Stable N-heterocyclic carbene (NHC) cyclometalated (C^C) gold(iii) complexes as blue‒blue green phosphorescence emitters
von Arx, Tobias; Szentkuti, Alexander; Zehnder, Thomas N.; Blacque, Olivier; Venkatesan, Koushik; Journal of Materials Chemistry C 5 (2017) 3765–; doi:10.1039/C6TC05551F

data_7236468
_publ_section_title
;
 Stable N-heterocyclic carbene (NHC) cyclometalated (C^C) gold(iii)
 complexes as blue--blue green phosphorescence emitters
;
_journal_issue                   15
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3765
_journal_paper_doi               10.1039/C6TC05551F
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         'C26 H17 Au F2 N2, 0.5(C6 H14)'
_chemical_formula_sum            'C29 H24 Au F2 N2'
_chemical_formula_weight         635.47
_chemical_name_systematic
'(1-methyl-3-phenyl-2,3-dihydro-1H-imidazole)-bis(4-fluorophenylethynyl)-gold(iii) hexane solvate 2:1'
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-08-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-12-14 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.884(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.6163(2)
_cell_length_b                   6.87229(10)
_cell_length_c                   15.3236(3)
_cell_measurement_reflns_used    14320
_cell_measurement_temperature    183(1)
_cell_measurement_theta_max      76.5
_cell_measurement_theta_min      3.1
_cell_volume                     1232.86(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      183(1)
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -44.00   26.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615   37.0000  -30.0000 70

  2 omega  -89.00  -42.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615  125.0000   60.0000 47

  3 omega -112.00  -11.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615  -57.0000  -60.0000 101

  4 omega   -6.00   35.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615   37.0000   90.0000 41

  5 omega  -30.00   -3.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615  125.0000   60.0000 27

  6 omega  -47.00  -19.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615   37.0000   90.0000 28

  7 omega   34.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615   57.0000  150.0000 81

  8 omega   36.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615  -99.0000  -60.0000 47

  9 omega  138.00  177.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 39

 10 omega   36.00   90.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 54

 11 omega   83.00  109.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 26

 12 omega   36.00   76.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   90.0000 40

 13 omega   83.00  177.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 94

 14 omega   78.00  109.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -30.0000 31

 15 omega  142.00  176.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000  120.0000 34

 16 omega   65.00  103.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   90.0000 38

 17 omega   53.00   80.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 27

 18 omega   51.00   78.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 27

 19 omega   83.00  109.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -90.0000 26

 20 omega   86.00  116.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   60.0000 30

 21 omega  130.00  156.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 26

 22 omega   83.00  160.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 77

 23 omega  119.00  170.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 51

 24 omega   38.00   64.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  150.0000 26

 25 omega   68.00  113.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  150.0000 45

 26 omega   87.00  136.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 49

 27 omega   99.00  144.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   34.0000  -36.0000 45

 28 omega   29.00   82.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   60.0000 53

 29 omega   64.00   90.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 26

 30 omega   90.00  162.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 72

 31 omega   85.00  174.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 89

 32 omega   43.00   88.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 45

 33 omega  117.00  169.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -180.0000 52

 34 omega   48.00   78.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 30

 35 omega   49.00   97.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -150.0000 48

 36 omega   58.00   89.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -180.0000 31

 37 omega   94.00  121.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 27

 38 omega  143.00  176.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 33

 39 omega   43.00   68.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   30.0000 25

 40 omega   96.00  122.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   30.0000 26

 41 omega   30.00   67.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -180.0000 37

 42 omega   44.00   70.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -90.0000 26

 43 omega   56.00   82.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   90.0000 26

 44 omega   86.00  167.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -150.0000 81

 45 omega -115.00  -11.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615  -57.0000 -120.0000 104

 46 omega  -49.00   35.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615   37.0000 -120.0000 84

 47 omega  -96.00   -2.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615  125.0000  -30.0000 94

 48 omega -119.00   -7.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615  -77.0000 -150.0000 112

 49 omega  -49.00   35.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615   37.0000 -180.0000 84

 50 omega    7.00  119.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615   77.0000  150.0000 112

 51 omega    4.00   33.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615   88.0000  112.9352 29

 52 omega   23.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615 -125.0000  -60.0000 75

 53 omega   11.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615   57.0000   60.0000 104

 54 omega   83.00  165.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 82

 55 omega   83.00  178.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 95

 56 omega   29.00  109.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -120.0000 80

 57 omega   35.00   91.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 56
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1275634000
_diffrn_orient_matrix_UB_12      0.0349243000
_diffrn_orient_matrix_UB_13      0.0201527000
_diffrn_orient_matrix_UB_21      -0.0072012000
_diffrn_orient_matrix_UB_22      0.1994299000
_diffrn_orient_matrix_UB_23      0.0434039000
_diffrn_orient_matrix_UB_31      0.0313844000
_diffrn_orient_matrix_UB_32      -0.0962452000
_diffrn_orient_matrix_UB_33      0.0972070000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21225
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.734
_diffrn_reflns_theta_min         3.108
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.496
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.380
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_description       needle
_exptl_crystal_F_000             618
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.847
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2807
_refine_ls_number_restraints     111
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+1.8337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0647
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2717
_reflns_number_total             2807
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6tc05551f2.cif
_cod_data_source_block           1b_CCDC-1497780
_cod_database_code               7236468
_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. Restrained distances
 C11-C12
 1.17 with sigma of 0.005
 Au1-C11 \\sim Au1-C17
 with sigma of 0.005
 C12-C13 \\sim C18-C19
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim F2: within 3A with
sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H10C(0.5) C17(0.5) C18(0.5) C19(0.5) C20(0.5)
 H20(0.5) C21(0.5) H21(0.5) C22(0.5) C23(0.5) H23(0.5) C24(0.5) H24(0.5)
 F2(0.5) C25(0.5) H25A(0.5) H25B(0.5) C26(0.5) H26A(0.5) H26B(0.5) C27(0.5)
 H27A(0.5) H27B(0.5) H27C(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C14(H14), C15(H15), C20(H20),
 C21(H21), C23(H23), C24(H24)
5.c Fitted hexagon refined as free rotating group:
 C19(C20,C21,C22,C23,C24)
5.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              10963
_shelx_hkl_checksum              17134
_shelx_shelxl_version_number     2014/7