N-(3,5-Dichloro­phen­yl)-2-nitro­benzene­sulfonamide

Chaithanya, U.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536812048283

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3482

doi:10.1107/S1600536812048283

Open

access

N-(3,5-Dichlorophenyl)-2-nitrobenzenesulfonamide

U. Chaithanya,^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 21 November 2012; accepted 25 November 2012; online 30 November 2012)

In the title compound, C₁₂H₈Cl₂N₂O₄S, the C—S—N—C torsion angle is 49.34 (18)° and the dihedral angle between the benzene rings is 71.92 (10)°. The amide H atom exhibits bifurcated hydrogen bonding. The N—H bond is syn to the ortho-nitro group enabling the formation of an S(7) loop. In the crystal, pairs of N—H⋯O(S) hydrogen bonds link the molecules into inversion dimers via R₂²(8) rings.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994 ); Shahwar et al. (2012 ), of N-arylsulfonamides, see: Chaithanya et al. (2012 ) and of N-chloroarylsulfonamides, see: Shetty & Gowda (2004 ). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001 ).

Experimental

Crystal data

C₁₂H₈Cl₂N₂O₄S
M_r = 347.16
Triclinic, $[P \overline 1]$
a = 8.2823 (8) Å
b = 8.3436 (9) Å
c = 10.670 (1) Å
α = 76.730 (8)°
β = 89.298 (9)°
γ = 86.875 (9)°
V = 716.59 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.61 mm⁻¹
T = 293 K
0.44 × 0.40 × 0.28 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 = 0.774, T_max = 0.847
4766 measured reflections
2925 independent reflections
2600 reflections with I > 2σ(I)
R_int = 0.009

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.092
S = 1.04
2925 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.85 (2)	2.23 (2)	3.052 (2)	162 (2)
N1—H1N⋯O3	0.85 (2)	2.44 (2)	2.940 (2)	118 (2)
Symmetry code: (i) -x, -y, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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/S1600536812048283/tk5173sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812048283/tk5173Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812048283/tk5173Isup3.cml

checkCIF report

Comment top

As a part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda & Weiss, 1994; Shahwar et al., 2012); N-arylsulfonamides (Chaithanya et al., 2012); and N-chloroarylsulfonamides (Shetty & Gowda, 2004), in the present work, the crystal structure of N-(3,5-dichlorophenyl)-2-nitrobenzenesulfonamide (I) has been determined (Fig. 1).

The conformation of the N—C bond in the —SO₂—NH—C segment has gauche torsions with respect to the S═O bonds (Fig. 1), similar to that observed in N-(3,5-dimethylphenyl)-2-nitrobenzenesulfonamide (II) (Chaithanya et al., 2012). Further, the conformation of the N—H bond in the —SO₂—NH— segment is syn to the ortho- nitro group in the sulfonyl benzene ring. The molecule is twisted at the S—N bond with the torsional angle of 49.34 (18)°, compared to the values of 44.24 (26) and -49.34 (25)° in the two independent molecules of (II).

The dihedral angle between the sulfonyl and the aniline rings in (I) is 71.92 (10)°, compared to the values of 71.53 (7)° and 72.11 (7)° in the two molecules of (II).

The amide H-atom shows bifurcated intramolecular H-bonding with the O-atom of the ortho-nitro group in the sulfonyl benzene ring, generating S(7) motifs, and the intermolecular H-bonding with the sulfonyl oxygen atom of a symmetry related molecule, generating R²₂(8) motifs (Adsmond et al., 2001). The latter (Table 1) link the molecules into inversion dimers. Part of the crystal structure is shown in Fig. 2.

Related literature top

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994); Shahwar et al. (2012), of N-arylsulfonamides, see: Chaithanya et al. (2012) and of N-chloroarylsulfonamides, see: Shetty & Gowda (2004). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001),

Experimental top

The title compound was prepared by treating 2-nitrobenzenesulfonylchloride with 3,5-dichloroaniline in a stoichiometric ratio and boiling the reaction mixture for 15 minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid, N-(3,5-dichlorophenyl)-2-nitrobenzenesulfonamide, was filtered under suction and washed thoroughly with cold water and dilute HCl to remove the excess sulfonylchloride and aniline, respectively. It was then recrystallized to constant melting point from dilute ethanol.

Prism-like colourless crystals of the title compound used in X-ray diffraction studies were grown from its ethanolic solution by slow evaporation of the solvent at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (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 the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level. The dashed line indicates an intramolecular N—H···O hydrogen bond.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

N-(3,5-Dichlorophenyl)-2-nitrobenzenesulfonamide top

Crystal data top

C₁₂H₈Cl₂N₂O₄S	Z = 2
M_r = 347.16	F(000) = 352
Triclinic, P1	D_x = 1.609 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2823 (8) Å	Cell parameters from 3256 reflections
b = 8.3436 (9) Å	θ = 3.1–27.7°
c = 10.670 (1) Å	µ = 0.61 mm⁻¹
α = 76.730 (8)°	T = 293 K
β = 89.298 (9)°	Prism, colourless
γ = 86.875 (9)°	0.44 × 0.40 × 0.28 mm
V = 716.59 (12) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2925 independent reflections
Radiation source: fine-focus sealed tube	2600 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.009
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→10
T_min = 0.774, T_max = 0.847	k = −9→10
4766 measured reflections	l = −7→13

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0408P)² + 0.4244P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2925 reflections	Δρ_max = 0.44 e Å⁻³
194 parameters	Δρ_min = −0.49 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.100 (5)

Crystal data top

C₁₂H₈Cl₂N₂O₄S	γ = 86.875 (9)°
M_r = 347.16	V = 716.59 (12) Å³
Triclinic, P1	Z = 2
a = 8.2823 (8) Å	Mo Kα radiation
b = 8.3436 (9) Å	µ = 0.61 mm⁻¹
c = 10.670 (1) Å	T = 293 K
α = 76.730 (8)°	0.44 × 0.40 × 0.28 mm
β = 89.298 (9)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2925 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2600 reflections with I > 2σ(I)
T_min = 0.774, T_max = 0.847	R_int = 0.009
4766 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.44 e Å⁻³
2925 reflections	Δρ_min = −0.49 e Å⁻³
194 parameters

Special details top

Experimental. Absorption correction: 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
C1	0.3367 (2)	0.2350 (2)	0.37443 (17)	0.0340 (4)
C2	0.2649 (2)	0.3607 (2)	0.42524 (17)	0.0371 (4)
C3	0.3229 (3)	0.5157 (2)	0.4011 (2)	0.0459 (5)
H3	0.2729	0.5973	0.4369	0.055*
C4	0.4565 (3)	0.5488 (3)	0.3228 (2)	0.0492 (5)
H4	0.4964	0.6537	0.3046	0.059*
C5	0.5305 (2)	0.4268 (3)	0.2718 (2)	0.0498 (5)
H5	0.6207	0.4496	0.2192	0.060*
C6	0.4721 (2)	0.2700 (2)	0.29780 (19)	0.0419 (4)
H6	0.5241	0.1880	0.2636	0.050*
C7	0.0975 (2)	0.1026 (2)	0.19048 (18)	0.0380 (4)
C8	0.2129 (2)	0.0663 (3)	0.1044 (2)	0.0448 (4)
H8	0.3031	−0.0032	0.1331	0.054*
C9	0.1901 (3)	0.1361 (3)	−0.0251 (2)	0.0495 (5)
C10	0.0575 (3)	0.2374 (3)	−0.0718 (2)	0.0560 (6)
H10	0.0443	0.2824	−0.1594	0.067*
C11	−0.0553 (3)	0.2695 (3)	0.0166 (2)	0.0549 (5)
C12	−0.0370 (2)	0.2058 (3)	0.14680 (19)	0.0472 (5)
H12	−0.1136	0.2315	0.2046	0.057*
N1	0.10830 (19)	0.0311 (2)	0.32445 (15)	0.0403 (4)
H1N	0.024 (2)	0.045 (3)	0.367 (2)	0.048*
N2	0.1200 (2)	0.3345 (2)	0.50690 (17)	0.0481 (4)
O1	0.39505 (17)	−0.06691 (17)	0.36502 (15)	0.0478 (3)
O2	0.21976 (16)	−0.01250 (17)	0.54098 (13)	0.0438 (3)
O3	0.00227 (19)	0.2822 (2)	0.4655 (2)	0.0675 (5)
O4	0.1245 (3)	0.3732 (2)	0.60935 (17)	0.0764 (6)
Cl1	0.33194 (8)	0.08990 (10)	−0.13460 (6)	0.0734 (2)
Cl2	−0.22590 (10)	0.39424 (13)	−0.03893 (7)	0.0972 (3)
S1	0.27077 (5)	0.03037 (5)	0.40942 (4)	0.03530 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0303 (8)	0.0350 (9)	0.0351 (9)	−0.0007 (7)	0.0013 (7)	−0.0052 (7)
C2	0.0361 (9)	0.0384 (9)	0.0349 (9)	0.0005 (7)	0.0055 (7)	−0.0054 (7)
C3	0.0510 (11)	0.0397 (10)	0.0480 (11)	−0.0017 (8)	0.0055 (9)	−0.0121 (8)
C4	0.0502 (11)	0.0416 (10)	0.0550 (12)	−0.0117 (9)	0.0049 (9)	−0.0074 (9)
C5	0.0388 (10)	0.0546 (12)	0.0541 (12)	−0.0114 (9)	0.0127 (9)	−0.0074 (10)
C6	0.0343 (9)	0.0461 (11)	0.0452 (10)	−0.0008 (8)	0.0080 (8)	−0.0113 (8)
C7	0.0370 (9)	0.0437 (10)	0.0349 (9)	−0.0102 (8)	0.0032 (7)	−0.0104 (8)
C8	0.0386 (10)	0.0517 (11)	0.0449 (11)	−0.0060 (8)	0.0070 (8)	−0.0123 (9)
C9	0.0472 (11)	0.0633 (13)	0.0411 (11)	−0.0130 (10)	0.0143 (9)	−0.0171 (10)
C10	0.0607 (13)	0.0719 (15)	0.0347 (10)	−0.0075 (11)	0.0036 (9)	−0.0101 (10)
C11	0.0515 (12)	0.0702 (15)	0.0413 (11)	0.0051 (11)	−0.0041 (9)	−0.0105 (10)
C12	0.0415 (10)	0.0637 (13)	0.0375 (10)	0.0027 (9)	0.0026 (8)	−0.0152 (9)
N1	0.0330 (8)	0.0512 (9)	0.0356 (8)	−0.0068 (7)	0.0055 (6)	−0.0070 (7)
N2	0.0528 (10)	0.0374 (9)	0.0497 (10)	0.0056 (7)	0.0200 (8)	−0.0040 (7)
O1	0.0430 (7)	0.0395 (7)	0.0611 (9)	0.0055 (6)	0.0042 (6)	−0.0141 (6)
O2	0.0438 (7)	0.0464 (8)	0.0363 (7)	−0.0034 (6)	0.0012 (6)	0.0008 (6)
O3	0.0427 (8)	0.0656 (11)	0.0972 (14)	−0.0082 (8)	0.0266 (9)	−0.0246 (10)
O4	0.0956 (14)	0.0836 (13)	0.0489 (10)	0.0012 (11)	0.0302 (9)	−0.0156 (9)
Cl1	0.0674 (4)	0.0992 (5)	0.0540 (4)	−0.0063 (3)	0.0297 (3)	−0.0193 (3)
Cl2	0.0839 (5)	0.1405 (8)	0.0550 (4)	0.0480 (5)	−0.0145 (3)	−0.0092 (4)
S1	0.0331 (2)	0.0330 (2)	0.0379 (3)	0.00006 (16)	0.00272 (17)	−0.00480 (17)

Geometric parameters (Å, º) top

C1—C6	1.384 (2)	C8—C9	1.382 (3)
C1—C2	1.390 (3)	C8—H8	0.9300
C1—S1	1.7763 (18)	C9—C10	1.374 (3)
C2—C3	1.372 (3)	C9—Cl1	1.737 (2)
C2—N2	1.470 (2)	C10—C11	1.378 (3)
C3—C4	1.379 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.376 (3)
C4—C5	1.374 (3)	C11—Cl2	1.735 (2)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.386 (3)	N1—S1	1.6308 (16)
C5—H5	0.9300	N1—H1N	0.848 (16)
C6—H6	0.9300	N2—O4	1.210 (2)
C7—C8	1.387 (3)	N2—O3	1.217 (3)
C7—C12	1.387 (3)	O1—S1	1.4200 (14)
C7—N1	1.419 (2)	O2—S1	1.4312 (14)

C6—C1—C2	117.76 (17)	C10—C9—C8	122.82 (19)
C6—C1—S1	118.50 (14)	C10—C9—Cl1	118.30 (17)
C2—C1—S1	123.64 (13)	C8—C9—Cl1	118.86 (18)
C3—C2—C1	122.36 (17)	C9—C10—C11	117.3 (2)
C3—C2—N2	116.28 (17)	C9—C10—H10	121.3
C1—C2—N2	121.35 (16)	C11—C10—H10	121.3
C2—C3—C4	118.96 (19)	C12—C11—C10	122.3 (2)
C2—C3—H3	120.5	C12—C11—Cl2	119.11 (18)
C4—C3—H3	120.5	C10—C11—Cl2	118.64 (18)
C5—C4—C3	119.99 (19)	C11—C12—C7	118.90 (19)
C5—C4—H4	120.0	C11—C12—H12	120.6
C3—C4—H4	120.0	C7—C12—H12	120.6
C4—C5—C6	120.64 (18)	C7—N1—S1	123.42 (13)
C4—C5—H5	119.7	C7—N1—H1N	114.9 (16)
C6—C5—H5	119.7	S1—N1—H1N	111.2 (16)
C1—C6—C5	120.27 (18)	O4—N2—O3	124.45 (19)
C1—C6—H6	119.9	O4—N2—C2	117.1 (2)
C5—C6—H6	119.9	O3—N2—C2	118.40 (18)
C8—C7—C12	120.52 (18)	O1—S1—O2	119.91 (9)
C8—C7—N1	121.79 (18)	O1—S1—N1	108.52 (9)
C12—C7—N1	117.63 (17)	O2—S1—N1	105.46 (8)
C9—C8—C7	118.2 (2)	O1—S1—C1	106.10 (8)
C9—C8—H8	120.9	O2—S1—C1	108.89 (8)
C7—C8—H8	120.9	N1—S1—C1	107.41 (8)

C6—C1—C2—C3	0.5 (3)	C10—C11—C12—C7	−1.5 (4)
S1—C1—C2—C3	177.01 (15)	Cl2—C11—C12—C7	178.31 (17)
C6—C1—C2—N2	179.58 (17)	C8—C7—C12—C11	1.0 (3)
S1—C1—C2—N2	−3.9 (3)	N1—C7—C12—C11	−176.4 (2)
C1—C2—C3—C4	0.5 (3)	C8—C7—N1—S1	50.4 (2)
N2—C2—C3—C4	−178.64 (19)	C12—C7—N1—S1	−132.29 (17)
C2—C3—C4—C5	−0.8 (3)	C3—C2—N2—O4	−52.3 (3)
C3—C4—C5—C6	0.2 (3)	C1—C2—N2—O4	128.6 (2)
C2—C1—C6—C5	−1.2 (3)	C3—C2—N2—O3	124.8 (2)
S1—C1—C6—C5	−177.86 (16)	C1—C2—N2—O3	−54.3 (3)
C4—C5—C6—C1	0.9 (3)	C7—N1—S1—O1	−64.96 (18)
C12—C7—C8—C9	0.2 (3)	C7—N1—S1—O2	165.37 (15)
N1—C7—C8—C9	177.49 (18)	C7—N1—S1—C1	49.34 (18)
C7—C8—C9—C10	−1.0 (3)	C6—C1—S1—O1	9.79 (17)
C7—C8—C9—Cl1	−179.14 (15)	C2—C1—S1—O1	−166.71 (16)
C8—C9—C10—C11	0.5 (4)	C6—C1—S1—O2	140.13 (15)
Cl1—C9—C10—C11	178.63 (18)	C2—C1—S1—O2	−36.37 (18)
C9—C10—C11—C12	0.8 (4)	C6—C1—S1—N1	−106.13 (16)
C9—C10—C11—Cl2	−179.01 (19)	C2—C1—S1—N1	77.38 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.85 (2)	2.23 (2)	3.052 (2)	162 (2)
N1—H1N···O3	0.85 (2)	2.44 (2)	2.940 (2)	118 (2)

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₈Cl₂N₂O₄S
M_r	347.16
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.2823 (8), 8.3436 (9), 10.670 (1)
α, β, γ (°)	76.730 (8), 89.298 (9), 86.875 (9)
V (Å³)	716.59 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.44 × 0.40 × 0.28

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	0.774, 0.847
No. of measured, independent and observed [I > 2σ(I)] reflections	4766, 2925, 2600
R_int	0.009
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.092, 1.04
No. of reflections	2925
No. of parameters	194
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)	0.44, −0.49

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···O2ⁱ	0.848 (16)	2.234 (17)	3.052 (2)	162 (2)
N1—H1N···O3	0.848 (16)	2.44 (2)	2.940 (2)	118.1 (18)

Symmetry code: (i) −x, −y, −z+1.

Acknowledgements

UC thanks Mangalore University for the award of a research fellowship. BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.

References

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058–2077. Web of Science CrossRef PubMed CAS Google Scholar
Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2823. CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695–702. CAS Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63–72. CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar