N-(4-Meth­oxy­benzo­yl)-2-methyl­benzene­sulfonamide

S Sreenivasa; B S Palakshamurthy; S Madankumar; N K Lokanath; P A Suchetan

doi:10.1107/S1600536814001354

. 2014 Jan 22;70(Pt 2):o193. doi: 10.1107/S1600536814001354

N-(4-Methoxybenzoyl)-2-methylbenzenesulfonamide

S Sreenivasa ^a, B S Palakshamurthy ^b, S Madankumar ^c, N K Lokanath ^c, P A Suchetan ^d,^*

PMCID: PMC3998343 PMID: 24764904

Abstract

In the title compound, C₁₅H₁₅NO₄S, the dihedral angle between the aromatic rings is 80.81 (1)° and the dihedral angle between the planes defined by the S—N—C=O fragment and the sulfonyl benzene ring is 86.34 (1)°. In the extended structure, dimers related by a crystallographic twofold axis are connected by pairs of both N—H⋯O hydrogen bonds and C—H⋯O interactions, which generate R ₂ ²(8) and R ₂ ²(14) loops, respectively. A weak aromatic π–π stacking interaction is also observed [centroid–centroid separation = 3.7305 (3) Å].

Related literature

For related structures, see: Gowda et al. (2010 ▶); Suchetan et al. (2010a ▶,b ▶, 2011 ▶); Sreenivasa et al. (2013 ▶, 2014 ▶). graphic file with name e-70-0o193-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₅NO₄S
M _r = 305.34
Monoclinic,
a = 21.807 (2) Å
b = 7.3521 (8) Å
c = 18.602 (2) Å
β = 101.211 (3)°
V = 2925.4 (5) Å³
Z = 8
Cu Kα radiation
μ = 2.11 mm⁻¹
T = 293 K
0.38 × 0.29 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.504, T _max = 0.629
16411 measured reflections
2431 independent reflections
2174 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.122
S = 0.92
2431 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001354/hb7188sup1.cif

e-70-0o193-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001354/hb7188Isup2.hkl

e-70-0o193-Isup2.hkl^{(117.1KB, hkl)}

Click here for additional data file.^{(5.5KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814001354/hb7188Isup3.cml

CCDC reference: http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=978143

Additional supporting information: 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—H1⋯O2ⁱ	0.81 (3)	2.16 (3)	2.917 (2)	164 (3)
C13—H13⋯O2ⁱ	0.93	2.56	3.288 (3)	136

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the IOE X-ray diffractometer facility, University of Mysore, Mysore, for the data collection.

supplementary crystallographic information

1. Introduction

As a part of our continued efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Sreenivasa et al., 2014), we report here the crystal structure of the title compound (I) (Fig 1).

2. Experimental

2.1. Synthesis and crystallization

The title compound (I) was prepared by refluxing a mixture of 4-methoxybenzoic acid, 2-methylbenzenesulfonamide and phosphorous oxychloride (POCl₃) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and later dried (Melting point: 447 K).

Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methanolic solution at room temperature.

2.2. Refinement

The H atom of the NH group was located in a difference map and later refined freely. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom).

3. Results and discussion

In I, the dihedral angle between the two aromatic rings is 80.81 (1)°. Compared to this, the dihedral angle is 73.9 (1)° in N-(benzoyl)-2-methylbenzenesulfonamide (II, Suchetan et al., 2010a), 89.4 (1)° and 82.4 (1)° respectively in the two molecules in the asymmetric unit of N-(4-chlorobenzoyl)-2-methylbenzenesulfonamide (III, Suchetan et al., 2010b), 88.1 (1)° and 83.5 (1)° respectively in the two molecules in the asymmetric unit of N-(4-methylbenzoyl)-2-methylbenzenesulfonamide (IV, Gowda et al., 2010) and 83.8 (2)° in N-(4-nitrobenzoyl)-2-methylbenzenesulfonamide (V, Suchetan et al., 2011). This shows that introducing a substituent into the para position of the benzoyl ring of II correlates with a increase of the dihedral angle between the aromatic rings. In contrast to this, the dihedral angle is small in N-(4-methoxy-benzoyl)-benzenesulfonamide (VI, Sreenivasa et al., 2014) and N-(4-methoxybenzoyl)-4-methylbenzenesulfonamide (VII, Sreenivasa et al., 2013), the dihedral angle being respectively 69.81 (1)° and 78.62 (16)° in VI and VII. Further, the molecule is twisted at the S atom, the dihedral angle between the planes defined by the S—N—C=O segment in the central chain and the sulfonyl benzene ring being 86.34 (1)°.

The supramolecular architecture of I is built in three stages. In the first stage, the molecules are linked into dimers by a crystallographic twofold axis through strong N1—H1···O2 hydrogen bonds, thus generating R₂²(8) rings (Figure 2). These dimers in the second stage are linked through an additional C13—H13···O2 interaction (Figure 2) forming R₂²(14) ring motif. In the third stage, π(methylphenyl) ···π(methylphenyl) interactions stabilize the structure, Cg(methylphenyl) ···Cg(methylphenyl) distance being 3.7305 (3)Å (Figure 3). The geometries and symmetry operations of various interactions are shown in Table 1.