Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_a20 _database_code_CSD 162662 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Kryatov, Sergey V.' 'Nazarenko, Alexander Y.' 'Rybak-Akimova, Elena V.' 'Smith, Millicent B.' _publ_contact_author_name 'Dr Elena V Rybak-Akimova' _publ_contact_author_address ; Dr Elena V Rybak-Akimova Department of Chemistry Tufts University Medford Massachusetts 02155 UNITED STATES OF AMERICA ; _publ_contact_author_email 'ERYBAKAK@EMERALD.TUFTS.EDU' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H20 N6 Ni O2' _chemical_formula_weight 291.01 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' 'Ni' 'Ni' 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.040(3) _cell_length_b 14.150(3) _cell_length_c 7.4400(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1372.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 1.415 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1823 _diffrn_reflns_av_R_equivalents 0.0098 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 27.56 _reflns_number_total 1589 _reflns_number_gt 1048 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.2123P] 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 1589 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.0000 0.0000 0.03203(16) Uani 1 d S . . N1 N 0.35968(16) -0.00265(12) 0.0369(3) 0.0381(4) Uani 1 d . . . N3 N 0.31365(14) 0.15621(12) -0.0169(2) 0.0385(4) Uani 1 d . . . N2 N 0.49099(13) 0.12757(14) -0.0518(3) 0.0380(4) Uani 1 d . . . C4 C 0.41166(16) 0.18271(14) -0.0487(3) 0.0352(5) Uani 1 d . . . C2 C 0.29256(17) 0.06450(15) 0.0234(3) 0.0365(5) Uani 1 d . . . C3 C 0.18088(19) 0.04373(19) 0.0515(5) 0.0518(6) Uani 1 d . . . C5 C 0.4264(2) 0.28724(16) -0.0789(4) 0.0470(6) Uani 1 d . . . O1 O 0.69217(15) 0.20539(15) -0.1637(3) 0.0573(5) Uani 1 d . . . H5A H 0.371(2) 0.3105(16) -0.138(4) 0.052(7) Uiso 1 d . . . H5B H 0.484(2) 0.302(2) -0.146(5) 0.071(9) Uiso 1 d . . . H2A H 0.5479(19) 0.1535(16) -0.085(4) 0.046(7) Uiso 1 d . . . H3A H 0.168(3) -0.018(3) 0.104(5) 0.101(12) Uiso 1 d . . . H11A H 0.717(3) 0.196(2) -0.253(5) 0.086(13) Uiso 1 d . . . H3B H 0.142(4) 0.054(3) -0.059(7) 0.138(16) Uiso 1 d . . . H3C H 0.159(2) 0.082(2) 0.141(4) 0.091(11) Uiso 1 d . . . H1A H 0.3339(19) -0.0515(19) 0.067(4) 0.046(7) Uiso 1 d . . . H11B H 0.716(2) 0.242(2) -0.111(5) 0.064(10) Uiso 1 d . . . H5C H 0.420(3) 0.317(2) 0.027(5) 0.080(11) Uiso 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 0.0307(2) 0.0257(2) 0.0397(3) 0.00170(14) 0.00169(15) 0.00109(13) N1 0.0336(10) 0.0275(9) 0.0530(12) 0.0056(8) 0.0040(8) -0.0002(7) N3 0.0359(9) 0.0316(9) 0.0480(12) 0.0023(7) -0.0002(8) 0.0043(7) N2 0.0336(9) 0.0295(9) 0.0510(11) 0.0022(9) 0.0032(8) -0.0002(7) C4 0.0408(11) 0.0273(10) 0.0375(11) -0.0002(8) -0.0036(10) 0.0008(8) C2 0.0354(10) 0.0331(11) 0.0409(12) -0.0013(9) -0.0003(9) 0.0005(8) C3 0.0369(12) 0.0448(15) 0.0738(18) 0.0075(14) 0.0068(13) 0.0005(11) C5 0.0480(14) 0.0303(11) 0.0626(17) 0.0067(12) -0.0020(13) 0.0010(10) O1 0.0518(11) 0.0528(11) 0.0672(13) -0.0165(10) 0.0175(10) -0.0209(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 Ni1 N2 1.849(2) 5_655 ? Ni1 N2 1.849(2) . ? Ni1 N1 1.851(2) . ? Ni1 N1 1.851(2) 5_655 ? N1 C2 1.296(3) . ? N1 H1A 0.80(3) . ? N3 C4 1.353(3) . ? N3 C2 1.360(3) . ? N2 C4 1.296(3) . ? N2 H2A 0.86(3) . ? C4 C5 1.508(3) . ? C2 C3 1.500(3) . ? C3 H3A 0.98(4) . ? C3 H3B 0.98(5) . ? C3 H3C 0.91(3) . ? C5 H5A 0.91(3) . ? C5 H5B 0.93(3) . ? C5 H5C 0.90(4) . ? O1 H11A 0.75(4) . ? O1 H11B 0.72(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni1 N2 180.0 5_655 . ? N2 Ni1 N1 90.69(8) 5_655 . ? N2 Ni1 N1 89.31(8) . . ? N2 Ni1 N1 89.31(8) 5_655 5_655 ? N2 Ni1 N1 90.69(8) . 5_655 ? N1 Ni1 N1 180.0 . 5_655 ? C2 N1 Ni1 129.90(17) . . ? C2 N1 H1A 111.8(17) . . ? Ni1 N1 H1A 118.3(17) . . ? C4 N3 C2 119.62(18) . . ? C4 N2 Ni1 129.40(16) . . ? C4 N2 H2A 115.8(15) . . ? Ni1 N2 H2A 114.8(15) . . ? N2 C4 N3 126.17(19) . . ? N2 C4 C5 119.1(2) . . ? N3 C4 C5 114.71(19) . . ? N1 C2 N3 125.5(2) . . ? N1 C2 C3 120.1(2) . . ? N3 C2 C3 114.46(19) . . ? C2 C3 H3A 113(2) . . ? C2 C3 H3B 111(3) . . ? H3A C3 H3B 112(4) . . ? C2 C3 H3C 107(2) . . ? H3A C3 H3C 101(3) . . ? H3B C3 H3C 111(3) . . ? C4 C5 H5A 109.0(15) . . ? C4 C5 H5B 113.4(18) . . ? H5A C5 H5B 108(2) . . ? C4 C5 H5C 108(2) . . ? H5A C5 H5C 101(3) . . ? H5B C5 H5C 116(3) . . ? H11A O1 H11B 115(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 N2 Ni1 N1 C2 -179.1(2) 5_655 . . . ? N2 Ni1 N1 C2 0.9(2) . . . . ? N1 Ni1 N1 C2 93(15) 5_655 . . . ? N2 Ni1 N2 C4 -145(28) 5_655 . . . ? N1 Ni1 N2 C4 2.5(2) . . . . ? N1 Ni1 N2 C4 -177.5(2) 5_655 . . . ? Ni1 N2 C4 N3 -4.7(4) . . . . ? Ni1 N2 C4 C5 173.87(19) . . . . ? C2 N3 C4 N2 2.8(3) . . . . ? C2 N3 C4 C5 -175.8(2) . . . . ? Ni1 N1 C2 N3 -2.6(4) . . . . ? Ni1 N1 C2 C3 176.9(2) . . . . ? C4 N3 C2 N1 0.9(3) . . . . ? C4 N3 C2 C3 -178.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.867 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.867 _refine_diff_density_max 0.543 _refine_diff_density_min -0.531 _refine_diff_density_rms 0.076