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The title compound, [Cu(C11H11N4O2)2], was prepared by solvothermal synthesis using 2-amino-5-(4-methoxy­phen­yl)-1,3,4-oxadiazole and copper sulfate penta­hydrate in an acetonitrile solution. The CuII 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 mol­ecule and the nitrile C atom of the solvent. In the crystal structure an inter­molecular N—H...N hydrogen bond links inversion-related mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810009050/pk2228sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810009050/pk2228Isup2.hkl
Contains datablock I

CCDC reference: 774138

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.087
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found




Alert level A PLAT900_ALERT_1_A No Matching Reflection File Found .............. ! PLAT900_ALERT_1_A No Matching Reflection File Found .............. ! PLAT902_ALERT_1_A No (Interpretable) Reflections found in FCF .... !
3 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In recent years, there has been a considerable effort towards preparation of new materials containing polyfunctional organic ligands able to bind metallic ions by solvothermal synthesis. For example, with Schiff bases ligands, such complexes could be applied in different areas, including biochemistry, electrochemistry, and catalysis (Lu et al., 2002).

The 2,5-substituted-1,3,4-oxadiazole derivatives are of significant interest due to their chemotherapeutic effects (Kadi et al., 2007; Zareef et al., 2008; Zareef et al., 2007; Zareef et al., 2006; Cao et al., 2002). In this paper, we report the structure of one of these compounds with copper (II).

In the centrosymmetric title complex, the Cu (II) atom is located on an inversion center and is four-coordinated in a square planar geometry by four N atoms of the ligands obtained from the formation of a bond between N-amine of the oxadiazole molecule and C-nitrile of the solvent. All the coordinated bond lengths are typical and comparable with those in similar copper (II) complexes (Cai,2009). In the title compound, there is just one weak hydrogen bond N1-H1···N8 linking different inversion (-x, -y, -Z+1) related molecules.

Related literature top

For comparative coordinated bond lengths, 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 top

5-(4-Methoxy-phenyl)-2amino-1, 3, 4-oxadiazole (0,2 mmole) and (0,1 mmole) copper sulfate pentahydrate were mixed in 5 ml of acetonitrile. The mixture was placed in a Teflon-lined stainless steel vessel, and heated to 160° C for 16 h. It was then cooled to room temperature over a period of 24 h, and washed using acetonitrile. Brown crystals suitable for X-Ray crystallography were obtained.

Refinement top

H atoms were placed at calculated positions (C-H = 0..88-0.98 Å) and were treated as riding on their parent atoms, with Uiso(H) set to 1.2-1.5 times Ueq(C).

Computing details top

Data collection: SAINT (Bruker, 2002); cell refinement: SMART (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound in 30% probability displacement ellipsoids for non-H atoms.
Bis{N-[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2- yl]ethanimidamidato}copper(II) top
Crystal data top
[Cu(C11H11N4O2)2]Z = 1
Mr = 526.02F(000) = 271
Triclinic, P1Dx = 1.503 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.9020 (6) ÅCell parameters from 2925 reflections
b = 11.2083 (14) Åθ = 3.2–27.4°
c = 11.5739 (14) ŵ = 0.99 mm1
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
Data collection top
Bruker APEXII
diffractometer
2633 independent reflections
Radiation source: Enraf-Nonius FR5902417 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
CCD rotation images, thin slices scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 66
Tmin = 0.707, Tmax = 0.933k = 1414
6654 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-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 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
[Cu(C11H11N4O2)2]γ = 91.564 (5)°
Mr = 526.02V = 581.33 (12) Å3
Triclinic, P1Z = 1
a = 4.9020 (6) ÅMo Kα radiation
b = 11.2083 (14) ŵ = 0.99 mm1
c = 11.5739 (14) ÅT = 120 K
α = 111.501 (5)°0.53 × 0.23 × 0.07 mm
β = 99.274 (6)°
Data collection top
Bruker APEXII
diffractometer
2633 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
2417 reflections with I > 2σ(I)
Tmin = 0.707, Tmax = 0.933Rint = 0.035
6654 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.087H-atom parameters constrained
S = 1.06Δρmax = 0.42 e Å3
2633 reflectionsΔρmin = 0.29 e Å3
166 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu1000.50.02231 (12)
N10.1428 (3)0.09664 (16)0.34848 (16)0.0245 (4)
H10.06960.17690.30980.029*
C20.3294 (4)0.06281 (19)0.29405 (19)0.0240 (4)
C30.3968 (5)0.1574 (2)0.1722 (2)0.0314 (5)
H3A0.31380.24380.15620.047*
H3B0.59860.15810.17940.047*
H3C0.32160.13140.10210.047*
N40.4749 (3)0.05335 (16)0.33696 (16)0.0255 (4)
C50.4203 (4)0.14395 (19)0.44061 (19)0.0229 (4)
N60.2379 (3)0.14792 (15)0.51450 (16)0.0230 (4)
O70.5775 (3)0.26005 (13)0.48592 (13)0.0244 (3)
N80.2771 (3)0.26958 (16)0.61315 (17)0.0257 (4)
C90.4788 (4)0.33114 (19)0.59302 (19)0.0234 (4)
C100.6076 (4)0.46056 (19)0.6693 (2)0.0251 (4)
C110.5447 (5)0.5265 (2)0.7888 (2)0.0368 (5)
H110.4170.48650.82020.044*
C120.6665 (5)0.6494 (2)0.8615 (2)0.0385 (6)
H120.62390.69310.94290.046*
C130.8519 (4)0.70962 (19)0.8158 (2)0.0266 (4)
C140.9179 (5)0.6449 (2)0.6975 (2)0.0309 (5)
H141.04550.68490.66610.037*
C150.7950 (5)0.5211 (2)0.6259 (2)0.0321 (5)
H150.84040.47670.54520.038*
O160.9576 (3)0.83100 (14)0.89471 (14)0.0336 (4)
C171.1494 (5)0.8972 (2)0.8518 (2)0.0321 (5)
H17A1.31380.84960.83840.048*
H17B1.2050.98410.91540.048*
H17C1.06010.9030.77220.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02216 (19)0.01886 (19)0.0244 (2)0.00107 (13)0.00942 (14)0.00450 (14)
N10.0251 (8)0.0203 (8)0.0251 (9)0.0016 (6)0.0080 (7)0.0039 (7)
C20.0251 (10)0.0244 (10)0.0225 (10)0.0037 (8)0.0058 (8)0.0083 (8)
C30.0365 (12)0.0275 (11)0.0263 (11)0.0012 (9)0.0110 (9)0.0039 (9)
N40.0290 (9)0.0231 (9)0.0238 (9)0.0008 (7)0.0106 (7)0.0057 (7)
C50.0225 (9)0.0206 (10)0.0261 (10)0.0003 (7)0.0048 (8)0.0094 (8)
N60.0233 (8)0.0199 (8)0.0238 (8)0.0002 (6)0.0094 (7)0.0040 (7)
O70.0277 (7)0.0197 (7)0.0247 (7)0.0024 (5)0.0093 (6)0.0056 (6)
N80.0266 (9)0.0187 (8)0.0279 (9)0.0001 (7)0.0097 (7)0.0027 (7)
C90.0247 (10)0.0208 (10)0.0243 (10)0.0022 (8)0.0081 (8)0.0064 (8)
C100.0257 (10)0.0203 (10)0.0274 (11)0.0015 (8)0.0068 (8)0.0060 (8)
C110.0446 (13)0.0299 (12)0.0344 (12)0.0070 (10)0.0200 (11)0.0061 (10)
C120.0540 (15)0.0298 (12)0.0281 (12)0.0058 (10)0.0201 (11)0.0021 (10)
C130.0294 (10)0.0205 (10)0.0265 (10)0.0013 (8)0.0053 (9)0.0053 (8)
C140.0354 (12)0.0251 (11)0.0305 (11)0.0060 (9)0.0127 (9)0.0061 (9)
C150.0397 (12)0.0252 (11)0.0257 (11)0.0046 (9)0.0157 (9)0.0004 (9)
O160.0432 (9)0.0231 (8)0.0287 (8)0.0081 (6)0.0108 (7)0.0021 (6)
C170.0365 (12)0.0225 (11)0.0343 (12)0.0059 (9)0.0070 (10)0.0075 (9)
Geometric parameters (Å, º) top
Cu1—N6i1.9403 (16)C9—C101.454 (3)
Cu1—N61.9403 (16)C10—C151.386 (3)
Cu1—N1i1.9451 (17)C10—C111.398 (3)
Cu1—N11.9451 (17)C11—C121.380 (3)
N1—C21.311 (3)C11—H110.95
N1—H10.88C12—C131.394 (3)
C2—N41.346 (3)C12—H120.95
C2—C31.515 (3)C13—O161.361 (2)
C3—H3A0.98C13—C141.390 (3)
C3—H3B0.98C14—C151.388 (3)
C3—H3C0.98C14—H140.95
N4—C51.329 (3)C15—H150.95
C5—N61.324 (3)O16—C171.436 (3)
C5—O71.370 (2)C17—H17A0.98
N6—N81.405 (2)C17—H17B0.98
O7—C91.377 (2)C17—H17C0.98
N8—C91.289 (2)
N6i—Cu1—N6180.00 (6)N8—C9—C10127.92 (19)
N6i—Cu1—N1i87.39 (7)O7—C9—C10119.18 (17)
N6—Cu1—N1i92.61 (7)C15—C10—C11118.54 (19)
N6i—Cu1—N192.61 (7)C15—C10—C9121.09 (19)
N6—Cu1—N187.39 (7)C11—C10—C9120.36 (19)
N1i—Cu1—N1180C12—C11—C10120.5 (2)
C2—N1—Cu1131.13 (14)C12—C11—H11119.7
C2—N1—H1114.4C10—C11—H11119.7
Cu1—N1—H1114.4C11—C12—C13120.2 (2)
N1—C2—N4125.48 (18)C11—C12—H12119.9
N1—C2—C3120.38 (18)C13—C12—H12119.9
N4—C2—C3114.13 (17)O16—C13—C14124.78 (19)
C2—C3—H3A109.5O16—C13—C12115.32 (19)
C2—C3—H3B109.5C14—C13—C12119.90 (19)
H3A—C3—H3B109.5C15—C14—C13119.2 (2)
C2—C3—H3C109.5C15—C14—H14120.4
H3A—C3—H3C109.5C13—C14—H14120.4
H3B—C3—H3C109.5C10—C15—C14121.6 (2)
C5—N4—C2118.09 (17)C10—C15—H15119.2
N6—C5—N4133.31 (18)C14—C15—H15119.2
N6—C5—O7109.26 (17)C13—O16—C17117.41 (17)
N4—C5—O7117.43 (17)O16—C17—H17A109.5
C5—N6—N8108.50 (16)O16—C17—H17B109.5
C5—N6—Cu1124.23 (14)H17A—C17—H17B109.5
N8—N6—Cu1126.65 (13)O16—C17—H17C109.5
C5—O7—C9104.03 (14)H17A—C17—H17C109.5
C9—N8—N6105.28 (16)H17B—C17—H17C109.5
N8—C9—O7112.90 (17)
N6i—Cu1—N1—C2177.96 (19)N6—N8—C9—O70.9 (2)
N6—Cu1—N1—C22.04 (19)N6—N8—C9—C10178.20 (19)
Cu1—N1—C2—N41.8 (3)C5—O7—C9—N81.4 (2)
Cu1—N1—C2—C3178.05 (14)C5—O7—C9—C10177.76 (17)
N1—C2—N4—C52.6 (3)N8—C9—C10—C15170.3 (2)
C3—C2—N4—C5177.23 (17)O7—C9—C10—C1510.7 (3)
C2—N4—C5—N62.5 (3)N8—C9—C10—C119.8 (3)
C2—N4—C5—O7177.53 (17)O7—C9—C10—C11169.16 (19)
N4—C5—N6—N8179.1 (2)C15—C10—C11—C120.2 (4)
O7—C5—N6—N80.9 (2)C9—C10—C11—C12180.0 (2)
N4—C5—N6—Cu17.6 (3)C10—C11—C12—C130.7 (4)
O7—C5—N6—Cu1172.39 (12)C11—C12—C13—O16179.4 (2)
N1i—Cu1—N6—C5174.14 (16)C11—C12—C13—C141.1 (4)
N1—Cu1—N6—C55.86 (16)O16—C13—C14—C15179.9 (2)
N1i—Cu1—N6—N84.22 (16)C12—C13—C14—C150.6 (3)
N1—Cu1—N6—N8175.78 (16)C11—C10—C15—C140.6 (3)
N6—C5—O7—C91.4 (2)C9—C10—C15—C14179.6 (2)
N4—C5—O7—C9178.66 (17)C13—C14—C15—C100.2 (4)
C5—N6—N8—C90.0 (2)C14—C13—O16—C170.6 (3)
Cu1—N6—N8—C9171.26 (14)C12—C13—O16—C17179.9 (2)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N8i0.882.422.983 (2)123
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formula[Cu(C11H11N4O2)2]
Mr526.02
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)4.9020 (6), 11.2083 (14), 11.5739 (14)
α, β, γ (°)111.501 (5), 99.274 (6), 91.564 (5)
V3)581.33 (12)
Z1
Radiation typeMo Kα
µ (mm1)0.99
Crystal size (mm)0.53 × 0.23 × 0.07
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.707, 0.933
No. of measured, independent and
observed [I > 2σ(I)] reflections
6654, 2633, 2417
Rint0.035
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.087, 1.06
No. of reflections2633
No. of parameters166
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.42, 0.29

Computer programs: SAINT (Bruker, 2002), SMART (Bruker, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N8i0.88002.42002.983 (2)123.00
Symmetry code: (i) x, y, z+1.
 

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