Thioether-functionalized trifluoromethyl-alkynes, 1,3-dienes and allenes: divergent synthesis from reaction of 2-trifluoromethyl-1,3-conjugated enynes with sulfur nucleophiles
Cheng, Huayu; Zhou, Xiaofan; Hu, Anjing; Ding, Shiteng; Wang, Yimo; Xiao, Yuanjing; Zhang, Junliang; RSC Advances 8 (2018) 34088–; doi:10.1039/C8RA07834C

data_7231609
_publ_section_title
;
 Thioether-functionalized trifluoromethyl-alkynes, 1,3-dienes and allenes:
 divergent synthesis from reaction of 2-trifluoromethyl-1,3-conjugated
 enynes with sulfur nucleophiles
;
_journal_issue                   59
_journal_name_full               'RSC Advances'
_journal_page_first              34088
_journal_paper_doi               10.1039/C8RA07834C
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C17 H12 F3 N O2 S'
_chemical_formula_sum            'C17 H12 F3 N O2 S'
_chemical_formula_weight         351.34
_chemical_melting_point          326
_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     dual
_audit_creation_date             2018-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-13 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.3940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.09320(10)
_cell_length_b                   16.40420(10)
_cell_length_c                   15.81510(10)
_cell_measurement_reflns_used    24614
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2880
_cell_measurement_theta_min      3.9140
_cell_volume                     1554.84(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_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    -31.00  64.00   1.00    1.00    --    0.00  82.00 120.00   95
  2  \w    -19.00  89.00   1.00    1.00    --    0.00  38.00-180.00  108
  3  \w      9.00  80.00   1.00    1.00    --    0.00  82.00  60.00   71
  4  \w    -32.00  65.00   1.00    1.00    --    0.00  82.00 -30.00   97
  5  \w    -23.00  15.00   1.00    1.00    --    0.00  19.00 -30.00   38
  6  \w    -27.00   2.00   1.00    1.00    --    0.00  82.00  60.00   29
  7  \w     26.00  85.00   1.00    1.00    --    0.00  38.00-120.00   59
  8  \w    -17.00  23.00   1.00    1.00    --    0.00  38.00-120.00   40
  9  \w    -19.00  69.00   1.00    1.00    --    0.00  38.00  60.00   88
 10  \w     30.00  80.00   1.00    1.00    --    0.00  19.00 -30.00   50
 11  \w    113.00 184.00   1.00    1.00    --   95.80  81.00 -99.20   71
 12  \w    121.00 146.00   1.00    1.00    --   95.80  71.00  -4.32   25
 13  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  38.90   25
 14  \w     66.00 179.00   1.00    1.00    --   95.80  76.00 137.93  113
 15  \w     67.00  94.00   1.00    1.00    --   95.80  71.00  -4.32   27
 16  \w     63.00 108.00   1.00    1.00    --   95.80  81.00 -99.20   45
 17  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  24.28   26
 18  \w    130.00 162.00   1.00    1.00    --   95.80  73.00  84.23   32
 19  \w    103.00 185.00   1.00    1.00    --   95.80  61.00-180.00   82
 20  \w     71.00  97.00   1.00    1.00    --   95.80  61.00-180.00   26
 21  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 22  \w     41.00  76.00   1.00    1.00    --   95.80 -82.00-150.00   35
 23  \w     82.00 125.00   1.00    1.00    --   95.80 -82.00-150.00   43
 24  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -90.00   26
 25  \w     65.00 103.00   1.00    1.00    --   95.80  77.00   0.00   38
 26  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 27  \w     63.00 185.00   1.00    1.00    --   95.80  82.00   0.00  122
 28  \w     66.00  91.00   1.00    1.00    --   95.80  82.00 150.00   25
 29  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 -60.00   26
 30  \w     65.00  92.00   1.00    1.00    --   95.80  77.00 120.00   27
 31  \w     67.00 104.00   1.00    1.00    --   95.80  73.00  84.23   37
 32  \w     73.00 118.00   1.00    1.00    --   95.80  52.00 -97.03   45
 33  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 34  \w    113.00 185.00   1.00    1.00    --   95.80  82.00-120.00   72
 35  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 36  \w     61.00 120.00   1.00    1.00    --   95.80 -82.00  90.00   59
 37  \w    137.00 167.00   1.00    1.00    --   95.80  48.00-121.52   30
 38  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 39  \w     66.00 100.00   1.00    1.00    --   95.80  77.00 -30.00   34
 40  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  60.00   26
 41  \w      7.00 126.00   1.00    1.00    --   95.80 -82.00   0.00  119
 42  \w     65.00 137.00   1.00    1.00    --   95.80  77.00  90.00   72
 43  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 44  \w    102.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   83
 45  \w     75.00 124.00   1.00    1.00    --   95.80  45.00 150.00   49
 46  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 47  \w     75.00 118.00   1.00    1.00    --   95.80  45.00-150.00   43
 48  \w    123.00 149.00   1.00    1.00    --   95.80  45.00-150.00   26
 49  \w     65.00  96.00   1.00    1.00    --   95.80  77.00-150.00   31
 50  \w     65.00 113.00   1.00    1.00    --   95.80  77.00 150.00   48
 51  \w    100.00 126.00   1.00    1.00    --   95.80 -82.00 -60.00   26
 52  \w     77.00 181.00   1.00    1.00    --   95.80  45.00 -30.00  104
 53  \w     80.00 185.00   1.00    1.00    --   95.80  45.00  90.00  105
 54  \w     71.00 170.00   1.00    1.00    --   95.80  61.00  30.00   99
 55  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 56  \w     43.00 125.00   1.00    1.00    --   95.80 -82.00 150.00   82
 57  \w     16.00  68.00   1.00    1.00    --   95.80 -82.00 -60.00   52
 58  \w     74.00  99.00   1.00    1.00    --   95.80  48.00-121.52   25
 59  \w     16.00 123.00   1.00    1.00    --   95.80 -82.00 -90.00  107
 60  \w     72.00  98.00   1.00    1.00    --   95.80  61.00-150.00   26
 61  \w    116.00 180.00   1.00    1.00    --   95.80  61.00-150.00   64
 62  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 63  \w    147.00 172.00   1.00    1.00    --   95.80  77.00  24.28   25
 64  \w    152.00 184.00   1.00    1.00    --   95.80  79.00 -44.03   32
 65  \w     64.00  95.00   1.00    1.00    --   95.80  79.00 -44.03   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0331482000
_diffrn_orient_matrix_UB_12      -0.0708469000
_diffrn_orient_matrix_UB_13      0.0603400000
_diffrn_orient_matrix_UB_21      0.0464419000
_diffrn_orient_matrix_UB_22      0.0582353000
_diffrn_orient_matrix_UB_23      0.0776035000
_diffrn_orient_matrix_UB_31      -0.2507157000
_diffrn_orient_matrix_UB_32      0.0201630000
_diffrn_orient_matrix_UB_33      -0.0119619000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1193
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            37602
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.397
_diffrn_reflns_theta_min         3.916
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/DCM'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0032(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0599P)^2^+0.5834P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3026
_reflns_number_total             3160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra07834c2.cif
_cod_data_source_block           exp_479
_cod_database_code               7231609
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.636
_shelx_estimated_absorpt_t_min   0.410
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.b X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
;
_shelx_res_checksum              9870
_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 4.253
_oxdiff_exptl_absorpt_empirical_full_min 0.266