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 journalArticle

2 Citations (Scopus)

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 languageEnglish (US)
JournalActa Crystallographica Section E: Structure Reports Online
Volume66
Issue number3
DOIs
StatePublished - 2010

Fingerprint

Dione
Crystals
needles
Needles
Atoms
crystals
Bearings (structural)
rods
atoms
rings
boats
Boats
structural analysis
Structural analysis
Conformations
Diffraction
deviation
diffraction

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

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

Cite this

2-Butyl-11-phenyl-5,10-dihydro-1H-benzo[e]imidazo[1,5-a][1,4]diazepine-1, 3(2H)-dione. / Nichol, Gary S.; Gunawan, Steven; Dietrich, Justin; Hulme, Christopher.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 66, No. 3, 2010.

Research output: Contribution to journalArticle

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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.",
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AU - Nichol, Gary S.

AU - Gunawan, Steven

AU - Dietrich, Justin

AU - Hulme, Christopher

PY - 2010

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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

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