Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 loop_ _publ_author_name 'Malcolm A. Halcrow' 'Colin Kilner' 'Stewart A. Leaver' 'Mallayan Palaniandavar' _publ_contact_author_name 'Dr Malcolm A. Halcrow' _publ_contact_author_address ; School of Chemistry University of Leeds Woodhouse Lane Leeds LS2 9JT UNITED KINGDOM ; _publ_contact_author_email M.A.HALCROW@CHEM.LEEDS.AC.UK _publ_section_title ; A new synthesis of bis(2-{pyrid-2-yl}ethyl)amine (LH) from bis(2-{pyrid-2-yl}ethyl)hydroxylamine (LOH), and a biomimetic copper-dependent reduction of LOH to LH ; data_mp4 _database_code_CSD 202131 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [Bis(2-{pyridin-2-yl}ethyl)amine]dichlorocopper(II) ; _chemical_name_common (Bis(2-(pyridin-2-yl)ethyl)amine)dichlorocopper(ii) _chemical_melting_point ? _chemical_formula_moiety 'C14 H17 Cl2 Cu N3' _chemical_formula_sum 'C14 H17 Cl2 Cu N3' _chemical_formula_weight 361.75 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 28.1563(4) _cell_length_b 7.7451(1) _cell_length_c 14.2271(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.4294(5) _cell_angle_gamma 90.00 _cell_volume 3004.69(7) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 45081 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 26.00 _exptl_crystal_description Block _exptl_crystal_colour Blue _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 1.802 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7614 _exptl_absorpt_correction_T_max 0.8996 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; The high merging-R value is probably a combination of the large number of reflections collected (giving a very redundant dataset), and the small, rather mosaic crystal (mosaicity was 0.60; a well-diffracting crystal would yield a value of ca. 0.45 under our conditions). Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD diffractometer' _diffrn_measurement_method 'Area detector scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45081 _diffrn_reflns_av_R_equivalents 0.1066 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5887 _reflns_number_gt 5099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _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. The asymmetric unit contains two crystallographically independent molecules lying on general positions. No disorder was detected during refinement, and no restraints were applied. All non-H atoms were refined anisotropically, while all H atoms were placed in calculated positions and refined using a riding model. There are two residual peaks in the Fourier difference map of 1.4 e.\%A^-3^. These each lie 2.2\%A from one of the two Cu atoms, and 1.0\%A away from the corresponding amine N atom (N2 or N22). These residual peaks could in principle correspond to ca. 0.2 of a N atom, and made us suspect that the C~2~H~5~NC~2~H~5~ portions of the ligands might be disordered. However, attempts to refine a disorder model based on partial occupancies of N2, C3, C11 and N22, N23, C31 with suitably restrained 1,2- and 1,3-interatomic distances were unsuccessful. In addition, such a putative minor disorder orientation for N2 and N22 would not yield a sensible coordination geometry at the Cu ions. Therefore, these two residual peaks were not included in the final model. ; _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^)+(0.0242P)^2^+24.5644P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5887 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.1655 _refine_ls_wR_factor_gt 0.1592 _refine_ls_goodness_of_fit_ref 1.218 _refine_ls_restrained_S_all 1.218 _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 Cu1 Cu 0.38165(3) 0.24680(10) 0.29835(5) 0.02281(19) Uani 1 1 d . . . N2 N 0.3875(2) 0.1163(8) 0.1764(4) 0.0396(14) Uani 1 1 d . . . H2 H 0.3754 0.1926 0.1255 0.048 Uiso 1 1 calc R . . C3 C 0.4368(3) 0.0728(10) 0.1679(5) 0.0402(17) Uani 1 1 d . . . H3A H 0.4537 0.1807 0.1577 0.048 Uiso 1 1 calc R . . H3B H 0.4339 -0.0001 0.1096 0.048 Uiso 1 1 calc R . . C4 C 0.4682(3) -0.0203(9) 0.2539(5) 0.0341(15) Uani 1 1 d . . . H4A H 0.4496 -0.1207 0.2689 0.041 Uiso 1 1 calc R . . H4B H 0.4976 -0.0654 0.2357 0.041 Uiso 1 1 calc R . . C5 C 0.4848(2) 0.0859(8) 0.3439(5) 0.0285(13) Uani 1 1 d . . . N6 N 0.45240(18) 0.1947(7) 0.3698(4) 0.0241(11) Uani 1 1 d . . . C7 C 0.4682(2) 0.2863(9) 0.4517(4) 0.0279(13) Uani 1 1 d . . . H7 H 0.4459 0.3640 0.4698 0.033 Uiso 1 1 calc R . . C8 C 0.5152(2) 0.2737(9) 0.5114(4) 0.0305(14) Uani 1 1 d . . . H8 H 0.5243 0.3381 0.5700 0.037 Uiso 1 1 calc R . . C9 C 0.5481(2) 0.1666(9) 0.4843(5) 0.0336(15) Uani 1 1 d . . . H9 H 0.5808 0.1571 0.5228 0.040 Uiso 1 1 calc R . . C10 C 0.5328(2) 0.0730(9) 0.4000(5) 0.0332(15) Uani 1 1 d . . . H10 H 0.5553 -0.0013 0.3799 0.040 Uiso 1 1 calc R . . C11 C 0.3535(3) -0.0401(9) 0.1542(5) 0.0433(18) Uani 1 1 d . . . H11A H 0.3731 -0.1463 0.1732 0.052 Uiso 1 1 calc R . . H11B H 0.3388 -0.0456 0.0834 0.052 Uiso 1 1 calc R . . C12 C 0.3123(3) -0.0353(11) 0.2069(6) 0.051(2) Uani 1 1 d . . . H12A H 0.2893 -0.1318 0.1834 0.062 Uiso 1 1 calc R . . H12B H 0.3265 -0.0524 0.2773 0.062 Uiso 1 1 calc R . . C13 C 0.2843(3) 0.1324(10) 0.1915(5) 0.0374(16) Uani 1 1 d . . . N14 N 0.31056(19) 0.2740(7) 0.2238(4) 0.0278(11) Uani 1 1 d . . . C15 C 0.2881(2) 0.4291(10) 0.2058(5) 0.0349(15) Uani 1 1 d . . . H15 H 0.3066 0.5305 0.2279 0.042 Uiso 1 1 calc R . . C16 C 0.2391(3) 0.4460(12) 0.1563(5) 0.0454(19) Uani 1 1 d . . . H16 H 0.2243 0.5568 0.1445 0.055 Uiso 1 1 calc R . . C17 C 0.2128(3) 0.3012(14) 0.1251(5) 0.053(2) Uani 1 1 d . . . H17 H 0.1792 0.3098 0.0917 0.063 Uiso 1 1 calc R . . C18 C 0.2352(3) 0.1398(13) 0.1421(6) 0.050(2) Uani 1 1 d . . . H18 H 0.2173 0.0374 0.1204 0.060 Uiso 1 1 calc R . . Cl19 Cl 0.35541(6) 0.2162(2) 0.44426(11) 0.0332(4) Uani 1 1 d . . . Cl20 Cl 0.40148(6) 0.5486(2) 0.28350(12) 0.0369(4) Uani 1 1 d . . . Cu21 Cu 0.11723(2) 0.72664(9) 0.41809(5) 0.02177(19) Uani 1 1 d . . . N22 N 0.1097(2) 0.6031(7) 0.2870(4) 0.0304(12) Uani 1 1 d . . . H22 H 0.1231 0.6789 0.2500 0.037 Uiso 1 1 calc R . . C23 C 0.0591(2) 0.5726(9) 0.2289(5) 0.0308(14) Uani 1 1 d . . . H23A H 0.0603 0.5041 0.1709 0.037 Uiso 1 1 calc R . . H23B H 0.0438 0.6851 0.2063 0.037 Uiso 1 1 calc R . . C24 C 0.0275(2) 0.4798(8) 0.2833(5) 0.0286(13) Uani 1 1 d . . . H24A H 0.0456 0.3776 0.3155 0.034 Uiso 1 1 calc R . . H24B H -0.0022 0.4375 0.2361 0.034 Uiso 1 1 calc R . . C25 C 0.0118(2) 0.5872(8) 0.3591(4) 0.0244(12) Uani 1 1 d . . . N26 N 0.04545(18) 0.6900(7) 0.4180(3) 0.0243(11) Uani 1 1 d . . . C27 C 0.0304(2) 0.7842(8) 0.4846(4) 0.0262(13) Uani 1 1 d . . . H27 H 0.0534 0.8594 0.5249 0.031 Uiso 1 1 calc R . . C28 C -0.0164(2) 0.7779(9) 0.4976(4) 0.0283(13) Uani 1 1 d . . . H28 H -0.0251 0.8451 0.5466 0.034 Uiso 1 1 calc R . . C29 C -0.0503(2) 0.6721(9) 0.4381(5) 0.0309(14) Uani 1 1 d . . . H29 H -0.0829 0.6648 0.4456 0.037 Uiso 1 1 calc R . . C30 C -0.0364(2) 0.5771(8) 0.3676(5) 0.0295(14) Uani 1 1 d . . . H30 H -0.0595 0.5052 0.3250 0.035 Uiso 1 1 calc R . . C31 C 0.1397(3) 0.4396(9) 0.2922(5) 0.0360(15) Uani 1 1 d . . . H31A H 0.1555 0.4374 0.2373 0.043 Uiso 1 1 calc R . . H31B H 0.1177 0.3382 0.2859 0.043 Uiso 1 1 calc R . . C32 C 0.1790(3) 0.4274(9) 0.3874(5) 0.0396(16) Uani 1 1 d . . . H32A H 0.1630 0.4141 0.4415 0.047 Uiso 1 1 calc R . . H32B H 0.1992 0.3232 0.3860 0.047 Uiso 1 1 calc R . . C33 C 0.2118(2) 0.5828(9) 0.4058(5) 0.0321(14) Uani 1 1 d . . . N34 N 0.18915(18) 0.7331(7) 0.4161(4) 0.0260(11) Uani 1 1 d . . . C35 C 0.2148(2) 0.8808(10) 0.4271(5) 0.0365(16) Uani 1 1 d . . . H35 H 0.1988 0.9867 0.4331 0.044 Uiso 1 1 calc R . . C36 C 0.2646(3) 0.8812(13) 0.4299(6) 0.050(2) Uani 1 1 d . . . H36 H 0.2826 0.9862 0.4380 0.060 Uiso 1 1 calc R . . C37 C 0.2874(3) 0.7263(13) 0.4207(5) 0.051(2) Uani 1 1 d . . . H37 H 0.3213 0.7239 0.4222 0.061 Uiso 1 1 calc R . . C38 C 0.2609(3) 0.5764(11) 0.4095(5) 0.0404(17) Uani 1 1 d . . . H38 H 0.2763 0.4690 0.4042 0.048 Uiso 1 1 calc R . . Cl39 Cl 0.14258(5) 0.7009(2) 0.58934(11) 0.0315(4) Uani 1 1 d . . . Cl40 Cl 0.10201(6) 1.0338(2) 0.38342(12) 0.0342(4) 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 Cu1 0.0219(4) 0.0236(4) 0.0223(4) -0.0008(3) 0.0043(3) 0.0000(3) N2 0.046(3) 0.037(3) 0.034(3) -0.002(3) 0.006(3) -0.002(3) C3 0.047(4) 0.040(4) 0.037(4) -0.006(3) 0.016(3) 0.006(3) C4 0.040(4) 0.023(3) 0.042(4) -0.004(3) 0.013(3) 0.002(3) C5 0.031(3) 0.021(3) 0.035(3) 0.003(3) 0.011(3) 0.002(3) N6 0.024(2) 0.022(3) 0.026(3) 0.004(2) 0.006(2) 0.003(2) C7 0.024(3) 0.034(4) 0.025(3) 0.000(3) 0.006(2) -0.002(3) C8 0.029(3) 0.035(4) 0.025(3) 0.005(3) 0.003(3) -0.004(3) C9 0.026(3) 0.032(4) 0.040(4) 0.011(3) 0.003(3) 0.000(3) C10 0.027(3) 0.029(3) 0.045(4) 0.007(3) 0.011(3) 0.006(3) C11 0.061(5) 0.025(4) 0.039(4) -0.005(3) 0.003(3) 0.000(3) C12 0.066(5) 0.044(5) 0.041(4) 0.000(4) 0.007(4) -0.023(4) C13 0.036(4) 0.046(4) 0.029(3) -0.005(3) 0.006(3) -0.015(3) N14 0.026(3) 0.033(3) 0.024(3) -0.002(2) 0.005(2) -0.004(2) C15 0.026(3) 0.042(4) 0.035(4) -0.005(3) 0.004(3) 0.005(3) C16 0.029(4) 0.068(6) 0.038(4) -0.004(4) 0.006(3) 0.013(4) C17 0.023(3) 0.095(7) 0.037(4) -0.021(4) 0.004(3) -0.001(4) C18 0.036(4) 0.071(6) 0.043(4) -0.019(4) 0.009(3) -0.023(4) Cl19 0.0292(8) 0.0448(10) 0.0262(7) -0.0007(7) 0.0080(6) -0.0027(7) Cl20 0.0330(8) 0.0324(9) 0.0408(9) 0.0049(7) 0.0007(7) -0.0051(7) Cu21 0.0195(3) 0.0222(4) 0.0238(4) -0.0025(3) 0.0056(3) -0.0013(3) N22 0.037(3) 0.022(3) 0.034(3) 0.000(2) 0.011(2) -0.001(2) C23 0.038(4) 0.025(3) 0.027(3) -0.005(3) 0.005(3) -0.001(3) C24 0.033(3) 0.020(3) 0.032(3) -0.005(3) 0.007(3) -0.003(3) C25 0.028(3) 0.017(3) 0.027(3) 0.003(2) 0.005(2) 0.001(2) N26 0.025(3) 0.024(3) 0.024(2) 0.003(2) 0.006(2) 0.003(2) C27 0.029(3) 0.026(3) 0.023(3) -0.004(2) 0.004(2) -0.001(3) C28 0.029(3) 0.031(3) 0.027(3) 0.001(3) 0.010(3) 0.000(3) C29 0.026(3) 0.029(3) 0.038(4) 0.009(3) 0.008(3) 0.002(3) C30 0.030(3) 0.024(3) 0.034(3) 0.004(3) 0.006(3) -0.001(3) C31 0.047(4) 0.028(4) 0.035(4) -0.004(3) 0.015(3) 0.004(3) C32 0.046(4) 0.029(4) 0.044(4) 0.005(3) 0.012(3) 0.009(3) C33 0.034(3) 0.038(4) 0.024(3) -0.001(3) 0.007(3) 0.007(3) N34 0.026(3) 0.025(3) 0.028(3) 0.000(2) 0.008(2) -0.002(2) C35 0.029(3) 0.033(4) 0.047(4) -0.002(3) 0.010(3) -0.012(3) C36 0.032(4) 0.066(6) 0.050(5) 0.002(4) 0.006(3) -0.019(4) C37 0.024(3) 0.091(7) 0.039(4) 0.011(4) 0.009(3) 0.003(4) C38 0.033(4) 0.054(5) 0.034(4) 0.003(3) 0.009(3) 0.010(3) Cl39 0.0265(7) 0.0413(9) 0.0258(7) 0.0000(6) 0.0047(6) 0.0020(7) Cl40 0.0352(8) 0.0263(8) 0.0433(9) 0.0055(7) 0.0138(7) 0.0010(7) _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 Cu1 N14 2.029(5) . ? Cu1 N6 2.038(5) . ? Cu1 N2 2.050(6) . ? Cu1 Cl19 2.3823(16) . ? Cu1 Cl20 2.4243(18) . ? N2 C3 1.463(9) . ? N2 C11 1.528(9) . ? C3 C4 1.503(10) . ? C4 C5 1.495(9) . ? C5 N6 1.358(8) . ? C5 C10 1.392(9) . ? N6 C7 1.342(8) . ? C7 C8 1.386(9) . ? C8 C9 1.369(10) . ? C9 C10 1.375(10) . ? C11 C12 1.531(12) . ? C12 C13 1.507(12) . ? C13 N14 1.339(9) . ? C13 C18 1.386(10) . ? N14 C15 1.352(9) . ? C15 C16 1.391(9) . ? C16 C17 1.356(12) . ? C17 C18 1.394(13) . ? Cu21 N34 2.033(5) . ? Cu21 N26 2.041(5) . ? Cu21 N22 2.059(5) . ? Cu21 Cl39 2.3705(16) . ? Cu21 Cl40 2.4459(18) . ? N22 C23 1.477(8) . ? N22 C31 1.514(8) . ? C23 C24 1.500(9) . ? C24 C25 1.512(8) . ? C25 N26 1.356(8) . ? C25 C30 1.394(9) . ? N26 C27 1.345(8) . ? C27 C28 1.377(9) . ? C28 C29 1.378(9) . ? C29 C30 1.378(9) . ? C31 C32 1.523(10) . ? C32 C33 1.500(10) . ? C33 N34 1.352(8) . ? C33 C38 1.371(9) . ? N34 C35 1.342(8) . ? C35 C36 1.391(10) . ? C36 C37 1.382(13) . ? C37 C38 1.368(12) . ? 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 N14 Cu1 N6 174.4(2) . . ? N14 Cu1 N2 83.4(2) . . ? N6 Cu1 N2 92.9(2) . . ? N14 Cu1 Cl19 89.22(15) . . ? N6 Cu1 Cl19 91.30(14) . . ? N2 Cu1 Cl19 142.80(19) . . ? N14 Cu1 Cl20 94.17(16) . . ? N6 Cu1 Cl20 90.94(15) . . ? N2 Cu1 Cl20 109.42(18) . . ? Cl19 Cu1 Cl20 107.45(7) . . ? C3 N2 C11 111.0(6) . . ? C3 N2 Cu1 117.5(4) . . ? C11 N2 Cu1 112.8(4) . . ? N2 C3 C4 115.0(6) . . ? C5 C4 C3 115.3(6) . . ? N6 C5 C10 120.8(6) . . ? N6 C5 C4 119.1(6) . . ? C10 C5 C4 120.2(6) . . ? C7 N6 C5 117.6(5) . . ? C7 N6 Cu1 113.5(4) . . ? C5 N6 Cu1 128.8(4) . . ? N6 C7 C8 123.7(6) . . ? C9 C8 C7 118.6(6) . . ? C8 C9 C10 118.6(6) . . ? C9 C10 C5 120.7(6) . . ? N2 C11 C12 113.1(6) . . ? C13 C12 C11 112.5(6) . . ? N14 C13 C18 122.4(8) . . ? N14 C13 C12 115.6(6) . . ? C18 C13 C12 121.9(7) . . ? C13 N14 C15 118.1(6) . . ? C13 N14 Cu1 118.9(5) . . ? C15 N14 Cu1 123.0(4) . . ? N14 C15 C16 122.5(7) . . ? C17 C16 C15 118.7(8) . . ? C16 C17 C18 119.8(7) . . ? C13 C18 C17 118.5(7) . . ? N34 Cu21 N26 173.3(2) . . ? N34 Cu21 N22 83.0(2) . . ? N26 Cu21 N22 93.2(2) . . ? N34 Cu21 Cl39 88.30(15) . . ? N26 Cu21 Cl39 91.91(14) . . ? N22 Cu21 Cl39 145.92(16) . . ? N34 Cu21 Cl40 95.66(15) . . ? N26 Cu21 Cl40 90.66(15) . . ? N22 Cu21 Cl40 107.23(16) . . ? Cl39 Cu21 Cl40 106.38(6) . . ? C23 N22 C31 110.0(5) . . ? C23 N22 Cu21 116.7(4) . . ? C31 N22 Cu21 114.5(4) . . ? N22 C23 C24 113.6(5) . . ? C23 C24 C25 114.9(5) . . ? N26 C25 C30 121.6(6) . . ? N26 C25 C24 118.7(5) . . ? C30 C25 C24 119.6(5) . . ? C27 N26 C25 117.4(5) . . ? C27 N26 Cu21 114.2(4) . . ? C25 N26 Cu21 128.4(4) . . ? N26 C27 C28 123.7(6) . . ? C27 C28 C29 118.6(6) . . ? C28 C29 C30 119.0(6) . . ? C29 C30 C25 119.6(6) . . ? N22 C31 C32 111.6(5) . . ? C33 C32 C31 112.6(6) . . ? N34 C33 C38 121.7(7) . . ? N34 C33 C32 115.1(6) . . ? C38 C33 C32 123.2(7) . . ? C35 N34 C33 119.4(6) . . ? C35 N34 Cu21 122.0(5) . . ? C33 N34 Cu21 118.6(4) . . ? N34 C35 C36 121.0(7) . . ? C37 C36 C35 118.9(8) . . ? C38 C37 C36 119.7(7) . . ? C37 C38 C33 119.2(7) . . ? 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 N2 H2 Cl19 0.93 2.60 3.452(6) 153.1 4_565 N22 H22 Cl39 0.93 2.65 3.518(6) 155.8 4_575 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.442 _refine_diff_density_min -0.909 _refine_diff_density_rms 0.192 data_mh80 _database_code_CSD 218093 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [Bis(2-{pyridin-2-yl}ethyl)hydroxylamine]dichlorocobalt(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H17 Cl2 Co N3 O' _chemical_formula_sum 'C14 H17 Cl2 Co N3 O' _chemical_formula_weight 373.14 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.3446(1) _cell_length_b 15.4679(2) _cell_length_c 15.2653(2) _cell_angle_alpha 90.00 _cell_angle_beta 118.1960(5) _cell_angle_gamma 90.00 _cell_volume 1528.43(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 29914 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 27.49 _exptl_crystal_description Prism _exptl_crystal_colour Purple _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 1.473 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.493 _exptl_absorpt_correction_T_max 0.719 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD diffractometer' _diffrn_measurement_method 'Area detector scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29914 _diffrn_reflns_av_R_equivalents 0.0703 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3483 _reflns_number_gt 3312 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _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. No disorder was detected during refinement, and no restraints were applied. All non-H atoms were refined anisotropically, while all C-bound H atoms were placed in calculated positions and refined using a riding model. The hydroxyl H atom H19 was located in the difference map and allowed to refine freely. ; _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^)+(0.0349P)^2^+0.6100P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0110(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3483 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0705 _refine_ls_wR_factor_gt 0.0694 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 Co1 Co -0.27174(3) -0.133517(12) 0.217318(13) 0.02175(9) Uani 1 1 d . . . N2 N -0.03777(17) -0.07459(8) 0.19645(9) 0.0238(2) Uani 1 1 d . . . C3 C 0.0643(2) -0.00649(10) 0.27278(12) 0.0305(3) Uani 1 1 d . . . H3A H -0.0434 0.0307 0.2747 0.037 Uiso 1 1 calc R . . H3B H 0.1489 0.0302 0.2528 0.037 Uiso 1 1 calc R . . C4 C 0.2016(2) -0.04155(11) 0.37661(12) 0.0351(4) Uani 1 1 d . . . H4A H 0.2979 -0.0839 0.3720 0.042 Uiso 1 1 calc R . . H4B H 0.2860 0.0069 0.4184 0.042 Uiso 1 1 calc R . . C5 C 0.0986(2) -0.08443(10) 0.43025(11) 0.0290(3) Uani 1 1 d . . . N6 N -0.09191(19) -0.11818(8) 0.37755(9) 0.0253(3) Uani 1 1 d . . . C7 C -0.1823(3) -0.15358(10) 0.42818(11) 0.0302(3) Uani 1 1 d . . . H7 H -0.3189 -0.1754 0.3914 0.036 Uiso 1 1 calc R . . C8 C -0.0867(3) -0.15987(11) 0.53079(12) 0.0369(4) Uani 1 1 d . . . H8 H -0.1556 -0.1852 0.5637 0.044 Uiso 1 1 calc R . . C9 C 0.1136(3) -0.12787(11) 0.58436(13) 0.0406(4) Uani 1 1 d . . . H9 H 0.1862 -0.1328 0.6547 0.049 Uiso 1 1 calc R . . C10 C 0.2044(3) -0.08899(12) 0.53366(12) 0.0375(4) Uani 1 1 d . . . H10 H 0.3392 -0.0652 0.5692 0.045 Uiso 1 1 calc R . . C11 C -0.1183(2) -0.03494(10) 0.09602(12) 0.0309(3) Uani 1 1 d . . . H11A H -0.0055 -0.0020 0.0933 0.037 Uiso 1 1 calc R . . H11B H -0.2290 0.0066 0.0861 0.037 Uiso 1 1 calc R . . C12 C -0.2028(2) -0.09962(12) 0.01194(11) 0.0331(3) Uani 1 1 d . . . H12A H -0.2109 -0.0713 -0.0480 0.040 Uiso 1 1 calc R . . H12B H -0.1030 -0.1479 0.0296 0.040 Uiso 1 1 calc R . . C13 C -0.4111(2) -0.13686(9) -0.01438(11) 0.0254(3) Uani 1 1 d . . . N14 N -0.46627(19) -0.14481(8) 0.05764(9) 0.0249(3) Uani 1 1 d . . . C15 C -0.6570(2) -0.17546(10) 0.03168(11) 0.0283(3) Uani 1 1 d . . . H15 H -0.6974 -0.1810 0.0821 0.034 Uiso 1 1 calc R . . C16 C -0.7964(2) -0.19914(10) -0.06362(11) 0.0295(3) Uani 1 1 d . . . H16 H -0.9307 -0.2187 -0.0789 0.035 Uiso 1 1 calc R . . C17 C -0.7360(3) -0.19380(10) -0.13717(11) 0.0309(3) Uani 1 1 d . . . H17 H -0.8267 -0.2116 -0.2033 0.037 Uiso 1 1 calc R . . C18 C -0.5421(2) -0.16214(10) -0.11224(11) 0.0299(3) Uani 1 1 d . . . H18 H -0.4978 -0.1576 -0.1613 0.036 Uiso 1 1 calc R . . O19 O 0.11198(17) -0.13946(7) 0.20647(9) 0.0292(2) Uani 1 1 d . . . H19 H 0.227(3) -0.1128(16) 0.2100(16) 0.054(7) Uiso 1 1 d . . . Cl20 Cl -0.50920(5) -0.03520(2) 0.22254(3) 0.02931(11) Uani 1 1 d . . . Cl21 Cl -0.29254(6) -0.28123(2) 0.22737(3) 0.02997(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.02002(13) 0.02433(13) 0.02224(13) 0.00125(6) 0.01108(9) -0.00117(6) N2 0.0212(5) 0.0243(6) 0.0277(6) 0.0020(5) 0.0131(5) 0.0010(4) C3 0.0302(7) 0.0273(7) 0.0385(8) -0.0067(6) 0.0200(7) -0.0065(6) C4 0.0259(7) 0.0446(9) 0.0330(8) -0.0116(7) 0.0125(6) -0.0067(6) C5 0.0264(7) 0.0303(7) 0.0269(7) -0.0058(6) 0.0099(6) 0.0030(6) N6 0.0261(6) 0.0263(6) 0.0235(6) -0.0007(5) 0.0116(5) 0.0019(5) C7 0.0363(8) 0.0293(7) 0.0276(7) 0.0000(6) 0.0173(7) 0.0017(6) C8 0.0530(10) 0.0333(8) 0.0297(8) 0.0014(6) 0.0238(8) 0.0053(7) C9 0.0480(10) 0.0442(10) 0.0225(7) -0.0022(6) 0.0107(7) 0.0098(7) C10 0.0330(8) 0.0426(9) 0.0285(8) -0.0082(7) 0.0077(7) 0.0028(7) C11 0.0264(7) 0.0330(8) 0.0337(8) 0.0093(6) 0.0145(6) -0.0014(6) C12 0.0271(7) 0.0502(9) 0.0257(7) 0.0059(7) 0.0154(6) 0.0001(7) C13 0.0262(7) 0.0280(7) 0.0238(7) 0.0045(5) 0.0134(6) 0.0041(5) N14 0.0248(6) 0.0288(6) 0.0222(6) 0.0025(5) 0.0119(5) -0.0005(5) C15 0.0278(7) 0.0336(8) 0.0247(7) 0.0002(6) 0.0133(6) -0.0048(6) C16 0.0288(7) 0.0287(7) 0.0286(7) -0.0012(6) 0.0117(6) -0.0053(6) C17 0.0364(8) 0.0282(7) 0.0237(7) -0.0030(6) 0.0106(6) -0.0020(6) C18 0.0361(8) 0.0318(7) 0.0245(7) 0.0020(6) 0.0164(6) 0.0035(6) O19 0.0250(5) 0.0278(5) 0.0360(6) 0.0008(4) 0.0155(5) 0.0030(4) Cl20 0.02407(18) 0.03132(19) 0.0323(2) -0.00106(13) 0.01317(15) 0.00273(13) Cl21 0.0335(2) 0.02529(18) 0.02816(19) 0.00097(13) 0.01215(16) -0.00137(13) _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 Co1 N2 2.0982(12) . ? Co1 N14 2.1731(12) . ? Co1 N6 2.1751(13) . ? Co1 Cl21 2.2999(4) . ? Co1 Cl20 2.3435(4) . ? N2 O19 1.4426(15) . ? N2 C3 1.4845(19) . ? N2 C11 1.4898(18) . ? C3 C4 1.521(2) . ? C4 C5 1.506(2) . ? C5 N6 1.3465(19) . ? C5 C10 1.393(2) . ? N6 C7 1.350(2) . ? C7 C8 1.384(2) . ? C8 C9 1.393(3) . ? C9 C10 1.376(3) . ? C11 C12 1.510(2) . ? C12 C13 1.501(2) . ? C13 N14 1.3452(19) . ? C13 C18 1.397(2) . ? N14 C15 1.3491(19) . ? C15 C16 1.375(2) . ? C16 C17 1.391(2) . ? C17 C18 1.379(2) . ? O19 H19 0.92(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 N2 Co1 N14 90.93(5) . . ? N2 Co1 N6 91.01(5) . . ? N14 Co1 N6 176.61(5) . . ? N2 Co1 Cl21 121.78(3) . . ? N14 Co1 Cl21 88.04(3) . . ? N6 Co1 Cl21 93.30(3) . . ? N2 Co1 Cl20 113.54(3) . . ? N14 Co1 Cl20 89.13(3) . . ? N6 Co1 Cl20 87.55(3) . . ? Cl21 Co1 Cl20 124.640(15) . . ? O19 N2 C3 109.48(11) . . ? O19 N2 C11 107.90(11) . . ? C3 N2 C11 108.86(12) . . ? O19 N2 Co1 108.65(8) . . ? C3 N2 Co1 109.58(9) . . ? C11 N2 Co1 112.32(9) . . ? N2 C3 C4 113.90(13) . . ? C5 C4 C3 117.88(13) . . ? N6 C5 C10 121.54(15) . . ? N6 C5 C4 119.53(13) . . ? C10 C5 C4 118.92(14) . . ? C5 N6 C7 117.93(13) . . ? C5 N6 Co1 128.43(11) . . ? C7 N6 Co1 113.45(10) . . ? N6 C7 C8 123.53(16) . . ? C7 C8 C9 118.02(17) . . ? C10 C9 C8 118.88(15) . . ? C9 C10 C5 120.02(16) . . ? N2 C11 C12 113.94(12) . . ? C13 C12 C11 116.07(13) . . ? N14 C13 C18 121.81(14) . . ? N14 C13 C12 118.61(13) . . ? C18 C13 C12 119.57(13) . . ? C13 N14 C15 117.65(13) . . ? C13 N14 Co1 128.11(10) . . ? C15 N14 Co1 113.51(9) . . ? N14 C15 C16 123.70(14) . . ? C15 C16 C17 118.47(14) . . ? C18 C17 C16 118.68(14) . . ? C17 C18 C13 119.61(14) . . ? N2 O19 H19 109.2(15) . . ? 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 O19 H19 Cl20 0.92(2) 2.21(2) 3.1236(12) 174(2) 1_655 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.325 _refine_diff_density_min -0.477 _refine_diff_density_rms 0.071