Bis[(1S,1′S)-1,1′-(4-amino-4H-1,2,4-triazole-3,5-di­yl)diethanol-κN1]bis­(nitrato-κO)zinc

Liu, X.-G.; Shen, L.; Cai, Q.-S.; Luo, M.

doi:10.1107/S1600536812001754

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages m191-m192

doi:10.1107/S1600536812001754

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Bis[(1S,1′S)-1,1′-(4-amino-4H-1,2,4-triazole-3,5-diyl)diethanol-κN¹]bis(nitrato-κO)zinc

Xun-Gao Liu,^a,^b ^* Liang Shen,^a Qi-Suo Cai ^a and Ma Luo ^a

^aCollege of Material Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, People's Republic of China, and ^bState Key Laboratory of Coordination Chemistry, Coordination Chemistry Institute, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: xgliu07@gmail.com

(Received 4 January 2012; accepted 14 January 2012; online 21 January 2012)

In the title homochiral mononuclear compound, [Zn(NO₃)₂(C₆H₁₂N₄O₂)₂], the Zn^II atom is located on a twofold rotation axis and coordinated by two N atoms from two ligands and two O atoms from two NO₃⁻ anions, adopting a distorted tetrahedral coordination geometry. The compound is enantiomerically pure and corresponds to the S diastereoisomer, with the optical activity originating from the chiral ligand. In the crystal, molecules are connected into three-dimensional supramolecular networks through O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds.

Related literature

For 4-amino-4H-1,2,4-triazole transition metal complexes, see: Zhai et al. (2006 ); Yi et al. (2004 ). For the non-linear optical properties of chiral coordination compounds, see: Evans & Lin (2002 ). For uses of chiral coordination compounds, see: Hang et al. (2011 ); Lin (2010 ).

Experimental

Crystal data

[Zn(NO₃)₂(C₆H₁₂N₄O₂)₂]
M_r = 533.78
Tetragonal, P 4₁ 2₁ 2
a = 12.1252 (7) Å
c = 14.6108 (17) Å
V = 2148.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.22 mm⁻¹
T = 298 K
0.36 × 0.18 × 0.12 mm

Data collection

Bruker APEX DUO diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.767, T_max = 0.862
7446 measured reflections
2463 independent reflections
2154 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.088
S = 1.05
2463 reflections
154 parameters
378 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 993 Friedel pairs
Flack parameter: −0.022 (15)

Table 1
Selected geometric parameters (Å, °)

Zn1—N1	2.0239 (19)
Zn1—O3	2.071 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱⁱ	0.82	2.07	2.867 (3)	163
N4—H4B⋯O5ⁱⁱ	0.89	2.51	3.142 (5)	129
O2—H2⋯N2ⁱⁱⁱ	0.82	2.13	2.943 (3)	174
N4—H4C⋯O4^iv	0.89	2.40	3.022 (4)	127
Symmetry codes: (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+{\script{7\over 4}}]$ ; (iii) $[-y+2, -x+2, -z+{\script{3\over 2}}]$ ; (iv) $[-x+2, -y+2, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg & Putz, 2007 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812001754/ff2051sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001754/ff2051Isup2.hkl

checkCIF report

Comment top

Chiral coordination complexes have received considerable attention due to their potential applications in the area of ferroelectrics, enantiopure catalysis and separation (Hang et al., 2011; Lin et al., 2010). Among the different approaches to synthesize chiral coordination compounds, the most effective synthetic strategy is to use optically pure chiral ligands. Herein, we report a chiral zinc coordination compound (S)-[Zn(deoatrz)₂(NO₃)₂], by using an enantiopure (1S,1'S)-1,1'-(4-amino-4H-1,2,4-triazole-3,5-diyl)diethanol (deoatrz), reacting with zinc salts. Furthermore, its structure is characterized.

Single crystal structural analysis reveals that the title compound crystallizes in the tetragonal system, chiral space group P4₁2₁2. The title compound is a mononuclear and its asymmetric unit consists of one Zn atom, two deoatrz ligands and two NO₃– anions (Fig. 1). The Zn atom is coordinated by two N atoms (N1, N1A) from two deoatrz ligands and two NO₃– anions (O3, O3A), adopting a distorted tetrahedral coordination geometry. The Zn—O and Zn—N bond lengths are 2.071 (2) and 2.024 (1) Å, respectively. The bond angles around Zn atom vary from 95.9 (8) to 143.5 (1)^o.

As shown in Fig. 2, the interesting H-bonds are observed in the title compound. The fundamentally units are one dimensional chiral hydrogen bond chains along c axis, and subsequently the chains are connected into three-dimensional chiral supramolecular networks through O—H···O, O—H···N and N—H···O hydrogen bond interactions.

Related literature top

For 4-amino-4H-1,2,4-triazole transition metal complexes, see: Zhai et al. (2006); Yi et al. (2004). For the non-linear optical properties of chiral coordination compounds, see: Evans & Lin (2002). For uses of chiral coordination compounds, see: Hang et al. (2011); Lin (2010).

Experimental top

An 10 ml ethanol solution of (1S,1'S)-1,1'-(4-amino-4H-1,2,4-triazole -3,5-diyl)diethanol (0.2 mmol, 0.0344 g) and Zn(NO₃)₂.₆H₂O (0.10 mmol, 0.0298 g) was stirred for five minutes and then filtered. The filtrate was carefully layered with 10 ml ethyl ether. After one week, colorless needle-like crystals of the title compound were obtained. Yield: 45%.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Putz, 2007); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Coordination geometry of Znic in the title compound with atomic labeling scheme. Thermal ellipsoids are at the 30% probability level. All H atoms except those attached to O and N atoms are omitted for clarity.
	Fig. 2. The hydrogen-bonded chains in the title compound along the c axis.
	Fig. 3. Three dimensional hydrogen-bonded supramolecular networks in the title compound Viewed from c dimension.

Bis[(1S,1'S)-1,1'-(4-amino-4H-1,2,4-triazole-3,5- diyl)diethanol-κN¹]bis(nitrato-κO)zinc top

Crystal data top

[Zn(NO₃)₂(C₆H₁₂N₄O₂)₂]	D_x = 1.651 Mg m⁻³
M_r = 533.78	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₁2₁2	Cell parameters from 7446 reflections
Hall symbol: P 4abw 2nw	θ = 1.7–27.5°
a = 12.1252 (7) Å	µ = 1.22 mm⁻¹
c = 14.6108 (17) Å	T = 298 K
V = 2148.1 (3) Å³	Needle, colourless
Z = 4	0.36 × 0.18 × 0.12 mm
F(000) = 1104

Data collection top

Bruker APEX DUO diffractometer	2463 independent reflections
Radiation source: fine-focus sealed tube	2154 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→9
T_min = 0.767, T_max = 0.862	k = −15→13
7446 measured reflections	l = −18→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0455P)² + 0.2512P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2463 reflections	Δρ_max = 0.32 e Å⁻³
154 parameters	Δρ_min = −0.23 e Å⁻³
378 restraints	Absolute structure: Flack (1983), 993 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.022 (15)

Crystal data top

[Zn(NO₃)₂(C₆H₁₂N₄O₂)₂]	Z = 4
M_r = 533.78	Mo Kα radiation
Tetragonal, P4₁2₁2	µ = 1.22 mm⁻¹
a = 12.1252 (7) Å	T = 298 K
c = 14.6108 (17) Å	0.36 × 0.18 × 0.12 mm
V = 2148.1 (3) Å³

Data collection top

Bruker APEX DUO diffractometer	2463 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2154 reflections with I > 2σ(I)
T_min = 0.767, T_max = 0.862	R_int = 0.032
7446 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.088	Δρ_max = 0.32 e Å⁻³
S = 1.05	Δρ_min = −0.23 e Å⁻³
2463 reflections	Absolute structure: Flack (1983), 993 Friedel pairs
154 parameters	Absolute structure parameter: −0.022 (15)
378 restraints

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
Zn1	0.92340 (3)	0.92340 (3)	1.0000	0.03222 (13)
O1	0.72436 (18)	0.90461 (18)	0.95521 (12)	0.0417 (5)
H1	0.7021	0.8493	0.9817	0.063*
O2	1.13628 (15)	0.75723 (17)	0.67187 (13)	0.0336 (4)
H2	1.1479	0.8235	0.6777	0.050*
O3	1.09002 (17)	0.89583 (19)	1.02136 (13)	0.0464 (5)
O4	1.0802 (3)	1.0273 (3)	1.1173 (3)	0.1176 (14)
O5	1.2371 (2)	0.9742 (3)	1.0727 (2)	0.0758 (9)
N1	0.91797 (19)	0.85483 (18)	0.87379 (13)	0.0285 (5)
N2	1.00505 (19)	0.81575 (19)	0.82025 (13)	0.0279 (5)
N3	0.84957 (17)	0.80180 (17)	0.74473 (15)	0.0271 (4)
N4	0.7738 (2)	0.7823 (2)	0.67330 (16)	0.0427 (6)
H4B	0.7928	0.7208	0.6440	0.064*
H4C	0.7753	0.8388	0.6345	0.064*
N5	1.1372 (2)	0.9678 (2)	1.07029 (17)	0.0417 (6)
C1	0.8266 (2)	0.8474 (2)	0.82697 (16)	0.0273 (5)
C2	0.9608 (2)	0.7841 (2)	0.74215 (16)	0.0262 (5)
C3	0.7171 (2)	0.8883 (2)	0.85876 (17)	0.0332 (6)
H3	0.6595	0.8343	0.8446	0.040*
C4	0.6903 (3)	0.9988 (3)	0.8141 (2)	0.0467 (8)
H4D	0.6216	1.0261	0.8377	0.070*
H4E	0.6844	0.9892	0.7490	0.070*
H4F	0.7479	1.0507	0.8274	0.070*
C5	1.0219 (2)	0.7390 (2)	0.66148 (17)	0.0299 (6)
H5	0.9968	0.7776	0.6063	0.036*
C6	1.0044 (3)	0.6164 (3)	0.6482 (2)	0.0460 (8)
H6A	1.0389	0.5934	0.5923	0.069*
H6B	0.9268	0.6011	0.6452	0.069*
H6C	1.0363	0.5770	0.6987	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03548 (17)	0.03548 (17)	0.02569 (18)	0.0024 (2)	0.00483 (13)	−0.00483 (13)
O1	0.0449 (12)	0.0468 (14)	0.0334 (9)	−0.0032 (10)	0.0117 (9)	0.0021 (9)
O2	0.0277 (10)	0.0310 (11)	0.0420 (9)	0.0005 (8)	0.0038 (8)	−0.0056 (9)
O3	0.0380 (12)	0.0514 (13)	0.0497 (10)	0.0025 (9)	−0.0045 (9)	−0.0172 (9)
O4	0.0629 (19)	0.112 (3)	0.178 (3)	0.0013 (19)	−0.005 (2)	−0.105 (3)
O5	0.0356 (15)	0.102 (2)	0.0901 (18)	0.0029 (14)	−0.0133 (13)	−0.0283 (17)
N1	0.0269 (11)	0.0310 (11)	0.0277 (9)	0.0003 (10)	0.0016 (9)	−0.0025 (8)
N2	0.0260 (11)	0.0307 (11)	0.0269 (9)	0.0038 (9)	−0.0002 (8)	−0.0031 (8)
N3	0.0242 (10)	0.0296 (10)	0.0275 (8)	−0.0036 (8)	−0.0028 (9)	−0.0012 (9)
N4	0.0409 (14)	0.0495 (16)	0.0378 (10)	−0.0041 (11)	−0.0161 (11)	−0.0046 (12)
N5	0.0369 (15)	0.0375 (14)	0.0508 (13)	0.0048 (11)	−0.0053 (11)	−0.0062 (12)
C1	0.0282 (13)	0.0250 (13)	0.0288 (10)	−0.0015 (10)	0.0020 (10)	0.0035 (10)
C2	0.0265 (11)	0.0248 (12)	0.0272 (10)	−0.0010 (9)	−0.0026 (10)	0.0020 (10)
C3	0.0265 (14)	0.0394 (15)	0.0336 (11)	−0.0004 (11)	0.0022 (10)	0.0016 (11)
C4	0.0406 (18)	0.0481 (19)	0.0515 (16)	0.0162 (15)	0.0033 (14)	0.0044 (15)
C5	0.0278 (13)	0.0339 (14)	0.0281 (10)	0.0028 (11)	−0.0015 (10)	−0.0028 (10)
C6	0.0423 (18)	0.0410 (18)	0.0546 (17)	−0.0048 (15)	0.0031 (15)	−0.0171 (14)

Geometric parameters (Å, º) top

Zn1—N1	2.0239 (19)	N3—N4	1.410 (3)
Zn1—N1ⁱ	2.0239 (19)	N4—H4B	0.8900
Zn1—O3	2.071 (2)	N4—H4C	0.8900
Zn1—O3ⁱ	2.071 (2)	C1—C3	1.492 (4)
O1—C3	1.426 (3)	C2—C5	1.496 (4)
O1—H1	0.8200	C3—C4	1.525 (4)
O2—C5	1.412 (3)	C3—H3	0.9800
O2—H2	0.8200	C4—H4D	0.9600
O3—N5	1.265 (3)	C4—H4E	0.9600
O4—N5	1.212 (4)	C4—H4F	0.9600
O5—N5	1.215 (4)	C5—C6	1.514 (4)
N1—C1	1.305 (3)	C5—H5	0.9800
N1—N2	1.397 (3)	C6—H6A	0.9600
N2—C2	1.318 (3)	C6—H6B	0.9600
N3—C1	1.352 (3)	C6—H6C	0.9600
N3—C2	1.366 (3)

N1—Zn1—N1ⁱ	143.46 (13)	N2—C2—C5	125.9 (2)
N1—Zn1—O3	95.90 (8)	N3—C2—C5	124.6 (2)
N1ⁱ—Zn1—O3	104.96 (8)	O1—C3—C1	107.4 (2)
N1—Zn1—O3ⁱ	104.96 (8)	O1—C3—C4	108.4 (2)
N1ⁱ—Zn1—O3ⁱ	95.90 (8)	C1—C3—C4	110.4 (2)
O3—Zn1—O3ⁱ	109.73 (13)	O1—C3—H3	110.2
C3—O1—H1	109.5	C1—C3—H3	110.2
C5—O2—H2	109.5	C4—C3—H3	110.2
N5—O3—Zn1	114.52 (17)	C3—C4—H4D	109.5
C1—N1—N2	108.94 (19)	C3—C4—H4E	109.5
C1—N1—Zn1	122.26 (18)	H4D—C4—H4E	109.5
N2—N1—Zn1	128.68 (16)	C3—C4—H4F	109.5
C2—N2—N1	106.0 (2)	H4D—C4—H4F	109.5
C1—N3—C2	107.0 (2)	H4E—C4—H4F	109.5
C1—N3—N4	126.3 (2)	O2—C5—C2	110.2 (2)
C2—N3—N4	126.6 (2)	O2—C5—C6	107.8 (2)
N3—N4—H4B	109.2	C2—C5—C6	113.0 (2)
N3—N4—H4C	109.2	O2—C5—H5	108.6
H4B—N4—H4C	109.5	C2—C5—H5	108.6
O4—N5—O5	120.9 (3)	C6—C5—H5	108.6
O4—N5—O3	118.2 (3)	C5—C6—H6A	109.5
O5—N5—O3	120.8 (3)	C5—C6—H6B	109.5
N1—C1—N3	108.6 (2)	H6A—C6—H6B	109.5
N1—C1—C3	124.7 (2)	C5—C6—H6C	109.5
N3—C1—C3	126.6 (2)	H6A—C6—H6C	109.5
N2—C2—N3	109.4 (2)	H6B—C6—H6C	109.5

Symmetry code: (i) y, x, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱⁱ	0.82	2.07	2.867 (3)	163
N4—H4B···O5ⁱⁱ	0.89	2.51	3.142 (5)	129
O2—H2···N2ⁱⁱⁱ	0.82	2.13	2.943 (3)	174
N4—H4C···O4^iv	0.89	2.40	3.022 (4)	127

Symmetry codes: (ii) x−1/2, −y+3/2, −z+7/4; (iii) −y+2, −x+2, −z+3/2; (iv) −x+2, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Zn(NO₃)₂(C₆H₁₂N₄O₂)₂]
M_r	533.78
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	298
a, c (Å)	12.1252 (7), 14.6108 (17)
V (Å³)	2148.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.22
Crystal size (mm)	0.36 × 0.18 × 0.12

Data collection
Diffractometer	Bruker APEX DUO diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.767, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	7446, 2463, 2154
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.088, 1.05
No. of reflections	2463
No. of parameters	154
No. of restraints	378
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.23
Absolute structure	Flack (1983), 993 Friedel pairs
Absolute structure parameter	−0.022 (15)

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Putz, 2007).

Selected geometric parameters (Å, º) top

Zn1—N1	2.0239 (19)	Zn1—O3	2.071 (2)
Zn1—N1ⁱ	2.0239 (19)	Zn1—O3ⁱ	2.071 (2)

N1—Zn1—N1ⁱ	143.46 (13)	N1—Zn1—O3ⁱ	104.96 (8)
N1—Zn1—O3	95.90 (8)	N1ⁱ—Zn1—O3ⁱ	95.90 (8)
N1ⁱ—Zn1—O3	104.96 (8)	O3—Zn1—O3ⁱ	109.73 (13)

Symmetry code: (i) y, x, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱⁱ	0.82	2.07	2.867 (3)	163.4
N4—H4B···O5ⁱⁱ	0.89	2.51	3.142 (5)	128.9
O2—H2···N2ⁱⁱⁱ	0.82	2.13	2.943 (3)	174.4
N4—H4C···O4^iv	0.89	2.40	3.022 (4)	127.0

Symmetry codes: (ii) x−1/2, −y+3/2, −z+7/4; (iii) −y+2, −x+2, −z+3/2; (iv) −x+2, −y+2, z−1/2.

Acknowledgements

The authors thank Yuan Deng for collecting the X-ray crystal data. We are also grateful to the National Natural Science Foundation of China (21101048), the Qianjiang Talent Projects of Zhejiang Province (2011R10091), the Education Office of Zhejiang Province (201065XP139) and Hangzhou Normal University (HSKQ0007) for financial support.

References

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