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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 68| Part 7| July 2012| Page o2063
https://doi.org/10.1107/S1600536812024725

N,N-Bis(4-chloro­phenyl­sulfon­yl)succinamide dihydrate

H. Purandara,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 24 May 2012; accepted 30 May 2012; online 13 June 2012)

The asymmetric unit of the title compound, C16H14Cl2N2O6S2·2H2O, contains one half-mol­ecule of N,N-bis­(4-chloro­phenyl­sulfon­yl)succinamide, with a centre of symmetry at the mid-point of the central C—C bond, and one water mol­ecule. The succinamide mol­ecules are not directly connected via hydrogen bonds, but by hydrogen bonds via the water mol­ecules.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2000[Gowda, B. T., Kumar, B. H. A. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 721-728.]); Rodrigues et al. (2011[Rodrigues, V. Z., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o2179.]), of N-chloro­aryl­amides, see: Gowda & Rao (1989[Gowda, B. T. & Rao, P. J. M. (1989). Bull. Chem. Soc. Jpn, 62, 3303-3310.]); Jyothi & Gowda (2004[Jyothi, K. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 64-68.]) and of N-bromo­aryl­sulfonamides, see: Gowda & Mahadevappa (1983[Gowda, B. T. & Mahadevappa, D. S. (1983). Talanta, 30, 359-362.]); Usha & Gowda (2006[Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351-359.]).

[Scheme 1]

Experimental

Crystal data

  • C16H14Cl2N2O6S2·2H2O

  • Mr = 501.34

  • Monoclinic, C 2/c

  • a = 33.349 (2) Å

  • b = 4.9737 (4) Å

  • c = 13.171 (1) Å

  • β = 90.660 (7)°

  • V = 2184.5 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.53 mm−1

  • T = 293 K

  • 0.48 × 0.40 × 0.12 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 = 0.784, Tmax = 0.939

  • 3837 measured reflections

  • 2233 independent reflections

  • 1906 reflections with I > 2σ(I)

  • Rint = 0.012
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.120

  • S = 1.06

  • 2233 reflections

  • 139 parameters

  • 7 restraints

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

  • Δρmax = 0.55 e Å−3

  • Δρmin = −0.49 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O4i 0.84 (2) 1.90 (2) 2.735 (3) 178 (3)
O4—H41⋯O3 0.87 2.27 3.137 (4) 177
O4—H42⋯O2ii 0.84 2.23 2.941 (3) 142
O4—H42⋯O3ii 0.84 2.58 3.262 (4) 139
Symmetry codes: (i) [x, -y+1, z-{\script{1\over 2}}]; (ii) x, y+1, z.

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: https://doi.org/10.1107/S1600536812024725/bt5934sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024725/bt5934Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812024725/bt5934Isup3.cml

checkCIF report


Comment top

As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000; Rodrigues et al., 2011); N-chloroarylsulfonamides (Gowda & Rao, 1989; Jyothi & Gowda, 2004) and N-bromoaryl- sulfonamides (Gowda & Mahadevappa, 1983; Usha & Gowda, 2006), in the present work, the crystal structure of N,N-bis(4-chlorophenylsulfonyl)succinamide dihydrate has been determined (Fig. 1).

In the two C—SO2—NH—CO—CH2 central segments of the structure, the N—H, C=O and C—H bonds are anti to the adjacent bonds, similar to that observed in N,N-bis(4-chlorophenylsulfonyl)-adipamide (I) (Rodrigues et al., 2011). The orientations of sulfonamide groups with respect to the attached phenyl rings are given by the torsion angles of C2—C1—S1—N1 = 91.0 (2)° and C6—C1—S1—N1 = -87.6 (2)°. The molecule is bent at the S atom with the C1—S1—N1—C7 torsion angle of -70.0 (2)°, compared to the values of 55.0 (6)° in (I).

The dihedral angle between the benzene ring and the SO2—NH—C(O)—C segment in the two halves of the molecule is 78.0 (2)°, compared to the value of 83.5 (2)° in (I).

One of the water H-atoms exhibits bifurcated H-bonding with one of the O-atoms of SO2 group and the amide O-atom.

A series of N—H···O(W) and O–H···O(S and C) intermolecular hydrogen bonds (Table 1) link the molecules into infinite chains running along c-axis (Fig. 2).

Related literature top

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000); Rodrigues et al. (2011), of N-chloroarylamides, see: Gowda & Rao (1989); Jyothi & Gowda (2004) and of N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983); Usha & Gowda (2006).

Experimental top

Succinic anhydride (0.015 mole), N,N'-dicyclohexylcarbodiimide (0.01mole) and 4-dimethylaminopyridine (0.004 mole) were added to a solution of 4-chlorobenzenesulfonamide (0.01 mole) in dichloromethane. The mixture was strirred for 24 h at room temperature and set aside for completion of the reaction.. The reaction mixture was filtered to remove the by-product N,N'-dicyclohexylurea. The filtrate was diluted with water and then the organic layer was extracted. The latter was washed with water to remove the base and the succinic anhydride, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to dryness. The residue was recrystallized to constant melting point from ethyl acetate (163–165 °C). The purity of the compound was checked and characterized by its infrared spectrum.

Plate like colorless single crystals used in X-ray diffraction studies were grown in ethyl acetate solution by slow evaporation of the solvent from its solution at room temperature.

Refinement top

The H atoms of the water molecule were located in difference map and were refined as riding on their parent O atom. H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å, methylene C—H = 0.97 Å. All H atoms were refined with their isotropic displacement parameter set to 1.2 times of the Ueq of the parent atom. The amino H atom was freely refined with the N-H distance restrained to 0.86 (2)Å. The displacement ellipsoid of the water O atom was restrained to an isotropic bahaviour.

Structure description top

As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000; Rodrigues et al., 2011); N-chloroarylsulfonamides (Gowda & Rao, 1989; Jyothi & Gowda, 2004) and N-bromoaryl- sulfonamides (Gowda & Mahadevappa, 1983; Usha & Gowda, 2006), in the present work, the crystal structure of N,N-bis(4-chlorophenylsulfonyl)succinamide dihydrate has been determined (Fig. 1).

In the two C—SO2—NH—CO—CH2 central segments of the structure, the N—H, C=O and C—H bonds are anti to the adjacent bonds, similar to that observed in N,N-bis(4-chlorophenylsulfonyl)-adipamide (I) (Rodrigues et al., 2011). The orientations of sulfonamide groups with respect to the attached phenyl rings are given by the torsion angles of C2—C1—S1—N1 = 91.0 (2)° and C6—C1—S1—N1 = -87.6 (2)°. The molecule is bent at the S atom with the C1—S1—N1—C7 torsion angle of -70.0 (2)°, compared to the values of 55.0 (6)° in (I).

The dihedral angle between the benzene ring and the SO2—NH—C(O)—C segment in the two halves of the molecule is 78.0 (2)°, compared to the value of 83.5 (2)° in (I).

One of the water H-atoms exhibits bifurcated H-bonding with one of the O-atoms of SO2 group and the amide O-atom.

A series of N—H···O(W) and O–H···O(S and C) intermolecular hydrogen bonds (Table 1) link the molecules into infinite chains running along c-axis (Fig. 2).

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000); Rodrigues et al. (2011), of N-chloroarylamides, see: Gowda & Rao (1989); Jyothi & Gowda (2004) and of N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983); Usha & Gowda (2006).

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 with the displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
N,N-Bis(4-chlorophenylsulfonyl)succinamide dihydrate top
Crystal data top
C16H14Cl2N2O6S2·2H2OF(000) = 1032
Mr = 501.34Dx = 1.524 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1880 reflections
a = 33.349 (2) Åθ = 2.9–27.9°
b = 4.9737 (4) ŵ = 0.53 mm−1
c = 13.171 (1) ÅT = 293 K
β = 90.660 (7)°Plate, colourless
V = 2184.5 (3) Å30.48 × 0.40 × 0.12 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2233 independent reflections
Radiation source: fine-focus sealed tube1906 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
Rotation method data acquisition using ω and phi scansθmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −31→41
Tmin = 0.784, Tmax = 0.939k = −6→2
3837 measured reflectionsl = −16→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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0516P)2 + 3.9644P]
where P = (Fo2 + 2Fc2)/3
2233 reflections(Δ/σ)max = 0.004
139 parametersΔρmax = 0.55 e Å−3
7 restraintsΔρmin = −0.49 e Å−3
Crystal data top
C16H14Cl2N2O6S2·2H2OV = 2184.5 (3) Å3
Mr = 501.34Z = 4
Monoclinic, C2/cMo Kα radiation
a = 33.349 (2) ŵ = 0.53 mm−1
b = 4.9737 (4) ÅT = 293 K
c = 13.171 (1) Å0.48 × 0.40 × 0.12 mm
β = 90.660 (7)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2233 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		1906 reflections with I > 2σ(I)
Tmin = 0.784, Tmax = 0.939Rint = 0.012
3837 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0467 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.55 e Å−3
2233 reflectionsΔρmin = −0.49 e Å−3
139 parameters
Special details top

Experimental. Absorption correction: 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
Cl10.23218 (3)0.6607 (2)0.16525 (9)0.0914 (4)
S10.104840 (19)−0.08075 (14)−0.04102 (5)0.0398 (2)
O10.11860 (7)−0.1623 (5)−0.13839 (15)0.0590 (6)
O20.09204 (6)−0.2788 (4)0.02984 (15)0.0487 (5)
O30.04604 (6)0.1896 (4)0.09543 (13)0.0474 (5)
N10.06718 (7)0.1229 (5)−0.06616 (16)0.0398 (5)
H1N0.0665 (9)0.182 (6)−0.1257 (16)0.048*
C10.14188 (7)0.1197 (5)0.01713 (19)0.0388 (6)
C20.14276 (8)0.1472 (6)0.1219 (2)0.0480 (7)
H20.12450.05410.16160.058*
C30.17086 (9)0.3135 (7)0.1669 (2)0.0558 (8)
H30.17160.33460.23700.067*
C40.19760 (9)0.4469 (7)0.1072 (3)0.0565 (8)
C50.19727 (10)0.4182 (8)0.0030 (3)0.0700 (10)
H50.21580.5097−0.03630.084*
C60.16932 (10)0.2536 (7)−0.0421 (2)0.0584 (8)
H60.16880.2322−0.11230.070*
C70.04271 (7)0.2394 (5)0.00549 (19)0.0356 (5)
C80.01137 (7)0.4226 (6)−0.03950 (19)0.0401 (6)
H81−0.00740.3163−0.07940.048*
H820.02420.5487−0.08500.048*
O40.06513 (12)0.6735 (8)0.2409 (2)0.1206 (13)
H410.06060.53730.20140.145*
H420.07040.76330.18850.145*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0731 (6)0.0863 (7)0.1142 (9)−0.0383 (6)−0.0254 (6)0.0188 (6)
S10.0432 (4)0.0384 (4)0.0379 (3)0.0079 (3)0.0027 (2)−0.0028 (3)
O10.0674 (13)0.0645 (14)0.0451 (11)0.0189 (11)0.0070 (9)−0.0130 (10)
O20.0542 (12)0.0363 (10)0.0554 (12)−0.0005 (9)−0.0006 (9)0.0030 (9)
O30.0513 (11)0.0546 (12)0.0365 (10)0.0092 (9)0.0058 (8)0.0037 (9)
N10.0432 (12)0.0440 (13)0.0322 (10)0.0089 (10)−0.0001 (9)−0.0004 (9)
C10.0340 (12)0.0399 (14)0.0425 (13)0.0055 (11)0.0039 (10)0.0063 (11)
C20.0418 (14)0.0598 (18)0.0424 (14)−0.0101 (13)0.0040 (11)0.0073 (13)
C30.0507 (16)0.067 (2)0.0496 (16)−0.0113 (15)−0.0025 (13)0.0042 (15)
C40.0418 (15)0.0547 (18)0.073 (2)−0.0087 (14)−0.0095 (14)0.0147 (16)
C50.0564 (19)0.081 (3)0.073 (2)−0.0213 (18)0.0103 (16)0.025 (2)
C60.0558 (17)0.073 (2)0.0469 (16)−0.0075 (16)0.0102 (13)0.0139 (15)
C70.0332 (12)0.0350 (13)0.0388 (13)−0.0021 (10)0.0010 (10)−0.0040 (10)
C80.0348 (12)0.0436 (14)0.0419 (13)0.0021 (11)−0.0027 (10)−0.0035 (12)
O40.180 (3)0.131 (3)0.0514 (14)−0.070 (2)0.0235 (17)−0.0267 (17)
Geometric parameters (Å, º) top
Cl1—C41.739 (3)C3—C41.367 (4)
S1—O21.426 (2)C3—H30.9300
S1—O11.426 (2)C4—C51.380 (5)
S1—N11.644 (2)C5—C61.371 (5)
S1—C11.756 (3)C5—H50.9300
O3—C71.214 (3)C6—H60.9300
N1—C71.382 (3)C7—C81.503 (3)
N1—H1N0.837 (19)C8—C8i1.506 (5)
C1—C61.381 (4)C8—H810.9700
C1—C21.387 (4)C8—H820.9700
C2—C31.379 (4)O4—H410.8663
C2—H20.9300O4—H420.8435
O2—S1—O1119.62 (13)C3—C4—Cl1118.5 (3)
O2—S1—N1108.89 (12)C5—C4—Cl1119.9 (2)
O1—S1—N1104.31 (12)C6—C5—C4119.4 (3)
O2—S1—C1108.73 (12)C6—C5—H5120.3
O1—S1—C1108.76 (13)C4—C5—H5120.3
N1—S1—C1105.65 (12)C5—C6—C1119.7 (3)
C7—N1—S1125.20 (18)C5—C6—H6120.2
C7—N1—H1N119 (2)C1—C6—H6120.2
S1—N1—H1N114 (2)O3—C7—N1122.2 (2)
C6—C1—C2120.6 (3)O3—C7—C8124.3 (2)
C6—C1—S1119.6 (2)N1—C7—C8113.5 (2)
C2—C1—S1119.8 (2)C7—C8—C8i113.0 (3)
C3—C2—C1119.5 (3)C7—C8—H81109.0
C3—C2—H2120.2C8i—C8—H81109.0
C1—C2—H2120.2C7—C8—H82109.0
C4—C3—C2119.3 (3)C8i—C8—H82109.0
C4—C3—H3120.4H81—C8—H82107.8
C2—C3—H3120.4H41—O4—H4287.6
C3—C4—C5121.6 (3)
O2—S1—N1—C746.9 (3)C2—C3—C4—C5−0.3 (5)
O1—S1—N1—C7175.7 (2)C2—C3—C4—Cl1178.8 (3)
C1—S1—N1—C7−69.7 (2)C3—C4—C5—C60.5 (6)
O2—S1—C1—C6155.6 (2)Cl1—C4—C5—C6−178.6 (3)
O1—S1—C1—C623.9 (3)C4—C5—C6—C10.2 (6)
N1—S1—C1—C6−87.6 (3)C2—C1—C6—C5−1.0 (5)
O2—S1—C1—C2−25.8 (3)S1—C1—C6—C5177.5 (3)
O1—S1—C1—C2−157.6 (2)S1—N1—C7—O3−3.5 (4)
N1—S1—C1—C290.9 (2)S1—N1—C7—C8178.49 (19)
C6—C1—C2—C31.1 (5)O3—C7—C8—C8i9.9 (4)
S1—C1—C2—C3−177.4 (2)N1—C7—C8—C8i−172.1 (3)
C1—C2—C3—C4−0.5 (5)
Symmetry code: (i) −x, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O4ii0.84 (2)1.90 (2)2.735 (3)178 (3)
O4—H41···O30.872.273.137 (4)177
O4—H42···O2iii0.842.232.941 (3)142
O4—H42···O3iii0.842.583.262 (4)139
Symmetry codes: (ii) x, −y+1, z−1/2; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC16H14Cl2N2O6S2·2H2O
Mr501.34
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)33.349 (2), 4.9737 (4), 13.171 (1)
β (°) 90.660 (7)
V (Å3)2184.5 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.53
Crystal size (mm)0.48 × 0.40 × 0.12
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.784, 0.939
No. of measured, independent and
observed [I > 2σ(I)] reflections		3837, 2233, 1906
Rint0.012
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.120, 1.06
No. of reflections2233
No. of parameters139
No. of restraints7
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.55, −0.49

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···O4i0.837 (19)1.898 (19)2.735 (3)178 (3)
O4—H41···O30.872.273.137 (4)177.3
O4—H42···O2ii0.842.232.941 (3)142.4
O4—H42···O3ii0.842.583.262 (4)139.3
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, y+1, z.
 

Acknowledgements

HP thanks the Department of Science and Technology, Government of India, New Delhi, for a research fellowship under its INSPIRE Program. 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

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2063
https://doi.org/10.1107/S1600536812024725
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