# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 # Attachment '- data_790319.cif' data_publication_text #TrackingRef '- data_790319.cif' _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author_name 'Mario Ruben' _publ_contact_author_address ;KIT - Karlsruher Institut f\"ur Technologie Institut f\"ur Nanotechnologie Hermann-von-Helmholtz-Platz 1 Geb. 640 Eggenstein-Leopoldshafen, D-76344 ; _publ_contact_author_email mario.ruben@int.fzk.de _publ_contact_author_phone +49(0721)60826781 loop_ _publ_author_name 'Rodrigo Gonzalez-Prieto' 'Benoit Fleury' 'Frank Schramm' 'Giorgio Zoppellaro' ; R.Chandrasekar ; 'Olaf Fuhr' 'Sergei Lebedkin' 'Manfred Kappes' 'Mario Ruben ' data_790319 _database_code_depnum_ccdc_archive 'CCDC 790319' #TrackingRef '- data_790319.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H34 Cl2 Fe N10 O8' _chemical_formula_weight 1077.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.180(3) _cell_length_b 8.3692(17) _cell_length_c 36.505(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.69(3) _cell_angle_gamma 90.00 _cell_volume 4557.2(16) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2208 _exptl_absorpt_coefficient_mu 0.522 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9123 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm, multiple pinhole' _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_source_power 2.00 _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector 'image plate ( 34 cm diameter )' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6333 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 23.64 _reflns_number_total 3259 _reflns_number_gt 2169 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0806P)^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 0.0034(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3259 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1348 _refine_ls_wR_factor_gt 0.1215 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.0000 0.41926(10) 0.2500 0.0465(3) Uani 1 2 d S . . N1 N -0.0493(2) 0.5938(4) 0.28433(11) 0.0524(9) Uani 1 1 d . . . N2 N -0.0373(2) 0.5545(4) 0.32136(11) 0.0506(9) Uani 1 1 d . . . N3 N 0.0483(2) 0.3525(4) 0.30647(10) 0.0479(9) Uani 1 1 d . . . N4 N 0.1364(2) 0.1691(4) 0.28432(11) 0.0486(9) Uani 1 1 d . . . N5 N 0.1092(2) 0.2449(4) 0.25104(11) 0.0505(9) Uani 1 1 d . . . C1 C -0.0863(3) 0.7384(5) 0.28190(15) 0.0573(12) Uani 1 1 d . . . H1 H -0.1025 0.7974 0.2594 0.069 Uiso 1 1 calc R . . C2 C -0.0981(3) 0.7923(6) 0.31719(15) 0.0609(12) Uani 1 1 d . . . H2 H -0.1238 0.8908 0.3227 0.073 Uiso 1 1 calc R . . C3 C -0.0655(3) 0.6750(5) 0.34177(14) 0.0561(12) Uani 1 1 d . . . H3 H -0.0627 0.6765 0.3680 0.067 Uiso 1 1 calc R . . C4 C 0.0121(3) 0.4160(5) 0.33364(13) 0.0494(10) Uani 1 1 d . . . C5 C 0.0210(3) 0.3529(5) 0.36898(13) 0.0526(11) Uani 1 1 d . . . H5 H -0.0072 0.4019 0.3873 0.063 Uiso 1 1 calc R . . C6 C 0.0725(3) 0.2154(6) 0.37717(13) 0.0533(11) Uani 1 1 d . . . C7 C 0.1127(3) 0.1472(5) 0.34939(13) 0.0531(11) Uani 1 1 d . . . H7 H 0.1484 0.0535 0.3540 0.064 Uiso 1 1 calc R . . C8 C 0.0986(3) 0.2210(5) 0.31495(13) 0.0484(10) Uani 1 1 d . . . C9 C 0.2013(3) 0.0589(5) 0.28258(14) 0.0525(11) Uani 1 1 d . . . H9 H 0.2302 -0.0080 0.3022 0.063 Uiso 1 1 calc R . . C10 C 0.2166(3) 0.0640(5) 0.24670(14) 0.0546(11) Uani 1 1 d . . . H10 H 0.2587 0.0019 0.2366 0.066 Uiso 1 1 calc R . . C11 C 0.1579(3) 0.1789(5) 0.22793(14) 0.0522(11) Uani 1 1 d . . . H11 H 0.1533 0.2062 0.2024 0.063 Uiso 1 1 calc R . . C12 C 0.0843(3) 0.1368(6) 0.41408(14) 0.0570(12) Uani 1 1 d . . . C13 C 0.0719(3) -0.0285(6) 0.41457(14) 0.0606(12) Uani 1 1 d . . . H13 H 0.0581 -0.0857 0.3917 0.073 Uiso 1 1 calc R . . C14 C 0.0796(3) -0.1099(6) 0.44813(16) 0.0653(13) Uani 1 1 d . . . H14 H 0.0703 -0.2222 0.4479 0.078 Uiso 1 1 calc R . . C15 C 0.1008(3) -0.0301(6) 0.48210(14) 0.0597(12) Uani 1 1 d . . . C16 C 0.1088(3) -0.1122(7) 0.51728(16) 0.0697(14) Uani 1 1 d . . . H16 H 0.0984 -0.2241 0.5174 0.084 Uiso 1 1 calc R . . C17 C 0.1307(3) -0.0348(7) 0.54974(16) 0.0696(14) Uani 1 1 d . . . H17 H 0.1354 -0.0929 0.5724 0.084 Uiso 1 1 calc R . . C18 C 0.1471(3) 0.1339(6) 0.55109(15) 0.0639(13) Uani 1 1 d . . . C19 C 0.1710(3) 0.2171(7) 0.58472(15) 0.0682(14) Uani 1 1 d . . . H19 H 0.1774 0.1610 0.6077 0.082 Uiso 1 1 calc R . . C20 C 0.1855(3) 0.3813(7) 0.58490(15) 0.0680(14) Uani 1 1 d . . . H20 H 0.1995 0.4365 0.6080 0.082 Uiso 1 1 calc R . . C21 C 0.1799(3) 0.4645(7) 0.55209(16) 0.0686(14) Uani 1 1 d . . . H21 H 0.1915 0.5761 0.5528 0.082 Uiso 1 1 calc R . . C22 C 0.1571(3) 0.3866(6) 0.51731(14) 0.0594(12) Uani 1 1 d . . . C23 C 0.1547(3) 0.4654(6) 0.48267(15) 0.0599(12) Uani 1 1 d . . . H23 H 0.1704 0.5753 0.4827 0.072 Uiso 1 1 calc R . . C24 C 0.1309(3) 0.3897(6) 0.44974(15) 0.0601(12) Uani 1 1 d . . . H24 H 0.1292 0.4481 0.4273 0.072 Uiso 1 1 calc R . . C25 C 0.1080(3) 0.2225(6) 0.44763(14) 0.0580(12) Uani 1 1 d . . . C26 C 0.1159(3) 0.1373(6) 0.48237(14) 0.0555(11) Uani 1 1 d . . . C27 C 0.1395(3) 0.2195(6) 0.51677(14) 0.0590(12) Uani 1 1 d . . . Cl1 Cl 0.20770(7) 0.68114(14) 0.34677(4) 0.0593(3) Uani 1 1 d . . . O1 O 0.2471(3) 0.5327(4) 0.33933(12) 0.0834(12) Uani 1 1 d . . . O2 O 0.2755(2) 0.8038(5) 0.35288(12) 0.0823(11) Uani 1 1 d . . . O3 O 0.1664(3) 0.6644(5) 0.37852(13) 0.0930(13) Uani 1 1 d . . . O4 O 0.1420(2) 0.7255(5) 0.31509(13) 0.0882(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0515(5) 0.0467(5) 0.0412(6) 0.000 0.0083(4) 0.000 N1 0.0551(19) 0.053(2) 0.048(2) 0.0088(19) 0.0072(16) 0.0037(17) N2 0.0569(19) 0.050(2) 0.046(2) 0.0025(18) 0.0120(16) 0.0060(16) N3 0.0545(18) 0.0439(19) 0.046(2) -0.0074(17) 0.0112(16) 0.0005(16) N4 0.0537(18) 0.047(2) 0.045(2) 0.0012(18) 0.0108(16) 0.0007(16) N5 0.0596(19) 0.053(2) 0.040(2) 0.0042(17) 0.0103(17) -0.0011(16) C1 0.066(3) 0.049(3) 0.056(3) 0.002(2) 0.009(2) 0.007(2) C2 0.073(3) 0.055(3) 0.055(3) -0.001(3) 0.013(2) 0.013(2) C3 0.066(3) 0.057(3) 0.048(3) -0.007(2) 0.017(2) 0.008(2) C4 0.055(2) 0.044(2) 0.049(3) -0.001(2) 0.0079(19) 0.0034(19) C5 0.066(3) 0.054(3) 0.039(3) 0.001(2) 0.012(2) 0.007(2) C6 0.065(3) 0.055(3) 0.040(3) 0.000(2) 0.010(2) 0.003(2) C7 0.062(2) 0.052(3) 0.044(3) 0.001(2) 0.008(2) 0.007(2) C8 0.052(2) 0.050(2) 0.043(3) -0.003(2) 0.0100(19) -0.0004(19) C9 0.055(2) 0.048(2) 0.054(3) 0.000(2) 0.010(2) 0.0055(19) C10 0.057(2) 0.050(3) 0.059(3) -0.004(2) 0.013(2) 0.001(2) C11 0.058(2) 0.055(3) 0.047(3) -0.002(2) 0.018(2) 0.002(2) C12 0.071(3) 0.054(3) 0.046(3) 0.004(2) 0.013(2) 0.010(2) C13 0.076(3) 0.060(3) 0.045(3) 0.001(2) 0.011(2) 0.010(2) C14 0.083(3) 0.051(3) 0.063(4) 0.003(3) 0.019(3) 0.008(2) C15 0.075(3) 0.058(3) 0.048(3) 0.008(2) 0.016(2) 0.008(2) C16 0.086(3) 0.065(3) 0.063(4) 0.015(3) 0.028(3) 0.019(3) C17 0.083(3) 0.072(4) 0.058(4) 0.011(3) 0.023(3) 0.016(3) C18 0.072(3) 0.071(3) 0.052(3) 0.004(3) 0.018(2) 0.020(2) C19 0.074(3) 0.085(4) 0.046(3) 0.000(3) 0.012(2) 0.017(3) C20 0.078(3) 0.082(4) 0.045(3) -0.007(3) 0.012(2) 0.012(3) C21 0.071(3) 0.073(3) 0.060(4) -0.004(3) 0.008(2) 0.009(2) C22 0.067(3) 0.060(3) 0.052(3) -0.004(2) 0.012(2) 0.012(2) C23 0.074(3) 0.053(3) 0.052(3) 0.002(2) 0.011(2) 0.007(2) C24 0.076(3) 0.055(3) 0.051(3) 0.003(2) 0.014(2) 0.010(2) C25 0.070(3) 0.059(3) 0.047(3) 0.002(2) 0.014(2) 0.015(2) C26 0.067(3) 0.055(3) 0.046(3) 0.005(2) 0.013(2) 0.010(2) C27 0.065(3) 0.065(3) 0.048(3) 0.007(3) 0.013(2) 0.016(2) Cl1 0.0679(6) 0.0549(7) 0.0578(8) 0.0022(6) 0.0188(6) 0.0047(5) O1 0.109(3) 0.059(2) 0.091(3) 0.004(2) 0.042(2) 0.0270(19) O2 0.088(2) 0.078(3) 0.077(3) -0.004(2) 0.0057(19) -0.026(2) O3 0.122(3) 0.090(3) 0.084(3) 0.010(2) 0.065(3) 0.009(2) O4 0.074(2) 0.089(3) 0.092(3) 0.033(2) -0.006(2) -0.0064(19) _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 N3 2.130(4) 2 ? Fe1 N3 2.130(4) . ? Fe1 N1 2.148(4) . ? Fe1 N1 2.148(4) 2 ? Fe1 N5 2.203(4) . ? Fe1 N5 2.203(4) 2 ? N1 C1 1.330(6) . ? N1 N2 1.370(5) . ? N2 C3 1.369(6) . ? N2 C4 1.408(5) . ? N3 C4 1.331(5) . ? N3 C8 1.342(5) . ? N4 C9 1.360(5) . ? N4 N5 1.365(5) . ? N4 C8 1.416(6) . ? N5 C11 1.340(5) . ? C1 C2 1.407(7) . ? C2 C3 1.360(7) . ? C4 C5 1.377(6) . ? C5 C6 1.392(6) . ? C6 C7 1.398(6) . ? C6 C12 1.480(7) . ? C7 C8 1.381(6) . ? C9 C10 1.373(7) . ? C10 C11 1.400(6) . ? C12 C13 1.397(7) . ? C12 C25 1.407(7) . ? C13 C14 1.387(7) . ? C14 C15 1.393(7) . ? C15 C26 1.420(7) . ? C15 C16 1.441(7) . ? C16 C17 1.337(8) . ? C17 C18 1.433(7) . ? C18 C19 1.400(7) . ? C18 C27 1.429(7) . ? C19 C20 1.391(7) . ? C20 C21 1.374(7) . ? C21 C22 1.412(7) . ? C22 C23 1.421(7) . ? C22 C27 1.424(7) . ? C23 C24 1.348(7) . ? C24 C25 1.441(7) . ? C25 C26 1.440(7) . ? C26 C27 1.418(7) . ? Cl1 O3 1.423(4) . ? Cl1 O1 1.427(3) . ? Cl1 O4 1.429(4) . ? Cl1 O2 1.441(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Fe1 N3 149.58(19) 2 . ? N3 Fe1 N1 130.42(13) 2 . ? N3 Fe1 N1 73.05(13) . . ? N3 Fe1 N1 73.05(13) 2 2 ? N3 Fe1 N1 130.42(13) . 2 ? N1 Fe1 N1 94.3(2) . 2 ? N3 Fe1 N5 88.02(14) 2 . ? N3 Fe1 N5 71.76(13) . . ? N1 Fe1 N5 141.54(14) . . ? N1 Fe1 N5 96.79(13) 2 . ? N3 Fe1 N5 71.75(13) 2 2 ? N3 Fe1 N5 88.03(14) . 2 ? N1 Fe1 N5 96.79(13) . 2 ? N1 Fe1 N5 141.54(14) 2 2 ? N5 Fe1 N5 97.02(18) . 2 ? C1 N1 N2 105.2(4) . . ? C1 N1 Fe1 140.2(3) . . ? N2 N1 Fe1 114.5(3) . . ? C3 N2 N1 111.2(4) . . ? C3 N2 C4 129.4(4) . . ? N1 N2 C4 118.5(3) . . ? C4 N3 C8 116.8(4) . . ? C4 N3 Fe1 120.1(3) . . ? C8 N3 Fe1 121.1(3) . . ? C9 N4 N5 112.1(3) . . ? C9 N4 C8 130.4(4) . . ? N5 N4 C8 117.4(3) . . ? C11 N5 N4 104.9(3) . . ? C11 N5 Fe1 139.8(3) . . ? N4 N5 Fe1 115.2(2) . . ? N1 C1 C2 110.7(4) . . ? C3 C2 C1 106.3(4) . . ? C2 C3 N2 106.6(4) . . ? N3 C4 C5 124.2(4) . . ? N3 C4 N2 111.1(4) . . ? C5 C4 N2 124.6(4) . . ? C4 C5 C6 118.2(4) . . ? C5 C6 C7 119.0(4) . . ? C5 C6 C12 122.1(4) . . ? C7 C6 C12 118.9(4) . . ? C8 C7 C6 117.5(4) . . ? N3 C8 C7 124.2(4) . . ? N3 C8 N4 111.4(4) . . ? C7 C8 N4 124.3(4) . . ? N4 C9 C10 106.0(4) . . ? C9 C10 C11 106.5(4) . . ? N5 C11 C10 110.5(4) . . ? C13 C12 C25 120.4(5) . . ? C13 C12 C6 117.3(4) . . ? C25 C12 C6 122.3(4) . . ? C14 C13 C12 120.6(5) . . ? C13 C14 C15 121.2(5) . . ? C14 C15 C26 119.3(4) . . ? C14 C15 C16 122.2(5) . . ? C26 C15 C16 118.5(5) . . ? C17 C16 C15 121.7(5) . . ? C16 C17 C18 121.4(5) . . ? C19 C18 C27 119.0(5) . . ? C19 C18 C17 122.4(5) . . ? C27 C18 C17 118.6(5) . . ? C20 C19 C18 120.7(5) . . ? C21 C20 C19 120.8(5) . . ? C20 C21 C22 121.0(5) . . ? C21 C22 C23 123.2(5) . . ? C21 C22 C27 118.7(5) . . ? C23 C22 C27 118.0(5) . . ? C24 C23 C22 122.3(5) . . ? C23 C24 C25 121.8(5) . . ? C12 C25 C26 118.7(4) . . ? C12 C25 C24 124.1(4) . . ? C26 C25 C24 117.0(5) . . ? C27 C26 C15 119.9(4) . . ? C27 C26 C25 120.4(4) . . ? C15 C26 C25 119.7(5) . . ? C26 C27 C22 120.3(4) . . ? C26 C27 C18 120.0(5) . . ? C22 C27 C18 119.7(5) . . ? O3 Cl1 O1 109.4(2) . . ? O3 Cl1 O4 109.7(3) . . ? O1 Cl1 O4 109.1(3) . . ? O3 Cl1 O2 110.7(3) . . ? O1 Cl1 O2 109.7(2) . . ? O4 Cl1 O2 108.1(2) . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 23.64 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.309 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.070