Electrochemical amidochlorination between low-cost styrenes and amides.
Liang, Xing-An; Chen, Qi-An; Wu, Weiying; Li, Yuzhen; Cheng, Yani; Huang, Mingyan; Mo, Shihua; Organic & biomolecular chemistry 23 (2025) 6610–6615; doi:10.1039/d5ob00874c

data_7160608
_publ_section_title
;
 Electrochemical amidochlorination between low-cost styrenes and amides.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6610
_journal_page_last               6615
_journal_paper_doi               10.1039/d5ob00874c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C15 H13 Cl F N O'
_chemical_formula_sum            'C15 H13 Cl F N O'
_chemical_formula_weight         277.71
_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             2020-06-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-02-09 deposited with the CCDC.	2025-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                80.540(3)
_cell_angle_beta                 87.394(3)
_cell_angle_gamma                81.359(2)
_cell_formula_units_Z            2
_cell_length_a                   5.1084(2)
_cell_length_b                   10.9354(3)
_cell_length_c                   12.2655(4)
_cell_measurement_reflns_used    4430
_cell_measurement_temperature    249.99(10)
_cell_measurement_theta_max      70.7110
_cell_measurement_theta_min      3.6270
_cell_volume                     668.04(4)
_computing_cell_refinement
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_collection
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_reduction
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      249.99(10)
_diffrn_detector                 'Hybrid Pixel Counting (HPC) detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HyPix-6000HE'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    -82.00  43.00   0.50    0.50    --    5.00 -38.00-150.00  250
  2  \w    -46.00 -20.00   0.50    0.50    --  -47.30 -57.00 -30.00   52
  3  \w    -84.00  37.00   0.50    0.50    --  -47.30  38.00  90.00  242
  4  \w   -117.00 -83.00   0.50    0.50    --  -47.30 -57.00 -30.00   68
  5  \w    -66.00  -8.00   0.50    0.50    --  -47.30 -75.00-180.00  116
  6  \w   -120.00 -82.00   0.50    0.50    --  -47.30 -75.00-180.00   76
  7  \w    -90.00  -9.00   0.50    0.50    --  -47.30 -75.00  30.00  162
  8  \w    -60.00 -29.00   0.50    0.50    --  -68.00 -75.00 -37.76   62
  9  \w    -64.00 -38.00   0.50    0.71    --  -76.00 -75.00 121.76   52
 10  \w    -71.00 -40.00   0.50    0.71    --  -76.00 -72.00  51.68   62
 11  \w    -66.00 -37.00   0.50    0.71    --  -76.00 -75.00 151.99   58
 12  \w    -69.00 -43.00   0.50    0.71    --  -80.00 -70.00  77.75   52
 13  \w    -73.00 -42.00   0.50    0.71    --  -80.00 -74.00 -73.36   62
 14  \w   -130.00-104.00   0.50    0.71    --  -80.00 -74.00 -73.36   52
 15  \w    -77.00 -48.00   0.50    0.71    --  -84.00 -68.00   2.47   58
 16  \w   -151.00-112.00   0.50    0.71    --  -84.00 -68.00   2.47   78
 17  \w   -170.00-138.00   0.50    0.71    --  -88.00 -73.00 -23.01   64
 18  \w   -113.00 -87.00   0.50    0.71    --  -88.00 -60.00-152.22   52
 19  \w   -140.00 -54.00   0.50    0.71    --  -88.00 -61.00-120.01  172
 20  \w   -121.00 -61.00   0.50    0.71    --  -88.00 -63.00 108.81  120
 21  \w   -169.00 -50.00   0.50    0.71    --  -88.00 -75.00 -36.39  238
 22  \w   -176.00-146.00   0.50    0.71    --  -88.00 -61.00-120.01   60
 23  \w    -83.00 -50.00   0.50    0.71    --  -88.00 -73.00 -23.01   66
 24  \w   -131.00 -86.00   0.50    0.71    --  -88.00 -73.00 -23.01   90
 25  \w    -81.00 -54.00   0.50    0.71    --  -88.00 -60.00-152.22   54
 26  \w    -97.00 -60.00   0.50    0.71    --  -92.00 -57.00-170.22   74
 27  \w   -181.00-103.00   0.50    0.71    --  -92.00 -57.00-170.22  156
 28  \w   -185.00 -62.00   0.50    0.71    --  -96.70 -57.00 120.00  246
 29  \w   -128.00 -59.00   0.50    0.71    --  -96.70  75.00-180.00  138
 30  \w   -132.00 -46.00   0.50    0.71    --  -96.70  75.00 -30.00  172
 31  \w   -185.00 -64.00   0.50    0.71    --  -96.70 -57.00  30.00  242
 32  \w   -181.00 -60.00   0.50    0.71    --  -96.70 -75.00 -68.24  242
 33  \w    -67.00 -42.00   0.50    0.71    --  -96.70  75.00  90.00   50
 34  \w   -107.00 -78.00   0.50    0.71    --  -96.70  75.00  90.00   58
 35  \w    -53.00  -7.00   0.50    0.71    --  -96.70  75.00 -90.00   92
 36  \w   -132.00 -62.00   0.50    0.71    --  -96.70  75.00 -90.00  140
 37  \w   -131.00 -13.00   0.50    0.71    --  -96.70  75.00  30.00  236
 38  \w   -105.00 -57.00   0.50    0.71    --  -96.70 -75.00-180.00   96
 39  \w   -150.00-109.00   0.50    0.71    --  -96.70 -75.00-180.00   82
 40  \w   -179.00 -62.00   0.50    0.71    --  -96.70 -56.00  53.97  234
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'profile data from \w-scans and \phi-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0031882000
_diffrn_orient_matrix_UB_12      0.0340235000
_diffrn_orient_matrix_UB_13      -0.1269770000
_diffrn_orient_matrix_UB_21      -0.0396119000
_diffrn_orient_matrix_UB_22      -0.1347192000
_diffrn_orient_matrix_UB_23      -0.0095352000
_diffrn_orient_matrix_UB_31      -0.3025051000
_diffrn_orient_matrix_UB_32      0.0390936000
_diffrn_orient_matrix_UB_33      0.0026470000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'VariMax VHF'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11194
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        64.995
_diffrn_reflns_theta_max         64.995
_diffrn_reflns_theta_min         3.654
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    2.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.295
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0737
_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^)+(0.1149P)^2^+0.5755P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2100
_refine_ls_wR_factor_ref         0.2170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1934
_reflns_number_total             2248
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00874c2.cif
_cod_data_source_block           liangxinan-lxa-20200622-250k
_cod_depositor_comments          'Adding full bibliography for 7160608.cif.'
_cod_database_code               7160608
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'H C N O F'
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.821
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5), C7(H7), C4(H4), C14(H14), C15(H15), C6(H6), C11(H11),
 C12(H12)
;
_shelx_res_checksum              73847
_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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.733