Bis(N-nitroso-N-pentyl-hydroxy-laminato-κ(2) O,O')copper(II).

In the centrosymmetric title compound, [Cu(C5H11N2O2)2], the Cu(2+) ion, located on an inversion centre (Wyckoff position 2b), is in a square-planar environment, surounded by four O atoms of the N-O groups of two N-nitroso-N-pentyl-hydroxy-laminate ligands [Cu-O = 1.9042 (17) and 1.9095 (16) Å]. The hy-droxy-laminate monoanions are bidentate chelating ligands. The Cu(2+) cations form stacks along [010], with inter-molecular Cu⋯N contacts of 3.146 (2) and 3.653 (2) Å.

Related literature

The basic procedure for the synthesis of the reported complex is described by Zyuzin et al. (1997 ▶). For related structures of copper complexes with the N-nitroso­hydroxyl­amine derivatives, see: Abraham et al. (1987 ▶); Kovalchukova et al. (2013 ▶, 2014 ▶). The synthesis and properties of other metal nitroso­hydroxy­laminates are given in: Ahmed et al. (1988 ▶); Basson et al. (1992 ▶); Bolboaca et al. (2000 ▶); Kovalchukova et al. (2013 ▶); Najafi et al. (2011 ▶); Okabe & Tamaki (1995 ▶); Parkanyi et al. (1999 ▶); Pavel et al. (2000 ▶); Tamaki & Okabe (1998 ▶); Van der Helm et al. (1965 ▶). For applications of N-nitroso­hydroxyl­amine derivatives see: Lundell & Knowles (1920 ▶); Buscarons & Canela (1974 ▶); Oztekin & Erim (2000 ▶); McGill et al. (2000 ▶).

Experimental

Crystal data

[Cu(C5H11N2O2)2]

M = 325.86

Monoclinic,

a = 14.325 (3) Å

b = 4.776 (1) Å

c = 11.619 (2) Å

β = 103.82 (3)°

V = 771.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.43 mm−1

T = 293 K

0.80 × 0.20 × 0.03 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983 ▶) T min = 0.202, T max = 0.670

1509 measured reflections

1429 independent reflections

871 reflections with I > 2σ(I)

R int = 0.030

3 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.073

S = 0.88

1429 reflections

88 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.68 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1993 ▶); cell refinement: CAD-4-PC; data reduction: CAD-4-PC; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CIFTAB97 and SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814004978/pj2009sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004978/pj2009Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004978/pj2009Isup3.mol

CCDC reference: 989916

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Cu(C5H11N2O2)2]	F(000) = 342
Mr = 325.86	Dx = 1.402 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 14.325 (3) Å	θ = 9.7–11.9°
b = 4.776 (1) Å	µ = 1.43 mm−1
c = 11.619 (2) Å	T = 293 K
β = 103.82 (3)°	Plate, blue
V = 771.9 (3) Å3	0.80 × 0.20 × 0.03 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	871 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
β-filter monochromator	θmax = 25.5°, θmin = 2.9°
ω/2τ scans	h = −17→16
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983)	k = −5→0
Tmin = 0.202, Tmax = 0.670	l = 0→13
1509 measured reflections	3 standard reflections every 60 min
1429 independent reflections	intensity decay: none

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 0.88	w = 1/[σ2(Fo2) + (0.049P)2] where P = (Fo2 + 2Fc2)/3
1429 reflections	(Δ/σ)max < 0.001
88 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.68 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	0.5000	0.5000	0.04458 (15)
O1	0.38526 (12)	0.6395 (4)	0.39762 (14)	0.0498 (4)
O2	0.55742 (13)	0.7912 (3)	0.42774 (14)	0.0498 (4)
N1	0.40843 (14)	0.8595 (4)	0.34077 (15)	0.0447 (4)
N2	0.49421 (15)	0.9440 (4)	0.35334 (17)	0.0481 (5)
C1	0.33006 (17)	1.0104 (6)	0.26151 (19)	0.0506 (5)
H11	0.3559	1.1716	0.2288	0.061*
H12	0.2855	1.0778	0.3063	0.061*
C2	0.2767 (2)	0.8251 (6)	0.1611 (2)	0.0577 (6)
H21	0.3225	0.7366	0.1232	0.069*
H22	0.2431	0.6788	0.1928	0.069*
C3	0.20524 (19)	0.9925 (7)	0.0702 (2)	0.0647 (6)
H31	0.2394	1.1373	0.0383	0.078*
H32	0.1606	1.0840	0.1091	0.078*
C4	0.1491 (3)	0.8157 (8)	−0.0308 (3)	0.0848 (10)
H41	0.1094	0.6844	0.0000	0.102*
H42	0.1937	0.7083	−0.0641	0.102*
C5	0.0852 (3)	0.9888 (11)	−0.1285 (3)	0.1163 (15)
H51	0.0516	0.8669	−0.1903	0.174*
H52	0.1242	1.1171	−0.1603	0.174*
H53	0.0396	1.0918	−0.0966	0.174*

	U11	U22	U33	U12	U13	U23
Cu1	0.0460 (2)	0.0446 (2)	0.0432 (2)	−0.0028 (2)	0.01086 (14)	0.0008 (2)
O1	0.0449 (9)	0.0472 (9)	0.0562 (9)	−0.0053 (8)	0.0097 (7)	0.0084 (8)
O2	0.0473 (10)	0.0532 (9)	0.0505 (9)	−0.0062 (8)	0.0147 (7)	0.0020 (7)
N1	0.0485 (12)	0.0428 (11)	0.0428 (9)	−0.0033 (9)	0.0112 (8)	−0.0001 (8)
N2	0.0508 (12)	0.0499 (14)	0.0448 (10)	−0.0036 (9)	0.0137 (8)	0.0016 (8)
C1	0.0521 (13)	0.0470 (11)	0.0533 (11)	0.0052 (14)	0.0138 (10)	0.0037 (14)
C2	0.0538 (15)	0.0578 (16)	0.0584 (14)	0.0037 (13)	0.0073 (12)	−0.0015 (12)
C3	0.0556 (15)	0.0693 (15)	0.0641 (14)	0.0041 (17)	0.0042 (11)	0.0016 (17)
C4	0.069 (2)	0.092 (3)	0.081 (2)	0.0044 (19)	−0.0064 (16)	−0.0107 (19)
C5	0.099 (3)	0.140 (4)	0.086 (2)	−0.002 (3)	−0.025 (2)	−0.002 (3)

Cu1—O1	1.9042 (17)	C2—H21	0.9700
Cu1—O1i	1.9042 (17)	C2—H22	0.9700
Cu1—O2i	1.9095 (16)	C3—C4	1.512 (4)
Cu1—O2	1.9095 (16)	C3—H31	0.9700
O1—N1	1.325 (3)	C3—H32	0.9700
O2—N2	1.314 (2)	C4—C5	1.521 (5)
N1—N2	1.268 (3)	C4—H41	0.9700
N1—C1	1.461 (3)	C4—H42	0.9700
C1—C2	1.518 (4)	C5—H51	0.9600
C1—H11	0.9700	C5—H52	0.9600
C1—H12	0.9700	C5—H53	0.9600
C2—C3	1.512 (4)
O1—Cu1—O1i	180.0	C3—C2—H22	109.4
O1—Cu1—O2i	97.54 (7)	C1—C2—H22	109.4
O1i—Cu1—O2i	82.46 (7)	H21—C2—H22	108.0
O1—Cu1—O2	82.46 (7)	C2—C3—C4	113.1 (3)
O1i—Cu1—O2	97.54 (7)	C2—C3—H31	109.0
O2i—Cu1—O2	180.0	C4—C3—H31	109.0
N1—O1—Cu1	107.90 (13)	C2—C3—H32	109.0
N2—O2—Cu1	113.09 (14)	C4—C3—H32	109.0
N2—N1—O1	123.09 (19)	H31—C3—H32	107.8
N2—N1—C1	119.6 (2)	C3—C4—C5	112.9 (3)
O1—N1—C1	117.35 (19)	C3—C4—H41	109.0
N1—N2—O2	113.32 (18)	C5—C4—H41	109.0
N1—C1—C2	111.5 (2)	C3—C4—H42	109.0
N1—C1—H11	109.3	C5—C4—H42	109.0
C2—C1—H11	109.3	H41—C4—H42	107.8
N1—C1—H12	109.3	C4—C5—H51	109.5
C2—C1—H12	109.3	C4—C5—H52	109.5
H11—C1—H12	108.0	H51—C5—H52	109.5
C3—C2—C1	111.2 (2)	C4—C5—H53	109.5
C3—C2—H21	109.4	H51—C5—H53	109.5
C1—C2—H21	109.4	H52—C5—H53	109.5