Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides.
Derosa, Joseph; Kleinmans, Roman; Tran, Van T.; Karunananda, Malkanthi K.; Wisniewski, Steven R.; Eastgate, Martin D.; Engle, Keary M.; Journal of the American Chemical Society 140 (2018) 17878–17883; doi:10.1021/jacs.8b11942

data_4133633
_publ_section_title
;
 Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides.
;
_journal_issue                   51
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17878
_journal_page_last               17883
_journal_paper_doi               10.1021/jacs.8b11942
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C26 H29 N O4'
_chemical_formula_sum            'C26 H29 N O4'
_chemical_formula_weight         419.50
_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     direct
_audit_creation_date             2018-05-18
_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                 97.482(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.4479(6)
_cell_length_b                   15.9921(11)
_cell_length_c                   30.118(2)
_cell_measurement_reflns_used    6156
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.906
_cell_measurement_theta_min      2.958
_cell_volume                     4511.8(5)
_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 APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\f and \w 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  0.0983
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            49098
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.495
_diffrn_reflns_theta_min         2.960
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker Microstar FR-592'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1070 before and 0.0685 after correction. The Ratio of minimum to maximum transmission is 0.8983. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       needle
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         8289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0711
_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^)+(0.0632P)^2^+4.1906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1761
_refine_ls_wR_factor_ref         0.1947
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5701
_reflns_number_total             8289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b11942_si_002.cif
_cod_data_source_block           engle124_0m_a
_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/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/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               4133633
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.846
_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.a Ternary CH refined with riding coordinates:
 C8(H8), C8'(H8')
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C16(H16A,H16B), C18(H18A,H18B), C7'(H7'A,H7'B), C16'(H16C,H16D),
 C18'(H18C,H18D)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13),
  C14(H14), C20(H20), C21(H21), C23(H23), N1'(H1'), C1'(H1'A), C2'(H2'),
 C3'(H3'), C4'(H4'), C5'(H5'), C10'(H10'), C11'(H11'), C13'(H13'), C14'(H14'),
 C20'(H20'), C21'(H21'), C23'(H23')
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C15'(H15D,H15E,
 H15F), C25'(H25D,H25E,H25F), C26'(H26D,H26E,H26F)
;
_shelx_res_checksum              70458
_shelx_hkl_checksum              48121
_olex2_submission_special_instructions 'No special instructions were received'