Metal-Free Visible-Light-Promoted Trifluoromethylation of Vinylcyclopropanes Using Pyrylium Salt as a Photoredox Catalyst.
Chandu, Palasetty; Ghosh, Krishna Gopal; Sureshkumar, Devarajulu; The Journal of organic chemistry 84 (2019) 8771–8781; doi:10.1021/acs.joc.9b01033

data_4034149
_publ_section_title
;
 Metal-Free Visible-Light-Promoted Trifluoromethylation of
 Vinylcyclopropanes Using Pyrylium Salt as a Photoredox Catalyst.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8771
_journal_page_last               8781
_journal_paper_doi               10.1021/acs.joc.9b01033
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H17 F3 O4 S2'
_chemical_formula_sum            'C18 H17 F3 O4 S2'
_chemical_formula_weight         418.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9214(3)
_cell_length_b                   12.1231(4)
_cell_length_c                   13.9512(4)
_cell_measurement_reflns_used    12027
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      25.1200
_cell_measurement_theta_min      2.1980
_cell_volume                     1847.16(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -57.00  114.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -       26.7184   19.0000  150.0000 171

  2 omega   35.00  121.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -       26.7184  178.0000    0.0000 86

  3 omega  -20.00   32.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      -23.5000  -99.0000  120.0000 52

  4 omega  -20.00   32.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      -23.5000  -99.0000  -60.0000 52

  5 omega  -61.00   52.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      -23.5000   57.0000   30.0000 113

  6 omega  -49.00   65.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -       26.7184  -57.0000  120.0000 114

  7 omega   43.00  119.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -       26.7184  169.0000  152.0000 76

  8 omega  -11.00  103.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -       26.7184   57.0000  -90.0000 114

  9 omega  -99.00  -13.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      -23.5000  -57.0000  -30.0000 86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0156727000
_diffrn_orient_matrix_UB_12      0.0465965000
_diffrn_orient_matrix_UB_13      0.0281877000
_diffrn_orient_matrix_UB_21      -0.0365468000
_diffrn_orient_matrix_UB_22      -0.0339415000
_diffrn_orient_matrix_UB_23      0.0299594000
_diffrn_orient_matrix_UB_31      0.0513333000
_diffrn_orient_matrix_UB_32      -0.0098800000
_diffrn_orient_matrix_UB_33      0.0299248000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19504
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.23
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3267
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.4514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                3222
_reflns_number_total             3267
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b01033_si_002.cif
_cod_data_source_block           vcpfc_1
_cod_original_cell_volume        1847.16(9)
_cod_database_code               4034149
_chemical_oxdiff_formula         'C H O S F'
_reflns_odcompleteness_completeness 93.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H14(0.025) H6(0.02) H12(0.028) H8(0.026) H18(0.028) H10(0.034)
 H9(0.033) H5A(0.028) H5B(0.028) H17(0.039) H2A(0.038) H2B(0.038) H4(0.031)
 H15(0.033) H3(0.033) H11(0.035) H16(0.038)
 Fixed X: H14(0.6466) H6(0.5485) H12(0.564) H8(0.3185) H18(0.2988) H10(0.5778)
 H9(0.4109) H5A(0.5309) H5B(0.5426) H17(0.3507) H2A(0.1999) H2B(0.2871)
 H4(0.3136) H15(0.6947) H3(0.4316) H11(0.6542) H16(0.5479)
 Fixed Y: H14(0.8441) H6(0.7791) H12(0.5466) H8(0.6143) H18(0.9009)
 H10(0.3841) H9(0.4841) H5A(0.7864) H5B(0.9082) H17(0.8637) H2A(0.9179)
 H2B(0.9398) H4(0.9104) H15(0.7989) H3(0.8136) H11(0.4163) H16(0.8127)
 Fixed Z: H14(0.0842) H6(0.2321) H12(0.2201) H8(0.4285) H18(0.003) H10(0.4698)
 H9(0.5259) H5A(0.3918) H5B(0.3565) H17(-0.154) H2A(0.5247) H2B(0.6119)
 H4(0.3827) H15(-0.0734) H3(0.5359) H11(0.3187) H16(-0.1923)
;
_olex2_date_sample_data_collection 2018-05-14
_olex2_submission_special_instructions 'No special instructions were received'