# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 Fe N O S' _chemical_formula_sum 'C13 H15 Fe N O S' _chemical_formula_weight 289.17 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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 17.8607(17) _cell_length_b 7.3757(7) _cell_length_c 18.9368(18) _cell_angle_alpha 90.00 _cell_angle_beta 92.073(2) _cell_angle_gamma 90.00 _cell_volume 2493.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4717 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 25.29 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_min 0.104 _exptl_crystal_size_mid 0.192 _exptl_crystal_size_max 0.482 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 1.358 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6188 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details '(Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker Smart Apex CCD diffractometer 01-670' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 0.661 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8240 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.32 _reflns_number_total 2258 _reflns_number_gt 1980 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 7.34A (Bruker, 2006)' _computing_structure_solution 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V 6.12 (Sheldrick, 2000)' _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^)+(0.0414P)^2^+0.2315P] 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 2258 _refine_ls_number_parameters 206 _refine_ls_number_restraints 205 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0685 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.028 _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 0.321404(14) 0.16070(4) 0.371256(13) 0.03009(11) Uani 1 1 d D A . S1 S 0.53777(3) -0.00689(8) 0.34605(3) 0.04768(17) Uani 1 1 d . A . N1 N 0.51271(9) 0.2263(2) 0.44816(10) 0.0379(4) Uani 1 1 d . A . H1 H 0.4865(12) 0.273(3) 0.4774(11) 0.045 Uiso 1 1 d . . . O1 O 0.52881(11) 0.6015(2) 0.41961(9) 0.0571(5) Uani 1 1 d . . . H1A H 0.5271(17) 0.687(4) 0.3986(16) 0.086 Uiso 1 1 d . . . C1 C 0.40974(10) 0.0333(3) 0.42007(10) 0.0320(4) Uani 1 1 d . A . C2 C 0.36734(11) -0.0909(3) 0.37652(12) 0.0397(5) Uani 1 1 d . A . H2 H 0.3853 -0.1563 0.3387 0.048 Uiso 1 1 calc R . . C3 C 0.29399(12) -0.0972(3) 0.40056(13) 0.0440(5) Uani 1 1 d . A . H3 H 0.2552 -0.1675 0.3813 0.053 Uiso 1 1 calc R . . C4 C 0.28890(11) 0.0205(3) 0.45869(11) 0.0421(5) Uani 1 1 d . . . H4 H 0.2463 0.0409 0.4844 0.051 Uiso 1 1 calc R A . C5 C 0.35984(11) 0.1023(3) 0.47112(10) 0.0357(5) Uani 1 1 d . A . H5 H 0.3719 0.1863 0.5063 0.043 Uiso 1 1 calc R . . C6 C 0.3647(3) 0.3630(8) 0.3121(3) 0.0456(12) Uani 0.767(14) 1 d PDU A 1 H6 H 0.4152 0.3918 0.3095 0.055 Uiso 0.767(14) 1 calc PR A 1 C7 C 0.3249(3) 0.2393(8) 0.26816(18) 0.0454(11) Uani 0.767(14) 1 d PDU A 1 H7 H 0.3446 0.1724 0.2316 0.055 Uiso 0.767(14) 1 calc PR A 1 C8 C 0.2501(3) 0.2349(7) 0.2893(2) 0.0437(10) Uani 0.767(14) 1 d PDU A 1 H8 H 0.2118 0.1647 0.2689 0.052 Uiso 0.767(14) 1 calc PR A 1 C9 C 0.2433(3) 0.3557(8) 0.3468(2) 0.0416(10) Uani 0.767(14) 1 d PDU A 1 H9 H 0.1998 0.3786 0.3709 0.050 Uiso 0.767(14) 1 calc PR A 1 C10 C 0.3146(4) 0.4358(4) 0.3610(2) 0.0421(11) Uani 0.767(14) 1 d PDU A 1 H10 H 0.3262 0.5206 0.3961 0.051 Uiso 0.767(14) 1 calc PR A 1 C6B C 0.2418(7) 0.271(2) 0.3040(9) 0.042(2) Uani 0.233(14) 1 d PDU A 2 H6B H 0.1931 0.2288 0.2963 0.050 Uiso 0.233(14) 1 calc PR A 2 C7B C 0.2651(10) 0.3992(17) 0.3552(8) 0.039(2) Uani 0.233(14) 1 d PDU A 2 H7B H 0.2345 0.4558 0.3872 0.046 Uiso 0.233(14) 1 calc PR A 2 C8B C 0.3428(11) 0.4270(12) 0.3496(8) 0.039(2) Uani 0.233(14) 1 d PDU A 2 H8B H 0.3724 0.5048 0.3773 0.046 Uiso 0.233(14) 1 calc PR A 2 C9B C 0.3674(8) 0.316(2) 0.2944(8) 0.039(2) Uani 0.233(14) 1 d PDU A 2 H9B H 0.4162 0.3083 0.2791 0.047 Uiso 0.233(14) 1 calc PR A 2 C10B C 0.3048(11) 0.218(2) 0.2663(4) 0.042(2) Uani 0.233(14) 1 d PDU A 2 H10B H 0.3053 0.1344 0.2297 0.050 Uiso 0.233(14) 1 calc PR A 2 C11 C 0.48701(10) 0.0921(3) 0.40814(10) 0.0330(4) Uani 1 1 d . . . C12 C 0.58469(11) 0.3154(3) 0.44195(13) 0.0466(6) Uani 1 1 d . . . H12A H 0.6209 0.2289 0.4252 0.056 Uiso 1 1 calc R A . H12B H 0.6023 0.3576 0.4881 0.056 Uiso 1 1 calc R . . C13 C 0.57920(12) 0.4742(3) 0.39157(12) 0.0457(5) Uani 1 1 d . A . H13A H 0.6281 0.5291 0.3868 0.055 Uiso 1 1 calc R . . H13B H 0.5610 0.4339 0.3453 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.03068(17) 0.02722(18) 0.03215(18) 0.00076(12) -0.00186(11) 0.00208(11) S1 0.0461(3) 0.0457(3) 0.0523(3) 0.0016(3) 0.0154(3) 0.0041(3) N1 0.0319(9) 0.0352(10) 0.0465(11) 0.0018(8) 0.0015(8) -0.0002(8) O1 0.0784(12) 0.0369(10) 0.0566(11) 0.0048(8) 0.0135(9) 0.0054(9) C1 0.0307(9) 0.0268(10) 0.0382(10) 0.0069(8) -0.0038(8) 0.0038(8) C2 0.0415(12) 0.0240(10) 0.0532(13) 0.0003(10) -0.0014(10) 0.0028(9) C3 0.0365(11) 0.0305(11) 0.0643(15) 0.0060(11) -0.0047(10) -0.0060(9) C4 0.0338(11) 0.0474(13) 0.0454(12) 0.0141(10) 0.0046(9) -0.0022(9) C5 0.0372(11) 0.0391(12) 0.0307(10) 0.0078(9) -0.0006(8) 0.0010(9) C6 0.0445(16) 0.043(2) 0.050(2) 0.018(2) 0.0023(16) -0.0015(16) C7 0.052(2) 0.054(2) 0.0302(16) 0.0086(14) 0.0035(13) 0.007(2) C8 0.0446(18) 0.051(2) 0.0350(19) 0.0021(15) -0.0114(16) 0.0087(15) C9 0.0405(18) 0.040(2) 0.044(2) 0.0060(16) -0.0027(16) 0.0133(16) C10 0.054(3) 0.0258(15) 0.0462(18) 0.0056(12) -0.0056(19) 0.0052(14) C6B 0.041(3) 0.046(4) 0.038(4) 0.002(4) -0.008(3) 0.006(3) C7B 0.045(4) 0.033(4) 0.039(4) 0.001(3) 0.001(4) 0.009(4) C8B 0.045(4) 0.029(4) 0.041(4) 0.001(3) -0.004(4) 0.002(4) C9B 0.045(3) 0.036(5) 0.035(4) 0.005(4) 0.006(3) 0.004(4) C10B 0.051(5) 0.044(4) 0.030(4) -0.002(3) -0.007(3) 0.003(4) C11 0.0348(10) 0.0271(10) 0.0367(11) 0.0086(9) -0.0031(8) 0.0043(8) C12 0.0347(11) 0.0420(13) 0.0627(15) 0.0066(11) -0.0056(10) -0.0049(10) C13 0.0418(12) 0.0415(13) 0.0542(13) 0.0032(11) 0.0061(10) -0.0068(10) _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 C2 2.030(2) . ? Fe1 C1 2.0302(17) . ? Fe1 C5 2.0344(18) . ? Fe1 C6 2.035(3) . ? Fe1 C7 2.040(3) . ? Fe1 C10 2.041(3) . ? Fe1 C10B 2.043(7) . ? Fe1 C7B 2.044(7) . ? Fe1 C6B 2.044(7) . ? Fe1 C9 2.046(3) . ? Fe1 C8B 2.046(7) . ? Fe1 C3 2.046(2) . ? S1 C11 1.677(2) . ? N1 C11 1.319(3) . ? N1 C12 1.452(3) . ? O1 C13 1.417(3) . ? C1 C2 1.431(3) . ? C1 C5 1.432(3) . ? C1 C11 1.472(3) . ? C2 C3 1.403(3) . ? C3 C4 1.407(3) . ? C4 C5 1.415(3) . ? C6 C7 1.410(5) . ? C6 C10 1.417(5) . ? C7 C8 1.409(5) . ? C8 C9 1.416(5) . ? C9 C10 1.421(5) . ? C6B C7B 1.405(10) . ? C6B C10B 1.410(10) . ? C7B C8B 1.411(9) . ? C8B C9B 1.411(9) . ? C9B C10B 1.417(9) . ? C12 C13 1.512(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 C2 Fe1 C1 41.27(8) . . ? C2 Fe1 C5 68.82(8) . . ? C1 Fe1 C5 41.26(8) . . ? C2 Fe1 C6 122.4(2) . . ? C1 Fe1 C6 106.58(14) . . ? C5 Fe1 C6 122.99(18) . . ? C2 Fe1 C7 106.30(16) . . ? C1 Fe1 C7 121.15(16) . . ? C5 Fe1 C7 158.26(19) . . ? C6 Fe1 C7 40.49(16) . . ? C2 Fe1 C10 159.4(2) . . ? C1 Fe1 C10 123.11(18) . . ? C5 Fe1 C10 108.39(13) . . ? C6 Fe1 C10 40.69(14) . . ? C7 Fe1 C10 68.31(16) . . ? C2 Fe1 C10B 106.4(4) . . ? C1 Fe1 C10B 128.5(5) . . ? C5 Fe1 C10B 168.6(6) . . ? C6 Fe1 C10B 50.0(5) . . ? C7 Fe1 C10B 11.0(5) . . ? C10 Fe1 C10B 72.2(5) . . ? C2 Fe1 C7B 171.9(6) . . ? C1 Fe1 C7B 146.8(6) . . ? C5 Fe1 C7B 117.9(5) . . ? C6 Fe1 C7B 58.8(4) . . ? C7 Fe1 C7B 69.2(5) . . ? C10 Fe1 C7B 26.2(5) . . ? C10B Fe1 C7B 67.8(4) . . ? C2 Fe1 C6B 131.8(6) . . ? C1 Fe1 C6B 168.5(6) . . ? C5 Fe1 C6B 150.1(6) . . ? C6 Fe1 C6B 68.6(5) . . ? C7 Fe1 C6B 48.3(5) . . ? C10 Fe1 C6B 60.4(5) . . ? C10B Fe1 C6B 40.4(3) . . ? C7B Fe1 C6B 40.2(3) . . ? C2 Fe1 C9 157.7(2) . . ? C1 Fe1 C9 160.3(2) . . ? C5 Fe1 C9 124.34(15) . . ? C6 Fe1 C9 68.25(15) . . ? C7 Fe1 C9 68.11(16) . . ? C10 Fe1 C9 40.68(13) . . ? C10B Fe1 C9 63.9(5) . . ? C7B Fe1 C9 14.7(5) . . ? C6B Fe1 C9 28.9(5) . . ? C2 Fe1 C8B 144.1(6) . . ? C1 Fe1 C8B 112.9(5) . . ? C5 Fe1 C8B 109.3(4) . . ? C6 Fe1 C8B 26.9(4) . . ? C7 Fe1 C8B 61.5(4) . . ? C10 Fe1 C8B 15.7(4) . . ? C10B Fe1 C8B 68.1(4) . . ? C7B Fe1 C8B 40.4(3) . . ? C6B Fe1 C8B 67.8(4) . . ? C9 Fe1 C8B 53.8(4) . . ? C2 Fe1 C3 40.27(9) . . ? C1 Fe1 C3 68.64(8) . . ? C5 Fe1 C3 68.10(9) . . ? C6 Fe1 C3 158.5(2) . . ? C7 Fe1 C3 122.68(19) . . ? C10 Fe1 C3 159.3(2) . . ? C10B Fe1 C3 115.4(5) . . ? C7B Fe1 C3 136.0(6) . . ? C6B Fe1 C3 111.8(4) . . ? C9 Fe1 C3 123.2(2) . . ? C8B Fe1 C3 174.6(6) . . ? C11 N1 C12 125.7(2) . . ? C2 C1 C5 106.70(17) . . ? C2 C1 C11 125.43(18) . . ? C5 C1 C11 127.51(18) . . ? C2 C1 Fe1 69.36(11) . . ? C5 C1 Fe1 69.53(10) . . ? C11 C1 Fe1 120.75(13) . . ? C3 C2 C1 108.36(19) . . ? C3 C2 Fe1 70.47(12) . . ? C1 C2 Fe1 69.37(11) . . ? C2 C3 C4 108.72(18) . . ? C2 C3 Fe1 69.26(11) . . ? C4 C3 Fe1 70.22(12) . . ? C3 C4 C5 108.08(19) . . ? C3 C4 Fe1 69.63(12) . . ? C5 C4 Fe1 69.02(11) . . ? C4 C5 C1 108.14(18) . . ? C4 C5 Fe1 70.47(11) . . ? C1 C5 Fe1 69.21(10) . . ? C7 C6 C10 108.3(3) . . ? C7 C6 Fe1 69.95(18) . . ? C10 C6 Fe1 69.91(19) . . ? C8 C7 C6 108.1(4) . . ? C8 C7 Fe1 70.11(18) . . ? C6 C7 Fe1 69.57(19) . . ? C7 C8 C9 108.2(3) . . ? C7 C8 Fe1 69.55(18) . . ? C9 C8 Fe1 69.70(16) . . ? C8 C9 C10 107.9(3) . . ? C8 C9 Fe1 69.82(18) . . ? C10 C9 Fe1 69.50(17) . . ? C6 C10 C9 107.5(3) . . ? C6 C10 Fe1 69.40(17) . . ? C9 C10 Fe1 69.82(18) . . ? C7B C6B C10B 108.3(8) . . ? C7B C6B Fe1 69.9(4) . . ? C10B C6B Fe1 69.8(4) . . ? C6B C7B C8B 108.3(7) . . ? C6B C7B Fe1 69.9(4) . . ? C8B C7B Fe1 69.9(4) . . ? C9B C8B C7B 107.8(7) . . ? C9B C8B Fe1 69.9(4) . . ? C7B C8B Fe1 69.7(4) . . ? C8B C9B C10B 108.1(8) . . ? C8B C9B Fe1 69.8(4) . . ? C10B C9B Fe1 69.6(4) . . ? C6B C10B C9B 107.7(8) . . ? C6B C10B Fe1 69.9(4) . . ? C9B C10B Fe1 69.9(4) . . ? N1 C11 C1 116.20(18) . . ? N1 C11 S1 122.93(16) . . ? C1 C11 S1 120.87(15) . . ? N1 C12 C13 111.35(17) . . ? O1 C13 C12 107.73(19) . . ? 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 N1 H1 O1 0.81(2) 2.18(2) 2.927(3) 152(2) 5_666 O1 H1A S1 0.74(3) 2.48(3) 3.2132(18) 169(3) 1_565 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.256 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 923983' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_4-Pd(PPh3Cl) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H28 Cl2 Fe N P Pd S, C H Cl3' _chemical_formula_sum 'C32 H29 Cl5 Fe N P Pd S' _chemical_formula_weight 830.09 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' P P 0.1023 0.0942 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.1372(10) _cell_length_b 14.8178(12) _cell_length_c 19.7325(16) _cell_angle_alpha 90.00 _cell_angle_beta 105.8430(10) _cell_angle_gamma 90.00 _cell_volume 3414.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9545 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 25.34 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_min 0.102 _exptl_crystal_size_mid 0.256 _exptl_crystal_size_max 0.422 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 1.475 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6109 _exptl_absorpt_correction_T_max 0.8630 _exptl_absorpt_process_details '(Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker Smart Apex CCD diffractometer' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 0.661 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 36660 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.37 _reflns_number_total 6244 _reflns_number_gt 5534 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 6.23C (Bruker, 1999)' _computing_structure_solution 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V 6.12 (Sheldrick, 2000)' _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^)+(0.0385P)^2^+1.4243P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6244 _refine_ls_number_parameters 453 _refine_ls_number_restraints 230 _refine_ls_R_factor_all 0.0329 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0698 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.093 _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 Pd1 Pd 0.515156(15) 0.354255(12) 0.426459(9) 0.03779(7) Uani 1 1 d . . . Cl1 Cl 0.42987(7) 0.39821(5) 0.31315(4) 0.0630(2) Uani 1 1 d . . . Cl2 Cl 0.67347(6) 0.45043(5) 0.43538(4) 0.05979(19) Uani 1 1 d . . . P1 P 0.36600(5) 0.26078(4) 0.41604(3) 0.03710(14) Uani 1 1 d . . . C1 C 0.7012(2) 0.19254(19) 0.51230(15) 0.0492(6) Uani 1 1 d . A . C2 C 0.7350(3) 0.1031(2) 0.5355(2) 0.0739(10) Uani 1 1 d . A . H2 H 0.7330 0.0766 0.5807 0.089 Uiso 1 1 calc R . . C3 C 0.7704(3) 0.0595(3) 0.4819(3) 0.0963(14) Uani 1 1 d . A . H3 H 0.7995 -0.0024 0.4839 0.116 Uiso 1 1 calc R . . C4 C 0.7604(3) 0.1191(3) 0.4265(2) 0.0897(13) Uani 1 1 d . A . H4 H 0.7814 0.1063 0.3830 0.108 Uiso 1 1 calc R . . C5 C 0.7178(3) 0.2027(3) 0.44422(16) 0.0671(9) Uani 1 1 d . A . H5 H 0.7023 0.2570 0.4148 0.081 Uiso 1 1 calc R . . Fe1 Fe 0.86673(4) 0.17173(3) 0.51650(3) 0.06274(13) Uani 1 1 d D . . C6 C 0.9755(13) 0.2599(10) 0.5803(8) 0.094(4) Uani 0.57(3) 1 d PDU A 1 H6 H 0.9543 0.3114 0.6006 0.113 Uiso 0.57(3) 1 calc PR A 1 C7 C 0.9905(11) 0.1745(12) 0.6101(5) 0.089(3) Uani 0.57(3) 1 d PDU A 1 H7 H 0.9802 0.1584 0.6536 0.107 Uiso 0.57(3) 1 calc PR A 1 C8 C 1.0243(9) 0.1162(12) 0.5629(6) 0.082(3) Uani 0.57(3) 1 d PDU A 1 H8 H 1.0415 0.0552 0.5701 0.099 Uiso 0.57(3) 1 calc PR A 1 C9 C 1.0270(9) 0.1660(15) 0.5040(7) 0.092(4) Uani 0.57(3) 1 d PDU A 1 H9 H 1.0452 0.1437 0.4643 0.110 Uiso 0.57(3) 1 calc PR A 1 C10 C 0.9978(13) 0.2555(12) 0.5143(8) 0.101(4) Uani 0.57(3) 1 d PDU A 1 H10 H 0.9940 0.3031 0.4831 0.122 Uiso 0.57(3) 1 calc PR A 1 C6B C 0.9436(18) 0.2804(12) 0.5769(9) 0.096(4) Uani 0.43(3) 1 d PDU A 2 H6B H 0.9061 0.3225 0.5976 0.115 Uiso 0.43(3) 1 calc PR A 2 C7B C 0.9920(17) 0.2008(18) 0.6066(8) 0.111(6) Uani 0.43(3) 1 d PDU A 2 H7B H 0.9938 0.1803 0.6515 0.133 Uiso 0.43(3) 1 calc PR A 2 C8B C 1.0387(11) 0.155(2) 0.5579(11) 0.107(5) Uani 0.43(3) 1 d PDU A 2 H8B H 1.0765 0.0999 0.5647 0.129 Uiso 0.43(3) 1 calc PR A 2 C9B C 1.0166(16) 0.210(2) 0.4971(12) 0.113(6) Uani 0.43(3) 1 d PDU A 2 H9B H 1.0358 0.1969 0.4556 0.135 Uiso 0.43(3) 1 calc PR A 2 C10B C 0.9609(18) 0.2862(13) 0.5108(10) 0.099(4) Uani 0.43(3) 1 d PDU A 2 H10B H 0.9384 0.3344 0.4799 0.119 Uiso 0.43(3) 1 calc PR A 2 S11 S 0.70892(7) 0.25417(7) 0.64534(4) 0.0674(2) Uani 1 1 d . A . C12 C 0.6594(2) 0.25877(17) 0.55335(12) 0.0415(6) Uani 1 1 d . . . N13 N 0.58782(17) 0.32146(14) 0.52822(10) 0.0387(4) Uani 1 1 d . A . C14 C 0.5683(3) 0.3833(2) 0.58227(15) 0.0556(7) Uani 1 1 d . . . H14A H 0.4886 0.4018 0.5702 0.067 Uiso 1 1 calc R A . H14B H 0.6155 0.4368 0.5854 0.067 Uiso 1 1 calc R . . C15 C 0.5993(3) 0.3331(2) 0.65203(15) 0.0672(9) Uani 1 1 d . A . H15A H 0.5332 0.3017 0.6591 0.081 Uiso 1 1 calc R . . H15B H 0.6281 0.3745 0.6909 0.081 Uiso 1 1 calc R . . C16 C 0.3595(2) 0.16857(17) 0.35427(13) 0.0432(6) Uani 1 1 d . . . C17 C 0.4324(3) 0.1646(2) 0.31148(15) 0.0563(7) Uani 1 1 d . . . H17 H 0.4860 0.2100 0.3131 0.068 Uiso 1 1 calc R . . C18 C 0.4246(3) 0.0918(2) 0.26600(16) 0.0706(9) Uani 1 1 d . . . H18 H 0.4743 0.0883 0.2376 0.085 Uiso 1 1 calc R . . C19 C 0.3456(3) 0.0256(2) 0.26236(17) 0.0745(10) Uani 1 1 d . . . H19 H 0.3407 -0.0220 0.2310 0.089 Uiso 1 1 calc R . . C20 C 0.2731(3) 0.0287(2) 0.30469(16) 0.0638(9) Uani 1 1 d . . . H20 H 0.2189 -0.0166 0.3020 0.077 Uiso 1 1 calc R . . C21 C 0.2807(3) 0.09896(18) 0.35112(14) 0.0522(7) Uani 1 1 d . . . H21 H 0.2329 0.1002 0.3808 0.063 Uiso 1 1 calc R . . C22 C 0.2290(2) 0.31922(17) 0.39133(13) 0.0430(6) Uani 1 1 d . . . C23 C 0.1339(2) 0.2884(2) 0.34096(15) 0.0551(7) Uani 1 1 d . . . H23 H 0.1389 0.2366 0.3154 0.066 Uiso 1 1 calc R . . C24 C 0.0310(3) 0.3345(2) 0.32835(19) 0.0712(9) Uani 1 1 d . . . H24 H -0.0328 0.3132 0.2944 0.085 Uiso 1 1 calc R . . C25 C 0.0224(3) 0.4111(3) 0.3655(2) 0.0725(9) Uani 1 1 d . . . H25 H -0.0472 0.4411 0.3573 0.087 Uiso 1 1 calc R . . C26 C 0.1168(3) 0.4431(2) 0.41449(18) 0.0652(8) Uani 1 1 d . . . H26 H 0.1114 0.4954 0.4395 0.078 Uiso 1 1 calc R . . C27 C 0.2199(2) 0.39841(18) 0.42711(15) 0.0533(7) Uani 1 1 d . . . H27 H 0.2839 0.4214 0.4599 0.064 Uiso 1 1 calc R . . C28 C 0.3700(2) 0.20140(16) 0.49770(12) 0.0389(5) Uani 1 1 d . . . C29 C 0.3115(2) 0.2310(2) 0.54499(14) 0.0525(7) Uani 1 1 d . . . H29 H 0.2628 0.2805 0.5341 0.063 Uiso 1 1 calc R . . C30 C 0.3259(3) 0.1864(2) 0.60844(16) 0.0626(8) Uani 1 1 d . . . H30A H 0.2855 0.2058 0.6396 0.075 Uiso 1 1 calc R . . C31 C 0.3978(3) 0.1151(2) 0.62589(15) 0.0596(8) Uani 1 1 d . . . H31 H 0.4076 0.0867 0.6691 0.072 Uiso 1 1 calc R . . C32 C 0.4565(2) 0.0846(2) 0.57970(15) 0.0526(7) Uani 1 1 d . . . H32 H 0.5056 0.0354 0.5915 0.063 Uiso 1 1 calc R . . C33 C 0.4421(2) 0.12748(18) 0.51585(14) 0.0451(6) Uani 1 1 d . . . H33 H 0.4814 0.1066 0.4845 0.054 Uiso 1 1 calc R . . C34 C 0.6602(3) 0.5311(2) 0.27544(17) 0.0900(12) Uani 1 1 d D . . H34 H 0.6253 0.5139 0.3129 0.108 Uiso 1 1 calc R B 1 Cl3 Cl 0.7073(6) 0.4320(5) 0.2445(4) 0.129(2) Uani 0.620(17) 1 d PDU C 1 Cl4 Cl 0.5566(6) 0.5912(7) 0.2122(3) 0.156(3) Uani 0.620(17) 1 d PDU C 1 Cl5 Cl 0.7801(3) 0.5994(3) 0.3145(3) 0.1279(15) Uani 0.620(17) 1 d PDU C 1 Cl3B Cl 0.7300(8) 0.4534(5) 0.2333(4) 0.0870(18) Uani 0.380(17) 1 d PDU C 2 Cl4B Cl 0.5417(9) 0.5620(12) 0.2028(6) 0.177(5) Uani 0.380(17) 1 d PDU C 2 Cl5B Cl 0.7519(12) 0.6247(8) 0.3005(7) 0.185(4) Uani 0.380(17) 1 d PDU C 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 Pd1 0.03828(12) 0.03529(11) 0.03561(11) 0.00275(7) 0.00297(8) -0.00044(8) Cl1 0.0648(5) 0.0669(5) 0.0470(4) 0.0207(3) -0.0022(3) -0.0019(4) Cl2 0.0572(4) 0.0574(4) 0.0610(4) 0.0024(3) 0.0096(3) -0.0173(3) P1 0.0373(3) 0.0358(3) 0.0337(3) -0.0001(2) 0.0020(2) -0.0004(3) C1 0.0363(13) 0.0488(15) 0.0580(17) -0.0043(13) 0.0051(12) 0.0044(12) C2 0.0585(19) 0.0539(19) 0.116(3) 0.0115(19) 0.034(2) 0.0080(15) C3 0.071(2) 0.065(2) 0.159(4) -0.022(3) 0.043(3) 0.010(2) C4 0.066(2) 0.111(3) 0.091(3) -0.040(3) 0.019(2) 0.019(2) C5 0.0556(18) 0.089(2) 0.0529(17) -0.0083(16) 0.0083(14) 0.0216(17) Fe1 0.0403(2) 0.0756(3) 0.0716(3) 0.0112(2) 0.0140(2) 0.0071(2) C6 0.035(7) 0.105(7) 0.126(7) -0.022(6) -0.005(5) -0.013(6) C7 0.038(5) 0.140(8) 0.077(5) 0.010(5) -0.006(4) 0.009(5) C8 0.036(4) 0.104(7) 0.101(6) 0.018(5) 0.010(4) 0.010(4) C9 0.044(4) 0.136(10) 0.098(6) 0.015(6) 0.023(5) 0.004(5) C10 0.048(8) 0.116(9) 0.132(7) 0.038(7) 0.011(7) -0.009(7) C6B 0.034(8) 0.124(9) 0.126(8) 0.004(7) 0.016(6) -0.021(6) C7B 0.068(10) 0.149(14) 0.111(9) 0.026(8) 0.015(8) -0.003(10) C8B 0.036(5) 0.141(12) 0.142(10) 0.034(10) 0.018(7) 0.011(7) C9B 0.063(9) 0.146(16) 0.147(10) 0.028(11) 0.059(8) -0.007(11) C10B 0.041(8) 0.124(9) 0.131(8) 0.033(8) 0.021(6) -0.014(6) S11 0.0645(5) 0.0875(6) 0.0392(4) 0.0065(4) -0.0043(3) 0.0019(4) C12 0.0363(13) 0.0487(14) 0.0349(12) 0.0019(11) 0.0019(10) -0.0036(11) N13 0.0386(11) 0.0404(11) 0.0345(10) -0.0045(9) 0.0053(9) -0.0026(9) C14 0.0627(18) 0.0545(16) 0.0480(16) -0.0164(13) 0.0125(14) -0.0015(14) C15 0.069(2) 0.089(2) 0.0410(16) -0.0150(15) 0.0102(14) -0.0095(18) C16 0.0491(15) 0.0404(13) 0.0335(12) -0.0016(10) 0.0002(11) 0.0036(11) C17 0.0636(19) 0.0572(17) 0.0460(15) -0.0009(13) 0.0112(14) 0.0093(14) C18 0.088(2) 0.075(2) 0.0488(17) -0.0068(16) 0.0192(17) 0.021(2) C19 0.102(3) 0.057(2) 0.0485(18) -0.0147(15) -0.0071(18) 0.0171(19) C20 0.080(2) 0.0461(16) 0.0489(17) -0.0074(13) -0.0096(16) -0.0011(15) C21 0.0598(17) 0.0473(15) 0.0409(14) -0.0030(12) -0.0006(12) -0.0044(13) C22 0.0412(13) 0.0419(13) 0.0409(13) 0.0063(11) 0.0027(11) 0.0001(11) C23 0.0474(16) 0.0581(17) 0.0497(16) 0.0005(13) -0.0036(12) 0.0007(13) C24 0.0453(17) 0.081(2) 0.072(2) 0.0077(18) -0.0101(15) 0.0019(16) C25 0.0507(18) 0.078(2) 0.083(2) 0.020(2) 0.0098(17) 0.0200(17) C26 0.065(2) 0.0536(18) 0.075(2) 0.0057(16) 0.0152(17) 0.0160(15) C27 0.0498(16) 0.0444(15) 0.0589(17) 0.0001(13) 0.0034(13) 0.0040(12) C28 0.0360(12) 0.0395(13) 0.0372(12) -0.0006(10) 0.0033(10) -0.0063(10) C29 0.0532(16) 0.0559(17) 0.0482(15) 0.0008(13) 0.0139(13) 0.0062(13) C30 0.068(2) 0.075(2) 0.0499(17) 0.0037(15) 0.0254(15) 0.0020(17) C31 0.0654(19) 0.0657(19) 0.0449(16) 0.0134(14) 0.0102(14) -0.0044(16) C32 0.0529(16) 0.0480(15) 0.0516(16) 0.0106(13) 0.0055(13) 0.0023(13) C33 0.0424(14) 0.0463(14) 0.0446(14) 0.0027(11) 0.0083(11) 0.0019(11) C34 0.098(3) 0.104(3) 0.081(3) 0.020(2) 0.046(2) 0.035(2) Cl3 0.078(2) 0.186(4) 0.124(3) -0.067(3) 0.0309(18) 0.005(2) Cl4 0.126(3) 0.221(5) 0.144(3) 0.104(3) 0.074(2) 0.107(4) Cl5 0.116(3) 0.0771(19) 0.204(3) 0.013(2) 0.0651(19) 0.0100(14) Cl3B 0.068(3) 0.101(3) 0.093(3) -0.018(2) 0.025(2) 0.023(2) Cl4B 0.113(4) 0.245(10) 0.190(7) 0.143(7) 0.069(4) 0.048(5) Cl5B 0.296(10) 0.072(4) 0.186(7) -0.025(4) 0.063(6) 0.005(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 Pd1 N13 2.020(2) . ? Pd1 P1 2.2439(7) . ? Pd1 Cl1 2.2871(7) . ? Pd1 Cl2 2.3600(7) . ? P1 C16 1.818(3) . ? P1 C22 1.819(3) . ? P1 C28 1.825(2) . ? C1 C5 1.420(4) . ? C1 C2 1.425(4) . ? C1 C12 1.449(4) . ? C1 Fe1 2.012(3) . ? C2 C3 1.403(6) . ? C2 Fe1 2.015(3) . ? C3 C4 1.384(6) . ? C3 Fe1 2.040(4) . ? C4 C5 1.422(5) . ? C4 Fe1 2.043(4) . ? C5 Fe1 2.026(3) . ? Fe1 C10 2.028(10) . ? Fe1 C9 2.029(9) . ? Fe1 C6 2.032(9) . ? Fe1 C8B 2.038(12) . ? Fe1 C9B 2.038(13) . ? Fe1 C7 2.039(8) . ? Fe1 C7B 2.046(14) . ? C6 C7 1.388(12) . ? C6 C10 1.401(13) . ? C7 C8 1.410(11) . ? C8 C9 1.384(11) . ? C9 C10 1.402(12) . ? C6B C7B 1.376(14) . ? C6B C10B 1.380(14) . ? C7B C8B 1.413(14) . ? C8B C9B 1.413(14) . ? C9B C10B 1.382(14) . ? S11 C12 1.751(2) . ? S11 C15 1.803(4) . ? C12 N13 1.276(3) . ? N13 C14 1.474(3) . ? C14 C15 1.519(4) . ? C16 C17 1.382(4) . ? C16 C21 1.396(4) . ? C17 C18 1.390(4) . ? C18 C19 1.361(5) . ? C19 C20 1.369(5) . ? C20 C21 1.373(4) . ? C22 C23 1.379(4) . ? C22 C27 1.389(4) . ? C23 C24 1.385(4) . ? C24 C25 1.370(5) . ? C25 C26 1.367(5) . ? C26 C27 1.377(4) . ? C28 C33 1.387(4) . ? C28 C29 1.389(4) . ? C29 C30 1.384(4) . ? C30 C31 1.354(5) . ? C31 C32 1.378(4) . ? C32 C33 1.379(4) . ? C34 Cl3 1.745(4) . ? C34 Cl4 1.752(4) . ? C34 Cl5B 1.763(5) . ? C34 Cl3B 1.767(4) . ? C34 Cl5 1.767(4) . ? C34 Cl4B 1.791(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 N13 Pd1 P1 93.72(6) . . ? N13 Pd1 Cl1 177.07(6) . . ? P1 Pd1 Cl1 87.00(3) . . ? N13 Pd1 Cl2 86.88(6) . . ? P1 Pd1 Cl2 178.60(3) . . ? Cl1 Pd1 Cl2 92.46(3) . . ? C16 P1 C22 107.97(12) . . ? C16 P1 C28 102.44(11) . . ? C22 P1 C28 105.54(12) . . ? C16 P1 Pd1 114.31(9) . . ? C22 P1 Pd1 112.72(9) . . ? C28 P1 Pd1 112.99(8) . . ? C5 C1 C2 107.5(3) . . ? C5 C1 C12 128.2(3) . . ? C2 C1 C12 124.3(3) . . ? C5 C1 Fe1 69.95(17) . . ? C2 C1 Fe1 69.39(17) . . ? C12 C1 Fe1 125.35(19) . . ? C3 C2 C1 107.8(4) . . ? C3 C2 Fe1 70.7(2) . . ? C1 C2 Fe1 69.14(17) . . ? C4 C3 C2 108.9(3) . . ? C4 C3 Fe1 70.3(2) . . ? C2 C3 Fe1 68.8(2) . . ? C3 C4 C5 108.8(4) . . ? C3 C4 Fe1 70.1(3) . . ? C5 C4 Fe1 68.9(2) . . ? C1 C5 C4 107.1(3) . . ? C1 C5 Fe1 68.88(16) . . ? C4 C5 Fe1 70.2(2) . . ? C1 Fe1 C2 41.46(12) . . ? C1 Fe1 C5 41.18(12) . . ? C2 Fe1 C5 69.19(16) . . ? C1 Fe1 C10 133.3(6) . . ? C2 Fe1 C10 168.6(6) . . ? C5 Fe1 C10 113.6(5) . . ? C1 Fe1 C9 169.0(5) . . ? C2 Fe1 C9 146.9(6) . . ? C5 Fe1 C9 128.7(4) . . ? C10 Fe1 C9 40.4(3) . . ? C1 Fe1 C6 113.6(5) . . ? C2 Fe1 C6 128.6(5) . . ? C5 Fe1 C6 126.5(5) . . ? C10 Fe1 C6 40.4(4) . . ? C9 Fe1 C6 67.6(4) . . ? C1 Fe1 C8B 159.5(6) . . ? C2 Fe1 C8B 130.0(8) . . ? C5 Fe1 C8B 158.3(7) . . ? C10 Fe1 C8B 50.1(6) . . ? C1 Fe1 C9B 151.9(9) . . ? C2 Fe1 C9B 165.7(9) . . ? C5 Fe1 C9B 118.4(8) . . ? C8B Fe1 C9B 40.6(4) . . ? C1 Fe1 C7 121.0(4) . . ? C2 Fe1 C7 105.5(5) . . ? C5 Fe1 C7 158.2(4) . . ? C10 Fe1 C7 67.6(5) . . ? C9 Fe1 C7 67.5(5) . . ? C6 Fe1 C7 39.9(4) . . ? C1 Fe1 C3 68.67(13) . . ? C2 Fe1 C3 40.48(16) . . ? C5 Fe1 C3 68.26(18) . . ? C10 Fe1 C3 150.8(6) . . ? C9 Fe1 C3 114.0(6) . . ? C6 Fe1 C3 161.4(5) . . ? C8B Fe1 C3 117.8(9) . . ? C9B Fe1 C3 128.5(7) . . ? C7 Fe1 C3 122.2(5) . . ? C1 Fe1 C4 68.64(13) . . ? C2 Fe1 C4 67.90(19) . . ? C5 Fe1 C4 40.92(15) . . ? C10 Fe1 C4 121.9(5) . . ? C9 Fe1 C4 106.1(4) . . ? C6 Fe1 C4 159.0(5) . . ? C8B Fe1 C4 129.6(7) . . ? C9B Fe1 C4 109.1(6) . . ? C7 Fe1 C4 158.3(5) . . ? C3 Fe1 C4 39.62(18) . . ? C1 Fe1 C7B 120.0(7) . . ? C2 Fe1 C7B 112.6(7) . . ? C5 Fe1 C7B 150.8(7) . . ? C8B Fe1 C7B 40.5(5) . . ? C9B Fe1 C7B 67.4(7) . . ? C3 Fe1 C7B 133.2(8) . . ? C4 Fe1 C7B 168.3(7) . . ? C7 C6 C10 108.4(8) . . ? C7 C6 Fe1 70.4(6) . . ? C10 C6 Fe1 69.7(5) . . ? C6 C7 C8 107.8(9) . . ? C6 C7 Fe1 69.8(5) . . ? C8 C7 Fe1 70.4(5) . . ? C9 C8 C7 107.9(9) . . ? C9 C8 Fe1 69.2(5) . . ? C7 C8 Fe1 69.3(5) . . ? C8 C9 C10 108.5(9) . . ? C8 C9 Fe1 71.1(5) . . ? C10 C9 Fe1 69.7(6) . . ? C6 C10 C9 107.4(9) . . ? C6 C10 Fe1 70.0(5) . . ? C9 C10 Fe1 69.8(6) . . ? C7B C6B C10B 107.4(11) . . ? C7B C6B Fe1 69.6(7) . . ? C10B C6B Fe1 70.4(7) . . ? C6B C7B C8B 108.9(11) . . ? C6B C7B Fe1 71.3(8) . . ? C8B C7B Fe1 69.4(7) . . ? C9B C8B C7B 106.6(12) . . ? C9B C8B Fe1 69.7(7) . . ? C7B C8B Fe1 70.1(8) . . ? C10B C9B C8B 107.0(11) . . ? C10B C9B Fe1 71.4(7) . . ? C8B C9B Fe1 69.7(7) . . ? C6B C10B C9B 110.0(11) . . ? C6B C10B Fe1 70.6(6) . . ? C9B C10B Fe1 69.3(7) . . ? C12 S11 C15 89.98(13) . . ? N13 C12 C1 125.5(2) . . ? N13 C12 S11 115.82(19) . . ? C1 C12 S11 118.67(19) . . ? C12 N13 C14 113.5(2) . . ? C12 N13 Pd1 128.87(17) . . ? C14 N13 Pd1 117.20(17) . . ? N13 C14 C15 107.6(2) . . ? C14 C15 S11 104.9(2) . . ? C17 C16 C21 119.1(3) . . ? C17 C16 P1 121.6(2) . . ? C21 C16 P1 119.3(2) . . ? C16 C17 C18 119.0(3) . . ? C19 C18 C17 121.1(3) . . ? C18 C19 C20 120.3(3) . . ? C19 C20 C21 119.7(3) . . ? C20 C21 C16 120.7(3) . . ? C23 C22 C27 118.6(3) . . ? C23 C22 P1 124.0(2) . . ? C27 C22 P1 117.37(19) . . ? C22 C23 C24 120.2(3) . . ? C25 C24 C23 120.6(3) . . ? C26 C25 C24 119.7(3) . . ? C25 C26 C27 120.3(3) . . ? C26 C27 C22 120.6(3) . . ? C33 C28 C29 118.6(2) . . ? C33 C28 P1 118.11(19) . . ? C29 C28 P1 123.1(2) . . ? C30 C29 C28 119.7(3) . . ? C31 C30 C29 121.1(3) . . ? C30 C31 C32 120.1(3) . . ? C31 C32 C33 119.6(3) . . ? C32 C33 C28 120.9(3) . . ? Cl3 C34 Cl4 114.7(5) . . ? Cl5B C34 Cl3B 107.3(4) . . ? Cl3 C34 Cl5 108.9(3) . . ? Cl4 C34 Cl5 111.4(4) . . ? Cl5B C34 Cl4B 109.4(6) . . ? Cl3B C34 Cl4B 100.0(5) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.690 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 923984' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_5c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 Fe N S2' _chemical_formula_sum 'C19 H17 Fe N S2' _chemical_formula_weight 379.31 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 7.3639(14) _cell_length_b 9.2452(17) _cell_length_c 25.189(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.759(3) _cell_angle_gamma 90.00 _cell_volume 1714.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3466 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.08 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_min 0.222 _exptl_crystal_size_mid 0.292 _exptl_crystal_size_max 0.314 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 1.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5671 _exptl_absorpt_correction_T_max 0.8257 _exptl_absorpt_process_details '(Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker Smart Apex CCD diffractometer 01-670' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 0.661 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9131 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.34 _reflns_number_total 3120 _reflns_number_gt 2326 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 7.34A (Bruker, 2006)' _computing_structure_solution 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V 6.12 (Sheldrick, 2000)' _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^)+(0.0593P)^2^+0.1638P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3120 _refine_ls_number_parameters 245 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1105 _refine_ls_wR_factor_gt 0.1009 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.30824(6) 0.99229(5) 0.116898(16) 0.05863(18) Uani 1 1 d . . . C1 C 0.4455(4) 0.8211(3) 0.08763(11) 0.0585(7) Uani 1 1 d . A . C2 C 0.4216(4) 0.8070(3) 0.14412(11) 0.0612(8) Uani 1 1 d . . . C3 C 0.5084(4) 0.9276(4) 0.16909(12) 0.0653(8) Uani 1 1 d . . . H3 H 0.5132 0.9475 0.2073 0.078 Uiso 1 1 calc R . . C4 C 0.5839(4) 1.0147(3) 0.12965(14) 0.0676(9) Uani 1 1 d . . . H4 H 0.6485 1.1061 0.1358 0.081 Uiso 1 1 calc R . . C5 C 0.5460(4) 0.9505(3) 0.07956(13) 0.0622(8) Uani 1 1 d . . . H5 H 0.5805 0.9895 0.0451 0.075 Uiso 1 1 calc R . . C6 C 0.0615(5) 1.0014(5) 0.07888(18) 0.0915(13) Uani 1 1 d . . . H6 H 0.0127 0.9311 0.0530 0.110 Uiso 1 1 calc R . . C7 C 0.0405(5) 0.9973(5) 0.13451(18) 0.0902(12) Uani 1 1 d . . . H7 H -0.0250 0.9234 0.1542 0.108 Uiso 1 1 calc R . . C8 C 0.1285(5) 1.1172(5) 0.15617(15) 0.0874(11) Uani 1 1 d . . . H8 H 0.1368 1.1417 0.1940 0.105 Uiso 1 1 calc R . . C9 C 0.2026(5) 1.1970(4) 0.11540(15) 0.0852(10) Uani 1 1 d . . . H9 H 0.2720 1.2870 0.1196 0.102 Uiso 1 1 calc R . . C10 C 0.1620(5) 1.1260(5) 0.06732(15) 0.0866(11) Uani 1 1 d . . . H10 H 0.1970 1.1578 0.0320 0.104 Uiso 1 1 calc R . . C11 C 0.3765(4) 0.7308(3) 0.04358(12) 0.0660(8) Uani 1 1 d D . . S12 S 0.2404(9) 0.5765(7) 0.0554(3) 0.0908(13) Uani 0.607(17) 1 d PDU A 1 C13 C 0.2506(16) 0.5258(13) -0.0131(4) 0.091(2) Uani 0.607(17) 1 d PU A 1 H13A H 0.3413 0.4512 -0.0179 0.109 Uiso 0.607(17) 1 calc PR A 1 H13B H 0.1338 0.4902 -0.0263 0.109 Uiso 0.607(17) 1 calc PR A 1 C14 C 0.3044(17) 0.6696(14) -0.0429(4) 0.087(2) Uani 0.607(17) 1 d PU A 1 H14A H 0.3798 0.6470 -0.0727 0.105 Uiso 0.607(17) 1 calc PR A 1 H14B H 0.1961 0.7189 -0.0562 0.105 Uiso 0.607(17) 1 calc PR A 1 N15 N 0.4033(15) 0.7609(16) -0.0052(2) 0.080(2) Uani 0.607(17) 1 d PDU A 1 S12B S 0.1926(14) 0.6132(14) 0.0486(5) 0.098(2) Uani 0.393(17) 1 d PDU A 2 C13B C 0.207(2) 0.579(2) -0.0227(7) 0.086(3) Uani 0.393(17) 1 d PU A 2 H13C H 0.2106 0.4754 -0.0295 0.103 Uiso 0.393(17) 1 calc PR A 2 H13D H 0.1020 0.6190 -0.0417 0.103 Uiso 0.393(17) 1 calc PR A 2 C14B C 0.377(2) 0.649(2) -0.0404(6) 0.084(3) Uani 0.393(17) 1 d PU A 2 H14C H 0.4629 0.5746 -0.0501 0.101 Uiso 0.393(17) 1 calc PR A 2 H14D H 0.3494 0.7065 -0.0719 0.101 Uiso 0.393(17) 1 calc PR A 2 N15B N 0.462(2) 0.742(2) 0.0001(4) 0.075(3) Uani 0.393(17) 1 d PDU A 2 S16 S 0.31228(10) 0.66856(10) 0.17827(3) 0.0718(3) Uani 1 1 d . . . C17 C 0.4890(4) 0.5401(3) 0.18930(11) 0.0602(8) Uani 1 1 d . . . C18 C 0.4472(5) 0.4195(4) 0.21894(13) 0.0754(9) Uani 1 1 d . . . H18 H 0.3311 0.4095 0.2320 0.090 Uiso 1 1 calc R . . C19 C 0.5743(6) 0.3144(4) 0.22941(14) 0.0864(10) Uani 1 1 d . . . H19 H 0.5443 0.2343 0.2497 0.104 Uiso 1 1 calc R . . C20 C 0.7457(6) 0.3269(4) 0.21017(14) 0.0845(11) Uani 1 1 d . . . H20 H 0.8318 0.2553 0.2173 0.101 Uiso 1 1 calc R . . C21 C 0.7898(5) 0.4452(4) 0.18043(14) 0.0803(10) Uani 1 1 d . . . H21 H 0.9058 0.4533 0.1671 0.096 Uiso 1 1 calc R . . C22 C 0.6619(4) 0.5535(4) 0.16997(13) 0.0708(9) Uani 1 1 d . . . H22 H 0.6927 0.6342 0.1501 0.085 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0503(3) 0.0756(3) 0.0498(3) -0.00108(19) -0.00233(18) 0.0119(2) C1 0.0502(16) 0.0707(19) 0.0544(17) -0.0049(14) 0.0020(13) 0.0072(15) C2 0.0512(16) 0.077(2) 0.0551(17) 0.0030(15) -0.0002(13) 0.0148(15) C3 0.0585(18) 0.084(2) 0.0525(18) -0.0066(16) -0.0134(15) 0.0143(17) C4 0.0503(17) 0.073(2) 0.079(2) -0.0122(17) -0.0069(16) 0.0045(15) C5 0.0479(16) 0.077(2) 0.0617(19) -0.0034(16) 0.0056(14) 0.0005(15) C6 0.058(2) 0.123(3) 0.092(3) -0.012(2) -0.026(2) 0.024(2) C7 0.0460(18) 0.123(3) 0.102(3) 0.030(3) 0.0075(19) 0.022(2) C8 0.074(2) 0.114(3) 0.075(2) -0.001(2) 0.0103(19) 0.037(2) C9 0.083(2) 0.082(2) 0.090(3) 0.004(2) -0.001(2) 0.028(2) C10 0.080(2) 0.108(3) 0.072(2) 0.018(2) -0.0060(19) 0.027(2) C11 0.0612(18) 0.075(2) 0.0620(19) -0.0084(16) 0.0060(15) 0.0029(16) S12 0.077(2) 0.112(2) 0.0832(18) -0.0144(16) -0.001(2) -0.025(2) C13 0.072(5) 0.112(5) 0.086(4) -0.029(4) -0.010(4) -0.010(4) C14 0.076(5) 0.115(5) 0.071(3) -0.022(3) -0.008(4) 0.000(4) N15 0.085(5) 0.098(4) 0.058(3) -0.013(3) -0.002(3) -0.006(5) S12B 0.070(4) 0.139(5) 0.087(4) -0.030(4) 0.010(3) -0.046(4) C13B 0.078(6) 0.102(7) 0.078(4) -0.018(5) -0.012(4) -0.010(5) C14B 0.082(6) 0.105(5) 0.066(4) -0.018(4) -0.004(4) -0.009(5) N15B 0.080(7) 0.090(6) 0.056(4) -0.014(4) 0.003(4) -0.011(6) S16 0.0606(5) 0.0889(6) 0.0666(5) 0.0103(4) 0.0110(4) 0.0146(4) C17 0.068(2) 0.0696(19) 0.0425(16) -0.0082(14) -0.0043(14) 0.0089(15) C18 0.080(2) 0.078(2) 0.068(2) -0.0009(18) 0.0054(17) 0.0088(19) C19 0.113(3) 0.074(2) 0.072(2) -0.0020(18) -0.002(2) 0.016(2) C20 0.102(3) 0.075(2) 0.075(2) -0.0189(19) -0.022(2) 0.029(2) C21 0.067(2) 0.099(3) 0.074(2) -0.023(2) -0.0065(18) 0.019(2) C22 0.066(2) 0.083(2) 0.064(2) -0.0053(17) -0.0007(16) 0.0058(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C2 2.016(3) . ? Fe1 C1 2.028(3) . ? Fe1 C6 2.029(3) . ? Fe1 C3 2.034(3) . ? Fe1 C7 2.035(3) . ? Fe1 C8 2.036(3) . ? Fe1 C10 2.040(3) . ? Fe1 C9 2.046(4) . ? Fe1 C5 2.049(3) . ? Fe1 C4 2.056(3) . ? C1 C5 1.424(4) . ? C1 C2 1.445(4) . ? C1 C11 1.467(4) . ? C2 C3 1.422(4) . ? C2 S16 1.752(3) . ? C3 C4 1.406(4) . ? C4 C5 1.414(4) . ? C6 C10 1.404(5) . ? C6 C7 1.415(6) . ? C7 C8 1.387(5) . ? C8 C9 1.390(5) . ? C9 C10 1.402(5) . ? C11 N15 1.282(6) . ? C11 N15B 1.284(7) . ? C11 S12B 1.744(6) . ? C11 S12 1.774(5) . ? S12 C13 1.793(13) . ? C13 C14 1.583(18) . ? C14 N15 1.449(12) . ? S12B C13B 1.83(2) . ? C13B C14B 1.49(2) . ? C14B N15B 1.460(19) . ? S16 C17 1.777(3) . ? C17 C18 1.382(4) . ? C17 C22 1.383(4) . ? C18 C19 1.369(5) . ? C19 C20 1.370(5) . ? C20 C21 1.370(5) . ? C21 C22 1.394(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 C2 Fe1 C1 41.86(11) . . ? C2 Fe1 C6 123.43(15) . . ? C1 Fe1 C6 108.03(14) . . ? C2 Fe1 C3 41.10(12) . . ? C1 Fe1 C3 69.30(12) . . ? C6 Fe1 C3 159.62(17) . . ? C2 Fe1 C7 109.82(14) . . ? C1 Fe1 C7 126.44(16) . . ? C6 Fe1 C7 40.75(16) . . ? C3 Fe1 C7 123.60(15) . . ? C2 Fe1 C8 125.80(14) . . ? C1 Fe1 C8 163.28(16) . . ? C6 Fe1 C8 67.66(16) . . ? C3 Fe1 C8 108.76(14) . . ? C7 Fe1 C8 39.85(15) . . ? C2 Fe1 C10 158.09(15) . . ? C1 Fe1 C10 120.63(14) . . ? C6 Fe1 C10 40.37(14) . . ? C3 Fe1 C10 158.70(16) . . ? C7 Fe1 C10 67.84(16) . . ? C8 Fe1 C10 67.37(15) . . ? C2 Fe1 C9 160.94(14) . . ? C1 Fe1 C9 155.26(14) . . ? C6 Fe1 C9 67.59(16) . . ? C3 Fe1 C9 123.45(14) . . ? C7 Fe1 C9 67.20(16) . . ? C8 Fe1 C9 39.82(14) . . ? C10 Fe1 C9 40.13(14) . . ? C2 Fe1 C5 69.22(12) . . ? C1 Fe1 C5 40.88(11) . . ? C6 Fe1 C5 123.79(15) . . ? C3 Fe1 C5 68.22(13) . . ? C7 Fe1 C5 162.08(17) . . ? C8 Fe1 C5 155.14(16) . . ? C10 Fe1 C5 106.00(14) . . ? C9 Fe1 C5 119.71(15) . . ? C2 Fe1 C4 68.65(12) . . ? C1 Fe1 C4 68.57(12) . . ? C6 Fe1 C4 159.22(17) . . ? C3 Fe1 C4 40.22(13) . . ? C7 Fe1 C4 157.28(16) . . ? C8 Fe1 C4 121.37(16) . . ? C10 Fe1 C4 122.32(16) . . ? C9 Fe1 C4 106.42(15) . . ? C5 Fe1 C4 40.31(12) . . ? C5 C1 C2 107.2(3) . . ? C5 C1 C11 122.6(3) . . ? C2 C1 C11 130.1(3) . . ? C5 C1 Fe1 70.35(16) . . ? C2 C1 Fe1 68.62(16) . . ? C11 C1 Fe1 123.65(19) . . ? C3 C2 C1 107.3(3) . . ? C3 C2 S16 124.2(2) . . ? C1 C2 S16 128.4(2) . . ? C3 C2 Fe1 70.13(17) . . ? C1 C2 Fe1 69.52(16) . . ? S16 C2 Fe1 126.59(15) . . ? C4 C3 C2 108.6(3) . . ? C4 C3 Fe1 70.71(17) . . ? C2 C3 Fe1 68.77(15) . . ? C3 C4 C5 108.6(3) . . ? C3 C4 Fe1 69.08(17) . . ? C5 C4 Fe1 69.60(17) . . ? C4 C5 C1 108.3(3) . . ? C4 C5 Fe1 70.09(18) . . ? C1 C5 Fe1 68.78(16) . . ? C10 C6 C7 107.5(4) . . ? C10 C6 Fe1 70.2(2) . . ? C7 C6 Fe1 69.8(2) . . ? C8 C7 C6 107.7(4) . . ? C8 C7 Fe1 70.1(2) . . ? C6 C7 Fe1 69.4(2) . . ? C7 C8 C9 108.8(4) . . ? C7 C8 Fe1 70.0(2) . . ? C9 C8 Fe1 70.49(19) . . ? C8 C9 C10 108.1(4) . . ? C8 C9 Fe1 69.7(2) . . ? C10 C9 Fe1 69.7(2) . . ? C9 C10 C6 107.8(4) . . ? C9 C10 Fe1 70.1(2) . . ? C6 C10 Fe1 69.4(2) . . ? N15 C11 C1 122.8(7) . . ? N15B C11 C1 115.6(9) . . ? N15 C11 S12B 110.3(7) . . ? N15B C11 S12B 120.9(10) . . ? C1 C11 S12B 123.5(5) . . ? N15 C11 S12 116.1(7) . . ? N15B C11 S12 120.2(10) . . ? C1 C11 S12 121.0(4) . . ? C11 S12 C13 90.4(5) . . ? C14 C13 S12 104.8(7) . . ? N15 C14 C13 107.9(8) . . ? C11 N15 C14 114.4(8) . . ? C11 S12B C13B 88.3(7) . . ? C14B C13B S12B 106.9(11) . . ? N15B C14B C13B 113.1(13) . . ? C11 N15B C14B 109.8(12) . . ? C2 S16 C17 102.70(14) . . ? C18 C17 C22 119.0(3) . . ? C18 C17 S16 116.7(3) . . ? C22 C17 S16 124.3(3) . . ? C19 C18 C17 121.0(3) . . ? C18 C19 C20 120.2(4) . . ? C21 C20 C19 119.8(3) . . ? C20 C21 C22 120.4(4) . . ? C17 C22 C21 119.6(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.423 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 923985' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_5b-PdCl2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 Cl2 Fe N Pd S2, C H Cl3' _chemical_formula_sum 'C15 H16 Cl5 Fe N Pd S2' _chemical_formula_weight 613.91 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.5896(7) _cell_length_b 13.6850(10) _cell_length_c 16.6260(12) _cell_angle_alpha 90.00 _cell_angle_beta 104.2650(10) _cell_angle_gamma 90.00 _cell_volume 2114.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9888 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 25.38 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_min 0.126 _exptl_crystal_size_mid 0.126 _exptl_crystal_size_max 0.214 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.928 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 2.366 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5137 _exptl_absorpt_correction_T_max 0.7833 _exptl_absorpt_process_details '(Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker Smart Apex CCD diffractometer 01-670' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 0.661 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 22995 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.39 _reflns_number_total 3889 _reflns_number_gt 3523 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 7.34A (Bruker, 2006)' _computing_structure_solution 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V 6.12 (Sheldrick, 2000)' _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^)+(0.0300P)^2^+1.3020P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3889 _refine_ls_number_parameters 255 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0650 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.83927(2) 0.512996(15) 0.401533(13) 0.03916(8) Uani 1 1 d . . . Fe1 Fe 0.44562(4) 0.47677(3) 0.28102(3) 0.04536(12) Uani 1 1 d . . . Cl1 Cl 0.95222(9) 0.64088(6) 0.35059(5) 0.0583(2) Uani 1 1 d . . . Cl2 Cl 0.83269(9) 0.60142(6) 0.51787(5) 0.0585(2) Uani 1 1 d . . . S1 S 0.75995(9) 0.33371(6) 0.16332(5) 0.0549(2) Uani 1 1 d . . . S2 S 0.70336(9) 0.39824(6) 0.44590(5) 0.04948(19) Uani 1 1 d . . . N1 N 0.8408(2) 0.43214(16) 0.29937(14) 0.0391(5) Uani 1 1 d . . . C1 C 0.7320(3) 0.38858(18) 0.25258(17) 0.0371(6) Uani 1 1 d . . . C2 C 0.9740(3) 0.4190(3) 0.27111(19) 0.0528(8) Uani 1 1 d . . . H2A H 1.0336 0.3691 0.3043 0.063 Uiso 1 1 calc R . . H2B H 1.0280 0.4796 0.2777 0.063 Uiso 1 1 calc R . . C3 C 0.9354(3) 0.3891(2) 0.1816(2) 0.0514(8) Uani 1 1 d . . . H3A H 1.0051 0.3428 0.1706 0.062 Uiso 1 1 calc R . . H3B H 0.9330 0.4456 0.1460 0.062 Uiso 1 1 calc R . . C4 C 0.5937(3) 0.37495(19) 0.27209(18) 0.0384(6) Uani 1 1 d . . . C5 C 0.4593(3) 0.3514(2) 0.2165(2) 0.0473(7) Uani 1 1 d . . . H5 H 0.4426 0.3451 0.1592 0.057 Uiso 1 1 calc R . . C6 C 0.3564(3) 0.3394(2) 0.2630(2) 0.0505(7) Uani 1 1 d . . . H6 H 0.2601 0.3236 0.2414 0.061 Uiso 1 1 calc R . . C7 C 0.4226(3) 0.3549(2) 0.3475(2) 0.0508(8) Uani 1 1 d . . . H7 H 0.3781 0.3513 0.3911 0.061 Uiso 1 1 calc R . . C8 C 0.5702(3) 0.37735(19) 0.35403(18) 0.0413(6) Uani 1 1 d . . . C9 C 0.5252(5) 0.6109(2) 0.2661(4) 0.0866(15) Uani 1 1 d . . . H9 H 0.6187 0.6238 0.2625 0.104 Uiso 1 1 calc R . . C10 C 0.4083(5) 0.5901(3) 0.1999(3) 0.0829(13) Uani 1 1 d . . . H10 H 0.4101 0.5869 0.1443 0.099 Uiso 1 1 calc R . . C11 C 0.2868(4) 0.5747(3) 0.2317(3) 0.0678(10) Uani 1 1 d . . . H11 H 0.1947 0.5597 0.2007 0.081 Uiso 1 1 calc R . . C12 C 0.3280(4) 0.5856(3) 0.3175(3) 0.0688(10) Uani 1 1 d . . . H12 H 0.2692 0.5788 0.3541 0.083 Uiso 1 1 calc R . . C13 C 0.4771(4) 0.6091(2) 0.3387(3) 0.0819(13) Uani 1 1 d . . . H13 H 0.5330 0.6212 0.3920 0.098 Uiso 1 1 calc R . . C14 C 0.7993(4) 0.2835(2) 0.4556(2) 0.0629(9) Uani 1 1 d . . . H14A H 0.7394 0.2324 0.4682 0.094 Uiso 1 1 calc R . . H14B H 0.8855 0.2883 0.4995 0.094 Uiso 1 1 calc R . . H14C H 0.8240 0.2689 0.4044 0.094 Uiso 1 1 calc R . . C15 C 0.7694(3) 0.6567(3) 0.03564(19) 0.0714(10) Uani 1 1 d D . . H15 H 0.7602 0.7241 0.0151 0.086 Uiso 1 1 calc R A 1 Cl3 Cl 0.8571(10) 0.6565(8) 0.1407(3) 0.107(3) Uani 0.51(2) 1 d PDU B 1 Cl4 Cl 0.5985(9) 0.6051(14) 0.0209(5) 0.128(3) Uani 0.51(2) 1 d PDU B 1 Cl5 Cl 0.8688(10) 0.5891(7) -0.0196(5) 0.123(2) Uani 0.51(2) 1 d PDU B 1 Cl3B Cl 0.8405(8) 0.6536(7) 0.1424(3) 0.0784(19) Uani 0.49(2) 1 d PDU B 2 Cl4B Cl 0.5821(4) 0.6480(9) 0.0121(4) 0.097(2) Uani 0.49(2) 1 d PDU B 2 Cl5B Cl 0.8378(12) 0.5652(9) -0.0155(4) 0.115(3) Uani 0.49(2) 1 d PDU 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 Pd1 0.03988(13) 0.03831(13) 0.04202(14) -0.00633(9) 0.01529(9) -0.00601(9) Fe1 0.0394(2) 0.0355(2) 0.0674(3) 0.00280(19) 0.0249(2) 0.00173(16) Cl1 0.0624(5) 0.0518(4) 0.0607(5) 0.0023(4) 0.0153(4) -0.0198(4) Cl2 0.0641(5) 0.0580(5) 0.0567(5) -0.0212(4) 0.0213(4) -0.0040(4) S1 0.0520(4) 0.0645(5) 0.0534(5) -0.0209(4) 0.0233(4) -0.0074(4) S2 0.0585(5) 0.0510(4) 0.0444(4) -0.0048(3) 0.0230(4) -0.0137(3) N1 0.0381(12) 0.0418(12) 0.0416(13) -0.0049(10) 0.0176(10) -0.0032(10) C1 0.0399(14) 0.0331(13) 0.0402(15) -0.0013(11) 0.0136(12) 0.0031(11) C2 0.0394(15) 0.070(2) 0.0535(19) -0.0077(16) 0.0210(14) -0.0042(14) C3 0.0494(17) 0.0516(17) 0.062(2) -0.0075(15) 0.0296(15) -0.0006(14) C4 0.0378(14) 0.0329(13) 0.0477(16) -0.0009(11) 0.0165(12) 0.0000(11) C5 0.0432(16) 0.0432(16) 0.0549(19) -0.0047(13) 0.0109(13) -0.0003(12) C6 0.0362(15) 0.0410(16) 0.076(2) -0.0002(15) 0.0167(15) -0.0051(12) C7 0.0493(17) 0.0403(16) 0.072(2) 0.0048(15) 0.0326(16) -0.0055(13) C8 0.0436(15) 0.0342(14) 0.0509(17) -0.0003(12) 0.0206(13) -0.0029(11) C9 0.060(2) 0.0339(18) 0.174(5) 0.019(2) 0.044(3) 0.0026(16) C10 0.089(3) 0.059(2) 0.114(4) 0.039(2) 0.050(3) 0.024(2) C11 0.052(2) 0.052(2) 0.102(3) 0.013(2) 0.023(2) 0.0144(15) C12 0.063(2) 0.051(2) 0.100(3) -0.0086(19) 0.034(2) 0.0151(16) C13 0.070(3) 0.0396(19) 0.128(4) -0.020(2) 0.010(3) 0.0085(17) C14 0.068(2) 0.0524(19) 0.060(2) 0.0115(16) -0.0008(17) -0.0091(16) C15 0.087(3) 0.060(2) 0.068(2) -0.0010(18) 0.020(2) 0.0094(19) Cl3 0.134(5) 0.075(4) 0.090(4) -0.001(3) -0.015(3) 0.014(3) Cl4 0.105(3) 0.179(7) 0.105(3) -0.006(4) 0.038(2) -0.038(3) Cl5 0.143(3) 0.140(4) 0.116(4) -0.005(3) 0.088(3) 0.014(3) Cl3B 0.103(3) 0.075(4) 0.054(3) -0.011(2) 0.013(2) 0.030(3) Cl4B 0.080(2) 0.138(5) 0.074(2) -0.023(3) 0.0205(15) 0.002(2) Cl5B 0.149(5) 0.128(4) 0.077(3) 0.001(2) 0.046(3) 0.063(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 Pd1 N1 2.030(2) . ? Pd1 S2 2.2765(8) . ? Pd1 Cl2 2.2956(8) . ? Pd1 Cl1 2.3250(8) . ? Fe1 C8 2.009(3) . ? Fe1 C4 2.021(3) . ? Fe1 C9 2.027(3) . ? Fe1 C10 2.029(4) . ? Fe1 C13 2.036(4) . ? Fe1 C7 2.041(3) . ? Fe1 C11 2.042(3) . ? Fe1 C5 2.045(3) . ? Fe1 C12 2.048(3) . ? Fe1 C6 2.057(3) . ? S1 C1 1.742(3) . ? S1 C3 1.802(3) . ? S2 C8 1.756(3) . ? S2 C14 1.807(4) . ? N1 C1 1.284(3) . ? N1 C2 1.477(3) . ? C1 C4 1.453(4) . ? C2 C3 1.500(4) . ? C4 C5 1.425(4) . ? C4 C8 1.435(4) . ? C5 C6 1.405(4) . ? C6 C7 1.408(5) . ? C7 C8 1.425(4) . ? C9 C10 1.393(6) . ? C9 C13 1.395(6) . ? C10 C11 1.409(5) . ? C11 C12 1.391(5) . ? C12 C13 1.422(5) . ? C15 Cl5B 1.731(5) . ? C15 Cl3B 1.738(5) . ? C15 Cl3 1.741(5) . ? C15 Cl5 1.743(5) . ? C15 Cl4 1.745(5) . ? C15 Cl4B 1.746(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 N1 Pd1 S2 91.02(7) . . ? N1 Pd1 Cl2 178.35(6) . . ? S2 Pd1 Cl2 87.35(3) . . ? N1 Pd1 Cl1 90.31(7) . . ? S2 Pd1 Cl1 173.02(3) . . ? Cl2 Pd1 Cl1 91.27(3) . . ? C8 Fe1 C4 41.72(11) . . ? C8 Fe1 C9 120.11(16) . . ? C4 Fe1 C9 108.85(14) . . ? C8 Fe1 C10 154.25(14) . . ? C4 Fe1 C10 119.35(14) . . ? C9 Fe1 C10 40.19(18) . . ? C8 Fe1 C13 108.70(15) . . ? C4 Fe1 C13 128.50(14) . . ? C9 Fe1 C13 40.16(18) . . ? C10 Fe1 C13 67.4(2) . . ? C8 Fe1 C7 41.19(11) . . ? C4 Fe1 C7 69.40(11) . . ? C9 Fe1 C7 154.17(19) . . ? C10 Fe1 C7 163.58(17) . . ? C13 Fe1 C7 119.63(18) . . ? C8 Fe1 C11 163.78(14) . . ? C4 Fe1 C11 152.98(15) . . ? C9 Fe1 C11 67.82(16) . . ? C10 Fe1 C11 40.51(15) . . ? C13 Fe1 C11 67.34(17) . . ? C7 Fe1 C11 125.71(13) . . ? C8 Fe1 C5 69.10(12) . . ? C4 Fe1 C5 41.04(11) . . ? C9 Fe1 C5 128.38(18) . . ? C10 Fe1 C5 108.42(17) . . ? C13 Fe1 C5 166.40(16) . . ? C7 Fe1 C5 68.18(13) . . ? C11 Fe1 C5 118.55(15) . . ? C8 Fe1 C12 127.03(15) . . ? C4 Fe1 C12 166.24(15) . . ? C9 Fe1 C12 68.23(16) . . ? C10 Fe1 C12 67.75(17) . . ? C13 Fe1 C12 40.75(15) . . ? C7 Fe1 C12 107.02(14) . . ? C11 Fe1 C12 39.75(15) . . ? C5 Fe1 C12 151.25(14) . . ? C8 Fe1 C6 68.47(12) . . ? C4 Fe1 C6 68.49(11) . . ? C9 Fe1 C6 165.0(2) . . ? C10 Fe1 C6 127.08(18) . . ? C13 Fe1 C6 152.82(17) . . ? C7 Fe1 C6 40.19(13) . . ? C11 Fe1 C6 107.41(14) . . ? C5 Fe1 C6 40.06(12) . . ? C12 Fe1 C6 117.93(13) . . ? C1 S1 C3 90.50(13) . . ? C8 S2 C14 100.46(14) . . ? C8 S2 Pd1 100.50(9) . . ? C14 S2 Pd1 108.00(12) . . ? C1 N1 C2 112.8(2) . . ? C1 N1 Pd1 125.98(18) . . ? C2 N1 Pd1 121.19(18) . . ? N1 C1 C4 125.1(2) . . ? N1 C1 S1 116.3(2) . . ? C4 C1 S1 118.4(2) . . ? N1 C2 C3 109.2(2) . . ? C2 C3 S1 105.9(2) . . ? C5 C4 C8 107.0(2) . . ? C5 C4 C1 127.8(3) . . ? C8 C4 C1 125.1(3) . . ? C5 C4 Fe1 70.38(16) . . ? C8 C4 Fe1 68.70(15) . . ? C1 C4 Fe1 128.64(19) . . ? C6 C5 C4 108.4(3) . . ? C6 C5 Fe1 70.44(17) . . ? C4 C5 Fe1 68.58(16) . . ? C5 C6 C7 109.0(3) . . ? C5 C6 Fe1 69.51(17) . . ? C7 C6 Fe1 69.32(17) . . ? C6 C7 C8 107.7(3) . . ? C6 C7 Fe1 70.49(17) . . ? C8 C7 Fe1 68.18(16) . . ? C7 C8 C4 107.9(3) . . ? C7 C8 S2 126.7(2) . . ? C4 C8 S2 125.3(2) . . ? C7 C8 Fe1 70.63(17) . . ? C4 C8 Fe1 69.58(16) . . ? S2 C8 Fe1 127.72(15) . . ? C10 C9 C13 107.9(4) . . ? C10 C9 Fe1 70.0(2) . . ? C13 C9 Fe1 70.3(2) . . ? C9 C10 C11 108.2(4) . . ? C9 C10 Fe1 69.8(2) . . ? C11 C10 Fe1 70.3(2) . . ? C12 C11 C10 108.5(4) . . ? C12 C11 Fe1 70.4(2) . . ? C10 C11 Fe1 69.2(2) . . ? C11 C12 C13 107.0(4) . . ? C11 C12 Fe1 69.9(2) . . ? C13 C12 Fe1 69.18(19) . . ? C9 C13 C12 108.4(4) . . ? C9 C13 Fe1 69.5(2) . . ? C12 C13 Fe1 70.1(2) . . ? Cl3 C15 Cl5 109.6(4) . . ? Cl3 C15 Cl4 110.2(4) . . ? Cl5 C15 Cl4 109.1(4) . . ? Cl5B C15 Cl3B 112.5(3) . . ? Cl5B C15 Cl4B 109.5(4) . . ? Cl3B C15 Cl4B 110.5(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.454 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 923986' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_6b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H23 Fe N S' _chemical_formula_sum 'C16 H23 Fe N S' _chemical_formula_weight 317.26 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 16.558(5) _cell_length_b 8.011(2) _cell_length_c 12.175(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.932(4) _cell_angle_gamma 90.00 _cell_volume 1603.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9418 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 25.31 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_min 0.222 _exptl_crystal_size_mid 0.292 _exptl_crystal_size_max 0.314 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 1.058 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7133 _exptl_absorpt_correction_T_max 0.8171 _exptl_absorpt_process_details '(Sheldrick, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker Smart Apex CCD diffractometer 01-670' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 0.661 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16388 _diffrn_reflns_av_R_equivalents 0.0905 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2925 _reflns_number_gt 2573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0708P)^2^+0.8101P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2925 _refine_ls_number_parameters 222 _refine_ls_number_restraints 236 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1284 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.87023(2) 0.16690(5) 0.11258(3) 0.04815(19) Uani 1 1 d . . . C1 C 0.74865(16) 0.1215(4) 0.0969(2) 0.0439(6) Uani 1 1 d . A . C2 C 0.78985(17) 0.0002(3) 0.0370(2) 0.0458(6) Uani 1 1 d . A . C3 C 0.84763(18) -0.0841(4) 0.1137(3) 0.0526(7) Uani 1 1 d . A . H3 H 0.8848 -0.1726 0.0960 0.063 Uiso 1 1 calc R . . C4 C 0.8428(2) -0.0147(4) 0.2198(3) 0.0576(8) Uani 1 1 d . A . H4 H 0.8760 -0.0469 0.2888 0.069 Uiso 1 1 calc R . . C5 C 0.78191(18) 0.1098(4) 0.2082(3) 0.0524(7) Uani 1 1 d . A . H5 H 0.7662 0.1793 0.2685 0.063 Uiso 1 1 calc R . . C6 C 0.8869(4) 0.4031(10) 0.0569(10) 0.0666(16) Uani 0.672(19) 1 d PDU A 1 H6 H 0.8440 0.4797 0.0259 0.080 Uiso 0.672(19) 1 calc PR A 1 C7 C 0.9280(6) 0.2866(13) -0.0033(5) 0.0677(16) Uani 0.672(19) 1 d PDU A 1 H7 H 0.9185 0.2682 -0.0834 0.081 Uiso 0.672(19) 1 calc PR A 1 C8 C 0.9854(5) 0.2011(11) 0.0717(7) 0.0658(16) Uani 0.672(19) 1 d PDU A 1 H8 H 1.0224 0.1130 0.0529 0.079 Uiso 0.672(19) 1 calc PR A 1 C9 C 0.9786(5) 0.2625(13) 0.1797(5) 0.0636(16) Uani 0.672(19) 1 d PDU A 1 H9 H 1.0106 0.2251 0.2483 0.076 Uiso 0.672(19) 1 calc PR A 1 C10 C 0.9182(6) 0.3884(10) 0.1706(8) 0.0659(17) Uani 0.672(19) 1 d PDU A 1 H10 H 0.9008 0.4535 0.2318 0.079 Uiso 0.672(19) 1 calc PR A 1 C6B C 0.8973(11) 0.4168(18) 0.1328(18) 0.063(2) Uani 0.328(19) 1 d PDU A 2 H6B H 0.8660 0.4991 0.1696 0.075 Uiso 0.328(19) 1 calc PR A 2 C7B C 0.8864(9) 0.376(2) 0.0186(15) 0.064(2) Uani 0.328(19) 1 d PDU A 2 H7B H 0.8458 0.4254 -0.0374 0.076 Uiso 0.328(19) 1 calc PR A 2 C8B C 0.9454(13) 0.256(3) -0.0007(11) 0.066(2) Uani 0.328(19) 1 d PDU A 2 H8B H 0.9522 0.2050 -0.0723 0.080 Uiso 0.328(19) 1 calc PR A 2 C9B C 0.9907(11) 0.216(3) 0.1019(18) 0.066(2) Uani 0.328(19) 1 d PDU A 2 H9B H 1.0354 0.1351 0.1135 0.080 Uiso 0.328(19) 1 calc PR A 2 C10B C 0.9632(12) 0.320(3) 0.1839(9) 0.066(2) Uani 0.328(19) 1 d PDU A 2 H10B H 0.9849 0.3225 0.2624 0.079 Uiso 0.328(19) 1 calc PR A 2 C11 C 0.68133(14) 0.2458(3) 0.0431(2) 0.0383(6) Uani 1 1 d . . . H11A H 0.6823 0.3483 0.0857 0.046 Uiso 1 1 calc R A . H11B H 0.6906 0.2730 -0.0320 0.046 Uiso 1 1 calc R . . N12 N 0.59936(17) 0.1573(3) 0.0434(3) 0.0625(7) Uani 1 1 d . A . C13 C 0.5386(3) 0.2574(7) -0.0249(5) 0.1021(15) Uani 1 1 d . . . H13A H 0.4861 0.2056 -0.0266 0.153 Uiso 1 1 calc R A . H13B H 0.5530 0.2647 -0.0987 0.153 Uiso 1 1 calc R . . H13C H 0.5367 0.3675 0.0059 0.153 Uiso 1 1 calc R . . C14 C 0.5753(3) 0.1366(6) 0.1535(4) 0.0890(13) Uani 1 1 d . . . H14A H 0.5261 0.0721 0.1490 0.133 Uiso 1 1 calc R A . H14B H 0.5662 0.2442 0.1845 0.133 Uiso 1 1 calc R . . H14C H 0.6177 0.0798 0.1998 0.133 Uiso 1 1 calc R . . S15 S 0.77479(6) -0.03090(12) -0.10632(8) 0.0658(3) Uani 1 1 d . . . C16 C 0.6824(2) -0.1503(4) -0.1226(3) 0.0559(8) Uani 1 1 d . A . H16 H 0.6401 -0.0867 -0.0913 0.067 Uiso 1 1 calc R . . C17 C 0.6907(3) -0.3173(5) -0.0673(4) 0.0784(11) Uani 1 1 d . . . H17A H 0.6402 -0.3770 -0.0816 0.118 Uiso 1 1 calc R A . H17B H 0.7041 -0.3025 0.0110 0.118 Uiso 1 1 calc R . . H17C H 0.7330 -0.3797 -0.0960 0.118 Uiso 1 1 calc R . . C18 C 0.6582(3) -0.1690(5) -0.2460(4) 0.0887(13) Uani 1 1 d . . . H18A H 0.6074 -0.2278 -0.2589 0.133 Uiso 1 1 calc R A . H18B H 0.6994 -0.2305 -0.2777 0.133 Uiso 1 1 calc R . . H18C H 0.6523 -0.0606 -0.2796 0.133 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0389(3) 0.0574(3) 0.0484(3) -0.00363(18) 0.00648(19) -0.00450(18) C1 0.0352(13) 0.0467(14) 0.0506(16) -0.0005(12) 0.0087(12) -0.0026(11) C2 0.0394(14) 0.0481(15) 0.0505(16) -0.0017(12) 0.0087(12) -0.0020(12) C3 0.0440(15) 0.0544(17) 0.0598(19) 0.0015(14) 0.0082(14) 0.0048(13) C4 0.0508(17) 0.070(2) 0.0517(18) 0.0105(15) 0.0045(14) 0.0009(15) C5 0.0467(16) 0.0609(18) 0.0515(17) -0.0011(14) 0.0139(14) -0.0033(14) C6 0.064(3) 0.063(3) 0.072(4) 0.003(3) 0.006(3) -0.016(2) C7 0.056(4) 0.084(4) 0.065(2) 0.000(2) 0.017(2) -0.019(3) C8 0.043(3) 0.088(3) 0.069(4) -0.014(3) 0.018(3) -0.017(2) C9 0.045(3) 0.072(4) 0.072(3) -0.019(3) -0.001(2) -0.014(2) C10 0.061(4) 0.063(3) 0.072(3) -0.015(3) 0.004(3) -0.014(3) C6B 0.056(4) 0.064(4) 0.068(5) -0.005(4) 0.007(4) -0.017(3) C7B 0.058(4) 0.072(5) 0.062(4) 0.002(4) 0.013(4) -0.017(3) C8B 0.052(5) 0.084(5) 0.066(4) -0.003(4) 0.018(4) -0.016(4) C9B 0.045(4) 0.085(4) 0.070(4) -0.009(4) 0.010(4) -0.015(3) C10B 0.051(5) 0.075(5) 0.069(3) -0.012(4) 0.003(4) -0.017(4) C11 0.0245(12) 0.0368(13) 0.0535(15) -0.0078(11) 0.0043(11) 0.0025(10) N12 0.0463(15) 0.0589(16) 0.083(2) -0.0033(14) 0.0087(14) 0.0069(12) C13 0.065(3) 0.118(4) 0.121(4) 0.020(3) -0.001(3) 0.021(3) C14 0.068(3) 0.104(3) 0.100(3) 0.012(3) 0.030(2) 0.000(2) S15 0.0627(5) 0.0773(6) 0.0587(5) -0.0056(4) 0.0133(4) -0.0111(4) C16 0.0554(18) 0.0526(17) 0.0607(19) -0.0042(14) 0.0110(15) 0.0060(14) C17 0.095(3) 0.072(2) 0.069(2) 0.0036(18) 0.009(2) -0.012(2) C18 0.101(3) 0.084(3) 0.076(3) 0.004(2) -0.012(2) 0.002(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 C2 2.027(3) . ? Fe1 C5 2.029(3) . ? Fe1 C9 2.030(6) . ? Fe1 C1 2.032(3) . ? Fe1 C10 2.036(7) . ? Fe1 C7 2.038(10) . ? Fe1 C6 2.040(8) . ? Fe1 C4 2.042(3) . ? Fe1 C3 2.046(3) . ? Fe1 C8 2.047(9) . ? Fe1 C9B 2.05(2) . ? Fe1 C6B 2.060(14) . ? C1 C5 1.403(4) . ? C1 C2 1.436(4) . ? C1 C11 1.577(4) . ? C2 C3 1.424(4) . ? C2 S15 1.750(3) . ? C3 C4 1.418(5) . ? C4 C5 1.414(5) . ? C6 C7 1.411(6) . ? C6 C10 1.424(6) . ? C7 C8 1.413(6) . ? C8 C9 1.420(5) . ? C9 C10 1.416(6) . ? C6B C7B 1.418(6) . ? C6B C10B 1.419(6) . ? C7B C8B 1.415(6) . ? C8B C9B 1.414(6) . ? C9B C10B 1.418(6) . ? C11 N12 1.532(4) . ? N12 C14 1.453(5) . ? N12 C13 1.465(5) . ? S15 C16 1.794(4) . ? C16 C17 1.497(5) . ? C16 C18 1.515(6) . ? 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 C2 Fe1 C5 68.47(12) . . ? C2 Fe1 C9 158.7(3) . . ? C5 Fe1 C9 121.2(2) . . ? C2 Fe1 C1 41.44(11) . . ? C5 Fe1 C1 40.44(12) . . ? C9 Fe1 C1 157.4(3) . . ? C2 Fe1 C10 160.0(4) . . ? C5 Fe1 C10 106.0(2) . . ? C9 Fe1 C10 40.77(17) . . ? C1 Fe1 C10 122.0(3) . . ? C2 Fe1 C7 109.5(2) . . ? C5 Fe1 C7 159.2(3) . . ? C9 Fe1 C7 68.6(3) . . ? C1 Fe1 C7 124.2(3) . . ? C10 Fe1 C7 68.5(3) . . ? C2 Fe1 C6 124.6(3) . . ? C5 Fe1 C6 122.4(3) . . ? C9 Fe1 C6 68.6(2) . . ? C1 Fe1 C6 107.9(2) . . ? C10 Fe1 C6 40.90(18) . . ? C7 Fe1 C6 40.5(2) . . ? C2 Fe1 C4 68.70(13) . . ? C5 Fe1 C4 40.64(13) . . ? C9 Fe1 C4 105.4(2) . . ? C1 Fe1 C4 68.81(12) . . ? C10 Fe1 C4 120.4(3) . . ? C7 Fe1 C4 159.6(3) . . ? C6 Fe1 C4 157.3(4) . . ? C2 Fe1 C3 40.94(12) . . ? C5 Fe1 C3 68.26(13) . . ? C9 Fe1 C3 121.4(3) . . ? C1 Fe1 C3 69.18(12) . . ? C10 Fe1 C3 156.7(4) . . ? C7 Fe1 C3 124.7(3) . . ? C6 Fe1 C3 161.1(4) . . ? C4 Fe1 C3 40.59(13) . . ? C2 Fe1 C8 123.9(3) . . ? C5 Fe1 C8 158.0(3) . . ? C9 Fe1 C8 40.77(19) . . ? C1 Fe1 C8 160.5(3) . . ? C10 Fe1 C8 68.4(3) . . ? C7 Fe1 C8 40.5(2) . . ? C6 Fe1 C8 68.1(3) . . ? C4 Fe1 C8 122.4(2) . . ? C3 Fe1 C8 108.0(2) . . ? C2 Fe1 C9B 133.4(6) . . ? C5 Fe1 C9B 148.5(6) . . ? C9 Fe1 C9B 30.1(5) . . ? C1 Fe1 C9B 171.0(6) . . ? C10 Fe1 C9B 60.9(5) . . ? C7 Fe1 C9B 47.5(6) . . ? C6 Fe1 C9B 68.3(6) . . ? C4 Fe1 C9B 118.0(5) . . ? C3 Fe1 C9B 111.6(5) . . ? C8 Fe1 C9B 10.8(5) . . ? C2 Fe1 C6B 144.7(6) . . ? C5 Fe1 C6B 108.2(4) . . ? C9 Fe1 C6B 54.3(4) . . ? C1 Fe1 C6B 112.6(5) . . ? C10 Fe1 C6B 16.5(4) . . ? C7 Fe1 C6B 60.8(4) . . ? C6 Fe1 C6B 26.1(4) . . ? C4 Fe1 C6B 132.7(6) . . ? C3 Fe1 C6B 172.7(7) . . ? C8 Fe1 C6B 72.7(4) . . ? C9B Fe1 C6B 67.8(5) . . ? C5 C1 C2 106.9(3) . . ? C5 C1 C11 128.2(3) . . ? C2 C1 C11 124.9(3) . . ? C5 C1 Fe1 69.66(16) . . ? C2 C1 Fe1 69.08(15) . . ? C11 C1 Fe1 124.65(18) . . ? C3 C2 C1 108.1(3) . . ? C3 C2 S15 126.2(2) . . ? C1 C2 S15 125.7(2) . . ? C3 C2 Fe1 70.25(18) . . ? C1 C2 Fe1 69.48(16) . . ? S15 C2 Fe1 123.61(15) . . ? C4 C3 C2 107.8(3) . . ? C4 C3 Fe1 69.57(19) . . ? C2 C3 Fe1 68.81(17) . . ? C5 C4 C3 107.7(3) . . ? C5 C4 Fe1 69.17(18) . . ? C3 C4 Fe1 69.84(18) . . ? C1 C5 C4 109.6(3) . . ? C1 C5 Fe1 69.90(16) . . ? C4 C5 Fe1 70.19(17) . . ? C7 C6 C10 108.0(3) . . ? C7 C6 Fe1 69.7(5) . . ? C10 C6 Fe1 69.4(4) . . ? C6 C7 C8 108.3(3) . . ? C6 C7 Fe1 69.9(4) . . ? C8 C7 Fe1 70.1(5) . . ? C7 C8 C9 108.0(3) . . ? C7 C8 Fe1 69.4(5) . . ? C9 C8 Fe1 69.0(4) . . ? C10 C9 C8 108.0(3) . . ? C10 C9 Fe1 69.8(4) . . ? C8 C9 Fe1 70.3(4) . . ? C9 C10 C6 107.7(3) . . ? C9 C10 Fe1 69.4(4) . . ? C6 C10 Fe1 69.7(4) . . ? C7B C6B C10B 107.8(4) . . ? C7B C6B Fe1 70.1(9) . . ? C10B C6B Fe1 70.5(8) . . ? C8B C7B C6B 108.1(4) . . ? C8B C7B Fe1 71.1(10) . . ? C6B C7B Fe1 69.7(8) . . ? C9B C8B C7B 108.1(4) . . ? C9B C8B Fe1 68.6(12) . . ? C7B C8B Fe1 69.1(10) . . ? C8B C9B C10B 108.0(4) . . ? C8B C9B Fe1 71.5(12) . . ? C10B C9B Fe1 70.7(9) . . ? C9B C10B C6B 108.0(4) . . ? C9B C10B Fe1 69.1(10) . . ? C6B C10B Fe1 69.4(8) . . ? N12 C11 C1 106.8(2) . . ? C14 N12 C13 109.9(3) . . ? C14 N12 C11 113.4(3) . . ? C13 N12 C11 107.1(3) . . ? C2 S15 C16 101.71(15) . . ? C17 C16 C18 110.9(3) . . ? C17 C16 S15 113.3(3) . . ? C18 C16 S15 106.4(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.591 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.070 #==end _database_code_depnum_ccdc_archive 'CCDC 923987'