N-(2-Chloro­benzo­yl)-3-nitro­benzene­sulfonamide

Suchetan, P.A.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536812003236

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o543

doi:10.1107/S1600536812003236

Open

access

N-(2-Chlorobenzoyl)-3-nitrobenzenesulfonamide

P. A. Suchetan,^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 24 January 2012; accepted 25 January 2012; online 31 January 2012)

In the molecule of the title compound, C₁₃H₉ClN₂O₅S, the dihedral angle between the two aromatic rings is 84.3 (1)°. In the crystal, molecules are linked into chains via N—H⋯O(S) hydrogen bonds.

Related literature

For studies, including ours, of the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003 ); Gowda et al. (1999 , 2003 ); of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ); of N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005 ); of N-(substituted benzoyl)-arylsulfonamides, see: Suchetan et al. (2012 ); of N-chloroarylamides, see: Jyothi & Gowda (2004 ); and of N-bromoarylsulfonamides, see: Usha & Gowda (2006 ).

Experimental

Crystal data

C₁₃H₉ClN₂O₅S
M_r = 340.73
Monoclinic, P 2₁ /n
a = 14.606 (2) Å
b = 5.1159 (4) Å
c = 18.742 (2) Å
β = 93.336 (9)°
V = 1398.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 293 K
0.36 × 0.10 × 0.06 mm

Data collection

Oxford Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.855, T_max = 0.974
5313 measured reflections
2844 independent reflections
2005 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.104
S = 1.19
2844 reflections
202 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 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	0.83 (2)	2.09 (2)	2.919 (3)	173 (3)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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/S1600536812003236/bt5798sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003236/bt5798Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812003236/bt5798Isup3.cml

checkCIF report

Comment top

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 1999, 2003), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005); N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al., 2012); N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(2-chlorobenzoyl)-3-nitrobenzenesulfonamide (I) has been determined (Fig.1).

The conformation between the N—H and C═O bonds in the C—SO₂—NH—C(O) segment is anti and the N—C bond in the segment has gauche torsion with respect to the S═O bonds (Fig. 1), similar to that observed in N-(3-chlorobenzoyl)-3-nitrobenzene-sulfonamide (II) (Suchetan et al., 2012). Further, in (I), the conformation between the N—H bond and the meta-nitro group in the sulfonyl benzene ring is syn, similar to that observed in (II). The conformation of the C═O is also syn to the ortho-Cl atom in the benzoyl ring, in contrast to the anti conformation observed between the C═O and the meta-Cl atom in (II)

The molecule is twisted at the S—N bond with the torsional angle of -61.82 (29)°, compared to the value of -60.40 (29)° in (II).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 80.4 (1)°, compared to the value of 77.0 (1)° in (II). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 84.3 (1)°, compared to the value of 83.5 (1)° in (II).

The packing of molecules linked by of N—H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature top

For studies, including ours, of the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (1999, 2003); of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007); of N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005); of N-(substituted benzoyl)-arylsulfonamides, see: Suchetan et al. (2012); of N-chloroarylamides, see: Jyothi & Gowda (2004); and of N-bromoarylsulfonamides, see: Usha & Gowda (2006).

Experimental top

The title compound was prepared by refluxing a mixture of 2-chlorobenzoic acid (0.02 mole), 3-nitrobenzenesulfonamide (0.02 mole) and excess phosphorous oxychloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, N-(2-chlorobenzoyl)-3-nitrobenzenesulfonamide, obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.

Rod like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of its toluene solution 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 the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

N-(2-Chlorobenzoyl)-3-nitrobenzenesulfonamide top

Crystal data top

C₁₃H₉ClN₂O₅S	F(000) = 696
M_r = 340.73	D_x = 1.619 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1612 reflections
a = 14.606 (2) Å	θ = 2.6–27.7°
b = 5.1159 (4) Å	µ = 0.45 mm⁻¹
c = 18.742 (2) Å	T = 293 K
β = 93.336 (9)°	Rod, colourless
V = 1398.1 (3) Å³	0.36 × 0.10 × 0.06 mm
Z = 4

Data collection top

Oxford Xcalibur diffractometer with Sapphire CCD detector	2844 independent reflections
Radiation source: fine-focus sealed tube	2005 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 3.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −17→18
T_min = 0.855, T_max = 0.974	k = −6→6
5313 measured reflections	l = −23→14

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ²(F_o²) + (0.0156P)² + 1.9016P] where P = (F_o² + 2F_c²)/3
2844 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.27 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₉ClN₂O₅S	V = 1398.1 (3) Å³
M_r = 340.73	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.606 (2) Å	µ = 0.45 mm⁻¹
b = 5.1159 (4) Å	T = 293 K
c = 18.742 (2) Å	0.36 × 0.10 × 0.06 mm
β = 93.336 (9)°

Data collection top

Oxford Xcalibur diffractometer with Sapphire CCD detector	2844 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2005 reflections with I > 2σ(I)
T_min = 0.855, T_max = 0.974	R_int = 0.028
5313 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	1 restraint
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	Δρ_max = 0.27 e Å⁻³
2844 reflections	Δρ_min = −0.29 e Å⁻³
202 parameters

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
C1	0.1617 (2)	0.3605 (6)	0.91163 (16)	0.0303 (7)
C2	0.2244 (2)	0.5563 (6)	0.92952 (17)	0.0327 (8)
H2	0.2658	0.6146	0.8971	0.039*
C3	0.2233 (2)	0.6616 (7)	0.99714 (17)	0.0340 (8)
C4	0.1637 (2)	0.5785 (7)	1.04683 (18)	0.0405 (9)
H4	0.1647	0.6535	1.0921	0.049*
C5	0.1028 (3)	0.3823 (8)	1.02791 (18)	0.0454 (10)
H5	0.0627	0.3218	1.0610	0.055*
C6	0.1003 (2)	0.2736 (7)	0.96009 (18)	0.0395 (9)
H6	0.0580	0.1437	0.9472	0.047*
C7	0.0183 (2)	0.4942 (6)	0.77389 (16)	0.0301 (7)
C8	−0.0148 (2)	0.6786 (6)	0.71599 (16)	0.0292 (7)
C9	−0.0867 (2)	0.8548 (7)	0.72383 (17)	0.0343 (8)
C10	−0.1108 (3)	1.0338 (7)	0.67100 (19)	0.0443 (9)
H10	−0.1579	1.1521	0.6774	0.053*
C11	−0.0651 (3)	1.0377 (8)	0.60867 (19)	0.0498 (10)
H11	−0.0807	1.1605	0.5735	0.060*
C12	0.0037 (3)	0.8594 (8)	0.59861 (18)	0.0491 (10)
H12	0.0333	0.8586	0.5560	0.059*
C13	0.0285 (2)	0.6831 (7)	0.65139 (16)	0.0381 (8)
H13	0.0751	0.5639	0.6440	0.046*
N1	0.10998 (18)	0.4193 (5)	0.76979 (13)	0.0299 (6)
H1N	0.1464 (19)	0.515 (6)	0.7492 (16)	0.036*
N2	0.2880 (2)	0.8740 (6)	1.01653 (16)	0.0460 (8)
O1	0.11150 (18)	−0.0212 (4)	0.82834 (12)	0.0460 (7)
O2	0.25475 (16)	0.2152 (5)	0.80566 (12)	0.0443 (6)
O3	−0.02699 (16)	0.4097 (5)	0.82055 (12)	0.0427 (6)
O4	0.2823 (2)	0.9787 (6)	1.07436 (15)	0.0686 (9)
O5	0.3436 (2)	0.9354 (6)	0.97376 (15)	0.0724 (10)
Cl1	−0.14856 (7)	0.8669 (2)	0.80000 (5)	0.0528 (3)
S1	0.16187 (6)	0.21592 (16)	0.82617 (4)	0.0321 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0364 (18)	0.0269 (18)	0.0272 (16)	0.0043 (16)	−0.0002 (14)	0.0024 (14)
C2	0.0375 (19)	0.0297 (19)	0.0310 (17)	0.0041 (16)	0.0042 (14)	0.0028 (15)
C3	0.0378 (19)	0.0322 (19)	0.0314 (17)	0.0017 (17)	−0.0026 (14)	−0.0030 (15)
C4	0.045 (2)	0.046 (2)	0.0303 (18)	0.0063 (19)	0.0006 (16)	−0.0068 (17)
C5	0.046 (2)	0.058 (3)	0.0327 (18)	−0.002 (2)	0.0094 (16)	0.0058 (19)
C6	0.039 (2)	0.042 (2)	0.0374 (19)	−0.0046 (18)	0.0026 (15)	0.0026 (17)
C7	0.0307 (18)	0.0299 (18)	0.0295 (17)	−0.0044 (15)	0.0009 (14)	−0.0040 (15)
C8	0.0277 (17)	0.0306 (18)	0.0289 (16)	−0.0040 (15)	−0.0030 (13)	−0.0012 (14)
C9	0.0305 (18)	0.041 (2)	0.0316 (17)	−0.0018 (17)	0.0004 (14)	−0.0038 (16)
C10	0.042 (2)	0.043 (2)	0.047 (2)	0.0105 (19)	−0.0038 (17)	0.0013 (19)
C11	0.060 (3)	0.051 (3)	0.037 (2)	0.012 (2)	−0.0019 (19)	0.0154 (19)
C12	0.054 (2)	0.063 (3)	0.0307 (19)	0.008 (2)	0.0058 (17)	0.0055 (19)
C13	0.0383 (19)	0.049 (2)	0.0272 (17)	0.0081 (18)	0.0031 (14)	0.0026 (17)
N1	0.0308 (16)	0.0316 (16)	0.0275 (14)	−0.0010 (13)	0.0019 (11)	0.0052 (12)
N2	0.052 (2)	0.0432 (19)	0.0419 (18)	−0.0030 (17)	−0.0049 (16)	−0.0041 (16)
O1	0.0690 (18)	0.0245 (13)	0.0436 (14)	−0.0033 (13)	−0.0048 (13)	0.0003 (11)
O2	0.0416 (14)	0.0530 (16)	0.0385 (13)	0.0174 (13)	0.0040 (11)	−0.0081 (12)
O3	0.0404 (14)	0.0489 (16)	0.0397 (13)	0.0002 (13)	0.0118 (11)	0.0108 (12)
O4	0.076 (2)	0.070 (2)	0.0592 (18)	−0.0126 (17)	0.0022 (16)	−0.0354 (16)
O5	0.084 (2)	0.079 (2)	0.0552 (18)	−0.0441 (19)	0.0119 (17)	−0.0091 (17)
Cl1	0.0486 (6)	0.0624 (7)	0.0493 (5)	0.0118 (5)	0.0195 (4)	0.0037 (5)
S1	0.0401 (5)	0.0272 (4)	0.0288 (4)	0.0064 (4)	0.0003 (3)	−0.0023 (4)

Geometric parameters (Å, º) top

C1—C6	1.386 (4)	C8—C9	1.398 (5)
C1—C2	1.386 (4)	C9—C10	1.379 (5)
C1—S1	1.764 (3)	C9—Cl1	1.735 (3)
C2—C3	1.378 (4)	C10—C11	1.379 (5)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.379 (5)	C11—C12	1.377 (5)
C3—N2	1.471 (4)	C11—H11	0.9300
C4—C5	1.374 (5)	C12—C13	1.372 (5)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.386 (5)	C13—H13	0.9300
C5—H5	0.9300	N1—S1	1.637 (3)
C6—H6	0.9300	N1—H1N	0.834 (18)
C7—O3	1.207 (4)	N2—O5	1.216 (4)
C7—N1	1.399 (4)	N2—O4	1.216 (4)
C7—C8	1.497 (4)	O1—S1	1.421 (2)
C8—C13	1.398 (4)	O2—S1	1.431 (2)

C6—C1—C2	121.1 (3)	C8—C9—Cl1	122.7 (3)
C6—C1—S1	119.7 (3)	C11—C10—C9	120.1 (3)
C2—C1—S1	119.1 (2)	C11—C10—H10	119.9
C3—C2—C1	117.5 (3)	C9—C10—H10	119.9
C3—C2—H2	121.2	C12—C11—C10	119.9 (3)
C1—C2—H2	121.2	C12—C11—H11	120.0
C2—C3—C4	122.9 (3)	C10—C11—H11	120.0
C2—C3—N2	118.3 (3)	C13—C12—C11	120.1 (3)
C4—C3—N2	118.8 (3)	C13—C12—H12	120.0
C5—C4—C3	118.4 (3)	C11—C12—H12	120.0
C5—C4—H4	120.8	C12—C13—C8	121.4 (3)
C3—C4—H4	120.8	C12—C13—H13	119.3
C4—C5—C6	120.8 (3)	C8—C13—H13	119.3
C4—C5—H5	119.6	C7—N1—S1	123.2 (2)
C6—C5—H5	119.6	C7—N1—H1N	120 (2)
C1—C6—C5	119.3 (3)	S1—N1—H1N	113 (2)
C1—C6—H6	120.3	O5—N2—O4	123.8 (3)
C5—C6—H6	120.3	O5—N2—C3	118.2 (3)
O3—C7—N1	120.6 (3)	O4—N2—C3	118.0 (3)
O3—C7—C8	125.7 (3)	O1—S1—O2	120.39 (16)
N1—C7—C8	113.8 (3)	O1—S1—N1	109.88 (15)
C13—C8—C9	117.4 (3)	O2—S1—N1	103.81 (14)
C13—C8—C7	119.7 (3)	O1—S1—C1	107.69 (15)
C9—C8—C7	122.9 (3)	O2—S1—C1	107.25 (15)
C10—C9—C8	121.0 (3)	N1—S1—C1	107.12 (15)
C10—C9—Cl1	116.3 (3)

C6—C1—C2—C3	−0.2 (5)	C9—C10—C11—C12	1.2 (6)
S1—C1—C2—C3	−178.9 (2)	C10—C11—C12—C13	−1.9 (6)
C1—C2—C3—C4	0.6 (5)	C11—C12—C13—C8	0.2 (6)
C1—C2—C3—N2	−178.6 (3)	C9—C8—C13—C12	2.2 (5)
C2—C3—C4—C5	0.0 (5)	C7—C8—C13—C12	−176.2 (3)
N2—C3—C4—C5	179.2 (3)	O3—C7—N1—S1	0.2 (4)
C3—C4—C5—C6	−1.0 (6)	C8—C7—N1—S1	−179.1 (2)
C2—C1—C6—C5	−0.9 (5)	C2—C3—N2—O5	−4.8 (5)
S1—C1—C6—C5	177.9 (3)	C4—C3—N2—O5	175.9 (3)
C4—C5—C6—C1	1.5 (5)	C2—C3—N2—O4	174.9 (3)
O3—C7—C8—C13	−154.9 (3)	C4—C3—N2—O4	−4.4 (5)
N1—C7—C8—C13	24.4 (4)	C7—N1—S1—O1	54.9 (3)
O3—C7—C8—C9	26.8 (5)	C7—N1—S1—O2	−175.1 (3)
N1—C7—C8—C9	−153.9 (3)	C7—N1—S1—C1	−61.8 (3)
C13—C8—C9—C10	−2.9 (5)	C6—C1—S1—O1	−15.0 (3)
C7—C8—C9—C10	175.4 (3)	C2—C1—S1—O1	163.7 (2)
C13—C8—C9—Cl1	178.4 (3)	C6—C1—S1—O2	−146.0 (3)
C7—C8—C9—Cl1	−3.2 (5)	C2—C1—S1—O2	32.8 (3)
C8—C9—C10—C11	1.3 (6)	C6—C1—S1—N1	103.1 (3)
Cl1—C9—C10—C11	−180.0 (3)	C2—C1—S1—N1	−78.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.83 (2)	2.09 (2)	2.919 (3)	173 (3)

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉ClN₂O₅S
M_r	340.73
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	14.606 (2), 5.1159 (4), 18.742 (2)
β (°)	93.336 (9)
V (Å³)	1398.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.45
Crystal size (mm)	0.36 × 0.10 × 0.06

Data collection
Diffractometer	Oxford Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.855, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	5313, 2844, 2005
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.104, 1.19
No. of reflections	2844
No. of parameters	202
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)	0.27, −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	0.834 (18)	2.088 (19)	2.919 (3)	173 (3)

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

Acknowledgements

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

References

Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1–o3. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Gowda, B. T., Bhat, D. K., Fuess, H. & Weiss, A. (1999). Z. Naturforsch. Teil A, 54, 261–267. CAS Google Scholar
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2337. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Usha, K. M. & Jayalakshmi, K. L. (2003). Z. Naturforsch. Teil A, 61, 801–806. Google Scholar
Jyothi, K. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 64–68. CAS Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. 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. (2005). Z. Naturforsch. Teil A, 60, 113–120. CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suchetan, P. A., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o244. Web of Science CSD CrossRef IUCr Journals Google Scholar
Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351–359. Web of Science CrossRef CAS Google Scholar