Cyclization Cascades via N-Amidyl Radicals toward Highly Functionalized Heterocyclic Scaffolds.
Fuentes, Noelia; Kong, Wangqing; Fernández-Sánchez, Luis; Merino, Estíbaliz; Nevado, Cristina; Journal of the American Chemical Society 137 (2015) 964–973; doi:10.1021/ja5115858

data_4123315
_publ_section_title
;
 Cyclization Cascades via N-Amidyl Radicals toward Highly Functionalized
 Heterocyclic Scaffolds.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              964
_journal_page_last               973
_journal_paper_doi               10.1021/ja5115858
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C27 H24 F3 N O'
_chemical_formula_sum            'C27 H24 F3 N O'
_chemical_formula_weight         435.47
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Olex2 1.2
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CrysAlisPro, version 1.171.37.31d (Agilent Technologies, 2012)
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CrysAlisPro, version 1.171.37.31d (Agilent Technologies, 2012)
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CrysAlisPro, version 1.171.36.20 (Agilent Technologies, 2012)
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<i>Mercury</i> (Macrae et al., 2006)
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Olex2 (Dolomanov et al., 2009), <i>PLATON for Windows</i> (Spek, 2003) and
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SHELXS97 (Sheldrick, 2008)
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;
  1 omega  -49.00   35.00   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615   37.0000   90.0000 70

  2 omega -130.00   48.80   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega   23.00   98.60   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615 -125.0000   60.0000 63

  4 omega   23.00   98.60   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615 -125.0000 -150.0000 63

  5 omega    1.00   82.60   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615  -99.0000  -90.0000 68

  6 omega   23.00   98.60   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615 -125.0000    0.0000 63

  7 omega    2.00   28.40   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615   91.0000  154.7511 22

  8 omega   35.00  115.40   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000    0.0000 67

  9 omega   82.00  178.00   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 80

 10 omega   38.00   98.00   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 50

 11 omega   34.00  145.60   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 93

 12 omega   35.00  115.40   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  150.0000 67

 13 omega  100.00  178.00   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000 -150.0000 65

 14 omega   38.00   98.00   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 50

 15 omega   35.00   90.20   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 46

 16 omega   82.00  178.00   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  150.0000 80

 17 omega  100.00  178.00   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000  150.0000 65

 18 omega   35.00  115.40   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -60.0000 67

 19 omega   38.00   98.00   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 50

 20 omega   57.00  148.20   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  120.0000 76

 21 omega   35.00  115.40   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -120.0000 67

 22 omega   82.00  178.00   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 80

 23 omega   35.00  115.40   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 67

 24 omega   35.00  115.40   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   90.0000 67

 25 omega   82.00  178.00   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -60.0000 80

 26 omega   39.00  142.20   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  120.0000 86

 27 omega -119.00   -7.40   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615  -77.0000  150.0000 93

 28 omega -119.00   -7.40   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615  -77.0000  -90.0000 93

 29 omega -115.00  -11.80   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7615  -57.0000 -180.0000 86

 30 omega    7.00  118.60   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615   77.0000   90.0000 93

 31 omega   11.00  114.20   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615   57.0000   30.0000 86

 32 omega    7.00  118.60   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7615   77.0000   60.0000 93

 33 omega   52.00  155.20   1.2000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   60.0000 86
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
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_diffrn_radiation_monochromator  mirror
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_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 1.000
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
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_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
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_refine_ls_goodness_of_fit_ref   1.041
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'w=1/[\s^2^(Fo^2^)+(0.0860P)^2^+0.9347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5115858_si_002.cif
_cod_data_source_block           nv1423
_cod_depositor_comments
'Adding full bibliography for 4123315--4123319.cif.'
_cod_database_code               4123315
_shelxl_version_number           2013-4
_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. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3: within 3A with sigma of 0.005 and sigma for terminal
atoms of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C24(H24), C25(H25), C26(H26), C27(H27), N1(H1)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              23216
_shelx_hkl_checksum              33712