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_7154578
_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 H24 Cl F3'
_chemical_formula_sum            'C26 H24 Cl F3'
_chemical_formula_weight         428.90
_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
_audit_creation_date             2015-01-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2015-02-04 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                73.153(4)
_cell_angle_beta                 87.926(4)
_cell_angle_gamma                76.728(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3350(4)
_cell_length_b                   10.6357(5)
_cell_length_c                   11.4303(5)
_cell_measurement_reflns_used    4834
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.8340
_cell_measurement_theta_min      4.0370
_cell_volume                     1056.57(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)
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_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
  1 omega  -87.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000 -120.0000 120

  2 omega  -18.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 45

  3 omega  -17.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -90.0000 40

  4 omega   75.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  -60.0000 38

  5 omega   57.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   60.0000 61

  6 omega    1.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000   60.0000 81

  7 omega   62.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 25

  8 omega  145.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -180.0000 32

  9 omega  129.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   60.0000 48

 10 omega  115.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   60.0000 41

 11 omega  101.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 45

 12 omega   48.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 43

 13 omega   48.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 53

 14 omega  121.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 26

 15 omega   81.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 33

 16 omega   62.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 36

 17 omega   29.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 48

 18 omega   68.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   30.0000 26

 19 omega   92.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -120.0000 44

 20 omega   56.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 59

 21 omega  101.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 51

 22 omega   90.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  150.0000 87

 23 omega   42.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 71

 24 omega   55.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 41

 25 omega   38.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 25

 26 omega   74.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 48

 27 omega  116.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 56
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1225865000
_diffrn_orient_matrix_UB_12      -0.0788645000
_diffrn_orient_matrix_UB_13      0.0268109000
_diffrn_orient_matrix_UB_21      0.1021645000
_diffrn_orient_matrix_UB_22      -0.1151620000
_diffrn_orient_matrix_UB_23      0.0959492000
_diffrn_orient_matrix_UB_31      -0.0575828000
_diffrn_orient_matrix_UB_32      0.0684922000
_diffrn_orient_matrix_UB_33      0.0996332000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7883
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         4.043
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80446
_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_density_diffrn    1.348
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.5885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3587
_reflns_number_total             3906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01072a2.cif
_cod_data_source_block           avv_24
_cod_depositor_comments
'Adding full bibliography for 7154577--7154582.cif.'
_cod_original_cell_volume        1056.58(9)
_cod_database_code               7154578
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C26 H24 F3 Cl'
_reflns_odcompleteness_completeness 91.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C17(H17), C15(H15), C23(H23), C27(H27), C6(H6), C8(H8), C24(H24),
 C26(H26)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C21(H21A,H21B,H21C), C29(H29A,H29B,H29C), C20(H20A,H20B,
 H20C)
;
_shelx_res_checksum              59214
_olex2_submission_special_instructions 'No special instructions were received'