1,3,3-Trimethylindoline-2-spiro-2'-3'-methyl-2'<i>H</i>-phenanthro[9,10-<i>b</i>][1,4]oxazine

Liang, Y.-C.; Chen, X.-A.; Zhao, Ling; Zhang, Q.-Y.; Chen, J.-X.; Ming, YF; Fan, Mengjiao

doi:10.1107/s0108270197014637

Acta Crystallogr C

1998

DOI: 10.1107/s0108270197014637

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1,3,3-Trimethylindoline-2-spiro-2'-3'-methyl-2'H-phenanthro[9,10-b][1,4]oxazine

Y.-C. Liang¹,

X.-A. Chen²,

Ling Zhao³

et al.

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ChemInform Abstract: 1,3,3‐Trimethylindoline‐2‐spiro‐2′‐3′‐methyl‐2′H‐phenanthro[9,10‐b] [1,4]oxazine.

Liang¹,

Chen²,

Zhao³

et al. 1998

ChemInform

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structure structure (organic substances) K 9000 25 -048 1,3,3-Trimethylindoline-2-spiro-2'-3'-methyl-2'H-phenanthro[9,10-b] [1,4]oxazine.-In the novel photochromic title compound (I) the benzo and phenanthro ring are essentially planar, the pyrrolo ring has a deformed envelope conformation, and the oxazino ring adopts an approximately half-chair conformation. The crystal packing is stabilized by weak C-H···N interactions. -(LIANG, Y.-C.; CHEN, X.-A.; ZHAO, L.; ZHANG, Q.-Y.; CHEN, J.-X.; MING, Y.-F.; FAN, M.-G.; Acta Crystallogr., Sect. C: Cryst.

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ChemInform Abstract: 1,3,3‐Trimethylindoline‐2‐spiro‐2′‐3′‐methyl‐2′H‐phenanthro[9,10‐b] [1,4]oxazine.

Liang¹,

Chen²,

Zhao³

et al. 1998

ChemInform

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Ultrafast dynamics of photoinduced ring-opening and the subsequent ring-closure reactions of spirooxazines in crystalline state

Suzuki

Asahi

Takahashi

et al. 2003

Chemical Physics Letters

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5′-Nitro-1,4-dihydrospiro[3,1-benzoxazine-2,3′-indolin]-2′-one

et al. 2018

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In the title compound, C15H11N3O4, the six-membered oxazine ring adopts a half-chair conformation and is oriented at an angle of 78.63 (9)° with respect to the pyrrolidine ring of the indoline ring system, which adopts an envelope conformation. The spiro centre C atom is tetrahedral and lies 0.147 (1) Å out of the plane of other four pyrrolidone ring atoms. The nitrobenzene and benzene rings exhibit near planar conformations with C—C—C—N and C—C—C—C torsion angles of 178.1 (2) and 178.8 (2)°, respectively. In the crystal, N—H...O and C—H...O hydrogen bonds connect the molecules, generating a sheet-like structure parallel to the bc plane. Within the sheets, pairs of intermolecular N—H...O hydrogen bonds form inversion dimers enclosing R 2 2(8) ring motifs. In addition, the N—H...O and C—H...O hydrogen bonds generate R 3 2(11) and R 2 2(10) graph-set ring motifs extending the two-dimensional structure. A supramolecular R 6 6(28) loop for each set of six molecules is formed by N—H...O hydrogen bonds within the extended sheet structure and stabilizes the packing. π–π stacking interactions between the nitrobenzene and benzene rings [intercentroid distance = 3.711 (1) Å] and N—O...π interactions further consolidate the crystal packing.

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1,3,3-Trimethylindoline-2-spiro-2'-3'-methyl-2'H-phenanthro[9,10-b][1,4]oxazine

Cited by 3 publications

References 2 publications

ChemInform Abstract: 1,3,3‐Trimethylindoline‐2‐spiro‐2′‐3′‐methyl‐2′H‐phenanthro[9,10‐b] [1,4]oxazine.

ChemInform Abstract: 1,3,3‐Trimethylindoline‐2‐spiro‐2′‐3′‐methyl‐2′H‐phenanthro[9,10‐b] [1,4]oxazine.

Ultrafast dynamics of photoinduced ring-opening and the subsequent ring-closure reactions of spirooxazines in crystalline state

5′-Nitro-1,4-dihydrospiro[3,1-benzoxazine-2,3′-indolin]-2′-one

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