Aqua­{N-[1-(2-oxidophen­yl)ethyl­idene]-l-serinato}copper(II) monohydrate

Zhao, G.-Q.; Tian, D.-M.; Han, Y.-J.; Xue, L.-W.; Peng, Q.-L.

doi:10.1107/S1600536809045292

metal-organic compounds

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Volume 65| Part 12| December 2009| Page m1505

doi:10.1107/S1600536809045292

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Aqua{N-[1-(2-oxidophenyl)ethylidene]-L-serinato}copper(II) monohydrate

Gan-Qing Zhao,^a ^* Da-Ming Tian,^b Yong-Jun Han,^a Ling-Wei Xue ^a and Qin-Long Peng ^a

^aSchool of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan 467000, People's Republic of China, and ^bDepartment of Chemical Engineering, Henan University of Urban Construction, Pingdingshan 467044, People's Republic of China
^*Correspondence e-mail: zgq1118@163.com

(Received 23 October 2009; accepted 29 October 2009; online 4 November 2009)

In the title compound, [Cu(C₁₁H₁₁NO₄)(H₂O)]·H₂O, 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 molecule in a distorted square-planar geometry. Intermolecular O—H⋯O hydrogen bonds link complex molecules and solvent water molecules 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_r = 320.78
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.022
wR(F²) = 0.053
S = 1.09
2149 reflections
176 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 869 Friedel pairs
Flack parameter: 0.011 (13)

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⋯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
Symmetry codes: (i) x+1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

In the past decades, significant progress has been achieved in understanding the chemistry of transition metal complexes with Schiff base ligands composed of salicylaldehyde, 2-formylpyridine or their analogues, and α-amino acids (Vigato & Tamburini, 2004; Ganguly et al., 2008; Casella & Guillotti, 1983). A few stuctural studies have been performed on Schiff base complexes derived from 2-Hydroxyacetophenone and animo acids (Usman et al., 2003; Basu Baul et al., 2007; Parekh et al., 2006). We report here the crystal structure of the title compound (I).

The asymmetric unit of (I) contains a monomeric square-planar coordinated Cu^II complex and one solvate water molecule (Fig. 1). The Cu—N bond length is 1.9335 (19) Å, while Cu—O bond lengths lie in the range 1.8595 (18)-1.9677 (18) Å.

The crystal structure is stabilized by O—H···O type hydrogen bonds (Table 1), which link complex molecules and solvent water molecules into flattened columns propagated in direction [100].

Related literature top

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 top

The title compound was synthesized as described in the literature (Plesch et al., 1997). To L-serine (1.00 mmol) and potassium hydroxide (1.00 mmol) in 10 ml of methanol was added 2-Hydroxyacetophenone (1.00 mmol in 10 ml of methanol) dropwise. The yellow solution was stirred for 2.0 h at 333 K. The resultant mixture was added dropwise to copper (II) acetate monohydrate (1.00 mmol) in an aqueous methanolic solution (20 ml, 1:1 v/v), and heated with stirring for 2.0 h at 333 K. The dark green solution was filtered and left for several days, dark green crystals had formed that were filtered off, washed with water, and dried under vacuum.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Aqua{N-[1-(2-oxidophenyl)ethylidene]-L-serinato}copper(II) monohydrate top

Crystal data top

[Cu(C₁₁H₁₁NO₄)(H₂O)]·H₂O	F(000) = 660
M_r = 320.78	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0174P)² + 0.2008P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.053	(Δ/σ)_max = 0.001
S = 1.09	Δρ_max = 0.21 e Å⁻³
2149 reflections	Δρ_min = −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	Absolute structure parameter: 0.011 (13)

Crystal data top

[Cu(C₁₁H₁₁NO₄)(H₂O)]·H₂O	V = 1214.6 (3) Å³
M_r = 320.78	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.6701 (9) Å	µ = 1.82 mm⁻¹
b = 13.788 (2) Å	T = 296 K
c = 15.536 (2) Å	0.25 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2149 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2038 reflections with I > 2σ(I)
T_min = 0.659, T_max = 0.712	R_int = 0.027
6314 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.053	Δρ_max = 0.21 e Å⁻³
S = 1.09	Δρ_min = −0.24 e Å⁻³
2149 reflections	Absolute structure: Flack (1983), 869 Friedel pairs
176 parameters	Absolute structure parameter: 0.011 (13)
0 restraints

Special details top

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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₁H₁₁NO₄)(H₂O)]·H₂O
M_r	320.78
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	5.6701 (9), 13.788 (2), 15.536 (2)
V (Å³)	1214.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.82
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.659, 0.712
No. of measured, independent and observed [I > 2σ(I)] reflections	6314, 2149, 2038
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.053, 1.09
No. of reflections	2149
No. of parameters	176
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.24
Absolute structure	Flack (1983), 869 Friedel pairs
Absolute structure parameter	0.011 (13)

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3ⁱ	0.82	1.84	2.651 (3)	170.9
O1W—H1WA···O2Wⁱⁱ	0.82	1.91	2.694 (3)	160.7
O1W—H1WB···O2ⁱⁱⁱ	0.85	1.92	2.740 (3)	161.9
O2W—H2WA···O4	0.85	2.04	2.837 (3)	155.7
O2W—H2WB···O1ⁱⁱ	0.85	2.02	2.817 (3)	156.6

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1/2, −y+1/2, −z+1.

Acknowledgements

This research was supported by the National Sciences Foundation of China (grant No. 20877036) and High-Level Personnel Foundation of Pingdingshan University (grant No. 2009001).

References

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