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_7064312
_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         '0.09(C26 H23 N5 O3)'
_chemical_formula_sum            'C H N O'
_chemical_formula_weight         43.03
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-02
_audit_creation_method
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_audit_update_record
;
2025-09-07 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            43
_cell_length_a                   9.3410(2)
_cell_length_b                   12.3538(3)
_cell_length_c                   19.8410(5)
_cell_measurement_reflns_used    6481
_cell_measurement_temperature    304.6(2)
_cell_measurement_theta_max      25.9870
_cell_measurement_theta_min      2.0520
_cell_volume                     2289.59(9)
_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      304.6(2)
_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 0.961
_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    -69.00 -36.00   0.50    5.00    --  -14.97 125.00  90.00   66
  2  \w    -46.00 -21.00   0.50    5.00    --  -14.97 126.00 127.00   50
  3  \w    -38.00  58.00   0.50    5.00    --  -14.97  30.00  90.00  192
  4  \w     31.00  77.00   0.50    5.00    --   16.22  30.00  90.00   92
  5  \w     -7.00  18.00   0.50    5.00    --   16.22  30.00  90.00   50
  6  \w      9.00  60.00   0.50    5.00    --   16.22-121.00 137.00  102
  7  \w    -58.00 -13.00   0.50    5.00    --  -14.97 125.00 -60.00   90
  8  \w    -45.00 -10.00   0.50    5.00    --  -14.97 125.00 -90.00   70
  9  \w     13.00  48.00   0.50    5.00    --   16.22 -10.00-119.00   70
 10  \w    -49.00 -23.00   0.50    5.00    --   16.22 -10.00-119.00   52
;
_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      -0.0084840000
_diffrn_orient_matrix_UB_12      -0.0010016000
_diffrn_orient_matrix_UB_13      0.0355049000
_diffrn_orient_matrix_UB_21      0.0055369000
_diffrn_orient_matrix_UB_22      -0.0572620000
_diffrn_orient_matrix_UB_23      -0.0003279000
_diffrn_orient_matrix_UB_31      0.0752761000
_diffrn_orient_matrix_UB_32      0.0041212000
_diffrn_orient_matrix_UB_33      0.0040547000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12731
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_min         1.942
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59154
_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_density_diffrn    1.342
_exptl_crystal_F_000             946
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 1151 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0599
_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^)+(0.1106P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1825
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                3521
_reflns_number_total             4665
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03725e2.cif
_cod_data_source_block           extr17
_cod_database_code               7064312
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.67
_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) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N005(H00A,H00B)
2.b Ternary CH refined with riding coordinates:
 C00E(H00E), C00O(H00O)
2.c Secondary CH2 refined with riding coordinates:
 C00P(H00C,H00D), C00S(H00F,H00G), C00U(H00H,H00I), C00V(H00K,H00L)
2.d Aromatic/amide H refined with riding coordinates:
 N002(H002), C009(H009), C00J(H00J), C00M(H00M), C00Q(H00Q), C00R(H00R),
 C00T(H00T), C00X(H00X)
2.e Idealised Me refined as rotating group:
 C00W(H00N,H00P,H00S)
;
_shelx_res_checksum              68009
_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 1.394
_oxdiff_exptl_absorpt_empirical_full_min 0.699