Di-μ-azido-bis-({N'-[1-(2-pyrid-yl-κN)ethyl-idene]acetohydrazidato-κN',O}dicopper(II)).

The dimeric title compound, [Cu(2)(C(9)H(10)N(3)O)(2)(N(3))(2)], is located on a crystallographic inversion center. The Cu atom is coordinated by a tridentate anionic hydrazone ligand and two bridging azide ligands in a distorted square-pyramidal coordination geometry. The non-bonding Cu⋯Cu distance is 3.238 (1) Å. Non-classical inter-molecular C-H⋯N hydrogen bonds link the dimers into chains along the c axis.

Related literature

For related dimeric copper(II) complexes with similar tridentate ligands, see: Recio Despaigne et al. (2009 ▶); Sen et al. (2007 ▶); Patole et al. (2003 ▶).

Experimental

Crystal data

[Cu2(C9H10N3O)2(N3)2]

M = 563.54

Triclinic,

a = 7.589 (3) Å

b = 8.955 (3) Å

c = 9.693 (4) Å

α = 66.534 (15)°

β = 69.461 (13)°

γ = 81.468 (16)°

V = 565.8 (4) Å3

Z = 1

Mo Kα radiation

μ = 1.92 mm−1

T = 150 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.645, T max = 0.700

3858 measured reflections

2358 independent reflections

1591 reflections with I > 2σ

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.093

S = 1.08

2358 reflections

156 parameters

H-atom parameters constrained

Δρmax = 2.08 e Å−3

Δρmin = −2.81 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: DIAMOND (Brandenburg, 2006 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034860/pv2324sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034860/pv2324Isup2.hkl

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

[Cu2(C9H10N3O)2(N3)2]	Z = 1
Mr = 563.54	F(000) = 286
Triclinic, P1	Dx = 1.654 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.589 (3) Å	Cell parameters from 3185 reflections
b = 8.955 (3) Å	θ = 2.9–28.5°
c = 9.693 (4) Å	µ = 1.92 mm−1
α = 66.534 (15)°	T = 150 K
β = 69.461 (13)°	Prism, brown
γ = 81.468 (16)°	0.25 × 0.20 × 0.20 mm
V = 565.8 (4) Å3

Bruker SMART APEXII diffractometer	2358 independent reflections
Radiation source: fine-focus sealed tube	1591 reflections with I > 2σ
graphite	Rint = 0.040
ω scans	θmax = 27.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
Tmin = 0.645, Tmax = 0.700	k = −11→10
3858 measured reflections	l = −12→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)] = 0.027	Hydrogen site location: difference Fourier map
wR(F2) = 0.093	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0597P)2] where P = (Fo2 + 2Fc2)/3
2358 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 2.08 e Å−3
0 restraints	Δρmin = −2.81 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	0.34274 (3)	0.93665 (3)	0.95880 (3)	0.02989 (14)
N5	0.2011 (2)	0.7390 (2)	1.0402 (2)	0.0307 (5)
O1	0.4938 (2)	0.8357 (2)	0.8052 (2)	0.0380 (5)
N1	0.4648 (3)	1.1498 (2)	0.8642 (2)	0.0329 (5)
N6	0.2719 (3)	0.6294 (3)	0.9663 (2)	0.0367 (6)
C8	0.4270 (3)	0.6937 (3)	0.8443 (3)	0.0314 (6)
N2	0.5605 (3)	1.2073 (2)	0.7250 (2)	0.0358 (6)
N4	0.1206 (2)	0.9791 (2)	1.1350 (2)	0.0315 (5)
C1	−0.0012 (3)	0.8504 (3)	1.2187 (3)	0.0341 (6)
C2	−0.1553 (3)	0.8504 (4)	1.3488 (3)	0.0438 (8)
H2	−0.2404	0.7619	1.4036	0.053*
C9	0.5264 (3)	0.5944 (3)	0.7465 (3)	0.0436 (7)
H9A	0.4938	0.6357	0.6483	0.065*
H9B	0.4881	0.4806	0.8067	0.065*
H9C	0.6627	0.6019	0.7202	0.065*
C5	0.0911 (3)	1.1048 (3)	1.1831 (3)	0.0390 (7)
H5	0.1758	1.1935	1.1254	0.047*
C6	0.0467 (3)	0.7153 (3)	1.1593 (3)	0.0351 (7)
C3	−0.1850 (3)	0.9815 (4)	1.3992 (3)	0.0470 (9)
H3	−0.2888	0.9825	1.4891	0.056*
C4	−0.0596 (4)	1.1095 (4)	1.3148 (3)	0.0449 (7)
H4	−0.0761	1.1997	1.3465	0.054*
N3	0.6520 (4)	1.2683 (4)	0.5959 (3)	0.0644 (10)
C7	−0.0748 (4)	0.5681 (4)	1.2321 (4)	0.0564 (10)
H7A	−0.0411	0.5099	1.1594	0.085*
H7B	−0.2073	0.6022	1.2516	0.085*
H7C	−0.0556	0.4962	1.3328	0.085*

	U11	U22	U33	U12	U13	U23
Cu1	0.03078 (16)	0.0297 (2)	0.02843 (18)	−0.00779 (10)	−0.00486 (12)	−0.01154 (14)
N5	0.0319 (7)	0.0317 (10)	0.0289 (9)	−0.0042 (7)	−0.0062 (7)	−0.0133 (8)
O1	0.0400 (8)	0.0382 (10)	0.0350 (9)	−0.0100 (6)	−0.0044 (7)	−0.0163 (8)
N1	0.0386 (8)	0.0306 (10)	0.0287 (9)	−0.0063 (7)	−0.0068 (8)	−0.0117 (9)
N6	0.0383 (9)	0.0368 (11)	0.0351 (10)	−0.0048 (8)	−0.0079 (9)	−0.0154 (9)
C8	0.0389 (9)	0.0296 (11)	0.0318 (10)	−0.0017 (8)	−0.0140 (9)	−0.0148 (9)
N2	0.0404 (9)	0.0327 (10)	0.0316 (10)	−0.0034 (7)	−0.0105 (8)	−0.0091 (9)
N4	0.0303 (7)	0.0331 (10)	0.0310 (9)	−0.0027 (6)	−0.0079 (7)	−0.0126 (8)
C1	0.0286 (8)	0.0403 (12)	0.0295 (11)	−0.0040 (7)	−0.0073 (8)	−0.0098 (10)
C2	0.0346 (10)	0.0535 (16)	0.0353 (12)	−0.0070 (9)	−0.0012 (9)	−0.0150 (13)
C9	0.0495 (12)	0.0421 (15)	0.0402 (13)	−0.0022 (10)	−0.0097 (11)	−0.0200 (12)
C5	0.0395 (10)	0.0399 (14)	0.0386 (12)	−0.0032 (9)	−0.0109 (10)	−0.0162 (12)
C6	0.0323 (9)	0.0352 (12)	0.0343 (11)	−0.0074 (8)	−0.0070 (9)	−0.0102 (10)
C3	0.0388 (10)	0.0623 (19)	0.0358 (13)	0.0030 (10)	−0.0028 (10)	−0.0234 (14)
C4	0.0484 (12)	0.0489 (16)	0.0437 (14)	0.0071 (10)	−0.0130 (11)	−0.0277 (12)
N3	0.0746 (16)	0.0654 (19)	0.0323 (12)	−0.0125 (13)	−0.0042 (12)	−0.0045 (14)
C7	0.0493 (13)	0.0495 (18)	0.0599 (19)	−0.0198 (12)	0.0053 (13)	−0.0229 (16)

Cu1—N5	1.941 (2)	C1—C6	1.484 (4)
Cu1—N1	1.969 (2)	C2—C3	1.403 (5)
Cu1—O1	1.979 (2)	C2—H2	0.9500
Cu1—N4	2.051 (2)	C9—H9A	0.9800
Cu1—N1i	2.4574 (18)	C9—H9B	0.9800
N5—C6	1.297 (3)	C9—H9C	0.9800
N5—N6	1.377 (4)	C5—C4	1.394 (4)
O1—C8	1.300 (3)	C5—H5	0.9500
N1—N2	1.218 (3)	C6—C7	1.500 (3)
N1—Cu1i	2.4574 (18)	C3—C4	1.386 (4)
N6—C8	1.341 (3)	C3—H3	0.9500
C8—C9	1.493 (5)	C4—H4	0.9500
N2—N3	1.142 (3)	C7—H7A	0.9800
N4—C5	1.343 (4)	C7—H7B	0.9800
N4—C1	1.374 (3)	C7—H7C	0.9800
C1—C2	1.387 (4)
N5—Cu1—N1	173.44 (6)	C1—C2—C3	119.8 (2)
N5—Cu1—O1	79.78 (9)	C1—C2—H2	120.1
N1—Cu1—O1	101.14 (9)	C3—C2—H2	120.1
N5—Cu1—N4	80.27 (9)	C8—C9—H9A	109.5
N1—Cu1—N4	98.12 (10)	C8—C9—H9B	109.5
O1—Cu1—N4	159.42 (8)	H9A—C9—H9B	109.5
N5—Cu1—N1i	99.67 (7)	C8—C9—H9C	109.5
N1—Cu1—N1i	86.64 (6)	H9A—C9—H9C	109.5
O1—Cu1—N1i	98.75 (8)	H9B—C9—H9C	109.5
N4—Cu1—N1i	89.51 (8)	N4—C5—C4	122.3 (2)
C6—N5—N6	123.0 (2)	N4—C5—H5	118.9
C6—N5—Cu1	119.7 (2)	C4—C5—H5	118.9
N6—N5—Cu1	117.28 (14)	N5—C6—C1	113.21 (19)
C8—O1—Cu1	110.27 (16)	N5—C6—C7	124.6 (3)
N2—N1—Cu1	122.4 (2)	C1—C6—C7	122.2 (3)
N2—N1—Cu1i	111.79 (13)	C4—C3—C2	118.5 (3)
Cu1—N1—Cu1i	93.36 (6)	C4—C3—H3	120.7
C8—N6—N5	107.9 (2)	C2—C3—H3	120.7
O1—C8—N6	124.6 (3)	C3—C4—C5	119.4 (3)
O1—C8—C9	118.6 (2)	C3—C4—H4	120.3
N6—C8—C9	116.8 (2)	C5—C4—H4	120.3
N3—N2—N1	176.3 (3)	C6—C7—H7A	109.5
C5—N4—C1	119.0 (2)	C6—C7—H7B	109.5
C5—N4—Cu1	128.98 (15)	H7A—C7—H7B	109.5
C1—N4—Cu1	111.8 (2)	C6—C7—H7C	109.5
N4—C1—C2	121.1 (3)	H7A—C7—H7C	109.5
N4—C1—C6	114.9 (2)	H7B—C7—H7C	109.5
C2—C1—C6	124.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···N3ii	0.98	2.74	3.710 (4)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯N3i	0.98	2.74	3.710 (4)	171

Symmetry code: (i) .