Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Martin Broering' 'Serguei Prikhodovski' 'Carsten D. Brandt' _publ_contact_author 'Dr. Martin Br\"oring' _publ_contact_author_address ; Dr. Martin Br\"oring Institut f\"ur Anorganische Chemie Universit\"at W\"urzburg Am Hubland D-97074 W\"urzburg Germany ; _publ_contact_author_phone '049 931 888 5267' _publ_contact_author_fax '049 931 888 4605' _publ_contact_author_email Martin.Broering@mail.uni-wuerzburg.de _publ_requested_journal 'J. Chem. Soc., Dalton Trans.' _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for publication in "J. Chem. Soc., Dalton Trans." ; _publ_section_title ; First (Tripyrrinato)nickel(II) complexes TrpyNiX with X == Cl, Br, I: Synthesis, structures and solvent coordination ; _publ_section_abstract ; A first series of nickel(II)complexes TrpyNi(II)X of the new tripyrrolic ligand 2,15-dimethyl-3,4,8,9,13,14-hexaethyltripyrrin with X == Cl, Br and I was prepared and characterized by spectroscopic and structural means. The coordination geometry found for the four-coordinate, paramagnetic bromo- and iodo-derivatives in the solid state can best be described as distorted trigonal-bipyramidal with one ligand missing in the trigonal plane. For the chloro derivative, this empty site is occupied in the crystal by a water ligand. As proton nmr studies on the paramagnetic TrpyNiCl reveal, an equilibrium exists between the four- and five-, but not a six coordinate form, and for pyridine-N-oxide as the fifth ligand thermodynamic data of the ligand association could be obtained by a temperature dependent nmr titration study. ; data_Cl _database_code_CSD 180751 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H40 Cl N3 Ni O' _chemical_formula_weight 528.79 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' 'Cl' 'Cl' 0.1484 0.1585 '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 P2(1)/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 13.5240(8) _cell_length_b 18.8187(11) _cell_length_c 11.6553(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.2280(10) _cell_angle_gamma 90.00 _cell_volume 2848.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6635 _cell_measurement_theta_min 2.313 _cell_measurement_theta_max 27.417 _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.799 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS2.0 (Sheldrick 2000)' _exptl_special_details ; 'crystals were grown by slow evaporation of acetone at room temperature.' ; _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 'Bruker Smart Apex with D8-goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39984 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5014 _reflns_number_gt 4705 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.6' _computing_cell_refinement 'SAINT-NT V6.0' _computing_data_reduction 'SAINT-NT V6.0' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHELL in SHELXTL-97' _computing_publication_material 'XSHELL in SHELXTL-97' _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^)+(0.0326P)^2^+2.7831P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5014 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.1064 _refine_ls_goodness_of_fit_ref 1.233 _refine_ls_restrained_S_all 1.233 _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 C1 C 0.1484(3) 0.84787(16) -0.0642(3) 0.0354(7) Uani 1 1 d . . . H1A H 0.1139 0.8377 -0.0024 0.053 Uiso 1 1 calc R . . H1B H 0.0985 0.8443 -0.1432 0.053 Uiso 1 1 calc R . . H1C H 0.1771 0.8960 -0.0527 0.053 Uiso 1 1 calc R . . C2 C 0.2326(2) 0.79581(15) -0.0553(2) 0.0255(6) Uani 1 1 d . . . C3 C 0.3251(2) 0.80700(15) -0.0919(2) 0.0264(6) Uani 1 1 d . . . C4 C 0.3773(2) 0.74433(15) -0.0750(2) 0.0254(6) Uani 1 1 d . . . C5 C 0.3174(2) 0.69541(15) -0.0269(2) 0.0231(6) Uani 1 1 d . . . C6 C 0.3423(2) 0.62709(15) 0.0103(2) 0.0234(6) Uani 1 1 d . . . H6 H 0.4055 0.6098 0.0006 0.028 Uiso 1 1 calc R . . C7 C 0.2866(2) 0.57898(14) 0.0611(2) 0.0226(6) Uani 1 1 d . . . C8 C 0.3185(2) 0.50888(15) 0.1030(2) 0.0235(6) Uani 1 1 d . . . C9 C 0.2396(2) 0.48013(15) 0.1404(2) 0.0239(6) Uani 1 1 d . . . C10 C 0.1613(2) 0.53323(15) 0.1209(2) 0.0230(6) Uani 1 1 d . . . C11 C 0.0639(2) 0.52643(16) 0.1446(2) 0.0254(6) Uani 1 1 d . . . H11 H 0.0500 0.4817 0.1745 0.030 Uiso 1 1 calc R . . C12 C -0.0115(2) 0.57599(16) 0.1296(2) 0.0249(6) Uani 1 1 d . . . C13 C -0.1105(2) 0.56793(17) 0.1550(2) 0.0299(7) Uani 1 1 d . . . C14 C -0.1616(2) 0.62986(17) 0.1234(3) 0.0309(7) Uani 1 1 d . . . C15 C -0.0948(2) 0.67570(16) 0.0797(3) 0.0292(7) Uani 1 1 d . . . C16 C -0.1187(2) 0.74928(17) 0.0347(3) 0.0361(7) Uani 1 1 d . . . H16A H -0.1055 0.7823 0.1024 0.054 Uiso 1 1 calc R . . H16B H -0.1913 0.7523 -0.0113 0.054 Uiso 1 1 calc R . . H16C H -0.0752 0.7619 -0.0167 0.054 Uiso 1 1 calc R . . C17 C 0.3570(2) 0.87700(16) -0.1306(3) 0.0348(7) Uani 1 1 d . . . H17A H 0.2960 0.9013 -0.1829 0.042 Uiso 1 1 calc R . . H17B H 0.4068 0.8690 -0.1774 0.042 Uiso 1 1 calc R . . C18 C 0.4059(3) 0.9242(2) -0.0238(4) 0.0638(12) Uani 1 1 d . . . H18A H 0.3564 0.9324 0.0222 0.096 Uiso 1 1 calc R . . H18B H 0.4255 0.9697 -0.0519 0.096 Uiso 1 1 calc R . . H18C H 0.4673 0.9007 0.0271 0.096 Uiso 1 1 calc R . . C19 C 0.4751(2) 0.72755(18) -0.1061(3) 0.0358(7) Uani 1 1 d . . . H19A H 0.5121 0.6894 -0.0528 0.043 Uiso 1 1 calc R . . H19B H 0.5197 0.7702 -0.0919 0.043 Uiso 1 1 calc R . . C20 C 0.4565(3) 0.7041(2) -0.2350(3) 0.0522(10) Uani 1 1 d . . . H20A H 0.4117 0.6622 -0.2499 0.078 Uiso 1 1 calc R . . H20B H 0.5224 0.6924 -0.2499 0.078 Uiso 1 1 calc R . . H20C H 0.4232 0.7427 -0.2884 0.078 Uiso 1 1 calc R . . C21 C 0.4198(2) 0.47526(16) 0.1057(3) 0.0303(7) Uani 1 1 d . . . H21A H 0.4326 0.4821 0.0268 0.036 Uiso 1 1 calc R . . H21B H 0.4151 0.4235 0.1185 0.036 Uiso 1 1 calc R . . C22 C 0.5111(2) 0.50478(19) 0.2020(3) 0.0400(8) Uani 1 1 d . . . H22A H 0.5174 0.5559 0.1894 0.060 Uiso 1 1 calc R . . H22B H 0.5743 0.4807 0.1979 0.060 Uiso 1 1 calc R . . H22C H 0.5005 0.4968 0.2808 0.060 Uiso 1 1 calc R . . C23 C 0.2344(2) 0.40750(15) 0.1924(3) 0.0303(7) Uani 1 1 d . . . H23A H 0.2787 0.3747 0.1623 0.036 Uiso 1 1 calc R . . H23B H 0.1628 0.3897 0.1641 0.036 Uiso 1 1 calc R . . C24 C 0.2680(4) 0.4063(2) 0.3271(3) 0.0622(12) Uani 1 1 d . . . H24A H 0.3392 0.4233 0.3559 0.093 Uiso 1 1 calc R . . H24B H 0.2637 0.3577 0.3552 0.093 Uiso 1 1 calc R . . H24C H 0.2229 0.4373 0.3577 0.093 Uiso 1 1 calc R . . C25 C -0.1432(2) 0.50299(19) 0.2087(3) 0.0393(8) Uani 1 1 d . . . H25A H -0.1223 0.4603 0.1718 0.047 Uiso 1 1 calc R . . H25B H -0.2193 0.5026 0.1904 0.047 Uiso 1 1 calc R . . C26 C -0.0969(4) 0.4994(3) 0.3431(4) 0.0725(14) Uani 1 1 d . . . H26A H -0.0216 0.4994 0.3618 0.109 Uiso 1 1 calc R . . H26B H -0.1198 0.4558 0.3739 0.109 Uiso 1 1 calc R . . H26C H -0.1194 0.5407 0.3805 0.109 Uiso 1 1 calc R . . C27 C -0.2682(2) 0.6491(2) 0.1289(3) 0.0405(8) Uani 1 1 d . . . H27A H -0.3095 0.6052 0.1227 0.049 Uiso 1 1 calc R . . H27B H -0.3013 0.6794 0.0593 0.049 Uiso 1 1 calc R . . C28 C -0.2694(3) 0.6881(2) 0.2425(4) 0.0599(11) Uani 1 1 d . . . H28A H -0.2444 0.6564 0.3112 0.090 Uiso 1 1 calc R . . H28B H -0.3399 0.7031 0.2374 0.090 Uiso 1 1 calc R . . H28C H -0.2248 0.7300 0.2523 0.090 Uiso 1 1 calc R . . Cl1 Cl 0.01622(6) 0.67646(4) -0.17626(6) 0.03475(19) Uani 1 1 d . . . O1 O 0.14732(18) 0.75184(13) 0.1761(2) 0.0352(5) Uani 1 1 d . . . H29A H 0.116(3) 0.766(2) 0.212(4) 0.053 Uiso 1 1 d . . . H29B H 0.206(3) 0.756(2) 0.211(4) 0.053 Uiso 1 1 d . . . N1 N 0.22831(17) 0.72979(12) -0.01688(19) 0.0228(5) Uani 1 1 d . . . N2 N 0.19119(17) 0.59309(12) 0.07395(19) 0.0222(5) Uani 1 1 d . . . N3 N -0.00686(17) 0.64427(13) 0.0834(2) 0.0246(5) Uani 1 1 d . . . Ni1 Ni 0.11101(3) 0.681413(19) 0.02672(3) 0.02219(12) 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 C1 0.0454(19) 0.0255(16) 0.0381(17) 0.0016(13) 0.0165(15) 0.0068(14) C2 0.0303(15) 0.0253(15) 0.0196(13) -0.0008(11) 0.0049(12) -0.0029(12) C3 0.0285(15) 0.0266(15) 0.0229(14) 0.0034(12) 0.0050(12) -0.0064(12) C4 0.0228(14) 0.0303(16) 0.0220(14) 0.0035(12) 0.0046(11) -0.0031(12) C5 0.0217(14) 0.0251(15) 0.0229(14) 0.0007(11) 0.0069(11) -0.0015(11) C6 0.0177(13) 0.0286(15) 0.0250(14) -0.0019(12) 0.0076(11) 0.0018(11) C7 0.0235(14) 0.0232(14) 0.0218(13) -0.0004(11) 0.0076(11) 0.0009(11) C8 0.0239(14) 0.0253(15) 0.0219(14) -0.0019(11) 0.0072(11) 0.0009(12) C9 0.0223(14) 0.0246(15) 0.0239(14) -0.0016(11) 0.0051(11) -0.0030(11) C10 0.0222(14) 0.0246(15) 0.0226(14) -0.0001(11) 0.0068(11) -0.0043(11) C11 0.0270(15) 0.0294(16) 0.0207(14) 0.0019(12) 0.0079(11) -0.0030(12) C12 0.0219(14) 0.0340(16) 0.0204(14) 0.0005(12) 0.0085(11) -0.0023(12) C13 0.0247(15) 0.0439(19) 0.0229(14) -0.0045(13) 0.0094(12) -0.0070(13) C14 0.0235(15) 0.0428(18) 0.0271(15) -0.0102(13) 0.0080(12) -0.0033(13) C15 0.0248(15) 0.0373(18) 0.0242(15) -0.0029(13) 0.0047(12) 0.0012(13) C16 0.0290(17) 0.0420(19) 0.0364(17) 0.0008(14) 0.0078(14) 0.0082(14) C17 0.0370(17) 0.0289(17) 0.0357(17) 0.0085(13) 0.0058(14) -0.0072(14) C18 0.075(3) 0.040(2) 0.060(3) 0.0093(19) -0.007(2) -0.028(2) C19 0.0249(16) 0.0382(18) 0.0464(19) 0.0123(15) 0.0136(14) -0.0014(13) C20 0.052(2) 0.062(3) 0.052(2) 0.0105(19) 0.0313(19) 0.0156(19) C21 0.0297(16) 0.0274(16) 0.0378(17) 0.0035(13) 0.0158(13) 0.0039(13) C22 0.0265(16) 0.050(2) 0.0432(19) 0.0057(16) 0.0093(14) 0.0081(15) C23 0.0257(15) 0.0226(15) 0.0438(18) 0.0055(13) 0.0118(13) 0.0000(12) C24 0.085(3) 0.048(2) 0.046(2) 0.0209(18) 0.004(2) -0.016(2) C25 0.0331(18) 0.047(2) 0.0450(19) 0.0000(16) 0.0224(15) -0.0098(15) C26 0.100(4) 0.075(3) 0.048(2) 0.021(2) 0.031(2) -0.017(3) C27 0.0250(16) 0.055(2) 0.0442(19) -0.0045(16) 0.0146(14) -0.0005(15) C28 0.051(2) 0.075(3) 0.064(3) -0.017(2) 0.033(2) 0.005(2) Cl1 0.0312(4) 0.0462(5) 0.0260(4) 0.0049(3) 0.0064(3) -0.0097(3) O1 0.0319(12) 0.0481(14) 0.0275(12) -0.0090(10) 0.0112(10) 0.0029(11) N1 0.0254(12) 0.0214(12) 0.0228(12) 0.0001(9) 0.0089(10) -0.0009(10) N2 0.0211(11) 0.0234(12) 0.0236(12) 0.0024(9) 0.0085(9) 0.0008(10) N3 0.0204(12) 0.0314(14) 0.0232(12) 0.0027(10) 0.0078(9) 0.0024(10) Ni1 0.0213(2) 0.0242(2) 0.0227(2) 0.00212(14) 0.00879(14) 0.00183(14) _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 C1 C2 1.484(4) . ? C2 N1 1.327(4) . ? C2 C3 1.445(4) . ? C3 C4 1.360(4) . ? C3 C17 1.495(4) . ? C4 C5 1.440(4) . ? C4 C19 1.499(4) . ? C5 C6 1.368(4) . ? C5 N1 1.401(3) . ? C6 C7 1.410(4) . ? C7 N2 1.366(3) . ? C7 C8 1.431(4) . ? C8 C9 1.372(4) . ? C8 C21 1.501(4) . ? C9 C10 1.427(4) . ? C9 C23 1.505(4) . ? C10 N2 1.362(3) . ? C10 C11 1.425(4) . ? C11 C12 1.356(4) . ? C12 N3 1.401(4) . ? C12 C13 1.457(4) . ? C13 C14 1.352(4) . ? C13 C25 1.496(4) . ? C14 C15 1.441(4) . ? C14 C27 1.505(4) . ? C15 N3 1.318(4) . ? C15 C16 1.484(4) . ? C17 C18 1.521(5) . ? C19 C20 1.517(5) . ? C21 C22 1.523(4) . ? C23 C24 1.508(5) . ? C25 C26 1.517(5) . ? C27 C28 1.519(5) . ? Cl1 Ni1 2.3567(8) . ? O1 Ni1 2.133(2) . ? N1 Ni1 2.013(2) . ? N2 Ni1 1.977(2) . ? N3 Ni1 2.014(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 C2 C3 111.0(3) . . ? N1 C2 C1 122.4(3) . . ? C3 C2 C1 126.5(3) . . ? C4 C3 C2 106.8(2) . . ? C4 C3 C17 128.7(3) . . ? C2 C3 C17 124.3(3) . . ? C3 C4 C5 106.5(2) . . ? C3 C4 C19 127.3(3) . . ? C5 C4 C19 126.2(3) . . ? C6 C5 N1 123.3(2) . . ? C6 C5 C4 127.5(3) . . ? N1 C5 C4 109.2(2) . . ? C5 C6 C7 128.6(3) . . ? N2 C7 C6 123.6(2) . . ? N2 C7 C8 110.2(2) . . ? C6 C7 C8 126.2(3) . . ? C9 C8 C7 106.6(2) . . ? C9 C8 C21 127.9(3) . . ? C7 C8 C21 125.6(3) . . ? C8 C9 C10 106.4(2) . . ? C8 C9 C23 127.9(3) . . ? C10 C9 C23 125.7(2) . . ? N2 C10 C11 123.1(3) . . ? N2 C10 C9 110.7(2) . . ? C11 C10 C9 126.3(3) . . ? C12 C11 C10 128.0(3) . . ? C11 C12 N3 124.6(2) . . ? C11 C12 C13 127.0(3) . . ? N3 C12 C13 108.4(2) . . ? C14 C13 C12 106.5(3) . . ? C14 C13 C25 129.0(3) . . ? C12 C13 C25 124.5(3) . . ? C13 C14 C15 106.8(3) . . ? C13 C14 C27 128.3(3) . . ? C15 C14 C27 124.9(3) . . ? N3 C15 C14 111.6(3) . . ? N3 C15 C16 122.4(3) . . ? C14 C15 C16 126.0(3) . . ? C3 C17 C18 111.3(3) . . ? C4 C19 C20 112.8(3) . . ? C8 C21 C22 114.1(3) . . ? C9 C23 C24 113.5(3) . . ? C13 C25 C26 112.5(3) . . ? C14 C27 C28 113.4(3) . . ? C2 N1 C5 106.5(2) . . ? C2 N1 Ni1 128.3(2) . . ? C5 N1 Ni1 124.67(18) . . ? C10 N2 C7 106.2(2) . . ? C10 N2 Ni1 127.31(18) . . ? C7 N2 Ni1 126.46(18) . . ? C15 N3 C12 106.7(2) . . ? C15 N3 Ni1 128.6(2) . . ? C12 N3 Ni1 124.66(18) . . ? N2 Ni1 N1 92.34(9) . . ? N2 Ni1 N3 92.27(9) . . ? N1 Ni1 N3 172.54(9) . . ? N2 Ni1 O1 108.17(9) . . ? N1 Ni1 O1 84.68(9) . . ? N3 Ni1 O1 88.31(9) . . ? N2 Ni1 Cl1 110.39(7) . . ? N1 Ni1 Cl1 90.60(7) . . ? N3 Ni1 Cl1 93.29(7) . . ? O1 Ni1 Cl1 141.30(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 0.5(3) . . . . ? C1 C2 C3 C4 -176.2(3) . . . . ? N1 C2 C3 C17 -175.1(3) . . . . ? C1 C2 C3 C17 8.2(5) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C17 C3 C4 C5 174.6(3) . . . . ? C2 C3 C4 C19 176.3(3) . . . . ? C17 C3 C4 C19 -8.4(5) . . . . ? C3 C4 C5 C6 -176.1(3) . . . . ? C19 C4 C5 C6 6.8(5) . . . . ? C3 C4 C5 N1 0.7(3) . . . . ? C19 C4 C5 N1 -176.3(3) . . . . ? N1 C5 C6 C7 1.4(5) . . . . ? C4 C5 C6 C7 177.8(3) . . . . ? C5 C6 C7 N2 4.7(5) . . . . ? C5 C6 C7 C8 -177.2(3) . . . . ? N2 C7 C8 C9 0.8(3) . . . . ? C6 C7 C8 C9 -177.5(3) . . . . ? N2 C7 C8 C21 -178.5(2) . . . . ? C6 C7 C8 C21 3.1(4) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C21 C8 C9 C10 179.1(3) . . . . ? C7 C8 C9 C23 -179.9(3) . . . . ? C21 C8 C9 C23 -0.6(5) . . . . ? C8 C9 C10 N2 -0.5(3) . . . . ? C23 C9 C10 N2 179.3(3) . . . . ? C8 C9 C10 C11 178.7(3) . . . . ? C23 C9 C10 C11 -1.6(4) . . . . ? N2 C10 C11 C12 -2.4(5) . . . . ? C9 C10 C11 C12 178.6(3) . . . . ? C10 C11 C12 N3 1.9(5) . . . . ? C10 C11 C12 C13 -179.7(3) . . . . ? C11 C12 C13 C14 -178.3(3) . . . . ? N3 C12 C13 C14 0.4(3) . . . . ? C11 C12 C13 C25 3.2(5) . . . . ? N3 C12 C13 C25 -178.1(3) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C25 C13 C14 C15 178.1(3) . . . . ? C12 C13 C14 C27 178.6(3) . . . . ? C25 C13 C14 C27 -3.0(5) . . . . ? C13 C14 C15 N3 0.1(3) . . . . ? C27 C14 C15 N3 -178.8(3) . . . . ? C13 C14 C15 C16 179.8(3) . . . . ? C27 C14 C15 C16 0.9(5) . . . . ? C4 C3 C17 C18 -95.6(4) . . . . ? C2 C3 C17 C18 79.0(4) . . . . ? C3 C4 C19 C20 -85.2(4) . . . . ? C5 C4 C19 C20 91.2(4) . . . . ? C9 C8 C21 C22 -106.3(3) . . . . ? C7 C8 C21 C22 73.0(4) . . . . ? C8 C9 C23 C24 94.5(4) . . . . ? C10 C9 C23 C24 -85.1(4) . . . . ? C14 C13 C25 C26 -98.8(4) . . . . ? C12 C13 C25 C26 79.3(4) . . . . ? C13 C14 C27 C28 95.0(4) . . . . ? C15 C14 C27 C28 -86.4(4) . . . . ? C3 C2 N1 C5 -0.1(3) . . . . ? C1 C2 N1 C5 176.8(3) . . . . ? C3 C2 N1 Ni1 -172.31(18) . . . . ? C1 C2 N1 Ni1 4.5(4) . . . . ? C6 C5 N1 C2 176.6(3) . . . . ? C4 C5 N1 C2 -0.4(3) . . . . ? C6 C5 N1 Ni1 -10.8(4) . . . . ? C4 C5 N1 Ni1 172.21(17) . . . . ? C11 C10 N2 C7 -178.3(2) . . . . ? C9 C10 N2 C7 0.9(3) . . . . ? C11 C10 N2 Ni1 -0.7(4) . . . . ? C9 C10 N2 Ni1 178.46(18) . . . . ? C6 C7 N2 C10 177.3(3) . . . . ? C8 C7 N2 C10 -1.1(3) . . . . ? C6 C7 N2 Ni1 -0.2(4) . . . . ? C8 C7 N2 Ni1 -178.61(18) . . . . ? C14 C15 N3 C12 0.1(3) . . . . ? C16 C15 N3 C12 -179.6(3) . . . . ? C14 C15 N3 Ni1 176.85(18) . . . . ? C16 C15 N3 Ni1 -2.9(4) . . . . ? C11 C12 N3 C15 178.4(3) . . . . ? C13 C12 N3 C15 -0.3(3) . . . . ? C11 C12 N3 Ni1 1.5(4) . . . . ? C13 C12 N3 Ni1 -177.19(17) . . . . ? C10 N2 Ni1 N1 176.9(2) . . . . ? C7 N2 Ni1 N1 -6.0(2) . . . . ? C10 N2 Ni1 N3 2.8(2) . . . . ? C7 N2 Ni1 N3 179.8(2) . . . . ? C10 N2 Ni1 O1 91.8(2) . . . . ? C7 N2 Ni1 O1 -91.2(2) . . . . ? C10 N2 Ni1 Cl1 -91.6(2) . . . . ? C7 N2 Ni1 Cl1 85.5(2) . . . . ? C2 N1 Ni1 N2 -177.8(2) . . . . ? C5 N1 Ni1 N2 11.3(2) . . . . ? C2 N1 Ni1 N3 -49.6(8) . . . . ? C5 N1 Ni1 N3 139.4(6) . . . . ? C2 N1 Ni1 O1 -69.8(2) . . . . ? C5 N1 Ni1 O1 119.3(2) . . . . ? C2 N1 Ni1 Cl1 71.8(2) . . . . ? C5 N1 Ni1 Cl1 -99.2(2) . . . . ? C15 N3 Ni1 N2 -179.3(2) . . . . ? C12 N3 Ni1 N2 -3.1(2) . . . . ? C15 N3 Ni1 N1 52.5(8) . . . . ? C12 N3 Ni1 N1 -131.3(7) . . . . ? C15 N3 Ni1 O1 72.6(2) . . . . ? C12 N3 Ni1 O1 -111.2(2) . . . . ? C15 N3 Ni1 Cl1 -68.7(2) . . . . ? C12 N3 Ni1 Cl1 107.5(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.411 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.061 #======END data_serguei3 _database_code_CSD 180752 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H38 Br N3 Ni' _chemical_formula_weight 555.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.4039(6) _cell_length_b 20.7216(11) _cell_length_c 11.5191(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.4160(10) _cell_angle_gamma 90.00 _cell_volume 2719.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7605 _cell_measurement_theta_min 2.462 _cell_measurement_theta_max 28.298 _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 2.202 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS2.0 (Sheldrick 2000)' _exptl_special_details ; ? ; _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 'Bruker Smart Apex with D8-goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32189 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4773 _reflns_number_gt 4432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.6' _computing_cell_refinement 'SAINT-NT V6.0' _computing_data_reduction 'SAINT-NT V6.0' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHELL in SHELXTL-97' _computing_publication_material 'XSHELL in SHELXTL-97' _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^)+(0.0434P)^2^+0.9656P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4773 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0711 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.003 _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 Br1 Br 1.222812(18) 0.096489(10) 0.724404(17) 0.03371(8) Uani 1 1 d . . . C1 C 1.25829(18) 0.06294(10) 1.05361(18) 0.0344(5) Uani 1 1 d . . . H1A H 1.2553 0.0198 1.0188 0.052 Uiso 1 1 calc R . . H1B H 1.2820 0.0594 1.1362 0.052 Uiso 1 1 calc R . . H1C H 1.3153 0.0895 1.0139 0.052 Uiso 1 1 calc R . . C2 C 1.13989(18) 0.09354(9) 1.04148(17) 0.0272(4) Uani 1 1 d . . . C3 C 1.09368(18) 0.14300(9) 1.11494(16) 0.0282(4) Uani 1 1 d . . . C4 C 0.98368(17) 0.15647(9) 1.07181(16) 0.0278(4) Uani 1 1 d . . . C5 C 0.96263(17) 0.11539(9) 0.97061(16) 0.0269(4) Uani 1 1 d . . . C6 C 0.86460(17) 0.11312(9) 0.89903(16) 0.0271(4) Uani 1 1 d . . . H6 H 0.8030 0.1417 0.9175 0.033 Uiso 1 1 calc R . . C7 C 0.84310(16) 0.07318(9) 0.79993(17) 0.0260(4) Uani 1 1 d . . . C8 C 0.73824(17) 0.06882(10) 0.72889(16) 0.0272(4) Uani 1 1 d . . . C9 C 0.75906(17) 0.02305(9) 0.64372(17) 0.0262(4) Uani 1 1 d . . . C10 C 0.87627(16) 0.00095(9) 0.66639(16) 0.0243(4) Uani 1 1 d . . . C11 C 0.93681(16) -0.04668(9) 0.60242(16) 0.0250(4) Uani 1 1 d . . . H11 H 0.8968 -0.0628 0.5345 0.030 Uiso 1 1 calc R . . C12 C 1.04565(16) -0.07167(9) 0.62771(16) 0.0241(4) Uani 1 1 d . . . C13 C 1.10650(17) -0.12077(9) 0.56235(16) 0.0260(4) Uani 1 1 d . . . C14 C 1.21396(17) -0.12877(9) 0.61671(16) 0.0263(4) Uani 1 1 d . . . C15 C 1.21858(16) -0.08521(9) 0.71523(16) 0.0261(4) Uani 1 1 d . . . C16 C 1.32054(19) -0.07547(11) 0.79829(19) 0.0359(5) Uani 1 1 d . . . H16A H 1.3696 -0.0403 0.7707 0.054 Uiso 1 1 calc R . . H16B H 1.3669 -0.1152 0.8039 0.054 Uiso 1 1 calc R . . H16C H 1.2923 -0.0644 0.8750 0.054 Uiso 1 1 calc R . . C17 C 1.1585(2) 0.17187(10) 1.21928(17) 0.0352(5) Uani 1 1 d . . . H17A H 1.1860 0.1364 1.2711 0.042 Uiso 1 1 calc R . . H17B H 1.1028 0.1983 1.2626 0.042 Uiso 1 1 calc R . . C18 C 1.2627(2) 0.21340(13) 1.1914(2) 0.0528(7) Uani 1 1 d . . . H18A H 1.3198 0.1874 1.1505 0.079 Uiso 1 1 calc R . . H18B H 1.2995 0.2301 1.2637 0.079 Uiso 1 1 calc R . . H18C H 1.2364 0.2495 1.1420 0.079 Uiso 1 1 calc R . . C19 C 0.89784(19) 0.20499(10) 1.11568(18) 0.0339(5) Uani 1 1 d . . . H19A H 0.9105 0.2094 1.2009 0.041 Uiso 1 1 calc R . . H19B H 0.8171 0.1887 1.1002 0.041 Uiso 1 1 calc R . . C20 C 0.9088(2) 0.27094(11) 1.0600(2) 0.0510(6) Uani 1 1 d . . . H20A H 0.9876 0.2882 1.0776 0.077 Uiso 1 1 calc R . . H20B H 0.8502 0.3002 1.0909 0.077 Uiso 1 1 calc R . . H20C H 0.8958 0.2671 0.9757 0.077 Uiso 1 1 calc R . . C21 C 0.62611(18) 0.10578(10) 0.74640(19) 0.0350(5) Uani 1 1 d . . . H21A H 0.5777 0.1049 0.6731 0.042 Uiso 1 1 calc R . . H21B H 0.6461 0.1514 0.7635 0.042 Uiso 1 1 calc R . . C22 C 0.5537(2) 0.07956(14) 0.8437(2) 0.0538(7) Uani 1 1 d . . . H22A H 0.5360 0.0339 0.8292 0.081 Uiso 1 1 calc R . . H22B H 0.4802 0.1039 0.8467 0.081 Uiso 1 1 calc R . . H22C H 0.5981 0.0839 0.9180 0.081 Uiso 1 1 calc R . . C23 C 0.67722(18) -0.00088(10) 0.54790(18) 0.0321(4) Uani 1 1 d . . . H23A H 0.7217 -0.0063 0.4766 0.039 Uiso 1 1 calc R . . H23B H 0.6159 0.0321 0.5317 0.039 Uiso 1 1 calc R . . C24 C 0.6185(2) -0.06435(12) 0.5760(2) 0.0486(6) Uani 1 1 d . . . H24A H 0.6787 -0.0972 0.5927 0.073 Uiso 1 1 calc R . . H24B H 0.5684 -0.0781 0.5093 0.073 Uiso 1 1 calc R . . H24C H 0.5707 -0.0588 0.6439 0.073 Uiso 1 1 calc R . . C25 C 1.05666(18) -0.15456(9) 0.45638(17) 0.0311(4) Uani 1 1 d . . . H25A H 1.1222 -0.1692 0.4093 0.037 Uiso 1 1 calc R . . H25B H 1.0096 -0.1233 0.4090 0.037 Uiso 1 1 calc R . . C26 C 0.9798(2) -0.21236(12) 0.4825(2) 0.0491(6) Uani 1 1 d . . . H26A H 1.0244 -0.2428 0.5324 0.074 Uiso 1 1 calc R . . H26B H 0.9553 -0.2338 0.4097 0.074 Uiso 1 1 calc R . . H26C H 0.9104 -0.1978 0.5224 0.074 Uiso 1 1 calc R . . C27 C 1.31317(18) -0.17200(10) 0.58359(18) 0.0319(4) Uani 1 1 d . . . H27A H 1.3885 -0.1505 0.6052 0.038 Uiso 1 1 calc R . . H27B H 1.3095 -0.1777 0.4982 0.038 Uiso 1 1 calc R . . C28 C 1.3117(2) -0.23826(11) 0.6407(2) 0.0491(6) Uani 1 1 d . . . H28A H 1.3198 -0.2333 0.7252 0.074 Uiso 1 1 calc R . . H28B H 1.3771 -0.2641 0.6136 0.074 Uiso 1 1 calc R . . H28C H 1.2374 -0.2599 0.6200 0.074 Uiso 1 1 calc R . . N1 N 1.06323(14) 0.07705(8) 0.95703(14) 0.0262(3) Uani 1 1 d . . . N2 N 0.92575(13) 0.03150(7) 0.76099(14) 0.0246(3) Uani 1 1 d . . . N3 N 1.11979(13) -0.05206(7) 0.72199(13) 0.0247(3) Uani 1 1 d . . . Ni1 Ni 1.08885(2) 0.025226(11) 0.81649(2) 0.02390(8) 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 Br1 0.03469(13) 0.03005(13) 0.03665(13) -0.00011(8) 0.00444(9) -0.00721(8) C1 0.0349(11) 0.0346(11) 0.0332(11) -0.0007(9) -0.0039(9) 0.0023(9) C2 0.0321(11) 0.0246(10) 0.0250(10) 0.0034(7) 0.0035(8) -0.0026(8) C3 0.0365(11) 0.0264(10) 0.0219(9) 0.0013(8) 0.0044(8) -0.0055(8) C4 0.0333(11) 0.0238(10) 0.0268(10) -0.0001(8) 0.0088(8) -0.0040(8) C5 0.0285(10) 0.0241(9) 0.0286(10) 0.0010(8) 0.0070(8) -0.0004(8) C6 0.0273(10) 0.0245(9) 0.0300(10) -0.0009(8) 0.0069(8) 0.0003(8) C7 0.0237(10) 0.0244(10) 0.0301(10) 0.0022(8) 0.0034(8) 0.0007(8) C8 0.0259(10) 0.0256(10) 0.0303(10) 0.0036(8) 0.0025(8) 0.0018(8) C9 0.0255(10) 0.0231(9) 0.0299(10) 0.0040(8) 0.0000(8) -0.0004(8) C10 0.0229(9) 0.0226(9) 0.0274(10) 0.0023(7) 0.0011(8) -0.0005(7) C11 0.0271(10) 0.0222(9) 0.0257(10) 0.0001(7) 0.0004(8) -0.0040(8) C12 0.0277(10) 0.0207(9) 0.0241(9) 0.0004(7) 0.0028(7) -0.0027(8) C13 0.0313(11) 0.0212(9) 0.0260(10) 0.0020(8) 0.0055(8) -0.0001(8) C14 0.0303(10) 0.0202(9) 0.0289(10) 0.0018(7) 0.0062(8) 0.0005(8) C15 0.0254(10) 0.0229(10) 0.0302(10) 0.0017(7) 0.0036(8) -0.0018(7) C16 0.0303(11) 0.0350(12) 0.0420(12) -0.0063(9) -0.0037(9) 0.0051(9) C17 0.0453(12) 0.0362(11) 0.0239(10) -0.0025(8) -0.0009(9) -0.0031(10) C18 0.0667(17) 0.0508(15) 0.0402(13) 0.0008(11) -0.0066(12) -0.0239(13) C19 0.0373(12) 0.0325(11) 0.0326(11) -0.0062(9) 0.0101(9) -0.0015(9) C20 0.0550(15) 0.0317(12) 0.0679(17) 0.0007(11) 0.0218(13) 0.0091(11) C21 0.0289(11) 0.0356(11) 0.0403(12) -0.0029(9) -0.0026(9) 0.0082(9) C22 0.0280(12) 0.0728(18) 0.0614(16) 0.0040(14) 0.0098(11) 0.0108(12) C23 0.0296(11) 0.0325(11) 0.0335(11) -0.0017(9) -0.0074(9) 0.0053(8) C24 0.0407(13) 0.0477(14) 0.0560(15) 0.0016(12) -0.0143(11) -0.0121(11) C25 0.0377(11) 0.0289(10) 0.0269(10) -0.0035(8) 0.0028(8) 0.0039(9) C26 0.0647(17) 0.0426(14) 0.0399(13) -0.0097(11) 0.0007(11) -0.0176(12) C27 0.0306(11) 0.0317(11) 0.0338(11) -0.0033(9) 0.0068(8) 0.0033(8) C28 0.0574(16) 0.0379(13) 0.0533(15) 0.0075(11) 0.0170(12) 0.0223(11) N1 0.0293(9) 0.0243(8) 0.0251(8) -0.0013(6) 0.0012(7) 0.0010(7) N2 0.0224(8) 0.0240(8) 0.0274(8) -0.0020(6) 0.0016(6) -0.0009(6) N3 0.0247(8) 0.0216(8) 0.0278(8) -0.0012(6) 0.0020(6) -0.0003(6) Ni1 0.02172(14) 0.02285(14) 0.02710(14) -0.00365(9) 0.00078(10) 0.00031(9) _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 Br1 Ni1 2.4034(3) . ? C1 C2 1.493(3) . ? C2 N1 1.325(3) . ? C2 C3 1.443(3) . ? C3 C4 1.359(3) . ? C3 C17 1.508(3) . ? C4 C5 1.455(3) . ? C4 C19 1.505(3) . ? C5 C6 1.362(3) . ? C5 N1 1.410(2) . ? C6 C7 1.423(3) . ? C7 N2 1.368(2) . ? C7 C8 1.423(3) . ? C8 C9 1.392(3) . ? C8 C21 1.511(3) . ? C9 C10 1.427(3) . ? C9 C23 1.499(3) . ? C10 N2 1.362(2) . ? C10 C11 1.427(3) . ? C11 C12 1.365(3) . ? C12 N3 1.408(2) . ? C12 C13 1.459(3) . ? C13 C14 1.363(3) . ? C13 C25 1.498(3) . ? C14 C15 1.449(3) . ? C14 C27 1.505(3) . ? C15 N3 1.325(2) . ? C15 C16 1.488(3) . ? C17 C18 1.513(3) . ? C19 C20 1.517(3) . ? C21 C22 1.521(3) . ? C23 C24 1.516(3) . ? C25 C26 1.521(3) . ? C27 C28 1.523(3) . ? N1 Ni1 1.9746(16) . ? N2 Ni1 1.9456(16) . ? N3 Ni1 1.9765(15) . ? 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 C2 C3 111.58(18) . . ? N1 C2 C1 121.69(17) . . ? C3 C2 C1 126.73(18) . . ? C4 C3 C2 106.61(17) . . ? C4 C3 C17 128.60(18) . . ? C2 C3 C17 124.78(19) . . ? C3 C4 C5 106.94(17) . . ? C3 C4 C19 128.17(18) . . ? C5 C4 C19 124.88(18) . . ? C6 C5 N1 124.37(17) . . ? C6 C5 C4 127.50(18) . . ? N1 C5 C4 108.12(17) . . ? C5 C6 C7 127.97(18) . . ? N2 C7 C6 122.18(17) . . ? N2 C7 C8 110.19(17) . . ? C6 C7 C8 127.62(17) . . ? C9 C8 C7 106.53(16) . . ? C9 C8 C21 127.57(19) . . ? C7 C8 C21 125.89(18) . . ? C8 C9 C10 106.02(17) . . ? C8 C9 C23 128.67(18) . . ? C10 C9 C23 125.30(17) . . ? N2 C10 C9 110.52(16) . . ? N2 C10 C11 122.79(17) . . ? C9 C10 C11 126.69(18) . . ? C12 C11 C10 127.41(18) . . ? C11 C12 N3 124.49(17) . . ? C11 C12 C13 127.05(17) . . ? N3 C12 C13 108.44(16) . . ? C14 C13 C12 106.61(16) . . ? C14 C13 C25 128.35(17) . . ? C12 C13 C25 125.04(17) . . ? C13 C14 C15 106.64(16) . . ? C13 C14 C27 128.84(18) . . ? C15 C14 C27 124.50(18) . . ? N3 C15 C14 111.47(17) . . ? N3 C15 C16 122.36(17) . . ? C14 C15 C16 126.13(17) . . ? C3 C17 C18 114.80(17) . . ? C4 C19 C20 113.17(17) . . ? C8 C21 C22 113.97(18) . . ? C9 C23 C24 113.36(18) . . ? C13 C25 C26 114.10(17) . . ? C14 C27 C28 113.92(17) . . ? C2 N1 C5 106.74(16) . . ? C2 N1 Ni1 128.78(13) . . ? C5 N1 Ni1 123.15(13) . . ? C10 N2 C7 106.74(16) . . ? C10 N2 Ni1 126.15(12) . . ? C7 N2 Ni1 126.64(13) . . ? C15 N3 C12 106.83(15) . . ? C15 N3 Ni1 128.65(13) . . ? C12 N3 Ni1 122.92(12) . . ? N2 Ni1 N1 93.47(7) . . ? N2 Ni1 N3 93.64(6) . . ? N1 Ni1 N3 158.15(7) . . ? N2 Ni1 Br1 115.50(5) . . ? N1 Ni1 Br1 98.42(5) . . ? N3 Ni1 Br1 97.08(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 0.1(2) . . . . ? C1 C2 C3 C4 179.79(18) . . . . ? N1 C2 C3 C17 179.46(17) . . . . ? C1 C2 C3 C17 -0.9(3) . . . . ? C2 C3 C4 C5 -0.5(2) . . . . ? C17 C3 C4 C5 -179.81(18) . . . . ? C2 C3 C4 C19 -179.34(18) . . . . ? C17 C3 C4 C19 1.3(3) . . . . ? C3 C4 C5 C6 -178.99(19) . . . . ? C19 C4 C5 C6 -0.1(3) . . . . ? C3 C4 C5 N1 0.7(2) . . . . ? C19 C4 C5 N1 179.61(17) . . . . ? N1 C5 C6 C7 0.3(3) . . . . ? C4 C5 C6 C7 180.00(18) . . . . ? C5 C6 C7 N2 -2.4(3) . . . . ? C5 C6 C7 C8 176.63(19) . . . . ? N2 C7 C8 C9 -0.4(2) . . . . ? C6 C7 C8 C9 -179.49(18) . . . . ? N2 C7 C8 C21 178.06(18) . . . . ? C6 C7 C8 C21 -1.1(3) . . . . ? C7 C8 C9 C10 0.2(2) . . . . ? C21 C8 C9 C10 -178.17(18) . . . . ? C7 C8 C9 C23 178.87(19) . . . . ? C21 C8 C9 C23 0.5(3) . . . . ? C8 C9 C10 N2 0.0(2) . . . . ? C23 C9 C10 N2 -178.71(17) . . . . ? C8 C9 C10 C11 179.47(18) . . . . ? C23 C9 C10 C11 0.8(3) . . . . ? N2 C10 C11 C12 4.5(3) . . . . ? C9 C10 C11 C12 -174.92(18) . . . . ? C10 C11 C12 N3 -2.5(3) . . . . ? C10 C11 C12 C13 179.43(18) . . . . ? C11 C12 C13 C14 177.60(18) . . . . ? N3 C12 C13 C14 -0.8(2) . . . . ? C11 C12 C13 C25 -2.4(3) . . . . ? N3 C12 C13 C25 179.20(17) . . . . ? C12 C13 C14 C15 0.4(2) . . . . ? C25 C13 C14 C15 -179.54(18) . . . . ? C12 C13 C14 C27 -178.01(18) . . . . ? C25 C13 C14 C27 2.0(3) . . . . ? C13 C14 C15 N3 0.1(2) . . . . ? C27 C14 C15 N3 178.58(17) . . . . ? C13 C14 C15 C16 -177.91(19) . . . . ? C27 C14 C15 C16 0.6(3) . . . . ? C4 C3 C17 C18 -112.0(3) . . . . ? C2 C3 C17 C18 68.8(3) . . . . ? C3 C4 C19 C20 90.4(3) . . . . ? C5 C4 C19 C20 -88.3(3) . . . . ? C9 C8 C21 C22 101.3(3) . . . . ? C7 C8 C21 C22 -76.7(3) . . . . ? C8 C9 C23 C24 -98.3(2) . . . . ? C10 C9 C23 C24 80.2(3) . . . . ? C14 C13 C25 C26 95.9(2) . . . . ? C12 C13 C25 C26 -84.0(2) . . . . ? C13 C14 C27 C28 -92.3(3) . . . . ? C15 C14 C27 C28 89.6(2) . . . . ? C3 C2 N1 C5 0.3(2) . . . . ? C1 C2 N1 C5 -179.36(17) . . . . ? C3 C2 N1 Ni1 167.26(13) . . . . ? C1 C2 N1 Ni1 -12.4(3) . . . . ? C6 C5 N1 C2 179.07(18) . . . . ? C4 C5 N1 C2 -0.6(2) . . . . ? C6 C5 N1 Ni1 11.2(3) . . . . ? C4 C5 N1 Ni1 -168.47(12) . . . . ? C9 C10 N2 C7 -0.2(2) . . . . ? C11 C10 N2 C7 -179.71(17) . . . . ? C9 C10 N2 Ni1 -172.78(12) . . . . ? C11 C10 N2 Ni1 7.7(3) . . . . ? C6 C7 N2 C10 179.55(17) . . . . ? C8 C7 N2 C10 0.4(2) . . . . ? C6 C7 N2 Ni1 -7.9(3) . . . . ? C8 C7 N2 Ni1 172.87(12) . . . . ? C14 C15 N3 C12 -0.5(2) . . . . ? C16 C15 N3 C12 177.52(17) . . . . ? C14 C15 N3 Ni1 -166.22(12) . . . . ? C16 C15 N3 Ni1 11.9(3) . . . . ? C11 C12 N3 C15 -177.61(17) . . . . ? C13 C12 N3 C15 0.8(2) . . . . ? C11 C12 N3 Ni1 -10.9(2) . . . . ? C13 C12 N3 Ni1 167.48(12) . . . . ? C10 N2 Ni1 N1 -174.62(15) . . . . ? C7 N2 Ni1 N1 14.27(16) . . . . ? C10 N2 Ni1 N3 -15.29(16) . . . . ? C7 N2 Ni1 N3 173.60(15) . . . . ? C10 N2 Ni1 Br1 84.33(15) . . . . ? C7 N2 Ni1 Br1 -86.78(15) . . . . ? C2 N1 Ni1 N2 179.58(16) . . . . ? C5 N1 Ni1 N2 -15.43(15) . . . . ? C2 N1 Ni1 N3 70.8(3) . . . . ? C5 N1 Ni1 N3 -124.25(18) . . . . ? C2 N1 Ni1 Br1 -64.00(16) . . . . ? C5 N1 Ni1 Br1 101.00(14) . . . . ? C15 N3 Ni1 N2 -179.94(16) . . . . ? C12 N3 Ni1 N2 16.45(14) . . . . ? C15 N3 Ni1 N1 -71.2(2) . . . . ? C12 N3 Ni1 N1 125.23(19) . . . . ? C15 N3 Ni1 Br1 63.78(16) . . . . ? C12 N3 Ni1 Br1 -99.82(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.407 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.061 #======END data_sp1cb _database_code_CSD 180753 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H38 I N3 Ni' _chemical_formula_weight 602.22 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' '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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4639(2) _cell_length_b 11.5821(2) _cell_length_c 12.4548(2) _cell_angle_alpha 110.2630(10) _cell_angle_beta 95.8150(10) _cell_angle_gamma 102.2130(10) _cell_volume 1358.66(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7561 _cell_measurement_theta_min 2.780 _cell_measurement_theta_max 30.486 _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 1.870 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS2.0 (Sheldrick 2000)' _exptl_special_details ; ? ; _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 'Bruker Smart Apex with D8-goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22548 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4792 _reflns_number_gt 4687 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.6' _computing_cell_refinement 'SAINT-NT V6.0' _computing_data_reduction 'SAINT-NT V6.0' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHELL in SHELXTL-97' _computing_publication_material 'XSHELL in SHELXTL-97' _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^)+(0.0288P)^2^+1.0970P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4792 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0238 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0583 _refine_ls_wR_factor_gt 0.0579 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1443(2) 0.8847(2) -0.1324(2) 0.0322(5) Uani 1 1 d . . . H1A H 0.0657 0.9175 -0.1205 0.048 Uiso 1 1 calc R . . H1B H 0.1742 0.8938 -0.2018 0.048 Uiso 1 1 calc R . . H1C H 0.2158 0.9332 -0.0641 0.048 Uiso 1 1 calc R . . C2 C 0.1098(2) 0.7474(2) -0.14850(18) 0.0247(4) Uani 1 1 d . . . C3 C 0.0219(2) 0.6430(2) -0.24633(18) 0.0253(4) Uani 1 1 d . . . C4 C 0.0149(2) 0.5358(2) -0.22193(18) 0.0246(4) Uani 1 1 d . . . C5 C 0.10227(19) 0.57446(19) -0.11108(17) 0.0213(4) Uani 1 1 d . . . C6 C 0.1337(2) 0.49712(19) -0.05684(17) 0.0219(4) Uani 1 1 d . . . H6 H 0.0845 0.4100 -0.0907 0.026 Uiso 1 1 calc R . . C7 C 0.2317(2) 0.53230(18) 0.04439(17) 0.0213(4) Uani 1 1 d . . . C8 C 0.2800(2) 0.44843(19) 0.08978(17) 0.0222(4) Uani 1 1 d . . . C9 C 0.3821(2) 0.52505(19) 0.18294(17) 0.0217(4) Uani 1 1 d . . . C10 C 0.3927(2) 0.65368(19) 0.19345(17) 0.0214(4) Uani 1 1 d . . . C11 C 0.4836(2) 0.76561(19) 0.27533(17) 0.0228(4) Uani 1 1 d . . . H11 H 0.5354 0.7557 0.3371 0.027 Uiso 1 1 calc R . . C12 C 0.5060(2) 0.88696(19) 0.27635(17) 0.0226(4) Uani 1 1 d . . . C13 C 0.6027(2) 0.99985(19) 0.35928(18) 0.0248(4) Uani 1 1 d . . . C14 C 0.5961(2) 1.0968(2) 0.32143(19) 0.0262(4) Uani 1 1 d . . . C15 C 0.4948(2) 1.04299(19) 0.21774(19) 0.0258(4) Uani 1 1 d . . . C16 C 0.4502(3) 1.1121(2) 0.1462(2) 0.0369(5) Uani 1 1 d . . . H16A H 0.4154 1.0521 0.0655 0.055 Uiso 1 1 calc R . . H16B H 0.5258 1.1797 0.1482 0.055 Uiso 1 1 calc R . . H16C H 0.3800 1.1498 0.1779 0.055 Uiso 1 1 calc R . . C17 C -0.0444(2) 0.6542(2) -0.35381(19) 0.0302(5) Uani 1 1 d . . . H17A H -0.0576 0.5727 -0.4207 0.036 Uiso 1 1 calc R . . H17B H 0.0159 0.7217 -0.3702 0.036 Uiso 1 1 calc R . . C18 C -0.1776(2) 0.6850(3) -0.3447(2) 0.0392(6) Uani 1 1 d . . . H18A H -0.2383 0.6186 -0.3286 0.059 Uiso 1 1 calc R . . H18B H -0.2157 0.6886 -0.4183 0.059 Uiso 1 1 calc R . . H18C H -0.1650 0.7677 -0.2813 0.059 Uiso 1 1 calc R . . C19 C -0.0610(2) 0.4011(2) -0.29643(19) 0.0297(5) Uani 1 1 d . . . H19A H -0.1318 0.4022 -0.3550 0.036 Uiso 1 1 calc R . . H19B H -0.1047 0.3604 -0.2469 0.036 Uiso 1 1 calc R . . C20 C 0.0276(3) 0.3216(2) -0.3593(2) 0.0353(5) Uani 1 1 d . . . H20A H 0.0758 0.3645 -0.4043 0.053 Uiso 1 1 calc R . . H20B H -0.0276 0.2372 -0.4120 0.053 Uiso 1 1 calc R . . H20C H 0.0916 0.3121 -0.3018 0.053 Uiso 1 1 calc R . . C21 C 0.2326(2) 0.30532(19) 0.03823(18) 0.0259(4) Uani 1 1 d . . . H21A H 0.1347 0.2796 0.0119 0.031 Uiso 1 1 calc R . . H21B H 0.2526 0.2719 0.0994 0.031 Uiso 1 1 calc R . . C22 C 0.2967(3) 0.2455(2) -0.0642(2) 0.0382(6) Uani 1 1 d . . . H22A H 0.2741 0.2752 -0.1265 0.057 Uiso 1 1 calc R . . H22B H 0.2637 0.1523 -0.0932 0.057 Uiso 1 1 calc R . . H22C H 0.3936 0.2703 -0.0387 0.057 Uiso 1 1 calc R . . C23 C 0.4749(2) 0.4838(2) 0.25366(18) 0.0251(4) Uani 1 1 d . . . H23A H 0.4302 0.3982 0.2508 0.030 Uiso 1 1 calc R . . H23B H 0.4945 0.5439 0.3360 0.030 Uiso 1 1 calc R . . C24 C 0.6050(2) 0.4791(3) 0.2101(2) 0.0394(6) Uani 1 1 d . . . H24A H 0.5861 0.4207 0.1283 0.059 Uiso 1 1 calc R . . H24B H 0.6605 0.4489 0.2570 0.059 Uiso 1 1 calc R . . H24C H 0.6522 0.5647 0.2170 0.059 Uiso 1 1 calc R . . C25 C 0.6929(2) 1.0046(2) 0.46239(19) 0.0306(5) Uani 1 1 d . . . H25A H 0.6427 0.9513 0.4995 0.037 Uiso 1 1 calc R . . H25B H 0.7226 1.0935 0.5201 0.037 Uiso 1 1 calc R . . C26 C 0.8147(3) 0.9580(3) 0.4309(2) 0.0498(7) Uani 1 1 d . . . H26A H 0.7862 0.8687 0.3767 0.075 Uiso 1 1 calc R . . H26B H 0.8715 0.9652 0.5017 0.075 Uiso 1 1 calc R . . H26C H 0.8649 1.0102 0.3939 0.075 Uiso 1 1 calc R . . C27 C 0.6746(2) 1.2347(2) 0.3763(2) 0.0315(5) Uani 1 1 d . . . H27A H 0.6962 1.2660 0.3140 0.038 Uiso 1 1 calc R . . H27B H 0.7596 1.2412 0.4238 0.038 Uiso 1 1 calc R . . C28 C 0.6005(3) 1.3190(2) 0.4528(2) 0.0425(6) Uani 1 1 d . . . H28A H 0.5137 1.3088 0.4076 0.064 Uiso 1 1 calc R . . H28B H 0.6524 1.4083 0.4807 0.064 Uiso 1 1 calc R . . H28C H 0.5875 1.2945 0.5195 0.064 Uiso 1 1 calc R . . I I 0.109742(15) 0.912075(14) 0.201000(13) 0.03435(6) Uani 1 1 d . . . N1 N 0.15937(17) 0.70749(16) -0.06945(15) 0.0232(4) Uani 1 1 d . . . N2 N 0.30131(16) 0.65583(15) 0.10795(14) 0.0215(3) Uani 1 1 d . . . N3 N 0.44132(17) 0.91936(16) 0.19073(15) 0.0242(4) Uani 1 1 d . . . Ni Ni 0.27354(3) 0.80662(2) 0.08491(2) 0.02241(7) 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 C1 0.0378(13) 0.0282(11) 0.0318(12) 0.0146(9) -0.0001(10) 0.0087(9) C2 0.0240(10) 0.0286(11) 0.0242(10) 0.0117(9) 0.0043(8) 0.0095(8) C3 0.0240(10) 0.0311(11) 0.0230(10) 0.0113(9) 0.0048(8) 0.0101(9) C4 0.0215(10) 0.0288(11) 0.0224(10) 0.0079(9) 0.0035(8) 0.0080(8) C5 0.0198(10) 0.0222(10) 0.0204(10) 0.0060(8) 0.0038(8) 0.0062(8) C6 0.0216(10) 0.0207(10) 0.0224(10) 0.0065(8) 0.0050(8) 0.0061(8) C7 0.0230(10) 0.0199(9) 0.0219(10) 0.0076(8) 0.0049(8) 0.0075(8) C8 0.0242(10) 0.0217(10) 0.0229(10) 0.0094(8) 0.0067(8) 0.0078(8) C9 0.0223(10) 0.0222(10) 0.0230(10) 0.0101(8) 0.0047(8) 0.0078(8) C10 0.0217(10) 0.0214(10) 0.0215(10) 0.0075(8) 0.0030(8) 0.0083(8) C11 0.0215(10) 0.0257(10) 0.0217(10) 0.0086(8) 0.0019(8) 0.0087(8) C12 0.0201(10) 0.0233(10) 0.0225(10) 0.0060(8) 0.0018(8) 0.0074(8) C13 0.0211(10) 0.0235(10) 0.0265(11) 0.0051(8) 0.0044(8) 0.0068(8) C14 0.0227(10) 0.0231(10) 0.0291(11) 0.0063(9) 0.0044(8) 0.0050(8) C15 0.0252(11) 0.0220(10) 0.0292(11) 0.0082(9) 0.0042(9) 0.0073(8) C16 0.0424(14) 0.0254(11) 0.0416(13) 0.0157(10) -0.0035(11) 0.0062(10) C17 0.0284(11) 0.0398(12) 0.0240(11) 0.0145(9) 0.0018(9) 0.0096(10) C18 0.0346(13) 0.0507(15) 0.0349(13) 0.0174(11) 0.0014(10) 0.0171(11) C19 0.0270(11) 0.0290(11) 0.0258(11) 0.0061(9) -0.0045(9) 0.0039(9) C20 0.0417(13) 0.0326(12) 0.0251(11) 0.0045(9) 0.0025(10) 0.0094(10) C21 0.0319(11) 0.0193(10) 0.0268(11) 0.0100(8) 0.0031(9) 0.0063(8) C22 0.0527(15) 0.0232(11) 0.0364(13) 0.0064(10) 0.0120(11) 0.0118(10) C23 0.0267(11) 0.0238(10) 0.0281(11) 0.0129(9) 0.0028(8) 0.0094(8) C24 0.0277(12) 0.0484(15) 0.0565(16) 0.0326(13) 0.0100(11) 0.0166(11) C25 0.0289(11) 0.0286(11) 0.0273(11) 0.0056(9) -0.0026(9) 0.0055(9) C26 0.0347(14) 0.0604(17) 0.0442(15) 0.0057(13) -0.0074(11) 0.0227(13) C27 0.0306(12) 0.0234(11) 0.0330(12) 0.0068(9) 0.0008(9) 0.0009(9) C28 0.0549(16) 0.0290(12) 0.0366(13) 0.0041(10) 0.0093(12) 0.0109(11) I 0.03378(10) 0.03312(9) 0.03564(10) 0.00881(7) 0.00602(6) 0.01524(7) N1 0.0246(9) 0.0230(8) 0.0226(9) 0.0088(7) 0.0021(7) 0.0082(7) N2 0.0220(8) 0.0191(8) 0.0224(8) 0.0070(7) 0.0008(7) 0.0065(7) N3 0.0242(9) 0.0208(8) 0.0266(9) 0.0082(7) 0.0007(7) 0.0069(7) Ni 0.02417(14) 0.01734(13) 0.02339(14) 0.00627(10) -0.00270(10) 0.00658(10) _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 C1 C2 1.491(3) . ? C2 N1 1.328(3) . ? C2 C3 1.440(3) . ? C3 C4 1.366(3) . ? C3 C17 1.504(3) . ? C4 C5 1.444(3) . ? C4 C19 1.499(3) . ? C5 C6 1.366(3) . ? C5 N1 1.412(3) . ? C6 C7 1.418(3) . ? C7 N2 1.365(3) . ? C7 C8 1.432(3) . ? C8 C9 1.382(3) . ? C8 C21 1.502(3) . ? C9 C10 1.429(3) . ? C9 C23 1.504(3) . ? C10 N2 1.368(3) . ? C10 C11 1.411(3) . ? C11 C12 1.370(3) . ? C12 N3 1.405(3) . ? C12 C13 1.447(3) . ? C13 C14 1.372(3) . ? C13 C25 1.492(3) . ? C14 C15 1.437(3) . ? C14 C27 1.506(3) . ? C15 N3 1.329(3) . ? C15 C16 1.489(3) . ? C17 C18 1.516(3) . ? C19 C20 1.527(3) . ? C21 C22 1.521(3) . ? C23 C24 1.520(3) . ? C25 C26 1.521(3) . ? C27 C28 1.512(3) . ? I Ni 2.5854(3) . ? N1 Ni 1.9664(17) . ? N2 Ni 1.9397(16) . ? N3 Ni 1.9732(17) . ? 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 C2 C3 111.53(18) . . ? N1 C2 C1 121.86(19) . . ? C3 C2 C1 126.61(19) . . ? C4 C3 C2 106.58(18) . . ? C4 C3 C17 128.4(2) . . ? C2 C3 C17 125.06(19) . . ? C3 C4 C5 106.84(18) . . ? C3 C4 C19 128.06(19) . . ? C5 C4 C19 125.00(19) . . ? C6 C5 N1 124.23(18) . . ? C6 C5 C4 127.09(19) . . ? N1 C5 C4 108.55(17) . . ? C5 C6 C7 127.28(19) . . ? N2 C7 C6 122.62(18) . . ? N2 C7 C8 110.14(17) . . ? C6 C7 C8 127.06(18) . . ? C9 C8 C7 106.28(17) . . ? C9 C8 C21 128.33(18) . . ? C7 C8 C21 125.26(18) . . ? C8 C9 C10 106.75(17) . . ? C8 C9 C23 127.77(18) . . ? C10 C9 C23 125.22(18) . . ? N2 C10 C11 122.44(18) . . ? N2 C10 C9 109.91(17) . . ? C11 C10 C9 127.63(18) . . ? C12 C11 C10 127.73(19) . . ? C11 C12 N3 124.15(18) . . ? C11 C12 C13 126.82(19) . . ? N3 C12 C13 108.94(17) . . ? C14 C13 C12 106.31(18) . . ? C14 C13 C25 128.32(19) . . ? C12 C13 C25 125.34(19) . . ? C13 C14 C15 106.68(18) . . ? C13 C14 C27 128.3(2) . . ? C15 C14 C27 124.97(19) . . ? N3 C15 C14 111.59(18) . . ? N3 C15 C16 121.92(19) . . ? C14 C15 C16 126.48(19) . . ? C3 C17 C18 114.15(19) . . ? C4 C19 C20 112.69(18) . . ? C8 C21 C22 112.94(18) . . ? C9 C23 C24 112.59(18) . . ? C13 C25 C26 112.8(2) . . ? C14 C27 C28 112.8(2) . . ? C2 N1 C5 106.44(17) . . ? C2 N1 Ni 129.71(14) . . ? C5 N1 Ni 123.53(13) . . ? C7 N2 C10 106.90(16) . . ? C7 N2 Ni 126.82(13) . . ? C10 N2 Ni 126.26(13) . . ? C15 N3 C12 106.47(17) . . ? C15 N3 Ni 129.52(14) . . ? C12 N3 Ni 121.90(13) . . ? N2 Ni N1 93.33(7) . . ? N2 Ni N3 93.69(7) . . ? N1 Ni N3 153.71(7) . . ? N2 Ni I 115.57(5) . . ? N1 Ni I 101.49(5) . . ? N3 Ni I 98.21(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 2.5(2) . . . . ? C1 C2 C3 C4 -177.3(2) . . . . ? N1 C2 C3 C17 -176.33(19) . . . . ? C1 C2 C3 C17 4.0(3) . . . . ? C2 C3 C4 C5 -2.0(2) . . . . ? C17 C3 C4 C5 176.7(2) . . . . ? C2 C3 C4 C19 -178.6(2) . . . . ? C17 C3 C4 C19 0.1(4) . . . . ? C3 C4 C5 C6 -174.8(2) . . . . ? C19 C4 C5 C6 1.9(3) . . . . ? C3 C4 C5 N1 1.1(2) . . . . ? C19 C4 C5 N1 177.79(19) . . . . ? N1 C5 C6 C7 -3.8(3) . . . . ? C4 C5 C6 C7 171.5(2) . . . . ? C5 C6 C7 N2 6.0(3) . . . . ? C5 C6 C7 C8 -168.6(2) . . . . ? N2 C7 C8 C9 -0.3(2) . . . . ? C6 C7 C8 C9 174.91(19) . . . . ? N2 C7 C8 C21 -176.43(19) . . . . ? C6 C7 C8 C21 -1.2(3) . . . . ? C7 C8 C9 C10 0.8(2) . . . . ? C21 C8 C9 C10 176.8(2) . . . . ? C7 C8 C9 C23 -173.57(19) . . . . ? C21 C8 C9 C23 2.4(4) . . . . ? C8 C9 C10 N2 -1.0(2) . . . . ? C23 C9 C10 N2 173.49(18) . . . . ? C8 C9 C10 C11 -179.4(2) . . . . ? C23 C9 C10 C11 -4.8(3) . . . . ? N2 C10 C11 C12 -7.6(3) . . . . ? C9 C10 C11 C12 170.5(2) . . . . ? C10 C11 C12 N3 -1.6(3) . . . . ? C10 C11 C12 C13 -178.0(2) . . . . ? C11 C12 C13 C14 175.9(2) . . . . ? N3 C12 C13 C14 -0.9(2) . . . . ? C11 C12 C13 C25 -2.4(3) . . . . ? N3 C12 C13 C25 -179.20(19) . . . . ? C12 C13 C14 C15 0.9(2) . . . . ? C25 C13 C14 C15 179.1(2) . . . . ? C12 C13 C14 C27 179.4(2) . . . . ? C25 C13 C14 C27 -2.4(4) . . . . ? C13 C14 C15 N3 -0.6(3) . . . . ? C27 C14 C15 N3 -179.2(2) . . . . ? C13 C14 C15 C16 179.0(2) . . . . ? C27 C14 C15 C16 0.4(4) . . . . ? C4 C3 C17 C18 93.3(3) . . . . ? C2 C3 C17 C18 -88.2(3) . . . . ? C3 C4 C19 C20 101.3(3) . . . . ? C5 C4 C19 C20 -74.8(3) . . . . ? C9 C8 C21 C22 -94.2(3) . . . . ? C7 C8 C21 C22 81.1(3) . . . . ? C8 C9 C23 C24 94.7(3) . . . . ? C10 C9 C23 C24 -78.6(3) . . . . ? C14 C13 C25 C26 -97.4(3) . . . . ? C12 C13 C25 C26 80.4(3) . . . . ? C13 C14 C27 C28 -96.2(3) . . . . ? C15 C14 C27 C28 82.1(3) . . . . ? C3 C2 N1 C5 -1.8(2) . . . . ? C1 C2 N1 C5 177.98(19) . . . . ? C3 C2 N1 Ni -175.38(14) . . . . ? C1 C2 N1 Ni 4.4(3) . . . . ? C6 C5 N1 C2 176.50(19) . . . . ? C4 C5 N1 C2 0.4(2) . . . . ? C6 C5 N1 Ni -9.4(3) . . . . ? C4 C5 N1 Ni 174.56(13) . . . . ? C6 C7 N2 C10 -175.80(18) . . . . ? C8 C7 N2 C10 -0.4(2) . . . . ? C6 C7 N2 Ni 5.8(3) . . . . ? C8 C7 N2 Ni -178.77(13) . . . . ? C11 C10 N2 C7 179.27(18) . . . . ? C9 C10 N2 C7 0.8(2) . . . . ? C11 C10 N2 Ni -2.3(3) . . . . ? C9 C10 N2 Ni 179.28(13) . . . . ? C14 C15 N3 C12 0.0(2) . . . . ? C16 C15 N3 C12 -179.6(2) . . . . ? C14 C15 N3 Ni 163.35(15) . . . . ? C16 C15 N3 Ni -16.3(3) . . . . ? C11 C12 N3 C15 -176.3(2) . . . . ? C13 C12 N3 C15 0.6(2) . . . . ? C11 C12 N3 Ni 18.7(3) . . . . ? C13 C12 N3 Ni -164.34(13) . . . . ? C7 N2 Ni N1 -13.52(17) . . . . ? C10 N2 Ni N1 168.35(17) . . . . ? C7 N2 Ni N3 -168.17(17) . . . . ? C10 N2 Ni N3 13.70(17) . . . . ? C7 N2 Ni I 90.90(16) . . . . ? C10 N2 Ni I -87.22(16) . . . . ? C2 N1 Ni N2 -172.43(19) . . . . ? C5 N1 Ni N2 14.91(16) . . . . ? C2 N1 Ni N3 -67.2(3) . . . . ? C5 N1 Ni N3 120.18(18) . . . . ? C2 N1 Ni I 70.63(18) . . . . ? C5 N1 Ni I -102.03(15) . . . . ? C15 N3 Ni N2 177.83(19) . . . . ? C12 N3 Ni N2 -21.03(16) . . . . ? C15 N3 Ni N1 72.6(3) . . . . ? C12 N3 Ni N1 -126.22(18) . . . . ? C15 N3 Ni I -65.66(19) . . . . ? C12 N3 Ni I 95.47(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.387 _refine_diff_density_min -0.586 _refine_diff_density_rms 0.066