Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

2-(1,2-Dimethyl-1H-indol-3-yl)-1-{5-[3-(1,3-dioxolan-2-yl)phen-yl]-2-methyl-thio-phen-3-yl}-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-ene.

ABSTRACT: The title compound, C(29)H(23)F(6)NO(2)S, a member of a new family of photochromic diaryl-ethene compounds having an unsymmetrically substituted hexa-fluoro-cyclo-pentene unit, displays dihedral angles between the indole and thio-phene rings of 52.5?(4)°, and between the indole ring and the planar C-C=C-C unit of the cyclopentene ring of 53.8?(6)°. The distance between the potentially reactive C atoms from the two heteroaryl substituents of 3.817?(6)?Å is proven to be short enough for photocyclization to occur.

SUBMITTER: Wang LQ

PROVIDER: S-EPMC3247444 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

2-(1,2-Dimethyl-1H-indol-3-yl)-1-{5-[3-(1,3-dioxolan-2-yl)phen-yl]-2-methyl-thio-phen-3-yl}-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-ene.

Wang Li-Qin LQ Yan Liu-Shui LS Liu Gang G

Acta crystallographica. Section E, Structure reports online 20111029 Pt 11

The title compound, C(29)H(23)F(6)NO(2)S, a member of a new family of photochromic diaryl-ethene compounds having an unsymmetrically substituted hexa-fluoro-cyclo-pentene unit, displays dihedral angles between the indole and thio-phene rings of 52.5 (4)°, and between the indole ring and the planar C-C=C-C unit of the cyclopentene ring of 53.8 (6)°. The distance between the potentially reactive C atoms from the two heteroaryl substituents of 3.817 (6) Å is proven to be short enough for photocycli ...[more]

PMID: 22220062

Similar Datasets

1-[5-(3-Chloro-phen-yl)-2-methyl-3-thi-en-yl]-3,3,4,4,5,5-hexa-fluoro-2-(2-methoxy-phen-yl)-cyclo-pent-1-ene.

Project description:The title compound, C(23)H(15)ClF(6)OS, has thienyl and phenyl-ene substituents on the double-bond C atoms of the envelope-shaped cyclo-pentenyl ring. The aromatic systems are aligned at 55.3 (4) (thien-yl) and 60.8 (7)° (phenyl-ene) with respect to the planar C-C=C-C portion of the main central cyclo-pentenyl ring.

| S-EPMC2977783 | biostudies-literature

4-{2-[5-(3,5-Difluoro-phen-yl)-2-methyl-thio-phen-3-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-en-1-yl}-1,5-dimethyl-pyrrole-2-carbonitrile.

Project description:In the title compound, C(23)H(14)F(8)N(2)S, the dihedral angles between the pyrrole and thio-phene groups and the almost planar C-C=C-C unit of the cyclo-pentene ring (r.m.s. deviation = 0.4193?Å) are 43.6?(5) and 50.1?(2)°, respectively. The distance of 3.612?(3)?Å between the potentially reactive C atoms of the two heteroaryl substituents is short enough to enable a photocyclization reaction.

| S-EPMC3099757 | biostudies-literature

1,2-Bis[5-(4-cyano-phen-yl)-2-methyl-3-thien-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-ene: a photochromic diaryl-ethene compound.

Project description:The mol-ecules of the title compound, C(29)H(16)F(6)N(2)S(2), a photochromic dithienylethene with 4-cyano-phenyl substituents, adopt an anti-parallel arrangement that is reponsible for photoactivity. The mol-ecule lies on a twofold rotation axis. The dihedral angle between the nearly planar cyclo-pentenyl and heteroaryl rings is 142.5 (3)°, and that between the heteroaryl and benzene rings is 22.4 (3)°. The distance between the heteroaryl rings of adjacent mol-ecules is 3.601 (2) Å, indicating a π-π interaction.

| S-EPMC2961168 | biostudies-literature

4-(5-{2-[5-(4-Cyano-phen-yl)-3-methyl-thio-phen-2-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-en-1-yl}-4-methyl-thio-phen-2-yl)benzo-nitrile chloro-form hemisolvate.

Project description:The crystal structure of the title compound, C29H16F6N2S2·0.5CHCl3, consists of mol-ecules with disordered perfluoro-cyclo-pentene rings [occupancy ratio 0.685 (3):0.315 (3)] and close F⋯F contacts (in the range 2.45-2.73 Å) between mol-ecules. The short contacts are associated with the disorder. The dihedral angle between thiophene rings is 57.44 (8)°. The 5-(4-cyano-phen-yl)-3-methyl-2-thienyl groups of adjacent mol-ecules are parallel, leading to zigzag chains of mol-ecules along [101]. The dihedral angles between each thiophene ring and its adjacent cyanobenzene ring are 8.9 (2) and 7.15 (10)°.

| S-EPMC3772474 | biostudies-literature

1-(2-Chloro-phen-yl)-2-(2-methyl-5-phenyl-3-thien-yl)-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-ene: a new photochromic diaryl-ethene.

Project description:The title compound, C(22)H(13)ClF(6)S, is a hybrid diaryl-ethene derivative with one 3-thienyl substituent, and a Cl-substituted six-membered aryl unit bonded to the double bond of a hexa-fluoro-cyclo-pentene ring. In the crystal structure, the mol-ecule adopts a photo-active anti-parallel conformation that can undergo effective photocyclization reactions. The distance between the two reactive C atoms is 3.848?(3)?Å. The dihedral angles between the least-squares cyclo-pentene plane and those of the adjacent thio-phene and chloro-phenyl rings are 49.39?(8) and 59.88?(8)°, respectively. The F atoms are disordered over two positions, with site occupancy factors of 0.6 and 0.4.

| S-EPMC2961463 | biostudies-literature

5-n-Butyl-4-[2-(2-ethyl-1-benzothio-phen-3-yl)-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-en-1-yl]thio-phene-2-carbaldehyde.

Project description:The title compound, C(24)H(20)F(6)OS(2), exhibiting photochromic behaviour, has thienyl and benzothienyl substituents attached to the double-bond C atoms of the envelope-shaped cyclo-pentene ring. The mean planes of aromatic systems form dihedral angles of 43.0 (1) (thien-yl) and 73.8 (1)° (benzothien-yl) with the mean plane of the C-C=C-C portion of the cyclo-pentene ring. This conformation avoids steric hindrance between the n-butyl and ethyl substituents. The formyl substituent of the thienyl group, as well as the ethyl substituent of the benzothienyl group, are disordered [occupancies of 0.788 (17):0.212 (17) and 0.64 (5):0.36 (5), respectively].

| S-EPMC2959974 | biostudies-literature

3,3,4,4,5,5-Hexa-fluoro-1,2-bis[4-(phenyl-ethyn-yl)phen-yl]-cyclo-pentene.

Project description:The title compound, C(33)H(18)F(6), has a V-shaped conjugated subunit. The dihedral angles between the central cyclo-pentene ring and the directly attached benzene rings are 32.7?(2) and 53.7?(2)°, respectively. The fluoro substituents are disordered, the occupancies refined to a 0.675?(2):0.325?(2) ratio.

| S-EPMC2980200 | biostudies-literature

1,2-Bis[5-(9-ethyl-9H-carbazol-3-yl)-2-methyl-thio-phen-3-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pentene.

Project description:The title compound, C(43)H(32)F(6)N(2)S(2), is a new symmetrical photochromic diaryl-ethene derivative with 9-ethyl-carbazol-3-yl substituents. The mol-ecule adopts a photoactive anti-parallel conformation [Irie (2000). Chem. Rev.100, 1685-1716; Kobatake et al. (2002). Chem. Commun. pp. 2804-2805], with a dihedral angle between the mean planes of the two thio-phene rings of 56.23?(6)°. The distance between the two reactive C atoms is 3.497?(3)?Å. In the crystal, two mol-ecules are associated through a pair of C-H?F inter-molecular hydrogen bonds, forming a centrosymmetric dimer. Dimers are linked by weak ?-? inter-actions [centroid-centroid distance = 3.8872?(13)?Å], forming chains along the c axis.

| S-EPMC3213625 | biostudies-literature

3,3,4,4,5,5-Hexafluoro-1,2-bis-(5-formyl-2-methylsulfanyl-3-thienyl)cyclo-pent-1-ene.

Project description:In the crystal structure of the title diaryl-ethyl-ene compound, C(17)H(10)F(6)O(2)S(4), the two 3-thienyl substituents are aligned at 44.9 (1) and 40.2 (1)° with respect to the -C-C=C-C- fragment of the central cyclo-pentenyl ring. The five-membered cyclo-pentenyl ring adopts an envelope conformation. The flap atom of this ring and the two F atoms bonded to it are disordered over two positions with occupancies 0.810 (5)/0.190 (5).

| S-EPMC2961574 | biostudies-literature

3-(4-{3,3,4,4,5,5-Hexafluoro-2-[5-(3-methoxy-phen-yl)-2-methyl-3-thien-yl]cyclo-pent-1-en-yl}-5-methyl-2-thien-yl)benzonitrile.

Project description:The title compound, C(29)H(19)F(6)NOS(2), is a new unsymmetrical photochromic diarylethene derivative with different meta-phenyl substituents. The distance between the two reactive (i.e. can be irradiated to form a new chemical bond) C atoms is 3.501?(4)?Å; the dihedral angles between the mean plane of the main central cyclo-pentene ring and the thio-phene rings are 47.7?(5) and 45.1?(2)°, and those between the thio-phene rings and the adjacent benzene rings are 29.4?(2) and 28.4?(3)°. The three C atoms and the F atoms of hexa-fuorocyclo-pentene ring are disordered over two positions, with site-occupancy factors of 0.751?(4) and 0.249?(4).

| S-EPMC2970449 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data