4-Chloro-N-(2,6-dimethyl­phen­yl)benzene­sulfonamide

Shakuntala, K.; Foro, S.; Gowda, B.T.

doi:10.1107/S160053681101717X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1401

doi:10.1107/S160053681101717X

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4-Chloro-N-(2,6-dimethylphenyl)benzenesulfonamide

K. Shakuntala,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 4 May 2011; accepted 6 May 2011; online 14 May 2011)

In the title compound, C₁₄H₁₄ClNO₂S, the amido H atom orients itself away from both the ortho-methyl groups in the adjacent aromatic ring. The molecule is twisted at the S atom with an C—SO₂—NH—C torsion angle of −69.9 (2)°. The two aromatic rings are tilted relative to each other by 31.9 (1)°. In the crystal, the molecules are packed into zigzag chains along the b axis via intermolecular N—H⋯O hydrogen bonds.

Related literature

For hydrogen-bonding modes of sulfonamides, see; Adsmond & Grant (2001 ). For our study of the effect of substituents on the structures of N-(aryl)methanesulfonamides, see: Gowda et al. (2007 ), on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2008 ); Shakuntala et al. (2011 ) and on the oxidative strengths of N-chloro,N-arylsulfonamides, see: Gowda & Kumar (2003 ).

Experimental

Crystal data

C₁₄H₁₄ClNO₂S
M_r = 295.77
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.3816 (4) Å
b = 10.2916 (7) Å
c = 18.312 (1) Å
V = 1391.13 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 293 K
0.40 × 0.28 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.850, T_max = 0.906
5356 measured reflections
2767 independent reflections
2255 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.079
S = 1.02
2767 reflections
177 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1113 Friedel pairs
Flack parameter: 0.43 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.82 (2)	2.28 (2)	3.083 (3)	166 (3)
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101717X/bq2299sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101717X/bq2299Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681101717X/bq2299Isup3.cml

checkCIF report

Comment top

The sulfonamide moieties are the constituents of many biologically important compounds. The hydrogen bonding preferences of sulfonamides has been investigated (Adsmond & Grant, 2001). As a part of studying the substituent effects on the structures and other aspects of this class of compounds (Gowda et al., 2003, 2007, 2008; Shakuntala et al., 2011), in the present work, the crystal structure of 4-chloro-N-(2,6-dimethylphenyl)-benzenesulfonamide (I) has been determined (Fig.1). In the structure, the amido H atom orients itself away from both the ortho-methyl groups in the adjacent aromatic ring. The molecule is twisted at the S atom with the C—SO₂—NH—C torsion angle of -69.9 (2)°, compared to the values of -53.8 (3)° (molecule 1) and -63.4 (3)° (molecule 2) in 4-chloro-N-(phenyl)-benzenesulfonamide (II) (Shakuntala et al., 2011) and -78.7 (2)° in N-(2,6-dimethylphenyl)-benzenesulfonamide (III) (Gowda et al., 2008)

The sulfonyl and anilino benzene rings in (I) are tilted relative to each other by 31.9 (1)°, compared to the values of 69.1 (1)° in molecule 1 and 82.6 (1)° in molecule 2 of (II), and 44.9 (1)° in (III).

The packing of molecules in (I) into zigzag chains through N—H···O(S) hydrogen bonding (Table 1) is shown in Fig.2.

Related literature top

For hydrogen bonding modes of sulfonamides, see; Adsmond & Grant (2001). For our study of the effect of substituents on the structures of N-(aryl)methanesulfonamides, see: Gowda et al. (2007), on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2008); Shakuntala et al. (2011) and on the oxidative strengths of N-chloro,N-arylsulfonamides, see: Gowda & Kumar (2003).

Experimental top

The solution of chlorobenzene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 4-chlorobenzenesulfonylchloride was treated with 2,6-dimethylaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant 4-chloro-N-(2,6-dimethylphenyl)-benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The compound was characterized by recording its infrared and NMR spectra.

Prism like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

4-Chloro-N-(2,6-dimethylphenyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₄ClNO₂S	F(000) = 616
M_r = 295.77	D_x = 1.412 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1775 reflections
a = 7.3816 (4) Å	θ = 2.8–28.0°
b = 10.2916 (7) Å	µ = 0.42 mm⁻¹
c = 18.312 (1) Å	T = 293 K
V = 1391.13 (14) Å³	Prism, colourless
Z = 4	0.40 × 0.28 × 0.24 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2767 independent reflections
Radiation source: fine-focus sealed tube	2255 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→6
T_min = 0.850, T_max = 0.906	k = −12→10
5356 measured reflections	l = −22→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0326P)² + 0.3144P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2767 reflections	Δρ_max = 0.19 e Å⁻³
177 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1113 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.43 (7)

Crystal data top

C₁₄H₁₄ClNO₂S	V = 1391.13 (14) Å³
M_r = 295.77	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.3816 (4) Å	µ = 0.42 mm⁻¹
b = 10.2916 (7) Å	T = 293 K
c = 18.312 (1) Å	0.40 × 0.28 × 0.24 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2767 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2255 reflections with I > 2σ(I)
T_min = 0.850, T_max = 0.906	R_int = 0.022
5356 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	Δρ_max = 0.19 e Å⁻³
S = 1.02	Δρ_min = −0.25 e Å⁻³
2767 reflections	Absolute structure: Flack (1983), 1113 Friedel pairs
177 parameters	Absolute structure parameter: 0.43 (7)
1 restraint

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.42735 (14)	0.03948 (8)	−0.04544 (5)	0.0851 (3)
S1	0.96404 (8)	0.20494 (6)	0.19969 (4)	0.04077 (16)
O1	0.9231 (3)	0.33512 (15)	0.22176 (9)	0.0502 (5)
O2	1.1425 (2)	0.1712 (2)	0.17729 (11)	0.0606 (6)
N1	0.9167 (3)	0.11125 (19)	0.26858 (12)	0.0389 (5)
H1N	0.950 (3)	0.0356 (17)	0.2645 (14)	0.047*
C1	0.8156 (3)	0.1660 (2)	0.12743 (13)	0.0375 (6)
C2	0.8780 (4)	0.0962 (2)	0.06798 (14)	0.0479 (7)
H2	1.0000	0.0745	0.0642	0.057*
C3	0.7573 (4)	0.0591 (3)	0.01437 (15)	0.0568 (8)
H3	0.7974	0.0119	−0.0258	0.068*
C4	0.5788 (4)	0.0917 (3)	0.02047 (14)	0.0513 (7)
C5	0.5165 (4)	0.1648 (3)	0.07828 (15)	0.0524 (7)
H5	0.3949	0.1880	0.0811	0.063*
C6	0.6357 (3)	0.2032 (3)	0.13178 (14)	0.0450 (6)
H6	0.5958	0.2539	0.1706	0.054*
C7	0.7516 (3)	0.1254 (2)	0.30961 (13)	0.0357 (5)
C8	0.6035 (3)	0.0460 (2)	0.29430 (14)	0.0424 (6)
C9	0.4451 (4)	0.0670 (3)	0.33397 (15)	0.0560 (7)
H9	0.3433	0.0166	0.3244	0.067*
C10	0.4376 (4)	0.1614 (3)	0.38707 (17)	0.0620 (8)
H10	0.3302	0.1752	0.4124	0.074*
C11	0.5853 (4)	0.2345 (3)	0.40283 (14)	0.0555 (8)
H11	0.5782	0.2965	0.4397	0.067*
C12	0.7464 (4)	0.2189 (3)	0.36519 (13)	0.0433 (6)
C13	0.6103 (4)	−0.0616 (3)	0.23877 (15)	0.0573 (7)
H13A	0.6806	−0.0340	0.1975	0.069*
H13B	0.4896	−0.0823	0.2232	0.069*
H13C	0.6652	−0.1371	0.2602	0.069*
C14	0.9069 (4)	0.2998 (3)	0.38620 (16)	0.0642 (8)
H14A	1.0162	0.2550	0.3730	0.077*
H14B	0.9055	0.3145	0.4380	0.077*
H14C	0.9017	0.3816	0.3611	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1151 (8)	0.0671 (5)	0.0730 (6)	−0.0104 (5)	−0.0493 (5)	0.0049 (4)
S1	0.0373 (3)	0.0394 (3)	0.0457 (3)	−0.0063 (3)	0.0044 (3)	−0.0015 (3)
O1	0.0686 (12)	0.0340 (9)	0.0480 (10)	−0.0116 (9)	0.0022 (9)	0.0000 (8)
O2	0.0365 (10)	0.0769 (15)	0.0684 (13)	−0.0049 (9)	0.0078 (8)	−0.0039 (11)
N1	0.0376 (12)	0.0320 (11)	0.0470 (12)	0.0027 (9)	0.0007 (9)	0.0018 (10)
C1	0.0416 (14)	0.0321 (13)	0.0389 (13)	−0.0015 (11)	0.0030 (11)	0.0013 (11)
C2	0.0529 (16)	0.0410 (15)	0.0498 (16)	0.0081 (12)	0.0069 (13)	−0.0040 (13)
C3	0.084 (2)	0.0459 (17)	0.0407 (15)	0.0074 (17)	0.0016 (15)	−0.0071 (13)
C4	0.067 (2)	0.0398 (15)	0.0468 (16)	−0.0057 (14)	−0.0123 (14)	0.0078 (13)
C5	0.0452 (15)	0.0573 (17)	0.0548 (16)	0.0013 (13)	−0.0048 (13)	0.0073 (14)
C6	0.0449 (15)	0.0453 (15)	0.0446 (14)	0.0040 (13)	0.0062 (12)	−0.0026 (13)
C7	0.0363 (12)	0.0346 (13)	0.0360 (13)	−0.0003 (10)	−0.0034 (10)	0.0064 (11)
C8	0.0429 (13)	0.0386 (14)	0.0456 (14)	−0.0053 (11)	−0.0042 (12)	0.0092 (12)
C9	0.0406 (15)	0.0624 (19)	0.0651 (17)	−0.0106 (15)	−0.0001 (14)	0.0153 (16)
C10	0.0554 (18)	0.0652 (19)	0.0655 (19)	0.0109 (16)	0.0184 (15)	0.0144 (16)
C11	0.075 (2)	0.0508 (17)	0.0405 (15)	0.0094 (15)	0.0100 (14)	0.0007 (13)
C12	0.0569 (16)	0.0379 (14)	0.0353 (13)	−0.0015 (13)	−0.0050 (12)	0.0054 (11)
C13	0.0647 (18)	0.0464 (17)	0.0607 (17)	−0.0199 (14)	−0.0066 (15)	−0.0008 (14)
C14	0.080 (2)	0.0604 (19)	0.0521 (16)	−0.0142 (18)	−0.0114 (15)	−0.0103 (16)

Geometric parameters (Å, º) top

Cl1—C4	1.731 (3)	C7—C8	1.393 (3)
S1—O2	1.4228 (18)	C7—C12	1.401 (3)
S1—O1	1.4316 (17)	C8—C9	1.393 (4)
S1—N1	1.626 (2)	C8—C13	1.504 (3)
S1—C1	1.764 (2)	C9—C10	1.375 (4)
N1—C7	1.440 (3)	C9—H9	0.9300
N1—H1N	0.818 (16)	C10—C11	1.356 (4)
C1—C2	1.383 (3)	C10—H10	0.9300
C1—C6	1.385 (3)	C11—C12	1.383 (4)
C2—C3	1.380 (4)	C11—H11	0.9300
C2—H2	0.9300	C12—C14	1.498 (4)
C3—C4	1.364 (4)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.378 (4)	C13—H13C	0.9600
C5—C6	1.375 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600

O2—S1—O1	120.37 (12)	C12—C7—N1	118.2 (2)
O2—S1—N1	106.12 (12)	C7—C8—C9	117.5 (2)
O1—S1—N1	106.90 (10)	C7—C8—C13	122.8 (2)
O2—S1—C1	107.66 (12)	C9—C8—C13	119.7 (2)
O1—S1—C1	107.05 (11)	C10—C9—C8	120.8 (3)
N1—S1—C1	108.29 (11)	C10—C9—H9	119.6
C7—N1—S1	121.78 (16)	C8—C9—H9	119.6
C7—N1—H1N	113.2 (19)	C11—C10—C9	120.7 (3)
S1—N1—H1N	115.5 (19)	C11—C10—H10	119.7
C2—C1—C6	120.6 (2)	C9—C10—H10	119.7
C2—C1—S1	120.11 (19)	C10—C11—C12	121.4 (3)
C6—C1—S1	119.31 (19)	C10—C11—H11	119.3
C3—C2—C1	119.3 (3)	C12—C11—H11	119.3
C3—C2—H2	120.4	C11—C12—C7	117.7 (2)
C1—C2—H2	120.4	C11—C12—C14	119.1 (2)
C4—C3—C2	119.8 (3)	C7—C12—C14	123.1 (2)
C4—C3—H3	120.1	C8—C13—H13A	109.5
C2—C3—H3	120.1	C8—C13—H13B	109.5
C3—C4—C5	121.3 (3)	H13A—C13—H13B	109.5
C3—C4—Cl1	119.4 (2)	C8—C13—H13C	109.5
C5—C4—Cl1	119.3 (2)	H13A—C13—H13C	109.5
C6—C5—C4	119.4 (3)	H13B—C13—H13C	109.5
C6—C5—H5	120.3	C12—C14—H14A	109.5
C4—C5—H5	120.3	C12—C14—H14B	109.5
C5—C6—C1	119.6 (2)	H14A—C14—H14B	109.5
C5—C6—H6	120.2	C12—C14—H14C	109.5
C1—C6—H6	120.2	H14A—C14—H14C	109.5
C8—C7—C12	121.8 (2)	H14B—C14—H14C	109.5
C8—C7—N1	120.0 (2)

O2—S1—N1—C7	174.71 (18)	S1—C1—C6—C5	−175.2 (2)
O1—S1—N1—C7	45.1 (2)	S1—N1—C7—C8	97.6 (2)
C1—S1—N1—C7	−69.9 (2)	S1—N1—C7—C12	−83.4 (3)
O2—S1—C1—C2	9.0 (2)	C12—C7—C8—C9	3.2 (4)
O1—S1—C1—C2	139.75 (19)	N1—C7—C8—C9	−177.8 (2)
N1—S1—C1—C2	−105.3 (2)	C12—C7—C8—C13	−175.3 (2)
O2—S1—C1—C6	−172.5 (2)	N1—C7—C8—C13	3.7 (4)
O1—S1—C1—C6	−41.8 (2)	C7—C8—C9—C10	−1.1 (4)
N1—S1—C1—C6	73.1 (2)	C13—C8—C9—C10	177.4 (2)
C6—C1—C2—C3	−2.8 (4)	C8—C9—C10—C11	−1.2 (4)
S1—C1—C2—C3	175.7 (2)	C9—C10—C11—C12	1.5 (4)
C1—C2—C3—C4	0.2 (4)	C10—C11—C12—C7	0.5 (4)
C2—C3—C4—C5	2.0 (4)	C10—C11—C12—C14	−178.4 (3)
C2—C3—C4—Cl1	−177.7 (2)	C8—C7—C12—C11	−2.9 (4)
C3—C4—C5—C6	−1.5 (4)	N1—C7—C12—C11	178.1 (2)
Cl1—C4—C5—C6	178.1 (2)	C8—C7—C12—C14	175.9 (2)
C4—C5—C6—C1	−1.1 (4)	N1—C7—C12—C14	−3.1 (4)
C2—C1—C6—C5	3.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.82 (2)	2.28 (2)	3.083 (3)	166 (3)

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄ClNO₂S
M_r	295.77
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	7.3816 (4), 10.2916 (7), 18.312 (1)
V (Å³)	1391.13 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.40 × 0.28 × 0.24

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.850, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	5356, 2767, 2255
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.079, 1.02
No. of reflections	2767
No. of parameters	177
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.25
Absolute structure	Flack (1983), 1113 Friedel pairs
Absolute structure parameter	0.43 (7)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.818 (16)	2.282 (17)	3.083 (3)	166 (3)

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Acknowledgements

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

References

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058–2077. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1691. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T. & Kumar, B. H. A. (2003). Oxid. Commun. 26, 403–425. CAS Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Shakuntala, K., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o1252. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar