Convenient synthesis of spiro-pyrazolone–pyrrolidinones via ipso-cyclization of arylidene pyrazolones with 2-chloro-N-phenylacetamides
Gond, Kavyashree Kuppayya; Maddani, Mahagundappa Rachappa; New Journal of Chemistry 48 (2024) 15866–15869; doi:10.1039/D4NJ02670E

data_7063426
_publ_section_title
;
 Convenient synthesis of spiro-pyrazolone--pyrrolidinones via
 ipso-cyclization of arylidene pyrazolones with
 2-chloro-N-phenylacetamides
;
_journal_issue                   36
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15866
_journal_page_last               15869
_journal_paper_doi               10.1039/D4NJ02670E
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C25 H19 Cl2 N3 O2'
_chemical_formula_sum            'C25 H19 Cl2 N3 O2'
_chemical_formula_weight         464.33
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-06-09 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.0860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.15780(10)
_cell_length_b                   7.97410(10)
_cell_length_c                   20.9819(2)
_cell_measurement_reflns_used    13797
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.6700
_cell_measurement_theta_min      3.3480
_cell_volume                     2201.06(4)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_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     14.00 110.00   0.50    0.20    --   40.83  77.00 150.00  192
  2  \w     14.00 110.00   0.50    0.20    --   40.83  77.00  90.00  192
  3  \w     87.00 171.00   0.50    0.38    --  104.00  42.00  30.00  168
  4  \w     82.00 172.00   0.50    0.38    --  104.00  59.00  60.00  180
  5  \w     22.00 113.00   0.50    0.20    --   40.83  20.00   3.00  182
  6  \w     79.00 177.00   0.50    0.38    --  104.00  17.00 -60.00  196
  7  \w     85.00 176.00   0.50    0.38    --  104.00  20.00   3.00  182
  8  \w     90.00 172.00   0.50    0.38    --  104.00  33.00 -30.00  164
  9  \w    102.00 170.00   0.50    0.38    --  104.00 111.00-150.00  136
 10  \w    102.00 170.00   0.50    0.38    --  104.00 111.00-180.00  136
 11  \w     89.00 170.00   0.50    0.38    --  104.00 133.00 150.00  162
 12  \w     38.00 118.00   0.50    0.38    --  104.00-133.00  60.00  160
 13  \w     38.00 108.00   0.50    0.38    --  104.00-111.00 120.00  140
 14  \w     38.00 108.00   0.50    0.38    --  104.00-111.00  90.00  140
 15  \w     38.00 108.00   0.50    0.38    --  104.00-111.00  60.00  140
 16  \w     18.00  78.00   0.50    0.20    --   40.83-104.00 -60.00  120
 17  \w     41.00 100.00   0.50    0.20    --   40.83-138.00-180.00  118
 18  \w     32.00 106.00   0.50    0.38    --  104.00 -93.00   0.00  148
 19  \w     35.00 105.00   0.50    0.38    --  104.00 -77.00  60.00  140
 20  \w     36.00  83.00   0.50    0.38    --  104.00 -68.00 120.00   94
 21  \w     36.00  83.00   0.50    0.38    --  104.00 -68.00  60.00   94
 22  \w     36.00  68.00   0.50    0.38    --  104.00 -59.00 -60.00   64
 23  \w     36.00  83.00   0.50    0.38    --  104.00 -68.00 -60.00   94
 24  \w     36.00  68.00   0.50    0.38    --  104.00 -59.00 -90.00   64
 25  \w     36.00  83.00   0.50    0.38    --  104.00 -68.00 -90.00   94
 26  \w     36.00  83.00   0.50    0.38    --  104.00 -68.00-120.00   94
 27  \w     36.00  68.00   0.50    0.38    --  104.00 -59.00-150.00   64
 28  \w     36.00  68.00   0.50    0.38    --  104.00 -59.00-180.00   64
 29  \w     36.00  68.00   0.50    0.38    --  104.00 -59.00-120.00   64
 30  \w     36.00  68.00   0.50    0.38    --  104.00 -59.00  90.00   64
 31  \w     36.00  68.00   0.50    0.38    --  104.00 -59.00 150.00   64
 32  \w    -25.00  48.00   0.50    0.20    --   40.83 -43.00 150.00  146
 33  \w    -27.00  37.00   0.50    0.20    --   40.83 -32.00  90.00  128
 34  \w    -35.00  24.00   0.50    0.20    --   40.83 -11.00-180.00  118
 35  \w    -31.00  27.00   0.50    0.20    --   40.83 -20.00-163.00  116
 36  \w   -155.00 -64.00   0.50    0.38    --  -82.50 -20.00-163.00  182
 37  \w    -47.00 -15.00   0.50    0.38    --  -82.50  42.00-120.00   64
 38  \w    -47.00 -15.00   0.50    0.38    --  -82.50  42.00 -30.00   64
 39  \w    -47.00 -15.00   0.50    0.38    --  -82.50  42.00   0.00   64
 40  \w    -24.00  35.00   0.50    0.20    --  -40.83  11.00  90.00  118
 41  \w    -37.00  27.00   0.50    0.20    --  -40.83  32.00 120.00  128
 42  \w    -24.00  35.00   0.50    0.20    --  -40.83  11.00   0.00  118
 43  \w    -27.00  31.00   0.50    0.20    --  -40.83  20.00   3.00  116
 44  \w    -80.00 -10.00   0.50    0.38    --  -82.50  93.00  60.00  140
 45  \w   -108.00 -21.00   0.50    0.20    --  -40.83 -54.00  30.00  174
 46  \w   -108.00 -21.00   0.50    0.20    --  -40.83 -54.00 120.00  174
 47  \w   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00 -30.00  190
 48  \w   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00 -90.00  190
 49  \w   -108.00 -21.00   0.50    0.20    --  -40.83 -54.00-180.00  174
 50  \w   -113.00 -22.00   0.50    0.20    --  -40.83 -20.00-163.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0207516000
_diffrn_orient_matrix_UB_12      -0.0089358000
_diffrn_orient_matrix_UB_13      0.0719182000
_diffrn_orient_matrix_UB_21      0.1111700000
_diffrn_orient_matrix_UB_22      0.0498397000
_diffrn_orient_matrix_UB_23      0.0147565000
_diffrn_orient_matrix_UB_31      -0.0306412000
_diffrn_orient_matrix_UB_32      0.1863839000
_diffrn_orient_matrix_UB_33      -0.0004923000
_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  0.0306
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24013
_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         72.046
_diffrn_reflns_theta_min         3.360
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.884
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89786
_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_density_diffrn    1.401
_exptl_crystal_F_000             960
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0430P)^2^+0.5903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3749
_reflns_number_total             4321
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02670e2.cif
_cod_data_source_block           kg-384_autored
_cod_depositor_comments          'Adding full bibliography for 7063426.cif.'
_cod_database_code               7063426
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C H Cl N O'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C18(H18), C1(H1), C16(H16), C21(H21), C5(H5), C17(H17), C23(H23),
 C24(H24), C22(H22), C2(H2), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              82699
_shelx_hkl_checksum              92981
_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 1.151
_oxdiff_exptl_absorpt_empirical_full_min 0.862