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_1555062
_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'
_chemical_formula_sum            'C23 H19 F3'
_chemical_formula_weight         352.38
_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     direct
_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                 115.595(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7304(4)
_cell_length_b                   18.6098(5)
_cell_length_c                   9.9301(4)
_cell_measurement_reflns_used    7923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6880
_cell_measurement_theta_min      4.6050
_cell_volume                     1788.36(12)
_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    'ShelXS (Sheldrick, 2008)'
_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 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   -102.00 -63.00   0.50    0.20    --  -41.35 -48.00 -32.00   78
  2  \w    -47.00  -9.00   0.50    0.20    --  -41.35  48.00 115.00   76
  3  \w    -56.00 -26.00   0.50    0.20    --  -41.35 -48.00 -32.00   60
  4  \w     51.00  78.00   0.50    0.20    --   41.35  48.00 115.00   54
  5  \w     38.00 105.00   0.50    0.66    --  101.00 -48.00 -32.00  134
  6  \w     91.00 154.00   0.50    0.66    --  101.00  48.00 115.00  126
  7  \w    -53.00  19.00   0.50    0.20    --  -41.35  43.00 -60.00  144
  8  \w    -61.00 -34.00   0.50    0.20    --  -41.35  11.00-120.00   54
  9  \w   -101.00 -25.00   0.50    0.20    --  -41.35 -65.00  90.00  152
 10  \w    -24.00   3.00   0.50    0.20    --  -41.35  11.00-120.00   54
 11  \w     56.00 106.00   0.50    0.20    --   41.35  32.00 -90.00  100
 12  \w     35.00  66.00   0.50    0.20    --   41.35  32.00   0.00   62
 13  \w     71.00  99.00   0.50    0.20    --   41.35  65.00-150.00   56
 14  \w     70.00  97.00   0.50    0.20    --   41.35  32.00   0.00   54
 15  \w     25.00  67.00   0.50    0.20    --   41.35  65.00-150.00   84
 16  \w     29.00  99.00   0.50    0.20    --   41.35  43.00-150.00  140
 17  \w      4.00  43.00   0.50    0.20    --   41.35 -48.00 -32.00   78
 18  \w     35.00 106.00   0.50    0.66    --  101.00 -25.00  90.00  142
 19  \w     51.00 109.00   0.50    0.66    --  101.00 -33.00 150.00  116
 20  \w     79.00 106.00   0.50    0.66    --  101.00 -25.00 -90.00   54
 21  \w     89.00 141.00   0.50    0.66    --  101.00  42.00  60.00  104
 22  \w     88.00 154.00   0.50    0.66    --  101.00  50.00  90.00  132
 23  \w     35.00  77.00   0.50    0.66    --  101.00 -25.00 -90.00   84
 24  \w     61.00 127.00   0.50    0.66    --  101.00 -77.00 120.00  132
 25  \w    109.00 149.00   0.50    0.66    --  101.00 133.00 -30.00   80
 26  \w     93.00 157.00   0.50    0.66    --  101.00  25.00  30.00  128
 27  \w     95.00 151.00   0.50    0.66    --  101.00  17.00 -90.00  112
 28  \w     59.00  96.00   0.50    0.66    --  101.00 -50.00-180.00   74
 29  \w     57.00  85.00   0.50    0.66    --  101.00 -33.00-120.00   56
 30  \w     50.00 112.00   0.50    0.66    --  101.00 -50.00  90.00  124
 31  \w    111.00 148.00   0.50    0.66    --  101.00  33.00-180.00   74
 32  \w   -103.00 -76.00   0.50    0.20    --  -41.35 -48.00 -32.00   54
 33  \w    -59.00 -24.00   0.50    0.20    --  -41.35 -54.00-180.00   70
 34  \w      3.00  28.00   0.50    0.20    --  -41.35  21.00 -90.00   50
 35  \w    -37.00 -10.00   0.50    0.20    --  -41.35  21.00 -90.00   54
 36  \w     32.00  57.00   0.50    0.20    --   41.35  54.00 -90.00   50
 37  \w     67.00  96.00   0.50    0.20    --   41.35  54.00 -90.00   58
 38  \w     37.00  64.00   0.50    0.20    --   41.35  32.00-180.00   54
 39  \w     51.00  94.00   0.50    0.20    --   41.35-138.00  30.00   86
 40  \w     17.00  42.00   0.50    0.20    --   41.35  77.00-120.00   50
 41  \w     82.00 107.00   0.50    0.20    --   41.35  32.00-180.00   50
 42  \w    131.00 157.00   0.50    0.66    --  101.00  77.00-120.00   52
 43  \w     82.00 119.00   0.50    0.66    --  101.00  -8.00 120.00   74
 44  \w     77.00 102.00   0.50    0.66    --  101.00  77.00-120.00   50
 45  \w     80.00 110.00   0.50    0.66    --  101.00  68.00-120.00   60
 46  \w     86.00 111.00   0.50    0.66    --  101.00  50.00-180.00   50
 47  \w     84.00 115.00   0.50    0.66    --  101.00  59.00 150.00   62
 48  \w     29.00  56.00   0.50    0.66    --  101.00  -8.00 120.00   54
 49  \w     96.00 150.00   0.50    0.66    --  101.00  33.00 150.00  108
 50  \w    132.00 157.00   0.50    0.66    --  101.00  77.00-150.00   50
 51  \w    122.00 149.00   0.50    0.66    --  101.00  73.00 177.21   54
 52  \w     76.00 103.00   0.50    0.66    --  101.00  77.00-180.00   54
 53  \w     83.00 109.00   0.50    0.66    --  101.00  59.00-120.00   52
 54  \w     83.00 109.00   0.50    0.66    --  101.00  59.00-180.00   52
 55  \w     83.00 110.00   0.50    0.66    --  101.00  59.00 -90.00   54
 56  \w    124.00 151.00   0.50    0.66    --  101.00  77.00 150.00   54
 57  \w     76.00 112.00   0.50    0.66    --  101.00  77.00 150.00   72
 58  \w     76.00 102.00   0.50    0.66    --  101.00  77.00-150.00   52
 59  \w     41.00  97.00   0.50    0.66    --  101.00 -68.00 -60.00  112
 60  \w    131.00 157.00   0.50    0.66    --  101.00  50.00  60.00   52
 61  \w     89.00 116.00   0.50    0.66    --  101.00  50.00 -90.00   54
 62  \w    131.00 157.00   0.50    0.66    --  101.00  50.00-180.00   52
 63  \w     47.00 109.00   0.50    0.66    --  101.00 -25.00 -30.00  124
 64  \w     80.00 137.00   0.50    0.66    --  101.00  68.00 -90.00  114
 65  \w     78.00 104.00   0.50    0.66    --  101.00  73.00 177.21   52
 66  \w    132.00 157.00   0.50    0.66    --  101.00  59.00-150.00   50
 67  \w     37.00  62.00   0.50    0.66    --  101.00 -33.00 -60.00   50
 68  \w     81.00 110.00   0.50    0.66    --  101.00  63.00-132.73   58
 69  \w     80.00 110.00   0.50    0.66    --  101.00  68.00-150.00   60
 70  \w    113.00 140.00   0.50    0.66    --  101.00  33.00  30.00   54
 71  \w     86.00 142.00   0.50    0.66    --  101.00  50.00-150.00  112
 72  \w     84.00 111.00   0.50    0.66    --  101.00  59.00-150.00   54
;
_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      0.1124788000
_diffrn_orient_matrix_UB_12      -0.0365074000
_diffrn_orient_matrix_UB_13      -0.0332876000
_diffrn_orient_matrix_UB_21      -0.1123546000
_diffrn_orient_matrix_UB_22      -0.0323221000
_diffrn_orient_matrix_UB_23      -0.1441108000
_diffrn_orient_matrix_UB_31      0.0069985000
_diffrn_orient_matrix_UB_32      0.0669476000
_diffrn_orient_matrix_UB_33      -0.0878368000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19190
_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         69.993
_diffrn_reflns_theta_min         4.569
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96325
_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    1.309
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0620P)^2^+0.4831P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1107
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2977
_reflns_number_total             3388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00822e2.cif
_cod_data_source_block           7072-9921_avv873
_cod_database_code               1555062
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.784
_shelx_estimated_absorpt_t_min   0.710
_reflns_odcompleteness_completeness 100.00
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C9(H9), C13(H13), C18(H18), C20(H20), C14(H14), C21(H21), C8(H8),
 C15(H15), C16(H16), C6(H6), C22(H22), C12(H12)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              20589
_shelx_hkl_checksum              19377
_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 1.153
_oxdiff_exptl_absorpt_empirical_full_min 0.886