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Ethyl 2-amino-4-(3-nitro-phen-yl)-4H-1-benzothieno[3,2-b]pyran-3-carboxyl-ate.

ABSTRACT: The mol-ecule of the title compound, C20H16N2O5S, is built up by one fused five-membered and two fused six-membered rings linked to eth-oxy-carbonyl and 3-nitro-phenyl groups. The benzothieno-pyran ring system is nearly planar (r.m.s deviation = 0.0392?Å) and forms a dihedral angle of 86.90?(6)° with the aromatic ring of the nitro-benzene group. In the crystal, mol-ecules are linked by N-H?O hydrogen bonds and by ?-? inter-actions between the phenyl ring and the six-membered heterocyle [inter-centroid distance = 3.5819?(8)?Å], forming a three-dimensional network.

SUBMITTER: Bakhouch M

PROVIDER: S-EPMC4011203 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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Ethyl 2-amino-4-(3-nitro-phen-yl)-4H-1-benzothieno[3,2-b]pyran-3-carboxyl-ate.

Bakhouch Mohamed M Al Houari Ghali G El Yazidi Mohamed M Saadi Mohamed M El Ammari Lahcen L

Acta crystallographica. Section E, Structure reports online 20140418 Pt 5

The mol-ecule of the title compound, C20H16N2O5S, is built up by one fused five-membered and two fused six-membered rings linked to eth-oxy-carbonyl and 3-nitro-phenyl groups. The benzothieno-pyran ring system is nearly planar (r.m.s deviation = 0.0392 Å) and forms a dihedral angle of 86.90 (6)° with the aromatic ring of the nitro-benzene group. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds and by π-π inter-actions between the phenyl ring and the six-membered heterocyle [inter-ce ...[more]

PMID: 24860386

Similar Datasets

Crystal structure of ethyl 2-amino-4-(4-chloro-phen-yl)-4H-1-benzothieno[3,2-b]pyran-3-carboxyl-ate.

Project description:The title compound, C20H16ClNO3S, is built up from three fused rings, one five- and two six-membered rings, linked to a 3-eth-oxy-carbonyl group and to a 4-chloro-phenyl ring. The hydropyran ring has a flattened envelope conformation, with the C atom substituted by the 4-chloro-phenyl ring as the flap (displaced by 0.077 (2) Å from the plane through the other atoms). The fused three-ring system is quasi-planar (r.m.s. deviation = 0.057 Å), with the largest deviation from the mean plane being 0.106 (1) Å for the C atom substituted by the 4-chloro-phenyl ring. The 4-chloro-phenyl ring is approximately perpendicular to the mean plane of the fused ring system, as indicated by the dihedral angle of 77.32 (6)° between their mean planes. There is an intra-molecular N-H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(12) ring motif. There are also short inter-molecular Cl⋯O inter-actions present [3.1226 (12) Å] between neighbouring mol-ecules.

| S-EPMC4571428 | biostudies-literature

Crystal structure of ethyl 2-amino-4-(4-meth-oxy-phen-yl)-4H-1-benzothieno[3,2-b]pyran-3-carboxyl-ate.

Project description:The mol-ecule of the title compound, C21H19NO4S, features a fused ring system whereby a five-membered ring is flanked by two six-membered rings. This is linked to an ethyl 3-carboxyl-ate group and to a meth-oxy-benzene group. The fused-ring system is quasi-planar, with the greatest deviation from the mean plane being 0.131?(1)?Å for the methine C atom. The plane through the meth-oxy-benzene ring is nearly perpendicular to that through the fused-ring system, as indicated by the dihedral angle of 85.72?(6)°. An intra-molecular N-H?O hydrogen bond is noted. In the crystal, mol-ecules are linked by N-H?O hydrogen bonds, forming layers that stack along the a axis.

| S-EPMC4420120 | biostudies-literature

Ethyl 2-amino-4-phenyl-4H-1-benzo-thieno[3,2-b]pyran-3-carboxyl-ate.

Project description:The title heterocyclic compound, C(20)H(17)NO(3)S, was synthesized by condensation of ethyl cyano-acetate with (Z)-2-benzyl-idenebenzo[b]thio-phen-3(2H)-one in the presence of a basic catalyst in ethanol. The phenyl and ester groups make dihedral angles of 77.67?(6) and 8.52?(6)°, respectively, with the benzothienopyran ring system [maximum r.m.s. deviation = 0.1177?(13)?Å]. In the crystal, centrosymmetric dimers are formed through pairs of N-H?O hydrogen bonds between the amine and ester groups. Inter-molecular C-H?N hydrogen bonds and C-H?? inter-actions involving the thio-phene ring are also observed.

| S-EPMC3213548 | biostudies-literature

Ethyl 6-amino-5-cyano-2,4-bis-(4-methyl-phen-yl)-4H-pyran-3-carboxyl-ate.

Project description:In the title compound, C(23)H(22)N(2)O(3), the pyran ring adopts a twisted boat conformation. The tolyl rings and carboxyl-ate group are attached to the pyran ring with torsion angles of -77.1?(2), 59.5?(3) and 17.8?(3)°, respectively. The ethyl group is disordered over two orientations with a site-occupancy ratio of 0.508?(5):0.492?(5). In the crystal, mol-ecules are linked by N-H?N and N-H?O hydrogen bonds, generating a chain running the a axis. Weak C-H?O, C-H?N and C-H?? inter-actions are also observed.

| S-EPMC2983318 | biostudies-literature

Ethyl 6-amino-5-cyano-4-isopropyl-2-methyl-4H-pyran-3-carboxyl-ate.

Project description:In the title compound, C(13)H(18)N(2)O(3), the two H atoms of the NH(2) group are engaged in hydrogen bonding with the N atom of the cyano group and with one O atom of the ethoxy-carbonyl group, building a chain parallel to the [100] direction. The N-H⋯N hydrogen bonds assemble the mol-ecules around inversion centres, forming dimers with an R(2) (2)(12) graph-set motif.

| S-EPMC2967956 | biostudies-literature

Ethyl 6-amino-5-cyano-2-methyl-4-propyl-4H-pyran-3-carboxyl-ate.

Project description:The pyran ring of the title compound, C(13)H(18)N(2)O(3), is almost planar (r.m.s. deviation = 0.059?Å). The crystal packing is stabilized by N-H?O and N-H?N hydrogen bonds.

| S-EPMC2971089 | biostudies-other

Ethyl 5-amino-1-(4-chloro-2-nitro-phen-yl)-1H-pyrazole-4-carboxyl-ate.

Project description:In the mol-ecule of the title compound, C(12)H(11)ClN(4)O(4), the pyrazole ring is coplanar with the amino and ethoxy-carbonyl groups within 0.026?(2) and 0.105?(2)?Å, respectively. The C(6) ring of the 4-chloro-2-nitro-phenyl group is twisted by 53.58?(4)° relative to the plane of the pyrazole ring. The planar structure of the pyrazole ring is stabilized by an intra-molecular N-H?O hydrogen bond between its substituents. Neighbouring mol-ecules are linked through inter-molecular N-H?N and N-H?O hydrogen bonds, giving rise to one-dimensional tapes along the b axis. Mol-ecules in the chain are linked to those of an adjacent chain through weak C-H?O inter-actions, forming a three-dimensional network.

| S-EPMC2968147 | biostudies-literature

Crystal structures of ethyl 6-(4-methyl-phen-yl)-4-oxo-4H-chromene-2-carboxyl-ate and ethyl 6-(4-fluoro-phen-yl)-4-oxo-4H-chromene-2-carboxyl-ate.

Project description:The crystal structures of two chromone derivatives, viz. ethyl 6-(4-methyl-phen-yl)-4-oxo-4H-chromene-2-carboxyl-ate, C19H16O4, (1), and ethyl 6-(4-fluoro-phen-yl)-4-oxo-4H-chromene-2-carboxyl-ate C18H13FO4, (2), have been determined: (1) crystallizes with two mol-ecules in the asymmetric unit. A comparison of the dihedral angles beween the mean planes of the central chromone core with those of the substituents, an ethyl ester moiety at the 2-position and a para-substituted phenyl ring at the 6-position shows that each mol-ecule differs significantly from the others, even the two independent mol-ecules (a and b) of (1). In all three mol-ecules, the carbonyl groups of the chromone and the carboxyl-ate are trans-related. The supra-molecular structure of (1) involves only weak C-H?? inter-actions between H atoms of the substituent phenyl group and the phenyl group, which link mol-ecules into a chain of alternating mol-ecules a and b, and weak ?-? stacking inter-actions between the chromone units. The packing in (2) involves C-H?O inter-actions, which form a network of two inter-secting ladders involving the carbonyl atom of the carboxyl-ate group as the acceptor for H atoms at the 7-position of the chromone ring and from an ortho-H atom of the exocyclic benzene ring. The carbonyl atom of the chromone acts as an acceptor from a meta-H atom of the exocyclic benzene ring. ?-? inter-actions stack the mol-ecules by unit translation along the a axis.

| S-EPMC4704759 | biostudies-literature

Ethyl 1-benzyl-5-{[(isopropyl-amino)(3-nitro-phen-oxy)methyl-idene]amino}-1H-1,2,3-triazole-4-carboxyl-ate.

Project description:In the title compound, C(22)H(24)N(6)O(5), the triazole ring is essentially planar with a maximum deviation of 0.005?(2)?Å and forms dihedral angles of 79.78?(11) and 86.22?(11)° with the phenyl and benzene rings, respectively. In the crystal, mol-ecules are linked by inter-molecular N-H?N, C-H?O and C-H?? inter-actions into a three-dimensional network.

| S-EPMC3011645 | biostudies-literature

Ethyl 5-(4-amino-phen-yl)isoxazole-3-carboxyl-ate.

Project description:The asymmetric unit of the title compound, C(12)H(12)N(2)O(3), contains two mol-ecules in which the benzene and isoxazole rings are almost coplanar, the dihedral angles between their mean planes being 1.76?(9) and 5.85?(8)°. The two mol-ecules inter-act with each other via N-H?N and N-H?O hydrogen bonds, which link the mol-ecules into layers parallel to the ac plane. The layers stack in a parallel mode with an inter-layer distance of 3.36?(7)?Å.

| S-EPMC3344059 | biostudies-literature

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