Brominated CF3-allyl alcohols as multicentered electrophiles in TfOH promoted reactions with arenes
Kazakova, Anna N.; Iakovenko, Roman O.; Boyarskaya, Irina A.; Ivanov, Alexander Yu.; Avdontceva, Margarita S.; Zolotarev, Andrei A.; Panikorovsky, Taras L.; Starova, Galina L.; Nenajdenko, Valentine G.; Vasilyev, Aleksander V.; Organic Chemistry Frontiers 4 (2017) 255–; doi:10.1039/C6QO00643D

data_1553583
_publ_section_title
;
 Brominated CF3-allyl alcohols as multicentered electrophiles in TfOH
 promoted reactions with arenes
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              255
_journal_paper_doi               10.1039/C6QO00643D
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C18 H15 Br2 F3'
_chemical_formula_sum            'C18 H15 Br2 F3'
_chemical_formula_weight         448.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-24
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2015-08-12 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.4974(2)
_cell_length_b                   6.84171(10)
_cell_length_c                   28.6498(3)
_cell_measurement_reflns_used    17306
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1100
_cell_measurement_theta_min      4.0690
_cell_volume                     3233.72(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9964
_diffrn_measurement_details
;
  1 omega  -62.00   34.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   57.0000  150.0000 96

  2 omega  -31.00   22.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -150.0000 53

  3 omega   59.00  112.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  -90.0000 53

  4 omega   69.00   94.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 25

  5 omega   36.00   89.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 53

  6 omega  106.00  132.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 26

  7 omega   53.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 34

  8 omega   58.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 27

  9 omega  120.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 58

 10 omega   88.00  113.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 25

 11 omega   39.00   81.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 42

 12 omega   87.00  112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 25

 13 omega   35.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 56

 14 omega   39.00   76.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 37

 15 omega   46.00   72.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 26

 16 omega   48.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 25

 17 omega   37.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 26

 18 omega   29.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 34

 19 omega   38.00   63.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   73.0000  -44.0000 25

 20 omega -116.00  -27.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000   30.0000 89

 21 omega  -44.00   32.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -30.0000 76

 22 omega   56.00  128.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000    0.0000 72

 23 omega   62.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -90.0000 27

 24 omega   85.00  119.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  120.0000 34

 25 omega   80.00  110.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 30

 26 omega  134.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 42

 27 omega   83.00  158.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  120.0000 75

 28 omega  142.00  168.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   90.0000 26

 29 omega   53.00   79.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 26

 30 omega   43.00   78.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 35

 31 omega   82.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 33

 32 omega  129.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 48

 33 omega  102.00  136.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 34

 34 omega  114.00  154.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -30.0000 40

 35 omega   89.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 26

 36 omega  116.00  141.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   90.0000 25

 37 omega  119.00  145.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 26

 38 omega   60.00   86.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 26

 39 omega   87.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   90.0000 44

 40 omega  107.00  149.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 42

 41 omega   85.00  110.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 25

 42 omega  121.00  155.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 34

 43 omega  106.00  132.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 26

 44 omega  153.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 25

 45 omega   86.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 25

 46 omega  116.00  142.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -90.0000 26

 47 omega   80.00  105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 25

 48 omega  153.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 25

 49 omega  100.00  126.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 26

 50 omega   90.00  170.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 80

 51 omega  110.00  136.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 26

 52 omega   67.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 26

 53 omega   73.00   99.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   90.0000 26

 54 omega   59.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 38

 55 omega   33.00   65.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  150.0000 32

 56 omega  143.00  169.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  150.0000 26

 57 omega   57.00   86.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -27.0000   -6.4743 29

 58 omega   90.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 26

 59 omega   42.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 35

 60 omega   81.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 27

 61 omega   58.00   84.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 26

 62 omega   35.00  102.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 67
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0250997000
_diffrn_orient_matrix_UB_12      0.1035756000
_diffrn_orient_matrix_UB_13      0.0455123000
_diffrn_orient_matrix_UB_21      -0.0715044000
_diffrn_orient_matrix_UB_22      0.0971388000
_diffrn_orient_matrix_UB_23      -0.0256719000
_diffrn_orient_matrix_UB_31      -0.0545549000
_diffrn_orient_matrix_UB_32      -0.1747751000
_diffrn_orient_matrix_UB_33      0.0126868000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            38981
_diffrn_reflns_theta_full        72.49
_diffrn_reflns_theta_max         72.49
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60598
_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            colorless
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tables
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+0.9051P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0612
_reflns_number_gt                2961
_reflns_number_total             3212
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00643d4.cif
_cod_data_source_block           a174
_cod_original_cell_volume        3233.71(7)
_cod_database_code               1553583
_chemical_oxdiff_formula         'C18 H15 f3 br2'
_reflns_odcompleteness_completeness 95.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95