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_7244465
_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         'C15 H10 N2 O S'
_chemical_formula_sum            'C15 H10 N2 O S'
_chemical_formula_weight         266.31
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-30 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                86.836(3)
_cell_angle_beta                 77.121(4)
_cell_angle_gamma                71.464(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0053(3)
_cell_length_b                   8.4517(3)
_cell_length_c                   11.6853(6)
_cell_measurement_reflns_used    8215
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      76.6260
_cell_measurement_theta_min      3.8460
_cell_volume                     639.36(5)
_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(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.945
_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    113.00 177.00   0.50    0.10    --  104.80 125.00 150.00  128
  2  \w     79.00 167.00   0.50    0.10    --  104.80 148.00 136.00  176
  3  \w     96.00 177.00   0.50    0.10    --  104.80 123.00 -26.00  162
  4  \w    131.00 177.00   0.50    0.10    --  104.80  37.00-150.00   92
  5  \w     33.00 106.00   0.50    0.10    --  104.80 -99.00   0.00  146
  6  \w     47.00 108.00   0.50    0.05    --   49.51-148.00  89.00  122
  7  \w     47.00 128.00   0.50    0.10    --  104.80-148.00  89.00  162
  8  \w     33.00 106.00   0.50    0.10    --  104.80 -99.00 120.00  146
  9  \w     33.00 106.00   0.50    0.10    --  104.80 -99.00 -60.00  146
 10  \w     33.00 110.00   0.50    0.10    --  104.80-123.00-106.00  154
 11  \w     33.00 106.00   0.50    0.10    --  104.80 -99.00 -90.00  146
 12  \w     35.00 111.00   0.50    0.10    --  104.80-125.00-150.00  152
 13  \w     33.00  93.00   0.50    0.05    --   49.51-123.00-106.00  120
 14  \w     33.00 106.00   0.50    0.10    --  104.80 -99.00  90.00  146
 15  \w     33.00  66.00   0.50    0.10    --  104.80 -57.00 120.00   66
 16  \w     33.00  66.00   0.50    0.10    --  104.80 -57.00  90.00   66
 17  \w     33.00  66.00   0.50    0.10    --  104.80 -57.00 -60.00   66
 18  \w     33.00  66.00   0.50    0.10    --  104.80 -57.00 -90.00   66
 19  \w    -26.00  22.00   0.50    0.05    --  -49.51  19.00-120.00   96
 20  \w    -98.00 -43.00   0.50    0.05    --  -49.51   0.00-150.00  110
 21  \w    -26.00  22.00   0.50    0.05    --  -49.51  19.00 -90.00   96
 22  \w    -26.00  22.00   0.50    0.05    --  -49.51  19.00   0.00   96
 23  \w    -84.00 -11.00   0.50    0.05    --  -49.51 123.00 -26.00  146
 24  \w    -66.00 -18.00   0.50    0.10    --  -90.00  57.00 -30.00   96
 25  \w   -102.00 -25.00   0.50    0.05    --  -49.51 148.00 136.00  154
 26  \w   -102.00 -25.00   0.50    0.10    --  -90.00 148.00 136.00  154
 27  \w    -66.00 -18.00   0.50    0.10    --  -90.00  57.00  90.00   96
 28  \w   -138.00 -83.00   0.50    0.10    --  -90.00   0.00  90.00  110
 29  \w   -121.00 -45.00   0.50    0.05    --  -49.51 -19.00 -60.00  152
 30  \w   -161.00-134.00   0.50    0.10    --  -90.00 -77.00-150.00   54
 31  \w   -161.00-134.00   0.50    0.10    --  -90.00 -77.00 -90.00   54
 32  \w   -161.00-131.00   0.50    0.10    --  -90.00 -37.00 -90.00   60
 33  \w   -161.00-131.00   0.50    0.10    --  -90.00 -37.00 -60.00   60
 34  \w   -121.00 -45.00   0.50    0.05    --  -49.51 -19.00-180.00  152
 35  \w   -161.00-131.00   0.50    0.10    --  -90.00 -37.00   0.00   60
 36  \w   -161.00-131.00   0.50    0.10    --  -90.00 -37.00  30.00   60
 37  \w   -161.00-134.00   0.50    0.10    --  -90.00 -77.00  30.00   54
 38  \w   -161.00-126.00   0.50    0.10    --  -90.00 -99.00 -30.00   70
 39  \w   -161.00 -75.00   0.50    0.10    --  -90.00-123.00-106.00  172
 40  \w   -120.00 -57.00   0.50    0.05    --  -49.51-148.00  89.00  126
 41  \w   -151.00 -57.00   0.50    0.10    --  -90.00-148.00  89.00  188
 42  \w   -161.00-113.00   0.50    0.10    --  -90.00-125.00 120.00   96
 43  \w   -161.00-126.00   0.50    0.10    --  -90.00 -99.00 150.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2327709000
_diffrn_orient_matrix_UB_12      0.0449788000
_diffrn_orient_matrix_UB_13      0.0537025000
_diffrn_orient_matrix_UB_21      -0.0458607000
_diffrn_orient_matrix_UB_22      0.0321949000
_diffrn_orient_matrix_UB_23      -0.1236620000
_diffrn_orient_matrix_UB_31      0.0130191000
_diffrn_orient_matrix_UB_32      -0.1841516000
_diffrn_orient_matrix_UB_33      -0.0108970000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12094
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.463
_diffrn_reflns_theta_min         3.881
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.182
_exptl_crystal_colour            'clear orangish violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0588P)^2^+0.1012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2331
_reflns_number_total             2576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00049k2.cif
_cod_data_source_block           exp_229_auto
_cod_database_code               7244465
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHON
_shelx_estimated_absorpt_t_max   0.805
_shelx_estimated_absorpt_t_min   0.506
_diffrn_oxdiff_digest_frames
;
01c7c045c5f0dd209dab8b60ceef37c63e000626151
;
_diffrn_oxdiff_digest_hkl
;
01b03f2a82989fdee6a68829be65f0339c8042
;
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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), C8(H8), C17(H17), C9(H9), C13(H13), C15(H15), C16(H16), C14(H14)
;
_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 3.437
_oxdiff_exptl_absorpt_empirical_full_min 0.708