# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1526 data_quarto _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 Au2 Br2 Cl2 N2' _chemical_formula_weight 780.84 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' 'Cl' 'Cl' 0.1484 0.1585 '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' 'Br' 'Br' -0.2901 2.4595 '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' _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 7.5360(8) _cell_length_b 14.4660(14) _cell_length_c 14.0832(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.951(8) _cell_angle_gamma 90.00 _cell_volume 1502.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 64 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 12.4 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 25.170 _exptl_absorpt_correction_type 'psi scans' _exptl_absorpt_correction_T_min 0.409 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens P4' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 247 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3122 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 2 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2636 _reflns_number_gt 1959 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens XP5' _computing_publication_material 'Siemens XP5' _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^)+(0.0517P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2636 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _refine_ls_shift/su_max 0.005 _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 0.31515(7) 0.49095(3) 0.54562(3) 0.01718(15) Uani 1 1 d . . . Au2 Au 0.44777(7) 0.27545(3) 0.56603(3) 0.01870(15) Uani 1 1 d . . . Cl1 Cl 0.1938(5) 0.2715(2) 0.6286(2) 0.0253(7) Uani 1 1 d . . . Cl2 Cl 0.7025(4) 0.2731(2) 0.5051(2) 0.0230(7) Uani 1 1 d . . . Br1 Br -0.0450(2) 0.60950(9) 0.16299(9) 0.0271(3) Uani 1 1 d . . . N1 N 0.1456(14) 0.4664(7) 0.4181(7) 0.018(2) Uani 1 1 d . . . C2 C 0.1113(18) 0.5324(8) 0.3457(9) 0.020(3) Uani 1 1 d . . . H2 H 0.1682 0.5912 0.3567 0.024 Uiso 1 1 calc R . . C3 C -0.0012(17) 0.5154(9) 0.2599(9) 0.021(3) Uani 1 1 d . . . C4 C -0.0893(18) 0.4302(9) 0.2388(9) 0.021(3) Uani 1 1 d . . . H4 H -0.1666 0.4183 0.1777 0.025 Uiso 1 1 calc R . . C5 C -0.0581(19) 0.3649(9) 0.3110(9) 0.024(3) Uani 1 1 d . . . H5 H -0.1169 0.3065 0.3009 0.029 Uiso 1 1 calc R . . C6 C 0.0611(17) 0.3839(9) 0.4004(9) 0.021(3) Uani 1 1 d . . . H6 H 0.0822 0.3376 0.4493 0.026 Uiso 1 1 calc R . . Br1' Br 0.5997(2) 0.38644(9) 0.94214(9) 0.0278(3) Uani 1 1 d . . . N1' N 0.4636(17) 0.5218(7) 0.6797(7) 0.023(3) Uani 1 1 d . . . C2' C 0.4864(18) 0.4566(9) 0.7519(9) 0.021(3) Uani 1 1 d . . . H2' H 0.4375 0.3964 0.7383 0.025 Uiso 1 1 calc R . . C3' C 0.5779(19) 0.4774(8) 0.8425(8) 0.018(3) Uani 1 1 d . . . C4' C 0.6553(16) 0.5636(9) 0.8663(9) 0.020(3) Uani 1 1 d . . . H4' H 0.7192 0.5780 0.9301 0.024 Uiso 1 1 calc R . . C5' C 0.6335(18) 0.6276(9) 0.7911(10) 0.024(3) Uani 1 1 d . . . H5' H 0.6843 0.6877 0.8026 0.029 Uiso 1 1 calc R . . C6' C 0.5387(19) 0.6041(8) 0.7001(9) 0.022(3) Uani 1 1 d . . . H6' H 0.5266 0.6488 0.6497 0.027 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 0.0194(3) 0.0178(3) 0.0116(2) -0.0008(2) -0.00310(18) -0.0003(2) Au2 0.0231(3) 0.0141(3) 0.0156(2) 0.0003(2) -0.00349(19) 0.0008(2) Cl1 0.0253(18) 0.0252(17) 0.0241(16) 0.0030(14) 0.0020(14) 0.0013(15) Cl2 0.0267(18) 0.0175(15) 0.0219(16) 0.0025(13) -0.0018(13) 0.0014(15) Br1 0.0357(8) 0.0243(7) 0.0184(7) 0.0065(5) -0.0006(6) 0.0039(6) N1 0.013(6) 0.018(6) 0.020(6) -0.007(4) -0.002(4) -0.002(5) C2 0.028(8) 0.006(6) 0.021(7) 0.003(5) -0.004(6) -0.003(5) C3 0.017(7) 0.035(8) 0.012(6) -0.002(6) 0.004(5) 0.004(6) C4 0.024(7) 0.023(7) 0.012(6) -0.005(5) -0.002(5) 0.009(6) C5 0.036(8) 0.015(7) 0.021(7) -0.008(5) 0.006(6) -0.002(6) C6 0.022(7) 0.021(7) 0.018(7) 0.005(5) 0.000(6) 0.000(6) Br1' 0.0382(8) 0.0237(7) 0.0192(7) 0.0063(5) 0.0002(6) -0.0001(6) N1' 0.043(7) 0.016(6) 0.008(5) -0.003(4) 0.000(5) 0.001(5) C2' 0.026(8) 0.011(6) 0.028(7) 0.000(5) 0.012(6) 0.009(6) C3' 0.033(8) 0.012(6) 0.007(6) 0.003(5) 0.000(5) 0.008(6) C4' 0.012(7) 0.022(7) 0.021(7) 0.000(6) -0.008(5) -0.006(6) C5' 0.026(8) 0.012(7) 0.034(8) 0.002(6) 0.005(6) -0.003(6) C6' 0.039(9) 0.012(6) 0.017(7) 0.001(5) 0.009(6) 0.000(6) _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. Operators $1 -x+1, -y+1, -z+1 $2 0.5-x, 0.5+y, 0.5-z $3 1.5-x, 0.5+y, 1.5-z $4 0.5+x, 0.5-y, 0.5+z $5 -0.5+x, 0.5-y, -0.5+z Distance MORE 3.4849 (0.0031) Cl2 - Au1_$1 3.4413 (0.0035) Br1' - Cl1_$4 3.3836 (0.0033) Br1 - Cl2_$2 Angle MORE 173.09 ( 0.44) C3' - Br1' - Cl1_$4 169.56 ( 0.39) C3 - Br1 - Cl2_$2 ; 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 N1 2.009(10) . y Au1 N1' 2.035(10) . y Au1 Au2 3.2681(7) . y Au1 Au1 3.3113(10) 3_666 y Au2 Cl2 2.259(3) . y Au2 Cl1 2.267(3) . y Br1 C3 1.908(13) . y N1 C6 1.350(16) . y N1 C2 1.381(15) . y C2 C3 1.348(18) . y C3 C4 1.402(18) . y C4 C5 1.373(18) . y C5 C6 1.414(18) . y Br1' C3' 1.906(11) . y N1' C6' 1.325(16) . y N1' C2' 1.371(16) . y C2' C3' 1.352(18) . y C3' C4' 1.387(17) . y C4' C5' 1.391(18) . y C5' C6' 1.374(19) . y 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 Au1 N1' 173.8(4) . . y N1 Au1 Au2 92.1(3) . . y N1' Au1 Au2 91.6(3) . . y N1 Au1 Au1 95.6(3) . 3_666 y N1' Au1 Au1 89.9(3) . 3_666 y Au2 Au1 Au1 80.97(2) . 3_666 y Cl2 Au2 Cl1 177.61(12) . . y Cl2 Au2 Au1 104.46(8) . . y Cl1 Au2 Au1 77.93(8) . . y C6 N1 C2 117.8(11) . . y C6 N1 Au1 120.6(8) . . y C2 N1 Au1 121.6(8) . . y C3 C2 N1 121.4(12) . . y C2 C3 C4 122.3(12) . . y C2 C3 Br1 119.6(10) . . y C4 C3 Br1 118.1(9) . . y C5 C4 C3 116.5(12) . . y C4 C5 C6 120.3(12) . . y N1 C6 C5 121.6(12) . . y C6' N1' C2' 118.4(11) . . y C6' N1' Au1 121.7(9) . . y C2' N1' Au1 119.9(9) . . y C3' C2' N1' 120.5(12) . . y C2' C3' C4' 122.3(11) . . y C2' C3' Br1' 119.3(10) . . y C4' C3' Br1' 118.3(9) . . y C3' C4' C5' 115.8(11) . . y C6' C5' C4' 120.2(12) . . y N1' C6' C5' 122.7(12) . . y 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 N1 Au1 Au2 Cl2 94.9(3) . . . . y N1' Au1 Au2 Cl2 -90.1(3) . . . . y Au1 Au1 Au2 Cl2 -0.48(8) 3_666 . . . y N1 Au1 Au2 Cl1 -85.2(3) . . . . y N1' Au1 Au2 Cl1 89.8(3) . . . . y Au1 Au1 Au2 Cl1 179.45(9) 3_666 . . . y N1' Au1 N1 C6 -93(4) . . . . y Au2 Au1 N1 C6 33.1(9) . . . . y Au1 Au1 N1 C6 114.2(9) 3_666 . . . y N1' Au1 N1 C2 87(4) . . . . y Au2 Au1 N1 C2 -146.9(9) . . . . y Au1 Au1 N1 C2 -65.8(9) 3_666 . . . y C6 N1 C2 C3 -0.6(18) . . . . y Au1 N1 C2 C3 179.3(10) . . . . y N1 C2 C3 C4 0(2) . . . . y N1 C2 C3 Br1 179.5(9) . . . . y C2 C3 C4 C5 1.2(19) . . . . y Br1 C3 C4 C5 -178.5(9) . . . . y C3 C4 C5 C6 -1.5(18) . . . . y C2 N1 C6 C5 0.3(18) . . . . y Au1 N1 C6 C5 -179.7(10) . . . . y C4 C5 C6 N1 1(2) . . . . y N1 Au1 N1' C6' -86(4) . . . . y Au2 Au1 N1' C6' 147.2(10) . . . . y Au1 Au1 N1' C6' 66.3(10) 3_666 . . . y N1 Au1 N1' C2' 93(4) . . . . y Au2 Au1 N1' C2' -33.3(9) . . . . y Au1 Au1 N1' C2' -114.3(9) 3_666 . . . y C6' N1' C2' C3' 2.4(18) . . . . y Au1 N1' C2' C3' -177.1(10) . . . . y N1' C2' C3' C4' -1(2) . . . . y N1' C2' C3' Br1' 177.8(9) . . . . y C2' C3' C4' C5' -0.2(19) . . . . y Br1' C3' C4' C5' -179.3(9) . . . . y C3' C4' C5' C6' 0.6(19) . . . . y C2' N1' C6' C5' -2(2) . . . . y Au1 N1' C6' C5' 177.4(10) . . . . y C4' C5' C6' N1' 1(2) . . . . y 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 C2' H2' Cl1 0.95 2.80 3.670(14) 152.3 . C2 H2 Cl2 0.95 2.79 3.616(13) 145.4 3_666 C4' H4' Cl2 0.95 2.99 3.578(13) 121.7 2_656 C4 H4 Cl1 0.95 2.97 3.542(13) 120.0 4_565 C5' H5' Cl2 0.95 2.94 3.567(14) 124.9 2_656 C5 H5 Cl1 0.95 2.79 3.464(13) 129.0 4_565 C6' H6' Cl2 0.95 2.73 3.555(14) 145.6 3_666 C6 H6 Cl1 0.95 2.67 3.555(13) 155.7 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.829 _refine_diff_density_min -1.834 _refine_diff_density_rms 0.364