Bis{2-[(5-hy-droxy-pent-yl)imino-meth-yl]phenolato-κ(2) N,O (1)}copper(II).

In the title compound, [Cu(C12H16NO2)2], the Cu(II) ion, located on a center of inversion, is coordinated by two singly deprotonated Schiff base ligands derived from condensation of salicyldehyde and 1-amino-pentan-5-ol. The imino N and phenol O atoms from both ligands offer a square-planar arrangement around the metal ion. The Cu-N and Cu-O bond lengths are 2.0146 (15) and 1.8870 (12) Å, respectively. Since the Cu-O and Cu-N bond lengths are different, it can be concluded that the resulting geometry of the complex is distorted. The aliphatic -OH group of the ligand is not coordinated and points away from the metal coordination zone and actively participates in hydrogen bonding connecting two other units and thus stabilizing the crystal lattice. This results in a two-dimensional extended array parallel to (201).

Related literature

For the participation of the copper ion in the active sites of a large number of metalloproteins involved in important biological electron-transfer reactions, see: Reedijk & Bouwman (1999 ▶); Solomon et al. (2001 ▶); Hatcher & Karlin (2004 ▶); Kaim & Rall (1996 ▶). For references regarding the t4 value, see: Yang et al. (2007 ▶). For similar Cu—N and Cu—O bond lengths, see: Maeda et al. (2003 ▶); Akimova et al. (2001 ▶); Pawlicki et al. (2007 ▶); Verma et al. (2011 ▶); Khandar & Nejati (2000 ▶); Sundaravel et al. (2009 ▶).

Experimental

Crystal data

[Cu(C12H16NO2)2]

M = 476.07

Monoclinic,

a = 11.8815 (8) Å

b = 5.2219 (3) Å

c = 18.9588 (12) Å

β = 102.876 (2)°

V = 1146.70 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.99 mm−1

T = 296 K

0.8 × 0.6 × 0.4 mm

Data collection

Bruker APEXII SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.497, T max = 0.674

13343 measured reflections

2549 independent reflections

2174 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.096

S = 0.95

2549 reflections

143 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: Mercury (Macrae et al., 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016802/bv2221sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016802/bv2221Isup2.hkl

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

[Cu(C12H16NO2)2]	F(000) = 502.0
Mr = 476.07	Dx = 1.385 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13343 reflections
a = 11.8815 (8) Å	θ = 1.8–27.5°
b = 5.2219 (3) Å	µ = 0.99 mm−1
c = 18.9588 (12) Å	T = 296 K
β = 102.876 (2)°	Block, dark green
V = 1146.70 (12) Å3	0.8 × 0.6 × 0.4 mm
Z = 2

Bruker APEXII SMART CCD diffractometer	2549 independent reflections
Radiation source: fine-focus sealed tube	2174 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.497, Tmax = 0.674	k = −6→6
13343 measured reflections	l = −24→24

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0695P)2 + 0.3017P] where P = (Fo2 + 2Fc2)/3
2549 reflections	(Δ/σ)max = 0.015
143 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.30 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	1.0000	0.5000	0.5000	0.03217 (12)
O1	0.50800 (15)	0.8210 (3)	0.72046 (8)	0.0640 (4)
H1	0.4971	0.9476	0.7436	0.096*
O2	1.04519 (10)	0.2230 (2)	0.44865 (7)	0.0440 (3)
N1	0.83417 (13)	0.4686 (3)	0.44597 (8)	0.0338 (3)
C1	0.74512 (14)	0.6417 (3)	0.46237 (9)	0.0372 (4)
H1A	0.6794	0.6453	0.4215	0.045*
H1B	0.7761	0.8140	0.4697	0.045*
C2	0.70561 (16)	0.5564 (3)	0.52942 (10)	0.0389 (4)
H2A	0.6628	0.3975	0.5191	0.047*
H2B	0.7727	0.5236	0.5680	0.047*
C3	0.63016 (16)	0.7546 (4)	0.55460 (10)	0.0420 (4)
H3A	0.5621	0.7829	0.5163	0.050*
H3B	0.6722	0.9150	0.5629	0.050*
C4	0.59209 (16)	0.6804 (4)	0.62336 (10)	0.0422 (4)
H4A	0.5346	0.5457	0.6122	0.051*
H4B	0.6579	0.6127	0.6581	0.051*
C5	0.5428 (2)	0.8995 (5)	0.65661 (12)	0.0571 (5)
H5A	0.6001	1.0342	0.6685	0.068*
H5B	0.4768	0.9679	0.6222	0.068*
C6	0.79987 (14)	0.3133 (3)	0.39297 (9)	0.0375 (4)
H6	0.7230	0.3277	0.3687	0.045*
C7	0.86641 (14)	0.1202 (3)	0.36685 (8)	0.0362 (4)
C8	0.98489 (15)	0.0831 (3)	0.39729 (9)	0.0357 (3)
C9	1.04061 (17)	−0.1203 (3)	0.36855 (10)	0.0437 (4)
H9	1.1187	−0.1500	0.3873	0.052*
C10	0.98222 (18)	−0.2730 (4)	0.31404 (10)	0.0485 (5)
H10	1.0212	−0.4049	0.2967	0.058*
C11	0.86595 (19)	−0.2348 (4)	0.28419 (10)	0.0502 (5)
H11	0.8270	−0.3392	0.2469	0.060*
C12	0.80936 (19)	−0.0411 (4)	0.31035 (11)	0.0452 (4)
H12	0.7313	−0.0149	0.2904	0.054*

	U11	U22	U33	U12	U13	U23
Cu1	0.02804 (18)	0.03330 (18)	0.03728 (18)	0.00376 (10)	0.01180 (12)	−0.00224 (10)
O1	0.0847 (11)	0.0657 (9)	0.0553 (8)	0.0084 (8)	0.0448 (8)	0.0046 (7)
O2	0.0337 (6)	0.0444 (7)	0.0535 (7)	0.0065 (5)	0.0088 (5)	−0.0123 (6)
N1	0.0299 (7)	0.0393 (8)	0.0358 (7)	0.0058 (5)	0.0146 (6)	0.0026 (5)
C1	0.0309 (8)	0.0425 (9)	0.0405 (8)	0.0106 (7)	0.0131 (6)	0.0037 (7)
C2	0.0356 (9)	0.0362 (8)	0.0498 (10)	0.0068 (7)	0.0203 (7)	0.0052 (7)
C3	0.0427 (9)	0.0422 (9)	0.0471 (9)	0.0112 (7)	0.0226 (8)	0.0079 (7)
C4	0.0442 (10)	0.0426 (9)	0.0444 (9)	0.0038 (7)	0.0198 (7)	0.0042 (7)
C5	0.0746 (15)	0.0529 (12)	0.0562 (12)	0.0147 (11)	0.0415 (11)	0.0116 (10)
C6	0.0312 (8)	0.0467 (9)	0.0359 (8)	0.0016 (7)	0.0103 (6)	0.0029 (7)
C7	0.0402 (9)	0.0369 (9)	0.0350 (8)	−0.0010 (7)	0.0158 (7)	0.0006 (7)
C8	0.0400 (9)	0.0318 (8)	0.0386 (8)	0.0028 (7)	0.0161 (7)	0.0015 (7)
C9	0.0481 (10)	0.0371 (9)	0.0486 (10)	0.0099 (8)	0.0167 (8)	−0.0001 (8)
C10	0.0693 (13)	0.0356 (9)	0.0464 (10)	0.0071 (9)	0.0252 (9)	−0.0032 (8)
C11	0.0651 (13)	0.0474 (10)	0.0399 (9)	−0.0069 (9)	0.0156 (8)	−0.0066 (8)
C12	0.0459 (11)	0.0537 (11)	0.0369 (9)	−0.0038 (8)	0.0110 (8)	−0.0025 (7)

Cu1—O2i	1.8870 (12)	C4—C5	1.488 (3)
Cu1—O2	1.8870 (12)	C4—H4A	0.9700
Cu1—N1i	2.0146 (15)	C4—H4B	0.9700
Cu1—N1	2.0146 (15)	C5—H5A	0.9700
O1—C5	1.424 (2)	C5—H5B	0.9700
O1—H1	0.8200	C6—C7	1.436 (2)
O2—C8	1.298 (2)	C6—H6	0.9300
N1—C6	1.285 (2)	C7—C8	1.411 (2)
N1—C1	1.476 (2)	C7—C12	1.411 (3)
C1—C2	1.517 (2)	C8—C9	1.423 (2)
C1—H1A	0.9700	C9—C10	1.366 (3)
C1—H1B	0.9700	C9—H9	0.9300
C2—C3	1.514 (2)	C10—C11	1.386 (3)
C2—H2A	0.9700	C10—H10	0.9300
C2—H2B	0.9700	C11—C12	1.368 (3)
C3—C4	1.522 (2)	C11—H11	0.9300
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700
O2i—Cu1—O2	179.999 (1)	C3—C4—H4A	109.0
O2i—Cu1—N1i	91.94 (5)	C5—C4—H4B	109.0
O2—Cu1—N1i	88.06 (5)	C3—C4—H4B	109.0
O2i—Cu1—N1	88.06 (5)	H4A—C4—H4B	107.8
O2—Cu1—N1	91.94 (5)	O1—C5—C4	110.77 (17)
N1i—Cu1—N1	179.998 (1)	O1—C5—H5A	109.5
C5—O1—H1	109.5	C4—C5—H5A	109.5
C8—O2—Cu1	130.21 (11)	O1—C5—H5B	109.5
C6—N1—C1	115.71 (15)	C4—C5—H5B	109.5
C6—N1—Cu1	123.56 (12)	H5A—C5—H5B	108.1
C1—N1—Cu1	120.58 (11)	N1—C6—C7	127.59 (15)
N1—C1—C2	111.53 (13)	N1—C6—H6	116.2
N1—C1—H1A	109.3	C7—C6—H6	116.2
C2—C1—H1A	109.3	C8—C7—C12	119.69 (16)
N1—C1—H1B	109.3	C8—C7—C6	122.08 (15)
C2—C1—H1B	109.3	C12—C7—C6	118.20 (16)
H1A—C1—H1B	108.0	O2—C8—C7	124.29 (15)
C3—C2—C1	112.27 (14)	O2—C8—C9	118.78 (16)
C3—C2—H2A	109.2	C7—C8—C9	116.92 (16)
C1—C2—H2A	109.2	C10—C9—C8	121.64 (18)
C3—C2—H2B	109.2	C10—C9—H9	119.2
C1—C2—H2B	109.2	C8—C9—H9	119.2
H2A—C2—H2B	107.9	C9—C10—C11	121.12 (17)
C2—C3—C4	113.92 (15)	C9—C10—H10	119.4
C2—C3—H3A	108.8	C11—C10—H10	119.4
C4—C3—H3A	108.8	C12—C11—C10	118.98 (18)
C2—C3—H3B	108.8	C12—C11—H11	120.5
C4—C3—H3B	108.8	C10—C11—H11	120.5
H3A—C3—H3B	107.7	C11—C12—C7	121.66 (19)
C5—C4—C3	112.76 (15)	C11—C12—H12	119.2
C5—C4—H4A	109.0	C7—C12—H12	119.2

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1ii	0.82	2.07	2.864 (2)	163
C1—H1B···O2i	0.97	2.34	2.771 (2)	106

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1i	0.82	2.07	2.864 (2)	163
C1—H1B⋯O2ii	0.97	2.34	2.771 (2)	106

Symmetry codes: (i) ; (ii) .