data_publication_text _publ_requested_journal J.Am.Chem.Soc. _publ_contact_author_name 'David P. Goldberg' _publ_contact_author_address ;Department of Chemistry Johns Hopkins University 3400 N. Charles Street Baltimore, MD, 21218 USA ; _publ_contact_author_email dpg@jhu.edu loop_ _publ_author_name _publ_author_address 'Badiei, Yosra' ;Department of Chemistry Johns Hopkins University 3400 N. Charles Street Baltimore, MD, 21218 USA ; 'Siegler, Maxime A.' ;Department of Chemistry Johns Hopkins University 3400 N. Charles Street Baltimore, MD, 21218 USA ; 'Goldberg, David P.' ;Department of Chemistry Johns Hopkins University 3400 N. Charles Street Baltimore, MD, 21218 USA ; data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H48 Cl Fe N3 S, C H2 Cl2' _chemical_formula_sum 'C40 H50 Cl3 Fe N3 S' _chemical_formula_weight 767.09 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' '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' '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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 41' _symmetry_space_group_name_Hall 'P 4w' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z+1/4' '-x, -y, z+1/2' 'y, -x, z+3/4' _cell_length_a 12.73727(14) _cell_length_b 12.73727(14) _cell_length_c 25.1972(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4087.94(9) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 14311 _cell_measurement_theta_min 1.60 _cell_measurement_theta_max 26.31 _exptl_crystal_description 'octahedron' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.646 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.859 _exptl_absorpt_correction_T_max 0.904 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 15.9890 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23227 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7190 _reflns_number_gt 6240 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'DIRDIF08 (Beurskens et al., 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL v6.10 (Sheldrick, 2008)' _computing_publication_material 'SHELXTL v6.10 (Sheldrick, 2008)' _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^)+(0.0588P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.002(14) _refine_ls_number_reflns 7190 _refine_ls_number_parameters 498 _refine_ls_number_restraints 184 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.006 _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 0.14031(3) 0.37250(3) 0.257934(16) 0.01461(11) Uani 1 1 d . . . Cl1 Cl 0.13499(6) 0.50178(7) 0.19679(3) 0.0272(2) Uani 1 1 d . A . C1 C -0.0575(2) 0.2917(2) 0.30962(12) 0.0182(7) Uani 1 1 d . . . C2 C 0.2957(2) 0.3684(2) 0.34675(12) 0.0162(6) Uani 1 1 d . . . C3 C -0.1639(3) 0.2511(3) 0.32148(14) 0.0302(8) Uani 1 1 d . A . H3A H -0.2131 0.2755 0.2942 0.045 Uiso 1 1 calc R . . H3B H -0.1866 0.2769 0.3563 0.045 Uiso 1 1 calc R . . H3C H -0.1625 0.1742 0.3218 0.045 Uiso 1 1 calc R . . C4 C 0.3927(3) 0.3716(3) 0.37930(13) 0.0236(8) Uani 1 1 d . A . H4A H 0.4265 0.3025 0.3787 0.035 Uiso 1 1 calc R . . H4B H 0.3748 0.3902 0.4159 0.035 Uiso 1 1 calc R . . H4C H 0.4409 0.4242 0.3648 0.035 Uiso 1 1 calc R . . C5 C 0.0288(2) 0.2715(2) 0.34806(12) 0.0166(7) Uani 1 1 d . A . C6 C 0.0188(3) 0.2180(2) 0.39523(13) 0.0206(7) Uani 1 1 d . . . H6 H -0.0472 0.1898 0.4056 0.025 Uiso 1 1 calc R A . C7 C 0.1066(3) 0.2057(3) 0.42752(13) 0.0239(8) Uani 1 1 d . A . H7 H 0.1021 0.1667 0.4596 0.029 Uiso 1 1 calc R . . C8 C 0.2009(3) 0.2512(3) 0.41224(13) 0.0222(7) Uani 1 1 d . . . H8 H 0.2618 0.2444 0.4338 0.027 Uiso 1 1 calc R A . C9 C 0.2046(2) 0.3065(2) 0.36511(11) 0.0148(7) Uani 1 1 d . A . C10 C -0.1056(2) 0.3721(3) 0.22790(12) 0.0213(7) Uani 1 1 d . . . C11 C -0.1438(2) 0.4754(3) 0.22823(14) 0.0272(8) Uani 1 1 d . A . C12 C -0.2131(3) 0.5040(3) 0.18842(16) 0.0375(10) Uani 1 1 d . . . H12 H -0.2399 0.5736 0.1879 0.045 Uiso 1 1 calc R A . C13 C -0.2442(3) 0.4352(4) 0.14974(16) 0.0434(11) Uani 1 1 d . A . H13 H -0.2929 0.4565 0.1233 0.052 Uiso 1 1 calc R . . C14 C -0.2043(3) 0.3352(4) 0.14946(15) 0.0425(11) Uani 1 1 d . . . H14 H -0.2246 0.2883 0.1220 0.051 Uiso 1 1 calc R A . C15 C -0.1344(3) 0.3003(3) 0.18852(14) 0.0304(8) Uani 1 1 d . A . C16 C -0.1151(3) 0.5522(3) 0.27231(14) 0.0301(9) Uani 1 1 d . . . H16 H -0.0462 0.5298 0.2876 0.036 Uiso 1 1 calc R A . C17 C -0.1961(3) 0.5493(3) 0.31641(17) 0.0456(11) Uani 1 1 d . A . H17A H -0.1722 0.5930 0.3461 0.068 Uiso 1 1 calc R . . H17B H -0.2053 0.4768 0.3286 0.068 Uiso 1 1 calc R . . H17C H -0.2632 0.5763 0.3031 0.068 Uiso 1 1 calc R . . C18 C -0.1029(3) 0.6653(3) 0.2520(2) 0.0531(12) Uani 1 1 d . A . H18A H -0.1710 0.6912 0.2395 0.080 Uiso 1 1 calc R . . H18B H -0.0524 0.6666 0.2227 0.080 Uiso 1 1 calc R . . H18C H -0.0775 0.7102 0.2809 0.080 Uiso 1 1 calc R . . C19 C -0.0910(3) 0.1914(3) 0.18484(17) 0.0463(11) Uani 1 1 d . . . H19 H -0.0404 0.1820 0.2148 0.056 Uiso 1 1 calc R A . C20 C -0.1769(4) 0.1070(4) 0.1907(2) 0.0620(14) Uani 1 1 d . A . H20A H -0.2123 0.1156 0.2250 0.093 Uiso 1 1 calc R . . H20B H -0.1450 0.0371 0.1889 0.093 Uiso 1 1 calc R . . H20C H -0.2282 0.1147 0.1620 0.093 Uiso 1 1 calc R . . C21 C -0.0297(4) 0.1760(4) 0.1329(2) 0.0638(15) Uani 1 1 d . A . H21A H -0.0780 0.1809 0.1028 0.096 Uiso 1 1 calc R . . H21B H 0.0038 0.1068 0.1331 0.096 Uiso 1 1 calc R . . H21C H 0.0242 0.2306 0.1299 0.096 Uiso 1 1 calc R . . C22 C 0.3538(2) 0.4973(2) 0.28642(11) 0.0155(7) Uani 1 1 d . . . C23 C 0.3283(2) 0.6022(3) 0.29736(12) 0.0197(7) Uani 1 1 d . A . C24 C 0.4014(3) 0.6791(3) 0.28416(13) 0.0233(7) Uani 1 1 d . . . H24 H 0.3865 0.7507 0.2915 0.028 Uiso 1 1 calc R A . C25 C 0.4960(3) 0.6521(3) 0.26034(14) 0.0247(7) Uani 1 1 d . A . H25 H 0.5466 0.7048 0.2527 0.030 Uiso 1 1 calc R . . C26 C 0.5163(2) 0.5489(3) 0.24789(12) 0.0233(8) Uani 1 1 d . . . H26 H 0.5804 0.5319 0.2307 0.028 Uiso 1 1 calc R A . C27 C 0.4465(2) 0.4689(2) 0.25957(13) 0.0193(7) Uani 1 1 d . A . C28 C 0.2272(3) 0.6309(3) 0.32611(13) 0.0231(7) Uani 1 1 d . . . H28 H 0.1812 0.5672 0.3260 0.028 Uiso 1 1 calc R A . C29 C 0.1667(3) 0.7190(3) 0.29867(15) 0.0326(8) Uani 1 1 d . A . H29A H 0.2121 0.7806 0.2950 0.049 Uiso 1 1 calc R . . H29B H 0.1049 0.7374 0.3199 0.049 Uiso 1 1 calc R . . H29C H 0.1441 0.6954 0.2634 0.049 Uiso 1 1 calc R . . C30 C 0.2482(3) 0.6592(3) 0.38349(14) 0.0372(9) Uani 1 1 d . A . H30A H 0.2860 0.6016 0.4008 0.056 Uiso 1 1 calc R . . H30B H 0.1814 0.6711 0.4018 0.056 Uiso 1 1 calc R . . H30C H 0.2908 0.7232 0.3850 0.056 Uiso 1 1 calc R . . C31 C 0.4690(2) 0.3574(3) 0.24364(13) 0.0222(8) Uani 1 1 d . . . H31 H 0.4135 0.3122 0.2600 0.027 Uiso 1 1 calc R A . C32 C 0.5764(3) 0.3173(3) 0.26387(16) 0.0332(9) Uani 1 1 d . A . H32A H 0.6327 0.3594 0.2481 0.050 Uiso 1 1 calc R . . H32B H 0.5853 0.2436 0.2537 0.050 Uiso 1 1 calc R . . H32C H 0.5792 0.3235 0.3026 0.050 Uiso 1 1 calc R . . C33 C 0.4610(3) 0.3446(3) 0.18379(14) 0.0308(9) Uani 1 1 d . A . H33A H 0.3906 0.3649 0.1720 0.046 Uiso 1 1 calc R . . H33B H 0.4741 0.2711 0.1743 0.046 Uiso 1 1 calc R . . H33C H 0.5133 0.3895 0.1665 0.046 Uiso 1 1 calc R . . S1 S 0.20455(7) 0.21647(7) 0.22217(3) 0.02331(19) Uani 0.62(2) 1 d PDU A 1 C34 C 0.2218(14) 0.124(3) 0.2735(12) 0.0300(18) Uani 0.62(2) 1 d PDU A 1 C35 C 0.1387(11) 0.0651(12) 0.2934(5) 0.032(2) Uani 0.62(2) 1 d PDU A 1 H35 H 0.0706 0.0739 0.2787 0.039 Uiso 0.62(2) 1 calc PR A 1 C36 C 0.1531(10) -0.0054(9) 0.3336(4) 0.035(2) Uani 0.62(2) 1 d PDU A 1 H36 H 0.0943 -0.0436 0.3465 0.042 Uiso 0.62(2) 1 calc PR A 1 C37 C 0.2478(11) -0.0227(7) 0.3557(3) 0.034(2) Uani 0.62(2) 1 d PDU A 1 H37 H 0.2565 -0.0719 0.3837 0.041 Uiso 0.62(2) 1 calc PR A 1 C38 C 0.3359(10) 0.0370(8) 0.3352(4) 0.039(2) Uani 0.62(2) 1 d PDU A 1 H38 H 0.4037 0.0274 0.3502 0.047 Uiso 0.62(2) 1 calc PR A 1 C39 C 0.3226(9) 0.1076(9) 0.2942(4) 0.034(2) Uani 0.62(2) 1 d PDU A 1 H39 H 0.3811 0.1446 0.2801 0.041 Uiso 0.62(2) 1 calc PR A 1 S1' S 0.20455(7) 0.21647(7) 0.22217(3) 0.02331(19) Uani 0.38(2) 1 d PDU A 2 C34' C 0.211(2) 0.122(4) 0.274(2) 0.032(2) Uani 0.38(2) 1 d PDU A 2 C35' C 0.1217(17) 0.062(2) 0.2852(9) 0.034(2) Uani 0.38(2) 1 d PDU A 2 H35' H 0.0605 0.0716 0.2642 0.040 Uiso 0.38(2) 1 calc PR A 2 C36' C 0.1205(15) -0.0102(15) 0.3252(7) 0.039(3) Uani 0.38(2) 1 d PDU A 2 H36' H 0.0600 -0.0532 0.3289 0.047 Uiso 0.38(2) 1 calc PR A 2 C37' C 0.2000(18) -0.0242(13) 0.3597(7) 0.045(3) Uani 0.38(2) 1 d PDU A 2 H37' H 0.1926 -0.0669 0.3904 0.054 Uiso 0.38(2) 1 calc PR A 2 C38' C 0.2980(15) 0.0294(14) 0.3476(7) 0.042(3) Uani 0.38(2) 1 d PDU A 2 H38' H 0.3600 0.0138 0.3669 0.050 Uiso 0.38(2) 1 calc PR A 2 C39' C 0.2995(14) 0.1051(15) 0.3066(7) 0.035(3) Uani 0.38(2) 1 d PDU A 2 H39' H 0.3614 0.1451 0.3008 0.042 Uiso 0.38(2) 1 calc PR A 2 N1 N -0.02983(19) 0.34384(19) 0.26794(9) 0.0169(6) Uani 1 1 d . A . N2 N 0.12114(19) 0.31392(19) 0.33324(10) 0.0143(5) Uani 1 1 d . A . N3 N 0.27962(19) 0.42010(19) 0.30302(9) 0.0145(5) Uani 1 1 d . A . C1S C 0.0606(4) 0.4807(4) 0.4694(2) 0.0680(14) Uani 1 1 d . . . H1S1 H 0.1339 0.4703 0.4575 0.082 Uiso 1 1 calc R . . H1S2 H 0.0354 0.4133 0.4843 0.082 Uiso 1 1 calc R . . Cl2 Cl 0.05840(12) 0.57719(14) 0.51967(6) 0.0909(5) Uani 1 1 d . . . Cl3 Cl -0.01671(12) 0.51423(11) 0.41508(6) 0.0770(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0135(2) 0.0188(2) 0.0115(2) 0.00128(19) -0.00013(18) 0.00049(19) Cl1 0.0245(4) 0.0338(5) 0.0234(4) 0.0137(4) -0.0018(3) -0.0022(4) C1 0.0172(17) 0.0190(17) 0.0182(17) -0.0017(13) 0.0016(13) 0.0048(13) C2 0.0199(17) 0.0158(16) 0.0128(15) -0.0027(12) 0.0012(13) 0.0024(13) C3 0.0207(18) 0.043(2) 0.0267(19) 0.0086(16) 0.0026(15) -0.0001(16) C4 0.0215(18) 0.0297(19) 0.0197(17) 0.0033(14) -0.0025(14) -0.0038(15) C5 0.0173(17) 0.0164(16) 0.0162(16) -0.0010(13) 0.0033(13) 0.0015(13) C6 0.0180(17) 0.0206(18) 0.0232(17) 0.0014(14) 0.0017(13) -0.0004(14) C7 0.030(2) 0.0271(18) 0.0148(16) 0.0068(14) 0.0000(14) 0.0024(16) C8 0.0211(18) 0.0238(18) 0.0217(17) 0.0031(14) -0.0046(14) -0.0001(15) C9 0.0186(16) 0.0151(16) 0.0109(15) -0.0004(12) -0.0018(12) 0.0020(13) C10 0.0088(15) 0.037(2) 0.0179(17) 0.0070(15) 0.0025(13) -0.0011(14) C11 0.0139(17) 0.038(2) 0.029(2) 0.0163(16) 0.0064(15) 0.0029(15) C12 0.0228(19) 0.054(3) 0.036(2) 0.027(2) 0.0044(17) 0.0076(18) C13 0.020(2) 0.082(3) 0.028(2) 0.025(2) -0.0007(16) 0.008(2) C14 0.020(2) 0.087(4) 0.021(2) 0.000(2) -0.0044(15) -0.006(2) C15 0.0162(17) 0.049(2) 0.026(2) -0.0021(17) 0.0033(15) 0.0040(17) C16 0.0229(18) 0.031(2) 0.037(2) 0.0102(16) 0.0000(15) 0.0083(16) C17 0.044(2) 0.049(3) 0.044(3) -0.004(2) 0.006(2) 0.004(2) C18 0.047(3) 0.037(2) 0.076(3) 0.010(2) 0.000(3) 0.0086(19) C19 0.030(2) 0.064(3) 0.045(3) -0.019(2) -0.0205(19) 0.008(2) C20 0.057(3) 0.053(3) 0.075(4) -0.012(3) -0.017(3) -0.001(2) C21 0.040(3) 0.096(4) 0.056(3) -0.038(3) -0.008(2) 0.014(3) C22 0.0153(16) 0.0199(17) 0.0112(15) 0.0042(13) -0.0052(12) -0.0008(13) C23 0.0233(17) 0.0233(18) 0.0126(15) -0.0015(13) -0.0050(13) -0.0018(14) C24 0.0294(19) 0.0215(18) 0.0190(17) 0.0025(14) -0.0058(14) -0.0039(15) C25 0.0275(18) 0.0272(18) 0.0193(17) 0.0038(15) -0.0011(15) -0.0112(14) C26 0.0166(16) 0.036(2) 0.0171(17) 0.0058(14) -0.0011(13) -0.0031(15) C27 0.0144(15) 0.0264(17) 0.0172(15) 0.0002(15) -0.0055(14) 0.0016(13) C28 0.0228(18) 0.0194(18) 0.0273(18) 0.0004(14) -0.0005(14) -0.0009(14) C29 0.034(2) 0.034(2) 0.030(2) -0.0005(17) -0.0010(17) 0.0059(17) C30 0.034(2) 0.054(3) 0.0235(19) -0.0019(18) 0.0013(16) 0.0064(19) C31 0.0145(16) 0.0269(19) 0.0253(19) 0.0022(14) 0.0044(13) 0.0035(14) C32 0.0232(18) 0.038(2) 0.038(2) 0.0047(18) 0.0025(17) 0.0080(16) C33 0.036(2) 0.032(2) 0.0238(19) -0.0045(16) 0.0021(16) 0.0042(17) S1 0.0262(5) 0.0246(5) 0.0191(4) -0.0074(4) -0.0005(4) 0.0021(4) C34 0.038(4) 0.027(3) 0.025(3) -0.010(3) -0.007(4) 0.008(4) C35 0.043(4) 0.028(3) 0.026(4) -0.009(3) -0.001(3) 0.008(3) C36 0.046(5) 0.029(3) 0.030(4) 0.001(3) -0.009(4) 0.007(4) C37 0.052(6) 0.023(3) 0.028(3) -0.002(3) -0.005(4) 0.013(4) C38 0.046(5) 0.032(3) 0.038(4) -0.007(3) -0.011(4) 0.013(4) C39 0.043(4) 0.031(3) 0.030(4) -0.003(3) -0.005(3) 0.003(3) S1' 0.0262(5) 0.0246(5) 0.0191(4) -0.0074(4) -0.0005(4) 0.0021(4) C34' 0.041(5) 0.028(4) 0.027(4) -0.008(4) -0.008(4) 0.009(4) C35' 0.044(5) 0.029(4) 0.028(5) -0.004(4) -0.005(4) 0.012(4) C36' 0.049(6) 0.031(4) 0.036(5) -0.002(4) -0.008(5) 0.012(5) C37' 0.052(7) 0.035(4) 0.047(5) -0.005(4) -0.017(5) 0.011(5) C38' 0.048(6) 0.038(5) 0.039(5) -0.008(4) -0.013(5) 0.008(5) C39' 0.043(5) 0.029(4) 0.033(5) -0.006(4) -0.009(4) 0.003(4) N1 0.0137(13) 0.0212(14) 0.0159(15) 0.0016(11) -0.0006(10) 0.0034(11) N2 0.0145(13) 0.0134(13) 0.0150(13) -0.0013(10) 0.0039(10) 0.0007(11) N3 0.0166(13) 0.0154(13) 0.0117(13) -0.0006(11) -0.0015(10) 0.0022(11) C1S 0.062(3) 0.072(3) 0.070(3) -0.014(3) 0.000(3) 0.008(3) Cl2 0.0818(10) 0.1101(12) 0.0809(11) -0.0387(9) -0.0153(8) 0.0210(9) Cl3 0.0838(10) 0.0741(9) 0.0730(9) -0.0128(7) -0.0188(8) 0.0112(8) _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 N2 2.054(2) . ? Fe1 N3 2.192(2) . ? Fe1 N1 2.212(2) . ? Fe1 Cl1 2.2560(9) . ? Fe1 S1 2.3305(9) . ? C1 N1 1.292(4) . ? C1 C3 1.481(5) . ? C1 C5 1.488(4) . ? C2 N3 1.300(4) . ? C2 C9 1.478(4) . ? C2 C4 1.484(4) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N2 1.347(4) . ? C5 C6 1.376(4) . ? C6 C7 1.393(4) . ? C6 H6 0.9500 . ? C7 C8 1.388(5) . ? C7 H7 0.9500 . ? C8 C9 1.382(4) . ? C8 H8 0.9500 . ? C9 N2 1.335(4) . ? C10 C15 1.398(5) . ? C10 C11 1.402(5) . ? C10 N1 1.442(4) . ? C11 C12 1.385(5) . ? C11 C16 1.525(5) . ? C12 C13 1.369(6) . ? C12 H12 0.9500 . ? C13 C14 1.372(6) . ? C13 H13 0.9500 . ? C14 C15 1.400(5) . ? C14 H14 0.9500 . ? C15 C19 1.496(6) . ? C16 C17 1.517(5) . ? C16 C18 1.536(5) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C21 1.535(6) . ? C19 C20 1.542(6) . ? C19 H19 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.402(4) . ? C22 C27 1.408(4) . ? C22 N3 1.426(4) . ? C23 C24 1.391(5) . ? C23 C28 1.523(5) . ? C24 C25 1.389(5) . ? C24 H24 0.9500 . ? C25 C26 1.376(5) . ? C25 H25 0.9500 . ? C26 C27 1.384(4) . ? C26 H26 0.9500 . ? C27 C31 1.504(5) . ? C28 C30 1.514(5) . ? C28 C29 1.526(5) . ? C28 H28 1.0000 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C33 1.520(5) . ? C31 C32 1.547(4) . ? C31 H31 1.0000 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? S1 C34 1.761(8) . ? C34 C35 1.392(9) . ? C34 C39 1.402(10) . ? C35 C36 1.368(9) . ? C35 H35 0.9500 . ? C36 C37 1.345(10) . ? C36 H36 0.9500 . ? C37 C38 1.452(10) . ? C37 H37 0.9500 . ? C38 C39 1.381(9) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C34' C39' 1.402(13) . ? C34' C35' 1.403(13) . ? C35' C36' 1.364(13) . ? C35' H35' 0.9500 . ? C36' C37' 1.348(14) . ? C36' H36' 0.9500 . ? C37' C38' 1.455(15) . ? C37' H37' 0.9500 . ? C38' C39' 1.412(14) . ? C38' H38' 0.9500 . ? C39' H39' 0.9500 . ? C1S Cl3 1.740(6) . ? C1S Cl2 1.765(5) . ? C1S H1S1 0.9900 . ? C1S H1S2 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Fe1 N3 73.62(9) . . ? N2 Fe1 N1 73.64(9) . . ? N3 Fe1 N1 141.21(9) . . ? N2 Fe1 Cl1 153.21(7) . . ? N3 Fe1 Cl1 100.15(7) . . ? N1 Fe1 Cl1 99.72(7) . . ? N2 Fe1 S1 95.11(7) . . ? N3 Fe1 S1 98.74(7) . . ? N1 Fe1 S1 104.32(7) . . ? Cl1 Fe1 S1 111.65(4) . . ? N1 C1 C3 126.4(3) . . ? N1 C1 C5 114.6(3) . . ? C3 C1 C5 119.0(3) . . ? N3 C2 C9 114.3(3) . . ? N3 C2 C4 125.9(3) . . ? C9 C2 C4 119.7(3) . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 C6 121.3(3) . . ? N2 C5 C1 113.3(3) . . ? C6 C5 C1 125.4(3) . . ? C5 C6 C7 119.0(3) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C8 C7 C6 119.1(3) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C9 C8 C7 118.7(3) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? N2 C9 C8 121.8(3) . . ? N2 C9 C2 113.5(3) . . ? C8 C9 C2 124.6(3) . . ? C15 C10 C11 121.8(3) . . ? C15 C10 N1 120.5(3) . . ? C11 C10 N1 117.6(3) . . ? C12 C11 C10 117.7(4) . . ? C12 C11 C16 120.8(3) . . ? C10 C11 C16 121.5(3) . . ? C13 C12 C11 122.1(4) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C14 119.4(3) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C13 C14 C15 121.8(4) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C10 C15 C14 117.3(4) . . ? C10 C15 C19 123.6(3) . . ? C14 C15 C19 119.0(3) . . ? C17 C16 C11 110.8(3) . . ? C17 C16 C18 109.6(3) . . ? C11 C16 C18 112.6(3) . . ? C17 C16 H16 107.9 . . ? C11 C16 H16 107.9 . . ? C18 C16 H16 107.9 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 C19 C21 111.0(4) . . ? C15 C19 C20 112.2(3) . . ? C21 C19 C20 110.7(4) . . ? C15 C19 H19 107.6 . . ? C21 C19 H19 107.6 . . ? C20 C19 H19 107.6 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C27 122.2(3) . . ? C23 C22 N3 116.5(3) . . ? C27 C22 N3 121.3(3) . . ? C24 C23 C22 118.0(3) . . ? C24 C23 C28 120.7(3) . . ? C22 C23 C28 121.2(3) . . ? C25 C24 C23 120.6(3) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C26 C25 C24 119.8(3) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C25 C26 C27 122.3(3) . . ? C25 C26 H26 118.9 . . ? C27 C26 H26 118.9 . . ? C26 C27 C22 116.9(3) . . ? C26 C27 C31 121.1(3) . . ? C22 C27 C31 122.0(3) . . ? C30 C28 C23 111.2(3) . . ? C30 C28 C29 110.3(3) . . ? C23 C28 C29 112.9(3) . . ? C30 C28 H28 107.4 . . ? C23 C28 H28 107.4 . . ? C29 C28 H28 107.4 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C27 C31 C33 110.7(3) . . ? C27 C31 C32 113.1(3) . . ? C33 C31 C32 110.5(3) . . ? C27 C31 H31 107.4 . . ? C33 C31 H31 107.4 . . ? C32 C31 H31 107.4 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C34 S1 Fe1 109.2(15) . . ? C35 C34 C39 118.7(7) . . ? C35 C34 S1 122.1(8) . . ? C39 C34 S1 119.2(8) . . ? C36 C35 C34 121.4(8) . . ? C36 C35 H35 119.3 . . ? C34 C35 H35 119.3 . . ? C37 C36 C35 122.3(8) . . ? C37 C36 H36 118.9 . . ? C35 C36 H36 118.9 . . ? C36 C37 C38 117.4(7) . . ? C36 C37 H37 121.3 . . ? C38 C37 H37 121.3 . . ? C39 C38 C37 120.9(7) . . ? C39 C38 H38 119.6 . . ? C37 C38 H38 119.6 . . ? C38 C39 C34 119.3(8) . . ? C38 C39 H39 120.4 . . ? C34 C39 H39 120.4 . . ? C39' C34' C35' 117.0(11) . . ? C36' C35' C34' 121.4(13) . . ? C36' C35' H35' 119.3 . . ? C34' C35' H35' 119.3 . . ? C37' C36' C35' 123.9(13) . . ? C37' C36' H36' 118.0 . . ? C35' C36' H36' 118.0 . . ? C36' C37' C38' 116.5(13) . . ? C36' C37' H37' 121.8 . . ? C38' C37' H37' 121.8 . . ? C39' C38' C37' 119.1(12) . . ? C39' C38' H38' 120.4 . . ? C37' C38' H38' 120.4 . . ? C34' C39' C38' 121.2(12) . . ? C34' C39' H39' 119.4 . . ? C38' C39' H39' 119.4 . . ? C1 N1 C10 121.0(3) . . ? C1 N1 Fe1 116.4(2) . . ? C10 N1 Fe1 122.33(18) . . ? C9 N2 C5 120.0(3) . . ? C9 N2 Fe1 119.1(2) . . ? C5 N2 Fe1 120.4(2) . . ? C2 N3 C22 119.6(3) . . ? C2 N3 Fe1 115.3(2) . . ? C22 N3 Fe1 125.08(18) . . ? Cl3 C1S Cl2 112.6(3) . . ? Cl3 C1S H1S1 109.1 . . ? Cl2 C1S H1S1 109.1 . . ? Cl3 C1S H1S2 109.1 . . ? Cl2 C1S H1S2 109.1 . . ? H1S1 C1S H1S2 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C5 N2 1.6(4) . . . . ? C3 C1 C5 N2 -178.9(3) . . . . ? N1 C1 C5 C6 179.9(3) . . . . ? C3 C1 C5 C6 -0.6(5) . . . . ? N2 C5 C6 C7 -1.4(5) . . . . ? C1 C5 C6 C7 -179.6(3) . . . . ? C5 C6 C7 C8 2.4(5) . . . . ? C6 C7 C8 C9 -0.6(5) . . . . ? C7 C8 C9 N2 -2.4(5) . . . . ? C7 C8 C9 C2 173.0(3) . . . . ? N3 C2 C9 N2 0.3(4) . . . . ? C4 C2 C9 N2 177.4(3) . . . . ? N3 C2 C9 C8 -175.4(3) . . . . ? C4 C2 C9 C8 1.6(5) . . . . ? C15 C10 C11 C12 1.0(5) . . . . ? N1 C10 C11 C12 177.2(3) . . . . ? C15 C10 C11 C16 177.9(3) . . . . ? N1 C10 C11 C16 -5.9(4) . . . . ? C10 C11 C12 C13 0.0(5) . . . . ? C16 C11 C12 C13 -176.9(3) . . . . ? C11 C12 C13 C14 -1.3(5) . . . . ? C12 C13 C14 C15 1.6(6) . . . . ? C11 C10 C15 C14 -0.8(5) . . . . ? N1 C10 C15 C14 -176.8(3) . . . . ? C11 C10 C15 C19 176.4(3) . . . . ? N1 C10 C15 C19 0.4(5) . . . . ? C13 C14 C15 C10 -0.6(5) . . . . ? C13 C14 C15 C19 -177.9(4) . . . . ? C12 C11 C16 C17 84.5(4) . . . . ? C10 C11 C16 C17 -92.3(4) . . . . ? C12 C11 C16 C18 -38.6(4) . . . . ? C10 C11 C16 C18 144.6(3) . . . . ? C10 C15 C19 C21 -117.3(4) . . . . ? C14 C15 C19 C21 59.9(4) . . . . ? C10 C15 C19 C20 118.3(4) . . . . ? C14 C15 C19 C20 -64.6(5) . . . . ? C27 C22 C23 C24 -4.4(4) . . . . ? N3 C22 C23 C24 176.7(3) . . . . ? C27 C22 C23 C28 179.6(3) . . . . ? N3 C22 C23 C28 0.7(4) . . . . ? C22 C23 C24 C25 0.7(5) . . . . ? C28 C23 C24 C25 176.7(3) . . . . ? C23 C24 C25 C26 2.4(5) . . . . ? C24 C25 C26 C27 -1.8(5) . . . . ? C25 C26 C27 C22 -1.7(5) . . . . ? C25 C26 C27 C31 177.7(3) . . . . ? C23 C22 C27 C26 4.9(4) . . . . ? N3 C22 C27 C26 -176.3(3) . . . . ? C23 C22 C27 C31 -174.5(3) . . . . ? N3 C22 C27 C31 4.3(4) . . . . ? C24 C23 C28 C30 -72.4(4) . . . . ? C22 C23 C28 C30 103.5(4) . . . . ? C24 C23 C28 C29 52.2(4) . . . . ? C22 C23 C28 C29 -131.9(3) . . . . ? C26 C27 C31 C33 -70.1(4) . . . . ? C22 C27 C31 C33 109.2(4) . . . . ? C26 C27 C31 C32 54.5(4) . . . . ? C22 C27 C31 C32 -126.2(3) . . . . ? N2 Fe1 S1 C34 -6.0(5) . . . . ? N3 Fe1 S1 C34 68.2(5) . . . . ? N1 Fe1 S1 C34 -80.4(5) . . . . ? Cl1 Fe1 S1 C34 172.9(5) . . . . ? Fe1 S1 C34 C35 81(3) . . . . ? Fe1 S1 C34 C39 -100(3) . . . . ? C39 C34 C35 C36 2(4) . . . . ? S1 C34 C35 C36 -179(2) . . . . ? C34 C35 C36 C37 -1(3) . . . . ? C35 C36 C37 C38 0.0(14) . . . . ? C36 C37 C38 C39 -0.7(12) . . . . ? C37 C38 C39 C34 2(2) . . . . ? C35 C34 C39 C38 -3(4) . . . . ? S1 C34 C39 C38 178.6(19) . . . . ? C39' C34' C35' C36' 0(7) . . . . ? C34' C35' C36' C37' 5(5) . . . . ? C35' C36' C37' C38' -10(3) . . . . ? C36' C37' C38' C39' 10(2) . . . . ? C35' C34' C39' C38' 1(7) . . . . ? C37' C38' C39' C34' -6(4) . . . . ? C3 C1 N1 C10 2.5(5) . . . . ? C5 C1 N1 C10 -178.1(3) . . . . ? C3 C1 N1 Fe1 -171.6(3) . . . . ? C5 C1 N1 Fe1 7.8(3) . . . . ? C15 C10 N1 C1 -82.8(4) . . . . ? C11 C10 N1 C1 101.0(3) . . . . ? C15 C10 N1 Fe1 90.9(3) . . . . ? C11 C10 N1 Fe1 -85.3(3) . . . . ? N2 Fe1 N1 C1 -10.4(2) . . . . ? N3 Fe1 N1 C1 -43.8(3) . . . . ? Cl1 Fe1 N1 C1 -163.7(2) . . . . ? S1 Fe1 N1 C1 80.8(2) . . . . ? N2 Fe1 N1 C10 175.6(2) . . . . ? N3 Fe1 N1 C10 142.2(2) . . . . ? Cl1 Fe1 N1 C10 22.3(2) . . . . ? S1 Fe1 N1 C10 -93.2(2) . . . . ? C8 C9 N2 C5 3.5(4) . . . . ? C2 C9 N2 C5 -172.4(3) . . . . ? C8 C9 N2 Fe1 -168.3(2) . . . . ? C2 C9 N2 Fe1 15.8(3) . . . . ? C6 C5 N2 C9 -1.6(4) . . . . ? C1 C5 N2 C9 176.8(3) . . . . ? C6 C5 N2 Fe1 170.2(2) . . . . ? C1 C5 N2 Fe1 -11.4(3) . . . . ? N3 Fe1 N2 C9 -17.6(2) . . . . ? N1 Fe1 N2 C9 -176.5(2) . . . . ? Cl1 Fe1 N2 C9 -97.6(2) . . . . ? S1 Fe1 N2 C9 80.0(2) . . . . ? N3 Fe1 N2 C5 170.6(2) . . . . ? N1 Fe1 N2 C5 11.7(2) . . . . ? Cl1 Fe1 N2 C5 90.6(3) . . . . ? S1 Fe1 N2 C5 -91.8(2) . . . . ? C9 C2 N3 C22 168.6(3) . . . . ? C4 C2 N3 C22 -8.3(4) . . . . ? C9 C2 N3 Fe1 -14.7(3) . . . . ? C4 C2 N3 Fe1 168.4(2) . . . . ? C23 C22 N3 C2 -99.8(3) . . . . ? C27 C22 N3 C2 81.4(4) . . . . ? C23 C22 N3 Fe1 83.9(3) . . . . ? C27 C22 N3 Fe1 -95.0(3) . . . . ? N2 Fe1 N3 C2 17.3(2) . . . . ? N1 Fe1 N3 C2 50.7(3) . . . . ? Cl1 Fe1 N3 C2 170.5(2) . . . . ? S1 Fe1 N3 C2 -75.5(2) . . . . ? N2 Fe1 N3 C22 -166.2(2) . . . . ? N1 Fe1 N3 C22 -132.8(2) . . . . ? Cl1 Fe1 N3 C22 -13.0(2) . . . . ? S1 Fe1 N3 C22 101.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.502 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.052