Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_mar357a _database_code_CSD 176563 _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Lo, Kenneth Kam-Wing' 'Lau, Jason Shing-Yip' 'Ng, Dominic Chun-Ming' 'Zhu, Nianyong' _publ_contact_author_name 'Dr Kenneth Kam-Wing Lo' _publ_contact_author_address ; Biology and Chemistry City University of Hong Kong Tat Chee Avenue Kowloon Hong Kong ; _publ_contact_author_email 'BHKENLO@CITYU.EDU.HK' _publ_section_title ; Specific labelling of sulfhydryl-containing biomolecules with redox-active N-(ferrocenyl)-iodoacetamide ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 Fe I N O' _chemical_formula_sum 'C12 H12 Fe I N O' _chemical_formula_weight 368.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'I' 'I' -0.4742 1.8119 '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' 'O' 'O' 0.0106 0.0060 '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' '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 14.041(3) _cell_length_b 9.534(2) _cell_length_c 9.553(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.47(3) _cell_angle_gamma 90.00 _cell_volume 1226.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 301(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.998 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 3.724 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 301(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5233 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 25.51 _reflns_number_total 1934 _reflns_number_gt 1397 _reflns_threshold_expression >2sigma(I) _computing_data_collection MarControl _computing_cell_refinement Scalepack _computing_data_reduction Denzo _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0390P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1934 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 I1 I 0.12582(3) 0.04479(4) 0.72270(4) 0.06184(17) Uani 1 1 d . . . Fe1 Fe 0.32959(6) -0.47560(7) 0.75077(8) 0.0484(2) Uani 1 1 d . . . O1 O 0.1024(3) -0.2825(4) 0.5561(3) 0.0665(11) Uani 1 1 d . . . N1 N 0.1352(3) -0.3488(4) 0.7925(4) 0.0438(10) Uani 1 1 d . . . C1 C 0.0945(4) -0.2622(5) 0.6798(5) 0.0469(12) Uani 1 1 d . . . C2 C 0.0373(4) -0.1411(5) 0.7137(5) 0.0516(13) Uani 1 1 d . . . H2A H 0.0237 -0.1558 0.8067 0.062 Uiso 1 1 calc R . . H2B H -0.0254 -0.1314 0.6387 0.062 Uiso 1 1 calc R . . C3 C 0.1933(4) -0.4670(5) 0.7877(5) 0.0440(12) Uani 1 1 d . . . C4 C 0.1894(5) -0.5530(5) 0.6637(6) 0.0574(14) Uani 1 1 d . . . H4 H 0.1490 -0.5389 0.5692 0.069 Uiso 1 1 calc R . . C5 C 0.2584(5) -0.6641(5) 0.7110(6) 0.0690(18) Uani 1 1 d . . . H5 H 0.2713 -0.7354 0.6526 0.083 Uiso 1 1 calc R . . C6 C 0.3039(5) -0.6475(5) 0.8618(6) 0.0653(16) Uani 1 1 d . . . H6 H 0.3516 -0.7068 0.9199 0.078 Uiso 1 1 calc R . . C7 C 0.2650(4) -0.5257(5) 0.9104(5) 0.0524(13) Uani 1 1 d . . . H7 H 0.2830 -0.4905 1.0050 0.063 Uiso 1 1 calc R . . C8 C 0.3690(5) -0.2762(6) 0.7200(6) 0.0667(16) Uani 1 1 d . . . H8 H 0.3336 -0.1958 0.7286 0.080 Uiso 1 1 calc R . . C9 C 0.3576(5) -0.3539(7) 0.5934(6) 0.0738(18) Uani 1 1 d . . . H9 H 0.3129 -0.3359 0.5028 0.089 Uiso 1 1 calc R . . C10 C 0.4266(6) -0.4651(6) 0.6277(8) 0.085(2) Uani 1 1 d . . . H10 H 0.4362 -0.5330 0.5631 0.103 Uiso 1 1 calc R . . C11 C 0.4781(5) -0.4554(6) 0.7760(8) 0.0767(18) Uani 1 1 d . . . H11 H 0.5275 -0.5158 0.8282 0.092 Uiso 1 1 calc R . . C12 C 0.4415(5) -0.3382(6) 0.8307(6) 0.0669(16) Uani 1 1 d . . . H12 H 0.4627 -0.3068 0.9267 0.080 Uiso 1 1 calc R . . H1 H 0.128(3) -0.330(4) 0.869(4) 0.025(11) Uiso 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 I1 0.0677(3) 0.0576(2) 0.0660(2) 0.00828(16) 0.02842(19) 0.00690(19) Fe1 0.0587(5) 0.0401(4) 0.0556(4) 0.0027(3) 0.0311(4) 0.0003(4) O1 0.090(4) 0.073(2) 0.0392(18) 0.0035(15) 0.0233(18) 0.012(2) N1 0.049(3) 0.054(3) 0.032(2) -0.0006(16) 0.0176(18) 0.003(2) C1 0.049(4) 0.054(3) 0.041(3) 0.001(2) 0.018(2) -0.004(3) C2 0.043(4) 0.064(3) 0.049(3) 0.006(2) 0.017(2) 0.003(3) C3 0.052(4) 0.041(3) 0.045(2) -0.0007(19) 0.024(2) -0.007(2) C4 0.069(4) 0.051(3) 0.059(3) -0.009(2) 0.029(3) -0.015(3) C5 0.100(6) 0.038(3) 0.087(4) -0.012(3) 0.055(4) -0.013(3) C6 0.083(5) 0.047(3) 0.078(4) 0.021(2) 0.043(3) 0.012(3) C7 0.063(4) 0.050(3) 0.052(3) 0.010(2) 0.028(3) 0.000(3) C8 0.067(5) 0.046(3) 0.098(4) 0.013(3) 0.042(4) 0.000(3) C9 0.083(5) 0.084(4) 0.066(3) 0.016(3) 0.039(3) -0.012(4) C10 0.108(6) 0.076(4) 0.108(6) -0.018(4) 0.090(5) -0.014(4) C11 0.060(5) 0.072(4) 0.112(5) 0.016(3) 0.048(4) 0.015(3) C12 0.062(5) 0.061(3) 0.083(4) -0.002(3) 0.031(3) -0.007(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 I1 C2 2.152(5) . ? Fe1 C12 2.022(6) . ? Fe1 C9 2.024(5) . ? Fe1 C8 2.025(5) . ? Fe1 C5 2.039(5) . ? Fe1 C10 2.039(6) . ? Fe1 C7 2.039(5) . ? Fe1 C6 2.039(5) . ? Fe1 C11 2.039(7) . ? Fe1 C3 2.043(5) . ? Fe1 C4 2.045(6) . ? O1 C1 1.234(5) . ? N1 C1 1.348(6) . ? N1 C3 1.400(6) . ? C1 C2 1.494(7) . ? C3 C7 1.426(7) . ? C3 C4 1.429(6) . ? C4 C5 1.419(8) . ? C5 C6 1.409(7) . ? C6 C7 1.415(7) . ? C8 C12 1.376(8) . ? C8 C9 1.388(7) . ? C9 C10 1.411(9) . ? C10 C11 1.399(10) . ? C11 C12 1.392(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 C12 Fe1 C9 67.3(2) . . ? C12 Fe1 C8 39.8(2) . . ? C9 Fe1 C8 40.1(2) . . ? C12 Fe1 C5 158.3(3) . . ? C9 Fe1 C5 123.7(2) . . ? C8 Fe1 C5 160.1(3) . . ? C12 Fe1 C10 67.1(3) . . ? C9 Fe1 C10 40.6(3) . . ? C8 Fe1 C10 67.4(2) . . ? C5 Fe1 C10 108.0(2) . . ? C12 Fe1 C7 109.4(2) . . ? C9 Fe1 C7 155.6(2) . . ? C8 Fe1 C7 121.8(2) . . ? C5 Fe1 C7 68.5(2) . . ? C10 Fe1 C7 162.6(3) . . ? C12 Fe1 C6 123.9(3) . . ? C9 Fe1 C6 161.4(2) . . ? C8 Fe1 C6 157.8(2) . . ? C5 Fe1 C6 40.4(2) . . ? C10 Fe1 C6 125.8(3) . . ? C7 Fe1 C6 40.61(19) . . ? C12 Fe1 C11 40.1(2) . . ? C9 Fe1 C11 68.0(3) . . ? C8 Fe1 C11 67.4(2) . . ? C5 Fe1 C11 122.4(3) . . ? C10 Fe1 C11 40.1(3) . . ? C7 Fe1 C11 126.2(3) . . ? C6 Fe1 C11 109.9(3) . . ? C12 Fe1 C3 125.1(2) . . ? C9 Fe1 C3 119.6(2) . . ? C8 Fe1 C3 107.2(2) . . ? C5 Fe1 C3 68.5(2) . . ? C10 Fe1 C3 155.4(3) . . ? C7 Fe1 C3 40.9(2) . . ? C6 Fe1 C3 68.3(2) . . ? C11 Fe1 C3 162.2(2) . . ? C12 Fe1 C4 160.5(2) . . ? C9 Fe1 C4 105.8(2) . . ? C8 Fe1 C4 123.4(2) . . ? C5 Fe1 C4 40.7(2) . . ? C10 Fe1 C4 120.4(3) . . ? C7 Fe1 C4 68.8(2) . . ? C6 Fe1 C4 68.3(2) . . ? C11 Fe1 C4 156.4(2) . . ? C3 Fe1 C4 40.91(19) . . ? C1 N1 C3 125.8(4) . . ? O1 C1 N1 122.5(4) . . ? O1 C1 C2 121.9(4) . . ? N1 C1 C2 115.6(4) . . ? C1 C2 I1 107.8(4) . . ? N1 C3 C7 124.9(4) . . ? N1 C3 C4 127.2(4) . . ? C7 C3 C4 107.9(4) . . ? N1 C3 Fe1 128.4(3) . . ? C7 C3 Fe1 69.4(3) . . ? C4 C3 Fe1 69.6(3) . . ? C5 C4 C3 107.6(5) . . ? C5 C4 Fe1 69.4(4) . . ? C3 C4 Fe1 69.5(3) . . ? C6 C5 C4 108.2(5) . . ? C6 C5 Fe1 69.8(3) . . ? C4 C5 Fe1 69.9(3) . . ? C5 C6 C7 108.8(5) . . ? C5 C6 Fe1 69.8(3) . . ? C7 C6 Fe1 69.7(3) . . ? C6 C7 C3 107.5(4) . . ? C6 C7 Fe1 69.7(3) . . ? C3 C7 Fe1 69.7(3) . . ? C12 C8 C9 108.5(6) . . ? C12 C8 Fe1 70.0(3) . . ? C9 C8 Fe1 69.9(3) . . ? C8 C9 C10 107.3(6) . . ? C8 C9 Fe1 70.0(3) . . ? C10 C9 Fe1 70.2(3) . . ? C11 C10 C9 108.0(5) . . ? C11 C10 Fe1 70.0(3) . . ? C9 C10 Fe1 69.1(3) . . ? C12 C11 C10 107.1(6) . . ? C12 C11 Fe1 69.3(4) . . ? C10 C11 Fe1 69.9(4) . . ? C8 C12 C11 109.1(6) . . ? C8 C12 Fe1 70.2(4) . . ? C11 C12 Fe1 70.6(4) . . ? _diffrn_measured_fraction_theta_max 0.844 _diffrn_reflns_theta_full 25.51 _diffrn_measured_fraction_theta_full 0.844 _refine_diff_density_max 0.582 _refine_diff_density_min -1.169 _refine_diff_density_rms 0.153