Aqua-{N-[1-(2-oxidophen-yl)ethyl-idene]-l-serinato}copper(II) monohydrate.

In the title compound, [Cu(C(11)H(11)NO(4))(H(2)O)]·H(2)O, each Cu(II) ion is four-coordinated by one N and two O atoms from the tridentate Schiff base ligand, and by one O atom from the coordinated water mol-ecule in a distorted square-planar geometry. Inter-molecular O-H⋯O hydrogen bonds link complex mol-ecules and solvent water mol-ecules into flattened columns propagated in [100].

Related literature

For general background to the chemistry of transition metal complexes with Schiff base ligands composed of salicylaldehyde, 2-formyl­pyridine or their analogues, and α-amino acids, see: Casella & Guillotti (1983 ▶); Vigato & Tamburini (2004 ▶); Ganguly et al. (2008 ▶). For related structures, see: Usman et al. (2003 ▶); Parekh et al. (2006 ▶); Basu Baul et al. (2007 ▶). For details of the synthesis, see: Plesch et al. (1997 ▶).

Experimental

Crystal data

[Cu(C11H11NO4)(H2O)]·H2O

M = 320.78

Orthorhombic,

a = 5.6701 (9) Å

b = 13.788 (2) Å

c = 15.536 (2) Å

V = 1214.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.82 mm−1

T = 296 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.659, T max = 0.712

6314 measured reflections

2149 independent reflections

2038 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.053

S = 1.09

2149 reflections

176 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 869 Friedel pairs

Flack parameter: 0.011 (13)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045292/cv2643sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045292/cv2643Isup2.hkl

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

[Cu(C11H11NO4)(H2O)]·H2O	F(000) = 660
Mr = 320.78	Dx = 1.754 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3823 reflections
a = 5.6701 (9) Å	θ = 2.6–27.3°
b = 13.788 (2) Å	µ = 1.82 mm−1
c = 15.536 (2) Å	T = 296 K
V = 1214.6 (3) Å3	Block, dark green
Z = 4	0.25 × 0.20 × 0.20 mm

Bruker SMART APEXII CCD diffractometer	2149 independent reflections
Radiation source: fine-focus sealed tube	2038 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −2→6
Tmin = 0.659, Tmax = 0.712	k = −16→16
6314 measured reflections	l = −18→18

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.022	w = 1/[σ2(Fo2) + (0.0174P)2 + 0.2008P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.053	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.21 e Å−3
2149 reflections	Δρmin = −0.24 e Å−3
176 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0120 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 869 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.011 (13)

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	0.18718 (6)	0.09862 (2)	0.532935 (19)	0.02947 (11)
C1	0.5839 (5)	−0.02296 (17)	0.50130 (16)	0.0286 (6)
C2	0.7793 (5)	−0.04620 (19)	0.44924 (16)	0.0378 (7)
H2	0.8084	−0.0092	0.4003	0.045*
C3	0.9287 (5)	−0.12205 (18)	0.46860 (19)	0.0390 (6)
H3	1.0554	−0.1360	0.4326	0.047*
C4	0.8899 (5)	−0.17732 (19)	0.54164 (19)	0.0382 (7)
H4	0.9903	−0.2284	0.5553	0.046*
C5	0.7019 (6)	−0.15591 (18)	0.59347 (16)	0.0340 (6)
H5	0.6780	−0.1933	0.6425	0.041*
C6	0.5428 (5)	−0.07988 (16)	0.57613 (15)	0.0268 (6)
C7	0.3496 (5)	−0.06175 (17)	0.63784 (15)	0.0283 (6)
C8	0.0332 (5)	0.03559 (19)	0.69616 (16)	0.0304 (6)
H8	−0.0484	−0.0238	0.7139	0.036*
C9	−0.1447 (4)	0.10765 (19)	0.66029 (18)	0.0354 (6)
C10	0.3232 (7)	−0.1327 (2)	0.71079 (18)	0.0469 (8)
H10A	0.4539	−0.1260	0.7496	0.070*
H10B	0.3200	−0.1976	0.6883	0.070*
H10C	0.1788	−0.1199	0.7410	0.070*
C11	0.1466 (5)	0.0833 (2)	0.77456 (16)	0.0393 (7)
H11A	0.0281	0.0931	0.8187	0.047*
H11B	0.2671	0.0408	0.7978	0.047*
N1	0.2116 (4)	0.01209 (14)	0.63046 (12)	0.0247 (4)
O1	0.4525 (3)	0.05113 (12)	0.47659 (11)	0.0372 (4)
O2	−0.0953 (4)	0.14741 (13)	0.58792 (13)	0.0409 (5)
O3	−0.3178 (4)	0.12658 (15)	0.70381 (15)	0.0552 (6)
O4	0.2492 (3)	0.17369 (14)	0.75275 (13)	0.0412 (5)
H4A	0.3869	0.1654	0.7383	0.062*
O1W	0.1373 (4)	0.18950 (14)	0.43700 (13)	0.0523 (6)
H1WA	−0.0026	0.1897	0.4236	0.078*
H1WB	0.1923	0.2466	0.4318	0.078*
O2W	0.2141 (4)	0.33399 (16)	0.63903 (14)	0.0550 (6)
H2WA	0.2036	0.2776	0.6607	0.066*
H2WB	0.1045	0.3569	0.6077	0.066*

	U11	U22	U33	U12	U13	U23
Cu1	0.02747 (17)	0.02884 (16)	0.03211 (16)	0.00077 (15)	−0.00322 (15)	0.00440 (13)
C1	0.0274 (14)	0.0282 (12)	0.0303 (12)	−0.0033 (11)	−0.0041 (12)	−0.0019 (11)
C2	0.0400 (17)	0.0408 (15)	0.0324 (14)	−0.0022 (13)	0.0062 (13)	−0.0010 (11)
C3	0.0339 (15)	0.0387 (15)	0.0446 (15)	0.0005 (12)	0.0076 (15)	−0.0103 (13)
C4	0.0327 (15)	0.0318 (13)	0.0500 (17)	0.0059 (12)	−0.0027 (14)	−0.0036 (14)
C5	0.0379 (15)	0.0273 (12)	0.0368 (14)	0.0001 (14)	−0.0022 (15)	−0.0017 (11)
C6	0.0254 (13)	0.0248 (13)	0.0302 (12)	−0.0027 (11)	−0.0013 (11)	−0.0041 (10)
C7	0.0267 (15)	0.0286 (12)	0.0296 (12)	−0.0029 (11)	−0.0028 (12)	0.0015 (10)
C8	0.0228 (14)	0.0329 (13)	0.0354 (14)	−0.0055 (12)	0.0067 (12)	0.0012 (11)
C9	0.0238 (15)	0.0309 (13)	0.0517 (16)	−0.0047 (13)	−0.0008 (13)	−0.0103 (14)
C10	0.0446 (19)	0.0500 (16)	0.0459 (16)	0.0087 (16)	0.0081 (17)	0.0212 (13)
C11	0.0340 (17)	0.0547 (17)	0.0291 (12)	−0.0025 (14)	0.0084 (12)	−0.0040 (13)
N1	0.0224 (11)	0.0263 (10)	0.0254 (10)	−0.0043 (10)	−0.0002 (10)	−0.0010 (8)
O1	0.0353 (10)	0.0426 (10)	0.0336 (10)	0.0061 (9)	0.0052 (9)	0.0097 (8)
O2	0.0347 (11)	0.0372 (10)	0.0509 (12)	0.0099 (9)	−0.0037 (10)	0.0023 (9)
O3	0.0287 (12)	0.0614 (14)	0.0754 (15)	0.0059 (11)	0.0118 (13)	−0.0107 (11)
O4	0.0291 (13)	0.0436 (10)	0.0508 (12)	−0.0034 (8)	0.0022 (9)	−0.0159 (9)
O1W	0.0461 (15)	0.0468 (12)	0.0639 (13)	−0.0085 (10)	−0.0166 (11)	0.0273 (11)
O2W	0.0374 (12)	0.0585 (13)	0.0690 (14)	−0.0080 (12)	−0.0080 (12)	0.0245 (11)

Cu1—O1	1.8595 (18)	C8—N1	1.473 (3)
Cu1—N1	1.9335 (19)	C8—C9	1.522 (4)
Cu1—O2	1.936 (2)	C8—C11	1.527 (4)
Cu1—O1W	1.9677 (18)	C8—H8	0.9800
C1—O1	1.322 (3)	C9—O3	1.220 (3)
C1—C2	1.408 (4)	C9—O2	1.282 (3)
C1—C6	1.422 (3)	C10—H10A	0.9600
C2—C3	1.379 (4)	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C3—C4	1.385 (4)	C11—O4	1.416 (3)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.368 (4)	C11—H11B	0.9700
C4—H4	0.9300	O4—H4A	0.8200
C5—C6	1.409 (4)	O1W—H1WA	0.8200
C5—H5	0.9300	O1W—H1WB	0.8502
C6—C7	1.477 (3)	O2W—H2WA	0.8500
C7—N1	1.289 (3)	O2W—H2WB	0.8500
C7—C10	1.505 (3)
O1—Cu1—N1	95.37 (8)	C9—C8—C11	106.9 (2)
O1—Cu1—O2	177.99 (9)	N1—C8—H8	109.6
N1—Cu1—O2	85.87 (9)	C9—C8—H8	109.6
O1—Cu1—O1W	89.08 (9)	C11—C8—H8	109.6
N1—Cu1—O1W	175.46 (9)	O3—C9—O2	124.8 (3)
O2—Cu1—O1W	89.66 (9)	O3—C9—C8	118.0 (3)
O1—C1—C2	116.9 (2)	O2—C9—C8	117.1 (2)
O1—C1—C6	124.9 (2)	C7—C10—H10A	109.5
C2—C1—C6	118.2 (2)	C7—C10—H10B	109.5
C3—C2—C1	122.0 (2)	H10A—C10—H10B	109.5
C3—C2—H2	119.0	C7—C10—H10C	109.5
C1—C2—H2	119.0	H10A—C10—H10C	109.5
C2—C3—C4	119.9 (3)	H10B—C10—H10C	109.5
C2—C3—H3	120.1	O4—C11—C8	111.2 (2)
C4—C3—H3	120.1	O4—C11—H11A	109.4
C5—C4—C3	119.2 (2)	C8—C11—H11A	109.4
C5—C4—H4	120.4	O4—C11—H11B	109.4
C3—C4—H4	120.4	C8—C11—H11B	109.4
C4—C5—C6	123.1 (2)	H11A—C11—H11B	108.0
C4—C5—H5	118.4	C7—N1—C8	121.9 (2)
C6—C5—H5	118.4	C7—N1—Cu1	126.91 (17)
C5—C6—C1	117.5 (2)	C8—N1—Cu1	110.98 (15)
C5—C6—C7	118.5 (2)	C1—O1—Cu1	126.28 (16)
C1—C6—C7	124.0 (2)	C9—O2—Cu1	114.80 (17)
N1—C7—C6	121.7 (2)	C11—O4—H4A	109.5
N1—C7—C10	121.3 (2)	Cu1—O1W—H1WA	109.5
C6—C7—C10	116.9 (2)	Cu1—O1W—H1WB	127.5
N1—C8—C9	110.2 (2)	H1WA—O1W—H1WB	109.1
N1—C8—C11	111.0 (2)	H2WA—O2W—H2WB	121.1

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3i	0.82	1.84	2.651 (3)	171
O1W—H1WA···O2Wii	0.82	1.91	2.694 (3)	161
O1W—H1WB···O2iii	0.85	1.92	2.740 (3)	162
O2W—H2WA···O4	0.85	2.04	2.837 (3)	156
O2W—H2WB···O1ii	0.85	2.02	2.817 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O3i	0.82	1.84	2.651 (3)	171
O1W—H1WA⋯O2W ii	0.82	1.91	2.694 (3)	161
O1W—H1WB⋯O2iii	0.85	1.92	2.740 (3)	162
O2W—H2WA⋯O4	0.85	2.04	2.837 (3)	156
O2W—H2WB⋯O1ii	0.85	2.02	2.817 (3)	157

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