TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF3-allyl alcohols with arenes into CF3-indanes
Zerov, Aleksey V.; Bulova, Anastasia A.; Khoroshilova, Olesya V.; Vasilyev, Aleksander V.; Organic Chemistry Frontiers 6 (2019) 3264–; doi:10.1039/C9QO00822E

data_1555068
_publ_section_title
;
 TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF3-allyl
 alcohols with arenes into CF3-indanes
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3264
_journal_paper_doi               10.1039/C9QO00822E
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C24 H21 F3'
_chemical_formula_sum            'C24 H21 F3'
_chemical_formula_weight         366.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                70.184(2)
_cell_angle_beta                 86.437(2)
_cell_angle_gamma                76.947(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9463(3)
_cell_length_b                   10.2875(3)
_cell_length_c                   11.0964(3)
_cell_measurement_reflns_used    8382
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.3960
_cell_measurement_theta_min      4.1860
_cell_volume                     935.84(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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    -17.00  28.00   0.50    0.23    --   41.22 -99.00-107.00   90
  2  \w     36.00  69.00   0.50    0.23    --   41.22 -99.00-107.00   66
  3  \w     75.00 109.00   0.50    0.93    --  101.00 -99.00-107.00   68
  4  \w    110.00 153.00   0.50    0.93    --  101.00  99.00  -1.00   86
  5  \w    -22.00  13.00   0.50    0.23    --  -41.22  77.00 -30.00   70
  6  \w   -108.00 -36.00   0.50    0.23    --  -41.22 -21.00 -90.00  144
  7  \w     -8.00  18.00   0.50    0.23    --  -41.22  99.00  -1.00   52
  8  \w    -69.00 -26.00   0.50    0.23    --  -41.22 -11.00-180.00   86
  9  \w    -40.00 -14.00   0.50    0.23    --  -41.22  21.00-120.00   52
 10  \w    -88.00 -62.00   0.50    0.23    --  -41.22 138.00  90.00   52
 11  \w    -64.00 -18.00   0.50    0.23    --  -41.22 138.00   0.00   92
 12  \w    -91.00 -66.00   0.50    0.23    --  -41.22 138.00   0.00   50
 13  \w    -53.00 -20.00   0.50    0.23    --  -41.22 138.00  90.00   66
 14  \w    -46.00 -19.00   0.50    0.23    --  -41.22  65.00-120.00   54
 15  \w     -7.00  28.00   0.50    0.23    --  -41.22  21.00-120.00   70
 16  \w   -115.00 -73.00   0.50    0.23    --  -41.22 -11.00-180.00   84
 17  \w    -61.00 -36.00   0.50    0.23    --  -41.22  77.00 -30.00   50
 18  \w    -16.00  14.00   0.50    0.23    --   41.22 -77.00  60.00   60
 19  \w    -19.00  11.00   0.50    0.23    --   41.22 -65.00 120.00   60
 20  \w     42.00  67.00   0.50    0.23    --   41.22 -77.00  60.00   50
 21  \w    -13.00  55.00   0.50    0.23    --   41.22 -54.00 -60.00  136
 22  \w     74.00 100.00   0.50    0.23    --   41.22  65.00 -90.00   52
 23  \w     25.00  65.00   0.50    0.23    --   41.22  65.00 -90.00   80
 24  \w     16.00  48.00   0.50    0.23    --   41.22 -65.00 120.00   64
 25  \w     53.00 121.00   0.50    0.93    --  101.00 -77.00 -90.00  136
 26  \w     92.00 156.00   0.50    0.93    --  101.00  42.00-150.00  128
 27  \w     38.00  66.00   0.50    0.93    --  101.00 -59.00 150.00   56
 28  \w     86.00 156.00   0.50    0.93    --  101.00  50.00  60.00  140
 29  \w     89.00 126.00   0.50    0.93    --  101.00 -87.00 -60.00   74
 30  \w     47.00 124.00   0.50    0.93    --  101.00-133.00  90.00  154
 31  \w     83.00 125.00   0.50    0.93    --  101.00 111.00 -30.00   84
 32  \w    132.00 157.00   0.50    0.93    --  101.00 111.00 -30.00   50
 33  \w     58.00  84.00   0.50    0.93    --  101.00-133.00 150.00   52
 34  \w     76.00 110.00   0.50    0.93    --  101.00 -25.00 -90.00   68
 35  \w     61.00 116.00   0.50    0.93    --  101.00 -59.00  30.00  110
 36  \w     50.00 118.00   0.50    0.93    --  101.00 -59.00 -90.00  136
 37  \w     37.00 127.00   0.50    0.93    --  101.00 -87.00  60.00  180
 38  \w     81.00 110.00   0.50    0.93    --  101.00 -33.00-120.00   58
 39  \w     41.00  67.00   0.50    0.93    --  101.00 -33.00-120.00   52
 40  \w     95.00 147.00   0.50    0.93    --  101.00 111.00-120.00  104
 41  \w    112.00 145.00   0.50    0.93    --  101.00  68.00 150.00   66
 42  \w    106.00 151.00   0.50    0.93    --  101.00 111.00-150.00   90
 43  \w     75.00 113.00   0.50    0.93    --  101.00-111.00 150.00   76
 44  \w     94.00 130.00   0.50    0.93    --  101.00 -93.00-180.00   72
 45  \w    132.00 157.00   0.50    0.93    --  101.00  59.00-120.00   50
 46  \w    101.00 127.00   0.50    0.93    --  101.00  59.00-120.00   52
 47  \w     63.00  88.00   0.50    0.93    --  101.00 -93.00-180.00   50
 48  \w     81.00 106.00   0.50    0.93    --  101.00  68.00 150.00   50
 49  \w     92.00 156.00   0.50    0.93    --  101.00  93.00  30.00  128
 50  \w     34.00  69.00   0.50    0.93    --  101.00 -25.00 -90.00   70
 51  \w     97.00 149.00   0.50    0.93    --  101.00  68.00 120.00  104
 52  \w     45.00 115.00   0.50    0.93    --  101.00-111.00-120.00  140
 53  \w     34.00  59.00   0.50    0.93    --  101.00 -93.00-180.00   50
 54  \w     91.00 116.00   0.50    0.93    --  101.00-133.00 150.00   50
 55  \w     82.00 120.00   0.50    0.93    --  101.00 -59.00 150.00   76
 56  \w     95.00 121.00   0.50    0.93    --  101.00  42.00-180.00   52
 57  \w    100.00 125.00   0.50    0.93    --  101.00  42.00 -30.00   50
 58  \w     78.00 153.00   0.50    0.93    --  101.00  77.00 -90.00  150
 59  \w    107.00 133.00   0.50    0.93    --  101.00  99.00  -1.00   52
 60  \w    -35.00   0.00   0.50    0.23    --    4.00 109.00-136.05   70
 61  \w    -17.00   9.00   0.50    0.23    --   20.00 106.00 -13.24   52
 62  \w    -43.00 -18.00   0.50    0.23    --   24.00 153.00  58.15   50
 63  \w     -2.00  23.00   0.50    0.23    --   28.00  92.00-110.77   50
 64  \w      3.00  28.00   0.50    0.23    --   32.00  89.00   7.52   50
 65  \w      3.00  28.00   0.50    0.23    --   32.00  90.00 -49.88   50
 66  \w      9.00  34.00   0.50    0.23    --   36.00  84.00-179.91   50
 67  \w     15.00  40.00   0.50    0.23    --   40.00  80.00 -13.19   50
 68  \w     15.00  40.00   0.50    0.23    --   40.00  81.00 -76.75   50
 69  \w     19.00  44.00   0.50    0.23    --   44.00  81.00-159.25   50
 70  \w     19.00  44.00   0.50    0.23    --   44.00  79.00 -41.99   50
 71  \w     18.00  43.00   0.50    0.23    --   44.00  82.00 127.84   50
 72  \w     19.00  44.00   0.50    0.23    --   44.00  80.00 160.01   50
 73  \w     19.00  44.00   0.50    0.23    --   44.00  79.00 108.72   50
 74  \w     18.00  43.00   0.50    0.23    --   44.00  82.00  68.70   50
 75  \w     19.00  44.00   0.50    0.23    --   44.00  79.00  32.25   50
 76  \w     23.00  49.00   0.50    0.23    --   48.00  76.00 -99.05   52
 77  \w     35.00  61.00   0.50    0.23    --   52.00  64.00 -81.33   52
 78  \w     27.00  54.00   0.50    0.23    --   52.00  77.00 158.71   54
 79  \w     29.00  55.00   0.50    0.23    --   52.00  73.00  15.97   52
 80  \w     75.00 101.00   0.50    0.23    --   52.00  77.00 158.71   52
 81  \w     57.00  84.00   0.50    0.23    --   52.00  73.00  15.97   54
 82  \w     37.00  63.00   0.50    0.23    --   52.00  72.00 118.44   52
 83  \w     27.00  53.00   0.50    0.23    --   52.00  76.00 -18.11   52
 84  \w     29.00  55.00   0.50    0.23    --   52.00  76.00-152.86   52
 85  \w     31.00  61.00   0.50    0.23    --   56.00  76.00  65.51   60
 86  \w     46.00  86.00   0.50    0.23    --   60.00  62.00 161.37   80
 87  \w     39.00  69.00   0.50    0.23    --   64.00  77.00-145.35   60
 88  \w     42.00  68.00   0.50    0.23    --   64.00  74.00 -66.43   52
 89  \w     40.00  92.00   0.50    0.23    --   64.00  76.00  27.22  104
 90  \w     47.00  73.00   0.50    0.23    --   64.00  58.00 150.53   52
 91  \w     52.00  99.00   0.50    0.23    --   68.00  66.00 111.94   94
 92  \w     50.00  83.00   0.50    0.23    --   68.00  62.00 102.39   66
 93  \w     50.00  75.00   0.50    0.93    --   72.00  70.00-119.56   50
 94  \w     53.00 112.00   0.50    0.93    --   76.00  74.00 -15.64  118
 95  \w     59.00  86.00   0.50    0.93    --   76.00  61.00 -30.36   54
 96  \w    105.00 138.00   0.50    0.93    --   76.00  77.00  51.52   66
 97  \w     52.00 101.00   0.50    0.93    --   76.00  77.00  51.52   98
 98  \w     57.00  83.00   0.50    0.93    --   80.00  73.00 -67.68   52
 99  \w     64.00 115.00   0.50    0.93    --   84.00  67.00-104.32  102
100  \w     70.00  96.00   0.50    0.93    --   88.00  62.00 -89.70   52
101  \w     73.00  99.00   0.50    0.93    --   96.00  73.00 -68.93   52
102  \w    109.00 157.00   0.50    0.93    --  101.00 111.00 -90.00   96
103  \w     84.00 119.00   0.50    0.93    --  101.00  59.00  30.00   70
104  \w     83.00 136.00   0.50    0.93    --  101.00  59.00-180.00  106
105  \w    122.00 148.00   0.50    0.93    --  101.00  68.00   0.00   52
106  \w     72.00  98.00   0.50    0.93    --  101.00 -33.00  30.00   52
107  \w     36.00  62.00   0.50    0.93    --  101.00 -33.00  30.00   52
108  \w     81.00 110.00   0.50    0.93    --  101.00  68.00   0.00   58
109  \w     76.00 102.00   0.50    0.93    --  101.00  77.00 120.00   52
110  \w     78.00 105.00   0.50    0.93    --  101.00  77.00   0.00   54
111  \w     76.00 140.00   0.50    0.93    --  101.00  77.00 -30.00  128
112  \w     66.00 110.00   0.50    0.93    --  101.00 -33.00 -60.00   88
113  \w     77.00 123.00   0.50    0.93    --  101.00  77.00  84.38   92
114  \w    115.00 141.00   0.50    0.93    --  101.00  77.00 150.00   52
115  \w     77.00 102.00   0.50    0.93    --  101.00  77.00 150.00   50
116  \w    132.00 157.00   0.50    0.93    --  101.00  77.00  60.00   50
117  \w     78.00 103.00   0.50    0.93    --  101.00 -42.00-180.00   50
118  \w     77.00 127.00   0.50    0.93    --  101.00  77.00  60.00  100
119  \w    120.00 156.00   0.50    0.93    --  101.00  77.00 -60.00   72
120  \w    124.00 155.00   0.50    0.93    --  101.00  59.00  30.00   62
121  \w     71.00 107.00   0.50    0.93    --  101.00 -25.00  90.00   72
122  \w     77.00 151.00   0.50    0.93    --  101.00  77.00  90.00  148
123  \w     85.00 121.00   0.50    0.93    --  101.00  59.00 -90.00   72
124  \w    123.00 150.00   0.50    0.93    --  101.00  77.00-150.00   54
125  \w    132.00 157.00   0.50    0.93    --  101.00  77.00  30.00   50
126  \w     76.00 117.00   0.50    0.93    --  101.00  77.00-150.00   82
127  \w     78.00 105.00   0.50    0.93    --  101.00  77.00 -60.00   54
128  \w    124.00 150.00   0.50    0.93    --  101.00  77.00-180.00   52
129  \w     76.00 102.00   0.50    0.93    --  101.00  77.00  30.00   52
130  \w     76.00 102.00   0.50    0.93    --  101.00  77.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0611597000
_diffrn_orient_matrix_UB_12      -0.1308664000
_diffrn_orient_matrix_UB_13      0.0812643000
_diffrn_orient_matrix_UB_21      -0.0996670000
_diffrn_orient_matrix_UB_22      0.0155631000
_diffrn_orient_matrix_UB_23      -0.1144994000
_diffrn_orient_matrix_UB_31      0.1325935000
_diffrn_orient_matrix_UB_32      -0.0960935000
_diffrn_orient_matrix_UB_33      -0.0454875000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17525
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.028
_diffrn_reflns_theta_min         4.236
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
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    1.300
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.3791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1375
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3123
_reflns_number_total             3653
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00822e2.cif
_cod_data_source_block           7072-9926_b-9a
_cod_database_code               1555068
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.892
_shelx_estimated_absorpt_t_min   0.777
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C23(H23), C11(H11), C19(H19), C22(H22), C21(H21), C12(H12),
 C15(H15), C20(H20), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              41754
_shelx_hkl_checksum              73452
_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 4.384
_oxdiff_exptl_absorpt_empirical_full_min 0.814