A dimeric zinc(II) complex: bis-[μ-1,2-bis-(1,2,4-triazol-4-yl)ethane-κN:N]bis-[dinitritozinc(II)].

The coordination geometry of the Zn(II) atom in the title complex, [Zn(2)(NO(2))(4)(C(6)H(8)N(6))(2)], is distorted octa-hedral, in which the Zn(II) atom is coordinated by two N atoms from the triazole rings of two symmetry-related 1,2-bis-(1,2,4-triazol-4-yl)ethane ligands and four O atoms from two nitrite ligands. Two Zn(II) atoms are bridged by two organic ligands, forming a centrosymmetric dimer. Weak C-H⋯N and C-H⋯O hydrogen bonds play an important role in the inter-molecular packing.

Related literature

For background to 1,2,4-triazole and its derivatives, see: Haasnoot (2000 ▶). For a related structure, see: Habit et al. (2009 ▶). For n class="Chemical">hydrogen bonding, see: Mascal (1998 ▶).

Experimental

Crystal data

[Zn2(NO2)4(C6n class="Species">H8N6)2]

M = 643.15

Monoclinic,

a = 20.491 (4) Å

b = 6.7087 (13) Å

c = 17.289 (4) Å

β = 97.125 (5)°

V = 2358.3 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.11 mm−1

T = 293 K

0.60 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶, 1997 ▶) T min = 0.364, T max = 0.678

10892 measured reflections

2144 independent reflections

1945 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.06

2144 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.61 e Å−3

Data collection: CrystalClear (Rigaku, 2000 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034203/bv2153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034203/bv2153Isup2.hkl

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

[Zn2(NO2)4(C6H8N6)2]	F(000) = 1296
Mr = 643.15	Dx = 1.811 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -c 2yc	Cell parameters from 4261 reflections
a = 20.491 (4) Å	θ = 3.2–25.4°
b = 6.7087 (13) Å	µ = 2.11 mm−1
c = 17.289 (4) Å	T = 293 K
β = 97.125 (5)°	Block, colorless
V = 2358.3 (8) Å3	0.60 × 0.20 × 0.20 mm
Z = 4

Rigaku Mercury CCD diffractometer	2144 independent reflections
Radiation source: fine-focus sealed tube	1945 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 25.3°, θmin = 3.2°
Absorption correction: multi-scan (Blessing, 1995, 1997)	h = −24→24
Tmin = 0.364, Tmax = 0.678	k = −7→8
10892 measured reflections	l = −20→20

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0627P)2 + 2.1848P] where P = (Fo2 + 2Fc2)/3
2144 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.61 e Å−3

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	0.377036 (17)	0.06273 (5)	0.900523 (19)	0.03325 (17)
O1	0.42015 (16)	0.3236 (5)	0.8755 (2)	0.0767 (10)
O2	0.3646 (2)	0.3909 (5)	0.96266 (18)	0.0876 (12)
O3	0.40736 (13)	−0.1027 (4)	0.81217 (16)	0.0581 (7)
O4	0.48542 (14)	−0.1050 (5)	0.90120 (16)	0.0662 (8)
N1	0.28080 (13)	0.0744 (4)	0.85410 (15)	0.0353 (6)
N2	0.26438 (14)	0.0921 (4)	0.77408 (15)	0.0401 (7)
N3	0.17452 (13)	0.0807 (4)	0.83012 (15)	0.0325 (6)
N4	0.12627 (14)	−0.4368 (4)	0.99508 (15)	0.0353 (6)
N5	0.17231 (16)	−0.4949 (5)	0.94714 (18)	0.0499 (8)
N6	0.10563 (13)	−0.2736 (4)	0.88654 (14)	0.0355 (6)
N7	0.4027 (2)	0.4550 (5)	0.9200 (2)	0.0712 (11)
N8	0.46565 (16)	−0.1617 (6)	0.83561 (19)	0.0568 (8)
C1	0.10463 (16)	0.0757 (5)	0.8402 (2)	0.0413 (8)
H1A	0.0807	0.1668	0.8034	0.050*
H1B	0.0992	0.1202	0.8924	0.050*
C2	0.07634 (16)	−0.1309 (6)	0.82762 (19)	0.0448 (8)
H2A	0.0292	−0.1254	0.8292	0.054*
H2B	0.0837	−0.1775	0.7763	0.054*
C3	0.22636 (17)	0.0689 (5)	0.88560 (19)	0.0360 (7)
H3A	0.2237	0.0584	0.9388	0.043*
C4	0.20115 (17)	0.0957 (5)	0.76274 (18)	0.0392 (8)
H4A	0.1767	0.1072	0.7139	0.047*
C5	0.08740 (15)	−0.3056 (5)	0.95728 (17)	0.0330 (7)
H5A	0.0522	−0.2435	0.9766	0.040*
C6	0.15788 (19)	−0.3936 (6)	0.8829 (2)	0.0468 (9)
H6A	0.1808	−0.4031	0.8399	0.056*

	U11	U22	U33	U12	U13	U23
Zn1	0.0323 (3)	0.0385 (3)	0.0298 (2)	−0.00378 (14)	0.00707 (16)	0.00015 (14)
O1	0.080 (2)	0.0613 (18)	0.098 (2)	−0.0275 (16)	0.0486 (19)	−0.0208 (18)
O2	0.142 (4)	0.071 (2)	0.0574 (19)	−0.033 (2)	0.041 (2)	−0.0132 (16)
O3	0.0422 (16)	0.0766 (18)	0.0542 (16)	0.0062 (13)	0.0013 (12)	−0.0270 (14)
O4	0.0506 (18)	0.098 (2)	0.0485 (16)	−0.0159 (16)	0.0018 (13)	−0.0053 (15)
N1	0.0298 (15)	0.0439 (16)	0.0322 (14)	−0.0011 (11)	0.0038 (11)	0.0003 (11)
N2	0.0341 (16)	0.0556 (17)	0.0321 (14)	0.0014 (13)	0.0100 (12)	0.0078 (12)
N3	0.0279 (14)	0.0353 (14)	0.0354 (14)	0.0019 (10)	0.0083 (11)	0.0064 (11)
N4	0.0377 (15)	0.0387 (15)	0.0309 (14)	−0.0026 (11)	0.0097 (12)	−0.0004 (11)
N5	0.052 (2)	0.0539 (17)	0.0480 (18)	0.0126 (15)	0.0243 (15)	0.0090 (15)
N6	0.0336 (14)	0.0440 (15)	0.0293 (13)	−0.0075 (12)	0.0056 (11)	0.0035 (11)
N7	0.110 (3)	0.0459 (19)	0.062 (2)	−0.022 (2)	0.028 (2)	−0.0096 (17)
N8	0.0402 (18)	0.078 (2)	0.0531 (19)	0.0002 (17)	0.0121 (15)	−0.0140 (17)
C1	0.0286 (17)	0.056 (2)	0.0415 (18)	0.0098 (14)	0.0106 (14)	0.0181 (15)
C2	0.0274 (17)	0.074 (2)	0.0320 (17)	−0.0075 (17)	−0.0009 (13)	0.0115 (17)
C3	0.0348 (18)	0.0455 (19)	0.0287 (15)	0.0005 (14)	0.0082 (13)	−0.0004 (13)
C4	0.0374 (19)	0.0522 (19)	0.0285 (16)	0.0049 (15)	0.0060 (14)	0.0088 (14)
C5	0.0317 (17)	0.0392 (16)	0.0290 (15)	−0.0046 (14)	0.0072 (12)	−0.0003 (13)
C6	0.053 (2)	0.053 (2)	0.0378 (18)	0.0008 (17)	0.0219 (16)	0.0017 (16)

Zn1—N4i	2.002 (3)	N4—C5	1.307 (4)
Zn1—O1	2.031 (3)	N4—N5	1.386 (4)
Zn1—N1	2.036 (3)	N4—Zn1i	2.002 (3)
Zn1—O3	2.046 (3)	N5—C6	1.304 (5)
Zn1—O2	2.477 (3)	N6—C5	1.340 (4)
Zn1—O4	2.488 (3)	N6—C6	1.347 (5)
O1—N7	1.251 (4)	N6—C2	1.471 (4)
O2—N7	1.218 (5)	C1—C2	1.508 (5)
O3—N8	1.276 (4)	C1—H1A	0.9700
O4—N8	1.217 (4)	C1—H1B	0.9700
N1—C3	1.301 (4)	C2—H2A	0.9700
N1—N2	1.388 (4)	C2—H2B	0.9700
N2—C4	1.286 (4)	C3—H3A	0.9300
N3—C3	1.342 (4)	C4—H4A	0.9300
N3—C4	1.350 (4)	C5—H5A	0.9300
N3—C1	1.464 (4)	C6—H6A	0.9300
N4i—Zn1—O1	128.32 (12)	C5—N6—C6	105.1 (3)
N4i—Zn1—N1	103.43 (11)	C5—N6—C2	126.9 (3)
O1—Zn1—N1	107.96 (13)	C6—N6—C2	128.0 (3)
N4i—Zn1—O3	119.46 (12)	O2—N7—O1	112.2 (3)
O1—Zn1—O3	97.34 (12)	O4—N8—O3	112.9 (3)
N1—Zn1—O3	95.48 (11)	N3—C1—C2	111.6 (3)
N4i—Zn1—O2	88.11 (11)	N3—C1—H1A	109.3
O1—Zn1—O2	52.96 (11)	C2—C1—H1A	109.3
N1—Zn1—O2	89.42 (13)	N3—C1—H1B	109.3
O3—Zn1—O2	149.67 (12)	C2—C1—H1B	109.3
N4i—Zn1—O4	86.27 (10)	H1A—C1—H1B	108.0
O1—Zn1—O4	88.80 (12)	N6—C2—C1	112.5 (3)
N1—Zn1—O4	147.07 (10)	N6—C2—H2A	109.1
O3—Zn1—O4	53.47 (10)	C1—C2—H2A	109.1
O2—Zn1—O4	122.68 (12)	N6—C2—H2B	109.1
N7—O1—Zn1	108.1 (2)	C1—C2—H2B	109.1
N7—O2—Zn1	86.7 (2)	H2A—C2—H2B	107.8
N8—O3—Zn1	106.9 (2)	N1—C3—N3	110.1 (3)
N8—O4—Zn1	86.7 (2)	N1—C3—H3A	125.0
C3—N1—N2	107.8 (3)	N3—C3—H3A	125.0
C3—N1—Zn1	132.3 (2)	N2—C4—N3	112.0 (3)
N2—N1—Zn1	120.0 (2)	N2—C4—H4A	124.0
C4—N2—N1	105.6 (3)	N3—C4—H4A	124.0
C3—N3—C4	104.6 (3)	N4—C5—N6	110.0 (3)
C3—N3—C1	127.8 (3)	N4—C5—H5A	125.0
C4—N3—C1	127.6 (3)	N6—C5—H5A	125.0
C5—N4—N5	107.9 (3)	N5—C6—N6	111.6 (3)
C5—N4—Zn1i	130.4 (2)	N5—C6—H6A	124.2
N5—N4—Zn1i	121.5 (2)	N6—C6—H6A	124.2
C6—N5—N4	105.3 (3)
N4i—Zn1—O1—N7	−48.4 (4)	O4—Zn1—N1—N2	−55.0 (3)
N1—Zn1—O1—N7	76.1 (3)	C3—N1—N2—C4	−0.1 (4)
O3—Zn1—O1—N7	174.4 (3)	Zn1—N1—N2—C4	−180.0 (2)
O2—Zn1—O1—N7	1.1 (3)	C5—N4—N5—C6	0.0 (4)
O4—Zn1—O1—N7	−132.7 (3)	Zn1i—N4—N5—C6	176.0 (2)
N4i—Zn1—O2—N7	142.3 (3)	Zn1—O2—N7—O1	1.5 (4)
O1—Zn1—O2—N7	−1.1 (3)	Zn1—O1—N7—O2	−1.9 (5)
N1—Zn1—O2—N7	−114.3 (3)	Zn1—O4—N8—O3	−0.1 (3)
O3—Zn1—O2—N7	−14.4 (5)	Zn1—O3—N8—O4	0.1 (4)
O4—Zn1—O2—N7	57.9 (3)	C3—N3—C1—C2	−96.2 (4)
N4i—Zn1—O3—N8	−59.3 (3)	C4—N3—C1—C2	82.9 (4)
O1—Zn1—O3—N8	82.9 (3)	C5—N6—C2—C1	84.7 (4)
N1—Zn1—O3—N8	−168.1 (3)	C6—N6—C2—C1	−92.2 (4)
O2—Zn1—O3—N8	93.6 (3)	N3—C1—C2—N6	64.9 (4)
O4—Zn1—O3—N8	−0.1 (2)	N2—N1—C3—N3	0.4 (3)
N4i—Zn1—O4—N8	131.5 (2)	Zn1—N1—C3—N3	−179.7 (2)
O1—Zn1—O4—N8	−100.0 (3)	C4—N3—C3—N1	−0.6 (3)
N1—Zn1—O4—N8	22.4 (3)	C1—N3—C3—N1	178.7 (3)
O3—Zn1—O4—N8	0.1 (2)	N1—N2—C4—N3	−0.2 (4)
O2—Zn1—O4—N8	−143.1 (2)	C3—N3—C4—N2	0.5 (4)
N4i—Zn1—N1—C3	21.0 (3)	C1—N3—C4—N2	−178.7 (3)
O1—Zn1—N1—C3	−117.4 (3)	N5—N4—C5—N6	−0.1 (4)
O3—Zn1—N1—C3	143.0 (3)	Zn1i—N4—C5—N6	−175.7 (2)
O2—Zn1—N1—C3	−67.0 (3)	C6—N6—C5—N4	0.3 (4)
O4—Zn1—N1—C3	125.2 (3)	C2—N6—C5—N4	−177.2 (3)
N4i—Zn1—N1—N2	−159.2 (2)	N4—N5—C6—N6	0.2 (4)
O1—Zn1—N1—N2	62.4 (2)	C5—N6—C6—N5	−0.3 (4)
O3—Zn1—N1—N2	−37.2 (2)	C2—N6—C6—N5	177.1 (3)
O2—Zn1—N1—N2	112.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2ii	0.97	2.53	3.396 (5)	149
C2—H2A···O1iii	0.97	2.49	3.417 (4)	160
C3—H3A···O2ii	0.93	2.66	3.412 (5)	139
C6—H6A···N2iv	0.93	2.39	3.314 (4)	176

Table 1

Selected bond lengths (Å)

Zn1—N4i	2.002 (3)
Zn1—O1	2.031 (3)
Zn1—N1	2.036 (3)
Zn1—O3	2.046 (3)
Zn1—O2	2.477 (3)
Zn1—O4	2.488 (3)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O2ii	0.97	2.53	3.396 (5)	149
C2—H2A⋯O1iii	0.97	2.49	3.417 (4)	160
C3—H3A⋯O2ii	0.93	2.66	3.412 (5)	139
C6—H6A⋯N2iv	0.93	2.39	3.314 (4)	176

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