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_7156226
_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         'C14 H14 F3 N O2'
_chemical_formula_sum            'C14 H14 F3 N O2'
_chemical_formula_weight         285.26
_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'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-02-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-02-08 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.7429(4)
_cell_length_b                   13.5554(6)
_cell_length_c                   21.9361(9)
_cell_measurement_reflns_used    7520
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.558
_cell_measurement_theta_min      3.260
_cell_volume                     2599.7(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      149.99
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10551
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        66.628
_diffrn_reflns_theta_max         66.628
_diffrn_reflns_theta_min         4.030
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.090
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1214 before and 0.0709 after correction. The Ratio of minimum to maximum transmission is 0.7731. 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    1.458
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0424P)^2^+1.1650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2113
_reflns_number_total             2237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00602d2.cif
_cod_data_source_block           20180103_zubing_c14ho2nf3_0m_a
_cod_depositor_comments
'Adding full bibliography for 7156224--7156226.cif.'
_cod_database_code               7156226
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C13(H13), C4(H4)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_shelx_res_checksum              5731
_olex2_submission_special_instructions 'No special instructions were received'