Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids.
Tan, Xinqiang; Liu, Zhonglin; Shen, Haigen; Zhang, Pei; Zhang, Zhenzhen; Li, Chaozhong; Journal of the American Chemical Society 139 (2017) 12430–12433; doi:10.1021/jacs.7b07944

data_4131650
_publ_section_title
;
 Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic
 Carboxylic Acids.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12430
_journal_page_last               12433
_journal_paper_doi               10.1021/jacs.7b07944
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C4 H3 Cu F9, C16 H36 N'
_chemical_formula_sum            'C20 H39 Cu F9 N'
_chemical_formula_weight         528.06
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                100.003(2)
_cell_angle_beta                 96.765(2)
_cell_angle_gamma                104.964(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8347(6)
_cell_length_b                   10.9173(7)
_cell_length_c                   13.2494(8)
_cell_measurement_reflns_used    6074
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      27.449
_cell_measurement_theta_min      2.175
_cell_volume                     1333.51(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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_temperature      301.44
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0434
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18526
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.463
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1328 before and 0.0494 after correction. The Ratio of minimum to maximum transmission is 0.8557. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.344
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4844
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0981
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1997P)^2^+0.6597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2594
_refine_ls_wR_factor_ref         0.3027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3281
_reflns_number_total             4844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07944_si_001.cif
_cod_data_source_block           mo_d8v17092_0m
_cod_database_code               4131650
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.901
_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. Restrained distances
 F6-C2 = F5-C2 = F4-C2 = F1-C1 = F3-C1 = F2-C1 = F8-C3 = F9-C3 = F7-C3
 1.38 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F5 \\sim F4 \\sim F6 \\sim C2: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.01
F2 \\sim F1 \\sim F3 \\sim C1: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.01
F9 \\sim F7 \\sim F8 \\sim C3: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B),
 C18(H18A,H18B), C19(H19A,H19B)
4.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C16(H16A,H16B,H16C),
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              5946
_shelx_hkl_checksum              80776
_olex2_submission_special_instructions 'No special instructions were received'