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_7241131
_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         'C25 H20 N2 S'
_chemical_formula_sum            'C25 H20 N2 S'
_chemical_formula_weight         380.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-22 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6915(2)
_cell_length_b                   12.7636(6)
_cell_length_c                   26.8264(12)
_cell_measurement_reflns_used    1658
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.7520
_cell_measurement_theta_min      3.8780
_cell_volume                     1948.78(14)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (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     14.00  79.00   1.00   16.00    --   17.77-135.00  62.00   65
  2  \w     -8.00  76.00   1.00   16.00    --   17.77  38.00  30.00   84
  3  \w     12.00  52.00   1.00   16.00    --  -19.57  19.00 -60.00   40
;
_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      0.0130531000
_diffrn_orient_matrix_UB_12      0.0549713000
_diffrn_orient_matrix_UB_13      -0.0028466000
_diffrn_orient_matrix_UB_21      0.0004318000
_diffrn_orient_matrix_UB_22      0.0060828000
_diffrn_orient_matrix_UB_23      0.0262682000
_diffrn_orient_matrix_UB_31      0.1239256000
_diffrn_orient_matrix_UB_32      -0.0058428000
_diffrn_orient_matrix_UB_33      0.0001875000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            7167
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.432
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62728
_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            Colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       Needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.0235P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.914
_reflns_number_gt                2720
_reflns_number_total             3830
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc02125c2.cif
_cod_data_source_block           20191007_pym_zpf_q_64aaa
_cod_depositor_comments
'Adding full bibliography for 7241129--7241131.cif.'
_cod_original_cell_volume        1948.80(15)
_cod_database_code               7241131
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.930
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C21(H21), C22(H22), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              59420
_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 1.482
_oxdiff_exptl_absorpt_empirical_full_min 0.751