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_4133632
_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         'C21 H27 N O2'
_chemical_formula_sum            'C21 H27 N O2'
_chemical_formula_weight         325.43
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-09-24
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Olex2 1.2-beta 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
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_cell_angle_gamma                90
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_cell_length_c                   23.934(4)
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_computing_cell_refinement       'SAINT v8.37A (Bruker, 2016)'
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_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_diffrn_detector                 'Bruker APEX-II CCD'
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_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
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_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
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_diffrn_source                   'Micro Focus Rotating Anode'
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_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1187 before and 0.0528 after correction. The '
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       plank
_exptl_crystal_F_000             704
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_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         3375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0378P)^2^+1.0741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2696
_reflns_number_total             3375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b11942_si_004.cif
_cod_data_source_block           engle149
_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_original_cell_volume        1837.2(5)
_cod_database_code               4133632
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.984
_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: 
 C3(H3) 
2.b Secondary CH2 refined with riding coordinates: 
 C2(H2A,H2B), C4(H4A,H4B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), 
 C17(H17) 
2.d Idealised Me refined as rotating group: 
 C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B, 
 H21C) 
;
_shelx_res_checksum              9385
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_olex2_submission_special_instructions 'No special instructions were received'