Bis[(1S,1'S)-1,1'-(4-amino-4H-1,2,4-triazole-3,5-di-yl)diethanol-κN]bis-(nitrato-κO)zinc.

In the title homochiral mononuclear compound, [Zn(NO(3))(2)(C(6)H(12)N(4)O(2))(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 NO(3) (-) anions, adopting a distorted tetra-hedral coordination geometry. The compound is enanti-omerically pure and corresponds to the S diastereoisomer, with the optical activity originating from the chiral ligand. In the crystal, mol-ecules are connected into three-dimensional supra-molecular 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 = 533.78

Tetragonal,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.088

S = 1.05

2463 reflections

154 parameters

378 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 993 Friedel pairs

Flack parameter: −0.022 (15)

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001754/ff2051sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn(NO3)2(C6H12N4O2)2]	Dx = 1.651 Mg m−3
Mr = 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

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

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(Fo2) + (0.0455P)2 + 0.2512P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2463 reflections	Δρmax = 0.32 e Å−3
154 parameters	Δρmin = −0.23 e Å−3
378 restraints	Absolute structure: Flack (1983), 993 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.022 (15)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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···O4iv	0.89	2.40	3.022 (4)	127

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⋯O4iv	0.89	2.40	3.022 (4)	127

Symmetry codes: (ii) ; (iii) ; (iv) .