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_1555069
_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 H20 Cl F3 O2'
_chemical_formula_sum            'C24 H20 Cl F3 O2'
_chemical_formula_weight         432.85
_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             2018-10-23
_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                77.527(4)
_cell_angle_beta                 82.086(4)
_cell_angle_gamma                74.544(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0216(4)
_cell_length_b                   9.9831(4)
_cell_length_c                   11.9107(5)
_cell_measurement_reflns_used    5511
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6870
_cell_measurement_theta_min      3.7860
_cell_volume                     1005.86(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -81.00 -56.00   0.50    0.20    --  -41.22 112.00 164.00   50
  2  \w    -19.00   8.00   0.50    0.20    --  -41.22 112.00 164.00   54
  3  \w    -48.00 -21.00   0.50    0.20    --  -41.22 112.00 164.00   54
  4  \w     93.00 142.00   0.50    0.20    --  101.00 112.00 164.00   98
  5  \w   -101.00 -30.00   0.50    0.20    --  -41.22 -43.00  90.00  142
  6  \w   -102.00 -61.00   0.50    0.20    --  -41.22 -65.00   0.00   82
  7  \w    -54.00 -23.00   0.50    0.20    --  -41.22 -65.00   0.00   62
  8  \w    -91.00 -16.00   0.50    0.20    --  -41.22 -77.00  60.00  150
  9  \w    -83.00 -50.00   0.50    0.20    --  -41.22 138.00  60.00   66
 10  \w   -102.00 -33.00   0.50    0.20    --  -41.22 -32.00-150.00  138
 11  \w    -38.00  20.00   0.50    0.20    --  -41.22  43.00-150.00  116
 12  \w     12.00  97.00   0.50    0.20    --   41.22-138.00   0.00  170
 13  \w      0.00  26.00   0.50    0.20    --   41.22 -21.00 -90.00   52
 14  \w     25.00  59.00   0.50    0.20    --   41.22 -65.00-150.00   68
 15  \w    -18.00   7.00   0.50    0.20    --   41.22 -65.00-150.00   50
 16  \w     58.00  87.00   0.50    0.20    --   41.22-138.00  60.00   58
 17  \w     -6.00  21.00   0.50    0.20    --   41.22-112.00  70.00   54
 18  \w     43.00  68.00   0.50    0.20    --   41.22-112.00  70.00   50
 19  \w     18.00  53.00   0.50    0.20    --   41.22 -43.00  60.00   70
 20  \w      5.00  39.00   0.50    0.20    --   41.22 -32.00 -60.00   68
 21  \w     61.00 104.00   0.50    0.20    --   41.22  32.00 -60.00   86
 22  \w    -11.00  15.00   0.50    0.20    --   41.22 -43.00  60.00   52
 23  \w     93.00 153.00   0.50    0.20    --  101.00  33.00 120.00  120
 24  \w     36.00  88.00   0.50    0.20    --  101.00-111.00-150.00  104
 25  \w     61.00 127.00   0.50    0.20    --  101.00 -77.00-150.00  132
 26  \w     72.00 121.00   0.50    0.20    --  101.00-133.00-150.00   98
 27  \w    127.00 153.00   0.50    0.20    --  101.00  77.00 150.00   52
 28  \w     81.00 155.00   0.50    0.20    --  101.00  68.00-150.00  148
 29  \w     39.00 113.00   0.50    0.20    --  101.00 -42.00  30.00  148
 30  \w     77.00 102.00   0.50    0.20    --  101.00  77.00 150.00   50
 31  \w     45.00  71.00   0.50    0.20    --  101.00 -77.00 -90.00   52
 32  \w     79.00 115.00   0.50    0.20    --  101.00 -77.00 -90.00   72
 33  \w    101.00 155.00   0.50    0.20    --  101.00  33.00 -90.00  108
 34  \w     94.00 130.00   0.50    0.20    --  101.00  42.00 150.00   72
 35  \w     89.00 115.00   0.50    0.20    --  101.00-111.00 -30.00   52
 36  \w    118.00 144.00   0.50    0.20    --  101.00 133.00 120.00   52
 37  \w     42.00  67.00   0.50    0.20    --  101.00-111.00 -30.00   50
 38  \w     87.00 112.00   0.50    0.20    --  101.00-111.00  90.00   50
 39  \w     38.00  93.00   0.50    0.20    --  101.00 -77.00  90.00  110
 40  \w     75.00 109.00   0.50    0.20    --  101.00 -33.00-180.00   68
 41  \w     35.00  83.00   0.50    0.20    --  101.00-111.00  90.00   96
 42  \w     86.00 156.00   0.50    0.20    --  101.00  68.00 -30.00  140
 43  \w     75.00 122.00   0.50    0.20    --  101.00 -68.00  30.00   94
 44  \w     35.00 114.00   0.50    0.20    --  101.00-111.00-120.00  158
 45  \w     92.00 141.00   0.50    0.20    --  101.00  17.00  90.00   98
 46  \w     40.00 113.00   0.50    0.20    --  101.00 -42.00 -90.00  146
 47  \w     64.00 116.00   0.50    0.20    --  101.00 -59.00 -60.00  104
 48  \w     96.00 145.00   0.50    0.20    --  101.00  33.00-180.00   98
 49  \w     46.00 113.00   0.50    0.20    --  101.00 -50.00 150.00  134
 50  \w     97.00 141.00   0.50    0.20    --  101.00 178.00 120.00   88
 51  \w     93.00 146.00   0.50    0.20    --  101.00  33.00 -30.00  106
 52  \w     95.00 120.00   0.50    0.20    --  101.00  33.00 -60.00   50
 53  \w     40.00  65.00   0.50    0.20    --  101.00 -33.00-180.00   50
 54  \w     75.00  97.50   0.50    0.20    --  101.00-112.00  70.00   45
;
_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      0.1492724000
_diffrn_orient_matrix_UB_12      -0.0341266000
_diffrn_orient_matrix_UB_13      0.0608937000
_diffrn_orient_matrix_UB_21      0.0864694000
_diffrn_orient_matrix_UB_22      0.0519899000
_diffrn_orient_matrix_UB_23      -0.1151728000
_diffrn_orient_matrix_UB_31      -0.0431229000
_diffrn_orient_matrix_UB_32      0.1506791000
_diffrn_orient_matrix_UB_33      0.0265195000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9416
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_min         3.815
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95456
_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    1.429
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0453P)^2^+0.6162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3457
_reflns_number_total             3799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00822e2.cif
_cod_data_source_block           7072-9921_emt048
_cod_database_code               1555069
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'F3 C20'
_shelx_estimated_absorpt_t_max   0.563
_shelx_estimated_absorpt_t_min   0.415
_reflns_odcompleteness_completeness 99.74
_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:
 C12(H12), C9(H9), C6(H6), C13(H13), C16(H16), C21(H21), C22(H22), C14(H14),
 C15(H15), C19(H19), C18(H18)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              53934
_shelx_hkl_checksum              93122
_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 1.119
_oxdiff_exptl_absorpt_empirical_full_min 0.927