Synthesis of 4-(trichloromethyl)pyrido[2′,1′:3,4]pyrazino[2,1-b]quinazolinones through a cyclized dearomatization and trichloromethylation cascade strategy
Zhang, Xu; Wei, Meng-Yan; Su, Jun-Cheng; Liang, Cui; Pan, Cheng-Xue; Su, Gui-Fa; Mo, Dong-Liang; Organic & Biomolecular Chemistry 22 (2024) 1386–1390; doi:10.1039/D3OB02084C

data_7159777
_publ_section_title
;
 Synthesis of
 4-(trichloromethyl)pyrido[2&#x2032;,1&#x2032;:3,4]pyrazino[2,1-b]quinazolinones
 through a cyclized dearomatization and trichloromethylation cascade
 strategy
;
_journal_issue                   7
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1386
_journal_page_last               1390
_journal_paper_doi               10.1039/D3OB02084C
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C17 H11 Cl2 N3 O'
_chemical_formula_sum            'C17 H11 Cl2 N3 O'
_chemical_formula_weight         344.19
_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             2023-06-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-28 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.901(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9897(4)
_cell_length_b                   4.88490(10)
_cell_length_c                   21.3648(5)
_cell_measurement_reflns_used    6403
_cell_measurement_temperature    297.69(10)
_cell_measurement_theta_max      77.2330
_cell_measurement_theta_min      3.1110
_cell_volume                     1488.66(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.69(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.909
_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     96.00 158.00   0.50    2.10    --  108.37  21.00  99.00  124
  2  \w     55.00  80.00   0.50    0.88    --   48.32  21.00  99.00   50
  3  \w    -18.00   7.00   0.50    0.88    --   48.32 -21.00 -67.00   50
  4  \w     44.00  71.00   0.50    2.10    --  108.37 -77.00-150.00   54
  5  \w     78.00 104.00   0.50    2.10    --  108.37 -77.00-150.00   52
  6  \w     36.00  61.00   0.50    2.10    --  108.37 -57.00 -90.00   50
  7  \w     39.00  66.00   0.50    2.10    --  108.37 -57.00 -60.00   54
  8  \w     37.00  62.00   0.50    2.10    --  108.37 -57.00  90.00   50
  9  \w     40.00  66.00   0.50    2.10    --  108.37 -57.00 120.00   52
 10  \w     60.00 103.00   0.50    2.10    --  108.37 -99.00  90.00   86
 11  \w    -27.00  16.00   0.50    0.88    --  -48.32  21.00  99.00   86
 12  \w     -6.00  27.00   0.50    0.88    --  -48.32  19.00 120.00   66
 13  \w    -27.00  25.00   0.50    0.88    --  -48.32  19.00-120.00  104
 14  \w    -66.00 -19.00   0.50    2.10    --  -91.75  57.00 -90.00   94
 15  \w    -54.00 -21.00   0.50    2.10    --  -91.75  77.00-150.00   66
 16  \w    -64.00 -19.00   0.50    2.10    --  -91.75  57.00-180.00   90
 17  \w    -99.00 -70.00   0.50    2.10    --  -91.75  77.00-150.00   58
 18  \w    -64.00 -35.00   0.50    2.10    --  -91.75  57.00  60.00   58
 19  \w    -56.00 -22.00   0.50    2.10    --  -91.75  57.00  90.00   68
 20  \w    -85.00 -30.00   0.50    2.10    --  -91.75 125.00 150.00  110
 21  \w   -123.00 -38.00   0.50    0.88    --  -48.32 -21.00 -67.00  170
 22  \w   -112.00 -86.00   0.50    0.88    --  -48.32 -37.00-150.00   52
 23  \w   -134.00 -81.00   0.50    2.10    --  -91.75 -21.00 -67.00  106
 24  \w   -151.00 -79.00   0.50    2.10    --  -91.75 -19.00   0.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0025179000
_diffrn_orient_matrix_UB_12      -0.0855163000
_diffrn_orient_matrix_UB_13      -0.0688321000
_diffrn_orient_matrix_UB_21      -0.1076610000
_diffrn_orient_matrix_UB_22      -0.0256750000
_diffrn_orient_matrix_UB_23      -0.0232738000
_diffrn_orient_matrix_UB_31      -0.0084411000
_diffrn_orient_matrix_UB_32      0.3024576000
_diffrn_orient_matrix_UB_33      -0.0214455000
_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  0.0376
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9563
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.464
_diffrn_reflns_theta_min         3.098
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0457P)^2^+0.5096P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2442
_reflns_number_total             2880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02084c2.cif
_cod_data_source_block           20230621-mdl-zx-3_auto
_cod_depositor_comments          'Adding full bibliography for 7159777.cif.'
_cod_database_code               7159777
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl'
_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:
 C009(H009), C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00C)
;
_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 1.465
_oxdiff_exptl_absorpt_empirical_full_min 0.775