Electrochemical Difluoromethylarylation of Alkynes.
Xiong, Peng; Xu, He-Huan; Song, Jinshuai; Xu, Hai-Chao; Journal of the American Chemical Society 140 (2018) 2460–2464; doi:10.1021/jacs.8b00391

data_4132026
_publ_section_title
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 Electrochemical Difluoromethylarylation of Alkynes.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2460
_journal_page_last               2464
_journal_paper_doi               10.1021/jacs.8b00391
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C19 H14 F5 N O'
_chemical_formula_sum            'C19 H14 F5 N O'
_chemical_formula_weight         367.31
_chemical_name_systematic        x0918
_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     iterative
_audit_creation_date             2017-09-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                84.008(5)
_cell_angle_beta                 79.819(5)
_cell_angle_gamma                79.127(5)
_cell_formula_units_Z            2
_cell_length_a                   7.923(2)
_cell_length_b                   9.918(3)
_cell_length_c                   10.534(3)
_cell_measurement_reflns_used    3821
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      28.88
_cell_measurement_theta_min      2.65
_cell_volume                     797.9(4)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7048
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.884
_diffrn_reflns_theta_min         1.969
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.846753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.1075 before and 0.0227 after correction.
The Ratio of minimum to maximum transmission is 0.8468.
The \l/2 correction factor is 0.0015.
;
_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    1.529
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.87
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0734P)^2^+0.2863P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1459
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3154
_reflns_number_total             3689
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b00391_si_002.cif
_cod_data_source_block           x0918m
_cod_original_cell_volume        798.0(4)
_cod_database_code               4132026
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.892
_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 Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C16(H16), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'