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5',6-Dichloro-1',3',3'-trimethyl-spiro-[2H-1-benzopyran-2,2'-indoline].

ABSTRACT: In the crystal structure of the title compound, C(19)H(17)Cl(2)NO, the indoline and benzopyran ring systems are approximately perpendicular to each other. The indoline ring is in an envelope conformation with the spiro C atom as the flap. The N atom of the indoline ring forms a pyramidal environment, the sum of the angles at this atom being 352.46°.

SUBMITTER: Alhashimy N

PROVIDER: S-EPMC2962063 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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5',6-Dichloro-1',3',3'-trimethyl-spiro-[2H-1-benzopyran-2,2'-indoline].

Alhashimy Nameer N Müller-Bunz Helge H Schazmann Benjamin B Diamond Dermot D

Acta crystallographica. Section E, Structure reports online 20080709 Pt 8

In the crystal structure of the title compound, C(19)H(17)Cl(2)NO, the indoline and benzopyran ring systems are approximately perpendicular to each other. The indoline ring is in an envelope conformation with the spiro C atom as the flap. The N atom of the indoline ring forms a pyramidal environment, the sum of the angles at this atom being 352.46°. ...[more]

PMID: 21203147

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Crystal structure determination as part of an undergraduate laboratory experiment: 1',3',3'-tri-methyl-spiro-[chromene-2,2'-indoline] and 1',3',3'-trimethyl-4-[(<i>E</i>)-(1,3,3-tri-methyl-indolin-2-yl-idene)meth-yl]spiro-[chroman-2,2'-indoline].

Project description:The crystal structures of the title compounds, C19H19NO and C31H34N2O, were determined as part of an experiment in an undergraduate teaching laboratory that demonstrates the relationship between mol-ecular structure and function. 1',3',3'-Tri-methyl-spiro-[chromene-2,2'-indoline] is both a photoswitch and thermochromic mol-ecule. Students synthesized it and a bis-indoline adduct and compared the crystallographically determined structures to computed gas-phase models.

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1'-Methyl-2,2''-dioxoindoline-3-spiro-2'-pyrrolidine-3'-spiro-3''-indoline-4',4'-di-carbonitrile.

Project description:In the title compound, C(21)H(15)N(5)O(2), the pyrrolidine ring adopts a twist conformation. Both the oxindole rings are planar [maximum deviations of 0.076 (1) and 0.029 (1) Å in the two rings] and are oriented at a dihedral angle of 72.7 (1)°. The crystal structure is stabilized by C-H⋯O, N-H⋯O, N-H⋯N and C-H⋯π inter-actions.

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2'-Eth-oxy-1,3,3-trimethyl-spiro-[indoline-2,3'-3H-naphtho-[2,1-b][1,4]oxazine].

Project description:In the title compound, C(24)H(24)N(2)O(2), the five-membered ring of the indoline ring system adopts an envelope conformation with the spiro C atom at the flap. The dihedral angle between the benzene ring of the indoline ring system and the naphthalene ring system is 71.70 (7)°. In the crystal structure, pair of weak C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

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Project description:In the title compound, C(23)H(23)Cl(2)N(3)O(2), the pyrroline ring adopts an envelope conformation and the piperidinone ring assumes a slightly twisted chair form. In the crystal, inversion dimers linked by pairs of N-H?O hydrogen bonds generate an R(2) (8) graph-set motif and a short Cl?Cl contact of 3.478?(1)?Å occurs.

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1'-Phenyl-6'-thia-cyclo-heptane-1-spiro-2'-perhydro-pyrrolizine-3'-spiro-3''-indoline-2,2''-dione.

Project description:The thia-zolidine ring and the pyrrolidine ring in the title compound, C(25)H(26)N(2)O(2)S, both adopt an envelope conformation. The seven-membered ring has a twist-chair conformation. The crystal packing is stabilized by inter-molecular N-H⋯O hydrogen bonds.

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Methyl 5''-chloro-1',1''-dimethyl-2,2''-dioxodi-spiro-[indoline-3,2'-pyrrolidine-3',3''-indoline]-4'-carboxyl-ate.

Project description:In the title compound, C22H20ClN3O4, the central pyrrolidine ring adopts an envelope conformation on the N atom. The indolinone systems are individually roughly planar, with maximum deviations from their mean planes of 0.130 Å for the spiro C atom of the indolinone unit and 0.172 Å for the carbonyl C atom of the 5-chloro-1-methyl-indolinone unit. They make dihedral angles of 77.7 (8) and 86.1 (8)° with the mean plane through the central pyrrolidine ring. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds supported by C-H⋯O contacts into chains along the ab diagonal. The structure also features C-H⋯O hydrogen bonds, forming R 2 (2)(8) and R 2 (2)(16) rings and generating a three-dimensional array.

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1',3',3'-Trimethyl-2,3-diphenyl-2,3-di-hydro-isoxazole-5(4H)-spiro-2'-indoline.

Project description:Two diastereoisomers of the title compound, C(25)H(26)N(2)O, have been prepared by cyclo-addition between 1,3,3-trimethyl-2-methyl-eneindoline and C-phenyl-N-phenyl-nitrone. The stereochemistry of the major diastereoisomer, viz. S,R/R,S, is confirmed by the X-ray analysis. The oxazole and the pyrole rings have envelope conformations. The packing is stabilized by weak C-H?? inter-actions involving the phenyl ring attached to the N atom of the oxazole and the phenyl ring of the indole fragment.

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1',6-Dimethyl-4'-phenyl-dispiro-[1-benzopyran-3(4H),3'-pyrrolidine-2',3''-indoline]-2,2''-dione.

Project description:In the title compound, C(27)H(24)N(2)O(3), the five-membered pyrroldine ring adopts an envelope conformation (with the N atom in the flap position) and the six-membered pyran-one ring of the coumarine ring system adopts a slightly distorted boat conformation. The oxindole unit makes dihedral angles of 89.7 (1) and 25.6 (1)°, respectively, with the pyrrolidine ring and the coumarin ring system. The mol-ecular structure is stabilized by two intra-molecular C-H⋯O contacts and two intra-molecular π-π inter-actions [centroid-centroid seperations of 3.514 (1) and 3.623 (1) Å]. The crystal packing features N-H⋯O hydrogen bonds, which link the mol-ecules into cyclic centrosymmetric R(2) (2)(8) dimers, and C-H⋯π inter-actions.

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5-Chloro-spiro-[indoline-3,7'-6H,7H,8H-pyrano[3,2-c:5,6-c']di[1]benzopyran]-2,6',8'-trione.

Project description:The asymmetric unit of the title compound, C(26)H(12)ClNO(6), consists of two independent mol-ecules. The central pyran rings and both the 1-benzopyran ring systems are nearly planar in both mol-ecules [r.m.s. deviations of pyan rings = 0.0264?(1) and 0.0326?(1)?Å for molecules A and B, respectively; r.m.s. deviations of benzopyran rings = 0.0439?(1) and 0.0105?(1) for molecule A, 0.0146?(1) and 0.0262?(1)?Å for molecule B]. In the crystal, the molecules are linked by C-H?O, N-H?O and C-H?? inter-actions.

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1'-Methyl-4'-(4-methyl-phen-yl)dispiro-[1-benzopyran-3(4H),3'-pyrrolidine-2',3''-indoline]-2,2''-dione.

Project description:In the title compound, C(27)H(24)N(2)O(3), the pyrroldine ring adopts a twist conformation, while the six-membered pyran-one ring of the coumarin ring system is in a sofa conformation. In the crystal, pairs of N-H?O hydrogen bonds link the mol-ecules into inversion R(2) (2)(8) dimers. These dimers are further connected via C-H?O hydrogen bonds.

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