# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Karl Wieghardt' _publ_contact_author_email WIEGHARDT@MPI-MUELHEIM.MPG.DE _publ_section_title ; Redox-Noninnocence of N,N'-Bis(6-methyl-2-pyridylmethylene) -ethane-1,2-diamine (L): Synthesis and Characterization of Diamagnetic [NiII2(L**)2] and [ZnII2(L)Cl4] ((L**)2- = pi Diradical Dianion of L) ; loop_ _publ_author_name 'Karl Wieghardt' 'Amrita Mondal' 'Thomas Weyhermuller' # Attachment 'Mondal1_TW.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 735552' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H36 N8 Ni2, 0.5(C4 H10 O)' _chemical_formula_sum 'C34 H41 N8 Ni2 O0.50' _chemical_formula_weight 687.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.529(2) _cell_length_b 8.8499(9) _cell_length_c 20.938(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.060(2) _cell_angle_gamma 90.00 _cell_volume 3223.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9539 _cell_measurement_theta_min 2.813 _cell_measurement_theta_max 35.740 _exptl_crystal_description 'opaque parallelepiped' _exptl_crystal_colour 'dark violet' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1444 _exptl_absorpt_coefficient_mu 1.207 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8492 _exptl_absorpt_correction_T_max 0.9647 _exptl_absorpt_process_details 'SADABS Vers. 2008/1, Bruker AXS (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode + INCOATEC Muti-Layer-Optics' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 96839 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 32.50 _reflns_number_total 11664 _reflns_number_gt 10026 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAINT 7.34a' _computing_cell_refinement 'Bruker SAINT 7.34a' _computing_data_reduction 'Bruker SAINT 7.34a' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0338P)^2^+1.3089P] 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 11664 _refine_ls_number_parameters 428 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.168605(8) 0.347474(15) 0.181745(7) 0.01698(4) Uani 1 1 d . . . Ni2 Ni 0.323278(8) 0.553304(16) 0.096727(7) 0.01719(4) Uani 1 1 d . . . N1 N 0.05693(6) 0.33504(10) 0.17294(5) 0.01831(17) Uani 1 1 d . . . C2 C 0.01143(7) 0.21028(13) 0.16902(6) 0.0221(2) Uani 1 1 d . . . C3 C -0.06739(7) 0.22016(16) 0.16746(6) 0.0288(3) Uani 1 1 d . . . H3 H -0.0975 0.1307 0.1659 0.035 Uiso 1 1 calc R . . C4 C -0.10309(7) 0.36192(17) 0.16817(6) 0.0294(3) Uani 1 1 d . . . H4 H -0.1573 0.3696 0.1673 0.035 Uiso 1 1 calc R . . C5 C -0.05843(7) 0.48880(16) 0.17015(6) 0.0268(2) Uani 1 1 d . . . H5 H -0.0814 0.5861 0.1695 0.032 Uiso 1 1 calc R . . C6 C 0.02193(7) 0.47430(13) 0.17320(6) 0.0206(2) Uani 1 1 d . . . C7 C 0.07464(7) 0.59576(13) 0.17896(6) 0.0220(2) Uani 1 1 d . . . H7 H 0.0580 0.6979 0.1792 0.026 Uiso 1 1 calc R . . N8 N 0.14838(6) 0.55973(10) 0.18396(5) 0.01982(17) Uani 1 1 d . . . C9 C 0.20301(7) 0.68552(13) 0.19034(6) 0.0246(2) Uani 1 1 d . . . H9A H 0.1808 0.7702 0.2128 0.029 Uiso 1 1 calc R . . H9B H 0.2114 0.7212 0.1469 0.029 Uiso 1 1 calc R . . C10 C 0.27968(7) 0.64146(14) 0.22725(6) 0.0247(2) Uani 1 1 d . . . H10A H 0.3083 0.7341 0.2419 0.030 Uiso 1 1 calc R . . H10B H 0.2705 0.5829 0.2659 0.030 Uiso 1 1 calc R . . N11 N 0.32637(6) 0.55116(11) 0.18822(5) 0.02049(17) Uani 1 1 d . . . C12 C 0.37930(7) 0.46136(13) 0.21847(6) 0.0222(2) Uani 1 1 d . . . H12 H 0.3844 0.4478 0.2638 0.027 Uiso 1 1 calc R . . C13 C 0.42783(6) 0.38654(13) 0.17934(5) 0.01980(19) Uani 1 1 d . . . C14 C 0.48981(7) 0.29135(14) 0.20170(6) 0.0244(2) Uani 1 1 d . . . H14 H 0.5007 0.2684 0.2462 0.029 Uiso 1 1 calc R . . C15 C 0.53422(7) 0.23234(14) 0.15834(7) 0.0264(2) Uani 1 1 d . . . H15 H 0.5772 0.1705 0.1727 0.032 Uiso 1 1 calc R . . C16 C 0.51567(6) 0.26403(13) 0.09253(6) 0.0233(2) Uani 1 1 d . . . H16 H 0.5463 0.2243 0.0621 0.028 Uiso 1 1 calc R . . C17 C 0.45267(6) 0.35320(12) 0.07228(6) 0.01826(19) Uani 1 1 d . . . N18 N 0.40952(5) 0.41715(10) 0.11483(5) 0.01747(16) Uani 1 1 d . . . C19 C 0.05172(8) 0.06160(14) 0.16609(7) 0.0289(2) Uani 1 1 d . . . H19A H 0.0744 0.0547 0.1257 0.043 Uiso 1 1 calc R . . H19B H 0.0147 -0.0207 0.1682 0.043 Uiso 1 1 calc R . . H19C H 0.0924 0.0536 0.2025 0.043 Uiso 1 1 calc R . . C20 C 0.42655(7) 0.38106(14) 0.00246(6) 0.0219(2) Uani 1 1 d . . . H20A H 0.3777 0.3287 -0.0100 0.033 Uiso 1 1 calc R . . H20B H 0.4653 0.3429 -0.0234 0.033 Uiso 1 1 calc R . . H20C H 0.4195 0.4898 -0.0049 0.033 Uiso 1 1 calc R . . N21 N 0.23176(5) 0.23632(10) 0.24879(5) 0.01786(16) Uani 1 1 d . . . C22 C 0.22957(6) 0.23797(12) 0.31361(6) 0.01944(19) Uani 1 1 d . . . C23 C 0.27810(7) 0.15098(14) 0.35540(6) 0.0249(2) Uani 1 1 d . . . H23 H 0.2741 0.1528 0.4002 0.030 Uiso 1 1 calc R . . C24 C 0.33379(8) 0.05920(14) 0.33125(7) 0.0280(2) Uani 1 1 d . . . H24 H 0.3679 -0.0007 0.3595 0.034 Uiso 1 1 calc R . . C25 C 0.33786(7) 0.05779(13) 0.26628(7) 0.0251(2) Uani 1 1 d . . . H25 H 0.3756 -0.0018 0.2492 0.030 Uiso 1 1 calc R . . C26 C 0.28585(6) 0.14513(12) 0.22513(6) 0.01970(19) Uani 1 1 d . . . C27 C 0.28249(7) 0.15077(12) 0.15708(6) 0.0213(2) Uani 1 1 d . . . H27 H 0.3163 0.0932 0.1345 0.026 Uiso 1 1 calc R . . N28 N 0.22975(6) 0.24062(10) 0.12702(5) 0.01947(17) Uani 1 1 d . . . C29 C 0.22102(8) 0.23990(13) 0.05656(6) 0.0243(2) Uani 1 1 d . . . H29A H 0.1885 0.1530 0.0406 0.029 Uiso 1 1 calc R . . H29B H 0.2721 0.2266 0.0418 0.029 Uiso 1 1 calc R . . C30 C 0.18491(7) 0.38456(13) 0.02824(6) 0.0222(2) Uani 1 1 d . . . H30A H 0.1651 0.3670 -0.0175 0.027 Uiso 1 1 calc R . . H30B H 0.1407 0.4113 0.0513 0.027 Uiso 1 1 calc R . . N31 N 0.23876(5) 0.51139(11) 0.03239(5) 0.01896(17) Uani 1 1 d . . . C32 C 0.22877(6) 0.61161(13) -0.01480(6) 0.0208(2) Uani 1 1 d . . . H32 H 0.1897 0.6002 -0.0502 0.025 Uiso 1 1 calc R . . C33 C 0.27947(6) 0.73679(12) -0.00972(6) 0.01967(19) Uani 1 1 d . . . C34 C 0.27772(7) 0.85546(13) -0.05452(6) 0.0243(2) Uani 1 1 d . . . H34 H 0.2409 0.8552 -0.0918 0.029 Uiso 1 1 calc R . . C35 C 0.32955(8) 0.97167(13) -0.04389(7) 0.0259(2) Uani 1 1 d . . . H35 H 0.3293 1.0528 -0.0736 0.031 Uiso 1 1 calc R . . C36 C 0.38330(7) 0.96806(13) 0.01211(6) 0.0237(2) Uani 1 1 d . . . H36 H 0.4195 1.0476 0.0204 0.028 Uiso 1 1 calc R . . C37 C 0.38335(6) 0.84945(12) 0.05469(6) 0.01960(19) Uani 1 1 d . . . N38 N 0.33230(5) 0.73313(10) 0.04472(5) 0.01768(16) Uani 1 1 d . . . C39 C 0.17244(7) 0.34401(13) 0.33703(6) 0.0236(2) Uani 1 1 d . . . H39A H 0.1889 0.4485 0.3314 0.035 Uiso 1 1 calc R . . H39B H 0.1692 0.3250 0.3827 0.035 Uiso 1 1 calc R . . H39C H 0.1219 0.3279 0.3123 0.035 Uiso 1 1 calc R . . C40 C 0.43891(7) 0.84020(14) 0.11509(6) 0.0254(2) Uani 1 1 d . . . H40A H 0.4104 0.8383 0.1525 0.038 Uiso 1 1 calc R . . H40B H 0.4729 0.9284 0.1178 0.038 Uiso 1 1 calc R . . H40C H 0.4696 0.7479 0.1144 0.038 Uiso 1 1 calc R . . C41 C 0.0263(2) 0.7177(4) 0.00863(19) 0.0383(7) Uani 0.50 1 d PD . . H41A H 0.0697 0.6472 0.0114 0.057 Uiso 0.50 1 calc PR . . H41B H -0.0100 0.6939 -0.0295 0.057 Uiso 0.50 1 calc PR . . H41C H 0.0003 0.7083 0.0473 0.057 Uiso 0.50 1 calc PR . . C42 C 0.05524(14) 0.8766(3) 0.00348(14) 0.0303(5) Uani 0.50 1 d PD . . H42A H 0.0922 0.9012 0.0417 0.036 Uiso 0.50 1 calc PR . . H42B H 0.0821 0.8866 -0.0352 0.036 Uiso 0.50 1 calc PR . . O43 O -0.0077(2) 0.9769(2) -0.0007(3) 0.0305(7) Uani 0.50 1 d PD . . C45 C -0.0576(3) 1.2253(5) -0.0154(2) 0.0535(10) Uani 0.50 1 d PD . . H45A H -0.0437 1.3307 -0.0225 0.080 Uiso 0.50 1 calc PR . . H45B H -0.0808 1.2176 0.0247 0.080 Uiso 0.50 1 calc PR . . H45C H -0.0946 1.1909 -0.0514 0.080 Uiso 0.50 1 calc PR . . C44 C 0.01321(18) 1.1284(4) -0.01098(16) 0.0381(6) Uani 0.50 1 d PD . . H44A H 0.0371 1.1362 -0.0513 0.046 Uiso 0.50 1 calc PR . . H44B H 0.0510 1.1632 0.0250 0.046 Uiso 0.50 1 calc PR . . 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 0.02030(7) 0.01328(6) 0.01737(7) -0.00043(5) 0.00237(5) 0.00190(4) Ni2 0.01880(7) 0.01712(6) 0.01497(7) 0.00059(5) -0.00065(5) -0.00002(5) N1 0.0233(4) 0.0179(4) 0.0135(4) 0.0007(3) 0.0015(3) 0.0009(3) C2 0.0273(5) 0.0221(5) 0.0161(5) 0.0016(4) 0.0000(4) -0.0035(4) C3 0.0268(6) 0.0347(6) 0.0240(6) 0.0029(5) -0.0003(4) -0.0077(5) C4 0.0221(5) 0.0438(7) 0.0218(6) 0.0036(5) 0.0007(4) 0.0000(5) C5 0.0244(5) 0.0324(6) 0.0233(6) 0.0025(5) 0.0017(4) 0.0073(5) C6 0.0234(5) 0.0210(5) 0.0172(5) 0.0012(4) 0.0023(4) 0.0044(4) C7 0.0283(5) 0.0158(4) 0.0222(5) 0.0007(4) 0.0039(4) 0.0047(4) N8 0.0253(4) 0.0148(4) 0.0197(4) -0.0008(3) 0.0038(3) 0.0009(3) C9 0.0308(6) 0.0144(4) 0.0293(6) -0.0026(4) 0.0071(5) -0.0017(4) C10 0.0305(6) 0.0227(5) 0.0214(5) -0.0073(4) 0.0048(4) -0.0054(4) N11 0.0244(4) 0.0192(4) 0.0177(4) -0.0025(3) 0.0019(3) -0.0043(3) C12 0.0280(5) 0.0222(5) 0.0152(5) -0.0003(4) -0.0016(4) -0.0066(4) C13 0.0223(5) 0.0182(4) 0.0174(5) 0.0016(4) -0.0039(4) -0.0048(4) C14 0.0260(5) 0.0219(5) 0.0226(5) 0.0055(4) -0.0080(4) -0.0043(4) C15 0.0224(5) 0.0201(5) 0.0340(7) 0.0038(5) -0.0075(4) -0.0002(4) C16 0.0193(5) 0.0200(5) 0.0298(6) 0.0002(4) -0.0007(4) -0.0001(4) C17 0.0177(4) 0.0163(4) 0.0201(5) 0.0010(4) -0.0002(4) -0.0028(3) N18 0.0186(4) 0.0165(4) 0.0164(4) 0.0014(3) -0.0015(3) -0.0022(3) C19 0.0372(6) 0.0193(5) 0.0296(6) -0.0002(4) 0.0020(5) -0.0037(4) C20 0.0222(5) 0.0241(5) 0.0193(5) 0.0008(4) 0.0023(4) -0.0009(4) N21 0.0204(4) 0.0131(3) 0.0201(4) -0.0010(3) 0.0024(3) 0.0009(3) C22 0.0232(5) 0.0154(4) 0.0195(5) -0.0009(4) 0.0016(4) -0.0004(4) C23 0.0304(6) 0.0219(5) 0.0213(5) 0.0012(4) -0.0015(4) 0.0019(4) C24 0.0306(6) 0.0217(5) 0.0297(6) 0.0013(5) -0.0049(5) 0.0061(4) C25 0.0250(5) 0.0183(5) 0.0313(6) -0.0013(4) 0.0006(4) 0.0051(4) C26 0.0212(5) 0.0138(4) 0.0241(5) -0.0018(4) 0.0030(4) 0.0012(3) C27 0.0248(5) 0.0158(4) 0.0242(5) -0.0031(4) 0.0063(4) 0.0010(4) N28 0.0249(4) 0.0154(4) 0.0186(4) -0.0016(3) 0.0047(3) -0.0013(3) C29 0.0362(6) 0.0186(5) 0.0186(5) -0.0037(4) 0.0056(4) -0.0030(4) C30 0.0240(5) 0.0233(5) 0.0186(5) -0.0012(4) -0.0003(4) -0.0059(4) N31 0.0195(4) 0.0184(4) 0.0185(4) -0.0008(3) 0.0009(3) -0.0013(3) C32 0.0206(5) 0.0213(5) 0.0194(5) 0.0009(4) -0.0022(4) 0.0004(4) C33 0.0207(4) 0.0181(4) 0.0196(5) 0.0010(4) 0.0000(4) 0.0021(4) C34 0.0280(5) 0.0215(5) 0.0221(5) 0.0045(4) -0.0018(4) 0.0027(4) C35 0.0317(6) 0.0182(5) 0.0276(6) 0.0052(4) 0.0029(5) 0.0027(4) C36 0.0268(5) 0.0169(4) 0.0272(6) 0.0000(4) 0.0028(4) -0.0009(4) C37 0.0201(4) 0.0173(4) 0.0212(5) -0.0025(4) 0.0019(4) 0.0010(3) N38 0.0191(4) 0.0168(4) 0.0169(4) -0.0010(3) 0.0011(3) 0.0012(3) C39 0.0289(5) 0.0217(5) 0.0206(5) -0.0019(4) 0.0049(4) 0.0024(4) C40 0.0266(5) 0.0239(5) 0.0243(6) -0.0021(4) -0.0024(4) -0.0033(4) C41 0.0406(18) 0.0405(18) 0.0335(17) 0.0029(14) 0.0033(13) -0.0005(13) C42 0.0244(11) 0.0364(14) 0.0299(13) -0.0078(11) 0.0034(9) 0.0028(10) O43 0.0270(15) 0.036(2) 0.0292(9) 0.0001(19) 0.0045(13) 0.0044(13) C45 0.069(3) 0.055(3) 0.038(2) 0.0045(19) 0.011(2) 0.026(2) C44 0.0428(16) 0.0410(17) 0.0304(15) -0.0017(13) 0.0042(12) 0.0042(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 Ni1 N28 1.9125(10) . ? Ni1 N8 1.9132(9) . ? Ni1 N21 1.9447(10) . ? Ni1 N1 1.9467(10) . ? Ni2 N11 1.9098(10) . ? Ni2 N31 1.9123(10) . ? Ni2 N18 1.9340(10) . ? Ni2 N38 1.9457(10) . ? N1 C2 1.3585(15) . ? N1 C6 1.3769(14) . ? C2 C3 1.3808(18) . ? C2 C19 1.4982(18) . ? C3 C4 1.403(2) . ? C4 C5 1.367(2) . ? C5 C6 1.4081(16) . ? C6 C7 1.4128(17) . ? C7 N8 1.3231(15) . ? N8 C9 1.4637(15) . ? C9 C10 1.5167(19) . ? C10 N11 1.4632(15) . ? N11 C12 1.3225(16) . ? C12 C13 1.4160(17) . ? C13 N18 1.3763(14) . ? C13 C14 1.4085(16) . ? C14 C15 1.370(2) . ? C15 C16 1.4046(19) . ? C16 C17 1.3809(15) . ? C17 N18 1.3608(15) . ? C17 C20 1.4976(16) . ? N21 C22 1.3627(15) . ? N21 C26 1.3824(14) . ? C22 C23 1.3781(16) . ? C22 C39 1.4981(16) . ? C23 C24 1.4107(18) . ? C24 C25 1.371(2) . ? C25 C26 1.4063(17) . ? C26 C27 1.4197(17) . ? C27 N28 1.3191(15) . ? N28 C29 1.4645(15) . ? C29 C30 1.5162(17) . ? C30 N31 1.4622(15) . ? N31 C32 1.3232(15) . ? C32 C33 1.4160(16) . ? C33 N38 1.3778(14) . ? C33 C34 1.4059(16) . ? C34 C35 1.3722(18) . ? C35 C36 1.4113(18) . ? C36 C37 1.3771(16) . ? C37 N38 1.3632(14) . ? C37 C40 1.5007(17) . ? C41 C42 1.504(4) . ? C42 O43 1.410(4) . ? O43 C44 1.413(3) . ? C45 C44 1.503(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N28 Ni1 N8 128.25(4) . . ? N28 Ni1 N21 82.59(4) . . ? N8 Ni1 N21 124.74(4) . . ? N28 Ni1 N1 123.12(4) . . ? N8 Ni1 N1 82.57(4) . . ? N21 Ni1 N1 121.09(4) . . ? N11 Ni2 N31 128.96(4) . . ? N11 Ni2 N18 82.65(4) . . ? N31 Ni2 N18 122.45(4) . . ? N11 Ni2 N38 125.12(4) . . ? N31 Ni2 N38 82.74(4) . . ? N18 Ni2 N38 120.26(4) . . ? C2 N1 C6 117.98(10) . . ? C2 N1 Ni1 128.88(8) . . ? C6 N1 Ni1 113.10(7) . . ? N1 C2 C3 121.88(12) . . ? N1 C2 C19 116.11(11) . . ? C3 C2 C19 122.00(11) . . ? C2 C3 C4 120.18(12) . . ? C5 C4 C3 118.72(12) . . ? C4 C5 C6 119.51(12) . . ? N1 C6 C5 121.67(11) . . ? N1 C6 C7 113.23(10) . . ? C5 C6 C7 125.07(11) . . ? N8 C7 C6 116.47(10) . . ? C7 N8 C9 116.47(10) . . ? C7 N8 Ni1 114.63(8) . . ? C9 N8 Ni1 128.90(8) . . ? N8 C9 C10 112.32(10) . . ? N11 C10 C9 112.16(10) . . ? C12 N11 C10 117.92(10) . . ? C12 N11 Ni2 114.72(8) . . ? C10 N11 Ni2 127.30(8) . . ? N11 C12 C13 116.09(10) . . ? N18 C13 C14 121.42(11) . . ? N18 C13 C12 113.06(10) . . ? C14 C13 C12 125.52(11) . . ? C15 C14 C13 119.05(11) . . ? C14 C15 C16 119.48(11) . . ? C17 C16 C15 119.69(12) . . ? N18 C17 C16 121.63(11) . . ? N18 C17 C20 116.28(9) . . ? C16 C17 C20 122.06(11) . . ? C17 N18 C13 118.64(10) . . ? C17 N18 Ni2 127.94(8) . . ? C13 N18 Ni2 113.41(8) . . ? C22 N21 C26 117.88(10) . . ? C22 N21 Ni1 129.08(7) . . ? C26 N21 Ni1 113.04(8) . . ? N21 C22 C23 122.39(11) . . ? N21 C22 C39 115.75(10) . . ? C23 C22 C39 121.84(11) . . ? C22 C23 C24 119.63(12) . . ? C25 C24 C23 118.93(11) . . ? C24 C25 C26 119.61(11) . . ? N21 C26 C25 121.53(11) . . ? N21 C26 C27 113.16(10) . . ? C25 C26 C27 125.31(11) . . ? N28 C27 C26 116.12(10) . . ? C27 N28 C29 117.29(10) . . ? C27 N28 Ni1 115.07(8) . . ? C29 N28 Ni1 127.50(8) . . ? N28 C29 C30 112.16(9) . . ? N31 C30 C29 112.93(10) . . ? C32 N31 C30 116.42(10) . . ? C32 N31 Ni2 114.58(8) . . ? C30 N31 Ni2 129.00(8) . . ? N31 C32 C33 116.37(10) . . ? N38 C33 C34 121.79(10) . . ? N38 C33 C32 113.30(10) . . ? C34 C33 C32 124.91(11) . . ? C35 C34 C33 119.47(11) . . ? C34 C35 C36 118.61(11) . . ? C37 C36 C35 120.16(11) . . ? N38 C37 C36 121.89(11) . . ? N38 C37 C40 115.70(10) . . ? C36 C37 C40 122.41(10) . . ? C37 N38 C33 118.08(10) . . ? C37 N38 Ni2 128.97(8) . . ? C33 N38 Ni2 112.93(7) . . ? O43 C42 C41 109.0(2) . . ? C42 O43 C44 113.1(3) . . ? O43 C44 C45 108.9(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 32.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.508 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.067 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 735553' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Cl4 N4 Zn2, 2 (C2 H3 N)' _chemical_formula_sum 'C20 H24 Cl4 N6 Zn2' _chemical_formula_weight 620.99 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3895(6) _cell_length_b 9.3625(8) _cell_length_c 9.7615(8) _cell_angle_alpha 108.0330(10) _cell_angle_beta 91.8910(10) _cell_angle_gamma 93.1840(10) _cell_volume 640.28(9) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9939 _cell_measurement_theta_min 3.44 _cell_measurement_theta_max 36.24 _exptl_crystal_description 'transparent block' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 314 _exptl_absorpt_coefficient_mu 2.311 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details SADABS _exptl_special_details ; SADABS Vers. 2006/1 , Bruker AXS (2006) ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode, 50 kV, 40 mA, INCOATEC Multi-Layer-Optics' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23460 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 34.99 _reflns_number_total 5597 _reflns_number_gt 5021 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT 7.34A, Bruker AXS' _computing_cell_refinement 'SAINT 7.34A, Bruker AXS' _computing_data_reduction 'SAINT 7.34A, Bruker AXS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.0806P] 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 5597 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0229 _refine_ls_wR_factor_ref 0.0629 _refine_ls_wR_factor_gt 0.0609 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 Zn1 Zn 0.197406(14) 0.269778(13) 0.268690(11) 0.01243(3) Uani 1 1 d . . . N1 N -0.00050(10) 0.19686(9) 0.38129(9) 0.01253(13) Uani 1 1 d . . . C2 C -0.12173(12) 0.07844(11) 0.33268(11) 0.01420(15) Uani 1 1 d . . . C3 C -0.23296(13) 0.03513(11) 0.42870(12) 0.01643(16) Uani 1 1 d . . . H3 H -0.3187 -0.0490 0.3937 0.020 Uiso 1 1 calc R . . C4 C -0.21785(13) 0.11478(12) 0.57404(12) 0.01679(17) Uani 1 1 d . . . H4 H -0.2919 0.0853 0.6397 0.020 Uiso 1 1 calc R . . C5 C -0.09211(13) 0.23951(11) 0.62354(11) 0.01501(16) Uani 1 1 d . . . H5 H -0.0802 0.2973 0.7227 0.018 Uiso 1 1 calc R . . C6 C 0.01391(12) 0.27576(10) 0.52386(10) 0.01225(14) Uani 1 1 d . . . C7 C 0.15683(12) 0.39966(11) 0.56761(10) 0.01339(15) Uani 1 1 d . . . H7 H 0.1707 0.4634 0.6648 0.016 Uiso 1 1 calc R . . N8 N 0.26184(10) 0.42012(9) 0.47297(9) 0.01290(13) Uani 1 1 d . . . C9 C 0.41023(12) 0.53724(11) 0.51645(11) 0.01508(16) Uani 1 1 d . . . H9A H 0.4080 0.5918 0.6209 0.018 Uiso 1 1 calc R . . H9B H 0.3969 0.6105 0.4628 0.018 Uiso 1 1 calc R . . C10 C -0.13194(15) -0.00539(13) 0.17459(11) 0.02041(19) Uani 1 1 d . . . H10A H -0.2110 0.0446 0.1239 0.031 Uiso 1 1 calc R . . H10B H -0.1814 -0.1089 0.1586 0.031 Uiso 1 1 calc R . . H10C H -0.0101 -0.0068 0.1377 0.031 Uiso 1 1 calc R . . Cl11 Cl 0.10308(4) 0.38321(3) 0.11549(3) 0.01927(5) Uani 1 1 d . . . Cl21 Cl 0.40149(3) 0.10082(3) 0.20253(3) 0.01845(5) Uani 1 1 d . . . N31 N -0.55476(16) 0.32419(14) 0.76187(13) 0.0304(2) Uani 1 1 d . . . C32 C -0.47440(15) 0.31827(13) 0.86169(12) 0.01989(18) Uani 1 1 d . . . C33 C -0.37030(19) 0.30908(15) 0.98685(13) 0.0268(2) Uani 1 1 d . . . H33A H -0.3254 0.2084 0.9661 0.040 Uiso 1 1 calc R . . H33B H -0.4478 0.3280 1.0693 0.040 Uiso 1 1 calc R . . H33C H -0.2673 0.3846 1.0098 0.040 Uiso 1 1 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 Zn1 0.01153(5) 0.01365(6) 0.01235(5) 0.00443(4) 0.00171(3) 0.00000(3) N1 0.0107(3) 0.0130(3) 0.0140(3) 0.0044(3) 0.0015(2) -0.0001(2) C2 0.0113(3) 0.0136(4) 0.0171(4) 0.0040(3) 0.0013(3) 0.0001(3) C3 0.0126(4) 0.0143(4) 0.0228(4) 0.0065(3) 0.0032(3) -0.0006(3) C4 0.0149(4) 0.0159(4) 0.0218(4) 0.0086(4) 0.0064(3) 0.0014(3) C5 0.0151(4) 0.0150(4) 0.0158(4) 0.0055(3) 0.0045(3) 0.0018(3) C6 0.0118(3) 0.0113(4) 0.0142(4) 0.0043(3) 0.0024(3) 0.0016(3) C7 0.0129(3) 0.0122(4) 0.0145(4) 0.0034(3) 0.0008(3) 0.0010(3) N8 0.0103(3) 0.0125(3) 0.0159(3) 0.0049(3) -0.0002(2) -0.0007(2) C9 0.0111(3) 0.0126(4) 0.0205(4) 0.0042(3) 0.0002(3) -0.0016(3) C10 0.0189(4) 0.0211(5) 0.0168(4) 0.0004(4) 0.0008(3) -0.0036(3) Cl11 0.02474(11) 0.01745(11) 0.01720(10) 0.00775(8) -0.00090(8) 0.00225(8) Cl21 0.01709(10) 0.01804(11) 0.02191(11) 0.00750(9) 0.00647(8) 0.00505(8) N31 0.0294(5) 0.0324(6) 0.0296(5) 0.0104(4) -0.0021(4) 0.0030(4) C32 0.0207(4) 0.0172(4) 0.0211(5) 0.0048(4) 0.0038(3) 0.0009(3) C33 0.0363(6) 0.0227(5) 0.0214(5) 0.0082(4) -0.0046(4) -0.0007(4) _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 Zn1 N1 2.0670(8) . ? Zn1 N8 2.0759(9) . ? Zn1 Cl11 2.2016(3) . ? Zn1 Cl21 2.2115(3) . ? N1 C2 1.3390(12) . ? N1 C6 1.3561(12) . ? C2 C3 1.4027(13) . ? C2 C10 1.4963(14) . ? C3 C4 1.3809(15) . ? C4 C5 1.4003(14) . ? C5 C6 1.3787(13) . ? C6 C7 1.4733(13) . ? C7 N8 1.2778(12) . ? N8 C9 1.4603(12) . ? C9 C9 1.5303(19) 2_666 ? N31 C32 1.1420(16) . ? C32 C33 1.4499(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn1 N8 80.77(3) . . ? N1 Zn1 Cl11 116.27(2) . . ? N8 Zn1 Cl11 112.20(2) . . ? N1 Zn1 Cl21 110.37(2) . . ? N8 Zn1 Cl21 111.79(2) . . ? Cl11 Zn1 Cl21 119.210(11) . . ? C2 N1 C6 119.80(8) . . ? C2 N1 Zn1 128.11(7) . . ? C6 N1 Zn1 111.78(6) . . ? N1 C2 C3 120.29(9) . . ? N1 C2 C10 117.80(8) . . ? C3 C2 C10 121.90(9) . . ? C4 C3 C2 120.01(9) . . ? C3 C4 C5 119.24(9) . . ? C6 C5 C4 117.93(9) . . ? N1 C6 C5 122.71(9) . . ? N1 C6 C7 115.69(8) . . ? C5 C6 C7 121.54(9) . . ? N8 C7 C6 119.03(9) . . ? C7 N8 C9 119.57(8) . . ? C7 N8 Zn1 112.64(7) . . ? C9 N8 Zn1 127.76(6) . . ? N8 C9 C9 108.50(10) . 2_666 ? N31 C32 C33 179.03(13) . . ? 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 N8 Zn1 N1 C2 -175.30(8) . . . . ? Cl11 Zn1 N1 C2 74.41(8) . . . . ? Cl21 Zn1 N1 C2 -65.38(8) . . . . ? N8 Zn1 N1 C6 -1.85(6) . . . . ? Cl11 Zn1 N1 C6 -112.14(6) . . . . ? Cl21 Zn1 N1 C6 108.07(6) . . . . ? C6 N1 C2 C3 -0.41(13) . . . . ? Zn1 N1 C2 C3 172.58(7) . . . . ? C6 N1 C2 C10 -179.74(9) . . . . ? Zn1 N1 C2 C10 -6.75(13) . . . . ? N1 C2 C3 C4 0.06(14) . . . . ? C10 C2 C3 C4 179.36(9) . . . . ? C2 C3 C4 C5 0.67(15) . . . . ? C3 C4 C5 C6 -1.03(14) . . . . ? C2 N1 C6 C5 0.02(14) . . . . ? Zn1 N1 C6 C5 -174.04(7) . . . . ? C2 N1 C6 C7 177.30(8) . . . . ? Zn1 N1 C6 C7 3.23(10) . . . . ? C4 C5 C6 N1 0.70(14) . . . . ? C4 C5 C6 C7 -176.41(9) . . . . ? N1 C6 C7 N8 -3.47(13) . . . . ? C5 C6 C7 N8 173.84(9) . . . . ? C6 C7 N8 C9 -176.68(8) . . . . ? C6 C7 N8 Zn1 1.73(11) . . . . ? N1 Zn1 N8 C7 0.04(7) . . . . ? Cl11 Zn1 N8 C7 114.74(6) . . . . ? Cl21 Zn1 N8 C7 -108.30(6) . . . . ? N1 Zn1 N8 C9 178.29(8) . . . . ? Cl11 Zn1 N8 C9 -67.00(8) . . . . ? Cl21 Zn1 N8 C9 69.95(8) . . . . ? C7 N8 C9 C9 118.53(11) . . . 2_666 ? Zn1 N8 C9 C9 -59.61(13) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 34.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.992 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.081 #===END