Chloro-substituted Benzene Rings Research Articles

Crystal structure and Hirshfeld surface analysis of 1-(4-chloro-phen-yl)-2-{[5-(4-chloro-phen-yl)-1,3,4-oxa-diazol-2-yl]sulfan-yl}ethanone.

In the title compound, C16H10Cl2N2O2S, the dihedral angles formed by the chloro-substituted benzene rings with the central oxa-diazole ring are 6.54 (9) and 6.94 (8)°. In the crystal, C-H⋯N hydrogen bonding links the mol-ecules into undulating ribbons running parallel to the b axis. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are the H⋯C (18%), H⋯H (17%), H⋯Cl (16.6%), H⋯O (10.4%), H⋯N (8.9%) and H⋯S (5.9%) inter-actions.

3-(4-Chlorophenyl)-5-[4-(methylsulfanyl)phenyl]-1H-pyrazole

In the title compound, C16H13ClN2S, the pyrazole ring is almost planar with an r.m.s. deviation of 0.0457 Å which forms dihedral angles of 2.875 (4) and 84.83 (7)° with the chloro-substituted benzene ring and the methylsulfanyl-substituted ring, respectively. In the crystal, N—H...N and C—H...Cl hydrogen bonds contribute to the formation of a three-dimensional network. In addition, several offset π–π stacking interactions are also present.

2-({5-[(4-Chlorophenoxy)methyl]-4-phenyl-4H-1,2,4-triazol-3-yl}sulfanyl)-N-phenylacetamide

The title molecule, C23H19ClN4O2S, is in an `extended' conformation. In the crystal, pairwise N—H...N and C—H...O hydrogen bonds lead to the formation of `stair-step' chains. C—H...π interactions further contribute to the consolidation of the molecular packing. The 4-chlorophenyl group is disordered over two sets of sites in a 0.948 (2):0.052 (2) ratio. The dihedral angle between the two components of the disordered chloro-substituted benzene ring is 15.76 (9) °.

Crystal structure of 2-(4-chloro-benzamido)-benzoic acid.

In the title mol­ecule, C14H10ClNO3, the amide C=O bond is anti to the o-carb­oxy substituent in the adjacent benzene ring, a conformation that facilitates the formation of an intra­molecular amide-N—H⋯O(carbon­yl) hydrogen bond that closes an S(6) loop. The central amide segment is twisted away from the carb­oxy- and chloro-substituted benzene rings by 13.93 (17) and 15.26 (15)°, respectively. The most prominent supra­molecular inter­actions in the crystal packing are carb­oxy­lic acid-H⋯O(carbox­yl) hydrogen bonds that lead to centrosymmetric dimeric aggregates connected by eight-membered {⋯HOC=O}2 synthons.

Ethyl 6-(4-chlorophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate

The asymmetric unit of the title compound, C21H18ClFO3, contains two independent mol­ecules. In one mol­ecule (A), the 4-chloro­phenyl, oxo­cyclo­hex-3-ene, carboxyl­ate, and ethyl groups were refined as disordered over two sets of sites with a 0.684 (5):0.316 (5) ratio. The cyclo­hexene ring in the disordered mol­ecule is in a slightly distorted envelope conformation for the major component (with the C atom bound to the carboxylate group being the flap atom) and in a screw-boat conformation for the minor component. In the ordered mol­ecule (B), the cyclo­hexene ring is in a half-chair conformation. The dihedral angles between the mean planes of the fluoro- and chloro-substituted benzene rings are 89.9 (7) (only the major component is considered for A) and 76.4 (7)° (B). In the crystal, inversion dimers are observed along with weak C—H⋯O hydrogen bonds, which form chains along [100].

2-(4-Chlorophenyl)-4-phenyl-1,2-dihydroquinazoline

In the title compound, C20H15ClN2, the pyrimidine ring is in a flattened half-chair conformation. The phenyl and chloro-substituted benzene rings form dihedral angles of 84.97 (5) and 80.23 (4)°, respectively, with the benzene ring of the di­hydro­quinazoline group. The dihedral angle between the phenyl and chloro-substituted benzene rings is 61.71 (5)°. In the crystal, mol­ecules are arranged in inter­secting layers parallel to (101) and (-102), with N—H⋯N hydrogen bonds linking mol­ecules along [010]. In addition, a weak C—H⋯π inter­action is observed.

3-(4-Bromo-phen-yl)-1-butyl-5-[1-(2-chloro-6-methyl-phen-yl)-1H-tetra-zol-5-yl]imidazolidine-2,4-dione.

In the title mol­ecule, C21H20BrClN6O2, the chloro-substituted benzene ring forms a dihedral angle of 77.84 (7)° with the tetra­zole ring and the bromo-substituted ring forms a dihedral angle of 43.95 (6)° with the imidazole ring. The dihedral angle between the tetra­zole and imidazole rings is 67.42 (8)°. The terminal methyl group of the butyl substituent is disordered over two sets of sites, with refined occupancies 0.67 (3) and 0.33 (3). In the crystal, there is a short Br⋯N contact of 3.183 (2) Å.

2,4,6-Trinitrophenyl 3-chlorobenzoate

In the title benzoate derivative, C13H6ClN3O8, the planes of the benzene rings form a dihedral angle of 73.59 (7)°. The central ester unit forms an angle of 20.38 (12)° with the chloro-substituted benzene ring. In the crystal, mol­ecules are linked by weak C—H⋯O inter­actions, forming helical chains along [101] and [100].

2,4,6-Trinitrophenyl 4-chlorobenzoate

In the title benzoate derivative, C13H6ClN3O8, the planes of the benzene rings form a dihedral angle of 63.46 (5)°. The dihedral angles between the benzene ring and its nitro groups are 12.78 (16)° for the first ortho, 28.4 (4) and 17.4 (4)° for the second (disordered) ortho and 3.58 (16)° for the para nitro group. The central ester moiety, –C—(C=O)—O–, is essentially planar (r.m.s. deviation for all non-H atoms = 0.0229 Å) and forms dihedral angles of 7.37 (14)° with the chloro-substituted benzene ring and 69.85 (6)° with the trinitro-substituted benzene ring. One of the nitro groups was refined as disordered over two sets of sites with fixed site occupancies of 0.61 and 0.39. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, forming a three-dimensional network.

(4-Chlorobenzoyl)(4-chlorophenyl)amino 3-(2-nitrophenyl)propanoate.

In the title hydroxamic acid derivate, C22H16Cl2N2O5, the nitro-substituted benzene ring forms dihedral angles of 14.11 (15) and 16.08 (15)°, with the 4-chloro­benzoyl and 4-chloro­phenyl benzene rings, respectively. The dihedral angle between the chloro-substituted benzene rings is 2.28 (13)°. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, forming chains along [100].

N-(2-Chloro-phen-yl)-1-(4-chloro-phen-yl)formamido 3-(2-nitrophenyl)-propano-ate.

In the title hydroxamic acid derivative, C22H16Cl2N2O5, the nitro-substituted benzene ring forms dihedral angles of 26.95 (15) and 87.06 (15)°, with the 4-chloro- and 2-chloro-substituted benzene rings, respectively. The dihedral angle between the chloro-substituted benzene rings is 68.19 (13)°. The O atoms of the nitro group were refined as disordered over two sets of sites with equal occupancies. In the crystal, weak C—H⋯O(=C) hydrogen bonds link mol­ecules along [100].

(Z)-4-[(2-Amino-4,5-dichloroanilino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

The mol­ecule of the title compound, C23H18Cl2N4O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 32.61 (19), 76.73 (14) and 52.57 (19)° with the three benzene rings. The secondary amino group is involved in an intra­molecular N—H⋯O hydrogen bond. In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers. An offset stacking inter­action is observed between the chloro-substituted benzene rings protruding on both sides of these dimers [centroid–centroid distance = 3.862 (1) Å].

N-(4-Chlorophenyl)-4-methoxybenzamide

In the title compound, C14H12ClNO2, the mean plane through the amide group [–N—C=O–] forms dihedral angles of 27.55 (8) and 31.94 (7)° with the meth­oxy- and chloro-substituted benzene rings, respectively. The dihedral angle between the benzene rings is 59.24 (4)°. In the crystal, N—H⋯O and weak C—H⋯O hydrogen bonds link the mol­ecules into chains along the a axis.

N-(4-chlorobenzoyl)-N-(2-chlorophenyl)-O-[2-(2-nitrophenyl)acetyl]hydroxylamine

In the title hydroxamic acid derivate, C21H14N2O5Cl2, the nitro-substituted benzene ring forms dihedral angles of 66.0 (2) and 59.6 (2)°, with the p-chloro and o-chloro-substituted benzene rings, respectively. The dihedral angle between the two chloro-substituted benzene rings is 64.2 (2) Å. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules along [010]. The crystal studied was an inversion twin with refined components in the ratio 0.60 (7):0.40 (7).

N-(2-Chlorophenyl)-1-phenylformamido 3-(2-nitrophenyl)propanoate

In the title mol­ecule, C22H17ClN2O5, the nitro-substituted benzene ring makes a dihedral angle of 79.22 (1)° with the benzoyl ring and 53.03 (1)° with the chloro-substituted benzene ring. An intra­molecular C—H⋯O hydrogen bond occurs. The crystal structure features weak C—H⋯Cl and C—H⋯O inter­actions.

N-(4-Chlorophenyl)-2,2-diphenylacetamide

In the title compound, C20H16ClNO, an S(6) ring motif is formed via an intra­molecular C—H⋯O hydrogen bond. The chloro-substituted benzene ring is almost perpendicular to the benzene rings, forming dihedral angles of 87.33 (9) and 88.69 (9)°. The dihedral angle between the benzene rings is 87.17 (9)°. In the crystal, mol­ecules are linked into chains parallel to the c axis by inter­molecular N—H⋯O hydrogen bonds. The crystal packing also features weak C—H⋯π inter­actions involving the chloro-substituted ring.

2-Anilino-4-(1,3-benzothiazol-2-yl)-5-(4-chlorobenzoyl)thiophene-3-carbonitrile

In the title compound, C25H14ClN3OS2, the central thio­phene ring [maximum deviation = 0.011 (1) Å] makes dihedral angles of 55.72 (5), 13.36 (5) and 46.77 (4)° with the adjacent chloro-substituted benzene ring, the benzene ring and the 1,3-benzothia­zole ring system [maximum deviation = 0.012 (1) Å], respectively. An intra­molecular C—H⋯S(thienyl) hydrogen bond generates an S(6) ring motif in the mol­ecule. In the crystal, mol­ecules are linked by pairs of N—H⋯N hydrogen bonds into inversion dimers and the dimers are further connected by C—H⋯O hydrogen bonds into tapes running along [100]. Aromatic π–π stacking inter­actions are also observed [centroid-to-centroid distances = 3.6116 (6) and 3.7081 (6) Å].

(N′,N′′Z,N′,N′′E)-N′,N′′-[1-(4-Chlorophenyl)ethane-1,2-diylidene]bis(3-methyl-1-benzofuran-2-carbohydrazide)

In the title compound, C28H21ClN4O4, the benzofuran ring systems make dihedral angles of 7.43 (8) and 30.92 (9)° with the chloro-substituted benzene ring. The dihedral angle between the two benzofuran ring systems is 27.41 (7)°. The two benzofuran rings are connected to the chloro-substituted benzene ring through C—N—N=C and C—N—N=C—C bridges which are nearly planar [maximum deviations = 0.003 (1) and 0.037 (1) Å]. An intra­molecular N—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by N—H⋯(O,N) and C—H⋯O hydrogen bonds into a tape along the c axis and these tapes are further connected by another weak C—H⋯O hydrogen bond into a sheet parallel to the bc plane. π–π inter­actions [centroid-to-centroid distances = 3.4845 (12)–3.6250 (13) Å] are also observed.

(Z)-3-(4-Chlorophenyl)-2-(2-phenylcyclohex-2-en-1-ylimino)thiazolidin-4-one

The title compound, C21H19ClN2OS, exists in a cis conformation with respect to the N=C bond [1.2608 (13) Å]. The cyclo­hexene ring adopts a distorted half-chair conformation. The thia­zolidine ring is close to being planar (r.m.s. deviation = 0.057 Å) and makes dihedral angles of 62.92 (6) and 56.32 (6)°, respectively, with the benzene ring and the chloro-substituted benzene ring. The dihedral angle between the benzene ring and the chloro-substituted benzene ring is 72.91 (6)°. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into undulating sheets lying parallel to the bc plane. The crystal is further consolidated by C—H⋯π inter­actions.

Ethyl 2-(4-chlorophenyl)-1-phenyl-1H-benzimidazole-5-carboxylate

In the title compound, C22H17ClN2O2, the essentially planar benzimidazole ring system [maximum deviation = 0.012 (2) Å] forms dihedral angles of 28.69 (6) and 63.65 (7)°, respectively, with the phenyl and chloro-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 64.23 (8)°. In the crystal, mol­ecules are linked into a zigzag chain along the a axis by inter­molecular C—H⋯O hydrogen bonds. C—H⋯π inter­actions are also present.