A dimeric zinc(II) complex: bis­[μ-1,2-bis­(1,2,4-triazol-4-yl)ethane-κ2N1:N1′]bis­[dinitritozinc(II)]

Zhang, R.; Chen, Q.; Gao, J.; Wu, X.

doi:10.1107/S1600536810034203

metal-organic compounds

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Volume 66| Part 10| October 2010| Page m1208

doi:10.1107/S1600536810034203

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A dimeric zinc(II) complex: bis[μ-1,2-bis(1,2,4-triazol-4-yl)ethane-κ²N¹:N^1′]bis[dinitritozinc(II)]

Rongxian Zhang,^a ^* Qiuyun Chen,^a Jing Gao ^b and Xiangyang Wu ^a

^aSchool of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, People's Republic of China, and ^bSchool of Pharmacy, Jiangsu University, Zhenjiang 212013, People's Republic of China
^*Correspondence e-mail: rong@ujs.edu.cn

(Received 12 July 2010; accepted 25 August 2010; online 4 September 2010)

The coordination geometry of the Zn^II atom in the title complex, [Zn₂(NO₂)₄(C₆H₈N₆)₂], is distorted octahedral, 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 intermolecular 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 hydrogen bonding, see: Mascal (1998 ).

Experimental

Crystal data

[Zn₂(NO₂)₄(C₆H₈N₆)₂]
M_r = 643.15
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.104
S = 1.06
2144 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.61 e Å⁻³

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) $[-x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+2]$ .

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⋯N2^iv	0.93	2.39	3.314 (4)	176
Symmetry codes: (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

1,2,4-Triazole and its derivatives are very interesting ligands, because they combine the coordination geometry of both pyrazole and imidazole with regard to the arrangement of their three heteroatoms. A large number of mononuclear, oligonuclear and polynuclear transition metal complexes of 1,2,4-triazole derivatives have been synthesized and characterized because of their magnetic properties and novel topologies (Haasnoot, 2000).

In the present work, we report here the preparation and crystal structure of a dimeric zinc^II complex, namely, [Zn(btre)NO₂)₂]₂ (I) (btre = 1,2-bis(1,2,4-triazol-4-yl)ethane.

In the complex (I), the coordination geometry of the zinc^II atom in the title complex, [Zn(C₆H₈N₆)(NO₂)₂]₂ or [Zn(btre)(NO₂)₂]₂, where btre is µ-[1,2-bis(1,2,4-triazol-4-yl)ethane], is a distorted octahedron, in which the Zn^II atom is coordinated by two N atoms from the triazole rings of two symmetry-related btre ligands and four O atoms from two NO₂^- ligands. Two Zn^II atoms are bridged by two organic ligands to form a dimer. Each NO₂^- anion acts as a chelating coordination mode.

The crystal structure of (I) is built up from a neutral dimeric metallocycle. The dimer is centrosymmetric. As shown in Fig.1, in each dimer, two zinc^II centres are connected by two btre ligands resulting in a discrete Zn₂(btre)₂ 18-membered binuclear metallocycle.

Each zinc^II centre is six-coordinated by two N atoms of btre ligands and four O atoms from two NO₂^- ligands (Table 1), forming a distorted octahedral geometry. Each btre exhibits a gauche conformation in (I). The N3—C1—C2—N6 torsion angle is 64.9 (4)°. The dihedral angle between the two triazole ring is 40.1 (2)°. The Zn···Zn separation via the bridging btre ligand is 7.809 (2)Å in (I), compared with the corresponding values 7.8750 (2)Å in [Zn(btre)Cl₂]₂ and 7.7980 (5)Å in [Zn(btre)I₂]₂ (Habit et al., 2009).

Weak hydrogen bonds play an important role in the formation of the crystal structure. The intermolecular packing is organized by C—H···N and C—H···O hydrogen bonds (Table 2 and Figure 2; Mascal 1998).

Related literature top

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

Experimental top

A 10 ml aqueous solution of Zn(NO₂)₂ (1 mmol) was added to a tube, and a 10 ml MeOH solution of 1,2-bis(1,2,4-triazol-4-yl)ethane (btre) (1.0 mmol) was carefully added above the aqueous solution. Colourless crystal were obtained after about two weeks. Anal. Calcd. for C₁₂H₁₆N₁₆O₈Zn₂: C, 22.41; H, 2.51; N, 34.85%. Found: C, 22.36; H, 2.44; N, 34.69%.

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalClear (Rigaku, 2000); 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 dimeric structure of (I), with displacement ellipsoids drawn at the 30% probability level. [Symmetry code: A -x + 1/2, -y - 1/2, -z21.]
	Fig. 2. The cell packing of (I) along [010] direction.

bis[µ-1,2-bis(1,2,4-triazol-4-yl)ethane- κ²N¹:N^1']bis[dinitritozinc(II)] top

Crystal data top

[Zn₂(NO₂)₄(C₆H₈N₆)₂]	F(000) = 1296
M_r = 643.15	D_x = 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

Data collection top

Rigaku Mercury CCD diffractometer	2144 independent reflections
Radiation source: fine-focus sealed tube	1945 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 25.3°, θ_min = 3.2°
Absorption correction: multi-scan (Blessing, 1995, 1997)	h = −24→24
T_min = 0.364, T_max = 0.678	k = −7→8
10892 measured reflections	l = −20→20

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0627P)² + 2.1848P] where P = (F_o² + 2F_c²)/3
2144 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Zn₂(NO₂)₄(C₆H₈N₆)₂]	V = 2358.3 (8) Å³
M_r = 643.15	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 20.491 (4) Å	µ = 2.11 mm⁻¹
b = 6.7087 (13) Å	T = 293 K
c = 17.289 (4) Å	0.60 × 0.20 × 0.20 mm
β = 97.125 (5)°

Data collection top

Rigaku Mercury CCD diffractometer	2144 independent reflections
Absorption correction: multi-scan (Blessing, 1995, 1997)	1945 reflections with I > 2σ(I)
T_min = 0.364, T_max = 0.678	R_int = 0.036
10892 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	Δρ_max = 0.47 e Å⁻³
2144 reflections	Δρ_min = −0.61 e Å⁻³
172 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1/2, −y−1/2, −z+2.

Hydrogen-bond geometry (Å, º) top

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···N2^iv	0.93	2.39	3.314 (4)	176

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

Experimental details

Crystal data
Chemical formula	[Zn₂(NO₂)₄(C₆H₈N₆)₂]
M_r	643.15
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	20.491 (4), 6.7087 (13), 17.289 (4)
β (°)	97.125 (5)
V (Å³)	2358.3 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.11
Crystal size (mm)	0.60 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (Blessing, 1995, 1997)
T_min, T_max	0.364, 0.678
No. of measured, independent and observed [I > 2σ(I)] reflections	10892, 2144, 1945
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.104, 1.06
No. of reflections	2144
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.61

Computer programs: CrystalClear (Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

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

N4ⁱ—Zn1—O1	128.32 (12)	N1—Zn1—O2	89.42 (13)
N4ⁱ—Zn1—N1	103.43 (11)	O3—Zn1—O2	149.67 (12)
O1—Zn1—N1	107.96 (13)	N4ⁱ—Zn1—O4	86.27 (10)
N4ⁱ—Zn1—O3	119.46 (12)	O1—Zn1—O4	88.80 (12)
O1—Zn1—O3	97.34 (12)	N1—Zn1—O4	147.07 (10)
N1—Zn1—O3	95.48 (11)	O3—Zn1—O4	53.47 (10)
N4ⁱ—Zn1—O2	88.11 (11)	O2—Zn1—O4	122.68 (12)
O1—Zn1—O2	52.96 (11)

Symmetry code: (i) −x+1/2, −y−1/2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2ⁱⁱ	0.97	2.53	3.396 (5)	149.4
C2—H2A···O1ⁱⁱⁱ	0.97	2.49	3.417 (4)	160.1
C3—H3A···O2ⁱⁱ	0.93	2.66	3.412 (5)	138.7
C6—H6A···N2^iv	0.93	2.39	3.314 (4)	176.1

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

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. CrossRef CAS Web of Science IUCr Journals Google Scholar
Haasnoot, J. G. (2000). Coord. Chem. Rev. 200–202, 131–185. Web of Science CrossRef CAS Google Scholar
Habit, H. A., Hoffmann, A., Hoppe, H. A., Steinfeld, G. & Janiak, C. (2009). Inorg. Chem. 48, 2166–2180. Web of Science PubMed Google Scholar
Mascal, M. (1998). Chem. Commun. pp. 303–304. Web of Science CrossRef Google Scholar
Rigaku (2000). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Page m1208

doi:10.1107/S1600536810034203

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