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_1555066
_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 O2'
_chemical_formula_sum            'C24 H21 F3 O2'
_chemical_formula_weight         398.41
_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             2018-10-23
_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                98.214(9)
_cell_angle_beta                 105.322(9)
_cell_angle_gamma                103.258(9)
_cell_formula_units_Z            2
_cell_length_a                   8.8501(9)
_cell_length_b                   10.1181(12)
_cell_length_c                   11.7209(10)
_cell_measurement_reflns_used    1895
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.5790
_cell_measurement_theta_min      3.9410
_cell_volume                     961.85(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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.969
_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 -38.00   0.50    8.00    --  -41.22 -39.00 -84.00  128
  2  \w    -18.00  30.00   0.50    8.00    --   41.22 -39.00 -84.00   96
  3  \w     32.00  69.00   0.50    8.00    --   41.22  39.00  70.00   74
  4  \w     71.00 102.00   0.50    8.00    --   41.22  39.00  70.00   62
  5  \w     89.00 153.00   0.50   20.00    --  100.29  39.00  70.00  128
  6  \w     38.00 111.00   0.50   20.00    --  100.29 -39.00 -84.00  146
  7  \w    -96.00 -31.00   0.50    8.00    --  -41.22 138.00-150.00  130
  8  \w    -95.00 -24.00   0.50    8.00    --  -41.22 -54.00  90.00  142
  9  \w    -14.00  18.00   0.50    8.00    --  -41.22  32.00-150.00   64
 10  \w    -61.00  23.00   0.50    8.00    --  -41.22  65.00-120.00  168
 11  \w    -72.00 -43.00   0.50    8.00    --  -41.22 138.00  60.00   58
 12  \w    -45.00 -20.00   0.50    8.00    --  -41.22  32.00-150.00   50
 13  \w   -100.00 -62.00   0.50    8.00    --  -41.22 -32.00   0.00   76
 14  \w    -50.00   2.00   0.50    8.00    --  -41.22  39.00  70.00  104
 15  \w    -36.00 -11.00   0.50    8.00    --  -41.22 138.00  60.00   50
 16  \w    -29.00  11.00   0.50    8.00    --   41.22 -11.00 120.00   80
 17  \w     24.00  65.00   0.50    8.00    --   41.22 -11.00 120.00   82
 18  \w     32.00  78.00   0.50    8.00    --   41.22-138.00 150.00   92
 19  \w     34.00  94.00   0.50    8.00    --   41.22-138.00  60.00  120
 20  \w     -5.00  35.00   0.50    8.00    --   41.22 -65.00 -90.00   80
 21  \w     36.00  63.00   0.50    8.00    --   41.22  32.00-120.00   54
 22  \w     92.00 156.00   0.50   20.00    --  100.29  25.00  60.00  128
 23  \w     70.00 117.00   0.50   20.00    --  100.29-117.00-120.00   94
 24  \w     83.00 112.00   0.50   20.00    --  100.29 -42.00   0.00   58
 25  \w     92.00 129.00   0.50   20.00    --  100.29  25.00 120.00   74
 26  \w     57.00 108.00   0.50   20.00    --  100.29 -42.00 150.00  102
 27  \w    106.00 131.00   0.50   20.00    --  100.29-145.00 -60.00   50
 28  \w     81.00 108.00   0.50   20.00    --  100.29 -96.00 -60.00   54
 29  \w     83.00 110.00   0.50   20.00    --  100.29-117.00  60.00   54
 30  \w     91.00 147.00   0.50   20.00    --  100.29  17.00 -30.00  112
 31  \w     88.00 114.00   0.50   20.00    --  100.29  17.00-120.00   52
 32  \w     80.00 105.00   0.50   20.00    --  100.29  77.00   0.00   50
 33  \w     42.00 115.00   0.50   20.00    --  100.29 -77.00 -30.00  146
 34  \w     38.00  63.00   0.50   20.00    --  100.29-145.00 -60.00   50
 35  \w     85.00 111.00   0.50   20.00    --  100.29-117.00-180.00   52
 36  \w     58.00 109.00   0.50   20.00    --  100.29 -50.00-150.00  102
 37  \w     40.00 125.00   0.50   20.00    --  100.29 -77.00-150.00  170
 38  \w     35.00  86.00   0.50   20.00    --  100.29 -25.00-150.00  102
 39  \w    129.00 156.00   0.50   20.00    --  100.29  59.00 120.00   54
 40  \w     97.00 124.00   0.50   20.00    --  100.29  59.00 120.00   54
 41  \w     95.00 129.00   0.50   20.00    --  100.29-145.00  30.00   68
 42  \w     33.00 106.00   0.50   20.00    --  100.29 -96.00  90.00  146
 43  \w     56.00 116.00   0.50   20.00    --  100.29 -50.00 -30.00  120
 44  \w     37.00 111.00   0.50   20.00    --  100.29 -42.00  90.00  148
 45  \w     88.00 107.50   0.50   20.00    --  100.29  17.00  30.00   39
;
_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      -0.0306810000
_diffrn_orient_matrix_UB_12      -0.1165001000
_diffrn_orient_matrix_UB_13      0.0695061000
_diffrn_orient_matrix_UB_21      -0.1701361000
_diffrn_orient_matrix_UB_22      0.0185648000
_diffrn_orient_matrix_UB_23      -0.0076616000
_diffrn_orient_matrix_UB_31      -0.0740979000
_diffrn_orient_matrix_UB_32      -0.1085496000
_diffrn_orient_matrix_UB_33      -0.1206656000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6591
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.973
_diffrn_reflns_theta_min         4.006
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70070
_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    1.376
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         6591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0868
_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^)+(0.1785P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2319
_refine_ls_wR_factor_ref         0.2604
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4435
_reflns_number_total             6591
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9090\% 
 around [0.92 -0.23 -0.32] (reciprocal) or [1.00 0.01 0.00] (direct)
;
_cod_data_source_file            c9qo00822e2.cif
_cod_data_source_block           7072-10064_b38_ab_twin1_hklf4
_cod_original_cell_volume        961.86(18)
_cod_database_code               1555066
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 F3'
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.916
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.707(2)
 0.293(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C20(H20), C16(H16), C6(H6), C9(H9), C13(H13), C21(H21),
 C12(H12), C18(H18), C14(H14), C22(H22)
3.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              14719
_shelx_hkl_checksum              86041
_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 2.934
_oxdiff_exptl_absorpt_empirical_full_min 0.448
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2