Visible-light-driven difluoroacetamidation of unactive arenes and heteroarenes by direct C-H functionalization at room temperature.
Wang, Lin; Wei, Xiao-Jing; Jia, Wen-Liang; Zhong, Jian-Ji; Wu, Li-Zhu; Liu, Qiang; Organic letters 16 (2014) 5842–5845; doi:10.1021/ol502676y

data_1518196
_publ_section_title
;
 Visible-light-driven difluoroacetamidation of unactive arenes and
 heteroarenes by direct C-H functionalization at room temperature.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5842
_journal_page_last               5845
_journal_paper_doi               10.1021/ol502676y
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C15 H17 F2 N O5'
_chemical_formula_sum            'C15 H17 F2 N O5'
_chemical_formula_weight         329.29
_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     direct
_audit_creation_date             2014-07-11
_audit_creation_method
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Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
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_cell_angle_alpha                90
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_cell_formula_units_Z            4
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_cell_measurement_reflns_used    3291
_cell_measurement_temperature    292.82(10)
_cell_measurement_theta_max      70.7020
_cell_measurement_theta_min      4.6080
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.82(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega  -80.00  -54.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -120.0000 17

  2 omega   33.00   60.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 18

  3 omega  -16.00   29.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 30

  4 omega  -79.00  -53.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 17

  5 omega    4.00   29.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   50.0000   60.0000 17

  6 omega  -55.00  -29.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   50.0000   60.0000 17

  7 omega  -15.00   64.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000    0.0000 53

  8 omega   31.00   68.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  -30.0000 25

  9 omega   32.00  116.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   38.0000  -90.0000 56

 10 omega   74.00  110.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  -30.0000 24

 11 omega   28.00  128.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  120.0000 67

 12 omega   89.00  168.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000  120.0000 53

 13 omega   45.00   94.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -180.0000 33

 14 omega   39.00   93.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000    0.0000 36

 15 omega   66.00   93.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000    0.0000 18

 16 omega   60.00  102.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  120.0000 28

 17 omega   48.00   76.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -180.0000 19

 18 omega  147.00  178.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  150.0000 21

 19 omega   42.00   81.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -60.0000 26

 20 omega   52.00   91.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -60.0000 26

 21 omega   88.00  113.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000  106.0000 17

 22 omega   55.00  175.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000 -120.0000 80
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1245495000
_diffrn_orient_matrix_UB_12      -0.0979847000
_diffrn_orient_matrix_UB_13      -0.0127670000
_diffrn_orient_matrix_UB_21      0.0491434000
_diffrn_orient_matrix_UB_22      -0.0818771000
_diffrn_orient_matrix_UB_23      0.0808600000
_diffrn_orient_matrix_UB_31      -0.0689994000
_diffrn_orient_matrix_UB_32      0.1184235000
_diffrn_orient_matrix_UB_33      0.0453448000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5408
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.603
_diffrn_reflns_theta_min         4.324
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.054(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0775P)^2^+0.3377P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2561
_reflns_number_total             2824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502676y_si_002.cif
_cod_data_source_block           wangling0710
_cod_depositor_comments          'Adding full bibliography for 1518196.cif.'
_cod_original_cell_volume        1512.15(10)
_cod_database_code               1518196
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.14
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_reflns_odcompleteness_theta     66.97
_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.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C15(H15)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              93583
_shelx_hkl_checksum              29881
_olex2_submission_special_instructions 'No special instructions were received'