Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dr Gregory Solan' _publ_contact_author_address ; Department of Chemistry University of Leicester University Road Leicester Leicestershire LE1 7RH UNITED KINGDOM ; _publ_contact_author_email GAS8@LEICESTER.AC.UK _publ_section_title ; Substituted N-picolylethylenediamines of the type (ArNHCH2CH2){(2-C5H4N)CH2}NR [R = Me, 4-CH2=CH(C6H4)CH2, (2-C5H4N)CH2] and their Transition Metal(II) Halide complexes ; loop_ _publ_author_name 'Gregory Solan' 'Christopher J. Davies' 'John Fawcett' 'Richard Shutt' data_2136 _database_code_depnum_ccdc_archive 'CCDC 270047' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C22 H26 Cl2 N4 Mn) (C2 H3 N)' _chemical_formula_sum 'C24 H29 Cl2 Mn N5' _chemical_formula_weight 513.36 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' Mn Mn 0.3368 0.7283 '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 19.337(3) _cell_length_b 14.843(2) _cell_length_c 17.351(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.618(3) _cell_angle_gamma 90.00 _cell_volume 4910.0(13) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4366 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 27.01 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2136 _exptl_absorpt_coefficient_mu 0.777 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.747 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details ; absorption correction based on 4366 reflections (SADABS); Rint 0.053 before correction and 0.047 after. ; _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34315 _diffrn_reflns_av_R_equivalents 0.0788 _diffrn_reflns_av_sigmaI/netI 0.0906 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8554 _reflns_number_gt 6288 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1129P)^2^+35.5527P] 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 0.0032(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8554 _refine_ls_number_parameters 584 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1256 _refine_ls_R_factor_gt 0.1020 _refine_ls_wR_factor_ref 0.2695 _refine_ls_wR_factor_gt 0.2577 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.004 _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 Mn1 Mn 0.47692(6) 0.22159(8) 0.06201(7) 0.0211(3) Uani 1 1 d . . . Cl1 Cl 0.53122(11) 0.26032(15) 0.19244(12) 0.0334(5) Uani 1 1 d . . . Cl2 Cl 0.55980(10) 0.10884(13) 0.02542(12) 0.0277(5) Uani 1 1 d . . . N1 N 0.5196(3) 0.3309(4) -0.0088(4) 0.0250(15) Uani 1 1 d . . . N2 N 0.4093(3) 0.2236(4) -0.0634(4) 0.0244(15) Uani 1 1 d . . . N3 N 0.3782(3) 0.3008(4) 0.0736(4) 0.0248(15) Uani 1 1 d . . . N4 N 0.3971(3) 0.0976(4) 0.0613(4) 0.0232(14) Uani 1 1 d . . . H4' H 0.4245 0.0473 0.0556 0.028 Uiso 1 1 calc R . . C1 C 0.5629(4) 0.3975(5) 0.0210(5) 0.0298(19) Uani 1 1 d . . . H1 H 0.5754 0.4019 0.0762 0.036 Uiso 1 1 calc R . . C2 C 0.5900(5) 0.4598(6) -0.0246(6) 0.039(2) Uani 1 1 d . . . H2 H 0.6219 0.5047 -0.0014 0.047 Uiso 1 1 calc R . . C3 C 0.5701(5) 0.4557(6) -0.1040(6) 0.044(2) Uani 1 1 d . . . H3 H 0.5863 0.4992 -0.1370 0.053 Uiso 1 1 calc R . . C4 C 0.5267(5) 0.3881(6) -0.1345(5) 0.037(2) Uani 1 1 d . . . H4 H 0.5130 0.3836 -0.1895 0.044 Uiso 1 1 calc R . . C5 C 0.5024(4) 0.3259(5) -0.0862(5) 0.0242(17) Uani 1 1 d . . . C6 C 0.4569(5) 0.2480(6) -0.1185(5) 0.0297(19) Uani 1 1 d . . . H6A H 0.4291 0.2647 -0.1697 0.036 Uiso 1 1 calc R . . H6B H 0.4867 0.1956 -0.1265 0.036 Uiso 1 1 calc R . . C7 C 0.3528(5) 0.2908(6) -0.0684(5) 0.0301(19) Uani 1 1 d . . . H7A H 0.3114 0.2681 -0.1045 0.036 Uiso 1 1 calc R . . H7B H 0.3684 0.3470 -0.0910 0.036 Uiso 1 1 calc R . . C8 C 0.3312(5) 0.3125(5) 0.0091(5) 0.0290(19) Uani 1 1 d . . . C9 C 0.2652(5) 0.3479(6) 0.0112(6) 0.038(2) Uani 1 1 d . . . H9 H 0.2323 0.3549 -0.0355 0.046 Uiso 1 1 calc R . . C10 C 0.2480(6) 0.3727(7) 0.0822(7) 0.049(3) Uani 1 1 d . . . H10 H 0.2030 0.3970 0.0849 0.059 Uiso 1 1 calc R . . C11 C 0.2969(5) 0.3619(6) 0.1495(6) 0.044(3) Uani 1 1 d . . . H11 H 0.2867 0.3797 0.1990 0.053 Uiso 1 1 calc R . . C12 C 0.3609(5) 0.3244(6) 0.1424(5) 0.036(2) Uani 1 1 d . . . H12 H 0.3942 0.3150 0.1886 0.043 Uiso 1 1 calc R . . C13 C 0.3816(4) 0.1309(5) -0.0781(5) 0.0264(18) Uani 1 1 d . . . H13A H 0.4206 0.0894 -0.0833 0.032 Uiso 1 1 calc R . . H13B H 0.3479 0.1296 -0.1278 0.032 Uiso 1 1 calc R . . C14 C 0.3455(4) 0.0994(6) -0.0120(5) 0.0278(18) Uani 1 1 d . . . H14A H 0.3065 0.1409 -0.0063 0.033 Uiso 1 1 calc R . . H14B H 0.3257 0.0385 -0.0236 0.033 Uiso 1 1 calc R . . C15 C 0.3673(4) 0.0780(5) 0.1303(4) 0.0205(16) Uani 1 1 d . . . C16 C 0.4054(4) 0.0231(5) 0.1888(4) 0.0242(17) Uani 1 1 d . . . C17 C 0.3743(4) -0.0010(6) 0.2531(5) 0.0293(19) Uani 1 1 d . . . H17 H 0.3991 -0.0392 0.2922 0.035 Uiso 1 1 calc R . . C18 C 0.3072(5) 0.0301(6) 0.2614(5) 0.0297(19) Uani 1 1 d . . . C19 C 0.2732(5) 0.0881(6) 0.2057(5) 0.033(2) Uani 1 1 d . . . H19 H 0.2290 0.1125 0.2121 0.039 Uiso 1 1 calc R . . C20 C 0.3022(4) 0.1120(6) 0.1399(5) 0.0296(19) Uani 1 1 d . . . H20 H 0.2775 0.1514 0.1018 0.035 Uiso 1 1 calc R . . C21 C 0.4754(5) -0.0127(6) 0.1822(5) 0.034(2) Uani 1 1 d . . . H21A H 0.4943 -0.0461 0.2299 0.051 Uiso 1 1 calc R . . H21B H 0.5070 0.0373 0.1754 0.051 Uiso 1 1 calc R . . H21C H 0.4715 -0.0531 0.1371 0.051 Uiso 1 1 calc R . . C22 C 0.2729(5) -0.0044(8) 0.3282(6) 0.048(3) Uani 1 1 d . . . H22A H 0.2488 0.0453 0.3497 0.071 Uiso 1 1 calc R . . H22B H 0.3088 -0.0295 0.3691 0.071 Uiso 1 1 calc R . . H22C H 0.2388 -0.0515 0.3088 0.071 Uiso 1 1 calc R . . Mn1A Mn 0.13988(6) 0.67957(8) 0.23263(7) 0.0232(3) Uani 1 1 d . . . Cl1A Cl 0.03219(11) 0.75215(15) 0.18456(13) 0.0345(5) Uani 1 1 d . . . Cl2A Cl 0.13450(11) 0.54206(14) 0.14580(12) 0.0316(5) Uani 1 1 d . . . N1A N 0.2114(4) 0.7593(5) 0.1684(4) 0.0271(15) Uani 1 1 d . . . N2A N 0.2559(4) 0.6467(5) 0.2878(4) 0.0263(15) Uani 1 1 d . . . N3A N 0.1662(4) 0.7734(5) 0.3379(4) 0.0266(15) Uani 1 1 d . . . N4A N 0.1282(3) 0.5691(5) 0.3293(4) 0.0251(15) Uani 1 1 d . . . H4A' H 0.1175 0.5159 0.3016 0.030 Uiso 1 1 calc R . . C1A C 0.1924(5) 0.8358(6) 0.1277(5) 0.0299(19) Uani 1 1 d . . . H1A H 0.1454 0.8561 0.1237 0.036 Uiso 1 1 calc R . . C2A C 0.2385(5) 0.8860(6) 0.0918(5) 0.034(2) Uani 1 1 d . . . H2A H 0.2238 0.9397 0.0642 0.041 Uiso 1 1 calc R . . C3A C 0.3066(5) 0.8552(6) 0.0974(5) 0.033(2) Uani 1 1 d . . . H3A H 0.3392 0.8865 0.0720 0.040 Uiso 1 1 calc R . . C4A C 0.3266(5) 0.7791(6) 0.1400(5) 0.0293(19) Uani 1 1 d . . . H4A H 0.3737 0.7586 0.1461 0.035 Uiso 1 1 calc R . . C5A C 0.2779(4) 0.7327(6) 0.1739(5) 0.0286(19) Uani 1 1 d . . . C6A C 0.2953(4) 0.6473(6) 0.2216(5) 0.0269(18) Uani 1 1 d . . . H6A1 H 0.2824 0.5938 0.1881 0.032 Uiso 1 1 calc R . . H6A2 H 0.3463 0.6447 0.2416 0.032 Uiso 1 1 calc R . . C7A C 0.2846(4) 0.7158(6) 0.3454(5) 0.0285(19) Uani 1 1 d . . . H7A1 H 0.3120 0.7595 0.3197 0.034 Uiso 1 1 calc R . . H7A2 H 0.3172 0.6864 0.3880 0.034 Uiso 1 1 calc R . . C8A C 0.2300(4) 0.7665(5) 0.3807(5) 0.0258(18) Uani 1 1 d . . . C9A C 0.2481(5) 0.8080(6) 0.4529(5) 0.033(2) Uani 1 1 d . . . H9A H 0.2938 0.8010 0.4825 0.039 Uiso 1 1 calc R . . C10A C 0.1979(5) 0.8599(6) 0.4807(5) 0.038(2) Uani 1 1 d . . . H10A H 0.2087 0.8895 0.5298 0.046 Uiso 1 1 calc R . . C11A C 0.1323(6) 0.8679(6) 0.4361(6) 0.042(2) Uani 1 1 d . . . H11A H 0.0960 0.9018 0.4531 0.051 Uiso 1 1 calc R . . C12A C 0.1226(5) 0.8238(5) 0.3653(4) 0.0273(19) Uani 1 1 d . . . H12A H 0.0783 0.8319 0.3331 0.033 Uiso 1 1 calc R . . C13A C 0.2543(5) 0.5568(6) 0.3237(5) 0.033(2) Uani 1 1 d . . . H13C H 0.3009 0.5429 0.3545 0.039 Uiso 1 1 calc R . . H13D H 0.2435 0.5107 0.2822 0.039 Uiso 1 1 calc R . . C14A C 0.1990(4) 0.5537(6) 0.3768(5) 0.0271(18) Uani 1 1 d . . . H14C H 0.2002 0.4943 0.4029 0.033 Uiso 1 1 calc R . . H14D H 0.2090 0.6007 0.4176 0.033 Uiso 1 1 calc R . . C15A C 0.0712(4) 0.5822(6) 0.3732(5) 0.0282(19) Uani 1 1 d . . . C16A C 0.0047(4) 0.5470(6) 0.3417(5) 0.0298(19) Uani 1 1 d . . . C17A C -0.0501(5) 0.5626(6) 0.3836(5) 0.036(2) Uani 1 1 d . . . H17A H -0.0952 0.5393 0.3633 0.043 Uiso 1 1 calc R . . C18A C -0.0415(5) 0.6106(6) 0.4537(6) 0.036(2) Uani 1 1 d . . . C19A C 0.0242(4) 0.6440(6) 0.4808(5) 0.0292(19) Uani 1 1 d . . . H19A H 0.0315 0.6776 0.5281 0.035 Uiso 1 1 calc R . . C20A C 0.0793(5) 0.6307(6) 0.4423(5) 0.032(2) Uani 1 1 d . . . H20A H 0.1239 0.6550 0.4633 0.039 Uiso 1 1 calc R . . C21A C -0.0084(5) 0.4931(7) 0.2665(6) 0.046(3) Uani 1 1 d . . . H21D H 0.0266 0.4450 0.2689 0.069 Uiso 1 1 calc R . . H21E H -0.0049 0.5329 0.2222 0.069 Uiso 1 1 calc R . . H21F H -0.0555 0.4666 0.2598 0.069 Uiso 1 1 calc R . . C22A C -0.1032(6) 0.6244(7) 0.4971(6) 0.046(3) Uani 1 1 d . . . H22D H -0.1323 0.6743 0.4732 0.069 Uiso 1 1 calc R . . H22E H -0.0855 0.6384 0.5520 0.069 Uiso 1 1 calc R . . H22F H -0.1314 0.5692 0.4939 0.069 Uiso 1 1 calc R . . N5 N 0.7960(6) 0.8349(7) 0.1757(7) 0.065(3) Uani 1 1 d . . . C23 C 0.8371(6) 0.8099(7) 0.2251(7) 0.045(2) Uani 1 1 d . . . C24 C 0.8893(6) 0.7759(8) 0.2880(8) 0.063(3) Uani 1 1 d . . . H24A H 0.8664 0.7578 0.3319 0.095 Uiso 1 1 calc R . . H24B H 0.9238 0.8232 0.3051 0.095 Uiso 1 1 calc R . . H24C H 0.9129 0.7238 0.2695 0.095 Uiso 1 1 calc R . . N6 N 0.8737(6) 0.6154(8) 0.1290(7) 0.074(3) Uani 1 1 d . . . C25 C 0.9111(6) 0.6136(8) 0.0841(9) 0.063(4) Uani 1 1 d . . . C26 C 0.9615(7) 0.6137(8) 0.0314(8) 0.067(4) Uani 1 1 d . . . H26A H 0.9638 0.6740 0.0089 0.100 Uiso 1 1 calc R . . H26B H 0.9471 0.5701 -0.0106 0.100 Uiso 1 1 calc R . . H26C H 1.0077 0.5971 0.0601 0.100 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 Mn1 0.0245(7) 0.0213(6) 0.0179(6) 0.0002(5) 0.0049(5) -0.0006(5) Cl1 0.0362(12) 0.0427(13) 0.0204(10) -0.0061(9) 0.0021(9) -0.0011(10) Cl2 0.0275(10) 0.0261(10) 0.0307(11) -0.0039(8) 0.0079(8) 0.0017(8) N1 0.026(4) 0.025(4) 0.024(4) -0.004(3) 0.004(3) 0.003(3) N2 0.029(4) 0.017(3) 0.028(4) 0.006(3) 0.007(3) 0.002(3) N3 0.026(4) 0.023(4) 0.026(4) -0.004(3) 0.006(3) -0.003(3) N4 0.033(4) 0.017(3) 0.019(3) -0.001(3) 0.005(3) 0.002(3) C1 0.032(5) 0.021(4) 0.034(5) -0.004(4) 0.001(4) -0.004(4) C2 0.035(5) 0.026(5) 0.055(6) -0.001(4) 0.004(5) -0.005(4) C3 0.056(6) 0.030(5) 0.050(6) 0.009(4) 0.022(5) -0.006(4) C4 0.056(6) 0.026(5) 0.033(5) 0.003(4) 0.021(4) 0.001(4) C5 0.027(4) 0.023(4) 0.023(4) -0.001(3) 0.005(3) 0.013(3) C6 0.035(5) 0.028(5) 0.030(5) -0.005(4) 0.017(4) -0.005(4) C7 0.033(5) 0.028(5) 0.028(5) 0.005(4) 0.001(4) 0.003(4) C8 0.034(5) 0.016(4) 0.039(5) 0.007(4) 0.010(4) 0.001(3) C9 0.031(5) 0.037(5) 0.043(6) 0.007(4) -0.001(4) 0.003(4) C10 0.046(6) 0.041(6) 0.064(7) 0.000(5) 0.020(6) 0.021(5) C11 0.053(6) 0.029(5) 0.058(7) -0.011(5) 0.035(5) -0.001(4) C12 0.051(6) 0.027(5) 0.030(5) -0.001(4) 0.012(4) 0.004(4) C13 0.034(5) 0.020(4) 0.023(4) 0.002(3) -0.001(4) -0.002(3) C14 0.032(5) 0.024(4) 0.026(4) 0.000(3) 0.001(4) -0.004(3) C15 0.025(4) 0.018(4) 0.019(4) -0.004(3) 0.006(3) -0.006(3) C16 0.029(4) 0.024(4) 0.019(4) -0.001(3) 0.001(3) 0.000(3) C17 0.031(5) 0.033(5) 0.025(4) 0.001(4) 0.007(4) 0.002(4) C18 0.042(5) 0.025(4) 0.024(4) -0.004(3) 0.012(4) -0.001(4) C19 0.033(5) 0.033(5) 0.037(5) -0.003(4) 0.016(4) 0.004(4) C20 0.029(5) 0.029(5) 0.031(5) 0.001(4) 0.008(4) 0.000(4) C21 0.034(5) 0.040(5) 0.028(5) 0.003(4) 0.005(4) 0.009(4) C22 0.046(6) 0.059(7) 0.038(6) -0.001(5) 0.009(5) -0.012(5) Mn1A 0.0227(7) 0.0259(7) 0.0213(6) 0.0007(5) 0.0049(5) 0.0014(5) Cl1A 0.0293(11) 0.0383(12) 0.0347(12) 0.0000(9) 0.0019(9) 0.0066(9) Cl2A 0.0382(12) 0.0307(11) 0.0270(11) -0.0044(9) 0.0088(9) 0.0005(9) N1A 0.026(4) 0.028(4) 0.027(4) 0.005(3) 0.003(3) 0.001(3) N2A 0.030(4) 0.029(4) 0.019(3) 0.002(3) 0.002(3) 0.002(3) N3A 0.030(4) 0.027(4) 0.024(4) -0.002(3) 0.006(3) 0.003(3) N4A 0.024(4) 0.028(4) 0.024(4) -0.001(3) 0.005(3) 0.001(3) C1A 0.029(5) 0.036(5) 0.023(4) 0.003(4) 0.000(4) 0.002(4) C2A 0.050(6) 0.030(5) 0.023(4) 0.002(4) 0.006(4) -0.005(4) C3A 0.038(5) 0.025(4) 0.040(5) -0.002(4) 0.013(4) -0.012(4) C4A 0.034(5) 0.033(5) 0.022(4) -0.001(4) 0.007(4) -0.008(4) C5A 0.029(5) 0.034(5) 0.023(4) -0.006(4) 0.002(4) 0.001(4) C6A 0.028(4) 0.027(4) 0.027(4) 0.005(3) 0.006(4) 0.006(3) C7A 0.023(4) 0.038(5) 0.024(4) 0.001(4) 0.003(3) -0.003(4) C8A 0.029(5) 0.023(4) 0.024(4) 0.007(3) 0.002(3) -0.002(3) C9A 0.040(5) 0.035(5) 0.023(4) -0.003(4) 0.005(4) -0.014(4) C10A 0.053(6) 0.035(5) 0.026(5) -0.003(4) 0.007(4) -0.005(4) C11A 0.057(7) 0.033(5) 0.042(6) -0.005(4) 0.026(5) 0.010(5) C12A 0.046(5) 0.017(4) 0.017(4) 0.006(3) 0.000(4) 0.000(4) C13A 0.031(5) 0.031(5) 0.037(5) 0.005(4) 0.005(4) 0.003(4) C14A 0.031(5) 0.021(4) 0.031(5) 0.005(3) 0.010(4) 0.005(3) C15A 0.030(5) 0.025(4) 0.032(5) 0.002(4) 0.012(4) -0.003(3) C16A 0.031(5) 0.028(5) 0.030(5) 0.002(4) 0.007(4) -0.005(4) C17A 0.031(5) 0.034(5) 0.042(6) 0.010(4) 0.002(4) 0.000(4) C18A 0.035(5) 0.030(5) 0.046(6) 0.006(4) 0.014(4) 0.003(4) C19A 0.034(5) 0.031(5) 0.023(4) 0.001(4) 0.006(4) 0.002(4) C20A 0.026(5) 0.040(5) 0.031(5) -0.004(4) 0.004(4) -0.002(4) C21A 0.038(6) 0.038(6) 0.062(7) -0.010(5) 0.005(5) -0.004(4) C22A 0.057(7) 0.038(6) 0.049(6) -0.002(5) 0.024(5) -0.002(5) N5 0.067(7) 0.056(6) 0.072(7) 0.006(5) 0.008(6) 0.002(5) C23 0.045(6) 0.037(6) 0.057(7) 0.007(5) 0.021(5) 0.003(5) C24 0.044(7) 0.066(8) 0.083(9) 0.030(7) 0.024(6) 0.006(6) N6 0.054(7) 0.069(8) 0.093(9) -0.003(7) -0.005(6) -0.008(6) C25 0.036(7) 0.049(7) 0.095(11) -0.010(7) -0.014(7) 0.005(5) C26 0.065(8) 0.051(7) 0.075(9) -0.011(6) -0.016(7) 0.007(6) _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 Mn1 N1 2.272(7) . ? Mn1 N3 2.279(7) . ? Mn1 N2 2.344(7) . ? Mn1 Cl1 2.400(2) . ? Mn1 N4 2.400(6) . ? Mn1 Cl2 2.472(2) . ? N1 C5 1.332(10) . ? N1 C1 1.341(10) . ? N2 C7 1.472(10) . ? N2 C6 1.478(10) . ? N2 C13 1.484(10) . ? N3 C8 1.331(11) . ? N3 C12 1.340(11) . ? N4 C15 1.442(9) . ? N4 C14 1.480(10) . ? C1 C2 1.377(13) . ? C2 C3 1.369(14) . ? C3 C4 1.357(13) . ? C4 C5 1.380(12) . ? C5 C6 1.505(11) . ? C7 C8 1.508(12) . ? C8 C9 1.386(12) . ? C9 C10 1.378(14) . ? C10 C11 1.383(15) . ? C11 C12 1.381(13) . ? C13 C14 1.512(11) . ? C15 C20 1.392(11) . ? C15 C16 1.410(11) . ? C16 C17 1.400(11) . ? C16 C21 1.477(12) . ? C17 C18 1.405(12) . ? C18 C19 1.378(12) . ? C18 C22 1.518(12) . ? C19 C20 1.400(12) . ? Mn1A N1A 2.252(7) . ? Mn1A N3A 2.285(7) . ? Mn1A N2A 2.340(7) . ? Mn1A Cl1A 2.369(2) . ? Mn1A N4A 2.383(7) . ? Mn1A Cl2A 2.529(2) . ? N1A C5A 1.333(11) . ? N1A C1A 1.355(11) . ? N2A C7A 1.474(10) . ? N2A C13A 1.474(11) . ? N2A C6A 1.481(10) . ? N3A C12A 1.277(11) . ? N3A C8A 1.333(10) . ? N4A C15A 1.454(10) . ? N4A C14A 1.492(10) . ? C1A C2A 1.386(12) . ? C2A C3A 1.381(13) . ? C3A C4A 1.369(12) . ? C4A C5A 1.375(12) . ? C5A C6A 1.520(11) . ? C7A C8A 1.506(12) . ? C8A C9A 1.388(12) . ? C9A C10A 1.388(13) . ? C10A C11A 1.377(14) . ? C11A C12A 1.376(12) . ? C13A C14A 1.525(11) . ? C15A C20A 1.385(12) . ? C15A C16A 1.410(12) . ? C16A C17A 1.400(12) . ? C16A C21A 1.516(13) . ? C17A C18A 1.396(13) . ? C18A C19A 1.372(13) . ? C18A C22A 1.526(13) . ? C19A C20A 1.363(12) . ? N5 C23 1.129(14) . ? C23 C24 1.447(16) . ? N6 C25 1.148(17) . ? C25 C26 1.444(19) . ? 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 Mn1 N3 93.7(2) . . ? N1 Mn1 N2 71.7(2) . . ? N3 Mn1 N2 74.4(2) . . ? N1 Mn1 Cl1 101.38(18) . . ? N3 Mn1 Cl1 91.95(18) . . ? N2 Mn1 Cl1 163.86(17) . . ? N1 Mn1 N4 146.7(2) . . ? N3 Mn1 N4 81.3(2) . . ? N2 Mn1 N4 75.3(2) . . ? Cl1 Mn1 N4 111.61(16) . . ? N1 Mn1 Cl2 92.01(17) . . ? N3 Mn1 Cl2 163.80(18) . . ? N2 Mn1 Cl2 93.15(17) . . ? Cl1 Mn1 Cl2 101.77(8) . . ? N4 Mn1 Cl2 85.62(17) . . ? C5 N1 C1 117.7(7) . . ? C5 N1 Mn1 117.0(5) . . ? C1 N1 Mn1 125.3(6) . . ? C7 N2 C6 109.4(6) . . ? C7 N2 C13 112.0(6) . . ? C6 N2 C13 111.2(6) . . ? C7 N2 Mn1 110.9(5) . . ? C6 N2 Mn1 107.1(5) . . ? C13 N2 Mn1 106.1(4) . . ? C8 N3 C12 118.5(7) . . ? C8 N3 Mn1 117.3(5) . . ? C12 N3 Mn1 123.5(6) . . ? C15 N4 C14 114.3(6) . . ? C15 N4 Mn1 119.7(4) . . ? C14 N4 Mn1 109.4(5) . . ? N1 C1 C2 123.1(8) . . ? C3 C2 C1 118.6(9) . . ? C4 C3 C2 118.4(9) . . ? C3 C4 C5 120.6(9) . . ? N1 C5 C4 121.5(8) . . ? N1 C5 C6 116.8(7) . . ? C4 C5 C6 121.7(8) . . ? N2 C6 C5 109.6(6) . . ? N2 C7 C8 114.0(7) . . ? N3 C8 C9 122.0(8) . . ? N3 C8 C7 118.0(7) . . ? C9 C8 C7 119.9(8) . . ? C10 C9 C8 119.0(9) . . ? C9 C10 C11 119.4(9) . . ? C12 C11 C10 117.9(9) . . ? N3 C12 C11 123.1(9) . . ? N2 C13 C14 110.8(6) . . ? N4 C14 C13 109.0(7) . . ? C20 C15 C16 119.8(7) . . ? C20 C15 N4 121.4(7) . . ? C16 C15 N4 118.8(7) . . ? C17 C16 C15 118.6(7) . . ? C17 C16 C21 119.4(7) . . ? C15 C16 C21 121.9(7) . . ? C16 C17 C18 121.6(8) . . ? C19 C18 C17 118.4(8) . . ? C19 C18 C22 121.8(8) . . ? C17 C18 C22 119.8(8) . . ? C18 C19 C20 121.3(8) . . ? C15 C20 C19 120.0(8) . . ? N1A Mn1A N3A 90.1(3) . . ? N1A Mn1A N2A 71.7(2) . . ? N3A Mn1A N2A 74.3(2) . . ? N1A Mn1A Cl1A 99.40(18) . . ? N3A Mn1A Cl1A 93.98(18) . . ? N2A Mn1A Cl1A 164.94(19) . . ? N1A Mn1A N4A 148.0(2) . . ? N3A Mn1A N4A 83.8(2) . . ? N2A Mn1A N4A 76.4(2) . . ? Cl1A Mn1A N4A 112.32(17) . . ? N1A Mn1A Cl2A 95.54(19) . . ? N3A Mn1A Cl2A 161.72(19) . . ? N2A Mn1A Cl2A 90.95(18) . . ? Cl1A Mn1A Cl2A 102.18(9) . . ? N4A Mn1A Cl2A 82.23(17) . . ? C5A N1A C1A 117.4(7) . . ? C5A N1A Mn1A 118.2(6) . . ? C1A N1A Mn1A 124.2(6) . . ? C7A N2A C13A 112.1(7) . . ? C7A N2A C6A 109.8(6) . . ? C13A N2A C6A 112.5(6) . . ? C7A N2A Mn1A 111.0(5) . . ? C13A N2A Mn1A 106.0(5) . . ? C6A N2A Mn1A 105.2(5) . . ? C12A N3A C8A 116.4(7) . . ? C12A N3A Mn1A 125.6(6) . . ? C8A N3A Mn1A 117.4(5) . . ? C15A N4A C14A 115.9(6) . . ? C15A N4A Mn1A 116.5(5) . . ? C14A N4A Mn1A 108.0(5) . . ? N1A C1A C2A 123.0(8) . . ? C3A C2A C1A 117.9(8) . . ? C4A C3A C2A 119.4(8) . . ? C3A C4A C5A 119.5(8) . . ? N1A C5A C4A 122.8(8) . . ? N1A C5A C6A 114.1(7) . . ? C4A C5A C6A 123.1(8) . . ? N2A C6A C5A 109.4(6) . . ? N2A C7A C8A 114.4(7) . . ? N3A C8A C9A 122.7(8) . . ? N3A C8A C7A 117.3(7) . . ? C9A C8A C7A 120.0(7) . . ? C8A C9A C10A 118.3(9) . . ? C11A C10A C9A 119.0(8) . . ? C12A C11A C10A 115.9(9) . . ? N3A C12A C11A 127.7(9) . . ? N2A C13A C14A 110.4(7) . . ? N4A C14A C13A 109.4(7) . . ? C20A C15A C16A 119.4(8) . . ? C20A C15A N4A 122.5(7) . . ? C16A C15A N4A 118.0(7) . . ? C17A C16A C15A 117.3(8) . . ? C17A C16A C21A 120.0(8) . . ? C15A C16A C21A 122.7(8) . . ? C18A C17A C16A 123.1(8) . . ? C19A C18A C17A 116.8(8) . . ? C19A C18A C22A 122.5(9) . . ? C17A C18A C22A 120.6(9) . . ? C20A C19A C18A 122.3(8) . . ? C19A C20A C15A 121.0(8) . . ? N5 C23 C24 178.8(13) . . ? N6 C25 C26 176.4(14) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.973 _refine_diff_density_min -0.770 _refine_diff_density_rms 0.144 data_04063 _database_code_depnum_ccdc_archive 'CCDC 270048' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H25 Cl2 Co N3' _chemical_formula_weight 413.24 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' 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 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 15.410(3) _cell_length_b 7.4772(14) _cell_length_c 16.863(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.761(3) _cell_angle_gamma 90.00 _cell_volume 1936.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2291 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 24.35 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 1.167 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.57 _exptl_absorpt_correction_T_max 0.86 _exptl_absorpt_process_details ; absorption correction based on 4644 reflections(SADABS);Rint 0.063 before correction and 0.045 after. ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13964 _diffrn_reflns_av_R_equivalents 0.0809 _diffrn_reflns_av_sigmaI/netI 0.0855 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3785 _reflns_number_gt 2620 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0925P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3785 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.1751 _refine_ls_wR_factor_gt 0.1574 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.29507(5) 1.10022(9) 0.11153(4) 0.0230(2) Uani 1 1 d . . . Cl1 Cl 0.17287(9) 1.26852(17) 0.07353(8) 0.0304(4) Uani 1 1 d . . . Cl2 Cl 0.40918(9) 1.29182(18) 0.09110(9) 0.0328(4) Uani 1 1 d . . . N1 N 0.2775(3) 1.0839(6) 0.2330(3) 0.0287(11) Uani 1 1 d . . . N2 N 0.3917(3) 0.8900(6) 0.1566(3) 0.0284(10) Uani 1 1 d . . . N3 N 0.2333(3) 0.8615(5) 0.0600(3) 0.0254(10) Uani 1 1 d . . . H3A H 0.1869 0.8446 0.0911 0.030 Uiso 1 1 d R . . C1 C 0.2077(4) 1.1445(7) 0.2678(3) 0.0336(14) Uani 1 1 d . . . H1 H 0.1599 1.1906 0.2347 0.040 Uiso 1 1 calc R . . C2 C 0.2019(4) 1.1431(8) 0.3493(4) 0.0388(15) Uani 1 1 d . . . H2 H 0.1510 1.1844 0.3717 0.047 Uiso 1 1 calc R . . C3 C 0.2724(5) 1.0799(8) 0.3972(4) 0.0420(16) Uani 1 1 d . . . H3 H 0.2713 1.0811 0.4535 0.050 Uiso 1 1 calc R . . C4 C 0.3439(4) 1.0158(8) 0.3633(3) 0.0390(15) Uani 1 1 d . . . H4 H 0.3923 0.9709 0.3959 0.047 Uiso 1 1 calc R . . C5 C 0.3450(4) 1.0167(7) 0.2806(3) 0.0270(12) Uani 1 1 d . . . C6 C 0.4194(4) 0.9519(7) 0.2383(3) 0.0329(13) Uani 1 1 d . . . H6A H 0.4483 0.8521 0.2687 0.039 Uiso 1 1 calc R . . H6B H 0.4624 1.0497 0.2355 0.039 Uiso 1 1 calc R . . C7 C 0.4693(4) 0.8593(8) 0.1133(4) 0.0378(15) Uani 1 1 d . . . H7A H 0.4990 0.9734 0.1060 0.057 Uiso 1 1 calc R . . H7B H 0.4519 0.8067 0.0612 0.057 Uiso 1 1 calc R . . H7C H 0.5089 0.7774 0.1438 0.057 Uiso 1 1 calc R . . C8 C 0.3388(4) 0.7255(7) 0.1581(3) 0.0282(12) Uani 1 1 d . . . H8A H 0.2980 0.7350 0.2003 0.034 Uiso 1 1 calc R . . H8B H 0.3772 0.6213 0.1703 0.034 Uiso 1 1 calc R . . C9 C 0.2877(4) 0.6984(7) 0.0780(3) 0.0291(13) Uani 1 1 d . . . H9A H 0.3282 0.6800 0.0361 0.035 Uiso 1 1 calc R . . H9B H 0.2500 0.5915 0.0798 0.035 Uiso 1 1 calc R . . C10 C 0.1906(3) 0.8591(7) -0.0214(3) 0.0249(12) Uani 1 1 d . . . C11 C 0.1032(4) 0.8073(8) -0.0315(3) 0.0313(13) Uani 1 1 d . . . C12 C 0.0626(4) 0.8021(8) -0.1092(3) 0.0342(14) Uani 1 1 d . . . H12 H 0.0035 0.7652 -0.1174 0.041 Uiso 1 1 calc R . . C13 C 0.1071(4) 0.8498(8) -0.1741(3) 0.0368(14) Uani 1 1 d . . . C14 C 0.1930(4) 0.9003(8) -0.1616(3) 0.0372(15) Uani 1 1 d . . . H14 H 0.2237 0.9329 -0.2060 0.045 Uiso 1 1 calc R . . C15 C 0.2364(4) 0.9051(7) -0.0856(3) 0.0286(12) Uani 1 1 d . . . C16 C 0.0522(4) 0.7572(9) 0.0373(3) 0.0413(16) Uani 1 1 d . . . H16A H 0.0769 0.6486 0.0626 0.062 Uiso 1 1 calc R . . H16B H -0.0086 0.7355 0.0180 0.062 Uiso 1 1 calc R . . H16C H 0.0550 0.8550 0.0761 0.062 Uiso 1 1 calc R . . C17 C 0.0629(5) 0.8452(11) -0.2575(4) 0.061(2) Uani 1 1 d . . . H17A H 0.0887 0.9364 -0.2900 0.091 Uiso 1 1 calc R . . H17B H 0.0006 0.8694 -0.2556 0.091 Uiso 1 1 calc R . . H17C H 0.0708 0.7269 -0.2808 0.091 Uiso 1 1 calc R . . C18 C 0.3300(4) 0.9642(8) -0.0776(4) 0.0364(14) Uani 1 1 d . . . H18A H 0.3404 1.0396 -0.0302 0.055 Uiso 1 1 calc R . . H18B H 0.3425 1.0325 -0.1249 0.055 Uiso 1 1 calc R . . H18C H 0.3679 0.8590 -0.0724 0.055 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 Co1 0.0279(4) 0.0196(4) 0.0209(4) 0.0002(3) -0.0004(3) -0.0006(3) Cl1 0.0299(7) 0.0261(7) 0.0344(8) 0.0033(6) -0.0013(6) 0.0023(6) Cl2 0.0323(8) 0.0245(7) 0.0412(9) 0.0004(6) 0.0016(6) -0.0055(6) N1 0.033(3) 0.029(3) 0.024(2) -0.0057(19) 0.002(2) -0.005(2) N2 0.028(2) 0.024(2) 0.034(3) 0.000(2) 0.007(2) 0.001(2) N3 0.027(2) 0.025(2) 0.024(2) 0.0005(18) 0.0016(19) 0.0022(19) C1 0.043(4) 0.029(3) 0.028(3) -0.001(2) 0.005(3) 0.004(3) C2 0.056(4) 0.032(3) 0.030(3) 0.001(3) 0.015(3) 0.001(3) C3 0.076(5) 0.028(3) 0.022(3) 0.000(2) 0.006(3) -0.006(3) C4 0.060(4) 0.028(3) 0.027(3) 0.003(3) -0.005(3) -0.007(3) C5 0.039(3) 0.021(3) 0.020(3) 0.000(2) -0.004(2) -0.006(3) C6 0.034(3) 0.027(3) 0.036(3) 0.002(2) -0.004(3) 0.000(3) C7 0.029(3) 0.035(3) 0.050(4) 0.002(3) 0.005(3) 0.006(3) C8 0.034(3) 0.022(3) 0.028(3) -0.002(2) -0.003(2) -0.002(2) C9 0.043(3) 0.016(3) 0.027(3) -0.003(2) -0.003(3) 0.008(3) C10 0.032(3) 0.026(3) 0.016(3) -0.007(2) -0.002(2) -0.001(2) C11 0.035(3) 0.032(3) 0.027(3) -0.002(2) 0.002(2) -0.002(3) C12 0.034(3) 0.047(4) 0.021(3) -0.003(3) 0.002(2) -0.008(3) C13 0.047(4) 0.041(3) 0.023(3) -0.007(3) 0.006(3) -0.002(3) C14 0.057(4) 0.035(3) 0.023(3) -0.002(2) 0.019(3) -0.001(3) C15 0.036(3) 0.024(3) 0.025(3) -0.005(2) 0.003(2) -0.002(3) C16 0.028(3) 0.070(5) 0.026(3) 0.003(3) -0.001(3) -0.011(3) C17 0.069(5) 0.087(6) 0.025(4) -0.003(4) -0.008(3) -0.020(4) C18 0.042(4) 0.034(3) 0.034(3) -0.001(3) 0.010(3) -0.004(3) _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 N1 2.093(4) . ? Co1 N3 2.170(4) . ? Co1 N2 2.254(4) . ? Co1 Cl1 2.3107(15) . ? Co1 Cl2 2.3159(15) . ? N1 C1 1.345(7) . ? N1 C5 1.357(7) . ? N2 C7 1.470(7) . ? N2 C8 1.478(7) . ? N2 C6 1.482(7) . ? N3 C10 1.472(6) . ? N3 C9 1.497(6) . ? C1 C2 1.385(8) . ? C2 C3 1.382(9) . ? C3 C4 1.369(9) . ? C4 C5 1.397(7) . ? C5 C6 1.481(8) . ? C8 C9 1.519(7) . ? C10 C15 1.384(7) . ? C10 C11 1.398(7) . ? C11 C12 1.405(8) . ? C11 C16 1.501(7) . ? C12 C13 1.385(8) . ? C13 C14 1.376(8) . ? C13 C17 1.511(8) . ? C14 C15 1.396(8) . ? C15 C18 1.503(8) . ? 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 Co1 N3 104.82(16) . . ? N1 Co1 N2 76.42(17) . . ? N3 Co1 N2 79.45(16) . . ? N1 Co1 Cl1 97.73(13) . . ? N3 Co1 Cl1 90.95(12) . . ? N2 Co1 Cl1 166.88(12) . . ? N1 Co1 Cl2 110.09(13) . . ? N3 Co1 Cl2 139.68(12) . . ? N2 Co1 Cl2 89.59(12) . . ? Cl1 Co1 Cl2 103.48(6) . . ? C1 N1 C5 118.0(5) . . ? C1 N1 Co1 125.4(4) . . ? C5 N1 Co1 116.4(4) . . ? C7 N2 C8 110.6(4) . . ? C7 N2 C6 109.1(4) . . ? C8 N2 C6 111.1(4) . . ? C7 N2 Co1 118.9(3) . . ? C8 N2 Co1 103.7(3) . . ? C6 N2 Co1 103.1(3) . . ? C10 N3 C9 112.3(4) . . ? C10 N3 Co1 122.1(3) . . ? C9 N3 Co1 111.7(3) . . ? N1 C1 C2 123.3(6) . . ? C3 C2 C1 118.1(6) . . ? C4 C3 C2 119.8(6) . . ? C3 C4 C5 119.5(6) . . ? N1 C5 C4 121.3(5) . . ? N1 C5 C6 115.0(5) . . ? C4 C5 C6 123.6(5) . . ? C5 C6 N2 112.0(4) . . ? N2 C8 C9 109.9(4) . . ? N3 C9 C8 108.2(4) . . ? C15 C10 C11 121.5(5) . . ? C15 C10 N3 120.6(5) . . ? C11 C10 N3 117.9(5) . . ? C10 C11 C12 118.1(5) . . ? C10 C11 C16 122.4(5) . . ? C12 C11 C16 119.5(5) . . ? C13 C12 C11 121.2(6) . . ? C14 C13 C12 118.8(5) . . ? C14 C13 C17 120.2(6) . . ? C12 C13 C17 121.0(6) . . ? C13 C14 C15 121.9(5) . . ? C10 C15 C14 118.4(5) . . ? C10 C15 C18 123.4(5) . . ? C14 C15 C18 118.2(5) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.867 _refine_diff_density_min -0.746 _refine_diff_density_rms 0.120 data_04156 _database_code_depnum_ccdc_archive 'CCDC 270049' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H52 Cl4 Mn2 N8' _chemical_formula_weight 944.62 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.080(2) _cell_length_b 14.978(3) _cell_length_c 13.642(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.103(3) _cell_angle_gamma 90.00 _cell_volume 2216.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 934 _cell_measurement_theta_min 3.19 _cell_measurement_theta_max 27.53 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 0.852 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.815 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_process_details ; absorption correction based on 9169 reflections (SADABS); Rint 0.037 before correction and 0.024 after. ; _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15715 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3891 _reflns_number_gt 3301 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0379P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3891 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0693 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 Mn1 Mn 0.87190(3) -0.000178(18) 0.35539(2) 0.01707(10) Uani 1 1 d . . . Cl1 Cl 0.94117(5) -0.10955(3) 0.26312(4) 0.02228(13) Uani 1 1 d . . . Cl2 Cl 1.08212(4) 0.07509(3) 0.46436(4) 0.01940(13) Uani 1 1 d . . . N1 N 0.73728(14) 0.10546(10) 0.37910(12) 0.0180(4) Uani 1 1 d . . . N2 N 0.67692(15) -0.05784(10) 0.28794(13) 0.0209(4) Uani 1 1 d . . . N3 N 0.83231(15) 0.10574(10) 0.23028(13) 0.0203(4) Uani 1 1 d . . . N4 N 0.85602(15) 0.28169(11) 0.60202(13) 0.0231(4) Uani 1 1 d . . . H4 H 0.8993 0.2412 0.6455 0.028 Uiso 1 1 d R . . C1 C 0.63445(19) -0.12677(14) 0.21869(17) 0.0269(5) Uani 1 1 d . . . H1 H 0.6815 -0.1465 0.1825 0.032 Uiso 1 1 calc R . . C2 C 0.5263(2) -0.17022(15) 0.1976(2) 0.0388(6) Uani 1 1 d . . . H2 H 0.4980 -0.2180 0.1466 0.047 Uiso 1 1 calc R . . C3 C 0.4601(2) -0.14274(17) 0.2521(2) 0.0509(8) Uani 1 1 d . . . H3 H 0.3867 -0.1731 0.2417 0.061 Uiso 1 1 calc R . . C4 C 0.5009(2) -0.07082(16) 0.3219(2) 0.0402(6) Uani 1 1 d . . . H4A H 0.4549 -0.0501 0.3587 0.048 Uiso 1 1 calc R . . C5 C 0.60948(18) -0.02917(14) 0.33790(17) 0.0236(5) Uani 1 1 d . . . C6 C 0.65715(18) 0.05130(13) 0.41129(16) 0.0224(5) Uani 1 1 d . . . H6A H 0.5868 0.0880 0.4067 0.027 Uiso 1 1 calc R . . H6B H 0.7041 0.0314 0.4879 0.027 Uiso 1 1 calc R . . C7 C 0.89779(19) 0.11409(13) 0.17295(16) 0.0249(5) Uani 1 1 d . . . H7 H 0.9678 0.0769 0.1912 0.030 Uiso 1 1 calc R . . C8 C 0.8680(2) 0.17409(14) 0.08890(17) 0.0287(5) Uani 1 1 d . . . H8 H 0.9170 0.1789 0.0506 0.034 Uiso 1 1 calc R . . C9 C 0.7652(2) 0.22729(14) 0.06134(17) 0.0289(5) Uani 1 1 d . . . H9 H 0.7414 0.2683 0.0024 0.035 Uiso 1 1 calc R . . C10 C 0.69768(19) 0.22024(13) 0.12014(16) 0.0246(5) Uani 1 1 d . . . H10 H 0.6269 0.2564 0.1025 0.030 Uiso 1 1 calc R . . C11 C 0.73446(18) 0.15951(13) 0.20549(15) 0.0202(4) Uani 1 1 d . . . C12 C 0.66453(18) 0.15027(13) 0.27306(15) 0.0210(5) Uani 1 1 d . . . H12A H 0.6400 0.2103 0.2867 0.025 Uiso 1 1 calc R . . H12B H 0.5883 0.1156 0.2313 0.025 Uiso 1 1 calc R . . C13 C 0.81759(18) 0.16738(13) 0.46493(15) 0.0205(4) Uani 1 1 d . . . H13A H 0.8689 0.1998 0.4366 0.025 Uiso 1 1 calc R . . H13B H 0.8742 0.1311 0.5277 0.025 Uiso 1 1 calc R . . C14 C 0.75697(18) 0.23660(13) 0.50793(16) 0.0245(5) Uani 1 1 d . . . H14A H 0.7106 0.2806 0.4502 0.029 Uiso 1 1 calc R . . H14B H 0.6988 0.2071 0.5309 0.029 Uiso 1 1 calc R . . C15 C 0.81201(18) 0.34584(13) 0.65401(16) 0.0216(5) Uani 1 1 d . . . C16 C 0.80607(18) 0.32659(14) 0.75175(17) 0.0248(5) Uani 1 1 d . . . C17 C 0.7552(2) 0.38966(15) 0.79488(19) 0.0318(5) Uani 1 1 d . . . H17 H 0.7515 0.3775 0.8617 0.038 Uiso 1 1 calc R . . C18 C 0.7099(2) 0.46966(15) 0.7420(2) 0.0353(6) Uani 1 1 d . . . H18 H 0.6706 0.5106 0.7697 0.042 Uiso 1 1 calc R . . C19 C 0.7221(2) 0.48962(14) 0.64895(19) 0.0347(6) Uani 1 1 d . . . H19 H 0.6929 0.5454 0.6139 0.042 Uiso 1 1 calc R . . C20 C 0.7764(2) 0.42995(14) 0.60480(17) 0.0291(5) Uani 1 1 d . . . C21 C 0.8538(2) 0.23965(15) 0.80968(19) 0.0362(6) Uani 1 1 d . . . H21A H 0.9436 0.2378 0.8378 0.054 Uiso 1 1 calc R . . H21B H 0.8171 0.1901 0.7586 0.054 Uiso 1 1 calc R . . H21C H 0.8317 0.2342 0.8705 0.054 Uiso 1 1 calc R . . C22 C 0.8011(2) 0.45625(15) 0.50983(18) 0.0423(6) Uani 1 1 d . . . H22A H 0.7297 0.4407 0.4414 0.063 Uiso 1 1 calc R . . H22B H 0.8740 0.4244 0.5143 0.063 Uiso 1 1 calc R . . H22C H 0.8156 0.5208 0.5119 0.063 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 Mn1 0.01757(18) 0.01473(17) 0.01663(17) 0.00081(12) 0.00543(13) 0.00177(12) Cl1 0.0256(3) 0.0182(3) 0.0215(3) -0.0004(2) 0.0089(2) 0.0039(2) Cl2 0.0191(3) 0.0187(3) 0.0187(2) 0.0015(2) 0.0068(2) -0.0021(2) N1 0.0184(9) 0.0157(9) 0.0177(9) 0.0010(7) 0.0059(7) 0.0006(7) N2 0.0203(9) 0.0181(9) 0.0208(9) 0.0011(7) 0.0058(8) 0.0011(7) N3 0.0226(9) 0.0174(9) 0.0193(9) 0.0022(7) 0.0077(8) 0.0025(7) N4 0.0245(10) 0.0202(9) 0.0193(9) -0.0023(7) 0.0047(8) 0.0036(8) C1 0.0250(12) 0.0237(12) 0.0247(12) 0.0002(9) 0.0042(10) 0.0042(10) C2 0.0243(13) 0.0301(13) 0.0455(15) -0.0129(11) 0.0001(11) -0.0022(10) C3 0.0205(13) 0.0410(16) 0.085(2) -0.0158(15) 0.0173(14) -0.0103(11) C4 0.0234(13) 0.0368(14) 0.0619(18) -0.0095(13) 0.0202(13) -0.0022(11) C5 0.0189(11) 0.0196(11) 0.0284(12) 0.0038(9) 0.0068(10) 0.0027(9) C6 0.0212(11) 0.0227(11) 0.0237(11) 0.0016(9) 0.0103(9) 0.0026(9) C7 0.0253(12) 0.0224(11) 0.0275(12) 0.0017(9) 0.0119(10) 0.0052(9) C8 0.0346(13) 0.0289(12) 0.0263(12) 0.0044(10) 0.0168(11) 0.0019(10) C9 0.0409(14) 0.0224(12) 0.0214(11) 0.0074(9) 0.0119(10) 0.0067(10) C10 0.0271(12) 0.0203(11) 0.0218(11) 0.0031(9) 0.0064(10) 0.0064(9) C11 0.0221(11) 0.0147(10) 0.0177(10) -0.0024(8) 0.0033(9) 0.0005(9) C12 0.0196(11) 0.0185(11) 0.0197(10) 0.0007(9) 0.0039(9) 0.0047(9) C13 0.0190(11) 0.0207(11) 0.0190(10) -0.0005(9) 0.0058(9) 0.0012(9) C14 0.0219(11) 0.0230(11) 0.0249(12) -0.0044(9) 0.0071(9) 0.0017(9) C15 0.0178(11) 0.0199(11) 0.0230(11) -0.0054(9) 0.0050(9) -0.0009(9) C16 0.0201(11) 0.0248(12) 0.0318(12) -0.0031(10) 0.0134(10) -0.0026(9) C17 0.0322(13) 0.0342(13) 0.0366(13) -0.0079(11) 0.0221(11) -0.0037(11) C18 0.0288(13) 0.0277(13) 0.0488(16) -0.0153(12) 0.0166(12) -0.0017(10) C19 0.0395(14) 0.0205(12) 0.0337(14) -0.0058(10) 0.0066(11) 0.0055(10) C20 0.0323(13) 0.0244(12) 0.0216(11) -0.0048(9) 0.0035(10) 0.0015(10) C21 0.0458(15) 0.0353(14) 0.0398(14) 0.0071(11) 0.0300(13) 0.0070(11) C22 0.0661(18) 0.0268(13) 0.0277(13) 0.0034(11) 0.0149(13) 0.0048(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 Mn1 N3 2.2226(16) . ? Mn1 N2 2.2876(17) . ? Mn1 N1 2.3907(16) . ? Mn1 Cl1 2.4279(6) . ? Mn1 Cl2 2.5321(7) 3_756 ? Mn1 Cl2 2.5706(7) . ? Cl2 Mn1 2.5321(7) 3_756 ? N1 C6 1.470(2) . ? N1 C13 1.474(2) . ? N1 C12 1.482(2) . ? N2 C1 1.340(2) . ? N2 C5 1.342(2) . ? N3 C7 1.341(2) . ? N3 C11 1.345(2) . ? N4 C15 1.428(2) . ? N4 C14 1.478(2) . ? C1 C2 1.372(3) . ? C2 C3 1.373(3) . ? C3 C4 1.378(3) . ? C4 C5 1.380(3) . ? C5 C6 1.510(3) . ? C7 C8 1.374(3) . ? C8 C9 1.381(3) . ? C9 C10 1.377(3) . ? C10 C11 1.387(3) . ? C11 C12 1.506(3) . ? C13 C14 1.527(3) . ? C15 C16 1.397(3) . ? C15 C20 1.403(3) . ? C16 C17 1.391(3) . ? C16 C21 1.500(3) . ? C17 C18 1.382(3) . ? C18 C19 1.373(3) . ? C19 C20 1.392(3) . ? C20 C22 1.504(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Mn1 N2 97.18(6) . . ? N3 Mn1 N1 72.67(6) . . ? N2 Mn1 N1 70.30(6) . . ? N3 Mn1 Cl1 95.18(5) . . ? N2 Mn1 Cl1 93.76(4) . . ? N1 Mn1 Cl1 157.94(4) . . ? N3 Mn1 Cl2 160.58(4) . 3_756 ? N2 Mn1 Cl2 88.31(4) . 3_756 ? N1 Mn1 Cl2 91.92(4) . 3_756 ? Cl1 Mn1 Cl2 103.06(2) . 3_756 ? N3 Mn1 Cl2 87.43(4) . . ? N2 Mn1 Cl2 168.11(4) . . ? N1 Mn1 Cl2 100.91(4) . . ? Cl1 Mn1 Cl2 96.75(2) . . ? Cl2 Mn1 Cl2 83.913(19) 3_756 . ? Mn1 Cl2 Mn1 96.087(19) 3_756 . ? C6 N1 C13 113.56(15) . . ? C6 N1 C12 110.84(15) . . ? C13 N1 C12 113.00(15) . . ? C6 N1 Mn1 104.58(11) . . ? C13 N1 Mn1 105.94(11) . . ? C12 N1 Mn1 108.31(11) . . ? C1 N2 C5 118.35(18) . . ? C1 N2 Mn1 125.57(14) . . ? C5 N2 Mn1 115.00(13) . . ? C7 N3 C11 118.45(17) . . ? C7 N3 Mn1 122.12(13) . . ? C11 N3 Mn1 119.27(13) . . ? C15 N4 C14 113.74(15) . . ? N2 C1 C2 123.2(2) . . ? C1 C2 C3 118.1(2) . . ? C2 C3 C4 119.5(2) . . ? C3 C4 C5 119.3(2) . . ? N2 C5 C4 121.5(2) . . ? N2 C5 C6 116.91(17) . . ? C4 C5 C6 121.61(19) . . ? N1 C6 C5 110.58(16) . . ? N3 C7 C8 122.86(19) . . ? C7 C8 C9 118.6(2) . . ? C10 C9 C8 119.30(19) . . ? C9 C10 C11 119.08(19) . . ? N3 C11 C10 121.68(19) . . ? N3 C11 C12 117.31(17) . . ? C10 C11 C12 121.00(18) . . ? N1 C12 C11 112.81(16) . . ? N1 C13 C14 118.22(16) . . ? N4 C14 C13 107.57(16) . . ? C16 C15 C20 120.55(19) . . ? C16 C15 N4 121.46(18) . . ? C20 C15 N4 117.99(18) . . ? C17 C16 C15 118.79(19) . . ? C17 C16 C21 120.35(19) . . ? C15 C16 C21 120.86(18) . . ? C18 C17 C16 121.0(2) . . ? C19 C18 C17 119.5(2) . . ? C18 C19 C20 121.5(2) . . ? C19 C20 C15 118.2(2) . . ? C19 C20 C22 120.9(2) . . ? C15 C20 C22 120.8(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.340 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.054 data_2114 _database_code_depnum_ccdc_archive 'CCDC 270050' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C22 H26 Cl2 N4 Fe) (C2 H3 N)' _chemical_formula_sum 'C24 H29 Cl2 N5 Fe)' _chemical_formula_weight 514.27 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' Fe Fe 0.3463 0.8444 '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 19.206(4) _cell_length_b 14.800(3) _cell_length_c 17.270(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.752(4) _cell_angle_gamma 90.00 _cell_volume 4838.1(18) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1464 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 26.82 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 0.866 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.59 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_process_details ; absorption correction based on 1337 reflections (SADABS); Rint 0.054 before correction and 0.036 after. ; _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26576 _diffrn_reflns_av_R_equivalents 0.1551 _diffrn_reflns_av_sigmaI/netI 0.2103 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8503 _reflns_number_gt 3963 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0734P)^2^+0.0000P] 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 0.0042(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8503 _refine_ls_number_parameters 584 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1670 _refine_ls_R_factor_gt 0.0787 _refine_ls_wR_factor_ref 0.1970 _refine_ls_wR_factor_gt 0.1608 _refine_ls_goodness_of_fit_ref 0.882 _refine_ls_restrained_S_all 0.882 _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 Fe1 Fe 0.47304(6) 0.22325(8) 0.05918(6) 0.0286(3) Uani 1 1 d . . . Cl1 Cl 0.52886(11) 0.25517(16) 0.18727(12) 0.0412(6) Uani 1 1 d . . . Cl2 Cl 0.55790(11) 0.11238(14) 0.02271(11) 0.0348(5) Uani 1 1 d . . . N1 N 0.5185(3) 0.3293(5) -0.0054(4) 0.0328(17) Uani 1 1 d . . . N2 N 0.4094(3) 0.2223(4) -0.0628(4) 0.0321(17) Uani 1 1 d . . . N3 N 0.3794(3) 0.2998(4) 0.0721(4) 0.0326(17) Uani 1 1 d . . . N4 N 0.3997(3) 0.1006(4) 0.0621(3) 0.0289(16) Uani 1 1 d . . . H4' H 0.4287 0.0512 0.0573 0.035 Uiso 1 1 calc R . . C1 C 0.5617(4) 0.3956(6) 0.0264(5) 0.040(2) Uani 1 1 d . . . H1 H 0.5736 0.3984 0.0820 0.048 Uiso 1 1 calc R . . C2 C 0.5895(5) 0.4593(6) -0.0168(5) 0.044(2) Uani 1 1 d . . . H2 H 0.6194 0.5056 0.0082 0.053 Uiso 1 1 calc R . . C3 C 0.5726(5) 0.4546(6) -0.0989(6) 0.051(3) Uani 1 1 d . . . H3 H 0.5912 0.4976 -0.1308 0.062 Uiso 1 1 calc R . . C4 C 0.5287(4) 0.3863(5) -0.1325(5) 0.035(2) Uani 1 1 d . . . H4 H 0.5165 0.3818 -0.1881 0.042 Uiso 1 1 calc R . . C5 C 0.5026(4) 0.3245(5) -0.0845(5) 0.031(2) Uani 1 1 d . . . C6 C 0.4574(4) 0.2480(6) -0.1172(5) 0.035(2) Uani 1 1 d . . . H6A H 0.4294 0.2654 -0.1686 0.041 Uiso 1 1 calc R . . H6B H 0.4873 0.1957 -0.1258 0.041 Uiso 1 1 calc R . . C7 C 0.3511(4) 0.2884(5) -0.0686(5) 0.035(2) Uani 1 1 d . . . H7A H 0.3095 0.2637 -0.1039 0.042 Uiso 1 1 calc R . . H7B H 0.3655 0.3444 -0.0930 0.042 Uiso 1 1 calc R . . C8 C 0.3298(4) 0.3121(5) 0.0092(5) 0.032(2) Uani 1 1 d . . . C9 C 0.2646(4) 0.3492(6) 0.0103(6) 0.045(2) Uani 1 1 d . . . H9 H 0.2316 0.3562 -0.0368 0.054 Uiso 1 1 calc R . . C10 C 0.2477(5) 0.3769(6) 0.0835(6) 0.053(3) Uani 1 1 d . . . H10 H 0.2034 0.4034 0.0871 0.063 Uiso 1 1 calc R . . C11 C 0.2980(5) 0.3637(6) 0.1486(6) 0.045(2) Uani 1 1 d . . . H11 H 0.2888 0.3816 0.1987 0.054 Uiso 1 1 calc R . . C12 C 0.3612(4) 0.3252(6) 0.1423(5) 0.037(2) Uani 1 1 d . . . H12 H 0.3944 0.3154 0.1890 0.044 Uiso 1 1 calc R . . C13 C 0.3812(4) 0.1301(6) -0.0776(5) 0.036(2) Uani 1 1 d . . . H13A H 0.4201 0.0885 -0.0841 0.043 Uiso 1 1 calc R . . H13B H 0.3464 0.1295 -0.1269 0.043 Uiso 1 1 calc R . . C14 C 0.3463(4) 0.0978(5) -0.0108(4) 0.031(2) Uani 1 1 d . . . H14A H 0.3058 0.1372 -0.0053 0.037 Uiso 1 1 calc R . . H14B H 0.3287 0.0353 -0.0210 0.037 Uiso 1 1 calc R . . C15 C 0.3687(4) 0.0798(5) 0.1318(4) 0.0270(19) Uani 1 1 d . . . C16 C 0.4073(4) 0.0243(6) 0.1902(5) 0.033(2) Uani 1 1 d . . . C17 C 0.3745(4) 0.0009(6) 0.2539(5) 0.039(2) Uani 1 1 d . . . H17 H 0.3989 -0.0377 0.2934 0.047 Uiso 1 1 calc R . . C18 C 0.3067(4) 0.0325(6) 0.2617(5) 0.034(2) Uani 1 1 d . . . C19 C 0.2728(4) 0.0907(6) 0.2064(5) 0.040(2) Uani 1 1 d . . . H19 H 0.2281 0.1150 0.2119 0.048 Uiso 1 1 calc R . . C20 C 0.3041(4) 0.1146(6) 0.1414(5) 0.038(2) Uani 1 1 d . . . H20 H 0.2803 0.1554 0.1034 0.045 Uiso 1 1 calc R . . C21 C 0.4776(4) -0.0115(6) 0.1835(5) 0.038(2) Uani 1 1 d . . . H21A H 0.4943 -0.0510 0.2284 0.058 Uiso 1 1 calc R . . H21B H 0.5108 0.0387 0.1830 0.058 Uiso 1 1 calc R . . H21C H 0.4745 -0.0461 0.1346 0.058 Uiso 1 1 calc R . . C22 C 0.2707(5) -0.0028(7) 0.3274(5) 0.057(3) Uani 1 1 d . . . H22A H 0.2556 0.0482 0.3567 0.086 Uiso 1 1 calc R . . H22B H 0.3039 -0.0405 0.3629 0.086 Uiso 1 1 calc R . . H22C H 0.2294 -0.0390 0.3050 0.086 Uiso 1 1 calc R . . Fe1A Fe 0.14425(6) 0.68275(8) 0.23832(7) 0.0308(3) Uani 1 1 d . . . Cl1A Cl 0.03644(11) 0.74633(15) 0.18991(13) 0.0410(6) Uani 1 1 d . . . Cl2A Cl 0.13684(11) 0.54568(15) 0.14918(12) 0.0394(6) Uani 1 1 d . . . N1A N 0.2101(3) 0.7608(5) 0.1721(4) 0.0316(17) Uani 1 1 d . . . N2A N 0.2559(3) 0.6482(4) 0.2885(4) 0.0305(16) Uani 1 1 d . . . N3A N 0.1680(3) 0.7743(4) 0.3392(4) 0.0309(16) Uani 1 1 d . . . N4A N 0.1285(3) 0.5731(4) 0.3297(4) 0.0312(17) Uani 1 1 d . . . H4A' H 0.1172 0.5209 0.3002 0.037 Uiso 1 1 calc R . . C1A C 0.1897(4) 0.8374(6) 0.1318(4) 0.036(2) Uani 1 1 d . . . H1A H 0.1424 0.8576 0.1286 0.043 Uiso 1 1 calc R . . C2A C 0.2355(4) 0.8870(6) 0.0953(5) 0.037(2) Uani 1 1 d . . . H2A H 0.2198 0.9407 0.0676 0.044 Uiso 1 1 calc R . . C3A C 0.3041(5) 0.8582(6) 0.0991(5) 0.040(2) Uani 1 1 d . . . H3A H 0.3359 0.8914 0.0735 0.048 Uiso 1 1 calc R . . C4A C 0.3260(4) 0.7819(6) 0.1398(4) 0.032(2) Uani 1 1 d . . . H4A H 0.3734 0.7613 0.1437 0.039 Uiso 1 1 calc R . . C5A C 0.2776(4) 0.7348(5) 0.1755(4) 0.031(2) Uani 1 1 d . . . C6A C 0.2963(4) 0.6483(5) 0.2226(4) 0.032(2) Uani 1 1 d . . . H6A1 H 0.2837 0.5947 0.1888 0.039 Uiso 1 1 calc R . . H6A2 H 0.3476 0.6463 0.2431 0.039 Uiso 1 1 calc R . . C7A C 0.2879(4) 0.7166(6) 0.3480(4) 0.035(2) Uani 1 1 d . . . H7A1 H 0.3160 0.7602 0.3226 0.042 Uiso 1 1 calc R . . H7A2 H 0.3203 0.6857 0.3905 0.042 Uiso 1 1 calc R . . C8A C 0.2320(4) 0.7677(5) 0.3834(5) 0.031(2) Uani 1 1 d . . . C9A C 0.2499(5) 0.8104(6) 0.4548(5) 0.038(2) Uani 1 1 d . . . H9A H 0.2959 0.8041 0.4847 0.045 Uiso 1 1 calc R . . C10A C 0.1993(5) 0.8630(6) 0.4824(5) 0.046(2) Uani 1 1 d . . . H10A H 0.2101 0.8936 0.5313 0.055 Uiso 1 1 calc R . . C11A C 0.1340(5) 0.8696(6) 0.4378(5) 0.049(3) Uani 1 1 d . . . H11A H 0.0986 0.9050 0.4555 0.059 Uiso 1 1 calc R . . C12A C 0.1194(5) 0.8251(6) 0.3673(5) 0.041(2) Uani 1 1 d . . . H12A H 0.0735 0.8302 0.3370 0.049 Uiso 1 1 calc R . . C13A C 0.2552(4) 0.5576(5) 0.3247(5) 0.036(2) Uani 1 1 d . . . H13C H 0.3020 0.5447 0.3566 0.043 Uiso 1 1 calc R . . H13D H 0.2453 0.5111 0.2832 0.043 Uiso 1 1 calc R . . C14A C 0.1984(4) 0.5548(6) 0.3768(4) 0.030(2) Uani 1 1 d . . . H14C H 0.1982 0.4945 0.4017 0.036 Uiso 1 1 calc R . . H14D H 0.2091 0.6005 0.4190 0.036 Uiso 1 1 calc R . . C15A C 0.0712(4) 0.5848(6) 0.3721(4) 0.031(2) Uani 1 1 d . . . C16A C 0.0059(4) 0.5492(6) 0.3435(5) 0.033(2) Uani 1 1 d . . . C17A C -0.0492(5) 0.5639(6) 0.3852(5) 0.040(2) Uani 1 1 d . . . H17A H -0.0942 0.5386 0.3655 0.048 Uiso 1 1 calc R . . C18A C -0.0416(4) 0.6135(6) 0.4538(5) 0.039(2) Uani 1 1 d . . . C19A C 0.0250(4) 0.6474(6) 0.4833(4) 0.034(2) Uani 1 1 d . . . H19A H 0.0322 0.6795 0.5316 0.041 Uiso 1 1 calc R . . C20A C 0.0812(4) 0.6351(5) 0.4432(4) 0.032(2) Uani 1 1 d . . . H20A H 0.1261 0.6602 0.4633 0.039 Uiso 1 1 calc R . . C21A C -0.0069(5) 0.4934(6) 0.2683(5) 0.052(3) Uani 1 1 d . . . H21D H 0.0222 0.4387 0.2755 0.078 Uiso 1 1 calc R . . H21E H 0.0057 0.5291 0.2250 0.078 Uiso 1 1 calc R . . H21F H -0.0569 0.4764 0.2561 0.078 Uiso 1 1 calc R . . C22A C -0.1035(4) 0.6263(6) 0.4988(5) 0.053(3) Uani 1 1 d . . . H22D H -0.1355 0.6728 0.4728 0.079 Uiso 1 1 calc R . . H22E H -0.0852 0.6450 0.5529 0.079 Uiso 1 1 calc R . . H22F H -0.1292 0.5692 0.4994 0.079 Uiso 1 1 calc R . . N5 N 0.7947(5) 0.8353(6) 0.1764(6) 0.069(3) Uani 1 1 d . . . C23 C 0.8373(5) 0.8105(7) 0.2254(7) 0.048(3) Uani 1 1 d . . . C24 C 0.8904(5) 0.7797(7) 0.2900(6) 0.064(3) Uani 1 1 d . . . H24A H 0.8674 0.7599 0.3336 0.095 Uiso 1 1 calc R . . H24B H 0.9230 0.8294 0.3077 0.095 Uiso 1 1 calc R . . H24C H 0.9168 0.7292 0.2724 0.095 Uiso 1 1 calc R . . N6 N 0.8747(5) 0.6189(8) 0.1311(7) 0.091(4) Uani 1 1 d . . . C25 C 0.9127(6) 0.6147(8) 0.0864(8) 0.064(3) Uani 1 1 d . . . C26 C 0.9632(5) 0.6125(7) 0.0331(6) 0.074(3) Uani 1 1 d . . . H26A H 0.9693 0.6736 0.0133 0.111 Uiso 1 1 calc R . . H26B H 0.9459 0.5723 -0.0111 0.111 Uiso 1 1 calc R . . H26C H 1.0087 0.5902 0.0610 0.111 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 Fe1 0.0369(7) 0.0224(7) 0.0267(6) -0.0018(5) 0.0057(5) -0.0012(6) Cl1 0.0481(13) 0.0434(15) 0.0307(11) -0.0053(10) 0.0028(10) 0.0009(11) Cl2 0.0406(13) 0.0292(13) 0.0355(12) -0.0014(10) 0.0095(10) 0.0002(10) N1 0.038(4) 0.031(5) 0.029(4) 0.000(3) 0.002(3) -0.001(3) N2 0.039(4) 0.024(4) 0.034(4) 0.002(3) 0.009(3) 0.000(3) N3 0.043(4) 0.024(4) 0.033(4) -0.007(3) 0.013(3) -0.009(3) N4 0.035(4) 0.025(4) 0.027(4) 0.000(3) 0.006(3) 0.005(3) C1 0.052(6) 0.017(5) 0.050(6) -0.005(4) 0.004(5) 0.001(4) C2 0.059(6) 0.020(5) 0.055(6) -0.003(5) 0.016(5) -0.012(5) C3 0.061(7) 0.029(6) 0.066(7) 0.012(5) 0.015(5) -0.002(5) C4 0.050(6) 0.020(5) 0.034(5) 0.003(4) 0.008(4) -0.004(4) C5 0.044(5) 0.015(5) 0.036(5) 0.005(4) 0.010(4) -0.001(4) C6 0.034(5) 0.039(6) 0.035(5) -0.002(4) 0.019(4) -0.002(4) C7 0.046(5) 0.016(5) 0.040(5) 0.004(4) 0.001(4) 0.007(4) C8 0.037(5) 0.019(5) 0.041(5) 0.003(4) 0.010(4) -0.001(4) C9 0.038(5) 0.037(6) 0.060(6) 0.008(5) 0.005(5) 0.008(5) C10 0.061(7) 0.021(6) 0.085(8) 0.005(5) 0.034(6) 0.013(5) C11 0.055(6) 0.026(6) 0.061(7) -0.006(5) 0.031(5) -0.004(5) C12 0.044(5) 0.028(5) 0.043(5) -0.005(4) 0.022(4) -0.009(4) C13 0.044(5) 0.029(6) 0.033(5) 0.004(4) 0.003(4) -0.003(4) C14 0.028(5) 0.023(5) 0.042(5) 0.000(4) 0.008(4) -0.007(4) C15 0.030(5) 0.022(5) 0.033(5) -0.002(4) 0.017(4) -0.001(4) C16 0.039(5) 0.027(5) 0.031(5) -0.009(4) 0.005(4) 0.007(4) C17 0.051(6) 0.039(6) 0.030(5) 0.001(4) 0.012(4) -0.007(5) C18 0.041(5) 0.032(6) 0.033(5) -0.005(4) 0.020(4) -0.008(4) C19 0.042(5) 0.034(6) 0.047(6) -0.001(5) 0.017(5) 0.006(4) C20 0.050(6) 0.029(6) 0.034(5) 0.001(4) 0.007(4) -0.004(5) C21 0.039(5) 0.046(6) 0.031(5) -0.008(4) 0.009(4) 0.008(5) C22 0.065(7) 0.065(8) 0.046(6) 0.003(5) 0.020(5) -0.007(6) Fe1A 0.0358(7) 0.0270(8) 0.0289(7) 0.0013(6) 0.0036(5) 0.0013(6) Cl1A 0.0406(13) 0.0372(14) 0.0436(13) -0.0001(10) 0.0022(10) 0.0060(11) Cl2A 0.0535(14) 0.0327(14) 0.0332(12) -0.0028(10) 0.0109(10) 0.0025(11) N1A 0.035(4) 0.030(5) 0.025(4) -0.007(3) -0.009(3) 0.000(3) N2A 0.045(4) 0.022(4) 0.027(4) 0.001(3) 0.013(3) -0.001(3) N3A 0.037(4) 0.021(4) 0.036(4) -0.001(3) 0.011(3) 0.000(3) N4A 0.037(4) 0.024(4) 0.034(4) -0.002(3) 0.008(3) 0.006(3) C1A 0.041(5) 0.038(6) 0.027(5) -0.006(4) 0.005(4) -0.003(5) C2A 0.043(5) 0.026(5) 0.041(5) 0.003(4) 0.006(4) 0.000(4) C3A 0.059(6) 0.031(6) 0.033(5) -0.001(4) 0.014(5) -0.006(5) C4A 0.030(5) 0.037(6) 0.033(5) -0.006(4) 0.012(4) -0.005(4) C5A 0.043(5) 0.020(5) 0.027(4) -0.004(4) -0.002(4) 0.003(4) C6A 0.035(5) 0.025(5) 0.038(5) 0.000(4) 0.008(4) 0.001(4) C7A 0.039(5) 0.034(6) 0.032(5) 0.005(4) 0.004(4) -0.004(4) C8A 0.037(5) 0.024(5) 0.031(5) 0.008(4) 0.006(4) -0.001(4) C9A 0.049(6) 0.036(6) 0.027(5) -0.001(4) 0.007(4) -0.010(5) C10A 0.076(7) 0.025(6) 0.040(5) -0.012(4) 0.020(5) -0.004(5) C11A 0.064(7) 0.044(7) 0.046(6) -0.014(5) 0.025(5) -0.005(5) C12A 0.061(6) 0.019(5) 0.046(6) 0.010(4) 0.017(5) 0.006(5) C13A 0.041(5) 0.024(5) 0.042(5) 0.007(4) 0.006(4) 0.008(4) C14A 0.031(5) 0.026(5) 0.035(5) 0.001(4) 0.014(4) 0.004(4) C15A 0.029(5) 0.037(6) 0.027(4) 0.005(4) 0.008(4) -0.001(4) C16A 0.032(5) 0.026(5) 0.041(5) -0.004(4) 0.008(4) 0.006(4) C17A 0.047(6) 0.020(5) 0.051(6) 0.006(4) 0.002(5) -0.007(4) C18A 0.044(6) 0.040(6) 0.034(5) 0.007(4) 0.010(4) -0.003(5) C19A 0.043(5) 0.035(6) 0.026(5) 0.000(4) 0.013(4) 0.007(4) C20A 0.032(5) 0.031(5) 0.035(5) -0.005(4) 0.008(4) -0.002(4) C21A 0.068(7) 0.041(7) 0.046(6) -0.010(5) 0.005(5) -0.014(5) C22A 0.051(6) 0.050(7) 0.062(7) -0.010(5) 0.021(5) -0.004(5) N5 0.061(6) 0.057(7) 0.086(7) -0.001(5) 0.004(5) 0.008(5) C23 0.041(6) 0.035(6) 0.073(8) -0.002(6) 0.021(5) -0.004(5) C24 0.060(7) 0.075(9) 0.058(7) 0.013(6) 0.018(6) 0.000(6) N6 0.069(8) 0.090(9) 0.108(10) 0.000(7) -0.003(6) -0.008(7) C25 0.054(8) 0.044(7) 0.084(10) -0.007(7) -0.021(6) 0.006(6) C26 0.077(8) 0.050(8) 0.089(9) -0.017(7) -0.004(7) 0.013(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 Fe1 N3 2.169(7) . ? Fe1 N1 2.191(7) . ? Fe1 N2 2.249(6) . ? Fe1 N4 2.303(6) . ? Fe1 Cl1 2.337(2) . ? Fe1 Cl2 2.468(2) . ? N1 C1 1.341(10) . ? N1 C5 1.351(9) . ? N2 C6 1.474(9) . ? N2 C13 1.475(10) . ? N2 C7 1.477(9) . ? N3 C8 1.330(9) . ? N3 C12 1.370(9) . ? N4 C15 1.464(9) . ? N4 C14 1.484(9) . ? C1 C2 1.365(11) . ? C2 C3 1.402(11) . ? C3 C4 1.380(11) . ? C4 C5 1.384(10) . ? C5 C6 1.481(10) . ? C7 C8 1.512(10) . ? C8 C9 1.369(10) . ? C9 C10 1.418(12) . ? C10 C11 1.366(12) . ? C11 C12 1.363(11) . ? C13 C14 1.506(10) . ? C15 C20 1.379(10) . ? C15 C16 1.410(10) . ? C16 C17 1.400(10) . ? C16 C21 1.474(10) . ? C17 C18 1.412(11) . ? C18 C19 1.367(11) . ? C18 C22 1.518(10) . ? C19 C20 1.405(11) . ? Fe1A N1A 2.175(7) . ? Fe1A N3A 2.192(7) . ? Fe1A N2A 2.231(7) . ? Fe1A Cl1A 2.299(2) . ? Fe1A N4A 2.319(6) . ? Fe1A Cl2A 2.536(2) . ? N1A C5A 1.345(9) . ? N1A C1A 1.352(10) . ? N2A C13A 1.480(9) . ? N2A C6A 1.483(9) . ? N2A C7A 1.498(9) . ? N3A C8A 1.337(9) . ? N3A C12A 1.350(10) . ? N4A C15A 1.431(9) . ? N4A C14A 1.474(9) . ? C1A C2A 1.378(10) . ? C2A C3A 1.374(10) . ? C3A C4A 1.359(11) . ? C4A C5A 1.387(10) . ? C5A C6A 1.527(10) . ? C7A C8A 1.523(10) . ? C8A C9A 1.377(10) . ? C9A C10A 1.390(11) . ? C10A C11A 1.359(12) . ? C11A C12A 1.372(11) . ? C13A C14A 1.528(9) . ? C15A C16A 1.373(10) . ? C15A C20A 1.420(10) . ? C16A C17A 1.395(11) . ? C16A C21A 1.523(11) . ? C17A C18A 1.379(11) . ? C18A C19A 1.387(11) . ? C18A C22A 1.539(10) . ? C19A C20A 1.389(10) . ? N5 C23 1.133(11) . ? C23 C24 1.453(13) . ? N6 C25 1.151(14) . ? C25 C26 1.446(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Fe1 N1 95.0(2) . . ? N3 Fe1 N2 76.7(2) . . ? N1 Fe1 N2 74.2(2) . . ? N3 Fe1 N4 83.6(2) . . ? N1 Fe1 N4 150.9(2) . . ? N2 Fe1 N4 77.2(2) . . ? N3 Fe1 Cl1 93.02(18) . . ? N1 Fe1 Cl1 100.28(18) . . ? N2 Fe1 Cl1 167.69(19) . . ? N4 Fe1 Cl1 108.82(16) . . ? N3 Fe1 Cl2 165.55(18) . . ? N1 Fe1 Cl2 90.55(18) . . ? N2 Fe1 Cl2 91.99(17) . . ? N4 Fe1 Cl2 85.08(16) . . ? Cl1 Fe1 Cl2 99.15(8) . . ? C1 N1 C5 118.1(7) . . ? C1 N1 Fe1 126.0(6) . . ? C5 N1 Fe1 115.9(5) . . ? C6 N2 C13 112.2(6) . . ? C6 N2 C7 109.5(6) . . ? C13 N2 C7 110.5(6) . . ? C6 N2 Fe1 107.3(5) . . ? C13 N2 Fe1 107.1(5) . . ? C7 N2 Fe1 110.2(5) . . ? C8 N3 C12 115.5(7) . . ? C8 N3 Fe1 118.7(5) . . ? C12 N3 Fe1 125.0(6) . . ? C15 N4 C14 111.9(6) . . ? C15 N4 Fe1 121.3(5) . . ? C14 N4 Fe1 109.9(4) . . ? N1 C1 C2 123.6(9) . . ? C1 C2 C3 118.3(9) . . ? C4 C3 C2 118.8(8) . . ? C3 C4 C5 119.3(8) . . ? N1 C5 C4 122.0(8) . . ? N1 C5 C6 116.3(7) . . ? C4 C5 C6 121.7(7) . . ? N2 C6 C5 110.1(6) . . ? N2 C7 C8 114.1(6) . . ? N3 C8 C9 125.0(8) . . ? N3 C8 C7 115.4(7) . . ? C9 C8 C7 119.4(8) . . ? C8 C9 C10 118.4(9) . . ? C11 C10 C9 117.1(9) . . ? C12 C11 C10 120.6(9) . . ? C11 C12 N3 123.3(8) . . ? N2 C13 C14 111.0(7) . . ? N4 C14 C13 107.9(6) . . ? C20 C15 C16 120.4(7) . . ? C20 C15 N4 121.4(7) . . ? C16 C15 N4 118.2(7) . . ? C17 C16 C15 117.0(7) . . ? C17 C16 C21 120.8(8) . . ? C15 C16 C21 122.1(7) . . ? C16 C17 C18 122.5(8) . . ? C19 C18 C17 118.7(7) . . ? C19 C18 C22 121.1(8) . . ? C17 C18 C22 120.1(8) . . ? C18 C19 C20 119.9(8) . . ? C15 C20 C19 121.2(8) . . ? N1A Fe1A N3A 91.6(2) . . ? N1A Fe1A N2A 73.8(2) . . ? N3A Fe1A N2A 77.1(2) . . ? N1A Fe1A Cl1A 99.17(19) . . ? N3A Fe1A Cl1A 95.13(19) . . ? N2A Fe1A Cl1A 169.09(18) . . ? N1A Fe1A N4A 152.2(2) . . ? N3A Fe1A N4A 85.7(2) . . ? N2A Fe1A N4A 78.6(2) . . ? Cl1A Fe1A N4A 108.68(17) . . ? N1A Fe1A Cl2A 94.81(18) . . ? N3A Fe1A Cl2A 163.57(19) . . ? N2A Fe1A Cl2A 90.23(17) . . ? Cl1A Fe1A Cl2A 98.75(8) . . ? N4A Fe1A Cl2A 81.55(17) . . ? C5A N1A C1A 117.0(7) . . ? C5A N1A Fe1A 117.9(5) . . ? C1A N1A Fe1A 125.0(6) . . ? C13A N2A C6A 111.6(6) . . ? C13A N2A C7A 110.8(6) . . ? C6A N2A C7A 108.5(6) . . ? C13A N2A Fe1A 107.2(5) . . ? C6A N2A Fe1A 107.1(5) . . ? C7A N2A Fe1A 111.6(5) . . ? C8A N3A C12A 117.4(7) . . ? C8A N3A Fe1A 117.2(5) . . ? C12A N3A Fe1A 124.5(6) . . ? C15A N4A C14A 116.5(6) . . ? C15A N4A Fe1A 117.7(5) . . ? C14A N4A Fe1A 107.0(4) . . ? N1A C1A C2A 122.1(8) . . ? C3A C2A C1A 119.5(8) . . ? C4A C3A C2A 119.6(8) . . ? C3A C4A C5A 118.3(8) . . ? N1A C5A C4A 123.4(8) . . ? N1A C5A C6A 113.6(7) . . ? C4A C5A C6A 122.9(8) . . ? N2A C6A C5A 107.7(6) . . ? N2A C7A C8A 112.0(6) . . ? N3A C8A C9A 123.0(8) . . ? N3A C8A C7A 116.7(7) . . ? C9A C8A C7A 120.1(7) . . ? C8A C9A C10A 118.8(8) . . ? C11A C10A C9A 118.5(8) . . ? C10A C11A C12A 119.9(9) . . ? N3A C12A C11A 122.5(9) . . ? N2A C13A C14A 109.4(6) . . ? N4A C14A C13A 110.2(6) . . ? C16A C15A C20A 119.6(7) . . ? C16A C15A N4A 120.2(7) . . ? C20A C15A N4A 120.2(7) . . ? C15A C16A C17A 118.7(8) . . ? C15A C16A C21A 121.4(7) . . ? C17A C16A C21A 119.8(8) . . ? C18A C17A C16A 123.1(8) . . ? C17A C18A C19A 117.7(8) . . ? C17A C18A C22A 121.3(8) . . ? C19A C18A C22A 120.9(8) . . ? C18A C19A C20A 121.0(8) . . ? C19A C20A C15A 119.8(7) . . ? N5 C23 C24 178.1(12) . . ? N6 C25 C26 176.8(13) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.995 _refine_diff_density_min -0.857 _refine_diff_density_rms 0.112 data_03118 _database_code_depnum_ccdc_archive 'CCDC 270051' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C22 H26 Cl2 Fe N4)(C2 H3 N)' _chemical_formula_sum 'C24 H29 Cl2 Fe N5' _chemical_formula_weight 514.27 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' Fe Fe 0.3463 0.8444 '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 7.5084(13) _cell_length_b 12.873(2) _cell_length_c 12.978(2) _cell_angle_alpha 82.257(3) _cell_angle_beta 86.705(3) _cell_angle_gamma 83.201(3) _cell_volume 1233.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4612 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 28.20 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.850 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.710 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details ; absorption correction based on 6134 reflections (SADABS); Rint 0.33 before correction and 0.022 after. ; _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9702 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _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 1.58 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4770 _reflns_number_gt 4114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0480P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4770 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0883 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 Fe1 Fe 0.24973(3) 0.27029(2) 0.31671(2) 0.02340(10) Uani 1 1 d . . . Cl1 Cl 0.48456(7) 0.22047(4) 0.42805(4) 0.03945(15) Uani 1 1 d . . . Cl2 Cl 0.34196(7) 0.44296(4) 0.24211(4) 0.03154(14) Uani 1 1 d . . . N1 N 0.0391(2) 0.34090(12) 0.41556(12) 0.0243(4) Uani 1 1 d . . . N2 N 0.0019(2) 0.29688(12) 0.22099(12) 0.0227(4) Uani 1 1 d . . . N3 N 0.1435(2) 0.11757(12) 0.34938(12) 0.0244(4) Uani 1 1 d . . . N4 N 0.3604(2) 0.23625(13) 0.13284(13) 0.0261(4) Uani 1 1 d . . . H4A H 0.3796 0.3066 0.1356 0.039 Uiso 1 1 d R . . C1 C 0.0446(3) 0.34096(15) 0.51858(16) 0.0278(4) Uani 1 1 d . . . H1 H 0.1446 0.3061 0.5525 0.033 Uiso 1 1 calc R . . C2 C -0.0913(3) 0.39028(16) 0.57625(17) 0.0334(5) Uani 1 1 d . . . H2 H -0.0830 0.3889 0.6477 0.040 Uiso 1 1 calc R . . C3 C -0.2391(3) 0.44153(17) 0.52641(18) 0.0353(5) Uani 1 1 d . . . H3 H -0.3314 0.4769 0.5635 0.042 Uiso 1 1 calc R . . C4 C -0.2497(3) 0.44021(16) 0.42119(17) 0.0313(5) Uani 1 1 d . . . H4 H -0.3512 0.4720 0.3866 0.038 Uiso 1 1 calc R . . C5 C -0.1069(3) 0.39072(15) 0.36773(15) 0.0249(4) Uani 1 1 d . . . C6 C -0.1023(3) 0.39325(15) 0.25193(15) 0.0275(4) Uani 1 1 d . . . H6A H -0.2238 0.3984 0.2286 0.033 Uiso 1 1 calc R . . H6B H -0.0481 0.4548 0.2191 0.033 Uiso 1 1 calc R . . C7 C -0.1054(3) 0.20626(15) 0.24733(16) 0.0276(4) Uani 1 1 d . . . H7A H -0.1535 0.1908 0.1840 0.033 Uiso 1 1 calc R . . H7B H -0.2062 0.2267 0.2933 0.033 Uiso 1 1 calc R . . C8 C -0.0023(3) 0.10742(15) 0.29874(15) 0.0254(4) Uani 1 1 d . . . C9 C -0.0648(3) 0.01121(17) 0.29801(18) 0.0390(5) Uani 1 1 d . . . H9 H -0.1644 0.0061 0.2604 0.047 Uiso 1 1 calc R . . C10 C 0.0215(3) -0.07721(18) 0.3534(2) 0.0471(6) Uani 1 1 d . . . H10 H -0.0171 -0.1431 0.3524 0.057 Uiso 1 1 calc R . . C11 C 0.1662(3) -0.06653(17) 0.41047(18) 0.0387(5) Uani 1 1 d . . . H11 H 0.2233 -0.1243 0.4514 0.046 Uiso 1 1 calc R . . C12 C 0.2235(3) 0.03102(16) 0.40541(16) 0.0302(5) Uani 1 1 d . . . H12 H 0.3228 0.0378 0.4426 0.036 Uiso 1 1 calc R . . C13 C 0.0506(3) 0.31287(16) 0.10820(15) 0.0283(5) Uani 1 1 d . . . H13A H 0.0926 0.3817 0.0901 0.034 Uiso 1 1 calc R . . H13B H -0.0551 0.3114 0.0690 0.034 Uiso 1 1 calc R . . C14 C 0.1947(3) 0.22911(16) 0.07861(16) 0.0286(5) Uani 1 1 d . . . H14A H 0.1548 0.1599 0.0980 0.034 Uiso 1 1 calc R . . H14B H 0.2188 0.2389 0.0039 0.034 Uiso 1 1 calc R . . C15 C 0.5163(3) 0.18776(15) 0.07972(15) 0.0247(4) Uani 1 1 d . . . C16 C 0.6106(3) 0.24938(16) 0.00311(16) 0.0289(5) Uani 1 1 d . . . C17 C 0.7571(3) 0.20132(18) -0.04984(16) 0.0340(5) Uani 1 1 d . . . H17 H 0.8213 0.2416 -0.1005 0.041 Uiso 1 1 calc R . . C18 C 0.8080(3) 0.09469(18) -0.02800(17) 0.0360(5) Uani 1 1 d . . . H18 H 0.9055 0.0630 -0.0642 0.043 Uiso 1 1 calc R . . C19 C 0.7142(3) 0.03515(17) 0.04755(17) 0.0339(5) Uani 1 1 d . . . H19 H 0.7492 -0.0369 0.0615 0.041 Uiso 1 1 calc R . . C20 C 0.5687(3) 0.07972(16) 0.10353(16) 0.0277(4) Uani 1 1 d . . . C21 C 0.5572(3) 0.36621(17) -0.02079(18) 0.0401(6) Uani 1 1 d . . . H21A H 0.6364 0.3955 -0.0748 0.060 Uiso 1 1 calc R . . H21B H 0.5649 0.3991 0.0407 0.060 Uiso 1 1 calc R . . H21C H 0.4362 0.3785 -0.0435 0.060 Uiso 1 1 calc R . . C22 C 0.4752(3) 0.01467(16) 0.18937(18) 0.0361(5) Uani 1 1 d . . . H22A H 0.5268 -0.0576 0.1932 0.054 Uiso 1 1 calc R . . H22B H 0.3499 0.0194 0.1759 0.054 Uiso 1 1 calc R . . H22C H 0.4888 0.0404 0.2542 0.054 Uiso 1 1 calc R . . C23 C 0.3221(4) 0.2793(2) 0.7548(2) 0.0515(7) Uani 1 1 d . . . C24 C 0.5006(3) 0.2908(2) 0.7100(2) 0.0512(7) Uani 1 1 d . . . H24A H 0.5007 0.2897 0.6361 0.077 Uiso 1 1 calc R . . H24B H 0.5833 0.2338 0.7403 0.077 Uiso 1 1 calc R . . H24C H 0.5363 0.3567 0.7236 0.077 Uiso 1 1 calc R . . N5 N 0.1826(4) 0.2695(3) 0.7892(2) 0.0829(9) 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 Fe1 0.01947(16) 0.02657(17) 0.02471(17) -0.00389(12) -0.00332(11) -0.00300(11) Cl1 0.0279(3) 0.0475(3) 0.0434(3) 0.0002(3) -0.0147(2) -0.0065(2) Cl2 0.0402(3) 0.0292(3) 0.0273(3) -0.0071(2) 0.0031(2) -0.0109(2) N1 0.0245(9) 0.0247(8) 0.0249(9) -0.0050(7) -0.0003(7) -0.0062(7) N2 0.0213(8) 0.0243(8) 0.0222(9) -0.0033(7) -0.0011(7) -0.0017(7) N3 0.0226(8) 0.0274(9) 0.0234(9) -0.0039(7) -0.0007(7) -0.0031(7) N4 0.0237(9) 0.0294(9) 0.0266(9) -0.0088(7) -0.0016(7) -0.0028(7) C1 0.0302(11) 0.0272(11) 0.0276(11) -0.0028(9) -0.0013(9) -0.0106(9) C2 0.0420(13) 0.0362(12) 0.0254(11) -0.0088(9) 0.0069(10) -0.0171(10) C3 0.0315(12) 0.0356(12) 0.0410(14) -0.0142(10) 0.0124(10) -0.0088(10) C4 0.0240(11) 0.0301(11) 0.0403(13) -0.0087(10) 0.0036(9) -0.0024(9) C5 0.0240(10) 0.0238(10) 0.0278(11) -0.0049(8) 0.0005(8) -0.0054(8) C6 0.0243(10) 0.0285(10) 0.0287(11) -0.0051(9) -0.0038(8) 0.0038(8) C7 0.0230(10) 0.0307(11) 0.0303(11) -0.0055(9) -0.0045(8) -0.0045(8) C8 0.0241(10) 0.0295(11) 0.0229(10) -0.0036(8) -0.0006(8) -0.0047(8) C9 0.0384(13) 0.0380(13) 0.0430(14) 0.0007(11) -0.0126(10) -0.0149(10) C10 0.0544(16) 0.0320(12) 0.0556(17) 0.0064(11) -0.0125(13) -0.0166(11) C11 0.0406(13) 0.0319(12) 0.0404(14) 0.0064(10) -0.0041(10) -0.0026(10) C12 0.0268(11) 0.0375(12) 0.0257(11) -0.0011(9) -0.0039(9) -0.0034(9) C13 0.0265(11) 0.0346(11) 0.0233(11) -0.0036(9) -0.0051(8) 0.0003(9) C14 0.0268(11) 0.0372(12) 0.0231(11) -0.0091(9) -0.0026(8) -0.0020(9) C15 0.0233(10) 0.0296(10) 0.0231(11) -0.0079(8) -0.0030(8) -0.0046(8) C16 0.0308(11) 0.0328(11) 0.0241(11) -0.0052(9) -0.0029(9) -0.0052(9) C17 0.0309(12) 0.0487(14) 0.0244(11) -0.0071(10) 0.0008(9) -0.0107(10) C18 0.0261(11) 0.0482(14) 0.0353(13) -0.0179(11) -0.0009(9) 0.0028(10) C19 0.0307(12) 0.0326(12) 0.0397(13) -0.0113(10) -0.0055(10) 0.0006(9) C20 0.0243(10) 0.0304(11) 0.0304(11) -0.0085(9) -0.0051(9) -0.0045(8) C21 0.0491(14) 0.0359(12) 0.0333(13) 0.0023(10) 0.0046(11) -0.0071(11) C22 0.0346(12) 0.0295(11) 0.0426(14) -0.0006(10) -0.0012(10) -0.0022(9) C23 0.0614(18) 0.0587(17) 0.0338(14) 0.0036(12) -0.0120(13) -0.0101(14) C24 0.0577(17) 0.0505(15) 0.0460(16) -0.0002(12) -0.0057(13) -0.0141(13) N5 0.0604(17) 0.140(3) 0.0473(16) 0.0011(16) -0.0024(13) -0.0215(17) _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 Fe1 N1 2.1712(16) . ? Fe1 N3 2.1883(16) . ? Fe1 N2 2.2636(16) . ? Fe1 Cl1 2.3203(6) . ? Fe1 Cl2 2.4627(6) . ? N1 C1 1.340(2) . ? N1 C5 1.342(2) . ? N2 C6 1.477(2) . ? N2 C13 1.481(2) . ? N2 C7 1.487(2) . ? N3 C8 1.337(2) . ? N3 C12 1.343(2) . ? N4 C15 1.444(2) . ? N4 C14 1.482(2) . ? C1 C2 1.375(3) . ? C2 C3 1.371(3) . ? C3 C4 1.375(3) . ? C4 C5 1.382(3) . ? C5 C6 1.497(3) . ? C7 C8 1.504(3) . ? C8 C9 1.377(3) . ? C9 C10 1.375(3) . ? C10 C11 1.379(3) . ? C11 C12 1.367(3) . ? C13 C14 1.506(3) . ? C15 C20 1.398(3) . ? C15 C16 1.400(3) . ? C16 C17 1.390(3) . ? C16 C21 1.505(3) . ? C17 C18 1.376(3) . ? C18 C19 1.375(3) . ? C19 C20 1.387(3) . ? C20 C22 1.494(3) . ? C23 N5 1.129(3) . ? C23 C24 1.446(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 N1 Fe1 N3 91.02(6) . . ? N1 Fe1 N2 74.91(6) . . ? N3 Fe1 N2 77.81(6) . . ? N1 Fe1 Cl1 103.12(5) . . ? N3 Fe1 Cl1 93.68(5) . . ? N2 Fe1 Cl1 171.15(4) . . ? N1 Fe1 Cl2 92.72(4) . . ? N3 Fe1 Cl2 167.38(5) . . ? N2 Fe1 Cl2 91.53(4) . . ? Cl1 Fe1 Cl2 97.20(2) . . ? C1 N1 C5 117.90(17) . . ? C1 N1 Fe1 125.77(13) . . ? C5 N1 Fe1 116.32(13) . . ? C6 N2 C13 109.86(14) . . ? C6 N2 C7 109.43(15) . . ? C13 N2 C7 111.04(15) . . ? C6 N2 Fe1 105.63(11) . . ? C13 N2 Fe1 111.09(11) . . ? C7 N2 Fe1 109.64(11) . . ? C8 N3 C12 117.81(17) . . ? C8 N3 Fe1 116.13(13) . . ? C12 N3 Fe1 125.57(13) . . ? C15 N4 C14 110.93(14) . . ? N1 C1 C2 122.88(19) . . ? C3 C2 C1 118.7(2) . . ? C2 C3 C4 119.45(19) . . ? C3 C4 C5 118.8(2) . . ? N1 C5 C4 122.27(19) . . ? N1 C5 C6 115.83(16) . . ? C4 C5 C6 121.86(18) . . ? N2 C6 C5 110.34(15) . . ? N2 C7 C8 114.42(15) . . ? N3 C8 C9 122.08(18) . . ? N3 C8 C7 117.80(17) . . ? C9 C8 C7 120.00(18) . . ? C10 C9 C8 119.4(2) . . ? C9 C10 C11 118.9(2) . . ? C12 C11 C10 118.5(2) . . ? N3 C12 C11 123.24(19) . . ? N2 C13 C14 111.52(16) . . ? N4 C14 C13 109.34(15) . . ? C20 C15 C16 120.80(18) . . ? C20 C15 N4 119.78(18) . . ? C16 C15 N4 119.40(17) . . ? C17 C16 C15 118.96(19) . . ? C17 C16 C21 120.15(19) . . ? C15 C16 C21 120.88(18) . . ? C18 C17 C16 120.6(2) . . ? C19 C18 C17 119.8(2) . . ? C18 C19 C20 121.7(2) . . ? C19 C20 C15 118.07(19) . . ? C19 C20 C22 120.81(19) . . ? C15 C20 C22 121.08(18) . . ? N5 C23 C24 179.3(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.366 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.058