4-(4-Methylbenzenesulfonamido)benzoic acid N,N-dimethyl­formamide mono­solvate

Miao-Ling Huang; Zhi-Yang Lin

doi:10.1107/S1600536811011949

. 2011 Apr 7;67(Pt 5):o1062. doi: 10.1107/S1600536811011949

4-(4-Methylbenzenesulfonamido)benzoic acid N,N-dimethylformamide monosolvate

Miao-Ling Huang ^a,^*, Zhi-Yang Lin ^a

PMCID: PMC3089350 PMID: 21754388

Abstract

In the title compound, C₁₄H₁₃NO₄S·C₃H₇NO, the C—S—N—C torsion angle of −64.55 (17)° defines the folded conformation of the molecule. The dihedral angle between the benzene rings is 83.367 (6)°. In a crystal, molecules are linked into a chain along a axis through intermolecular N—H⋯O and O—H⋯O hydrogen bonds. There is also an intramolecular C—H⋯π interaction.

Related literature

N-protected amino acids possess an R-CONH-R′ group analogous to the structure of O-terminal peptides and proteins, see: Antolini et al. (1984 ▶); Menabue & Saladini (1988 ▶).

Experimental

Crystal data

C₁₄H₁₃NO₄S·C₃H₇NO
M _r = 364.41
Monoclinic,
a = 8.0953 (10) Å
b = 25.151 (3) Å
c = 8.8840 (11) Å
β = 98.010 (1)°
V = 1791.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.39 × 0.29 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.923, T _max = 0.949
9993 measured reflections
3336 independent reflections
2570 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.111
S = 1.04
3336 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011949/kp2315sup1.cif

e-67-o1062-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011949/kp2315Isup2.hkl

e-67-o1062-Isup2.hkl^{(163.7KB, hkl)}

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.27	2.903 (2)	131
O2—H2A⋯O5ⁱⁱ	0.82	1.79	2.598 (2)	168
C16—H16C⋯Cg1	0.96	2.98	3.576 (3)	121

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

Acknowledgments

This work was supported by the Education Department Foundation of Fujian Province of China (grant No. 2008 F5053) and the Master Construction Project of Quanzhou Normal University.

supplementary crystallographic information

Comment

N-Protected amino acids possess R-CONH-R' group analogous to the structure of O-terminal peptides and proteins (Menabue, et al., 1988, Antolini, et al., 1984). The substitution of an Ar—SO₂-group on amine addes to 4-aminobenzeoic acid the coordination donors of three types-O, N donors from carboxyl, sulfoxyl and amine respectively, which may result in different coordination modes. In this paper, we synthesized the desired ligand in N,N-dimethylformamide solvent.

The title compound contains one N-p-tolysulfonyl-4-aminobenzoic acid molecule and a solvent N, N-dimethylformamide in the asymmetric unit (Fig. 1). The molecule has a C1—N1—S1—C8 of 64.552 (2) °, and the dihedral angle between the benzene rings is 83.367 (6) °. There are intermolecular hydrogen bonds between carboxylate group oxygen atoms, nitrogen atoms and solvent oxygen atoms of the types N—H···O and O—H···O generating a chain along a axis (Figs. 2 and 3, Table 1). There are intramolecular CH···π interactions between H(16 C) and H(17B) of solvent and the centre of two aromatic rings of the title molecule(C16—H16C···C1—C2—C3—C4—C5—C6 and C17—H17B···C8—C9—C10—C11—C12—C13; the distances of H to the centre of the aromatic rings are 2.982 (3) and 3.84 (3) Å, respectively).

Experimental

A mixture of N-p-tolysulfonylchloride (1 mmol) and 4-aminobenzoic acid (1 mmol) in water(20 ml) was stirred at room temperature for 10 h. Then HCl (12 mol/L) was slowly added to the resulting solution. The mixture was stirred for 5 min and filtrated. The block colourless single crystals suitable for X-ray analysis were obtained by recrystallization from N,N-dimethylformamide. IR(KBr): 3423(s), 3198(versus), 3059(w), 2928(s), 2510(m), 1693(versus), 1635(versus), 1607(s), 1512(m), 1433(m), 1405(s), 1383(s), 1334(s), 1291(s), 1231(m), 1159(versus), 1092(s), 1021(w), 923(s), 862(m), 827(m), 765(m), 674(s), 5757(s), 547(s), 525(m), 503(w)cm^-1.