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_4132629
_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         'C22 H34 Au Cl P2 S2, 2(C4 H8 O)'
_chemical_formula_sum            'C30 H50 Au Cl O2 P2 S2'
_chemical_formula_weight         801.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.6290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.3899(2)
_cell_length_b                   17.95980(10)
_cell_length_c                   18.6379(2)
_cell_measurement_reflns_used    49852
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      73.0010
_cell_measurement_theta_min      3.5740
_cell_volume                     6966.94(12)
_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)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_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    -34.00  28.00   1.00    1.00    --  -36.84  37.00-150.00   62
  2  \w    -96.00 -43.00   1.00    1.00    --  -36.84 178.00  60.00   53
  3  \w   -100.00 -37.00   1.00    1.00    --  -36.84 143.00  -9.00   63
  4  \w    -91.00 -23.00   1.00    1.00    --  -36.84 127.00-179.00   68
  5  \w   -107.00 -59.00   1.00    1.00    --  -36.84 178.00-120.00   48
  6  \w   -106.00  31.00   1.00    1.00    --  -36.84   0.00-180.00  137
  7  \w    -88.00 -37.00   1.00    1.00    --  -36.84-178.00 -90.00   51
  8  \w   -101.00 -61.00   1.00    1.00    --  -36.84-178.00-180.00   40
  9  \w    -82.00 -24.00   1.00    1.00    --  -36.84 -77.00 120.00   58
 10  \w     62.00  91.00   1.00    4.00    --  111.00 -47.00 140.87   29
 11  \w    107.00 132.00   1.00    4.00    --  111.00 -30.00  90.00   25
 12  \w    122.00 161.00   1.00    4.00    --  111.00  15.00 150.00   39
 13  \w    145.00 176.00   1.00    4.00    --  111.00  45.00  60.00   31
 14  \w    146.00 176.00   1.00    4.00    --  111.00  15.00  30.00   30
 15  \w    148.00 173.00   1.00    4.00    --  111.00  61.00   0.00   25
 16  \w    149.00 176.00   1.00    4.00    --  111.00  15.00 -90.00   27
 17  \w    118.00 173.00   1.00    4.00    --  111.00  61.00-180.00   55
 18  \w    115.00 142.00   1.00    4.00    --  111.00  45.00-120.00   27
 19  \w    115.00 143.00   1.00    4.00    --  111.00  77.00-120.00   28
 20  \w    111.00 144.00   1.00    4.00    --  111.00 111.00-120.00   33
 21  \w    111.00 176.00   1.00    4.00    --  111.00  61.00 -90.00   65
 22  \w    122.00 155.00   1.00    4.00    --  111.00 111.00 -30.00   33
 23  \w    110.00 137.00   1.00    4.00    --  111.00 178.00 -90.00   27
 24  \w    101.00 161.00   1.00    4.00    --  111.00 111.00  30.00   60
 25  \w    110.00 137.00   1.00    4.00    --  111.00  45.00 150.00   27
 26  \w     95.00 141.00   1.00    4.00    --  111.00  45.00  60.00   46
 27  \w    103.00 130.00   1.00    4.00    --  111.00  30.00   0.00   27
 28  \w     95.00 175.00   1.00    4.00    --  111.00  45.00 -60.00   80
 29  \w    111.00 136.00   1.00    4.00    --  111.00 -25.00-106.61   25
 30  \w     97.00 128.00   1.00    4.00    --  111.00 -45.00-180.00   31
 31  \w     87.00 127.00   1.00    4.00    --  111.00 -61.00-180.00   40
 32  \w     87.00 116.00   1.00    4.00    --  111.00-111.00-180.00   29
 33  \w     84.00 109.00   1.00    4.00    --  111.00 -94.00-150.00   25
 34  \w     84.00 111.00   1.00    4.00    --  111.00-111.00 -90.00   27
 35  \w     87.00 116.00   1.00    4.00    --  111.00-111.00 -60.00   29
 36  \w     93.00 125.00   1.00    4.00    --  111.00 -61.00 -30.00   32
 37  \w     93.00 134.00   1.00    4.00    --  111.00 -15.00 -90.00   41
 38  \w     91.00 123.00   1.00    4.00    --  111.00 -61.00   0.00   32
 39  \w    109.00 135.00   1.00    4.00    --  111.00 -77.00  30.00   26
 40  \w     89.00 123.00   1.00    4.00    --  111.00-127.00 104.00   34
 41  \w     91.00 116.00   1.00    4.00    --  111.00-111.00  60.00   25
 42  \w     87.00 128.00   1.00    4.00    --  111.00 -61.00  60.00   41
 43  \w     95.00 122.00   1.00    4.00    --  111.00 -15.00 120.00   27
 44  \w     73.00 100.00   1.00    4.00    --  111.00  15.00 150.00   27
 45  \w     73.00 110.00   1.00    4.00    --  111.00 -45.00  60.00   37
 46  \w     82.00 122.00   1.00    4.00    --  111.00 -36.00  22.99   40
 47  \w     70.00  97.00   1.00    4.00    --  111.00 -45.00  30.00   27
 48  \w     67.00 104.00   1.00    4.00    --  111.00 -81.00 -30.59   37
 49  \w     67.00  94.00   1.00    4.00    --  111.00 -94.00   0.00   27
 50  \w     67.00 116.00   1.00    4.00    --  111.00-111.00 -30.00   49
 51  \w     68.00 108.00   1.00    4.00    --  111.00 -45.00-120.00   40
 52  \w     77.00 102.00   1.00    4.00    --  111.00  15.00 -90.00   25
 53  \w     85.00 112.00   1.00    4.00    --  111.00  77.00-120.00   27
 54  \w     97.00 122.00   1.00    4.00    --  111.00  30.00-180.00   25
 55  \w     64.00  91.00   1.00    4.00    --  111.00 -61.00 -60.00   27
 56  \w     53.00  93.00   1.00    4.00    --  111.00 -25.00-106.61   40
 57  \w     46.00  71.00   1.00    4.00    --  111.00 -61.00 -30.00   25
 58  \w     42.00  68.00   1.00    4.00    --  111.00 -36.00  22.99   26
 59  \w     45.00  85.00   1.00    4.00    --  111.00 -61.00  60.00   40
 60  \w     68.00 101.00   1.00    4.00    --  111.00 -94.00  90.00   33
 61  \w     85.00 116.00   1.00    4.00    --  111.00-111.00 150.00   31
 62  \w     53.00  80.00   1.00    4.00    --  111.00 -77.00  30.00   27
 63  \w     48.00 104.00   1.00    4.00    --  111.00-111.00   0.00   56
 64  \w     42.00  67.00   1.00    4.00    --  111.00-111.00  60.00   25
 65  \w     44.00  71.00   1.00    4.00    --  111.00-111.00  30.00   27
 66  \w     42.00 109.00   1.00    4.00    --  111.00 -94.00  30.00   67
 67  \w     49.00  75.00   1.00    4.00    --  111.00 -15.00 120.00   26
 68  \w     45.00  70.00   1.00    4.00    --  111.00 -30.00  90.00   25
 69  \w     42.00 118.00   1.00    4.00    --  111.00 -30.00 120.00   76
 70  \w     74.00 135.00   1.00    4.00    --  111.00  15.00  30.00   61
 71  \w    103.00 130.00   1.00    4.00    --  111.00  61.00   0.00   27
 72  \w     71.00  98.00   1.00    4.00    --  111.00 178.00 -90.00   27
 73  \w     66.00  91.00   1.00    4.00    --  111.00 178.00 150.00   25
 74  \w     44.00  92.00   1.00    4.00    --  111.00 -30.00  30.00   48
 75  \w     46.00  89.00   1.00    4.00    --  111.00 -94.00  60.00   43
 76  \w     43.00  71.00   1.00    4.00    --  111.00-111.00 150.00   28
 77  \w     44.00 118.00   1.00    4.00    --  111.00 -45.00 -90.00   74
 78  \w     66.00 117.00   1.00    4.00    --  111.00 -83.00-151.46   51
 79  \w     50.00 133.00   1.00    4.00    --  111.00 -77.00-180.00   83
 80  \w     51.00 100.00   1.00    4.00    --  111.00-111.00-150.00   49
 81  \w     44.00  76.00   1.00    4.00    --  111.00 -94.00-120.00   32
;
_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      0.0584729000
_diffrn_orient_matrix_UB_12      -0.0105009000
_diffrn_orient_matrix_UB_13      0.0755231000
_diffrn_orient_matrix_UB_21      -0.0451552000
_diffrn_orient_matrix_UB_22      -0.0205429000
_diffrn_orient_matrix_UB_23      0.0424141000
_diffrn_orient_matrix_UB_31      0.0038562000
_diffrn_orient_matrix_UB_32      -0.0826452000
_diffrn_orient_matrix_UB_33      -0.0201315000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            94068
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.923
_diffrn_reflns_theta_min         3.545
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.814
_exptl_absorpt_correction_T_max  0.452
_exptl_absorpt_correction_T_min  0.183
_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    1.528
_exptl_crystal_description       block
_exptl_crystal_F_000             3232
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.092
_refine_diff_density_max         2.793
_refine_diff_density_min         -1.226
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     743
_refine_ls_number_reflns         13776
_refine_ls_number_restraints     156
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0436P)^2^+20.4385P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12528
_reflns_number_total             13776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05184_si_007.cif
_cod_data_source_block           ed04113
_cod_original_cell_volume        6966.94(11)
_cod_database_code               4132629
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'Au P2 S2 Cl O2 C30 H49'
_reflns_odcompleteness_completeness 97.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.83
_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
 O301, C301, C302, C303, C304, O311, C311, C312, C313, C314
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{O301, C301, C302, C303, C304} sigma for 1-2: 0.02, 1-3: 0.04
{O311, C311, C312, C313, C314} sigma for 1-2: 0.02, 1-3: 0.04
{O301, C304, C303, C302, C301} sigma for 1-2: 0.02, 1-3: 0.04
{O311, C314, C313, C312, C311} sigma for 1-2: 0.02, 1-3: 0.04
as
{O101, C101, C102, C103, C104}
5. Others
 Sof(O311)=Sof(C311)=Sof(H31A)=Sof(H31B)=Sof(C312)=Sof(H31C)=Sof(H31D)=
 Sof(C313)=Sof(H31E)=Sof(H31F)=Sof(C314)=Sof(H31G)=Sof(H31H)=1-FVAR(1)
 Sof(O301)=Sof(C301)=Sof(H30A)=Sof(H30B)=Sof(C302)=Sof(H30C)=Sof(H30D)=
 Sof(C303)=Sof(H30E)=Sof(H30F)=Sof(C304)=Sof(H30G)=Sof(H30H)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C12(H12A,H12B), C14(H14A,H14B), C23(H23A,H23B),
 C25(H25A,H25B), C34(H34A,H34B), C36(H36A,H36B), C301(H30A,H30B), C302(H30C,
 H30D), C303(H30E,H30F), C304(H30G,H30H), C311(H31A,H31B), C312(H31C,H31D),
 C313(H31E,H31F), C314(H31G,H31H), C401(H40E,H40F), C402(H40A,H40B), C403(H40C,
 H40D), C404(H40H,H40G), C201(H20A,H20B), C202(H20G,H20H), C203(H20E,H20F),
 C204(H20C,H20D), C101(H10C,H10D), C102(H10A,H10B), C103(H10E,H10F), C104(H10G,
 H10H)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C17(H17), C18(H18), C20(H20), C21(H21),
 C28(H28), C29(H29), C31(H31), C32(H32), C39(H39), C40(H40), C42(H42), C43(H43)
6.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C),
 C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C26(H26C,H26A,
 H26B), C33(H33A,H33B,H33C), C35(H35C,H35A,H35B), C37(H37B,H37A,H37C), C44(H44A,
 H44B,H44C)
;
_shelx_res_checksum              26656
_shelx_hkl_checksum              98356
_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 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.622