CCC pincer Ru complex-catalyzed C-H vinylation/6π-E-cyclization of aldimines for constructing 4<i>H</i>-pyrido[1,2-<i>a</i>]pyrimidines.
Cai, Heng; Tu, Yong-Qiang; Niu, Qiang; Xie, Wen-Ping; Wang, Bin; Lu, Ka; Li, Zi-Hao; Zhang, Fu-Min; Zhang, Xiao-Ming; Chemical science 15 (2024) 16216–16221; doi:10.1039/d4sc05067c

data_1572489
_publ_section_title
;
 CCC pincer Ru complex-catalyzed C-H vinylation/6&#x3c0;-E-cyclization of
 aldimines for constructing 4<i>H</i>-pyrido[1,2-<i>a</i>]pyrimidines.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              16216
_journal_page_last               16221
_journal_paper_doi               10.1039/d4sc05067c
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H24 N2'
_chemical_formula_sum            'C24 H24 N2'
_chemical_formula_weight         340.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-06
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-03-18 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3172(3)
_cell_length_b                   13.2929(4)
_cell_length_c                   15.5466(6)
_cell_measurement_reflns_used    4033
_cell_measurement_temperature    300.77(10)
_cell_measurement_theta_max      73.6910
_cell_measurement_theta_min      3.3210
_cell_volume                     1925.49(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (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      300.77(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 0.932
_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     71.00 107.00   0.50    1.74    --  111.87-113.00 -85.00   72
  2  \w     40.00  65.00   0.50    1.74    --  111.87 -61.00  90.00   50
  3  \w    -11.00  15.00   0.50    0.43    --   45.30 -19.00 120.00   52
  4  \w     27.00 115.00   0.50    0.43    --   45.30  51.00 -70.00  176
  5  \w     97.00 161.00   0.50    1.74    --  111.87  51.00 -70.00  128
  6  \w    -25.00  16.00   0.50    0.43    --   45.30 -19.00   0.00   82
  7  \w    -92.00 -29.00   0.50    1.74    -- -100.00  71.00 123.00  126
  8  \w    -52.00 -27.00   0.50    1.74    -- -100.00  45.00 120.00   50
  9  \w    -54.00 -29.00   0.50    1.74    -- -100.00  45.00  90.00   50
 10  \w    -74.00 -35.00   0.50    1.74    -- -100.00  61.00  90.00   78
 11  \w    -72.00 -46.00   0.50    1.74    -- -100.00  61.00-180.00   52
 12  \w    -50.00 -25.00   0.50    1.74    -- -100.00  45.00-120.00   50
 13  \w   -163.00 -91.00   0.50    1.74    -- -100.00 -94.00 120.00  144
 14  \w    -75.00 -49.00   0.50    0.43    --  -45.30-179.00   0.00   52
 15  \w    -17.00  55.00   1.00    0.43    --   45.27 -51.00 143.00   72
 16  \w    -51.00 -25.00   1.00    1.74    -- -100.00  45.00 150.00   26
 17  \w    -62.00 -30.00   1.00    1.74    -- -100.00  61.00-150.00   32
 18  \w    -61.00 -35.00   1.00    1.74    -- -100.00  51.00 -70.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1229372000
_diffrn_orient_matrix_UB_12      -0.0424426000
_diffrn_orient_matrix_UB_13      -0.0595550000
_diffrn_orient_matrix_UB_21      -0.1059324000
_diffrn_orient_matrix_UB_22      -0.0668886000
_diffrn_orient_matrix_UB_23      -0.0425951000
_diffrn_orient_matrix_UB_31      -0.0314491000
_diffrn_orient_matrix_UB_32      0.0595413000
_diffrn_orient_matrix_UB_33      -0.0898659000
_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  0.0315
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7964
_diffrn_reflns_point_group_measured_fraction_full 0.853
_diffrn_reflns_point_group_measured_fraction_max 0.779
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.376
_diffrn_reflns_theta_min         4.376
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 994 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3184
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+0.0792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_full    0.698
_reflns_Friedel_fraction_max     0.615
_reflns_number_gt                2871
_reflns_number_total             3184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05067c2.cif
_cod_data_source_block           caiheng_1106_auto
_cod_depositor_comments
'Adding full bibliography for 1572486--1572491.cif.'
_cod_database_code               1572489
_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
2.a Secondary CH2 refined with riding coordinates:
 C24(H00A,H00E), C17(H00K,H00L)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H008), C14(H009), C18(H00B), C20(H00C), C22(H00D), C3(H00F), C13(H00G),
 C7(H00H), C15(H00I), C2(H00J), C9(H00M), C19(H00N), C5(H00O), C21(H00P)
2.c Idealised Me refined as rotating group:
 C11(H00Q,H00R,H00S), C23(H00T,H00U,H00V)
;
_shelx_res_checksum              56954
_shelx_hkl_checksum              21249
_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 1.313
_oxdiff_exptl_absorpt_empirical_full_min 0.777