A Cu-mediated one-pot Michael addition/α-arylation strategy using a diaryliodonium salt: a direct and efficient approach to α-aryl-β-substituted cyclic ketone scaffolds.
Pan, Jin-Long; Chen, Tao; Zhang, Zhi-Qiang; Li, Yi-Fan; Zhang, Xiao-Ming; Zhang, Fu-Min; Chemical communications (Cambridge, England) 52 (2016) 2382–2385; doi:10.1039/c5cc09837h

data_7118341
_publ_section_title
;
 A Cu-mediated one-pot Michael addition/\a-arylation strategy using a
 diaryliodonium salt: a direct and efficient approach to
 \a-aryl-\b-substituted cyclic ketone scaffolds.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2382
_journal_page_last               2385
_journal_paper_doi               10.1039/c5cc09837h
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration none
_chemical_formula_moiety         'C16 H22 O'
_chemical_formula_sum            'C16 H22 O'
_chemical_formula_weight         230.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.26 svn.r2951 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2015-10-04 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.097(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6982(3)
_cell_length_b                   18.9135(10)
_cell_length_c                   13.0889(7)
_cell_measurement_reflns_used    1915
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5660
_cell_measurement_theta_min      4.6890
_cell_volume                     1405.05(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
  1 omega  -70.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000    0.0000 26

  2 omega   33.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   62.0000  -32.0000 26

  3 omega -109.00  -39.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  150.0000 70

  4 omega   76.00  102.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  150.0000 26

  5 omega   24.00   69.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  150.0000 45

  6 omega  -14.00   52.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  150.0000 66

  7 omega   51.00  125.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -60.0000 74

  8 omega   43.00   81.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  120.0000 38

  9 omega   40.00   89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -180.0000 49

 10 omega   67.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  120.0000 26

 11 omega   88.00  125.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000  -60.0000 37

 12 omega   70.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000   30.0000 101

 13 omega   41.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -30.0000 34

 14 omega   46.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000    0.0000 38

 15 omega   60.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   30.0000 33

 16 omega   38.00   63.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  120.0000 25

 17 omega  103.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   60.0000 75

 18 omega  148.00  174.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000  -60.0000 26

 19 omega   62.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  -90.0000 42

 20 omega   95.00  167.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000 -120.0000 72
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0409197000
_diffrn_orient_matrix_UB_12      -0.0109061000
_diffrn_orient_matrix_UB_13      -0.1137074000
_diffrn_orient_matrix_UB_21      0.1823744000
_diffrn_orient_matrix_UB_22      -0.0580372000
_diffrn_orient_matrix_UB_23      0.0308025000
_diffrn_orient_matrix_UB_31      -0.1965762000
_diffrn_orient_matrix_UB_32      -0.0561510000
_diffrn_orient_matrix_UB_33      -0.0096736000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5061
_diffrn_reflns_point_group_measured_fraction_full 0.669
_diffrn_reflns_point_group_measured_fraction_max 0.654
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.651
_diffrn_reflns_theta_min         4.119
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 617 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       0.0063(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3505
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0990P)^2^+0.0035P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.333
_reflns_Friedel_fraction_full    0.341
_reflns_Friedel_fraction_max     0.328
_reflns_number_gt                2953
_reflns_number_total             3505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc09837h4.cif
_cod_data_source_block           zhangfm0622
_cod_depositor_comments          'Adding full bibliography for 7118341.cif.'
_cod_original_cell_volume        1405.05(12)
_cod_database_code               7118341
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C21(H21), C22(H22), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C23(H23A,H23B), C24(H24A,
 H24B), C25(H25A,H25B), C1A(H1AA,H1AB), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B),
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              52022
_olex2_submission_special_instructions 'No special instructions were received'