Metal-catalyzed divergent synthesis from ylides with 3-arylbenzo[<i>d</i>][1,2,3]triazin-4(3<i>H</i>)-ones.
Bao, Mei-Zhu; Pan, Xiao-Ying; Wu, Wen-Rong; Xiao, Lin; Liu, Jidan; Liu, Xu-Ge; Zhang, Shang-Shi; Zhao, Limin; Chemical communications (Cambridge, England) 60 (2024) 12928–12931; doi:10.1039/d4cc04309j

data_7133855
_publ_section_title
;
 Metal-catalyzed divergent synthesis from ylides with
 3-arylbenzo[<i>d</i>][1,2,3]triazin-4(3<i>H</i>)-ones.
;
_journal_issue                   88
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12928
_journal_page_last               12931
_journal_paper_doi               10.1039/d4cc04309j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C H Cl3, C19 H17 N3 O3'
_chemical_formula_sum            'C20 H18 Cl3 N3 O3'
_chemical_formula_weight         454.72
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-24
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-08-13 deposited with the CCDC.	2024-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                70.151(3)
_cell_angle_beta                 89.702(3)
_cell_angle_gamma                85.415(3)
_cell_formula_units_Z            4
_cell_length_a                   10.2448(4)
_cell_length_b                   14.5349(5)
_cell_length_c                   14.7931(5)
_cell_measurement_reflns_used    6390
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.8370
_cell_measurement_theta_min      3.1340
_cell_volume                     2064.74(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_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    -62.00  31.00   1.00    1.00    --  -40.73  38.00 120.00   93
  2  \w    -65.00  32.00   1.00    1.00    --  -40.73  57.00 -30.00   97
  3  \w     46.00  80.00   1.00    1.00    --   40.73 -99.00  90.00   34
  4  \w     23.00  63.00   1.00    1.00    --   40.73-125.00  30.00   40
  5  \w     35.00  72.00   1.00    1.00    --  107.58 -61.00 150.00   37
  6  \w     33.00 108.00   1.00    1.00    --  107.58 -94.00 150.00   75
  7  \w     35.00 122.00   1.00    1.00    --  107.58-125.00 120.00   87
  8  \w     32.00 135.00   1.00    1.00    --  107.58 -77.00 -60.00  103
  9  \w     76.00 105.00   1.00    1.00    --  107.58 -94.00 -90.00   29
 10  \w     66.00 118.00   1.00    1.00    --  107.58 -30.00-120.00   52
 11  \w     82.00 178.00   1.00    1.00    --  107.58  45.00 -60.00   96
 12  \w    100.00 127.00   1.00    1.00    --  107.58 125.00 -30.00   27
 13  \w    104.00 152.00   1.00    1.00    --  107.58 125.00-120.00   48
 14  \w     78.00 177.00   1.00    1.00    --  107.58  61.00  30.00   99
 15  \w    119.00 166.00   1.00    1.00    --  107.58   0.00  90.00   47
 16  \w     55.00  84.00   1.00    1.00    --  107.58   0.00  90.00   29
 17  \w     46.00  73.00   1.00    1.00    --  107.58 -94.00 -90.00   27
 18  \w     26.00  98.00   1.00    1.00    --  107.58 -94.00-120.00   72
 19  \w   -109.00 -15.00   1.00    1.00    --  -40.73 -57.00-180.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0295529000
_diffrn_orient_matrix_UB_12      -0.0009671000
_diffrn_orient_matrix_UB_13      0.1025203000
_diffrn_orient_matrix_UB_21      -0.1264590000
_diffrn_orient_matrix_UB_22      0.0668557000
_diffrn_orient_matrix_UB_23      -0.0378988000
_diffrn_orient_matrix_UB_31      -0.0768471000
_diffrn_orient_matrix_UB_32      -0.0911900000
_diffrn_orient_matrix_UB_33      0.0178502000
_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  0.0411
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14771
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.763
_diffrn_reflns_theta_min         3.177
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.254
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.088
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         8122
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0929P)^2^+0.7245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6834
_reflns_number_total             8122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04309j2.cif
_cod_data_source_block           exp_5067
_cod_depositor_comments
'Adding full bibliography for 7133854--7133855.cif.'
_cod_database_code               7133855
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 C16, C17
 with sigma for 1-2 distances of 0.0008 and sigma for 1-3 distances of 0.0008
3. Uiso/Uaniso restraints and constraints
C17 \\sim C16: within 2A with sigma of 0.0006 and sigma for terminal atoms of
0.0012 within 2A
4.a Ternary CH refined with riding coordinates:
 C40(H40), C39(H39)
4.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C35(H35A,H35B), C36(H36A,
 H36B), C37(H37A,H37B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11),
 C12(H12), N4(H4A), N5(H5A), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
 C28(H28), C29(H29), C30(H30), C31(H31)
;
_shelx_res_checksum              2960
_shelx_hkl_checksum              12390
_olex2_date_sample_data_collection 2024-02-23
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.001
_oxdiff_exptl_absorpt_empirical_full_min 0.665