(Azido-κN){(E)-2-[1-(pyridin-2-yl)ethyl­idene­amino]­phenolato-κ3N,N′,O}copper(II)

Datta, A.; Clegg, J.K.; Huang, J.-H.; Sheu, S.-C.

doi:10.1107/S1600536813019570

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page m468

doi:10.1107/S1600536813019570

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(Azido-κN){(E)-2-[1-(pyridin-2-yl)ethylideneamino]phenolato-κ³N,N′,O}copper(II)

Amitabha Datta,^a Jack K. Clegg,^b Jui-Hsien Huang ^a and Shiann-Cherng Sheu ^c ^*

^aDepartment of Chemistry, National Changhua University of Education, Changhua 50058, Taiwan, ^bSchool of Chemistry and Molecular Biosciences, University of Queensland, Brisbane St Lucia, Queensland 4072, Australia, and ^cDepartment of Occupational Health and Safety, Chang Jung Christian University, Tainan City 71101, Taiwan
^*Correspondence e-mail: scschem@mail.cjcu.edu.tw

(Received 2 July 2013; accepted 15 July 2013; online 20 July 2013)

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_r = 316.81
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.092
S = 1.05
2357 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813019570/lr2111sup1.cif

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

checkCIF report

Comment top

In the title complex, [Cu(C₁₃H₁₁N₂O)(N₃)], the Cu^II ion exhibits a slightly distorted square-planar coordination environment defined by the deprotonated tridentate Schiff base ligand that coordinates via the phenolate O, imine N and pyridyl N atoms and the N atom of azide ion (Fig. 1). The bond angles around Cu^II ion are slightly distorted from those of regular square-planar and range from 81.53 (7) to 175.89 (7)°. The [CuN₃O] square plane and the aryl and pyridyl rings in the Schiff base are almost coplanar. The dihedral angles among these three planes are 3.55 (6)°, 4.70 (5)° and 4.99 (7)°. The bond distances to the central copper [Cu—N_py = 1.9775 (16) Å, Cu—N_imine = 1.9682 (16) Å, Cu—N_azide = 1.9470 (18) Å, Cu—O_phenolic = 1.9133 (14) Å] (Table 1) are similar to those in complexes [Cu(C₁₄H₁₃N₂O₂)(N₃)] and [Cu(C₁₃H₁₀ClN₂O)Cl] (Sun, 2008; Wang et al., 2012). The bond distances and bond angles in azide ion bound to Cu^II ion are similar to those in complexes [Cu(C₁₄H₁₃N₂O₂)(N₃)] and [Cu(C₁₆H₂₃N₂O)(N₃)] (Sun, 2008; Talukder et al., 2004). The N3—N4 bond [1.201 (3) Å] in the complex is longer than the N4—N5 bond [1.157 (3) Å]. The NNN moiety is nearly linear and shows a bent coordination mode with the Cu^II ion [(N3—N4—N5/Cu1—N3—N4 = 177.4 (2)/117.06 (15)°].

Related literature top

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 top

The tridentate Schiff base ligand was prepared according to literature procedure (Shita et al., 2009). To a hot methanolic solution (20 ml) of Cu(CCl₃COO)₂.6H₂O (0.484 g, 1.0 mmol), the ligand (1.0 mmol) was added, which produced immediately an intensely green solution. The solution was then heated to boiling and then, an aqueous solution (10 ml) of sodium azide (0.065 g, 1 mmol) was added dropwise slowly over 15 min in hot condition. After the completion of addition of sodium azide, the resulting solution was kept under boiling for another 10 min. On cooling and after slow evaporation of the solution, the dark-green plate-shaped single crystals of the complex were separated out in 3 d. The crystals were filtered off and washed with water and dried in air.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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).

Figures top

Fig. 1. The molecular structure of the title complex, showing displacement ellipsoids at the 50% probability level.

(Azido-κN){(E)-2-[1-(pyridin-2-yl)ethylideneamino]phenolato-κ³N,N',O}copper(II) top

Crystal data top

[Cu(C₁₃H₁₁CuN₂O)(N₃)]	F(000) = 644
M_r = 316.81	D_x = 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

Data collection top

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	R_int = 0.021
Detector resolution: 16.1183 pixels mm^-1	θ_max = 72.0°, θ_min = 4.8°
ω scans	h = −8→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→12
T_min = 0.709, T_max = 1.000	l = −21→22
4723 measured reflections

Refinement top

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(F_o²) + (0.0589P)² + 0.5226P] where P = (F_o² + 2F_c²)/3
2357 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Cu(C₁₃H₁₁CuN₂O)(N₃)]	V = 1229.06 (8) Å³
M_r = 316.81	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 6.5881 (3) Å	µ = 2.54 mm⁻¹
b = 10.1576 (3) Å	T = 120 K
c = 18.3884 (7) Å	0.57 × 0.31 × 0.04 mm
β = 92.810 (3)°

Data collection top

Agilent Xcalibur Gemini ultra diffractometer with Eos detector	2357 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2180 reflections with I > 2σ(I)
T_min = 0.709, T_max = 1.000	R_int = 0.021
4723 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.05	Δρ_max = 0.34 e Å⁻³
2357 reflections	Δρ_min = −0.40 e Å⁻³
182 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[Cu(C₁₃H₁₁CuN₂O)(N₃)]
M_r	316.81
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	6.5881 (3), 10.1576 (3), 18.3884 (7)
β (°)	92.810 (3)
V (Å³)	1229.06 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.54
Crystal size (mm)	0.57 × 0.31 × 0.04

Data collection
Diffractometer	Agilent Xcalibur Gemini ultra diffractometer with Eos detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.709, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4723, 2357, 2180
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.092, 1.05
No. of reflections	2357
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.40

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and WinGX32 (Farrugia, 2012), publCIF (Westrip, 2010).

Acknowledgements

The authors are grateful to the National Science Council of Taiwan for financial support.

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