Constructing spirooxindoles from non-oxindole precursors: a one-pot nitro-reduction/double lactamization approach to spiro[indoline-3,3'-quinoline]-2,2'-diones.
Chouhan, Raju; Gogoi, Abhijit; Das, Sajal Kumar; Organic & biomolecular chemistry 22 (2024) 7601–7606; doi:10.1039/d4ob01178c

data_7160101
_publ_section_title
;
 Constructing spirooxindoles from non-oxindole precursors: a one-pot
 nitro-reduction/double lactamization approach to
 spiro[indoline-3,3'-quinoline]-2,2'-diones.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7601
_journal_page_last               7606
_journal_paper_doi               10.1039/d4ob01178c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C22 H20 F N O2'
_chemical_formula_sum            'C22 H20 F N O2'
_chemical_formula_weight         349.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-05-05
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-05 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.320(2)
_cell_length_b                   13.450(3)
_cell_length_c                   26.043(5)
_cell_measurement_reflns_used    2039
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      16.05
_cell_measurement_theta_min      2.52
_cell_volume                     3614.9(13)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2391
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            122785
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.341
_diffrn_reflns_theta_min         1.564
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5384
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1441 before and 0.0842 after correction.
The Ratio of minimum to maximum transmission is 0.7220.
The \l/2 correction factor is Not present.
;
_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    1.284
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_preparation
'Slow evaporation from a solution of 10% ethyl acetate in hexanes'
_exptl_crystal_recrystallization_method
'Slow evaporation from a solution of 10% ethyl acetate in hexanes'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0154(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.0666
_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^)+(0.0891P)^2^+0.8605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.2011
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1591
_reflns_number_total             3307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01178c2.cif
_cod_data_source_block           skn_a
_cod_depositor_comments          'Adding full bibliography for 7160101.cif.'
_cod_database_code               7160101
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H01D(0.6) H01F(0.6) H01G(0.4) H01H(0.4) H02A(0.6) H02B(0.6)
 H02C(0.4) H02D(0.4) C02W(0.6) H02K(0.6) H02L(0.6) C1(0.4) H1A(0.4) H1B(0.4)
3.a Secondary CH2 refined with riding coordinates:
 C01X(H01D,H01F), C01X(H01G,H01H), C025(H02A,H02B), C025(H02C,H02D), C02W(H02K,
 H02L), C1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C01E(H01E), C01J(H01J), C01R(H01R), C026(H026), C02C(H02E), C02F(H02F),
 C02J(H02J), C02N(H02N)
3.c Idealised Me refined as rotating group:
 C01O(H01A,H01B,H01C), C02M(H02G,H02H,H02I)
;
_shelx_res_checksum              81571
_olex2_submission_special_instructions 'No special instructions were received'