Nickel-catalysed radical tandem cyclisation/arylation: practical synthesis of 4-benzyl-3,3-difluoro-γ-lactams.
Mai, Wen-Peng; Wang, Fei; Zhang, Xiao-Feng; Wang, Shi-Min; Duan, Qun-Peng; Lu, Kui; Organic & biomolecular chemistry 16 (2018) 6491–6498; doi:10.1039/c8ob01389f

data_7156383
_publ_section_title
;
 Nickel-catalysed radical tandem cyclisation/arylation: practical
 synthesis of 4-benzyl-3,3-difluoro-\g-lactams.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6491
_journal_page_last               6498
_journal_paper_doi               10.1039/c8ob01389f
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C19 H15 F2 N O2'
_chemical_formula_sum            'C19 H15 F2 N O2'
_chemical_formula_weight         327.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-26
_audit_creation_method
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
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_audit_update_record
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2018-01-26 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                75.270(17)
_cell_angle_beta                 68.659(18)
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_cell_formula_units_Z            2
_cell_length_a                   9.5617(18)
_cell_length_b                   9.7384(18)
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_cell_measurement_temperature    293(2)
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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omega____ theta____ kappa____ phi______ frames
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  2 omega -102.00  -15.00   1.0000    1.0000
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  3 omega  -34.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega  -34.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega   -4.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega  -35.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega    9.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   24.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   11.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega    2.00   73.00   1.0000    1.0000
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 11 omega   38.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 12 omega   71.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 65

 13 omega  127.00  166.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 39

 14 omega   94.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 28

 15 omega   39.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 28

 16 omega   39.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   90.0000 59

 17 omega  108.00  134.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 26

 18 omega   44.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   37.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 37

 20 omega  140.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 21 omega   37.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 74

 22 omega   38.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 23 omega   42.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 30

 24 omega   79.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 28

 25 omega   38.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 32

 26 omega   37.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 25

 27 omega  103.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 26

 28 omega   82.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 27

 29 omega   40.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 36

 30 omega  135.00  161.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 26

 31 omega  103.00  153.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   90.0000 50

 32 omega   59.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 26

 33 omega   53.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
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_refine_ls_R_factor_all          0.0719
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0968P)^2^+0.0916P] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01389f2.cif
_cod_data_source_block           20180137
_cod_depositor_comments          'Adding full bibliography for 7156383.cif.'
_cod_original_cell_volume        775.2(3)
_cod_database_code               7156383
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H30O5F2
_shelx_estimated_absorpt_t_max   0.884
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_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_olex2_submission_special_instructions 'No special instructions were received'