5-Pyridine 4-yl-3H-(1,3,4) Oxadiazole-2 Thione Hydrochloride Monohydrate, (I), and 4 [5-Ethylsulfanyl)-(1,3,4) Thiadiazole-2-yl]-Pyridinium Perchlorate, (II)

Abstract  

The title compounds C₇H₈ClN₃O₂S, (I), and C₉H₁₀ClN₃O₄S_2, (II), both crystallize in monoclinic space group P2₁ /c with unit cell parameters (I) a = 7.9402(7), b = 10.6312(9), c = 11.7626(10), ?, β = 99.271(5)°, Z = 4 and (II) a = 5.1439(2), b = 9.0636(4), c = 27.1814 (7), ?, β = 95.116(2)°, Z = 4. In (I) the molecule consists of a 5-pyridine-4-yl group bonded to the carbon atom at the 5 position of (1, 3, 4) oxadiazole-2 thione hydrochloride monohydrate. The angle between the mean planes of the oxadiazole and pyridine rings is 9.6(6)°. Crystal packing in (I) is stabilized by strong N–H···O hydrogen bonds in concert with a solvent water molecule and weak O–H···Cl, O–H···S, N–H···Cl intermolecular interactions. The crystal structure of compound (II) consists of 4 [5-ethylsulfanyl)-(1, 3, 4) thiadiazole-2-yl]-pyridinium perchlorate, (C₉H₁₀N₃S₂)⁺(ClO₄)⁻, cation–anion pairs, containing strong intermolecular N–H···O hydrogen bonds and weak C–H···O and N–H···O intermolecular interactions operating between the ionic species that form a cooperative hydrogen-bonded, infinite chain O–H···O–H···O–H network which generates a sheet motif structure in the unit cell. It is also supported by weak intermolecular Cg···Cg π–π and Cl–O···Cg π-ring interactions which gives additional support to molecular packing stability in the unit cell. Geometry optimized MOPAC AM1 computational calculations on each compound provides support to the structural features in their respective crystal structures.     

The Crystal Structures of (Z)-Ethyl 2-(4-chlorophenyl)-3-(2,4-difluorophenyl-amino)acrylate and its Analogues

Abstract  

The title compound, C₁₇H₁₄ClF₂NO₂, crystallizes in monoclinic space group P2₁/c with unit cell dimension of a = 16.276(3) ?, b = 7.5030(15) ?, c = 13.812(3) ?, α = 90°, β = 111.11(3)°, γ = 90° and Z = 4. The structure of the title compound reveals a Z configuration with respect to the C=C double bond in aminoacrylate fragment. The molecule is stabilized by intramolecular N–H···F and N–H···O hydrogen bonds. In the ethyl 2-aryl-3-arylaminoacrylates, electronic properties of the substituents in the aniline motif clearly affected the attached C–N bond length, and such effect is very little relative to Z-/E-configuration with respect to the C=C double bond.     

Synthesis and X-Ray Crystallographic Analysis of 2-(2, 4-Dimethyl Pyrrolyl) Benzothiazole

Abstract  

Synthesis of 2- (2, 4-dimethyl pyrrolyl) benzothiazole by chemical means and molecular structure by X-ray crystallographic techniques is reported. The compound crystallizes in the orthorhombic crystal system with space group Pbca and unit cell parameters: a = 12.161(9), b = 0.787(1), c = 16.792(2) Ǻ, V = 2202.8(4) Ǻ³ and Z = 8. The final reliability index is 0.073 for 7,959 observed reflections. The benzothiazole and pyrrole rings exist in planar conformations. The dihedral angle between the least-squares planes of both these moieties is 13.31°. There exists an isolated C4–H4···N1 intermolecular interaction, besides two C–H···S and C–H···N intermolecular interactions. The presence of C–H···S and C–H···N intramolecular interactions make the present molecule look like a virtual two-six-membered and three-five-membered ring structure.     

Crystal Structure,Conformation and Vibrational Analysis of a Mannich Base: 2-[(phenylamino) methyl]-isoindole-1,3-dione

Abstract  

The crystal structure of 2-[(phenylamino) methyl]-isoindole-1,3-dione, C₁₅H₁₂N₂O₂, crystallizes in the triclinic space group Pī with cell parameters of a = 7.1176 (2) ?, b = 8.5533 (3) ?, c = 10.9163 (4) ?, α = 95.937 (2)°, β = 102.975 (2)°, γ = 108.474 (2)°, V = 603.18 (4) ?³ and Z = 2. This indole derivative is a Mannich base in which a methyl group bridges the molecules of phthalimide and aniline molecules. The dihedral angle between the phthalimide and aniline is 75.47 (3)°. The molecules of the title compound forms a centrosymmetric hydrogen-bonded dimer through a pair of N–H···O hydrogen bonds. C–H···π and an extensive π···π interactions, in addition, stabilize the molecular structure. The compound presented here is V-shaped, the angle at the methyl bridge [N–C–N] being 115.04 (12)°. Present study reports the conformation and hydrogen bonding interactions which play an important role in biological functions. Vibration analysis complement the structure analysed.     

Synthesis and Crystal Structure Analysis of Methyl 2-Hydroxyimino-3-phenyl-propionate

Abstract  

As precursors of α-amino acids, methyl 2-hydroxyimino-3-phenyl-propionate (F.W. 193.20) was synthesized, characterized by ¹H NMR, IR, element analysis and confirmed by X-ray crystal structure analysis. This compound crystallizes in monoclinic class under the space group P2₁/c with cell parameters, a = 8.6435(17) Å, b = 5.4957(11) Å, c = 21.146(4) Å; β = 97.12(3)°, and Z = 4. The structure exhibits inter-molecular hydrogen bonds of the type O–H···N, O–H···O, C–H···O.     

Synthesis,Crystal Structure and Hydrogen-Bonding Patterns in (RS)-1-Carbamoyl Pyrrolidine-2-Carboxylic Acid

Abstract  

The title compound, N-carbamoyl-dl-proline, C₆H₁₀N₂O₃, crystallizes in the triclinic P-1 space group with unit cell parameters a = 7.610 (4) Å, b = 9.259 (5) Å, c = 11.749 (7) Å, α = 110.294 (11)°, β = 101.304 (13)°, γ = 91.391 (16)°, with two crystallographically independent molecules in the asymmetric unit. The ureido and carboxyl groups are equatorial and axial to the pyrrolidine rings, respectively. The pyrrolidine rings adopt envelope and twisted conformations in the residue A and B, respectively. The molecules are joined by N–H···O and O–H···O hydrogen bonds into cyclic structures with graph set R ₂²(8), forming infinite chains parallel to the cb plane with graph set C ₂²(14), that are further connected via N–H···O hydrogen bonds into a three-dimensional network.     

Synthesis and Crystal Structure of 2-(2,3,4-Trimethoxy-6-Methylbenzylideneamino)phenol

Abstract  The title compound 2-(2,3,4-trimethoxy-6-methylbenzylideneamino)phenol (C₁₇H₁₉NO₄, M _r = 301.33) was synthesised and characterized by elemental analysis, IR spectra and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/c, with a = 10.4458(14), b = 8.3870(10), c = 17.780(2) ?, β = 91.102(2)^°, V = 1557.4(3) ?³, Z = 4, D _c = 1.285 g/cm³, λ = 0.71073 ?, μ(Mo Kα) = 0.092 mm⁻¹, F(000) = 640. The final refinement gave R = 0.0452, wR(F ²) = 0.1065 for 2,743 observed reflections with I > 2σ(I). X-ray diffraction analysis reveals that the molecule adopts an E configuration at the C=N functional bond. The dihedral angle between the two phenyl rings is 38.3(3)°. The crystal structure is stabilized by C–H···O, O–H···O and O–H···N hydrogen bonds and π–π stacking interactions. Graphical Abstract  The title compound 2-(2,3,4-trimethoxy-6-methylbenzylideneamino)phenol (C₁₇H₁₉NO₄, M _r = 301.33) was synthesised and characterized by elemental analysis, IR spectra and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/c, with a = 10.4458(14), b = 8.387(1), c = 17.780(2) ?, β = 91.102(2)°, V = 1557.4(3) ?³, Z = 4, D _c = 1.285 g/cm³, λ = 0.71073 ?, μ(Mo Kα) = 0.092 mm⁻¹, F(000) = 640. The final refinement gave R = 0.0452, wR(F ²) = 0.1065 for 2,743 observed reflections with I > 2σ(I). X-ray diffraction analysis reveals that the molecule adopts an E configuration at the C=N functional bond. The dihedral angle between the two phenyl rings is 38.3(3)°. The crystal structure is stabilized by C–H···O and O–H···O hydrogen bonds and π–π stacking interactions.      

Synthesis and Crystal Structure of (2S,6R) Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate

Abstract  

The title compound, (2S,6R), Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (C₃₂H₃₀N₂O₂), was synthesised by the reaction of benzaldehyde, aniline and ethylacetoacetate, in the presence of l (−) proline–Fe(III) complex, formed in situ, at room temperature. The compound was characterized by spectral methods and X-ray diffraction studies. The compound crystallizes in the triclinic space group P − 1 with the following unit-cell parameters: a = 9.651(4), b = 10.909(5), c = 13.737(7) ?, α = 106.597(7), β = 108.664(8), γ = 99.779(6)°, Z = 2. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected at 100 K and refined by full-matrix least-squares procedures to a final R-value of 0.0633 for 3415 observed reflections. The 1,2,5,6-tetrahydropyridine ring exhibits a flat boat conformation. The structure has intra- and intermolecular hydrogen bonds of the type N–H···O, C–H···O and C–H···π, which help to stabilize the crystal structure.     

The Crystal Structure of 1-[2-(furan-2-yl)-6-methyl-1,2,3,4-tetrahydroquinolin-4-yl]Pyrrolidin-2-one

Abstract  

The title compound, C₁₈H₂₀N₂O₂, a potential pharmaceutical agent, crystallizes in the monoclinic P2₁/n space group with unit cell parameters a = 11.157 (7) ?, b = 8.776 (6) ?, c = 16.460 (11) ?, β = 103.08 (3)°. The tetrahydroquinoline ring system formed by the fusion of the benzene ring and the piperidine ring via two carbon atoms is coplanar, with the later adopting a sofa conformation. The pyrrolidine group in position 4 adopts an envelope conformation. Dimers related by inversion centers and linked by hydrogen bonds of the type N–H···O form cycles described by the graph set R₂²(16). Additionally, the dimers connect through weak hydrogen bonds of the type C–H···O with graph set C(10) to form chains extending along [001].     

Inter- and Intra-Molecular Hydrogen Bonding in Bis(2-amino-5-fluoro-3-methylphenyl)disulfide

Abstract  Bis(2-amino-5-fluoro-3-methylphenyl)disulfide was obtained by oxidation of 2-amino-5-fluoro-3-methylbenzenethiol and was characterized by elemental analysis, IR and ¹H-NMR spectroscopy. The X-ray structure was determined. Crystal data: C₁₄H₁₄N₂F₂S₂: Monoclinic, P2₁ /n, a = 11.8268(3), b = 9.5770(3), c = 12.3977(3) ?, β = 98.079(2)°, V = 1390.29(7) ?, Z = 4. The supramolecular structure arises because the NH₂ groups form three center S···H···F hydrogen bonds and two center N–H···F and N–H···S hydrogen bonds. Index Abstract  Inter- and Intra-Molecular Hydrogen Bonding in Bis(2-amino-5-fluoro-3-methylphenyl)disulfide J. E. Drake¹, M. B. Hursthouse², M. E. Light², R. Maheshwari³, K.G. Ojha³, R. Ratnani^3* Bis(2-amino-5-fluoro-3-methylphenyl)disulfide is linked into a three-dimensional frame work by a combination of intermolecular N–H···F and N–H···N and intramolecular N–H···S hydrogen bonds. The supramolecular structure arises because the NH₂ groups form three center S···H···F hydrogen bonds and two center N–H···F and N–H···S hydrogen bonds.      

Hydrogen Bonded 3D Supramolecular Architectures of Two Organic Salts Assembled from 2-Aminoheterocyclic Compounds and Phosphoric Acid

Abstract  

Two phosphate salts (2-aminopyrimidine): (phosphoric acid): H₂O [HL1⁺ (H₂PO₄) ⁻ ]·H₂O (1), and (4-phenylthiazol-2-amine): (phosphoric acid) [HL2⁺·(H₂PO₄)⁻] (2) based on 2-aminoheterocyclic compounds, 2-aminopyrimidine (L1), and 4-phenylthiazol-2-amine (L2) were prepared and structurally characterized by X-ray crystallography. Compound 1 crystallizes in the triclinic, space group P-1, with a = 6.2201(7) Å, b = 8.6139(9) Å, c = 9.4800(10) Å, α = 109.685(2)°, β = 106.3340(10)°, γ = 95.4450(10)°, V = 448.72(8) Å³, Z = 2. For 1, the cations were linked to each other via intermolecular C–H···N hydrogen bonds to form a 1-D chain structure running along the a-axis direction. The anions and the water molecules were connected alternatively along the a-axis direction through O–H···O hydrogen bonds to form a 1-D chain also. The cationic chains and the anionic chains were alternatively connected along the c-axis direction through N–H···O and C–H···O hydrogen bonds to form a 2D corrugated sheet. Adjacent sheets were combined together through π–π interaction to form double sheet. These double sheets were further joined together by O–H···O and N–H···O hydrogen bonds to produce a 3D network structure. Compound 2 crystallizes in the Orthorhombic, space group Pbca, with a = 10.1929(10) Å, b = 8.4406(9) Å, c = 27.589(2) Å, α = 90°, β = 90°, γ = 90°, V = 2373.6(4) Å³, Z = 8. In 2, the phosphates formed 1D chain along the b-axis through two P–O–H···O = P hydrogen bonds. The cations formed 1D zigzag chain along the b-axis direction under the CH–π interaction. The anionic chains were intercalated between two adjacent cationic chains through N–H···O, O–H···O, C–H···O, and O–S contacts. Such stacking repeated along the c-axis direction to form a 3D network structure.     

Crystal and Molecular Structure of the 1:2 Salt Formed Between 1,2-(4-Pyridyl)Ethane and 2-(4-Hydroxyphenylazo)Benzoic Acid

Abstract  Proton transfer occurred during co-crystallization of 1,2-(4-pyridyl)ethane with 2-(4-hydroxyphenylazo)benzoic acid to yield a salt comprising a 1:2 ratio of 1,2-bis(4-pyridinium)ethane dications and 2-(4-hydroxyphenylazo)benzoate anions. Centrosymmetrically related anions associate by charge-assisted O–H···O hydrogen bonds to form 24-membered {···OC₃N₂C₄OH}₂ synthons. These are connected into a supramolecular polymer via charge-assisted N–H···O hydrogen bonds involving the 1,2-bis(4-pyridinium)ethane dications. The compound crystallizes in the triclinic space group P−1 with a = 8.517(4) ?, b = 9.110(5) ?, c = 10.477(5) ?, α = 96.850(13)°, β = 94.446(12)°, γ = 104.946(10)° and Z = 1 {two anions and a dication}. Index Abstract  Supramolecular chains mediated by charge-assisted O–H···O and N–H···O hydrogen bonding are found in the salt containing a 1:2 ratio of 1,2-bis(4-pyridinium)ethane dications and 2-(4-hydroxyphenylazo)benzoate anions.      

Synthesis and Crystal Structure of Tetrabutylammonium 4-(2-Bromothiophene-5-Sulfanilamide)-Benzoate

Abstract  

Tetrabutylammonium 4-(2-bromothiophene-5-sulfanilamide)-benzoate crystallizes in C_2/C lattice with a = 18.3389(17), b = 16.540(16), c = 15.8280(15) ?, β = 116.959(2), V = 4279.5(7) ?³, Z = 4, and R = 0.0560. In the structure a very short centrosymmetric hydrogen bond and C=O···Br halogen bond interactions, together with N–H···O and C–H···O hydrogen bonds give a three-dimensional network.     

Synthesis, Crystal and Molecular Structure of 1-(2-Chlorobenzyl)-2-methylthio-1H-benzimidazole

Abstract  

1-(2-Chlorobenzyl)-2-methylthio-1H-benzimidazole compound has been synthesized and characterized by elemental analysis, IR and ¹H-NMR spectroscopy and single crystal X-ray diffraction. The compound crystallizes in the triclinic space group P-1 with unit cell parameters a = 17.201 ?, b = 5.873 ?, c = 24.791 ?, α = 67.410(10)°, β = 74.083(11)°, γ = 81.858(12)°. In the crystal packing, no classic hydrogen bonds are founded, but C–H···π interactions are being between the molecules. The molecular geometry and vibrational frequencies of (C₁₅H₁₃ClN₂S) in the ground state have been calculated by using Hartree–Fock (HF) and Density Functional Method (DFT/B3LYP) with 6-31G(d) basis set. The optimized geometric bond lengths and bond angles obtained by using HF and DFT (B3LYP) show the best agreement with the experimental data.     

Synthesis,Characterization and Crystal Structure of (<Emphasis Type="Italic">S</Emphasis>)-2-(2-Hydroxynaphthalen-6-yl)-<Emphasis Type="Italic">N</Emphasis>-((pyridin-4-yl)methyl) Propanamide

Abstract  

The synthesis, characterization and crystal structure of the title compound, (S)-2-(2-hydroxynaphthalen-6-yl)-N-((pyridin-4-yl)methyl) propanamide, is described. The salt is enantiomerically pure and crystallize in the orthorhombic P2₁2₁2₁ chiral space group with a = 7.9174(13) ?, b = 11.1583(18) ?, c = 11.2600(18) ?. Each molecule is linked to four neighboring molecules through the O–H···O and N–H···N hydrogen bonds into a supramolecular helical chain. The O–H···O and N–H···N hydrogen bonds lead to 24-membered open rings. Chains are further connected into layers via extensive interchain H···O and H···C short contacts.     

Synthesis,Crystal Structure and Antibacterial Activity of 5-Bromonicotinic Acid [1-(4-Chlorophenyl)methylidene]hydrazide Monohydrate Methanol Solvate

Abstract  The compound 5-bromonicotinic acid [1-(4-chlorophenyl)methylidene]hydrazide monohydrate methanol solvate, derived from the condensation reaction of 5-bromonicotinic acid hydrazide with 4-chlorobenzaldehyde in a methanol solution, was synthesized and characterized by elemental analysis, IR spectrum, ¹H NMR and X-ray single crystal determination. The compound crystallizes in the triclinic space group P − 1 with unit cell dimensions a = 6.9360(14) ?, b = 10.070(2) ?, c = 12.267(3) ?, α = 84.39(3)°, β = 86.10(3)°, γ = 80.50(3)°, V = 839.8(3) Ǻ³, Z = 2, R ₁ = 0.0724, and wR ₂ = 0.1720. X-ray structure determination reveals that the compound has a trans configuration with respect to the C=N double bond or C–N single bond. In the crystal structure, molecules are linked through intermolecular O–H···N, O–H···O, and C–H···O hydrogen bonds, forming layers parallel to the ab plane. The preliminary biological tests show that the compound has excellent antibacterial activity. Index Abstract  The compound 5-bromonicotinic acid [1-(4-chlorophenyl)methylidene]hydrazide monohydrate methanol solvate, derived from the condensation reaction of 5-bromonicotinic acid hydrazide with 4-chlorobenzaldehyde in a methanol solution, was synthesized and characterized by elemental analysis, IR spectrum, ¹H NMR and X-ray single crystal determination. The molecule of the compound has a trans configuration with respect to the C=N double bond or C–N single bond. In the crystal structure, molecules are linked through intermolecular O–H···N, O–H···O, and C–H···O hydrogen bonds, forming layers parallel to the ab plane. The preliminary biological tests show that the compound has excellent antibacterial activity.      

Structure and Antibacterial Activity of 3-(3,4-Dimethoxyphenyl)furan-2(5<Emphasis Type="Italic">H</Emphasis>)-ones

Abstract  

Crystalline hydrate of the title compound (5), C₁₉H₂₆N₂O₅·2(H₂O), was structurally characterized by single crystal X-ray diffraction. It crystallizes in monoclinic system space group P 21/c with a = 7.3987(7) ?, b = 17.8691(16) ?, c = 17.0022(13) ?, β = 112.944(3)°, V = 2070.0(3) ?³, Z = 4, R ₁ = 0.0592, wR ₂ = 0.1016, and T = 298(2) K. The X-ray structure determination revealed that the center furanone ring is nearly coplanar with 3,4-dimethoxybenzene ring, making a dihedral angle of 0.860(69)°. Two kinds of centrosymmetric tetramers characterized by graph-set motifs of R ₇⁸(36) and R ₄⁶(32) are formed through O–H···O, O–H···N and C–H···O hydrogen bonding interactions, which generate a sheet of edge-fused rings parallel to the (011) plane. These sheets are further linked into a three dimensional network by C–H···π interactions. Nine 3-(3,4-dimethoxyphenyl)furan-2(5H)-ones were synthesized and fully characterized by elemental analysis, MS and ¹H NMR. All of them were evaluated for antimicrobial activities against three Gram-positive organisms and a Gram-negative organism, and compound 5 was the most active against Staphylococcus aureus ATCC 25923.     

Synthesis and Crystallographic Characterization of 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1<Emphasis Type="Italic">H</Emphasis>-1,2,4-triazole: A Crucial Intermediate for the Synthesis of Azole Antifungal Drugs

Abstract  

Preparation of oxirane 3 was accomplished in two steps. 1H-1,2,4-triazole was reacted with 2,4-difluoro-α-chloroacetophenone 1 in presence of K₂CO₃ in refluxing toluene to provide compound 2. Compound 2 was treated with trimethylsulfoxonium iodide (TMSI) in aq. NaOH and toluene to provide oxirane 3. Oxirane 3, previously isolated as an oil, was crystallized from (DCM/MeOH) and characterized by X-ray crystallography: triclinic, space group P − 1, a = 7.3225 (15), b = 7.5833 (15), c = 9.856 (2) Å, α = 91.908 (12), β = 100.824 (11), γ = 103.800 (11)°, V = 520.28 (18) ų, Z = 2. The molecule has a stepped conformation with nearly parallel triazole and phenyl rings. Lack of classical hydrogen-bond donors leads to packing dominated by weaker interactions, including C–H···N, C–H···F and F···F contacts.     

Crystal Structure?4-(2,4-Dihydroxybenzylideneamino)-5-methyl-2H-1,2,4-triazol-3(4H)-one

Abstract  

The title compound (I), 4-(2,4-dihydroxybenzlideneamino)-5-methyl-2H-1,2,4-triazol-3(4H)-one was characterized by single crystal X-ray diffraction. This crystal is monoclinic, space group P2₁/c with a = 10.1447(7) ?, b = 7.0972(3) ?, c = 14.6726(10) ?, β = 98107(5)°, V = 1045.85(11) ?³, Z = 4, D _c = 1.487 g/cm³, F ₀₀ = 488, R = 0.039 and wR = 0.1025, S = 1.003, T = 293 (2) K. The title molecule is planar: the angle between the triazole ring and benzene ring is 179.1(1)°. The crystal structure contains two intramolecular (O–H···N and C–H···O) and three intermolecular interaction (O–H···N, N–H···O, and C–H···O). In addition, there is also π–π interactions.     

Structure of a New Bioactive Agent Containing Combined Antibacterial and Antifungal Pharmacophore Sites: 4-{[(<Emphasis Type="Italic">E</Emphasis>)-(5-Bromo-2-hydroxyphenyl)methylidene]amino}-<Emphasis Type="Italic">N</Emphasis>-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide

Abstract  

The title compound (3), C₁₇H₁₄BrN₃O₄S, is a Schiff base compound of 5-bromosalicylaldehyde (1) and sulfamethoxazole (2). The structure of (3) was determined by spectral (IR, ¹H and ¹³C NMR), elemental analyses and X-ray diffraction data. Compound (3) crystallizes in the monoclinic space group C2/c, with a = 31.936(3), b = 6.2571(5), c = 16.903(1) ?, β = 94.867(8), V = 3365.5(5) ?³, Z = 8. In the molecule of compound (3), the molecule is bent at the S atom with a C–SO₂–NH–C torsion angle of −86.3(3)°. Pairs of molecules, related by inversion centres, form intermolecular N–H···N hydrogen bonds to produce a dimer. An intramolecular phenolic O–H···N hydrogen bond is also formed. Intermolecular hydrogen bonding and π–π stacking hold the molecules together. The average distance between stacked benzene ring planes is 3.625(2) ?.