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_1555067
_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         'C23 H19 F3 O'
_chemical_formula_sum            'C23 H19 F3 O'
_chemical_formula_weight         368.38
_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                91.174(2)
_cell_angle_beta                 116.274(2)
_cell_angle_gamma                107.926(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9918(2)
_cell_length_b                   10.2089(2)
_cell_length_c                   10.5751(2)
_cell_measurement_reflns_used    11409
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.7490
_cell_measurement_theta_min      4.5710
_cell_volume                     904.65(4)
_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    -83.00 -57.00   0.50    0.50    --  -41.49 127.00-173.00   52
  2  \w    -45.00  -8.00   0.50    0.50    --  -41.49 127.00-173.00   74
  3  \w    -93.00 -41.00   0.50    0.50    --  -41.49 143.00  -3.00  104
  4  \w     30.00  70.00   0.50    0.50    --   41.49-143.00 -58.00   80
  5  \w     46.00  91.00   0.50    0.50    --   41.49-127.00 110.00   90
  6  \w     70.00 103.00   0.50    1.50    --  101.00-127.00 110.00   66
  7  \w     83.00 116.00   0.50    1.50    --  101.00-143.00 -58.00   66
  8  \w    104.00 130.00   0.50    1.50    --  101.00 127.00-173.00   52
  9  \w    -35.00  24.00   0.50    0.50    --  -41.49  32.00   0.00  118
 10  \w    -67.00   1.00   0.50    0.50    --  -41.49  77.00   0.00  136
 11  \w    -51.00   2.00   0.50    0.50    --  -41.49  43.00  90.00  106
 12  \w    -92.00 -57.00   0.50    0.50    --  -41.49 -43.00   0.00   70
 13  \w     17.00  69.00   0.50    0.50    --   41.49 -89.00  90.00  104
 14  \w     34.00  93.00   0.50    0.50    --   41.49  32.00-180.00  118
 15  \w    -12.00  14.00   0.50    0.50    --   41.49 -43.00 150.00   52
 16  \w     74.00 103.00   0.50    0.50    --   41.49  43.00-120.00   58
 17  \w     40.00 105.00   0.50    0.50    --   41.49  32.00 -60.00  130
 18  \w     28.00  60.00   0.50    0.50    --   41.49  43.00-120.00   64
 19  \w     -8.00  45.00   0.50    0.50    --   41.49 -32.00 150.00  106
 20  \w    -14.00  12.00   0.50    0.50    --   41.49 -89.00  90.00   52
 21  \w     25.00  50.00   0.50    0.50    --   41.49 -43.00 150.00   50
 22  \w     76.00 101.00   0.50    0.50    --   41.49  32.00 150.00   50
 23  \w    -22.00  44.00   0.50    0.50    --   41.49 -32.00  30.00  132
 24  \w     93.00 134.00   0.50    1.50    --  101.00  33.00-120.00   82
 25  \w     82.00 155.00   0.50    1.50    --  101.00  68.00 120.00  146
 26  \w    116.00 157.00   0.50    1.50    --  101.00  93.00-120.00   82
 27  \w    101.00 153.00   0.50    1.50    --  101.00  33.00 -60.00  104
 28  \w     37.00 127.00   0.50    1.50    --  101.00 -87.00  90.00  180
 29  \w     82.00 107.00   0.50    1.50    --  101.00  93.00-120.00   50
 30  \w     94.00 157.00   0.50    1.50    --  101.00  77.00  90.00  126
 31  \w     38.00 125.00   0.50    1.50    --  101.00 -77.00 -60.00  174
 32  \w     40.00 112.00   0.50    1.50    --  101.00 -42.00  90.00  144
 33  \w     41.00 117.00   0.50    1.50    --  101.00 -50.00-180.00  152
 34  \w     53.00  78.00   0.50    1.50    --  101.00-111.00-120.00   50
 35  \w     93.00 119.00   0.50    1.50    --  101.00  33.00 120.00   52
 36  \w     64.00  89.00   0.50    1.50    --  101.00 -77.00 -90.00   50
 37  \w     92.00 152.00   0.50    1.50    --  101.00  25.00  60.00  120
 38  \w    103.00 129.00   0.50    1.50    --  101.00  59.00 -30.00   52
 39  \w    123.00 154.00   0.50    1.50    --  101.00  33.00-180.00   62
 40  \w     41.00 112.00   0.50    1.50    --  101.00 -42.00 -30.00  142
 41  \w     48.00 101.00   0.50    1.50    --  101.00 -42.00 -90.00  106
 42  \w     97.00 148.00   0.50    1.50    --  101.00  59.00-120.00  102
 43  \w     75.00 122.00   0.50    1.50    --  101.00-133.00  60.00   94
 44  \w     69.00 113.00   0.50    1.50    --  101.00-111.00 150.00   88
 45  \w     53.00 104.00   0.50    1.50    --  101.00-111.00 -60.00  102
 46  \w     95.00 124.00   0.50    1.50    --  101.00-133.00 -90.00   58
 47  \w     92.00 141.00   0.50    1.50    --  101.00  68.00-180.00   98
 48  \w     42.00 111.00   0.50    1.50    --  101.00 -59.00  90.00  138
 49  \w    100.00 156.00   0.50    1.50    --  101.00  59.00 150.00  112
 50  \w     86.00 111.00   0.50    1.50    --  101.00 143.00  -3.00   50
 51  \w     19.00  45.00   0.50    0.50    --   41.49  77.00-180.00   52
 52  \w    -42.00 -17.00   0.50    0.50    --    4.00 121.00  99.36   50
 53  \w    -27.00   4.00   0.50    0.50    --   16.00 116.00-105.70   62
 54  \w    -12.00  13.00   0.50    0.50    --   24.00 104.00  60.23   50
 55  \w    -40.00 -15.00   0.50    0.50    --   24.00 150.00-170.85   50
 56  \w     -3.00  22.00   0.50    0.50    --   28.00  95.00-120.68   50
 57  \w      3.00  28.00   0.50    0.50    --   32.00  89.00 -43.43   50
 58  \w      2.00  27.00   0.50    0.50    --   32.00  91.00 148.77   50
 59  \w      9.00  34.00   0.50    0.50    --   36.00  85.00 -94.02   50
 60  \w     10.00  35.00   0.50    0.50    --   36.00  82.00  32.15   50
 61  \w     15.00  40.00   0.50    0.50    --   40.00  79.00 -33.47   50
 62  \w     14.00  39.00   0.50    0.50    --   40.00  82.00  94.48   50
 63  \w     15.00  40.00   0.50    0.50    --   40.00  79.00-153.03   50
 64  \w     16.00  41.00   0.50    0.50    --   41.49  78.00 149.15   50
 65  \w     17.00  43.00   0.50    0.50    --   41.49  77.00 -90.00   52
 66  \w     18.00  43.00   0.50    0.50    --   44.00  82.00  -1.59   50
 67  \w     19.00  45.00   0.50    0.50    --   44.00  80.00  66.12   52
 68  \w     25.00  51.00   0.50    0.50    --   48.00  75.00 119.74   52
 69  \w     29.00  55.00   0.50    0.50    --   52.00  76.00  -7.14   52
 70  \w     28.00  54.00   0.50    0.50    --   52.00  75.00 -61.65   52
 71  \w     33.00  59.00   0.50    0.50    --   52.00  75.00  31.36   52
 72  \w     34.00  60.00   0.50    0.50    --   56.00  71.00-161.18   52
 73  \w     38.00  64.00   0.50    0.50    --   56.00  75.00 155.92   52
 74  \w     32.00  58.00   0.50    0.50    --   56.00  77.00 -58.68   52
 75  \w     40.00  65.00   0.50    0.50    --   60.00  65.00  82.66   50
 76  \w     41.00  67.00   0.50    0.50    --   60.00  65.00-106.54   52
 77  \w     35.00  66.00   0.50    0.50    --   60.00  77.00 135.39   62
 78  \w     71.00 113.00   0.50    0.50    --   60.00  65.00  82.66   84
 79  \w     42.00 102.00   0.50    0.50    --   64.00  73.00 -27.74  120
 80  \w     98.00 124.00   0.50    0.50    --   64.00  64.00 129.41   52
 81  \w     49.00  78.00   0.50    0.50    --   64.00  64.00 129.41   58
 82  \w     98.00 124.00   0.50    0.50    --   68.00  67.00  25.10   52
 83  \w     47.00  88.00   0.50    0.50    --   68.00  67.00  25.10   82
 84  \w     45.00  96.00   0.50    0.50    --   68.00  75.00 -43.07  102
 85  \w     43.00  79.00   0.50    0.50    --   68.00  77.00-150.16   72
 86  \w     54.00  79.00   0.50    1.50    --   76.00  70.00-108.05   50
 87  \w     53.00  97.00   0.50    1.50    --   76.00  73.00 172.06   88
 88  \w     53.00  79.00   0.50    1.50    --   76.00  72.00  88.99   52
 89  \w     60.00  86.00   0.50    1.50    --   76.00  53.00 173.82   52
 90  \w     93.00 134.00   0.50    1.50    --   84.00  73.00 -74.09   82
 91  \w     61.00  88.00   0.50    1.50    --   84.00  73.00 -74.09   54
 92  \w     64.00  90.00   0.50    1.50    --   88.00  76.00  87.95   52
 93  \w    123.00 149.00   0.50    1.50    --  101.00  77.00-150.00   52
 94  \w     76.00 102.00   0.50    1.50    --  101.00  77.00-150.00   52
 95  \w    120.00 156.00   0.50    1.50    --  101.00  77.00 -60.00   72
 96  \w     94.00 120.00   0.50    1.50    --  101.00  -8.00-180.00   52
 97  \w     76.00 116.00   0.50    1.50    --  101.00  77.00 -60.00   80
 98  \w     28.00  93.00   0.50    1.50    --  101.00  -8.00-180.00  130
 99  \w     73.00 109.00   0.50    1.50    --  101.00 -25.00 -30.00   72
100  \w     36.00  64.00   0.50    1.50    --  101.00 -25.00 -30.00   56
101  \w    117.00 153.00   0.50    1.50    --  101.00  77.00 -30.00   72
102  \w     76.00 103.00   0.50    1.50    --  101.00  77.00 -90.00   54
103  \w     77.00 103.00   0.50    1.50    --  101.00  77.00 -30.00   52
104  \w    122.00 148.00   0.50    1.50    --  101.00  77.00-180.00   52
105  \w    132.00 157.00   0.50    1.50    --  101.00  77.00   0.00   50
106  \w     76.00 117.00   0.50    1.50    --  101.00  77.00   0.00   82
107  \w     78.00 104.00   0.50    1.50    --  101.00  77.00-180.00   52
108  \w     76.00 129.00   0.50    1.50    --  101.00  77.00  60.00  106
109  \w     83.00 135.00   0.50    1.50    --  101.00  59.00-150.00  104
110  \w     76.00 101.00   0.50    1.50    --  101.00  77.00  90.00   50
111  \w     76.00 121.00   0.50    1.50    --  101.00  77.00  30.00   90
112  \w    132.00 157.00   0.50    1.50    --  101.00  77.00 120.00   50
113  \w     77.00 103.00   0.50    1.50    --  101.00 -33.00 120.00   52
114  \w     76.00 108.00   0.50    1.50    --  101.00  77.00 120.00   64
115  \w     41.00 105.00   0.50    1.50    --  101.00 -25.00-180.00  128
116  \w     77.00 103.00   0.50    1.50    --  101.00 -17.00  60.00   52
117  \w     76.00 102.00   0.50    1.50    --  101.00  77.00-120.00   52
118  \w     31.00  67.00   0.50    1.50    --  101.00 -17.00  60.00   72
119  \w    127.00 153.00   0.50    1.50    --  101.00  59.00   0.00   52
120  \w     85.00 111.00   0.50    1.50    --  101.00  59.00   0.00   52
121  \w     77.00 106.00   0.50    1.50    --  101.00  77.00 150.00   58
;
_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      0.0332437000
_diffrn_orient_matrix_UB_12      -0.1370636000
_diffrn_orient_matrix_UB_13      0.0283627000
_diffrn_orient_matrix_UB_21      0.1715588000
_diffrn_orient_matrix_UB_22      0.0846473000
_diffrn_orient_matrix_UB_23      0.1160279000
_diffrn_orient_matrix_UB_31      -0.0569938000
_diffrn_orient_matrix_UB_32      -0.0090621000
_diffrn_orient_matrix_UB_33      0.1142319000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16434
_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         71.964
_diffrn_reflns_theta_min         4.631
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81725
_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    1.352
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.042
_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     245
_refine_ls_number_reflns         3535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0493P)^2^+0.2809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3338
_reflns_number_total             3535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00822e2.cif
_cod_data_source_block           7072-9926_b-15a
_cod_original_cell_volume        904.65(3)
_cod_database_code               1555067
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C48 H40 F6 O1 '
_shelx_estimated_absorpt_t_max   0.834
_shelx_estimated_absorpt_t_min   0.704
_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:
 C5(H5), C7(H7), C17(H17), C19(H19), C20(H20), C11(H11), C18(H18), C14(H14),
 C21(H21), C8(H8), C13(H13), C12(H12), C15(H15)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              47053
_shelx_hkl_checksum              95830
_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 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.770