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_7133854
_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         'C22 H21 N3 O3'
_chemical_formula_sum            'C22 H21 N3 O3'
_chemical_formula_weight         375.42
_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             2023-10-13
_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                90
_cell_angle_beta                 92.354(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6241(2)
_cell_length_b                   20.0539(4)
_cell_length_c                   18.4446(4)
_cell_measurement_reflns_used    7375
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.4880
_cell_measurement_theta_min      3.1830
_cell_volume                     3926.39(14)
_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      149.99(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 0.973
_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     20.00  52.00   1.00    1.00    --   40.73 -38.00 120.00   32
  2  \w     34.00  60.00   1.00    1.00    --   40.73-129.00  75.00   26
  3  \w     29.00  95.00   1.00    1.00    --   40.73-125.00 -30.00   66
  4  \w     44.00 131.00   1.00    1.20    --  107.58 -45.00 -30.00   87
  5  \w     80.00 177.00   1.00    1.20    --  107.58  30.00 150.00   97
  6  \w     94.00 122.00   1.00    1.20    --  107.58 125.00 150.00   28
  7  \w     96.00 122.00   1.00    1.20    --  107.58 125.00 -30.00   26
  8  \w     36.00 107.00   1.00    1.20    --  107.58 -94.00 -30.00   71
  9  \w     34.00 120.00   1.00    1.20    --  107.58-125.00 -90.00   86
 10  \w     35.00  91.00   1.00    1.20    --  107.58 -94.00 -90.00   56
 11  \w    -78.00  36.00   1.00    1.00    --  -40.73   0.00  60.00  114
;
_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      -0.1137285000
_diffrn_orient_matrix_UB_12      -0.0286566000
_diffrn_orient_matrix_UB_13      0.0388579000
_diffrn_orient_matrix_UB_21      -0.0494402000
_diffrn_orient_matrix_UB_22      0.0711493000
_diffrn_orient_matrix_UB_23      0.0123278000
_diffrn_orient_matrix_UB_31      -0.0755843000
_diffrn_orient_matrix_UB_32      -0.0033149000
_diffrn_orient_matrix_UB_33      -0.0729677000
_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  0.0419
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15823
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.675
_diffrn_reflns_theta_min         3.257
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53419
_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            'light colourless'
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         7720
_refine_ls_number_restraints     419
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0746
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0999P)^2^+3.6189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1969
_refine_ls_wR_factor_ref         0.2093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6331
_reflns_number_total             7720
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04309j2.cif
_cod_data_source_block           xl-01
_cod_depositor_comments
'Adding full bibliography for 7133854--7133855.cif.'
_cod_database_code               7133854
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N6-N5 \\sim N6-N00F
 with sigma of 0.02
 N6-C29 \\sim N6-C45
 with sigma of 0.02
 O4-C29 \\sim OA-C45
 with sigma of 0.02
 C28-C29 \\sim C00{-C45
 with sigma of 0.02
 C28-C27 \\sim C00{-C01L
 with sigma of 0.02
 C25-C26 \\sim C0-C48
 with sigma of 0.02
 C28-C26 \\sim C00{-C48
 with sigma of 0.04
 C25-C27 \\sim C0-C01L
 with sigma of 0.04
 C26-C27 \\sim C48-C01L
 with sigma of 0.02
 C29-C27 \\sim C45-C01L
 with sigma of 0.04
 N6-O4 \\sim N6-OA
 with sigma of 0.04
 N6-C28 \\sim N6-C00{
 with sigma of 0.04
 O4-C28 \\sim OA-C00{
 with sigma of 0.04
3. Rigid bond restraints
 C6, N1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C6 \\sim N1: within 2A with sigma of 0.0006 and sigma for terminal atoms of
0.0012 within 2A
5. Rigid body (RIGU) restrains
 O4, O5, H5, O6, OA, N00F, N4, N5, N6, N7, C0, H0, C00{, C01L, H01L, C23, C24,
 H24, C25, H25, C26, H26, C27, H27, C28, C29, C30, C31, H31, C32, C33, H33, C34,
  H34, C35, C36, C37, H37A, H37B, H37C, C38, C39, H39A, H39B, C40, C41, H41A,
 H41B, C42, C43, H43A, H43B, H43C, C44, H44A, H44B, H44C, C45, C46, C47, H47,
 C48, H48
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.004
 N1, N2, N3, C7, C1, C6, C2, C3, C4, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.006
6. Others
 Sof(OA)=Sof(N00F)=Sof(N7)=Sof(C0)=Sof(H0)=Sof(C47)=Sof(H47)=Sof(C46)=
 Sof(C00{)=Sof(C01L)=Sof(H01L)=Sof(C48)=Sof(H48)=Sof(C45)=1-FVAR(1)
 Sof(O4)=Sof(N4)=Sof(N5)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=
 Sof(C27)=Sof(H27)=Sof(C28)=Sof(C23)=Sof(C29)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B), C39(H39A,H39B), C41(H41A,H41B)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5A), C9(H9), C11(H11), C12(H12), C0(H0),
 C47(H47), C01L(H01L), C48(H48), C24(H24), C25(H25), C26(H26), C27(H27),
 C31(H31), C33(H33), C34(H34)
7.c Fitted hexagon refined as free rotating group:
 C0(C47,C46,C00{,C01L,C48), C24(C25,C26,C27,C28,C23)
7.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C37(H37A,H37B,
 H37C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
7.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              59444
_shelx_hkl_checksum              70571
_shelx_fab_checksum              53708
_olex2_date_sample_data_collection 2023-10-13
_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 1.589
_oxdiff_exptl_absorpt_empirical_full_min 0.537