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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.

ABSTRACT: 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].

SUBMITTER: Yang Z

PROVIDER: S-EPMC2959974 | biostudies-literature |

REPOSITORIES: biostudies-literature

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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-Benzothio-phene-2-carbaldehyde 4-ethyl-thio-semicarbazone.

Project description:The title compound, C(13)H(15)N(3)S(2), crystallizes with two unique mol-ecules, A and B, in the asymmetric unit. These differ principally in that the methyl group of the 4-ethyl-thio-semicarbazone moiety is ordered in mol-ecule A but disordered over two positions with equal occupancies in mol-ecule B. The benzothio-phene group and the semicarbazone unit are inclined at dihedral angles of 11.78?(8)° for mol-ecule A and 8.18?(13)° for mol-ecule B. Weak intra-molecular N-H?N inter-actions contribute to the planarity of the semicarbazone units in both mol-ecules and each mol-ecule adopts an E configuration with respect to the C=N bonds. In the crystal structure, mol-ecules form centrosymmetric dimers as a result of N-H?S hydrogen bonds, augmented by C-H?S inter-actions for mol-ecule A and C-H?S inter-actions for mol-ecule B. Weak C-H?? inter-actions stack the dimers of both mol-ecules into columns down the a axis.

| S-EPMC2968090 | biostudies-other

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

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-[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

3-[(2-Formyl-thio-phen-3-yl)(hy-droxy)meth-yl]thio-phene-2-carbaldehyde.

Project description:In the title compound, C(11)H(8)O(3)S(2), the dihedral angle between the mean planes of the two thio-phene rings is 65.10?(10)°. Intra-molecular C-H?O inter-actions form S(6) and S(7) ring motifs. In the crystal, chains along the a axis are formed by C-H?O inter-actions. Adjacent chains are connected into a three-dimensional network by C-H?O and O-H?O inter-actions.

| S-EPMC3254520 | biostudies-literature

Thio-phene-2-carbaldehyde azine.

Project description:The asymmetric unit of the title compound, C10H8N2S2, is composed of two independent half-mol-ecules, each residing on a center of symmetry. In the crystal, weak C-H?? inter-actions join the two symmetry-independent molecules together into interlinked chains parallel to [011]. The crystal structure was refined as a two-component pseudo-merohedral twin using the twin law 001 0-10 100. The refined domain fractions are 0.516?(3) and 0.484?(3).

| S-EPMC3685067 | 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-(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 ?-? interaction.

| S-EPMC2961168 | biostudies-literature

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