Benzylidene succinimides as 3C synthons for the asymmetric tandem Mannich reaction/transamidation of cyclic trifluoromethyl ketimines to obtain F<sub>3</sub>C-containing polycyclic dihydroquinazolinones.
Zhang, Xia-Yan; Dou, Pei-Hao; Lu, Wen-Ya; You, Yong; Zhao, Jian-Qiang; Wang, Zhen-Hua; Yuan, Wei-Cheng; Chemical communications (Cambridge, England) 57 (2021) 2927–2930; doi:10.1039/d0cc08131k

data_7127911
_publ_section_title
;
 Benzylidene succinimides as 3C synthons for the asymmetric tandem Mannich
 reaction/transamidation of cyclic trifluoromethyl ketimines to obtain
 F<sub>3</sub>C-containing polycyclic dihydroquinazolinones.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2927
_journal_page_last               2930
_journal_paper_doi               10.1039/d0cc08131k
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C16 H13 Cl N2 O3'
_chemical_formula_sum            'C16 H13 Cl N2 O3'
_chemical_formula_weight         316.73
_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             2020-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-24 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                84.687(3)
_cell_angle_beta                 74.704(3)
_cell_angle_gamma                69.975(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9537(4)
_cell_length_b                   9.3223(4)
_cell_length_c                   10.8300(5)
_cell_measurement_reflns_used    5072
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.922
_cell_measurement_theta_min      5.317
_cell_volume                     727.73(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      173.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8824
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.968
_diffrn_reflns_theta_min         4.392
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.600
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1296 before and 0.0732 after correction. The Ratio of minimum to maximum transmission is 0.7658. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0565P)^2^+0.3531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2326
_reflns_number_total             2767
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc08131k2.cif
_cod_data_source_block           2009239899_0m
_cod_depositor_comments
'Adding full bibliography for 7127911--7127912.cif.'
_cod_database_code               7127911
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.762
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              23787
_olex2_submission_special_instructions 'No special instructions were received'