<i>meta</i>-C-H arylation of fluoroarenes <i>via</i> traceless directing group relay strategy.
Font, Marc; Spencer, Andrew R. A.; Larrosa, Igor; Chemical science 9 (2018) 7133–7137; doi:10.1039/c8sc02417k

data_1549725
_publ_section_title
;
 <i>meta</i>-C-H arylation of fluoroarenes <i>via</i> traceless directing
 group relay strategy.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              7133
_journal_page_last               7137
_journal_paper_doi               10.1039/c8sc02417k
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C15 H12 F2 O2'
_chemical_formula_sum            'C15 H12 F2 O2'
_chemical_formula_weight         262.25
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-10-23 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.892(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.442(2)
_cell_length_b                   13.4424(16)
_cell_length_c                   7.0546(10)
_cell_measurement_reflns_used    832
_cell_measurement_temperature    149.9(4)
_cell_measurement_theta_max      22.7750
_cell_measurement_theta_min      3.6810
_cell_volume                     1271.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      149.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -11.00  25.00   1.00   40.00    --  -18.77 -99.00-150.00   36
  2  \w    -18.00  40.00   1.00   40.00    --   20.18 -57.00 120.00   58
  3  \w    -52.00  76.00   1.00   40.00    --   20.18   0.00 150.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0012941000
_diffrn_orient_matrix_UB_12      0.0495829000
_diffrn_orient_matrix_UB_13      -0.0342145000
_diffrn_orient_matrix_UB_21      -0.0524048000
_diffrn_orient_matrix_UB_22      0.0035518000
_diffrn_orient_matrix_UB_23      0.0045047000
_diffrn_orient_matrix_UB_31      0.0067952000
_diffrn_orient_matrix_UB_32      0.0177307000
_diffrn_orient_matrix_UB_33      0.0947203000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.1117
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4604
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.343
_diffrn_reflns_theta_min         3.267
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0661
_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^)+(0.0487P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1633
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1256
_reflns_number_total             2332
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02417k2.cif
_cod_data_source_block           s4639a
_cod_depositor_comments
'Adding full bibliography for 1549724--1549725.cif.'
_cod_database_code               1549725
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00D(H00D), C00G(H00G)
2.b Idealised Me refined as rotating group:
 C00I(H00C,H00E,H00F), C00J(H00H,H00I,H00J)
;
_shelx_res_checksum              11011
_olex2_date_sample_data_collection 2017-03-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.658
_oxdiff_exptl_absorpt_empirical_full_min 0.466