# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Julia Klingele' _publ_contact_author_email JULIA.KLINGELE@AC.UNI-FREIBURG.DE _publ_section_title ; Triazolopyridines as ligands: structural diversity in iron(II), cobalt(II), nickel(II) and copper(II) complexes of 3-(2-pyridyl)-[1,2,4]triazolo[4,3-a]pyridine (L10) and spin crossover in [FeII(L10)2(NCS)2] ; loop_ _publ_author_name 'Julia Klingele' 'Jakob Hilgert' 'Dominik Kaase' 'Marco H. Klingele' 'Jochen Lach' 'Gunther Steinfeld' data_afp01 _database_code_depnum_ccdc_archive 'CCDC 755105' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C24 H24 Cu N8 O2, 2(Cl O4) ; _chemical_formula_sum 'C24 H24 Cl2 Cu N8 O10' _chemical_formula_weight 718.95 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 7.6849(14) _cell_length_b 7.6919(14) _cell_length_c 12.421(3) _cell_angle_alpha 86.877(4) _cell_angle_beta 83.017(5) _cell_angle_gamma 74.179(4) _cell_volume 701.0(2) _cell_formula_units_Z 1 _cell_measurement_temperature 155(2) _cell_measurement_reflns_used 2683 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 26.36 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.703 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 367 _exptl_absorpt_coefficient_mu 1.043 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7248 _exptl_absorpt_correction_T_max 0.9029 _exptl_absorpt_process_details ; March 2001 T Higashi ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 155(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 'Rigaku R-Axis SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4473 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0766 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 26.36 _reflns_number_total 2683 _reflns_number_gt 1884 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2683 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 Cu1 Cu 0.0000 0.5000 0.5000 0.0221(2) Uani 1 2 d S . . N1 N 0.1857(4) 0.3400(4) 0.3881(3) 0.0216(8) Uani 1 1 d . . . N2 N 0.0176(4) 0.6806(4) 0.3818(3) 0.0230(8) Uani 1 1 d . . . N3 N -0.0596(5) 0.8609(4) 0.3690(3) 0.0242(8) Uani 1 1 d . . . N4 N 0.1327(4) 0.7560(4) 0.2235(2) 0.0193(7) Uani 1 1 d . . . C1 C 0.2668(5) 0.1650(5) 0.4006(3) 0.0244(10) Uani 1 1 d . . . H1A H 0.2369 0.1047 0.4662 0.029 Uiso 1 1 calc R . . C2 C 0.3925(6) 0.0679(6) 0.3223(3) 0.0292(11) Uani 1 1 d . . . H2A H 0.4492 -0.0568 0.3341 0.035 Uiso 1 1 calc R . . C3 C 0.4349(6) 0.1546(6) 0.2261(3) 0.0305(11) Uani 1 1 d . . . H3A H 0.5194 0.0898 0.1703 0.037 Uiso 1 1 calc R . . C4 C 0.3527(6) 0.3365(6) 0.2125(3) 0.0270(10) Uani 1 1 d . . . H4A H 0.3803 0.3991 0.1474 0.032 Uiso 1 1 calc R . . C5 C 0.2289(5) 0.4263(5) 0.2956(3) 0.0202(9) Uani 1 1 d . . . C6 C 0.1312(5) 0.6165(5) 0.2969(3) 0.0184(9) Uani 1 1 d . . . C7 C 0.0098(5) 0.9065(5) 0.2726(3) 0.0224(9) Uani 1 1 d . . . C8 C -0.0199(6) 1.0754(6) 0.2184(3) 0.0265(10) Uani 1 1 d . . . H8A H -0.1030 1.1795 0.2506 0.032 Uiso 1 1 calc R . . C9 C 0.0724(6) 1.0865(6) 0.1194(3) 0.0274(10) Uani 1 1 d . . . H9A H 0.0560 1.1999 0.0820 0.033 Uiso 1 1 calc R . . C10 C 0.1935(6) 0.9297(6) 0.0710(3) 0.0295(10) Uani 1 1 d . . . H10A H 0.2555 0.9399 0.0009 0.035 Uiso 1 1 calc R . . C11 C 0.2226(6) 0.7680(6) 0.1214(3) 0.0269(10) Uani 1 1 d . . . H11A H 0.3032 0.6639 0.0878 0.032 Uiso 1 1 calc R . . O1 O 0.2367(3) 0.5689(3) 0.5771(2) 0.0345(8) Uani 1 1 d . . . H1 H 0.2781 0.5281 0.6424 0.041 Uiso 1 1 d R . . C12 C 0.3323(3) 0.6972(3) 0.5403(2) 0.0358(11) Uani 1 1 d R . . H12A H 0.4494 0.6663 0.5703 0.043 Uiso 1 1 calc R . . H12B H 0.2606 0.8176 0.5642 0.043 Uiso 1 1 calc R . . H12C H 0.3532 0.6971 0.4609 0.043 Uiso 1 1 calc R . . Cl1 Cl 0.28476(14) 0.38158(13) 0.85335(8) 0.0253(3) Uani 1 1 d . . . O11 O 0.2716(6) 0.2058(4) 0.8794(3) 0.0674(13) Uani 1 1 d . . . O12 O 0.4082(4) 0.3761(4) 0.7547(2) 0.0378(8) Uani 1 1 d . . . O13 O 0.3530(5) 0.4528(6) 0.9365(3) 0.0583(11) Uani 1 1 d . . . O14 O 0.1092(4) 0.4934(4) 0.8357(3) 0.0474(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 Cu1 0.0256(4) 0.0176(4) 0.0196(4) 0.0018(3) 0.0038(3) -0.0031(3) N1 0.0224(18) 0.0190(18) 0.0217(17) 0.0006(14) 0.0016(14) -0.0047(15) N2 0.0247(18) 0.0185(18) 0.0244(18) 0.0009(14) 0.0028(14) -0.0060(15) N3 0.0293(19) 0.0169(18) 0.0235(18) 0.0029(14) 0.0016(15) -0.0038(15) N4 0.0212(17) 0.0199(18) 0.0169(16) 0.0021(13) 0.0000(13) -0.0069(15) C1 0.027(2) 0.023(2) 0.023(2) 0.0015(17) -0.0019(17) -0.0067(18) C2 0.031(2) 0.019(2) 0.036(2) -0.0033(19) 0.003(2) -0.0056(19) C3 0.032(2) 0.028(2) 0.029(2) -0.0082(19) 0.0103(19) -0.008(2) C4 0.035(2) 0.025(2) 0.021(2) -0.0008(18) 0.0022(18) -0.010(2) C5 0.021(2) 0.022(2) 0.019(2) -0.0006(16) -0.0015(16) -0.0089(18) C6 0.0172(19) 0.020(2) 0.0191(19) 0.0005(16) -0.0008(16) -0.0080(17) C7 0.022(2) 0.022(2) 0.023(2) -0.0008(17) 0.0001(17) -0.0076(18) C8 0.027(2) 0.021(2) 0.030(2) 0.0022(18) 0.0003(18) -0.0048(19) C9 0.028(2) 0.027(2) 0.028(2) 0.0062(18) -0.0031(18) -0.0098(19) C10 0.036(3) 0.029(2) 0.022(2) 0.0073(18) 0.0040(19) -0.010(2) C11 0.026(2) 0.034(2) 0.018(2) -0.0002(18) 0.0062(17) -0.006(2) O1 0.0373(18) 0.044(2) 0.0318(17) 0.0136(15) -0.0114(14) -0.0258(16) C12 0.042(3) 0.032(3) 0.037(3) -0.001(2) -0.002(2) -0.017(2) Cl1 0.0280(6) 0.0217(6) 0.0253(5) 0.0012(4) -0.0029(4) -0.0054(4) O11 0.076(3) 0.0228(19) 0.088(3) 0.0150(19) 0.033(2) -0.0094(19) O12 0.0406(19) 0.045(2) 0.0275(17) 0.0004(14) 0.0019(14) -0.0132(16) O13 0.037(2) 0.105(3) 0.036(2) -0.030(2) -0.0053(16) -0.017(2) O14 0.0330(19) 0.043(2) 0.062(2) 0.0006(17) -0.0157(17) 0.0016(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.984(3) . ? Cu1 N2 1.984(3) 2_566 ? Cu1 N1 2.057(3) 2_566 ? Cu1 N1 2.057(3) . ? Cu1 O1 2.347(3) . ? Cu1 O1 2.347(3) 2_566 ? N1 C1 1.329(5) . ? N1 C5 1.348(5) . ? N2 C6 1.309(5) . ? N2 N3 1.360(4) . ? N3 C7 1.320(5) . ? N4 C6 1.372(5) . ? N4 C11 1.379(5) . ? N4 C7 1.395(5) . ? C1 C2 1.377(5) . ? C1 H1A 0.9500 . ? C2 C3 1.384(6) . ? C2 H2A 0.9500 . ? C3 C4 1.380(6) . ? C3 H3A 0.9500 . ? C4 C5 1.389(5) . ? C4 H4A 0.9500 . ? C5 C6 1.450(5) . ? C7 C8 1.404(6) . ? C8 C9 1.354(6) . ? C8 H8A 0.9500 . ? C9 C10 1.419(6) . ? C9 H9A 0.9500 . ? C10 C11 1.337(6) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? O1 C12 1.4095 . ? O1 H1 0.9164 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? Cl1 O11 1.401(3) . ? Cl1 O13 1.411(3) . ? Cl1 O14 1.424(3) . ? Cl1 O12 1.451(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N2 180.0 . 2_566 ? N2 Cu1 N1 100.38(13) . 2_566 ? N2 Cu1 N1 79.62(13) 2_566 2_566 ? N2 Cu1 N1 79.62(13) . . ? N2 Cu1 N1 100.38(13) 2_566 . ? N1 Cu1 N1 180.00(17) 2_566 . ? N2 Cu1 O1 89.92(12) . . ? N2 Cu1 O1 90.08(12) 2_566 . ? N1 Cu1 O1 89.55(12) 2_566 . ? N1 Cu1 O1 90.45(12) . . ? N2 Cu1 O1 90.08(12) . 2_566 ? N2 Cu1 O1 89.93(12) 2_566 2_566 ? N1 Cu1 O1 90.45(12) 2_566 2_566 ? N1 Cu1 O1 89.55(12) . 2_566 ? O1 Cu1 O1 180.0 . 2_566 ? C1 N1 C5 118.9(3) . . ? C1 N1 Cu1 126.1(3) . . ? C5 N1 Cu1 115.0(2) . . ? C6 N2 N3 111.1(3) . . ? C6 N2 Cu1 114.5(3) . . ? N3 N2 Cu1 134.3(2) . . ? C7 N3 N2 105.8(3) . . ? C6 N4 C11 133.8(3) . . ? C6 N4 C7 104.7(3) . . ? C11 N4 C7 121.5(3) . . ? N1 C1 C2 122.5(4) . . ? N1 C1 H1A 118.7 . . ? C2 C1 H1A 118.7 . . ? C1 C2 C3 119.0(4) . . ? C1 C2 H2A 120.5 . . ? C3 C2 H2A 120.5 . . ? C4 C3 C2 119.0(4) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 118.8(4) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? N1 C5 C4 121.7(4) . . ? N1 C5 C6 111.4(3) . . ? C4 C5 C6 126.9(4) . . ? N2 C6 N4 108.2(3) . . ? N2 C6 C5 119.4(3) . . ? N4 C6 C5 132.4(3) . . ? N3 C7 N4 110.2(3) . . ? N3 C7 C8 130.3(4) . . ? N4 C7 C8 119.5(3) . . ? C9 C8 C7 118.5(4) . . ? C9 C8 H8A 120.7 . . ? C7 C8 H8A 120.7 . . ? C8 C9 C10 120.4(4) . . ? C8 C9 H9A 119.8 . . ? C10 C9 H9A 119.8 . . ? C11 C10 C9 121.7(4) . . ? C11 C10 H10A 119.2 . . ? C9 C10 H10A 119.2 . . ? C10 C11 N4 118.4(4) . . ? C10 C11 H11A 120.8 . . ? N4 C11 H11A 120.8 . . ? C12 O1 H1 104.2 . . ? Cu1 O1 H1 127.3 . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O11 Cl1 O13 111.6(3) . . ? O11 Cl1 O14 108.8(2) . . ? O13 Cl1 O14 109.8(2) . . ? O11 Cl1 O12 108.4(2) . . ? O13 Cl1 O12 108.6(2) . . ? O14 Cl1 O12 109.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 N1 C1 178.7(4) . . . . ? N2 Cu1 N1 C1 -1.3(4) 2_566 . . . ? O1 Cu1 N1 C1 88.9(3) . . . . ? O1 Cu1 N1 C1 -91.1(3) 2_566 . . . ? N2 Cu1 N1 C5 0.4(3) . . . . ? N2 Cu1 N1 C5 -179.6(3) 2_566 . . . ? O1 Cu1 N1 C5 -89.4(3) . . . . ? O1 Cu1 N1 C5 90.6(3) 2_566 . . . ? N1 Cu1 N2 C6 179.3(3) 2_566 . . . ? N1 Cu1 N2 C6 -0.7(3) . . . . ? O1 Cu1 N2 C6 89.8(3) . . . . ? O1 Cu1 N2 C6 -90.2(3) 2_566 . . . ? N1 Cu1 N2 N3 1.2(4) 2_566 . . . ? N1 Cu1 N2 N3 -178.8(4) . . . . ? O1 Cu1 N2 N3 -88.4(4) . . . . ? O1 Cu1 N2 N3 91.6(4) 2_566 . . . ? C6 N2 N3 C7 0.2(5) . . . . ? Cu1 N2 N3 C7 178.4(3) . . . . ? C5 N1 C1 C2 -0.6(6) . . . . ? Cu1 N1 C1 C2 -178.8(3) . . . . ? N1 C1 C2 C3 -0.8(7) . . . . ? C1 C2 C3 C4 1.3(7) . . . . ? C2 C3 C4 C5 -0.5(7) . . . . ? C1 N1 C5 C4 1.4(6) . . . . ? Cu1 N1 C5 C4 179.8(3) . . . . ? C1 N1 C5 C6 -178.6(4) . . . . ? Cu1 N1 C5 C6 -0.1(4) . . . . ? C3 C4 C5 N1 -0.9(6) . . . . ? C3 C4 C5 C6 179.1(4) . . . . ? N3 N2 C6 N4 0.0(4) . . . . ? Cu1 N2 C6 N4 -178.6(2) . . . . ? N3 N2 C6 C5 179.4(3) . . . . ? Cu1 N2 C6 C5 0.8(5) . . . . ? C11 N4 C6 N2 -179.1(4) . . . . ? C7 N4 C6 N2 -0.2(4) . . . . ? C11 N4 C6 C5 1.6(7) . . . . ? C7 N4 C6 C5 -179.5(4) . . . . ? N1 C5 C6 N2 -0.5(5) . . . . ? C4 C5 C6 N2 179.6(4) . . . . ? N1 C5 C6 N4 178.8(4) . . . . ? C4 C5 C6 N4 -1.1(7) . . . . ? N2 N3 C7 N4 -0.4(4) . . . . ? N2 N3 C7 C8 -179.2(4) . . . . ? C6 N4 C7 N3 0.4(4) . . . . ? C11 N4 C7 N3 179.4(4) . . . . ? C6 N4 C7 C8 179.3(4) . . . . ? C11 N4 C7 C8 -1.7(6) . . . . ? N3 C7 C8 C9 178.8(4) . . . . ? N4 C7 C8 C9 0.0(6) . . . . ? C7 C8 C9 C10 1.3(6) . . . . ? C8 C9 C10 C11 -1.0(7) . . . . ? C9 C10 C11 N4 -0.6(7) . . . . ? C6 N4 C11 C10 -179.4(4) . . . . ? C7 N4 C11 C10 1.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 0.555 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.095 data_afp02 _database_code_depnum_ccdc_archive 'CCDC 755106' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C22 H16 Cl2 Cu N8 O8 ; _chemical_formula_sum 'C22 H16 Cl2 Cu N8 O8' _chemical_formula_weight 654.87 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 7.3805(15) _cell_length_b 9.0684(18) _cell_length_c 9.782(2) _cell_angle_alpha 92.54(3) _cell_angle_beta 108.65(3) _cell_angle_gamma 103.41(3) _cell_volume 598.4(2) _cell_formula_units_Z 1 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2737 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.817 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 331 _exptl_absorpt_coefficient_mu 1.206 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6776 _exptl_absorpt_correction_T_max 0.7445 _exptl_absorpt_process_details ; March 2001 T Higashi ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Rigaku R-Axis SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16743 _diffrn_reflns_av_R_equivalents 0.0658 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2737 _reflns_number_gt 2254 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+0.3057P] 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 2737 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 Cu1 Cu 0.5000 0.0000 0.5000 0.01475(13) Uani 1 2 d S . . N2 N 0.7166(3) 0.1441(2) 0.4580(2) 0.0163(4) Uani 1 1 d . . . N3 N 0.9170(3) 0.1866(2) 0.5196(2) 0.0168(4) Uani 1 1 d . . . N4 N 0.8198(3) 0.3144(2) 0.3299(2) 0.0150(4) Uani 1 1 d . . . N1 N 0.3364(3) 0.0873(2) 0.3281(2) 0.0155(4) Uani 1 1 d . . . C1 C 0.1387(4) 0.0508(3) 0.2682(2) 0.0168(5) Uani 1 1 d . . . H1A H 0.0623 -0.0205 0.3098 0.020 Uiso 1 1 calc R . . C2 C 0.0408(4) 0.1127(3) 0.1478(3) 0.0188(5) Uani 1 1 d . . . H2A H -0.0998 0.0848 0.1081 0.023 Uiso 1 1 calc R . . C3 C 0.1517(4) 0.2156(3) 0.0870(3) 0.0205(5) Uani 1 1 d . . . H3A H 0.0876 0.2587 0.0040 0.025 Uiso 1 1 calc R . . C4 C 0.35702(16) 0.25645(12) 0.14686(11) 0.0182(5) Uani 1 1 d . . . H4A H 0.4351 0.3276 0.1063 0.022 Uiso 1 1 calc R . . C5 C 0.44473(16) 0.19057(12) 0.26731(11) 0.0148(5) Uani 1 1 d R . . C6 C 0.65666(16) 0.21893(12) 0.34557(11) 0.0148(5) Uani 1 1 d R . . C7 C 0.98016(16) 0.29111(12) 0.44236(11) 0.0165(5) Uani 1 1 d R . . C8 C 1.17557(16) 0.37637(12) 0.46241(11) 0.0180(5) Uani 1 1 d R . . H8A H 1.2856 0.3617 0.5384 0.022 Uiso 1 1 calc R . . C9 C 1.2006(4) 0.4802(3) 0.3691(3) 0.0206(5) Uani 1 1 d . . . H9A H 1.3301 0.5390 0.3800 0.025 Uiso 1 1 calc R . . C10 C 1.0347(4) 0.5016(3) 0.2551(3) 0.0209(5) Uani 1 1 d . . . H10A H 1.0563 0.5748 0.1915 0.025 Uiso 1 1 calc R . . C11 C 0.8483(4) 0.4210(3) 0.2351(3) 0.0192(5) Uani 1 1 d . . . H11A H 0.7393 0.4363 0.1586 0.023 Uiso 1 1 calc R . . Cl1 Cl 0.50691(8) 0.21953(6) 0.81703(6) 0.01715(15) Uani 1 1 d . . . O11 O 0.5007(3) 0.21049(19) 0.66667(18) 0.0228(4) Uani 1 1 d . . . O12 O 0.3658(3) 0.0921(2) 0.8338(2) 0.0408(5) Uani 1 1 d . . . O13 O 0.4669(4) 0.3606(2) 0.8540(2) 0.0439(6) Uani 1 1 d . . . O14 O 0.7007(3) 0.2181(3) 0.9084(2) 0.0479(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0140(2) 0.0167(2) 0.0135(2) 0.00601(15) 0.00448(17) 0.00359(16) N2 0.0159(10) 0.0177(10) 0.0149(9) 0.0046(8) 0.0040(8) 0.0050(8) N3 0.0127(10) 0.0196(10) 0.0170(10) 0.0047(8) 0.0048(8) 0.0020(8) N4 0.0161(10) 0.0163(10) 0.0145(9) 0.0037(8) 0.0066(8) 0.0053(8) N1 0.0175(10) 0.0158(10) 0.0140(9) 0.0033(8) 0.0064(8) 0.0042(8) C1 0.0177(12) 0.0166(11) 0.0175(11) 0.0022(9) 0.0080(10) 0.0041(9) C2 0.0172(13) 0.0220(12) 0.0152(11) 0.0009(9) 0.0029(10) 0.0057(10) C3 0.0231(13) 0.0247(13) 0.0141(11) 0.0068(10) 0.0045(10) 0.0090(10) C4 0.0213(13) 0.0204(12) 0.0141(11) 0.0050(9) 0.0072(10) 0.0055(10) C5 0.0170(12) 0.0153(11) 0.0127(11) 0.0003(9) 0.0055(10) 0.0050(9) C6 0.0163(12) 0.0152(11) 0.0140(11) 0.0021(9) 0.0066(10) 0.0041(9) C7 0.0196(12) 0.0191(12) 0.0143(11) 0.0041(9) 0.0079(10) 0.0085(10) C8 0.0151(12) 0.0203(12) 0.0181(11) 0.0026(9) 0.0044(10) 0.0053(10) C9 0.0202(13) 0.0198(12) 0.0237(13) 0.0027(10) 0.0106(11) 0.0041(10) C10 0.0232(14) 0.0197(12) 0.0224(12) 0.0075(10) 0.0111(11) 0.0048(10) C11 0.0233(13) 0.0201(12) 0.0185(12) 0.0086(10) 0.0096(11) 0.0091(10) Cl1 0.0201(3) 0.0182(3) 0.0138(3) 0.0043(2) 0.0064(2) 0.0050(2) O11 0.0329(11) 0.0216(9) 0.0171(9) 0.0043(7) 0.0117(8) 0.0084(8) O12 0.0473(13) 0.0364(12) 0.0378(12) 0.0038(9) 0.0276(11) -0.0091(10) O13 0.0857(18) 0.0319(12) 0.0345(12) 0.0107(9) 0.0339(12) 0.0338(12) O14 0.0323(12) 0.0695(17) 0.0302(12) 0.0066(11) -0.0059(10) 0.0143(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.983(2) . ? Cu1 N2 1.983(2) 2_656 ? Cu1 N1 2.043(2) . ? Cu1 N1 2.043(2) 2_656 ? N2 N3 1.358(3) . ? N4 C11 1.397(3) . ? N1 C1 1.340(3) . ? C1 C2 1.389(3) . ? C1 H1A 0.9500 . ? C2 C3 1.379(3) . ? C2 H2A 0.9500 . ? C3 C4 1.389(3) . ? C3 H3A 0.9500 . ? C4 C5 1.3850 . ? C4 H4A 0.9500 . ? C5 C6 1.4591 . ? C7 C8 1.4159 . ? C8 H8A 0.9500 . ? C9 C10 1.427(4) . ? C9 H9A 0.9500 . ? C10 C11 1.346(3) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? Cl1 O12 1.419(2) . ? Cl1 O14 1.427(2) . ? Cl1 O13 1.435(2) . ? Cl1 O11 1.4548(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 N2 Cu1 N2 180.00(10) . 2_656 ? N2 Cu1 N1 80.34(8) . . ? N2 Cu1 N1 99.66(8) 2_656 . ? N2 Cu1 N1 99.66(8) . 2_656 ? N2 Cu1 N1 80.34(8) 2_656 2_656 ? N1 Cu1 N1 180.0 . 2_656 ? N3 N2 Cu1 134.55(15) . . ? C1 N1 Cu1 126.95(16) . . ? N1 C1 C2 122.7(2) . . ? N1 C1 H1A 118.6 . . ? C2 C1 H1A 118.6 . . ? C3 C2 C1 118.6(2) . . ? C3 C2 H2A 120.7 . . ? C1 C2 H2A 120.7 . . ? C2 C3 C4 120.1(2) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 H4A 120.9 . . ? C3 C4 H4A 120.9 . . ? C4 C5 C6 126.4 . . ? C9 C8 H8A 121.1 . . ? C7 C8 H8A 121.1 . . ? C8 C9 H9A 119.6 . . ? C10 C9 H9A 119.6 . . ? C11 C10 C9 121.8(2) . . ? C11 C10 H10A 119.1 . . ? C9 C10 H10A 119.1 . . ? C10 C11 N4 118.2(2) . . ? C10 C11 H11A 120.9 . . ? N4 C11 H11A 120.9 . . ? O12 Cl1 O14 109.59(15) . . ? O12 Cl1 O13 111.19(14) . . ? O14 Cl1 O13 109.20(15) . . ? O12 Cl1 O11 109.61(12) . . ? O14 Cl1 O11 108.66(13) . . ? O13 Cl1 O11 108.55(11) . . ? 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 N1 Cu1 N2 N3 177.6(2) . . . . ? N1 Cu1 N2 N3 -2.4(2) 2_656 . . . ? N2 Cu1 N1 C1 -179.9(2) . . . . ? N2 Cu1 N1 C1 0.1(2) 2_656 . . . ? Cu1 N1 C1 C2 -177.67(17) . . . . ? N1 C1 C2 C3 0.3(4) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C7 N4 C6 C5 178.1 . . . . ? C8 C9 C10 C11 0.0(4) . . . . ? C9 C10 C11 N4 0.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.474 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.083 data_afp03_1 _database_code_depnum_ccdc_archive 'CCDC 755107' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C24 H24 Co N8 O2, 2(Cl O4) ; _chemical_formula_sum 'C24 H24 Cl2 Co N8 O10' _chemical_formula_weight 714.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 7.9270(16) _cell_length_b 12.265(3) _cell_length_c 15.141(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.32(3) _cell_angle_gamma 90.00 _cell_volume 1426.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 3252 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 27.46 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 730 _exptl_absorpt_coefficient_mu 0.861 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6929 _exptl_absorpt_correction_T_max 0.8332 _exptl_absorpt_process_details ; March 2001 T Higashi ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 'Rigaku R-Axis SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23628 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3252 _reflns_number_gt 2507 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.8464P] 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 3252 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0945 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 0.0000 1.0000 0.0000 0.02669(13) Uani 1 2 d S . . N1 N -0.1207(2) 1.15380(16) 0.01064(12) 0.0298(4) Uani 1 1 d . . . N2 N 0.1212(2) 1.10426(16) -0.07492(12) 0.0299(4) Uani 1 1 d . . . N3 N 0.2533(2) 1.09271(17) -0.11772(13) 0.0352(5) Uani 1 1 d . . . N4 N 0.1707(2) 1.26717(16) -0.12099(12) 0.0294(4) Uani 1 1 d . . . C1 C -0.2494(3) 1.1711(2) 0.05253(17) 0.0378(5) Uani 1 1 d . . . H1 H -0.2839 1.1132 0.0848 0.045 Uiso 1 1 calc R . . C2 C -0.3328(3) 1.2702(2) 0.05006(18) 0.0433(6) Uani 1 1 d . . . H2 H -0.4203 1.2801 0.0814 0.052 Uiso 1 1 calc R . . C3 C -0.2859(3) 1.3540(2) 0.00113(19) 0.0431(6) Uani 1 1 d . . . H3 H -0.3434 1.4216 -0.0027 0.052 Uiso 1 1 calc R . . C4 C -0.1531(3) 1.3385(2) -0.04269(17) 0.0378(5) Uani 1 1 d . . . H4 H -0.1192 1.3952 -0.0764 0.045 Uiso 1 1 calc R . . C5 C -0.0717(3) 1.23815(19) -0.03567(14) 0.0281(5) Uani 1 1 d . . . C6 C 0.0709(3) 1.20666(18) -0.07663(14) 0.0268(4) Uani 1 1 d . . . C7 C 0.2820(3) 1.1921(2) -0.14603(15) 0.0327(5) Uani 1 1 d . . . C8 C 0.4033(3) 1.2280(2) -0.19476(17) 0.0425(6) Uani 1 1 d . . . H8 H 0.4774 1.1781 -0.2136 0.051 Uiso 1 1 calc R . . C9 C 0.4101(4) 1.3347(3) -0.21342(18) 0.0480(7) Uani 1 1 d . . . H9 H 0.4896 1.3596 -0.2458 0.058 Uiso 1 1 calc R . . C10 C 0.2989(3) 1.4106(2) -0.18499(18) 0.0461(6) Uani 1 1 d . . . H10 H 0.3075 1.4850 -0.1979 0.055 Uiso 1 1 calc R . . C11 C 0.1810(3) 1.3776(2) -0.13965(17) 0.0384(6) Uani 1 1 d . . . H11 H 0.1075 1.4282 -0.1212 0.046 Uiso 1 1 calc R . . O20 O 0.1949(2) 1.02899(16) 0.11898(13) 0.0416(5) Uani 1 1 d . . . H20 H 0.186(4) 1.005(2) 0.161(2) 0.045(9) Uiso 1 1 d . . . C21 C 0.3682(3) 1.0639(3) 0.1242(2) 0.0561(8) Uani 1 1 d . . . H21A H 0.4322 1.0055 0.1039 0.084 Uiso 1 1 calc R . . H21B H 0.4248 1.0828 0.1867 0.084 Uiso 1 1 calc R . . H21C H 0.3659 1.1272 0.0855 0.084 Uiso 1 1 calc R . . Cl1 Cl 0.23831(8) 0.87468(5) 0.33218(4) 0.03770(16) Uani 1 1 d . . . O1 O 0.2213(3) 0.8786(2) 0.42295(14) 0.0778(8) Uani 1 1 d . A . O2 O 0.0617(6) 0.8552(7) 0.2838(4) 0.082(2) Uani 0.505(9) 1 d P A 1 O3 O 0.2930(14) 0.9710(5) 0.2992(4) 0.095(4) Uani 0.505(9) 1 d P A 1 O4 O 0.3380(9) 0.7831(5) 0.3317(5) 0.077(2) Uani 0.505(9) 1 d P A 1 O5 O 0.4115(7) 0.9196(6) 0.3361(4) 0.072(2) Uani 0.495(9) 1 d P A 2 O6 O 0.2313(12) 0.7756(5) 0.2773(6) 0.090(3) Uani 0.495(9) 1 d P A 2 O7 O 0.1189(10) 0.9448(9) 0.2771(4) 0.105(4) Uani 0.495(9) 1 d P A 2 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 0.0254(2) 0.0286(2) 0.0281(2) 0.00069(17) 0.01055(16) 0.00038(17) N1 0.0279(9) 0.0323(11) 0.0314(9) -0.0006(8) 0.0115(7) 0.0002(8) N2 0.0298(9) 0.0330(11) 0.0303(9) -0.0005(8) 0.0136(8) 0.0004(8) N3 0.0338(10) 0.0388(12) 0.0388(11) 0.0015(9) 0.0197(9) 0.0009(9) N4 0.0308(9) 0.0336(11) 0.0241(8) 0.0027(8) 0.0074(7) -0.0030(8) C1 0.0372(13) 0.0393(14) 0.0422(13) -0.0002(11) 0.0198(10) 0.0009(11) C2 0.0375(13) 0.0461(16) 0.0522(15) -0.0091(12) 0.0222(12) 0.0020(12) C3 0.0336(13) 0.0373(15) 0.0588(16) -0.0067(12) 0.0122(11) 0.0070(11) C4 0.0320(12) 0.0347(14) 0.0465(14) 0.0024(11) 0.0092(10) 0.0026(10) C5 0.0252(10) 0.0314(12) 0.0271(10) -0.0017(9) 0.0050(8) 0.0005(9) C6 0.0245(10) 0.0307(12) 0.0254(10) 0.0008(8) 0.0064(8) -0.0016(9) C7 0.0322(11) 0.0399(14) 0.0278(11) -0.0010(9) 0.0104(9) -0.0020(10) C8 0.0420(14) 0.0532(17) 0.0379(13) 0.0025(12) 0.0205(11) -0.0049(12) C9 0.0457(15) 0.0624(19) 0.0406(14) 0.0098(13) 0.0196(12) -0.0114(13) C10 0.0510(15) 0.0435(16) 0.0443(14) 0.0120(12) 0.0127(12) -0.0086(13) C11 0.0433(14) 0.0333(13) 0.0381(13) 0.0067(10) 0.0094(10) -0.0001(11) O20 0.0375(9) 0.0521(12) 0.0321(9) 0.0038(8) 0.0025(8) -0.0101(8) C21 0.0296(13) 0.070(2) 0.0623(18) 0.0069(16) -0.0008(12) -0.0048(13) Cl1 0.0412(3) 0.0373(3) 0.0341(3) 0.0027(2) 0.0085(2) -0.0020(3) O1 0.0653(14) 0.131(2) 0.0408(11) 0.0264(13) 0.0206(10) 0.0024(14) O2 0.050(3) 0.128(6) 0.049(3) -0.009(3) -0.020(2) -0.008(3) O3 0.180(11) 0.066(4) 0.044(3) -0.006(3) 0.039(4) -0.070(5) O4 0.089(5) 0.078(4) 0.072(4) -0.002(3) 0.032(3) 0.044(3) O5 0.048(3) 0.117(6) 0.059(4) -0.018(3) 0.027(3) -0.032(3) O6 0.130(7) 0.064(4) 0.087(5) -0.028(3) 0.045(5) -0.027(4) O7 0.088(5) 0.164(9) 0.076(4) 0.073(5) 0.045(4) 0.077(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 Co1 O20 2.0932(19) 3_575 ? Co1 O20 2.0932(19) . ? Co1 N2 2.0937(18) . ? Co1 N2 2.0938(18) 3_575 ? Co1 N1 2.1393(19) . ? Co1 N1 2.1393(19) 3_575 ? N1 C1 1.344(3) . ? N1 C5 1.360(3) . ? N2 C6 1.316(3) . ? N2 N3 1.369(2) . ? N3 C7 1.330(3) . ? N4 C6 1.375(3) . ? N4 C11 1.390(3) . ? N4 C7 1.391(3) . ? C1 C2 1.380(4) . ? C1 H1 0.9400 . ? C2 C3 1.371(4) . ? C2 H2 0.9400 . ? C3 C4 1.390(3) . ? C3 H3 0.9400 . ? C4 C5 1.382(3) . ? C4 H4 0.9400 . ? C5 C6 1.469(3) . ? C7 C8 1.419(3) . ? C8 C9 1.344(4) . ? C8 H8 0.9400 . ? C9 C10 1.419(4) . ? C9 H9 0.9400 . ? C10 C11 1.351(3) . ? C10 H10 0.9400 . ? C11 H11 0.9400 . ? O20 C21 1.423(3) . ? O20 H20 0.72(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? Cl1 O4 1.374(5) . ? Cl1 O3 1.393(4) . ? Cl1 O7 1.393(5) . ? Cl1 O1 1.415(2) . ? Cl1 O2 1.431(5) . ? Cl1 O6 1.465(6) . ? Cl1 O5 1.467(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 O20 Co1 O20 180.0 3_575 . ? O20 Co1 N2 88.70(8) 3_575 . ? O20 Co1 N2 91.30(8) . . ? O20 Co1 N2 91.30(8) 3_575 3_575 ? O20 Co1 N2 88.70(8) . 3_575 ? N2 Co1 N2 180.0 . 3_575 ? O20 Co1 N1 88.05(8) 3_575 . ? O20 Co1 N1 91.95(8) . . ? N2 Co1 N1 77.06(7) . . ? N2 Co1 N1 102.94(7) 3_575 . ? O20 Co1 N1 91.95(8) 3_575 3_575 ? O20 Co1 N1 88.05(8) . 3_575 ? N2 Co1 N1 102.94(7) . 3_575 ? N2 Co1 N1 77.06(7) 3_575 3_575 ? N1 Co1 N1 180.0 . 3_575 ? C1 N1 C5 118.1(2) . . ? C1 N1 Co1 125.46(16) . . ? C5 N1 Co1 116.21(14) . . ? C6 N2 N3 110.66(18) . . ? C6 N2 Co1 114.61(14) . . ? N3 N2 Co1 134.49(15) . . ? C7 N3 N2 105.64(19) . . ? C6 N4 C11 134.0(2) . . ? C6 N4 C7 104.84(19) . . ? C11 N4 C7 121.1(2) . . ? N1 C1 C2 122.7(2) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 118.9(2) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 118.7(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 122.0(2) . . ? N1 C5 C6 111.46(19) . . ? C4 C5 C6 126.5(2) . . ? N2 C6 N4 108.48(18) . . ? N2 C6 C5 120.23(19) . . ? N4 C6 C5 131.3(2) . . ? N3 C7 N4 110.36(19) . . ? N3 C7 C8 130.1(2) . . ? N4 C7 C8 119.6(2) . . ? C9 C8 C7 118.6(3) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C8 C9 C10 121.0(2) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C11 C10 C9 121.2(3) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 N4 118.5(2) . . ? C10 C11 H11 120.7 . . ? N4 C11 H11 120.7 . . ? C21 O20 Co1 126.59(18) . . ? C21 O20 H20 112(3) . . ? Co1 O20 H20 119(3) . . ? O20 C21 H21A 109.5 . . ? O20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 Cl1 O3 117.5(5) . . ? O4 Cl1 O7 143.9(4) . . ? O3 Cl1 O7 59.2(5) . . ? O4 Cl1 O1 103.0(3) . . ? O3 Cl1 O1 115.6(2) . . ? O7 Cl1 O1 110.3(3) . . ? O4 Cl1 O2 110.6(4) . . ? O3 Cl1 O2 108.1(4) . . ? O7 Cl1 O2 50.4(4) . . ? O1 Cl1 O2 100.7(3) . . ? O3 Cl1 O6 118.1(4) . . ? O7 Cl1 O6 104.3(5) . . ? O1 Cl1 O6 125.4(3) . . ? O2 Cl1 O6 71.1(4) . . ? O4 Cl1 O5 76.9(4) . . ? O3 Cl1 O5 47.5(4) . . ? O7 Cl1 O5 106.4(5) . . ? O1 Cl1 O5 105.2(3) . . ? O2 Cl1 O5 150.6(3) . . ? O6 Cl1 O5 103.8(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O20 Co1 N1 C1 87.75(19) 3_575 . . . ? O20 Co1 N1 C1 -92.25(19) . . . . ? N2 Co1 N1 C1 176.9(2) . . . . ? N2 Co1 N1 C1 -3.1(2) 3_575 . . . ? O20 Co1 N1 C5 -86.47(16) 3_575 . . . ? O20 Co1 N1 C5 93.53(16) . . . . ? N2 Co1 N1 C5 2.64(15) . . . . ? N2 Co1 N1 C5 -177.36(15) 3_575 . . . ? O20 Co1 N2 C6 89.95(16) 3_575 . . . ? O20 Co1 N2 C6 -90.05(16) . . . . ? N1 Co1 N2 C6 1.66(15) . . . . ? N1 Co1 N2 C6 -178.34(15) 3_575 . . . ? O20 Co1 N2 N3 -96.4(2) 3_575 . . . ? O20 Co1 N2 N3 83.6(2) . . . . ? N1 Co1 N2 N3 175.3(2) . . . . ? N1 Co1 N2 N3 -4.7(2) 3_575 . . . ? C6 N2 N3 C7 -0.2(2) . . . . ? Co1 N2 N3 C7 -174.00(16) . . . . ? C5 N1 C1 C2 0.2(4) . . . . ? Co1 N1 C1 C2 -173.97(19) . . . . ? N1 C1 C2 C3 1.6(4) . . . . ? C1 C2 C3 C4 -1.7(4) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C1 N1 C5 C4 -1.9(3) . . . . ? Co1 N1 C5 C4 172.81(17) . . . . ? C1 N1 C5 C6 179.42(19) . . . . ? Co1 N1 C5 C6 -5.9(2) . . . . ? C3 C4 C5 N1 1.7(4) . . . . ? C3 C4 C5 C6 -179.8(2) . . . . ? N3 N2 C6 N4 -0.3(2) . . . . ? Co1 N2 C6 N4 174.86(13) . . . . ? N3 N2 C6 C5 179.15(18) . . . . ? Co1 N2 C6 C5 -5.7(3) . . . . ? C11 N4 C6 N2 -177.0(2) . . . . ? C7 N4 C6 N2 0.6(2) . . . . ? C11 N4 C6 C5 3.6(4) . . . . ? C7 N4 C6 C5 -178.8(2) . . . . ? N1 C5 C6 N2 7.8(3) . . . . ? C4 C5 C6 N2 -170.9(2) . . . . ? N1 C5 C6 N4 -172.9(2) . . . . ? C4 C5 C6 N4 8.4(4) . . . . ? N2 N3 C7 N4 0.6(2) . . . . ? N2 N3 C7 C8 -179.5(2) . . . . ? C6 N4 C7 N3 -0.8(2) . . . . ? C11 N4 C7 N3 177.3(2) . . . . ? C6 N4 C7 C8 179.4(2) . . . . ? C11 N4 C7 C8 -2.6(3) . . . . ? N3 C7 C8 C9 -178.2(3) . . . . ? N4 C7 C8 C9 1.7(4) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? C8 C9 C10 C11 -1.1(4) . . . . ? C9 C10 C11 N4 0.2(4) . . . . ? C6 N4 C11 C10 179.0(2) . . . . ? C7 N4 C11 C10 1.7(3) . . . . ? N2 Co1 O20 C21 -24.0(2) . . . . ? N2 Co1 O20 C21 156.0(2) 3_575 . . . ? N1 Co1 O20 C21 -101.1(2) . . . . ? N1 Co1 O20 C21 78.9(2) 3_575 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.340 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.062 data_afp05 _database_code_depnum_ccdc_archive 'CCDC 755108' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C24 H24 N8 Ni O2, 2(Cl O4) ; _chemical_formula_sum 'C24 H24 Cl2 N8 Ni O10' _chemical_formula_weight 714.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(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 7.9685(16) _cell_length_b 12.135(2) _cell_length_c 15.114(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.35(3) _cell_angle_gamma 90.00 _cell_volume 1415.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 3226 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 27.90 _exptl_crystal_description needle _exptl_crystal_colour grey _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.675 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 0.946 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.6754 _exptl_absorpt_correction_T_max 0.9722 _exptl_absorpt_process_details ; March 2001 T Higashi ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 'Rigaku R-Axis SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22784 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.90 _reflns_number_total 3226 _reflns_number_gt 2293 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+1.1620P] 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 3226 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.0957 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 Ni1 Ni 0.0000 0.0000 0.0000 0.02885(14) Uani 1 2 d S . . N1 N -0.1336(3) -0.15125(19) -0.01040(14) 0.0324(5) Uani 1 1 d . . . N2 N 0.1924(3) -0.10166(19) 0.07446(14) 0.0315(5) Uani 1 1 d . . . N3 N 0.3662(3) -0.0901(2) 0.11732(16) 0.0376(5) Uani 1 1 d . . . N4 N 0.2873(3) -0.26643(19) 0.12111(14) 0.0321(5) Uani 1 1 d . . . C1 C -0.3032(3) -0.1685(3) -0.05227(19) 0.0399(7) Uani 1 1 d . . . H1 H -0.3680 -0.1100 -0.0846 0.048 Uiso 1 1 calc R . . C2 C -0.3844(4) -0.2694(3) -0.0491(2) 0.0451(7) Uani 1 1 d . . . H2 H -0.5014 -0.2796 -0.0796 0.054 Uiso 1 1 calc R . . C3 C -0.2892(4) -0.3536(3) -0.0003(2) 0.0476(8) Uani 1 1 d . . . H3 H -0.3420 -0.4221 0.0039 0.057 Uiso 1 1 calc R . . C4 C -0.1131(4) -0.3380(3) 0.0434(2) 0.0425(7) Uani 1 1 d . . . H4 H -0.0474 -0.3952 0.0771 0.051 Uiso 1 1 calc R . . C5 C -0.0393(3) -0.2373(2) 0.03588(17) 0.0312(6) Uani 1 1 d . . . C6 C 0.1440(3) -0.2053(2) 0.07686(16) 0.0296(6) Uani 1 1 d . . . C7 C 0.4227(3) -0.1903(2) 0.14610(18) 0.0350(6) Uani 1 1 d . . . C8 C 0.5924(4) -0.2263(3) 0.1948(2) 0.0451(7) Uani 1 1 d . . . H8 H 0.6837 -0.1757 0.2130 0.054 Uiso 1 1 calc R . . C9 C 0.6170(4) -0.3344(3) 0.2134(2) 0.0509(8) Uani 1 1 d . . . H9 H 0.7268 -0.3596 0.2455 0.061 Uiso 1 1 calc R . . C10 C 0.4788(4) -0.4110(3) 0.1853(2) 0.0500(8) Uani 1 1 d . . . H10 H 0.5001 -0.4862 0.1981 0.060 Uiso 1 1 calc R . . C11 C 0.3154(4) -0.3781(3) 0.1398(2) 0.0428(7) Uani 1 1 d . . . H11 H 0.2251 -0.4295 0.1219 0.051 Uiso 1 1 calc R . . O20 O -0.0724(3) 0.0347(2) 0.11815(15) 0.0450(5) Uani 1 1 d . . . H20 H -0.017(4) 0.007(3) 0.163(2) 0.055(11) Uiso 1 1 d . . . C21 C -0.2450(4) 0.0575(3) 0.1222(2) 0.0563(9) Uani 1 1 d . . . H21A H -0.2877 0.1212 0.0846 0.084 Uiso 1 1 calc R . . H21B H -0.2474 0.0726 0.1849 0.084 Uiso 1 1 calc R . . H21C H -0.3178 -0.0056 0.0999 0.084 Uiso 1 1 calc R . . Cl1 Cl 0.09243(9) -0.12671(6) 0.33008(5) 0.04169(19) Uani 1 1 d . . . O1 O 0.1992(3) -0.1308(3) 0.42051(16) 0.0853(10) Uani 1 1 d . A . O2 O -0.0771(5) -0.0867(6) 0.3352(4) 0.073(2) Uani 0.592(10) 1 d P A 1 O3 O 0.0514(9) -0.2241(5) 0.2731(4) 0.089(2) Uani 0.592(10) 1 d P A 1 O4 O 0.1578(8) -0.0507(7) 0.2794(4) 0.103(4) Uani 0.592(10) 1 d P A 1 O5 O 0.2258(11) -0.1470(10) 0.2857(5) 0.095(4) Uani 0.408(10) 1 d P A 2 O6 O 0.0133(18) -0.0263(7) 0.2988(5) 0.105(6) Uani 0.408(10) 1 d P A 2 O7 O -0.0091(11) -0.2161(8) 0.3253(7) 0.098(4) Uani 0.408(10) 1 d P A 2 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 0.0227(2) 0.0334(3) 0.0301(2) 0.0003(2) 0.00592(17) -0.0002(2) N1 0.0250(11) 0.0385(14) 0.0336(12) -0.0017(10) 0.0072(9) -0.0017(10) N2 0.0254(11) 0.0352(13) 0.0332(12) -0.0012(10) 0.0060(9) -0.0010(9) N3 0.0243(11) 0.0447(15) 0.0408(13) 0.0021(11) 0.0023(9) 0.0002(10) N4 0.0317(11) 0.0382(13) 0.0267(11) 0.0031(10) 0.0079(9) 0.0038(10) C1 0.0302(14) 0.0438(17) 0.0424(16) -0.0010(13) 0.0030(12) 0.0001(13) C2 0.0295(14) 0.0492(19) 0.0554(18) -0.0084(15) 0.0078(13) -0.0091(14) C3 0.0443(17) 0.0418(19) 0.060(2) -0.0075(15) 0.0188(15) -0.0130(14) C4 0.0392(16) 0.0401(17) 0.0503(17) 0.0020(14) 0.0149(13) -0.0031(13) C5 0.0309(13) 0.0344(15) 0.0305(13) -0.0030(11) 0.0117(11) -0.0015(11) C6 0.0271(12) 0.0368(15) 0.0249(12) 0.0007(11) 0.0068(10) 0.0030(11) C7 0.0283(13) 0.0454(17) 0.0304(14) -0.0003(12) 0.0057(11) 0.0014(12) C8 0.0328(15) 0.059(2) 0.0410(16) 0.0019(15) 0.0035(12) 0.0052(14) C9 0.0389(16) 0.068(2) 0.0438(17) 0.0082(16) 0.0068(13) 0.0149(16) C10 0.0501(18) 0.052(2) 0.0481(18) 0.0169(15) 0.0125(15) 0.0182(16) C11 0.0480(17) 0.0399(17) 0.0419(16) 0.0073(13) 0.0140(13) 0.0033(14) O20 0.0416(12) 0.0615(15) 0.0352(11) 0.0046(10) 0.0157(9) 0.0102(10) C21 0.0490(19) 0.071(2) 0.058(2) 0.0059(18) 0.0307(16) 0.0081(17) Cl1 0.0434(4) 0.0445(4) 0.0377(4) 0.0035(3) 0.0111(3) 0.0045(3) O1 0.0583(15) 0.146(3) 0.0465(14) 0.0329(16) 0.0030(12) 0.0141(17) O2 0.035(2) 0.105(5) 0.075(4) -0.017(3) 0.007(2) 0.019(2) O3 0.124(5) 0.069(4) 0.072(4) -0.021(3) 0.023(4) 0.017(3) O4 0.067(4) 0.156(9) 0.072(3) 0.067(4) -0.007(3) -0.045(5) O5 0.096(6) 0.151(10) 0.054(4) 0.001(5) 0.047(4) 0.028(6) O6 0.172(14) 0.062(6) 0.053(5) -0.011(4) -0.026(6) 0.066(8) O7 0.079(6) 0.109(8) 0.092(7) 0.013(6) -0.008(5) -0.066(5) _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 O20 2.052(2) . ? Ni1 O20 2.052(2) 3 ? Ni1 N2 2.070(2) 3 ? Ni1 N2 2.070(2) . ? Ni1 N1 2.108(2) 3 ? Ni1 N1 2.108(2) . ? N1 C1 1.359(3) . ? N1 C5 1.372(3) . ? N2 C6 1.319(3) . ? N2 N3 1.383(3) . ? N3 C7 1.332(4) . ? N4 C6 1.387(3) . ? N4 C11 1.391(4) . ? N4 C7 1.399(3) . ? C1 C2 1.391(4) . ? C1 H1 0.9400 . ? C2 C3 1.374(4) . ? C2 H2 0.9400 . ? C3 C4 1.408(4) . ? C3 H3 0.9400 . ? C4 C5 1.373(4) . ? C4 H4 0.9400 . ? C5 C6 1.490(4) . ? C7 C8 1.438(4) . ? C8 C9 1.346(5) . ? C8 H8 0.9400 . ? C9 C10 1.423(5) . ? C9 H9 0.9400 . ? C10 C11 1.373(4) . ? C10 H10 0.9400 . ? C11 H11 0.9400 . ? O20 C21 1.419(3) . ? O20 H20 0.78(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? Cl1 O7 1.344(7) . ? Cl1 O4 1.381(4) . ? Cl1 O6 1.399(6) . ? Cl1 O5 1.411(7) . ? Cl1 O1 1.420(2) . ? Cl1 O3 1.450(5) . ? Cl1 O2 1.455(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 O20 Ni1 O20 180.0 . 3 ? O20 Ni1 N2 91.19(9) . 3 ? O20 Ni1 N2 88.81(9) 3 3 ? O20 Ni1 N2 88.81(9) . . ? O20 Ni1 N2 91.19(9) 3 . ? N2 Ni1 N2 180.0 3 . ? O20 Ni1 N1 90.12(9) . 3 ? O20 Ni1 N1 89.88(9) 3 3 ? N2 Ni1 N1 79.28(8) 3 3 ? N2 Ni1 N1 100.72(8) . 3 ? O20 Ni1 N1 89.88(9) . . ? O20 Ni1 N1 90.12(9) 3 . ? N2 Ni1 N1 100.72(8) 3 . ? N2 Ni1 N1 79.28(8) . . ? N1 Ni1 N1 180.0 3 . ? C1 N1 C5 118.4(2) . . ? C1 N1 Ni1 126.46(19) . . ? C5 N1 Ni1 114.95(16) . . ? C6 N2 N3 110.5(2) . . ? C6 N2 Ni1 113.64(16) . . ? N3 N2 Ni1 135.63(18) . . ? C7 N3 N2 106.1(2) . . ? C6 N4 C11 133.7(2) . . ? C6 N4 C7 105.3(2) . . ? C11 N4 C7 120.9(2) . . ? N1 C1 C2 122.5(3) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 118.3(3) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 120.3(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 118.6(3) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 121.9(2) . . ? N1 C5 C6 111.8(2) . . ? C4 C5 C6 126.4(3) . . ? N2 C6 N4 108.1(2) . . ? N2 C6 C5 120.0(2) . . ? N4 C6 C5 131.8(2) . . ? N3 C7 N4 109.9(2) . . ? N3 C7 C8 130.1(3) . . ? N4 C7 C8 120.1(3) . . ? C9 C8 C7 118.3(3) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C8 C9 C10 120.8(3) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 121.8(3) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C10 C11 N4 118.0(3) . . ? C10 C11 H11 121.0 . . ? N4 C11 H11 121.0 . . ? C21 O20 Ni1 124.2(2) . . ? C21 O20 H20 113(3) . . ? Ni1 O20 H20 116(3) . . ? O20 C21 H21A 109.5 . . ? O20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O7 Cl1 O4 144.5(5) . . ? O7 Cl1 O6 118.0(7) . . ? O4 Cl1 O6 55.4(6) . . ? O7 Cl1 O5 110.4(6) . . ? O4 Cl1 O5 54.6(5) . . ? O6 Cl1 O5 108.7(7) . . ? O7 Cl1 O1 103.4(4) . . ? O4 Cl1 O1 109.8(2) . . ? O6 Cl1 O1 117.9(3) . . ? O5 Cl1 O1 96.3(4) . . ? O4 Cl1 O3 106.0(4) . . ? O6 Cl1 O3 119.5(4) . . ? O5 Cl1 O3 70.2(5) . . ? O1 Cl1 O3 122.4(3) . . ? O7 Cl1 O2 73.6(5) . . ? O4 Cl1 O2 106.8(4) . . ? O6 Cl1 O2 51.7(6) . . ? O5 Cl1 O2 154.3(4) . . ? O1 Cl1 O2 107.6(3) . . ? O3 Cl1 O2 103.1(3) . . ? 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 O20 Ni1 N1 C1 88.3(2) . . . . ? O20 Ni1 N1 C1 -91.7(2) 3 . . . ? N2 Ni1 N1 C1 -2.9(2) 3 . . . ? N2 Ni1 N1 C1 177.1(2) . . . . ? O20 Ni1 N1 C5 -86.83(18) . . . . ? O20 Ni1 N1 C5 93.17(18) 3 . . . ? N2 Ni1 N1 C5 -178.01(17) 3 . . . ? N2 Ni1 N1 C5 1.98(17) . . . . ? O20 Ni1 N2 C6 92.07(18) . . . . ? O20 Ni1 N2 C6 -87.93(18) 3 . . . ? N1 Ni1 N2 C6 -178.04(17) 3 . . . ? N1 Ni1 N2 C6 1.96(17) . . . . ? O20 Ni1 N2 N3 -94.2(2) . . . . ? O20 Ni1 N2 N3 85.8(2) 3 . . . ? N1 Ni1 N2 N3 -4.3(2) 3 . . . ? N1 Ni1 N2 N3 175.7(2) . . . . ? C6 N2 N3 C7 0.0(3) . . . . ? Ni1 N2 N3 C7 -173.89(19) . . . . ? C5 N1 C1 C2 0.6(4) . . . . ? Ni1 N1 C1 C2 -174.4(2) . . . . ? N1 C1 C2 C3 1.2(4) . . . . ? C1 C2 C3 C4 -1.3(5) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C1 N1 C5 C4 -2.3(4) . . . . ? Ni1 N1 C5 C4 173.3(2) . . . . ? C1 N1 C5 C6 179.4(2) . . . . ? Ni1 N1 C5 C6 -5.1(3) . . . . ? C3 C4 C5 N1 2.1(4) . . . . ? C3 C4 C5 C6 -179.8(3) . . . . ? N3 N2 C6 N4 -0.7(3) . . . . ? Ni1 N2 C6 N4 174.58(15) . . . . ? N3 N2 C6 C5 179.1(2) . . . . ? Ni1 N2 C6 C5 -5.6(3) . . . . ? C11 N4 C6 N2 -176.8(3) . . . . ? C7 N4 C6 N2 1.2(3) . . . . ? C11 N4 C6 C5 3.4(5) . . . . ? C7 N4 C6 C5 -178.6(2) . . . . ? N1 C5 C6 N2 7.2(3) . . . . ? C4 C5 C6 N2 -171.1(3) . . . . ? N1 C5 C6 N4 -173.0(2) . . . . ? C4 C5 C6 N4 8.7(4) . . . . ? N2 N3 C7 N4 0.8(3) . . . . ? N2 N3 C7 C8 -180.0(3) . . . . ? C6 N4 C7 N3 -1.2(3) . . . . ? C11 N4 C7 N3 177.1(2) . . . . ? C6 N4 C7 C8 179.5(2) . . . . ? C11 N4 C7 C8 -2.3(4) . . . . ? N3 C7 C8 C9 -177.9(3) . . . . ? N4 C7 C8 C9 1.3(4) . . . . ? C7 C8 C9 C10 0.4(4) . . . . ? C8 C9 C10 C11 -1.3(5) . . . . ? C9 C10 C11 N4 0.4(4) . . . . ? C6 N4 C11 C10 179.1(3) . . . . ? C7 N4 C11 C10 1.4(4) . . . . ? N2 Ni1 O20 C21 32.2(3) 3 . . . ? N2 Ni1 O20 C21 -147.8(3) . . . . ? N1 Ni1 O20 C21 111.5(3) 3 . . . ? N1 Ni1 O20 C21 -68.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.387 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.075 data_afp06 _database_code_depnum_ccdc_archive 'CCDC 755109' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C13 H8 Cu N6 S2 ; _chemical_formula_sum 'C13 H8 Cu N6 S2' _chemical_formula_weight 375.91 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 19.057(4) _cell_length_b 5.5459(11) _cell_length_c 13.697(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1447.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2915 _cell_measurement_theta_min 3.66 _cell_measurement_theta_max 27.47 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 1.800 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5714 _exptl_absorpt_correction_T_max 0.9480 _exptl_absorpt_process_details ; March 2001 T Higashi ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku R-Axis SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13886 _diffrn_reflns_av_R_equivalents 0.0937 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2915 _reflns_number_gt 2384 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+2.7959P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.016(19) _refine_ls_number_reflns 2915 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.68164(3) 0.06755(10) 0.45778(5) 0.01920(14) Uani 1 1 d . . . N1 N 0.7015(2) 0.3535(8) 0.5497(3) 0.0209(10) Uani 1 1 d . . . N2 N 0.7830(2) 0.1244(7) 0.4312(3) 0.0189(10) Uani 1 1 d . . . N3 N 0.8273(2) 0.0303(8) 0.3637(3) 0.0223(10) Uani 1 1 d . . . N4 N 0.8710(2) 0.3754(7) 0.4234(3) 0.0184(10) Uani 1 1 d . . . C1 C 0.6571(3) 0.4509(9) 0.6126(4) 0.0235(12) Uani 1 1 d . . . H1 H 0.6117 0.3817 0.6186 0.028 Uiso 1 1 calc R . . C2 C 0.6734(3) 0.6484(9) 0.6702(4) 0.0265(12) Uani 1 1 d . . . H2 H 0.6404 0.7098 0.7159 0.032 Uiso 1 1 calc R . . C3 C 0.7382(3) 0.7537(9) 0.6599(4) 0.0262(12) Uani 1 1 d . . . H3 H 0.7500 0.8924 0.6971 0.031 Uiso 1 1 calc R . . C4 C 0.7864(3) 0.6567(9) 0.5947(4) 0.0215(11) Uani 1 1 d . . . H4 H 0.8318 0.7252 0.5875 0.026 Uiso 1 1 calc R . . C5 C 0.7662(3) 0.4550(9) 0.5399(4) 0.0186(11) Uani 1 1 d . . . C6 C 0.8082(2) 0.3286(7) 0.4682(4) 0.0163(10) Uani 1 1 d . . . C7 C 0.8812(3) 0.1844(9) 0.3584(4) 0.0194(11) Uani 1 1 d . . . C8 C 0.9425(2) 0.1754(10) 0.3013(4) 0.0251(12) Uani 1 1 d . . . H8 H 0.9506 0.0442 0.2581 0.030 Uiso 1 1 calc R . . C9 C 0.9894(3) 0.3557(10) 0.3088(4) 0.0271(13) Uani 1 1 d . . . H9 H 1.0302 0.3539 0.2690 0.033 Uiso 1 1 calc R . . C10 C 0.9786(3) 0.5508(10) 0.3761(4) 0.0273(12) Uani 1 1 d . . . H10 H 1.0127 0.6751 0.3812 0.033 Uiso 1 1 calc R . . C11 C 0.9204(2) 0.5592(9) 0.4323(4) 0.0221(12) Uani 1 1 d . . . H11 H 0.9132 0.6880 0.4769 0.026 Uiso 1 1 calc R . . N20 N 0.5883(2) 0.0203(8) 0.5110(3) 0.0274(11) Uani 1 1 d . . . C20 C 0.5343(3) -0.0275(9) 0.5469(4) 0.0232(12) Uani 1 1 d . . . S20 S 0.46025(8) -0.0909(3) 0.60075(11) 0.0311(4) Uani 1 1 d . . . N21 N 0.6791(2) -0.2365(8) 0.3839(4) 0.0229(10) Uani 1 1 d . . . C21 C 0.6688(3) -0.4205(9) 0.3480(4) 0.0203(11) Uani 1 1 d . . . S21 S 0.65424(7) -0.6820(2) 0.29568(10) 0.0219(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0197(3) 0.0169(3) 0.0210(3) -0.0001(3) 0.0011(3) -0.0016(2) N1 0.022(2) 0.023(2) 0.018(2) -0.0017(18) -0.0018(19) 0.0015(18) N2 0.019(2) 0.020(2) 0.018(3) -0.0018(16) 0.0002(17) 0.0036(17) N3 0.017(2) 0.027(2) 0.023(2) -0.007(2) 0.0031(19) -0.0005(18) N4 0.018(2) 0.016(2) 0.021(2) -0.0007(16) -0.0028(18) 0.0020(17) C1 0.029(3) 0.024(3) 0.017(3) 0.000(2) 0.008(2) 0.004(2) C2 0.035(3) 0.026(3) 0.018(3) -0.003(2) 0.004(3) 0.008(2) C3 0.037(3) 0.017(3) 0.024(3) -0.005(2) -0.006(3) 0.002(2) C4 0.022(3) 0.028(3) 0.015(3) -0.002(2) -0.005(2) 0.003(2) C5 0.025(3) 0.016(3) 0.015(3) 0.000(2) -0.003(2) 0.002(2) C6 0.021(2) 0.013(2) 0.015(3) -0.001(2) -0.004(2) 0.0034(17) C7 0.021(3) 0.018(3) 0.019(3) 0.001(2) 0.000(2) 0.001(2) C8 0.019(3) 0.033(3) 0.023(3) -0.004(3) 0.000(3) -0.001(2) C9 0.023(3) 0.035(3) 0.023(3) -0.003(2) 0.003(3) 0.001(2) C10 0.022(3) 0.030(3) 0.030(3) -0.004(3) -0.004(2) -0.007(2) C11 0.020(2) 0.020(3) 0.026(4) -0.002(2) -0.003(2) -0.003(2) N20 0.028(3) 0.026(3) 0.029(3) 0.001(2) -0.002(2) -0.005(2) C20 0.028(3) 0.022(3) 0.020(3) 0.001(2) -0.004(2) -0.006(2) S20 0.0256(7) 0.0435(9) 0.0241(8) -0.0037(7) 0.0020(6) -0.0118(6) N21 0.022(2) 0.020(3) 0.027(3) 0.005(2) 0.000(2) -0.0032(19) C21 0.019(3) 0.016(3) 0.025(3) 0.002(2) 0.000(2) -0.003(2) S21 0.0249(6) 0.0175(6) 0.0234(7) -0.0010(6) -0.0019(6) -0.0007(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 Cu1 N20 1.940(5) . ? Cu1 N21 1.968(5) . ? Cu1 N2 1.991(4) . ? Cu1 N1 2.060(4) . ? Cu1 S21 2.6705(16) 1_565 ? N1 C1 1.323(7) . ? N1 C5 1.361(7) . ? N2 C6 1.330(6) . ? N2 N3 1.358(6) . ? N3 C7 1.337(6) . ? N4 C6 1.370(6) . ? N4 C11 1.392(6) . ? N4 C7 1.397(6) . ? C1 C2 1.385(7) . ? C1 H1 0.9500 . ? C2 C3 1.373(7) . ? C2 H2 0.9500 . ? C3 C4 1.390(7) . ? C3 H3 0.9500 . ? C4 C5 1.400(7) . ? C4 H4 0.9500 . ? C5 C6 1.448(7) . ? C7 C8 1.406(7) . ? C8 C9 1.345(7) . ? C8 H8 0.9500 . ? C9 C10 1.437(7) . ? C9 H9 0.9500 . ? C10 C11 1.351(7) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? N20 C20 1.171(7) . ? C20 S20 1.630(6) . ? N21 C21 1.149(6) . ? C21 S21 1.641(5) . ? S21 Cu1 2.6706(16) 1_545 ? 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 N20 Cu1 N21 93.16(19) . . ? N20 Cu1 N2 168.41(18) . . ? N21 Cu1 N2 93.78(17) . . ? N20 Cu1 N1 92.46(18) . . ? N21 Cu1 N1 168.20(18) . . ? N2 Cu1 N1 79.11(17) . . ? N20 Cu1 S21 101.75(14) . 1_565 ? N21 Cu1 S21 90.74(14) . 1_565 ? N2 Cu1 S21 87.44(12) . 1_565 ? N1 Cu1 S21 98.27(13) . 1_565 ? C1 N1 C5 118.3(5) . . ? C1 N1 Cu1 126.5(4) . . ? C5 N1 Cu1 115.1(3) . . ? C6 N2 N3 111.2(4) . . ? C6 N2 Cu1 114.5(3) . . ? N3 N2 Cu1 131.9(3) . . ? C7 N3 N2 105.6(4) . . ? C6 N4 C11 133.6(4) . . ? C6 N4 C7 105.3(4) . . ? C11 N4 C7 121.1(4) . . ? N1 C1 C2 123.4(5) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 118.6(5) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 119.7(5) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 118.1(5) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? N1 C5 C4 121.8(5) . . ? N1 C5 C6 111.5(4) . . ? C4 C5 C6 126.7(5) . . ? N2 C6 N4 107.8(4) . . ? N2 C6 C5 118.1(4) . . ? N4 C6 C5 134.0(4) . . ? N3 C7 N4 110.1(4) . . ? N3 C7 C8 130.1(5) . . ? N4 C7 C8 119.8(5) . . ? C9 C8 C7 118.9(5) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 120.9(5) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C11 C10 C9 120.6(5) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 N4 118.7(5) . . ? C10 C11 H11 120.7 . . ? N4 C11 H11 120.7 . . ? C20 N20 Cu1 173.8(4) . . ? N20 C20 S20 177.8(5) . . ? C21 N21 Cu1 170.1(4) . . ? N21 C21 S21 179.5(5) . . ? C21 S21 Cu1 93.7(2) . 1_545 ? 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 N20 Cu1 N1 C1 -3.7(5) . . . . ? N21 Cu1 N1 C1 -122.0(9) . . . . ? N2 Cu1 N1 C1 -175.7(5) . . . . ? S21 Cu1 N1 C1 98.6(4) 1_565 . . . ? N20 Cu1 N1 C5 179.4(4) . . . . ? N21 Cu1 N1 C5 61.1(11) . . . . ? N2 Cu1 N1 C5 7.4(4) . . . . ? S21 Cu1 N1 C5 -78.3(4) 1_565 . . . ? N20 Cu1 N2 C6 -55.2(11) . . . . ? N21 Cu1 N2 C6 178.2(4) . . . . ? N1 Cu1 N2 C6 -11.3(4) . . . . ? S21 Cu1 N2 C6 87.6(3) 1_565 . . . ? N20 Cu1 N2 N3 144.0(8) . . . . ? N21 Cu1 N2 N3 17.4(5) . . . . ? N1 Cu1 N2 N3 -172.1(5) . . . . ? S21 Cu1 N2 N3 -73.2(4) 1_565 . . . ? C6 N2 N3 C7 -0.8(5) . . . . ? Cu1 N2 N3 C7 160.5(4) . . . . ? C5 N1 C1 C2 -1.1(8) . . . . ? Cu1 N1 C1 C2 -177.9(4) . . . . ? N1 C1 C2 C3 1.9(9) . . . . ? C1 C2 C3 C4 -1.9(8) . . . . ? C2 C3 C4 C5 1.2(8) . . . . ? C1 N1 C5 C4 0.3(8) . . . . ? Cu1 N1 C5 C4 177.5(4) . . . . ? C1 N1 C5 C6 -179.7(4) . . . . ? Cu1 N1 C5 C6 -2.5(5) . . . . ? C3 C4 C5 N1 -0.4(7) . . . . ? C3 C4 C5 C6 179.6(5) . . . . ? N3 N2 C6 N4 0.8(6) . . . . ? Cu1 N2 C6 N4 -164.0(3) . . . . ? N3 N2 C6 C5 178.6(4) . . . . ? Cu1 N2 C6 C5 13.9(6) . . . . ? C11 N4 C6 N2 -179.7(5) . . . . ? C7 N4 C6 N2 -0.4(5) . . . . ? C11 N4 C6 C5 2.9(9) . . . . ? C7 N4 C6 C5 -177.8(5) . . . . ? N1 C5 C6 N2 -7.3(6) . . . . ? C4 C5 C6 N2 172.7(5) . . . . ? N1 C5 C6 N4 169.9(5) . . . . ? C4 C5 C6 N4 -10.1(9) . . . . ? N2 N3 C7 N4 0.5(5) . . . . ? N2 N3 C7 C8 179.1(5) . . . . ? C6 N4 C7 N3 0.0(6) . . . . ? C11 N4 C7 N3 179.4(4) . . . . ? C6 N4 C7 C8 -178.9(5) . . . . ? C11 N4 C7 C8 0.5(7) . . . . ? N3 C7 C8 C9 179.7(6) . . . . ? N4 C7 C8 C9 -1.7(8) . . . . ? C7 C8 C9 C10 2.0(8) . . . . ? C8 C9 C10 C11 -1.1(9) . . . . ? C9 C10 C11 N4 -0.2(8) . . . . ? C6 N4 C11 C10 179.6(5) . . . . ? C7 N4 C11 C10 0.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.793 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.113 data_afp07 _database_code_depnum_ccdc_archive 'CCDC 755110' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C22 H20 Co N8 O2, 2(Cl O4) ; _chemical_formula_sum 'C22 H20 Cl2 Co N8 O10' _chemical_formula_weight 686.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 7.7590(16) _cell_length_b 12.306(3) _cell_length_c 14.779(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.56(3) _cell_angle_gamma 90.00 _cell_volume 1365.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 2942 _cell_measurement_theta_min 3.18 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 698 _exptl_absorpt_coefficient_mu 0.895 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7506 _exptl_absorpt_correction_T_max 0.8774 _exptl_absorpt_process_details ; March 2001 T Higashi ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 'Rigaku R-Axis SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12943 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2942 _reflns_number_gt 2545 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.9917P] 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 2942 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.0000 1.0000 0.0000 0.02344(12) Uani 1 2 d S . . N1 N -0.1556(2) 1.14378(13) -0.00225(12) 0.0277(4) Uani 1 1 d . . . N2 N 0.1226(2) 1.11192(13) -0.06990(12) 0.0266(4) Uani 1 1 d . . . N3 N 0.2603(3) 1.10636(15) -0.11147(13) 0.0317(4) Uani 1 1 d . . . N4 N 0.1430(3) 1.27290(14) -0.12767(12) 0.0292(4) Uani 1 1 d . . . C1 C -0.2928(3) 1.15212(19) 0.03657(17) 0.0349(5) Uani 1 1 d . . . H1 H -0.3335 1.0894 0.0610 0.042 Uiso 1 1 calc R . . C2 C -0.3776(4) 1.2502(2) 0.04209(19) 0.0427(6) Uani 1 1 d . . . H2 H -0.4739 1.2538 0.0699 0.051 Uiso 1 1 calc R . . C3 C -0.3189(4) 1.3417(2) 0.0065(2) 0.0455(6) Uani 1 1 d . . . H3 H -0.3731 1.4091 0.0109 0.055 Uiso 1 1 calc R . . C4 C -0.1789(3) 1.33437(18) -0.03593(19) 0.0393(5) Uani 1 1 d . . . H4 H -0.1390 1.3963 -0.0619 0.047 Uiso 1 1 calc R . . C5 C -0.0988(3) 1.23419(16) -0.03945(14) 0.0271(4) Uani 1 1 d . . . C6 C 0.0515(3) 1.21038(15) -0.07887(14) 0.0260(4) Uani 1 1 d . . . C7 C 0.2719(3) 1.20470(18) -0.14718(15) 0.0315(5) Uani 1 1 d . . . C8 C 0.3904(4) 1.2443(2) -0.19783(17) 0.0414(6) Uani 1 1 d . . . H8 H 0.4780 1.1991 -0.2117 0.050 Uiso 1 1 calc R . . C9 C 0.3744(4) 1.3493(2) -0.2259(2) 0.0507(7) Uani 1 1 d . . . H9 H 0.4525 1.3775 -0.2594 0.061 Uiso 1 1 calc R . . O1 O 0.1737(3) 1.04989(15) 0.12560(13) 0.0449(5) Uani 1 1 d . . . H1A H 0.203(5) 1.110(3) 0.136(3) 0.070(11) Uiso 1 1 d . . . H1B H 0.210(5) 1.015(3) 0.172(3) 0.059(10) Uiso 1 1 d . . . C10 C 0.2426(4) 1.4168(2) -0.2058(2) 0.0521(7) Uani 1 1 d . . . H10 H 0.2343 1.4893 -0.2264 0.063 Uiso 1 1 calc R . . C11 C 0.1279(4) 1.38040(19) -0.15783(18) 0.0426(6) Uani 1 1 d . . . H11 H 0.0401 1.4263 -0.1451 0.051 Uiso 1 1 calc R . . Cl1 Cl 0.27432(7) 1.36860(4) 0.16609(4) 0.03207(15) Uani 1 1 d . . . O11 O 0.2401(3) 1.3882(2) 0.06887(14) 0.0665(6) Uani 1 1 d . A . O12 O 0.1711(7) 1.4412(4) 0.2080(3) 0.0447(15) Uani 0.64(2) 1 d P A 1 O13 O 0.4589(8) 1.3842(8) 0.2101(5) 0.064(2) Uani 0.64(2) 1 d P A 1 O14 O 0.2210(19) 1.2605(7) 0.1813(10) 0.090(3) Uani 0.64(2) 1 d P A 1 O22 O 0.144(3) 1.4122(19) 0.2046(15) 0.141(8) Uani 0.36(2) 1 d P A 2 O23 O 0.434(3) 1.4172(16) 0.2080(12) 0.100(6) Uani 0.36(2) 1 d P A 2 O24 O 0.297(2) 1.2562(12) 0.1864(15) 0.070(5) Uani 0.36(2) 1 d P A 2 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 0.0295(2) 0.01784(18) 0.0245(2) 0.00001(13) 0.00970(17) 0.00049(14) N1 0.0328(10) 0.0235(8) 0.0284(9) -0.0003(6) 0.0107(8) 0.0028(6) N2 0.0306(9) 0.0223(8) 0.0289(9) -0.0004(6) 0.0112(8) 0.0000(6) N3 0.0333(10) 0.0309(9) 0.0344(10) 0.0005(7) 0.0151(9) -0.0017(7) N4 0.0366(10) 0.0242(8) 0.0258(9) 0.0032(6) 0.0060(8) -0.0055(7) C1 0.0383(13) 0.0346(11) 0.0349(12) 0.0017(9) 0.0152(11) 0.0054(9) C2 0.0403(14) 0.0478(14) 0.0429(14) -0.0045(11) 0.0160(12) 0.0141(11) C3 0.0493(15) 0.0336(12) 0.0530(16) -0.0054(10) 0.0114(13) 0.0158(10) C4 0.0446(14) 0.0236(10) 0.0489(14) 0.0008(9) 0.0101(12) 0.0063(9) C5 0.0320(11) 0.0226(9) 0.0249(10) -0.0023(7) 0.0036(9) 0.0008(8) C6 0.0316(11) 0.0216(9) 0.0239(10) 0.0006(7) 0.0052(9) -0.0021(7) C7 0.0339(12) 0.0333(11) 0.0272(11) -0.0024(8) 0.0072(10) -0.0066(9) C8 0.0427(14) 0.0495(14) 0.0352(13) -0.0001(10) 0.0157(12) -0.0116(11) C9 0.0567(17) 0.0566(16) 0.0406(14) 0.0075(12) 0.0154(14) -0.0227(13) O1 0.0675(13) 0.0257(9) 0.0323(9) 0.0017(7) -0.0047(9) -0.0082(8) C10 0.070(2) 0.0383(13) 0.0483(16) 0.0161(11) 0.0153(15) -0.0143(13) C11 0.0564(16) 0.0278(11) 0.0421(14) 0.0106(9) 0.0097(12) -0.0031(10) Cl1 0.0380(3) 0.0226(2) 0.0355(3) -0.00545(18) 0.0090(2) 0.00095(19) O11 0.0795(16) 0.0820(16) 0.0310(10) -0.0044(10) 0.0011(11) 0.0069(12) O12 0.045(2) 0.039(2) 0.045(2) -0.0203(15) 0.001(2) 0.0107(15) O13 0.034(2) 0.108(5) 0.046(3) -0.006(3) 0.0014(19) 0.021(3) O14 0.140(8) 0.025(2) 0.132(8) -0.019(3) 0.083(7) -0.021(4) O22 0.146(12) 0.088(10) 0.25(2) 0.017(9) 0.166(14) 0.026(8) O23 0.091(10) 0.078(8) 0.101(8) 0.003(6) -0.032(8) -0.062(8) O24 0.076(8) 0.022(3) 0.096(9) 0.003(4) -0.008(7) -0.001(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N2 2.0888(17) 3_575 ? Co1 N2 2.0888(17) . ? Co1 O1 2.0931(19) . ? Co1 O1 2.0931(19) 3_575 ? Co1 N1 2.1376(17) 3_575 ? Co1 N1 2.1376(17) . ? N1 C1 1.334(3) . ? N1 C5 1.363(3) . ? N2 C6 1.324(3) . ? N2 N3 1.361(3) . ? N3 C7 1.332(3) . ? N4 C6 1.369(3) . ? N4 C7 1.390(3) . ? N4 C11 1.392(3) . ? C1 C2 1.387(3) . ? C1 H1 0.9400 . ? C2 C3 1.368(4) . ? C2 H2 0.9400 . ? C3 C4 1.387(4) . ? C3 H3 0.9400 . ? C4 C5 1.387(3) . ? C4 H4 0.9400 . ? C5 C6 1.459(3) . ? C7 C8 1.411(3) . ? C8 C9 1.352(4) . ? C8 H8 0.9400 . ? C9 C10 1.406(5) . ? C9 H9 0.9400 . ? O1 H1A 0.77(4) . ? O1 H1B 0.80(4) . ? C10 C11 1.346(4) . ? C10 H10 0.9400 . ? C11 H11 0.9400 . ? Cl1 O23 1.373(13) . ? Cl1 O22 1.389(13) . ? Cl1 O11 1.415(2) . ? Cl1 O24 1.417(15) . ? Cl1 O14 1.427(9) . ? Cl1 O13 1.429(7) . ? Cl1 O12 1.439(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Co1 N2 180.0 3_575 . ? N2 Co1 O1 91.52(8) 3_575 . ? N2 Co1 O1 88.48(8) . . ? N2 Co1 O1 88.48(8) 3_575 3_575 ? N2 Co1 O1 91.52(8) . 3_575 ? O1 Co1 O1 180.00(11) . 3_575 ? N2 Co1 N1 76.84(7) 3_575 3_575 ? N2 Co1 N1 103.16(7) . 3_575 ? O1 Co1 N1 89.64(8) . 3_575 ? O1 Co1 N1 90.36(8) 3_575 3_575 ? N2 Co1 N1 103.16(7) 3_575 . ? N2 Co1 N1 76.84(7) . . ? O1 Co1 N1 90.36(8) . . ? O1 Co1 N1 89.64(8) 3_575 . ? N1 Co1 N1 180.0 3_575 . ? C1 N1 C5 119.00(18) . . ? C1 N1 Co1 124.45(15) . . ? C5 N1 Co1 116.32(14) . . ? C6 N2 N3 110.80(17) . . ? C6 N2 Co1 115.02(14) . . ? N3 N2 Co1 134.16(13) . . ? C7 N3 N2 105.77(18) . . ? C6 N4 C7 105.38(17) . . ? C6 N4 C11 133.6(2) . . ? C7 N4 C11 121.0(2) . . ? N1 C1 C2 122.2(2) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 119.0(2) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 119.7(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 118.9(2) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? N1 C5 C4 121.1(2) . . ? N1 C5 C6 111.68(17) . . ? C4 C5 C6 127.2(2) . . ? N2 C6 N4 108.00(18) . . ? N2 C6 C5 119.91(18) . . ? N4 C6 C5 132.08(18) . . ? N3 C7 N4 110.05(19) . . ? N3 C7 C8 130.0(2) . . ? N4 C7 C8 120.0(2) . . ? C9 C8 C7 118.1(3) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C8 C9 C10 121.0(3) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? Co1 O1 H1A 123(3) . . ? Co1 O1 H1B 128(2) . . ? H1A O1 H1B 108(4) . . ? C11 C10 C9 121.8(2) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C10 C11 N4 118.1(3) . . ? C10 C11 H11 120.9 . . ? N4 C11 H11 120.9 . . ? O23 Cl1 O22 108.3(10) . . ? O23 Cl1 O11 107.5(8) . . ? O22 Cl1 O11 112.4(9) . . ? O23 Cl1 O24 106.2(9) . . ? O22 Cl1 O24 110.9(9) . . ? O11 Cl1 O24 111.3(9) . . ? O23 Cl1 O14 126.8(8) . . ? O22 Cl1 O14 91.4(9) . . ? O11 Cl1 O14 109.3(6) . . ? O22 Cl1 O13 120.8(11) . . ? O11 Cl1 O13 110.5(3) . . ? O24 Cl1 O13 88.7(6) . . ? O14 Cl1 O13 110.5(6) . . ? O23 Cl1 O12 94.1(10) . . ? O11 Cl1 O12 110.4(2) . . ? O24 Cl1 O12 124.6(9) . . ? O14 Cl1 O12 107.2(4) . . ? O13 Cl1 O12 108.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Co1 N1 C1 1.8(2) 3_575 . . . ? N2 Co1 N1 C1 -178.2(2) . . . . ? O1 Co1 N1 C1 -89.86(19) . . . . ? O1 Co1 N1 C1 90.14(19) 3_575 . . . ? N2 Co1 N1 C5 176.14(15) 3_575 . . . ? N2 Co1 N1 C5 -3.86(15) . . . . ? O1 Co1 N1 C5 84.50(16) . . . . ? O1 Co1 N1 C5 -95.50(16) 3_575 . . . ? O1 Co1 N2 C6 -89.41(16) . . . . ? O1 Co1 N2 C6 90.59(16) 3_575 . . . ? N1 Co1 N2 C6 -178.69(15) 3_575 . . . ? N1 Co1 N2 C6 1.31(15) . . . . ? NO1 Co1 N2 N3 92.4(2) . . . . ? O1 Co1 N2 N3 -87.6(2) 3_575 . . . ? N1 Co1 N2 N3 3.1(2) 3_575 . . . ? N1 Co1 N2 N3 -176.9(2) . . . . ? C6 N2 N3 C7 -0.4(2) . . . . ? Co1 N2 N3 C7 177.87(16) . . . . ? C5 N1 C1 C2 -1.3(4) . . . . ? Co1 N1 C1 C2 172.89(19) . . . . ? N1 C1 C2 C3 0.0(4) . . . . ? C1 C2 C3 C4 1.3(4) . . . . ? C2 C3 C4 C5 -1.4(4) . . . . ? C1 N1 C5 C4 1.2(3) . . . . ? Co1 N1 C5 C4 -173.45(17) . . . . ? C1 N1 C5 C6 -179.92(19) . . . . ? Co1 N1 C5 C6 5.4(2) . . . . ? C3 C4 C5 N1 0.1(4) . . . . ? C3 C4 C5 C6 -178.5(2) . . . . ? N3 N2 C6 N4 0.0(2) . . . . ? Co1 N2 C6 N4 -178.56(13) . . . . ? N3 N2 C6 C5 179.84(18) . . . . ? Co1 N2 C6 C5 1.2(2) . . . . ? C7 N4 C6 N2 0.3(2) . . . . ? C11 N4 C6 N2 179.6(2) . . . . ? C7 N4 C6 C5 -179.5(2) . . . . ? C11 N4 C6 C5 -0.2(4) . . . . ? N1 C5 C6 N2 -4.4(3) . . . . ? C4 C5 C6 N2 174.3(2) . . . . ? N1 C5 C6 N4 175.3(2) . . . . ? C4 C5 C6 N4 -5.9(4) . . . . ? N2 N3 C7 N4 0.5(2) . . . . ? N2 N3 C7 C8 -179.8(2) . . . . ? C6 N4 C7 N3 -0.5(2) . . . . ? C11 N4 C7 N3 -179.9(2) . . . . ? C6 N4 C7 C8 179.8(2) . . . . ? C11 N4 C7 C8 0.3(3) . . . . ? N3 C7 C8 C9 -179.5(2) . . . . ? N4 C7 C8 C9 0.1(4) . . . . ? C7 C8 C9 C10 -0.4(4) . . . . ? C8 C9 C10 C11 0.2(5) . . . . ? C9 C10 C11 N4 0.3(4) . . . . ? C6 N4 C11 C10 -179.8(2) . . . . ? C7 N4 C11 C10 -0.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.355 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.084 data_jmk09_2 _database_code_depnum_ccdc_archive 'CCDC 755111' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; 2(C33 H24 Fe N12), 1.75(C5 H12 O), 4(C F3 O3 S), 3(C2 H3 N), ; _chemical_formula_sum 'C84.75 H78.48 F12 Fe2 N27 O14 S4' _chemical_formula_weight 2167.17 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 13.508(3) _cell_length_b 13.547(3) _cell_length_c 15.078(3) _cell_angle_alpha 103.77(3) _cell_angle_beta 105.46(3) _cell_angle_gamma 99.56(3) _cell_volume 2504.3(9) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8515 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 24.74 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.469 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9121 _exptl_absorpt_correction_T_max 0.9724 _exptl_absorpt_process_details ; March 2001 T Higashi ; _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 'Rigaku R-Axis SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38719 _diffrn_reflns_av_R_equivalents 0.1085 _diffrn_reflns_av_sigmaI/netI 0.0875 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 24.74 _reflns_number_total 8515 _reflns_number_gt 4847 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1681P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8515 _refine_ls_number_parameters 703 _refine_ls_number_restraints 58 _refine_ls_R_factor_all 0.1477 _refine_ls_R_factor_gt 0.0889 _refine_ls_wR_factor_ref 0.2798 _refine_ls_wR_factor_gt 0.2356 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.071 _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 Fe1 Fe 0.75867(6) 0.75961(6) 0.52922(7) 0.0404(3) Uani 1 1 d . . . N101 N 0.8032(4) 0.8691(4) 0.6555(4) 0.0460(13) Uani 1 1 d . . . N102 N 0.6288(4) 0.8047(4) 0.5181(4) 0.0449(13) Uani 1 1 d . . . N103 N 0.5319(4) 0.7702(4) 0.4491(4) 0.0457(13) Uani 1 1 d . . . N104 N 0.5317(4) 0.9011(4) 0.5709(4) 0.0484(14) Uani 1 1 d . . . C101 C 0.8970(5) 0.8975(5) 0.7234(6) 0.0554(18) Uani 1 1 d . . . H101 H 0.9502 0.8626 0.7133 0.066 Uiso 1 1 calc R . . C102 C 0.9191(6) 0.9750(6) 0.8068(6) 0.067(2) Uani 1 1 d . . . H102 H 0.9863 0.9915 0.8548 0.080 Uiso 1 1 calc R . . C103 C 0.8443(7) 1.0308(7) 0.8230(7) 0.077(2) Uani 1 1 d . . . H103 H 0.8600 1.0864 0.8805 0.093 Uiso 1 1 calc R . . C104 C 0.7494(6) 1.0032(6) 0.7543(6) 0.067(2) Uani 1 1 d . . . H104 H 0.6963 1.0390 0.7631 0.080 Uiso 1 1 calc R . . C105 C 0.7289(5) 0.9223(5) 0.6702(5) 0.0472(16) Uani 1 1 d . . . C106 C 0.6310(5) 0.8812(5) 0.5916(5) 0.0436(15) Uani 1 1 d . . . C107 C 0.4712(5) 0.8290(5) 0.4817(5) 0.0434(15) Uani 1 1 d . . . C108 C 0.3645(5) 0.8254(5) 0.4416(6) 0.0556(18) Uani 1 1 d . . . H108 H 0.3230 0.7759 0.3814 0.067 Uiso 1 1 calc R . . C109 C 0.3213(6) 0.8945(5) 0.4905(6) 0.0573(19) Uani 1 1 d . . . H109 H 0.2486 0.8935 0.4650 0.069 Uiso 1 1 calc R . . C110 C 0.3854(5) 0.9686(5) 0.5805(6) 0.0561(19) Uani 1 1 d . . . H110 H 0.3549 1.0176 0.6136 0.067 Uiso 1 1 calc R . . C111 C 0.4871(5) 0.9708(5) 0.6193(5) 0.0509(17) Uani 1 1 d . . . H111 H 0.5282 1.0202 0.6798 0.061 Uiso 1 1 calc R . . N201 N 0.8063(4) 0.8569(4) 0.4606(4) 0.0438(13) Uani 1 1 d . . . N202 N 0.7071(4) 0.6669(4) 0.4001(4) 0.0417(12) Uani 1 1 d . . . N203 N 0.6515(4) 0.5647(4) 0.3614(4) 0.0436(13) Uani 1 1 d . . . N204 N 0.6848(4) 0.6301(4) 0.2462(4) 0.0472(13) Uani 1 1 d . . . C201 C 0.8587(5) 0.9586(5) 0.4999(6) 0.0501(17) Uani 1 1 d . . . H201 H 0.8766 0.9886 0.5675 0.060 Uiso 1 1 calc R . . C202 C 0.8875(5) 1.0212(6) 0.4469(7) 0.062(2) Uani 1 1 d . . . H202 H 0.9251 1.0924 0.4780 0.075 Uiso 1 1 calc R . . C203 C 0.8614(6) 0.9802(6) 0.3483(7) 0.068(2) Uani 1 1 d . . . H203 H 0.8787 1.0230 0.3104 0.082 Uiso 1 1 calc R . . C204 C 0.8093(5) 0.8746(5) 0.3058(6) 0.0557(18) Uani 1 1 d . . . H204 H 0.7921 0.8432 0.2384 0.067 Uiso 1 1 calc R . . C205 C 0.7829(5) 0.8163(5) 0.3641(6) 0.0488(17) Uani 1 1 d . . . C206 C 0.7264(5) 0.7062(5) 0.3326(5) 0.0417(15) Uani 1 1 d . . . C207 C 0.6378(5) 0.5429(5) 0.2677(5) 0.0475(16) Uani 1 1 d . . . C208 C 0.5853(5) 0.4488(5) 0.1931(6) 0.0559(18) Uani 1 1 d . . . H208 H 0.5519 0.3893 0.2067 0.067 Uiso 1 1 calc R . . C209 C 0.5831(7) 0.4441(6) 0.1021(6) 0.072(2) Uani 1 1 d . . . H209 H 0.5474 0.3816 0.0509 0.086 Uiso 1 1 calc R . . C210 C 0.6359(7) 0.5357(7) 0.0834(6) 0.074(2) Uani 1 1 d . . . H210 H 0.6359 0.5313 0.0195 0.089 Uiso 1 1 calc R . . C211 C 0.6844(6) 0.6257(6) 0.1527(6) 0.0612(19) Uani 1 1 d . . . H211 H 0.7178 0.6851 0.1390 0.073 Uiso 1 1 calc R . . N301 N 0.7156(4) 0.6452(4) 0.5828(4) 0.0404(12) Uani 1 1 d . . . N302 N 0.8876(4) 0.7121(4) 0.5546(4) 0.0425(12) Uani 1 1 d . . . N303 N 0.9846(4) 0.7462(4) 0.5455(4) 0.0460(13) Uani 1 1 d . . . N304 N 0.9815(4) 0.6053(4) 0.6002(4) 0.0389(12) Uani 1 1 d . . . C301 C 0.6201(5) 0.6136(5) 0.5926(5) 0.0446(15) Uani 1 1 d . . . H301 H 0.5689 0.6528 0.5786 0.054 Uiso 1 1 calc R . . C302 C 0.5934(5) 0.5269(5) 0.6220(5) 0.0468(16) Uani 1 1 d . . . H302 H 0.5254 0.5077 0.6284 0.056 Uiso 1 1 calc R . . C303 C 0.6652(5) 0.4688(5) 0.6417(5) 0.0504(17) Uani 1 1 d . . . H303 H 0.6476 0.4087 0.6618 0.060 Uiso 1 1 calc R . . C304 C 0.7645(5) 0.4989(5) 0.6321(5) 0.0468(16) Uani 1 1 d . . . H304 H 0.8157 0.4595 0.6453 0.056 Uiso 1 1 calc R . . C305 C 0.7874(4) 0.5872(4) 0.6031(5) 0.0386(14) Uani 1 1 d . . . C306 C 0.8857(4) 0.6303(4) 0.5875(5) 0.0386(14) Uani 1 1 d . . . C307 C 1.0401(4) 0.6805(5) 0.5721(5) 0.0419(15) Uani 1 1 d . . . C308 C 1.1462(5) 0.6777(5) 0.5770(5) 0.0462(16) Uani 1 1 d . . . H308 H 1.1886 0.7277 0.5589 0.055 Uiso 1 1 calc R . . C309 C 1.1849(5) 0.6019(5) 0.6079(5) 0.0516(18) Uani 1 1 d . . . H309 H 1.2556 0.5987 0.6120 0.062 Uiso 1 1 calc R . . C310 C 1.1220(5) 0.5274(5) 0.6343(5) 0.0492(16) Uani 1 1 d . . . H310 H 1.1518 0.4751 0.6557 0.059 Uiso 1 1 calc R . . C311 C 1.0211(5) 0.5274(5) 0.6303(5) 0.0445(15) Uani 1 1 d . . . H311 H 0.9794 0.4760 0.6474 0.053 Uiso 1 1 calc R . . S10 S 1.03480(13) 0.72308(13) 0.29322(15) 0.0559(5) Uani 1 1 d D . . O11 O 0.9292(4) 0.6684(4) 0.2734(5) 0.0829(18) Uani 1 1 d D . . O12 O 1.0541(5) 0.8347(4) 0.3103(5) 0.0863(19) Uani 1 1 d D . . O13 O 1.1107(4) 0.6913(4) 0.3606(4) 0.0736(16) Uani 1 1 d D . . C11 C 1.0611(10) 0.6761(9) 0.1854(8) 0.108(4) Uani 1 1 d D . . F11 F 1.1639(7) 0.7225(7) 0.1937(6) 0.166(3) Uani 1 1 d D . . F12 F 1.0095(9) 0.6958(8) 0.1126(6) 0.198(5) Uani 1 1 d D . . F13 F 1.0569(8) 0.5731(6) 0.1647(6) 0.179(4) Uani 1 1 d D . . S20 S 0.5360(4) 1.1784(3) 0.8737(3) 0.1430(15) Uani 1 1 d D . . O21 O 0.4418(13) 1.167(3) 0.8017(19) 0.50(3) Uani 0.757(14) 1 d PD A 1 O22 O 0.5568(15) 1.2098(9) 0.9795(8) 0.143(6) Uani 0.757(14) 1 d PD A 1 O23 O 0.5804(14) 1.0927(11) 0.8544(8) 0.197(8) Uani 0.757(14) 1 d PD A 1 O24 O 0.6191(9) 1.1596(9) 0.9150(10) 0.012(5) Uani 0.243(14) 1 d PDU A 2 O25 O 0.4300(13) 1.1466(16) 0.7939(12) 0.061(7) Uani 0.243(14) 1 d PDU A 2 O26 O 0.495(3) 1.223(3) 0.953(2) 0.19(4) Uani 0.243(14) 1 d PD A 2 C21 C 0.5911(8) 1.2879(11) 0.8464(8) 0.136(6) Uani 1 1 d D A . F21 F 0.6869(8) 1.3457(6) 0.9121(6) 0.159(3) Uani 1 1 d D . . F22 F 0.5462(7) 1.3610(7) 0.8524(7) 0.168(3) Uani 1 1 d D . . F23 F 0.6116(6) 1.2508(7) 0.7630(5) 0.158(3) Uani 1 1 d D . . N400 N 0.4563(8) 0.7546(7) 0.6876(9) 0.112(3) Uani 1 1 d D . . C400 C 0.4270(9) 0.8028(8) 0.7397(9) 0.090(3) Uani 1 1 d D . . C401 C 0.3841(14) 0.8673(12) 0.8089(12) 0.180(7) Uani 1 1 d D . . H40A H 0.3079 0.8376 0.7921 0.271 Uiso 1 1 calc R . . H40B H 0.3962 0.9395 0.8055 0.271 Uiso 1 1 calc R . . H40C H 0.4201 0.8671 0.8745 0.271 Uiso 1 1 calc R . . N500 N 1.1002(14) 0.7924(18) 0.8062(12) 0.142(10) Uani 0.50 1 d PD . . C500 C 1.1226(16) 0.739(2) 0.8474(13) 0.152(14) Uani 0.50 1 d PD . . C501 C 1.1529(19) 0.661(3) 0.8985(17) 0.198(18) Uani 0.50 1 d PD . . H50A H 1.1680 0.6098 0.8590 0.297 Uiso 0.50 1 d P . . H50B H 1.1001 0.6436 0.9253 0.297 Uiso 0.50 1 d P . . H50C H 1.2192 0.7033 0.9542 0.297 Uiso 0.50 1 d P . . C600 C 0.7797(12) 0.7581(16) -0.0591(11) 0.131(6) Uani 0.875(12) 1 d P B 1 C601 C 0.7154(13) 0.7655(13) -0.1519(10) 0.163(8) Uani 0.875(12) 1 d P B 1 H60A H 0.6444 0.7195 -0.1713 0.244 Uiso 0.875(12) 1 calc PR B 1 H60B H 0.7490 0.7438 -0.2010 0.244 Uiso 0.875(12) 1 calc PR B 1 H60C H 0.7102 0.8380 -0.1451 0.244 Uiso 0.875(12) 1 calc PR B 1 C602 C 0.8804(17) 0.8176(18) -0.0315(18) 0.226(13) Uani 0.875(12) 1 d P B 1 H60D H 0.9206 0.8128 0.0311 0.339 Uiso 0.875(12) 1 calc PR B 1 H60E H 0.8789 0.8908 -0.0264 0.339 Uiso 0.875(12) 1 calc PR B 1 H60F H 0.9142 0.7921 -0.0795 0.339 Uiso 0.875(12) 1 calc PR B 1 C603 C 0.7780(15) 0.6346(16) -0.0728(16) 0.196(10) Uani 0.875(12) 1 d P B 1 H60G H 0.7044 0.5931 -0.0960 0.294 Uiso 0.875(12) 1 calc PR B 1 H60H H 0.8149 0.6258 -0.0108 0.294 Uiso 0.875(12) 1 calc PR B 1 H60I H 0.8136 0.6107 -0.1197 0.294 Uiso 0.875(12) 1 calc PR B 1 O600 O 0.7277(13) 0.7595(14) 0.0065(11) 0.205(7) Uani 0.875(12) 1 d P B 1 C604 C 0.708(2) 0.8708(18) 0.0246(16) 0.259(15) Uani 0.875(12) 1 d P B 1 H60J H 0.6688 0.8809 0.0710 0.388 Uiso 0.875(12) 1 calc PR B 1 H60K H 0.6662 0.8787 -0.0363 0.388 Uiso 0.875(12) 1 calc PR B 1 H60L H 0.7758 0.9231 0.0504 0.388 Uiso 0.875(12) 1 calc PR B 1 O700 O 0.837(2) 0.9134(18) -0.0128(16) 0.068(13) Uani 0.125(12) 1 d PRU B 2 H70A H 0.8750 0.8945 -0.0274 0.102 Uiso 0.12 1 d P B 2 H70B H 0.8655 0.9961 0.0334 0.102 Uiso 0.12 1 d P B 2 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 0.0292(5) 0.0361(5) 0.0598(7) 0.0159(4) 0.0170(4) 0.0112(4) N101 0.038(3) 0.036(3) 0.062(4) 0.013(3) 0.014(3) 0.012(2) N102 0.033(3) 0.041(3) 0.061(4) 0.018(3) 0.013(3) 0.011(2) N103 0.030(3) 0.055(3) 0.058(4) 0.020(3) 0.013(3) 0.019(2) N104 0.042(3) 0.042(3) 0.068(4) 0.019(3) 0.021(3) 0.016(2) C101 0.044(4) 0.043(4) 0.068(5) 0.009(4) 0.006(4) 0.009(3) C102 0.049(4) 0.065(5) 0.076(6) 0.020(5) 0.004(4) 0.018(4) C103 0.062(5) 0.067(5) 0.088(7) 0.015(5) 0.007(5) 0.018(4) C104 0.061(5) 0.054(4) 0.077(6) 0.011(4) 0.014(4) 0.018(4) C105 0.049(4) 0.038(3) 0.057(4) 0.013(3) 0.021(4) 0.011(3) C106 0.039(4) 0.038(3) 0.059(4) 0.016(3) 0.020(3) 0.016(3) C107 0.032(3) 0.039(3) 0.055(4) 0.007(3) 0.014(3) 0.008(3) C108 0.045(4) 0.054(4) 0.074(5) 0.024(4) 0.019(4) 0.022(3) C109 0.047(4) 0.055(4) 0.081(6) 0.023(4) 0.027(4) 0.027(3) C110 0.052(4) 0.047(4) 0.079(5) 0.016(4) 0.032(4) 0.022(3) C111 0.050(4) 0.045(4) 0.064(5) 0.012(3) 0.028(4) 0.017(3) N201 0.024(3) 0.040(3) 0.063(4) 0.010(3) 0.009(3) 0.014(2) N202 0.030(3) 0.039(3) 0.060(4) 0.012(3) 0.019(3) 0.011(2) N203 0.035(3) 0.039(3) 0.057(4) 0.010(3) 0.017(3) 0.010(2) N204 0.044(3) 0.047(3) 0.061(4) 0.017(3) 0.028(3) 0.018(2) C201 0.032(3) 0.039(4) 0.080(5) 0.020(4) 0.017(3) 0.010(3) C202 0.038(4) 0.048(4) 0.107(7) 0.031(5) 0.027(4) 0.010(3) C203 0.055(5) 0.069(5) 0.105(8) 0.052(5) 0.037(5) 0.023(4) C204 0.051(4) 0.055(4) 0.077(5) 0.032(4) 0.032(4) 0.016(3) C205 0.034(3) 0.048(4) 0.076(5) 0.030(4) 0.022(4) 0.015(3) C206 0.036(3) 0.044(4) 0.057(4) 0.024(3) 0.024(3) 0.014(3) C207 0.039(4) 0.048(4) 0.062(5) 0.018(3) 0.020(3) 0.017(3) C208 0.049(4) 0.051(4) 0.062(5) 0.008(4) 0.015(4) 0.014(3) C209 0.074(6) 0.062(5) 0.069(6) 0.001(4) 0.016(5) 0.025(4) C210 0.077(6) 0.089(6) 0.061(5) 0.014(5) 0.029(5) 0.031(5) C211 0.065(5) 0.070(5) 0.060(5) 0.025(4) 0.027(4) 0.023(4) N301 0.027(3) 0.046(3) 0.050(3) 0.013(3) 0.014(2) 0.013(2) N302 0.035(3) 0.038(3) 0.055(3) 0.014(3) 0.017(3) 0.004(2) N303 0.026(3) 0.044(3) 0.070(4) 0.019(3) 0.018(3) 0.008(2) N304 0.029(3) 0.036(3) 0.053(3) 0.010(2) 0.016(2) 0.010(2) C301 0.028(3) 0.051(4) 0.055(4) 0.014(3) 0.015(3) 0.009(3) C302 0.038(4) 0.050(4) 0.052(4) 0.016(3) 0.016(3) 0.008(3) C303 0.048(4) 0.050(4) 0.063(5) 0.026(4) 0.027(4) 0.010(3) C304 0.040(4) 0.042(3) 0.069(5) 0.024(3) 0.025(3) 0.015(3) C305 0.029(3) 0.041(3) 0.047(4) 0.013(3) 0.014(3) 0.009(2) C306 0.030(3) 0.036(3) 0.053(4) 0.020(3) 0.011(3) 0.011(2) C307 0.026(3) 0.041(3) 0.060(4) 0.015(3) 0.015(3) 0.010(3) C308 0.026(3) 0.042(3) 0.070(5) 0.015(3) 0.018(3) 0.006(3) C309 0.032(3) 0.049(4) 0.078(5) 0.016(4) 0.023(4) 0.013(3) C310 0.037(4) 0.045(4) 0.067(5) 0.019(3) 0.015(3) 0.014(3) C311 0.035(3) 0.042(3) 0.061(4) 0.020(3) 0.015(3) 0.016(3) S10 0.0412(10) 0.0455(10) 0.0816(14) 0.0200(9) 0.0171(9) 0.0149(7) O11 0.044(3) 0.073(4) 0.125(5) 0.035(4) 0.016(3) 0.007(3) O12 0.084(4) 0.041(3) 0.140(6) 0.035(3) 0.037(4) 0.019(3) O13 0.046(3) 0.076(4) 0.101(4) 0.038(3) 0.014(3) 0.019(3) C11 0.141(11) 0.102(9) 0.083(8) 0.015(7) 0.046(8) 0.031(8) F11 0.181(8) 0.192(8) 0.200(9) 0.087(7) 0.142(8) 0.072(6) F12 0.268(12) 0.224(10) 0.073(5) 0.056(6) 0.005(6) 0.045(8) F13 0.292(12) 0.110(6) 0.150(7) 0.000(5) 0.109(8) 0.080(7) S20 0.159(4) 0.108(3) 0.146(3) -0.019(2) 0.077(3) 0.028(2) O21 0.091(13) 0.77(8) 0.41(4) -0.07(4) -0.079(19) 0.15(3) O22 0.253(18) 0.094(9) 0.091(8) -0.005(7) 0.107(10) 0.031(9) O23 0.40(2) 0.187(13) 0.080(8) 0.049(9) 0.096(12) 0.228(15) O24 0.011(5) 0.012(5) 0.012(5) 0.0035(17) 0.0035(18) 0.0041(15) O25 0.057(11) 0.060(10) 0.044(10) -0.013(7) 0.016(8) -0.003(7) O26 0.32(8) 0.12(3) 0.26(7) 0.09(4) 0.22(7) 0.15(5) C21 0.095(9) 0.288(19) 0.112(10) 0.130(12) 0.063(8) 0.129(12) F21 0.176(8) 0.159(7) 0.143(7) 0.039(6) 0.057(6) 0.043(6) F22 0.156(7) 0.189(8) 0.184(9) 0.051(7) 0.065(7) 0.093(7) F23 0.162(7) 0.242(9) 0.077(4) 0.020(5) 0.061(5) 0.073(6) N400 0.097(7) 0.084(6) 0.180(11) 0.060(7) 0.057(7) 0.034(5) C400 0.097(8) 0.071(7) 0.123(10) 0.058(7) 0.042(7) 0.024(5) C401 0.226(19) 0.164(14) 0.169(16) 0.056(13) 0.107(15) 0.012(13) N500 0.102(14) 0.27(3) 0.042(10) -0.002(12) -0.005(9) 0.146(17) C500 0.085(14) 0.34(4) 0.026(10) -0.003(16) -0.009(10) 0.15(2) C501 0.085(17) 0.44(6) 0.056(15) 0.05(2) 0.007(13) 0.11(3) C600 0.092(10) 0.203(19) 0.080(10) 0.028(10) 0.025(8) 0.019(11) C601 0.157(15) 0.172(15) 0.087(11) 0.046(10) -0.026(10) -0.055(12) C602 0.17(2) 0.21(2) 0.24(3) 0.12(2) -0.018(18) -0.044(17) C603 0.169(19) 0.179(19) 0.23(2) 0.107(18) 0.043(16) -0.023(15) O600 0.257(17) 0.228(16) 0.158(12) 0.094(12) 0.096(12) 0.029(14) C604 0.35(4) 0.22(3) 0.23(3) 0.02(2) 0.18(3) 0.06(3) O700 0.068(13) 0.068(13) 0.068(13) 0.020(4) 0.022(4) 0.017(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 Fe1 N202 1.917(5) . ? Fe1 N302 1.930(5) . ? Fe1 N102 1.931(5) . ? Fe1 N101 1.983(6) . ? Fe1 N301 1.985(5) . ? Fe1 N201 1.986(5) . ? N101 C101 1.326(9) . ? N101 C105 1.364(8) . ? N102 C106 1.315(8) . ? N102 N103 1.362(7) . ? N103 C107 1.339(7) . ? N104 C111 1.372(8) . ? N104 C106 1.381(8) . ? N104 C107 1.398(8) . ? C101 C102 1.357(10) . ? C101 H101 0.9500 . ? C102 C103 1.396(11) . ? C102 H102 0.9500 . ? C103 C104 1.343(11) . ? C103 H103 0.9500 . ? C104 C105 1.391(10) . ? C104 H104 0.9500 . ? C105 C106 1.439(9) . ? C107 C108 1.394(9) . ? C108 C109 1.357(9) . ? C108 H108 0.9500 . ? C109 C110 1.427(10) . ? C109 H109 0.9500 . ? C110 C111 1.334(10) . ? C110 H110 0.9500 . ? C111 H111 0.9500 . ? N201 C201 1.348(8) . ? N201 C205 1.354(9) . ? N202 C206 1.320(8) . ? N202 N203 1.363(7) . ? N203 C207 1.326(9) . ? N204 C206 1.362(8) . ? N204 C211 1.394(9) . ? N204 C207 1.396(8) . ? C201 C202 1.374(10) . ? C201 H201 0.9500 . ? C202 C203 1.380(11) . ? C202 H202 0.9500 . ? C203 C204 1.394(11) . ? C203 H203 0.9500 . ? C204 C205 1.388(9) . ? C204 H204 0.9500 . ? C205 C206 1.458(9) . ? C207 C208 1.409(10) . ? C208 C209 1.351(11) . ? C208 H208 0.9500 . ? C209 C210 1.452(11) . ? C209 H209 0.9500 . ? C210 C211 1.331(11) . ? C210 H210 0.9500 . ? C211 H211 0.9500 . ? N301 C301 1.349(7) . ? N301 C305 1.365(7) . ? N302 C306 1.317(7) . ? N302 N303 1.369(6) . ? N303 C307 1.323(7) . ? N304 C306 1.368(7) . ? N304 C311 1.375(7) . ? N304 C307 1.400(7) . ? C301 C302 1.377(9) . ? C301 H301 0.9500 . ? C302 C303 1.363(9) . ? C302 H302 0.9500 . ? C303 C304 1.391(8) . ? C303 H303 0.9500 . ? C304 C305 1.384(8) . ? C304 H304 0.9500 . ? C305 C306 1.461(8) . ? C307 C308 1.423(8) . ? C308 C309 1.349(9) . ? C308 H308 0.9500 . ? C309 C310 1.409(9) . ? C309 H309 0.9500 . ? C310 C311 1.347(8) . ? C310 H310 0.9500 . ? C311 H311 0.9500 . ? S10 O11 1.410(5) . ? S10 O13 1.437(5) . ? S10 O12 1.438(5) . ? S10 C11 1.751(10) . ? C11 F12 1.247(12) . ? C11 F13 1.344(11) . ? C11 F11 1.385(12) . ? S20 O24 1.229(10) . ? S20 O21 1.392(14) . ? S20 O23 1.398(9) . ? S20 O22 1.484(10) . ? S20 O26 1.488(15) . ? S20 O25 1.520(14) . ? S20 C21 1.735(12) . ? C21 F22 1.242(11) . ? C21 F23 1.358(11) . ? C21 F21 1.371(12) . ? N400 C400 1.098(12) . ? C400 C401 1.500(16) . ? C401 H40A 0.9800 . ? C401 H40B 0.9800 . ? C401 H40C 0.9800 . ? N500 C500 1.09(2) . ? C500 C501 1.50(2) . ? C501 H50A 0.8916 . ? C501 H50B 0.9325 . ? C501 H50C 1.0177 . ? C600 O600 1.356(18) . ? C600 C602 1.36(2) . ? C600 C601 1.473(19) . ? C600 C603 1.63(2) . ? C601 H60A 0.9800 . ? C601 H60B 0.9800 . ? C601 H60C 0.9800 . ? C602 H60D 0.9800 . ? C602 H60E 0.9800 . ? C602 H60F 0.9800 . ? C602 H70A 1.0446 . ? C603 H60G 0.9800 . ? C603 H60H 0.9800 . ? C603 H60I 0.9800 . ? O600 C604 1.55(2) . ? C604 H60J 0.9800 . ? C604 H60K 0.9800 . ? C604 H60L 0.9800 . ? O700 H70A 0.6701 . ? O700 H70B 1.1098 . ? 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 N202 Fe1 N302 91.1(2) . . ? N202 Fe1 N102 93.5(2) . . ? N302 Fe1 N102 173.2(2) . . ? N202 Fe1 N101 172.4(2) . . ? N302 Fe1 N101 95.0(2) . . ? N102 Fe1 N101 81.0(2) . . ? N202 Fe1 N301 92.2(2) . . ? N302 Fe1 N301 80.56(19) . . ? N102 Fe1 N301 94.24(19) . . ? N101 Fe1 N301 93.4(2) . . ? N202 Fe1 N201 80.3(2) . . ? N302 Fe1 N201 94.45(19) . . ? N102 Fe1 N201 91.3(2) . . ? N101 Fe1 N201 94.5(2) . . ? N301 Fe1 N201 171.0(2) . . ? C101 N101 C105 118.0(6) . . ? C101 N101 Fe1 127.2(5) . . ? C105 N101 Fe1 114.7(5) . . ? C106 N102 N103 112.1(5) . . ? C106 N102 Fe1 115.5(4) . . ? N103 N102 Fe1 132.3(4) . . ? C107 N103 N102 105.7(5) . . ? C111 N104 C106 133.6(6) . . ? C111 N104 C107 120.3(6) . . ? C106 N104 C107 106.1(5) . . ? N101 C101 C102 122.0(6) . . ? N101 C101 H101 119.0 . . ? C102 C101 H101 119.0 . . ? C101 C102 C103 120.7(8) . . ? C101 C102 H102 119.6 . . ? C103 C102 H102 119.6 . . ? C104 C103 C102 117.7(9) . . ? C104 C103 H103 121.1 . . ? C102 C103 H103 121.1 . . ? C103 C104 C105 120.0(8) . . ? C103 C104 H104 120.0 . . ? C105 C104 H104 120.0 . . ? N101 C105 C104 121.5(7) . . ? N101 C105 C106 111.6(6) . . ? C104 C105 C106 126.8(6) . . ? N102 C106 N104 106.9(6) . . ? N102 C106 C105 117.1(5) . . ? N104 C106 C105 136.0(6) . . ? N103 C107 C108 130.3(6) . . ? N103 C107 N104 109.1(5) . . ? C108 C107 N104 120.6(5) . . ? C109 C108 C107 118.5(7) . . ? C109 C108 H108 120.8 . . ? C107 C108 H108 120.8 . . ? C108 C109 C110 119.7(7) . . ? C108 C109 H109 120.2 . . ? C110 C109 H109 120.2 . . ? C111 C110 C109 121.7(6) . . ? C111 C110 H110 119.1 . . ? C109 C110 H110 119.1 . . ? C110 C111 N104 119.2(7) . . ? C110 C111 H111 120.4 . . ? N104 C111 H111 120.4 . . ? C201 N201 C205 117.0(6) . . ? C201 N201 Fe1 126.8(5) . . ? C205 N201 Fe1 116.2(4) . . ? C206 N202 N203 110.7(5) . . ? C206 N202 Fe1 116.7(4) . . ? N203 N202 Fe1 132.6(4) . . ? C207 N203 N202 105.3(5) . . ? C206 N204 C211 133.9(6) . . ? C206 N204 C207 104.4(5) . . ? C211 N204 C207 121.7(6) . . ? N201 C201 C202 123.2(8) . . ? N201 C201 H201 118.4 . . ? C202 C201 H201 118.4 . . ? C201 C202 C203 119.7(7) . . ? C201 C202 H202 120.2 . . ? C203 C202 H202 120.2 . . ? C202 C203 C204 118.5(7) . . ? C202 C203 H203 120.8 . . ? C204 C203 H203 120.8 . . ? C205 C204 C203 118.5(8) . . ? C205 C204 H204 120.8 . . ? C203 C204 H204 120.8 . . ? N201 C205 C204 123.2(6) . . ? N201 C205 C206 110.4(5) . . ? C204 C205 C206 126.4(7) . . ? N202 C206 N204 108.8(5) . . ? N202 C206 C205 116.3(6) . . ? N204 C206 C205 134.8(6) . . ? N203 C207 N204 110.8(6) . . ? N203 C207 C208 129.7(6) . . ? N204 C207 C208 119.5(6) . . ? C209 C208 C207 119.3(7) . . ? C209 C208 H208 120.4 . . ? C207 C208 H208 120.4 . . ? C208 C209 C210 119.4(8) . . ? C208 C209 H209 120.3 . . ? C210 C209 H209 120.3 . . ? C211 C210 C209 122.1(8) . . ? C211 C210 H210 118.9 . . ? C209 C210 H210 118.9 . . ? C210 C211 N204 118.0(7) . . ? C210 C211 H211 121.0 . . ? N204 C211 H211 121.0 . . ? C301 N301 C305 117.2(5) . . ? C301 N301 Fe1 126.6(4) . . ? C305 N301 Fe1 115.8(4) . . ? C306 N302 N303 110.6(5) . . ? C306 N302 Fe1 116.3(4) . . ? N303 N302 Fe1 133.1(4) . . ? C307 N303 N302 105.0(5) . . ? C306 N304 C311 133.5(5) . . ? C306 N304 C307 103.6(4) . . ? C311 N304 C307 122.9(5) . . ? N301 C301 C302 122.9(6) . . ? N301 C301 H301 118.5 . . ? C302 C301 H301 118.5 . . ? C303 C302 C301 119.6(6) . . ? C303 C302 H302 120.2 . . ? C301 C302 H302 120.2 . . ? C302 C303 C304 119.1(6) . . ? C302 C303 H303 120.5 . . ? C304 C303 H303 120.5 . . ? C305 C304 C303 118.9(6) . . ? C305 C304 H304 120.6 . . ? C303 C304 H304 120.6 . . ? N301 C305 C304 122.3(5) . . ? N301 C305 C306 110.5(5) . . ? C304 C305 C306 127.2(5) . . ? N302 C306 N304 109.3(5) . . ? N302 C306 C305 116.6(5) . . ? N304 C306 C305 134.1(5) . . ? N303 C307 N304 111.5(5) . . ? N303 C307 C308 129.9(5) . . ? N304 C307 C308 118.6(5) . . ? C309 C308 C307 118.0(6) . . ? C309 C308 H308 121.0 . . ? C307 C308 H308 121.0 . . ? C308 C309 C310 121.0(5) . . ? C308 C309 H309 119.5 . . ? C310 C309 H309 119.5 . . ? C311 C310 C309 122.5(6) . . ? C311 C310 H310 118.7 . . ? C309 C310 H310 118.7 . . ? C310 C311 N304 116.9(5) . . ? C310 C311 H311 121.6 . . ? N304 C311 H311 121.6 . . ? O11 S10 O13 113.5(3) . . ? O11 S10 O12 116.6(3) . . ? O13 S10 O12 114.0(4) . . ? O11 S10 C11 103.6(5) . . ? O13 S10 C11 102.5(5) . . ? O12 S10 C11 104.6(5) . . ? F12 C11 F13 109.9(10) . . ? F12 C11 F11 101.4(10) . . ? F13 C11 F11 104.4(10) . . ? F12 C11 S10 117.7(9) . . ? F13 C11 S10 111.6(8) . . ? F11 C11 S10 110.5(8) . . ? O24 S20 O21 158.8(15) . . ? O24 S20 O23 47.0(8) . . ? O21 S20 O23 112.1(15) . . ? O24 S20 O22 69.3(9) . . ? O21 S20 O22 127.8(14) . . ? O23 S20 O22 105.0(8) . . ? O24 S20 O26 104.5(15) . . ? O21 S20 O26 93(2) . . ? O23 S20 O26 132.7(15) . . ? O24 S20 O25 151.2(10) . . ? O23 S20 O25 104.2(11) . . ? O22 S20 O25 128.4(11) . . ? O26 S20 O25 95.5(16) . . ? O24 S20 C21 97.8(6) . . ? O21 S20 C21 88.9(14) . . ? O23 S20 C21 115.6(8) . . ? O22 S20 C21 106.8(7) . . ? O26 S20 C21 103.6(16) . . ? O25 S20 C21 97.4(9) . . ? F22 C21 F23 117.6(9) . . ? F22 C21 F21 96.0(12) . . ? F23 C21 F21 105.4(8) . . ? F22 C21 S20 117.3(8) . . ? F23 C21 S20 105.9(10) . . ? F21 C21 S20 114.2(7) . . ? N400 C400 C401 178.5(16) . . ? C400 C401 H40A 109.5 . . ? C400 C401 H40B 109.5 . . ? H40A C401 H40B 109.5 . . ? C400 C401 H40C 109.5 . . ? H40A C401 H40C 109.5 . . ? H40B C401 H40C 109.5 . . ? N500 C500 C501 176(2) . . ? C500 C501 H50A 109.5 . . ? C500 C501 H50B 107.1 . . ? H50A C501 H50B 118.5 . . ? C500 C501 H50C 103.6 . . ? H50A C501 H50C 110.2 . . ? H50B C501 H50C 106.9 . . ? O600 C600 C602 119.7(19) . . ? O600 C600 C601 113.9(15) . . ? C602 C600 C601 111.3(17) . . ? O600 C600 C603 91.4(16) . . ? C602 C600 C603 111.2(18) . . ? C601 C600 C603 107.1(15) . . ? C600 C601 H60A 109.5 . . ? C600 C601 H60B 109.5 . . ? H60A C601 H60B 109.5 . . ? C600 C601 H60C 109.5 . . ? H60A C601 H60C 109.5 . . ? H60B C601 H60C 109.5 . . ? C600 C602 H60D 109.5 . . ? C600 C602 H60E 109.5 . . ? H60D C602 H60E 109.5 . . ? C600 C602 H60F 109.5 . . ? H60D C602 H60F 109.5 . . ? H60E C602 H60F 109.5 . . ? C600 C602 H70A 106.8 . . ? H60D C602 H70A 111.1 . . ? H60F C602 H70A 110.5 . . ? C600 C603 H60G 109.5 . . ? C600 C603 H60H 109.5 . . ? H60G C603 H60H 109.5 . . ? C600 C603 H60I 109.5 . . ? H60G C603 H60I 109.5 . . ? H60H C603 H60I 109.5 . . ? C600 O600 C604 101.8(15) . . ? O600 C604 H60J 109.5 . . ? O600 C604 H60K 109.5 . . ? H60J C604 H60K 109.5 . . ? O600 C604 H60L 109.5 . . ? H60J C604 H60L 109.5 . . ? H60K C604 H60L 109.5 . . ? H70A O700 H70B 113.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N302 Fe1 N101 C101 5.4(6) . . . . ? N102 Fe1 N101 C101 179.9(6) . . . . ? N301 Fe1 N101 C101 86.2(6) . . . . ? N201 Fe1 N101 C101 -89.5(6) . . . . ? N302 Fe1 N101 C105 -177.4(4) . . . . ? N102 Fe1 N101 C105 -2.8(4) . . . . ? N301 Fe1 N101 C105 -96.6(4) . . . . ? N201 Fe1 N101 C105 87.7(4) . . . . ? N202 Fe1 N102 C106 -173.5(4) . . . . ? N101 Fe1 N102 C106 1.2(4) . . . . ? N301 Fe1 N102 C106 94.0(4) . . . . ? N201 Fe1 N102 C106 -93.1(5) . . . . ? N202 Fe1 N102 N103 9.0(5) . . . . ? N101 Fe1 N102 N103 -176.3(6) . . . . ? N301 Fe1 N102 N103 -83.5(5) . . . . ? N201 Fe1 N102 N103 89.3(5) . . . . ? C106 N102 N103 C107 0.2(7) . . . . ? Fe1 N102 N103 C107 177.8(4) . . . . ? C105 N101 C101 C102 1.8(10) . . . . ? Fe1 N101 C101 C102 179.0(5) . . . . ? N101 C101 C102 C103 -2.3(12) . . . . ? C101 C102 C103 C104 1.6(13) . . . . ? C102 C103 C104 C105 -0.6(13) . . . . ? C101 N101 C105 C104 -0.8(10) . . . . ? Fe1 N101 C105 C104 -178.3(5) . . . . ? C101 N101 C105 C106 -178.8(6) . . . . ? Fe1 N101 C105 C106 3.7(7) . . . . ? C103 C104 C105 N101 0.2(11) . . . . ? C103 C104 C105 C106 177.9(7) . . . . ? N103 N102 C106 N104 -1.2(7) . . . . ? Fe1 N102 C106 N104 -179.2(4) . . . . ? N103 N102 C106 C105 178.5(5) . . . . ? Fe1 N102 C106 C105 0.5(7) . . . . ? C111 N104 C106 N102 -180.0(6) . . . . ? C107 N104 C106 N102 1.6(6) . . . . ? C111 N104 C106 C105 0.5(12) . . . . ? C107 N104 C106 C105 -178.0(7) . . . . ? N101 C105 C106 N102 -2.8(8) . . . . ? C104 C105 C106 N102 179.4(6) . . . . ? N101 C105 C106 N104 176.8(6) . . . . ? C104 C105 C106 N104 -1.1(12) . . . . ? N102 N103 C107 C108 -178.0(7) . . . . ? N102 N103 C107 N104 0.8(7) . . . . ? C111 N104 C107 N103 179.8(5) . . . . ? C106 N104 C107 N103 -1.5(7) . . . . ? C111 N104 C107 C108 -1.2(9) . . . . ? C106 N104 C107 C108 177.5(6) . . . . ? N103 C107 C108 C109 179.6(6) . . . . ? N104 C107 C108 C109 0.8(10) . . . . ? C107 C108 C109 C110 0.4(10) . . . . ? C108 C109 C110 C111 -1.3(11) . . . . ? C109 C110 C111 N104 0.9(10) . . . . ? C106 N104 C111 C110 -178.0(6) . . . . ? C107 N104 C111 C110 0.3(9) . . . . ? N202 Fe1 N201 C201 179.3(5) . . . . ? N302 Fe1 N201 C201 -90.3(5) . . . . ? N102 Fe1 N201 C201 86.0(5) . . . . ? N101 Fe1 N201 C201 5.0(5) . . . . ? N202 Fe1 N201 C205 -0.2(4) . . . . ? N302 Fe1 N201 C205 90.1(4) . . . . ? N102 Fe1 N201 C205 -93.5(4) . . . . ? N101 Fe1 N201 C205 -174.5(4) . . . . ? N302 Fe1 N202 C206 -93.6(4) . . . . ? N102 Fe1 N202 C206 91.4(4) . . . . ? N301 Fe1 N202 C206 -174.2(4) . . . . ? N201 Fe1 N202 C206 0.7(4) . . . . ? N302 Fe1 N202 N203 87.2(5) . . . . ? N102 Fe1 N202 N203 -87.8(5) . . . . ? N301 Fe1 N202 N203 6.6(5) . . . . ? N201 Fe1 N202 N203 -178.5(5) . . . . ? C206 N202 N203 C207 0.3(6) . . . . ? Fe1 N202 N203 C207 179.5(4) . . . . ? C205 N201 C201 C202 0.6(8) . . . . ? Fe1 N201 C201 C202 -178.9(5) . . . . ? N201 C201 C202 C203 0.8(10) . . . . ? C201 C202 C203 C204 -2.1(10) . . . . ? C202 C203 C204 C205 2.0(10) . . . . ? C201 N201 C205 C204 -0.6(8) . . . . ? Fe1 N201 C205 C204 178.9(5) . . . . ? C201 N201 C205 C206 -179.9(5) . . . . ? Fe1 N201 C205 C206 -0.3(6) . . . . ? C203 C204 C205 N201 -0.7(9) . . . . ? C203 C204 C205 C206 178.4(6) . . . . ? N203 N202 C206 N204 -0.8(6) . . . . ? Fe1 N202 C206 N204 179.8(4) . . . . ? N203 N202 C206 C205 178.3(5) . . . . ? Fe1 N202 C206 C205 -1.1(6) . . . . ? C211 N204 C206 N202 -177.3(6) . . . . ? C207 N204 C206 N202 1.0(6) . . . . ? C211 N204 C206 C205 3.9(12) . . . . ? C207 N204 C206 C205 -177.8(6) . . . . ? N201 C205 C206 N202 0.9(7) . . . . ? C204 C205 C206 N202 -178.3(6) . . . . ? N201 C205 C206 N204 179.7(6) . . . . ? C204 C205 C206 N204 0.5(11) . . . . ? N202 N203 C207 N204 0.4(6) . . . . ? N202 N203 C207 C208 -179.7(6) . . . . ? C206 N204 C207 N203 -0.9(6) . . . . ? C211 N204 C207 N203 177.7(5) . . . . ? C206 N204 C207 C208 179.3(5) . . . . ? C211 N204 C207 C208 -2.2(9) . . . . ? N203 C207 C208 C209 -178.7(7) . . . . ? N204 C207 C208 C209 1.2(9) . . . . ? C207 C208 C209 C210 0.7(11) . . . . ? C208 C209 C210 C211 -1.8(12) . . . . ? C209 C210 C211 N204 0.8(11) . . . . ? C206 N204 C211 C210 179.2(7) . . . . ? C207 N204 C211 C210 1.1(10) . . . . ? N202 Fe1 N301 C301 -87.4(5) . . . . ? N302 Fe1 N301 C301 -178.1(6) . . . . ? N102 Fe1 N301 C301 6.3(6) . . . . ? N101 Fe1 N301 C301 87.4(5) . . . . ? N202 Fe1 N301 C305 86.1(5) . . . . ? N302 Fe1 N301 C305 -4.6(4) . . . . ? N102 Fe1 N301 C305 179.8(4) . . . . ? N101 Fe1 N301 C305 -99.1(5) . . . . ? N202 Fe1 N302 C306 -88.9(5) . . . . ? N101 Fe1 N302 C306 95.8(5) . . . . ? N301 Fe1 N302 C306 3.2(5) . . . . ? N201 Fe1 N302 C306 -169.2(5) . . . . ? N202 Fe1 N302 N303 91.2(6) . . . . ? N101 Fe1 N302 N303 -84.2(6) . . . . ? N301 Fe1 N302 N303 -176.7(6) . . . . ? N201 Fe1 N302 N303 10.8(6) . . . . ? C306 N302 N303 C307 1.4(7) . . . . ? Fe1 N302 N303 C307 -178.7(5) . . . . ? C305 N301 C301 C302 0.2(9) . . . . ? Fe1 N301 C301 C302 173.6(5) . . . . ? N301 C301 C302 C303 -0.5(10) . . . . ? C301 C302 C303 C304 0.3(10) . . . . ? C302 C303 C304 C305 0.2(10) . . . . ? C301 N301 C305 C304 0.4(9) . . . . ? Fe1 N301 C305 C304 -173.8(5) . . . . ? C301 N301 C305 C306 179.0(6) . . . . ? Fe1 N301 C305 C306 4.9(7) . . . . ? C303 C304 C305 N301 -0.6(10) . . . . ? C303 C304 C305 C306 -179.0(6) . . . . ? N303 N302 C306 N304 -1.1(7) . . . . ? Fe1 N302 C306 N304 179.0(4) . . . . ? N303 N302 C306 C305 178.5(5) . . . . ? Fe1 N302 C306 C305 -1.5(8) . . . . ? C311 N304 C306 N302 -178.4(6) . . . . ? C307 N304 C306 N302 0.3(7) . . . . ? C311 N304 C306 C305 2.2(12) . . . . ? C307 N304 C306 C305 -179.1(7) . . . . ? N301 C305 C306 N302 -2.3(8) . . . . ? C304 C305 C306 N302 176.3(6) . . . . ? N301 C305 C306 N304 177.2(7) . . . . ? C304 C305 C306 N304 -4.3(12) . . . . ? N302 N303 C307 N304 -1.1(7) . . . . ? N302 N303 C307 C308 179.9(7) . . . . ? C306 N304 C307 N303 0.5(7) . . . . ? C311 N304 C307 N303 179.4(6) . . . . ? C306 N304 C307 C308 179.6(6) . . . . ? C311 N304 C307 C308 -1.5(9) . . . . ? N303 C307 C308 C309 179.4(7) . . . . ? N304 C307 C308 C309 0.4(10) . . . . ? C307 C308 C309 C310 0.3(10) . . . . ? C308 C309 C310 C311 0.0(11) . . . . ? C309 C310 C311 N304 -1.0(10) . . . . ? C306 N304 C311 C310 -179.8(7) . . . . ? C307 N304 C311 C310 1.7(9) . . . . ? O11 S10 C11 F12 64.7(11) . . . . ? O13 S10 C11 F12 -177.1(10) . . . . ? O12 S10 C11 F12 -57.9(11) . . . . ? O11 S10 C11 F13 -63.8(10) . . . . ? O13 S10 C11 F13 54.5(10) . . . . ? O12 S10 C11 F13 173.7(9) . . . . ? O11 S10 C11 F11 -179.5(7) . . . . ? O13 S10 C11 F11 -61.3(8) . . . . ? O12 S10 C11 F11 57.9(9) . . . . ? O24 S20 C21 F22 -142.0(11) . . . . ? O21 S20 C21 F22 58.1(16) . . . . ? O23 S20 C21 F22 172.2(11) . . . . ? O22 S20 C21 F22 -71.4(13) . . . . ? O26 S20 C21 F22 -35.0(19) . . . . ? O25 S20 C21 F22 62.5(13) . . . . ? O24 S20 C21 F23 84.5(9) . . . . ? O21 S20 C21 F23 -75.4(15) . . . . ? O23 S20 C21 F23 38.7(10) . . . . ? O22 S20 C21 F23 155.1(10) . . . . ? O26 S20 C21 F23 -168.5(17) . . . . ? O25 S20 C21 F23 -71.0(10) . . . . ? O24 S20 C21 F21 -31.0(11) . . . . ? O21 S20 C21 F21 169.2(15) . . . . ? O23 S20 C21 F21 -76.7(11) . . . . ? O22 S20 C21 F21 39.7(12) . . . . ? O26 S20 C21 F21 76.0(18) . . . . ? O25 S20 C21 F21 173.6(11) . . . . ? C602 C600 O600 C604 70(2) . . . . ? C601 C600 O600 C604 -65(2) . . . . ? C603 C600 O600 C604 -174.2(16) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.74 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.185 _refine_diff_density_min -0.926 _refine_diff_density_rms 0.096 data_jmk107_1_10 _database_code_depnum_ccdc_archive 'CCDC 755112' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C24 H16 Fe N10 S2 ; _chemical_formula_sum 'C24 H16 Fe N10 S2' _chemical_formula_weight 564.44 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' S S 0.1246 0.1234 '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 8.8208(18) _cell_length_b 17.300(4) _cell_length_c 8.2926(17) _cell_angle_alpha 90.00 _cell_angle_beta 104.29(3) _cell_angle_gamma 90.00 _cell_volume 1226.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 288(2) _cell_measurement_reflns_used 1864 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 23.80 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.821 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8730 _exptl_absorpt_correction_T_max 0.9758 _exptl_absorpt_process_details ; March 2001 T Higashi ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 288(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 'Rigaku R-Axis SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14125 _diffrn_reflns_av_R_equivalents 0.0907 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 23.80 _reflns_number_total 1864 _reflns_number_gt 1309 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0298P)^2^+0.8700P] 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 1864 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0728 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0920 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 Fe1 Fe 1.0000 0.0000 0.0000 0.0365(2) Uani 1 2 d S . . N1 N 0.9710(4) -0.07823(16) 0.1887(4) 0.0436(8) Uani 1 1 d . . . C1 C 0.8715(5) -0.1381(2) 0.1668(5) 0.0544(11) Uani 1 1 d . . . H1 H 0.7962 -0.1424 0.0666 0.065 Uiso 1 1 calc R . . N2 N 1.1579(3) 0.04093(16) 0.2105(4) 0.0442(8) Uani 1 1 d . . . C2 C 0.8768(6) -0.1940(2) 0.2884(6) 0.0663(13) Uani 1 1 d . . . H2 H 0.8066 -0.2350 0.2695 0.080 Uiso 1 1 calc R . . N3 N 1.2550(4) 0.10333(17) 0.2450(4) 0.0475(8) Uani 1 1 d . . . C3 C 0.9855(6) -0.1878(3) 0.4344(7) 0.0777(15) Uani 1 1 d . . . H3 H 0.9908 -0.2251 0.5164 0.093 Uiso 1 1 calc R . . N4 N 1.2842(3) 0.03035(15) 0.4726(4) 0.0396(7) Uani 1 1 d . . . C4 C 1.0895(5) -0.1260(2) 0.4627(5) 0.0649(12) Uani 1 1 d . . . H4 H 1.1653 -0.1213 0.5625 0.078 Uiso 1 1 calc R . . C5 C 1.0766(4) -0.07147(19) 0.3376(5) 0.0419(9) Uani 1 1 d . . . C6 C 1.1739(4) -0.0027(2) 0.3445(4) 0.0408(8) Uani 1 1 d . . . C7 C 1.3323(4) 0.0966(2) 0.4036(5) 0.0423(9) Uani 1 1 d . . . C8 C 1.4489(5) 0.1440(2) 0.5021(5) 0.0511(10) Uani 1 1 d . . . H8 H 1.4829 0.1882 0.4576 0.061 Uiso 1 1 calc R . . C9 C 1.5101(5) 0.1243(2) 0.6618(5) 0.0545(11) Uani 1 1 d . . . H9 H 1.5866 0.1553 0.7284 0.065 Uiso 1 1 calc R . . C10 C 1.4593(5) 0.0564(2) 0.7301(5) 0.0554(11) Uani 1 1 d . . . H10 H 1.5031 0.0438 0.8408 0.066 Uiso 1 1 calc R . . C11 C 1.3489(4) 0.0104(2) 0.6370(5) 0.0493(10) Uani 1 1 d . . . H11 H 1.3165 -0.0341 0.6821 0.059 Uiso 1 1 calc R . . S20 S 0.63014(18) 0.17901(8) 0.12671(16) 0.0880(5) Uani 1 1 d . . . N20 N 0.8366(4) 0.07361(18) 0.0459(4) 0.0509(9) Uani 1 1 d . . . C20 C 0.7525(5) 0.1192(2) 0.0781(4) 0.0457(10) 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 0.0373(4) 0.0351(4) 0.0355(4) 0.0002(3) 0.0059(3) -0.0007(4) N1 0.0408(19) 0.0335(17) 0.057(2) -0.0075(15) 0.0140(17) -0.0061(15) C1 0.049(3) 0.046(2) 0.069(3) -0.013(2) 0.016(2) -0.010(2) N2 0.0429(19) 0.0355(17) 0.053(2) 0.0069(15) 0.0088(16) -0.0043(15) C2 0.079(4) 0.044(3) 0.085(4) -0.009(2) 0.038(3) -0.023(2) N3 0.052(2) 0.0369(18) 0.051(2) 0.0061(15) 0.0080(17) -0.0067(16) C3 0.104(4) 0.058(3) 0.075(4) 0.012(3) 0.029(3) -0.023(3) N4 0.0385(18) 0.0346(16) 0.0451(19) 0.0039(14) 0.0092(16) -0.0014(14) C4 0.079(3) 0.058(3) 0.056(3) 0.014(2) 0.014(2) -0.016(3) C5 0.041(2) 0.034(2) 0.054(3) 0.0002(18) 0.019(2) -0.0032(18) C6 0.040(2) 0.0348(19) 0.047(2) 0.0002(19) 0.0096(18) 0.0041(19) C7 0.044(2) 0.034(2) 0.047(2) -0.0023(18) 0.009(2) 0.0001(18) C8 0.056(3) 0.040(2) 0.056(3) 0.002(2) 0.011(2) -0.009(2) C9 0.053(3) 0.051(3) 0.056(3) -0.005(2) 0.007(2) -0.007(2) C10 0.059(3) 0.060(3) 0.044(2) 0.005(2) 0.006(2) 0.000(2) C11 0.052(2) 0.052(2) 0.041(2) 0.009(2) 0.0066(19) -0.001(2) S20 0.1194(12) 0.0813(9) 0.0694(9) 0.0121(7) 0.0351(8) 0.0550(9) N20 0.053(2) 0.052(2) 0.046(2) 0.0012(17) 0.0099(17) -0.0009(18) C20 0.055(3) 0.045(2) 0.037(2) 0.0036(18) 0.011(2) 0.001(2) _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 N20 2.028(3) 3_755 ? Fe1 N20 2.028(3) . ? Fe1 N2 2.071(3) . ? Fe1 N2 2.071(3) 3_755 ? Fe1 N1 2.132(3) 3_755 ? Fe1 N1 2.132(3) . ? N1 C1 1.341(4) . ? N1 C5 1.356(5) . ? C1 C2 1.389(6) . ? C1 H1 0.9300 . ? N2 C6 1.322(4) . ? N2 N3 1.364(4) . ? C2 C3 1.350(6) . ? C2 H2 0.9300 . ? N3 C7 1.329(4) . ? C3 C4 1.392(6) . ? C3 H3 0.9300 . ? N4 C6 1.375(4) . ? N4 C11 1.386(4) . ? N4 C7 1.393(4) . ? C4 C5 1.386(5) . ? C4 H4 0.9300 . ? C5 C6 1.460(5) . ? C7 C8 1.408(5) . ? C8 C9 1.345(5) . ? C8 H8 0.9300 . ? C9 C10 1.423(5) . ? C9 H9 0.9300 . ? C10 C11 1.345(5) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? S20 C20 1.616(4) . ? N20 C20 1.159(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 N20 Fe1 N20 180.0 3_755 . ? N20 Fe1 N2 90.65(12) 3_755 . ? N20 Fe1 N2 89.35(12) . . ? N20 Fe1 N2 89.35(12) 3_755 3_755 ? N20 Fe1 N2 90.65(12) . 3_755 ? N2 Fe1 N2 180.0 . 3_755 ? N20 Fe1 N1 92.36(11) 3_755 3_755 ? N20 Fe1 N1 87.64(11) . 3_755 ? N2 Fe1 N1 102.93(12) . 3_755 ? N2 Fe1 N1 77.07(12) 3_755 3_755 ? N20 Fe1 N1 87.64(11) 3_755 . ? N20 Fe1 N1 92.36(11) . . ? N2 Fe1 N1 77.07(12) . . ? N2 Fe1 N1 102.93(12) 3_755 . ? N1 Fe1 N1 180.0 3_755 . ? C1 N1 C5 118.0(3) . . ? C1 N1 Fe1 125.8(3) . . ? C5 N1 Fe1 115.7(2) . . ? N1 C1 C2 122.4(4) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C6 N2 N3 110.1(3) . . ? C6 N2 Fe1 115.0(2) . . ? N3 N2 Fe1 134.8(2) . . ? C3 C2 C1 119.1(4) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C7 N3 N2 106.3(3) . . ? C2 C3 C4 120.3(4) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C6 N4 C11 134.2(3) . . ? C6 N4 C7 104.7(3) . . ? C11 N4 C7 121.1(3) . . ? C5 C4 C3 117.9(4) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? N1 C5 C4 122.3(3) . . ? N1 C5 C6 111.8(3) . . ? C4 C5 C6 125.9(4) . . ? N2 C6 N4 108.7(3) . . ? N2 C6 C5 119.5(3) . . ? N4 C6 C5 131.8(3) . . ? N3 C7 N4 110.1(3) . . ? N3 C7 C8 130.2(3) . . ? N4 C7 C8 119.6(3) . . ? C9 C8 C7 118.8(4) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 120.8(4) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 121.0(4) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 N4 118.7(4) . . ? C10 C11 H11 120.6 . . ? N4 C11 H11 120.6 . . ? C20 N20 Fe1 174.8(3) . . ? N20 C20 S20 176.8(3) . . ? 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 N20 Fe1 N1 C1 -89.0(3) 3_755 . . . ? N20 Fe1 N1 C1 91.0(3) . . . . ? N2 Fe1 N1 C1 179.8(3) . . . . ? N2 Fe1 N1 C1 -0.2(3) 3_755 . . . ? N20 Fe1 N1 C5 82.5(3) 3_755 . . . ? N20 Fe1 N1 C5 -97.5(3) . . . . ? N2 Fe1 N1 C5 -8.7(2) . . . . ? N2 Fe1 N1 C5 171.3(2) 3_755 . . . ? C5 N1 C1 C2 -2.1(5) . . . . ? Fe1 N1 C1 C2 169.1(3) . . . . ? N20 Fe1 N2 C6 -81.2(3) 3_755 . . . ? N20 Fe1 N2 C6 98.8(3) . . . . ? N1 Fe1 N2 C6 -173.8(2) 3_755 . . . ? N1 Fe1 N2 C6 6.2(2) . . . . ? N20 Fe1 N2 N3 97.3(3) 3_755 . . . ? N20 Fe1 N2 N3 -82.7(3) . . . . ? N1 Fe1 N2 N3 4.7(3) 3_755 . . . ? N1 Fe1 N2 N3 -175.3(3) . . . . ? N1 C1 C2 C3 0.3(6) . . . . ? C6 N2 N3 C7 0.6(4) . . . . ? Fe1 N2 N3 C7 -178.0(3) . . . . ? C1 C2 C3 C4 0.6(7) . . . . ? C2 C3 C4 C5 0.4(7) . . . . ? C1 N1 C5 C4 3.2(5) . . . . ? Fe1 N1 C5 C4 -168.9(3) . . . . ? C1 N1 C5 C6 -178.5(3) . . . . ? Fe1 N1 C5 C6 9.3(4) . . . . ? C3 C4 C5 N1 -2.4(6) . . . . ? C3 C4 C5 C6 179.6(4) . . . . ? N3 N2 C6 N4 -0.2(4) . . . . ? Fe1 N2 C6 N4 178.6(2) . . . . ? N3 N2 C6 C5 177.8(3) . . . . ? Fe1 N2 C6 C5 -3.3(4) . . . . ? C11 N4 C6 N2 -179.0(3) . . . . ? C7 N4 C6 N2 -0.2(4) . . . . ? C11 N4 C6 C5 3.3(6) . . . . ? C7 N4 C6 C5 -177.9(4) . . . . ? N1 C5 C6 N2 -4.1(5) . . . . ? C4 C5 C6 N2 174.1(4) . . . . ? N1 C5 C6 N4 173.4(3) . . . . ? C4 C5 C6 N4 -8.4(6) . . . . ? N2 N3 C7 N4 -0.7(4) . . . . ? N2 N3 C7 C8 178.6(4) . . . . ? C6 N4 C7 N3 0.5(4) . . . . ? C11 N4 C7 N3 179.6(3) . . . . ? C6 N4 C7 C8 -178.8(3) . . . . ? C11 N4 C7 C8 0.2(5) . . . . ? N3 C7 C8 C9 -179.8(4) . . . . ? N4 C7 C8 C9 -0.6(5) . . . . ? C7 C8 C9 C10 0.5(6) . . . . ? C8 C9 C10 C11 0.0(6) . . . . ? C9 C10 C11 N4 -0.4(6) . . . . ? C6 N4 C11 C10 179.0(4) . . . . ? C7 N4 C11 C10 0.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.80 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.234 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.062 data_jmk107_1_2 _database_code_depnum_ccdc_archive 'CCDC 755113' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C24 H16 Fe N10 S2 ; _chemical_formula_sum 'C24 H16 Fe N10 S2' _chemical_formula_weight 564.44 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' S S 0.1246 0.1234 '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 8.2219(16) _cell_length_b 17.191(3) _cell_length_c 8.6719(17) _cell_angle_alpha 90.00 _cell_angle_beta 105.44(3) _cell_angle_gamma 90.00 _cell_volume 1181.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2008 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 26.07 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.852 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8686 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details ; March 2001 T Higashi ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Rigaku R-Axis SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15942 _diffrn_reflns_av_R_equivalents 0.0735 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 26.07 _reflns_number_total 2008 _reflns_number_gt 1573 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+1.2202P] 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 2008 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0796 _refine_ls_wR_factor_gt 0.0738 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 Fe1 Fe 0.0000 0.5000 0.5000 0.01340(16) Uani 1 2 d S . . N1 N -0.0348(3) 0.42263(13) 0.6719(3) 0.0153(5) Uani 1 1 d . . . N2 N 0.1581(3) 0.53865(13) 0.7012(3) 0.0150(5) Uani 1 1 d . . . N3 N 0.2571(3) 0.60193(13) 0.7368(3) 0.0168(5) Uani 1 1 d . . . N4 N 0.2865(3) 0.52914(13) 0.9696(3) 0.0149(5) Uani 1 1 d . . . C1 C -0.1420(3) 0.36470(16) 0.6451(4) 0.0175(6) Uani 1 1 d . . . H1 H -0.2196 0.3596 0.5427 0.021 Uiso 1 1 calc R . . C2 C -0.1448(4) 0.30856(17) 0.7673(4) 0.0223(7) Uani 1 1 d . . . H2 H -0.2256 0.2678 0.7435 0.027 Uiso 1 1 calc R . . C3 C -0.0318(4) 0.31202(18) 0.9212(4) 0.0248(7) Uani 1 1 d . . . H3 H -0.0323 0.2735 0.9996 0.030 Uiso 1 1 calc R . . C4 C 0.0773(4) 0.37247(17) 0.9526(4) 0.0228(7) Uani 1 1 d . . . H4 H 0.1552 0.3783 1.0547 0.027 Uiso 1 1 calc R . . C5 C 0.0719(3) 0.42740(16) 0.8273(3) 0.0156(6) Uani 1 1 d . . . C6 C 0.1742(3) 0.49548(16) 0.8384(3) 0.0155(6) Uani 1 1 d . . . C7 C 0.3352(3) 0.59569(16) 0.8992(3) 0.0163(6) Uani 1 1 d . . . C8 C 0.4552(3) 0.64387(16) 1.0013(3) 0.0187(7) Uani 1 1 d . . . H8 H 0.4949 0.6892 0.9601 0.022 Uiso 1 1 calc R . . C9 C 0.5170(3) 0.62482(16) 1.1660(4) 0.0194(6) Uani 1 1 d . . . H9 H 0.5970 0.6585 1.2331 0.023 Uiso 1 1 calc R . . C10 C 0.4635(4) 0.55680(17) 1.2348(4) 0.0209(7) Uani 1 1 d . . . H10 H 0.5063 0.5455 1.3454 0.025 Uiso 1 1 calc R . . C11 C 0.3512(3) 0.50973(17) 1.1382(3) 0.0181(6) Uani 1 1 d . . . H11 H 0.3140 0.4639 1.1797 0.022 Uiso 1 1 calc R . . N20 N 0.1557(3) 0.42890(13) 0.4521(3) 0.0162(5) Uani 1 1 d . . . C20 C 0.2413(3) 0.38290(16) 0.4187(3) 0.0163(6) Uani 1 1 d . . . S20 S 0.36601(10) 0.32093(5) 0.36985(10) 0.0279(2) 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 0.0095(3) 0.0128(3) 0.0174(3) 0.0003(2) 0.0029(2) -0.0007(2) N1 0.0108(11) 0.0138(12) 0.0211(14) -0.0029(10) 0.0038(10) 0.0003(9) N2 0.0112(11) 0.0118(12) 0.0211(13) 0.0010(10) 0.0028(10) -0.0002(9) N3 0.0107(11) 0.0162(13) 0.0209(14) 0.0009(11) -0.0005(10) -0.0032(9) N4 0.0106(11) 0.0147(12) 0.0179(13) -0.0007(10) 0.0010(10) -0.0018(9) C1 0.0120(14) 0.0182(15) 0.0233(17) -0.0039(13) 0.0064(13) -0.0031(12) C2 0.0182(15) 0.0187(16) 0.0311(18) -0.0012(14) 0.0087(14) -0.0069(12) C3 0.0268(17) 0.0225(17) 0.0259(18) 0.0057(14) 0.0083(15) -0.0060(13) C4 0.0207(15) 0.0232(17) 0.0221(17) 0.0023(14) 0.0015(14) -0.0048(13) C5 0.0125(13) 0.0152(15) 0.0182(16) -0.0012(12) 0.0028(12) 0.0015(11) C6 0.0105(12) 0.0148(14) 0.0214(16) -0.0002(13) 0.0043(12) -0.0001(11) C7 0.0119(14) 0.0156(15) 0.0218(17) 0.0001(13) 0.0052(12) 0.0005(11) C8 0.0145(15) 0.0161(15) 0.0253(17) -0.0020(13) 0.0051(14) -0.0038(11) C9 0.0145(14) 0.0182(16) 0.0246(17) -0.0051(13) 0.0033(13) -0.0032(12) C10 0.0187(16) 0.0255(17) 0.0170(16) -0.0014(13) 0.0021(13) 0.0006(13) C11 0.0155(13) 0.0202(16) 0.0186(16) 0.0028(13) 0.0046(12) 0.0011(12) N20 0.0111(12) 0.0169(13) 0.0198(14) 0.0010(11) 0.0024(10) -0.0035(10) C20 0.0158(14) 0.0136(15) 0.0187(16) 0.0026(12) 0.0033(12) -0.0009(12) S20 0.0304(4) 0.0280(5) 0.0272(5) 0.0037(4) 0.0107(4) 0.0156(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 Fe1 N20 1.894(2) 3_566 ? Fe1 N20 1.894(2) . ? Fe1 N2 1.992(2) 3_566 ? Fe1 N2 1.992(2) . ? Fe1 N1 2.074(2) 3_566 ? Fe1 N1 2.074(2) . ? N1 C1 1.309(3) . ? N1 C5 1.402(4) . ? N2 N3 1.344(3) . ? N2 C6 1.378(4) . ? N3 C7 1.388(4) . ? N4 C6 1.386(4) . ? N4 C7 1.404(3) . ? N4 C11 1.456(4) . ? C1 C2 1.438(4) . ? C1 H1 0.9500 . ? C2 C3 1.410(4) . ? C2 H2 0.9500 . ? C3 C4 1.352(4) . ? C3 H3 0.9500 . ? C4 C5 1.431(4) . ? C4 H4 0.9500 . ? C5 C6 1.430(4) . ? C7 C8 1.406(4) . ? C8 C9 1.421(4) . ? C8 H8 0.9500 . ? C9 C10 1.434(4) . ? C9 H9 0.9500 . ? C10 C11 1.341(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? N20 C20 1.146(3) . ? C20 S20 1.612(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 N20 Fe1 N20 180.0 3_566 . ? N20 Fe1 N2 94.92(9) 3_566 3_566 ? N20 Fe1 N2 85.08(9) . 3_566 ? N20 Fe1 N2 85.08(9) 3_566 . ? N20 Fe1 N2 94.92(9) . . ? N2 Fe1 N2 179.999(1) 3_566 . ? N20 Fe1 N1 88.54(9) 3_566 3_566 ? N20 Fe1 N1 91.47(9) . 3_566 ? N2 Fe1 N1 76.53(9) 3_566 3_566 ? N2 Fe1 N1 103.47(9) . 3_566 ? N20 Fe1 N1 91.46(9) 3_566 . ? N20 Fe1 N1 88.53(9) . . ? N2 Fe1 N1 103.47(9) 3_566 . ? N2 Fe1 N1 76.53(9) . . ? N1 Fe1 N1 180.0 3_566 . ? C1 N1 C5 115.8(2) . . ? C1 N1 Fe1 125.2(2) . . ? C5 N1 Fe1 118.86(17) . . ? N3 N2 C6 109.0(2) . . ? N3 N2 Fe1 133.20(18) . . ? C6 N2 Fe1 117.84(18) . . ? N2 N3 C7 105.0(2) . . ? C6 N4 C7 100.8(2) . . ? C6 N4 C11 135.6(2) . . ? C7 N4 C11 123.6(2) . . ? N1 C1 C2 121.5(3) . . ? N1 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? C3 C2 C1 122.2(3) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C4 C3 C2 117.2(3) . . ? C4 C3 H3 121.4 . . ? C2 C3 H3 121.4 . . ? C3 C4 C5 118.0(3) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? N1 C5 C6 108.6(2) . . ? N1 C5 C4 125.2(2) . . ? C6 C5 C4 126.2(3) . . ? N2 C6 N4 111.9(2) . . ? N2 C6 C5 117.6(2) . . ? N4 C6 C5 130.4(3) . . ? N3 C7 N4 113.3(2) . . ? N3 C7 C8 130.6(3) . . ? N4 C7 C8 116.1(2) . . ? C7 C8 C9 120.0(3) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C10 122.6(3) . . ? C8 C9 H9 118.7 . . ? C10 C9 H9 118.7 . . ? C11 C10 C9 118.0(3) . . ? C11 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? C10 C11 N4 119.7(3) . . ? C10 C11 H11 120.1 . . ? N4 C11 H11 120.1 . . ? C20 N20 Fe1 175.6(2) . . ? N20 C20 S20 177.7(3) . . ? 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 N20 Fe1 N1 C1 93.7(2) 3_566 . . . ? N20 Fe1 N1 C1 -86.3(2) . . . . ? N2 Fe1 N1 C1 -1.7(2) 3_566 . . . ? N2 Fe1 N1 C1 178.3(2) . . . . ? N20 Fe1 N1 C5 -91.69(19) 3_566 . . . ? N20 Fe1 N1 C5 88.31(19) . . . . ? N2 Fe1 N1 C5 172.89(18) 3_566 . . . ? N2 Fe1 N1 C5 -7.11(18) . . . . ? N20 Fe1 N2 N3 -81.3(2) 3_566 . . . ? N20 Fe1 N2 N3 98.7(2) . . . . ? N1 Fe1 N2 N3 6.0(2) 3_566 . . . ? N1 Fe1 N2 N3 -174.0(2) . . . . ? N20 Fe1 N2 C6 97.43(19) 3_566 . . . ? N20 Fe1 N2 C6 -82.57(19) . . . . ? N1 Fe1 N2 C6 -175.27(18) 3_566 . . . ? N1 Fe1 N2 C6 4.73(18) . . . . ? C6 N2 N3 C7 0.5(3) . . . . ? Fe1 N2 N3 C7 179.31(18) . . . . ? C5 N1 C1 C2 -1.9(4) . . . . ? Fe1 N1 C1 C2 172.88(19) . . . . ? N1 C1 C2 C3 -0.9(4) . . . . ? C1 C2 C3 C4 2.3(4) . . . . ? C2 C3 C4 C5 -1.0(4) . . . . ? C1 N1 C5 C6 -177.2(2) . . . . ? Fe1 N1 C5 C6 7.7(3) . . . . ? C1 N1 C5 C4 3.3(4) . . . . ? Fe1 N1 C5 C4 -171.8(2) . . . . ? C3 C4 C5 N1 -1.9(4) . . . . ? C3 C4 C5 C6 178.7(3) . . . . ? N3 N2 C6 N4 -0.4(3) . . . . ? Fe1 N2 C6 N4 -179.40(16) . . . . ? N3 N2 C6 C5 176.9(2) . . . . ? Fe1 N2 C6 C5 -2.1(3) . . . . ? C7 N4 C6 N2 0.1(3) . . . . ? C11 N4 C6 N2 -179.5(3) . . . . ? C7 N4 C6 C5 -176.8(3) . . . . ? C11 N4 C6 C5 3.7(5) . . . . ? N1 C5 C6 N2 -3.6(3) . . . . ? C4 C5 C6 N2 175.9(2) . . . . ? N1 C5 C6 N4 173.1(2) . . . . ? C4 C5 C6 N4 -7.4(5) . . . . ? N2 N3 C7 N4 -0.5(3) . . . . ? N2 N3 C7 C8 178.2(3) . . . . ? C6 N4 C7 N3 0.3(3) . . . . ? C11 N4 C7 N3 179.9(2) . . . . ? C6 N4 C7 C8 -178.6(2) . . . . ? C11 N4 C7 C8 1.0(4) . . . . ? N3 C7 C8 C9 180.0(3) . . . . ? N4 C7 C8 C9 -1.3(4) . . . . ? C7 C8 C9 C10 0.8(4) . . . . ? C8 C9 C10 C11 0.3(4) . . . . ? C9 C10 C11 N4 -0.7(4) . . . . ? C6 N4 C11 C10 179.5(3) . . . . ? C7 N4 C11 C10 0.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.858 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.858 _refine_diff_density_max 0.325 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.070 data_jmk76_3_2 _database_code_depnum_ccdc_archive 'CCDC 755114' _audit_update_record ; 2009-04-29 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C11 H8 N4 ; _chemical_formula_sum 'C11 H8 N4' _chemical_formula_weight 196.21 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' _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 7.6616(15) _cell_length_b 7.6757(15) _cell_length_c 17.818(4) _cell_angle_alpha 80.28(3) _cell_angle_beta 89.82(3) _cell_angle_gamma 62.16(3) _cell_volume 909.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 5808 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 31.02 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9553 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details ; March 2001 T Higashi ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 'Rigaku R-Axis SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14620 _diffrn_reflns_av_R_equivalents 0.0744 _diffrn_reflns_av_sigmaI/netI 0.0715 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 31.02 _reflns_number_total 4122 _reflns_number_gt 2523 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1123P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4122 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1074 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.2045 _refine_ls_wR_factor_gt 0.1619 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 N1 N 0.6063(3) 0.2925(4) 0.58700(12) 0.0283(6) Uani 1 1 d . . . N2 N 0.2231(3) 0.3651(4) 0.42500(12) 0.0294(6) Uani 1 1 d . . . N3 N 0.2548(3) 0.2731(4) 0.35869(12) 0.0297(6) Uani 1 1 d . . . N4 N 0.5491(3) 0.1463(3) 0.43860(11) 0.0241(5) Uani 1 1 d . . . C1 C 0.6192(4) 0.3681(4) 0.65500(14) 0.0303(7) Uani 1 1 d . . . H1 H 0.7471 0.3220 0.6794 0.036 Uiso 1 1 calc R . . C2 C 0.4584(4) 0.5024(4) 0.68657(14) 0.0294(6) Uani 1 1 d . . . H2 H 0.4720 0.5472 0.7317 0.035 Uiso 1 1 calc R . . C3 C 0.2666(4) 0.5708(4) 0.64607(15) 0.0318(7) Uani 1 1 d . . . H3 H 0.1508 0.6645 0.6650 0.038 Uiso 1 1 calc R . . C4 C 0.2462(4) 0.4987(4) 0.57597(14) 0.0268(6) Uani 1 1 d . . . H4 H 0.1193 0.5436 0.5507 0.032 Uiso 1 1 calc R . . C5 C 0.4175(4) 0.3633(4) 0.54804(13) 0.0244(6) Uani 1 1 d . . . C6 C 0.3972(4) 0.2909(4) 0.47263(14) 0.0247(6) Uani 1 1 d . . . C7 C 0.4527(4) 0.1414(4) 0.36665(14) 0.0275(6) Uani 1 1 d . . . C8 C 0.5676(4) 0.0108(4) 0.31541(15) 0.0312(7) Uani 1 1 d . . . H8 H 0.5100 0.0083 0.2687 0.037 Uiso 1 1 calc R . . C9 C 0.7699(4) -0.1122(4) 0.33924(15) 0.0322(7) Uani 1 1 d . . . H9 H 0.8511 -0.2012 0.3076 0.039 Uiso 1 1 calc R . . C10 C 0.8642(4) -0.1085(4) 0.41371(15) 0.0317(7) Uani 1 1 d . . . H10 H 1.0014 -0.1963 0.4272 0.038 Uiso 1 1 calc R . . C11 C 0.7555(4) 0.0193(4) 0.46253(14) 0.0255(6) Uani 1 1 d . . . H11 H 0.8143 0.0224 0.5088 0.031 Uiso 1 1 calc R . . N21 N 0.8921(3) 0.8931(3) -0.08658(12) 0.0271(5) Uani 1 1 d . . . N22 N 1.2802(3) 0.5812(4) 0.07806(12) 0.0298(6) Uani 1 1 d . . . N23 N 1.2548(3) 0.5087(4) 0.14380(12) 0.0303(6) Uani 1 1 d . . . N24 N 0.9573(3) 0.6870(3) 0.06401(11) 0.0233(5) Uani 1 1 d . . . C21 C 0.8743(4) 0.9754(4) -0.15648(15) 0.0316(7) Uani 1 1 d . . . H21 H 0.7486 1.0512 -0.1848 0.038 Uiso 1 1 calc R . . C22 C 1.0348(4) 0.9509(4) -0.18676(15) 0.0316(7) Uani 1 1 d . . . H22 H 1.0276 1.0088 -0.2389 0.038 Uiso 1 1 calc R . . C23 C 1.2258(4) 0.8373(4) -0.14335(15) 0.0312(7) Uani 1 1 d . . . H23 H 1.3400 0.8235 -0.1684 0.037 Uiso 1 1 calc R . . C24 C 1.2494(4) 0.7522(4) -0.07092(15) 0.0285(6) Uani 1 1 d . . . H24 H 1.3735 0.6788 -0.0413 0.034 Uiso 1 1 calc R . . C25 C 1.0796(4) 0.7818(4) -0.04510(14) 0.0238(6) Uani 1 1 d . . . C26 C 1.1055(4) 0.6863(4) 0.03079(14) 0.0253(6) Uani 1 1 d . . . C27 C 1.0599(4) 0.5745(4) 0.13506(13) 0.0255(6) Uani 1 1 d . . . C28 C 0.9518(4) 0.5462(4) 0.18534(14) 0.0279(6) Uani 1 1 d . . . H28 H 1.0052 0.4717 0.2354 0.033 Uiso 1 1 calc R . . C29 C 0.7506(4) 0.6315(4) 0.16216(15) 0.0295(6) Uani 1 1 d . . . H29 H 0.6701 0.6107 0.1996 0.035 Uiso 1 1 calc R . . C30 C 0.6495(4) 0.7471(4) 0.08868(14) 0.0294(6) Uani 1 1 d . . . H30 H 0.5106 0.8004 0.0784 0.035 Uiso 1 1 calc R . . C31 C 0.7529(4) 0.7723(4) 0.04051(14) 0.0257(6) Uani 1 1 d . . . H31 H 0.6997 0.8449 -0.0098 0.031 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 N1 0.0257(12) 0.0354(14) 0.0235(11) 0.0036(9) 0.0024(9) -0.0172(11) N2 0.0256(12) 0.0375(14) 0.0258(11) 0.0016(9) 0.0034(9) -0.0180(11) N3 0.0313(13) 0.0357(14) 0.0248(11) -0.0005(9) 0.0034(9) -0.0197(11) N4 0.0232(11) 0.0298(12) 0.0221(10) 0.0017(9) 0.0043(8) -0.0170(10) C1 0.0292(15) 0.0387(17) 0.0233(13) 0.0034(11) 0.0013(10) -0.0193(13) C2 0.0376(16) 0.0347(16) 0.0213(12) -0.0010(11) 0.0057(11) -0.0229(14) C3 0.0329(16) 0.0353(17) 0.0280(14) -0.0001(11) 0.0092(11) -0.0188(14) C4 0.0228(13) 0.0288(15) 0.0286(13) 0.0014(11) 0.0041(10) -0.0143(12) C5 0.0234(13) 0.0288(15) 0.0227(12) 0.0021(10) 0.0037(10) -0.0159(12) C6 0.0234(13) 0.0272(15) 0.0233(12) 0.0017(10) 0.0037(10) -0.0140(12) C7 0.0277(14) 0.0362(16) 0.0231(12) 0.0029(11) 0.0014(10) -0.0214(13) C8 0.0364(16) 0.0363(17) 0.0281(14) -0.0040(11) 0.0052(11) -0.0238(14) C9 0.0393(17) 0.0332(16) 0.0319(14) -0.0086(12) 0.0156(12) -0.0228(14) C10 0.0262(15) 0.0350(17) 0.0339(14) -0.0004(12) 0.0074(11) -0.0166(13) C11 0.0234(13) 0.0237(14) 0.0288(13) 0.0006(10) 0.0031(10) -0.0124(12) N21 0.0279(12) 0.0299(13) 0.0245(11) -0.0012(9) 0.0055(9) -0.0159(10) N22 0.0271(12) 0.0347(14) 0.0255(11) -0.0013(9) 0.0039(9) -0.0143(11) N23 0.0266(13) 0.0367(14) 0.0245(11) 0.0007(10) 0.0023(9) -0.0147(11) N24 0.0238(11) 0.0253(12) 0.0204(10) -0.0014(8) 0.0027(8) -0.0122(10) C21 0.0317(15) 0.0386(17) 0.0251(13) -0.0004(11) 0.0023(11) -0.0189(14) C22 0.0390(17) 0.0314(16) 0.0256(13) -0.0014(11) 0.0090(11) -0.0190(14) C23 0.0342(16) 0.0309(16) 0.0372(15) -0.0101(12) 0.0157(12) -0.0215(14) C24 0.0259(14) 0.0290(15) 0.0296(13) -0.0039(11) 0.0054(10) -0.0128(12) C25 0.0262(14) 0.0239(14) 0.0247(12) -0.0054(10) 0.0066(10) -0.0145(12) C26 0.0255(14) 0.0266(15) 0.0264(13) -0.0049(10) 0.0048(10) -0.0145(12) C27 0.0284(14) 0.0259(15) 0.0197(12) -0.0019(10) 0.0004(10) -0.0117(12) C28 0.0365(16) 0.0303(15) 0.0178(12) -0.0007(10) 0.0043(10) -0.0178(13) C29 0.0347(16) 0.0298(15) 0.0248(13) -0.0021(10) 0.0067(11) -0.0171(13) C30 0.0273(15) 0.0346(16) 0.0273(13) -0.0021(11) 0.0049(11) -0.0167(13) C31 0.0239(14) 0.0281(15) 0.0242(12) 0.0001(10) 0.0000(10) -0.0131(12) _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 N1 C5 1.419(3) . ? N1 C1 1.452(4) . ? N2 C6 1.400(3) . ? N2 N3 1.440(3) . ? N3 C7 1.365(4) . ? N4 C6 1.404(3) . ? N4 C11 1.434(3) . ? N4 C7 1.496(3) . ? C1 C2 1.379(4) . ? C2 C3 1.454(4) . ? C3 C4 1.486(4) . ? C4 C5 1.395(4) . ? C5 C6 1.573(4) . ? C7 C8 1.447(4) . ? C8 C9 1.406(4) . ? C9 C10 1.524(4) . ? C10 C11 1.391(4) . ? N21 C21 1.274(3) . ? N21 C25 1.410(3) . ? N22 N23 1.264(3) . ? N22 C26 1.386(3) . ? N23 C27 1.334(3) . ? N24 C26 1.277(3) . ? N24 C27 1.403(3) . ? N24 C31 1.418(3) . ? C21 C22 1.285(4) . ? C22 C23 1.445(4) . ? C23 C24 1.316(4) . ? C24 C25 1.308(4) . ? C25 C26 1.392(3) . ? C27 C28 1.278(3) . ? C28 C29 1.395(4) . ? C29 C30 1.440(4) . ? C30 C31 1.219(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 C5 N1 C1 119.0(2) . . ? C6 N2 N3 112.5(2) . . ? C7 N3 N2 104.1(2) . . ? C6 N4 C11 131.4(2) . . ? C6 N4 C7 105.6(2) . . ? C11 N4 C7 123.0(2) . . ? C2 C1 N1 124.5(2) . . ? C1 C2 C3 115.4(3) . . ? C2 C3 C4 122.0(3) . . ? C5 C4 C3 118.5(2) . . ? C4 C5 N1 120.6(2) . . ? C4 C5 C6 118.7(2) . . ? N1 C5 C6 120.7(2) . . ? N2 C6 N4 106.8(2) . . ? N2 C6 C5 126.0(2) . . ? N4 C6 C5 127.2(2) . . ? N3 C7 C8 128.2(3) . . ? N3 C7 N4 110.9(2) . . ? C8 C7 N4 120.8(2) . . ? C9 C8 C7 115.6(3) . . ? C8 C9 C10 122.7(3) . . ? C11 C10 C9 122.0(3) . . ? C10 C11 N4 115.8(2) . . ? C21 N21 C25 121.0(2) . . ? N23 N22 C26 112.3(2) . . ? N22 N23 C27 99.5(2) . . ? C26 N24 C27 97.2(2) . . ? C26 N24 C31 133.5(2) . . ? C27 N24 C31 129.3(2) . . ? N21 C21 C22 116.8(3) . . ? C21 C22 C23 121.6(2) . . ? C24 C23 C22 123.3(2) . . ? C25 C24 C23 111.1(3) . . ? C24 C25 C26 111.0(2) . . ? C24 C25 N21 126.3(2) . . ? C26 C25 N21 122.7(2) . . ? N24 C26 N22 112.4(2) . . ? N24 C26 C25 119.8(2) . . ? N22 C26 C25 127.7(2) . . ? N22 C26 C27 68.63(15) . . ? C25 C26 C27 163.6(2) . . ? C28 C27 N23 126.8(2) . . ? C28 C27 N24 114.6(2) . . ? N23 C27 N24 118.5(2) . . ? C28 C27 C26 153.6(2) . . ? N23 C27 C26 79.51(16) . . ? C27 C28 C29 115.9(2) . . ? C28 C29 C30 128.2(2) . . ? C31 C30 C29 115.9(3) . . ? C30 C31 N24 116.1(2) . . ? 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 C6 N2 N3 C7 -0.3(3) . . . . ? C5 N1 C1 C2 1.8(4) . . . . ? N1 C1 C2 C3 -1.1(4) . . . . ? C1 C2 C3 C4 0.6(4) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C3 C4 C5 N1 1.7(3) . . . . ? C3 C4 C5 C6 -178.4(2) . . . . ? C1 N1 C5 C4 -2.1(3) . . . . ? C1 N1 C5 C6 178.0(2) . . . . ? N3 N2 C6 N4 -0.2(3) . . . . ? N3 N2 C6 C5 177.7(2) . . . . ? C11 N4 C6 N2 -178.4(2) . . . . ? C7 N4 C6 N2 0.5(2) . . . . ? C11 N4 C6 C5 3.7(4) . . . . ? C7 N4 C6 C5 -177.3(2) . . . . ? C4 C5 C6 N2 7.2(4) . . . . ? N1 C5 C6 N2 -172.9(2) . . . . ? C4 C5 C6 N4 -175.3(2) . . . . ? N1 C5 C6 N4 4.6(4) . . . . ? N2 N3 C7 C8 -178.5(2) . . . . ? N2 N3 C7 N4 0.6(3) . . . . ? C6 N4 C7 N3 -0.8(3) . . . . ? C11 N4 C7 N3 178.3(2) . . . . ? C6 N4 C7 C8 178.5(2) . . . . ? C11 N4 C7 C8 -2.4(3) . . . . ? N3 C7 C8 C9 -179.0(2) . . . . ? N4 C7 C8 C9 1.9(4) . . . . ? C7 C8 C9 C10 -0.5(4) . . . . ? C8 C9 C10 C11 -0.8(4) . . . . ? C9 C10 C11 N4 0.4(4) . . . . ? C6 N4 C11 C10 180.0(2) . . . . ? C7 N4 C11 C10 1.1(3) . . . . ? C26 N22 N23 C27 -0.5(3) . . . . ? C25 N21 C21 C22 0.3(4) . . . . ? N21 C21 C22 C23 -0.7(5) . . . . ? C21 C22 C23 C24 0.0(5) . . . . ? C22 C23 C24 C25 1.0(4) . . . . ? C23 C24 C25 C26 178.1(3) . . . . ? C23 C24 C25 N21 -1.4(4) . . . . ? C21 N21 C25 C24 0.8(5) . . . . ? C21 N21 C25 C26 -178.6(3) . . . . ? C27 N24 C26 N22 0.4(3) . . . . ? C31 N24 C26 N22 179.7(3) . . . . ? C27 N24 C26 C25 179.4(3) . . . . ? C31 N24 C26 C25 -1.3(5) . . . . ? C31 N24 C26 C27 179.4(4) . . . . ? N23 N22 C26 N24 0.1(4) . . . . ? N23 N22 C26 C25 -178.8(3) . . . . ? N23 N22 C26 C27 0.4(2) . . . . ? C24 C25 C26 N24 -175.1(3) . . . . ? N21 C25 C26 N24 4.4(4) . . . . ? C24 C25 C26 N22 3.7(4) . . . . ? N21 C25 C26 N22 -176.8(3) . . . . ? C24 C25 C26 C27 -173.6(7) . . . . ? N21 C25 C26 C27 6.0(10) . . . . ? N22 N23 C27 C28 -179.2(3) . . . . ? N22 N23 C27 N24 0.8(3) . . . . ? N22 N23 C27 C26 0.3(2) . . . . ? C26 N24 C27 C28 179.2(3) . . . . ? C31 N24 C27 C28 -0.2(4) . . . . ? C26 N24 C27 N23 -0.8(3) . . . . ? C31 N24 C27 N23 179.8(3) . . . . ? C31 N24 C27 C26 -179.4(4) . . . . ? N24 C26 C27 C28 -1.6(6) . . . . ? N22 C26 C27 C28 178.8(6) . . . . ? C25 C26 C27 C28 -3.6(12) . . . . ? N24 C26 C27 N23 179.3(3) . . . . ? N22 C26 C27 N23 -0.32(19) . . . . ? C25 C26 C27 N23 177.3(8) . . . . ? N22 C26 C27 N24 -179.6(3) . . . . ? C25 C26 C27 N24 -2.0(8) . . . . ? N23 C27 C28 C29 179.7(3) . . . . ? N24 C27 C28 C29 -0.3(4) . . . . ? C26 C27 C28 C29 0.8(7) . . . . ? C27 C28 C29 C30 0.1(5) . . . . ? C28 C29 C30 C31 0.6(5) . . . . ? C29 C30 C31 N24 -0.9(4) . . . . ? C26 N24 C31 C30 -178.3(3) . . . . ? C27 N24 C31 C30 0.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.710 _diffrn_reflns_theta_full 31.02 _diffrn_measured_fraction_theta_full 0.710 _refine_diff_density_max 0.321 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.077 data_jmk_afp03_nils _database_code_depnum_ccdc_archive 'CCDC 755115' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C44 H32 Co N16, 2(Cl O4), H2 O ; _chemical_formula_sum 'C44 H34 Cl2 Co N16 O9' _chemical_formula_weight 1060.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3006(15) _cell_length_b 12.248(2) _cell_length_c 13.898(3) _cell_angle_alpha 70.66(3) _cell_angle_beta 85.82(3) _cell_angle_gamma 77.88(3) _cell_volume 1146.4(4) _cell_formula_units_Z 1 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 2965 _cell_measurement_theta_min 1.80 _cell_measurement_theta_max 25.01 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.536 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 543 _exptl_absorpt_coefficient_mu 0.567 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7725 _exptl_absorpt_correction_T_max 0.9299 _exptl_absorpt_process_details ; March 2001 T Higashi ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 'Rigaku R-Axis SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10053 _diffrn_reflns_av_R_equivalents 0.0961 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2965 _reflns_number_gt 2666 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1103P)^2^+4.1645P] 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 2965 _refine_ls_number_parameters 331 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0945 _refine_ls_R_factor_gt 0.0839 _refine_ls_wR_factor_ref 0.2195 _refine_ls_wR_factor_gt 0.2128 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 2.205 _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 0.5000 0.5000 0.5000 0.0157(7) Uani 1 2 d S . . N1 N 0.6421(12) 0.5428(7) 0.3571(6) 0.0170(18) Uani 1 1 d . . . N2 N 0.3246(13) 0.4698(8) 0.4022(7) 0.0188(19) Uani 1 1 d . . . N3 N 0.1781(13) 0.4120(8) 0.4210(7) 0.022(2) Uani 1 1 d . . . N4 N 0.3036(13) 0.4144(7) 0.2696(7) 0.0192(19) Uani 1 1 d . . . C1 C 0.7879(16) 0.5979(10) 0.3376(9) 0.023(2) Uani 1 1 d . . . H1 H 0.8373 0.6147 0.3906 0.028 Uiso 1 1 calc R . . C2 C 0.8683(17) 0.6310(11) 0.2402(9) 0.027(3) Uani 1 1 d . . . H2 H 0.9713 0.6687 0.2279 0.033 Uiso 1 1 calc R . . C3 C 0.7937(19) 0.6072(12) 0.1629(9) 0.033(3) Uani 1 1 d . . . H3 H 0.8457 0.6291 0.0970 0.039 Uiso 1 1 calc R . . C4 C 0.6415(15) 0.5507(10) 0.1820(8) 0.023(2) Uani 1 1 d . . . H4 H 0.5900 0.5329 0.1302 0.028 Uiso 1 1 calc R . . C5 C 0.5691(15) 0.5218(9) 0.2798(8) 0.019(2) Uani 1 1 d . . . C6 C 0.4012(15) 0.4699(9) 0.3136(8) 0.019(2) Uani 1 1 d . . . C7 C 0.1639(16) 0.3797(9) 0.3406(8) 0.020(2) Uani 1 1 d . . . C8 C 0.0337(17) 0.3209(10) 0.3187(9) 0.027(3) Uani 1 1 d . . . H8 H -0.0627 0.2983 0.3651 0.032 Uiso 1 1 calc R . . C9 C 0.0511(18) 0.2977(11) 0.2282(10) 0.031(3) Uani 1 1 d . . . H9 H -0.0359 0.2602 0.2113 0.037 Uiso 1 1 calc R . . C10 C 0.1988(19) 0.3295(11) 0.1601(9) 0.032(3) Uani 1 1 d . . . H10 H 0.2103 0.3102 0.0996 0.039 Uiso 1 1 calc R . . C11 C 0.3247(19) 0.3870(10) 0.1791(8) 0.028(3) Uani 1 1 d . . . H11 H 0.4224 0.4076 0.1331 0.034 Uiso 1 1 calc R . . N21 N 0.2339(16) 1.0476(8) 0.5224(8) 0.031(2) Uani 1 1 d . . . N22 N 0.3772(15) 0.7376(8) 0.5422(7) 0.024(2) Uani 1 1 d . . . N23 N 0.3713(13) 0.6898(7) 0.4672(7) 0.020(2) Uani 1 1 d . . . N24 N 0.2619(13) 0.8837(8) 0.4051(7) 0.020(2) Uani 1 1 d . . . C21 C 0.231(2) 1.1174(11) 0.5792(10) 0.036(3) Uani 1 1 d . . . H21 H 0.1883 1.1990 0.5485 0.044 Uiso 1 1 calc R . . C22 C 0.286(2) 1.0778(11) 0.6798(10) 0.036(3) Uani 1 1 d . . . H22 H 0.2817 1.1310 0.7160 0.043 Uiso 1 1 calc R . . C23 C 0.349(2) 0.9588(12) 0.7258(10) 0.036(3) Uani 1 1 d . . . H23 H 0.3859 0.9291 0.7945 0.043 Uiso 1 1 calc R . . C24 C 0.356(2) 0.8825(11) 0.6691(10) 0.033(3) Uani 1 1 d . . . H24 H 0.3975 0.8007 0.6987 0.039 Uiso 1 1 calc R . . C25 C 0.3003(16) 0.9314(10) 0.5677(8) 0.021(2) Uani 1 1 d . . . C26 C 0.3110(16) 0.8525(9) 0.5064(8) 0.021(2) Uani 1 1 d . . . C27 C 0.3030(16) 0.7781(9) 0.3832(9) 0.021(2) Uani 1 1 d . . . C28 C 0.2681(18) 0.7794(10) 0.2838(9) 0.029(3) Uani 1 1 d . . . H28 H 0.2944 0.7094 0.2671 0.035 Uiso 1 1 calc R . . C29 C 0.1953(19) 0.8847(11) 0.2130(9) 0.033(3) Uani 1 1 d . . . H29 H 0.1710 0.8872 0.1467 0.039 Uiso 1 1 calc R . . C30 C 0.156(2) 0.9904(11) 0.2384(10) 0.037(3) Uani 1 1 d . . . H30 H 0.1050 1.0619 0.1886 0.044 Uiso 1 1 calc R . . C31 C 0.1901(17) 0.9906(10) 0.3329(9) 0.027(3) Uani 1 1 d . . . H31 H 0.1658 1.0611 0.3489 0.032 Uiso 1 1 calc R . . Cl1 Cl 0.2486(5) 0.7132(3) -0.0028(2) 0.0373(9) Uani 1 1 d . . . O1 O 0.2299(14) 0.6730(10) 0.1052(7) 0.045(3) Uani 1 1 d . . . O2 O 0.086(2) 0.7961(14) -0.0465(12) 0.093(5) Uani 1 1 d . . . O3 O 0.272(3) 0.6159(14) -0.0407(11) 0.089(5) Uani 1 1 d . . . O4 O 0.413(2) 0.7605(16) -0.0283(12) 0.093(5) Uani 1 1 d . . . O5 O 0.3876(7) 1.053(2) 0.9611(15) 0.130(19) Uani 0.50 1 d PD . . H5A H 0.4041 1.0736 1.0081 0.156 Uiso 0.50 1 d PD . . H5B H 0.2847 1.0642 0.9389 0.156 Uiso 0.50 1 d PD . . 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 0.0226(11) 0.0109(10) 0.0146(10) -0.0048(8) 0.0006(8) -0.0046(8) N1 0.025(5) 0.013(4) 0.013(4) -0.003(3) 0.003(3) -0.005(3) N2 0.023(5) 0.014(4) 0.018(4) -0.005(4) -0.003(4) 0.000(3) N3 0.024(5) 0.017(4) 0.025(5) -0.004(4) 0.000(4) -0.008(4) N4 0.029(5) 0.011(4) 0.017(4) -0.003(3) -0.004(4) -0.002(3) C1 0.024(6) 0.017(5) 0.028(6) -0.006(5) 0.000(5) -0.006(4) C2 0.027(6) 0.027(6) 0.028(6) -0.007(5) 0.007(5) -0.011(5) C3 0.040(7) 0.035(7) 0.019(6) -0.003(5) 0.006(5) -0.013(5) C4 0.024(6) 0.027(6) 0.017(5) -0.004(5) -0.002(4) -0.004(4) C5 0.024(6) 0.013(5) 0.021(5) -0.006(4) -0.001(4) -0.005(4) C6 0.024(5) 0.015(5) 0.017(5) -0.004(4) -0.003(4) -0.007(4) C7 0.030(6) 0.012(5) 0.018(5) -0.004(4) -0.001(5) -0.005(4) C8 0.030(6) 0.022(6) 0.031(6) -0.010(5) 0.001(5) -0.009(5) C9 0.037(7) 0.023(6) 0.035(7) -0.008(5) -0.010(6) -0.012(5) C10 0.050(8) 0.028(6) 0.022(6) -0.012(5) -0.005(5) -0.007(6) C11 0.045(7) 0.026(6) 0.016(5) -0.009(5) 0.002(5) -0.009(5) N21 0.048(6) 0.013(5) 0.031(5) -0.007(4) 0.000(5) -0.005(4) N22 0.038(6) 0.014(4) 0.020(5) -0.004(4) -0.002(4) -0.001(4) N23 0.026(5) 0.012(4) 0.021(5) -0.004(4) -0.004(4) 0.000(4) N24 0.026(5) 0.010(4) 0.024(5) -0.004(4) 0.000(4) -0.003(3) C21 0.056(8) 0.014(6) 0.037(7) -0.009(5) 0.009(6) -0.006(5) C22 0.053(8) 0.024(7) 0.039(7) -0.019(6) 0.005(6) -0.010(6) C23 0.050(8) 0.034(7) 0.026(6) -0.019(6) -0.001(6) 0.003(6) C24 0.047(8) 0.014(6) 0.037(7) -0.009(5) -0.006(6) 0.001(5) C25 0.024(5) 0.018(5) 0.023(5) -0.008(4) 0.002(4) -0.004(4) C26 0.026(6) 0.013(5) 0.024(5) -0.005(4) 0.004(5) -0.004(4) C27 0.024(5) 0.014(5) 0.024(6) -0.006(5) 0.000(4) -0.003(4) C28 0.040(7) 0.017(6) 0.031(6) -0.012(5) -0.006(5) 0.001(5) C29 0.048(8) 0.022(6) 0.026(6) -0.006(5) -0.009(6) 0.001(5) C30 0.052(8) 0.020(6) 0.031(7) -0.002(5) -0.012(6) 0.001(5) C31 0.036(7) 0.012(5) 0.032(6) -0.006(5) 0.000(5) -0.004(5) Cl1 0.049(2) 0.0425(19) 0.0220(15) -0.0085(13) -0.0003(13) -0.0146(15) O1 0.047(6) 0.063(7) 0.022(4) -0.012(4) 0.001(4) -0.008(5) O2 0.107(12) 0.076(10) 0.075(9) -0.018(8) -0.042(9) 0.033(9) O3 0.134(14) 0.079(10) 0.069(9) -0.053(8) 0.007(9) -0.010(9) O4 0.090(11) 0.097(12) 0.081(10) 0.005(9) 0.007(9) -0.054(9) O5 0.22(5) 0.11(3) 0.12(3) -0.09(3) 0.13(3) -0.12(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 N2 2.100(9) 2_666 ? Co1 N2 2.100(9) . ? Co1 N1 2.129(8) 2_666 ? Co1 N1 2.129(8) . ? Co1 N23 2.222(8) . ? Co1 N23 2.222(8) 2_666 ? N1 C1 1.342(14) . ? N1 C5 1.352(14) . ? N2 C6 1.314(14) . ? N2 N3 1.367(13) . ? N3 C7 1.321(15) . ? N4 C6 1.373(14) . ? N4 C11 1.396(14) . ? N4 C7 1.397(15) . ? C1 C2 1.400(17) . ? C2 C3 1.377(18) . ? C3 C4 1.394(17) . ? C4 C5 1.381(16) . ? C5 C6 1.474(14) . ? C7 C8 1.410(16) . ? C8 C9 1.371(18) . ? C9 C10 1.412(19) . ? C10 C11 1.357(18) . ? N21 C21 1.338(17) . ? N21 C25 1.348(15) . ? N22 C26 1.322(15) . ? N22 N23 1.361(13) . ? N23 C27 1.343(14) . ? N24 C31 1.383(14) . ? N24 C26 1.384(15) . ? N24 C27 1.393(15) . ? C21 C22 1.380(19) . ? C22 C23 1.373(19) . ? C23 C24 1.399(18) . ? C24 C25 1.391(17) . ? C25 C26 1.472(16) . ? C27 C28 1.418(16) . ? C28 C29 1.364(17) . ? C29 C30 1.420(18) . ? C30 C31 1.355(18) . ? Cl1 O2 1.411(14) . ? Cl1 O4 1.415(15) . ? Cl1 O1 1.421(9) . ? Cl1 O3 1.430(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Co1 N2 179.999(2) 2_666 . ? N2 Co1 N1 76.5(3) 2_666 2_666 ? N2 Co1 N1 103.5(3) . 2_666 ? N2 Co1 N1 103.5(3) 2_666 . ? N2 Co1 N1 76.5(3) . . ? N1 Co1 N1 179.999(2) 2_666 . ? N2 Co1 N23 84.5(3) 2_666 . ? N2 Co1 N23 95.5(3) . . ? N1 Co1 N23 90.5(3) 2_666 . ? N1 Co1 N23 89.5(3) . . ? N2 Co1 N23 95.5(3) 2_666 2_666 ? N2 Co1 N23 84.5(3) . 2_666 ? N1 Co1 N23 89.5(3) 2_666 2_666 ? N1 Co1 N23 90.5(3) . 2_666 ? N23 Co1 N23 180.0(5) . 2_666 ? C1 N1 C5 118.8(9) . . ? C1 N1 Co1 123.9(7) . . ? C5 N1 Co1 117.1(7) . . ? C6 N2 N3 109.8(9) . . ? C6 N2 Co1 114.0(7) . . ? N3 N2 Co1 131.9(7) . . ? C7 N3 N2 106.6(9) . . ? C6 N4 C11 133.8(10) . . ? C6 N4 C7 104.5(9) . . ? C11 N4 C7 121.6(10) . . ? N1 C1 C2 121.5(11) . . ? C3 C2 C1 118.8(11) . . ? C2 C3 C4 120.2(11) . . ? C5 C4 C3 117.5(10) . . ? N1 C5 C4 123.2(10) . . ? N1 C5 C6 110.9(9) . . ? C4 C5 C6 125.8(10) . . ? N2 C6 N4 109.1(9) . . ? N2 C6 C5 119.4(9) . . ? N4 C6 C5 131.5(10) . . ? N3 C7 N4 110.0(9) . . ? N3 C7 C8 130.2(11) . . ? N4 C7 C8 119.8(10) . . ? C9 C8 C7 118.3(11) . . ? C8 C9 C10 120.5(11) . . ? C11 C10 C9 122.2(12) . . ? C10 C11 N4 117.5(11) . . ? C21 N21 C25 116.5(11) . . ? C26 N22 N23 109.2(9) . . ? C27 N23 N22 107.5(8) . . ? C27 N23 Co1 134.6(8) . . ? N22 N23 Co1 117.4(6) . . ? C31 N24 C26 132.9(10) . . ? C31 N24 C27 122.4(10) . . ? C26 N24 C27 104.7(9) . . ? N21 C21 C22 124.4(12) . . ? C23 C22 C21 118.5(12) . . ? C22 C23 C24 119.1(12) . . ? C25 C24 C23 118.0(11) . . ? N21 C25 C24 123.4(11) . . ? N21 C25 C26 117.9(10) . . ? C24 C25 C26 118.7(10) . . ? N22 C26 N24 109.5(10) . . ? N22 C26 C25 123.1(10) . . ? N24 C26 C25 127.4(9) . . ? N23 C27 N24 109.2(9) . . ? N23 C27 C28 131.8(10) . . ? N24 C27 C28 119.1(10) . . ? C29 C28 C27 118.5(11) . . ? C28 C29 C30 120.7(11) . . ? C31 C30 C29 121.4(11) . . ? C30 C31 N24 118.0(11) . . ? O2 Cl1 O4 112.6(11) . . ? O2 Cl1 O1 109.7(9) . . ? O4 Cl1 O1 108.6(8) . . ? O2 Cl1 O3 109.0(10) . . ? O4 Cl1 O3 107.0(12) . . ? O1 Cl1 O3 109.9(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Co1 N1 C1 -11.5(9) 2_666 . . . ? N2 Co1 N1 C1 168.5(9) . . . . ? N23 Co1 N1 C1 72.7(9) . . . . ? N23 Co1 N1 C1 -107.3(9) 2_666 . . . ? N2 Co1 N1 C5 174.4(7) 2_666 . . . ? N2 Co1 N1 C5 -5.6(7) . . . . ? N23 Co1 N1 C5 -101.4(8) . . . . ? N23 Co1 N1 C5 78.6(8) 2_666 . . . ? N1 Co1 N2 C6 -168.2(7) 2_666 . . . ? N1 Co1 N2 C6 11.8(7) . . . . ? N23 Co1 N2 C6 99.9(8) . . . . ? N23 Co1 N2 C6 -80.1(8) 2_666 . . . ? N1 Co1 N2 N3 -14.2(10) 2_666 . . . ? N1 Co1 N2 N3 165.8(10) . . . . ? N23 Co1 N2 N3 -106.1(9) . . . . ? N23 Co1 N2 N3 73.9(9) 2_666 . . . ? C6 N2 N3 C7 -1.7(11) . . . . ? Co1 N2 N3 C7 -156.5(8) . . . . ? C5 N1 C1 C2 -1.7(16) . . . . ? Co1 N1 C1 C2 -175.7(8) . . . . ? N1 C1 C2 C3 0.7(18) . . . . ? C1 C2 C3 C4 -0.3(19) . . . . ? C2 C3 C4 C5 0.8(18) . . . . ? C1 N1 C5 C4 2.3(16) . . . . ? Co1 N1 C5 C4 176.7(8) . . . . ? C1 N1 C5 C6 -175.3(9) . . . . ? Co1 N1 C5 C6 -0.9(11) . . . . ? C3 C4 C5 N1 -1.9(17) . . . . ? C3 C4 C5 C6 175.3(11) . . . . ? N3 N2 C6 N4 1.6(12) . . . . ? Co1 N2 C6 N4 161.3(6) . . . . ? N3 N2 C6 C5 -176.6(9) . . . . ? Co1 N2 C6 C5 -16.9(12) . . . . ? C11 N4 C6 N2 -178.1(11) . . . . ? C7 N4 C6 N2 -0.9(11) . . . . ? C11 N4 C6 C5 0(2) . . . . ? C7 N4 C6 C5 177.0(11) . . . . ? N1 C5 C6 N2 11.9(14) . . . . ? C4 C5 C6 N2 -165.6(10) . . . . ? N1 C5 C6 N4 -165.9(10) . . . . ? C4 C5 C6 N4 16.6(18) . . . . ? N2 N3 C7 N4 1.1(11) . . . . ? N2 N3 C7 C8 -177.8(11) . . . . ? C6 N4 C7 N3 -0.1(11) . . . . ? C11 N4 C7 N3 177.5(10) . . . . ? C6 N4 C7 C8 178.8(10) . . . . ? C11 N4 C7 C8 -3.5(15) . . . . ? N3 C7 C8 C9 -180.0(11) . . . . ? N4 C7 C8 C9 1.3(16) . . . . ? C7 C8 C9 C10 1.5(18) . . . . ? C8 C9 C10 C11 -2.1(19) . . . . ? C9 C10 C11 N4 -0.1(18) . . . . ? C6 N4 C11 C10 179.7(11) . . . . ? C7 N4 C11 C10 2.9(16) . . . . ? C26 N22 N23 C27 1.1(13) . . . . ? C26 N22 N23 Co1 174.1(7) . . . . ? N2 Co1 N23 C27 141.9(11) 2_666 . . . ? N2 Co1 N23 C27 -38.1(11) . . . . ? N1 Co1 N23 C27 -141.7(10) 2_666 . . . ? N1 Co1 N23 C27 38.3(11) . . . . ? N2 Co1 N23 N22 -28.6(8) 2_666 . . . ? N2 Co1 N23 N22 151.4(8) . . . . ? N1 Co1 N23 N22 47.7(8) 2_666 . . . ? N1 Co1 N23 N22 -132.3(8) . . . . ? C25 N21 C21 C22 -2(2) . . . . ? N21 C21 C22 C23 0(2) . . . . ? C21 C22 C23 C24 1(2) . . . . ? C22 C23 C24 C25 0(2) . . . . ? C21 N21 C25 C24 2.9(19) . . . . ? C21 N21 C25 C26 -178.1(11) . . . . ? C23 C24 C25 N21 -2(2) . . . . ? C23 C24 C25 C26 178.8(12) . . . . ? N23 N22 C26 N24 -0.9(13) . . . . ? N23 N22 C26 C25 -179.1(10) . . . . ? C31 N24 C26 N22 -178.8(12) . . . . ? C27 N24 C26 N22 0.4(12) . . . . ? C31 N24 C26 C25 -1(2) . . . . ? C27 N24 C26 C25 178.4(11) . . . . ? N21 C25 C26 N22 178.6(11) . . . . ? C24 C25 C26 N22 -2.4(18) . . . . ? N21 C25 C26 N24 0.8(18) . . . . ? C24 C25 C26 N24 179.8(11) . . . . ? N22 N23 C27 N24 -0.9(12) . . . . ? Co1 N23 C27 N24 -172.1(7) . . . . ? N22 N23 C27 C28 179.6(13) . . . . ? Co1 N23 C27 C28 8(2) . . . . ? C31 N24 C27 N23 179.6(10) . . . . ? C26 N24 C27 N23 0.4(12) . . . . ? C31 N24 C27 C28 -0.8(17) . . . . ? C26 N24 C27 C28 179.9(11) . . . . ? N23 C27 C28 C29 179.5(12) . . . . ? N24 C27 C28 C29 0.1(18) . . . . ? C27 C28 C29 C30 0(2) . . . . ? C28 C29 C30 C31 0(2) . . . . ? C29 C30 C31 N24 -1(2) . . . . ? C26 N24 C31 C30 -179.6(12) . . . . ? C27 N24 C31 C30 1.4(17) . . . . ? _diffrn_measured_fraction_theta_max 0.732 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.732 _refine_diff_density_max 0.869 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.107 # Attachment 'CCDC_755116_revised.cif' data_jmk_afp8_2 _database_code_depnum_ccdc_archive 'CCDC 755116' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C26 H16 Fe N14 ; _chemical_formula_sum 'C26 H16 Fe N14' _chemical_formula_weight 580.38 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' 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 I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 16.191(2) _cell_length_b 7.3503(8) _cell_length_c 21.399(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.349(7) _cell_angle_gamma 90.00 _cell_volume 2519.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 2152 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 24.70 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.647 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7820 _exptl_absorpt_correction_T_max 0.9684 _exptl_absorpt_process_details ? _exptl_special_details ; March 2001 T Higashi ; _diffrn_ambient_temperature 113(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 'Rigaku R-Axis SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12565 _diffrn_reflns_av_R_equivalents 0.0872 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 24.70 _reflns_number_total 2152 _reflns_number_gt 1539 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0311P)^2^+1.4000P] 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 2152 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Fe1 Fe 0.5000 0.0000 0.5000 0.01881(18) Uani 1 2 d S . . N1 N 0.50959(14) -0.0020(4) 0.81055(10) 0.0254(5) Uani 1 1 d . . . N2 N 0.53740(13) 0.0239(3) 0.64797(10) 0.0213(5) Uani 1 1 d . . . N3 N 0.47473(13) 0.0182(3) 0.59721(10) 0.0213(5) Uani 1 1 d . . . N4 N 0.41729(13) 0.0570(3) 0.68399(10) 0.0199(5) Uani 1 1 d . . . N20 N 0.39814(15) -0.1887(3) 0.47637(11) 0.0242(6) Uani 1 1 d . . . N21 N 0.34566(15) -0.4887(3) 0.43951(13) 0.0368(7) Uani 1 1 d . . . N22 N 0.41900(15) -0.7720(3) 0.47554(11) 0.0241(6) Uani 1 1 d . . . C1 C 0.55465(18) -0.0070(4) 0.86845(13) 0.0298(7) Uani 1 1 d . . . H1 H 0.5277 -0.0461 0.9027 0.036 Uiso 1 1 calc R . . C2 C 0.63761(19) 0.0413(4) 0.88100(13) 0.0281(7) Uani 1 1 d . . . H2 H 0.6674 0.0306 0.9225 0.034 Uiso 1 1 calc R . . C3 C 0.67664(18) 0.1057(4) 0.83213(13) 0.0272(7) Uani 1 1 d . . . H3 H 0.7336 0.1413 0.8395 0.033 Uiso 1 1 calc R . . C4 C 0.63145(18) 0.1173(4) 0.77224(13) 0.0243(7) Uani 1 1 d . . . H4 H 0.6561 0.1654 0.7381 0.029 Uiso 1 1 calc R . . C5 C 0.54926(17) 0.0572(3) 0.76310(12) 0.0203(6) Uani 1 1 d . . . C6 C 0.50290(17) 0.0485(3) 0.69931(13) 0.0212(6) Uani 1 1 d . . . C7 C 0.40220(17) 0.0370(3) 0.61898(12) 0.0208(6) Uani 1 1 d . . . C8 C 0.31919(18) 0.0391(3) 0.58754(13) 0.0249(7) Uani 1 1 d . . . H8 H 0.3075 0.0228 0.5431 0.030 Uiso 1 1 calc R . . C9 C 0.25673(18) 0.0650(4) 0.62248(14) 0.0267(7) Uani 1 1 d . . . H9 H 0.2004 0.0644 0.6025 0.032 Uiso 1 1 calc R . . C10 C 0.27492(18) 0.0932(4) 0.68912(14) 0.0257(7) Uani 1 1 d . . . H10 H 0.2304 0.1167 0.7124 0.031 Uiso 1 1 calc R . . C11 C 0.35351(17) 0.0873(4) 0.71963(13) 0.0235(7) Uani 1 1 d . . . H11 H 0.3650 0.1033 0.7641 0.028 Uiso 1 1 calc R . . C21 C 0.38702(18) -0.6362(4) 0.46021(13) 0.0223(7) Uani 1 1 d . . . C20 C 0.37612(17) -0.3329(4) 0.46023(13) 0.0210(7) 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 0.0229(3) 0.0165(3) 0.0163(3) -0.0005(2) 0.0000(2) 0.0004(3) N1 0.0255(13) 0.0320(13) 0.0183(12) -0.0005(11) 0.0014(10) 0.0023(12) N2 0.0207(12) 0.0258(13) 0.0170(12) 0.0000(10) 0.0015(10) 0.0015(11) N3 0.0211(12) 0.0246(12) 0.0174(12) 0.0005(10) -0.0001(10) 0.0009(11) N4 0.0176(12) 0.0231(12) 0.0189(13) 0.0004(9) 0.0020(10) 0.0008(10) N20 0.0254(14) 0.0217(13) 0.0243(14) 0.0013(11) 0.0004(11) 0.0015(11) N21 0.0334(14) 0.0169(13) 0.0521(17) -0.0026(13) -0.0211(12) 0.0008(13) N22 0.0271(14) 0.0210(13) 0.0225(14) -0.0017(10) -0.0023(11) 0.0020(12) C1 0.0370(18) 0.0333(16) 0.0191(15) 0.0005(14) 0.0037(13) 0.0033(16) C2 0.0343(18) 0.0324(17) 0.0161(15) -0.0042(12) -0.0016(13) 0.0064(14) C3 0.0246(16) 0.0296(16) 0.0250(17) -0.0054(13) -0.0039(14) 0.0033(14) C4 0.0245(16) 0.0245(15) 0.0235(16) 0.0020(12) 0.0020(13) 0.0002(13) C5 0.0228(15) 0.0195(14) 0.0182(15) -0.0035(11) 0.0015(12) 0.0016(11) C6 0.0203(15) 0.0217(15) 0.0213(15) 0.0012(11) 0.0023(12) 0.0021(11) C7 0.0242(15) 0.0221(16) 0.0160(14) -0.0005(11) 0.0033(12) -0.0006(12) C8 0.0276(16) 0.0235(16) 0.0214(15) -0.0002(12) -0.0030(13) 0.0003(13) C9 0.0208(16) 0.0221(15) 0.0357(18) 0.0000(13) -0.0014(14) -0.0001(12) C10 0.0231(16) 0.0249(15) 0.0297(17) -0.0001(13) 0.0058(13) 0.0028(13) C11 0.0280(17) 0.0217(14) 0.0226(16) -0.0003(12) 0.0091(14) 0.0001(13) C21 0.0203(16) 0.0239(16) 0.0212(16) -0.0034(13) -0.0025(13) -0.0051(13) C20 0.0182(16) 0.0224(17) 0.0205(16) 0.0032(12) -0.0034(13) 0.0032(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 Fe1 N22 2.146(2) 1_565 ? Fe1 N22 2.146(2) 5_646 ? Fe1 N20 2.158(2) 5_656 ? Fe1 N20 2.158(2) . ? Fe1 N3 2.181(2) . ? Fe1 N3 2.182(2) 5_656 ? N1 C1 1.344(3) . ? N1 C5 1.350(3) . ? N2 C6 1.315(3) . ? N2 N3 1.375(3) . ? N3 C7 1.332(3) . ? N4 C6 1.379(3) . ? N4 C7 1.385(3) . ? N4 C11 1.388(3) . ? N20 C20 1.155(3) . ? N21 C20 1.300(4) . ? N21 C21 1.317(4) . ? N22 C21 1.150(3) . ? N22 Fe1 2.146(2) 1_545 ? C1 C2 1.378(4) . ? C1 H1 0.9500 . ? C2 C3 1.381(4) . ? C2 H2 0.9500 . ? C3 C4 1.383(4) . ? C3 H3 0.9500 . ? C4 C5 1.389(4) . ? C4 H4 0.9500 . ? C5 C6 1.461(4) . ? C7 C8 1.413(4) . ? C8 C9 1.356(4) . ? C8 H8 0.9500 . ? C9 C10 1.429(4) . ? C9 H9 0.9500 . ? C10 C11 1.344(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? 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 N22 Fe1 N22 180.00(7) 1_565 5_646 ? N22 Fe1 N20 88.53(9) 1_565 5_656 ? N22 Fe1 N20 91.47(9) 5_646 5_656 ? N22 Fe1 N20 91.47(9) 1_565 . ? N22 Fe1 N20 88.53(9) 5_646 . ? N20 Fe1 N20 180.00(13) 5_656 . ? N22 Fe1 N3 89.55(9) 1_565 . ? N22 Fe1 N3 90.45(9) 5_646 . ? N20 Fe1 N3 88.85(9) 5_656 . ? N20 Fe1 N3 91.15(9) . . ? N22 Fe1 N3 90.45(9) 1_565 5_656 ? N22 Fe1 N3 89.55(9) 5_646 5_656 ? N20 Fe1 N3 91.15(9) 5_656 5_656 ? N20 Fe1 N3 88.85(9) . 5_656 ? N3 Fe1 N3 179.999(1) . 5_656 ? C1 N1 C5 116.6(2) . . ? C6 N2 N3 108.1(2) . . ? C7 N3 N2 107.9(2) . . ? C7 N3 Fe1 129.55(17) . . ? N2 N3 Fe1 122.42(16) . . ? C6 N4 C7 105.0(2) . . ? C6 N4 C11 132.8(2) . . ? C7 N4 C11 122.2(2) . . ? C20 N20 Fe1 148.4(2) . . ? C20 N21 C21 117.5(2) . . ? C21 N22 Fe1 169.0(2) . 1_545 ? N1 C1 C2 123.8(3) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C1 C2 C3 118.8(3) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C2 C3 C4 118.9(3) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 118.6(3) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? N1 C5 C4 123.2(3) . . ? N1 C5 C6 116.9(2) . . ? C4 C5 C6 119.8(3) . . ? N2 C6 N4 110.0(2) . . ? N2 C6 C5 124.3(2) . . ? N4 C6 C5 125.6(2) . . ? N3 C7 N4 109.1(2) . . ? N3 C7 C8 131.3(2) . . ? N4 C7 C8 119.6(2) . . ? C9 C8 C7 118.2(3) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C8 C9 C10 120.6(3) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 121.6(3) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C10 C11 N4 117.8(3) . . ? C10 C11 H11 121.1 . . ? N4 C11 H11 121.1 . . ? N22 C21 N21 175.1(3) . . ? N20 C20 N21 175.1(3) . . ? 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 C6 N2 N3 C7 -0.9(3) . . . . ? C6 N2 N3 Fe1 175.33(17) . . . . ? N22 Fe1 N3 C7 46.6(2) 1_565 . . . ? N22 Fe1 N3 C7 -133.4(2) 5_646 . . . ? N20 Fe1 N3 C7 135.2(2) 5_656 . . . ? N20 Fe1 N3 C7 -44.8(2) . . . . ? N22 Fe1 N3 N2 -128.7(2) 1_565 . . . ? N22 Fe1 N3 N2 51.3(2) 5_646 . . . ? N20 Fe1 N3 N2 -40.14(19) 5_656 . . . ? N20 Fe1 N3 N2 139.86(19) . . . . ? N22 Fe1 N20 C20 154.1(5) 1_565 . . . ? N22 Fe1 N20 C20 -25.9(5) 5_646 . . . ? N3 Fe1 N20 C20 -116.3(4) . . . . ? N3 Fe1 N20 C20 63.7(4) 5_656 . . . ? C5 N1 C1 C2 -1.2(5) . . . . ? N1 C1 C2 C3 2.7(5) . . . . ? C1 C2 C3 C4 -0.8(4) . . . . ? C2 C3 C4 C5 -2.4(4) . . . . ? C1 N1 C5 C4 -2.3(4) . . . . ? C1 N1 C5 C6 175.0(3) . . . . ? C3 C4 C5 N1 4.1(4) . . . . ? C3 C4 C5 C6 -173.1(2) . . . . ? N3 N2 C6 N4 0.8(3) . . . . ? N3 N2 C6 C5 178.4(2) . . . . ? C7 N4 C6 N2 -0.4(3) . . . . ? C11 N4 C6 N2 -177.2(3) . . . . ? C7 N4 C6 C5 -178.0(2) . . . . ? C11 N4 C6 C5 5.2(5) . . . . ? N1 C5 C6 N2 -149.6(3) . . . . ? C4 C5 C6 N2 27.8(4) . . . . ? N1 C5 C6 N4 27.6(4) . . . . ? C4 C5 C6 N4 -155.0(3) . . . . ? N2 N3 C7 N4 0.6(3) . . . . ? Fe1 N3 C7 N4 -175.23(17) . . . . ? N2 N3 C7 C8 -179.4(3) . . . . ? Fe1 N3 C7 C8 4.8(4) . . . . ? C6 N4 C7 N3 -0.1(3) . . . . ? C11 N4 C7 N3 177.1(2) . . . . ? C6 N4 C7 C8 179.9(2) . . . . ? C11 N4 C7 C8 -2.9(4) . . . . ? N3 C7 C8 C9 -178.6(3) . . . . ? N4 C7 C8 C9 1.5(4) . . . . ? C7 C8 C9 C10 1.3(4) . . . . ? C8 C9 C10 C11 -2.9(4) . . . . ? C9 C10 C11 N4 1.5(4) . . . . ? C6 N4 C11 C10 177.7(3) . . . . ? C7 N4 C11 C10 1.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.70 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.263 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.068 data_jmk_afp_09 _database_code_depnum_ccdc_archive 'CCDC 755117' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C11 H11 N5 ; _chemical_formula_sum 'C11 H11 N5' _chemical_formula_weight 213.25 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(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 12.178(2) _cell_length_b 12.462(3) _cell_length_c 14.973(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.15(3) _cell_angle_gamma 90.00 _cell_volume 2089.4(7) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5076 _cell_measurement_theta_min 1.82 _cell_measurement_theta_max 28.14 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type 'semi-empirical (SADABS)' _exptl_absorpt_correction_T_min 0.9562 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details ; March 2001 T Higashi ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 46697 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.14 _reflns_number_total 5076 _reflns_number_gt 3386 _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^)+(0.0482P)^2^+0.3951P] 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 5076 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 N1 N 0.38533(10) 0.33847(10) -0.05182(9) 0.0376(3) Uani 1 1 d . . . N2 N 0.55662(11) 0.39495(10) 0.07700(9) 0.0318(3) Uani 1 1 d . . . H2A H 0.6325(15) 0.4078(13) 0.0966(11) 0.038(4) Uiso 1 1 d . . . N3 N 0.48916(10) 0.43512(9) 0.12463(9) 0.0316(3) Uani 1 1 d . . . N4 N 0.67189(11) 0.47843(12) 0.25487(11) 0.0418(3) Uani 1 1 d . . . H4A H 0.7195(17) 0.4745(16) 0.2174(14) 0.064(6) Uiso 1 1 d . . . H4B H 0.6985(16) 0.5196(15) 0.3098(14) 0.057(6) Uiso 1 1 d . . . N5 N 0.55139(12) 0.55596(11) 0.35350(10) 0.0439(3) Uani 1 1 d . . . C1 C 0.33902(14) 0.28507(14) -0.13670(13) 0.0479(4) Uani 1 1 d . . . H1 H 0.2545 0.2792 -0.1670 0.057 Uiso 1 1 calc R . . C2 C 0.40379(16) 0.23896(13) -0.18227(12) 0.0476(4) Uani 1 1 d . . . H2 H 0.3660 0.2004 -0.2412 0.057 Uiso 1 1 calc R . . C3 C 0.52696(15) 0.24995(12) -0.13993(12) 0.0410(4) Uani 1 1 d . . . H3 H 0.5754 0.2197 -0.1701 0.049 Uiso 1 1 calc R . . C4 C 0.57778(13) 0.30451(12) -0.05475(11) 0.0342(3) Uani 1 1 d . . . H4 H 0.6619 0.3140 -0.0252 0.041 Uiso 1 1 calc R . . C5 C 0.50393(12) 0.34647(11) -0.01135(10) 0.0293(3) Uani 1 1 d . . . C6 C 0.55020(12) 0.47632(11) 0.20914(11) 0.0316(3) Uani 1 1 d . . . C7 C 0.48355(13) 0.52158(11) 0.26427(11) 0.0336(3) Uani 1 1 d . . . C8 C 0.36030(14) 0.52853(13) 0.22538(13) 0.0411(4) Uani 1 1 d . . . H8 H 0.3147 0.5036 0.1615 0.049 Uiso 1 1 calc R . . C9 C 0.30528(15) 0.57242(14) 0.28145(14) 0.0514(5) Uani 1 1 d . . . H9 H 0.2208 0.5791 0.2565 0.062 Uiso 1 1 calc R . . C10 C 0.37391(16) 0.60636(16) 0.37386(15) 0.0564(5) Uani 1 1 d . . . H10 H 0.3377 0.6355 0.4143 0.068 Uiso 1 1 calc R . . C11 C 0.49517(16) 0.59755(15) 0.40666(14) 0.0528(5) Uani 1 1 d . . . H11 H 0.5422 0.6221 0.4704 0.063 Uiso 1 1 calc R . . N11 N 0.82276(10) 0.41902(9) 0.14132(9) 0.0331(3) Uani 1 1 d . . . N12 N 0.84251(11) 0.56494(10) 0.05513(9) 0.0352(3) Uani 1 1 d . . . H12A H 0.7692(15) 0.5805(13) 0.0452(12) 0.045(5) Uiso 1 1 d . . . N13 N 0.91853(10) 0.64154(9) 0.04367(9) 0.0326(3) Uani 1 1 d . . . N14 N 0.75179(13) 0.73266(14) -0.06934(12) 0.0517(4) Uani 1 1 d . . . H14A H 0.6982(17) 0.6994(16) -0.0557(14) 0.060(6) Uiso 1 1 d . . . H14B H 0.7326(15) 0.7958(16) -0.1004(14) 0.054(5) Uiso 1 1 d . . . N15 N 0.90057(11) 0.87159(10) -0.09965(9) 0.0374(3) Uani 1 1 d . . . C21 C 0.87191(14) 0.33449(12) 0.19923(11) 0.0365(3) Uani 1 1 d . . . H21 H 0.8209 0.2904 0.2179 0.044 Uiso 1 1 calc R . . C22 C 0.98953(14) 0.30782(12) 0.23291(11) 0.0386(4) Uani 1 1 d . . . H22 H 1.0205 0.2484 0.2752 0.046 Uiso 1 1 calc R . . C23 C 1.06243(13) 0.37098(13) 0.20294(12) 0.0399(4) Uani 1 1 d . . . H23 H 1.1450 0.3547 0.2243 0.048 Uiso 1 1 calc R . . C24 C 1.01612(12) 0.45628(12) 0.14291(11) 0.0340(3) Uani 1 1 d . . . H24 H 1.0653 0.4989 0.1210 0.041 Uiso 1 1 calc R . . C25 C 0.89496(12) 0.47982(11) 0.11418(10) 0.0282(3) Uani 1 1 d . . . C26 C 0.86966(12) 0.71891(12) -0.01542(10) 0.0324(3) Uani 1 1 d . . . C27 C 0.95183(13) 0.79775(12) -0.03093(10) 0.0318(3) Uani 1 1 d . . . C28 C 1.07422(13) 0.79406(13) 0.02255(11) 0.0384(4) Uani 1 1 d . . . H28 H 1.1080 0.7411 0.0714 0.046 Uiso 1 1 calc R . . C29 C 1.14585(14) 0.86839(13) 0.00363(12) 0.0428(4) Uani 1 1 d . . . H29 H 1.2298 0.8679 0.0396 0.051 Uiso 1 1 calc R . . C30 C 1.09408(14) 0.94361(13) -0.06832(12) 0.0426(4) Uani 1 1 d . . . H30 H 1.1415 0.9953 -0.0834 0.051 Uiso 1 1 calc R . . C31 C 0.97260(14) 0.94189(13) -0.11740(12) 0.0415(4) Uani 1 1 d . . . H31 H 0.9373 0.9937 -0.1670 0.050 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 N1 0.0288(6) 0.0374(7) 0.0415(8) -0.0098(6) 0.0084(6) -0.0025(5) N2 0.0247(6) 0.0378(7) 0.0332(7) -0.0064(5) 0.0116(5) -0.0009(5) N3 0.0303(6) 0.0313(6) 0.0358(7) -0.0030(5) 0.0160(5) 0.0005(5) N4 0.0307(7) 0.0550(9) 0.0386(8) -0.0127(7) 0.0126(6) -0.0015(6) N5 0.0448(8) 0.0485(8) 0.0420(8) -0.0115(6) 0.0210(7) -0.0047(6) C1 0.0344(8) 0.0471(10) 0.0489(10) -0.0139(8) 0.0021(7) -0.0011(7) C2 0.0529(10) 0.0407(9) 0.0381(9) -0.0127(7) 0.0060(8) 0.0026(8) C3 0.0500(10) 0.0359(8) 0.0377(9) -0.0026(7) 0.0181(8) 0.0068(7) C4 0.0339(8) 0.0331(8) 0.0352(8) -0.0004(6) 0.0133(6) 0.0035(6) C5 0.0309(7) 0.0241(7) 0.0307(7) 0.0006(6) 0.0097(6) 0.0006(5) C6 0.0319(7) 0.0298(7) 0.0339(8) -0.0011(6) 0.0139(6) -0.0018(6) C7 0.0381(8) 0.0275(7) 0.0388(9) -0.0028(6) 0.0189(7) -0.0035(6) C8 0.0393(8) 0.0385(9) 0.0491(10) -0.0104(7) 0.0214(7) -0.0061(7) C9 0.0399(9) 0.0509(10) 0.0719(13) -0.0192(9) 0.0312(9) -0.0092(8) C10 0.0549(11) 0.0606(12) 0.0691(13) -0.0277(10) 0.0410(10) -0.0139(9) C11 0.0545(11) 0.0596(11) 0.0508(11) -0.0214(9) 0.0277(9) -0.0113(9) N11 0.0305(6) 0.0326(6) 0.0356(7) 0.0006(5) 0.0125(5) 0.0001(5) N12 0.0268(6) 0.0374(7) 0.0407(8) 0.0102(6) 0.0125(6) 0.0045(5) N13 0.0328(6) 0.0315(6) 0.0338(7) 0.0030(5) 0.0134(5) 0.0008(5) N14 0.0339(8) 0.0582(10) 0.0568(10) 0.0288(8) 0.0113(7) 0.0029(7) N15 0.0399(7) 0.0370(7) 0.0355(7) 0.0074(6) 0.0150(6) 0.0049(6) C21 0.0417(8) 0.0314(8) 0.0390(9) 0.0012(6) 0.0186(7) -0.0028(6) C22 0.0431(9) 0.0325(8) 0.0386(9) 0.0061(7) 0.0144(7) 0.0070(7) C23 0.0305(7) 0.0432(9) 0.0436(9) 0.0051(7) 0.0119(7) 0.0084(7) C24 0.0306(7) 0.0357(8) 0.0371(8) 0.0028(6) 0.0146(6) 0.0015(6) C25 0.0287(7) 0.0294(7) 0.0257(7) -0.0017(6) 0.0098(6) 0.0007(6) C26 0.0316(7) 0.0372(8) 0.0282(7) 0.0015(6) 0.0115(6) 0.0038(6) C27 0.0359(8) 0.0313(7) 0.0292(8) 0.0005(6) 0.0139(6) 0.0031(6) C28 0.0390(8) 0.0396(8) 0.0357(8) 0.0039(7) 0.0135(7) 0.0034(7) C29 0.0355(8) 0.0451(9) 0.0469(10) 0.0006(8) 0.0152(7) 0.0012(7) C30 0.0453(9) 0.0383(9) 0.0501(10) 0.0023(7) 0.0252(8) -0.0030(7) C31 0.0462(9) 0.0381(8) 0.0428(9) 0.0104(7) 0.0203(8) 0.0044(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 N1 C5 1.3323(18) . ? N1 C1 1.346(2) . ? N2 C5 1.3635(18) . ? N2 N3 1.3766(16) . ? N3 C6 1.2952(18) . ? N4 C6 1.3667(19) . ? N5 C7 1.335(2) . ? N5 C11 1.341(2) . ? C1 C2 1.357(2) . ? C2 C3 1.387(2) . ? C3 C4 1.361(2) . ? C4 C5 1.402(2) . ? C6 C7 1.478(2) . ? C7 C8 1.383(2) . ? C8 C9 1.377(2) . ? C9 C10 1.372(3) . ? C10 C11 1.365(2) . ? N11 C25 1.3391(18) . ? N11 C21 1.3460(19) . ? N12 C25 1.3677(18) . ? N12 N13 1.3867(17) . ? N13 C26 1.2856(18) . ? N14 C26 1.353(2) . ? N15 C27 1.3379(19) . ? N15 C31 1.338(2) . ? C21 C22 1.360(2) . ? C22 C23 1.387(2) . ? C23 C24 1.363(2) . ? C24 C25 1.3961(19) . ? C26 C27 1.484(2) . ? C27 C28 1.388(2) . ? C28 C29 1.376(2) . ? C29 C30 1.379(2) . ? C30 C31 1.369(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 116.31(14) . . ? C5 N2 N3 120.97(12) . . ? C6 N3 N2 114.84(12) . . ? C7 N5 C11 117.28(14) . . ? N1 C1 C2 125.00(15) . . ? C1 C2 C3 117.81(15) . . ? C4 C3 C2 119.30(15) . . ? C3 C4 C5 118.87(14) . . ? N1 C5 N2 119.14(13) . . ? N1 C5 C4 122.66(13) . . ? N2 C5 C4 118.18(13) . . ? N3 C6 N4 126.15(14) . . ? N3 C6 C7 117.81(13) . . ? N4 C6 C7 115.98(13) . . ? N5 C7 C8 122.91(14) . . ? N5 C7 C6 114.94(13) . . ? C8 C7 C6 122.14(14) . . ? C9 C8 C7 118.42(16) . . ? C10 C9 C8 119.20(16) . . ? C11 C10 C9 118.81(16) . . ? N5 C11 C10 123.36(17) . . ? C25 N11 C21 117.36(12) . . ? C25 N12 N13 116.69(12) . . ? C26 N13 N12 116.78(12) . . ? C27 N15 C31 117.32(13) . . ? N11 C21 C22 124.55(14) . . ? C21 C22 C23 117.16(14) . . ? C24 C23 C22 120.31(14) . . ? C23 C24 C25 118.70(14) . . ? N11 C25 N12 116.07(12) . . ? N11 C25 C24 121.87(13) . . ? N12 C25 C24 122.04(13) . . ? N13 C26 N14 126.96(14) . . ? N13 C26 C27 116.48(13) . . ? N14 C26 C27 116.43(13) . . ? N15 C27 C28 122.48(14) . . ? N15 C27 C26 115.86(13) . . ? C28 C27 C26 121.66(13) . . ? C29 C28 C27 118.87(15) . . ? C28 C29 C30 119.09(15) . . ? C31 C30 C29 118.31(15) . . ? N15 C31 C30 123.92(15) . . ? 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 C5 N2 N3 C6 178.06(13) . . . . ? C5 N1 C1 C2 0.7(3) . . . . ? N1 C1 C2 C3 -1.9(3) . . . . ? C1 C2 C3 C4 0.9(2) . . . . ? C2 C3 C4 C5 1.1(2) . . . . ? C1 N1 C5 N2 -176.78(14) . . . . ? C1 N1 C5 C4 1.5(2) . . . . ? N3 N2 C5 N1 0.2(2) . . . . ? N3 N2 C5 C4 -178.19(12) . . . . ? C3 C4 C5 N1 -2.4(2) . . . . ? C3 C4 C5 N2 175.89(14) . . . . ? N2 N3 C6 N4 -3.1(2) . . . . ? N2 N3 C6 C7 179.67(12) . . . . ? C11 N5 C7 C8 0.8(2) . . . . ? C11 N5 C7 C6 -179.85(14) . . . . ? N3 C6 C7 N5 175.51(13) . . . . ? N4 C6 C7 N5 -2.0(2) . . . . ? N3 C6 C7 C8 -5.2(2) . . . . ? N4 C6 C7 C8 177.37(14) . . . . ? N5 C7 C8 C9 -0.3(2) . . . . ? C6 C7 C8 C9 -179.59(15) . . . . ? C7 C8 C9 C10 -0.8(3) . . . . ? C8 C9 C10 C11 1.4(3) . . . . ? C7 N5 C11 C10 -0.2(3) . . . . ? C9 C10 C11 N5 -0.9(3) . . . . ? C25 N12 N13 C26 176.77(13) . . . . ? C25 N11 C21 C22 1.0(2) . . . . ? N11 C21 C22 C23 -1.8(2) . . . . ? C21 C22 C23 C24 0.5(2) . . . . ? C22 C23 C24 C25 1.4(2) . . . . ? C21 N11 C25 N12 179.81(13) . . . . ? C21 N11 C25 C24 1.1(2) . . . . ? N13 N12 C25 N11 166.28(12) . . . . ? N13 N12 C25 C24 -15.0(2) . . . . ? C23 C24 C25 N11 -2.2(2) . . . . ? C23 C24 C25 N12 179.11(14) . . . . ? N12 N13 C26 N14 -1.4(2) . . . . ? N12 N13 C26 C27 -177.15(12) . . . . ? C31 N15 C27 C28 1.6(2) . . . . ? C31 N15 C27 C26 -178.07(14) . . . . ? N13 C26 C27 N15 173.59(13) . . . . ? N14 C26 C27 N15 -2.6(2) . . . . ? N13 C26 C27 C28 -6.1(2) . . . . ? N14 C26 C27 C28 177.74(15) . . . . ? N15 C27 C28 C29 -0.7(2) . . . . ? C26 C27 C28 C29 178.97(14) . . . . ? C27 C28 C29 C30 -0.5(2) . . . . ? C28 C29 C30 C31 0.8(2) . . . . ? C27 N15 C31 C30 -1.4(2) . . . . ? C29 C30 C31 N15 0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.14 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.186 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.037