Synthesis of α-alkenylated nitriles <i>via</i> electrochemical generation of ketyl radicals.
Li, Kai; Yang, Hao; Zhang, Yupu; Sun, Qi; Wang, Zhiyong; Organic & biomolecular chemistry 24 (2026) 1346–1351; doi:10.1039/d5ob01801c

data_7160976
_publ_section_title
;
 Synthesis of &#x3b1;-alkenylated nitriles <i>via</i> electrochemical
 generation of ketyl radicals.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1346
_journal_page_last               1351
_journal_paper_doi               10.1039/d5ob01801c
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C15 H10 Br N'
_chemical_formula_sum            'C15 H10 Br N'
_chemical_formula_weight         284.15
_chemical_name_systematic        (Z)-2-(4-bromophenyl)-3-phenylacrylonitrile
_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     dual
_audit_creation_date             2025-12-14
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-12-17 deposited with the CCDC.	2026-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                116.987(4)
_cell_angle_beta                 92.240(5)
_cell_angle_gamma                101.866(4)
_cell_formula_units_Z            4
_cell_length_a                   6.8584(5)
_cell_length_b                   13.9916(9)
_cell_length_c                   14.6230(12)
_cell_measurement_reflns_used    7021
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      68.327
_cell_measurement_theta_min      3.650
_cell_volume                     1209.52(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14636
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.762
_diffrn_reflns_theta_min         3.431
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.408
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1559 before and 0.0814 after correction.
The Ratio of minimum to maximum transmission is 0.6334.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.250
_refine_diff_density_min         -0.886
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0691
_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^)+(0.0724P)^2^+5.6525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1914
_refine_ls_wR_factor_ref         0.2052
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3108
_reflns_number_total             4341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01801c2.cif
_cod_data_source_block           lk-1214-1
_cod_database_code               7160976
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.667
_shelx_estimated_absorpt_t_min   0.620
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C24(H24), C11(H11), C20(H20), C2(H2), C12(H12), C3(H3),
 C26(H26), C6(H6), C15(H15), C18(H18), C13(H13), C17(H17), C30(H30), C21(H21),
 C27(H27), C14(H14), C28(H28), C29(H29)
;
_shelx_res_checksum              66947
_olex2_submission_special_instructions 'No special instructions were received'