N-(3-Chloro­phen­yl)-N′-(2-methyl­phenyl)succinamide monohydrate

B S Saraswathi; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811014942

. 2011 Apr 29;67(Pt 5):o1223. doi: 10.1107/S1600536811014942

N-(3-Chlorophenyl)-N′-(2-methylphenyl)succinamide monohydrate

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

PMCID: PMC3089173 PMID: 21754521

Abstract

In the title compound, C₁₇H₁₇ClN₂O₂·H₂O, the dihedral angles formed by the aromatic rings of the chlorobenzene and methylbenzene groups with the mean planes of the attached NH–C(O)–CH₂ fragments are 9.4 (4) and 62.9 (2)°, respectively. In the crystal, molecules are packed into layers parallel to the bc plane by O—H⋯O and N—H⋯O hydrogen-bond interactions.

Related literature

For our study on the effects of substituents on the structures of N-(aryl)amides, see: Gowda et al. (2004 ▶); Saraswathi et al. (2011a ▶,b ▶). For the oxidative strengths of N-chloro-N-arylsulfonamides, see: Gowda & Kumar (2003 ▶).

Experimental

Crystal data

C₁₇H₁₇ClN₂O₂·H₂O
M _r = 334.79
Monoclinic,
a = 14.875 (4) Å
b = 13.908 (3) Å
c = 8.088 (2) Å
β = 90.11 (2)°
V = 1673.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.24 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 = 0.900, T _max = 0.981
6273 measured reflections
3080 independent reflections
1436 reflections with I > 2σ(I)
R _int = 0.074

Refinement

R[F ² > 2σ(F ²)] = 0.115
wR(F ²) = 0.285
S = 1.14
3080 reflections
221 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.27 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/S1600536811014942/rz2582sup1.cif

e-67-o1223-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014942/rz2582Isup2.hkl

e-67-o1223-Isup2.hkl^{(151.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811014942/rz2582Isup3.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⋯O3ⁱ	0.86 (2)	2.08 (2)	2.940 (7)	175 (6)
N2—H2N⋯O2ⁱⁱ	0.86 (2)	2.25 (4)	2.991 (7)	145 (6)
O3—H31O⋯O2	0.85 (2)	2.04 (3)	2.861 (6)	163 (8)
O3—H32O⋯O1ⁱⁱⁱ	0.84 (2)	2.05 (3)	2.877 (6)	171 (9)

Open in a new tab

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 programme.

supplementary crystallographic information

Comment

The amide and sulfonamide moieties are important constituents of many biologically important compounds. As a part of studying the substituent effects on the structures and other aspects of this class of compounds (Gowda & Kumar, 2003; Gowda et al., 2004; Saraswathi et al., 2011a,b), in the present work, the structure of N-(3-chlorophenyl)-N-(2-methylphenyl)-succinamide monohydrate is reported (Fig. 1). The conformations of the N—H and C═O bonds in the C—NH—C(O)—C—C—C(O)—NH—C fragment are anti to each other and the amide O atom is anti to the H atoms attached to the adjacent C atoms. Further, the conformations of the N—H bonds in the amide fragments are anti to the meta-chloro or the ortho-methyl groups in the respective adjacent benzene rings, similar to the anti conformations observed with respect to the ortho-methyl groups in N,N'-bis(2-methylphenyl)succinamide (II; Saraswathi et al., 2011a) and the meta-chloro groups in N,N'-bis(3-chlorophenyl)-succinamide (III; Saraswathi et al., 2011b).

The dihedral angle between the 3-chlorobenzene ring and the adjacent NH—C(O)—CH₂ group is 9.4 (4)° and that between the 2-methylbenzene ring and the adjacent NH—C(O)—CH₂ group is 62.9 (2)°, compared to the values of 62.1 (2)° for that between the benzene ring and the NH—C(O)—CH₂ group in the two halves of (II), and 32.8 (1)° in (III)

The torsion angles C1—N1—C7—C8 and C11—N2—C10—C9 are -173.0 (6)° and -177.9 (6)°, in contrast to the value of 69.5 (7)° for the torsion angle C7—C8—C9—C10.

In the crystal packing, molecules are linked by N1—H1N···O3, N2—H2N···O2, O3—H31O···O2 and O3—H32O···O1 hydrogen bonds (Table 1; Fig. 2) to form layers parallel to the bc plane.

Experimental

Succinic anhydride (0.01 mol) in toluene (25 ml) was treated drop wise with o-toluidine (0.01 mol) 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 o-toluidine. The resultant solid N-(2-methylphenyl)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 purity of the compound was checked by elemental analysis and characterized by its infrared and NMR spectra.

The N-(2-methylphenyl)succinamic acid obtained was then treated with phosphorous oxychloride and excess of 3-chloroaniline 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-(3-chlorophenyl)-N'-(2-methylphenyl)succinamide monohydrate was filtered under suction, washed thoroughly with water, with a dilute sodium hydroxide solution and finally with water. It was recrystallized to constant melting point from an acetone/chloroform (1:1 v/v) solution. The purity of the compound was checked by elemental analysis, and characterized by its infrared and NMR spectra. Needle-like colourless single crystals used for the X-ray diffraction studies were grown by slow evaporation of an acetone/chloroform (1:1 v/v) solution at room temperature.