Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 2| February 2012| Page o274
doi:10.1107/S1600536811054882

N-(2-Chloro­benzo­yl)-2-nitro­benzene­sulfonamide

P. A. Suchetan,a Sabine Forob and B. Thimme Gowdaa*

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 20 December 2011; accepted 20 December 2011; online 7 January 2012)

In the title compound, C13H9ClN2O5S, the dihedral angle between the two rings is 71.2 (1)°. The crystal structure features inversion dimers linked by pairs of N—H⋯O(S) hydrogen bonds.

Related literature

For studies, including our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bowes et al. (2003[Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.]); Gowda et al. (2006[Gowda, B. T., Kozisek, J. & Fuess, H. (2006). Z. Naturforsch. Teil A, 61, 588-594.]), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2339.]), on N-(ar­yl)-aryl­sulfonamides, see: Shetty & Gowda (2005[Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113-120.]), on N-(substitutedbenzo­yl)-aryl­sulfon­amides, see: Suchetan et al. (2012[Suchetan, P. A., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o244.]) and on N-chloro­aryl­amides, see: Gowda & Mahadevappa (1983[Gowda, B. T. & Mahadevappa, D. S. (1983). Talanta, 30, 359-362.]).

[Scheme 1]

Experimental

Crystal data

  • C13H9ClN2O5S

  • Mr = 340.73

  • Orthorhombic, P b c a

  • a = 12.266 (1) Å

  • b = 12.643 (1) Å

  • c = 18.738 (2) Å

  • V = 2905.9 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.43 mm−1

  • T = 293 K

  • 0.48 × 0.40 × 0.20 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.]) Tmin = 0.820, Tmax = 0.919

  • 7231 measured reflections

  • 2958 independent reflections

  • 2105 reflections with I > 2σ(I)

  • Rint = 0.015
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.096

  • S = 1.04

  • 2958 reflections

  • 202 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.23 e Å−3

  • Δρmin = −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 (1) 2.13 (1) 2.9465 (19) 172 (2)
Symmetry code: (i) -x, -y+1, -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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054882/bt5759sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054882/bt5759Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811054882/bt5759Isup3.cml

checkCIF report


Comment top

Diaryl acylsulfonamides are known as potent antitumor agents. 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., 2006), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005); N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al., 2012) and N-chloro-arylsulfonamides (Gowda & Mahadevappa, 1983), in the present work, the crystal structure of N-(2-chlorobenzoyl)-2-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-nitrobenzenesulfonamide (II)(Suchetan et al., 2012). In (I), the conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring is syn, similar to that observed between the N—H bond and the meta-nitro group in (II). Further, the conformation of the C═O is anti to the ortho-Cl atom in the benzoyl ring, similar to that 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 -59.68 (17)°, 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 77.5 (1)°, compared to the value of 77.0 (1)° in (II). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 71.2 (1)°, compared to the value of 83.5 (1)° in (II).

In the crystal, the intermolecular N–H···O (S) hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers. Part of the crystal structure is shown in Fig. 2.

Related literature top

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2006), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2012) and on N-chloroarylamides, see: Gowda & Mahadevappa (1983).

Experimental top

The title compound was prepared by refluxing a mixture of 2-chlorobenzoic acid (0.02 mole), 2-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)-2-nitrobenzenesulfonamide, obtained was filtered, washed thoroughly with water and then dissolved in a sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.

Prism 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.

Refinement top

The H atom of the NH group was located in a difference map and its coordinates were refined with a distance restraint of 0.86 (2) %A. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93 Å. All H atoms were refined with isotropic displacement parameters set to 1.2 times of the Ueq of the parent atom.

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
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.
N-(2-Chlorobenzoyl)-2-nitrobenzenesulfonamide top
Crystal data top
C13H9ClN2O5SF(000) = 1392
Mr = 340.73Dx = 1.558 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2278 reflections
a = 12.266 (1) Åθ = 2.5–27.7°
b = 12.643 (1) ŵ = 0.43 mm−1
c = 18.738 (2) ÅT = 293 K
V = 2905.9 (5) Å3Prism, colourless
Z = 80.48 × 0.40 × 0.20 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2958 independent reflections
Radiation source: fine-focus sealed tube2105 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −13→15
Tmin = 0.820, Tmax = 0.919k = −12→15
7231 measured reflectionsl = −23→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.052P)2 + 0.3259P]
where P = (Fo2 + 2Fc2)/3
2958 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.23 e Å−3
1 restraintΔρmin = −0.29 e Å−3
Crystal data top
C13H9ClN2O5SV = 2905.9 (5) Å3
Mr = 340.73Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.266 (1) ŵ = 0.43 mm−1
b = 12.643 (1) ÅT = 293 K
c = 18.738 (2) Å0.48 × 0.40 × 0.20 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2958 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		2105 reflections with I > 2σ(I)
Tmin = 0.820, Tmax = 0.919Rint = 0.015
7231 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0371 restraint
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.23 e Å−3
2958 reflectionsΔρmin = −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
xyzUiso*/Ueq
C10.08013 (14)0.23007 (14)0.52361 (9)0.0378 (4)
C20.00268 (15)0.21928 (14)0.57758 (10)0.0414 (4)
C3−0.01230 (19)0.12473 (16)0.61266 (12)0.0579 (6)
H3−0.06410.11940.64870.069*
C40.0493 (2)0.03845 (17)0.59424 (14)0.0698 (7)
H40.0393−0.02560.61780.084*
C50.12540 (19)0.04664 (18)0.54136 (14)0.0679 (7)
H50.1667−0.01220.52880.081*
C60.14160 (17)0.14199 (16)0.50620 (12)0.0523 (5)
H60.19420.14670.47060.063*
C7−0.00470 (16)0.32241 (14)0.36776 (9)0.0409 (4)
C8−0.08836 (15)0.37301 (15)0.32102 (9)0.0396 (4)
C9−0.18466 (17)0.32223 (16)0.30359 (11)0.0504 (5)
C10−0.2584 (2)0.3683 (2)0.25752 (13)0.0705 (7)
H10−0.32280.33340.24590.085*
C11−0.2364 (2)0.4656 (2)0.22895 (13)0.0741 (7)
H11−0.28590.49620.19760.089*
C12−0.1425 (2)0.51844 (19)0.24594 (11)0.0638 (7)
H12−0.12830.58460.22630.077*
C13−0.06890 (18)0.47285 (16)0.29256 (10)0.0496 (5)
H13−0.00580.50920.30500.060*
N10.02375 (13)0.38393 (11)0.42595 (8)0.0391 (4)
H1N−0.0179 (15)0.4312 (12)0.4385 (10)0.047*
N2−0.06860 (14)0.30632 (13)0.60028 (10)0.0515 (4)
O10.21732 (10)0.33502 (11)0.44685 (8)0.0546 (4)
O20.11350 (10)0.43253 (10)0.53775 (7)0.0425 (3)
O30.03763 (13)0.23796 (11)0.35641 (8)0.0616 (4)
O4−0.10433 (11)0.36567 (12)0.55488 (9)0.0617 (4)
O5−0.08870 (17)0.31359 (14)0.66363 (9)0.0915 (6)
Cl1−0.21604 (5)0.20111 (5)0.34182 (4)0.0802 (2)
S10.11830 (4)0.35192 (4)0.48410 (2)0.03738 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0299 (9)0.0363 (9)0.0473 (11)0.0011 (8)−0.0029 (8)0.0011 (8)
C20.0403 (10)0.0352 (9)0.0487 (11)0.0010 (8)0.0007 (9)0.0025 (8)
C30.0635 (14)0.0468 (12)0.0634 (13)−0.0006 (11)0.0106 (11)0.0138 (10)
C40.0751 (17)0.0445 (12)0.0897 (19)0.0078 (12)0.0053 (15)0.0198 (12)
C50.0591 (14)0.0412 (12)0.103 (2)0.0199 (11)0.0002 (14)0.0047 (12)
C60.0400 (11)0.0453 (11)0.0716 (14)0.0073 (9)0.0082 (10)−0.0014 (10)
C70.0458 (11)0.0393 (10)0.0377 (10)−0.0012 (9)0.0036 (9)−0.0050 (8)
C80.0442 (10)0.0427 (10)0.0319 (9)0.0040 (9)0.0023 (8)−0.0100 (8)
C90.0492 (12)0.0554 (12)0.0467 (11)−0.0016 (10)0.0015 (10)−0.0117 (10)
C100.0534 (14)0.0891 (18)0.0689 (14)0.0072 (14)−0.0158 (12)−0.0157 (15)
C110.0748 (18)0.0890 (19)0.0585 (14)0.0365 (16)−0.0122 (14)−0.0051 (13)
C120.0891 (19)0.0533 (13)0.0490 (12)0.0234 (13)0.0107 (13)0.0015 (11)
C130.0622 (13)0.0445 (11)0.0420 (10)0.0046 (10)0.0013 (10)−0.0058 (9)
N10.0427 (9)0.0377 (8)0.0369 (8)0.0057 (7)−0.0033 (7)−0.0040 (7)
N20.0510 (10)0.0386 (9)0.0648 (12)−0.0051 (9)0.0179 (9)−0.0005 (8)
O10.0371 (8)0.0643 (9)0.0626 (9)−0.0019 (7)0.0130 (7)0.0056 (7)
O20.0455 (7)0.0375 (7)0.0444 (7)−0.0043 (6)−0.0091 (6)−0.0018 (5)
O30.0694 (10)0.0515 (9)0.0638 (10)0.0196 (8)−0.0084 (8)−0.0189 (7)
O40.0478 (9)0.0516 (9)0.0857 (11)0.0121 (7)0.0126 (8)0.0112 (9)
O50.1402 (18)0.0662 (11)0.0681 (12)0.0066 (11)0.0497 (12)−0.0041 (9)
Cl10.0745 (5)0.0688 (4)0.0972 (5)−0.0255 (3)0.0024 (4)−0.0002 (3)
S10.0315 (2)0.0384 (3)0.0423 (3)−0.0029 (2)0.0002 (2)0.0017 (2)
Geometric parameters (Å, º) top
C1—C61.384 (3)C8—C131.391 (3)
C1—C21.394 (2)C9—C101.379 (3)
C1—S11.7721 (18)C9—Cl11.734 (2)
C2—C31.376 (3)C10—C111.369 (3)
C2—N21.468 (2)C10—H100.9300
C3—C41.371 (3)C11—C121.369 (3)
C3—H30.9300C11—H110.9300
C4—C51.365 (3)C12—C131.382 (3)
C4—H40.9300C12—H120.9300
C5—C61.388 (3)C13—H130.9300
C5—H50.9300N1—S11.6420 (16)
C6—H60.9300N1—H1N0.820 (14)
C7—O31.206 (2)N2—O51.216 (2)
C7—N11.384 (2)N2—O41.216 (2)
C7—C81.493 (3)O1—S11.4171 (13)
C8—C91.384 (3)O2—S11.4327 (13)
C6—C1—C2117.61 (17)C8—C9—Cl1120.13 (16)
C6—C1—S1117.21 (15)C11—C10—C9119.6 (2)
C2—C1—S1124.62 (14)C11—C10—H10120.2
C3—C2—C1121.49 (18)C9—C10—H10120.2
C3—C2—N2115.66 (17)C10—C11—C12120.9 (2)
C1—C2—N2122.85 (16)C10—C11—H11119.5
C4—C3—C2119.8 (2)C12—C11—H11119.5
C4—C3—H3120.1C11—C12—C13119.5 (2)
C2—C3—H3120.1C11—C12—H12120.2
C5—C4—C3120.0 (2)C13—C12—H12120.2
C5—C4—H4120.0C12—C13—C8120.6 (2)
C3—C4—H4120.0C12—C13—H13119.7
C4—C5—C6120.5 (2)C8—C13—H13119.7
C4—C5—H5119.7C7—N1—S1124.22 (13)
C6—C5—H5119.7C7—N1—H1N118.5 (14)
C1—C6—C5120.6 (2)S1—N1—H1N115.4 (14)
C1—C6—H6119.7O5—N2—O4124.28 (19)
C5—C6—H6119.7O5—N2—C2117.40 (18)
O3—C7—N1121.86 (18)O4—N2—C2118.31 (17)
O3—C7—C8124.88 (17)O1—S1—O2119.21 (8)
N1—C7—C8113.24 (15)O1—S1—N1108.40 (8)
C9—C8—C13118.50 (19)O2—S1—N1105.14 (7)
C9—C8—C7121.76 (18)O1—S1—C1107.53 (8)
C13—C8—C7119.73 (17)O2—S1—C1108.33 (8)
C10—C9—C8120.8 (2)N1—S1—C1107.76 (8)
C10—C9—Cl1119.05 (18)
C6—C1—C2—C30.2 (3)C9—C10—C11—C12−0.6 (4)
S1—C1—C2—C3−170.90 (16)C10—C11—C12—C130.1 (3)
C6—C1—C2—N2−179.14 (18)C11—C12—C13—C81.4 (3)
S1—C1—C2—N29.8 (3)C9—C8—C13—C12−2.3 (3)
C1—C2—C3—C4−0.5 (3)C7—C8—C13—C12176.28 (17)
N2—C2—C3—C4178.9 (2)O3—C7—N1—S11.6 (3)
C2—C3—C4—C50.1 (4)C8—C7—N1—S1−176.52 (12)
C3—C4—C5—C60.4 (4)C3—C2—N2—O538.4 (3)
C2—C1—C6—C50.4 (3)C1—C2—N2—O5−142.2 (2)
S1—C1—C6—C5172.14 (18)C3—C2—N2—O4−141.0 (2)
C4—C5—C6—C1−0.7 (4)C1—C2—N2—O438.4 (3)
O3—C7—C8—C956.4 (3)C7—N1—S1—O156.41 (17)
N1—C7—C8—C9−125.56 (19)C7—N1—S1—O2−175.07 (15)
O3—C7—C8—C13−122.1 (2)C7—N1—S1—C1−59.68 (17)
N1—C7—C8—C1356.0 (2)C6—C1—S1—O1−6.83 (18)
C13—C8—C9—C101.7 (3)C2—C1—S1—O1164.30 (16)
C7—C8—C9—C10−176.79 (18)C6—C1—S1—O2−136.91 (15)
C13—C8—C9—Cl1−176.28 (14)C2—C1—S1—O234.23 (18)
C7—C8—C9—Cl15.2 (2)C6—C1—S1—N1109.83 (16)
C8—C9—C10—C11−0.3 (3)C2—C1—S1—N1−79.04 (17)
Cl1—C9—C10—C11177.70 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.82 (1)2.13 (1)2.9465 (19)172 (2)
Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC13H9ClN2O5S
Mr340.73
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)12.266 (1), 12.643 (1), 18.738 (2)
V (Å3)2905.9 (5)
Z8
Radiation typeMo Kα
µ (mm−1)0.43
Crystal size (mm)0.48 × 0.40 × 0.20
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.820, 0.919
No. of measured, independent and
observed [I > 2σ(I)] reflections		7231, 2958, 2105
Rint0.015
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.096, 1.04
No. of reflections2958
No. of parameters202
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.23, −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···AD—HH···AD···AD—H···A
N1—H1N···O2i0.820 (14)2.131 (14)2.9465 (19)172.4 (19)
Symmetry code: (i) −x, −y+1, −z+1.
 

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

First citationBowes, 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
 First citationGowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2339.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Kozisek, J. & Fuess, H. (2006). Z. Naturforsch. Teil A, 61, 588–594.  CAS Google Scholar
 First citationGowda, B. T. & Mahadevappa, D. S. (1983). Talanta, 30, 359–362.  CrossRef PubMed CAS Web of Science Google Scholar
 First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113–120.  CAS Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSuchetan, P. A., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o244.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 2| February 2012| Page o274
doi:10.1107/S1600536811054882
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS