# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Thomas Braun' 'Beate Neumann' 'Marianna I. Sladek' 'Hans-Georg Stammler' _publ_contact_author_name 'Dr Thomas Braun' _publ_contact_author_address ; Fakultat fur Chemie, AC III Universitat Bielefeld Postfach 100131 33501 Bielefeld D-33501 GERMANY ; _publ_contact_author_email THOMAS.BRAUN@UNI-BIELEFELD.DE _publ_requested_journal 'New Journal of Chemistry' _publ_requested_coeditor_name ? _publ_section_title ; Synthesis, Structure and Reactivity of 3-Fluoropyridyl Nickel Complexes: Formation of New 2,4,5,6-Tetra fluoropyridines ; data_compound1 _database_code_CSD 190943 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H30 Cl F4 N Ni P2' _chemical_formula_sum 'C17 H30 Cl F4 N Ni P2' _chemical_formula_weight 480.52 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' 'Cl' 'Cl' 0.1484 0.1585 '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' '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 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 23.36300(10) _cell_length_b 8.55400(10) _cell_length_c 10.9840(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2195.12(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3628 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 1.19 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7174 _exptl_absorpt_correction_T_max 0.8422 _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 'KappaCCD' _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43259 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6102 _reflns_number_gt 5943 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD ' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 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^)+(0.0226P)^2^+0.7712P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0029(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.499(6) _refine_ls_number_reflns 6102 _refine_ls_number_parameters 243 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0216 _refine_ls_R_factor_gt 0.0205 _refine_ls_wR_factor_ref 0.0513 _refine_ls_wR_factor_gt 0.0508 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.151038(7) 0.367091(18) 0.974608(18) 0.01283(4) Uani 1 1 d . . . Cl1 Cl 0.176420(15) 0.45390(5) 1.15446(3) 0.02299(8) Uani 1 1 d . . . P1 P 0.060071(15) 0.38862(4) 1.02905(3) 0.01551(7) Uani 1 1 d . . . P2 P 0.240776(15) 0.39404(4) 0.91120(3) 0.01390(7) Uani 1 1 d . . . F1 F 0.13987(4) 0.01559(11) 0.91514(9) 0.02412(19) Uani 1 1 d . . . F2 F 0.10818(5) -0.12745(10) 0.70568(10) 0.0281(2) Uani 1 1 d . . . F3 F 0.08407(4) 0.05203(13) 0.50652(9) 0.0303(2) Uani 1 1 d . . . F4 F 0.11451(4) 0.49621(10) 0.71565(9) 0.02240(18) Uani 1 1 d . . . N1 N 0.10046(5) 0.27355(16) 0.61379(12) 0.0207(2) Uani 1 1 d . . . C1 C 0.13030(6) 0.26654(16) 0.82741(13) 0.0146(2) Uani 1 1 d . . . C2 C 0.12760(6) 0.10507(16) 0.81805(14) 0.0167(3) Uani 1 1 d . . . C3 C 0.11182(6) 0.02815(16) 0.71169(15) 0.0195(3) Uani 1 1 d . . . C4 C 0.09929(6) 0.12037(19) 0.61271(14) 0.0219(3) Uani 1 1 d . . . C5 C 0.11527(6) 0.33832(16) 0.71852(13) 0.0162(2) Uani 1 1 d . . . C6 C 0.00582(6) 0.33712(19) 0.91502(14) 0.0217(3) Uani 1 1 d . . . H6A H 0.0142 0.3963 0.8397 0.026 Uiso 1 1 calc R . . H6B H 0.0101 0.2247 0.8956 0.026 Uiso 1 1 calc R . . C7 C -0.05668(6) 0.3669(2) 0.94948(15) 0.0258(3) Uani 1 1 d . . . H7A H -0.0664 0.3057 1.0220 0.039 Uiso 1 1 calc R . . H7B H -0.0816 0.3358 0.8819 0.039 Uiso 1 1 calc R . . H7C H -0.0621 0.4784 0.9666 0.039 Uiso 1 1 calc R . . C8 C 0.03940(7) 0.28285(19) 1.16693(15) 0.0244(3) Uani 1 1 d . . . H8A H 0.0648 0.3157 1.2344 0.029 Uiso 1 1 calc R . . H8B H -0.0002 0.3128 1.1890 0.029 Uiso 1 1 calc R . . C9 C 0.04236(8) 0.1056(2) 1.1546(2) 0.0335(4) Uani 1 1 d . . . H9A H 0.0147 0.0709 1.0932 0.050 Uiso 1 1 calc R . . H9B H 0.0332 0.0571 1.2331 0.050 Uiso 1 1 calc R . . H9C H 0.0810 0.0749 1.1297 0.050 Uiso 1 1 calc R . . C10 C 0.04350(7) 0.59112(19) 1.07025(14) 0.0217(3) Uani 1 1 d . . . H10A H 0.0040 0.5955 1.1029 0.026 Uiso 1 1 calc R . . H10B H 0.0698 0.6245 1.1360 0.026 Uiso 1 1 calc R . . C11 C 0.04845(8) 0.70571(18) 0.9648(2) 0.0325(4) Uani 1 1 d . . . H11A H 0.0865 0.6968 0.9280 0.049 Uiso 1 1 calc R . . H11B H 0.0428 0.8125 0.9949 0.049 Uiso 1 1 calc R . . H11C H 0.0192 0.6817 0.9037 0.049 Uiso 1 1 calc R . . C12 C 0.25716(6) 0.34498(17) 0.75239(13) 0.0175(3) Uani 1 1 d . . . H12A H 0.2515 0.2312 0.7413 0.021 Uiso 1 1 calc R . . H12B H 0.2292 0.3991 0.6994 0.021 Uiso 1 1 calc R . . C13 C 0.31750(7) 0.3870(2) 0.70886(17) 0.0261(3) Uani 1 1 d . . . H13A H 0.3227 0.5006 0.7126 0.039 Uiso 1 1 calc R . . H13B H 0.3226 0.3513 0.6248 0.039 Uiso 1 1 calc R . . H13C H 0.3458 0.3359 0.7613 0.039 Uiso 1 1 calc R . . C14 C 0.29355(6) 0.28506(17) 0.99934(13) 0.0186(3) Uani 1 1 d . . . H14A H 0.3324 0.3176 0.9738 0.022 Uiso 1 1 calc R . . H14B H 0.2891 0.3116 1.0866 0.022 Uiso 1 1 calc R . . C15 C 0.28787(7) 0.10790(17) 0.98374(18) 0.0246(3) Uani 1 1 d . . . H15A H 0.2488 0.0757 1.0041 0.037 Uiso 1 1 calc R . . H15B H 0.3149 0.0550 1.0380 0.037 Uiso 1 1 calc R . . H15C H 0.2963 0.0796 0.8992 0.037 Uiso 1 1 calc R . . C16 C 0.26364(7) 0.59740(17) 0.92850(16) 0.0226(3) Uani 1 1 d . . . H16A H 0.2624 0.6262 1.0158 0.027 Uiso 1 1 calc R . . H16B H 0.3037 0.6077 0.9004 0.027 Uiso 1 1 calc R . . C17 C 0.22592(8) 0.70994(19) 0.8565(2) 0.0333(4) Uani 1 1 d . . . H17A H 0.2270 0.6820 0.7700 0.050 Uiso 1 1 calc R . . H17B H 0.2401 0.8170 0.8670 0.050 Uiso 1 1 calc R . . H17C H 0.1864 0.7031 0.8862 0.050 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 Ni1 0.01042(7) 0.01627(7) 0.01182(7) -0.00139(7) 0.00004(6) -0.00014(6) Cl1 0.01752(15) 0.03510(19) 0.01635(15) -0.00827(14) -0.00181(13) -0.00066(13) P1 0.01166(15) 0.02141(17) 0.01347(15) -0.00223(13) 0.00161(13) -0.00081(12) P2 0.01085(15) 0.01666(15) 0.01419(16) -0.00028(13) -0.00039(12) -0.00003(11) F1 0.0316(5) 0.0197(4) 0.0211(5) 0.0030(4) -0.0028(4) 0.0010(3) F2 0.0333(5) 0.0200(4) 0.0309(5) -0.0065(4) -0.0001(4) -0.0012(4) F3 0.0284(5) 0.0426(6) 0.0200(5) -0.0129(4) -0.0042(4) -0.0006(4) F4 0.0276(5) 0.0175(4) 0.0221(4) 0.0033(3) -0.0010(4) 0.0015(3) N1 0.0167(6) 0.0305(6) 0.0150(5) -0.0003(5) -0.0002(4) 0.0007(5) C1 0.0104(5) 0.0183(6) 0.0150(6) -0.0018(5) -0.0003(5) 0.0008(4) C2 0.0138(6) 0.0195(6) 0.0167(6) -0.0001(5) 0.0010(5) 0.0014(5) C3 0.0156(6) 0.0199(6) 0.0232(7) -0.0075(6) 0.0015(5) -0.0002(5) C4 0.0142(6) 0.0343(8) 0.0172(7) -0.0085(6) 0.0000(5) -0.0005(5) C5 0.0134(6) 0.0185(6) 0.0165(6) -0.0005(5) 0.0014(5) 0.0007(5) C6 0.0132(6) 0.0324(7) 0.0194(7) -0.0070(6) -0.0001(5) -0.0030(5) C7 0.0122(6) 0.0397(8) 0.0255(9) -0.0035(6) 0.0019(5) -0.0024(6) C8 0.0198(7) 0.0342(8) 0.0193(7) 0.0037(6) 0.0040(6) -0.0020(6) C9 0.0260(8) 0.0333(9) 0.0412(10) 0.0104(8) 0.0053(8) 0.0009(6) C10 0.0176(7) 0.0262(7) 0.0212(7) -0.0062(5) 0.0011(5) 0.0040(5) C11 0.0380(9) 0.0227(7) 0.0368(9) 0.0006(7) 0.0056(8) 0.0004(6) C12 0.0154(6) 0.0241(7) 0.0132(6) 0.0016(5) 0.0021(5) 0.0010(5) C13 0.0171(7) 0.0382(9) 0.0229(7) 0.0016(7) 0.0057(6) -0.0003(6) C14 0.0127(5) 0.0264(7) 0.0168(7) 0.0022(5) -0.0022(5) 0.0022(5) C15 0.0224(7) 0.0251(7) 0.0265(7) 0.0087(7) -0.0013(7) 0.0041(5) C16 0.0193(7) 0.0197(6) 0.0287(8) -0.0041(6) 0.0020(6) -0.0057(5) C17 0.0356(9) 0.0172(7) 0.0470(11) 0.0048(7) 0.0005(8) -0.0011(6) _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 C1 1.8943(14) . ? Ni1 Cl1 2.1921(4) . ? Ni1 P1 2.2155(4) . ? Ni1 P2 2.2212(4) . ? P1 C8 1.8290(16) . ? P1 C10 1.8318(16) . ? P1 C6 1.8355(15) . ? P2 C14 1.8238(14) . ? P2 C16 1.8296(15) . ? P2 C12 1.8345(15) . ? F1 C2 1.3436(17) . ? F2 C3 1.3353(16) . ? F3 C4 1.3524(17) . ? F4 C5 1.3511(15) . ? N1 C4 1.311(2) . ? N1 C5 1.3228(19) . ? C1 C2 1.3865(19) . ? C1 C5 1.3896(19) . ? C2 C3 1.391(2) . ? C3 C4 1.375(2) . ? C6 C7 1.530(2) . ? C8 C9 1.523(2) . ? C10 C11 1.521(3) . ? C12 C13 1.531(2) . ? C14 C15 1.531(2) . ? C16 C17 1.526(2) . ? 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 Ni1 Cl1 172.80(4) . . ? C1 Ni1 P1 91.31(4) . . ? Cl1 Ni1 P1 89.318(15) . . ? C1 Ni1 P2 91.20(4) . . ? Cl1 Ni1 P2 89.545(14) . . ? P1 Ni1 P2 168.951(14) . . ? C8 P1 C10 101.97(8) . . ? C8 P1 C6 105.31(8) . . ? C10 P1 C6 104.45(7) . . ? C8 P1 Ni1 115.83(5) . . ? C10 P1 Ni1 110.37(5) . . ? C6 P1 Ni1 117.27(5) . . ? C14 P2 C16 103.50(7) . . ? C14 P2 C12 104.28(7) . . ? C16 P2 C12 104.79(7) . . ? C14 P2 Ni1 114.75(5) . . ? C16 P2 Ni1 109.98(5) . . ? C12 P2 Ni1 118.12(5) . . ? C4 N1 C5 115.59(13) . . ? C2 C1 C5 111.39(13) . . ? C2 C1 Ni1 121.82(11) . . ? C5 C1 Ni1 126.77(10) . . ? F1 C2 C1 119.92(13) . . ? F1 C2 C3 116.99(12) . . ? C1 C2 C3 123.08(13) . . ? F2 C3 C4 121.29(14) . . ? F2 C3 C2 122.01(14) . . ? C4 C3 C2 116.70(13) . . ? N1 C4 F3 116.45(14) . . ? N1 C4 C3 124.20(14) . . ? F3 C4 C3 119.35(14) . . ? N1 C5 F4 113.26(12) . . ? N1 C5 C1 129.02(13) . . ? F4 C5 C1 117.72(12) . . ? C7 C6 P1 116.76(11) . . ? C9 C8 P1 114.00(12) . . ? C11 C10 P1 113.90(11) . . ? C13 C12 P2 115.81(11) . . ? C15 C14 P2 112.83(10) . . ? C17 C16 P2 112.17(11) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.615 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.046 #============================================================================== data_compound3 _database_code_CSD 190944 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H33 F4 N Ni P2' _chemical_formula_sum 'C18 H33 F4 N Ni P2' _chemical_formula_weight 460.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' '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 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 23.4610(3) _cell_length_b 8.7220(4) _cell_length_c 10.8680(9) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 2223.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.051 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.726 _exptl_absorpt_correction_T_max 0.830 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 173(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 'KappaCCD' _diffrn_measurement_method 'CCD; rotation images; fine slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18038 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6029 _reflns_number_gt 5201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD ' _computing_cell_refinement ? _computing_data_reduction 'EVALCCD (Duisenberg, 1998, Thesis. Utrecht Un' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 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^)+(0.0353P)^2^+1.1748P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0006(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.019(11) _refine_ls_number_reflns 6029 _refine_ls_number_parameters 243 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0762 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.001 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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.150348(11) 0.14141(3) 0.18080(3) 0.02414(8) Uani 1 1 d . . . P1 P 0.06120(3) 0.11925(8) 0.12370(6) 0.02900(14) Uani 1 1 d . . . P2 P 0.23889(2) 0.11061(8) 0.23816(5) 0.02541(13) Uani 1 1 d . . . F1 F 0.13858(7) 0.4893(2) 0.24627(17) 0.0441(4) Uani 1 1 d . . . F2 F 0.10684(9) 0.6271(2) 0.4555(2) 0.0583(5) Uani 1 1 d . . . F3 F 0.08306(8) 0.4532(3) 0.65608(16) 0.0636(6) Uani 1 1 d . . . F4 F 0.11527(8) 0.0178(2) 0.44655(15) 0.0420(4) Uani 1 1 d . . . N1 N 0.10008(9) 0.2358(3) 0.5489(2) 0.0389(6) Uani 1 1 d . . . C1 C 0.00746(11) 0.1688(4) 0.2392(3) 0.0386(6) Uani 1 1 d . . . H1A H 0.0164 0.1115 0.3154 0.046 Uiso 1 1 calc R . . H1B H 0.0115 0.2793 0.2584 0.046 Uiso 1 1 calc R . . C2 C -0.05506(11) 0.1384(4) 0.2069(3) 0.0462(8) Uani 1 1 d . . . H2A H -0.0661 0.2026 0.1368 0.069 Uiso 1 1 calc R . . H2B H -0.0791 0.1632 0.2778 0.069 Uiso 1 1 calc R . . H2C H -0.0599 0.0301 0.1853 0.069 Uiso 1 1 calc R . . C3 C 0.04242(13) -0.0780(4) 0.0809(3) 0.0453(7) Uani 1 1 d . . . H3A H 0.0020 -0.0805 0.0551 0.054 Uiso 1 1 calc R . . H3B H 0.0658 -0.1091 0.0094 0.054 Uiso 1 1 calc R . . C4 C 0.05105(16) -0.1931(4) 0.1834(5) 0.0653(9) Uani 1 1 d . . . H4A H 0.0904 -0.1872 0.2131 0.098 Uiso 1 1 calc R . . H4B H 0.0435 -0.2966 0.1524 0.098 Uiso 1 1 calc R . . H4C H 0.0248 -0.1702 0.2512 0.098 Uiso 1 1 calc R . . C5 C 0.03864(13) 0.2255(4) -0.0127(3) 0.0470(8) Uani 1 1 d . . . H5A H 0.0621 0.1923 -0.0836 0.056 Uiso 1 1 calc R . . H5B H -0.0015 0.1991 -0.0311 0.056 Uiso 1 1 calc R . . C6 C 0.04358(16) 0.3984(5) 0.0008(5) 0.0692(12) Uani 1 1 d . . . H6A H 0.0205 0.4325 0.0707 0.104 Uiso 1 1 calc R . . H6B H 0.0299 0.4481 -0.0746 0.104 Uiso 1 1 calc R . . H6C H 0.0835 0.4262 0.0148 0.104 Uiso 1 1 calc R . . C7 C 0.26373(12) -0.0857(4) 0.2175(3) 0.0415(7) Uani 1 1 d . . . H7A H 0.2631 -0.1112 0.1287 0.050 Uiso 1 1 calc R . . H7B H 0.3037 -0.0933 0.2462 0.050 Uiso 1 1 calc R . . C8 C 0.22761(18) -0.2018(4) 0.2870(4) 0.0625(10) Uani 1 1 d . . . H8A H 0.2276 -0.1764 0.3749 0.094 Uiso 1 1 calc R . . H8B H 0.2435 -0.3047 0.2754 0.094 Uiso 1 1 calc R . . H8C H 0.1885 -0.1992 0.2556 0.094 Uiso 1 1 calc R . . C9 C 0.29215(11) 0.2234(4) 0.1563(2) 0.0354(6) Uani 1 1 d . . . H9A H 0.3306 0.1909 0.1833 0.042 Uiso 1 1 calc R . . H9B H 0.2890 0.2021 0.0670 0.042 Uiso 1 1 calc R . . C10 C 0.28576(13) 0.3950(3) 0.1776(4) 0.0469(7) Uani 1 1 d . . . H10A H 0.2482 0.4286 0.1487 0.070 Uiso 1 1 calc R . . H10B H 0.3156 0.4499 0.1323 0.070 Uiso 1 1 calc R . . H10C H 0.2894 0.4170 0.2657 0.070 Uiso 1 1 calc R . . C11 C 0.25569(10) 0.1503(3) 0.3996(2) 0.0323(5) Uani 1 1 d . . . H11A H 0.2486 0.2605 0.4151 0.039 Uiso 1 1 calc R . . H11B H 0.2287 0.0916 0.4514 0.039 Uiso 1 1 calc R . . C12 C 0.31621(13) 0.1132(4) 0.4425(3) 0.0475(8) Uani 1 1 d . . . H12A H 0.3236 0.0035 0.4315 0.071 Uiso 1 1 calc R . . H12B H 0.3202 0.1400 0.5296 0.071 Uiso 1 1 calc R . . H12C H 0.3436 0.1725 0.3938 0.071 Uiso 1 1 calc R . . C13 C 0.12955(10) 0.2426(3) 0.3328(2) 0.0277(5) Uani 1 1 d . . . C14 C 0.12649(10) 0.3995(3) 0.3436(2) 0.0312(5) Uani 1 1 d . . . C15 C 0.11071(11) 0.4755(3) 0.4497(3) 0.0361(6) Uani 1 1 d . . . C16 C 0.09834(11) 0.3859(4) 0.5491(2) 0.0422(7) Uani 1 1 d . . . C17 C 0.11509(10) 0.1726(3) 0.4426(2) 0.0308(5) Uani 1 1 d . . . C18 C 0.17271(11) 0.0628(4) 0.0157(2) 0.0399(7) Uani 1 1 d . . . H18A H 0.1540 0.1240 -0.0482 0.060 Uiso 1 1 calc R . . H18B H 0.1610 -0.0446 0.0079 0.060 Uiso 1 1 calc R . . H18C H 0.2142 0.0703 0.0062 0.060 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 Ni1 0.01966(12) 0.03118(15) 0.02158(11) -0.00165(16) 0.00035(11) -0.00022(12) P1 0.0216(3) 0.0408(4) 0.0247(3) -0.0012(3) -0.0020(2) 0.0007(2) P2 0.0198(3) 0.0325(3) 0.0239(3) -0.0008(3) 0.0007(2) 0.0001(2) F1 0.0545(10) 0.0367(10) 0.0410(8) 0.0034(7) 0.0052(8) -0.0002(7) F2 0.0589(12) 0.0492(13) 0.0668(12) -0.0212(10) -0.0018(10) 0.0041(9) F3 0.0505(10) 0.0991(17) 0.0414(10) -0.0321(10) 0.0094(8) 0.0048(11) F4 0.0488(10) 0.0395(10) 0.0377(8) 0.0053(7) 0.0046(7) -0.0025(7) N1 0.0293(11) 0.0590(18) 0.0285(10) -0.0032(10) 0.0026(8) -0.0014(11) C1 0.0236(11) 0.0587(19) 0.0335(13) -0.0080(13) 0.0006(10) 0.0037(11) C2 0.0239(12) 0.073(2) 0.0415(16) -0.0006(14) -0.0013(10) 0.0063(13) C3 0.0310(13) 0.056(2) 0.0490(16) -0.0145(15) 0.0001(12) -0.0076(13) C4 0.059(2) 0.049(2) 0.088(3) 0.003(3) -0.005(2) -0.0054(15) C5 0.0330(14) 0.071(2) 0.0366(14) 0.0127(14) -0.0060(11) 0.0021(14) C6 0.0439(18) 0.075(3) 0.089(3) 0.040(2) -0.0080(18) -0.0040(18) C7 0.0357(14) 0.0400(16) 0.0488(16) -0.0077(12) -0.0061(11) 0.0107(12) C8 0.073(2) 0.0331(19) 0.082(3) 0.0081(18) -0.008(2) -0.0021(17) C9 0.0237(11) 0.0503(17) 0.0321(14) 0.0059(11) 0.0023(9) -0.0022(11) C10 0.0425(15) 0.0443(17) 0.0540(16) 0.0161(18) -0.0002(15) -0.0126(11) C11 0.0252(11) 0.0472(17) 0.0245(10) -0.0003(10) -0.0025(9) -0.0030(11) C12 0.0309(13) 0.071(2) 0.0403(14) -0.0001(15) -0.0093(11) 0.0018(14) C13 0.0188(10) 0.0366(14) 0.0275(11) -0.0035(10) -0.0008(8) -0.0010(9) C14 0.0241(11) 0.0361(15) 0.0333(12) -0.0038(11) -0.0026(9) -0.0011(10) C15 0.0274(12) 0.0402(17) 0.0407(13) -0.0139(12) -0.0023(10) 0.0019(11) C16 0.0257(12) 0.069(2) 0.0316(12) -0.0182(13) 0.0007(10) 0.0016(13) C17 0.0231(10) 0.0404(16) 0.0288(11) -0.0024(10) 0.0007(9) -0.0034(10) C18 0.0273(12) 0.062(2) 0.0302(12) -0.0128(13) 0.0003(10) 0.0013(12) _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 C13 1.936(2) . ? Ni1 C18 1.991(3) . ? Ni1 P2 2.1854(6) . ? Ni1 P1 2.1902(7) . ? P1 C5 1.826(3) . ? P1 C1 1.831(3) . ? P1 C3 1.836(3) . ? P2 C9 1.822(3) . ? P2 C7 1.823(3) . ? P2 C11 1.831(2) . ? F1 C14 1.346(3) . ? F2 C15 1.327(3) . ? F3 C16 1.351(3) . ? F4 C17 1.351(3) . ? N1 C16 1.309(4) . ? N1 C17 1.328(3) . ? C1 C2 1.531(4) . ? C3 C4 1.514(6) . ? C5 C6 1.520(6) . ? C7 C8 1.522(5) . ? C9 C10 1.522(4) . ? C11 C12 1.529(4) . ? C13 C14 1.375(4) . ? C13 C17 1.383(4) . ? C14 C15 1.380(4) . ? C15 C16 1.364(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 C13 Ni1 C18 173.02(13) . . ? C13 Ni1 P2 92.99(7) . . ? C18 Ni1 P2 87.95(8) . . ? C13 Ni1 P1 92.37(7) . . ? C18 Ni1 P1 88.05(8) . . ? P2 Ni1 P1 167.87(3) . . ? C5 P1 C1 103.72(14) . . ? C5 P1 C3 101.56(16) . . ? C1 P1 C3 103.28(14) . . ? C5 P1 Ni1 117.51(10) . . ? C1 P1 Ni1 116.26(9) . . ? C3 P1 Ni1 112.56(10) . . ? C9 P2 C7 103.15(14) . . ? C9 P2 C11 102.61(12) . . ? C7 P2 C11 103.12(14) . . ? C9 P2 Ni1 116.50(9) . . ? C7 P2 Ni1 112.59(10) . . ? C11 P2 Ni1 117.04(8) . . ? C16 N1 C17 115.1(3) . . ? C2 C1 P1 117.5(2) . . ? C4 C3 P1 113.8(2) . . ? C6 C5 P1 113.8(3) . . ? C8 C7 P2 112.7(2) . . ? C10 C9 P2 112.86(19) . . ? C12 C11 P2 116.87(19) . . ? C14 C13 C17 110.7(2) . . ? C14 C13 Ni1 122.66(19) . . ? C17 C13 Ni1 126.6(2) . . ? F1 C14 C13 120.0(2) . . ? F1 C14 C15 115.7(3) . . ? C13 C14 C15 124.3(3) . . ? F2 C15 C16 121.2(3) . . ? F2 C15 C14 122.5(3) . . ? C16 C15 C14 116.3(3) . . ? N1 C16 F3 116.3(3) . . ? N1 C16 C15 124.4(2) . . ? F3 C16 C15 119.3(3) . . ? N1 C17 F4 112.8(2) . . ? N1 C17 C13 129.2(3) . . ? F4 C17 C13 117.9(2) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.898 _refine_diff_density_min -0.701 _refine_diff_density_rms 0.125