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(Z)-3-(9-Anthr-yl)-1-(2-thien-yl)prop-2-en-1-one.

ABSTRACT: There are two crystallographically independent mol-ecules in the asymmetric unit of the title heteroaryl chalcone, C(21)H(14)OS: the dihedral angle between the thio-phene and anthracene rings is 75.07 (17)° in one mol-ecule and 76.32 (17)° in the other. The crystal structure is consolidated by short C⋯O [3.348 (5)-3.394 (5) Å], C⋯S [3.607 (5)-3.666 (5) Å] and S⋯O [2.926 (3) Å] contacts, as well as by C-H⋯π and π-π inter-actions [Cg⋯Cg = 3.745 (3) Å].

SUBMITTER: Fun HK

PROVIDER: S-EPMC2969873 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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(Z)-3-(9-Anthr-yl)-1-(2-thien-yl)prop-2-en-1-one.

Fun Hoong-Kun HK Suwunwong Thitipone T Boonnak Nawong N Chantrapromma Suchada S

Acta crystallographica. Section E, Structure reports online 20090815 Pt 9

There are two crystallographically independent mol-ecules in the asymmetric unit of the title heteroaryl chalcone, C(21)H(14)OS: the dihedral angle between the thio-phene and anthracene rings is 75.07 (17)° in one mol-ecule and 76.32 (17)° in the other. The crystal structure is consolidated by short C⋯O [3.348 (5)-3.394 (5) Å], C⋯S [3.607 (5)-3.666 (5) Å] and S⋯O [2.926 (3) Å] contacts, as well as by C-H⋯π and π-π inter-actions [Cg⋯Cg = 3.745 (3) Å]. ...[more]

PMID: 21577575

Similar Datasets

A second ortho-rhom-bic polymorph of (Z)-3-(9-anthr-yl)-1-(2-thien-yl)prop-2-en-1-one.

Project description:The title heteroaryl chalcone, C(21)H(14)OS, is a second ortho-rhom-bic polymorph which crystallizes in the space group P2(1)2(1)2(1). The structure was previously reported [Fun et al. (2009 ▶). Acta Cryst. E65, o2168-o2169] in the space group Pna2(1). The bond distances and angles are similar in both structures. In contrast, the overall crystal packing is different from that in the first ortho-rhom-bic Pna2(1) polymorph in which mol-ecules were stacked into columns along the b axis and the thio-phene units of two adjacent columns were stacked in a head to tail fashion. In the present polymorph, mol-ecules are found to dimerize through a weak S⋯S inter-action [3.6513 (7) Å] and these dimers are arranged into sheets parallel to the bc plane. There are no classical hydrogen bonds in the packing which features short C⋯O [3.2832 (2)-3.6251 (9) Å], C⋯S [3.4879 (17)-3.6251 (19) Å] and S⋯O [2.9948 (16) Å] contacts, together with C-H⋯π inter-actions. Similar contacts were found in the other polymorph.

| S-EPMC2979950 | biostudies-literature

(Z)-3-(9-Anthr-yl)-1-(4-methoxy-phen-yl)prop-2-en-1-one.

Project description:The title chalcone derivative, C(24)H(18)O(2), which consists of the substituted 4-methoxy-phenyl and anthracene rings bridged by the prop-2-en-1-one unit, exists in a cis configuration. The mol-ecule is twisted, the inter-planar angle between the benzene and anthracene rings being 69.50 (10)°. The meth-oxy group is coplanar with the attached benzene ring [C-O-C-C angle = 2.9 (3)°]. In the crystal structure, mol-ecules are linked into chains along the a axis by a weak C-H⋯O(enone) inter-action. The chains are stacked along the c axis. A C-H⋯π inter-action involving the benzene ring is observed.

| S-EPMC2971453 | biostudies-literature

(E)-3-Dimethyl-amino-1-(2-thien-yl)prop-2-en-1-one.

Project description:The mol-ecular skeleton of the title mol-ecule, C(9)H(11)NOS, is essentially planar: the thio-phene ring is inclined to the mean plane of the rest non-H atoms by 2.92 (3)°. The crystal packing exhibits no significantly short inter-molecular contacts.

| S-EPMC2977183 | biostudies-literature

(E)-3-(2,4-Dichloro-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

Project description:In the title chalcone derivative, C(13)H(8)Cl(2)OS, the prop-2-en-1-one unit and the thio-phene and 2,4-dichloro-phenyl rings are each essentially planar. The inter-planar angle between the thio-phene and 2,4-dichloro-phenyl rings is 19.87 (6)°. Weak intra-molecular C-H⋯O and C-H⋯Cl inter-actions involving the prop-2-en-1-one unit generate an S(5)S(5) ring motif. In the crystal structure, mol-ecules are linked into head-to-tail zigzag chains along the a axis and adjacent chains are cross-linked. These cross-linked chains are arranged into sheets parallel to the ab plane. The crystal structure is stabilized by weak C-H⋯O, C-H⋯Cl and C-H⋯π inter-actions. A π-π inter-action was also observed with a centroid-centroid distance of 3.6845 (6) Å.

| S-EPMC2960483 | biostudies-literature

(E)-3-(3,4-Dimethoxy-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

Project description:The title compound, C(15)H(14)O(3)S, has two symmetry-independent mol-ecules in the asymmetric unit with almost identical geometry. The dihedral angle between the benzene and thio-phene rings is 1.61 (11)° in one mol-ecule and 7.21 (11)° in the other. In both mol-ecules, C-H⋯O hydrogen bonds generate rings of graph-set motif S(5). The crystal structure is stabilized by C-H⋯O hydrogen bonds, C-H⋯π inter-actions and π-π inter-actions involving the benzene and thio-phene rings, with centroid-centroid distances of 3.5249 (13) and 3.6057 (13) Å.

| S-EPMC2962071 | biostudies-literature

(E)-1-(2-Thien-yl)-3-(2,4,5-trimethoxy-phen-yl)prop-2-en-1-one.

Project description:In the title mol-ecule, C(16)H(16)O(4)S, the enone fragment, thio-phene ring and benzene ring are individually essentially planar. The thio-phene ring is disordered over two sites, corresponding to a rotation of approximately 180° about the single C-C bond to which it is attached. The approximate ratio of occupancies for the major and minor components is 0.872 (2):0.128 (2). The major component of the thio-phene ring and the benzene ring are twisted from each other by 13.92 (19)°. An intra-molecular C-H⋯O hydrogen bond generates an S(5)S(5) ring motif. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen-bonding inter-actions. In addition, a π-π stacking inter-action, with a centroid-centroid distance of 3.852 (2) Å, and short S⋯O [2.9378 (12) Å] and O⋯O [2.5811 (16) Å] contacts are observed.

| S-EPMC2962137 | biostudies-literature

(E)-3-(4-Chloro-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

Project description:The title compound, C(13)H(9)ClOS, adopts an E configuration with respect to the C=C double bond of the propenone unit. The thienyl and benzene rings are slightly twisted from each other, making a dihedral angle of 6.38 (3)°. An intra-molecular C-H⋯O hydrogen bond generates an S(5) ring motif. A weak inter-molecular C-H⋯O inter-action, a short intra-molecular S⋯O contact [2.932 (2) Å] and two π-π inter-actions between the thienyl and benzene rings are observed. The centroid-centroid distances of the π-π inter-actions are 3.7899 (16) and 3.7891 (16) Å.

| S-EPMC2962207 | biostudies-literature

(E)-1-(2-Thien-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one.

Project description:The mol-ecule of the title heteroaryl chalcone, C(16)H(16)O(4)S, which consists of substituted thio-phene and benzene rings bridged by the prop-2-en-1-one group, is slightly twisted. The dihedral angle between the thio-phene and 3,4,5-trimethoxy-phenyl rings is 12.18 (4)°. The three meth-oxy groups have two different conformations; two meth-oxy groups are coplanar [C-O-C-C torsion angles = -1.38 (12) and 0.47 (12)°] whereas the third is (-)-synclinal with the benzene ring. In the crystal structure, adjacent mol-ecules are linked in a face-to-side manner into chains along the c axis by weak C-H⋯O(enone) inter-actions. These chains are stacked along the b axis by weak C-H⋯O(meth-oxy) inter-actions.

| S-EPMC2969210 | biostudies-literature

3-(2-Chloro-6-fluoro-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

Project description:The title chalcone derivative, C(13)H(8)ClFOS, crystallized as an inversion twin with two independent mol-ecules in the asymmetric unit. The thio-phene rings in both mol-ecules are disordered over two sites: the ratios of occupancies for the major and minor components in the two mol-ecules are 0.820 (2):0.180 (2) and 0.853 (2):0.147 (2). The dihedral angles between the major and minor components of the thio-phene and benzene rings are 1.13 (18) and 2.2 (6)°, respectively, in one mol-ecule, with corresponding values 6.09 (17) and 1.3 (6)° in the other. Weak intra-molecular C-H⋯O and C-H⋯F inter-actions involving the prop-2-en-1-one group generate an S(5)S(5) ring motif, whereas a weak intra-molecular C-H⋯Cl contact generates an S(6) ring motif. In the crystal structure, mol-ecules of both the major and minor components are linked into infinite one-dimensional chains along the b axis. The crystal structure is stabilized by weak C-H⋯O, C-H⋯F, C-H⋯Cl and C-H⋯π inter-actions.

| S-EPMC2960501 | biostudies-literature

(2E)-1-(4-Amino-phen-yl)-3-(2-thien-yl)prop-2-en-1-one ethanol hemisolvate.

Project description:In the title compound, C(13)H(11)NOS·0.5C(2)H(6)O, the chalcone derivative is close to planar, the dihedral angle between the thio-phene and 4-amino-phenyl rings being 3.1 (2)°. The thio-phene ring is disordered over two orientations with occupancies of 0.842 (3) and 0.158 (3). In the crystal structure, mol-ecules are linked into chains along the b axis by N-H⋯O hydrogen bonds. The chains are crosslinked via N-H⋯π inter-actions involving the thio-phene ring. The ethanol solvent mol-ecule is also disordered over two positions, each with an occupancy of 0.25.

| S-EPMC2970323 | biostudies-literature

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