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_1555076
_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         'C25 H23 F3 O2'
_chemical_formula_sum            'C25 H23 F3 O2'
_chemical_formula_weight         412.43
_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     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                90
_cell_angle_beta                 105.635(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.5733(2)
_cell_length_b                   18.7290(4)
_cell_length_c                   19.4741(4)
_cell_measurement_reflns_used    20069
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.7690
_cell_measurement_theta_min      3.9070
_cell_volume                     4064.94(14)
_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 0.996
_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    -31.00  13.00   0.50    0.20    --  -41.22 106.00  -9.00   88
  2  \w    -75.00 -37.00   0.50    0.20    --  -41.22 106.00  -9.00   76
  3  \w     82.00 154.00   0.50    0.45    --  101.00 106.00  -9.00  144
  4  \w     54.00 100.00   0.50    0.45    --  101.00-106.00-108.00   92
  5  \w    -55.00 -13.00   0.50    0.20    --  -41.22 138.00-120.00   84
  6  \w    -41.00   5.00   0.50    0.20    --  -41.22  43.00   0.00   92
  7  \w    -91.00 -65.00   0.50    0.20    --  -41.22 138.00-120.00   52
  8  \w   -103.00 -33.00   0.50    0.20    --  -41.22 -32.00-150.00  140
  9  \w    -95.00 -35.00   0.50    0.20    --  -41.22 -32.00 120.00  120
 10  \w    -58.00  13.00   0.50    0.20    --  -41.22  54.00-150.00  142
 11  \w     31.00  56.00   0.50    0.20    --   41.22  43.00  30.00   50
 12  \w     65.00  97.00   0.50    0.20    --   41.22  43.00  30.00   64
 13  \w     23.00 101.00   0.50    0.20    --   41.22  65.00 -30.00  156
 14  \w    -13.00  17.00   0.50    0.20    --   41.22-104.00-150.00   60
 15  \w    -16.00  25.00   0.50    0.20    --   41.22 -32.00  90.00   82
 16  \w     22.00  47.00   0.50    0.20    --   41.22-106.00-108.00   50
 17  \w     29.00  54.00   0.50    0.20    --   41.22  43.00  60.00   50
 18  \w     25.00  71.00   0.50    0.20    --   41.22-104.00-150.00   92
 19  \w     45.00 109.00   0.50    0.45    --  101.00 -25.00-120.00  128
 20  \w     86.00 120.00   0.50    0.45    --  101.00 -59.00 -90.00   68
 21  \w     37.00 119.00   0.50    0.45    --  101.00 -77.00-120.00  164
 22  \w     53.00 109.00   0.50    0.45    --  101.00 -33.00-180.00  112
 23  \w     98.00 123.00   0.50    0.45    --  101.00 -68.00   0.00   50
 24  \w     93.00 123.00   0.50    0.45    --  101.00 -87.00 -90.00   60
 25  \w    116.00 141.00   0.50    0.45    --  101.00  33.00 -30.00   50
 26  \w     53.00  79.00   0.50    0.45    --  101.00 -87.00 -90.00   52
 27  \w     92.00 157.00   0.50    0.45    --  101.00  25.00 -90.00  130
 28  \w     37.00 110.00   0.50    0.45    --  101.00 -33.00   0.00  146
 29  \w     31.00 108.00   0.50    0.45    --  101.00 -17.00   0.00  154
 30  \w     53.00  79.00   0.50    0.45    --  101.00 -59.00 -90.00   52
 31  \w     39.00 113.00   0.50    0.45    --  101.00 -50.00  90.00  148
 32  \w     85.00 157.00   0.50    0.45    --  101.00  68.00-180.00  144
 33  \w     88.00 114.00   0.50    0.45    --  101.00-111.00 -60.00   52
 34  \w     35.00 127.00   0.50    0.45    --  101.00 -93.00  60.00  184
 35  \w     33.00  59.00   0.50    0.20    --   41.22-106.00-108.00   52
 36  \w    -50.00 -25.00   0.50    0.20    --  -41.22  21.00 -30.00   50
 37  \w    -87.00 -37.00   0.50    0.20    --  -41.22 -32.00 150.00  100
 38  \w     82.00 107.00   0.50    0.20    --   41.22  32.00 -60.00   50
 39  \w     24.00  49.00   0.50    0.20    --   41.22 -32.00 -90.00   50
 40  \w     34.00  59.00   0.50    0.20    --   41.22 -54.00-150.00   50
 41  \w    -23.00   3.00   0.50    0.20    --   41.22 -32.00 -90.00   52
 42  \w     -4.00  49.00   0.50    0.20    --   41.22 -32.00-180.00  106
 43  \w     43.00  69.00   0.50    0.20    --   41.22  32.00  90.00   52
 44  \w     99.00 146.00   0.50    0.45    --  101.00  50.00-150.00   94
 45  \w     77.00 124.00   0.50    0.45    --  101.00  77.00 150.00   94
 46  \w     93.00 118.00   0.50    0.45    --  101.00 -68.00 -30.00   50
 47  \w    130.00 155.00   0.50    0.45    --  101.00  77.00 150.00   50
 48  \w     51.00 121.00   0.50    0.45    --  101.00-133.00  90.00  140
 49  \w     51.00 109.00   0.50    0.45    --  101.00-111.00-120.00  116
 50  \w    101.00 156.00   0.50    0.45    --  101.00  25.00 150.00  110
 51  \w     39.00 119.00   0.50    0.45    --  101.00 -77.00  90.00  160
 52  \w     89.00 114.00   0.50    0.45    --  101.00 -17.00-120.00   50
 53  \w     88.00 124.00   0.50    0.45    --  101.00-133.00-120.00   72
 54  \w     64.00 104.00   0.50    0.45    --  101.00 -42.00 -90.00   80
;
_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      0.0963501000
_diffrn_orient_matrix_UB_12      -0.0408592000
_diffrn_orient_matrix_UB_13      -0.0254265000
_diffrn_orient_matrix_UB_21      0.0291614000
_diffrn_orient_matrix_UB_22      0.0683790000
_diffrn_orient_matrix_UB_23      -0.0360656000
_diffrn_orient_matrix_UB_31      0.0947591000
_diffrn_orient_matrix_UB_32      0.0205458000
_diffrn_orient_matrix_UB_33      0.0692708000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38593
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.049
_diffrn_reflns_theta_min         3.335
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95796
_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    1.348
_exptl_crystal_description       prism
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.040
_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     547
_refine_ls_number_reflns         7965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0442P)^2^+1.0699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7021
_reflns_number_total             7965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00822e2.cif
_cod_data_source_block           7072-9926_b-45
_cod_original_cell_volume        4064.92(15)
_cod_database_code               1555076
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.759
_shelx_estimated_absorpt_t_min   0.720
_reflns_odcompleteness_completeness 99.96
_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:
 C31(H31), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C47(H47), C20(H20), C51(H51), C8(H8), C5(H5), C17(H17), C6(H6),
 C38(H38), C45(H45), C11(H11), C44(H44), C50(H50), C41(H41), C14(H14), C12(H12),
  C15(H15), C35(H35), C43(H43), C42(H42), C36(H36), C13(H13)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C55(H55A,H55B,H55C), C25(H25A,H25B,H25C), C60(H60A,H60B,
 H60C), C53(H53A,H53B,H53C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              75995
_shelx_hkl_checksum              79332
_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 1.174
_oxdiff_exptl_absorpt_empirical_full_min 0.755