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 67| Part 1| January 2011| Page o232
https://doi.org/10.1107/S1600536810053638

4-Chloro-N-(2,3-di­chloro­phen­yl)benzene­sulfonamide

K. Shakuntala,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 21 December 2010; accepted 21 December 2010; online 24 December 2010)

In the title compound, C12H8Cl3NO2S, the two aromatic rings are tilted relative to each other by 56.5 (1)°. The crystal structure features centrosymmetric dimers in which mol­ecules are linked by N—H⋯O hydrogen bonds.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2010[Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o1283.]); Nirmala et al. (2010[Nirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o3060.]); Shakuntala et al. (2010[Shakuntala, K., Foro, S., Gowda, B. T., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o3062.]). For related structures, see: Gelbrich et al. (2007[Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.]); Perlovich et al. (2006[Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780-o782.]).

[Scheme 1]

Experimental

Crystal data

  • C12H8Cl3NO2S

  • Mr = 336.60

  • Monoclinic, P 21 /c

  • a = 7.224 (1) Å

  • b = 14.975 (2) Å

  • c = 13.170 (2) Å

  • β = 97.16 (1)°

  • V = 1413.6 (3) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 7.23 mm−1

  • T = 299 K

  • 0.38 × 0.30 × 0.20 mm
Data collection

  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.170, Tmax = 0.326

  • 2767 measured reflections

  • 2516 independent reflections

  • 2277 reflections with I > 2σ(I)

  • Rint = 0.062

  • 3 standard reflections every 120 min intensity decay: 0.5%
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.137

  • S = 1.15

  • 2516 reflections

  • 176 parameters

  • 1 restraint

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

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.51 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1i 0.86 (2) 2.11 (2) 2.944 (3) 163 (3)
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: CAD-4-PC (Enraf–Nonius, 1996[Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987[Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.]); 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: https://doi.org/10.1107/S1600536810053638/bt5445sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810053638/bt5445Isup2.hkl

checkCIF report


Comment top

As part of a study of the substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2010; Nirmala et al., 2010; Shakuntala et al., 2010), in the present work, the structure of 4-chloro-N-(2,3-dichlorophenyl)-benzenesulfonamide (I) has been determined. The conformation of the N—C bond in the C—SO2—NH—C segment of the structure has gauche torsions with respect to the S═ O bonds (Fig. 1). The molecule is bent at the S atom with the C—SO2—NH—C torsion angle of -56.7 (2)°, compared to the values of 65.4 (2) and -61.7 (2) in the two molecules of N-(2,3-dichlorophenyl)- 4-methylbenzenesulfonamide (II) (Shakuntala et al., 2010). The conformations of the N—H bond and the ortho-chloro group in the anilino benzene ring are syn to each other.

The sulfonyl and the anilino benzene rings in (I) are tilted relative to each other by 56.5 (1)°, compared to the values of 76.0 (1)° (molecule 1) and 79.9 (1)° (molecule 2) in (II).

The other bond parameters in (I) are similar to those observed in (II), N-(2,3-dichlorophenyl)-2,4-dimethylbenzenesulfonamide (Nirmala et al., 2010), N-(3,4-dimethylphenyl)-4-chlorobenzene- sulfonamide (Gowda et al., 2010) and other aryl sulfonamides, (Perlovich et al., 2006; Gelbrich et al., 2007).

The structure shows N—H···O intermolecular H-bonding (Table 1). The crystal packing is shown in Fig. 2.

Related literature top

For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2010); Nirmala et al. (2010); Shakuntala et al. (2010). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

The solution of chlorobenzene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 4-chlorobenzenesulfonylchloride was treated with 2,3-dichloroaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant 4-chloro-N-(2,3-dichlorophenyl)- benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra.

Prism like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Refinement top

The H atom of the NH group was located in a diffrerence and its coordinates were refined with the N—H distance restrained to 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model [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.

Structure description top

As part of a study of the substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2010; Nirmala et al., 2010; Shakuntala et al., 2010), in the present work, the structure of 4-chloro-N-(2,3-dichlorophenyl)-benzenesulfonamide (I) has been determined. The conformation of the N—C bond in the C—SO2—NH—C segment of the structure has gauche torsions with respect to the S═ O bonds (Fig. 1). The molecule is bent at the S atom with the C—SO2—NH—C torsion angle of -56.7 (2)°, compared to the values of 65.4 (2) and -61.7 (2) in the two molecules of N-(2,3-dichlorophenyl)- 4-methylbenzenesulfonamide (II) (Shakuntala et al., 2010). The conformations of the N—H bond and the ortho-chloro group in the anilino benzene ring are syn to each other.

The sulfonyl and the anilino benzene rings in (I) are tilted relative to each other by 56.5 (1)°, compared to the values of 76.0 (1)° (molecule 1) and 79.9 (1)° (molecule 2) in (II).

The other bond parameters in (I) are similar to those observed in (II), N-(2,3-dichlorophenyl)-2,4-dimethylbenzenesulfonamide (Nirmala et al., 2010), N-(3,4-dimethylphenyl)-4-chlorobenzene- sulfonamide (Gowda et al., 2010) and other aryl sulfonamides, (Perlovich et al., 2006; Gelbrich et al., 2007).

The structure shows N—H···O intermolecular H-bonding (Table 1). The crystal packing is shown in Fig. 2.

For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2010); Nirmala et al. (2010); Shakuntala et al. (2010). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); 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 and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
4-Chloro-N-(2,3-dichlorophenyl)benzenesulfonamide top
Crystal data top
C12H8Cl3NO2SF(000) = 680
Mr = 336.60Dx = 1.582 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 7.224 (1) Åθ = 6.8–22.5°
b = 14.975 (2) ŵ = 7.23 mm−1
c = 13.170 (2) ÅT = 299 K
β = 97.16 (1)°Prism, colourless
V = 1413.6 (3) Å30.38 × 0.30 × 0.20 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		2277 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
Graphite monochromatorθmax = 66.9°, θmin = 4.5°
ω/2θ scansh = −8→8
Absorption correction: ψ scan
(North et al., 1968)		k = −17→0
Tmin = 0.170, Tmax = 0.326l = −15→1
2767 measured reflections3 standard reflections every 120 min
2516 independent reflections intensity decay: 0.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137 w = 1/[σ2(Fo2) + (0.0763P)2 + 1.0223P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.001
2516 reflectionsΔρmax = 0.46 e Å−3
176 parametersΔρmin = −0.51 e Å−3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0074 (7)
Crystal data top
C12H8Cl3NO2SV = 1413.6 (3) Å3
Mr = 336.60Z = 4
Monoclinic, P21/cCu Kα radiation
a = 7.224 (1) ŵ = 7.23 mm−1
b = 14.975 (2) ÅT = 299 K
c = 13.170 (2) Å0.38 × 0.30 × 0.20 mm
β = 97.16 (1)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		2277 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.062
Tmin = 0.170, Tmax = 0.3263 standard reflections every 120 min
2767 measured reflections intensity decay: 0.5%
2516 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0431 restraint
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.15Δρmax = 0.46 e Å−3
2516 reflectionsΔρmin = −0.51 e Å−3
176 parameters
Special details top

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
C10.5255 (4)0.83900 (18)0.1877 (2)0.0332 (6)
C20.4733 (4)0.80016 (19)0.2749 (2)0.0372 (6)
H20.35020.80340.28860.045*
C30.6057 (4)0.7565 (2)0.3415 (2)0.0401 (7)
H30.57260.73030.40080.048*
C40.7869 (4)0.7519 (2)0.3199 (2)0.0429 (7)
C50.8394 (5)0.7896 (3)0.2323 (3)0.0551 (9)
H50.96220.78530.21830.066*
C60.7079 (5)0.8336 (2)0.1657 (3)0.0504 (8)
H60.74120.85940.10640.060*
C70.3738 (4)1.03085 (17)0.2425 (2)0.0326 (6)
C80.5279 (4)1.06989 (18)0.3008 (2)0.0345 (6)
C90.5110 (5)1.10001 (19)0.3994 (2)0.0416 (7)
C100.3474 (5)1.0888 (2)0.4403 (3)0.0516 (8)
H100.33831.10760.50680.062*
C110.1954 (5)1.0497 (2)0.3829 (3)0.0536 (8)
H110.08441.04220.41090.064*
C120.2082 (4)1.0217 (2)0.2843 (2)0.0431 (7)
H120.10500.99640.24550.052*
N10.3873 (3)1.00439 (16)0.14018 (17)0.0365 (6)
H1N0.467 (4)1.031 (2)0.107 (2)0.044*
O10.4094 (4)0.89646 (15)0.00411 (15)0.0486 (6)
O20.1801 (3)0.87121 (16)0.12563 (17)0.0469 (5)
Cl10.95260 (14)0.69893 (7)0.40587 (8)0.0675 (3)
Cl20.73258 (11)1.08276 (6)0.24909 (6)0.0517 (3)
Cl30.69792 (14)1.15158 (6)0.47020 (6)0.0596 (3)
S10.35957 (10)0.89965 (5)0.10606 (5)0.0353 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0408 (15)0.0311 (13)0.0289 (13)−0.0055 (11)0.0092 (11)−0.0026 (10)
C20.0421 (15)0.0385 (15)0.0334 (14)−0.0047 (12)0.0137 (12)−0.0011 (11)
C30.0514 (17)0.0388 (15)0.0309 (14)−0.0032 (13)0.0085 (12)0.0011 (11)
C40.0419 (16)0.0372 (15)0.0479 (18)−0.0019 (12)−0.0004 (13)−0.0040 (12)
C50.0352 (16)0.064 (2)0.067 (2)−0.0019 (15)0.0126 (15)0.0076 (17)
C60.0483 (18)0.059 (2)0.0478 (18)−0.0058 (15)0.0201 (15)0.0102 (15)
C70.0400 (14)0.0281 (12)0.0303 (13)0.0033 (11)0.0068 (11)0.0040 (10)
C80.0387 (15)0.0308 (13)0.0343 (14)0.0054 (11)0.0055 (11)0.0045 (11)
C90.0533 (18)0.0326 (14)0.0377 (16)0.0021 (13)0.0014 (13)−0.0018 (11)
C100.066 (2)0.0518 (19)0.0397 (17)0.0027 (16)0.0189 (15)−0.0070 (13)
C110.056 (2)0.056 (2)0.0528 (19)−0.0010 (16)0.0256 (16)−0.0040 (15)
C120.0419 (16)0.0428 (16)0.0460 (17)0.0003 (13)0.0111 (13)−0.0012 (13)
N10.0441 (13)0.0362 (13)0.0302 (12)−0.0057 (10)0.0082 (10)0.0030 (9)
O10.0695 (15)0.0514 (13)0.0254 (10)−0.0129 (11)0.0077 (10)−0.0030 (8)
O20.0413 (12)0.0525 (13)0.0460 (12)−0.0151 (10)0.0019 (9)0.0011 (10)
Cl10.0594 (6)0.0690 (6)0.0686 (6)0.0082 (4)−0.0138 (4)0.0057 (4)
Cl20.0380 (4)0.0687 (6)0.0490 (5)−0.0056 (3)0.0081 (3)−0.0070 (3)
Cl30.0697 (6)0.0598 (5)0.0456 (5)−0.0055 (4)−0.0068 (4)−0.0122 (3)
S10.0418 (4)0.0381 (4)0.0260 (4)−0.0093 (3)0.0045 (3)−0.0011 (2)
Geometric parameters (Å, º) top
C1—C21.381 (4)C7—N11.420 (3)
C1—C61.386 (4)C8—C91.394 (4)
C1—S11.760 (3)C8—Cl21.714 (3)
C2—C31.379 (4)C9—C101.369 (5)
C2—H20.9300C9—Cl31.724 (3)
C3—C41.376 (4)C10—C111.384 (5)
C3—H30.9300C10—H100.9300
C4—C51.380 (5)C11—C121.379 (4)
C4—Cl11.734 (3)C11—H110.9300
C5—C61.378 (5)C12—H120.9300
C5—H50.9300N1—S11.637 (2)
C6—H60.9300N1—H1N0.858 (18)
C7—C121.384 (4)O1—S11.434 (2)
C7—C81.399 (4)O2—S11.418 (2)
C2—C1—C6121.0 (3)C7—C8—Cl2119.7 (2)
C2—C1—S1119.3 (2)C10—C9—C8120.4 (3)
C6—C1—S1119.7 (2)C10—C9—Cl3119.9 (2)
C3—C2—C1119.3 (3)C8—C9—Cl3119.7 (2)
C3—C2—H2120.4C9—C10—C11120.1 (3)
C1—C2—H2120.4C9—C10—H10119.9
C4—C3—C2119.6 (3)C11—C10—H10119.9
C4—C3—H3120.2C12—C11—C10120.1 (3)
C2—C3—H3120.2C12—C11—H11120.0
C3—C4—C5121.4 (3)C10—C11—H11120.0
C3—C4—Cl1119.0 (2)C11—C12—C7120.5 (3)
C5—C4—Cl1119.6 (2)C11—C12—H12119.8
C6—C5—C4119.2 (3)C7—C12—H12119.8
C6—C5—H5120.4C7—N1—S1120.50 (18)
C4—C5—H5120.4C7—N1—H1N118 (2)
C5—C6—C1119.5 (3)S1—N1—H1N112 (2)
C5—C6—H6120.2O2—S1—O1120.13 (14)
C1—C6—H6120.2O2—S1—N1108.73 (14)
C12—C7—C8119.4 (3)O1—S1—N1104.63 (12)
C12—C7—N1120.9 (3)O2—S1—C1107.60 (13)
C8—C7—N1119.6 (2)O1—S1—C1108.90 (14)
C9—C8—C7119.4 (3)N1—S1—C1106.03 (13)
C9—C8—Cl2120.9 (2)
C6—C1—C2—C30.9 (4)C8—C9—C10—C11−1.8 (5)
S1—C1—C2—C3−176.7 (2)Cl3—C9—C10—C11178.3 (3)
C1—C2—C3—C4−0.4 (4)C9—C10—C11—C120.0 (5)
C2—C3—C4—C5−0.5 (5)C10—C11—C12—C71.3 (5)
C2—C3—C4—Cl1178.6 (2)C8—C7—C12—C11−0.8 (4)
C3—C4—C5—C60.7 (5)N1—C7—C12—C11−178.4 (3)
Cl1—C4—C5—C6−178.3 (3)C12—C7—N1—S1−63.5 (3)
C4—C5—C6—C1−0.1 (6)C8—C7—N1—S1118.9 (2)
C2—C1—C6—C5−0.7 (5)C7—N1—S1—O258.7 (2)
S1—C1—C6—C5177.0 (3)C7—N1—S1—O1−171.8 (2)
C12—C7—C8—C9−0.9 (4)C7—N1—S1—C1−56.7 (2)
N1—C7—C8—C9176.7 (2)C2—C1—S1—O2−20.9 (3)
C12—C7—C8—Cl2−179.2 (2)C6—C1—S1—O2161.3 (2)
N1—C7—C8—Cl2−1.6 (3)C2—C1—S1—O1−152.6 (2)
C7—C8—C9—C102.2 (4)C6—C1—S1—O129.6 (3)
Cl2—C8—C9—C10−179.5 (2)C2—C1—S1—N195.3 (2)
C7—C8—C9—Cl3−177.8 (2)C6—C1—S1—N1−82.5 (3)
Cl2—C8—C9—Cl30.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.86 (2)2.11 (2)2.944 (3)163 (3)
Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formulaC12H8Cl3NO2S
Mr336.60
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)7.224 (1), 14.975 (2), 13.170 (2)
β (°) 97.16 (1)
V (Å3)1413.6 (3)
Z4
Radiation typeCu Kα
µ (mm−1)7.23
Crystal size (mm)0.38 × 0.30 × 0.20
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.170, 0.326
No. of measured, independent and
observed [I > 2σ(I)] reflections		2767, 2516, 2277
Rint0.062
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.137, 1.15
No. of reflections2516
No. of parameters176
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.46, −0.51

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), 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···O1i0.858 (18)2.11 (2)2.944 (3)163 (3)
Symmetry code: (i) −x+1, −y+2, −z.
 

Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

First citationEnraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
 First citationGelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o1283.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationNirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o3060.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
 First citationPerlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780–o782.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationShakuntala, K., Foro, S., Gowda, B. T., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o3062.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationStoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.  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 67| Part 1| January 2011| Page o232
https://doi.org/10.1107/S1600536810053638
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