Solvent directed base-enabled diastereodivergent domino cycloaddition of isoxazole–oxindole styrenes and Michael additions of isoxazole–styrenes with vinyl malononitriles
Sathish, Kota; Majhi, Subir; Parida, Ankita; Nagaraju, Sakkani; Kashinath, Dhurke; New Journal of Chemistry 50 (2026) 2350–2355; doi:10.1039/D5NJ03725E

data_7064313
_publ_section_title
;
 Solvent directed base-enabled diastereodivergent domino cycloaddition of
 isoxazole--oxindole styrenes and Michael additions of isoxazole--styrenes
 with vinyl malononitriles
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2350
_journal_page_last               2355
_journal_paper_doi               10.1039/D5NJ03725E
_journal_volume                  50
_journal_year                    2026
_chemical_formula_moiety         'C25 H23 N5 O4'
_chemical_formula_sum            'C25 H23 N5 O4'
_chemical_formula_weight         457.48
_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
_audit_creation_date             2022-10-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2025-09-08 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                80.600(2)
_cell_angle_beta                 89.223(2)
_cell_angle_gamma                77.075(2)
_cell_formula_units_Z            4
_cell_length_a                   11.5473(3)
_cell_length_b                   13.9900(4)
_cell_length_c                   14.7675(3)
_cell_measurement_reflns_used    14666
_cell_measurement_temperature    304.9
_cell_measurement_theta_max      26.1320
_cell_measurement_theta_min      2.0750
_cell_volume                     2293.32(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      304.9
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.958
_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     12.00  54.00   0.50    5.36    --  -14.97   0.00  30.00   84
  2  \w     60.00  86.00   0.50    5.36    --   16.22  45.00  90.00   52
  3  \w     -5.00  52.00   0.50    5.36    --   16.22  45.00   0.00  114
  4  \w     48.00  87.00   0.50    5.36    --   16.22  30.00 -30.00   78
  5  \w     -7.00  41.00   0.50    5.36    --   16.22  30.00 -30.00   96
  6  \w    -14.00  22.00   0.50    5.36    --  -14.97 -94.00 -60.00   72
  7  \w    -26.00   8.00   0.50    5.36    --  -14.97 -94.00 -90.00   68
  8  \w     22.00  47.00   0.50    5.36    --   16.22-135.00-125.00   50
  9  \w    -36.00  10.00   0.50    5.36    --  -14.97 -94.00-150.00   92
 10  \w    -85.00   8.00   0.50    5.36    --  -14.97 -61.00-150.00  186
 11  \w    -39.00  55.00   0.50    5.36    --  -14.97  45.00-180.00  188
 12  \w     40.00  86.00   0.50    5.36    --   16.22  45.00-150.00   92
 13  \w     -8.00  27.00   0.50    5.36    --   16.22  45.00-150.00   70
 14  \w    -66.00 -22.00   0.50    5.36    --  -14.97 125.00-120.00   88
 15  \w    -71.00 -16.00   0.50    5.36    --  -14.97 135.00 -59.00  110
 16  \w    -31.00  -5.00   0.50    5.36    --  -14.97 -77.00  60.00   52
 17  \w    -30.00  16.00   0.50    5.36    --  -14.97 -94.00  30.00   92
 18  \w     20.00  47.00   0.50    5.36    --   16.22-134.00  53.00   54
 19  \w     -6.00  19.00   0.50    5.36    --  -14.97 -94.00 120.00   50
 20  \w    -60.00 -14.00   0.50    5.36    --  -14.97   0.00  30.00   92
 21  \w    -79.00 -19.00   0.50    5.36    --  -14.97 -61.00  60.00  120
 22  \w    -75.00  -2.00   0.50    5.36    --  -14.97 -45.00  90.00  146
 23  \w    -87.00 -46.00   0.50    5.36    --  -14.97 -77.00  60.00   82
 24  \w    -91.00 -66.00   0.50    5.36    --  -14.97   0.00  30.00   50
 25  \w    -66.00 -11.00   0.50    5.36    --  -14.97 125.00  90.00  110
 26  \w    -68.00 -41.00   0.50    5.36    --  -14.97 134.00 121.00   54
 27  \w    -58.00 -13.00   0.50    5.36    --  -14.97 125.00  30.00   90
 28  \w    -88.00   9.00   0.50    5.36    --  -14.97 -30.00 -60.00  194
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0113935000
_diffrn_orient_matrix_UB_12      0.0523018000
_diffrn_orient_matrix_UB_13      -0.0021722000
_diffrn_orient_matrix_UB_21      -0.0011604000
_diffrn_orient_matrix_UB_22      0.0063537000
_diffrn_orient_matrix_UB_23      -0.0486501000
_diffrn_orient_matrix_UB_31      -0.0619913000
_diffrn_orient_matrix_UB_32      0.0023078000
_diffrn_orient_matrix_UB_33      0.0001265000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            39514
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.970
_diffrn_reflns_theta_min         2.083
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         9568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0904P)^2^+0.1031P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6036
_reflns_number_total             9568
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03725e2.cif
_cod_data_source_block           extr18
_cod_database_code               7064313
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C29(H29), C5(H5), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C46(H46A,H46B), C31(H31A,H31B), C32(H32A,H32B), C6(H6A,H6B),
 C33(H33A,H33B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C44(H44), C41(H41), C43(H43), C42(H42), C18(H18), C16(H16),
 C22(H22), C17(H17), C9(H9), C34(H34), C47(H47)
2.d X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C49(H49A,H49B,H49C)
;
_shelx_res_checksum              18049
_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 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.628