(2,2'-Bipyridine-κN,N')[N-(2-oxido-1-naphthyl-idene)threoninato-κO,N,O]copper(II).

In the title complex, [Cu(C(15)H(13)NO(4))(C(10)H(8)N(2))], the Schiff base ligand is derived from the condensation of 2-hydr-oxy-1-naphthaldehyde and l-threonine. The Cu(II) atom is five-coordinated by one N atom and two O atoms from the Schiff base ligand and by two N atoms from a 2,2'-bipyridine ligand in a distorted square-pyramidal geometry. In the crystal structure, the combination of inter-molecular O-H⋯O and C-H⋯O hydrogen bonds leads to a two-dimensional network.

Related literature

For related literature, see: Garnovski et al. (1993 ▶); Kalagouda et al. (2006 ▶); Wang et al. (1999 ▶).

Experimental

Crystal data

[Cu(C15H13NO4)(C10H8N2)]

M = 490.99

Orthorhombic,

a = 9.955 (2) Å

b = 12.180 (3) Å

c = 18.438 (4) Å

V = 2235.6 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.01 mm−1

T = 298 (2) K

0.29 × 0.28 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.757, T max = 0.855

14242 measured reflections

5278 independent reflections

4243 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.088

S = 1.04

5278 reflections

300 parameters

492 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.54 e Å−3

Absolute structure: Flack (1983 ▶), 2229 Friedel pairs

Flack parameter: −0.005 (13)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536808012191/hy2129sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012191/hy2129Isup2.hkl

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

[Cu(C15H13NO4)(C10H8N2)]	F000 = 1012
Mr = 490.99	Dx = 1.459 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5604 reflections
a = 9.955 (2) Å	θ = 2.3–26.1º
b = 12.180 (3) Å	µ = 1.01 mm−1
c = 18.438 (4) Å	T = 298 (2) K
V = 2235.6 (9) Å3	Block, blue
Z = 4	0.29 × 0.28 × 0.16 mm

Bruker SMART APEX CCD area-detector diffractometer	5278 independent reflections
Radiation source: fine-focus sealed tube	4243 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
T = 298(2) K	θmax = 28.3º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.757, Tmax = 0.855	k = −14→16
14242 measured reflections	l = −20→24

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0472P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.089	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.32 e Å−3
5278 reflections	Δρmin = −0.54 e Å−3
300 parameters	Extinction correction: none
492 restraints	Absolute structure: Flack (1983), 2229 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.005 (13)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
Cu1	0.32501 (3)	1.00767 (2)	0.977106 (17)	0.03806 (10)
N1	0.1622 (2)	1.08781 (15)	0.95744 (11)	0.0313 (4)
N2	0.2672 (3)	0.89079 (19)	1.06492 (15)	0.0491 (6)
N3	0.5005 (2)	0.93672 (19)	1.00252 (14)	0.0480 (6)
O4	0.3191 (2)	0.93362 (17)	0.88490 (11)	0.0498 (5)
O2	0.29386 (19)	1.31490 (16)	1.05070 (12)	0.0512 (5)
O1	0.37076 (18)	1.14608 (15)	1.03256 (11)	0.0424 (4)
O3	−0.05190 (19)	1.07490 (16)	1.05400 (12)	0.0474 (5)
H3	−0.0961	1.1082	1.0236	0.071*
C1	0.2783 (3)	1.2178 (2)	1.03223 (14)	0.0371 (6)
C2	0.1394 (3)	1.17825 (19)	1.00763 (13)	0.0319 (5)
H28	0.0912	1.2379	0.9832	0.038*
C3	0.0596 (3)	1.1395 (2)	1.07501 (15)	0.0368 (6)
H29	0.1194	1.0925	1.1037	0.044*
C4	0.0177 (3)	1.2351 (3)	1.12313 (16)	0.0510 (7)
H21A	−0.0285	1.2076	1.1651	0.077*
H21B	−0.0409	1.2830	1.0965	0.077*
H21C	0.0960	1.2750	1.1382	0.077*
C5	0.0856 (2)	1.0765 (2)	0.90139 (14)	0.0325 (5)
H11	0.0125	1.1237	0.8978	0.039*
C6	0.1028 (2)	0.9982 (2)	0.84450 (12)	0.0363 (5)
C7	0.2228 (3)	0.9366 (2)	0.83774 (15)	0.0415 (6)
C8	0.2402 (3)	0.8722 (3)	0.77391 (16)	0.0545 (8)
H18	0.3199	0.8335	0.7678	0.065*
C9	0.1453 (4)	0.8654 (3)	0.72205 (16)	0.0560 (8)
H19	0.1615	0.8224	0.6813	0.067*
C10	0.0215 (3)	0.9221 (2)	0.72803 (15)	0.0452 (6)
C11	−0.0016 (3)	0.9893 (2)	0.78988 (13)	0.0397 (6)
C12	−0.1269 (3)	1.0408 (2)	0.79527 (17)	0.0495 (7)
H27	−0.1453	1.0845	0.8354	0.059*
C13	−0.2234 (4)	1.0284 (3)	0.74247 (19)	0.0588 (8)
H26	−0.3055	1.0640	0.7475	0.071*
C14	−0.2000 (4)	0.9635 (3)	0.68174 (18)	0.0621 (9)
H25	−0.2659	0.9556	0.6464	0.074*
C15	−0.0795 (4)	0.9115 (3)	0.67446 (17)	0.0572 (8)
H15	−0.0634	0.8685	0.6337	0.069*
C16	0.1466 (4)	0.8711 (3)	1.0941 (2)	0.0660 (9)
H17	0.0701	0.8976	1.0710	0.079*
C17	0.1333 (6)	0.8119 (3)	1.1577 (3)	0.0965 (13)
H22	0.0488	0.7999	1.1777	0.116*
C18	0.2463 (6)	0.7710 (4)	1.1912 (3)	0.1063 (14)
H36	0.2387	0.7302	1.2336	0.128*
C19	0.3693 (5)	0.7909 (3)	1.1617 (3)	0.0883 (12)
H37	0.4468	0.7665	1.1849	0.106*
C20	0.3776 (4)	0.8483 (2)	1.09632 (19)	0.0579 (8)
C21	0.5052 (3)	0.8664 (2)	1.05811 (19)	0.0524 (7)
C22	0.6242 (4)	0.8126 (3)	1.0751 (2)	0.0701 (10)
H33	0.6271	0.7624	1.1131	0.084*
C23	0.7371 (4)	0.8343 (3)	1.0354 (3)	0.0775 (11)
H23	0.8169	0.7986	1.0468	0.093*
C24	0.7348 (3)	0.9067 (3)	0.9799 (3)	0.0719 (10)
H24	0.8118	0.9222	0.9532	0.086*
C25	0.6136 (3)	0.9570 (3)	0.9642 (2)	0.0634 (9)
H32	0.6097	1.0066	0.9259	0.076*

	U11	U22	U33	U12	U13	U23
Cu1	0.03383 (16)	0.04027 (16)	0.04008 (17)	0.00393 (14)	−0.00421 (14)	0.00230 (15)
N1	0.0301 (10)	0.0347 (10)	0.0291 (11)	0.0002 (9)	0.0011 (9)	−0.0009 (8)
N2	0.0536 (15)	0.0405 (13)	0.0531 (16)	−0.0017 (11)	−0.0030 (13)	0.0083 (12)
N3	0.0409 (13)	0.0384 (13)	0.0647 (17)	0.0035 (10)	−0.0093 (12)	0.0003 (11)
O4	0.0456 (11)	0.0590 (12)	0.0448 (12)	0.0165 (10)	−0.0016 (11)	−0.0084 (9)
O2	0.0434 (11)	0.0466 (11)	0.0636 (14)	−0.0096 (9)	0.0033 (10)	−0.0158 (10)
O1	0.0341 (9)	0.0460 (10)	0.0470 (12)	−0.0025 (8)	−0.0092 (9)	−0.0015 (9)
O3	0.0356 (10)	0.0553 (12)	0.0514 (13)	−0.0103 (9)	0.0020 (9)	0.0047 (10)
C1	0.0398 (13)	0.0424 (13)	0.0291 (13)	−0.0075 (11)	0.0053 (11)	−0.0008 (11)
C2	0.0348 (12)	0.0333 (12)	0.0275 (12)	0.0016 (10)	−0.0021 (10)	−0.0008 (9)
C3	0.0339 (13)	0.0442 (14)	0.0323 (13)	−0.0029 (11)	0.0013 (11)	0.0017 (11)
C4	0.0536 (18)	0.0621 (19)	0.0374 (15)	0.0016 (15)	0.0060 (14)	−0.0050 (14)
C5	0.0326 (12)	0.0360 (12)	0.0288 (12)	0.0016 (10)	−0.0001 (10)	0.0002 (10)
C6	0.0456 (13)	0.0364 (12)	0.0270 (11)	0.0003 (13)	0.0012 (10)	−0.0009 (11)
C7	0.0486 (15)	0.0413 (14)	0.0346 (14)	0.0009 (12)	0.0065 (12)	−0.0036 (11)
C8	0.0637 (19)	0.0570 (17)	0.0428 (17)	0.0105 (15)	0.0104 (15)	−0.0090 (14)
C9	0.074 (2)	0.0580 (16)	0.0354 (15)	−0.0053 (16)	0.0078 (15)	−0.0131 (13)
C10	0.0586 (16)	0.0469 (15)	0.0299 (13)	−0.0123 (13)	0.0007 (13)	−0.0025 (11)
C11	0.0510 (14)	0.0392 (13)	0.0291 (11)	−0.0082 (13)	−0.0017 (11)	0.0002 (11)
C12	0.0552 (16)	0.0542 (15)	0.0392 (15)	−0.0003 (13)	−0.0115 (13)	−0.0065 (12)
C13	0.0596 (17)	0.065 (2)	0.0515 (17)	−0.0031 (15)	−0.0187 (15)	−0.0011 (15)
C14	0.076 (2)	0.0662 (18)	0.0440 (16)	−0.0210 (16)	−0.0221 (16)	0.0030 (14)
C15	0.079 (2)	0.0582 (17)	0.0344 (15)	−0.0206 (16)	−0.0067 (15)	−0.0039 (13)
C16	0.074 (2)	0.0503 (17)	0.074 (2)	−0.0007 (16)	0.0131 (19)	0.0167 (16)
C17	0.104 (3)	0.085 (3)	0.101 (3)	0.002 (2)	0.034 (3)	0.038 (2)
C18	0.128 (3)	0.098 (3)	0.092 (3)	0.009 (3)	0.010 (3)	0.049 (2)
C19	0.100 (3)	0.080 (2)	0.084 (2)	0.015 (2)	−0.007 (2)	0.035 (2)
C20	0.0753 (19)	0.0387 (14)	0.0597 (18)	0.0037 (15)	−0.0113 (17)	0.0086 (14)
C21	0.0575 (17)	0.0352 (14)	0.0645 (18)	0.0071 (13)	−0.0215 (15)	−0.0033 (14)
C22	0.076 (2)	0.0502 (17)	0.084 (2)	0.0146 (17)	−0.029 (2)	−0.0012 (17)
C23	0.060 (2)	0.063 (2)	0.109 (3)	0.0182 (17)	−0.031 (2)	−0.020 (2)
C24	0.0489 (17)	0.0566 (18)	0.110 (3)	0.0058 (15)	−0.010 (2)	−0.015 (2)
C25	0.0492 (17)	0.0481 (16)	0.093 (2)	0.0030 (13)	−0.0050 (18)	−0.0026 (16)

Cu1—O4	1.925 (2)	C8—H18	0.9300
Cu1—N1	1.926 (2)	C9—C10	1.417 (5)
Cu1—N3	2.005 (2)	C9—H19	0.9300
Cu1—O1	2.0236 (18)	C10—C15	1.415 (4)
Cu1—N2	2.231 (3)	C10—C11	1.422 (4)
N1—C5	1.292 (3)	C11—C12	1.400 (4)
N1—C2	1.457 (3)	C12—C13	1.376 (4)
N2—C16	1.338 (4)	C12—H27	0.9300
N2—C20	1.345 (4)	C13—C14	1.390 (5)
N3—C21	1.337 (4)	C13—H26	0.9300
N3—C25	1.352 (4)	C14—C15	1.363 (5)
O4—C7	1.295 (4)	C14—H25	0.9300
O2—C1	1.240 (3)	C15—H15	0.9300
O1—C1	1.269 (3)	C16—C17	1.384 (5)
O3—C3	1.415 (3)	C16—H17	0.9300
O3—H3	0.8200	C17—C18	1.376 (7)
C1—C2	1.533 (4)	C17—H22	0.9300
C2—C3	1.548 (4)	C18—C19	1.362 (7)
C2—H28	0.9800	C18—H36	0.9300
C3—C4	1.522 (4)	C19—C20	1.397 (5)
C3—H29	0.9800	C19—H37	0.9300
C4—H21A	0.9600	C20—C21	1.469 (5)
C4—H21B	0.9600	C21—C22	1.390 (5)
C4—H21C	0.9600	C22—C23	1.366 (6)
C5—C6	1.428 (3)	C22—H33	0.9300
C5—H11	0.9300	C23—C24	1.352 (6)
C6—C7	1.417 (4)	C23—H23	0.9300
C6—C11	1.452 (3)	C24—C25	1.384 (5)
C7—C8	1.425 (4)	C24—H24	0.9300
C8—C9	1.346 (5)	C25—H32	0.9300
O4—Cu1—N1	92.62 (8)	C9—C8—H18	118.8
O4—Cu1—N3	91.77 (9)	C7—C8—H18	118.8
N1—Cu1—N3	174.65 (9)	C8—C9—C10	121.6 (3)
O4—Cu1—O1	147.49 (9)	C8—C9—H19	119.2
N1—Cu1—O1	82.08 (8)	C10—C9—H19	119.2
N3—Cu1—O1	92.57 (9)	C15—C10—C9	121.3 (3)
O4—Cu1—N2	109.51 (10)	C15—C10—C11	119.8 (3)
N1—Cu1—N2	104.07 (9)	C9—C10—C11	118.9 (3)
N3—Cu1—N2	77.29 (10)	C12—C11—C10	117.3 (3)
O1—Cu1—N2	102.88 (9)	C12—C11—C6	123.7 (2)
C5—N1—C2	119.8 (2)	C10—C11—C6	118.9 (3)
C5—N1—Cu1	126.40 (17)	C13—C12—C11	121.5 (3)
C2—N1—Cu1	113.27 (15)	C13—C12—H27	119.3
C16—N2—C20	119.4 (3)	C11—C12—H27	119.3
C16—N2—Cu1	129.6 (2)	C12—C13—C14	121.0 (3)
C20—N2—Cu1	110.3 (2)	C12—C13—H26	119.5
C21—N3—C25	119.3 (3)	C14—C13—H26	119.5
C21—N3—Cu1	119.1 (2)	C15—C14—C13	119.4 (3)
C25—N3—Cu1	121.6 (2)	C15—C14—H25	120.3
C7—O4—Cu1	127.02 (18)	C13—C14—H25	120.3
C1—O1—Cu1	114.08 (16)	C14—C15—C10	120.9 (3)
C3—O3—H3	109.5	C14—C15—H15	119.5
O2—C1—O1	124.4 (2)	C10—C15—H15	119.5
O2—C1—C2	119.6 (2)	N2—C16—C17	121.3 (4)
O1—C1—C2	116.1 (2)	N2—C16—H17	119.3
N1—C2—C1	106.54 (19)	C17—C16—H17	119.3
N1—C2—C3	111.06 (19)	C18—C17—C16	119.4 (5)
C1—C2—C3	108.7 (2)	C18—C17—H22	120.3
N1—C2—H28	110.1	C16—C17—H22	120.3
C1—C2—H28	110.1	C19—C18—C17	119.5 (4)
C3—C2—H28	110.1	C19—C18—H36	120.3
O3—C3—C4	111.7 (2)	C17—C18—H36	120.3
O3—C3—C2	110.6 (2)	C18—C19—C20	119.1 (4)
C4—C3—C2	112.0 (2)	C18—C19—H37	120.4
O3—C3—H29	107.4	C20—C19—H37	120.4
C4—C3—H29	107.4	N2—C20—C19	121.1 (4)
C2—C3—H29	107.4	N2—C20—C21	116.2 (3)
C3—C4—H21A	109.5	C19—C20—C21	122.7 (4)
C3—C4—H21B	109.5	N3—C21—C22	120.3 (4)
H21A—C4—H21B	109.5	N3—C21—C20	115.7 (3)
C3—C4—H21C	109.5	C22—C21—C20	123.9 (3)
H21A—C4—H21C	109.5	C23—C22—C21	119.3 (4)
H21B—C4—H21C	109.5	C23—C22—H33	120.4
N1—C5—C6	126.0 (2)	C21—C22—H33	120.4
N1—C5—H11	117.0	C24—C23—C22	121.2 (3)
C6—C5—H11	117.0	C24—C23—H23	119.4
C7—C6—C5	121.3 (2)	C22—C23—H23	119.4
C7—C6—C11	120.2 (2)	C23—C24—C25	117.5 (4)
C5—C6—C11	118.3 (2)	C23—C24—H24	121.3
O4—C7—C6	125.5 (2)	C25—C24—H24	121.3
O4—C7—C8	116.7 (3)	N3—C25—C24	122.4 (4)
C6—C7—C8	117.8 (3)	N3—C25—H32	118.8
C9—C8—C7	122.4 (3)	C24—C25—H32	118.8
C1—C2—C3—C4	71.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2i	0.82	1.99	2.808 (3)	178
C5—H11···O2i	0.93	2.49	3.311 (3)	147
C12—H27···O2i	0.93	2.50	3.431 (4)	174
C14—H25···O3ii	0.93	2.52	3.445 (4)	177

Cu1—O4	1.925 (2)
Cu1—N1	1.926 (2)
Cu1—N3	2.005 (2)
Cu1—O1	2.0236 (18)
Cu1—N2	2.231 (3)

O4—Cu1—N1	92.62 (8)
O4—Cu1—N3	91.77 (9)
N1—Cu1—N3	174.65 (9)
O4—Cu1—O1	147.49 (9)
N1—Cu1—O1	82.08 (8)
N3—Cu1—O1	92.57 (9)
O4—Cu1—N2	109.51 (10)
N1—Cu1—N2	104.07 (9)
N3—Cu1—N2	77.29 (10)
O1—Cu1—N2	102.88 (9)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2i	0.82	1.99	2.808 (3)	178
C5—H11⋯O2i	0.93	2.49	3.311 (3)	147
C12—H27⋯O2i	0.93	2.50	3.431 (4)	174
C14—H25⋯O3ii	0.93	2.52	3.445 (4)	177

Symmetry codes: (i) ; (ii) .