A simple Iodine-DMSO-promoted multicomponent reaction for the synthesis of 2,4-disubstituted dihydrotriazole-3-ones
Liao, Hui; Huang, Zesheng; Zhu, Qiuhua; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00352J

data_7158633
_publ_section_title
;
 A simple Iodine-DMSO-promoted multicomponent reaction for the synthesis
 of 2,4-disubstituted dihydrotriazole-3-ones
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00352J
_journal_year                    2022
_chemical_formula_moiety         'C14 H11 N3 O'
_chemical_formula_sum            'C14 H11 N3 O'
_chemical_formula_weight         237.26
_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             2019-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-16 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.628(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7128(11)
_cell_length_b                   7.4784(7)
_cell_length_c                   11.7095(9)
_cell_measurement_reflns_used    1056
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.8020
_cell_measurement_theta_min      3.8160
_cell_volume                     1192.78(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1281
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_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 -17.00   1.00    1.00    --  -33.50 -57.00  90.00   28
  2  \w    -28.00  52.00   1.00    1.00    --   36.12 -37.00   0.00   80
  3  \w     54.00  81.00   1.00    1.00    --   36.12  57.00-120.00   27
  4  \w     19.00  46.00   1.00    1.00    --   36.12  57.00-120.00   27
  5  \w     60.00 107.00   1.00    1.00    --   36.12  19.00 120.00   47
  6  \w     -4.00  75.00   1.00    1.00    --   36.12 -99.00 -30.00   79
  7  \w      9.00  61.00   1.00    1.00    --   36.12  77.00 150.00   52
  8  \w    123.00 150.00   1.00    1.00    --  108.00 178.00 -90.00   27
  9  \w     60.00  95.00   1.00    1.00    --  108.00 178.00 -90.00   35
 10  \w     93.00 176.00   1.00    1.00    --  108.00  45.00-150.00   83
 11  \w     39.00  67.00   1.00    1.00    --  108.00 -94.00  60.00   28
 12  \w     84.00 109.00   1.00    1.00    --  108.00 -94.00  60.00   25
 13  \w     41.00 129.00   1.00    1.00    --  108.00-141.00 -18.00   88
 14  \w     92.00 131.00   1.00    1.00    --  108.00  61.00-180.00   39
 15  \w     81.00 174.00   1.00    1.00    --  108.00  77.00-120.00   93
 16  \w     40.00 135.00   1.00    1.00    --  108.00 -77.00 120.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0197994000
_diffrn_orient_matrix_UB_12      0.2025954000
_diffrn_orient_matrix_UB_13      0.0080155000
_diffrn_orient_matrix_UB_21      -0.0987437000
_diffrn_orient_matrix_UB_22      0.0359821000
_diffrn_orient_matrix_UB_23      -0.0732440000
_diffrn_orient_matrix_UB_31      -0.0514803000
_diffrn_orient_matrix_UB_32      0.0089769000
_diffrn_orient_matrix_UB_33      0.1100830000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4303
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.384
_diffrn_reflns_theta_min         3.245
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0106(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0408P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1447
_reflns_number_total             2258
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00352j2.cif
_cod_data_source_block           exp_10674
_cod_database_code               7158633
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.83
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_shelx_res_checksum              73147
_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 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.806