An organocatalytic asymmetric Mannich reaction for the synthesis of 3,3-disubstituted-3,4-dihydro-2-quinolones.
Mukhopadhyay, Soumendranath; Pan, Subhas Chandra; Organic & biomolecular chemistry 16 (2018) 5407–5411; doi:10.1039/c8ob01399c

data_7156310
_publ_section_title
;
 An organocatalytic asymmetric Mannich reaction for the synthesis of
 3,3-disubstituted-3,4-dihydro-2-quinolones.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5407
_journal_page_last               5411
_journal_paper_doi               10.1039/c8ob01399c
_journal_volume                  16
_journal_year                    2018
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C22 H21 F N3 O3, C H4 O'
_chemical_formula_sum            'C23 H25 F N3 O4'
_chemical_formula_weight         426.46
_chemical_name_systematic        Unknown
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2018-03-21 deposited with the CCDC.
2018-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.556(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8968(11)
_cell_length_b                   18.4254(17)
_cell_length_c                   10.7033(8)
_cell_measurement_reflns_used    1792
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2250
_cell_measurement_theta_min      3.6640
_cell_volume                     2280.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2760
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     -9.00  21.00   1.00    8.93    --  -17.33 -99.00  60.00   30
  2  \w    -48.00  16.00   1.00    8.93    --   20.84 -57.00 150.00   64
  3  \w    -86.00   1.00   1.00    8.93    --  -17.33 -57.00   0.00   87
  4  \w    -75.00 -21.00   1.00    8.93    --  -17.33 -57.00 -90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0274521000
_diffrn_orient_matrix_UB_12      -0.0343828000
_diffrn_orient_matrix_UB_13      0.0047099000
_diffrn_orient_matrix_UB_21      -0.0546782000
_diffrn_orient_matrix_UB_22      -0.0170430000
_diffrn_orient_matrix_UB_23      -0.0210059000
_diffrn_orient_matrix_UB_31      0.0046135000
_diffrn_orient_matrix_UB_32      0.0030264000
_diffrn_orient_matrix_UB_33      -0.0646507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8912
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             900
_exptl_crystal_recrystallization_method
'Dichloromethane and methanol solvents'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.6800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1468
_reflns_number_gt                2551
_reflns_number_total             4015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob01399c2.cif
_cod_data_source_block           snm-p2-cn-5-f
_cod_depositor_comments          'Adding full bibliography for 7156310.cif.'
_cod_original_cell_volume        2280.8(3)
_cod_database_code               7156310
_chemical_oxdiff_formula         'C21 H22 O3 N3 F1'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H24), C5(H5), C2(H2), C17(H17), C3(H3), C13(H13), C16(H16), C15(H15),
 C14(H14)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C21(H21A,H21B,
 H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 1.636
_oxdiff_exptl_absorpt_empirical_full_min 0.720