Electroreductive synthesis of polyfunctionalized pyridin-2-ones from acetoacetanilides and carbon disulfide with oxygen evolution.
Xu, Lichun; Ma, Zhongxiao; Hu, Xi; Zhang, Xin; Gao, Shulin; Liang, Deqiang; Wang, Baoling; Li, Weili; Li, Yanni; Organic & biomolecular chemistry 20 (2022) 1013–1018; doi:10.1039/d1ob02379a

data_7158483
_publ_section_title
;
 Electroreductive synthesis of polyfunctionalized pyridin-2-ones from
 acetoacetanilides and carbon disulfide with oxygen evolution.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1013
_journal_page_last               1018
_journal_paper_doi               10.1039/d1ob02379a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C21 H18 N2 O3'
_chemical_formula_sum            'C21 H18 N2 O3'
_chemical_formula_weight         346.37
_chemical_name_systematic
5-acetyl-2-methyl-6-oxo-N,1-diphenyl-1,6-dihydropyridine-3-carboxamide
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-09-11
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2021-10-07 deposited with the CCDC.	2022-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                92.542(8)
_cell_angle_beta                 98.729(10)
_cell_angle_gamma                97.055(9)
_cell_formula_units_Z            2
_cell_length_a                   8.1439(10)
_cell_length_b                   9.6588(8)
_cell_length_c                   11.5840(13)
_cell_measurement_reflns_used    2034
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5730
_cell_measurement_theta_min      3.8780
_cell_volume                     891.98(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9925
_diffrn_measured_fraction_theta_max 0.9731
_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    -69.00 -43.00   1.00    1.00    --    0.00 -57.00 -90.00   26
  2  \w    -30.00  -4.00   1.00    1.00    --    0.00 -57.00 -90.00   26
  3  \w     -8.00  21.00   1.00    1.00    --    0.00  57.00  30.00   29
  4  \w     39.00  66.00   1.00    1.00    --    0.00  57.00  30.00   27
  5  \w    -16.00  11.00   1.00    1.00    --   54.00 -19.00 -60.00   27
  6  \w      1.00  74.00   1.00    1.00    --   54.00 -57.00 -60.00   73
  7  \w     30.00 126.00   1.00    1.00    --   54.00  37.00 120.00   96
  8  \w     41.00 106.00   1.00    1.00    --   54.00-125.00 150.00   65
  9  \w     16.00  67.00   1.00    1.00    --   54.00 -19.00 -60.00   51
 10  \w     -5.00  39.00   1.00    1.00    --   54.00 -57.00 150.00   44
 11  \w    -10.00  71.00   1.00    1.00    --   54.00 -57.00-150.00   81
 12  \w     66.00 105.00   1.00    1.00    --  108.00-111.00-120.00   39
 13  \w     86.00 175.00   1.00    1.00    --  108.00  37.00   0.00   89
 14  \w    103.00 174.00   1.00    1.00    --  108.00 111.00-180.00   71
 15  \w     65.00 100.00   1.00    1.00    --  108.00 -25.00  90.00   35
 16  \w     73.00 103.00   1.00    1.00    --  108.00-111.00 -30.00   30
 17  \w     88.00 168.00   1.00    1.00    --  108.00  50.00-120.00   80
 18  \w    142.00 172.00   1.00    1.00    --  108.00  50.00 -90.00   30
 19  \w     90.00 124.00   1.00    1.00    --  108.00  50.00 -90.00   34
 20  \w     40.00 126.00   1.00    1.00    --  108.00 -63.00-150.00   86
 21  \w     92.00 173.00   1.00    1.00    --  108.00  50.00 -60.00   81
 22  \w     44.00 108.00   1.00    1.00    --  108.00-111.00  30.00   64
 23  \w     65.00 112.00   1.00    1.00    --  108.00-111.00 120.00   47
 24  \w     37.00  63.00   1.00    1.00    --  108.00-111.00 120.00   26
 25  \w     71.00 116.00   1.00    1.00    --  108.00 178.00 120.00   45
 26  \w     40.00 130.00   1.00    1.00    --  108.00 -63.00  90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0993267000
_diffrn_orient_matrix_UB_12      0.1158295000
_diffrn_orient_matrix_UB_13      0.0880988000
_diffrn_orient_matrix_UB_21      0.1406800000
_diffrn_orient_matrix_UB_22      0.0159053000
_diffrn_orient_matrix_UB_23      -0.0754755000
_diffrn_orient_matrix_UB_31      -0.0872524000
_diffrn_orient_matrix_UB_32      0.1107549000
_diffrn_orient_matrix_UB_33      -0.0687062000
_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     0.0227
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5461
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.87
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0069(9)
_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   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0635P)^2^+0.1338P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                2613
_reflns_number_total             3166
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob02379a2.cif
_cod_data_source_block           exp_3536
_cod_depositor_comments          'Adding full bibliography for 7158483.cif.'
_cod_database_code               7158483
_reflns_odcompleteness_completeness 99.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 C14(H1A)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.791