Switching between α-alkenylation and α-alkylation of nitriles by coupling multiple electrochemical methods
Li, Kai; Li, Tong; Zhang, Yupu; Yang, Hao; Sun, Qi; Wang, Zhiyong; Green Chemistry 27 (2025) 6734–6740; doi:10.1039/D5GC01206F

data_7250419
_publ_section_title
;
 Switching between \a-alkenylation and \a-alkylation of nitriles by
 coupling multiple electrochemical methods
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              6734
_journal_page_last               6740
_journal_paper_doi               10.1039/D5GC01206F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C14 H12 N2 O'
_chemical_formula_sum            'C14 H12 N2 O'
_chemical_formula_weight         224.26
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-05-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-02-19 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.743(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0084(3)
_cell_length_b                   8.7513(2)
_cell_length_c                   15.7194(4)
_cell_measurement_reflns_used    2231
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8420
_cell_measurement_theta_min      5.7100
_cell_volume                     1221.37(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -124.00  41.00   1.00    2.00    --  -40.01   0.00-120.00  165
  2  \w     71.00  98.00   1.00    2.00    --   40.01 178.00-150.00   27
  3  \w    -19.00  16.00   1.00    2.00    --   40.01 -77.00  30.00   35
  4  \w    150.00 177.00   1.00    4.00    --  105.74  77.00   0.00   27
  5  \w     90.00 177.00   1.00    4.00    --  105.74  45.00  30.00   87
  6  \w     73.00 111.00   1.00    4.00    --  105.74-125.00-120.00   38
  7  \w    120.00 147.00   1.00    4.00    --  105.74  77.00 -90.00   27
  8  \w    130.00 167.00   1.00    4.00    --  105.74 125.00 -60.00   37
  9  \w     33.00 130.00   1.00    4.00    --  105.74 -61.00-120.00   97
 10  \w    108.00 175.00   1.00    4.00    --  105.74  77.00 -30.00   67
 11  \w    112.00 157.00   1.00    4.00    --  105.74  77.00 -60.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0181536000
_diffrn_orient_matrix_UB_12      -0.0881697000
_diffrn_orient_matrix_UB_13      0.0859047000
_diffrn_orient_matrix_UB_21      0.1658784000
_diffrn_orient_matrix_UB_22      0.0507172000
_diffrn_orient_matrix_UB_23      0.0212681000
_diffrn_orient_matrix_UB_31      -0.0474548000
_diffrn_orient_matrix_UB_32      0.1437023000
_diffrn_orient_matrix_UB_33      0.0453871000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4213
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.887
_diffrn_reflns_theta_min         4.981
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0474P)^2^+0.1449P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1887
_reflns_number_total             2345
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc01206f2.cif
_cod_data_source_block           lk-2-ea_auto
_cod_depositor_comments          'Adding full bibliography for 7250419.cif.'
_cod_database_code               7250419
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         c20h20n2o2
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.874
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C8(H8), C7(H7)
1.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C5(H5), C13(H13), C12(H12), C2(H2), C6(H6), C11(H11), C1(H1A)
1.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              51849
_shelx_hkl_checksum              12926
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.776