# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 186/1380 data_global _publ_contact_author ; Dra. Miren Karmele Urtiaga Dpto. de Mineralog\'ia y Petrolog\'ia Universidad del Pa\'is Vasco Apartado 644 48080 Bilbao Spain ; _publ_contact_author_phone '34 4 6012555' _publ_contact_author_fax '34 4 4648500' _publ_contact_author_email nppurgrm@lg.ehu.es _publ_requested_journal 'Am. Chem. Soc, Dalton Trans' loop_ _publ_author_name _publ_author_address 'Hern\'andez, M.L.' ; Dpto. Qu\'imica Inorg\'anica Facultad de CIencias Uiversidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Barandika, M.G.' ; Dpto. Qu\'imica Inorg\'anica Facultad de Farmacia Uiversidad del Pa\'is Vasco/E.H.U. P.O. Box 450 01080 Vitoria Spain ; 'Urtiaga, M.K.' ; Dpto. de Mineralog\'ia y Petrolog\'ia Facultad de CIencias Uiversidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Cort\'es, R.' ; Dpto. Qu\'imica Inorg\'anica Facultad de Farmacia Uiversidad del Pa\'is Vasco/E.H.U. P.O. Box 450 01080 Vitoria Spain ; 'Lezama, L.' ; Dpto. Qu\'imica Inorg\'anica Facultad de CIencias Uiversidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Arriortua, M.I.' ; Dpto. de Mineralog\'ia y Petrolog\'ia Facultad de CIencias Uiversidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Rojo, T.' ; Dpto. Qu\'imica Inorg\'anica Facultad de CIencias Uiversidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; data_ic9809270 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H12 Fe0.50 N3 S' _chemical_formula_weight 270.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.077(4) _cell_length_b 9.995(3) _cell_length_c 14.588(4) _cell_angle_alpha 90.00(2) _cell_angle_beta 110.23(3) _cell_angle_gamma 90.00(3) _cell_volume 2610.0(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_colour yelow _exptl_crystal_density_diffrn 1.375 _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.764 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method '\w-2\q' _diffrn_standards_number 2 _diffrn_standards_interval_count 200 _diffrn_standards_decay_% 1 _diffrn_reflns_number 7943 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 31.07 _reflns_number_total 3940 _reflns_number_gt 3168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Enraf-Nonius CAD-4' _computing_cell_refinement 'Enraf-Nonius CAD-4' _computing_data_reduction 'Xtal 3.2 (Hall, Flack & Stewart, 1992)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0490P)^2^+1.2833P] 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_number_reflns 3940 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.003 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 Fe Fe 0.0000 0.00426(3) 0.2500 0.03697(10) Uani 1 2 d S . . N3 N 0.07840(9) -0.00325(15) 0.18139(13) 0.0501(4) Uani 1 1 d . . . C13 C 0.13370(9) -0.03527(16) 0.17821(11) 0.0383(3) Uani 1 1 d . . . S S 0.21114(3) -0.08092(7) 0.17501(4) 0.06385(16) Uani 1 1 d . . . N1 N -0.06659(8) -0.15304(14) 0.15006(10) 0.0423(3) Uani 1 1 d . . . C1 C -0.08765(10) -0.14204(18) 0.05326(13) 0.0469(4) Uani 1 1 d . . . C2 C -0.13473(10) -0.22942(19) -0.00989(13) 0.0470(4) Uani 1 1 d . . . C3 C -0.16274(8) -0.33669(16) 0.02561(12) 0.0399(3) Uani 1 1 d . . . C4 C -0.14115(10) -0.34783(18) 0.12595(14) 0.0471(4) Uani 1 1 d . . . C5 C -0.09393(11) -0.25618(18) 0.18473(13) 0.0475(4) Uani 1 1 d . . . C6 C -0.21297(10) -0.43530(18) -0.04189(14) 0.0474(4) Uani 1 1 d . . . C7 C -0.17176(11) -0.5469(2) -0.07291(14) 0.0496(4) Uani 1 1 d . . . C8 C -0.12472(9) -0.7954(2) 0.13511(15) 0.0495(4) Uani 1 1 d . . . C9 C -0.16143(10) -0.7011(2) 0.06855(15) 0.0522(4) Uani 1 1 d . . . C10 C -0.13085(9) -0.64128(16) 0.00706(12) 0.0418(3) Uani 1 1 d . . . C11 C -0.06126(11) -0.6792(2) 0.02009(18) 0.0600(5) Uani 1 1 d . . . C12 C -0.02726(11) -0.7735(2) 0.08937(18) 0.0620(6) Uani 1 1 d . . . N2 N -0.05750(7) -0.83391(14) 0.14696(11) 0.0428(3) Uani 1 1 d . . . H1 H -0.0681(13) -0.067(3) 0.0306(17) 0.0622(18) Uiso 1 1 d . . . H2 H -0.1494(12) -0.220(2) -0.0753(17) 0.0622(18) Uiso 1 1 d . . . H4 H -0.1585(12) -0.414(2) 0.1552(17) 0.0622(18) Uiso 1 1 d . . . H5 H -0.0778(12) -0.265(2) 0.2569(17) 0.0622(18) Uiso 1 1 d . . . H61 H -0.2401(13) -0.389(2) -0.0954(17) 0.0622(18) Uiso 1 1 d . . . H62 H -0.2438(14) -0.473(2) -0.0104(19) 0.0622(18) Uiso 1 1 d . . . H71 H -0.1409(14) -0.508(2) -0.1022(19) 0.0622(18) Uiso 1 1 d . . . H72 H -0.2047(13) -0.602(2) -0.1218(17) 0.0622(18) Uiso 1 1 d . . . H8 H -0.1442(12) -0.833(3) 0.1786(17) 0.0622(18) Uiso 1 1 d . . . H9 H -0.2057(13) -0.678(2) 0.0649(16) 0.0622(18) Uiso 1 1 d . . . H11 H -0.0376(13) -0.643(2) -0.0196(17) 0.0622(18) Uiso 1 1 d . . . H12 H 0.0220(13) -0.797(2) 0.1041(17) 0.0622(18) Uiso 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 Fe 0.03558(15) 0.03319(16) 0.04581(18) 0.000 0.01875(12) 0.000 N3 0.0499(8) 0.0496(8) 0.0589(9) 0.0081(7) 0.0291(7) 0.0098(6) C13 0.0435(7) 0.0365(7) 0.0381(7) -0.0009(6) 0.0181(6) 0.0004(6) S 0.0441(2) 0.0815(4) 0.0719(3) -0.0060(3) 0.0276(2) 0.0085(2) N1 0.0464(7) 0.0376(7) 0.0439(7) -0.0018(6) 0.0169(6) -0.0031(5) C1 0.0559(9) 0.0419(8) 0.0474(9) 0.0033(7) 0.0235(8) -0.0033(7) C2 0.0553(9) 0.0457(9) 0.0382(8) 0.0026(7) 0.0139(7) 0.0029(7) C3 0.0370(7) 0.0344(7) 0.0466(8) -0.0014(6) 0.0121(6) 0.0073(6) C4 0.0567(9) 0.0374(8) 0.0482(9) 0.0004(7) 0.0192(8) -0.0068(7) C5 0.0608(10) 0.0401(8) 0.0410(8) 0.0011(7) 0.0167(7) -0.0054(7) C6 0.0419(8) 0.0399(9) 0.0508(9) -0.0030(7) 0.0038(7) 0.0078(6) C7 0.0563(10) 0.0431(8) 0.0429(9) -0.0059(7) 0.0089(8) 0.0094(8) C8 0.0430(8) 0.0527(10) 0.0582(10) 0.0064(8) 0.0243(8) 0.0079(7) C9 0.0402(8) 0.0593(11) 0.0595(10) 0.0053(9) 0.0202(8) 0.0129(8) C10 0.0447(8) 0.0331(7) 0.0440(8) -0.0050(6) 0.0106(6) 0.0053(6) C11 0.0516(10) 0.0573(11) 0.0789(13) 0.0249(10) 0.0327(10) 0.0115(8) C12 0.0423(9) 0.0622(12) 0.0888(15) 0.0295(11) 0.0320(10) 0.0142(8) N2 0.0373(6) 0.0375(7) 0.0551(8) 0.0043(6) 0.0179(6) 0.0032(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 Fe N3 2.0688(15) 2 ? Fe N3 2.0688(15) . ? Fe N1 2.2204(16) 2 ? Fe N1 2.2205(16) . ? Fe N2 2.2223(16) 1_565 ? Fe N2 2.2223(16) 2_565 ? N3 C13 1.118(2) . ? C13 S 1.5623(16) . ? N1 C1 1.332(2) . ? N1 C5 1.331(2) . ? C1 C2 1.359(3) . ? C1 H1 0.95(3) . ? C2 C3 1.377(3) . ? C2 H2 0.90(2) . ? C3 C4 1.381(3) . ? C3 C6 1.485(2) . ? C4 C5 1.361(3) . ? C4 H4 0.91(2) . ? C5 H5 0.99(2) . ? C6 C7 1.521(3) . ? C6 H61 0.90(2) . ? C6 H62 0.94(3) . ? C7 C10 1.493(3) . ? C7 H71 0.92(3) . ? C7 H72 0.95(2) . ? C8 N2 1.292(2) . ? C8 C9 1.361(3) . ? C8 H8 0.92(2) . ? C9 C10 1.365(3) . ? C9 H9 0.86(2) . ? C10 C11 1.330(2) . ? C11 C12 1.370(3) . ? C11 H11 0.92(2) . ? C12 N2 1.318(2) . ? C12 H12 0.92(2) . ? N2 Fe 2.2223(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 N3 Fe N3 175.84(9) 2 . ? N3 Fe N1 90.10(7) 2 2 ? N3 Fe N1 86.95(6) . 2 ? N3 Fe N1 86.95(6) 2 . ? N3 Fe N1 90.10(7) . . ? N1 Fe N1 89.84(8) 2 . ? N3 Fe N2 94.78(7) 2 1_565 ? N3 Fe N2 88.25(6) . 1_565 ? N1 Fe N2 174.86(5) 2 1_565 ? N1 Fe N2 91.99(6) . 1_565 ? N3 Fe N2 88.25(6) 2 2_565 ? N3 Fe N2 94.78(7) . 2_565 ? N1 Fe N2 91.99(6) 2 2_565 ? N1 Fe N2 174.87(5) . 2_565 ? N2 Fe N2 86.59(8) 1_565 2_565 ? C13 N3 Fe 151.69(15) . . ? N3 C13 S 179.29(17) . . ? C1 N1 C5 116.90(15) . . ? C1 N1 Fe 122.13(12) . . ? C5 N1 Fe 120.60(12) . . ? N1 C1 C2 123.50(16) . . ? N1 C1 H1 115.2(14) . . ? C2 C1 H1 121.3(14) . . ? C1 C2 C3 119.82(16) . . ? C1 C2 H2 122.7(15) . . ? C3 C2 H2 117.5(15) . . ? C2 C3 C4 116.69(16) . . ? C2 C3 C6 120.85(16) . . ? C4 C3 C6 122.46(16) . . ? C5 C4 C3 120.23(17) . . ? C5 C4 H4 117.6(15) . . ? C3 C4 H4 122.2(15) . . ? N1 C5 C4 122.86(17) . . ? N1 C5 H5 117.0(14) . . ? C4 C5 H5 120.1(14) . . ? C3 C6 C7 113.73(14) . . ? C3 C6 H61 106.2(15) . . ? C7 C6 H61 108.7(15) . . ? C3 C6 H62 108.1(16) . . ? C7 C6 H62 109.0(15) . . ? H61 C6 H62 111(2) . . ? C10 C7 C6 114.53(16) . . ? C10 C7 H71 112.6(15) . . ? C6 C7 H71 107.7(15) . . ? C10 C7 H72 104.5(14) . . ? C6 C7 H72 112.0(14) . . ? H71 C7 H72 105(2) . . ? N2 C8 C9 122.95(18) . . ? N2 C8 H8 114.0(14) . . ? C9 C8 H8 122.9(14) . . ? C8 C9 C10 122.73(16) . . ? C8 C9 H9 118.8(16) . . ? C10 C9 H9 118.5(16) . . ? C11 C10 C9 114.43(17) . . ? C11 C10 C7 121.20(18) . . ? C9 C10 C7 124.27(16) . . ? C10 C11 C12 119.75(19) . . ? C10 C11 H11 118.8(15) . . ? C12 C11 H11 121.4(15) . . ? N2 C12 C11 125.82(17) . . ? N2 C12 H12 111.9(15) . . ? C11 C12 H12 122.1(15) . . ? C8 N2 C12 114.28(16) . . ? C8 N2 Fe 122.84(13) . 1_545 ? C12 N2 Fe 122.81(12) . 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 N3 Fe N3 C13 -57.6(3) 2 . . . ? N1 Fe N3 C13 -12.6(3) 2 . . . ? N1 Fe N3 C13 -102.5(3) . . . . ? N2 Fe N3 C13 165.6(3) 1_565 . . . ? N2 Fe N3 C13 79.1(3) 2_565 . . . ? Fe N3 C13 S 2(16) . . . . ? N3 Fe N1 C1 129.74(14) 2 . . . ? N3 Fe N1 C1 -53.20(14) . . . . ? N1 Fe N1 C1 -140.15(15) 2 . . . ? N2 Fe N1 C1 35.05(14) 1_565 . . . ? N2 Fe N1 C1 108.9(6) 2_565 . . . ? N3 Fe N1 C5 -43.01(14) 2 . . . ? N3 Fe N1 C5 134.05(14) . . . . ? N1 Fe N1 C5 47.10(12) 2 . . . ? N2 Fe N1 C5 -137.70(14) 1_565 . . . ? N2 Fe N1 C5 -63.8(6) 2_565 . . . ? C5 N1 C1 C2 0.1(3) . . . . ? Fe N1 C1 C2 -172.93(14) . . . . ? N1 C1 C2 C3 -0.5(3) . . . . ? C1 C2 C3 C4 0.7(2) . . . . ? C1 C2 C3 C6 -178.64(16) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C6 C3 C4 C5 178.80(16) . . . . ? C1 N1 C5 C4 0.1(3) . . . . ? Fe N1 C5 C4 173.23(14) . . . . ? C3 C4 C5 N1 0.1(3) . . . . ? C2 C3 C6 C7 86.0(2) . . . . ? C4 C3 C6 C7 -93.3(2) . . . . ? C3 C6 C7 C10 68.2(2) . . . . ? N2 C8 C9 C10 1.5(3) . . . . ? C8 C9 C10 C11 -2.4(3) . . . . ? C8 C9 C10 C7 174.14(19) . . . . ? C6 C7 C10 C11 -134.5(2) . . . . ? C6 C7 C10 C9 49.3(3) . . . . ? C9 C10 C11 C12 1.5(3) . . . . ? C7 C10 C11 C12 -175.1(2) . . . . ? C10 C11 C12 N2 0.3(4) . . . . ? C9 C8 N2 C12 0.3(3) . . . . ? C9 C8 N2 Fe -176.58(15) . . . 1_545 ? C11 C12 N2 C8 -1.2(4) . . . . ? C11 C12 N2 Fe 175.7(2) . . . 1_545 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C9 H9 S 0.86(2) 2.79(2) 3.518(2) 143.1(19) 3_445 _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 31.07 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.504 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.044