Electrochemical oxidative regio- and stereo-selective thio(seleno)cyanation of enamides and mechanistic insights
Gu, Qingyun; Cheng, Zhenfeng; Xiong, Xing; Xiong, Biao; Zhao, Yu; Xu, Hua-Dong; Zhang, Yanan; Qiu, Xiaodong; Zeng, Xiaobao; Green Chemistry 24 (2022) 6556–6561; doi:10.1039/D2GC01932A

data_7245307
_publ_section_title
;
 Electrochemical oxidative regio- and stereo-selective
 thio(seleno)cyanation of enamides and mechanistic insights
;
_journal_issue                   17
_journal_name_full               'Green Chemistry'
_journal_page_first              6556
_journal_page_last               6561
_journal_paper_doi               10.1039/D2GC01932A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C17 H11 Br N2 O S'
_chemical_formula_sum            'C17 H11 Br N2 O S'
_chemical_formula_weight         371.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-20
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-04-20 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.269(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8390(12)
_cell_length_b                   9.1349(11)
_cell_length_c                   13.4055(16)
_cell_measurement_reflns_used    1939
_cell_measurement_temperature    249.97(10)
_cell_measurement_theta_max      25.0820
_cell_measurement_theta_min      2.6830
_cell_volume                     1551.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      249.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     44.00  98.00   1.00    5.00    --   12.05-178.00-180.00   54
  2  \w     35.00  86.00   1.00    5.00    --   12.05-178.00 -90.00   51
  3  \w    -28.00  63.00   1.00    5.00    --   12.05  19.00   0.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0127090000
_diffrn_orient_matrix_UB_12      -0.0424528000
_diffrn_orient_matrix_UB_13      -0.0406478000
_diffrn_orient_matrix_UB_21      0.0275405000
_diffrn_orient_matrix_UB_22      -0.0504832000
_diffrn_orient_matrix_UB_23      0.0348813000
_diffrn_orient_matrix_UB_31      -0.0470678000
_diffrn_orient_matrix_UB_32      -0.0410579000
_diffrn_orient_matrix_UB_33      -0.0008943000
_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  0.0524
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6587
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.398
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.786
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.0031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0540P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1853
_reflns_number_total             2726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc01932a2.cif
_cod_data_source_block           exp_3880
_cod_depositor_comments          'Adding full bibliography for 7245307.cif.'
_cod_database_code               7245307
_shelx_shelxl_version_number     2017/1
_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:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17)
;
_shelx_res_checksum              3706
_olex2_date_sample_data_collection 2022-04-20
_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 6.399
_oxdiff_exptl_absorpt_empirical_full_min 0.420