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_7244464
_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_absolute_configuration rm
_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      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7218(16)
_cell_length_b                   18.260(2)
_cell_length_c                   3.9580(7)
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    297.00(10)
_cell_measurement_theta_max      72.9700
_cell_measurement_theta_min      3.9770
_cell_volume                     991.7(2)
_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 2018/2 (Sheldrick, 2018)'
_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 0.9928
_diffrn_measured_fraction_theta_max 0.8194
_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    -57.00 -18.00   0.50   14.40    --  -90.00  50.00 148.00   78
  2  \w   -161.00 -81.00   0.50   14.40    --  -90.00-111.00 133.00  160
  3  \w   -161.00 -81.00   0.50   14.40    --  -90.00 -50.00   1.00  160
  4  \w     87.00 177.00   0.50   14.40    --  104.80  74.00 -17.00  180
  5  \w    -86.00 -35.00   0.50    3.60    --  -48.51 125.00 150.00  102
  6  \w    -86.00 -35.00   0.50    3.60    --  -48.51 125.00 -90.00  102
  7  \w    -26.00  23.00   0.50    3.60    --  -48.51  19.00  90.00   98
  8  \w    -23.00  26.00   0.50    3.60    --   48.51 -19.00 -60.00   98
  9  \w   -161.00-131.00   0.50   14.40    --  -90.00 -37.00 150.00   60
 10  \w   -161.00-131.00   0.50   14.40    --  -90.00 -37.00 120.00   60
 11  \w   -161.00-113.00   0.50   14.40    --  -90.00-125.00 120.00   96
 12  \w    131.00 177.00   0.50   14.40    --  104.80  37.00-150.00   92
 13  \w     33.00  66.00   0.50   14.40    --  104.80 -57.00-150.00   66
 14  \w   -120.00 -44.00   0.50    3.60    --  -48.51 -19.00 120.00  152
 15  \w     44.00  91.00   0.50    3.60    --   48.51  19.00 -60.00   94
;
_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      0.0196388000
_diffrn_orient_matrix_UB_12      -0.0823843000
_diffrn_orient_matrix_UB_13      -0.0493570000
_diffrn_orient_matrix_UB_21      0.0648837000
_diffrn_orient_matrix_UB_22      -0.0002363000
_diffrn_orient_matrix_UB_23      0.3174510000
_diffrn_orient_matrix_UB_31      -0.0894906000
_diffrn_orient_matrix_UB_32      -0.0181579000
_diffrn_orient_matrix_UB_33      0.2198233000
_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  0.0826
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            4966
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.921
_diffrn_reflns_theta_min         4.030
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52888
_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            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 395 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1696
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0704
_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^)+(0.1196P)^2^+0.6250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.2219
_reflns_Friedel_coverage         0.525
_reflns_Friedel_fraction_full    0.757
_reflns_Friedel_fraction_max     0.666
_reflns_number_gt                1298
_reflns_number_total             1696
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00049k2.cif
_cod_data_source_block           exp_240_auto
_cod_database_code               7244464
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.541
_diffrn_oxdiff_digest_frames
;
014985b5738fa606a317642c4979a6368900025107a
;
_diffrn_oxdiff_digest_hkl
;
011ac7e986689df2ecbf23b9215d7236cd10c4
;
_reflns_odcompleteness_completeness 99.28
_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), C2(H2)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C11(H11A,H11B,H11C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 3.196
_oxdiff_exptl_absorpt_empirical_full_min 0.231