# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Dalton Trans. _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Kevin Flower' _publ_contact_author_email kevsnuts@hotmail.com _publ_section_title ; First structurally confirmed example of the formation of a gold(III) carbon bond via t ransmetallation with a boroxine. ; # Attachment '- Flower.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-07-28 at 13:29:02 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : new dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# #TrackingRef '- Flower.cif' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2011-07-28 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? _publ_requested_category FM loop_ _publ_author_name K.Flower A.Brisdon P.Quayle R.Pritchard G.Price #------------------ AUTHOR DETAILS -------------------------------------------# data_new _database_code_depnum_ccdc_archive 'CCDC 837221' #TrackingRef '- Flower.cif' _audit_creation_date 2011-07-28T13:29:02-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H14 Au1 Cl2 N1' _chemical_formula_sum 'C10 H14 Au Cl2 N' _chemical_formula_weight 416.09 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 8.7402(3) _cell_length_b 11.1657(5) _cell_length_c 16.9401(5) _cell_angle_alpha 90 _cell_angle_beta 135.074(2) _cell_angle_gamma 90 _cell_volume 1167.47(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2877 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 2.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 13.019 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2298 _exptl_absorpt_correction_T_max 0.5622 _exptl_absorpt_process_details ; Blessing, R. H. (1995) Acta Cryst., A51, 33-38. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.319875E-1 _diffrn_orient_matrix_ub_12 0.704295E-1 _diffrn_orient_matrix_ub_13 -0.507425E-1 _diffrn_orient_matrix_ub_21 0.271965E-1 _diffrn_orient_matrix_ub_22 -0.454971E-1 _diffrn_orient_matrix_ub_23 -0.61937E-1 _diffrn_orient_matrix_ub_31 -0.110888 _diffrn_orient_matrix_ub_32 -0.314752E-1 _diffrn_orient_matrix_ub_33 -0.240131E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_unetI/netI 0.0574 _diffrn_reflns_number 8932 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 2663 _reflns_number_gt 2372 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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. Electron density synthesis with coefficients Fo-Fc Highest peak 8.17 at 0.4383 0.6649 0.5416 [ 1.36 A from CL1 ] Deepest hole -2.27 at 0.3448 0.6173 0.5079 [ 0.84 A from AU1 ] The single high electron density peak is unsual and doesn't bear the hall marks of an absorption problem i.e. a cluster of peaks near the heavy atom. Twinning possibilites were explored thoroughly and did not produce a significant reduction in the peak height. It is therefore likely in the absence of any other sensible explanations that the surplus electron density is a symptom of stacking faults. ; _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^)+(0.0362P)^2^+26.3388P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0027(4) _refine_ls_number_reflns 2663 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 8.178 _refine_diff_density_min -2.275 _refine_diff_density_rms 0.296 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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' 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 C1 C 1.0976(15) 0.4131(7) 0.4404(8) 0.0159(17) Uani 1 1 d . . . C2 C 0.8720(15) 0.4153(8) 0.3555(8) 0.0198(18) Uani 1 1 d . . . C3 C 0.7606(17) 0.3089(9) 0.3258(9) 0.025(2) Uani 1 1 d . . . H3 H 0.6067 0.3094 0.2687 0.03 Uiso 1 1 calc R . . C4 C 0.8682(17) 0.2026(9) 0.3771(9) 0.025(2) Uani 1 1 d . . . H4 H 0.789 0.1306 0.3559 0.03 Uiso 1 1 calc R . . C5 C 1.0958(16) 0.2010(9) 0.4609(8) 0.0216(19) Uani 1 1 d . . . C6 C 1.2088(16) 0.3054(9) 0.4907(8) 0.0229(19) Uani 1 1 d . . . H6 H 1.3626 0.3043 0.5455 0.027 Uiso 1 1 calc R . . C7 C 0.7681(14) 0.5356(9) 0.3059(8) 0.0190(18) Uani 1 1 d . . . H7A H 0.6292 0.5264 0.2266 0.023 Uiso 1 1 calc R . . H7B H 0.7379 0.573 0.3467 0.023 Uiso 1 1 calc R . . C8 C 0.9135(18) 0.5814(10) 0.2273(9) 0.028(2) Uani 1 1 d . . . H8A H 1.0141 0.6335 0.2354 0.042 Uiso 1 1 calc R . . H8B H 0.7665 0.5927 0.153 0.042 Uiso 1 1 calc R . . H8C H 0.9569 0.4977 0.2363 0.042 Uiso 1 1 calc R . . C9 C 0.8503(18) 0.7395(10) 0.2989(9) 0.030(2) Uani 1 1 d . . . H9A H 0.9484 0.7911 0.3045 0.046 Uiso 1 1 calc R . . H9B H 0.8559 0.7619 0.3568 0.046 Uiso 1 1 calc R . . H9C H 0.702 0.7493 0.225 0.046 Uiso 1 1 calc R . . C10 C 1.217(2) 0.0821(9) 0.5185(10) 0.028(2) Uani 1 1 d . . . H10A H 1.3503 0.0816 0.5359 0.042 Uiso 1 1 calc R . . H10B H 1.1244 0.0151 0.4684 0.042 Uiso 1 1 calc R . . H10C H 1.253 0.0739 0.5877 0.042 Uiso 1 1 calc R . . N1 N 0.9178(13) 0.6125(8) 0.3144(7) 0.0205(16) Uani 1 1 d . . . Cl1 Cl 1.3620(4) 0.7730(2) 0.4900(2) 0.0264(5) Uani 1 1 d . . . Cl2 Cl 1.5589(4) 0.5177(2) 0.63873(19) 0.0224(5) Uani 1 1 d . . . Au1 Au 1.23081(5) 0.57647(3) 0.46959(3) 0.01796(17) Uani 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 C1 0.021(4) 0.009(4) 0.019(4) -0.003(3) 0.014(4) -0.003(3) C2 0.019(4) 0.023(5) 0.017(4) 0.002(4) 0.013(4) 0.003(4) C3 0.028(5) 0.021(5) 0.031(5) 0.000(4) 0.022(5) -0.003(4) C4 0.026(5) 0.018(5) 0.029(5) -0.005(4) 0.019(5) -0.008(4) C5 0.027(5) 0.018(5) 0.022(5) -0.001(4) 0.018(4) 0.001(4) C6 0.018(4) 0.028(5) 0.020(5) 0.009(4) 0.013(4) 0.001(4) C7 0.014(4) 0.024(5) 0.017(4) 0.001(4) 0.011(4) -0.002(4) C8 0.026(5) 0.041(6) 0.018(5) 0.004(4) 0.016(4) 0.007(4) C9 0.027(5) 0.023(5) 0.029(5) 0.004(4) 0.016(5) 0.006(4) C10 0.041(6) 0.022(5) 0.030(6) 0.002(4) 0.028(5) 0.003(4) N1 0.019(4) 0.020(4) 0.014(4) 0.006(3) 0.009(3) 0.004(3) Cl1 0.0252(11) 0.0201(11) 0.0298(12) 0.0020(9) 0.0180(10) -0.0013(9) Cl2 0.0159(10) 0.0225(11) 0.0199(11) 0.0000(9) 0.0095(9) 0.0007(8) Au1 0.0176(2) 0.0169(2) 0.0174(2) 0.00081(12) 0.01172(19) 0.00053(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C2 1.393(13) . ? C1 C6 1.394(13) . ? C1 Au1 2.028(8) . ? C2 C3 1.385(14) . ? C2 C7 1.502(13) . ? C3 C4 1.375(14) . ? C3 H3 0.95 . ? C4 C5 1.405(14) . ? C4 H4 0.95 . ? C5 C6 1.373(14) . ? C5 C10 1.540(14) . ? C6 H6 0.95 . ? C7 N1 1.484(12) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 N1 1.490(12) . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 N1 1.486(13) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? N1 Au1 2.091(8) . ? Cl1 Au1 2.385(2) . ? Cl2 Au1 2.287(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 C2 C1 C6 120.7(8) . . ? C2 C1 Au1 112.6(6) . . ? C6 C1 Au1 126.5(7) . . ? C3 C2 C1 118.5(9) . . ? C3 C2 C7 124.9(9) . . ? C1 C2 C7 116.5(8) . . ? C4 C3 C2 121.4(9) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 119.7(9) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 119.7(9) . . ? C6 C5 C10 120.4(9) . . ? C4 C5 C10 119.8(9) . . ? C5 C6 C1 119.9(9) . . ? C5 C6 H6 120 . . ? C1 C6 H6 120 . . ? N1 C7 C2 108.7(7) . . ? N1 C7 H7A 109.9 . . ? C2 C7 H7A 109.9 . . ? N1 C7 H7B 109.9 . . ? C2 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 N1 C9 108.8(8) . . ? C7 N1 C8 111.5(8) . . ? C9 N1 C8 108.5(8) . . ? C7 N1 Au1 106.8(6) . . ? C9 N1 Au1 114.1(6) . . ? C8 N1 Au1 107.0(6) . . ? C1 Au1 N1 81.5(4) . . ? C1 Au1 Cl2 92.4(3) . . ? N1 Au1 Cl2 173.8(2) . . ? C1 Au1 Cl1 175.6(3) . . ? N1 Au1 Cl1 94.1(2) . . ? Cl2 Au1 Cl1 92.00(9) . . ? # END of CIF