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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 12| December 2010| Page o3162
https://doi.org/10.1107/S1600536810045538

4-Carbamoylpiperidinium acetate monohydrate

Graham Smitha* and Urs D. Wermutha

aFaculty of Science and Technology, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
*Correspondence e-mail: g.smith@qut.edu.au

(Received 4 November 2010; accepted 6 November 2010; online 13 November 2010)

In the structure of the title compound, C6H13N2O+·C2H3O2−·H2O, the amide H atoms of the cations form centrosymmetric cyclic hydrogen-bonding associations incorporating two water mol­ecules [graph set R42(8)], which are conjoint with cyclic water-bridged amide–amide associations [R44(12)] and larger R44(20) associations involving the water mol­ecule and the acetate anions, which bridge through the piperidinium H-bond donors, giving an overall three-dimensional framework structure.

Related literature

For structural data on isonipecotamide salts, see: Smith et al. (2010[Smith, G., Wermuth, U. D. & Young, D. J. (2010). Acta Cryst. E66, o3160-o3161.]); Smith & Wermuth (2010a[Smith, G. & Wermuth, U. D. (2010a). Acta Cryst. C66. Submitted. [FG3206]],b[Smith, G. & Wermuth, U. D. (2010b). Acta Cryst. C66. Accepted. [SU3056]]). For graph-set motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data

  • C6H13N2O+·C2H3O2−·H2O

  • Mr = 206.24

  • Triclinic, [P \overline 1]

  • a = 5.8219 (2) Å

  • b = 7.7675 (3) Å

  • c = 12.4022 (5) Å

  • α = 81.088 (4)°

  • β = 78.763 (4)°

  • γ = 76.202 (4)°

  • V = 530.75 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 200 K

  • 0.40 × 0.35 × 0.15 mm
Data collection

  • Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.962, Tmax = 0.980

  • 6385 measured reflections

  • 2087 independent reflections

  • 1602 reflections with I > 2σ(I)

  • Rint = 0.021
Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.105

  • S = 0.93

  • 2087 reflections

  • 151 parameters

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

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1A—H11A⋯O12i 0.940 (17) 1.793 (17) 2.7311 (16) 175.8 (17)
N1A—H12A⋯O11ii 0.949 (18) 1.824 (18) 2.7666 (16) 171.8 (14)
N41A—H41A⋯O1W 0.919 (18) 1.984 (18) 2.8939 (17) 170.2 (15)
N41A—H42A⋯O1Wiii 0.899 (17) 2.188 (16) 2.9491 (16) 142.1 (15)
O1W—H11W⋯O11 0.92 (2) 1.87 (2) 2.7871 (15) 172 (2)
O1W—H12W⋯O41Aiv 0.84 (2) 1.90 (2) 2.7370 (15) 177 (2)
Symmetry codes: (i) x, y+1, z; (ii) x-1, y+1, z; (iii) -x+2, -y, -z+1; (iv) x+1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045538/nk2071sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045538/nk2071Isup2.hkl

checkCIF report


Comment top

The amide 4-carbamoylpiperidine (isonipecotamide, INIPA) has proved to be a particularly useful synthon for the construction of crystalline salts with a range of aromatic carboxylic acids, enabling their structure determination (Smith & Wermuth, 2010a, 2010b). The structure of the 2:1 INIPA salt of biphenyl-4,4'-disulfonic acid has also been reported (Smith et al., 2010), and all reported compounds, prepared in aqueous ethanolic solution, have been anhydrous. No structures with aliphatic acids have previously been reported. However, our reaction of isonipecotamide with acetic acid in aqueous methanolic solution gave the title compound, the hydrate C6H13N2O+ C2H3O2-. H2O, (I) and the structure is reported here.

With (I) (Fig. 1) the amide H atoms of the cations form centrosymetric cyclic hydrogen-bonding associations which incorporate two water molecules [graph set R24(8) (Etter et al., 1990)], These are conjoint with cyclic water-bridged amide–amide associations [R44(12)] and larger R44(20) associations also involving the water molecule and the acetate anions (Table 1). These acetate groups bridge the cations through the piperidinium H donor atoms, giving an overall three-dimensional framework structure (Fig. 2).

Related literature top

For structural data on isonipecotamide salts, see: Smith et al. (2010); Smith & Wermuth (2010a,b). For graph-set motifs, see: Etter et al. (1990).

Experimental top

The title compound was synthesized by heating together under reflux for 10 minutes, 1 mmol quantities of 4-carbamoylpiperidine (isonipecotamide) and acetic acid in 50 ml of 80% methanol–water. After concentration to ca 30 ml, partial room temperature evaporation of the hot-filtered solution gave colourless plates of (I) (m.p. 409 K) from which a specimen was cleaved for the X-ray analysis.

Refinement top

Hydrogen atoms involved in hydrogen-bonding interactions were located by difference methods and their positional and isotropic displacement parameters were refined. The N–H bond distance range is 0.899 (17)–0.949 (18) Å and the water O–H distances are 0.82 (2) and 0.92 (2) Å. Other H-atoms were included in the refinement at calculated positions [C–H = 0.96–0.97 Å and with Uiso(H) = 1.2Ueq(C), using a riding-model approximation.

Structure description top

The amide 4-carbamoylpiperidine (isonipecotamide, INIPA) has proved to be a particularly useful synthon for the construction of crystalline salts with a range of aromatic carboxylic acids, enabling their structure determination (Smith & Wermuth, 2010a, 2010b). The structure of the 2:1 INIPA salt of biphenyl-4,4'-disulfonic acid has also been reported (Smith et al., 2010), and all reported compounds, prepared in aqueous ethanolic solution, have been anhydrous. No structures with aliphatic acids have previously been reported. However, our reaction of isonipecotamide with acetic acid in aqueous methanolic solution gave the title compound, the hydrate C6H13N2O+ C2H3O2-. H2O, (I) and the structure is reported here.

With (I) (Fig. 1) the amide H atoms of the cations form centrosymetric cyclic hydrogen-bonding associations which incorporate two water molecules [graph set R24(8) (Etter et al., 1990)], These are conjoint with cyclic water-bridged amide–amide associations [R44(12)] and larger R44(20) associations also involving the water molecule and the acetate anions (Table 1). These acetate groups bridge the cations through the piperidinium H donor atoms, giving an overall three-dimensional framework structure (Fig. 2).

For structural data on isonipecotamide salts, see: Smith et al. (2010); Smith & Wermuth (2010a,b). For graph-set motifs, see: Etter et al. (1990).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular configuration and atom naming scheme for the three INIPA cation the acetate anion and the water molecule of solvation in (I). Inter-species hydrogen bonds are shown as dashed lines and displacement ellipsoids are drawn at the 40% probability level.
[Figure 2] Fig. 2. The three-dimensional hydrogen-bonded framework structure of (I) viewed down the approximate b cell direction showing the cyclic R24(8), R44(12) and R44(20) hydrogen-bonding interactions in (I). Non-associative H atoms are omitted. For symmetry codes, see Table 1.
4-Carbamoylpiperidinium acetate monohydrate top
Crystal data top
C6H13N2O+·C2H3O2−·H2OZ = 2
Mr = 206.24F(000) = 224
Triclinic, P1Dx = 1.291 Mg m−3
Hall symbol: -P 1Melting point: 409 K
a = 5.8219 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.7675 (3) ÅCell parameters from 3330 reflections
c = 12.4022 (5) Åθ = 3.4–28.8°
α = 81.088 (4)°µ = 0.10 mm−1
β = 78.763 (4)°T = 200 K
γ = 76.202 (4)°Plate, colourless
V = 530.75 (4) Å30.40 × 0.35 × 0.15 mm
Data collection top
Oxford Diffraction Gemini-S Ultra CCD-detector
diffractometer		2087 independent reflections
Radiation source: Enhance (Mo) X-ray source1602 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 16.977 pixels mm-1θmax = 26.0°, θmin = 3.4°
ω scansh = −7→7
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		k = −9→9
Tmin = 0.962, Tmax = 0.980l = −15→15
6385 measured reflections
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 0.93 w = 1/[σ2(Fo2) + (0.0733P)2 + 0.0214P]
where P = (Fo2 + 2Fc2)/3
2087 reflections(Δ/σ)max < 0.001
151 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C6H13N2O+·C2H3O2−·H2Oγ = 76.202 (4)°
Mr = 206.24V = 530.75 (4) Å3
Triclinic, P1Z = 2
a = 5.8219 (2) ÅMo Kα radiation
b = 7.7675 (3) ŵ = 0.10 mm−1
c = 12.4022 (5) ÅT = 200 K
α = 81.088 (4)°0.40 × 0.35 × 0.15 mm
β = 78.763 (4)°
Data collection top
Oxford Diffraction Gemini-S Ultra CCD-detector
diffractometer		2087 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		1602 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.980Rint = 0.021
6385 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 0.93Δρmax = 0.20 e Å−3
2087 reflectionsΔρmin = −0.19 e Å−3
151 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O41A0.48609 (16)0.38864 (13)0.35243 (9)0.0344 (3)
N1A0.9204 (2)0.82745 (15)0.19803 (10)0.0274 (4)
N41A0.7954 (2)0.21185 (16)0.42814 (10)0.0297 (4)
C2A0.9917 (3)0.67001 (19)0.13552 (11)0.0290 (4)
C3A0.8415 (2)0.53343 (18)0.18703 (11)0.0264 (4)
C4A0.8642 (2)0.47820 (17)0.30875 (11)0.0223 (4)
C5A0.8010 (3)0.64377 (18)0.37045 (11)0.0283 (4)
C6A0.9525 (3)0.77742 (19)0.31557 (12)0.0319 (5)
C41A0.6994 (2)0.35378 (17)0.36412 (11)0.0236 (4)
O111.43436 (17)−0.04485 (13)0.19784 (8)0.0320 (3)
O121.14721 (18)0.09626 (14)0.10165 (9)0.0395 (4)
C11.3462 (2)0.08082 (17)0.12972 (11)0.0246 (4)
C21.4884 (3)0.2219 (2)0.08190 (13)0.0375 (5)
O1W1.31002 (18)0.08400 (15)0.40367 (9)0.0314 (3)
H4A1.030300.416900.313800.0270*
H11A1.005 (3)0.917 (2)0.1664 (15)0.050 (5)*
H12A0.757 (3)0.882 (2)0.1956 (14)0.043 (5)*
H21A1.160000.616600.136100.0350*
H22A0.969500.707000.059200.0350*
H31A0.894200.429100.147200.0320*
H32A0.674800.583900.180700.0320*
H41A0.958 (3)0.178 (2)0.4274 (13)0.036 (4)*
H42A0.701 (3)0.138 (2)0.4646 (14)0.045 (5)*
H51A0.632700.699200.371600.0340*
H52A0.827100.608500.446400.0340*
H61A0.905200.883000.354200.0380*
H62A1.120100.725600.319400.0380*
H211.429400.286900.016900.0450*
H221.654500.166100.062700.0450*
H231.471800.302500.135700.0450*
H11W1.355 (4)0.031 (3)0.3388 (19)0.069 (7)*
H12W1.368 (4)0.175 (3)0.3891 (17)0.062 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O41A0.0236 (5)0.0304 (6)0.0475 (6)−0.0104 (4)−0.0061 (4)0.0086 (5)
N1A0.0228 (6)0.0200 (6)0.0383 (7)−0.0088 (5)−0.0057 (5)0.0076 (5)
N41A0.0279 (7)0.0236 (6)0.0349 (7)−0.0100 (5)−0.0026 (5)0.0083 (5)
C2A0.0309 (7)0.0300 (8)0.0250 (7)−0.0108 (6)−0.0021 (6)0.0039 (6)
C3A0.0310 (7)0.0259 (7)0.0235 (7)−0.0116 (6)−0.0025 (5)−0.0007 (6)
C4A0.0192 (6)0.0198 (6)0.0269 (7)−0.0060 (5)−0.0038 (5)0.0029 (5)
C5A0.0345 (8)0.0271 (7)0.0247 (7)−0.0124 (6)−0.0020 (6)−0.0016 (6)
C6A0.0391 (8)0.0270 (8)0.0336 (8)−0.0155 (6)−0.0057 (6)−0.0032 (6)
C41A0.0239 (7)0.0202 (7)0.0256 (7)−0.0065 (5)−0.0007 (5)−0.0008 (6)
O110.0274 (5)0.0289 (5)0.0362 (6)−0.0050 (4)−0.0060 (4)0.0061 (5)
O120.0333 (6)0.0339 (6)0.0535 (7)−0.0167 (5)−0.0175 (5)0.0165 (5)
C10.0250 (7)0.0227 (7)0.0257 (7)−0.0074 (5)−0.0012 (5)−0.0015 (6)
C20.0368 (8)0.0335 (8)0.0450 (9)−0.0182 (7)−0.0080 (7)0.0054 (7)
O1W0.0325 (6)0.0304 (6)0.0324 (6)−0.0149 (5)−0.0066 (4)0.0073 (5)
Geometric parameters (Å, º) top
O41A—C41A1.2386 (16)C4A—C41A1.5186 (18)
O11—C11.2667 (16)C5A—C6A1.518 (2)
O12—C11.2473 (17)C2A—H21A0.9700
O1W—H12W0.84 (2)C2A—H22A0.9700
O1W—H11W0.92 (2)C3A—H32A0.9700
N1A—C6A1.4856 (19)C3A—H31A0.9700
N1A—C2A1.4816 (18)C4A—H4A0.9800
N41A—C41A1.3289 (18)C5A—H51A0.9700
N1A—H12A0.949 (18)C5A—H52A0.9700
N1A—H11A0.940 (17)C6A—H62A0.9700
N41A—H41A0.919 (18)C6A—H61A0.9700
N41A—H42A0.899 (17)C1—C21.509 (2)
C2A—C3A1.521 (2)C2—H230.9600
C3A—C4A1.5266 (19)C2—H210.9600
C4A—C5A1.5311 (19)C2—H220.9600
H11W—O1W—H12W104 (2)C2A—C3A—H32A109.00
C2A—N1A—C6A111.60 (11)C4A—C3A—H32A109.00
H11A—N1A—H12A104.9 (14)H31A—C3A—H32A108.00
C6A—N1A—H11A109.2 (11)C4A—C3A—H31A109.00
C2A—N1A—H11A112.5 (10)C5A—C4A—H4A109.00
C2A—N1A—H12A109.7 (10)C41A—C4A—H4A109.00
C6A—N1A—H12A108.8 (10)C3A—C4A—H4A109.00
C41A—N41A—H42A118.4 (11)C4A—C5A—H51A109.00
C41A—N41A—H41A121.8 (10)C6A—C5A—H51A109.00
H41A—N41A—H42A119.1 (15)C6A—C5A—H52A109.00
N1A—C2A—C3A110.23 (12)C4A—C5A—H52A109.00
C2A—C3A—C4A110.91 (11)H51A—C5A—H52A108.00
C3A—C4A—C41A111.67 (10)N1A—C6A—H62A110.00
C5A—C4A—C41A108.66 (11)C5A—C6A—H61A110.00
C3A—C4A—C5A109.87 (11)C5A—C6A—H62A110.00
C4A—C5A—C6A111.11 (12)H61A—C6A—H62A108.00
N1A—C6A—C5A109.84 (13)N1A—C6A—H61A110.00
O41A—C41A—C4A120.90 (12)O11—C1—O12123.79 (12)
O41A—C41A—N41A122.94 (12)O11—C1—C2117.89 (12)
N41A—C41A—C4A116.11 (11)O12—C1—C2118.31 (12)
N1A—C2A—H21A110.00C1—C2—H22109.00
C3A—C2A—H21A110.00C1—C2—H23109.00
C3A—C2A—H22A110.00C1—C2—H21109.00
H21A—C2A—H22A108.00H21—C2—H23109.00
N1A—C2A—H22A110.00H22—C2—H23109.00
C2A—C3A—H31A109.00H21—C2—H22109.00
C6A—N1A—C2A—C3A59.57 (16)C41A—C4A—C5A—C6A−177.38 (12)
C2A—N1A—C6A—C5A−59.60 (16)C3A—C4A—C41A—O41A−47.52 (17)
N1A—C2A—C3A—C4A−56.87 (15)C3A—C4A—C41A—N41A135.05 (12)
C2A—C3A—C4A—C5A54.57 (15)C5A—C4A—C41A—O41A73.82 (16)
C2A—C3A—C4A—C41A175.21 (11)C5A—C4A—C41A—N41A−103.61 (14)
C3A—C4A—C5A—C6A−54.94 (16)C4A—C5A—C6A—N1A57.10 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H11A···O12i0.940 (17)1.793 (17)2.7311 (16)175.8 (17)
N1A—H12A···O11ii0.949 (18)1.824 (18)2.7666 (16)171.8 (14)
N41A—H41A···O1W0.919 (18)1.984 (18)2.8939 (17)170.2 (15)
N41A—H42A···O1Wiii0.899 (17)2.188 (16)2.9491 (16)142.1 (15)
O1W—H11W···O110.92 (2)1.87 (2)2.7871 (15)172 (2)
O1W—H12W···O41Aiv0.84 (2)1.90 (2)2.7370 (15)177 (2)
C2A—H22A···O12v0.972.423.3428 (18)158
Symmetry codes: (i) x, y+1, z; (ii) x−1, y+1, z; (iii) −x+2, −y, −z+1; (iv) x+1, y, z; (v) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC6H13N2O+·C2H3O2−·H2O
Mr206.24
Crystal system, space groupTriclinic, P1
Temperature (K)200
a, b, c (Å)5.8219 (2), 7.7675 (3), 12.4022 (5)
α, β, γ (°)81.088 (4), 78.763 (4), 76.202 (4)
V (Å3)530.75 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.40 × 0.35 × 0.15
Data collection
DiffractometerOxford Diffraction Gemini-S Ultra CCD-detector
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.962, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections		6385, 2087, 1602
Rint0.021
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.105, 0.93
No. of reflections2087
No. of parameters151
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.20, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H11A···O12i0.940 (17)1.793 (17)2.7311 (16)175.8 (17)
N1A—H12A···O11ii0.949 (18)1.824 (18)2.7666 (16)171.8 (14)
N41A—H41A···O1W0.919 (18)1.984 (18)2.8939 (17)170.2 (15)
N41A—H42A···O1Wiii0.899 (17)2.188 (16)2.9491 (16)142.1 (15)
O1W—H11W···O110.92 (2)1.87 (2)2.7871 (15)172 (2)
O1W—H12W···O41Aiv0.84 (2)1.90 (2)2.7370 (15)177 (2)
Symmetry codes: (i) x, y+1, z; (ii) x−1, y+1, z; (iii) −x+2, −y, −z+1; (iv) x+1, y, z.
 

Acknowledgements

The authors acknowledge financial support from the Australian Research Council, the Faculty of Science and Technology, Queensland University of Technology and the School of Biomolecular and Physical Sciences, Griffith University.

References

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3162
https://doi.org/10.1107/S1600536810045538
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