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_7124824
_publ_section_title
;
 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 H35 F14 N2, F2 H'
_chemical_formula_sum            'C41 H36 F16 N2'
_chemical_formula_weight         860.72
_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   mixed
_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                 94.795(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7034(7)
_cell_length_b                   15.8896(10)
_cell_length_c                   29.1048(19)
_cell_measurement_reflns_used    9826
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.41
_cell_volume                     5854.3(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.997
_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       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            89209
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.727
_diffrn_reflns_theta_min         2.057
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0763 before and 0.0585 after correction. The Ratio of minimum to maximum transmission is 0.9296. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    0.977
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     589
_refine_ls_number_reflns         11136
_refine_ls_number_restraints     127
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0890
_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^)+(0.1570P)^2^+11.8608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2799
_refine_ls_wR_factor_ref         0.2909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8175
_reflns_number_total             11136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04896j2.cif
_cod_data_source_block           p21c_a
_cod_database_code               7124824
_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. Restrained distances
 F15-H15 \\sim F16-H15
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F12A \\sim F12B \\sim F13A \\sim F13B \\sim F14A \\sim F14B: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
F6 \\sim F5A \\sim F5B \\sim F7A \\sim F7B: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
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 0.007 and sigma for terminal atoms of 0.014
Uanis(F6) \\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F5B) \\sim Ueq, Uanis(F7A)
\\sim Ueq, Uanis(F7B) \\sim Ueq: with sigma of 0.007 and sigma for terminal
atoms of 0.014
4. Others
 Fixed Sof: F5A(0.85) F5B(0.15) F7A(0.85) F7B(0.15) F12A(0.7) F12B(0.3)
 F13A(0.7) F13B(0.3) F14A(0.7) F14B(0.3)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C8(H8), C18(H18), C21(H21)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C13(H13), C20(H20), C22(H22), C24(H24)
5.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), 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'