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_7133067
_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         'C15 H10 Br N S'
_chemical_formula_sum            'C15 H10 Br N S'
_chemical_formula_weight         316.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-11
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.4897(2)
_cell_length_b                   18.6819(4)
_cell_length_c                   19.2474(4)
_cell_measurement_reflns_used    6829
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.2890
_cell_measurement_theta_min      4.5900
_cell_volume                     2693.13(11)
_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 0.998
_diffrn_measured_fraction_theta_max 0.970
_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     36.00  64.00   0.50    0.88    --  106.05 -61.00 150.00   56
  2  \w     39.00  65.00   0.50    0.88    --  106.05 -61.00   0.00   52
  3  \w     35.00  60.00   0.50    0.88    --  106.05 -61.00-180.00   50
  4  \w     96.00 178.00   0.50    0.88    --  106.05  57.00-124.00  164
  5  \w     92.00 177.00   0.50    0.88    --  106.05  83.00  99.00  170
  6  \w    -30.00  -3.00   0.50    0.45    --   42.33 -19.00 150.00   54
  7  \w    -31.00  19.00   0.50    0.45    --   42.33 -19.00  30.00  100
  8  \w    -35.00  19.00   0.50    0.45    --   42.33 -19.00 -30.00  108
  9  \w    -28.00  -2.00   0.50    0.45    --   42.33 -19.00-180.00   52
 10  \w     -6.00  29.00   0.50    0.45    --  -42.33  83.00  99.00   70
 11  \w    -73.00 -36.00   0.50    0.88    -- -106.00  61.00  90.00   74
 12  \w    -70.00 -33.00   0.50    0.45    --  -42.33  83.00  99.00   74
 13  \w   -137.00 -61.00   0.50    0.88    -- -106.00  83.00  -9.00  152
 14  \w    -73.00 -37.00   0.50    0.88    -- -106.00  61.00 -60.00   72
;
_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      0.1362323000
_diffrn_orient_matrix_UB_12      0.0256573000
_diffrn_orient_matrix_UB_13      0.0546020000
_diffrn_orient_matrix_UB_21      -0.0361607000
_diffrn_orient_matrix_UB_22      -0.0676161000
_diffrn_orient_matrix_UB_23      0.0436703000
_diffrn_orient_matrix_UB_31      0.1498345000
_diffrn_orient_matrix_UB_32      -0.0395472000
_diffrn_orient_matrix_UB_33      -0.0390156000
_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  0.0383
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9183
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.416
_diffrn_reflns_theta_min         4.595
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.435
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.560
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.830
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0365
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2413
_reflns_number_total             2673
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01666a2.cif
_cod_data_source_block           exp_763_auto
_cod_depositor_comments
'Adding full bibliography for 7133066--7133067.cif.'
_cod_database_code               7133067
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H Br'
_chemical_oxdiff_usercomment     '150 K'
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.292
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C7(H7), C10(H10), C11(H11), C12(H12), C4(H4), C3(H3), C13(H13),
 C5(H5), C6(H6)
;
_shelx_res_checksum              5294
_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 2.324
_oxdiff_exptl_absorpt_empirical_full_min 0.491