Synthesis of CF<sub>3</sub>-containing spiro-epoxyoxindoles via the Corey-Chaykovsky reaction of N-alkyl isatins with Ph<sub>2</sub>S<sup>+</sup>CH<sub>2</sub>CF<sub>3</sub>OTf<sup/>.
Cheng, Bin; Zu, Bing; Li, Yuntong; Tao, Cheng; Zhang, Chen; Wang, Renqi; Li, Yun; Zhai, Hongbin; Organic & biomolecular chemistry 16 (2018) 3564–3567; doi:10.1039/c8ob00602d

data_7156224
_publ_section_title
;
 Synthesis of CF<sub>3</sub>-containing spiro-epoxyoxindoles via the
 Corey-Chaykovsky reaction of N-alkyl isatins with
 Ph<sub>2</sub>S<sup>+</sup>CH<sub>2</sub>CF<sub>3</sub>OTf&lt;sup/&gt;.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3564
_journal_page_last               3567
_journal_paper_doi               10.1039/c8ob00602d
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C H2 Cl2, C25 H20 F3 N O2'
_chemical_formula_sum            'C26 H22 Cl2 F3 N O2'
_chemical_formula_weight         508.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-01-19 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                81.577(2)
_cell_angle_beta                 80.9200(10)
_cell_angle_gamma                72.3840(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3021(9)
_cell_length_b                   11.1033(11)
_cell_length_c                   11.8279(11)
_cell_measurement_reflns_used    4883
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.00
_cell_measurement_theta_min      2.47
_cell_volume                     1143.41(19)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6309
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         1.753
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0730 before and 0.0335 after correction. The Ratio of minimum to maximum transmission is 0.8665. The \l/2 correction factor is 0.0015.'
_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    1.477
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0703P)^2^+1.0156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3934
_reflns_number_total             4441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00602d2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7156224--7156226.cif.'
_cod_database_code               7156224
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: Cl1(0.75) C26(0.5) H26A(0.5) H26B(0.5) Cl1'(0.25) C26'(0.5)
 H26C(0.5) H26D(0.5)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C2(H2A,H2B), C19(H19A,H19B), C26'(H26C,H26D)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_shelx_res_checksum              86033
_olex2_submission_special_instructions 'No special instructions were received'