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1.  Crystal structure of 2-(4-chloro­phen­yl)-2-oxoethyl 3-bromo­benzoate 
Packing in the title keto ester compound is dominated by the formation of inversion dimers by both non-classical hydrogen bonds and offset π–π stacking inter­actions.
2-(4-Chloro­phen­yl)-2-oxoethyl 3-bromo­benzoate, C15H10BrClO3, was synthesized in a single-step reaction by condensation of 3-bromo­benzoic acid with 2-bromo-1-(4-chloro­phen­yl)ethanone in di­methyl­formamide in the presence of tri­ethyl­amine as a catalyst. The structure consists of an aryl ketone moiety linked to an aryl ester unit by a methyl­ene group. Both units are reasonably planar (r.m.s. deviations of 0.119 and 0.010 Å for the aryl ketone and aryl ester units, respectively) and are almost orthogonal, with an angle of 88.60 (3)° between them. In the crystal, mol­ecules form five separate sets of inversion dimers. Three of these are generated by two C—H⋯O inter­actions and a C—H⋯Br contact, and form chains along c and along the ab cell diagonal. In addition, two inversion-related π–π stacking inter­actions between like aryl rings again form chains of mol­ecules but in this instance along the bc diagonal. These contacts generate infinite layers of mol­ecules parallel to (011) and stack the mol­ecules along the a-axis direction.
doi:10.1107/S1600536814021643
PMCID: PMC4257351  PMID: 25484728
crystal structure; 2-(4-chloro­phen­yl)-2-oxoethyl 3-bromo­benzoate; synthesis; π–π inter­actions; inversion dimers
2.  2-(4-Chloro­phen­yl)-2-oxoethyl 4-hy­droxy­benzoate 
The title compound, C15H11ClO4, consists of a chloro­benzene ring and a phenol ring which are linked together by a 1,4-dioxo-2-oxabutane-1,4-diyl group. The dihedral angle between the chloro­benzene and phenol rings is 65.70 (11)°. In the crystal, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into chains along [010].
doi:10.1107/S1600536811037500
PMCID: PMC3201459  PMID: 22065030
3.  Crystal structure of (E)-N-{2-[2-(2-chloro­benzyl­idene)hydrazin-1-yl]-2-oxoeth­yl}-4-methyl­benzamide monohydrate 
The title compound is twisted in such a way that the almost planar [Car—C(=O)—N(H)—C(H2] and [C(H2)—C(=O)N(H)—N=C(H)—Car] segments are inclined to on another by 77.36 (8)°, while the benzene rings are inclined to one another by 89.69 (9)°. In the crystal, mol­ecules are linked via pairs of N—H⋯O hydrogen bonds, forming inversion dimers which are linked by O—H⋯O hydrogen bonds, involving the crystal water mol­ecule, forming chains propagating along the a-axis direction.
The title compound, C17H16ClN3O2·H2O, an acyl­hydrazone derivative, contains a glycine moiety and two substituted benzene rings on either end of the chain. It crystallized as a monohydrate. The mol­ecules adopt an E conformation with respect to the C=N double bond, as indicated by the N—N=C—C torsion angle of 179.38 (14)°. The mol­ecule is twisted in such a way that the almost planar Car—C(=O)—N(H)—C(H2) and C(H2)—C(=O)N(H)—N=C—Car [r.m.s deviations = 0.009 and 0.025 Å, respectively] segments are inclined to on another by 77.36 (8)°, while the benzene rings are normal to one another, making a dihedral angle of 89.69 (9)°. In the crystal, the water mol­ecule links three mol­ecules through two O—H⋯O and one N—H⋯O hydrogen bonds. The mol­ecules are linked via pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(14) ring motif. The dimers are linked by O—H⋯O hydrogen bonds, involving two mol­ecules of water, forming chains along [100], enclosing R 2 2(14) and R 2 2(18) ring motifs. The chains are linked through C—H⋯O inter­actions, forming sheets parallel to (010). Within the sheets, there are C—H⋯π and parallel slipped π–π stacking inter­actions present [inter-centroid distance = 3.6458 (12) Å].
doi:10.1107/S2056989015011147
PMCID: PMC4518978  PMID: 26279870
crystal structure; glycinyl hydrazone; monohydrate; hydrogen bonding
4.  2-[2-(2-Chloro­phen­yl)-2-oxoeth­yl]-2,3-dihydro-1λ6,2-benzothia­zole-1,1,3-trione 
The asymmetric unit of the title compound, C15H10ClNO4S, contains two independent conformers wherein the 2-chloro­phenyl group in one is rotated by approximately 180° compared to the other mol­ecule. This affects the S—N—C—C(=O) and N—C—C(=O)—C torsion angles giving vlaues of −87.0 (2) and 158.7 (2)° in one mol­ecule and −104.3 (2) and −173.4 (2)° in the other. The benzisothia­zole ring systems in the two mol­ecules are essentially planar (r.m.s. deviations = 0.017 and 0.010 Å) and form dihedral angles of 73.53 (7) and 73.26 (6)° with the benzene rings. In the crystal, there are weak π–π inter­actions between the benzene rings of the benzisothia­zole groups and symmetry-related chloro­benzene rings with centroid–centroid distances of 3.6178 (13) and 3.6267 (15) Å. In addition, pairs of weak inter­molecular C—H⋯O hydrogen bonds form inversion dimers which are connected by further C—H⋯O hydrogen bonds into a three-dimensional network.
doi:10.1107/S1600536812036653
PMCID: PMC3435829  PMID: 22969675
5.  2-(4-Chloro­phen­yl)-2-oxoethyl 3,4-dimeth­oxy­benzoate 
In the title compound, C17H15ClO5, the benzene rings forms a dihedral angle of 74.45 (10)°. In the crystal, mol­ecules are linked into C(13) chains along [011] via C—H⋯O hydrogen bonds. The crystal packing also features short Cl⋯Cl contacts of 3.1253 (10) Å.
doi:10.1107/S1600536811048264
PMCID: PMC3238996  PMID: 22199845
6.  2-(4-Chloro­phen­yl)-2-oxoethyl 2-meth­oxy­benzoate 
In the title compound, C16H13ClO4, the two benzene rings make a dihedral angle of 86.38 (8)°. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules to form columns along the a axis. The mol­ecules are also stabilized by a π–π stacking inter­action, with a centroid–centroid distance of 3.7793 (10) Å between the inversion-related benzene rings.
doi:10.1107/S1600536811021246
PMCID: PMC3151969  PMID: 21837084
7.  2-[2-(3-Chloro­phen­yl)-2-oxoeth­yl]-4-hy­droxy-3-(3-meth­oxy­benzo­yl)-2H-1λ6,2-benzothia­zine-1,1-dione 
In the title mol­ecule, C24H18ClNO6S, the heterocyclic thia­zine ring adopts a half chair conformation with the S and N atoms displaced by 0.318 (3) and 0.387 (3) Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The benzene rings of the benzothia­zin unit and meth­oxy­benzoyl group are more or less coplanar, the dihedral angle between the mean planes of these rings being 12.37 (10)° while the chloro­phenyl ring is inclined at 81.87 (4) and 73.30 (5)°, respectively, to these rings. The mol­ecular structure is consolidated by intra­molecular O—H⋯O and C—H⋯N inter­actions and the crystal packing is stabilized by weak inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536812009014
PMCID: PMC3343952  PMID: 22590033
8.  2-(4-Chloro­phen­yl)-2-oxoethyl 3-(trifluoro­meth­yl)benzoate 
In the title compound, C16H10ClF3O3, the two benzene rings are slightly twisted from each other, with a dihedral angle of 15.50 (8)° between the planes. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into a layer parallel to the bc plane.
doi:10.1107/S1600536811020629
PMCID: PMC3152104  PMID: 21837005
9.  2-(4-Chloro­phen­yl)-2-oxoethyl 2,4-di­fluoro­benzoate 
The asymmetric unit of title compound, C15H9ClF2O3, consists of two crystallographically independent mol­ecules. The dihedral angle between the two terminal benzene rings in one mol­ecule is 7.92 (14)°, while that in the other mol­ecule is 73.50 (16)°. In the crystal, mol­ecules are stacked into columns along the b axis by inter­molecular C—H⋯O hydrogen bonds. A π–π inter­action with a centroid-to-centroid distance of 3.747 (2) Å further stabilizes the crystal structure.
doi:10.1107/S1600536811020630
PMCID: PMC3151833  PMID: 21837007
10.  4-Chloro­phenyl 4-methyl­benzoate 
The crystal structure of the title compound (4CP4MBA), C14H11ClO2, resembles those of 3-chloro­phenyl 4-methyl­benzoate (3CP4MBA), 4-methyl­phenyl 4-methyl­benzoate (4MP4MBA), 4-methyl­phenyl 4-chloro­benzoate (4MP4CBA) and other aryl benzoates with similar bond parameters. The dihedral angle between the benzene rings in 4CP4MBA is 63.89 (8)°, compared with 71.75 (7)° in 3CP4MBA, 63.57 (5)° in 4MP4MBA and 51.86 (4)° in 4MP4CBA. In the crystal structure of the title compound, the mol­ecules are linked into an infinite chain along the a axis via C—H—O hydrogen bonds.
doi:10.1107/S1600536808021697
PMCID: PMC2962144  PMID: 21203226
11.  2-(4-Bromo­phen­yl)-2-oxoethyl 4-chloro­benzoate 
The asymmetric unit of the title compound, C15H10BrClO3, consists of three crystallographically independent mol­ecules. The dihedral angles between the benzene rings in the three mol­ecules are 68.8 (2), 0.7 (3) and 66.1 (2)°. In the crystal, the three independent mol­ecules are inter­connected by C—H⋯O hydrogen bonds, leading to isolated trimers.
doi:10.1107/S1600536811022963
PMCID: PMC3151903  PMID: 21837113
12.  Crystal structure of (E)-N-{2-[2-(4-methyl­benzyl­idene)hydrazin-1-yl]-2-oxoeth­yl}-p-toluene­sulfonamide 
The title compound, an aryl­sulfonyl glycinyl aryl hydrazone Schiff base, crystallizes with two independent mol­ecules in the asymmetric unit. In the crystal, a series of N—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π and slipped parallel π–π inter­actions link the mol­ecules, forming a three-dimensional structure.
The title acyl­hydrazone derivative, C17H19N3O3S, containing an amino acid moiety and electron-donating substituents attached to both the phenyl rings, crystallized with two independent mol­ecules (A and B) in the asymmetric unit. The mol­ecules are bent at the S atom, with C—SO2—NH—CH2 torsion angles of −67.3 (2) and 67.7 (3)° in mol­ecules A and B, respectively. Further, the dihedral angles between the sulfonyl­glycine segments and the p-toluene­sulfonyl rings are 76.1 (1) and 85.8 (1)° in mol­ecules A and B, respectively. The central hydrazone segments and the toluene rings attached to them are almost co-planar with their mean planes being inclined to one another by 5.2 (2) (mol­ecule A) and 2.9 (2)° (mol­ecule B). The dihedral angles between the benzene rings are 86.83 (12) (mol­ecule A) and 74.00 (14)° (mol­ecule B). In the crystal, the A mol­ecules are linked by a pair of N—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif. The dimers are linked via three N—H⋯O hydrogen bonds involving the B mol­ecules, forming chains along [100] and enclosing R 2 2(12) and R 4 4(16) ring motifs. The chains are linked via C—H⋯O hydrogen bonds and a C—H⋯π inter­action, forming sheets parallel to (010). There is a further C—H⋯π inter­action and a slipped parallel π–π inter­action [inter-centroid distance = 3.8773 (16) Å] between the sheets, leading to the formation of a three-dimensional framework.
doi:10.1107/S2056989015009330
PMCID: PMC4459384  PMID: 26090163
crystal structure; p-toluene­lsulfon­yl; glycin­yl; aryl­hydrazone; hydrogen bonding
13.  4-Chloro­phenyl 4-chloro­benzoate 
The structure of the title compound (4CP4CBA), C13H8Cl2O2, resembles those of 4-methyl­phenyl 4-chloro­benzoate (4MP4CBA), 4-chloro­phenyl 4-methyl­benzoate (4CP4MBA) and 4-methyl­phenyl 4-methyl­benzoate (4MP4MBA), with similar bond parameters. The dihedral angle between the two benzene rings in 4CP4CBA is 47.98 (7)°, compared with 51.86 (4)° in 4MP4CBA, 63.89 (8)° in 4CP4MBA and 63.57 (5)° in 4MP4MBA. In the crystal structure, mol­ecules are linked into helical chains running along the b axis by C—H—O hydrogen bonds.
doi:10.1107/S1600536808022800
PMCID: PMC2962199  PMID: 21203280
14.  2-(4-Chloro­phen­yl)-2-oxoethyl benzoate 
In the title compound, C15H11ClO3, the dihedral angle between the aromatic rings is 84.29 (8)°. In the crystal, mol­ecules are linked by weak C—H⋯π inter­actions.
doi:10.1107/S160053681102383X
PMCID: PMC3151803  PMID: 21837175
15.  2-(4-Bromo­phen­yl)-2-oxoethyl 2-methyl­benzoate 
In the title compound, C16H13BrO3, the dihedral angle formed between the bromo- and methyl-substituted benzene rings is 66.66 (8)°. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the ac plane. The crystal packing is further consolidated by C—H⋯π inter­actions.
doi:10.1107/S1600536811044564
PMCID: PMC3247503  PMID: 22220121
16.  2-(4-Bromo­phen­yl)-2-oxoethyl 4-meth­oxy­benzoate 
In the title compound, C16H13BrO4, the benzene rings are almost perpendicular to each other, making a dihedral angle of 84.07 (8)°. In the crystal, the mol­ecules are linked into chains along the a axis via inter­molecular C—H⋯O hydrogen bonds. A C—H⋯π inter­action is also observed.
doi:10.1107/S1600536811018988
PMCID: PMC3120282  PMID: 21754889
17.  Crystal structures of 2,3-bis­(4-chloro­phen­yl)-1,3-thia­zolidin-4-one and trans-2,3-bis­(4-chloro­phen­yl)-1,3-thia­zolidin-4-one 1-oxide 
In the related title compounds, (1) and (2), the 3-thia­zolidine ring pucker is twisted on the S—Cmethine bond in (1), while in (2), the ring has an envelope conformation with the S atom as the flap. In the crystal of (1), mol­ecules are linked by C—H⋯O hydrogen bonds forming chains along [100], while in the crystal of (2), mol­ecules are linked by C—H⋯O and C—H⋯Cl hydrogen bonds forming slabs parallel to (001).
In the crystal structures of the title compounds, C15H11Cl2NOS, (1), and C15H11Cl2NO2S, (2), wherein (2) is the oxidized form of (1), the thia­zolidine ring is attached to two chloro­phenyl rings. The chloro­phenyl ring on the 2-carbon atom position points in the same direction as that of the S atom in (1), while in (2), the S atom points in the opposite direction. The O atom on the chiral S atom in (2) is trans to the chloro­phenyl ring on the 2-carbon. The chloro­phenyl ring planes in each structure are close to orthogonal, making dihedral angles of 78.61 (6) and 87.46 (8)° in (1) and (2), respectively. The thia­zolidine ring has a twisted conformation on the S—Cmethine bond in (1), and an envelope conformation with the S atom 0.715 (3) Å out of the plane of other four atoms in (2). In the crystal of (1), mol­ecules are linked by C—H⋯O hydrogen bonds, as well as by slipped parallel π–π inter­actions [inter-centroid distance = 3.840 (3) Å] between inversion-related phenyl rings, forming sheets parallel to (001). In the crystal of (2), mol­ecules are linked via C—H⋯O and C—H⋯Cl hydrogen bonds, forming slabs parallel to (001).
doi:10.1107/S2056989015001954
PMCID: PMC4350739  PMID: 25844183
crystal structure; thia­zolidine; thia­zolidin-4-one 1-oxide; hydrogen bonds; π–π inter­actions
18.  Crystal structures of 4-chloro­phenyl N-(3,5-di­nitro­phen­yl)carbamate and phenyl N-(3,5-di­nitro­phen­yl)carbamate 
In the title compounds, the planes of the two aromatic rings are inclined to one another by 7.60 (8) and76.19 (8)°. In the crystals of both compounds, mol­ecules are linked via N—H⋯O hydrogen bonds, forming chains along [010].
The title compounds, C13H8ClN3O6, (I), and C13H9N3O6, (II), differ in the orientation of the two aromatic rings. In (I), they are essentially coplanar, making a dihedral angle of 8.2 (1)°, while in (II), they are inclined to one another by 76.2 (1)°. The two nitro groups are essentially coplanar with the attached benzene rings, as indicated by the dihedral angles of 1.4 (2) and 2.3 (2)° in (I), and 4.96 (18) and 5.4 (2)° in (II). The carbamate group is twisted slightly from the attached benzene ring, with a C—N—C—O torsion angle of −170.17 (15)° for (I) and 168.91 (13)° for (II). In the crystals of of both compounds, mol­ecules are linked via N—H⋯O hydrogen bonds, forming chains propagating along [010]. In (I), C—H⋯O hydrogen bonds also link mol­ecules within the chains. The crystal packing in (I) also features a very weak π–π inter­action [centroid–centroid distance = 3.7519 (9) Å].
doi:10.1107/S2056989015010245
PMCID: PMC4518992  PMID: 26279857
crystal structure; carbamate; 3,5-di­nitro­phenyl­carbamate; hydrogen bonding
19.  2-(4-Bromo­phen­yl)-2-oxoethyl anthracene-9-carboxyl­ate 
In the title compound, C23H15BrO3, the anthracene ring system is essentially planar [maximum deviation = 0.29 (2) Å] and makes a dihedral angle of 5.74 (8)° with the mean plane of the bromo-substituted benzene ring. An intra­molecular C—H⋯O hydrogen bond generates an S(9) ring motif. In the crystal, mol­ecules are linked by C—H⋯O inter­actions, forming a two-dimensional network parallel to the ac plane. π–π stacking inter­actions are observed between benzene rings [centroid–centroid distances = 3.5949 (14) and 3.5960 (13) Å].
doi:10.1107/S1600536812022684
PMCID: PMC3379439  PMID: 22719637
20.  2-(4-Bromo­phen­yl)-2-oxoethyl 4-methyl­benzoate 
The title compound, C16H13BrO3, consists of a toluene ring and a bromo­benzene ring which are linked together by a 2-oxopropyl acetate group. The dihedral angle formed between the toluene and bromo­benzene rings is 80.70 (7)°. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network.
doi:10.1107/S1600536811045272
PMCID: PMC3238827  PMID: 22199680
21.  2-(4-Bromo­phen­yl)-2-oxoethyl 2-meth­oxy­benzoate 
In the title mol­ecule, C16H13BrO4, the dihedral angle between the benzene rings is 85.92 (10)°. In the crystal, mol­ecules are linked into chains along [100] via weak inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536811023002
PMCID: PMC3152007  PMID: 21837114
22.  2-[2-(2-Bromo­phen­yl)-2-oxoeth­yl]-1λ6,2-benzothia­zole-1,1,3-trione 
The asymmetric unit of the title compound, C15H10BrNO4S, contains two different conformers in which the benzisothia­zole rings are essentially planar, with r.m.s. deviations of 0.012 and 0.017 Å. The mean planes of the benzene rings form dihedral angles 70.49 (13) and 72.79 (11)° with the benzisothia­zole rings. The orientation of the Br atoms in the two conformers exhibit the most pronounced difference, with opposing orientations in the two mol­ecules. The crystal structure is stabilized by π–π inter­actions between the benzene rings of the benzisothia­zole moieties of one mol­ecule and bromo­benzene rings of the other mol­ecule, with distances between the ring centroids of 3.599 (3) and 3.620 (3) Å, respectively. The crystal packing is further consolidated by pairs of weak inter­molecular C—H⋯O hydrogen bonds, which form inversion dimers.
doi:10.1107/S1600536812022428
PMCID: PMC3379449  PMID: 22719647
23.  Crystal structures of methyl (E)-3-(2-chloro­phen­yl)-2-({2-[(E)-2-nitro­vin­yl]phen­oxy}meth­yl)acrylate and methyl (E)-2-({4-chloro-2-[(E)-2-nitro­vin­yl]phen­oxy}meth­yl)-3-(2-chloro­phen­yl)acrylate 
In the title compounds, (I) and (II), both of which crystallize in the monoclinic space group P21/n, the methyl acrylate and nitro­vinyl units are relatively planar with an E conformation about the C=C bonds. The two aromatic rings are inclined to one another by 74.87 (9) and 75.65 (2)° for compounds (I) and (II), respectively. In the crystal of (I), chains along the b axis are formed via C—H⋯O hydrogen bonds. In the crystal of (II), mol­ecules are linked by C—H⋯O hydrogen bonds, forming sheets parallel to the ac plane.
The title compounds, C19H16ClNO5, (I), and C19H15Cl2NO5, (II), both crystallize in the monoclinic space group P21/n. They differ essentially in the orientation of the methyl acetate group, with the C=O bond directed towards the NO2 group in (I) but away from it in (II). In compound (I), the mean plane of the methyl acrylate unit is planar, with a maximum deviation of 0.0044 (2) Å for the methyl C atom, while in (II) this deviation is 0.0147 Å. The inter­planar angles between the two aromatic rings are 74.87 (9) and 75.65 (2)° for compounds (I) and (II), respectively. In both compounds, the methyl acrylate and nitro­vinyl groups each adopt an E conformation about the C=C bond. In the crystal of (I), mol­ecules are linked by C—H⋯O hydrogen bonds forming chains along the b axis. The chains are linked via C—H⋯Cl hydrogen bonds, forming sheets parallel to the ab plane. The sheets are linked via C—H⋯π inter­actions, forming a three-dimensional structure. In the crystal of (II), mol­ecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(30) ring motif. The dimers are linked via C—H⋯O hydrogen bonds, forming sheets parallel to the ac plane and enclosing R 4 4(28) ring motifs. The sheets are linked via parallel slipped π–π inter­actions (inter­centroid distances are both ca 3.86 Å), forming a three-dimensional structure.
doi:10.1107/S2056989016001493
PMCID: PMC4770962  PMID: 26958402
crystal structure; 2-cyano­acrylates; phenyl acrylates; cinnamic acid derivatives; C—H⋯O hydrogen bonding
24.  2-(4-Fluoro­phen­yl)-2-oxoethyl 4-meth­oxy­benzoate 
In the title compound, C16H13FO4, the dihedral angle between the benzene rings is 84.28 (8)°. In the crystal, C—H⋯F and C—H⋯O hydrogen bonds link the mol­ecules to form a three-dimensional network. The crystal structure is consolidated by C—H⋯π inter­actions and short F⋯F contacts [2.7748 (14) Å] also occur.
doi:10.1107/S1600536811049233
PMCID: PMC3239086  PMID: 22199934
25.  2-(2,4-Dichloro­phen­yl)-2-oxoethyl 4-meth­oxy­benzoate 
In the title compound, C16H12Cl2O4, the dihedral angle between the benzene rings is 70.11 (6)°. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds into a three-dimensional network. A C—H⋯π inter­action is also observed.
doi:10.1107/S1600536811048720
PMCID: PMC3239022  PMID: 22199870

Results 1-25 (454140)