# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_abdun3o _database_code_depnum_ccdc_archive 'CCDC 888732' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 N3 O5' _chemical_formula_sum 'C12 H13 N3 O5' _chemical_formula_weight 279.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) _symmetry_space_group_name_Hall 'P 2c -2n' 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 10.1175(11) _cell_length_b 25.335(3) _cell_length_c 5.0430(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1292.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 1095 _cell_measurement_theta_min 3.4862 _cell_measurement_theta_max 62.9723 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.967 _exptl_absorpt_correction_T_min 0.22363 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'oxford gemini s' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 5 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4032 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 63.07 _reflns_number_total 1633 _reflns_number_gt 1181 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1030P)^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 0.0(5) _refine_ls_number_reflns 1633 _refine_ls_number_parameters 193 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1521 _refine_ls_wR_factor_gt 0.1448 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2417(5) 0.6834(2) 0.7874(11) 0.0299(12) Uani 1 1 d . . . C2 C 0.3471(5) 0.6786(2) 1.0074(11) 0.0320(12) Uani 1 1 d . . . C3 C 0.2084(5) 0.52717(19) 0.2349(10) 0.0266(11) Uani 1 1 d . . . C4 C 0.3115(5) 0.4845(2) 0.3042(10) 0.0262(11) Uani 1 1 d . . . C5 C 0.0593(5) 0.63377(18) 0.5962(10) 0.0276(12) Uani 1 1 d . . . C6 C -0.0388(5) 0.6711(2) 0.5861(11) 0.0368(13) Uani 1 1 d . . . H6 H -0.0353 0.7002 0.6984 0.044 Uiso 1 1 calc R . . C7 C -0.1433(5) 0.6657(2) 0.4095(13) 0.0381(14) Uani 1 1 d . . . H7 H -0.2087 0.6915 0.4006 0.046 Uiso 1 1 calc R . . C8 C -0.1490(5) 0.6218(2) 0.2470(11) 0.0366(13) Uani 1 1 d . . . H8 H -0.2186 0.6182 0.1278 0.044 Uiso 1 1 calc R . . C9 C -0.0539(5) 0.58365(19) 0.2593(11) 0.0318(12) Uani 1 1 d . . . H9 H -0.0608 0.5538 0.1529 0.038 Uiso 1 1 calc R . . C10 C 0.0527(5) 0.58910(18) 0.4289(10) 0.0267(11) Uani 1 1 d . . . C11 C 0.5314(6) 0.7164(3) 1.2050(13) 0.0545(18) Uani 1 1 d . . . H11A H 0.5850 0.7476 1.1930 0.082 Uiso 1 1 calc R . . H11B H 0.5852 0.6858 1.1737 0.082 Uiso 1 1 calc R . . H11C H 0.4930 0.7143 1.3788 0.082 Uiso 1 1 calc R . . C12 C 0.4635(5) 0.4204(2) 0.1315(13) 0.0362(12) Uani 1 1 d . . . H12A H 0.4914 0.4080 -0.0395 0.054 Uiso 1 1 calc R . . H12B H 0.4256 0.3917 0.2297 0.054 Uiso 1 1 calc R . . H12C H 0.5384 0.4341 0.2261 0.054 Uiso 1 1 calc R . . N1 N 0.1672(4) 0.63975(17) 0.7729(9) 0.0272(10) Uani 1 1 d . . . N2 N 0.1535(4) 0.54992(16) 0.4441(8) 0.0277(10) Uani 1 1 d D . . N3 N 0.3654(4) 0.46191(17) 0.0986(9) 0.0319(10) Uani 1 1 d . . . O1 O 0.2312(4) 0.72295(14) 0.6543(8) 0.0437(11) Uani 1 1 d . . . O2 O 0.3526(4) 0.64051(15) 1.1539(7) 0.0408(10) Uani 1 1 d . . . O3 O 0.4281(4) 0.71878(15) 1.0098(8) 0.0438(10) Uani 1 1 d . . . O4 O 0.1823(3) 0.53671(14) -0.0022(7) 0.0324(9) Uani 1 1 d . . . O5 O 0.3371(3) 0.47507(14) 0.5391(7) 0.0329(9) Uani 1 1 d . . . H1N H 0.187(6) 0.612(3) 0.884(13) 0.045(17) Uiso 1 1 d . . . H2N H 0.179(4) 0.5417(18) 0.611(5) 0.017(12) Uiso 1 1 d D . . H3N H 0.348(5) 0.473(2) -0.100(12) 0.029(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 C1 0.032(3) 0.029(3) 0.028(3) -0.006(2) -0.006(2) 0.001(2) C2 0.029(3) 0.035(3) 0.031(3) -0.004(3) -0.007(2) -0.002(2) C3 0.036(3) 0.022(3) 0.022(3) 0.000(2) -0.002(2) -0.007(2) C4 0.036(3) 0.025(2) 0.018(3) -0.003(2) 0.003(2) -0.004(2) C5 0.031(3) 0.026(3) 0.026(3) 0.003(2) -0.003(2) -0.003(2) C6 0.045(3) 0.030(3) 0.035(3) -0.005(3) -0.002(3) 0.005(3) C7 0.037(3) 0.027(3) 0.051(4) -0.005(3) -0.014(3) 0.011(2) C8 0.035(3) 0.038(3) 0.036(3) -0.002(3) -0.009(3) 0.000(2) C9 0.041(3) 0.027(3) 0.027(3) -0.001(2) -0.006(3) -0.004(2) C10 0.034(3) 0.025(3) 0.021(3) 0.002(2) 0.005(2) 0.002(2) C11 0.052(3) 0.054(4) 0.057(5) 0.005(3) -0.023(3) -0.006(3) C12 0.041(3) 0.035(3) 0.032(3) 0.003(3) 0.005(3) 0.010(3) N1 0.032(2) 0.024(2) 0.025(3) 0.002(2) -0.007(2) 0.0024(18) N2 0.041(3) 0.027(2) 0.015(2) -0.0003(19) 0.0036(19) 0.0025(19) N3 0.047(2) 0.033(2) 0.016(3) -0.0062(19) 0.003(2) 0.005(2) O1 0.056(2) 0.031(2) 0.045(2) 0.0161(19) -0.018(2) -0.0067(18) O2 0.056(2) 0.035(2) 0.031(2) 0.008(2) -0.0153(17) -0.0041(18) O3 0.047(2) 0.040(2) 0.045(2) 0.008(2) -0.0179(19) -0.0123(18) O4 0.051(2) 0.0300(19) 0.016(2) 0.0030(16) -0.0006(17) 0.0023(16) O5 0.048(2) 0.036(2) 0.014(2) 0.0058(16) -0.0013(15) 0.0037(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 C1 O1 1.211(6) . ? C1 N1 1.340(6) . ? C1 C2 1.544(7) . ? C2 O2 1.216(6) . ? C2 O3 1.308(6) . ? C3 O4 1.248(6) . ? C3 N2 1.324(7) . ? C3 C4 1.543(7) . ? C4 O5 1.236(6) . ? C4 N3 1.303(7) . ? C5 C6 1.371(7) . ? C5 C10 1.413(7) . ? C5 N1 1.417(6) . ? C6 C7 1.389(8) . ? C6 H6 0.9300 . ? C7 C8 1.383(8) . ? C7 H7 0.9300 . ? C8 C9 1.366(8) . ? C8 H8 0.9300 . ? C9 C10 1.383(7) . ? C9 H9 0.9300 . ? C10 N2 1.425(6) . ? C11 O3 1.437(7) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N3 1.456(7) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? N1 H1N 0.91(7) . ? N2 H2N 0.90(2) . ? N3 H3N 1.06(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 O1 C1 N1 127.1(5) . . ? O1 C1 C2 121.6(4) . . ? N1 C1 C2 111.3(5) . . ? O2 C2 O3 125.7(5) . . ? O2 C2 C1 122.1(4) . . ? O3 C2 C1 112.2(5) . . ? O4 C3 N2 126.2(5) . . ? O4 C3 C4 119.7(4) . . ? N2 C3 C4 114.1(4) . . ? O5 C4 N3 126.2(5) . . ? O5 C4 C3 119.6(4) . . ? N3 C4 C3 114.2(4) . . ? C6 C5 C10 119.7(5) . . ? C6 C5 N1 120.5(4) . . ? C10 C5 N1 119.8(4) . . ? C5 C6 C7 120.5(5) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 119.3(5) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C9 C8 C7 120.9(5) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.4(5) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C5 119.1(4) . . ? C9 C10 N2 121.4(5) . . ? C5 C10 N2 119.4(4) . . ? O3 C11 H11A 109.5 . . ? O3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 N1 C5 123.8(4) . . ? C1 N1 H1N 118(4) . . ? C5 N1 H1N 118(4) . . ? C3 N2 C10 124.1(5) . . ? C3 N2 H2N 121(3) . . ? C10 N2 H2N 115(3) . . ? C4 N3 C12 120.7(5) . . ? C4 N3 H3N 125(3) . . ? C12 N3 H3N 114(3) . . ? C2 O3 C11 115.5(4) . . ? 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 O1 C1 C2 O2 174.9(6) . . . . ? N1 C1 C2 O2 -3.9(7) . . . . ? O1 C1 C2 O3 -6.7(7) . . . . ? N1 C1 C2 O3 174.5(4) . . . . ? O4 C3 C4 O5 -180.0(5) . . . . ? N2 C3 C4 O5 -1.1(6) . . . . ? O4 C3 C4 N3 0.9(7) . . . . ? N2 C3 C4 N3 179.8(4) . . . . ? C10 C5 C6 C7 -1.2(8) . . . . ? N1 C5 C6 C7 178.8(5) . . . . ? C5 C6 C7 C8 1.3(9) . . . . ? C6 C7 C8 C9 0.4(9) . . . . ? C7 C8 C9 C10 -2.2(9) . . . . ? C8 C9 C10 C5 2.3(7) . . . . ? C8 C9 C10 N2 -179.7(5) . . . . ? C6 C5 C10 C9 -0.6(7) . . . . ? N1 C5 C10 C9 179.5(4) . . . . ? C6 C5 C10 N2 -178.7(5) . . . . ? N1 C5 C10 N2 1.3(7) . . . . ? O1 C1 N1 C5 -1.4(9) . . . . ? C2 C1 N1 C5 177.4(4) . . . . ? C6 C5 N1 C1 -52.0(7) . . . . ? C10 C5 N1 C1 127.9(5) . . . . ? O4 C3 N2 C10 1.0(8) . . . . ? C4 C3 N2 C10 -177.8(4) . . . . ? C9 C10 N2 C3 44.7(7) . . . . ? C5 C10 N2 C3 -137.2(5) . . . . ? O5 C4 N3 C12 1.6(8) . . . . ? C3 C4 N3 C12 -179.3(4) . . . . ? O2 C2 O3 C11 0.0(8) . . . . ? C1 C2 O3 C11 -178.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 63.07 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.313 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.074 data_abdul311 _database_code_depnum_ccdc_archive 'CCDC 888733' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 N2 O6, 2(C2 H6 O S)' _chemical_formula_sum 'C16 H24 N2 O8 S2' _chemical_formula_weight 436.49 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' 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.3163(5) _cell_length_b 9.0186(3) _cell_length_c 14.8471(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.034(4) _cell_angle_gamma 90.00 _cell_volume 2030.72(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 1780 _cell_measurement_theta_min 3.5733 _cell_measurement_theta_max 24.9955 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.308 _exptl_absorpt_correction_T_min 0.87818 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 'oxford gemini s' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 2 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3450 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1790 _reflns_number_gt 1516 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0378P)^2^+0.5664P] 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 1790 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0720 _refine_ls_wR_factor_gt 0.0703 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.07527(9) 0.55156(18) -0.08991(10) 0.0149(3) Uani 1 1 d . . . C2 C 0.06963(10) 0.71447(18) -0.06218(9) 0.0156(3) Uani 1 1 d . . . C3 C 0.00713(9) 0.37579(18) -0.20219(10) 0.0147(3) Uani 1 1 d . . . C4 C 0.01637(9) 0.24172(18) -0.15578(11) 0.0174(3) Uani 1 1 d . . . H4 H 0.0279 0.2413 -0.0926 0.021 Uiso 1 1 calc R . . C5 C 0.00858(10) 0.10922(19) -0.20269(11) 0.0198(4) Uani 1 1 d . . . H5 H 0.0148 0.0199 -0.1711 0.024 Uiso 1 1 calc R . . C6 C 0.15097(11) 0.91371(19) 0.00932(11) 0.0237(4) Uani 1 1 d . . . H6A H 0.2089 0.9353 0.0403 0.035 Uiso 1 1 calc R . . H6B H 0.1081 0.9322 0.0494 0.035 Uiso 1 1 calc R . . H6C H 0.1388 0.9758 -0.0434 0.035 Uiso 1 1 calc R . . C7 C 0.28162(11) 0.1738(2) 0.28814(11) 0.0275(4) Uani 1 1 d . . . H7A H 0.2721 0.1337 0.3459 0.041 Uiso 1 1 calc R . . H7B H 0.3082 0.2701 0.2970 0.041 Uiso 1 1 calc R . . H7C H 0.3200 0.1094 0.2604 0.041 Uiso 1 1 calc R . . C8 C 0.22003(12) 0.2636(2) 0.11910(11) 0.0286(4) Uani 1 1 d . . . H8A H 0.1720 0.2799 0.0713 0.043 Uiso 1 1 calc R . . H8B H 0.2610 0.1950 0.0988 0.043 Uiso 1 1 calc R . . H8C H 0.2493 0.3560 0.1351 0.043 Uiso 1 1 calc R . . N1 N 0.00967(8) 0.51329(15) -0.15587(8) 0.0143(3) Uani 1 1 d . . . O1 O 0.13378(7) 0.47041(13) -0.05432(7) 0.0225(3) Uani 1 1 d . . . O2 O 0.00408(7) 0.78889(13) -0.07717(7) 0.0197(3) Uani 1 1 d . . . O3 O 0.14657(7) 0.75969(13) -0.01826(7) 0.0208(3) Uani 1 1 d . . . O4 O 0.12999(7) 0.31403(14) 0.25482(7) 0.0244(3) Uani 1 1 d . . . S1 S 0.17875(2) 0.18927(5) 0.21605(3) 0.01868(14) Uani 1 1 d . . . H1N H -0.0245(11) 0.580(2) -0.1788(10) 0.014(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 C1 0.0145(7) 0.0176(8) 0.0127(7) 0.0014(6) 0.0027(6) -0.0008(7) C2 0.0170(8) 0.0192(9) 0.0104(7) 0.0009(6) 0.0013(6) -0.0019(7) C3 0.0098(7) 0.0167(8) 0.0179(7) -0.0015(7) 0.0024(6) -0.0003(6) C4 0.0140(7) 0.0200(9) 0.0179(7) 0.0028(7) 0.0011(6) -0.0010(7) C5 0.0176(8) 0.0154(9) 0.0253(8) 0.0043(7) -0.0004(7) 0.0006(7) C6 0.0241(8) 0.0168(9) 0.0291(9) -0.0059(7) 0.0004(7) -0.0032(8) C7 0.0200(8) 0.0313(11) 0.0304(9) 0.0001(8) 0.0010(7) 0.0061(8) C8 0.0316(9) 0.0315(11) 0.0248(9) 0.0033(8) 0.0115(7) 0.0084(9) N1 0.0140(7) 0.0135(7) 0.0148(6) 0.0006(6) 0.0004(5) 0.0016(6) O1 0.0213(6) 0.0192(6) 0.0247(6) 0.0001(5) -0.0045(5) 0.0031(5) O2 0.0185(6) 0.0185(6) 0.0217(6) -0.0009(5) 0.0010(5) 0.0021(5) O3 0.0183(5) 0.0196(6) 0.0231(6) -0.0061(5) -0.0023(5) -0.0006(5) O4 0.0223(6) 0.0309(7) 0.0204(6) -0.0024(5) 0.0040(5) 0.0120(5) S1 0.0149(2) 0.0200(2) 0.0211(2) -0.00097(17) 0.00260(16) 0.00225(17) _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 C1 O1 1.2188(17) . ? C1 N1 1.3463(18) . ? C1 C2 1.531(2) . ? C2 O2 1.2023(18) . ? C2 O3 1.3287(17) . ? C3 C4 1.389(2) . ? C3 C3 1.406(3) 2_554 ? C3 N1 1.416(2) . ? C4 C5 1.380(2) . ? C4 H4 0.9300 . ? C5 C5 1.393(3) 2_554 ? C5 H5 0.9300 . ? C6 O3 1.447(2) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 S1 1.7821(16) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 S1 1.7819(17) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N1 H1N 0.835(17) . ? O4 S1 1.5084(12) . ? 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 O1 C1 N1 126.16(15) . . ? O1 C1 C2 121.68(13) . . ? N1 C1 C2 112.16(13) . . ? O2 C2 O3 125.45(15) . . ? O2 C2 C1 124.24(13) . . ? O3 C2 C1 110.30(13) . . ? C4 C3 C3 119.45(9) . 2_554 ? C4 C3 N1 121.83(13) . . ? C3 C3 N1 118.71(8) 2_554 . ? C5 C4 C3 120.51(14) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C5 120.00(9) . 2_554 ? C4 C5 H5 120.0 . . ? C5 C5 H5 120.0 2_554 . ? O3 C6 H6A 109.5 . . ? O3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? S1 C7 H7A 109.5 . . ? S1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? S1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? S1 C8 H8A 109.5 . . ? S1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 N1 C3 123.02(13) . . ? C1 N1 H1N 118.3(11) . . ? C3 N1 H1N 117.1(11) . . ? C2 O3 C6 115.88(12) . . ? O4 S1 C8 106.15(8) . . ? O4 S1 C7 105.81(7) . . ? C8 S1 C7 97.51(9) . . ? 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 O1 C1 C2 O2 -160.79(15) . . . . ? N1 C1 C2 O2 19.3(2) . . . . ? O1 C1 C2 O3 18.11(19) . . . . ? N1 C1 C2 O3 -161.83(12) . . . . ? C3 C3 C4 C5 -2.3(2) 2_554 . . . ? N1 C3 C4 C5 176.27(14) . . . . ? C3 C4 C5 C5 0.1(3) . . . 2_554 ? O1 C1 N1 C3 -9.2(2) . . . . ? C2 C1 N1 C3 170.77(13) . . . . ? C4 C3 N1 C1 51.9(2) . . . . ? C3 C3 N1 C1 -129.48(18) 2_554 . . . ? O2 C2 O3 C6 -3.0(2) . . . . ? C1 C2 O3 C6 178.13(12) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.236 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.046 data_abducuni _database_code_depnum_ccdc_archive 'CCDC 888734' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H4 N2 Ni O6, 2(C16 H36 N)' _chemical_formula_sum 'C42 H76 N4 Ni O6' _chemical_formula_weight 791.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.5088(4) _cell_length_b 17.1731(4) _cell_length_c 14.2230(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.997(3) _cell_angle_gamma 90.00 _cell_volume 4518.08(19) _cell_formula_units_Z 4 _cell_measurement_temperature 115 _cell_measurement_reflns_used 4953 _cell_measurement_theta_min 3.5091 _cell_measurement_theta_max 62.6260 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.983 _exptl_absorpt_correction_T_min 0.76880 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET) (compiled Mar 22 2010,13:57:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 115 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'oxford gemini s' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 5 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7198 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 62.71 _reflns_number_total 3542 _reflns_number_gt 3021 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET) (compiled Mar 22 2010,13:57:49) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET) (compiled Mar 22 2010,13:57:49) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET) (compiled Mar 22 2010,13:57:49) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0807P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3542 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.88229(9) -0.14588(10) 0.65458(10) 0.0280(4) Uani 1 1 d . . . C2 C 0.87699(9) -0.05568(10) 0.65468(10) 0.0299(4) Uani 1 1 d . . . C3 C 0.96805(9) -0.24327(10) 0.72077(11) 0.0281(4) Uani 1 1 d . . . C4 C 0.93876(9) -0.31339(10) 0.68929(12) 0.0339(4) Uani 1 1 d . . . H4 H 0.8984 -0.3139 0.6485 0.041 Uiso 1 1 calc R . . C5 C 0.97048(10) -0.38302(11) 0.71948(13) 0.0407(4) Uani 1 1 d . . . H5 H 0.9514 -0.4301 0.6980 0.049 Uiso 1 1 calc R . . C6 C 0.91672(8) -0.14423(9) 0.34264(11) 0.0271(4) Uani 1 1 d . . . H6A H 0.9436 -0.1825 0.3079 0.033 Uiso 1 1 calc R . . H6B H 0.9215 -0.0947 0.3107 0.033 Uiso 1 1 calc R . . C7 C 0.95138(8) -0.13691(9) 0.44006(11) 0.0274(4) Uani 1 1 d . . . H7A H 0.9385 -0.1814 0.4780 0.033 Uiso 1 1 calc R . . H7B H 0.9341 -0.0902 0.4703 0.033 Uiso 1 1 calc R . . C8 C 1.03352(9) -0.13300(11) 0.43195(12) 0.0319(4) Uani 1 1 d . . . H8A H 1.0513 -0.1842 0.4154 0.038 Uiso 1 1 calc R . . H8B H 1.0449 -0.0975 0.3815 0.038 Uiso 1 1 calc R . . C9 C 1.07210(10) -0.10625(11) 0.52172(13) 0.0389(4) Uani 1 1 d . . . H9A H 1.1233 -0.1055 0.5129 0.058 Uiso 1 1 calc R . . H9B H 1.0615 -0.1414 0.5718 0.058 Uiso 1 1 calc R . . H9C H 1.0560 -0.0549 0.5374 0.058 Uiso 1 1 calc R . . C10 C 0.79171(8) -0.10802(10) 0.38885(11) 0.0265(4) Uani 1 1 d . . . H10A H 0.7423 -0.1267 0.3889 0.032 Uiso 1 1 calc R . . H10B H 0.8091 -0.1046 0.4538 0.032 Uiso 1 1 calc R . . C11 C 0.79193(9) -0.02709(9) 0.34641(11) 0.0293(4) Uani 1 1 d . . . H11A H 0.7820 -0.0306 0.2791 0.035 Uiso 1 1 calc R . . H11B H 0.8393 -0.0038 0.3565 0.035 Uiso 1 1 calc R . . C12 C 0.73528(10) 0.02411(10) 0.39058(12) 0.0366(4) Uani 1 1 d . . . H12A H 0.7451 0.0273 0.4579 0.044 Uiso 1 1 calc R . . H12B H 0.6879 0.0008 0.3804 0.044 Uiso 1 1 calc R . . C13 C 0.73512(12) 0.10562(11) 0.34873(14) 0.0466(5) Uani 1 1 d . . . H13A H 0.7002 0.1372 0.3794 0.070 Uiso 1 1 calc R . . H13B H 0.7228 0.1028 0.2827 0.070 Uiso 1 1 calc R . . H13C H 0.7822 0.1284 0.3577 0.070 Uiso 1 1 calc R . . C14 C 0.81563(9) -0.17179(10) 0.23427(10) 0.0273(4) Uani 1 1 d . . . H14A H 0.8322 -0.1247 0.2040 0.033 Uiso 1 1 calc R . . H14B H 0.8410 -0.2152 0.2070 0.033 Uiso 1 1 calc R . . C15 C 0.73571(9) -0.18127(10) 0.21065(11) 0.0291(4) Uani 1 1 d . . . H15A H 0.7089 -0.1397 0.2397 0.035 Uiso 1 1 calc R . . H15B H 0.7189 -0.2305 0.2352 0.035 Uiso 1 1 calc R . . C16 C 0.72261(10) -0.17897(11) 0.10418(11) 0.0350(4) Uani 1 1 d . . . H16A H 0.7390 -0.1293 0.0804 0.042 Uiso 1 1 calc R . . H16B H 0.7509 -0.2196 0.0756 0.042 Uiso 1 1 calc R . . C17 C 0.64360(10) -0.19001(12) 0.07572(12) 0.0414(4) Uani 1 1 d . . . H17A H 0.6378 -0.1875 0.0084 0.062 Uiso 1 1 calc R . . H17B H 0.6154 -0.1496 0.1034 0.062 Uiso 1 1 calc R . . H17C H 0.6275 -0.2398 0.0973 0.062 Uiso 1 1 calc R . . C18 C 0.82536(8) -0.24495(9) 0.38738(11) 0.0272(4) Uani 1 1 d . . . H18A H 0.8294 -0.2363 0.4548 0.033 Uiso 1 1 calc R . . H18B H 0.7762 -0.2617 0.3727 0.033 Uiso 1 1 calc R . . C19 C 0.87586(10) -0.31074(10) 0.36308(12) 0.0330(4) Uani 1 1 d . . . H19A H 0.9252 -0.2967 0.3808 0.040 Uiso 1 1 calc R . . H19B H 0.8732 -0.3201 0.2958 0.040 Uiso 1 1 calc R . . C20 C 0.85427(11) -0.38468(11) 0.41557(13) 0.0406(4) Uani 1 1 d . . . H20A H 0.8585 -0.3752 0.4828 0.049 Uiso 1 1 calc R . . H20B H 0.8041 -0.3966 0.3999 0.049 Uiso 1 1 calc R . . C21 C 0.90073(16) -0.45419(14) 0.3914(2) 0.0771(8) Uani 1 1 d . . . H21A H 0.8854 -0.4989 0.4260 0.116 Uiso 1 1 calc R . . H21B H 0.9504 -0.4430 0.4078 0.116 Uiso 1 1 calc R . . H21C H 0.8958 -0.4646 0.3252 0.116 Uiso 1 1 calc R . . N1 N 0.94212(7) -0.16766(8) 0.70226(8) 0.0275(3) Uani 1 1 d . . . N2 N 0.83743(7) -0.16731(8) 0.33828(8) 0.0248(3) Uani 1 1 d . . . O1 O 0.83589(6) -0.18753(7) 0.61376(8) 0.0336(3) Uani 1 1 d . . . O3 O 0.82510(7) -0.02317(7) 0.61479(8) 0.0388(3) Uani 1 1 d . . . O2 O 0.92934(7) -0.02002(6) 0.69934(7) 0.0325(3) Uani 1 1 d . . . Ni1 Ni 1.0000 -0.08943(2) 0.7500 0.02489(15) Uani 1 2 d S . . 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 C1 0.0297(8) 0.0352(9) 0.0196(8) -0.0001(7) 0.0070(6) -0.0004(7) C2 0.0334(9) 0.0358(9) 0.0210(8) 0.0016(7) 0.0054(7) 0.0023(8) C3 0.0312(8) 0.0274(8) 0.0263(8) 0.0002(7) 0.0095(6) 0.0003(7) C4 0.0347(9) 0.0319(9) 0.0357(9) -0.0051(7) 0.0090(7) -0.0044(7) C5 0.0432(10) 0.0287(9) 0.0512(11) -0.0058(8) 0.0144(8) -0.0044(8) C6 0.0264(8) 0.0271(8) 0.0283(8) -0.0007(7) 0.0086(6) -0.0019(7) C7 0.0298(8) 0.0256(8) 0.0272(8) -0.0011(7) 0.0068(6) -0.0014(7) C8 0.0303(8) 0.0339(9) 0.0320(9) 0.0017(7) 0.0067(7) -0.0021(7) C9 0.0326(9) 0.0447(11) 0.0394(10) -0.0006(8) 0.0008(8) -0.0036(8) C10 0.0281(8) 0.0293(9) 0.0225(8) -0.0048(6) 0.0054(6) 0.0013(7) C11 0.0329(8) 0.0290(9) 0.0261(8) -0.0029(7) 0.0019(6) -0.0007(7) C12 0.0425(10) 0.0348(10) 0.0326(9) -0.0035(7) 0.0024(7) 0.0081(8) C13 0.0616(13) 0.0369(10) 0.0409(11) -0.0012(8) -0.0012(9) 0.0154(9) C14 0.0338(9) 0.0288(9) 0.0195(8) -0.0024(6) 0.0062(6) -0.0009(7) C15 0.0346(9) 0.0286(8) 0.0244(8) -0.0024(7) 0.0045(6) -0.0038(7) C16 0.0415(10) 0.0394(10) 0.0243(8) -0.0010(7) 0.0033(7) -0.0009(8) C17 0.0455(11) 0.0479(11) 0.0306(9) -0.0034(8) -0.0015(8) -0.0043(9) C18 0.0319(8) 0.0252(8) 0.0247(8) 0.0012(6) 0.0047(6) -0.0035(7) C19 0.0387(9) 0.0282(9) 0.0325(9) -0.0019(7) 0.0064(7) -0.0005(7) C20 0.0538(11) 0.0284(9) 0.0400(10) 0.0037(8) 0.0072(8) -0.0005(8) C21 0.104(2) 0.0341(12) 0.096(2) 0.0120(12) 0.0352(16) 0.0139(13) N1 0.0299(7) 0.0282(7) 0.0246(7) -0.0002(6) 0.0044(6) 0.0004(6) N2 0.0278(7) 0.0250(7) 0.0218(6) -0.0009(5) 0.0051(5) -0.0017(5) O1 0.0303(6) 0.0418(7) 0.0289(6) -0.0017(5) 0.0024(5) -0.0064(5) O3 0.0393(7) 0.0442(7) 0.0327(6) 0.0042(5) -0.0015(5) 0.0093(6) O2 0.0381(6) 0.0293(6) 0.0302(6) 0.0005(5) 0.0012(5) 0.0010(5) Ni1 0.0282(2) 0.0237(2) 0.0229(2) 0.000 0.00224(15) 0.000 _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 C1 O1 1.246(2) . ? C1 N1 1.332(2) . ? C1 C2 1.552(2) . ? C2 O3 1.232(2) . ? C2 O2 1.294(2) . ? C3 C4 1.388(2) . ? C3 N1 1.406(2) . ? C3 C3 1.422(3) 2_756 ? C4 C5 1.393(3) . ? C4 H4 0.9300 . ? C5 C5 1.372(4) 2_756 ? C5 H5 0.9300 . ? C6 C7 1.512(2) . ? C6 N2 1.519(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.530(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.512(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.515(2) . ? C10 N2 1.521(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.521(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.521(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.514(2) . ? C14 N2 1.5216(19) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.526(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.516(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.514(2) . ? C18 N2 1.525(2) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.533(2) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.518(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? N1 Ni1 1.8338(13) . ? O2 Ni1 1.8933(12) . ? Ni1 N1 1.8338(13) 2_756 ? Ni1 O2 1.8933(12) 2_756 ? 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 O1 C1 N1 128.58(16) . . ? O1 C1 C2 122.07(14) . . ? N1 C1 C2 109.35(14) . . ? O3 C2 O2 124.74(16) . . ? O3 C2 C1 120.02(15) . . ? O2 C2 C1 115.24(14) . . ? C4 C3 N1 127.86(15) . . ? C4 C3 C3 119.74(10) . 2_756 ? N1 C3 C3 112.40(9) . 2_756 ? C3 C4 C5 119.30(17) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C5 C5 C4 120.85(11) 2_756 . ? C5 C5 H5 119.6 2_756 . ? C4 C5 H5 119.6 . . ? C7 C6 N2 115.95(12) . . ? C7 C6 H6A 108.3 . . ? N2 C6 H6A 108.3 . . ? C7 C6 H6B 108.3 . . ? N2 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C6 C7 C8 109.00(12) . . ? C6 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? C6 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C9 C8 C7 113.00(14) . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 N2 114.61(12) . . ? C11 C10 H10A 108.6 . . ? N2 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? N2 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 110.75(14) . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C13 111.25(15) . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 N2 116.42(12) . . ? C15 C14 H14A 108.2 . . ? N2 C14 H14A 108.2 . . ? C15 C14 H14B 108.2 . . ? N2 C14 H14B 108.2 . . ? H14A C14 H14B 107.3 . . ? C14 C15 C16 109.74(13) . . ? C14 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? C14 C15 H15B 109.7 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C17 C16 C15 112.36(15) . . ? C17 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? C17 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.9 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 N2 116.51(13) . . ? C19 C18 H18A 108.2 . . ? N2 C18 H18A 108.2 . . ? C19 C18 H18B 108.2 . . ? N2 C18 H18B 108.2 . . ? H18A C18 H18B 107.3 . . ? C18 C19 C20 109.48(14) . . ? C18 C19 H19A 109.8 . . ? C20 C19 H19A 109.8 . . ? C18 C19 H19B 109.8 . . ? C20 C19 H19B 109.8 . . ? H19A C19 H19B 108.2 . . ? C21 C20 C19 112.46(17) . . ? C21 C20 H20A 109.1 . . ? C19 C20 H20A 109.1 . . ? C21 C20 H20B 109.1 . . ? C19 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C1 N1 C3 128.83(14) . . ? C1 N1 Ni1 116.58(11) . . ? C3 N1 Ni1 114.59(10) . . ? C6 N2 C10 111.01(12) . . ? C6 N2 C14 106.01(11) . . ? C10 N2 C14 111.14(12) . . ? C6 N2 C18 111.47(12) . . ? C10 N2 C18 106.02(11) . . ? C14 N2 C18 111.28(12) . . ? C2 O2 Ni1 112.61(11) . . ? N1 Ni1 N1 85.79(8) . 2_756 ? N1 Ni1 O2 86.18(5) . . ? N1 Ni1 O2 171.49(6) 2_756 . ? N1 Ni1 O2 171.49(6) . 2_756 ? N1 Ni1 O2 86.18(5) 2_756 2_756 ? O2 Ni1 O2 101.97(7) . 2_756 ? 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 O1 C1 C2 O3 1.2(2) . . . . ? N1 C1 C2 O3 -179.48(14) . . . . ? O1 C1 C2 O2 -179.51(13) . . . . ? N1 C1 C2 O2 -0.16(18) . . . . ? N1 C3 C4 C5 -176.67(15) . . . . ? C3 C3 C4 C5 3.2(3) 2_756 . . . ? C3 C4 C5 C5 0.8(3) . . . 2_756 ? N2 C6 C7 C8 166.51(13) . . . . ? C6 C7 C8 C9 166.02(14) . . . . ? N2 C10 C11 C12 170.26(13) . . . . ? C10 C11 C12 C13 179.84(15) . . . . ? N2 C14 C15 C16 176.02(13) . . . . ? C14 C15 C16 C17 178.71(15) . . . . ? N2 C18 C19 C20 -177.86(14) . . . . ? C18 C19 C20 C21 177.62(18) . . . . ? O1 C1 N1 C3 -1.4(3) . . . . ? C2 C1 N1 C3 179.30(14) . . . . ? O1 C1 N1 Ni1 177.91(13) . . . . ? C2 C1 N1 Ni1 -1.38(15) . . . . ? C4 C3 N1 C1 3.5(3) . . . . ? C3 C3 N1 C1 -176.37(15) 2_756 . . . ? C4 C3 N1 Ni1 -175.79(13) . . . . ? C3 C3 N1 Ni1 4.3(2) 2_756 . . . ? C7 C6 N2 C10 59.91(17) . . . . ? C7 C6 N2 C14 -179.28(13) . . . . ? C7 C6 N2 C18 -58.04(17) . . . . ? C11 C10 N2 C6 62.77(16) . . . . ? C11 C10 N2 C14 -54.96(17) . . . . ? C11 C10 N2 C18 -176.02(12) . . . . ? C15 C14 N2 C6 -170.55(14) . . . . ? C15 C14 N2 C10 -49.83(18) . . . . ? C15 C14 N2 C18 68.09(17) . . . . ? C19 C18 N2 C6 -47.51(17) . . . . ? C19 C18 N2 C10 -168.43(13) . . . . ? C19 C18 N2 C14 70.61(17) . . . . ? O3 C2 O2 Ni1 -179.18(13) . . . . ? C1 C2 O2 Ni1 1.53(16) . . . . ? C1 N1 Ni1 N1 179.01(14) . . . 2_756 ? C3 N1 Ni1 N1 -1.57(7) . . . 2_756 ? C1 N1 Ni1 O2 1.84(11) . . . . ? C3 N1 Ni1 O2 -178.75(11) . . . . ? C1 N1 Ni1 O2 -161.6(3) . . . 2_756 ? C3 N1 Ni1 O2 17.8(4) . . . 2_756 ? C2 O2 Ni1 N1 -1.85(11) . . . . ? C2 O2 Ni1 N1 -21.2(4) . . . 2_756 ? C2 O2 Ni1 O2 175.68(12) . . . 2_756 ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 62.71 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.407 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.052 data_cuopba _database_code_depnum_ccdc_archive 'CCDC 888735' #TrackingRef '7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H4 Cu N2 O6, 2(C16 H36 N)' _chemical_formula_sum 'C42 H76 Cu N4 O6' _chemical_formula_weight 796.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.5716(9) _cell_length_b 17.2023(7) _cell_length_c 14.1556(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.897(4) _cell_angle_gamma 90.00 _cell_volume 4519.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 115 _cell_measurement_reflns_used 4076 _cell_measurement_theta_min 4.6393 _cell_measurement_theta_max 62.6711 _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1732 _exptl_absorpt_coefficient_mu 1.045 _exptl_absorpt_correction_T_min 0.7176 _exptl_absorpt_correction_T_max 0.9594 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET) (compiled Mar 22 2010,13:57:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 115 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'oxford gemini s' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6968 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.64 _diffrn_reflns_theta_max 62.76 _reflns_number_total 3440 _reflns_number_gt 2596 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET) (compiled Mar 22 2010,13:57:49) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET) (compiled Mar 22 2010,13:57:49) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET) (compiled Mar 22 2010,13:57:49) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0952P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3440 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1300 _refine_ls_wR_factor_gt 0.1246 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.943 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.38063(15) -0.14641(16) 1.15524(16) 0.0345(6) Uani 1 1 d . . . C2 C 0.37344(16) -0.05615(17) 1.15548(16) 0.0374(6) Uani 1 1 d . . . C3 C 0.46784(15) -0.24219(15) 1.22082(17) 0.0348(6) Uani 1 1 d . . . C4 C 0.43898(16) -0.31262(16) 1.18984(18) 0.0396(7) Uani 1 1 d . . . H4 H 0.3987 -0.3132 1.1490 0.048 Uiso 1 1 calc R . . C5 C 0.47025(18) -0.38210(17) 1.2198(2) 0.0474(7) Uani 1 1 d . . . H5 H 0.4508 -0.4291 1.1987 0.057 Uiso 1 1 calc R . . C6 C 0.41570(15) -0.14448(15) 0.84371(17) 0.0341(6) Uani 1 1 d . . . H6A H 0.4198 -0.0947 0.8120 0.041 Uiso 1 1 calc R . . H6B H 0.4430 -0.1820 0.8084 0.041 Uiso 1 1 calc R . . C7 C 0.45064(15) -0.13717(15) 0.94241(17) 0.0337(6) Uani 1 1 d . . . H7A H 0.4322 -0.0915 0.9737 0.040 Uiso 1 1 calc R . . H7B H 0.4391 -0.1824 0.9798 0.040 Uiso 1 1 calc R . . C8 C 0.53173(16) -0.13053(17) 0.93453(18) 0.0395(6) Uani 1 1 d . . . H8A H 0.5421 -0.0938 0.8848 0.047 Uiso 1 1 calc R . . H8B H 0.5508 -0.1807 0.9165 0.047 Uiso 1 1 calc R . . C9 C 0.56999(17) -0.10420(18) 1.02572(19) 0.0451(7) Uani 1 1 d . . . H9A H 0.6209 -0.1013 1.0164 0.068 Uiso 1 1 calc R . . H9B H 0.5608 -0.1408 1.0751 0.068 Uiso 1 1 calc R . . H9C H 0.5524 -0.0539 1.0432 0.068 Uiso 1 1 calc R . . C10 C 0.32642(15) -0.24657(14) 0.88796(16) 0.0335(6) Uani 1 1 d . . . H10A H 0.3301 -0.2383 0.9557 0.040 Uiso 1 1 calc R . . H10B H 0.2777 -0.2640 0.8728 0.040 Uiso 1 1 calc R . . C11 C 0.37785(16) -0.31112(15) 0.86311(18) 0.0386(6) Uani 1 1 d . . . H11A H 0.4268 -0.2962 0.8810 0.046 Uiso 1 1 calc R . . H11B H 0.3754 -0.3202 0.7954 0.046 Uiso 1 1 calc R . . C12 C 0.35747(19) -0.38553(17) 0.9154(2) 0.0479(7) Uani 1 1 d . . . H12A H 0.3610 -0.3761 0.9829 0.057 Uiso 1 1 calc R . . H12B H 0.3078 -0.3986 0.8991 0.057 Uiso 1 1 calc R . . C13 C 0.4053(3) -0.4537(2) 0.8915(3) 0.0830(13) Uani 1 1 d . . . H13A H 0.3906 -0.4987 0.9260 0.124 Uiso 1 1 calc R . . H13B H 0.4544 -0.4414 0.9085 0.124 Uiso 1 1 calc R . . H13C H 0.4010 -0.4641 0.8249 0.124 Uiso 1 1 calc R . . C14 C 0.31617(15) -0.17276(15) 0.73463(16) 0.0341(6) Uani 1 1 d . . . H14A H 0.3323 -0.1255 0.7046 0.041 Uiso 1 1 calc R . . H14B H 0.3419 -0.2157 0.7069 0.041 Uiso 1 1 calc R . . C15 C 0.23669(15) -0.18295(15) 0.71080(16) 0.0357(6) Uani 1 1 d . . . H15A H 0.2096 -0.1417 0.7400 0.043 Uiso 1 1 calc R . . H15B H 0.2203 -0.2322 0.7356 0.043 Uiso 1 1 calc R . . C16 C 0.22333(17) -0.18094(18) 0.60392(18) 0.0432(7) Uani 1 1 d . . . H16A H 0.2396 -0.1314 0.5798 0.052 Uiso 1 1 calc R . . H16B H 0.2516 -0.2215 0.5752 0.052 Uiso 1 1 calc R . . C17 C 0.14490(17) -0.19212(19) 0.57525(19) 0.0483(8) Uani 1 1 d . . . H17A H 0.1394 -0.1904 0.5076 0.072 Uiso 1 1 calc R . . H17B H 0.1167 -0.1515 0.6022 0.072 Uiso 1 1 calc R . . H17C H 0.1287 -0.2416 0.5977 0.072 Uiso 1 1 calc R . . C18 C 0.29081(15) -0.11039(15) 0.89008(16) 0.0325(6) Uani 1 1 d . . . H18A H 0.2418 -0.1299 0.8892 0.039 Uiso 1 1 calc R . . H18B H 0.3075 -0.1073 0.9556 0.039 Uiso 1 1 calc R . . C19 C 0.29022(15) -0.02930(15) 0.84848(17) 0.0355(6) Uani 1 1 d . . . H19A H 0.2815 -0.0324 0.7807 0.043 Uiso 1 1 calc R . . H19B H 0.3370 -0.0053 0.8599 0.043 Uiso 1 1 calc R . . C20 C 0.23234(17) 0.02065(17) 0.89175(18) 0.0432(7) Uani 1 1 d . . . H20A H 0.1856 -0.0032 0.8801 0.052 Uiso 1 1 calc R . . H20B H 0.2410 0.0237 0.9596 0.052 Uiso 1 1 calc R . . C21 C 0.2322(2) 0.10205(18) 0.8500(2) 0.0531(8) Uani 1 1 d . . . H21A H 0.1954 0.1325 0.8783 0.080 Uiso 1 1 calc R . . H21B H 0.2228 0.0991 0.7830 0.080 Uiso 1 1 calc R . . H21C H 0.2783 0.1259 0.8623 0.080 Uiso 1 1 calc R . . N1 N 0.44058(12) -0.16804(12) 1.20153(13) 0.0346(5) Uani 1 1 d . . . N2 N 0.33780(12) -0.16862(12) 0.83914(13) 0.0312(5) Uani 1 1 d . . . O1 O 0.33429(10) -0.18800(11) 1.11507(12) 0.0400(5) Uani 1 1 d . . . O2 O 0.42416(11) -0.01797(10) 1.20003(11) 0.0385(4) Uani 1 1 d . . . O3 O 0.32072(11) -0.02600(12) 1.11463(12) 0.0456(5) Uani 1 1 d . . . Cu1 Cu 0.5000 -0.08567(3) 1.2500 0.0344(2) Uani 1 2 d S . . 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 C1 0.0421(17) 0.0398(15) 0.0223(12) 0.0024(10) 0.0106(11) 0.0002(12) C2 0.0445(17) 0.0430(15) 0.0253(12) 0.0002(11) 0.0084(12) 0.0015(13) C3 0.0425(17) 0.0323(14) 0.0301(13) 0.0015(10) 0.0098(10) 0.0010(12) C4 0.0471(19) 0.0344(15) 0.0380(14) -0.0041(10) 0.0097(12) -0.0044(12) C5 0.058(2) 0.0333(15) 0.0519(17) -0.0055(12) 0.0147(12) -0.0053(14) C6 0.0378(17) 0.0328(14) 0.0324(13) 0.0004(10) 0.0091(11) -0.0004(11) C7 0.0396(16) 0.0297(13) 0.0321(13) -0.0011(10) 0.0068(10) -0.0014(11) C8 0.0419(17) 0.0409(15) 0.0360(14) 0.0020(11) 0.0070(11) -0.0026(12) C9 0.0430(18) 0.0491(17) 0.0432(15) -0.0006(12) 0.0029(12) -0.0055(13) C10 0.0429(16) 0.0300(13) 0.0279(12) 0.0011(9) 0.0065(10) -0.0053(11) C11 0.0460(17) 0.0331(15) 0.0370(14) -0.0005(10) 0.0075(11) 0.0005(12) C12 0.066(2) 0.0330(15) 0.0451(16) 0.0006(11) 0.0078(14) -0.0012(14) C13 0.116(4) 0.037(2) 0.098(3) 0.0091(18) 0.033(2) 0.018(2) C14 0.0479(18) 0.0329(14) 0.0218(12) -0.0033(9) 0.0071(10) -0.0010(12) C15 0.0464(17) 0.0336(14) 0.0276(12) -0.0031(10) 0.0076(11) -0.0046(12) C16 0.055(2) 0.0451(16) 0.0296(14) -0.0011(11) 0.0060(12) -0.0005(13) C17 0.057(2) 0.0541(19) 0.0334(14) -0.0030(12) 0.0002(13) -0.0076(15) C18 0.0384(16) 0.0333(14) 0.0262(12) -0.0039(9) 0.0064(10) 0.0007(11) C19 0.0410(16) 0.0335(14) 0.0319(13) -0.0026(10) 0.0018(10) -0.0017(11) C20 0.0538(19) 0.0421(16) 0.0339(14) -0.0036(11) 0.0046(12) 0.0086(14) C21 0.074(2) 0.0427(17) 0.0425(16) 0.0001(12) 0.0022(14) 0.0177(15) N1 0.0410(15) 0.0340(12) 0.0291(11) -0.0001(8) 0.0046(9) 0.0006(10) N2 0.0380(13) 0.0299(11) 0.0258(10) -0.0014(8) 0.0053(8) 0.0000(9) O1 0.0402(12) 0.0476(11) 0.0324(9) -0.0016(8) 0.0033(8) -0.0080(9) O2 0.0480(12) 0.0337(10) 0.0341(9) -0.0007(7) 0.0057(8) 0.0014(9) O3 0.0479(13) 0.0502(12) 0.0386(10) 0.0032(8) -0.0002(8) 0.0120(10) Cu1 0.0427(4) 0.0316(3) 0.0290(3) 0.000 0.0037(2) 0.000 _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 C1 O1 1.242(3) . ? C1 N1 1.326(4) . ? C1 C2 1.558(4) . ? C2 O3 1.235(3) . ? C2 O2 1.295(3) . ? C3 C4 1.390(4) . ? C3 N1 1.396(3) . ? C3 C3 1.430(6) 2_657 ? C4 C5 1.389(4) . ? C4 H4 0.9300 . ? C5 C5 1.375(7) 2_657 ? C5 H5 0.9300 . ? C6 N2 1.505(4) . ? C6 C7 1.526(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.518(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.522(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.514(4) . ? C10 N2 1.526(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.532(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.515(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.513(4) . ? C14 N2 1.522(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.526(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.511(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.514(4) . ? C18 N2 1.525(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.521(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.520(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? N1 Cu1 1.910(2) . ? O2 Cu1 1.9428(19) . ? Cu1 N1 1.910(2) 2_657 ? Cu1 O2 1.9428(19) 2_657 ? 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 O1 C1 N1 128.5(3) . . ? O1 C1 C2 121.1(2) . . ? N1 C1 C2 110.4(2) . . ? O3 C2 O2 124.6(3) . . ? O3 C2 C1 119.0(3) . . ? O2 C2 C1 116.5(2) . . ? C4 C3 N1 127.0(3) . . ? C4 C3 C3 119.23(17) . 2_657 ? N1 C3 C3 113.81(15) . 2_657 ? C5 C4 C3 120.1(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C5 C4 120.61(18) 2_657 . ? C5 C5 H5 119.7 2_657 . ? C4 C5 H5 119.7 . . ? N2 C6 C7 116.18(19) . . ? N2 C6 H6A 108.2 . . ? C7 C6 H6A 108.2 . . ? N2 C6 H6B 108.2 . . ? C7 C6 H6B 108.2 . . ? H6A C6 H6B 107.4 . . ? C8 C7 C6 109.4(2) . . ? C8 C7 H7A 109.8 . . ? C6 C7 H7A 109.8 . . ? C8 C7 H7B 109.8 . . ? C6 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? C7 C8 C9 113.4(2) . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 N2 116.2(2) . . ? C11 C10 H10A 108.2 . . ? N2 C10 H10A 108.2 . . ? C11 C10 H10B 108.2 . . ? N2 C10 H10B 108.2 . . ? H10A C10 H10B 107.4 . . ? C10 C11 C12 109.4(2) . . ? C10 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? C10 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? C13 C12 C11 112.5(3) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 N2 116.50(19) . . ? C15 C14 H14A 108.2 . . ? N2 C14 H14A 108.2 . . ? C15 C14 H14B 108.2 . . ? N2 C14 H14B 108.2 . . ? H14A C14 H14B 107.3 . . ? C14 C15 C16 110.1(2) . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.2 . . ? C17 C16 C15 112.8(2) . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16B 109.0 . . ? C15 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 N2 114.71(19) . . ? C19 C18 H18A 108.6 . . ? N2 C18 H18A 108.6 . . ? C19 C18 H18B 108.6 . . ? N2 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C18 C19 C20 111.1(2) . . ? C18 C19 H19A 109.4 . . ? C20 C19 H19A 109.4 . . ? C18 C19 H19B 109.4 . . ? C20 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C21 C20 C19 110.9(2) . . ? C21 C20 H20A 109.5 . . ? C19 C20 H20A 109.5 . . ? C21 C20 H20B 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 108.1 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C1 N1 C3 130.2(2) . . ? C1 N1 Cu1 115.79(18) . . ? C3 N1 Cu1 113.97(18) . . ? C6 N2 C14 106.09(18) . . ? C6 N2 C18 111.27(19) . . ? C14 N2 C18 110.71(19) . . ? C6 N2 C10 111.7(2) . . ? C14 N2 C10 111.29(18) . . ? C18 N2 C10 105.84(18) . . ? C2 O2 Cu1 112.34(17) . . ? N1 Cu1 N1 84.19(13) 2_657 . ? N1 Cu1 O2 84.87(9) 2_657 2_657 ? N1 Cu1 O2 168.24(9) . 2_657 ? N1 Cu1 O2 168.24(9) 2_657 . ? N1 Cu1 O2 84.87(9) . . ? O2 Cu1 O2 106.34(11) 2_657 . ? 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 O1 C1 C2 O3 -0.2(3) . . . . ? N1 C1 C2 O3 179.4(2) . . . . ? O1 C1 C2 O2 179.3(2) . . . . ? N1 C1 C2 O2 -1.0(3) . . . . ? N1 C3 C4 C5 -176.2(2) . . . . ? C3 C3 C4 C5 3.5(4) 2_657 . . . ? C3 C4 C5 C5 0.1(5) . . . 2_657 ? N2 C6 C7 C8 167.4(2) . . . . ? C6 C7 C8 C9 166.5(2) . . . . ? N2 C10 C11 C12 -178.1(2) . . . . ? C10 C11 C12 C13 178.2(3) . . . . ? N2 C14 C15 C16 176.5(2) . . . . ? C14 C15 C16 C17 179.1(2) . . . . ? N2 C18 C19 C20 169.8(2) . . . . ? C18 C19 C20 C21 179.8(2) . . . . ? O1 C1 N1 C3 -2.0(4) . . . . ? C2 C1 N1 C3 178.4(2) . . . . ? O1 C1 N1 Cu1 177.9(2) . . . . ? C2 C1 N1 Cu1 -1.7(2) . . . . ? C4 C3 N1 C1 4.1(4) . . . . ? C3 C3 N1 C1 -175.6(2) 2_657 . . . ? C4 C3 N1 Cu1 -175.8(2) . . . . ? C3 C3 N1 Cu1 4.5(3) 2_657 . . . ? C7 C6 N2 C14 -179.2(2) . . . . ? C7 C6 N2 C18 60.3(3) . . . . ? C7 C6 N2 C10 -57.8(3) . . . . ? C15 C14 N2 C6 -170.2(2) . . . . ? C15 C14 N2 C18 -49.3(3) . . . . ? C15 C14 N2 C10 68.1(3) . . . . ? C19 C18 N2 C6 62.2(3) . . . . ? C19 C18 N2 C14 -55.5(3) . . . . ? C19 C18 N2 C10 -176.2(2) . . . . ? C11 C10 N2 C6 -47.4(3) . . . . ? C11 C10 N2 C14 71.0(3) . . . . ? C11 C10 N2 C18 -168.7(2) . . . . ? O3 C2 O2 Cu1 -177.34(19) . . . . ? C1 C2 O2 Cu1 3.1(3) . . . . ? C1 N1 Cu1 N1 178.5(2) . . . 2_657 ? C3 N1 Cu1 N1 -1.62(12) . . . 2_657 ? C1 N1 Cu1 O2 -160.0(3) . . . 2_657 ? C3 N1 Cu1 O2 19.9(5) . . . 2_657 ? C1 N1 Cu1 O2 2.77(17) . . . . ? C3 N1 Cu1 O2 -177.32(17) . . . . ? C2 O2 Cu1 N1 -24.7(4) . . . 2_657 ? C2 O2 Cu1 N1 -3.24(16) . . . . ? C2 O2 Cu1 O2 173.16(18) . . . 2_657 ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 62.76 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.594 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.063