# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Kaifer, A.' 'Captain, Burjor' 'Song Yi.' _publ_contact_author_name 'Kaifer, A.' _publ_contact_author_email akaifer@miami.edu _publ_section_title ; The importance of methylation in the binding of (ferrocenylmethyl)- tempammonium guests by cucurbit[n]uril (n = 7, 8) hosts ; # Attachment 'Complex 1.cif' data_collect_0m _database_code_depnum_ccdc_archive 'CCDC 815163' #TrackingRef 'Complex 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H29 Fe N2 O' _chemical_formula_weight 369.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' 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 P2(1)/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 13.9513(7) _cell_length_b 5.9462(3) _cell_length_c 22.6371(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.1085(7) _cell_angle_gamma 90.00 _cell_volume 1848.76(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7227 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 28.74 _exptl_crystal_description Bar _exptl_crystal_colour Orange _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 0.824 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7447 _exptl_absorpt_correction_T_max 0.9678 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16569 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4043 _reflns_number_gt 3428 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0394P)^2^+2.4297P] 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 4043 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.180 _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 0.22427(3) 0.11741(8) 0.335953(19) 0.04004(15) Uani 1 1 d . A 1 O1 O 0.24522(19) 1.1216(5) 0.02389(12) 0.0683(8) Uani 1 1 d . A 1 N1 N 0.3374(5) 0.5330(10) 0.2124(2) 0.0434(12) Uani 0.50 1 d P A 1 H1 H 0.3908 0.5821 0.2333 0.052 Uiso 0.50 1 calc PR A 1 N2 N 0.2586(2) 0.9786(5) 0.06693(11) 0.0445(6) Uani 1 1 d . A 1 C1 C 0.3256(3) 0.2599(6) 0.29157(15) 0.0563(9) Uani 1 1 d . A 1 C2 C 0.3151(3) 0.3884(6) 0.34338(15) 0.0525(8) Uani 1 1 d . A 1 H2 H 0.2968 0.5387 0.3437 0.063 Uiso 1 1 calc R A 1 C3 C 0.3374(2) 0.2466(6) 0.39399(14) 0.0482(8) Uani 1 1 d . A 1 H3 H 0.3363 0.2869 0.4336 0.058 Uiso 1 1 calc R A 1 C4 C 0.3619(2) 0.0327(6) 0.37389(15) 0.0486(8) Uani 1 1 d . A 1 H4 H 0.3801 -0.0921 0.3980 0.058 Uiso 1 1 calc R A 1 C5 C 0.3539(3) 0.0408(6) 0.31105(15) 0.0481(8) Uani 1 1 d . A 1 H5 H 0.3654 -0.0783 0.2866 0.058 Uiso 1 1 calc R A 1 C6 C 0.0924(3) 0.0967(8) 0.2802(2) 0.0722(12) Uani 1 1 d . A 1 H6 H 0.0785 0.1398 0.2401 0.087 Uiso 1 1 calc R A 1 C7 C 0.0866(3) 0.2349(8) 0.3294(2) 0.0760(13) Uani 1 1 d . A 1 H7 H 0.0685 0.3856 0.3278 0.091 Uiso 1 1 calc R A 1 C8 C 0.1129(3) 0.1057(8) 0.3819(2) 0.0700(12) Uani 1 1 d . A 1 H8 H 0.1155 0.1558 0.4210 0.084 Uiso 1 1 calc R A 1 C9 C 0.1347(3) -0.1139(7) 0.3643(2) 0.0649(10) Uani 1 1 d . A 1 H9 H 0.1537 -0.2346 0.3898 0.078 Uiso 1 1 calc R A 1 C10 C 0.1226(3) -0.1165(7) 0.3014(2) 0.0667(11) Uani 1 1 d . A 1 H10 H 0.1330 -0.2394 0.2779 0.080 Uiso 1 1 calc R A 1 C11 C 0.2768(7) 0.3535(13) 0.2272(3) 0.0504(17) Uani 0.50 1 d P A 1 H11A H 0.2723 0.2350 0.1974 0.061 Uiso 0.50 1 calc PR A 1 H11B H 0.2117 0.4088 0.2283 0.061 Uiso 0.50 1 calc PR A 1 C12 C 0.2866(4) 0.6155(6) 0.15223(15) 0.0778(15) Uani 1 1 d . A 1 H12 H 0.2773 0.5049 0.1268 0.093 Uiso 1 1 d . B 1 C13 C 0.3703(4) 0.7598(7) 0.14197(18) 0.0761(14) Uani 1 1 d . A 1 H13A H 0.4282 0.6667 0.1465 0.091 Uiso 1 1 calc R A 1 H13B H 0.3813 0.8735 0.1732 0.091 Uiso 1 1 calc R A 1 C14 C 0.3583(3) 0.8783(6) 0.08096(17) 0.0559(9) Uani 1 1 d . A 1 C15 C 0.1696(3) 0.8743(6) 0.08302(15) 0.0498(8) Uani 1 1 d . A 1 C16 C 0.1949(4) 0.7606(6) 0.14435(16) 0.0659(11) Uani 1 1 d . A 1 H16A H 0.2034 0.8758 0.1752 0.079 Uiso 1 1 calc R A 1 H16B H 0.1405 0.6672 0.1504 0.079 Uiso 1 1 calc R A 1 C17 C 0.4307(3) 1.0707(8) 0.0836(3) 0.0805(14) Uani 1 1 d . A 1 H17A H 0.4237 1.1415 0.0450 0.121 Uiso 1 1 calc R A 1 H17B H 0.4957 1.0133 0.0947 0.121 Uiso 1 1 calc R A 1 H17C H 0.4184 1.1788 0.1129 0.121 Uiso 1 1 calc R A 1 C18 C 0.3713(3) 0.7135(8) 0.03100(19) 0.0716(12) Uani 1 1 d . A 1 H18A H 0.3332 0.5809 0.0341 0.107 Uiso 1 1 calc R A 1 H18B H 0.4387 0.6732 0.0349 0.107 Uiso 1 1 calc R A 1 H18C H 0.3501 0.7833 -0.0073 0.107 Uiso 1 1 calc R A 1 C19 C 0.0969(3) 1.0647(7) 0.0860(2) 0.0685(11) Uani 1 1 d . A 1 H19A H 0.1244 1.1711 0.1161 0.103 Uiso 1 1 calc R A 1 H19B H 0.0380 1.0039 0.0959 0.103 Uiso 1 1 calc R A 1 H19C H 0.0826 1.1385 0.0477 0.103 Uiso 1 1 calc R A 1 C20 C 0.1270(3) 0.7054(8) 0.03415(19) 0.0691(11) Uani 1 1 d . A 1 H20A H 0.1191 0.7770 -0.0044 0.104 Uiso 1 1 calc R A 1 H20B H 0.0648 0.6539 0.0414 0.104 Uiso 1 1 calc R A 1 H20C H 0.1703 0.5797 0.0349 0.104 Uiso 1 1 calc R A 1 N1D N 0.2730(5) 0.5223(9) 0.2146(2) 0.0397(12) Uani 0.50 1 d P A 1 H1D H 0.2323 0.5714 0.2360 0.048 Uiso 0.50 1 calc PR A 1 C11D C 0.3416(6) 0.3366(11) 0.2303(3) 0.0405(14) Uani 0.50 1 d P A 1 H11C H 0.4081 0.3872 0.2319 0.049 Uiso 0.50 1 calc PR A 1 H11D H 0.3283 0.2155 0.2013 0.049 Uiso 0.50 1 calc PR A 1 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 0.0421(2) 0.0368(2) 0.0394(2) -0.00135(19) 0.00197(17) 0.0025(2) O1 0.0595(15) 0.0782(19) 0.0697(17) 0.0446(15) 0.0180(13) 0.0137(14) N1 0.055(4) 0.042(3) 0.033(3) 0.008(2) 0.007(3) -0.008(3) N2 0.0492(15) 0.0451(15) 0.0394(13) 0.0128(12) 0.0084(11) 0.0065(12) C1 0.092(3) 0.0397(18) 0.0379(17) 0.0051(14) 0.0136(17) -0.0158(18) C2 0.071(2) 0.0377(17) 0.0465(18) -0.0008(15) 0.0030(16) -0.0085(16) C3 0.0509(19) 0.061(2) 0.0306(14) -0.0023(14) 0.0015(13) -0.0109(16) C4 0.0454(18) 0.055(2) 0.0436(17) 0.0144(15) 0.0027(14) 0.0040(15) C5 0.0545(19) 0.0461(18) 0.0481(18) 0.0037(15) 0.0216(15) -0.0016(15) C6 0.048(2) 0.082(3) 0.077(3) -0.003(2) -0.0146(19) 0.003(2) C7 0.041(2) 0.067(3) 0.116(4) -0.009(3) 0.006(2) 0.0143(19) C8 0.053(2) 0.077(3) 0.085(3) -0.019(2) 0.026(2) -0.002(2) C9 0.056(2) 0.061(2) 0.081(3) -0.001(2) 0.021(2) -0.0112(19) C10 0.055(2) 0.062(2) 0.081(3) -0.018(2) 0.0051(19) -0.0131(19) C11 0.071(5) 0.043(4) 0.034(3) 0.007(3) 0.002(3) -0.012(4) C12 0.170(5) 0.0301(17) 0.0294(16) 0.0042(14) 0.006(2) 0.015(2) C13 0.114(4) 0.048(2) 0.054(2) -0.0070(18) -0.023(2) 0.034(2) C14 0.057(2) 0.052(2) 0.056(2) 0.0004(17) 0.0020(16) 0.0162(18) C15 0.062(2) 0.0447(18) 0.0453(17) 0.0074(15) 0.0166(15) -0.0002(16) C16 0.120(4) 0.0391(19) 0.0461(19) 0.0054(16) 0.034(2) -0.001(2) C17 0.051(2) 0.071(3) 0.117(4) -0.010(3) 0.007(2) 0.007(2) C18 0.075(3) 0.075(3) 0.069(3) -0.008(2) 0.023(2) 0.019(2) C19 0.059(2) 0.063(3) 0.090(3) 0.015(2) 0.031(2) 0.0057(19) C20 0.074(3) 0.070(3) 0.062(2) 0.000(2) 0.005(2) -0.008(2) N1D 0.056(4) 0.034(3) 0.034(3) 0.010(2) 0.021(3) 0.009(3) C11D 0.043(4) 0.040(4) 0.042(3) 0.010(3) 0.014(3) 0.010(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 C8 2.017(4) . ? Fe1 C3 2.020(3) . ? Fe1 C4 2.024(3) . ? Fe1 C7 2.025(4) . ? Fe1 C9 2.036(4) . ? Fe1 C2 2.038(3) . ? Fe1 C5 2.039(3) . ? Fe1 C10 2.042(4) . ? Fe1 C6 2.044(4) . ? Fe1 C1 2.056(4) . ? O1 N2 1.282(3) . ? N1 C11 1.437(9) . ? N1 C12 1.504(6) . ? N2 C15 1.490(4) . ? N2 C14 1.496(4) . ? C1 C5 1.410(5) . ? C1 C2 1.429(5) . ? C1 C11D 1.513(7) . ? C1 C11 1.597(8) . ? C2 C3 1.413(5) . ? C3 C4 1.412(5) . ? C4 C5 1.408(5) . ? C6 C10 1.395(6) . ? C6 C7 1.398(6) . ? C7 C8 1.408(7) . ? C8 C9 1.413(6) . ? C9 C10 1.405(6) . ? C12 C13 1.499(7) . ? C12 C16 1.528(6) . ? C12 N1D 1.558(6) . ? C13 C14 1.533(5) . ? C14 C17 1.520(6) . ? C14 C18 1.531(5) . ? C15 C16 1.529(5) . ? C15 C19 1.529(5) . ? C15 C20 1.534(5) . ? N1D C11D 1.464(8) . ? 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 C8 Fe1 C3 105.25(16) . . ? C8 Fe1 C4 122.13(17) . . ? C3 Fe1 C4 40.88(15) . . ? C8 Fe1 C7 40.77(19) . . ? C3 Fe1 C7 122.65(18) . . ? C4 Fe1 C7 159.02(18) . . ? C8 Fe1 C9 40.81(17) . . ? C3 Fe1 C9 120.28(16) . . ? C4 Fe1 C9 106.66(16) . . ? C7 Fe1 C9 68.25(19) . . ? C8 Fe1 C2 120.60(17) . . ? C3 Fe1 C2 40.73(14) . . ? C4 Fe1 C2 68.41(15) . . ? C7 Fe1 C2 107.55(18) . . ? C9 Fe1 C2 156.17(16) . . ? C8 Fe1 C5 159.42(17) . . ? C3 Fe1 C5 68.57(14) . . ? C4 Fe1 C5 40.55(13) . . ? C7 Fe1 C5 158.97(19) . . ? C9 Fe1 C5 124.02(16) . . ? C2 Fe1 C5 68.31(15) . . ? C8 Fe1 C10 68.14(18) . . ? C3 Fe1 C10 156.82(17) . . ? C4 Fe1 C10 122.43(17) . . ? C7 Fe1 C10 67.72(19) . . ? C9 Fe1 C10 40.31(17) . . ? C2 Fe1 C10 161.81(17) . . ? C5 Fe1 C10 109.40(16) . . ? C8 Fe1 C6 68.0(2) . . ? C3 Fe1 C6 160.15(17) . . ? C4 Fe1 C6 158.56(18) . . ? C7 Fe1 C6 40.19(18) . . ? C9 Fe1 C6 67.59(19) . . ? C2 Fe1 C6 125.28(17) . . ? C5 Fe1 C6 124.19(17) . . ? C10 Fe1 C6 39.92(18) . . ? C8 Fe1 C1 157.61(17) . . ? C3 Fe1 C1 68.59(14) . . ? C4 Fe1 C1 68.12(14) . . ? C7 Fe1 C1 123.18(19) . . ? C9 Fe1 C1 160.96(16) . . ? C2 Fe1 C1 40.84(14) . . ? C5 Fe1 C1 40.27(14) . . ? C10 Fe1 C1 125.78(17) . . ? C6 Fe1 C1 110.17(18) . . ? C11 N1 C12 104.5(6) . . ? O1 N2 C15 116.5(3) . . ? O1 N2 C14 115.6(3) . . ? C15 N2 C14 124.5(3) . . ? C5 C1 C2 107.5(3) . . ? C5 C1 C11D 119.1(4) . . ? C2 C1 C11D 130.1(4) . . ? C5 C1 C11 131.2(4) . . ? C2 C1 C11 118.3(4) . . ? C11D C1 C11 33.5(3) . . ? C5 C1 Fe1 69.21(19) . . ? C2 C1 Fe1 68.9(2) . . ? C11D C1 Fe1 142.8(4) . . ? C11 C1 Fe1 111.7(4) . . ? C3 C2 C1 107.9(3) . . ? C3 C2 Fe1 68.93(19) . . ? C1 C2 Fe1 70.2(2) . . ? C4 C3 C2 107.9(3) . . ? C4 C3 Fe1 69.73(19) . . ? C2 C3 Fe1 70.33(19) . . ? C5 C4 C3 108.3(3) . . ? C5 C4 Fe1 70.26(19) . . ? C3 C4 Fe1 69.39(19) . . ? C4 C5 C1 108.4(3) . . ? C4 C5 Fe1 69.19(19) . . ? C1 C5 Fe1 70.5(2) . . ? C10 C6 C7 108.4(4) . . ? C10 C6 Fe1 69.9(2) . . ? C7 C6 Fe1 69.2(2) . . ? C6 C7 C8 108.0(4) . . ? C6 C7 Fe1 70.6(2) . . ? C8 C7 Fe1 69.3(2) . . ? C7 C8 C9 107.7(4) . . ? C7 C8 Fe1 69.9(2) . . ? C9 C8 Fe1 70.3(2) . . ? C10 C9 C8 107.6(4) . . ? C10 C9 Fe1 70.1(2) . . ? C8 C9 Fe1 68.8(2) . . ? C6 C10 C9 108.3(4) . . ? C6 C10 Fe1 70.1(2) . . ? C9 C10 Fe1 69.6(2) . . ? N1 C11 C1 107.2(6) . . ? C13 C12 N1 94.1(4) . . ? C13 C12 C16 108.5(3) . . ? N1 C12 C16 122.8(4) . . ? C13 C12 N1D 124.5(4) . . ? N1 C12 N1D 34.5(3) . . ? C16 C12 N1D 94.2(4) . . ? C12 C13 C14 116.0(3) . . ? N2 C14 C17 107.2(3) . . ? N2 C14 C18 109.0(3) . . ? C17 C14 C18 110.3(4) . . ? N2 C14 C13 108.9(3) . . ? C17 C14 C13 110.1(4) . . ? C18 C14 C13 111.3(3) . . ? N2 C15 C16 109.7(3) . . ? N2 C15 C19 106.9(3) . . ? C16 C15 C19 109.7(3) . . ? N2 C15 C20 109.3(3) . . ? C16 C15 C20 111.3(3) . . ? C19 C15 C20 109.9(3) . . ? C12 C16 C15 114.3(3) . . ? C11D N1D C12 108.1(5) . . ? N1D C11D C1 104.8(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.340 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.060 # Attachment 'Complex 2.cif' data_collect_0m2 _database_code_depnum_ccdc_archive 'CCDC 815164' #TrackingRef 'Complex 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H31 Fe N2 O' _chemical_formula_weight 383.33 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' 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 P2(1)/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 11.6659(5) _cell_length_b 5.9289(2) _cell_length_c 28.2755(12) _cell_angle_alpha 90.00 _cell_angle_beta 99.3020(6) _cell_angle_gamma 90.00 _cell_volume 1929.98(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9223 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 31.68 _exptl_crystal_description Bar _exptl_crystal_colour Orange _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 0.792 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7023 _exptl_absorpt_correction_T_max 0.9250 _exptl_absorpt_process_details '(SADABS 2007/4 Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20035 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 29.00 _reflns_number_total 5096 _reflns_number_gt 4538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0485P)^2^+0.5466P] 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 5096 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 0.682527(17) 1.20513(4) 0.103629(7) 0.03109(8) Uani 1 1 d . . . O1 O 0.04827(13) 0.2329(3) 0.11748(5) 0.0577(4) Uani 1 1 d . . . N1 N 0.42511(10) 0.8054(2) 0.16729(4) 0.0304(2) Uani 1 1 d . . . N2 N 0.12999(11) 0.3769(2) 0.12832(4) 0.0348(3) Uani 1 1 d . . . C1 C 0.58209(13) 1.0505(3) 0.14693(5) 0.0345(3) Uani 1 1 d . . . C2 C 0.68673(14) 0.9288(3) 0.14697(6) 0.0402(3) Uani 1 1 d . . . H2 H 0.6923 0.7790 0.1378 0.048 Uiso 1 1 calc R . . C3 C 0.78175(14) 1.0746(3) 0.16334(6) 0.0435(4) Uani 1 1 d . . . H3 H 0.8601 1.0373 0.1665 0.052 Uiso 1 1 calc R . . C4 C 0.73615(15) 1.2851(3) 0.17384(6) 0.0414(4) Uani 1 1 d . . . H4 H 0.7793 1.4111 0.1854 0.050 Uiso 1 1 calc R . . C5 C 0.61269(15) 1.2725(3) 0.16377(6) 0.0365(3) Uani 1 1 d . . . H5 H 0.5612 1.3885 0.1675 0.044 Uiso 1 1 calc R . . C6 C 0.58827(19) 1.2322(4) 0.03640(7) 0.0522(5) Uani 1 1 d . . . H6 H 0.5114 1.1879 0.0272 0.063 Uiso 1 1 calc R . . C7 C 0.6871(2) 1.0969(4) 0.03559(6) 0.0550(5) Uani 1 1 d . . . H7 H 0.6870 0.9475 0.0256 0.066 Uiso 1 1 calc R . . C8 C 0.78672(18) 1.2275(4) 0.05265(7) 0.0540(5) Uani 1 1 d . . . H8 H 0.8635 1.1793 0.0560 0.065 Uiso 1 1 calc R . . C9 C 0.74871(18) 1.4431(4) 0.06363(6) 0.0518(5) Uani 1 1 d . . . H9 H 0.7962 1.5629 0.0755 0.062 Uiso 1 1 calc R . . C10 C 0.62686(18) 1.4472(3) 0.05365(6) 0.0509(4) Uani 1 1 d . . . H10 H 0.5798 1.5700 0.0577 0.061 Uiso 1 1 calc R . . C11 C 0.46116(13) 0.9607(3) 0.13187(6) 0.0404(4) Uani 1 1 d . . . H11A H 0.4072 1.0862 0.1270 0.048 Uiso 1 1 calc R . . H11B H 0.4574 0.8825 0.1015 0.048 Uiso 1 1 calc R . . C12 C 0.44111(15) 0.9148(3) 0.21416(6) 0.0420(4) Uani 1 1 d . . . H12A H 0.5214 0.9543 0.2235 0.063 Uiso 1 1 calc R . . H12B H 0.4181 0.8134 0.2374 0.063 Uiso 1 1 calc R . . H12C H 0.3944 1.0488 0.2124 0.063 Uiso 1 1 calc R . . C13 C 0.30316(12) 0.7299(2) 0.15193(5) 0.0284(3) Uani 1 1 d . . . H13 H 0.2516 0.8612 0.1471 0.034 Uiso 1 1 calc R . . C14 C 0.26619(13) 0.5755(3) 0.18983(5) 0.0342(3) Uani 1 1 d . . . H14A H 0.2704 0.6600 0.2194 0.041 Uiso 1 1 calc R . . H14B H 0.3214 0.4525 0.1957 0.041 Uiso 1 1 calc R . . C15 C 0.14418(13) 0.4758(3) 0.17714(5) 0.0353(3) Uani 1 1 d . . . C16 C 0.17420(13) 0.4896(3) 0.08754(5) 0.0335(3) Uani 1 1 d . . . C17 C 0.29364(12) 0.5949(3) 0.10539(5) 0.0322(3) Uani 1 1 d . . . H17A H 0.3510 0.4750 0.1100 0.039 Uiso 1 1 calc R . . H17B H 0.3133 0.6935 0.0805 0.039 Uiso 1 1 calc R . . C18 C 0.04938(17) 0.6530(4) 0.17963(8) 0.0557(5) Uani 1 1 d . . . H18A H 0.0642 0.7835 0.1614 0.083 Uiso 1 1 calc R . . H18B H 0.0497 0.6955 0.2124 0.083 Uiso 1 1 calc R . . H18C H -0.0250 0.5909 0.1666 0.083 Uiso 1 1 calc R . . C19 C 0.13089(19) 0.2850(3) 0.21231(7) 0.0511(5) Uani 1 1 d . . . H19A H 0.0528 0.2283 0.2061 0.077 Uiso 1 1 calc R . . H19B H 0.1474 0.3414 0.2445 0.077 Uiso 1 1 calc R . . H19C H 0.1841 0.1657 0.2083 0.077 Uiso 1 1 calc R . . C20 C 0.08668(16) 0.6659(3) 0.06429(7) 0.0478(4) Uani 1 1 d . . . H20A H 0.0110 0.5986 0.0571 0.072 Uiso 1 1 calc R . . H20B H 0.1098 0.7195 0.0352 0.072 Uiso 1 1 calc R . . H20C H 0.0844 0.7899 0.0860 0.072 Uiso 1 1 calc R . . C21 C 0.18804(18) 0.3080(3) 0.05051(6) 0.0469(4) Uani 1 1 d . . . H21A H 0.2347 0.1870 0.0658 0.070 Uiso 1 1 calc R . . H21B H 0.2252 0.3718 0.0257 0.070 Uiso 1 1 calc R . . H21C H 0.1129 0.2512 0.0368 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 Fe1 0.02900(12) 0.03450(13) 0.02964(12) 0.00306(8) 0.00431(8) -0.00670(8) O1 0.0585(8) 0.0641(9) 0.0499(7) -0.0062(6) 0.0068(6) -0.0382(7) N1 0.0273(6) 0.0314(6) 0.0323(6) 0.0032(5) 0.0041(4) -0.0064(5) N2 0.0342(6) 0.0350(7) 0.0350(6) -0.0005(5) 0.0053(5) -0.0109(5) C1 0.0322(7) 0.0386(8) 0.0327(7) 0.0046(6) 0.0054(5) -0.0097(6) C2 0.0425(8) 0.0359(8) 0.0425(8) 0.0087(7) 0.0075(6) -0.0015(7) C3 0.0317(7) 0.0564(10) 0.0409(8) 0.0126(8) 0.0009(6) -0.0019(7) C4 0.0408(8) 0.0483(9) 0.0338(8) 0.0021(7) 0.0016(6) -0.0177(7) C5 0.0386(8) 0.0380(8) 0.0341(7) 0.0012(6) 0.0090(6) -0.0055(6) C6 0.0518(10) 0.0644(12) 0.0364(9) 0.0060(8) -0.0054(7) -0.0143(9) C7 0.0801(14) 0.0513(11) 0.0348(8) -0.0033(8) 0.0132(8) -0.0054(10) C8 0.0482(10) 0.0773(14) 0.0398(9) 0.0082(9) 0.0176(8) -0.0009(9) C9 0.0619(11) 0.0549(11) 0.0396(9) 0.0087(8) 0.0114(8) -0.0249(9) C10 0.0653(12) 0.0467(10) 0.0395(9) 0.0138(8) 0.0046(8) 0.0024(9) C11 0.0345(7) 0.0480(9) 0.0376(8) 0.0110(7) 0.0025(6) -0.0148(7) C12 0.0411(8) 0.0479(10) 0.0358(8) -0.0020(7) 0.0031(6) -0.0146(7) C13 0.0261(6) 0.0277(6) 0.0315(7) 0.0003(5) 0.0048(5) -0.0045(5) C14 0.0351(7) 0.0377(8) 0.0305(7) 0.0000(6) 0.0072(5) -0.0112(6) C15 0.0344(7) 0.0369(8) 0.0365(7) -0.0031(6) 0.0120(6) -0.0100(6) C16 0.0336(7) 0.0360(8) 0.0304(7) 0.0015(6) 0.0032(5) -0.0072(6) C17 0.0302(7) 0.0369(8) 0.0304(7) -0.0003(6) 0.0071(5) -0.0066(6) C18 0.0428(9) 0.0559(11) 0.0742(13) -0.0112(10) 0.0273(9) -0.0035(8) C19 0.0623(12) 0.0542(11) 0.0396(9) 0.0012(8) 0.0166(8) -0.0264(9) C20 0.0425(9) 0.0499(10) 0.0475(9) 0.0105(8) -0.0029(7) -0.0016(8) C21 0.0591(11) 0.0466(10) 0.0345(8) -0.0069(7) 0.0061(7) -0.0110(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C8 2.0346(18) . ? Fe1 C9 2.0367(17) . ? Fe1 C7 2.0369(18) . ? Fe1 C4 2.0388(16) . ? Fe1 C3 2.0391(16) . ? Fe1 C5 2.0405(16) . ? Fe1 C2 2.0420(16) . ? Fe1 C6 2.0427(18) . ? Fe1 C1 2.0434(14) . ? Fe1 C10 2.0451(18) . ? O1 N2 1.2796(17) . ? N1 C12 1.460(2) . ? N1 C11 1.4708(19) . ? N1 C13 1.4877(17) . ? N2 C15 1.4843(19) . ? N2 C16 1.4946(19) . ? C1 C2 1.418(2) . ? C1 C5 1.425(2) . ? C1 C11 1.504(2) . ? C2 C3 1.423(2) . ? C3 C4 1.407(3) . ? C4 C5 1.424(2) . ? C6 C7 1.408(3) . ? C6 C10 1.412(3) . ? C7 C8 1.415(3) . ? C8 C9 1.404(3) . ? C9 C10 1.404(3) . ? C13 C14 1.5234(19) . ? C13 C17 1.529(2) . ? C14 C15 1.530(2) . ? C15 C19 1.530(2) . ? C15 C18 1.535(2) . ? C16 C21 1.529(2) . ? C16 C20 1.533(2) . ? C16 C17 1.5357(19) . ? 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 C8 Fe1 C9 40.34(9) . . ? C8 Fe1 C7 40.66(9) . . ? C9 Fe1 C7 67.88(8) . . ? C8 Fe1 C4 123.39(8) . . ? C9 Fe1 C4 107.18(7) . . ? C7 Fe1 C4 160.44(9) . . ? C8 Fe1 C3 106.69(8) . . ? C9 Fe1 C3 120.49(7) . . ? C7 Fe1 C3 124.37(8) . . ? C4 Fe1 C3 40.38(8) . . ? C8 Fe1 C5 160.47(8) . . ? C9 Fe1 C5 124.43(8) . . ? C7 Fe1 C5 157.50(8) . . ? C4 Fe1 C5 40.87(7) . . ? C3 Fe1 C5 68.53(7) . . ? C8 Fe1 C2 121.23(8) . . ? C9 Fe1 C2 156.16(8) . . ? C7 Fe1 C2 108.21(8) . . ? C4 Fe1 C2 68.19(7) . . ? C3 Fe1 C2 40.81(7) . . ? C5 Fe1 C2 68.35(7) . . ? C8 Fe1 C6 68.22(9) . . ? C9 Fe1 C6 67.92(8) . . ? C7 Fe1 C6 40.37(9) . . ? C4 Fe1 C6 157.25(9) . . ? C3 Fe1 C6 161.53(8) . . ? C5 Fe1 C6 122.20(8) . . ? C2 Fe1 C6 125.35(8) . . ? C8 Fe1 C1 156.91(8) . . ? C9 Fe1 C1 161.62(8) . . ? C7 Fe1 C1 121.99(8) . . ? C4 Fe1 C1 68.67(6) . . ? C3 Fe1 C1 68.74(6) . . ? C5 Fe1 C1 40.85(6) . . ? C2 Fe1 C1 40.62(6) . . ? C6 Fe1 C1 108.56(7) . . ? C8 Fe1 C10 67.91(9) . . ? C9 Fe1 C10 40.24(8) . . ? C7 Fe1 C10 67.80(9) . . ? C4 Fe1 C10 121.52(8) . . ? C3 Fe1 C10 155.92(8) . . ? C5 Fe1 C10 108.27(8) . . ? C2 Fe1 C10 162.19(8) . . ? C6 Fe1 C10 40.43(8) . . ? C1 Fe1 C10 125.46(7) . . ? C12 N1 C11 109.34(13) . . ? C12 N1 C13 112.00(12) . . ? C11 N1 C13 110.79(11) . . ? O1 N2 C15 116.94(12) . . ? O1 N2 C16 116.76(12) . . ? C15 N2 C16 122.70(12) . . ? C2 C1 C5 107.51(14) . . ? C2 C1 C11 126.01(15) . . ? C5 C1 C11 126.47(15) . . ? C2 C1 Fe1 69.64(9) . . ? C5 C1 Fe1 69.46(9) . . ? C11 C1 Fe1 126.28(10) . . ? C1 C2 C3 108.43(15) . . ? C1 C2 Fe1 69.74(9) . . ? C3 C2 Fe1 69.49(9) . . ? C4 C3 C2 107.84(15) . . ? C4 C3 Fe1 69.79(9) . . ? C2 C3 Fe1 69.70(9) . . ? C3 C4 C5 108.41(15) . . ? C3 C4 Fe1 69.82(10) . . ? C5 C4 Fe1 69.63(9) . . ? C4 C5 C1 107.80(15) . . ? C4 C5 Fe1 69.50(9) . . ? C1 C5 Fe1 69.68(9) . . ? C7 C6 C10 107.67(18) . . ? C7 C6 Fe1 69.60(11) . . ? C10 C6 Fe1 69.88(10) . . ? C6 C7 C8 108.21(19) . . ? C6 C7 Fe1 70.03(11) . . ? C8 C7 Fe1 69.58(11) . . ? C9 C8 C7 107.59(18) . . ? C9 C8 Fe1 69.91(10) . . ? C7 C8 Fe1 69.76(11) . . ? C8 C9 C10 108.49(18) . . ? C8 C9 Fe1 69.75(11) . . ? C10 C9 Fe1 70.20(10) . . ? C9 C10 C6 108.03(19) . . ? C9 C10 Fe1 69.56(10) . . ? C6 C10 Fe1 69.69(11) . . ? N1 C11 C1 112.79(12) . . ? N1 C13 C14 109.98(11) . . ? N1 C13 C17 109.98(11) . . ? C14 C13 C17 107.56(12) . . ? C13 C14 C15 115.19(12) . . ? N2 C15 C14 109.30(11) . . ? N2 C15 C19 107.74(13) . . ? C14 C15 C19 108.75(14) . . ? N2 C15 C18 109.89(14) . . ? C14 C15 C18 112.00(14) . . ? C19 C15 C18 109.06(15) . . ? N2 C16 C21 107.53(13) . . ? N2 C16 C20 110.29(13) . . ? C21 C16 C20 108.85(14) . . ? N2 C16 C17 109.64(11) . . ? C21 C16 C17 108.70(13) . . ? C20 C16 C17 111.72(13) . . ? C13 C17 C16 115.55(12) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.495 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.061