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1.  (4-Chloro­phen­yl)(3,6-dibromo-2-hy­droxy-7-meth­oxy-1-naphth­yl)methanone 
The asymmetric unit of the title compound, C18H11Br2ClO3, contains two crystallographically independent mol­ecules in which the dihedral angles between the naphthalene ring systems and the benzene rings are 55.64 (11) and 60.50 (11)°. In each mol­ecule, an intra­molecular O—H⋯O=C hydrogen bond generates a six-membered ring. In the crystal structure, inter­molecular C—H⋯O and C—H⋯Cl hydrogen bonds and two different Br⋯O halogen bonds [2.9850 (19) and 3.2169 (19) Å] are observed.
doi:10.1107/S1600536810023299
PMCID: PMC3007072  PMID: 21587976
2.  6-(2-Chloro­benz­yl)-1-(4-chloro­phen­yl)-7-hy­droxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one 
The title compound, C19H15Cl2N3O2, was obtained by a one-step cyclo­condensation of 2-amino-1-(4-chloro­phen­yl)imidazoline with diethyl (2-chloro­benz­yl)malonate under basic conditions. In the crystalline state, the mol­ecule exists as the 7-hy­droxy-5-oxo tautomer. The dihedral angles between the fused imidazopyrimidine and aromatic chloro­phenyl and chloro­benzyl rings are 14.2 (1) and 70.7 (1)°, respectively. The conformation of the mol­ecule is influenced by the intra­molecular C—H⋯O and C—H⋯N hydrogen bonds, giving a nearly planar five-ring fused system [maximum deviation from the mean plane = 0.296 (2) Å]. In the crystal structure, strong inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into chains along the c axis. These chains are further stabilized by weak C—H⋯Cl and π–π inter­actions [centroid–centroid distance = 3.6707 (12) Å].
doi:10.1107/S160053681003919X
PMCID: PMC3009369  PMID: 21588948
3.  Crystal structure of N-[3-(2-chloro­benzo­yl)-5-ethyl­thio­phen-2-yl]-2-[(E)-(2-hy­droxy­benzyl­idene)amino]­acetamide 
In the title compound, C22H19ClN2O3S, the dihedral angle between the mean planes of the thio­phene ring and the chloro­phenyl and hy­droxy­phenyl rings are 70.1 (1) and 40.2 (4)°, respectively. The benzene rings are twisted with respect to each other by 88.9 (3)°. The imine bond lies in an E conformation. Intra­molecular O—H⋯N and N—H⋯O hydrogen bonds each generate S(6) ring motifs. In the crystal, weak C—H⋯O inter­actions link the mol­ecules, forming chains along the c axis and zigzag chains along the b axis, generating sheets lying parallel to (100).
doi:10.1107/S1600536814018224
PMCID: PMC4186110  PMID: 25309197
crystal structure; thio­phene derivatives; Schiff bases; hydrogen bonding
4.  2-[(2-Chloro­phen­yl)(hy­droxy)meth­yl]phenol 
In the title compound, C13H11ClO2, the dihedral angle between the mean planes of the 2-chloro­phenyl and phenol rings is 87.4 (9)°. The methyl hy­droxy group lies nearly perpendicular to the plane of its attached benzene ring [O—C—C—C torsion angle = 84.3 (3)°]. The two hy­droxy groups lie on the same side of the mol­ecule and are in a slightly twisted gauche conformation [O—C—C—O torsion angle = 77.1 (8)°] to each other. In the crystal, O—H⋯O hydrogen bonds between nearby methyl­hydroxy groups form dimers in alternating pairs aligned diagonally along the b axis. A view along the c axis reveals a hexa­meric aggregate mediated by a ring of six O—H⋯O hydrogen bonds generating an R 6 6(12) motif loop.
doi:10.1107/S1600536813018667
PMCID: PMC3793743  PMID: 24109330
5.  4-Chloro-N′-(3,5-dibromo-2-hy­droxy­benzyl­idene)benzohydrazide 
The asymmetric unit of the title compound, C14H9Br2ClN2O2, contains two independent mol­ecules. Both mol­ecules adopt an E configuration about the C=N bond. The dihedral angles between the benzene rings are 30.0 (2) and 51.6 (2)° in the two mol­ecules. In the crystal, mol­ecules are linked through N—H⋯O hydrogen bonds, forming chains along the b axis. In addition, there is an intra­molecular O—H⋯N hydrogen bond in each mol­ecule.
doi:10.1107/S1600536812009786
PMCID: PMC3344145  PMID: 22606148
6.  3-Chloro-N′-(3,5-dibromo-2-hy­droxy­benzyl­idene)benzohydrazide methanol monosolvate 
The title Schiff base compound, C14H9Br2ClN2O2·CH3OH, features an intra­molecular O—H⋯N hydrogen bond, which contributes to the planarity of the mol­ecule: the dihedral angle between the two benzene rings is 4.6 (2)°. In the crystal, pairs of adjacent mol­ecules are linked through inter­molecular N—H⋯O and O—H⋯O hydrogen bonds, forming dimers. The methanol solvent mol­ecule is linked by inter­molecular O—H⋯O hydrogen bonds.
doi:10.1107/S1600536811000742
PMCID: PMC3051720  PMID: 21523014
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.  3-(3-Chloro-2-hy­droxy­phen­yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
In the title compound, C16H11ClN2O2, the pyrazole ring makes dihedral angles of 11.88 (13) and 22.33 (13)° with the 3-chloro-2-hy­droxy­benzene group and phenyl rings, respectively. The phenolic hy­droxy group forms an intra­molecular O—H⋯N hydrogen bond with the imine N atom of the pyrazole unit. The formyl group is virtually coplanar with the pyrazole ring [dihedral angle = 4.5 (19)°] and acts as an acceptor in an intra­molecular C—H⋯O hydrogen bond closing seven-membered ring. In the crystal, adjacent mol­ecules are linked through C—H⋯O hydrogen bonds into infinite chains along the b axis.
doi:10.1107/S1600536811038025
PMCID: PMC3201353  PMID: 22058800
9.  2-[(E)-(3-Carb­oxy-4-hy­droxy­phen­yl)iminiometh­yl]-4-chloro­phenolate 
The title Schiff base compound, C14H10ClNO4, has been synthesized by the reaction of 5-amino-2-hy­droxy­benzoic acid and 5-chloro-2-hy­droxy­benzaldehyde. The mol­ecule is a zwitterion in the crystal, with the phenolic hy­droxy group deprotonated and the imine N atom protonated. It adopts an E configuration about the central C=N double bond. The dihedral angle between the two benzene rings is 3.83 (7)°. Intra­molecular N—H⋯O and O—H⋯O hydrogen bonding generates S(6) ring motifs. In the crystal, mol­ecules are connected by inter­molecular O—H⋯O and C—H⋯Cl hydrogen bonds, forming a supra­molecular chain.
doi:10.1107/S1600536810033362
PMCID: PMC3007861  PMID: 21588784
10.  {5-Chloro-2-[(2-hy­droxy­benzyl­idene)amino]­phen­yl}(phen­yl)methanone 
The title Schiff base compound, C20H14ClNO2, adopts an E configuration about the azomethine bond. The phenol and chloro­benzene rings form dihedral angles of 84.71 (9) and 80.70 (8)°, respectively, with the phenyl ring and are twisted by 15.32 (8)° with respect to one another. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond, which forms an S(6) ring motif. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds, forming columns parallel to the a axis.
doi:10.1107/S1600536811048690
PMCID: PMC3239075  PMID: 22199923
11.  Crystal structure of (3,5-di­chloro-2-hy­droxy­phen­yl){1-[(naphthalen-1-yl)carbon­yl]-1H-pyrazol-4-yl}methanone 
The title compound is a 1,4-diaroyl pyrazole derivative and has three aromatic rings. In the crystal, mol­ecules are linked through stacking inter­actions between the pyrazole rings and between the naphthalene and phenyl rings, and through inter­molecular C—H⋯O hydrogen bonds to form inversion dimers.
The title compound, C21H12Cl2N2O3, is a 1,4-diaroyl pyrazole derivative and has three aromatic rings. The dihedral angles between the naphthalene ring system and the pyrazole ring, the pyrazole and phenyl rings and the naphthalene ring system and the phenyl ring are 49.44 (13), 49.87 (16) and 0.58 (11)°, respectively. The phenolic proton forms an intra­molecular O—H⋯O hydrogen bond with an adjacent carbonyl O atom. In the crystal, the mol­ecules are linked through stacking inter­actions between the pyrazole rings [centroid–centroid distances = 3.546 (3)] and between the naphthalene ring system and the phenyl ring [centroid–centroid distances = 3.609 (4) Å] along the a-axis direction. The mol­ecules are further connected through C—H⋯O hydrogen bonds, forming inversion dimers.
doi:10.1107/S1600536814024684
PMCID: PMC4257447  PMID: 25552982
crystal structure; diaroyl pyrazole; cyclization; stacking inter­action; C—H⋯O hydrogen bonding
12.  Crystal structure of 9-(3-bromo-5-chloro-2-hydroxy­phen­yl)-10-(2-hy­droxy­eth­yl)-3,3,6,6-tetra­methyl-3,4,6,7,9,10-hexa­hydro­acridine-1,8(2H,5H)-dione 
The structure of a hydroacridine with significant pharmaceutical potential is reported. The acridinone ring system is in the shape of a shallow V with the majority of the ring system substituents on its convex surface; a plethora of classical and non-classical hydrogen bonds stack the molecules into interconnected columns.
The title compound C25H29BrClNO4, comprises a 3,3,6,6-tetra­methyl­tetra­hydro­acridine-1,8-dione ring system that carries a hy­droxy­ethyl substituent on the acridine N atom and a 3-bromo-5-chloro-2-hy­droxy­phenyl ring on the central methine C atom of the di­hydro­pyridine ring. The benzene ring is inclined to the acridine ring system at an angle of 89.84 (6)° and this conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond between the hy­droxy substituent on the benzene ring and one of the carbonyl groups of the acridinedione unit. In the crystal, O—H⋯O, C—H⋯O and C—H⋯Br hydrogen bonds combine to stack mol­ecules in inter­connected columns propagating along the a-axis direction.
doi:10.1107/S1600536814009556
PMCID: PMC4158539  PMID: 25249850
crystal structure; acridine; hydro­acridine
13.  9-(3-Bromo-5-chloro-2-hy­droxy­phen­yl)-10-(2-hy­droxy­eth­yl)-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione 
In the title compound, C21H21BrClNO4, the dihydro­pyridine ring adopts a flattened boat conformation. The 3-bromo-5-chloro-2-hy­droxy­phenyl ring forms a dihedral angles of 84.44 (7)° with the dihydro­pyridine mean plane. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond, with an S(8) ring motif. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules, forming a three-dimensional network.
doi:10.1107/S1600536812050222
PMCID: PMC3588342  PMID: 23476467
14.  2-[(4-Chloro­phen­yl)(2-hy­droxy-5-oxo­cyclo­pent-1-en-1-yl)meth­yl]-3-hy­droxy­cyclo­pent-2-en-1-one 
There are two mol­ecules in the asymmetric unit of the title compound, C17H15ClO4, in which the dihedral angles between the five-membered rings are 57.3 (1) and 51.4 (1)°. An intra­molecular O—H⋯O hydrogen bond occurs in each mol­ecule. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds link the moleclues into chains along the b axis.
doi:10.1107/S1600536812018715
PMCID: PMC3379264  PMID: 22719462
15.  (E)-3-(4-Chloro­phen­yl)-1-(5-hy­droxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one 
There are two independent mol­ecules in the asymmetric unit of the title compound, C20H17ClO3, each having an E configuration about the –C=C– bond. The dihedral angles between the two benzene rings in the two mol­ecules are 7.17 (11) and 9.82 (11)°. In both mol­ecules, the hy­droxy group is involved in an intra­molecular O—H⋯O hydrogen bond.
doi:10.1107/S1600536811055255
PMCID: PMC3274975  PMID: 22346920
16.  10-(4-Chloro­phen­yl)-14a-hy­droxy-12-methyl-8,9,9a,10,12,13,14,14a-octa­hydro-5H-10a,14-methano­indeno­[2′,1′:4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione 
The asymmetric unit of the title compound, C26H25ClN2O3, contains two independent mol­ecules (A and B). The conformation of the two mol­ecules differs essentially in the dihedral angle involving the two benzene rings. They are inclined to one another by 52.47 (10) in A and by 31.75 (11)° in B. In both mol­ecules, the six-membered piperidin-3-one rings have chair conformations. In mol­ecule A, all four five-membered rings have twist conformations. In mol­ecule B, only three of the four five-membered rings have twist conformations. The fourth, of the inden-1-one moiety, has an envelope conformation with the spiro C atom, bonded to the N atom of the pyrrolidine ring, as the flap. A weak intra­molecular O—H⋯N hydrogen bond occurs in each independent mol­ecule while a C—H⋯O inter­action is also observed in mol­ecule A. In the crystal, pairs of O—H⋯O hydrogen bonds link the mol­ecules, forming inversion dimers with graph-set motif R 2 2(12). These dimers are further inter­connected by C—H⋯O and C—H⋯π inter­actions, forming a three-dimensional network.
doi:10.1107/S1600536813034107
PMCID: PMC3914117  PMID: 24527024
17.  N′-[(E)-1-(5-Bromo-2-hy­droxy­phen­yl)ethyl­idene]-2-chloro­benzohydrazide 
The title compound, C15H12BrClN2O2, was synthesized by the condensation of 1-(5-bromo-2-hy­droxy­phen­yl)ethanone with 2-chloro­benzohydrazide in anhydrous ethanol. The Schiff base mol­ecule displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two benzene rings is 13.74 (3)°. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N and the crystal structure by inter­molecular N—H⋯O hydrogen bonds.
doi:10.1107/S1600536811048495
PMCID: PMC3239010  PMID: 22199859
18.  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.
doi:10.1107/S160053681201029X
PMCID: PMC3344017  PMID: 22589926
19.  (2E)-3-(4-Chloro­phen­yl)-1-(4-hy­droxy­phen­yl)prop-2-en-1-one 
In the title compound, C15H11ClO2, the dihedral angle between the mean planes of the chloro­benzene and hy­droxy­benzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group makes an angle of 18.0 (1)° with the hy­droxy­phenyl ring and 11.5 (1)° with the chloro­phenyl ring. The crystal packing is stabilized by inter­molecular O—H⋯O hydrogen bonds, weak C—H⋯O, C—H⋯π and π–π stacking inter­actions [centroid–centroid distances = 3.7771 (7) and 3.6917 (7) Å].
doi:10.1107/S160053681100701X
PMCID: PMC3099984  PMID: 21754053
20.  Crystal structure of (4Z)-1-(3,4-di­chloro­phen­yl)-4-[hy­droxy(4-methyl­phen­yl)methyl­idene]-3-methyl-4,5-di­hydro-1H-pyrazol-5-one 
The title compound, C18H14Cl2N2O2, crystallizes with two mol­ecules, A and B, in the asymmetric unit. In mol­ecule A, the dihedral angles between the central pyrazole ring and pendant di­chloro­benzene and p-tolyl rings are 2.18 (16) and 46.78 (16)°, respectively. In mol­ecule B, the equivalent angles are 27.45 (16) and 40.45 (18)°, respectively. Each mol­ecule features an intra­molecular O—H⋯O hydrogen bond, which closes an S(6) ring and mol­ecule A also features a C—H⋯O inter­action. In the crystal, weak C—H⋯π interactions and aromatic π–π stacking [shortest centroid–centroid separation = 3.707 (2) Å] generate a three-dimensional network.
doi:10.1107/S160053681402114X
PMCID: PMC4257223  PMID: 25484715
crystal structure; Schiff-base pyrazole derivative; hydrogen bonding; C—H⋯π inter­actions; aromatic π–π stacking
21.  (2E)-3-[3-(Benz­yloxy)phen­yl]-1-(2-hy­droxy­phen­yl)prop-2-en-1-one 
In the title compound, C22H18O3, an intra­molecular O—H⋯O hydrogen bond stabilizes the mol­ecular structure, forming an S(6) ring motif. The central benzene ring forms a dihedral angle of 64.74 (5)° with the phenyl ring and a dihedral angle of 5.58 (5)° with the terminal benzene ring. In the crystal, mol­ecules are linked into columns along the a axis via inter­molecular C—H⋯O hydrogen bonds. C—H⋯π inter­actions involving the centroid of the hy­droxy-substituted benzene ring further stabilize the crystal structure.
doi:10.1107/S160053681101614X
PMCID: PMC3120523  PMID: 21754713
22.  Crystal structure of 2,6-bis­(2-hy­droxy-5-methyl­phen­yl)-4-phenyl­pyridinium bromide di­chloro­methane hemisolvate hemihydrate 
The asymmetric unit in the structure of the title compound, C25H22NO2 +·Br −·0.5CH2Cl2·0.5H2O, comprises two pseudosymmetry-related cations, two bromide anions, a di­chloro­methane molecule and a water mol­ecule of solvation. The two independent cations are conformationally similar with the comparative dihedral angles between the central pyridine ring and the three benzene substituent rings being 3.0 (2), 36.4 (1) and 24.2 (1)°, and 3.7 (2), 36.5 (1) and 24.8 (1)°, respectively. In the crystal, the cations, anions and water mol­ecules are linked through O—H⋯O and O—H⋯Br hydrogen bonds, forming an insular unit. Within the cations there are also intra­molecular N—H⋯O hydrogen bonds. Adjacent centrosymmetrically related aggregates are linked by π–π stacking inter­actions between the pyridine ring and a benzene ring in both cations [ring-centroid separations = 3.525 (3) and 3.668 (3) Å], forming chains extending across the ac diagonal. Voids between these chains are filled by dichloromethane molecules.
doi:10.1107/S2056989015021386
PMCID: PMC4719919  PMID: 26870547
crystal structure; ONO-type ligands; pseudosymmetry; hydrogen bonding; π–π stacking
23.  (2,4-Dihy­droxy-6-meth­oxy­phen­yl)(3,5-dihy­droxy­phen­yl)methanone monohydrate 
The title benzophenone compound, C14H12O6·H2O, was isolated from the bark of Garcinia hombroniana Pierre (Guttiferae). The mol­ecule is twisted, the dihedral angle between the two benzene rings being 59.13 (7)°. The meth­oxy group is approximately coplanar with the attached benzene ring, with a C—O—C—C torsion angle of 1.91 (18)°. The water mol­ecule is disordered over two positions in a 0.555 (19):0.445 (19) ratio. An intra­molecular O—H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure is stabilized by inter­molecular O—H⋯O hydrogen bonds. These inter­actions link the mol­ecules into sheets parallel to the ac plane. The sheets are stacked along the b axis by π–π inter­actions, with centroid–centroid distances of 3.6219 (7) Å. A weak O—H⋯π inter­action was also noted.
doi:10.1107/S1600536811037913
PMCID: PMC3201278  PMID: 22065717
24.  Crystal structure of (5-chloro-2-hy­droxy­phen­yl)(3-methyl­isoxazolo[5,4-b]pyridin-5-yl)methanone 
In the title compound, C14H9ClN2O3, the fused pyridine and isoxazole rings are approximately planar, making a dihedral angle of 1.14 (16)°. The mol­ecule is twisted with the benzene ring and the mean plane through the fused pyridine-isoxazole ring system being inclined to one another by 47.03 (13)°. There is an intra­molecular O—H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, mol­ecules are linked by C—H⋯N hydrogen bonds, forming chains propagating along [001]. The chains are linked by slipped parallel π–π inter­actions, involving inversion-related benzene rings, forming slabs lying parallel to the bc plane {inter-centroid distance = 3.770 (2) Å].
doi:10.1107/S2056989015019635
PMCID: PMC4645069  PMID: 26594574
crystal structure; polyfunctional pyridines; isoxazole; O—H⋯O hydrogen bonds; C—H⋯N hydrogen bonds
25.  (E)-2,2′-[3-(4-Chloro­phen­yl)prop-2-ene-1,1-di­yl]bis­(3-hy­droxy-5,5-di­methyl­cyclo­hex-2-en-1-one) 
The title compound, C25H29ClO4, adopts a trans conformation about the C=C double bond and the di­methyl­cyclo­hexenone rings both show an envelope conformation with the dimethyl-substituted C atom as the flap. In the mol­ecule, the hy­droxy and carbonyl groups form two intra­molecular O—H⋯O hydrogen bonds typical for xanthene derivatives. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into chains running parallel to the a-axis direction.
doi:10.1107/S1600536813020357
PMCID: PMC3793826  PMID: 24109413

Results 1-25 (561767)