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1.  1-(4-Bromo­phen­yl)-3-(3-chloro­propan­oyl)thio­urea 
The title compound, C10H10BrClN2OS, adopts a trans–cis conformation with respect to the position of the 3-chloro­propanoyl and 4-bromo­phenyl groups, respectively, against the thiono C=S bond across their C—N bonds. The benzene ring makes a dihedral angle of 9.55 (16)° with the N2CS thio­urea moiety. Intra­molecular N—H⋯O and C—H⋯S hydrogen bonds occur. In the crystal, mol­ecules are linked into chains along the c-axis direction by N—H⋯S, C—H⋯S and C—H⋯O hydrogen bonds.
PMCID: PMC4051006  PMID: 24940263
2.  O-Ethyl S-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyl­oxazolidin-3-yl]propan-2-yl} carbonodi­thio­ate 
In the title compound, C15H17NO4S2, synthesized by addition of O-ethylxanthic acid potassium salt to a diastereomeric mixture of (4R)-3-(2-chloro­propano­yl)-4-phenyl­oxazolidin-2-one, the oxazolidinone ring has a twist conformation on the C—C bond. The phenyl ring is inclined to the mean plane of the oxazolidinone ring by 76.4 (3)°. In the chain the methine H atom is involved in a C—H⋯S and a C—H⋯O intra­molecular inter­action. In the crystal, mol­ecules are linked by C—H⋯π inter­actions, forming chains along [001]. The S configuration at the C atom to which the xanthate group is attached was determined by comparison to the known R configuration of the C atom to which the phenyl group is attached.
PMCID: PMC4011202  PMID: 24860384
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.
PMCID: PMC3009019  PMID: 21589131
4.  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.
PMCID: PMC3414999  PMID: 22904986
5.  (E)-1-(4-Amino­phen­yl)-3-(2-chloro­phen­yl)prop-2-en-1-one 
The title compound, C15H12ClNO, a substituted chalcone, adopts an E configuration with respect to the C=C bond of the enone unit. The mol­ecule is not planar, as can be seen from the dihedral angle of 28.9 (2)° between the two rings which are twisted from each other. The enone segment of the mol­ecule is not coplanar with the chloro­phenyl ring, making a dihedral angle of 23.4 (3)° with it. The amino group is also not coplanar with the ring to which it is bound, making a dihedral angle of 35 (4)°. In the crystal structure, adjacent mol­ecules are linked by N—H⋯O inter­actions into one-dimensional infinite chains along the c axis, and are further stacked as one-dimensional zigzag chains down the b axis, forming two-dimensional extended networks parallel to the bc plane.
PMCID: PMC2959457  PMID: 21201210
6.  (2E)-1-(3-Chloro­phen­yl)-3-(4-chloro­phen­yl)prop-2-en-1-one 
The title compound, C15H10Cl2O, is a chalcone with 3-chloro­phenyl and 4-chloro­phenyl substituents bonded at the opposite ends of a propenone group, the biologically active region. The dihedral angle between mean planes of these two chloro-substituted benzene rings is 46.7 (7)° compared to 46.0 (1) and 32.4 (1)° in similar published sructures. The angles between the mean plane of the prop-2-en-1-one group and the mean planes of the 3-chloro­phenyl and 4-chloro­phenyl rings are 24.1 (2) and 29.63°, respectively. While no classical hydrogen bonds are present, weak inter­molecular C—H⋯π-ring inter­actions are observed, which contribute to the stability of crystal packing.
PMCID: PMC2971255  PMID: 21578256
7.  (S)-(+)-Ketamine hydro­chloride 
The crystal structure of the title compound {systematic name: (S)-(+)-N-[1-(2-chloro­phen­yl)-2-oxocyclo­hexyl]meth­anam­in­ium chloride}, C13H17ClNO+·Cl−, was determined at 90 (2) K. The (S)-(+)-ketamine hydro­chloride salt is a well known anesthetic compound and is dramatically more potent than its R isomer. In the title compound, the cyclo­hexa­none ring adopts a chair conformation with the oxo group in the equatorial orientation. The methyl­amino and 2-chloro­phenyl groups at the 2-position have an equatorial and an axial orientation, respectively. The packing of ions is stabilized by an infinite one-dimensional ⋯Cl⋯H—N—H⋯Cl⋯ hydrogen-bonding network, involving NH2 + groups as donors and chloride anions as acceptors.
PMCID: PMC2962251  PMID: 21203199
8.  (R)-Doxylaminium (R,R)-tartrate 
In the title compound (systematic name: (R)-dimeth­yl{2-[1-phenyl-1-(pyridin-2-yl)eth­oxy]eth­yl}aza­nium (R,R)-3-carb­oxy-2,3-dihy­droxy­propano­ate), C17H23N2O+·C4H5O6 −, the doxylaminium cation is protonated at the N atom. The tartrate monoanions are linked by short, almost linear O—H⋯O hydrogen bonds into chains extended along [100]. These chains are inter­linked by anion–pyridine O—H⋯N hydrogen bonds into a two-dimensional grid structure. WeakC—H⋯O inter­actions also play a role in the crystal packing. An intra­molecular hy­droxy–carboxyl­ate O—H⋯O hydrogen bond influences the conformation of the anion: the hydrogen-bonded fragment is almost planar, the maximum deviation from the mean plane being 0.059 (14) Å. In the cation, the aromatic rings are almost perpendicular [dihedral angle = 84.94 (8)°] and the conformation of the O—C—C—N chain is gauche(−), the dihedral angle is −76.6 (2)°. The absolute configuration was assigned on the basis of known chirality of the parent compound.
PMCID: PMC3344015  PMID: 22589924
9.  2-Amino-5-nitro­phenyl 2-chloro­phenyl ketone 
In the title compound, C13H9ClN2O3, an intra­molecular hydrogen bond between the carbonyl O and an amine H atom from the 2-amino­benzoyl group stabilizes the mol­ecule, keeping these two groups nearly in the same plane [dihedral angle 14.6 (6)°]. The dihedral angle between the mean planes of the planar 2-amino­benzoyl and 2-chloro­benzoyl groups is 73.8 (6)°. The crystal packing is stabilized by a collection of inter­mediate hydrogen-bonding inter­actions which forms an infinite N—H⋯O⋯H—N—H⋯O hydrogen-bonded chain along the c axis in concert with weak N—H⋯Cl inter­actions in the same direction, producing a two-dimensional inter­molecular bonding network parallel to (001). Additional weak C—Cl⋯Cg [Cl⋯Cg = 3.858 (3) Å] and N—O⋯Cg [O⋯Cg = 3.574 (1) and 3.868 (6) Å] π-ring inter­actions provide added support to the crystal stability. A MOPAC computational calculation gives support to these observations.
PMCID: PMC2977436  PMID: 21583597
10.  Benzoximate 
In the title compound [systematic name: (3-chloro-2,6-dimeth­oxy­phen­yl)(eth­oxy­imino)­methyl benzoate], C18H18ClNO5, the phenyl and chloro­dimeth­oxy­phenyl rings are linked by the eth­oxy­imino­methyl benzoate system such that they are almost perpendicular to each other with the dihedral angle between them being 85.72 (9)°. In the crystal, C—H⋯O and C—H⋯Cl hydrogen bonds between the phenyl and chloro­dimeth­oxy­phenyl rings generate R 2 2(8) rings which link the mol­ecules into zigzag chains along the b axis. Additional C—H⋯O contacts, together with weak inter­molecular C—H⋯π inter­actions, further link the mol­ecules into a three-dimensional network.
PMCID: PMC3515316  PMID: 23284536
11.  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.
PMCID: PMC3343952  PMID: 22590033
12.  1-(4-Chloro­phen­yl)-2-[4-hy­droxy-3-(3-meth­oxy­benzo­yl)-1,1-dioxo-2H-1λ6,2-benzothia­zin-2-yl]ethanone 
In the title mol­ecule, C24H18ClNO6S, the heterocyclic thia­zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.406 (5) and 0.444 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The meth­oxy­benzoyl and the chloro­phenyl rings lie roughly parallel to each other, with a dihedral angle between the mean planes of these rings of 8.86 (10)°. The mol­ecular structure is consolidated by intra­molecular O—H⋯O and C—H⋯O inter­actions and the crystal packing is stabilized by inter­molecular O—H⋯O and C—H⋯Cl hydrogen bonds.
PMCID: PMC3344017  PMID: 22589926
13.  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.
PMCID: PMC3435829  PMID: 22969675
14.  (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.
PMCID: PMC3393272  PMID: 22807829
15.  4-Formyl-2-nitro­phenyl 2-chloro­benzoate 
In the title compound, C14H8ClNO5, the benzene rings form a dihedral angle of 19.55 (9)°. The mean plane of the central ester group [r.m.s. deviation = 0.024 Å] forms dihedral angles of 53.28 (13) and 36.93 (16)°, respectively, with the nitro- and chloro-substituted rings. The nitro group forms a dihedral angle of 19.24 (19)° with the benzene ring to which it is attached. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, forming C(7) chains, which run along [100].
PMCID: PMC3885061  PMID: 24454237
16.  Crystal structure of 8-[7,8-bis­(4-chloro­benzo­yl)-7H-cyclo­penta­[a]ace­naphthylen-9-yl]naphthalene-1-carb­oxy­lic acid 
The title compound packs with a three-dimensional supra­molecular architecture via O—H⋯O, C—H⋯O and C—H⋯Cl hydrogen bonds and through C—H⋯π inter­actions.
The title compound, C40H22Cl2O4, was formed by a Michael–Aldol domino reaction sequence, which coupled acenaphthene­quinone with 4-chloro­aceto­phenone in the presence of KOH in methanol. The dihedral angles between the central cyclo­penta­[a]ace­naphthyl­ene fused-ring system (r.m.s. deviation = 0.066 Å) and the 4-chloro­benzoyl rings are 62.25 (10) and 70.19 (10)°. The dihedral angle between the central ring system and the naphthoic acid grouping is 62.46 (7)°. This twisting of the pendant rings facilitates the formation of an intra­molecular aromatic π–π stacking inter­action between the 4-chloro­benzoyl and naphthoic acid rings, with centroid–centroid distances of 3.4533 (16) and 3.5311 (16) Å, and a C—H⋯π inter­action between one of the H atoms of the central moiety and the 4-chloro­benzoyl ring with an H⋯π distance of 2.57 Å. In the crystal, carb­oxy­lic acid inversion dimers generate R 2 2(8) loops. The dimers are linked by weak C—H⋯O and C—H⋯Cl hydrogen bonds and C—H⋯π inter­actions, generating a three-dimensional architecture.
PMCID: PMC4331862
crystal structure; domino reaction; acenaphthene­quinone; 4-chloro­aceto­phenone; hydrogen bonding
17.  (Z)-Ethyl 3-[bis­(4-chloro-3-ethyl-1-methyl-1H-pyrazol-5-yl­carbon­yl)amino]-3-(4-chloro­phen­yl)-2-cyano­propanoate 
The title compound, C26H25Cl3N6O4, was prepared by the reaction of (Z)-ethyl 3-amino-3-(4-chloro­phen­yl)-2-cyano­acrylate and 4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carbonyl chloride. The dihedral angles between the chloro­benzene and the two pyrazole rings are 59.8 (2) and 33.3 (2)°. The two pyrazole rings are oriented to each other at a dihedral angle of 84.7 (2)°. The crystal packing is governed by inter­molecular C—H⋯O inter­actions, resulting in a three-dimensional network. The ethyl groups are disordered over two positions, with site-occupancy factors of 0.71/0.29 and 0.51/0.49.
PMCID: PMC2968925  PMID: 21582596
18.  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.
PMCID: PMC3515183  PMID: 23284410
19.  N-Butyl-4-chloro­benzamide 
In the title benzamide derivative, C11H14ClNO, the chloro­benzene and butyl­amine groups are each planar, with mean deviations from the planes of 0.013 and 0.030 Å, respectively, and a dihedral angle of 2.54 (9)° between the two planes. In the crystal structure, N—H⋯O hydrogen bonds link mol­ecules in rows along a. Short inter­molecular Cl⋯Cl inter­actions [3.4225 (5) Å] link these rows into sheets in the ac plane. Additional weak C—H⋯O and C—H⋯π inter­actions generate a three-dimensional network.
PMCID: PMC2960128  PMID: 21581298
20.  Bis[4-chloro-2-(quinolin-8-yl­imino­meth­yl)phenolato-κ3 N,N′,O]cobalt(III) trichlorido­methano­lcobaltate(II) 
The reaction of 4-chloro-2-(quinolin-8-yl­imino­meth­yl)phenol (HClQP) with cobalt(II) dichloride hexa­hydrate in methanol/chloro­form under solvothermal conditions yielded the title compound, [Co(C16H10ClN2O)2][CoCl3(CH3OH)]. The CoIII atom is six-coordinated in a slightly distorted octa­hedral geometry by four N atoms and two O atoms of two tridentate HClQP ligands, which are nearly perpendicular to each other, making a dihedral angle of 86.95°. The CoII atom is four-coordinated by three Cl atoms and one O atom from a methanol ligand in a distorted tetra­hedral geometry. The crystal packing is consolidated by inter­molecular O—H⋯Cl, C—H⋯Cl and C—H⋯O hydrogen bonds, forming a three-dimensional supra­molecular structure, in which [CoIICl3(CH3OH)] anions are connected via O—H⋯Cl and C—H⋯Cl hydrogen bonds into centrosymmetric dimers. Neighboring cobalt(III) complexes form dimers through C—H⋯O hydrogen bonds, as well as π–π stacking [centroid–centroid distances = 3.30 (2) Å] between the planar quinoline systems of one HClQP ligand and the phenolate ring of another.
PMCID: PMC3647815  PMID: 23723781
21.  Crystal structure of difenoconazole 
In the title compound difenoconazole [systematic name: 1-({2-[2-chloro-4-(4-chloro­phen­oxy)phen­yl]-4-methyl-1,3-dioxolan-2-yl}meth­yl)-1H-1,2,4-triazole], C19H17Cl2N3O3, the dihedral angle between the planes of the 4-chloro­phenyl and 2-chloro­phenyl rings is 79.34 (9)°, while the dihedral angle between the planes of the triazole ring and the dioxolanyl group is 59.45 (19)°. In the crystal, pairs of C—H⋯N hydrogen bonds link adjacent mol­ecules, forming dimers with R 2 2(6) loops. In addition, the dimers are linked by C—H⋯O hydrogen bonds, resulting in a three-dimensional architecture. Disorder was modeled for one C atom of the dioxolanyl group over two sets of sites with an occupancy ratio of 0.566 (17):0.434 (17).
PMCID: PMC4257337  PMID: 25484812
crystal structure; difenoconazole; triazole fungicide; hydrogen bonds
22.  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].
PMCID: PMC3007441  PMID: 21588231
23.  1-Benzhydryl-4-(4-chloro­phenyl­sulfonyl)piperazine 
The title compound, C23H23ClN2O2S, was synthesized by the nucleophilic substitution of 1-benzhydrylpiperazine with 4-chloro­phenyl­sulfonyl chloride. The piperazine ring is in a chair conformation. The geometry around the S atom is that of a distorted tetra­hedron. There is a large range of bond angles around the piperazine N atoms. The dihedral angle between the least-squares plane (p1) defined by the four coplanar C atoms of the piperazine ring and the benzene ring is 81.6 (1)°. The dihedral angles between p1 and the phenyl rings are 76.2 (1) and 72.9 (2)°. The two phenyl rings make a dihedral angle of 65.9 (1)°. Intramolecular C—H⋯O hydrogen bonds are present.
PMCID: PMC2960354  PMID: 21201390
24.  meso-(1S*,21R*)-25-Methyl-8,11,14-trioxa-22,24,25-triaza­tetra­cyclo­[,7.015,20]penta­cosa-2,4,6,15(20),16,18-hexa­ene-23-thione chloro­form monosolvate 
The title compound crystallizes as a chloro­form solvate, C20H23N3O3S·CHCl3, with two crystallographically independent units. The independent units have distinctly different inter­action patterns between the aza­crown macrocycle and the chloro­form solvent mol­ecule. In one of them, the chloro­form mol­ecule forms C—H⋯N and Cl⋯H—C hydrogen bonds with the aza­crown macrocycle (as a proton donor and an acceptor, respectively), whereas in the other, one of the chloro­form mol­ecules is bound to the aza­crown macrocycle by an attractive Cl⋯O [3.080 (3) Å] inter­action. The aza­crown macrocycles of different units are structurally similar; the aza-14-crown-3-ether ring adopts a bowl conformation with dihedral angles between the planes of the fused benzene rings of 60.7 (1) and 68.0 (1)°. The triazinane­thione ring in both cases has a sofa conformation. The crystal packing is characterized by N—H⋯S, N—H⋯O, C—H⋯Cl and C—H⋯S hydrogen bonds.
PMCID: PMC3470208  PMID: 23125652
25.  (3aS,7aS)-5-[(S)-3,3,3-Trifluoro-2-meth­oxy-2-phenyl­propano­yl]-2,3,4,5,6,7-hexa­hydro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one monohydrate 
rac-Benzyl 3-oxohexa­hydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxyl­ate was separated by chiral chromatography, and one of the enanti­omers ([α]22 D = +10°) was hydrogenated in the presence of Pd/C in methanol, producing octa­hydro-3H-pyrrolo[3,4-c]pyridin-3-one. The latter was reacted with (2R)-3,3,3-trifluoro-2-meth­oxy-2-phenyl­propanoyl chloride [(R)-(−)-Mosher acid chloride], giving rise to the title compound, C17H19F3N2O3·H2O. The present structure established the absolute configuration of the pyrrolopiperidine fragment based on the known configuration of the (R)-Mosher acid chloride. The piperidine ring has a somewhat distorted chair conformation and is cis-fused with the five-membered envelope-shaped ring; the plane of the exocyclic amide bond is approximately orthogonal to the plane of the phenyl ring, making a dihedral angle of 82.31 (3)°. The water mol­ecule acts as an acceptor to the proton of the amino group in an N—H⋯O inter­action, and as a double proton donor in O—H⋯O hydrogen bonds, generating infinite bands along the a axis.
PMCID: PMC2980001  PMID: 21580061

Results 1-25 (336929)