# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Mary Pryce' _publ_contact_author_email MARY.PRYCE@DCU.IE _publ_section_title ; Visible Light Driven Room Temperature Pauson-Khand Reaction ; loop_ _publ_author_name 'Mary Pryce' 'Wesley Browne' 'Anthony C. Coleman' 'Ben Feringa' 'Conor Long' 'Auke Meetsma' # Attachment 'q14241.cif' # CIF-file generated for C20H20FeO P-1 q1424 #============================================================================== data_q14241.cif _database_code_depnum_ccdc_archive 'CCDC 699252' _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 Fe O' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C20 H20 Fe O' _chemical_formula_iupac ? _chemical_formula_weight 332.22 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 8.7216(12) _cell_length_b 10.2643(14) _cell_length_c 10.3445(14) _cell_angle_alpha 60.6174(14) _cell_angle_beta 88.8587(16) _cell_angle_gamma 69.6825(15) _cell_volume 743.79(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 3804 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 29.30 _cell_special_details ; The final unit cell was obtained from the xyz centroids of 3804 reflections after integration using the SAINTPLUS software package (Bruker, 2007). Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the final atomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988) ; _exptl_crystal_description 'cut fragment' _exptl_crystal_colour red _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.33 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 1.012 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS, (Bruker, 2007))' _exptl_absorpt_correction_T_min 0.6114 _exptl_absorpt_correction_T_max 0.7160 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed Siemens Mo tube ' _diffrn_radiation_monochromator 'parallel mounted graphite' _diffrn_radiation_detector ; CCD area-detector ; _diffrn_measurement_device_type ; Bruker Smart Apex; CCD area detector ; _diffrn_measurement_method '\f and \w scans' _diffrn_special_details ; Crystal into the cold nitrogen stream of the low-temparature unit (KRYOFLEX, (Bruker, 2006)). ; _diffrn_detector_area_resol_mean 66.06 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 6709 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 28.28 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.978 _diffrn_reflns_reduction_process ; Intensity data were corrected for Lorentz and polarization effects, decay and absorption and reduced to F~o~^2^ using SAINT-Plus & SADABS (Bruker, 2007). ; # number of unique reflections _reflns_number_total 3536 _reflns_number_gt 3182 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2007)' _computing_data_reduction SAINT-Plus _computing_structure_solution ; DIRDIF-07 (Beurskens et al., 2007) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek, 2003) PLUTO (Meetsma, 2007) ; _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0468P)^2^+0.1640P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary direct _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _chemical_absolute_configuration . _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3536 _refine_ls_number_parameters 279 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.482 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.077 _vrn_publ_code_number_frames 1800 _vrn_publ_code_frame_time_sec 5.0 _vrn_publ_code_meas_time_hour 5.4 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Fe Fe Uani 1.15564(3) 0.22198(3) 0.42084(3) 1.000 0.0140(1) . . O O Uani 0.66646(17) 0.31074(16) 0.42166(16) 1.000 0.0286(4) . . C1 C Uani 1.2511(2) 0.3129(2) 0.5225(2) 1.000 0.0197(5) . . C2 C Uani 1.3721(2) 0.1627(2) 0.5492(2) 1.000 0.0199(5) . . C3 C Uani 1.3046(2) 0.0417(2) 0.6252(2) 1.000 0.0188(5) . . C4 C Uani 1.1427(2) 0.1173(2) 0.64614(19) 1.000 0.0171(5) . . C5 C Uani 1.1098(2) 0.2850(2) 0.58219(19) 1.000 0.0165(5) . . C6 C Uani 1.0935(2) 0.3836(2) 0.1925(2) 1.000 0.0183(5) . . C7 C Uani 1.2156(2) 0.2309(2) 0.2259(2) 1.000 0.0207(5) . . C8 C Uani 1.1490(2) 0.1103(2) 0.3044(2) 1.000 0.0208(5) . . C9 C Uani 0.9854(2) 0.1869(2) 0.3213(2) 1.000 0.0176(5) . . C10 C Uani 0.9490(2) 0.3577(2) 0.25126(19) 1.000 0.0153(5) . . C11 C Uani 0.7936(2) 0.4813(2) 0.24015(19) 1.000 0.0149(5) . . C12 C Uani 0.6612(2) 0.4444(2) 0.3269(2) 1.000 0.0171(5) . . C13 C Uani 0.5139(2) 0.6035(2) 0.2772(2) 1.000 0.0163(5) . . C14 C Uani 0.5718(2) 0.7374(2) 0.16298(19) 1.000 0.0153(4) . . C15 C Uani 0.7416(2) 0.6439(2) 0.15071(19) 1.000 0.0152(5) . . C16 C Uani 0.3617(2) 0.6251(2) 0.1826(2) 1.000 0.0203(5) . . C17 C Uani 0.2176(3) 0.7770(2) 0.1612(2) 1.000 0.0262(6) . . C18 C Uani 0.2732(2) 0.9170(2) 0.0534(2) 1.000 0.0219(5) . . C19 C Uani 0.4374(2) 0.8291(2) 0.0194(2) 1.000 0.0165(5) . . C20 C Uani 0.4048(2) 0.6893(2) 0.0230(2) 1.000 0.0188(5) . . H1 H Uiso 1.258(3) 0.417(3) 0.469(3) 1.000 0.032(6) . . H2 H Uiso 1.479(3) 0.148(3) 0.518(2) 1.000 0.026(6) . . H3 H Uiso 1.354(3) -0.073(3) 0.655(2) 1.000 0.024(6) . . H4 H Uiso 1.068(3) 0.063(3) 0.693(2) 1.000 0.023(5) . . H5 H Uiso 1.014(3) 0.360(3) 0.584(3) 1.000 0.030(6) . . H6 H Uiso 1.105(3) 0.482(3) 0.142(2) 1.000 0.023(5) . . H7 H Uiso 1.326(3) 0.213(3) 0.202(2) 1.000 0.024(6) . . H8 H Uiso 1.206(3) -0.008(3) 0.347(3) 1.000 0.027(6) . . H9 H Uiso 0.914(3) 0.134(3) 0.375(2) 1.000 0.021(5) . . H13 H Uiso 0.488(3) 0.607(2) 0.364(2) 1.000 0.021(5) . . H14 H Uiso 0.578(2) 0.809(2) 0.197(2) 1.000 0.011(5) . . H15 H Uiso 0.803(2) 0.697(2) 0.082(2) 1.000 0.017(5) . . H16 H Uiso 0.335(3) 0.529(2) 0.224(2) 1.000 0.020(5) . . H17 H Uiso 0.200(3) 0.778(3) 0.254(3) 1.000 0.035(6) . . H17' H Uiso 0.116(3) 0.783(3) 0.118(3) 1.000 0.033(6) . . H18 H Uiso 0.288(3) 0.974(2) 0.099(2) 1.000 0.020(5) . . H18' H Uiso 0.189(3) 0.990(3) -0.038(2) 1.000 0.023(5) . . H19 H Uiso 0.471(2) 0.899(2) -0.069(2) 1.000 0.013(5) . . H20 H Uiso 0.500(3) 0.615(3) 0.013(2) 1.000 0.017(5) . . H20' H Uiso 0.316(3) 0.723(3) -0.053(3) 1.000 0.033(6) . . 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 Fe 0.0130(1) 0.0159(1) 0.0113(1) -0.0066(1) 0.0011(1) -0.0040(1) O 0.0232(7) 0.0171(6) 0.0293(8) -0.0014(6) 0.0085(6) -0.0067(5) C1 0.0247(10) 0.0238(9) 0.0141(9) -0.0098(8) 0.0027(7) -0.0129(8) C2 0.0145(9) 0.0313(10) 0.0142(9) -0.0126(8) 0.0013(7) -0.0077(7) C3 0.0174(9) 0.0191(8) 0.0126(8) -0.0073(7) -0.0019(7) -0.0005(7) C4 0.0187(9) 0.0189(8) 0.0119(8) -0.0069(7) 0.0027(7) -0.0069(7) C5 0.0188(9) 0.0177(8) 0.0131(8) -0.0089(7) 0.0029(7) -0.0056(7) C6 0.0179(9) 0.0207(8) 0.0109(8) -0.0053(7) 0.0001(7) -0.0060(7) C7 0.0141(9) 0.0302(10) 0.0128(9) -0.0118(8) 0.0012(7) -0.0020(7) C8 0.0199(9) 0.0208(8) 0.0183(9) -0.0126(8) -0.0033(7) 0.0000(7) C9 0.0182(9) 0.0179(8) 0.0161(9) -0.0093(7) -0.0008(7) -0.0052(7) C10 0.0141(8) 0.0166(8) 0.0116(8) -0.0062(7) -0.0009(6) -0.0035(6) C11 0.0140(8) 0.0164(8) 0.0118(8) -0.0059(7) 0.0001(6) -0.0053(6) C12 0.0156(8) 0.0169(8) 0.0147(8) -0.0055(7) 0.0012(7) -0.0059(7) C13 0.0152(8) 0.0182(8) 0.0115(8) -0.0053(7) 0.0030(7) -0.0058(7) C14 0.0164(8) 0.0137(7) 0.0130(8) -0.0058(7) 0.0011(7) -0.0044(6) C15 0.0148(8) 0.0165(8) 0.0121(8) -0.0059(7) 0.0009(7) -0.0058(7) C16 0.0162(9) 0.0199(8) 0.0202(9) -0.0078(8) 0.0023(7) -0.0060(7) C17 0.0154(9) 0.0270(10) 0.0253(11) -0.0097(9) 0.0034(8) -0.0024(8) C18 0.0183(9) 0.0183(8) 0.0200(10) -0.0086(8) 0.0009(8) 0.0009(7) C19 0.0172(9) 0.0139(7) 0.0127(8) -0.0047(7) 0.0009(7) -0.0031(7) C20 0.0166(9) 0.0198(8) 0.0191(9) -0.0109(8) -0.0001(7) -0.0046(7) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe C1 2.051(2) . . yes Fe C2 2.0510(19) . . yes Fe C3 2.0451(19) . . yes Fe C4 2.0532(17) . . yes Fe C5 2.054(2) . . yes Fe C6 2.0510(18) . . yes Fe C7 2.0392(19) . . yes Fe C8 2.043(2) . . yes Fe C9 2.047(2) . . yes Fe C10 2.0617(18) . . yes O C12 1.218(3) . . yes C1 C2 1.425(3) . . no C1 C5 1.422(3) . . no C2 C3 1.428(3) . . no C3 C4 1.426(3) . . no C4 C5 1.425(3) . . no C6 C7 1.426(3) . . no C6 C10 1.440(3) . . no C7 C8 1.422(3) . . no C8 C9 1.425(3) . . no C9 C10 1.441(3) . . no C10 C11 1.459(3) . . no C11 C12 1.487(3) . . no C11 C15 1.350(3) . . no C12 C13 1.526(3) . . no C13 C14 1.551(3) . . no C13 C16 1.550(3) . . no C14 C15 1.502(3) . . no C14 C19 1.548(3) . . no C16 C17 1.540(3) . . no C16 C20 1.543(3) . . no C17 C18 1.560(3) . . no C18 C19 1.544(3) . . no C19 C20 1.540(3) . . no C1 H1 0.96(3) . . no C2 H2 0.97(3) . . no C3 H3 0.98(3) . . no C4 H4 0.97(3) . . no C5 H5 0.93(3) . . no C6 H6 0.92(3) . . no C7 H7 0.97(3) . . no C8 H8 0.99(3) . . no C9 H9 0.96(3) . . no C13 H13 0.94(2) . . no C14 H14 0.97(2) . . no C15 H15 0.947(19) . . no C16 H16 0.98(2) . . no C17 H17 0.97(3) . . no C17 H17' 0.97(3) . . no C18 H18 0.95(2) . . no C18 H18' 0.97(2) . . no C19 H19 0.964(18) . . no C20 H20 0.96(3) . . no C20 H20' 0.95(3) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Fe C2 40.65(8) . . . yes C1 Fe C3 68.47(8) . . . yes C1 Fe C4 68.32(8) . . . yes C1 Fe C5 40.55(7) . . . yes C1 Fe C6 108.85(8) . . . yes C1 Fe C7 123.40(8) . . . yes C1 Fe C8 158.53(8) . . . yes C1 Fe C9 160.00(8) . . . yes C1 Fe C10 124.21(8) . . . yes C2 Fe C3 40.80(8) . . . yes C2 Fe C4 68.49(7) . . . yes C2 Fe C5 68.38(8) . . . yes C2 Fe C6 122.89(7) . . . yes C2 Fe C7 106.63(8) . . . yes C2 Fe C8 121.43(8) . . . yes C2 Fe C9 157.49(9) . . . yes C2 Fe C10 159.77(8) . . . yes C3 Fe C4 40.74(8) . . . yes C3 Fe C5 68.45(8) . . . yes C3 Fe C6 158.02(8) . . . yes C3 Fe C7 121.07(8) . . . yes C3 Fe C8 105.40(8) . . . yes C3 Fe C9 121.31(8) . . . yes C3 Fe C10 158.58(8) . . . yes C4 Fe C5 40.60(8) . . . yes C4 Fe C6 160.39(8) . . . yes C4 Fe C7 157.19(9) . . . yes C4 Fe C8 121.29(8) . . . yes C4 Fe C9 106.77(7) . . . yes C4 Fe C10 123.33(7) . . . yes C5 Fe C6 124.66(8) . . . yes C5 Fe C7 160.29(8) . . . yes C5 Fe C8 158.25(8) . . . yes C5 Fe C9 123.24(8) . . . yes C5 Fe C10 108.83(8) . . . yes C6 Fe C7 40.81(8) . . . yes C6 Fe C8 68.71(8) . . . yes C6 Fe C9 68.89(8) . . . yes C6 Fe C10 40.97(7) . . . yes C7 Fe C8 40.79(8) . . . yes C7 Fe C9 68.74(8) . . . yes C7 Fe C10 68.88(8) . . . yes C8 Fe C9 40.78(8) . . . yes C8 Fe C10 68.87(8) . . . yes C9 Fe C10 41.05(8) . . . yes Fe C1 C2 69.67(12) . . . yes Fe C1 C5 69.82(11) . . . yes C2 C1 C5 108.21(18) . . . no Fe C2 C1 69.68(11) . . . yes Fe C2 C3 69.38(11) . . . yes C1 C2 C3 107.77(17) . . . no Fe C3 C2 69.83(11) . . . yes Fe C3 C4 69.94(10) . . . yes C2 C3 C4 108.04(18) . . . no Fe C4 C3 69.33(10) . . . yes Fe C4 C5 69.72(10) . . . yes C3 C4 C5 107.90(17) . . . no Fe C5 C1 69.63(11) . . . yes Fe C5 C4 69.68(11) . . . yes C1 C5 C4 108.07(18) . . . no Fe C6 C7 69.15(10) . . . yes Fe C6 C10 69.91(10) . . . yes C7 C6 C10 108.05(17) . . . no Fe C7 C6 70.04(11) . . . yes Fe C7 C8 69.73(11) . . . yes C6 C7 C8 108.38(17) . . . no Fe C8 C7 69.48(12) . . . yes Fe C8 C9 69.78(12) . . . yes C7 C8 C9 108.23(18) . . . no Fe C9 C8 69.44(11) . . . yes Fe C9 C10 70.02(11) . . . yes C8 C9 C10 108.16(17) . . . no Fe C10 C6 69.12(10) . . . yes Fe C10 C9 68.93(10) . . . yes Fe C10 C11 127.79(13) . . . yes C6 C10 C9 107.18(18) . . . no C6 C10 C11 126.55(18) . . . no C9 C10 C11 126.26(17) . . . no C10 C11 C12 123.88(17) . . . no C10 C11 C15 127.87(17) . . . no C12 C11 C15 108.24(18) . . . no O C12 C11 126.70(19) . . . yes O C12 C13 124.76(18) . . . yes C11 C12 C13 108.54(16) . . . no C12 C13 C14 104.90(15) . . . no C12 C13 C16 112.83(17) . . . no C14 C13 C16 103.74(14) . . . no C13 C14 C15 103.71(16) . . . no C13 C14 C19 102.70(15) . . . no C15 C14 C19 114.82(15) . . . no C11 C15 C14 114.51(16) . . . no C13 C16 C17 106.37(17) . . . no C13 C16 C20 102.76(15) . . . no C17 C16 C20 101.13(15) . . . no C16 C17 C18 102.75(18) . . . no C17 C18 C19 103.53(17) . . . no C14 C19 C18 107.27(15) . . . no C14 C19 C20 101.83(16) . . . no C18 C19 C20 101.75(15) . . . no C16 C20 C19 94.40(15) . . . no Fe C1 H1 123.5(17) . . . no C2 C1 H1 127.3(18) . . . no C5 C1 H1 124.4(18) . . . no Fe C2 H2 125.0(12) . . . no C1 C2 H2 125.3(17) . . . no C3 C2 H2 127.0(18) . . . no Fe C3 H3 123.5(12) . . . no C2 C3 H3 128.2(16) . . . no C4 C3 H3 123.7(16) . . . no Fe C4 H4 124.9(12) . . . no C3 C4 H4 125.2(18) . . . no C5 C4 H4 126.9(18) . . . no Fe C5 H5 128.2(17) . . . no C1 C5 H5 127.1(18) . . . no C4 C5 H5 124.8(18) . . . no Fe C6 H6 126.5(13) . . . no C7 C6 H6 126.0(18) . . . no C10 C6 H6 125.9(18) . . . no Fe C7 H7 124.3(13) . . . no C6 C7 H7 125.3(17) . . . no C8 C7 H7 126.3(17) . . . no Fe C8 H8 123.5(16) . . . no C7 C8 H8 127.4(16) . . . no C9 C8 H8 124.3(16) . . . no Fe C9 H9 123.4(13) . . . no C8 C9 H9 126.3(18) . . . no C10 C9 H9 125.4(18) . . . no C12 C13 H13 107.6(13) . . . no C14 C13 H13 115.6(15) . . . no C16 C13 H13 112.0(16) . . . no C13 C14 H14 113.0(11) . . . no C15 C14 H14 110.5(11) . . . no C19 C14 H14 111.7(11) . . . no C11 C15 H15 124.1(13) . . . no C14 C15 H15 121.4(13) . . . no C13 C16 H16 114.3(13) . . . no C17 C16 H16 114.0(15) . . . no C20 C16 H16 116.8(11) . . . no C16 C17 H17 114.4(18) . . . no C16 C17 H17' 108(2) . . . no C18 C17 H17 110.1(18) . . . no C18 C17 H17' 113.7(17) . . . no H17 C17 H17' 108(2) . . . no C17 C18 H18 111.9(12) . . . no C17 C18 H18' 107.9(16) . . . no C19 C18 H18 112.2(16) . . . no C19 C18 H18' 110.5(16) . . . no H18 C18 H18' 111(2) . . . no C14 C19 H19 112.1(11) . . . no C18 C19 H19 114.3(13) . . . no C20 C19 H19 118.2(13) . . . no C16 C20 H20 115.1(11) . . . no C16 C20 H20' 113.6(17) . . . no C19 C20 H20 113.0(18) . . . no C19 C20 H20' 114.6(19) . . . no H20 C20 H20' 106(2) . . . no 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 C2 Fe C1 C5 -119.42(15) . . . . no C3 Fe C1 C2 37.84(11) . . . . no C3 Fe C1 C5 -81.59(12) . . . . no C4 Fe C1 C2 81.81(12) . . . . no C4 Fe C1 C5 -37.62(11) . . . . no C5 Fe C1 C2 119.42(15) . . . . no C6 Fe C1 C2 -118.89(11) . . . . no C6 Fe C1 C5 121.68(12) . . . . no C7 Fe C1 C2 -76.02(13) . . . . no C7 Fe C1 C5 164.56(11) . . . . no C8 Fe C1 C2 -39.3(2) . . . . no C8 Fe C1 C5 -158.70(19) . . . . no C9 Fe C1 C2 161.2(2) . . . . no C9 Fe C1 C5 41.8(3) . . . . no C10 Fe C1 C2 -161.79(10) . . . . no C10 Fe C1 C5 78.79(13) . . . . no C1 Fe C2 C3 119.15(16) . . . . no C3 Fe C2 C1 -119.15(16) . . . . no C4 Fe C2 C1 -81.33(12) . . . . no C4 Fe C2 C3 37.82(12) . . . . no C5 Fe C2 C1 -37.52(11) . . . . no C5 Fe C2 C3 81.63(12) . . . . no C6 Fe C2 C1 80.65(13) . . . . no C6 Fe C2 C3 -160.20(12) . . . . no C7 Fe C2 C1 122.28(11) . . . . no C7 Fe C2 C3 -118.57(12) . . . . no C8 Fe C2 C1 164.25(10) . . . . no C8 Fe C2 C3 -76.60(13) . . . . no C9 Fe C2 C1 -163.25(18) . . . . no C9 Fe C2 C3 -44.1(2) . . . . no C10 Fe C2 C1 48.4(3) . . . . no C10 Fe C2 C3 167.5(2) . . . . no C1 Fe C3 C2 -37.71(12) . . . . no C1 Fe C3 C4 81.34(13) . . . . no C2 Fe C3 C4 119.05(17) . . . . no C4 Fe C3 C2 -119.05(17) . . . . no C5 Fe C3 C2 -81.45(13) . . . . no C5 Fe C3 C4 37.59(12) . . . . no C6 Fe C3 C2 49.5(3) . . . . no C6 Fe C3 C4 168.5(2) . . . . no C7 Fe C3 C2 79.24(14) . . . . no C7 Fe C3 C4 -161.72(12) . . . . no C8 Fe C3 C2 120.57(12) . . . . no C8 Fe C3 C4 -120.38(12) . . . . no C9 Fe C3 C2 161.83(12) . . . . no C9 Fe C3 C4 -79.12(14) . . . . no C10 Fe C3 C2 -168.2(2) . . . . no C10 Fe C3 C4 -49.2(3) . . . . no C1 Fe C4 C3 -81.75(13) . . . . no C1 Fe C4 C5 37.57(11) . . . . no C2 Fe C4 C3 -37.88(12) . . . . no C2 Fe C4 C5 81.45(12) . . . . no C3 Fe C4 C5 119.32(16) . . . . no C5 Fe C4 C3 -119.32(16) . . . . no C7 Fe C4 C3 43.9(2) . . . . no C7 Fe C4 C5 163.20(18) . . . . no C8 Fe C4 C3 76.73(14) . . . . no C8 Fe C4 C5 -163.95(11) . . . . no C9 Fe C4 C3 118.80(13) . . . . no C9 Fe C4 C5 -121.87(12) . . . . no C10 Fe C4 C3 160.69(12) . . . . no C10 Fe C4 C5 -79.99(13) . . . . no C1 Fe C5 C4 -119.36(16) . . . . no C2 Fe C5 C1 37.62(11) . . . . no C2 Fe C5 C4 -81.74(12) . . . . no C3 Fe C5 C1 81.65(12) . . . . no C3 Fe C5 C4 -37.72(11) . . . . no C4 Fe C5 C1 119.36(16) . . . . no C6 Fe C5 C1 -78.24(13) . . . . no C6 Fe C5 C4 162.40(11) . . . . no C8 Fe C5 C1 158.97(19) . . . . no C8 Fe C5 C4 39.6(3) . . . . no C9 Fe C5 C1 -164.20(11) . . . . no C9 Fe C5 C4 76.44(13) . . . . no C10 Fe C5 C1 -121.02(12) . . . . no C10 Fe C5 C4 119.63(11) . . . . no C1 Fe C6 C7 119.64(12) . . . . no C1 Fe C6 C10 -120.86(13) . . . . no C2 Fe C6 C7 76.86(14) . . . . no C2 Fe C6 C10 -163.65(12) . . . . no C3 Fe C6 C7 40.6(3) . . . . no C3 Fe C6 C10 160.1(2) . . . . no C5 Fe C6 C7 161.91(11) . . . . no C5 Fe C6 C10 -78.60(14) . . . . no C7 Fe C6 C10 119.49(17) . . . . no C8 Fe C6 C7 -37.63(11) . . . . no C8 Fe C6 C10 81.87(13) . . . . no C9 Fe C6 C7 -81.52(12) . . . . no C9 Fe C6 C10 37.98(12) . . . . no C10 Fe C6 C7 -119.49(17) . . . . no C1 Fe C7 C6 -80.13(13) . . . . no C1 Fe C7 C8 160.42(11) . . . . no C2 Fe C7 C6 -121.41(12) . . . . no C2 Fe C7 C8 119.14(12) . . . . no C3 Fe C7 C6 -163.47(11) . . . . no C3 Fe C7 C8 77.08(13) . . . . no C4 Fe C7 C6 164.65(18) . . . . no C4 Fe C7 C8 45.2(2) . . . . no C6 Fe C7 C8 -119.45(16) . . . . no C8 Fe C7 C6 119.45(16) . . . . no C9 Fe C7 C6 81.90(12) . . . . no C9 Fe C7 C8 -37.55(11) . . . . no C10 Fe C7 C6 37.72(11) . . . . no C10 Fe C7 C8 -81.73(12) . . . . no C1 Fe C8 C7 -49.9(3) . . . . no C1 Fe C8 C9 -169.46(19) . . . . no C2 Fe C8 C7 -78.76(13) . . . . no C2 Fe C8 C9 161.64(11) . . . . no C3 Fe C8 C7 -120.01(12) . . . . no C3 Fe C8 C9 120.40(11) . . . . no C4 Fe C8 C7 -161.22(11) . . . . no C4 Fe C8 C9 79.19(13) . . . . no C5 Fe C8 C7 169.73(19) . . . . no C5 Fe C8 C9 50.1(2) . . . . no C6 Fe C8 C7 37.65(11) . . . . no C6 Fe C8 C9 -81.95(12) . . . . no C7 Fe C8 C9 -119.60(16) . . . . no C9 Fe C8 C7 119.60(16) . . . . no C10 Fe C8 C7 81.75(12) . . . . no C10 Fe C8 C9 -37.85(11) . . . . no C1 Fe C9 C8 168.71(19) . . . . no C1 Fe C9 C10 49.3(3) . . . . no C2 Fe C9 C8 -44.6(2) . . . . no C2 Fe C9 C10 -163.97(17) . . . . no C3 Fe C9 C8 -76.75(13) . . . . no C3 Fe C9 C10 163.88(11) . . . . no C4 Fe C9 C8 -118.76(12) . . . . no C4 Fe C9 C10 121.86(11) . . . . no C5 Fe C9 C8 -160.12(11) . . . . no C5 Fe C9 C10 80.50(13) . . . . no C6 Fe C9 C8 81.47(12) . . . . no C6 Fe C9 C10 -37.91(11) . . . . no C7 Fe C9 C8 37.55(11) . . . . no C7 Fe C9 C10 -81.83(12) . . . . no C8 Fe C9 C10 -119.38(15) . . . . no C10 Fe C9 C8 119.38(15) . . . . no C1 Fe C10 C6 79.22(14) . . . . no C1 Fe C10 C9 -161.72(11) . . . . no C1 Fe C10 C11 -41.5(2) . . . . no C2 Fe C10 C6 43.1(3) . . . . no C2 Fe C10 C9 162.2(2) . . . . no C2 Fe C10 C11 -77.6(3) . . . . no C3 Fe C10 C6 -159.6(2) . . . . no C3 Fe C10 C9 -40.5(3) . . . . no C3 Fe C10 C11 79.7(3) . . . . no C4 Fe C10 C6 164.19(12) . . . . no C4 Fe C10 C9 -76.74(14) . . . . no C4 Fe C10 C11 43.5(2) . . . . no C5 Fe C10 C6 121.58(13) . . . . no C5 Fe C10 C9 -119.36(11) . . . . no C5 Fe C10 C11 0.86(19) . . . . no C6 Fe C10 C9 119.06(17) . . . . no C6 Fe C10 C11 -120.7(2) . . . . no C7 Fe C10 C6 -37.58(12) . . . . no C7 Fe C10 C9 81.48(12) . . . . no C7 Fe C10 C11 -158.3(2) . . . . no C8 Fe C10 C6 -81.46(13) . . . . no C8 Fe C10 C9 37.61(11) . . . . no C8 Fe C10 C11 157.83(19) . . . . no C9 Fe C10 C6 -119.06(17) . . . . no C9 Fe C10 C11 120.2(2) . . . . no Fe C1 C2 C3 -59.13(13) . . . . no C5 C1 C2 Fe 59.39(13) . . . . no C5 C1 C2 C3 0.3(2) . . . . no Fe C1 C5 C4 59.29(13) . . . . no C2 C1 C5 Fe -59.29(13) . . . . no C2 C1 C5 C4 0.0(2) . . . . no Fe C2 C3 C4 -59.73(13) . . . . no C1 C2 C3 Fe 59.32(13) . . . . no C1 C2 C3 C4 -0.4(2) . . . . no Fe C3 C4 C5 -59.25(12) . . . . no C2 C3 C4 Fe 59.66(13) . . . . no C2 C3 C4 C5 0.4(2) . . . . no Fe C4 C5 C1 -59.26(13) . . . . no C3 C4 C5 Fe 59.01(12) . . . . no C3 C4 C5 C1 -0.3(2) . . . . no Fe C6 C7 C8 59.40(13) . . . . no C10 C6 C7 Fe -59.29(13) . . . . no C10 C6 C7 C8 0.1(2) . . . . no Fe C6 C10 C9 -58.62(12) . . . . no Fe C6 C10 C11 122.24(19) . . . . no C7 C6 C10 Fe 58.82(13) . . . . no C7 C6 C10 C9 0.2(2) . . . . no C7 C6 C10 C11 -178.94(17) . . . . no Fe C7 C8 C9 59.21(13) . . . . no C6 C7 C8 Fe -59.59(13) . . . . no C6 C7 C8 C9 -0.4(2) . . . . no Fe C8 C9 C10 59.53(13) . . . . no C7 C8 C9 Fe -59.03(13) . . . . no C7 C8 C9 C10 0.5(2) . . . . no Fe C9 C10 C6 58.74(12) . . . . no Fe C9 C10 C11 -122.13(18) . . . . no C8 C9 C10 Fe -59.17(13) . . . . no C8 C9 C10 C6 -0.4(2) . . . . no C8 C9 C10 C11 178.71(17) . . . . no Fe C10 C11 C12 -77.3(2) . . . . no Fe C10 C11 C15 104.5(2) . . . . no C6 C10 C11 C12 -168.07(18) . . . . no C6 C10 C11 C15 13.7(3) . . . . no C9 C10 C11 C12 13.0(3) . . . . no C9 C10 C11 C15 -165.23(19) . . . . no C10 C11 C12 O 3.6(3) . . . . no C10 C11 C12 C13 -176.10(17) . . . . no C15 C11 C12 O -177.9(2) . . . . no C15 C11 C12 C13 2.4(2) . . . . no C10 C11 C15 C14 178.12(18) . . . . no C12 C11 C15 C14 -0.3(2) . . . . no O C12 C13 C14 176.85(19) . . . . no O C12 C13 C16 -70.9(2) . . . . no C11 C12 C13 C14 -3.4(2) . . . . no C11 C12 C13 C16 108.83(17) . . . . no C12 C13 C14 C15 3.09(19) . . . . no C12 C13 C14 C19 122.95(16) . . . . no C16 C13 C14 C15 -115.49(16) . . . . no C16 C13 C14 C19 4.4(2) . . . . no C12 C13 C16 C17 172.08(15) . . . . no C12 C13 C16 C20 -82.09(19) . . . . no C14 C13 C16 C17 -74.96(18) . . . . no C14 C13 C16 C20 30.9(2) . . . . no C13 C14 C15 C11 -1.9(2) . . . . no C19 C14 C15 C11 -113.08(19) . . . . no C13 C14 C19 C18 68.2(2) . . . . no C13 C14 C19 C20 -38.26(19) . . . . no C15 C14 C19 C18 -179.98(17) . . . . no C15 C14 C19 C20 73.58(19) . . . . no C13 C16 C17 C18 69.29(17) . . . . no C20 C16 C17 C18 -37.71(18) . . . . no C13 C16 C20 C19 -52.90(18) . . . . no C17 C16 C20 C19 56.92(17) . . . . no C16 C17 C18 C19 2.99(18) . . . . no C17 C18 C19 C14 -73.65(19) . . . . no C17 C18 C19 C20 32.84(17) . . . . no C14 C19 C20 C16 55.85(16) . . . . no C18 C19 C20 C16 -54.84(16) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Fe C12 3.988(2) . . no Fe H9 3.48(3) . 2_756 no O C2 3.354(3) . 1_455 no O C9 3.026(3) . . no O H2 2.58(3) . 1_455 no O H9 2.51(3) . . no O H8 2.65(3) . 2_756 no O H13 2.89(2) . 2_666 no C1 C3 2.305(3) . . no C1 C4 2.305(3) . . no C1 C6 3.337(3) . . no C1 C13 3.517(3) . 2_766 no C1 C14 3.352(3) . 2_766 no C2 C4 2.310(3) . . no C2 O 3.354(3) . 1_655 no C2 C8 3.570(3) . . no C2 C5 2.307(3) . . no C2 C7 3.280(3) . . no C3 C19 3.526(3) . 1_646 no C3 C5 2.305(3) . . no C3 C9 3.567(3) . . no C3 C8 3.252(3) . . no C3 C1 2.305(3) . . no C3 C7 3.556(3) . . no C4 C8 3.570(3) . . no C4 C9 3.534(3) . 2_756 no C4 C9 3.291(3) . . no C4 C2 2.310(3) . . no C4 C1 2.305(3) . . no C5 C10 3.347(3) . . no C5 C3 2.305(3) . . no C5 C5 3.597(3) . 2_766 no C5 C15 3.553(3) . 2_766 no C5 C2 2.307(3) . . no C6 C9 2.318(3) . . no C6 C11 2.589(3) . . no C6 C1 3.337(3) . . no C6 C6 3.528(3) . 2_765 no C6 C8 2.310(3) . . no C7 C3 3.556(3) . . no C7 C9 2.307(3) . . no C7 C15 3.512(3) . 2_765 no C7 C10 2.319(3) . . no C7 C2 3.280(3) . . no C8 C6 2.310(3) . . no C8 C3 3.252(3) . . no C8 C10 2.321(3) . . no C8 C4 3.570(3) . . no C8 C2 3.570(3) . . no C9 C4 3.534(3) . 2_756 no C9 O 3.026(3) . . no C9 C3 3.567(3) . . no C9 C4 3.291(3) . . no C9 C11 2.587(3) . . no C9 C6 2.318(3) . . no C9 C7 2.307(3) . . no C10 C8 2.321(3) . . no C10 C7 2.319(3) . . no C10 C5 3.347(3) . . no C11 C20 3.417(3) . . no C12 Fe 3.988(2) . . no C13 C1 3.517(3) . 2_766 no C14 C1 3.352(3) . 2_766 no C15 C5 3.553(3) . 2_766 no C15 C7 3.512(3) . 2_765 no C19 C3 3.526(3) . 1_464 no C20 C11 3.417(3) . . no C1 H16 3.05(2) . 1_655 no C1 H5 2.11(3) . . no C1 H5 2.99(3) . 2_766 no C1 H14 2.743(18) . 2_766 no C1 H2 2.13(3) . . no C1 H13 3.10(3) . 2_766 no C2 H3 2.18(3) . . no C2 H14 2.837(19) . 2_766 no C2 H1 2.14(3) . . no C3 H19 2.901(18) . 1_646 no C3 H9 3.05(3) . 2_756 no C3 H2 2.15(3) . . no C3 H4 2.14(3) . . no C4 H18' 2.836(18) . 1_646 no C4 H5 2.10(3) . . no C4 H3 2.13(3) . . no C4 H9 2.90(3) . 2_756 no C5 H5 2.93(3) . 2_766 no C5 H1 2.12(3) . . no C5 H4 2.15(3) . . no C6 H16 3.08(3) . 1_655 no C6 H7 2.14(3) . . no C6 H15 2.99(2) . . no C7 H8 2.17(3) . . no C7 H15 2.888(18) . 2_765 no C7 H6 2.11(3) . . no C8 H4 3.01(3) . 2_756 no C8 H18 3.10(2) . 1_645 no C8 H9 2.14(3) . . no C8 H7 2.14(3) . . no C9 H8 2.15(3) . . no C9 H4 2.83(3) . 2_756 no C9 H9 3.07(2) . 2_756 no C10 H6 2.12(3) . . no C10 H9 2.14(3) . . no C11 H20 2.93(2) . . no C12 H20 2.912(19) . . no C12 H9 2.98(3) . . no C15 H20 2.74(3) . . no C15 H6 3.05(3) . . no C16 H1 3.03(3) . 1_455 no H1 C16 3.03(3) . 1_655 no H1 H16 2.41(3) . 1_655 no H1 H5 2.49(4) . 2_766 no H2 O 2.58(3) . 1_655 no H2 H3 2.53(4) . 2_856 no H3 H2 2.53(4) . 2_856 no H4 C8 3.01(3) . 2_756 no H4 C9 2.83(3) . 2_756 no H4 H9 2.40(4) . 2_756 no H4 H17 2.57(4) . 2_666 no H5 C1 2.99(3) . 2_766 no H5 C5 2.93(3) . 2_766 no H5 H1 2.49(4) . 2_766 no H5 H5 2.44(4) . 2_766 no H6 C15 3.05(3) . . no H6 H16 2.47(4) . 1_655 no H7 H19 2.53(3) . 2_765 no H8 O 2.65(3) . 2_756 no H9 O 2.51(3) . . no H9 C12 2.98(3) . . no H9 Fe 3.48(3) . 2_756 no H9 C3 3.05(3) . 2_756 no H9 C4 2.90(3) . 2_756 no H9 C9 3.07(2) . 2_756 no H9 H4 2.40(4) . 2_756 no H13 H17 2.40(4) . . no H13 O 2.89(2) . 2_666 no H13 C1 3.10(3) . 2_766 no H13 H13 2.54(3) . 2_666 no H14 H18 2.40(3) . . no H14 C1 2.743(18) . 2_766 no H14 C2 2.837(19) . 2_766 no H14 H19 2.48(3) . 2_675 no H15 C6 2.99(2) . . no H15 C7 2.888(18) . 2_765 no H16 C1 3.05(2) . 1_455 no H16 C6 3.08(3) . 1_455 no H16 H1 2.41(3) . 1_455 no H16 H6 2.47(4) . 1_455 no H17 H13 2.40(4) . . no H17 H4 2.57(4) . 2_666 no H17' H20' 2.60(4) . . no H18 C8 3.10(2) . 1_465 no H18 H14 2.40(3) . . no H18' C4 2.836(18) . 1_464 no H19 C3 2.901(18) . 1_464 no H19 H7 2.53(3) . 2_765 no H19 H14 2.48(3) . 2_675 no H20 C11 2.93(2) . . no H20 C12 2.912(19) . . no H20 C15 2.74(3) . . no H20 H20 2.50(4) . 2_665 no H20' H17' 2.60(4) . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C2 H2 O 0.97(3) 2.58(3) 3.354(3) 137(2) 1_655 yes C9 H9 O 0.96(3) 2.51(3) 3.026(3) 114(2) . yes #===END of Crystallographic Information File