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_7242738
_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         'C22 H17 Br N2 O, C6 H6'
_chemical_formula_sum            'C28 H23 Br N2 O'
_chemical_formula_weight         483.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-04-09 deposited with the CCDC.	2021-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                71.840(2)
_cell_angle_beta                 74.029(2)
_cell_angle_gamma                82.625(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8147(2)
_cell_length_b                   9.9723(2)
_cell_length_c                   14.5140(4)
_cell_measurement_reflns_used    12482
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9240
_cell_measurement_theta_min      4.6280
_cell_volume                     1164.21(5)
_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 0.997
_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    -84.00   5.00   1.00    4.00    --  -41.72 112.00 116.00   89
  2  \w     17.00  90.00   1.00    4.00    --   41.72-112.00  23.00   73
  3  \w     36.00 109.00   1.00   16.00    --  112.00-112.00  23.00   73
  4  \w    104.00 178.00   1.00   16.00    --  112.00 112.00 116.00   74
  5  \w   -116.00 -17.00   1.00    4.00    --  -41.72 -38.00 -30.00   99
  6  \w    -66.00  33.00   1.00    4.00    --  -41.72  38.00 150.00   99
  7  \w      9.00  42.00   1.00    4.00    --   41.72  78.00 -39.51   33
  8  \w      7.00  33.00   1.00    4.00    --   42.00  84.00   5.81   26
  9  \w     29.00 131.00   1.00    4.00    --   58.00  60.00-113.14  102
 10  \w     30.00 106.00   1.00   16.00    --  112.00 -95.00 -30.00   76
 11  \w    103.00 178.00   1.00   16.00    --  112.00  77.00  90.00   75
 12  \w     83.00 178.00   1.00   16.00    --  112.00  61.00-180.00   95
 13  \w     30.00 106.00   1.00   16.00    --  112.00 -95.00 150.00   76
 14  \w    104.00 178.00   1.00   16.00    --  112.00 111.00  30.00   74
 15  \w    103.00 178.00   1.00   16.00    --  112.00  77.00  60.00   75
 16  \w    104.00 178.00   1.00   16.00    --  112.00 111.00  90.00   74
 17  \w     61.00 146.00   1.00   16.00    --  112.00 178.00-180.00   85
 18  \w    104.00 178.00   1.00   16.00    --  112.00 111.00   0.00   74
 19  \w    103.00 178.00   1.00   16.00    --  112.00  77.00 150.00   75
 20  \w     36.00 109.00   1.00   16.00    --  112.00-111.00 150.00   73
 21  \w     36.00 109.00   1.00   16.00    --  112.00-111.00 -30.00   73
 22  \w     61.00 146.00   1.00   16.00    --  112.00 178.00 150.00   85
 23  \w     36.00 109.00   1.00   16.00    --  112.00-111.00-180.00   73
 24  \w     36.00 109.00   1.00   16.00    --  112.00-111.00   0.00   73
 25  \w     30.00 106.00   1.00   16.00    --  112.00 -95.00-180.00   76
 26  \w     30.00 106.00   1.00   16.00    --  112.00 -95.00-120.00   76
 27  \w     30.00 106.00   1.00   16.00    --  112.00 -95.00  60.00   76
 28  \w     36.00 109.00   1.00   16.00    --  112.00-111.00  60.00   73
 29  \w     86.00 178.00   1.00   16.00    --  112.00  45.00   0.00   92
 30  \w     30.00 106.00   1.00   16.00    --  112.00 -95.00  30.00   76
 31  \w     36.00 109.00   1.00   16.00    --  112.00-111.00 -60.00   73
 32  \w    104.00 178.00   1.00   16.00    --  112.00 111.00-180.00   74
 33  \w     83.00 178.00   1.00   16.00    --  112.00  61.00 -90.00   95
 34  \w     38.00 137.00   1.00   16.00    --  112.00 -39.00  44.67   99
 35  \w     36.00 145.00   1.00   16.00    --  112.00 -77.00  90.00  109
 36  \w     30.00 106.00   1.00   16.00    --  112.00 -95.00-150.00   76
 37  \w     36.00 109.00   1.00   16.00    --  112.00-111.00-120.00   73
 38  \w     39.00 138.00   1.00   16.00    --  112.00 -45.00  30.00   99
 39  \w     30.00 106.00   1.00   16.00    --  112.00 -95.00   0.00   76
 40  \w     84.00 178.00   1.00   16.00    --  112.00  30.00-180.00   94
 41  \w     83.00 178.00   1.00   16.00    --  112.00  61.00 120.00   95
 42  \w     39.00 138.00   1.00   16.00    --  112.00 -45.00-150.00   99
 43  \w     39.00 138.00   1.00   16.00    --  112.00 -45.00 120.00   99
 44  \w     30.00 147.00   1.00   16.00    --  112.00 -85.00  78.04  117
 45  \w     36.00 140.00   1.00   16.00    --  112.00 -30.00 150.00  104
 46  \w     16.00  42.00   1.00    4.00    --   50.00  82.00 128.41   26
 47  \w     16.00  42.00   1.00    4.00    --   50.00  82.00-165.77   26
 48  \w     29.00 131.00   1.00    4.00    --   58.00  59.00  87.06  102
 49  \w     38.00 145.00   1.00    4.00    --   70.00  73.00 146.11  107
;
_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      -0.0339916000
_diffrn_orient_matrix_UB_12      -0.1583001000
_diffrn_orient_matrix_UB_13      0.0390169000
_diffrn_orient_matrix_UB_21      -0.0719937000
_diffrn_orient_matrix_UB_22      0.0144304000
_diffrn_orient_matrix_UB_23      0.1061385000
_diffrn_orient_matrix_UB_31      -0.1636485000
_diffrn_orient_matrix_UB_32      0.0349753000
_diffrn_orient_matrix_UB_33      -0.0227871000
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29066
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.449
_diffrn_reflns_theta_min         3.309
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.574
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.919
_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    1.379
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+0.2397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4248
_reflns_number_total             4873
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra02279b2.cif
_cod_data_source_block           anna_1392_5
_cod_database_code               7242738
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.834
_shelx_estimated_absorpt_t_min   0.542
_reflns_odcompleteness_completeness 98.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Others
 Fixed Sof: C17(0.5) C27(0.5) H27(0.5) H14(0.5) C23(0.5) H23(0.5) C25(0.5)
 C26(0.5) H26(0.5) C24(0.5) H24(0.5) N2(0.5) H2A(0.5) H2B(0.5) N3(0.5) H3A(0.5)
 H3B(0.5) C22(0.5) H22(0.5) C28(0.5) C18(0.5) H18(0.5) C19(0.5) H19(0.5)
 C20(0.5) H20(0.5) C21(0.5) H21(0.5)
3.a Rotating group:
 N3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C6(H6), C7(H7), C12(H12), C9(H9), C27(H27), C16(H16),
 C13(H13), C14(H14), C23(H23), C15(H15), C26(H26), C24(H24), C30(H30), C31(H31),
  C32(H32), C33(H33), C34(H34), C29(H29), C22(H22), C18(H18), C19(H19),
 C20(H20), C21(H21)
3.c Fitted hexagon refined as free rotating group:
 C30(C31,C32,C33,C34,C29), C22(C28,C18,C19,C20,C21)
3.d X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_shelx_res_checksum              66535
_olex2_date_sample_data_collection 2021-02-13
_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 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.789