# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_compd _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H38 Fe2 N8 O18' _chemical_formula_weight 814.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0040 0.0020 '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 0.0070 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3650 0.9380 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5580(17) _cell_length_b 18.487(4) _cell_length_c 11.217(2) _cell_angle_alpha 90 _cell_angle_beta 108.06(3) _cell_angle_gamma 90 _cell_volume 1687.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 96(2) _cell_measurement_reflns_used 29105 _cell_measurement_theta_min 0.43 _cell_measurement_theta_max 30.00 _exptl_crystal_description plate _exptl_crystal_colour 'greenish yellow' _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.603 _exptl_crystal_F_000 844 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.080 _exptl_absorpt_coefficient_mu 1.091 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.780 _exptl_absorpt_correction_T_max 0.918 _exptl_absorpt_process_details 'HKL3000 Scalepack' _exptl_special_details ; ? ; _diffrn_ambient_temperature 96(2) _diffrn_radiation_wavelength 0.750 _diffrn_radiation_type synchrotron _diffrn_source 'PLSII 2D bending magnet' _diffrn_measurement_device_type 'ADSC Q210 CCD area detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14596 _diffrn_reflns_av_unetI/netI 0.0238 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.325 _diffrn_reflns_theta_max 29.834 _diffrn_reflns_theta_full 26.744 _diffrn_measured_fraction_theta_max 0.951 _diffrn_measured_fraction_theta_full 0.960 _diffrn_reflns_Laue_measured_fraction_max 0.951 _diffrn_reflns_Laue_measured_fraction_full 0.960 _diffrn_reflns_point_group_measured_fraction_max 0.951 _diffrn_reflns_point_group_measured_fraction_full 0.960 _reflns_number_total 3919 _reflns_number_gt 3524 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'PAL ADSC Quantum-210 ADX Program' _computing_cell_refinement HKL3000 _computing_data_reduction HKL3000 _computing_structure_solution 'SHELXS-2013 (sheldrick, 2013)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material WINGX _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1281P)^2^+2.2883P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.052(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3919 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.1935 _refine_ls_wR_factor_gt 0.1885 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.98008(5) 0.08573(2) 0.01334(4) 0.0223(2) Uani 1 1 d . . . . . N1 N 0.9715(3) 0.11514(14) -0.1676(3) 0.0279(6) Uani 1 1 d . . . . . N2 N 1.2127(3) 0.14811(13) 0.0474(2) 0.0247(5) Uani 1 1 d . . . . . N3 N 0.7463(3) 0.19427(14) -0.0205(3) 0.0282(6) Uani 1 1 d . . . . . N4 N 0.7258(4) 0.12401(16) 0.2972(3) 0.0318(6) Uani 1 1 d . . . . . O1 O 1.0394(3) 0.10519(13) 0.1975(2) 0.0293(5) Uani 1 1 d . . . . . H1 H 0.9646 0.1220 0.2233 0.044 Uiso 1 1 calc R U . . . O2 O 1.1378(3) 0.00725(11) 0.0067(2) 0.0248(4) Uani 1 1 d . . . . . O3 O 0.7453(3) 0.12457(12) -0.0167(2) 0.0298(5) Uani 1 1 d . . . . . O4 O 0.6168(3) 0.22751(13) -0.0410(3) 0.0364(6) Uani 1 1 d . . . . . O5 O 0.8813(3) 0.22452(13) -0.0019(3) 0.0364(6) Uani 1 1 d . . . . . O6 O 0.8217(4) 0.16913(15) 0.2740(3) 0.0420(6) Uani 1 1 d . . . . . O7 O 0.6106(3) 0.14387(15) 0.3338(3) 0.0398(6) Uani 1 1 d . . . . . O8 O 0.7460(5) 0.05718(16) 0.2834(3) 0.0564(8) Uani 1 1 d . . . . . C1 C 0.8681(5) 0.08290(18) -0.2680(3) 0.0332(7) Uani 1 1 d . . . . . H1A H 0.7875 0.0505 -0.2570 0.040 Uiso 1 1 calc R U . . . C2 C 0.8761(6) 0.0958(2) -0.3879(4) 0.0424(9) Uani 1 1 d . . . . . H2 H 0.8028 0.0723 -0.4586 0.051 Uiso 1 1 calc R U . . . C3 C 0.9934(5) 0.1439(2) -0.4023(3) 0.0436(9) Uani 1 1 d . . . . . H3 H 1.0001 0.1543 -0.4835 0.052 Uiso 1 1 calc R U . . . C4 C 1.1011(5) 0.1769(2) -0.2975(3) 0.0361(7) Uani 1 1 d . . . . . H4 H 1.1825 0.2096 -0.3060 0.043 Uiso 1 1 calc R U . . . C5 C 1.0878(4) 0.16115(17) -0.1810(3) 0.0287(6) Uani 1 1 d . . . . . C6 C 1.1957(4) 0.19552(17) -0.0622(3) 0.0302(6) Uani 1 1 d . . . . . H6A H 1.3057 0.2051 -0.0705 0.036 Uiso 1 1 calc R U . . . H6B H 1.1476 0.2424 -0.0490 0.036 Uiso 1 1 calc R U . . . C7 C 1.2354(4) 0.19015(17) 0.1647(3) 0.0305(7) Uani 1 1 d . . . . . H7A H 1.1632 0.2332 0.1471 0.037 Uiso 1 1 calc R U . . . H7B H 1.3508 0.2067 0.1985 0.037 Uiso 1 1 calc R U . . . C8 C 1.1924(4) 0.14168(19) 0.2599(3) 0.0324(7) Uani 1 1 d . . . . . H8A H 1.2809 0.1058 0.2939 0.039 Uiso 1 1 calc R U . . . H8B H 1.1808 0.1711 0.3304 0.039 Uiso 1 1 calc R U . . . C9 C 1.3488(4) 0.09479(16) 0.0640(3) 0.0278(6) Uani 1 1 d . . . . . H9A H 1.3924 0.0806 0.1533 0.033 Uiso 1 1 calc R U . . . H9B H 1.4392 0.1172 0.0393 0.033 Uiso 1 1 calc R U . . . C10 C 1.2870(4) 0.02842(16) -0.0155(3) 0.0256(6) Uani 1 1 d . . . . . H10A H 1.2663 0.0397 -0.1054 0.031 Uiso 1 1 calc R U . . . H10B H 1.3691 -0.0110 0.0084 0.031 Uiso 1 1 calc R U . . . C11 C 0.5604(10) -0.0867(4) 0.3803(8) 0.0837(19) Uiso 1 1 d . . . . . H11A H 0.6793 -0.0810 0.4190 0.126 Uiso 1 1 calc R U . . . H11B H 0.5391 -0.1156 0.3036 0.126 Uiso 1 1 calc R U . . . H11C H 0.5141 -0.1113 0.4391 0.126 Uiso 1 1 calc R U . . . O9 O 0.4887(7) -0.0197(3) 0.3512(6) 0.0961(15) Uiso 1 1 d . . . . . H9 H 0.4886 -0.0077 0.2789 0.144 Uiso 1 1 calc R U . . . 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 0.0247(3) 0.0184(3) 0.0237(3) -0.00029(13) 0.0074(2) -0.00116(13) N1 0.0315(14) 0.0265(12) 0.0254(12) 0.0033(9) 0.0084(11) -0.0011(10) N2 0.0254(13) 0.0202(11) 0.0264(12) -0.0004(9) 0.0050(10) -0.0012(9) N3 0.0302(14) 0.0232(12) 0.0325(13) 0.0017(10) 0.0115(11) 0.0008(9) N4 0.0367(16) 0.0334(14) 0.0241(12) -0.0032(10) 0.0075(12) 0.0058(11) O1 0.0297(12) 0.0318(11) 0.0263(11) -0.0038(9) 0.0087(9) -0.0028(9) O2 0.0227(11) 0.0201(9) 0.0330(11) 0.0000(8) 0.0108(9) -0.0023(7) O3 0.0314(12) 0.0198(10) 0.0393(12) 0.0020(8) 0.0124(10) 0.0036(8) O4 0.0337(13) 0.0264(11) 0.0518(15) 0.0068(10) 0.0174(12) 0.0093(9) O5 0.0327(13) 0.0315(12) 0.0453(14) -0.0022(10) 0.0126(11) -0.0060(9) O6 0.0470(16) 0.0410(14) 0.0401(14) -0.0057(11) 0.0164(13) -0.0035(11) O7 0.0328(14) 0.0465(15) 0.0398(13) -0.0143(11) 0.0109(11) -0.0012(10) O8 0.084(2) 0.0338(14) 0.0618(19) -0.0018(13) 0.0374(18) 0.0118(15) C1 0.0344(19) 0.0350(17) 0.0269(16) 0.0043(12) 0.0046(14) -0.0041(12) C2 0.052(2) 0.045(2) 0.0257(16) 0.0024(14) 0.0062(16) -0.0085(16) C3 0.055(2) 0.048(2) 0.0285(17) 0.0059(15) 0.0145(17) -0.0036(17) C4 0.043(2) 0.0332(16) 0.0354(17) 0.0074(13) 0.0161(15) -0.0012(13) C5 0.0310(16) 0.0259(14) 0.0297(15) 0.0039(11) 0.0102(13) -0.0007(11) C6 0.0309(16) 0.0238(13) 0.0349(16) 0.0054(11) 0.0089(13) -0.0036(11) C7 0.0322(17) 0.0238(14) 0.0329(16) -0.0055(11) 0.0062(13) -0.0023(11) C8 0.0328(17) 0.0344(16) 0.0271(15) -0.0077(12) 0.0050(13) -0.0029(12) C9 0.0259(16) 0.0220(13) 0.0348(16) -0.0009(11) 0.0086(13) -0.0003(10) C10 0.0215(14) 0.0218(13) 0.0350(15) -0.0014(11) 0.0107(12) -0.0031(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 O2 1.970(2) 3_755 ? Fe1 O2 1.999(2) . ? Fe1 O1 2.001(2) . ? Fe1 O3 2.061(2) . ? Fe1 N1 2.080(3) . ? Fe1 N2 2.229(3) . ? N1 C1 1.337(4) . ? N1 C5 1.353(4) . ? N2 C6 1.480(4) . ? N2 C7 1.488(4) . ? N2 C9 1.493(4) . ? N3 O4 1.226(4) . ? N3 O5 1.242(4) . ? N3 O3 1.289(3) . ? N4 O7 1.236(4) . ? N4 O6 1.252(4) . ? N4 O8 1.264(4) . ? O1 C8 1.446(4) . ? O1 H1 0.8400 . ? O2 C10 1.429(3) . ? O2 Fe1 1.970(2) 3_755 ? C1 C2 1.389(5) . ? C1 H1A 0.9500 . ? C2 C3 1.387(6) . ? C2 H2 0.9500 . ? C3 C4 1.389(6) . ? C3 H3 0.9500 . ? C4 C5 1.377(5) . ? C4 H4 0.9500 . ? C5 C6 1.506(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.524(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.513(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O9 1.376(9) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? O9 H9 0.8400 . ? 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 O2 Fe1 O2 71.95(10) 3_755 . ? O2 Fe1 O1 103.40(10) 3_755 . ? O2 Fe1 O1 102.17(10) . . ? O2 Fe1 O3 81.18(9) 3_755 . ? O2 Fe1 O3 151.92(9) . . ? O1 Fe1 O3 91.64(10) . . ? O2 Fe1 N1 104.76(10) 3_755 . ? O2 Fe1 N1 88.47(10) . . ? O1 Fe1 N1 151.77(11) . . ? O3 Fe1 N1 90.68(11) . . ? O2 Fe1 N2 150.39(9) 3_755 . ? O2 Fe1 N2 78.72(9) . . ? O1 Fe1 N2 78.61(10) . . ? O3 Fe1 N2 128.43(9) . . ? N1 Fe1 N2 77.97(11) . . ? C1 N1 C5 120.3(3) . . ? C1 N1 Fe1 121.3(2) . . ? C5 N1 Fe1 117.9(2) . . ? C6 N2 C7 112.2(2) . . ? C6 N2 C9 111.5(3) . . ? C7 N2 C9 110.6(3) . . ? C6 N2 Fe1 108.15(19) . . ? C7 N2 Fe1 106.66(19) . . ? C9 N2 Fe1 107.49(18) . . ? O4 N3 O5 123.1(3) . . ? O4 N3 O3 119.5(3) . . ? O5 N3 O3 117.4(3) . . ? O7 N4 O6 120.8(3) . . ? O7 N4 O8 119.0(3) . . ? O6 N4 O8 120.2(3) . . ? C8 O1 Fe1 119.07(19) . . ? C8 O1 H1 109.5 . . ? Fe1 O1 H1 116.5 . . ? C10 O2 Fe1 132.25(17) . 3_755 ? C10 O2 Fe1 117.25(16) . . ? Fe1 O2 Fe1 108.05(10) 3_755 . ? N3 O3 Fe1 109.70(19) . . ? N1 C1 C2 121.4(3) . . ? N1 C1 H1A 119.3 . . ? C2 C1 H1A 119.3 . . ? C3 C2 C1 118.5(4) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 118.8(3) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 121.2(3) . . ? N1 C5 C6 115.9(3) . . ? C4 C5 C6 122.8(3) . . ? N2 C6 C5 111.1(2) . . ? N2 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N2 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N2 C7 C8 108.6(2) . . ? N2 C7 H7A 110.0 . . ? C8 C7 H7A 110.0 . . ? N2 C7 H7B 110.0 . . ? C8 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? O1 C8 C7 108.3(3) . . ? O1 C8 H8A 110.0 . . ? C7 C8 H8A 110.0 . . ? O1 C8 H8B 110.0 . . ? C7 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? N2 C9 C10 110.2(3) . . ? N2 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? N2 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? O2 C10 C9 106.7(2) . . ? O2 C10 H10A 110.4 . . ? C9 C10 H10A 110.4 . . ? O2 C10 H10B 110.4 . . ? C9 C10 H10B 110.4 . . ? H10A C10 H10B 108.6 . . ? O9 C11 H11A 109.5 . . ? O9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C11 O9 H9 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 N3 O3 Fe1 178.0(2) . . . . ? O5 N3 O3 Fe1 -2.5(3) . . . . ? C5 N1 C1 C2 -0.4(5) . . . . ? Fe1 N1 C1 C2 -171.9(3) . . . . ? N1 C1 C2 C3 -0.6(6) . . . . ? C1 C2 C3 C4 1.1(7) . . . . ? C2 C3 C4 C5 -0.4(6) . . . . ? C1 N1 C5 C4 1.1(5) . . . . ? Fe1 N1 C5 C4 172.8(3) . . . . ? C1 N1 C5 C6 178.9(3) . . . . ? Fe1 N1 C5 C6 -9.4(4) . . . . ? C3 C4 C5 N1 -0.6(5) . . . . ? C3 C4 C5 C6 -178.3(3) . . . . ? C7 N2 C6 C5 -149.3(3) . . . . ? C9 N2 C6 C5 86.1(3) . . . . ? Fe1 N2 C6 C5 -31.9(3) . . . . ? N1 C5 C6 N2 28.6(4) . . . . ? C4 C5 C6 N2 -153.6(3) . . . . ? C6 N2 C7 C8 160.5(3) . . . . ? C9 N2 C7 C8 -74.4(3) . . . . ? Fe1 N2 C7 C8 42.2(3) . . . . ? Fe1 O1 C8 C7 28.3(3) . . . . ? N2 C7 C8 O1 -46.3(3) . . . . ? C6 N2 C9 C10 -85.9(3) . . . . ? C7 N2 C9 C10 148.5(3) . . . . ? Fe1 N2 C9 C10 32.5(3) . . . . ? Fe1 O2 C10 C9 -157.4(2) 3_755 . . . ? Fe1 O2 C10 C9 42.7(3) . . . . ? N2 C9 C10 O2 -48.0(3) . . . . ? _refine_diff_density_max 1.599 _refine_diff_density_min -1.636 _refine_diff_density_rms 0.132 _database_code_depnum_ccdc_archive 'CCDC 912273' ####################################################################### # # 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_compd _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H28 Fe2 N10 O4' _chemical_formula_weight 584.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0010 '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 0.0050 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0090 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3390 0.7200 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.541(2) _cell_length_b 8.3690(17) _cell_length_c 13.436(3) _cell_angle_alpha 90 _cell_angle_beta 98.13(3) _cell_angle_gamma 90 _cell_volume 1173.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 30054 _cell_measurement_theta_min 0.37 _cell_measurement_theta_max 29.50 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_F_000 604 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.150 _exptl_absorpt_coefficient_mu 1.007 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.752 _exptl_absorpt_correction_T_max 0.864 _exptl_absorpt_process_details 'HKL3000 Scalapack' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.650 _diffrn_radiation_type synchrotron _diffrn_source 'PLSII 2D bending magnet' _diffrn_measurement_device_type 'ADSC Q210 CCD area detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15079 _diffrn_reflns_av_unetI/netI 0.0396 _diffrn_reflns_av_R_equivalents 0.0599 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.853 _diffrn_reflns_theta_max 29.542 _diffrn_reflns_theta_full 22.955 _diffrn_measured_fraction_theta_max 0.951 _diffrn_measured_fraction_theta_full 0.975 _diffrn_reflns_Laue_measured_fraction_max 0.951 _diffrn_reflns_Laue_measured_fraction_full 0.975 _diffrn_reflns_point_group_measured_fraction_max 0.951 _diffrn_reflns_point_group_measured_fraction_full 0.975 _reflns_number_total 4085 _reflns_number_gt 3779 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'PAL ADSC Quantum-210 ADX Program' _computing_cell_refinement HKL3000 _computing_data_reduction HKL3000 _computing_structure_solution 'SHELXS-2013 (sheldrick, 2013)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material WINGX _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.2598P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 4085 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.88796(2) 0.55478(2) 0.06128(2) 0.00773(6) Uani 1 1 d . . . . . O1 O 0.95505(9) 0.56272(9) 0.19712(6) 0.01412(16) Uani 1 1 d . . . . . O2 O 0.98516(8) 0.35894(8) 0.01541(6) 0.01111(14) Uani 1 1 d . . . . . N1 N 0.74397(9) 0.49320(11) -0.06679(7) 0.01219(16) Uani 1 1 d . . . . . N2 N 0.77860(9) 0.35058(11) 0.11600(7) 0.01116(15) Uani 1 1 d . . . . . N3 N 0.77775(10) 0.75679(12) 0.06935(8) 0.01717(18) Uani 1 1 d . . . . . N4 N 0.71664(10) 0.83037(11) 0.00280(8) 0.01616(18) Uani 1 1 d . . . . . N5 N 0.65617(16) 0.90642(17) -0.05813(10) 0.0350(3) Uani 1 1 d . . . . . C1 C 0.74498(13) 0.55414(12) -0.15975(9) 0.0162(2) Uani 1 1 d . . . . . H1 H 0.8127 0.6236 -0.1713 0.019 Uiso 1 1 calc R U . . . C2 C 0.64969(13) 0.51793(17) -0.23885(9) 0.0214(2) Uani 1 1 d . . . . . H2 H 0.6506 0.5646 -0.3032 0.026 Uiso 1 1 calc R U . . . C3 C 0.55325(13) 0.4125(2) -0.22245(10) 0.0257(3) Uani 1 1 d . . . . . H3 H 0.4875 0.3855 -0.2757 0.031 Uiso 1 1 calc R U . . . C4 C 0.55378(12) 0.34676(18) -0.12720(9) 0.0229(2) Uani 1 1 d . . . . . H4 H 0.4895 0.2728 -0.1147 0.028 Uiso 1 1 calc R U . . . C5 C 0.65058(10) 0.39155(14) -0.05056(8) 0.01439(19) Uani 1 1 d . . . . . C6 C 0.65111(11) 0.33387(15) 0.05598(9) 0.0175(2) Uani 1 1 d . . . . . H6A H 0.5879 0.3961 0.0879 0.021 Uiso 1 1 calc R U . . . H6B H 0.6249 0.2202 0.0550 0.021 Uiso 1 1 calc R U . . . C7 C 0.77415(11) 0.39930(14) 0.22195(8) 0.0161(2) Uani 1 1 d . . . . . H7A H 0.7513 0.3064 0.2614 0.019 Uiso 1 1 calc R U . . . H7B H 0.7082 0.4830 0.2242 0.019 Uiso 1 1 calc R U . . . C8 C 0.90542(12) 0.46336(13) 0.26664(8) 0.0152(2) Uani 1 1 d . . . . . H8A H 0.8977 0.5245 0.3286 0.018 Uiso 1 1 calc R U . . . H8B H 0.9648 0.3730 0.2849 0.018 Uiso 1 1 calc R U . . . C9 C 0.85759(11) 0.20471(12) 0.10983(8) 0.01420(19) Uani 1 1 d . . . . . H9A H 0.8025 0.1087 0.1081 0.017 Uiso 1 1 calc R U . . . H9B H 0.9234 0.1976 0.1700 0.017 Uiso 1 1 calc R U . . . C10 C 0.92234(11) 0.21053(11) 0.01569(8) 0.01211(18) Uani 1 1 d . . . . . H10A H 0.9849 0.1221 0.0163 0.015 Uiso 1 1 calc R U . . . H10B H 0.8578 0.1998 -0.0451 0.015 Uiso 1 1 calc R U . . . 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 0.01015(9) 0.00842(8) 0.00442(10) -0.00040(4) 0.00030(6) 0.00038(4) O1 0.0191(4) 0.0160(3) 0.0061(4) 0.0003(2) -0.0020(3) -0.0051(3) O2 0.0156(3) 0.0067(3) 0.0120(4) 0.0001(2) 0.0051(3) -0.0007(2) N1 0.0148(4) 0.0137(4) 0.0073(4) -0.0011(3) -0.0014(3) 0.0023(3) N2 0.0127(4) 0.0150(4) 0.0055(4) -0.0013(3) 0.0003(3) -0.0025(3) N3 0.0203(4) 0.0173(4) 0.0134(5) -0.0036(3) 0.0010(3) 0.0073(3) N4 0.0172(4) 0.0141(4) 0.0165(5) -0.0046(3) 0.0002(3) 0.0018(3) N5 0.0449(8) 0.0269(6) 0.0273(7) -0.0014(5) -0.0153(5) 0.0115(6) C1 0.0224(6) 0.0173(5) 0.0081(5) 0.0007(3) -0.0002(4) 0.0073(3) C2 0.0257(6) 0.0308(6) 0.0064(5) -0.0022(4) -0.0024(4) 0.0152(5) C3 0.0162(5) 0.0465(7) 0.0121(6) -0.0106(5) -0.0060(4) 0.0104(5) C4 0.0128(5) 0.0399(7) 0.0148(6) -0.0105(5) -0.0023(4) -0.0010(4) C5 0.0108(4) 0.0220(5) 0.0096(5) -0.0046(3) -0.0012(3) 0.0003(3) C6 0.0134(4) 0.0274(5) 0.0114(5) -0.0023(4) 0.0011(3) -0.0064(4) C7 0.0206(5) 0.0216(5) 0.0066(5) -0.0036(4) 0.0041(4) -0.0061(4) C8 0.0220(5) 0.0180(4) 0.0048(5) 0.0003(3) -0.0010(4) -0.0047(4) C9 0.0222(5) 0.0105(4) 0.0102(5) 0.0016(3) 0.0034(4) -0.0020(3) C10 0.0189(5) 0.0086(4) 0.0088(5) -0.0009(3) 0.0020(3) -0.0016(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 O1 1.8629(10) . ? Fe1 O2 1.9395(9) 3_765 ? Fe1 N3 2.0628(10) . ? Fe1 O2 2.0723(8) . ? Fe1 N1 2.1891(12) . ? Fe1 N2 2.2427(10) . ? O1 C8 1.4057(13) . ? O2 C10 1.4078(12) . ? O2 Fe1 1.9395(9) 3_765 ? N1 C5 1.3420(15) . ? N1 C1 1.3505(14) . ? N2 C6 1.4728(15) . ? N2 C9 1.4866(14) . ? N2 C7 1.4879(14) . ? N3 N4 1.1961(14) . ? N4 N5 1.1550(16) . ? C1 C2 1.3887(18) . ? C1 H1 0.9500 . ? C2 C3 1.387(2) . ? C2 H2 0.9500 . ? C3 C4 1.392(2) . ? C3 H3 0.9500 . ? C4 C5 1.3946(16) . ? C4 H4 0.9500 . ? C5 C6 1.5100(16) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5257(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5206(16) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 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 O1 Fe1 O2 108.21(4) . 3_765 ? O1 Fe1 N3 93.32(4) . . ? O2 Fe1 N3 99.12(4) 3_765 . ? O1 Fe1 O2 100.63(4) . . ? O2 Fe1 O2 74.30(4) 3_765 . ? N3 Fe1 O2 165.84(4) . . ? O1 Fe1 N1 154.62(4) . . ? O2 Fe1 N1 97.10(4) 3_765 . ? N3 Fe1 N1 84.33(4) . . ? O2 Fe1 N1 84.09(3) . . ? O1 Fe1 N2 81.23(4) . . ? O2 Fe1 N2 151.99(3) 3_765 . ? N3 Fe1 N2 106.73(4) . . ? O2 Fe1 N2 78.08(4) . . ? N1 Fe1 N2 75.34(4) . . ? C8 O1 Fe1 120.30(7) . . ? C10 O2 Fe1 133.62(6) . 3_765 ? C10 O2 Fe1 116.39(6) . . ? Fe1 O2 Fe1 105.70(4) 3_765 . ? C5 N1 C1 119.44(10) . . ? C5 N1 Fe1 117.68(7) . . ? C1 N1 Fe1 122.88(8) . . ? C6 N2 C9 111.49(9) . . ? C6 N2 C7 113.58(9) . . ? C9 N2 C7 111.84(9) . . ? C6 N2 Fe1 111.37(7) . . ? C9 N2 Fe1 106.83(6) . . ? C7 N2 Fe1 101.07(6) . . ? N4 N3 Fe1 129.09(8) . . ? N5 N4 N3 176.79(13) . . ? N1 C1 C2 121.73(12) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C3 C2 C1 118.97(12) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 119.31(12) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 118.68(13) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? N1 C5 C4 121.82(11) . . ? N1 C5 C6 116.89(10) . . ? C4 C5 C6 121.22(11) . . ? N2 C6 C5 111.68(9) . . ? N2 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N2 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? N2 C7 C8 108.86(9) . . ? N2 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? N2 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? O1 C8 C7 110.39(10) . . ? O1 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? O1 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N2 C9 C10 109.93(8) . . ? N2 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? N2 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? O2 C10 C9 107.28(8) . . ? O2 C10 H10A 110.3 . . ? C9 C10 H10A 110.3 . . ? O2 C10 H10B 110.3 . . ? C9 C10 H10B 110.3 . . ? H10A C10 H10B 108.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Fe1 O1 C8 -158.87(8) 3_765 . . . ? N3 Fe1 O1 C8 100.39(9) . . . . ? O2 Fe1 O1 C8 -82.06(9) . . . . ? N1 Fe1 O1 C8 16.63(13) . . . . ? N2 Fe1 O1 C8 -6.04(8) . . . . ? C5 N1 C1 C2 1.81(16) . . . . ? Fe1 N1 C1 C2 -177.47(8) . . . . ? N1 C1 C2 C3 -2.01(17) . . . . ? C1 C2 C3 C4 0.48(19) . . . . ? C2 C3 C4 C5 1.14(19) . . . . ? C1 N1 C5 C4 -0.09(16) . . . . ? Fe1 N1 C5 C4 179.23(9) . . . . ? C1 N1 C5 C6 -177.12(10) . . . . ? Fe1 N1 C5 C6 2.20(13) . . . . ? C3 C4 C5 N1 -1.38(18) . . . . ? C3 C4 C5 C6 175.52(11) . . . . ? C9 N2 C6 C5 -90.09(11) . . . . ? C7 N2 C6 C5 142.45(10) . . . . ? Fe1 N2 C6 C5 29.14(11) . . . . ? N1 C5 C6 N2 -21.38(14) . . . . ? C4 C5 C6 N2 161.57(11) . . . . ? C6 N2 C7 C8 -162.26(9) . . . . ? C9 N2 C7 C8 70.46(11) . . . . ? Fe1 N2 C7 C8 -42.89(10) . . . . ? Fe1 O1 C8 C7 -17.61(12) . . . . ? N2 C7 C8 O1 42.76(12) . . . . ? C6 N2 C9 C10 83.75(11) . . . . ? C7 N2 C9 C10 -147.85(9) . . . . ? Fe1 N2 C9 C10 -38.14(10) . . . . ? Fe1 O2 C10 C9 166.89(8) 3_765 . . . ? Fe1 O2 C10 C9 -40.23(11) . . . . ? N2 C9 C10 O2 51.55(12) . . . . ? _refine_diff_density_max 0.826 _refine_diff_density_min -1.411 _refine_diff_density_rms 0.321 _database_code_depnum_ccdc_archive 'CCDC 955381'