# 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_14ch2cl2100ka _database_code_depnum_ccdc_archive 'CCDC 921061' #TrackingRef '17077_web_deposit_cif_file_0_OlivierRoubeau_1358848554.Cpd1-14ch2cl2100ka.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H36 Fe N14 O4 S2, 2(C H2 Cl2)' _chemical_formula_sum 'C54 H40 Cl4 Fe N14 O4 S2' _chemical_formula_weight 1210.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0020 0.0020 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' H H 0.0000 0.0000 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' N N -0.0031 0.0040 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' O O -0.0041 0.0074 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' S S 0.1206 0.1480 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Cl Cl 0.1408 0.1896 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Fe Fe 0.2064 0.9930 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1377(7) _cell_length_b 10.8050(7) _cell_length_c 13.0202(9) _cell_angle_alpha 83.376(2) _cell_angle_beta 78.242(2) _cell_angle_gamma 70.723(2) _cell_volume 1316.21(15) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8267 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 33.59 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details 'SADABS Bruker AXS Madison WI US' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18860 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0747 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 33.60 _reflns_number_total 7887 _reflns_number_gt 6891 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.68a' _computing_data_reduction 'Bruker SAINT v7.68a' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogens were refined anisotropically. Hydrogens were placed geometrically on their carrier atom and refined with a riding model. ; _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^)+(0.1169P)^2^+0.2551P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7887 _refine_ls_number_parameters 358 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1837 _refine_ls_wR_factor_gt 0.1770 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.5000 0.5000 0.5000 0.01045(11) Uani 1 2 d S . . S1 S 0.39345(5) 0.18948(5) 0.32941(4) 0.02078(13) Uani 1 1 d . . . O1 O 0.20502(15) 0.89147(14) 0.90879(13) 0.0217(3) Uani 1 1 d . . . O2 O 0.63594(14) 0.60106(14) 0.93778(11) 0.0182(3) Uani 1 1 d . . . N1 N 0.46335(16) 0.37446(15) 0.42319(12) 0.0146(3) Uani 1 1 d . . . N2 N 0.29519(15) 0.55398(14) 0.56506(12) 0.0127(3) Uani 1 1 d . . . N3 N 0.53052(16) 0.36460(15) 0.61669(12) 0.0129(3) Uani 1 1 d . . . N4 N 0.36034(15) 0.51705(14) 0.73148(12) 0.0127(3) Uani 1 1 d . . . N5 N 0.28167(16) 0.71352(16) 0.81493(13) 0.0165(3) Uani 1 1 d . . . N6 N 0.49951(16) 0.54962(15) 0.83797(12) 0.0142(3) Uani 1 1 d . . . N7 N 0.42133(17) 0.74397(16) 0.93184(13) 0.0170(3) Uani 1 1 d . . . C1 C 0.43294(19) 0.29741(18) 0.38590(14) 0.0149(3) Uani 1 1 d . . . C3 C 0.19337(19) 0.58529(18) 0.50498(15) 0.0168(3) Uani 1 1 d . . . H3A H 0.2219 0.5762 0.4313 0.020 Uiso 1 1 calc R . . C4 C 0.0502(2) 0.6298(2) 0.54549(16) 0.0192(4) Uani 1 1 d . . . H4A H -0.0180 0.6528 0.5004 0.023 Uiso 1 1 calc R . . C5 C 0.0075(2) 0.6403(2) 0.65333(16) 0.0212(4) Uani 1 1 d . . . H5A H -0.0904 0.6718 0.6832 0.025 Uiso 1 1 calc R . . C6 C 0.10976(19) 0.6041(2) 0.71660(15) 0.0186(3) Uani 1 1 d . . . H6A H 0.0834 0.6084 0.7907 0.022 Uiso 1 1 calc R . . C7 C 0.25200(18) 0.56142(17) 0.66954(13) 0.0130(3) Uani 1 1 d . . . C8 C 0.62109(19) 0.24135(18) 0.60016(15) 0.0164(3) Uani 1 1 d . . . H8A H 0.6672 0.2197 0.5304 0.020 Uiso 1 1 calc R . . C9 C 0.6493(2) 0.14618(18) 0.67978(16) 0.0185(3) Uani 1 1 d . . . H9A H 0.7148 0.0615 0.6651 0.022 Uiso 1 1 calc R . . C10 C 0.5803(2) 0.17590(19) 0.78190(15) 0.0186(3) Uani 1 1 d . . . H10A H 0.6001 0.1130 0.8387 0.022 Uiso 1 1 calc R . . C11 C 0.4822(2) 0.29924(18) 0.79902(14) 0.0166(3) Uani 1 1 d . . . H11A H 0.4300 0.3213 0.8674 0.020 Uiso 1 1 calc R . . C12 C 0.46176(18) 0.38974(17) 0.71476(14) 0.0133(3) Uani 1 1 d . . . C13 C 0.38007(18) 0.59722(17) 0.79776(13) 0.0135(3) Uani 1 1 d . . . C14 C 0.30829(19) 0.77881(18) 0.88499(15) 0.0169(3) Uani 1 1 d . . . C15 C 0.51484(19) 0.63036(18) 0.89911(14) 0.0148(3) Uani 1 1 d . . . C16 C 0.2200(2) 0.97066(18) 0.98093(15) 0.0174(3) Uani 1 1 d . . . C17 C 0.1255(2) 0.98783(19) 1.07463(16) 0.0201(4) Uani 1 1 d . . . H17A H 0.0596 0.9401 1.0920 0.024 Uiso 1 1 calc R . . C18 C 0.1280(2) 1.0762(2) 1.14336(16) 0.0211(4) Uani 1 1 d . . . H18A H 0.0620 1.0911 1.2075 0.025 Uiso 1 1 calc R . . C19 C 0.2280(2) 1.14289(18) 1.11769(15) 0.0177(3) Uani 1 1 d . . . H19A H 0.2305 1.2029 1.1646 0.021 Uiso 1 1 calc R . . C20 C 0.3236(2) 1.12170(19) 1.02396(16) 0.0188(3) Uani 1 1 d . . . H20A H 0.3928 1.1659 1.0077 0.023 Uiso 1 1 calc R . . C21 C 0.3194(2) 1.03655(19) 0.95361(16) 0.0192(3) Uani 1 1 d . . . H21A H 0.3830 1.0238 0.8883 0.023 Uiso 1 1 calc R . . C22 C 0.75707(19) 0.49790(18) 0.90410(15) 0.0176(3) Uani 1 1 d . . . C23 C 0.7984(2) 0.4514(2) 0.80370(19) 0.0294(5) Uani 1 1 d . . . H23A H 0.7405 0.4869 0.7517 0.035 Uiso 1 1 calc R . . C24 C 0.9265(2) 0.3517(3) 0.7811(2) 0.0342(5) Uani 1 1 d . . . H24A H 0.9553 0.3172 0.7133 0.041 Uiso 1 1 calc R . . C25 C 1.0129(2) 0.3019(2) 0.8556(2) 0.0335(5) Uani 1 1 d . . . H25A H 1.1004 0.2338 0.8389 0.040 Uiso 1 1 calc R . . C26 C 0.9716(3) 0.3512(3) 0.9534(2) 0.0419(7) Uani 1 1 d . . . H26A H 1.0307 0.3172 1.0048 0.050 Uiso 1 1 calc R . . C27 C 0.8435(2) 0.4510(3) 0.97799(18) 0.0305(5) Uani 1 1 d . . . H27A H 0.8160 0.4864 1.0454 0.037 Uiso 1 1 calc R . . Cl2 Cl 0.72225(8) 0.82199(9) 0.36494(6) 0.0495(2) Uani 1 1 d . . . Cl1 Cl 0.88365(7) 0.97555(8) 0.42099(7) 0.0487(2) Uani 1 1 d . . . C28 C 0.7146(3) 0.9704(3) 0.4122(2) 0.0408(6) Uani 1 1 d . . . H28A H 0.6537 0.9821 0.4825 0.049 Uiso 1 1 calc R . . H28B H 0.6704 1.0441 0.3647 0.049 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 0.01104(18) 0.00995(18) 0.01058(18) -0.00191(12) -0.00292(12) -0.00252(12) S1 0.0225(2) 0.0189(2) 0.0255(3) -0.00629(18) -0.00841(18) -0.00846(18) O1 0.0143(6) 0.0198(7) 0.0313(8) -0.0141(6) -0.0089(5) 0.0015(5) O2 0.0167(6) 0.0212(7) 0.0178(6) -0.0069(5) -0.0046(5) -0.0047(5) N1 0.0149(6) 0.0150(7) 0.0142(7) -0.0020(5) -0.0029(5) -0.0043(5) N2 0.0119(6) 0.0134(6) 0.0134(7) -0.0030(5) -0.0038(5) -0.0030(5) N3 0.0135(6) 0.0125(6) 0.0134(6) -0.0018(5) -0.0036(5) -0.0040(5) N4 0.0125(6) 0.0116(6) 0.0136(6) -0.0031(5) -0.0035(5) -0.0015(5) N5 0.0135(7) 0.0163(7) 0.0198(7) -0.0059(6) -0.0046(5) -0.0024(5) N6 0.0145(7) 0.0147(7) 0.0138(7) -0.0021(5) -0.0038(5) -0.0037(5) N7 0.0149(7) 0.0167(7) 0.0199(7) -0.0071(6) -0.0042(5) -0.0028(6) C1 0.0145(7) 0.0147(7) 0.0149(8) -0.0004(6) -0.0047(6) -0.0028(6) C3 0.0160(8) 0.0184(8) 0.0161(8) -0.0019(6) -0.0058(6) -0.0036(6) C4 0.0145(8) 0.0220(9) 0.0215(9) -0.0047(7) -0.0066(6) -0.0032(7) C5 0.0141(8) 0.0265(10) 0.0218(9) -0.0070(7) -0.0036(6) -0.0025(7) C6 0.0133(8) 0.0244(9) 0.0172(8) -0.0059(7) -0.0014(6) -0.0038(7) C7 0.0131(7) 0.0129(7) 0.0133(7) -0.0022(6) -0.0027(5) -0.0035(6) C8 0.0170(8) 0.0130(8) 0.0175(8) -0.0026(6) -0.0032(6) -0.0019(6) C9 0.0199(8) 0.0104(7) 0.0226(9) -0.0015(6) -0.0044(7) -0.0005(6) C10 0.0197(8) 0.0155(8) 0.0186(8) 0.0024(6) -0.0037(6) -0.0037(7) C11 0.0187(8) 0.0161(8) 0.0148(8) 0.0001(6) -0.0040(6) -0.0050(6) C12 0.0127(7) 0.0122(7) 0.0153(8) -0.0026(6) -0.0038(6) -0.0031(6) C13 0.0142(7) 0.0148(8) 0.0120(7) -0.0021(6) -0.0025(5) -0.0047(6) C14 0.0138(8) 0.0166(8) 0.0208(8) -0.0067(6) -0.0042(6) -0.0027(6) C15 0.0134(7) 0.0152(8) 0.0156(8) -0.0017(6) -0.0045(6) -0.0027(6) C16 0.0160(8) 0.0150(8) 0.0218(9) -0.0072(6) -0.0070(6) -0.0013(6) C17 0.0156(8) 0.0192(9) 0.0254(9) -0.0041(7) -0.0043(7) -0.0040(7) C18 0.0175(8) 0.0210(9) 0.0215(9) -0.0048(7) -0.0033(7) -0.0008(7) C19 0.0200(8) 0.0139(8) 0.0195(8) -0.0032(6) -0.0091(6) -0.0014(6) C20 0.0198(8) 0.0154(8) 0.0226(9) -0.0018(7) -0.0072(7) -0.0052(7) C21 0.0173(8) 0.0189(8) 0.0209(9) -0.0040(7) -0.0043(6) -0.0036(7) C22 0.0133(8) 0.0167(8) 0.0216(9) -0.0012(6) -0.0033(6) -0.0029(6) C23 0.0191(9) 0.0364(12) 0.0298(11) -0.0155(9) -0.0087(8) 0.0022(8) C24 0.0206(10) 0.0367(13) 0.0409(13) -0.0182(10) -0.0021(9) 0.0002(9) C25 0.0205(10) 0.0269(11) 0.0423(14) 0.0051(10) -0.0011(9) 0.0019(8) C26 0.0232(11) 0.0550(17) 0.0282(12) 0.0140(11) -0.0065(9) 0.0093(11) C27 0.0204(9) 0.0440(14) 0.0189(9) 0.0031(9) -0.0060(7) 0.0010(9) Cl2 0.0405(4) 0.0688(5) 0.0464(4) -0.0240(4) 0.0012(3) -0.0253(4) Cl1 0.0326(3) 0.0496(4) 0.0672(5) -0.0084(4) -0.0097(3) -0.0152(3) C28 0.0263(11) 0.0470(16) 0.0451(15) -0.0129(12) -0.0094(10) -0.0011(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N1 1.9431(16) . ? Fe1 N1 1.9431(16) 2_666 ? Fe1 N3 1.9810(15) . ? Fe1 N3 1.9810(15) 2_666 ? Fe1 N2 1.9916(15) . ? Fe1 N2 1.9916(15) 2_666 ? S1 C1 1.6393(19) . ? O1 C14 1.337(2) . ? O1 C16 1.403(2) . ? O2 C15 1.349(2) . ? O2 C22 1.390(2) . ? N1 C1 1.161(2) . ? N2 C7 1.345(2) . ? N2 C3 1.352(2) . ? N3 C12 1.335(2) . ? N3 C8 1.357(2) . ? N4 C13 1.376(2) . ? N4 C7 1.418(2) . ? N4 C12 1.429(2) . ? N5 C13 1.331(2) . ? N5 C14 1.333(2) . ? N6 C15 1.311(2) . ? N6 C13 1.338(2) . ? N7 C14 1.332(2) . ? N7 C15 1.332(2) . ? C3 C4 1.379(3) . ? C3 H3A 0.9500 . ? C4 C5 1.389(3) . ? C4 H4A 0.9500 . ? C5 C6 1.383(3) . ? C5 H5A 0.9500 . ? C6 C7 1.391(2) . ? C6 H6A 0.9500 . ? C8 C9 1.376(3) . ? C8 H8A 0.9500 . ? C9 C10 1.390(3) . ? C9 H9A 0.9500 . ? C10 C11 1.385(3) . ? C10 H10A 0.9500 . ? C11 C12 1.383(2) . ? C11 H11A 0.9500 . ? C16 C17 1.378(3) . ? C16 C21 1.384(3) . ? C17 C18 1.392(3) . ? C17 H17A 0.9500 . ? C18 C19 1.395(3) . ? C18 H18A 0.9500 . ? C19 C20 1.385(3) . ? C19 H19A 0.9500 . ? C20 C21 1.387(3) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C27 1.374(3) . ? C22 C23 1.388(3) . ? C23 C24 1.388(3) . ? C23 H23A 0.9500 . ? C24 C25 1.382(4) . ? C24 H24A 0.9500 . ? C25 C26 1.369(4) . ? C25 H25A 0.9500 . ? C26 C27 1.391(3) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? Cl2 C28 1.756(3) . ? Cl1 C28 1.760(3) . ? C28 H28A 0.9900 . ? C28 H28B 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 N1 Fe1 N1 179.999(1) . 2_666 ? N1 Fe1 N3 87.86(6) . . ? N1 Fe1 N3 92.14(6) 2_666 . ? N1 Fe1 N3 92.14(6) . 2_666 ? N1 Fe1 N3 87.86(6) 2_666 2_666 ? N3 Fe1 N3 179.999(1) . 2_666 ? N1 Fe1 N2 87.77(6) . . ? N1 Fe1 N2 92.23(6) 2_666 . ? N3 Fe1 N2 86.75(6) . . ? N3 Fe1 N2 93.25(6) 2_666 . ? N1 Fe1 N2 92.23(6) . 2_666 ? N1 Fe1 N2 87.77(6) 2_666 2_666 ? N3 Fe1 N2 93.25(6) . 2_666 ? N3 Fe1 N2 86.75(6) 2_666 2_666 ? N2 Fe1 N2 180.0 . 2_666 ? C14 O1 C16 119.05(14) . . ? C15 O2 C22 123.21(15) . . ? C1 N1 Fe1 173.52(16) . . ? C7 N2 C3 117.22(15) . . ? C7 N2 Fe1 121.95(11) . . ? C3 N2 Fe1 120.83(12) . . ? C12 N3 C8 116.95(15) . . ? C12 N3 Fe1 121.66(12) . . ? C8 N3 Fe1 121.38(12) . . ? C13 N4 C7 122.28(14) . . ? C13 N4 C12 119.15(14) . . ? C7 N4 C12 118.16(14) . . ? C13 N5 C14 112.47(15) . . ? C15 N6 C13 113.41(15) . . ? C14 N7 C15 111.72(16) . . ? N1 C1 S1 178.02(18) . . ? N2 C3 C4 123.15(17) . . ? N2 C3 H3A 118.4 . . ? C4 C3 H3A 118.4 . . ? C3 C4 C5 118.82(17) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? C6 C5 C4 118.95(17) . . ? C6 C5 H5A 120.5 . . ? C4 C5 H5A 120.5 . . ? C5 C6 C7 118.69(17) . . ? C5 C6 H6A 120.7 . . ? C7 C6 H6A 120.7 . . ? N2 C7 C6 123.08(16) . . ? N2 C7 N4 116.17(15) . . ? C6 C7 N4 120.68(16) . . ? N3 C8 C9 123.07(17) . . ? N3 C8 H8A 118.5 . . ? C9 C8 H8A 118.5 . . ? C8 C9 C10 118.97(17) . . ? C8 C9 H9A 120.5 . . ? C10 C9 H9A 120.5 . . ? C11 C10 C9 118.49(17) . . ? C11 C10 H10A 120.8 . . ? C9 C10 H10A 120.8 . . ? C12 C11 C10 118.77(17) . . ? C12 C11 H11A 120.6 . . ? C10 C11 H11A 120.6 . . ? N3 C12 C11 123.62(16) . . ? N3 C12 N4 117.15(15) . . ? C11 C12 N4 119.22(16) . . ? N5 C13 N6 126.32(16) . . ? N5 C13 N4 118.05(15) . . ? N6 C13 N4 115.63(15) . . ? N7 C14 N5 127.88(17) . . ? N7 C14 O1 119.02(16) . . ? N5 C14 O1 113.10(16) . . ? N6 C15 N7 127.70(16) . . ? N6 C15 O2 120.19(16) . . ? N7 C15 O2 112.11(16) . . ? C17 C16 C21 122.26(18) . . ? C17 C16 O1 117.49(17) . . ? C21 C16 O1 120.05(18) . . ? C16 C17 C18 118.95(18) . . ? C16 C17 H17A 120.5 . . ? C18 C17 H17A 120.5 . . ? C17 C18 C19 119.69(18) . . ? C17 C18 H18A 120.2 . . ? C19 C18 H18A 120.2 . . ? C20 C19 C18 120.10(17) . . ? C20 C19 H19A 120.0 . . ? C18 C19 H19A 120.0 . . ? C19 C20 C21 120.65(18) . . ? C19 C20 H20A 119.7 . . ? C21 C20 H20A 119.7 . . ? C16 C21 C20 118.32(18) . . ? C16 C21 H21A 120.8 . . ? C20 C21 H21A 120.8 . . ? C27 C22 C23 120.98(19) . . ? C27 C22 O2 113.31(18) . . ? C23 C22 O2 125.45(18) . . ? C22 C23 C24 118.3(2) . . ? C22 C23 H23A 120.8 . . ? C24 C23 H23A 120.8 . . ? C25 C24 C23 121.2(2) . . ? C25 C24 H24A 119.4 . . ? C23 C24 H24A 119.4 . . ? C26 C25 C24 119.6(2) . . ? C26 C25 H25A 120.2 . . ? C24 C25 H25A 120.2 . . ? C25 C26 C27 120.4(2) . . ? C25 C26 H26A 119.8 . . ? C27 C26 H26A 119.8 . . ? C22 C27 C26 119.6(2) . . ? C22 C27 H27A 120.2 . . ? C26 C27 H27A 120.2 . . ? Cl2 C28 Cl1 112.25(15) . . ? Cl2 C28 H28A 109.2 . . ? Cl1 C28 H28A 109.2 . . ? Cl2 C28 H28B 109.2 . . ? Cl1 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.191 _refine_diff_density_min -0.831 _refine_diff_density_rms 0.126 data_14ch2cl2240ka _database_code_depnum_ccdc_archive 'CCDC 921062' #TrackingRef '17078_web_deposit_cif_file_1_OlivierRoubeau_1358848554.Cpd1-14ch2cl2240ka.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H36 Fe N14 O4 S2, 2(C H2 Cl2)' _chemical_formula_sum 'C54 H40 Cl4 Fe N14 O4 S2' _chemical_formula_weight 1210.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0020 0.0020 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' H H 0.0000 0.0000 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' N N -0.0031 0.0040 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' O O -0.0041 0.0074 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' S S 0.1206 0.1480 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Cl Cl 0.1408 0.1896 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Fe Fe 0.2064 0.9930 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2386(8) _cell_length_b 10.9671(8) _cell_length_c 13.2109(10) _cell_angle_alpha 85.375(2) _cell_angle_beta 79.889(2) _cell_angle_gamma 69.869(2) _cell_volume 1370.84(18) _cell_formula_units_Z 1 _cell_measurement_temperature 240(2) _cell_measurement_reflns_used 9918 _cell_measurement_theta_min 3.33 _cell_measurement_theta_max 33.60 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 0.763 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details 'SADABS Bruker AXS Madison WI US' _exptl_special_details ; ? ; _diffrn_ambient_temperature 240(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 39494 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 33.62 _reflns_number_total 8326 _reflns_number_gt 6844 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.68a' _computing_data_reduction 'Bruker SAINT v7.68a' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogens were refined anisotropically. One of the phenyl ring carbons were refined with displacement parametrs restraints (C23>C27). Hydrogens were placed geometrically on their carrier atom and refined with a riding model. ; _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^)+(0.1208P)^2^+0.5153P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8326 _refine_ls_number_parameters 358 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.2088 _refine_ls_wR_factor_gt 0.1984 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.5000 0.5000 0.5000 0.02951(13) Uani 1 2 d S . . S1 S 0.39797(8) 0.18497(8) 0.32156(6) 0.0568(2) Uani 1 1 d . . . O1 O 0.20703(17) 0.88949(18) 0.90761(16) 0.0487(5) Uani 1 1 d . . . O2 O 0.63522(17) 0.59789(17) 0.93768(13) 0.0413(4) Uani 1 1 d . . . N1 N 0.4605(2) 0.3693(2) 0.41767(15) 0.0426(4) Uani 1 1 d . . . N2 N 0.2823(2) 0.5580(2) 0.57335(15) 0.0389(4) Uani 1 1 d . . . N3 N 0.5312(2) 0.35853(18) 0.62381(15) 0.0364(4) Uani 1 1 d . . . N4 N 0.35865(18) 0.51348(16) 0.73368(13) 0.0308(3) Uani 1 1 d . . . N5 N 0.28094(18) 0.70989(18) 0.81661(15) 0.0351(4) Uani 1 1 d . . . N6 N 0.49918(18) 0.54740(17) 0.83784(13) 0.0323(3) Uani 1 1 d . . . N7 N 0.42187(19) 0.74199(19) 0.93072(15) 0.0366(4) Uani 1 1 d . . . C1 C 0.4332(2) 0.2925(2) 0.37934(17) 0.0377(4) Uani 1 1 d . . . C3 C 0.1778(3) 0.5929(3) 0.5160(2) 0.0528(6) Uani 1 1 d . . . H3A H 0.2020 0.5906 0.4440 0.063 Uiso 1 1 calc R . . C4 C 0.0381(3) 0.6314(3) 0.5579(3) 0.0569(7) Uani 1 1 d . . . H4A H -0.0319 0.6564 0.5155 0.068 Uiso 1 1 calc R . . C5 C 0.0025(3) 0.6325(4) 0.6628(3) 0.0622(8) Uani 1 1 d . . . H5A H -0.0928 0.6599 0.6933 0.075 Uiso 1 1 calc R . . C6 C 0.1075(3) 0.5932(3) 0.7238(2) 0.0515(6) Uani 1 1 d . . . H6A H 0.0855 0.5907 0.7959 0.062 Uiso 1 1 calc R . . C7 C 0.2455(2) 0.5579(2) 0.67522(17) 0.0346(4) Uani 1 1 d . . . C8 C 0.6220(3) 0.2371(2) 0.6083(2) 0.0459(5) Uani 1 1 d . . . H8A H 0.6708 0.2147 0.5416 0.055 Uiso 1 1 calc R . . C9 C 0.6468(3) 0.1444(2) 0.6854(2) 0.0511(6) Uani 1 1 d . . . H9A H 0.7126 0.0609 0.6718 0.061 Uiso 1 1 calc R . . C10 C 0.5742(3) 0.1754(2) 0.7827(2) 0.0495(6) Uani 1 1 d . . . H10A H 0.5906 0.1140 0.8371 0.059 Uiso 1 1 calc R . . C11 C 0.4767(3) 0.2980(2) 0.79938(19) 0.0416(5) Uani 1 1 d . . . H11A H 0.4235 0.3211 0.8648 0.050 Uiso 1 1 calc R . . C12 C 0.4590(2) 0.38605(19) 0.71783(16) 0.0327(4) Uani 1 1 d . . . C13 C 0.3791(2) 0.59424(19) 0.79867(14) 0.0295(3) Uani 1 1 d . . . C14 C 0.3091(2) 0.7759(2) 0.88514(17) 0.0356(4) Uani 1 1 d . . . C15 C 0.5143(2) 0.6279(2) 0.89880(15) 0.0317(4) Uani 1 1 d . . . C16 C 0.2228(2) 0.9699(2) 0.97847(19) 0.0388(5) Uani 1 1 d . . . C17 C 0.1314(2) 0.9912(2) 1.0693(2) 0.0440(5) Uani 1 1 d . . . H17A H 0.0673 0.9457 1.0860 0.053 Uiso 1 1 calc R . . C18 C 0.1344(3) 1.0807(3) 1.1365(2) 0.0485(6) Uani 1 1 d . . . H18A H 0.0715 1.0974 1.1988 0.058 Uiso 1 1 calc R . . C19 C 0.2309(3) 1.1452(2) 1.1108(2) 0.0471(6) Uani 1 1 d . . . H19A H 0.2332 1.2063 1.1559 0.056 Uiso 1 1 calc R . . C20 C 0.3233(3) 1.1207(2) 1.0200(2) 0.0468(5) Uani 1 1 d . . . H20A H 0.3900 1.1635 1.0042 0.056 Uiso 1 1 calc R . . C21 C 0.3189(3) 1.0336(3) 0.9518(2) 0.0447(5) Uani 1 1 d . . . H21A H 0.3802 1.0182 0.8887 0.054 Uiso 1 1 calc R . . C22 C 0.7554(2) 0.4943(2) 0.9039(2) 0.0399(5) Uani 1 1 d . . . C23 C 0.7952(3) 0.4483(4) 0.8052(3) 0.0780(12) Uani 1 1 d U . . H23A H 0.7371 0.4836 0.7549 0.094 Uiso 1 1 calc R . . C24 C 0.9225(4) 0.3491(5) 0.7817(4) 0.0897(13) Uani 1 1 d U . . H24A H 0.9509 0.3163 0.7148 0.108 Uiso 1 1 calc R . . C25 C 1.0081(4) 0.2980(4) 0.8553(4) 0.0822(10) Uani 1 1 d U . . H25A H 1.0937 0.2297 0.8392 0.099 Uiso 1 1 calc R . . C26 C 0.9678(4) 0.3467(5) 0.9499(3) 0.0952(14) Uani 1 1 d U . . H26A H 1.0265 0.3126 1.0000 0.114 Uiso 1 1 calc R . . C27 C 0.8411(3) 0.4466(4) 0.9754(3) 0.0738(11) Uani 1 1 d U . . H27A H 0.8150 0.4808 1.0418 0.089 Uiso 1 1 calc R . . Cl2 Cl 0.72938(18) 0.8095(2) 0.37174(14) 0.1337(6) Uani 1 1 d . . . Cl1 Cl 0.8795(2) 0.9766(2) 0.4159(2) 0.1590(8) Uani 1 1 d . . . C28 C 0.7171(6) 0.9489(8) 0.4148(6) 0.134(3) Uani 1 1 d . . . H28A H 0.6656 0.9572 0.4853 0.161 Uiso 1 1 calc R . . H28B H 0.6603 1.0180 0.3730 0.161 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 0.0345(2) 0.0290(2) 0.0260(2) -0.00401(14) -0.00729(14) -0.00989(15) S1 0.0621(4) 0.0548(4) 0.0656(4) -0.0150(3) -0.0203(3) -0.0269(3) O1 0.0328(7) 0.0439(9) 0.0675(12) -0.0294(8) -0.0174(7) 0.0004(7) O2 0.0378(8) 0.0420(8) 0.0449(9) -0.0137(7) -0.0164(6) -0.0067(6) N1 0.0526(11) 0.0456(10) 0.0338(9) -0.0051(8) -0.0066(8) -0.0210(9) N2 0.0414(9) 0.0423(10) 0.0365(9) -0.0025(7) -0.0166(7) -0.0130(8) N3 0.0395(9) 0.0291(8) 0.0378(9) -0.0074(7) -0.0072(7) -0.0059(7) N4 0.0327(8) 0.0288(8) 0.0311(8) -0.0063(6) -0.0102(6) -0.0067(6) N5 0.0306(8) 0.0340(8) 0.0402(9) -0.0126(7) -0.0096(7) -0.0055(6) N6 0.0329(8) 0.0307(8) 0.0329(8) -0.0061(6) -0.0097(6) -0.0069(6) N7 0.0330(8) 0.0380(9) 0.0385(9) -0.0133(7) -0.0090(7) -0.0074(7) C1 0.0391(10) 0.0383(10) 0.0361(10) -0.0025(8) -0.0097(8) -0.0114(8) C3 0.0540(14) 0.0618(16) 0.0479(14) -0.0001(12) -0.0272(11) -0.0171(12) C4 0.0462(13) 0.0619(16) 0.0655(17) -0.0076(13) -0.0307(12) -0.0097(12) C5 0.0353(12) 0.076(2) 0.0728(19) -0.0266(16) -0.0175(12) -0.0054(12) C6 0.0349(11) 0.0675(17) 0.0506(14) -0.0206(12) -0.0087(10) -0.0104(11) C7 0.0350(9) 0.0314(9) 0.0384(10) -0.0086(7) -0.0129(8) -0.0070(7) C8 0.0504(13) 0.0317(10) 0.0472(12) -0.0093(9) -0.0039(10) -0.0032(9) C9 0.0525(14) 0.0293(10) 0.0638(16) -0.0050(10) -0.0115(12) -0.0020(9) C10 0.0558(14) 0.0345(11) 0.0562(15) 0.0061(10) -0.0187(11) -0.0093(10) C11 0.0493(12) 0.0357(10) 0.0383(11) -0.0010(8) -0.0103(9) -0.0106(9) C12 0.0372(9) 0.0280(9) 0.0338(9) -0.0059(7) -0.0116(7) -0.0080(7) C13 0.0328(8) 0.0294(8) 0.0270(8) -0.0053(6) -0.0059(6) -0.0099(7) C14 0.0309(9) 0.0333(9) 0.0416(10) -0.0123(8) -0.0078(7) -0.0060(7) C15 0.0311(8) 0.0331(9) 0.0316(9) -0.0046(7) -0.0088(7) -0.0089(7) C16 0.0313(9) 0.0323(9) 0.0510(12) -0.0147(9) -0.0133(8) -0.0023(7) C17 0.0333(10) 0.0427(12) 0.0548(14) -0.0091(10) -0.0096(9) -0.0082(8) C18 0.0457(12) 0.0509(14) 0.0430(12) -0.0126(10) -0.0082(10) -0.0057(10) C19 0.0518(13) 0.0359(11) 0.0531(14) -0.0128(10) -0.0244(11) -0.0036(9) C20 0.0491(13) 0.0375(11) 0.0592(15) -0.0057(10) -0.0193(11) -0.0154(10) C21 0.0394(11) 0.0453(12) 0.0498(13) -0.0128(10) -0.0080(9) -0.0117(9) C22 0.0323(9) 0.0364(10) 0.0506(12) -0.0009(9) -0.0124(8) -0.0081(8) C23 0.0422(14) 0.099(3) 0.078(2) -0.041(2) -0.0216(14) 0.0093(15) C24 0.0476(16) 0.099(3) 0.106(3) -0.053(2) -0.0145(17) 0.0083(16) C25 0.0466(15) 0.0600(19) 0.114(2) 0.0072(18) -0.0034(16) 0.0086(13) C26 0.0564(18) 0.112(3) 0.0765(19) 0.0365(18) -0.0157(16) 0.0167(18) C27 0.0467(14) 0.104(3) 0.0476(15) 0.0180(15) -0.0138(11) 0.0032(15) Cl2 0.1042(10) 0.1949(19) 0.1197(12) -0.0464(12) -0.0058(9) -0.0689(12) Cl1 0.1164(13) 0.1502(17) 0.211(2) -0.0400(16) -0.0193(14) -0.0409(12) C28 0.081(3) 0.175(7) 0.128(5) -0.042(5) -0.036(3) -0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N1 2.051(2) 2_666 ? Fe1 N1 2.051(2) . ? Fe1 N3 2.1489(19) 2_666 ? Fe1 N3 2.1489(19) . ? Fe1 N2 2.162(2) . ? Fe1 N2 2.162(2) 2_666 ? S1 C1 1.624(2) . ? O1 C14 1.337(3) . ? O1 C16 1.402(3) . ? O2 C15 1.349(2) . ? O2 C22 1.389(3) . ? N1 C1 1.151(3) . ? N2 C7 1.332(3) . ? N2 C3 1.350(3) . ? N3 C12 1.328(3) . ? N3 C8 1.343(3) . ? N4 C13 1.371(2) . ? N4 C12 1.427(3) . ? N4 C7 1.429(2) . ? N5 C13 1.328(3) . ? N5 C14 1.329(3) . ? N6 C15 1.306(3) . ? N6 C13 1.337(2) . ? N7 C14 1.322(3) . ? N7 C15 1.330(3) . ? C3 C4 1.369(4) . ? C3 H3A 0.9400 . ? C4 C5 1.371(5) . ? C4 H4A 0.9400 . ? C5 C6 1.386(4) . ? C5 H5A 0.9400 . ? C6 C7 1.379(3) . ? C6 H6A 0.9400 . ? C8 C9 1.372(4) . ? C8 H8A 0.9400 . ? C9 C10 1.372(4) . ? C9 H9A 0.9400 . ? C10 C11 1.378(3) . ? C10 H10A 0.9400 . ? C11 C12 1.381(3) . ? C11 H11A 0.9400 . ? C16 C17 1.368(4) . ? C16 C21 1.375(4) . ? C17 C18 1.386(4) . ? C17 H17A 0.9400 . ? C18 C19 1.385(4) . ? C18 H18A 0.9400 . ? C19 C20 1.372(4) . ? C19 H19A 0.9400 . ? C20 C21 1.382(3) . ? C20 H20A 0.9400 . ? C21 H21A 0.9400 . ? C22 C27 1.354(4) . ? C22 C23 1.378(4) . ? C23 C24 1.384(4) . ? C23 H23A 0.9400 . ? C24 C25 1.379(6) . ? C24 H24A 0.9400 . ? C25 C26 1.339(7) . ? C25 H25A 0.9400 . ? C26 C27 1.387(5) . ? C26 H26A 0.9400 . ? C27 H27A 0.9400 . ? Cl2 C28 1.631(8) . ? Cl1 C28 1.792(7) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 179.999(1) 2_666 . ? N1 Fe1 N3 88.12(8) 2_666 2_666 ? N1 Fe1 N3 91.88(8) . 2_666 ? N1 Fe1 N3 91.88(8) 2_666 . ? N1 Fe1 N3 88.12(8) . . ? N3 Fe1 N3 180.00(11) 2_666 . ? N1 Fe1 N2 91.74(8) 2_666 . ? N1 Fe1 N2 88.26(8) . . ? N3 Fe1 N2 96.47(7) 2_666 . ? N3 Fe1 N2 83.53(7) . . ? N1 Fe1 N2 88.26(8) 2_666 2_666 ? N1 Fe1 N2 91.74(8) . 2_666 ? N3 Fe1 N2 83.54(7) 2_666 2_666 ? N3 Fe1 N2 96.46(7) . 2_666 ? N2 Fe1 N2 179.999(1) . 2_666 ? C14 O1 C16 119.14(17) . . ? C15 O2 C22 123.07(17) . . ? C1 N1 Fe1 174.1(2) . . ? C7 N2 C3 117.3(2) . . ? C7 N2 Fe1 122.32(14) . . ? C3 N2 Fe1 120.31(18) . . ? C12 N3 C8 117.2(2) . . ? C12 N3 Fe1 121.62(14) . . ? C8 N3 Fe1 121.10(16) . . ? C13 N4 C12 119.22(16) . . ? C13 N4 C7 121.28(16) . . ? C12 N4 C7 119.29(16) . . ? C13 N5 C14 112.55(17) . . ? C15 N6 C13 113.32(17) . . ? C14 N7 C15 111.77(17) . . ? N1 C1 S1 178.0(2) . . ? N2 C3 C4 123.0(3) . . ? N2 C3 H3A 118.5 . . ? C4 C3 H3A 118.5 . . ? C3 C4 C5 118.6(2) . . ? C3 C4 H4A 120.7 . . ? C5 C4 H4A 120.7 . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C7 C6 C5 117.8(3) . . ? C7 C6 H6A 121.1 . . ? C5 C6 H6A 121.1 . . ? N2 C7 C6 123.4(2) . . ? N2 C7 N4 116.02(18) . . ? C6 C7 N4 120.5(2) . . ? N3 C8 C9 123.0(2) . . ? N3 C8 H8A 118.5 . . ? C9 C8 H8A 118.5 . . ? C10 C9 C8 119.0(2) . . ? C10 C9 H9A 120.5 . . ? C8 C9 H9A 120.5 . . ? C9 C10 C11 118.8(2) . . ? C9 C10 H10A 120.6 . . ? C11 C10 H10A 120.6 . . ? C10 C11 C12 118.6(2) . . ? C10 C11 H11A 120.7 . . ? C12 C11 H11A 120.7 . . ? N3 C12 C11 123.3(2) . . ? N3 C12 N4 117.42(18) . . ? C11 C12 N4 119.32(19) . . ? N5 C13 N6 126.14(18) . . ? N5 C13 N4 118.33(17) . . ? N6 C13 N4 115.53(17) . . ? N7 C14 N5 128.01(19) . . ? N7 C14 O1 119.15(19) . . ? N5 C14 O1 112.84(18) . . ? N6 C15 N7 127.85(18) . . ? N6 C15 O2 119.90(18) . . ? N7 C15 O2 112.25(17) . . ? C17 C16 C21 122.1(2) . . ? C17 C16 O1 117.7(2) . . ? C21 C16 O1 119.9(2) . . ? C16 C17 C18 119.1(2) . . ? C16 C17 H17A 120.4 . . ? C18 C17 H17A 120.4 . . ? C19 C18 C17 119.4(2) . . ? C19 C18 H18A 120.3 . . ? C17 C18 H18A 120.3 . . ? C20 C19 C18 120.5(2) . . ? C20 C19 H19A 119.7 . . ? C18 C19 H19A 119.7 . . ? C19 C20 C21 120.4(2) . . ? C19 C20 H20A 119.8 . . ? C21 C20 H20A 119.8 . . ? C16 C21 C20 118.4(2) . . ? C16 C21 H21A 120.8 . . ? C20 C21 H21A 120.8 . . ? C27 C22 C23 120.7(3) . . ? C27 C22 O2 113.7(3) . . ? C23 C22 O2 125.3(2) . . ? C22 C23 C24 118.6(3) . . ? C22 C23 H23A 120.7 . . ? C24 C23 H23A 120.7 . . ? C25 C24 C23 120.7(4) . . ? C25 C24 H24A 119.7 . . ? C23 C24 H24A 119.7 . . ? C26 C25 C24 119.3(3) . . ? C26 C25 H25A 120.4 . . ? C24 C25 H25A 120.4 . . ? C25 C26 C27 121.2(3) . . ? C25 C26 H26A 119.4 . . ? C27 C26 H26A 119.4 . . ? C22 C27 C26 119.4(4) . . ? C22 C27 H27A 120.3 . . ? C26 C27 H27A 120.3 . . ? Cl2 C28 Cl1 116.5(4) . . ? Cl2 C28 H28A 108.2 . . ? Cl1 C28 H28A 108.2 . . ? Cl2 C28 H28B 108.2 . . ? Cl1 C28 H28B 108.2 . . ? H28A C28 H28B 107.3 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.239 _refine_diff_density_min -0.959 _refine_diff_density_rms 0.101 data_14ch2cl2300ka _database_code_depnum_ccdc_archive 'CCDC 921063' #TrackingRef '17079_web_deposit_cif_file_2_OlivierRoubeau_1358848554.Cpd1-14ch2cl2300ka.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H36 Fe N14 O4 S2, 2(C H2 Cl2)' _chemical_formula_sum 'C54 H40 Cl4 Fe N14 O4 S2' _chemical_formula_weight 1210.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0020 0.0020 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' H H 0.0000 0.0000 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' N N -0.0031 0.0040 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' O O -0.0041 0.0074 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' S S 0.1206 0.1480 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Cl Cl 0.1408 0.1896 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Fe Fe 0.2064 0.9930 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3010(14) _cell_length_b 11.0444(15) _cell_length_c 13.2848(18) _cell_angle_alpha 86.033(2) _cell_angle_beta 80.447(2) _cell_angle_gamma 69.556(2) _cell_volume 1396.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 3026 _cell_measurement_theta_min 3.28 _cell_measurement_theta_max 29.24 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 0.749 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details 'SADABS Bruker AXS Madison WI US' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11351 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0825 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 28.97 _reflns_number_total 5637 _reflns_number_gt 4130 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.68a' _computing_data_reduction 'Bruker SAINT v7.68a' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogens were refined anisotropically. One of the phenyl ring carbons as well as the lattice dichloromethane molecule were refined with displacement parameters restraints. Hydrogens were placed geometrically on their carrier atom and refined with a riding model. ; _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^)+(0.1940P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5637 _refine_ls_number_parameters 358 _refine_ls_number_restraints 52 _refine_ls_R_factor_all 0.1071 _refine_ls_R_factor_gt 0.0918 _refine_ls_wR_factor_ref 0.2813 _refine_ls_wR_factor_gt 0.2586 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.5000 0.5000 0.5000 0.0409(3) Uani 1 2 d S . . S1 S 0.39777(15) 0.18532(14) 0.31995(11) 0.0749(4) Uani 1 1 d . . . O1 O 0.2086(3) 0.8892(3) 0.9068(3) 0.0610(8) Uani 1 1 d . . . O2 O 0.6347(3) 0.5974(3) 0.9377(2) 0.0529(7) Uani 1 1 d . . . N1 N 0.4593(4) 0.3682(4) 0.4172(3) 0.0572(9) Uani 1 1 d . . . N2 N 0.2791(3) 0.5592(3) 0.5757(2) 0.0486(8) Uani 1 1 d . . . N3 N 0.5308(4) 0.3573(3) 0.6261(2) 0.0466(7) Uani 1 1 d . . . N4 N 0.3590(3) 0.5137(3) 0.7341(2) 0.0392(7) Uani 1 1 d . . . N5 N 0.2821(3) 0.7089(3) 0.8168(2) 0.0454(7) Uani 1 1 d . . . N6 N 0.4992(3) 0.5475(3) 0.8380(2) 0.0415(7) Uani 1 1 d . . . N7 N 0.4227(3) 0.7412(3) 0.9299(2) 0.0463(7) Uani 1 1 d . . . C1 C 0.4317(4) 0.2935(4) 0.3783(3) 0.0495(9) Uani 1 1 d . . . C3 C 0.1731(5) 0.5953(5) 0.5203(4) 0.0655(12) Uani 1 1 d . . . H3A H 0.1954 0.5947 0.4496 0.079 Uiso 1 1 calc R . . C4 C 0.0366(5) 0.6322(6) 0.5614(4) 0.0695(13) Uani 1 1 d . . . H4A H -0.0331 0.6574 0.5200 0.083 Uiso 1 1 calc R . . C5 C 0.0032(5) 0.6318(6) 0.6655(4) 0.0755(15) Uani 1 1 d . . . H5A H -0.0901 0.6594 0.6962 0.091 Uiso 1 1 calc R . . C6 C 0.1094(4) 0.5899(5) 0.7244(3) 0.0599(11) Uani 1 1 d . . . H6A H 0.0892 0.5843 0.7951 0.072 Uiso 1 1 calc R . . C7 C 0.2454(4) 0.5569(4) 0.6762(3) 0.0416(8) Uani 1 1 d . . . C8 C 0.6212(5) 0.2362(4) 0.6099(4) 0.0606(11) Uani 1 1 d . . . H8A H 0.6696 0.2137 0.5445 0.073 Uiso 1 1 calc R . . C9 C 0.6448(5) 0.1450(4) 0.6858(4) 0.0654(12) Uani 1 1 d . . . H9A H 0.7090 0.0623 0.6725 0.079 Uiso 1 1 calc R . . C10 C 0.5719(5) 0.1774(4) 0.7827(4) 0.0625(11) Uani 1 1 d . . . H10A H 0.5882 0.1180 0.8364 0.075 Uiso 1 1 calc R . . C11 C 0.4752(5) 0.2987(4) 0.7979(3) 0.0526(9) Uani 1 1 d . . . H11A H 0.4213 0.3222 0.8616 0.063 Uiso 1 1 calc R . . C12 C 0.4590(4) 0.3851(3) 0.7181(3) 0.0407(8) Uani 1 1 d . . . C13 C 0.3789(4) 0.5946(3) 0.7984(2) 0.0370(7) Uani 1 1 d . . . C14 C 0.3105(4) 0.7746(4) 0.8842(3) 0.0448(8) Uani 1 1 d . . . C15 C 0.5142(4) 0.6284(4) 0.8985(3) 0.0407(8) Uani 1 1 d . . . C16 C 0.2246(4) 0.9702(4) 0.9772(3) 0.0502(9) Uani 1 1 d . . . C17 C 0.1340(4) 0.9919(4) 1.0668(4) 0.0571(10) Uani 1 1 d . . . H17A H 0.0713 0.9475 1.0829 0.069 Uiso 1 1 calc R . . C18 C 0.1374(5) 1.0818(5) 1.1338(3) 0.0619(11) Uani 1 1 d . . . H18A H 0.0768 1.0983 1.1954 0.074 Uiso 1 1 calc R . . C19 C 0.2319(5) 1.1466(4) 1.1077(4) 0.0601(11) Uani 1 1 d . . . H19A H 0.2333 1.2083 1.1514 0.072 Uiso 1 1 calc R . . C20 C 0.3231(5) 1.1204(4) 1.0181(4) 0.0601(11) Uani 1 1 d . . . H20A H 0.3886 1.1619 1.0022 0.072 Uiso 1 1 calc R . . C21 C 0.3182(5) 1.0326(4) 0.9515(4) 0.0577(10) Uani 1 1 d . . . H21A H 0.3782 1.0163 0.8896 0.069 Uiso 1 1 calc R . . C22 C 0.7542(4) 0.4943(4) 0.9047(3) 0.0509(9) Uani 1 1 d . . . C23 C 0.7936(6) 0.4475(7) 0.8056(5) 0.096(2) Uani 1 1 d U . . H23A H 0.7355 0.4808 0.7563 0.115 Uiso 1 1 calc R . . C24 C 0.9210(6) 0.3506(8) 0.7826(6) 0.104(2) Uani 1 1 d U . . H24A H 0.9507 0.3200 0.7162 0.125 Uiso 1 1 calc R . . C25 C 1.0041(7) 0.2989(7) 0.8547(6) 0.1022(19) Uani 1 1 d U . . H25A H 1.0875 0.2303 0.8390 0.123 Uiso 1 1 calc R . . C26 C 0.9650(7) 0.3475(8) 0.9492(6) 0.114(2) Uani 1 1 d U . . H26A H 1.0245 0.3142 0.9976 0.136 Uiso 1 1 calc R . . C27 C 0.8386(6) 0.4458(7) 0.9768(4) 0.0916(19) Uani 1 1 d U . . H27A H 0.8124 0.4778 1.0428 0.110 Uiso 1 1 calc R . . Cl2 Cl 0.7327(3) 0.8080(4) 0.3719(3) 0.1864(14) Uani 1 1 d U . . Cl1 Cl 0.8751(4) 0.9783(4) 0.4132(4) 0.2261(19) Uani 1 1 d U . . C28 C 0.7186(12) 0.9445(13) 0.4148(9) 0.169(3) Uani 1 1 d U . . H28A H 0.6712 0.9509 0.4847 0.202 Uiso 1 1 calc R . . H28B H 0.6582 1.0117 0.3756 0.202 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 0.0484(5) 0.0416(5) 0.0345(4) -0.0052(3) -0.0091(3) -0.0153(3) S1 0.0852(9) 0.0715(9) 0.0847(9) -0.0192(7) -0.0263(7) -0.0383(7) O1 0.0443(15) 0.0550(17) 0.080(2) -0.0332(15) -0.0201(14) -0.0013(13) O2 0.0484(15) 0.0554(17) 0.0548(16) -0.0168(13) -0.0192(12) -0.0095(12) N1 0.076(2) 0.060(2) 0.0454(18) -0.0098(16) -0.0094(17) -0.0336(19) N2 0.0487(17) 0.058(2) 0.0421(17) -0.0044(14) -0.0149(13) -0.0178(15) N3 0.0562(18) 0.0365(16) 0.0434(17) -0.0071(13) -0.0076(14) -0.0101(14) N4 0.0447(15) 0.0392(16) 0.0344(14) -0.0066(12) -0.0098(12) -0.0122(13) N5 0.0402(16) 0.0474(18) 0.0478(17) -0.0130(14) -0.0114(13) -0.0095(13) N6 0.0435(16) 0.0405(16) 0.0392(15) -0.0063(12) -0.0100(12) -0.0100(13) N7 0.0415(16) 0.0492(18) 0.0473(17) -0.0133(14) -0.0106(13) -0.0101(14) C1 0.056(2) 0.054(2) 0.041(2) -0.0007(17) -0.0109(16) -0.0204(18) C3 0.063(3) 0.079(3) 0.056(3) 0.001(2) -0.026(2) -0.019(2) C4 0.050(2) 0.084(3) 0.074(3) -0.009(3) -0.027(2) -0.014(2) C5 0.046(2) 0.099(4) 0.079(3) -0.029(3) -0.012(2) -0.015(2) C6 0.046(2) 0.081(3) 0.051(2) -0.017(2) -0.0054(17) -0.017(2) C7 0.0438(18) 0.0400(18) 0.0430(18) -0.0076(14) -0.0134(15) -0.0124(15) C8 0.070(3) 0.044(2) 0.055(2) -0.0090(19) -0.001(2) -0.0062(19) C9 0.069(3) 0.040(2) 0.075(3) -0.002(2) -0.011(2) -0.003(2) C10 0.075(3) 0.047(2) 0.065(3) 0.012(2) -0.021(2) -0.017(2) C11 0.064(2) 0.048(2) 0.044(2) 0.0011(17) -0.0075(17) -0.0176(19) C12 0.0480(19) 0.0386(19) 0.0370(17) -0.0053(14) -0.0119(14) -0.0134(15) C13 0.0412(17) 0.0386(18) 0.0321(16) -0.0046(13) -0.0051(13) -0.0143(14) C14 0.0417(18) 0.043(2) 0.049(2) -0.0146(16) -0.0060(15) -0.0109(15) C15 0.0405(17) 0.0447(19) 0.0387(18) -0.0053(14) -0.0119(14) -0.0135(15) C16 0.0443(19) 0.040(2) 0.065(2) -0.0161(17) -0.0201(18) -0.0052(15) C17 0.043(2) 0.057(3) 0.070(3) -0.007(2) -0.0113(19) -0.0117(18) C18 0.056(2) 0.068(3) 0.052(2) -0.012(2) -0.0088(19) -0.008(2) C19 0.066(3) 0.044(2) 0.069(3) -0.014(2) -0.031(2) -0.0055(19) C20 0.061(2) 0.048(2) 0.077(3) -0.002(2) -0.022(2) -0.021(2) C21 0.052(2) 0.058(3) 0.063(3) -0.013(2) -0.0096(19) -0.0149(19) C22 0.0421(19) 0.051(2) 0.061(2) 0.0032(18) -0.0171(17) -0.0131(16) C23 0.058(3) 0.122(5) 0.086(4) -0.045(3) -0.025(2) 0.009(3) C24 0.062(3) 0.114(5) 0.115(4) -0.044(4) -0.018(3) 0.007(3) C25 0.067(3) 0.086(4) 0.125(4) 0.004(3) -0.013(3) 0.008(3) C26 0.079(3) 0.127(5) 0.091(3) 0.037(3) -0.023(3) 0.017(3) C27 0.064(3) 0.123(5) 0.062(3) 0.019(3) -0.020(2) 0.000(3) Cl2 0.142(2) 0.271(4) 0.165(3) -0.064(3) -0.0078(19) -0.090(3) Cl1 0.182(3) 0.204(4) 0.296(5) -0.073(4) -0.016(3) -0.067(3) C28 0.134(5) 0.205(6) 0.149(7) -0.030(6) -0.048(6) -0.017(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 Fe1 N1 2.075(4) . ? Fe1 N1 2.075(4) 2_666 ? Fe1 N3 2.203(3) 2_666 ? Fe1 N3 2.203(3) . ? Fe1 N2 2.216(3) . ? Fe1 N2 2.216(3) 2_666 ? S1 C1 1.631(4) . ? O1 C14 1.347(5) . ? O1 C16 1.405(5) . ? O2 C15 1.350(4) . ? O2 C22 1.384(5) . ? N1 C1 1.140(5) . ? N2 C7 1.324(5) . ? N2 C3 1.347(5) . ? N3 C12 1.314(5) . ? N3 C8 1.344(5) . ? N4 C13 1.364(4) . ? N4 C7 1.430(4) . ? N4 C12 1.440(5) . ? N5 C13 1.316(5) . ? N5 C14 1.319(5) . ? N6 C15 1.306(5) . ? N6 C13 1.346(4) . ? N7 C15 1.318(5) . ? N7 C14 1.321(5) . ? C3 C4 1.348(7) . ? C3 H3A 0.9300 . ? C4 C5 1.369(7) . ? C4 H4A 0.9300 . ? C5 C6 1.380(7) . ? C5 H5A 0.9300 . ? C6 C7 1.373(6) . ? C6 H6A 0.9300 . ? C8 C9 1.364(7) . ? C8 H8A 0.9300 . ? C9 C10 1.380(7) . ? C9 H9A 0.9300 . ? C10 C11 1.366(6) . ? C10 H10A 0.9300 . ? C11 C12 1.368(5) . ? C11 H11A 0.9300 . ? C16 C21 1.358(6) . ? C16 C17 1.364(6) . ? C17 C18 1.391(6) . ? C17 H17A 0.9300 . ? C18 C19 1.386(7) . ? C18 H18A 0.9300 . ? C19 C20 1.367(7) . ? C19 H19A 0.9300 . ? C20 C21 1.376(6) . ? C20 H20A 0.9300 . ? C21 H21A 0.9300 . ? C22 C27 1.356(6) . ? C22 C23 1.392(7) . ? C23 C24 1.376(8) . ? C23 H23A 0.9300 . ? C24 C25 1.353(10) . ? C24 H24A 0.9300 . ? C25 C26 1.342(10) . ? C25 H25A 0.9300 . ? C26 C27 1.384(9) . ? C26 H26A 0.9300 . ? C27 H27A 0.9300 . ? Cl2 C28 1.598(12) . ? Cl1 C28 1.774(13) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 180.00(13) . 2_666 ? N1 Fe1 N3 92.06(13) . 2_666 ? N1 Fe1 N3 87.94(13) 2_666 2_666 ? N1 Fe1 N3 87.94(13) . . ? N1 Fe1 N3 92.06(13) 2_666 . ? N3 Fe1 N3 179.999(1) 2_666 . ? N1 Fe1 N2 88.12(14) . . ? N1 Fe1 N2 91.88(14) 2_666 . ? N3 Fe1 N2 97.58(12) 2_666 . ? N3 Fe1 N2 82.42(12) . . ? N1 Fe1 N2 91.88(14) . 2_666 ? N1 Fe1 N2 88.12(14) 2_666 2_666 ? N3 Fe1 N2 82.42(12) 2_666 2_666 ? N3 Fe1 N2 97.58(12) . 2_666 ? N2 Fe1 N2 180.0 . 2_666 ? C14 O1 C16 119.4(3) . . ? C15 O2 C22 123.6(3) . . ? C1 N1 Fe1 174.9(4) . . ? C7 N2 C3 117.2(4) . . ? C7 N2 Fe1 122.0(2) . . ? C3 N2 Fe1 120.8(3) . . ? C12 N3 C8 117.6(3) . . ? C12 N3 Fe1 122.0(2) . . ? C8 N3 Fe1 120.4(3) . . ? C13 N4 C7 121.3(3) . . ? C13 N4 C12 119.9(3) . . ? C7 N4 C12 118.7(3) . . ? C13 N5 C14 112.9(3) . . ? C15 N6 C13 113.2(3) . . ? C15 N7 C14 111.7(3) . . ? N1 C1 S1 177.9(4) . . ? N2 C3 C4 123.9(5) . . ? N2 C3 H3A 118.1 . . ? C4 C3 H3A 118.1 . . ? C3 C4 C5 118.3(4) . . ? C3 C4 H4A 120.8 . . ? C5 C4 H4A 120.8 . . ? C4 C5 C6 119.3(4) . . ? C4 C5 H5A 120.4 . . ? C6 C5 H5A 120.4 . . ? C7 C6 C5 118.4(4) . . ? C7 C6 H6A 120.8 . . ? C5 C6 H6A 120.8 . . ? N2 C7 C6 122.8(3) . . ? N2 C7 N4 116.7(3) . . ? C6 C7 N4 120.5(3) . . ? N3 C8 C9 122.5(4) . . ? N3 C8 H8A 118.7 . . ? C9 C8 H8A 118.7 . . ? C8 C9 C10 119.0(4) . . ? C8 C9 H9A 120.5 . . ? C10 C9 H9A 120.5 . . ? C11 C10 C9 118.4(4) . . ? C11 C10 H10A 120.8 . . ? C9 C10 H10A 120.8 . . ? C10 C11 C12 119.0(4) . . ? C10 C11 H11A 120.5 . . ? C12 C11 H11A 120.5 . . ? N3 C12 C11 123.4(4) . . ? N3 C12 N4 117.4(3) . . ? C11 C12 N4 119.2(3) . . ? N5 C13 N6 125.8(3) . . ? N5 C13 N4 118.9(3) . . ? N6 C13 N4 115.3(3) . . ? N5 C14 N7 128.3(3) . . ? N5 C14 O1 113.0(3) . . ? N7 C14 O1 118.7(3) . . ? N6 C15 N7 127.8(3) . . ? N6 C15 O2 119.4(3) . . ? N7 C15 O2 112.7(3) . . ? C21 C16 C17 122.3(4) . . ? C21 C16 O1 120.3(4) . . ? C17 C16 O1 117.1(4) . . ? C16 C17 C18 118.6(4) . . ? C16 C17 H17A 120.7 . . ? C18 C17 H17A 120.7 . . ? C19 C18 C17 119.4(4) . . ? C19 C18 H18A 120.3 . . ? C17 C18 H18A 120.3 . . ? C20 C19 C18 120.4(4) . . ? C20 C19 H19A 119.8 . . ? C18 C19 H19A 119.8 . . ? C19 C20 C21 120.1(4) . . ? C19 C20 H20A 120.0 . . ? C21 C20 H20A 120.0 . . ? C16 C21 C20 119.2(4) . . ? C16 C21 H21A 120.4 . . ? C20 C21 H21A 120.4 . . ? C27 C22 O2 113.8(4) . . ? C27 C22 C23 121.1(5) . . ? O2 C22 C23 124.9(4) . . ? C24 C23 C22 118.0(5) . . ? C24 C23 H23A 121.0 . . ? C22 C23 H23A 121.0 . . ? C25 C24 C23 121.3(7) . . ? C25 C24 H24A 119.4 . . ? C23 C24 H24A 119.4 . . ? C26 C25 C24 119.4(6) . . ? C26 C25 H25A 120.3 . . ? C24 C25 H25A 120.3 . . ? C25 C26 C27 121.9(6) . . ? C25 C26 H26A 119.0 . . ? C27 C26 H26A 119.0 . . ? C22 C27 C26 118.1(6) . . ? C22 C27 H27A 120.9 . . ? C26 C27 H27A 120.9 . . ? Cl2 C28 Cl1 117.6(7) . . ? Cl2 C28 H28A 107.9 . . ? Cl1 C28 H28A 107.9 . . ? Cl2 C28 H28B 107.9 . . ? Cl1 C28 H28B 107.9 . . ? H28A C28 H28B 107.2 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.97 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.304 _refine_diff_density_min -0.711 _refine_diff_density_rms 0.117 data_17CH2CL2 _database_code_depnum_ccdc_archive 'CCDC 921064' #TrackingRef '17080_web_deposit_cif_file_3_OlivierRoubeau_1358848554.Cpd2-032PG17CH2CL2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H36 Fe N14 O4 Se2, 4(C H2 Cl2), 4(C H4 O)' _chemical_formula_sum 'C60 H60 Cl8 Fe N14 O8 Se2' _chemical_formula_weight 1602.59 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.642(2) _cell_length_b 32.287(6) _cell_length_c 13.175(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.243(12) _cell_angle_gamma 90.00 _cell_volume 3426.4(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8026 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 26.15 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 1.657 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.90 _exptl_absorpt_process_details 'SADABS Bruker AXS Madison WI US' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'multilayer monochromator ImuS' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II QUAZAR' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23597 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.35 _reflns_number_total 6249 _reflns_number_gt 5064 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogens were refined anisotropically. The lattice dichloromethane molecules were disordered over two positions, with relative occupation of 0.57:0.43 (C1S:C2S) and 0.56:0.44 (C3S:C4S). The methanol lattice molecules also showed some disorder but did not require splitting. All these lattice solvent molecules were refined with displacement parameters restraints (SIMU/DELU). The C-Cl distances were also restrained to be similar (SADI). Hydrogens were placed geometrically on their carrier atom and refined with a riding model, except for the hydroxyl hydrogens on O1S and O2S that were refined freely with a soft distance restrain. At the end of the refinement a residual 1.9 electron peak remained close to the heaviest atom Se1, that could not be integrated in the structural model. ; _vrf_PLAT415_17CH2CL2 ; PROBLEM: Short Inter D-H..H-X H1S .. H13 .. 1.83 Ang. RESPONSE: Both H1S and H13 pertain to lattice methanol molecules, that show some disorder and were refined with displacement parameter restrains. H1S was refined freely with a soft distance restrain. The short H H contact may thus be partly due to non-ideal hydrogen positions. Nevertheless, the two methanol molecules are hydrogen bonded through H1S so that such short contact may also be a consequence of the closeness of the two molecules. ; _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^)+(0.1140P)^2^+10.3463P] 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 6249 _refine_ls_number_parameters 483 _refine_ls_number_restraints 94 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.1978 _refine_ls_wR_factor_gt 0.1882 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.107 _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 0.5000 0.5000 0.5000 0.0130(2) Uani 1 2 d S . . Se1 Se 0.44066(7) 0.590929(16) 0.78054(4) 0.0253(2) Uani 1 1 d . . . O1 O 0.3492(6) 0.30535(11) 0.3062(3) 0.0327(10) Uani 1 1 d . . . O2 O 0.0189(5) 0.39297(11) 0.0522(3) 0.0235(8) Uani 1 1 d . . . N1 N 0.4831(5) 0.53453(12) 0.6160(3) 0.0173(9) Uani 1 1 d . . . N2 N 0.4549(5) 0.45059(12) 0.5755(3) 0.0161(9) Uani 1 1 d . . . N3 N 0.2526(5) 0.50477(11) 0.4258(3) 0.0140(8) Uani 1 1 d . . . N4 N 0.2337(5) 0.43191(11) 0.4147(3) 0.0132(8) Uani 1 1 d . . . N5 N 0.2953(6) 0.36743(12) 0.3622(3) 0.0197(9) Uani 1 1 d . . . N6 N 0.1751(6) 0.34840(12) 0.1752(3) 0.0203(9) Uani 1 1 d . . . N7 N 0.1199(5) 0.41519(12) 0.2320(3) 0.0182(9) Uani 1 1 d . . . C1 C 0.4635(6) 0.55646(14) 0.6801(4) 0.0185(10) Uani 1 1 d . . . C2 C 0.5431(7) 0.44431(15) 0.6815(4) 0.0197(11) Uani 1 1 d . . . H2A H 0.6259 0.4640 0.7189 0.024 Uiso 1 1 calc R . . C3 C 0.5195(7) 0.41086(16) 0.7385(4) 0.0235(11) Uani 1 1 d . . . H3A H 0.5861 0.4075 0.8133 0.028 Uiso 1 1 calc R . . C4 C 0.3988(7) 0.38215(16) 0.6867(4) 0.0241(12) Uani 1 1 d . . . H4A H 0.3825 0.3584 0.7241 0.029 Uiso 1 1 calc R . . C5 C 0.3015(6) 0.38898(15) 0.5780(4) 0.0181(10) Uani 1 1 d . . . H5A H 0.2140 0.3705 0.5405 0.022 Uiso 1 1 calc R . . C6 C 0.3339(6) 0.42310(14) 0.5252(4) 0.0158(10) Uani 1 1 d . . . C7 C 0.1761(6) 0.54216(15) 0.4126(4) 0.0183(10) Uani 1 1 d . . . H7A H 0.2427 0.5662 0.4374 0.022 Uiso 1 1 calc R . . C8 C 0.0082(7) 0.54697(16) 0.3656(4) 0.0242(11) Uani 1 1 d . . . H8A H -0.0395 0.5739 0.3556 0.029 Uiso 1 1 calc R . . C9 C -0.0931(7) 0.51202(17) 0.3324(4) 0.0238(11) Uani 1 1 d . . . H9A H -0.2103 0.5146 0.2995 0.029 Uiso 1 1 calc R . . C10 C -0.0179(6) 0.47371(15) 0.3485(4) 0.0203(11) Uani 1 1 d . . . H10A H -0.0829 0.4492 0.3288 0.024 Uiso 1 1 calc R . . C11 C 0.1527(6) 0.47138(14) 0.3937(4) 0.0148(10) Uani 1 1 d . . . C12 C 0.2130(6) 0.40362(14) 0.3332(4) 0.0155(10) Uani 1 1 d . . . C13 C 0.2677(7) 0.34197(14) 0.2776(4) 0.0204(11) Uani 1 1 d . . . C14 C 0.1066(6) 0.38601(15) 0.1584(4) 0.0176(10) Uani 1 1 d . . . C15 C 0.3268(8) 0.27715(16) 0.2198(5) 0.0303(13) Uani 1 1 d . . . C16 C 0.2152(9) 0.24550(17) 0.2046(5) 0.0393(16) Uani 1 1 d . . . H16A H 0.1519 0.2429 0.2500 0.047 Uiso 1 1 calc R . . C17 C 0.1962(10) 0.21724(18) 0.1217(6) 0.0464(18) Uani 1 1 d . . . H17A H 0.1181 0.1954 0.1094 0.056 Uiso 1 1 calc R . . C18 C 0.2902(9) 0.22075(17) 0.0568(5) 0.0388(15) Uani 1 1 d . . . H18A H 0.2762 0.2015 -0.0004 0.047 Uiso 1 1 calc R . . C19 C 0.4044(9) 0.25233(18) 0.0755(6) 0.0393(15) Uani 1 1 d . . . H19A H 0.4701 0.2546 0.0314 0.047 Uiso 1 1 calc R . . C20 C 0.4243(9) 0.28088(17) 0.1582(5) 0.0380(15) Uani 1 1 d . . . H20A H 0.5038 0.3025 0.1718 0.046 Uiso 1 1 calc R . . C21 C -0.0777(7) 0.42880(16) 0.0163(4) 0.0227(11) Uani 1 1 d . . . C22 C -0.0578(7) 0.44986(18) -0.0697(4) 0.0278(12) Uani 1 1 d . . . H22A H 0.0202 0.4407 -0.1004 0.033 Uiso 1 1 calc R . . C23 C -0.1545(8) 0.48464(17) -0.1099(4) 0.0309(13) Uani 1 1 d . . . H23A H -0.1409 0.4999 -0.1678 0.037 Uiso 1 1 calc R . . C24 C -0.2696(8) 0.49735(18) -0.0670(5) 0.0328(14) Uani 1 1 d . . . H24A H -0.3355 0.5212 -0.0954 0.039 Uiso 1 1 calc R . . C25 C -0.2894(7) 0.47516(19) 0.0181(5) 0.0342(14) Uani 1 1 d . . . H25A H -0.3695 0.4839 0.0475 0.041 Uiso 1 1 calc R . . C26 C -0.1941(7) 0.44056(17) 0.0603(4) 0.0245(12) Uani 1 1 d . . . H26A H -0.2079 0.4252 0.1180 0.029 Uiso 1 1 calc R . . Cl1 Cl 0.1315(6) 0.35458(17) 0.8379(4) 0.0507(11) Uani 0.570(6) 1 d PDU A 1 Cl2 Cl 0.4889(4) 0.35036(9) 0.9630(2) 0.0441(10) Uani 0.570(6) 1 d PDU A 1 C1S C 0.2960(14) 0.3668(5) 0.9606(10) 0.050(3) Uani 0.570(6) 1 d PDU A 1 H1SA H 0.2990 0.3971 0.9716 0.060 Uiso 0.570(6) 1 calc PR A 1 H1SB H 0.2738 0.3537 1.0220 0.060 Uiso 0.570(6) 1 calc PR A 1 Cl3 Cl 0.3357(10) 0.3974(3) 0.9296(6) 0.110(3) Uani 0.430(6) 1 d PDU A 2 Cl4 Cl 0.0525(13) 0.3447(3) 0.8170(7) 0.084(2) Uani 0.430(6) 1 d PDU A 2 C2S C 0.246(2) 0.3480(6) 0.9262(17) 0.091(6) Uani 0.430(6) 1 d PDU A 2 H2SA H 0.2294 0.3430 0.9958 0.109 Uiso 0.430(6) 1 calc PR A 2 H2SB H 0.3215 0.3265 0.9177 0.109 Uiso 0.430(6) 1 calc PR A 2 Cl5 Cl 0.8207(5) 0.27982(15) 1.0715(4) 0.0791(17) Uani 0.557(7) 1 d PDU B 1 Cl6 Cl 0.7539(10) 0.2864(2) 0.8400(4) 0.104(2) Uani 0.557(7) 1 d PDU B 1 C3S C 0.904(2) 0.2916(5) 0.9710(9) 0.064(4) Uani 0.557(7) 1 d PDU B 1 H3SA H 0.9463 0.3204 0.9814 0.077 Uiso 0.557(7) 1 calc PR B 1 H3SB H 0.9978 0.2728 0.9789 0.077 Uiso 0.557(7) 1 calc PR B 1 Cl7 Cl 0.7491(11) 0.3239(3) 1.0838(8) 0.141(4) Uani 0.443(7) 1 d PDU B 2 Cl8 Cl 0.6645(14) 0.2855(3) 0.8718(8) 0.121(3) Uani 0.443(7) 1 d PDU B 2 C4S C 0.817(3) 0.3109(9) 0.9774(15) 0.096(7) Uani 0.443(7) 1 d PDU B 2 H4SA H 0.8500 0.3365 0.9489 0.115 Uiso 0.443(7) 1 calc PR B 2 H4SB H 0.9161 0.2929 1.0060 0.115 Uiso 0.443(7) 1 calc PR B 2 O1S O 0.9315(9) 0.3560(3) 0.4209(6) 0.087(2) Uani 1 1 d DU . . H1S H 0.874(13) 0.358(3) 0.472(7) 0.105 Uiso 1 1 d D . . C5S C 0.8928(10) 0.3279(3) 0.3533(10) 0.080(3) Uani 1 1 d DU . . H9 H 0.8242 0.3390 0.2820 0.120 Uiso 1 1 calc R . . H10 H 0.8298 0.3068 0.3755 0.120 Uiso 1 1 calc R . . H11 H 0.9934 0.3154 0.3488 0.120 Uiso 1 1 calc R . . O2S O 0.6687(9) 0.3656(2) 0.4988(6) 0.0809(19) Uani 1 1 d DU . . H2S H 0.562(7) 0.370(3) 0.439(6) 0.097 Uiso 1 1 d D . . C6S C 0.7364(14) 0.3382(3) 0.5738(7) 0.083(3) Uani 1 1 d DU . . H12 H 0.6969 0.3422 0.6341 0.125 Uiso 1 1 calc R . . H13 H 0.8574 0.3413 0.6007 0.125 Uiso 1 1 calc R . . H14 H 0.7061 0.3104 0.5433 0.125 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 0.0177(5) 0.0074(5) 0.0168(5) -0.0013(3) 0.0099(4) -0.0009(4) Se1 0.0344(4) 0.0199(3) 0.0303(3) -0.0097(2) 0.0221(3) -0.0045(2) O1 0.061(3) 0.0150(18) 0.022(2) -0.0039(15) 0.0149(19) 0.0006(18) O2 0.031(2) 0.0219(19) 0.0185(19) -0.0013(14) 0.0100(16) 0.0020(16) N1 0.022(2) 0.0124(19) 0.021(2) 0.0007(16) 0.0122(18) -0.0033(16) N2 0.023(2) 0.0106(19) 0.019(2) -0.0039(15) 0.0128(18) -0.0011(16) N3 0.019(2) 0.0090(18) 0.017(2) 0.0002(15) 0.0103(17) -0.0006(15) N4 0.018(2) 0.0066(18) 0.017(2) 0.0002(15) 0.0080(16) -0.0009(15) N5 0.034(3) 0.0073(19) 0.020(2) -0.0002(16) 0.0115(19) 0.0006(17) N6 0.030(2) 0.012(2) 0.022(2) -0.0027(16) 0.0138(19) -0.0039(17) N7 0.024(2) 0.011(2) 0.021(2) -0.0023(16) 0.0108(18) -0.0037(16) C1 0.024(3) 0.011(2) 0.026(3) -0.0022(19) 0.015(2) -0.0053(19) C2 0.026(3) 0.016(2) 0.019(3) 0.0000(19) 0.011(2) -0.002(2) C3 0.030(3) 0.024(3) 0.017(3) 0.004(2) 0.009(2) 0.000(2) C4 0.040(3) 0.016(2) 0.022(3) 0.004(2) 0.018(2) 0.000(2) C5 0.022(3) 0.013(2) 0.023(3) 0.0008(19) 0.012(2) -0.0017(19) C6 0.019(2) 0.013(2) 0.018(2) -0.0031(18) 0.009(2) 0.0000(19) C7 0.024(3) 0.011(2) 0.024(3) -0.0012(19) 0.014(2) 0.0012(19) C8 0.028(3) 0.019(3) 0.029(3) -0.002(2) 0.015(2) 0.003(2) C9 0.020(3) 0.026(3) 0.028(3) 0.000(2) 0.011(2) 0.004(2) C10 0.022(3) 0.019(2) 0.026(3) -0.002(2) 0.015(2) -0.001(2) C11 0.023(3) 0.012(2) 0.013(2) -0.0003(17) 0.011(2) 0.0003(19) C12 0.017(2) 0.010(2) 0.023(3) 0.0012(18) 0.011(2) -0.0014(18) C13 0.034(3) 0.007(2) 0.025(3) 0.0018(19) 0.016(2) 0.000(2) C14 0.023(3) 0.017(2) 0.016(2) -0.0018(19) 0.011(2) -0.006(2) C15 0.053(4) 0.010(2) 0.031(3) -0.002(2) 0.018(3) 0.003(2) C16 0.065(5) 0.018(3) 0.048(4) -0.005(3) 0.037(4) -0.004(3) C17 0.073(5) 0.015(3) 0.065(5) -0.011(3) 0.041(4) -0.013(3) C18 0.068(5) 0.014(3) 0.043(4) -0.010(2) 0.031(3) -0.002(3) C19 0.059(4) 0.022(3) 0.049(4) -0.004(3) 0.034(3) 0.003(3) C20 0.055(4) 0.017(3) 0.049(4) -0.006(3) 0.029(3) -0.005(3) C21 0.025(3) 0.021(3) 0.020(3) -0.002(2) 0.007(2) -0.002(2) C22 0.030(3) 0.033(3) 0.020(3) -0.006(2) 0.010(2) -0.016(2) C23 0.041(3) 0.024(3) 0.019(3) 0.003(2) 0.000(2) -0.011(3) C24 0.031(3) 0.026(3) 0.028(3) -0.003(2) -0.005(3) 0.002(2) C25 0.026(3) 0.040(3) 0.032(3) -0.004(3) 0.005(2) 0.006(3) C26 0.021(3) 0.033(3) 0.021(3) -0.001(2) 0.009(2) -0.004(2) Cl1 0.055(3) 0.063(3) 0.041(2) -0.0127(18) 0.025(2) 0.000(2) Cl2 0.055(2) 0.0451(18) 0.0394(17) 0.0095(12) 0.0253(14) 0.0056(13) C1S 0.058(8) 0.045(8) 0.047(9) -0.005(6) 0.019(6) -0.001(6) Cl3 0.100(5) 0.166(7) 0.082(4) -0.049(4) 0.053(4) -0.028(4) Cl4 0.112(7) 0.071(5) 0.078(5) -0.024(3) 0.044(5) -0.001(4) C2S 0.112(14) 0.126(14) 0.050(13) 0.014(15) 0.047(7) 0.028(13) Cl5 0.053(2) 0.087(3) 0.098(3) 0.011(2) 0.028(2) -0.010(2) Cl6 0.108(5) 0.109(5) 0.065(3) -0.008(3) -0.003(3) -0.014(4) C3S 0.077(12) 0.040(8) 0.066(8) -0.008(7) 0.014(6) -0.015(7) Cl7 0.119(5) 0.151(7) 0.183(6) -0.057(5) 0.092(5) -0.055(5) Cl8 0.119(6) 0.087(5) 0.122(5) 0.003(4) 0.003(5) -0.041(5) C4S 0.079(18) 0.10(2) 0.093(15) -0.011(13) 0.015(9) -0.008(14) O1S 0.058(4) 0.107(6) 0.096(5) 0.004(4) 0.027(4) 0.011(4) C5S 0.031(4) 0.047(4) 0.150(8) 0.010(5) 0.017(4) 0.007(3) O2S 0.075(5) 0.067(4) 0.085(5) 0.004(3) 0.010(4) 0.000(3) C6S 0.130(6) 0.067(5) 0.050(4) 0.017(4) 0.030(4) 0.073(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 Fe1 N1 1.939(4) 3_666 ? Fe1 N1 1.939(4) . ? Fe1 N2 1.992(4) . ? Fe1 N2 1.992(4) 3_666 ? Fe1 N3 2.009(4) 3_666 ? Fe1 N3 2.009(4) . ? Se1 C1 1.794(5) . ? O1 C13 1.358(6) . ? O1 C15 1.415(6) . ? O2 C14 1.346(6) . ? O2 C21 1.405(6) . ? N1 C1 1.161(6) . ? N2 C2 1.342(7) . ? N2 C6 1.348(6) . ? N3 C11 1.350(6) . ? N3 C7 1.357(6) . ? N4 C12 1.372(6) . ? N4 C6 1.427(6) . ? N4 C11 1.432(6) . ? N5 C13 1.335(6) . ? N5 C12 1.349(6) . ? N6 C13 1.312(7) . ? N6 C14 1.334(6) . ? N7 C14 1.327(6) . ? N7 C12 1.337(7) . ? C2 C3 1.373(7) . ? C2 H2A 0.9500 . ? C3 C4 1.377(8) . ? C3 H3A 0.9500 . ? C4 C5 1.391(7) . ? C4 H4A 0.9500 . ? C5 C6 1.385(7) . ? C5 H5A 0.9500 . ? C7 C8 1.364(8) . ? C7 H7A 0.9500 . ? C8 C9 1.398(8) . ? C8 H8A 0.9500 . ? C9 C10 1.377(7) . ? C9 H9A 0.9500 . ? C10 C11 1.378(7) . ? C10 H10A 0.9500 . ? C15 C16 1.369(9) . ? C15 C20 1.370(9) . ? C16 C17 1.387(9) . ? C16 H16A 0.9500 . ? C17 C18 1.381(9) . ? C17 H17A 0.9500 . ? C18 C19 1.378(9) . ? C18 H18A 0.9500 . ? C19 C20 1.390(8) . ? C19 H19A 0.9500 . ? C20 H20A 0.9500 . ? C21 C26 1.383(8) . ? C21 C22 1.385(7) . ? C22 C23 1.385(8) . ? C22 H22A 0.9500 . ? C23 C24 1.372(9) . ? C23 H23A 0.9500 . ? C24 C25 1.393(9) . ? C24 H24A 0.9500 . ? C25 C26 1.380(8) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? Cl1 C1S 1.767(11) . ? Cl2 C1S 1.739(12) . ? C1S H1SA 0.9900 . ? C1S H1SB 0.9900 . ? Cl3 C2S 1.768(15) . ? Cl4 C2S 1.768(15) . ? C2S H2SA 0.9900 . ? C2S H2SB 0.9900 . ? Cl5 C3S 1.760(13) . ? Cl6 C3S 1.750(12) . ? C3S H3SA 0.9900 . ? C3S H3SB 0.9900 . ? Cl7 C4S 1.756(15) . ? Cl8 C4S 1.737(14) . ? C4S H4SA 0.9900 . ? C4S H4SB 0.9900 . ? O1S C5S 1.231(10) . ? O1S H1S 0.97(2) . ? C5S H9 0.9800 . ? C5S H10 0.9800 . ? C5S H11 0.9800 . ? O2S C6S 1.298(9) . ? O2S H2S 0.98(2) . ? C6S H12 0.9800 . ? C6S H13 0.9800 . ? C6S H14 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 180.000(2) 3_666 . ? N1 Fe1 N2 90.99(15) 3_666 . ? N1 Fe1 N2 89.01(15) . . ? N1 Fe1 N2 89.01(15) 3_666 3_666 ? N1 Fe1 N2 90.99(15) . 3_666 ? N2 Fe1 N2 180.00(13) . 3_666 ? N1 Fe1 N3 88.21(17) 3_666 3_666 ? N1 Fe1 N3 91.79(17) . 3_666 ? N2 Fe1 N3 93.53(16) . 3_666 ? N2 Fe1 N3 86.47(16) 3_666 3_666 ? N1 Fe1 N3 91.79(17) 3_666 . ? N1 Fe1 N3 88.21(17) . . ? N2 Fe1 N3 86.47(16) . . ? N2 Fe1 N3 93.53(16) 3_666 . ? N3 Fe1 N3 180.000(1) 3_666 . ? C13 O1 C15 115.5(4) . . ? C14 O2 C21 122.0(4) . . ? C1 N1 Fe1 175.3(4) . . ? C2 N2 C6 117.3(4) . . ? C2 N2 Fe1 120.0(3) . . ? C6 N2 Fe1 122.6(3) . . ? C11 N3 C7 116.3(4) . . ? C11 N3 Fe1 122.6(3) . . ? C7 N3 Fe1 120.9(3) . . ? C12 N4 C6 121.7(4) . . ? C12 N4 C11 121.7(4) . . ? C6 N4 C11 116.7(4) . . ? C13 N5 C12 112.4(4) . . ? C13 N6 C14 112.5(4) . . ? C14 N7 C12 113.1(4) . . ? N1 C1 Se1 178.0(5) . . ? N2 C2 C3 123.2(5) . . ? N2 C2 H2A 118.4 . . ? C3 C2 H2A 118.4 . . ? C2 C3 C4 119.6(5) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C3 C4 C5 118.1(5) . . ? C3 C4 H4A 121.0 . . ? C5 C4 H4A 121.0 . . ? C6 C5 C4 119.1(5) . . ? C6 C5 H5A 120.4 . . ? C4 C5 H5A 120.4 . . ? N2 C6 C5 122.6(5) . . ? N2 C6 N4 116.5(4) . . ? C5 C6 N4 120.8(4) . . ? N3 C7 C8 123.2(5) . . ? N3 C7 H7A 118.4 . . ? C8 C7 H7A 118.4 . . ? C7 C8 C9 119.5(5) . . ? C7 C8 H8A 120.2 . . ? C9 C8 H8A 120.2 . . ? C10 C9 C8 118.0(5) . . ? C10 C9 H9A 121.0 . . ? C8 C9 H9A 121.0 . . ? C9 C10 C11 119.1(5) . . ? C9 C10 H10A 120.4 . . ? C11 C10 H10A 120.4 . . ? N3 C11 C10 123.7(4) . . ? N3 C11 N4 116.0(4) . . ? C10 C11 N4 120.3(4) . . ? N7 C12 N5 126.1(4) . . ? N7 C12 N4 117.1(4) . . ? N5 C12 N4 116.7(4) . . ? N6 C13 N5 128.2(5) . . ? N6 C13 O1 119.0(4) . . ? N5 C13 O1 112.8(4) . . ? N7 C14 N6 127.5(5) . . ? N7 C14 O2 120.5(4) . . ? N6 C14 O2 111.9(4) . . ? C16 C15 C20 122.0(5) . . ? C16 C15 O1 118.8(5) . . ? C20 C15 O1 119.1(5) . . ? C15 C16 C17 118.9(6) . . ? C15 C16 H16A 120.6 . . ? C17 C16 H16A 120.6 . . ? C18 C17 C16 120.3(6) . . ? C18 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? C19 C18 C17 119.6(6) . . ? C19 C18 H18A 120.2 . . ? C17 C18 H18A 120.2 . . ? C18 C19 C20 120.5(6) . . ? C18 C19 H19A 119.7 . . ? C20 C19 H19A 119.7 . . ? C15 C20 C19 118.6(6) . . ? C15 C20 H20A 120.7 . . ? C19 C20 H20A 120.7 . . ? C26 C21 C22 122.2(5) . . ? C26 C21 O2 121.2(5) . . ? C22 C21 O2 116.4(5) . . ? C21 C22 C23 118.3(5) . . ? C21 C22 H22A 120.9 . . ? C23 C22 H22A 120.9 . . ? C24 C23 C22 120.8(5) . . ? C24 C23 H23A 119.6 . . ? C22 C23 H23A 119.6 . . ? C23 C24 C25 119.8(5) . . ? C23 C24 H24A 120.1 . . ? C25 C24 H24A 120.1 . . ? C26 C25 C24 120.7(6) . . ? C26 C25 H25A 119.6 . . ? C24 C25 H25A 119.6 . . ? C25 C26 C21 118.2(5) . . ? C25 C26 H26A 120.9 . . ? C21 C26 H26A 120.9 . . ? Cl2 C1S Cl1 113.3(7) . . ? Cl2 C1S H1SA 108.9 . . ? Cl1 C1S H1SA 108.9 . . ? Cl2 C1S H1SB 108.9 . . ? Cl1 C1S H1SB 108.9 . . ? H1SA C1S H1SB 107.7 . . ? Cl3 C2S Cl4 110.6(11) . . ? Cl3 C2S H2SA 109.5 . . ? Cl4 C2S H2SA 109.5 . . ? Cl3 C2S H2SB 109.5 . . ? Cl4 C2S H2SB 109.5 . . ? H2SA C2S H2SB 108.1 . . ? Cl6 C3S Cl5 111.4(9) . . ? Cl6 C3S H3SA 109.4 . . ? Cl5 C3S H3SA 109.4 . . ? Cl6 C3S H3SB 109.4 . . ? Cl5 C3S H3SB 109.4 . . ? H3SA C3S H3SB 108.0 . . ? Cl8 C4S Cl7 112.1(12) . . ? Cl8 C4S H4SA 109.2 . . ? Cl7 C4S H4SA 109.2 . . ? Cl8 C4S H4SB 109.2 . . ? Cl7 C4S H4SB 109.2 . . ? H4SA C4S H4SB 107.9 . . ? C5S O1S H1S 118(7) . . ? O1S C5S H9 109.5 . . ? O1S C5S H10 109.5 . . ? H9 C5S H10 109.5 . . ? O1S C5S H11 109.5 . . ? H9 C5S H11 109.5 . . ? H10 C5S H11 109.5 . . ? C6S O2S H2S 137(6) . . ? O2S C6S H12 109.5 . . ? O2S C6S H13 109.5 . . ? H12 C6S H13 109.5 . . ? O2S C6S H14 109.5 . . ? H12 C6S H14 109.5 . . ? H13 C6S H14 109.5 . . ? 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 O1S H1S O2S 0.97(2) 1.95(6) 2.828(11) 150(10) . O2S H2S N5 0.98(2) 2.16(5) 3.074(8) 155(9) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.837 _refine_diff_density_min -0.945 _refine_diff_density_rms 0.131 data_9acn4a100 _database_code_depnum_ccdc_archive 'CCDC 921065' #TrackingRef '17081_web_deposit_cif_file_4_OlivierRoubeau_1358848554.Cpd3-9acn4a100.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H16 F20 Fe N14 O4 S2, 2(C2 H3 N)' _chemical_formula_sum 'C56 H22 F20 Fe N16 O4 S2' _chemical_formula_weight 1482.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0020 0.0020 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' H H 0.0000 0.0000 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' N N -0.0031 0.0040 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' O O -0.0041 0.0074 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' F F -0.0053 0.0125 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' S S 0.1206 0.1480 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Fe Fe 0.2064 0.9930 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3499(8) _cell_length_b 11.3580(10) _cell_length_c 15.689(2) _cell_angle_alpha 92.9740(10) _cell_angle_beta 102.6160(10) _cell_angle_gamma 99.2570(10) _cell_volume 1427.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9974 _cell_measurement_theta_min 3.68 _cell_measurement_theta_max 33.61 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 0.586 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details 'SADABS Bruker AXS Madison WI US' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20057 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0622 _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 -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 33.62 _reflns_number_total 8387 _reflns_number_gt 7212 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.68a' _computing_data_reduction 'Bruker SAINT v7.68a' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogens were refined anisotropically. Hydrogens were placed geometrically on their carrier atom and refined with a riding model. ; _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^)+(0.0656P)^2^+0.4321P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8387 _refine_ls_number_parameters 449 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1264 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.5000 0.5000 0.5000 0.01262(8) Uani 1 2 d S . . S1 S 0.42689(5) 0.70754(4) 0.75438(2) 0.02355(10) Uani 1 1 d . . . F1 F 0.51026(14) 0.70908(10) 0.95714(6) 0.0303(2) Uani 1 1 d . . . F2 F 0.51762(17) 0.80765(11) 1.11790(7) 0.0394(3) Uani 1 1 d . . . F3 F 0.69553(16) 0.72750(10) 1.26274(6) 0.0348(3) Uani 1 1 d . . . F4 F 0.87345(13) 0.55241(10) 1.24531(7) 0.0311(2) Uani 1 1 d . . . F5 F 0.87059(14) 0.45421(10) 1.08318(7) 0.0316(2) Uani 1 1 d . . . F6 F 1.31214(12) 0.90311(9) 0.86758(6) 0.0257(2) Uani 1 1 d . . . F7 F 1.43649(13) 1.01256(10) 0.74009(7) 0.0305(2) Uani 1 1 d . . . F8 F 1.22485(15) 1.06923(11) 0.59657(7) 0.0349(3) Uani 1 1 d . . . F9 F 0.89105(14) 1.01489(10) 0.57943(7) 0.0328(2) Uani 1 1 d . . . F10 F 0.76684(12) 0.90622(9) 0.70672(7) 0.0266(2) Uani 1 1 d . . . O1 O 0.67979(15) 0.52036(10) 0.93624(7) 0.0214(2) Uani 1 1 d . . . O2 O 0.97663(14) 0.85003(9) 0.85553(7) 0.0201(2) Uani 1 1 d . . . N1 N 0.47413(15) 0.58295(11) 0.60588(8) 0.0169(2) Uani 1 1 d . . . N2 N 0.73636(15) 0.57802(10) 0.52032(8) 0.0148(2) Uani 1 1 d . . . N3 N 0.58474(15) 0.36951(10) 0.56616(8) 0.0154(2) Uani 1 1 d . . . N4 N 0.78437(14) 0.51340(10) 0.66292(7) 0.0141(2) Uani 1 1 d . . . N5 N 0.73126(15) 0.51235(10) 0.80238(8) 0.0162(2) Uani 1 1 d . . . N6 N 0.88363(15) 0.68415(10) 0.75736(8) 0.0159(2) Uani 1 1 d . . . N7 N 0.83168(15) 0.69023(11) 0.90061(8) 0.0174(2) Uani 1 1 d . . . C1 C 0.45352(17) 0.63522(13) 0.66740(9) 0.0169(2) Uani 1 1 d . . . C2 C 0.79479(18) 0.63048(13) 0.45514(9) 0.0176(3) Uani 1 1 d . . . H2A H 0.7195 0.6300 0.4001 0.021 Uiso 1 1 calc R . . C3 C 0.95881(18) 0.68479(13) 0.46477(10) 0.0194(3) Uani 1 1 d . . . H3A H 0.9942 0.7233 0.4180 0.023 Uiso 1 1 calc R . . C4 C 1.07114(18) 0.68212(13) 0.54412(10) 0.0197(3) Uani 1 1 d . . . H4A H 1.1846 0.7190 0.5526 0.024 Uiso 1 1 calc R . . C5 C 1.01479(17) 0.62475(13) 0.61066(9) 0.0172(3) Uani 1 1 d . . . H5A H 1.0896 0.6195 0.6649 0.021 Uiso 1 1 calc R . . C6 C 0.84717(17) 0.57523(11) 0.59649(9) 0.0147(2) Uani 1 1 d . . . C7 C 0.52220(18) 0.25333(13) 0.53752(10) 0.0186(3) Uani 1 1 d . . . H7A H 0.4426 0.2352 0.4831 0.022 Uiso 1 1 calc R . . C8 C 0.5697(2) 0.16014(13) 0.58428(11) 0.0215(3) Uani 1 1 d . . . H8A H 0.5243 0.0795 0.5619 0.026 Uiso 1 1 calc R . . C9 C 0.68452(19) 0.18562(13) 0.66436(10) 0.0210(3) Uani 1 1 d . . . H9A H 0.7143 0.1230 0.6990 0.025 Uiso 1 1 calc R . . C10 C 0.75458(18) 0.30340(12) 0.69272(10) 0.0179(3) Uani 1 1 d . . . H10A H 0.8359 0.3233 0.7464 0.022 Uiso 1 1 calc R . . C11 C 0.70343(17) 0.39237(12) 0.64093(9) 0.0152(2) Uani 1 1 d . . . C12 C 0.80061(16) 0.57111(12) 0.74409(9) 0.0143(2) Uani 1 1 d . . . C13 C 0.75158(17) 0.57892(12) 0.87709(9) 0.0167(2) Uani 1 1 d . . . C14 C 0.89313(17) 0.73507(12) 0.83563(9) 0.0164(2) Uani 1 1 d . . . C15 C 0.69195(19) 0.58063(13) 1.01696(9) 0.0190(3) Uani 1 1 d . . . C16 C 0.6023(2) 0.67092(14) 1.02685(10) 0.0214(3) Uani 1 1 d . . . C17 C 0.6041(2) 0.72075(14) 1.10921(10) 0.0240(3) Uani 1 1 d . . . C18 C 0.6940(2) 0.67934(14) 1.18276(10) 0.0240(3) Uani 1 1 d . . . C19 C 0.7832(2) 0.58973(14) 1.17373(10) 0.0224(3) Uani 1 1 d . . . C20 C 0.78231(19) 0.54063(13) 1.09123(10) 0.0209(3) Uani 1 1 d . . . C21 C 1.03755(19) 0.90200(12) 0.78858(10) 0.0196(3) Uani 1 1 d . . . C22 C 1.2078(2) 0.92942(13) 0.79674(10) 0.0211(3) Uani 1 1 d . . . C23 C 1.2717(2) 0.98563(14) 0.73205(11) 0.0235(3) Uani 1 1 d . . . C24 C 1.1646(2) 1.01386(14) 0.65905(11) 0.0255(3) Uani 1 1 d . . . C25 C 0.9947(2) 0.98675(14) 0.65030(11) 0.0240(3) Uani 1 1 d . . . C26 C 0.93151(19) 0.93143(13) 0.71501(10) 0.0212(3) Uani 1 1 d . . . N1S N 0.9401(3) 0.15236(18) 0.86506(13) 0.0470(4) Uani 1 1 d . . . C1S C 0.8551(3) 0.08867(19) 0.89711(13) 0.0373(4) Uani 1 1 d . . . C2S C 0.7459(3) 0.0062(2) 0.93641(14) 0.0439(5) Uani 1 1 d . . . H2S1 H 0.6670 -0.0487 0.8902 0.066 Uiso 1 1 calc R . . H2S2 H 0.6843 0.0516 0.9688 0.066 Uiso 1 1 calc R . . H2S3 H 0.8129 -0.0399 0.9767 0.066 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 0.01362(13) 0.01281(13) 0.01169(13) 0.00038(9) 0.00458(9) 0.00101(9) S1 0.02154(18) 0.0309(2) 0.01806(17) -0.00731(13) 0.00437(13) 0.00747(14) F1 0.0411(6) 0.0356(5) 0.0169(4) 0.0068(4) 0.0042(4) 0.0169(5) F2 0.0624(8) 0.0363(6) 0.0274(5) 0.0020(4) 0.0132(5) 0.0283(6) F3 0.0605(7) 0.0282(5) 0.0152(4) -0.0009(4) 0.0098(5) 0.0056(5) F4 0.0335(5) 0.0336(5) 0.0219(5) 0.0093(4) -0.0028(4) 0.0035(4) F5 0.0320(5) 0.0322(5) 0.0358(6) 0.0075(4) 0.0112(4) 0.0150(4) F6 0.0253(5) 0.0295(5) 0.0216(4) 0.0011(4) 0.0062(4) 0.0021(4) F7 0.0242(5) 0.0331(5) 0.0351(6) 0.0027(4) 0.0151(4) -0.0032(4) F8 0.0403(6) 0.0372(6) 0.0309(5) 0.0127(4) 0.0195(5) -0.0004(5) F9 0.0365(6) 0.0357(6) 0.0278(5) 0.0127(4) 0.0076(4) 0.0079(4) F10 0.0220(4) 0.0236(5) 0.0356(5) 0.0059(4) 0.0099(4) 0.0023(4) O1 0.0294(6) 0.0187(5) 0.0175(5) 0.0014(4) 0.0127(4) -0.0014(4) O2 0.0259(5) 0.0153(5) 0.0191(5) -0.0005(4) 0.0108(4) -0.0028(4) N1 0.0170(5) 0.0179(5) 0.0159(5) 0.0011(4) 0.0047(4) 0.0026(4) N2 0.0161(5) 0.0148(5) 0.0139(5) 0.0018(4) 0.0048(4) 0.0016(4) N3 0.0160(5) 0.0143(5) 0.0163(5) 0.0007(4) 0.0061(4) 0.0011(4) N4 0.0159(5) 0.0136(5) 0.0131(5) 0.0020(4) 0.0054(4) 0.0003(4) N5 0.0181(5) 0.0154(5) 0.0159(5) 0.0024(4) 0.0066(4) 0.0011(4) N6 0.0174(5) 0.0150(5) 0.0160(5) 0.0014(4) 0.0062(4) 0.0016(4) N7 0.0193(5) 0.0172(5) 0.0162(5) 0.0021(4) 0.0066(4) 0.0008(4) C1 0.0149(6) 0.0188(6) 0.0166(6) 0.0006(5) 0.0030(5) 0.0026(5) C2 0.0180(6) 0.0192(6) 0.0167(6) 0.0039(5) 0.0064(5) 0.0022(5) C3 0.0196(6) 0.0206(6) 0.0202(6) 0.0050(5) 0.0099(5) 0.0012(5) C4 0.0167(6) 0.0207(6) 0.0222(7) 0.0033(5) 0.0076(5) 0.0002(5) C5 0.0153(6) 0.0195(6) 0.0173(6) 0.0027(5) 0.0049(5) 0.0026(5) C6 0.0160(6) 0.0129(5) 0.0158(6) 0.0019(4) 0.0063(5) 0.0007(4) C7 0.0194(6) 0.0160(6) 0.0207(6) -0.0005(5) 0.0073(5) 0.0006(5) C8 0.0241(7) 0.0139(6) 0.0274(7) 0.0007(5) 0.0099(6) 0.0007(5) C9 0.0236(7) 0.0166(6) 0.0248(7) 0.0051(5) 0.0097(6) 0.0034(5) C10 0.0193(6) 0.0162(6) 0.0202(6) 0.0041(5) 0.0078(5) 0.0037(5) C11 0.0164(6) 0.0142(5) 0.0161(6) 0.0020(4) 0.0065(5) 0.0016(5) C12 0.0142(5) 0.0145(6) 0.0148(6) 0.0025(4) 0.0043(4) 0.0027(4) C13 0.0181(6) 0.0164(6) 0.0171(6) 0.0033(5) 0.0074(5) 0.0020(5) C14 0.0164(6) 0.0139(6) 0.0188(6) 0.0013(5) 0.0054(5) 0.0006(5) C15 0.0228(7) 0.0189(6) 0.0162(6) 0.0020(5) 0.0090(5) -0.0003(5) C16 0.0271(7) 0.0223(7) 0.0157(6) 0.0051(5) 0.0054(5) 0.0048(6) C17 0.0333(8) 0.0220(7) 0.0198(7) 0.0026(5) 0.0097(6) 0.0090(6) C18 0.0360(8) 0.0207(7) 0.0144(6) 0.0010(5) 0.0076(6) 0.0002(6) C19 0.0227(7) 0.0233(7) 0.0185(7) 0.0061(5) 0.0016(5) -0.0010(5) C20 0.0205(7) 0.0197(6) 0.0242(7) 0.0055(5) 0.0076(5) 0.0035(5) C21 0.0252(7) 0.0136(6) 0.0210(6) 0.0004(5) 0.0111(6) -0.0009(5) C22 0.0235(7) 0.0179(6) 0.0215(7) -0.0006(5) 0.0078(5) 0.0000(5) C23 0.0227(7) 0.0207(7) 0.0277(7) 0.0001(5) 0.0125(6) -0.0026(5) C24 0.0323(8) 0.0216(7) 0.0258(7) 0.0044(6) 0.0158(6) 0.0004(6) C25 0.0291(8) 0.0205(7) 0.0237(7) 0.0048(5) 0.0087(6) 0.0033(6) C26 0.0229(7) 0.0169(6) 0.0255(7) 0.0027(5) 0.0099(6) 0.0020(5) N1S 0.0568(12) 0.0395(10) 0.0425(10) -0.0008(8) 0.0076(9) 0.0092(9) C1S 0.0454(11) 0.0408(10) 0.0270(9) -0.0030(7) 0.0037(8) 0.0197(9) C2S 0.0441(11) 0.0622(14) 0.0343(10) 0.0081(9) 0.0158(9) 0.0247(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 N1 1.9374(13) 2_666 ? Fe1 N1 1.9374(13) . ? Fe1 N2 1.9786(12) 2_666 ? Fe1 N2 1.9786(12) . ? Fe1 N3 1.9877(12) . ? Fe1 N3 1.9877(12) 2_666 ? S1 C1 1.6313(15) . ? F1 C16 1.3281(17) . ? F2 C17 1.3315(18) . ? F3 C18 1.3392(18) . ? F4 C19 1.3385(17) . ? F5 C20 1.3354(18) . ? F6 C22 1.3335(18) . ? F7 C23 1.3369(18) . ? F8 C24 1.3367(18) . ? F9 C25 1.3391(19) . ? F10 C26 1.3345(18) . ? O1 C13 1.3570(16) . ? O1 C15 1.3836(17) . ? O2 C14 1.3632(17) . ? O2 C21 1.3826(17) . ? N1 C1 1.1661(19) . ? N2 C6 1.3474(17) . ? N2 C2 1.3515(17) . ? N3 C11 1.3429(18) . ? N3 C7 1.3529(18) . ? N4 C12 1.3707(17) . ? N4 C11 1.4197(17) . ? N4 C6 1.4320(16) . ? N5 C13 1.3245(18) . ? N5 C12 1.3369(17) . ? N6 C14 1.3106(18) . ? N6 C12 1.3399(17) . ? N7 C13 1.3242(18) . ? N7 C14 1.3268(18) . ? C2 C3 1.381(2) . ? C2 H2A 0.9500 . ? C3 C4 1.390(2) . ? C3 H3A 0.9500 . ? C4 C5 1.3865(19) . ? C4 H4A 0.9500 . ? C5 C6 1.3866(19) . ? C5 H5A 0.9500 . ? C7 C8 1.380(2) . ? C7 H7A 0.9500 . ? C8 C9 1.389(2) . ? C8 H8A 0.9500 . ? C9 C10 1.379(2) . ? C9 H9A 0.9500 . ? C10 C11 1.3915(18) . ? C10 H10A 0.9500 . ? C15 C20 1.384(2) . ? C15 C16 1.385(2) . ? C16 C17 1.380(2) . ? C17 C18 1.381(2) . ? C18 C19 1.373(2) . ? C19 C20 1.381(2) . ? C21 C22 1.382(2) . ? C21 C26 1.384(2) . ? C22 C23 1.384(2) . ? C23 C24 1.377(2) . ? C24 C25 1.377(2) . ? C25 C26 1.378(2) . ? N1S C1S 1.144(3) . ? C1S C2S 1.456(3) . ? C2S H2S1 0.9800 . ? C2S H2S2 0.9800 . ? C2S H2S3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 179.999(1) 2_666 . ? N1 Fe1 N2 91.84(5) 2_666 2_666 ? N1 Fe1 N2 88.16(5) . 2_666 ? N1 Fe1 N2 88.16(5) 2_666 . ? N1 Fe1 N2 91.84(5) . . ? N2 Fe1 N2 180.0 2_666 . ? N1 Fe1 N3 88.30(5) 2_666 . ? N1 Fe1 N3 91.70(5) . . ? N2 Fe1 N3 93.85(5) 2_666 . ? N2 Fe1 N3 86.15(5) . . ? N1 Fe1 N3 91.70(5) 2_666 2_666 ? N1 Fe1 N3 88.30(5) . 2_666 ? N2 Fe1 N3 86.15(5) 2_666 2_666 ? N2 Fe1 N3 93.85(5) . 2_666 ? N3 Fe1 N3 180.0 . 2_666 ? C13 O1 C15 118.36(11) . . ? C14 O2 C21 115.50(11) . . ? C1 N1 Fe1 177.10(12) . . ? C6 N2 C2 117.29(12) . . ? C6 N2 Fe1 122.26(9) . . ? C2 N2 Fe1 120.32(9) . . ? C11 N3 C7 117.46(12) . . ? C11 N3 Fe1 121.91(9) . . ? C7 N3 Fe1 120.62(10) . . ? C12 N4 C11 121.96(11) . . ? C12 N4 C6 120.37(11) . . ? C11 N4 C6 117.66(11) . . ? C13 N5 C12 112.47(12) . . ? C14 N6 C12 113.30(12) . . ? C13 N7 C14 110.54(12) . . ? N1 C1 S1 179.16(14) . . ? N2 C2 C3 123.10(13) . . ? N2 C2 H2A 118.4 . . ? C3 C2 H2A 118.4 . . ? C2 C3 C4 118.78(13) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C5 C4 C3 118.91(13) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C4 C5 C6 118.69(13) . . ? C4 C5 H5A 120.7 . . ? C6 C5 H5A 120.7 . . ? N2 C6 C5 123.15(12) . . ? N2 C6 N4 116.33(12) . . ? C5 C6 N4 120.48(12) . . ? N3 C7 C8 122.52(14) . . ? N3 C7 H7A 118.7 . . ? C8 C7 H7A 118.7 . . ? C7 C8 C9 119.23(13) . . ? C7 C8 H8A 120.4 . . ? C9 C8 H8A 120.4 . . ? C10 C9 C8 118.91(13) . . ? C10 C9 H9A 120.5 . . ? C8 C9 H9A 120.5 . . ? C9 C10 C11 118.50(14) . . ? C9 C10 H10A 120.8 . . ? C11 C10 H10A 120.8 . . ? N3 C11 C10 123.17(13) . . ? N3 C11 N4 116.41(11) . . ? C10 C11 N4 120.30(13) . . ? N5 C12 N6 125.48(13) . . ? N5 C12 N4 118.38(12) . . ? N6 C12 N4 116.12(12) . . ? N7 C13 N5 129.25(13) . . ? N7 C13 O1 117.91(12) . . ? N5 C13 O1 112.83(12) . . ? N6 C14 N7 128.94(13) . . ? N6 C14 O2 117.58(12) . . ? N7 C14 O2 113.48(12) . . ? C20 C15 O1 118.71(14) . . ? C20 C15 C16 118.79(14) . . ? O1 C15 C16 122.13(13) . . ? F1 C16 C17 118.96(14) . . ? F1 C16 C15 120.42(14) . . ? C17 C16 C15 120.61(14) . . ? F2 C17 C16 120.08(14) . . ? F2 C17 C18 119.98(14) . . ? C16 C17 C18 119.94(15) . . ? F3 C18 C19 120.08(14) . . ? F3 C18 C17 119.97(15) . . ? C19 C18 C17 119.94(14) . . ? F4 C19 C18 119.49(14) . . ? F4 C19 C20 120.45(15) . . ? C18 C19 C20 120.04(14) . . ? F5 C20 C19 119.54(14) . . ? F5 C20 C15 119.77(14) . . ? C19 C20 C15 120.68(14) . . ? C22 C21 O2 119.38(14) . . ? C22 C21 C26 119.27(14) . . ? O2 C21 C26 121.31(14) . . ? F6 C22 C21 120.20(13) . . ? F6 C22 C23 119.44(14) . . ? C21 C22 C23 120.36(15) . . ? F7 C23 C24 119.94(14) . . ? F7 C23 C22 120.37(15) . . ? C24 C23 C22 119.70(15) . . ? F8 C24 C25 119.41(16) . . ? F8 C24 C23 120.24(15) . . ? C25 C24 C23 120.34(14) . . ? F9 C25 C24 120.16(14) . . ? F9 C25 C26 119.99(15) . . ? C24 C25 C26 119.85(15) . . ? F10 C26 C25 119.72(14) . . ? F10 C26 C21 119.80(13) . . ? C25 C26 C21 120.48(15) . . ? N1S C1S C2S 178.9(2) . . ? C1S C2S H2S1 109.5 . . ? C1S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? C1S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.496 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.076 data_9acn4a190 _database_code_depnum_ccdc_archive 'CCDC 921066' #TrackingRef '17082_web_deposit_cif_file_5_OlivierRoubeau_1358848554.Cpd3-9acn4a190.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H16 F20 Fe N14 O4 S2, 2(C2 H3 N)' _chemical_formula_sum 'C56 H22 F20 Fe N16 O4 S2' _chemical_formula_weight 1482.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0020 0.0020 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' H H 0.0000 0.0000 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' N N -0.0031 0.0040 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' O O -0.0041 0.0074 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' F F -0.0053 0.0125 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' S S 0.1206 0.1480 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Fe Fe 0.2064 0.9930 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4120(7) _cell_length_b 11.4159(9) _cell_length_c 15.757(2) _cell_angle_alpha 93.2930(10) _cell_angle_beta 102.2240(10) _cell_angle_gamma 99.4470(10) _cell_volume 1452.1(2) _cell_formula_units_Z 1 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 9542 _cell_measurement_theta_min 3.61 _cell_measurement_theta_max 33.58 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.696 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 0.576 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details 'SADABS Bruker AXS Madison WI US' _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20212 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0742 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 33.62 _reflns_number_total 8576 _reflns_number_gt 6978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.68a' _computing_data_reduction 'Bruker SAINT v7.68a' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogens were refined anisotropically. Hydrogens were placed geometrically on their carrier atom and refined with a riding model. ; _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^)+(0.1110P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8576 _refine_ls_number_parameters 449 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.1556 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.5000 0.5000 0.5000 0.02103(10) Uani 1 2 d S . . S1 S 0.42228(6) 0.70457(5) 0.75367(3) 0.04177(14) Uani 1 1 d . . . F1 F 0.51093(19) 0.70475(13) 0.95904(8) 0.0524(3) Uani 1 1 d . . . F2 F 0.5245(3) 0.80219(16) 1.12051(10) 0.0728(5) Uani 1 1 d . . . F3 F 0.7064(2) 0.72358(14) 1.26139(8) 0.0653(5) Uani 1 1 d . . . F4 F 0.88291(19) 0.55123(14) 1.23968(9) 0.0577(4) Uani 1 1 d . . . F5 F 0.87409(19) 0.45420(14) 1.07708(10) 0.0567(4) Uani 1 1 d . . . F6 F 1.30225(16) 0.90206(12) 0.86513(8) 0.0464(3) Uani 1 1 d . . . F7 F 1.42810(18) 1.01212(14) 0.73971(10) 0.0569(4) Uani 1 1 d . . . F8 F 1.2214(2) 1.06954(15) 0.59771(10) 0.0657(4) Uani 1 1 d . . . F9 F 0.8905(2) 1.01401(15) 0.57925(10) 0.0609(4) Uani 1 1 d . . . F10 F 0.76468(16) 0.90423(12) 0.70422(9) 0.0481(3) Uani 1 1 d . . . O1 O 0.67924(18) 0.51926(12) 0.93382(8) 0.0366(3) Uani 1 1 d . . . O2 O 0.96929(18) 0.84820(11) 0.85245(8) 0.0344(3) Uani 1 1 d . . . N1 N 0.47413(17) 0.58229(13) 0.60627(9) 0.0273(3) Uani 1 1 d . . . N2 N 0.73572(17) 0.57725(12) 0.52003(8) 0.0235(3) Uani 1 1 d . . . N3 N 0.58210(17) 0.36931(12) 0.56462(9) 0.0252(3) Uani 1 1 d . . . N4 N 0.78153(16) 0.51186(11) 0.66133(8) 0.0227(2) Uani 1 1 d . . . N5 N 0.72914(18) 0.51153(12) 0.80023(9) 0.0270(3) Uani 1 1 d . . . N6 N 0.87842(17) 0.68210(12) 0.75495(9) 0.0260(3) Uani 1 1 d . . . N7 N 0.82772(18) 0.68876(13) 0.89763(9) 0.0287(3) Uani 1 1 d . . . C1 C 0.4513(2) 0.63339(15) 0.66715(11) 0.0274(3) Uani 1 1 d . . . C2 C 0.7950(2) 0.62987(15) 0.45568(11) 0.0289(3) Uani 1 1 d . . . H2A H 0.7208 0.6306 0.4012 0.035 Uiso 1 1 calc R . . C3 C 0.9578(2) 0.68244(16) 0.46545(12) 0.0317(3) Uani 1 1 d . . . H3A H 0.9939 0.7209 0.4192 0.038 Uiso 1 1 calc R . . C4 C 1.0686(2) 0.67859(16) 0.54360(12) 0.0319(3) Uani 1 1 d . . . H4A H 1.1816 0.7146 0.5519 0.038 Uiso 1 1 calc R . . C5 C 1.0116(2) 0.62123(15) 0.60939(11) 0.0276(3) Uani 1 1 d . . . H5A H 1.0852 0.6150 0.6630 0.033 Uiso 1 1 calc R . . C6 C 0.84451(19) 0.57311(13) 0.59513(10) 0.0237(3) Uani 1 1 d . . . C7 C 0.5186(2) 0.25364(15) 0.53556(12) 0.0302(3) Uani 1 1 d . . . H7A H 0.4401 0.2360 0.4814 0.036 Uiso 1 1 calc R . . C8 C 0.5633(3) 0.16061(15) 0.58155(13) 0.0360(4) Uani 1 1 d . . . H8A H 0.5165 0.0804 0.5593 0.043 Uiso 1 1 calc R . . C9 C 0.6772(3) 0.18546(16) 0.66041(13) 0.0354(4) Uani 1 1 d . . . H9A H 0.7059 0.1227 0.6943 0.042 Uiso 1 1 calc R . . C10 C 0.7487(2) 0.30230(15) 0.68927(12) 0.0300(3) Uani 1 1 d . . . H10A H 0.8295 0.3216 0.7425 0.036 Uiso 1 1 calc R . . C11 C 0.69963(19) 0.39121(13) 0.63858(10) 0.0244(3) Uani 1 1 d . . . C12 C 0.79708(19) 0.56931(13) 0.74202(10) 0.0232(3) Uani 1 1 d . . . C13 C 0.7497(2) 0.57796(15) 0.87446(11) 0.0276(3) Uani 1 1 d . . . C14 C 0.8877(2) 0.73361(14) 0.83274(11) 0.0270(3) Uani 1 1 d . . . C15 C 0.6939(2) 0.57893(16) 1.01472(11) 0.0312(3) Uani 1 1 d . . . C16 C 0.6047(3) 0.66721(17) 1.02709(12) 0.0355(4) Uani 1 1 d . . . C17 C 0.6098(3) 0.71620(18) 1.10938(13) 0.0416(4) Uani 1 1 d . . . C18 C 0.7016(3) 0.67545(18) 1.18114(12) 0.0421(5) Uani 1 1 d . . . C19 C 0.7901(3) 0.58750(19) 1.16991(12) 0.0399(4) Uani 1 1 d . . . C20 C 0.7864(2) 0.53977(17) 1.08715(13) 0.0361(4) Uani 1 1 d . . . C21 C 1.0315(2) 0.90001(15) 0.78597(12) 0.0332(4) Uani 1 1 d . . . C22 C 1.1999(3) 0.92814(16) 0.79466(12) 0.0362(4) Uani 1 1 d . . . C23 C 1.2649(3) 0.98516(18) 0.73107(14) 0.0417(4) Uani 1 1 d . . . C24 C 1.1600(3) 1.01285(19) 0.65880(15) 0.0460(5) Uani 1 1 d . . . C25 C 0.9920(3) 0.98538(18) 0.64968(14) 0.0438(5) Uani 1 1 d . . . C26 C 0.9280(3) 0.92928(16) 0.71314(14) 0.0368(4) Uani 1 1 d . . . N1S N 0.9392(5) 0.1541(3) 0.8604(2) 0.0892(9) Uani 1 1 d . . . C1S C 0.8543(5) 0.0938(3) 0.8948(2) 0.0700(8) Uani 1 1 d . . . C2S C 0.7468(5) 0.0146(4) 0.9366(2) 0.0918(12) Uani 1 1 d . . . H2S1 H 0.6646 -0.0397 0.8919 0.138 Uiso 1 1 calc R . . H2S2 H 0.6904 0.0620 0.9703 0.138 Uiso 1 1 calc R . . H2S3 H 0.8132 -0.0319 0.9756 0.138 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 0.02097(16) 0.02280(16) 0.01916(16) 0.00010(10) 0.00668(11) 0.00128(11) S1 0.0360(3) 0.0587(3) 0.0300(2) -0.0140(2) 0.00627(19) 0.0146(2) F1 0.0689(9) 0.0628(8) 0.0300(6) 0.0120(6) 0.0064(6) 0.0282(7) F2 0.1173(15) 0.0680(10) 0.0482(8) 0.0025(7) 0.0241(9) 0.0539(10) F3 0.1127(14) 0.0543(8) 0.0255(6) -0.0013(5) 0.0148(7) 0.0078(8) F4 0.0575(9) 0.0663(9) 0.0403(7) 0.0199(6) -0.0076(6) 0.0040(7) F5 0.0549(8) 0.0617(8) 0.0635(9) 0.0160(7) 0.0201(7) 0.0273(7) F6 0.0455(7) 0.0533(7) 0.0385(6) -0.0007(5) 0.0116(5) 0.0022(6) F7 0.0451(7) 0.0618(9) 0.0650(9) 0.0036(7) 0.0292(7) -0.0083(6) F8 0.0776(11) 0.0678(10) 0.0601(9) 0.0237(8) 0.0402(8) -0.0007(8) F9 0.0706(10) 0.0674(9) 0.0503(8) 0.0250(7) 0.0172(7) 0.0169(8) F10 0.0410(7) 0.0440(7) 0.0616(8) 0.0114(6) 0.0173(6) 0.0047(5) O1 0.0509(8) 0.0320(6) 0.0286(6) 0.0026(5) 0.0213(6) -0.0033(6) O2 0.0444(7) 0.0264(6) 0.0318(6) -0.0027(5) 0.0189(6) -0.0066(5) N1 0.0263(6) 0.0306(6) 0.0252(6) 0.0008(5) 0.0072(5) 0.0041(5) N2 0.0246(6) 0.0249(6) 0.0214(6) 0.0023(4) 0.0076(5) 0.0026(5) N3 0.0246(6) 0.0236(6) 0.0272(6) 0.0009(5) 0.0090(5) 0.0002(5) N4 0.0247(6) 0.0218(6) 0.0214(6) 0.0029(4) 0.0075(5) 0.0005(5) N5 0.0296(7) 0.0263(6) 0.0265(6) 0.0045(5) 0.0114(5) 0.0020(5) N6 0.0280(7) 0.0246(6) 0.0264(6) 0.0028(5) 0.0105(5) 0.0013(5) N7 0.0307(7) 0.0299(7) 0.0255(6) 0.0032(5) 0.0098(5) 0.0007(5) C1 0.0242(7) 0.0329(7) 0.0249(7) -0.0007(6) 0.0052(6) 0.0063(6) C2 0.0292(8) 0.0336(8) 0.0257(7) 0.0072(6) 0.0102(6) 0.0037(6) C3 0.0308(8) 0.0366(8) 0.0307(8) 0.0091(6) 0.0150(7) 0.0017(7) C4 0.0244(7) 0.0364(8) 0.0359(9) 0.0065(7) 0.0117(6) 0.0010(6) C5 0.0228(7) 0.0314(7) 0.0279(7) 0.0043(6) 0.0058(6) 0.0028(6) C6 0.0234(7) 0.0233(6) 0.0251(7) 0.0035(5) 0.0084(5) 0.0023(5) C7 0.0323(8) 0.0256(7) 0.0321(8) -0.0025(6) 0.0111(6) 0.0000(6) C8 0.0401(10) 0.0235(7) 0.0455(10) -0.0001(7) 0.0169(8) 0.0005(7) C9 0.0416(10) 0.0270(8) 0.0419(10) 0.0091(7) 0.0162(8) 0.0075(7) C10 0.0322(8) 0.0277(7) 0.0320(8) 0.0073(6) 0.0103(6) 0.0055(6) C11 0.0250(7) 0.0237(6) 0.0254(7) 0.0030(5) 0.0094(6) 0.0023(5) C12 0.0227(7) 0.0247(6) 0.0225(7) 0.0035(5) 0.0059(5) 0.0038(5) C13 0.0288(8) 0.0296(7) 0.0265(7) 0.0064(6) 0.0113(6) 0.0034(6) C14 0.0274(7) 0.0254(7) 0.0283(7) 0.0027(6) 0.0095(6) 0.0006(6) C15 0.0367(9) 0.0330(8) 0.0251(7) 0.0044(6) 0.0134(7) 0.0007(7) C16 0.0437(10) 0.0385(9) 0.0253(8) 0.0077(7) 0.0084(7) 0.0074(8) C17 0.0591(13) 0.0400(10) 0.0306(9) 0.0045(7) 0.0159(9) 0.0150(9) C18 0.0611(13) 0.0393(10) 0.0231(8) 0.0034(7) 0.0108(8) -0.0010(9) C19 0.0401(10) 0.0433(10) 0.0307(9) 0.0122(7) 0.0019(7) -0.0032(8) C20 0.0333(9) 0.0388(9) 0.0386(9) 0.0115(7) 0.0120(7) 0.0061(7) C21 0.0431(10) 0.0232(7) 0.0340(8) -0.0011(6) 0.0183(7) -0.0035(7) C22 0.0418(10) 0.0316(8) 0.0343(9) -0.0031(7) 0.0149(8) -0.0023(7) C23 0.0437(11) 0.0364(9) 0.0469(11) -0.0008(8) 0.0244(9) -0.0046(8) C24 0.0595(13) 0.0385(10) 0.0445(11) 0.0073(8) 0.0281(10) -0.0008(9) C25 0.0568(13) 0.0356(9) 0.0430(11) 0.0099(8) 0.0196(10) 0.0069(9) C26 0.0413(10) 0.0278(8) 0.0435(10) 0.0045(7) 0.0176(8) 0.0021(7) N1S 0.102(2) 0.0709(18) 0.085(2) -0.0087(16) 0.0065(19) 0.0115(17) C1S 0.080(2) 0.082(2) 0.0505(15) -0.0066(14) 0.0084(15) 0.0357(18) C2S 0.095(3) 0.138(4) 0.067(2) 0.024(2) 0.0368(19) 0.061(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N1 1.9428(15) . ? Fe1 N1 1.9428(15) 2_666 ? Fe1 N2 1.9845(14) 2_666 ? Fe1 N2 1.9845(14) . ? Fe1 N3 1.9887(14) . ? Fe1 N3 1.9887(14) 2_666 ? S1 C1 1.6301(17) . ? F1 C16 1.327(2) . ? F2 C17 1.332(2) . ? F3 C18 1.339(2) . ? F4 C19 1.336(2) . ? F5 C20 1.338(2) . ? F6 C22 1.334(2) . ? F7 C23 1.333(2) . ? F8 C24 1.336(2) . ? F9 C25 1.341(3) . ? F10 C26 1.332(2) . ? O1 C13 1.3606(18) . ? O1 C15 1.382(2) . ? O2 C14 1.3590(19) . ? O2 C21 1.387(2) . ? N1 C1 1.161(2) . ? N2 C6 1.342(2) . ? N2 C2 1.3503(19) . ? N3 C11 1.340(2) . ? N3 C7 1.354(2) . ? N4 C12 1.367(2) . ? N4 C11 1.4239(19) . ? N4 C6 1.4332(18) . ? N5 C13 1.320(2) . ? N5 C12 1.3306(19) . ? N6 C14 1.310(2) . ? N6 C12 1.338(2) . ? N7 C13 1.318(2) . ? N7 C14 1.325(2) . ? C2 C3 1.375(2) . ? C2 H2A 0.9500 . ? C3 C4 1.386(3) . ? C3 H3A 0.9500 . ? C4 C5 1.385(2) . ? C4 H4A 0.9500 . ? C5 C6 1.388(2) . ? C5 H5A 0.9500 . ? C7 C8 1.378(3) . ? C7 H7A 0.9500 . ? C8 C9 1.381(3) . ? C8 H8A 0.9500 . ? C9 C10 1.378(3) . ? C9 H9A 0.9500 . ? C10 C11 1.389(2) . ? C10 H10A 0.9500 . ? C15 C20 1.380(3) . ? C15 C16 1.380(3) . ? C16 C17 1.371(3) . ? C17 C18 1.378(3) . ? C18 C19 1.369(3) . ? C19 C20 1.376(3) . ? C21 C22 1.375(3) . ? C21 C26 1.380(3) . ? C22 C23 1.384(3) . ? C23 C24 1.372(3) . ? C24 C25 1.371(3) . ? C25 C26 1.374(3) . ? N1S C1S 1.151(5) . ? C1S C2S 1.456(6) . ? C2S H2S1 0.9800 . ? C2S H2S2 0.9800 . ? C2S H2S3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 180.00(8) . 2_666 ? N1 Fe1 N2 87.93(6) . 2_666 ? N1 Fe1 N2 92.07(6) 2_666 2_666 ? N1 Fe1 N2 92.07(6) . . ? N1 Fe1 N2 87.93(6) 2_666 . ? N2 Fe1 N2 180.0 2_666 . ? N1 Fe1 N3 91.72(6) . . ? N1 Fe1 N3 88.28(6) 2_666 . ? N2 Fe1 N3 93.81(5) 2_666 . ? N2 Fe1 N3 86.19(5) . . ? N1 Fe1 N3 88.28(6) . 2_666 ? N1 Fe1 N3 91.72(6) 2_666 2_666 ? N2 Fe1 N3 86.19(5) 2_666 2_666 ? N2 Fe1 N3 93.81(5) . 2_666 ? N3 Fe1 N3 180.0 . 2_666 ? C13 O1 C15 118.26(14) . . ? C14 O2 C21 115.61(13) . . ? C1 N1 Fe1 176.32(14) . . ? C6 N2 C2 117.27(14) . . ? C6 N2 Fe1 122.02(10) . . ? C2 N2 Fe1 120.58(11) . . ? C11 N3 C7 117.33(14) . . ? C11 N3 Fe1 122.00(10) . . ? C7 N3 Fe1 120.67(12) . . ? C12 N4 C11 122.15(13) . . ? C12 N4 C6 120.55(13) . . ? C11 N4 C6 117.28(12) . . ? C13 N5 C12 112.64(14) . . ? C14 N6 C12 113.52(14) . . ? C13 N7 C14 110.53(14) . . ? N1 C1 S1 178.95(16) . . ? N2 C2 C3 122.97(15) . . ? N2 C2 H2A 118.5 . . ? C3 C2 H2A 118.5 . . ? C2 C3 C4 119.16(15) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C5 C4 C3 118.81(15) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C4 C5 C6 118.45(15) . . ? C4 C5 H5A 120.8 . . ? C6 C5 H5A 120.8 . . ? N2 C6 C5 123.27(14) . . ? N2 C6 N4 116.70(13) . . ? C5 C6 N4 120.00(14) . . ? N3 C7 C8 122.52(17) . . ? N3 C7 H7A 118.7 . . ? C8 C7 H7A 118.7 . . ? C7 C8 C9 119.15(16) . . ? C7 C8 H8A 120.4 . . ? C9 C8 H8A 120.4 . . ? C10 C9 C8 119.20(16) . . ? C10 C9 H9A 120.4 . . ? C8 C9 H9A 120.4 . . ? C9 C10 C11 118.34(17) . . ? C9 C10 H10A 120.8 . . ? C11 C10 H10A 120.8 . . ? N3 C11 C10 123.24(15) . . ? N3 C11 N4 116.42(13) . . ? C10 C11 N4 120.24(15) . . ? N5 C12 N6 125.23(15) . . ? N5 C12 N4 118.81(14) . . ? N6 C12 N4 115.95(13) . . ? N7 C13 N5 129.43(15) . . ? N7 C13 O1 117.86(15) . . ? N5 C13 O1 112.70(14) . . ? N6 C14 N7 128.63(15) . . ? N6 C14 O2 117.96(14) . . ? N7 C14 O2 113.41(14) . . ? C20 C15 C16 118.47(17) . . ? C20 C15 O1 118.73(17) . . ? C16 C15 O1 122.38(16) . . ? F1 C16 C17 119.15(18) . . ? F1 C16 C15 120.07(17) . . ? C17 C16 C15 120.77(17) . . ? F2 C17 C16 120.28(18) . . ? F2 C17 C18 119.62(19) . . ? C16 C17 C18 120.10(19) . . ? F3 C18 C19 120.30(19) . . ? F3 C18 C17 119.9(2) . . ? C19 C18 C17 119.77(18) . . ? F4 C19 C18 119.37(19) . . ? F4 C19 C20 120.7(2) . . ? C18 C19 C20 119.93(17) . . ? F5 C20 C19 119.32(18) . . ? F5 C20 C15 119.74(19) . . ? C19 C20 C15 120.94(18) . . ? C22 C21 C26 119.26(17) . . ? C22 C21 O2 119.42(18) . . ? C26 C21 O2 121.24(17) . . ? F6 C22 C21 120.23(17) . . ? F6 C22 C23 119.34(19) . . ? C21 C22 C23 120.43(19) . . ? F7 C23 C24 120.26(19) . . ? F7 C23 C22 120.2(2) . . ? C24 C23 C22 119.5(2) . . ? F8 C24 C25 119.5(2) . . ? F8 C24 C23 120.0(2) . . ? C25 C24 C23 120.46(19) . . ? F9 C25 C24 120.02(19) . . ? F9 C25 C26 120.1(2) . . ? C24 C25 C26 119.8(2) . . ? F10 C26 C25 119.4(2) . . ? F10 C26 C21 120.09(17) . . ? C25 C26 C21 120.50(19) . . ? N1S C1S C2S 178.4(4) . . ? C1S C2S H2S1 109.5 . . ? C1S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? C1S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.439 _refine_diff_density_min -0.650 _refine_diff_density_rms 0.093 data_9acn4a _database_code_depnum_ccdc_archive 'CCDC 921067' #TrackingRef '17083_web_deposit_cif_file_6_OlivierRoubeau_1358848554.Cpd3-9acn4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H16 F20 Fe N14 O4 S2, 2(C2 H3 N)' _chemical_formula_sum 'C56 H22 F20 Fe N16 O4 S2' _chemical_formula_weight 1482.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0020 0.0020 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' H H 0.0000 0.0000 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' N N -0.0031 0.0040 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' O O -0.0041 0.0074 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' F F -0.0053 0.0125 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' S S 0.1206 0.1480 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Fe Fe 0.2064 0.9930 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.643(2) _cell_length_b 11.494(2) _cell_length_c 15.844(3) _cell_angle_alpha 94.851(2) _cell_angle_beta 100.035(2) _cell_angle_gamma 100.981(2) _cell_volume 1510.2(5) _cell_formula_units_Z 1 _cell_measurement_temperature 280(2) _cell_measurement_reflns_used 5627 _cell_measurement_theta_min 3.64 _cell_measurement_theta_max 30.43 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 0.554 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details 'SADABS Bruker AXS Madison WI US' _exptl_special_details ; ? ; _diffrn_ambient_temperature 280(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17781 _diffrn_reflns_av_R_equivalents 0.0540 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 30.65 _reflns_number_total 7059 _reflns_number_gt 5028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.68a' _computing_data_reduction 'Bruker SAINT v7.68a' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogens were refined anisotropically. Three F atoms as well as the methyl C of the lattice acetonitrile molecule were refined with displacement parameters restraints. Hydrogens were placed geometrically on their carrier atom and refined with a riding model. ; _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^)+(0.1401P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.163(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7059 _refine_ls_number_parameters 450 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.2027 _refine_ls_wR_factor_gt 0.1839 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.5000 0.5000 0.5000 0.0459(2) Uani 1 2 d S . . S1 S 0.42084(11) 0.69912(10) 0.76466(5) 0.0820(3) Uani 1 1 d . . . F1 F 0.5177(3) 0.6958(2) 0.97082(12) 0.0873(6) Uani 1 1 d . . . F2 F 0.5324(4) 0.7888(3) 1.13377(18) 0.1289(11) Uani 1 1 d . . . F3 F 0.7161(5) 0.7166(3) 1.26585(13) 0.1303(11) Uani 1 1 d . . . F4 F 0.8900(3) 0.5529(3) 1.23447(16) 0.1217(11) Uani 1 1 d . . . F5 F 0.8781(3) 0.4589(3) 1.07013(19) 0.1086(8) Uani 1 1 d . . . F6 F 1.2828(3) 0.9057(2) 0.86170(13) 0.0852(6) Uani 1 1 d . . . F7 F 1.4128(3) 1.0083(2) 0.73623(18) 0.1071(8) Uani 1 1 d . . . F8 F 1.2185(4) 1.0592(3) 0.59685(17) 0.1227(10) Uani 1 1 d . . . F9 F 0.8969(4) 1.0049(3) 0.58166(17) 0.1142(9) Uani 1 1 d . . . F10 F 0.7682(3) 0.90224(19) 0.70703(15) 0.0857(6) Uani 1 1 d . . . O1 O 0.6826(3) 0.51819(18) 0.93543(13) 0.0668(6) Uani 1 1 d . . . O2 O 0.9596(3) 0.85048(17) 0.85206(12) 0.0631(5) Uani 1 1 d . . . N1 N 0.4643(3) 0.5809(3) 0.61377(15) 0.0630(6) Uani 1 1 d . . . N2 N 0.7551(2) 0.58803(19) 0.52915(13) 0.0478(5) Uani 1 1 d . . . N3 N 0.5947(3) 0.36086(19) 0.56799(14) 0.0519(5) Uani 1 1 d . . . N4 N 0.7829(2) 0.50939(17) 0.66279(12) 0.0429(4) Uani 1 1 d . . . N5 N 0.7283(3) 0.51060(19) 0.80124(13) 0.0489(5) Uani 1 1 d . . . N6 N 0.8727(3) 0.68201(18) 0.75532(13) 0.0467(5) Uani 1 1 d . . . N7 N 0.8243(3) 0.68948(19) 0.89842(13) 0.0515(5) Uani 1 1 d . . . C1 C 0.4458(3) 0.6301(3) 0.67657(17) 0.0543(6) Uani 1 1 d . . . C2 C 0.8203(3) 0.6459(3) 0.46960(18) 0.0594(7) Uani 1 1 d . . . H2A H 0.7529 0.6547 0.4190 0.071 Uiso 1 1 calc R . . C3 C 0.9818(3) 0.6929(3) 0.47985(19) 0.0603(7) Uani 1 1 d . . . H3A H 1.0223 0.7356 0.4383 0.072 Uiso 1 1 calc R . . C4 C 1.0821(3) 0.6753(3) 0.55278(18) 0.0566(6) Uani 1 1 d . . . H4A H 1.1922 0.7053 0.5610 0.068 Uiso 1 1 calc R . . C5 C 1.0189(3) 0.6132(2) 0.61368(17) 0.0495(6) Uani 1 1 d . . . H5A H 1.0849 0.5989 0.6630 0.059 Uiso 1 1 calc R . . C6 C 0.8542(3) 0.5727(2) 0.59940(15) 0.0426(5) Uani 1 1 d . . . C7 C 0.5311(4) 0.2451(3) 0.5398(2) 0.0648(8) Uani 1 1 d . . . H7A H 0.4580 0.2253 0.4877 0.078 Uiso 1 1 calc R . . C8 C 0.5705(4) 0.1551(3) 0.5856(2) 0.0734(9) Uani 1 1 d . . . H8A H 0.5234 0.0758 0.5651 0.088 Uiso 1 1 calc R . . C9 C 0.6801(4) 0.1834(3) 0.6621(2) 0.0713(9) Uani 1 1 d . . . H9A H 0.7061 0.1238 0.6946 0.086 Uiso 1 1 calc R . . C10 C 0.7509(4) 0.3014(2) 0.68976(19) 0.0571(6) Uani 1 1 d . . . H10A H 0.8274 0.3229 0.7406 0.068 Uiso 1 1 calc R . . C11 C 0.7055(3) 0.3870(2) 0.64020(16) 0.0467(5) Uani 1 1 d . . . C12 C 0.7948(3) 0.5686(2) 0.74290(15) 0.0420(5) Uani 1 1 d . . . C13 C 0.7492(3) 0.5775(2) 0.87550(16) 0.0501(6) Uani 1 1 d . . . C14 C 0.8811(3) 0.7342(2) 0.83306(15) 0.0476(5) Uani 1 1 d . . . C15 C 0.6995(3) 0.5766(3) 1.01714(17) 0.0565(6) Uani 1 1 d . . . C16 C 0.6127(4) 0.6610(3) 1.03483(18) 0.0623(7) Uani 1 1 d . . . C17 C 0.6184(5) 0.7070(3) 1.1182(2) 0.0787(10) Uani 1 1 d . . . C18 C 0.7103(5) 0.6703(4) 1.1846(2) 0.0813(11) Uani 1 1 d . . . C19 C 0.7973(4) 0.5870(4) 1.1689(2) 0.0794(11) Uani 1 1 d . . . C20 C 0.7926(4) 0.5402(3) 1.0850(2) 0.0697(8) Uani 1 1 d . . . C21 C 1.0235(4) 0.9000(2) 0.78581(19) 0.0607(7) Uani 1 1 d . . . C22 C 1.1874(4) 0.9279(3) 0.7930(2) 0.0670(8) Uani 1 1 d . . . C23 C 1.2536(5) 0.9815(3) 0.7290(2) 0.0791(10) Uani 1 1 d . . . C24 C 1.1544(6) 1.0062(3) 0.6587(3) 0.0855(11) Uani 1 1 d . . . C25 C 0.9937(5) 0.9790(3) 0.6507(2) 0.0804(10) Uani 1 1 d . . . C26 C 0.9267(4) 0.9273(3) 0.7151(2) 0.0691(8) Uani 1 1 d . . . N1S N 0.9431(10) 0.1632(5) 0.8554(6) 0.165(3) Uani 1 1 d . . . C1S C 0.8569(10) 0.1129(9) 0.8909(4) 0.140(3) Uani 1 1 d . . . C2S C 0.7473(10) 0.0361(9) 0.9361(5) 0.184(3) Uani 1 1 d U . . H2S1 H 0.6767 -0.0261 0.8951 0.276 Uiso 1 1 calc R . . H2S2 H 0.6849 0.0837 0.9628 0.276 Uiso 1 1 calc R . . H2S3 H 0.8094 0.0012 0.9795 0.276 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 0.0385(3) 0.0594(3) 0.0375(3) -0.0013(2) 0.00831(19) 0.0068(2) S1 0.0719(5) 0.1166(8) 0.0553(5) -0.0218(4) 0.0100(4) 0.0306(5) F1 0.1065(16) 0.1035(15) 0.0583(11) 0.0192(10) 0.0070(10) 0.0418(13) F2 0.195(3) 0.122(2) 0.0892(17) -0.0039(15) 0.0442(19) 0.075(2) F3 0.209(3) 0.1161(19) 0.0435(11) -0.0019(11) 0.0155(15) -0.007(2) F4 0.1063(18) 0.150(2) 0.0882(16) 0.0603(17) -0.0241(14) -0.0054(16) F5 0.0922(16) 0.1220(19) 0.134(2) 0.0506(17) 0.0406(15) 0.0467(15) F6 0.0856(14) 0.0978(15) 0.0677(12) 0.0020(10) 0.0207(10) 0.0062(11) F7 0.0880(16) 0.1152(18) 0.1154(19) 0.0120(14) 0.0502(14) -0.0119(13) F8 0.142(2) 0.135(2) 0.1003(18) 0.0501(16) 0.0653(17) -0.0007(17) F9 0.141(2) 0.122(2) 0.0927(17) 0.0485(15) 0.0355(16) 0.0320(17) F10 0.0820(14) 0.0829(13) 0.0968(15) 0.0245(11) 0.0274(11) 0.0134(10) O1 0.0873(15) 0.0595(11) 0.0550(11) 0.0100(9) 0.0363(11) -0.0030(10) O2 0.0823(14) 0.0494(10) 0.0526(10) -0.0026(8) 0.0291(10) -0.0093(9) N1 0.0541(13) 0.0877(17) 0.0453(12) -0.0040(11) 0.0067(10) 0.0182(12) N2 0.0432(10) 0.0594(12) 0.0414(10) 0.0097(9) 0.0128(8) 0.0067(9) N3 0.0497(11) 0.0517(11) 0.0509(12) -0.0029(9) 0.0143(9) 0.0023(9) N4 0.0421(10) 0.0454(10) 0.0400(10) 0.0069(8) 0.0108(8) 0.0028(8) N5 0.0515(11) 0.0501(11) 0.0471(11) 0.0096(8) 0.0190(9) 0.0050(9) N6 0.0521(11) 0.0467(10) 0.0407(10) 0.0056(8) 0.0144(8) 0.0036(9) N7 0.0553(12) 0.0555(12) 0.0431(11) 0.0074(9) 0.0158(9) 0.0043(10) C1 0.0427(12) 0.0750(17) 0.0446(13) 0.0018(12) 0.0057(10) 0.0154(12) C2 0.0564(15) 0.0806(19) 0.0468(14) 0.0205(13) 0.0186(11) 0.0148(13) C3 0.0581(16) 0.0693(17) 0.0619(16) 0.0201(13) 0.0299(13) 0.0120(13) C4 0.0431(13) 0.0671(16) 0.0614(16) 0.0102(12) 0.0214(12) 0.0049(11) C5 0.0421(12) 0.0589(14) 0.0476(13) 0.0086(11) 0.0107(10) 0.0081(10) C6 0.0424(11) 0.0453(11) 0.0413(11) 0.0058(9) 0.0141(9) 0.0062(9) C7 0.0637(17) 0.0545(15) 0.0683(18) -0.0120(13) 0.0192(14) -0.0044(13) C8 0.083(2) 0.0446(14) 0.089(2) -0.0070(14) 0.0359(19) -0.0052(14) C9 0.085(2) 0.0486(15) 0.088(2) 0.0153(15) 0.0354(19) 0.0131(14) C10 0.0634(16) 0.0515(14) 0.0587(16) 0.0108(11) 0.0195(13) 0.0093(12) C11 0.0442(12) 0.0472(12) 0.0493(13) 0.0029(10) 0.0180(10) 0.0043(10) C12 0.0373(11) 0.0455(12) 0.0427(11) 0.0080(9) 0.0088(9) 0.0053(9) C13 0.0508(13) 0.0553(14) 0.0468(13) 0.0147(10) 0.0184(10) 0.0059(11) C14 0.0500(13) 0.0473(12) 0.0444(12) 0.0048(9) 0.0139(10) 0.0033(10) C15 0.0612(16) 0.0622(15) 0.0462(13) 0.0115(11) 0.0218(12) 0.0004(12) C16 0.0712(18) 0.0699(18) 0.0440(14) 0.0109(12) 0.0108(13) 0.0089(14) C17 0.108(3) 0.076(2) 0.0549(17) 0.0041(15) 0.0274(18) 0.0188(19) C18 0.105(3) 0.086(2) 0.0416(15) 0.0100(15) 0.0119(16) -0.006(2) C19 0.076(2) 0.092(2) 0.0582(18) 0.0324(17) -0.0023(16) -0.0093(19) C20 0.0597(17) 0.078(2) 0.074(2) 0.0268(16) 0.0208(15) 0.0070(15) C21 0.081(2) 0.0433(13) 0.0564(15) -0.0001(11) 0.0307(14) -0.0031(12) C22 0.078(2) 0.0592(16) 0.0599(17) -0.0004(13) 0.0238(15) -0.0006(14) C23 0.084(2) 0.0701(19) 0.083(2) 0.0040(17) 0.044(2) -0.0075(17) C24 0.114(3) 0.071(2) 0.079(2) 0.0186(17) 0.051(2) 0.003(2) C25 0.111(3) 0.0659(19) 0.072(2) 0.0231(16) 0.032(2) 0.0173(19) C26 0.083(2) 0.0514(15) 0.075(2) 0.0101(13) 0.0306(17) 0.0057(14) N1S 0.181(7) 0.103(4) 0.187(7) -0.011(4) 0.002(5) 0.012(4) C1S 0.140(6) 0.189(8) 0.091(4) -0.013(4) 0.016(4) 0.059(6) C2S 0.196(6) 0.261(8) 0.127(5) 0.036(5) 0.066(5) 0.090(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N1 2.056(2) 2_666 ? Fe1 N1 2.056(2) . ? Fe1 N2 2.194(2) . ? Fe1 N2 2.194(2) 2_666 ? Fe1 N3 2.207(2) 2_666 ? Fe1 N3 2.207(2) . ? S1 C1 1.615(3) . ? F1 C16 1.329(3) . ? F2 C17 1.338(5) . ? F3 C18 1.339(4) . ? F4 C19 1.332(4) . ? F5 C20 1.327(4) . ? F6 C22 1.321(4) . ? F7 C23 1.334(4) . ? F8 C24 1.341(4) . ? F9 C25 1.349(5) . ? F10 C26 1.325(4) . ? O1 C13 1.359(3) . ? O1 C15 1.377(3) . ? O2 C14 1.361(3) . ? O2 C21 1.383(3) . ? N1 C1 1.154(4) . ? N2 C6 1.327(3) . ? N2 C2 1.341(3) . ? N3 C11 1.329(3) . ? N3 C7 1.344(3) . ? N4 C12 1.366(3) . ? N4 C11 1.424(3) . ? N4 C6 1.445(3) . ? N5 C13 1.314(3) . ? N5 C12 1.332(3) . ? N6 C14 1.308(3) . ? N6 C12 1.329(3) . ? N7 C13 1.316(3) . ? N7 C14 1.322(3) . ? C2 C3 1.374(4) . ? C2 H2A 0.9300 . ? C3 C4 1.373(4) . ? C3 H3A 0.9300 . ? C4 C5 1.375(3) . ? C4 H4A 0.9300 . ? C5 C6 1.383(3) . ? C5 H5A 0.9300 . ? C7 C8 1.374(5) . ? C7 H7A 0.9300 . ? C8 C9 1.373(5) . ? C8 H8A 0.9300 . ? C9 C10 1.377(4) . ? C9 H9A 0.9300 . ? C10 C11 1.381(4) . ? C10 H10A 0.9300 . ? C15 C20 1.372(4) . ? C15 C16 1.374(5) . ? C16 C17 1.369(4) . ? C17 C18 1.352(5) . ? C18 C19 1.358(6) . ? C19 C20 1.381(5) . ? C21 C26 1.374(5) . ? C21 C22 1.374(5) . ? C22 C23 1.382(4) . ? C23 C24 1.368(6) . ? C24 C25 1.346(6) . ? C25 C26 1.381(4) . ? N1S C1S 1.114(9) . ? C1S C2S 1.488(12) . ? C2S H2S1 0.9600 . ? C2S H2S2 0.9600 . ? C2S H2S3 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 180.00(12) 2_666 . ? N1 Fe1 N2 88.77(9) 2_666 . ? N1 Fe1 N2 91.23(9) . . ? N1 Fe1 N2 91.23(9) 2_666 2_666 ? N1 Fe1 N2 88.77(9) . 2_666 ? N2 Fe1 N2 179.999(1) . 2_666 ? N1 Fe1 N3 90.96(9) 2_666 2_666 ? N1 Fe1 N3 89.04(9) . 2_666 ? N2 Fe1 N3 98.17(8) . 2_666 ? N2 Fe1 N3 81.83(8) 2_666 2_666 ? N1 Fe1 N3 89.04(9) 2_666 . ? N1 Fe1 N3 90.96(9) . . ? N2 Fe1 N3 81.83(8) . . ? N2 Fe1 N3 98.17(8) 2_666 . ? N3 Fe1 N3 179.998(1) 2_666 . ? C13 O1 C15 119.0(2) . . ? C14 O2 C21 115.3(2) . . ? C1 N1 Fe1 177.6(3) . . ? C6 N2 C2 117.4(2) . . ? C6 N2 Fe1 122.12(15) . . ? C2 N2 Fe1 119.81(18) . . ? C11 N3 C7 118.0(2) . . ? C11 N3 Fe1 122.26(17) . . ? C7 N3 Fe1 119.6(2) . . ? C12 N4 C11 122.34(18) . . ? C12 N4 C6 118.72(19) . . ? C11 N4 C6 118.93(19) . . ? C13 N5 C12 112.6(2) . . ? C14 N6 C12 113.2(2) . . ? C13 N7 C14 110.3(2) . . ? N1 C1 S1 179.7(2) . . ? N2 C2 C3 123.1(3) . . ? N2 C2 H2A 118.5 . . ? C3 C2 H2A 118.5 . . ? C4 C3 C2 118.4(2) . . ? C4 C3 H3A 120.8 . . ? C2 C3 H3A 120.8 . . ? C3 C4 C5 119.6(2) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C4 C5 C6 118.0(2) . . ? C4 C5 H5A 121.0 . . ? C6 C5 H5A 121.0 . . ? N2 C6 C5 123.4(2) . . ? N2 C6 N4 117.0(2) . . ? C5 C6 N4 119.6(2) . . ? N3 C7 C8 122.1(3) . . ? N3 C7 H7A 118.9 . . ? C8 C7 H7A 118.9 . . ? C9 C8 C7 119.3(3) . . ? C9 C8 H8A 120.3 . . ? C7 C8 H8A 120.3 . . ? C8 C9 C10 119.1(3) . . ? C8 C9 H9A 120.5 . . ? C10 C9 H9A 120.5 . . ? C9 C10 C11 118.3(3) . . ? C9 C10 H10A 120.8 . . ? C11 C10 H10A 120.8 . . ? N3 C11 C10 123.1(2) . . ? N3 C11 N4 116.3(2) . . ? C10 C11 N4 120.6(2) . . ? N6 C12 N5 125.4(2) . . ? N6 C12 N4 115.77(19) . . ? N5 C12 N4 118.8(2) . . ? N5 C13 N7 129.4(2) . . ? N5 C13 O1 112.7(2) . . ? N7 C13 O1 117.8(2) . . ? N6 C14 N7 129.0(2) . . ? N6 C14 O2 117.5(2) . . ? N7 C14 O2 113.5(2) . . ? C20 C15 C16 118.3(3) . . ? C20 C15 O1 118.9(3) . . ? C16 C15 O1 122.4(3) . . ? F1 C16 C17 119.3(3) . . ? F1 C16 C15 119.9(3) . . ? C17 C16 C15 120.8(3) . . ? F2 C17 C18 119.9(3) . . ? F2 C17 C16 119.7(3) . . ? C18 C17 C16 120.4(4) . . ? F3 C18 C17 120.0(4) . . ? F3 C18 C19 120.1(4) . . ? C17 C18 C19 119.9(3) . . ? F4 C19 C18 119.7(4) . . ? F4 C19 C20 120.3(4) . . ? C18 C19 C20 120.1(3) . . ? F5 C20 C15 119.8(3) . . ? F5 C20 C19 119.7(3) . . ? C15 C20 C19 120.5(3) . . ? C26 C21 C22 119.4(3) . . ? C26 C21 O2 121.3(3) . . ? C22 C21 O2 119.2(3) . . ? F6 C22 C21 120.4(3) . . ? F6 C22 C23 119.5(3) . . ? C21 C22 C23 120.1(3) . . ? F7 C23 C24 120.8(3) . . ? F7 C23 C22 119.9(4) . . ? C24 C23 C22 119.3(3) . . ? F8 C24 C25 119.4(4) . . ? F8 C24 C23 119.4(4) . . ? C25 C24 C23 121.1(3) . . ? C24 C25 F9 120.7(3) . . ? C24 C25 C26 119.9(4) . . ? F9 C25 C26 119.3(4) . . ? F10 C26 C21 120.5(3) . . ? F10 C26 C25 119.3(3) . . ? C21 C26 C25 120.1(3) . . ? N1S C1S C2S 174.9(10) . . ? C1S C2S H2S1 109.5 . . ? C1S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? C1S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.390 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.109 data_17ch2cl2 _database_code_depnum_ccdc_archive 'CCDC 922570' #TrackingRef 'web_deposit_cif_file_0_OlivierRoubeau_1359564483.L1-17ch2cl2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H18 N6 O2' _chemical_formula_sum 'C25 H18 N6 O2' _chemical_formula_weight 434.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0020 0.0020 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' H H 0.0000 0.0000 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' N N -0.0031 0.0040 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' O O -0.0041 0.0074 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.840(2) _cell_length_b 11.894(2) _cell_length_c 18.623(3) _cell_angle_alpha 100.603(2) _cell_angle_beta 105.797(2) _cell_angle_gamma 104.495(2) _cell_volume 2153.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 5716 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 28.21 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS Bruker AXS Madison WI US' _exptl_special_details ; ? ; _diffrn_ambient_temperature 250(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21045 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0703 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.97 _reflns_number_total 8727 _reflns_number_gt 6343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogens were refined anisotropically. Hydrogens were found in a difference Fourier map, placed geometrically on their carrier atom and refined with a riding model. ; _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^)+(0.0856P)^2^+0.0126P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8727 _refine_ls_number_parameters 595 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1553 _refine_ls_wR_factor_gt 0.1407 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 O1 O 0.13379(12) 0.29910(10) -0.12315(6) 0.0485(3) Uani 1 1 d . . . O2 O 0.43925(13) 0.51522(11) 0.11651(7) 0.0519(3) Uani 1 1 d . . . N1 N -0.04875(16) 0.73287(15) -0.05266(9) 0.0559(4) Uani 1 1 d . . . N2 N 0.26335(17) 0.87612(13) 0.04156(9) 0.0554(4) Uani 1 1 d . . . N3 N 0.13751(14) 0.67340(12) -0.00937(7) 0.0424(3) Uani 1 1 d . . . N4 N 0.12698(14) 0.48021(12) -0.06847(8) 0.0427(3) Uani 1 1 d . . . N5 N 0.29097(14) 0.59369(12) 0.05517(8) 0.0436(3) Uani 1 1 d . . . N6 N 0.28973(14) 0.39888(12) -0.00319(8) 0.0431(3) Uani 1 1 d . . . C1 C -0.1435(2) 0.7493(2) -0.10916(13) 0.0692(6) Uani 1 1 d . . . H1A H -0.2046 0.7854 -0.0953 0.083 Uiso 1 1 calc R . . C2 C -0.1566(2) 0.7167(2) -0.18563(13) 0.0679(6) Uani 1 1 d . . . H2A H -0.2248 0.7301 -0.2234 0.082 Uiso 1 1 calc R . . C3 C -0.0681(2) 0.66390(18) -0.20615(11) 0.0594(5) Uani 1 1 d . . . H3A H -0.0745 0.6409 -0.2584 0.071 Uiso 1 1 calc R . . C4 C 0.03026(19) 0.64474(16) -0.14960(10) 0.0487(4) Uani 1 1 d . . . H4A H 0.0918 0.6080 -0.1622 0.058 Uiso 1 1 calc R . . C5 C 0.03537(16) 0.68140(14) -0.07376(9) 0.0416(4) Uani 1 1 d . . . C6 C 0.3167(2) 0.97678(18) 0.10072(15) 0.0729(6) Uani 1 1 d . . . H6A H 0.3649 1.0481 0.0925 0.087 Uiso 1 1 calc R . . C7 C 0.3046(3) 0.9809(2) 0.17253(14) 0.0795(7) Uani 1 1 d . . . H7A H 0.3436 1.0534 0.2124 0.095 Uiso 1 1 calc R . . C8 C 0.2349(3) 0.8778(2) 0.18521(12) 0.0762(7) Uani 1 1 d . . . H8A H 0.2259 0.8783 0.2341 0.091 Uiso 1 1 calc R . . C9 C 0.1784(2) 0.77418(18) 0.12587(11) 0.0575(5) Uani 1 1 d . . . H9A H 0.1289 0.7021 0.1325 0.069 Uiso 1 1 calc R . . C10 C 0.19635(17) 0.77907(15) 0.05613(9) 0.0439(4) Uani 1 1 d . . . C11 C 0.18600(16) 0.57882(14) -0.00807(9) 0.0403(4) Uani 1 1 d . . . C12 C 0.18603(17) 0.39688(14) -0.06164(9) 0.0408(4) Uani 1 1 d . . . C13 C 0.33458(17) 0.49991(15) 0.05281(9) 0.0412(4) Uani 1 1 d . . . C14 C 0.19593(19) 0.20867(14) -0.11907(9) 0.0460(4) Uani 1 1 d . . . C15 C 0.3131(2) 0.22222(18) -0.13602(11) 0.0564(5) Uani 1 1 d . . . H15A H 0.3500 0.2894 -0.1522 0.068 Uiso 1 1 calc R . . C16 C 0.3756(3) 0.1357(2) -0.12896(13) 0.0725(6) Uani 1 1 d . . . H16A H 0.4570 0.1441 -0.1395 0.087 Uiso 1 1 calc R . . C17 C 0.3197(3) 0.0372(2) -0.10658(13) 0.0801(8) Uani 1 1 d . . . H17A H 0.3638 -0.0209 -0.1006 0.096 Uiso 1 1 calc R . . C18 C 0.1990(3) 0.02318(19) -0.09275(13) 0.0796(8) Uani 1 1 d . . . H18A H 0.1596 -0.0461 -0.0792 0.095 Uiso 1 1 calc R . . C19 C 0.1351(2) 0.10995(17) -0.09853(11) 0.0607(5) Uani 1 1 d . . . H19A H 0.0531 0.1014 -0.0887 0.073 Uiso 1 1 calc R . . C20 C 0.49875(16) 0.42580(14) 0.12884(9) 0.0412(4) Uani 1 1 d . . . C21 C 0.53038(18) 0.35615(17) 0.07350(10) 0.0491(4) Uani 1 1 d . . . H21A H 0.5071 0.3628 0.0224 0.059 Uiso 1 1 calc R . . C22 C 0.5968(2) 0.27647(18) 0.09432(12) 0.0569(5) Uani 1 1 d . . . H22A H 0.6182 0.2275 0.0570 0.068 Uiso 1 1 calc R . . C23 C 0.6319(2) 0.26800(18) 0.16888(12) 0.0638(6) Uani 1 1 d . . . H23A H 0.6776 0.2135 0.1826 0.077 Uiso 1 1 calc R . . C24 C 0.6010(2) 0.3383(2) 0.22333(12) 0.0687(6) Uani 1 1 d . . . H24A H 0.6257 0.3323 0.2746 0.082 Uiso 1 1 calc R . . C25 C 0.5339(2) 0.41811(18) 0.20370(10) 0.0575(5) Uani 1 1 d . . . H25A H 0.5124 0.4667 0.2412 0.069 Uiso 1 1 calc R . . O3 O 0.66304(13) 0.50214(10) 0.62622(7) 0.0498(3) Uani 1 1 d . . . O4 O 0.64083(13) 0.27284(10) 0.39433(7) 0.0513(3) Uani 1 1 d . . . N7 N 0.98152(16) 0.86348(14) 0.53704(9) 0.0542(4) Uani 1 1 d . . . N8 N 1.09157(16) 0.69469(14) 0.43497(9) 0.0513(4) Uani 1 1 d . . . N9 N 0.92867(14) 0.65597(12) 0.49363(8) 0.0443(3) Uani 1 1 d . . . N10 N 0.79446(14) 0.58073(12) 0.56231(8) 0.0430(3) Uani 1 1 d . . . N11 N 0.78719(15) 0.45952(12) 0.44292(8) 0.0445(3) Uani 1 1 d . . . N12 N 0.64390(14) 0.38005(12) 0.51026(8) 0.0433(3) Uani 1 1 d . . . C26 C 1.0393(2) 0.96694(18) 0.59426(12) 0.0626(5) Uani 1 1 d . . . H26A H 1.0332 1.0391 0.5822 0.075 Uiso 1 1 calc R . . C27 C 1.1064(2) 0.9721(2) 0.66893(12) 0.0662(6) Uani 1 1 d . . . H27A H 1.1428 1.0458 0.7077 0.079 Uiso 1 1 calc R . . C28 C 1.1196(2) 0.8673(2) 0.68634(12) 0.0687(6) Uani 1 1 d . . . H28A H 1.1658 0.8684 0.7373 0.082 Uiso 1 1 calc R . . C29 C 1.0649(2) 0.76156(18) 0.62879(11) 0.0566(5) Uani 1 1 d . . . H29A H 1.0754 0.6892 0.6386 0.068 Uiso 1 1 calc R . . C30 C 0.99423(17) 0.76428(15) 0.55616(9) 0.0442(4) Uani 1 1 d . . . C31 C 1.1271(2) 0.69803(18) 0.37202(12) 0.0577(5) Uani 1 1 d . . . H31A H 1.2196 0.7272 0.3788 0.069 Uiso 1 1 calc R . . C32 C 1.0366(2) 0.66144(19) 0.29811(12) 0.0650(6) Uani 1 1 d . . . H32A H 1.0662 0.6643 0.2553 0.078 Uiso 1 1 calc R . . C33 C 0.9018(2) 0.6205(2) 0.28846(11) 0.0653(6) Uani 1 1 d . . . H33A H 0.8370 0.5946 0.2385 0.078 Uiso 1 1 calc R . . C34 C 0.8621(2) 0.61768(18) 0.35219(10) 0.0544(5) Uani 1 1 d . . . H34A H 0.7701 0.5912 0.3470 0.065 Uiso 1 1 calc R . . C35 C 0.96116(18) 0.65477(15) 0.42399(9) 0.0433(4) Uani 1 1 d . . . C36 C 0.83343(17) 0.56169(14) 0.49960(9) 0.0410(4) Uani 1 1 d . . . C37 C 0.70142(17) 0.48549(15) 0.56272(9) 0.0408(4) Uani 1 1 d . . . C38 C 0.69270(18) 0.37525(14) 0.45208(9) 0.0421(4) Uani 1 1 d . . . C39 C 0.57726(17) 0.40328(15) 0.63921(9) 0.0425(4) Uani 1 1 d . . . C40 C 0.62480(19) 0.37920(16) 0.70883(10) 0.0470(4) Uani 1 1 d . . . H40A H 0.7118 0.4243 0.7437 0.056 Uiso 1 1 calc R . . C41 C 0.5426(2) 0.28752(17) 0.72692(11) 0.0550(5) Uani 1 1 d . . . H41A H 0.5733 0.2709 0.7749 0.066 Uiso 1 1 calc R . . C42 C 0.4172(2) 0.22092(18) 0.67557(13) 0.0610(5) Uani 1 1 d . . . H42A H 0.3629 0.1572 0.6876 0.073 Uiso 1 1 calc R . . C43 C 0.3703(2) 0.2471(2) 0.60607(12) 0.0649(6) Uani 1 1 d . . . H43A H 0.2835 0.2017 0.5711 0.078 Uiso 1 1 calc R . . C44 C 0.45021(19) 0.33981(19) 0.58752(11) 0.0552(5) Uani 1 1 d . . . H44A H 0.4183 0.3589 0.5406 0.066 Uiso 1 1 calc R . . C45 C 0.52388(19) 0.18745(15) 0.39355(9) 0.0481(4) Uani 1 1 d . . . C46 C 0.5337(2) 0.08020(17) 0.40621(12) 0.0606(5) Uani 1 1 d . . . H46A H 0.6165 0.0643 0.4162 0.073 Uiso 1 1 calc R . . C47 C 0.4174(3) -0.00475(19) 0.40386(13) 0.0718(6) Uani 1 1 d . . . H47A H 0.4214 -0.0794 0.4125 0.086 Uiso 1 1 calc R . . C48 C 0.2974(3) 0.0189(2) 0.38917(13) 0.0725(6) Uani 1 1 d . . . H48A H 0.2198 -0.0390 0.3885 0.087 Uiso 1 1 calc R . . C49 C 0.2896(2) 0.1267(2) 0.37537(13) 0.0714(6) Uani 1 1 d . . . H49A H 0.2066 0.1423 0.3648 0.086 Uiso 1 1 calc R . . C50 C 0.4038(2) 0.21215(18) 0.37701(11) 0.0587(5) Uani 1 1 d . . . H50A H 0.3993 0.2859 0.3670 0.070 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 O1 0.0616(7) 0.0381(6) 0.0350(6) 0.0006(5) 0.0027(5) 0.0189(6) O2 0.0628(8) 0.0472(7) 0.0358(6) 0.0002(5) -0.0011(5) 0.0278(6) N1 0.0580(9) 0.0695(10) 0.0473(9) 0.0172(8) 0.0147(7) 0.0344(8) N2 0.0682(10) 0.0404(8) 0.0531(9) 0.0066(7) 0.0151(8) 0.0195(7) N3 0.0523(8) 0.0392(7) 0.0308(7) 0.0047(6) 0.0049(6) 0.0193(6) N4 0.0504(8) 0.0354(7) 0.0347(7) 0.0051(6) 0.0048(6) 0.0145(6) N5 0.0517(8) 0.0403(7) 0.0335(7) 0.0043(6) 0.0057(6) 0.0189(6) N6 0.0531(8) 0.0390(7) 0.0325(7) 0.0052(6) 0.0065(6) 0.0183(6) C1 0.0627(13) 0.0882(16) 0.0635(13) 0.0243(12) 0.0127(10) 0.0417(12) C2 0.0610(12) 0.0788(14) 0.0564(13) 0.0253(11) -0.0002(10) 0.0258(11) C3 0.0665(12) 0.0609(12) 0.0381(10) 0.0131(9) 0.0040(9) 0.0135(10) C4 0.0551(10) 0.0480(10) 0.0371(9) 0.0075(7) 0.0088(8) 0.0167(8) C5 0.0440(9) 0.0384(8) 0.0367(9) 0.0099(7) 0.0061(7) 0.0118(7) C6 0.0802(15) 0.0393(10) 0.0790(16) -0.0018(10) 0.0095(12) 0.0167(10) C7 0.0868(16) 0.0646(14) 0.0594(14) -0.0214(11) -0.0012(12) 0.0328(13) C8 0.0945(17) 0.0839(17) 0.0424(12) -0.0039(11) 0.0124(11) 0.0419(14) C9 0.0702(12) 0.0595(11) 0.0392(10) 0.0056(9) 0.0137(9) 0.0252(10) C10 0.0490(9) 0.0413(9) 0.0364(9) 0.0023(7) 0.0049(7) 0.0217(8) C11 0.0471(9) 0.0383(8) 0.0331(8) 0.0084(7) 0.0096(7) 0.0147(7) C12 0.0517(9) 0.0345(8) 0.0319(8) 0.0059(7) 0.0095(7) 0.0133(7) C13 0.0481(9) 0.0428(9) 0.0308(8) 0.0073(7) 0.0085(7) 0.0182(7) C14 0.0640(11) 0.0343(8) 0.0311(8) 0.0013(7) 0.0059(8) 0.0172(8) C15 0.0674(12) 0.0517(10) 0.0449(10) 0.0049(8) 0.0152(9) 0.0202(9) C16 0.0824(15) 0.0740(15) 0.0583(13) 0.0014(11) 0.0147(11) 0.0418(13) C17 0.116(2) 0.0618(14) 0.0575(14) -0.0009(11) 0.0091(13) 0.0548(15) C18 0.130(2) 0.0417(11) 0.0602(14) 0.0143(10) 0.0198(14) 0.0290(13) C19 0.0819(14) 0.0462(10) 0.0503(11) 0.0125(9) 0.0197(10) 0.0169(10) C20 0.0443(9) 0.0413(8) 0.0350(8) 0.0065(7) 0.0074(7) 0.0179(7) C21 0.0550(10) 0.0599(11) 0.0382(9) 0.0144(8) 0.0168(8) 0.0258(9) C22 0.0582(11) 0.0585(11) 0.0524(11) 0.0028(9) 0.0151(9) 0.0283(9) C23 0.0746(13) 0.0570(12) 0.0589(13) 0.0154(10) 0.0069(10) 0.0363(11) C24 0.0927(16) 0.0786(14) 0.0421(11) 0.0232(10) 0.0130(10) 0.0452(13) C25 0.0716(13) 0.0705(12) 0.0336(9) 0.0084(9) 0.0119(9) 0.0385(11) O3 0.0668(8) 0.0434(6) 0.0364(6) 0.0045(5) 0.0259(6) 0.0079(6) O4 0.0654(8) 0.0441(7) 0.0364(6) -0.0007(5) 0.0220(6) 0.0065(6) N7 0.0643(10) 0.0463(8) 0.0440(8) 0.0107(7) 0.0155(7) 0.0082(7) N8 0.0562(9) 0.0559(9) 0.0472(9) 0.0202(7) 0.0236(7) 0.0156(7) N9 0.0526(8) 0.0447(8) 0.0328(7) 0.0099(6) 0.0170(6) 0.0084(6) N10 0.0537(8) 0.0417(7) 0.0325(7) 0.0074(6) 0.0183(6) 0.0108(6) N11 0.0565(8) 0.0439(8) 0.0338(7) 0.0092(6) 0.0196(6) 0.0129(7) N12 0.0526(8) 0.0421(7) 0.0323(7) 0.0047(6) 0.0173(6) 0.0104(6) C26 0.0728(13) 0.0467(10) 0.0568(12) 0.0066(9) 0.0207(10) 0.0058(9) C27 0.0644(12) 0.0596(12) 0.0500(12) -0.0077(10) 0.0171(10) -0.0036(10) C28 0.0674(13) 0.0768(15) 0.0405(11) 0.0059(10) 0.0037(9) 0.0093(11) C29 0.0591(11) 0.0613(12) 0.0405(10) 0.0111(9) 0.0091(8) 0.0144(9) C30 0.0449(9) 0.0475(9) 0.0353(9) 0.0089(7) 0.0149(7) 0.0063(7) C31 0.0656(12) 0.0618(12) 0.0611(12) 0.0282(10) 0.0356(10) 0.0222(10) C32 0.0895(16) 0.0728(14) 0.0505(12) 0.0277(10) 0.0406(11) 0.0290(12) C33 0.0812(15) 0.0777(14) 0.0366(10) 0.0211(10) 0.0204(10) 0.0200(12) C34 0.0608(11) 0.0631(12) 0.0393(10) 0.0183(9) 0.0166(8) 0.0168(9) C35 0.0550(10) 0.0430(9) 0.0344(8) 0.0129(7) 0.0184(7) 0.0146(8) C36 0.0493(9) 0.0419(9) 0.0316(8) 0.0095(7) 0.0142(7) 0.0138(7) C37 0.0493(9) 0.0448(9) 0.0297(8) 0.0088(7) 0.0164(7) 0.0148(7) C38 0.0541(10) 0.0412(9) 0.0292(8) 0.0049(7) 0.0156(7) 0.0140(7) C39 0.0508(9) 0.0433(9) 0.0370(9) 0.0066(7) 0.0226(7) 0.0151(7) C40 0.0524(10) 0.0513(10) 0.0377(9) 0.0078(8) 0.0190(8) 0.0159(8) C41 0.0689(12) 0.0582(11) 0.0487(11) 0.0208(9) 0.0278(10) 0.0254(10) C42 0.0655(13) 0.0557(11) 0.0654(13) 0.0149(10) 0.0358(11) 0.0113(10) C43 0.0476(11) 0.0797(14) 0.0585(13) 0.0089(11) 0.0216(9) 0.0077(10) C44 0.0502(10) 0.0743(13) 0.0420(10) 0.0163(9) 0.0169(8) 0.0191(9) C45 0.0605(11) 0.0444(9) 0.0304(8) 0.0007(7) 0.0156(8) 0.0076(8) C46 0.0741(13) 0.0502(11) 0.0537(12) 0.0093(9) 0.0207(10) 0.0174(10) C47 0.0927(17) 0.0452(11) 0.0682(14) 0.0093(10) 0.0285(12) 0.0085(11) C48 0.0726(15) 0.0585(13) 0.0684(14) -0.0033(11) 0.0304(12) -0.0022(11) C49 0.0608(13) 0.0689(14) 0.0672(14) -0.0037(11) 0.0177(11) 0.0111(11) C50 0.0668(13) 0.0512(11) 0.0472(11) 0.0020(8) 0.0140(9) 0.0142(9) _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 O1 C12 1.3463(19) . ? O1 C14 1.407(2) . ? O2 C13 1.3462(19) . ? O2 C20 1.3973(19) . ? N1 C5 1.322(2) . ? N1 C1 1.337(2) . ? N2 C10 1.318(2) . ? N2 C6 1.343(3) . ? N3 C11 1.357(2) . ? N3 C5 1.4299(19) . ? N3 C10 1.444(2) . ? N4 C12 1.314(2) . ? N4 C11 1.341(2) . ? N5 C13 1.314(2) . ? N5 C11 1.344(2) . ? N6 C13 1.318(2) . ? N6 C12 1.327(2) . ? C1 C2 1.363(3) . ? C1 H1A 0.9400 . ? C2 C3 1.369(3) . ? C2 H2A 0.9400 . ? C3 C4 1.377(2) . ? C3 H3A 0.9400 . ? C4 C5 1.381(2) . ? C4 H4A 0.9400 . ? C6 C7 1.372(4) . ? C6 H6A 0.9400 . ? C7 C8 1.368(4) . ? C7 H7A 0.9400 . ? C8 C9 1.367(3) . ? C8 H8A 0.9400 . ? C9 C10 1.374(3) . ? C9 H9A 0.9400 . ? C14 C15 1.368(3) . ? C14 C19 1.369(3) . ? C15 C16 1.374(3) . ? C15 H15A 0.9400 . ? C16 C17 1.369(4) . ? C16 H16A 0.9400 . ? C17 C18 1.377(4) . ? C17 H17A 0.9400 . ? C18 C19 1.384(3) . ? C18 H18A 0.9400 . ? C19 H19A 0.9400 . ? C20 C25 1.368(2) . ? C20 C21 1.373(2) . ? C21 C22 1.375(3) . ? C21 H21A 0.9400 . ? C22 C23 1.366(3) . ? C22 H22A 0.9400 . ? C23 C24 1.361(3) . ? C23 H23A 0.9400 . ? C24 C25 1.376(3) . ? C24 H24A 0.9400 . ? C25 H25A 0.9400 . ? O3 C37 1.3542(19) . ? O3 C39 1.409(2) . ? O4 C38 1.3425(19) . ? O4 C45 1.407(2) . ? N7 C30 1.322(2) . ? N7 C26 1.345(2) . ? N8 C35 1.318(2) . ? N8 C31 1.334(2) . ? N9 C36 1.366(2) . ? N9 C35 1.432(2) . ? N9 C30 1.435(2) . ? N10 C37 1.317(2) . ? N10 C36 1.346(2) . ? N11 C38 1.314(2) . ? N11 C36 1.333(2) . ? N12 C37 1.320(2) . ? N12 C38 1.327(2) . ? C26 C27 1.365(3) . ? C26 H26A 0.9400 . ? C27 C28 1.376(3) . ? C27 H27A 0.9400 . ? C28 C29 1.366(3) . ? C28 H28A 0.9400 . ? C29 C30 1.372(2) . ? C29 H29A 0.9400 . ? C31 C32 1.370(3) . ? C31 H31A 0.9400 . ? C32 C33 1.368(3) . ? C32 H32A 0.9400 . ? C33 C34 1.371(3) . ? C33 H33A 0.9400 . ? C34 C35 1.378(2) . ? C34 H34A 0.9400 . ? C39 C40 1.370(2) . ? C39 C44 1.372(2) . ? C40 C41 1.381(3) . ? C40 H40A 0.9400 . ? C41 C42 1.365(3) . ? C41 H41A 0.9400 . ? C42 C43 1.379(3) . ? C42 H42A 0.9400 . ? C43 C44 1.382(3) . ? C43 H43A 0.9400 . ? C44 H44A 0.9400 . ? C45 C46 1.363(3) . ? C45 C50 1.372(3) . ? C46 C47 1.388(3) . ? C46 H46A 0.9400 . ? C47 C48 1.365(4) . ? C47 H47A 0.9400 . ? C48 C49 1.372(3) . ? C48 H48A 0.9400 . ? C49 C50 1.379(3) . ? C49 H49A 0.9400 . ? C50 H50A 0.9400 . ? 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 C12 O1 C14 116.23(12) . . ? C13 O2 C20 123.15(13) . . ? C5 N1 C1 116.83(17) . . ? C10 N2 C6 115.76(19) . . ? C11 N3 C5 124.97(13) . . ? C11 N3 C10 119.56(13) . . ? C5 N3 C10 115.36(13) . . ? C12 N4 C11 112.68(13) . . ? C13 N5 C11 113.03(14) . . ? C13 N6 C12 112.20(14) . . ? N1 C1 C2 123.8(2) . . ? N1 C1 H1A 118.1 . . ? C2 C1 H1A 118.1 . . ? C1 C2 C3 118.39(18) . . ? C1 C2 H2A 120.8 . . ? C3 C2 H2A 120.8 . . ? C2 C3 C4 119.48(19) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C3 C4 C5 117.65(18) . . ? C3 C4 H4A 121.2 . . ? C5 C4 H4A 121.2 . . ? N1 C5 C4 123.85(15) . . ? N1 C5 N3 112.96(15) . . ? C4 C5 N3 123.11(16) . . ? N2 C6 C7 123.3(2) . . ? N2 C6 H6A 118.3 . . ? C7 C6 H6A 118.3 . . ? C8 C7 C6 118.9(2) . . ? C8 C7 H7A 120.5 . . ? C6 C7 H7A 120.5 . . ? C9 C8 C7 119.1(2) . . ? C9 C8 H8A 120.5 . . ? C7 C8 H8A 120.5 . . ? C8 C9 C10 117.7(2) . . ? C8 C9 H9A 121.2 . . ? C10 C9 H9A 121.2 . . ? N2 C10 C9 125.22(16) . . ? N2 C10 N3 114.19(15) . . ? C9 C10 N3 120.57(16) . . ? N4 C11 N5 125.79(15) . . ? N4 C11 N3 118.48(14) . . ? N5 C11 N3 115.73(14) . . ? N4 C12 N6 128.22(15) . . ? N4 C12 O1 114.29(14) . . ? N6 C12 O1 117.48(14) . . ? N5 C13 N6 128.03(14) . . ? N5 C13 O2 112.68(14) . . ? N6 C13 O2 119.28(14) . . ? C15 C14 C19 122.82(18) . . ? C15 C14 O1 119.19(16) . . ? C19 C14 O1 117.99(18) . . ? C14 C15 C16 118.7(2) . . ? C14 C15 H15A 120.7 . . ? C16 C15 H15A 120.7 . . ? C17 C16 C15 120.1(2) . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? C16 C17 C18 120.1(2) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? C17 C18 C19 120.7(2) . . ? C17 C18 H18A 119.6 . . ? C19 C18 H18A 119.6 . . ? C14 C19 C18 117.4(2) . . ? C14 C19 H19A 121.3 . . ? C18 C19 H19A 121.3 . . ? C25 C20 C21 121.13(16) . . ? C25 C20 O2 114.32(15) . . ? C21 C20 O2 124.37(15) . . ? C20 C21 C22 118.73(17) . . ? C20 C21 H21A 120.6 . . ? C22 C21 H21A 120.6 . . ? C23 C22 C21 120.50(19) . . ? C23 C22 H22A 119.7 . . ? C21 C22 H22A 119.7 . . ? C24 C23 C22 120.19(18) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C23 C24 C25 120.31(18) . . ? C23 C24 H24A 119.8 . . ? C25 C24 H24A 119.8 . . ? C20 C25 C24 119.13(18) . . ? C20 C25 H25A 120.4 . . ? C24 C25 H25A 120.4 . . ? C37 O3 C39 119.43(13) . . ? C38 O4 C45 117.03(13) . . ? C30 N7 C26 116.50(16) . . ? C35 N8 C31 116.85(16) . . ? C36 N9 C35 122.10(14) . . ? C36 N9 C30 120.57(13) . . ? C35 N9 C30 117.21(13) . . ? C37 N10 C36 112.55(14) . . ? C38 N11 C36 113.07(14) . . ? C37 N12 C38 111.92(14) . . ? N7 C26 C27 123.2(2) . . ? N7 C26 H26A 118.4 . . ? C27 C26 H26A 118.4 . . ? C26 C27 C28 118.66(19) . . ? C26 C27 H27A 120.7 . . ? C28 C27 H27A 120.7 . . ? C29 C28 C27 119.25(19) . . ? C29 C28 H28A 120.4 . . ? C27 C28 H28A 120.4 . . ? C28 C29 C30 117.96(19) . . ? C28 C29 H29A 121.0 . . ? C30 C29 H29A 121.0 . . ? N7 C30 C29 124.36(17) . . ? N7 C30 N9 114.49(14) . . ? C29 C30 N9 121.15(16) . . ? N8 C31 C32 123.9(2) . . ? N8 C31 H31A 118.1 . . ? C32 C31 H31A 118.1 . . ? C33 C32 C31 118.00(18) . . ? C33 C32 H32A 121.0 . . ? C31 C32 H32A 121.0 . . ? C32 C33 C34 119.48(19) . . ? C32 C33 H33A 120.3 . . ? C34 C33 H33A 120.3 . . ? C33 C34 C35 118.02(19) . . ? C33 C34 H34A 121.0 . . ? C35 C34 H34A 121.0 . . ? N8 C35 C34 123.76(16) . . ? N8 C35 N9 114.49(14) . . ? C34 C35 N9 121.72(16) . . ? N11 C36 N10 125.93(15) . . ? N11 C36 N9 117.25(14) . . ? N10 C36 N9 116.81(14) . . ? N10 C37 N12 128.39(15) . . ? N10 C37 O3 113.38(14) . . ? N12 C37 O3 118.22(14) . . ? N11 C38 N12 128.09(15) . . ? N11 C38 O4 114.31(14) . . ? N12 C38 O4 117.60(14) . . ? C40 C39 C44 121.87(16) . . ? C40 C39 O3 115.93(15) . . ? C44 C39 O3 122.07(16) . . ? C39 C40 C41 118.82(17) . . ? C39 C40 H40A 120.6 . . ? C41 C40 H40A 120.6 . . ? C42 C41 C40 120.41(18) . . ? C42 C41 H41A 119.8 . . ? C40 C41 H41A 119.8 . . ? C41 C42 C43 120.03(18) . . ? C41 C42 H42A 120.0 . . ? C43 C42 H42A 120.0 . . ? C42 C43 C44 120.36(19) . . ? C42 C43 H43A 119.8 . . ? C44 C43 H43A 119.8 . . ? C39 C44 C43 118.47(18) . . ? C39 C44 H44A 120.8 . . ? C43 C44 H44A 120.8 . . ? C46 C45 C50 122.37(19) . . ? C46 C45 O4 118.06(18) . . ? C50 C45 O4 119.51(16) . . ? C45 C46 C47 117.9(2) . . ? C45 C46 H46A 121.1 . . ? C47 C46 H46A 121.1 . . ? C48 C47 C46 120.8(2) . . ? C48 C47 H47A 119.6 . . ? C46 C47 H47A 119.6 . . ? C47 C48 C49 120.3(2) . . ? C47 C48 H48A 119.9 . . ? C49 C48 H48A 119.9 . . ? C48 C49 C50 119.9(2) . . ? C48 C49 H49A 120.0 . . ? C50 C49 H49A 120.0 . . ? C45 C50 C49 118.8(2) . . ? C45 C50 H50A 120.6 . . ? C49 C50 H50A 120.6 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.97 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.207 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.043