(Azido-κN)[6-meth-oxy-2-(2-pyridylmethyl-imino-meth-yl)phenolato-κN,N',O]copper(II).

The title compound, [Cu(C(14)H(13)N(2)O(2))(N(3))], is a monomeric neutral complex with one unsymmetrical 6-meth-oxy-2-(2-pyridylmethyl-imino-meth-yl)phenolate Schiff base ligand and one azide ligand. The mol-ecules are connected by a combination of two π-π inter-actions [centroid-centroid distances 3.359 (3) and 3.378 (2) Å] and one C-H⋯N hydrogen bond into a two-dimensional supra-molecular network structure.

Related literature

For related literature, see: Kannappan et al. (2005 ▶); Li & Zhang (2004 ▶); Ni & Wang (2007 ▶); Sun (2005 ▶); Yang (2005 ▶).

Experimental

Crystal data

[Cu(C14H13N2O2)(N3)]

M = 346.83

Triclinic,

a = 6.7197 (2) Å

b = 10.2820 (2) Å

c = 10.5549 (5) Å

α = 86.130 (2)°

β = 81.155 (2)°

γ = 76.289 (3)°

V = 699.69 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.58 mm−1

T = 293 (2) K

0.10 × 0.06 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.892, T max = 0.941

11804 measured reflections

3207 independent reflections

2815 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.090

S = 0.99

3207 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: XP (Sheldrick, 1998 ▶); software used to prepare material for publication: SHELXL97 and XP.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807046260/si2035sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807046260/si2035Isup2.hkl

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

[Cu(C14H13N2O2)(N3)]	Z = 2
Mr = 346.83	F000 = 354
Triclinic, P1	Dx = 1.646 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.7197 (2) Å	Cell parameters from 3207 reflections
b = 10.2820 (2) Å	θ = 2.0–27.5º
c = 10.5549 (5) Å	µ = 1.58 mm−1
α = 86.130 (2)º	T = 293 (2) K
β = 81.155 (2)º	Tiny block, brown
γ = 76.289 (3)º	0.10 × 0.06 × 0.04 mm
V = 699.69 (4) Å3

Bruker APEXII CCD area-detector diffractometer	3207 independent reflections
Radiation source: fine-focus sealed tube	2815 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 293(2) K	θmax = 27.5º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	h = −8→8
Tmin = 0.892, Tmax = 0.941	k = −13→13
11804 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.066P)2 + 0.0216P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
3207 reflections	Δρmax = 0.35 e Å−3
199 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.71363 (3)	0.01027 (2)	0.64642 (2)	0.03501 (10)
O1	0.6949 (2)	0.15473 (13)	0.52246 (13)	0.0419 (3)
O2	0.6515 (3)	0.38174 (15)	0.38914 (16)	0.0527 (4)
N1	0.6386 (4)	0.1355 (2)	0.78607 (19)	0.0566 (5)
N2	0.7302 (3)	0.21856 (17)	0.79457 (17)	0.0483 (4)
N3	0.8155 (4)	0.2994 (2)	0.8096 (3)	0.0735 (7)
N4	0.7379 (2)	−0.15134 (16)	0.76640 (16)	0.0373 (3)
N5	0.7842 (2)	−0.12500 (16)	0.51834 (16)	0.0357 (3)
C5	0.7893 (3)	−0.26937 (19)	0.7095 (2)	0.0380 (4)
C8	0.7789 (3)	0.0241 (2)	0.33149 (19)	0.0381 (4)
C12	0.7057 (3)	0.2671 (2)	0.3210 (2)	0.0411 (4)
C13	0.7266 (3)	0.14646 (19)	0.39683 (19)	0.0369 (4)
C1	0.7074 (3)	−0.1514 (2)	0.8959 (2)	0.0459 (5)
H1	0.6707	−0.0697	0.9363	0.055*
C2	0.7285 (4)	−0.2665 (3)	0.9697 (2)	0.0553 (6)
H2	0.7077	−0.2630	1.0587	0.066*
C3	0.7806 (4)	−0.3881 (2)	0.9112 (2)	0.0530 (6)
H3	0.7940	−0.4678	0.9599	0.064*
C4	0.8128 (3)	−0.3895 (2)	0.7786 (2)	0.0472 (5)
H4	0.8498	−0.4703	0.7366	0.057*
C7	0.8033 (3)	−0.1038 (2)	0.3957 (2)	0.0399 (4)
H7	0.8357	−0.1784	0.3448	0.048*
C9	0.8117 (3)	0.0253 (2)	0.1950 (2)	0.0467 (5)
H9	0.8470	−0.0553	0.1528	0.056*
C10	0.7921 (3)	0.1424 (2)	0.1258 (2)	0.0511 (5)
H10	0.8144	0.1418	0.0367	0.061*
C11	0.7386 (3)	0.2640 (2)	0.1881 (2)	0.0460 (5)
H11	0.7248	0.3439	0.1399	0.055*
C6	0.8206 (3)	−0.26431 (19)	0.5655 (2)	0.0426 (4)
H6A	0.9607	−0.3110	0.5335	0.051*
H6B	0.7257	−0.3085	0.5347	0.051*
C14	0.6187 (4)	0.5071 (2)	0.3204 (3)	0.0576 (6)
H14A	0.5820	0.5784	0.3799	0.086*
H14B	0.5087	0.5137	0.2703	0.086*
H14C	0.7431	0.5138	0.2646	0.086*

	U11	U22	U33	U12	U13	U23
Cu1	0.03917 (16)	0.03307 (14)	0.03272 (15)	−0.00818 (10)	−0.00430 (10)	−0.00288 (9)
O1	0.0541 (8)	0.0374 (7)	0.0338 (7)	−0.0092 (6)	−0.0065 (6)	−0.0025 (5)
O2	0.0669 (10)	0.0411 (8)	0.0486 (9)	−0.0096 (7)	−0.0097 (8)	0.0030 (7)
N1	0.0808 (14)	0.0462 (10)	0.0410 (11)	−0.0179 (10)	0.0068 (10)	−0.0107 (8)
N2	0.0719 (12)	0.0295 (8)	0.0380 (10)	0.0006 (8)	−0.0104 (8)	0.0000 (7)
N3	0.1041 (19)	0.0387 (11)	0.0809 (17)	−0.0149 (11)	−0.0245 (14)	−0.0045 (10)
N4	0.0354 (8)	0.0380 (8)	0.0394 (9)	−0.0103 (6)	−0.0063 (7)	0.0002 (7)
N5	0.0347 (8)	0.0356 (8)	0.0373 (9)	−0.0081 (6)	−0.0056 (7)	−0.0028 (6)
C5	0.0308 (9)	0.0383 (9)	0.0460 (11)	−0.0102 (7)	−0.0071 (8)	0.0020 (8)
C8	0.0348 (9)	0.0458 (10)	0.0343 (10)	−0.0103 (8)	−0.0047 (8)	−0.0024 (8)
C12	0.0353 (10)	0.0441 (11)	0.0444 (11)	−0.0095 (8)	−0.0083 (8)	0.0021 (8)
C13	0.0306 (9)	0.0443 (10)	0.0364 (11)	−0.0092 (7)	−0.0063 (7)	0.0007 (8)
C1	0.0487 (12)	0.0496 (12)	0.0393 (12)	−0.0124 (9)	−0.0057 (9)	0.0013 (9)
C2	0.0554 (13)	0.0672 (15)	0.0434 (13)	−0.0178 (11)	−0.0073 (10)	0.0111 (11)
C3	0.0510 (12)	0.0501 (12)	0.0586 (15)	−0.0169 (10)	−0.0101 (10)	0.0175 (10)
C4	0.0432 (11)	0.0391 (10)	0.0608 (14)	−0.0130 (8)	−0.0094 (10)	0.0055 (9)
C7	0.0393 (10)	0.0425 (10)	0.0387 (11)	−0.0090 (8)	−0.0040 (8)	−0.0108 (8)
C9	0.0495 (12)	0.0569 (12)	0.0345 (11)	−0.0123 (9)	−0.0060 (9)	−0.0072 (9)
C10	0.0501 (12)	0.0724 (15)	0.0308 (11)	−0.0144 (11)	−0.0072 (9)	0.0029 (10)
C11	0.0412 (11)	0.0548 (12)	0.0432 (12)	−0.0140 (9)	−0.0107 (9)	0.0108 (9)
C6	0.0483 (11)	0.0344 (9)	0.0454 (12)	−0.0087 (8)	−0.0068 (9)	−0.0056 (8)
C14	0.0596 (14)	0.0430 (12)	0.0701 (16)	−0.0115 (10)	−0.0144 (12)	0.0093 (11)

Cu1—O1	1.9062 (14)	C7—C8	1.423 (3)
Cu1—N1	1.9504 (19)	C7—H7	0.93
Cu1—N4	2.0106 (16)	C13—C8	1.419 (3)
Cu1—N5	1.9315 (16)	C13—C12	1.420 (3)
N1—N2	1.181 (3)	C5—C6	1.500 (3)
N2—N3	1.147 (3)	C1—C2	1.364 (3)
O1—C13	1.316 (2)	C1—H1	0.93
O2—C12	1.368 (3)	C3—C2	1.377 (4)
O2—C14	1.423 (3)	C3—H3	0.93
C11—C12	1.387 (3)	C9—C10	1.355 (3)
C11—C10	1.397 (3)	C9—C8	1.423 (3)
C11—H11	0.93	C9—H9	0.93
N5—C7	1.290 (3)	C6—H6A	0.97
N5—C6	1.461 (2)	C6—H6B	0.97
N4—C5	1.338 (3)	C14—H14A	0.96
N4—C1	1.351 (3)	C14—H14B	0.96
C4—C3	1.384 (3)	C14—H14C	0.96
C4—C5	1.380 (3)	C2—H2	0.93
C4—H4	0.93	C10—H10	0.93
O1—Cu1—N1	90.95 (7)	C4—C5—C6	121.54 (18)
O1—Cu1—N5	93.59 (6)	N4—C1—C2	122.5 (2)
N1—Cu1—N5	175.35 (7)	N4—C1—H1	118.8
O1—Cu1—N4	175.78 (5)	C2—C1—H1	118.8
N4—Cu1—N5	82.20 (7)	C4—C3—C2	118.7 (2)
N1—Cu1—N4	93.26 (8)	C4—C3—H3	120.6
N1—N2—N3	176.4 (2)	C2—C3—H3	120.6
C13—O1—Cu1	127.21 (13)	C10—C9—C8	120.8 (2)
C12—O2—C14	118.41 (18)	C10—C9—H9	119.6
C12—C11—C10	120.8 (2)	C8—C9—H9	119.6
C12—C11—H11	119.6	N2—N1—Cu1	122.36 (17)
C10—C11—H11	119.6	N5—C6—C5	109.75 (16)
C7—N5—C6	117.27 (17)	N5—C6—H6A	109.7
C7—N5—Cu1	126.15 (14)	C5—C6—H6A	109.7
C6—N5—Cu1	116.57 (13)	N5—C6—H6B	109.7
C5—N4—C1	118.20 (18)	C5—C6—H6B	109.7
C5—N4—Cu1	115.20 (14)	H6A—C6—H6B	108.2
C1—N4—Cu1	126.61 (14)	C9—C8—C13	120.07 (19)
C3—C4—C5	119.0 (2)	C9—C8—C7	116.64 (19)
C3—C4—H4	120.5	C13—C8—C7	123.29 (19)
C5—C4—H4	120.5	O2—C14—H14A	109.5
N5—C7—C8	125.60 (18)	O2—C14—H14B	109.5
N5—C7—H7	117.2	H14A—C14—H14B	109.5
C8—C7—H7	117.2	O2—C14—H14C	109.5
O1—C13—C8	124.15 (18)	H14A—C14—H14C	109.5
O1—C13—C12	118.36 (17)	H14B—C14—H14C	109.5
C8—C13—C12	117.49 (18)	C1—C2—C3	119.4 (2)
O2—C12—C11	124.42 (19)	C1—C2—H2	120.3
O2—C12—C13	114.87 (18)	C3—C2—H2	120.3
C11—C12—C13	120.70 (19)	C9—C10—C11	120.1 (2)
N4—C5—C4	122.2 (2)	C9—C10—H10	119.9
N4—C5—C6	116.27 (17)	C11—C10—H10	119.9

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N3i	0.93	2.49	3.189 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N3i	0.93	2.49	3.189 (2)	132

Symmetry code: (i) .