Direct β-Alkylation of Ketones and Aldehydes via Pd-Catalyzed Redox Cascade.
Wang, Chengpeng; Dong, Guangbin; Journal of the American Chemical Society 140 (2018) 6057–6061; doi:10.1021/jacs.8b03530

data_4132377
_publ_section_title
;
 Direct \b-Alkylation of Ketones and Aldehydes via Pd-Catalyzed Redox
 Cascade.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6057
_journal_page_last               6061
_journal_paper_doi               10.1021/jacs.8b03530
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C26 H30 Fe O2'
_chemical_formula_sum            'C26 H30 Fe O2'
_chemical_formula_weight         430.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                93.601(2)
_cell_angle_beta                 102.190(2)
_cell_angle_gamma                111.741(2)
_cell_formula_units_Z            6
_cell_length_a                   13.6378(8)
_cell_length_b                   13.6481(8)
_cell_length_c                   19.0182(11)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.41
_cell_volume                     3174.9(3)
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/1 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            108888
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.573
_diffrn_reflns_theta_min         2.106
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1209 before and 0.0505 after correction.
The Ratio of minimum to maximum transmission is 0.9277.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       prism
_exptl_crystal_F_000             1368
_exptl_crystal_recrystallization_method
'obtained by slow evaporation of pentane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     793
_refine_ls_number_reflns         14670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+2.3213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11374
_reflns_number_total             14670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b03530_si_003.cif
_cod_data_source_block           wcp-4-150
_cod_database_code               4132377
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.930
_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:
 C13(H13), C13B(H13B), C14C(H14C), C13C(H13C), C14B(H14B), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C12B(H12C,H12D), C12(H12A,H12B), C12C(H12E,H12F), C15B(H15C,H15D), C16(H16A,
 H16B), C16B(H16C,H16D), C16C(H16E,H16F), C15C(H15E,H15F), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C5B(H5B), C9B(H9B), C4B(H4B), C5C(H5C), C3B(H3B), C5(H5), C2C(H2C), C8B(H8B),
 C2B(H2B), C3C(H3C), C3(H3), C2(H2), C21B(H21B), C10B(H10B), C21C(H21C),
 C10(H10), C20B(H20B), C4C(H4C), C4(H4), C18B(H18B), C7B(H7B), C6(H6),
 C19B(H19B), C19(H19), C7C(H7C), C8(H8), C19C(H19C), C18(H18), C6B(H6B),
 C20C(H20C), C9(H9), C9C(H9C), C6C(H6C), C7(H7), C21(H21), C8C(H8C), C18C(H18C),
  C20(H20), C10C(H10C)
2.d Idealised Me refined as rotating group:
 C25B(H25D,H25E,H25F), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C24B(H24D,
 H24E,H24F), C26B(H26D,H26E,H26F), C26C(H26G,H26H,H26I), C25C(H25G,H25H,H25I),
 C25(H25A,H25B,H25C), C24C(H24G,H24H,H24I)
;
_shelx_res_checksum              46471
_shelx_hkl_checksum              28089
_olex2_exptl_crystal_mounting_method 'mounted with a 20um-loop base'
_olex2_submission_special_instructions 'No special instructions were received'