CuSO4-Mediated Decarboxylative Difluoroacetamidation of α,β-Unsaturated Carboxylic Acids.
Chen, Qiao; Wang, Chao; Zhou, Jiawei; Wang, Yanan; Xu, Zhaoqing; Wang, Rui; The Journal of organic chemistry 81 (2016) 2639–2645; doi:10.1021/acs.joc.6b00031

data_4036613
_publ_section_title
;
 CuSO4-Mediated Decarboxylative Difluoroacetamidation of \a,\b-Unsaturated
 Carboxylic Acids.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2639
_journal_page_last               2645
_journal_paper_doi               10.1021/acs.joc.6b00031
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C16 H19 F2 N O'
_chemical_formula_sum            'C16 H19 F2 N O'
_chemical_formula_weight         279.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                73.54(3)
_cell_angle_beta                 85.59(3)
_cell_angle_gamma                81.51(3)
_cell_formula_units_Z            2
_cell_length_a                   5.7679(19)
_cell_length_b                   9.859(3)
_cell_length_c                   13.531(4)
_cell_measurement_reflns_used    760
_cell_measurement_temperature    295.35(10)
_cell_measurement_theta_max      20.6190
_cell_measurement_theta_min      3.9220
_cell_volume                     729.3(4)
_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)
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_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.35(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega   30.00   88.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000  -60.0000 29

  2 omega   38.00   88.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000 -180.0000 25

  3 omega  -20.00   16.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -30.0000 18

  4 omega  -16.00   48.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000  -90.0000 32

  5 omega  -48.00   32.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000   30.0000 40

  6 omega  -20.00   62.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000  120.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0867691000
_diffrn_orient_matrix_UB_12      -0.0442619000
_diffrn_orient_matrix_UB_13      0.0005426000
_diffrn_orient_matrix_UB_21      0.0820079000
_diffrn_orient_matrix_UB_22      -0.0613672000
_diffrn_orient_matrix_UB_23      0.0193604000
_diffrn_orient_matrix_UB_31      -0.0350222000
_diffrn_orient_matrix_UB_32      0.0013776000
_diffrn_orient_matrix_UB_33      0.0511525000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4855
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.291
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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.
;
_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    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0660
_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^)+(0.0630P)^2^+0.0648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1326
_reflns_number_total             2848
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00031_si_002.cif
_cod_data_source_block           wangchao0506
_cod_original_cell_volume        729.4(4)
_cod_database_code               4036613
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              53281
_shelx_hkl_checksum              84156
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-05-08
_olex2_submission_special_instructions 'No special instructions were received'