N-Heterocyclic carbene-catalyzed enantioselective annulation of 2-amino-1<i>H</i>-indoles and bromoenals for the synthesis of chiral 2-aryl-2,3-dihydropyrimido[1,2-<i>a</i>]indol-4 (1<i>H</i>)-ones.
Zhao, Jianbo; Wu, Min; Luo, Jiamin; Shi, Lei; Li, Hao; Organic & biomolecular chemistry 21 (2023) 6675–6680; doi:10.1039/d3ob01006f

data_7159518
_publ_section_title
;
 N-Heterocyclic carbene-catalyzed enantioselective annulation of
 2-amino-1<i>H</i>-indoles and bromoenals for the synthesis of chiral
 2-aryl-2,3-dihydropyrimido[1,2-<i>a</i>]indol-4 (1<i>H</i>)-ones.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6675
_journal_page_last               6680
_journal_paper_doi               10.1039/d3ob01006f
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H13 N3 O'
_chemical_formula_weight         287.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-05-03 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.864(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4603(2)
_cell_length_b                   20.5881(9)
_cell_length_c                   12.9406(6)
_cell_measurement_reflns_used    5458
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      137.743
_cell_measurement_theta_min      8.083
_cell_volume                     1451.44(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19539
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.985
_diffrn_reflns_theta_min         4.041
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 1569 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         5271
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0644
_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^)+(0.1010P)^2^+0.1783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1932
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4026
_reflns_number_total             5271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01006f2.cif
_cod_data_source_block           d8v23073
_cod_depositor_comments          'Adding full bibliography for 7159518.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159518
_shelx_estimated_absorpt_t_min   0.911
_shelx_estimated_absorpt_t_max   0.961
_shelxl_version_number           2013-4
_shelx_res_checksum              85418