Phenyliodonium diacetate mediated carbotrifluoromethylation of N-acylhydrazones.
Zhang, Weigang; Su, Yingpeng; Chong, Siying; Wu, Lili; Cao, Guiyan; Huang, Danfeng; Wang, Ke-Hu; Hu, Yulai; Organic & biomolecular chemistry 14 (2016) 11162–11175; doi:10.1039/c6ob02041k

data_7155346
_publ_section_title
;
 Phenyliodonium diacetate mediated carbotrifluoromethylation of
 N-acylhydrazones.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              11162
_journal_page_last               11175
_journal_paper_doi               10.1039/c6ob02041k
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C15 H11 F3 N2 O'
_chemical_formula_sum            'C15 H11 F3 N2 O'
_chemical_formula_weight         292.26
_chemical_melting_point          416
_chemical_name_systematic
(E)-N'-(2,2,2-Trifluoro-1-phenylethylidene)benzohydrazide
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-05-26 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.665(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7064(5)
_cell_length_b                   17.0772(13)
_cell_length_c                   14.1572(9)
_cell_measurement_reflns_used    1029
_cell_measurement_temperature    293.69(16)
_cell_measurement_theta_max      21.3220
_cell_measurement_theta_min      3.7340
_cell_volume                     1375.04(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      293.69(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -5.00   37.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       27.1670   57.0000   60.0000 28

  2 omega  -17.00   55.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       27.1670  -99.0000   90.0000 48

  3 omega   -5.00   92.50   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       27.1670   57.0000 -180.0000 65

  4 omega -112.00  -70.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -23.9639  178.0000  150.0000 28
;
_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      0.0167852000
_diffrn_orient_matrix_UB_12      -0.0058405000
_diffrn_orient_matrix_UB_13      0.0497021000
_diffrn_orient_matrix_UB_21      0.0309523000
_diffrn_orient_matrix_UB_22      0.0399830000
_diffrn_orient_matrix_UB_23      0.0061991000
_diffrn_orient_matrix_UB_31      -0.1196867000
_diffrn_orient_matrix_UB_32      0.0095412000
_diffrn_orient_matrix_UB_33      0.0042928000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4969
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.58
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.0867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1527
_reflns_number_gt                1437
_reflns_number_total             2697
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02041k2.cif
_cod_data_source_block           zhangwg_0524_1
_cod_depositor_comments
'Adding full bibliography for 7155345--7155346.cif.'
_cod_database_code               7155346
_reflns_odcompleteness_completeness 99.73
_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 N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
  C14(H14), C15(H15)
;
_olex2_date_sample_data_collection 2016-05-24
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method
'petroleum ether/ dichloromethane'