Stereoselective synthesis of trifluoroethyl 3,2'-spirooxindole γ-lactam through the organocatalytic cascade reaction of 3-((2,2,2-trifluoroethyl)amino)indolin-2-one.
Liu, Shuai-Jiang; Mao, Qing; Zhan, Gu; Qin, Rui; Chen, Ben-Hong; Xue, Jing; Luo, Meng-Lan; Zhao, Qian; Han, Bo; Organic & biomolecular chemistry 19 (2021) 467–475; doi:10.1039/d0ob02166k

data_7157806
_publ_section_title
;
 Stereoselective synthesis of trifluoroethyl 3,2'-spirooxindole \g-lactam
 through the organocatalytic cascade reaction of
 3-((2,2,2-trifluoroethyl)amino)indolin-2-one.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              467
_journal_page_last               475
_journal_paper_doi               10.1039/d0ob02166k
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H20 Cl F3 N2 O2'
_chemical_formula_sum            'C26 H20 Cl F3 N2 O2'
_chemical_formula_weight         484.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-24 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.993(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1617(4)
_cell_length_b                   24.6313(11)
_cell_length_c                   11.5178(7)
_cell_measurement_reflns_used    2740
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8360
_cell_measurement_theta_min      3.6290
_cell_volume                     2314.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details
;
  1 omega  -13.00   13.00   1.0000    3.7500
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -99.0000 -150.0000 26

  2 omega  -12.00   88.00   1.0000    3.7500
omega____ theta____ kappa____ phi______ frames
    -       17.6648   19.0000  -60.0000 100

  3 omega    3.00   87.00   1.0000    3.7500
omega____ theta____ kappa____ phi______ frames
    -       17.6648   38.0000    0.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0129223000
_diffrn_orient_matrix_UB_12      0.0094782000
_diffrn_orient_matrix_UB_13      -0.0577496000
_diffrn_orient_matrix_UB_21      0.0842015000
_diffrn_orient_matrix_UB_22      0.0068463000
_diffrn_orient_matrix_UB_23      -0.0022510000
_diffrn_orient_matrix_UB_31      0.0172997000
_diffrn_orient_matrix_UB_32      -0.0263419000
_diffrn_orient_matrix_UB_33      -0.0213010000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10939
_diffrn_reflns_point_group_measured_fraction_full 0.746
_diffrn_reflns_point_group_measured_fraction_max 0.591
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.410
_diffrn_reflns_theta_min         2.995
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1392 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         7552
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0579P)^2^+0.0296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.385
_reflns_Friedel_fraction_full    0.482
_reflns_Friedel_fraction_max     0.336
_reflns_number_gt                5383
_reflns_number_total             7552
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02166k2.cif
_cod_data_source_block           200715_s1_mj
_cod_depositor_comments          'Adding full bibliography for 7157806.cif.'
_cod_database_code               7157806
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3cl1
_reflns_odcompleteness_completeness 99.77
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C18(H18A,H18B), C20(H20A,H20B), C36(H36A,H36B), C44(H44A,
 H44B), C46(H46A,H46B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C14(H14), C16(H16), C17(H17),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C30(H30), C31(H31), C32(H32),
  C33(H33), C39(H39), C40(H40), C42(H42), C43(H43), C48(H48), C49(H49),
 C50(H50), C51(H51), C52(H52)
;
_shelx_res_checksum              21770
_olex2_submission_special_instructions 'No special instructions were received'