N,N-Bis(2-hy­droxy­eth­yl)-4-methyl­benzene­sulfonamide

Mushtaq, N.; Khan, I.U.; Yar, M.; Afzal, S.; Simpson, J.

doi:10.1107/S1600536812041682

Volume 68
Part 11
Page o3142
November 2012

Received 11 August 2012
Accepted 5 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.050
wR = 0.161
Data-to-parameter ratio = 19.4
Details

N,N-Bis(2-hydroxyethyl)-4-methylbenzenesulfonamide

Nafeesa Mushtaq,^a Islam Ullah Khan,^a ^* Muhammad Yar,^a Sadia Afzal ^a and Jim Simpson ^b

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin 9054, New Zealand
Correspondence e-mail: iuklodhi@yahoo.com

In the title compound C₁₁H₁₇NO₄S, an intramolecular O-HO hydrogen bond forms an S(8) ring and determines the conformation of the bis(2-hydroxyethyl) segment of the molecule, holding the two CH₂CH₂OH groups close to coplanar (r.m.s. deviation = 0.185 Å). In the crystal, O-HO hydrogen bonds link the molecules into zigzag chains along the b axis. Weaker additional C-HO and C-H [pi] contacts generate a three dimensional network, with molecules stacked along the b-axis direction.

Related literature

For pharmaceutical background to sulfonamides, see: Casini et al. (2002); Chambers & Jawetz (1998). For an alternative synthesis, see: Hori et al. (2011). For a related structure, see: Yoon et al. (2001). For standard bond lengths, see: Allen et al. (1987) and for hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₁H₁₇NO₄S
M_r = 259.32
Orthorhombic, P b c a
a = 17.9308 (5) Å
b = 7.1881 (2) Å
c = 19.8333 (6) Å
V = 2556.28 (13) Å³
Z = 8
Mo K radiation
= 0.26 mm^-1
T = 296 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
3124 measured reflections
3124 independent reflections
2343 reflections with I > 2(I)

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.161
S = 0.99
3124 reflections
161 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.45 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 benzene ring.

D-HA	D-H	HA	DA	D-HA
O4-H4OO3	0.76 (7)	1.89 (7)	2.634 (3)	166 (7)
O3-H3OO4ⁱ	0.75 (4)	1.92 (4)	2.661 (3)	172 (4)
C10-H10AO1ⁱⁱ	0.97	2.61	3.361 (3)	135
C3-H3Cg1ⁱⁱⁱ	0.93	2.78	3.522 (2)	138
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97, ORTEP-3 (Farrugia, 1997), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2181 ).

Acknowledgements

The authors acknowledge Mr Ejaz for his kind assistance with the X-ray data collection.

References

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organic compounds