Hexaaqua­zinc(II) bis­[4-(2-hydroxy­benzyl­ideneamino)benzene­sulfonate]

Tai, X.-S.; Yin, J.; Hao, M.-Y.

doi:10.1107/S1600536807061703

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m273

doi:10.1107/S1600536807061703

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Hexaaquazinc(II) bis[4-(2-hydroxybenzylideneamino)benzenesulfonate]

Xi-Shi Tai,^a ^* Jie Yin ^b and Ming-Yang Hao ^c

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, ^bDepartment of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021, People's Republic of China, and ^cClinical College of Weifang Medical University, Weifang 261042, People's Republic of China
^*Correspondence e-mail: taixishi@lzu.edu.cn

(Received 7 May 2007; accepted 21 November 2007; online 4 January 2008)

In the title compound, [Zn(H₂O)₆](C₁₃H₁₀NO₄S)₂, a distorted ZnO₆ octahedron results from the coordination by the six water molecules. Only three of the water molecules are crystallographically unique, as the Zn atom lies on an inversion center. The Zn—O bond lengths are in the range 2.054 (4)–2.073 (4) Å. A network of hydrogen bonds helps to establish the crystal packing.

Related literature

For related literature, see: Tai et al. (2005 ).

Experimental

Crystal data

[Zn(H₂O)₆](C₁₃H₁₀NO₄S)₂
M_r = 726.03
Monoclinic, P 2₁ /n
a = 6.3255 (10) Å
b = 35.312 (3) Å
c = 6.9832 (10) Å
β = 90.391 (2)°
V = 1559.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.99 mm⁻¹
T = 298 (2) K
0.35 × 0.33 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.723, T_max = 0.826
6994 measured reflections
2708 independent reflections
2170 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.168
S = 1.08
2708 reflections
205 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7B⋯O3ⁱ	0.85	1.93	2.760 (6)	166
O7—H7A⋯O1	0.85	1.93	2.779 (5)	177
O6—H6B⋯O1ⁱⁱ	0.85	1.92	2.773 (6)	176
O6—H6A⋯O2ⁱⁱⁱ	0.85	1.92	2.770 (6)	175
O5—H5B⋯O3	0.85	1.90	2.745 (6)	171
O5—H5A⋯O2ⁱⁱ	0.85	1.91	2.742 (6)	167
O4—H4⋯N1	0.82	1.93	2.602 (7)	139
Symmetry codes: (i) x+1, y, z; (ii) x, y, z-1; (iii) x+1, y, z-1.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807061703/pr2013sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807061703/pr2013Isup2.hkl

checkCIF report

Comment top

As part of our onging studies of metal coordination complexes with Shiff base ligands (Tai et al., 2005), the synthesis and structure of the title compound, (I), is reported. Six water molecules are attached to the zinc atom, resulting in a distorted ZnO₆ octahedron (Fig. 1). The C7=N1 bond length [1.280 (9) Å] implies double bond character, while C4—O9 [1.332 (9) Å] is well regarded as a single bond. The dihedral angle between the two benzene ring mean planes (C1—C6 and C8—C13) is 32.2 (3)°. A network of hydrogen bonds helps to establish the crystal packing.

Related literature top

For related literature, see: Tai et al. (2005).

Experimental top

One mmol of zinc acetate was added to a solution of salicylaldehyde-4-aminobenzene sulfonic acid (1 mmol) in 20 ml of 95% CH₃CH₂OH. The mixture was continuously stirred for 2 h at refluxing temperature, evaporating some methanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 76%). Clear blocks of (I) were obtained by evaporation from a methanol solution after a week.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

Fig. 1. The complex molecule in (I) with 50% probabiility ellipsoids (arbitrary spheres for the H atoms).

Hexaaquazinc(II) bis[4-(2-hydroxybenzylideneamino)benzenesulfonate] top

Crystal data top

[Zn(H₂O)₆](C₁₃H₁₀NO4S)₂	F(000) = 752
M_r = 726.03	D_x = 1.546 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.3255 (10) Å	Cell parameters from 2287 reflections
b = 35.312 (3) Å	θ = 2.3–23.1°
c = 6.9832 (10) Å	µ = 0.99 mm⁻¹
β = 90.391 (2)°	T = 298 K
V = 1559.8 (4) Å³	Block, colourless
Z = 2	0.35 × 0.33 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2708 independent reflections
Radiation source: fine-focus sealed tube	2170 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
phi and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −7→5
T_min = 0.723, T_max = 0.826	k = −42→32
6994 measured reflections	l = −8→8

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.063P)² + 5.0428P] where P = (F_o² + 2F_c²)/3
2708 reflections	(Δ/σ)_max < 0.001
205 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.79 e Å⁻³

Crystal data top

[Zn(H₂O)₆](C₁₃H₁₀NO4S)₂	V = 1559.8 (4) Å³
M_r = 726.03	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.3255 (10) Å	µ = 0.99 mm⁻¹
b = 35.312 (3) Å	T = 298 K
c = 6.9832 (10) Å	0.35 × 0.33 × 0.20 mm
β = 90.391 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2708 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2170 reflections with I > 2σ(I)
T_min = 0.723, T_max = 0.826	R_int = 0.034
6994 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.08	Δρ_max = 0.37 e Å⁻³
2708 reflections	Δρ_min = −0.79 e Å⁻³
205 parameters

Special details top

Experimental. 'SADABS v2.0 (Bruker, 1997)'

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

	x	y	z	U_iso*/U_eq
Zn1	1.0000	0.0000	0.0000	0.0366 (3)
N1	0.4209 (9)	0.23101 (16)	0.5074 (8)	0.0590 (15)
O1	0.8397 (6)	0.06182 (11)	0.5063 (6)	0.0432 (10)
O2	0.5147 (6)	0.05114 (12)	0.6744 (6)	0.0517 (11)
O3	0.5147 (6)	0.05133 (12)	0.3282 (6)	0.0508 (11)
O4	0.1459 (9)	0.28426 (15)	0.5713 (9)	0.0841 (17)
H4	0.1765	0.2635	0.5271	0.126*
O5	0.7091 (6)	0.02586 (12)	0.0024 (6)	0.0508 (11)
H5A	0.6633	0.0365	−0.0989	0.061*
H5B	0.6403	0.0352	0.0953	0.061*
O6	1.1063 (6)	0.03918 (14)	−0.1984 (7)	0.0634 (13)
H6A	1.2325	0.0438	−0.2321	0.076*
H6B	1.0273	0.0452	−0.2926	0.076*
O7	1.1046 (6)	0.03394 (15)	0.2234 (6)	0.0659 (14)
H7A	1.0205	0.0428	0.3067	0.079*
H7B	1.2285	0.0364	0.2696	0.079*
S1	0.6114 (2)	0.06635 (4)	0.5026 (2)	0.0358 (4)
C1	0.5612 (8)	0.11535 (16)	0.4999 (7)	0.0352 (12)
C2	0.7196 (10)	0.14097 (18)	0.5569 (9)	0.0504 (16)
H2	0.8529	0.1323	0.5932	0.060*
C3	0.6734 (12)	0.17949 (19)	0.5582 (10)	0.0616 (19)
H3	0.7770	0.1968	0.5946	0.074*
C4	0.4756 (11)	0.19220 (18)	0.5058 (10)	0.0534 (16)
C5	0.3215 (11)	0.16672 (18)	0.4537 (10)	0.0577 (18)
H5	0.1871	0.1755	0.4217	0.069*
C6	0.3630 (9)	0.12829 (17)	0.4482 (9)	0.0486 (15)
H6	0.2584	0.1113	0.4100	0.058*
C7	0.5591 (11)	0.25692 (19)	0.4805 (9)	0.0551 (17)
H7	0.6977	0.2500	0.4540	0.066*
C8	0.5058 (12)	0.29691 (18)	0.4902 (10)	0.0567 (17)
C9	0.3022 (13)	0.3086 (2)	0.5377 (11)	0.067 (2)
C10	0.2618 (15)	0.3473 (2)	0.5562 (11)	0.072 (2)
H10	0.1281	0.3554	0.5926	0.086*
C11	0.4158 (15)	0.3734 (2)	0.5214 (11)	0.073 (2)
H11	0.3849	0.3991	0.5311	0.087*
C12	0.6194 (16)	0.3620 (2)	0.4714 (12)	0.082 (2)
H12	0.7243	0.3798	0.4477	0.098*
C13	0.6621 (13)	0.3239 (2)	0.4578 (11)	0.067 (2)
H13	0.7978	0.3160	0.4264	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0234 (4)	0.0495 (6)	0.0370 (5)	−0.0006 (4)	−0.0002 (3)	−0.0018 (4)
N1	0.064 (4)	0.047 (3)	0.066 (4)	0.013 (3)	−0.002 (3)	−0.007 (3)
O1	0.0223 (18)	0.062 (3)	0.046 (2)	0.0040 (17)	0.0003 (16)	0.003 (2)
O2	0.037 (2)	0.066 (3)	0.052 (3)	0.003 (2)	0.0060 (19)	0.018 (2)
O3	0.032 (2)	0.064 (3)	0.057 (3)	0.0026 (19)	−0.0060 (19)	−0.011 (2)
O4	0.085 (4)	0.068 (3)	0.100 (5)	0.013 (3)	0.027 (3)	0.005 (3)
O5	0.035 (2)	0.079 (3)	0.038 (2)	0.016 (2)	0.0023 (18)	0.002 (2)
O6	0.031 (2)	0.099 (4)	0.060 (3)	−0.005 (2)	−0.003 (2)	0.030 (3)
O7	0.029 (2)	0.109 (4)	0.060 (3)	−0.002 (2)	−0.004 (2)	−0.038 (3)
S1	0.0239 (7)	0.0472 (8)	0.0362 (7)	0.0032 (6)	0.0008 (5)	−0.0001 (6)
C1	0.028 (3)	0.047 (3)	0.031 (3)	0.005 (2)	−0.001 (2)	−0.005 (2)
C2	0.039 (3)	0.060 (4)	0.053 (4)	−0.005 (3)	−0.010 (3)	0.000 (3)
C3	0.066 (5)	0.049 (4)	0.069 (5)	−0.007 (3)	−0.007 (4)	−0.012 (3)
C4	0.053 (4)	0.051 (4)	0.056 (4)	0.012 (3)	0.010 (3)	−0.002 (3)
C5	0.046 (4)	0.048 (4)	0.079 (5)	0.007 (3)	−0.007 (3)	0.000 (3)
C6	0.037 (3)	0.047 (4)	0.062 (4)	0.005 (3)	−0.014 (3)	0.001 (3)
C7	0.058 (4)	0.055 (4)	0.053 (4)	0.008 (3)	0.001 (3)	−0.005 (3)
C8	0.068 (4)	0.048 (4)	0.053 (4)	0.003 (4)	−0.002 (3)	−0.014 (3)
C9	0.081 (6)	0.061 (5)	0.058 (5)	0.006 (4)	0.006 (4)	−0.001 (4)
C10	0.104 (7)	0.052 (4)	0.059 (5)	0.019 (4)	0.005 (4)	−0.003 (3)
C11	0.108 (7)	0.047 (4)	0.062 (5)	0.019 (4)	−0.006 (4)	−0.002 (4)
C12	0.109 (8)	0.052 (5)	0.084 (6)	0.002 (5)	−0.007 (5)	0.003 (4)
C13	0.073 (5)	0.059 (5)	0.071 (5)	0.002 (4)	−0.008 (4)	−0.007 (4)

Geometric parameters (Å, º) top

Zn1—O5ⁱ	2.054 (4)	C1—C2	1.406 (8)
Zn1—O5	2.054 (4)	C2—C3	1.391 (9)
Zn1—O7ⁱ	2.072 (4)	C2—H2	0.9300
Zn1—O7	2.072 (4)	C3—C4	1.376 (9)
Zn1—O6	2.073 (4)	C3—H3	0.9300
Zn1—O6ⁱ	2.073 (4)	C4—C5	1.374 (9)
N1—C7	1.280 (9)	C5—C6	1.383 (9)
N1—C4	1.413 (8)	C5—H5	0.9300
O1—S1	1.453 (4)	C6—H6	0.9300
O2—S1	1.453 (4)	C7—C8	1.454 (9)
O3—S1	1.459 (4)	C7—H7	0.9300
O4—C9	1.332 (9)	C8—C13	1.394 (10)
O4—H4	0.8200	C8—C9	1.394 (10)
O5—H5A	0.8500	C9—C10	1.397 (10)
O5—H5B	0.8499	C10—C11	1.365 (11)
O6—H6A	0.8500	C10—H10	0.9300
O6—H6B	0.8500	C11—C12	1.396 (12)
O7—H7A	0.8500	C11—H11	0.9300
O7—H7B	0.8500	C12—C13	1.375 (10)
S1—C1	1.759 (6)	C12—H12	0.9300
C1—C6	1.380 (8)	C13—H13	0.9300

O5ⁱ—Zn1—O5	180.0 (2)	C3—C2—H2	120.6
O5ⁱ—Zn1—O7ⁱ	91.04 (17)	C1—C2—H2	120.6
O5—Zn1—O7ⁱ	88.96 (17)	C4—C3—C2	120.5 (6)
O5ⁱ—Zn1—O7	88.96 (17)	C4—C3—H3	119.7
O5—Zn1—O7	91.04 (17)	C2—C3—H3	119.7
O7ⁱ—Zn1—O7	180.0 (3)	C5—C4—C3	119.9 (6)
O5ⁱ—Zn1—O6	89.80 (17)	C5—C4—N1	117.6 (6)
O5—Zn1—O6	90.20 (17)	C3—C4—N1	122.4 (6)
O7ⁱ—Zn1—O6	89.2 (2)	C4—C5—C6	121.0 (6)
O7—Zn1—O6	90.8 (2)	C4—C5—H5	119.5
O5ⁱ—Zn1—O6ⁱ	90.20 (17)	C6—C5—H5	119.5
O5—Zn1—O6ⁱ	89.80 (17)	C1—C6—C5	119.4 (6)
O7ⁱ—Zn1—O6ⁱ	90.8 (2)	C1—C6—H6	120.3
O7—Zn1—O6ⁱ	89.2 (2)	C5—C6—H6	120.3
O6—Zn1—O6ⁱ	180.0 (3)	N1—C7—C8	121.9 (7)
C7—N1—C4	121.6 (6)	N1—C7—H7	119.1
C9—O4—H4	109.5	C8—C7—H7	119.1
Zn1—O5—H5A	119.3	C13—C8—C9	119.6 (7)
Zn1—O5—H5B	129.9	C13—C8—C7	119.5 (7)
H5A—O5—H5B	106.9	C9—C8—C7	120.9 (7)
Zn1—O6—H6A	128.5	O4—C9—C8	122.6 (7)
Zn1—O6—H6B	119.5	O4—C9—C10	118.6 (8)
H6A—O6—H6B	106.6	C8—C9—C10	118.8 (8)
Zn1—O7—H7A	122.0	C11—C10—C9	120.9 (8)
Zn1—O7—H7B	129.4	C11—C10—H10	119.5
H7A—O7—H7B	106.4	C9—C10—H10	119.5
O1—S1—O2	111.6 (2)	C10—C11—C12	120.6 (7)
O1—S1—O3	112.7 (2)	C10—C11—H11	119.7
O2—S1—O3	112.2 (3)	C12—C11—H11	119.7
O1—S1—C1	106.7 (2)	C13—C12—C11	118.8 (8)
O2—S1—C1	107.2 (3)	C13—C12—H12	120.6
O3—S1—C1	105.9 (2)	C11—C12—H12	120.6
C6—C1—C2	120.4 (5)	C12—C13—C8	121.2 (8)
C6—C1—S1	119.5 (4)	C12—C13—H13	119.4
C2—C1—S1	120.1 (4)	C8—C13—H13	119.4
C3—C2—C1	118.8 (6)

O1—S1—C1—C6	163.8 (5)	S1—C1—C6—C5	177.4 (5)
O2—S1—C1—C6	−76.5 (5)	C4—C5—C6—C1	1.4 (10)
O3—S1—C1—C6	43.5 (5)	C4—N1—C7—C8	−177.3 (6)
O1—S1—C1—C2	−18.6 (5)	N1—C7—C8—C13	−179.4 (7)
O2—S1—C1—C2	101.1 (5)	N1—C7—C8—C9	2.8 (11)
O3—S1—C1—C2	−138.9 (5)	C13—C8—C9—O4	−179.7 (7)
C6—C1—C2—C3	−0.7 (9)	C7—C8—C9—O4	−1.9 (11)
S1—C1—C2—C3	−178.3 (5)	C13—C8—C9—C10	−1.5 (11)
C1—C2—C3—C4	0.5 (10)	C7—C8—C9—C10	176.3 (7)
C2—C3—C4—C5	0.7 (11)	O4—C9—C10—C11	−179.3 (7)
C2—C3—C4—N1	179.1 (6)	C8—C9—C10—C11	2.5 (12)
C7—N1—C4—C5	−152.7 (7)	C9—C10—C11—C12	−1.7 (12)
C7—N1—C4—C3	28.8 (10)	C10—C11—C12—C13	0.0 (12)
C3—C4—C5—C6	−1.7 (11)	C11—C12—C13—C8	0.9 (12)
N1—C4—C5—C6	179.8 (6)	C9—C8—C13—C12	−0.1 (11)
C2—C1—C6—C5	−0.2 (9)	C7—C8—C13—C12	−178.0 (7)

Symmetry code: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O3ⁱⁱ	0.85	1.93	2.760 (6)	166
O7—H7A···O1	0.85	1.93	2.779 (5)	177
O6—H6B···O1ⁱⁱⁱ	0.85	1.92	2.773 (6)	176
O6—H6A···O2^iv	0.85	1.92	2.770 (6)	175
O5—H5B···O3	0.85	1.90	2.745 (6)	171
O5—H5A···O2ⁱⁱⁱ	0.85	1.91	2.742 (6)	167
O4—H4···N1	0.82	1.93	2.602 (7)	139

Symmetry codes: (ii) x+1, y, z; (iii) x, y, z−1; (iv) x+1, y, z−1.

Experimental details

Crystal data
Chemical formula	[Zn(H₂O)₆](C₁₃H₁₀NO4S)₂
M_r	726.03
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	6.3255 (10), 35.312 (3), 6.9832 (10)
β (°)	90.391 (2)
V (Å³)	1559.8 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.35 × 0.33 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.723, 0.826
No. of measured, independent and observed [I > 2σ(I)] reflections	6994, 2708, 2170
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.168, 1.08
No. of reflections	2708
No. of parameters	205
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.79

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O3ⁱ	0.85	1.93	2.760 (6)	166.3
O7—H7A···O1	0.85	1.93	2.779 (5)	177.0
O6—H6B···O1ⁱⁱ	0.85	1.92	2.773 (6)	175.6
O6—H6A···O2ⁱⁱⁱ	0.85	1.92	2.770 (6)	175.2
O5—H5B···O3	0.85	1.90	2.745 (6)	171.0
O5—H5A···O2ⁱⁱ	0.85	1.91	2.742 (6)	167.0
O4—H4···N1	0.82	1.93	2.602 (7)	138.6

Symmetry codes: (i) x+1, y, z; (ii) x, y, z−1; (iii) x+1, y, z−1.

Acknowledgements

The authors thank the National Natural Science Foundation of China (20671073), NingXia Natural Gas Transferring Key Laboratory (2004007), the Science and Technology Foundation of Weifang and Weifang University for research grants.

References

Bruker (1997). SMART (Version 5.044), SAINT (Version 5.01), SADABS (Version 2.0) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Tai, X. S., Liu, W. Y., Liu, Y. Z. & Li, Y. Z. (2005). Acta Cryst. E61, o389–o390. Web of Science CSD CrossRef IUCr Journals Google Scholar