Dichlorido(2,6-dipyrazol-1-ylpyridine)zinc(II).

In the title complex, [ZnCl(2)(C(11)H(9)N(5))], the Zn(II) ion assumes a distorted trigonal-bipyramidal ZnN(3)Cl(2) coordination geometry [Zn-N = 2.1397 (16)-2.2117 (17) Å, Zn-Cl = 2.2470 (6) and 2.2564 (6) Å]. The crystal packing exhibits π-π stacking inter-actions between the 2,6-dipyrazol-1-ylpyridine ligands of neighbouring mol-ecules.

Related literature

For the related crystal structure of dichlorido­[2,6-bis(pyrazol­yl­meth­yl)pyridine]zinc(II), see Balamurugan et al. (2004 ▶).

Experimental

Crystal data

[ZnCl2(C11H9N5)]

M = 347.50

Monoclinic,

a = 10.9630 (17) Å

b = 8.0263 (13) Å

c = 14.943 (2) Å

β = 93.079 (2)°

V = 1313.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.27 mm−1

T = 298 (2) K

0.48 × 0.42 × 0.29 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.409, T max = 0.559 (expected range = 0.379–0.518)

7375 measured reflections

2848 independent reflections

2431 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.078

S = 1.05

2848 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031152/cv2454sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031152/cv2454Isup2.hkl

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

[ZnCl2(C11H9N5)]	F(000) = 696
Mr = 347.50	Dx = 1.758 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3889 reflections
a = 10.9630 (17) Å	θ = 2.4–28.2°
b = 8.0263 (13) Å	µ = 2.27 mm−1
c = 14.943 (2) Å	T = 298 K
β = 93.079 (2)°	Block, colourless
V = 1313.0 (4) Å3	0.48 × 0.42 × 0.29 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2848 independent reflections
Radiation source: fine-focus sealed tube	2431 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→14
Tmin = 0.409, Tmax = 0.559	k = −9→10
7375 measured reflections	l = −16→18

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0445P)2 + 0.0869P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
2848 reflections	Δρmax = 0.28 e Å−3
173 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0167 (11)

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
C1	0.47097 (18)	0.3058 (2)	0.04770 (16)	0.0447 (5)
H1	0.4465	0.3525	0.1008	0.054*
C2	0.40961 (19)	0.3275 (3)	−0.03549 (17)	0.0478 (5)
H2	0.3389	0.3891	−0.0481	0.057*
C3	0.47479 (18)	0.2396 (2)	−0.09475 (16)	0.0440 (5)
H3	0.4572	0.2292	−0.1561	0.053*
C4	0.66172 (17)	0.0609 (2)	−0.07399 (13)	0.0349 (4)
C5	0.66885 (19)	0.0026 (3)	−0.16015 (14)	0.0448 (5)
H5	0.6147	0.0387	−0.2062	0.054*
C6	0.7591 (2)	−0.1111 (3)	−0.17553 (16)	0.0487 (5)
H6	0.7663	−0.1533	−0.2330	0.058*
C7	0.8394 (2)	−0.1637 (3)	−0.10659 (15)	0.0442 (5)
H7	0.8998	−0.2423	−0.1160	0.053*
C8	0.82578 (17)	−0.0944 (2)	−0.02369 (14)	0.0357 (4)
C9	0.99689 (18)	−0.2410 (2)	0.06325 (16)	0.0454 (5)
H9	1.0275	−0.3088	0.0192	0.054*
C10	1.0387 (2)	−0.2314 (3)	0.14943 (17)	0.0502 (6)
H10	1.1036	−0.2903	0.1767	0.060*
C11	0.9647 (2)	−0.1152 (3)	0.18931 (17)	0.0491 (6)
H11	0.9730	−0.0837	0.2492	0.059*
Cl1	0.65199 (5)	0.06053 (7)	0.25184 (4)	0.05045 (17)
Cl2	0.83525 (5)	0.37392 (6)	0.12155 (4)	0.04545 (15)
N1	0.74008 (13)	0.01621 (18)	−0.00710 (10)	0.0327 (3)
N2	0.90163 (15)	−0.13336 (19)	0.05243 (12)	0.0374 (4)
N3	0.88095 (15)	−0.0554 (2)	0.13084 (11)	0.0417 (4)
N4	0.57069 (14)	0.1699 (2)	−0.04655 (11)	0.0366 (4)
N5	0.56823 (14)	0.2105 (2)	0.04169 (11)	0.0385 (4)
Zn1	0.73202 (2)	0.13073 (3)	0.121755 (15)	0.03696 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0377 (11)	0.0347 (10)	0.0624 (14)	−0.0040 (8)	0.0090 (10)	−0.0009 (10)
C2	0.0347 (10)	0.0363 (10)	0.0721 (16)	−0.0005 (9)	−0.0004 (10)	0.0102 (10)
C3	0.0360 (10)	0.0439 (11)	0.0512 (13)	−0.0045 (9)	−0.0066 (9)	0.0124 (9)
C4	0.0329 (10)	0.0332 (9)	0.0386 (11)	−0.0072 (7)	0.0014 (8)	0.0020 (8)
C5	0.0441 (11)	0.0538 (12)	0.0361 (11)	−0.0052 (10)	−0.0025 (9)	0.0023 (9)
C6	0.0539 (13)	0.0570 (13)	0.0357 (12)	−0.0052 (10)	0.0062 (10)	−0.0076 (10)
C7	0.0428 (12)	0.0470 (11)	0.0435 (12)	0.0032 (9)	0.0071 (9)	−0.0029 (9)
C8	0.0338 (10)	0.0337 (9)	0.0400 (11)	−0.0062 (8)	0.0054 (8)	0.0026 (8)
C9	0.0392 (11)	0.0374 (11)	0.0599 (15)	0.0031 (9)	0.0064 (10)	0.0053 (9)
C10	0.0414 (11)	0.0469 (12)	0.0613 (15)	0.0030 (9)	−0.0047 (10)	0.0154 (11)
C11	0.0458 (12)	0.0549 (13)	0.0460 (14)	0.0010 (10)	−0.0036 (10)	0.0090 (10)
Cl1	0.0523 (3)	0.0611 (4)	0.0389 (3)	−0.0069 (2)	0.0112 (2)	−0.0012 (2)
Cl2	0.0431 (3)	0.0428 (3)	0.0500 (3)	−0.0086 (2)	−0.0017 (2)	−0.0035 (2)
N1	0.0309 (8)	0.0332 (8)	0.0338 (9)	−0.0042 (6)	0.0000 (7)	0.0014 (7)
N2	0.0348 (9)	0.0376 (9)	0.0400 (10)	0.0006 (6)	0.0034 (7)	0.0025 (7)
N3	0.0413 (9)	0.0486 (10)	0.0351 (9)	0.0030 (8)	0.0022 (7)	0.0011 (7)
N4	0.0316 (8)	0.0370 (8)	0.0407 (10)	−0.0038 (7)	−0.0015 (7)	0.0037 (7)
N5	0.0359 (9)	0.0376 (9)	0.0419 (10)	−0.0029 (7)	0.0022 (7)	−0.0007 (7)
Zn1	0.03632 (16)	0.04045 (17)	0.03418 (17)	−0.00377 (9)	0.00263 (10)	−0.00260 (9)

C1—N5	1.319 (3)	C8—N1	1.325 (2)
C1—C2	1.392 (3)	C8—N2	1.408 (3)
C1—H1	0.9300	C9—C10	1.346 (3)
C2—C3	1.364 (3)	C9—N2	1.358 (2)
C2—H2	0.9300	C9—H9	0.9300
C3—N4	1.362 (2)	C10—C11	1.391 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—N1	1.332 (2)	C11—N3	1.323 (3)
C4—C5	1.376 (3)	C11—H11	0.9300
C4—N4	1.405 (2)	Cl1—Zn1	2.2470 (6)
C5—C6	1.374 (3)	Cl2—Zn1	2.2564 (6)
C5—H5	0.9300	N1—Zn1	2.1397 (16)
C6—C7	1.385 (3)	N2—N3	1.358 (2)
C6—H6	0.9300	N3—Zn1	2.2117 (17)
C7—C8	1.374 (3)	N4—N5	1.360 (2)
C7—H7	0.9300	N5—Zn1	2.1988 (16)
Cg1···Cg2i	3.4087 (12)	Cg2···Cg3i	3.6253 (13)
N5—C1—C2	111.4 (2)	C11—C10—H10	127.1
N5—C1—H1	124.3	N3—C11—C10	111.1 (2)
C2—C1—H1	124.3	N3—C11—H11	124.4
C3—C2—C1	105.67 (19)	C10—C11—H11	124.4
C3—C2—H2	127.2	C8—N1—C4	118.37 (17)
C1—C2—H2	127.2	C8—N1—Zn1	121.33 (13)
N4—C3—C2	106.6 (2)	C4—N1—Zn1	120.23 (13)
N4—C3—H3	126.7	C9—N2—N3	110.69 (17)
C2—C3—H3	126.7	C9—N2—C8	130.90 (18)
N1—C4—C5	122.93 (18)	N3—N2—C8	118.41 (16)
N1—C4—N4	112.86 (17)	C11—N3—N2	105.09 (18)
C5—C4—N4	124.19 (18)	C11—N3—Zn1	140.30 (16)
C6—C5—C4	117.4 (2)	N2—N3—Zn1	114.53 (12)
C6—C5—H5	121.3	N5—N4—C3	111.07 (17)
C4—C5—H5	121.3	N5—N4—C4	118.92 (16)
C5—C6—C7	120.8 (2)	C3—N4—C4	129.90 (18)
C5—C6—H6	119.6	C1—N5—N4	105.25 (17)
C7—C6—H6	119.6	C1—N5—Zn1	140.46 (15)
C8—C7—C6	116.84 (19)	N4—N5—Zn1	113.56 (11)
C8—C7—H7	121.6	N1—Zn1—N5	72.99 (6)
C6—C7—H7	121.6	N1—Zn1—N3	72.49 (6)
N1—C8—C7	123.55 (19)	N5—Zn1—N3	143.97 (6)
N1—C8—N2	113.06 (17)	N1—Zn1—Cl1	135.05 (4)
C7—C8—N2	123.38 (18)	N5—Zn1—Cl1	101.44 (5)
C10—C9—N2	107.3 (2)	N3—Zn1—Cl1	95.67 (5)
C10—C9—H9	126.3	N1—Zn1—Cl2	108.99 (4)
N2—C9—H9	126.3	N5—Zn1—Cl2	98.18 (5)
C9—C10—C11	105.8 (2)	N3—Zn1—Cl2	102.45 (5)
C9—C10—H10	127.1	Cl1—Zn1—Cl2	115.93 (2)
N5—C1—C2—C3	−0.1 (2)	C5—C4—N4—N5	175.69 (18)
C1—C2—C3—N4	−0.1 (2)	N1—C4—N4—C3	−178.85 (18)
N1—C4—C5—C6	2.3 (3)	C5—C4—N4—C3	−0.2 (3)
N4—C4—C5—C6	−176.27 (18)	C2—C1—N5—N4	0.2 (2)
C4—C5—C6—C7	−0.2 (3)	C2—C1—N5—Zn1	169.07 (15)
C5—C6—C7—C8	−1.3 (3)	C3—N4—N5—C1	−0.3 (2)
C6—C7—C8—N1	0.9 (3)	C4—N4—N5—C1	−176.86 (16)
C6—C7—C8—N2	−178.97 (18)	C3—N4—N5—Zn1	−172.54 (12)
N2—C9—C10—C11	0.3 (2)	C4—N4—N5—Zn1	10.85 (19)
C9—C10—C11—N3	0.0 (3)	C8—N1—Zn1—N5	−173.52 (14)
C7—C8—N1—C4	1.0 (3)	C4—N1—Zn1—N5	9.64 (13)
N2—C8—N1—C4	−179.07 (15)	C8—N1—Zn1—N3	−4.01 (13)
C7—C8—N1—Zn1	−175.88 (15)	C4—N1—Zn1—N3	179.15 (15)
N2—C8—N1—Zn1	4.0 (2)	C8—N1—Zn1—Cl1	−84.26 (14)
C5—C4—N1—C8	−2.7 (3)	C4—N1—Zn1—Cl1	98.90 (13)
N4—C4—N1—C8	176.00 (15)	C8—N1—Zn1—Cl2	93.49 (13)
C5—C4—N1—Zn1	174.24 (14)	C4—N1—Zn1—Cl2	−83.35 (13)
N4—C4—N1—Zn1	−7.1 (2)	C1—N5—Zn1—N1	−178.6 (2)
C10—C9—N2—N3	−0.4 (2)	N4—N5—Zn1—N1	−10.30 (11)
C10—C9—N2—C8	179.88 (19)	C1—N5—Zn1—N3	164.27 (19)
N1—C8—N2—C9	178.77 (18)	N4—N5—Zn1—N3	−27.46 (18)
C7—C8—N2—C9	−1.3 (3)	C1—N5—Zn1—Cl1	47.6 (2)
N1—C8—N2—N3	−0.9 (2)	N4—N5—Zn1—Cl1	−144.18 (11)
C7—C8—N2—N3	179.04 (18)	C1—N5—Zn1—Cl2	−71.1 (2)
C10—C11—N3—N2	−0.3 (2)	N4—N5—Zn1—Cl2	97.15 (12)
C10—C11—N3—Zn1	−176.68 (16)	C11—N3—Zn1—N1	179.3 (2)
C9—N2—N3—C11	0.4 (2)	N2—N3—Zn1—N1	3.17 (12)
C8—N2—N3—C11	−179.84 (17)	C11—N3—Zn1—N5	−163.4 (2)
C9—N2—N3—Zn1	177.92 (12)	N2—N3—Zn1—N5	20.38 (19)
C8—N2—N3—Zn1	−2.4 (2)	C11—N3—Zn1—Cl1	−45.1 (2)
C2—C3—N4—N5	0.2 (2)	N2—N3—Zn1—Cl1	138.76 (12)
C2—C3—N4—C4	176.33 (18)	C11—N3—Zn1—Cl2	73.1 (2)
N1—C4—N4—N5	−3.0 (2)	N2—N3—Zn1—Cl2	−103.08 (12)

Table 1

Selected interatomic distances (Å)

Cg1, Cg2 and Cg3 are the centroids of the C4/N1/N4/N5/Zn1, C1–C3/N4/N5 and C4–C8/N1 rings, respectively.

Cg1⋯Cg2i	3.4087 (12)
Cg2⋯Cg3i	3.6253 (13)

Symmetry code: (i) .