# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Rocio Garcia-Bueno' 'M. Dolores Santana' 'Gregorio Sanchez' 'Joaquin Garcia' 'Gabriel Garcia' 'Jose Perez' 'Luis Garcia' _publ_contact_author_name 'M. Dolores Santana' _publ_contact_author_email dsl@um.es _publ_section_title ; Mono- and bidentate imidates of five-coordinate nickel(II) with macrocyclic ligands: spectroscopic and photophysical properties ; # Attachment '- CrystalData.cif' data_complex3a _database_code_depnum_ccdc_archive 'CCDC 767981' #TrackingRef '- CrystalData.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H31 N4 Ni O4 S, F6 P, H2 O' _chemical_formula_sum 'C19 H33 F6 N4 Ni O5 P S' _chemical_formula_weight 633.23 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' _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 16.6685(8) _cell_length_b 9.5276(5) _cell_length_c 16.9200(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.7420(10) _cell_angle_gamma 90.00 _cell_volume 2573.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.979 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7989 _exptl_absorpt_correction_T_max 0.9527 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28762 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.13 _reflns_number_total 5927 _reflns_number_gt 5088 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0639P)^2^+9.6814P] 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 5927 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.1612 _refine_ls_wR_factor_gt 0.1545 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _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 O4 O 0.06176(18) 0.9792(3) 0.08806(17) 0.0179(6) Uani 1 1 d . . . C13 C 0.1428(2) 0.6582(4) 0.1637(2) 0.0140(8) Uani 1 1 d . . . O3 O 0.20638(18) 1.0041(3) 0.17098(17) 0.0166(6) Uani 1 1 d . . . O2 O 0.15284(18) 0.5335(3) 0.15085(17) 0.0172(6) Uani 1 1 d . . . C17 C 0.0649(3) 0.8462(5) 0.3565(2) 0.0182(8) Uani 1 1 d . . . H17 H 0.0475 0.8917 0.3988 0.022 Uiso 1 1 calc R . . C18 C 0.0823(2) 0.9263(5) 0.2947(2) 0.0168(8) Uani 1 1 d . . . H18 H 0.0777 1.0257 0.2939 0.020 Uiso 1 1 calc R . . C19 C 0.1067(2) 0.8540(4) 0.2342(2) 0.0127(7) Uani 1 1 d . . . C14 C 0.1145(2) 0.7096(4) 0.2350(2) 0.0147(8) Uani 1 1 d . . . C16 C 0.0723(3) 0.7014(5) 0.3577(3) 0.0206(9) Uani 1 1 d . . . H16 H 0.0599 0.6497 0.4008 0.025 Uiso 1 1 calc R . . C15 C 0.0973(3) 0.6300(5) 0.2972(3) 0.0202(9) Uani 1 1 d . . . H15 H 0.1025 0.5306 0.2982 0.024 Uiso 1 1 calc R . . C3 C 0.1786(3) 0.9887(4) -0.0884(2) 0.0151(8) Uani 1 1 d . . . C1 C 0.2793(2) 0.8018(5) -0.1264(3) 0.0179(8) Uani 1 1 d . . . C2 C 0.2250(3) 0.9314(4) -0.1480(3) 0.0171(8) Uani 1 1 d . . . H2A H 0.1823 0.9126 -0.2012 0.021 Uiso 1 1 calc R . . H2B H 0.2609 1.0081 -0.1581 0.021 Uiso 1 1 calc R . . C5 C 0.0308(3) 0.6720(5) -0.1010(3) 0.0203(9) Uani 1 1 d . . . H5A H 0.0190 0.6958 -0.0484 0.024 Uiso 1 1 calc R . . H5B H -0.0233 0.6494 -0.1420 0.024 Uiso 1 1 calc R . . C4 C 0.0685(3) 0.7998(4) -0.1308(2) 0.0163(8) Uani 1 1 d . . . H4A H 0.0970 0.7698 -0.1719 0.020 Uiso 1 1 calc R . . H4B H 0.0230 0.8655 -0.1584 0.020 Uiso 1 1 calc R . . C6 C 0.0862(3) 0.5429(5) -0.0875(3) 0.0236(9) Uani 1 1 d . . . H6A H 0.0527 0.4598 -0.0816 0.028 Uiso 1 1 calc R . . H6B H 0.1060 0.5281 -0.1367 0.028 Uiso 1 1 calc R . . C7 C 0.2233(3) 0.4430(5) -0.0105(3) 0.0257(10) Uani 1 1 d . . . H7A H 0.1939 0.3519 -0.0241 0.031 Uiso 1 1 calc R . . H7B H 0.2610 0.4362 0.0465 0.031 Uiso 1 1 calc R . . C9 C 0.3322(3) 0.5963(5) -0.0494(3) 0.0244(10) Uani 1 1 d . . . H9A H 0.3667 0.5929 0.0090 0.029 Uiso 1 1 calc R . . H9B H 0.3704 0.5962 -0.0845 0.029 Uiso 1 1 calc R . . C8 C 0.2757(3) 0.4673(5) -0.0688(3) 0.0320(11) Uani 1 1 d . . . H8A H 0.2378 0.4767 -0.1256 0.038 Uiso 1 1 calc R . . H8B H 0.3112 0.3835 -0.0678 0.038 Uiso 1 1 calc R . . C12 C 0.2413(3) 1.0475(4) -0.0112(3) 0.0180(8) Uani 1 1 d . . . H12A H 0.2112 1.0838 0.0265 0.027 Uiso 1 1 calc R . . H12B H 0.2733 1.1237 -0.0267 0.027 Uiso 1 1 calc R . . H12C H 0.2797 0.9729 0.0164 0.027 Uiso 1 1 calc R . . C11 C 0.1205(3) 1.1072(4) -0.1326(3) 0.0195(9) Uani 1 1 d . . . H11A H 0.0902 1.1456 -0.0956 0.029 Uiso 1 1 calc R . . H11B H 0.0802 1.0701 -0.1824 0.029 Uiso 1 1 calc R . . H11C H 0.1539 1.1815 -0.1478 0.029 Uiso 1 1 calc R . . C10 C 0.3269(3) 0.7716(5) -0.1883(3) 0.0260(10) Uani 1 1 d . . . H10A H 0.3612 0.6872 -0.1714 0.039 Uiso 1 1 calc R . . H10B H 0.3632 0.8515 -0.1906 0.039 Uiso 1 1 calc R . . H10C H 0.2872 0.7565 -0.2429 0.039 Uiso 1 1 calc R . . F2 F 0.1456(2) 0.7255(4) -0.3313(2) 0.0432(8) Uani 1 1 d . . . F1 F -0.04540(17) 0.6416(3) -0.4210(2) 0.0385(8) Uani 1 1 d . . . F4 F 0.0211(2) 0.8179(4) -0.3381(2) 0.0603(11) Uani 1 1 d . . . F3 F 0.0519(3) 0.7684(4) -0.4556(2) 0.0647(12) Uani 1 1 d . . . F6 F 0.0796(2) 0.5473(4) -0.4151(2) 0.0570(10) Uani 1 1 d . . . F5 F 0.0503(3) 0.5938(4) -0.2976(2) 0.0598(11) Uani 1 1 d . . . O1 O 0.31947(18) 0.7272(3) 0.11322(19) 0.0187(6) Uani 1 1 d . . . H4 H 0.3600 0.7602 0.0990 0.028 Uiso 1 1 calc R . . O5 O 0.3277(2) 0.7702(4) 0.26871(19) 0.0200(7) Uani 1 1 d . . . H1 H 0.319(4) 0.747(6) 0.158(4) 0.041(18) Uiso 1 1 d . . . H32 H 0.317(3) 0.712(5) 0.291(3) 0.009(12) Uiso 1 1 d . . . H33 H 0.329(4) 0.842(7) 0.293(4) 0.033(16) Uiso 1 1 d . . . Ni1 Ni 0.21237(3) 0.74701(5) 0.01818(3) 0.01082(14) Uani 1 1 d . . . S1 S 0.13287(6) 0.91723(10) 0.14714(6) 0.0114(2) Uani 1 1 d . . . P1 P 0.05066(7) 0.68456(12) -0.37590(7) 0.0185(2) Uani 1 1 d . . . N1 N 0.2818(2) 0.7262(4) -0.0640(2) 0.0180(7) Uani 1 1 d . . . N4 N 0.1541(2) 0.7648(3) 0.1142(2) 0.0126(7) Uani 1 1 d . . . N3 N 0.1601(2) 0.5544(4) -0.0130(2) 0.0168(7) Uani 1 1 d . . . H3 H 0.1387 0.5316 0.0304 0.020 Uiso 1 1 calc R . . N2 N 0.1295(2) 0.8737(3) -0.0619(2) 0.0134(7) Uani 1 1 d . . . H2 H 0.0982 0.9173 -0.0315 0.016 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O4 0.0199(15) 0.0205(15) 0.0152(14) 0.0012(12) 0.0079(12) 0.0051(12) C13 0.0133(18) 0.0141(19) 0.0136(18) 0.0018(15) 0.0026(15) -0.0020(15) O3 0.0233(15) 0.0123(14) 0.0173(14) -0.0011(11) 0.0105(12) -0.0012(11) O2 0.0252(16) 0.0088(13) 0.0192(14) 0.0004(11) 0.0090(12) 0.0020(11) C17 0.0152(19) 0.027(2) 0.0138(19) -0.0021(17) 0.0068(16) 0.0007(17) C18 0.0166(19) 0.019(2) 0.0146(19) -0.0021(16) 0.0048(16) 0.0017(16) C19 0.0108(17) 0.0161(19) 0.0122(18) 0.0002(15) 0.0048(15) -0.0022(15) C14 0.0122(18) 0.0174(19) 0.0137(19) 0.0008(15) 0.0025(15) -0.0015(15) C16 0.019(2) 0.028(2) 0.016(2) 0.0024(17) 0.0067(17) -0.0077(18) C15 0.022(2) 0.018(2) 0.022(2) 0.0037(17) 0.0082(18) -0.0038(17) C3 0.0183(19) 0.0164(19) 0.0131(18) 0.0015(15) 0.0083(16) 0.0010(16) C1 0.0108(18) 0.025(2) 0.019(2) -0.0073(17) 0.0064(16) -0.0047(16) C2 0.019(2) 0.019(2) 0.018(2) -0.0005(16) 0.0119(16) -0.0011(16) C5 0.0135(19) 0.023(2) 0.024(2) -0.0002(17) 0.0044(17) -0.0043(17) C4 0.0147(19) 0.020(2) 0.0142(19) 0.0000(16) 0.0036(16) 0.0013(16) C6 0.030(2) 0.017(2) 0.020(2) -0.0032(17) 0.0010(19) -0.0057(18) C7 0.031(2) 0.014(2) 0.032(3) -0.0047(18) 0.008(2) 0.0039(18) C9 0.021(2) 0.026(2) 0.029(2) -0.0052(19) 0.0118(19) 0.0075(18) C8 0.038(3) 0.022(2) 0.038(3) -0.010(2) 0.015(2) 0.008(2) C12 0.019(2) 0.017(2) 0.019(2) -0.0009(16) 0.0070(17) -0.0028(16) C11 0.022(2) 0.019(2) 0.020(2) 0.0030(16) 0.0095(17) -0.0011(17) C10 0.025(2) 0.031(3) 0.027(2) -0.0034(19) 0.016(2) 0.0044(19) F2 0.0294(17) 0.048(2) 0.0471(19) -0.0045(15) 0.0027(14) -0.0071(14) F1 0.0205(14) 0.0465(19) 0.0485(19) -0.0182(15) 0.0102(13) 0.0005(13) F4 0.059(2) 0.049(2) 0.063(2) -0.0318(19) 0.0021(19) 0.0236(18) F3 0.082(3) 0.084(3) 0.0289(18) 0.0102(18) 0.0171(19) -0.039(2) F6 0.042(2) 0.057(2) 0.064(2) -0.0276(19) 0.0021(17) 0.0138(17) F5 0.078(3) 0.059(2) 0.0374(19) 0.0094(17) 0.0097(18) -0.033(2) O1 0.0150(14) 0.0295(17) 0.0131(14) -0.0010(12) 0.0063(12) -0.0010(12) O5 0.0340(19) 0.0105(16) 0.0161(15) 0.0007(13) 0.0084(14) -0.0027(13) Ni1 0.0119(2) 0.0106(2) 0.0112(2) -0.00180(18) 0.00527(18) 0.00067(18) S1 0.0143(4) 0.0103(4) 0.0118(4) 0.0002(3) 0.0073(4) 0.0010(3) P1 0.0173(5) 0.0242(6) 0.0166(5) 0.0001(4) 0.0090(4) -0.0006(4) N1 0.0163(17) 0.0214(19) 0.0172(17) -0.0034(14) 0.0065(14) 0.0017(14) N4 0.0154(16) 0.0100(15) 0.0139(16) -0.0012(12) 0.0066(13) 0.0006(12) N3 0.0210(18) 0.0149(17) 0.0149(17) -0.0018(13) 0.0059(14) 0.0028(14) N2 0.0151(16) 0.0129(16) 0.0154(16) -0.0009(13) 0.0094(13) -0.0018(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O4 S1 1.439(3) . ? C13 O2 1.228(5) . ? C13 N4 1.364(5) . ? C13 C14 1.499(5) . ? O3 S1 1.437(3) . ? C17 C16 1.385(6) . ? C17 C18 1.392(6) . ? C18 C19 1.388(5) . ? C19 C14 1.382(6) . ? C19 S1 1.758(4) . ? C14 C15 1.392(6) . ? C16 C15 1.389(6) . ? C3 N2 1.510(5) . ? C3 C12 1.526(6) . ? C3 C11 1.534(6) . ? C3 C2 1.537(5) . ? C1 N1 1.270(6) . ? C1 C10 1.512(6) . ? C1 C2 1.512(6) . ? C5 C6 1.516(6) . ? C5 C4 1.522(6) . ? C4 N2 1.485(5) . ? C6 N3 1.491(5) . ? C7 N3 1.487(5) . ? C7 C8 1.514(7) . ? C9 N1 1.476(5) . ? C9 C8 1.525(7) . ? F2 P1 1.592(3) . ? F1 P1 1.615(3) . ? F4 P1 1.564(3) . ? F3 P1 1.572(3) . ? F6 P1 1.603(3) . ? F5 P1 1.583(4) . ? O1 Ni1 2.038(3) . ? Ni1 N2 2.030(3) . ? Ni1 N3 2.035(3) . ? Ni1 N1 2.059(3) . ? Ni1 N4 2.126(3) . ? S1 N4 1.631(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 O2 C13 N4 124.1(4) . . ? O2 C13 C14 123.3(4) . . ? N4 C13 C14 112.5(3) . . ? C16 C17 C18 121.3(4) . . ? C19 C18 C17 116.8(4) . . ? C14 C19 C18 122.2(4) . . ? C14 C19 S1 107.8(3) . . ? C18 C19 S1 130.1(3) . . ? C19 C14 C15 120.8(4) . . ? C19 C14 C13 111.5(3) . . ? C15 C14 C13 127.7(4) . . ? C17 C16 C15 121.5(4) . . ? C16 C15 C14 117.4(4) . . ? N2 C3 C12 108.0(3) . . ? N2 C3 C11 111.0(3) . . ? C12 C3 C11 109.1(3) . . ? N2 C3 C2 110.8(3) . . ? C12 C3 C2 110.0(3) . . ? C11 C3 C2 108.0(3) . . ? N1 C1 C10 124.8(4) . . ? N1 C1 C2 122.5(4) . . ? C10 C1 C2 112.7(4) . . ? C1 C2 C3 120.8(3) . . ? C6 C5 C4 114.0(4) . . ? N2 C4 C5 112.0(3) . . ? N3 C6 C5 112.7(3) . . ? N3 C7 C8 114.1(4) . . ? N1 C9 C8 110.8(4) . . ? C7 C8 C9 114.7(4) . . ? N2 Ni1 N3 101.83(13) . . ? N2 Ni1 O1 148.69(13) . . ? N3 Ni1 O1 109.47(13) . . ? N2 Ni1 N1 90.75(13) . . ? N3 Ni1 N1 91.15(14) . . ? O1 Ni1 N1 89.35(13) . . ? N2 Ni1 N4 95.16(13) . . ? N3 Ni1 N4 90.82(13) . . ? O1 Ni1 N4 83.90(13) . . ? N1 Ni1 N4 173.25(13) . . ? O3 S1 O4 115.09(18) . . ? O3 S1 N4 110.96(17) . . ? O4 S1 N4 110.12(17) . . ? O3 S1 C19 111.05(17) . . ? O4 S1 C19 111.66(18) . . ? N4 S1 C19 96.44(18) . . ? F4 P1 F3 91.2(2) . . ? F4 P1 F5 91.4(2) . . ? F3 P1 F5 177.4(2) . . ? F4 P1 F2 89.7(2) . . ? F3 P1 F2 91.4(2) . . ? F5 P1 F2 88.9(2) . . ? F4 P1 F6 179.2(2) . . ? F3 P1 F6 88.8(2) . . ? F5 P1 F6 88.6(2) . . ? F2 P1 F6 91.09(18) . . ? F4 P1 F1 90.73(18) . . ? F3 P1 F1 88.9(2) . . ? F5 P1 F1 90.83(19) . . ? F2 P1 F1 179.5(2) . . ? F6 P1 F1 88.49(17) . . ? C1 N1 C9 119.7(4) . . ? C1 N1 Ni1 128.1(3) . . ? C9 N1 Ni1 111.8(3) . . ? C13 N4 S1 111.8(3) . . ? C13 N4 Ni1 125.8(3) . . ? S1 N4 Ni1 121.61(18) . . ? C7 N3 C6 112.2(3) . . ? C7 N3 Ni1 112.9(3) . . ? C6 N3 Ni1 118.3(3) . . ? C4 N2 C3 114.7(3) . . ? C4 N2 Ni1 115.0(2) . . ? C3 N2 Ni1 107.9(2) . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 0.50 _diffrn_measured_fraction_theta_full 0.000 _refine_diff_density_max 1.450 _refine_diff_density_min -0.818 _refine_diff_density_rms 0.127 #===END data_complex3b _database_code_depnum_ccdc_archive 'CCDC 767982' #TrackingRef '- CrystalData.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H33 N4 Ni O4 S, C7 H4 N O3 S, C3 H6 O' _chemical_formula_sum 'C30 H43 N5 Ni O8 S2' _chemical_formula_weight 724.52 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3096(5) _cell_length_b 13.9023(9) _cell_length_c 15.1795(9) _cell_angle_alpha 73.4690(10) _cell_angle_beta 77.9510(10) _cell_angle_gamma 82.3750(10) _cell_volume 1639.03(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 0.777 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7948 _exptl_absorpt_correction_T_max 0.9549 _exptl_absorpt_process_details ? _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 ? _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 18799 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 28.02 _reflns_number_total 7289 _reflns_number_gt 6358 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0676P)^2^+3.4422P] 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 7289 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1479 _refine_ls_wR_factor_gt 0.1376 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 Ni1 Ni 0.86799(5) 0.00597(3) 0.29759(3) 0.01187(12) Uani 1 1 d . . . S1 S 1.16717(9) 0.31825(6) 0.25839(6) 0.01475(18) Uani 1 1 d . . . S2 S 1.38257(10) 0.69163(6) 0.27913(6) 0.01677(18) Uani 1 1 d . . . O1 O 1.1171(3) 0.01854(18) 0.27177(17) 0.0158(5) Uani 1 1 d . . . H4 H 1.1607 -0.0048 0.2279 0.024 Uiso 1 1 calc R . . N2 N 0.9225(3) -0.1457(2) 0.32156(19) 0.0142(5) Uani 1 1 d . . . H2 H 1.0347 -0.1543 0.3116 0.017 Uiso 1 1 calc R . . N4 N 1.0868(3) 0.2140(2) 0.2653(2) 0.0155(6) Uani 1 1 d . . . O2 O 0.8335(3) 0.14819(17) 0.31517(16) 0.0164(5) Uani 1 1 d . . . N1 N 0.6273(3) -0.0164(2) 0.36013(19) 0.0140(5) Uani 1 1 d . . . O3 O 1.2292(3) 0.36799(18) 0.16305(17) 0.0213(5) Uani 1 1 d . . . O4 O 1.2820(3) 0.29725(18) 0.32191(17) 0.0193(5) Uani 1 1 d . . . N3 N 0.8122(3) 0.0436(2) 0.16564(19) 0.0150(5) Uani 1 1 d . . . C15 C 0.8572(4) 0.3170(2) 0.3190(2) 0.0141(6) Uani 1 1 d . . . C20 C 0.9805(4) 0.3813(2) 0.3016(2) 0.0151(6) Uani 1 1 d . . . C19 C 0.9509(4) 0.4758(3) 0.3167(2) 0.0195(7) Uani 1 1 d . . . H19 H 1.0352 0.5180 0.3049 0.023 Uiso 1 1 calc R . . C16 C 0.6946(4) 0.3465(3) 0.3516(2) 0.0184(7) Uani 1 1 d . . . H16 H 0.6107 0.3042 0.3624 0.022 Uiso 1 1 calc R . . C14 C 0.9251(4) 0.2189(2) 0.2989(2) 0.0142(6) Uani 1 1 d . . . O5 O 1.4756(3) 0.67769(18) 0.35269(17) 0.0214(5) Uani 1 1 d . . . O6 O 1.2666(3) 0.6178(2) 0.29321(19) 0.0261(6) Uani 1 1 d . . . N5 N 1.2930(3) 0.8050(2) 0.2549(2) 0.0184(6) Uani 1 1 d . . . C3 C 0.8688(4) -0.1893(2) 0.4242(2) 0.0152(6) Uani 1 1 d . . . C21 C 1.3553(4) 0.8580(3) 0.1688(2) 0.0169(7) Uani 1 1 d . . . C7 C 0.6691(4) 0.1217(3) 0.1590(2) 0.0175(7) Uani 1 1 d . . . H7A H 0.6484 0.1402 0.0955 0.021 Uiso 1 1 calc R . . H7B H 0.7013 0.1813 0.1700 0.021 Uiso 1 1 calc R . . C1 C 0.5705(4) -0.0988(2) 0.4127(2) 0.0150(6) Uani 1 1 d . . . C22 C 1.4883(4) 0.8003(2) 0.1160(2) 0.0162(6) Uani 1 1 d . . . C27 C 1.5173(4) 0.7036(3) 0.1702(2) 0.0160(6) Uani 1 1 d . . . C9 C 0.5126(4) 0.0719(2) 0.3288(2) 0.0165(6) Uani 1 1 d . . . H9A H 0.5471 0.1305 0.3402 0.020 Uiso 1 1 calc R . . H9B H 0.4026 0.0599 0.3648 0.020 Uiso 1 1 calc R . . C17 C 0.6613(4) 0.4411(3) 0.3677(3) 0.0227(7) Uani 1 1 d . . . H17 H 0.5536 0.4625 0.3901 0.027 Uiso 1 1 calc R . . C26 C 1.6330(4) 0.6343(3) 0.1376(3) 0.0212(7) Uani 1 1 d . . . H26 H 1.6520 0.5695 0.1747 0.025 Uiso 1 1 calc R . . C5 C 0.8962(4) -0.1372(2) 0.1590(2) 0.0164(6) Uani 1 1 d . . . H5A H 0.8873 -0.1802 0.1202 0.020 Uiso 1 1 calc R . . H5B H 1.0071 -0.1150 0.1413 0.020 Uiso 1 1 calc R . . C4 C 0.8712(4) -0.1987(3) 0.2606(2) 0.0178(7) Uani 1 1 d . . . H4A H 0.7557 -0.2115 0.2821 0.021 Uiso 1 1 calc R . . H4B H 0.9350 -0.2631 0.2653 0.021 Uiso 1 1 calc R . . C8 C 0.5076(4) 0.0926(3) 0.2253(2) 0.0179(7) Uani 1 1 d . . . H8A H 0.4228 0.1463 0.2096 0.021 Uiso 1 1 calc R . . H8B H 0.4752 0.0328 0.2147 0.021 Uiso 1 1 calc R . . C10 C 0.3884(4) -0.1150(3) 0.4448(2) 0.0185(7) Uani 1 1 d . . . H10A H 0.3242 -0.0543 0.4201 0.028 Uiso 1 1 calc R . . H10B H 0.3628 -0.1326 0.5118 0.028 Uiso 1 1 calc R . . H10C H 0.3628 -0.1685 0.4228 0.028 Uiso 1 1 calc R . . O7 O 1.3088(3) 0.94780(18) 0.13356(17) 0.0203(5) Uani 1 1 d . . . C24 C 1.6917(4) 0.7639(3) -0.0081(2) 0.0208(7) Uani 1 1 d . . . H24 H 1.7510 0.7835 -0.0686 0.025 Uiso 1 1 calc R . . C23 C 1.5761(4) 0.8328(3) 0.0265(2) 0.0188(7) Uani 1 1 d . . . H23 H 1.5588 0.8984 -0.0096 0.023 Uiso 1 1 calc R . . C25 C 1.7197(4) 0.6665(3) 0.0464(3) 0.0236(8) Uani 1 1 d . . . H25 H 1.7975 0.6220 0.0218 0.028 Uiso 1 1 calc R . . C18 C 0.7876(4) 0.5048(3) 0.3506(3) 0.0215(7) Uani 1 1 d . . . H18 H 0.7624 0.5678 0.3620 0.026 Uiso 1 1 calc R . . C12 C 0.9275(4) -0.1234(3) 0.4752(2) 0.0175(7) Uani 1 1 d . . . H12A H 1.0454 -0.1227 0.4591 0.026 Uiso 1 1 calc R . . H12B H 0.8959 -0.1503 0.5414 0.026 Uiso 1 1 calc R . . H12C H 0.8778 -0.0561 0.4569 0.026 Uiso 1 1 calc R . . C11 C 0.9459(4) -0.2974(3) 0.4569(2) 0.0193(7) Uani 1 1 d . . . H11A H 1.0641 -0.2975 0.4419 0.029 Uiso 1 1 calc R . . H11B H 0.9097 -0.3398 0.4260 0.029 Uiso 1 1 calc R . . H11C H 0.9122 -0.3222 0.5233 0.029 Uiso 1 1 calc R . . C6 C 0.7734(4) -0.0453(3) 0.1392(2) 0.0176(7) Uani 1 1 d . . . H6A H 0.7692 -0.0256 0.0730 0.021 Uiso 1 1 calc R . . H6B H 0.6646 -0.0641 0.1728 0.021 Uiso 1 1 calc R . . C2 C 0.6799(4) -0.1914(2) 0.4487(2) 0.0152(6) Uani 1 1 d . . . H2A H 0.6512 -0.2453 0.4274 0.018 Uiso 1 1 calc R . . H2B H 0.6502 -0.2102 0.5163 0.018 Uiso 1 1 calc R . . C13 C 0.9520(4) 0.0918(3) 0.0962(2) 0.0189(7) Uani 1 1 d . . . H13A H 1.0483 0.0453 0.0973 0.028 Uiso 1 1 calc R . . H13B H 0.9741 0.1506 0.1115 0.028 Uiso 1 1 calc R . . H13C H 0.9240 0.1108 0.0350 0.028 Uiso 1 1 calc R . . O8 O 0.8988(4) 0.3467(4) 0.0829(2) 0.0598(12) Uani 1 1 d . . . C30 C 0.6027(6) 0.3926(3) 0.0822(3) 0.0351(10) Uani 1 1 d . . . H60A H 0.5948 0.3917 0.1465 0.053 Uiso 1 1 calc R . . H60B H 0.5372 0.3425 0.0785 0.053 Uiso 1 1 calc R . . H60C H 0.5629 0.4578 0.0482 0.053 Uiso 1 1 calc R . . C29 C 0.7883(5) 0.3696(3) 0.0387(3) 0.0345(9) Uani 1 1 d . . . C28 C 0.8165(5) 0.3693(4) -0.0661(3) 0.0405(12) Uani 1 1 d . . . H62A H 0.9318 0.3547 -0.0877 0.061 Uiso 1 1 calc R . . H62B H 0.7806 0.4341 -0.1025 0.061 Uiso 1 1 calc R . . H62C H 0.7545 0.3189 -0.0725 0.061 Uiso 1 1 calc R . . H50 H 1.142(6) 0.078(4) 0.256(3) 0.039(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0094(2) 0.0125(2) 0.0145(2) -0.00564(16) -0.00219(14) 0.00130(14) S1 0.0125(4) 0.0145(4) 0.0182(4) -0.0070(3) -0.0019(3) 0.0002(3) S2 0.0146(4) 0.0162(4) 0.0196(4) -0.0073(3) -0.0016(3) 0.0017(3) O1 0.0129(11) 0.0133(12) 0.0216(12) -0.0068(10) -0.0014(9) 0.0002(9) N2 0.0115(12) 0.0158(13) 0.0169(13) -0.0081(11) -0.0012(10) -0.0003(10) N4 0.0131(13) 0.0144(13) 0.0211(14) -0.0089(11) -0.0018(11) -0.0006(10) O2 0.0129(11) 0.0148(11) 0.0226(12) -0.0081(9) -0.0025(9) 0.0012(9) N1 0.0111(12) 0.0168(13) 0.0155(13) -0.0081(11) -0.0025(10) 0.0023(10) O3 0.0201(12) 0.0209(12) 0.0224(13) -0.0074(10) 0.0009(10) -0.0035(10) O4 0.0135(11) 0.0223(12) 0.0245(13) -0.0091(10) -0.0059(9) 0.0004(9) N3 0.0119(13) 0.0154(13) 0.0186(14) -0.0068(11) -0.0034(10) 0.0021(10) C15 0.0158(15) 0.0137(15) 0.0132(15) -0.0040(12) -0.0048(12) 0.0023(12) C20 0.0159(15) 0.0151(15) 0.0147(15) -0.0053(12) -0.0048(12) 0.0034(12) C19 0.0184(16) 0.0153(16) 0.0251(18) -0.0045(14) -0.0063(13) 0.0002(13) C16 0.0137(15) 0.0191(16) 0.0223(17) -0.0062(14) -0.0022(13) -0.0003(12) C14 0.0142(15) 0.0151(15) 0.0142(15) -0.0046(12) -0.0051(12) 0.0016(12) O5 0.0219(12) 0.0212(12) 0.0215(13) -0.0082(10) -0.0058(10) 0.0050(10) O6 0.0245(13) 0.0236(13) 0.0296(14) -0.0086(11) 0.0009(11) -0.0054(11) N5 0.0146(13) 0.0186(14) 0.0208(15) -0.0073(12) -0.0006(11) 0.0034(11) C3 0.0147(15) 0.0153(15) 0.0150(15) -0.0042(12) -0.0016(12) 0.0002(12) C21 0.0128(15) 0.0193(16) 0.0223(17) -0.0095(14) -0.0066(12) 0.0004(12) C7 0.0156(16) 0.0171(16) 0.0192(16) -0.0044(13) -0.0051(13) 0.0026(12) C1 0.0126(15) 0.0189(16) 0.0165(15) -0.0098(13) -0.0035(12) 0.0016(12) C22 0.0121(15) 0.0183(16) 0.0217(17) -0.0107(13) -0.0039(12) -0.0005(12) C27 0.0125(15) 0.0207(16) 0.0180(16) -0.0112(13) -0.0018(12) -0.0003(12) C9 0.0132(15) 0.0148(15) 0.0211(17) -0.0056(13) -0.0027(12) 0.0018(12) C17 0.0169(17) 0.0214(18) 0.0297(19) -0.0105(15) -0.0031(14) 0.0045(13) C26 0.0216(17) 0.0191(17) 0.0246(18) -0.0101(14) -0.0056(14) 0.0049(14) C5 0.0143(15) 0.0178(16) 0.0186(16) -0.0092(13) -0.0022(12) 0.0012(12) C4 0.0180(16) 0.0158(16) 0.0198(17) -0.0072(13) -0.0009(13) -0.0008(12) C8 0.0124(15) 0.0189(16) 0.0233(17) -0.0069(14) -0.0059(13) 0.0028(12) C10 0.0137(15) 0.0206(17) 0.0203(17) -0.0056(14) -0.0015(12) -0.0006(13) O7 0.0183(12) 0.0166(12) 0.0249(13) -0.0065(10) -0.0033(10) 0.0036(9) C24 0.0163(16) 0.0296(19) 0.0187(17) -0.0124(15) 0.0004(13) -0.0018(14) C23 0.0148(16) 0.0222(17) 0.0221(17) -0.0084(14) -0.0050(13) -0.0021(13) C25 0.0177(17) 0.0292(19) 0.0280(19) -0.0182(16) -0.0027(14) 0.0050(14) C18 0.0201(17) 0.0156(16) 0.0309(19) -0.0112(15) -0.0067(14) 0.0058(13) C12 0.0140(15) 0.0206(17) 0.0192(16) -0.0080(14) -0.0035(12) 0.0011(13) C11 0.0192(16) 0.0168(16) 0.0199(17) -0.0041(13) -0.0046(13) 0.0057(13) C6 0.0142(15) 0.0214(17) 0.0191(16) -0.0089(14) -0.0039(12) 0.0013(13) C2 0.0162(15) 0.0146(15) 0.0146(15) -0.0043(12) -0.0015(12) -0.0017(12) C13 0.0148(16) 0.0216(17) 0.0185(16) -0.0035(14) -0.0024(13) 0.0008(13) O8 0.0210(15) 0.126(4) 0.0293(17) -0.017(2) -0.0120(13) 0.0091(18) C30 0.048(3) 0.0120(17) 0.035(2) -0.0059(16) 0.0099(19) 0.0065(16) C29 0.031(2) 0.029(2) 0.044(2) -0.0104(19) -0.0063(18) -0.0055(17) C28 0.025(2) 0.063(3) 0.022(2) 0.014(2) -0.0119(16) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N2 2.040(3) . ? Ni1 O2 2.045(2) . ? Ni1 O1 2.046(2) . ? Ni1 N1 2.050(3) . ? Ni1 N3 2.056(3) . ? S1 O3 1.432(3) . ? S1 O4 1.441(2) . ? S1 N4 1.642(3) . ? S1 C20 1.774(3) . ? S2 O5 1.442(3) . ? S2 O6 1.442(3) . ? S2 N5 1.627(3) . ? S2 C27 1.771(3) . ? N2 C4 1.490(4) . ? N2 C3 1.496(4) . ? N4 C14 1.334(4) . ? O2 C14 1.260(4) . ? N1 C1 1.280(4) . ? N1 C9 1.479(4) . ? N3 C13 1.484(4) . ? N3 C6 1.494(4) . ? N3 C7 1.500(4) . ? C15 C20 1.385(4) . ? C15 C16 1.389(4) . ? C15 C14 1.494(4) . ? C20 C19 1.378(5) . ? C19 C18 1.396(5) . ? C16 C17 1.388(5) . ? N5 C21 1.337(4) . ? C3 C12 1.535(4) . ? C3 C2 1.537(4) . ? C3 C11 1.538(4) . ? C21 O7 1.254(4) . ? C21 C22 1.506(4) . ? C7 C8 1.525(4) . ? C1 C2 1.509(4) . ? C1 C10 1.516(4) . ? C22 C23 1.382(5) . ? C22 C27 1.382(5) . ? C27 C26 1.387(5) . ? C9 C8 1.524(5) . ? C17 C18 1.398(5) . ? C26 C25 1.397(5) . ? C5 C4 1.522(5) . ? C5 C6 1.526(4) . ? C24 C25 1.390(5) . ? C24 C23 1.395(5) . ? O8 C29 1.205(5) . ? C30 C29 1.575(6) . ? C29 C28 1.560(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 N2 Ni1 O2 161.45(10) . . ? N2 Ni1 O1 86.82(10) . . ? O2 Ni1 O1 88.42(9) . . ? N2 Ni1 N1 90.39(11) . . ? O2 Ni1 N1 89.42(10) . . ? O1 Ni1 N1 164.51(10) . . ? N2 Ni1 N3 101.67(11) . . ? O2 Ni1 N3 96.87(10) . . ? O1 Ni1 N3 102.85(10) . . ? N1 Ni1 N3 92.64(11) . . ? O3 S1 O4 116.24(15) . . ? O3 S1 N4 110.63(15) . . ? O4 S1 N4 109.49(15) . . ? O3 S1 C20 111.18(15) . . ? O4 S1 C20 111.28(15) . . ? N4 S1 C20 96.21(15) . . ? O5 S2 O6 116.14(16) . . ? O5 S2 N5 110.54(15) . . ? O6 S2 N5 110.84(16) . . ? O5 S2 C27 110.33(15) . . ? O6 S2 C27 110.67(15) . . ? N5 S2 C27 96.62(15) . . ? C4 N2 C3 115.1(2) . . ? C4 N2 Ni1 118.7(2) . . ? C3 N2 Ni1 106.15(19) . . ? C14 N4 S1 111.4(2) . . ? C14 O2 Ni1 134.7(2) . . ? C1 N1 C9 120.0(3) . . ? C1 N1 Ni1 126.9(2) . . ? C9 N1 Ni1 112.7(2) . . ? C13 N3 C6 109.3(3) . . ? C13 N3 C7 105.4(2) . . ? C6 N3 C7 109.6(2) . . ? C13 N3 Ni1 109.9(2) . . ? C6 N3 Ni1 112.6(2) . . ? C7 N3 Ni1 109.8(2) . . ? C20 C15 C16 120.6(3) . . ? C20 C15 C14 111.3(3) . . ? C16 C15 C14 128.2(3) . . ? C19 C20 C15 122.8(3) . . ? C19 C20 S1 130.2(3) . . ? C15 C20 S1 107.0(2) . . ? C20 C19 C18 116.5(3) . . ? C17 C16 C15 117.8(3) . . ? O2 C14 N4 125.0(3) . . ? O2 C14 C15 120.9(3) . . ? N4 C14 C15 114.1(3) . . ? C21 N5 S2 111.4(2) . . ? N2 C3 C12 107.7(3) . . ? N2 C3 C2 110.5(3) . . ? C12 C3 C2 110.3(3) . . ? N2 C3 C11 111.6(3) . . ? C12 C3 C11 108.4(3) . . ? C2 C3 C11 108.4(3) . . ? O7 C21 N5 124.0(3) . . ? O7 C21 C22 121.8(3) . . ? N5 C21 C22 114.2(3) . . ? N3 C7 C8 116.6(3) . . ? N1 C1 C2 123.0(3) . . ? N1 C1 C10 124.4(3) . . ? C2 C1 C10 112.7(3) . . ? C23 C22 C27 120.9(3) . . ? C23 C22 C21 128.5(3) . . ? C27 C22 C21 110.6(3) . . ? C22 C27 C26 122.2(3) . . ? C22 C27 S2 107.3(2) . . ? C26 C27 S2 130.5(3) . . ? N1 C9 C8 111.5(3) . . ? C16 C17 C18 120.8(3) . . ? C27 C26 C25 116.9(3) . . ? C4 C5 C6 114.0(3) . . ? N2 C4 C5 111.6(3) . . ? C9 C8 C7 115.4(3) . . ? C25 C24 C23 121.1(3) . . ? C22 C23 C24 117.7(3) . . ? C24 C25 C26 121.1(3) . . ? C19 C18 C17 121.5(3) . . ? N3 C6 C5 114.6(3) . . ? C1 C2 C3 120.3(3) . . ? O8 C29 C28 121.8(4) . . ? O8 C29 C30 123.9(4) . . ? C28 C29 C30 114.1(4) . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 0.50 _diffrn_measured_fraction_theta_full 0.000 _refine_diff_density_max 2.597 _refine_diff_density_min -0.839 _refine_diff_density_rms 0.136 #===END data_complex4b _database_code_depnum_ccdc_archive 'CCDC 767983' #TrackingRef '- CrystalData.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26.50 H37 F6 N4 Ni O2.50 P' _chemical_formula_weight 655.28 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 7.9767(4) _cell_length_b 14.7743(7) _cell_length_c 24.1568(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.5620(10) _cell_angle_gamma 90.00 _cell_volume 2837.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1364 _exptl_absorpt_coefficient_mu 0.814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8607 _exptl_absorpt_correction_T_max 0.9377 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32147 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.18 _reflns_number_total 6571 _reflns_number_gt 5279 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0882P)^2^+4.2712P] 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 6571 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1375 _refine_ls_wR_factor_gt 0.1261 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_restrained_S_all 0.905 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C13 C 0.4371(4) 0.9790(2) 0.24938(12) 0.0245(6) Uani 1 1 d . . . H13A H 0.5433 1.0097 0.2438 0.037 Uiso 1 1 calc R . . H13B H 0.4277 0.9697 0.2892 0.037 Uiso 1 1 calc R . . H13C H 0.3429 1.0162 0.2340 0.037 Uiso 1 1 calc R . . C11 C 0.3650(4) 0.9098(2) 0.01677(12) 0.0246(6) Uani 1 1 d . . . H11A H 0.3249 0.9725 0.0143 0.037 Uiso 1 1 calc R . . H11B H 0.3757 0.8862 -0.0207 0.037 Uiso 1 1 calc R . . H11C H 0.4748 0.9079 0.0380 0.037 Uiso 1 1 calc R . . Ni1 Ni 0.46244(4) 0.90683(2) 0.138121(14) 0.01329(11) Uani 1 1 d . . . P1 P 1.06681(9) 0.57113(5) 0.17322(3) 0.01875(17) Uani 1 1 d . . . O2 O 0.2348(2) 1.10161(13) 0.09421(9) 0.0223(4) Uani 1 1 d . . . F1 F 0.9953(3) 0.65209(14) 0.20805(9) 0.0375(5) Uani 1 1 d . . . O1 O 0.7215(2) 0.97063(13) 0.15155(8) 0.0193(4) Uani 1 1 d . . . N4 N 0.4826(3) 1.03996(15) 0.12693(9) 0.0156(5) Uani 1 1 d . . . N1 N 0.5240(3) 0.77943(16) 0.12375(10) 0.0179(5) Uani 1 1 d . . . N2 N 0.2250(3) 0.89273(15) 0.10220(9) 0.0158(5) Uani 1 1 d . . . H2 H 0.1875 0.9515 0.0952 0.019 Uiso 1 1 calc R . . F5 F 0.8865(3) 0.52302(14) 0.17005(10) 0.0452(6) Uani 1 1 d . . . N3 N 0.4331(3) 0.88943(16) 0.22051(9) 0.0178(5) Uani 1 1 d . . . C14 C 0.6503(3) 1.04486(17) 0.14001(11) 0.0157(5) Uani 1 1 d . . . F6 F 1.2447(3) 0.62070(14) 0.17498(10) 0.0428(5) Uani 1 1 d . . . C18 C 0.7389(3) 1.13247(18) 0.14049(11) 0.0161(5) Uani 1 1 d . . . F4 F 1.1233(3) 0.51809(16) 0.22812(10) 0.0501(6) Uani 1 1 d . . . C17 C 0.6428(3) 1.20961(17) 0.12217(10) 0.0152(5) Uani 1 1 d . . . C21 C 0.8966(4) 1.30075(19) 0.13787(11) 0.0199(6) Uani 1 1 d . . . H21 H 0.9520 1.3576 0.1371 0.024 Uiso 1 1 calc R . . F2 F 1.1388(3) 0.49133(14) 0.13772(10) 0.0481(6) Uani 1 1 d . . . C25 C 0.3794(4) 1.27688(19) 0.08697(12) 0.0214(6) Uani 1 1 d . . . H25 H 0.2631 1.2715 0.0755 0.026 Uiso 1 1 calc R . . C2 C 0.2990(4) 0.75326(19) 0.05050(12) 0.0208(6) Uani 1 1 d . . . H2A H 0.2033 0.7170 0.0620 0.025 Uiso 1 1 calc R . . H2B H 0.3193 0.7333 0.0125 0.025 Uiso 1 1 calc R . . C8 C 0.6092(4) 0.7443(2) 0.22172(13) 0.0254(6) Uani 1 1 d . . . H8A H 0.5055 0.7075 0.2215 0.030 Uiso 1 1 calc R . . H8B H 0.6976 0.7128 0.2455 0.030 Uiso 1 1 calc R . . C22 C 0.7241(3) 1.29484(18) 0.12011(11) 0.0168(5) Uani 1 1 d . . . C16 C 0.4690(3) 1.20165(18) 0.10559(11) 0.0171(5) Uani 1 1 d . . . C23 C 0.6263(4) 1.37073(19) 0.10115(12) 0.0221(6) Uani 1 1 d . . . H23 H 0.6781 1.4285 0.0999 0.026 Uiso 1 1 calc R . . C15 C 0.3854(3) 1.11200(17) 0.10837(11) 0.0160(5) Uani 1 1 d . . . F3 F 1.0073(3) 0.62527(17) 0.11750(9) 0.0494(6) Uani 1 1 d . . . C19 C 0.9070(3) 1.14017(19) 0.15699(11) 0.0188(5) Uani 1 1 d . . . H19 H 0.9701 1.0882 0.1689 0.023 Uiso 1 1 calc R . . C10 C 0.0688(4) 0.8531(2) 0.01133(13) 0.0283(7) Uani 1 1 d . . . H10A H 0.0279 0.9156 0.0078 0.042 Uiso 1 1 calc R . . H10B H -0.0126 0.8164 0.0297 0.042 Uiso 1 1 calc R . . H10C H 0.0826 0.8283 -0.0257 0.042 Uiso 1 1 calc R . . C6 C 0.2707(4) 0.8433(2) 0.22888(12) 0.0234(6) Uani 1 1 d . . . H6A H 0.2512 0.8462 0.2688 0.028 Uiso 1 1 calc R . . H6B H 0.2811 0.7787 0.2189 0.028 Uiso 1 1 calc R . . C3 C 0.2390(4) 0.85171(19) 0.04598(11) 0.0190(6) Uani 1 1 d . . . C12 C 0.5062(4) 0.6289(2) 0.07965(14) 0.0300(7) Uani 1 1 d . . . H12A H 0.6058 0.6157 0.1048 0.045 Uiso 1 1 calc R . . H12B H 0.5333 0.6204 0.0411 0.045 Uiso 1 1 calc R . . H12C H 0.4148 0.5879 0.0877 0.045 Uiso 1 1 calc R . . C1 C 0.4518(4) 0.72581(19) 0.08786(12) 0.0199(6) Uani 1 1 d . . . C24 C 0.4594(4) 1.36218(19) 0.08475(13) 0.0242(6) Uani 1 1 d . . . H24 H 0.3966 1.4137 0.0718 0.029 Uiso 1 1 calc R . . C5 C 0.1172(3) 0.8826(2) 0.19543(12) 0.0206(6) Uani 1 1 d . . . H5A H 0.0150 0.8655 0.2137 0.025 Uiso 1 1 calc R . . H5B H 0.1254 0.9495 0.1961 0.025 Uiso 1 1 calc R . . C20 C 0.9855(4) 1.22542(19) 0.15624(12) 0.0199(6) Uani 1 1 d . . . H20 H 1.1011 1.2309 0.1686 0.024 Uiso 1 1 calc R . . C4 C 0.0969(3) 0.85157(19) 0.13555(12) 0.0203(6) Uani 1 1 d . . . H4A H 0.1070 0.7848 0.1342 0.024 Uiso 1 1 calc R . . H4B H -0.0166 0.8682 0.1192 0.024 Uiso 1 1 calc R . . C7 C 0.5760(4) 0.8359(2) 0.24786(12) 0.0225(6) Uani 1 1 d . . . H7A H 0.5538 0.8258 0.2871 0.027 Uiso 1 1 calc R . . H7B H 0.6796 0.8727 0.2477 0.027 Uiso 1 1 calc R . . C9 C 0.6639(3) 0.74806(19) 0.16260(13) 0.0218(6) Uani 1 1 d . . . H9A H 0.7606 0.7898 0.1612 0.026 Uiso 1 1 calc R . . H9B H 0.7003 0.6871 0.1514 0.026 Uiso 1 1 calc R . . C26 C 0.0143(6) 0.4163(3) 0.01344(17) 0.0504(11) Uani 1 1 d . . . H26A H 0.1061 0.3724 0.0193 0.076 Uiso 1 1 calc R . . H26B H -0.0665 0.3950 -0.0164 0.076 Uiso 1 1 calc R . . H26C H -0.0423 0.4230 0.0478 0.076 Uiso 1 1 calc R . . C27 C 0.0851(8) 0.5070(5) -0.0026(2) 0.0300(14) Uani 0.50 1 d P . . O3 O 0.2348(6) 0.5112(4) -0.0046(2) 0.0382(11) Uani 0.50 1 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 C13 0.0305(16) 0.0234(15) 0.0202(14) -0.0041(12) 0.0052(12) -0.0032(12) C11 0.0351(17) 0.0232(15) 0.0162(13) 0.0003(11) 0.0064(12) -0.0033(12) Ni1 0.01462(18) 0.00961(17) 0.01571(18) 0.00047(12) 0.00164(12) -0.00098(12) P1 0.0223(4) 0.0128(3) 0.0213(4) -0.0004(3) 0.0031(3) -0.0031(3) O2 0.0168(10) 0.0182(10) 0.0316(12) 0.0013(8) -0.0010(8) -0.0010(7) F1 0.0361(11) 0.0344(11) 0.0411(11) -0.0118(9) -0.0020(9) 0.0118(9) O1 0.0206(10) 0.0130(9) 0.0243(10) 0.0018(8) 0.0021(8) 0.0009(7) N4 0.0164(11) 0.0108(10) 0.0197(11) 0.0013(8) 0.0013(9) -0.0010(8) N1 0.0165(11) 0.0145(11) 0.0229(12) 0.0010(9) 0.0040(9) 0.0007(9) N2 0.0197(11) 0.0108(10) 0.0172(11) 0.0010(8) 0.0032(9) -0.0010(8) F5 0.0293(11) 0.0334(11) 0.0738(16) -0.0047(11) 0.0095(10) -0.0097(9) N3 0.0193(12) 0.0175(11) 0.0163(11) 0.0004(9) 0.0002(9) -0.0021(9) C14 0.0221(13) 0.0121(12) 0.0132(12) -0.0006(10) 0.0026(10) 0.0001(10) F6 0.0302(11) 0.0332(11) 0.0651(15) -0.0101(10) 0.0054(10) -0.0101(9) C18 0.0193(13) 0.0136(12) 0.0156(12) -0.0012(10) 0.0028(10) -0.0020(10) F4 0.0535(14) 0.0506(14) 0.0467(13) 0.0244(11) 0.0070(11) 0.0177(11) C17 0.0217(13) 0.0128(12) 0.0113(11) -0.0004(9) 0.0038(10) 0.0000(10) C21 0.0262(15) 0.0150(13) 0.0191(13) -0.0021(11) 0.0063(11) -0.0069(11) F2 0.0477(13) 0.0331(11) 0.0666(15) -0.0255(11) 0.0239(11) -0.0066(10) C25 0.0204(14) 0.0187(14) 0.0250(14) -0.0002(11) -0.0005(11) 0.0010(11) C2 0.0252(14) 0.0171(13) 0.0201(13) -0.0048(11) 0.0021(11) -0.0048(11) C8 0.0249(15) 0.0189(14) 0.0310(16) 0.0055(12) -0.0060(12) -0.0003(11) C22 0.0243(14) 0.0131(12) 0.0137(12) -0.0007(10) 0.0065(10) -0.0012(10) C16 0.0214(14) 0.0119(12) 0.0180(13) -0.0006(10) 0.0030(10) -0.0008(10) C23 0.0324(16) 0.0132(13) 0.0213(14) 0.0002(11) 0.0064(12) -0.0013(11) C15 0.0198(13) 0.0126(12) 0.0159(12) -0.0009(10) 0.0034(10) 0.0003(10) F3 0.0654(16) 0.0501(14) 0.0312(11) 0.0136(10) -0.0049(10) -0.0069(11) C19 0.0205(14) 0.0172(13) 0.0189(13) 0.0001(11) 0.0022(11) -0.0007(11) C10 0.0319(17) 0.0255(16) 0.0263(16) 0.0007(13) -0.0056(13) -0.0010(13) C6 0.0224(15) 0.0268(15) 0.0213(14) 0.0046(12) 0.0037(11) -0.0049(12) C3 0.0237(14) 0.0165(13) 0.0166(13) -0.0002(10) -0.0007(11) -0.0029(11) C12 0.0343(17) 0.0187(15) 0.0373(18) -0.0066(13) 0.0041(14) 0.0014(13) C1 0.0216(14) 0.0152(13) 0.0233(14) -0.0003(11) 0.0048(11) 0.0004(10) C24 0.0297(16) 0.0141(13) 0.0290(16) 0.0045(12) 0.0041(12) 0.0046(11) C5 0.0170(13) 0.0217(14) 0.0240(14) 0.0007(11) 0.0065(11) -0.0026(10) C20 0.0185(13) 0.0230(14) 0.0184(13) -0.0019(11) 0.0027(10) -0.0055(11) C4 0.0157(13) 0.0198(14) 0.0254(14) 0.0009(11) 0.0014(11) -0.0028(10) C7 0.0234(15) 0.0227(15) 0.0206(14) 0.0032(11) -0.0028(11) -0.0018(11) C9 0.0156(13) 0.0172(13) 0.0319(15) -0.0005(12) -0.0014(11) 0.0020(10) C26 0.061(3) 0.055(3) 0.034(2) -0.0030(18) -0.0027(18) -0.017(2) C27 0.033(4) 0.042(4) 0.014(3) 0.001(3) -0.003(2) -0.006(3) O3 0.032(3) 0.047(3) 0.035(3) 0.009(2) 0.002(2) -0.004(2) _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 C13 N3 1.494(4) . ? C11 C3 1.536(4) . ? Ni1 N1 1.983(2) . ? Ni1 N4 1.994(2) . ? Ni1 N2 2.030(2) . ? Ni1 N3 2.039(2) . ? Ni1 O1 2.271(2) . ? P1 F4 1.575(2) . ? P1 F2 1.592(2) . ? P1 F6 1.595(2) . ? P1 F1 1.594(2) . ? P1 F5 1.600(2) . ? P1 F3 1.605(2) . ? O2 C15 1.232(3) . ? O1 C14 1.256(3) . ? N4 C14 1.352(3) . ? N4 C15 1.371(3) . ? N1 C1 1.277(4) . ? N1 C9 1.475(3) . ? N2 C4 1.481(3) . ? N2 C3 1.500(3) . ? N3 C6 1.492(4) . ? N3 C7 1.497(4) . ? C14 C18 1.474(4) . ? C18 C19 1.373(4) . ? C18 C17 1.424(4) . ? C17 C22 1.419(4) . ? C17 C16 1.417(4) . ? C21 C20 1.374(4) . ? C21 C22 1.411(4) . ? C25 C16 1.378(4) . ? C25 C24 1.415(4) . ? C2 C1 1.513(4) . ? C2 C3 1.533(4) . ? C8 C7 1.525(4) . ? C8 C9 1.527(4) . ? C22 C23 1.421(4) . ? C16 C15 1.487(4) . ? C23 C24 1.365(4) . ? C19 C20 1.407(4) . ? C10 C3 1.537(4) . ? C6 C5 1.527(4) . ? C12 C1 1.514(4) . ? C5 C4 1.514(4) . ? C26 C27 1.515(8) . ? C27 O3 1.201(8) . ? C27 C27 1.388(13) 3_565 ? C27 C26 1.396(8) 3_565 ? 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 152.74(10) . . ? N1 Ni1 N2 93.64(9) . . ? N4 Ni1 N2 97.23(9) . . ? N1 Ni1 N3 95.76(9) . . ? N4 Ni1 N3 105.88(9) . . ? N2 Ni1 N3 103.23(9) . . ? N1 Ni1 O1 100.58(8) . . ? N4 Ni1 O1 61.80(8) . . ? N2 Ni1 O1 155.64(8) . . ? N3 Ni1 O1 94.96(8) . . ? F4 P1 F2 89.65(14) . . ? F4 P1 F6 90.66(13) . . ? F2 P1 F6 89.79(12) . . ? F4 P1 F1 91.11(12) . . ? F2 P1 F1 179.15(13) . . ? F6 P1 F1 89.80(11) . . ? F4 P1 F5 90.86(13) . . ? F2 P1 F5 90.36(12) . . ? F6 P1 F5 178.47(14) . . ? F1 P1 F5 90.03(12) . . ? F4 P1 F3 179.40(14) . . ? F2 P1 F3 90.72(14) . . ? F6 P1 F3 89.81(13) . . ? F1 P1 F3 88.53(12) . . ? F5 P1 F3 88.67(13) . . ? C14 O1 Ni1 86.58(16) . . ? C14 N4 C15 123.9(2) . . ? C14 N4 Ni1 96.33(16) . . ? C15 N4 Ni1 139.50(18) . . ? C1 N1 C9 121.0(2) . . ? C1 N1 Ni1 127.08(19) . . ? C9 N1 Ni1 111.87(18) . . ? C4 N2 C3 115.5(2) . . ? C4 N2 Ni1 118.04(17) . . ? C3 N2 Ni1 107.12(16) . . ? C13 N3 C6 109.1(2) . . ? C13 N3 C7 106.0(2) . . ? C6 N3 C7 109.7(2) . . ? C13 N3 Ni1 110.13(17) . . ? C6 N3 Ni1 110.98(17) . . ? C7 N3 Ni1 110.80(17) . . ? O1 C14 N4 115.3(2) . . ? O1 C14 C18 123.8(2) . . ? N4 C14 C18 120.9(2) . . ? C19 C18 C17 120.9(2) . . ? C19 C18 C14 122.1(2) . . ? C17 C18 C14 117.0(2) . . ? C22 C17 C16 120.2(2) . . ? C22 C17 C18 119.0(2) . . ? C16 C17 C18 120.8(2) . . ? C20 C21 C22 120.9(3) . . ? C16 C25 C24 120.5(3) . . ? C1 C2 C3 121.9(2) . . ? C7 C8 C9 115.3(2) . . ? C21 C22 C17 118.8(2) . . ? C21 C22 C23 123.1(3) . . ? C17 C22 C23 118.1(3) . . ? C25 C16 C17 119.7(2) . . ? C25 C16 C15 120.7(2) . . ? C17 C16 C15 119.6(2) . . ? C24 C23 C22 121.2(3) . . ? O2 C15 N4 120.5(2) . . ? O2 C15 C16 122.0(2) . . ? N4 C15 C16 117.5(2) . . ? C18 C19 C20 119.7(3) . . ? N3 C6 C5 115.1(2) . . ? N2 C3 C11 106.8(2) . . ? N2 C3 C2 111.4(2) . . ? C11 C3 C2 110.6(2) . . ? N2 C3 C10 111.2(2) . . ? C11 C3 C10 108.9(2) . . ? C2 C3 C10 108.0(2) . . ? N1 C1 C2 122.5(2) . . ? N1 C1 C12 123.9(3) . . ? C2 C1 C12 113.6(2) . . ? C23 C24 C25 120.3(3) . . ? C4 C5 C6 114.2(2) . . ? C21 C20 C19 120.7(3) . . ? N2 C4 C5 111.7(2) . . ? N3 C7 C8 115.9(2) . . ? N1 C9 C8 110.4(2) . . ? O3 C27 C27 173.8(9) . 3_565 ? O3 C27 C26 120.1(6) . 3_565 ? C27 C27 C26 65.9(6) 3_565 3_565 ? O3 C27 C26 116.6(6) . . ? C27 C27 C26 57.3(5) 3_565 . ? C26 C27 C26 123.2(5) 3_565 . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 0.50 _diffrn_measured_fraction_theta_full 0.000 _refine_diff_density_max 0.833 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.087