Poly[(μ2-azido-κ2N1:N1)[μ2-5-(8-quinolyl­oxy­methyl)tetra­zolato-κ4N1,O,N5:N4]zinc(II)]

Cai, H.

doi:10.1107/S1600536809016924

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page m632

doi:10.1107/S1600536809016924

Open

access

Poly[(μ₂-azido-κ²N¹:N¹)[μ₂-5-(8-quinolyloxymethyl)tetrazolato-κ⁴N¹,O,N⁵:N⁴]zinc(II)]

Hong-ling Cai ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: seuwangwei@gmail.com

(Received 14 April 2009; accepted 5 May 2009; online 14 May 2009)

In the title compound, [Zn(C₁₁H₈N₅O)(N₃)]_n, the Zn atom is hexacoordinated by five N atoms and one O atom in a distorted octahedral geometry. The chelating 5-(8-quinolyloxymethyl)tetrazolate ligands are approximately planar, with a dihedral angle of 3.6 (2)° between the quinoline and tetrazole planes. Adjacent Zn atoms are linked by two bridging azide ligands across a centre of inversion, and further coordination by one N atom of an adjacent tetrazole unit forms two-dimensional frameworks in (100). C—H⋯N interactions exist between ligands in neighbouring layers.

Related literature

For the use of tetrazole derivatives in coordination chemistry, see: Wang et al. (2005 ); Xiong et al. (2002 ). For details of the synthetis, see: Luo & Ye (2008 ). For related structures, see: Wang & Ye (2008 ); Chen & Ye (2008 ).

Experimental

Crystal data

[Zn(C₁₁H₈N₅O)(N₃)]
M_r = 333.64
Monoclinic, P 2₁ /c
a = 10.352 (8) Å
b = 14.108 (9) Å
c = 8.626 (8) Å
β = 90.31 (2)°
V = 1259.8 (17) Å³
Z = 4
Mo Kα radiation
μ = 1.96 mm⁻¹
T = 294 K
0.18 × 0.12 × 0.10 mm

Data collection

Rigaku SCXmini CCD diffractometer
Absorption correction: multi-scan CrystalClear (Rigaku, 2005 ) T_min = 0.714, T_max = 0.821
11540 measured reflections
2714 independent reflections
2261 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.183
S = 1.19
2714 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯N2ⁱ	0.93	2.49	3.411 (8)	170
C11—H11B⋯N8ⁱⁱ	0.97	2.54	3.252 (7)	130
Symmetry codes: (i) x-1, y, z; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); 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 I, global. DOI: 10.1107/S1600536809016924/bi2367sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016924/bi2367Isup2.hkl

checkCIF report

Comment top

As shown in Fig. 1, the Zn atom adopts a distorted octahedral coordination geometry, coordinated by one N atom and one O atom from 8-hydroxyquinoline, two N atoms from two different tetrazole groups and two N atoms from two bridging azide groups. Thus, 8-[(1H-tetrazol-5-yl)methoxy]quinoline acts as a tetradentate linker while the azide groups bridge between Zn atoms to form centrosymmetric rhombic units. Two-dimensional frameworks are formed in the (100) planes, and C—H···N interactions exist between ligands in neighbouring planes.

Related literature top

For the use of tetrazole derivatives in coordination chemistry, see: Wang et al. (2005); Xiong et al. (2002). For details of the synthetis, see: Luo & Ye (2008). For related structures, see: Wang & Ye (2008); Chen & Ye (2008).

Experimental top

A mixture of quinolin-8-ol (1.45 g, 10 mmol), 1.38 g K₂CO₃, 30 ml acetone and 2-bromoacetonitrile (1.32 g,11 mmol) was refluxed overnight. After cooling, the resulting dark mixture was extracted with ether (30 ml) and the solvent was removed at reduced pressure to give a crude product. Recrystallization from ethanol gave the pure ligand 2-(quinolin-8-yloxy)acetonitrile as a white powder. A mixture of this ligand (0.037 g, 0.2 mmol), ZnCl₂ (0.026 g, 0.2 mmol) and water (1 ml) was sealed in a glass tube and maintained at 383 K. Yellow crystals of the title compound suitable for X-ray analysis were obtained after 3 d.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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. Molecular structure with displacement ellipsoids drawn at the 30% probability level. H atoms are omitted. Symmetry code: (A) 2 - x, 2 - y, -z.
	Fig. 2. Packing diagram viewed along the a axis.

Poly[(µ₂-azido-κ²N¹:N¹)[µ₂-5-(8-quinolyloxymethyl)tetrazolato- κ⁴N¹,O,N⁵:N⁴]zinc(II)] top

Crystal data top

[Zn(C₁₁H₈N₅O)(N₃)]	F(000) = 672
M_r = 333.64	D_x = 1.759 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3428 reflections
a = 10.352 (8) Å	θ = 2.0–27.3°
b = 14.108 (9) Å	µ = 1.96 mm⁻¹
c = 8.626 (8) Å	T = 294 K
β = 90.31 (2)°	Block, pale yellow
V = 1259.8 (17) Å³	0.18 × 0.12 × 0.10 mm
Z = 4

Data collection top

Rigaku SCXmini CCD diffractometer	2714 independent reflections
Radiation source: fine-focus sealed tube	2261 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ω scans	θ_max = 27.3°, θ_min = 2.0°
Absorption correction: multi-scan CrystalClear (Rigaku, 2005)	h = −13→13
T_min = 0.714, T_max = 0.821	k = −18→18
11540 measured reflections	l = −11→11

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0764P)²] where P = (F_o² + 2F_c²)/3
2714 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

[Zn(C₁₁H₈N₅O)(N₃)]	V = 1259.8 (17) Å³
M_r = 333.64	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.352 (8) Å	µ = 1.96 mm⁻¹
b = 14.108 (9) Å	T = 294 K
c = 8.626 (8) Å	0.18 × 0.12 × 0.10 mm
β = 90.31 (2)°

Data collection top

Rigaku SCXmini CCD diffractometer	2714 independent reflections
Absorption correction: multi-scan CrystalClear (Rigaku, 2005)	2261 reflections with I > 2σ(I)
T_min = 0.714, T_max = 0.821	R_int = 0.059
11540 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.183	H-atom parameters constrained
S = 1.19	Δρ_max = 0.63 e Å⁻³
2714 reflections	Δρ_min = −0.71 e Å⁻³
190 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	0.95242 (4)	0.90443 (3)	0.09995 (5)	0.0298 (2)
N5	0.7775 (3)	0.9622 (3)	0.1958 (4)	0.0347 (8)
N1	1.0142 (3)	0.7920 (3)	−0.0386 (4)	0.0374 (8)
O1	0.7733 (3)	0.8144 (2)	0.0151 (4)	0.0420 (8)
C9	0.6528 (4)	0.8458 (3)	0.0556 (5)	0.0343 (9)
C8	0.5420 (4)	0.9627 (4)	0.2162 (6)	0.0447 (11)
C7	0.7806 (5)	1.0369 (3)	0.2914 (5)	0.0433 (11)
H7A	0.8605	1.0629	0.3173	0.052*
C6	0.6587 (4)	0.9259 (3)	0.1565 (5)	0.0326 (9)
C5	0.4240 (5)	0.9206 (4)	0.1716 (8)	0.0595 (15)
H5A	0.3469	0.9447	0.2100	0.071*
C4	0.5380 (4)	0.8062 (3)	0.0114 (6)	0.0471 (11)
H4A	0.5366	0.7553	−0.0571	0.056*
C3	0.4212 (5)	0.8432 (4)	0.0705 (8)	0.0621 (15)
H3A	0.3427	0.8161	0.0421	0.075*
C2	0.5503 (5)	1.0407 (4)	0.3162 (6)	0.0551 (14)
H2A	0.4755	1.0674	0.3566	0.066*
C11	0.7891 (4)	0.7426 (3)	−0.0998 (5)	0.0340 (9)
H11A	0.7493	0.7611	−0.1973	0.041*
H11B	0.7521	0.6829	−0.0661	0.041*
N2	1.1345 (4)	0.7624 (3)	−0.0749 (5)	0.0488 (10)
C10	0.9352 (4)	0.7353 (3)	−0.1149 (5)	0.0319 (8)
N6	1.0849 (3)	1.0102 (3)	0.1218 (4)	0.0351 (8)
N3	1.1247 (4)	0.6921 (3)	−0.1722 (5)	0.0504 (11)
C1	0.6690 (6)	1.0780 (4)	0.3545 (7)	0.0538 (13)
H1A	0.6753	1.1296	0.4212	0.065*
N7	1.1303 (4)	1.0413 (3)	0.2394 (4)	0.0382 (8)
N8	1.1778 (6)	1.0723 (4)	0.3487 (6)	0.0664 (14)
N4	0.9978 (3)	0.6719 (3)	−0.1977 (4)	0.0371 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0276 (3)	0.0278 (3)	0.0339 (3)	−0.00349 (16)	0.0000 (2)	−0.00067 (16)
N5	0.0353 (18)	0.0345 (18)	0.0345 (18)	0.0002 (15)	0.0042 (15)	0.0007 (15)
N1	0.0323 (18)	0.039 (2)	0.041 (2)	0.0005 (15)	−0.0040 (16)	−0.0074 (16)
O1	0.0300 (15)	0.0434 (17)	0.0526 (19)	−0.0026 (13)	0.0022 (14)	−0.0189 (14)
C9	0.029 (2)	0.034 (2)	0.040 (2)	−0.0011 (16)	0.0015 (17)	0.0019 (17)
C8	0.032 (2)	0.049 (3)	0.053 (3)	0.011 (2)	0.005 (2)	0.006 (2)
C7	0.046 (3)	0.041 (2)	0.044 (2)	−0.004 (2)	0.003 (2)	−0.011 (2)
C6	0.028 (2)	0.036 (2)	0.034 (2)	−0.0015 (17)	0.0012 (17)	0.0041 (17)
C5	0.030 (3)	0.057 (3)	0.092 (5)	0.008 (2)	0.007 (3)	0.003 (3)
C4	0.036 (2)	0.044 (3)	0.061 (3)	−0.006 (2)	−0.005 (2)	0.004 (2)
C3	0.030 (2)	0.069 (4)	0.087 (4)	−0.005 (2)	−0.005 (3)	−0.001 (3)
C2	0.044 (3)	0.061 (3)	0.061 (3)	0.016 (2)	0.015 (2)	−0.012 (3)
C11	0.038 (2)	0.031 (2)	0.033 (2)	−0.0013 (17)	0.0002 (17)	−0.0049 (16)
N2	0.037 (2)	0.050 (2)	0.059 (3)	0.0069 (18)	−0.0083 (19)	−0.011 (2)
C10	0.039 (2)	0.0271 (19)	0.0290 (18)	−0.0014 (16)	−0.0001 (16)	−0.0019 (15)
N6	0.0348 (18)	0.0364 (19)	0.0341 (18)	−0.0118 (15)	−0.0039 (15)	0.0024 (14)
N3	0.036 (2)	0.054 (3)	0.061 (3)	0.0023 (18)	−0.0036 (19)	−0.019 (2)
C1	0.055 (3)	0.049 (3)	0.057 (3)	0.002 (2)	0.012 (3)	−0.017 (3)
N7	0.041 (2)	0.0360 (19)	0.0371 (19)	−0.0044 (16)	−0.0013 (16)	−0.0009 (15)
N8	0.089 (4)	0.062 (3)	0.048 (3)	−0.012 (3)	−0.018 (3)	−0.013 (2)
N4	0.0325 (18)	0.0384 (19)	0.0403 (19)	0.0055 (15)	−0.0001 (15)	−0.0099 (16)

Geometric parameters (Å, º) top

Zn1—N6	2.035 (4)	C5—C3	1.398 (9)
Zn1—N1	2.088 (4)	C5—H5A	0.930
Zn1—N4ⁱ	2.102 (4)	C4—C3	1.415 (7)
Zn1—N5	2.155 (4)	C4—H4A	0.930
Zn1—N6ⁱⁱ	2.291 (4)	C3—H3A	0.930
Zn1—O1	2.360 (4)	C2—C1	1.376 (8)
N5—C7	1.338 (6)	C2—H2A	0.930
N5—C6	1.373 (6)	C11—C10	1.522 (6)
N1—C10	1.318 (5)	C11—H11A	0.970
N1—N2	1.352 (5)	C11—H11B	0.970
O1—C9	1.371 (5)	N2—N3	1.302 (6)
O1—C11	1.428 (5)	C10—N4	1.318 (5)
C9—C4	1.366 (6)	N6—N7	1.199 (5)
C9—C6	1.426 (6)	N6—Zn1ⁱⁱ	2.291 (4)
C8—C2	1.401 (7)	N3—N4	1.361 (6)
C8—C5	1.410 (8)	C1—H1A	0.930
C8—C6	1.415 (6)	N7—N8	1.147 (6)
C7—C1	1.405 (7)	N4—Zn1ⁱⁱⁱ	2.102 (4)
C7—H7A	0.930

N6—Zn1—N1	113.67 (17)	C8—C6—C9	118.6 (4)
N6—Zn1—N4ⁱ	98.71 (15)	C3—C5—C8	120.9 (5)
N1—Zn1—N4ⁱ	91.07 (17)	C3—C5—H5A	119.5
N6—Zn1—N5	104.72 (17)	C8—C5—H5A	119.5
N1—Zn1—N5	140.15 (14)	C9—C4—C3	119.5 (5)
N4ⁱ—Zn1—N5	93.41 (15)	C9—C4—H4A	120.2
N6—Zn1—N6ⁱⁱ	78.59 (15)	C3—C4—H4A	120.2
N1—Zn1—N6ⁱⁱ	88.40 (17)	C5—C3—C4	119.9 (5)
N4ⁱ—Zn1—N6ⁱⁱ	176.76 (13)	C5—C3—H3A	120.1
N5—Zn1—N6ⁱⁱ	89.04 (15)	C4—C3—H3A	120.1
N6—Zn1—O1	162.00 (14)	C1—C2—C8	120.0 (5)
N1—Zn1—O1	69.91 (14)	C1—C2—H2A	120.0
N4ⁱ—Zn1—O1	98.84 (14)	C8—C2—H2A	120.0
N5—Zn1—O1	70.27 (15)	O1—C11—C10	103.0 (3)
N6ⁱⁱ—Zn1—O1	83.98 (13)	O1—C11—H11A	111.2
C7—N5—C6	117.7 (4)	C10—C11—H11A	111.2
C7—N5—Zn1	121.1 (3)	O1—C11—H11B	111.2
C6—N5—Zn1	121.1 (3)	C10—C11—H11B	111.2
C10—N1—N2	105.5 (4)	H11A—C11—H11B	109.1
C10—N1—Zn1	123.8 (3)	N3—N2—N1	108.4 (4)
N2—N1—Zn1	130.7 (3)	N4—C10—N1	112.2 (4)
C9—O1—C11	120.9 (3)	N4—C10—C11	125.7 (4)
C9—O1—Zn1	117.5 (3)	N1—C10—C11	122.1 (4)
C11—O1—Zn1	120.3 (2)	N7—N6—Zn1	127.4 (3)
C4—C9—O1	126.0 (4)	N7—N6—Zn1ⁱⁱ	125.3 (3)
C4—C9—C6	121.9 (4)	Zn1—N6—Zn1ⁱⁱ	101.41 (15)
O1—C9—C6	112.0 (4)	N2—N3—N4	109.7 (4)
C2—C8—C5	123.3 (5)	C2—C1—C7	119.0 (5)
C2—C8—C6	117.6 (5)	C2—C1—H1A	120.5
C5—C8—C6	119.1 (5)	C7—C1—H1A	120.5
N5—C7—C1	123.1 (5)	N8—N7—N6	177.4 (5)
N5—C7—H7A	118.4	C10—N4—N3	104.3 (4)
C1—C7—H7A	118.4	C10—N4—Zn1ⁱⁱⁱ	133.6 (3)
N5—C6—C8	122.5 (4)	N3—N4—Zn1ⁱⁱⁱ	117.0 (3)
N5—C6—C9	118.8 (4)

N6—Zn1—N5—C7	−19.6 (4)	C5—C8—C6—C9	−1.4 (7)
N1—Zn1—N5—C7	176.1 (3)	C4—C9—C6—N5	−179.8 (4)
N4ⁱ—Zn1—N5—C7	80.3 (4)	O1—C9—C6—N5	1.8 (6)
N6ⁱⁱ—Zn1—N5—C7	−97.6 (4)	C4—C9—C6—C8	2.3 (7)
O1—Zn1—N5—C7	178.5 (4)	O1—C9—C6—C8	−176.1 (4)
N6—Zn1—N5—C6	158.0 (3)	C2—C8—C5—C3	179.5 (5)
N1—Zn1—N5—C6	−6.3 (4)	C6—C8—C5—C3	0.4 (9)
N4ⁱ—Zn1—N5—C6	−102.1 (3)	O1—C9—C4—C3	176.1 (5)
N6ⁱⁱ—Zn1—N5—C6	80.0 (3)	C6—C9—C4—C3	−2.0 (7)
O1—Zn1—N5—C6	−3.9 (3)	C8—C5—C3—C4	−0.1 (10)
N6—Zn1—N1—C10	−154.1 (3)	C9—C4—C3—C5	0.9 (9)
N4ⁱ—Zn1—N1—C10	106.0 (4)	C5—C8—C2—C1	−180.0 (6)
N5—Zn1—N1—C10	9.3 (5)	C6—C8—C2—C1	−0.8 (8)
N6ⁱⁱ—Zn1—N1—C10	−77.3 (4)	C9—O1—C11—C10	176.3 (4)
O1—Zn1—N1—C10	6.9 (3)	Zn1—O1—C11—C10	9.5 (4)
N6—Zn1—N1—N2	23.8 (5)	C10—N1—N2—N3	1.5 (5)
N4ⁱ—Zn1—N1—N2	−76.2 (4)	Zn1—N1—N2—N3	−176.6 (3)
N5—Zn1—N1—N2	−172.8 (3)	N2—N1—C10—N4	−0.3 (5)
N6ⁱⁱ—Zn1—N1—N2	100.6 (4)	Zn1—N1—C10—N4	178.0 (3)
O1—Zn1—N1—N2	−175.2 (4)	N2—N1—C10—C11	177.4 (4)
N6—Zn1—O1—C9	−71.8 (5)	Zn1—N1—C10—C11	−4.3 (6)
N1—Zn1—O1—C9	−176.7 (3)	O1—C11—C10—N4	173.4 (4)
N4ⁱ—Zn1—O1—C9	95.4 (3)	O1—C11—C10—N1	−3.9 (5)
N5—Zn1—O1—C9	4.9 (3)	N1—Zn1—N6—N7	−123.2 (4)
N6ⁱⁱ—Zn1—O1—C9	−86.2 (3)	N4ⁱ—Zn1—N6—N7	−28.2 (4)
N6—Zn1—O1—C11	95.5 (5)	N5—Zn1—N6—N7	67.7 (4)
N1—Zn1—O1—C11	−9.5 (3)	N6ⁱⁱ—Zn1—N6—N7	153.7 (5)
N4ⁱ—Zn1—O1—C11	−97.4 (3)	O1—Zn1—N6—N7	139.0 (4)
N5—Zn1—O1—C11	172.1 (3)	N1—Zn1—N6—Zn1ⁱⁱ	83.13 (19)
N6ⁱⁱ—Zn1—O1—C11	81.0 (3)	N4ⁱ—Zn1—N6—Zn1ⁱⁱ	178.17 (15)
C11—O1—C9—C4	9.5 (7)	N5—Zn1—N6—Zn1ⁱⁱ	−85.94 (17)
Zn1—O1—C9—C4	176.6 (4)	N6ⁱⁱ—Zn1—N6—Zn1ⁱⁱ	0.0
C11—O1—C9—C6	−172.2 (4)	O1—Zn1—N6—Zn1ⁱⁱ	−14.7 (5)
Zn1—O1—C9—C6	−5.1 (5)	N1—N2—N3—N4	−2.1 (6)
C6—N5—C7—C1	1.2 (7)	C8—C2—C1—C7	0.3 (9)
Zn1—N5—C7—C1	178.9 (4)	N5—C7—C1—C2	−0.5 (9)
C7—N5—C6—C8	−1.8 (6)	N1—C10—N4—N3	−1.0 (5)
Zn1—N5—C6—C8	−179.4 (3)	C11—C10—N4—N3	−178.5 (4)
C7—N5—C6—C9	−179.6 (4)	N1—C10—N4—Zn1ⁱⁱⁱ	−153.6 (3)
Zn1—N5—C6—C9	2.8 (5)	C11—C10—N4—Zn1ⁱⁱⁱ	28.8 (7)
C2—C8—C6—N5	1.6 (7)	N2—N3—N4—C10	1.9 (5)
C5—C8—C6—N5	−179.2 (5)	N2—N3—N4—Zn1ⁱⁱⁱ	160.0 (3)
C2—C8—C6—C9	179.4 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···N2^iv	0.93	2.49	3.411 (8)	170
C11—H11B···N8^v	0.97	2.54	3.252 (7)	130

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₁H₈N₅O)(N₃)]
M_r	333.64
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	10.352 (8), 14.108 (9), 8.626 (8)
β (°)	90.31 (2)
V (Å³)	1259.8 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.96
Crystal size (mm)	0.18 × 0.12 × 0.10

Data collection
Diffractometer	Rigaku SCXmini CCD diffractometer
Absorption correction	Multi-scan CrystalClear (Rigaku, 2005)
T_min, T_max	0.714, 0.821
No. of measured, independent and observed [I > 2σ(I)] reflections	11540, 2714, 2261
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.183, 1.19
No. of reflections	2714
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.71

Computer programs: CrystalClear (Rigaku, 2005), 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
C3—H3A···N2ⁱ	0.93	2.49	3.411 (8)	169.8
C11—H11B···N8ⁱⁱ	0.97	2.54	3.252 (7)	129.9

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

Acknowledgements

This work was supported by a start-up grant from Southeast University.

References

Chen, F. & Ye, H.-Y. (2008). Acta Cryst. E64, m1060. Web of Science CSD CrossRef IUCr Journals Google Scholar
Luo, H.-Z. & Ye, H.-Y. (2008). Acta Cryst. E64, o136. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2005). 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
Wang, X.-S., Tang, Y.-Z., Huang, X.-F., Qu, Z.-R., Che, C.-M., Chan, C. W. H. & Xiong, R.-G. (2005). Inorg. Chem. 44, 5278–5285. Web of Science CSD CrossRef PubMed CAS Google Scholar
Wang, G.-X. & Ye, H.-Y. (2008). Acta Cryst. E64, m1006. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xiong, R.-G., Xue, X., Zhao, H., You, X.-Z., Abrahams, B. F. & Xue, Z.-L. (2002). Angew. Chem. Int. Ed. 41, 3800–3803. Web of Science CrossRef CAS 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.