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2-[(Z)-4,7-Dichloro-3,3-dimethyl-2,3-dihydro-1H-indol-2-yl-idene]-3-oxopropane-nitrile.

ABSTRACT: In the title compound, C(13)H(10)Cl(2)N(2)O, the ring N atom and its three attached atoms are essentially coplanar with angles adding to 359.8°, indicating conjugation with the 2-formyl-acrylonitrile subunit. The aldehyde group is oriented to place the carbonyl O atom 2.02?(3)?Å from the N-H hydrogen atom. Intra-molecular N-H?O and C-H?Cl inter-actions occur. The geometry of the exocyclic double bond is Z. In the crystal, weak C-H?N hydrogen bonds link the mol-ecules into chains along [1[Formula: see text]0].

SUBMITTER: Helliwell M

PROVIDER: S-EPMC3254565 | biostudies-other | 2012 Jan

REPOSITORIES: biostudies-other

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2-[(Z)-4,7-Dichloro-3,3-dimethyl-2,3-dihydro-1H-indol-2-yl-idene]-3-oxopropane-nitrile.

Helliwell Madeleine M Baradarani Mehdi M MM Mohammadnejadaghdam Razieh R Afghan Arash A Joule John A JA

Acta crystallographica. Section E, Structure reports online 20111223 Pt 1

In the title compound, C(13)H(10)Cl(2)N(2)O, the ring N atom and its three attached atoms are essentially coplanar with angles adding to 359.8°, indicating conjugation with the 2-formyl-acrylonitrile subunit. The aldehyde group is oriented to place the carbonyl O atom 2.02 (3) Å from the N-H hydrogen atom. Intra-molecular N-H⋯O and C-H⋯Cl inter-actions occur. The geometry of the exocyclic double bond is Z. In the crystal, weak C-H⋯N hydrogen bonds link the mol-ecules into chains along [1[Formula ...[more]

PMID: 22259515

Similar Datasets

2-(4-{3-[1-(3-Bromo-prop-yl)-3,3-dimethyl-2,3-dihydro-1H-indol-2-yl-idene]prop-1-en-yl}-3-cyano-5,5-dimethyl-2,5-dihydro-furan-2-yl-idene)malononitrile.

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3,3-Dieth-oxy-5-fluoro-2,3-dihydro-1H-indol-2-one.

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A second monoclinic polymorph of 2-(diformyl-methyl-idene)-3,3-dimethyl-2,3-dihydro-1H-indole.

Project description:The crystal structure of the title compound, C(13)H(13)NO(2), is a polymorph of the structure first reported by Helliwell et al. [Acta Cryst. (2006), E62, o737-o738]. It is also monoclinic (space group P2(1)/c), but with completely different cell constants. The mol-ecular conformations of these polymorphs differ by a 180° rotation of one formyl group. The present mol-ecule is planar [maximum deviation 0.089?(2)?Å] with the exception of the two methyl groups which lie on either side of the plane. There are strong intra- and inter-molecular N-H?O hydrogen bonds. The latter link pairs of mol-ecules across crystallographic centers of symmetry. Two aldehyde O atoms are brought close together [2.896?(4)?Å in this arrangement but are not hydrogen bonded. In the earlier polymorph, one formyl group is rotated by 180° to yield inter-molecular hydrogen bonding and an infinite polymeric chain. The other formyl group is involved in the same intra-molecular hydrogen bonding as has been found here.

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2,2'-Bis(methyl-ene)-3,3'-(2-thioxo-2,3-dihydro-1H-benzimidazole-1,3-di-yl)dipropane-nitrile.

Project description:In the title compound, C(15)H(12)N(4)S, the benzimidazole ring is essentially planar, with a mean deviation of 0.0082?(1)?Å from the least-squares plane defined by the nine constituent atoms. In the crystal, inversion dimers linked by pairs of C-H?N hydrogen bonds occur.

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Project description:The mol-ecule of the title compound, C(14)H(10)FN(3)O(3)S, consists of an indole unit and a phenylsulfonyl unit that are disposed in an approximately trans orientation relative to the N-N single bond. Two mol-ecules are arranged about a center of inversion, forming a hydrazide-carbonyl N-H?O hydrogen-bonded dimer; the dimers are linked by an indole-sulfonyl N-H?O hydrogen bond into a ribbon.

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2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl-idene)-2-cyano-acetamide.

Project description:Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl-idene)propane-dial with hydroxyl-amine gives the title compound, C(14)H(14)ClN(3)O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyano-acryl-amide unit. The orientation of the acetamide group arises from intra-molecular hydrogen bonding between the indole N-H and carbonyl groups. In the crystal, inversion-related acetamide groups form N-H?O hydrogen-bonded dimers in graph-set R(2) (2)(8) motifs, whilst dimers are also formed by pairs of amine-nitrile N-H?N hydrogen bonds in R(2) (2)(12) motifs. These inter-actions together generate ribbons that propagate along the b-axis direction.

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Diethyl 2-oxo-3-(2-oxo-2,3-dihydro-1H-indol-3-yl-idene)butane-dioate.

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2,2-Dimethyl-2,3-dihydro-1H-perimidine.

Project description:The title compound, C(13)H(14)N(2), was obtained from reaction of diaminona-phthalene with acetone. In both independent mol-ecules in the asymmetric unit, the tricyclic perimidine consists of a planar (r.m.s. deviations = 0.0125 and 0.0181?Å) naphthalene ring system and an envelope conformation C(4)N(2) ringwith the NCN group hinged with respect to the naph-thalene backbone by 36.9?(2) and 41.3?(2)° in the two independent molecules. The methyl substituents are arranged approximately axial and equatorial on the apical C atom. In the crystal, one of the N-H groups of one independent mol-ecule is involved in classical N-H?N hydrogen bonding. Short inter-molecular (C/N)-H??(arene) inter-actions, near the short T-shaped limit, link mol-ecules in the absence of strong acceptors.

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(Z)-4-Hexyl-1-(5-nitro-2-oxo-2,3-dihydro-1H-indol-3-yl-idene)thio-semicarbazide.

Project description:In the title compound, C(15)H(19)N(5)O(3)S, intra-molecular N-H?O, N-H?N and C-H?S inter-actions occur and the three terminal C atoms of the hexyl group are disordered over two sites with an occupancy ratio of 0.664?(12):0.336?(12). In the crystal, inversion dimers linked by pairs of N-H?O hydrogen bonds occur and C-H?O bonds link the dimers into chains. A short C=O?? contact is also present.

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5-Methyl-N'-[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-yl-idene]-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide.

Project description:In the title compound, C18H14N6O2, the benzene ring is slightly twisted out of the plane of the 1,2,3-triazole ring (r.m.s. deviation = 0.010?Å), forming a dihedral angle of 6.20?(13)°. The nine non-H ring atoms of the fused five- and six-membered ring system are almost coplanar (r.m.s. deviation = 0.032?Å). The near coplanarity in the central residue is consolidated by an intra-molecular bifurcated N-H?(O,N) hydrogen bond. The conformation about the N=C bond is Z. In the crystal, supra-molecular chains along [101] are sustained by N-H?O hydrogen bonds and C-H?O inter-actions. These are consolidated into a three-dimensional architecture by C-H?? and ?-? inter-actions; the latter occur between centrosymmetrically related 1,2,3-triazole rings [centroid-centroid distance = 3.6056?(14)?Å].

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