Ru(ii)-catalyzed oxidative (4+3) C–H/C–H annulation of 2-aryl-4H-pyrido[1,2-a]pyrimidin-4-ones with allyl alcohol
Jangir, Tarun; Nipate, Dhananjay S.; Rangan, Krishnan; Kumar, Anil; Chemical Communications 61 (2025) 5762–5765; doi:10.1039/D5CC00318K

data_7134328
_publ_section_title
;
 Ru(ii)-catalyzed oxidative (4+3) C--H/C--H annulation of
 2-aryl-4H-pyrido[1,2-a]pyrimidin-4-ones with allyl alcohol
;
_journal_issue                   31
_journal_name_full               'Chemical Communications'
_journal_page_first              5762
_journal_page_last               5765
_journal_paper_doi               10.1039/D5CC00318K
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C17 H11 Cl N2 O'
_chemical_formula_sum            'C17 H11 Cl N2 O'
_chemical_formula_weight         294.73
_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             2024-04-04
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-03 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.449(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.4063(6)
_cell_length_b                   4.2344(2)
_cell_length_c                   15.0153(5)
_cell_measurement_reflns_used    5305
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.0490
_cell_measurement_theta_min      1.9890
_cell_volume                     1297.03(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.971
_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    -14.00  43.00   0.50   20.22    --   -5.30  17.00-115.00  114
  2  \w    -27.00  18.00   0.50   20.22    --    5.30  17.00-115.00   90
  3  \w    -95.00  20.00   0.50   20.22    --   -5.30 -77.00   0.00  230
  4  \w     19.00  86.00   0.50   20.22    --    5.30  77.00-120.00  134
  5  \w    -84.00  29.00   0.50   20.22    --    5.30 -77.00 -60.00  226
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0338616000
_diffrn_orient_matrix_UB_12      0.0377365000
_diffrn_orient_matrix_UB_13      0.0007226000
_diffrn_orient_matrix_UB_21      0.0000741000
_diffrn_orient_matrix_UB_22      -0.0085366000
_diffrn_orient_matrix_UB_23      -0.0471592000
_diffrn_orient_matrix_UB_31      -0.0078337000
_diffrn_orient_matrix_UB_32      0.1630959000
_diffrn_orient_matrix_UB_33      -0.0026920000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8551
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.294
_diffrn_reflns_theta_min         1.997
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0498P)^2^+0.3965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1024
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1775
_reflns_number_total             2144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00318k2.cif
_cod_data_source_block           dsn1221_rk20240404
_cod_depositor_comments          'Adding full bibliography for 7134328.cif.'
_cod_database_code               7134328
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N Cl'
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.904
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C16(H16),
 C17(H17)
;
_shelx_res_checksum              60257
_shelx_hkl_checksum              19099
_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 5.282
_oxdiff_exptl_absorpt_empirical_full_min 0.417