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1.  Dimethyl 4-(4-hy­droxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
The title mol­ecule, C17H19NO5, was prepared by a Hantzsch dihydro­pyridine synthesis from 4-hy­droxy­benzaldehyde, methyl acetoacetate and NH4HCO3. In the mol­ecular structure of the title compound, the dihydro­pyridine ring adopts a flattened boat conformation and the plane of the base of the boat forms a dihedral angle of 80.8 (2)° with the aromatic six-membered ring. The packing is stabilized by strong inter­molecular N—H⋯Ocarbon­yl, Ohydrox­y—H⋯Ocarbon­yl and weak intra­molecular C—H⋯O hydrogen bonds.
PMCID: PMC3200733  PMID: 22064645
2.  1-(4-Bromo­phen­yl)-2-ethyl­sulfinyl-2-(phenyl­selan­yl)ethanone monohydrate 
In the title hydrate, C16H15BrO2SSe·H2O, the sulfinyl O atom lies on the opposite side of the mol­ecule to the Se and carbonyl O atoms. The benzene rings form a dihedral angle of 51.66 (17)° and are splayed with respect to each other. The observed conformation allows the water mol­ecules to bridge sulfinyl O atoms via O—H⋯O hydrogen bonds, generating a linear supra­molecular chain along the b axis; the chain is further stabilized by C—H⋯O contacts. The chains are held in place in the crystal structure by C⋯H⋯π and C—Br⋯π inter­actions.
PMCID: PMC3089188  PMID: 21754419
3.  Ethyl [1-(4-bromo­phen­yl)-1-hydr­oxy-3-oxobut­yl](phen­yl)phosphinate monohydrate1  
In the title hydrate, C18H20BrO4P·H2O, a staggered conformation is found when the organic mol­ecule is viewed down the central P—C bond, with the oxo and hydroxyl groups being diagonally opposite; each of the central P and C atoms has an S-configuration. The crystal structure features supra­molecular double chains along the b axis mediated by Ohydrox­yl–H⋯Ooxo, Owater–H⋯Ooxo, and Owater–H⋯Owater hydrogen bonds.
PMCID: PMC2983684  PMID: 21580337
4.  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.
PMCID: PMC3588342  PMID: 23476467
5.  6-(4-Bromo­phen­yl)-2-eth­oxy-4-(2,4,6-trimethoxy­phen­yl)nicotinonitrile1  
In the asymmetric unit of the title nicotinonitrile derivative, C23H21BrN2O4, there are two non-planar independent mol­ecules. The central pyridine ring makes dihedral angles of 9.05 (7) and 77.06 (7)°, respectively, with the 4-bromo­phenyl and 2,4,6-trimethoxy­phenyl rings in one mol­ecule, whereas the corresponding values are 5.96 (7) and 82.37 (7)° in the other. All the three meth­oxy groups are essentially in the plane of the attached benzene ring [C—O—C—C angles = 2.99 (19), 4.8 (2) and −6.2 (2)° in one mol­ecule, and 2.69 (18), 176.73 (15) and 1.3 (2)° in the other]. The eth­oxy group is slightly twisted in one mol­ecule [C—C—O—C = 173.84 (12)°], whereas it is coplanar with the pyridine ring in the other [C—C—O—C = −177.23 (13)°]. Weak intra­molecular C—H⋯N inter­actions generate S(5) ring motifs. In the crystal structure, the mol­ecules are linked by weak inter­molecular C—H⋯N and C—H⋯O inter­actions into a supra­molecular three-dimensional network in such a way that the nicotinonitrile units of neighboring mol­ecules are stacked in an anti­parallel manner along the c axis. The crystal is further stabilized by C—H⋯π inter­actions.
PMCID: PMC2971038  PMID: 21578493
6.  Crystal structure of 5,5-bis­(4-methyl­benz­yl)pyrimidine-2,4,6(1H,3H,5H)-trione monohydrate 
Reaction of 4-methyl benzyl chloride with barbituric acid gave 5,5-bis­(4-methyl­benz­yl)pyrimidine-2,4,6(1H,3H,5H)-trione, which crystallized with two mol­ecules in its asymmetric unit along with two solvent water mol­ecules. A hydrogen-bonded sheet is formed by a combination of N—H⋯O and Owater—H⋯O hydrogen bonds, which are further inter­connected by C—H⋯πar­yl inter­actions, leading to a three-dimensional supra­molecular architecture.
The asymmetric unit of the title compound, C20H20N2O3·H2O, contains two independent mol­ecules (A and B), with similar conformations and two independent water mol­ecules. In the crystal, N—H⋯O and Owater—H⋯O hydrogen bonds link all moieties into two crystallographically independent kinds of sheets parallel to the ac plane. These independent sheets, each containing either A or B mol­ecules, are further alternately stacked along the b axis and inter­connected via C—H⋯πar­yl inter­actions.
PMCID: PMC4331871  PMID: 25705440
crystal structure; hydrogen-bonded sheets; pyrimidine; C—H⋯π inter­actions; Knoevenagel condensation; three-dimensional structure
7.  Crystal structure of ethyl 2-[9-(5-bromo-2-hy­droxy­phen­yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridin-10-yl]acetate 
In the title compound, C23H24BrNO5, the central 1,4-di­hydro­pyridine ring of the 1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine ring system adopts a half-chair conformation. The two cyclo­hexene rings fused to the central ring both have a twisted-boat conformation. The mean planes of the bromo­hydroxy­phenyl ring and the major and minor components of the disordered ethyl amino­acetate moiety make dihedral angles of 78.99 (12), 85.9 (2) and 88.3 (9)°, respectively, with the 1,4-di­hydro­pyridine ring. The terminal ethyl group of the ethyl amino­acetate moiety is disordered over two sets of sites with refined occupancies of 0.768 (17) and 0.232 (17). The mol­ecular conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond, forming an S(8) ring motif. In the crystal, C—H⋯O hydrogen bonds connect the mol­ecules into layers parallel to (001), enclosing R 1 2(7) ring motifs.
PMCID: PMC4719938  PMID: 26870566
crystal structure; acridines; hydro­acridinones; hydrogen bonding
8.  The effect of bromine scanning around the phenyl group of 4-phenyl­quinolone derivatives 
In three quinolone compounds, the 1,4-di­hydro­pyridine (1,4-DHP) rings adopt flat-boat conformations which are bisected by the plane of the pseudo-axial brominated aryl ring. The cyclo­hexanone rings adopt an envelope conformation. In all three compounds, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into extended chains. Inter­molecular halogen bonding between Br and the ester carbonyl O atom is observed in two of the compounds.
Three quinolone compounds were synthesized and crystallized in an effort to study the structure–activity relationship of these calcium-channel antagonists. In all three quinolones, viz. ethyl 4-(4-bromo­phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate, (I), ethyl 4-(3-bromo­phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-car­box­yl­ate, (II), and ethyl 4-(2-bromo­phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate, (III), all C21H24BrNO3, common structural features such as a flat boat conformation of the 1,4-di­hydro­pyridine (1,4-DHP) ring, an envelope conformation of the fused cyclo­hexa­none ring and a bromo­phenyl ring at the pseudo-axial position and orthogonal to the 1,4-DHP ring are retained. However, due to the different packing inter­actions in each compound, halogen bonds are observed in (I) and (III). Compound (III) crystallizes with two molecules in the asymmetric unit. All of the prepared derivatives satisfy the basic structural requirements to possess moderate activity as calcium-channel antagonists.
PMCID: PMC4174017  PMID: 25093361
crystal structure; structure–activity relationships; calcium-channel antagonists; quinolone compounds; halogen bonding; 1,4-di­hydro­pyridine rings; hydrogen bonding; bromine scanning
9.  Solid-state tautomeric structure and invariom refinement of a novel and potent HIV integrase inhibitor 
The conformation and tautomeric structure of (Z)-4-[5-(2,6-difluoro­benzyl)-1-(2-fluoro­benzyl)-2-oxo-1,2-dihydro­pyridin-3-yl]-4-hy­droxy-2-oxo-N-(2-oxopyrrolidin-1-yl)but-3-enamide, C27H22F3N3O5, in the solid state has been resolved by single-crystal X-ray crystallography. The electron distribution in the mol­ecule was evaluated by refinements with invarioms, aspherical scattering factors by the method of Dittrich et al. [Acta Cryst. (2005), A61, 314–320] that are based on the Hansen–Coppens multipole model [Hansen & Coppens (1978 ▶). Acta Cryst. A34, 909–921]. The β-diketo portion of the mol­ecule exists in the enol form. The enol –OH hydrogen forms a strong asymmetric hydrogen bond with the carbonyl O atom on the β-C atom of the chain. Weak intra­molecular hydrogen bonds exist between the weakly acidic α-CH hydrogen of the keto–enol group and the pyridinone carbonyl O atom, and also between the hydrazine N—H group and the carbonyl group in the β-position from the hydrazine N—H group. The electrostatic properties of the mol­ecule were derived from the mol­ecular charge density. The mol­ecule is in a lengthened conformation and the rings of the two benzyl groups are nearly orthogonal. Results from a high-field 1H and 13C NMR correlation spectroscopy study confirm that the same tautomer exists in solution as in the solid state.
PMCID: PMC3589111  PMID: 23459357
10.  1-(4-Bromo­phen­yl)-2-(phenyl­sulfon­yl)ethanone 
The overall conformation of the title mol­ecule, C14H11BrO3S, is L-shaped, as seen in the value of the dihedral angle formed between the terminal benzene rings of 75.44 (13)°. The presence of C—H⋯O inter­actions leads to the formation of linear supra­molecular chains along the a-axis direction in the crystal structure. These are connected into supra­molecular arrays in the ab plane via C—H⋯π contacts.
PMCID: PMC3201297  PMID: 22064893
11.  Dimethyl 4-(4-formyl­phen­yl)-2,6-di­methyl-1,4-dihydro­pyridine-3,5-dicar­boxyl­ate 
The title compound, C18H19NO5, is a product of the Hantzsch reaction of p-phthalaldehyde, methyl acetoacetate, and ammonium acetate. The 1,4-dihydro­pyridine ring of the mol­ecule adopts a flattened boat conformation. The benzene ring is almost perpendicular to the 1,4-dihydro­pyridine ring; the plane through the six C atoms of the benzene ring and the plane through the four C atoms that form the base of the boat-shaped 1,4-dihydro­pyridine ring (excluding the ring N atom and the opposite ring C atom) make a dihedral angle of 87.60 (3)°. Inter­molecular N—H⋯O hydrogen bonds result in the formation of extended chains along the a axis.
PMCID: PMC2915344  PMID: 21200858
12.  N-[3a-(4-Bromo­phen­yl)-8b-hy­droxy-6,8-dimeth­oxy-3-phenyl-2,3,3a,8b-tetra­hydro-1H-cyclo­penta­[b]benzofuran-1-yl]formamide monohydrate 
In the title compound, C26H24BrNO5·H2O, a synthetic analogue of natural flavagline, the cyclo­pentane ring adopts an envelope conformation (the flap atom bearing the phenyl group) and the vicinal phenyl and bromo­phenyl groups are slightly shifted relative to each other [CPh—C—C—CPhBr = 36.3 (2)°]. Intra­molecular N—H⋯O and C—H⋯O hydrogen bonds form S(5) motifs. In the crystal, the organic and the water mol­ecules are linked by an O—H⋯O hydrogen bond. Pairs of organic and water mol­ecules, located about inversion centers, inter­act through O—H⋯O hydrogen bonds, forming R 4 4(20) and R 4 4(26) motifs, which together lead to C 2 2(9) motifs. The crystal packing is also characterized by N—H⋯O and C—H⋯O hydrogen bonds between neighbouring organic mol­ecules, forming R 2 2(10) and R 2 2(18) motifs, respectively.
PMCID: PMC3588239  PMID: 23476436
13.  Crystal structures of three substituted 3-aryl-2-phenyl-2,3-di­hydro-4H-1,3-benzo­thia­zin-4-ones 
The crystal structures of three closely related benzo­thia­zinone structures are reported. All three are conformationally similar having screw-boat puckering in the thia­zine ring and C—H⋯π-type inter­molecular inter­actions in the crystals.
Three ring-substituted 3-aryl analogs of 2-phenyl-2,3-di­hydro-4H-1,3-benzo­thia­zin-4-one, namely 3-(4-meth­oxy­phen­yl)-2-phenyl-4H-1,3-benzo­thia­zin-4-one, C21H17NO2S, (I), 2-phenyl-3-[4-(tri­fluoro­meth­yl)phen­yl]-2,3-di­hydro-4H-1,3-benzo­thia­zin-4-one toluene hemisolvate, C21H14F3NOS·0.5C7H8, (II), and 3-(3-bromo­phen­yl)-2-phenyl-2,3-di­hydro-4H-1,3-benzo­thia­zin-4-one toluene hemisolvate, C20H14BrNOS·0.5C7H8, (III), were synthesized and their crystal structures determined. The hemisolvates differ in that in (II), the asymmetric unit comprises two molecules of the benzo­thia­zinone compound and a toluene solvent mol­ecule, whereas in (III), the unit comprises one benzo­thia­zinone mol­ecule and a half-occupancy toluene solvent mol­ecule. All crystals are of racemic mixtures of the chiral 2-C atom of the thia­zine moiety, which in all structures has a screw-boat puckering, with the puckering amplitude values within the range 0.575–0.603 Å. In all three structures, the benzene plane of the benzo­thia­zine system makes a dihedral angle in the range 78.60 (5) to 98.40 (5)° with the unsubstituted benzene plane and in the range 70.50 (1) to 121.00 (5)° with the substituted benzene plane. The CF3 substituent group in one of the mol­ecules of (II) shows positional disorder, with an occupancy ratio of 0.57 (3):0.43 (3). In the crystals of (I) and (II), weak inter­molecular C—H⋯O inter­actions are present, giving in (I), mol­ecules arranged in a plane parallel to (010), and in (II), chains along a. In addition, all three structures show weak C—H⋯π inter­actions involving various aromatic rings.
PMCID: PMC4971851  PMID: 27536392
crystal structure; benzo­thia­zinones; screw-boat thia­zine pucker; aromatic ring inter­actions
14.  Diethyl 2,6-dimethyl-4-(5-phenyl-1H-pyrazol-4-yl)-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
In the title compound, C22H25N3O4, the dihydro­pyridine ring adopts a flattened boat conformation. The pyrazole ring makes a dihedral angle of 29.04 (5)° with the benzene ring. The mol­ecular structure is stabilized by an intra­molecular C—H⋯O hydrogen bond which generates an S(9) ring motif. In the crystal, mol­ecules are linked via N—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ab plane. The crystal structure is further consolidated by weak C—H⋯π inter­actions.
PMCID: PMC3297939  PMID: 22412742
15.  Crystal structure of N-[4-amino-5-cyano-6-(methyl­sulfan­yl)pyridin-2-yl]acetamide hemihydrate 
The title compound, C9H10N4OS·0.5H2O, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit, together with a water mol­ecule of crystallization. The acetamide moiety, which has an extended conformation, is inclined to the pyridine ring by 7.95 (16)° in mol­ecule A and by 1.77 (16)° in mol­ecule B. In the crystal, the A and B mol­ecules are linked by two N—H⋯Ocarbon­yl hydrogen bonds, forming a dimer. The dimers are linked via N—H⋯N hydrogen bonds, forming ribbons that are linked by N—H⋯Owater hydrogen bonds to form sheets parallel to (110). The sheets are linked by O—H⋯N hydrogen bonds, forming slabs, and between the slabs there are weak slipped parallel π–π inter­actions [inter-centroid distance = 3.734 (2) Å, inter­planar distance = 3.3505 (11) Å and slippage = 1.648 Å], forming a three-dimensional structure.
PMCID: PMC4350750  PMID: 25844232
crystal structure; poly-functional pyridines; acetamide; disorder; hydrogen bonding
16.  1,1′-[4-(2,4-Dichloro­phen­yl)-2,6-di­methyl-1,4-di­hydro­pyridine-3,5-di­yl]diethanone 
In the title compound, C17H17Cl2NO2, the central 1,4-dihydro­pyridine ring adopts a flattened-boat conformation. The ethanone substituents of the dihydro­pyridine ring at positions 3 and 5 have synperiplanar (cis) or anti­periplanar (trans) conformations with respect to the adjacent C=C bonds in the dihydro­pyridine ring. The 2,4-dichloro­phenyl ring is almost planar [r.m.s. deviation = 0.0045 (1) Å] and almost perpendicular [89.27 (3)°] to the mean plane of the dihydro­pyridine ring. In the crystal, an N—H⋯O hydrogen bond links mol­ecules into a zigzag chain along the ac diagonal. C—H⋯Cl contacts form centrosymmetric dimers and additional weak C—H⋯O contacts further consolidate the packing.
PMCID: PMC3051630  PMID: 21523057
17.  Ethyl 2-methyl-5-oxo-4-(3,4,5-trimeth­oxy­phen­yl)-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate 
In the mol­ecular structure of the title compound, C22H27NO6, the dihydro­pyridine ring adopts a flattened boat conformation while the cyclo­hexenone ring is in an envelope conformation. In the crystal, mol­ecules stack parallel to the crystallographic a axis linked by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds.
PMCID: PMC3008019  PMID: 21588607
18.  Ethyl 4-(3-hydroxy­phen­yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate 
In the mol­ecular structure of the title compound, C21H25NO4, the dihydro­pyridine ring adopts a flattened boat conformation while the cyclo­hexenone ring is in an envelope conformation. In the crystal structure, mol­ecules are linked into a two-dimensional network parallel to (10) by N—H⋯O and O—H⋯O hydrogen bonds. The network is generated by R 4 4(30) and R 4 4(34) graph-set motifs.
PMCID: PMC2971334  PMID: 21578275
19.  Chlorido[(E)-2-hydr­oxy-6-(isonicotinoyl­hydrazonometh­yl)phen­yl]mercury(II) monohydrate 
The asymmetric unit of the title compound, [Hg(C13H10N3O2)Cl]·H2O, contains two independent mercury(II) complexes with slightly different conformations, related via a pseudo-inversion centre, and two water mol­ecules. The HgII atoms show a typical linear geometry to a C atom of the benzene ring and to a Cl atom. A benzene C and the azomethine N atom chelate the HgII atoms with weak intra­molecular Hg⋯N bonding distances of 2.735 (3) and 2.739 (3) Å, respectively. The resulting five-membered metallacycles are nearly coplanar with the benzene rings [dihedral angles = 0.9 (1) and 0.7 (1)°], while the pyridine rings make dihedral angles with the benzene units of 58.17 (1) and 56.58 (1)°. In the crystal structure, the HgII complexes are linked by hydr­oxy donor and pyridine acceptor groups into chains along [010]. The water mol­ecules connect the complexes through inter­molecular O—H⋯Ocarbon­yl bonds in the a-axis direction, and the azomethine H atoms donate towards the water O atoms, forming a three-dimensional network of inter­molecular O—H⋯N, O—H⋯O and N—H⋯O hydrogen bonds.
PMCID: PMC2969284  PMID: 21582756
20.  (1E)-1-(3-Bromo­phen­yl)ethanone 2,4-di­nitro­phenyl­hydrazone 
The title compound, C14H11BrN4O4, contains 3-bromo­phenyl and 2,4-dinitro­phenyl groups on opposite sides of a hydrazone unit and crystallizes with two mol­ecules in the asymmetric unit. The dihedral angles between the two ring systems in each mol­ecule are 2.0 (1) and 2.5 (4)°. Weak C—H⋯O hydrogen bonds and weak π–π stacking inter­actions [centroid–centroid distance = 3.7269 (14) Å] help to establish the packing. Intra­molecular N—H⋯O hydrogen bonds are also observed. On one of the rings, the Br atom is disordered over two equivalent positions of the phenyl ring [occupancy ratio 0.8734 (10):0.1266 (10).
PMCID: PMC3008979  PMID: 21589019
21.  N-(3-Bromo­phen­yl)acetamide 
The conformation of the N—H bond in the structure of the title compound, C8H8BrNO, is anti to the C=O bond and to the meta-bromo substituent of the aromatic ring in both independent mol­ecules comprising the asymmetric unit. Mol­ecules are linked through N—H⋯O hydrogen bonding into supra­molecular chains with a twisted topology.
PMCID: PMC2977722  PMID: 21583858
22.  2-(Benzo[d]thia­zol-2-ylsulfon­yl)-1-(4-bromo­phen­yl)ethanone 
In the title mol­ecule, C15H10BrNO3S2, the dihedral angle between the benzothia­zole ring system and the benzene ring is 67.57 (12)°. The crystal structure is stabilized by weak inter­molecular C—H⋯O inter­actions. In addition, there is an inter­molecular Br⋯C [3.379 (3) Å] contact which is shorter than the sum of the van der Waals radii of these atoms.
PMCID: PMC2980183  PMID: 21580093
23.  1-[(4-Bromo­phen­yl)(morpholin-4-yl)meth­yl]naphthalen-2-ol 
The title compound, C21H20BrNO2, was obtained from a condensation reaction of 4-bromo­benzaldehyde, 2-naphthol and morpholine. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond, closing a six-membered ring. The dihedral angle between the naphthalene ring system and the benzene ring is 76.72 (8)°. In addition to the intra­molecular hydrogen bond, the O—H groups of centrosymmetrically related mol­ecules form short inter­molecular H⋯O contacts of 2.59 Å. These mol­ecules are also linked by pairs of C—H⋯O inter­actions, generating an R 2 2(14) motif.
PMCID: PMC3275269  PMID: 22347125
24.  Diisobutyl 4-(3-eth­oxy-4-hy­droxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
The asymmetric unit of the title compound, C25H35NO6, contains two independent mol­ecules. In each mol­ecule, the 1,4-dihydro­pyridine ring adopts a flattened boat conformation. The dihedral angles between the 1,4-dihydro­pyridine and benzene rings are 87.55 (7) and 87.23 (7)°. In one of these mol­ecules, one of the isobutyl groups is disordered over two sets of sites, with an occupancy ratio of 0.890 (2):0.110 (2). In the crystal, mol­ecules are linked through N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds forming two-dimensional networks parallel to the ab plane. The crystal structure is further stabilized by weak C—H⋯π inter­actions.
PMCID: PMC3274982  PMID: 22346927
25.  4-Amino-2,3,5-trimethyl­pyridine monohydrate 
In the title compound, C8H12N2·H2O, four substituted pyridine mol­ecules alternate with four water mol­ecules, forming a large ring via Owater—H⋯Npyridine and Namine—H⋯Owater hydrogen bonding. Adjacent rings are connected via Owater—H⋯Owater hydrogen-bonds, forming a three-dimensional network.
PMCID: PMC2969585  PMID: 21583183

Results 1-25 (397422)