Triflic acid-promoted post-Ugi condensation for the assembly of 2,6-diarylmorpholin-3-ones.
Amire, Niyaz; Almagambetova, Kamila M.; Turlykul, Assel; Taishybay, Aidyn; Nuroldayeva, Gulzat; Belyaev, Andrey; Peshkov, Anatoly A.; Utepbergenov, Darkhan; Peshkov, Vsevolod A.; Organic & biomolecular chemistry 22 (2024) 9379–9387; doi:10.1039/d4ob01270d

data_7160186
_publ_section_title
;
 Triflic acid-promoted post-Ugi condensation for the assembly of
 2,6-diarylmorpholin-3-ones.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9379
_journal_page_last               9387
_journal_paper_doi               10.1039/d4ob01270d
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C23 H19 N O2'
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-05
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2024-07-23 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.234(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.39260(10)
_cell_length_b                   9.5816(2)
_cell_length_c                   16.9103(4)
_cell_measurement_reflns_used    9514
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      77.8820
_cell_measurement_theta_min      5.2800
_cell_volume                     873.74(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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     43.00  69.00   0.50    0.10    --  102.07-125.00-150.00   52
  2  \w     65.00 105.00   0.50    0.10    --  102.07 -99.00 -30.00   80
  3  \w     65.00  91.00   0.50    0.10    --  102.07-114.00  59.00   52
  4  \w     81.00 106.00   0.50    0.10    --  102.07 -99.00  90.00   50
  5  \w     78.00 104.00   0.50    0.10    --  102.07 -99.00  60.00   52
  6  \w     35.00  65.00   0.50    0.10    --  102.07 -99.00  90.00   60
  7  \w     15.00  97.00   0.50    0.10    --   52.08-114.00  59.00  164
  8  \w     70.00  99.00   0.50    0.10    --  102.07 -99.00 -60.00   58
  9  \w     92.00 117.00   0.50    0.10    --  107.25 -84.00-145.81   50
 10  \w     43.00  77.00   0.50    0.10    --  107.25 -84.00-145.81   68
 11  \w     42.00  67.00   0.50    0.10    --  107.25 -82.00-171.70   50
 12  \w     42.00  67.00   0.50    0.10    --  107.25 -82.00 -56.58   50
 13  \w     45.00  71.00   0.50    0.10    --  107.25 -81.00 -68.56   52
 14  \w     87.00 112.00   0.50    0.10    --  107.25 -81.00 -68.56   50
 15  \w    106.00 136.00   0.50    0.10    --  107.25 -86.00  25.78   60
 16  \w     94.00 120.00   0.50    0.10    --  107.25 -85.00 156.28   52
 17  \w     54.00  82.00   0.50    0.10    --  107.25 -78.00 121.68   56
 18  \w     39.00  64.00   0.50    0.10    --  107.25 -74.00 106.40   50
 19  \w     96.00 121.00   0.50    0.10    --  107.25 -74.00 106.40   50
 20  \w     41.00  87.00   0.50    0.10    --  107.25 -72.00  77.44   92
 21  \w     41.00  67.00   0.50    0.10    --  107.25 -73.00  -3.73   52
 22  \w     67.00  93.00   0.50    0.10    --  107.25 -69.00-139.77   52
 23  \w     42.00  93.00   0.50    0.10    --  107.25 -71.00-122.77  102
 24  \w     45.00  74.00   0.50    0.10    --  102.07 -57.00 -90.00   58
 25  \w     43.00 120.00   0.50    0.10    --  107.25 -76.00 -36.25  154
 26  \w     92.00 117.00   0.50    0.10    --  107.25 -73.00  -3.73   50
 27  \w     42.00  89.00   0.50    0.10    --  107.25 -68.00 128.76   94
 28  \w     26.00  51.00   0.50    0.10    --  102.07 -38.00  90.00   50
 29  \w     37.00  71.00   0.50    0.10    --  102.07 -57.00  30.00   68
 30  \w    -20.00  13.00   0.50    0.10    --   52.08 -19.00 120.00   66
 31  \w     25.00  50.00   0.50    0.10    --  102.07 -38.00   0.00   50
 32  \w     26.00  51.00   0.50    0.10    --  102.07 -38.00 -60.00   50
 33  \w     28.00  53.00   0.50    0.10    --  102.07 -57.00-150.00   50
 34  \w     26.00  51.00   0.50    0.10    --  102.07 -38.00-180.00   50
 35  \w     46.00  96.00   0.50    0.10    --  107.25  13.00-163.63  100
 36  \w     68.00 114.00   0.50    0.10    --  107.25  19.00 -64.14   92
 37  \w     89.00 174.00   0.50    0.10    --  102.07  38.00 -60.00  170
 38  \w    142.00 174.00   0.50    0.10    --  107.25  17.00 -33.14   64
 39  \w    138.00 163.00   0.50    0.10    --  107.25  19.00 -64.14   50
 40  \w    100.00 126.00   0.50    0.10    --  107.25  17.00 -33.14   52
 41  \w    142.00 176.00   0.50    0.10    --  107.25  15.00  19.69   68
 42  \w     88.00 123.00   0.50    0.10    --  102.07  38.00  90.00   70
 43  \w     63.00  91.00   0.50    0.10    --  107.25  13.00  73.52   56
 44  \w     66.00  95.00   0.50    0.10    --  107.25  15.00  19.69   58
 45  \w    140.00 165.00   0.50    0.10    --  107.25  16.00 115.57   50
 46  \w    113.00 176.00   0.50    0.10    --  107.25  13.00  73.52  126
 47  \w    112.00 137.00   0.50    0.10    --  107.25  13.00-163.63   50
 48  \w     29.00 115.00   0.50    0.10    --   52.08  77.00 120.00  172
 49  \w     80.00 124.00   0.50    0.10    --  102.07 125.00 120.00   88
 50  \w     88.00 123.00   0.50    0.10    --  102.07 114.00 150.00   70
 51  \w    127.00 153.00   0.50    0.10    --  102.07 114.00 150.00   52
 52  \w     -1.00  24.00   0.50    0.10    --  -51.83  19.00 120.00   50
 53  \w     -3.00  25.00   0.50    0.10    --  -51.83  19.00  90.00   56
 54  \w     -2.00  25.00   0.50    0.10    --  -51.83  19.00  60.00   54
 55  \w    -52.00 -22.00   0.50    0.10    --  -87.67  57.00 -60.00   60
 56  \w    -48.00 -14.00   0.50    0.10    --  -87.67  57.00 -90.00   68
 57  \w     -1.00  25.00   0.50    0.10    --  -51.83  19.00 -90.00   52
 58  \w   -101.00 -62.00   0.50    0.10    --  -87.67 114.00 150.00   78
 59  \w    -75.00 -50.00   0.50    0.10    --  -51.83 114.00 150.00   50
 60  \w   -131.00 -81.00   0.50    0.10    --  -87.67-114.00  59.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2035890000
_diffrn_orient_matrix_UB_12      -0.1057027000
_diffrn_orient_matrix_UB_13      0.0226388000
_diffrn_orient_matrix_UB_21      0.0853678000
_diffrn_orient_matrix_UB_22      -0.0051162000
_diffrn_orient_matrix_UB_23      -0.0867803000
_diffrn_orient_matrix_UB_31      0.1812460000
_diffrn_orient_matrix_UB_32      0.1210424000
_diffrn_orient_matrix_UB_33      0.0161124000
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13716
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.255
_diffrn_reflns_theta_min         2.613
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1280 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0571P)^2^+0.0492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.824
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                3221
_reflns_number_total             3373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01270d2.cif
_cod_data_source_block           vp_6a_2_auto
_cod_depositor_comments
'Adding full bibliography for 7160185--7160187.cif.'
_cod_database_code               7160186
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_chemical_oxdiff_usercomment     'colorless plates, etoac'
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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 2.323
_oxdiff_exptl_absorpt_empirical_full_min 0.530