Synthesis of Dihydropyridinone-Fused Indoles and α-Carbolines via N-Heterocyclic Carbene-Catalyzed [3 + 3] Annulation of Indolin-2-imines and Bromoenals.
Yi, Liang; Zhang, Yuyang; Zhang, Zhao-Fei; Sun, Dequn; Ye, Song; Organic letters 19 (2017) 2286–2289; doi:10.1021/acs.orglett.7b00820

data_1545780
_publ_section_title
;
 Synthesis of Dihydropyridinone-Fused Indoles and \a-Carbolines via
 N-Heterocyclic Carbene-Catalyzed [3 + 3] Annulation of Indolin-2-imines
 and Bromoenals.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2286
_journal_page_last               2289
_journal_paper_doi               10.1021/acs.orglett.7b00820
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C25 H21 Br N2 O3 S'
_chemical_formula_sum            'C25 H21 Br N2 O3 S'
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_symmetry_space_group_name_Hall  '-P 2ybc'
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Olex2 1.2
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CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
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CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
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AFC10: Fixed Chi 2 circle
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Rigaku Saturn724+ (2x2 bin mode)
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_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1545780.cif.
;
_cod_database_code               1545780
_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. Restrained distances
 C25A-C20 = C25-C20 = C23-C22 = C21-C20 = C24-C23 = C22-C21 = C25-C24
 1.39 with sigma of 0.01
 S1-C13A = S1-C13
 1.76 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C21A \\sim C24A \\sim C22A
\\sim C25A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C18A
\\sim C13A \\sim C14A \\sim C19A \\sim C15A \\sim C16A \\sim C17A: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C24A) \\sim Ueq, Uanis(C25A) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C24) \\sim Ueq, Uanis(C21A) \\sim Ueq, Uanis(C22A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq,
Uanis(C13A) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(C15A) \\sim Ueq,
Uanis(C16A) \\sim Ueq, Uanis(C17A) \\sim Ueq, Uanis(C18A) \\sim Ueq,
Uanis(C19A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H23A)=Sof(C21A)=Sof(H21A)=Sof(C24A)=Sof(H24A)=Sof(C22A)=Sof(H22A)=
 Sof(C25A)=Sof(H25A)=1-FVAR(1)
 Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C25)=
 Sof(H25)=FVAR(1)
 Sof(C18A)=Sof(H18A)=Sof(C13A)=Sof(C14A)=Sof(H14A)=Sof(C19A)=Sof(H19D)=
 Sof(H19E)=Sof(H19F)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=1-FVAR(2)
 Sof(C13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(C17)=Sof(H17)=
 Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18), C21(H21),
 C22(H22), C23(H23), C23(H23A), C24(H24), C25(H25), C21A(H21A), C18A(H18A),
 C24A(H24A), C14A(H14A), C15A(H15A), C22A(H22A), C17A(H17A), C25A(H25A)
5.d Idealised Me refined as rotating group:
 C9(H0AA,H0AB,H0AC), C19(H19A,H19B,H19C), C19A(H19D,H19E,H19F)
;
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