catena-Poly[zinc(II)-bis-[μ-5-(2-amino-phenyl)tetra-zolato]-κN,N:N;κN:N,N].

The polymeric title compound, [Zn(C(7)H(6)N(5))(2)](n), was synthesized by the hydro-thermal reaction of Zn(NO(3))(2) with 2-amino-benzonitrile in the presence of NaN(3). The zinc(II) metal centre displays a distorted octa-hedral coordination environment provided by N atoms of two bidentate chelating and two monodentate 5-(2-amino-phen-yl)tetra-zolate ligands. These ligands act as bridges, linking adjacent Zn atoms into polymeric criss-crossed chains parallel to the [110] and [10] directions. Intra-chain N-H⋯N hydrogen-bonding inter-actions are observed.

Related literature

For the applications of tetra­zole compounds, see: Arp et al. (2000 ▶); Dunica et al. (1991 ▶); Wang et al. (2004 ▶, 2005 ▶); Wittenberger & Donner (1993 ▶).

Experimental

Crystal data

[Zn(C7H6N5)2]

M = 385.71

Monoclinic,

a = 10.6751 (16) Å

b = 10.9051 (14) Å

c = 25.321 (5) Å

β = 94.972 (13)°

V = 2936.6 (8) Å3

Z = 8

Mo Kα radiation

μ = 1.70 mm−1

T = 298 (2) K

0.28 × 0.12 × 0.10 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.783, T max = 0.844

14618 measured reflections

3343 independent reflections

2859 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.092

S = 1.09

3343 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.70 e Å−3

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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021946/rz2234sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021946/rz2234Isup2.hkl

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

[Zn(C7H6N5)2]	F000 = 1568
Mr = 385.71	Dx = 1.745 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3668 reflections
a = 10.6751 (16) Å	θ = 3.0–27.5º
b = 10.9051 (14) Å	µ = 1.70 mm−1
c = 25.321 (5) Å	T = 298 (2) K
β = 94.972 (13)º	Block, colourless
V = 2936.6 (8) Å3	0.28 × 0.12 × 0.10 mm
Z = 8

Rigaku Mercury2 diffractometer	3343 independent reflections
Radiation source: fine-focus sealed tube	2859 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.044
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 298(2) K	θmin = 3.0º
ω scans	h = −13→13
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −14→14
Tmin = 0.783, Tmax = 0.844	l = −32→32
14618 measured reflections

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0386P)2 + 3.3164P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
3343 reflections	Δρmax = 0.37 e Å−3
226 parameters	Δρmin = −0.70 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.16630 (3)	0.40663 (2)	0.032125 (11)	0.02512 (10)
N4	0.11712 (19)	0.60243 (17)	0.02478 (8)	0.0249 (4)
N10	0.0847 (2)	0.4084 (2)	0.10837 (9)	0.0323 (5)
H10A	0.0285	0.4696	0.1097	0.048*
H10B	0.0438	0.3365	0.1038	0.048*
C10	0.1638 (2)	0.4052 (2)	0.15692 (10)	0.0288 (5)
N9	0.3503 (2)	0.49221 (19)	0.04291 (9)	0.0310 (5)
H9A	0.4105	0.4343	0.0445	0.046*
H9B	0.3521	0.5348	0.0125	0.046*
C9	0.2582 (2)	0.3162 (2)	0.16320 (9)	0.0272 (5)
N8	0.24495 (18)	0.23775 (18)	0.06944 (8)	0.0245 (4)
C1	0.1781 (2)	0.6906 (2)	0.05410 (10)	0.0252 (5)
C2	0.2884 (2)	0.6711 (2)	0.09210 (10)	0.0283 (5)
C14	0.3353 (3)	0.3134 (3)	0.21067 (10)	0.0346 (6)
H14A	0.3983	0.2545	0.2154	0.041*
C3	0.3720 (2)	0.5736 (2)	0.08704 (11)	0.0291 (5)
C13	0.3197 (3)	0.3964 (3)	0.25076 (12)	0.0438 (7)
H13A	0.3718	0.3934	0.2821	0.053*
C4	0.4704 (3)	0.5554 (3)	0.12574 (13)	0.0404 (7)
H4A	0.5265	0.4913	0.1222	0.048*
C7	0.3079 (3)	0.7491 (3)	0.13564 (11)	0.0360 (6)
H7A	0.2553	0.8163	0.1385	0.043*
C6	0.4044 (3)	0.7281 (3)	0.17470 (12)	0.0437 (7)
H6A	0.4142	0.7788	0.2043	0.052*
C5	0.4859 (3)	0.6316 (3)	0.16940 (13)	0.0451 (7)
H5A	0.5515	0.6177	0.1953	0.054*
C11	0.1483 (3)	0.4882 (3)	0.19728 (12)	0.0414 (7)
H11A	0.0852	0.5470	0.1931	0.050*
C12	0.2265 (3)	0.4838 (3)	0.24397 (12)	0.0473 (8)
H12A	0.2160	0.5402	0.2708	0.057*
C8	0.2794 (2)	0.2265 (2)	0.12170 (9)	0.0250 (5)
N6	0.3457 (2)	0.0666 (2)	0.08495 (9)	0.0380 (6)
N5	0.3411 (2)	0.1218 (2)	0.13199 (9)	0.0368 (5)
N7	0.2890 (2)	0.13536 (19)	0.04763 (8)	0.0280 (4)
N1	0.1206 (2)	0.79890 (19)	0.04653 (9)	0.0330 (5)
N2	0.0204 (2)	0.77701 (19)	0.01204 (9)	0.0334 (5)
N3	0.01805 (19)	0.65985 (19)	−0.00074 (9)	0.0282 (5)

	U11	U22	U33	U12	U13	U23
Zn1	0.02992 (17)	0.02214 (16)	0.02306 (16)	0.00230 (11)	0.00100 (11)	0.00016 (11)
N4	0.0276 (10)	0.0202 (10)	0.0265 (10)	0.0028 (8)	0.0004 (8)	0.0011 (8)
N10	0.0334 (12)	0.0362 (12)	0.0277 (11)	0.0113 (9)	0.0041 (9)	0.0050 (9)
C10	0.0350 (14)	0.0262 (12)	0.0257 (12)	0.0023 (10)	0.0051 (10)	0.0031 (10)
N9	0.0311 (11)	0.0215 (10)	0.0408 (13)	0.0045 (9)	0.0056 (9)	0.0009 (9)
C9	0.0312 (13)	0.0276 (12)	0.0230 (12)	−0.0015 (10)	0.0028 (10)	0.0027 (10)
N8	0.0295 (10)	0.0217 (10)	0.0221 (10)	0.0045 (8)	0.0017 (8)	0.0006 (8)
C1	0.0270 (12)	0.0208 (11)	0.0284 (12)	0.0000 (9)	0.0056 (9)	0.0001 (10)
C2	0.0278 (12)	0.0253 (12)	0.0317 (13)	−0.0025 (10)	0.0016 (10)	0.0010 (10)
C14	0.0381 (15)	0.0354 (14)	0.0292 (13)	−0.0008 (12)	−0.0025 (11)	0.0022 (11)
C3	0.0292 (13)	0.0240 (12)	0.0343 (14)	−0.0020 (10)	0.0029 (10)	0.0024 (10)
C13	0.0549 (19)	0.0487 (18)	0.0266 (14)	−0.0089 (15)	−0.0029 (13)	−0.0062 (13)
C4	0.0330 (14)	0.0339 (14)	0.0528 (18)	0.0008 (12)	−0.0044 (13)	0.0080 (13)
C7	0.0381 (15)	0.0323 (14)	0.0371 (15)	−0.0016 (12)	0.0011 (12)	−0.0038 (12)
C6	0.0459 (17)	0.0455 (17)	0.0382 (16)	−0.0079 (14)	−0.0051 (13)	−0.0047 (14)
C5	0.0386 (16)	0.0472 (17)	0.0467 (18)	−0.0071 (14)	−0.0130 (13)	0.0094 (14)
C11	0.0539 (18)	0.0321 (14)	0.0396 (16)	0.0081 (13)	0.0128 (13)	−0.0022 (12)
C12	0.068 (2)	0.0427 (17)	0.0322 (15)	−0.0033 (16)	0.0106 (14)	−0.0131 (13)
C8	0.0256 (12)	0.0245 (12)	0.0248 (12)	0.0030 (10)	0.0019 (9)	0.0042 (10)
N6	0.0532 (15)	0.0346 (12)	0.0270 (12)	0.0154 (11)	0.0081 (10)	0.0042 (10)
N5	0.0485 (14)	0.0376 (12)	0.0245 (11)	0.0164 (11)	0.0034 (10)	0.0034 (10)
N7	0.0353 (11)	0.0245 (10)	0.0248 (11)	0.0062 (9)	0.0063 (9)	0.0007 (8)
N1	0.0308 (11)	0.0243 (11)	0.0426 (13)	0.0009 (9)	−0.0042 (10)	−0.0014 (10)
N2	0.0309 (11)	0.0233 (11)	0.0453 (14)	0.0024 (9)	−0.0012 (10)	0.0013 (10)
N3	0.0283 (11)	0.0243 (11)	0.0318 (11)	0.0027 (8)	0.0006 (9)	0.0029 (9)

Zn1—N7i	2.164 (2)	C2—C3	1.401 (4)
Zn1—N9	2.170 (2)	C14—C13	1.381 (4)
Zn1—N3ii	2.181 (2)	C14—H14A	0.9300
Zn1—N10	2.186 (2)	C3—C4	1.387 (4)
Zn1—N8	2.2027 (19)	C13—C12	1.377 (4)
Zn1—N4	2.2028 (19)	C13—H13A	0.9300
N4—N3	1.345 (3)	C4—C5	1.381 (5)
N4—C1	1.348 (3)	C4—H4A	0.9300
N10—C10	1.430 (3)	C7—C6	1.384 (4)
N10—H10A	0.9000	C7—H7A	0.9300
N10—H10B	0.9001	C6—C5	1.380 (4)
C10—C11	1.386 (4)	C6—H6A	0.9300
C10—C9	1.397 (3)	C5—H5A	0.9300
N9—C3	1.430 (3)	C11—C12	1.388 (4)
N9—H9A	0.9000	C11—H11A	0.9300
N9—H9B	0.9001	C12—H12A	0.9300
C9—C14	1.398 (3)	C8—N5	1.333 (3)
C9—C8	1.467 (3)	N6—N7	1.312 (3)
N8—C8	1.348 (3)	N6—N5	1.339 (3)
N8—N7	1.348 (3)	N7—Zn1i	2.164 (2)
C1—N1	1.337 (3)	N1—N2	1.342 (3)
C1—C2	1.470 (3)	N2—N3	1.318 (3)
C2—C7	1.394 (4)	N3—Zn1ii	2.181 (2)
N7i—Zn1—N9	86.46 (8)	C7—C2—C1	119.1 (2)
N7i—Zn1—N3ii	81.63 (8)	C3—C2—C1	122.0 (2)
N9—Zn1—N3ii	165.18 (8)	C13—C14—C9	121.2 (3)
N7i—Zn1—N10	164.38 (9)	C13—C14—H14A	119.4
N9—Zn1—N10	108.10 (9)	C9—C14—H14A	119.4
N3ii—Zn1—N10	84.76 (9)	C4—C3—C2	119.5 (3)
N7i—Zn1—N8	96.71 (7)	C4—C3—N9	121.7 (2)
N9—Zn1—N8	89.91 (8)	C2—C3—N9	118.8 (2)
N3ii—Zn1—N8	100.18 (8)	C12—C13—C14	119.6 (3)
N10—Zn1—N8	78.16 (8)	C12—C13—H13A	120.2
N7i—Zn1—N4	101.33 (8)	C14—C13—H13A	120.2
N9—Zn1—N4	78.48 (8)	C5—C4—C3	120.7 (3)
N3ii—Zn1—N4	95.19 (8)	C5—C4—H4A	119.6
N10—Zn1—N4	87.46 (8)	C3—C4—H4A	119.6
N8—Zn1—N4	157.80 (8)	C6—C7—C2	121.0 (3)
N3—N4—C1	104.77 (18)	C6—C7—H7A	119.5
N3—N4—Zn1	131.56 (16)	C2—C7—H7A	119.5
C1—N4—Zn1	123.01 (16)	C5—C6—C7	119.6 (3)
C10—N10—Zn1	120.53 (17)	C5—C6—H6A	120.2
C10—N10—H10A	109.5	C7—C6—H6A	120.2
Zn1—N10—H10A	110.9	C6—C5—C4	120.2 (3)
C10—N10—H10B	109.5	C6—C5—H5A	119.9
Zn1—N10—H10B	96.0	C4—C5—H5A	119.9
H10A—N10—H10B	109.5	C10—C11—C12	120.3 (3)
C11—C10—C9	120.0 (2)	C10—C11—H11A	119.9
C11—C10—N10	121.2 (2)	C12—C11—H11A	119.9
C9—C10—N10	118.8 (2)	C13—C12—C11	120.3 (3)
C3—N9—Zn1	116.66 (16)	C13—C12—H12A	119.8
C3—N9—H9A	109.5	C11—C12—H12A	119.8
Zn1—N9—H9A	109.8	N5—C8—N8	111.0 (2)
C3—N9—H9B	109.5	N5—C8—C9	122.4 (2)
Zn1—N9—H9B	101.6	N8—C8—C9	126.6 (2)
H9A—N9—H9B	109.5	N7—N6—N5	109.5 (2)
C10—C9—C14	118.6 (2)	C8—N5—N6	105.5 (2)
C10—C9—C8	122.4 (2)	N6—N7—N8	109.5 (2)
C14—C9—C8	119.0 (2)	N6—N7—Zn1i	115.23 (16)
C8—N8—N7	104.58 (19)	N8—N7—Zn1i	132.09 (16)
C8—N8—Zn1	123.94 (16)	C1—N1—N2	105.5 (2)
N7—N8—Zn1	130.57 (15)	N3—N2—N1	109.2 (2)
N1—C1—N4	110.9 (2)	N2—N3—N4	109.6 (2)
N1—C1—C2	123.6 (2)	N2—N3—Zn1ii	114.14 (16)
N4—C1—C2	125.4 (2)	N4—N3—Zn1ii	131.85 (16)
C7—C2—C3	118.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10A···N6iii	0.90	2.26	3.095 (3)	154
N9—H9A···N2iv	0.90	2.27	3.108 (3)	155
N9—H9B···N1v	0.90	2.38	3.246 (3)	160
N9—H9B···N2v	0.90	2.57	3.242 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10A⋯N6i	0.90	2.26	3.095 (3)	154
N9—H9A⋯N2ii	0.90	2.27	3.108 (3)	155
N9—H9B⋯N1iii	0.90	2.38	3.246 (3)	160
N9—H9B⋯N2iii	0.90	2.57	3.242 (3)	132

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