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_7244466
_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 H9 I N2 O3'
_chemical_formula_sum            'C10 H9 I N2 O3'
_chemical_formula_weight         332.09
_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             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                90
_cell_angle_beta                 101.469(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7562(4)
_cell_length_b                   4.73210(10)
_cell_length_c                   16.9571(4)
_cell_measurement_reflns_used    7623
_cell_measurement_temperature    297.00(10)
_cell_measurement_theta_max      76.7000
_cell_measurement_theta_min      5.2720
_cell_volume                     1160.43(5)
_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 0.9992
_diffrn_measured_fraction_theta_max 0.9401
_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     45.00 111.00   0.50    0.12    --   49.76  19.00  90.00  132
  2  \w     44.00 121.00   0.50    0.12    --   49.76  38.00 138.00  154
  3  \w     99.00 176.00   0.50    0.46    --  104.80  38.00 138.00  154
  4  \w    137.00 177.00   0.50    0.46    --  104.80  57.00   0.00   80
  5  \w     33.00  66.00   0.50    0.46    --  104.80 -57.00-150.00   66
  6  \w     33.00  66.00   0.50    0.46    --  104.80 -57.00-180.00   66
  7  \w     33.00  66.00   0.50    0.46    --  104.80 -57.00-120.00   66
  8  \w    -21.00  43.00   0.50    0.12    --   49.76 -38.00 -16.00  128
  9  \w     33.00  66.00   0.50    0.46    --  104.80 -57.00   0.00   66
 10  \w     33.00  66.00   0.50    0.46    --  104.80 -57.00  30.00   66
 11  \w     33.00  66.00   0.50    0.46    --  104.80 -57.00  60.00   66
 12  \w     33.00  66.00   0.50    0.46    --  104.80 -57.00 150.00   66
 13  \w     33.00 106.00   0.50    0.46    --  104.80 -99.00 -90.00  146
 14  \w    -26.00  22.00   0.50    0.12    --  -49.76  19.00 -90.00   96
 15  \w    -43.00  21.00   0.50    0.12    --  -49.76  38.00 138.00  128
 16  \w    -98.00 -43.00   0.50    0.12    --  -49.76   0.00  90.00  110
 17  \w   -161.00-134.00   0.50    0.46    --  -90.00 -77.00 120.00   54
 18  \w   -161.00-134.00   0.50    0.46    --  -90.00 -77.00  30.00   54
 19  \w   -161.00-134.00   0.50    0.46    --  -90.00 -77.00   0.00   54
 20  \w   -161.00-134.00   0.50    0.46    --  -90.00 -77.00 -30.00   54
 21  \w   -161.00-134.00   0.50    0.46    --  -90.00 -77.00 -90.00   54
 22  \w   -161.00-131.00   0.50    0.46    --  -90.00 -37.00-150.00   60
 23  \w   -161.00-131.00   0.50    0.46    --  -90.00 -37.00-120.00   60
 24  \w   -161.00 -84.00   0.50    0.46    --  -90.00 -38.00 -16.00  154
 25  \w   -120.00 -44.00   0.50    0.12    --  -49.76 -38.00 -16.00  152
 26  \w   -161.00-131.00   0.50    0.46    --  -90.00 -37.00 -60.00   60
 27  \w   -161.00-131.00   0.50    0.46    --  -90.00 -37.00 -90.00   60
 28  \w   -121.00 -45.00   0.50    0.12    --  -49.76 -19.00-150.00  152
 29  \w   -161.00-126.00   0.50    0.46    --  -90.00 -99.00-180.00   70
 30  \w   -161.00-126.00   0.50    0.46    --  -90.00 -99.00 150.00   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      0.0282071000
_diffrn_orient_matrix_UB_12      0.0780245000
_diffrn_orient_matrix_UB_13      0.0897339000
_diffrn_orient_matrix_UB_21      -0.0955656000
_diffrn_orient_matrix_UB_22      0.1359362000
_diffrn_orient_matrix_UB_23      -0.0031641000
_diffrn_orient_matrix_UB_31      -0.0377563000
_diffrn_orient_matrix_UB_32      -0.2852677000
_diffrn_orient_matrix_UB_33      0.0230321000
_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  0.0338
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11384
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.660
_diffrn_reflns_theta_min         3.056
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    21.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0363P)^2^+1.1012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0761
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2079
_reflns_number_total             2300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00049k2.cif
_cod_data_source_block           exp_233_auto
_cod_database_code               7244466
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.671
_shelx_estimated_absorpt_t_min   0.221
_reflns_odcompleteness_completeness 99.92
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N8(H8), C6(H6), C3(H3)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_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 2.263
_oxdiff_exptl_absorpt_empirical_full_min 0.666