catena-Poly[[tetra­aqua­[trans-1,2-bis­(4-pyrid­yl)ethene-κ2N:N′]nickel(II)] dinitrate]

Hyun, M.Y.; Kim, P.-G.; Kim, C.; Kim, Y.

doi:10.1107/S1600536811007021

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page m390

doi:10.1107/S1600536811007021

Open

access

catena-Poly[[tetraaqua[trans-1,2-bis(4-pyridyl)ethene-κ²N:N′]nickel(II)] dinitrate]

Min Young Hyun,^a Pan-Gi Kim,^b Cheal Kim ^a ^* and Youngmee Kim ^c ^*

^aDepartment of Fine Chemistry, Seoul National University of Science and Technology, Seoul 139-743, Republic of Korea, ^bDepartment of Forest & Environment Resources, Kyungpook National University, Sangju 742-711, Republic of Korea, and ^cDepartment of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Republic of Korea
^*Correspondence e-mail: chealkim@soultech.ac.kr, ymeekim@ewha.ac.kr

(Received 10 February 2011; accepted 24 February 2011; online 2 March 2011)

In the title compound, {[Ni(C₁₂H₁₀N₂)(H₂O)₄](NO₃)₂}_n, the Ni^II ion, lying on a crystallographic inversion center, has a distorted octahedral coordination sphere comprising four water ligands and two N-atom donors from the trans-related 1,2-bis(4-pyridyl)ethene ligands, which also have crystallographic inversion symmetry. These ligands bridge the Ni^II complex units, forming chains extending along the [110] and [ $[\overline1]$ 10] directions. The nitrate counter-anions stabilize the crystal structure through water–nitrate O—H⋯O hydrogen bonds.

Related literature

For interactions of metal ions with amino acids, see: Daniele et al. (2008 ); Parkin (2004 ); Tshuva & Lippard (2004 ). For related complexes,see: Lee et al. (2008 ); Yu et al. (2008 ); Park et al. (2008 ); Shin et al. (2009 ); Yu et al. (2009 , 2010 ); Kim et al. (2011 ).

Experimental

Crystal data

[Ni(C₁₂H₁₀N₂)(H₂O)₄](NO₃)₂
M_r = 436.99
Monoclinic, P 2₁ /n
a = 7.415 (3) Å
b = 11.426 (4) Å
c = 10.950 (4) Å
β = 97.307 (7)°
V = 920.1 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.11 mm⁻¹
T = 293 K
0.15 × 0.08 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
4954 measured reflections
1799 independent reflections
1116 reflections with I > 2σ(I)
R_int = 0.173

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.238
S = 1.14
1799 reflections
136 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.08 e Å⁻³
Δρ_min = −1.86 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O3ⁱ	0.93 (7)	2.28 (8)	3.176 (9)	162 (8)
O2—H2A⋯O5ⁱⁱ	0.93 (6)	2.14 (7)	3.068 (8)	176 (7)
O1—H1B⋯O3ⁱⁱⁱ	0.93 (4)	2.29 (2)	3.212 (9)	170 (8)
O1—H1A⋯O4^iv	0.93 (6)	2.37 (3)	3.252 (8)	158 (7)
Symmetry codes: (i) x, y, z-1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+2, -z+1; (iv) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811007021/zs2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007021/zs2096Isup2.hkl

checkCIF report

Comment top

The interaction of transition metal ions with biologically active molecules such as amino acids and various acids is very important in biological systems (Daniele et al., 2008; Parkin, 2004; Tshuva & Lippard, 2004). In attempting to model the interaction, we have extensively studied the interaction of the transition metal carboxylates e.g. copper(II), cadmium(II), and zinc(II) benzoates with a variety of spacers such as quinoxaline, 6-methylquinoline, 3-methylquinoline, trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene, and di-2-pyridyl ketone (Lee et al., 2008; Yu et al., 2008; Park et al., 2008; Shin et al., 2009; Yu et al., 2009; Yu et al., 2010; Kim et al., 2011). However, nickel as a metal ion source has rarely been used. In this work, we have employed nickel(II) trimethylacetate as a building block and trans-1,2-bis(4-pyridyl)ethene as a ligand. We report here on the structure of a new complex poly[tetraqua[trans-1,2-bis(4-pyridyl)ethene]nickel(II) dinitrate].

In the crystal structure of the title compound, [Ni(C₁₂H₁₀N₂)(H₂O)₄] . 2(NO₃)]_n, the Ni^II ion lies on a crystallographic inversion center with the distorted octahedral coordination sphere comprising four water ligands and two N donors from the trans-related 1,2-bis(4-pyridyl)ethene ligands, which also have crystallographic inversion symmetry (Fig. 1). These ligands bridge the Ni^II complex units to form a one-dimensional chain structure. The nitrate counter-anions stabilize the crystal structure through water O—H···O_nitrate hydrogen bonds (Table 1).

Related literature top

For interactions of metal ions with amino acids, see: Daniele et al. (2008); Parkin (2004); Tshuva & Lippard (2004). For related complexes,see: Lee et al. (2008); Yu et al. (2008); Park et al. (2008); Shin et al. (2009); Yu et al. (2009, 2010); Kim et al. (2011).

Experimental top

36.4 mg (0.125 mmol) of Ni(NO₃)₂^.6H₂O and 29.0 mg (0.25 mmol) of (CH₃)₃CCOOH and 29.5 mg (0. 25 mmol) of NH₄OH were dissolved in 4 ml of methanol and carefully layered with 4 ml of a chloroform solution of trans-1,2-bis(4-pyridyl)ethene (47.0 mg, 0.25 mmol). Crystals of the title compound suitable for X-ray analysis were obtained within a month.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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

Fig. 1. A fragment of one-dimensional chain structure of the title compound showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Inter-species hydrogen bonds are shown as dashed lines. For symmetry codes: (i) (-x + 1, -y + 1, -z); (ii) -x, -y + 2, -z). For other codes, see Table 1.

catena-Poly[[tetraaqua[trans-1,2-bis(4-pyridyl)ethene- κ²N:N']nickel(II)] dinitrate] top

Crystal data top

[Ni(C₁₂H₁₀N₂)(H₂O)₄](NO₃)₂	F(000) = 452
M_r = 436.99	D_x = 1.577 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1268 reflections
a = 7.415 (3) Å	θ = 2.6–23.4°
b = 11.426 (4) Å	µ = 1.11 mm⁻¹
c = 10.950 (4) Å	T = 293 K
β = 97.307 (7)°	Block, brown
V = 920.1 (6) Å³	0.15 × 0.08 × 0.08 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1116 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.173
Graphite monochromator	θ_max = 26.0°, θ_min = 2.6°
ϕ and ω scans	h = −8→9
4954 measured reflections	k = −11→14
1799 independent reflections	l = −11→13

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.238	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.1257P)²] where P = (F_o² + 2F_c²)/3
1799 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 1.08 e Å⁻³
4 restraints	Δρ_min = −1.86 e Å⁻³

Crystal data top

[Ni(C₁₂H₁₀N₂)(H₂O)₄](NO₃)₂	V = 920.1 (6) Å³
M_r = 436.99	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.415 (3) Å	µ = 1.11 mm⁻¹
b = 11.426 (4) Å	T = 293 K
c = 10.950 (4) Å	0.15 × 0.08 × 0.08 mm
β = 97.307 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1116 reflections with I > 2σ(I)
4954 measured reflections	R_int = 0.173
1799 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	4 restraints
wR(F²) = 0.238	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 1.08 e Å⁻³
1799 reflections	Δρ_min = −1.86 e Å⁻³
136 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

	x	y	z	U_iso*/U_eq
C1	0.0496 (8)	0.7389 (5)	−0.0578 (7)	0.0346 (15)
H1	−0.0705	0.7450	−0.0939	0.042*
C2	0.1365 (8)	0.6328 (5)	−0.0637 (7)	0.0414 (18)
H2	0.0758	0.5697	−0.1038	0.050*
C3	0.3181 (8)	0.6207 (5)	−0.0086 (7)	0.0364 (16)
C4	0.3954 (8)	0.7169 (5)	0.0524 (7)	0.0374 (16)
H4	0.5137	0.7129	0.0923	0.045*
C5	0.2991 (7)	0.8183 (5)	0.0544 (7)	0.0350 (16)
H5	0.3542	0.8814	0.0981	0.042*
C6	0.4117 (9)	0.5087 (5)	−0.0174 (8)	0.0431 (19)
H6	0.3429	0.4452	−0.0495	0.052*
N1	0.1284 (6)	0.8326 (4)	−0.0032 (5)	0.0271 (11)
Ni1	0.0000	1.0000	0.0000	0.0287 (4)
O1	0.0809 (9)	1.0135 (4)	0.1951 (7)	0.0630 (17)
H1A	0.098 (12)	0.946 (4)	0.242 (7)	0.076*
H1B	0.200 (4)	1.036 (7)	0.189 (9)	0.076*
O2	0.2381 (6)	1.0811 (4)	−0.0466 (7)	0.0666 (18)
H2A	0.226 (11)	1.148 (5)	−0.095 (7)	0.080*
H2B	0.306 (10)	1.024 (6)	−0.080 (9)	0.080*
N2	0.4686 (7)	0.8286 (5)	0.7660 (6)	0.0481 (16)
O3	0.4935 (7)	0.9318 (4)	0.8009 (6)	0.0684 (17)
O4	0.5938 (8)	0.7571 (5)	0.7875 (7)	0.0699 (18)
O5	0.3209 (7)	0.7990 (5)	0.7106 (7)	0.083 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.031 (3)	0.026 (3)	0.046 (4)	0.005 (2)	0.000 (3)	−0.002 (3)
C2	0.030 (3)	0.023 (3)	0.069 (5)	0.003 (2)	−0.005 (3)	−0.010 (3)
C3	0.030 (3)	0.018 (3)	0.060 (5)	0.009 (2)	−0.001 (3)	0.004 (3)
C4	0.028 (3)	0.018 (3)	0.064 (5)	0.004 (2)	−0.005 (3)	0.000 (3)
C5	0.024 (3)	0.020 (3)	0.060 (5)	0.001 (2)	0.001 (3)	−0.001 (3)
C6	0.037 (3)	0.014 (3)	0.076 (6)	0.009 (2)	0.000 (3)	−0.003 (3)
N1	0.027 (2)	0.022 (2)	0.033 (3)	0.0061 (19)	0.005 (2)	−0.001 (2)
Ni1	0.0214 (6)	0.0136 (6)	0.0485 (8)	0.0038 (4)	−0.0049 (5)	−0.0014 (4)
O1	0.066 (4)	0.051 (3)	0.066 (4)	0.000 (3)	−0.013 (3)	0.000 (3)
O2	0.044 (3)	0.035 (3)	0.121 (6)	0.003 (2)	0.010 (3)	0.012 (3)
N2	0.040 (3)	0.036 (3)	0.064 (5)	−0.003 (2)	−0.012 (3)	−0.010 (3)
O3	0.064 (3)	0.035 (3)	0.098 (5)	−0.008 (2)	−0.018 (3)	−0.016 (3)
O4	0.059 (3)	0.059 (3)	0.091 (5)	0.017 (3)	0.006 (3)	−0.008 (3)
O5	0.055 (3)	0.074 (4)	0.110 (6)	−0.017 (3)	−0.030 (4)	−0.016 (4)

Geometric parameters (Å, º) top

C1—N1	1.326 (7)	N1—Ni1	2.138 (4)
C1—C2	1.378 (8)	Ni1—O2	2.113 (5)
C1—H1	0.9300	Ni1—O2ⁱⁱ	2.113 (5)
C2—C3	1.411 (8)	Ni1—N1ⁱⁱ	2.138 (4)
C2—H2	0.9300	Ni1—O1ⁱⁱ	2.149 (7)
C3—C4	1.373 (8)	Ni1—O1	2.149 (7)
C3—C6	1.465 (8)	O1—H1A	0.93 (6)
C4—C5	1.362 (7)	O1—H1B	0.93 (4)
C4—H4	0.9300	O2—H2A	0.93 (6)
C5—N1	1.350 (7)	O2—H2B	0.93 (7)
C5—H5	0.9300	N2—O5	1.231 (6)
C6—C6ⁱ	1.331 (13)	N2—O4	1.236 (7)
C6—H6	0.9300	N2—O3	1.245 (7)

N1—C1—C2	123.4 (5)	O2ⁱⁱ—Ni1—N1ⁱⁱ	90.05 (18)
N1—C1—H1	118.3	O2—Ni1—N1	90.05 (18)
C2—C1—H1	118.3	O2ⁱⁱ—Ni1—N1	89.95 (18)
C1—C2—C3	119.5 (5)	N1ⁱⁱ—Ni1—N1	180.0
C1—C2—H2	120.3	O2—Ni1—O1ⁱⁱ	85.9 (3)
C3—C2—H2	120.3	O2ⁱⁱ—Ni1—O1ⁱⁱ	94.1 (3)
C4—C3—C2	116.5 (5)	N1ⁱⁱ—Ni1—O1ⁱⁱ	90.7 (2)
C4—C3—C6	124.0 (5)	N1—Ni1—O1ⁱⁱ	89.3 (2)
C2—C3—C6	119.5 (5)	O2—Ni1—O1	94.1 (3)
C5—C4—C3	120.1 (5)	O2ⁱⁱ—Ni1—O1	85.9 (3)
C5—C4—H4	119.9	N1ⁱⁱ—Ni1—O1	89.3 (2)
C3—C4—H4	119.9	N1—Ni1—O1	90.7 (2)
N1—C5—C4	123.9 (6)	O1ⁱⁱ—Ni1—O1	179.999 (2)
N1—C5—H5	118.1	Ni1—O1—H1A	119 (6)
C4—C5—H5	118.1	Ni1—O1—H1B	96 (6)
C6ⁱ—C6—C3	124.7 (7)	H1A—O1—H1B	102 (8)
C6ⁱ—C6—H6	117.7	Ni1—O2—H2A	118 (5)
C3—C6—H6	117.7	Ni1—O2—H2B	108 (5)
C1—N1—C5	116.5 (5)	H2A—O2—H2B	112 (9)
C1—N1—Ni1	123.9 (4)	O5—N2—O4	120.8 (6)
C5—N1—Ni1	119.6 (4)	O5—N2—O3	120.0 (6)
O2—Ni1—O2ⁱⁱ	180.0	O4—N2—O3	119.3 (5)
O2—Ni1—N1ⁱⁱ	89.95 (18)

N1—C1—C2—C3	0.7 (12)	C4—C5—N1—C1	4.3 (10)
C1—C2—C3—C4	2.2 (11)	C4—C5—N1—Ni1	−176.6 (6)
C1—C2—C3—C6	−178.6 (7)	C1—N1—Ni1—O2	−134.3 (5)
C2—C3—C4—C5	−1.8 (11)	C5—N1—Ni1—O2	46.7 (5)
C6—C3—C4—C5	179.1 (7)	C1—N1—Ni1—O2ⁱⁱ	45.7 (5)
C3—C4—C5—N1	−1.5 (11)	C5—N1—Ni1—O2ⁱⁱ	−133.3 (5)
C4—C3—C6—C6ⁱ	−9.6 (17)	C1—N1—Ni1—O1ⁱⁱ	−48.4 (5)
C2—C3—C6—C6ⁱ	171.3 (11)	C5—N1—Ni1—O1ⁱⁱ	132.5 (5)
C2—C1—N1—C5	−3.8 (10)	C1—N1—Ni1—O1	131.6 (5)
C2—C1—N1—Ni1	177.1 (6)	C5—N1—Ni1—O1	−47.5 (5)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O3ⁱⁱⁱ	0.93 (7)	2.28 (8)	3.176 (9)	162 (8)
O2—H2A···O5^iv	0.93 (6)	2.14 (7)	3.068 (8)	176 (7)
O1—H1B···O3^v	0.93 (4)	2.29 (2)	3.212 (9)	170 (8)
O1—H1A···O4^vi	0.93 (6)	2.37 (3)	3.252 (8)	158 (7)

Symmetry codes: (iii) x, y, z−1; (iv) −x+1/2, y+1/2, −z+1/2; (v) −x+1, −y+2, −z+1; (vi) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₂H₁₀N₂)(H₂O)₄](NO₃)₂
M_r	436.99
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.415 (3), 11.426 (4), 10.950 (4)
β (°)	97.307 (7)
V (Å³)	920.1 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.11
Crystal size (mm)	0.15 × 0.08 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4954, 1799, 1116
R_int	0.173
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.238, 1.14
No. of reflections	1799
No. of parameters	136
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.08, −1.86

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O3ⁱ	0.93 (7)	2.28 (8)	3.176 (9)	162 (8)
O2—H2A···O5ⁱⁱ	0.93 (6)	2.14 (7)	3.068 (8)	176 (7)
O1—H1B···O3ⁱⁱⁱ	0.93 (4)	2.291 (18)	3.212 (9)	170 (8)
O1—H1A···O4^iv	0.93 (6)	2.37 (3)	3.252 (8)	158 (7)

Symmetry codes: (i) x, y, z−1; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z+1; (iv) x−1/2, −y+3/2, z−1/2.

Acknowledgements

Financial support from the Forest Science & Technology Projects (S121010L080120) and the Cooperative Research Program for Agricultural Science & Technology Development (20070301–036-019–02) is gratefully acknowledged.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Daniele, P. G., Foti, C., Gianguzza, A., Prenesti, E. & Sammartano, S. (2008). Coord. Chem. Rev. 252, 1093–1107. Web of Science CrossRef CAS Google Scholar
Kim, J. H., Kim, C. & Kim, Y. (2011). Acta Cryst. E67, m3–m4. Web of Science CrossRef IUCr Journals Google Scholar
Lee, E. Y., Park, B. K., Kim, C., Kim, S.-J. & Kim, Y. (2008). Acta Cryst. E64, m286. Web of Science CSD CrossRef IUCr Journals Google Scholar
Park, B. K., Jang, K.-H., Kim, P.-G., Kim, C. & Kim, Y. (2008). Acta Cryst. E64, m1141. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parkin, G. (2004). Chem. Rev. 104, 699–767. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shin, D. H., Han, S.-H., Kim, P.-G., Kim, C. & Kim, Y. (2009). Acta Cryst. E65, m658–m659. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tshuva, E. Y. & Lippard, S. J. (2004). Chem. Rev. 104, 987–1012. Web of Science CrossRef PubMed CAS Google Scholar
Yu, S. M., Koo, K., Kim, P.-G., Kim, C. & Kim, Y. (2010). Acta Cryst. E66, m61–m62. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yu, S. M., Park, C.-H., Kim, P.-G., Kim, C. & Kim, Y. (2008). Acta Cryst. E64, m881–m882. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yu, S. M., Shin, D. H., Kim, P.-G., Kim, C. & Kim, Y. (2009). Acta Cryst. E65, m1045–m1046. Web of Science CSD CrossRef 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.