Electrochemical oxidative thioetherification of aldehyde hydrazones with thiophenols.
Hu, Meiqian; Yang, Xiaolin; Zhang, Shuai; Qin, Changsheng; Zhang, Zhihua; Wang, Jingfang; Ji, Fanghua; Jiang, Guangbin; Organic & biomolecular chemistry 22 (2024) 5907–5912; doi:10.1039/d4ob00833b

data_7160021
_publ_section_title
;
 Electrochemical oxidative thioetherification of aldehyde hydrazones with
 thiophenols.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5907
_journal_page_last               5912
_journal_paper_doi               10.1039/d4ob00833b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C17 H17 Cl N2 O S'
_chemical_formula_sum            'C17 H18 Cl N2 O S'
_chemical_formula_weight         333.84
_chemical_name_systematic        z
_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
_audit_creation_date             2023-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-10-25 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.995(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3567(2)
_cell_length_b                   14.2027(5)
_cell_length_c                   21.0025(8)
_cell_measurement_reflns_used    5711
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      29.1170
_cell_measurement_theta_min      1.6780
_cell_volume                     1597.62(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.808
_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    -25.00  93.00   0.50    0.33    --   10.68  27.00-101.00  236
  2  \w     19.00  55.00   0.50    0.33    --   10.68 -99.00 -30.00   72
  3  \w     15.00  41.00   0.50    0.33    --   10.68 -99.00  30.00   52
  4  \w    -71.00  -5.00   0.50    0.33    --   10.68 -27.00  96.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1220090000
_diffrn_orient_matrix_UB_12      0.0178698000
_diffrn_orient_matrix_UB_13      -0.0056409000
_diffrn_orient_matrix_UB_21      -0.0221234000
_diffrn_orient_matrix_UB_22      -0.0007437000
_diffrn_orient_matrix_UB_23      0.0331946000
_diffrn_orient_matrix_UB_31      0.0464870000
_diffrn_orient_matrix_UB_32      0.0466301000
_diffrn_orient_matrix_UB_33      0.0026977000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9512
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.115
_diffrn_reflns_theta_min         1.731
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             700
_exptl_crystal_preparation       1
_exptl_crystal_recrystallization_method 1
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          1
_exptl_crystal_size_min          1
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0402P)^2^+0.6835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0949
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2809
_reflns_number_total             3476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00833b2.cif
_cod_data_source_block           6582-hmq-100k_auto
_cod_depositor_comments          'Adding full bibliography for 7160021.cif.'
_cod_database_code               7160021
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.707
_shelx_estimated_absorpt_t_min   0.707
_diffrn_oxdiff_digest_frames
;
0137f77d6775d7a1a7744287a036ff6d2c00042f91c
;
_diffrn_oxdiff_digest_hkl
;
01b36f1d223591cf6ddc298117268acedc6826
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00D(H00E,H00F), C00H(H00J,H00K), C00L(H00N,H00O)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00D), C00E(H00G), C00F(H00H), C00G(H00I),
 C00I(H00L), C00K(H00M), C00M(H00P)
;
_shelx_res_checksum              17632
_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 1.430
_oxdiff_exptl_absorpt_empirical_full_min 0.624