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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 o3106
https://doi.org/10.1107/S160053681004448X

(E)-2,4-Di­chloro-6-{1-[(2-chloro­eth­yl)imino]­eth­yl}phenol

Yong-Sheng Xie,a* Wen-Liang Dong,b Li-Ping He,a Xin-Ling Zhangc and Bao-Xiang Zhaod

aCollege of Chemical and Environment Engineering, Chongqing Three Gorges University, Chongqing 404100, People's Republic of China, bShandong University of Traditional Chinese Medicine, Jinan 250355, People's Republic of China, cEditorial Department of College Journal, Chongqing Three Gorges University, Chongqing 404100, People's Republic of China, and dSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
*Correspondence e-mail: yshxl@yahoo.com.cn

(Received 10 October 2010; accepted 31 October 2010; online 10 November 2010)

The title Schiff base compound, C10H10Cl3NO, was prepared by the condensation of 1-(3,5-dichloro-2-hy­droxy­phen­yl)ethanone with chloro­ethyl­amine. The imine adopts an E configuration with respect to the C=N bond. The H atom of the phenolic OH group is disordered over two positions with site occupation factors of 0.52 (7) and 0.48 (7), respectively, and the major occupancy component is involved in an intramolecular N—H⋯O hydrogen bond. The compound therefore exists in an iminium–phenolate as well as in the imino–phenol form. In the crystal, mol­ecules are connected by C—H⋯O and C—H⋯Cl hydrogen bonds and Cl⋯Cl inter­actions [3.7864 (9) Å] into a three-dimensional network. In addition, inter­molecular π–π stacking inter­actions [centroid–centroid distance = 4.4312 (9) Å] are observed.

Related literature

For a related structure, see: Wang et al. (2010[Wang, C.-H., Liu, Y.-C., Lin, C.-H. & Ko, B.-T. (2010). Acta Cryst. E66, o745.]). For applications of Schiff base ligands, see: Yin et al. (2004[Yin, H. D., Wang, Q. B. & Xue, S. C. (2004). J. Organomet. Chem. 689, 2480-2485.]); Böhme & Günther (2007[Böhme, U. & Günther, B. (2007). Inorg. Chem. Commun. 10, 482-484.]).

[Scheme 1]

Experimental

Crystal data

  • C10H10Cl3NO

  • Mr = 266.54

  • Monoclinic, P 21 /c

  • a = 14.5710 (2) Å

  • b = 10.2323 (2) Å

  • c = 7.7384 (1) Å

  • β = 94.376 (1)°

  • V = 1150.39 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.77 mm−1

  • T = 296 K

  • 0.38 × 0.19 × 0.07 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.762, Tmax = 0.951

  • 8253 measured reflections

  • 2625 independent reflections

  • 1940 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.091

  • S = 1.02

  • 2625 reflections

  • 146 parameters

  • 2 restraints

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

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1 0.88 (2) 1.68 (2) 2.479 (2) 150 (4)
C10—H10B⋯O1i 0.97 2.48 3.416 (2) 159
C10—H10A⋯Cl3ii 0.97 2.86 3.621 (2) 136
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681004448X/im2238sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004448X/im2238Isup2.hkl

checkCIF report


Comment top

Schiff-base ligands have attracted much attention over the years, e.g. as ligands in organotin(IV) compounds owing to their anti-tumour activities (Yin et al., 2004), and in silicon complexes applied to the field of photovoltaic applications, as coloring material and due to their antimicrobial activity. (Böhme & Günther, 2007). We report here the crystal structure of the title Schiff-base ligand (Fig. 1).

The molecular structure of the ligand is represented in Fig. 1. The bond lengths and angles are in eligible range. The C7—N1 and C9—N1 bond lengths of 1.290 (2), 1.460 (2) Å, respectively, conform to the value for a double and single bonds and they are comparable with the corresponding bond lengths in similar Schiff-base compounds (Wang et al., 2010). The hydrogen atom of the phenolic OH group is disordered over two positions with site occupation factors of 0.52 and 0.48, respectively. The compound therefore exists in an iminium-phenolate as well as in an imino-phenol form. The situation may be interpreted as the intramolecular protonation of the basic imine nitrogen by the acidic phenol group. In the crystal, molecules are connected by C—H···O, C—H···Cl (Table 1) and Cl···Cl interactions [Cl1···Cl2 distance = 3.7864 (9) Å for symmetry operation -x + 1, -y + 1, -z; Cl2···Cl3 distance = 3.7709 (7) Å for symmetry operation -x + 2, y - 1/2, -z + 1/2; Cl2···Cl3 distance = 3.7789 (8) Å for symmetry operation -x + 2, -y + 1, -z] into a network (Fig. 2). In addition, weak intermolecular π–π interactions serve to stabilize the extended structure [Cg···Cg distance = 4.4312 (9) Å for symmetry operation x, -y + 1/2, z - 1/2 and x, -y + 1/2, z + 1/2 (The Cg is the centroid of the phenyl ring)].

Related literature top

For a related structure, see: Wang et al. (2010). For applications of Schiff base ligands, see: Yin et al. (2004); Böhme & Günther (2007).

Experimental top

To a mixture of 1-(3,5-dichloro-2-hydroxy-phenyl)-ethanone (5.1 g, 25 mmol) and chloroethylamine hydrochloride (5.8 g, 50 mmol) in ethanol (150 ml) was added triethylamine (5.1 g, 50 mmol). The mixture was heated to reflux for 10 min. After being cooled to room temperature, the resulting precipitate was filtrated and washed with water to afford the product, E-2,4-dichloro-6-(1-(2-chloroethylimino)ethyl)phenol in 84% yield. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in ethyl acetate at room temperature for 7 d.

Refinement top

All H atoms at carbon were placed geometrically and refined using a riding model with C—H = 0.97 Å (for CH2 group), 0.96 Å (for CH3 group) and 0.93 Å (for aryl H atoms). The isotropic atomic displacement parameters of hydrogen atoms were set to 1.5 × Ueq (CH3) and 1.2 × Ueq (CH2, CarH) of the parent atoms. Positions of hydrogen atoms at N1 and O1 were taken from difference Fourier maps and were refined using PART instructions.

Structure description top

Schiff-base ligands have attracted much attention over the years, e.g. as ligands in organotin(IV) compounds owing to their anti-tumour activities (Yin et al., 2004), and in silicon complexes applied to the field of photovoltaic applications, as coloring material and due to their antimicrobial activity. (Böhme & Günther, 2007). We report here the crystal structure of the title Schiff-base ligand (Fig. 1).

The molecular structure of the ligand is represented in Fig. 1. The bond lengths and angles are in eligible range. The C7—N1 and C9—N1 bond lengths of 1.290 (2), 1.460 (2) Å, respectively, conform to the value for a double and single bonds and they are comparable with the corresponding bond lengths in similar Schiff-base compounds (Wang et al., 2010). The hydrogen atom of the phenolic OH group is disordered over two positions with site occupation factors of 0.52 and 0.48, respectively. The compound therefore exists in an iminium-phenolate as well as in an imino-phenol form. The situation may be interpreted as the intramolecular protonation of the basic imine nitrogen by the acidic phenol group. In the crystal, molecules are connected by C—H···O, C—H···Cl (Table 1) and Cl···Cl interactions [Cl1···Cl2 distance = 3.7864 (9) Å for symmetry operation -x + 1, -y + 1, -z; Cl2···Cl3 distance = 3.7709 (7) Å for symmetry operation -x + 2, y - 1/2, -z + 1/2; Cl2···Cl3 distance = 3.7789 (8) Å for symmetry operation -x + 2, -y + 1, -z] into a network (Fig. 2). In addition, weak intermolecular π–π interactions serve to stabilize the extended structure [Cg···Cg distance = 4.4312 (9) Å for symmetry operation x, -y + 1/2, z - 1/2 and x, -y + 1/2, z + 1/2 (The Cg is the centroid of the phenyl ring)].

For a related structure, see: Wang et al. (2010). For applications of Schiff base ligands, see: Yin et al. (2004); Böhme & Günther (2007).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Crystal packing of title compound viewed along the b axis. C—H···O and C—H···Cl hydrogen bonds are displayed as red and blue dashed lines, respectively. Cl···Cl interactions are shown as green dashed lines.
[Figure 3] Fig. 3. Crystal packing of title compound viewed along the c axis. The π–π interactions are shown as black dashed lines.
(E)-2,4-Dichloro-6-{1-[(2-chloroethyl)imino]ethyl}phenol top
Crystal data top
C10H10Cl3NOF(000) = 544
Mr = 266.54Dx = 1.539 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2504 reflections
a = 14.5710 (2) Åθ = 2.4–25.9°
b = 10.2323 (2) ŵ = 0.77 mm−1
c = 7.7384 (1) ÅT = 296 K
β = 94.376 (1)°Plate, orange
V = 1150.39 (3) Å30.38 × 0.19 × 0.07 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2625 independent reflections
Radiation source: fine-focus sealed tube1940 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −18→17
Tmin = 0.762, Tmax = 0.951k = −10→13
8253 measured reflectionsl = −8→10
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0452P)2 + 0.1559P]
where P = (Fo2 + 2Fc2)/3
2625 reflections(Δ/σ)max = 0.006
146 parametersΔρmax = 0.25 e Å−3
2 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C10H10Cl3NOV = 1150.39 (3) Å3
Mr = 266.54Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.5710 (2) ŵ = 0.77 mm−1
b = 10.2323 (2) ÅT = 296 K
c = 7.7384 (1) Å0.38 × 0.19 × 0.07 mm
β = 94.376 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2625 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		1940 reflections with I > 2σ(I)
Tmin = 0.762, Tmax = 0.951Rint = 0.023
8253 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0332 restraints
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.25 e Å−3
2625 reflectionsΔρmin = −0.21 e Å−3
146 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*/UeqOcc. (<1)
C10.57736 (13)0.15817 (19)−0.1505 (2)0.0498 (4)
C20.61146 (13)0.0340 (2)−0.1143 (2)0.0516 (5)
H20.5771−0.0395−0.14810.062*
C30.69659 (12)0.02119 (17)−0.0279 (2)0.0455 (4)
C40.75065 (12)0.12988 (16)0.0289 (2)0.0401 (4)
C50.71381 (12)0.25627 (16)−0.0117 (2)0.0388 (4)
C60.62665 (12)0.26726 (18)−0.1027 (2)0.0458 (4)
H60.60260.3495−0.13030.055*
C70.76729 (12)0.37256 (16)0.0405 (2)0.0403 (4)
C80.73432 (14)0.50736 (18)−0.0072 (3)0.0559 (5)
H8A0.66890.51220.00020.084*
H8B0.74870.5268−0.12350.084*
H8C0.76420.56960.07100.084*
C90.90715 (13)0.45820 (17)0.1910 (2)0.0491 (4)
H9A0.87490.51890.26110.059*
H9B0.92760.50570.09250.059*
C100.98893 (13)0.40380 (19)0.2962 (2)0.0509 (5)
H10A0.96820.35820.39610.061*
H10B1.02840.47520.33820.061*
Cl10.46922 (4)0.17442 (7)−0.26165 (8)0.0791 (2)
Cl20.74236 (4)−0.13318 (4)0.01161 (8)0.06643 (18)
Cl31.05345 (3)0.29415 (5)0.17400 (7)0.05817 (16)
N10.84464 (10)0.35378 (14)0.12961 (19)0.0418 (3)
H1N0.858 (3)0.271 (2)0.146 (5)0.049 (16)*0.52 (7)
H1O0.855 (3)0.183 (3)0.145 (6)0.07 (2)*0.48 (7)
O10.83069 (9)0.11256 (12)0.11379 (18)0.0494 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0381 (10)0.0583 (11)0.0523 (10)−0.0039 (9)−0.0005 (8)0.0049 (9)
C20.0472 (11)0.0491 (10)0.0583 (11)−0.0119 (9)0.0041 (9)−0.0039 (9)
C30.0451 (10)0.0370 (9)0.0551 (10)−0.0010 (8)0.0077 (8)−0.0016 (7)
C40.0392 (10)0.0368 (8)0.0450 (9)−0.0005 (7)0.0069 (7)−0.0006 (7)
C50.0387 (9)0.0364 (8)0.0417 (9)−0.0005 (7)0.0051 (7)0.0023 (7)
C60.0421 (10)0.0449 (10)0.0506 (10)0.0042 (8)0.0041 (8)0.0077 (8)
C70.0428 (10)0.0360 (8)0.0428 (9)0.0027 (7)0.0081 (7)0.0028 (7)
C80.0577 (12)0.0382 (9)0.0709 (12)0.0041 (9)−0.0014 (10)0.0076 (9)
C90.0515 (11)0.0348 (8)0.0610 (11)−0.0068 (8)0.0040 (9)−0.0030 (8)
C100.0561 (12)0.0511 (10)0.0450 (9)−0.0121 (9)0.0002 (8)−0.0071 (8)
Cl10.0484 (3)0.0859 (4)0.0987 (4)−0.0121 (3)−0.0218 (3)0.0179 (3)
Cl20.0629 (4)0.0339 (2)0.1020 (4)0.0003 (2)0.0030 (3)−0.0027 (2)
Cl30.0544 (3)0.0519 (3)0.0673 (3)0.0025 (2)−0.0016 (2)−0.0059 (2)
N10.0448 (9)0.0310 (7)0.0493 (8)−0.0020 (6)0.0019 (7)−0.0003 (6)
O10.0408 (7)0.0350 (7)0.0710 (8)0.0018 (6)−0.0055 (6)0.0007 (6)
Geometric parameters (Å, º) top
C1—C61.363 (3)C7—C81.498 (2)
C1—C21.385 (3)C8—H8A0.9600
C1—Cl11.7446 (19)C8—H8B0.9600
C2—C31.370 (2)C8—H8C0.9600
C2—H20.9300C9—N11.460 (2)
C3—C41.413 (2)C9—C101.498 (3)
C3—Cl21.7326 (18)C9—H9A0.9700
C4—O11.306 (2)C9—H9B0.9700
C4—C51.426 (2)C10—Cl31.781 (2)
C5—C61.409 (2)C10—H10A0.9700
C5—C71.462 (2)C10—H10B0.9700
C6—H60.9300N1—H1N0.874 (19)
C7—N11.290 (2)O1—H1O0.827 (19)
C6—C1—C2121.53 (17)C7—C8—H8B109.5
C6—C1—Cl1119.55 (15)H8A—C8—H8B109.5
C2—C1—Cl1118.92 (15)C7—C8—H8C109.5
C3—C2—C1118.94 (17)H8A—C8—H8C109.5
C3—C2—H2120.5H8B—C8—H8C109.5
C1—C2—H2120.5N1—C9—C10110.83 (15)
C2—C3—C4122.61 (16)N1—C9—H9A109.5
C2—C3—Cl2119.69 (14)C10—C9—H9A109.5
C4—C3—Cl2117.69 (13)N1—C9—H9B109.5
O1—C4—C3120.31 (15)C10—C9—H9B109.5
O1—C4—C5122.71 (15)H9A—C9—H9B108.1
C3—C4—C5116.98 (15)C9—C10—Cl3112.06 (12)
C6—C5—C4119.49 (16)C9—C10—H10A109.2
C6—C5—C7120.94 (15)Cl3—C10—H10A109.2
C4—C5—C7119.56 (15)C9—C10—H10B109.2
C1—C6—C5120.43 (17)Cl3—C10—H10B109.2
C1—C6—H6119.8H10A—C10—H10B107.9
C5—C6—H6119.8C7—N1—C9124.26 (15)
N1—C7—C5116.87 (14)C7—N1—H1N113 (3)
N1—C7—C8121.32 (16)C9—N1—H1N122 (3)
C5—C7—C8121.82 (16)C4—O1—H1O112 (4)
C7—C8—H8A109.5
C6—C1—C2—C30.2 (3)C2—C1—C6—C5−1.1 (3)
Cl1—C1—C2—C3179.64 (14)Cl1—C1—C6—C5179.53 (13)
C1—C2—C3—C41.1 (3)C4—C5—C6—C10.5 (3)
C1—C2—C3—Cl2−177.60 (14)C7—C5—C6—C1−179.91 (16)
C2—C3—C4—O1178.66 (16)C6—C5—C7—N1177.17 (15)
Cl2—C3—C4—O1−2.6 (2)C4—C5—C7—N1−3.3 (2)
C2—C3—C4—C5−1.6 (3)C6—C5—C7—C8−3.0 (3)
Cl2—C3—C4—C5177.17 (12)C4—C5—C7—C8176.56 (16)
O1—C4—C5—C6−179.54 (15)N1—C9—C10—Cl360.56 (18)
C3—C4—C5—C60.7 (2)C5—C7—N1—C9179.36 (15)
O1—C4—C5—C70.9 (3)C8—C7—N1—C9−0.5 (3)
C3—C4—C5—C7−178.81 (15)C10—C9—N1—C7177.78 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.88 (2)1.68 (2)2.479 (2)150 (4)
C10—H10B···O1i0.972.483.416 (2)159
C10—H10A···Cl3ii0.972.863.621 (2)136
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC10H10Cl3NO
Mr266.54
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)14.5710 (2), 10.2323 (2), 7.7384 (1)
β (°) 94.376 (1)
V (Å3)1150.39 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.77
Crystal size (mm)0.38 × 0.19 × 0.07
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.762, 0.951
No. of measured, independent and
observed [I > 2σ(I)] reflections		8253, 2625, 1940
Rint0.023
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.091, 1.02
No. of reflections2625
No. of parameters146
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.25, −0.21

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.88 (2)1.68 (2)2.479 (2)150 (4)
C10—H10B···O1i0.972.483.416 (2)159
C10—H10A···Cl3ii0.972.863.621 (2)136
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2.
 

Acknowledgements

This study was supported by the Natural Science Foundation of Shandong Province (Z2008B10).

References

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3106
https://doi.org/10.1107/S160053681004448X
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