Bis{N-[5-(4-methoxy-phen-yl)-1,3,4-oxa-diazol-2-yl]ethanimidamidato}copper(II).

The title compound, [Cu(C(11)H(11)N(4)O(2))(2)], was prepared by solvothermal synthesis using 2-amino-5-(4-methoxy-phen-yl)-1,3,4-oxadiazole and copper sulfate penta-hydrate in an acetonitrile solution. The Cu(II) atom lies on an inversion center and is four-coordinated in a slightly distorted square-planar geometry by four N atoms of the ligands obtained from the formation of a bond between the amine N atom of the oxadiazole mol-ecule and the nitrile C atom of the solvent. In the crystal structure an inter-molecular N-H⋯N hydrogen bond links inversion-related mol-ecules.

Related literature

For comparative bond lengths in similar coordination compounds, see: Cai, (2009 ▶). For applications of complexes formed by Schiff base ligands, see: Lu & Schauss (2002 ▶). For chemotherapeutic effects of 2,5-substituted-1,3,4-oxadiazole derivatives, see: Cao et al. (2002 ▶); Kadi et al. (2007 ▶); Zareef et al. (2006 ▶, 2007 ▶, 2008 ▶).

Experimental

Crystal data

[Cu(C11H11N4O2)2]

M = 526.02

Triclinic,

a = 4.9020 (6) Å

b = 11.2083 (14) Å

c = 11.5739 (14) Å

α = 111.501 (5)°

β = 99.274 (6)°

γ = 91.564 (5)°

V = 581.33 (12) Å3

Z = 1

Mo Kα radiation

μ = 0.99 mm−1

T = 120 K

0.53 × 0.23 × 0.07 mm

Data collection

Bruker APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.707, T max = 0.933

6654 measured reflections

2633 independent reflections

2417 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.087

S = 1.06

2633 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009050/pk2228sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009050/pk2228Isup2.hkl

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

[Cu(C11H11N4O2)2]	Z = 1
Mr = 526.02	F(000) = 271
Triclinic, P1	Dx = 1.503 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9020 (6) Å	Cell parameters from 2925 reflections
b = 11.2083 (14) Å	θ = 3.2–27.4°
c = 11.5739 (14) Å	µ = 0.99 mm−1
α = 111.501 (5)°	T = 120 K
β = 99.274 (6)°	Plate, brown
γ = 91.564 (5)°	0.53 × 0.23 × 0.07 mm
V = 581.33 (12) Å3

Bruker APEXII diffractometer	2633 independent reflections
Radiation source: Enraf-Nonius FR590	2417 reflections with I > 2σ(I)
graphite	Rint = 0.035
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −6→6
Tmin = 0.707, Tmax = 0.933	k = −14→14
6654 measured reflections	l = −15→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0355P)2 + 0.2373P] where P = (Fo2 + 2Fc2)/3
2633 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0	0	0.5	0.02231 (12)
N1	0.1428 (3)	−0.09664 (16)	0.34848 (16)	0.0245 (4)
H1	0.0696	−0.1769	0.3098	0.029*
C2	0.3294 (4)	−0.06281 (19)	0.29405 (19)	0.0240 (4)
C3	0.3968 (5)	−0.1574 (2)	0.1722 (2)	0.0314 (5)
H3A	0.3138	−0.2438	0.1562	0.047*
H3B	0.5986	−0.1581	0.1794	0.047*
H3C	0.3216	−0.1314	0.1021	0.047*
N4	0.4749 (3)	0.05335 (16)	0.33696 (16)	0.0255 (4)
C5	0.4203 (4)	0.14395 (19)	0.44061 (19)	0.0229 (4)
N6	0.2379 (3)	0.14792 (15)	0.51450 (16)	0.0230 (4)
O7	0.5775 (3)	0.26005 (13)	0.48592 (13)	0.0244 (3)
N8	0.2771 (3)	0.26958 (16)	0.61315 (17)	0.0257 (4)
C9	0.4788 (4)	0.33114 (19)	0.59302 (19)	0.0234 (4)
C10	0.6076 (4)	0.46056 (19)	0.6693 (2)	0.0251 (4)
C11	0.5447 (5)	0.5265 (2)	0.7888 (2)	0.0368 (5)
H11	0.417	0.4865	0.8202	0.044*
C12	0.6665 (5)	0.6494 (2)	0.8615 (2)	0.0385 (6)
H12	0.6239	0.6931	0.9429	0.046*
C13	0.8519 (4)	0.70962 (19)	0.8158 (2)	0.0266 (4)
C14	0.9179 (5)	0.6449 (2)	0.6975 (2)	0.0309 (5)
H14	1.0455	0.6849	0.6661	0.037*
C15	0.7950 (5)	0.5211 (2)	0.6259 (2)	0.0321 (5)
H15	0.8404	0.4767	0.5452	0.038*
O16	0.9576 (3)	0.83100 (14)	0.89471 (14)	0.0336 (4)
C17	1.1494 (5)	0.8972 (2)	0.8518 (2)	0.0321 (5)
H17A	1.3138	0.8496	0.8384	0.048*
H17B	1.205	0.9841	0.9154	0.048*
H17C	1.0601	0.903	0.7722	0.048*

	U11	U22	U33	U12	U13	U23
Cu1	0.02216 (19)	0.01886 (19)	0.0244 (2)	−0.00107 (13)	0.00942 (14)	0.00450 (14)
N1	0.0251 (8)	0.0203 (8)	0.0251 (9)	−0.0016 (6)	0.0080 (7)	0.0039 (7)
C2	0.0251 (10)	0.0244 (10)	0.0225 (10)	0.0037 (8)	0.0058 (8)	0.0083 (8)
C3	0.0365 (12)	0.0275 (11)	0.0263 (11)	−0.0012 (9)	0.0110 (9)	0.0039 (9)
N4	0.0290 (9)	0.0231 (9)	0.0238 (9)	−0.0008 (7)	0.0106 (7)	0.0057 (7)
C5	0.0225 (9)	0.0206 (10)	0.0261 (10)	−0.0003 (7)	0.0048 (8)	0.0094 (8)
N6	0.0233 (8)	0.0199 (8)	0.0238 (8)	0.0002 (6)	0.0094 (7)	0.0040 (7)
O7	0.0277 (7)	0.0197 (7)	0.0247 (7)	−0.0024 (5)	0.0093 (6)	0.0056 (6)
N8	0.0266 (9)	0.0187 (8)	0.0279 (9)	−0.0001 (7)	0.0097 (7)	0.0027 (7)
C9	0.0247 (10)	0.0208 (10)	0.0243 (10)	0.0022 (8)	0.0081 (8)	0.0064 (8)
C10	0.0257 (10)	0.0203 (10)	0.0274 (11)	0.0015 (8)	0.0068 (8)	0.0060 (8)
C11	0.0446 (13)	0.0299 (12)	0.0344 (12)	−0.0070 (10)	0.0200 (11)	0.0061 (10)
C12	0.0540 (15)	0.0298 (12)	0.0281 (12)	−0.0058 (10)	0.0201 (11)	0.0021 (10)
C13	0.0294 (10)	0.0205 (10)	0.0265 (10)	−0.0013 (8)	0.0053 (9)	0.0053 (8)
C14	0.0354 (12)	0.0251 (11)	0.0305 (11)	−0.0060 (9)	0.0127 (9)	0.0061 (9)
C15	0.0397 (12)	0.0252 (11)	0.0257 (11)	−0.0046 (9)	0.0157 (9)	−0.0004 (9)
O16	0.0432 (9)	0.0231 (8)	0.0287 (8)	−0.0081 (6)	0.0108 (7)	0.0021 (6)
C17	0.0365 (12)	0.0225 (11)	0.0343 (12)	−0.0059 (9)	0.0070 (10)	0.0075 (9)

Cu1—N6i	1.9403 (16)	C9—C10	1.454 (3)
Cu1—N6	1.9403 (16)	C10—C15	1.386 (3)
Cu1—N1i	1.9451 (17)	C10—C11	1.398 (3)
Cu1—N1	1.9451 (17)	C11—C12	1.380 (3)
N1—C2	1.311 (3)	C11—H11	0.95
N1—H1	0.88	C12—C13	1.394 (3)
C2—N4	1.346 (3)	C12—H12	0.95
C2—C3	1.515 (3)	C13—O16	1.361 (2)
C3—H3A	0.98	C13—C14	1.390 (3)
C3—H3B	0.98	C14—C15	1.388 (3)
C3—H3C	0.98	C14—H14	0.95
N4—C5	1.329 (3)	C15—H15	0.95
C5—N6	1.324 (3)	O16—C17	1.436 (3)
C5—O7	1.370 (2)	C17—H17A	0.98
N6—N8	1.405 (2)	C17—H17B	0.98
O7—C9	1.377 (2)	C17—H17C	0.98
N8—C9	1.289 (2)
N6i—Cu1—N6	180.00 (6)	N8—C9—C10	127.92 (19)
N6i—Cu1—N1i	87.39 (7)	O7—C9—C10	119.18 (17)
N6—Cu1—N1i	92.61 (7)	C15—C10—C11	118.54 (19)
N6i—Cu1—N1	92.61 (7)	C15—C10—C9	121.09 (19)
N6—Cu1—N1	87.39 (7)	C11—C10—C9	120.36 (19)
N1i—Cu1—N1	180	C12—C11—C10	120.5 (2)
C2—N1—Cu1	131.13 (14)	C12—C11—H11	119.7
C2—N1—H1	114.4	C10—C11—H11	119.7
Cu1—N1—H1	114.4	C11—C12—C13	120.2 (2)
N1—C2—N4	125.48 (18)	C11—C12—H12	119.9
N1—C2—C3	120.38 (18)	C13—C12—H12	119.9
N4—C2—C3	114.13 (17)	O16—C13—C14	124.78 (19)
C2—C3—H3A	109.5	O16—C13—C12	115.32 (19)
C2—C3—H3B	109.5	C14—C13—C12	119.90 (19)
H3A—C3—H3B	109.5	C15—C14—C13	119.2 (2)
C2—C3—H3C	109.5	C15—C14—H14	120.4
H3A—C3—H3C	109.5	C13—C14—H14	120.4
H3B—C3—H3C	109.5	C10—C15—C14	121.6 (2)
C5—N4—C2	118.09 (17)	C10—C15—H15	119.2
N6—C5—N4	133.31 (18)	C14—C15—H15	119.2
N6—C5—O7	109.26 (17)	C13—O16—C17	117.41 (17)
N4—C5—O7	117.43 (17)	O16—C17—H17A	109.5
C5—N6—N8	108.50 (16)	O16—C17—H17B	109.5
C5—N6—Cu1	124.23 (14)	H17A—C17—H17B	109.5
N8—N6—Cu1	126.65 (13)	O16—C17—H17C	109.5
C5—O7—C9	104.03 (14)	H17A—C17—H17C	109.5
C9—N8—N6	105.28 (16)	H17B—C17—H17C	109.5
N8—C9—O7	112.90 (17)
N6i—Cu1—N1—C2	−177.96 (19)	N6—N8—C9—O7	0.9 (2)
N6—Cu1—N1—C2	2.04 (19)	N6—N8—C9—C10	−178.20 (19)
Cu1—N1—C2—N4	1.8 (3)	C5—O7—C9—N8	−1.4 (2)
Cu1—N1—C2—C3	−178.05 (14)	C5—O7—C9—C10	177.76 (17)
N1—C2—N4—C5	−2.6 (3)	N8—C9—C10—C15	−170.3 (2)
C3—C2—N4—C5	177.23 (17)	O7—C9—C10—C15	10.7 (3)
C2—N4—C5—N6	−2.5 (3)	N8—C9—C10—C11	9.8 (3)
C2—N4—C5—O7	177.53 (17)	O7—C9—C10—C11	−169.16 (19)
N4—C5—N6—N8	179.1 (2)	C15—C10—C11—C12	0.2 (4)
O7—C5—N6—N8	−0.9 (2)	C9—C10—C11—C12	180.0 (2)
N4—C5—N6—Cu1	7.6 (3)	C10—C11—C12—C13	0.7 (4)
O7—C5—N6—Cu1	−172.39 (12)	C11—C12—C13—O16	179.4 (2)
N1i—Cu1—N6—C5	174.14 (16)	C11—C12—C13—C14	−1.1 (4)
N1—Cu1—N6—C5	−5.86 (16)	O16—C13—C14—C15	−179.9 (2)
N1i—Cu1—N6—N8	4.22 (16)	C12—C13—C14—C15	0.6 (3)
N1—Cu1—N6—N8	−175.78 (16)	C11—C10—C15—C14	−0.6 (3)
N6—C5—O7—C9	1.4 (2)	C9—C10—C15—C14	179.6 (2)
N4—C5—O7—C9	−178.66 (17)	C13—C14—C15—C10	0.2 (4)
C5—N6—N8—C9	0.0 (2)	C14—C13—O16—C17	0.6 (3)
Cu1—N6—N8—C9	171.26 (14)	C12—C13—O16—C17	−179.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N8i	0.88	2.42	2.983 (2)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N8i	0.88	2.42	2.983 (2)	123

Symmetry code: (i) .