Electrochemically enabled synthesis of sulfide imidazopyridines via a radical cyclization cascade
Zhong, Ping-Fu; Lin, Hong-Min; Wang, Lin-Wei; Mo, Zu-Yu; Meng, Xiu-Jin; Tang, Hai-Tao; Pan, Ying-Ming; Green Chemistry 22 (2020) 6334–6339; doi:10.1039/D0GC02125C

data_7241130
_publ_section_title
;
 Electrochemically enabled synthesis of sulfide imidazopyridines via a
 radical cyclization cascade
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              6334
_journal_page_last               6339
_journal_paper_doi               10.1039/D0GC02125C
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C22 H19 N3 O S, 0.75(C H4 O)'
_chemical_formula_sum            'C22.75 H22 N3 O1.75 S'
_chemical_formula_weight         397.49
_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
_audit_creation_date             2019-12-09
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2019-12-09 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.853(15)
_cell_angle_beta                 96.934(19)
_cell_angle_gamma                99.10(3)
_cell_formula_units_Z            2
_cell_length_a                   4.9241(18)
_cell_length_b                   14.209(4)
_cell_length_c                   15.2990(16)
_cell_measurement_reflns_used    1174
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.4610
_cell_measurement_theta_min      3.8590
_cell_volume                     1048.6(5)
_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    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -55.00  91.00   1.00   15.00    --   17.77   0.00-120.00  146
  2  \w    -20.00  60.00   1.00   15.00    --   17.77 -99.00-120.00   80
  3  \w      5.00  78.00   1.00   15.00    --   17.77-129.00  27.00   73
  4  \w    -90.00  10.00   1.00   15.00    --  -19.57 -77.00  60.00  100
  5  \w    -88.00   2.00   1.00   15.00    --  -19.57 -57.00 120.00   90
  6  \w     34.00  66.00   1.00   15.00    --   17.77-178.00-150.00   32
  7  \w    -26.00  91.00   1.00   15.00    --   17.77  19.00   0.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0172750000
_diffrn_orient_matrix_UB_12      -0.0463926000
_diffrn_orient_matrix_UB_13      -0.0197373000
_diffrn_orient_matrix_UB_21      -0.0090641000
_diffrn_orient_matrix_UB_22      0.0197705000
_diffrn_orient_matrix_UB_23      -0.0423499000
_diffrn_orient_matrix_UB_31      0.1457302000
_diffrn_orient_matrix_UB_32      0.0039550000
_diffrn_orient_matrix_UB_33      0.0009038000
_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  0.2226
_diffrn_reflns_av_unetI/netI     0.2078
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10064
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.713
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_min         3.888
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67479
_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    1.259
_exptl_crystal_description       needle
_exptl_crystal_F_000             419
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.892
_refine_ls_R_factor_all          0.2222
_refine_ls_R_factor_gt           0.1070
_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^)+(0.1128P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2312
_refine_ls_wR_factor_ref         0.3136
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1095
_reflns_number_total             3555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc02125c2.cif
_cod_data_source_block           20191108-mxjaaa
_cod_depositor_comments
'Adding full bibliography for 7241129--7241131.cif.'
_cod_database_code               7241130
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.931
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: O2(0.75) H2(0.75) C23(0.75) H23A(0.75) H23B(0.75) H23C(0.75)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17),
 C18(H18), C20(H20), C21(H21)
4.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
4.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              6574
_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 2.739
_oxdiff_exptl_absorpt_empirical_full_min 0.438