catena-Poly[[pyridinecopper(II)]-μ-N-[(2-oxido-1-naphth-yl)methyl-ene]glycinato].

In the title compound, [Cu(C(13)H(9)NO(3))(C(5)H(5)N)], 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 carboxyl-ate 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(n class="CellLine">C13H9NO3)(C5H5N)]

M = 369.85

Monoclinic,

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 (; 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[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.069

S = 1.04

2770 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAIn class="Chemical">NT (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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037520/is2450sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037520/is2450Isup2.hkl

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

[Cu(C13H9NO3)(C5H5N)]	F(000) = 756
Mr = 369.85	Dx = 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

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

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(Fo2) + (0.0336P)2 + 0.6894P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2770 reflections	Δρmax = 0.26 e Å−3
218 parameters	Δρmin = −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)

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	0.754799 (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)

	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)

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)

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) .