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_7244948
_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 H17 N O2 S'
_chemical_formula_sum            'C22 H17 N O2 S'
_chemical_formula_weight         359.42
_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             2021-06-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-21 deposited with the CCDC.	2022-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.991(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5262(4)
_cell_length_b                   5.4497(2)
_cell_length_c                   25.0014(9)
_cell_measurement_reflns_used    9692
_cell_measurement_temperature    170.01(10)
_cell_measurement_theta_max      31.1330
_cell_measurement_theta_min      1.6150
_cell_volume                     1702.56(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.860
_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  94.00   0.50    8.00    --    5.00  45.00 120.00   50
  2  \w     24.00  50.00   0.50    8.00    --    5.00  45.00 120.00   52
  3  \w     43.00  69.00   0.50    8.00    --    5.00  45.00 150.00   52
  4  \w    -53.00 -27.00   0.50    8.00    --  -11.60  45.00 175.30   52
  5  \w     27.00  77.00   0.50    8.00    --  -11.60  45.00 175.30  100
  6  \w   -101.00 -76.00   0.50    8.00    --  -11.60  45.00 175.30   50
  7  \w    -89.00  76.00   0.50    8.00    --  -11.60  45.00 -15.90  330
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0262311000
_diffrn_orient_matrix_UB_12      -0.0932960000
_diffrn_orient_matrix_UB_13      -0.0139464000
_diffrn_orient_matrix_UB_21      -0.0161613000
_diffrn_orient_matrix_UB_22      -0.0881777000
_diffrn_orient_matrix_UB_23      0.0186452000
_diffrn_orient_matrix_UB_31      -0.0476609000
_diffrn_orient_matrix_UB_32      -0.0213513000
_diffrn_orient_matrix_UB_33      -0.0163449000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16068
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.790
_diffrn_reflns_theta_min         1.633
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45i (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    1.402
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0538P)^2^+0.4977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3986
_reflns_number_total             4571
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc00151a2.cif
_cod_data_source_block           mx9460
_cod_depositor_comments
'Adding full bibliography for 7244947--7244948.cif.'
_cod_database_code               7244948
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOS
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              67106
_shelx_hkl_checksum              97923
_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 1.538
_oxdiff_exptl_absorpt_empirical_full_min 0.533