Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'M. Dolores Santana' _publ_contact_author_address ; Departamento de Quimica Inorganica Universidad de Murcia 30071 Murcia Spain ; _publ_contact_author_email DSL@UM.ES _publ_section_title ; Five-coordinate nickel(II) complexes with carboxylate anions and derivatives of 1,5,9-triazacyclododec-1-ene: structural and 1H NMR spectroscopic studies ; loop_ _publ_author_name 'M. Dolores Santana' 'Gabriel Garcia' 'Gregorio Lopez' 'A. Abel Lozano' 'Jose Perez' data_4 _database_code_depnum_ccdc_archive 'CCDC 249396' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H32 F6 N3 Ni O2 P' _chemical_formula_weight 550.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2367(6) _cell_length_b 15.3163(12) _cell_length_c 18.7672(14) _cell_angle_alpha 90.00 _cell_angle_beta 91.2290(10) _cell_angle_gamma 90.00 _cell_volume 2367.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6460 _cell_measurement_theta_min 2.474 _cell_measurement_theta_max 27.674 _exptl_crystal_description Block _exptl_crystal_colour Blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.957 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8029 _exptl_absorpt_correction_T_max 0.9188 _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 'Bruker APEX' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27013 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 28.15 _reflns_number_total 5464 _reflns_number_gt 5187 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WinGX publication routines (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. ; _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^)+(0.0776P)^2^+8.2283P] 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 5464 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.1766 _refine_ls_wR_factor_gt 0.1743 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.38318(5) 0.83305(3) 0.13548(2) 0.02346(16) Uani 1 1 d . . . N1 N 0.3664(4) 0.9621(2) 0.14424(16) 0.0279(7) Uani 1 1 d . . . N2 N 0.2793(4) 0.8160(2) 0.23064(16) 0.0265(6) Uani 1 1 d . . . H2 H 0.2920 0.7574 0.2424 0.032 Uiso 1 1 calc R . . N3 N 0.1886(4) 0.8223(3) 0.06664(19) 0.0428(10) Uani 1 1 d . . . C1 C 0.3574(4) 1.0078(2) 0.2009(2) 0.0266(7) Uani 1 1 d . . . C2 C 0.3559(5) 0.9660(2) 0.27350(19) 0.0275(7) Uani 1 1 d . . . H2A H 0.2494 0.9794 0.2944 0.033 Uiso 1 1 calc R . . H2B H 0.4393 0.9959 0.3033 0.033 Uiso 1 1 calc R . . C3 C 0.3841(5) 0.8670(2) 0.28213(18) 0.0271(7) Uani 1 1 d . . . C4 C 0.1014(5) 0.8353(3) 0.2333(2) 0.0393(10) Uani 1 1 d . . . H4A H 0.0844 0.8993 0.2313 0.047 Uiso 1 1 calc R . . H4B H 0.0583 0.8138 0.2789 0.047 Uiso 1 1 calc R . . C5 C 0.0086(5) 0.7922(3) 0.1713(3) 0.0467(12) Uani 1 1 d . . . H5A H 0.0462 0.7311 0.1667 0.056 Uiso 1 1 calc R . . H5B H -0.1084 0.7907 0.1824 0.056 Uiso 1 1 calc R . . C6 C 0.0295(5) 0.8382(4) 0.1012(3) 0.0460(12) Uani 1 1 d . . . H6A H -0.0588 0.8194 0.0680 0.055 Uiso 1 1 calc R . . H6B H 0.0170 0.9017 0.1090 0.055 Uiso 1 1 calc R . . C7 C 0.2079(6) 0.8858(4) 0.0066(2) 0.0565(15) Uani 1 1 d . . . H7A H 0.1130 0.8798 -0.0263 0.068 Uiso 1 1 calc R . . H7B H 0.3055 0.8691 -0.0202 0.068 Uiso 1 1 calc R . . C8 C 0.2238(6) 0.9805(4) 0.0273(2) 0.0556(15) Uani 1 1 d . . . H8A H 0.1251 0.9975 0.0532 0.067 Uiso 1 1 calc R . . H8B H 0.2264 1.0158 -0.0168 0.067 Uiso 1 1 calc R . . C9 C 0.3716(6) 1.0045(3) 0.0735(2) 0.0428(11) Uani 1 1 d . . . H9A H 0.4715 0.9863 0.0491 0.051 Uiso 1 1 calc R . . H9B H 0.3757 1.0686 0.0797 0.051 Uiso 1 1 calc R . . C10 C 0.3478(5) 1.1059(3) 0.2028(3) 0.0383(9) Uani 1 1 d . . . H10A H 0.4426 1.1307 0.1795 0.057 Uiso 1 1 calc R . . H10B H 0.3459 1.1257 0.2524 0.057 Uiso 1 1 calc R . . H10C H 0.2486 1.1252 0.1777 0.057 Uiso 1 1 calc R . . C11 C 0.5600(5) 0.8441(3) 0.2658(2) 0.0325(8) Uani 1 1 d . . . H11A H 0.5833 0.8611 0.2167 0.049 Uiso 1 1 calc R . . H11B H 0.5765 0.7811 0.2714 0.049 Uiso 1 1 calc R . . H11C H 0.6331 0.8756 0.2987 0.049 Uiso 1 1 calc R . . C12 C 0.3477(7) 0.8421(3) 0.3595(2) 0.0441(11) Uani 1 1 d . . . H12A H 0.2348 0.8567 0.3698 0.066 Uiso 1 1 calc R . . H12B H 0.4205 0.8744 0.3920 0.066 Uiso 1 1 calc R . . H12C H 0.3646 0.7792 0.3662 0.066 Uiso 1 1 calc R . . C13 C 0.1860(6) 0.7323(4) 0.0357(3) 0.0644(18) Uani 1 1 d . . . H13A H 0.2901 0.7203 0.0134 0.097 Uiso 1 1 calc R . . H13B H 0.0982 0.7280 -0.0002 0.097 Uiso 1 1 calc R . . H13C H 0.1679 0.6896 0.0736 0.097 Uiso 1 1 calc R . . C14 C 0.5723(4) 0.7431(3) 0.07153(18) 0.0268(7) Uani 1 1 d . . . C15 C 0.6690(5) 0.6844(3) 0.02440(19) 0.0303(8) Uani 1 1 d . . . C16 C 0.6762(7) 0.5955(3) 0.0379(3) 0.0505(12) Uani 1 1 d . . . H16 H 0.6247 0.5717 0.0783 0.061 Uiso 1 1 calc R . . C17 C 0.7597(9) 0.5414(4) -0.0084(3) 0.0673(17) Uani 1 1 d . . . H17 H 0.7643 0.4803 0.0004 0.081 Uiso 1 1 calc R . . C18 C 0.8353(6) 0.5756(4) -0.0667(3) 0.0559(15) Uani 1 1 d . . . H18 H 0.8922 0.5382 -0.0979 0.067 Uiso 1 1 calc R . . C19 C 0.8289(5) 0.6633(4) -0.0798(2) 0.0420(11) Uani 1 1 d . . . H19 H 0.8822 0.6868 -0.1199 0.050 Uiso 1 1 calc R . . C20 C 0.7448(4) 0.7181(3) -0.03471(19) 0.0324(9) Uani 1 1 d . . . H20 H 0.7392 0.7789 -0.0445 0.039 Uiso 1 1 calc R . . O1 O 0.5589(3) 0.82299(18) 0.05624(14) 0.0300(6) Uani 1 1 d . . . O2 O 0.4986(3) 0.71156(19) 0.12397(14) 0.0311(6) Uani 1 1 d . . . P1 P 0.15002(12) 0.57205(7) 0.28925(6) 0.0325(3) Uani 1 1 d . . . F1 F 0.2788(5) 0.5558(6) 0.3450(2) 0.153(3) Uani 1 1 d . . . F2 F 0.0089(4) 0.5771(3) 0.2284(2) 0.0844(13) Uani 1 1 d . . . F3 F 0.2743(4) 0.6124(2) 0.23478(19) 0.0656(9) Uani 1 1 d . . . F4 F 0.0166(4) 0.5358(2) 0.34077(19) 0.0652(9) Uani 1 1 d . . . F5 F 0.1044(6) 0.6655(3) 0.3158(3) 0.0956(15) Uani 1 1 d . . . F6 F 0.1815(6) 0.4776(3) 0.2592(3) 0.1145(19) 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 0.0204(2) 0.0326(3) 0.0174(2) -0.00357(17) 0.00156(16) -0.00143(17) N1 0.0229(14) 0.0351(17) 0.0256(15) 0.0095(13) 0.0003(11) 0.0022(12) N2 0.0326(16) 0.0233(15) 0.0237(14) -0.0042(11) 0.0078(12) -0.0037(12) N3 0.0244(17) 0.072(3) 0.0319(18) -0.0244(18) -0.0032(14) 0.0057(17) C1 0.0186(16) 0.0276(18) 0.0335(19) 0.0031(15) -0.0037(13) -0.0023(13) C2 0.0305(18) 0.0272(18) 0.0246(17) -0.0037(14) -0.0054(14) 0.0019(14) C3 0.037(2) 0.0278(18) 0.0161(15) 0.0001(13) -0.0011(13) 0.0046(15) C4 0.030(2) 0.048(3) 0.040(2) -0.0130(19) 0.0152(17) -0.0045(18) C5 0.0230(19) 0.052(3) 0.066(3) -0.026(2) 0.0123(19) -0.0086(18) C6 0.0205(18) 0.068(3) 0.049(3) -0.031(2) 0.0000(17) -0.0019(19) C7 0.037(2) 0.109(5) 0.022(2) -0.012(2) -0.0091(17) 0.019(3) C8 0.044(3) 0.098(4) 0.025(2) 0.018(2) -0.0019(18) 0.027(3) C9 0.042(2) 0.053(3) 0.033(2) 0.021(2) 0.0068(18) 0.011(2) C10 0.028(2) 0.029(2) 0.058(3) 0.0074(18) -0.0003(18) 0.0001(16) C11 0.036(2) 0.034(2) 0.0274(19) 0.0010(15) -0.0067(15) 0.0074(16) C12 0.067(3) 0.045(3) 0.0205(18) 0.0051(17) 0.0042(19) 0.013(2) C13 0.028(2) 0.099(5) 0.066(3) -0.060(3) -0.005(2) 0.003(2) C14 0.0205(16) 0.041(2) 0.0193(16) -0.0049(14) -0.0003(13) -0.0017(14) C15 0.0234(17) 0.046(2) 0.0216(17) -0.0054(15) 0.0006(13) 0.0017(16) C16 0.065(3) 0.051(3) 0.036(2) -0.003(2) 0.015(2) 0.013(2) C17 0.090(5) 0.057(3) 0.055(3) -0.008(3) 0.016(3) 0.028(3) C18 0.047(3) 0.084(4) 0.037(2) -0.023(3) 0.005(2) 0.025(3) C19 0.0219(18) 0.083(4) 0.0215(18) -0.010(2) 0.0024(14) 0.003(2) C20 0.0199(16) 0.055(3) 0.0219(17) -0.0058(16) -0.0009(13) 0.0013(16) O1 0.0281(13) 0.0381(15) 0.0240(13) 0.0009(11) 0.0032(10) 0.0032(11) O2 0.0336(14) 0.0363(15) 0.0238(13) -0.0049(11) 0.0098(11) -0.0029(12) P1 0.0266(5) 0.0303(5) 0.0412(6) 0.0053(4) 0.0104(4) -0.0062(4) F1 0.056(2) 0.348(10) 0.054(2) 0.047(4) -0.0033(19) 0.037(4) F2 0.053(2) 0.135(4) 0.065(2) 0.001(2) -0.0020(17) -0.027(2) F3 0.0457(17) 0.075(2) 0.077(2) 0.0114(18) 0.0210(16) -0.0133(16) F4 0.0453(17) 0.076(2) 0.075(2) 0.0175(18) 0.0155(15) -0.0021(16) F5 0.116(4) 0.067(3) 0.105(3) -0.032(2) 0.035(3) -0.017(2) F6 0.107(4) 0.069(3) 0.170(5) 0.008(3) 0.071(4) 0.017(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 1.988(3) . ? Ni1 N2 2.014(3) . ? Ni1 N3 2.044(3) . ? Ni1 O2 2.103(3) . ? Ni1 O1 2.103(3) . ? Ni1 C14 2.418(4) . ? N1 C1 1.276(5) . ? N1 C9 1.479(5) . ? N2 C4 1.497(5) . ? N2 C3 1.501(5) . ? N3 C6 1.495(5) . ? N3 C13 1.497(6) . ? N3 C7 1.500(7) . ? C1 C10 1.505(5) . ? C1 C2 1.506(5) . ? C2 C3 1.542(5) . ? C3 C11 1.528(6) . ? C3 C12 1.538(5) . ? C4 C5 1.527(6) . ? C5 C6 1.505(8) . ? C7 C8 1.507(9) . ? C8 C9 1.524(7) . ? C14 O1 1.262(5) . ? C14 O2 1.263(4) . ? C14 C15 1.501(5) . ? C15 C20 1.384(5) . ? C15 C16 1.386(7) . ? C16 C17 1.393(7) . ? C17 C18 1.374(8) . ? C18 C19 1.367(8) . ? C19 C20 1.388(6) . ? P1 F1 1.494(4) . ? P1 F5 1.564(4) . ? P1 F6 1.577(5) . ? P1 F4 1.580(3) . ? P1 F3 1.588(3) . ? P1 F2 1.614(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 N1 Ni1 N2 91.36(13) . . ? N1 Ni1 N3 94.43(15) . . ? N2 Ni1 N3 101.99(15) . . ? N1 Ni1 O2 157.00(12) . . ? N2 Ni1 O2 100.26(12) . . ? N3 Ni1 O2 102.36(14) . . ? N1 Ni1 O1 100.45(12) . . ? N2 Ni1 O1 158.39(13) . . ? N3 Ni1 O1 95.13(13) . . ? O2 Ni1 O1 62.81(10) . . ? N1 Ni1 C14 130.86(13) . . ? N2 Ni1 C14 131.07(13) . . ? N3 Ni1 C14 98.36(13) . . ? O2 Ni1 C14 31.48(12) . . ? O1 Ni1 C14 31.43(12) . . ? C1 N1 C9 120.7(4) . . ? C1 N1 Ni1 128.3(3) . . ? C9 N1 Ni1 111.0(3) . . ? C4 N2 C3 115.2(3) . . ? C4 N2 Ni1 116.0(3) . . ? C3 N2 Ni1 104.7(2) . . ? C6 N3 C13 108.2(4) . . ? C6 N3 C7 109.2(4) . . ? C13 N3 C7 107.8(4) . . ? C6 N3 Ni1 113.3(3) . . ? C13 N3 Ni1 108.9(3) . . ? C7 N3 Ni1 109.2(3) . . ? N1 C1 C10 124.9(4) . . ? N1 C1 C2 121.5(3) . . ? C10 C1 C2 113.7(3) . . ? C1 C2 C3 120.6(3) . . ? N2 C3 C11 106.7(3) . . ? N2 C3 C12 111.0(3) . . ? C11 C3 C12 109.8(3) . . ? N2 C3 C2 111.1(3) . . ? C11 C3 C2 110.2(3) . . ? C12 C3 C2 108.1(3) . . ? N2 C4 C5 111.3(3) . . ? C6 C5 C4 113.5(4) . . ? N3 C6 C5 114.9(4) . . ? N3 C7 C8 116.1(4) . . ? C7 C8 C9 116.3(4) . . ? N1 C9 C8 111.5(4) . . ? O1 C14 O2 120.4(3) . . ? O1 C14 C15 119.5(3) . . ? O2 C14 C15 120.0(4) . . ? O1 C14 Ni1 60.36(19) . . ? O2 C14 Ni1 60.36(19) . . ? C15 C14 Ni1 171.5(3) . . ? C20 C15 C16 119.6(4) . . ? C20 C15 C14 120.2(4) . . ? C16 C15 C14 120.1(4) . . ? C15 C16 C17 119.4(5) . . ? C18 C17 C16 120.5(6) . . ? C19 C18 C17 120.1(4) . . ? C18 C19 C20 120.2(4) . . ? C15 C20 C19 120.2(4) . . ? C14 O1 Ni1 88.2(2) . . ? C14 O2 Ni1 88.2(2) . . ? F1 P1 F5 95.8(4) . . ? F1 P1 F6 88.8(4) . . ? F5 P1 F6 175.1(3) . . ? F1 P1 F4 90.4(2) . . ? F5 P1 F4 87.2(2) . . ? F6 P1 F4 91.0(2) . . ? F1 P1 F3 93.3(2) . . ? F5 P1 F3 90.7(2) . . ? F6 P1 F3 90.8(2) . . ? F4 P1 F3 176.0(2) . . ? F1 P1 F2 173.2(4) . . ? F5 P1 F2 90.4(3) . . ? F6 P1 F2 85.0(3) . . ? F4 P1 F2 87.14(19) . . ? F3 P1 F2 89.5(2) . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 0.50 _diffrn_measured_fraction_theta_full 0.000 _refine_diff_density_max 1.440 _refine_diff_density_min -0.895 _refine_diff_density_rms 0.108 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 249397' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H32 N3 Ni O3, F6 P' _chemical_formula_sum 'C20 H32 F6 N3 Ni O3 P' _chemical_formula_weight 566.17 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 P21cn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, y+1/2, -z+1/2' 'x+1/2, -y, -z' 'x, -y+1/2, z+1/2' _cell_length_a 8.3340(11) _cell_length_b 15.805(2) _cell_length_c 18.376(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2420.5(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 blue _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.941 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8414 _exptl_absorpt_correction_T_max 0.9035 _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 'Bruker APEX' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14681 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 28.18 _reflns_number_total 4784 _reflns_number_gt 4537 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WinGX publication routines (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. ; _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^)+(0.0616P)^2^+2.2033P] 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 0.05(2) _refine_ls_number_reflns 4784 _refine_ls_number_parameters 309 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1253 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _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 0.05679(8) 0.81072(3) 0.12994(2) 0.01908(13) Uani 1 1 d . . . N1 N 0.0918(4) 0.9341(2) 0.12717(18) 0.0251(8) Uani 1 1 d . . . N2 N 0.1235(5) 0.8009(2) 0.23453(19) 0.0231(7) Uani 1 1 d . . . H2 H 0.0910 0.7473 0.2493 0.028 Uiso 1 1 calc R . . N3 N 0.2615(5) 0.7789(2) 0.07675(19) 0.0222(7) Uani 1 1 d . . . C1 C 0.0861(5) 0.9848(3) 0.1807(2) 0.0257(9) Uani 1 1 d . . . C2 C 0.0643(7) 0.9550(2) 0.2579(2) 0.0306(9) Uani 1 1 d . . . H2A H -0.0191 0.9913 0.2802 0.037 Uiso 1 1 calc R . . H2B H 0.1657 0.9671 0.2840 0.037 Uiso 1 1 calc R . . C3 C 0.0187(6) 0.8620(3) 0.2754(2) 0.0308(11) Uani 1 1 d . . . C4 C 0.2977(6) 0.8057(3) 0.2515(3) 0.0261(10) Uani 1 1 d . . . H4A H 0.3162 0.7845 0.3015 0.031 Uiso 1 1 calc R . . H4B H 0.3325 0.8656 0.2498 0.031 Uiso 1 1 calc R . . C5 C 0.3973(5) 0.7548(3) 0.1989(2) 0.0252(9) Uani 1 1 d . . . H5A H 0.3510 0.6973 0.1951 0.030 Uiso 1 1 calc R . . H5B H 0.5071 0.7492 0.2188 0.030 Uiso 1 1 calc R . . C6 C 0.4077(6) 0.7929(3) 0.1231(2) 0.0254(9) Uani 1 1 d . . . H6A H 0.4262 0.8545 0.1278 0.030 Uiso 1 1 calc R . . H6B H 0.5019 0.7684 0.0979 0.030 Uiso 1 1 calc R . . C7 C 0.2739(6) 0.8322(3) 0.0097(3) 0.0309(10) Uani 1 1 d . . . H7A H 0.1835 0.8176 -0.0229 0.037 Uiso 1 1 calc R . . H7B H 0.3743 0.8170 -0.0160 0.037 Uiso 1 1 calc R . . C8 C 0.2729(6) 0.9276(3) 0.0215(2) 0.0286(10) Uani 1 1 d . . . H8A H 0.3615 0.9423 0.0551 0.034 Uiso 1 1 calc R . . H8B H 0.2955 0.9555 -0.0257 0.034 Uiso 1 1 calc R . . C9 C 0.1178(6) 0.9637(3) 0.0519(2) 0.0285(10) Uani 1 1 d . . . H9A H 0.1229 1.0263 0.0513 0.034 Uiso 1 1 calc R . . H9B H 0.0266 0.9459 0.0210 0.034 Uiso 1 1 calc R . . C10 C 0.1042(6) 1.0796(3) 0.1758(3) 0.0338(11) Uani 1 1 d . . . H10A H 0.2017 1.0934 0.1484 0.051 Uiso 1 1 calc R . . H10B H 0.1119 1.1035 0.2249 0.051 Uiso 1 1 calc R . . H10C H 0.0108 1.1037 0.1509 0.051 Uiso 1 1 calc R . . C11 C 0.0335(8) 0.8493(3) 0.3578(2) 0.0376(12) Uani 1 1 d . . . H11A H 0.0047 0.7909 0.3702 0.056 Uiso 1 1 calc R . . H11B H -0.0390 0.8884 0.3829 0.056 Uiso 1 1 calc R . . H11C H 0.1443 0.8604 0.3730 0.056 Uiso 1 1 calc R . . C12 C -0.1539(6) 0.8437(3) 0.2515(3) 0.0320(11) Uani 1 1 d . . . H12A H -0.1634 0.8520 0.1988 0.048 Uiso 1 1 calc R . . H12B H -0.2274 0.8822 0.2767 0.048 Uiso 1 1 calc R . . H12C H -0.1815 0.7851 0.2636 0.048 Uiso 1 1 calc R . . C13 C 0.2566(7) 0.6905(3) 0.0538(3) 0.0320(11) Uani 1 1 d . . . H13A H 0.2478 0.6539 0.0967 0.048 Uiso 1 1 calc R . . H13B H 0.3551 0.6767 0.0272 0.048 Uiso 1 1 calc R . . H13C H 0.1636 0.6814 0.0221 0.048 Uiso 1 1 calc R . . C14 C -0.1409(6) 0.7282(3) 0.0622(2) 0.0244(9) Uani 1 1 d . . . C15 C -0.2512(6) 0.6754(3) 0.0193(2) 0.0249(9) Uani 1 1 d . . . C16 C -0.3105(6) 0.7066(4) -0.0472(3) 0.0356(11) Uani 1 1 d . . . H16 H -0.2839 0.7620 -0.0630 0.043 Uiso 1 1 calc R . . C17 C -0.4095(6) 0.6545(4) -0.0897(2) 0.0433(14) Uani 1 1 d . . . H17 H -0.4541 0.6756 -0.1338 0.052 Uiso 1 1 calc R . . C18 C -0.4421(8) 0.5733(4) -0.0679(3) 0.0472(13) Uani 1 1 d . . . H18 H -0.5023 0.5372 -0.0990 0.057 Uiso 1 1 calc R . . C19 C -0.3895(7) 0.5432(3) -0.0020(3) 0.0437(13) Uani 1 1 d . . . H19 H -0.4189 0.4881 0.0137 0.052 Uiso 1 1 calc R . . C20 C -0.2923(6) 0.5942(3) 0.0419(3) 0.0306(10) Uani 1 1 d . . . O1 O -0.1001(4) 0.80092(19) 0.04179(18) 0.0300(7) Uani 1 1 d . . . O2 O -0.0826(4) 0.70052(18) 0.12164(15) 0.0254(7) Uani 1 1 d . . . O3 O -0.2413(6) 0.5636(2) 0.1061(2) 0.0505(10) Uani 1 1 d . . . H3 H -0.1999 0.6028 0.1306 0.076 Uiso 1 1 calc R . . P1 P 0.09062(15) 0.56162(7) 0.30605(6) 0.0273(3) Uani 1 1 d . . . F5 F 0.2124(4) 0.49837(18) 0.34534(16) 0.0416(7) Uani 1 1 d . . . F1 F 0.2015(4) 0.63995(18) 0.33227(17) 0.0401(7) Uani 1 1 d . . . F4 F -0.0077(4) 0.5699(2) 0.38039(17) 0.0505(9) Uani 1 1 d . . . F3 F 0.1929(5) 0.5574(2) 0.23317(17) 0.0534(9) Uani 1 1 d . . . F6 F -0.0296(4) 0.62736(19) 0.26853(17) 0.0444(8) Uani 1 1 d . . . F2 F -0.0187(5) 0.4861(2) 0.2810(2) 0.0644(11) 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 0.0182(2) 0.0201(2) 0.0190(2) 0.00387(17) -0.0010(2) -0.0022(2) N1 0.023(2) 0.0248(17) 0.0273(17) 0.0064(13) -0.0014(15) 0.0027(14) N2 0.0250(19) 0.0211(16) 0.0233(18) 0.0039(13) 0.0036(15) -0.0030(15) N3 0.0198(19) 0.0248(18) 0.0220(18) 0.0008(14) 0.0009(14) 0.0013(15) C1 0.017(2) 0.0229(19) 0.037(2) -0.0001(16) 0.0018(17) 0.0041(17) C2 0.034(2) 0.0243(19) 0.034(2) -0.0076(15) 0.003(2) -0.005(2) C3 0.042(3) 0.027(2) 0.023(2) -0.0011(16) 0.0100(18) -0.003(2) C4 0.026(2) 0.027(2) 0.025(2) 0.0080(17) -0.0009(18) -0.0084(18) C5 0.016(2) 0.024(2) 0.036(2) 0.0042(17) -0.0104(17) 0.0015(17) C6 0.022(2) 0.024(2) 0.030(2) -0.0016(16) 0.0025(18) 0.0015(18) C7 0.025(3) 0.044(3) 0.024(2) -0.0025(19) 0.0007(18) 0.000(2) C8 0.026(2) 0.036(2) 0.024(2) 0.0114(18) -0.0027(18) -0.005(2) C9 0.035(3) 0.0227(19) 0.028(2) 0.0152(17) -0.0058(18) -0.0007(19) C10 0.028(3) 0.024(2) 0.050(3) 0.0019(19) 0.007(2) 0.0001(19) C11 0.044(4) 0.052(3) 0.017(2) -0.0010(18) 0.005(2) -0.011(3) C12 0.032(3) 0.035(3) 0.029(2) -0.0005(19) 0.012(2) 0.000(2) C13 0.031(3) 0.030(3) 0.035(3) -0.0048(19) 0.002(2) 0.000(2) C14 0.019(2) 0.031(2) 0.023(2) 0.0042(17) 0.0026(17) -0.0001(19) C15 0.018(2) 0.033(2) 0.023(2) -0.0037(17) 0.0039(17) 0.0008(18) C16 0.020(2) 0.057(3) 0.030(2) 0.004(2) 0.0034(18) 0.001(2) C17 0.023(3) 0.088(4) 0.020(2) -0.009(2) 0.0009(17) 0.004(3) C18 0.027(3) 0.072(4) 0.042(3) -0.027(2) 0.000(3) -0.014(3) C19 0.040(3) 0.039(3) 0.052(3) -0.020(2) 0.006(2) -0.009(2) C20 0.028(2) 0.030(2) 0.034(2) -0.0019(18) 0.0059(19) -0.001(2) O1 0.0305(19) 0.0283(16) 0.0311(18) 0.0069(13) -0.0061(14) -0.0025(14) O2 0.0314(19) 0.0254(15) 0.0195(15) 0.0052(11) -0.0067(12) -0.0034(14) O3 0.055(3) 0.037(2) 0.059(3) 0.0056(18) -0.003(2) -0.005(2) P1 0.0281(7) 0.0252(5) 0.0286(5) 0.0063(4) -0.0025(4) -0.0047(5) F5 0.051(2) 0.0304(14) 0.0433(16) 0.0009(12) -0.0085(15) 0.0059(14) F1 0.0375(18) 0.0350(15) 0.0479(17) 0.0009(12) -0.0048(14) -0.0051(13) F4 0.0384(19) 0.074(2) 0.0394(18) 0.0187(15) 0.0061(13) 0.0089(17) F3 0.057(2) 0.069(2) 0.0349(17) -0.0026(15) 0.0064(15) -0.0026(18) F6 0.0383(18) 0.0442(17) 0.0508(19) 0.0231(14) -0.0118(14) -0.0059(14) F2 0.077(3) 0.0442(19) 0.072(2) 0.0129(17) -0.035(2) -0.0307(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 1.972(4) . ? Ni1 N2 2.007(4) . ? Ni1 N3 2.029(4) . ? Ni1 O1 2.087(3) . ? Ni1 O2 2.099(3) . ? Ni1 C14 2.443(5) . ? N1 C1 1.270(6) . ? N1 C9 1.476(5) . ? N2 C4 1.487(6) . ? N2 C3 1.503(6) . ? N3 C13 1.461(6) . ? N3 C7 1.497(6) . ? N3 C6 1.504(6) . ? C1 C2 1.506(6) . ? C1 C10 1.509(6) . ? C2 C3 1.552(6) . ? C3 C12 1.532(7) . ? C3 C11 1.533(6) . ? C4 C5 1.506(7) . ? C5 C6 1.519(6) . ? C7 C8 1.523(7) . ? C8 C9 1.520(7) . ? C14 O1 1.256(5) . ? C14 O2 1.273(5) . ? C14 C15 1.470(6) . ? C15 C20 1.392(6) . ? C15 C16 1.407(7) . ? C16 C17 1.403(7) . ? C17 C18 1.372(8) . ? C18 C19 1.373(8) . ? C19 C20 1.398(7) . ? C20 O3 1.345(6) . ? P1 F2 1.571(3) . ? P1 F3 1.589(3) . ? P1 F5 1.597(3) . ? P1 F4 1.598(3) . ? P1 F6 1.599(3) . ? P1 F1 1.619(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N2 93.47(14) . . ? N1 Ni1 N3 96.19(15) . . ? N2 Ni1 N3 102.08(15) . . ? N1 Ni1 O1 98.40(13) . . ? N2 Ni1 O1 155.64(15) . . ? N3 Ni1 O1 97.72(15) . . ? N1 Ni1 O2 154.21(14) . . ? N2 Ni1 O2 99.12(13) . . ? N3 Ni1 O2 102.99(14) . . ? O1 Ni1 O2 62.32(12) . . ? N1 Ni1 C14 127.93(15) . . ? N2 Ni1 C14 129.31(14) . . ? N3 Ni1 C14 100.92(16) . . ? O1 Ni1 C14 30.95(13) . . ? O2 Ni1 C14 31.41(13) . . ? C1 N1 C9 122.0(4) . . ? C1 N1 Ni1 126.8(3) . . ? C9 N1 Ni1 111.1(3) . . ? C4 N2 C3 115.4(4) . . ? C4 N2 Ni1 117.8(3) . . ? C3 N2 Ni1 105.5(3) . . ? C13 N3 C7 107.6(4) . . ? C13 N3 C6 109.1(4) . . ? C7 N3 C6 109.2(3) . . ? C13 N3 Ni1 110.6(3) . . ? C7 N3 Ni1 108.4(3) . . ? C6 N3 Ni1 111.8(3) . . ? N1 C1 C2 122.5(4) . . ? N1 C1 C10 125.3(4) . . ? C2 C1 C10 112.2(4) . . ? C1 C2 C3 121.4(3) . . ? N2 C3 C12 106.3(4) . . ? N2 C3 C11 111.3(4) . . ? C12 C3 C11 109.5(4) . . ? N2 C3 C2 111.3(4) . . ? C12 C3 C2 110.4(4) . . ? C11 C3 C2 108.0(4) . . ? N2 C4 C5 112.1(4) . . ? C4 C5 C6 114.1(4) . . ? N3 C6 C5 114.5(4) . . ? N3 C7 C8 116.1(4) . . ? C9 C8 C7 115.4(4) . . ? N1 C9 C8 110.5(3) . . ? O1 C14 O2 117.8(4) . . ? O1 C14 C15 121.9(4) . . ? O2 C14 C15 120.2(4) . . ? O1 C14 Ni1 58.7(2) . . ? O2 C14 Ni1 59.2(2) . . ? C15 C14 Ni1 176.3(3) . . ? C20 C15 C16 119.7(4) . . ? C20 C15 C14 121.2(4) . . ? C16 C15 C14 119.1(4) . . ? C15 C16 C17 119.0(5) . . ? C18 C17 C16 120.1(5) . . ? C17 C18 C19 121.3(5) . . ? C18 C19 C20 119.6(5) . . ? O3 C20 C15 121.0(4) . . ? O3 C20 C19 118.8(5) . . ? C15 C20 C19 120.2(5) . . ? C14 O1 Ni1 90.3(3) . . ? C14 O2 Ni1 89.4(3) . . ? F2 P1 F3 91.8(2) . . ? F2 P1 F5 91.47(19) . . ? F3 P1 F5 90.77(19) . . ? F2 P1 F4 90.9(2) . . ? F3 P1 F4 177.2(2) . . ? F5 P1 F4 89.47(18) . . ? F2 P1 F6 90.23(19) . . ? F3 P1 F6 90.01(18) . . ? F5 P1 F6 178.11(18) . . ? F4 P1 F6 89.66(18) . . ? F2 P1 F1 179.4(2) . . ? F3 P1 F1 88.67(18) . . ? F5 P1 F1 88.92(17) . . ? F4 P1 F1 88.59(19) . . ? F6 P1 F1 89.38(16) . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 0.50 _diffrn_measured_fraction_theta_full 0.000 _refine_diff_density_max 0.890 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.100 #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 249398' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H34 N3 Ni O4, F6 P, H2 O' _chemical_formula_sum 'C22 H36 F6 N3 Ni O5 P' _chemical_formula_weight 626.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.2175(4) _cell_length_b 15.2313(8) _cell_length_c 10.7289(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.8200(10) _cell_angle_gamma 90.00 _cell_volume 1326.98(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6285 _cell_measurement_theta_min 2.508 _cell_measurement_theta_max 27.978 _exptl_crystal_description Block _exptl_crystal_colour Blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 0.872 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7677 _exptl_absorpt_correction_T_max 0.8877 _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 'Bruker APEX' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15098 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28.13 _reflns_number_total 5943 _reflns_number_gt 5813 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WinGX publication routines (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. ; _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^)+(0.0700P)^2^+0.9715P] 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 0.038(12) _refine_ls_number_reflns 5943 _refine_ls_number_parameters 345 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.018 _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 0.02719(4) 0.57994(2) 0.24940(3) 0.01713(10) Uani 1 1 d . . . N1 N 0.0233(3) 0.44984(19) 0.2514(3) 0.0222(6) Uani 1 1 d . . . N2 N 0.1725(3) 0.5878(2) 0.4186(2) 0.0195(5) Uani 1 1 d . . . H2 H 0.1646 0.6455 0.4454 0.023 Uiso 1 1 calc R . . N3 N 0.1893(3) 0.5887(2) 0.1237(2) 0.0225(5) Uani 1 1 d . . . C1 C 0.0579(4) 0.39932(19) 0.3472(3) 0.0214(6) Uani 1 1 d . . . C2 C 0.1058(4) 0.4339(2) 0.4791(3) 0.0238(6) Uani 1 1 d . . . H2A H 0.2221 0.4171 0.5071 0.029 Uiso 1 1 calc R . . H2B H 0.0391 0.4020 0.5338 0.029 Uiso 1 1 calc R . . C3 C 0.0906(4) 0.5326(2) 0.5069(3) 0.0223(6) Uani 1 1 d . . . C4 C 0.3515(3) 0.5707(2) 0.4214(3) 0.0237(6) Uani 1 1 d . . . H4A H 0.3704 0.5066 0.4211 0.028 Uiso 1 1 calc R . . H4B H 0.4132 0.5947 0.5006 0.028 Uiso 1 1 calc R . . C5 C 0.4172(4) 0.6116(2) 0.3099(3) 0.0243(6) Uani 1 1 d . . . H5A H 0.5390 0.6105 0.3270 0.029 Uiso 1 1 calc R . . H5B H 0.3825 0.6739 0.3031 0.029 Uiso 1 1 calc R . . C6 C 0.3608(4) 0.5668(2) 0.1832(3) 0.0235(7) Uani 1 1 d . . . H6A H 0.4371 0.5834 0.1242 0.028 Uiso 1 1 calc R . . H6B H 0.3690 0.5024 0.1955 0.028 Uiso 1 1 calc R . . C7 C 0.1389(4) 0.5297(3) 0.0146(3) 0.0293(7) Uani 1 1 d . . . H7A H 0.2233 0.5334 -0.0419 0.035 Uiso 1 1 calc R . . H7B H 0.0344 0.5522 -0.0329 0.035 Uiso 1 1 calc R . . C8 C 0.1147(4) 0.4333(3) 0.0452(3) 0.0301(7) Uani 1 1 d . . . H8A H 0.2195 0.4104 0.0916 0.036 Uiso 1 1 calc R . . H8B H 0.0908 0.4003 -0.0350 0.036 Uiso 1 1 calc R . . C9 C -0.0221(4) 0.4146(2) 0.1230(3) 0.0285(7) Uani 1 1 d . . . H9A H -0.1259 0.4420 0.0822 0.034 Uiso 1 1 calc R . . H9B H -0.0402 0.3504 0.1271 0.034 Uiso 1 1 calc R . . C10 C 0.0576(4) 0.3000(2) 0.3411(4) 0.0315(7) Uani 1 1 d . . . H10A H 0.1216 0.2807 0.2762 0.047 Uiso 1 1 calc R . . H10B H -0.0559 0.2788 0.3202 0.047 Uiso 1 1 calc R . . H10C H 0.1071 0.2762 0.4231 0.047 Uiso 1 1 calc R . . C11 C -0.0924(4) 0.5595(2) 0.4878(3) 0.0251(7) Uani 1 1 d . . . H11A H -0.1416 0.5486 0.4001 0.038 Uiso 1 1 calc R . . H11B H -0.1013 0.6221 0.5070 0.038 Uiso 1 1 calc R . . H11C H -0.1505 0.5250 0.5443 0.038 Uiso 1 1 calc R . . C12 C 0.1657(5) 0.5496(3) 0.6453(3) 0.0330(8) Uani 1 1 d . . . H12A H 0.2822 0.5327 0.6584 0.050 Uiso 1 1 calc R . . H12B H 0.1068 0.5147 0.7008 0.050 Uiso 1 1 calc R . . H12C H 0.1560 0.6120 0.6646 0.050 Uiso 1 1 calc R . . C13 C 0.1884(4) 0.6799(3) 0.0718(4) 0.0309(8) Uani 1 1 d . . . H13A H 0.2209 0.7215 0.1408 0.046 Uiso 1 1 calc R . . H13B H 0.0774 0.6944 0.0293 0.046 Uiso 1 1 calc R . . H13C H 0.2661 0.6836 0.0113 0.046 Uiso 1 1 calc R . . O1 O -0.1889(3) 0.60884(15) 0.1202(2) 0.0248(5) Uani 1 1 d . . . O2 O -0.0698(3) 0.70563(15) 0.2564(2) 0.0243(5) Uani 1 1 d . . . C14 C -0.1862(4) 0.6842(2) 0.1671(3) 0.0197(6) Uani 1 1 d . . . C15 C -0.3147(4) 0.7513(2) 0.1244(3) 0.0191(6) Uani 1 1 d . . . C16 C -0.3852(5) 0.7599(2) -0.0013(3) 0.0278(7) Uani 1 1 d . . . C17 C -0.5012(4) 0.8254(2) -0.0375(3) 0.0273(7) Uani 1 1 d . . . H17 H -0.5499 0.8310 -0.1234 0.033 Uiso 1 1 calc R . . C18 C -0.5447(4) 0.8820(3) 0.0519(4) 0.0309(8) Uani 1 1 d . . . H18 H -0.6193 0.9287 0.0268 0.037 Uiso 1 1 calc R . . C19 C -0.4814(5) 0.8718(3) 0.1767(4) 0.0399(9) Uani 1 1 d . . . H19 H -0.5184 0.9079 0.2387 0.048 Uiso 1 1 calc R . . C20 C -0.3619(5) 0.8077(3) 0.2119(3) 0.0324(8) Uani 1 1 d . . . H20 H -0.3126 0.8030 0.2977 0.039 Uiso 1 1 calc R . . C21 C -0.3895(5) 0.6407(2) -0.1406(4) 0.0328(8) Uani 1 1 d . . . C22 C -0.3071(5) 0.5979(2) -0.2349(4) 0.0348(8) Uani 1 1 d . . . H22A H -0.2099 0.6321 -0.2474 0.052 Uiso 1 1 calc R . . H22B H -0.3829 0.5941 -0.3147 0.052 Uiso 1 1 calc R . . H22C H -0.2731 0.5387 -0.2061 0.052 Uiso 1 1 calc R . . O3 O -0.3131(3) 0.71478(19) -0.0956(2) 0.0332(6) Uani 1 1 d . . . O4 O -0.5137(4) 0.61366(19) -0.1061(3) 0.0379(6) Uani 1 1 d . . . P1 P 0.41641(10) 0.82179(5) 0.56806(8) 0.02292(18) Uani 1 1 d . . . F1 F 0.4319(4) 0.89879(17) 0.4687(2) 0.0456(7) Uani 1 1 d . . . F2 F 0.3995(3) 0.74337(15) 0.6651(2) 0.0363(5) Uani 1 1 d . . . F3 F 0.5397(3) 0.76218(18) 0.5020(2) 0.0435(6) Uani 1 1 d . . . F4 F 0.5722(2) 0.86035(14) 0.6615(2) 0.0312(4) Uani 1 1 d . . . F5 F 0.2991(3) 0.88136(15) 0.6363(2) 0.0387(5) Uani 1 1 d . . . F6 F 0.2618(3) 0.78196(16) 0.4759(2) 0.0389(5) Uani 1 1 d . . . O5 O 0.0944(6) 0.8781(3) 0.2553(4) 0.0769(12) Uani 1 1 d . . . H23 H 0.0360 0.8236 0.2655 0.092 Uiso 1 1 d . . . H24 H 0.1842 0.8719 0.3207 0.092 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 0.01619(16) 0.01590(17) 0.01885(17) -0.00008(15) 0.00127(12) 0.00042(16) N1 0.0132(12) 0.0217(14) 0.0315(15) -0.0067(10) 0.0025(10) -0.0009(10) N2 0.0206(11) 0.0155(12) 0.0215(11) -0.0007(11) 0.0004(9) -0.0006(11) N3 0.0197(11) 0.0264(14) 0.0213(11) 0.0019(12) 0.0022(9) -0.0007(12) C1 0.0167(13) 0.0125(13) 0.0358(17) -0.0034(12) 0.0059(12) -0.0013(10) C2 0.0240(15) 0.0194(15) 0.0286(16) 0.0050(12) 0.0054(12) 0.0010(12) C3 0.0288(16) 0.0186(16) 0.0195(14) 0.0013(11) 0.0035(12) 0.0016(12) C4 0.0177(13) 0.0248(16) 0.0266(14) 0.0014(13) -0.0028(10) -0.0041(13) C5 0.0172(14) 0.0231(14) 0.0319(17) -0.0003(12) 0.0015(12) -0.0039(11) C6 0.0171(12) 0.0266(19) 0.0272(14) 0.0005(12) 0.0051(11) 0.0015(12) C7 0.0252(16) 0.044(2) 0.0183(14) -0.0035(14) 0.0022(12) 0.0012(14) C8 0.0266(16) 0.0375(19) 0.0259(16) -0.0133(14) 0.0031(13) 0.0012(14) C9 0.0239(15) 0.0279(17) 0.0318(17) -0.0092(14) -0.0019(13) -0.0009(13) C10 0.0263(16) 0.0157(15) 0.052(2) -0.0011(14) 0.0046(15) 0.0014(12) C11 0.0254(15) 0.0215(17) 0.0307(16) -0.0031(12) 0.0116(13) 0.0029(11) C12 0.042(2) 0.0350(18) 0.0212(16) 0.0011(13) 0.0015(14) -0.0006(15) C13 0.0259(16) 0.0342(19) 0.0348(18) 0.0147(15) 0.0114(14) 0.0036(14) O1 0.0240(11) 0.0216(11) 0.0271(12) -0.0007(9) -0.0015(9) 0.0047(8) O2 0.0277(11) 0.0194(11) 0.0229(11) -0.0030(8) -0.0056(9) 0.0055(9) C14 0.0191(13) 0.0190(14) 0.0211(14) 0.0030(11) 0.0036(11) 0.0011(11) C15 0.0171(13) 0.0191(14) 0.0208(14) 0.0031(11) 0.0020(11) -0.0001(11) C16 0.0343(18) 0.0231(16) 0.0244(16) -0.0025(13) -0.0008(14) 0.0038(13) C17 0.0294(16) 0.0254(16) 0.0249(16) -0.0006(14) -0.0027(14) 0.0047(14) C18 0.0221(16) 0.0335(19) 0.0351(19) -0.0014(15) -0.0022(14) 0.0113(14) C19 0.041(2) 0.044(2) 0.0331(19) -0.0132(17) -0.0003(16) 0.0214(18) C20 0.0349(18) 0.039(2) 0.0219(15) -0.0052(14) -0.0015(13) 0.0147(16) C21 0.042(2) 0.0300(18) 0.0275(17) 0.0013(14) 0.0080(16) 0.0064(15) C22 0.0375(19) 0.030(2) 0.0360(18) -0.0105(14) 0.0030(15) -0.0005(14) O3 0.0301(13) 0.0414(15) 0.0299(12) 0.0048(11) 0.0102(10) -0.0029(11) O4 0.0367(14) 0.0342(14) 0.0449(16) -0.0019(12) 0.0132(12) -0.0077(11) P1 0.0220(4) 0.0230(4) 0.0235(4) -0.0049(3) 0.0027(3) -0.0054(3) F1 0.0618(17) 0.0402(14) 0.0316(12) 0.0076(10) -0.0027(11) -0.0176(12) F2 0.0401(12) 0.0305(11) 0.0366(12) 0.0041(9) 0.0010(10) -0.0048(9) F3 0.0342(13) 0.0550(16) 0.0430(14) -0.0244(12) 0.0112(11) -0.0036(11) F4 0.0244(10) 0.0354(11) 0.0327(11) -0.0089(9) 0.0007(8) -0.0059(8) F5 0.0314(11) 0.0352(12) 0.0500(14) -0.0082(10) 0.0082(10) 0.0044(9) F6 0.0309(11) 0.0362(12) 0.0443(13) -0.0051(10) -0.0111(10) -0.0100(9) O5 0.092(3) 0.065(3) 0.068(3) 0.001(2) -0.003(2) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 1.982(3) . ? Ni1 N2 2.017(2) . ? Ni1 N3 2.040(2) . ? Ni1 O2 2.079(2) . ? Ni1 O1 2.124(2) . ? Ni1 C14 2.430(3) . ? N1 C1 1.280(5) . ? N1 C9 1.472(4) . ? N2 C4 1.489(4) . ? N2 C3 1.501(4) . ? N3 C7 1.483(4) . ? N3 C6 1.493(4) . ? N3 C13 1.497(5) . ? C1 C2 1.505(5) . ? C1 C10 1.514(4) . ? C2 C3 1.542(4) . ? C3 C12 1.540(5) . ? C3 C11 1.541(4) . ? C4 C5 1.519(4) . ? C5 C6 1.529(5) . ? C7 C8 1.525(6) . ? C8 C9 1.526(5) . ? O1 C14 1.252(4) . ? O2 C14 1.288(4) . ? C14 C15 1.490(4) . ? C15 C20 1.371(5) . ? C15 C16 1.390(5) . ? C16 C17 1.394(5) . ? C16 O3 1.426(4) . ? C17 C18 1.377(5) . ? C18 C19 1.369(6) . ? C19 C20 1.394(5) . ? C21 O4 1.210(5) . ? C21 O3 1.345(5) . ? C21 C22 1.455(5) . ? P1 F5 1.582(2) . ? P1 F1 1.603(3) . ? P1 F3 1.604(2) . ? P1 F6 1.605(2) . ? P1 F2 1.605(2) . ? P1 F4 1.611(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 N1 Ni1 N2 93.32(12) . . ? N1 Ni1 N3 94.91(12) . . ? N2 Ni1 N3 103.54(10) . . ? N1 Ni1 O2 155.96(12) . . ? N2 Ni1 O2 95.18(10) . . ? N3 Ni1 O2 104.85(12) . . ? N1 Ni1 O1 101.60(10) . . ? N2 Ni1 O1 153.50(10) . . ? N3 Ni1 O1 96.93(10) . . ? O2 Ni1 O1 63.00(9) . . ? N1 Ni1 C14 130.22(11) . . ? N2 Ni1 C14 125.67(11) . . ? N3 Ni1 C14 103.00(11) . . ? O2 Ni1 C14 32.01(10) . . ? O1 Ni1 C14 31.00(10) . . ? C1 N1 C9 121.7(3) . . ? C1 N1 Ni1 127.4(2) . . ? C9 N1 Ni1 110.9(2) . . ? C4 N2 C3 115.3(3) . . ? C4 N2 Ni1 117.03(18) . . ? C3 N2 Ni1 105.88(18) . . ? C7 N3 C6 109.4(3) . . ? C7 N3 C13 106.5(3) . . ? C6 N3 C13 108.5(3) . . ? C7 N3 Ni1 110.5(2) . . ? C6 N3 Ni1 111.87(18) . . ? C13 N3 Ni1 109.9(2) . . ? N1 C1 C2 122.6(3) . . ? N1 C1 C10 124.6(3) . . ? C2 C1 C10 112.9(3) . . ? C1 C2 C3 120.4(3) . . ? N2 C3 C12 111.3(3) . . ? N2 C3 C11 106.9(2) . . ? C12 C3 C11 108.8(3) . . ? N2 C3 C2 111.5(3) . . ? C12 C3 C2 108.5(3) . . ? C11 C3 C2 109.9(3) . . ? N2 C4 C5 112.4(3) . . ? C4 C5 C6 114.9(3) . . ? N3 C6 C5 114.7(3) . . ? N3 C7 C8 116.3(3) . . ? C7 C8 C9 115.4(3) . . ? N1 C9 C8 109.9(3) . . ? C14 O1 Ni1 88.08(18) . . ? C14 O2 Ni1 89.14(18) . . ? O1 C14 O2 119.8(3) . . ? O1 C14 C15 122.5(3) . . ? O2 C14 C15 117.7(3) . . ? O1 C14 Ni1 60.92(16) . . ? O2 C14 Ni1 58.85(15) . . ? C15 C14 Ni1 176.3(2) . . ? C20 C15 C16 119.0(3) . . ? C20 C15 C14 118.8(3) . . ? C16 C15 C14 122.2(3) . . ? C15 C16 C17 120.3(3) . . ? C15 C16 O3 119.1(3) . . ? C17 C16 O3 119.2(3) . . ? C18 C17 C16 119.5(3) . . ? C19 C18 C17 120.6(3) . . ? C18 C19 C20 119.4(3) . . ? C15 C20 C19 121.0(3) . . ? O4 C21 O3 123.0(3) . . ? O4 C21 C22 124.4(4) . . ? O3 C21 C22 112.6(3) . . ? C21 O3 C16 115.9(3) . . ? F5 P1 F1 90.24(15) . . ? F5 P1 F3 178.33(14) . . ? F1 P1 F3 90.00(16) . . ? F5 P1 F6 91.20(13) . . ? F1 P1 F6 90.17(14) . . ? F3 P1 F6 90.45(13) . . ? F5 P1 F2 90.41(13) . . ? F1 P1 F2 178.81(14) . . ? F3 P1 F2 89.37(14) . . ? F6 P1 F2 88.82(12) . . ? F5 P1 F4 89.15(12) . . ? F1 P1 F4 90.61(13) . . ? F3 P1 F4 89.19(12) . . ? F6 P1 F4 179.15(14) . . ? F2 P1 F4 90.40(12) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 0.50 _diffrn_measured_fraction_theta_full 0.000 _refine_diff_density_max 1.519 _refine_diff_density_min -0.614 _refine_diff_density_rms 0.088