Trifluoromethyl-substituted sulfonium ylide: rh-catalyzed carbenoid addition to trifluoromethylthioether.
Liu, Yafei; Shao, Xinxin; Zhang, Panpan; Lu, Long; Shen, Qilong; Organic letters 17 (2015) 2752–2755; doi:10.1021/acs.orglett.5b01170

data_1519651
_publ_section_title
;
 Trifluoromethyl-substituted sulfonium ylide: rh-catalyzed carbenoid
 addition to trifluoromethylthioether.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2752
_journal_page_last               2755
_journal_paper_doi               10.1021/acs.orglett.5b01170
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C14 H15 F3 O4 S'
_chemical_formula_sum            'C14 H15 F3 O4 S'
_chemical_formula_weight         336.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.378(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4571(5)
_cell_length_b                   34.890(3)
_cell_length_c                   7.6271(7)
_cell_measurement_reflns_used    5762
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.43
_cell_measurement_theta_min      2.75
_cell_volume                     1443.2(2)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0256
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14482
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.573
_diffrn_reflns_theta_min         1.167
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0479 before and 0.0393 after correction.
The Ratio of minimum to maximum transmission is 0.9221.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0607P)^2^+0.8527P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3916
_reflns_number_total             4407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01170_si_002.cif
_cod_data_source_block           mo_dm14643_0m
_cod_depositor_comments          'Adding full bibliography for 1519651.cif.'
_cod_database_code               1519651
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.922
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              35609
_shelx_hkl_checksum              20010
_olex2_submission_special_instructions 'No special instructions were received'