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_7244463
_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         'C10 H8 N2 O2 S'
_chemical_formula_sum            'C10 H8 N2 O2 S'
_chemical_formula_weight         220.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-28 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.509(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9979(2)
_cell_length_b                   15.5449(11)
_cell_length_c                   15.9729(8)
_cell_measurement_reflns_used    3863
_cell_measurement_temperature    297.00(10)
_cell_measurement_theta_max      76.6170
_cell_measurement_theta_min      5.4810
_cell_volume                     992.63(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (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 0.973
_diffrn_measured_fraction_theta_max 0.906
_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   -103.00 -25.00   0.50    1.39    --  -49.51 149.00  73.00  156
  2  \w    -84.00 -11.00   0.50    1.39    --  -49.51 123.00 -90.00  146
  3  \w   -120.00 -57.00   0.50    1.39    --  -49.51-149.00  26.00  126
  4  \w     47.00 109.00   0.50    1.39    --   49.51-149.00  26.00  124
  5  \w     33.00  93.00   0.50    1.39    --   49.51-123.00-170.00  120
  6  \w   -103.00 -25.00   0.50    5.54    --  -90.00 149.00  73.00  156
  7  \w   -161.00 -75.00   0.50    5.54    --  -90.00-123.00-170.00  172
  8  \w     33.00 110.00   0.50    5.54    --  104.80-123.00-170.00  154
  9  \w     47.00 129.00   0.50    5.54    --  104.80-149.00  26.00  164
 10  \w    122.00 158.00   0.50    5.54    --  104.80 149.00  73.00   72
 11  \w    -23.00  18.00   0.50    1.39    --  -49.51  19.00-150.00   82
 12  \w    -26.00  13.00   0.50    1.39    --  -49.51  19.00 120.00   78
 13  \w    -10.00  20.00   0.50    1.39    --  -49.51  19.00  60.00   60
 14  \w     -5.00  21.00   0.50    1.39    --   49.51 -19.00 120.00   52
 15  \w   -160.00-131.00   0.50    5.54    --  -90.00 -37.00-120.00   58
 16  \w   -160.00-131.00   0.50    5.54    --  -90.00 -37.00-180.00   58
 17  \w   -159.00-127.00   0.50    5.54    --  -90.00 -99.00 -30.00   64
 18  \w   -159.00-132.00   0.50    5.54    --  -90.00 -37.00 -90.00   54
 19  \w   -161.00-136.00   0.50    5.54    --  -90.00 -77.00  30.00   50
 20  \w   -160.00-133.00   0.50    5.54    --  -90.00 -37.00-150.00   54
 21  \w   -161.00-133.00   0.50    5.54    --  -90.00 -37.00 -60.00   56
 22  \w   -161.00-128.00   0.50    5.54    --  -90.00 -99.00 120.00   66
 23  \w     57.00 106.00   0.50    5.54    --  104.80 -99.00-120.00   98
 24  \w    115.00 175.00   0.50    5.54    --  104.80 125.00 -30.00  120
 25  \w     33.00  58.00   0.50    5.54    --  104.80 -57.00  60.00   50
 26  \w     38.00  63.00   0.50    5.54    --  104.80 -57.00 -30.00   50
 27  \w    137.00 162.00   0.50    5.54    --  104.80  57.00-180.00   50
 28  \w     38.00  63.00   0.50    5.54    --  104.80 -57.00 -90.00   50
 29  \w     37.00  65.00   0.50    5.54    --  104.80 -57.00-120.00   56
;
_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      0.0573435000
_diffrn_orient_matrix_UB_12      -0.0637842000
_diffrn_orient_matrix_UB_13      -0.0723861000
_diffrn_orient_matrix_UB_21      -0.0028702000
_diffrn_orient_matrix_UB_22      -0.0753605000
_diffrn_orient_matrix_UB_23      0.0625373000
_diffrn_orient_matrix_UB_31      -0.3810061000
_diffrn_orient_matrix_UB_32      -0.0090450000
_diffrn_orient_matrix_UB_33      -0.0121376000
_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  0.0609
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7605
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.364
_diffrn_reflns_theta_min         5.540
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.752
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0752P)^2^+0.1720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1491
_reflns_number_total             1900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00049k2.cif
_cod_data_source_block           exp_235_auto
_cod_database_code               7244463
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.515
_reflns_odcompleteness_completeness 97.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              72006
_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 3.558
_oxdiff_exptl_absorpt_empirical_full_min 0.531