(2-{[2-Carboxyl-ato-1-(4-chloro-phen-yl)eth-yl]imino-meth-yl}phenolato-κO,N,O')(1H-imidazole-κN)copper(II) monohydrate.

The Cu(II) atom of the title complex, [Cu(C(16)H(12)ClNO(3))(C(3)H(4)N(2))]·H(2)O, has a distorted square-planar coordination geometry formed by a tridentate Schiff base dianion and an imidazole ligand. The imidazole is nearly coplanar with the coordination plane, the dihedral angle between the planes being 3.73 (12)°. In the Schiff base ligand, the two benzene rings are oriented at a dihedral angle of 75.87 (12)°. O-H⋯O and N-H⋯O hydrogen bonding is present in the crystal structure. One H atom of the uncoordinated water mol-ecule is disordered equally over two sites.

Related literature

Transition metal complexes of salicylaldehyde-peptides and salicylaldehyde-amino­acid Schiff bases are non-enzymatic models for pyridoxal amino acid systems, which are of importance as key inter­mediates in many metabolic reactions of amino acid catalyses by enzymes, see: Bkouche-Waksman et al. (1988 ▶); Wetmore et al. (2001 ▶); Zabinski & Toney (2001 ▶). For the preparation, structural characterization, appropriate spectroscopy and magnetic studies of Schiff-base complexes derived from salicylaldehyde and amino acids, see: Ganguly et al. (2008 ▶) and references cited therein. For Schiff bases derived from β-amino acids, see: Vančo et al. (2008 ▶).

Experimental

Crystal data

[Cu(C16H12ClNO3)(C3H4N2)]·H2O

M = 451.35

Monoclinic,

a = 23.884 (1) Å

b = 4.944 (1) Å

c = 32.008 (1) Å

β = 96.88 (1)°

V = 3752.4 (8) Å3

Z = 8

Mo Kα radiation

μ = 1.34 mm−1

T = 296 K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.776, T max = 0.825

18085 measured reflections

4310 independent reflections

3298 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.087

S = 1.04

4310 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810014765/xu2751sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014765/xu2751Isup2.hkl

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

[Cu(C16H12ClNO3)(C3H4N2)]·H2O	F(000) = 1848
Mr = 451.35	Dx = 1.598 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3298 reflections
a = 23.884 (1) Å	θ = 1.7–27.5°
b = 4.944 (1) Å	µ = 1.34 mm−1
c = 32.008 (1) Å	T = 296 K
β = 96.88 (1)°	Block, dark green
V = 3752.4 (8) Å3	0.20 × 0.20 × 0.15 mm
Z = 8

Bruker SMART CCD diffractometer	4310 independent reflections
Radiation source: fine-focus sealed tube	3298 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −30→30
Tmin = 0.776, Tmax = 0.825	k = −6→6
18085 measured reflections	l = −41→41

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0381P)2 + 2.3614P] where P = (Fo2 + 2Fc2)/3
4310 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Cu1	0.257392 (11)	0.70003 (6)	0.103939 (8)	0.03102 (10)
Cl1	−0.00394 (3)	1.30201 (17)	0.18252 (3)	0.0645 (2)
N1	0.20142 (7)	0.4707 (4)	0.12667 (6)	0.0301 (4)
N2	0.31243 (7)	0.9444 (4)	0.08174 (6)	0.0332 (4)
N3	0.34883 (9)	1.2624 (4)	0.04560 (7)	0.0414 (5)
H3A	0.3513	1.3915	0.0279	0.050*
O1	0.31821 (6)	0.5542 (4)	0.14014 (5)	0.0406 (4)
O2	0.13208 (7)	0.8259 (4)	0.00906 (5)	0.0425 (4)
O3	0.20152 (7)	0.8490 (4)	0.06065 (5)	0.0436 (4)
C1	0.31811 (10)	0.3666 (5)	0.16842 (7)	0.0351 (5)
C2	0.36998 (10)	0.2833 (6)	0.19110 (8)	0.0439 (6)
H2	0.4033	0.3671	0.1858	0.053*
C3	0.37183 (11)	0.0827 (6)	0.22041 (7)	0.0447 (6)
H3	0.4065	0.0316	0.2346	0.054*
C4	0.32307 (11)	−0.0477 (6)	0.22958 (8)	0.0462 (7)
H4	0.3250	−0.1838	0.2498	0.055*
C5	0.27261 (10)	0.0272 (5)	0.20854 (7)	0.0409 (6)
H5	0.2400	−0.0594	0.2146	0.049*
C6	0.26851 (10)	0.2331 (5)	0.17774 (7)	0.0329 (5)
C7	0.21439 (10)	0.2914 (5)	0.15579 (7)	0.0335 (5)
H7	0.1846	0.1879	0.1633	0.040*
C8	0.14124 (9)	0.4717 (5)	0.10794 (7)	0.0308 (5)
H8	0.1251	0.2993	0.1157	0.037*
C9	0.10709 (9)	0.6933 (5)	0.12577 (7)	0.0313 (5)
C10	0.11509 (10)	0.7554 (5)	0.16848 (8)	0.0383 (6)
H10	0.1440	0.6701	0.1857	0.046*
C11	0.08136 (10)	0.9405 (6)	0.18610 (8)	0.0433 (6)
H11	0.0875	0.9788	0.2147	0.052*
C12	0.03856 (10)	1.0673 (5)	0.16069 (8)	0.0426 (6)
C13	0.02920 (10)	1.0118 (5)	0.11820 (8)	0.0431 (6)
H13	0.0003	1.0987	0.1013	0.052*
C14	0.06307 (9)	0.8260 (5)	0.10105 (8)	0.0387 (6)
H14	0.0565	0.7881	0.0724	0.046*
C15	0.13857 (9)	0.4720 (5)	0.05973 (7)	0.0331 (5)
H15A	0.1617	0.3250	0.0513	0.040*
H15B	0.1000	0.4373	0.0477	0.040*
C16	0.15803 (9)	0.7320 (5)	0.04156 (7)	0.0325 (5)
C17	0.30207 (10)	1.1329 (5)	0.05273 (7)	0.0385 (6)
H17	0.2664	1.1707	0.0389	0.046*
C18	0.39202 (11)	1.1523 (6)	0.07154 (8)	0.0487 (7)
H18	0.4298	1.2016	0.0735	0.058*
C19	0.36968 (9)	0.9583 (6)	0.09385 (8)	0.0408 (6)
H19	0.3897	0.8504	0.1142	0.049*
O1W	0.48323 (8)	0.7498 (5)	0.01584 (7)	0.0703 (6)
H1W	0.4469	0.7337	0.0159	0.084*
H2W1	0.4959	0.8883	0.0066	0.084*	0.50
H2W2	0.4987	0.6209	0.0050	0.084*	0.50

	U11	U22	U33	U12	U13	U23
Cu1	0.02878 (15)	0.03081 (17)	0.03347 (16)	−0.00405 (12)	0.00374 (11)	0.00462 (13)
Cl1	0.0498 (4)	0.0640 (5)	0.0836 (6)	0.0023 (4)	0.0240 (4)	−0.0184 (4)
N1	0.0281 (9)	0.0298 (11)	0.0323 (10)	−0.0028 (8)	0.0034 (8)	0.0038 (9)
N2	0.0315 (10)	0.0363 (12)	0.0314 (10)	−0.0053 (9)	0.0027 (8)	0.0040 (9)
N3	0.0459 (12)	0.0394 (13)	0.0399 (11)	−0.0119 (10)	0.0094 (9)	0.0071 (10)
O1	0.0320 (8)	0.0453 (11)	0.0439 (10)	−0.0041 (8)	0.0017 (7)	0.0127 (9)
O2	0.0417 (9)	0.0455 (11)	0.0387 (9)	−0.0073 (8)	−0.0022 (8)	0.0123 (8)
O3	0.0362 (9)	0.0392 (11)	0.0525 (10)	−0.0121 (8)	−0.0064 (8)	0.0160 (9)
C1	0.0399 (13)	0.0362 (14)	0.0290 (12)	0.0020 (11)	0.0040 (10)	−0.0005 (11)
C2	0.0349 (13)	0.0546 (18)	0.0418 (14)	0.0031 (12)	0.0025 (11)	0.0028 (13)
C3	0.0447 (14)	0.0524 (17)	0.0354 (13)	0.0139 (13)	−0.0020 (11)	0.0034 (13)
C4	0.0584 (16)	0.0458 (17)	0.0340 (13)	0.0074 (14)	0.0034 (12)	0.0102 (12)
C5	0.0450 (14)	0.0396 (15)	0.0381 (13)	−0.0007 (12)	0.0050 (11)	0.0069 (12)
C6	0.0354 (12)	0.0322 (13)	0.0310 (12)	0.0030 (10)	0.0044 (9)	0.0014 (10)
C7	0.0341 (12)	0.0310 (13)	0.0364 (12)	−0.0047 (11)	0.0081 (10)	0.0022 (11)
C8	0.0276 (11)	0.0297 (12)	0.0349 (12)	−0.0080 (10)	0.0026 (9)	0.0058 (10)
C9	0.0271 (11)	0.0332 (13)	0.0340 (12)	−0.0093 (10)	0.0043 (9)	0.0028 (11)
C10	0.0343 (12)	0.0436 (16)	0.0366 (13)	−0.0048 (11)	0.0023 (10)	0.0048 (11)
C11	0.0448 (14)	0.0499 (17)	0.0359 (13)	−0.0082 (13)	0.0076 (11)	−0.0029 (13)
C12	0.0344 (12)	0.0404 (15)	0.0552 (16)	−0.0069 (12)	0.0152 (11)	−0.0048 (13)
C13	0.0293 (12)	0.0477 (16)	0.0508 (15)	−0.0029 (12)	−0.0009 (11)	0.0003 (13)
C14	0.0329 (12)	0.0457 (16)	0.0367 (13)	−0.0029 (12)	0.0003 (10)	−0.0016 (12)
C15	0.0348 (12)	0.0282 (13)	0.0355 (12)	−0.0060 (10)	0.0009 (10)	−0.0003 (11)
C16	0.0325 (11)	0.0325 (13)	0.0332 (12)	−0.0026 (10)	0.0073 (10)	0.0018 (10)
C17	0.0354 (12)	0.0422 (15)	0.0381 (13)	−0.0083 (11)	0.0046 (10)	0.0050 (12)
C18	0.0370 (13)	0.0574 (19)	0.0522 (16)	−0.0136 (13)	0.0069 (12)	0.0030 (14)
C19	0.0319 (12)	0.0470 (16)	0.0425 (14)	−0.0066 (11)	0.0004 (10)	0.0069 (12)
O1W	0.0450 (11)	0.0803 (16)	0.0830 (15)	−0.0032 (11)	−0.0032 (11)	0.0025 (12)

Cu1—O1	1.8894 (16)	C6—C7	1.425 (3)
Cu1—O3	1.9494 (16)	C7—H7	0.9300
Cu1—N1	1.9582 (18)	C8—C9	1.518 (3)
Cu1—N2	1.9789 (18)	C8—C15	1.537 (3)
Cl1—C12	1.742 (3)	C8—H8	0.9800
N1—C7	1.297 (3)	C9—C10	1.392 (3)
N1—C8	1.489 (3)	C9—C14	1.401 (3)
N2—C17	1.318 (3)	C10—C11	1.383 (3)
N2—C19	1.378 (3)	C10—H10	0.9300
N3—C17	1.331 (3)	C11—C12	1.379 (3)
N3—C18	1.358 (3)	C11—H11	0.9300
N3—H3A	0.8600	C12—C13	1.379 (3)
O1—C1	1.296 (3)	C13—C14	1.381 (3)
O2—C16	1.236 (3)	C13—H13	0.9300
O3—C16	1.278 (3)	C14—H14	0.9300
C1—C6	1.419 (3)	C15—C16	1.507 (3)
C1—C2	1.420 (3)	C15—H15A	0.9700
C2—C3	1.362 (4)	C15—H15B	0.9700
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.393 (4)	C18—C19	1.344 (3)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.360 (3)	C19—H19	0.9300
C4—H4	0.9300	O1W—H1W	0.8709
C5—C6	1.412 (3)	O1W—H2W1	0.8180
C5—H5	0.9300	O1W—H2W2	0.8325
O1—Cu1—O3	172.18 (7)	C9—C8—H8	106.6
O1—Cu1—N1	93.45 (7)	C15—C8—H8	106.6
O3—Cu1—N1	92.47 (7)	C10—C9—C14	117.2 (2)
O1—Cu1—N2	87.61 (7)	C10—C9—C8	120.8 (2)
O3—Cu1—N2	86.66 (7)	C14—C9—C8	121.8 (2)
N1—Cu1—N2	177.75 (8)	C11—C10—C9	121.9 (2)
C7—N1—C8	115.30 (18)	C11—C10—H10	119.1
C7—N1—Cu1	123.22 (15)	C9—C10—H10	119.1
C8—N1—Cu1	121.16 (14)	C12—C11—C10	119.2 (2)
C17—N2—C19	105.0 (2)	C12—C11—H11	120.4
C17—N2—Cu1	127.44 (16)	C10—C11—H11	120.4
C19—N2—Cu1	127.53 (16)	C11—C12—C13	120.8 (2)
C17—N3—C18	107.1 (2)	C11—C12—Cl1	119.5 (2)
C17—N3—H3A	126.5	C13—C12—Cl1	119.6 (2)
C18—N3—H3A	126.5	C12—C13—C14	119.4 (2)
C1—O1—Cu1	129.47 (15)	C12—C13—H13	120.3
C16—O3—Cu1	128.07 (16)	C14—C13—H13	120.3
O1—C1—C6	123.5 (2)	C13—C14—C9	121.5 (2)
O1—C1—C2	119.3 (2)	C13—C14—H14	119.2
C6—C1—C2	117.2 (2)	C9—C14—H14	119.2
C3—C2—C1	121.2 (2)	C16—C15—C8	114.26 (19)
C3—C2—H2	119.4	C16—C15—H15A	108.7
C1—C2—H2	119.4	C8—C15—H15A	108.7
C2—C3—C4	121.5 (2)	C16—C15—H15B	108.7
C2—C3—H3	119.2	C8—C15—H15B	108.7
C4—C3—H3	119.2	H15A—C15—H15B	107.6
C5—C4—C3	118.9 (2)	O2—C16—O3	122.0 (2)
C5—C4—H4	120.5	O2—C16—C15	119.9 (2)
C3—C4—H4	120.5	O3—C16—C15	118.1 (2)
C4—C5—C6	121.7 (2)	N2—C17—N3	111.7 (2)
C4—C5—H5	119.2	N2—C17—H17	124.1
C6—C5—H5	119.2	N3—C17—H17	124.1
C5—C6—C1	119.5 (2)	C19—C18—N3	106.9 (2)
C5—C6—C7	118.2 (2)	C19—C18—H18	126.6
C1—C6—C7	122.2 (2)	N3—C18—H18	126.6
N1—C7—C6	128.1 (2)	C18—C19—N2	109.3 (2)
N1—C7—H7	115.9	C18—C19—H19	125.4
C6—C7—H7	115.9	N2—C19—H19	125.4
N1—C8—C9	112.78 (18)	H1W—O1W—H2W1	119.3
N1—C8—C15	109.03 (17)	H1W—O1W—H2W2	115.1
C9—C8—C15	114.66 (19)	H2W1—O1W—H2W2	106.8
N1—C8—H8	106.6

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2i	0.87	1.98	2.799 (3)	156
O1W—H2W1···O1Wii	0.82	2.01	2.826 (4)	172
O1W—H2W2···O1Wiii	0.83	2.02	2.822 (5)	163
N3—H3A···O2iv	0.86	1.90	2.758 (3)	172

Table 1

Selected bond lengths (Å)

Cu1—O1	1.8894 (16)
Cu1—O3	1.9494 (16)
Cu1—N1	1.9582 (18)
Cu1—N2	1.9789 (18)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2i	0.87	1.98	2.799 (3)	156
O1W—H2W1⋯O1Wii	0.82	2.01	2.826 (4)	172
O1W—H2W2⋯O1Wiii	0.83	2.02	2.822 (5)	163
N3—H3A⋯O2iv	0.86	1.90	2.758 (3)	172

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .