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_1553582
_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         'C20 H20 Br F3 O2'
_chemical_formula_sum            'C20 H20 Br F3 O2'
_chemical_formula_weight         429.27
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-21
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  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
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_audit_update_record
;
2015-07-15 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                100.216(4)
_cell_angle_beta                 97.306(5)
_cell_angle_gamma                100.289(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3533(5)
_cell_length_b                   9.4941(4)
_cell_length_c                   12.1934(7)
_cell_measurement_reflns_used    4567
_cell_measurement_temperature    105(8)
_cell_measurement_theta_max      28.9480
_cell_measurement_theta_min      3.0580
_cell_volume                     923.70(9)
_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
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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
;
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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      105(8)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_measurement_details
;
  1 omega  -62.00  -36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777 -178.0000   30.0000 26

  2 omega  -90.00  -46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -38.0000 -120.0000 44

  3 omega   -5.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000   60.0000 29

  4 omega  -16.00   17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000    0.0000 33

  5 omega  -20.00   18.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000 -180.0000 38

  6 omega  -94.00  -42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777 -178.0000  -60.0000 52

  7 omega   -2.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000  -30.0000 88

  8 omega   55.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  178.0000 -150.0000 40

  9 omega  -15.00   79.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   19.0000  -90.0000 94

 10 omega  -25.00   60.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -99.0000  -30.0000 85

 11 omega   34.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -99.0000  120.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0638978000
_diffrn_orient_matrix_UB_12      -0.0177861000
_diffrn_orient_matrix_UB_13      -0.0295853000
_diffrn_orient_matrix_UB_21      0.0557133000
_diffrn_orient_matrix_UB_22      0.0169671000
_diffrn_orient_matrix_UB_23      0.0517441000
_diffrn_orient_matrix_UB_31      -0.0216076000
_diffrn_orient_matrix_UB_32      -0.0735808000
_diffrn_orient_matrix_UB_33      0.0061321000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10460
_diffrn_reflns_theta_full        28.94
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82160
_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    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0268P)^2^+0.3223P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0651
_reflns_number_gt                3711
_reflns_number_total             4114
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00643d4.cif
_cod_data_source_block           a283
_cod_original_cell_volume        923.70(8)
_cod_database_code               1553582
_chemical_oxdiff_formula         'C20 H20 F3 Br1 O2'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32