) 0.62094(18) 0.0411(6) Uani 1 1 d . . . N5 N 0.8838(4) 0.8922(4) 0.7970(2) 0.0517(7) Uani 1 1 d . . . H5C H 0.9795 0.9862 0.7942 0.062 Uiso 1 1 calc R . . H5D H 0.8782 0.8856 0.8520 0.062 Uiso 1 1 calc R . . C10 C 0.4241(5) 0.8327(4) 0.8578(2) 0.0449(7) Uani 1 1 d . . . C11 C 0.3174(5) 0.8634(6) 0.9072(2) 0.0556(9) Uani 1 1 d . . . H11 H 0.2244 0.7762 0.9232 0.067 Uiso 1 1 calc R . . C12 C 0.3533(6) 1.0287(6) 0.9322(2) 0.0625(11) Uani 1 1 d . . . H12 H 0.2843 1.0532 0.9662 0.075 Uiso 1 1 calc R . . C13 C 0.4901(6) 1.1572(5) 0.9073(2) 0.0581(10) Uani 1 1 d . . . H13 H 0.5139 1.2679 0.9239 0.070 Uiso 1 1 calc R . . C1 C 0.5905(5) 1.1177(4) 0.8574(2) 0.0496(8) Uani 1 1 d . . . C9 C 0.4021(4) 0.6604(4) 0.8223(2) 0.0452(7) Uani 1 1 d . . . H9 H 0.4770 0.6312 0.8601 0.054 Uiso 1 1 calc R . . C2 C 0.7248(5) 1.2307(4) 0.8144(3) 0.0534(9) Uani 1 1 d . . . H2 H 0.7716 1.3462 0.8289 0.064 Uiso 1 1 calc R . . C8 C 0.3265(4) 0.6674(4) 0.6709(2) 0.0386(6) Uani 1 1 d . . . H8A H 0.3119 0.7678 0.6828 0.046 Uiso 1 1 calc R . . H8B H 0.2155 0.5720 0.6708 0.046 Uiso 1 1 calc R . . C7 C 0.3776(4) 0.6576(4) 0.5846(2) 0.0413(7) Uani 1 1 d . . . H7A H 0.2769 0.6323 0.5426 0.050 Uiso 1 1 calc R . . H7B H 0.4049 0.5642 0.5765 0.050 Uiso 1 1 calc R . . C6 C 0.5306(4) 0.8118(4) 0.5665(2) 0.0422(7) Uani 1 1 d . . . H6A H 0.5429 0.7910 0.5080 0.051 Uiso 1 1 calc R . . H6B H 0.5023 0.9048 0.5727 0.051 Uiso 1 1 calc R . . C3 C 0.8926(5) 1.2627(4) 0.7024(3) 0.0575(10) Uani 1 1 d . . . H3A H 1.0081 1.2728 0.7194 0.069 Uiso 1 1 calc R . . H3B H 0.9009 1.3742 0.7083 0.069 Uiso 1 1 calc R . . C4 C 0.8256(5) 1.1788(4) 0.6122(3) 0.0571(9) Uani 1 1 d . . . H4A H 0.8912 1.2554 0.5764 0.069 Uiso 1 1 calc R . . H4B H 0.7051 1.1571 0.5985 0.069 Uiso 1 1 calc R . . C5 C 0.8360(5) 1.0139(4) 0.5909(3) 0.0530(8) Uani 1 1 d . . . H5A H 0.8239 0.9881 0.5301 0.064 Uiso 1 1 calc R . . H5B H 0.9512 1.0310 0.6150 0.064 Uiso 1 1 calc R . . C16 C 0.9018(5) 0.7459(5) 0.7568(3) 0.0572(10) Uani 1 1 d . . . H16A H 0.8008 0.6440 0.7615 0.069 Uiso 1 1 calc R . . H16B H 1.0038 0.7439 0.7868 0.069 Uiso 1 1 calc R . . C15 C 0.9185(5) 0.7503(5) 0.6651(3) 0.0596(10) Uani 1 1 d . . . H15A H 0.9497 0.6636 0.6451 0.072 Uiso 1 1 calc R . . H15B H 1.0136 0.8569 0.6608 0.072 Uiso 1 1 calc R . . C14 C 0.7565(5) 0.7268(4) 0.6065(3) 0.0506(8) Uani 1 1 d . . . H14A H 0.7766 0.7163 0.5486 0.061 Uiso 1 1 calc R . . H14B H 0.6602 0.6225 0.6125 0.061 Uiso 1 1 calc R . . Cl1 Cl 0.35326(10) 0.21599(9) 0.67642(6) 0.0477(2) Uani 1 1 d . . . O1 O 0.3747(4) 0.0752(4) 0.6445(2) 0.0768(9) Uani 1 1 d . . . O2 O 0.5180(4) 0.3556(4) 0.7054(3) 0.1057(16) Uani 1 1 d . . . O3 O 0.2562(4) 0.2551(4) 0.61261(18) 0.0605(7) Uani 1 1 d . . . O4 O 0.2561(5) 0.1760(5) 0.7441(2) 0.0816(10) Uani 1 1 d . . . Cl2 Cl 0.15019(13) 0.31851(13) 0.99676(7) 0.0590(3) Uani 1 1 d . . . O5 O 0.1748(9) 0.2817(8) 0.9039(4) 0.0652(15) Uani 0.50 1 d P A 1 O5B O 0.3022(16) 0.4230(16) 0.9718(8) 0.141(4) Uani 0.50 1 d P A 2 O6 O 0.170(2) 0.4765(14) 1.0040(7) 0.152(6) Uani 0.50 1 d P A 1 O6B O 0.1069(13) 0.4231(11) 1.0599(7) 0.105(3) Uani 0.50 1 d P A 2 O7 O 0.2321(9) 0.2551(9) 1.0496(3) 0.143(2) Uani 1 1 d . A . O8 O -0.0064(10) 0.2097(11) 0.9623(7) 0.247(5) Uani 1 1 d . A . H4C H 0.468(5) 0.575(5) 0.724(2) 0.048(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0305(2) 0.0212(2) 0.0542(3) 0.00152(16) -0.00280(16) 0.00952(16) O9 0.0521(14) 0.0514(15) 0.0529(14) 0.0167(11) 0.0060(11) 0.0062(12) N1 0.0417(14) 0.0311(13) 0.0481(14) -0.0016(11) -0.0087(11) 0.0163(11) N4 0.0344(12) 0.0256(12) 0.0463(14) 0.0026(10) -0.0037(10) 0.0111(10) N2 0.0375(14) 0.0231(12) 0.0744(19) 0.0000(12) -0.0074(13) 0.0109(11) N3 0.0333(12) 0.0265(12) 0.0608(16) 0.0066(11) 0.0085(11) 0.0112(10) N5 0.0375(14) 0.0331(14) 0.077(2) 0.0042(13) -0.0094(13) 0.0142(12) C10 0.0488(18) 0.0470(18) 0.0359(15) 0.0018(13) -0.0067(13) 0.0230(15) C11 0.057(2) 0.075(3) 0.0361(16) 0.0083(16) 0.0001(14) 0.032(2) C12 0.078(3) 0.088(3) 0.0371(17) 0.0011(18) -0.0012(17) 0.056(3) C13 0.075(3) 0.061(2) 0.0467(19) -0.0041(17) -0.0099(17) 0.045(2) C1 0.057(2) 0.0409(18) 0.0484(18) -0.0062(14) -0.0141(15) 0.0282(16) C9 0.0421(17) 0.0382(16) 0.0458(17) 0.0091(13) -0.0020(13) 0.0112(14) C2 0.0507(19) 0.0271(15) 0.075(2) -0.0034(15) -0.0134(17) 0.0185(14) C8 0.0303(13) 0.0301(14) 0.0465(16) 0.0063(12) -0.0010(11) 0.0074(11) C7 0.0358(15) 0.0314(15) 0.0472(16) 0.0035(12) -0.0002(12) 0.0087(12) C6 0.0405(16) 0.0354(16) 0.0498(17) 0.0099(13) 0.0077(13) 0.0157(13) C3 0.0384(17) 0.0231(15) 0.101(3) 0.0095(17) 0.0071(18) 0.0064(13) C4 0.0429(18) 0.0343(17) 0.090(3) 0.0240(18) 0.0139(18) 0.0104(15) C5 0.0405(17) 0.0379(17) 0.078(2) 0.0163(16) 0.0170(16) 0.0122(14) C16 0.0405(17) 0.0379(18) 0.094(3) 0.0095(18) -0.0068(17) 0.0226(15) C15 0.0413(18) 0.0424(19) 0.102(3) 0.0090(19) 0.0119(19) 0.0255(16) C14 0.0458(18) 0.0363(17) 0.072(2) 0.0040(15) 0.0108(16) 0.0218(15) Cl1 0.0405(4) 0.0292(4) 0.0712(5) 0.0036(3) 0.0016(3) 0.0164(3) O1 0.076(2) 0.0386(15) 0.122(3) 0.0033(16) 0.0203(19) 0.0331(15) O2 0.0474(16) 0.0345(15) 0.214(5) 0.007(2) -0.030(2) 0.0134(13) O3 0.0543(15) 0.0615(17) 0.0703(17) 0.0248(14) 0.0113(13) 0.0273(13) O4 0.087(2) 0.112(3) 0.0615(18) 0.0215(18) 0.0152(16) 0.058(2) Cl2 0.0584(5) 0.0541(5) 0.0733(6) 0.0218(4) 0.0230(4) 0.0283(4) O5 0.089(4) 0.058(3) 0.050(3) 0.019(3) 0.016(3) 0.032(3) O5B 0.138(9) 0.143(9) 0.185(11) 0.096(9) 0.115(9) 0.067(8) O6 0.299(18) 0.096(7) 0.103(7) -0.001(6) 0.027(9) 0.131(10) O6B 0.119(7) 0.082(6) 0.116(7) -0.009(5) 0.043(6) 0.047(5) O7 0.194(6) 0.223(7) 0.074(3) 0.011(3) -0.002(3) 0.156(6) O8 0.133(6) 0.189(8) 0.332(12) -0.099(8) -0.115(7) 0.058(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 Ni1 N1 1.983(3) . ? Ni1 N5 2.018(3) . ? Ni1 N3 2.047(3) . ? Ni1 N2 2.049(3) . ? Ni1 N4 2.127(3) . ? O9 C9 1.394(4) . ? N1 C10 1.326(5) . ? N1 C1 1.348(4) . ? N4 C9 1.480(4) . ? N4 C8 1.491(4) . ? N2 C2 1.268(5) . ? N2 C3 1.469(5) . ? N3 C14 1.500(4) . ? N3 C6 1.504(4) . ? N3 C5 1.508(4) . ? N5 C16 1.487(5) . ? C10 C11 1.378(5) . ? C10 C9 1.521(5) . ? C11 C12 1.389(6) . ? C12 C13 1.380(7) . ? C13 C1 1.376(6) . ? C1 C2 1.466(6) . ? C8 C7 1.512(5) . ? C7 C6 1.525(4) . ? C3 C4 1.497(6) . ? C4 C5 1.534(5) . ? C16 C15 1.505(6) . ? C15 C14 1.525(5) . ? Cl1 O1 1.415(3) . ? Cl1 O2 1.417(3) . ? Cl1 O4 1.429(4) . ? Cl1 O3 1.429(3) . ? Cl2 O8 1.296(7) . ? Cl2 O6 1.350(9) . ? Cl2 O7 1.372(5) . ? Cl2 O5B 1.374(9) . ? Cl2 O6B 1.504(8) . ? Cl2 O5 1.559(6) . ? 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 Ni1 N5 107.88(13) . . ? N1 Ni1 N3 156.00(11) . . ? N5 Ni1 N3 96.12(13) . . ? N1 Ni1 N2 78.80(12) . . ? N5 Ni1 N2 98.96(11) . . ? N3 Ni1 N2 98.09(12) . . ? N1 Ni1 N4 78.77(11) . . ? N5 Ni1 N4 105.48(11) . . ? N3 Ni1 N4 94.89(10) . . ? N2 Ni1 N4 150.86(11) . . ? C10 N1 C1 121.6(3) . . ? C10 N1 Ni1 119.7(2) . . ? C1 N1 Ni1 116.7(3) . . ? C9 N4 C8 113.0(2) . . ? C9 N4 Ni1 108.84(19) . . ? C8 N4 Ni1 102.49(18) . . ? C2 N2 C3 122.4(3) . . ? C2 N2 Ni1 114.8(3) . . ? C3 N2 Ni1 122.8(2) . . ? C14 N3 C6 109.0(3) . . ? C14 N3 C5 107.0(3) . . ? C6 N3 C5 107.4(3) . . ? C14 N3 Ni1 112.3(2) . . ? C6 N3 Ni1 106.80(19) . . ? C5 N3 Ni1 114.2(2) . . ? C16 N5 Ni1 113.7(2) . . ? N1 C10 C11 121.1(3) . . ? N1 C10 C9 113.6(3) . . ? C11 C10 C9 125.3(4) . . ? C10 C11 C12 117.8(4) . . ? C13 C12 C11 120.7(4) . . ? C1 C13 C12 118.5(4) . . ? N1 C1 C13 120.3(4) . . ? N1 C1 C2 112.1(3) . . ? C13 C1 C2 127.3(3) . . ? O9 C9 N4 112.4(3) . . ? O9 C9 C10 109.7(3) . . ? N4 C9 C10 107.5(3) . . ? N2 C2 C1 117.2(3) . . ? N4 C8 C7 112.2(3) . . ? C8 C7 C6 117.2(3) . . ? N3 C6 C7 116.2(3) . . ? N2 C3 C4 109.7(3) . . ? C3 C4 C5 115.0(3) . . ? N3 C5 C4 116.4(3) . . ? N5 C16 C15 112.3(3) . . ? C16 C15 C14 115.7(3) . . ? N3 C14 C15 115.6(3) . . ? O1 Cl1 O2 110.1(2) . . ? O1 Cl1 O4 108.5(2) . . ? O2 Cl1 O4 110.3(3) . . ? O1 Cl1 O3 110.5(2) . . ? O2 Cl1 O3 109.7(2) . . ? O4 Cl1 O3 107.65(19) . . ? O8 Cl2 O6 112.1(8) . . ? O8 Cl2 O7 113.0(6) . . ? O6 Cl2 O7 127.8(6) . . ? O8 Cl2 O5B 138.3(8) . . ? O6 Cl2 O5B 68.9(9) . . ? O7 Cl2 O5B 93.2(6) . . ? O8 Cl2 O6B 99.1(6) . . ? O6 Cl2 O6B 46.8(6) . . ? O7 Cl2 O6B 100.8(5) . . ? O5B Cl2 O6B 107.5(7) . . ? O8 Cl2 O5 78.7(6) . . ? O6 Cl2 O5 103.0(6) . . ? O7 Cl2 O5 110.4(3) . . ? O5B Cl2 O5 61.5(6) . . ? O6B Cl2 O5 147.0(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 N5 Ni1 N1 C10 -96.7(2) . . . . ? N3 Ni1 N1 C10 82.7(4) . . . . ? N2 Ni1 N1 C10 167.4(3) . . . . ? N4 Ni1 N1 C10 6.1(2) . . . . ? N5 Ni1 N1 C1 99.1(2) . . . . ? N3 Ni1 N1 C1 -81.5(3) . . . . ? N2 Ni1 N1 C1 3.2(2) . . . . ? N4 Ni1 N1 C1 -158.1(2) . . . . ? N1 Ni1 N4 C9 -23.8(2) . . . . ? N5 Ni1 N4 C9 81.8(2) . . . . ? N3 Ni1 N4 C9 179.6(2) . . . . ? N2 Ni1 N4 C9 -64.1(3) . . . . ? N1 Ni1 N4 C8 96.1(2) . . . . ? N5 Ni1 N4 C8 -158.3(2) . . . . ? N3 Ni1 N4 C8 -60.5(2) . . . . ? N2 Ni1 N4 C8 55.8(3) . . . . ? N1 Ni1 N2 C2 1.6(2) . . . . ? N5 Ni1 N2 C2 -105.0(3) . . . . ? N3 Ni1 N2 C2 157.5(2) . . . . ? N4 Ni1 N2 C2 41.9(4) . . . . ? N1 Ni1 N2 C3 -176.9(3) . . . . ? N5 Ni1 N2 C3 76.5(3) . . . . ? N3 Ni1 N2 C3 -21.1(3) . . . . ? N4 Ni1 N2 C3 -136.6(3) . . . . ? N1 Ni1 N3 C14 -137.7(3) . . . . ? N5 Ni1 N3 C14 41.7(2) . . . . ? N2 Ni1 N3 C14 141.7(2) . . . . ? N4 Ni1 N3 C14 -64.5(2) . . . . ? N1 Ni1 N3 C6 -18.3(4) . . . . ? N5 Ni1 N3 C6 161.11(19) . . . . ? N2 Ni1 N3 C6 -98.90(19) . . . . ? N4 Ni1 N3 C6 54.94(19) . . . . ? N1 Ni1 N3 C5 100.3(3) . . . . ? N5 Ni1 N3 C5 -80.3(2) . . . . ? N2 Ni1 N3 C5 19.7(2) . . . . ? N4 Ni1 N3 C5 173.5(2) . . . . ? N1 Ni1 N5 C16 134.2(3) . . . . ? N3 Ni1 N5 C16 -45.6(3) . . . . ? N2 Ni1 N5 C16 -144.8(3) . . . . ? N4 Ni1 N5 C16 51.2(3) . . . . ? C1 N1 C10 C11 -2.0(5) . . . . ? Ni1 N1 C10 C11 -165.4(2) . . . . ? C1 N1 C10 C9 176.6(3) . . . . ? Ni1 N1 C10 C9 13.1(3) . . . . ? N1 C10 C11 C12 0.3(5) . . . . ? C9 C10 C11 C12 -178.1(3) . . . . ? C10 C11 C12 C13 0.8(5) . . . . ? C11 C12 C13 C1 -0.3(5) . . . . ? C10 N1 C1 C13 2.6(5) . . . . ? Ni1 N1 C1 C13 166.5(3) . . . . ? C10 N1 C1 C2 -170.7(3) . . . . ? Ni1 N1 C1 C2 -6.8(3) . . . . ? C12 C13 C1 N1 -1.4(5) . . . . ? C12 C13 C1 C2 170.7(3) . . . . ? C8 N4 C9 O9 43.3(4) . . . . ? Ni1 N4 C9 O9 156.4(2) . . . . ? C8 N4 C9 C10 -77.5(3) . . . . ? Ni1 N4 C9 C10 35.6(3) . . . . ? N1 C10 C9 O9 -155.0(3) . . . . ? C11 C10 C9 O9 23.4(4) . . . . ? N1 C10 C9 N4 -32.6(3) . . . . ? C11 C10 C9 N4 145.9(3) . . . . ? C3 N2 C2 C1 172.8(3) . . . . ? Ni1 N2 C2 C1 -5.8(4) . . . . ? N1 C1 C2 N2 8.3(4) . . . . ? C13 C1 C2 N2 -164.4(3) . . . . ? C9 N4 C8 C7 -173.5(3) . . . . ? Ni1 N4 C8 C7 69.5(3) . . . . ? N4 C8 C7 C6 -69.9(4) . . . . ? C14 N3 C6 C7 62.8(4) . . . . ? C5 N3 C6 C7 178.3(3) . . . . ? Ni1 N3 C6 C7 -58.8(3) . . . . ? C8 C7 C6 N3 62.4(4) . . . . ? C2 N2 C3 C4 -134.4(3) . . . . ? Ni1 N2 C3 C4 44.0(4) . . . . ? N2 C3 C4 C5 -69.5(4) . . . . ? C14 N3 C5 C4 -170.6(3) . . . . ? C6 N3 C5 C4 72.5(4) . . . . ? Ni1 N3 C5 C4 -45.7(4) . . . . ? C3 C4 C5 N3 75.1(4) . . . . ? Ni1 N5 C16 C15 60.6(4) . . . . ? N5 C16 C15 C14 -67.9(4) . . . . ? C6 N3 C14 C15 -172.6(3) . . . . ? C5 N3 C14 C15 71.5(4) . . . . ? Ni1 N3 C14 C15 -54.5(4) . . . . ? C16 C15 C14 N3 66.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.866 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.866 _refine_diff_density_max 0.772 _refine_diff_density_min -0.599 _refine_diff_density_rms 0.093 #---------------------------------------------------------- #==END data_NiL5CH3CN _database_code_CSD 215950 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H30 Cl2 N6 Ni O9' _chemical_formula_weight 604.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 12.9303(7) _cell_length_b 11.8558(7) _cell_length_c 16.8216(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.8960(10) _cell_angle_gamma 90.00 _cell_volume 2547.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 1.030 _exptl_absorpt_correction_type 'empirical, sadabs' _exptl_absorpt_correction_T_min 0.7015 _exptl_absorpt_correction_T_max 0.9422 _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an LT-2 low-temperature apparatus operating at 213 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 30 s , such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.75 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing, (1995). The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. ; _diffrn_ambient_temperature 213(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 ? _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 15696 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.73 _reflns_number_total 5402 _reflns_number_gt 4798 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.054, 1998)' _computing_data_reduction 'SAINT (BRUKER, V6.01, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 1998, V5.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.0606P)^2^+1.2875P] 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 5402 _refine_ls_number_parameters 338 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.1046 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.262803(19) 0.78114(2) 0.007156(15) 0.02736(10) Uani 1 1 d . . . N1 N 0.20188(14) 0.89156(15) 0.07474(11) 0.0341(4) Uani 1 1 d . . . N2 N 0.10358(15) 0.74940(18) -0.02478(12) 0.0397(4) Uani 1 1 d . . . N4 N 0.39693(14) 0.81984(15) 0.09294(10) 0.0302(4) Uani 1 1 d . . . H4C H 0.4560 0.8215 0.0687 0.036 Uiso 1 1 calc R . . N5 N 0.28989(15) 0.87293(16) -0.08837(11) 0.0354(4) Uani 1 1 d . . . H5A H 0.2365 0.8610 -0.1295 0.042 Uiso 1 1 calc R . . H5B H 0.2890 0.9473 -0.0751 0.042 Uiso 1 1 calc R . . N3 N 0.31668(15) 0.63029(15) -0.02694(10) 0.0337(4) Uani 1 1 d . . . O9 O 0.42920(14) 0.94899(17) 0.20750(10) 0.0477(4) Uani 1 1 d . . . H9C H 0.4919 0.9317 0.2106 0.071 Uiso 1 1 calc R . . C10 C 0.26328(18) 0.94925(18) 0.12959(13) 0.0359(5) Uani 1 1 d . . . C11 C 0.2207(2) 1.0194(2) 0.18324(17) 0.0480(6) Uani 1 1 d . . . H11 H 0.2642 1.0614 0.2224 0.058 Uiso 1 1 calc R . . C12 C 0.1142(2) 1.0249(2) 0.17695(19) 0.0552(7) Uani 1 1 d . . . H12 H 0.0841 1.0728 0.2116 0.066 Uiso 1 1 calc R . . C13 C 0.0496(2) 0.9612(2) 0.12026(18) 0.0513(6) Uani 1 1 d . . . H13 H -0.0237 0.9643 0.1165 0.062 Uiso 1 1 calc R . . C1 C 0.09660(18) 0.8931(2) 0.06966(15) 0.0397(5) Uani 1 1 d . . . C9 C 0.37887(18) 0.93284(19) 0.12873(13) 0.0355(5) Uani 1 1 d . . . H9 H 0.4029 0.9920 0.0943 0.043 Uiso 1 1 calc R . . C2 C 0.04544(19) 0.8099(2) 0.01228(16) 0.0440(6) Uani 1 1 d . . . H2 H -0.0277 0.8016 0.0032 0.053 Uiso 1 1 calc R . . C3 C 0.0605(2) 0.6573(2) -0.07694(17) 0.0521(6) Uani 1 1 d . . . H3A H 0.0575 0.6794 -0.1334 0.063 Uiso 1 1 calc R . . H3B H -0.0108 0.6405 -0.0676 0.063 Uiso 1 1 calc R . . C4 C 0.1287(2) 0.5529(2) -0.05988(18) 0.0543(7) Uani 1 1 d . . . H4A H 0.0930 0.4890 -0.0891 0.065 Uiso 1 1 calc R . . H4B H 0.1361 0.5358 -0.0023 0.065 Uiso 1 1 calc R . . C5 C 0.2375(2) 0.5642(2) -0.08327(15) 0.0490(6) Uani 1 1 d . . . H5C H 0.2654 0.4882 -0.0885 0.059 Uiso 1 1 calc R . . H5D H 0.2302 0.5997 -0.1365 0.059 Uiso 1 1 calc R . . C14 C 0.4115(2) 0.6443(2) -0.06723(14) 0.0423(5) Uani 1 1 d . . . H14A H 0.4307 0.5701 -0.0862 0.051 Uiso 1 1 calc R . . H14B H 0.4696 0.6698 -0.0268 0.051 Uiso 1 1 calc R . . C15 C 0.4008(2) 0.7255(2) -0.13762(14) 0.0463(6) Uani 1 1 d . . . H15A H 0.4624 0.7170 -0.1646 0.056 Uiso 1 1 calc R . . H15B H 0.3394 0.7034 -0.1762 0.056 Uiso 1 1 calc R . . C16 C 0.39006(19) 0.8482(2) -0.11751(14) 0.0412(5) Uani 1 1 d . . . H16A H 0.4484 0.8700 -0.0760 0.049 Uiso 1 1 calc R . . H16B H 0.3944 0.8937 -0.1655 0.049 Uiso 1 1 calc R . . C6 C 0.3463(2) 0.56227(18) 0.04842(13) 0.0391(5) Uani 1 1 d . . . H6A H 0.3717 0.4886 0.0334 0.047 Uiso 1 1 calc R . . H6B H 0.2830 0.5490 0.0724 0.047 Uiso 1 1 calc R . . C7 C 0.42932(18) 0.61404(19) 0.11269(13) 0.0377(5) Uani 1 1 d . . . H7A H 0.4467 0.5583 0.1557 0.045 Uiso 1 1 calc R . . H7B H 0.4927 0.6265 0.0886 0.045 Uiso 1 1 calc R . . C8 C 0.40223(18) 0.72432(18) 0.15096(12) 0.0350(5) Uani 1 1 d . . . H8A H 0.3346 0.7165 0.1698 0.042 Uiso 1 1 calc R . . H8B H 0.4553 0.7407 0.1977 0.042 Uiso 1 1 calc R . . Cl1 Cl 0.69454(6) 0.80788(6) 0.02455(5) 0.05756(19) Uani 1 1 d . . . O1 O 0.6876(3) 0.7171(2) 0.0779(2) 0.1080(11) Uani 1 1 d . . . O2 O 0.6816(4) 0.7743(3) -0.0558(2) 0.1275(14) Uani 1 1 d . . . O3 O 0.78708(18) 0.8719(2) 0.0467(2) 0.0965(9) Uani 1 1 d . . . O4 O 0.60853(16) 0.8844(2) 0.03252(14) 0.0675(6) Uani 1 1 d . . . Cl2 Cl 0.10095(4) 0.65533(5) 0.20976(3) 0.03882(14) Uani 1 1 d . . . O5 O 0.10635(17) 0.5791(2) 0.27613(14) 0.0735(7) Uani 1 1 d . . . O6 O 0.1417(2) 0.6043(3) 0.14522(15) 0.0971(9) Uani 1 1 d . . . O7 O 0.1662(2) 0.7502(2) 0.23578(16) 0.0815(7) Uani 1 1 d . . . O8 O -0.00328(16) 0.6890(2) 0.18267(16) 0.0718(6) Uani 1 1 d . . . N1S N 0.6405(2) 0.9093(3) 0.24177(19) 0.0807(9) Uani 1 1 d . . . C2S C 0.7193(3) 0.8703(3) 0.2536(2) 0.0636(8) Uani 1 1 d . . . C1S C 0.8219(3) 0.8204(4) 0.2673(5) 0.105(2) Uani 1 1 d . . . H1SA H 0.868(4) 0.869(5) 0.271(3) 0.121(18) Uiso 1 1 d . . . H1SB H 0.819(8) 0.775(8) 0.203(6) 0.26(5) Uiso 1 1 d . . . H1SC H 0.840(3) 0.773(4) 0.321(3) 0.098(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.02571(15) 0.02823(15) 0.02853(15) 0.00058(10) 0.00543(10) 0.00416(10) N1 0.0314(9) 0.0330(9) 0.0395(10) 0.0018(8) 0.0103(7) 0.0065(7) N2 0.0312(10) 0.0435(10) 0.0434(11) 0.0054(8) 0.0024(8) -0.0011(8) N4 0.0291(9) 0.0359(9) 0.0270(8) -0.0009(7) 0.0084(7) 0.0023(7) N5 0.0391(10) 0.0336(9) 0.0328(9) 0.0045(7) 0.0038(7) 0.0030(8) N3 0.0414(10) 0.0290(8) 0.0300(9) -0.0005(7) 0.0032(7) 0.0056(7) O9 0.0458(10) 0.0589(11) 0.0372(8) -0.0123(8) 0.0029(7) -0.0030(9) C10 0.0392(12) 0.0322(10) 0.0383(11) 0.0016(9) 0.0123(9) 0.0020(9) C11 0.0521(15) 0.0391(12) 0.0565(15) -0.0104(11) 0.0201(12) -0.0002(11) C12 0.0560(16) 0.0460(14) 0.0703(18) -0.0095(13) 0.0309(14) 0.0092(12) C13 0.0377(13) 0.0489(14) 0.0719(18) 0.0030(13) 0.0230(12) 0.0122(11) C1 0.0317(11) 0.0405(12) 0.0490(13) 0.0086(10) 0.0127(9) 0.0095(9) C9 0.0379(12) 0.0348(11) 0.0339(11) -0.0041(9) 0.0062(9) -0.0016(9) C2 0.0283(11) 0.0507(13) 0.0524(14) 0.0094(11) 0.0047(10) 0.0029(10) C3 0.0405(14) 0.0599(16) 0.0526(15) -0.0046(12) -0.0034(11) -0.0119(12) C4 0.0598(17) 0.0435(14) 0.0553(15) -0.0047(12) -0.0049(13) -0.0147(12) C5 0.0636(16) 0.0377(12) 0.0431(13) -0.0097(10) 0.0001(12) 0.0002(11) C14 0.0489(14) 0.0453(13) 0.0346(11) -0.0012(10) 0.0124(10) 0.0179(11) C15 0.0514(15) 0.0601(16) 0.0294(11) -0.0001(10) 0.0124(10) 0.0107(12) C16 0.0417(13) 0.0519(14) 0.0315(11) 0.0080(10) 0.0101(9) -0.0009(10) C6 0.0503(13) 0.0294(10) 0.0376(11) 0.0040(9) 0.0066(10) 0.0066(10) C7 0.0416(12) 0.0405(12) 0.0313(10) 0.0083(9) 0.0068(9) 0.0136(10) C8 0.0378(11) 0.0420(12) 0.0259(10) 0.0035(8) 0.0071(8) 0.0045(9) Cl1 0.0531(4) 0.0420(3) 0.0781(5) -0.0023(3) 0.0116(3) -0.0068(3) O1 0.140(3) 0.0478(14) 0.142(3) 0.0227(15) 0.040(2) 0.0006(15) O2 0.165(4) 0.108(3) 0.125(3) -0.049(2) 0.070(3) -0.021(2) O3 0.0442(12) 0.0730(16) 0.172(3) -0.0051(18) 0.0151(15) -0.0109(12) O4 0.0480(11) 0.0741(14) 0.0795(15) 0.0071(12) 0.0074(10) 0.0053(10) Cl2 0.0296(3) 0.0498(3) 0.0375(3) 0.0046(2) 0.0065(2) -0.0028(2) O5 0.0527(12) 0.0933(17) 0.0733(14) 0.0400(13) 0.0058(10) -0.0105(11) O6 0.095(2) 0.136(3) 0.0654(15) -0.0169(16) 0.0283(14) 0.0314(18) O7 0.0728(16) 0.0792(15) 0.0867(17) 0.0052(13) -0.0054(13) -0.0334(13) O8 0.0340(10) 0.0799(15) 0.0991(18) 0.0235(13) 0.0034(10) 0.0064(10) N1S 0.0582(17) 0.096(2) 0.082(2) -0.0050(17) -0.0057(14) 0.0226(16) C2S 0.0527(17) 0.0590(17) 0.074(2) -0.0004(15) -0.0056(14) 0.0065(14) C1S 0.050(2) 0.064(2) 0.192(6) 0.027(3) -0.012(3) 0.0097(18) _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 N1 1.9758(18) . ? Ni1 N5 2.0157(18) . ? Ni1 N3 2.0338(18) . ? Ni1 N2 2.0801(19) . ? Ni1 N4 2.1277(17) . ? N1 C10 1.313(3) . ? N1 C1 1.351(3) . ? N2 C2 1.270(3) . ? N2 C3 1.457(3) . ? N4 C8 1.490(3) . ? N4 C9 1.502(3) . ? N5 C16 1.483(3) . ? N3 C14 1.499(3) . ? N3 C6 1.501(3) . ? N3 C5 1.504(3) . ? O9 C9 1.396(3) . ? C10 C11 1.401(3) . ? C10 C9 1.510(3) . ? C11 C12 1.366(4) . ? C12 C13 1.390(4) . ? C13 C1 1.380(3) . ? C1 C2 1.464(4) . ? C3 C4 1.520(4) . ? C4 C5 1.524(4) . ? C14 C15 1.516(3) . ? C15 C16 1.505(4) . ? C6 C7 1.529(3) . ? C7 C8 1.522(3) . ? Cl1 O2 1.394(4) . ? Cl1 O1 1.413(3) . ? Cl1 O3 1.417(2) . ? Cl1 O4 1.458(2) . ? Cl2 O8 1.412(2) . ? Cl2 O6 1.414(2) . ? Cl2 O5 1.430(2) . ? Cl2 O7 1.433(2) . ? N1S C2S 1.110(4) . ? C2S C1S 1.438(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 N1 Ni1 N5 103.59(8) . . ? N1 Ni1 N3 158.33(8) . . ? N5 Ni1 N3 98.08(7) . . ? N1 Ni1 N2 78.56(8) . . ? N5 Ni1 N2 100.30(8) . . ? N3 Ni1 N2 97.85(8) . . ? N1 Ni1 N4 79.78(7) . . ? N5 Ni1 N4 101.56(7) . . ? N3 Ni1 N4 95.86(7) . . ? N2 Ni1 N4 152.20(8) . . ? C10 N1 C1 122.1(2) . . ? C10 N1 Ni1 119.88(15) . . ? C1 N1 Ni1 117.40(16) . . ? C2 N2 C3 121.3(2) . . ? C2 N2 Ni1 114.10(17) . . ? C3 N2 Ni1 124.19(17) . . ? C8 N4 C9 114.19(16) . . ? C8 N4 Ni1 103.32(13) . . ? C9 N4 Ni1 107.65(13) . . ? C16 N5 Ni1 115.16(13) . . ? C14 N3 C6 108.74(17) . . ? C14 N3 C5 107.33(18) . . ? C6 N3 C5 108.18(18) . . ? C14 N3 Ni1 111.72(14) . . ? C6 N3 Ni1 106.74(13) . . ? C5 N3 Ni1 113.97(15) . . ? N1 C10 C11 120.5(2) . . ? N1 C10 C9 114.72(19) . . ? C11 C10 C9 124.8(2) . . ? C12 C11 C10 118.1(3) . . ? C11 C12 C13 121.3(2) . . ? C1 C13 C12 117.7(2) . . ? N1 C1 C13 120.3(2) . . ? N1 C1 C2 112.4(2) . . ? C13 C1 C2 127.1(2) . . ? O9 C9 N4 115.10(18) . . ? O9 C9 C10 106.87(18) . . ? N4 C9 C10 109.54(18) . . ? N2 C2 C1 117.6(2) . . ? N2 C3 C4 109.9(2) . . ? C3 C4 C5 114.3(2) . . ? N3 C5 C4 116.7(2) . . ? N3 C14 C15 116.17(19) . . ? C16 C15 C14 116.04(19) . . ? N5 C16 C15 112.4(2) . . ? N3 C6 C7 116.15(19) . . ? C8 C7 C6 117.49(19) . . ? N4 C8 C7 111.48(17) . . ? O2 Cl1 O1 112.8(2) . . ? O2 Cl1 O3 112.2(2) . . ? O1 Cl1 O3 112.1(2) . . ? O2 Cl1 O4 106.7(2) . . ? O1 Cl1 O4 106.95(18) . . ? O3 Cl1 O4 105.54(15) . . ? O8 Cl2 O6 108.89(17) . . ? O8 Cl2 O5 111.09(14) . . ? O6 Cl2 O5 110.49(18) . . ? O8 Cl2 O7 111.34(16) . . ? O6 Cl2 O7 107.40(19) . . ? O5 Cl2 O7 107.57(15) . . ? N1S C2S C1S 178.8(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 N5 Ni1 N1 C10 -90.09(17) . . . . ? N3 Ni1 N1 C10 89.5(3) . . . . ? N2 Ni1 N1 C10 171.93(18) . . . . ? N4 Ni1 N1 C10 9.46(17) . . . . ? N5 Ni1 N1 C1 98.78(17) . . . . ? N3 Ni1 N1 C1 -81.6(3) . . . . ? N2 Ni1 N1 C1 0.80(16) . . . . ? N4 Ni1 N1 C1 -161.67(17) . . . . ? N1 Ni1 N2 C2 -1.07(17) . . . . ? N5 Ni1 N2 C2 -103.01(18) . . . . ? N3 Ni1 N2 C2 157.25(18) . . . . ? N4 Ni1 N2 C2 38.4(3) . . . . ? N1 Ni1 N2 C3 -173.6(2) . . . . ? N5 Ni1 N2 C3 84.5(2) . . . . ? N3 Ni1 N2 C3 -15.3(2) . . . . ? N4 Ni1 N2 C3 -134.1(2) . . . . ? N1 Ni1 N4 C8 98.99(13) . . . . ? N5 Ni1 N4 C8 -159.08(12) . . . . ? N3 Ni1 N4 C8 -59.56(13) . . . . ? N2 Ni1 N4 C8 59.7(2) . . . . ? N1 Ni1 N4 C9 -22.16(13) . . . . ? N5 Ni1 N4 C9 79.77(14) . . . . ? N3 Ni1 N4 C9 179.28(13) . . . . ? N2 Ni1 N4 C9 -61.4(2) . . . . ? N1 Ni1 N5 C16 139.33(16) . . . . ? N3 Ni1 N5 C16 -40.51(17) . . . . ? N2 Ni1 N5 C16 -140.07(16) . . . . ? N4 Ni1 N5 C16 57.20(17) . . . . ? N1 Ni1 N3 C14 -141.8(2) . . . . ? N5 Ni1 N3 C14 37.76(15) . . . . ? N2 Ni1 N3 C14 139.41(14) . . . . ? N4 Ni1 N3 C14 -64.83(14) . . . . ? N1 Ni1 N3 C6 -23.1(3) . . . . ? N5 Ni1 N3 C6 156.51(15) . . . . ? N2 Ni1 N3 C6 -101.84(15) . . . . ? N4 Ni1 N3 C6 53.92(15) . . . . ? N1 Ni1 N3 C5 96.3(2) . . . . ? N5 Ni1 N3 C5 -84.12(17) . . . . ? N2 Ni1 N3 C5 17.53(17) . . . . ? N4 Ni1 N3 C5 173.29(16) . . . . ? C1 N1 C10 C11 -2.9(3) . . . . ? Ni1 N1 C10 C11 -173.61(18) . . . . ? C1 N1 C10 C9 177.1(2) . . . . ? Ni1 N1 C10 C9 6.4(3) . . . . ? N1 C10 C11 C12 0.5(4) . . . . ? C9 C10 C11 C12 -179.5(2) . . . . ? C10 C11 C12 C13 1.4(4) . . . . ? C11 C12 C13 C1 -0.9(4) . . . . ? C10 N1 C1 C13 3.4(3) . . . . ? Ni1 N1 C1 C13 174.34(18) . . . . ? C10 N1 C1 C2 -171.4(2) . . . . ? Ni1 N1 C1 C2 -0.5(3) . . . . ? C12 C13 C1 N1 -1.5(4) . . . . ? C12 C13 C1 C2 172.5(2) . . . . ? C8 N4 C9 O9 37.1(3) . . . . ? Ni1 N4 C9 O9 151.19(15) . . . . ? C8 N4 C9 C10 -83.3(2) . . . . ? Ni1 N4 C9 C10 30.77(19) . . . . ? N1 C10 C9 O9 -150.93(19) . . . . ? C11 C10 C9 O9 29.1(3) . . . . ? N1 C10 C9 N4 -25.6(3) . . . . ? C11 C10 C9 N4 154.4(2) . . . . ? C3 N2 C2 C1 173.9(2) . . . . ? Ni1 N2 C2 C1 1.2(3) . . . . ? N1 C1 C2 N2 -0.5(3) . . . . ? C13 C1 C2 N2 -174.9(2) . . . . ? C2 N2 C3 C4 -134.2(3) . . . . ? Ni1 N2 C3 C4 37.8(3) . . . . ? N2 C3 C4 C5 -67.2(3) . . . . ? C14 N3 C5 C4 -172.1(2) . . . . ? C6 N3 C5 C4 70.7(3) . . . . ? Ni1 N3 C5 C4 -47.8(3) . . . . ? C3 C4 C5 N3 77.9(3) . . . . ? C6 N3 C14 C15 -171.1(2) . . . . ? C5 N3 C14 C15 72.1(3) . . . . ? Ni1 N3 C14 C15 -53.5(2) . . . . ? N3 C14 C15 C16 68.2(3) . . . . ? Ni1 N5 C16 C15 55.7(2) . . . . ? C14 C15 C16 N5 -67.3(3) . . . . ? C14 N3 C6 C7 61.9(2) . . . . ? C5 N3 C6 C7 178.2(2) . . . . ? Ni1 N3 C6 C7 -58.8(2) . . . . ? N3 C6 C7 C8 63.7(3) . . . . ? C9 N4 C8 C7 -175.42(18) . . . . ? Ni1 N4 C8 C7 67.96(19) . . . . ? C6 C7 C8 N4 -69.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 27.73 _diffrn_measured_fraction_theta_full 0.902 _refine_diff_density_max 0.665 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.062 #------------------------------------------------------------- #==END data_CuL5 _database_code_CSD 215951 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H27 Cl2 Cu N5 O9' _chemical_formula_weight 567.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6896(4) _cell_length_b 9.0740(5) _cell_length_c 16.1316(8) _cell_angle_alpha 96.6400(10) _cell_angle_beta 95.6530(10) _cell_angle_gamma 116.1710(10) _cell_volume 1117.85(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description chunk _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 586 _exptl_absorpt_coefficient_mu 1.275 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an LT-2 low-temperature apparatus operating at 213 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 30 s, such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.75 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing, (1995). The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 7364 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 28.30 _reflns_number_total 5154 _reflns_number_gt 4589 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.054, 1998)' _computing_data_reduction 'SAINT (BRUKER, V6.01, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 1998, V5.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.1011P)^2^+1.2379P] 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 5154 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1631 _refine_ls_wR_factor_gt 0.1574 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.66762(5) 0.90942(4) 0.74510(2) 0.03103(14) Uani 1 1 d . . . N3 N 0.6981(4) 0.8630(3) 0.62322(17) 0.0345(5) Uani 1 1 d . . . N4 N 0.4557(3) 0.6726(3) 0.73661(17) 0.0336(5) Uani 1 1 d . . . H4C H 0.4868 0.5913 0.7209 0.040 Uiso 1 1 calc R . . N2 N 0.7647(4) 1.1613(3) 0.7569(2) 0.0405(6) Uani 1 1 d . . . N5 N 0.8927(4) 0.8898(4) 0.7991(2) 0.0425(6) Uani 1 1 d . . . H5C H 0.9890 0.9824 0.7955 0.051 Uiso 1 1 calc R . . H5D H 0.8897 0.8840 0.8543 0.051 Uiso 1 1 calc R . . N1 N 0.5501(4) 0.9553(4) 0.83449(17) 0.0376(6) Uani 1 1 d . . . C6 C 0.5271(4) 0.8141(4) 0.5684(2) 0.0386(7) Uani 1 1 d . . . H6A H 0.5409 0.7962 0.5097 0.046 Uiso 1 1 calc R . . H6B H 0.5004 0.9074 0.5766 0.046 Uiso 1 1 calc R . . C7 C 0.3716(4) 0.6593(4) 0.5832(2) 0.0400(7) Uani 1 1 d . . . H7A H 0.2721 0.6376 0.5416 0.048 Uiso 1 1 calc R . . H7B H 0.3963 0.5652 0.5725 0.048 Uiso 1 1 calc R . . C8 C 0.3200(4) 0.6653(4) 0.6701(2) 0.0369(7) Uani 1 1 d . . . H8A H 0.3014 0.7626 0.6833 0.044 Uiso 1 1 calc R . . H8B H 0.2114 0.5670 0.6696 0.044 Uiso 1 1 calc R . . C5 C 0.8348(5) 1.0117(5) 0.5945(3) 0.0448(8) Uani 1 1 d . . . H5A H 0.8275 0.9837 0.5339 0.054 Uiso 1 1 calc R . . H5B H 0.9482 1.0295 0.6211 0.054 Uiso 1 1 calc R . . C4 C 0.8253(5) 1.1755(5) 0.6128(3) 0.0490(9) Uani 1 1 d . . . H4A H 0.8962 1.2511 0.5784 0.059 Uiso 1 1 calc R . . H4B H 0.7061 1.1545 0.5961 0.059 Uiso 1 1 calc R . . C3 C 0.8857(5) 1.2603(4) 0.7052(3) 0.0520(9) Uani 1 1 d . . . H3A H 1.0009 1.2727 0.7243 0.062 Uiso 1 1 calc R . . H3B H 0.8923 1.3707 0.7111 0.062 Uiso 1 1 calc R . . C14 C 0.7469(5) 0.7233(4) 0.6080(2) 0.0421(7) Uani 1 1 d . . . H14A H 0.7604 0.7077 0.5491 0.051 Uiso 1 1 calc R . . H14B H 0.6505 0.6215 0.6163 0.051 Uiso 1 1 calc R . . C15 C 0.9110(5) 0.7446(5) 0.6625(3) 0.0485(8) Uani 1 1 d . . . H15A H 1.0063 0.8498 0.6571 0.058 Uiso 1 1 calc R . . H15B H 0.9379 0.6564 0.6401 0.058 Uiso 1 1 calc R . . C16 C 0.9029(5) 0.7419(5) 0.7562(3) 0.0471(8) Uani 1 1 d . . . H16A H 0.8019 0.6417 0.7624 0.056 Uiso 1 1 calc R . . H16B H 1.0056 0.7383 0.7834 0.056 Uiso 1 1 calc R . . C9 C 0.4014(5) 0.6605(4) 0.8213(2) 0.0413(7) Uani 1 1 d . . . H9 H 0.4786 0.6337 0.8581 0.050 Uiso 1 1 calc R . . C10 C 0.4199(5) 0.8307(5) 0.8580(2) 0.0418(7) Uani 1 1 d . . . C11 C 0.3123(6) 0.8594(6) 0.9086(2) 0.0545(10) Uani 1 1 d . . . H11 H 0.2215 0.7713 0.9249 0.065 Uiso 1 1 calc R . . C12 C 0.3435(6) 1.0215(7) 0.9340(2) 0.0597(11) Uani 1 1 d . . . H12 H 0.2734 1.0440 0.9681 0.072 Uiso 1 1 calc R . . C13 C 0.4800(6) 1.1522(6) 0.9087(2) 0.0563(11) Uani 1 1 d . . . H13 H 0.5023 1.2622 0.9257 0.068 Uiso 1 1 calc R . . C1 C 0.5810(5) 1.1146(5) 0.8579(2) 0.0440(8) Uani 1 1 d . . . C2 C 0.7146(5) 1.2282(4) 0.8145(2) 0.0468(8) Uani 1 1 d . . . H2 H 0.7600 1.3435 0.8288 0.056 Uiso 1 1 calc R . . O9 O 0.2302(4) 0.5405(4) 0.8164(2) 0.0613(8) Uani 1 1 d . . . H9C H 0.2259 0.4789 0.8504 0.092 Uiso 1 1 calc R . . Cl1 Cl 0.35006(11) 0.21950(10) 0.67396(6) 0.0423(2) Uani 1 1 d . . . O1 O 0.3651(5) 0.0767(4) 0.6385(3) 0.0774(10) Uani 1 1 d . . . O2 O 0.2522(4) 0.2611(4) 0.6125(2) 0.0589(7) Uani 1 1 d . . . O3 O 0.5162(5) 0.3577(4) 0.7017(4) 0.1015(17) Uani 1 1 d . . . O4 O 0.2564(6) 0.1790(6) 0.7429(2) 0.0832(11) Uani 1 1 d . . . Cl2 Cl 0.15115(14) 0.32282(14) 0.99579(7) 0.0556(3) Uani 1 1 d . . . O5 O 0.0000(12) 0.2165(14) 0.9558(8) 0.257(6) Uani 1 1 d . . . O6 O 0.2412(17) 0.3508(19) 0.9326(9) 0.330(10) Uani 1 1 d . . . O7 O 0.2317(11) 0.2573(11) 1.0491(4) 0.161(3) Uani 1 1 d . . . O8 O 0.1335(16) 0.4421(12) 1.0393(8) 0.275(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0294(2) 0.0248(2) 0.0359(2) 0.00484(14) 0.00231(14) 0.01044(15) N3 0.0339(13) 0.0305(13) 0.0383(13) 0.0091(10) 0.0075(10) 0.0129(11) N4 0.0300(12) 0.0290(12) 0.0377(13) 0.0083(10) 0.0027(10) 0.0100(10) N2 0.0378(14) 0.0274(13) 0.0509(16) 0.0040(11) -0.0029(12) 0.0128(11) N5 0.0348(14) 0.0387(15) 0.0486(16) 0.0057(12) -0.0038(12) 0.0146(12) N1 0.0385(14) 0.0405(15) 0.0332(13) 0.0040(11) 0.0005(10) 0.0191(12) C6 0.0400(17) 0.0369(16) 0.0361(15) 0.0091(12) 0.0050(13) 0.0147(14) C7 0.0363(16) 0.0390(17) 0.0345(15) 0.0054(12) -0.0011(12) 0.0099(13) C8 0.0290(14) 0.0352(16) 0.0386(16) 0.0094(12) 0.0020(12) 0.0077(12) C5 0.0386(17) 0.0404(18) 0.052(2) 0.0161(15) 0.0139(15) 0.0120(14) C4 0.0402(18) 0.0384(18) 0.065(2) 0.0240(17) 0.0108(16) 0.0113(15) C3 0.0421(19) 0.0273(16) 0.079(3) 0.0123(16) 0.0079(18) 0.0093(14) C14 0.0457(19) 0.0377(17) 0.0449(18) 0.0057(13) 0.0106(14) 0.0207(15) C15 0.0416(19) 0.0448(19) 0.066(2) 0.0076(17) 0.0108(17) 0.0257(16) C16 0.0393(18) 0.0418(18) 0.062(2) 0.0101(16) -0.0019(16) 0.0226(15) C9 0.0371(17) 0.0417(18) 0.0391(16) 0.0140(13) 0.0032(13) 0.0116(14) C10 0.0406(17) 0.055(2) 0.0309(15) 0.0088(14) 0.0012(13) 0.0233(15) C11 0.049(2) 0.088(3) 0.0330(17) 0.0138(18) 0.0062(15) 0.037(2) C12 0.064(3) 0.095(3) 0.0368(18) 0.004(2) 0.0045(17) 0.054(3) C13 0.072(3) 0.071(3) 0.0379(18) -0.0033(17) -0.0051(18) 0.049(2) C1 0.054(2) 0.0462(19) 0.0343(16) -0.0021(13) -0.0059(14) 0.0302(17) C2 0.055(2) 0.0310(16) 0.0498(19) -0.0024(14) -0.0098(16) 0.0213(15) O9 0.0496(16) 0.0592(18) 0.0558(17) 0.0239(14) 0.0108(13) 0.0043(13) Cl1 0.0407(4) 0.0340(4) 0.0535(5) 0.0093(3) 0.0070(3) 0.0181(3) O1 0.084(3) 0.0500(18) 0.107(3) 0.0051(18) 0.023(2) 0.0401(18) O2 0.0560(17) 0.0645(19) 0.0620(18) 0.0274(15) 0.0114(14) 0.0287(15) O3 0.0481(19) 0.0411(17) 0.194(5) 0.021(2) -0.023(2) 0.0104(15) O4 0.090(3) 0.119(3) 0.059(2) 0.034(2) 0.0246(19) 0.058(3) Cl2 0.0569(6) 0.0556(6) 0.0601(6) 0.0168(4) 0.0217(5) 0.0268(5) O5 0.127(7) 0.228(11) 0.288(13) -0.109(10) -0.062(8) 0.023(7) O6 0.393(16) 0.52(2) 0.441(17) 0.440(18) 0.369(15) 0.389(17) O7 0.227(8) 0.273(9) 0.082(3) 0.071(5) 0.050(4) 0.187(8) O8 0.285(13) 0.180(8) 0.337(14) -0.151(9) -0.113(11) 0.167(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.955(3) . ? Cu1 N3 2.030(3) . ? Cu1 N2 2.034(3) . ? Cu1 N4 2.102(3) . ? Cu1 N5 2.150(3) . ? N3 C6 1.502(4) . ? N3 C14 1.507(4) . ? N3 C5 1.512(4) . ? N4 C8 1.488(4) . ? N4 C9 1.489(4) . ? N2 C2 1.267(5) . ? N2 C3 1.457(5) . ? N5 C16 1.480(5) . ? N1 C10 1.325(5) . ? N1 C1 1.348(5) . ? C6 C7 1.524(5) . ? C7 C8 1.515(5) . ? C5 C4 1.522(5) . ? C4 C3 1.520(6) . ? C14 C15 1.521(5) . ? C15 C16 1.523(6) . ? C9 O9 1.390(4) . ? C9 C10 1.520(5) . ? C10 C11 1.387(5) . ? C11 C12 1.376(7) . ? C12 C13 1.395(7) . ? C13 C1 1.377(6) . ? C1 C2 1.474(6) . ? Cl1 O3 1.415(4) . ? Cl1 O1 1.420(3) . ? Cl1 O4 1.430(4) . ? Cl1 O2 1.433(3) . ? Cl2 O5 1.282(8) . ? Cl2 O8 1.295(7) . ? Cl2 O6 1.326(7) . ? Cl2 O7 1.396(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N3 154.72(12) . . ? N1 Cu1 N2 79.15(13) . . ? N3 Cu1 N2 97.47(12) . . ? N1 Cu1 N4 79.19(12) . . ? N3 Cu1 N4 93.39(11) . . ? N2 Cu1 N4 150.06(12) . . ? N1 Cu1 N5 110.29(12) . . ? N3 Cu1 N5 94.97(12) . . ? N2 Cu1 N5 100.96(12) . . ? N4 Cu1 N5 105.80(11) . . ? C6 N3 C14 109.1(3) . . ? C6 N3 C5 107.6(3) . . ? C14 N3 C5 106.9(3) . . ? C6 N3 Cu1 107.2(2) . . ? C14 N3 Cu1 112.0(2) . . ? C5 N3 Cu1 114.0(2) . . ? C8 N4 C9 113.1(3) . . ? C8 N4 Cu1 105.02(18) . . ? C9 N4 Cu1 107.9(2) . . ? C2 N2 C3 121.6(3) . . ? C2 N2 Cu1 114.9(3) . . ? C3 N2 Cu1 123.5(2) . . ? C16 N5 Cu1 112.6(2) . . ? C10 N1 C1 121.1(3) . . ? C10 N1 Cu1 120.1(2) . . ? C1 N1 Cu1 117.5(3) . . ? N3 C6 C7 116.5(3) . . ? C8 C7 C6 116.8(3) . . ? N4 C8 C7 111.6(3) . . ? N3 C5 C4 116.8(3) . . ? C3 C4 C5 114.0(3) . . ? N2 C3 C4 110.0(3) . . ? N3 C14 C15 116.9(3) . . ? C14 C15 C16 115.8(3) . . ? N5 C16 C15 112.0(3) . . ? O9 C9 N4 112.2(3) . . ? O9 C9 C10 109.4(3) . . ? N4 C9 C10 107.0(3) . . ? N1 C10 C11 121.4(4) . . ? N1 C10 C9 112.9(3) . . ? C11 C10 C9 125.7(4) . . ? C12 C11 C10 118.3(4) . . ? C11 C12 C13 120.1(4) . . ? C1 C13 C12 118.5(4) . . ? N1 C1 C13 120.6(4) . . ? N1 C1 C2 111.3(3) . . ? C13 C1 C2 127.7(4) . . ? N2 C2 C1 116.8(3) . . ? O3 Cl1 O1 110.8(3) . . ? O3 Cl1 O4 110.8(3) . . ? O1 Cl1 O4 108.0(3) . . ? O3 Cl1 O2 109.2(2) . . ? O1 Cl1 O2 110.1(2) . . ? O4 Cl1 O2 107.9(2) . . ? O5 Cl2 O8 107.3(7) . . ? O5 Cl2 O6 100.5(10) . . ? O8 Cl2 O6 120.8(10) . . ? O5 Cl2 O7 114.4(8) . . ? O8 Cl2 O7 109.9(6) . . ? O6 Cl2 O7 103.9(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 N1 Cu1 N3 C6 -15.8(4) . . . . ? N2 Cu1 N3 C6 -96.2(2) . . . . ? N4 Cu1 N3 C6 55.9(2) . . . . ? N5 Cu1 N3 C6 162.1(2) . . . . ? N1 Cu1 N3 C14 -135.4(3) . . . . ? N2 Cu1 N3 C14 144.3(2) . . . . ? N4 Cu1 N3 C14 -63.7(2) . . . . ? N5 Cu1 N3 C14 42.5(2) . . . . ? N1 Cu1 N3 C5 103.2(3) . . . . ? N2 Cu1 N3 C5 22.8(2) . . . . ? N4 Cu1 N3 C5 174.8(2) . . . . ? N5 Cu1 N3 C5 -79.0(2) . . . . ? N1 Cu1 N4 C8 94.2(2) . . . . ? N3 Cu1 N4 C8 -61.4(2) . . . . ? N2 Cu1 N4 C8 49.9(3) . . . . ? N5 Cu1 N4 C8 -157.5(2) . . . . ? N1 Cu1 N4 C9 -26.6(2) . . . . ? N3 Cu1 N4 C9 177.7(2) . . . . ? N2 Cu1 N4 C9 -70.9(3) . . . . ? N5 Cu1 N4 C9 81.6(2) . . . . ? N1 Cu1 N2 C2 2.7(3) . . . . ? N3 Cu1 N2 C2 157.3(3) . . . . ? N4 Cu1 N2 C2 47.0(4) . . . . ? N5 Cu1 N2 C2 -106.1(3) . . . . ? N1 Cu1 N2 C3 -178.6(3) . . . . ? N3 Cu1 N2 C3 -24.0(3) . . . . ? N4 Cu1 N2 C3 -134.3(3) . . . . ? N5 Cu1 N2 C3 72.5(3) . . . . ? N1 Cu1 N5 C16 133.0(3) . . . . ? N3 Cu1 N5 C16 -46.1(3) . . . . ? N2 Cu1 N5 C16 -144.7(3) . . . . ? N4 Cu1 N5 C16 48.9(3) . . . . ? N3 Cu1 N1 C10 83.9(4) . . . . ? N2 Cu1 N1 C10 168.4(3) . . . . ? N4 Cu1 N1 C10 9.2(2) . . . . ? N5 Cu1 N1 C10 -93.8(3) . . . . ? N3 Cu1 N1 C1 -82.8(4) . . . . ? N2 Cu1 N1 C1 1.7(2) . . . . ? N4 Cu1 N1 C1 -157.5(3) . . . . ? N5 Cu1 N1 C1 99.5(2) . . . . ? C14 N3 C6 C7 61.0(4) . . . . ? C5 N3 C6 C7 176.6(3) . . . . ? Cu1 N3 C6 C7 -60.4(3) . . . . ? N3 C6 C7 C8 61.6(4) . . . . ? C9 N4 C8 C7 -173.9(3) . . . . ? Cu1 N4 C8 C7 68.7(3) . . . . ? C6 C7 C8 N4 -66.5(4) . . . . ? C6 N3 C5 C4 69.7(4) . . . . ? C14 N3 C5 C4 -173.2(3) . . . . ? Cu1 N3 C5 C4 -49.0(4) . . . . ? N3 C5 C4 C3 74.4(4) . . . . ? C2 N2 C3 C4 -136.3(4) . . . . ? Cu1 N2 C3 C4 45.1(4) . . . . ? C5 C4 C3 N2 -67.5(4) . . . . ? C6 N3 C14 C15 -175.9(3) . . . . ? C5 N3 C14 C15 68.0(4) . . . . ? Cu1 N3 C14 C15 -57.5(4) . . . . ? N3 C14 C15 C16 67.6(4) . . . . ? Cu1 N5 C16 C15 59.6(4) . . . . ? C14 C15 C16 N5 -68.0(4) . . . . ? C8 N4 C9 O9 42.2(4) . . . . ? Cu1 N4 C9 O9 157.9(3) . . . . ? C8 N4 C9 C10 -77.7(3) . . . . ? Cu1 N4 C9 C10 37.9(3) . . . . ? C1 N1 C10 C11 -1.1(5) . . . . ? Cu1 N1 C10 C11 -167.2(3) . . . . ? C1 N1 C10 C9 177.0(3) . . . . ? Cu1 N1 C10 C9 10.9(4) . . . . ? O9 C9 C10 N1 -154.5(3) . . . . ? N4 C9 C10 N1 -32.8(4) . . . . ? O9 C9 C10 C11 23.5(5) . . . . ? N4 C9 C10 C11 145.2(3) . . . . ? N1 C10 C11 C12 0.2(5) . . . . ? C9 C10 C11 C12 -177.6(3) . . . . ? C10 C11 C12 C13 0.2(6) . . . . ? C11 C12 C13 C1 0.2(6) . . . . ? C10 N1 C1 C13 1.5(5) . . . . ? Cu1 N1 C1 C13 168.0(3) . . . . ? C10 N1 C1 C2 -171.7(3) . . . . ? Cu1 N1 C1 C2 -5.2(4) . . . . ? C12 C13 C1 N1 -1.1(5) . . . . ? C12 C13 C1 C2 170.9(4) . . . . ? C3 N2 C2 C1 175.0(3) . . . . ? Cu1 N2 C2 C1 -6.3(4) . . . . ? N1 C1 C2 N2 7.5(5) . . . . ? C13 C1 C2 N2 -165.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.926 _refine_diff_density_max 1.461 _refine_diff_density_min -0.901 _refine_diff_density_rms 0.112 #---------------------------------------------------------------------- #==END data_CuL6 _database_code_CSD 215952 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H31 Cl2 Cu N5 O9' _chemical_formula_weight 595.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C/c _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 8.7216(16) _cell_length_b 15.582(3) _cell_length_c 18.389(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.446(4) _cell_angle_gamma 90.00 _cell_volume 2487.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3293 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.32 _exptl_crystal_description wedge _exptl_crystal_colour blue _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1236 _exptl_absorpt_coefficient_mu 1.150 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8937 _exptl_absorpt_correction_T_max 0.9554 _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer at 293 K. A suitable crystal was chosen and mounted on a glass fiber using epoxy. Data were measured using omega scans of 0.3\% per frame for 30 s , such that a hemisphere was collected. A total of 1650 frames were collected with a final resolution of 0.75 \%A. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 9524 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_av_sigmaI/netI 0.0660 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4353 _reflns_number_gt 3293 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.054, 1998)' _computing_data_reduction 'SAINT (BRUKER, V6.01, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 1998, V5.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.0577P)^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 0.012(14) _refine_ls_number_reflns 4353 _refine_ls_number_parameters 317 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 N5 N 0.7639(4) 0.0881(2) 0.2678(2) 0.0451(10) Uani 1 1 d . . . H5C H 0.7131 0.0386 0.2576 0.054 Uiso 1 1 calc R . . H5D H 0.7581 0.0998 0.3153 0.054 Uiso 1 1 calc R . . C7 C 1.1978(6) 0.1989(3) 0.1579(3) 0.0512(13) Uani 1 1 d . . . H7A H 1.2930 0.2122 0.1370 0.061 Uiso 1 1 calc R . . H7B H 1.1271 0.2459 0.1455 0.061 Uiso 1 1 calc R . . C6 C 1.1304(6) 0.1186(4) 0.1206(3) 0.0481(12) Uani 1 1 d . . . H6A H 1.1224 0.1281 0.0682 0.058 Uiso 1 1 calc R . . H6B H 1.2025 0.0719 0.1312 0.058 Uiso 1 1 calc R . . C8 C 1.2310(5) 0.1978(3) 0.2384(3) 0.0461(12) Uani 1 1 d . . . H8A H 1.2867 0.2496 0.2539 0.055 Uiso 1 1 calc R . . H8B H 1.2963 0.1491 0.2524 0.055 Uiso 1 1 calc R . . C14 C 0.8597(6) 0.1587(4) 0.1205(3) 0.0521(14) Uani 1 1 d . . . H14A H 0.8511 0.1651 0.0678 0.063 Uiso 1 1 calc R . . H14B H 0.8989 0.2125 0.1414 0.063 Uiso 1 1 calc R . . C16 C 0.6865(5) 0.1568(4) 0.2240(3) 0.0532(14) Uani 1 1 d . . . H16A H 0.7313 0.2116 0.2394 0.064 Uiso 1 1 calc R . . H16B H 0.5784 0.1580 0.2324 0.064 Uiso 1 1 calc R . . C15 C 0.7007(6) 0.1445(4) 0.1439(3) 0.0615(16) Uani 1 1 d . . . H15A H 0.6301 0.1835 0.1167 0.074 Uiso 1 1 calc R . . H15B H 0.6686 0.0865 0.1306 0.074 Uiso 1 1 calc R . . C5 C 0.9304(7) 0.0111(4) 0.0976(3) 0.0575(15) Uani 1 1 d . . . H5A H 0.8228 -0.0006 0.1029 0.069 Uiso 1 1 calc R . . H5B H 0.9380 0.0243 0.0465 0.069 Uiso 1 1 calc R . . C4 C 1.0185(6) -0.0694(3) 0.1149(3) 0.0507(13) Uani 1 1 d . . . H4A H 1.1277 -0.0564 0.1193 0.061 Uiso 1 1 calc R . . H4B H 0.9982 -0.1094 0.0747 0.061 Uiso 1 1 calc R . . C3 C 0.9787(6) -0.1120(3) 0.1845(3) 0.0481(13) Uani 1 1 d . . . H3A H 0.8683 -0.1210 0.1823 0.058 Uiso 1 1 calc R . . H3B H 1.0287 -0.1676 0.1895 0.058 Uiso 1 1 calc R . . C2 C 1.0973(6) -0.0917(4) 0.3044(3) 0.0451(13) Uani 1 1 d . . . H2 H 1.1114 -0.1506 0.3098 0.054 Uiso 1 1 calc R . . O8 O 0.4248(9) 0.9383(7) 0.1317(4) 0.178(4) Uani 1 1 d . . . Cl3 Cl 0.45829(13) 0.92273(9) 0.20432(8) 0.0520(3) Uani 1 1 d . . . O2 O 0.3798(5) 0.8490(3) 0.2253(3) 0.0952(17) Uani 1 1 d . . . O3 O 0.6172(4) 0.9091(3) 0.2198(3) 0.0744(13) Uani 1 1 d . . . O6 O 0.4087(6) 0.9927(3) 0.2428(4) 0.119(2) Uani 1 1 d . . . C9 C 1.1103(6) 0.1988(3) 0.3559(3) 0.0434(12) Uani 1 1 d . . . H9 H 1.0103 0.2101 0.3743 0.052 Uiso 1 1 calc R . . C10 C 1.1700(6) 0.1152(4) 0.3862(3) 0.0456(12) Uani 1 1 d . . . O5 O 1.2124(4) 0.2636(2) 0.3809(2) 0.0616(10) Uani 1 1 d . . . C17 C 1.1436(9) 0.3405(4) 0.4033(4) 0.078(2) Uani 1 1 d . . . H17A H 1.1070 0.3327 0.4510 0.094 Uiso 1 1 calc R . . H17B H 1.0565 0.3555 0.3689 0.094 Uiso 1 1 calc R . . C11 C 1.2686(7) 0.1010(5) 0.4472(3) 0.0630(16) Uani 1 1 d . . . H11 H 1.3084 0.1468 0.4754 0.076 Uiso 1 1 calc R . . C12 C 1.3083(8) 0.0179(5) 0.4664(3) 0.0702(18) Uani 1 1 d . . . H12 H 1.3737 0.0074 0.5083 0.084 Uiso 1 1 calc R . . C13 C 1.2513(7) -0.0504(4) 0.4234(3) 0.0610(15) Uani 1 1 d . . . H13 H 1.2775 -0.1067 0.4358 0.073 Uiso 1 1 calc R . . C1 C 1.1539(5) -0.0318(4) 0.3613(3) 0.0450(13) Uani 1 1 d . . . C18 C 1.2592(11) 0.4089(5) 0.4062(5) 0.102(3) Uani 1 1 d . . . H18A H 1.3455 0.3933 0.4399 0.153 Uiso 1 1 calc R . . H18B H 1.2148 0.4613 0.4221 0.153 Uiso 1 1 calc R . . H18C H 1.2931 0.4171 0.3585 0.153 Uiso 1 1 calc R . . O4 O 0.3502(6) 0.2564(4) 1.0004(3) 0.0942(15) Uani 1 1 d . . . O10 O 0.1090(10) 0.2963(10) 0.9953(5) 0.301(9) Uani 1 1 d . . . Cl1 Cl 0.2293(2) 0.30377(11) 0.96059(8) 0.0724(5) Uani 1 1 d . . . O7 O 0.2861(14) 0.3843(5) 0.9506(5) 0.208(5) Uani 1 1 d . . . O9 O 0.2079(10) 0.2733(5) 0.8900(3) 0.150(3) Uani 1 1 d . . . Cu1 Cu 0.99946(3) 0.07022(3) 0.24999(2) 0.03644(15) Uani 1 1 d . . . N1 N 1.1131(5) 0.0500(3) 0.3450(2) 0.0420(10) Uani 1 1 d . . . N4 N 1.0880(4) 0.1925(3) 0.2758(2) 0.0402(9) Uani 1 1 d . . . H4C H 1.0200 0.2332 0.2577 0.048 Uiso 1 1 calc R . . N2 N 1.0276(4) -0.0597(2) 0.2470(3) 0.0409(9) Uani 1 1 d . . . N3 N 0.9750(5) 0.0903(3) 0.1411(2) 0.0438(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N5 0.038(2) 0.035(2) 0.064(3) -0.0064(19) 0.0121(19) -0.0034(17) C7 0.052(3) 0.038(3) 0.066(4) 0.014(3) 0.019(2) -0.007(2) C6 0.057(3) 0.047(3) 0.043(3) 0.004(2) 0.015(2) -0.003(3) C8 0.043(3) 0.042(3) 0.055(3) 0.002(2) 0.011(2) -0.010(2) C14 0.059(3) 0.049(4) 0.046(3) 0.004(3) -0.008(3) 0.001(3) C16 0.038(2) 0.038(3) 0.084(4) 0.002(3) 0.009(3) 0.009(2) C15 0.054(3) 0.063(4) 0.066(4) -0.009(3) -0.007(3) 0.008(3) C5 0.068(3) 0.054(4) 0.049(3) -0.013(3) -0.002(3) -0.005(3) C4 0.052(3) 0.043(3) 0.057(3) -0.013(3) 0.004(2) 0.001(2) C3 0.047(3) 0.029(3) 0.069(4) -0.007(3) 0.007(3) -0.001(2) C2 0.047(3) 0.035(3) 0.056(4) 0.004(2) 0.017(3) 0.002(2) O8 0.127(6) 0.323(14) 0.081(5) 0.062(6) -0.004(4) 0.039(6) Cl3 0.0413(7) 0.0479(8) 0.0665(9) 0.0072(7) 0.0037(6) 0.0032(6) O2 0.062(2) 0.044(3) 0.183(6) 0.009(3) 0.032(3) -0.003(2) O3 0.0406(19) 0.065(3) 0.117(4) -0.008(2) 0.005(2) 0.0013(18) O6 0.080(3) 0.056(3) 0.227(8) -0.044(4) 0.048(4) 0.000(3) C9 0.047(3) 0.033(3) 0.050(3) -0.011(2) 0.001(2) -0.005(2) C10 0.048(3) 0.047(3) 0.043(3) -0.003(3) 0.005(2) -0.004(2) O5 0.061(2) 0.042(2) 0.080(3) -0.016(2) -0.0027(19) -0.0084(18) C17 0.103(5) 0.048(4) 0.084(5) -0.023(3) 0.017(4) -0.015(4) C11 0.066(4) 0.072(4) 0.050(4) -0.005(3) -0.003(3) 0.003(3) C12 0.078(4) 0.083(5) 0.046(4) 0.003(3) -0.010(3) 0.003(4) C13 0.072(4) 0.060(4) 0.051(3) 0.016(3) 0.007(3) 0.011(3) C1 0.049(3) 0.044(3) 0.043(3) 0.015(2) 0.012(2) 0.007(2) C18 0.141(8) 0.073(5) 0.088(6) -0.001(4) -0.012(5) -0.029(5) O4 0.089(3) 0.085(4) 0.107(4) 0.013(3) 0.004(3) 0.016(3) O10 0.143(6) 0.60(3) 0.174(8) 0.221(12) 0.102(6) 0.192(11) Cl1 0.0987(11) 0.0633(11) 0.0574(11) 0.0005(7) 0.0185(9) 0.0024(10) O7 0.372(14) 0.064(4) 0.166(8) 0.017(4) -0.086(8) -0.036(6) O9 0.218(8) 0.135(6) 0.088(4) -0.014(4) -0.030(4) -0.039(6) Cu1 0.0361(3) 0.0320(3) 0.0414(3) -0.0003(3) 0.0044(2) 0.0004(3) N1 0.043(2) 0.042(3) 0.041(2) 0.010(2) 0.0062(18) 0.0036(19) N4 0.038(2) 0.040(2) 0.043(2) -0.0014(18) 0.0048(16) 0.0000(17) N2 0.040(2) 0.033(2) 0.051(2) -0.002(2) 0.012(2) 0.0021(18) N3 0.049(2) 0.043(3) 0.040(2) -0.0051(18) 0.0035(18) 0.0017(19) _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 N5 C16 1.466(7) . ? N5 Cu1 2.129(4) . ? N5 H5C 0.9000 . ? N5 H5D 0.9000 . ? C7 C8 1.480(7) . ? C7 C6 1.519(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C6 N3 1.507(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 N4 1.484(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C14 N3 1.489(7) . ? C14 C15 1.507(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C16 C15 1.502(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C5 C4 1.490(8) . ? C5 N3 1.502(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C4 C3 1.512(8) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C3 N2 1.438(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C2 N2 1.270(7) . ? C2 C1 1.453(8) . ? C2 H2 0.9300 . ? O8 Cl3 1.362(7) . ? Cl3 O6 1.392(5) . ? Cl3 O3 1.405(4) . ? Cl3 O2 1.409(5) . ? C9 O5 1.394(6) . ? C9 N4 1.471(6) . ? C9 C10 1.492(7) . ? C9 H9 0.9800 . ? C10 N1 1.334(7) . ? C10 C11 1.365(8) . ? O5 C17 1.418(8) . ? C17 C18 1.466(10) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C11 C12 1.377(10) . ? C11 H11 0.9300 . ? C12 C13 1.389(9) . ? C12 H12 0.9300 . ? C13 C1 1.387(8) . ? C13 H13 0.9300 . ? C1 N1 1.349(7) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O4 Cl1 1.429(5) . ? O10 Cl1 1.284(7) . ? Cl1 O7 1.368(8) . ? Cl1 O9 1.379(6) . ? Cu1 N1 1.951(4) . ? Cu1 N3 2.018(4) . ? Cu1 N2 2.041(4) . ? Cu1 N4 2.093(4) . ? N4 H4C 0.9100 . ? 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 C16 N5 Cu1 114.4(3) . . ? C16 N5 H5C 108.7 . . ? Cu1 N5 H5C 108.7 . . ? C16 N5 H5D 108.7 . . ? Cu1 N5 H5D 108.7 . . ? H5C N5 H5D 107.6 . . ? C8 C7 C6 118.3(4) . . ? C8 C7 H7A 107.7 . . ? C6 C7 H7A 107.7 . . ? C8 C7 H7B 107.7 . . ? C6 C7 H7B 107.7 . . ? H7A C7 H7B 107.1 . . ? N3 C6 C7 116.5(4) . . ? N3 C6 H6A 108.2 . . ? C7 C6 H6A 108.2 . . ? N3 C6 H6B 108.2 . . ? C7 C6 H6B 108.2 . . ? H6A C6 H6B 107.3 . . ? C7 C8 N4 111.8(4) . . ? C7 C8 H8A 109.3 . . ? N4 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? N4 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? N3 C14 C15 116.0(5) . . ? N3 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? N3 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? N5 C16 C15 111.6(4) . . ? N5 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? N5 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C16 C15 C14 115.2(5) . . ? C16 C15 H15A 108.5 . . ? C14 C15 H15A 108.5 . . ? C16 C15 H15B 108.5 . . ? C14 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C4 C5 N3 118.4(5) . . ? C4 C5 H5A 107.7 . . ? N3 C5 H5A 107.7 . . ? C4 C5 H5B 107.7 . . ? N3 C5 H5B 107.7 . . ? H5A C5 H5B 107.1 . . ? C5 C4 C3 113.3(5) . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? N2 C3 C4 110.7(4) . . ? N2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N2 C2 C1 116.7(5) . . ? N2 C2 H2 121.6 . . ? C1 C2 H2 121.6 . . ? O8 Cl3 O6 108.1(5) . . ? O8 Cl3 O3 110.0(4) . . ? O6 Cl3 O3 111.3(3) . . ? O8 Cl3 O2 110.4(5) . . ? O6 Cl3 O2 108.5(3) . . ? O3 Cl3 O2 108.5(3) . . ? O5 C9 N4 113.4(4) . . ? O5 C9 C10 108.7(4) . . ? N4 C9 C10 108.8(4) . . ? O5 C9 H9 108.6 . . ? N4 C9 H9 108.6 . . ? C10 C9 H9 108.6 . . ? N1 C10 C11 121.0(6) . . ? N1 C10 C9 110.8(5) . . ? C11 C10 C9 128.2(5) . . ? C9 O5 C17 115.6(4) . . ? O5 C17 C18 108.5(6) . . ? O5 C17 H17A 110.0 . . ? C18 C17 H17A 110.0 . . ? O5 C17 H17B 110.0 . . ? C18 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? C10 C11 C12 119.1(6) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C11 C12 C13 120.4(6) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C1 C13 C12 117.8(6) . . ? C1 C13 H13 121.1 . . ? C12 C13 H13 121.1 . . ? N1 C1 C13 120.5(5) . . ? N1 C1 C2 112.5(5) . . ? C13 C1 C2 126.7(5) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O10 Cl1 O7 118.2(9) . . ? O10 Cl1 O9 113.1(7) . . ? O7 Cl1 O9 102.0(5) . . ? O10 Cl1 O4 107.3(4) . . ? O7 Cl1 O4 106.5(5) . . ? O9 Cl1 O4 109.4(4) . . ? N1 Cu1 N3 155.60(16) . . ? N1 Cu1 N2 79.2(2) . . ? N3 Cu1 N2 97.37(19) . . ? N1 Cu1 N4 78.38(17) . . ? N3 Cu1 N4 94.94(16) . . ? N2 Cu1 N4 150.04(16) . . ? N1 Cu1 N5 107.42(17) . . ? N3 Cu1 N5 96.85(17) . . ? N2 Cu1 N5 104.72(15) . . ? N4 Cu1 N5 100.78(15) . . ? C10 N1 C1 121.1(5) . . ? C10 N1 Cu1 121.0(4) . . ? C1 N1 Cu1 116.9(4) . . ? C9 N4 C8 115.1(4) . . ? C9 N4 Cu1 107.4(3) . . ? C8 N4 Cu1 104.7(3) . . ? C9 N4 H4C 109.8 . . ? C8 N4 H4C 109.8 . . ? Cu1 N4 H4C 109.8 . . ? C2 N2 C3 121.6(4) . . ? C2 N2 Cu1 114.6(4) . . ? C3 N2 Cu1 123.8(4) . . ? C14 N3 C5 108.6(4) . . ? C14 N3 C6 109.1(4) . . ? C5 N3 C6 107.5(4) . . ? C14 N3 Cu1 111.6(3) . . ? C5 N3 Cu1 113.5(3) . . ? C6 N3 Cu1 106.3(3) . . ? 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 C8 C7 C6 N3 62.1(6) . . . . ? C6 C7 C8 N4 -67.1(6) . . . . ? Cu1 N5 C16 C15 54.7(5) . . . . ? N5 C16 C15 C14 -70.5(7) . . . . ? N3 C14 C15 C16 73.8(7) . . . . ? N3 C5 C4 C3 74.9(6) . . . . ? C5 C4 C3 N2 -66.9(6) . . . . ? O5 C9 C10 N1 -157.0(4) . . . . ? N4 C9 C10 N1 -33.1(6) . . . . ? O5 C9 C10 C11 23.3(7) . . . . ? N4 C9 C10 C11 147.3(5) . . . . ? N4 C9 O5 C17 100.9(6) . . . . ? C10 C9 O5 C17 -137.9(5) . . . . ? C9 O5 C17 C18 -163.0(6) . . . . ? N1 C10 C11 C12 -0.5(8) . . . . ? C9 C10 C11 C12 179.2(5) . . . . ? C10 C11 C12 C13 1.3(9) . . . . ? C11 C12 C13 C1 -0.1(9) . . . . ? C12 C13 C1 N1 -1.9(8) . . . . ? C12 C13 C1 C2 171.7(5) . . . . ? N2 C2 C1 N1 4.1(6) . . . . ? N2 C2 C1 C13 -170.0(5) . . . . ? C16 N5 Cu1 N1 138.9(4) . . . . ? C16 N5 Cu1 N3 -38.6(4) . . . . ? C16 N5 Cu1 N2 -138.1(4) . . . . ? C16 N5 Cu1 N4 57.8(4) . . . . ? C11 C10 N1 C1 -1.6(7) . . . . ? C9 C10 N1 C1 178.7(4) . . . . ? C11 C10 N1 Cu1 -170.1(4) . . . . ? C9 C10 N1 Cu1 10.2(6) . . . . ? C13 C1 N1 C10 2.8(7) . . . . ? C2 C1 N1 C10 -171.7(4) . . . . ? C13 C1 N1 Cu1 171.8(4) . . . . ? C2 C1 N1 Cu1 -2.7(5) . . . . ? N3 Cu1 N1 C10 85.9(6) . . . . ? N2 Cu1 N1 C10 169.8(4) . . . . ? N4 Cu1 N1 C10 9.8(4) . . . . ? N5 Cu1 N1 C10 -88.0(4) . . . . ? N3 Cu1 N1 C1 -83.1(5) . . . . ? N2 Cu1 N1 C1 0.8(3) . . . . ? N4 Cu1 N1 C1 -159.2(4) . . . . ? N5 Cu1 N1 C1 103.0(3) . . . . ? O5 C9 N4 C8 44.2(6) . . . . ? C10 C9 N4 C8 -76.9(5) . . . . ? O5 C9 N4 Cu1 160.4(3) . . . . ? C10 C9 N4 Cu1 39.3(4) . . . . ? C7 C8 N4 C9 -174.8(4) . . . . ? C7 C8 N4 Cu1 67.5(4) . . . . ? N1 Cu1 N4 C9 -26.9(3) . . . . ? N3 Cu1 N4 C9 176.8(3) . . . . ? N2 Cu1 N4 C9 -69.1(5) . . . . ? N5 Cu1 N4 C9 78.9(3) . . . . ? N1 Cu1 N4 C8 95.9(3) . . . . ? N3 Cu1 N4 C8 -60.3(3) . . . . ? N2 Cu1 N4 C8 53.7(5) . . . . ? N5 Cu1 N4 C8 -158.3(3) . . . . ? C1 C2 N2 C3 174.4(4) . . . . ? C1 C2 N2 Cu1 -3.4(5) . . . . ? C4 C3 N2 C2 -134.8(5) . . . . ? C4 C3 N2 Cu1 42.8(5) . . . . ? N1 Cu1 N2 C2 1.5(3) . . . . ? N3 Cu1 N2 C2 157.0(3) . . . . ? N4 Cu1 N2 C2 43.6(5) . . . . ? N5 Cu1 N2 C2 -103.9(3) . . . . ? N1 Cu1 N2 C3 -176.3(4) . . . . ? N3 Cu1 N2 C3 -20.7(3) . . . . ? N4 Cu1 N2 C3 -134.2(4) . . . . ? N5 Cu1 N2 C3 78.4(4) . . . . ? C15 C14 N3 C5 68.8(6) . . . . ? C15 C14 N3 C6 -174.3(5) . . . . ? C15 C14 N3 Cu1 -57.1(6) . . . . ? C4 C5 N3 C14 -173.0(5) . . . . ? C4 C5 N3 C6 69.0(6) . . . . ? C4 C5 N3 Cu1 -48.3(6) . . . . ? C7 C6 N3 C14 61.9(6) . . . . ? C7 C6 N3 C5 179.5(5) . . . . ? C7 C6 N3 Cu1 -58.7(5) . . . . ? N1 Cu1 N3 C14 -137.0(4) . . . . ? N2 Cu1 N3 C14 143.0(3) . . . . ? N4 Cu1 N3 C14 -64.4(4) . . . . ? N5 Cu1 N3 C14 37.1(4) . . . . ? N1 Cu1 N3 C5 99.9(5) . . . . ? N2 Cu1 N3 C5 19.9(4) . . . . ? N4 Cu1 N3 C5 172.5(3) . . . . ? N5 Cu1 N3 C5 -86.0(3) . . . . ? N1 Cu1 N3 C6 -18.1(6) . . . . ? N2 Cu1 N3 C6 -98.1(3) . . . . ? N4 Cu1 N3 C6 54.5(3) . . . . ? N5 Cu1 N3 C6 156.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.395 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.063 #==END data_NiL8 _database_code_CSD 215953 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H33 Cl2 N5 Ni O10' _chemical_formula_weight 633.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P na21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 16.434(9) _cell_length_b 10.2465(9) _cell_length_c 16.4336(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2767.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2686 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 21.93 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 0.954 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer at 293 K. A suitable crystal was chosen and mounted on a glass fiber using epoxy. Data were measured using omega scans of 0.3\% per frame for 30 s , such that a hemisphere was collected. A total of 1650 frames were collected with a final resolution of 0.75 \%A. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19631 _diffrn_reflns_av_R_equivalents 0.0805 _diffrn_reflns_av_sigmaI/netI 0.1211 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 28.33 _reflns_number_total 5640 _reflns_number_gt 2608 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0573P)^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 0.015(19) _refine_ls_number_reflns 5640 _refine_ls_number_parameters 351 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1255 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 0.820 _refine_ls_restrained_S_all 0.820 _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 O9 O 0.2188(2) 0.0062(4) 0.8212(2) 0.0704(11) Uani 1 1 d . . . H9C H 0.1785 -0.0145 0.7836 0.084 Uiso 1 1 calc R . . Ni1 Ni 0.34127(3) 0.06615(6) 0.78532(5) 0.0496(2) Uani 1 1 d . . . C11 C 0.3607(3) -0.2312(6) 0.7952(4) 0.0565(15) Uani 1 1 d . . . N1 N 0.3275(3) 0.1271(5) 0.9023(3) 0.0628(13) Uani 1 1 d . . . N2 N 0.4566(3) 0.1435(5) 0.8070(3) 0.0620(13) Uani 1 1 d . . . H2C H 0.4865 0.0764 0.8276 0.074 Uiso 1 1 calc R . . C9 C 0.3744(4) -0.1330(7) 0.6563(3) 0.074(2) Uani 1 1 d . . . H9A H 0.4316 -0.1455 0.6687 0.089 Uiso 1 1 calc R . . H9B H 0.3657 -0.1606 0.6005 0.089 Uiso 1 1 calc R . . C2 C 0.4499(4) 0.2387(6) 0.8735(4) 0.078(2) Uani 1 1 d . . . H2A H 0.5025 0.2487 0.8996 0.094 Uiso 1 1 calc R . . H2B H 0.4341 0.3228 0.8515 0.094 Uiso 1 1 calc R . . C1 C 0.3896(4) 0.1961(6) 0.9337(5) 0.0725(18) Uani 1 1 d . . . N3 N 0.3551(3) 0.0081(5) 0.6628(3) 0.0535(12) Uani 1 1 d . . . N5 N 0.3802(3) -0.1212(5) 0.8317(3) 0.0521(12) Uani 1 1 d . . . C15 C 0.4190(4) -0.1308(6) 0.9042(3) 0.0627(17) Uani 1 1 d . . . H15 H 0.4354 -0.0543 0.9298 0.075 Uiso 1 1 calc R . . N4 N 0.2909(3) 0.2428(5) 0.7431(3) 0.0718(14) Uani 1 1 d . . . H4A H 0.2740 0.2892 0.7864 0.086 Uiso 1 1 calc R . . H4B H 0.3306 0.2890 0.7186 0.086 Uiso 1 1 calc R . . C10 C 0.3245(4) -0.2188(6) 0.7119(3) 0.0638(17) Uani 1 1 d . . . H10A H 0.2701 -0.1829 0.7165 0.077 Uiso 1 1 calc R . . H10B H 0.3199 -0.3050 0.6878 0.077 Uiso 1 1 calc R . . Cl1 Cl 0.65857(15) 0.9824(2) 0.87115(13) 0.1019(7) Uani 1 1 d . . . O4 O 0.5970(4) 1.0504(7) 0.9157(4) 0.164(3) Uani 1 1 d . . . C5 C 0.4226(4) 0.0802(7) 0.6210(4) 0.083(2) Uani 1 1 d . . . H5A H 0.4030 0.1667 0.6071 0.099 Uiso 1 1 calc R . . H5B H 0.4348 0.0354 0.5704 0.099 Uiso 1 1 calc R . . Cl2 Cl 0.46320(12) 0.50394(18) 0.60623(10) 0.0724(5) Uani 1 1 d . . . C14 C 0.4351(4) -0.2458(7) 0.9414(4) 0.080(2) Uani 1 1 d . . . H14 H 0.4597 -0.2472 0.9924 0.096 Uiso 1 1 calc R . . C12 C 0.3756(4) -0.3507(6) 0.8300(4) 0.0772(19) Uani 1 1 d . . . H12 H 0.3587 -0.4261 0.8033 0.093 Uiso 1 1 calc R . . C7 C 0.2459(4) 0.1646(7) 0.6084(4) 0.078(2) Uani 1 1 d . . . H7A H 0.1985 0.1618 0.5732 0.094 Uiso 1 1 calc R . . H7B H 0.2868 0.2174 0.5815 0.094 Uiso 1 1 calc R . . O6 O 0.3966(4) 0.4458(6) 0.6385(4) 0.152(3) Uani 1 1 d . . . C13 C 0.4147(5) -0.3608(7) 0.9029(4) 0.095(3) Uani 1 1 d . . . H13 H 0.4270 -0.4416 0.9256 0.114 Uiso 1 1 calc R . . C4 C 0.5030(3) 0.0952(7) 0.6696(4) 0.080(2) Uani 1 1 d . . . H4C H 0.5169 0.0107 0.6923 0.096 Uiso 1 1 calc R . . H4D H 0.5458 0.1186 0.6316 0.096 Uiso 1 1 calc R . . O3 O 0.6813(4) 0.8675(6) 0.9124(4) 0.139(2) Uani 1 1 d . . . O8 O 0.5332(4) 0.4299(5) 0.6034(4) 0.1241(19) Uani 1 1 d . . . O7 O 0.4458(4) 0.5723(7) 0.5361(4) 0.163(3) Uani 1 1 d . . . C3 C 0.5032(4) 0.1920(7) 0.7365(4) 0.090(2) Uani 1 1 d . . . H3A H 0.5588 0.2096 0.7530 0.109 Uiso 1 1 calc R . . H3B H 0.4794 0.2731 0.7175 0.109 Uiso 1 1 calc R . . O5 O 0.4842(5) 0.6031(8) 0.6624(5) 0.181(3) Uani 1 1 d . . . O1 O 0.7238(6) 1.0627(9) 0.8747(6) 0.227(5) Uani 1 1 d . . . C6 C 0.2776(4) 0.0320(6) 0.6168(3) 0.0663(19) Uani 1 1 d . . . H6A H 0.2851 -0.0025 0.5624 0.080 Uiso 1 1 calc R . . H6B H 0.2355 -0.0201 0.6424 0.080 Uiso 1 1 calc R . . C8 C 0.2224(4) 0.2308(6) 0.6859(4) 0.0773(19) Uani 1 1 d . . . H8A H 0.2016 0.3171 0.6736 0.093 Uiso 1 1 calc R . . H8B H 0.1790 0.1817 0.7117 0.093 Uiso 1 1 calc R . . C19 C 0.3321(6) 0.1660(9) 1.0653(5) 0.120(3) Uani 1 1 d . . . H19 H 0.3349 0.1766 1.1215 0.144 Uiso 1 1 calc R . . C16 C 0.2054(5) 0.0013(9) 0.9078(4) 0.110(3) Uani 1 1 d . . . H16A H 0.2085 -0.0882 0.9267 0.132 Uiso 1 1 calc R . . H16B H 0.1518 0.0351 0.9207 0.132 Uiso 1 1 calc R . . C20 C 0.3919(5) 0.2196(9) 1.0178(5) 0.104(3) Uani 1 1 d . . . H20 H 0.4329 0.2703 1.0407 0.125 Uiso 1 1 calc R . . C17 C 0.2693(5) 0.0822(7) 0.9488(4) 0.076(2) Uani 1 1 d . . . C18 C 0.2691(5) 0.0980(9) 1.0334(4) 0.103(3) Uani 1 1 d . . . H18 H 0.2280 0.0637 1.0659 0.123 Uiso 1 1 calc R . . O2 O 0.6344(7) 0.9557(9) 0.8002(5) 0.299(7) Uani 1 1 d . . . O1S O 0.1159(4) 0.8320(7) 0.7580(4) 0.122(2) Uani 1 1 d . . . H2S H 0.089(3) 0.863(5) 0.804(3) 0.040(16) Uiso 1 1 d . . . H1S H 0.062(5) 0.853(9) 0.753(6) 0.15(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O9 0.053(2) 0.105(3) 0.054(2) -0.015(2) 0.0062(17) -0.017(2) Ni1 0.0410(3) 0.0468(4) 0.0610(4) -0.0032(5) 0.0030(4) -0.0002(4) C11 0.070(4) 0.051(4) 0.048(3) -0.005(4) 0.011(3) -0.005(3) N1 0.035(3) 0.067(3) 0.086(3) -0.023(3) -0.003(3) 0.000(3) N2 0.057(3) 0.054(3) 0.075(4) 0.012(3) 0.004(2) -0.003(2) C9 0.093(6) 0.088(6) 0.042(3) -0.014(3) 0.011(3) 0.004(4) C2 0.076(5) 0.046(4) 0.113(5) -0.002(4) -0.015(4) -0.011(3) C1 0.065(5) 0.047(4) 0.105(5) -0.020(4) -0.008(4) 0.008(4) N3 0.050(3) 0.057(3) 0.053(2) 0.007(3) 0.006(2) 0.006(3) N5 0.056(3) 0.051(3) 0.049(3) -0.003(2) -0.001(2) -0.009(2) C15 0.084(5) 0.048(4) 0.056(4) -0.006(3) 0.001(3) -0.013(4) N4 0.052(3) 0.068(4) 0.096(3) -0.008(3) 0.003(3) 0.007(3) C10 0.080(5) 0.058(4) 0.054(3) -0.004(3) 0.001(3) 0.003(3) Cl1 0.0833(14) 0.1195(18) 0.1029(15) 0.0352(14) -0.0087(13) 0.0139(15) O4 0.143(6) 0.192(7) 0.159(6) 0.014(5) -0.025(5) 0.064(5) C5 0.068(5) 0.101(6) 0.079(4) 0.027(4) 0.023(4) 0.010(4) Cl2 0.0851(13) 0.0589(11) 0.0732(10) 0.0057(9) 0.0151(9) 0.0099(11) C14 0.131(6) 0.061(5) 0.047(3) 0.007(4) -0.013(4) -0.002(4) C12 0.127(6) 0.044(4) 0.061(4) -0.007(3) 0.006(4) -0.012(4) C7 0.062(4) 0.081(5) 0.092(5) 0.005(4) -0.009(4) 0.018(4) O6 0.091(4) 0.103(5) 0.263(8) 0.077(5) 0.030(5) -0.010(3) C13 0.174(8) 0.052(5) 0.059(4) 0.012(4) -0.007(4) 0.003(5) C4 0.041(4) 0.120(6) 0.079(4) 0.044(4) 0.010(3) 0.007(4) O3 0.173(6) 0.122(5) 0.121(4) 0.058(4) -0.014(4) 0.025(4) O8 0.115(5) 0.112(4) 0.145(5) 0.006(4) 0.034(4) 0.034(4) O7 0.138(6) 0.219(7) 0.131(5) 0.094(5) -0.043(4) -0.042(5) C3 0.065(5) 0.103(6) 0.104(5) 0.026(5) 0.003(4) -0.019(4) O5 0.153(7) 0.219(8) 0.170(5) -0.086(6) -0.021(5) 0.041(6) O1 0.174(8) 0.210(9) 0.297(12) 0.076(8) 0.043(8) -0.067(7) C6 0.067(5) 0.076(5) 0.056(3) -0.009(3) -0.004(3) 0.008(4) C8 0.050(4) 0.069(5) 0.114(5) 0.014(4) -0.001(4) 0.011(3) C19 0.112(7) 0.153(9) 0.094(6) -0.052(6) 0.009(6) -0.008(7) C16 0.082(5) 0.184(8) 0.065(4) -0.036(5) 0.022(4) -0.050(6) C20 0.086(6) 0.131(8) 0.095(5) -0.060(5) -0.010(5) -0.018(5) C17 0.060(5) 0.094(6) 0.075(5) -0.037(4) 0.002(4) -0.005(4) C18 0.082(6) 0.162(8) 0.065(4) -0.055(5) 0.015(4) -0.018(5) O2 0.536(18) 0.255(9) 0.107(6) -0.076(6) -0.151(8) 0.233(11) O1S 0.088(5) 0.154(6) 0.125(5) -0.030(4) -0.011(4) -0.034(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O9 C16 1.441(7) . ? O9 Ni1 2.185(4) . ? O9 H9C 0.9300 . ? Ni1 N1 2.033(5) . ? Ni1 N2 2.085(4) . ? Ni1 N4 2.108(5) . ? Ni1 N3 2.112(4) . ? Ni1 N5 2.162(5) . ? C11 N5 1.316(6) . ? C11 C12 1.373(8) . ? C11 C10 1.499(8) . ? N1 C17 1.308(8) . ? N1 C1 1.345(7) . ? N2 C2 1.468(7) . ? N2 C3 1.474(7) . ? N2 H2C 0.9100 . ? C9 N3 1.484(8) . ? C9 C10 1.510(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C2 C1 1.468(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C1 C20 1.403(10) . ? N3 C5 1.500(7) . ? N3 C6 1.500(7) . ? N5 C15 1.355(7) . ? C15 C14 1.354(8) . ? C15 H15 0.9300 . ? N4 C8 1.471(7) . ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? Cl1 O2 1.262(7) . ? Cl1 O1 1.353(8) . ? Cl1 O3 1.409(6) . ? Cl1 O4 1.430(7) . ? C5 C4 1.552(9) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? Cl2 O6 1.355(6) . ? Cl2 O7 1.379(5) . ? Cl2 O8 1.378(5) . ? Cl2 O5 1.416(7) . ? C14 C13 1.380(8) . ? C14 H14 0.9300 . ? C12 C13 1.363(9) . ? C12 H12 0.9300 . ? C7 C6 1.462(8) . ? C7 C8 1.494(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C13 H13 0.9300 . ? C4 C3 1.482(9) . ? C4 H4C 0.9700 . ? C4 H4D 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C19 C18 1.354(10) . ? C19 C20 1.370(11) . ? C19 H19 0.9300 . ? C16 C17 1.497(9) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C20 H20 0.9300 . ? C17 C18 1.400(9) . ? C18 H18 0.9300 . ? O1S H2S 0.93(5) . ? O1S H1S 0.92(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 O9 Ni1 114.6(4) . . ? C16 O9 H9C 122.7 . . ? Ni1 O9 H9C 122.7 . . ? N1 Ni1 N2 79.80(18) . . ? N1 Ni1 N4 90.2(2) . . ? N2 Ni1 N4 94.97(19) . . ? N1 Ni1 N3 178.5(2) . . ? N2 Ni1 N3 99.93(17) . . ? N4 Ni1 N3 88.28(19) . . ? N1 Ni1 N5 88.41(19) . . ? N2 Ni1 N5 90.48(18) . . ? N4 Ni1 N5 174.06(18) . . ? N3 Ni1 N5 93.11(18) . . ? N1 Ni1 O9 74.27(17) . . ? N2 Ni1 O9 153.88(15) . . ? N4 Ni1 O9 88.21(17) . . ? N3 Ni1 O9 106.08(15) . . ? N5 Ni1 O9 85.86(16) . . ? N5 C11 C12 122.1(6) . . ? N5 C11 C10 116.1(5) . . ? C12 C11 C10 121.7(5) . . ? C17 N1 C1 121.0(6) . . ? C17 N1 Ni1 121.7(4) . . ? C1 N1 Ni1 116.1(5) . . ? C2 N2 C3 113.5(5) . . ? C2 N2 Ni1 108.2(4) . . ? C3 N2 Ni1 117.8(4) . . ? C2 N2 H2C 105.4 . . ? C3 N2 H2C 105.4 . . ? Ni1 N2 H2C 105.4 . . ? N3 C9 C10 114.1(5) . . ? N3 C9 H9A 108.7 . . ? C10 C9 H9A 108.7 . . ? N3 C9 H9B 108.7 . . ? C10 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C1 C2 N2 110.8(5) . . ? C1 C2 H2A 109.5 . . ? N2 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? N1 C1 C20 119.3(7) . . ? N1 C1 C2 114.2(6) . . ? C20 C1 C2 126.6(7) . . ? C9 N3 C5 106.7(5) . . ? C9 N3 C6 107.7(5) . . ? C5 N3 C6 108.5(5) . . ? C9 N3 Ni1 111.5(3) . . ? C5 N3 Ni1 112.2(4) . . ? C6 N3 Ni1 110.1(3) . . ? C11 N5 C15 116.9(5) . . ? C11 N5 Ni1 121.9(4) . . ? C15 N5 Ni1 120.9(4) . . ? C14 C15 N5 123.6(6) . . ? C14 C15 H15 118.2 . . ? N5 C15 H15 118.2 . . ? C8 N4 Ni1 116.0(4) . . ? C8 N4 H4A 108.3 . . ? Ni1 N4 H4A 108.3 . . ? C8 N4 H4B 108.3 . . ? Ni1 N4 H4B 108.3 . . ? H4A N4 H4B 107.4 . . ? C11 C10 C9 112.8(5) . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? O2 Cl1 O1 114.9(7) . . ? O2 Cl1 O3 110.3(5) . . ? O1 Cl1 O3 106.1(5) . . ? O2 Cl1 O4 110.9(5) . . ? O1 Cl1 O4 104.0(6) . . ? O3 Cl1 O4 110.4(4) . . ? N3 C5 C4 116.3(5) . . ? N3 C5 H5A 108.2 . . ? C4 C5 H5A 108.2 . . ? N3 C5 H5B 108.2 . . ? C4 C5 H5B 108.2 . . ? H5A C5 H5B 107.4 . . ? O6 Cl2 O7 112.6(4) . . ? O6 Cl2 O8 116.5(4) . . ? O7 Cl2 O8 115.1(4) . . ? O6 Cl2 O5 104.9(5) . . ? O7 Cl2 O5 103.4(5) . . ? O8 Cl2 O5 102.3(4) . . ? C15 C14 C13 119.2(6) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C13 C12 C11 121.1(6) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C6 C7 C8 115.7(5) . . ? C6 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7B 108.3 . . ? C8 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? C12 C13 C14 117.0(6) . . ? C12 C13 H13 121.5 . . ? C14 C13 H13 121.5 . . ? C3 C4 C5 116.8(6) . . ? C3 C4 H4C 108.1 . . ? C5 C4 H4C 108.1 . . ? C3 C4 H4D 108.1 . . ? C5 C4 H4D 108.1 . . ? H4C C4 H4D 107.3 . . ? N2 C3 C4 110.9(5) . . ? N2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.0 . . ? C7 C6 N3 120.1(5) . . ? C7 C6 H6A 107.3 . . ? N3 C6 H6A 107.3 . . ? C7 C6 H6B 107.3 . . ? N3 C6 H6B 107.3 . . ? H6A C6 H6B 106.9 . . ? N4 C8 C7 112.6(5) . . ? N4 C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? N4 C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C18 C19 C20 122.2(8) . . ? C18 C19 H19 118.9 . . ? C20 C19 H19 118.9 . . ? O9 C16 C17 108.6(5) . . ? O9 C16 H16A 110.0 . . ? C17 C16 H16A 110.0 . . ? O9 C16 H16B 110.0 . . ? C17 C16 H16B 110.0 . . ? H16A C16 H16B 108.4 . . ? C19 C20 C1 118.3(7) . . ? C19 C20 H20 120.9 . . ? C1 C20 H20 120.9 . . ? N1 C17 C18 122.8(7) . . ? N1 C17 C16 116.4(6) . . ? C18 C17 C16 120.6(7) . . ? C19 C18 C17 116.3(7) . . ? C19 C18 H18 121.8 . . ? C17 C18 H18 121.8 . . ? H2S O1S H1S 62(6) . . ? 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 C16 O9 Ni1 N1 -19.1(5) . . . . ? C16 O9 Ni1 N2 -12.2(7) . . . . ? C16 O9 Ni1 N4 -109.8(5) . . . . ? C16 O9 Ni1 N3 162.5(5) . . . . ? C16 O9 Ni1 N5 70.4(5) . . . . ? N2 Ni1 N1 C17 -161.0(6) . . . . ? N4 Ni1 N1 C17 104.0(6) . . . . ? N3 Ni1 N1 C17 119(7) . . . . ? N5 Ni1 N1 C17 -70.3(6) . . . . ? O9 Ni1 N1 C17 15.9(5) . . . . ? N2 Ni1 N1 C1 6.9(5) . . . . ? N4 Ni1 N1 C1 -88.2(5) . . . . ? N3 Ni1 N1 C1 -73(7) . . . . ? N5 Ni1 N1 C1 97.6(5) . . . . ? O9 Ni1 N1 C1 -176.2(5) . . . . ? N1 Ni1 N2 C2 -23.1(4) . . . . ? N4 Ni1 N2 C2 66.2(4) . . . . ? N3 Ni1 N2 C2 155.3(4) . . . . ? N5 Ni1 N2 C2 -111.4(4) . . . . ? O9 Ni1 N2 C2 -29.9(6) . . . . ? N1 Ni1 N2 C3 -153.5(5) . . . . ? N4 Ni1 N2 C3 -64.1(5) . . . . ? N3 Ni1 N2 C3 25.0(5) . . . . ? N5 Ni1 N2 C3 118.2(5) . . . . ? O9 Ni1 N2 C3 -160.2(4) . . . . ? C3 N2 C2 C1 168.2(5) . . . . ? Ni1 N2 C2 C1 35.6(6) . . . . ? C17 N1 C1 C20 0.3(10) . . . . ? Ni1 N1 C1 C20 -167.7(5) . . . . ? C17 N1 C1 C2 179.7(6) . . . . ? Ni1 N1 C1 C2 11.7(7) . . . . ? N2 C2 C1 N1 -31.9(8) . . . . ? N2 C2 C1 C20 147.5(7) . . . . ? C10 C9 N3 C5 166.0(5) . . . . ? C10 C9 N3 C6 -77.7(6) . . . . ? C10 C9 N3 Ni1 43.1(6) . . . . ? N1 Ni1 N3 C9 177(100) . . . . ? N2 Ni1 N3 C9 97.8(4) . . . . ? N4 Ni1 N3 C9 -167.4(4) . . . . ? N5 Ni1 N3 C9 6.8(4) . . . . ? O9 Ni1 N3 C9 -79.8(4) . . . . ? N1 Ni1 N3 C5 58(7) . . . . ? N2 Ni1 N3 C5 -21.8(4) . . . . ? N4 Ni1 N3 C5 72.9(4) . . . . ? N5 Ni1 N3 C5 -112.9(4) . . . . ? O9 Ni1 N3 C5 160.6(4) . . . . ? N1 Ni1 N3 C6 -63(7) . . . . ? N2 Ni1 N3 C6 -142.7(4) . . . . ? N4 Ni1 N3 C6 -48.0(4) . . . . ? N5 Ni1 N3 C6 126.3(4) . . . . ? O9 Ni1 N3 C6 39.7(4) . . . . ? C12 C11 N5 C15 2.7(8) . . . . ? C10 C11 N5 C15 -174.8(5) . . . . ? C12 C11 N5 Ni1 -171.0(4) . . . . ? C10 C11 N5 Ni1 11.6(6) . . . . ? N1 Ni1 N5 C11 143.3(4) . . . . ? N2 Ni1 N5 C11 -136.9(4) . . . . ? N4 Ni1 N5 C11 66.4(19) . . . . ? N3 Ni1 N5 C11 -36.9(4) . . . . ? O9 Ni1 N5 C11 69.0(4) . . . . ? N1 Ni1 N5 C15 -30.0(4) . . . . ? N2 Ni1 N5 C15 49.8(4) . . . . ? N4 Ni1 N5 C15 -106.9(18) . . . . ? N3 Ni1 N5 C15 149.7(4) . . . . ? O9 Ni1 N5 C15 -104.4(4) . . . . ? C11 N5 C15 C14 -2.8(9) . . . . ? Ni1 N5 C15 C14 170.9(5) . . . . ? N1 Ni1 N4 C8 -127.1(4) . . . . ? N2 Ni1 N4 C8 153.1(4) . . . . ? N3 Ni1 N4 C8 53.3(4) . . . . ? N5 Ni1 N4 C8 -50(2) . . . . ? O9 Ni1 N4 C8 -52.9(4) . . . . ? N5 C11 C10 C9 50.6(7) . . . . ? C12 C11 C10 C9 -126.9(6) . . . . ? N3 C9 C10 C11 -86.2(7) . . . . ? C9 N3 C5 C4 -78.2(7) . . . . ? C6 N3 C5 C4 166.0(6) . . . . ? Ni1 N3 C5 C4 44.2(7) . . . . ? N5 C15 C14 C13 2.9(10) . . . . ? N5 C11 C12 C13 -2.8(10) . . . . ? C10 C11 C12 C13 174.5(6) . . . . ? C11 C12 C13 C14 2.8(11) . . . . ? C15 C14 C13 C12 -2.8(11) . . . . ? N3 C5 C4 C3 -74.9(8) . . . . ? C2 N2 C3 C4 -176.2(5) . . . . ? Ni1 N2 C3 C4 -48.4(7) . . . . ? C5 C4 C3 N2 73.9(7) . . . . ? C8 C7 C6 N3 -63.0(8) . . . . ? C9 N3 C6 C7 -176.4(6) . . . . ? C5 N3 C6 C7 -61.2(7) . . . . ? Ni1 N3 C6 C7 61.9(6) . . . . ? Ni1 N4 C8 C7 -62.8(6) . . . . ? C6 C7 C8 N4 59.5(8) . . . . ? Ni1 O9 C16 C17 19.5(8) . . . . ? C18 C19 C20 C1 -3.8(15) . . . . ? N1 C1 C20 C19 2.8(12) . . . . ? C2 C1 C20 C19 -176.5(8) . . . . ? C1 N1 C17 C18 -2.6(11) . . . . ? Ni1 N1 C17 C18 164.8(6) . . . . ? C1 N1 C17 C16 -177.2(7) . . . . ? Ni1 N1 C17 C16 -9.9(9) . . . . ? O9 C16 C17 N1 -7.3(10) . . . . ? O9 C16 C17 C18 177.9(7) . . . . ? C20 C19 C18 C17 1.7(14) . . . . ? N1 C17 C18 C19 1.6(13) . . . . ? C16 C17 C18 C19 176.0(8) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.341 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.055 #==END data_CuL1 _database_code_CSD 215954 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H22 Cl2 Cu N4 O8' _chemical_formula_weight 520.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 12.430(3) _cell_length_b 12.238(3) _cell_length_c 13.699(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.844(4) _cell_angle_gamma 90.00 _cell_volume 2053.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.685 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1068 _exptl_absorpt_coefficient_mu 1.376 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an LT-2 low-temperature apparatus operating at 213 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 30 s , such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.75 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing, (1995). The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 14520 _diffrn_reflns_av_R_equivalents 0.0687 _diffrn_reflns_av_sigmaI/netI 0.0744 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 28.31 _reflns_number_total 5115 _reflns_number_gt 3098 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.054, 1998)' _computing_data_reduction 'SAINT (BRUKER, V6.01, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 1998, V5.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.0753P)^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_number_reflns 5115 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0997 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1542 _refine_ls_wR_factor_gt 0.1379 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.007 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.28207(4) 0.57826(4) 0.16990(4) 0.03607(17) Uani 1 1 d . . . N1 N 0.1259(3) 0.5809(3) 0.1533(2) 0.0345(7) Uani 1 1 d . . . N2 N 0.2457(3) 0.6393(3) 0.0306(2) 0.0397(8) Uani 1 1 d . . . N3 N 0.4403(3) 0.6004(3) 0.1951(3) 0.0428(9) Uani 1 1 d . . . H3C H 0.4598 0.6653 0.2236 0.051 Uiso 1 1 d R . . N4 N 0.2621(3) 0.5186(3) 0.3032(2) 0.0367(8) Uani 1 1 d . . . C1 C 0.0722(3) 0.6253(3) 0.0713(3) 0.0363(9) Uani 1 1 d . . . C2 C -0.0401(4) 0.6408(4) 0.0629(4) 0.0488(11) Uani 1 1 d . . . H2A H -0.0804 0.6702 0.0055 0.059 Uiso 1 1 calc R . . C3 C -0.0905(4) 0.6116(4) 0.1418(4) 0.0593(14) Uani 1 1 d . . . H3A H -0.1655 0.6207 0.1370 0.071 Uiso 1 1 calc R . . C4 C -0.0302(4) 0.5689(4) 0.2278(4) 0.0529(12) Uani 1 1 d . . . H4A H -0.0635 0.5510 0.2815 0.063 Uiso 1 1 calc R . . C5 C 0.0802(3) 0.5538(3) 0.2318(3) 0.0410(10) Uani 1 1 d . . . C6 C 0.1448(4) 0.6559(4) 0.0006(3) 0.0404(10) Uani 1 1 d . . . C7 C 0.0949(4) 0.7052(5) -0.0968(3) 0.0595(14) Uani 1 1 d . . . H7A H 0.1512 0.7210 -0.1347 0.089 Uiso 1 1 calc R . . H7B H 0.0577 0.7715 -0.0854 0.089 Uiso 1 1 calc R . . H7C H 0.0438 0.6546 -0.1327 0.089 Uiso 1 1 calc R . . C8 C 0.3302(4) 0.6614(5) -0.0289(3) 0.0529(12) Uani 1 1 d . . . H8A H 0.3071 0.7227 -0.0724 0.063 Uiso 1 1 calc R . . H8B H 0.3369 0.5984 -0.0703 0.063 Uiso 1 1 calc R . . C9 C 0.4416(4) 0.6870(5) 0.0311(4) 0.0643(15) Uani 1 1 d . . . H9A H 0.4922 0.6978 -0.0147 0.077 Uiso 1 1 calc R . . H9B H 0.4364 0.7559 0.0651 0.077 Uiso 1 1 calc R . . C10 C 0.4896(4) 0.6044(4) 0.1060(3) 0.0524(12) Uani 1 1 d . . . H10A H 0.4829 0.5329 0.0751 0.063 Uiso 1 1 calc R . . H10B H 0.5669 0.6198 0.1253 0.063 Uiso 1 1 calc R . . C11 C 0.5005(4) 0.5316(4) 0.2729(3) 0.0493(11) Uani 1 1 d . . . H11A H 0.5764 0.5543 0.2848 0.059 Uiso 1 1 calc R . . H11B H 0.4979 0.4567 0.2495 0.059 Uiso 1 1 calc R . . C12 C 0.4585(4) 0.5349(5) 0.3691(3) 0.0557(13) Uani 1 1 d . . . H12A H 0.4501 0.6110 0.3859 0.067 Uiso 1 1 calc R . . H12B H 0.5147 0.5045 0.4197 0.067 Uiso 1 1 calc R . . C13 C 0.3529(4) 0.4774(4) 0.3766(3) 0.0486(11) Uani 1 1 d . . . H13A H 0.3614 0.3997 0.3665 0.058 Uiso 1 1 calc R . . H13B H 0.3361 0.4879 0.4425 0.058 Uiso 1 1 calc R . . C14 C 0.1620(4) 0.5100(4) 0.3155(3) 0.0428(10) Uani 1 1 d . . . C15 C 0.1239(4) 0.4583(5) 0.4023(4) 0.0638(15) Uani 1 1 d . . . H15A H 0.1859 0.4350 0.4494 0.096 Uiso 1 1 calc R . . H15B H 0.0789 0.3963 0.3804 0.096 Uiso 1 1 calc R . . H15C H 0.0824 0.5103 0.4329 0.096 Uiso 1 1 calc R . . Cl1 Cl 0.29703(10) 0.29054(10) 0.13010(9) 0.0511(3) Uani 1 1 d . . . O1 O 0.3026(4) 0.4005(3) 0.0927(3) 0.0743(11) Uani 1 1 d . . . O2 O 0.2930(4) 0.2169(4) 0.0521(4) 0.1040(16) Uani 1 1 d . . . O3 O 0.2020(4) 0.2852(4) 0.1699(4) 0.1095(17) Uani 1 1 d . . . O4 O 0.3894(4) 0.2719(3) 0.2008(4) 0.1102(19) Uani 1 1 d . . . Cl2 Cl 0.23870(8) 0.62463(9) 0.67594(8) 0.0393(3) Uani 1 1 d . . . O5 O 0.2944(3) 0.6022(3) 0.5955(3) 0.0644(10) Uani 1 1 d . . . O6 O 0.2478(2) 0.5348(3) 0.7432(3) 0.0553(9) Uani 1 1 d . . . O7 O 0.1262(2) 0.6458(3) 0.6383(3) 0.0635(10) Uani 1 1 d . . . O8 O 0.2858(3) 0.7200(3) 0.7280(2) 0.0532(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0306(3) 0.0448(3) 0.0322(3) 0.0000(2) 0.00361(18) 0.0046(2) N1 0.0314(17) 0.0316(18) 0.0388(18) -0.0002(16) 0.0014(14) -0.0043(15) N2 0.047(2) 0.042(2) 0.0298(17) -0.0022(15) 0.0048(15) 0.0047(17) N3 0.0319(18) 0.056(2) 0.0424(19) -0.0018(18) 0.0105(15) 0.0105(16) N4 0.0356(19) 0.039(2) 0.0343(17) -0.0002(16) 0.0029(15) -0.0025(15) C1 0.037(2) 0.030(2) 0.039(2) -0.0038(18) -0.0021(17) 0.0000(18) C2 0.038(2) 0.048(3) 0.056(3) 0.010(2) -0.006(2) -0.003(2) C3 0.028(2) 0.067(3) 0.081(4) 0.012(3) 0.002(2) -0.006(2) C4 0.037(2) 0.062(3) 0.060(3) 0.015(3) 0.009(2) -0.013(2) C5 0.035(2) 0.038(2) 0.047(2) 0.0049(19) -0.0023(19) -0.0101(18) C6 0.049(3) 0.039(2) 0.032(2) -0.0042(19) 0.0005(18) 0.004(2) C7 0.059(3) 0.072(4) 0.044(3) 0.011(3) -0.001(2) 0.008(3) C8 0.051(3) 0.072(3) 0.040(2) 0.000(2) 0.020(2) 0.004(2) C9 0.046(3) 0.090(4) 0.062(3) 0.020(3) 0.025(3) 0.013(3) C10 0.038(2) 0.071(3) 0.051(3) -0.003(2) 0.015(2) 0.001(2) C11 0.030(2) 0.064(3) 0.051(3) 0.003(2) 0.0018(19) 0.001(2) C12 0.038(3) 0.086(4) 0.041(2) 0.006(3) 0.001(2) 0.010(2) C13 0.043(3) 0.062(3) 0.037(2) 0.010(2) -0.0019(19) 0.002(2) C14 0.047(3) 0.042(3) 0.038(2) 0.005(2) 0.0020(19) -0.012(2) C15 0.043(3) 0.086(4) 0.060(3) 0.026(3) 0.002(2) -0.023(3) Cl1 0.0427(6) 0.0447(7) 0.0614(7) -0.0091(6) -0.0040(5) 0.0032(5) O1 0.104(3) 0.047(2) 0.067(2) -0.0028(19) 0.004(2) 0.014(2) O2 0.128(4) 0.069(3) 0.105(3) -0.048(3) -0.008(3) 0.003(3) O3 0.094(4) 0.108(4) 0.137(4) 0.014(3) 0.051(3) -0.006(3) O4 0.094(3) 0.070(3) 0.137(4) -0.018(3) -0.066(3) 0.025(2) Cl2 0.0312(5) 0.0408(6) 0.0477(6) 0.0069(5) 0.0118(4) -0.0023(4) O5 0.073(2) 0.067(2) 0.062(2) 0.0055(19) 0.037(2) 0.0077(19) O6 0.0428(18) 0.0512(19) 0.075(2) 0.0201(18) 0.0202(17) -0.0024(15) O7 0.0281(16) 0.064(2) 0.097(3) 0.017(2) 0.0060(17) -0.0005(15) O8 0.060(2) 0.053(2) 0.0460(17) 0.0090(16) 0.0061(15) -0.0174(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.916(3) . ? Cu1 N3 1.956(3) . ? Cu1 N4 2.021(3) . ? Cu1 N2 2.027(3) . ? N1 C1 1.321(5) . ? N1 C5 1.341(5) . ? N2 C6 1.268(5) . ? N2 C8 1.461(5) . ? N3 C10 1.457(5) . ? N3 C11 1.461(6) . ? N4 C14 1.287(5) . ? N4 C13 1.466(5) . ? C1 C2 1.394(6) . ? C1 C6 1.480(6) . ? C2 C3 1.385(7) . ? C3 C4 1.386(7) . ? C4 C5 1.376(6) . ? C5 C14 1.495(6) . ? C6 C7 1.499(6) . ? C8 C9 1.517(7) . ? C9 C10 1.491(7) . ? C11 C12 1.498(6) . ? C12 C13 1.508(6) . ? C14 C15 1.494(6) . ? Cl1 O3 1.385(5) . ? Cl1 O4 1.388(4) . ? Cl1 O2 1.392(4) . ? Cl1 O1 1.445(4) . ? Cl2 O5 1.425(3) . ? Cl2 O6 1.426(3) . ? Cl2 O7 1.429(3) . ? Cl2 O8 1.439(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 N1 Cu1 N3 170.43(15) . . ? N1 Cu1 N4 80.49(14) . . ? N3 Cu1 N4 99.55(14) . . ? N1 Cu1 N2 79.86(14) . . ? N3 Cu1 N2 99.80(15) . . ? N4 Cu1 N2 160.35(14) . . ? C1 N1 C5 124.2(4) . . ? C1 N1 Cu1 117.5(3) . . ? C5 N1 Cu1 117.4(3) . . ? C6 N2 C8 123.7(4) . . ? C6 N2 Cu1 114.4(3) . . ? C8 N2 Cu1 121.9(3) . . ? C10 N3 C11 113.2(3) . . ? C10 N3 Cu1 114.3(3) . . ? C11 N3 Cu1 115.0(3) . . ? C14 N4 C13 122.0(4) . . ? C14 N4 Cu1 114.7(3) . . ? C13 N4 Cu1 123.0(3) . . ? N1 C1 C2 118.6(4) . . ? N1 C1 C6 112.6(4) . . ? C2 C1 C6 128.7(4) . . ? C3 C2 C1 118.7(4) . . ? C2 C3 C4 120.6(4) . . ? C5 C4 C3 118.4(4) . . ? N1 C5 C4 119.4(4) . . ? N1 C5 C14 112.2(4) . . ? C4 C5 C14 128.4(4) . . ? N2 C6 C1 115.3(4) . . ? N2 C6 C7 126.1(4) . . ? C1 C6 C7 118.6(4) . . ? N2 C8 C9 114.4(4) . . ? C10 C9 C8 117.0(5) . . ? N3 C10 C9 115.0(4) . . ? N3 C11 C12 114.5(4) . . ? C11 C12 C13 119.0(4) . . ? N4 C13 C12 111.8(4) . . ? N4 C14 C15 125.7(4) . . ? N4 C14 C5 114.6(4) . . ? C15 C14 C5 119.7(4) . . ? O3 Cl1 O4 112.2(4) . . ? O3 Cl1 O2 110.5(3) . . ? O4 Cl1 O2 110.2(3) . . ? O3 Cl1 O1 106.2(3) . . ? O4 Cl1 O1 108.5(3) . . ? O2 Cl1 O1 109.2(3) . . ? O5 Cl2 O6 110.8(2) . . ? O5 Cl2 O7 109.3(2) . . ? O6 Cl2 O7 109.7(2) . . ? O5 Cl2 O8 109.2(2) . . ? O6 Cl2 O8 108.9(2) . . ? O7 Cl2 O8 108.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 N1 C1 83.6(9) . . . . ? N4 Cu1 N1 C1 174.6(3) . . . . ? N2 Cu1 N1 C1 -5.2(3) . . . . ? N3 Cu1 N1 C5 -86.1(9) . . . . ? N4 Cu1 N1 C5 4.9(3) . . . . ? N2 Cu1 N1 C5 -175.0(3) . . . . ? N1 Cu1 N2 C6 3.5(3) . . . . ? N3 Cu1 N2 C6 -166.8(3) . . . . ? N4 Cu1 N2 C6 3.1(6) . . . . ? N1 Cu1 N2 C8 -176.3(4) . . . . ? N3 Cu1 N2 C8 13.4(4) . . . . ? N4 Cu1 N2 C8 -176.7(4) . . . . ? N1 Cu1 N3 C10 -112.3(8) . . . . ? N4 Cu1 N3 C10 158.3(3) . . . . ? N2 Cu1 N3 C10 -25.2(3) . . . . ? N1 Cu1 N3 C11 114.2(9) . . . . ? N4 Cu1 N3 C11 24.8(3) . . . . ? N2 Cu1 N3 C11 -158.6(3) . . . . ? N1 Cu1 N4 C14 0.1(3) . . . . ? N3 Cu1 N4 C14 170.4(3) . . . . ? N2 Cu1 N4 C14 0.5(6) . . . . ? N1 Cu1 N4 C13 174.0(4) . . . . ? N3 Cu1 N4 C13 -15.7(4) . . . . ? N2 Cu1 N4 C13 174.4(4) . . . . ? C5 N1 C1 C2 -3.1(6) . . . . ? Cu1 N1 C1 C2 -172.0(3) . . . . ? C5 N1 C1 C6 174.8(4) . . . . ? Cu1 N1 C1 C6 5.9(4) . . . . ? N1 C1 C2 C3 1.6(7) . . . . ? C6 C1 C2 C3 -175.9(4) . . . . ? C1 C2 C3 C4 0.7(8) . . . . ? C2 C3 C4 C5 -1.7(8) . . . . ? C1 N1 C5 C4 2.1(6) . . . . ? Cu1 N1 C5 C4 171.1(3) . . . . ? C1 N1 C5 C14 -177.3(4) . . . . ? Cu1 N1 C5 C14 -8.4(5) . . . . ? C3 C4 C5 N1 0.3(7) . . . . ? C3 C4 C5 C14 179.7(5) . . . . ? C8 N2 C6 C1 178.4(4) . . . . ? Cu1 N2 C6 C1 -1.4(5) . . . . ? C8 N2 C6 C7 -3.2(7) . . . . ? Cu1 N2 C6 C7 176.9(4) . . . . ? N1 C1 C6 N2 -2.7(5) . . . . ? C2 C1 C6 N2 174.9(4) . . . . ? N1 C1 C6 C7 178.8(4) . . . . ? C2 C1 C6 C7 -3.6(7) . . . . ? C6 N2 C8 C9 152.9(5) . . . . ? Cu1 N2 C8 C9 -27.3(6) . . . . ? N2 C8 C9 C10 55.8(6) . . . . ? C11 N3 C10 C9 -170.7(4) . . . . ? Cu1 N3 C10 C9 55.0(5) . . . . ? C8 C9 C10 N3 -74.1(6) . . . . ? C10 N3 C11 C12 174.0(4) . . . . ? Cu1 N3 C11 C12 -52.0(5) . . . . ? N3 C11 C12 C13 73.5(6) . . . . ? C14 N4 C13 C12 -156.5(4) . . . . ? Cu1 N4 C13 C12 30.1(5) . . . . ? C11 C12 C13 N4 -58.0(6) . . . . ? C13 N4 C14 C15 -0.4(7) . . . . ? Cu1 N4 C14 C15 173.5(4) . . . . ? C13 N4 C14 C5 -178.4(4) . . . . ? Cu1 N4 C14 C5 -4.5(5) . . . . ? N1 C5 C14 N4 8.3(5) . . . . ? C4 C5 C14 N4 -171.1(4) . . . . ? N1 C5 C14 C15 -169.8(4) . . . . ? C4 C5 C14 C15 10.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.656 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.088 #==END data_CuL2 _database_code_CSD 215955 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H22 Cl2 Cu N4 O8' _chemical_formula_weight 520.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.832(5) _cell_length_b 7.288(4) _cell_length_c 13.925(8) _cell_angle_alpha 90.00 _cell_angle_beta 112.824(12) _cell_angle_gamma 90.00 _cell_volume 1013.2(9) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.707 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 534 _exptl_absorpt_coefficient_mu 1.394 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled devi ce) based diffractometer equipped with an LT-2 low-temperature apparatus operating at 213 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 30 s , such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.75 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing, (1995). The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. TWIN -1 0 0 0 -1 0 1 0 1 -4 BASF 0.21306 0.23196 0.27521 ; _diffrn_ambient_temperature 213(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 ? _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 6698 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4556 _reflns_number_gt 3884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.054, 1998)' _computing_data_reduction 'SAINT (BRUKER, V6.01, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 1998, V5.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.0889P)^2^+0.3616P] 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 0.00 _refine_ls_number_reflns 4556 _refine_ls_number_parameters 354 _refine_ls_number_restraints 376 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1362 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 2.158 _refine_ls_shift/su_mean 0.015 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 0.16149(4) 0.46289(12) 0.78294(3) 0.05072(9) Uani 1 1 d U . . N1 N 0.0309(3) 0.4661(13) 0.6468(2) 0.0620(8) Uani 1 1 d U A . C1 C 0.0660(5) 0.4666(15) 0.5665(3) 0.0679(10) Uani 1 1 d U . . C2 C -0.0238(6) 0.4525(14) 0.4659(3) 0.0908(15) Uani 1 1 d U B . H2A H 0.0005 0.4350 0.4086 0.109 Uiso 1 1 calc R . . C3 C -0.1610(7) 0.468(2) 0.4576(5) 0.1102(19) Uani 1 1 d U . . H3A H -0.2279 0.4739 0.3900 0.132 Uiso 1 1 calc R B . C4 C -0.2034(5) 0.4741(19) 0.5399(6) 0.113(2) Uani 1 1 d U A . H4A H -0.2941 0.4805 0.5306 0.135 Uiso 1 1 calc R . . C5 C -0.0970(4) 0.4701(16) 0.6390(4) 0.0716(11) Uani 1 1 d U . . C6 C -0.0993(7) 0.450(3) 0.7442(9) 0.0816(17) Uani 0.50 1 d PDU A 1 C6B C -0.1220(7) 0.488(3) 0.7401(10) 0.0816(17) Uani 0.50 1 d PDU A 2 C7 C -0.2315(6) 0.522(2) 0.7423(9) 0.213(7) Uani 1 1 d DU . . H7A H -0.2350 0.5106 0.8099 0.320 Uiso 1 1 d R A . H7B H -0.2395 0.6495 0.7226 0.320 Uiso 1 1 d R . . H7C H -0.3038 0.4544 0.6923 0.320 Uiso 1 1 d R . . N2 N 0.0057(3) 0.4645(15) 0.8236(3) 0.0746(9) Uani 1 1 d DU A . C8 C 0.0112(6) 0.466(3) 0.9252(5) 0.135(3) Uani 1 1 d U . . H8A H -0.0204 0.5859 0.9381 0.162 Uiso 1 1 calc R B . H8B H -0.0515 0.3734 0.9304 0.162 Uiso 1 1 calc R . . C9 C 0.1358(8) 0.433(3) 1.0036(6) 0.147(4) Uani 1 1 d U B . H9A H 0.1423 0.5262 1.0560 0.177 Uiso 1 1 calc R . . H9B H 0.1232 0.3165 1.0337 0.177 Uiso 1 1 calc R . . C10 C 0.2603(8) 0.4213(10) 1.0080(4) 0.100(2) Uani 1 1 d U . . H10A H 0.2907 0.2966 1.0321 0.119 Uiso 1 1 calc R B . H10B H 0.3141 0.5039 1.0642 0.119 Uiso 1 1 calc R . . N3 N 0.3014(5) 0.4566(18) 0.9208(4) 0.1139(19) Uani 1 1 d U B . H3 H 0.301(9) 0.582(13) 0.929(8) 0.137 Uiso 1 1 calc . . . C11 C 0.4335(5) 0.452(2) 0.9319(5) 0.096(2) Uani 1 1 d U . . H11A H 0.4588 0.3225 0.9368 0.115 Uiso 1 1 calc R B . H11B H 0.4854 0.5065 1.0001 0.115 Uiso 1 1 calc R . . C12 C 0.4879(6) 0.5419(12) 0.8532(6) 0.105(3) Uani 1 1 d U B . H12A H 0.4756 0.6750 0.8544 0.126 Uiso 1 1 calc R . . H12B H 0.5845 0.5188 0.8789 0.126 Uiso 1 1 calc R . . C13 C 0.4289(5) 0.4819(17) 0.7469(5) 0.0918(19) Uani 1 1 d U . . H13A H 0.4643 0.3597 0.7429 0.110 Uiso 1 1 calc R B . H13B H 0.4593 0.5646 0.7050 0.110 Uiso 1 1 calc R . . N4 N 0.2792(3) 0.4722(12) 0.6975(3) 0.0647(9) Uani 1 1 d U B . C14 C 0.2210(5) 0.4665(17) 0.6032(4) 0.0744(11) Uani 1 1 d U B . C15 C 0.2807(6) 0.4384(10) 0.5252(5) 0.0965(16) Uani 1 1 d U . . H15A H 0.3766 0.4402 0.5592 0.145 Uiso 1 1 d R B . H15B H 0.2526 0.3242 0.4889 0.145 Uiso 1 1 d R . . H15C H 0.2516 0.5381 0.4765 0.145 Uiso 1 1 d R . . Cl1 Cl 0.15241(8) 0.9632(3) 0.83021(6) 0.05186(19) Uani 0.313(4) 1 d PDU B 1 O1 O 0.2207(8) 0.8160(10) 0.8129(7) 0.063(3) Uani 0.313(4) 1 d PDU B 1 O2 O 0.1966(10) 0.9898(18) 0.9332(5) 0.099(4) Uani 0.313(4) 1 d PDU B 1 O3 O 0.0264(5) 0.9315(11) 0.7904(5) 0.061(2) Uani 0.313(4) 1 d PDU B 1 O4 O 0.1895(8) 1.1076(10) 0.7877(7) 0.068(3) Uani 0.313(4) 1 d PDU B 1 Cl1' Cl 0.15241(8) 0.9632(3) 0.83021(6) 0.05186(19) Uani 0.687(4) 1 d PDU B 2 O1' O 0.1289(12) 1.1093(7) 0.7724(5) 0.124(3) Uani 0.687(4) 1 d PDU B 2 O2' O 0.2337(12) 0.9350(13) 0.9327(5) 0.172(4) Uani 0.687(4) 1 d PU B 2 O3' O 0.0295(6) 0.987(3) 0.8411(7) 0.170(4) Uani 0.687(4) 1 d PU B 2 O4' O 0.1659(10) 0.7893(9) 0.7738(6) 0.098(2) Uani 0.687(4) 1 d PU B 2 Cl2 Cl 0.43711(14) 0.4724(6) 0.32185(10) 0.1007(5) Uani 0.347(5) 1 d PDU C 1 O5 O 0.3641(10) 0.6201(13) 0.3173(10) 0.173(6) Uani 0.347(5) 1 d PDU C 1 O6 O 0.4973(9) 0.4111(18) 0.4168(6) 0.116(5) Uani 0.347(5) 1 d PDU C 1 O7 O 0.5202(9) 0.503(2) 0.2746(7) 0.120(4) Uani 0.347(5) 1 d PDU C 1 O8 O 0.3640(17) 0.3460(14) 0.2570(9) 0.152(5) Uani 0.347(5) 1 d PDU C 1 Cl2' Cl 0.43711(14) 0.4724(6) 0.32185(10) 0.1007(5) Uani 0.653(5) 1 d PU C 2 O5' O 0.5127(9) 0.444(3) 0.2619(8) 0.158(3) Uani 0.653(5) 1 d PU C 2 O6' O 0.4705(10) 0.6055(14) 0.3938(7) 0.109(2) Uani 0.653(5) 1 d PU C 2 O7' O 0.4729(16) 0.2850(18) 0.3865(10) 0.173(5) Uani 0.653(5) 1 d PU C 2 O8' O 0.2978(7) 0.441(3) 0.2664(7) 0.121(3) Uani 0.653(5) 1 d PU C 2 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 0.05935(17) 0.05110(17) 0.04208(14) 0.0009(5) 0.02010(14) 0.0006(7) N1 0.0622(15) 0.0583(15) 0.0568(13) -0.002(4) 0.0136(11) 0.005(5) C1 0.103(2) 0.0484(16) 0.0440(13) 0.006(4) 0.0198(16) 0.003(6) C2 0.124(3) 0.078(3) 0.0538(18) 0.012(4) 0.015(2) -0.005(7) C3 0.105(3) 0.103(4) 0.076(3) 0.021(8) -0.016(2) -0.009(10) C4 0.059(2) 0.117(5) 0.135(3) 0.045(6) 0.007(2) -0.002(6) C5 0.0524(16) 0.047(2) 0.099(2) -0.003(6) 0.0122(15) 0.000(5) C6 0.0517(18) 0.066(4) 0.138(2) -0.016(7) 0.0494(18) -0.004(5) C6B 0.0517(18) 0.066(4) 0.138(2) -0.016(7) 0.0494(18) -0.004(5) C7 0.081(2) 0.316(19) 0.271(7) -0.023(10) 0.100(3) 0.065(6) N2 0.0701(12) 0.076(2) 0.1046(16) -0.013(4) 0.0633(11) 0.010(4) C8 0.153(3) 0.179(7) 0.120(2) -0.008(8) 0.105(2) 0.038(8) C9 0.142(4) 0.216(11) 0.095(3) -0.030(7) 0.058(3) -0.077(7) C10 0.151(3) 0.105(6) 0.0440(17) 0.014(2) 0.039(2) 0.031(4) N3 0.078(2) 0.176(5) 0.071(2) 0.060(4) 0.0106(17) -0.010(6) C11 0.066(2) 0.121(5) 0.080(3) 0.008(6) 0.007(2) 0.018(6) C12 0.050(3) 0.136(7) 0.111(4) 0.013(4) 0.010(3) -0.012(3) C13 0.075(2) 0.102(5) 0.111(3) 0.017(5) 0.050(2) 0.018(5) N4 0.0554(13) 0.0549(19) 0.0912(19) -0.023(3) 0.0365(13) -0.007(3) C14 0.0949(19) 0.060(2) 0.088(2) 0.021(5) 0.0568(16) 0.018(5) C15 0.160(3) 0.054(4) 0.116(3) -0.008(3) 0.099(2) -0.019(3) Cl1 0.0530(4) 0.0447(3) 0.0557(4) 0.0003(11) 0.0188(3) 0.0024(13) O1 0.061(4) 0.047(4) 0.074(6) -0.018(4) 0.019(5) 0.012(4) O2 0.106(6) 0.130(10) 0.070(4) 0.003(5) 0.042(4) 0.059(8) O3 0.081(3) 0.074(7) 0.054(3) 0.046(4) 0.056(2) 0.036(3) O4 0.088(5) 0.038(3) 0.107(6) 0.014(4) 0.068(5) 0.037(3) Cl1' 0.0530(4) 0.0447(3) 0.0557(4) 0.0003(11) 0.0188(3) 0.0024(13) O1' 0.247(8) 0.0200(19) 0.088(4) -0.004(2) 0.047(5) 0.003(4) O2' 0.219(7) 0.088(6) 0.093(3) -0.020(4) -0.067(5) 0.053(7) O3' 0.116(3) 0.247(10) 0.200(5) -0.041(7) 0.119(3) 0.036(6) O4' 0.188(5) 0.038(2) 0.098(3) -0.021(2) 0.088(4) -0.006(3) Cl2 0.0847(6) 0.1442(12) 0.0750(6) -0.0203(16) 0.0329(6) -0.0284(19) O5 0.125(7) 0.171(7) 0.228(16) 0.040(7) 0.074(8) 0.027(6) O6 0.052(5) 0.201(15) 0.097(5) 0.025(7) 0.030(4) -0.003(7) O7 0.175(5) 0.119(12) 0.098(5) -0.046(6) 0.090(4) -0.068(6) O8 0.164(10) 0.143(7) 0.106(8) 0.041(6) 0.004(9) -0.062(7) Cl2' 0.0847(6) 0.1442(12) 0.0750(6) -0.0203(16) 0.0329(6) -0.0284(19) O5' 0.121(4) 0.229(9) 0.140(4) -0.123(4) 0.068(3) -0.035(7) O6' 0.133(5) 0.117(4) 0.087(4) -0.016(3) 0.055(4) 0.024(5) O7' 0.183(10) 0.125(5) 0.142(8) 0.003(5) -0.011(6) 0.065(6) O8' 0.086(3) 0.150(9) 0.104(5) 0.023(7) 0.012(3) 0.009(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 N1 1.875(3) . ? Cu1 N3 1.930(4) . ? Cu1 N2 1.977(3) . ? Cu1 N4 2.055(4) . ? Cu1 O4' 2.384(7) . ? N1 C1 1.314(6) . ? N1 C5 1.347(6) . ? C1 C2 1.365(6) . ? C1 C14 1.554(7) . ? C2 C3 1.450(10) . ? C3 C4 1.391(11) . ? C4 C5 1.414(7) . ? C5 C6 1.482(14) . ? C5 C6B 1.539(15) . ? C6 N2 1.246(9) . ? C6 C7 1.517(14) . ? C6B C7 1.224(11) . ? C6B N2 1.431(9) . ? N2 C8 1.393(8) . ? C8 C9 1.389(11) . ? C9 C10 1.329(12) . ? C10 N3 1.470(9) . ? N3 C11 1.379(8) . ? C11 C12 1.573(13) . ? C12 C13 1.434(11) . ? C13 N4 1.498(6) . ? N4 C14 1.217(6) . ? C14 C15 1.477(9) . ? Cl1 O3 1.280(6) . ? Cl1 O2 1.338(6) . ? Cl1 O4 1.342(8) . ? Cl1 O1 1.376(7) . ? Cl2 O6 1.305(7) . ? Cl2 O8 1.317(9) . ? Cl2 O5 1.323(9) . ? Cl2 O7 1.324(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N3 177.6(3) . . ? N1 Cu1 N2 84.04(16) . . ? N3 Cu1 N2 98.3(2) . . ? N1 Cu1 N4 78.96(16) . . ? N3 Cu1 N4 98.8(2) . . ? N2 Cu1 N4 162.88(15) . . ? N1 Cu1 O4' 87.5(4) . . ? N3 Cu1 O4' 93.0(4) . . ? N2 Cu1 O4' 92.7(4) . . ? N4 Cu1 O4' 84.6(3) . . ? C1 N1 C5 124.0(4) . . ? C1 N1 Cu1 120.4(3) . . ? C5 N1 Cu1 115.6(3) . . ? N1 C1 C2 123.2(5) . . ? N1 C1 C14 110.7(3) . . ? C2 C1 C14 125.9(5) . . ? C1 C2 C3 112.1(6) . . ? C4 C3 C2 126.4(5) . . ? C3 C4 C5 113.5(5) . . ? N1 C5 C4 120.2(5) . . ? N1 C5 C6 109.2(4) . . ? C4 C5 C6 130.3(5) . . ? N1 C5 C6B 117.9(4) . . ? C4 C5 C6B 121.6(5) . . ? C6 C5 C6B 13.5(9) . . ? N2 C6 C5 120.7(8) . . ? N2 C6 C7 121.1(12) . . ? C5 C6 C7 109.0(9) . . ? C7 C6B N2 130.1(12) . . ? C7 C6B C5 123.8(10) . . ? N2 C6B C5 106.0(6) . . ? C6B C7 C6 8.8(12) . . ? C6 N2 C8 124.6(7) . . ? C6 N2 C6B 13.3(11) . . ? C8 N2 C6B 118.2(6) . . ? C6 N2 Cu1 109.4(6) . . ? C8 N2 Cu1 125.9(3) . . ? C6B N2 Cu1 115.5(6) . . ? C9 C8 N2 116.3(6) . . ? C10 C9 C8 135.0(8) . . ? C9 C10 N3 125.3(6) . . ? C11 N3 C10 122.5(5) . . ? C11 N3 Cu1 119.5(4) . . ? C10 N3 Cu1 117.0(4) . . ? N3 C11 C12 124.4(7) . . ? C13 C12 C11 117.1(7) . . ? C12 C13 N4 117.2(6) . . ? C14 N4 C13 120.8(5) . . ? C14 N4 Cu1 116.5(3) . . ? C13 N4 Cu1 122.7(4) . . ? N4 C14 C15 127.4(5) . . ? N4 C14 C1 113.3(4) . . ? C15 C14 C1 118.9(4) . . ? O3 Cl1 O2 111.6(5) . . ? O3 Cl1 O4 113.7(5) . . ? O2 Cl1 O4 108.4(6) . . ? O3 Cl1 O1 109.8(5) . . ? O2 Cl1 O1 107.9(6) . . ? O4 Cl1 O1 105.1(5) . . ? O6 Cl2 O8 112.7(7) . . ? O6 Cl2 O5 112.4(7) . . ? O8 Cl2 O5 110.3(8) . . ? O6 Cl2 O7 113.2(6) . . ? O8 Cl2 O7 97.1(10) . . ? O5 Cl2 O7 110.2(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 N1 C1 -16(12) . . . . ? N2 Cu1 N1 C1 180.0(10) . . . . ? N4 Cu1 N1 C1 2.0(9) . . . . ? O4' Cu1 N1 C1 87.0(9) . . . . ? N3 Cu1 N1 C5 165(11) . . . . ? N2 Cu1 N1 C5 0.8(9) . . . . ? N4 Cu1 N1 C5 -177.2(9) . . . . ? O4' Cu1 N1 C5 -92.2(9) . . . . ? C5 N1 C1 C2 -6.9(18) . . . . ? Cu1 N1 C1 C2 174.0(8) . . . . ? C5 N1 C1 C14 178.5(10) . . . . ? Cu1 N1 C1 C14 -0.6(13) . . . . ? N1 C1 C2 C3 9.5(16) . . . . ? C14 C1 C2 C3 -176.6(11) . . . . ? C1 C2 C3 C4 -7(2) . . . . ? C2 C3 C4 C5 2(2) . . . . ? C1 N1 C5 C4 0.4(19) . . . . ? Cu1 N1 C5 C4 179.5(10) . . . . ? C1 N1 C5 C6 174.6(13) . . . . ? Cu1 N1 C5 C6 -6.3(14) . . . . ? C1 N1 C5 C6B -174.1(12) . . . . ? Cu1 N1 C5 C6B 5.0(15) . . . . ? C3 C4 C5 N1 1.9(19) . . . . ? C3 C4 C5 C6 -171.0(16) . . . . ? C3 C4 C5 C6B 176.2(13) . . . . ? N1 C5 C6 N2 12(2) . . . . ? C4 C5 C6 N2 -174.2(15) . . . . ? C6B C5 C6 N2 -120(5) . . . . ? N1 C5 C6 C7 159.4(12) . . . . ? C4 C5 C6 C7 -27(2) . . . . ? C6B C5 C6 C7 27(3) . . . . ? N1 C5 C6B C7 167.8(16) . . . . ? C4 C5 C6B C7 -7(2) . . . . ? C6 C5 C6B C7 -140(4) . . . . ? N1 C5 C6B N2 -9.7(17) . . . . ? C4 C5 C6B N2 175.8(12) . . . . ? C6 C5 C6B N2 42(3) . . . . ? N2 C6B C7 C6 -76(5) . . . . ? C5 C6B C7 C6 107(6) . . . . ? N2 C6 C7 C6B 86(6) . . . . ? C5 C6 C7 C6B -61(5) . . . . ? C5 C6 N2 C8 173.3(16) . . . . ? C7 C6 N2 C8 30(3) . . . . ? C5 C6 N2 C6B 108(5) . . . . ? C7 C6 N2 C6B -35(4) . . . . ? C5 C6 N2 Cu1 -12(2) . . . . ? C7 C6 N2 Cu1 -154.7(14) . . . . ? C7 C6B N2 C6 128(5) . . . . ? C5 C6B N2 C6 -55(4) . . . . ? C7 C6B N2 C8 6(3) . . . . ? C5 C6B N2 C8 -177.1(13) . . . . ? C7 C6B N2 Cu1 -167.3(18) . . . . ? C5 C6B N2 Cu1 10.0(15) . . . . ? N1 Cu1 N2 C6 6.0(13) . . . . ? N3 Cu1 N2 C6 -173.4(13) . . . . ? N4 Cu1 N2 C6 13(2) . . . . ? O4' Cu1 N2 C6 93.2(13) . . . . ? N1 Cu1 N2 C8 -179.0(14) . . . . ? N3 Cu1 N2 C8 1.6(14) . . . . ? N4 Cu1 N2 C8 -172.1(14) . . . . ? O4' Cu1 N2 C8 -91.8(13) . . . . ? N1 Cu1 N2 C6B -6.8(11) . . . . ? N3 Cu1 N2 C6B 173.9(11) . . . . ? N4 Cu1 N2 C6B 0(2) . . . . ? O4' Cu1 N2 C6B 80.4(11) . . . . ? C6 N2 C8 C9 163.0(18) . . . . ? C6B N2 C8 C9 176.7(16) . . . . ? Cu1 N2 C8 C9 -11(2) . . . . ? N2 C8 C9 C10 10(3) . . . . ? C8 C9 C10 N3 5(3) . . . . ? C9 C10 N3 C11 176.2(15) . . . . ? C9 C10 N3 Cu1 -15.5(16) . . . . ? N1 Cu1 N3 C11 15(13) . . . . ? N2 Cu1 N3 C11 179.4(12) . . . . ? N4 Cu1 N3 C11 -2.5(13) . . . . ? O4' Cu1 N3 C11 -87.5(13) . . . . ? N1 Cu1 N3 C10 -154(11) . . . . ? N2 Cu1 N3 C10 10.8(9) . . . . ? N4 Cu1 N3 C10 -171.1(8) . . . . ? O4' Cu1 N3 C10 103.9(9) . . . . ? C10 N3 C11 C12 -161.6(10) . . . . ? Cu1 N3 C11 C12 30.5(19) . . . . ? N3 C11 C12 C13 -57.6(17) . . . . ? C11 C12 C13 N4 47.1(13) . . . . ? C12 C13 N4 C14 162.1(11) . . . . ? C12 C13 N4 Cu1 -19.1(14) . . . . ? N1 Cu1 N4 C14 -3.5(9) . . . . ? N3 Cu1 N4 C14 175.8(10) . . . . ? N2 Cu1 N4 C14 -10.5(18) . . . . ? O4' Cu1 N4 C14 -92.0(9) . . . . ? N1 Cu1 N4 C13 177.7(9) . . . . ? N3 Cu1 N4 C13 -3.1(9) . . . . ? N2 Cu1 N4 C13 170.7(12) . . . . ? O4' Cu1 N4 C13 89.2(8) . . . . ? C13 N4 C14 C15 10.5(19) . . . . ? Cu1 N4 C14 C15 -168.4(8) . . . . ? C13 N4 C14 C1 -177.2(9) . . . . ? Cu1 N4 C14 C1 4.0(13) . . . . ? N1 C1 C14 N4 -2.3(15) . . . . ? C2 C1 C14 N4 -176.8(11) . . . . ? N1 C1 C14 C15 170.7(9) . . . . ? C2 C1 C14 C15 -3.8(17) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 1.638 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.092