Di-μ(1,1)-azido-bis-[(2-{1-[2-(isopropyl-amino)ethyl-imino]eth-yl}phenolato)copper(II)].

In the centrosymmetric binuclear title complex, [Cu(2)(C(13)H(19)N(2)O)(2)(N(3))(2)], the Cu(II) atom adopts an elongated CuON(4) square-based pyramidal coordination geometry, arising from the N,N',O-tridentate ligand and two bridging end-on azide anions. The O atom is in the basal plane, one of the azide N atoms is in the apical site and the Cu⋯Cu separation is 3.2365 (3) Å. A pair of intra-molecular N-H⋯O hydrogen bonds helps to establish the mol-ecular conformation.

Related literature

For background to polynuclear complexes, see: Massoud et al. (2007 ▶); Lisnard et al. (2007 ▶); Sarkar et al. (2004 ▶); Escuer & Aromí (2006 ▶); Goher et al. (2001 ▶); Colacio et al. (2005 ▶); Sailaja et al. (2003 ▶); Cheng et al. (2006 ▶); Meyer et al. (2005 ▶); Sharma (1990 ▶); Ko et al. (2006 ▶); Escuer et al. (1998 ▶). For azido-bridged copper(II) complexes, see: Triki et al. (2005 ▶); Gao et al. (2005 ▶); Zhang et al. (2001 ▶).

Experimental

Crystal data

[Cu2(C13H19N2O)2(N3)2]

M = 649.74

Monoclinic,

a = 9.6558 (3) Å

b = 15.3021 (5) Å

c = 10.6549 (3) Å

β = 115.174 (1)°

V = 1424.78 (8) Å3

Z = 2

Mo Kα radiation

μ = 1.54 mm−1

T = 298 K

0.30 × 0.28 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.656, T max = 0.682

8486 measured reflections

3205 independent reflections

2700 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.068

S = 1.05

3205 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017174/hb5441sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017174/hb5441Isup2.hkl

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

[Cu2(C13H19N2O)2(N3)2]	F(000) = 676
Mr = 649.74	Dx = 1.515 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4033 reflections
a = 9.6558 (3) Å	θ = 2.5–28.4°
b = 15.3021 (5) Å	µ = 1.54 mm−1
c = 10.6549 (3) Å	T = 298 K
β = 115.174 (1)°	Block, blue
V = 1424.78 (8) Å3	0.30 × 0.28 × 0.27 mm
Z = 2

Bruker SMART CCD diffractometer	3205 independent reflections
Radiation source: fine-focus sealed tube	2700 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −12→12
Tmin = 0.656, Tmax = 0.682	k = −19→15
8486 measured reflections	l = −13→12

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) = 0.068	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0336P)2 + 0.2887P] where P = (Fo2 + 2Fc2)/3
3205 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.59044 (2)	0.085868 (13)	0.58341 (2)	0.02936 (8)
N1	0.79784 (16)	0.13417 (9)	0.67367 (16)	0.0338 (3)
N2	0.58778 (17)	0.13250 (10)	0.40334 (15)	0.0342 (3)
H2A	0.5430	0.0905	0.3380	0.041*
N3	0.36638 (17)	0.05814 (10)	0.48628 (16)	0.0365 (3)
N4	0.27481 (17)	0.08176 (10)	0.52619 (17)	0.0381 (4)
N5	0.1825 (3)	0.10262 (14)	0.5608 (3)	0.0738 (7)
O1	0.59002 (15)	0.04762 (10)	0.75079 (13)	0.0455 (3)
C1	0.7028 (2)	0.05405 (13)	0.87468 (19)	0.0389 (4)
C2	0.6797 (3)	0.01235 (15)	0.9831 (2)	0.0524 (5)
H2	0.5897	−0.0188	0.9615	0.063*
C3	0.7854 (3)	0.01630 (16)	1.1183 (2)	0.0628 (7)
H3	0.7662	−0.0110	1.1873	0.075*
C4	0.9211 (4)	0.06119 (17)	1.1520 (2)	0.0704 (8)
H4	0.9934	0.0643	1.2437	0.084*
C5	0.9482 (3)	0.10079 (15)	1.0498 (2)	0.0559 (6)
H5	1.0408	0.1297	1.0741	0.067*
C6	0.8418 (2)	0.09990 (12)	0.9086 (2)	0.0386 (4)
C7	0.8821 (2)	0.14202 (12)	0.8055 (2)	0.0373 (4)
C8	1.0266 (2)	0.19634 (16)	0.8554 (3)	0.0606 (6)
H8A	1.1115	0.1596	0.8663	0.091*
H8B	1.0449	0.2227	0.9429	0.091*
H8C	1.0150	0.2412	0.7887	0.091*
C9	0.8460 (2)	0.17343 (14)	0.5724 (2)	0.0443 (5)
H9A	0.9538	0.1620	0.5996	0.053*
H9B	0.8310	0.2362	0.5691	0.053*
C10	0.7519 (2)	0.13412 (13)	0.4315 (2)	0.0433 (5)
H10A	0.7652	0.1683	0.3608	0.052*
H10B	0.7868	0.0751	0.4283	0.052*
C11	0.5038 (2)	0.21591 (13)	0.3447 (2)	0.0434 (5)
H11	0.5600	0.2479	0.3014	0.052*
C12	0.4930 (3)	0.27349 (15)	0.4550 (3)	0.0587 (6)
H12A	0.4341	0.2444	0.4959	0.088*
H12B	0.4442	0.3275	0.4141	0.088*
H12C	0.5939	0.2852	0.5253	0.088*
C13	0.3461 (3)	0.19476 (17)	0.2336 (2)	0.0636 (6)
H13A	0.3555	0.1580	0.1646	0.095*
H13B	0.2948	0.2479	0.1911	0.095*
H13C	0.2880	0.1649	0.2745	0.095*

	U11	U22	U33	U12	U13	U23
Cu1	0.02708 (12)	0.03103 (13)	0.03107 (13)	−0.00587 (8)	0.01341 (9)	−0.00101 (9)
N1	0.0281 (7)	0.0312 (8)	0.0426 (9)	−0.0043 (6)	0.0154 (7)	−0.0021 (7)
N2	0.0403 (8)	0.0307 (8)	0.0337 (8)	−0.0058 (6)	0.0177 (7)	−0.0011 (6)
N3	0.0299 (8)	0.0390 (8)	0.0417 (9)	−0.0062 (6)	0.0163 (7)	−0.0048 (7)
N4	0.0319 (8)	0.0322 (8)	0.0478 (9)	−0.0015 (6)	0.0147 (7)	0.0014 (7)
N5	0.0586 (13)	0.0661 (14)	0.117 (2)	0.0054 (10)	0.0569 (14)	−0.0125 (13)
O1	0.0376 (7)	0.0671 (9)	0.0331 (7)	−0.0116 (7)	0.0163 (6)	0.0023 (7)
C1	0.0445 (10)	0.0405 (10)	0.0342 (10)	0.0072 (8)	0.0194 (8)	−0.0030 (8)
C2	0.0688 (14)	0.0548 (13)	0.0416 (12)	0.0089 (11)	0.0312 (11)	0.0021 (10)
C3	0.098 (2)	0.0558 (14)	0.0383 (12)	0.0221 (14)	0.0321 (13)	0.0041 (11)
C4	0.096 (2)	0.0579 (15)	0.0327 (12)	0.0248 (15)	0.0037 (12)	−0.0022 (11)
C5	0.0571 (13)	0.0470 (13)	0.0443 (12)	0.0090 (10)	0.0031 (10)	−0.0091 (10)
C6	0.0387 (10)	0.0325 (10)	0.0367 (10)	0.0073 (8)	0.0085 (8)	−0.0078 (8)
C7	0.0292 (9)	0.0293 (9)	0.0470 (11)	0.0014 (7)	0.0100 (8)	−0.0078 (8)
C8	0.0366 (11)	0.0606 (15)	0.0692 (15)	−0.0137 (10)	0.0077 (10)	−0.0124 (13)
C9	0.0340 (10)	0.0451 (11)	0.0589 (13)	−0.0066 (8)	0.0248 (9)	0.0039 (10)
C10	0.0486 (11)	0.0415 (11)	0.0541 (12)	−0.0014 (9)	0.0356 (10)	0.0051 (9)
C11	0.0492 (11)	0.0359 (10)	0.0447 (11)	−0.0013 (8)	0.0195 (9)	0.0110 (9)
C12	0.0685 (15)	0.0389 (12)	0.0668 (15)	0.0079 (11)	0.0272 (13)	−0.0025 (11)
C13	0.0588 (14)	0.0623 (16)	0.0517 (14)	0.0021 (12)	0.0062 (11)	0.0125 (12)

Cu1—O1	1.8786 (13)	C5—C6	1.416 (3)
Cu1—N1	1.9604 (14)	C5—H5	0.9300
Cu1—N3	2.0067 (15)	C6—C7	1.462 (3)
Cu1—N2	2.0369 (14)	C7—C8	1.513 (3)
Cu1—N3i	2.4175 (16)	C8—H8A	0.9600
N1—C7	1.295 (2)	C8—H8B	0.9600
N1—C9	1.473 (2)	C8—H8C	0.9600
N2—C10	1.482 (2)	C9—C10	1.510 (3)
N2—C11	1.499 (2)	C9—H9A	0.9700
N2—H2A	0.9100	C9—H9B	0.9700
N3—N4	1.189 (2)	C10—H10A	0.9700
N3—Cu1i	2.4175 (16)	C10—H10B	0.9700
N4—N5	1.145 (2)	C11—C12	1.507 (3)
O1—C1	1.310 (2)	C11—C13	1.514 (3)
C1—C2	1.417 (3)	C11—H11	0.9800
C1—C6	1.418 (3)	C12—H12A	0.9600
C2—C3	1.368 (3)	C12—H12B	0.9600
C2—H2	0.9300	C12—H12C	0.9600
C3—C4	1.384 (4)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.364 (4)	C13—H13C	0.9600
C4—H4	0.9300
O1—Cu1—N1	93.78 (6)	C1—C6—C7	123.53 (17)
O1—Cu1—N3	89.23 (6)	N1—C7—C6	121.92 (16)
N1—Cu1—N3	170.06 (6)	N1—C7—C8	119.49 (18)
O1—Cu1—N2	177.52 (6)	C6—C7—C8	118.59 (18)
N1—Cu1—N2	86.04 (6)	C7—C8—H8A	109.5
N3—Cu1—N2	90.54 (6)	C7—C8—H8B	109.5
O1—Cu1—N3i	94.47 (6)	H8A—C8—H8B	109.5
N1—Cu1—N3i	102.75 (5)	C7—C8—H8C	109.5
N3—Cu1—N3i	86.43 (6)	H8A—C8—H8C	109.5
N2—Cu1—N3i	87.98 (6)	H8B—C8—H8C	109.5
C7—N1—C9	120.54 (15)	N1—C9—C10	108.74 (15)
C7—N1—Cu1	127.34 (13)	N1—C9—H9A	109.9
C9—N1—Cu1	111.69 (12)	C10—C9—H9A	109.9
C10—N2—C11	114.37 (14)	N1—C9—H9B	109.9
C10—N2—Cu1	103.35 (11)	C10—C9—H9B	109.9
C11—N2—Cu1	118.59 (11)	H9A—C9—H9B	108.3
C10—N2—H2A	106.6	N2—C10—C9	110.37 (15)
C11—N2—H2A	106.6	N2—C10—H10A	109.6
Cu1—N2—H2A	106.6	C9—C10—H10A	109.6
N4—N3—Cu1	123.64 (13)	N2—C10—H10B	109.6
N4—N3—Cu1i	129.69 (12)	C9—C10—H10B	109.6
Cu1—N3—Cu1i	93.57 (6)	H10A—C10—H10B	108.1
N5—N4—N3	177.4 (2)	N2—C11—C12	112.19 (16)
C1—O1—Cu1	126.66 (12)	N2—C11—C13	109.26 (17)
O1—C1—C2	115.87 (18)	C12—C11—C13	110.81 (19)
O1—C1—C6	125.78 (17)	N2—C11—H11	108.2
C2—C1—C6	118.34 (19)	C12—C11—H11	108.2
C3—C2—C1	122.2 (2)	C13—C11—H11	108.2
C3—C2—H2	118.9	C11—C12—H12A	109.5
C1—C2—H2	118.9	C11—C12—H12B	109.5
C2—C3—C4	119.6 (2)	H12A—C12—H12B	109.5
C2—C3—H3	120.2	C11—C12—H12C	109.5
C4—C3—H3	120.2	H12A—C12—H12C	109.5
C5—C4—C3	119.7 (2)	H12B—C12—H12C	109.5
C5—C4—H4	120.2	C11—C13—H13A	109.5
C3—C4—H4	120.2	C11—C13—H13B	109.5
C4—C5—C6	123.0 (2)	H13A—C13—H13B	109.5
C4—C5—H5	118.5	C11—C13—H13C	109.5
C6—C5—H5	118.5	H13A—C13—H13C	109.5
C5—C6—C1	117.1 (2)	H13B—C13—H13C	109.5
C5—C6—C7	119.31 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.91	2.45	3.293 (2)	155

Table 1

Selected bond lengths (Å)

Cu1—O1	1.8786 (13)
Cu1—N1	1.9604 (14)
Cu1—N3	2.0067 (15)
Cu1—N2	2.0369 (14)
Cu1—N3i	2.4175 (16)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.91	2.45	3.293 (2)	155

Symmetry code: (i) .