Synthesis of mesoionic triazolones <i>via</i> a formal [3+2] cycloaddition between 4-phenyl-1,2,4-triazoline-3,5-dione and alkynes.
Kuroda, Yusuke; Krell, Maya; Kurokawa, Kazuma; Takasu, Kiyosei; Chemical communications (Cambridge, England) 60 (2024) 1719–1722; doi:10.1039/d3cc05088b

data_7132651
_publ_section_title
;
 Synthesis of mesoionic triazolones <i>via</i> a formal [3+2]
 cycloaddition between 4-phenyl-1,2,4-triazoline-3,5-dione and alkynes.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1719
_journal_page_last               1722
_journal_paper_doi               10.1039/d3cc05088b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C17 H13 N3 O2'
_chemical_formula_sum            'C17 H14 N3 O2'
_chemical_formula_weight         292.31
_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             2021-10-19
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2023-09-04 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                102.103(3)
_cell_angle_beta                 109.324(3)
_cell_angle_gamma                102.128(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1044(2)
_cell_length_b                   10.0383(3)
_cell_length_c                   10.7169(3)
_cell_measurement_reflns_used    5931
_cell_measurement_temperature    100
_cell_measurement_theta_max      73.3780
_cell_measurement_theta_min      4.5860
_cell_volume                     672.07(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      100
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.961
_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     23.00  49.00   0.50    0.50    --    5.00  18.00-168.00   52
  2  \w     -8.00  19.00   0.50    0.50    --    5.00  18.00-168.00   54
  3  \w   -179.00-153.00   0.50    1.00    -- -100.90  18.00-168.00   52
  4  \w     17.00  93.00   0.50    0.50    --    5.00  55.00  60.00  152
  5  \w    -83.00  -7.00   0.50    0.50    --    5.00  55.00  60.00  152
  6  \w   -100.00 -57.00   0.50    0.50    --  -47.40  55.00 -30.00   86
  7  \w     10.00  41.00   0.50    0.50    --  -47.40  55.00-180.00   62
  8  \w    -15.00  41.00   0.50    0.50    --  -47.40  55.00 -30.00  112
  9  \w    -71.00 -25.00   0.50    0.50    --  -47.40  18.00-168.00   92
 10  \w     17.00  42.00   0.50    0.50    --  -47.40  55.00 -90.00   50
 11  \w      1.00  40.00   0.50    0.50    --  -47.40  55.00  30.00   78
 12  \w     13.00  41.00   0.50    0.50    --  -47.40  55.00-120.00   56
 13  \w    -42.00 -16.00   0.50    0.50    --  -52.00  55.00 111.48   52
 14  \w      7.00  36.00   0.50    0.50    --  -52.00  55.00 111.48   58
 15  \w     10.00  36.00   0.50    0.50    --  -52.00  55.00 141.16   52
 16  \w     -4.00  22.00   0.50    0.50    --  -64.00  54.00  46.61   52
 17  \w    -11.00  16.00   0.50    0.50    --  -64.00  52.00 138.88   54
 18  \w    -13.00  22.00   0.50    0.50    --  -64.00  53.00-151.67   70
 19  \w    -82.00 -56.00   0.50    0.50    --  -64.00  52.00 138.88   52
 20  \w      0.00  25.00   0.50    0.50    --  -64.00  55.00  89.26   50
 21  \w    -12.00  24.00   0.50    0.50    --  -64.00  55.00  -3.56   72
 22  \w    -15.00  21.00   0.50    0.50    --  -68.00  54.00 -92.90   72
 23  \w    -20.00  21.00   0.50    0.50    --  -68.00  55.00 121.79   82
 24  \w   -137.00-111.00   0.50    0.50    --  -68.00  55.00 121.79   52
 25  \w    -24.00  13.00   0.50    0.50    --  -72.00  55.00-166.80   74
 26  \w     -8.00  17.00   0.50    0.50    --  -72.00  55.00-125.75   50
 27  \w    -52.00 -26.00   0.50    0.50    --  -72.00  54.00 -46.81   52
 28  \w   -114.00 -58.00   0.50    0.50    --  -72.00  54.00 -46.81  112
 29  \w    -21.00  16.00   0.50    0.50    --  -72.00  54.00 -46.81   74
 30  \w   -159.00 -83.00   0.50    0.50    --  -72.00  55.00-125.75  152
 31  \w    -13.00  14.00   0.50    0.50    --  -72.00  54.00  84.50   54
 32  \w    -21.00  13.00   0.50    1.00    --  -76.00  55.00  42.33   68
 33  \w    -98.00 -27.00   0.50    1.00    --  -76.00  55.00  42.33  142
 34  \w    -15.00  11.00   0.50    1.00    --  -76.00  55.00  -5.62   52
 35  \w    -71.00 -26.00   0.50    1.00    -- -100.90  46.00-150.00   90
 36  \w   -182.00 -14.00   0.50    1.00    -- -100.90  52.00 115.88  336
 37  \w    -38.00 -12.00   0.50    1.00    -- -100.90  46.00 150.00   52
 38  \w   -139.00 -12.00   0.50    1.00    -- -100.90  46.00 -90.00  254
 39  \w   -173.00-147.00   0.50    1.00    -- -100.90  46.00 150.00   52
 40  \w    -65.00 -12.00   0.50    1.00    -- -100.90  54.00 -63.15  106
 41  \w   -185.00-160.00   0.50    1.00    -- -100.90  46.00 -90.00   50
 42  \w    -41.00 -16.00   0.50    1.00    -- -100.90  55.00 -23.61   50
 43  \w   -176.00-151.00   0.50    1.00    -- -100.90  55.00 -23.61   50
 44  \w    -77.00 -13.00   0.50    1.00    -- -100.90  37.00-120.00  128
 45  \w    -53.00 -17.00   0.50    1.00    -- -100.90  55.00  93.15   72
 46  \w   -167.00 -84.00   0.50    1.00    -- -100.90  55.00  93.15  166
 47  \w   -186.00-134.00   0.50    1.00    -- -100.90  54.00 -63.15  104
 48  \w   -166.00-140.00   0.50    1.00    -- -100.90  46.00   0.00   52
 49  \w    -54.00 -14.00   0.50    1.00    -- -100.90  54.00  26.80   80
 50  \w    -36.00 -11.00   0.50    1.00    -- -100.90  53.00-117.24   50
 51  \w    -75.00 -12.00   0.50    1.00    -- -100.90  46.00-180.00  126
 52  \w    -55.00 -14.00   0.50    1.00    -- -100.90  53.00-135.62   82
 53  \w   -181.00-155.00   0.50    1.00    -- -100.90  53.00-117.24   52
 54  \w    -37.00 -12.00   0.50    1.00    -- -100.90  46.00  60.00   50
 55  \w    -91.00 -43.00   0.50    1.00    -- -100.90  46.00  60.00   96
 56  \w   -117.00 -20.00   0.50    1.00    -- -100.90  28.00 150.00  194
 57  \w   -188.00 -70.00   0.50    1.00    -- -100.90  53.00-135.62  236
 58  \w    -38.00 -12.00   0.50    1.00    -- -100.90  46.00 120.00   52
 59  \w   -156.00 -11.00   0.50    1.00    -- -100.90  55.00 -15.13  290
 60  \w   -153.00 -19.00   0.50    1.00    -- -100.90  55.00  49.56  268
 61  \w    -89.00 -64.00   0.50    1.00    -- -100.90  46.00 120.00   50
 62  \w    -65.00 -13.00   0.50    1.00    -- -100.90  37.00 -60.00  104
 63  \w   -121.00 -69.00   0.50    1.00    -- -100.90  37.00 -60.00  104
 64  \w   -181.00-156.00   0.50    1.00    -- -100.90  55.00  49.56   50
 65  \w   -102.00 -12.00   0.50    1.00    -- -100.90  46.00   0.00  180
 66  \w   -134.00 -81.00   0.50    1.00    -- -100.90  18.00-168.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2143325000
_diffrn_orient_matrix_UB_12      -0.0471414000
_diffrn_orient_matrix_UB_13      0.0095240000
_diffrn_orient_matrix_UB_21      -0.0079779000
_diffrn_orient_matrix_UB_22      -0.1576878000
_diffrn_orient_matrix_UB_23      -0.0475207000
_diffrn_orient_matrix_UB_31      0.1101636000
_diffrn_orient_matrix_UB_32      0.0060486000
_diffrn_orient_matrix_UB_33      0.1523012000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13502
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.690
_diffrn_reflns_theta_min         4.587
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.444
_exptl_crystal_description       prism
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0550P)^2^+0.2280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2402
_reflns_number_total             2613
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05088b2.cif
_cod_data_source_block           kuroda211013
_cod_depositor_comments          'Adding full bibliography for 7132651.cif.'
_cod_database_code               7132651
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     -173
_reflns_odcompleteness_completeness 98.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L)
2.b Idealised Me refined as rotating group:
 C00M(H00A,H00B,H00M)
;
_shelx_res_checksum              44448
_shelx_hkl_checksum              28857
_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 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.816