# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Delgado, Rita' _publ_contact_author_email delgado@itqb.unl.pt _publ_section_title ; Dimetallic complexes of macrocycles with two rigid dibenzofuran units as receptors for detection of anionic substrates ; loop_ _publ_author_name R.Delgado F.Li S.Carvalho M.Drew V.Felix # Attachment '- DT-ART-04-2010-000340_cif.cif' data_compound_cu _database_code_depnum_ccdc_archive 'CCDC 774558' #TrackingRef '- DT-ART-04-2010-000340_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C53 H54 Cu2 N6 O11' _chemical_formula_weight 1078.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 12.9418(14) _cell_length_b 12.9883(12) _cell_length_c 15.6222(14) _cell_angle_alpha 90.00 _cell_angle_beta 112.356(9) _cell_angle_gamma 90.00 _cell_volume 2428.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16327 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 30.00 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.945 _exptl_absorpt_correction_type Empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; 'The systematic absences were only consistent with space group P21c' 'ABSPACK, Oxford Diffraction Ltd' ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device_type 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 16327 _diffrn_reflns_av_R_equivalents 0.0966 _diffrn_reflns_av_sigmaI/netI 0.1578 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 30.00 _reflns_number_total 7002 _reflns_number_gt 3861 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0822P)^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 7002 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1861 _refine_ls_R_factor_gt 0.0978 _refine_ls_wR_factor_ref 0.2072 _refine_ls_wR_factor_gt 0.1788 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.45973(5) 0.35717(5) 0.60988(4) 0.02183(18) Uani 1 d . . . N1 N 0.5040(4) 0.3193(3) 0.7429(3) 0.0264(10) Uani 1 d . . . H1 H 0.4663 0.2594 0.7461 0.032 Uiso 1 calc R . . C2 C 0.4661(4) 0.4023(4) 0.7871(3) 0.0267(12) Uani 1 d . . . H2A H 0.5164 0.4625 0.7978 0.032 Uiso 1 calc R . . H2B H 0.4663 0.3789 0.8475 0.032 Uiso 1 calc R . . C3 C 0.3490(4) 0.4312(4) 0.7232(3) 0.0264(12) Uani 1 d . . . H3A H 0.2972 0.3734 0.7181 0.032 Uiso 1 calc R . . H3B H 0.3232 0.4918 0.7480 0.032 Uiso 1 calc R . . N4 N 0.3503(3) 0.4553(3) 0.6318(3) 0.0209(9) Uani 1 d . . . H4 H 0.3822 0.5203 0.6373 0.025 Uiso 1 calc R . . C5 C 0.2377(4) 0.4639(4) 0.5574(4) 0.0273(12) Uani 1 d . . . H5A H 0.1970 0.3986 0.5544 0.033 Uiso 1 calc R . . H5B H 0.2463 0.4726 0.4975 0.033 Uiso 1 calc R . . C6 C 0.1679(4) 0.5517(4) 0.5695(4) 0.0270(12) Uani 1 d . . . C7 C 0.0863(4) 0.5408(5) 0.6066(4) 0.0339(13) Uani 1 d . . . H7 H 0.0746 0.4749 0.6278 0.041 Uiso 1 calc R . . C8 C 0.0217(5) 0.6226(5) 0.6135(4) 0.0377(15) Uani 1 d . . . H8 H -0.0324 0.6115 0.6399 0.045 Uiso 1 calc R . . C9 C 0.0331(5) 0.7178(5) 0.5837(4) 0.0386(15) Uani 1 d . . . H9 H -0.0132 0.7727 0.5880 0.046 Uiso 1 calc R . . C10 C 0.1140(4) 0.7340(4) 0.5467(4) 0.0282(12) Uani 1 d . . . C11 C 0.1796(4) 0.6515(4) 0.5419(3) 0.0273(12) Uani 1 d . . . O12 O 0.2584(3) 0.6799(3) 0.5063(2) 0.0255(8) Uani 1 d . . . C13 C 0.7559(5) 0.2156(4) 0.5107(4) 0.0269(12) Uani 1 d . . . C14 C 0.1561(4) 0.8223(4) 0.5108(4) 0.0272(12) Uani 1 d . . . C15 C 0.1341(5) 0.9278(5) 0.5013(4) 0.0405(15) Uani 1 d . . . H15 H 0.0747 0.9561 0.5153 0.049 Uiso 1 calc R . . C16 C 0.8012(6) 0.0100(4) 0.5284(4) 0.0407(16) Uani 1 d . . . H16 H 0.8181 -0.0612 0.5380 0.049 Uiso 1 calc R . . C17 C 0.7105(5) 0.0501(4) 0.5448(4) 0.0343(14) Uani 1 d . . . H17 H 0.6646 0.0048 0.5626 0.041 Uiso 1 calc R . . C18 C 0.6849(5) 0.1564(4) 0.5356(4) 0.0308(13) Uani 1 d . . . C19 C 0.5804(5) 0.2011(4) 0.5414(4) 0.0287(12) Uani 1 d . . . H19A H 0.5382 0.2366 0.4823 0.034 Uiso 1 calc R . . H19B H 0.5334 0.1435 0.5473 0.034 Uiso 1 calc R . . N20 N 0.5962(3) 0.2733(3) 0.6170(3) 0.0244(10) Uani 1 d . . . H20 H 0.6482 0.3211 0.6140 0.029 Uiso 1 calc R . . C21 C 0.6459(5) 0.2267(4) 0.7100(4) 0.0332(13) Uani 1 d . . . H21A H 0.7274 0.2178 0.7275 0.040 Uiso 1 calc R . . H21B H 0.6125 0.1582 0.7099 0.040 Uiso 1 calc R . . C22 C 0.6241(5) 0.2973(5) 0.7800(4) 0.0330(14) Uani 1 d . . . H22A H 0.6465 0.2627 0.8408 0.040 Uiso 1 calc R . . H22B H 0.6673 0.3619 0.7879 0.040 Uiso 1 calc R . . C31 C 0.3029(4) 0.3557(4) 0.2837(3) 0.0250(11) Uani 1 d . . . C32 C 0.2494(5) 0.3536(5) 0.1874(4) 0.0395(14) Uani 1 d . . . H32 H 0.2821 0.3884 0.1504 0.047 Uiso 1 calc R . . C33 C 0.1507(5) 0.3023(5) 0.1456(4) 0.0423(16) Uani 1 d . . . H33 H 0.1131 0.3046 0.0802 0.051 Uiso 1 calc R . . C34 C 0.1053(5) 0.2461(5) 0.1996(4) 0.0384(15) Uani 1 d . . . H34 H 0.0358 0.2117 0.1712 0.046 Uiso 1 calc R . . C35 C 0.1616(4) 0.2410(4) 0.2936(4) 0.0310(13) Uani 1 d . . . H35 H 0.1338 0.1984 0.3294 0.037 Uiso 1 calc R . . C36 C 0.2596(4) 0.2980(4) 0.3375(3) 0.0222(11) Uani 1 d . . . C37 C 0.5895(4) 0.5814(4) 0.6768(3) 0.0259(12) Uani 1 d . . . O371 O 0.5992(3) 0.4883(3) 0.6596(3) 0.0322(9) Uani 1 d . . . O372 O 0.5018(3) 0.6252(3) 0.6733(3) 0.0318(9) Uani 1 d . . . C48 C 0.3160(5) 0.2936(4) 0.4416(4) 0.0296(13) Uani 1 d . . . O481 O 0.3941(3) 0.3589(3) 0.4767(2) 0.0265(8) Uani 1 d . . . O482 O 0.2850(4) 0.2314(3) 0.4857(3) 0.0500(12) Uani 1 d . . . O101 O 0.8149(7) 0.4323(6) 0.6732(6) 0.046(2) Uani 0.50 d P . . H101 H 0.7571 0.4595 0.6754 0.055 Uiso 0.50 calc PR . . C100 C 0.8938(9) 0.4450(9) 0.7482(8) 0.036(3) Uani 0.50 d P . . H10A H 0.9024 0.5185 0.7632 0.043 Uiso 0.50 calc PR . . H10B H 0.9627 0.4187 0.7439 0.043 Uiso 0.50 calc PR . . H10C H 0.8789 0.4077 0.7968 0.043 Uiso 0.50 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0246(3) 0.0188(3) 0.0224(3) 0.0008(3) 0.0093(2) 0.0022(3) N1 0.032(3) 0.022(2) 0.026(2) 0.0030(19) 0.012(2) 0.001(2) C2 0.035(3) 0.026(3) 0.019(2) 0.000(2) 0.010(2) 0.004(3) C3 0.033(3) 0.025(3) 0.026(3) 0.004(2) 0.016(2) 0.001(2) N4 0.018(2) 0.015(2) 0.029(2) 0.0026(18) 0.0088(18) -0.0020(17) C5 0.026(3) 0.020(3) 0.032(3) 0.004(2) 0.007(2) -0.001(2) C6 0.016(3) 0.029(3) 0.032(3) -0.001(2) 0.005(2) -0.002(2) C7 0.020(3) 0.038(3) 0.040(3) 0.004(3) 0.007(2) -0.000(3) C8 0.029(3) 0.045(4) 0.045(4) 0.004(3) 0.021(3) 0.006(3) C9 0.029(3) 0.050(4) 0.042(3) 0.008(3) 0.019(3) 0.018(3) C10 0.020(3) 0.031(3) 0.030(3) 0.003(2) 0.004(2) 0.013(2) C11 0.018(2) 0.031(3) 0.028(3) -0.000(2) 0.003(2) 0.005(2) O12 0.025(2) 0.0183(18) 0.037(2) 0.0046(16) 0.0164(16) 0.0043(16) C13 0.030(3) 0.021(3) 0.030(3) -0.001(2) 0.011(2) 0.010(2) C14 0.027(3) 0.025(3) 0.029(3) 0.003(2) 0.010(2) 0.008(2) C15 0.041(4) 0.034(3) 0.049(4) 0.001(3) 0.020(3) 0.018(3) C16 0.060(4) 0.018(3) 0.047(4) 0.005(3) 0.023(3) 0.016(3) C17 0.045(4) 0.025(3) 0.036(3) 0.001(3) 0.019(3) 0.005(3) C18 0.034(3) 0.024(3) 0.035(3) -0.009(2) 0.014(2) 0.007(3) C19 0.031(3) 0.026(3) 0.031(3) -0.006(2) 0.013(2) -0.004(2) N20 0.023(2) 0.022(2) 0.030(2) -0.0010(19) 0.0128(19) -0.0010(19) C21 0.039(3) 0.030(3) 0.032(3) 0.007(3) 0.016(3) 0.014(3) C22 0.030(3) 0.040(3) 0.024(3) 0.005(3) 0.005(2) 0.010(3) C31 0.023(3) 0.021(3) 0.027(3) 0.002(2) 0.006(2) 0.002(2) C32 0.042(3) 0.039(3) 0.032(3) 0.008(3) 0.007(3) -0.014(3) C33 0.037(4) 0.050(4) 0.029(3) 0.001(3) -0.001(3) -0.007(3) C34 0.027(3) 0.040(4) 0.044(4) -0.010(3) 0.009(3) -0.007(3) C35 0.029(3) 0.028(3) 0.039(3) -0.008(3) 0.017(3) -0.005(2) C36 0.026(3) 0.015(2) 0.027(3) -0.001(2) 0.012(2) 0.000(2) C37 0.026(3) 0.023(3) 0.027(3) -0.000(2) 0.009(2) -0.002(2) O371 0.033(2) 0.023(2) 0.042(2) 0.0018(18) 0.0153(18) -0.0010(17) O372 0.027(2) 0.026(2) 0.045(2) -0.0049(17) 0.0169(18) -0.0004(17) C48 0.040(3) 0.022(3) 0.031(3) 0.001(2) 0.018(3) 0.004(3) O481 0.0256(19) 0.0270(19) 0.0241(18) 0.0002(17) 0.0062(15) 0.0007(18) O482 0.083(4) 0.033(2) 0.039(3) 0.003(2) 0.030(2) -0.021(2) O101 0.039(5) 0.040(5) 0.062(6) -0.030(4) 0.023(5) 0.007(4) C100 0.029(6) 0.030(6) 0.048(7) 0.012(6) 0.015(6) 0.018(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O481 1.925(3) . ? Cu N1 1.995(4) . ? Cu N4 2.029(4) . ? Cu N20 2.041(4) . ? Cu O371 2.387(4) . ? N1 C2 1.462(6) . ? N1 C22 1.465(7) . ? N1 H1 0.9300 . ? C2 C3 1.511(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N4 1.467(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C5 1.482(6) . ? N4 H4 0.9300 . ? C5 C6 1.511(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.391(7) . ? C6 C11 1.393(8) . ? C7 C8 1.382(8) . ? C7 H7 0.9500 . ? C8 C9 1.348(8) . ? C8 H8 0.9500 . ? C9 C10 1.391(8) . ? C9 H9 0.9500 . ? C10 C11 1.387(7) . ? C10 C14 1.470(8) . ? C11 O12 1.385(6) . ? O12 C13 1.382(6) 3_666 ? C13 C18 1.364(8) . ? C13 O12 1.382(6) 3_666 ? C13 C14 1.393(7) 3_666 ? C14 C13 1.393(7) 3_666 ? C14 C15 1.397(8) . ? C15 C16 1.365(9) 3_666 ? C15 H15 0.9500 . ? C16 C15 1.365(9) 3_666 ? C16 C17 1.394(8) . ? C16 H16 0.9500 . ? C17 C18 1.414(7) . ? C17 H17 0.9500 . ? C18 C19 1.506(7) . ? C19 N20 1.460(6) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? N20 C21 1.477(6) . ? N20 H20 0.9300 . ? C21 C22 1.533(7) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C31 C36 1.393(7) . ? C31 C32 1.396(7) . ? C31 C37 1.529(7) 3_666 ? C32 C33 1.366(8) . ? C32 H32 0.9500 . ? C33 C34 1.402(8) . ? C33 H33 0.9500 . ? C34 C35 1.370(8) . ? C34 H34 0.9500 . ? C35 C36 1.402(7) . ? C35 H35 0.9500 . ? C36 C48 1.509(7) . ? C37 O372 1.251(6) . ? C37 O371 1.256(6) . ? C37 C31 1.529(7) 3_666 ? C48 O482 1.224(6) . ? C48 O481 1.273(6) . ? O101 C100 1.238(13) . ? O101 H101 0.8400 . ? C100 H10A 0.9800 . ? C100 H10B 0.9800 . ? C100 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O481 Cu N1 164.18(18) . . ? O481 Cu N4 97.20(15) . . ? N1 Cu N4 85.51(17) . . ? O481 Cu N20 94.71(16) . . ? N1 Cu N20 84.95(17) . . ? N4 Cu N20 166.15(16) . . ? O481 Cu O371 108.15(14) . . ? N1 Cu O371 87.42(16) . . ? N4 Cu O371 89.26(14) . . ? N20 Cu O371 80.30(15) . . ? C2 N1 C22 116.9(4) . . ? C2 N1 Cu 107.2(3) . . ? C22 N1 Cu 107.5(3) . . ? C2 N1 H1 108.3 . . ? C22 N1 H1 108.3 . . ? Cu N1 H1 108.3 . . ? N1 C2 C3 107.7(4) . . ? N1 C2 H2A 110.2 . . ? C3 C2 H2A 110.2 . . ? N1 C2 H2B 110.2 . . ? C3 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? N4 C3 C2 108.4(4) . . ? N4 C3 H3A 110.0 . . ? C2 C3 H3A 110.0 . . ? N4 C3 H3B 110.0 . . ? C2 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? C3 N4 C5 114.0(4) . . ? C3 N4 Cu 107.3(3) . . ? C5 N4 Cu 117.1(3) . . ? C3 N4 H4 105.8 . . ? C5 N4 H4 105.8 . . ? Cu N4 H4 105.8 . . ? N4 C5 C6 114.5(4) . . ? N4 C5 H5A 108.6 . . ? C6 C5 H5A 108.6 . . ? N4 C5 H5B 108.6 . . ? C6 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C7 C6 C11 114.4(5) . . ? C7 C6 C5 124.1(5) . . ? C11 C6 C5 121.5(5) . . ? C8 C7 C6 122.1(6) . . ? C8 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? C9 C8 C7 122.0(5) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C8 C9 C10 118.7(5) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 118.6(5) . . ? C11 C10 C14 105.0(5) . . ? C9 C10 C14 136.4(5) . . ? O12 C11 C10 112.0(5) . . ? O12 C11 C6 123.8(5) . . ? C10 C11 C6 124.2(5) . . ? C13 O12 C11 105.9(4) 3_666 . ? C18 C13 O12 123.5(5) . 3_666 ? C18 C13 C14 124.8(5) . 3_666 ? O12 C13 C14 111.3(5) 3_666 3_666 ? C13 C14 C15 118.2(5) 3_666 . ? C13 C14 C10 105.8(5) 3_666 . ? C15 C14 C10 135.8(5) . . ? C16 C15 C14 119.3(5) 3_666 . ? C16 C15 H15 120.3 3_666 . ? C14 C15 H15 120.3 . . ? C15 C16 C17 120.7(5) 3_666 . ? C15 C16 H16 119.7 3_666 . ? C17 C16 H16 119.7 . . ? C16 C17 C18 121.8(6) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C13 C18 C17 114.9(5) . . ? C13 C18 C19 121.2(5) . . ? C17 C18 C19 123.5(5) . . ? N20 C19 C18 116.4(4) . . ? N20 C19 H19A 108.2 . . ? C18 C19 H19A 108.2 . . ? N20 C19 H19B 108.2 . . ? C18 C19 H19B 108.2 . . ? H19A C19 H19B 107.3 . . ? C19 N20 C21 114.0(4) . . ? C19 N20 Cu 116.6(3) . . ? C21 N20 Cu 108.5(3) . . ? C19 N20 H20 105.6 . . ? C21 N20 H20 105.6 . . ? Cu N20 H20 105.6 . . ? N20 C21 C22 109.1(4) . . ? N20 C21 H21A 109.9 . . ? C22 C21 H21A 109.9 . . ? N20 C21 H21B 109.9 . . ? C22 C21 H21B 109.9 . . ? H21A C21 H21B 108.3 . . ? N1 C22 C21 106.9(4) . . ? N1 C22 H22A 110.3 . . ? C21 C22 H22A 110.3 . . ? N1 C22 H22B 110.3 . . ? C21 C22 H22B 110.3 . . ? H22A C22 H22B 108.6 . . ? C36 C31 C32 119.5(5) . . ? C36 C31 C37 123.9(5) . 3_666 ? C32 C31 C37 116.6(5) . 3_666 ? C33 C32 C31 121.0(5) . . ? C33 C32 H32 119.5 . . ? C31 C32 H32 119.5 . . ? C32 C33 C34 119.7(6) . . ? C32 C33 H33 120.2 . . ? C34 C33 H33 120.2 . . ? C35 C34 C33 119.8(5) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C34 C35 C36 120.8(5) . . ? C34 C35 H35 119.6 . . ? C36 C35 H35 119.6 . . ? C31 C36 C35 119.0(5) . . ? C31 C36 C48 122.0(5) . . ? C35 C36 C48 118.9(5) . . ? O372 C37 O371 126.3(5) . . ? O372 C37 C31 116.5(5) . 3_666 ? O371 C37 C31 116.8(5) . 3_666 ? C37 O371 Cu 129.2(3) . . ? O482 C48 O481 125.1(5) . . ? O482 C48 C36 120.2(5) . . ? O481 C48 C36 114.7(5) . . ? C48 O481 Cu 114.1(3) . . ? C100 O101 H101 109.5 . . ? O101 C100 H10A 109.5 . . ? O101 C100 H10B 109.5 . . ? H10A C100 H10B 109.5 . . ? O101 C100 H10C 109.5 . . ? H10A C100 H10C 109.5 . . ? H10B C100 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 1.086 _refine_diff_density_min -0.618 _refine_diff_density_rms 0.103 _publ_section_references ; Oxford Diffraction Ltd, Crysalis Program (2005) Oxford Diffraction Ltd, Abspack Program (2005) Sheldrick, G.M. (1997) SHELXL program for crystallography refinement. University of Gottingen, Germany. ; #===END #===END data_compound_ni _database_code_depnum_ccdc_archive 'CCDC 774559' #TrackingRef '- Delgado_cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H43.25 Cl4 N6 Ni2 O3.75' _chemical_formula_weight 879.24 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' Ni Ni 0.3393 1.1124 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.285(21) _cell_length_b 14.773(20) _cell_length_c 20.613(24) _cell_angle_alpha 90.00 _cell_angle_beta 102.940(1) _cell_angle_gamma 90.00 _cell_volume 4536(5) _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 needle _exptl_crystal_colour Green _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1821 _exptl_absorpt_coefficient_mu 1.105 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _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 'Image plate' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9030 _diffrn_reflns_av_R_equivalents 0.0794 _diffrn_reflns_av_sigmaI/netI 0.1503 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 22.07 _reflns_number_total 4065 _reflns_number_gt 2643 _reflns_threshold_expression >2sigma(I) _computing_data_collection XDS _computing_cell_refinement XDS _computing_data_reduction DIFABS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1113P)^2^+69.2196P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0001(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4065 _refine_ls_number_parameters 479 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1880 _refine_ls_R_factor_gt 0.1380 _refine_ls_wR_factor_ref 0.3331 _refine_ls_wR_factor_gt 0.3103 _refine_ls_goodness_of_fit_ref 1.181 _refine_ls_restrained_S_all 1.178 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.78454(18) 0.12351(19) 0.18539(14) 0.0484(9) Uani 1 d . . . Ni2 Ni 1.01577(19) -0.1151(2) 0.19181(14) 0.0514(10) Uani 1 d . . . Cl1 Cl 0.6452(4) 0.1970(4) 0.1897(3) 0.0605(18) Uani 1 d . . . Cl2 Cl 0.7429(4) -0.0153(4) 0.2284(3) 0.070(2) Uani 1 d . . . Cl3 Cl 0.9448(4) 0.0462(4) 0.1718(3) 0.0551(17) Uani 1 d . . . Cl4 Cl 1.0716(5) -0.2667(5) 0.2131(4) 0.081(2) Uani 1 d . . . N1 N 0.8257(14) 0.2456(13) 0.1491(10) 0.070(6) Uani 1 d . . . H1 H 0.7831 0.2891 0.1477 0.083 Uiso 1 calc R . . C2 C 0.9106(13) 0.2714(14) 0.1978(10) 0.038(6) Uani 1 d . . . H2A H 0.9582 0.2287 0.1960 0.046 Uiso 1 calc R . . H2B H 0.9299 0.3315 0.1883 0.046 Uiso 1 calc R . . C3 C 0.8885(16) 0.2690(15) 0.2617(13) 0.067(8) Uani 1 d . . . H3A H 0.8402 0.3114 0.2622 0.081 Uiso 1 calc R . . H3B H 0.9403 0.2877 0.2955 0.081 Uiso 1 calc R . . N4 N 0.8602(11) 0.1760(11) 0.2779(8) 0.043(5) Uani 1 d . . . H4 H 0.9120 0.1434 0.2857 0.052 Uiso 1 calc R . . C5 C 0.8253(14) 0.1620(15) 0.3375(11) 0.049(6) Uani 1 d . . . H5A H 0.8084 0.0990 0.3397 0.059 Uiso 1 calc R . . H5B H 0.7717 0.1984 0.3343 0.059 Uiso 1 calc R . . C6 C 0.8982(15) 0.1886(16) 0.4065(11) 0.050(6) Uani 1 d . . . C7 C 0.8861(17) 0.2556(19) 0.4485(12) 0.069(8) Uani 1 d . . . H7 H 0.8357 0.2927 0.4389 0.083 Uiso 1 calc R . . C8 C 0.9560(17) 0.2672(15) 0.5100(11) 0.050(6) Uani 1 d . . . H8 H 0.9504 0.3138 0.5391 0.061 Uiso 1 calc R . . C9 C 1.0219(16) 0.2167(17) 0.5239(12) 0.065(8) Uani 1 d . . . H9 H 1.0678 0.2315 0.5601 0.078 Uiso 1 calc R . . C10 C 1.0311(15) 0.1382(16) 0.4878(13) 0.066(8) Uani 1 d . . . C11 C 0.9708(13) 0.1237(17) 0.4250(11) 0.049(6) Uani 1 d . . . O12 O 0.9912(11) 0.0518(11) 0.3936(8) 0.063(5) Uani 1 d . . . C13 C 1.0739(14) 0.0117(17) 0.4300(12) 0.058(7) Uani 1 d . . . C14 C 1.0944(11) 0.0656(12) 0.4888(9) 0.025(5) Uani 1 d U . . C15 C 1.1787(15) 0.0378(17) 0.5373(12) 0.064(7) Uani 1 d . . . H15 H 1.2023 0.0681 0.5769 0.077 Uiso 1 calc R . . C16 C 1.2156(15) -0.0354(16) 0.5171(12) 0.056(7) Uani 1 d . . . H16 H 1.2674 -0.0566 0.5459 0.067 Uiso 1 calc R . . C17 C 1.1882(15) -0.0831(16) 0.4604(12) 0.060(7) Uani 1 d . . . H17 H 1.2254 -0.1304 0.4538 0.072 Uiso 1 calc R . . C18 C 1.1111(13) -0.0704(14) 0.4105(10) 0.034(5) Uani 1 d . . . C19 C 1.0784(14) -0.1097(16) 0.3434(11) 0.052(7) Uani 1 d . . . H19A H 1.1111 -0.1659 0.3432 0.062 Uiso 1 calc R . . H19B H 1.0163 -0.1265 0.3408 0.062 Uiso 1 calc R . . N20 N 1.0794(13) -0.0678(13) 0.2841(10) 0.062(6) Uani 1 d . . . H20 H 1.0541 -0.0127 0.2872 0.074 Uiso 1 calc R . . C21 C 1.1742(14) -0.0470(16) 0.2819(11) 0.056(7) Uani 1 d . . . H21A H 1.1993 -0.0046 0.3171 0.067 Uiso 1 calc R . . H21B H 1.2097 -0.1020 0.2892 0.067 Uiso 1 calc R . . C22 C 1.1777(14) -0.0083(17) 0.2179(11) 0.058(7) Uani 1 d . . . H22A H 1.2396 0.0008 0.2151 0.069 Uiso 1 calc R . . H22B H 1.1474 0.0499 0.2123 0.069 Uiso 1 calc R . . N23 N 1.1303(10) -0.0754(11) 0.1628(8) 0.046(5) Uani 1 d . . . H23 H 1.1662 -0.1250 0.1653 0.055 Uiso 1 calc R . . C24 C 1.1094(10) -0.0453(11) 0.0929(7) 0.011(4) Uani 1 d U . . H24A H 1.1638 -0.0390 0.0765 0.014 Uiso 1 calc R . . H24B H 1.0782 0.0123 0.0882 0.014 Uiso 1 calc R . . C25 C 1.0473(15) -0.1224(16) 0.0538(11) 0.063(7) Uani 1 d . . . H25A H 1.0257 -0.1053 0.0076 0.075 Uiso 1 calc R . . H25B H 1.0808 -0.1785 0.0554 0.075 Uiso 1 calc R . . N26 N 0.9733(12) -0.1343(13) 0.0851(9) 0.054(5) Uani 1 d . . . H26 H 0.9344 -0.0883 0.0700 0.065 Uiso 1 calc R . . C27 C 0.9217(11) -0.2199(12) 0.0651(9) 0.024(5) Uani 1 d . . . H27A H 0.9621 -0.2714 0.0740 0.029 Uiso 1 calc R . . H27B H 0.8764 -0.2272 0.0909 0.029 Uiso 1 calc R . . C28 C 0.8789(16) -0.2168(17) -0.0058(14) 0.063(7) Uani 1 d . . . C29 C 0.8944(14) -0.2611(17) -0.0566(12) 0.059(7) Uani 1 d . . . H29 H 0.9456 -0.2970 -0.0457 0.070 Uiso 1 calc R . . C30 C 0.8508(14) -0.2671(14) -0.1254(12) 0.051(6) Uani 1 d . . . H30 H 0.8700 -0.3087 -0.1530 0.061 Uiso 1 calc R . . C31 C 0.7739(17) -0.2055(17) -0.1522(12) 0.065(7) Uani 1 d . . . H31 H 0.7453 -0.2007 -0.1969 0.078 Uiso 1 calc R . . C32 C 0.7506(17) -0.1557(18) -0.1003(15) 0.070(8) Uani 1 d . . . C33 C 0.6833(15) -0.0901(17) -0.1039(12) 0.053(7) Uani 1 d . . . C34 C 0.609(2) -0.0589(19) -0.1484(16) 0.093(10) Uani 1 d . . . H34 H 0.5955 -0.0824 -0.1913 0.111 Uiso 1 calc R . . C35 C 0.5567(17) 0.0020(19) -0.1325(13) 0.073(8) Uani 1 d . . . H35 H 0.5072 0.0215 -0.1643 0.088 Uiso 1 calc R . . C36 C 0.5722(16) 0.0377(16) -0.0716(14) 0.070(8) Uani 1 d . . . H36 H 0.5330 0.0834 -0.0655 0.084 Uiso 1 calc R . . C37 C 0.6417(15) 0.0151(16) -0.0136(11) 0.051(6) Uani 1 d . . . C38 C 0.6923(15) -0.0535(18) -0.0369(14) 0.072(9) Uani 1 d . . . O39 O 0.7669(9) -0.0959(10) 0.0072(7) 0.048(4) Uani 1 d . . . C40 C 0.7969(14) -0.1559(14) -0.0366(12) 0.046(6) Uani 1 d . . . C41 C 0.6649(12) 0.0402(13) 0.0600(9) 0.032(5) Uani 1 d U . . H41A H 0.6152 0.0741 0.0699 0.039 Uiso 1 calc R . . H41B H 0.6711 -0.0151 0.0860 0.039 Uiso 1 calc R . . N42 N 0.7444(10) 0.0920(11) 0.0807(8) 0.039(4) Uani 1 d . . . H42 H 0.7887 0.0551 0.0731 0.047 Uiso 1 calc R . . C43 C 0.7547(14) 0.1691(15) 0.0478(11) 0.052(6) Uani 1 d . . . H43A H 0.7019 0.2064 0.0455 0.062 Uiso 1 calc R . . H43B H 0.7572 0.1534 0.0026 0.062 Uiso 1 calc R . . C44 C 0.8412(14) 0.2282(14) 0.0792(12) 0.059(7) Uani 1 d . . . H44A H 0.8962 0.1948 0.0808 0.070 Uiso 1 calc R . . H44B H 0.8425 0.2842 0.0549 0.070 Uiso 1 calc R . . O100 O 0.8932(10) -0.1501(10) 0.2145(8) 0.066(5) Uani 1 d . . . O201 O 0.9126(17) -0.4301(17) 0.1874(12) 0.043(7) Uani 0.50 d P . . O202 O 0.976(5) -0.514(5) 0.085(4) 0.10(2) Uani 0.25 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0453(19) 0.040(2) 0.057(2) 0.0031(14) 0.0045(13) 0.0004(15) Ni2 0.048(2) 0.045(2) 0.057(2) 0.0025(14) 0.0017(14) -0.0017(16) Cl1 0.051(4) 0.061(4) 0.066(5) -0.002(3) 0.003(3) 0.004(3) Cl2 0.074(5) 0.047(4) 0.089(5) 0.000(3) 0.017(4) 0.000(3) Cl3 0.051(4) 0.051(4) 0.057(4) 0.000(3) -0.002(3) 0.001(3) Cl4 0.076(5) 0.069(5) 0.090(6) 0.011(4) 0.001(4) 0.000(4) N1 0.099(18) 0.055(14) 0.059(17) 0.005(11) 0.026(13) 0.019(13) C2 0.039(15) 0.050(15) 0.026(15) 0.016(10) 0.010(10) -0.012(11) C3 0.065(19) 0.038(17) 0.09(2) -0.009(13) 0.000(14) -0.037(14) N4 0.039(11) 0.050(13) 0.034(12) -0.030(9) -0.005(8) 0.003(9) C5 0.045(15) 0.046(15) 0.055(18) -0.032(11) 0.010(11) 0.003(12) C6 0.067(17) 0.049(17) 0.036(17) 0.001(12) 0.011(12) 0.005(14) C7 0.072(19) 0.07(2) 0.06(2) 0.008(15) 0.004(14) 0.004(16) C8 0.075(19) 0.039(16) 0.039(17) -0.010(11) 0.017(13) -0.002(14) C9 0.054(18) 0.05(2) 0.07(2) -0.003(14) -0.020(13) 0.009(15) C10 0.055(17) 0.035(18) 0.10(2) 0.004(14) -0.004(14) 0.004(13) C11 0.030(13) 0.067(19) 0.041(16) 0.022(13) -0.008(10) -0.010(14) O12 0.083(13) 0.049(12) 0.056(12) -0.008(8) 0.013(9) 0.019(10) C13 0.031(15) 0.069(19) 0.068(19) -0.013(13) 0.001(12) 0.000(13) C14 0.025(5) 0.025(5) 0.025(5) 0.0002(11) 0.0054(14) -0.0001(11) C15 0.052(16) 0.064(19) 0.060(18) 0.001(13) -0.022(12) -0.015(14) C16 0.056(17) 0.035(17) 0.08(2) 0.013(13) 0.017(13) 0.030(13) C17 0.051(16) 0.060(18) 0.07(2) -0.037(14) 0.005(13) -0.010(13) C18 0.032(13) 0.045(15) 0.030(16) 0.012(10) 0.021(10) 0.005(11) C19 0.044(15) 0.08(2) 0.039(18) -0.011(14) 0.027(11) 0.020(13) N20 0.073(16) 0.058(15) 0.054(16) -0.011(11) 0.015(10) 0.005(12) C21 0.035(16) 0.08(2) 0.053(19) 0.012(13) 0.003(11) -0.016(13) C22 0.031(14) 0.073(19) 0.061(19) -0.017(14) -0.006(11) -0.009(12) N23 0.034(11) 0.027(11) 0.069(14) 0.016(9) -0.005(9) 0.023(9) C24 0.011(4) 0.011(4) 0.011(4) 0.0000(10) 0.0025(13) 0.0001(11) C25 0.055(17) 0.068(19) 0.058(18) 0.001(13) -0.004(12) 0.023(14) N26 0.053(14) 0.060(15) 0.058(14) 0.014(10) 0.029(10) 0.009(11) C27 0.021(11) 0.018(12) 0.031(14) 0.002(8) -0.001(8) 0.006(9) C28 0.060(18) 0.066(19) 0.06(2) -0.028(15) 0.004(13) -0.001(14) C29 0.045(15) 0.074(19) 0.037(17) 0.007(14) -0.033(12) -0.021(13) C30 0.056(16) 0.024(14) 0.07(2) -0.001(11) 0.017(13) 0.018(12) C31 0.08(2) 0.059(18) 0.048(18) -0.006(13) 0.008(13) -0.003(15) C32 0.047(18) 0.06(2) 0.10(3) -0.031(16) 0.017(16) -0.006(15) C33 0.036(15) 0.065(19) 0.045(18) -0.007(13) -0.017(11) -0.007(14) C34 0.14(3) 0.05(2) 0.09(3) 0.019(15) 0.04(2) 0.02(2) C35 0.059(18) 0.07(2) 0.07(2) -0.012(16) -0.025(14) -0.001(16) C36 0.062(18) 0.048(18) 0.08(2) -0.024(15) -0.015(15) -0.001(13) C37 0.035(15) 0.055(17) 0.066(19) -0.021(12) 0.014(11) 0.009(13) C38 0.032(16) 0.07(2) 0.10(2) 0.023(16) -0.025(14) -0.028(14) O39 0.050(10) 0.053(11) 0.039(10) -0.009(7) 0.008(7) 0.009(8) C40 0.041(15) 0.033(15) 0.061(19) 0.003(12) 0.004(13) -0.014(12) C41 0.032(5) 0.032(5) 0.032(5) -0.0003(11) 0.0073(15) 0.0001(11) N42 0.018(10) 0.024(11) 0.080(15) 0.013(9) 0.020(8) 0.003(8) C43 0.050(15) 0.048(17) 0.051(17) -0.005(12) -0.003(11) -0.005(12) C44 0.052(16) 0.015(14) 0.10(2) 0.012(11) -0.005(13) -0.004(11) O100 0.069(11) 0.035(10) 0.096(14) 0.011(8) 0.019(9) 0.018(8) O201 0.049(18) 0.039(18) 0.040(19) -0.009(13) 0.010(13) 0.009(14) O202 0.12(6) 0.05(5) 0.11(7) 0.03(4) 0.02(5) 0.01(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 Ni1 N1 2.10(2) . ? Ni1 N4 2.141(15) . ? Ni1 N42 2.158(17) . ? Ni1 Cl2 2.377(7) . ? Ni1 Cl1 2.410(6) . ? Ni2 N20 2.055(19) . ? Ni2 N23 2.059(16) . ? Ni2 O100 2.095(16) . ? Ni2 N26 2.168(18) . ? Ni2 Cl4 2.402(8) . ? Ni2 Cl3 2.613(6) . ? N1 C2 1.50(3) . ? N1 C44 1.53(3) . ? C2 C3 1.43(3) . ? C3 N4 1.50(3) . ? N4 C5 1.46(2) . ? C5 C6 1.65(3) . ? C6 C7 1.35(3) . ? C6 C11 1.45(3) . ? C7 C8 1.47(3) . ? C8 C9 1.23(3) . ? C9 C10 1.40(3) . ? C10 C11 1.43(3) . ? C10 C14 1.44(3) . ? C11 O12 1.32(3) . ? O12 C13 1.44(3) . ? C13 C14 1.42(3) . ? C13 C18 1.44(3) . ? C14 C15 1.50(3) . ? C15 C16 1.33(3) . ? C16 C17 1.35(3) . ? C17 C18 1.39(3) . ? C18 C19 1.48(3) . ? C19 N20 1.37(3) . ? N20 C21 1.49(2) . ? C21 C22 1.45(3) . ? C22 N23 1.56(3) . ? N23 C24 1.47(2) . ? C24 C25 1.58(3) . ? C25 N26 1.43(2) . ? N26 C27 1.50(2) . ? C27 C28 1.46(3) . ? C28 C29 1.30(3) . ? C28 C40 1.56(3) . ? C29 C30 1.43(3) . ? C30 C31 1.49(3) . ? C31 C32 1.41(3) . ? C32 C40 1.34(3) . ? C32 C33 1.40(3) . ? C33 C34 1.37(3) . ? C33 C38 1.46(3) . ? C34 C35 1.29(3) . ? C35 C36 1.33(3) . ? C36 C37 1.45(3) . ? C37 C38 1.42(3) . ? C37 C41 1.52(3) . ? C38 O39 1.43(2) . ? O39 C40 1.41(3) . ? C41 N42 1.42(2) . ? N42 C43 1.35(2) . ? C43 C44 1.60(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 Ni1 N4 82.0(8) . . ? N1 Ni1 N42 82.5(7) . . ? N4 Ni1 N42 160.8(6) . . ? N1 Ni1 Cl2 178.1(6) . . ? N4 Ni1 Cl2 96.7(5) . . ? N42 Ni1 Cl2 98.5(5) . . ? N1 Ni1 Cl1 87.9(6) . . ? N4 Ni1 Cl1 96.3(5) . . ? N42 Ni1 Cl1 94.5(4) . . ? Cl2 Ni1 Cl1 93.6(2) . . ? N20 Ni2 N23 85.1(7) . . ? N20 Ni2 O100 98.0(7) . . ? N23 Ni2 O100 175.3(6) . . ? N20 Ni2 N26 162.9(8) . . ? N23 Ni2 N26 79.8(6) . . ? O100 Ni2 N26 96.6(7) . . ? N20 Ni2 Cl4 94.2(6) . . ? N23 Ni2 Cl4 91.7(5) . . ? O100 Ni2 Cl4 91.6(4) . . ? N26 Ni2 Cl4 94.4(5) . . ? N20 Ni2 Cl3 86.0(6) . . ? N23 Ni2 Cl3 92.5(5) . . ? O100 Ni2 Cl3 84.3(4) . . ? N26 Ni2 Cl3 86.5(5) . . ? Cl4 Ni2 Cl3 175.8(3) . . ? C2 N1 C44 112.2(18) . . ? C2 N1 Ni1 105.2(13) . . ? C44 N1 Ni1 108.2(13) . . ? C3 C2 N1 105.2(18) . . ? C2 C3 N4 111.5(18) . . ? C5 N4 C3 119.6(16) . . ? C5 N4 Ni1 118.2(13) . . ? C3 N4 Ni1 105.0(13) . . ? N4 C5 C6 112.9(17) . . ? C7 C6 C11 121(2) . . ? C7 C6 C5 124(2) . . ? C11 C6 C5 113.5(19) . . ? C6 C7 C8 117(2) . . ? C9 C8 C7 122(2) . . ? C8 C9 C10 123(2) . . ? C9 C10 C11 119(2) . . ? C9 C10 C14 139(2) . . ? C11 C10 C14 101(2) . . ? O12 C11 C10 113.0(19) . . ? O12 C11 C6 131(2) . . ? C10 C11 C6 116(2) . . ? C11 O12 C13 110.5(17) . . ? C14 C13 C18 133(2) . . ? C14 C13 O12 102.4(18) . . ? C18 C13 O12 123.8(19) . . ? C13 C14 C10 112.6(19) . . ? C13 C14 C15 114(2) . . ? C10 C14 C15 133(2) . . ? C16 C15 C14 112(2) . . ? C15 C16 C17 129(2) . . ? C16 C17 C18 128(2) . . ? C17 C18 C13 103(2) . . ? C17 C18 C19 134(2) . . ? C13 C18 C19 121.4(18) . . ? N20 C19 C18 126(2) . . ? C19 N20 C21 109.0(18) . . ? C19 N20 Ni2 125.0(17) . . ? C21 N20 Ni2 107.7(14) . . ? C22 C21 N20 110.1(18) . . ? C21 C22 N23 108(2) . . ? C24 N23 C22 119.0(16) . . ? C24 N23 Ni2 111.0(10) . . ? C22 N23 Ni2 104.8(12) . . ? N23 C24 C25 104.8(14) . . ? N26 C25 C24 107.6(18) . . ? C25 N26 C27 113.5(17) . . ? C25 N26 Ni2 110.7(13) . . ? C27 N26 Ni2 114.1(11) . . ? C28 C27 N26 109.8(16) . . ? C29 C28 C27 132(2) . . ? C29 C28 C40 104(2) . . ? C27 C28 C40 124(2) . . ? C28 C29 C30 135(3) . . ? C29 C30 C31 119(2) . . ? C32 C31 C30 110(2) . . ? C40 C32 C33 106(2) . . ? C40 C32 C31 125(3) . . ? C33 C32 C31 129(3) . . ? C34 C33 C32 139(3) . . ? C34 C33 C38 113(3) . . ? C32 C33 C38 107(2) . . ? C35 C34 C33 122(3) . . ? C34 C35 C36 122(3) . . ? C35 C36 C37 129(3) . . ? C38 C37 C36 104(2) . . ? C38 C37 C41 119(2) . . ? C36 C37 C41 137(2) . . ? C37 C38 O39 121(2) . . ? C37 C38 C33 130(2) . . ? O39 C38 C33 109(2) . . ? C40 O39 C38 101.2(19) . . ? C32 C40 O39 117(2) . . ? C32 C40 C28 127(2) . . ? O39 C40 C28 117(2) . . ? N42 C41 C37 115.1(16) . . ? C43 N42 C41 119.5(16) . . ? C43 N42 Ni1 106.3(13) . . ? C41 N42 Ni1 116.7(11) . . ? N42 C43 C44 115.9(18) . . ? N1 C44 C43 100.6(18) . . ? _diffrn_measured_fraction_theta_max 0.691 _diffrn_reflns_theta_full 22.07 _diffrn_measured_fraction_theta_full 0.691 _refine_diff_density_max 1.162 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.119