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1.  1,3-Bis(2-chloro­phen­yl)thio­urea: a monoclinic polymorph 
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.
doi:10.1107/S1600536811041894
PMCID: PMC3247371  PMID: 22219989
2.  N-(4-Chloro­phen­yl)-2-methyl­benzamide 
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.
doi:10.1107/S1600536809002633
PMCID: PMC2968167  PMID: 21581984
3.  2-Chloro-N-(3-chloro­phen­yl)benzamide 
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.
doi:10.1107/S1600536808018102
PMCID: PMC2961659  PMID: 21202929
4.  N-(4-Chloro­phen­yl)benzamide 
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.
doi:10.1107/S1600536808008155
PMCID: PMC2961007  PMID: 21202156
5.  2-Methyl-N-p-tolyl­benzamide: a second monoclinic polymorph 
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.
doi:10.1107/S1600536810010378
PMCID: PMC2983768  PMID: 21580722
6.  2-Chloro-N-(4-meth­oxy­phen­yl)benzamide 
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.
doi:10.1107/S1600536810043035
PMCID: PMC3009019  PMID: 21589131
7.  N-(4-Chloro­phen­yl)-3-methyl­benzamide 
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
doi:10.1107/S1600536809041956
PMCID: PMC2971070  PMID: 21578371
8.  Crystal structure of 8-hy­droxy­quinoline: a new monoclinic polymorph 
In an attempt to grow 8-hy­droxy­quinoline–acetamino­phen co-crystals from equimolar amounts of conformers in a chloro­form–ethanol solvent mixture at room temperature, the title compound, C9H7NO, was obtained. The mol­ecule is planar, with the hy­droxy H atom forming an intra­molecular O—H⋯N hydrogen bond. In the crystal, mol­ecules form centrosymmetric dimers via two O—H⋯N hydrogen bonds. Thus, the hy­droxy H atoms are involved in bifurcated O—H⋯N hydrogen bonds, leading to the formation of a central planar four-membered N2H2 ring. The dimers are bound by inter­molecular π–π stacking [the shortest C⋯C distance is 3.2997 (17) Å] and C—H⋯π inter­actions into a three-dimensional framework. The crystal grown represents a new monoclinic polymorph in the space group P21/n. The mol­ecular structure of the present monoclinic polymorph is very similar to that of the ortho­rhom­bic polymorph (space group Fdd2) studied previously [Roychowdhury et al. (1978 ▶). Acta Cryst. B34, 1047–1048; Banerjee & Saha (1986 ▶). Acta Cryst. C42, 1408–1411]. The structures of the two polymorphs are distinguished by the different geometries of the hydrogen-bonded dimers, which in the crystal of the ortho­rhom­bic polymorph possess twofold axis symmetry, with the central N2H2 ring adopting a butterfly conformation.
doi:10.1107/S1600536814016110
PMCID: PMC4186174  PMID: 25309256
8-hy­droxy­quinoline; hydrogen bonds; polymorphism; crystal structure
9.  A monoclinic polymorph of 1-(4-chloro­phen­yl)-3-(4-methoxy­phen­yl)prop-2-en-1-one 
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.
doi:10.1107/S1600536809054956
PMCID: PMC2979778  PMID: 21579708
10.  N-(2-Chloro­phen­yl)-2-methyl­benzamide 
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.
doi:10.1107/S1600536808020229
PMCID: PMC2962055  PMID: 21203140
11.  3-Chloro-N-(3-chloro­phen­yl)benzamide 
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.
doi:10.1107/S1600536808012099
PMCID: PMC2961234  PMID: 21202429
12.  N-(3-Chloro­phen­yl)-2-methyl­benzamide 
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.
doi:10.1107/S1600536808010143
PMCID: PMC2961145  PMID: 21202348
13.  N-(3-Chloro­phen­yl)-4-methyl­benzamide hemihydrate 
In the title compound, C14H12ClNO·0.5H2O, the water mol­ecule is located on a twofold axis of symmetry. The meta-Cl atom in the aniline ring is positioned anti to the N—H bond. The two benzene rings make a dihedral angle of 40.40 (11)°. The crystal structure is stabilized by inter­molecular N—H⋯O and O—H⋯O hydrogen bonds, which link the mol­ecules into chains along the a axis.
doi:10.1107/S1600536811040992
PMCID: PMC3247315  PMID: 22219933
14.  3-Chloro-N-(2-chloro­phen­yl)benzamide 
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.
doi:10.1107/S1600536811051944
PMCID: PMC3254408  PMID: 22259551
15.  2-Chloro-N-(3,4-dimethyl­phen­yl)benzamide 
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.
doi:10.1107/S1600536811027267
PMCID: PMC3213471  PMID: 22091050
16.  2-Chloro-N-(2,3-dimethyl­phen­yl)benzamide 
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].
doi:10.1107/S1600536810024943
PMCID: PMC3007441  PMID: 21588231
17.  4-Chloro-N-(2,6-dichloro­phen­yl)benzamide 
The title compound, C13H8Cl3NO, crystallizes with four mol­ecules in the asymmetric unit. In the mol­ecular structure, the conformations of the central amide –CONH group show a wide range of dihedral angles with respect to the attached aromatic rings (benzoyl and anilino). The dihedral angles between the amide group and the benzoyl ring are 8.1 (3), 4.3 (3), 27.8 (1) and 32.7 (2)° in the four mol­ecules. The amide group is twisted out of the plane of the anilino ring, as shown by the dihedral angles of 85.4 (1), 74.3 (1), 88.1 (1) and 77.6 (1)° in the four mol­ecules. The aromatic rings are oriented at dihedral angles of 86.6 (1), 78.0 (1), 60.3 (1) and 69.8 (1)° in the four mol­ecules. The crystal structure is stabilized via inter­molecular N—H⋯O hydrogen bonds, aromatic aromatic inter­actions, short Cl⋯Cl contacts and C—H⋯Cl hydrogen bonds. Inter­molecular hydrogen bonds connect the mol­ecules into two distinct chains running along the c axis of the crystal. One mol­ecule forms an inversion dimer in which the main inter­actions are π–π stacking [centroid–centroid distances = 3.749 (1) and 3.760 (1) Å] and a short Cl⋯Cl contact of 3.408 (1) Å.
doi:10.1107/S160053680902265X
PMCID: PMC2969447  PMID: 21582902
18.  N-(3-Chloro­phen­yl)benzamide 
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.
doi:10.1107/S1600536808001311
PMCID: PMC2960316  PMID: 21201488
19.  4-Chloro-N-(3-chloro­phen­yl)benzamide 
The title compound, C13H9Cl2N, has an intra­molecular C—H⋯O close contact, and presents the NH group syn to the meta-chloro group in the aniline ring and trans to the C=O group. The crystal packing is formed by infinite chains of N—H⋯O hydrogen bonds along the c axis. Cl⋯Cl [3.474 (1) Å] contacts link chains. The crystal used for data collection was a twin, the domains related by the twin law 0.948 (1)/0.052 (1).
doi:10.1107/S1600536809034308
PMCID: PMC2970278  PMID: 21577890
20.  N-(4-Chloro­phen­yl)-3,4,5-trimethoxy­benzamide 
In the title compound, C16H16ClNO4, the dihedral angle between the two aromatic rings is 67.33 (8)°. The crystal packing shows strong inter­molecular N—H⋯O hydrogen bonds that link the mol­ecules to form chains along [01].
doi:10.1107/S1600536808023234
PMCID: PMC2962079  PMID: 21203315
21.  2-Chloro-N-(3-methyl­phen­yl)benzamide 
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.
doi:10.1107/S1600536812005739
PMCID: PMC3295494  PMID: 22412605
22.  An ortho­rhom­bic polymorph of 5-[(4-methyl­phen­yl)diazen­yl]salicylaldehyde 
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.
doi:10.1107/S1600536809046868
PMCID: PMC2971774  PMID: 21578791
23.  4-Chloro-N-(3,5-dimethyl­phen­yl)benzamide 
In the mol­ecular structure of the title compound, C15H14ClNO, the amide group forms dihedral angles of 15.8 (2) and 27.2 (2)°, respectively, with the benzoyl and aniline rings, while the angle between the benzoyl and aniline rings is 11.5 (1)°. The crystal structure is stabilized by N—H⋯O hydrogen bonds, which give rise to infinite chains running along the c axis.
doi:10.1107/S1600536812007180
PMCID: PMC3297881  PMID: 22412684
24.  N-[(2-Chloro­phen­yl)sulfon­yl]-2-meth­oxy­benzamide 
The title compound, C14H12ClNO4S, crystallizes with two mol­ecules in the asymmetric unit. The dihedral angles between the benzene rings are 89.68 (1) (mol­ecule 1) and 82.9 (1)° (mol­ecule 2). In each mol­ecule, intra­molecular N—H⋯O hydrogen bonds between the amide H atom and the meth­oxy O atom generate S(6) loops. In the crystal, mol­ecule 2 is linked into inversion dimers through pairs of C—H⋯O inter­actions, forming an R 2 2(8) ring motif. Mol­ecules 1 and 2 are further linked along the b-axis direction through C—H⋯π inter­actions. The crystal structure is further stabilized by several π–π stacking inter­actions [centroid–centroid separations = 3.7793 (1), 3.6697 (1) and 3.6958 (1) Å], thus generating a three-dimensional architecture.
doi:10.1107/S1600536813029012
PMCID: PMC3884364  PMID: 24454140
25.  2-Chloro-N-(4-methyl­phen­yl)benzamide 
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.
doi:10.1107/S1600536811041651
PMCID: PMC3247352  PMID: 22219970

Results 1-25 (356516)