One-pot synthesis of functionalized dihydropyridin-2-ones <i>via</i> carbene-catalyzed base-controlled [3+3] annulation reaction.
Wang, Zhan-Yong; Ma, Guoyang; Xu, Yaoyao; Wang, Qingqing; Zhang, Mengru; Ma, Xueji; Ma, Chenyang; Sun, Aili; Xia, Ran; Liu, Hongxin; Chemical communications (Cambridge, England) 60 (2024) 11327–11330; doi:10.1039/d4cc03521f

data_7133718
_publ_section_title
;
 One-pot synthesis of functionalized dihydropyridin-2-ones <i>via</i>
 carbene-catalyzed base-controlled [3+3] annulation reaction.
;
_journal_issue                   80
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11327
_journal_page_last               11330
_journal_paper_doi               10.1039/d4cc03521f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C31 H25 N O4 S'
_chemical_formula_sum            'C31 H25 N O4 S'
_chemical_formula_weight         507.58
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-10-13 deposited with the CCDC.	2024-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                91.730(4)
_cell_angle_beta                 99.279(4)
_cell_angle_gamma                92.540(3)
_cell_formula_units_Z            2
_cell_length_a                   8.671(2)
_cell_length_b                   10.576(2)
_cell_length_c                   14.370(3)
_cell_measurement_reflns_used    3526
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.287
_cell_measurement_theta_min      2.361
_cell_volume                     1298.3(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7874
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.447
_diffrn_reflns_theta_min         2.875
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0448 before and 0.0253 after correction.
The Ratio of minimum to maximum transmission is 0.9434.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0626P)^2^+0.3646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1352
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4216
_reflns_number_total             5627
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03521f2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7133718.cif.'
_cod_database_code               7133718
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.959
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C20(H20), C30(H30), C17(H17), C26(H26), C29(H29), C13(H13),
 C21(H21), C22(H22), C23(H23), C5(H5), C27(H27), C4(H4), C16(H16), C14(H14),
 C15(H15), C3(H3), C1(H1), C2(H2)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_shelx_res_checksum              98758
_shelx_hkl_checksum              45014
_olex2_submission_special_instructions 'No special instructions were received'