# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'M. Dolores Santana' _publ_contact_author_email DSL@UM.ES _publ_section_title ; Luminescence of Five-coordinated Nickel(II) Complexes with Substituted-8-Hydroxyquinolines and Macrocyclic Ligands ; loop_ _publ_author_name 'M. Dolores Santana' 'Gabriel Garcia' 'Luis Garcia' 'Rocio Garcia-Bueno' 'Antonio Laguna' 'Miguel Monge' ; J.Perez ; # Attachment 'Pcrystaldata.cif' data_complex6a _database_code_depnum_ccdc_archive 'CCDC 746278' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H30 N5 Ni O, F6 P' _chemical_formula_sum 'C22 H30 F6 N5 Ni O P' _chemical_formula_weight 584.19 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' F F 0.0171 0.0103 '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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 15.8753(8) _cell_length_b 9.8776(5) _cell_length_c 15.9209(8) _cell_angle_alpha 90.00 _cell_angle_beta 99.7640(10) _cell_angle_gamma 90.00 _cell_volume 2460.4(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 lath _exptl_crystal_colour red _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.925 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8586 _exptl_absorpt_correction_T_max 0.9552 _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 27849 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.21 _reflns_number_total 5690 _reflns_number_gt 4959 _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^)+(0.0468P)^2^+2.6820P] 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 5690 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1087 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.42330(2) 0.12000(3) 0.14622(2) 0.01162(10) Uani 1 1 d . . . O1 O 0.44100(11) 0.25928(19) 0.06302(12) 0.0175(4) Uani 1 1 d . . . N2 N 0.39898(14) -0.0667(2) 0.19058(13) 0.0156(4) Uani 1 1 d . . . H2 H 0.3406 -0.0795 0.1733 0.019 Uiso 1 1 calc R . . N1 N 0.55186(14) 0.0800(2) 0.16881(13) 0.0145(4) Uani 1 1 d . . . N3 N 0.43474(14) 0.2301(2) 0.25492(14) 0.0162(5) Uani 1 1 d . . . H3 H 0.3829 0.2751 0.2524 0.019 Uiso 1 1 calc R . . N4 N 0.28890(14) 0.1692(2) 0.09229(13) 0.0141(4) Uani 1 1 d . . . N5 N 0.20065(16) -0.0713(3) 0.20893(17) 0.0287(6) Uani 1 1 d . . . C3 C 0.44069(17) -0.1667(3) 0.13977(16) 0.0164(5) Uani 1 1 d . . . C2 C 0.53810(18) -0.1662(3) 0.16625(18) 0.0189(6) Uani 1 1 d . . . H2A H 0.5511 -0.2121 0.2222 0.023 Uiso 1 1 calc R . . H2B H 0.5617 -0.2239 0.1250 0.023 Uiso 1 1 calc R . . C1 C 0.58784(16) -0.0357(3) 0.17380(16) 0.0159(5) Uani 1 1 d . . . C9 C 0.60305(17) 0.2060(3) 0.17852(17) 0.0181(5) Uani 1 1 d . . . H9A H 0.5863 0.2633 0.1274 0.022 Uiso 1 1 calc R . . H9B H 0.6643 0.1830 0.1825 0.022 Uiso 1 1 calc R . . C8 C 0.59057(17) 0.2854(3) 0.25735(18) 0.0215(6) Uani 1 1 d . . . H8A H 0.6302 0.3634 0.2636 0.026 Uiso 1 1 calc R . . H8B H 0.6071 0.2266 0.3078 0.026 Uiso 1 1 calc R . . C7 C 0.50046(19) 0.3382(3) 0.25799(19) 0.0220(6) Uani 1 1 d . . . H7A H 0.5007 0.3927 0.3102 0.026 Uiso 1 1 calc R . . H7B H 0.4841 0.3989 0.2084 0.026 Uiso 1 1 calc R . . C6 C 0.44690(18) 0.1523(3) 0.33584(17) 0.0208(6) Uani 1 1 d . . . H6A H 0.4372 0.2133 0.3826 0.025 Uiso 1 1 calc R . . H6B H 0.5068 0.1203 0.3487 0.025 Uiso 1 1 calc R . . C5 C 0.38766(19) 0.0317(3) 0.33316(17) 0.0230(6) Uani 1 1 d . . . H5A H 0.3294 0.0599 0.3067 0.028 Uiso 1 1 calc R . . H5B H 0.3853 0.0030 0.3923 0.028 Uiso 1 1 calc R . . C4 C 0.4140(2) -0.0892(3) 0.28415(18) 0.0253(6) Uani 1 1 d . . . H4A H 0.4755 -0.1079 0.3038 0.030 Uiso 1 1 calc R . . H4B H 0.3815 -0.1699 0.2970 0.030 Uiso 1 1 calc R . . C10 C 0.41485(19) -0.1267(3) 0.04604(17) 0.0214(6) Uani 1 1 d . . . H10A H 0.3524 -0.1274 0.0307 0.032 Uiso 1 1 calc R . . H10B H 0.4392 -0.1914 0.0101 0.032 Uiso 1 1 calc R . . H10C H 0.4364 -0.0357 0.0373 0.032 Uiso 1 1 calc R . . C11 C 0.4081(2) -0.3110(3) 0.1517(2) 0.0262(6) Uani 1 1 d . . . H11A H 0.3457 -0.3132 0.1352 0.039 Uiso 1 1 calc R . . H11B H 0.4237 -0.3376 0.2116 0.039 Uiso 1 1 calc R . . H11C H 0.4339 -0.3740 0.1159 0.039 Uiso 1 1 calc R . . C12 C 0.68377(18) -0.0580(3) 0.1897(2) 0.0259(6) Uani 1 1 d . . . H12A H 0.7130 0.0298 0.1941 0.039 Uiso 1 1 calc R . . H12B H 0.6999 -0.1096 0.1423 0.039 Uiso 1 1 calc R . . H12C H 0.7004 -0.1085 0.2429 0.039 Uiso 1 1 calc R . . C21 C 0.21208(17) 0.1239(3) 0.10302(17) 0.0174(5) Uani 1 1 d . . . C20 C 0.13367(17) 0.1766(3) 0.06181(17) 0.0192(6) Uani 1 1 d . . . H20 H 0.0811 0.1389 0.0714 0.023 Uiso 1 1 calc R . . C19 C 0.13499(17) 0.2831(3) 0.00790(17) 0.0202(6) Uani 1 1 d . . . H19 H 0.0828 0.3223 -0.0194 0.024 Uiso 1 1 calc R . . C18 C 0.21356(17) 0.3356(3) -0.00766(17) 0.0171(5) Uani 1 1 d . . . C17 C 0.22055(18) 0.4456(3) -0.06240(18) 0.0215(6) Uani 1 1 d . . . H17 H 0.1705 0.4886 -0.0917 0.026 Uiso 1 1 calc R . . C16 C 0.29928(19) 0.4901(3) -0.07327(18) 0.0228(6) Uani 1 1 d . . . H16 H 0.3031 0.5650 -0.1099 0.027 Uiso 1 1 calc R . . C15 C 0.37519(18) 0.4285(3) -0.03180(17) 0.0187(5) Uani 1 1 d . . . H15 H 0.4289 0.4617 -0.0415 0.022 Uiso 1 1 calc R . . C14 C 0.37252(16) 0.3194(3) 0.02326(16) 0.0145(5) Uani 1 1 d . . . C13 C 0.28973(16) 0.2732(3) 0.03638(16) 0.0140(5) Uani 1 1 d . . . C22 C 0.20732(17) 0.0140(3) 0.16236(18) 0.0204(6) Uani 1 1 d . . . P1 P 0.12392(4) 0.81846(8) 0.93326(5) 0.01929(16) Uani 1 1 d . . . F5 F 0.07217(11) 0.68140(18) 0.94148(11) 0.0287(4) Uani 1 1 d . . . F2 F 0.19610(12) 0.7703(2) 1.00977(12) 0.0401(5) Uani 1 1 d . . . F4 F 0.17373(12) 0.74931(19) 0.86540(12) 0.0323(4) Uani 1 1 d . . . F3 F 0.17470(13) 0.9569(2) 0.92653(14) 0.0432(5) Uani 1 1 d . . . F1 F 0.05065(12) 0.86738(19) 0.85780(11) 0.0337(4) Uani 1 1 d . . . F6 F 0.07281(12) 0.88831(19) 1.00096(12) 0.0316(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.00960(16) 0.01315(17) 0.01196(16) 0.00151(13) 0.00140(11) 0.00044(12) O1 0.0113(9) 0.0200(10) 0.0211(9) 0.0069(8) 0.0028(7) 0.0006(7) N2 0.0170(11) 0.0165(11) 0.0142(10) 0.0004(9) 0.0052(9) 0.0002(9) N1 0.0133(10) 0.0187(11) 0.0115(10) 0.0014(8) 0.0020(8) -0.0002(9) N3 0.0123(10) 0.0177(11) 0.0184(11) -0.0021(9) 0.0024(9) 0.0027(9) N4 0.0130(10) 0.0176(11) 0.0118(10) -0.0007(8) 0.0022(8) 0.0008(9) N5 0.0195(13) 0.0368(15) 0.0301(14) 0.0076(12) 0.0048(11) -0.0090(11) C3 0.0201(14) 0.0137(12) 0.0160(12) -0.0027(10) 0.0050(10) 0.0002(10) C2 0.0202(14) 0.0158(13) 0.0205(13) 0.0002(11) 0.0030(11) 0.0034(11) C1 0.0139(12) 0.0226(14) 0.0114(11) 0.0011(10) 0.0027(10) 0.0026(10) C9 0.0119(12) 0.0216(14) 0.0202(13) 0.0020(11) 0.0012(10) -0.0011(10) C8 0.0160(13) 0.0245(15) 0.0228(14) -0.0017(12) -0.0003(11) -0.0065(11) C7 0.0238(15) 0.0165(13) 0.0254(14) -0.0064(11) 0.0030(12) -0.0041(11) C6 0.0193(14) 0.0274(15) 0.0154(13) -0.0038(11) 0.0022(11) -0.0008(11) C5 0.0258(15) 0.0304(16) 0.0146(13) 0.0015(12) 0.0085(11) 0.0005(12) C4 0.0402(18) 0.0218(15) 0.0157(13) 0.0052(11) 0.0101(12) 0.0030(13) C10 0.0219(14) 0.0260(15) 0.0158(13) -0.0042(11) 0.0019(11) -0.0022(12) C11 0.0320(17) 0.0126(13) 0.0353(17) -0.0019(12) 0.0093(13) -0.0003(12) C12 0.0164(14) 0.0290(16) 0.0328(17) 0.0051(13) 0.0052(12) 0.0076(12) C21 0.0149(12) 0.0200(13) 0.0174(13) -0.0038(11) 0.0032(10) -0.0023(11) C20 0.0128(12) 0.0243(14) 0.0204(13) -0.0044(11) 0.0027(10) -0.0008(11) C19 0.0135(13) 0.0251(15) 0.0193(13) -0.0062(11) -0.0044(10) 0.0024(11) C18 0.0169(13) 0.0171(13) 0.0156(12) -0.0033(10) -0.0014(10) 0.0041(10) C17 0.0216(14) 0.0171(13) 0.0222(14) 0.0010(11) -0.0065(11) 0.0047(11) C16 0.0272(15) 0.0165(13) 0.0223(14) 0.0055(11) -0.0024(12) 0.0022(11) C15 0.0191(13) 0.0170(13) 0.0197(13) 0.0024(11) 0.0027(11) -0.0021(11) C14 0.0149(12) 0.0142(12) 0.0140(12) -0.0015(10) 0.0010(10) 0.0005(10) C13 0.0142(12) 0.0136(12) 0.0135(11) -0.0036(10) 0.0008(10) 0.0016(10) C22 0.0113(12) 0.0278(15) 0.0223(14) -0.0015(12) 0.0032(10) -0.0047(11) P1 0.0153(3) 0.0206(4) 0.0222(4) -0.0005(3) 0.0038(3) -0.0004(3) F5 0.0269(9) 0.0235(9) 0.0348(10) 0.0027(8) 0.0026(8) -0.0037(7) F2 0.0216(9) 0.0617(14) 0.0339(10) -0.0018(10) -0.0042(8) 0.0026(9) F4 0.0345(10) 0.0338(10) 0.0317(9) -0.0012(8) 0.0148(8) 0.0088(8) F3 0.0443(12) 0.0330(11) 0.0593(14) -0.0105(10) 0.0290(11) -0.0146(9) F1 0.0353(11) 0.0351(11) 0.0295(10) 0.0068(8) 0.0018(8) 0.0120(8) F6 0.0286(10) 0.0346(10) 0.0343(10) -0.0056(8) 0.0133(8) -0.0012(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 Ni1 O1 1.9628(18) . ? Ni1 N3 2.026(2) . ? Ni1 N2 2.035(2) . ? Ni1 N1 2.050(2) . ? Ni1 N4 2.215(2) . ? O1 C14 1.304(3) . ? N2 C4 1.485(3) . ? N2 C3 1.500(3) . ? N1 C1 1.274(3) . ? N1 C9 1.480(3) . ? N3 C6 1.484(3) . ? N3 C7 1.488(3) . ? N4 C21 1.337(3) . ? N4 C13 1.361(3) . ? N5 C22 1.139(4) . ? C3 C10 1.531(4) . ? C3 C2 1.532(4) . ? C3 C11 1.539(4) . ? C2 C1 1.506(4) . ? C1 C12 1.517(4) . ? C9 C8 1.521(4) . ? C8 C7 1.524(4) . ? C6 C5 1.515(4) . ? C5 C4 1.523(4) . ? C21 C20 1.405(4) . ? C21 C22 1.449(4) . ? C20 C19 1.360(4) . ? C19 C18 1.411(4) . ? C18 C17 1.409(4) . ? C18 C13 1.430(4) . ? C17 C16 1.363(4) . ? C16 C15 1.410(4) . ? C15 C14 1.394(4) . ? C14 C13 1.439(4) . ? P1 F4 1.5964(18) . ? P1 F2 1.597(2) . ? P1 F1 1.5986(19) . ? P1 F3 1.600(2) . ? P1 F5 1.6005(19) . ? P1 F6 1.6103(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ni1 N3 101.40(9) . . ? O1 Ni1 N2 157.93(8) . . ? N3 Ni1 N2 100.66(9) . . ? O1 Ni1 N1 90.07(8) . . ? N3 Ni1 N1 90.64(9) . . ? N2 Ni1 N1 90.36(9) . . ? O1 Ni1 N4 79.82(8) . . ? N3 Ni1 N4 98.87(8) . . ? N2 Ni1 N4 96.11(9) . . ? N1 Ni1 N4 167.27(8) . . ? C14 O1 Ni1 116.33(16) . . ? C4 N2 C3 115.6(2) . . ? C4 N2 Ni1 118.44(17) . . ? C3 N2 Ni1 106.42(15) . . ? C1 N1 C9 121.0(2) . . ? C1 N1 Ni1 127.32(19) . . ? C9 N1 Ni1 111.65(16) . . ? C6 N3 C7 110.8(2) . . ? C6 N3 Ni1 116.30(17) . . ? C7 N3 Ni1 111.97(16) . . ? C21 N4 C13 116.5(2) . . ? C21 N4 Ni1 135.78(18) . . ? C13 N4 Ni1 107.68(16) . . ? N2 C3 C10 106.6(2) . . ? N2 C3 C2 111.5(2) . . ? C10 C3 C2 111.0(2) . . ? N2 C3 C11 110.8(2) . . ? C10 C3 C11 108.6(2) . . ? C2 C3 C11 108.3(2) . . ? C1 C2 C3 121.0(2) . . ? N1 C1 C2 122.6(2) . . ? N1 C1 C12 124.6(3) . . ? C2 C1 C12 112.8(2) . . ? N1 C9 C8 111.9(2) . . ? C9 C8 C7 115.8(2) . . ? N3 C7 C8 114.1(2) . . ? N3 C6 C5 113.2(2) . . ? C6 C5 C4 114.1(2) . . ? N2 C4 C5 112.6(2) . . ? N4 C21 C20 124.8(3) . . ? N4 C21 C22 118.9(2) . . ? C20 C21 C22 116.2(2) . . ? C19 C20 C21 118.3(3) . . ? C20 C19 C18 120.3(3) . . ? C17 C18 C19 123.8(3) . . ? C17 C18 C13 119.1(3) . . ? C19 C18 C13 117.0(2) . . ? C16 C17 C18 119.8(3) . . ? C17 C16 C15 122.0(3) . . ? C14 C15 C16 120.9(3) . . ? O1 C14 C15 123.0(2) . . ? O1 C14 C13 119.5(2) . . ? C15 C14 C13 117.5(2) . . ? N4 C13 C18 123.0(2) . . ? N4 C13 C14 116.4(2) . . ? C18 C13 C14 120.6(2) . . ? N5 C22 C21 177.6(3) . . ? F4 P1 F2 90.86(11) . . ? F4 P1 F1 90.09(10) . . ? F2 P1 F1 179.03(11) . . ? F4 P1 F3 90.42(11) . . ? F2 P1 F3 90.06(12) . . ? F1 P1 F3 90.12(12) . . ? F4 P1 F5 90.77(10) . . ? F2 P1 F5 89.85(11) . . ? F1 P1 F5 89.95(10) . . ? F3 P1 F5 178.81(11) . . ? F4 P1 F6 179.41(11) . . ? F2 P1 F6 89.71(10) . . ? F1 P1 F6 89.34(10) . . ? F3 P1 F6 89.74(10) . . ? F5 P1 F6 89.07(10) . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 0.50 _diffrn_measured_fraction_theta_full 0.000 _refine_diff_density_max 0.647 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.088 #===END data_complex2b _database_code_depnum_ccdc_archive 'CCDC 746279' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H33 N4 Ni O, F6 P' _chemical_formula_sum 'C22 H33 F6 N4 Ni O P' _chemical_formula_weight 573.20 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 orthorhombic _symmetry_space_group_name_H-M PBN21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 8.4631(16) _cell_length_b 15.9967(11) _cell_length_c 18.1177(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2452.8(5) _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 dark _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.925 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8438 _exptl_absorpt_correction_T_max 0.9381 _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 26638 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0603 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.17 _reflns_number_total 5671 _reflns_number_gt 5090 _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^)+(0.0517P)^2^+2.6866P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.037(18) _refine_ls_number_reflns 5671 _refine_ls_number_parameters 316 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1274 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 C13 C 0.7185(7) 0.9761(4) 0.7798(3) 0.0340(13) Uani 1 1 d . . . H13A H 0.6346 0.9732 0.8169 0.051 Uiso 1 1 calc R . . H13B H 0.7103 1.0289 0.7527 0.051 Uiso 1 1 calc R . . H13C H 0.8217 0.9730 0.8042 0.051 Uiso 1 1 calc R . . C10 C 0.4861(6) 0.6702(3) 0.5562(4) 0.0350(13) Uani 1 1 d . . . H10A H 0.5111 0.6353 0.5991 0.053 Uiso 1 1 calc R . . H10B H 0.5704 0.6650 0.5195 0.053 Uiso 1 1 calc R . . H10C H 0.3857 0.6519 0.5346 0.053 Uiso 1 1 calc R . . Ni1 Ni 0.47405(6) 0.90682(3) 0.68403(3) 0.01660(13) Uani 1 1 d . . . O1 O 0.3285(4) 0.86492(19) 0.76084(17) 0.0190(7) Uani 1 1 d . . . C21 C 0.2595(6) 0.9236(3) 0.7992(3) 0.0166(10) Uani 1 1 d . . . C20 C 0.1505(6) 0.9092(3) 0.8557(3) 0.0231(10) Uani 1 1 d . . . H20 H 0.1228 0.8532 0.8675 0.028 Uiso 1 1 calc R . . N3 N 0.7021(5) 0.9055(2) 0.7278(2) 0.0238(9) Uani 1 1 d . . . N2 N 0.5195(5) 0.9510(2) 0.5794(2) 0.0187(8) Uani 1 1 d . . . H2 H 0.4953 1.0077 0.5803 0.022 Uiso 1 1 calc R . . N4 N 0.3927(4) 1.0226(2) 0.7243(2) 0.0158(8) Uani 1 1 d . . . N1 N 0.4966(4) 0.7872(2) 0.6455(2) 0.0204(8) Uani 1 1 d . . . C3 C 0.3975(6) 0.9108(3) 0.5307(3) 0.0218(10) Uani 1 1 d . . . C16 C 0.2700(6) 1.1573(3) 0.8034(3) 0.0212(10) Uani 1 1 d . . . H16 H 0.2319 1.2037 0.8307 0.025 Uiso 1 1 calc R . . C12 C 0.2345(7) 0.9216(3) 0.5678(3) 0.0262(12) Uani 1 1 d . . . H12A H 0.2366 0.8961 0.6170 0.039 Uiso 1 1 calc R . . H12B H 0.1533 0.8944 0.5377 0.039 Uiso 1 1 calc R . . H12C H 0.2103 0.9813 0.5724 0.039 Uiso 1 1 calc R . . C17 C 0.2234(5) 1.0757(3) 0.8235(3) 0.0186(9) Uani 1 1 d . . . C15 C 0.3680(6) 1.1702(3) 0.7457(3) 0.0233(10) Uani 1 1 d . . . H15 H 0.3965 1.2254 0.7315 0.028 Uiso 1 1 calc R . . C9 C 0.5413(6) 0.7295(3) 0.7053(3) 0.0288(12) Uani 1 1 d . . . H9A H 0.5332 0.6712 0.6872 0.035 Uiso 1 1 calc R . . H9B H 0.4667 0.7361 0.7469 0.035 Uiso 1 1 calc R . . C4 C 0.6837(6) 0.9449(3) 0.5521(3) 0.0233(10) Uani 1 1 d . . . H4A H 0.6955 0.9794 0.5070 0.028 Uiso 1 1 calc R . . H4B H 0.7074 0.8862 0.5389 0.028 Uiso 1 1 calc R . . C14 C 0.4274(6) 1.1008(3) 0.7068(3) 0.0212(10) Uani 1 1 d . . . H14 H 0.4957 1.1106 0.6661 0.025 Uiso 1 1 calc R . . C22 C 0.2902(5) 1.0092(3) 0.7821(2) 0.0141(9) Uani 1 1 d . . . C19 C 0.0812(6) 0.9741(3) 0.8951(2) 0.0222(10) Uani 1 1 d . . . H19 H 0.0082 0.9613 0.9333 0.027 Uiso 1 1 calc R . . C1 C 0.4721(6) 0.7607(3) 0.5802(3) 0.0235(10) Uani 1 1 d . . . C7 C 0.7256(7) 0.8273(3) 0.7732(3) 0.0323(13) Uani 1 1 d . . . H7A H 0.6488 0.8281 0.8144 0.039 Uiso 1 1 calc R . . H7B H 0.8327 0.8291 0.7951 0.039 Uiso 1 1 calc R . . C2 C 0.4343(6) 0.8175(3) 0.5176(3) 0.0236(11) Uani 1 1 d . . . H2A H 0.3423 0.7932 0.4915 0.028 Uiso 1 1 calc R . . H2B H 0.5246 0.8149 0.4829 0.028 Uiso 1 1 calc R . . C11 C 0.3887(7) 0.9526(3) 0.4539(3) 0.0331(13) Uani 1 1 d . . . H11A H 0.3657 1.0123 0.4598 0.050 Uiso 1 1 calc R . . H11B H 0.3047 0.9263 0.4248 0.050 Uiso 1 1 calc R . . H11C H 0.4900 0.9458 0.4285 0.050 Uiso 1 1 calc R . . C8 C 0.7074(6) 0.7454(3) 0.7321(3) 0.0306(12) Uani 1 1 d . . . H8A H 0.7798 0.7453 0.6892 0.037 Uiso 1 1 calc R . . H8B H 0.7394 0.6990 0.7651 0.037 Uiso 1 1 calc R . . C5 C 0.7990(6) 0.9745(3) 0.6101(3) 0.0236(11) Uani 1 1 d . . . H5A H 0.7579 1.0267 0.6324 0.028 Uiso 1 1 calc R . . H5B H 0.9008 0.9879 0.5859 0.028 Uiso 1 1 calc R . . C18 C 0.1158(5) 1.0566(3) 0.8801(2) 0.0198(10) Uani 1 1 d . . . H18 H 0.0674 1.1001 0.9077 0.024 Uiso 1 1 calc R . . C6 C 0.8290(6) 0.9112(3) 0.6715(3) 0.0285(12) Uani 1 1 d . . . H6A H 0.8435 0.8554 0.6489 0.034 Uiso 1 1 calc R . . H6B H 0.9290 0.9261 0.6966 0.034 Uiso 1 1 calc R . . P1 P 0.47341(16) 0.79605(8) 1.00106(7) 0.0238(3) Uani 1 1 d . . . F5 F 0.4877(5) 0.7389(2) 1.0707(2) 0.0557(11) Uani 1 1 d . . . F2 F 0.4644(5) 0.8545(3) 0.9296(2) 0.0543(11) Uani 1 1 d . . . F3 F 0.6339(4) 0.8415(2) 1.0239(2) 0.0467(9) Uani 1 1 d . . . F6 F 0.3151(4) 0.7509(2) 0.9772(2) 0.0417(8) Uani 1 1 d . . . F1 F 0.3776(4) 0.8645(2) 1.04596(19) 0.0397(8) Uani 1 1 d . . . F4 F 0.5730(4) 0.7299(2) 0.9537(2) 0.0459(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C13 0.029(3) 0.037(3) 0.036(3) -0.017(3) -0.011(2) 0.007(2) C10 0.029(3) 0.020(3) 0.056(4) -0.010(3) -0.001(3) 0.004(2) Ni1 0.0192(3) 0.0118(2) 0.0188(2) 0.0000(3) 0.0048(3) 0.0012(2) O1 0.0271(18) 0.0089(15) 0.0211(16) 0.0013(13) 0.0060(14) 0.0014(13) C21 0.015(2) 0.018(2) 0.018(2) -0.0014(18) -0.0001(18) -0.0006(18) C20 0.027(3) 0.020(2) 0.022(2) 0.001(2) 0.0023(19) -0.001(2) N3 0.028(2) 0.022(2) 0.021(2) -0.0002(18) -0.0030(17) 0.0044(18) N2 0.025(2) 0.0070(17) 0.025(2) -0.0007(15) 0.0044(16) -0.0008(15) N4 0.0171(19) 0.0151(19) 0.0153(18) -0.0016(15) 0.0042(14) 0.0021(15) N1 0.013(2) 0.0154(19) 0.032(2) -0.0010(18) 0.0068(16) 0.0029(15) C3 0.027(3) 0.013(2) 0.026(2) -0.0083(19) -0.0020(19) 0.003(2) C16 0.023(3) 0.015(2) 0.026(2) -0.0049(19) -0.003(2) 0.0043(19) C12 0.022(3) 0.015(2) 0.042(3) -0.004(2) 0.000(2) 0.003(2) C17 0.018(2) 0.017(2) 0.021(2) -0.0003(18) -0.0048(18) 0.0038(17) C15 0.028(3) 0.014(2) 0.028(3) -0.0032(19) 0.000(2) 0.0005(19) C9 0.036(3) 0.017(2) 0.034(3) 0.0059(19) 0.011(2) 0.005(2) C4 0.029(3) 0.016(2) 0.025(3) -0.001(2) 0.006(2) 0.001(2) C14 0.023(2) 0.015(2) 0.025(2) 0.0061(18) 0.0044(17) 0.0000(18) C22 0.018(2) 0.013(2) 0.0107(19) -0.0019(16) -0.0002(16) 0.0030(17) C19 0.022(2) 0.030(3) 0.014(2) 0.000(2) -0.0005(18) -0.001(2) C1 0.017(2) 0.014(2) 0.039(3) -0.002(2) 0.003(2) 0.0006(19) C7 0.030(3) 0.036(3) 0.031(3) 0.012(2) -0.002(2) 0.006(2) C2 0.022(2) 0.021(3) 0.028(3) -0.008(2) 0.0026(19) -0.0020(19) C11 0.048(3) 0.026(3) 0.025(3) 0.003(2) -0.004(3) 0.002(3) C8 0.036(3) 0.022(3) 0.034(3) 0.013(2) 0.007(2) 0.011(2) C5 0.014(2) 0.018(2) 0.039(3) 0.002(2) 0.005(2) -0.004(2) C18 0.020(2) 0.026(2) 0.013(2) -0.0034(19) -0.0009(18) 0.0061(19) C6 0.021(2) 0.026(2) 0.039(4) -0.001(2) 0.005(2) 0.005(2) P1 0.0226(6) 0.0156(6) 0.0331(7) -0.0035(5) -0.0043(6) 0.0002(5) F5 0.081(3) 0.045(2) 0.041(2) 0.0183(17) 0.0077(19) 0.010(2) F2 0.051(2) 0.059(3) 0.053(2) 0.023(2) -0.0117(19) -0.0043(19) F3 0.0338(19) 0.049(2) 0.057(2) -0.0026(18) -0.0132(16) -0.0046(16) F6 0.0314(18) 0.0360(18) 0.058(2) -0.0187(17) 0.0073(16) -0.0119(14) F1 0.0343(18) 0.0349(18) 0.050(2) -0.0231(16) -0.0058(16) 0.0085(14) F4 0.038(2) 0.052(2) 0.047(2) -0.0153(18) 0.0021(16) 0.0076(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C13 N3 1.477(6) . ? C10 C1 1.515(7) . ? Ni1 O1 1.976(3) . ? Ni1 N1 2.046(4) . ? Ni1 N2 2.059(4) . ? Ni1 N3 2.086(4) . ? Ni1 N4 2.106(4) . ? O1 C21 1.306(6) . ? C21 C20 1.397(7) . ? C21 C22 1.427(6) . ? C20 C19 1.390(7) . ? N3 C6 1.483(6) . ? N3 C7 1.510(6) . ? N2 C4 1.479(6) . ? N2 C3 1.503(6) . ? N4 C14 1.324(6) . ? N4 C22 1.377(5) . ? N1 C1 1.274(7) . ? N1 C9 1.472(6) . ? C3 C12 1.544(7) . ? C3 C2 1.544(6) . ? C3 C11 1.545(7) . ? C16 C15 1.350(7) . ? C16 C17 1.412(6) . ? C17 C18 1.404(7) . ? C17 C22 1.419(6) . ? C15 C14 1.407(6) . ? C9 C8 1.509(8) . ? C4 C5 1.511(7) . ? C19 C18 1.380(7) . ? C1 C2 1.488(7) . ? C7 C8 1.515(8) . ? C5 C6 1.525(7) . ? P1 F5 1.563(4) . ? P1 F6 1.582(3) . ? P1 F1 1.587(3) . ? P1 F3 1.595(4) . ? P1 F2 1.599(4) . ? P1 F4 1.602(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 O1 Ni1 N1 88.92(14) . . ? O1 Ni1 N2 151.79(15) . . ? N1 Ni1 N2 89.42(16) . . ? O1 Ni1 N3 107.80(15) . . ? N1 Ni1 N3 91.94(16) . . ? N2 Ni1 N3 100.40(16) . . ? O1 Ni1 N4 81.41(13) . . ? N1 Ni1 N4 166.20(15) . . ? N2 Ni1 N4 94.46(15) . . ? N3 Ni1 N4 100.35(15) . . ? C21 O1 Ni1 114.2(3) . . ? O1 C21 C20 124.5(4) . . ? O1 C21 C22 119.5(4) . . ? C20 C21 C22 116.0(4) . . ? C19 C20 C21 122.1(5) . . ? C13 N3 C6 108.8(4) . . ? C13 N3 C7 105.8(4) . . ? C6 N3 C7 109.3(4) . . ? C13 N3 Ni1 108.8(3) . . ? C6 N3 Ni1 114.1(3) . . ? C7 N3 Ni1 109.7(3) . . ? C4 N2 C3 114.9(4) . . ? C4 N2 Ni1 117.4(3) . . ? C3 N2 Ni1 105.4(3) . . ? C14 N4 C22 118.0(4) . . ? C14 N4 Ni1 132.5(3) . . ? C22 N4 Ni1 109.4(3) . . ? C1 N1 C9 121.0(4) . . ? C1 N1 Ni1 127.8(3) . . ? C9 N1 Ni1 111.1(3) . . ? N2 C3 C12 108.0(4) . . ? N2 C3 C2 111.4(4) . . ? C12 C3 C2 110.8(4) . . ? N2 C3 C11 112.1(4) . . ? C12 C3 C11 107.5(4) . . ? C2 C3 C11 106.9(4) . . ? C15 C16 C17 120.9(4) . . ? C18 C17 C16 124.8(4) . . ? C18 C17 C22 118.8(4) . . ? C16 C17 C22 116.4(4) . . ? C16 C15 C14 119.1(4) . . ? N1 C9 C8 111.8(4) . . ? N2 C4 C5 110.7(4) . . ? N4 C14 C15 123.1(4) . . ? N4 C22 C17 122.5(4) . . ? N4 C22 C21 115.4(4) . . ? C17 C22 C21 122.1(4) . . ? C18 C19 C20 121.6(4) . . ? N1 C1 C2 122.7(4) . . ? N1 C1 C10 124.9(5) . . ? C2 C1 C10 112.4(5) . . ? N3 C7 C8 115.8(4) . . ? C1 C2 C3 121.1(4) . . ? C9 C8 C7 113.5(4) . . ? C4 C5 C6 114.0(4) . . ? C19 C18 C17 119.3(4) . . ? N3 C6 C5 114.9(4) . . ? F5 P1 F6 91.0(2) . . ? F5 P1 F1 91.7(2) . . ? F6 P1 F1 91.27(17) . . ? F5 P1 F3 89.5(2) . . ? F6 P1 F3 179.2(2) . . ? F1 P1 F3 89.25(19) . . ? F5 P1 F2 178.3(2) . . ? F6 P1 F2 90.3(2) . . ? F1 P1 F2 89.3(2) . . ? F3 P1 F2 89.1(2) . . ? F5 P1 F4 90.3(2) . . ? F6 P1 F4 89.88(19) . . ? F1 P1 F4 177.7(2) . . ? F3 P1 F4 89.6(2) . . ? F2 P1 F4 88.7(2) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 0.50 _diffrn_measured_fraction_theta_full 0.000 _refine_diff_density_max 0.733 _refine_diff_density_min -0.897 _refine_diff_density_rms 0.094 #===END data_l2i2oxs _database_code_depnum_ccdc_archive 'CCDC 746280' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H31 I2 N4 Ni O, F6 P' _chemical_formula_sum 'C22 H31 F6 I2 N4 Ni O P' _chemical_formula_weight 824.99 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' I I -0.4742 1.8119 '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/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 17.8197(14) _cell_length_b 8.1460(6) _cell_length_c 19.6976(15) _cell_angle_alpha 90.00 _cell_angle_beta 97.5100(10) _cell_angle_gamma 90.00 _cell_volume 2834.8(4) _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 lath _exptl_crystal_colour orange _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.933 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 2.982 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6978 _exptl_absorpt_correction_T_max 0.8900 _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 30718 _diffrn_reflns_av_R_equivalents 0.1387 _diffrn_reflns_av_sigmaI/netI 0.0840 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.24 _reflns_number_total 6475 _reflns_number_gt 5379 _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^)+(0.0522P)^2^+17.2186P] 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 6475 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1054 _refine_ls_R_factor_gt 0.0864 _refine_ls_wR_factor_ref 0.1714 _refine_ls_wR_factor_gt 0.1636 _refine_ls_goodness_of_fit_ref 1.219 _refine_ls_restrained_S_all 1.219 _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 C11 C -0.0971(7) 0.2310(13) 0.1432(6) 0.039(3) Uani 1 1 d . . . H11A H -0.1493 0.2657 0.1461 0.058 Uiso 1 1 calc R . . H11B H -0.0721 0.3127 0.1173 0.058 Uiso 1 1 calc R . . H11C H -0.0697 0.2213 0.1895 0.058 Uiso 1 1 calc R . . C2 C -0.0165(7) 0.0023(15) 0.1013(5) 0.044(3) Uani 1 1 d . . . H2A H -0.0206 -0.0922 0.0694 0.053 Uiso 1 1 calc R . . H2B H 0.0095 0.0911 0.0793 0.053 Uiso 1 1 calc R . . C10 C 0.1170(7) -0.0575(17) 0.1514(7) 0.052(3) Uani 1 1 d . . . H10A H 0.1481 -0.0918 0.1937 0.078 Uiso 1 1 calc R . . H10B H 0.1338 0.0506 0.1376 0.078 Uiso 1 1 calc R . . H10C H 0.1224 -0.1374 0.1151 0.078 Uiso 1 1 calc R . . C12 C -0.1392(8) 0.0829(14) 0.0333(5) 0.049(3) Uani 1 1 d . . . H12A H -0.1911 0.1207 0.0356 0.073 Uiso 1 1 calc R . . H12B H -0.1406 -0.0226 0.0093 0.073 Uiso 1 1 calc R . . H12C H -0.1125 0.1639 0.0086 0.073 Uiso 1 1 calc R . . I2 I 0.05459(3) 0.20926(8) 0.46761(3) 0.02642(17) Uani 1 1 d . . . I1 I -0.24867(3) 0.51539(7) 0.48928(3) 0.02997(18) Uani 1 1 d . . . Ni1 Ni -0.09315(7) -0.03349(14) 0.24694(6) 0.0229(3) Uani 1 1 d . . . O1 O -0.0416(3) 0.0683(8) 0.3327(3) 0.0270(14) Uani 1 1 d . . . N3 N -0.1062(5) -0.2721(10) 0.2829(5) 0.035(2) Uani 1 1 d . . . N1 N 0.0118(4) -0.0836(11) 0.2201(4) 0.0322(19) Uani 1 1 d . . . C20 C -0.0592(5) 0.2364(11) 0.4286(5) 0.0246(19) Uani 1 1 d . . . N4 N -0.1853(4) 0.0967(9) 0.2806(4) 0.0235(16) Uani 1 1 d . . . C18 C -0.1819(5) 0.3568(11) 0.4369(5) 0.025(2) Uani 1 1 d . . . C17 C -0.2119(5) 0.2793(10) 0.3750(5) 0.0214(18) Uani 1 1 d . . . C5 C -0.1812(6) -0.3461(12) 0.1668(6) 0.041(3) Uani 1 1 d . . . H5A H -0.2003 -0.4450 0.1408 0.049 Uiso 1 1 calc R . . H5B H -0.2248 -0.2923 0.1840 0.049 Uiso 1 1 calc R . . C16 C -0.2885(5) 0.2906(12) 0.3428(6) 0.033(2) Uani 1 1 d . . . H16 H -0.3239 0.3570 0.3623 0.039 Uiso 1 1 calc R . . C1 C 0.0340(6) -0.0480(12) 0.1632(6) 0.036(2) Uani 1 1 d . . . N2 N -0.1401(5) -0.0548(9) 0.1469(4) 0.0271(17) Uani 1 1 d . . . H2 H -0.1891 -0.0138 0.1446 0.033 Uiso 1 1 calc R . . C19 C -0.1076(5) 0.3348(10) 0.4639(5) 0.0243(19) Uani 1 1 d . . . H19 H -0.0885 0.3851 0.5062 0.029 Uiso 1 1 calc R . . C9 C 0.0632(6) -0.1513(14) 0.2768(6) 0.038(3) Uani 1 1 d . . . H9A H 0.0658 -0.0764 0.3166 0.045 Uiso 1 1 calc R . . H9B H 0.1147 -0.1603 0.2633 0.045 Uiso 1 1 calc R . . C4 C -0.1474(6) -0.2274(12) 0.1181(6) 0.036(2) Uani 1 1 d . . . H4A H -0.0968 -0.2675 0.1101 0.043 Uiso 1 1 calc R . . H4B H -0.1802 -0.2255 0.0734 0.043 Uiso 1 1 calc R . . C22 C -0.1636(5) 0.1797(11) 0.3405(5) 0.0231(19) Uani 1 1 d . . . C21 C -0.0846(5) 0.1568(11) 0.3664(5) 0.0213(18) Uani 1 1 d . . . C3 C -0.0976(7) 0.0620(13) 0.1065(6) 0.038(2) Uani 1 1 d . . . C13 C -0.1683(7) -0.2698(13) 0.3263(6) 0.041(3) Uani 1 1 d . . . H13A H -0.1575 -0.1867 0.3622 0.061 Uiso 1 1 calc R . . H13B H -0.1723 -0.3779 0.3474 0.061 Uiso 1 1 calc R . . H13C H -0.2161 -0.2432 0.2980 0.061 Uiso 1 1 calc R . . C8 C 0.0363(6) -0.3219(15) 0.2971(6) 0.045(3) Uani 1 1 d . . . H8A H 0.0300 -0.3921 0.2557 0.055 Uiso 1 1 calc R . . H8B H 0.0767 -0.3714 0.3301 0.055 Uiso 1 1 calc R . . C15 C -0.3104(6) 0.2047(13) 0.2833(6) 0.035(2) Uani 1 1 d . . . H15 H -0.3614 0.2098 0.2621 0.042 Uiso 1 1 calc R . . C14 C -0.2580(5) 0.1111(12) 0.2544(5) 0.030(2) Uani 1 1 d . . . H14 H -0.2749 0.0533 0.2133 0.036 Uiso 1 1 calc R . . C6 C -0.1237(6) -0.3992(12) 0.2283(5) 0.033(2) Uani 1 1 d . . . H6A H -0.1436 -0.4981 0.2491 0.039 Uiso 1 1 calc R . . H6B H -0.0760 -0.4307 0.2111 0.039 Uiso 1 1 calc R . . C7 C -0.0363(6) -0.3254(14) 0.3284(6) 0.038(2) Uani 1 1 d . . . H7A H -0.0444 -0.4388 0.3440 0.045 Uiso 1 1 calc R . . H7B H -0.0301 -0.2541 0.3694 0.045 Uiso 1 1 calc R . . P1 P 0.1238(2) 0.4461(4) 0.0726(2) 0.0557(10) Uani 1 1 d . . . F2 F 0.1839(4) 0.5723(8) 0.1101(4) 0.0513(18) Uani 1 1 d . . . F6 F 0.1876(5) 0.3024(9) 0.0849(4) 0.068(2) Uani 1 1 d . . . F5 F 0.0951(4) 0.3970(11) 0.1424(4) 0.067(2) Uani 1 1 d . . . F1 F 0.0676(6) 0.3172(10) 0.0338(4) 0.081(3) Uani 1 1 d . . . F3 F 0.1543(6) 0.4911(11) 0.0006(4) 0.089(3) Uani 1 1 d . . . F4 F 0.0622(5) 0.5904(11) 0.0624(6) 0.097(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.052(7) 0.033(5) 0.035(6) 0.004(5) 0.022(5) -0.009(5) C2 0.058(7) 0.046(6) 0.032(6) -0.007(5) 0.025(5) -0.013(6) C10 0.050(7) 0.059(8) 0.057(8) -0.013(6) 0.047(6) -0.006(6) C12 0.094(10) 0.032(6) 0.022(6) 0.008(5) 0.015(6) -0.013(6) I2 0.0187(3) 0.0349(3) 0.0273(3) -0.0066(3) 0.0093(2) -0.0020(2) I1 0.0264(3) 0.0227(3) 0.0459(4) -0.0107(3) 0.0238(3) -0.0023(2) Ni1 0.0239(6) 0.0248(6) 0.0222(6) 0.0001(5) 0.0108(5) -0.0008(4) O1 0.021(3) 0.035(3) 0.028(4) -0.006(3) 0.015(3) 0.004(3) N3 0.045(5) 0.032(4) 0.032(5) 0.012(4) 0.023(4) 0.007(4) N1 0.026(4) 0.039(5) 0.035(5) -0.015(4) 0.015(4) -0.005(4) C20 0.019(4) 0.024(4) 0.034(5) 0.001(4) 0.013(4) -0.006(3) N4 0.027(4) 0.026(4) 0.020(4) 0.004(3) 0.010(3) 0.000(3) C18 0.030(5) 0.021(4) 0.028(5) 0.001(4) 0.022(4) -0.001(4) C17 0.024(4) 0.016(4) 0.027(5) 0.001(4) 0.015(4) 0.000(3) C5 0.048(7) 0.020(5) 0.057(8) 0.008(5) 0.014(6) -0.008(4) C16 0.018(4) 0.030(5) 0.052(7) 0.006(5) 0.016(4) 0.003(4) C1 0.042(6) 0.032(5) 0.038(6) -0.018(5) 0.020(5) -0.006(4) N2 0.037(5) 0.021(4) 0.024(4) 0.004(3) 0.009(3) 0.000(3) C19 0.023(4) 0.019(4) 0.034(5) -0.001(4) 0.016(4) -0.001(3) C9 0.025(5) 0.052(7) 0.039(6) -0.012(5) 0.015(5) 0.002(5) C4 0.047(6) 0.025(5) 0.033(6) 0.001(4) 0.001(5) -0.005(4) C22 0.029(5) 0.022(4) 0.020(5) 0.006(4) 0.011(4) -0.005(4) C21 0.022(4) 0.023(4) 0.022(5) 0.005(4) 0.016(4) -0.004(3) C3 0.053(7) 0.029(5) 0.033(6) -0.003(5) 0.014(5) -0.007(5) C13 0.054(7) 0.033(5) 0.044(7) 0.012(5) 0.036(6) 0.003(5) C8 0.042(6) 0.053(7) 0.040(7) -0.005(6) 0.000(5) 0.022(6) C15 0.025(5) 0.041(6) 0.038(6) 0.010(5) 0.002(4) 0.005(4) C14 0.028(5) 0.031(5) 0.032(6) 0.004(4) 0.009(4) -0.005(4) C6 0.035(5) 0.024(5) 0.041(6) 0.002(4) 0.015(5) 0.005(4) C7 0.046(6) 0.037(6) 0.034(6) 0.010(5) 0.015(5) 0.010(5) P1 0.060(2) 0.0384(16) 0.061(2) 0.0145(16) -0.0201(18) -0.0160(15) F2 0.043(4) 0.040(3) 0.067(5) 0.001(4) -0.007(3) 0.002(3) F6 0.089(6) 0.044(4) 0.072(6) 0.004(4) 0.016(5) -0.008(4) F5 0.044(4) 0.083(6) 0.073(6) -0.011(5) 0.002(4) -0.003(4) F1 0.124(8) 0.057(5) 0.057(5) 0.014(4) -0.014(5) -0.037(5) F3 0.129(8) 0.077(6) 0.055(5) 0.025(5) -0.011(5) -0.045(6) F4 0.059(5) 0.052(5) 0.165(10) 0.015(6) -0.043(6) -0.003(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 C11 C3 1.556(14) . ? C2 C1 1.476(16) . ? C2 C3 1.541(16) . ? C10 C1 1.530(14) . ? C12 C3 1.541(15) . ? I2 C20 2.085(9) . ? I1 C18 2.114(9) . ? Ni1 O1 1.996(7) . ? Ni1 N2 2.045(8) . ? Ni1 N1 2.051(8) . ? Ni1 N3 2.092(8) . ? Ni1 N4 2.133(7) . ? O1 C21 1.295(10) . ? N3 C13 1.484(12) . ? N3 C6 1.498(13) . ? N3 C7 1.499(14) . ? N1 C1 1.268(13) . ? N1 C9 1.458(14) . ? C20 C21 1.407(13) . ? C20 C19 1.424(12) . ? N4 C14 1.336(12) . ? N4 C22 1.370(12) . ? C18 C19 1.373(13) . ? C18 C17 1.414(13) . ? C17 C22 1.419(12) . ? C17 C16 1.430(13) . ? C5 C4 1.539(14) . ? C5 C6 1.543(15) . ? C16 C15 1.377(15) . ? N2 C3 1.506(13) . ? N2 C4 1.516(12) . ? C9 C8 1.540(17) . ? C22 C21 1.446(13) . ? C8 C7 1.505(15) . ? C15 C14 1.384(14) . ? P1 F1 1.579(8) . ? P1 F5 1.580(9) . ? P1 F2 1.594(7) . ? P1 F4 1.603(9) . ? P1 F3 1.626(10) . ? P1 F6 1.627(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 C3 120.7(9) . . ? O1 Ni1 N2 159.4(3) . . ? O1 Ni1 N1 88.1(3) . . ? N2 Ni1 N1 90.4(3) . . ? O1 Ni1 N3 99.1(3) . . ? N2 Ni1 N3 101.4(3) . . ? N1 Ni1 N3 92.8(3) . . ? O1 Ni1 N4 79.5(3) . . ? N2 Ni1 N4 96.2(3) . . ? N1 Ni1 N4 160.9(3) . . ? N3 Ni1 N4 103.4(3) . . ? C21 O1 Ni1 115.2(6) . . ? C13 N3 C6 108.7(9) . . ? C13 N3 C7 106.5(8) . . ? C6 N3 C7 107.9(8) . . ? C13 N3 Ni1 107.9(6) . . ? C6 N3 Ni1 114.9(6) . . ? C7 N3 Ni1 110.6(7) . . ? C1 N1 C9 121.7(9) . . ? C1 N1 Ni1 125.6(8) . . ? C9 N1 Ni1 112.4(6) . . ? C21 C20 C19 122.6(8) . . ? C21 C20 I2 117.3(6) . . ? C19 C20 I2 120.1(7) . . ? C14 N4 C22 116.1(8) . . ? C14 N4 Ni1 132.1(7) . . ? C22 N4 Ni1 111.8(6) . . ? C19 C18 C17 120.9(8) . . ? C19 C18 I1 117.8(7) . . ? C17 C18 I1 121.3(7) . . ? C18 C17 C22 118.9(8) . . ? C18 C17 C16 125.8(8) . . ? C22 C17 C16 115.3(8) . . ? C4 C5 C6 113.1(9) . . ? C15 C16 C17 119.5(9) . . ? N1 C1 C2 124.5(10) . . ? N1 C1 C10 122.8(11) . . ? C2 C1 C10 112.7(9) . . ? C3 N2 C4 114.4(8) . . ? C3 N2 Ni1 106.6(6) . . ? C4 N2 Ni1 116.4(6) . . ? C18 C19 C20 119.9(9) . . ? N1 C9 C8 110.8(9) . . ? N2 C4 C5 111.8(9) . . ? N4 C22 C17 125.0(8) . . ? N4 C22 C21 113.1(8) . . ? C17 C22 C21 121.9(8) . . ? O1 C21 C20 123.9(8) . . ? O1 C21 C22 120.4(8) . . ? C20 C21 C22 115.7(8) . . ? N2 C3 C2 112.0(9) . . ? N2 C3 C12 110.5(9) . . ? C2 C3 C12 108.3(9) . . ? N2 C3 C11 106.6(8) . . ? C2 C3 C11 111.2(9) . . ? C12 C3 C11 108.1(9) . . ? C7 C8 C9 115.9(9) . . ? C16 C15 C14 119.9(9) . . ? N4 C14 C15 124.1(10) . . ? N3 C6 C5 115.2(8) . . ? N3 C7 C8 116.2(9) . . ? F1 P1 F5 89.8(5) . . ? F1 P1 F2 177.2(6) . . ? F5 P1 F2 92.0(4) . . ? F1 P1 F4 92.6(5) . . ? F5 P1 F4 90.1(6) . . ? F2 P1 F4 89.6(4) . . ? F1 P1 F3 89.5(5) . . ? F5 P1 F3 178.3(6) . . ? F2 P1 F3 88.7(5) . . ? F4 P1 F3 91.5(6) . . ? F1 P1 F6 88.8(5) . . ? F5 P1 F6 89.3(5) . . ? F2 P1 F6 88.9(4) . . ? F4 P1 F6 178.4(5) . . ? F3 P1 F6 89.1(5) . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 0.50 _diffrn_measured_fraction_theta_full 0.000 _refine_diff_density_max 2.034 _refine_diff_density_min -1.831 _refine_diff_density_rms 0.198