An approach for the synthesis of 2-aryl-3-sulfonyl substituted quinolines through an electrochemical cascade annulation pathway
Ma, Qiang; Li, Ming; Chen, Zhuo; Ni, Shao-Fei; Wright, James S.; Wen, Li-Rong; Zhang, Lin-Bao; Green Chemistry 24 (2022) 4425–4431; doi:10.1039/D2GC00151A

data_7244947
_publ_section_title
;
 An approach for the synthesis of 2-aryl-3-sulfonyl substituted quinolines
 through an electrochemical cascade annulation pathway
;
_journal_issue                   11
_journal_name_full               'Green Chemistry'
_journal_page_first              4425
_journal_page_last               4431
_journal_paper_doi               10.1039/D2GC00151A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C22 H15 F2 N O2 S'
_chemical_formula_sum            'C22 H15 F2 N O2 S'
_chemical_formula_weight         395.41
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-06 deposited with the CCDC.	2022-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.8360(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.72729(8)
_cell_length_b                   5.56880(5)
_cell_length_c                   25.1187(2)
_cell_measurement_reflns_used    18311
_cell_measurement_temperature    169.99(11)
_cell_measurement_theta_max      75.3410
_cell_measurement_theta_min      3.4690
_cell_volume                     1778.13(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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      169.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_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   -114.00 -65.00   0.50    0.05    --  -47.20-138.00  95.00   98
  2  \w    -95.00 -19.00   0.50    0.05    --  -47.20 131.00 -18.00  152
  3  \w   -119.00 -94.00   0.50    0.05    --  -47.20-131.00 -89.00   50
  4  \w    -85.00 -60.00   0.50    0.05    --  -47.20 138.00 156.00   50
  5  \w     60.00  90.00   0.50    0.05    --   47.20-131.00 -89.00   60
  6  \w   -121.00 -67.00   0.50    0.05    --  -99.00 138.00 156.00  108
  7  \w    -73.00 -47.00   0.50    0.05    --  -99.00 131.00 -18.00   52
  8  \w     76.00 101.00   0.50    0.05    --  103.25-138.00  95.00   50
  9  \w     72.00 144.00   0.50    0.05    --  103.25 138.00 156.00  144
 10  \w     65.00  91.00   0.50    0.05    --  103.25-131.00 -89.00   52
 11  \w     85.00 124.00   0.50    0.05    --  103.25 131.00 -18.00   78
 12  \w   -112.00 -74.00   0.50    0.05    --  -47.20-125.00 -60.00   76
 13  \w    -23.00  28.00   0.50    0.05    --  -47.20  19.00 150.00  102
 14  \w    -23.00  24.00   0.50    0.05    --  -47.20  19.00 -60.00   94
 15  \w   -113.00 -82.00   0.50    0.05    --  -47.20-125.00-120.00   62
 16  \w    -23.00  28.00   0.50    0.05    --  -47.20  19.00-150.00  102
 17  \w   -107.00 -77.00   0.50    0.05    --  -47.20-125.00 120.00   60
 18  \w     49.00 113.00   0.50    0.05    --   47.20  77.00  60.00  128
 19  \w   -126.00 -91.00   0.50    0.05    --  -99.00 144.00 -36.87   70
 20  \w   -112.00 -52.00   0.50    0.05    --  -99.00 125.00  60.00  120
 21  \w   -125.00 -80.00   0.50    0.05    --  -99.00 143.00-170.16   90
 22  \w   -168.00-112.00   0.50    0.05    --  -99.00 -53.00  94.39  112
 23  \w   -112.00 -50.00   0.50    0.05    --  -99.00 125.00  30.00  124
 24  \w   -167.00 -79.00   0.50    0.05    --  -99.00 -73.00   3.72  176
 25  \w    -55.00 -28.00   0.50    0.05    --  -99.00  61.00   0.00   54
 26  \w    -51.00 -26.00   0.50    0.05    --  -99.00  61.00  30.00   50
 27  \w   -168.00 -82.00   0.50    0.05    --  -99.00 -61.00-180.00  172
 28  \w    -73.00 -32.00   0.50    0.05    --  -99.00 125.00 -90.00   82
 29  \w   -110.00 -84.00   0.50    0.05    --  -99.00 125.00 -90.00   52
 30  \w    -85.00 -59.00   0.50    0.05    --  -99.00  77.00-180.00   52
 31  \w   -112.00 -86.00   0.50    0.05    --  -99.00 125.00  90.00   52
 32  \w    -52.00 -27.00   0.50    0.05    --  -99.00  61.00-150.00   50
 33  \w   -168.00 -91.00   0.50    0.05    --  -99.00 -64.00 -78.74  154
 34  \w   -131.00 -51.00   0.50    0.05    --  -99.00 153.00  70.49  160
 35  \w     31.00  74.00   0.50    0.05    --  103.25 -61.00  60.00   86
 36  \w     31.00  75.00   0.50    0.05    --  103.25 -61.00-180.00   88
 37  \w     56.00 106.00   0.50    0.05    --  103.25 -94.00 -60.00  100
 38  \w     31.00 109.00   0.50    0.05    --  103.25 -77.00 -30.00  156
 39  \w     32.00  99.00   0.50    0.05    --  103.25 -94.00-180.00  134
 40  \w     33.00  74.00   0.50    0.05    --  103.25 -61.00  90.00   82
 41  \w     35.00 111.00   0.50    0.05    --  103.25-125.00 -30.00  152
 42  \w     32.00  68.00   0.50    0.05    --  103.25 -61.00-120.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0061524000
_diffrn_orient_matrix_UB_12      -0.1614287000
_diffrn_orient_matrix_UB_13      -0.0498597000
_diffrn_orient_matrix_UB_21      -0.0079737000
_diffrn_orient_matrix_UB_22      0.2245977000
_diffrn_orient_matrix_UB_23      -0.0357924000
_diffrn_orient_matrix_UB_31      0.1207639000
_diffrn_orient_matrix_UB_32      0.0065974000
_diffrn_orient_matrix_UB_33      -0.0018564000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23427
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.508
_diffrn_reflns_theta_min         3.477
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.965
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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    1.477
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.7506P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3459
_reflns_number_total             3571
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc00151a2.cif
_cod_data_source_block           tx2992
_cod_depositor_comments
'Adding full bibliography for 7244947--7244948.cif.'
_cod_original_cell_volume        1778.12(2)
_cod_database_code               7244947
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOFS
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              95196
_shelx_hkl_checksum              44703
_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 1.463
_oxdiff_exptl_absorpt_empirical_full_min 0.650