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_1555065
_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'
_chemical_formula_sum            'C24 H21 F3'
_chemical_formula_weight         366.41
_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                92.410(3)
_cell_angle_beta                 96.248(4)
_cell_angle_gamma                107.450(4)
_cell_formula_units_Z            4
_cell_length_a                   9.7671(5)
_cell_length_b                   10.3099(4)
_cell_length_c                   19.8876(7)
_cell_measurement_reflns_used    6044
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3420
_cell_measurement_theta_min      3.0420
_cell_volume                     1893.23(15)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -42.00   45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  -57.0000  120.0000 87

  2 omega   54.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558 -133.0000   42.0000 33

  3 omega   48.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  178.0000  150.0000 50

  4 omega   54.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558 -136.0000 -135.0000 34

  5 omega    5.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   57.0000    0.0000 85

  6 omega   74.00  100.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  178.0000  -30.0000 26

  7 omega   19.00   44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   57.0000 -150.0000 25

  8 omega  -49.00   57.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  -19.0000 -180.0000 106

  9 omega   12.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   57.0000  -90.0000 81

 10 omega   51.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  178.0000   60.0000 45

 11 omega   -6.00   59.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   77.0000   90.0000 65
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0762012000
_diffrn_orient_matrix_UB_12      -0.0262208000
_diffrn_orient_matrix_UB_13      -0.0083031000
_diffrn_orient_matrix_UB_21      0.0080706000
_diffrn_orient_matrix_UB_22      -0.0004461000
_diffrn_orient_matrix_UB_23      -0.0350169000
_diffrn_orient_matrix_UB_31      0.0043385000
_diffrn_orient_matrix_UB_32      -0.0674209000
_diffrn_orient_matrix_UB_33      0.0004198000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24129
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.682
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.285
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.51
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.049
_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     491
_refine_ls_number_reflns         8686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0469P)^2^+1.3111P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6685
_reflns_number_total             8686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00822e2.cif
_cod_data_source_block           7072-9921_emt078
_cod_original_cell_volume        1893.23(14)
_cod_database_code               1555065
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'F3 C20'
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.946
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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), C4B(H4B)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C3B(H3BA,H3BB)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C15(H15), C6B(H6B), C14(H14), C20(H20), C19B(H19B),
 C8B(H8B), C17(H17), C22B(H22D), C21(H21), C12(H12), C9B(H9B), C6(H6), C9(H9),
 C18B(H18B), C18(H18), C21B(H21B), C8(H8), C14B(H14B), C16B(H16B), C12B(H12B),
 C15B(H15B), C13B(H13B)
2.d Idealised Me refined as rotating group:
 C23B(H23D,H23E,H23F), C24B(H24A,H24B,H24C), C23(H23A,H23B,H23C), C22(H22A,
 H22B,H22C)
;
_shelx_res_checksum              97797
_shelx_hkl_checksum              70371
_olex2_submission_special_instructions 'No special instructions were received'