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_7160185
_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 ad
_chemical_formula_moiety         'C23 H21 N O2'
_chemical_formula_sum            'C23 H21 N O2'
_chemical_formula_weight         343.41
_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     iterative
_audit_creation_date             2024-04-11
_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                 102.6880(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.55890(10)
_cell_length_b                   9.73360(10)
_cell_length_c                   10.97970(10)
_cell_measurement_reflns_used    12523
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      78.2260
_cell_measurement_theta_min      5.2830
_cell_volume                     892.370(16)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      120.15
_diffrn_detector                 HPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'CMOS Photon 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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     -4.00  24.00   0.50    0.10    --  -51.83  19.00-180.00   56
  2  \w     -2.00  24.00   0.50    0.10    --  -51.83  19.00 -90.00   52
  3  \w     -1.00  25.00   0.50    0.10    --  -51.83  19.00 -60.00   52
  4  \w    -50.00 -13.00   0.50    0.10    --  -87.67  57.00  30.00   74
  5  \w    -53.00 -13.00   0.50    0.10    --  -87.67  57.00 120.00   80
  6  \w    -54.00  -4.00   0.50    0.10    --  -51.83 106.00  13.00  100
  7  \w    -89.00 -63.00   0.50    0.10    --  -87.67 106.00  13.00   52
  8  \w     38.00 112.00   0.50    0.10    --   52.33  77.00  60.00  148
  9  \w     98.00 129.00   0.50    0.10    --  102.07  38.00 -30.00   62
 10  \w     88.00 176.00   0.50    0.10    --  102.07  38.00 -60.00  176
 11  \w    124.00 154.00   0.50    0.10    --  107.25  19.00   1.64   60
 12  \w     69.00 107.00   0.50    0.10    --  107.25  19.00   1.64   76
 13  \w     69.00  97.00   0.50    0.10    --  107.25  17.00 169.51   56
 14  \w     80.00 133.00   0.50    0.10    --  107.25  18.00  38.92  106
 15  \w    137.00 163.00   0.50    0.10    --  107.25  15.00 -55.63   52
 16  \w     85.00 148.00   0.50    0.10    --  102.07  57.00-120.00  126
 17  \w     63.00 130.00   0.50    0.10    --  102.07  19.00-120.00  134
 18  \w     70.00 137.00   0.50    0.10    --  107.25  13.00 114.83  134
 19  \w     82.00 107.00   0.50    0.10    --  107.25   3.00  77.38   50
 20  \w    138.00 163.00   0.50    0.10    --  107.25   3.00  77.38   50
 21  \w     76.00 102.00   0.50    0.10    --  107.25  15.00 -55.63   52
 22  \w     57.00  82.00   0.50    0.10    --  107.25  11.00 -59.41   50
 23  \w   -139.00-114.00   0.50    0.10    --  -87.67-106.00 -86.00   50
 24  \w     41.00  68.00   0.50    0.10    --  107.25   3.00  77.38   54
 25  \w    -24.00  29.00   0.50    0.10    --   52.33 -19.00 120.00  106
 26  \w     41.00  91.00   0.50    0.10    --  107.25 -72.00  94.63  100
 27  \w     41.00  77.00   0.50    0.10    --  107.25 -79.00  81.54   72
 28  \w     41.00  67.00   0.50    0.10    --  107.25 -79.00  26.63   52
 29  \w     53.00  79.00   0.50    0.10    --  107.25 -71.00 -85.12   52
 30  \w     41.00  73.00   0.50    0.10    --  107.25 -77.00-122.00   64
 31  \w     40.00  83.00   0.50    0.10    --  107.25 -70.00-167.75   86
 32  \w     26.00  51.00   0.50    0.10    --  102.07 -38.00 -60.00   50
 33  \w     43.00 103.00   0.50    0.10    --  107.25 -70.00 -54.33  120
 34  \w     28.00  53.00   0.50    0.10    --  102.07 -57.00  60.00   50
 35  \w     26.00  51.00   0.50    0.10    --  102.07 -38.00 150.00   50
 36  \w     96.00 122.00   0.50    0.10    --  102.07 106.00  13.00   52
 37  \w     43.00  96.00   0.50    0.10    --  107.25 -81.00  13.32  106
 38  \w     72.00 105.00   0.50    0.10    --  102.07 -99.00  30.00   66
 39  \w     43.00  68.00   0.50    0.10    --  102.07 -99.00  30.00   50
 40  \w      6.00  80.00   0.50    0.10    --   52.33-106.00 -86.00  148
 41  \w     82.00 107.00   0.50    0.10    --  102.07-106.00 -86.00   50
 42  \w     72.00 105.00   0.50    0.10    --  102.07 -99.00 -90.00   66
 43  \w     76.00 105.00   0.50    0.10    --  102.07 -99.00-180.00   58
 44  \w     41.00  72.00   0.50    0.10    --  102.07 -99.00-180.00   62
 45  \w     39.00  66.00   0.50    0.10    --  102.07 -99.00 -90.00   54
 46  \w     41.00  67.00   0.50    0.10    --  107.25 -87.00-178.57   52
 47  \w     81.00 106.00   0.50    0.10    --  102.07 -99.00 -60.00   50
 48  \w     41.00  79.00   0.50    0.10    --  107.25 -88.00 128.36   76
 49  \w     41.00  74.00   0.50    0.10    --  102.07 -99.00 150.00   66
 50  \w    101.00 127.00   0.50    0.10    --  107.25 -88.00 138.70   52
 51  \w     41.00 102.00   0.50    0.10    --  107.25 -85.00  51.41  122
 52  \w     47.00  73.00   0.50    0.10    --  107.25 -85.00  66.68   52
 53  \w     96.00 133.00   0.50    0.10    --  107.25 -85.00  66.68   74
 54  \w     43.00  89.00   0.50    0.10    --  107.25 -84.00 155.91   92
 55  \w     89.00 115.00   0.50    0.10    --  107.25 -86.00 -82.62   52
 56  \w     47.00  73.00   0.50    0.10    --  107.25 -86.00 -82.62   52
 57  \w     48.00  85.00   0.50    0.10    --  107.25 -84.00-146.83   74
 58  \w    103.00 128.00   0.50    0.10    --  107.25 -87.00-178.57   50
;
_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_radiation_monochromator  'multilayer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14859
_diffrn_reflns_point_group_measured_fraction_full 0.866
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.829
_diffrn_reflns_theta_min         4.127
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69613
_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_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0257
_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^)+(0.0390P)^2^+0.1187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0665
_reflns_Friedel_coverage         0.610
_reflns_Friedel_fraction_full    0.716
_reflns_Friedel_fraction_max     0.686
_reflns_number_gt                3228
_reflns_number_total             3273
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01270d2.cif
_cod_data_source_block           vp_na284-3_3_auto
_cod_depositor_comments
'Adding full bibliography for 7160185--7160187.cif.'
_cod_database_code               7160185
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.940
_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), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 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
;