# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name M.-C.Cassani L.Busetto B.Ballarin A.M.Ferrari I.Miletto C.Femoni G.Caputo _publ_contact_author_email maria.cassani@unibo.it _publ_contact_author_name 'Maria-Cristina Cassani' data_p21n _database_code_depnum_ccdc_archive 'CCDC 837138' #TrackingRef '- P21n2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H30 Au2 N8 O8' _chemical_formula_weight 832.39 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' Au Au -2.0133 8.8022 '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)/n loop_ _symmetry_equiv_pos_as_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 7.501(3) _cell_length_b 10.545(5) _cell_length_c 14.899(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.806(6) _cell_angle_gamma 90.00 _cell_volume 1170.2(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4706 _cell_measurement_theta_min 2.372 _cell_measurement_theta_max 27.318 _exptl_crystal_description PRISMATIC _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 12.579 _exptl_absorpt_correction_type 'EMPIRICAL SADABS' _exptl_absorpt_correction_T_min 0.1876 _exptl_absorpt_correction_T_max 0.3660 _exptl_absorpt_process_details ? _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 'CCD AREA DETECTOR' _diffrn_measurement_method 'OMEGA SCANS' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10551 _diffrn_reflns_av_R_equivalents 0.1055 _diffrn_reflns_av_sigmaI/netI 0.0835 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2061 _reflns_number_gt 1507 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1437P)^2^+0.7969P] 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 2061 _refine_ls_number_parameters 147 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.2285 _refine_ls_wR_factor_gt 0.2091 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.062 _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 Au1 Au 0.16237(10) 0.04356(7) 0.07475(5) 0.0606(4) Uani 1 1 d . . . C1 C 0.300(2) 0.1270(19) -0.0167(11) 0.055(4) Uani 1 1 d . . . N2 N 0.384(2) 0.2364(16) -0.0077(11) 0.063(4) Uani 1 1 d . . . C3 C 0.470(3) 0.262(2) -0.0820(18) 0.084(6) Uani 1 1 d . . . H3 H 0.5356 0.3344 -0.0915 0.101 Uiso 1 1 calc R . . C4 C 0.444(3) 0.166(2) -0.1363(17) 0.079(6) Uani 1 1 d . . . H4 H 0.4886 0.1560 -0.1916 0.095 Uiso 1 1 calc R . . N5 N 0.335(2) 0.0781(19) -0.0951(12) 0.067(4) Uani 1 1 d . . . C6 C 0.385(3) 0.326(2) 0.0696(15) 0.077(6) Uani 1 1 d . . . H6A H 0.2930 0.3020 0.1062 0.116 Uiso 1 1 calc R . . H6B H 0.3618 0.4104 0.0471 0.116 Uiso 1 1 calc R . . H6C H 0.4997 0.3233 0.1055 0.116 Uiso 1 1 calc R . . N7 N 0.039(3) -0.0374(15) 0.1794(11) 0.064(4) Uani 1 1 d . . . H7A H 0.0379 -0.0615 0.1242 0.077 Uiso 1 1 calc R . . H7B H 0.1321 -0.0502 0.2176 0.077 Uiso 1 1 calc R . . C8 C -0.118(3) 0.025(2) 0.2080(15) 0.074(6) Uani 1 1 d . . . H8A H -0.0838 0.1084 0.2317 0.089 Uiso 1 1 calc R . . H8B H -0.1609 -0.0236 0.2563 0.089 Uiso 1 1 calc R . . C9 C -0.266(3) 0.0389(18) 0.1325(16) 0.071(5) Uani 1 1 d . . . H9A H -0.3638 0.0858 0.1544 0.085 Uiso 1 1 calc R . . H9B H -0.2231 0.0887 0.0848 0.085 Uiso 1 1 calc R . . N10 N 0.111(3) 0.636(2) 0.1959(12) 0.078(5) Uani 1 1 d . . . O11 O 0.238(2) 0.7000(18) 0.2234(13) 0.093(5) Uani 1 1 d . . . O12 O -0.038(2) 0.6727(15) 0.1757(13) 0.094(5) Uani 1 1 d . . . O13 O 0.136(3) 0.5160(19) 0.1947(17) 0.116(8) Uani 1 1 d . . . O20 O 0.781(4) 0.447(3) 0.083(3) 0.156(10) Uani 1 1 d U . . H20 H 0.8448 0.5069 0.1022 0.234 Uiso 1 1 calc R . . C21 C 0.886(5) 0.355(3) 0.052(3) 0.138(10) Uani 1 1 d U . . H21A H 0.9627 0.3909 0.0116 0.207 Uiso 1 1 calc R . . H21B H 0.8115 0.2909 0.0212 0.207 Uiso 1 1 calc R . . H21C H 0.9590 0.3170 0.1027 0.207 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 Au1 0.0623(6) 0.0578(6) 0.0623(6) 0.0037(3) 0.0094(4) -0.0033(3) C1 0.040(9) 0.076(12) 0.049(9) 0.012(9) 0.011(7) 0.000(8) N2 0.047(8) 0.074(11) 0.067(9) 0.018(8) 0.004(7) -0.008(7) C3 0.079(15) 0.070(15) 0.099(16) 0.019(13) -0.009(12) -0.004(11) C4 0.067(13) 0.080(15) 0.098(16) 0.008(13) 0.039(12) -0.009(10) N5 0.059(10) 0.075(11) 0.065(10) 0.013(8) -0.003(8) -0.001(7) C6 0.060(13) 0.088(16) 0.078(14) 0.004(11) -0.013(10) -0.014(10) N7 0.070(11) 0.076(12) 0.046(8) 0.005(7) 0.003(7) -0.006(8) C8 0.089(16) 0.074(15) 0.062(12) -0.004(10) 0.021(11) -0.010(11) C9 0.077(15) 0.064(14) 0.073(13) -0.003(10) 0.016(11) 0.006(10) N10 0.079(14) 0.084(14) 0.070(11) -0.008(10) -0.002(9) 0.002(11) O11 0.078(11) 0.105(13) 0.092(10) 0.016(10) -0.005(8) 0.002(10) O12 0.075(11) 0.068(10) 0.133(14) 0.017(9) -0.015(10) 0.007(8) O13 0.138(18) 0.062(11) 0.138(18) -0.019(11) -0.029(14) 0.020(11) O20 0.124(19) 0.14(2) 0.21(3) 0.005(16) 0.013(17) -0.019(13) C21 0.11(2) 0.10(2) 0.20(3) 0.006(18) 0.003(19) -0.014(14) _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 Au1 C1 2.006(16) . ? Au1 N7 2.089(17) . ? Au1 Au1 3.2332(17) 3 ? C1 N2 1.31(2) . ? C1 N5 1.33(3) . ? N2 C3 1.37(3) . ? N2 C6 1.49(3) . ? C3 C4 1.30(3) . ? C3 H3 0.9300 . ? C4 N5 1.42(3) . ? C4 H4 0.9300 . ? N5 C9 1.43(3) 3 ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? N7 C8 1.46(3) . ? N7 H7A 0.8600 . ? N7 H7B 0.8600 . ? C8 C9 1.49(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N5 1.43(3) 3 ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? N10 O12 1.19(2) . ? N10 O11 1.20(2) . ? N10 O13 1.28(3) . ? O20 C21 1.37(5) . ? O20 H20 0.8200 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 C1 Au1 N7 174.5(7) . . ? C1 Au1 Au1 93.6(5) . 3 ? N7 Au1 Au1 91.9(5) . 3 ? N2 C1 N5 106.5(15) . . ? N2 C1 Au1 126.5(14) . . ? N5 C1 Au1 126.8(15) . . ? C1 N2 C3 110.8(18) . . ? C1 N2 C6 126.4(16) . . ? C3 N2 C6 122.7(18) . . ? C4 C3 N2 107(2) . . ? C4 C3 H3 126.3 . . ? N2 C3 H3 126.3 . . ? C3 C4 N5 107(2) . . ? C3 C4 H4 126.6 . . ? N5 C4 H4 126.6 . . ? C1 N5 C4 108.3(19) . . ? C1 N5 C9 125.2(18) . 3 ? C4 N5 C9 126.5(19) . 3 ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 N7 Au1 118.7(13) . . ? C8 N7 H7A 120.0 . . ? Au1 N7 H7A 50.3 . . ? C8 N7 H7B 120.0 . . ? Au1 N7 H7B 99.2 . . ? H7A N7 H7B 120.0 . . ? N7 C8 C9 112.3(18) . . ? N7 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N7 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? N5 C9 C8 114.5(17) 3 . ? N5 C9 H9A 108.6 3 . ? C8 C9 H9A 108.6 . . ? N5 C9 H9B 108.6 3 . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? O12 N10 O11 126(2) . . ? O12 N10 O13 117(2) . . ? O11 N10 O13 117(2) . . ? C21 O20 H20 109.5 . . ? O20 C21 H21A 109.5 . . ? O20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 N7 Au1 C1 N2 -40(8) . . . . ? Au1 Au1 C1 N2 137.9(15) 3 . . . ? N7 Au1 C1 N5 135(7) . . . . ? Au1 Au1 C1 N5 -47.7(16) 3 . . . ? N5 C1 N2 C3 2(2) . . . . ? Au1 C1 N2 C3 177.3(14) . . . . ? N5 C1 N2 C6 -179.7(17) . . . . ? Au1 C1 N2 C6 -4(3) . . . . ? C1 N2 C3 C4 -2(3) . . . . ? C6 N2 C3 C4 179.8(18) . . . . ? N2 C3 C4 N5 1(3) . . . . ? N2 C1 N5 C4 -1(2) . . . . ? Au1 C1 N5 C4 -176.7(14) . . . . ? N2 C1 N5 C9 -178.2(18) . . . 3 ? Au1 C1 N5 C9 7(3) . . . 3 ? C3 C4 N5 C1 0(2) . . . . ? C3 C4 N5 C9 177(2) . . . 3 ? C1 Au1 N7 C8 104(7) . . . . ? Au1 Au1 N7 C8 -73.2(15) 3 . . . ? Au1 N7 C8 C9 58(2) . . . . ? N7 C8 C9 N5 62(2) . . . 3 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 4.122 _refine_diff_density_min -1.057 _refine_diff_density_rms 0.352