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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.  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
3.  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
4.  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
5.  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
6.  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
7.  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
8.  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
9.  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
10.  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
11.  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
12.  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
13.  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
14.  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
15.  A third polymorph of 1,4-bis­(1H-benzimid­azol-2-yl)benzene 
The title compound, C20H14N4, is a new polymorph of the previously reported structures, which were ortho­rhom­bic, space group Pbca [Bei et al. (2000). Acta Cryst. C56, 718–719] and monoclinic, space group P21/c [Dudd et al. (2003). Green Chem. 5, 187–192]. The asymmetric unit consists of two independent mol­ecules in which the dihedral angels between the central benzene ring and the outer benzimidazole ring systems are 16.81 (10) and 14.23 (10)° in one molecule and 26.09 (10) and 37.29 (10)° in the other. In the crystal, mol­ecules are linked by N—H⋯N and C—H⋯N hydrogen bonds into a tape running along the c-axis direction.
doi:10.1107/S1600536814011179
PMCID: PMC4051014  PMID: 24940273
16.  3-Chloro-N-(3-methyl­phen­yl)benzamide 
In the mol­ecular structure of the title compound, C14H12ClNO, the meta-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 two aromatic rings make a dihedral angle of 77.4 (1)°. In the crystal, the molecules are linked by N—H⋯O hydrogen bonds, forming C(4) chains propagating in [010].
doi:10.1107/S1600536811047271
PMCID: PMC3238934  PMID: 22199783
17.  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
18.  4-Chloro-N-(2,3-dimethyl­phen­yl)benzamide 
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.
doi:10.1107/S1600536811053256
PMCID: PMC3254536  PMID: 22259483
19.  4-Chloro-N-(2,6-dimethyl­phen­yl)benzamide 
The conformations of the N—H and C=O bonds in the structure of the title compound (N26DMP4CBA), C15H14ClNO, are anti to each other, similar to that observed in N-phenyl­benzamide, N-(3,4-dimethyl­phen­yl)benzamide, N-(2,6-dichloro­phen­yl)benzamide and other benzanilides. There are three mol­ecules in the asymmetric unit of N26DMP4CBA. The central amide group is tilted with respect to the benzoyl ring by 45.2 (1)° in mol­ecule 1, 21.2 (2)° in mol­ecule 2 and 14.9 (2)° in mol­ecule 3. The dihedral angles between the benzoyl and aniline rings are 39.9 (1), 51.0 (1) and 86.3 (3)° in mol­ecules 1, 2 and 3, respectively. Inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into infinite chains running along the [101] direction. One xylyl group is disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.
doi:10.1107/S1600536808019120
PMCID: PMC2961789  PMID: 21202983
20.  2-Chloro-N-(3,5-dimethyl­phen­yl)benzamide 
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.
doi:10.1107/S1600536809001706
PMCID: PMC2968629  PMID: 21582117
21.  3-Chloro-N-(2-methyl­phen­yl)benzamide 
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.
doi:10.1107/S1600536811048756
PMCID: PMC3239024  PMID: 22199872
22.  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
23.  Crystal structure of 5-amino-5′-chloro-6-(4-chloro­benzo­yl)-8-nitro-2,3-di­hydro-1H-spiro­[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one including an unknown solvent mol­ecule 
The asymmetric unit of the title compound, C21H15Cl2N5O4, contains two independent mol­ecules (A and B) having similar conformations. The amine (NH2) group forms an intra­molecular hydrogen bond with the benzoyl group, giving an S(6) ring motif in both mol­ecules. The central six-membered rings adopt sofa conformations and the imidazole rings are planar (r.m.s deviations = 0.0150 and 0.0166 Å). The pyridine and imidazole rings are inclined to one another by 3.54 (1) and 3.03 (1)° in mol­ecules A and B, respectively. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, forming chains along the a axis which enclose R 2 2(16) ring motifs. The rings are linked by weak N—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π inter­actions forming sheets lying parallel to (001). A region of disordered electron density, most probably disordered solvent mol­ecules, occupying voids of ca 753 Å3 for an electron count of 260, was treated using the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155]. Their formula mass and unit-cell characteristics were not taken into account during refinement.
doi:10.1107/S1600536814017486
PMCID: PMC4186207  PMID: 25309286
crystal structure; spiro; imidazole; pyridine-indoline C—H⋯π inter­actions; hydrogen bonding
24.  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
25.  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

Results 1-25 (638612)