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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 10| October 2010| Page o2667
doi:10.1107/S1600536810038328

N′-[(E)-1-(3,5-Di­chloro-2-hy­dr­oxy­phen­yl)ethyl­­idene]-4-meth­­oxy­benzo­hydrazide monohydrate

Chun-Hong He,a Jian-Ping Zhanga and Jian-Guo Changa*

aDepartment of Materials Science and chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
*Correspondence e-mail: tsucjg@163.com

(Received 21 September 2010; accepted 25 September 2010; online 30 September 2010)

The title compound, C16H14Cl2N2O3·H2O, displays a trans conformation with respect to the C=N double bond. The dihedral angle between the two benzene rings is 4.98 (12)°. Intra­molecular O—H⋯N and O—H⋯O hydrogen bonds occur. The crystal structure is stabilized by inter­molecular O—H⋯O and N—H⋯O hydrogen bonds. In addition, there are π–π inter­actions between the chemically distinct benzene rings of inversion-related mol­ecules [centroid–centroid separation = 3.715 (1) Å].

Related literature

For further details of the chemistry of the title compound, see: Carcelli et al. (1995[Carcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43-62.]); Salem (1998[Salem, A. A. (1998). Microchem. J. 60, 51-66.]). For a related stucture, see: Chang et al. (2007[Chang, J.-G. & Ji, C.-Y. (2007). Acta Cryst. E63, o3212.]).

[Scheme 1]

Experimental

Crystal data

  • C16H14Cl2N2O3·H2O

  • Mr = 371.21

  • Triclinic, [P \overline 1]

  • a = 7.033 (5) Å

  • b = 7.516 (7) Å

  • c = 16.647 (10) Å

  • α = 85.105 (10)°

  • β = 81.386 (12)°

  • γ = 79.414 (10)°

  • V = 853.7 (11) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.40 mm−1

  • T = 298 K

  • 0.30 × 0.23 × 0.16 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.906, Tmax = 0.946

  • 4423 measured reflections

  • 2936 independent reflections

  • 1997 reflections with I > 2σ(I)

  • Rint = 0.025
Refinement

  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.170

  • S = 1.00

  • 2936 reflections

  • 220 parameters

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O4 0.86 2.15 2.926 (5) 150
O1—H1⋯O2 0.82 2.58 3.287 (5) 146
O1—H1⋯N1 0.82 1.77 2.484 (5) 145
O4—H16⋯O1i 0.85 2.09 2.887 (5) 156
O4—H15⋯O2ii 0.85 1.88 2.726 (5) 176
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038328/pk2270sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810038328/pk2270Isup2.hkl

checkCIF report


Comment top

The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions and their biological activity (Carcelli et al., 1995; Salem, 1998; Chang et al., 2007). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound, was synthesized and its crystal structure is reported here.

The title molecule displays a trans conformation with respect to the C7=N1 double bond (Fig. 1). The dihedral angle between the two benzene rings is 4.98 (12) °. The crystal structure is stabilized by intramolecular O—H···N, O—H···O and intermolecular O—H···O, N—H···O hydrogen bonds. (Table. 1, Figs. 1 and 2). There are π - π interactions between the chemically distinct benzene rings on inversion related molecules [Cg···Cg = 3.715 (1) Å; Cg represents a ring centroid].

Related literature top

For further details of the chemistry of the title compound, see: Carcelli et al. (1995); Salem (1998). For a related stucture, see: Chang et al. (2007).

Experimental top

4-methoxybenzohydrazide (0.01 mol,1.66 g) was dissolved in anhydrous ethanol (50 ml), and 1-(3,5-dichloro-2-hydroxyphenyl)ethanone (0.01 mol, 2.05 g) was added. The reaction mixture was refluxed for 5 h with stirring, then the resulting precipitate was collected by filtration, washed several times with ethanol and dried in vacuo (yield 78%). The compound (1.0 mmol,0.35 g) was dissolved in dimethylformamide (30 ml) and kept at room temperature for 20d to obtain yellow single crystals suitable for X-ray diffraction.

Refinement top

All H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H (methyl) = 0.96 Å, C—H (aromatic) = 0.93 Å, O—H = 0.82 Å, N—H = 0.86 Å and with Uiso(H) = 1.5Ueq(Cmethyl, O and 1.2Ueq(Caromatic, Cmethylene, N).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30° probability level. Dashed lines show intramolecular O—H···N, O—H···O and intermolecular N—H···O hydrogen bonds.
[Figure 2] Fig. 2. Packing diagram of compound, Showing intermolecular O—H···O and N—H···O hydrogen bonds (dashed lines).
N'-[(E)-1-(3,5-Dichloro-2-hydroxyphenyl)ethylidene]-4- methoxybenzohydrazide monohydrate top
Crystal data top
C16H14Cl2N2O3·H2OZ = 2
Mr = 371.21F(000) = 384
Triclinic, P1Dx = 1.444 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.033 (5) ÅCell parameters from 1429 reflections
b = 7.516 (7) Åθ = 3.0–25.5°
c = 16.647 (10) ŵ = 0.40 mm−1
α = 85.105 (10)°T = 298 K
β = 81.386 (12)°Plate, yellow
γ = 79.414 (10)°0.30 × 0.23 × 0.16 mm
V = 853.7 (11) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2936 independent reflections
Radiation source: fine-focus sealed tube1997 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ϕ and ω scansθmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −8→8
Tmin = 0.906, Tmax = 0.946k = −6→8
4423 measured reflectionsl = −19→19
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0727P)2 + 0.8688P]
where P = (Fo2 + 2Fc2)/3
2936 reflections(Δ/σ)max < 0.001
220 parametersΔρmax = 0.56 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
Crystal data top
C16H14Cl2N2O3·H2Oγ = 79.414 (10)°
Mr = 371.21V = 853.7 (11) Å3
Triclinic, P1Z = 2
a = 7.033 (5) ÅMo Kα radiation
b = 7.516 (7) ŵ = 0.40 mm−1
c = 16.647 (10) ÅT = 298 K
α = 85.105 (10)°0.30 × 0.23 × 0.16 mm
β = 81.386 (12)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2936 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		1997 reflections with I > 2σ(I)
Tmin = 0.906, Tmax = 0.946Rint = 0.025
4423 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.170H-atom parameters constrained
S = 1.00Δρmax = 0.56 e Å−3
2936 reflectionsΔρmin = −0.32 e Å−3
220 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
Cl11.0655 (2)−0.37144 (18)0.19059 (9)0.0675 (5)
Cl20.8926 (3)0.3075 (2)0.05875 (8)0.0774 (6)
O10.9149 (5)−0.2090 (4)0.34325 (19)0.0462 (8)
H10.8675−0.15990.38560.069*
O20.7613 (6)−0.2102 (4)0.5397 (2)0.0611 (10)
O30.5111 (6)0.0452 (6)0.8985 (2)0.0714 (12)
O40.7853 (6)0.4252 (4)0.5716 (3)0.0710 (12)
N10.7805 (5)0.0497 (5)0.4303 (2)0.0367 (9)
N20.7259 (5)0.0879 (5)0.5112 (2)0.0392 (9)
H20.69830.19730.52640.047*
C10.8427 (6)0.1022 (6)0.2902 (3)0.0360 (9)
C20.9122 (6)−0.0844 (6)0.2809 (3)0.0374 (10)
C30.9789 (7)−0.1428 (6)0.2023 (3)0.0442 (11)
C40.9757 (7)−0.0251 (7)0.1341 (3)0.0488 (11)
H41.0221−0.06680.08260.059*
C50.9020 (7)0.1566 (7)0.1441 (3)0.0448 (11)
C60.8384 (7)0.2200 (6)0.2203 (3)0.0419 (10)
H60.79180.34320.22550.050*
C70.7781 (6)0.1720 (6)0.3720 (3)0.0357 (9)
C80.7186 (6)−0.0562 (6)0.5645 (3)0.0387 (10)
C90.6577 (6)−0.0211 (6)0.6511 (3)0.0387 (10)
C100.5662 (7)0.1480 (7)0.6775 (3)0.0452 (11)
H100.53930.24420.63960.054*
C110.5141 (7)0.1750 (7)0.7606 (3)0.0508 (12)
H110.45420.28870.77800.061*
C120.5526 (7)0.0310 (7)0.8165 (3)0.0483 (11)
C130.6383 (7)−0.1378 (7)0.7914 (3)0.0517 (12)
H130.6614−0.23460.82940.062*
C140.6904 (7)−0.1634 (7)0.7088 (3)0.0457 (11)
H140.7484−0.27800.69190.055*
C150.4310 (10)0.2206 (10)0.9292 (4)0.0819 (19)
H15A0.52020.30290.91090.123*
H15B0.41070.21030.98760.123*
H15C0.30860.26570.90950.123*
C160.7148 (6)0.3729 (4)0.3805 (3)0.0605 (15)
H16A0.68500.39690.43710.091*
H16B0.60080.41480.35420.091*
H16C0.81830.43510.35550.091*
H150.78390.53820.56110.14 (3)*
H160.89050.38840.59190.09 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0958 (12)0.0380 (7)0.0647 (9)−0.0048 (7)−0.0002 (8)−0.0142 (6)
Cl20.1369 (15)0.0568 (9)0.0331 (7)−0.0125 (9)−0.0067 (8)0.0091 (6)
O10.067 (2)0.0312 (17)0.0383 (18)−0.0054 (15)−0.0049 (16)0.0012 (14)
O20.104 (3)0.0296 (18)0.046 (2)−0.0090 (18)−0.0052 (19)0.0065 (15)
O30.089 (3)0.084 (3)0.034 (2)−0.001 (2)−0.0038 (19)0.0013 (19)
O40.090 (3)0.037 (2)0.096 (3)−0.0169 (19)−0.044 (3)0.007 (2)
N10.050 (2)0.031 (2)0.0279 (19)−0.0080 (16)−0.0040 (16)0.0009 (15)
N20.053 (2)0.0283 (19)0.035 (2)−0.0060 (16)−0.0037 (17)−0.0006 (16)
C10.038 (2)0.039 (2)0.032 (2)−0.0095 (18)−0.0057 (17)−0.0004 (17)
C20.041 (2)0.033 (2)0.038 (2)−0.0108 (18)−0.0052 (18)0.0006 (18)
C30.048 (2)0.041 (2)0.045 (2)−0.0085 (19)−0.005 (2)−0.007 (2)
C40.057 (3)0.049 (3)0.040 (2)−0.013 (2)−0.003 (2)−0.006 (2)
C50.058 (3)0.043 (2)0.034 (2)−0.013 (2)−0.007 (2)0.0028 (19)
C60.048 (2)0.038 (2)0.038 (2)−0.0076 (19)−0.0049 (19)0.0003 (19)
C70.043 (2)0.031 (2)0.033 (2)−0.0059 (17)−0.0058 (18)0.0025 (17)
C80.047 (2)0.029 (2)0.039 (2)−0.0067 (18)−0.0073 (19)0.0035 (18)
C90.040 (2)0.040 (2)0.037 (2)−0.0101 (18)−0.0062 (18)0.0037 (18)
C100.051 (3)0.043 (2)0.039 (2)−0.005 (2)−0.005 (2)0.002 (2)
C110.057 (3)0.047 (3)0.046 (3)−0.006 (2)−0.002 (2)−0.002 (2)
C120.048 (3)0.059 (3)0.037 (2)−0.008 (2)−0.005 (2)0.001 (2)
C130.051 (3)0.058 (3)0.043 (2)−0.006 (2)−0.008 (2)0.011 (2)
C140.050 (3)0.044 (2)0.041 (2)−0.006 (2)−0.005 (2)0.006 (2)
C150.100 (5)0.092 (5)0.048 (3)−0.004 (4)0.003 (3)−0.018 (3)
C160.098 (4)0.035 (3)0.041 (3)−0.001 (3)−0.001 (3)−0.001 (2)
Geometric parameters (Å, º) top
Cl1—C31.731 (5)C5—C61.376 (7)
Cl2—C51.742 (5)C6—H60.9300
O1—C21.338 (5)C7—C161.506 (5)
O1—H10.8200C8—C91.474 (6)
O2—C81.231 (5)C9—C141.385 (6)
O3—C121.362 (6)C9—C101.391 (6)
O3—C151.440 (7)C10—C111.399 (7)
O4—H150.8511C10—H100.9300
O4—H160.8496C11—C121.381 (7)
N1—C71.279 (5)C11—H110.9300
N1—N21.383 (5)C12—C131.372 (7)
N2—C81.344 (5)C13—C141.389 (7)
N2—H20.8600C13—H130.9300
C1—C61.401 (6)C14—H140.9300
C1—C21.412 (6)C15—H15A0.9600
C1—C71.477 (6)C15—H15B0.9600
C2—C31.401 (6)C15—H15C0.9600
C3—C41.378 (7)C16—H16A0.9600
C4—C51.383 (7)C16—H16B0.9600
C4—H40.9300C16—H16C0.9600
C2—O1—H1109.5C14—C9—C10118.5 (4)
C12—O3—C15118.7 (5)C14—C9—C8118.6 (4)
H15—O4—H16104.1C10—C9—C8122.9 (4)
C7—N1—N2123.2 (4)C9—C10—C11120.7 (5)
C8—N2—N1115.9 (4)C9—C10—H10119.7
C8—N2—H2122.0C11—C10—H10119.7
N1—N2—H2122.0C12—C11—C10119.3 (5)
C6—C1—C2118.5 (4)C12—C11—H11120.4
C6—C1—C7120.8 (4)C10—C11—H11120.4
C2—C1—C7120.7 (4)O3—C12—C13115.8 (5)
O1—C2—C3118.2 (4)O3—C12—C11123.4 (5)
O1—C2—C1123.3 (4)C13—C12—C11120.8 (5)
C3—C2—C1118.5 (4)C12—C13—C14119.6 (5)
C4—C3—C2122.3 (4)C12—C13—H13120.2
C4—C3—Cl1119.1 (4)C14—C13—H13120.2
C2—C3—Cl1118.6 (4)C9—C14—C13121.2 (5)
C3—C4—C5118.5 (4)C9—C14—H14119.4
C3—C4—H4120.8C13—C14—H14119.4
C5—C4—H4120.8O3—C15—H15A109.5
C6—C5—C4121.1 (4)O3—C15—H15B109.5
C6—C5—Cl2119.6 (4)H15A—C15—H15B109.5
C4—C5—Cl2119.3 (4)O3—C15—H15C109.5
C5—C6—C1121.1 (4)H15A—C15—H15C109.5
C5—C6—H6119.5H15B—C15—H15C109.5
C1—C6—H6119.5C7—C16—H16A109.5
N1—C7—C1114.5 (4)C7—C16—H16B109.5
N1—C7—C16125.9 (4)H16A—C16—H16B109.5
C1—C7—C16119.6 (4)C7—C16—H16C109.5
O2—C8—N2119.6 (4)H16A—C16—H16C109.5
O2—C8—C9122.8 (4)H16B—C16—H16C109.5
N2—C8—C9117.6 (4)
C7—N1—N2—C8173.8 (4)C6—C1—C7—C16−2.6 (6)
C6—C1—C2—O1−177.2 (4)C2—C1—C7—C16176.7 (4)
C7—C1—C2—O13.5 (6)N1—N2—C8—O20.7 (6)
C6—C1—C2—C31.7 (6)N1—N2—C8—C9−179.0 (4)
C7—C1—C2—C3−177.5 (4)O2—C8—C9—C1414.7 (7)
O1—C2—C3—C4177.9 (4)N2—C8—C9—C14−165.6 (4)
C1—C2—C3—C4−1.1 (7)O2—C8—C9—C10−164.4 (5)
O1—C2—C3—Cl1−1.4 (6)N2—C8—C9—C1015.3 (6)
C1—C2—C3—Cl1179.7 (3)C14—C9—C10—C112.0 (7)
C2—C3—C4—C5−0.7 (7)C8—C9—C10—C11−178.9 (4)
Cl1—C3—C4—C5178.5 (4)C9—C10—C11—C12−0.7 (7)
C3—C4—C5—C61.9 (7)C15—O3—C12—C13176.6 (5)
C3—C4—C5—Cl2−178.9 (4)C15—O3—C12—C11−2.9 (8)
C4—C5—C6—C1−1.3 (7)C10—C11—C12—O3178.5 (5)
Cl2—C5—C6—C1179.6 (4)C10—C11—C12—C13−1.0 (8)
C2—C1—C6—C5−0.6 (7)O3—C12—C13—C14−178.2 (4)
C7—C1—C6—C5178.7 (4)C11—C12—C13—C141.3 (8)
N2—N1—C7—C1179.8 (4)C10—C9—C14—C13−1.7 (7)
N2—N1—C7—C16−0.8 (7)C8—C9—C14—C13179.2 (4)
C6—C1—C7—N1176.9 (4)C12—C13—C14—C90.1 (7)
C2—C1—C7—N1−3.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O40.862.152.926 (5)150
O1—H1···O20.822.583.287 (5)146
O1—H1···N10.821.772.484 (5)145
O4—H16···O1i0.852.092.887 (5)156
O4—H15···O2ii0.851.882.726 (5)176
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC16H14Cl2N2O3·H2O
Mr371.21
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)7.033 (5), 7.516 (7), 16.647 (10)
α, β, γ (°)85.105 (10), 81.386 (12), 79.414 (10)
V (Å3)853.7 (11)
Z2
Radiation typeMo Kα
µ (mm−1)0.40
Crystal size (mm)0.30 × 0.23 × 0.16
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.906, 0.946
No. of measured, independent and
observed [I > 2σ(I)] reflections		4423, 2936, 1997
Rint0.025
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.170, 1.00
No. of reflections2936
No. of parameters220
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.56, −0.32

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O40.862.152.926 (5)150.1
O1—H1···O20.822.583.287 (5)145.5
O1—H1···N10.821.772.484 (5)145.1
O4—H16···O1i0.852.092.887 (5)155.9
O4—H15···O2ii0.851.882.726 (5)175.9
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y+1, z.
 

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (No. Y05–2–09)

References

First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCarcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43–62.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationChang, J.-G. & Ji, C.-Y. (2007). Acta Cryst. E63, o3212.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSalem, A. A. (1998). Microchem. J. 60, 51–66.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals 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.

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ISSN: 2056-9890
Volume 66| Part 10| October 2010| Page o2667
doi:10.1107/S1600536810038328
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