C-F bond activation of perfluorinated arenes by a bioxazoline-derived N-heterocyclic carbene.
Emerson-King, Jack; Hauser, Simone A.; Chaplin, Adrian B.; Organic & biomolecular chemistry 15 (2017) 787–789; doi:10.1039/c6ob02556k

data_7155423
_publ_section_title
;
 C-F bond activation of perfluorinated arenes by a bioxazoline-derived
 N-heterocyclic carbene.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              787
_journal_page_last               789
_journal_paper_doi               10.1039/c6ob02556k
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C18 H16 F8 N2 O2, C7 F8'
_chemical_formula_sum            'C25 H16 F16 N2 O2'
_chemical_formula_weight         680.40
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-15
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
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_audit_update_record
;
2016-11-18 deposited with the CCDC.
2016-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.3482(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4101(2)
_cell_length_b                   11.66149(18)
_cell_length_c                   15.7982(2)
_cell_measurement_reflns_used    16428
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.2720
_cell_measurement_theta_min      3.1880
_cell_volume                     2560.10(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -25.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215  -99.0000 -120.0000 90

  2 omega   -3.00   99.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215   38.0000   30.0000 102

  3 omega  -10.00  102.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215   77.0000  150.0000 112

  4 omega  -98.00    5.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153  -57.0000  -60.0000 103

  5 omega  -25.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215  -99.0000   60.0000 90

  6 omega   35.00  113.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215  178.0000   30.0000 78

  7 omega   -3.00   99.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215   38.0000  -60.0000 102

  8 omega -100.00    2.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153  -38.0000   30.0000 102

  9 omega -114.00  -57.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153 -178.0000   30.0000 57

 10 omega   35.00  113.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215  178.0000 -150.0000 78

 11 omega -103.00  -69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153  -77.0000 -150.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction: Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0329890000
_diffrn_orient_matrix_UB_12      0.0242961000
_diffrn_orient_matrix_UB_13      0.0212303000
_diffrn_orient_matrix_UB_21      -0.0134196000
_diffrn_orient_matrix_UB_22      -0.0557429000
_diffrn_orient_matrix_UB_23      0.0102915000
_diffrn_orient_matrix_UB_31      0.0365688000
_diffrn_orient_matrix_UB_32      0.0014472000
_diffrn_orient_matrix_UB_33      0.0401356000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            50461
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.372
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.932
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_recrystallization_method
'Crystals grown from C6F5CF3/heptane at 293 K'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.628
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_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         5225
_refine_ls_number_restraints     190
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0840P)^2^+1.2142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1414
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4202
_reflns_number_total             5225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02556k3.cif
_cod_data_source_block           0145abc15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155423.cif.
;
_cod_original_cell_volume        2560.09(7)
_cod_database_code               7155423
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C15A, C13}
{C15, C13A}
3. Restrained distances
 F28A-C23 \\sim F30-C23 \\sim F29-C23 \\sim F29A-C23 \\sim F28-C23 \\sim
F30A-C23
 with sigma of 0.01
 F28-F29 \\sim F29-F30 \\sim F30-F28 \\sim F28A-F29A \\sim F29A-F30A \\sim
F30A-F28A
 with sigma of 0.01
 C20-F28 \\sim C20-F29 \\sim C20-F30 \\sim C20-F28A \\sim C20-F29A \\sim
C20-F30A
 with sigma of 0.01
 F14-C13 \\sim F14A-C13A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
F14 \\sim F14A \\sim F28 \\sim F28A \\sim F29 \\sim F29A \\sim F30 \\sim F30A
\\sim C13 \\sim C13A \\sim C15 \\sim C15A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C13) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C15A)
\\sim Ueq, Uanis(F14) \\sim Ueq, Uanis(F14A) \\sim Ueq, Uanis(F30) \\sim Ueq,
Uanis(F29) \\sim Ueq, Uanis(F28A) \\sim Ueq, Uanis(F30A) \\sim Ueq, Uanis(F28)
\\sim Ueq, Uanis(F29A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C15A) = Uanis(C13)
Uanis(C15) = Uanis(C13A)
5. Others
 Sof(F28A)=Sof(F29A)=Sof(F30A)=1-FVAR(1)
 Sof(F28)=Sof(F29)=Sof(F30)=FVAR(1)
 Fixed Sof: F14(0.5) F14A(0.5) C13(0.5) H13A(0.5) H13B(0.5) C13A(0.5)
 H13C(0.5) H13D(0.5) C15(0.5) H15A(0.5) H15B(0.5) H15C(0.5) C15A(0.5) H15D(0.5)
 H15E(0.5) H15F(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B), C13A(H13C,H13D)
6.b Me refined with riding coordinates:
 C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F)
6.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'