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_1553586
_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         'C19 H17 Br Cl F3'
_chemical_formula_sum            'C19 H17 Br Cl F3'
_chemical_formula_weight         417.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-21
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2016-08-10 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.447(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2233(3)
_cell_length_b                   22.8182(7)
_cell_length_c                   10.0565(3)
_cell_measurement_reflns_used    4710
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.5300
_cell_measurement_theta_min      2.8990
_cell_volume                     1779.36(11)
_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
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.8688
_diffrn_measurement_details
;
  1 omega  -77.00   -3.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -77.0000   30.0000 74

  2 omega  -48.00   -7.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000 -120.0000 41

  3 omega   70.00   95.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  178.0000   30.0000 25

  4 omega  -26.00   49.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -77.0000  150.0000 75

  5 omega  -90.00  -63.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -38.0000 -150.0000 27

  6 omega   -6.00   23.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  -90.0000 29

  7 omega  -36.00   -8.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -38.0000 -150.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0449597000
_diffrn_orient_matrix_UB_12      0.0246723000
_diffrn_orient_matrix_UB_13      0.0129871000
_diffrn_orient_matrix_UB_21      0.0204133000
_diffrn_orient_matrix_UB_22      -0.0087924000
_diffrn_orient_matrix_UB_23      0.0713490000
_diffrn_orient_matrix_UB_31      0.0770362000
_diffrn_orient_matrix_UB_32      0.0167374000
_diffrn_orient_matrix_UB_33      0.0182957000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10596
_diffrn_reflns_theta_full        28.53
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.63
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.487
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87103
_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    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0290P)^2^+0.5907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0631
_reflns_number_gt                3444
_reflns_number_total             3970
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00643d4.cif
_cod_data_source_block           a259
_cod_original_cell_volume        1779.35(11)
_cod_database_code               1553586
_chemical_oxdiff_formula         'C19 H17 F3 Cl1 Br1'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32