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_7124826
_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         'C34 H40 F3 N2, F2 H'
_chemical_formula_sum            'C34 H41 F5 N2'
_chemical_formula_weight         572.69
_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   mixed
_audit_creation_date             2016-06-01
_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                 101.779(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.227(7)
_cell_length_b                   17.040(6)
_cell_length_c                   20.143(8)
_cell_measurement_reflns_used    6679
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.39
_cell_volume                     6124(4)
_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
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_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  0.0985
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            38920
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.833
_diffrn_reflns_theta_min         2.066
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0987 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.8955.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.457
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         6502
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0734
_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^)+(0.0625P)^2^+17.8205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4235
_reflns_number_total             6502
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04896j2.cif
_cod_data_source_block           c2c_a
_cod_original_cell_volume        6125(4)
_cod_database_code               7124826
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All F(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F4-H4 \\sim F5-H4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F6 \\sim F7 \\sim F8: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F6) \\sim
Ueq, Uanis(F7) \\sim Ueq, Uanis(F8) \\sim Ueq: with sigma of 0.005 and sigma
for terminal atoms of 0.01
4. Others
 Fixed Sof: F1(0.7) F2(0.7) F3(0.7) F6(0.3) F7(0.3) F8(0.3)
5.a Ternary CH refined with riding coordinates:
 C13(H13), C15(H15), C26(H26), C28(H28)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C16(H16), C18(H18),
 C21(H21), C27(H27), C29(H29), C30(H30)
5.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,
 H34B,H34C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'