Transition-Metal-Free α-Arylation of Nitroketones with Diaryliodonium Salts for the Synthesis of Tertiary α-Aryl, α-Nitro Ketones
An, Yang; Zhang, Xiao-Ming; Li, Ze-Yu; Xiong, Wen-Hui; Yu, Run-Dong; Zhang, Fu-Min; Chemical Communications  (2018) –; doi:10.1039/C8CC08920E

data_7122661
_publ_section_title
;
 Transition-Metal-Free \a-Arylation of Nitroketones with Diaryliodonium
 Salts for the Synthesis of Tertiary \a-Aryl, \a-Nitro Ketones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08920E
_journal_year                    2018
_chemical_formula_moiety         'C12 H17 N O S'
_chemical_formula_sum            'C12 H17 N O S'
_chemical_formula_weight         223.33
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-07-31 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.226(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7338(6)
_cell_length_b                   10.3698(8)
_cell_length_c                   13.3729(9)
_cell_measurement_reflns_used    1076
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.2090
_cell_measurement_theta_min      3.6150
_cell_volume                     1211.14(15)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega  -89.00  -64.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2711  178.0000  -30.0000 25

  2 omega  -16.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -99.0000  -30.0000 81

  3 omega    4.00   44.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -99.0000 -150.0000 40

  4 omega  -18.00    8.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000 -150.0000 26

  5 omega  -39.00   40.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000 -150.0000 79
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0118427000
_diffrn_orient_matrix_UB_12      0.0610737000
_diffrn_orient_matrix_UB_13      -0.0228050000
_diffrn_orient_matrix_UB_21      -0.0495139000
_diffrn_orient_matrix_UB_22      -0.0181471000
_diffrn_orient_matrix_UB_23      -0.0396795000
_diffrn_orient_matrix_UB_31      -0.0631230000
_diffrn_orient_matrix_UB_32      0.0253551000
_diffrn_orient_matrix_UB_33      0.0267000000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4799
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.40
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73545
_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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.042
_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     140
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0609
_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^)+(0.0751P)^2^+0.1276P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1837
_reflns_number_gt                1337
_reflns_number_total             2347
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc08920e2.cif
_cod_data_source_block           anyang_0508
_cod_original_cell_volume        1211.15(15)
_cod_database_code               7122661
_reflns_odcompleteness_completeness 97.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{S1', C8}
{C8', S1}
3. Uiso/Uaniso restraints and constraints
Uanis(C8') = Uanis(S1)
Uanis(S1') = Uanis(C8)
4. Others
 Fixed Sof: H9A(0.15) H9B(0.85) H10(0.15) H10A(0.85) S1'(0.2) C8'(0.2)
 H8'(0.2) S1(0.8) C8(0.8) H8(0.8)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C11(H11A,H11B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9A), C9(H9B), C10(H10), C10(H10A), C8'(H8'), C8(H8)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_date_sample_data_collection 2018-05-08
_olex2_submission_special_instructions 'No special instructions were received'