# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Yukihiro Yoshida' _publ_contact_author_address ; Division of Chemistry, Graduate School of Science Kyoto University Sakyo-ku Kyoto 606-8502 JAPAN ; _publ_contact_author_email YOSHIDAY@KUCHEM.KYOTO-U.AC.JP _publ_section_title ; Dicyanoaurate(I) salts with 1-alkyl-3-methylimidazolium: room-temperature liquid forming and luminescent properties ; loop_ _publ_author_name 'Yukihiro Yoshida' 'Junichi Fujii' 'Takaaki Hiramatsu' 'Gunzi Saito' 'Naoki Sato' # Attachment 'HMI-Au(CN)2.cif' data_HMI-Au(CN)2 _database_code_depnum_ccdc_archive 'CCDC 280734' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common HMI-Au(CN)2 _chemical_formula_moiety ? _chemical_formula_sum 'C6 H7 Au1 N4' _chemical_formula_weight 332.12 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9146(14) _cell_length_b 7.0143(19) _cell_length_c 10.590(2) _cell_angle_alpha 100.178(19) _cell_angle_beta 97.310(17) _cell_angle_gamma 117.655(16) _cell_volume 434.71(17) _cell_formula_units_Z 2 _cell_measurement_temperature 'room temperature' _cell_measurement_reflns_used 22 _cell_measurement_theta_min 13.79 _cell_measurement_theta_max 16.81 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.538 _exptl_crystal_F_000 150 _exptl_absorpt_coefficient_mu 168.62 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 'room temperature' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K-alpha' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Mac Science MXC18' _diffrn_measurement_method theta/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2219 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.39 _reflns_number_total 1355 _reflns_threshold_expression >4sigma(I) _computing_data_collection 'MXC(MAC Science)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_reduction Crystan _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III' _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 w=1/[\s^2^(Fo^2^)+(0.0964P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1199 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.0559 _refine_ls_wR_factor_all 0.1952 _refine_ls_goodness_of_fit_all 1.450 _refine_ls_restrained_S_all 1.450 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.040(3) 0.308(3) 0.146(2) 0.068(5) Uani 1 d . . . H2 H -0.0688 0.3216 0.1954 0.081 Uiso 1 calc R . . C4 C 0.335(3) 0.306(3) 0.0975(17) 0.061(4) Uani 1 d . . . H4 H 0.4861 0.3169 0.1076 0.073 Uiso 1 calc R . . C5 C 0.198(3) 0.268(3) -0.016(2) 0.067(4) Uani 1 d . . . H5 H 0.2239 0.2448 -0.1063 0.081 Uiso 1 calc R . . C6 C 0.336(3) 0.385(4) 0.344(2) 0.090(6) Uani 1 d . . . H6A H 0.4849 0.5251 0.3687 0.108 Uiso 1 calc R . . H6B H 0.3565 0.2598 0.3630 0.108 Uiso 1 calc R . . H6C H 0.2343 0.4070 0.3971 0.108 Uiso 1 calc R . . C11 C -0.030(3) 0.260(3) 0.601(2) 0.063(4) Uani 1 d . . . C12 C -0.480(3) -0.064(3) 0.261(2) 0.069(5) Uani 1 d . . . N1 N 0.012(2) 0.269(2) 0.0180(17) 0.068(4) Uani 1 d . . . H1 H -0.1230 0.2430 -0.0457 0.082 Uiso 1 calc R . . N3 N 0.231(2) 0.328(2) 0.1986(13) 0.057(3) Uani 1 d . . . N11 N 0.111(3) 0.363(3) 0.6943(19) 0.086(5) Uani 1 d . . . N12 N -0.604(3) -0.151(3) 0.1570(17) 0.077(4) Uani 1 d . . . Au1 Au -0.26055(10) 0.09119(11) 0.43186(7) 0.0607(3) Uani 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 C2 0.057(8) 0.064(10) 0.078(15) 0.013(9) 0.011(8) 0.030(7) C4 0.062(8) 0.079(10) 0.045(10) 0.022(8) 0.015(7) 0.036(8) C5 0.072(10) 0.057(9) 0.064(12) 0.013(8) 0.020(8) 0.025(7) C6 0.075(12) 0.127(18) 0.065(14) 0.029(13) 0.018(10) 0.047(12) C11 0.064(9) 0.078(10) 0.062(12) 0.024(10) 0.023(8) 0.044(8) C12 0.059(8) 0.069(10) 0.086(15) 0.024(10) 0.014(9) 0.036(8) N1 0.067(8) 0.050(7) 0.078(12) 0.015(7) -0.003(7) 0.026(6) N3 0.058(7) 0.057(7) 0.046(8) 0.019(6) 0.002(5) 0.023(5) N11 0.063(9) 0.116(13) 0.064(12) 0.008(10) 0.010(7) 0.039(9) N12 0.070(9) 0.086(10) 0.062(11) 0.016(8) 0.000(7) 0.033(8) Au1 0.0549(3) 0.0710(4) 0.0580(5) 0.0175(3) 0.0118(2) 0.0329(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 C2 N1 1.30(2) . ? C2 N3 1.31(2) . ? C4 C5 1.33(2) . ? C4 N3 1.39(2) . ? C5 N1 1.38(2) . ? C6 N3 1.51(2) . ? C11 N11 1.14(2) . ? C11 Au1 1.979(19) . ? C12 N12 1.17(3) . ? C12 Au1 1.96(2) . ? 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 N1 C2 N3 109.5(16) . . ? C5 C4 N3 107.6(15) . . ? C4 C5 N1 106.0(17) . . ? N11 C11 Au1 176.2(17) . . ? N12 C12 Au1 177.3(17) . . ? C2 N1 C5 109.3(15) . . ? C2 N3 C4 107.6(15) . . ? C2 N3 C6 127.2(16) . . ? C4 N3 C6 125.0(14) . . ? C12 Au1 C11 177.2(7) . . ? _diffrn_measured_fraction_theta_max 0.686 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.686 _refine_diff_density_max 2.196 _refine_diff_density_min -1.950 _refine_diff_density_rms 0.287 # Attachment 'EMI-Au(CN)2.cif' data_EMI-Au(CN)2 _database_code_depnum_ccdc_archive 'CCDC 280735' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common EMI-Au(CN)2 _chemical_formula_moiety ? _chemical_formula_sum 'C8 H11 Au1 N4' _chemical_formula_weight 360.16 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' 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 '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 8.3701(17) _cell_length_b 19.900(4) _cell_length_c 6.6722(18) _cell_angle_alpha 90.00 _cell_angle_beta 107.837(19) _cell_angle_gamma 90.00 _cell_volume 1057.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 'room temperature' _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.262 _exptl_crystal_F_000 166 _exptl_absorpt_coefficient_mu 138.68 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 'room temperature' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K-alpha' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Mac Science MXC18' _diffrn_measurement_method theta/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2426 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2170 _reflns_threshold_expression >4sigma(I) _computing_data_collection 'MXC(MAC Science)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_reduction Crystan _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III' _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 w=1/[\s^2^(Fo^2^)+(0.0774P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1387 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.0430 _refine_ls_wR_factor_all 0.1312 _refine_ls_goodness_of_fit_all 1.207 _refine_ls_restrained_S_all 1.207 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.2351(13) 0.4253(5) 0.7053(17) 0.055(3) Uani 1 d . . . H2 H 0.3218 0.3960 0.6744 0.066 Uiso 1 calc R . . C4 C 0.1054(13) 0.5122(5) 0.7713(15) 0.048(2) Uani 1 d . . . H4 H 0.0786 0.5596 0.7990 0.058 Uiso 1 calc R . . C5 C 0.0083(13) 0.4588(5) 0.7649(15) 0.050(2) Uani 1 d . . . H5 H -0.1049 0.4589 0.7863 0.060 Uiso 1 calc R . . C6 C 0.3882(15) 0.5308(6) 0.7173(18) 0.070(3) Uani 1 d . . . H6A H 0.4905 0.5019 0.7477 0.084 Uiso 1 calc R . . H6B H 0.4092 0.5685 0.8214 0.084 Uiso 1 calc R . . H6C H 0.3618 0.5496 0.5718 0.084 Uiso 1 calc R . . C7 C 0.0396(16) 0.3329(6) 0.718(2) 0.078(4) Uani 1 d . . . H7A H -0.0209 0.3253 0.8242 0.094 Uiso 1 calc R . . H7B H 0.1422 0.3039 0.7573 0.094 Uiso 1 calc R . . C8 C -0.071(2) 0.3130(6) 0.507(2) 0.095(5) Uani 1 d . . . H8A H -0.1654 0.3458 0.4583 0.114 Uiso 1 calc R . . H8B H -0.1169 0.2671 0.5141 0.114 Uiso 1 calc R . . H8C H -0.0045 0.3128 0.4048 0.114 Uiso 1 calc R . . C11 C 0.6021(14) 0.3274(6) 0.8384(18) 0.060(3) Uani 1 d . . . C12 C 0.3226(17) 0.1606(6) 0.7572(19) 0.065(3) Uani 1 d . . . N1 N 0.0901(10) 0.4040(4) 0.7242(12) 0.0484(19) Uani 1 d . . . N3 N 0.2472(10) 0.4908(4) 0.7333(12) 0.0498(19) Uani 1 d . . . N11 N 0.6725(14) 0.3762(5) 0.8530(18) 0.077(3) Uani 1 d . . . N12 N 0.2459(15) 0.1135(6) 0.7361(18) 0.082(3) Uani 1 d . . . Au1 Au 0.46397(5) 0.243347(19) 0.79537(7) 0.05181(17) Uani 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 C2 0.050(6) 0.055(6) 0.062(6) -0.004(5) 0.020(5) 0.012(4) C4 0.054(6) 0.046(5) 0.049(5) -0.012(4) 0.020(5) 0.001(4) C5 0.048(6) 0.056(6) 0.049(6) -0.004(4) 0.020(4) 0.004(4) C6 0.053(7) 0.082(8) 0.078(8) -0.008(6) 0.024(6) -0.016(6) C7 0.070(8) 0.045(6) 0.123(12) 0.007(7) 0.034(8) 0.000(5) C8 0.107(11) 0.056(8) 0.118(12) -0.030(7) 0.031(9) -0.027(7) C11 0.043(6) 0.079(8) 0.062(7) -0.005(6) 0.022(5) 0.010(5) C12 0.073(8) 0.069(7) 0.055(7) 0.007(5) 0.020(6) 0.004(6) N1 0.042(4) 0.050(5) 0.052(5) -0.003(4) 0.012(4) 0.001(3) N3 0.047(5) 0.061(5) 0.045(5) -0.002(4) 0.019(4) -0.003(4) N11 0.069(7) 0.071(7) 0.101(9) -0.020(6) 0.040(6) -0.017(5) N12 0.092(9) 0.073(7) 0.090(8) -0.007(6) 0.040(7) -0.023(6) Au1 0.0445(2) 0.0540(3) 0.0571(3) -0.00033(19) 0.01581(17) 0.00475(17) _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 C2 N3 1.317(13) . ? C2 N1 1.327(13) . ? C4 C5 1.332(15) . ? C4 N3 1.356(12) . ? C5 N1 1.358(13) . ? C6 N3 1.455(12) . ? C7 N1 1.473(13) . ? C7 C8 1.484(18) . ? C11 N11 1.124(14) . ? C11 Au1 2.004(13) . ? C12 N12 1.121(15) . ? C12 Au1 1.997(13) . ? Au1 Au1 3.3466(9) 4_565 ? Au1 Au1 3.3466(9) 4_566 ? 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 N3 C2 N1 109.6(9) . . ? C5 C4 N3 107.7(9) . . ? C4 C5 N1 107.9(9) . . ? N1 C7 C8 111.8(11) . . ? N11 C11 Au1 175.9(12) . . ? N12 C12 Au1 178.7(13) . . ? C2 N1 C5 107.1(9) . . ? C2 N1 C7 124.5(9) . . ? C5 N1 C7 128.2(10) . . ? C2 N3 C4 107.7(8) . . ? C2 N3 C6 124.1(9) . . ? C4 N3 C6 128.2(9) . . ? C12 Au1 C11 178.4(4) . . ? C12 Au1 Au1 96.8(3) . 4_565 ? C11 Au1 Au1 84.3(3) . 4_565 ? C12 Au1 Au1 90.7(3) . 4_566 ? C11 Au1 Au1 88.1(3) . 4_566 ? Au1 Au1 Au1 170.92(3) 4_565 4_566 ? _diffrn_measured_fraction_theta_max 0.675 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.675 _refine_diff_density_max 1.129 _refine_diff_density_min -2.930 _refine_diff_density_rms 0.335