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A monoclinic polymorph of N-(3-chloro-phen-yl)benzamide.

ABSTRACT: The title compound, C(13)H(10)ClNO, (I), is a polymorph of the structure, (II), first reported by Gowda et al. [Acta Cryst. (2008), E64, o462]. In the original report, the compound crystallized in the ortho-rhom-bic space group Pbca (Z = 8), whereas the structure reported here is monoclinic P21/c (Z = 4). The principal difference between the two forms lies in the relative orientations of the phenyl and benzene rings [dihedral angle = 8.90 (13)° for (I) and 61.0 (1)° for (II)]. The inclination of the amide -CONH- units to the benzoyl ring is more similar [15.8 (7)° for (I) and 18.2 (2)° for (II)]. In both forms, the N-H bonds are anti to the 3-chloro substituents of the aniline rings. In the crystal, inter-molecular N-H⋯O hydrogen bonds form C(4) chains along c. These chains are bolstered by weak C-H⋯O inter-actions that generate R(2) (1)(6) and R(2) (1)(7) ring motifs.

SUBMITTER: Saeed A

PROVIDER: S-EPMC3008970 | biostudies-literature |

REPOSITORIES: biostudies-literature

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A monoclinic polymorph of 1-(4-chloro-phen-yl)-3-(4-methoxy-phen-yl)prop-2-en-1-one.

Project description:The crystal structure of the title compound, C(16)H(13)ClO(2) (II), (space group P2(1)/c,) is a polymorph of the structure, (I), reported by Harrison, Yathirajan, Sarojini, Narayana & Indira [Acta Cryst. (2006), E62, o1647-o1649] in the ortho-rhom-bic space group Pna2(1). The dihedral angle between the mean planes of the 4-chloro- and 4-meth-oxy-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-chloro-phenyl and 4-methoxy-phenyl 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?? inter-actions are observed.

| S-EPMC2979778 | biostudies-literature

N-(3-Chloro-phen-yl)benzamide.

Project description:The conformation of the N-H bond in the structure of the title compound (N3CPBA), C(13)H(10)ClNO, 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-chloro-phen-yl)benzamide (N2CPBA) and meta chloro substituent in N-(3,4-dichloro-phen-yl)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-dichloro-phen-yl)benzamide (N23DCPBA). The bond parameters in N3CPBA are similar to those in N-phenyl-benzamide, 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 mol-ecules are linked into chains along the b axis by N-H⋯O hydrogen bonds.

| S-EPMC2960316 | biostudies-literature

1,3-Bis(2-chloro-phen-yl)thio-urea: a monoclinic polymorph.

Project description:The title compound, C(13)H(10)Cl(2)N(2)S, represents a monoclinic polymorph of the previously reported ortho-rhom-bic form [Ramnathan et al. (1996 ?). Acta Cryst. C52, 134-136]. The mol-ecule 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 ortho-rhom-bic form. In the crystal, mol-ecules assemble into zigzag chains along the c axis via N-H?S hydrogen bonds. Chains are connected into layers via C-H?Cl inter-actions, and these stack along the a axis.

| S-EPMC3247371 | biostudies-other

3-Chloro-N-(3-chloro-phen-yl)benzamide.

Project description:In the crystal structure of the title compound, C(13)H(9)Cl(2)NO, the N-H and C=O bonds are anti to each other in the two independent mol-ecules. In one mol-ecule, the N-H bond is syn to the meta-chloro group of the attached ring; it is anti in the other mol-ecule. 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 mol-ecules. Adjacent mol-ecules are linked into infinite chains through N-H?O hydrogen bonds.

| S-EPMC2961234 | biostudies-literature

4-Chloro-N-(2-chloro-phen-yl)benzamide.

Project description:In the mol-ecular structure of the title compound, C(13)H(9)Cl(2)NO, the amide N-C=O plane makes dihedral angles of 31.53?(8) and 36.23?(8)°, respectively, with the 4-chloro- and 2-chloro-phenyl rings. The dihedral angle between the two benzene rings is 6.25?(8)°. The mol-ecules are stacked in columns along the b axis through inter-molecular N-H?O hydrogen bonds. The columns are further connected by weak C-H?O hydrogen bonds. The compound is not isomorphous with the fluoro analogue.

| S-EPMC2959385 | biostudies-literature

3-Chloro-N-(2-chloro-phen-yl)benzamide.

Project description:In the title compound, C(13)H(9)Cl(2)NO, 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 mol-ecules into chains along the b axis.

| S-EPMC3254408 | biostudies-literature

2-Chloro-N-(3-chloro-phen-yl)benzamide.

Project description:In the structure of the the title compound, C(13)H(9)Cl(2)NO, 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 mol-ecules are linked into infinite chains through inter-molecular N-H?O hydrogen bonds.

| S-EPMC2961659 | biostudies-literature

2-Chloro-N-(2,6-dichloro-phen-yl)benzamide.

Project description:In the structure of the title compound (N26DCP2CBA), C(13)H(8)Cl(3)NO, the conformations of N-H and C=O bonds in the amide group are trans to each other, similar to that observed in N-(2,6-dichloro-phen-yl)benzamide, 2-chloro-N-phenyl-benzamide, 2-chloro-N-(2-chloro-phen-yl)benzamide and 2-chloro-N-(2,3-dichloro-phen-yl)benzamide with similar bond parameters. Furthermore, the position of the amide O atom is syn to the ortho-chloro group in the benzoyl ring. The amide group makes a dihedral angle of 59.8?(1)° with the benzoyl ring, while the benzoyl and aniline rings make a dihedral angle of 8.1?(2)°. The mol-ecules are linked by N-H?O hydrogen bonds into infinite chains running along the b axis.

| S-EPMC2962123 | biostudies-literature

N-(3-Chloro-phen-yl)-2-methyl-benzamide.

Project description:The conformation of the N-H bond in the structure of the title compound, C(14)H(12)ClNO, 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-methyl-phen-yl)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 mol-ecules into infinite chains running along the c axis.

| S-EPMC2961145 | biostudies-literature

N-(4-Chloro-phen-yl)-2-methyl-benzamide.

Project description:In the structure of the title compound, C(14)H(12)ClNO, 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-methyl-phen-yl)benzamide and 2-methyl-N-phenyl-benzamide. 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, mol-ecules form chains running along the b axis through N-H?O hydrogen bonds.

| S-EPMC2968167 | biostudies-literature

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