Iodine-DMSO mediated conversion of N-arylcyanothioformamides to N-arylcyanoformamides and the unexpected formation of 2-cyanobenzothiazoles
Moussa, Ziad; Judeh, Zaher M. A.; Alzamly, Ahmed; Ahmed, Saleh A.; Tomah Al-Masri, Harbi; Al-Hindawi, Bassam; Rasool, Faisal; Saada, Sara; RSC Advances 12 (2022) 6133–6148; doi:10.1039/D2RA00049K

data_7244462
_publ_section_title
;
 Iodine-DMSO mediated conversion of N-arylcyanothioformamides to
 N-arylcyanoformamides and the unexpected formation of
 2-cyanobenzothiazoles
;
_journal_issue                   10
_journal_name_full               'RSC Advances'
_journal_page_first              6133
_journal_page_last               6148
_journal_paper_doi               10.1039/D2RA00049K
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C8 H5 Br N2 O'
_chemical_formula_sum            'C8 H5 Br N2 O'
_chemical_formula_weight         225.05
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-20 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                82.229(2)
_cell_angle_beta                 85.282(2)
_cell_angle_gamma                79.1919(19)
_cell_formula_units_Z            4
_cell_length_a                   8.65259(19)
_cell_length_b                   9.7551(2)
_cell_length_c                   10.0315(3)
_cell_measurement_reflns_used    7063
_cell_measurement_temperature    297.00(10)
_cell_measurement_theta_max      76.7990
_cell_measurement_theta_min      4.4720
_cell_volume                     822.66(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.939
_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     45.00 122.00   0.50    0.05    --   49.76  19.00 -30.00  154
  2  \w     45.00 122.00   0.50    0.05    --   49.76  19.00 -60.00  154
  3  \w     45.00 122.00   0.50    0.05    --   49.76  19.00 -90.00  154
  4  \w     45.00 122.00   0.50    0.05    --   49.76  19.00-150.00  154
  5  \w     45.00 122.00   0.50    0.05    --   49.76  19.00  60.00  154
  6  \w      1.00  56.00   0.50    0.05    --   49.76   0.00  90.00  110
  7  \w     36.00 121.00   0.50    0.05    --   49.76  64.00  87.00  170
  8  \w    -64.00  22.00   0.50    0.05    --  -49.76  64.00  87.00  172
  9  \w    -76.00 -18.00   0.50    0.17    --  -90.00  64.00  87.00  116
 10  \w    -26.00  22.00   0.50    0.05    --  -49.76  19.00   0.00   96
 11  \w    -66.00 -18.00   0.50    0.17    --  -90.00  57.00 -90.00   96
 12  \w    -66.00 -18.00   0.50    0.17    --  -90.00  57.00-120.00   96
 13  \w     56.00 111.00   0.50    0.17    --  104.80   0.00 120.00  110
 14  \w    131.00 177.00   0.50    0.17    --  104.80  37.00 120.00   92
 15  \w     91.00 177.00   0.50    0.17    --  104.80  64.00  87.00  172
 16  \w    131.00 177.00   0.50    0.17    --  104.80  37.00-180.00   92
 17  \w     56.00 111.00   0.50    0.17    --  104.80   0.00 -60.00  110
 18  \w    131.00 177.00   0.50    0.17    --  104.80  37.00 -30.00   92
 19  \w    137.00 177.00   0.50    0.17    --  104.80  57.00 -60.00   80
 20  \w    113.00 177.00   0.50    0.17    --  104.80 125.00  30.00  128
 21  \w     33.00  66.00   0.50    0.17    --  104.80 -57.00  30.00   66
 22  \w     33.00  76.00   0.50    0.17    --  104.80 -64.00 -48.00   86
 23  \w    -21.00  64.00   0.50    0.05    --   49.76 -64.00 -48.00  170
 24  \w     33.00  66.00   0.50    0.17    --  104.80 -57.00  90.00   66
 25  \w     33.00  66.00   0.50    0.17    --  104.80 -57.00 150.00   66
 26  \w     33.00 106.00   0.50    0.17    --  104.80 -99.00 120.00  146
 27  \w     33.00 106.00   0.50    0.17    --  104.80 -99.00  60.00  146
 28  \w     33.00 106.00   0.50    0.17    --  104.80 -99.00   0.00  146
 29  \w     33.00 106.00   0.50    0.17    --  104.80 -99.00 -30.00  146
 30  \w     35.00 111.00   0.50    0.17    --  104.80-125.00 -60.00  152
 31  \w     33.00 106.00   0.50    0.17    --  104.80 -99.00-180.00  146
 32  \w     35.00  94.00   0.50    0.05    --   49.76-125.00-180.00  118
 33  \w   -120.00 -36.00   0.50    0.05    --  -49.76 -64.00 -48.00  168
 34  \w   -161.00-134.00   0.50    0.17    --  -90.00 -77.00 -90.00   54
 35  \w   -161.00-134.00   0.50    0.17    --  -90.00 -77.00 -60.00   54
 36  \w   -161.00-134.00   0.50    0.17    --  -90.00 -77.00   0.00   54
 37  \w   -161.00 -76.00   0.50    0.17    --  -90.00 -64.00 -48.00  170
 38  \w   -121.00 -45.00   0.50    0.05    --  -49.76 -19.00  60.00  152
 39  \w   -121.00 -45.00   0.50    0.05    --  -49.76 -21.00 141.26  152
 40  \w   -161.00-131.00   0.50    0.17    --  -90.00 -37.00  90.00   60
 41  \w   -161.00-126.00   0.50    0.17    --  -90.00 -99.00  90.00   70
 42  \w   -161.00-126.00   0.50    0.17    --  -90.00 -99.00-120.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1075989000
_diffrn_orient_matrix_UB_12      0.0832345000
_diffrn_orient_matrix_UB_13      -0.1093683000
_diffrn_orient_matrix_UB_21      -0.0453359000
_diffrn_orient_matrix_UB_22      -0.1377648000
_diffrn_orient_matrix_UB_23      -0.0296390000
_diffrn_orient_matrix_UB_31      -0.1390525000
_diffrn_orient_matrix_UB_32      0.0182962000
_diffrn_orient_matrix_UB_33      0.1061431000
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14176
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.459
_diffrn_reflns_theta_min         4.456
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.405
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
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    1.817
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0381P)^2^+0.3986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2977
_reflns_number_total             3283
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00049k2.cif
_cod_data_source_block           exp_218_auto
_cod_original_cell_volume        822.66(3)
_cod_database_code               7244462
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C32  H20  Br4  N8  O4  '
_shelx_estimated_absorpt_t_max   0.645
_shelx_estimated_absorpt_t_min   0.389
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C5(H5), C7(H7), C4(H4), C19(H19), C8(H8), C16(H16), C15(H15)
;
_shelx_res_checksum              15160
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   361
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.686
_oxdiff_exptl_absorpt_empirical_full_min 0.601