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_1555075
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-10-23
_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                90
_cell_angle_beta                 103.732(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1714(3)
_cell_length_b                   36.8462(10)
_cell_length_c                   10.1929(3)
_cell_measurement_reflns_used    12584
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.8500
_cell_measurement_theta_min      2.4500
_cell_volume                     3710.88(19)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     -9.00  33.00   0.50    0.87    --   41.35-109.00 -20.00   84
  2  \w     39.00  66.00   0.50    0.87    --   41.35-109.00 -20.00   54
  3  \w     65.00 110.00   0.50    4.00    --  101.00-109.00 -20.00   90
  4  \w     82.00 150.00   0.50    4.00    --  101.00 109.00  75.00  136
  5  \w    -77.00 -50.00   0.50    0.87    --  -41.35 -32.00-150.00   54
  6  \w    -75.00 -46.00   0.50    0.87    --  -41.35 109.00  75.00   58
  7  \w    -49.00  21.00   0.50    0.87    --  -41.35  32.00  90.00  140
  8  \w    -65.00  10.00   0.50    0.87    --  -41.35  77.00-180.00  150
  9  \w   -106.00 -79.00   0.50    0.87    --  -41.35 -32.00-150.00   54
 10  \w    -43.00 -16.00   0.50    0.87    --  -41.35 109.00  75.00   54
 11  \w    -42.00  22.00   0.50    0.87    --  -41.35  65.00 120.00  128
 12  \w     -6.00  20.00   0.50    0.87    --   41.35 -54.00 -90.00   52
 13  \w     24.00 102.00   0.50    0.87    --   41.35  54.00 -90.00  156
 14  \w     25.00  57.00   0.50    0.87    --   41.35 -54.00 -90.00   64
 15  \w      8.00  41.00   0.50    0.87    --   41.35 -65.00 -30.00   66
 16  \w     76.00 105.00   0.50    0.87    --   41.35  65.00 120.00   58
 17  \w     72.00  99.00   0.50    0.87    --   41.35  65.00-180.00   54
 18  \w     23.00  58.00   0.50    0.87    --   41.35  65.00-180.00   70
 19  \w     52.00  97.00   0.50    4.00    --  101.00 -42.00   0.00   90
 20  \w    116.00 150.00   0.50    4.00    --  101.00  33.00 -30.00   68
 21  \w     39.00  98.00   0.50    4.00    --  101.00 -87.00 -30.00  118
 22  \w     37.00 105.00   0.50    4.00    --  101.00 -33.00 -90.00  136
 23  \w     77.00 131.00   0.50    4.00    --  101.00  77.00 120.00  108
 24  \w     39.00 118.00   0.50    4.00    --  101.00 -59.00 120.00  158
 25  \w     78.00 124.00   0.50    4.00    --  101.00-133.00 120.00   92
 26  \w     40.00  67.00   0.50    4.00    --  101.00-133.00 120.00   54
 27  \w     88.00 118.00   0.50    4.00    --  101.00  17.00-120.00   60
 28  \w    109.00 143.00   0.50    4.00    --  101.00   8.00 150.00   68
 29  \w     44.00 123.00   0.50    4.00    --  101.00 -68.00   0.00  158
 30  \w     45.00  90.00   0.50    4.00    --  101.00 -68.00 -30.00   90
 31  \w     72.00  99.00   0.50    4.00    --  101.00   8.00 150.00   54
 32  \w     90.00 136.00   0.50    4.00    --  101.00  17.00  30.00   92
 33  \w     38.00  65.00   0.50    4.00    --  101.00 -77.00  30.00   54
 34  \w     92.00 118.00   0.50    4.00    --  101.00 -77.00  30.00   52
 35  \w    117.00 156.00   0.50    4.00    --  101.00  77.00  30.00   78
 36  \w    125.00 154.00   0.50    4.00    --  101.00  33.00  30.00   58
 37  \w    120.00 157.00   0.50    4.00    --  101.00  33.00-120.00   74
 38  \w     82.00 107.00   0.50    4.00    --  101.00 109.00  75.00   50
 39  \w   -104.00 -53.00   0.50    0.87    --  -41.35 -21.00 -60.00  102
 40  \w   -104.00 -34.00   0.50    0.87    --  -41.35 -77.00  30.00  140
 41  \w    -55.00  15.00   0.50    0.87    --  -41.35  43.00 -60.00  140
 42  \w     15.00  41.00   0.50    0.87    --   41.35-138.00 -30.00   52
 43  \w      4.00  51.00   0.50    0.87    --   41.35 -21.00  60.00   94
 44  \w     57.00  84.00   0.50    0.87    --   41.35  32.00 -30.00   54
 45  \w     48.00  79.00   0.50    0.87    --   41.35-138.00 -30.00   62
 46  \w    -20.00  17.00   0.50    0.87    --   41.35 -65.00-150.00   74
 47  \w     40.00  68.00   0.50    4.00    --  101.00-133.00-180.00   56
 48  \w     89.00 121.00   0.50    4.00    --  101.00  17.00-150.00   64
 49  \w     82.00 110.00   0.50    4.00    --  101.00 -25.00 -30.00   56
 50  \w    130.00 157.00   0.50    4.00    --  101.00  17.00-150.00   54
 51  \w     99.00 124.00   0.50    4.00    --  101.00  -8.00  60.00   50
 52  \w     67.00  76.50   0.50    4.00    --  101.00 -59.00-150.00   19
;
_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      0.0077524000
_diffrn_orient_matrix_UB_12      0.0361935000
_diffrn_orient_matrix_UB_13      0.0773307000
_diffrn_orient_matrix_UB_21      -0.0824774000
_diffrn_orient_matrix_UB_22      0.0186548000
_diffrn_orient_matrix_UB_23      -0.1286104000
_diffrn_orient_matrix_UB_31      -0.1320851000
_diffrn_orient_matrix_UB_32      -0.0095600000
_diffrn_orient_matrix_UB_33      0.0410571000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28863
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.000
_diffrn_reflns_theta_min         2.398
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62385
_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    1.312
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.952
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0846P)^2^+2.6462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1543
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6148
_reflns_number_total             7038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00822e2.cif
_cod_data_source_block           7072-9911_emt086
_cod_original_cell_volume        3710.87(19)
_cod_database_code               1555075
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.864
_shelx_estimated_absorpt_t_min   0.809
_reflns_odcompleteness_completeness 99.89
_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:
 C4B(H4B), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3B(H3BA,H3BB), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C8B(H8B), C22B(H22B), C6(H6), C16(H16), C22(H22), C9B(H9B),
 C6B(H6B), C18(H18), C18B(H18B), C7B(H7B), C21(H21), C19B(H19B), C21B(H21B),
 C8(H8), C20(H20), C7(H7), C12B(H12B), C20B(H20B), C19(H19), C16B(H16B),
 C14(H14), C14B(H14B)
2.d Idealised Me refined as rotating group:
 C23(H23D,H23E,H23F), C24(H24D,H24E,H24F), C23B(H23A,H23B,H23C), C24B(H24A,
 H24B,H24C)
;
_shelx_res_checksum              52995
_shelx_hkl_checksum              69498
_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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.285