(Azido-κN){(E)-2-[1-(pyridin-2-yl)ethyl-idene-amino]-phenolato-κ(3) N,N',O}copper(II).

In the title complex, [Cu(C13H11N2O)(N3)], the Cu(II) cation is four-coordinated by an N2O donor set of the tridentate Schiff base ligand and by the terminal N atom of the azide anion, forming a slightly distorted square-planar configuration.

Related literature

For related structures, see: Talukder et al. (2004 ▶); Sun (2008 ▶); Wang et al. (2012 ▶); Yu (2012 ▶). For the synthesis, see: Shita et al. (2009 ▶).

Experimental

Crystal data

[Cu(C13H11N2O)(N3)]

M = 316.81

Monoclinic,

a = 6.5881 (3) Å

b = 10.1576 (3) Å

c = 18.3884 (7) Å

β = 92.810 (3)°

V = 1229.06 (8) Å3

Z = 4

Cu Kα radiation

μ = 2.54 mm−1

T = 120 K

0.57 × 0.31 × 0.04 mm

Data collection

Agilent Xcalibur Gemini ultra diffractometer with Eos detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) ▶ T min = 0.709, T max = 1.000

4723 measured reflections

2357 independent reflections

2180 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.092

S = 1.05

2357 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and WinGX32 (Farrugia, 2012 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813019570/lr2111sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019570/lr2111Isup2.hkl

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

[Cu(C13H11CuN2O)(N3)]	F(000) = 644
Mr = 316.81	Dx = 1.712 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 2697 reflections
a = 6.5881 (3) Å	θ = 4.4–71.9°
b = 10.1576 (3) Å	µ = 2.54 mm−1
c = 18.3884 (7) Å	T = 120 K
β = 92.810 (3)°	Plate, green
V = 1229.06 (8) Å3	0.57 × 0.31 × 0.04 mm
Z = 4

Agilent Xcalibur Gemini ultra diffractometer with Eos detector	2357 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2180 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.021
Detector resolution: 16.1183 pixels mm-1	θmax = 72.0°, θmin = 4.8°
ω scans	h = −8→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→12
Tmin = 0.709, Tmax = 1.000	l = −21→22
4723 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.5226P] where P = (Fo2 + 2Fc2)/3
2357 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C11	0.1572 (3)	0.7721 (2)	0.10880 (11)	0.0224 (4)
H11	0.1311	0.8364	0.1447	0.027*
C12	0.1511 (3)	0.80806 (19)	0.03531 (13)	0.0238 (4)
H12	0.1217	0.8965	0.0216	0.029*
C13	0.1878 (3)	0.7152 (2)	−0.01764 (11)	0.0214 (4)
H13	0.1842	0.7401	−0.0675	0.026*
N3	0.3338 (3)	0.14937 (18)	0.06852 (10)	0.0267 (4)
N4	0.1971 (3)	0.12200 (16)	0.10667 (9)	0.0225 (4)
N5	0.0684 (3)	0.09080 (19)	0.14363 (10)	0.0300 (4)
C1	0.3018 (3)	0.3279 (2)	−0.13806 (11)	0.0190 (4)
C2	0.3721 (3)	0.1131 (2)	−0.10036 (11)	0.0233 (4)
H2	0.3975	0.0518	−0.0620	0.028*
C3	0.3734 (3)	0.0698 (2)	−0.17231 (12)	0.0270 (4)
H3	0.3992	−0.0201	−0.1829	0.032*
C4	0.3368 (3)	0.1587 (2)	−0.22775 (12)	0.0281 (5)
H4	0.3346	0.1309	−0.2771	0.034*
C5	0.3030 (3)	0.2905 (2)	−0.21045 (11)	0.0250 (4)
H5	0.2809	0.3539	−0.2480	0.030*
C6	0.2590 (3)	0.4639 (2)	−0.11276 (10)	0.0190 (4)
C7	0.2071 (3)	0.5713 (2)	−0.16602 (11)	0.0269 (4)
H7A	0.0753	0.6095	−0.1553	0.040*
H7B	0.2001	0.5351	−0.2155	0.040*
H7C	0.3120	0.6397	−0.1622	0.040*
C8	0.2306 (3)	0.58395 (19)	0.00240 (10)	0.0176 (4)
C9	0.2387 (3)	0.54692 (19)	0.07755 (10)	0.0181 (4)
C10	0.2008 (3)	0.6441 (2)	0.12986 (11)	0.0208 (4)
H10	0.2053	0.6214	0.1800	0.025*
N1	0.3362 (2)	0.23872 (17)	−0.08411 (9)	0.0193 (3)
N2	0.2667 (2)	0.47613 (16)	−0.04273 (9)	0.0172 (3)
O1	0.2789 (2)	0.42425 (13)	0.09719 (7)	0.0201 (3)
Cu1	0.31041 (4)	0.31370 (3)	0.014256 (14)	0.01721 (13)

	U11	U22	U33	U12	U13	U23
C11	0.0158 (9)	0.0196 (10)	0.0318 (11)	−0.0014 (7)	0.0007 (8)	−0.0067 (8)
C12	0.0179 (10)	0.0169 (10)	0.0362 (12)	−0.0003 (7)	−0.0015 (8)	−0.0001 (8)
C13	0.0173 (10)	0.0203 (10)	0.0262 (10)	−0.0010 (7)	−0.0023 (8)	0.0030 (8)
N3	0.0297 (10)	0.0213 (8)	0.0294 (9)	0.0053 (7)	0.0047 (8)	0.0048 (7)
N4	0.0305 (9)	0.0141 (8)	0.0221 (8)	0.0025 (7)	−0.0051 (7)	−0.0003 (6)
N5	0.0361 (10)	0.0259 (9)	0.0278 (9)	−0.0051 (8)	0.0021 (8)	0.0035 (8)
C1	0.0107 (9)	0.0248 (10)	0.0213 (9)	0.0000 (7)	0.0001 (7)	0.0001 (8)
C2	0.0186 (9)	0.0242 (10)	0.0271 (10)	0.0020 (8)	0.0013 (7)	−0.0035 (8)
C3	0.0209 (10)	0.0283 (11)	0.0320 (11)	−0.0001 (8)	0.0019 (8)	−0.0091 (9)
C4	0.0211 (10)	0.0381 (12)	0.0253 (10)	−0.0010 (9)	0.0020 (8)	−0.0096 (9)
C5	0.0190 (10)	0.0330 (11)	0.0230 (10)	0.0007 (8)	0.0010 (8)	−0.0004 (9)
C6	0.0117 (8)	0.0239 (10)	0.0215 (9)	0.0010 (7)	0.0015 (7)	0.0035 (8)
C7	0.0322 (11)	0.0283 (11)	0.0202 (9)	0.0067 (9)	0.0017 (8)	0.0039 (8)
C8	0.0117 (8)	0.0191 (9)	0.0220 (9)	−0.0007 (7)	0.0006 (7)	−0.0001 (7)
C9	0.0124 (8)	0.0184 (9)	0.0236 (9)	−0.0006 (7)	0.0017 (7)	−0.0008 (8)
C10	0.0157 (9)	0.0233 (10)	0.0233 (9)	−0.0006 (7)	0.0012 (7)	−0.0021 (8)
N1	0.0139 (7)	0.0221 (8)	0.0218 (8)	0.0013 (6)	0.0016 (6)	−0.0016 (7)
N2	0.0123 (7)	0.0193 (8)	0.0199 (7)	−0.0003 (6)	0.0000 (6)	0.0018 (6)
O1	0.0241 (7)	0.0180 (7)	0.0182 (6)	0.0025 (5)	0.0011 (5)	0.0012 (5)
Cu1	0.0182 (2)	0.01587 (19)	0.01753 (19)	0.00191 (10)	0.00069 (12)	0.00060 (10)

C11—C10	1.383 (3)	C3—H3	0.9500
C11—C12	1.399 (3)	C4—C5	1.396 (3)
C11—H11	0.9500	C4—H4	0.9500
C12—C13	1.385 (3)	C5—H5	0.9500
C12—H12	0.9500	C6—N2	1.292 (3)
C13—C8	1.408 (3)	C6—C7	1.495 (3)
C13—H13	0.9500	C7—H7A	0.9800
N3—N4	1.201 (3)	C7—H7B	0.9800
N3—Cu1	1.9470 (18)	C7—H7C	0.9800
N4—N5	1.157 (3)	C8—N2	1.402 (3)
C1—N1	1.354 (3)	C8—C9	1.431 (3)
C1—C5	1.385 (3)	C9—O1	1.320 (2)
C1—C6	1.489 (3)	C9—C10	1.409 (3)
C2—N1	1.334 (3)	C10—H10	0.9500
C2—C3	1.395 (3)	N1—Cu1	1.9775 (16)
C2—H2	0.9500	N2—Cu1	1.9682 (16)
C3—C4	1.375 (3)	O1—Cu1	1.9134 (14)
C10—C11—C12	120.79 (18)	C6—C7—H7A	109.5
C10—C11—H11	119.6	C6—C7—H7B	109.5
C12—C11—H11	119.6	H7A—C7—H7B	109.5
C13—C12—C11	120.23 (19)	C6—C7—H7C	109.5
C13—C12—H12	119.9	H7A—C7—H7C	109.5
C11—C12—H12	119.9	H7B—C7—H7C	109.5
C12—C13—C8	120.02 (19)	N2—C8—C13	128.50 (18)
C12—C13—H13	120.0	N2—C8—C9	111.54 (17)
C8—C13—H13	120.0	C13—C8—C9	119.96 (18)
N4—N3—Cu1	117.06 (14)	O1—C9—C10	120.94 (18)
N5—N4—N3	177.4 (2)	O1—C9—C8	120.65 (17)
N1—C1—C5	120.84 (19)	C10—C9—C8	118.41 (18)
N1—C1—C6	114.76 (17)	C11—C10—C9	120.59 (19)
C5—C1—C6	124.37 (19)	C11—C10—H10	119.7
N1—C2—C3	121.6 (2)	C9—C10—H10	119.7
N1—C2—H2	119.2	C2—N1—C1	120.03 (17)
C3—C2—H2	119.2	C2—N1—Cu1	126.68 (14)
C4—C3—C2	119.1 (2)	C1—N1—Cu1	113.19 (14)
C4—C3—H3	120.4	C6—N2—C8	131.76 (18)
C2—C3—H3	120.4	C6—N2—Cu1	116.57 (14)
C3—C4—C5	119.0 (2)	C8—N2—Cu1	111.37 (12)
C3—C4—H4	120.5	C9—O1—Cu1	111.35 (12)
C5—C4—H4	120.5	O1—Cu1—N3	95.95 (7)
C1—C5—C4	119.3 (2)	O1—Cu1—N2	85.04 (6)
C1—C5—H5	120.3	N3—Cu1—N2	175.89 (7)
C4—C5—H5	120.3	O1—Cu1—N1	166.56 (7)
N2—C6—C1	113.71 (17)	N3—Cu1—N1	97.49 (8)
N2—C6—C7	125.38 (19)	N2—Cu1—N1	81.53 (7)
C1—C6—C7	120.89 (17)
C10—C11—C12—C13	0.3 (3)	C7—C6—N2—C8	0.6 (3)
C11—C12—C13—C8	0.3 (3)	C1—C6—N2—Cu1	−4.7 (2)
Cu1—N3—N4—N5	166 (5)	C7—C6—N2—Cu1	173.67 (15)
N1—C2—C3—C4	0.0 (3)	C13—C8—N2—C6	−4.9 (3)
C2—C3—C4—C5	1.1 (3)	C9—C8—N2—C6	174.29 (18)
N1—C1—C5—C4	1.1 (3)	C13—C8—N2—Cu1	−178.26 (16)
C6—C1—C5—C4	−177.32 (19)	C9—C8—N2—Cu1	0.96 (18)
C3—C4—C5—C1	−1.6 (3)	C10—C9—O1—Cu1	177.20 (14)
N1—C1—C6—N2	1.7 (2)	C8—C9—O1—Cu1	−2.2 (2)
C5—C1—C6—N2	−179.81 (18)	C9—O1—Cu1—N3	−173.93 (13)
N1—C1—C6—C7	−176.72 (17)	C9—O1—Cu1—N2	2.06 (12)
C5—C1—C6—C7	1.7 (3)	C9—O1—Cu1—N1	5.2 (3)
C12—C13—C8—N2	178.35 (18)	N4—N3—Cu1—O1	56.36 (17)
C12—C13—C8—C9	−0.8 (3)	N4—N3—Cu1—N2	−47.4 (11)
N2—C8—C9—O1	0.8 (2)	N4—N3—Cu1—N1	−123.42 (16)
C13—C8—C9—O1	−179.90 (17)	C6—N2—Cu1—O1	−176.11 (14)
N2—C8—C9—C10	−178.59 (16)	C8—N2—Cu1—O1	−1.67 (12)
C13—C8—C9—C10	0.7 (3)	C6—N2—Cu1—N3	−72.0 (10)
C12—C11—C10—C9	−0.4 (3)	C8—N2—Cu1—N3	102.5 (10)
O1—C9—C10—C11	−179.47 (17)	C6—N2—Cu1—N1	4.61 (14)
C8—C9—C10—C11	−0.1 (3)	C8—N2—Cu1—N1	179.05 (13)
C3—C2—N1—C1	−0.6 (3)	C2—N1—Cu1—O1	177.1 (2)
C3—C2—N1—Cu1	175.50 (15)	C1—N1—Cu1—O1	−6.5 (4)
C5—C1—N1—C2	0.1 (3)	C2—N1—Cu1—N3	−3.81 (17)
C6—C1—N1—C2	178.62 (16)	C1—N1—Cu1—N3	172.56 (14)
C5—C1—N1—Cu1	−176.55 (15)	C2—N1—Cu1—N2	−179.78 (17)
C6—C1—N1—Cu1	2.0 (2)	C1—N1—Cu1—N2	−3.41 (13)
C1—C6—N2—C8	−177.73 (17)