# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_address ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; _publ_contact_author_address ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; _publ_contact_author_email bettina.bechlars@ch.tum.de _publ_contact_author_fax '+49(0)89 289 13473' _publ_contact_author_phone '+49(0)89 289 13073' # end Validation Reply Form #=================================================================== # 1. SUBMISSION DETAILS #=================================================================== # Name and address of author for X-ray correspondence _publ_contact_author_name 'Dr. Bettina Bechlars' _publ_contact_letter # Include date of submission ; Date of submission: 12/21/2011 ; # Publication choise FI FM FO CI CM CO _publ_requested_category ? _publ_requested_coeditor_name ? #=================================================================== # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) #=================================================================== #=================================================================== # 3. TITLE AND AUTHOR LIST #=================================================================== _publ_section_title ; N-Heterocyclic Carbenes via Abstraction of Ammonia Filling a Gap: "Normal" Carbenes with "Abnormal" Character ; loop_ _publ_author_name L.-A.Schaper K.Ofele R.Kadyrov B.Bechlars M.Drees M.Cokoja ; W.Herrmann ; F.Kuhn data_2 _database_code_depnum_ccdc_archive 'CCDC 788089' #TrackingRef '2_jacs.cif' #=================================================================== # 0. AUDIT DETAILS _audit_creation_date 30-Juni-10 _audit_update_record ; 10-August-10 Updated by the Author B.B. 21-December-11 Updated by the Author L.-A.S. Text writing by B.B. Checkcif OK ; # start Validation Reply Form _vrf_PLAT374_2 ; PROBLEM: Long N - N Bond N1 - N2 ... 1.46 Ang. RESPONSE: This is a normal bond length for a single bond between two sp3 -hybridized nitrogen atoms. ; _vrf_PLAT035_2 ; PROBLEM: No _chemical_absolute_configuration info given . ? RESPONSE: Since there are no atoms in present that cause strong anomalous scattering the absolute configuration cannot be determined. Therefore the Friedel pairs have been merged for the refinement. ; #=================================================================== # 4. TEXT #=================================================================== _publ_section_abstract ; A new ammonia adduct of an N-heterocyclic carbene (NHC) has been isolated. It is shown that this type of NHC adduct can be used as reagent for the synthesis of transition metal carbene complexes. The new NHC ligand represents the first example of a 1,2,3-triazolylidene with a 1,2,4- substitution pattern, thus opening a new subclass ("normal" 1,2,3-triazol -ylidenes) of sterically and electronically tunable N-heterocyclic carbenes to serve as ligands in the quickly growing class of homogenous catalysts. ; # Insert blank lines between references _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). SIR92, J. Appl. Cryst. 27, 435-436. Farrugia, L. J. (1999). WinGX (Version 1.70.01 January 2005), J. Appl. Cryst. 32, 837-838. Sheldrick, G. M. (1998). SHELXL-97, University of G\"ottingen, G\"ottingen, Germany. Spek, A. L. (2008). PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. Stoe (2004). X-AREA, Version 1.26, Stoe & Cie GmbH, Darmstadt, Germany. ; #=================================================================== # 5. CHEMICAL DATA #=================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 N4' _chemical_formula_sum 'C16 H18 N4' _chemical_formula_weight 266.34 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' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M P212121 _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.4412(16) _cell_length_b 10.655(2) _cell_length_c 17.446(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1383.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9954 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 25.35 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9836 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator B. Bechlars scanspeed 10 s per frame dx 55 4552 frames measured in 6 data sets phi-scan with delta_phi = 0.5 omega-scans with delta_omega = 0.5 ; _publ_section_exptl_prep ; The crystal was coated with perfluoroplyether oil, mounted on a nylon loop and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Solution and refinements with the program WinGX; Farrugia (1999). Hydrogen atoms could not be located in the difference Fourier maps and were assigned to ideal positions (riding model). ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker APEX-II CCD ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 _diffrn_reflns_number 20485 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0241 _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 -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.42 _reflns_number_total 1484 _reflns_number_gt 1425 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2008)' _computing_publication_material 'PLATON (Spek, 2008)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _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^)+(0.0387P)^2^+0.1853P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -4(3) _refine_ls_number_reflns 1484 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.190 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.42 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.139 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.035 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== 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 N2 N 0.95629(19) 0.90707(13) 0.80802(8) 0.0232(3) Uani 1 1 d . . . N1 N 1.0566(2) 0.96903(13) 0.86893(8) 0.0243(3) Uani 1 1 d . . . N3 N 0.9147(2) 0.78532(13) 0.82896(8) 0.0224(3) Uani 1 1 d . . . C2 C 0.9990(2) 0.75810(15) 0.89122(10) 0.0214(4) Uani 1 1 d . . . C6 C 1.0020(2) 0.38203(17) 0.98027(11) 0.0274(4) Uani 1 1 d . . . C3 C 1.0003(2) 0.63000(16) 0.92262(10) 0.0215(4) Uani 1 1 d . . . C7 C 0.9242(3) 0.41060(16) 0.90987(11) 0.0272(4) Uani 1 1 d . . . N4 N 1.0601(3) 0.89405(15) 1.00253(9) 0.0303(4) Uani 1 1 d . . . C1 C 1.1033(2) 0.86762(16) 0.92364(10) 0.0237(4) Uani 1 1 d . . . C8 C 0.9231(2) 0.53138(16) 0.88117(10) 0.0247(4) Uani 1 1 d . . . C9 C 0.9999(3) 0.2505(2) 1.01171(15) 0.0376(5) Uani 1 1 d . . . C4 C 1.0792(3) 0.60249(17) 0.99296(11) 0.0280(4) Uani 1 1 d . . . C5 C 1.0807(3) 0.48015(18) 1.02079(11) 0.0304(4) Uani 1 1 d . . . C16 C 1.2159(3) 1.0296(2) 0.83575(12) 0.0342(5) Uani 1 1 d . . . C14 C 0.5713(3) 0.98943(18) 0.68441(11) 0.0311(4) Uani 1 1 d . . . C10 C 0.8144(2) 0.97756(16) 0.77433(10) 0.0220(4) Uani 1 1 d . . . C12 C 0.6681(3) 1.17438(17) 0.74917(11) 0.0321(4) Uani 1 1 d . . . C13 C 0.5541(3) 1.11815(19) 0.69741(11) 0.0314(4) Uani 1 1 d . . . C11 C 0.7989(3) 1.10551(18) 0.78781(10) 0.0274(4) Uani 1 1 d . . . C15 C 0.6993(3) 0.91935(17) 0.72238(11) 0.0274(4) Uani 1 1 d . . . H1 H 1.237(3) 0.8480(18) 0.9207(10) 0.021(5) Uiso 1 1 d . . . H2 H 0.943(4) 0.929(2) 1.0052(14) 0.050(7) Uiso 1 1 d . . . H3 H 1.136(4) 0.949(3) 1.0209(14) 0.052(7) Uiso 1 1 d . . . H4 H 1.127(3) 0.671(2) 1.0226(12) 0.031(6) Uiso 1 1 d . . . H5 H 1.132(3) 0.466(2) 1.0705(13) 0.041(6) Uiso 1 1 d . . . H6 H 0.874(3) 0.346(2) 0.8772(13) 0.039(6) Uiso 1 1 d . . . H7 H 0.868(3) 0.5476(18) 0.8302(11) 0.026(5) Uiso 1 1 d . . . H8 H 1.013(4) 0.188(3) 0.9769(18) 0.075(10) Uiso 1 1 d . . . H9 H 1.094(5) 0.239(3) 1.054(2) 0.095(11) Uiso 1 1 d . . . H10 H 0.896(5) 0.236(3) 1.0378(18) 0.082(11) Uiso 1 1 d . . . H11 H 0.873(3) 1.145(2) 0.8258(13) 0.042(6) Uiso 1 1 d . . . H12 H 0.662(3) 1.264(2) 0.7612(12) 0.040(6) Uiso 1 1 d . . . H13 H 0.460(3) 1.168(2) 0.6706(12) 0.033(5) Uiso 1 1 d . . . H14 H 0.490(3) 0.948(2) 0.6486(12) 0.032(5) Uiso 1 1 d . . . H15 H 0.716(3) 0.829(2) 0.7129(13) 0.044(6) Uiso 1 1 d . . . H16 H 1.172(3) 1.099(2) 0.7991(14) 0.049(7) Uiso 1 1 d . . . H17 H 1.277(3) 1.071(2) 0.8785(13) 0.038(6) Uiso 1 1 d . . . H18 H 1.294(4) 0.970(2) 0.8104(14) 0.053(7) Uiso 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 N2 0.0259(8) 0.0200(7) 0.0235(7) 0.0000(6) -0.0039(6) -0.0026(6) N1 0.0267(8) 0.0236(7) 0.0226(7) -0.0004(6) -0.0027(6) -0.0054(6) N3 0.0248(7) 0.0192(6) 0.0233(7) 0.0009(6) 0.0009(7) 0.0002(6) C2 0.0204(8) 0.0227(8) 0.0211(8) -0.0018(6) 0.0022(7) 0.0006(7) C6 0.0227(8) 0.0261(9) 0.0335(10) 0.0060(8) 0.0040(8) 0.0048(8) C3 0.0191(8) 0.0228(8) 0.0227(8) 0.0008(7) 0.0034(7) 0.0023(7) C7 0.0264(9) 0.0242(8) 0.0311(10) -0.0025(7) 0.0023(8) 0.0004(8) N4 0.0395(9) 0.0272(8) 0.0243(8) -0.0028(7) -0.0065(8) -0.0007(8) C1 0.0223(9) 0.0225(8) 0.0263(9) 0.0012(7) -0.0026(7) -0.0012(7) C8 0.0253(8) 0.0259(8) 0.0228(9) -0.0005(7) 0.0011(8) 0.0024(8) C9 0.0365(11) 0.0295(10) 0.0468(13) 0.0105(10) 0.0007(11) 0.0027(9) C4 0.0267(8) 0.0287(9) 0.0284(9) -0.0002(8) -0.0045(8) 0.0006(8) C5 0.0287(9) 0.0337(9) 0.0288(10) 0.0062(8) -0.0036(8) 0.0022(9) C16 0.0356(11) 0.0341(10) 0.0328(11) 0.0028(9) -0.0022(9) -0.0156(9) C14 0.0283(9) 0.0335(9) 0.0316(10) 0.0036(8) -0.0051(9) -0.0016(8) C10 0.0217(8) 0.0240(8) 0.0204(8) 0.0027(7) 0.0035(7) -0.0002(7) C12 0.0407(11) 0.0239(9) 0.0319(10) 0.0029(8) 0.0022(9) 0.0053(8) C13 0.0298(10) 0.0334(9) 0.0311(10) 0.0097(8) -0.0009(8) 0.0056(9) C11 0.0338(9) 0.0259(9) 0.0227(9) 0.0002(7) 0.0007(8) 0.0001(8) C15 0.0280(9) 0.0241(8) 0.0301(9) 0.0010(7) -0.0020(8) -0.0009(7) _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. ; #=================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== 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 N2 N3 1.383(2) . ? N2 C10 1.423(2) . ? N2 N1 1.457(2) . ? N1 C16 1.468(2) . ? N1 C1 1.483(2) . ? N3 C2 1.287(2) . ? C2 C3 1.471(2) . ? C2 C1 1.511(2) . ? C6 C5 1.391(3) . ? C6 C7 1.391(3) . ? C6 C9 1.505(3) . ? C3 C4 1.392(2) . ? C3 C8 1.399(3) . ? C7 C8 1.381(2) . ? C7 H6 0.97(2) . ? N4 C1 1.441(2) . ? N4 H2 0.95(3) . ? N4 H3 0.88(3) . ? C1 H1 1.02(2) . ? C8 H7 0.99(2) . ? C9 H8 0.91(3) . ? C9 H9 1.03(4) . ? C9 H10 0.91(3) . ? C4 C5 1.391(3) . ? C4 H4 0.96(2) . ? C5 H5 0.96(2) . ? C16 H16 1.03(2) . ? C16 H17 0.98(2) . ? C16 H18 0.97(3) . ? C14 C15 1.379(3) . ? C14 C13 1.396(3) . ? C14 H14 0.97(2) . ? C10 C11 1.388(2) . ? C10 C15 1.393(3) . ? C12 C13 1.376(3) . ? C12 C11 1.393(3) . ? C12 H12 0.97(2) . ? C13 H13 1.00(2) . ? C11 H11 0.96(2) . ? C15 H15 0.98(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 N3 N2 C10 116.00(14) . . ? N3 N2 N1 110.31(12) . . ? C10 N2 N1 116.25(13) . . ? N2 N1 C16 108.98(14) . . ? N2 N1 C1 105.03(12) . . ? C16 N1 C1 112.64(15) . . ? C2 N3 N2 108.98(14) . . ? N3 C2 C3 121.77(15) . . ? N3 C2 C1 113.08(15) . . ? C3 C2 C1 125.02(15) . . ? C5 C6 C7 117.34(17) . . ? C5 C6 C9 121.27(18) . . ? C7 C6 C9 121.39(18) . . ? C4 C3 C8 118.09(16) . . ? C4 C3 C2 121.77(16) . . ? C8 C3 C2 120.13(16) . . ? C8 C7 C6 121.76(18) . . ? C8 C7 H6 116.6(13) . . ? C6 C7 H6 121.5(13) . . ? C1 N4 H2 109.1(15) . . ? C1 N4 H3 109.6(17) . . ? H2 N4 H3 108(2) . . ? N4 C1 N1 114.83(14) . . ? N4 C1 C2 113.19(15) . . ? N1 C1 C2 101.62(13) . . ? N4 C1 H1 107.8(10) . . ? N1 C1 H1 110.3(11) . . ? C2 C1 H1 108.9(11) . . ? C7 C8 C3 120.68(17) . . ? C7 C8 H7 119.3(12) . . ? C3 C8 H7 120.0(12) . . ? C6 C9 H8 116(2) . . ? C6 C9 H9 111(2) . . ? H8 C9 H9 109(3) . . ? C6 C9 H10 110(2) . . ? H8 C9 H10 108(3) . . ? H9 C9 H10 102(3) . . ? C5 C4 C3 120.55(18) . . ? C5 C4 H4 121.5(12) . . ? C3 C4 H4 117.8(12) . . ? C4 C5 C6 121.57(18) . . ? C4 C5 H5 117.9(14) . . ? C6 C5 H5 120.4(14) . . ? N1 C16 H16 107.9(14) . . ? N1 C16 H17 105.8(14) . . ? H16 C16 H17 106.9(18) . . ? N1 C16 H18 112.0(15) . . ? H16 C16 H18 112(2) . . ? H17 C16 H18 112(2) . . ? C15 C14 C13 121.13(19) . . ? C15 C14 H14 119.6(12) . . ? C13 C14 H14 119.3(13) . . ? C11 C10 C15 119.74(17) . . ? C11 C10 N2 120.69(16) . . ? C15 C10 N2 119.36(15) . . ? C13 C12 C11 121.25(17) . . ? C13 C12 H12 122.4(13) . . ? C11 C12 H12 116.4(14) . . ? C12 C13 C14 118.55(18) . . ? C12 C13 H13 120.5(12) . . ? C14 C13 H13 120.9(12) . . ? C10 C11 C12 119.59(18) . . ? C10 C11 H11 120.1(14) . . ? C12 C11 H11 120.2(14) . . ? C14 C15 C10 119.74(17) . . ? C14 C15 H15 122.4(14) . . ? C10 C15 H15 117.9(14) . . ? # End of Crystallographic Information File # Attachment '4_jacs.cif' # CIF-file generated for ScAr13 # Compound 4 #=================================================================== data_4 _database_code_depnum_ccdc_archive 'CCDC 797025' #TrackingRef '4_jacs.cif' #=================================================================== # 0. AUDIT DETAILS _audit_creation_date 16-September-10 _audit_update_record ; 16-September-10 Updated by the Author B.B. 21-December-11 Updated by the Author L.-A.S. Text writing by B.B. Checkcif OK ; #=================================================================== # 4. TEXT #=================================================================== _publ_section_abstract ; A new ammonia adduct of an N-heterocyclic carbene (NHC) has been isolated. It is shown that this type of NHC adduct can be used as reagent for the synthesis of transition metal carbene complexes. The new NHC ligand represents the first example of a 1,2,3-triazolylidene with a 1,2,4- substitution pattern, thus opening a new subclass ("normal" 1,2,3-triazol- ylidenes) of sterically and electronically tunable N-heterocyclic carbenes to serve as ligands in the quickly growing class of homogenous catalysts. ; # Insert blank lines between references _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). SIR92, J. Appl. Cryst. 27, 435-436. Farrugia, L. J. (1999). WinGX (Version 1.70.01 January 2005), J. Appl. Cryst. 32, 837-838. Sheldrick, G. M. (1998). SHELXL-97, University of G\"ottingen, G\"ottingen, Germany. Spek, A. L. (2008). PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. Stoe (2004). X-AREA, Version 1.26, Stoe & Cie GmbH, Darmstadt, Germany. ; #=================================================================== # 5. CHEMICAL DATA #=================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H15 Cl Ir N3 O2' _chemical_formula_sum 'C18 H15 Cl Ir N3 O2' _chemical_formula_weight 532.98 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' Ir Ir -1.4442 7.9887 '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' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M P21/c _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 7.5266(9) _cell_length_b 22.640(3) _cell_length_c 11.6560(15) _cell_angle_alpha 90.00 _cell_angle_beta 114.720(8) _cell_angle_gamma 90.00 _cell_volume 1804.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7014 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 25.15 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.962 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 7.564 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5829 _exptl_absorpt_correction_T_max 0.7036 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator B. Bechlars scanspeed 10 s per frame dx 55 2448 frames measured in 6 data sets phi-scan with delta_phi = 0.5 omega-scans with delta_omega = 0.5 ; _publ_section_exptl_prep ; The crystal was coated with perfluoroplyether oil, mounted on a nylon loop and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Solution and refinements with the program WinGX; Farrugia (1999). Hydrogen atoms could not be located in the difference Fourier maps and were assigned to ideal positions (riding model). ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker APEX-II CCD ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 _diffrn_reflns_number 18809 _diffrn_reflns_av_R_equivalents 0.0792 _diffrn_reflns_av_sigmaI/netI 0.0667 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.44 _reflns_number_total 3247 _reflns_number_gt 2545 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2008)' _computing_publication_material 'PLATON (Spek, 2008)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _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. ; _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^)+(0.0542P)^2^+4.9502P] 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 3247 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1161 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.44 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 2.401 _refine_diff_density_min -1.973 _refine_diff_density_rms 0.233 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== 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 Ir1 Ir 0.43116(5) 0.235709(13) 0.48456(3) 0.02774(16) Uani 1 1 d . . . Cl1 Cl 0.2197(4) 0.25004(11) 0.5861(2) 0.0416(6) Uani 1 1 d . . . O1 O 0.5176(10) 0.1133(3) 0.6058(6) 0.0481(17) Uani 1 1 d . . . O2 O 0.6973(10) 0.2205(3) 0.3527(6) 0.0476(17) Uani 1 1 d . . . N1 N 0.1753(10) 0.3350(3) 0.3158(6) 0.0299(16) Uani 1 1 d . . . N2 N 0.1814(10) 0.3915(3) 0.2721(6) 0.0308(16) Uani 1 1 d . . . N3 N 0.3623(11) 0.4134(3) 0.3278(6) 0.0327(17) Uani 1 1 d . . . C1 C 0.3577(12) 0.3197(4) 0.4019(7) 0.0286(19) Uani 1 1 d . . . C2 C 0.4721(12) 0.3712(4) 0.4081(7) 0.0284(19) Uani 1 1 d . . . C3 C 0.6825(12) 0.3803(3) 0.4842(8) 0.030(2) Uani 1 1 d . . . C4 C 0.7840(14) 0.3548(4) 0.6046(8) 0.035(2) Uani 1 1 d . . . H4 H 0.7139 0.3318 0.6401 0.042 Uiso 1 1 calc R . . C5 C 0.9860(13) 0.3626(4) 0.6730(9) 0.034(2) Uani 1 1 d . . . H5 H 1.0500 0.3446 0.7537 0.041 Uiso 1 1 calc R . . C6 C 1.0953(12) 0.3962(4) 0.6248(8) 0.031(2) Uani 1 1 d . . . C7 C 0.9924(14) 0.4226(4) 0.5042(8) 0.037(2) Uani 1 1 d . . . H7 H 1.0627 0.4458 0.4692 0.044 Uiso 1 1 calc R . . C8 C 0.7926(13) 0.4154(4) 0.4363(8) 0.033(2) Uani 1 1 d . . . H8 H 0.7283 0.4343 0.3567 0.040 Uiso 1 1 calc R . . C9 C 1.3137(14) 0.4025(4) 0.6939(9) 0.045(2) Uani 1 1 d . . . H9A H 1.3572 0.3861 0.7791 0.068 Uiso 1 1 calc R . . H9B H 1.3491 0.4444 0.6995 0.068 Uiso 1 1 calc R . . H9C H 1.3770 0.3812 0.6480 0.068 Uiso 1 1 calc R . . C10 C 0.0258(13) 0.4203(4) 0.1682(8) 0.032(2) Uani 1 1 d . . . C11 C -0.0398(13) 0.4753(4) 0.1859(8) 0.035(2) Uani 1 1 d . . . H11 H 0.0117 0.4931 0.2672 0.042 Uiso 1 1 calc R . . C12 C -0.1810(14) 0.5040(4) 0.0837(9) 0.043(2) Uani 1 1 d . . . H12 H -0.2243 0.5421 0.0947 0.051 Uiso 1 1 calc R . . C13 C -0.2606(14) 0.4776(4) -0.0349(9) 0.039(2) Uani 1 1 d . . . H13 H -0.3600 0.4972 -0.1041 0.047 Uiso 1 1 calc R . . C14 C -0.1937(14) 0.4224(4) -0.0517(9) 0.039(2) Uani 1 1 d . . . H14 H -0.2465 0.4047 -0.1331 0.047 Uiso 1 1 calc R . . C15 C -0.0508(13) 0.3927(4) 0.0489(8) 0.036(2) Uani 1 1 d . . . H15 H -0.0060 0.3548 0.0377 0.043 Uiso 1 1 calc R . . C16 C -0.0122(12) 0.3023(4) 0.2736(8) 0.033(2) Uani 1 1 d . . . H16A H 0.0012 0.2702 0.3330 0.050 Uiso 1 1 calc R . . H16B H -0.0460 0.2859 0.1893 0.050 Uiso 1 1 calc R . . H16C H -0.1158 0.3293 0.2707 0.050 Uiso 1 1 calc R . . C17 C 0.4896(12) 0.1597(4) 0.5600(8) 0.031(2) Uani 1 1 d . . . C18 C 0.5858(14) 0.2264(4) 0.3999(8) 0.034(2) 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 Ir1 0.0335(3) 0.0204(2) 0.0335(2) 0.00159(14) 0.01815(19) 0.00031(14) Cl1 0.0542(16) 0.0350(11) 0.0496(14) 0.0021(11) 0.0354(13) 0.0008(12) O1 0.062(5) 0.027(4) 0.063(4) 0.014(3) 0.033(4) 0.006(3) O2 0.051(4) 0.043(4) 0.062(4) 0.008(3) 0.037(4) 0.011(3) N1 0.043(5) 0.022(4) 0.033(4) 0.000(3) 0.024(4) -0.001(3) N2 0.036(4) 0.022(4) 0.036(4) 0.005(3) 0.016(4) 0.003(3) N3 0.038(5) 0.026(4) 0.036(4) 0.002(3) 0.018(4) 0.001(3) C1 0.034(5) 0.029(5) 0.026(4) -0.002(4) 0.015(4) 0.005(4) C2 0.034(5) 0.026(4) 0.030(4) 0.004(4) 0.018(4) 0.003(4) C3 0.036(5) 0.019(4) 0.041(5) -0.001(4) 0.022(4) 0.004(4) C4 0.045(6) 0.026(5) 0.046(5) 0.001(4) 0.029(5) 0.003(4) C5 0.039(6) 0.028(5) 0.041(5) 0.000(4) 0.021(5) 0.004(4) C6 0.030(5) 0.022(4) 0.040(5) -0.007(4) 0.015(4) 0.001(4) C7 0.041(6) 0.031(5) 0.042(5) -0.005(4) 0.021(5) -0.006(5) C8 0.035(5) 0.028(5) 0.036(5) 0.004(4) 0.015(4) 0.002(4) C9 0.047(6) 0.040(6) 0.047(6) -0.009(5) 0.018(5) -0.012(5) C10 0.031(5) 0.028(5) 0.045(5) 0.013(4) 0.024(4) 0.005(4) C11 0.048(6) 0.025(4) 0.039(5) 0.008(4) 0.025(5) 0.008(4) C12 0.059(6) 0.025(5) 0.060(7) 0.005(5) 0.040(6) 0.004(5) C13 0.040(6) 0.035(5) 0.047(6) 0.010(5) 0.022(5) -0.002(4) C14 0.040(6) 0.036(5) 0.039(5) -0.001(4) 0.016(5) -0.006(5) C15 0.039(5) 0.030(5) 0.042(5) 0.001(4) 0.021(5) -0.004(4) C16 0.026(5) 0.026(5) 0.051(5) 0.000(4) 0.020(4) -0.006(4) C17 0.026(5) 0.038(5) 0.032(5) -0.003(4) 0.016(4) 0.005(4) C18 0.037(6) 0.021(4) 0.032(5) -0.004(4) 0.002(4) -0.013(4) #=================================================================== # 10. 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 Ir1 C18 1.826(10) . ? Ir1 C17 1.899(9) . ? Ir1 C1 2.098(8) . ? Ir1 Cl1 2.369(2) . ? O1 C17 1.156(10) . ? O2 C18 1.188(11) . ? N1 C1 1.364(10) . ? N1 N2 1.386(9) . ? N1 C16 1.483(10) . ? N2 N3 1.335(9) . ? N2 C10 1.441(11) . ? N3 C2 1.351(10) . ? C1 C2 1.434(11) . ? C2 C3 1.471(12) . ? C3 C4 1.410(12) . ? C3 C8 1.421(11) . ? C4 C5 1.401(12) . ? C4 H4 0.9500 . ? C5 C6 1.400(11) . ? C5 H5 0.9500 . ? C6 C7 1.423(12) . ? C6 C9 1.505(12) . ? C7 C8 1.385(13) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.387(11) . ? C10 C15 1.410(12) . ? C11 C12 1.382(12) . ? C11 H11 0.9500 . ? C12 C13 1.390(13) . ? C12 H12 0.9500 . ? C13 C14 1.393(13) . ? C13 H13 0.9500 . ? C14 C15 1.389(12) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 C18 Ir1 C17 94.0(4) . . ? C18 Ir1 C1 87.8(3) . . ? C17 Ir1 C1 178.1(3) . . ? C18 Ir1 Cl1 177.3(3) . . ? C17 Ir1 Cl1 88.1(2) . . ? C1 Ir1 Cl1 90.1(2) . . ? C1 N1 N2 109.1(7) . . ? C1 N1 C16 130.0(7) . . ? N2 N1 C16 120.8(7) . . ? N3 N2 N1 110.4(6) . . ? N3 N2 C10 123.1(7) . . ? N1 N2 C10 125.9(7) . . ? N2 N3 C2 106.1(7) . . ? N1 C1 C2 103.2(7) . . ? N1 C1 Ir1 124.0(6) . . ? C2 C1 Ir1 132.6(6) . . ? N3 C2 C1 111.1(7) . . ? N3 C2 C3 120.7(7) . . ? C1 C2 C3 128.1(7) . . ? C4 C3 C8 117.3(8) . . ? C4 C3 C2 122.8(7) . . ? C8 C3 C2 120.0(7) . . ? C5 C4 C3 121.5(8) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C6 C5 C4 121.3(8) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 117.2(8) . . ? C5 C6 C9 122.1(8) . . ? C7 C6 C9 120.7(8) . . ? C8 C7 C6 121.9(8) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C3 120.9(8) . . ? C7 C8 H8 119.6 . . ? C3 C8 H8 119.6 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 121.4(8) . . ? C11 C10 N2 119.7(8) . . ? C15 C10 N2 118.8(7) . . ? C12 C11 C10 119.1(9) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 120.8(9) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C14 119.6(9) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.9(9) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C10 118.1(8) . . ? C14 C15 H15 121.0 . . ? C10 C15 H15 121.0 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O1 C17 Ir1 177.2(7) . . ? O2 C18 Ir1 175.4(8) . . ? # End of Crystallographic Information File # Attachment '3_jacs.cif' # CIF-file generated for ScAr12 # Compound 3 #=================================================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 797026' #TrackingRef '3_jacs.cif' #=================================================================== # 0. AUDIT DETAILS _audit_creation_date 16-September-10 _audit_update_record ; 16-September-10 Updated by the Author B.B. 21-December-11 Updated by the Author L.-A.S. Text writing by B.B. Checkcif OK ; #=================================================================== # 4. TEXT #=================================================================== _publ_section_abstract ; A new ammonia adduct of an N-heterocyclic carbene (NHC) has been isolated. It is shown that this type of NHC adduct can be used as reagent for the synthesis of transition metal carbene complexes. The new NHC ligand represents the first example of a 1,2,3-triazolylidene with a 1,2,4- substitution pattern, thus opening a new subclass ("normal" 1,2,3-triazol- ylidenes) of sterically and electronically tunable N-heterocyclic carbenes to serve as ligands in the quickly growing class of homogenous catalysts. ; # Insert blank lines between references _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). SIR92, J. Appl. Cryst. 27, 435-436. Farrugia, L. J. (1999). WinGX (Version 1.70.01 January 2005), J. Appl. Cryst. 32, 837-838. Sheldrick, G. M. (1998). SHELXL-97, University of G\"ottingen, G\"ottingen, Germany. Spek, A. L. (2008). PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. Stoe (2004). X-AREA, Version 1.26, Stoe & Cie GmbH, Darmstadt, Germany. ; #=================================================================== # 5. CHEMICAL DATA #=================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3' _chemical_formula_sum 'C15 H13 N3' _chemical_formula_weight 235.28 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' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M P21/c _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 13.034(4) _cell_length_b 5.507(2) _cell_length_c 18.643(6) _cell_angle_alpha 90 _cell_angle_beta 106.30(2) _cell_angle_gamma 90 _cell_volume 1284.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1405 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 23.33 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9757 _exptl_absorpt_correction_T_max 0.9985 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator B. Bechlars scanspeed 20 s per frame dx 55 3044 frames measured in 8 data sets phi-scan with delta_phi = 0.5 omega-scans with delta_omega = 0.5 ; _publ_section_exptl_prep ; The crystal was coated with perfluoroplyether oil, mounted on a nylon loop and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Solution and refinements with the program WinGX; Farrugia (1999). Hydrogen atoms could not be located in the difference Fourier maps and were assigned to ideal positions (riding model). ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker APEX-II CCD ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 _diffrn_reflns_number 12071 _diffrn_reflns_av_R_equivalents 0.1064 _diffrn_reflns_av_sigmaI/netI 0.1068 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 22.35 _reflns_number_total 1538 _reflns_number_gt 973 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2008)' _computing_publication_material 'PLATON (Spek, 2008)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _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. ; _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^)+(0.0564P)^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 1538 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1082 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1521 _refine_ls_wR_factor_gt 0.1311 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 22.35 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.181 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.049 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== 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 N3 N 0.2922(2) 0.0826(4) 0.93525(15) 0.0343(8) Uani 1 1 d . . . N2 N 0.3628(2) 0.0843(4) 1.00353(14) 0.0371(8) Uani 1 1 d . . . H1 H 0.4139 0.1942 1.0146 0.044 Uiso 1 1 calc R . . C9 C 0.0018(3) 0.2399(5) 0.58631(18) 0.0517(11) Uani 1 1 d . . . H6 H -0.0498 0.3730 0.5805 0.078 Uiso 1 1 calc R . . H8 H -0.0364 0.0846 0.5778 0.078 Uiso 1 1 calc R . . H7 H 0.0429 0.2592 0.5500 0.078 Uiso 1 1 calc R . . C6 C 0.0770(3) 0.2444(5) 0.66456(18) 0.0383(9) Uani 1 1 d . . . C5 C 0.1514(3) 0.4298(5) 0.68783(19) 0.0389(10) Uani 1 1 d . . . H3 H 0.1545 0.5570 0.6541 0.047 Uiso 1 1 calc R . . C4 C 0.2216(3) 0.4330(5) 0.75982(19) 0.0369(9) Uani 1 1 d . . . H2 H 0.2710 0.5630 0.7745 0.044 Uiso 1 1 calc R . . C3 C 0.2201(3) 0.2470(4) 0.81046(17) 0.0322(9) Uani 1 1 d . . . C2 C 0.2970(2) 0.2487(5) 0.88622(18) 0.0334(9) Uani 1 1 d . . . C10 C 0.3553(3) -0.0887(5) 1.05700(18) 0.0311(9) Uani 1 1 d . . . C15 C 0.2840(2) -0.2859(5) 1.03953(18) 0.0363(9) Uani 1 1 d . . . H13 H 0.2387 -0.3047 0.9901 0.044 Uiso 1 1 calc R . . C14 C 0.2796(3) -0.4519(5) 1.09406(19) 0.0380(10) Uani 1 1 d . . . H12 H 0.2316 -0.5852 1.0817 0.046 Uiso 1 1 calc R . . C13 C 0.3448(3) -0.4267(5) 1.1670(2) 0.0404(10) Uani 1 1 d . . . H11 H 0.3408 -0.5404 1.2045 0.048 Uiso 1 1 calc R . . C7 C 0.0754(3) 0.0592(5) 0.71567(19) 0.0383(9) Uani 1 1 d . . . H4 H 0.0251 -0.0691 0.7011 0.046 Uiso 1 1 calc R . . C8 C 0.1455(3) 0.0588(5) 0.78705(19) 0.0366(9) Uani 1 1 d . . . H5 H 0.1431 -0.0700 0.8204 0.044 Uiso 1 1 calc R . . C11 C 0.4214(3) -0.0653(5) 1.12991(18) 0.0354(9) Uani 1 1 d . . . H9 H 0.4705 0.0659 1.1424 0.042 Uiso 1 1 calc R . . C12 C 0.4156(3) -0.2327(5) 1.18415(19) 0.0403(10) Uani 1 1 d . . . H10 H 0.4606 -0.2146 1.2337 0.048 Uiso 1 1 calc R . . C1 C 0.3783(3) 0.4388(5) 0.90355(16) 0.0332(9) Uani 1 1 d . . . N1 N 0.4428(2) 0.5888(5) 0.91935(15) 0.0448(9) 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 N3 0.035(2) 0.0296(14) 0.0371(19) -0.0013(13) 0.0082(16) 0.0007(12) N2 0.040(2) 0.0288(14) 0.041(2) 0.0023(13) 0.0096(17) -0.0074(12) C9 0.047(3) 0.061(2) 0.046(3) -0.0020(18) 0.011(2) 0.0096(18) C6 0.036(3) 0.0418(19) 0.036(2) -0.0052(16) 0.0083(19) 0.0090(15) C5 0.048(3) 0.0321(17) 0.040(2) 0.0052(15) 0.017(2) 0.0053(15) C4 0.040(3) 0.0297(16) 0.042(2) -0.0027(15) 0.014(2) -0.0017(14) C3 0.032(2) 0.0262(16) 0.039(2) -0.0011(15) 0.0120(19) 0.0033(14) C2 0.039(3) 0.0231(16) 0.042(2) 0.0005(15) 0.017(2) -0.0012(14) C10 0.031(2) 0.0262(16) 0.036(2) 0.0021(14) 0.0096(19) 0.0048(14) C15 0.032(2) 0.0324(16) 0.044(2) -0.0023(16) 0.0104(18) -0.0008(14) C14 0.035(3) 0.0293(16) 0.051(3) 0.0006(16) 0.015(2) -0.0024(14) C13 0.045(3) 0.0331(18) 0.049(3) 0.0098(16) 0.023(2) 0.0081(16) C7 0.036(3) 0.0365(18) 0.043(2) -0.0080(16) 0.012(2) -0.0024(14) C8 0.041(3) 0.0292(16) 0.043(2) -0.0009(15) 0.016(2) -0.0011(15) C11 0.034(2) 0.0269(16) 0.044(3) 0.0017(15) 0.010(2) -0.0007(13) C12 0.043(3) 0.0347(18) 0.043(2) -0.0004(16) 0.0124(19) 0.0028(15) C1 0.038(3) 0.0326(17) 0.031(2) 0.0047(15) 0.0137(18) 0.0076(17) N1 0.051(2) 0.0370(16) 0.046(2) -0.0002(13) 0.0129(17) -0.0068(15) #=================================================================== # 10. 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 N3 C2 1.307(3) . ? N3 N2 1.345(3) . ? N2 C10 1.402(4) . ? N2 H1 0.8800 . ? C9 C6 1.512(4) . ? C9 H6 0.9800 . ? C9 H8 0.9800 . ? C9 H7 0.9800 . ? C6 C5 1.391(4) . ? C6 C7 1.400(4) . ? C5 C4 1.396(4) . ? C5 H3 0.9500 . ? C4 C3 1.397(4) . ? C4 H2 0.9500 . ? C3 C8 1.404(4) . ? C3 C2 1.485(4) . ? C2 C1 1.459(5) . ? C10 C11 1.396(4) . ? C10 C15 1.407(4) . ? C15 C14 1.380(4) . ? C15 H13 0.9500 . ? C14 C13 1.394(4) . ? C14 H12 0.9500 . ? C13 C12 1.389(4) . ? C13 H11 0.9500 . ? C7 C8 1.387(4) . ? C7 H4 0.9500 . ? C8 H5 0.9500 . ? C11 C12 1.386(4) . ? C11 H9 0.9500 . ? C12 H10 0.9500 . ? C1 N1 1.157(4) . ? 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 N3 N2 120.1(3) . . ? N3 N2 C10 120.1(2) . . ? N3 N2 H1 119.9 . . ? C10 N2 H1 119.9 . . ? C6 C9 H6 109.5 . . ? C6 C9 H8 109.5 . . ? H6 C9 H8 109.5 . . ? C6 C9 H7 109.5 . . ? H6 C9 H7 109.5 . . ? H8 C9 H7 109.5 . . ? C5 C6 C7 117.7(3) . . ? C5 C6 C9 121.3(3) . . ? C7 C6 C9 121.0(3) . . ? C6 C5 C4 121.4(3) . . ? C6 C5 H3 119.3 . . ? C4 C5 H3 119.3 . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H2 119.6 . . ? C3 C4 H2 119.6 . . ? C4 C3 C8 118.1(3) . . ? C4 C3 C2 120.3(3) . . ? C8 C3 C2 121.6(3) . . ? N3 C2 C1 121.4(3) . . ? N3 C2 C3 120.6(3) . . ? C1 C2 C3 118.0(3) . . ? C11 C10 N2 118.9(3) . . ? C11 C10 C15 118.9(3) . . ? N2 C10 C15 122.2(3) . . ? C14 C15 C10 120.1(3) . . ? C14 C15 H13 119.9 . . ? C10 C15 H13 119.9 . . ? C15 C14 C13 120.9(3) . . ? C15 C14 H12 119.6 . . ? C13 C14 H12 119.6 . . ? C12 C13 C14 119.0(3) . . ? C12 C13 H11 120.5 . . ? C14 C13 H11 120.5 . . ? C8 C7 C6 121.5(3) . . ? C8 C7 H4 119.2 . . ? C6 C7 H4 119.2 . . ? C7 C8 C3 120.6(3) . . ? C7 C8 H5 119.7 . . ? C3 C8 H5 119.7 . . ? C12 C11 C10 120.3(3) . . ? C12 C11 H9 119.9 . . ? C10 C11 H9 119.9 . . ? C11 C12 C13 120.8(3) . . ? C11 C12 H10 119.6 . . ? C13 C12 H10 119.6 . . ? N1 C1 C2 178.1(3) . . ? # End of Crystallographic Information File # Attachment '5a_jacs.cif' # CIF-file generated for ScAr17 # Compound 5a #=================================================================== data_5a _database_code_depnum_ccdc_archive 'CCDC 849440' #TrackingRef '5a_jacs.cif' #=================================================================== # 0. AUDIT DETAILS _audit_creation_date 28-April-11 _audit_update_record ; 28-April-11 Updated by the Author B.B. 21-December-11 Updated by the Author L.-A.S. Text writing by B.B. Checkcif OK ; #=================================================================== # 4. TEXT #=================================================================== _publ_section_abstract ; A new ammonia adduct of an N-heterocyclic carbene (NHC) has been isolated. It is shown that this type of NHC adduct can be used as reagent for the synthesis of transition metal carbene complexes. The new NHC ligand represents the first example of a 1,2,3-triazolylidene with a 1,2,4- substitution pattern, thus opening a new subclass ("normal" 1,2,3-triazol- ylidenes) of sterically and electronically tunable N-heterocyclic carbenes to serve as ligands in the quickly growing class of homogenous catalysts. ; # Insert blank lines between references _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). SIR92, J. Appl. Cryst. 27, 435-436. Farrugia, L. J. (1999). WinGX (Version 1.70.01 January 2005), J. Appl. Cryst. 32, 837-838. Sheldrick, G. M. (1998). SHELXL-97, University of G\"ottingen, G\"ottingen, Germany. Spek, A. L. (2008). PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. Stoe (2004). X-AREA, Version 1.26, Stoe & Cie GmbH, Darmstadt, Germany. ; #=================================================================== # 5. CHEMICAL DATA #=================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H15 Au Cl N3' _chemical_formula_sum 'C16 H15 Au Cl N3' _chemical_formula_weight 481.73 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' Au Au -2.0133 8.8022 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M P-1 _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7486(4) _cell_length_b 11.6907(8) _cell_length_c 12.9093(9) _cell_angle_alpha 67.988(3) _cell_angle_beta 87.564(3) _cell_angle_gamma 78.131(3) _cell_volume 786.56(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7633 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 25.32 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.034 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 9.517 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0969 _exptl_absorpt_correction_T_max 0.6476 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator B. Bechlars scanspeed 15 s per frame dx 40 3284 frames measured in 7 data sets phi-scan with delta_phi = 0.5 omega-scans with delta_omega = 0.5 ; _publ_section_exptl_prep ; The crystal was coated with perfluoroplyether oil, mounted on a glass capillary and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Solution and refinements with the program WinGX; Farrugia (1999). Hydrogen atoms could not be located in the difference Fourier maps and were assigned to ideal positions (riding model). ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _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 ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker APEX-II CCD ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 _diffrn_reflns_number 12020 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.33 _reflns_number_total 2833 _reflns_number_gt 2571 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2008)' _computing_publication_material 'PLATON (Spek, 2008)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _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. ; _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^)+(0.0527P)^2^+0.4083P] 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 2833 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0728 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 2.091 _refine_diff_density_min -1.184 _refine_diff_density_rms 0.166 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== 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 1.0037(11) -0.0160(5) 0.1910(5) 0.0298(13) Uani 1 1 d . . . C2 C 0.8236(10) -0.0159(5) 0.2678(4) 0.0283(12) Uani 1 1 d . . . C3 C 0.6674(11) -0.1071(5) 0.3172(5) 0.0305(13) Uani 1 1 d . . . C4 C 0.6610(11) -0.2053(5) 0.2824(5) 0.0328(13) Uani 1 1 d . . . H4 H 0.7573 -0.2144 0.2232 0.039 Uiso 1 1 calc R . . C5 C 0.5160(11) -0.2901(6) 0.3330(5) 0.0353(14) Uani 1 1 d . . . H5 H 0.5152 -0.3568 0.3079 0.042 Uiso 1 1 calc R . . C6 C 0.3732(11) -0.2803(6) 0.4183(5) 0.0335(13) Uani 1 1 d . . . C7 C 0.3738(13) -0.1809(6) 0.4526(5) 0.0435(16) Uani 1 1 d . . . H7 H 0.2731 -0.1708 0.5102 0.052 Uiso 1 1 calc R . . C8 C 0.5194(12) -0.0970(6) 0.4036(5) 0.0390(15) Uani 1 1 d . . . H8 H 0.5196 -0.0306 0.4290 0.047 Uiso 1 1 calc R . . C9 C 0.2055(13) -0.3718(6) 0.4719(5) 0.0451(16) Uani 1 1 d . . . H9A H 0.2788 -0.4555 0.4725 0.068 Uiso 1 1 calc R . . H9B H 0.0542 -0.3411 0.4286 0.068 Uiso 1 1 calc R . . H9C H 0.1767 -0.3771 0.5488 0.068 Uiso 1 1 calc R . . C10 C 0.9912(11) 0.2663(5) 0.2412(5) 0.0334(13) Uani 1 1 d . . . C11 C 0.8225(13) 0.3720(6) 0.1875(6) 0.0437(16) Uani 1 1 d . . . H11 H 0.6867 0.3671 0.1511 0.052 Uiso 1 1 calc R . . C12 C 0.8546(14) 0.4872(6) 0.1873(6) 0.0499(18) Uani 1 1 d . . . H12 H 0.7405 0.5619 0.1498 0.060 Uiso 1 1 calc R . . C13 C 1.0496(14) 0.4930(6) 0.2410(6) 0.0481(17) Uani 1 1 d . . . H13 H 1.0698 0.5718 0.2406 0.058 Uiso 1 1 calc R . . C14 C 1.2157(14) 0.3859(7) 0.2952(7) 0.055(2) Uani 1 1 d . . . H14 H 1.3500 0.3908 0.3327 0.066 Uiso 1 1 calc R . . C15 C 1.1886(13) 0.2705(7) 0.2957(7) 0.0504(18) Uani 1 1 d . . . H15 H 1.3036 0.1960 0.3327 0.060 Uiso 1 1 calc R . . C16 C 1.2673(12) 0.1420(6) 0.1030(5) 0.0385(14) Uani 1 1 d . . . H16A H 1.3359 0.0869 0.0633 0.058 Uiso 1 1 calc R . . H16B H 1.3928 0.1501 0.1473 0.058 Uiso 1 1 calc R . . H16C H 1.1945 0.2254 0.0488 0.058 Uiso 1 1 calc R . . Au1 Au 1.14059(4) -0.131925(19) 0.112985(16) 0.02990(10) Uani 1 1 d . . . Cl1 Cl 1.3036(3) -0.27260(14) 0.03206(12) 0.0362(3) Uani 1 1 d . . . N1 N 1.0866(9) 0.0878(5) 0.1770(4) 0.0322(11) Uani 1 1 d . . . N2 N 0.9635(9) 0.1473(4) 0.2405(4) 0.0327(11) Uani 1 1 d . . . N3 N 0.8006(9) 0.0859(5) 0.2958(4) 0.0335(11) 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 0.031(3) 0.028(3) 0.022(3) -0.002(2) -0.007(2) 0.000(2) C2 0.031(3) 0.022(3) 0.028(3) -0.007(2) -0.003(2) -0.001(2) C3 0.031(3) 0.027(3) 0.031(3) -0.011(2) -0.001(2) -0.001(2) C4 0.035(3) 0.033(3) 0.032(3) -0.014(3) 0.007(2) -0.004(3) C5 0.039(4) 0.026(3) 0.041(3) -0.015(3) -0.002(3) -0.003(3) C6 0.030(3) 0.027(3) 0.034(3) -0.002(2) -0.002(2) -0.001(2) C7 0.059(5) 0.044(4) 0.027(3) -0.013(3) 0.012(3) -0.010(3) C8 0.054(4) 0.031(3) 0.036(3) -0.017(3) 0.008(3) -0.008(3) C9 0.050(4) 0.038(4) 0.038(4) -0.004(3) 0.012(3) -0.011(3) C10 0.030(3) 0.028(3) 0.043(3) -0.015(3) 0.009(3) -0.008(2) C11 0.046(4) 0.038(3) 0.048(4) -0.022(3) -0.007(3) 0.005(3) C12 0.069(5) 0.028(3) 0.043(4) -0.011(3) 0.004(3) 0.007(3) C13 0.061(5) 0.031(3) 0.059(4) -0.020(3) 0.017(4) -0.018(3) C14 0.040(4) 0.047(4) 0.092(6) -0.039(4) 0.002(4) -0.012(3) C15 0.039(4) 0.035(3) 0.079(5) -0.026(4) -0.006(4) -0.001(3) C16 0.036(4) 0.037(3) 0.042(4) -0.015(3) 0.006(3) -0.009(3) Au1 0.02972(15) 0.02771(14) 0.03071(15) -0.01144(10) 0.00203(9) -0.00171(9) Cl1 0.0386(8) 0.0333(7) 0.0372(8) -0.0163(6) 0.0077(6) -0.0037(6) N1 0.030(3) 0.027(2) 0.039(3) -0.014(2) -0.002(2) 0.001(2) N2 0.030(3) 0.028(2) 0.043(3) -0.017(2) 0.004(2) -0.006(2) N3 0.033(3) 0.027(2) 0.043(3) -0.016(2) 0.000(2) -0.005(2) #=================================================================== # 10. 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 N1 1.341(8) . ? C1 C2 1.403(9) . ? C1 Au1 1.997(6) . ? C2 N3 1.349(7) . ? C2 C3 1.477(8) . ? C3 C4 1.388(8) . ? C3 C8 1.399(9) . ? C4 C5 1.383(9) . ? C4 H4 0.9500 . ? C5 C6 1.371(9) . ? C5 H5 0.9500 . ? C6 C7 1.391(9) . ? C6 C9 1.537(9) . ? C7 C8 1.375(10) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.367(9) . ? C10 C15 1.379(9) . ? C10 N2 1.436(7) . ? C11 C12 1.395(10) . ? C11 H11 0.9500 . ? C12 C13 1.369(11) . ? C12 H12 0.9500 . ? C13 C14 1.370(10) . ? C13 H13 0.9500 . ? C14 C15 1.388(10) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 N1 1.457(8) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? Au1 Cl1 2.2901(14) . ? N1 N2 1.354(7) . ? N2 N3 1.318(7) . ? 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 C1 C2 103.9(5) . . ? N1 C1 Au1 121.9(5) . . ? C2 C1 Au1 134.1(5) . . ? N3 C2 C1 110.5(5) . . ? N3 C2 C3 119.7(5) . . ? C1 C2 C3 129.8(5) . . ? C4 C3 C8 117.3(6) . . ? C4 C3 C2 122.8(5) . . ? C8 C3 C2 119.9(5) . . ? C5 C4 C3 120.7(5) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 121.6(6) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C7 118.3(6) . . ? C5 C6 C9 121.7(6) . . ? C7 C6 C9 119.9(6) . . ? C8 C7 C6 120.3(6) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C3 121.7(6) . . ? C7 C8 H8 119.2 . . ? C3 C8 H8 119.2 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 122.0(6) . . ? C11 C10 N2 119.2(6) . . ? C15 C10 N2 118.8(5) . . ? C10 C11 C12 118.4(6) . . ? C10 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? C13 C12 C11 120.3(6) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.4(6) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C15 120.2(7) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C10 C15 C14 118.6(7) . . ? C10 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C1 Au1 Cl1 177.13(15) . . ? C1 N1 N2 109.2(5) . . ? C1 N1 C16 129.9(5) . . ? N2 N1 C16 120.8(5) . . ? N3 N2 N1 110.7(4) . . ? N3 N2 C10 124.0(5) . . ? N1 N2 C10 125.1(5) . . ? N2 N3 C2 105.7(5) . . ? # End of Crystallographic Information File