Ligand-Enabled, Palladium-Catalyzed β-C(sp<sup>3</sup>)-H Arylation of Weinreb Amides.
Park, Hojoon; Chekshin, Nikita; Shen, Peng-Xiang; Yu, Jin-Quan; ACS catalysis 8 (2018) 9292–9297; doi:10.1021/acscatal.8b03014

data_4515515
_publ_section_title
;
 Ligand-Enabled, Palladium-Catalyzed \b-C(sp<sup>3</sup>)-H Arylation of
 Weinreb Amides.
;
_journal_issue                   10
_journal_name_full               'ACS catalysis'
_journal_page_first              9292
_journal_page_last               9297
_journal_paper_doi               10.1021/acscatal.8b03014
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C21 H22 F N O4'
_chemical_formula_sum            'C21 H22 F N O4'
_chemical_formula_weight         371.39
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-04
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.954(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.4465(18)
_cell_length_b                   6.4873(4)
_cell_length_c                   22.0138(15)
_cell_measurement_reflns_used    9110
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.343
_cell_measurement_theta_min      3.498
_cell_volume                     3609.3(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Platinum135 CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Platinum135'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            54256
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.379
_diffrn_reflns_theta_min         1.748
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  0.3129
_exptl_absorpt_correction_T_min  0.2122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1564 before and 0.0833 after correction. The Ratio of minimum to maximum transmission is 0.6782. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       Block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         6618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0534P)^2^+1.0939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5973
_reflns_number_total             6618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03014_si_001.cif
_cod_data_source_block           Yu103
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4515515
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.902
_shelx_estimated_absorpt_t_min   0.837
_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:
 C4(H4), C4'(H4')
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B), C3'(H3'A,H3'B), C12'(H12C,H12D)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C14(H14), C15(H15), C17(H17), C18(H18),
 C6'(H6'), C7'(H7'), C9'(H9'), C10'(H10'), C14'(H14'), C15'(H15'), C17'(H17'),
 C18'(H18')
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C19'(H19D,H19E,
 H19F), C20'(H20D,H20E,H20F), C21'(H21D,H21E,H21F)
;
_shelx_res_checksum              63780
_shelx_hkl_checksum              78320
_olex2_submission_special_instructions 'No special instructions were received'