K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-mediated regio- and stereo-selective thiocyanation of enamides with NH<sub>4</sub>SCN.
Gu, Qingyun; Wang, Qiyang; Dai, Wenjing; Wang, Xin; Ban, Yingguo; Liu, Tianqing; Zhao, Yu; Zhang, Yanan; Ling, Yong; Zeng, Xiaobao; Organic & biomolecular chemistry 19 (2021) 2512–2516; doi:10.1039/d1ob00156f

data_7157907
_publ_section_title
;
 K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-mediated regio- and
 stereo-selective thiocyanation of enamides with NH<sub>4</sub>SCN.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2512
_journal_page_last               2516
_journal_paper_doi               10.1039/d1ob00156f
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C18 H15 Br N2 O S'
_chemical_formula_sum            'C18 H15 Br N2 O S'
_chemical_formula_weight         387.29
_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             2020-07-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2020-07-08 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.505(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6922(6)
_cell_length_b                   8.9341(8)
_cell_length_c                   17.5905(13)
_cell_measurement_reflns_used    3172
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      28.9370
_cell_measurement_theta_min      2.5870
_cell_volume                     1661.9(2)
_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 1.3 (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      99.9(4)
_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    -20.00  18.00   1.00    5.00    --  -11.59 -99.00 120.00   38
  2  \w     41.00  93.00   1.00    5.00    --   11.74-178.00 120.00   52
  3  \w    -26.00  90.00   1.00    5.00    --   11.74  19.00   0.00  116
;
_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      0.0198260000
_diffrn_orient_matrix_UB_12      -0.0196984000
_diffrn_orient_matrix_UB_13      0.0389895000
_diffrn_orient_matrix_UB_21      0.0243594000
_diffrn_orient_matrix_UB_22      -0.0686960000
_diffrn_orient_matrix_UB_23      -0.0118360000
_diffrn_orient_matrix_UB_31      0.0593085000
_diffrn_orient_matrix_UB_32      0.0345145000
_diffrn_orient_matrix_UB_33      -0.0013286000
_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  0.0508
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7414
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.926
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.604
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49684
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.042
_refine_diff_density_min         -1.611
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0508P)^2^+0.9953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2368
_reflns_number_total             2931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00156f2.cif
_cod_data_source_block           zxb-1_2
_cod_depositor_comments          'Adding full bibliography for 7157907.cif.'
_cod_database_code               7157907
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.94
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
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), C18(H18)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              94448
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.383
_oxdiff_exptl_absorpt_empirical_full_min 0.649