Bis[3-(pyrazin-2-yl)-5-(pyridin-2-yl-κN)-1,2,4-triazol-1-ido-κN(1)]copper(II).

In the mononuclear title complex, [Cu(C(11)H(7)N(6))(2)], the Cu(II) atom lies on a crystallographic inversion centre and is coordinated by four N atoms from two bidentate chelate monoanionic 3-(pyrazin-2-yl)-5-(pyridin-2-yl-1,2,4-triazol-1-ido ligands, two from the triazolide rings [Cu-N = 1.969 (2) Å] and two from the pyridine rings [Cu-N = 2.027 (2) Å], giving a slightly distorted square-planar geometry.

Related literature

For details of the synthesis and properties of related copper compounds showing a similar coordination environment, see: Meng et al. (2009 ▶); Cheng et al. (2007 ▶); Zhang et al. (2005 ▶). For the structure of an RuII complex with the same ligand, see: Browne et al. (2002 ▶).

Experimental

Crystal data

[Cu(C11H7N6)2]

M = 509.99

Monoclinic,

a = 11.9735 (4) Å

b = 10.7539 (3) Å

c = 8.0162 (3) Å

β = 106.500 (4)°

V = 989.67 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.15 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.795, T max = 0.795

3248 measured reflections

1739 independent reflections

1451 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.083

S = 1.06

1739 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016777/zs2193sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016777/zs2193Isup2.hkl

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

[Cu(C11H7N6)2]	F(000) = 518
Mr = 509.99	Dx = 1.711 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2919 reflections
a = 11.9735 (4) Å	θ = 2.6–25.0°
b = 10.7539 (3) Å	µ = 1.15 mm−1
c = 8.0162 (3) Å	T = 293 K
β = 106.500 (4)°	Block, black
V = 989.67 (6) Å3	0.20 × 0.20 × 0.20 mm
Z = 2

Bruker SMART APEX I diffractometer	1739 independent reflections
Radiation source: fine-focus sealed tube	1451 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.192 pixels mm-1	θmax = 25.0°, θmin = 2.6°
ω–2θ scans	h = −14→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→12
Tmin = 0.795, Tmax = 0.795	l = −9→6
3248 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0356P)2 + 0.5521P] where P = (Fo2 + 2Fc2)/3
1739 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
Cu1	1.00000	1.00000	0.00000	0.0286 (2)
N1	1.10513 (18)	0.85051 (18)	0.0123 (3)	0.0267 (7)
N2	0.91236 (19)	0.87911 (18)	0.0980 (3)	0.0288 (7)
N3	0.81241 (19)	0.87336 (18)	0.1478 (3)	0.0298 (7)
N4	0.88670 (18)	0.67872 (18)	0.1531 (3)	0.0282 (7)
N5	0.6786 (2)	0.5834 (2)	0.2120 (3)	0.0376 (8)
N6	0.5319 (2)	0.7455 (2)	0.3250 (3)	0.0398 (8)
C1	1.0605 (2)	0.7434 (2)	0.0551 (3)	0.0250 (8)
C2	1.1125 (2)	0.6297 (2)	0.0511 (3)	0.0319 (8)
C3	1.2139 (2)	0.6250 (2)	0.0029 (4)	0.0344 (9)
C4	1.2622 (2)	0.7337 (2)	−0.0353 (4)	0.0355 (9)
C5	1.2058 (2)	0.8444 (2)	−0.0294 (3)	0.0307 (8)
C6	0.9528 (2)	0.7623 (2)	0.1032 (3)	0.0257 (8)
C7	0.8009 (2)	0.7528 (2)	0.1784 (3)	0.0262 (8)
C8	0.6998 (2)	0.7053 (2)	0.2278 (3)	0.0258 (8)
C9	0.6261 (2)	0.7845 (2)	0.2850 (4)	0.0328 (9)
C10	0.5123 (3)	0.6236 (3)	0.3091 (4)	0.0420 (10)
C11	0.5841 (3)	0.5442 (3)	0.2539 (4)	0.0446 (10)
H2	1.07980	0.55750	0.08060	0.0380*
H3	1.24950	0.54900	−0.00390	0.0410*
H4	1.33200	0.73230	−0.06470	0.0430*
H5	1.23870	0.91770	−0.05530	0.0370*
H9	0.64390	0.86880	0.29570	0.0390*
H10	0.44770	0.59120	0.33650	0.0500*
H11	0.56640	0.45980	0.24520	0.0530*

	U11	U22	U33	U12	U13	U23
Cu1	0.0274 (3)	0.0210 (2)	0.0417 (3)	0.0025 (2)	0.0166 (2)	0.0069 (2)
N1	0.0255 (11)	0.0248 (11)	0.0306 (12)	−0.0007 (9)	0.0092 (9)	0.0017 (9)
N2	0.0296 (12)	0.0218 (11)	0.0384 (13)	0.0016 (9)	0.0150 (10)	0.0034 (9)
N3	0.0308 (12)	0.0241 (11)	0.0392 (13)	−0.0009 (10)	0.0174 (10)	0.0027 (10)
N4	0.0278 (12)	0.0226 (11)	0.0364 (13)	−0.0014 (9)	0.0127 (10)	0.0008 (9)
N5	0.0386 (14)	0.0235 (11)	0.0580 (16)	−0.0004 (11)	0.0257 (12)	−0.0021 (11)
N6	0.0340 (14)	0.0332 (13)	0.0579 (16)	0.0034 (11)	0.0222 (12)	−0.0018 (11)
C1	0.0237 (13)	0.0249 (13)	0.0252 (13)	−0.0014 (11)	0.0051 (11)	0.0005 (11)
C2	0.0345 (15)	0.0234 (13)	0.0378 (15)	−0.0019 (12)	0.0104 (12)	−0.0004 (11)
C3	0.0341 (16)	0.0282 (14)	0.0429 (16)	0.0073 (12)	0.0142 (13)	−0.0013 (12)
C4	0.0304 (15)	0.0365 (15)	0.0433 (17)	0.0050 (13)	0.0166 (14)	0.0024 (13)
C5	0.0262 (14)	0.0270 (14)	0.0408 (16)	−0.0008 (11)	0.0127 (12)	0.0046 (12)
C6	0.0269 (14)	0.0204 (13)	0.0301 (15)	−0.0008 (11)	0.0085 (12)	0.0019 (10)
C7	0.0287 (14)	0.0231 (12)	0.0282 (14)	−0.0015 (11)	0.0106 (12)	−0.0003 (10)
C8	0.0279 (14)	0.0226 (13)	0.0279 (14)	−0.0006 (11)	0.0097 (11)	0.0022 (11)
C9	0.0350 (16)	0.0233 (13)	0.0428 (16)	−0.0003 (12)	0.0156 (13)	−0.0003 (12)
C10	0.0337 (16)	0.0381 (16)	0.060 (2)	−0.0052 (13)	0.0225 (15)	0.0020 (14)
C11	0.0429 (18)	0.0256 (14)	0.073 (2)	−0.0053 (13)	0.0291 (17)	0.0016 (14)

Cu1—N1	2.027 (2)	C1—C2	1.377 (3)
Cu1—N2	1.969 (2)	C1—C6	1.461 (3)
Cu1—N1i	2.027 (2)	C2—C3	1.376 (4)
Cu1—N2i	1.969 (2)	C3—C4	1.377 (3)
N1—C1	1.354 (3)	C4—C5	1.376 (3)
N1—C5	1.341 (3)	C7—C8	1.468 (3)
N2—N3	1.366 (3)	C8—C9	1.394 (3)
N2—C6	1.343 (3)	C10—C11	1.371 (5)
N3—C7	1.334 (3)	C2—H2	0.9300
N4—C6	1.332 (3)	C3—H3	0.9300
N4—C7	1.360 (3)	C4—H4	0.9300
N5—C8	1.334 (3)	C5—H5	0.9300
N5—C11	1.337 (4)	C9—H9	0.9300
N6—C9	1.325 (4)	C10—H10	0.9300
N6—C10	1.332 (4)	C11—H11	0.9300
N1—Cu1—N2	81.43 (9)	N4—C6—C1	129.0 (2)
N1—Cu1—N1i	180.00	N3—C7—N4	114.8 (2)
N1—Cu1—N2i	98.58 (9)	N3—C7—C8	121.6 (2)
N1i—Cu1—N2	98.58 (9)	N4—C7—C8	123.5 (2)
N2—Cu1—N2i	180.00	N5—C8—C7	117.7 (2)
N1i—Cu1—N2i	81.43 (9)	N5—C8—C9	120.7 (2)
Cu1—N1—C1	113.74 (17)	C7—C8—C9	121.6 (2)
Cu1—N1—C5	128.07 (16)	N6—C9—C8	123.2 (2)
C1—N1—C5	118.0 (2)	N6—C10—C11	122.3 (3)
Cu1—N2—N3	139.18 (16)	N5—C11—C10	122.5 (3)
Cu1—N2—C6	113.69 (18)	C1—C2—H2	121.00
N3—N2—C6	106.66 (19)	C3—C2—H2	121.00
N2—N3—C7	104.0 (2)	C2—C3—H3	120.00
C6—N4—C7	100.83 (19)	C4—C3—H3	120.00
C8—N5—C11	116.0 (2)	C3—C4—H4	120.00
C9—N6—C10	115.3 (3)	C5—C4—H4	120.00
N1—C1—C2	122.4 (2)	N1—C5—H5	119.00
N1—C1—C6	112.9 (2)	C4—C5—H5	119.00
C2—C1—C6	124.7 (2)	N6—C9—H9	118.00
C1—C2—C3	118.7 (2)	C8—C9—H9	118.00
C2—C3—C4	119.4 (2)	N6—C10—H10	119.00
C3—C4—C5	119.1 (2)	C11—C10—H10	119.00
N1—C5—C4	122.4 (2)	N5—C11—H11	119.00
N2—C6—N4	113.6 (2)	C10—C11—H11	119.00
N2—C6—C1	117.4 (2)
N2—Cu1—N1—C1	8.16 (18)	C7—N4—C6—N2	0.2 (3)
N2i—Cu1—N1—C1	−171.84 (18)	C6—N4—C7—C8	177.0 (2)
N2—Cu1—N1—C5	−177.6 (2)	C8—N5—C11—C10	0.3 (4)
N2i—Cu1—N1—C5	2.4 (2)	C11—N5—C8—C7	−178.3 (2)
N1—Cu1—N2—N3	−178.5 (3)	C11—N5—C8—C9	0.0 (4)
N1i—Cu1—N2—N3	1.5 (3)	C9—N6—C10—C11	−0.5 (4)
N1—Cu1—N2—C6	−7.77 (18)	C10—N6—C9—C8	0.8 (4)
N1i—Cu1—N2—C6	172.23 (18)	N1—C1—C6—N2	0.5 (3)
Cu1—N1—C5—C4	−172.0 (2)	N1—C1—C2—C3	0.4 (4)
C1—N1—C5—C4	2.1 (4)	C2—C1—C6—N4	1.1 (4)
Cu1—N1—C1—C2	172.57 (18)	C2—C1—C6—N2	−179.0 (2)
C5—N1—C1—C2	−2.3 (4)	N1—C1—C6—N4	−179.5 (2)
Cu1—N1—C1—C6	−6.9 (3)	C6—C1—C2—C3	179.8 (2)
C5—N1—C1—C6	178.2 (2)	C1—C2—C3—C4	1.7 (4)
N3—N2—C6—C1	−179.9 (2)	C2—C3—C4—C5	−2.0 (4)
Cu1—N2—C6—N4	−173.66 (17)	C3—C4—C5—N1	0.0 (4)
Cu1—N2—N3—C7	170.9 (2)	N3—C7—C8—N5	162.8 (2)
C6—N2—N3—C7	−0.2 (3)	N4—C7—C8—C9	167.4 (2)
N3—N2—C6—N4	0.0 (3)	N4—C7—C8—N5	−14.3 (4)
Cu1—N2—C6—C1	6.4 (3)	N3—C7—C8—C9	−15.5 (4)
N2—N3—C7—C8	−177.0 (2)	C7—C8—C9—N6	177.6 (2)
N2—N3—C7—N4	0.3 (3)	N5—C8—C9—N6	−0.6 (4)
C7—N4—C6—C1	−179.9 (2)	N6—C10—C11—N5	−0.1 (5)
C6—N4—C7—N3	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N5ii	0.93	2.52	3.303 (3)	141
C5—H5···N3i	0.93	2.39	3.169 (3)	141