N-(4-Methyl­phen­yl)-N′-phenyl­butane­diamide monohydrate

B S Saraswathi; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811018915

. 2011 May 25;67(Pt 6):o1495. doi: 10.1107/S1600536811018915

N-(4-Methylphenyl)-N′-phenylbutanediamide monohydrate

B S Saraswathi ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*

PMCID: PMC3120322 PMID: 21754863

Abstract

In the title hydrate, C₁₇H₁₈N₂O₂·H₂O, the dihedral angles formed by the aromatic rings of the benzene and methylbenzene groups with the mean planes of the attached NH—C(O)—CH₂ fragments are 12.6 (4) and 23.3 (3)°, respectively, while that between the two aromatic rings is 73.7 (2)°. In the crystal, the water molecule accepts two and makes two hydrogen bonds. The molecules are packed into layers parallel to (101) by O—H⋯O and N—H⋯O hydrogen-bonding interactions.

Related literature

For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2000 ▶); Saraswathi et al. (2011a ▶,b ▶) and on the structures of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ▶). For restrained geometry, see: Nardelli (1999 ▶).

Experimental

Crystal data

C₁₇H₁₈N₂O₂·H₂O
M _r = 300.35
Monoclinic,
a = 15.242 (4) Å
b = 4.905 (1) Å
c = 21.540 (5) Å
β = 102.90 (2)°
V = 1569.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.44 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.962, T _max = 0.993
5068 measured reflections
2805 independent reflections
1356 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.117
wR(F ²) = 0.239
S = 1.16
2805 reflections
211 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018915/tk2744sup1.cif

e-67-o1495-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018915/tk2744Isup2.hkl

e-67-o1495-Isup2.hkl^{(137.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811018915/tk2744Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.85 (2)	2.06 (2)	2.895 (6)	168 (6)
N2—H2N⋯O3ⁱⁱ	0.86 (2)	2.15 (2)	2.992 (6)	169 (5)
O3—H31⋯O1	0.85 (2)	1.93 (2)	2.762 (6)	165 (5)
O3—H32⋯O3ⁱⁱⁱ	0.85 (2)	2.03 (2)	2.858 (5)	166 (5)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

BSS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

supplementary crystallographic information

Comment

The amide and sulfonamide moieties are important constituents of many biologically significant compounds. As a part of a study of the substituent effects on their structures and other aspects of this class of compounds (Gowda et al., 2000, 2007; Saraswathi et al., 2011a,b), in the present work, the structure of the title compound, isolated as a monohydrate has been determined (Fig. 1). The conformation of N—H and C═ O bonds in each C—NH—C(O)—C segment is anti, similar to that observed in N,N-bis(2-methylphenyl)- succinamide (II) (Saraswathi et al., 2011a) and in N,N-bis(3-chlorophenyl)-succinamide (III) (Saraswathi et al., 2011b).

The dihedral angle between the phenyl ring and the adjacent NH—C(O)—CH₂ segment is 12.6 (4) ° and that between the 4-methylphenyl ring and the adjacent NH—C(O)—CH₂ segment is 23.3 (3) °, compared to the values of 62.1 (2) ° formed between the benzene ring and the NH—C(O)—CH₂ segment in the two halves of (II), and 32.8 (1) ° in (III). In the title compound, the dihedral angle between the two aromatic rings is 73.7 (2) °. The crystal packing is stabilized through N1—H1N···O2, N2—H2N···O3, O3—H31···O1 and O3—H32···O3 hydrogen bonding (Table 1) and results in layers as shown in Fig.2.

Experimental

Succinic anhydride (0.01 mol) in toluene (25 ml) was treated drop wise with aniline (0.01 mol) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for one hour and set aside for an additional hour at room temperature for completion of the reaction. The mixture was then treated with dilute hydrochloric acid to remove unreacted aniline. The resultant N-(phenyl)succinamic acid was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. The compound was recrystallized to constant melting point from ethanol.

The N-(phenyl)succinamic acid obtained was then treated with phosphorous oxychloride and excess of p-toluidine at room temperature with constant stirring. The resultant mixture was stirred for 4 h, kept aside for additional 6 h for completion of the reaction and poured slowly into crushed ice with constant stirring. It was kept aside for a day. The resultant solid, N-(phenyl),N-(4-methylphenyl)- succinamide monohydrate, was filtered under suction, washed thoroughly with water, dilute sodium hydroxide solution and finally with water. It was recrystallized to constant melting point from a mixture of acetone and chloroform.

Colorless needles were grown in a mixture of acetone and chloroform at room temperature.