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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.

ABSTRACT: 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)°.

SUBMITTER: El-Hiti GA

PROVIDER: S-EPMC3772474 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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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.

El-Hiti Gamal A GA Smith Keith K Masmali Ali A Balakit Asim A AA Kariuki Benson M BM

Acta crystallographica. Section E, Structure reports online 20130608 Pt 7

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 d ...[more]

PMID: 24046617

Similar Datasets

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-{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

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.

Project description: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.

| S-EPMC3247444 | biostudies-literature

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

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

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

2-[(5-Methyl-thio-phen-2-yl)methyl-idene]malono-nitrile.

Project description:There are two independent molecules in the asymmetric unit of the title compound, C9H6N2S, which is an inter-mediate compound of a cardiovascular drug. The two molecules are nearly planar, displaying dihedral angles of 3.5 (2) and 5.7 (2)° between the thiophene ring and the malononitrile moiety. In the crystal, C-H⋯N inter-actions lead to the formation of a sheet structure that packs in a parallel fashion.

| S-EPMC3772448 | 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

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

(E)-3-(4-Bromo-5-methyl-thio-phen-2-yl)acrylo-nitrile.

Project description:In the title structure, C8H6BrNS, the molecules are planar with the exception of the methyl H atoms. In the crystal, molecules are linked by intermolecular C-H?N interactions to form ribbons parallel to the b axis. Groups of ribbons are arranged in a herringbone pattern to form a layered structure parallel to the ab plane.

| S-EPMC3884493 | biostudies-literature

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