Rac-(6S)-6-Hydroxy-6-{2-[2-(propan-2-ylidene)hydrazinylidene]propyl} indolo[2,1-b]quinazolin-12(6H)-one

Matthew E. Rodstein; Paul D. Steffen; Bogdana Krivogorsky; Peter Grundt

doi:10.1107/S1600536811037408

Rac-(6S)-6-Hydroxy-6-{2-[2-(propan-2-ylidene)hydrazinylidene]propyl} indolo[2,1-b]quinazolin-12(6H)-one

Matthew E. Rodstein
, Paul D. Steffen
, Bogdana Krivogorsky
, Peter Grundt

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

Thechiraltitlecompound,C ₂₁H ₂₀N ₄O ₂, crystallizes as a racemic mixture. In the crystal, molecules form centrosymmetric π-overlapping dimers [inter-planar distance = 3.338 (6) Å], which are further connected along the a axis forming centrosymmetric dimers via O-H⋯N hydrogen bonds. C-H⋯O interactions are also observed. The indolo[2,1-b]quinazoline group is somewhat bent, with a small dihedral angle of 6.3 (4)° between the plane of the quinazoline system and the plane of the benzene ring of the indole moiety. The C=N-N=C atoms of the azine group is oriented almost perpendicular [84.1 (2)°] to the mean plane of the quinazoline system.

Original language	English (US)
Pages (from-to)	o2695-o2696
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	67
Issue number	10
DOIs	https://doi.org/10.1107/S1600536811037408
State	Published - Oct 2011

Keywords

R factor = 0.062
T = 100 K
mean σ(C-C) = 0.006 Å
single-crystal X-ray study
wR factor = 0.161; data-to-parameter ratio = 11.9

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@article{251e3bdce49b4b28b899b46fc4469a81,

title = "Rac-(6S)-6-Hydroxy-6-\{2-[2-(propan-2-ylidene)hydrazinylidene]propyl\} indolo[2,1-b]quinazolin-12(6H)-one",

abstract = "Thechiraltitlecompound,C 21H 20N 4O 2, crystallizes as a racemic mixture. In the crystal, molecules form centrosymmetric π-overlapping dimers [inter-planar distance = 3.338 (6) {\AA}], which are further connected along the a axis forming centrosymmetric dimers via O-H⋯N hydrogen bonds. C-H⋯O interactions are also observed. The indolo[2,1-b]quinazoline group is somewhat bent, with a small dihedral angle of 6.3 (4)° between the plane of the quinazoline system and the plane of the benzene ring of the indole moiety. The C=N-N=C atoms of the azine group is oriented almost perpendicular [84.1 (2)°] to the mean plane of the quinazoline system.",

keywords = "R factor = 0.062, T = 100 K, mean σ(C-C) = 0.006 {\AA}, single-crystal X-ray study, wR factor = 0.161; data-to-parameter ratio = 11.9",

author = "Rodstein, \{Matthew E.\} and Steffen, \{Paul D.\} and Bogdana Krivogorsky and Peter Grundt",

year = "2011",

month = oct,

doi = "10.1107/S1600536811037408",

language = "English (US)",

volume = "67",

pages = "o2695--o2696",

journal = "Acta Crystallographica Section E: Structure Reports Online",

issn = "1600-5368",

publisher = "International Union of Crystallography",

number = "10",

}

TY - JOUR

T1 - Rac-(6S)-6-Hydroxy-6-{2-[2-(propan-2-ylidene)hydrazinylidene]propyl} indolo[2,1-b]quinazolin-12(6H)-one

AU - Rodstein, Matthew E.

AU - Steffen, Paul D.

AU - Krivogorsky, Bogdana

AU - Grundt, Peter

PY - 2011/10

Y1 - 2011/10

N2 - Thechiraltitlecompound,C 21H 20N 4O 2, crystallizes as a racemic mixture. In the crystal, molecules form centrosymmetric π-overlapping dimers [inter-planar distance = 3.338 (6) Å], which are further connected along the a axis forming centrosymmetric dimers via O-H⋯N hydrogen bonds. C-H⋯O interactions are also observed. The indolo[2,1-b]quinazoline group is somewhat bent, with a small dihedral angle of 6.3 (4)° between the plane of the quinazoline system and the plane of the benzene ring of the indole moiety. The C=N-N=C atoms of the azine group is oriented almost perpendicular [84.1 (2)°] to the mean plane of the quinazoline system.

AB - Thechiraltitlecompound,C 21H 20N 4O 2, crystallizes as a racemic mixture. In the crystal, molecules form centrosymmetric π-overlapping dimers [inter-planar distance = 3.338 (6) Å], which are further connected along the a axis forming centrosymmetric dimers via O-H⋯N hydrogen bonds. C-H⋯O interactions are also observed. The indolo[2,1-b]quinazoline group is somewhat bent, with a small dihedral angle of 6.3 (4)° between the plane of the quinazoline system and the plane of the benzene ring of the indole moiety. The C=N-N=C atoms of the azine group is oriented almost perpendicular [84.1 (2)°] to the mean plane of the quinazoline system.

KW - R factor = 0.062

KW - T = 100 K

KW - mean σ(C-C) = 0.006 Å

KW - single-crystal X-ray study

KW - wR factor = 0.161; data-to-parameter ratio = 11.9

UR - https://www.scopus.com/pages/publications/80054983934

UR - https://www.scopus.com/pages/publications/80054983934#tab=citedBy

U2 - 10.1107/S1600536811037408

DO - 10.1107/S1600536811037408

M3 - Article

C2 - 22065467

AN - SCOPUS:80054983934

SN - 1600-5368

VL - 67

SP - o2695-o2696

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 10

ER -

Rac-(6S)-6-Hydroxy-6-{2-[2-(propan-2-ylidene)hydrazinylidene]propyl} indolo[2,1-b]quinazolin-12(6H)-one

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