2-Butyl-11-phenyl-5,10-dihydro-1H-benzo[e]imidazo[1,5-a][1,4]diazepine-1, 3(2H)-dione

Gary S. Nichol; Steven Gunawan; Justin Dietrich; Christopher Hulme

doi:10.1107/S1600536810005477

2-Butyl-11-phenyl-5,10-dihydro-1H-benzo[e]imidazo[1,5-a][1,4]diazepine-1, 3(2H)-dione

Gary S. Nichol, Steven Gunawan, Justin Dietrich, Christopher Hulme

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

2 Scopus citations

Abstract

The title compound, C₂₁H₂₁N₃O₂, was obtained following a five-step synthetic procedure yielding weakly diffracting rod and needle-shaped crystals which crystallized concomitantly. Structural analysis of a rod-shaped crystal showed that the central seven-membered heterocyclic ring adopts a conformation that is perhaps best described as a distorted boat, with the H-bearing (CH₂ and NH) atoms lying well out of the least-squares mean plane fitted through the other five atoms in the ring (r.m.s. deviation 0.075 Å). In the crystal, the compound packs as a twisted chain, which propagates along the b axis by means of an R ¹₂(6) motif formed by one of the carbonyl O atoms acting as a bifurcated acceptor in an N - H⋯O and C - H⋯O inter-action. No diffraction was observed from the needle-shaped crystals.

Original language	English (US)
Pages (from-to)	o625
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	66
Issue number	3
DOIs	https://doi.org/10.1107/S1600536810005477
State	Published - 2010

Keywords

Data-to-parameter ratio = 11.4
Mean σ(C-C) = 0.004 Å
R factor = 0.065
Single-crystal X-ray study
T = 100 K
WR factor = 0.181

ASJC Scopus subject areas

Chemistry(all)
Materials Science(all)
Condensed Matter Physics

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10.1107/S1600536810005477

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title = "2-Butyl-11-phenyl-5,10-dihydro-1H-benzo[e]imidazo[1,5-a][1,4]diazepine-1, 3(2H)-dione",

abstract = "The title compound, C21H21N3O2, was obtained following a five-step synthetic procedure yielding weakly diffracting rod and needle-shaped crystals which crystallized concomitantly. Structural analysis of a rod-shaped crystal showed that the central seven-membered heterocyclic ring adopts a conformation that is perhaps best described as a distorted boat, with the H-bearing (CH2 and NH) atoms lying well out of the least-squares mean plane fitted through the other five atoms in the ring (r.m.s. deviation 0.075 {\AA}). In the crystal, the compound packs as a twisted chain, which propagates along the b axis by means of an R 12(6) motif formed by one of the carbonyl O atoms acting as a bifurcated acceptor in an N - H⋯O and C - H⋯O inter-action. No diffraction was observed from the needle-shaped crystals.",

keywords = "Data-to-parameter ratio = 11.4, Mean σ(C-C) = 0.004 {\AA}, R factor = 0.065, Single-crystal X-ray study, T = 100 K, WR factor = 0.181",

author = "Nichol, {Gary S.} and Steven Gunawan and Justin Dietrich and Christopher Hulme",

year = "2010",

doi = "10.1107/S1600536810005477",

language = "English (US)",

volume = "66",

pages = "o625",

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

issn = "1600-5368",

publisher = "International Union of Crystallography",

number = "3",

}

TY - JOUR

T1 - 2-Butyl-11-phenyl-5,10-dihydro-1H-benzo[e]imidazo[1,5-a][1,4]diazepine-1, 3(2H)-dione

AU - Nichol, Gary S.

AU - Gunawan, Steven

AU - Dietrich, Justin

AU - Hulme, Christopher

PY - 2010

Y1 - 2010

N2 - The title compound, C21H21N3O2, was obtained following a five-step synthetic procedure yielding weakly diffracting rod and needle-shaped crystals which crystallized concomitantly. Structural analysis of a rod-shaped crystal showed that the central seven-membered heterocyclic ring adopts a conformation that is perhaps best described as a distorted boat, with the H-bearing (CH2 and NH) atoms lying well out of the least-squares mean plane fitted through the other five atoms in the ring (r.m.s. deviation 0.075 Å). In the crystal, the compound packs as a twisted chain, which propagates along the b axis by means of an R 12(6) motif formed by one of the carbonyl O atoms acting as a bifurcated acceptor in an N - H⋯O and C - H⋯O inter-action. No diffraction was observed from the needle-shaped crystals.

AB - The title compound, C21H21N3O2, was obtained following a five-step synthetic procedure yielding weakly diffracting rod and needle-shaped crystals which crystallized concomitantly. Structural analysis of a rod-shaped crystal showed that the central seven-membered heterocyclic ring adopts a conformation that is perhaps best described as a distorted boat, with the H-bearing (CH2 and NH) atoms lying well out of the least-squares mean plane fitted through the other five atoms in the ring (r.m.s. deviation 0.075 Å). In the crystal, the compound packs as a twisted chain, which propagates along the b axis by means of an R 12(6) motif formed by one of the carbonyl O atoms acting as a bifurcated acceptor in an N - H⋯O and C - H⋯O inter-action. No diffraction was observed from the needle-shaped crystals.

KW - Data-to-parameter ratio = 11.4

KW - Mean σ(C-C) = 0.004 Å

KW - R factor = 0.065

KW - Single-crystal X-ray study

KW - T = 100 K

KW - WR factor = 0.181

UR - http://www.scopus.com/inward/record.url?scp=77949364498&partnerID=8YFLogxK

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U2 - 10.1107/S1600536810005477

DO - 10.1107/S1600536810005477

M3 - Article

C2 - 21580382

AN - SCOPUS:77949364498

SN - 1600-5368

VL - 66

SP - o625

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 3

ER -

2-Butyl-11-phenyl-5,10-dihydro-1H-benzo[e]imidazo[1,5-a][1,4]diazepine-1, 3(2H)-dione

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 770013: Experimental Crystal Structure Determination

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2-Butyl-11-phenyl-5,10-dihydro-1H-benzo[e]imidazo[1,5-a][1,4]diazepine-1, 3(2H)-dione

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

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Datasets

CCDC 770013: Experimental Crystal Structure Determination

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