Transition-metal-free [3 + 2] cycloaddition of C,N-cycloazomethylimines with in situ formed isocyanates from dioxazolones: a facile synthesis of triazolinones
Chen, Lei; Yang, Peiyao; Wang, Qiuying; Zhao, Zhongxiang; Cui, Hui; Zhu, Liping; Green Chemistry 26 (2024) 3522–3526; doi:10.1039/D3GC04556K

data_7248100
_publ_section_title
;
 Transition-metal-free [3 + 2] cycloaddition of C,N-cycloazomethylimines
 with in situ formed isocyanates from dioxazolones: a facile synthesis of
 triazolinones
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              3522
_journal_page_last               3526
_journal_paper_doi               10.1039/D3GC04556K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C24 H20 F N3 O2'
_chemical_formula_sum            'C24 H20 F N3 O2'
_chemical_formula_weight         401.43
_chemical_name_systematic
3-benzoyl-1-(4-fluorophenyl)-9-methyl-1,5,6,10b-tetrahydro-[1,2,4]triazolo[5,1-a]isoquinolin-2(3H)-one
_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             2022-03-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-11-19 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.419(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5606(2)
_cell_length_b                   22.0542(4)
_cell_length_c                   9.7194(2)
_cell_measurement_reflns_used    8871
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7380
_cell_measurement_theta_min      3.9760
_cell_volume                     1944.36(7)
_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      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.954
_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     32.00  61.00   0.50    0.10    --   45.78  41.00 -62.00   58
  2  \w     65.00 106.00   0.50    0.10    --   45.78  41.00 -62.00   82
  3  \w    103.00 129.00   0.50    0.40    --  105.53  41.00 -62.00   52
  4  \w    152.00 177.00   0.50    0.40    --  105.53  41.00 -62.00   50
  5  \w     96.00 177.00   0.50    0.40    --  105.53  30.00  30.00  162
  6  \w      1.00  45.00   0.50    0.10    --   45.78 -41.00 144.00   88
  7  \w     32.00  64.00   0.50    0.40    --  105.53 -61.00 150.00   64
  8  \w     32.00  73.00   0.50    0.40    --  105.53 -61.00  90.00   82
  9  \w    -26.00   0.00   0.50    0.10    --   45.78 -41.00 144.00   52
 10  \w     33.00  72.00   0.50    0.40    --  105.53 -61.00  30.00   78
 11  \w     38.00  67.00   0.50    0.40    --  105.53 -61.00   0.00   58
 12  \w     66.00 107.00   0.50    0.40    --  105.53 -77.00-120.00   82
 13  \w     33.00  71.00   0.50    0.40    --  105.53 -61.00-150.00   76
 14  \w    -42.00  28.00   0.50    0.10    --  -45.78  41.00 -62.00  140
 15  \w    -60.00 -30.00   0.50    0.40    -- -100.00  61.00-120.00   60
 16  \w    -69.00 -34.00   0.50    0.40    -- -100.00  61.00 -60.00   70
 17  \w    -93.00 -14.00   0.50    0.10    --  -45.78 125.00  30.00  158
 18  \w     36.00  94.00   0.50    0.40    --  105.53 -94.00   0.00  116
 19  \w    -67.00 -27.00   0.50    0.40    -- -100.00  61.00 120.00   80
 20  \w   -122.00 -95.00   0.50    0.40    -- -100.00 -30.00  60.00   54
 21  \w    -84.00 -58.00   0.50    0.10    --  -45.78 -41.00 144.00   52
 22  \w   -173.00 -86.00   0.50    0.40    -- -100.00 -41.00 144.00  174
 23  \w   -172.00-147.00   0.50    0.40    -- -100.00 -30.00  60.00   50
 24  \w   -166.00-100.00   0.50    0.40    -- -100.00 -94.00-120.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0179255000
_diffrn_orient_matrix_UB_12      -0.0271833000
_diffrn_orient_matrix_UB_13      0.1395078000
_diffrn_orient_matrix_UB_21      -0.1540775000
_diffrn_orient_matrix_UB_22      -0.0237424000
_diffrn_orient_matrix_UB_23      -0.0873351000
_diffrn_orient_matrix_UB_31      0.0691297000
_diffrn_orient_matrix_UB_32      -0.0598022000
_diffrn_orient_matrix_UB_33      -0.0287806000
_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  0.0404
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13017
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.860
_diffrn_reflns_theta_min         4.009
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50028
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0022(3)
_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   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0602P)^2^+0.4290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1118
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3372
_reflns_number_total             3860
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc04556k2.cif
_cod_data_source_block           songnz_220307_2_auto
_cod_depositor_comments          'Adding full bibliography for 7248100.cif.'
_cod_database_code               7248100
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_shelx_estimated_absorpt_t_max   0.892
_shelx_estimated_absorpt_t_min   0.829
_reflns_odcompleteness_completeness 99.97
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00L(H00C,H00F), C00O(H00G,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00D(H00D), C00I(H00I), C00J(H00J),
 C00M(H00M), C00N(H00N), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T)
2.d Idealised Me refined as rotating group:
 C00U(H00K,H00L,H00O)
;
_shelx_res_checksum              94169
_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 1.840
_oxdiff_exptl_absorpt_empirical_full_min 0.399