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_7155345
_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         'C14 H10 N2 O'
_chemical_formula_sum            'C14 H10 N2 O'
_chemical_formula_weight         222.24
_chemical_melting_point          410
_chemical_name_systematic        2,5-diphenyl-1,3,4-oxadiazole
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2016-05-25 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.142(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1901(6)
_cell_length_b                   18.063(3)
_cell_length_c                   12.1410(13)
_cell_measurement_reflns_used    289
_cell_measurement_temperature    293.18(10)
_cell_measurement_theta_max      19.3030
_cell_measurement_theta_min      4.0370
_cell_volume                     1136.5(3)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -20.00   24.00   2.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916  -99.0000  -60.0000 22

  2 omega   -9.00   53.00   2.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291  -99.0000  120.0000 31

  3 omega  -24.00   78.00   2.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   19.0000   90.0000 51
;
_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      0.0235408000
_diffrn_orient_matrix_UB_12      0.0192164000
_diffrn_orient_matrix_UB_13      0.0504803000
_diffrn_orient_matrix_UB_21      -0.0252796000
_diffrn_orient_matrix_UB_22      0.0340988000
_diffrn_orient_matrix_UB_23      -0.0275212000
_diffrn_orient_matrix_UB_31      -0.1324498000
_diffrn_orient_matrix_UB_32      -0.0030948000
_diffrn_orient_matrix_UB_33      0.0108786000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.2044
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4110
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.36
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60274
_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    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.2476
_refine_ls_R_factor_gt           0.0946
_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^)+(0.0494P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.2374
_reflns_number_gt                765
_reflns_number_total             2240
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02041k2.cif
_cod_data_source_block           zwj_0521
_cod_depositor_comments
'Adding full bibliography for 7155345--7155346.cif.'
_cod_database_code               7155345
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 c5(H5), c14(H14), c1(H1), c3(H3), c2(H2), c10(H10), c11(H11), c4(H4),
 c12(H12), c13(H13)
;
_olex2_date_sample_data_collection 2015-05-21
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method
'dichloromethane/petroleum ether'