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_1555064
_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 F4 O2'
_chemical_formula_sum            'C24 H20 F4 O2'
_chemical_formula_weight         416.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 94.8210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.76460(10)
_cell_length_b                   10.6788(2)
_cell_length_c                   20.8962(3)
_cell_measurement_reflns_used    7288
_cell_measurement_temperature    100(3)
_cell_measurement_theta_max      71.4460
_cell_measurement_theta_min      4.1210
_cell_volume                     1948.87(5)
_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(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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    -99.00 -24.00   0.50    0.20    --  -41.22 -69.00-143.00  150
  2  \w    -32.00  -6.00   0.50    0.20    --  -41.22  69.00 -11.00   52
  3  \w     58.00 105.00   0.50    0.20    --   41.22  69.00 -11.00   94
  4  \w     20.00  55.00   0.50    0.20    --   41.22 -69.00-143.00   70
  5  \w     95.00 150.00   0.50    0.20    --  101.00  69.00 -11.00  110
  6  \w     69.00 120.00   0.50    0.20    --  101.00 -69.00-143.00  102
  7  \w    -49.00 -21.00   0.50    0.20    --  -41.22  21.00   0.00   56
  8  \w   -107.00 -33.00   0.50    0.20    --  -41.22 -32.00 120.00  148
  9  \w    -15.00  27.00   0.50    0.20    --  -41.22  21.00   0.00   84
 10  \w    -48.00  -9.00   0.50    0.20    --  -41.22  43.00-120.00   78
 11  \w    -25.00  24.00   0.50    0.20    --  -41.22  32.00 120.00   98
 12  \w     37.00 107.00   0.50    0.20    --   41.22  21.00 120.00  140
 13  \w     82.00 107.00   0.50    0.20    --   41.22  32.00 -30.00   50
 14  \w     24.00  53.00   0.50    0.20    --   41.22 -43.00 120.00   58
 15  \w    -19.00   9.00   0.50    0.20    --   41.22 -43.00 120.00   56
 16  \w    -16.00  58.00   0.50    0.20    --   41.22 -54.00-120.00  148
 17  \w     82.00 149.00   0.50    0.20    --  101.00  68.00 -60.00  134
 18  \w    109.00 152.00   0.50    0.20    --  101.00  93.00 -90.00   86
 19  \w     99.00 155.00   0.50    0.20    --  101.00  93.00 -60.00  112
 20  \w     44.00  97.00   0.50    0.20    --  101.00 -42.00 -90.00  106
 21  \w     40.00  98.00   0.50    0.20    --  101.00 -33.00 150.00  116
 22  \w     52.00 111.00   0.50    0.20    --  101.00 -50.00-180.00  118
 23  \w     90.00 155.00   0.50    0.20    --  101.00  50.00  30.00  130
 24  \w     56.00  82.00   0.50    0.20    --  101.00-133.00-180.00   52
 25  \w     89.00 117.00   0.50    0.20    --  101.00-133.00-180.00   56
 26  \w    113.00 147.00   0.50    0.20    --  101.00  17.00 -90.00   68
 27  \w     38.00 114.00   0.50    0.20    --  101.00 -42.00  30.00  152
 28  \w     97.00 125.00   0.50    0.20    --  101.00  33.00-180.00   56
 29  \w     49.00 109.00   0.50    0.20    --  101.00 -25.00-180.00  120
 30  \w     35.00 106.00   0.50    0.20    --  101.00 -17.00   0.00  142
 31  \w     94.00 119.00   0.50    0.20    --  101.00  69.00 -11.00   50
 32  \w    -51.00 -22.00   0.50    0.20    --  -41.22 -65.00  60.00   58
 33  \w    -92.00 -66.00   0.50    0.20    --  -41.22 -65.00  60.00   52
 34  \w    -90.00 -60.00   0.50    0.20    --  -41.22 -21.00 -90.00   60
 35  \w     80.00  86.50   0.50    0.20    --   41.22  65.00 150.00   13
;
_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      -0.0482492000
_diffrn_orient_matrix_UB_12      0.0249149000
_diffrn_orient_matrix_UB_13      -0.0714562000
_diffrn_orient_matrix_UB_21      0.1000578000
_diffrn_orient_matrix_UB_22      -0.1104608000
_diffrn_orient_matrix_UB_23      -0.0188370000
_diffrn_orient_matrix_UB_31      -0.1371450000
_diffrn_orient_matrix_UB_32      -0.0893015000
_diffrn_orient_matrix_UB_33      0.0033741000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11506
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.277
_diffrn_reflns_theta_min         4.247
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.979
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73863
_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    1.419
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0556P)^2^+0.3381P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3377
_reflns_number_total             3803
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00822e2.cif
_cod_data_source_block           9926_emt074
_cod_database_code               1555064
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C30 F3'
_shelx_estimated_absorpt_t_max   0.843
_shelx_estimated_absorpt_t_min   0.828
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.55
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C14(H14), C25(H25), C6(H6), C21(H21), C15(H15), C5(H5),
 C24(H24), C23(H23), C22(H22)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              29764
_shelx_hkl_checksum              7507
_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.713