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_4132630
_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         'C26 H28 Au Cl N2 S, C H2 Cl2'
_chemical_formula_sum            'C27 H30 Au Cl3 N2 S'
_chemical_formula_weight         717.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.981(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.2745(12)
_cell_length_b                   7.7536(2)
_cell_length_c                   23.0815(7)
_cell_measurement_reflns_used    14333
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      72.7700
_cell_measurement_theta_min      4.1100
_cell_volume                     5428.3(3)
_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-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_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    -53.00  31.00   1.00    2.50    --  -36.69  57.00  30.00   84
  2  \w    -63.00  -3.00   1.00    2.50    --  -36.69  77.00-120.00   60
  3  \w    -38.00  31.00   1.00    2.50    --  -36.69  57.00-180.00   69
  4  \w    -88.00 -20.00   1.00    2.50    --  -36.69 123.00  53.00   68
  5  \w    -95.00  33.00   1.00    2.50    --  -36.69   0.00   0.00  128
  6  \w    -96.00 -69.00   1.00    2.50    --  -36.69 -57.00 150.00   27
  7  \w   -109.00 -75.00   1.00    2.50    --  -36.69-178.00 -60.00   34
  8  \w    -60.00 -35.00   1.00    2.50    --  -36.69-178.00 -60.00   25
  9  \w     80.00 107.00   1.00   10.00    --  111.00 -45.00 -90.00   27
 10  \w     97.00 129.00   1.00   10.00    --  111.00 -30.00 -90.00   32
 11  \w    100.00 126.00   1.00   10.00    --  111.00 -45.00-120.00   26
 12  \w    101.00 142.00   1.00   10.00    --  111.00 -86.00 -57.37   41
 13  \w     89.00 116.00   1.00   10.00    --  111.00 -61.00 -90.00   27
 14  \w     91.00 118.00   1.00   10.00    --  111.00 -45.00 -60.00   27
 15  \w     74.00 106.00   1.00   10.00    --  111.00-111.00-120.00   32
 16  \w     90.00 115.00   1.00   10.00    --  111.00-111.00-150.00   25
 17  \w     75.00 102.00   1.00   10.00    --  111.00 -94.00-120.00   27
 18  \w     91.00 116.00   1.00   10.00    --  111.00-111.00 -60.00   25
 19  \w     85.00 114.00   1.00   10.00    --  111.00-111.00   0.00   29
 20  \w    111.00 137.00   1.00   10.00    --  111.00 -77.00  60.00   26
 21  \w     89.00 128.00   1.00   10.00    --  111.00 -77.00 120.00   39
 22  \w     94.00 128.00   1.00   10.00    --  111.00 -45.00 120.00   34
 23  \w    119.00 146.00   1.00   10.00    --  111.00 -15.00 120.00   27
 24  \w    106.00 132.00   1.00   10.00    --  111.00 -30.00 150.00   26
 25  \w     97.00 128.00   1.00   10.00    --  111.00 -61.00 150.00   31
 26  \w     84.00 111.00   1.00   10.00    --  111.00 -45.00  60.00   27
 27  \w     72.00 105.00   1.00   10.00    --  111.00 -61.00   0.00   33
 28  \w     71.00 110.00   1.00   10.00    --  111.00 -98.00  15.00   39
 29  \w     78.00 105.00   1.00   10.00    --  111.00-111.00 150.00   27
 30  \w     61.00  96.00   1.00   10.00    --  111.00 -94.00 120.00   35
 31  \w     61.00  87.00   1.00   10.00    --  111.00-111.00 120.00   26
 32  \w     50.00  77.00   1.00   10.00    --  111.00 -77.00 120.00   27
 33  \w     52.00  87.00   1.00   10.00    --  111.00 -45.00 120.00   35
 34  \w     44.00  85.00   1.00   10.00    --  111.00 -77.00  60.00   41
 35  \w     50.00  90.00   1.00   10.00    --  111.00 -45.00  30.00   40
 36  \w     66.00  94.00   1.00   10.00    --  111.00 -94.00 -30.00   28
 37  \w     58.00 110.00   1.00   10.00    --  111.00-111.00 -90.00   52
 38  \w     69.00  94.00   1.00   10.00    --  111.00 -61.00-150.00   25
 39  \w     59.00  84.00   1.00   10.00    --  111.00 -61.00-120.00   25
 40  \w     47.00  74.00   1.00   10.00    --  111.00 -45.00 -90.00   27
 41  \w     46.00  79.00   1.00   10.00    --  111.00 -61.00 -90.00   33
 42  \w     47.00  74.00   1.00   10.00    --  111.00 -94.00-150.00   27
 43  \w     41.00  71.00   1.00   10.00    --  111.00-111.00-180.00   30
 44  \w     45.00  72.00   1.00   10.00    --  111.00 -61.00-180.00   27
 45  \w     46.00 106.00   1.00   10.00    --  111.00 -94.00 -90.00   60
 46  \w     44.00 100.00   1.00   10.00    --  111.00 -94.00  30.00   56
 47  \w     42.00  68.00   1.00   10.00    --  111.00-111.00 150.00   26
 48  \w     47.00  72.00   1.00   10.00    --  111.00 -61.00 150.00   25
 49  \w     41.00  82.00   1.00   10.00    --  111.00 -15.00 120.00   41
 50  \w     91.00 141.00   1.00   10.00    --  111.00  30.00 120.00   50
 51  \w    130.00 173.00   1.00   10.00    --  111.00  45.00 120.00   43
 52  \w    139.00 167.00   1.00   10.00    --  111.00  61.00  60.00   28
 53  \w    113.00 140.00   1.00   10.00    --  111.00  77.00 150.00   27
 54  \w    101.00 133.00   1.00   10.00    --  111.00 111.00 120.00   32
 55  \w    102.00 129.00   1.00   10.00    --  111.00  77.00  60.00   27
 56  \w    104.00 170.00   1.00   10.00    --  111.00  77.00  30.00   66
 57  \w    131.00 158.00   1.00   10.00    --  111.00  77.00 -90.00   27
 58  \w    113.00 140.00   1.00   10.00    --  111.00  61.00-150.00   27
 59  \w    142.00 172.00   1.00   10.00    --  111.00  15.00-150.00   30
 60  \w     96.00 125.00   1.00   10.00    --  111.00  45.00-120.00   29
 61  \w     92.00 136.00   1.00   10.00    --  111.00  30.00-150.00   44
 62  \w     94.00 171.00   1.00   10.00    --  111.00  61.00 -60.00   77
 63  \w     91.00 138.00   1.00   10.00    --  111.00  30.00  30.00   47
 64  \w     95.00 122.00   1.00   10.00    --  111.00  45.00 120.00   27
 65  \w     95.00 120.00   1.00   10.00    --  111.00  61.00  60.00   25
 66  \w     96.00 121.00   1.00   10.00    --  111.00  77.00 120.00   25
 67  \w     73.00 102.00   1.00   10.00    --  111.00  15.00   0.00   29
 68  \w     85.00 110.00   1.00   10.00    --  111.00  77.00 -90.00   25
 69  \w     94.00 119.00   1.00   10.00    --  111.00  61.00-180.00   25
 70  \w     40.00 147.00   1.00   10.00    --  111.00 -15.00 -60.00  107
 71  \w     62.00  87.00   1.00   10.00    --  111.00 -86.00 -57.37   25
 72  \w     41.00  73.00   1.00   10.00    --  111.00-111.00   0.00   32
 73  \w     42.00  87.00   1.00   10.00    --  111.00 -30.00 -90.00   45
 74  \w     44.00  78.00   1.00   10.00    --  111.00 -30.00 150.00   34
;
_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      -0.0362931000
_diffrn_orient_matrix_UB_12      0.1288840000
_diffrn_orient_matrix_UB_13      0.0003447000
_diffrn_orient_matrix_UB_21      0.0296385000
_diffrn_orient_matrix_UB_22      0.1510361000
_diffrn_orient_matrix_UB_23      -0.0049931000
_diffrn_orient_matrix_UB_31      -0.0196079000
_diffrn_orient_matrix_UB_32      -0.0098730000
_diffrn_orient_matrix_UB_33      -0.0707756000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36522
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.143
_diffrn_reflns_theta_min         4.076
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.762
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_correction_T_min  0.275
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_description       plate
_exptl_crystal_F_000             2816
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.015
_refine_diff_density_max         3.349
_refine_diff_density_min         -3.713
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5405
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0742P)^2^+101.4148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1522
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5001
_reflns_number_total             5405
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05184_si_004.cif
_cod_data_source_block           ed04179
_cod_original_cell_volume        5428.4(3)
_cod_database_code               4132630
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C27 H28 Au Cl3 N2 S'
_reflns_odcompleteness_completeness 98.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.59
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1A with sigma of 0.01 and sigma
for terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 C31, Cl32, Cl33, C41, Cl42, Cl43
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(Cl42)=Sof(Cl43)=1-FVAR(1)
 Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(Cl32)=Sof(Cl33)=FVAR(1)
5.a Free rotating group:
 C31(Cl32,Cl33), C41(Cl42,Cl43)
5.b Ternary CH refined with riding coordinates:
 C3(H3), C7(H7)
5.c Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C41(H41A,H41B)
5.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C17(H17), C18(H18), C20(H20), C21(H21),
 C23(H23), C24(H24), C26(H26), C27(H27)
5.e Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C29(H29A,
 H29B,H29C)
;
_shelx_res_checksum              14665
_shelx_hkl_checksum              42616
_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 1.523
_oxdiff_exptl_absorpt_empirical_full_min 0.727