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_7154579
_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         'C26 H25 F3'
_chemical_formula_sum            'C26 H25 F3'
_chemical_formula_weight         394.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-02-04
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2015-02-04 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                76.862(4)
_cell_angle_beta                 87.228(3)
_cell_angle_gamma                75.716(4)
_cell_formula_units_Z            2
_cell_length_a                   9.1770(4)
_cell_length_b                   10.3545(6)
_cell_length_c                   11.2833(5)
_cell_measurement_reflns_used    3904
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8299
_cell_measurement_theta_min      2.6908
_cell_volume                     1011.80(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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 16.2096
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_details
;
  1 omega  -55.00   49.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223   19.0000  -90.0000 104

  2 omega  -93.00   -3.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  -57.0000   90.0000 90

  3 omega  -34.00   44.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223   57.0000  -30.0000 78

  4 omega  -87.00  -43.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  178.0000  -60.0000 44

  5 omega   41.00   67.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000  -60.0000 26

  6 omega   -9.00   33.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   89.0000   64.0000 42

  7 omega   19.00   66.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000 -120.0000 47

  8 omega -100.00  -58.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  178.0000   30.0000 42

  9 omega  -76.00  -51.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  -77.0000  -60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0323350000
_diffrn_orient_matrix_UB_12      0.0336814000
_diffrn_orient_matrix_UB_13      -0.0580890000
_diffrn_orient_matrix_UB_21      -0.0157972000
_diffrn_orient_matrix_UB_22      -0.0616128000
_diffrn_orient_matrix_UB_23      -0.0068445000
_diffrn_orient_matrix_UB_31      -0.0711794000
_diffrn_orient_matrix_UB_32      0.0180629000
_diffrn_orient_matrix_UB_33      0.0273159000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10027
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.70
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tables
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0435P)^2^+0.5170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                3788
_reflns_number_total             4642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01072a2.cif
_cod_data_source_block           avv9
_cod_depositor_comments
'Adding full bibliography for 7154577--7154582.cif.'
_cod_original_cell_volume        1011.79(8)
_cod_database_code               7154579
_chemical_oxdiff_formula         'c26 h25 f3'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51