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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 66| Part 6| June 2010| Page o1253
https://doi.org/10.1107/S160053681001559X

4-Chloro-N-(4-chloro­benzo­yl)benzene­sulfonamide

P. A. Suchetan,a B. Thimme Gowda,a* Sabine Forob and Hartmut Fuessb

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 April 2010; accepted 27 April 2010; online 8 May 2010)

In the title compound, C13H9Cl2NO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. The mol­ecule is twisted at the S atom with a torsion angle of 67.5 (3)°. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 79.0 (1)° and that between the sulfonyl and benzoyl benzene rings is 85.6 (1)°. In the crystal, mol­ecules are linked by N—H⋯O(S) hydrogen bonds with graph-set descriptor C(4) along the [010] direction.

Related literature

For background literature and related structures, see: Gowda et al. (2009[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516.]); Suchetan et al. (2009[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, o3156.], 2010a[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o766.],b[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1040.]). 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

  • C13H9Cl2NO3S

  • Mr = 330.17

  • Orthorhombic, P b c a

  • a = 13.6405 (9) Å

  • b = 9.6495 (8) Å

  • c = 21.116 (2) Å

  • V = 2779.4 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.62 mm−1

  • T = 299 K

  • 0.34 × 0.30 × 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 = 0.816, Tmax = 0.886

  • 10651 measured reflections

  • 2550 independent reflections

  • 1946 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.102

  • S = 1.07

  • 2550 reflections

  • 184 parameters

  • 1 restraint

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

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O3i 0.85 (1) 2.23 (1) 3.074 (3) 172 (3)
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, 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/S160053681001559X/bx2279sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001559X/bx2279Isup2.hkl

checkCIF report


Comment top

As a part of studying the effect of ring and the side chain substituents on the crystal structures of N-aromatic sulfonamides(Gowda et al., 2009; Suchetan et al.,2009, 2010a,b), the structure of N-(4-chlorobenzoyl)-4-chlorobenzenesulfonamide (I) has been determined. The conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond (Fig.1), similar to those observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009), N-(4-chlorobenzoyl)-benzenesulfonamide (III)(Suchetan et al., 2009), N-(benzoyl)-4-chlorobenzenesulfonamide (IV) (Suchetan et al., 2010a) and N-(2-chlorobenzoyl)- 2-chlorobenzenesulfonamide (V)(Suchetan et al., 2010b).

The molecules are twisted at the S atoms with the torsional angles of 67.5 (3)°, compared to the values of -66.9 (3)° in (II), 69.4 (2)° in (III), -70.0 (2)°, 61.3 (2)° in the two independent molecules of (IV) and 66.5 (2)° in (V).

The dihedral angle between the sulfonyl and the benzoyl benzene rings is 85.6 (1)°, compared to the vlues of 80.3 (1) in (II), 68.6 (1)° in (III), 62.8 (1)° (molecule 1) and 78.6 (1)° (molecule 2) of (IV) and 76.9 (1)° in (V).

The molecules are linked by of N—H···O(S) hydrogen bonds with graph-set descriptor C(4) along [010] direction, ( Bernstein et al., 1995) (Table 1), Fig. 2.

Related literature top

For background literature and related structures, see: Gowda et al. (2009); Suchetan et al. (2009, 2010a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared by refluxing a mixture of 4-chlorobenzoic acid, 4-chlorobenzenesulfonamide and phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid 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.

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 later restrained to N—H = 0.86 (1) %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).

Structure description top

As a part of studying the effect of ring and the side chain substituents on the crystal structures of N-aromatic sulfonamides(Gowda et al., 2009; Suchetan et al.,2009, 2010a,b), the structure of N-(4-chlorobenzoyl)-4-chlorobenzenesulfonamide (I) has been determined. The conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond (Fig.1), similar to those observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009), N-(4-chlorobenzoyl)-benzenesulfonamide (III)(Suchetan et al., 2009), N-(benzoyl)-4-chlorobenzenesulfonamide (IV) (Suchetan et al., 2010a) and N-(2-chlorobenzoyl)- 2-chlorobenzenesulfonamide (V)(Suchetan et al., 2010b).

The molecules are twisted at the S atoms with the torsional angles of 67.5 (3)°, compared to the values of -66.9 (3)° in (II), 69.4 (2)° in (III), -70.0 (2)°, 61.3 (2)° in the two independent molecules of (IV) and 66.5 (2)° in (V).

The dihedral angle between the sulfonyl and the benzoyl benzene rings is 85.6 (1)°, compared to the vlues of 80.3 (1) in (II), 68.6 (1)° in (III), 62.8 (1)° (molecule 1) and 78.6 (1)° (molecule 2) of (IV) and 76.9 (1)° in (V).

The molecules are linked by of N—H···O(S) hydrogen bonds with graph-set descriptor C(4) along [010] direction, ( Bernstein et al., 1995) (Table 1), Fig. 2.

For background literature and related structures, see: Gowda et al. (2009); Suchetan et al. (2009, 2010a,b). 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 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.
4-Chloro-N-(4-chlorobenzoyl)benzenesulfonamide top
Crystal data top
C13H9Cl2NO3SF(000) = 1344
Mr = 330.17Dx = 1.578 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 6170 reflections
a = 13.6405 (9) Åθ = 2.6–27.9°
b = 9.6495 (8) ŵ = 0.62 mm−1
c = 21.116 (2) ÅT = 299 K
V = 2779.4 (4) Å3Prism, colourless
Z = 80.34 × 0.30 × 0.20 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2550 independent reflections
Radiation source: fine-focus sealed tube1946 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Rotation method data acquisition using ω and phi scansθmax = 25.3°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −15→16
Tmin = 0.816, Tmax = 0.886k = −11→8
10651 measured reflectionsl = −25→25
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0343P)2 + 2.7251P]
where P = (Fo2 + 2Fc2)/3
2550 reflections(Δ/σ)max = 0.004
184 parametersΔρmax = 0.22 e Å−3
1 restraintΔρmin = −0.44 e Å−3
Crystal data top
C13H9Cl2NO3SV = 2779.4 (4) Å3
Mr = 330.17Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 13.6405 (9) ŵ = 0.62 mm−1
b = 9.6495 (8) ÅT = 299 K
c = 21.116 (2) Å0.34 × 0.30 × 0.20 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2550 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		1946 reflections with I > 2σ(I)
Tmin = 0.816, Tmax = 0.886Rint = 0.026
10651 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0451 restraint
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.22 e Å−3
2550 reflectionsΔρmin = −0.44 e Å−3
184 parameters
Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C10.99158 (19)0.2323 (3)0.55735 (12)0.0379 (6)
C21.0488 (2)0.3501 (3)0.55627 (16)0.0589 (9)
H21.03050.42510.53130.071*
C31.1332 (2)0.3571 (3)0.59208 (17)0.0623 (9)
H31.17260.43580.59110.075*
C41.15804 (19)0.2462 (3)0.62912 (14)0.0453 (7)
C51.1027 (2)0.1281 (3)0.63045 (15)0.0532 (8)
H51.12140.05360.65560.064*
C61.0187 (2)0.1205 (3)0.59412 (14)0.0478 (7)
H60.98060.04060.59440.057*
C70.77151 (18)0.3738 (2)0.58811 (13)0.0358 (6)
C80.68782 (18)0.3726 (2)0.63338 (13)0.0361 (6)
C90.6890 (2)0.4687 (3)0.68266 (14)0.0450 (7)
H90.74060.53130.68580.054*
C100.6147 (2)0.4719 (3)0.72667 (14)0.0504 (7)
H100.61620.53580.75960.061*
C110.5378 (2)0.3794 (3)0.72143 (14)0.0464 (7)
C120.5335 (2)0.2852 (3)0.67218 (15)0.0482 (7)
H120.48050.22520.66840.058*
C130.60898 (18)0.2814 (3)0.62879 (14)0.0431 (7)
H130.60720.21710.59600.052*
N10.79169 (16)0.2491 (2)0.55934 (11)0.0395 (5)
H1N0.7586 (18)0.1768 (19)0.5681 (13)0.047*
O10.87074 (15)0.0780 (2)0.49305 (11)0.0610 (6)
O20.88803 (15)0.3255 (2)0.46352 (9)0.0595 (6)
O30.82124 (13)0.47670 (18)0.57873 (10)0.0485 (5)
Cl11.26227 (6)0.25736 (10)0.67639 (4)0.0679 (3)
Cl20.44389 (6)0.38508 (11)0.77714 (4)0.0710 (3)
S10.88532 (5)0.21948 (7)0.51034 (3)0.0437 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0323 (13)0.0400 (15)0.0415 (15)0.0010 (11)0.0068 (12)−0.0043 (13)
C20.0546 (19)0.0498 (18)0.072 (2)−0.0097 (15)−0.0159 (17)0.0228 (16)
C30.0489 (18)0.0569 (19)0.081 (2)−0.0157 (15)−0.0158 (17)0.0160 (18)
C40.0324 (13)0.0561 (17)0.0474 (16)0.0058 (13)0.0016 (13)−0.0011 (14)
C50.0475 (17)0.0484 (17)0.064 (2)0.0084 (14)0.0035 (15)0.0128 (15)
C60.0418 (16)0.0391 (15)0.0624 (19)−0.0035 (13)0.0076 (14)0.0040 (14)
C70.0299 (13)0.0294 (13)0.0482 (16)0.0023 (11)−0.0065 (11)−0.0014 (12)
C80.0308 (13)0.0295 (13)0.0480 (16)0.0057 (10)−0.0052 (12)−0.0011 (12)
C90.0364 (15)0.0432 (15)0.0555 (18)−0.0008 (13)−0.0073 (13)−0.0093 (14)
C100.0463 (17)0.0595 (19)0.0454 (17)0.0041 (15)−0.0051 (14)−0.0129 (15)
C110.0368 (15)0.0548 (18)0.0475 (17)0.0106 (13)0.0015 (13)0.0041 (15)
C120.0360 (15)0.0419 (16)0.067 (2)−0.0017 (12)0.0044 (14)−0.0003 (15)
C130.0357 (14)0.0327 (14)0.0608 (18)0.0006 (12)0.0007 (14)−0.0091 (13)
N10.0327 (12)0.0294 (11)0.0564 (15)−0.0013 (9)0.0065 (11)−0.0053 (11)
O10.0491 (12)0.0582 (13)0.0758 (15)0.0005 (10)0.0050 (11)−0.0327 (12)
O20.0550 (13)0.0814 (15)0.0421 (11)−0.0084 (12)−0.0030 (10)0.0079 (11)
O30.0399 (10)0.0333 (10)0.0721 (14)−0.0061 (9)0.0041 (10)−0.0047 (10)
Cl10.0442 (4)0.0885 (6)0.0709 (6)0.0080 (4)−0.0124 (4)0.0004 (5)
Cl20.0533 (5)0.1024 (7)0.0574 (5)0.0095 (5)0.0137 (4)0.0039 (5)
S10.0380 (4)0.0479 (4)0.0452 (4)−0.0015 (3)0.0034 (3)−0.0091 (3)
Geometric parameters (Å, º) top
C1—C21.379 (4)C8—C131.393 (3)
C1—C61.380 (4)C8—C91.394 (4)
C1—S11.761 (3)C9—C101.376 (4)
C2—C31.379 (4)C9—H90.9300
C2—H20.9300C10—C111.381 (4)
C3—C41.368 (4)C10—H100.9300
C3—H30.9300C11—C121.383 (4)
C4—C51.367 (4)C11—Cl21.740 (3)
C4—Cl11.740 (3)C12—C131.379 (4)
C5—C61.380 (4)C12—H120.9300
C5—H50.9300C13—H130.9300
C6—H60.9300N1—S11.668 (2)
C7—O31.219 (3)N1—H1N0.851 (10)
C7—N11.376 (3)O1—S11.427 (2)
C7—C81.489 (4)O2—S11.423 (2)
C2—C1—C6120.1 (3)C10—C9—C8120.7 (3)
C2—C1—S1121.0 (2)C10—C9—H9119.7
C6—C1—S1118.9 (2)C8—C9—H9119.6
C3—C2—C1120.3 (3)C9—C10—C11119.4 (3)
C3—C2—H2119.9C9—C10—H10120.3
C1—C2—H2119.9C11—C10—H10120.3
C4—C3—C2118.8 (3)C12—C11—C10121.1 (3)
C4—C3—H3120.6C12—C11—Cl2119.9 (2)
C2—C3—H3120.6C10—C11—Cl2119.0 (2)
C3—C4—C5121.8 (3)C13—C12—C11119.1 (3)
C3—C4—Cl1118.8 (2)C13—C12—H12120.5
C5—C4—Cl1119.4 (2)C11—C12—H12120.5
C4—C5—C6119.4 (3)C12—C13—C8120.9 (3)
C4—C5—H5120.3C12—C13—H13119.6
C6—C5—H5120.3C8—C13—H13119.6
C5—C6—C1119.6 (3)C7—N1—S1125.21 (18)
C5—C6—H6120.2C7—N1—H1N121 (2)
C1—C6—H6120.2S1—N1—H1N113.7 (19)
O3—C7—N1122.0 (2)O2—S1—O1120.90 (14)
O3—C7—C8122.5 (2)O2—S1—N1109.13 (12)
N1—C7—C8115.5 (2)O1—S1—N1102.45 (12)
C13—C8—C9118.8 (3)O2—S1—C1108.63 (12)
C13—C8—C7123.5 (2)O1—S1—C1109.05 (13)
C9—C8—C7117.7 (2)N1—S1—C1105.57 (12)
C6—C1—C2—C3−0.3 (5)C9—C10—C11—Cl2−179.7 (2)
S1—C1—C2—C3−178.3 (3)C10—C11—C12—C131.9 (4)
C1—C2—C3—C4−0.9 (5)Cl2—C11—C12—C13−179.5 (2)
C2—C3—C4—C51.4 (5)C11—C12—C13—C8−1.3 (4)
C2—C3—C4—Cl1−177.8 (3)C9—C8—C13—C12−0.3 (4)
C3—C4—C5—C6−0.8 (5)C7—C8—C13—C12180.0 (2)
Cl1—C4—C5—C6178.5 (2)O3—C7—N1—S11.5 (4)
C4—C5—C6—C1−0.4 (4)C8—C7—N1—S1−175.99 (18)
C2—C1—C6—C50.9 (4)C7—N1—S1—O2−49.1 (3)
S1—C1—C6—C5179.0 (2)C7—N1—S1—O1−178.3 (2)
O3—C7—C8—C13154.8 (3)C7—N1—S1—C167.5 (2)
N1—C7—C8—C13−27.7 (4)C2—C1—S1—O215.4 (3)
O3—C7—C8—C9−24.9 (4)C6—C1—S1—O2−162.6 (2)
N1—C7—C8—C9152.5 (2)C2—C1—S1—O1149.0 (3)
C13—C8—C9—C101.2 (4)C6—C1—S1—O1−29.0 (3)
C7—C8—C9—C10−179.1 (2)C2—C1—S1—N1−101.5 (3)
C8—C9—C10—C11−0.5 (4)C6—C1—S1—N180.5 (2)
C9—C10—C11—C12−1.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.85 (1)2.23 (1)3.074 (3)172 (3)
Symmetry code: (i) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formulaC13H9Cl2NO3S
Mr330.17
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)299
a, b, c (Å)13.6405 (9), 9.6495 (8), 21.116 (2)
V (Å3)2779.4 (4)
Z8
Radiation typeMo Kα
µ (mm−1)0.62
Crystal size (mm)0.34 × 0.30 × 0.20
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.816, 0.886
No. of measured, independent and
observed [I > 2σ(I)] reflections		10651, 2550, 1946
Rint0.026
(sin θ/λ)max (Å−1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.102, 1.07
No. of reflections2550
No. of parameters184
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.22, −0.44

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXL97(Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.851 (10)2.228 (11)3.074 (3)172 (3)
Symmetry code: (i) −x+3/2, y−1/2, z.
 

Acknowledgements

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

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 citationGowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516.  Web of Science CSD CrossRef IUCr Journals 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 citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSuchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, o3156.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSuchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o766.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSuchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1040.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 66| Part 6| June 2010| Page o1253
https://doi.org/10.1107/S160053681001559X
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