Organocatalyzed [4 + 2] cycloaddition of α,β-unsaturated ketones and isatylidene malononitrile: accessing spiro[3-arylcyclohexanone]oxindole derivatives
Patil, Baliram R.; Nichinde, Chandrakant B.; Chaudhari, Suryakant S.; Krishna, Gamidi Rama; Kinage, Anil K.; RSC Advances 14 (2024) 2873–2877; doi:10.1039/D3RA07652K

data_7248037
_publ_section_title
;
 Organocatalyzed [4 + 2] cycloaddition of \a,\b-unsaturated ketones and
 isatylidene malononitrile: accessing spiro[3-arylcyclohexanone]oxindole
 derivatives
;
_journal_issue                   5
_journal_name_full               'RSC Advances'
_journal_page_first              2873
_journal_page_last               2877
_journal_paper_doi               10.1039/D3RA07652K
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         '2(C22 H17 N3 O2), H2 O'
_chemical_formula_sum            'C44 H36 N6 O5'
_chemical_formula_weight         728.79
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-10-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-10-21 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.7011(14)
_cell_length_b                   15.7011(14)
_cell_length_c                   29.337(3)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.30
_cell_volume                     7232.3(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            39894
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.301
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4605
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1720 before and 0.0976 after correction.
The Ratio of minimum to maximum transmission is 0.6177.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       Block
_exptl_crystal_F_000             3056
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   0.7455
_exptl_transmission_factor_min   0.4605
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0286P)^2^+6.6492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3375
_reflns_number_total             3952
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra07652k2.cif
_cod_data_source_block           3Ac
_cod_original_cell_volume        7232.2(15)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7248037
_publcif_datablock.id            {95a42c3a-2835-4e50-9f85-4e4c8df87f00}
_shelx_shelxl_version_number     2018/3
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              30804
_shelx_hkl_checksum              59771
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;