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_7160187
_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 H23 N O'
_chemical_formula_sum            'C23 H23 N O'
_chemical_formula_weight         329.42
_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             2024-04-11
_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                 101.3440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.43560(10)
_cell_length_b                   9.11270(10)
_cell_length_c                   11.9169(2)
_cell_measurement_reflns_used    15602
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.9800
_cell_measurement_theta_min      3.7510
_cell_volume                     898.17(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (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      120.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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     76.00 103.00   0.50    0.50    --   53.18  42.00-126.00   54
  2  \w      3.00  55.00   0.50    0.50    --   53.18 -42.00  80.00  104
  3  \w     97.00 148.00   0.50    0.50    --  101.85  42.00-126.00  102
  4  \w     36.00 107.00   0.50    0.50    --  101.85 -42.00  80.00  142
  5  \w    -33.00  -6.00   0.50    0.50    --    6.00 115.00 -65.77   54
  6  \w    -11.00  25.00   0.50    0.50    --   18.00  98.00 123.14   72
  7  \w     -2.00  23.00   0.50    0.50    --   26.00  97.00  46.41   50
  8  \w      7.00  32.00   0.50    0.50    --   34.00  94.00 -58.10   50
  9  \w     15.00  40.00   0.50    0.50    --   38.00  88.00  71.78   50
 10  \w     31.00  56.00   0.50    0.50    --   46.00  76.00 -48.08   50
 11  \w     30.00  59.00   0.50    0.50    --   46.00  76.00-142.77   58
 12  \w     35.00  61.00   0.50    0.50    --   50.00  77.00 127.96   52
 13  \w     36.00  61.00   0.50    0.50    --   52.83  77.00 150.00   50
 14  \w     36.00  61.00   0.50    0.50    --   52.83  77.00 -30.00   50
 15  \w     37.00  62.00   0.50    0.50    --   53.18  77.00   0.00   50
 16  \w     38.00  64.00   0.50    0.50    --   53.18  77.00  30.00   52
 17  \w     -6.00  69.00   0.50    0.50    --   53.18 -77.00  60.00  150
 18  \w     37.00  62.00   0.50    0.50    --   53.18  77.00-120.00   50
 19  \w     34.00  86.00   0.50    0.50    --   53.18-125.00 -90.00  104
 20  \w     72.00  98.00   0.50    0.50    --   53.18-125.00-150.00   52
 21  \w     35.00  68.00   0.50    0.50    --   53.18-125.00-150.00   66
 22  \w     34.00  77.00   0.50    0.50    --   53.18-125.00 -30.00   86
 23  \w     34.00  98.00   0.50    0.50    --   53.18-125.00  30.00  128
 24  \w     86.00 112.00   0.50    0.50    --   53.18  77.00  90.00   52
 25  \w     37.00  63.00   0.50    0.50    --   53.18  77.00  90.00   52
 26  \w     44.00  69.00   0.50    0.50    --   58.00  72.00  58.22   50
 27  \w     48.00  74.00   0.50    0.50    --   62.00  72.00 -82.13   52
 28  \w     49.00  86.00   0.50    0.50    --   62.00  76.00 -29.49   74
 29  \w     49.00  75.00   0.50    0.50    --   62.00  73.00  62.24   52
 30  \w     84.00 109.00   0.50    0.50    --   62.00  67.00-119.68   50
 31  \w     50.00  76.00   0.50    0.50    --   62.00  67.00-119.68   52
 32  \w     98.00 123.00   0.50    0.50    --   62.00  77.00-176.35   50
 33  \w     91.00 124.00   0.50    0.50    --   62.00  76.00 -29.49   66
 34  \w     47.00  81.00   0.50    0.50    --   62.00  77.00-176.35   68
 35  \w     47.00  72.00   0.50    0.50    --   62.00  76.00 168.54   50
 36  \w     52.00 105.00   0.50    0.50    --   66.00  72.00-103.41  106
 37  \w     55.00  92.00   0.50    0.50    --   66.00  70.00  23.75   74
 38  \w    105.00 131.00   0.50    0.50    --   70.00  76.00 106.56   52
 39  \w     54.00  82.00   0.50    0.50    --   70.00  76.00 106.56   56
 40  \w     60.00  86.00   0.50    0.50    --   74.00  72.00  74.54   52
 41  \w     59.00 117.00   0.50    0.50    --   74.00  74.00 -82.75  116
 42  \w     89.00 133.00   0.50    0.50    --   74.00  72.00  74.54   88
 43  \w     72.00  98.00   0.50    0.50    --   78.00  57.00 144.51   52
 44  \w    110.00 147.00   0.50    0.50    --   78.00  54.00  18.09   74
 45  \w     70.00  96.00   0.50    0.50    --   78.00  54.00  18.09   52
 46  \w    115.00 143.00   0.50    0.50    --   78.00  57.00 144.51   56
 47  \w     85.00 135.00   0.50    0.50    --  101.85  77.00  30.00  100
 48  \w     95.00 125.00   0.50    0.50    --  101.85  57.00 -30.00   60
 49  \w     30.00 106.00   0.50    0.50    --  101.85 -37.00 150.00  152
 50  \w    127.00 161.00   0.50    0.50    --  101.85  77.00  90.00   68
 51  \w     85.00 161.00   0.50    0.50    --  101.85  77.00  60.00  152
 52  \w     86.00 159.00   0.50    0.50    --  101.85  77.00-180.00  146
 53  \w     38.00 110.00   0.50    0.50    --  101.85-125.00 120.00  144
 54  \w     85.00 133.00   0.50    0.50    --  101.85  77.00 150.00   96
 55  \w     78.00 103.00   0.50    0.50    --  101.85 -99.00  60.00   50
 56  \w     85.00 123.00   0.50    0.50    --  101.85  77.00  90.00   76
 57  \w     65.00 108.00   0.50    0.50    --  101.85-125.00 -60.00   86
 58  \w     96.00 135.00   0.50    0.50    --  101.85  57.00-120.00   78
 59  \w    110.00 158.00   0.50    0.50    --  101.85 125.00 120.00   96
 60  \w     94.00 153.00   0.50    0.50    --  101.85  57.00 -60.00  118
 61  \w     91.00 161.00   0.50    0.50    --  101.85  77.00 120.00  140
 62  \w     88.00 162.00   0.50    0.50    --  101.85  77.00-120.00  148
 63  \w     44.00 104.00   0.50    0.50    --  101.85 -99.00 -30.00  120
 64  \w     44.00  70.00   0.50    0.50    --  101.85 -99.00  60.00   52
 65  \w     85.00 138.00   0.50    0.50    --  101.85  77.00 -30.00  106
 66  \w     57.00 100.00   0.50    0.50    --  101.85 -99.00-180.00   86
 67  \w     86.00 112.00   0.50    0.50    --  101.85  77.00-150.00   52
 68  \w     85.00 111.00   0.50    0.50    --  101.85  77.00 -90.00   52
 69  \w     85.00 111.00   0.50    0.50    --  101.85  77.00 -60.00   52
 70  \w     85.00 134.00   0.50    0.50    --  101.85  77.00   0.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0064024000
_diffrn_orient_matrix_UB_12      0.1459467000
_diffrn_orient_matrix_UB_13      0.0641704000
_diffrn_orient_matrix_UB_21      -0.1862264000
_diffrn_orient_matrix_UB_22      -0.0060381000
_diffrn_orient_matrix_UB_23      -0.0268603000
_diffrn_orient_matrix_UB_31      0.0022423000
_diffrn_orient_matrix_UB_32      -0.0851569000
_diffrn_orient_matrix_UB_33      0.1119272000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18692
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.264
_diffrn_reflns_theta_min         3.783
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (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    1.218
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1621 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_coef       0.0054(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0277
_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^)+(0.0257P)^2^+0.1633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0677
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                3593
_reflns_number_total             3675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01270d2.cif
_cod_data_source_block           na281_auto
_cod_depositor_comments
'Adding full bibliography for 7160185--7160187.cif.'
_cod_database_code               7160187
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'c20 h20 n2'
_chemical_oxdiff_usercomment     plate
_shelx_estimated_absorpt_t_max   0.978
_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), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), 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 1.571
_oxdiff_exptl_absorpt_empirical_full_min 0.742