Preparation of 3,5-diarylsubstituted 5-hydroxy-1,5-dihydro-2H-pyrrol-2-ones via base-assisted cyclization of 3-cyanoketones
Aksenov, Nicolai A.; Aksenov, Dmitrii A.; Kurenkov, Igor A.; Aksenov, Alexander V.; Skomorokhov, Anton A.; Prityko, Lidiya A.; Rubin, Michael; RSC Advances 11 (2021) 16236–16245; doi:10.1039/D1RA02279B

data_7242739
_publ_section_title
;
 Preparation of 3,5-diarylsubstituted
 5-hydroxy-1,5-dihydro-2H-pyrrol-2-ones via base-assisted cyclization of
 3-cyanoketones
;
_journal_issue                   27
_journal_name_full               'RSC Advances'
_journal_page_first              16236
_journal_page_last               16245
_journal_paper_doi               10.1039/D1RA02279B
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C17 H15 N O3'
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-03-10 deposited with the CCDC.	2021-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.5730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.89340(10)
_cell_length_b                   6.18360(10)
_cell_length_c                   20.9171(2)
_cell_measurement_reflns_used    14065
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7920
_cell_measurement_theta_min      4.1300
_cell_volume                     1385.06(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_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      5.00  42.00   1.00    1.50    --   38.00  80.00  26.05   37
  2  \w    -21.00  74.00   1.00    1.50    --   41.72 -77.00-120.00   95
  3  \w     17.00 116.00   1.00    1.50    --   41.72  38.00 -60.00   99
  4  \w     17.00 116.00   1.00    1.50    --   41.72  38.00   0.00   99
  5  \w    -21.00  74.00   1.00    1.50    --   41.72 -77.00 150.00   95
  6  \w     13.00  42.00   1.00    1.50    --   46.00  80.00  87.18   29
  7  \w     30.00 137.00   1.00    1.50    --   62.00  74.00 -25.02  107
  8  \w     30.00 137.00   1.00    1.50    --   62.00  74.00  42.52  107
  9  \w     35.00 140.00   1.00    1.50    --   66.00  72.00 -20.89  105
 10  \w     35.00 140.00   1.00    1.50    --   66.00  72.00   5.51  105
 11  \w     38.00 145.00   1.00    1.50    --   70.00  73.00 -78.56  107
 12  \w     38.00 145.00   1.00    1.50    --   70.00  73.00  57.23  107
 13  \w     40.00 143.00   1.00    1.50    --   70.00  64.00-124.62  103
 14  \w     43.00 148.00   1.00    1.50    --   74.00  72.00 -57.48  105
 15  \w     83.00 178.00   1.00    6.00    --  112.00  61.00   0.00   95
 16  \w     30.00 106.00   1.00    6.00    --  112.00 -95.00  90.00   76
 17  \w     83.00 178.00   1.00    6.00    --  112.00  61.00-120.00   95
 18  \w    104.00 178.00   1.00    6.00    --  112.00 111.00   0.00   74
 19  \w     68.00 178.00   1.00    6.00    --  112.00  18.00 -83.02  110
 20  \w     36.00 145.00   1.00    6.00    --  112.00 -77.00 120.00  109
 21  \w     40.00 118.00   1.00    6.00    --  112.00-132.00  24.00   78
 22  \w     83.00 178.00   1.00    6.00    --  112.00  61.00 -60.00   95
 23  \w     83.00 178.00   1.00    6.00    --  112.00  61.00  30.00   95
 24  \w     40.00 115.00   1.00    6.00    --  112.00 -61.00  90.00   75
 25  \w     84.00 109.00   1.00    6.00    --  112.00  61.00  60.00   25
 26  \w     42.00 108.00   1.00    6.00    --  112.00-111.00-150.00   66
 27  \w     39.00  86.00   1.00    6.00    --  112.00 -95.00 120.00   47
 28  \w    147.00 176.00   1.00    6.00    --  112.00  61.00 -30.00   29
 29  \w     62.00  88.00   1.00    6.00    --  112.00-111.00 120.00   26
 30  \w     91.00 123.00   1.00    6.00    --  112.00  45.00 -30.00   32
 31  \w     84.00 110.00   1.00    6.00    --  112.00  61.00 -30.00   26
 32  \w    107.00 141.00   1.00    6.00    --  112.00 111.00  90.00   34
 33  \w    148.00 173.00   1.00    6.00    --  112.00  61.00 -90.00   25
 34  \w     87.00 126.00   1.00    6.00    --  112.00  45.00   0.00   39
 35  \w     84.00 109.00   1.00    6.00    --  112.00  61.00 -90.00   25
 36  \w    104.00 130.00   1.00    6.00    --  112.00 111.00 -30.00   26
 37  \w    150.00 176.00   1.00    6.00    --  112.00 111.00 -30.00   26
 38  \w     93.00 139.00   1.00    6.00    --  112.00 178.00 120.00   46
 39  \w     86.00 140.00   1.00    6.00    --  112.00  45.00 -90.00   54
 40  \w    145.00 170.00   1.00    6.00    --  112.00  45.00 -90.00   25
 41  \w    142.00 174.00   1.00    6.00    --  112.00 111.00  30.00   32
 42  \w     87.00 112.00   1.00    6.00    --  112.00  45.00  30.00   25
 43  \w     37.00 108.00   1.00    6.00    --  112.00-111.00  90.00   71
 44  \w     85.00 163.00   1.00    6.00    --  112.00 -15.00 120.00   78
 45  \w     84.00 109.00   1.00    6.00    --  112.00-111.00-120.00   25
 46  \w     73.00  99.00   1.00    6.00    --  112.00   5.00   4.24   26
 47  \w    126.00 165.00   1.00    6.00    --  112.00   5.00   4.24   39
 48  \w    151.00 176.00   1.00    6.00    --  112.00  30.00-180.00   25
 49  \w     79.00 104.00   1.00    6.00    --  112.00 -95.00  30.00   25
 50  \w     89.00 132.00   1.00    6.00    --  112.00  45.00 -60.00   43
 51  \w     37.00  70.00   1.00    6.00    --  112.00 -95.00  30.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1064992000
_diffrn_orient_matrix_UB_12      0.0316964000
_diffrn_orient_matrix_UB_13      0.0384397000
_diffrn_orient_matrix_UB_21      0.0947148000
_diffrn_orient_matrix_UB_22      -0.0153076000
_diffrn_orient_matrix_UB_23      0.0643043000
_diffrn_orient_matrix_UB_31      0.0196037000
_diffrn_orient_matrix_UB_32      0.2466382000
_diffrn_orient_matrix_UB_33      -0.0009241000
_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  0.0300
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26495
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.389
_diffrn_reflns_theta_min         4.128
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.513
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0528P)^2^+0.3485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2722
_reflns_number_total             2906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra02279b2.cif
_cod_data_source_block           anna_ros576_1
_cod_database_code               7242739
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 98.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C7(H7), C8(H8), C13(H13), C9(H9), C17(H17), C15(H15),
 C14(H14), C16(H16)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              79473
_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 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.634