N-(2,5-Dimethyl­phen­yl)-2-nitro­benzene­sulfonamide

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

doi:10.1107/S1600536812047630

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3426

doi:10.1107/S1600536812047630

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N-(2,5-Dimethylphenyl)-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 16 November 2012; accepted 20 November 2012; online 24 November 2012)

In the crystal structure of the title compound, C₁₄H₁₄N₂O₄S, the N—H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and anti to the ortho- and syn to the meta-methyl groups in the aniline ring. The molecule is twisted at the S—N bond with a torsion angle of 71.41 (18)°. The dihedral angle between the planes of the benzene rings is 51.07 (8)°. In the crystal, pairs of N—H⋯O_sulfonamide hydrogen bonds link the molecules into inversion dimers.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-arylsulfonamides, see: Chaithanya et al. (2012 ); Gowda et al. (2002 ) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004 ); Shetty & Gowda (2004 ).

Experimental

Crystal data

C₁₄H₁₄N₂O₄S
M_r = 306.33
Triclinic, $[P \overline 1]$
a = 8.1987 (7) Å
b = 9.6729 (9) Å
c = 9.9328 (9) Å
α = 84.386 (9)°
β = 72.096 (8)°
γ = 89.239 (9)°
V = 745.86 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.36 × 0.24 × 0.16 mm

Data collection

Oxford Diffraction Xcaliburdiffractometer with 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 = 0.921, T_max = 0.964
4954 measured reflections
3027 independent reflections
2629 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.108
S = 1.14
3027 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.82 (2)	2.27 (2)	3.023 (2)	152 (2)
Symmetry code: (i) -x, -y, -z+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/S1600536812047630/rz5026sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812047630/rz5026Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812047630/rz5026Isup3.cml

checkCIF report

Comment top

As a part of studying the effect of substituents on the structures and other aspects of 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-(2,5-dimethylphenyl)-2-nitrobenzene- sulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and anti to the ortho-methyl and syn to the meta-methyl groups in the anilino ring, compared to the anti conformation observed between the N—H bond and both the ortho- and meta-methyl groups in the anilino ring observed in N-(2,3-dimethylphenyl)-2-nitrobenzene- sulfonamide (II) (Chaithanya et al., 2012).

The molecules in (I) are twisted at the S—N bond with the torsional angle of 71.41 (18)°, compared to the values of -60.37 (30) and 58.81 (34)° in the two independent molecules of (II).

The dihedral angle between the sulfonyl and the anilino rings is 51.07 (8)°, compared to the values of 53.67 (8) and 56.99 (9)° in the two molecules of (II).

The amide H-atom showed the intermolecular H-bonding with the sulfonyl oxygen atom of the other molecule, generating inversion dimers (Table 1, Fig. 2.)

In the crystal structure, N1—H1N···O2(S) intermolecular hydrogen bonds link the molecules into inversion dimers (Table 1, Fig. 2.)

Related literature top

For studies on the effects of substituents on the structures and other aspects of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2002) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004); Shetty & Gowda (2004).

Experimental top

The title compound was prepared by treating 2-nitrobenzenesulfonyl- chloride with 2,5-dimethylaniline 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-(2,5-dimethylphenyl)-2-nitrobenzenesulfon- amide 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. The purity of the compound was checked and characterized by its infrared spectra.

Prism like light brown 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-(2,5-Dimethylphenyl)-2-nitrobenzenesulfonamide top

Crystal data top

C₁₄H₁₄N₂O₄S	Z = 2
M_r = 306.33	F(000) = 320
Triclinic, P1	D_x = 1.364 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1987 (7) Å	Cell parameters from 3120 reflections
b = 9.6729 (9) Å	θ = 2.6–27.8°
c = 9.9328 (9) Å	µ = 0.23 mm⁻¹
α = 84.386 (9)°	T = 293 K
β = 72.096 (8)°	Prism, light brown
γ = 89.239 (9)°	0.36 × 0.24 × 0.16 mm
V = 745.86 (12) Å³

Data collection top

Oxford Diffraction Xcaliburdiffractometer with Sapphire CCD	3027 independent reflections
Radiation source: fine-focus sealed tube	2629 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→10
T_min = 0.921, T_max = 0.964	k = −12→11
4954 measured reflections	l = −12→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.0379P)² + 0.3685P] where P = (F_o² + 2F_c²)/3
3027 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.28 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₄S	γ = 89.239 (9)°
M_r = 306.33	V = 745.86 (12) Å³
Triclinic, P1	Z = 2
a = 8.1987 (7) Å	Mo Kα radiation
b = 9.6729 (9) Å	µ = 0.23 mm⁻¹
c = 9.9328 (9) Å	T = 293 K
α = 84.386 (9)°	0.36 × 0.24 × 0.16 mm
β = 72.096 (8)°

Data collection top

Oxford Diffraction Xcaliburdiffractometer with Sapphire CCD	3027 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2629 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.964	R_int = 0.011
4954 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.28 e Å⁻³
3027 reflections	Δρ_min = −0.29 e Å⁻³
193 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	0.3540 (2)	0.0929 (2)	0.6857 (2)	0.0387 (4)
C2	0.4684 (2)	0.0253 (2)	0.7467 (2)	0.0433 (4)
C3	0.6437 (3)	0.0467 (3)	0.6890 (3)	0.0561 (6)
H3	0.7187	−0.0016	0.7294	0.067*
C4	0.7051 (3)	0.1400 (3)	0.5713 (3)	0.0657 (7)
H4	0.8226	0.1564	0.5326	0.079*
C5	0.5947 (3)	0.2092 (3)	0.5104 (3)	0.0657 (7)
H5	0.6376	0.2732	0.4313	0.079*
C6	0.4199 (3)	0.1846 (2)	0.5655 (2)	0.0525 (5)
H6	0.3462	0.2299	0.5216	0.063*
C7	0.0552 (3)	0.3225 (2)	0.8314 (2)	0.0448 (5)
C8	0.1732 (3)	0.4106 (2)	0.8577 (2)	0.0567 (6)
C9	0.1583 (4)	0.5520 (3)	0.8214 (3)	0.0760 (8)
H9	0.2318	0.6147	0.8398	0.091*
C10	0.0386 (4)	0.6010 (3)	0.7595 (3)	0.0772 (9)
H10	0.0348	0.6961	0.7352	0.093*
C11	−0.0768 (4)	0.5141 (3)	0.7317 (3)	0.0701 (7)
C12	−0.0680 (3)	0.3728 (2)	0.7717 (2)	0.0546 (5)
H12	−0.1464	0.3114	0.7580	0.065*
C13	0.3075 (4)	0.3582 (3)	0.9231 (3)	0.0808 (9)
H13A	0.3794	0.2942	0.8642	0.121*
H13B	0.2531	0.3118	1.0159	0.121*
H13C	0.3759	0.4350	0.9310	0.121*
C14	−0.2091 (5)	0.5675 (4)	0.6626 (4)	0.1074 (12)
H14A	−0.1524	0.6151	0.5709	0.161*
H14B	−0.2833	0.6304	0.7213	0.161*
H14C	−0.2756	0.4907	0.6518	0.161*
N1	0.0568 (2)	0.17583 (17)	0.86856 (18)	0.0440 (4)
H1N	0.054 (3)	0.147 (2)	0.9500 (18)	0.053*
N2	0.4089 (3)	−0.0701 (2)	0.8773 (2)	0.0605 (5)
O1	0.06849 (18)	0.11008 (16)	0.63232 (16)	0.0524 (4)
O2	0.09053 (18)	−0.06778 (14)	0.82168 (17)	0.0530 (4)
O3	0.3174 (2)	−0.0226 (2)	0.98338 (19)	0.0766 (6)
O4	0.4595 (3)	−0.1884 (2)	0.8720 (3)	0.1039 (8)
S1	0.12780 (6)	0.06923 (5)	0.75061 (5)	0.04028 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0295 (9)	0.0461 (10)	0.0427 (10)	0.0008 (7)	−0.0130 (8)	−0.0090 (8)
C2	0.0392 (10)	0.0489 (11)	0.0462 (11)	0.0018 (8)	−0.0184 (8)	−0.0087 (9)
C3	0.0352 (10)	0.0803 (16)	0.0610 (14)	0.0081 (10)	−0.0235 (10)	−0.0184 (12)
C4	0.0340 (11)	0.107 (2)	0.0540 (13)	−0.0084 (12)	−0.0080 (10)	−0.0155 (13)
C5	0.0470 (12)	0.0948 (19)	0.0483 (13)	−0.0161 (12)	−0.0074 (10)	0.0054 (12)
C6	0.0427 (11)	0.0664 (14)	0.0482 (12)	−0.0028 (10)	−0.0159 (9)	0.0026 (10)
C7	0.0419 (10)	0.0408 (10)	0.0425 (10)	−0.0039 (8)	0.0003 (8)	−0.0034 (8)
C8	0.0508 (12)	0.0569 (13)	0.0516 (12)	−0.0120 (10)	0.0032 (10)	−0.0149 (10)
C9	0.0778 (18)	0.0586 (16)	0.0737 (18)	−0.0236 (14)	0.0073 (15)	−0.0178 (13)
C10	0.099 (2)	0.0401 (13)	0.0682 (17)	−0.0027 (14)	0.0094 (16)	−0.0016 (12)
C11	0.0859 (19)	0.0550 (15)	0.0579 (14)	0.0203 (13)	−0.0073 (13)	−0.0015 (11)
C12	0.0560 (13)	0.0474 (12)	0.0562 (13)	0.0057 (10)	−0.0110 (10)	−0.0070 (10)
C13	0.0585 (15)	0.101 (2)	0.090 (2)	−0.0091 (14)	−0.0240 (14)	−0.0389 (17)
C14	0.136 (3)	0.085 (2)	0.100 (3)	0.050 (2)	−0.041 (2)	0.0008 (19)
N1	0.0415 (9)	0.0426 (9)	0.0433 (9)	−0.0010 (7)	−0.0078 (7)	0.0007 (7)
N2	0.0507 (11)	0.0670 (13)	0.0716 (14)	−0.0038 (9)	−0.0350 (11)	0.0086 (10)
O1	0.0400 (7)	0.0664 (10)	0.0586 (9)	0.0051 (7)	−0.0254 (7)	−0.0112 (7)
O2	0.0451 (8)	0.0412 (8)	0.0708 (10)	−0.0064 (6)	−0.0158 (7)	−0.0025 (7)
O3	0.0671 (11)	0.1086 (16)	0.0516 (10)	−0.0154 (10)	−0.0196 (9)	0.0114 (10)
O4	0.1010 (17)	0.0670 (13)	0.147 (2)	0.0127 (12)	−0.0545 (16)	0.0241 (13)
S1	0.0304 (2)	0.0421 (3)	0.0500 (3)	−0.00165 (17)	−0.01472 (19)	−0.0047 (2)

Geometric parameters (Å, º) top

C1—C6	1.383 (3)	C9—H9	0.9300
C1—C2	1.389 (3)	C10—C11	1.380 (4)
C1—S1	1.7764 (18)	C10—H10	0.9300
C2—C3	1.384 (3)	C11—C12	1.392 (3)
C2—N2	1.470 (3)	C11—C14	1.512 (4)
C3—C4	1.371 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.369 (4)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.383 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—C12	1.382 (3)	N1—S1	1.6049 (18)
C7—C8	1.397 (3)	N1—H1N	0.823 (16)
C7—N1	1.431 (3)	N2—O4	1.213 (3)
C8—C9	1.393 (4)	N2—O3	1.218 (3)
C8—C13	1.500 (4)	O1—S1	1.4242 (15)
C9—C10	1.367 (5)	O2—S1	1.4295 (15)

C6—C1—C2	118.12 (18)	C10—C11—C12	116.9 (3)
C6—C1—S1	117.31 (15)	C10—C11—C14	122.5 (3)
C2—C1—S1	124.57 (15)	C12—C11—C14	120.6 (3)
C3—C2—C1	121.6 (2)	C7—C12—C11	121.1 (2)
C3—C2—N2	116.78 (18)	C7—C12—H12	119.4
C1—C2—N2	121.63 (18)	C11—C12—H12	119.4
C4—C3—C2	119.0 (2)	C8—C13—H13A	109.5
C4—C3—H3	120.5	C8—C13—H13B	109.5
C2—C3—H3	120.5	H13A—C13—H13B	109.5
C5—C4—C3	120.4 (2)	C8—C13—H13C	109.5
C5—C4—H4	119.8	H13A—C13—H13C	109.5
C3—C4—H4	119.8	H13B—C13—H13C	109.5
C4—C5—C6	120.5 (2)	C11—C14—H14A	109.5
C4—C5—H5	119.7	C11—C14—H14B	109.5
C6—C5—H5	119.7	H14A—C14—H14B	109.5
C5—C6—C1	120.3 (2)	C11—C14—H14C	109.5
C5—C6—H6	119.9	H14A—C14—H14C	109.5
C1—C6—H6	119.9	H14B—C14—H14C	109.5
C12—C7—C8	121.8 (2)	C7—N1—S1	121.88 (14)
C12—C7—N1	117.78 (19)	C7—N1—H1N	119.0 (17)
C8—C7—N1	120.4 (2)	S1—N1—H1N	115.8 (17)
C9—C8—C7	116.1 (2)	O4—N2—O3	125.3 (2)
C9—C8—C13	121.2 (2)	O4—N2—C2	117.4 (2)
C7—C8—C13	122.6 (2)	O3—N2—C2	117.3 (2)
C10—C9—C8	121.9 (3)	O1—S1—O2	119.85 (9)
C10—C9—H9	119.1	O1—S1—N1	108.74 (9)
C8—C9—H9	119.1	O2—S1—N1	107.05 (9)
C9—C10—C11	122.1 (2)	O1—S1—C1	105.37 (9)
C9—C10—H10	118.9	O2—S1—C1	108.28 (9)
C11—C10—H10	118.9	N1—S1—C1	106.93 (9)

C6—C1—C2—C3	−0.9 (3)	C8—C7—C12—C11	1.7 (3)
S1—C1—C2—C3	178.74 (16)	N1—C7—C12—C11	−179.5 (2)
C6—C1—C2—N2	177.9 (2)	C10—C11—C12—C7	−2.4 (4)
S1—C1—C2—N2	−2.5 (3)	C14—C11—C12—C7	178.3 (2)
C1—C2—C3—C4	2.1 (3)	C12—C7—N1—S1	75.0 (2)
N2—C2—C3—C4	−176.8 (2)	C8—C7—N1—S1	−106.1 (2)
C2—C3—C4—C5	−1.2 (4)	C3—C2—N2—O4	−59.0 (3)
C3—C4—C5—C6	−0.8 (4)	C1—C2—N2—O4	122.2 (2)
C4—C5—C6—C1	2.0 (4)	C3—C2—N2—O3	118.6 (2)
C2—C1—C6—C5	−1.2 (3)	C1—C2—N2—O3	−60.2 (3)
S1—C1—C6—C5	179.19 (19)	C7—N1—S1—O1	−41.91 (18)
C12—C7—C8—C9	0.5 (3)	C7—N1—S1—O2	−172.73 (15)
N1—C7—C8—C9	−178.28 (19)	C7—N1—S1—C1	71.41 (18)
C12—C7—C8—C13	179.7 (2)	C6—C1—S1—O1	22.19 (19)
N1—C7—C8—C13	0.9 (3)	C2—C1—S1—O1	−157.44 (17)
C7—C8—C9—C10	−2.0 (4)	C6—C1—S1—O2	151.56 (17)
C13—C8—C9—C10	178.8 (2)	C2—C1—S1—O2	−28.1 (2)
C8—C9—C10—C11	1.3 (4)	C6—C1—S1—N1	−93.39 (18)
C9—C10—C11—C12	0.9 (4)	C2—C1—S1—N1	86.97 (18)
C9—C10—C11—C14	−179.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.82 (2)	2.27 (2)	3.023 (2)	152 (2)

Symmetry code: (i) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O₄S
M_r	306.33
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.1987 (7), 9.6729 (9), 9.9328 (9)
α, β, γ (°)	84.386 (9), 72.096 (8), 89.239 (9)
V (Å³)	745.86 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.36 × 0.24 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcaliburdiffractometer with Sapphire CCD
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.921, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	4954, 3027, 2629
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.108, 1.14
No. of reflections	3027
No. of parameters	193
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)	0.28, −0.29

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	0.823 (16)	2.273 (18)	3.023 (2)	152 (2)

Symmetry code: (i) −x, −y, −z+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.

References

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