Synthesis of <i>N</i>-β-brominated alkenyl isothiocyanates <i>via</i> dehydrogenation of alkyl isothiocyanates.
Maeda, Bumpei; Akiyoshi, Ryohei; Tanaka, Daisuke; Sato, Kohei; Murakami, Kei; Chemical communications (Cambridge, England) 60 (2024) 6015–6018; doi:10.1039/d4cc01666a

data_7133066
_publ_section_title
;
 Synthesis of <i>N</i>-&#x3b2;-brominated alkenyl isothiocyanates
 <i>via</i> dehydrogenation of alkyl isothiocyanates.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6015
_journal_page_last               6018
_journal_paper_doi               10.1039/d4cc01666a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C13 H8 Br N S'
_chemical_formula_sum            'C13 H8 Br N S'
_chemical_formula_weight         290.17
_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             2023-10-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-27 deposited with the CCDC.	2024-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.820(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7154(2)
_cell_length_b                   14.3463(3)
_cell_length_c                   7.00360(10)
_cell_measurement_reflns_used    5302
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.6190
_cell_measurement_theta_min      3.8620
_cell_volume                     1147.77(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_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    -62.00 -36.00   0.50    0.91    -- -106.00 135.00   4.00   52
  2  \w   -118.00 -72.00   0.50    0.91    -- -106.00 135.00   4.00   92
  3  \w   -112.00 -81.00   0.50    0.91    -- -106.00 125.00 -90.00   62
  4  \w   -116.00 -79.00   0.50    0.91    -- -106.00 134.00-174.00   74
  5  \w    -67.00 -35.00   0.50    0.45    --  -42.33 134.00-174.00   64
  6  \w    -65.00 -40.00   0.50    0.91    -- -106.00   0.00 -60.00   50
  7  \w    -71.00 -37.00   0.50    0.91    -- -106.00  61.00-120.00   68
  8  \w    -67.00 -38.00   0.50    0.91    -- -106.00  61.00-150.00   58
  9  \w    -67.00 -37.00   0.50    0.91    -- -106.00   0.00 -90.00   60
 10  \w    -39.00  34.00   0.50    0.45    --  -42.33  37.00 -30.00  146
 11  \w    -17.00  36.00   0.50    0.45    --  -42.33  19.00  90.00  106
 12  \w    -69.00 -32.00   0.50    0.91    -- -106.00  61.00 150.00   74
 13  \w    -67.00 -33.00   0.50    0.91    -- -106.00  61.00  60.00   68
 14  \w    -65.00 -36.00   0.50    0.91    -- -106.00   0.00-120.00   58
 15  \w    -67.00 -35.00   0.50    0.91    -- -106.00   0.00-180.00   64
 16  \w    -67.00 -42.00   0.50    0.91    -- -106.00   0.00-150.00   50
 17  \w   -147.00-122.00   0.50    0.91    -- -106.00-134.00 117.00   50
 18  \w     37.00  97.00   0.50    0.45    --   42.33-134.00 117.00  120
 19  \w     52.00  77.00   0.50    0.91    --  106.05-134.00 117.00   50
 20  \w     33.00  61.00   0.50    0.91    --  106.05 -94.00 120.00   56
 21  \w     52.00  78.00   0.50    0.91    --  106.05 -94.00 150.00   52
 22  \w     76.00 103.00   0.50    0.91    --  106.05 -94.00 120.00   54
 23  \w     33.00  70.00   0.50    0.91    --  106.05 -61.00 -60.00   74
 24  \w    -37.00  19.00   0.50    0.45    --   42.33 -19.00 -90.00  112
 25  \w     76.00 102.00   0.50    0.45    --   42.33 135.00   4.00   52
 26  \w     68.00 126.00   0.50    0.91    --  106.05 135.00   4.00  116
 27  \w     67.00  92.00   0.50    0.45    --   42.33 134.00-174.00   50
 28  \w     74.00  99.00   0.50    0.91    --  106.05 134.00-174.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0636967000
_diffrn_orient_matrix_UB_12      0.0943801000
_diffrn_orient_matrix_UB_13      0.0383484000
_diffrn_orient_matrix_UB_21      0.1176250000
_diffrn_orient_matrix_UB_22      -0.0512296000
_diffrn_orient_matrix_UB_23      0.0675039000
_diffrn_orient_matrix_UB_31      0.0171884000
_diffrn_orient_matrix_UB_32      0.0007314000
_diffrn_orient_matrix_UB_33      -0.2117806000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6034
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.025
_diffrn_reflns_theta_max         67.025
_diffrn_reflns_theta_min         3.870
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.314
_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 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.679
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0737P)^2^+0.0412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.0999
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1903
_reflns_number_total             2037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01666a2.cif
_cod_data_source_block           murakamilab_hex_autored
_cod_depositor_comments
'Adding full bibliography for 7133066--7133067.cif.'
_cod_database_code               7133066
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S N Br'
_chemical_oxdiff_usercomment     '150 K'
_shelx_estimated_absorpt_t_max   0.743
_shelx_estimated_absorpt_t_min   0.144
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C2(H2), C8(H8), C6(H6), C12(H12), C3(H3)
;
_shelx_res_checksum              76627
_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 1.711
_oxdiff_exptl_absorpt_empirical_full_min 0.519