Tetra-kis(dimethyl-ammonium) trans-di-chloridobis[5,5'-(pyrazine-2,3-diyl)bis(1H-tetra-zol-1-ido-κN(1))]copper(II).

The title compound, (C(2)H(8)N)(4)[Cu(C(6)H(2)N(10))(2)Cl(2)], consists of an anionic complex which is composed of a Cu(II) ion surrounded by four N atoms from two pyrazine-2,3-diylbis(1H-tetra-zol-1-ide) ligands, and two Cl(-) atoms in a trans-Cl(2)N(4) coordination geometry; the Cu(II) atom lies on a site of symmetry 2/m. The Cu-Cl distance of 2.8719 (5) Å is long due to the Jahn-Teller distortion of the d(9) electron configuration of Cu(II) ion. The tetra-zole and pyrazine rings make an N-C-C-N torsion angle of 38.25 (17)°. The charge of the anionic complex is balanced by four dimethyl-ammonium cations, which inter-act with the anionic complexes via N-H⋯N and N-H⋯Cl hydrogen bonds.

Related literature

For the coordination compound of 2,3-di-1H-tetra­zol-5-yl­pyrazine, see: Li et al. (2008 ▶). For related structure, see Tao et al. (2010 ▶).

Experimental

Crystal data

(C2H8N)4[n class="Chemical">Cu(C6H2N10)2Cl2]

M = 747.17

Orthorhombic,

a = 20.613 (2) Å

b = 10.5671 (9) Å

c = 15.0687 (12) Å

V = 3282.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.89 mm−1

T = 293 K

0.06 × 0.06 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.947, T max = 0.959

18389 measured reflections

2079 independent reflections

1888 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.085

S = 1.08

2079 reflections

120 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.74 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036896/pk2440sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812036896/pk2440Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036896/pk2440Isup3.hkl

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

(C2H8N)4[Cu(C6H2N10)2Cl2]	F(000) = 1548
Mr = 747.17	Dx = 1.512 Mg m−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 999 reflections
a = 20.613 (2) Å	θ = 5–23.5°
b = 10.5671 (9) Å	µ = 0.89 mm−1
c = 15.0687 (12) Å	T = 293 K
V = 3282.3 (5) Å3	Hexagonal, blue
Z = 4	0.06 × 0.06 × 0.05 mm

Bruker SMART APEX diffractometer	2079 independent reflections
Radiation source: fine-focus sealed tube	1888 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ–ω scan	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −27→26
Tmin = 0.947, Tmax = 0.959	k = −14→14
18389 measured reflections	l = −19→20

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0517P)2 + 1.6198P] where P = (Fo2 + 2Fc2)/3
2079 reflections	(Δ/σ)max = 0.001
120 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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
Cu1	0.5000	0.0000	0.5000	0.02900 (12)
Cl1	0.5000	−0.23652 (5)	0.59389 (3)	0.03605 (14)
C1	0.42546 (6)	0.07284 (12)	0.66989 (8)	0.0248 (3)
C2	0.46598 (6)	0.00989 (11)	0.73673 (8)	0.0253 (3)
C3	0.46657 (8)	−0.09929 (14)	0.86700 (10)	0.0391 (3)
H3	0.4447	−0.1387	0.9134	0.047*
C4	0.32397 (9)	0.36802 (17)	0.42405 (12)	0.0474 (4)
H4A	0.3170	0.3341	0.4824	0.071*
H4B	0.2836	0.3985	0.4006	0.071*
H4C	0.3545	0.4366	0.4273	0.071*
C5	0.30596 (8)	0.15966 (16)	0.35528 (11)	0.0442 (4)
H5A	0.3052	0.1116	0.4093	0.066*
H5B	0.3210	0.1070	0.3076	0.066*
H5C	0.2630	0.1894	0.3421	0.066*
N1	0.43237 (5)	0.07041 (10)	0.58166 (7)	0.0266 (2)
N2	0.38148 (6)	0.13511 (11)	0.54897 (7)	0.0323 (3)
N3	0.34593 (6)	0.17510 (12)	0.61510 (8)	0.0342 (3)
N4	0.37226 (6)	0.13670 (11)	0.69221 (8)	0.0312 (3)
N5	0.43235 (6)	−0.04459 (12)	0.80258 (8)	0.0349 (3)
N6	0.34981 (6)	0.26828 (14)	0.36567 (9)	0.0364 (3)
H6A	0.3595 (11)	0.3006 (19)	0.3099 (15)	0.059 (6)*
H6B	0.3887 (12)	0.2447 (19)	0.3834 (13)	0.053 (6)*

	U11	U22	U33	U12	U13	U23
Cu1	0.01762 (17)	0.0475 (2)	0.02182 (18)	0.000	0.000	−0.01293 (12)
Cl1	0.0268 (2)	0.0411 (3)	0.0402 (3)	0.000	0.000	0.0032 (2)
C1	0.0213 (6)	0.0300 (6)	0.0231 (6)	−0.0018 (4)	0.0021 (4)	−0.0041 (5)
C2	0.0256 (7)	0.0273 (6)	0.0231 (6)	−0.0004 (5)	0.0013 (5)	−0.0038 (4)
C3	0.0442 (8)	0.0416 (8)	0.0316 (7)	−0.0034 (7)	0.0052 (6)	0.0105 (6)
C4	0.0503 (10)	0.0485 (9)	0.0433 (9)	0.0003 (7)	0.0054 (8)	0.0000 (7)
C5	0.0405 (8)	0.0494 (9)	0.0428 (8)	0.0033 (7)	−0.0050 (7)	−0.0014 (7)
N1	0.0206 (5)	0.0374 (6)	0.0219 (5)	0.0022 (4)	−0.0014 (4)	−0.0042 (4)
N2	0.0238 (5)	0.0458 (7)	0.0274 (6)	0.0061 (5)	−0.0025 (4)	−0.0016 (5)
N3	0.0257 (6)	0.0451 (7)	0.0319 (6)	0.0078 (5)	0.0006 (4)	−0.0013 (5)
N4	0.0270 (6)	0.0386 (6)	0.0279 (5)	0.0055 (4)	0.0045 (4)	−0.0020 (5)
N5	0.0324 (6)	0.0413 (6)	0.0309 (6)	−0.0036 (5)	0.0041 (5)	0.0050 (5)
N6	0.0244 (6)	0.0565 (8)	0.0282 (6)	0.0034 (5)	0.0017 (5)	0.0067 (5)

Cu1—N1i	2.0029 (10)	C4—H4A	0.9600
Cu1—N1ii	2.0029 (10)	C4—H4B	0.9600
Cu1—N1	2.0029 (10)	C4—H4C	0.9600
Cu1—N1iii	2.0029 (10)	C5—N6	1.469 (2)
Cu1—Cl1	2.8719 (5)	C5—H5A	0.9600
C1—N4	1.3309 (16)	C5—H5B	0.9600
C1—N1	1.3374 (15)	C5—H5C	0.9600
C1—C2	1.4678 (17)	N1—N2	1.3455 (15)
C2—N5	1.3405 (17)	N1—N2	1.3455 (15)
C2—C2ii	1.402 (3)	N2—N3	1.3071 (16)
C3—N5	1.3319 (19)	N3—N2	1.3071 (16)
C3—C3ii	1.378 (3)	N3—N4	1.3450 (17)
C3—H3	0.9300	N6—H6A	0.93 (2)
C4—N6	1.473 (2)	N6—H6B	0.88 (2)
N1i—Cu1—N1ii	180.0	H4B—C4—H4C	109.5
N1i—Cu1—N1	91.77 (6)	N6—C5—H5A	109.5
N1ii—Cu1—N1	88.23 (6)	N6—C5—H5B	109.5
N1i—Cu1—N1iii	88.23 (6)	H5A—C5—H5B	109.5
N1ii—Cu1—N1iii	91.77 (6)	N6—C5—H5C	109.5
N1—Cu1—N1iii	180.0	H5A—C5—H5C	109.5
N1i—Cu1—Cl1	88.82 (3)	H5B—C5—H5C	109.5
N1ii—Cu1—Cl1	91.18 (3)	C1—N1—N2	105.74 (10)
N1—Cu1—Cl1	91.18 (3)	C1—N1—N2	105.74 (10)
N1iii—Cu1—Cl1	88.82 (3)	C1—N1—Cu1	133.78 (9)
N4—C1—N1	110.40 (11)	N2—N1—Cu1	120.43 (8)
N4—C1—C2	121.69 (11)	N2—N1—Cu1	120.43 (8)
N1—C1—C2	127.80 (11)	N3—N2—N1	108.79 (10)
N5—C2—C2ii	121.15 (8)	N2—N3—N4	109.56 (11)
N5—C2—C1	114.09 (11)	N2—N3—N4	109.56 (11)
C2ii—C2—C1	124.68 (7)	C1—N4—N3	105.50 (10)
N5—C3—C3ii	121.98 (8)	C3—N5—C2	116.86 (13)
N5—C3—H3	119.0	C5—N6—C4	113.59 (13)
C3ii—C3—H3	119.0	C5—N6—H6A	108.9 (13)
N6—C4—H4A	109.5	C4—N6—H6A	110.8 (13)
N6—C4—H4B	109.5	C5—N6—H6B	111.8 (13)
H4A—C4—H4B	109.5	C4—N6—H6B	110.5 (13)
N6—C4—H4C	109.5	H6A—N6—H6B	100.5 (18)
H4A—C4—H4C	109.5
N4—C1—C2—N5	38.25 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6B···Cl1iii	0.88 (2)	2.32 (2)	3.1731 (13)	162.7 (18)
N6—H6A···N4iv	0.93 (2)	1.91 (2)	2.8381 (17)	175 (2)

Table 1

Selected bond lengths (Å)

Cu1—N1	2.0029 (10)
Cu1—Cl1	2.8719 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6B⋯Cl1i	0.88 (2)	2.32 (2)	3.1731 (13)	162.7 (18)
N6—H6A⋯N4ii	0.93 (2)	1.91 (2)	2.8381 (17)	175 (2)

Symmetry codes: (i) ; (ii) .