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2-(4-Bromo-phen-yl)-2-methyl-2,3-di-hydro-quinazolin-4(1H)-one.

ABSTRACT: In the title compound, C(15)H(13)BrN(2)O, the pyrimidine ring adopts a skew boat conformation. The amino H atom forms an inter-molecular hydrogen bond with the carbonyl O atom of an adjacent mol-ecule, forming an inversion dimer. Another lone pair of electrons on the same carbonyl O atom acts as acceptor for another N-H?O inter-molecular hydrogen bond with a neighbouring mol-ecule, forming chains along the c axis.

SUBMITTER: Zhang MM

PROVIDER: S-EPMC2979070 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

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2-(4-Bromo-phen-yl)-2-methyl-2,3-di-hydro-quinazolin-4(1H)-one.

Zhang Mei-Mei MM Yang Ke K Wang Xiang-Shan XS

Acta crystallographica. Section E, Structure reports online 20100414 Pt 5

In the title compound, C(15)H(13)BrN(2)O, the pyrimidine ring adopts a skew boat conformation. The amino H atom forms an inter-molecular hydrogen bond with the carbonyl O atom of an adjacent mol-ecule, forming an inversion dimer. Another lone pair of electrons on the same carbonyl O atom acts as acceptor for another N-H⋯O inter-molecular hydrogen bond with a neighbouring mol-ecule, forming chains along the c axis. ...[more]

PMID: 21579124

Similar Datasets

Crystal structure of 3-benzyl-2-[(E)-2-(furan-2-yl)ethen-yl]-2,3-di-hydro-quinazolin-4(1H)-one and 3-benzyl-2-[(E)-2-(thio-phen-2-yl)ethen-yl]-2,3-di-hydro-quinazolin-4(1H)-one from synchrotron X-ray diffraction.

Project description:The chiral title compounds, C21H18N2O2, (I), and C21H18N2OS, (II) - products of the three-component reaction between benzyl-amine, isatoic anhydride and furyl- or thienyl-acrolein - are isostructural and form isomorphous racemic crystals. The tetra-hydro-pyrimidine ring in (I) and (II) adopts a sofa conformation. The amino N atom has a trigonal-pyramidal geometry [sum of the bond angles is 347.0° for both (I) and (II)], whereas the amido N atom is flat [sum of the bond angles is 359.3° for both (I) and (II)]. The furyl- and thienylethenyl substituents in (I) and (II) are planar and the conformation about the bridging C=C bond is E. These bulky fragments occupy the axial position at the quaternary C atom of the tetra-hydro-pyrimidine ring, apparently, due to steric reasons. In the crystals, mol-ecules of (I) and (II) form hydrogen-bonded helicoidal chains propagating along [010] by strong inter-molecular N-H⋯O hydrogen bonds.

| S-EPMC5778476 | biostudies-literature

2-(4-Chloro-phen-yl)-2,3-di-hydro-quinolin-4(1H)-one.

Project description:The title mol-ecule, C15H12ClNO, features a di-hydro-quinolin-4(1H)-one moiety attached to a chloro-benzene ring. The heterocyclic ring has a half-chair conformation with the methine C atom lying 0.574 (3) Å above the plane of the five remaining atoms (r.m.s. deviation = 0.0240 Å). The dihedral angles between the terminal benzene rings is 77.53 (9)°, indicating a significant twist in the mol-ecule. In the crystal, supra-molecular zigzag chains along the c-axis direction are sustained by N-H⋯O hydrogen bonds. These are connected into double chains by C-H⋯π inter-actions.

| S-EPMC3998350 | biostudies-literature

Three-component reaction between isatoic anhydride, amine and meth-yl-subs-tituted furyl-acryl-alde-hydes: crystal structures of 3-benzyl-2-[(E)-2-(5-methylfuran-2-yl)vin-yl]-2,3-di-hydro-quinazolin-4(1H)-one, 3-benzyl-2-[(E)-2-(furan-2-yl)-1-methyl-vin-yl]-2,3-di-hydro-quinazolin-4(1H)-one and 3-(furan-2-ylmeth-yl)-2-[(E)-2-(furan-2-yl)-1-methyl-vin-yl]-2,3-di-hydro-quinazolin-4(1H)-one.

Project description:Compounds (I), C22H20N2O2, (II), C22H20N2O2 and (III), C20H18N2O3 are the products of three-component reactions between isatoic anhydride, the corresponding amine and 3-(5-methylfuran-2-yl)- or (furan-2-yl)-2-methyl-acryl-aldehyde. Compound (I) crystallizes in the monoclinic space group P21/n, while compounds (II) and (III) are isostructural and crystallize in the ortho-rhom-bic space group Pbca. The tetra-hydro-pyrimidine ring in (I)-(III) adopts a sofa conformation. The NH nitro-gen atom has a trigonal-pyramidal geometry, whereas the N(R) nitro-gen atom is flattened. The furyl-vinyl substituents in (I)-(III) are practically planar and have an E configuration at the C=C double bond. In (I), this bulky fragment occupies the axial position at the quaternary carbon atom of the tetra-hydro-pyrimidine ring, whereas in (II) and (III) it is equatorially disposed. In the crystal of (I), mol-ecules form hydrogen-bonded chains propagating along [001] by strong inter-molecular N-H⋯O hydrogen bonds. The chains are packed in stacks along the a-axis direction. In the crystals of (II) and (III), mol-ecules also form hydrogen-bonded chains propagating along [100] by strong inter-molecular N-H⋯O hydrogen bonds. However, despite the fact that compounds (II) and (III) are isostructural, steric differences between the phenyl and furyl substituents result in chains with different geometries. Thus in the crystal of (II) the chains have a zigzag-like structure, whereas in the crystal of (III), they are almost linear. In both (II) and (III), the hydrogen-bonded chains are further packed in stacks along the b-axis direction.

| S-EPMC6072988 | biostudies-literature

2-(2-Chloro-phen-yl)-2,3-dihydro-quinazolin-4(1H)-one.

Project description:The title compound, C(14)H(11)ClN(2)O, was synthesized by the reaction of 2-chloro-benzaldehyde and 2-amino-benzamide in an ionic liquid. The pyrimidine ring adopts a skew-boat conformation and the two benzene rings make a dihedral angle of 87.1 (1)°. In the crystal, N-H⋯O and C-H⋯N hydrogen bonding links the mol-ecules along b.

| S-EPMC2970036 | biostudies-literature

2-(Di-phenyl-methyl-idene)-2,3-di-hydro-1H-inden-1-one.

Project description:In the title mol-ecule, C22H16O, the indanone ring system is approximately planar with a dihedral angle between the fused rings of 5.13 (14)°. Two benzene rings are linked together at one side of a double bond, sitting on either side of the indanone ring system and making dihedral angles of 70.30 (12) and 44.74 (13)° with it. In the crystal, hydrogen bonding is not present, but weak C-H⋯π or π-π inter-actions occur and mol-ecules form a sheet-like structure in the bc plane.

| S-EPMC3793795 | biostudies-literature

Crystal structure of 4-[(2,4-di-chloro-phen-yl)(5-hy-droxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)meth-yl]-5-methyl-2-phenyl-2,3-di-hydro-1H-pyrazol-3-one.

Project description:In the title compound C27H22Cl2N4O2, the pyrazol-5-ol ring makes a dihedral angle of 34.80 (11)° with the phenyl ring to which it is bound, while the pyrazolone ring is inclined at 34.34 (12)° to its attached phenyl ring. In the crystal, N-H⋯O and C-H⋯Cl hydrogen bonds link the mol-ecules into chains along [010]. Inter-molecular π-π inter-actions are observed between the pyrazolone ring and the phenyl ring bound to the pyrazol-5-ol ring system [centroid-centroid separation = 3.916 (2) Å].

| S-EPMC4647350 | biostudies-literature

2,3-Di-methyl-quinazolin-4(3H)-one.

Project description:The non-H atoms of the title mol-ecule, C10H10N2O, are essentially coplanar, with a maximum deviation of 0.046?(4)?Å for the O atom. In the crystal, mol-ecules are linked by weak C-H?O hydrogen bonds, forming chains along [010]. In addtion, weak C-H?? inter-actions and ?-? stacking inter-actions between benzene and pyrimidine rings, with a centroid-centroid distance of 3.730?(3)?Å, link the chains, forming a two-dimensional network parallel to (001).

| S-EPMC4120575 | biostudies-literature

(2E)-2-(4-Bromo-benzyl-idene)-2,3-di-hydro-1H-inden-1-one.

Project description:The title indan-1-one derivative, C(16)H(11)BrO, is planar, the r.m.s. deviation for all 18 non-H atoms being 0.071?Å. The configuration about the C=C bond [1.337?(5)?Å] is E. In the crystal, supra-molecular layers in the ab plane are formed by C-H?O inter-actions, involving the bifurcated carbonyl O atom, as well as C-H?? inter-actions. The studied crystal was an inversion twin.

| S-EPMC3295522 | biostudies-literature

6-Bromo-2-[(E)-thio-phen-2-yl-methyl-idene]-2,3,4,9-tetra-hydro-1H-carbazol-1-one.

Project description:In the title compound, C(17)H(12)BrNOS, the cyclo-hexene ring deviates only slightly from planarity (r.m.s. deviation for non-H atoms = 0.047 Å). In the crystal, the mol-ecules are linked into centro-symmetric R(2) (2)(10) dimers via pairs of N-H⋯O hydrogen bonds. The thio-phene ring is disordered over two positions rotated by 180° and with a site-occupation factor of 0.843 (4) for the major occupied site.

| S-EPMC3238929 | biostudies-literature

Crystal structure of (4Z)-1-(3,4-di-chloro-phen-yl)-4-[hy-droxy(4-methyl-phen-yl)methyl-idene]-3-methyl-4,5-di-hydro-1H-pyrazol-5-one.

Project description:The title compound, C18H14Cl2N2O2, crystallizes with two mol-ecules, A and B, in the asymmetric unit. In mol-ecule A, the dihedral angles between the central pyrazole ring and pendant di-chloro-benzene and p-tolyl rings are 2.18?(16) and 46.78?(16)°, respectively. In mol-ecule B, the equivalent angles are 27.45?(16) and 40.45?(18)°, respectively. Each mol-ecule features an intra-molecular O-H?O hydrogen bond, which closes an S(6) ring and mol-ecule A also features a C-H?O inter-action. In the crystal, weak C-H?? interactions and aromatic ?-? stacking [shortest centroid-centroid separation = 3.707?(2)?Å] generate a three-dimensional network.

| S-EPMC4257223 | biostudies-literature

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