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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 o142
https://doi.org/10.1107/S1600536810051792

N-(2,6-Di­chloro­phen­yl)-4-methyl­benzene­sulfonamide

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 4 December 2010; accepted 10 December 2010; online 15 December 2010)

In the title compound, C13H11Cl2NO2S, the mol­ecule is bent at the S atom with a C—SO2—NH—C torsion angle of −90.4 (2)°. The sulfonyl benzene and the aniline benzene rings are tilted relative to each other by 51.7 (1)°. In the crystal, mol­ecules are linked by N— H⋯O inter­actions into chains with graph-set notation C(4) along [100].

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009[Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2009). Acta Cryst. E65, o2334.]); Nirmala et al. (2010[Nirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1168.]); 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.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C13H11Cl2NO2S

  • Mr = 316.19

  • Monoclinic, P 21 /n

  • a = 5.0456 (6) Å

  • b = 17.128 (2) Å

  • c = 16.540 (2) Å

  • β = 97.13 (1)°

  • V = 1418.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.60 mm−1

  • T = 293 K

  • 0.55 × 0.28 × 0.25 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 = 0.734, Tmax = 0.864

  • 5631 measured reflections

  • 2904 independent reflections

  • 2493 reflections with I > 2σ(I)

  • Rint = 0.011
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.102

  • S = 1.05

  • 2904 reflections

  • 176 parameters

  • 1 restraint

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

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.48 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1i 0.83 (2) 2.16 (2) 2.971 (2) 165 (2)
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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/S1600536810051792/bx2335sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051792/bx2335Isup2.hkl

checkCIF report


Comment top

In the present work, as part of a study of the substituent effects on the crystal structures of N-(aryl)arylsulfonamides (Gowda et al., 2009; Nirmala et al., 2010; Shakuntala et al., 2010), the structure of N-(2,6-dichlorophenyl)-4-methylbenzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond orients away from the two ortho-chloro groups in the adjacent benzene ring.

The molecule in (I) is bent at the S atom with the C—SO2—NH—C torsion angle of -90.4 (2)°, compared to the values of 88.0 (2)° in N-(2,6-dimethylphenyl)-4-methylbenzenesulfonamide (II) (Nirmala et al., 2010), 65.4 (2)° (molecule 1) and -61.7 (2)° (molecule 2) in N-(2,3-dichlorophenyl)-4-methylbenzenesulfonamide (III) (Shakuntala et al., 2010) and 69.3 (4)° in N-(3,5-dichlorophenyl)-4-methylbenzenesulfonamide (IV) (Gowda et al., 2009).

The two benzene rings in (I) are tilted relative to each other by 51.7 (1)°, compared to the values of 49.8 (1)° in (II). 76.0 (1)° (molecule 1) and 79.9 (1)° (molecule 2) in (III) and 79.6 (1)° in (IV).

The other bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal, molecules are linked by N— H··· O interaction into chain with graph-set notation C(4) along [100] (Bernstein et al., 1995), Fig. 2.

Related literature top

For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009); Nirmala et al. (2010); Shakuntala et al. (2010). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The solution of toluene (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-methylbenzenesulfonylchloride was treated with 2,6-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 N-(2,6-dichlorophenyl)-4-methylbenzenesulfonamide 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.

Rod like colourless 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 difference map and later restrained to the distance N—H = 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.96 Å H-atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Structure description top

In the present work, as part of a study of the substituent effects on the crystal structures of N-(aryl)arylsulfonamides (Gowda et al., 2009; Nirmala et al., 2010; Shakuntala et al., 2010), the structure of N-(2,6-dichlorophenyl)-4-methylbenzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond orients away from the two ortho-chloro groups in the adjacent benzene ring.

The molecule in (I) is bent at the S atom with the C—SO2—NH—C torsion angle of -90.4 (2)°, compared to the values of 88.0 (2)° in N-(2,6-dimethylphenyl)-4-methylbenzenesulfonamide (II) (Nirmala et al., 2010), 65.4 (2)° (molecule 1) and -61.7 (2)° (molecule 2) in N-(2,3-dichlorophenyl)-4-methylbenzenesulfonamide (III) (Shakuntala et al., 2010) and 69.3 (4)° in N-(3,5-dichlorophenyl)-4-methylbenzenesulfonamide (IV) (Gowda et al., 2009).

The two benzene rings in (I) are tilted relative to each other by 51.7 (1)°, compared to the values of 49.8 (1)° in (II). 76.0 (1)° (molecule 1) and 79.9 (1)° (molecule 2) in (III) and 79.6 (1)° in (IV).

The other bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal, molecules are linked by N— H··· O interaction into chain with graph-set notation C(4) along [100] (Bernstein et al., 1995), Fig. 2.

For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009); Nirmala et al. (2010); Shakuntala et al. (2010). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006). For hydrogen-bond motifs, see: Bernstein et al. (1995).

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
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
N-(2,6-Dichlorophenyl)-4-methylbenzenesulfonamide top
Crystal data top
C13H11Cl2NO2SF(000) = 648
Mr = 316.19Dx = 1.481 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3098 reflections
a = 5.0456 (6) Åθ = 3.4–27.7°
b = 17.128 (2) ŵ = 0.60 mm−1
c = 16.540 (2) ÅT = 293 K
β = 97.13 (1)°Rod, colourless
V = 1418.4 (3) Å30.55 × 0.28 × 0.25 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2904 independent reflections
Radiation source: fine-focus sealed tube2493 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
Rotation method data acquisition using ω and phi scansθmax = 26.4°, θmin = 3.4°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −3→6
Tmin = 0.734, Tmax = 0.864k = −21→18
5631 measured reflectionsl = −20→15
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0469P)2 + 0.7136P]
where P = (Fo2 + 2Fc2)/3
2904 reflections(Δ/σ)max = 0.028
176 parametersΔρmax = 0.30 e Å−3
1 restraintΔρmin = −0.48 e Å−3
Crystal data top
C13H11Cl2NO2SV = 1418.4 (3) Å3
Mr = 316.19Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.0456 (6) ŵ = 0.60 mm−1
b = 17.128 (2) ÅT = 293 K
c = 16.540 (2) Å0.55 × 0.28 × 0.25 mm
β = 97.13 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2904 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		2493 reflections with I > 2σ(I)
Tmin = 0.734, Tmax = 0.864Rint = 0.011
5631 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.30 e Å−3
2904 reflectionsΔρmin = −0.48 e Å−3
176 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
C10.0019 (4)0.70942 (11)0.33030 (12)0.0361 (4)
C2−0.2076 (4)0.76146 (13)0.32461 (14)0.0471 (5)
H2−0.32800.76450.27730.057*
C3−0.2359 (5)0.80913 (14)0.39037 (16)0.0559 (6)
H3−0.37840.84390.38690.067*
C4−0.0594 (5)0.80678 (14)0.46089 (15)0.0537 (6)
C50.1467 (5)0.75322 (15)0.46540 (15)0.0582 (6)
H50.26560.74980.51300.070*
C60.1799 (5)0.70457 (14)0.40068 (14)0.0508 (5)
H60.32020.66900.40450.061*
C7−0.0179 (4)0.50337 (11)0.28274 (13)0.0387 (4)
C80.1533 (5)0.45552 (13)0.24465 (16)0.0521 (6)
C90.2543 (6)0.38721 (15)0.2808 (2)0.0736 (8)
H90.37280.35700.25540.088*
C100.1807 (7)0.36409 (16)0.3536 (2)0.0793 (9)
H100.24880.31800.37760.095*
C110.0071 (6)0.40828 (15)0.39182 (17)0.0674 (7)
H11−0.04660.39170.44080.081*
C12−0.0877 (4)0.47785 (13)0.35667 (14)0.0471 (5)
C13−0.0895 (7)0.8623 (2)0.5296 (2)0.0855 (9)
H13A−0.26900.88190.52420.103*
H13B0.03280.90500.52780.103*
H13C−0.05130.83540.58070.103*
N1−0.1228 (3)0.57274 (10)0.24474 (10)0.0388 (4)
H1N−0.286 (3)0.5809 (14)0.2422 (14)0.047*
O10.3260 (3)0.63094 (9)0.25207 (10)0.0495 (4)
O2−0.0611 (3)0.69646 (9)0.17450 (9)0.0538 (4)
Cl10.23560 (17)0.47929 (4)0.14965 (5)0.0797 (3)
Cl2−0.30503 (14)0.53278 (4)0.40686 (4)0.0675 (2)
S10.05144 (9)0.65342 (3)0.24407 (3)0.03684 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0349 (9)0.0306 (9)0.0445 (10)−0.0027 (7)0.0116 (8)−0.0009 (8)
C20.0412 (11)0.0452 (12)0.0547 (12)0.0063 (9)0.0046 (9)−0.0015 (10)
C30.0526 (13)0.0481 (13)0.0695 (15)0.0120 (10)0.0170 (12)−0.0079 (11)
C40.0646 (14)0.0481 (12)0.0520 (13)−0.0031 (11)0.0211 (11)−0.0068 (10)
C50.0648 (15)0.0631 (15)0.0456 (12)0.0016 (12)0.0021 (10)−0.0030 (11)
C60.0508 (12)0.0485 (12)0.0526 (12)0.0097 (10)0.0045 (10)0.0011 (10)
C70.0349 (10)0.0309 (9)0.0502 (11)−0.0052 (8)0.0040 (8)−0.0045 (8)
C80.0499 (12)0.0367 (11)0.0716 (15)−0.0060 (9)0.0150 (11)−0.0127 (10)
C90.0655 (16)0.0384 (13)0.117 (3)0.0088 (12)0.0133 (16)−0.0165 (15)
C100.085 (2)0.0417 (14)0.105 (3)0.0090 (14)−0.0109 (18)0.0073 (15)
C110.0817 (18)0.0513 (14)0.0654 (16)−0.0093 (13)−0.0055 (13)0.0132 (12)
C120.0463 (12)0.0438 (11)0.0502 (12)−0.0056 (9)0.0021 (9)−0.0019 (9)
C130.104 (2)0.086 (2)0.0706 (18)0.0060 (19)0.0242 (17)−0.0281 (17)
N10.0267 (7)0.0374 (9)0.0524 (10)−0.0016 (7)0.0047 (7)−0.0004 (7)
O10.0310 (7)0.0471 (8)0.0728 (10)−0.0049 (6)0.0158 (7)−0.0143 (8)
O20.0686 (10)0.0477 (9)0.0462 (8)0.0004 (8)0.0111 (7)0.0086 (7)
Cl10.1007 (6)0.0582 (4)0.0912 (5)−0.0164 (4)0.0558 (4)−0.0252 (3)
Cl20.0720 (4)0.0775 (4)0.0574 (4)0.0006 (3)0.0258 (3)−0.0011 (3)
S10.0334 (2)0.0338 (3)0.0449 (3)−0.00172 (19)0.01091 (19)−0.00076 (19)
Geometric parameters (Å, º) top
C1—C21.377 (3)C8—Cl11.723 (3)
C1—C61.382 (3)C9—C101.363 (4)
C1—S11.7620 (19)C9—H90.9300
C2—C31.381 (3)C10—C111.370 (4)
C2—H20.9300C10—H100.9300
C3—C41.377 (4)C11—C121.385 (3)
C3—H30.9300C11—H110.9300
C4—C51.382 (3)C12—Cl21.733 (2)
C4—C131.504 (3)C13—H13A0.9600
C5—C61.383 (3)C13—H13B0.9600
C5—H50.9300C13—H13C0.9600
C6—H60.9300N1—S11.6386 (17)
C7—C121.385 (3)N1—H1N0.830 (16)
C7—C81.396 (3)O1—S11.4283 (14)
C7—N11.416 (3)O2—S11.4241 (16)
C8—C91.382 (4)
C2—C1—C6120.64 (19)C8—C9—H9119.9
C2—C1—S1118.80 (16)C9—C10—C11120.5 (3)
C6—C1—S1120.44 (15)C9—C10—H10119.8
C1—C2—C3118.8 (2)C11—C10—H10119.8
C1—C2—H2120.6C10—C11—C12119.3 (3)
C3—C2—H2120.6C10—C11—H11120.4
C4—C3—C2122.0 (2)C12—C11—H11120.4
C4—C3—H3119.0C7—C12—C11122.0 (2)
C2—C3—H3119.0C7—C12—Cl2119.81 (17)
C3—C4—C5117.9 (2)C11—C12—Cl2118.2 (2)
C3—C4—C13120.4 (2)C4—C13—H13A109.5
C5—C4—C13121.6 (3)C4—C13—H13B109.5
C4—C5—C6121.4 (2)H13A—C13—H13B109.5
C4—C5—H5119.3C4—C13—H13C109.5
C6—C5—H5119.3H13A—C13—H13C109.5
C1—C6—C5119.2 (2)H13B—C13—H13C109.5
C1—C6—H6120.4C7—N1—S1122.66 (13)
C5—C6—H6120.4C7—N1—H1N118.4 (17)
C12—C7—C8116.9 (2)S1—N1—H1N112.8 (17)
C12—C7—N1122.35 (18)O2—S1—O1119.96 (10)
C8—C7—N1120.7 (2)O2—S1—N1106.35 (9)
C9—C8—C7121.2 (3)O1—S1—N1106.68 (9)
C9—C8—Cl1118.5 (2)O2—S1—C1106.85 (10)
C7—C8—Cl1120.36 (19)O1—S1—C1107.77 (9)
C10—C9—C8120.1 (3)N1—S1—C1108.88 (9)
C10—C9—H9119.9
C6—C1—C2—C30.4 (3)C8—C7—C12—C110.1 (3)
S1—C1—C2—C3−175.68 (18)N1—C7—C12—C11177.3 (2)
C1—C2—C3—C40.8 (4)C8—C7—C12—Cl2−178.62 (16)
C2—C3—C4—C5−1.7 (4)N1—C7—C12—Cl2−1.4 (3)
C2—C3—C4—C13177.1 (3)C10—C11—C12—C71.7 (4)
C3—C4—C5—C61.5 (4)C10—C11—C12—Cl2−179.5 (2)
C13—C4—C5—C6−177.2 (3)C12—C7—N1—S1104.6 (2)
C2—C1—C6—C5−0.6 (3)C8—C7—N1—S1−78.4 (2)
S1—C1—C6—C5175.45 (18)C7—N1—S1—O2154.79 (16)
C4—C5—C6—C1−0.4 (4)C7—N1—S1—O125.65 (18)
C12—C7—C8—C9−2.0 (3)C7—N1—S1—C1−90.40 (17)
N1—C7—C8—C9−179.2 (2)C2—C1—S1—O225.70 (19)
C12—C7—C8—Cl1176.09 (16)C6—C1—S1—O2−150.40 (17)
N1—C7—C8—Cl1−1.1 (3)C2—C1—S1—O1155.87 (16)
C7—C8—C9—C102.1 (4)C6—C1—S1—O1−20.2 (2)
Cl1—C8—C9—C10−176.0 (2)C2—C1—S1—N1−88.79 (17)
C8—C9—C10—C11−0.2 (5)C6—C1—S1—N195.11 (18)
C9—C10—C11—C12−1.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.83 (2)2.16 (2)2.971 (2)165 (2)
Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC13H11Cl2NO2S
Mr316.19
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)5.0456 (6), 17.128 (2), 16.540 (2)
β (°) 97.13 (1)
V (Å3)1418.4 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.60
Crystal size (mm)0.55 × 0.28 × 0.25
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.734, 0.864
No. of measured, independent and
observed [I > 2σ(I)] reflections		5631, 2904, 2493
Rint0.011
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.102, 1.05
No. of reflections2904
No. of parameters176
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.30, −0.48

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···O1i0.830 (16)2.162 (17)2.971 (2)165 (2)
Symmetry code: (i) x−1, y, 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 citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science 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
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 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
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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.

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ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o142
https://doi.org/10.1107/S1600536810051792
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