In Situ Formation of N-Heterocyclic Carbene-Bound Single-Molecule Junctions.
Doud, Evan A.; Inkpen, Michael S.; Lovat, Giacomo; Montes, Enrique; Paley, Daniel W.; Steigerwald, Michael L.; Vázquez, Héctor; Venkataraman, Latha; Roy, Xavier; Journal of the American Chemical Society 140 (2018) 8944–8949; doi:10.1021/jacs.8b05184

data_4132628
_publ_section_title
;
 In Situ Formation of N-Heterocyclic Carbene-Bound Single-Molecule
 Junctions.
;
_journal_issue                   28
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8944
_journal_page_last               8949
_journal_paper_doi               10.1021/jacs.8b05184
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C20 H24 Au Cl N2 S'
_chemical_formula_sum            'C20 H24 Au Cl N2 S'
_chemical_formula_weight         556.89
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                104.024(3)
_cell_angle_beta                 106.985(3)
_cell_angle_gamma                94.210(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5453(3)
_cell_length_b                   10.0951(3)
_cell_length_c                   12.3151(4)
_cell_measurement_reflns_used    7046
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      72.8450
_cell_measurement_theta_min      3.8870
_cell_volume                     973.77(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -14.00  31.00   1.00    1.00    --  -36.44  77.00  60.00   45
  2  \w    -45.00 -19.00   1.00    1.00    --  -36.44  77.00  60.00   26
  3  \w    -67.00 -37.00   1.00    1.00    --  -36.44 178.00 -90.00   30
  4  \w   -107.00 -20.00   1.00    1.00    --  -36.44 -19.00 150.00   87
  5  \w      4.00  71.00   1.00    1.00    --   36.44 -99.00  60.00   67
  6  \w     44.00 129.00   1.00    1.00    --  111.00 -61.00  90.00   85
  7  \w     83.00 108.00   1.00    1.00    --  111.00 -94.00  30.00   25
  8  \w     80.00 114.00   1.00    1.00    --  111.00-111.00  90.00   34
  9  \w     87.00 112.00   1.00    1.00    --  111.00 -77.00  90.00   25
 10  \w     83.00 115.00   1.00    1.00    --  111.00-111.00 150.00   32
 11  \w     44.00  72.00   1.00    1.00    --  111.00 -77.00  90.00   28
 12  \w     42.00  83.00   1.00    1.00    --  111.00 -94.00  60.00   41
 13  \w     47.00 111.00   1.00    1.00    --  111.00-111.00   0.00   64
 14  \w     76.00 102.00   1.00    1.00    --  111.00-111.00 -60.00   26
 15  \w     74.00 113.00   1.00    1.00    --  111.00-111.00 -30.00   39
 16  \w     77.00 109.00   1.00    1.00    --  111.00-111.00-120.00   32
 17  \w     58.00 116.00   1.00    1.00    --  111.00 -30.00   0.00   58
 18  \w     95.00 169.00   1.00    1.00    --  111.00  45.00 -60.00   74
 19  \w    153.00 178.00   1.00    1.00    --  111.00  77.00 -30.00   25
 20  \w    132.00 177.00   1.00    1.00    --  111.00 111.00   0.00   45
 21  \w    138.00 175.00   1.00    1.00    --  111.00  77.00  90.00   37
 22  \w    138.00 176.00   1.00    1.00    --  111.00  77.00 120.00   38
 23  \w    120.00 145.00   1.00    1.00    --  111.00 178.00 150.00   25
 24  \w    111.00 137.00   1.00    1.00    --  111.00 178.00 120.00   26
 25  \w    109.00 148.00   1.00    1.00    --  111.00 178.00  30.00   39
 26  \w    103.00 135.00   1.00    1.00    --  111.00 111.00  60.00   32
 27  \w     99.00 127.00   1.00    1.00    --  111.00  77.00 -30.00   28
 28  \w     98.00 174.00   1.00    1.00    --  111.00  45.00 -30.00   76
 29  \w    109.00 177.00   1.00    1.00    --  111.00  15.00-120.00   68
 30  \w    113.00 177.00   1.00    1.00    --  111.00  30.00-180.00   64
 31  \w     98.00 143.00   1.00    1.00    --  111.00  77.00  60.00   45
 32  \w     87.00 112.00   1.00    1.00    --  111.00  77.00 120.00   25
 33  \w     57.00 102.00   1.00    1.00    --  111.00 178.00 150.00   45
 34  \w     44.00  78.00   1.00    1.00    --  111.00 -45.00 -30.00   34
 35  \w     51.00  78.00   1.00    1.00    --  111.00 -94.00 -90.00   27
 36  \w     44.00  79.00   1.00    1.00    --  111.00-111.00-180.00   35
 37  \w     44.00 125.00   1.00    1.00    --  111.00 -45.00-180.00   81
 38  \w     23.00  72.00   1.00    1.00    --   36.44 -99.00-120.00   49
 39  \w   -102.00 -13.00   1.00    1.00    --  -36.44 -77.00 -60.00   89
 40  \w   -107.00 -36.00   1.00    1.00    --  -36.44-178.00  30.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1078404000
_diffrn_orient_matrix_UB_12      0.0923637000
_diffrn_orient_matrix_UB_13      -0.0626508000
_diffrn_orient_matrix_UB_21      0.1527081000
_diffrn_orient_matrix_UB_22      0.0685663000
_diffrn_orient_matrix_UB_23      -0.0196360000
_diffrn_orient_matrix_UB_31      -0.0382544000
_diffrn_orient_matrix_UB_32      -0.1100961000
_diffrn_orient_matrix_UB_33      -0.1192265000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8851
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.947
_diffrn_reflns_theta_min         3.905
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    16.486
_exptl_absorpt_correction_T_max  0.638
_exptl_absorpt_correction_T_min  0.100
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_description       prism
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.933
_refine_diff_density_min         -1.090
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       0.00090(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+1.3088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0616
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3852
_reflns_number_total             3877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05184_si_003.cif
_cod_data_source_block           ed04101_2_corr
_cod_database_code               4132628
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'H24 C20 N2 S1 Cl1 Au1'
_shelx_estimated_absorpt_t_max   0.309
_shelx_estimated_absorpt_t_min   0.064
_reflns_odcompleteness_completeness 98.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.83
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C3(H3), C19(H19), C4(H4), C16(H16), C15(H15), C6(H6)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C20(H20A,H20B,
 H20C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              69318
_shelx_hkl_checksum              72119
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.296
_oxdiff_exptl_absorpt_empirical_full_min 0.738