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_1555073
_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 H19 Cl2 F3 O2'
_chemical_formula_sum            'C24 H19 Cl2 F3 O2'
_chemical_formula_weight         467.29
_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                74.791(4)
_cell_angle_beta                 80.463(4)
_cell_angle_gamma                72.449(5)
_cell_formula_units_Z            2
_cell_length_a                   9.2224(5)
_cell_length_b                   10.2968(5)
_cell_length_c                   11.9735(5)
_cell_measurement_reflns_used    7152
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.5640
_cell_measurement_theta_min      3.7710
_cell_volume                     1041.48(9)
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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   -106.00 -36.00   0.50    0.50    --  -41.35 -31.00  22.00  140
  2  \w    -27.00   0.00   0.50    0.50    --  -41.35  31.00-177.00   54
  3  \w     -6.00  49.00   0.50    0.50    --   41.35 -31.00  22.00  110
  4  \w     37.00 103.00   0.50    0.50    --   41.35  31.00-177.00  132
  5  \w     94.00 148.00   0.50    2.00    --  101.00  31.00-177.00  108
  6  \w     35.00 109.00   0.50    2.00    --  101.00 -31.00  22.00  148
  7  \w    -56.00 -16.00   0.50    0.50    --  -41.35  54.00-180.00   80
  8  \w    -10.00  16.00   0.50    0.50    --  -41.35  54.00  60.00   52
  9  \w    -10.00  17.00   0.50    0.50    --  -41.35  54.00-180.00   54
 10  \w    -56.00 -16.00   0.50    0.50    --  -41.35  54.00  60.00   80
 11  \w    -39.00   6.00   0.50    0.50    --  -41.35  43.00   0.00   90
 12  \w    -11.00  15.00   0.50    0.50    --   41.35 -89.00 -30.00   52
 13  \w     49.00  92.00   0.50    0.50    --   41.35  43.00-120.00   86
 14  \w    -23.00  62.00   0.50    0.50    --   41.35 -77.00 -90.00  170
 15  \w     42.00  67.00   0.50    0.50    --   41.35  32.00 -30.00   50
 16  \w     17.00  54.00   0.50    0.50    --   41.35  77.00-120.00   74
 17  \w    -18.00  65.00   0.50    0.50    --   41.35 -77.00   0.00  166
 18  \w    -19.00   8.00   0.50    0.50    --   41.35 -65.00 120.00   54
 19  \w     22.00  48.00   0.50    0.50    --   41.35 -54.00 150.00   52
 20  \w     31.00  56.00   0.50    0.50    --   41.35 -89.00 -30.00   50
 21  \w    -12.00  13.00   0.50    0.50    --   41.35 -54.00 150.00   50
 22  \w     59.00 105.00   0.50    0.50    --   41.35  77.00-120.00   92
 23  \w     52.00  95.00   0.50    0.50    --   41.35-138.00-180.00   86
 24  \w     34.00  59.00   0.50    0.50    --   41.35 -65.00 120.00   50
 25  \w    112.00 156.00   0.50    2.00    --  101.00  42.00 150.00   88
 26  \w     47.00  90.00   0.50    2.00    --  101.00-111.00-150.00   86
 27  \w    123.00 155.00   0.50    2.00    --  101.00  25.00  60.00   64
 28  \w     40.00  85.00   0.50    2.00    --  101.00 -68.00  60.00   90
 29  \w     72.00  97.00   0.50    2.00    --  101.00-133.00  30.00   50
 30  \w     41.00  67.00   0.50    2.00    --  101.00-133.00  30.00   52
 31  \w     47.00 101.00   0.50    2.00    --  101.00 -25.00 120.00  108
 32  \w     88.00 114.00   0.50    2.00    --  101.00 -68.00  60.00   52
 33  \w     42.00 110.00   0.50    2.00    --  101.00 -25.00-150.00  136
 34  \w     85.00 149.00   0.50    2.00    --  101.00  59.00   0.00  128
 35  \w     81.00 116.00   0.50    2.00    --  101.00 -50.00 150.00   70
 36  \w     85.00 111.00   0.50    2.00    --  101.00  59.00  60.00   52
 37  \w     39.00 115.00   0.50    2.00    --  101.00-111.00  60.00  152
 38  \w     97.00 155.00   0.50    2.00    --  101.00  25.00 120.00  116
 39  \w    103.00 154.00   0.50    2.00    --  101.00  42.00  30.00  102
 40  \w     53.00 117.00   0.50    2.00    --  101.00 -50.00  60.00  128
 41  \w     82.00 116.00   0.50    2.00    --  101.00 -87.00  60.00   68
 42  \w     47.00  73.00   0.50    2.00    --  101.00 -59.00-120.00   52
 43  \w    128.00 153.00   0.50    2.00    --  101.00  68.00 -60.00   50
 44  \w     38.00 115.00   0.50    2.00    --  101.00 -50.00 -60.00  154
 45  \w     92.00 153.00   0.50    2.00    --  101.00  33.00 -90.00  122
 46  \w     65.00 105.00   0.50    2.00    --  101.00-111.00-120.00   80
 47  \w     38.00 123.00   0.50    2.00    --  101.00 -77.00-150.00  170
 48  \w     37.00  79.00   0.50    2.00    --  101.00 -87.00  60.00   84
 49  \w     77.00 114.00   0.50    2.00    --  101.00-111.00-180.00   74
 50  \w     44.00  79.00   0.50    2.00    --  101.00-133.00   0.00   70
 51  \w     91.00 116.00   0.50    2.00    --  101.00-133.00   0.00   50
 52  \w     45.00  71.00   0.50    2.00    --  101.00 -50.00 150.00   52
 53  \w     40.00 122.00   0.50    2.00    --  101.00-133.00  60.00  164
 54  \w     47.00  73.00   0.50    2.00    --  101.00-133.00-160.00   52
 55  \w    -32.00  -7.00   0.50    0.50    --    8.00 112.00  53.28   50
 56  \w    -22.00   3.00   0.50    0.50    --   16.00 108.00-115.27   50
 57  \w    -43.00 -18.00   0.50    0.50    --   24.00 153.00  26.46   50
 58  \w     -3.00  22.00   0.50    0.50    --   28.00  94.00-101.99   50
 59  \w      3.00  28.00   0.50    0.50    --   32.00  90.00-117.85   50
 60  \w      2.00  27.00   0.50    0.50    --   32.00  91.00  35.56   50
 61  \w      3.00  28.00   0.50    0.50    --   32.00  90.00 174.27   50
 62  \w      3.00  28.00   0.50    0.50    --   32.00  90.00 112.01   50
 63  \w      4.00  29.00   0.50    0.50    --   32.00  88.00 -27.59   50
 64  \w     10.00  35.00   0.50    0.50    --   36.00  83.00  81.59   50
 65  \w     10.00  35.00   0.50    0.50    --   36.00  83.00 132.27   50
 66  \w      9.00  34.00   0.50    0.50    --   36.00  85.00 -65.61   50
 67  \w     14.00  39.00   0.50    0.50    --   40.00  82.00  -6.09   50
 68  \w     46.00  72.00   0.50    0.50    --   41.35-104.00-150.00   52
 69  \w     19.00  44.00   0.50    0.50    --   44.00  81.00 138.27   50
 70  \w     19.00  44.00   0.50    0.50    --   44.00  79.00 102.47   50
 71  \w     19.00  44.00   0.50    0.50    --   44.00  80.00-171.04   50
 72  \w     18.00  43.00   0.50    0.50    --   44.00  82.00  25.66   50
 73  \w     19.00  44.00   0.50    0.50    --   44.00  80.00  55.87   50
 74  \w     19.00  44.00   0.50    0.50    --   44.00  81.00 -47.50   50
 75  \w     19.00  44.00   0.50    0.50    --   44.00  80.00-118.98   50
 76  \w     28.00  54.00   0.50    0.50    --   48.00  77.00 -97.97   52
 77  \w     27.00  53.00   0.50    0.50    --   52.00  76.00 -12.47   52
 78  \w     27.00  53.00   0.50    0.50    --   52.00  77.00 120.53   52
 79  \w     27.00  53.00   0.50    0.50    --   52.00  77.00 152.04   52
 80  \w     29.00  55.00   0.50    0.50    --   52.00  76.00-136.53   52
 81  \w     29.00  69.00   0.50    0.50    --   52.00  74.00  23.76   80
 82  \w     28.00  54.00   0.50    0.50    --   52.00  77.00-176.62   52
 83  \w     31.00  57.00   0.50    0.50    --   56.00  77.00  68.94   52
 84  \w     42.00  68.00   0.50    0.50    --   60.00  67.00-118.35   52
 85  \w     40.00  86.00   0.50    0.50    --   60.00  64.00  79.84   92
 86  \w    103.00 128.00   0.50    0.50    --   64.00  72.00 -52.70   50
 87  \w     42.00  92.00   0.50    0.50    --   64.00  72.00 -52.70  100
 88  \w     41.00  72.00   0.50    0.50    --   64.00  77.00 120.97   62
 89  \w     41.00  77.00   0.50    0.50    --   64.00  72.00 175.63   72
 90  \w     80.00 106.00   0.50    0.50    --   64.00  72.00 175.63   52
 91  \w     43.00  69.00   0.50    0.50    --   64.00  72.00-148.40   52
 92  \w     39.00  64.00   0.50    0.50    --   64.00  77.00 -93.83   50
 93  \w     43.00 116.00   0.50    0.50    --   68.00  77.00 -19.83  146
 94  \w    104.00 130.00   0.50    0.50    --   68.00  66.00  32.08   52
 95  \w     56.00  82.00   0.50    0.50    --   68.00  66.00  32.08   52
 96  \w     46.00  72.00   0.50    0.50    --   68.00  74.00  98.04   52
 97  \w     47.00  91.50   0.50    2.00    --   72.00  76.00   5.48   89
;
_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      0.0298432000
_diffrn_orient_matrix_UB_12      -0.1515860000
_diffrn_orient_matrix_UB_13      -0.0115775000
_diffrn_orient_matrix_UB_21      -0.1646617000
_diffrn_orient_matrix_UB_22      0.0012165000
_diffrn_orient_matrix_UB_23      0.0520099000
_diffrn_orient_matrix_UB_31      -0.0544758000
_diffrn_orient_matrix_UB_32      0.0544396000
_diffrn_orient_matrix_UB_33      -0.1228685000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.983
_diffrn_reflns_theta_min         3.843
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71885
_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    1.490
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0994P)^2^+0.6549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3470
_reflns_number_total             3943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00822e2.cif
_cod_data_source_block           7072-9926_emt073
_cod_original_cell_volume        1041.48(10)
_cod_database_code               1555073
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.719
_shelx_estimated_absorpt_t_min   0.417
_reflns_odcompleteness_completeness 99.16
_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:
 C16(H16), C12(H12), C18(H18), C9(H9), C6(H6), C13(H13), C22(H22), C14(H14),
 C21(H21), C15(H15)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              15892
_shelx_hkl_checksum              98320
_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 2.623
_oxdiff_exptl_absorpt_empirical_full_min 0.662