#Supplementary Material (ESI) for Dalton Transactions #This journal is (c) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Luigi Fabbrizzi' _publ_contact_author_name 'Luigi Fabbrizzi' _publ_contact_author_address ; Luigi Fabbrizzi Dipartimento di Chimica Generale Universita di Pavia via Taramelli 12 27100 Pavia (Italy) ; _publ_contact_author_email 'fabbrizz@unipv.it' _publ_section_title ; A Novel Fluorescence Redox Switch Based on the Formal NiII/NiI Couple ; data_licc5 _database_code_CSD 162666 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H33 Cl2 Cu N5 O8' _chemical_formula_weight 702.03 _chemical_melting_point ? _chemical_compound_source 'synthesis as described' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Cu' 'Cu' 0.3201 1.2651 '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' 'C' 'C' 0.0033 0.0016 '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' 'O' 'O' 0.0106 0.0060 '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 'P 21/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 19.472(3) _cell_length_b 7.613(2) _cell_length_c 21.797(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.793(15) _cell_angle_gamma 90.00 _cell_volume 3020.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.35 _cell_measurement_theta_max 12.11 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.529999 _exptl_crystal_size_mid 0.419999 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method none _exptl_crystal_F_000 1452 _exptl_absorpt_coefficient_mu 0.958 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 345 _diffrn_standards_interval_time 300 _diffrn_standards_decay_% 73 _diffrn_reflns_number 6072 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0625 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.99 _reflns_number_total 5911 _reflns_number_gt 3654 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1992)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1992)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR92 (Altomare et al, 1993)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1997)' _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^)+(0.0731P)^2^+7.9532P] 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 5910 _refine_ls_number_parameters 445 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.1241 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_all 0.1880 _refine_ls_wR_factor_gt 0.1560 _refine_ls_goodness_of_fit_all 1.033 _refine_ls_goodness_of_fit_gt 1.114 _refine_ls_restrained_S_all 1.055 _refine_ls_restrained_S_obs 1.146 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/su_max 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 0.95555(3) 0.06787(9) 0.20600(3) 0.0416(2) Uani 1 d . . N1 N 0.8704(2) 0.2291(6) 0.1606(2) 0.0472(11) Uani 1 d . . N2 N 1.0286(2) 0.1648(6) 0.1699(2) 0.0459(11) Uani 1 d . . N3 N 1.0447(2) 0.0131(6) 0.2765(2) 0.0437(10) Uani 1 d . . N4 N 0.9158(2) -0.0519(6) 0.2675(2) 0.0463(11) Uani 1 d . . N5 N 0.9190(3) -0.1451(7) 0.1292(3) 0.0623(14) Uani 1 d . . C1 C 0.8688(3) 0.2703(9) 0.0926(3) 0.058(2) Uani 1 d . . H1A H 0.8586(3) 0.1624(9) 0.0673(3) 0.070 Uiso 1 calc R . H1B H 0.8282(3) 0.3500(9) 0.0721(3) 0.070 Uiso 1 calc R . C2 C 0.9373(4) 0.3503(9) 0.0878(3) 0.062(2) Uani 1 d . . H2A H 0.9505(4) 0.4504(9) 0.1173(3) 0.074 Uiso 1 calc R . H2B H 0.9253(4) 0.3952(9) 0.0436(3) 0.074 Uiso 1 calc R . C3 C 1.0046(3) 0.2353(9) 0.1030(3) 0.058(2) Uani 1 d . . H3A H 0.9937(3) 0.1386(9) 0.0720(3) 0.069 Uiso 1 calc R . H3B H 1.0442(3) 0.3033(9) 0.0976(3) 0.069 Uiso 1 calc R . C4 C 1.0958(3) 0.1547(8) 0.2078(3) 0.0495(14) Uani 1 d . . C5 C 1.1073(3) 0.0742(8) 0.2722(3) 0.0477(13) Uani 1 d . . C6 C 1.1714(4) 0.0593(9) 0.3258(3) 0.068(2) Uani 1 d . . H6 H 1.2159(4) 0.0976(9) 0.3238(3) 0.081 Uiso 1 calc R . C7 C 1.1680(4) -0.0135(11) 0.3825(3) 0.079(2) Uani 1 d . . H7 H 1.2107(4) -0.0238(11) 0.4191(3) 0.095 Uiso 1 calc R . C8 C 1.1025(4) -0.0715(9) 0.3860(3) 0.068(2) Uani 1 d . . H8 H 1.1006(4) -0.1205(9) 0.4244(3) 0.081 Uiso 1 calc R . C9 C 1.0399(3) -0.0549(8) 0.3309(3) 0.0496(14) Uani 1 d . . C10 C 0.9632(3) -0.1009(7) 0.3226(3) 0.0500(14) Uani 1 d . . C11 C 0.8362(3) -0.0885(9) 0.2474(3) 0.061(2) Uani 1 d . . H11A H 0.8246(3) -0.1215(9) 0.2856(3) 0.074 Uiso 1 calc R . H11B H 0.8234(3) -0.1862(9) 0.2168(3) 0.074 Uiso 1 calc R . C12 C 0.7912(3) 0.0718(10) 0.2152(3) 0.065(2) Uani 1 d . . H12A H 0.7398(3) 0.0445(10) 0.2055(3) 0.078 Uiso 1 calc R . H12B H 0.8040(3) 0.1667(10) 0.2469(3) 0.078 Uiso 1 calc R . C13 C 0.7995(3) 0.1382(10) 0.1529(3) 0.062(2) Uani 1 d . . H13A H 0.7940(3) 0.0394(10) 0.1235(3) 0.074 Uiso 1 calc R . H13B H 0.7596(3) 0.2191(10) 0.1319(3) 0.074 Uiso 1 calc R . C14 C 0.8755(3) 0.3986(8) 0.1985(3) 0.056(2) Uani 1 d . . H14A H 0.8752(3) 0.4967(8) 0.1700(3) 0.067 Uiso 1 calc R . H14B H 0.8322(3) 0.4089(8) 0.2105(3) 0.067 Uiso 1 calc R . C15 C 0.9429(4) 0.4119(9) 0.2599(3) 0.067(2) Uani 1 d . . C16 C 0.9401(6) 0.3481(11) 0.3188(4) 0.098(3) Uani 1 d . . H16 H 0.8948(6) 0.3028(11) 0.3162(4) 0.118 Uiso 1 calc R . C17 C 0.9963(8) 0.3409(13) 0.3833(8) 0.149(6) Uani 1 d . . H17 H 0.9914(8) 0.3021(13) 0.4220(8) 0.179 Uiso 1 calc R . C18 C 1.0535(5) 0.3986(10) 0.3759(4) 0.077(2) Uani 1 d . . C19 C 1.1218(7) 0.3875(18) 0.4466(8) 0.189(9) Uani 1 d . . H19 H 1.1160(7) 0.3462(18) 0.4846(8) 0.227 Uiso 1 calc R . C20 C 1.1846(8) 0.4410(20) 0.4452(8) 0.162(7) Uani 1 d . . H20 H 1.2267(8) 0.4326(20) 0.4825(8) 0.195 Uiso 1 calc R . C21 C 1.1884(8) 0.5104(21) 0.3878(9) 0.187(9) Uani 1 d . . H21 H 1.2348(8) 0.5511(21) 0.3916(9) 0.224 Uiso 1 calc R . C22 C 1.1289(9) 0.5326(13) 0.3181(7) 0.159(6) Uani 1 d . . H22 H 1.1334(9) 0.5776(13) 0.2800(7) 0.191 Uiso 1 calc R . C23 C 1.0720(5) 0.4719(10) 0.3275(5) 0.093(3) Uani 1 d . . C24 C 1.0050(4) 0.4841(11) 0.2580(4) 0.086(3) Uani 1 d . . H24 H 1.0090(4) 0.5355(11) 0.2207(4) 0.103 Uiso 1 calc R . C25 C 1.1612(3) 0.2192(10) 0.1925(4) 0.073(2) Uani 1 d . . H25A H 1.2053(4) 0.1697(53) 0.2234(16) 0.109 Uiso 1 calc R . H25B H 1.1636(16) 0.3450(11) 0.1956(24) 0.109 Uiso 1 calc R . H25C H 1.1564(14) 0.1838(57) 0.1489(10) 0.109 Uiso 1 calc R . C26 C 0.9482(4) -0.1924(10) 0.3774(3) 0.072(2) Uani 1 d . . H26A H 0.9419(28) -0.1067(10) 0.4073(14) 0.108 Uiso 1 calc R . H26B H 0.9889(13) -0.2676(52) 0.4003(16) 0.108 Uiso 1 calc R . H26C H 0.9043(16) -0.2615(53) 0.3598(4) 0.108 Uiso 1 calc R . C27 C 0.9006(3) -0.1868(8) 0.0757(3) 0.0541(15) Uani 1 d . . C28 C 0.8773(5) -0.2346(11) 0.0073(3) 0.079(2) Uani 1 d . . H28A H 0.8346(19) -0.3081(60) -0.0037(7) 0.119 Uiso 1 calc R . H28B H 0.9161(12) -0.2973(64) -0.0006(6) 0.119 Uiso 1 calc R . H28C H 0.8658(29) -0.1304(11) -0.0192(3) 0.119 Uiso 1 calc R . Cl1 Cl 0.81267(8) 0.1515(3) 0.42375(7) 0.0636(5) Uani 1 d . . O1 O 0.8845(3) 0.1533(15) 0.4609(3) 0.154(4) Uani 1 d . . O2 O 0.8140(9) 0.3292(19) 0.4013(9) 0.180(7) Uani 0.60 d P . O2A O 0.8166(12) -0.0316(19) 0.4437(11) 0.145(8) Uani 0.40 d P . O3 O 0.7916(4) 0.0905(16) 0.3626(3) 0.177(4) Uani 1 d . . O4 O 0.7630(4) 0.1710(16) 0.4530(4) 0.180(4) Uani 1 d . . Cl2 Cl 0.38180(9) 0.2305(2) 0.39363(8) 0.0631(4) Uani 1 d D . O5 O 0.3350(10) 0.1680(31) 0.4236(11) 0.120(7) Uani 0.40 d PDU . O5A O 0.3964(11) 0.3803(14) 0.4262(7) 0.238(14) Uani 0.60 d PD . O6 O 0.3340(10) 0.2757(39) 0.3347(8) 0.154(14) Uani 0.40 d PD . O6A O 0.4486(6) 0.1630(26) 0.4073(12) 0.257(11) Uani 0.60 d PDU . O7 O 0.4151(14) 0.3643(31) 0.4307(9) 0.205(11) Uani 0.40 d PDU . O7A O 0.3545(12) 0.2622(24) 0.3285(5) 0.183(9) Uani 0.60 d PDU . O8 O 0.4256(14) 0.1174(31) 0.3756(18) 0.269(13) Uani 0.40 d PDU . O8A O 0.3517(9) 0.0852(14) 0.4134(8) 0.109(6) Uani 0.60 d PDU . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0383(3) 0.0462(4) 0.0380(3) 0.0027(3) 0.0109(2) 0.0030(3) N1 0.042(2) 0.048(3) 0.045(2) -0.002(2) 0.008(2) 0.005(2) N2 0.050(3) 0.045(3) 0.043(2) 0.003(2) 0.017(2) 0.002(2) N3 0.046(2) 0.042(3) 0.039(2) -0.001(2) 0.012(2) 0.008(2) N4 0.050(3) 0.043(3) 0.048(3) -0.005(2) 0.021(2) 0.000(2) N5 0.068(3) 0.059(3) 0.062(3) -0.015(3) 0.025(3) -0.004(3) C1 0.062(4) 0.057(4) 0.045(3) 0.009(3) 0.005(3) 0.014(3) C2 0.078(4) 0.056(4) 0.047(3) 0.013(3) 0.019(3) 0.010(4) C3 0.069(4) 0.059(4) 0.050(3) 0.005(3) 0.027(3) -0.005(3) C4 0.047(3) 0.044(3) 0.058(3) -0.005(3) 0.020(3) -0.001(3) C5 0.040(3) 0.045(3) 0.052(3) -0.004(3) 0.008(2) 0.008(3) C6 0.049(3) 0.065(4) 0.076(4) -0.004(4) 0.007(3) 0.006(3) C7 0.060(4) 0.088(6) 0.060(4) 0.000(4) -0.013(3) 0.023(4) C8 0.084(5) 0.064(4) 0.044(3) 0.002(3) 0.009(3) 0.019(4) C9 0.061(3) 0.044(3) 0.041(3) -0.001(3) 0.014(2) 0.012(3) C10 0.072(4) 0.037(3) 0.046(3) -0.002(2) 0.027(3) 0.009(3) C11 0.056(3) 0.068(4) 0.067(4) -0.009(3) 0.030(3) -0.011(3) C12 0.048(3) 0.071(5) 0.079(4) -0.005(4) 0.025(3) -0.002(3) C13 0.039(3) 0.069(4) 0.068(4) -0.011(3) 0.006(3) 0.006(3) C14 0.060(4) 0.047(4) 0.056(3) -0.003(3) 0.015(3) 0.009(3) C15 0.069(4) 0.055(4) 0.057(4) -0.013(3) 0.000(3) 0.016(4) C16 0.142(8) 0.058(5) 0.055(4) -0.021(4) -0.014(5) 0.034(5) C17 0.225(14) 0.063(6) 0.249(16) -0.036(8) 0.194(14) -0.021(8) C18 0.124(7) 0.053(5) 0.074(5) -0.003(4) 0.059(5) 0.014(4) C19 0.096(8) 0.137(11) 0.246(17) -0.111(12) -0.047(10) 0.027(8) C20 0.116(10) 0.141(12) 0.150(12) -0.055(10) -0.051(9) 0.033(9) C21 0.139(12) 0.141(12) 0.172(13) -0.084(11) -0.078(11) 0.040(10) C22 0.295(19) 0.067(7) 0.212(14) -0.030(7) 0.209(15) -0.021(9) C23 0.087(6) 0.048(5) 0.174(9) -0.038(5) 0.084(6) -0.009(4) C24 0.070(5) 0.074(5) 0.094(6) -0.043(5) 0.004(4) 0.013(4) C25 0.055(4) 0.078(5) 0.092(5) -0.004(4) 0.036(4) -0.008(4) C26 0.102(6) 0.064(5) 0.064(4) 0.010(3) 0.045(4) 0.016(4) C27 0.066(4) 0.043(4) 0.056(4) 0.000(3) 0.024(3) 0.000(3) C28 0.109(6) 0.075(5) 0.056(4) -0.002(4) 0.031(4) -0.001(5) Cl1 0.0536(9) 0.0886(13) 0.0451(8) -0.0067(8) 0.0134(6) 0.0109(8) O1 0.079(4) 0.298(12) 0.080(4) -0.008(6) 0.021(3) -0.037(6) O2 0.206(16) 0.107(10) 0.223(17) 0.074(11) 0.071(13) 0.056(10) O2A 0.184(19) 0.040(9) 0.194(20) 0.029(10) 0.045(16) -0.001(10) O3 0.118(6) 0.317(14) 0.089(5) -0.087(7) 0.029(4) -0.036(7) O4 0.122(6) 0.303(13) 0.155(7) -0.053(8) 0.097(6) -0.007(7) Cl2 0.0542(9) 0.0553(10) 0.0766(11) 0.0001(8) 0.0192(8) -0.0016(8) O5 0.059(9) 0.171(18) 0.117(16) 0.020(17) 0.018(9) -0.043(14) O5A 0.527(40) 0.042(7) 0.129(16) -0.020(8) 0.097(19) 0.047(14) O6 0.070(10) 0.199(29) 0.150(22) 0.102(20) -0.014(11) -0.027(13) O6A 0.056(7) 0.221(20) 0.484(31) -0.037(24) 0.083(13) 0.031(11) O7 0.259(25) 0.247(17) 0.095(17) -0.062(17) 0.044(16) -0.227(17) O7A 0.368(24) 0.133(14) 0.051(7) -0.031(8) 0.081(10) -0.095(16) O8 0.245(30) 0.075(14) 0.511(30) -0.102(21) 0.163(34) 0.026(21) O8A 0.158(15) 0.070(8) 0.090(8) 0.016(6) 0.031(8) -0.044(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.911(4) . ? Cu1 N4 1.990(5) . ? Cu1 N2 1.995(4) . ? Cu1 N1 2.017(4) . ? Cu1 N5 2.256(5) . ? N1 C13 1.499(8) . ? N1 C1 1.504(7) . ? N1 C14 1.517(7) . ? N2 C4 1.278(7) . ? N2 C3 1.465(7) . ? N3 C9 1.327(7) . ? N3 C5 1.339(7) . ? N4 C10 1.283(7) . ? N4 C11 1.480(7) . ? N5 C27 1.137(7) . ? C1 C2 1.503(9) . ? C1 H1A 0.97 . ? C1 H1B 0.97 . ? C2 C3 1.512(9) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 H3A 0.97 . ? C3 H3B 0.97 . ? C4 C5 1.475(8) . ? C4 C25 1.508(8) . ? C5 C6 1.378(8) . ? C6 C7 1.376(10) . ? C6 H6 0.93 . ? C7 C8 1.376(10) . ? C7 H7 0.93 . ? C8 C9 1.381(8) . ? C8 H8 0.93 . ? C9 C10 1.481(8) . ? C10 C26 1.499(8) . ? C11 C12 1.520(9) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 C13 1.510(9) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 C15 1.508(8) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C15 C24 1.342(11) . ? C15 C16 1.393(11) . ? C16 C17 1.44(2) . ? C16 H16 0.93 . ? C17 C18 1.259(12) . ? C17 H17 0.93 . ? C18 C23 1.351(12) . ? C18 C19 1.64(2) . ? C19 C20 1.30(2) . ? C19 H19 0.93 . ? C20 C21 1.38(2) . ? C20 H20 0.93 . ? C21 C22 1.56(2) . ? C21 H21 0.93 . ? C22 C23 1.282(13) . ? C22 H22 0.93 . ? C23 C24 1.614(12) . ? C24 H24 0.93 . ? C25 H25A 0.96 . ? C25 H25B 0.96 . ? C25 H25C 0.96 . ? C26 H26A 0.96 . ? C26 H26B 0.96 . ? C26 H26C 0.96 . ? C27 C28 1.443(9) . ? C28 H28A 0.96 . ? C28 H28B 0.96 . ? C28 H28C 0.96 . ? Cl1 O3 1.332(6) . ? Cl1 O4 1.342(6) . ? Cl1 O1 1.345(6) . ? Cl1 O2 1.442(13) . ? Cl1 O2A 1.454(14) . ? Cl2 O7 1.319(12) . ? Cl2 O5A 1.320(10) . ? Cl2 O6A 1.329(10) . ? Cl2 O6 1.337(12) . ? Cl2 O7A 1.350(10) . ? Cl2 O8 1.365(14) . ? Cl2 O5 1.381(14) . ? Cl2 O8A 1.390(9) . ? O5 O8A 0.78(3) . ? O6A O8 0.76(4) . ? O6A O7 1.81(3) . ? O7A O8 1.78(4) . ? 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 N3 Cu1 N4 79.5(2) . . ? N3 Cu1 N2 80.0(2) . . ? N4 Cu1 N2 159.6(2) . . ? N3 Cu1 N1 151.8(2) . . ? N4 Cu1 N1 99.3(2) . . ? N2 Cu1 N1 99.1(2) . . ? N3 Cu1 N5 113.4(2) . . ? N4 Cu1 N5 94.2(2) . . ? N2 Cu1 N5 93.1(2) . . ? N1 Cu1 N5 94.9(2) . . ? C13 N1 C1 106.8(4) . . ? C13 N1 C14 109.4(5) . . ? C1 N1 C14 109.5(5) . . ? C13 N1 Cu1 109.8(4) . . ? C1 N1 Cu1 109.7(3) . . ? C14 N1 Cu1 111.5(3) . . ? C4 N2 C3 123.8(5) . . ? C4 N2 Cu1 115.6(4) . . ? C3 N2 Cu1 120.5(4) . . ? C9 N3 C5 123.5(5) . . ? C9 N3 Cu1 118.1(4) . . ? C5 N3 Cu1 117.3(4) . . ? C10 N4 C11 123.5(5) . . ? C10 N4 Cu1 116.1(4) . . ? C11 N4 Cu1 120.3(4) . . ? C27 N5 Cu1 149.6(5) . . ? C2 C1 N1 116.4(5) . . ? C2 C1 H1A 108.2(4) . . ? N1 C1 H1A 108.2(3) . . ? C2 C1 H1B 108.2(3) . . ? N1 C1 H1B 108.2(3) . . ? H1A C1 H1B 107.4 . . ? C1 C2 C3 118.1(5) . . ? C1 C2 H2A 107.8(4) . . ? C3 C2 H2A 107.8(4) . . ? C1 C2 H2B 107.8(3) . . ? C3 C2 H2B 107.8(3) . . ? H2A C2 H2B 107.1 . . ? N2 C3 C2 112.0(5) . . ? N2 C3 H3A 109.2(3) . . ? C2 C3 H3A 109.2(4) . . ? N2 C3 H3B 109.2(3) . . ? C2 C3 H3B 109.2(3) . . ? H3A C3 H3B 107.9 . . ? N2 C4 C5 114.6(5) . . ? N2 C4 C25 126.1(6) . . ? C5 C4 C25 119.3(5) . . ? N3 C5 C6 119.0(6) . . ? N3 C5 C4 112.0(4) . . ? C6 C5 C4 128.9(6) . . ? C7 C6 C5 118.5(6) . . ? C7 C6 H6 120.8(4) . . ? C5 C6 H6 120.8(4) . . ? C6 C7 C8 121.3(6) . . ? C6 C7 H7 119.3(4) . . ? C8 C7 H7 119.3(4) . . ? C7 C8 C9 118.2(6) . . ? C7 C8 H8 120.9(4) . . ? C9 C8 H8 120.9(4) . . ? N3 C9 C8 119.5(6) . . ? N3 C9 C10 111.8(5) . . ? C8 C9 C10 128.7(6) . . ? N4 C10 C9 113.9(5) . . ? N4 C10 C26 127.0(6) . . ? C9 C10 C26 119.1(5) . . ? N4 C11 C12 110.9(5) . . ? N4 C11 H11A 109.5(3) . . ? C12 C11 H11A 109.5(3) . . ? N4 C11 H11B 109.5(3) . . ? C12 C11 H11B 109.5(4) . . ? H11A C11 H11B 108.0 . . ? C13 C12 C11 117.1(5) . . ? C13 C12 H12A 108.0(3) . . ? C11 C12 H12A 108.0(3) . . ? C13 C12 H12B 108.0(4) . . ? C11 C12 H12B 108.0(4) . . ? H12A C12 H12B 107.3 . . ? N1 C13 C12 116.3(5) . . ? N1 C13 H13A 108.2(3) . . ? C12 C13 H13A 108.2(4) . . ? N1 C13 H13B 108.2(3) . . ? C12 C13 H13B 108.2(3) . . ? H13A C13 H13B 107.4 . . ? C15 C14 N1 114.1(5) . . ? C15 C14 H14A 108.7(4) . . ? N1 C14 H14A 108.7(3) . . ? C15 C14 H14B 108.7(4) . . ? N1 C14 H14B 108.7(3) . . ? H14A C14 H14B 107.6 . . ? C24 C15 C16 120.1(7) . . ? C24 C15 C14 120.7(7) . . ? C16 C15 C14 119.2(7) . . ? C15 C16 C17 130.4(10) . . ? C15 C16 H16 114.8(5) . . ? C17 C16 H16 114.8(6) . . ? C18 C17 C16 105.1(11) . . ? C18 C17 H17 127.4(8) . . ? C16 C17 H17 127.4(6) . . ? C17 C18 C23 137.5(11) . . ? C17 C18 C19 108.7(12) . . ? C23 C18 C19 113.7(11) . . ? C20 C19 C18 114.7(17) . . ? C20 C19 H19 122.6(12) . . ? C18 C19 H19 122.6(8) . . ? C19 C20 C21 119.6(13) . . ? C19 C20 H20 120.2(12) . . ? C21 C20 H20 120.2(9) . . ? C20 C21 C22 131.5(16) . . ? C20 C21 H21 114.3(9) . . ? C22 C21 H21 114.3(10) . . ? C23 C22 C21 100.9(12) . . ? C23 C22 H22 129.5(9) . . ? C21 C22 H22 129.5(10) . . ? C22 C23 C18 139.4(13) . . ? C22 C23 C24 106.6(11) . . ? C18 C23 C24 113.9(8) . . ? C15 C24 C23 112.7(8) . . ? C15 C24 H24 123.7(5) . . ? C23 C24 H24 123.7(5) . . ? C4 C25 H25A 109.5(4) . . ? C4 C25 H25B 109.5(4) . . ? H25A C25 H25B 109.5 . . ? C4 C25 H25C 109.5(4) . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C10 C26 H26A 109.5(3) . . ? C10 C26 H26B 109.5(4) . . ? H26A C26 H26B 109.5 . . ? C10 C26 H26C 109.5(4) . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N5 C27 C28 178.4(7) . . ? C27 C28 H28A 109.5(4) . . ? C27 C28 H28B 109.5(4) . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5(4) . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O3 Cl1 O4 119.7(5) . . ? O3 Cl1 O1 119.4(5) . . ? O4 Cl1 O1 119.0(5) . . ? O3 Cl1 O2 91.4(9) . . ? O4 Cl1 O2 99.2(8) . . ? O1 Cl1 O2 93.1(8) . . ? O3 Cl1 O2A 86.0(10) . . ? O4 Cl1 O2A 86.2(10) . . ? O1 Cl1 O2A 84.1(9) . . ? O2 Cl1 O2A 174.6(11) . . ? O7 Cl2 O5A 15.9(18) . . ? O7 Cl2 O6A 86.1(16) . . ? O5A Cl2 O6A 101.9(11) . . ? O7 Cl2 O6 114.4(17) . . ? O5A Cl2 O6 103.7(14) . . ? O6A Cl2 O6 127.4(14) . . ? O7 Cl2 O7A 115.5(13) . . ? O5A Cl2 O7A 109.9(10) . . ? O6A Cl2 O7A 107.1(13) . . ? O6 Cl2 O7A 20.5(17) . . ? O7 Cl2 O8 116.2(16) . . ? O5A Cl2 O8 131.5(16) . . ? O6A Cl2 O8 32.8(18) . . ? O6 Cl2 O8 100.3(16) . . ? O7A Cl2 O8 82.1(19) . . ? O7 Cl2 O5 103.9(13) . . ? O5A Cl2 O5 95.5(11) . . ? O6A Cl2 O5 121.2(13) . . ? O6 Cl2 O5 101.0(11) . . ? O7A Cl2 O5 118.7(14) . . ? O8 Cl2 O5 120.3(16) . . ? O7 Cl2 O8A 126.5(11) . . ? O5A Cl2 O8A 123.7(10) . . ? O6A Cl2 O8A 96.3(10) . . ? O6 Cl2 O8A 106.0(15) . . ? O7A Cl2 O8A 114.6(10) . . ? O8 Cl2 O8A 87.9(14) . . ? O5 Cl2 O8A 32.6(12) . . ? O8A O5 Cl2 74.4(15) . . ? O8 O6A Cl2 76.2(16) . . ? O8 O6A O7 119.3(22) . . ? Cl2 O6A O7 46.7(8) . . ? Cl2 O7 O6A 47.2(10) . . ? Cl2 O7A O8 49.3(11) . . ? O6A O8 Cl2 71.0(15) . . ? O6A O8 O7A 109.0(23) . . ? Cl2 O8 O7A 48.6(10) . . ? O5 O8A Cl2 73.1(13) . . ? _refine_diff_density_max 0.827 _refine_diff_density_min -0.733 _refine_diff_density_rms 0.084 #===END data_licc11ac _database_code_CSD 162667 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H30 F12 N4 Ni1 P2' _chemical_formula_sum 'C26 H30 F12 N4 Ni P2' _chemical_formula_weight 747.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Ni' 'Ni' 0.3393 1.1124 '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' 'C' 'C' 0.0033 0.0016 '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' 'F' 'F' 0.0171 0.0103 '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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.922(5) _cell_length_b 18.364(10) _cell_length_c 11.729(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.91(6) _cell_angle_gamma 90.00 _cell_volume 1458.8(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5 _cell_measurement_theta_max 10 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.878 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 240 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6074 _diffrn_reflns_av_R_equivalents 0.1620 _diffrn_reflns_av_sigmaI/netI 0.4562 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4374 _reflns_number_gt 915 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR92 (Altomare et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1998)' _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. The crystal structure is almost centrosymmetric (91%) and could be described in space group P21/m rather than in the chiral space group P21. In that case, the two alternative positions for the naphthalene system cannot be refined even with the use of geometrical constraints. Structural refinement of 114 parameters in space group P21/m would yield a final _refine_ls_R_factor_gt of about 14% and chemically unacceptable bond distances and angles for the naphthalene rings. ; _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^)+(0.1081P)^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 0.02(8) _refine_ls_number_reflns 4374 _refine_ls_number_parameters 198 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.2961 _refine_ls_R_factor_gt 0.1020 _refine_ls_wR_factor_ref 0.3160 _refine_ls_wR_factor_gt 0.2292 _refine_ls_goodness_of_fit_ref 0.844 _refine_ls_restrained_S_all 0.845 _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 Ni1 Ni 0.0537(3) 0.3022(3) 0.18453(16) 0.0299(6) Uani 1 1 d . . . N1 N -0.0699(17) 0.2974(13) 0.0249(11) 0.033(3) Uiso 1 1 d . . . N2 N 0.085(3) 0.2082(12) 0.2089(19) 0.036(5) Uiso 1 1 d . . . N4 N 0.084(3) 0.4092(12) 0.201(2) 0.041(6) Uiso 1 1 d . . . C1 C -0.001(4) 0.2449(14) -0.045(3) 0.054(8) Uiso 1 1 d . . . H1A H 0.1360 0.2547 -0.0466 0.064 Uiso 1 1 calc R . . H1B H -0.0776 0.2474 -0.1236 0.064 Uiso 1 1 calc R . . C2 C -0.021(4) 0.1630(15) 0.009(2) 0.053(8) Uiso 1 1 d . . . H2A H -0.1577 0.1554 0.0134 0.064 Uiso 1 1 calc R . . H2B H 0.0117 0.1277 -0.0452 0.064 Uiso 1 1 calc R . . C3 C 0.094(4) 0.1480(16) 0.118(3) 0.046(7) Uiso 1 1 d . . . H3A H 0.2305 0.1418 0.1109 0.055 Uiso 1 1 calc R . . H3B H 0.0509 0.1024 0.1464 0.055 Uiso 1 1 calc R . . C4 C 0.115(2) 0.1803(9) 0.3196(15) 0.030(3) Uiso 1 1 d . . . N3 N 0.1133(16) 0.3009(12) 0.3422(10) 0.027(3) Uiso 1 1 d D . . C5 C 0.123(5) 0.2407(15) 0.404(2) 0.061(10) Uiso 1 1 d D . . C6 C 0.088(3) 0.2397(12) 0.5222(19) 0.043(6) Uiso 1 1 d D . . H6 H 0.0577 0.1976 0.5590 0.051 Uiso 1 1 calc R . . C7 C 0.104(2) 0.3088(14) 0.5750(15) 0.049(5) Uiso 1 1 d D . . H7 H 0.0956 0.3132 0.6529 0.058 Uiso 1 1 calc R . . C8 C 0.133(3) 0.3721(12) 0.5106(17) 0.040(6) Uiso 1 1 d D . . H8 H 0.1661 0.4167 0.5467 0.048 Uiso 1 1 calc R . . C9 C 0.108(3) 0.3639(12) 0.3937(18) 0.033(6) Uiso 1 1 d D . . C10 C 0.114(6) 0.424(3) 0.308(4) 0.105(13) Uiso 1 1 d . . . C11 C 0.102(5) 0.459(2) 0.111(3) 0.072(11) Uiso 1 1 d . . . H11A H 0.2268 0.4509 0.0874 0.086 Uiso 1 1 calc R . . H11B H 0.0999 0.5083 0.1393 0.086 Uiso 1 1 calc R . . C12 C -0.075(4) 0.4460(15) 0.005(2) 0.051(7) Uiso 1 1 d . . . H12A H -0.1995 0.4472 0.0302 0.061 Uiso 1 1 calc R . . H12B H -0.0763 0.4835 -0.0536 0.061 Uiso 1 1 calc R . . C13 C -0.041(3) 0.3709(12) -0.045(2) 0.038(6) Uiso 1 1 d . . . H13A H 0.0926 0.3704 -0.0578 0.046 Uiso 1 1 calc R . . H13B H -0.1285 0.3675 -0.1208 0.046 Uiso 1 1 calc R . . C14 C -0.304(2) 0.303(2) 0.0171(15) 0.049(4) Uiso 1 1 d . . . H14A H -0.3571 0.3445 -0.0294 0.059 Uiso 1 1 calc R . . H14B H -0.3680 0.2592 -0.0199 0.059 Uiso 1 1 calc R . . C24 C -0.369(3) 0.2494(11) 0.2042(15) 0.046(6) Uiso 1 1 d D . . H24 H -0.3803 0.2032 0.1711 0.055 Uiso 1 1 calc R . . C15 C -0.343(2) 0.3098(10) 0.1379(14) 0.048(5) Uiso 1 1 d D . . C16 C -0.359(3) 0.3789(11) 0.1841(16) 0.045(6) Uiso 1 1 d D . . H16 H -0.3420 0.4197 0.1400 0.054 Uiso 1 1 calc R . . C17 C -0.398(3) 0.3885(9) 0.2944(14) 0.041(5) Uiso 1 1 d D . . H17 H -0.4311 0.4342 0.3191 0.049 Uiso 1 1 calc R . . C18 C -0.388(2) 0.3284(7) 0.3665(14) 0.029(4) Uiso 1 1 d D . . C23 C -0.380(3) 0.2588(9) 0.3205(15) 0.041(5) Uiso 1 1 d D . . C22 C -0.376(5) 0.1985(14) 0.392(2) 0.103(11) Uiso 1 1 d D . . H22 H -0.3712 0.1526 0.3591 0.124 Uiso 1 1 calc R . . C21 C -0.379(4) 0.2034(12) 0.510(2) 0.080(8) Uiso 1 1 d D . . H21 H -0.3735 0.1643 0.5607 0.096 Uiso 1 1 calc R . . C20 C -0.392(3) 0.2761(11) 0.539(2) 0.061(7) Uiso 1 1 d D . . H20 H -0.3818 0.2824 0.6187 0.073 Uiso 1 1 calc R . . C19 C -0.415(6) 0.3417(14) 0.4799(18) 0.131(15) Uiso 1 1 d D . . H19 H -0.4428 0.3864 0.5099 0.157 Uiso 1 1 calc R . . C25 C 0.179(3) 0.1060(13) 0.360(2) 0.044(6) Uiso 1 1 d . . . H25A H 0.0840 0.0849 0.3993 0.065 Uiso 1 1 calc R . . H25B H 0.3051 0.1087 0.4129 0.065 Uiso 1 1 calc R . . H25C H 0.1906 0.0764 0.2944 0.065 Uiso 1 1 calc R . . C26 C 0.128(3) 0.5036(13) 0.358(2) 0.044(7) Uiso 1 1 d . . . H26A H 0.0804 0.5043 0.4291 0.066 Uiso 1 1 calc R . . H26B H 0.0498 0.5357 0.3023 0.066 Uiso 1 1 calc R . . H26C H 0.2634 0.5194 0.3730 0.066 Uiso 1 1 calc R . . P1 P 0.3810(12) 0.1241(5) -0.2025(6) 0.0419(19) Uani 1 1 d . . . P2 P 0.3798(16) 0.4872(4) -0.2090(9) 0.061(3) Uani 1 1 d . . . F1 F 0.415(2) 0.1477(10) -0.0743(16) 0.065(5) Uiso 1 1 d . . . F2 F 0.198(4) 0.4328(15) -0.233(2) 0.140(9) Uiso 1 1 d . . . F3 F 0.573(3) 0.5350(11) -0.1643(16) 0.096(6) Uiso 1 1 d . . . F4 F 0.3724(19) 0.1032(8) -0.3368(12) 0.050(4) Uiso 1 1 d . . . F5 F 0.318(2) 0.5203(9) -0.3299(15) 0.075(5) Uiso 1 1 d . . . F6 F 0.2635(18) 0.5518(8) -0.1712(11) 0.062(4) Uiso 1 1 d . . . F7 F 0.499(3) 0.4218(13) -0.2407(19) 0.115(7) Uiso 1 1 d . . . F8 F 0.403(3) 0.4525(14) -0.081(2) 0.117(9) Uiso 1 1 d . . . F9 F 0.422(3) 0.2024(14) -0.245(2) 0.130(8) Uiso 1 1 d . . . F10 F 0.612(3) 0.1090(13) -0.195(2) 0.125(7) Uiso 1 1 d . . . F11 F 0.411(5) 0.040(2) -0.176(3) 0.216(13) Uiso 1 1 d . . . F12 F 0.162(2) 0.1525(9) -0.2325(14) 0.067(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 Ni1 0.0358(11) 0.0293(11) 0.0249(10) 0.0022(17) 0.0069(8) 0.0246(15) P1 0.048(4) 0.053(5) 0.016(3) -0.001(3) -0.014(3) 0.011(4) P2 0.094(7) 0.027(4) 0.058(6) 0.002(4) 0.005(5) -0.007(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 N2 1.76(2) . ? Ni1 N3 1.810(11) . ? Ni1 N1 1.893(12) . ? Ni1 N4 1.98(2) . ? N1 C1 1.41(3) . ? N1 C14 1.606(19) . ? N1 C13 1.61(3) . ? N2 C4 1.37(3) . ? N2 C3 1.54(3) . ? N4 C10 1.26(5) . ? N4 C11 1.41(4) . ? C1 C2 1.65(4) . ? C2 C3 1.39(4) . ? C4 C5 1.48(3) . ? C4 C25 1.48(3) . ? N3 C9 1.31(2) . ? N3 C5 1.32(2) . ? C5 C6 1.46(2) . ? C6 C7 1.41(2) . ? C7 C8 1.42(2) . ? C8 C9 1.35(2) . ? C9 C10 1.51(5) . ? C10 C26 1.56(5) . ? C11 C12 1.58(4) . ? C12 C13 1.53(3) . ? C14 C15 1.50(2) . ? C24 C15 1.388(10) . ? C24 C23 1.391(10) . ? C15 C16 1.393(10) . ? C16 C17 1.388(10) . ? C17 C18 1.384(10) . ? C18 C23 1.395(10) . ? C18 C19 1.400(10) . ? C23 C22 1.384(10) . ? C22 C21 1.393(10) . ? C21 C20 1.387(10) . ? C20 C19 1.382(10) . ? P1 F1 1.53(2) . ? P1 F9 1.57(3) . ? P1 F12 1.572(17) . ? P1 F11 1.58(4) . ? P1 F10 1.60(2) . ? P1 F4 1.611(15) . ? P2 F5 1.520(18) . ? P2 F7 1.55(2) . ? P2 F6 1.549(16) . ? P2 F2 1.58(3) . ? P2 F3 1.59(2) . ? P2 F8 1.61(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 N2 Ni1 N3 80.0(11) . . ? N2 Ni1 N1 97.5(10) . . ? N3 Ni1 N1 166.2(5) . . ? N2 Ni1 N4 162.1(6) . . ? N3 Ni1 N4 85.2(10) . . ? N1 Ni1 N4 99.2(9) . . ? C1 N1 C14 118(2) . . ? C1 N1 C13 100.9(12) . . ? C14 N1 C13 98.6(19) . . ? C1 N1 Ni1 117.8(16) . . ? C14 N1 Ni1 107.3(9) . . ? C13 N1 Ni1 112.7(14) . . ? C4 N2 C3 111.4(19) . . ? C4 N2 Ni1 120.7(16) . . ? C3 N2 Ni1 127.8(18) . . ? C10 N4 C11 125(3) . . ? C10 N4 Ni1 108(3) . . ? C11 N4 Ni1 126(2) . . ? N1 C1 C2 110(2) . . ? C3 C2 C1 117(2) . . ? C2 C3 N2 113(3) . . ? N2 C4 C5 109.3(17) . . ? N2 C4 C25 128.5(18) . . ? C5 C4 C25 120.6(19) . . ? C9 N3 C5 119.6(14) . . ? C9 N3 Ni1 116.0(15) . . ? C5 N3 Ni1 123.2(17) . . ? N3 C5 C6 122(2) . . ? N3 C5 C4 106(2) . . ? C6 C5 C4 129(2) . . ? C7 C6 C5 113(2) . . ? C6 C7 C8 120.7(16) . . ? C9 C8 C7 116(2) . . ? N3 C9 C8 124(2) . . ? N3 C9 C10 110(2) . . ? C8 C9 C10 125(3) . . ? N4 C10 C9 119(4) . . ? N4 C10 C26 124(4) . . ? C9 C10 C26 116(3) . . ? N4 C11 C12 109(3) . . ? C13 C12 C11 106(2) . . ? C12 C13 N1 121(2) . . ? C15 C14 N1 109.0(12) . . ? C15 C24 C23 119.3(19) . . ? C24 C15 C16 118.7(18) . . ? C24 C15 C14 122(2) . . ? C16 C15 C14 119(2) . . ? C17 C16 C15 122(2) . . ? C18 C17 C16 118.3(19) . . ? C17 C18 C23 119.7(17) . . ? C17 C18 C19 116.2(16) . . ? C23 C18 C19 123.5(17) . . ? C22 C23 C24 119.6(19) . . ? C22 C23 C18 119.8(19) . . ? C24 C23 C18 120.6(18) . . ? C23 C22 C21 123(3) . . ? C20 C21 C22 109(3) . . ? C19 C20 C21 136(3) . . ? C20 C19 C18 107(2) . . ? F1 P1 F9 93.0(12) . . ? F1 P1 F12 94.1(9) . . ? F9 P1 F12 81.6(11) . . ? F1 P1 F11 95.7(14) . . ? F9 P1 F11 159.0(15) . . ? F12 P1 F11 116.6(15) . . ? F1 P1 F10 92.4(11) . . ? F9 P1 F10 86.2(13) . . ? F12 P1 F10 166.4(12) . . ? F11 P1 F10 74.4(14) . . ? F1 P1 F4 172.9(10) . . ? F9 P1 F4 83.0(10) . . ? F12 P1 F4 91.2(8) . . ? F11 P1 F4 86.2(13) . . ? F10 P1 F4 81.4(10) . . ? F5 P2 F7 98.5(11) . . ? F5 P2 F6 84.1(9) . . ? F7 P2 F6 177.3(12) . . ? F5 P2 F2 91.5(12) . . ? F7 P2 F2 84.9(12) . . ? F6 P2 F2 95.4(12) . . ? F5 P2 F3 98.2(10) . . ? F7 P2 F3 93.1(12) . . ? F6 P2 F3 86.2(10) . . ? F2 P2 F3 170.3(14) . . ? F5 P2 F8 169.4(13) . . ? F7 P2 F8 87.9(13) . . ? F6 P2 F8 89.5(11) . . ? F2 P2 F8 80.7(14) . . ? F3 P2 F8 89.8(13) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.968 _refine_diff_density_min -0.887 _refine_diff_density_rms 0.158