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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 8| August 2011| Page o2166
doi:10.1107/S1600536811029242

3-Amino-N′-(2-oxoindolin-3-yl­­idene)benzohydrazide

Rifat Ara Jamal,a* Uzma Ashiq,a Sammer Yousufb and Qurrat ul Aina

aDepartment of Chemistry, University of Karachi, Karachi 75270, Pakistan, and bH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
*Correspondence e-mail: rifat_jamal@yahoo.com

(Received 15 July 2011; accepted 19 July 2011; online 30 July 2011)

The title compound, C15H12N4O2, contains two substituted benzohydrazide and indole rings linked via a C=N double bond. The dihedral angle between the benzene ring and the indole ring system is 11.38 (10)°. The mol­ecular structure is stabilized by an intra­molecular N—H⋯O hydrogen bond, forming a six-membered ring. The crystal structure is consolidated by inter­molecular N—H⋯O and C—H⋯O inter­actions, which result in sheets.

Related literature

For the biological activity of related compounds, see: Ashiq et al. (2008[Ashiq, U., Ara, R., Mahroof-Tahir, M., Maqsood, Z. T., Khan, K. M., Khan, S. N., Siddiqui, H. & Choudhary, M. I. (2008). Chem. Biodivers. 5, 82-92.]); Maqsood et al. (2006[Maqsood, Z. T., Khan, K. M., Ashiq, U., Ara, R., Chohan, Z. H., Mahroof-Tahir, M. & Supuran, C. T. (2006). J. Enz. Inhib. Med. Chem. 21, 37-42.]); Sarangapani & Reddy (1994[Sarangapani, M. & Reddy, V. M. (1994). Indian J. Pharm. Sci. 56, 174-177.]). For related structures, see: Bai et al. (2006[Bai, Z.-C., Li, H., Liu, Y. & Jing, Z.-L. (2006). Acta Cryst. E62, o2295-o2296.]); Yang & Pan (2004[Yang, J.-G. & Pan, F.-Y. (2004). Acta Cryst. E60, o2009-o2010.]).

[Scheme 1]

Experimental

Crystal data

  • C15H12N4O2

  • Mr = 280.29

  • Monoclinic, P 21 /c

  • a = 8.8036 (8) Å

  • b = 8.9040 (7) Å

  • c = 17.0732 (14) Å

  • β = 92.335 (2)°

  • V = 1337.21 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 273 K

  • 0.17 × 0.17 × 0.12 mm
Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.984, Tmax = 0.989

  • 7637 measured reflections

  • 2491 independent reflections

  • 1551 reflections with I > 2σ(I)

  • Rint = 0.047
Refinement

  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.122

  • S = 0.99

  • 2491 reflections

  • 198 parameters

  • 1 restraint

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

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O2i 0.86 2.02 2.785 (2) 148
N3—H3A⋯O1 0.86 2.09 2.757 (2) 133
N4—H4C⋯N2ii 0.86 (2) 2.61 (2) 3.423 (3) 158 (2)
C12—H12A⋯O1iii 0.93 2.59 3.424 (3) 149
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+2, -y+1, -z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811029242/pv2431sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029242/pv2431Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029242/pv2431Isup3.cml

checkCIF report


Comment top

Compounds containing hydrazide moiety have been revealed to exhibit a wide variety of interesting biological properties (Ashiq et al. 2008; Maqsood et al. 2006). In a quest to expand and further explore the biological significance of hydrazides, we have undertken a task to synthesize new Schiff bases of isatin with hydrazides. Isatins are very important compounds due to their antifungal properties (Sarangapani & Reddy, 1994). In this article we report the synthesis and crystal structure of the title compound.

The title molecule (Fig. 1) consists of substituted benzohydrazide and indole rings linked by C═N bond. The dihedral angle between the two substituted benzene (C10—C15) and indole ring (N1/C1—C8) is 11.38 (10)°. The bond lengths and angles are in normal range as in other structurally related compounds (Bai et al. 2006; Yang & Pan, 2004). The geometry of the molecule is stabilized by N3—H3A···O1 intramolecular hydrogen bond resulting in a six membered ring. In the crystal structure, the molecules are linked to form two-dimensional sheets via N1—H1A···O2, N4—H4C···N2 and C12—H12A···O1 intermolecular hydrogen bonds (Tab. 1 & Fig. 2).

Related literature top

For the biological activity of related compounds, see: Ashiq et al. (2008); Maqsood et al. (2006); Sarangapani & Reddy (1994). For related structures, see: Bai et al. (2006); Yang & Pan (2004).

Experimental top

To a solution of 2,3-indolinedione (10 mmol, 1.47 g) in 15 ml of ethanol with a few drops of glacial acetic acid and 3-aminobenzohydrazide (10 mmol, 1.51 g) in 15 ml ethanol were added. The mixture was refluxed for 2 h and a solid was obtained upon removal of the solvent by rotary evaporation. The resulting solid was washed with ethanol to afford the title compound (yield 75%). The crystals of the title compound suitable for XRD analysis were grown from a mixture of ethanol and methanol (1:1) by slow evaporation at room temperature.

Refinement top

H atoms on the C atoms and N1 and N3 were positioned geomatrically with C–H = 0.93 and N–H = 0.86 Å and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C/N). The H atoms on N4 were located from a difference Fourier map and refined isotropically.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule with displacement ellipsoids drawn at 50% probability level. The dashed lines indicate intramolecular hydrogen bond.
[Figure 2] Fig. 2. The crystal packing of the title compound.Hydrogen atoms not involved in hydrogen bonding have been excluded for clarity.
3-Amino-N'-(2-oxoindolin-3-ylidene)benzohydrazide top
Crystal data top
C15H12N4O2F(000) = 584
Mr = 280.29Dx = 1.392 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1161 reflections
a = 8.8036 (8) Åθ = 2.4–27.8°
b = 8.9040 (7) ŵ = 0.10 mm−1
c = 17.0732 (14) ÅT = 273 K
β = 92.335 (2)°Block, colorless
V = 1337.21 (19) Å30.17 × 0.17 × 0.12 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2491 independent reflections
Radiation source: fine-focus sealed tube1551 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −10→10
Tmin = 0.984, Tmax = 0.989k = −10→10
7637 measured reflectionsl = −20→20
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0584P)2]
where P = (Fo2 + 2Fc2)/3
2491 reflections(Δ/σ)max < 0.001
198 parametersΔρmax = 0.18 e Å−3
1 restraintΔρmin = −0.17 e Å−3
Crystal data top
C15H12N4O2V = 1337.21 (19) Å3
Mr = 280.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.8036 (8) ŵ = 0.10 mm−1
b = 8.9040 (7) ÅT = 273 K
c = 17.0732 (14) Å0.17 × 0.17 × 0.12 mm
β = 92.335 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2491 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1551 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.989Rint = 0.047
7637 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0521 restraint
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.18 e Å−3
2491 reflectionsΔρmin = −0.17 e Å−3
198 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
O10.66942 (18)0.35101 (18)−0.07613 (8)0.0531 (5)
O20.53184 (19)0.37905 (18)0.20442 (8)0.0568 (5)
N10.5172 (2)0.1671 (2)−0.13475 (10)0.0470 (5)
H1A0.55780.1631−0.17970.056*
N20.4730 (2)0.27880 (19)0.06115 (9)0.0407 (5)
N30.5848 (2)0.38136 (19)0.07676 (9)0.0415 (5)
H3A0.63770.41690.03980.050*
N40.8354 (3)0.8078 (3)0.32398 (15)0.0676 (7)
C10.2412 (3)0.0351 (3)−0.00233 (13)0.0488 (6)
H1B0.21750.05450.04930.059*
C20.1601 (3)−0.0703 (3)−0.04635 (15)0.0557 (7)
H2A0.0815−0.1229−0.02410.067*
C30.1950 (3)−0.0980 (3)−0.12350 (14)0.0569 (7)
H3B0.1379−0.1682−0.15240.068*
C40.3119 (3)−0.0245 (3)−0.15845 (13)0.0523 (7)
H4A0.3354−0.0442−0.21010.063*
C50.3923 (2)0.0790 (2)−0.11405 (12)0.0417 (6)
C60.5659 (3)0.2585 (3)−0.07583 (12)0.0409 (6)
C70.4654 (2)0.2238 (2)−0.00862 (11)0.0374 (5)
C80.3583 (2)0.1110 (2)−0.03664 (12)0.0391 (5)
C90.6110 (2)0.4264 (2)0.15255 (12)0.0406 (6)
C100.7362 (2)0.5353 (2)0.16743 (12)0.0400 (6)
C110.8540 (3)0.5576 (3)0.11661 (13)0.0518 (6)
H11A0.85820.50270.07040.062*
C120.9645 (3)0.6629 (3)0.13619 (15)0.0606 (7)
H12A1.04420.67780.10300.073*
C130.9587 (3)0.7457 (3)0.20365 (16)0.0586 (7)
H13A1.03420.81610.21540.070*
C140.8416 (3)0.7259 (3)0.25467 (14)0.0490 (6)
C150.7329 (3)0.6181 (2)0.23602 (13)0.0440 (6)
H15A0.65550.60090.27040.053*
H4C0.7478 (19)0.819 (3)0.3435 (17)0.099 (12)*
H4B0.889 (4)0.894 (3)0.3239 (17)0.101 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0485 (10)0.0635 (11)0.0480 (9)−0.0019 (9)0.0114 (8)0.0040 (8)
O20.0650 (11)0.0715 (12)0.0346 (8)−0.0188 (9)0.0111 (8)−0.0022 (8)
N10.0485 (12)0.0630 (12)0.0299 (9)0.0067 (11)0.0055 (9)0.0003 (9)
N20.0402 (11)0.0452 (11)0.0366 (10)0.0030 (9)0.0024 (9)0.0015 (8)
N30.0439 (11)0.0476 (11)0.0334 (10)−0.0005 (10)0.0080 (9)0.0016 (8)
N40.0598 (18)0.0655 (16)0.0765 (16)−0.0067 (14)−0.0089 (14)−0.0142 (14)
C10.0431 (14)0.0557 (15)0.0473 (13)0.0064 (13)0.0012 (12)0.0011 (12)
C20.0413 (15)0.0549 (16)0.0704 (17)0.0005 (13)−0.0028 (13)0.0059 (14)
C30.0515 (16)0.0529 (15)0.0644 (17)0.0076 (13)−0.0192 (14)−0.0053 (13)
C40.0566 (17)0.0566 (15)0.0429 (13)0.0126 (14)−0.0088 (13)−0.0042 (12)
C50.0392 (13)0.0476 (13)0.0377 (12)0.0125 (12)−0.0042 (11)0.0000 (11)
C60.0366 (14)0.0488 (14)0.0372 (12)0.0113 (12)0.0017 (11)0.0042 (11)
C70.0364 (13)0.0432 (13)0.0326 (11)0.0115 (11)0.0013 (10)0.0028 (10)
C80.0354 (12)0.0437 (13)0.0379 (11)0.0089 (11)−0.0004 (10)0.0025 (10)
C90.0436 (14)0.0440 (13)0.0345 (12)0.0075 (11)0.0040 (11)0.0023 (10)
C100.0361 (13)0.0412 (13)0.0426 (12)0.0055 (11)0.0021 (10)0.0070 (11)
C110.0452 (15)0.0603 (16)0.0504 (13)0.0042 (13)0.0079 (12)0.0053 (12)
C120.0403 (15)0.0737 (18)0.0685 (17)−0.0012 (14)0.0084 (14)0.0180 (15)
C130.0447 (16)0.0558 (16)0.0743 (17)−0.0074 (13)−0.0084 (14)0.0100 (14)
C140.0428 (15)0.0479 (14)0.0557 (14)0.0047 (12)−0.0055 (13)0.0030 (12)
C150.0377 (13)0.0472 (14)0.0470 (13)0.0014 (11)−0.0012 (11)0.0047 (11)
Geometric parameters (Å, º) top
O1—C61.228 (2)C3—H3B0.9300
O2—C91.224 (2)C4—C51.372 (3)
N1—C61.351 (3)C4—H4A0.9300
N1—C51.407 (3)C5—C81.396 (3)
N1—H1A0.8600C6—C71.509 (3)
N2—C71.287 (2)C7—C81.446 (3)
N2—N31.361 (2)C9—C101.482 (3)
N3—C91.365 (2)C10—C151.385 (3)
N3—H3A0.8600C10—C111.393 (3)
N4—C141.393 (3)C11—C121.382 (3)
N4—H4C0.858 (10)C11—H11A0.9300
N4—H4B0.90 (3)C12—C131.370 (3)
C1—C21.382 (3)C12—H12A0.9300
C1—C81.383 (3)C13—C141.388 (3)
C1—H1B0.9300C13—H13A0.9300
C2—C31.387 (3)C14—C151.383 (3)
C2—H2A0.9300C15—H15A0.9300
C3—C41.376 (3)
C6—N1—C5112.13 (18)N2—C7—C8125.39 (19)
C6—N1—H1A123.9N2—C7—C6128.0 (2)
C5—N1—H1A123.9C8—C7—C6106.59 (17)
C7—N2—N3116.52 (17)C1—C8—C5119.6 (2)
N2—N3—C9118.39 (17)C1—C8—C7133.39 (19)
N2—N3—H3A120.8C5—C8—C7107.01 (18)
C9—N3—H3A120.8O2—C9—N3120.4 (2)
C14—N4—H4C117 (2)O2—C9—C10122.86 (19)
C14—N4—H4B113.9 (19)N3—C9—C10116.76 (18)
H4C—N4—H4B113 (3)C15—C10—C11119.5 (2)
C2—C1—C8118.6 (2)C15—C10—C9116.88 (19)
C2—C1—H1B120.7C11—C10—C9123.6 (2)
C8—C1—H1B120.7C12—C11—C10118.7 (2)
C1—C2—C3120.5 (2)C12—C11—H11A120.6
C1—C2—H2A119.7C10—C11—H11A120.6
C3—C2—H2A119.7C13—C12—C11121.2 (2)
C4—C3—C2121.7 (2)C13—C12—H12A119.4
C4—C3—H3B119.2C11—C12—H12A119.4
C2—C3—H3B119.2C12—C13—C14120.9 (2)
C5—C4—C3117.3 (2)C12—C13—H13A119.6
C5—C4—H4A121.4C14—C13—H13A119.6
C3—C4—H4A121.4C15—C14—C13117.9 (2)
C4—C5—C8122.3 (2)C15—C14—N4120.5 (2)
C4—C5—N1128.8 (2)C13—C14—N4121.5 (2)
C8—C5—N1108.91 (19)C14—C15—C10121.7 (2)
O1—C6—N1127.9 (2)C14—C15—H15A119.1
O1—C6—C7126.8 (2)C10—C15—H15A119.1
N1—C6—C7105.3 (2)
C7—N2—N3—C9−170.74 (18)N1—C5—C8—C70.4 (2)
C8—C1—C2—C3−0.5 (3)N2—C7—C8—C10.8 (4)
C1—C2—C3—C41.1 (4)C6—C7—C8—C1179.3 (2)
C2—C3—C4—C5−0.6 (3)N2—C7—C8—C5−177.82 (19)
C3—C4—C5—C8−0.4 (3)C6—C7—C8—C50.6 (2)
C3—C4—C5—N1178.9 (2)N2—N3—C9—O2−2.5 (3)
C6—N1—C5—C4179.2 (2)N2—N3—C9—C10178.53 (17)
C6—N1—C5—C8−1.4 (2)O2—C9—C10—C15−19.6 (3)
C5—N1—C6—O1−178.1 (2)N3—C9—C10—C15159.37 (19)
C5—N1—C6—C71.7 (2)O2—C9—C10—C11160.6 (2)
N3—N2—C7—C8178.30 (18)N3—C9—C10—C11−20.5 (3)
N3—N2—C7—C60.2 (3)C15—C10—C11—C12−0.2 (3)
O1—C6—C7—N2−3.2 (4)C9—C10—C11—C12179.6 (2)
N1—C6—C7—N2177.0 (2)C10—C11—C12—C13−0.7 (4)
O1—C6—C7—C8178.4 (2)C11—C12—C13—C140.2 (4)
N1—C6—C7—C8−1.4 (2)C12—C13—C14—C151.2 (4)
C2—C1—C8—C5−0.5 (3)C12—C13—C14—N4179.1 (2)
C2—C1—C8—C7−179.0 (2)C13—C14—C15—C10−2.2 (3)
C4—C5—C8—C11.0 (3)N4—C14—C15—C10179.9 (2)
N1—C5—C8—C1−178.47 (19)C11—C10—C15—C141.7 (3)
C4—C5—C8—C7179.85 (19)C9—C10—C15—C14−178.15 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.022.785 (2)148
N3—H3A···O10.862.092.757 (2)133
N4—H4C···N2ii0.86 (2)2.61 (2)3.423 (3)158 (2)
C12—H12A···O1iii0.932.593.424 (3)149
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC15H12N4O2
Mr280.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)8.8036 (8), 8.9040 (7), 17.0732 (14)
β (°) 92.335 (2)
V (Å3)1337.21 (19)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.17 × 0.17 × 0.12
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.984, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections		7637, 2491, 1551
Rint0.047
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.122, 0.99
No. of reflections2491
No. of parameters198
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.18, −0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.022.785 (2)148
N3—H3A···O10.862.092.757 (2)133
N4—H4C···N2ii0.86 (2)2.61 (2)3.423 (3)158 (2)
C12—H12A···O1iii0.932.593.424 (3)149
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+2, −y+1, −z.
 

Acknowledgements

The authors are thankful to the Higher Education Commission (HEC) Pakistan for financial support under the National Research Grants Program for Universities (grant No. 20–1862/R&D/10).

References

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ISSN: 2056-9890
Volume 67| Part 8| August 2011| Page o2166
doi:10.1107/S1600536811029242
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