catena-Poly[[pyridinecopper(II)]-μ-N-[(2-oxido-1-naphth­yl)methyl­ene]glycinato]

Xue, L.-W.; Li, X.-W.; Zhao, G.-Q.; Peng, Q.-L.

doi:10.1107/S1600536809037520

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1237

doi:10.1107/S1600536809037520

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catena-Poly[[pyridinecopper(II)]-μ-N-[(2-oxido-1-naphthyl)methylene]glycinato]

Ling-Wei Xue,^a ^* Xing-Wu Li,^a Gan-Qing Zhao ^a and Qin-Long Peng ^a

^aSchool of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan 467000, People's Republic of China
^*Correspondence e-mail: xlingwei@163.com

(Received 13 August 2009; accepted 16 September 2009; online 26 September 2009)

In the title compound, [Cu(C₁₃H₉NO₃)(C₅H₅N)], the Cu^II atom is coordinated in a distorted square-pyramidal geometry, with two N and two O atoms in the basal positions and one O atom in the apical position. The apical Cu—O bond [2.3520 (16) Å] is much longer than the basal Cu—O and Cu—N bonds [1.9139 (14)–2.0136 (17) Å]. The carboxylate group bridges Cu^II atoms, forming a zigzag chain along the a axis.

Related literature

For related structures, see: Basu Baul et al. (2007 ); Parekh et al. (2006 ); Usman et al. (2003 ); Vigato & Tamburini (2004 ); Casella & Gullotti (1983 ).

Experimental

Crystal data

[Cu(C₁₃H₉NO₃)(C₅H₅N)]
M_r = 369.85
Monoclinic, P 2₁ /c
a = 14.508 (4) Å
b = 11.747 (3) Å
c = 9.407 (3) Å
β = 101.805 (3)°
V = 1569.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.41 mm⁻¹
T = 296 K
0.30 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.662, T_max = 0.703
7938 measured reflections
2770 independent reflections
2460 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.069
S = 1.04
2770 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.9139 (14)
Cu1—N1	1.9296 (17)
Cu1—O2	1.9702 (14)
Cu1—N2	2.0136 (17)
Cu1—O3ⁱ	2.3520 (16)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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/S1600536809037520/is2450sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037520/is2450Isup2.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; Casella & Gullotti, 1983). A few structural 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 Cu^II complex, (I).

The structure consists of a square pyramidal Cu^II complex (Fig. 1 and Table 1). The four basal positions are occupied by three donor atoms from the tridentate Schiff base ligand, which furnishes an ONO donor set, with the fourth position occupied by one N atom from the pyridine ligand. The fifth position is occupied by one O atom from the adjacent tridentate Schiff base ligand.

The crystal structure is stabilized by the long-distance coordination of Cu1 and O3 (Fig. 2 and Table 2). The distance of Cu1—O3 bonds is 2.3520 (16) Å, and the distance of the two Cu(II) atoms is 6.013 Å.

Related literature top

For related structures, see: Basu Baul et al. (2007); Parekh et al. (2006); Usman et al. (2003); Vigato & Tamburini (2004); Casella & Gullotti (1983).

Experimental top

The title compound was synthesized as described in the literature. To glycine (1.00 mmol) and potassium hydroxide (1.00 mmol) in 10 ml of methanol and 5 ml of water was added 2-hydroxy-1-naphthaldehyde (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 Cu(II) nitrate hexahydrate (1.00 mmol) and pyridine (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 brown solution was filtered and left for several days, brown crystals had formed that were filtered off, washed with water, and dried under vacuum.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view of the crystal packing along the c axis.

catena-Poly[[pyridinecopper(II)]-µ-N- [(2-oxido-1-naphthyl)methylene]glycinato] top

Crystal data top

[Cu(C₁₃H₉NO₃)(C₅H₅N)]	F(000) = 756
M_r = 369.85	D_x = 1.565 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4385 reflections
a = 14.508 (4) Å	θ = 2.3–27.5°
b = 11.747 (3) Å	µ = 1.41 mm⁻¹
c = 9.407 (3) Å	T = 296 K
β = 101.805 (3)°	Block, brown
V = 1569.5 (8) Å³	0.30 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2770 independent reflections
Radiation source: fine-focus sealed tube	2460 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→17
T_min = 0.662, T_max = 0.703	k = −13→13
7938 measured reflections	l = −10→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.0336P)² + 0.6894P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2770 reflections	Δρ_max = 0.26 e Å⁻³
218 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0072 (6)

Crystal data top

[Cu(C₁₃H₉NO₃)(C₅H₅N)]	V = 1569.5 (8) Å³
M_r = 369.85	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.508 (4) Å	µ = 1.41 mm⁻¹
b = 11.747 (3) Å	T = 296 K
c = 9.407 (3) Å	0.30 × 0.30 × 0.25 mm
β = 101.805 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2770 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2460 reflections with I > 2σ(I)
T_min = 0.662, T_max = 0.703	R_int = 0.018
7938 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.04	Δρ_max = 0.26 e Å⁻³
2770 reflections	Δρ_min = −0.23 e Å⁻³
218 parameters

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	0.754799 (16)	0.40947 (2)	0.14007 (3)	0.03547 (11)
C1	0.58094 (14)	0.47447 (17)	0.2269 (2)	0.0363 (5)
C2	0.53738 (17)	0.5434 (2)	0.3195 (3)	0.0499 (6)
H2	0.5734	0.5967	0.3797	0.060*
C3	0.44485 (18)	0.5327 (2)	0.3216 (3)	0.0555 (6)
H3	0.4194	0.5774	0.3855	0.067*
C4	0.38571 (16)	0.4559 (2)	0.2299 (3)	0.0468 (6)
C5	0.28967 (18)	0.4444 (3)	0.2361 (3)	0.0638 (7)
H5	0.2657	0.4864	0.3041	0.077*
C6	0.23200 (19)	0.3736 (3)	0.1457 (4)	0.0716 (8)
H6	0.1693	0.3659	0.1525	0.086*
C7	0.26763 (17)	0.3122 (2)	0.0417 (3)	0.0645 (7)
H7	0.2279	0.2647	−0.0224	0.077*
C8	0.36069 (15)	0.3211 (2)	0.0331 (3)	0.0494 (6)
H8	0.3827	0.2801	−0.0378	0.059*
C9	0.42367 (15)	0.39105 (17)	0.1292 (2)	0.0389 (5)
C10	0.52409 (14)	0.39925 (16)	0.1297 (2)	0.0335 (4)
C11	0.56303 (14)	0.33185 (17)	0.0311 (2)	0.0354 (5)
H11	0.5214	0.2884	−0.0357	0.042*
C12	0.68024 (15)	0.25177 (19)	−0.0810 (2)	0.0436 (5)
H12A	0.6376	0.2612	−0.1742	0.052*
H12B	0.6775	0.1729	−0.0515	0.052*
C13	0.77987 (14)	0.28074 (17)	−0.0955 (2)	0.0358 (5)
C14	0.93488 (18)	0.5307 (3)	0.1688 (3)	0.0643 (7)
H14	0.9353	0.4959	0.0802	0.077*
C15	1.0076 (2)	0.6014 (3)	0.2262 (4)	0.0809 (10)
H15	1.0560	0.6146	0.1768	0.097*
C16	1.00878 (19)	0.6523 (3)	0.3557 (4)	0.0771 (9)
H16	1.0572	0.7017	0.3957	0.093*
C17	0.9372 (2)	0.6294 (3)	0.4269 (4)	0.0774 (9)
H17	0.9371	0.6613	0.5173	0.093*
C18	0.86512 (17)	0.5579 (2)	0.3615 (3)	0.0601 (7)
H18	0.8161	0.5436	0.4090	0.072*
N1	0.65107 (11)	0.32565 (14)	0.02613 (18)	0.0353 (4)
N2	0.86312 (12)	0.50919 (16)	0.2340 (2)	0.0424 (4)
O1	0.67150 (10)	0.48556 (12)	0.24244 (16)	0.0414 (3)
O2	0.82497 (9)	0.34878 (13)	−0.00179 (15)	0.0400 (3)
O3	0.81199 (11)	0.23568 (14)	−0.19287 (17)	0.0514 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03099 (16)	0.03984 (17)	0.03662 (17)	−0.00672 (10)	0.00934 (11)	−0.00578 (11)
C1	0.0389 (12)	0.0339 (11)	0.0372 (11)	0.0025 (9)	0.0102 (9)	0.0061 (9)
C2	0.0500 (14)	0.0490 (14)	0.0523 (14)	0.0021 (11)	0.0147 (11)	−0.0094 (11)
C3	0.0544 (15)	0.0599 (15)	0.0579 (16)	0.0146 (12)	0.0247 (12)	−0.0053 (13)
C4	0.0391 (12)	0.0486 (13)	0.0557 (14)	0.0110 (11)	0.0164 (11)	0.0125 (11)
C5	0.0460 (15)	0.0705 (17)	0.081 (2)	0.0161 (14)	0.0276 (14)	0.0127 (15)
C6	0.0327 (13)	0.0795 (19)	0.106 (2)	0.0041 (14)	0.0221 (15)	0.0161 (18)
C7	0.0344 (13)	0.0645 (16)	0.092 (2)	−0.0042 (12)	0.0073 (13)	0.0084 (15)
C8	0.0360 (12)	0.0474 (13)	0.0645 (16)	0.0012 (10)	0.0095 (11)	0.0067 (12)
C9	0.0339 (11)	0.0350 (11)	0.0482 (13)	0.0049 (9)	0.0094 (9)	0.0136 (9)
C10	0.0315 (11)	0.0326 (10)	0.0367 (11)	0.0026 (8)	0.0080 (8)	0.0072 (8)
C11	0.0324 (11)	0.0352 (11)	0.0375 (11)	−0.0038 (9)	0.0045 (8)	0.0014 (9)
C12	0.0375 (12)	0.0467 (13)	0.0483 (13)	−0.0069 (10)	0.0130 (9)	−0.0136 (10)
C13	0.0360 (11)	0.0367 (11)	0.0354 (11)	−0.0006 (9)	0.0089 (9)	0.0009 (9)
C14	0.0480 (15)	0.083 (2)	0.0647 (17)	−0.0268 (14)	0.0184 (13)	−0.0101 (15)
C15	0.0530 (17)	0.098 (2)	0.093 (2)	−0.0358 (16)	0.0169 (16)	−0.0089 (19)
C16	0.0423 (16)	0.0655 (19)	0.114 (3)	−0.0164 (14)	−0.0072 (16)	−0.0147 (18)
C17	0.0533 (17)	0.084 (2)	0.087 (2)	−0.0036 (15)	−0.0049 (15)	−0.0427 (18)
C18	0.0399 (14)	0.0733 (17)	0.0659 (17)	−0.0066 (12)	0.0079 (12)	−0.0227 (14)
N1	0.0324 (9)	0.0383 (9)	0.0365 (9)	−0.0034 (7)	0.0102 (7)	−0.0055 (7)
N2	0.0355 (10)	0.0449 (10)	0.0458 (11)	−0.0082 (8)	0.0059 (8)	−0.0046 (8)
O1	0.0363 (8)	0.0436 (8)	0.0452 (8)	−0.0046 (6)	0.0106 (6)	−0.0091 (7)
O2	0.0334 (8)	0.0491 (9)	0.0390 (8)	−0.0071 (7)	0.0107 (6)	−0.0067 (7)
O3	0.0468 (9)	0.0618 (10)	0.0512 (9)	−0.0097 (8)	0.0233 (7)	−0.0191 (8)

Geometric parameters (Å, º) top

Cu1—O1	1.9139 (14)	C9—C10	1.459 (3)
Cu1—N1	1.9296 (17)	C10—C11	1.422 (3)
Cu1—O2	1.9702 (14)	C11—N1	1.290 (3)
Cu1—N2	2.0136 (17)	C11—H11	0.9300
Cu1—O3ⁱ	2.3520 (16)	C12—N1	1.457 (3)
C1—O1	1.298 (2)	C12—C13	1.518 (3)
C1—C10	1.410 (3)	C12—H12A	0.9700
C1—C2	1.428 (3)	C12—H12B	0.9700
C2—C3	1.352 (3)	C13—O3	1.229 (2)
C2—H2	0.9300	C13—O2	1.268 (2)
C3—C4	1.411 (4)	C14—N2	1.336 (3)
C3—H3	0.9300	C14—C15	1.365 (4)
C4—C9	1.412 (3)	C14—H14	0.9300
C4—C5	1.413 (3)	C15—C16	1.354 (5)
C5—C6	1.350 (4)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.373 (4)
C6—C7	1.397 (4)	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.383 (4)
C7—C8	1.373 (3)	C17—H17	0.9300
C7—H7	0.9300	C18—N2	1.324 (3)
C8—C9	1.411 (3)	C18—H18	0.9300
C8—H8	0.9300	O3—Cu1ⁱⁱ	2.3520 (16)

O1—Cu1—N1	90.96 (7)	C1—C10—C9	119.63 (19)
O1—Cu1—O2	167.63 (6)	C11—C10—C9	119.40 (19)
N1—Cu1—O2	83.77 (6)	N1—C11—C10	125.71 (19)
O1—Cu1—N2	91.38 (7)	N1—C11—H11	117.1
N1—Cu1—N2	172.14 (7)	C10—C11—H11	117.1
O2—Cu1—N2	92.44 (7)	N1—C12—C13	110.20 (17)
O1—Cu1—O3ⁱ	100.09 (6)	N1—C12—H12A	109.6
N1—Cu1—O3ⁱ	97.45 (7)	C13—C12—H12A	109.6
O2—Cu1—O3ⁱ	91.71 (6)	N1—C12—H12B	109.6
N2—Cu1—O3ⁱ	89.52 (7)	C13—C12—H12B	109.6
O1—C1—C10	125.43 (19)	H12A—C12—H12B	108.1
O1—C1—C2	116.02 (19)	O3—C13—O2	124.69 (19)
C10—C1—C2	118.5 (2)	O3—C13—C12	118.91 (19)
C3—C2—C1	121.4 (2)	O2—C13—C12	116.38 (17)
C3—C2—H2	119.3	N2—C14—C15	123.1 (3)
C1—C2—H2	119.3	N2—C14—H14	118.5
C2—C3—C4	122.1 (2)	C15—C14—H14	118.5
C2—C3—H3	118.9	C16—C15—C14	119.4 (3)
C4—C3—H3	118.9	C16—C15—H15	120.3
C3—C4—C9	118.9 (2)	C14—C15—H15	120.3
C3—C4—C5	121.2 (2)	C15—C16—C17	118.8 (3)
C9—C4—C5	119.9 (2)	C15—C16—H16	120.6
C6—C5—C4	121.5 (3)	C17—C16—H16	120.6
C6—C5—H5	119.3	C16—C17—C18	118.7 (3)
C4—C5—H5	119.3	C16—C17—H17	120.6
C5—C6—C7	119.3 (2)	C18—C17—H17	120.6
C5—C6—H6	120.4	N2—C18—C17	122.7 (3)
C7—C6—H6	120.4	N2—C18—H18	118.7
C8—C7—C6	120.8 (3)	C17—C18—H18	118.7
C8—C7—H7	119.6	C11—N1—C12	119.25 (17)
C6—C7—H7	119.6	C11—N1—Cu1	128.09 (14)
C7—C8—C9	121.5 (2)	C12—N1—Cu1	112.60 (13)
C7—C8—H8	119.3	C18—N2—C14	117.3 (2)
C9—C8—H8	119.3	C18—N2—Cu1	121.30 (16)
C8—C9—C4	117.0 (2)	C14—N2—Cu1	121.35 (17)
C8—C9—C10	123.8 (2)	C1—O1—Cu1	128.69 (13)
C4—C9—C10	119.2 (2)	C13—O2—Cu1	115.74 (12)
C1—C10—C11	120.96 (18)	C13—O3—Cu1ⁱⁱ	132.41 (14)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₃H₉NO₃)(C₅H₅N)]
M_r	369.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.508 (4), 11.747 (3), 9.407 (3)
β (°)	101.805 (3)
V (Å³)	1569.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.41
Crystal size (mm)	0.30 × 0.30 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.662, 0.703
No. of measured, independent and observed [I > 2σ(I)] reflections	7938, 2770, 2460
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.069, 1.04
No. of reflections	2770
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O1	1.9139 (14)	Cu1—N2	2.0136 (17)
Cu1—N1	1.9296 (17)	Cu1—O3ⁱ	2.3520 (16)
Cu1—O2	1.9702 (14)

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

This research was supported by the National Sciences Foundation of China (No. 20877036) and the Top-class Foundation of Pingdingshan University (No. 2008010 and 2009001).

References

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