data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Thieuleux, Chloe' _publ_contact_author_email thieuleux@cpe.fr _publ_section_title ; Highly Efficient Gold(I) N-heterocyclic Carbenes Complexes for Alcohols Addition to Internal Alkynes ; loop_ _publ_author_name M.Bouhrara E.Jeanneau L.Veyre C.Coperet C.Thieuleux data_1 _database_code_depnum_ccdc_archive 'CCDC 763439' _audit_creation_date 10-01-26 _audit_creation_method CRYSTALS_ver_14.03 _oxford_structure_analysis_title 'import in P 2/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.4696(2) _cell_length_b 11.5952(2) _cell_length_c 9.5469(2) _cell_angle_alpha 90 _cell_angle_beta 119.3890(10) _cell_angle_gamma 90 _cell_volume 913.36(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 c 1 ' _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z x,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Au -2.0133 8.8022 16.8819 0.4611 18.5913 8.6216 25.5582 1.4826 5.8600 36.3956 12.0658 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C18 H42 Au1 Cl1 N4 # Dc = 1.99 Fooo = 488.00 Mu = 82.09 M = 546.98 # Found Formula = C19 H20 Au1 Cl1 N2 # Dc = 1.85 FOOO = 488.00 Mu = 82.00 M = 508.80 _chemical_formula_sum 'C19 H20 Au1 Cl1 N2' _chemical_formula_moiety 'C19 H20 Au1 Cl1 N2' _chemical_compound_source ? _chemical_formula_weight 508.80 _cell_measurement_reflns_used 2284 _cell_measurement_theta_min 0.679 _cell_measurement_theta_max 27.878 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.243 _exptl_crystal_size_mid 0.354 _exptl_crystal_size_max 0.425 _exptl_crystal_density_diffrn 1.850 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 8.200 # Sheldrick geometric approximatio 0.05 0.14 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor,1997)' _exptl_absorpt_correction_T_min 0.05 _exptl_absorpt_correction_T_max 0.14 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 3881 _reflns_number_total 3881 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections without Friedels Law is 3881 # Number of reflections with Friedels Law is 2182 # Theoretical number of reflections is about 2178 _diffrn_reflns_theta_min 1.756 _diffrn_reflns_theta_max 27.870 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.312 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min -12 _reflns_limit_l_max 12 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.78 _refine_diff_density_max 0.89 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 3873 _refine_ls_number_restraints 2 _refine_ls_number_parameters 210 _oxford_refine_ls_R_factor_ref 0.0225 _refine_ls_wR_factor_ref 0.0571 _refine_ls_goodness_of_fit_ref 1.2724 _refine_ls_shift/su_max 0.0010150 # The values computed from all data _oxford_reflns_number_all 3873 _refine_ls_R_factor_all 0.0225 _refine_ls_wR_factor_all 0.0571 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3785 _refine_ls_R_factor_gt 0.0220 _refine_ls_wR_factor_gt 0.0567 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.02P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Grazia, A., Moliterni, G., Polidori, G. & Spagna, R. (1999). J. App. Cryst. 32, 115-119. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Au1 Au 0.01437(12) 0.314787(11) 0.72775(13) 0.0216 1.0000 Uani . . . . . . . Cl2 Cl -0.1654(2) 0.33752(17) 0.8197(2) 0.0314 1.0000 Uani . . . . . . . C3 C 0.1712(8) 0.2932(6) 0.6531(8) 0.0247 1.0000 Uani . . . . . . . N4 N 0.3269(5) 0.3349(4) 0.7243(5) 0.0260 1.0000 Uani . . . . . . . C5 C 0.3997(7) 0.4141(5) 0.8609(6) 0.0359 1.0000 Uani . . . . . . . C6 C 0.4186(6) 0.5342(5) 0.8103(6) 0.0276 1.0000 Uani . . . . . . . C7 C 0.2867(6) 0.5914(5) 0.6910(6) 0.0311 1.0000 Uani . . . . . . . C8 C 0.3015(8) 0.7042(5) 0.6487(7) 0.0334 1.0000 Uani . . . . . . . C9 C 0.4515(7) 0.7590(5) 0.7272(7) 0.0337 1.0000 Uani . . . . . . . C10 C 0.5825(7) 0.7010(5) 0.8462(8) 0.0338 1.0000 Uani . . . . . . . C11 C 0.5683(6) 0.5903(5) 0.8878(6) 0.0301 1.0000 Uani . . . . . . . C12 C 0.4058(7) 0.2997(5) 0.6415(8) 0.0341 1.0000 Uani . . . . . . . C13 C 0.3006(6) 0.2335(5) 0.5204(7) 0.0303 1.0000 Uani . . . . . . . N14 N 0.1599(5) 0.2311(4) 0.5301(5) 0.0247 1.0000 Uani . . . . . . . C15 C 0.0155(7) 0.1715(4) 0.4144(7) 0.0244 1.0000 Uani . . . . . . . C16 C -0.0093(8) 0.0562(5) 0.4419(9) 0.0383 1.0000 Uani . . . . . . . C17 C -0.1440(12) -0.0008(8) 0.3210(13) 0.0544 1.0000 Uani . . . . . . . C18 C -0.2463(8) 0.0516(6) 0.1804(10) 0.0503 1.0000 Uani . . . . . . . C19 C -0.2206(8) 0.1658(6) 0.1559(8) 0.0404 1.0000 Uani . . . . . . . C20 C -0.0904(6) 0.2297(5) 0.2737(7) 0.0275 1.0000 Uani . . . . . . . C21 C -0.0694(7) 0.3544(6) 0.2485(7) 0.0368 1.0000 Uani . . . . . . . C22 C -0.3860(11) -0.0150(9) 0.0471(12) 0.0843 1.0000 Uani . . . . . . . C23 C 0.1076(12) -0.0007(7) 0.5973(13) 0.0586 1.0000 Uani . . . . . . . H51 H 0.3307 0.4169 0.9107 0.0440 1.0000 Uiso R . . . . . . H52 H 0.5057 0.3841 0.9391 0.0443 1.0000 Uiso R . . . . . . H71 H 0.1869 0.5518 0.6370 0.0400 1.0000 Uiso R . . . . . . H81 H 0.2104 0.7435 0.5670 0.0405 1.0000 Uiso R . . . . . . H91 H 0.4621 0.8314 0.7010 0.0438 1.0000 Uiso R . . . . . . H101 H 0.6826 0.7362 0.8988 0.0429 1.0000 Uiso R . . . . . . H111 H 0.6589 0.5506 0.9687 0.0372 1.0000 Uiso R . . . . . . H121 H 0.5103 0.3184 0.6645 0.0413 1.0000 Uiso R . . . . . . H131 H 0.3184 0.1957 0.4446 0.0377 1.0000 Uiso R . . . . . . H171 H -0.1628 -0.0764 0.3382 0.0715 1.0000 Uiso R . . . . . . H191 H -0.2911 0.2007 0.0573 0.0511 1.0000 Uiso R . . . . . . H211 H -0.1304 0.3704 0.1368 0.0591 1.0000 Uiso R . . . . . . H212 H -0.1044 0.4047 0.3060 0.0595 1.0000 Uiso R . . . . . . H213 H 0.0406 0.3691 0.2822 0.0588 1.0000 Uiso R . . . . . . H221 H -0.4720 0.0368 -0.0200 0.1260 1.0000 Uiso R . . . . . . H222 H -0.4247 -0.0724 0.0924 0.1260 1.0000 Uiso R . . . . . . H223 H -0.3465 -0.0518 -0.0168 0.1260 1.0000 Uiso R . . . . . . H231 H 0.0631 -0.0717 0.6083 0.1010 1.0000 Uiso R . . . . . . H232 H 0.1287 0.0496 0.6851 0.1010 1.0000 Uiso R . . . . . . H233 H 0.2053 -0.0153 0.5947 0.1008 1.0000 Uiso 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 0.01731(8) 0.02608(9) 0.02145(8) -0.00039(11) 0.00960(6) -0.00116(10) Cl2 0.0206(7) 0.0458(8) 0.0312(7) -0.0009(8) 0.0153(6) 0.0019(7) C3 0.016(3) 0.029(3) 0.026(3) -0.002(3) 0.008(2) -0.010(2) N4 0.014(2) 0.040(2) 0.020(2) 0.0034(18) 0.0058(17) -0.0040(17) C5 0.026(3) 0.048(3) 0.027(2) -0.002(2) 0.008(2) -0.015(2) C6 0.023(2) 0.038(3) 0.022(2) -0.003(2) 0.012(2) -0.006(2) C7 0.021(2) 0.047(3) 0.022(2) -0.008(2) 0.008(2) -0.003(2) C8 0.033(3) 0.038(3) 0.025(3) -0.008(2) 0.011(2) 0.008(2) C9 0.044(3) 0.029(3) 0.029(2) -0.004(2) 0.018(2) 0.000(2) C10 0.025(3) 0.041(3) 0.039(3) -0.006(2) 0.018(2) -0.007(2) C11 0.018(2) 0.040(3) 0.029(2) -0.002(2) 0.009(2) -0.004(2) C12 0.020(3) 0.049(3) 0.040(3) 0.008(2) 0.019(2) 0.001(2) C13 0.026(3) 0.033(3) 0.039(3) 0.006(2) 0.022(2) 0.005(2) N14 0.022(2) 0.026(2) 0.031(2) 0.0040(18) 0.0166(18) 0.0009(16) C15 0.025(3) 0.019(2) 0.036(3) -0.0051(19) 0.020(2) -0.0013(17) C16 0.046(3) 0.022(3) 0.065(4) 0.001(3) 0.041(3) 0.001(2) C17 0.079(7) 0.031(4) 0.083(7) -0.025(4) 0.062(6) -0.018(4) C18 0.042(3) 0.052(4) 0.071(5) -0.038(4) 0.038(4) -0.026(3) C19 0.026(3) 0.057(4) 0.038(3) -0.021(3) 0.016(3) -0.009(3) C20 0.026(2) 0.026(3) 0.033(3) -0.011(2) 0.017(2) -0.003(2) C21 0.033(3) 0.040(3) 0.037(3) 0.001(3) 0.017(3) 0.001(3) C22 0.073(6) 0.096(7) 0.100(7) -0.074(6) 0.054(6) -0.056(5) C23 0.074(7) 0.022(4) 0.092(7) 0.030(4) 0.050(6) 0.015(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.19082(8) loop_ _oxford_twin_element_scale_factors 0.475(8) 0.525(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Au1 . Cl2 . 2.2815(17) yes Au1 . C3 . 1.953(7) yes C3 . N4 . 1.373(7) yes C3 . N14 . 1.336(8) yes N4 . C5 . 1.462(7) yes N4 . C12 . 1.389(7) yes C5 . C6 . 1.513(8) yes C5 . H51 . 0.979 no C5 . H52 . 0.975 no C6 . C7 . 1.378(8) yes C6 . C11 . 1.397(7) yes C7 . C8 . 1.396(8) yes C7 . H71 . 0.944 no C8 . C9 . 1.392(9) yes C8 . H81 . 0.949 no C9 . C10 . 1.378(9) yes C9 . H91 . 0.895 no C10 . C11 . 1.370(8) yes C10 . H101 . 0.922 no C11 . H111 . 0.946 no C12 . C13 . 1.337(9) yes C12 . H121 . 0.928 no C13 . N14 . 1.380(6) yes C13 . H131 . 0.929 no N14 . C15 . 1.444(7) yes C15 . C16 . 1.405(7) yes C15 . C20 . 1.394(8) yes C16 . C17 . 1.397(11) yes C16 . C23 . 1.500(12) yes C17 . C18 . 1.354(14) yes C17 . H171 . 0.925 no C18 . C19 . 1.387(10) yes C18 . C22 . 1.520(9) yes C19 . C20 . 1.405(8) yes C19 . H191 . 0.937 no C20 . C21 . 1.495(8) yes C21 . H211 . 0.949 no C21 . H212 . 0.964 no C21 . H213 . 0.943 no C22 . H221 . 0.960 no C22 . H222 . 0.959 no C22 . H223 . 0.959 no C23 . H231 . 0.954 no C23 . H232 . 0.957 no C23 . H233 . 0.953 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl2 . Au1 . C3 . 178.7(2) yes Au1 . C3 . N4 . 126.7(5) yes Au1 . C3 . N14 . 130.0(4) yes N4 . C3 . N14 . 103.2(5) yes C3 . N4 . C5 . 125.8(5) yes C3 . N4 . C12 . 111.2(5) yes C5 . N4 . C12 . 122.8(5) yes N4 . C5 . C6 . 111.8(4) yes N4 . C5 . H51 . 108.6 no C6 . C5 . H51 . 109.6 no N4 . C5 . H52 . 108.4 no C6 . C5 . H52 . 109.5 no H51 . C5 . H52 . 108.8 no C5 . C6 . C7 . 120.4(5) yes C5 . C6 . C11 . 120.5(5) yes C7 . C6 . C11 . 119.1(5) yes C6 . C7 . C8 . 120.7(5) yes C6 . C7 . H71 . 118.4 no C8 . C7 . H71 . 120.9 no C7 . C8 . C9 . 119.5(5) yes C7 . C8 . H81 . 120.5 no C9 . C8 . H81 . 120.0 no C8 . C9 . C10 . 119.3(6) yes C8 . C9 . H91 . 120.2 no C10 . C9 . H91 . 120.5 no C9 . C10 . C11 . 121.3(6) yes C9 . C10 . H101 . 120.1 no C11 . C10 . H101 . 118.6 no C6 . C11 . C10 . 120.1(5) yes C6 . C11 . H111 . 119.0 no C10 . C11 . H111 . 120.9 no N4 . C12 . C13 . 106.3(5) yes N4 . C12 . H121 . 127.3 no C13 . C12 . H121 . 126.4 no C12 . C13 . N14 . 106.7(5) yes C12 . C13 . H131 . 127.0 no N14 . C13 . H131 . 126.4 no C13 . N14 . C3 . 112.6(5) yes C13 . N14 . C15 . 122.8(4) yes C3 . N14 . C15 . 124.6(4) yes N14 . C15 . C16 . 119.7(5) yes N14 . C15 . C20 . 117.9(4) yes C16 . C15 . C20 . 122.3(6) yes C15 . C16 . C17 . 117.7(7) yes C15 . C16 . C23 . 119.6(7) yes C17 . C16 . C23 . 122.7(8) yes C16 . C17 . C18 . 121.7(8) yes C16 . C17 . H171 . 118.6 no C18 . C17 . H171 . 119.7 no C17 . C18 . C19 . 119.8(6) yes C17 . C18 . C22 . 120.5(8) yes C19 . C18 . C22 . 119.7(9) yes C18 . C19 . C20 . 121.8(7) yes C18 . C19 . H191 . 119.0 no C20 . C19 . H191 . 119.2 no C19 . C20 . C15 . 116.7(5) yes C19 . C20 . C21 . 121.0(6) yes C15 . C20 . C21 . 122.2(5) yes C20 . C21 . H211 . 108.3 no C20 . C21 . H212 . 112.6 no H211 . C21 . H212 . 109.4 no C20 . C21 . H213 . 109.4 no H211 . C21 . H213 . 108.0 no H212 . C21 . H213 . 109.1 no C18 . C22 . H221 . 110.2 no C18 . C22 . H222 . 110.1 no H221 . C22 . H222 . 110.4 no C18 . C22 . H223 . 107.9 no H221 . C22 . H223 . 108.8 no H222 . C22 . H223 . 109.4 no C16 . C23 . H231 . 109.7 no C16 . C23 . H232 . 109.5 no H231 . C23 . H232 . 110.1 no C16 . C23 . H233 . 107.9 no H231 . C23 . H233 . 109.6 no H232 . C23 . H233 . 110.0 no