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_1555063
_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 O2'
_chemical_formula_sum            'C24 H21 F3 O2'
_chemical_formula_weight         398.41
_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                94.5890(10)
_cell_angle_beta                 106.2794(11)
_cell_angle_gamma                98.2135(11)
_cell_formula_units_Z            4
_cell_length_a                   9.28774(13)
_cell_length_b                   13.98378(18)
_cell_length_c                   16.25245(18)
_cell_measurement_reflns_used    33355
_cell_measurement_temperature    100(5)
_cell_measurement_theta_max      71.9530
_cell_measurement_theta_min      2.7880
_cell_volume                     1989.34(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(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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    -20.00  17.00   0.50    0.20    --   41.35 -84.00-120.00   74
  2  \w     25.00  68.00   0.50    0.20    --   41.35 -84.00-120.00   86
  3  \w     37.00 106.00   0.50    0.80    --  101.00 -84.00-120.00  138
  4  \w     78.00 109.00   0.50    0.80    --  101.00  84.00   0.00   62
  5  \w     -2.00  26.00   0.50    0.20    --  -41.35  21.00   0.00   56
  6  \w    -68.00 -42.00   0.50    0.20    --  -41.35  84.00   0.00   52
  7  \w    -49.00 -14.00   0.50    0.20    --  -41.35  21.00   0.00   70
  8  \w    -58.00  -4.00   0.50    0.20    --  -41.35  54.00  60.00  108
  9  \w    -39.00   0.00   0.50    0.20    --  -41.35  32.00-120.00   78
 10  \w    -68.00 -25.00   0.50    0.20    --  -41.35 -54.00  30.00   86
 11  \w    -90.00 -52.00   0.50    0.20    --  -41.35 138.00 -30.00   76
 12  \w    -53.00  19.00   0.50    0.20    --  -41.35  43.00-180.00  144
 13  \w    -91.00 -12.00   0.50    0.20    --  -41.35 138.00-180.00  158
 14  \w    -11.00  18.00   0.50    0.20    --  -41.35  84.00   0.00   58
 15  \w   -104.00 -36.00   0.50    0.20    --  -41.35 -43.00 -60.00  136
 16  \w   -100.00 -72.00   0.50    0.20    --  -41.35 -43.00  30.00   56
 17  \w    -54.00 -10.00   0.50    0.20    --  -41.35  54.00-150.00   88
 18  \w    -65.00 -40.00   0.50    0.20    --  -41.35 -43.00  30.00   50
 19  \w    -43.00  -4.00   0.50    0.20    --  -41.35  54.00 -60.00   78
 20  \w    -26.00   8.00   0.50    0.20    --   41.35 -11.00  90.00   68
 21  \w     13.00  64.00   0.50    0.20    --   41.35 -11.00  90.00  102
 22  \w     30.00 104.00   0.50    0.20    --   41.35  54.00  90.00  148
 23  \w     24.00  69.00   0.50    0.20    --   41.35-104.00 150.00   90
 24  \w    -14.00  18.00   0.50    0.20    --   41.35-104.00 150.00   64
 25  \w     50.00  77.00   0.50    0.20    --   41.35-138.00  90.00   54
 26  \w     50.00 105.00   0.50    0.20    --   41.35  32.00-120.00  110
 27  \w     43.00 100.00   0.50    0.80    --  101.00 -77.00  90.00  114
 28  \w     40.00 106.00   0.50    0.80    --  101.00 -25.00-180.00  132
 29  \w     88.00 157.00   0.50    0.80    --  101.00  42.00  60.00  138
 30  \w     97.00 129.00   0.50    0.80    --  101.00 -87.00 -60.00   64
 31  \w     47.00  81.00   0.50    0.80    --  101.00 -87.00 -60.00   68
 32  \w     42.00  68.00   0.50    0.80    --  101.00 -33.00 -30.00   52
 33  \w     64.00 108.00   0.50    0.80    --  101.00-111.00-180.00   88
 34  \w     50.00 113.00   0.50    0.80    --  101.00-111.00  90.00  126
 35  \w     92.00 124.00   0.50    0.80    --  101.00  25.00 120.00   64
 36  \w     48.00 110.00   0.50    0.80    --  101.00-111.00-120.00  124
 37  \w     35.00  91.00   0.50    0.80    --  101.00-111.00-150.00  112
 38  \w     48.00  82.00   0.50    0.80    --  101.00 -25.00 -90.00   68
 39  \w     61.00 114.00   0.50    0.80    --  101.00-111.00 -60.00  106
 40  \w     91.00 157.00   0.50    0.80    --  101.00 111.00 -90.00  132
 41  \w     82.00 156.00   0.50    0.80    --  101.00  93.00 -60.00  148
 42  \w     72.00 113.00   0.50    0.80    --  101.00-111.00   0.00   82
 43  \w     88.00 157.00   0.50    0.80    --  101.00  93.00 -30.00  138
 44  \w     51.00  98.00   0.50    0.80    --  101.00 -68.00  30.00   94
 45  \w     40.00 101.00   0.50    0.80    --  101.00-133.00-180.00  122
 46  \w     80.00 112.00   0.50    0.80    --  101.00  68.00  90.00   64
 47  \w    127.00 156.00   0.50    0.80    --  101.00  68.00  90.00   58
 48  \w     79.00 157.00   0.50    0.80    --  101.00   8.00  60.00  156
 49  \w     39.00 120.00   0.50    0.80    --  101.00 -59.00 -60.00  162
 50  \w     69.00  95.00   0.50    0.80    --  101.00 -33.00 120.00   52
 51  \w     76.00 125.00   0.50    0.80    --  101.00  77.00 150.00   98
 52  \w     82.00 108.00   0.50    0.80    --  101.00  93.00-150.00   52
 53  \w     74.00 103.00   0.50    0.80    --  101.00 -33.00 -30.00   58
 54  \w     44.00 107.00   0.50    0.80    --  101.00 -42.00-150.00  126
 55  \w    105.00 147.00   0.50    0.80    --  101.00 111.00-120.00   84
 56  \w    122.00 157.00   0.50    0.80    --  101.00  84.00   0.00   70
 57  \w    -65.00 -39.00   0.50    0.20    --  -41.35  84.00   0.00   52
 58  \w    -39.00 -14.00   0.50    0.20    --   12.00 129.00 144.37   50
 59  \w    -28.00  -3.00   0.50    0.20    --   16.00 119.00 -24.82   50
 60  \w    -13.00  12.00   0.50    0.20    --   24.00 106.00  18.84   50
 61  \w     -3.00  22.00   0.50    0.20    --   28.00  95.00 105.95   50
 62  \w     -2.00  23.00   0.50    0.20    --   28.00  93.00 171.65   50
 63  \w     -4.00  21.00   0.50    0.20    --   28.00  97.00 -25.01   50
 64  \w     -3.00  22.00   0.50    0.20    --   28.00  95.00-114.31   50
 65  \w      4.00  29.00   0.50    0.20    --   32.00  88.00  48.53   50
 66  \w      4.00  29.00   0.50    0.20    --   32.00  88.00-135.79   50
 67  \w      9.00  34.00   0.50    0.20    --   36.00  85.00-128.61   50
 68  \w      9.00  34.00   0.50    0.20    --   36.00  85.00 -42.35   50
 69  \w      9.00  34.00   0.50    0.20    --   36.00  85.00   3.08   50
 70  \w      9.00  34.00   0.50    0.20    --   36.00  84.00  91.85   50
 71  \w      9.00  46.00   0.50    0.20    --   41.35 -32.00   0.00   74
 72  \w     18.00  43.00   0.50    0.20    --   44.00  82.00 -14.44   50
 73  \w     19.00  44.00   0.50    0.20    --   44.00  81.00 -50.11   50
 74  \w     19.00  44.00   0.50    0.20    --   44.00  81.00  39.48   50
 75  \w     18.00  43.00   0.50    0.20    --   44.00  82.00 126.77   50
 76  \w     19.00  44.00   0.50    0.20    --   44.00  80.00  86.19   50
 77  \w     19.00  44.00   0.50    0.20    --   44.00  80.00 -84.89   50
 78  \w     18.00  43.00   0.50    0.20    --   44.00  82.00 164.81   50
 79  \w     25.00  51.00   0.50    0.20    --   48.00  77.00-153.24   52
 80  \w     27.00  52.00   0.50    0.20    --   52.00  77.00 -28.60   50
 81  \w     29.00  55.00   0.50    0.20    --   52.00  75.00 107.60   52
 82  \w     87.00 116.00   0.50    0.20    --   52.00  76.00-125.48   58
 83  \w     28.00  54.00   0.50    0.20    --   52.00  77.00 -68.51   52
 84  \w     27.00  53.00   0.50    0.20    --   52.00  76.00  16.84   52
 85  \w     27.00  53.00   0.50    0.20    --   52.00  76.00-125.48   52
 86  \w     31.00  57.00   0.50    0.20    --   56.00  77.00 134.56   52
 87  \w     32.00  58.00   0.50    0.20    --   56.00  77.00 171.00   52
 88  \w     32.00  58.00   0.50    0.20    --   56.00  77.00  38.39   52
 89  \w     95.00 120.00   0.50    0.20    --   56.00  74.00-119.58   50
 90  \w     35.00  61.00   0.50    0.20    --   56.00  74.00-119.58   52
 91  \w     41.00  80.00   0.50    0.20    --   60.00  73.00-109.17   78
 92  \w     41.00  70.00   0.50    0.20    --   64.00  72.00-169.67   58
 93  \w     44.00  70.00   0.50    0.20    --   64.00  66.00 100.50   52
 94  \w     42.00  68.00   0.50    0.20    --   64.00  69.00   1.65   52
 95  \w     45.00  84.00   0.50    0.20    --   68.00  73.00 -34.35   78
 96  \w     43.00 107.00   0.50    0.20    --   68.00  77.00 140.90  128
 97  \w     83.00 119.00   0.50    0.20    --   68.00  62.00-155.76   72
 98  \w     50.00  76.00   0.50    0.20    --   68.00  62.00-155.76   52
 99  \w     47.00  96.00   0.50    0.20    --   68.00  69.00  55.53   98
100  \w     97.00 130.00   0.50    0.20    --   68.00  76.00  96.78   66
101  \w     46.00  74.00   0.50    0.20    --   68.00  76.00  96.78   56
102  \w     53.00  87.00   0.50    0.80    --   76.00  72.00 -70.28   68
103  \w     57.00  86.00   0.50    0.80    --   80.00  74.00   3.10   58
104  \w     61.00  87.00   0.50    0.80    --   84.00  73.00  69.55   52
105  \w    104.00 130.00   0.50    0.80    --   88.00  75.00 119.79   52
106  \w     64.00  89.00   0.50    0.80    --   88.00  75.00 119.79   50
107  \w     38.00  63.00   0.50    0.80    --  101.00 -33.00   0.00   50
108  \w    129.00 155.00   0.50    0.80    --  101.00  77.00  60.00   52
109  \w     76.00 112.00   0.50    0.80    --  101.00  77.00  60.00   72
110  \w     76.00 150.00   0.50    0.80    --  101.00  77.00-120.00  148
111  \w     83.00 109.00   0.50    0.80    --  101.00  59.00 -30.00   52
112  \w     76.00 102.00   0.50    0.80    --  101.00  77.00-150.00   52
113  \w     76.00 113.00   0.50    0.80    --  101.00  77.00 -30.00   74
114  \w    127.00 153.00   0.50    0.80    --  101.00  59.00 -30.00   52
115  \w     81.00 117.00   0.50    0.80    --  101.00  68.00   0.00   72
116  \w    130.00 156.00   0.50    0.80    --  101.00  59.00  90.00   52
117  \w     71.00 100.00   0.50    0.80    --  101.00 -33.00 -90.00   58
118  \w     76.00 124.00   0.50    0.80    --  101.00  77.00  90.00   96
119  \w    127.00 154.00   0.50    0.80    --  101.00  77.00  90.00   54
120  \w     83.00 109.00   0.50    0.80    --  101.00  59.00  90.00   52
121  \w     95.00 120.00   0.50    0.80    --  101.00 -59.00 120.00   50
122  \w     42.00  68.00   0.50    0.80    --  101.00 -33.00 -90.00   52
123  \w     39.00  65.00   0.50    0.80    --  101.00 -59.00 120.00   52
124  \w    129.00 155.00   0.50    0.80    --  101.00  77.00 -60.00   52
125  \w     76.00 101.00   0.50    0.80    --  101.00  77.00 -60.00   50
126  \w     83.00 145.00   0.50    0.80    --  101.00  59.00-180.00  124
127  \w    129.00 154.00   0.50    0.80    --  101.00  77.00-180.00   50
128  \w     80.00 139.00   0.50    0.80    --  101.00  68.00 120.00  118
129  \w     83.00 157.00   0.50    0.80    --  101.00  59.00-150.00  148
130  \w    111.00 149.00   0.50    0.80    --  101.00  73.00-131.98   76
131  \w     76.00 101.00   0.50    0.80    --  101.00  77.00-180.00   50
132  \w    125.00 151.00   0.50    0.80    --  101.00  77.00 120.00   52
133  \w     77.00 114.00   0.50    0.80    --  101.00  77.00 120.00   74
134  \w     77.00 134.00   0.50    0.80    --  101.00  77.00  30.00  114
135  \w     78.00 104.00   0.50    0.80    --  101.00  73.00-131.98   52
136  \w    126.00 157.00   0.50    0.80    --  101.00  68.00 150.00   62
137  \w     80.00 121.00   0.50    0.80    --  101.00  68.00 150.00   82
138  \w     76.00 137.00   0.50    0.80    --  101.00  77.00 -90.00  122
139  \w     73.00  99.00   0.50    0.80    --  101.00 -33.00   0.00   52
140  \w     84.00 121.00   0.50    0.80    --  101.00  59.00 -90.00   74
;
_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      0.1250423000
_diffrn_orient_matrix_UB_12      -0.0123648000
_diffrn_orient_matrix_UB_13      -0.0434008000
_diffrn_orient_matrix_UB_21      0.1183338000
_diffrn_orient_matrix_UB_22      0.0671931000
_diffrn_orient_matrix_UB_23      0.0759537000
_diffrn_orient_matrix_UB_31      0.0337540000
_diffrn_orient_matrix_UB_32      -0.0890115000
_diffrn_orient_matrix_UB_33      0.0475075000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41358
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.116
_diffrn_reflns_theta_min         2.855
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92260
_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    1.330
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         7766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0438P)^2^+1.0736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7548
_reflns_number_total             7766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00822e2.cif
_cod_data_source_block           7072-9949_emt079_prism
_cod_database_code               1555063
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.789
_shelx_estimated_absorpt_t_min   0.664
_reflns_odcompleteness_completeness 99.86
_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:
 C1(H1), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C40(H40), C5(H5), C44(H44), C11(H11), C51(H51), C52(H52), C35(H35),
 C23(H23), C37(H37), C41(H41), C15(H15), C34(H34), C6(H6), C43(H43), C14(H14),
 C12(H12), C50(H50), C19(H19), C22(H22), C48(H48), C21(H21), C49(H49), C20(H20)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C29(H29A,H29B,H29C), C46(H46A,H46B,H46C), C58(H58A,H58B,
 H58C)
;
_shelx_res_checksum              53860
_shelx_hkl_checksum              37199
_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 1.188
_oxdiff_exptl_absorpt_empirical_full_min 0.774