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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page m1894
https://doi.org/10.1107/S1600536811050690

Di­chloridobis(4-methyl-3,5-di­phenyl-1H-pyrazole-κN2)copper(II)

Moayad Hossaini Sadra* and Behzad Soltanib

aResearch Institute for Fundamental Sciences (RIFS), University of Tabriz, 51664, Tabriz, Iran, and bDepartment of Chemistry, Azarbaijan University of Tarbiat Moallem, Tabriz, Iran
*Correspondence e-mail: hosainis@yahoo.com

(Received 3 November 2011; accepted 25 November 2011; online 30 November 2011)

The asymmetric unit of the title compound, [CuCl2(C16H14N2)2], comprises half of the complex. The CuII atom lies on a crystallographic twofold rotation axis and shows a significantly distorted tetra­hedral coordination geometry. The dihedral angle between the phenyl rings is 74.3 (2)°. The crystal structure is stabilized by inter­molecular π–π inter­actions [centroid–centroid distances = 3.635 (2)–3.803 (3) Å].

Related literature

For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For background to pyrazole chemistry, see: Mukherjee (2000[Mukherjee, R. (2000). Coord. Chem. Rev. 203, 151-170.]); Mukherjee & Sarka (2003[Mukherjee, R. & Sarka, A. (2003). ARKIVOC, ix, 87-90.]); Hossaini Sadr et al. (2004[Hossaini Sadr, M., Clegg, W. & Bijhanzade, H. R. (2004). Polyhedron, 23, 637-641.], 2005[Hossaini Sadr, M., Jalili, A. R., Razmi, H. & Seik Weng, N. (2005). J. Organomet. Chem. 690, 2128-2132.]).

[Scheme 1]

Experimental

Crystal data

  • [CuCl2(C16H14N2)2]

  • Mr = 603.03

  • Monoclinic, C 2/c

  • a = 19.105 (4) Å

  • b = 8.5062 (17) Å

  • c = 17.399 (4) Å

  • β = 99.39 (3)°

  • V = 2789.6 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.00 mm−1

  • T = 120 K

  • 0.23 × 0.09 × 0.03 mm
Data collection

  • Stoe IPDS II Image Plate diffractometer

  • Absorption correction: numerical (X-RED; Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]) Tmin = 0.895, Tmax = 0.970

  • 9857 measured reflections

  • 3752 independent reflections

  • 3026 reflections with I > 2σ(I)

  • Rint = 0.119
Refinement

  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 0.215

  • S = 1.11

  • 3752 reflections

  • 181 parameters

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

  • Δρmax = 0.87 e Å−3

  • Δρmin = −0.76 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811050690/rz2665sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050690/rz2665Isup2.hkl

checkCIF report


Comment top

There are a lot of publications on coordination chemistry of pyrazole-based chelating ligands which present versatile coordination geometry and nuclearity (Mukherjee, 2000; Mukherjee & Sarka, 2003). The suitable structure and high stability of pyrazoles, in addition to the ability of their deprotonated form to act as powerful nucleophiles in substitution reactions, have made them good candidates for incorporation in the design of new ligands. The easy control of the electronic and steric properties of the pyrazolyl-derived ligands by introducing different substituents in the pyrazolyl rings is another advantage and expands the domain of pyrazole-type ligands. As part of a general study of pyrazole ligands (Hossaini Sadr et al., 2005; Hossaini Sadr et al., 2004), we have determined the crystal structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises half of the complex. The copper(II) atom lies on a crystallographic two-fold rotation axis and shows a significantly distorted tetrahedral coordination geometry. The dihedral angle between the phenyl rings is 74.3 (2)°. The crystal structure is stabilized by intermolecular π-π interactions [Cg1···Cg2i = 3.635 (2)Å, Cg3···Cg3ii = 3.803 (3)Å; Cg1, Cg2 and Cg3 are centroids of the N1/N2/C10/C8/C7, C1–C6, and C11–C16 rings, respectively; symmetry codes: (i) 1-x, y, 1/2-z, (ii) 1/2-x, 1/2-y, -z].

Related literature top

For standard bond lengths, see: Allen et al. (1987). For background to pyrazole chemistry, see: Mukherjee (2000); Mukherjee & Sarka (2003); Hossaini Sadr et al. (2004, 2005).

Experimental top

The title compound was synthesized by adding dry CuCl2 (1 mmol, 134 mg) to a solution of 4-methyl-3,5-diphenyl-1H-pyrazole (2 mmol, 468 mg) in THF (30 ml). The mixture was stirred for 12 hour. The resultant yellow solution was filtered and the solid phase washed by ether and dried in vacuo. Orange single crystals of the title compound suitable for X-ray structure determination were recrystallized from acethonitrile by slow evaporation of the solvent at room temperature over several days.

Refinement top

The N-bound atoms was located in a difference Fourier map and refined freely. All other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.96 Å and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms.

Structure description top

There are a lot of publications on coordination chemistry of pyrazole-based chelating ligands which present versatile coordination geometry and nuclearity (Mukherjee, 2000; Mukherjee & Sarka, 2003). The suitable structure and high stability of pyrazoles, in addition to the ability of their deprotonated form to act as powerful nucleophiles in substitution reactions, have made them good candidates for incorporation in the design of new ligands. The easy control of the electronic and steric properties of the pyrazolyl-derived ligands by introducing different substituents in the pyrazolyl rings is another advantage and expands the domain of pyrazole-type ligands. As part of a general study of pyrazole ligands (Hossaini Sadr et al., 2005; Hossaini Sadr et al., 2004), we have determined the crystal structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises half of the complex. The copper(II) atom lies on a crystallographic two-fold rotation axis and shows a significantly distorted tetrahedral coordination geometry. The dihedral angle between the phenyl rings is 74.3 (2)°. The crystal structure is stabilized by intermolecular π-π interactions [Cg1···Cg2i = 3.635 (2)Å, Cg3···Cg3ii = 3.803 (3)Å; Cg1, Cg2 and Cg3 are centroids of the N1/N2/C10/C8/C7, C1–C6, and C11–C16 rings, respectively; symmetry codes: (i) 1-x, y, 1/2-z, (ii) 1/2-x, 1/2-y, -z].

For standard bond lengths, see: Allen et al. (1987). For background to pyrazole chemistry, see: Mukherjee (2000); Mukherjee & Sarka (2003); Hossaini Sadr et al. (2004, 2005).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); 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: PLATON (Spek, 2009) and SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. Unlabelled atoms are related to the labelled atoms by the symmetry operation 1-x, y, 1/2-z.
Dichloridobis(4-methyl-3,5-diphenyl-1H-pyrazole-κN2)copper(II) top
Crystal data top
[CuCl2(C16H14N2)2]F(000) = 1244
Mr = 603.03Dx = 1.436 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2500 reflections
a = 19.105 (4) Åθ = 2.5–28.4°
b = 8.5062 (17) ŵ = 1.00 mm−1
c = 17.399 (4) ÅT = 120 K
β = 99.39 (3)°Needle, orange
V = 2789.6 (11) Å30.23 × 0.09 × 0.03 mm
Z = 4
Data collection top
Stoe IPDS II Image Plate
diffractometer		3752 independent reflections
Radiation source: fine-focus sealed tube3026 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.119
Detector resolution: 0.15 mm pixels mm-1θmax = 29.3°, θmin = 2.2°
rotation method scansh = −26→26
Absorption correction: numerical
(X-RED; Stoe & Cie, 2005)		k = −11→10
Tmin = 0.895, Tmax = 0.970l = −23→21
9857 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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.215H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0975P)2 + 21.982P]
where P = (Fo2 + 2Fc2)/3
3752 reflections(Δ/σ)max = 0.004
181 parametersΔρmax = 0.87 e Å−3
0 restraintsΔρmin = −0.76 e Å−3
Crystal data top
[CuCl2(C16H14N2)2]V = 2789.6 (11) Å3
Mr = 603.03Z = 4
Monoclinic, C2/cMo Kα radiation
a = 19.105 (4) ŵ = 1.00 mm−1
b = 8.5062 (17) ÅT = 120 K
c = 17.399 (4) Å0.23 × 0.09 × 0.03 mm
β = 99.39 (3)°
Data collection top
Stoe IPDS II Image Plate
diffractometer		3752 independent reflections
Absorption correction: numerical
(X-RED; Stoe & Cie, 2005)		3026 reflections with I > 2σ(I)
Tmin = 0.895, Tmax = 0.970Rint = 0.119
9857 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0740 restraints
wR(F2) = 0.215H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0975P)2 + 21.982P]
where P = (Fo2 + 2Fc2)/3
3752 reflectionsΔρmax = 0.87 e Å−3
181 parametersΔρmin = −0.76 e Å−3
Special details top

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 > 2sigma(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
C10.6094 (2)0.2678 (5)0.1486 (2)0.0166 (8)
H10.59090.17420.12620.020*
C20.6825 (2)0.2881 (6)0.1666 (2)0.0202 (8)
H2A0.71270.20850.15560.024*
C30.7105 (2)0.4266 (6)0.2009 (3)0.0232 (9)
H30.75930.44000.21280.028*
C40.6652 (2)0.5450 (5)0.2173 (3)0.0209 (8)
H40.68400.63720.24090.025*
C50.5920 (2)0.5271 (5)0.1986 (2)0.0172 (8)
H50.56200.60770.20900.021*
C60.5637 (2)0.3877 (5)0.1641 (2)0.0141 (7)
C70.4861 (2)0.3647 (5)0.1464 (2)0.0136 (7)
C80.4328 (2)0.4585 (5)0.1020 (2)0.0142 (7)
C90.4448 (2)0.6123 (5)0.0636 (3)0.0209 (8)
H9A0.41960.69420.08540.025*
H9B0.42790.60470.00870.025*
H9C0.49460.63610.07220.025*
C100.3698 (2)0.3785 (5)0.1048 (2)0.0144 (7)
C110.2955 (2)0.4125 (5)0.0719 (2)0.0145 (7)
C120.2782 (2)0.5123 (6)0.0082 (3)0.0203 (8)
H120.31430.5577−0.01420.024*
C130.2076 (2)0.5455 (6)−0.0226 (3)0.0222 (9)
H130.19690.6130−0.06490.027*
C140.1534 (2)0.4775 (6)0.0101 (3)0.0222 (9)
H140.10630.4996−0.01020.027*
C150.1695 (2)0.3761 (6)0.0734 (3)0.0234 (9)
H150.13330.32890.09480.028*
C160.2401 (2)0.3455 (5)0.1044 (3)0.0192 (8)
H160.25060.27960.14740.023*
N10.45725 (17)0.2358 (4)0.17249 (19)0.0136 (6)
N20.38684 (17)0.2464 (4)0.1472 (2)0.0148 (6)
H2B0.357 (3)0.167 (6)0.150 (3)0.006 (11)*
Cl10.40945 (5)−0.09017 (12)0.21857 (7)0.0219 (3)
Cu10.50000.07621 (8)0.25000.0124 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0159 (17)0.0188 (19)0.0153 (17)0.0016 (15)0.0030 (14)0.0001 (15)
C20.0189 (19)0.026 (2)0.0158 (18)0.0058 (16)0.0036 (15)0.0032 (16)
C30.0146 (17)0.034 (2)0.022 (2)−0.0001 (17)0.0041 (15)0.0062 (19)
C40.0183 (18)0.019 (2)0.026 (2)−0.0081 (16)0.0056 (16)0.0016 (16)
C50.0161 (17)0.0172 (19)0.0182 (19)−0.0008 (14)0.0026 (14)−0.0008 (15)
C60.0112 (15)0.0173 (18)0.0142 (17)0.0011 (13)0.0029 (13)0.0014 (14)
C70.0120 (16)0.0168 (18)0.0124 (17)0.0000 (14)0.0031 (13)−0.0017 (14)
C80.0154 (16)0.0149 (17)0.0123 (16)0.0044 (14)0.0026 (13)0.0030 (14)
C90.0194 (19)0.0184 (19)0.025 (2)0.0036 (15)0.0048 (16)0.0115 (16)
C100.0120 (16)0.0172 (18)0.0131 (17)0.0047 (14)−0.0007 (13)0.0016 (14)
C110.0133 (16)0.0137 (17)0.0151 (17)0.0030 (13)−0.0019 (13)−0.0022 (14)
C120.0175 (18)0.023 (2)0.020 (2)−0.0010 (16)0.0008 (15)−0.0013 (16)
C130.023 (2)0.024 (2)0.0174 (19)0.0049 (17)−0.0039 (15)0.0009 (16)
C140.0146 (17)0.028 (2)0.021 (2)0.0052 (16)−0.0052 (15)−0.0081 (17)
C150.0174 (19)0.026 (2)0.027 (2)0.0030 (16)0.0034 (16)0.0011 (18)
C160.0170 (18)0.020 (2)0.0205 (19)0.0006 (15)0.0035 (15)−0.0003 (16)
N10.0135 (14)0.0122 (15)0.0147 (15)0.0021 (12)0.0013 (12)0.0027 (12)
N20.0120 (14)0.0134 (15)0.0185 (16)−0.0021 (12)0.0009 (12)−0.0020 (13)
Cl10.0168 (5)0.0149 (5)0.0316 (6)−0.0044 (3)−0.0034 (4)0.0033 (4)
Cu10.0114 (3)0.0098 (3)0.0148 (3)0.000−0.0016 (2)0.000
Geometric parameters (Å, º) top
C1—C21.391 (6)C10—N21.355 (5)
C1—C61.397 (5)C10—C111.471 (5)
C1—H10.9300C11—C121.392 (6)
C2—C31.388 (7)C11—C161.399 (6)
C2—H2A0.9300C12—C131.397 (6)
C3—C41.387 (7)C12—H120.9300
C3—H30.9300C13—C141.386 (7)
C4—C51.393 (6)C13—H130.9300
C4—H40.9300C14—C151.393 (7)
C5—C61.397 (6)C14—H140.9300
C5—H50.9300C15—C161.393 (6)
C6—C71.477 (5)C15—H150.9300
C7—N11.340 (5)C16—H160.9300
C7—C81.418 (5)N1—N21.348 (5)
C8—C101.391 (6)N1—Cu11.992 (3)
C8—C91.503 (6)N2—H2B0.90 (5)
C9—H9A0.9600Cl1—Cu12.2329 (11)
C9—H9B0.9600Cu1—N1i1.992 (3)
C9—H9C0.9600Cu1—Cl1i2.2329 (11)
C2—C1—C6120.1 (4)C8—C10—C11132.6 (4)
C2—C1—H1119.9C12—C11—C16118.3 (4)
C6—C1—H1119.9C12—C11—C10121.2 (4)
C3—C2—C1120.3 (4)C16—C11—C10120.6 (4)
C3—C2—H2A119.9C11—C12—C13121.1 (4)
C1—C2—H2A119.9C11—C12—H12119.4
C4—C3—C2119.7 (4)C13—C12—H12119.4
C4—C3—H3120.1C14—C13—C12119.8 (4)
C2—C3—H3120.1C14—C13—H13120.1
C3—C4—C5120.6 (4)C12—C13—H13120.1
C3—C4—H4119.7C13—C14—C15119.9 (4)
C5—C4—H4119.7C13—C14—H14120.0
C4—C5—C6119.8 (4)C15—C14—H14120.0
C4—C5—H5120.1C14—C15—C16119.9 (4)
C6—C5—H5120.1C14—C15—H15120.1
C5—C6—C1119.5 (4)C16—C15—H15120.1
C5—C6—C7120.5 (4)C15—C16—C11121.0 (4)
C1—C6—C7120.0 (4)C15—C16—H16119.5
N1—C7—C8110.3 (3)C11—C16—H16119.5
N1—C7—C6119.4 (4)C7—N1—N2106.1 (3)
C8—C7—C6130.2 (4)C7—N1—Cu1129.9 (3)
C10—C8—C7104.7 (3)N2—N1—Cu1122.9 (3)
C10—C8—C9129.6 (4)N1—N2—C10111.8 (3)
C7—C8—C9125.7 (4)N1—N2—H2B123 (3)
C8—C9—H9A109.5C10—N2—H2B124 (3)
C8—C9—H9B109.5N1i—Cu1—N194.1 (2)
H9A—C9—H9B109.5N1i—Cu1—Cl1144.42 (10)
C8—C9—H9C109.5N1—Cu1—Cl192.88 (10)
H9A—C9—H9C109.5N1i—Cu1—Cl1i92.88 (10)
H9B—C9—H9C109.5N1—Cu1—Cl1i144.42 (10)
N2—C10—C8107.0 (3)Cl1—Cu1—Cl1i101.34 (6)
N2—C10—C11120.4 (4)
C6—C1—C2—C30.8 (6)C8—C10—C11—C16−157.4 (5)
C1—C2—C3—C40.0 (7)C16—C11—C12—C130.2 (7)
C2—C3—C4—C5−0.9 (7)C10—C11—C12—C13−179.5 (4)
C3—C4—C5—C61.0 (7)C11—C12—C13—C14−0.5 (7)
C4—C5—C6—C1−0.2 (6)C12—C13—C14—C15−0.2 (7)
C4—C5—C6—C7177.9 (4)C13—C14—C15—C161.1 (7)
C2—C1—C6—C5−0.7 (6)C14—C15—C16—C11−1.4 (7)
C2—C1—C6—C7−178.8 (4)C12—C11—C16—C150.8 (6)
C5—C6—C7—N1−127.0 (4)C10—C11—C16—C15−179.5 (4)
C1—C6—C7—N151.1 (5)C8—C7—N1—N2−1.2 (4)
C5—C6—C7—C854.9 (6)C6—C7—N1—N2−179.6 (3)
C1—C6—C7—C8−127.0 (5)C8—C7—N1—Cu1−169.6 (3)
N1—C7—C8—C101.3 (4)C6—C7—N1—Cu112.0 (5)
C6—C7—C8—C10179.5 (4)C7—N1—N2—C100.6 (4)
N1—C7—C8—C9179.7 (4)Cu1—N1—N2—C10170.1 (3)
C6—C7—C8—C9−2.1 (7)C8—C10—N2—N10.2 (5)
C7—C8—C10—N2−0.9 (4)C11—C10—N2—N1−179.8 (3)
C9—C8—C10—N2−179.2 (4)C7—N1—Cu1—N1i47.2 (3)
C7—C8—C10—C11179.2 (4)N2—N1—Cu1—N1i−119.6 (3)
C9—C8—C10—C110.9 (8)C7—N1—Cu1—Cl1−167.7 (3)
N2—C10—C11—C12−157.6 (4)N2—N1—Cu1—Cl125.5 (3)
C8—C10—C11—C1222.3 (7)C7—N1—Cu1—Cl1i−53.6 (4)
N2—C10—C11—C1622.7 (6)N2—N1—Cu1—Cl1i139.6 (2)
Symmetry code: (i) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula[CuCl2(C16H14N2)2]
Mr603.03
Crystal system, space groupMonoclinic, C2/c
Temperature (K)120
a, b, c (Å)19.105 (4), 8.5062 (17), 17.399 (4)
β (°) 99.39 (3)
V (Å3)2789.6 (11)
Z4
Radiation typeMo Kα
µ (mm−1)1.00
Crystal size (mm)0.23 × 0.09 × 0.03
Data collection
DiffractometerStoe IPDS II Image Plate
Absorption correctionNumerical
(X-RED; Stoe & Cie, 2005)
Tmin, Tmax0.895, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections		9857, 3752, 3026
Rint0.119
(sin θ/λ)max (Å−1)0.688
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.215, 1.11
No. of reflections3752
No. of parameters181
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(Fo2) + (0.0975P)2 + 21.982P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å−3)0.87, −0.76

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the Research Institute for Fundamental Sciences (RIFS), University of Tabriz, through grant No. 31.2847.

References

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page m1894
https://doi.org/10.1107/S1600536811050690
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