Activation of C-F bonds in fluoroarenes by N-heterocyclic carbenes as an effective route to synthesize abnormal NHC complexes.
Kim, Youngsuk; Lee, Eunsung; Chemical communications (Cambridge, England) 52 (2016) 10922–10925; doi:10.1039/c6cc04896j

data_7124825
_publ_section_title
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 Activation of C-F bonds in fluoroarenes by N-heterocyclic carbenes as an
 effective route to synthesize abnormal NHC complexes.
;
_journal_issue                   72
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10922
_journal_page_last               10925
_journal_paper_doi               10.1039/c6cc04896j
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C41 H34 Au Cl F14 N2, C3.5 H8 O, 0.5(C)'
_chemical_formula_sum            'C45 H42 Au Cl F14 N2 O'
_chemical_formula_weight         1125.22
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-11 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.525(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0816(11)
_cell_length_b                   14.3924(11)
_cell_length_c                   20.4104(17)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.69
_cell_measurement_theta_min      2.27
_cell_volume                     4401.6(6)
_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_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1189
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            66030
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.754
_diffrn_reflns_theta_min         2.133
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.500
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0842 before and 0.0654 after correction.
The Ratio of minimum to maximum transmission is 0.9007.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_description       block
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.662
_refine_diff_density_min         -1.881
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         9353
_refine_ls_number_restraints     142
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+24.3746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0850
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6748
_reflns_number_total             9353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04896j2.cif
_cod_data_source_block           p21c_a
_cod_database_code               7124825
_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. Rigid bond restraints
 C43B, C43A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F12A, F12A, F12B, F13A, F13B, F13B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F5, F6A, F6B, F7A, F7B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C43B \\sim C43A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
F12A \\sim F12A \\sim F12B \\sim F13A \\sim F13B \\sim F13B: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
F5 \\sim F6A \\sim F6B \\sim F7A \\sim F7B: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(C43A) \\sim Ueq, Uanis(C43B) \\sim Ueq: with sigma of 0.03 and sigma for
terminal atoms of 0.02
Uanis(F12A) \\sim Ueq, Uanis(F12B) \\sim Ueq, Uanis(F13A) \\sim Ueq,
Uanis(F13B) \\sim Ueq, Uanis(F14A) \\sim Ueq, Uanis(F14B) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(F5) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F6B) \\sim Ueq, Uanis(F7A)
\\sim Ueq, Uanis(F7B) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Fixed Sof: F6A(0.5) F6B(0.5) F7A(0.5) F7B(0.5) F12A(0.5) F12B(0.5) F13A(0.3)
 F13B(0.7) F14A(0.6) F14B(0.4) C43B(0.5) C43A(0.5)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C10(H10), C20(H20), C23(H23)
5.b Secondary CH2 refined with riding coordinates:
 C42(H42A,H42B), C43B(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B)
5.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C16(H16), C19(H19), C21(H21)
5.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C),
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'