Copper-Catalyzed β-Trifluoromethylation of Conjugated Hydrazones.
Prieto, Alexis; Jeamet, Emeric; Monteiro, Nuno; Bouyssi, Didier; Baudoin, Olivier; Organic letters 16 (2014) 4770–4773; doi:10.1021/ol5022228

data_1517564
_publ_section_title
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 Copper-Catalyzed \b-Trifluoromethylation of Conjugated Hydrazones.
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_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4770
_journal_page_last               4773
_journal_paper_doi               10.1021/ol5022228
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H19 F3 N2 O1'
_chemical_formula_sum            'C24 H19 F3 N2 O'
_chemical_formula_weight         408.42
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   8.7161(4)
_cell_length_b                   44.918(2)
_cell_length_c                   5.2061(3)
_cell_measurement_reflns_used    2553
_cell_measurement_temperature    293
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     2038.24(18)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -61
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8826
_diffrn_reflns_theta_full        25.278
_diffrn_reflns_theta_max         29.056
_diffrn_reflns_theta_min         2.958
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.872
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.21
_refine_ls_abs_structure_details 'Flack (1983), 2523 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.1(13)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.2169
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         2575
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.0048019
_refine_ls_shift/su_mean         0.0003853
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 3.43 -0.941 2.60 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0545
_refine_ls_wR_factor_gt          0.0466
_refine_ls_wR_factor_ref         0.0437
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              61
_reflns_limit_k_min              0
_reflns_limit_l_max              5
_reflns_limit_l_min              -7
_reflns_number_gt                3113
_reflns_number_total             4342
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.46
_oxford_diffrn_Wilson_scale      0.28
_oxford_refine_ls_r_factor_ref   0.0502
_oxford_refine_ls_scale          2.481(5)
_oxford_reflns_number_all        4335
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            ol5022228_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1517564--1517565.cif.'
_cod_original_cell_volume        2038.22(19)
_cod_original_sg_symbol_H-M      'P n a 21 '
_cod_original_formula_sum        'C24 H19 F3 N2 O1'
_cod_database_code               1517564
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
END                                                                             
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_iucr_refine_instruction_details_restraints
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NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.010000 = F(1) TO C(2) 
U(IJ)'S  0.0, 0.010000 = C(2) TO F(4) 
END                                                                             
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