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_1555072
_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         'C22 H16 Br F3'
_chemical_formula_sum            'C22 H16 Br F3'
_chemical_formula_weight         417.26
_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     iterative
_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                87.5911(16)
_cell_angle_beta                 80.5904(18)
_cell_angle_gamma                78.3143(18)
_cell_formula_units_Z            2
_cell_length_a                   9.02917(20)
_cell_length_b                   9.25385(19)
_cell_length_c                   11.1048(2)
_cell_measurement_reflns_used    9589
_cell_measurement_temperature    100(3)
_cell_measurement_theta_max      71.4980
_cell_measurement_theta_min      3.9720
_cell_volume                     896.36(3)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -108.00 -59.00   0.50    0.20    --  -41.35 -13.00-151.00   98
  2  \w    -24.00   7.00   0.50    0.20    --   41.35 -13.00-151.00   62
  3  \w     21.00  55.00   0.50    0.20    --   41.35 -13.00-151.00   68
  4  \w     68.00 113.00   0.50    0.20    --   41.35  13.00  20.00   90
  5  \w     45.00  91.00   0.50    0.20    --  101.00 -13.00-151.00   92
  6  \w     94.00 121.00   0.50    0.20    --  101.00  13.00  20.00   54
  7  \w     -7.00  31.00   0.50    0.20    --  -41.35  13.00  20.00   76
  8  \w    -53.00 -16.00   0.50    0.20    --  -41.35  13.00  20.00   74
  9  \w    -67.00 -19.00   0.50    0.20    --  -41.35  77.00  30.00   96
 10  \w     -3.00  22.00   0.50    0.20    --  -41.35  77.00  30.00   50
 11  \w     13.00  94.00   0.50    0.20    --   41.35-138.00-180.00  162
 12  \w     -8.00  27.00   0.50    0.20    --   41.35 -65.00-150.00   70
 13  \w     24.00  49.00   0.50    0.20    --   41.35 -32.00 120.00   50
 14  \w     46.00  72.00   0.50    0.20    --   41.35  32.00 -60.00   52
 15  \w     79.00 104.00   0.50    0.20    --   41.35  43.00 120.00   50
 16  \w     34.00  62.00   0.50    0.20    --   41.35 -65.00-150.00   56
 17  \w     74.00  99.00   0.50    0.20    --   41.35  32.00 120.00   50
 18  \w    -11.00  18.00   0.50    0.20    --   41.35 -32.00 120.00   58
 19  \w     32.00  90.00   0.50    0.20    --   41.35-138.00  90.00  116
 20  \w    -14.00  39.00   0.50    0.20    --   41.35 -32.00 -30.00  106
 21  \w     23.00  66.00   0.50    0.20    --   41.35-138.00-120.00   86
 22  \w     28.00  69.00   0.50    0.20    --   41.35  43.00 120.00   82
 23  \w     33.00  58.00   0.50    0.20    --   41.35 -54.00-180.00   50
 24  \w    -15.00  13.00   0.50    0.20    --   41.35 -54.00-180.00   56
 25  \w     76.00 123.00   0.50    0.20    --  101.00  77.00-120.00   94
 26  \w     44.00 117.00   0.50    0.20    --  101.00 -77.00  30.00  146
 27  \w     34.00 108.00   0.50    0.20    --  101.00 -25.00  60.00  148
 28  \w     86.00 111.00   0.50    0.20    --  101.00-111.00  30.00   50
 29  \w     36.00  62.00   0.50    0.20    --  101.00-111.00  30.00   52
 30  \w     42.00  98.00   0.50    0.20    --  101.00 -68.00-180.00  112
 31  \w     41.00 110.00   0.50    0.20    --  101.00 -33.00 120.00  138
 32  \w     39.00 123.00   0.50    0.20    --  101.00 -68.00 -90.00  168
 33  \w     39.00  65.00   0.50    0.20    --  101.00-133.00 150.00   52
 34  \w     97.00 154.00   0.50    0.20    --  101.00  59.00 120.00  114
 35  \w     74.00 105.00   0.50    0.20    --  101.00-111.00-120.00   62
 36  \w     81.00 131.00   0.50    0.20    --  101.00  93.00 -30.00  100
 37  \w     77.00 105.00   0.50    0.20    --  101.00 -42.00-120.00   56
 38  \w     88.00 157.00   0.50    0.20    --  101.00  42.00  30.00  138
 39  \w     51.00 104.00   0.50    0.20    --  101.00-111.00-180.00  106
 40  \w     45.00 110.00   0.50    0.20    --  101.00-111.00 -60.00  130
 41  \w     39.00  96.00   0.50    0.20    --  101.00 -68.00 120.00  114
 42  \w     94.00 143.00   0.50    0.20    --  101.00  33.00  90.00   98
 43  \w     83.00 129.00   0.50    0.20    --  101.00 -93.00 -60.00   92
 44  \w     99.00 127.00   0.50    0.20    --  101.00  93.00  30.00   56
 45  \w     36.00 105.00   0.50    0.20    --  101.00 -33.00-150.00  138
 46  \w     71.00 117.00   0.50    0.20    --  101.00 -50.00   0.00   92
 47  \w     39.00  73.00   0.50    0.20    --  101.00-133.00 -90.00   68
 48  \w    100.00 125.00   0.50    0.20    --  101.00  33.00   0.00   50
 49  \w    111.00 154.00   0.50    0.20    --  101.00  17.00 -90.00   86
 50  \w     83.00 137.00   0.50    0.20    --  101.00  68.00-180.00  108
 51  \w     48.00 105.00   0.50    0.20    --  101.00 -33.00 -30.00  114
 52  \w     64.00  89.00   0.50    0.20    --  101.00-111.00 150.00   50
 53  \w     95.00 124.00   0.50    0.20    --  101.00-133.00 150.00   58
 54  \w     16.00  42.00   0.50    0.20    --   41.35  77.00-150.00   52
 55  \w    -35.00 -10.00   0.50    0.20    --    8.00 116.00  52.26   50
 56  \w    -35.00 -10.00   0.50    0.20    --   16.00 129.00-112.05   50
 57  \w     -3.00  22.00   0.50    0.20    --   28.00  94.00-152.05   50
 58  \w     -3.00  22.00   0.50    0.20    --   28.00  96.00   7.76   50
 59  \w     -4.00  21.00   0.50    0.20    --   28.00  97.00 -49.33   50
 60  \w     -4.00  21.00   0.50    0.20    --   28.00  97.00 120.04   50
 61  \w      3.00  28.00   0.50    0.20    --   32.00  90.00-107.65   50
 62  \w      3.00  28.00   0.50    0.20    --   32.00  90.00  -7.52   50
 63  \w     15.00  40.00   0.50    0.20    --   40.00  81.00 102.37   50
 64  \w     14.00  39.00   0.50    0.20    --   40.00  82.00 155.86   50
 65  \w     19.00  44.00   0.50    0.20    --   44.00  78.00 -92.22   50
 66  \w     19.00  44.00   0.50    0.20    --   44.00  80.00 -71.15   50
 67  \w     19.00  44.00   0.50    0.20    --   44.00  79.00  44.91   50
 68  \w     18.00  43.00   0.50    0.20    --   44.00  82.00-142.93   50
 69  \w     19.00  44.00   0.50    0.20    --   44.00  81.00  61.67   50
 70  \w     18.00  43.00   0.50    0.20    --   44.00  82.00   7.64   50
 71  \w     92.00 117.00   0.50    0.20    --   52.00  77.00  55.07   50
 72  \w     32.00  78.00   0.50    0.20    --   52.00  77.00  55.07   92
 73  \w     28.00  54.00   0.50    0.20    --   52.00  76.00 159.26   52
 74  \w     28.00  53.00   0.50    0.20    --   52.00  77.00 119.76   50
 75  \w     31.00  78.00   0.50    0.20    --   56.00  77.00  25.29   94
 76  \w     79.00 105.00   0.50    0.20    --   56.00  73.00 -64.60   52
 77  \w     32.00  58.00   0.50    0.20    --   56.00  76.00 -39.28   52
 78  \w     92.00 118.00   0.50    0.20    --   56.00  76.00-114.64   52
 79  \w     35.00  61.00   0.50    0.20    --   56.00  76.00-114.64   52
 80  \w     31.00  72.00   0.50    0.20    --   56.00  76.00  91.66   82
 81  \w     34.00  60.00   0.50    0.20    --   56.00  75.00-160.17   52
 82  \w     34.00  65.00   0.50    0.20    --   56.00  73.00 -64.60   62
 83  \w     41.00  67.00   0.50    0.20    --   60.00  74.00-140.97   52
 84  \w    102.00 127.00   0.50    0.20    --   64.00  55.00 145.77   50
 85  \w     47.00  73.00   0.50    0.20    --   64.00  55.00 145.77   52
 86  \w     40.00  76.00   0.50    0.20    --   64.00  75.00 -17.86   72
 87  \w     45.00  87.00   0.50    0.20    --   64.00  68.00-179.44   84
 88  \w     57.00 110.00   0.50    0.20    --   72.00  53.00  32.21  106
 89  \w     47.00  76.00   0.50    0.20    --   72.00  77.00-163.95   58
 90  \w     59.00  85.00   0.50    0.20    --   76.00  62.00 -43.14   52
 91  \w     65.00  91.00   0.50    0.20    --   84.00  60.00 145.59   52
 92  \w    101.00 126.00   0.50    0.20    --   84.00  77.00-129.67   50
 93  \w     59.00  85.00   0.50    0.20    --   84.00  77.00-129.67   52
 94  \w     85.00 114.00   0.50    0.20    --  101.00  59.00  90.00   58
 95  \w     85.00 134.00   0.50    0.20    --  101.00  59.00 -90.00   98
 96  \w     81.00 107.00   0.50    0.20    --  101.00  68.00  30.00   52
 97  \w    121.00 154.00   0.50    0.20    --  101.00  77.00 120.00   66
 98  \w     78.00 114.00   0.50    0.20    --  101.00  77.00 120.00   72
 99  \w    107.00 133.00   0.50    0.20    --  101.00  77.00-180.00   52
100  \w    109.00 135.00   0.50    0.20    --  101.00  77.00 150.00   52
101  \w     76.00 102.00   0.50    0.20    --  101.00  77.00-180.00   52
102  \w     79.00 105.00   0.50    0.20    --  101.00  77.00 150.00   52
103  \w    120.00 147.00   0.50    0.20    --  101.00  59.00   0.00   54
104  \w     85.00 111.00   0.50    0.20    --  101.00  59.00   0.00   52
105  \w     80.00 154.00   0.50    0.20    --  101.00  68.00 -90.00  148
106  \w     85.00 136.00   0.50    0.20    --  101.00  59.00-150.00  102
107  \w     77.00 124.00   0.50    0.20    --  101.00  77.00 -60.00   94
108  \w    129.00 155.00   0.50    0.20    --  101.00  77.00  30.00   52
109  \w     85.00 111.00   0.50    0.20    --  101.00 -59.00 150.00   52
110  \w     40.00  66.00   0.50    0.20    --  101.00 -59.00 150.00   52
111  \w     77.00 102.00   0.50    0.20    --  101.00  77.00  60.00   50
112  \w     76.00 108.00   0.50    0.20    --  101.00  77.00  30.00   64
113  \w     80.00 145.00   0.50    0.20    --  101.00  68.00 150.00  130
114  \w     66.00 103.00   0.50    0.20    --  101.00 -17.00 -60.00   74
115  \w    121.00 147.00   0.50    0.20    --  101.00  59.00 -60.00   52
116  \w     86.00 117.00   0.50    0.20    --  101.00  59.00 -60.00   62
117  \w     32.00  63.00   0.50    0.20    --  101.00 -17.00 -60.00   62
118  \w    122.00 148.00   0.50    0.20    --  101.00  77.00 -30.00   52
119  \w     76.00 102.00   0.50    0.20    --  101.00  77.00 -90.00   52
120  \w     76.00 102.00   0.50    0.20    --  101.00  77.00 -30.00   52
121  \w     76.00 119.00   0.50    0.20    --  101.00  77.00  90.00   86
122  \w    132.00 157.00   0.50    0.20    --  101.00  68.00  60.00   50
123  \w     80.00 106.00   0.50    0.20    --  101.00  68.00  60.00   52
124  \w     76.00 102.00   0.50    0.20    --  101.00  77.00   0.00   52
125  \w     85.00 110.00   0.50    0.20    --  101.00 -33.00 -30.00   50
126  \w     41.00  67.00   0.50    0.20    --  101.00 -33.00 -30.00   52
127  \w     78.00 150.00   0.50    0.20    --  101.00  77.00-150.00  144
;
_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      0.0313728000
_diffrn_orient_matrix_UB_12      0.1579702000
_diffrn_orient_matrix_UB_13      -0.0096572000
_diffrn_orient_matrix_UB_21      -0.1736482000
_diffrn_orient_matrix_UB_22      0.0628360000
_diffrn_orient_matrix_UB_23      0.0209902000
_diffrn_orient_matrix_UB_31      0.0001241000
_diffrn_orient_matrix_UB_32      -0.0001013000
_diffrn_orient_matrix_UB_33      0.1387165000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16363
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.987
_diffrn_reflns_theta_min         4.035
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87696
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0247
_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^)+(0.0279P)^2^+0.4765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0615
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3179
_reflns_number_total             3388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00822e2.cif
_cod_data_source_block           7072-9949_emt105
_cod_database_code               1555072
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 F3'
_shelx_estimated_absorpt_t_max   0.495
_shelx_estimated_absorpt_t_min   0.280
_reflns_odcompleteness_completeness 99.88
_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
2.a Ternary CH refined with riding coordinates:
 C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C17(H17), C19(H19), C21(H21), C26(H26), C30(H30), C32(H32),
 C34(H34), C35(H35), C38(H38), C39(H39), C42(H42)
;
_shelx_res_checksum              8374
_shelx_hkl_checksum              9334
_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 1.408
_oxdiff_exptl_absorpt_empirical_full_min 0.858