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_7154580
_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         'C22 H16 Cl F3'
_chemical_formula_sum            'C22 H16 Cl F3'
_chemical_formula_weight         372.80
_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             2014-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-02-04 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.018(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5842(4)
_cell_length_b                   9.2772(3)
_cell_length_c                   17.8208(6)
_cell_measurement_reflns_used    3108
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.4450
_cell_measurement_theta_min      4.9630
_cell_volume                     1749.86(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    '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 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
  1 omega  -13.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1287   38.0000   60.0000 27

  2 omega  -50.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1287   38.0000  -30.0000 79

  3 omega  -47.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1287   38.0000   60.0000 32

  4 omega   60.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1287  178.0000 -180.0000 42

  5 omega   55.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1287 -178.0000  -90.0000 49

  6 omega  140.00  166.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 26

  7 omega   38.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 52

  8 omega   49.00   94.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 45

  9 omega   43.00   78.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 35

 10 omega  118.00  143.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 25

 11 omega   49.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 46

 12 omega   95.00  121.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   90.0000 26

 13 omega   37.00   78.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 41

 14 omega  131.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 39

 15 omega  117.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  -30.0000 56

 16 omega   30.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  -30.0000 61

 17 omega   83.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1287  178.0000   60.0000 47

 18 omega   98.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1287  178.0000 -120.0000 32

 19 omega   84.00  142.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 58

 20 omega   70.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 25

 21 omega   49.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  120.0000 26

 22 omega  127.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 48

 23 omega   88.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 35

 24 omega   37.00   66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 29

 25 omega   62.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 25

 26 omega  102.00  127.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 25

 27 omega   94.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 12
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0858542000
_diffrn_orient_matrix_UB_12      0.0106543000
_diffrn_orient_matrix_UB_13      0.0696091000
_diffrn_orient_matrix_UB_21      0.0639288000
_diffrn_orient_matrix_UB_22      0.1347522000
_diffrn_orient_matrix_UB_23      -0.0333606000
_diffrn_orient_matrix_UB_31      -0.0986156000
_diffrn_orient_matrix_UB_32      0.0964792000
_diffrn_orient_matrix_UB_33      0.0389169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7629
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         4.18
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59546
_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    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.054
_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     235
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0531P)^2^+0.5078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0983
_reflns_number_gt                2592
_reflns_number_total             3031
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01072a2.cif
_cod_data_source_block           122
_cod_depositor_comments
'Adding full bibliography for 7154577--7154582.cif.'
_cod_original_cell_volume        1749.87(10)
_cod_database_code               7154580
_chemical_oxdiff_formula         'C10 h10 F3 P Cl'
_reflns_odcompleteness_completeness 88.94
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C3(H3), C6(H6), C16(H16), C22(H22), C2(H2), C15(H15), C23(H23),
 C18(H18), C24(H24), C26(H26), C25(H25), C1(H1)
;