Reactions of CF3-enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor ligands.
Iakovenko, Roman O.; Kazakova, Anna N.; Muzalevskiy, Vasiliy M.; Ivanov, Alexander Yu; Boyarskaya, Irina A.; Chicca, Andrea; Petrucci, Vanessa; Gertsch, Jürg; Krasavin, Mikhail; Starova, Galina L.; Zolotarev, Andrey A.; Avdontceva, Margarita S.; Nenajdenko, Valentine G.; Vasilyev, Aleksander V.; Organic & biomolecular chemistry 13 (2015) 8827–8842; doi:10.1039/c5ob01072a

data_7154582
_publ_section_title
;
 Reactions of CF3-enones with arenes under superelectrophilic activation:
 a pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor
 ligands.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8827
_journal_page_last               8842
_journal_paper_doi               10.1039/c5ob01072a
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C19 H21 F3 O Si'
_chemical_formula_sum            'C19 H21 F3 O Si'
_chemical_formula_weight         350.45
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-02-10
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2015-02-10 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.274(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1449(3)
_cell_length_b                   7.95800(16)
_cell_length_c                   16.5726(4)
_cell_measurement_reflns_used    10582
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0520
_cell_measurement_theta_min      5.4270
_cell_volume                     1841.11(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
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9947
_diffrn_measurement_details
;
  1 omega  -49.00  -23.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000 -150.0000 26

  2 omega  -86.00  -36.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -178.0000  120.0000 50

  3 omega  -49.00   36.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -30.0000 85

  4 omega  -39.00  -11.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   30.0000 28

  5 omega -119.00  -54.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000 -150.0000 65

  6 omega -113.00  -88.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   30.0000 25

  7 omega  -77.00   33.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   86.0000   40.0000 110

  8 omega   91.00  117.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   30.0000 26

  9 omega   60.00  129.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -90.0000 69

 10 omega   57.00   83.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 26

 11 omega  135.00  164.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000    0.0000 29

 12 omega   84.00  109.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 25

 13 omega   35.00   71.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 36

 14 omega   40.00   97.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 57

 15 omega  102.00  147.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 45

 16 omega   38.00   77.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 39

 17 omega  100.00  139.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -30.0000 39

 18 omega   57.00   83.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -30.0000 26

 19 omega   55.00  105.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 50

 20 omega   80.00  113.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 33

 21 omega  105.00  135.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 30

 22 omega   85.00  173.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 88

 23 omega   90.00  115.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 25

 24 omega  152.00  177.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 25

 25 omega   86.00  112.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 26

 26 omega   54.00   86.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 32

 27 omega   48.00  103.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 55

 28 omega  107.00  133.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -150.0000 26

 29 omega   38.00   71.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 33

 30 omega   62.00   88.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 26

 31 omega  107.00  143.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  120.0000 36

 32 omega   44.00  110.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -90.0000 66

 33 omega   75.00  101.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 26

 34 omega   54.00  109.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 55

 35 omega   96.00  132.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 36

 36 omega   38.00   66.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 28

 37 omega  110.00  147.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 37

 38 omega   51.00   78.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 27

 39 omega   85.00  176.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 91

 40 omega   58.00   94.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -60.0000 36

 41 omega  101.00  126.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 25

 42 omega   59.00   95.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 36

 43 omega   30.00   61.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 31

 44 omega   73.00   98.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 25

 45 omega   54.00  108.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 54

 46 omega   90.00  115.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 25

 47 omega   52.00  109.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 57

 48 omega   63.00  103.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  120.0000 40

 49 omega  109.00  139.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 30

 50 omega  149.00  176.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 27

 51 omega   98.00  124.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 26

 52 omega  137.00  164.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 27

 53 omega   85.00  110.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 25

 54 omega   80.00  105.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -180.0000 25

 55 omega   46.00   94.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -25.0000 -172.8416 48
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0118156000
_diffrn_orient_matrix_UB_12      -0.1629024000
_diffrn_orient_matrix_UB_13      -0.0475638000
_diffrn_orient_matrix_UB_21      -0.0824485000
_diffrn_orient_matrix_UB_22      0.0545898000
_diffrn_orient_matrix_UB_23      -0.0672325000
_diffrn_orient_matrix_UB_31      0.0723366000
_diffrn_orient_matrix_UB_32      0.0892383000
_diffrn_orient_matrix_UB_33      -0.0457516000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22291
_diffrn_reflns_theta_full        72.50
_diffrn_reflns_theta_max         72.50
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84011
_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    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0519P)^2^+0.4654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                3321
_reflns_number_total             3651
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01072a2.cif
_cod_data_source_block           avv_23
_cod_depositor_comments
'Adding full bibliography for 7154577--7154582.cif.'
_cod_database_code               7154582
_chemical_oxdiff_formula         'c16 h14 O2 Si1 f6'
_reflns_odcompleteness_completeness 94.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95