N-(2-Methyl­phen­yl)-2-nitro­benzene­sulfonamide

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

doi:10.1107/S160053681203423X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2649

doi:10.1107/S160053681203423X

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N-(2-Methylphenyl)-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 31 July 2012; accepted 1 August 2012; online 4 August 2012)

In the title compound, C₁₃H₁₂N₂O₄S, the dihedral angle between the benzene rings is 53.44 (14)°. The amide H atom exhibits bifurcated hydrogen bonding: an intramolecular N—H⋯O hydrogen bond generates an S(7) motif while in the crystal, N—H⋯O(S) hydrogen bonds link the molecules into zigzag C(4) chains along the c axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al. (2011 ); Bowes et al. (2003 ); Gowda & Weiss (1994 ); Saeed et al. (2010 ); Shahwar et al. (2012 ), of N-arylsulfonamides, see: Chaithanya et al. (2012 ); Gowda et al. (2002 ) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004 ); Shetty & Gowda (2004 ). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001 ); Allen et al. (1998 ); Bernstein et al. (1995 ); Etter (1990 ).

Experimental

Crystal data

C₁₃H₁₂N₂O₄S
M_r = 292.31
Monoclinic, P 2₁ /c
a = 9.2409 (7) Å
b = 15.1531 (9) Å
c = 10.5376 (8) Å
β = 107.775 (8)°
V = 1405.13 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.30 × 0.28 × 0.14 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 = 0.930, T_max = 0.967
5234 measured reflections
2538 independent reflections
2020 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.114
S = 1.21
2538 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.84 (2)	2.16 (2)	2.897 (3)	146 (3)
N1—H1N⋯O3	0.84 (2)	2.57 (3)	3.132 (4)	125 (3)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis 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/S160053681203423X/bt5990sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681203423X/bt5990Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681203423X/bt5990Isup3.cml

checkCIF report

Comment top

As part of studying the substituent effects on the structures and other aspects of N-(aryl)-amides (Alkan et al., 2011; Bowes et al., 2003; Gowda et al., 1994; Saeed et al., 2010; Shahwar et al., 2012); N-arylsulfonamides (Chaithanya et al., 2012; Gowda et al., 2002) and N-chloroarylsulfonamides (Gowda & Shetty, 2004; Shetty & Gowda, 2004), in the present work, the crystal structure of N-(2-methylphenyl)-2-nitrobenzenesulfonamide has been determined (Fig. 1).

The conformation of the N—H bond in the —SO₂—NH— segment is syn to both the ortho-nitro group in the sulfonyl benzene ring and ortho-methyl group in the anilino ring. similar to that observed in N-(2-chlorophenyl)-2-nitrobenzenesulfonamide (I) (Chaithanya et al., 2012). The molecule is twisted at the S—N bond with the torsional angle of 73.90 (26)°, compared to the value of 74.97 (20)° in (I).

The dihedral angle between the sulfonyl and the anilino rings is 53.44 (14)°, compared to the value of 54.97 (11)° in (I).

The amide H-atom showed 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 the other molecule, generating C(4) motifs (Adsmond et al., 2001; Allen et al., 1998; Bernstein et al., 1995; Etter, 1990).

In the crystal, the intermolecular N–H···O (S) hydrogen bonds (Table 1) link the molecules into zigzag chains. 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: Alkan et al. (2011); Bowes et al. (2003); Gowda et al. (1994); Saeed et al. (2010); Shahwar et al. (2012), of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2002) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004); Shetty & Gowda (2004). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001); Allen et al. (1998); Bernstein et al. (1995); Etter (1990).

Experimental top

The title compound was prepared by treating 2-nitrobenzenesulfonylchloride with 2-methylaniline in the 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-(2-methylphenyl)-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 (138° C) from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Prism like colourless single crystals of the title compound used in X-ray diffraction studies were grown in 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.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

N-(2-Methylphenyl)-2-nitrobenzenesulfonamide top

Crystal data top

C₁₃H₁₂N₂O₄S	F(000) = 608
M_r = 292.31	D_x = 1.382 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2693 reflections
a = 9.2409 (7) Å	θ = 2.4–27.9°
b = 15.1531 (9) Å	µ = 0.24 mm⁻¹
c = 10.5376 (8) Å	T = 293 K
β = 107.775 (8)°	Prism, colourless
V = 1405.13 (17) Å³	0.30 × 0.28 × 0.14 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2538 independent reflections
Radiation source: fine-focus sealed tube	2020 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Rotation method data acquisition using ω scans	θ_max = 25.3°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→10
T_min = 0.930, T_max = 0.967	k = −13→18
5234 measured reflections	l = −12→7

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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0183P)² + 1.6828P] where P = (F_o² + 2F_c²)/3
S = 1.21	(Δ/σ)_max < 0.001
2538 reflections	Δρ_max = 0.33 e Å⁻³
186 parameters	Δρ_min = −0.36 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: 0.0218 (11)

Crystal data top

C₁₃H₁₂N₂O₄S	V = 1405.13 (17) Å³
M_r = 292.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2409 (7) Å	µ = 0.24 mm⁻¹
b = 15.1531 (9) Å	T = 293 K
c = 10.5376 (8) Å	0.30 × 0.28 × 0.14 mm
β = 107.775 (8)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2538 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2020 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.967	R_int = 0.020
5234 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	1 restraint
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.21	Δρ_max = 0.33 e Å⁻³
2538 reflections	Δρ_min = −0.36 e Å⁻³
186 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	0.8680 (4)	0.8982 (2)	0.1561 (3)	0.0402 (7)
C2	0.9459 (4)	0.9674 (2)	0.2349 (3)	0.0469 (8)
C3	0.9184 (5)	1.0536 (3)	0.1983 (4)	0.0751 (12)
H3	0.9734	1.0984	0.2519	0.090*
C4	0.8083 (7)	1.0730 (3)	0.0814 (5)	0.1027 (18)
H4	0.7866	1.1315	0.0561	0.123*
C5	0.7297 (6)	1.0062 (3)	0.0013 (5)	0.0987 (17)
H5	0.6558	1.0200	−0.0784	0.118*
C6	0.7592 (5)	0.9189 (3)	0.0379 (3)	0.0643 (11)
H6	0.7058	0.8743	−0.0172	0.077*
C7	0.6429 (3)	0.7470 (2)	0.2485 (3)	0.0355 (7)
C8	0.5448 (3)	0.8102 (2)	0.2718 (3)	0.0412 (7)
C9	0.3903 (4)	0.7914 (3)	0.2266 (4)	0.0575 (9)
H9	0.3219	0.8314	0.2430	0.069*
C10	0.3359 (4)	0.7149 (3)	0.1580 (4)	0.0670 (11)
H10	0.2318	0.7048	0.1266	0.080*
C11	0.4352 (4)	0.6535 (3)	0.1360 (4)	0.0617 (10)
H11	0.3984	0.6018	0.0899	0.074*
C12	0.5896 (4)	0.6689 (2)	0.1826 (3)	0.0478 (8)
H12	0.6575	0.6271	0.1699	0.057*
C13	0.5994 (4)	0.8958 (2)	0.3419 (3)	0.0534 (9)
H13A	0.6317	0.9343	0.2835	0.080*
H13B	0.6832	0.8846	0.4204	0.080*
H13C	0.5183	0.9231	0.3667	0.080*
N1	0.8048 (3)	0.75960 (17)	0.2967 (2)	0.0361 (6)
H1N	0.842 (3)	0.777 (2)	0.376 (2)	0.043*
N2	1.0601 (3)	0.95139 (19)	0.3651 (3)	0.0525 (7)
O1	0.8457 (3)	0.73616 (14)	0.0804 (2)	0.0524 (6)
O2	1.0594 (2)	0.77794 (15)	0.2763 (2)	0.0525 (6)
O3	1.0199 (3)	0.91081 (18)	0.4480 (2)	0.0641 (7)
O4	1.1859 (3)	0.9820 (2)	0.3820 (3)	0.0883 (10)
S1	0.90370 (9)	0.78584 (5)	0.20049 (7)	0.0364 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0524 (19)	0.0362 (18)	0.0334 (16)	0.0002 (14)	0.0152 (14)	0.0012 (13)
C2	0.057 (2)	0.0376 (19)	0.0454 (19)	−0.0006 (16)	0.0145 (17)	0.0021 (15)
C3	0.101 (3)	0.039 (2)	0.072 (3)	−0.005 (2)	0.007 (2)	0.005 (2)
C4	0.151 (5)	0.044 (3)	0.088 (4)	0.010 (3)	−0.001 (3)	0.021 (3)
C5	0.134 (5)	0.070 (3)	0.061 (3)	0.013 (3)	−0.017 (3)	0.019 (2)
C6	0.085 (3)	0.054 (2)	0.042 (2)	0.000 (2)	0.002 (2)	0.0026 (18)
C7	0.0391 (16)	0.0386 (17)	0.0306 (14)	0.0002 (13)	0.0132 (13)	0.0026 (13)
C8	0.0439 (18)	0.0427 (18)	0.0410 (17)	0.0008 (14)	0.0188 (15)	0.0015 (14)
C9	0.045 (2)	0.062 (2)	0.070 (2)	0.0026 (18)	0.0233 (18)	0.000 (2)
C10	0.043 (2)	0.075 (3)	0.084 (3)	−0.014 (2)	0.020 (2)	−0.007 (2)
C11	0.060 (2)	0.053 (2)	0.071 (3)	−0.0206 (19)	0.019 (2)	−0.014 (2)
C12	0.053 (2)	0.042 (2)	0.051 (2)	−0.0049 (16)	0.0201 (17)	−0.0056 (16)
C13	0.058 (2)	0.048 (2)	0.059 (2)	0.0070 (17)	0.0241 (18)	−0.0073 (17)
N1	0.0383 (14)	0.0438 (15)	0.0264 (12)	−0.0010 (11)	0.0099 (11)	−0.0014 (11)
N2	0.0560 (19)	0.0401 (16)	0.0549 (18)	−0.0031 (14)	0.0073 (15)	−0.0079 (14)
O1	0.0771 (16)	0.0457 (14)	0.0438 (12)	−0.0102 (12)	0.0323 (12)	−0.0128 (10)
O2	0.0374 (12)	0.0496 (14)	0.0725 (16)	0.0072 (10)	0.0195 (11)	−0.0014 (12)
O3	0.0784 (18)	0.0623 (17)	0.0461 (14)	−0.0001 (14)	0.0108 (13)	−0.0009 (13)
O4	0.0593 (18)	0.080 (2)	0.109 (2)	−0.0248 (16)	0.0016 (17)	−0.0003 (18)
S1	0.0422 (4)	0.0335 (4)	0.0377 (4)	0.0002 (3)	0.0183 (3)	−0.0046 (3)

Geometric parameters (Å, º) top

C1—C6	1.376 (4)	C9—C10	1.376 (5)
C1—C2	1.393 (4)	C9—H9	0.9300
C1—S1	1.770 (3)	C10—C11	1.375 (5)
C2—C3	1.363 (5)	C10—H10	0.9300
C2—N2	1.473 (4)	C11—C12	1.380 (5)
C3—C4	1.369 (6)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.374 (6)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C6	1.382 (6)	C13—H13C	0.9600
C5—H5	0.9300	N1—S1	1.609 (2)
C6—H6	0.9300	N1—H1N	0.841 (17)
C7—C12	1.384 (4)	N2—O4	1.213 (4)
C7—C8	1.391 (4)	N2—O3	1.215 (4)
C7—N1	1.438 (4)	O1—S1	1.429 (2)
C8—C9	1.390 (4)	O2—S1	1.422 (2)
C8—C13	1.501 (4)

C6—C1—C2	118.0 (3)	C11—C10—C9	120.2 (3)
C6—C1—S1	119.0 (3)	C11—C10—H10	119.9
C2—C1—S1	123.1 (2)	C9—C10—H10	119.9
C3—C2—C1	122.3 (3)	C10—C11—C12	119.7 (3)
C3—C2—N2	116.1 (3)	C10—C11—H11	120.1
C1—C2—N2	121.6 (3)	C12—C11—H11	120.1
C2—C3—C4	118.9 (4)	C11—C12—C7	119.6 (3)
C2—C3—H3	120.5	C11—C12—H12	120.2
C4—C3—H3	120.5	C7—C12—H12	120.2
C3—C4—C5	120.2 (4)	C8—C13—H13A	109.5
C3—C4—H4	119.9	C8—C13—H13B	109.5
C5—C4—H4	119.9	H13A—C13—H13B	109.5
C4—C5—C6	120.7 (4)	C8—C13—H13C	109.5
C4—C5—H5	119.7	H13A—C13—H13C	109.5
C6—C5—H5	119.7	H13B—C13—H13C	109.5
C1—C6—C5	119.9 (4)	C7—N1—S1	122.66 (19)
C1—C6—H6	120.0	C7—N1—H1N	117 (2)
C5—C6—H6	120.0	S1—N1—H1N	114 (2)
C12—C7—C8	121.7 (3)	O4—N2—O3	125.3 (3)
C12—C7—N1	117.6 (3)	O4—N2—C2	117.1 (3)
C8—C7—N1	120.7 (3)	O3—N2—C2	117.6 (3)
C9—C8—C7	117.1 (3)	O2—S1—O1	119.68 (14)
C9—C8—C13	120.1 (3)	O2—S1—N1	107.28 (13)
C7—C8—C13	122.8 (3)	O1—S1—N1	107.24 (13)
C10—C9—C8	121.6 (3)	O2—S1—C1	107.74 (15)
C10—C9—H9	119.2	O1—S1—C1	106.47 (14)
C8—C9—H9	119.2	N1—S1—C1	107.96 (14)

C6—C1—C2—C3	−0.3 (5)	C10—C11—C12—C7	−1.5 (5)
S1—C1—C2—C3	179.1 (3)	C8—C7—C12—C11	1.4 (5)
C6—C1—C2—N2	177.8 (3)	N1—C7—C12—C11	179.2 (3)
S1—C1—C2—N2	−2.8 (4)	C12—C7—N1—S1	76.8 (3)
C1—C2—C3—C4	1.3 (7)	C8—C7—N1—S1	−105.4 (3)
N2—C2—C3—C4	−176.9 (4)	C3—C2—N2—O4	−56.9 (5)
C2—C3—C4—C5	−1.4 (8)	C1—C2—N2—O4	125.0 (4)
C3—C4—C5—C6	0.7 (9)	C3—C2—N2—O3	121.2 (4)
C2—C1—C6—C5	−0.5 (6)	C1—C2—N2—O3	−57.0 (4)
S1—C1—C6—C5	−179.9 (4)	C7—N1—S1—O2	−170.2 (2)
C4—C5—C6—C1	0.3 (8)	C7—N1—S1—O1	−40.5 (3)
C12—C7—C8—C9	0.3 (4)	C7—N1—S1—C1	73.9 (3)
N1—C7—C8—C9	−177.4 (3)	C6—C1—S1—O2	149.0 (3)
C12—C7—C8—C13	−179.5 (3)	C2—C1—S1—O2	−30.5 (3)
N1—C7—C8—C13	2.7 (4)	C6—C1—S1—O1	19.4 (3)
C7—C8—C9—C10	−2.0 (5)	C2—C1—S1—O1	−160.0 (3)
C13—C8—C9—C10	177.8 (3)	C6—C1—S1—N1	−95.5 (3)
C8—C9—C10—C11	1.9 (6)	C2—C1—S1—N1	85.1 (3)
C9—C10—C11—C12	−0.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.84 (2)	2.16 (2)	2.897 (3)	146 (3)
N1—H1N···O3	0.84 (2)	2.57 (3)	3.132 (4)	125 (3)

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂O₄S
M_r	292.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.2409 (7), 15.1531 (9), 10.5376 (8)
β (°)	107.775 (8)
V (Å³)	1405.13 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.28 × 0.14

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	0.930, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	5234, 2538, 2020
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.114, 1.21
No. of reflections	2538
No. of parameters	186
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)	0.33, −0.36

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	0.841 (17)	2.16 (2)	2.897 (3)	146 (3)
N1—H1N···O3	0.841 (17)	2.57 (3)	3.132 (4)	125 (3)

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

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

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