# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Nov 11 13:10:21 2002' _audit_creation_method 'PLATON option' _audit_update_record ; ? ; #=============================================================================== # 1. SUBMISSION DETAILS _journal_coden_Cambridge 440 _publ_section_title ; The binding mode of the ambidentate ligand dicyanamide to transition metal ions can be tuned by bisimidazoline ligands with a H-bonding donor property at the rear side of the ligand. ; loop_ _publ_author_name 'Aminou Mohamadou' 'van Albada,Gerard A.' 'Huub Kooijman' 'Birgit Wieczorek' 'Anthony L. Spek' 'Jan Reedijk' _publ_contact_author_name 'Prof Jan Reedijk' _publ_contact_author_address ; Gorlaeus Laboratories Leiden Institute of Chemistry P.O. Box 9502 Leiden 2300 RA NETHERLANDS ; _publ_contact_author_email REEDIJK@CHEM.LEIDENUNIV.NL _publ_requested_journal 'New Journal of Chemistry' #=============================================================================== # 4. TEXT _publ_section_references ; Nonius (1998). Collect Software, Nonius B.V., Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C.W. Carter & R.M. Sweet, pp. 307-326. London: Academic Press. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of Gottingen, Germany, 1997. Sheldrick, G.M. SHELXS86. Program for Crystal Structure solution. University of Gottingen, Germany, 1986. Sheldrick, G.M. SHELXS97. Program for Crystal Structure solution. University of Gottingen, Germany, 1997. Wilson, A.J.C. (1992) Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_acknowledgements ; This work was supported in part (ALS) by the Council for the Chemical Sciences of the Netherlands Organization for Scientific Research (CW-NWO). ; #=============================================================================== data_1 _database_code_CSD 206278 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(Cu 2+), (C6 H10 N4), 2(C2 N3 1-)' _chemical_formula_structural ? _chemical_formula_sum 'C10 H10 Cu N10' _chemical_formula_iupac ? _chemical_formula_weight 333.83 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 7.9536(10) _cell_length_b 6.7856(10) _cell_length_c 24.295(4) _cell_angle_alpha 90 _cell_angle_beta 92.585(12) _cell_angle_gamma 90 _cell_volume 1309.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 210 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _cell_special_details ; Quoted _cell_measurement_* data items refer to the initial cell determination. The cell parameters as reported in _cell_* are based on the complete data set. ; _exptl_crystal_description 'plate ' _exptl_crystal_colour 'turquoise ' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.010 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.692 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 1.678 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type 'multi-scan ' _exptl_absorpt_process_details '(Spek, 2002)' _exptl_absorpt_correction_T_min 0.875 _exptl_absorpt_correction_T_max 0.986 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD area detector' _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 25911 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 3011 _reflns_number_gt 2481 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'Denzo (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'PLATON (Spek, 2002)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2 > 2sigma(F^2) is used only for calculating -R-factor-obs 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 'w=1/[\s^2^(F~o~^2^)+(0.0381P)^2^+0.36P] where P=(F~o~^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct ' _atom_sites_solution_secondary 'difmap ' _atom_sites_solution_hydrogens 'difmap ' _refine_ls_hydrogen_treatment 'refall ' _refine_ls_extinction_method 'none ' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack none _refine_ls_number_reflns 3011 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0714 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.333 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.064 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cu Cu Uani 0.25914(3) 0.01252(3) 0.31344(1) 1.000 0.0206(1) . . N1 N Uani 0.0354(2) -0.3354(3) 0.18065(6) 1.000 0.0338(5) . . N2 N Uani 0.0920(2) -0.2504(3) 0.08452(7) 1.000 0.0357(6) . . N3 N Uani 0.1837(2) -0.1949(3) 0.26186(7) 1.000 0.0325(5) . . N4 N Uani 0.4222(2) 0.3769(3) 0.17561(7) 1.000 0.0334(5) . . N5 N Uani 0.3202(2) 0.1858(3) 0.25273(6) 1.000 0.0306(5) . . N6 N Uani 0.3446(2) 0.3472(3) 0.07678(6) 1.000 0.0306(5) . . N11 N Uani 0.19320(18) -0.1346(2) 0.37968(6) 1.000 0.0191(4) . . N12 N Uani 0.1786(2) -0.1343(3) 0.47113(7) 1.000 0.0288(5) . . N21 N Uani 0.35206(18) 0.1927(2) 0.37130(6) 1.000 0.0186(4) . . N22 N Uani 0.4021(2) 0.2426(3) 0.46147(7) 1.000 0.0288(5) . . C1 C Uani 0.0727(2) -0.2852(3) 0.13009(8) 1.000 0.0246(6) . . C2 C Uani 0.1178(2) -0.2563(3) 0.22219(8) 1.000 0.0254(6) . . C3 C Uani 0.3619(2) 0.2699(3) 0.21473(8) 1.000 0.0250(6) . . C4 C Uani 0.3735(2) 0.3530(3) 0.12382(7) 1.000 0.0219(5) . . C13 C Uani 0.2321(2) -0.0490(3) 0.42605(7) 1.000 0.0194(5) . . C14 C Uani 0.0778(3) -0.3079(3) 0.45476(8) 1.000 0.0278(6) . . C15 C Uani 0.0860(3) -0.3057(3) 0.39126(8) 1.000 0.0263(6) . . C23 C Uani 0.3304(2) 0.1347(3) 0.42122(7) 1.000 0.0186(5) . . C24 C Uani 0.4885(3) 0.4096(3) 0.43654(8) 1.000 0.0266(6) . . C25 C Uani 0.4648(3) 0.3649(3) 0.37411(8) 1.000 0.0251(6) . . H12 H Uiso 0.183(3) -0.088(4) 0.5015(11) 1.000 0.063(9) . . H14A H Uiso -0.031(3) -0.293(3) 0.4661(9) 1.000 0.037(6) . . H14B H Uiso 0.131(2) -0.429(3) 0.4708(8) 1.000 0.023(5) . . H15A H Uiso -0.018(3) -0.284(3) 0.3738(9) 1.000 0.043(7) . . H15B H Uiso 0.134(3) -0.430(3) 0.3771(9) 1.000 0.030(5) . . H22 H Uiso 0.392(3) 0.222(3) 0.4950(9) 1.000 0.028(6) . . H24A H Uiso 0.434(3) 0.533(3) 0.4469(9) 1.000 0.027(6) . . H24B H Uiso 0.609(3) 0.415(3) 0.4474(8) 1.000 0.029(5) . . H25A H Uiso 0.413(3) 0.474(3) 0.3562(9) 1.000 0.023(5) . . H25B H Uiso 0.567(3) 0.337(3) 0.3569(9) 1.000 0.041(6) . . 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 Cu 0.0289(1) 0.0240(1) 0.0087(1) 0.0001(1) 0.0003(1) -0.0076(1) N1 0.0377(9) 0.0480(11) 0.0153(8) -0.0047(8) -0.0016(7) -0.0182(9) N2 0.0403(10) 0.0460(11) 0.0210(9) -0.0039(8) 0.0036(7) -0.0033(9) N3 0.0417(10) 0.0390(10) 0.0169(8) -0.0058(8) 0.0009(7) -0.0150(8) N4 0.0449(10) 0.0412(10) 0.0142(8) 0.0049(7) 0.0010(7) -0.0185(8) N5 0.0393(10) 0.0368(10) 0.0157(8) 0.0039(8) 0.0007(7) -0.0106(8) N6 0.0375(9) 0.0368(10) 0.0174(9) 0.0024(7) 0.0012(7) -0.0044(8) N11 0.0227(7) 0.0206(7) 0.0141(7) 0.0023(6) 0.0012(6) -0.0018(6) N12 0.0410(10) 0.0326(9) 0.0132(9) 0.0031(7) 0.0044(7) -0.0064(8) N21 0.0218(7) 0.0200(7) 0.0138(7) -0.0008(6) 0.0001(6) -0.0028(6) N22 0.0425(10) 0.0323(9) 0.0114(8) -0.0047(7) -0.0001(7) -0.0079(8) C1 0.0235(9) 0.0273(10) 0.0228(10) -0.0061(8) -0.0011(7) -0.0017(8) C2 0.0313(10) 0.0277(10) 0.0176(10) 0.0001(8) 0.0053(8) -0.0058(8) C3 0.0285(10) 0.0295(10) 0.0169(9) -0.0019(8) -0.0001(7) -0.0037(8) C4 0.0241(9) 0.0220(9) 0.0200(10) 0.0027(8) 0.0056(7) -0.0006(8) C13 0.0212(9) 0.0239(9) 0.0131(9) 0.0026(7) 0.0012(7) 0.0034(7) C14 0.0281(10) 0.0308(11) 0.0248(11) 0.0077(9) 0.0061(8) -0.0014(9) C15 0.0287(10) 0.0238(10) 0.0265(11) 0.0046(8) 0.0024(8) -0.0066(8) C23 0.0205(9) 0.0212(9) 0.0142(9) -0.0022(7) 0.0003(7) 0.0035(7) C24 0.0301(10) 0.0272(10) 0.0224(10) -0.0067(8) -0.0014(8) -0.0047(9) C25 0.0299(10) 0.0233(10) 0.0221(10) -0.0018(8) 0.0009(8) -0.0069(8) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N3 1.9605(19) . . yes Cu N5 1.9643(17) . . yes Cu N11 1.9843(15) . . yes Cu N21 1.9807(15) . . yes Cu N1 2.5698(17) . 2_555 yes N1 C1 1.321(2) . . yes N1 C2 1.295(2) . . yes N2 C1 1.149(3) . . yes N3 C2 1.154(3) . . yes N4 C3 1.304(3) . . yes N4 C4 1.310(2) . . yes N5 C3 1.147(3) . . yes N6 C4 1.156(2) . . yes N11 C13 1.293(2) . . yes N11 C15 1.475(3) . . yes N12 C13 1.326(2) . . yes N12 C14 1.470(3) . . yes N21 C23 1.294(2) . . yes N21 C25 1.473(3) . . yes N22 C23 1.329(3) . . yes N22 C24 1.470(3) . . yes N12 H12 0.80(3) . . no N22 H22 0.83(2) . . no C13 C23 1.479(3) . . no C14 C15 1.547(3) . . no C24 C25 1.550(3) . . no C14 H14A 0.93(2) . . no C14 H14B 1.00(2) . . no C15 H15A 0.92(2) . . no C15 H15B 0.99(2) . . no C24 H24A 0.98(2) . . no C24 H24B 0.98(2) . . no C25 H25A 0.94(2) . . no C25 H25B 0.95(2) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu N5 91.64(8) . . . yes N3 Cu N11 94.17(7) . . . yes N3 Cu N21 172.06(7) . . . yes N1 Cu N3 94.04(6) 2_555 . . yes N5 Cu N11 173.43(7) . . . yes N5 Cu N21 93.81(7) . . . yes N1 Cu N5 93.35(6) 2_555 . . yes N11 Cu N21 80.72(6) . . . yes N1 Cu N11 83.21(6) 2_555 . . yes N1 Cu N21 91.40(6) 2_555 . . yes C1 N1 C2 119.39(18) . . . yes Cu N3 C2 155.16(18) . . . yes C3 N4 C4 121.90(18) . . . yes Cu N4 C3 119.51(12) 2_655 . . yes Cu N4 C4 111.88(12) 2_655 . . yes Cu N5 C3 172.96(18) . . . yes Cu N11 C13 114.78(12) . . . yes Cu N11 C15 136.62(12) . . . yes C13 N11 C15 107.77(15) . . . yes C13 N12 C14 108.54(16) . . . yes Cu N21 C23 114.60(12) . . . yes Cu N21 C25 136.85(12) . . . yes C23 N21 C25 107.72(15) . . . yes C23 N22 C24 108.33(16) . . . yes C14 N12 H12 124.3(18) . . . no C13 N12 H12 126.0(19) . . . no C24 N22 H22 126.8(15) . . . no C23 N22 H22 124.7(15) . . . no N1 C1 N2 173.8(2) . . . yes N1 C2 N3 174.6(2) . . . yes N4 C3 N5 173.0(2) . . . yes N4 C4 N6 172.2(2) . . . yes N11 C13 C23 114.60(15) . . . yes N12 C13 C23 128.61(17) . . . yes N11 C13 N12 116.79(18) . . . yes N12 C14 C15 102.42(16) . . . yes N11 C15 C14 104.39(16) . . . yes N21 C23 N22 116.82(17) . . . yes N22 C23 C13 128.07(16) . . . yes N21 C23 C13 115.08(15) . . . yes N22 C24 C25 102.35(16) . . . yes N21 C25 C24 104.33(16) . . . yes N12 C14 H14A 109.7(13) . . . no N12 C14 H14B 109.8(11) . . . no C15 C14 H14A 112.2(14) . . . no C15 C14 H14B 111.2(11) . . . no H14A C14 H14B 111.1(16) . . . no N11 C15 H15A 107.5(13) . . . no N11 C15 H15B 111.6(13) . . . no C14 C15 H15A 112.5(14) . . . no C14 C15 H15B 111.8(13) . . . no H15A C15 H15B 109.0(19) . . . no N22 C24 H24A 109.4(13) . . . no N22 C24 H24B 112.7(12) . . . no C25 C24 H24A 112.5(13) . . . no C25 C24 H24B 110.1(12) . . . no H24A C24 H24B 109.6(18) . . . no N21 C25 H25A 110.4(14) . . . no N21 C25 H25B 110.7(13) . . . no C24 C25 H25A 109.2(13) . . . no C24 C25 H25B 113.6(14) . . . no H25A C25 H25B 108.5(19) . . . no 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 N5 Cu N3 C2 -40.6(4) . . . . no N11 Cu N3 C2 136.3(4) . . . . no N1 Cu N3 C2 52.8(4) 2_555 . . . no N3 Cu N11 C13 176.20(13) . . . . no N3 Cu N11 C15 -15.85(19) . . . . no N21 Cu N11 C13 2.33(12) . . . . no N21 Cu N11 C15 170.27(19) . . . . no N1 Cu N11 C13 -90.21(13) 2_555 . . . no N1 Cu N11 C15 77.73(18) 2_555 . . . no N5 Cu N21 C23 177.10(13) . . . . no N5 Cu N21 C25 -14.94(19) . . . . no N11 Cu N21 C23 0.76(12) . . . . no N11 Cu N21 C25 168.72(19) . . . . no N1 Cu N21 C23 83.64(13) 2_555 . . . no N1 Cu N21 C25 -108.39(18) 2_555 . . . no N3 Cu N1 C1 137.66(15) . . 2_555 2_555 no N3 Cu N1 C2 -63.61(18) . . 2_555 2_555 no N5 Cu N1 C1 -130.45(15) . . 2_555 2_555 no N5 Cu N1 C2 28.28(18) . . 2_555 2_555 no N11 Cu N1 C1 43.93(15) . . 2_555 2_555 no N11 Cu N1 C2 -157.34(18) . . 2_555 2_555 no N21 Cu N1 C1 -36.55(15) . . 2_555 2_555 no N21 Cu N1 C2 122.17(17) . . 2_555 2_555 no Cu N11 C13 N12 174.78(13) . . . . no Cu N11 C13 C23 -4.64(19) . . . . no C15 N11 C13 N12 3.4(2) . . . . no C15 N11 C13 C23 -175.98(15) . . . . no Cu N11 C15 C14 -171.24(14) . . . . no C13 N11 C15 C14 -2.7(2) . . . . no C14 N12 C13 N11 -2.6(2) . . . . no C14 N12 C13 C23 176.75(18) . . . . no C13 N12 C14 C15 0.5(2) . . . . no Cu N21 C23 N22 174.84(13) . . . . no Cu N21 C23 C13 -3.34(19) . . . . no C25 N21 C23 N22 3.4(2) . . . . no C25 N21 C23 C13 -174.73(15) . . . . no Cu N21 C25 C24 -174.64(14) . . . . no C23 N21 C25 C24 -6.1(2) . . . . no C24 N22 C23 N21 1.1(2) . . . . no C24 N22 C23 C13 178.98(18) . . . . no C23 N22 C24 C25 -4.8(2) . . . . no N11 C13 C23 N21 5.4(2) . . . . no N11 C13 C23 N22 -172.58(18) . . . . no N12 C13 C23 N21 -173.99(18) . . . . no N12 C13 C23 N22 8.1(3) . . . . no N12 C14 C15 N11 1.3(2) . . . . no N22 C24 C25 N21 6.4(2) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cu N12 4.0375(19) . . no Cu N22 4.0368(19) . . no Cu N4 2.6982(17) . 2_645 no Cu C3 3.5284(18) . 2_645 no Cu C4 3.4103(18) . 2_645 no N1 Cu 2.5698(17) . 2_545 no N1 N11 3.055(2) . 2_545 no N1 N21 3.283(2) . 2_545 no N2 C13 3.280(3) . 2_545 no N2 C14 3.411(3) . 2_555 no N2 C15 3.396(3) . 2_555 no N2 C23 3.446(2) . 2_545 no N2 N12 2.974(2) . 4_544 no N2 C14 3.174(3) . 4_544 no N6 C24 3.275(3) . 2_645 no N6 N22 2.923(2) . 4_554 no N6 C13 3.443(2) . 2_655 no N6 C23 3.237(3) . 2_655 no N12 N2 2.974(2) . 4_545 no N12 N22 3.129(3) . . no N12 Cu 4.0375(19) . . no N21 N4 3.049(2) . 2_645 no N21 C4 3.173(2) . 2_645 no N22 N12 3.129(3) . . no N22 Cu 4.0368(19) . . no N22 N6 2.923(2) . 4_555 no N2 H24B 2.77(2) . 2_645 no N2 H12 2.43(3) . 4_544 no N6 H14A 2.82(2) . 2_555 no N6 H24A 2.84(2) . 2_645 no N6 H12 2.73(3) . 4_554 no N6 H22 2.09(2) . 4_554 no C1 C4 3.436(3) . 1_545 no C1 Cu 3.3255(18) . 2_545 no C1 N11 3.179(2) . 2_545 no C1 N21 3.380(2) . 2_545 no C1 C13 3.262(3) . 2_545 no C1 C15 3.520(3) . 2_555 no C1 C23 3.430(2) . 2_545 no C2 Cu 3.4589(18) . 2_545 no C4 C25 3.553(3) . 2_645 no C4 C13 3.478(2) . 2_655 no C4 C1 3.436(3) . 1_565 no C4 C23 3.260(3) . 2_655 no C4 C24 3.543(3) . 2_645 no C13 N6 3.443(2) . 2_645 no C13 C1 3.262(3) . 2_555 no C13 N2 3.280(3) . 2_555 no C13 C4 3.478(2) . 2_645 no C14 N2 3.174(3) . 4_545 no C14 N2 3.411(3) . 2_545 no C15 N2 3.396(3) . 2_545 no C15 C1 3.520(3) . 2_545 no C23 N6 3.237(3) . 2_645 no C23 C4 3.260(3) . 2_645 no C23 N2 3.446(2) . 2_555 no C23 C1 3.430(2) . 2_555 no C24 N6 3.275(3) . 2_655 no C24 C24 3.316(3) . 3_666 no C24 C4 3.543(3) . 2_655 no C25 C4 3.553(3) . 2_655 no C1 H25B 2.99(2) . 2_645 no C1 H15B 2.92(2) . 2_555 no C4 H15A 2.98(2) . 2_555 no C14 H14B 3.080(19) . 3_546 no C14 H24A 3.05(2) . 1_545 no C24 H24A 2.90(2) . 3_666 no C25 H15B 2.98(2) . 1_565 no H12 N2 2.43(3) . 4_545 no H12 N6 2.73(3) . 4_555 no H14A N6 2.82(2) . 2_545 no H14A H14B 2.58(3) . 3_546 no H14B H24A 2.52(3) . 1_545 no H14B C14 3.080(19) . 3_546 no H14B H14A 2.58(3) . 3_546 no H15A C4 2.98(2) . 2_545 no H15B C25 2.98(2) . 1_545 no H15B H25A 2.39(3) . 1_545 no H15B C1 2.92(2) . 2_545 no H22 H24A 2.55(3) . 3_666 no H22 N6 2.09(2) . 4_555 no H24A C14 3.05(2) . 1_565 no H24A H14B 2.52(3) . 1_565 no H24A N6 2.84(2) . 2_655 no H24A C24 2.90(2) . 3_666 no H24A H22 2.55(3) . 3_666 no H24B N2 2.77(2) . 2_655 no H25A H15B 2.39(3) . 1_565 no H25B C1 2.99(2) . 2_655 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N12 H12 N2 0.80(3) 2.43(3) 2.974(2) 126(2) 4_545 yes N22 H22 N6 0.83(2) 2.09(2) 2.923(2) 174(2) 4_555 yes #===END #=============================================================================== #=============================================================================== data_2 _database_code_CSD 206279 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(CU 2+), 2(C6 H10 N4), 2(C2 N3 1-)' _chemical_formula_structural ? _chemical_formula_sum 'C16 H20 Cu N14' _chemical_formula_iupac ? _chemical_formula_weight 472.01 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 6.5873(10) _cell_length_b 8.4512(10) _cell_length_c 9.2834(15) _cell_angle_alpha 67.977(12) _cell_angle_beta 81.207(13) _cell_angle_gamma 84.901(15) _cell_volume 473.19(13) _cell_formula_units_Z 1 _cell_measurement_temperature 150 _cell_measurement_reflns_used 104 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _cell_special_details ; Quoted _cell_measurement_* data items refer to the initial cell determination. The cell parameters as reported in _cell_* are based on the complete data set. ; _exptl_crystal_description plate _exptl_crystal_colour light-blue _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.080 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 243 _exptl_absorpt_coefficient_mu 1.194 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # cylinder 'cylindrical' # empirical 'empirical from intensities' # gaussian 'Gaussian from crystal shape' # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # refdelf 'refined from delta-F' # sphere 'spherical' _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Spek, 2002)' _exptl_absorpt_correction_T_min 0.826 _exptl_absorpt_correction_T_max 0.909 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD area detector' _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 10285 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 2155 _reflns_number_gt 1963 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'Denzo (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'PLATON (Spek, 2002)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2 > 2sigma(F^2) is used only for calculating -R-factor-obs 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 'w=1/[\s^2^(F~o~^2^)+(0.0347P)^2^+0.24P] where P=(F~o~^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct ' _atom_sites_solution_secondary 'difmap ' _atom_sites_solution_hydrogens 'difmap ' _refine_ls_hydrogen_treatment 'mixed ' _refine_ls_extinction_method 'none ' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack none _refine_ls_number_reflns 2155 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0752 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.739 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.062 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cu1 Cu Uani 0.00000 0.50000 0.50000 1.000 0.0169(1) . . N1 N Uani 0.1576(3) 0.2193(2) 0.4682(2) 1.000 0.0349(6) . . N2 N Uani 0.3070(3) 0.0108(3) 0.6944(2) 1.000 0.0383(7) . . N3 N Uani 0.1425(3) 0.2182(2) 0.20618(19) 1.000 0.0271(5) . . N11 N Uani -0.1352(2) 0.34001(19) 0.70432(17) 1.000 0.0161(4) . . N12 N Uani -0.1069(2) 0.2007(2) 0.95873(18) 1.000 0.0208(5) . . N21 N Uani 0.1956(2) 0.51451(19) 0.63949(17) 1.000 0.0160(4) . . N22 N Uani 0.2491(2) 0.4455(2) 0.88865(19) 1.000 0.0220(5) . . C1 C Uani 0.2382(3) 0.0997(3) 0.5846(2) 1.000 0.0218(6) . . C2 C Uani 0.1534(3) 0.2069(2) 0.3326(2) 1.000 0.0203(5) . . C13 C Uani -0.0380(3) 0.3182(2) 0.8222(2) 1.000 0.0148(5) . . C14 C Uani -0.2923(3) 0.1290(2) 0.9401(2) 1.000 0.0196(5) . . C15 C Uani -0.2938(3) 0.2089(2) 0.7606(2) 1.000 0.0190(5) . . C23 C Uani 0.1420(3) 0.4267(2) 0.7860(2) 1.000 0.0152(5) . . C24 C Uani 0.4080(3) 0.5704(2) 0.8029(2) 1.000 0.0192(5) . . C25 C Uani 0.3663(3) 0.6227(2) 0.6309(2) 1.000 0.0195(5) . . H12 H Uiso -0.067(4) 0.184(3) 1.036(3) 1.000 0.0310 . . H14A H Uiso -0.41710 0.16400 0.99660 1.000 0.0240 calc R H14B H Uiso -0.28100 0.00280 0.97750 1.000 0.0240 calc R H15A H Uiso -0.25900 0.12140 0.71280 1.000 0.0230 calc R H15B H Uiso -0.43050 0.26160 0.73490 1.000 0.0230 calc R H22 H Uiso 0.233(4) 0.393(3) 0.977(3) 1.000 0.0330 . . H24A H Uiso 0.54760 0.51810 0.81740 1.000 0.0230 calc R H24B H Uiso 0.39170 0.66960 0.83640 1.000 0.0230 calc R H25A H Uiso 0.32560 0.74540 0.58670 1.000 0.0230 calc R H25B H Uiso 0.49000 0.60050 0.56490 1.000 0.0230 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0177(2) 0.0221(2) 0.0104(2) -0.0035(1) -0.0037(1) -0.0063(1) N1 0.0493(12) 0.0370(11) 0.0213(9) -0.0140(8) -0.0154(8) 0.0167(9) N2 0.0565(13) 0.0328(11) 0.0244(10) -0.0047(8) -0.0159(9) -0.0025(9) N3 0.0364(10) 0.0283(10) 0.0162(8) -0.0059(7) -0.0077(7) -0.0019(8) N11 0.0164(7) 0.0194(8) 0.0138(7) -0.0064(6) -0.0036(6) -0.0035(6) N12 0.0224(8) 0.0266(9) 0.0117(7) -0.0024(7) -0.0051(6) -0.0081(7) N21 0.0163(7) 0.0172(8) 0.0147(7) -0.0050(6) -0.0022(6) -0.0045(6) N22 0.0236(8) 0.0303(10) 0.0119(7) -0.0046(7) -0.0046(6) -0.0102(7) C1 0.0259(10) 0.0232(10) 0.0181(9) -0.0088(8) -0.0029(8) -0.0039(8) C2 0.0211(9) 0.0180(9) 0.0205(10) -0.0053(8) -0.0038(7) -0.0003(7) C13 0.0157(8) 0.0153(9) 0.0135(8) -0.0057(7) -0.0023(6) 0.0009(7) C14 0.0196(9) 0.0203(10) 0.0183(9) -0.0054(7) -0.0026(7) -0.0054(7) C15 0.0197(9) 0.0209(10) 0.0173(9) -0.0063(7) -0.0033(7) -0.0065(7) C23 0.0154(8) 0.0162(9) 0.0151(8) -0.0068(7) -0.0031(6) 0.0000(7) C24 0.0184(9) 0.0239(10) 0.0181(9) -0.0091(8) -0.0050(7) -0.0038(7) C25 0.0196(9) 0.0231(10) 0.0176(9) -0.0077(8) -0.0034(7) -0.0069(8) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.6050(19) . . yes Cu1 N11 1.9983(15) . . yes Cu1 N21 2.0023(15) . . yes N1 C1 1.316(3) . . yes N1 C2 1.306(2) . . yes N2 C1 1.147(3) . . yes N3 C2 1.154(2) . . yes N11 C13 1.297(2) . . yes N11 C15 1.482(2) . . yes N12 C13 1.326(2) . . yes N12 C14 1.471(2) . . yes N21 C23 1.292(2) . . yes N21 C25 1.486(2) . . yes N22 C23 1.330(2) . . yes N22 C24 1.468(2) . . yes N12 H12 0.76(3) . . no N22 H22 0.77(3) . . no C13 C23 1.483(3) . . no C14 C15 1.547(2) . . no C24 C25 1.550(2) . . no C14 H14A 0.9898 . . no C14 H14B 0.9898 . . no C15 H15A 0.9905 . . no C15 H15B 0.9904 . . no C24 H24A 0.9900 . . no C24 H24B 0.9902 . . no C25 H25A 0.9903 . . no C25 H25B 0.9904 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N11 83.50(6) . . . yes N1 Cu1 N21 96.76(6) . . . yes N1 Cu1 N1 180.00 . . 2_566 yes N1 Cu1 N11 96.50(6) . . 2_566 yes N1 Cu1 N21 83.24(6) . . 2_566 yes N11 Cu1 N21 81.28(6) . . . yes N1 Cu1 N11 96.50(6) 2_566 . . yes N11 Cu1 N11 180.00 . . 2_566 yes N11 Cu1 N21 98.72(6) . . 2_566 yes N1 Cu1 N21 83.24(6) 2_566 . . yes N11 Cu1 N21 98.72(6) 2_566 . . yes N21 Cu1 N21 180.00 . . 2_566 yes N1 Cu1 N11 83.50(6) 2_566 . 2_566 yes N1 Cu1 N21 96.76(6) 2_566 . 2_566 yes N11 Cu1 N21 81.28(6) 2_566 . 2_566 yes Cu1 N1 C1 120.17(15) . . . yes Cu1 N1 C2 116.54(13) . . . yes C1 N1 C2 123.29(19) . . . yes Cu1 N11 C13 113.72(12) . . . yes Cu1 N11 C15 138.14(12) . . . yes C13 N11 C15 106.72(15) . . . yes C13 N12 C14 108.56(15) . . . yes Cu1 N21 C23 113.39(12) . . . yes Cu1 N21 C25 138.32(12) . . . yes C23 N21 C25 106.98(15) . . . yes C23 N22 C24 108.66(15) . . . yes C14 N12 H12 126(2) . . . no C13 N12 H12 125(2) . . . no C23 N22 H22 124(2) . . . no C24 N22 H22 127(2) . . . no N1 C1 N2 171.3(3) . . . yes N1 C2 N3 171.1(2) . . . yes N11 C13 C23 115.22(15) . . . yes N12 C13 C23 127.68(16) . . . yes N11 C13 N12 117.08(17) . . . yes N12 C14 C15 101.78(14) . . . yes N11 C15 C14 104.66(15) . . . yes N21 C23 N22 117.32(17) . . . yes N22 C23 C13 126.74(16) . . . yes N21 C23 C13 115.92(16) . . . yes N22 C24 C25 102.16(15) . . . yes N21 C25 C24 104.77(14) . . . yes N12 C14 H14A 111.42 . . . no N12 C14 H14B 111.37 . . . no C15 C14 H14A 111.42 . . . no C15 C14 H14B 111.42 . . . no H14A C14 H14B 109.29 . . . no N11 C15 H15A 110.86 . . . no N11 C15 H15B 110.85 . . . no C14 C15 H15A 110.81 . . . no C14 C15 H15B 110.79 . . . no H15A C15 H15B 108.85 . . . no N22 C24 H24A 111.34 . . . no N22 C24 H24B 111.32 . . . no C25 C24 H24A 111.36 . . . no C25 C24 H24B 111.33 . . . no H24A C24 H24B 109.20 . . . no N21 C25 H25A 110.79 . . . no N21 C25 H25B 110.75 . . . no C24 C25 H25A 110.80 . . . no C24 C25 H25B 110.82 . . . no H25A C25 H25B 108.88 . . . no 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 N11 Cu1 N1 C1 -46.68(16) . . . . no N11 Cu1 N1 C2 134.10(16) . . . . no N21 Cu1 N1 C1 33.70(17) . . . . no N21 Cu1 N1 C2 -145.52(15) . . . . no N11 Cu1 N1 C1 133.32(16) 2_566 . . . no N11 Cu1 N1 C2 -45.90(16) 2_566 . . . no N21 Cu1 N1 C1 -146.30(17) 2_566 . . . no N21 Cu1 N1 C2 34.48(15) 2_566 . . . no N1 Cu1 N11 C13 96.26(14) . . . . no N1 Cu1 N11 C15 -67.74(18) . . . . no N21 Cu1 N11 C13 -1.63(14) . . . . no N21 Cu1 N11 C15 -165.63(19) . . . . no N1 Cu1 N11 C13 -83.74(14) 2_566 . . . no N1 Cu1 N11 C15 112.26(18) 2_566 . . . no N21 Cu1 N11 C13 178.37(14) 2_566 . . . no N21 Cu1 N11 C15 14.37(19) 2_566 . . . no N1 Cu1 N21 C23 -85.14(14) . . . . no N1 Cu1 N21 C25 110.24(18) . . . . no N11 Cu1 N21 C23 -2.82(14) . . . . no N11 Cu1 N21 C25 -167.43(19) . . . . no N1 Cu1 N21 C23 94.86(14) 2_566 . . . no N1 Cu1 N21 C25 -69.76(18) 2_566 . . . no N11 Cu1 N21 C23 177.18(14) 2_566 . . . no N11 Cu1 N21 C25 12.57(19) 2_566 . . . no Cu1 N11 C13 N12 -173.33(14) . . . . no Cu1 N11 C13 C23 5.3(2) . . . . no C15 N11 C13 N12 -4.4(2) . . . . no C15 N11 C13 C23 174.23(15) . . . . no Cu1 N11 C15 C14 174.17(14) . . . . no C13 N11 C15 C14 9.45(19) . . . . no C14 N12 C13 N11 -3.1(2) . . . . no C14 N12 C13 C23 178.50(18) . . . . no C13 N12 C14 C15 8.56(19) . . . . no Cu1 N21 C23 N22 -172.02(14) . . . . no Cu1 N21 C23 C13 6.3(2) . . . . no C25 N21 C23 N22 -2.7(2) . . . . no C25 N21 C23 C13 175.72(16) . . . . no Cu1 N21 C25 C24 168.53(14) . . . . no C23 N21 C25 C24 3.28(19) . . . . no C24 N22 C23 N21 0.7(2) . . . . no C24 N22 C23 C13 -177.44(18) . . . . no C23 N22 C24 C25 1.43(19) . . . . no N11 C13 C23 N21 -8.0(3) . . . . no N11 C13 C23 N22 170.23(19) . . . . no N12 C13 C23 N21 170.50(19) . . . . no N12 C13 C23 N22 -11.3(3) . . . . no N12 C14 C15 N11 -10.61(18) . . . . no N22 C24 C25 N21 -2.77(18) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cu1 N12 4.0436(17) . . no Cu1 N22 4.0437(17) . . no Cu1 N12 4.0436(17) . 2_566 no Cu1 N22 4.0437(17) . 2_566 no Cu1 H25B 3.4101 . 1_455 no Cu1 H25B 3.4101 . 2_666 no N1 C25 3.377(3) . 2_666 no N2 N12 3.179(2) . 2_557 no N2 C14 3.136(2) . 2_557 no N3 C23 3.413(3) . 2_566 no N3 N12 3.074(2) . 1_554 no N3 N22 2.869(2) . 1_554 no N12 N22 3.097(2) . . no N12 N2 3.179(2) . 2_557 no N12 N3 3.074(2) . 1_556 no N12 Cu1 4.0436(17) . . no N22 Cu1 4.0437(17) . . no N22 N12 3.097(2) . . no N22 N3 2.869(2) . 1_556 no N1 H25B 2.8039 . 2_666 no N2 H24B 2.7298 . 1_545 no N2 H12 2.76(3) . 2_557 no N2 H25A 2.7642 . 1_545 no N2 H14A 2.8644 . 2_557 no N3 H22 2.12(3) . 1_554 no N3 H12 2.36(3) . 1_554 no N3 H15A 2.7491 . 2_556 no N11 H24A 2.7728 . 1_455 no N12 H22 2.94(3) . . no N12 H24B 2.9061 . 2_567 no N21 H25B 2.9425 . 2_666 no C1 C13 3.580(3) . . no C1 C25 3.502(3) . 2_666 no C2 C24 3.399(3) . 2_666 no C2 C23 3.408(3) . 2_566 no C13 C1 3.580(3) . . no C14 N2 3.136(2) . 2_557 no C14 C14 3.434(3) . 2_457 no C15 C24 3.598(3) . 1_455 no C15 C25 3.463(3) . 2_566 no C23 C2 3.408(3) . 2_566 no C23 N3 3.413(3) . 2_566 no C24 C15 3.598(3) . 1_655 no C24 C2 3.399(3) . 2_666 no C25 N1 3.377(3) . 2_666 no C25 C15 3.463(3) . 2_566 no C25 C1 3.502(3) . 2_666 no C1 H25A 2.9918 . 1_545 no C1 H25B 2.9935 . 2_666 no C2 H24A 2.9611 . 2_666 no C2 H15A 2.9671 . 2_556 no C2 H22 3.06(3) . 1_554 no C13 H24A 3.0771 . 1_455 no C14 H14B 2.9978 . 2_457 no C14 H14A 3.0901 . 2_457 no C15 H24A 2.9287 . 1_455 no C23 H15B 3.0809 . 1_655 no C24 H15B 2.9795 . 1_655 no C25 H15B 3.0816 . 1_655 no C25 H25B 3.0800 . 2_666 no H12 N3 2.36(3) . 1_556 no H12 N2 2.76(3) . 2_557 no H14A N2 2.8644 . 2_557 no H14A C14 3.0901 . 2_457 no H14A H14B 2.4694 . 2_457 no H14A H24B 2.4830 . 2_567 no H14B C14 2.9978 . 2_457 no H14B H14A 2.4694 . 2_457 no H15A N3 2.7491 . 2_556 no H15A C2 2.9671 . 2_556 no H15B C23 3.0809 . 1_455 no H15B C24 2.9795 . 1_455 no H15B C25 3.0816 . 1_455 no H15B H24A 2.5421 . 1_455 no H22 N3 2.12(3) . 1_556 no H22 N12 2.94(3) . . no H22 C2 3.06(3) . 1_556 no H24A N11 2.7728 . 1_655 no H24A C13 3.0771 . 1_655 no H24A C15 2.9287 . 1_655 no H24A H15B 2.5421 . 1_655 no H24A C2 2.9611 . 2_666 no H24B N2 2.7298 . 1_565 no H24B N12 2.9061 . 2_567 no H24B H14A 2.4830 . 2_567 no H25A N2 2.7642 . 1_565 no H25A C1 2.9918 . 1_565 no H25B Cu1 3.4101 . 1_655 no H25B Cu1 3.4101 . 2_666 no H25B N1 2.8039 . 2_666 no H25B N21 2.9425 . 2_666 no H25B C1 2.9935 . 2_666 no H25B C25 3.0800 . 2_666 no H25B H25B 2.4087 . 2_666 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N12 H12 N3 0.76(3) 2.36(3) 3.074(2) 157(2) 1_556 yes N22 H22 N3 0.77(3) 2.12(3) 2.869(2) 167(3) 1_556 yes #===END #============================================================================== #============================================================================== data_3 _database_code_CSD 206280 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(Co 2+), 2(C6 H10 N4), 2(C2 N3 1-)' _chemical_formula_structural ? _chemical_formula_sum 'C16 H20 Co N14' _chemical_formula_iupac ? _chemical_formula_weight 467.39 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 6.7844(10) _cell_length_b 8.097(2) _cell_length_c 9.462(2) _cell_angle_alpha 67.890(8) _cell_angle_beta 82.440(9) _cell_angle_gamma 86.531(10) _cell_volume 477.34(17) _cell_formula_units_Z 1 _cell_measurement_temperature 150 _cell_measurement_reflns_used 130 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _cell_special_details ; Quoted _cell_measurement_* data items refer to the initial cell determination. The cell parameters as reported in _cell_* are based on the complete data set. ; _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 241 _exptl_absorpt_coefficient_mu 0.939 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Enraf-Nonius CAD4 Turbo Nonius Kappa CCD area detector ; _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 11643 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 2182 _reflns_number_gt 2049 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'Denzo (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'PLATON (Spek, 2002)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2 > 2sigma(F^2) is used only for calculating -R-factor-obs 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 'w=1/[\s^2^(F~o~^2^)+(0.0119P)^2^+0.28P] where P=(F~o~^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct ' _atom_sites_solution_secondary 'difmap ' _atom_sites_solution_hydrogens 'difmap ' _refine_ls_hydrogen_treatment 'mixed ' _refine_ls_extinction_method 'none ' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack none _refine_ls_number_reflns 2182 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0267 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0581 _refine_ls_wR_factor_gt 0.0571 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.298 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.049 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Co1 Co Uani 0.00000 0.50000 0.00000 1.000 0.0136(1) . . N1 N Uani 0.13811(18) 0.25594(15) -0.02906(13) 1.000 0.0181(3) . . N2 N Uani 0.2850(2) 0.02773(18) 0.19077(16) 1.000 0.0308(4) . . N3 N Uani 0.1324(2) 0.23228(17) -0.28162(14) 1.000 0.0239(4) . . N11 N Uani -0.13425(16) 0.32969(15) 0.21488(12) 1.000 0.0143(3) . . N12 N Uani -0.10632(18) 0.19534(16) 0.46702(14) 1.000 0.0197(3) . . N21 N Uani 0.20218(16) 0.50793(15) 0.14820(12) 1.000 0.0141(3) . . N22 N Uani 0.25375(19) 0.43566(18) 0.39389(15) 1.000 0.0226(4) . . C1 C Uani 0.2186(2) 0.12885(18) 0.08500(16) 1.000 0.0185(4) . . C2 C Uani 0.1395(2) 0.23496(17) -0.16078(15) 1.000 0.0165(4) . . C13 C Uani -0.03665(19) 0.31226(17) 0.32870(15) 1.000 0.0137(3) . . C14 C Uani -0.2904(2) 0.11986(19) 0.45242(16) 1.000 0.0181(4) . . C15 C Uani -0.2944(2) 0.19587(18) 0.27616(15) 1.000 0.0169(4) . . C23 C Uani 0.14523(19) 0.41968(17) 0.29188(15) 1.000 0.0138(3) . . C24 C Uani 0.4110(2) 0.56554(19) 0.31134(16) 1.000 0.0185(4) . . C25 C Uani 0.3763(2) 0.61324(19) 0.14195(16) 1.000 0.0185(4) . . H12 H Uiso -0.063(3) 0.184(2) 0.551(2) 1.000 0.0240 . . H14A H Uiso -0.40780 0.16040 0.50540 1.000 0.0220 calc R H14B H Uiso -0.28480 -0.01210 0.49400 1.000 0.0220 calc R H15A H Uiso -0.26850 0.10040 0.23440 1.000 0.0200 calc R H15B H Uiso -0.42490 0.25230 0.24940 1.000 0.0200 calc R H22 H Uiso 0.230(3) 0.387(2) 0.488(2) 1.000 0.0270 . . H24A H Uiso 0.54460 0.51200 0.33090 1.000 0.0220 calc R H24B H Uiso 0.39530 0.67160 0.34010 1.000 0.0220 calc R H25A H Uiso 0.34880 0.74240 0.09200 1.000 0.0220 calc R H25B H Uiso 0.49450 0.58100 0.08380 1.000 0.0220 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0155(1) 0.0159(1) 0.0092(1) -0.0035(1) -0.0026(1) -0.0025(1) N1 0.0247(6) 0.0183(6) 0.0116(6) -0.0056(5) -0.0049(5) 0.0028(5) N2 0.0429(8) 0.0253(7) 0.0223(7) -0.0045(6) -0.0117(6) 0.0029(6) N3 0.0321(7) 0.0249(7) 0.0148(6) -0.0072(5) -0.0040(5) -0.0003(5) N11 0.0144(5) 0.0160(6) 0.0121(5) -0.0044(4) -0.0020(4) -0.0027(4) N12 0.0211(6) 0.0244(6) 0.0105(6) -0.0011(5) -0.0035(5) -0.0086(5) N21 0.0145(5) 0.0155(5) 0.0118(5) -0.0041(4) -0.0020(4) -0.0030(4) N22 0.0230(6) 0.0323(7) 0.0107(6) -0.0038(5) -0.0034(5) -0.0116(5) C1 0.0216(7) 0.0184(7) 0.0165(7) -0.0072(6) -0.0019(5) -0.0031(5) C2 0.0171(7) 0.0141(6) 0.0160(7) -0.0030(5) -0.0013(5) -0.0007(5) C13 0.0151(6) 0.0136(6) 0.0119(6) -0.0046(5) -0.0012(5) 0.0008(5) C14 0.0171(7) 0.0192(7) 0.0163(7) -0.0038(5) -0.0020(5) -0.0051(5) C15 0.0181(7) 0.0171(7) 0.0157(7) -0.0055(5) -0.0019(5) -0.0049(5) C23 0.0146(6) 0.0147(6) 0.0127(6) -0.0054(5) -0.0031(5) 0.0008(5) C24 0.0175(7) 0.0223(7) 0.0177(7) -0.0089(6) -0.0027(5) -0.0048(5) C25 0.0179(7) 0.0216(7) 0.0158(7) -0.0061(6) -0.0013(5) -0.0068(5) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N1 2.2307(14) . . yes Co1 N11 2.1022(12) . . yes Co1 N21 2.1063(12) . . yes N1 C1 1.3315(19) . . yes N1 C2 1.3185(18) . . yes N2 C1 1.154(2) . . yes N3 C2 1.1591(19) . . yes N11 C13 1.2962(17) . . yes N11 C15 1.4814(19) . . yes N12 C13 1.3384(18) . . yes N12 C14 1.4675(19) . . yes N21 C23 1.2931(17) . . yes N21 C25 1.4804(19) . . yes N22 C23 1.3353(19) . . yes N22 C24 1.467(2) . . yes N12 H12 0.854(18) . . no N22 H22 0.825(17) . . no C13 C23 1.4796(19) . . no C14 C15 1.5486(19) . . no C24 C25 1.548(2) . . no C14 H14A 0.9903 . . no C14 H14B 0.9902 . . no C15 H15A 0.9898 . . no C15 H15B 0.9898 . . no C24 H24A 0.9899 . . no C24 H24B 0.9900 . . no C25 H25A 0.9897 . . no C25 H25B 0.9903 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co1 N11 86.85(5) . . . yes N1 Co1 N21 93.83(5) . . . yes N1 Co1 N1 180.00 . . 2_565 yes N1 Co1 N11 93.15(5) . . 2_565 yes N1 Co1 N21 86.17(5) . . 2_565 yes N11 Co1 N21 78.07(4) . . . yes N1 Co1 N11 93.15(5) 2_565 . . yes N11 Co1 N11 180.00 . . 2_565 yes N11 Co1 N21 101.93(4) . . 2_565 yes N1 Co1 N21 86.17(5) 2_565 . . yes N11 Co1 N21 101.93(4) 2_565 . . yes N21 Co1 N21 180.00 . . 2_565 yes N1 Co1 N11 86.85(5) 2_565 . 2_565 yes N1 Co1 N21 93.83(5) 2_565 . 2_565 yes N11 Co1 N21 78.07(4) 2_565 . 2_565 yes Co1 N1 C1 121.27(10) . . . yes Co1 N1 C2 119.92(10) . . . yes C1 N1 C2 118.80(13) . . . yes Co1 N11 C13 114.15(9) . . . yes Co1 N11 C15 138.24(9) . . . yes C13 N11 C15 106.63(11) . . . yes C13 N12 C14 108.36(11) . . . yes Co1 N21 C23 113.81(9) . . . yes Co1 N21 C25 138.17(9) . . . yes C23 N21 C25 106.72(11) . . . yes C23 N22 C24 108.66(12) . . . yes C14 N12 H12 126.1(13) . . . no C13 N12 H12 124.4(13) . . . no C23 N22 H22 125.4(14) . . . no C24 N22 H22 125.8(14) . . . no N1 C1 N2 174.30(17) . . . yes N1 C2 N3 173.55(16) . . . yes N11 C13 C23 116.61(12) . . . yes N12 C13 C23 126.27(12) . . . yes N11 C13 N12 117.09(12) . . . yes N12 C14 C15 101.90(11) . . . yes N11 C15 C14 104.96(11) . . . yes N21 C23 N22 117.22(13) . . . yes N22 C23 C13 125.78(12) . . . yes N21 C23 C13 116.99(12) . . . yes N22 C24 C25 101.90(11) . . . yes N21 C25 C24 105.41(11) . . . yes N12 C14 H14A 111.36 . . . no N12 C14 H14B 111.40 . . . no C15 C14 H14A 111.40 . . . no C15 C14 H14B 111.40 . . . no H14A C14 H14B 109.25 . . . no N11 C15 H15A 110.74 . . . no N11 C15 H15B 110.76 . . . no C14 C15 H15A 110.74 . . . no C14 C15 H15B 110.77 . . . no H15A C15 H15B 108.85 . . . no N22 C24 H24A 111.39 . . . no N22 C24 H24B 111.40 . . . no C25 C24 H24A 111.38 . . . no C25 C24 H24B 111.38 . . . no H24A C24 H24B 109.26 . . . no N21 C25 H25A 110.68 . . . no N21 C25 H25B 110.67 . . . no C24 C25 H25A 110.66 . . . no C24 C25 H25B 110.63 . . . no H25A C25 H25B 108.77 . . . no 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 N11 Co1 N1 C1 -44.07(11) . . . . no N11 Co1 N1 C2 135.37(11) . . . . no N21 Co1 N1 C1 33.74(11) . . . . no N21 Co1 N1 C2 -146.83(11) . . . . no N11 Co1 N1 C1 135.93(11) 2_565 . . . no N11 Co1 N1 C2 -44.63(11) 2_565 . . . no N21 Co1 N1 C1 -146.26(11) 2_565 . . . no N21 Co1 N1 C2 33.17(11) 2_565 . . . no N1 Co1 N11 C13 94.93(11) . . . . no N1 Co1 N11 C15 -71.74(14) . . . . no N21 Co1 N11 C13 0.34(10) . . . . no N21 Co1 N11 C15 -166.33(15) . . . . no N1 Co1 N11 C13 -85.07(11) 2_565 . . . no N1 Co1 N11 C15 108.26(14) 2_565 . . . no N21 Co1 N11 C13 -179.66(10) 2_565 . . . no N21 Co1 N11 C15 13.67(15) 2_565 . . . no N1 Co1 N21 C23 -89.91(11) . . . . no N1 Co1 N21 C25 105.43(14) . . . . no N11 Co1 N21 C23 -3.95(10) . . . . no N11 Co1 N21 C25 -168.61(15) . . . . no N1 Co1 N21 C23 90.09(11) 2_565 . . . no N1 Co1 N21 C25 -74.57(14) 2_565 . . . no N11 Co1 N21 C23 176.05(10) 2_565 . . . no N11 Co1 N21 C25 11.39(15) 2_565 . . . no Co1 N11 C13 N12 -175.14(10) . . . . no Co1 N11 C13 C23 2.92(16) . . . . no C15 N11 C13 N12 -4.36(18) . . . . no C15 N11 C13 C23 173.70(12) . . . . no Co1 N11 C15 C14 176.27(11) . . . . no C13 N11 C15 C14 8.95(15) . . . . no C14 N12 C13 N11 -2.59(18) . . . . no C14 N12 C13 C23 179.56(14) . . . . no C13 N12 C14 C15 7.82(16) . . . . no Co1 N21 C23 N22 -172.30(11) . . . . no Co1 N21 C23 C13 6.68(16) . . . . no C25 N21 C23 N22 -2.92(18) . . . . no C25 N21 C23 C13 176.06(12) . . . . no Co1 N21 C25 C24 166.31(11) . . . . no C23 N21 C25 C24 0.95(15) . . . . no C24 N22 C23 N21 3.69(19) . . . . no C24 N22 C23 C13 -175.20(14) . . . . no C23 N22 C24 C25 -2.57(16) . . . . no N11 C13 C23 N21 -6.6(2) . . . . no N11 C13 C23 N22 172.26(15) . . . . no N12 C13 C23 N21 171.23(14) . . . . no N12 C13 C23 N22 -9.9(2) . . . . no N12 C14 C15 N11 -9.93(14) . . . . no N22 C24 C25 N21 0.98(15) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag N1 C25 3.429(2) . 2_665 no N2 N12 3.170(2) . 2_556 no N2 C14 3.133(2) . 2_556 no N3 N22 2.9171(19) . 1_554 no N3 N12 3.159(2) . 1_554 no N3 C23 3.271(2) . 2_565 no N12 N3 3.159(2) . 1_556 no N12 N12 3.267(2) . 2_556 no N12 N22 3.058(2) . . no N12 N2 3.170(2) . 2_556 no N22 N12 3.058(2) . . no N22 N3 2.9171(19) . 1_556 no N1 H25B 2.7871 . 2_665 no N2 H24B 2.7967 . 1_545 no N2 H12 2.714(18) . 2_556 no N2 H14A 2.9085 . 2_556 no N2 H25A 2.7922 . 1_545 no N2 H14B 2.9372 . 2_556 no N3 H22 2.103(18) . 1_554 no N3 H12 2.345(19) . 1_554 no N3 H15A 2.6851 . 2_555 no N11 H24A 2.8866 . 1_455 no N12 H22 2.90(2) . . no N12 H24B 2.9357 . 2_566 no N22 H12 2.896(19) . . no C1 C13 3.426(2) . . no C1 C23 3.563(2) . . no C1 C25 3.506(2) . 2_665 no C2 C23 3.234(2) . 2_565 no C2 C24 3.415(2) . 2_665 no C2 C13 3.471(2) . 2_565 no C13 C1 3.426(2) . . no C13 C2 3.471(2) . 2_565 no C14 N2 3.133(2) . 2_556 no C14 C14 3.368(2) . 2_456 no C15 C24 3.594(2) . 1_455 no C23 C1 3.563(2) . . no C23 C2 3.234(2) . 2_565 no C23 N3 3.271(2) . 2_565 no C24 C2 3.415(2) . 2_665 no C24 C15 3.594(2) . 1_655 no C25 C1 3.506(2) . 2_665 no C25 N1 3.429(2) . 2_665 no C1 H25B 2.9614 . 2_665 no C2 H15A 3.0985 . 2_555 no C2 H24A 2.9194 . 2_665 no C2 H22 3.068(18) . 1_554 no C14 H24B 3.0322 . 2_566 no C14 H14B 2.9852 . 2_456 no C14 H14A 3.0277 . 2_456 no C15 H24A 2.9196 . 1_455 no C24 H15B 2.9362 . 1_655 no C25 H15B 3.0068 . 1_655 no H12 N3 2.345(19) . 1_556 no H12 N22 2.896(19) . . no H12 H22 2.52(3) . . no H12 N2 2.714(18) . 2_556 no H14A N2 2.9085 . 2_556 no H14A C14 3.0277 . 2_456 no H14A H14B 2.4670 . 2_456 no H14A H24B 2.3533 . 2_566 no H14B N2 2.9372 . 2_556 no H14B C14 2.9852 . 2_456 no H14B H14A 2.4670 . 2_456 no H15A N3 2.6851 . 2_555 no H15A C2 3.0985 . 2_555 no H15B C24 2.9362 . 1_455 no H15B C25 3.0068 . 1_455 no H15B H24A 2.4870 . 1_455 no H15B H25B 2.5976 . 1_455 no H22 N3 2.103(18) . 1_556 no H22 N12 2.90(2) . . no H22 C2 3.068(18) . 1_556 no H22 H12 2.52(3) . . no H24A N11 2.8866 . 1_655 no H24A C15 2.9196 . 1_655 no H24A H15B 2.4870 . 1_655 no H24A C2 2.9194 . 2_665 no H24B N2 2.7967 . 1_565 no H24B N12 2.9357 . 2_566 no H24B C14 3.0322 . 2_566 no H24B H14A 2.3533 . 2_566 no H25A N2 2.7922 . 1_565 no H25B H15B 2.5976 . 1_655 no H25B N1 2.7871 . 2_665 no H25B C1 2.9614 . 2_665 no H25B H25B 2.4008 . 2_665 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N12 H12 N3 0.854(18) 2.345(19) 3.159(2) 159.3(16) 1_556 yes N22 H22 N3 0.825(17) 2.103(18) 2.9171(19) 169.0(19) 1_556 yes #===END # CIF-file generated for shelxl #============================================================================== #============================================================================== data_4 _database_code_CSD 206281 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(Ni 2+), (C6 H10 N4), 2(C2 N3 1-)' _chemical_formula_structural ? _chemical_formula_sum 'C16 H20 N14 Ni' _chemical_formula_iupac ? _chemical_formula_weight 467.15 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Ni Ni 0.3393 1.1124 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z -x,-y,-z 1/2+x,y,1/2-z 1/2-x,1/2+y,z x,1/2-y,1/2+z _cell_length_a 16.4081(16) _cell_length_b 6.7991(8) _cell_length_c 17.965(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2004.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 401 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _cell_special_details ; Quoted _cell_measurement_* data items refer to the initial cell determination. The cell parameters as reported in _cell_* are based on the complete data set. ; _exptl_crystal_description plate _exptl_crystal_colour grey _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.060 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.006 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD area detector' _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 38769 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 2297 _reflns_number_gt 1811 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'Denzo (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'PLATON (Spek, 2002)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2 > 2sigma(F^2) is used only for calculating -R-factor-obs 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 'w=1/[\s^2^(F~o~^2^)+(0.0407P)^2^+0.64P] where P=(F~o~^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct ' _atom_sites_solution_secondary 'difmap ' _atom_sites_solution_hydrogens difmap # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # (mixed) SHELXL _refine_ls_hydrogen_treatment 'mixed ' _refine_ls_extinction_method 'none ' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack none _refine_ls_number_reflns 2297 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.334 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.051 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Ni1 Ni Uani 0.00000 0.00000 0.00000 1.000 0.0193(1) . . N1 N Uani 0.21713(10) 0.3064(2) -0.10445(9) 1.000 0.0444(5) . . N2 N Uani 0.09932(9) 0.1307(2) -0.05404(7) 1.000 0.0291(4) . . N3 N Uani 0.28899(11) 0.2517(2) -0.22177(9) 1.000 0.0455(5) . . N11 N Uani 0.07809(8) -0.21783(18) 0.03594(7) 1.000 0.0241(4) . . N12 N Uani 0.16779(10) -0.3108(2) 0.12286(8) 1.000 0.0372(5) . . N21 N Uani 0.03648(8) 0.11408(18) 0.10378(6) 1.000 0.0232(4) . . N22 N Uani 0.09947(10) 0.0386(2) 0.21113(8) 1.000 0.0328(4) . . C1 C Uani 0.15458(10) 0.2046(2) -0.08144(8) 1.000 0.0262(4) . . C2 C Uani 0.25255(10) 0.2695(2) -0.16759(10) 1.000 0.0301(5) . . C13 C Uani 0.11024(9) -0.1845(2) 0.09973(8) 1.000 0.0220(4) . . C14 C Uani 0.18045(10) -0.4578(2) 0.06441(9) 1.000 0.0312(5) . . C15 C Uani 0.11716(11) -0.3956(2) 0.00540(9) 1.000 0.0293(5) . . C23 C Uani 0.08285(9) -0.0055(2) 0.13964(9) 1.000 0.0219(4) . . C24 C Uani 0.06692(11) 0.2359(2) 0.22591(10) 1.000 0.0350(5) . . C25 C Uani 0.01125(10) 0.2674(2) 0.15755(9) 1.000 0.0286(5) . . H12 H Uiso 0.1899(12) -0.309(3) 0.1660(12) 1.000 0.0450 . . H14A H Uiso 0.16960 -0.59240 0.08300 1.000 0.0370 calc R H14B H Uiso 0.23660 -0.45160 0.04430 1.000 0.0370 calc R H15A H Uiso 0.14410 -0.36630 -0.04260 1.000 0.0350 calc R H15B H Uiso 0.07650 -0.50110 -0.00250 1.000 0.0350 calc R H22 H Uiso 0.1369(13) -0.019(3) 0.2373(11) 1.000 0.0390 . . H24A H Uiso 0.11090 0.33550 0.22800 1.000 0.0420 calc R H24B H Uiso 0.03550 0.23950 0.27290 1.000 0.0420 calc R H25A H Uiso -0.04680 0.25140 0.17130 1.000 0.0340 calc R H25B H Uiso 0.01920 0.40040 0.13630 1.000 0.0340 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0229(2) 0.0192(2) 0.0159(2) -0.0020(1) 0.0007(1) 0.0034(1) N1 0.0496(10) 0.0373(8) 0.0464(9) -0.0162(7) 0.0261(8) -0.0156(8) N2 0.0323(7) 0.0293(7) 0.0258(7) -0.0029(6) 0.0058(6) 0.0000(6) N3 0.0522(10) 0.0436(9) 0.0406(9) 0.0037(7) 0.0198(8) 0.0083(8) N11 0.0275(7) 0.0221(6) 0.0226(7) -0.0034(5) 0.0007(5) 0.0060(5) N12 0.0472(9) 0.0334(8) 0.0311(8) -0.0052(6) -0.0125(7) 0.0168(7) N21 0.0286(7) 0.0215(6) 0.0196(6) -0.0036(5) 0.0005(5) 0.0030(5) N22 0.0446(9) 0.0301(7) 0.0238(7) -0.0048(6) -0.0101(6) 0.0101(6) C1 0.0334(9) 0.0230(7) 0.0223(7) -0.0059(6) 0.0037(7) 0.0041(7) C2 0.0309(8) 0.0247(8) 0.0347(9) 0.0023(7) 0.0075(8) 0.0028(7) C13 0.0228(7) 0.0215(7) 0.0217(7) 0.0022(6) 0.0017(6) 0.0006(6) C14 0.0319(9) 0.0271(8) 0.0347(9) -0.0020(7) 0.0009(7) 0.0074(7) C15 0.0328(9) 0.0248(8) 0.0304(9) -0.0055(7) 0.0014(7) 0.0087(7) C23 0.0238(7) 0.0213(7) 0.0205(7) -0.0007(6) 0.0014(6) -0.0021(6) C24 0.0481(11) 0.0319(9) 0.0249(8) -0.0092(7) -0.0047(8) 0.0088(8) C25 0.0351(9) 0.0267(8) 0.0241(8) -0.0069(7) 0.0007(7) 0.0060(7) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N2 2.0947(14) . . yes Ni1 N11 2.0621(13) . . yes Ni1 N21 2.1062(11) . . yes N1 C1 1.305(2) . . yes N1 C2 1.299(2) . . yes N2 C1 1.148(2) . . yes N3 C2 1.149(2) . . yes N11 C13 1.2818(19) . . yes N11 C15 1.474(2) . . yes N12 C13 1.342(2) . . yes N12 C14 1.464(2) . . yes N21 C23 1.2864(19) . . yes N21 C25 1.4803(19) . . yes N22 C23 1.347(2) . . yes N22 C24 1.468(2) . . yes N12 H12 0.86(2) . . no N22 H22 0.87(2) . . no C13 C23 1.482(2) . . no C14 C15 1.543(2) . . no C24 C25 1.545(2) . . no C14 H14A 0.9903 . . no C14 H14B 0.9905 . . no C15 H15A 0.9893 . . no C15 H15B 0.9898 . . no C24 H24A 0.9903 . . no C24 H24B 0.9895 . . no C25 H25A 0.9900 . . no C25 H25B 0.9902 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni1 N11 88.07(5) . . . yes N2 Ni1 N21 91.89(5) . . . yes N2 Ni1 N2 180.00 . . 5_555 yes N2 Ni1 N11 91.93(5) . . 5_555 yes N2 Ni1 N21 88.11(5) . . 5_555 yes N11 Ni1 N21 79.09(5) . . . yes N2 Ni1 N11 91.93(5) 5_555 . . yes N11 Ni1 N11 180.00 . . 5_555 yes N11 Ni1 N21 100.91(5) . . 5_555 yes N2 Ni1 N21 88.11(5) 5_555 . . yes N11 Ni1 N21 100.91(5) 5_555 . . yes N21 Ni1 N21 180.00 . . 5_555 yes N2 Ni1 N11 88.07(5) 5_555 . 5_555 yes N2 Ni1 N21 91.89(5) 5_555 . 5_555 yes N11 Ni1 N21 79.09(5) 5_555 . 5_555 yes C1 N1 C2 121.73(15) . . . yes Ni1 N2 C1 177.76(12) . . . yes Ni1 N11 C13 114.12(10) . . . yes Ni1 N11 C15 137.95(10) . . . yes C13 N11 C15 107.38(12) . . . yes C13 N12 C14 108.33(13) . . . yes Ni1 N21 C23 112.25(10) . . . yes Ni1 N21 C25 139.25(10) . . . yes C23 N21 C25 106.48(12) . . . yes C23 N22 C24 107.59(13) . . . yes C14 N12 H12 126.8(14) . . . no C13 N12 H12 124.7(14) . . . no C23 N22 H22 124.1(13) . . . no C24 N22 H22 124.9(13) . . . no N1 C1 N2 171.66(16) . . . yes N1 C2 N3 173.28(17) . . . yes N11 C13 C23 116.93(13) . . . yes N12 C13 C23 126.07(13) . . . yes N11 C13 N12 116.95(13) . . . yes N12 C14 C15 102.13(12) . . . yes N11 C15 C14 105.17(12) . . . yes N21 C23 N22 117.17(13) . . . yes N22 C23 C13 125.64(13) . . . yes N21 C23 C13 117.13(14) . . . yes N22 C24 C25 101.42(13) . . . yes N21 C25 C24 104.81(12) . . . yes N12 C14 H14A 111.31 . . . no N12 C14 H14B 111.37 . . . no C15 C14 H14A 111.34 . . . no C15 C14 H14B 111.33 . . . no H14A C14 H14B 109.24 . . . no N11 C15 H15A 110.71 . . . no N11 C15 H15B 110.76 . . . no C14 C15 H15A 110.69 . . . no C14 C15 H15B 110.70 . . . no H15A C15 H15B 108.79 . . . no N22 C24 H24A 111.51 . . . no N22 C24 H24B 111.50 . . . no C25 C24 H24A 111.47 . . . no C25 C24 H24B 111.51 . . . no H24A C24 H24B 109.29 . . . no N21 C25 H25A 110.76 . . . no N21 C25 H25B 110.77 . . . no C24 C25 H25A 110.80 . . . no C24 C25 H25B 110.80 . . . no H25A C25 H25B 108.86 . . . no 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 N11 C13 92.07(11) . . . . no N2 Ni1 N11 C15 -78.10(15) . . . . no N21 Ni1 N11 C13 -0.23(11) . . . . no N21 Ni1 N11 C15 -170.39(16) . . . . no N2 Ni1 N11 C13 -87.93(11) 5_555 . . . no N2 Ni1 N11 C15 101.90(15) 5_555 . . . no N21 Ni1 N11 C13 179.77(11) 5_555 . . . no N21 Ni1 N11 C15 9.61(16) 5_555 . . . no N2 Ni1 N21 C23 -91.71(11) . . . . no N2 Ni1 N21 C25 107.51(15) . . . . no N11 Ni1 N21 C23 -4.04(11) . . . . no N11 Ni1 N21 C25 -164.81(15) . . . . no N2 Ni1 N21 C23 88.29(11) 5_555 . . . no N2 Ni1 N21 C25 -72.49(15) 5_555 . . . no N11 Ni1 N21 C23 175.96(11) 5_555 . . . no N11 Ni1 N21 C25 15.19(15) 5_555 . . . no Ni1 N11 C13 N12 -173.49(11) . . . . no Ni1 N11 C13 C23 4.04(17) . . . . no C15 N11 C13 N12 -0.38(18) . . . . no C15 N11 C13 C23 177.15(13) . . . . no Ni1 N11 C15 C14 169.61(11) . . . . no C13 N11 C15 C14 -0.99(16) . . . . no C14 N12 C13 N11 1.66(19) . . . . no C14 N12 C13 C23 -175.61(14) . . . . no C13 N12 C14 C15 -2.04(16) . . . . no Ni1 N21 C23 N22 -169.96(11) . . . . no Ni1 N21 C23 C13 7.31(16) . . . . no C25 N21 C23 N22 -2.92(18) . . . . no C25 N21 C23 C13 174.36(12) . . . . no Ni1 N21 C25 C24 173.22(11) . . . . no C23 N21 C25 C24 11.75(16) . . . . no C24 N22 C23 N21 -7.9(2) . . . . no C24 N22 C23 C13 175.13(14) . . . . no C23 N22 C24 C25 14.04(17) . . . . no N11 C13 C23 N21 -7.9(2) . . . . no N11 C13 C23 N22 169.07(15) . . . . no N12 C13 C23 N21 169.33(15) . . . . no N12 C13 C23 N22 -13.7(2) . . . . no N12 C14 C15 N11 1.80(15) . . . . no N22 C24 C25 N21 -15.34(15) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Ni1 H15B 3.6171 . 1_565 no Ni1 H15B 3.6171 . 5_545 no N1 C15 3.270(2) . 1_565 no N1 C2 3.384(2) . 7_555 no N2 C15 3.406(2) . 1_565 no N3 N12 2.908(2) . 2_554 no N3 N22 2.949(2) . 2_554 no N12 N22 3.068(2) . . no N12 N3 2.908(2) . 2_555 no N22 N12 3.068(2) . . no N22 N3 2.949(2) . 2_555 no N1 H15A 2.7925 . 7_555 no N1 H15A 2.7609 . 1_565 no N2 H15B 2.6953 . 1_565 no N3 H25A 2.8429 . 3_555 no N3 H12 2.08(2) . 2_554 no N3 H22 2.13(2) . 2_554 no N12 H22 2.90(2) . . no N22 H12 2.91(2) . . no C1 C14 3.509(2) . 1_565 no C1 C15 3.194(2) . 1_565 no C2 C2 3.401(2) . 7_555 no C2 C24 3.597(3) . 8_554 no C2 C2 3.401(2) . 7_545 no C2 N1 3.384(2) . 7_545 no C14 C1 3.509(2) . 1_545 no C15 C1 3.194(2) . 1_545 no C15 N2 3.406(2) . 1_545 no C15 N1 3.270(2) . 1_545 no C24 C2 3.597(3) . 8_555 no C1 H14B 3.0690 . 7_555 no C1 H15A 3.0047 . 1_565 no C1 H15B 2.7670 . 1_565 no C2 H22 3.07(2) . 8_554 no C2 H22 3.02(2) . 2_554 no C2 H15A 2.9615 . 7_555 no C2 H24A 3.0708 . 8_554 no C14 H25B 3.0980 . 1_545 no C23 H24B 3.0407 . 4_545 no C25 H14A 3.0746 . 1_565 no H12 N22 2.91(2) . . no H12 H22 2.51(3) . . no H12 N3 2.08(2) . 2_555 no H14A C25 3.0746 . 1_545 no H14B C1 3.0690 . 7_545 no H15A N1 2.7609 . 1_545 no H15A C1 3.0047 . 1_545 no H15A N1 2.7925 . 7_545 no H15A C2 2.9615 . 7_545 no H15B Ni1 3.6171 . 1_545 no H15B N2 2.6953 . 1_545 no H15B C1 2.7670 . 1_545 no H15B Ni1 3.6171 . 5_545 no H15B H15B 2.5121 . 5_545 no H22 N12 2.90(2) . . no H22 H12 2.51(3) . . no H22 N3 2.13(2) . 2_555 no H22 C2 3.02(2) . 2_555 no H22 C2 3.07(2) . 8_555 no H24A C2 3.0708 . 8_555 no H24B C23 3.0407 . 4_555 no H25A N3 2.8429 . 3_455 no H25B C14 3.0980 . 1_565 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N12 H12 N3 0.86(2) 2.08(2) 2.908(2) 161.8(18) 2_555 yes N22 H22 N3 0.87(2) 2.13(2) 2.949(2) 158.2(19) 2_555 yes #===END