One-Pot Tandem Assembly of Amides, Amines, and Ketones: Synthesis of C4-Quaternary 3,4- and 1,4-Dihydroquinazolines.
Campbell, Molly V.; Iretskii, Alexei V.; Mosey, R. Adam; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01308

data_4038706
_publ_section_title
;
 One-Pot Tandem Assembly of Amides, Amines, and Ketones: Synthesis of
 C4-Quaternary 3,4- and 1,4-Dihydroquinazolines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01308
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H28 N2 O3'
_chemical_formula_sum            'C31 H28 N2 O3'
_chemical_formula_weight         476.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-31
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.7454(2)
_cell_length_b                   13.7235(2)
_cell_length_c                   21.0126(3)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      70.10
_cell_measurement_theta_min      3.22
_cell_volume                     5117.18(12)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_diffrn_ambient_temperature      173(1)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            47117
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.121
_diffrn_reflns_theta_min         3.220
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0709 before and 0.0656 after correction.
The Ratio of minimum to maximum transmission is 0.9235.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       chunk
_exptl_crystal_F_000             2016
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 3209 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         9268
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0479P)^2^+0.4998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                8232
_reflns_number_total             9268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01308_si_002.cif
_cod_data_source_block           ram120a
_cod_database_code               4038706
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.806
_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:
 C10(H10A,H10B), C25(H25A,H25B), C10A(H10C,H10D), C25A(H25C,H25D)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31), C3A(H3A), C4A(H4A), C6A(H6A), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C17A(H17A), C20A(H20A), C21A(H21A), C22A(H22A),
 C23A(H23A), C24A(H24A), C27A(H27A), C28A(H28A), C29A(H29A), C30A(H30A),
 C31A(H31A)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C18(H18A,H18B,H18C), C11A(H11D,H11E,H11F), C18A(H18D,
 H18E,H18F)
;
_shelx_res_checksum              62699
_shelx_hkl_checksum              76733
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'RM-1-089 Ethyl acetate/ pentane vial'
_olex2_submission_special_instructions 'No special instructions were received'