Friedel-Crafts Alkylation of Arenes with 2-Halogeno-2-CF3-styrenes under Superacidic Conditions. Access to Trifluoromethylated Ethanes and Ethenes.
Sandzhieva, Maria A.; Kazakova, Anna N.; Boyarskaya, Irina A.; Ivanov, Alexandr Yu; Nenajdenko, Valentine G.; Vasilyev, Aleksander V.; The Journal of organic chemistry 81 (2016) 5032–5045; doi:10.1021/acs.joc.6b00419

data_4036762
_publ_section_title
;
 Friedel-Crafts Alkylation of Arenes with 2-Halogeno-2-CF3-styrenes under
 Superacidic Conditions. Access to Trifluoromethylated Ethanes and
 Ethenes.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5032
_journal_page_last               5045
_journal_paper_doi               10.1021/acs.joc.6b00419
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C19 H20 Br F3'
_chemical_formula_sum            'C19 H20 Br F3'
_chemical_formula_weight         385.26
_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
_audit_creation_date             2015-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 131.354(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5693(7)
_cell_length_b                   10.6960(4)
_cell_length_c                   19.7220(12)
_cell_measurement_reflns_used    3566
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.9570
_cell_measurement_theta_min      4.7580
_cell_volume                     1673.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -50.00   25.00   1.0000    1.1450
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000   60.0000 75

  2 omega   87.00  124.00   1.0000    1.1450
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000   30.0000 37

  3 omega   38.00  158.00   1.0000    4.5750
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000    0.0000 120

  4 omega   77.00  120.00   1.0000    4.5750
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -120.0000 43

  5 omega   73.00  105.00   1.0000    4.5750
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   30.0000 32

  6 omega   48.00   95.00   1.0000    4.5750
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 47

  7 omega   39.00  119.00   1.0000    4.5750
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   30.0000 80

  8 omega   40.00   91.00   1.0000    4.5750
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 51

  9 omega   36.00   80.00   1.0000    4.5750
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 44

 10 omega   35.00  102.00   1.0000    4.5750
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   90.0000 67

 11 omega   33.00   73.00   1.0000    4.5750
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -180.0000 40

 12 omega -116.00  -54.00   1.0000    1.1450
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -38.0000   90.0000 62

 13 omega -113.00  -36.00   1.0000    1.1450
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  178.0000   90.0000 77

 14 omega  -37.00   13.00   1.0000    1.1450
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000  120.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0137649000
_diffrn_orient_matrix_UB_12      0.0398900000
_diffrn_orient_matrix_UB_13      -0.0797724000
_diffrn_orient_matrix_UB_21      -0.0077399000
_diffrn_orient_matrix_UB_22      0.1381680000
_diffrn_orient_matrix_UB_23      0.0190400000
_diffrn_orient_matrix_UB_31      0.1934727000
_diffrn_orient_matrix_UB_32      0.0085022000
_diffrn_orient_matrix_UB_33      0.0641731000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7739
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         4.770
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.529
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.2673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2693
_reflns_number_total             3166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00419_si_001.cif
_cod_data_source_block           103-129-2915_amp5
_cod_database_code               4036762
_chemical_oxdiff_formula         'C19 H20 Br F3'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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. Uiso/Uaniso restraints and constraints
Uanis(C1A) = Uanis(Br1A)
Uanis(Br1) = Uanis(C1)
3. Others
 Sof(Br1A)=Sof(F1A)=Sof(C1A)=Sof(F2A)=Sof(H2B)=Sof(F3A)=1-FVAR(1)
 Sof(Br1)=Sof(F1)=Sof(C1)=Sof(F2)=Sof(H2A)=Sof(F3)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2(H2A), C2(H2B), C3(H3)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C14(H14), C15(H15), C17(H17)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_shelx_res_checksum              47037
_shelx_hkl_checksum              51279
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'