Hydrogen Bonding Patterns in Trimethoprimium Cinnamate 1.52 Hydrate

Abstract  

In the title compound, [C₁₄H₁₉N₄O₃ ⁺, C₉H₅ O₂ ⁻, H₂O, O0.52] the asymmetric unit contains a protonated trimethoprim cation and a cinnamate anion and two water molecules. The crystal structure was determined by single crystal X-ray diffraction. This compound crystallized in the triclinic system; space group P−1 with the unit cell parameters a = 10.010(2) ?, b = 10.339(3) ?, c = 13.486(8) ?, α = 105.32(3)°, β = 109.88(3)°, γ = 100.89(3)°, V = 1204.6(10) ?³, Z = 2. The cinnamate group is disordered. The trimethoprim (TMP) molecule is protonated at one of the pyrimidine nitrogen atoms. The carboxylate group of the cinnamate anion interacts with the protonated pyrimidine atom N1 and the 2-amino group via a pair of N–H···O hydrogen bonds, generating the R₂²(8) ring motif. The inversion related TMP cations are paired via N–H···N hydrogen bonds. In addition to the base pairing, the O1W atom bridges the 2-amino and 4-amino groups on either side of the paired bases, resulting in a self complementary DADA array. Two inversion related TMP cations and water molecules (O1W) are linked via N–H···O and O–H···O hydrogen bonds, forming a 22 membered ring with graph-set R₄⁴(22).     

Crystallographic and Conformational Analysis of [(<Emphasis Type="Italic">E</Emphasis>)-2-[(3-Chlorophenylimino)methy])-4-methoxyphenol]

Abstract  The crystal structure of C₁₄H₁₂ClNO₂ was determined by X-ray analysis. It crystallizes in the triclinic space group Pc with a = 12.5346(10) ?, b = 4.5101(3) ?, c = 12.0534(11) ?, α = 90.00o, β = 113.669(6)o, γ = 90.00o, Z = 2, Dx = 1.393 mg/m³, μ (MoK_α) = 0.298 mm⁻¹. The title compound is photochromic and molecule is non-planar. It adopts a phenol–imine tautomeric form with a strong intramolecular O–H···N hydrogen bond and a strong intermolecular C–H···O hydrogen bond. Minimum energy conformations AM1 were calculated as a function of the three torsion angles θ1(C10–C9–N1–C8), θ2(C9–N1–C8–C1) and θ3(N1–C8–C1–C6), varied every 10°. As in the X-ray experiment results, molecule has an angle that makes it non-planar between two aromatic rings in AM1 optimized geometry. Graphical Abstract  Molecular and crystal structure of [(E)-2-[(3-chlorophenylimino)methy])-4-methoxyphenol], C₁₄H₁₂ClNO₂, have been determined by single crystal X-ray diffraction study, and conformational analysis of the title molecule with respect to the selected torsion angle has been achieved by AM1 semi-empirical calculations.      

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.      

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,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.     

1-Phenyldiazenyl-8-Phenylhydrazononaphthalene-7(8H)-One-2-ol: Co-Existence of Azo-Hydroxy and Hydrazo-Keto Forms

Abstract  

The compound crystallizes in the triclinic P[`1] P\bar{1} space group and unit cell dimensions of a = 8.158 ?, b = 12.490 ?, c = 17.129 ?; α = 93.24°, β = 94.72°, γ = 97.61° and Z = 4. The structure was solved by direct methods and refined to an R1 value of 0.0890 on 2,278 observed reflections. There are two molecules in the asymmetric residue unit of the compound. In the title compound C₂₂H₁₆N₄O₂, two diazene groups at C1 and C8 and two hydroxy groups at C2 and C7 bring into play a unique azo-hydrazo equilibrium in which azo-hydroxy and hydrazo-keto forms co-exist in the molecule. The hydrazone H atom and the keto O atom are linked by an intramolecular N–H···O hydrogen bond on the other hand the hydroxy H atom and the azo N atom are linked by two intramolecular O–H···N hydrogen bonds.     

The Zolmitriptan-Pyridine (1:1) and Zolmitriptan-Propiophenone (3:2) Inclusion Complex

Abstract  

The crystal structures of zolmitriptan with pyridine (I) and propiophenone (II) solvates have been determined by single crystal X-ray diffraction studies. Compound (I) crystallizes in the orthorhombic space group P2₁2₁2₁ with a = 8.5610(5) ?, b = 12.2709(7) ?, c = 19.6201(12) ?, V = 2061.1(2) ?³, and Z = 4, while compound (II) crystallizes in the monoclinic space group P2₁ with a = 15.085(1) ?, b = 19.656(12) ?, c = 21.0860(13) ?, β = 92.068(1)°, V = 6248(4) ?³ and Z = 4. The asymmetric unit of (I), C₁₆H₂₁N₃O₂·C₅H₅N, contains one zolmitriptan molecule and one pyridine solvate, while the asymmetric unit of (II), 3(C₁₆H₂₁N₃O₂)·2(C₉H₁₀O) comprises six zolmitriptan molecules and four propiophenone solvates. In both structures, the N–H···N hydrogen bonds, form an infinite helical chain and generate a C(11)-type motif in (I) and a D₂²(13)-type motif in (II). Both the complexes have layer structures, the layers being constructed from rings (cavity) of four zolmitriptan molecules, hydrogen bonded through N–H···N and N–H···O bonds, where the pyridine (I) and propiophenone (II) solvates are included in an R₄⁴(33) ring.     

Crystal and Molecular Structure Studies of 1′-Benzyl-8-(4-fluorobenzyl)-8-azaspiro[bicyclo-[3.2.1]octane-3,4′-imidazolodine]-2′,5′-dione

Abstract  

The title compound, C₂₃H₂₃FN₃O₂ has been synthesized and the structure was investigated by X-ray diffraction studies. The compound crystallizes in the triclinic crystal class in the space group P[`1]P\overline{1} with cell parameters a = 9.345(2) ?, b = 10.940(3) ?, c = 11.986(4) ?, α = 72.349(6)°, β = 68.106(18)°, γ = 66.867(5)°, Z = 2 and V = 1027.8(5) ?³. The hydantoin ring adopts a planar conformation and is affected by the π conjugation. The pyrrolidine and piperidine rings in the bicyclo octane moiety adopt envelope and chair conformations respectively. The structure exhibits both inter and intramolecular hydrogen bonds of the type N–H···O, C–H···O and C–H···N. One of the oxygen atoms attached to the hydantoin ring simultaneously accepts two hydrogen bonds to form a three centered hydrogen bonding pattern.     

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.      

Characterization of Molecular Complexes of 1,4-Naphthoquinone Derivatives

Abstract  

The structures of sulphur atom tethered quinone containing flexible carboxylic acid (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylsulfanyl)acetic acid (1) and its molecular complex with 4,4′-bipyridine (3) are determined. The compound 1 crystallizes in P-1 (triclinic, a = 7.5378(6) ?, b = 7.6413(7) ?, c = 10.3101(9) ?; α = 89.779 (7)°, β = 81.042 (5)°, γ = 89.101(7)°) and the molecular complex 3 crystallises in P2(1)/n (monoclinic, a = 9.3383(7) ?, b = 3.970(3) ?, c = 42.130(3) ?, β = 91.056(5)°) space groups, respectively. The R₂²(8) type hydrogen bonding between dicarboxylic acid groups present in the parent compound 1 is lost on interaction with 4, 4′-bipyridine; in the molecular complex 3 R₂²(7) type of O···H–C and O–H···N interactions are present between the pyridine rings and carboxylic acid groups. The molecular complex (4) derived from 3-carboxymethylsulfanyl-1,4-dihydroxynaphthalen-2-yl-sulfanyl) acetic acid (2) with triphenylphosphine oxide in 1:2 ratio, crystallises in C2/c space group have monoclinic, a = 26.0494(13) ?, b = 10.5402(5) ?, c = 17.1023(8) ?, β = 108.719 (5)°). The triphenylphosphine oxide molecules are preferentially held by O–H···O interactions between carboxylic acid and P=O bond.     

Hydrogen-Bonded Molecular Ladders and Interlaced Networks in Complexes Built of V-Shaped Molecules 4,4′-Isopropylidenediphenol or 4,4′-Oxydibenzoic Acid with 4,4′-Bipyridine

Abstract  

The title compounds, C₁₀H₈N₂·C₁₅H₁₆O₂ (1) and C₁₀H₈N₂·C₁₄H₁₀O₅ (2), were synthesized by 4,4′-bipyridyl and two similar V-shaped molecules. The two complexes both crystallized in the same space group P2₁/n with the crystal cell parameters: a = 16.0536(3) ?, b = 6.42730(1) ?, c = 21.2717(4) ?, β = 102.330°, V = 2144.21(7) ?³, Z = 4 in compound 1 and a = 7.45020(10) ?, b = 10.0784(2) ?, c = 26.9430(5) ?, β = 92.1140(10)°, V = 2021.67(6) ?³, Z = 4 in compound 2. Compound 1 forms regular molecular chains containing alternative 4,4′-bipyridyl and 4,4′-isopropylidenediphenol units; the molecular components are linked by two types of O–H···N hydrogen bonds. Additionally, every two neighboring chains are connected to be a ladder structure by means of weak C–H···O interactions. In compound 2, 4,4′-bipyridyl and 4,4′-oxydibenzoic acid first construct one-dimensional architecture by strong O–H···N hydrogen bonds, which are similar with the interactions in compound 1. Secondly, two types of weak C–H···O contacts formed between 4,4′-bipyridyl and the acid link one-dimensional chains to be interlaced three-dimensional hydrogen-bonded networks.     

The Role of Hydrogen Bonding and Halogen Bonding in the Polymorphic Structures of 3,5-Dibromo-2,6-diaminopyridinium Bromide

Abstract  

An analysis is made of the supramolecular interactions in the two polymorphic structures of 3,5-dibromo-2,6-diaminopyridinium bromide, with particular emphasis on the roles of hydrogen and halogen bonding. Because of the extensive hydrogen bonding capabilities, hydrogen bonding interactions dominate in both phases. This causes a competition between C–Br···Br–C and C–Br···Br⁻ halogen bonding interactions, with the former dominating in the orthorhombic Pbca phase and the latter in the monoclinic P2₁/c phase. For Pbca phase a = 5.5197(11) ?, b = 15.040(3) ?, c = 23.2555(5) ?, and for P2₁/c phase a = 8.1143(19) ?, b = 14.226(3) ?, c = 8.9005(18) ?, β = 113.18(2)°.     

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, 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.     

Crystal and Molecular Structures of 2-Amino-4-Nitrobenzoic Acid and Its Cocrystals with 2,2′-Bipyridine (2/1) and Bis(pyridin-2-yl)ketone (1/1)

Abstract  

The eight-membered {···HOC=O}₂ synthon featured in the crystal structure of 2-amino-4-nitrobenzoic acid (1) is replaced by carboxylic acid···N-pyridine hydrogen bonds in its cocrystals with 2,2′-bipyridine (2/1; 2) and bis(pyridin-2-yl)ketone (1/1; 3) indicating the robust nature of the latter synthon. Disruption of the three-dimensional architecture based on O–H···O and N–H···O(nitro) hydrogen bonds in (1) is evident in the cocrystals which form supramolecular tubes (2) and chains (3) based on O–H···N and N–H···O hydrogen bonding. Compound (1) crystallizes in the monoclinic space group P2₁/n with a = 3.6291(1) ?, b = 7.7339(3) ?, c = 26.561(1) ?, β = 91.385(2)°, and Z = 4. Compound (2) crystallizes in the monoclinic space group C2/c with a = 27.562(3) ?, b = 6.8300(6) ?, c = 12.923(1) ?, β = 110.593(5)°, and Z = 4. Compound (3) crystallizes in the monoclinic space group P2₁/c with a = 3.795(3) ?, b = 12.024(8) ?, c = 35.65(2) ?, β = 92.131(6)°, and Z = 4 (determined from synchrotron data).     

Synthesis,Crystal Structure and ab Initio Studies of 5-Phenylamino-3-phenylimino-3H[1, 2]dithiole-4-carboxylic acid ethyl ester

Abstract  

5-Phenylamino-3-phenylimino-3H[1, 2]dithiole-4-carboxylic acid ethyl ester, C₁₈H₁₆N₂O₂S₂, (I), has been synthesized and the structure has been solved by X–ray diffraction. The crystals are triclinic, space group P[`1] P\bar{1} , with a = 5.7127(2) ?, b = 12.1757(5) ?, c = 14.0734(5) ?, α = 112.1217(16)°, β = 97.786(2)°, γ = 100.694(2)°, Mr = 356.45, V = 868.11(6) ?³, Z = 2 and R = 0.0373. In the title compound there is an intramolecular N–H···O hydrogen bond. The crystal structure is stabilized only by weak C–H···π and π···π interactions as well as by van der Waals forces. The geometry of the isolated molecule was optimized by ab initio quantum mechanical calculations, employing both molecular orbital Hartree-Fock (HF) and density functional theory (DFT) methods. In the DFT calculation the minimum energy was achieved for a conformation very similar to that of the solid-state molecule.     

Supramolecular Architecture via Self-Complementary Amide Hydrogen Bonding in [Ag(pia)<Subscript>2</Subscript>](NO<Subscript>3</Subscript>)·H<Subscript>2</Subscript>O: Synthesis,Thermal and Structural Studies

Abstract  

The synthesis, thermal and spectral characterization and crystal structure of silver(I) complex with picolinamide, [Ag(C₆H₆N₂O)₂](NO₃)·H₂O, are reported. The silver(I) atom is chelated by two picolinamide (pia) ligands in approximately square planar geometry. The distortion within the coordination environment is mainly imposed by formation of the chelate rings, but it is also observed in two longer (Ag–O) and two shorter (Ag–N) bond lengths. The compound crystallizes in the triclinic space group P[`1]P\bar{1} with a = 7.1265(2) ?, b = 8.9157(4) ?, c = 12.9527(4) ?, α = 83.934(3)°, β = 86.094(2)°, γ = 67.023(3)° and Z = 2. Cationic complexes are linked through amide–amide hydrogen bonds of ‘head-to-head’ R ₂²(8) motif leading to infinite chains, while nitrate anions and H₂O molecules act only as a cross-link between such four symmetry related cationic chains via hydrogen bonds forming 2D supramolecular double sheets. Therefore, the ‘head-to-head’ amide interactions in [Ag(C₆H₆N₂O)₂](NO₃)·H₂O are robust enough to accommodate the usually disruptive NO₃ ⁻ anion and H₂O molecule and could be regarded as a tool for controlling the assembly of this silver complex.     

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) ?.     

Structures of two N-{2-([(5-amino-1,3,4-thiadiazol-2-yl)difluoromethyl]-4-halophenyl}acetamides

Abstract  

The compounds, N-{2-[(5-amino-1,3,4-thiadiazol-2-yl)difluoromethyl]-4-chlorophenyl}acetamide (1: X = Cl) and N-{2([(5-amino-1,3,4-thiadiazol-2-yl)difluoromethyl]-4-bromo-phenyl}acetamide (1: X = Br), are isostructural. The molecules are near ‘‘V’’ shaped with the angles between the two aromatic planes ca. 84° in each case. The various intermolecular interactions, namely N–H···O, N–H···N, N–H···F, and C–H···N hydrogen bonds and C–H···π, C–Cl···π and C–O···π interactions, generate 3-D arrays. Compound (1: X = Cl) crystallizes in the monoclinic space group P21/c with a = 16.9032(7) ?, 10.2193(4) ?, c = 7.5227(4) ?, β = 100.179(3)° and Z = 4. Compound (1: X = Br) crystallizes in the monoclinic space group P21/c with a = 17.2119(4) ?, 10.2167(2) ?, c = 7.5677(2) ?, β = 100.326(2)° and Z = 4.