Electrochemical formation of N,N'-diarylhydrazines by dehydrogenative N-N homocoupling reaction.
Breising, Valentina M.; Kayser, Jacob M.; Kehl, Anton; Schollmeyer, Dieter; Liermann, Johannes C.; Waldvogel, Siegfried R.; Chemical communications (Cambridge, England) 56 (2020) 4348–4351; doi:10.1039/d0cc01052a

data_7126175
_publ_section_title
;
 Electrochemical formation of N,N'-diarylhydrazines by dehydrogenative N-N
 homocoupling reaction.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4348
_journal_page_last               4351
_journal_paper_doi               10.1039/d0cc01052a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C18 H14 F6 N2 O2'
_chemical_formula_sum            'C18 H14 F6 N2 O2'
_chemical_formula_weight         404.31
_chemical_name_systematic
;
N,N'-Diacetyl-N,N'-di(4-trifluoromethylphenyl)-hydrazine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-01-21 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_a                   10.8529(9)
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_cell_measurement_reflns_used    5434
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.47
_cell_volume                     1894.0(3)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      ' 158 frames, detector distance = 70 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5435
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.242
_diffrn_reflns_theta_min         2.880
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.133
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_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 449 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0346P)^2^+1.1395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                1555
_reflns_number_total             2298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01052a2.cif
_cod_data_source_block           vbrjka4
_cod_depositor_comments          'Adding full bibliography for 7126175.cif.'
_cod_database_code               7126175
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              9211