The Facile Synthesis of α-trifluoromethylthio Phosphonium Ylides with a Constrained Trifluoromethylthiooxide via Proton-transfer Procedure
Cao, Chengyao kimmy; Zhang, Yue; Lan, Tianlei; Liu, Wei; Chen, Chao; Chemical Communications  (2019) –; doi:10.1039/C9CC04234B

data_7123803
_publ_section_title
;
 The Facile Synthesis of \a-trifluoromethylthio Phosphonium Ylides with a
 Constrained Trifluoromethylthiooxide via Proton-transfer Procedure
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04234B
_journal_year                    2019
_chemical_formula_moiety         'C22 H18 F3 O2 P S'
_chemical_formula_sum            'C22 H18 F3 O2 P S'
_chemical_formula_weight         434.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-07 deposited with the CCDC.    2019-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.192(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7335(2)
_cell_length_b                   20.6854(3)
_cell_length_c                   10.7411(2)
_cell_measurement_reflns_used    6891
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.4010
_cell_measurement_theta_min      4.7270
_cell_volume                     2105.56(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -47.00 -16.00   1.00    1.00    --  -40.81 -57.00 -60.00   31
  2  \w    -61.00  31.00   1.00    1.00    --  -40.81  57.00  90.00   92
  3  \w     82.00 115.00   1.00    1.00    --   40.81  38.00-150.00   33
  4  \w     81.00 106.00   1.00    1.00    --  112.00  77.00 -30.00   25
  5  \w     87.00 171.00   1.00    1.00    --  112.00  61.00   0.00   84
  6  \w    132.00 175.00   1.00    1.00    --  112.00  77.00 -30.00   43
  7  \w    147.00 175.00   1.00    1.00    --  112.00  45.00-120.00   28
  8  \w     90.00 163.00   1.00    1.00    --  112.00  45.00 -30.00   73
  9  \w    130.00 166.00   1.00    1.00    --  112.00 111.00 120.00   36
 10  \w     88.00 177.00   1.00    1.00    --  112.00  45.00 -90.00   89
 11  \w     44.00 115.00   1.00    1.00    --  112.00-111.00 120.00   71
 12  \w     24.00  59.00   1.00    1.00    --   40.81-125.00 -30.00   35
 13  \w     30.00  75.00   1.00    1.00    --  112.00 -95.00 -90.00   45
 14  \w     37.00 107.00   1.00    1.00    --  112.00 -95.00 -60.00   70
 15  \w     38.00  71.00   1.00    1.00    --  112.00-111.00-180.00   33
 16  \w   -110.00 -64.00   1.00    1.00    --  -40.81 -57.00 -60.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0945245000
_diffrn_orient_matrix_UB_12      -0.0353447000
_diffrn_orient_matrix_UB_13      -0.1143398000
_diffrn_orient_matrix_UB_21      -0.1137954000
_diffrn_orient_matrix_UB_22      0.0525866000
_diffrn_orient_matrix_UB_23      -0.0079472000
_diffrn_orient_matrix_UB_31      0.0674337000
_diffrn_orient_matrix_UB_32      0.0391363000
_diffrn_orient_matrix_UB_33      -0.0925492000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10455
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.704
_diffrn_reflns_theta_min         4.275
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.459
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0404
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1407
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3997
_reflns_number_total             4378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04234b2.cif
_cod_data_source_block           20170307caochengyao1
_cod_database_code               7123803
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T)
2.b Idealised Me refined as rotating group:
 C00M(H00a,H00b,H00e)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.302
_oxdiff_exptl_absorpt_empirical_full_min 0.461