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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 9| September 2010| Page o2218
https://doi.org/10.1107/S1600536810030382

5-tert-Butyl-2-hy­dr­oxy-3-(2-thien­yl)benzaldehyde

Yanwei Wang,a Zhenzhen Qiua and Hongze Lianga*

aFaculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
*Correspondence e-mail: lianghongze@nbu.edu.cn

(Received 14 July 2010; accepted 30 July 2010; online 4 August 2010)

In the crystal structure of the title compound, C15H16O2S, the thio­phene ring is essentially planar (r.m.s. deviation = 0.006 Å for all non-H atoms) and roughly coplanar with the benzene ring, the dihedral angle between the mean planes of the rings being 4.35 (8)°. An intra­molecular O—H⋯O hydrogen bond is observed between the OH group and the aldehyde O atom.

Related literature

For related salicyl­aldehyde derivative compounds, see: Qiu et al. (2009[Qiu, L., Lin, J. & Xu, Y. (2009). Inorg. Chem. Commun. 12, 986-989.]); Yu et al. (2007[Yu, T.-Z., Su, W.-M., Li, W.-L., Hong, Z.-R., Hua, R.-N. & Li, B. (2007). Thin Solid Films, 515, 4080-4084.]); Wang et al. (2009[Wang, H., Zhang, D., Ni, Z.-H., Li, X., Tian, L. & Jiang, J. (2009). Inorg. Chem. 48, 5946-5956.]); Wong et al. (2004[Wong, W.-K., Liang, H., Guo, J., Wong, W.-Y., Lo, W.-K., Li, K.-F., Cheah, K.-W., Zhou, Z. & Wong, W.-T. (2004). Eur. J. Inorg. Chem. 4, 829-836.]).

[Scheme 1]

Experimental

Crystal data

  • C15H16O2S

  • Mr = 260.34

  • Triclinic, [P \overline 1]

  • a = 7.2016 (14) Å

  • b = 8.9375 (18) Å

  • c = 10.922 (2) Å

  • α = 91.50 (3)°

  • β = 107.69 (3)°

  • γ = 93.25 (3)°

  • V = 668.0 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.23 mm−1

  • T = 173 K

  • 0.10 × 0.10 × 0.10 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.977, Tmax = 0.977

  • 5891 measured reflections

  • 2705 independent reflections

  • 1958 reflections with I > 2σ(I)

  • Rint = 0.020
Refinement

  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.208

  • S = 1.15

  • 2705 reflections

  • 179 parameters

  • 9 restraints

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

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2D⋯O1 0.78 (3) 1.89 (3) 2.623 (3) 157 (3)

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810030382/zq2050sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030382/zq2050Isup2.hkl

checkCIF report


Comment top

Salicylaldehyde and its derivatives are widely used in the construction of metal complexes (Qiu et al., 2009; Wang et al., 2009; Yu et al., 2007). We have synthesized a series of lanthanide complexes of a Schiff base which derived from 2-pyridyl salicylaldehyde and investigated their luminescent properties (Wong et al., 2004). In the course of exploring new luminescent compounds, we synthesized the title molecule 5-tert-butyl-2-hydroxy-3-thiophen-2-ylbenzaldehyde (I) as an intermediate compound.

The molecular structure of the title compound is shown in Fig. 1. The thiophene ring is essentially planar (rms deviation = 0.006Å for all non-H atoms) and roughly coplanar with the phenyl ring, making a dihedral angle between the mean planes of the rings of 4.35 (8)°. There are no intermolecular hydrogen bonds in the crystal structure but the intramolecular interaction O2—H2D···O1 between the hydroxy OH group and the aldehyde O atom is helpful to stabilize the molecular conformation.

Related literature top

For related salicylaldehyde derivative compounds, see: Qiu et al. (2009); Yu et al. (2007); Wang et al. (2009). For the luminescent properties of lanthanide complexes, see: Wong et al. (2004).

Experimental top

3-Bromo-5-tert-butyl-2-hydroxybenzaldehyde (1.50 g, 5.86 mmol), 2-thienyl-tributyltin (2.40 g, 6.45 mmol), triphenyl phosphine (0.31 g, 0.38 mmol) and palladium dichloride (0.05 g, 0.28 mmol) were added to 20 ml THF in a round flask, and this mixture was refluxed with agitation for 24 h. Then, 20 ml toluene was added and the mixture was refluxed at 100°C for another 24 h. Finally, the reaction mixture was refluxed at 105°C after addition of 20 ml DMF for further 24 h. After evaporating the solvent, the residue was chromatographed on silica gel and a yellowish precipitate was produced. The precipitate was recrystallized from dichloromethane and yellow block-shaped crystals were obtained (0.62 g, 41%). 1H NMR (400 MHz, CDCl3): 11.73 (s, 1H), 9.93 (s, 1H), 7.91 (d, J = 2.0 Hz, 1H), 7.31 (dd, J = 1.2 Hz, J = 3.6 Hz,1H), 7.48 (d, J = 2.4 Hz, 1H), 7.37 (dd, J = 4.8 Hz, J = 0.8 Hz, 1H), 7.25 (s, 1H), 7.13 (dd, J = 3.6 Hz, J = 4.8 Hz, 1H), 1.37 (s, 9H). MS (EI, m/z): 260[M]+

Refinement top

The H atoms attached to C atoms were placed in calculated positions and treated using a riding-model approximation (with C–H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms, and with C–H = 0.98 Å and Uiso(H) = 1.5Ueq(C) for the methyl H atoms). The important H atoms bonded to O2 and C6 were located in the difference Fourier map and were freely refined.

Structure description top

Salicylaldehyde and its derivatives are widely used in the construction of metal complexes (Qiu et al., 2009; Wang et al., 2009; Yu et al., 2007). We have synthesized a series of lanthanide complexes of a Schiff base which derived from 2-pyridyl salicylaldehyde and investigated their luminescent properties (Wong et al., 2004). In the course of exploring new luminescent compounds, we synthesized the title molecule 5-tert-butyl-2-hydroxy-3-thiophen-2-ylbenzaldehyde (I) as an intermediate compound.

The molecular structure of the title compound is shown in Fig. 1. The thiophene ring is essentially planar (rms deviation = 0.006Å for all non-H atoms) and roughly coplanar with the phenyl ring, making a dihedral angle between the mean planes of the rings of 4.35 (8)°. There are no intermolecular hydrogen bonds in the crystal structure but the intramolecular interaction O2—H2D···O1 between the hydroxy OH group and the aldehyde O atom is helpful to stabilize the molecular conformation.

For related salicylaldehyde derivative compounds, see: Qiu et al. (2009); Yu et al. (2007); Wang et al. (2009). For the luminescent properties of lanthanide complexes, see: Wong et al. (2004).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of (I) with displacement ellipsoids drawn at the 30% probability level. The dotted line indicates the intramolecular H-bond.
5-tert-Butyl-2-hydroxy-3-(2-thienyl)benzaldehyde top
Crystal data top
C15H16O2SZ = 2
Mr = 260.34F(000) = 276
Triclinic, P1Dx = 1.294 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2016 (14) ÅCell parameters from 5891 reflections
b = 8.9375 (18) Åθ = 3.0–26.4°
c = 10.922 (2) ŵ = 0.23 mm−1
α = 91.50 (3)°T = 173 K
β = 107.69 (3)°Block, yellow
γ = 93.25 (3)°0.10 × 0.10 × 0.10 mm
V = 668.0 (2) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2705 independent reflections
Radiation source: fine-focus sealed tube1958 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 0 pixels mm-1θmax = 26.4°, θmin = 3.0°
ω scansh = −8→8
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −11→11
Tmin = 0.977, Tmax = 0.977l = −13→13
5891 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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208H atoms treated by a mixture of independent and constrained refinement
S = 1.15 w = 1/[σ2(Fo2) + (0.1265P)2 + 0.0566P]
where P = (Fo2 + 2Fc2)/3
2705 reflections(Δ/σ)max < 0.001
179 parametersΔρmax = 0.41 e Å−3
9 restraintsΔρmin = −0.45 e Å−3
Crystal data top
C15H16O2Sγ = 93.25 (3)°
Mr = 260.34V = 668.0 (2) Å3
Triclinic, P1Z = 2
a = 7.2016 (14) ÅMo Kα radiation
b = 8.9375 (18) ŵ = 0.23 mm−1
c = 10.922 (2) ÅT = 173 K
α = 91.50 (3)°0.10 × 0.10 × 0.10 mm
β = 107.69 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2705 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		1958 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.977Rint = 0.020
5891 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0599 restraints
wR(F2) = 0.208H atoms treated by a mixture of independent and constrained refinement
S = 1.15Δρmax = 0.41 e Å−3
2705 reflectionsΔρmin = −0.45 e Å−3
179 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
S10.39900 (12)0.44272 (9)0.30990 (6)0.0798 (4)
O20.3088 (3)0.6482 (2)0.12395 (19)0.0677 (5)
C150.2702 (3)0.3967 (2)0.0406 (2)0.0482 (5)
C140.2152 (3)0.3004 (2)−0.0692 (2)0.0496 (5)
H14A0.22260.1957−0.05740.060*
C130.1403 (3)0.4992 (3)−0.2105 (2)0.0544 (6)
H13A0.09790.5352−0.29490.065*
C120.3408 (3)0.3350 (3)0.1694 (2)0.0508 (5)
C110.1504 (3)0.3476 (2)−0.1946 (2)0.0497 (5)
C100.2573 (3)0.5507 (3)0.0206 (2)0.0507 (5)
C90.1912 (3)0.6013 (3)−0.1048 (2)0.0556 (6)
C80.0927 (4)0.2304 (3)−0.3084 (2)0.0564 (6)
C70.3726 (4)0.1835 (3)0.1953 (2)0.0636 (6)
O10.2186 (4)0.8609 (2)−0.0407 (2)0.0947 (7)
C60.1769 (5)0.7611 (3)−0.1262 (3)0.0748 (8)
C50.4400 (4)0.1649 (3)0.3312 (3)0.0721 (7)
H5A0.46880.07060.36820.087*
C40.2655 (4)0.1362 (3)−0.3025 (2)0.0716 (7)
H4A0.37630.2017−0.30800.107*
H4B0.22830.0616−0.37460.107*
H4C0.30260.0851−0.22120.107*
C30.0331 (5)0.3042 (3)−0.4383 (2)0.0759 (8)
H3A0.14250.3700−0.44560.114*
H3B−0.07950.3635−0.44460.114*
H3C−0.00170.2265−0.50790.114*
C2−0.0816 (4)0.1276 (3)−0.2998 (3)0.0757 (8)
H2A−0.11910.0532−0.37210.114*
H2B−0.19220.1881−0.30320.114*
H2C−0.04430.0761−0.21870.114*
C10.4584 (4)0.2933 (4)0.4010 (3)0.0765 (8)
H70.354 (6)0.109 (3)0.140 (3)0.127 (14)*
H20.504 (4)0.303 (4)0.4875 (10)0.082 (9)*
H6A0.135 (6)0.804 (5)−0.213 (4)0.127 (14)*
H2D0.292 (4)0.726 (4)0.093 (3)0.068 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.1003 (6)0.0763 (6)0.0558 (5)0.0081 (4)0.0148 (4)−0.0179 (3)
O20.0845 (13)0.0497 (11)0.0657 (11)−0.0018 (9)0.0210 (10)−0.0186 (9)
C150.0443 (11)0.0505 (12)0.0496 (11)−0.0004 (9)0.0157 (9)−0.0095 (9)
C140.0550 (12)0.0418 (11)0.0503 (12)0.0017 (9)0.0146 (10)−0.0067 (9)
C130.0561 (13)0.0525 (13)0.0551 (12)0.0022 (10)0.0183 (10)−0.0028 (10)
C120.0469 (11)0.0555 (13)0.0485 (11)−0.0001 (9)0.0142 (9)−0.0107 (9)
C110.0525 (12)0.0471 (12)0.0487 (11)0.0010 (9)0.0155 (9)−0.0064 (9)
C100.0485 (11)0.0472 (12)0.0572 (12)−0.0019 (9)0.0197 (10)−0.0134 (9)
C90.0594 (13)0.0449 (12)0.0653 (14)−0.0011 (10)0.0245 (11)−0.0063 (10)
C80.0670 (14)0.0505 (13)0.0484 (12)0.0005 (10)0.0144 (10)−0.0097 (9)
C70.0820 (15)0.0581 (13)0.0452 (11)0.0039 (11)0.0118 (10)0.0004 (9)
O10.141 (2)0.0451 (11)0.0976 (15)−0.0011 (11)0.0388 (14)−0.0120 (10)
C60.098 (2)0.0475 (14)0.0825 (19)0.0032 (13)0.0332 (17)−0.0002 (13)
C50.0849 (15)0.0702 (14)0.0555 (11)0.0096 (12)0.0121 (11)0.0049 (10)
C40.0867 (19)0.0661 (16)0.0595 (14)0.0129 (13)0.0186 (13)−0.0165 (12)
C30.100 (2)0.0675 (17)0.0505 (13)0.0057 (15)0.0103 (13)−0.0100 (12)
C20.0847 (19)0.0693 (17)0.0667 (16)−0.0170 (14)0.0193 (14)−0.0210 (13)
C10.0772 (18)0.097 (2)0.0504 (14)0.0074 (15)0.0124 (13)−0.0067 (14)
Geometric parameters (Å, º) top
S1—C11.683 (3)C8—C21.541 (4)
S1—C121.716 (2)C7—C51.432 (3)
O2—C101.352 (3)C7—H70.867 (10)
O2—H2D0.78 (3)O1—C61.230 (3)
C15—C141.399 (3)C6—H6A0.99 (4)
C15—C101.402 (3)C5—C11.339 (4)
C15—C121.476 (3)C5—H5A0.9500
C14—C111.391 (3)C4—H4A0.9800
C14—H14A0.9500C4—H4B0.9800
C13—C111.374 (3)C4—H4C0.9800
C13—C91.396 (3)C3—H3A0.9800
C13—H13A0.9500C3—H3B0.9800
C12—C71.408 (3)C3—H3C0.9800
C11—C81.544 (3)C2—H2A0.9800
C10—C91.403 (3)C2—H2B0.9800
C9—C61.457 (4)C2—H2C0.9800
C8—C41.527 (4)C1—H20.902 (10)
C8—C31.530 (4)
C1—S1—C1292.60 (13)C12—C7—H7127 (3)
C10—O2—H2D103 (2)C5—C7—H7122 (3)
C14—C15—C10116.7 (2)O1—C6—C9125.0 (3)
C14—C15—C12120.00 (19)O1—C6—H6A111 (2)
C10—C15—C12123.30 (19)C9—C6—H6A124 (3)
C11—C14—C15124.4 (2)C1—C5—C7113.4 (3)
C11—C14—H14A117.8C1—C5—H5A123.3
C15—C14—H14A117.8C7—C5—H5A123.3
C11—C13—C9121.2 (2)C8—C4—H4A109.5
C11—C13—H13A119.4C8—C4—H4B109.5
C9—C13—H13A119.4H4A—C4—H4B109.5
C7—C12—C15125.95 (19)C8—C4—H4C109.5
C7—C12—S1110.58 (17)H4A—C4—H4C109.5
C15—C12—S1123.46 (17)H4B—C4—H4C109.5
C13—C11—C14117.3 (2)C8—C3—H3A109.5
C13—C11—C8123.0 (2)C8—C3—H3B109.5
C14—C11—C8119.69 (19)H3A—C3—H3B109.5
O2—C10—C15118.8 (2)C8—C3—H3C109.5
O2—C10—C9121.1 (2)H3A—C3—H3C109.5
C15—C10—C9120.13 (19)H3B—C3—H3C109.5
C13—C9—C10120.3 (2)C8—C2—H2A109.5
C13—C9—C6119.3 (2)C8—C2—H2B109.5
C10—C9—C6120.3 (2)H2A—C2—H2B109.5
C4—C8—C3108.3 (2)C8—C2—H2C109.5
C4—C8—C2109.5 (2)H2A—C2—H2C109.5
C3—C8—C2108.3 (2)H2B—C2—H2C109.5
C4—C8—C11109.58 (19)C5—C1—S1112.9 (2)
C3—C8—C11111.9 (2)C5—C1—H2125 (2)
C2—C8—C11109.16 (19)S1—C1—H2122 (2)
C12—C7—C5110.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2D···O10.78 (3)1.89 (3)2.623 (3)157 (3)

Experimental details

Crystal data
Chemical formulaC15H16O2S
Mr260.34
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)7.2016 (14), 8.9375 (18), 10.922 (2)
α, β, γ (°)91.50 (3), 107.69 (3), 93.25 (3)
V (Å3)668.0 (2)
Z2
Radiation typeMo Kα
µ (mm−1)0.23
Crystal size (mm)0.10 × 0.10 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.977, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections		5891, 2705, 1958
Rint0.020
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.208, 1.15
No. of reflections2705
No. of parameters179
No. of restraints9
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.41, −0.45

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2D···O10.78 (3)1.89 (3)2.623 (3)157 (3)
 

Acknowledgements

This project was sponsored by the Cultivation Program of Young and Middle-aged Academic Leaders in Zhejiang Higher Education Institutions, the Natural Science Foundation of Ningbo City (Nos. 2009 A610047 and 2010 A610027) and the K. C. Wong Magna Fund of Ningbo University. We thank Professor X. Li for help with the structural analysis.

References

First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationQiu, L., Lin, J. & Xu, Y. (2009). Inorg. Chem. Commun. 12, 986–989.  Web of Science CSD CrossRef CAS Google Scholar
 First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, H., Zhang, D., Ni, Z.-H., Li, X., Tian, L. & Jiang, J. (2009). Inorg. Chem. 48, 5946–5956.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationWong, W.-K., Liang, H., Guo, J., Wong, W.-Y., Lo, W.-K., Li, K.-F., Cheah, K.-W., Zhou, Z. & Wong, W.-T. (2004). Eur. J. Inorg. Chem. 4, 829–836.  Web of Science CSD CrossRef Google Scholar
 First citationYu, T.-Z., Su, W.-M., Li, W.-L., Hong, Z.-R., Hua, R.-N. & Li, B. (2007). Thin Solid Films, 515, 4080–4084.  Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2218
https://doi.org/10.1107/S1600536810030382
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