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The title compound, C13H10Cl2N2S, represents a monoclinic polymorph of the previously reported ortho­rhom­bic form [Ramnathan et al. (1996 ▶). Acta Cryst. C52, 134–136]. The mol­ecule is twisted with the dihedral angle between the benzene rings being 55.37 (7)°. The N—H atoms are syn to each other, which contrasts their anti disposition in the ortho­rhom­bic form. In the crystal, mol­ecules assemble into zigzag chains along the c axis via N—H⋯S hydrogen bonds. Chains are connected into layers via C—H⋯Cl inter­actions, and these stack along the a axis.

The crystal structure of the title compound, C16H13ClO2 (II), (space group P21/c,) is a polymorph of the structure, (I), reported by Harrison, Yathirajan, Sarojini, Narayana & Indira [Acta Cryst. (2006), E62, o1647–o1649] in the ortho­rhom­bic space group Pna21. The dihedral angle between the mean planes of the 4-chloro- and 4-meth­oxy-substituted benzene rings is 52.9 (1)° in (II) compared to 21.82 (6)° for polymorph (I). The dihedral angles between the mean planes of the prop-2-en-1-one group and those of the 4-chloro­phenyl and 4-methoxy­phenyl rings are 23.3 (3) and 33.7 (1)°, respectively. in (II). The corresponding values are 17.7 (1) and 6.0 (3)°, respectively, in polymorph (I). In the crystal, weak C—H⋯π inter­actions are observed.

In the structure of the title compound (N2CP2MBA), C14H12ClNO, the conformations of the N—H and C=O bonds are trans to each other. Furthermore, the conformation of the N—H bond is syn to the ortho-chloro group in the aniline ring and the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring, similar to what is observed in 2-chloro-N-(2-chloro­phen­yl)benzamide and 2-methyl-N-phenyl­benzamide. The amide group makes almost the same dihedral angles of 41.2 (14) and 42.2 (13)° with the aniline and benzoyl rings, respectively, while the dihedral angle between the benzoyl and aniline rings is only 7.4 (3)°. The mol­ecules in N2CP2MBA are packed into chains through N—H⋯O hydrogen bonds.

The conformation of the N—H bond in the structure of the title compound, C14H12ClNO, is anti to the meta-chloro substituent in the aniline ring, while the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring. The conformations of the N—H and C=O bonds are anti to each other, similar to those observed in 2-methyl-N-(3-methyl­phen­yl)benzamide (N3MP2MBA). The –NHC(=O)– group makes a dihedral angle of 55.8 (7)° with the benzoyl ring, while the angle between the benzoyl and aniline rings is 37.5 (1)°; the respective values for N3MP2MBA are 55.2 (7) and 36.2 (1)°. N—H⋯O hydrogen bonds link the mol­ecules into infinite chains running along the c axis.

In the structure of the title compound, C14H12ClNO, the N—H and C=O bonds are trans to each other. Furthermore, the C=O bond is syn to the ortho-methyl group in the benzoyl ring, similar to what is observed in 2-methyl-N-(4-methyl­phen­yl)benzamide and 2-methyl-N-phenyl­benzamide. The amide linkage (–NHCO–) makes dihedral angles of 36.9 (7) and 46.4 (5)° with the aniline and benzoyl rings, respectively, while the dihedral angle between the benzoyl and aniline rings is 83.1 (1)°. In the crystal structure, mol­ecules form chains running along the b axis through N—H⋯O hydrogen bonds.

The title compound, C15H15NO, (I), is a polymorph of the structure (II) reported by Gowda et al. [Acta Cryst. (2008), E64, o1494]. Compound (II) crystalllizes in the space group C2/c (Z = 8), whereas the title compound occurs in space group P21/c (Z = 4). The two mol­ecular structures differ slightly in the relative orientations of their central amide group with respect to the benzoyl ring [dihedral angles of 55.99 (7) for (I) and 59.96 (11)° for (II)] and in the inclination of the benzoyl and aniline rings [88.67 (8) for (I) and 81.44 (5)° for (II)]. In the crystal structure of (I), mol­ecules are linked by N—H⋯O hydrogen bonds, forming C(4) chains, which are augmented by weak C—H⋯O inter­actions. The structure is further stabilized by C—H⋯π contacts involving both of the aromatic rings.

In the structure of the the title compound, C13H9Cl2NO, the N—H and C=O groups are mutually trans. Furthermore, the conformation of the C=O group is syn to the ortho-chloro group in the benzoyl ring, while the N—H bond is anti to the meta-chloro group in the aniline ring. The amide group forms dihedral angles of 89.11 (19) and 22.58 (37)°, respectively, with the benzoyl and aniline rings, while the benzoyl and aniline rings form a dihedral angle of 69.74 (14)°. The mol­ecules are linked into infinite chains through inter­molecular N—H⋯O hydrogen bonds.

The title compound, C14H12N2O2, is an ortho­rhom­bic polymorph of the previously reported monoclinic form [Bakir et al. (2005 ▶). Acta Cryst. E61, o1611–o1613]. The dihedral angle between the aromatic rings is 4.32 (13)°. The mol­ecular structures of the two polymorphs, including short intra­molecular O—H⋯O hydrogen bonds between the the hydr­oxy and keto groups, are quite similar but their crystal packings are distinct. Unlike the monoclinic form, in which centrosymmetrically related hydr­oxy and keto groups form {⋯H⋯O}2 synthons via weak O—H⋯O contacts, leading to dimeric aggregates, in the ortho­rhom­bic form, the hydrogen bonding between these groups leads to the formation of supra­molecular chains orientated along the a axis.

In the title compound, C13H9Cl2NO, the meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-Cl atom in the aniline ring is positioned syn to the N—H bond. The two aromatic rings are almost coplanar, making a dihedral angle of 4.73 (5)°. The crystal structure is stabilized by N—H⋯O hydrogen bonds, which link the mol­ecules into chains along the b axis.

The structure of the title compound, C13H10ClNO, resembles those of N-phen­ylbenzamide, N-(2-chloro­phenyl)­benzamide and other benzanilides, with similar bond parameters. The amide group –NHCO– makes a dihedral angle of 29.95 (9)° with the benzoyl ring, while the benzoyl and aniline rings form a dihedral angle of 60.76 (3)°. The structure shows both intra- and inter­molecular hydrogen bonding. The mol­ecules are linked by N—H⋯O hydrogen bonds into chains running along the [100] direction.

The conformation of the N—H bond in the structure of the title compound (N3CPBA), C13H10ClNO, is anti to the meta chloro substituent in the aniline benzene ring, similar to that observed with respect to the ortho chloro substituent in N-(2-chloro­phen­yl)benzamide (N2CPBA) and meta chloro substituent in N-(3,4-dichloro­phen­yl)benzamide (N34DCPBA), but in contrast to the syn conformation observed with respect to both the ortho and the meta chloro substituents in N-(2,3-dichloro­phen­yl)benzamide (N23DCPBA). The bond parameters in N3CPBA are similar to those in N-phenyl­benzamide, N2CPBA, N23DCPBA, N34DCPBA and other benzanilides. The amide group –NHCO– makes a dihedral angle of 18.2 (2)° with the benzoyl ring, while the dihedral angle between the two benzene rings is 61.0 (1)°. The mol­ecules are linked into chains along the b axis by N—H⋯O hydrogen bonds.

The asymmetric unit in the title compound, C5H5NO, comprises two independent but virtually identical mol­ecules of 2-pyridone, and represents a monoclinic polymorph of the previously reported ortho­rhom­bic (P212121) form [Penfold (1953 ▶). Acta Cryst. 6, 591–600; Ohms et al. (1984 ▶). Z. Kristallogr. 169, 185–200; Yang & Craven (1998 ▶). Acta Cryst. B54, 912–920]. The independent mol­ecules are linked into supra­molecular dimers via eight-membered {⋯HNC(O)}2 amide synthons in contrast to the helical supra­molecular chains, mediated by {⋯HNC(O)} links, found in the ortho­rhom­bic form.

In the crystal structure of the title compound, C13H9Cl2NO, the N—H and C=O bonds are anti to each other in the two independent mol­ecules. In one mol­ecule, the N—H bond is syn to the meta-chloro group of the attached ring; it is anti in the other mol­ecule. This relationship is also observed between the C=O bond and the meta-chloro substituent of its attached ring. The amide –NHCO– group makes dihedral angles of 31.5 (4) and 34.7 (3)° with the aniline rings; it makes dihedral angles of 37.4 (3) and 37.2 (3)° with the benzoyl rings. The two rings are nearly coplanar, with dihedral angles of 9.1 (2) and 7.3 (3)° in the two independent mol­ecules. Adjacent mol­ecules are linked into infinite chains through N—H⋯O hydrogen bonds.

In the title compound, C14H12ClNO2, the chloro- and meth­oxy-substituted benzene rings are close to orthogonal [dihedral angle = 79.20 (3)°]. These rings also make angles of 45.9 (3) and 33.5 (3)° with the amide –CONH– unit. The meth­oxy substituent lies close to the meth­oxy­benzene ring plane, with a maximum deviation of 0.142 (3) Å for the methyl C atom. The N—H bond is anti to the 2-chloro substituent of the aniline ring. In the crystal structure, inter­molecular N—H⋯O hydrogen bonds form C(4) chains augmented by a weak C—H⋯O inter­action involving an ortho H atom of the meth­oxy benzene ring that generates an R 2 1(6) motif. The chains stack the mol­ecules into columns down the b axis. Adjacent columns are linked by additional C—H⋯O and C—H⋯π contacts, generating a three-dimensional network.

In the structure of the title compound, C14H12ClNO, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond, while the meta-methyl group in the aniline ring is positioned anti to the N—H bond. The amide group forms dihedral angles of 60.1 (1) and 22.0 (1)°, respectively, with the benzoyl and aniline rings, while the angle between these rings is 38.7 (1)°. The crystal structure is stabilized by N—H⋯O hydrogen bonds, which give rise to infinite chains running along the c axis.

Recently, we reported the first monoclinic [Kuai & Cheng (2011). Acta Cryst., E67, o2787] and the ortho­rhom­bic polymorph [Kuai & Cheng (2011). Acta Cryst., E67, o3014] of the title compound, C15H12N2O2. Another monoclinic polymorph was obtained accidentally by the hydro­thermal reaction of the title compound with manganese chloride in the presence of potassium hydroxide at 413 K. The asymmetric unit consists of four independent mol­ecules. In the crystal, O—H⋯N hydrogen bonds link the independent mol­ecules into four separate chains parallel to the b axis.

The title compound, C14H12N2, in contrast to the previously reported monoclinic polymorph [Lei et al. (2009 ▶). Acta Cryst. E65, o2613], crystallizes in the ortho­rhom­bic crystal system. The dihedral angle between the imidazole ring system and the phenyl ring is 76.78 (16)°. Weak C—H⋯N and C—H⋯π inter­actions are observed in the crystal structure.

The title compound, C20H20Br2N2O2, a tetra­dentate Schiff base, is the enanti­omerically pure R,R-diastereomer of four possible stereoisomers. The mol­ecular structure reveals two strong intra­molecular O—H⋯N hydrogen bonds between the hy­droxy O atom and the imino N atom, which each generate S(6) rings. In the crystal, mol­ecules are stacked in columns along the a axis; when viewed down the b axis, successive columns are stacked in the opposite direction. The structure reported herein is the monoclinic polymorph of the previously reported ortho­rhom­bic form [Yi & Hu (2009 ▶). Acta Cryst. E65, o2643], in which the complete mol­ecule is generated by a crystallographic twofold axis.

In the title compound, C15H14ClNO, the ortho- and meta-methyl substituents in the aniline ring are anti to the N—H bond. The dihedral angle between the benzoyl and aniline benzene rings is 95.0 (1)°. N—H⋯O hydrogen bonds and C—H⋯π inter­actions link the mol­ecules in the crystal structure.

In the structure of the the title compound, C15H14ClNO, the N—H and C=O bonds are trans to each other and the amide O atom is anti to the ortho-Cl atom in the benzoyl ring. The amide group makes dihedral angles of 61.2 (6) and 42.2 (8)° with the benzoyl and aniline rings, respectively. In the crystal, the mol­ecules are linked into infinite chains by N—H⋯O hydrogen bonds.

In the title compound, C14H12ClNO, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond. The benzoyl and aniline benzene rings are tilted relative to each other by 82.8 (1)°. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into infinite chains running along the c-axis direction.

In the structure of the title compound, C14H12ClNO, the conformations of the N—H and C=O bonds are anti to each other. Furthermore, the conformation of the C=O bond is syn to the meta-methyl group in the benzoyl ring. The central –NH—C(=O)– amido group makes a dihedral angle of 32.4 (1)° with the benzoyl ring and 36.1 (1)° with the anilino ring. The dihedral angle between the two benzene rings is 68.4 (1)°. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into chains running along the a axis

In the title compound, C15H14ClNO, the conformation of the N—H bond is anti to the meta-methyl group in the aniline ring, while that of the C=O bond is anti to the ortho-chloro group in the benzoyl ring. The mean planes through the two benzene rings make a dihedral angle of 80.8 (2)°. In the crystal, mol­ecules are linked by inter­molecular N—H⋯O hydrogen bonds, forming column-like chains along the b axis.

In the mol­ecular structure of the title compound, C14H12ClNO, the meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-methyl group in the aniline ring is positioned syn to the N—H bond. The two benzene rings are nearly coplanar [dihedral angle = 3.48 (5)°]. The crystal structure is stabilized by N—H⋯O hydrogen bonds, which link the mol­ecules into chains along the b axis.

In the title compound, C15H14ClNO, the N—H and C=O bonds in the amide group are anti to each other. The amide group is inclined at 60.3 (1)° to the chloro-substituted benzoyl ring and at 59.2 (1)° to the dimethyl-substituted aniline ring. The mean planes through the two benzene rings make a dihedral angle of 7.7 (1)°. In the crystal structure, mol­ecules are linked by inter­molecular N—H⋯O hydrogen bonds, forming chains along [010].