(2-Oxido-1-naphthaldehyde benzoyl-hydrazonato-κN,N',O)pyridine-copper(II).

In the mononuclear title compound, [Cu(II)(C(18)H(12)N(2)O(2))(C(5)H(5)N)], the Cu(II) ion is coordinated by two O atoms and one N atom from the dianionic tridentate L(2-) ligand (H(2)L is 2-hy-droxy-1-naphthaldehyde benzoyl-hydrazide) and one N atom from a pyridine mol-ecule in a CuN(2)O(2) distorted square-planar coordination environment.

Related literature

For the preparation of the Schiff base, see: Qiao et al. (2010 ▶). For chemically related applications arising from Schiff base compounds, see: Ando et al. (2004 ▶); Anford et al. (1998 ▶); Guo et al. (2010 ▶). For related structures, see: Ali et al. (2004 ▶); Sun et al. (2011 ▶); Xu et al. (2006 ▶); Yu et al. (2010 ▶).

Experimental

Crystal data

[Cu(C18H12N2O2)(C5H5N)]

M = 430.94

Monoclinic,

a = 11.6196 (6) Å

b = 8.4254 (4) Å

c = 19.6194 (10) Å

β = 106.247 (1)°

V = 1844.03 (16) Å3

Z = 4

Mo Kα radiation

μ = 1.21 mm−1

T = 185 K

0.14 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.849, T max = 0.889

8559 measured reflections

3619 independent reflections

2860 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.086

S = 1.03

3619 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011081/zq2095sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011081/zq2095Isup2.hkl

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

[Cu(C18H12N2O2)(C5H5N)]	F(000) = 884
Mr = 430.94	Dx = 1.552 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9033 reflections
a = 11.6196 (6) Å	θ = 4.8–51.9°
b = 8.4254 (4) Å	µ = 1.21 mm−1
c = 19.6194 (10) Å	T = 185 K
β = 106.247 (1)°	Block, brown
V = 1844.03 (16) Å3	0.14 × 0.12 × 0.10 mm
Z = 4

Bruker APEXII CCD area detector diffractometer	3619 independent reflections
Radiation source: fine-focus sealed tube	2860 reflections with I > 2σ(I)
graphite	Rint = 0.031
phi and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
Tmin = 0.849, Tmax = 0.889	k = −6→10
8559 measured reflections	l = −18→24

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0353P)2 + 1.0945P] where P = (Fo2 + 2Fc2)/3
3619 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.86976 (3)	0.13588 (4)	0.539632 (16)	0.02191 (11)
N1	0.89789 (18)	0.1188 (2)	0.44895 (11)	0.0200 (5)
N2	0.99966 (18)	0.1976 (3)	0.44156 (11)	0.0216 (5)
N3	0.86766 (19)	0.1483 (2)	0.64115 (11)	0.0226 (5)
O1	0.72604 (15)	0.0186 (2)	0.51138 (9)	0.0247 (4)
O2	1.00963 (15)	0.2688 (2)	0.55668 (9)	0.0238 (4)
C1	0.7084 (2)	−0.1291 (3)	0.26471 (14)	0.0265 (6)
H1	0.7807	−0.0755	0.2655	0.032*
C2	0.6465 (3)	−0.2069 (3)	0.20399 (14)	0.0300 (6)
H2	0.6762	−0.2046	0.1635	0.036*
C3	0.5411 (3)	−0.2891 (3)	0.20059 (15)	0.0306 (6)
H3	0.4997	−0.3440	0.1586	0.037*
C4	0.4982 (3)	−0.2894 (3)	0.25876 (15)	0.0313 (7)
H4	0.4259	−0.3444	0.2567	0.038*
C5	0.5588 (2)	−0.2100 (3)	0.32154 (14)	0.0261 (6)
C6	0.5135 (2)	−0.2110 (3)	0.38178 (15)	0.0295 (6)
H6	0.4416	−0.2672	0.3794	0.035*
C7	0.5702 (2)	−0.1339 (3)	0.44258 (14)	0.0267 (6)
H7	0.5366	−0.1366	0.4815	0.032*
C8	0.6791 (2)	−0.0489 (3)	0.44957 (13)	0.0221 (6)
C9	0.7276 (2)	−0.0447 (3)	0.39116 (13)	0.0205 (5)
C10	0.6671 (2)	−0.1266 (3)	0.32608 (13)	0.0225 (6)
C11	0.8363 (2)	0.0379 (3)	0.39455 (13)	0.0216 (6)
H11	0.8658	0.0333	0.3541	0.026*
C12	1.0481 (2)	0.2750 (3)	0.50057 (13)	0.0213 (6)
C13	1.1522 (2)	0.3790 (3)	0.50397 (14)	0.0219 (6)
C14	1.1922 (3)	0.4090 (3)	0.44463 (15)	0.0329 (7)
H14	1.1537	0.3597	0.4006	0.039*
C15	1.2877 (3)	0.5103 (4)	0.44947 (16)	0.0385 (7)
H15	1.3142	0.5301	0.4086	0.046*
C16	1.3449 (3)	0.5828 (3)	0.51292 (17)	0.0361 (7)
H16	1.4105	0.6522	0.5158	0.043*
C17	1.3063 (2)	0.5537 (3)	0.57197 (16)	0.0328 (7)
H17	1.3455	0.6032	0.6158	0.039*
C18	1.2107 (2)	0.4527 (3)	0.56769 (14)	0.0262 (6)
H18	1.1847	0.4334	0.6087	0.031*
C19	0.9510 (2)	0.2352 (3)	0.68806 (15)	0.0323 (7)
H19	1.0071	0.2946	0.6714	0.039*
C20	0.9577 (3)	0.2408 (4)	0.75936 (15)	0.0350 (7)
H20	1.0176	0.3027	0.7911	0.042*
C21	0.8762 (3)	0.1554 (3)	0.78380 (14)	0.0313 (7)
H21	0.8795	0.1564	0.8327	0.038*
C22	0.7900 (3)	0.0686 (4)	0.73614 (15)	0.0332 (7)
H22	0.7319	0.0101	0.7515	0.040*
C23	0.7889 (2)	0.0676 (3)	0.66537 (14)	0.0275 (6)
H23	0.7294	0.0067	0.6328	0.033*

	U11	U22	U33	U12	U13	U23
Cu1	0.02087 (18)	0.02664 (19)	0.01893 (17)	−0.00342 (14)	0.00672 (13)	−0.00051 (14)
N1	0.0180 (11)	0.0199 (11)	0.0215 (11)	−0.0023 (9)	0.0045 (9)	0.0025 (9)
N2	0.0180 (11)	0.0242 (11)	0.0227 (11)	−0.0027 (9)	0.0062 (9)	0.0032 (9)
N3	0.0222 (11)	0.0258 (12)	0.0204 (11)	−0.0017 (10)	0.0069 (9)	−0.0012 (9)
O1	0.0248 (10)	0.0274 (10)	0.0233 (10)	−0.0047 (8)	0.0092 (8)	−0.0023 (8)
O2	0.0240 (10)	0.0289 (10)	0.0201 (9)	−0.0047 (8)	0.0085 (8)	−0.0025 (8)
C1	0.0250 (14)	0.0242 (14)	0.0281 (14)	0.0001 (12)	0.0037 (12)	0.0004 (12)
C2	0.0352 (16)	0.0268 (15)	0.0262 (15)	0.0026 (13)	0.0053 (13)	−0.0006 (12)
C3	0.0333 (16)	0.0248 (15)	0.0277 (15)	0.0017 (13)	−0.0016 (13)	−0.0075 (12)
C4	0.0269 (15)	0.0256 (15)	0.0353 (16)	−0.0040 (12)	−0.0011 (13)	−0.0040 (13)
C5	0.0266 (15)	0.0196 (14)	0.0296 (15)	−0.0009 (11)	0.0038 (12)	0.0018 (12)
C6	0.0249 (15)	0.0262 (15)	0.0367 (17)	−0.0071 (12)	0.0073 (13)	0.0012 (13)
C7	0.0243 (14)	0.0267 (15)	0.0298 (15)	−0.0027 (12)	0.0086 (12)	0.0036 (12)
C8	0.0223 (13)	0.0189 (13)	0.0235 (14)	0.0012 (11)	0.0039 (11)	0.0027 (11)
C9	0.0202 (13)	0.0175 (13)	0.0217 (13)	0.0002 (10)	0.0025 (11)	0.0018 (10)
C10	0.0219 (13)	0.0178 (13)	0.0249 (14)	0.0031 (11)	0.0018 (11)	0.0029 (11)
C11	0.0248 (14)	0.0208 (13)	0.0201 (13)	0.0033 (11)	0.0076 (11)	0.0037 (11)
C12	0.0221 (14)	0.0214 (14)	0.0208 (13)	0.0040 (11)	0.0067 (11)	0.0038 (11)
C13	0.0199 (13)	0.0195 (13)	0.0261 (14)	0.0014 (11)	0.0061 (11)	0.0034 (11)
C14	0.0372 (17)	0.0342 (16)	0.0293 (16)	−0.0103 (13)	0.0127 (13)	−0.0024 (13)
C15	0.0434 (19)	0.0386 (18)	0.0400 (18)	−0.0107 (15)	0.0222 (15)	0.0020 (14)
C16	0.0311 (16)	0.0264 (15)	0.054 (2)	−0.0115 (13)	0.0172 (15)	−0.0010 (14)
C17	0.0294 (16)	0.0286 (16)	0.0384 (17)	−0.0077 (13)	0.0063 (13)	−0.0087 (13)
C18	0.0271 (15)	0.0243 (14)	0.0284 (15)	−0.0013 (12)	0.0096 (12)	−0.0040 (12)
C19	0.0306 (16)	0.0393 (17)	0.0291 (15)	−0.0132 (14)	0.0119 (13)	−0.0048 (13)
C20	0.0385 (17)	0.0398 (18)	0.0264 (15)	−0.0112 (14)	0.0087 (13)	−0.0066 (13)
C21	0.0429 (17)	0.0316 (16)	0.0214 (14)	−0.0048 (13)	0.0120 (13)	−0.0026 (12)
C22	0.0374 (17)	0.0374 (17)	0.0287 (15)	−0.0117 (14)	0.0156 (13)	−0.0043 (13)
C23	0.0268 (15)	0.0327 (15)	0.0235 (14)	−0.0072 (12)	0.0075 (12)	−0.0031 (12)

Cu1—O1	1.8853 (17)	C8—C9	1.412 (3)
Cu1—N1	1.902 (2)	C9—C11	1.428 (3)
Cu1—O2	1.9243 (17)	C9—C10	1.449 (3)
Cu1—N3	2.001 (2)	C11—H11	0.9500
N1—C11	1.300 (3)	C12—C13	1.480 (3)
N1—N2	1.398 (3)	C13—C18	1.391 (4)
N2—C12	1.311 (3)	C13—C14	1.392 (4)
N3—C23	1.331 (3)	C14—C15	1.381 (4)
N3—C19	1.349 (3)	C14—H14	0.9500
O1—C8	1.312 (3)	C15—C16	1.379 (4)
O2—C12	1.300 (3)	C15—H15	0.9500
C1—C2	1.374 (4)	C16—C17	1.376 (4)
C1—C10	1.415 (4)	C16—H16	0.9500
C1—H1	0.9500	C17—C18	1.384 (4)
C2—C3	1.392 (4)	C17—H17	0.9500
C2—H2	0.9500	C18—H18	0.9500
C3—C4	1.367 (4)	C19—C20	1.380 (4)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.405 (4)	C20—C21	1.378 (4)
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.422 (4)	C21—C22	1.374 (4)
C5—C10	1.423 (4)	C21—H21	0.9500
C6—C7	1.356 (4)	C22—C23	1.385 (4)
C6—H6	0.9500	C22—H22	0.9500
C7—C8	1.427 (4)	C23—H23	0.9500
C7—H7	0.9500
O1—Cu1—N1	93.17 (8)	C1—C10—C5	116.4 (2)
O1—Cu1—O2	172.59 (7)	C1—C10—C9	124.1 (2)
N1—Cu1—O2	81.30 (8)	C5—C10—C9	119.6 (2)
O1—Cu1—N3	93.65 (8)	N1—C11—C9	124.8 (2)
N1—Cu1—N3	171.07 (8)	N1—C11—H11	117.6
O2—Cu1—N3	92.37 (8)	C9—C11—H11	117.6
C11—N1—N2	116.8 (2)	O2—C12—N2	124.3 (2)
C11—N1—Cu1	127.48 (17)	O2—C12—C13	117.2 (2)
N2—N1—Cu1	115.64 (15)	N2—C12—C13	118.6 (2)
C12—N2—N1	108.15 (19)	C18—C13—C14	118.5 (2)
C23—N3—C19	117.9 (2)	C18—C13—C12	119.5 (2)
C23—N3—Cu1	121.99 (18)	C14—C13—C12	122.0 (2)
C19—N3—Cu1	120.08 (17)	C15—C14—C13	120.3 (3)
C8—O1—Cu1	127.16 (16)	C15—C14—H14	119.9
C12—O2—Cu1	110.51 (16)	C13—C14—H14	119.9
C2—C1—C10	121.7 (3)	C16—C15—C14	120.7 (3)
C2—C1—H1	119.2	C16—C15—H15	119.6
C10—C1—H1	119.2	C14—C15—H15	119.6
C1—C2—C3	121.3 (3)	C17—C16—C15	119.5 (3)
C1—C2—H2	119.4	C17—C16—H16	120.2
C3—C2—H2	119.4	C15—C16—H16	120.2
C4—C3—C2	118.8 (3)	C16—C17—C18	120.2 (3)
C4—C3—H3	120.6	C16—C17—H17	119.9
C2—C3—H3	120.6	C18—C17—H17	119.9
C3—C4—C5	121.4 (3)	C17—C18—C13	120.7 (3)
C3—C4—H4	119.3	C17—C18—H18	119.6
C5—C4—H4	119.3	C13—C18—H18	119.6
C4—C5—C6	121.0 (3)	N3—C19—C20	122.5 (3)
C4—C5—C10	120.5 (3)	N3—C19—H19	118.8
C6—C5—C10	118.5 (2)	C20—C19—H19	118.8
C7—C6—C5	121.8 (2)	C21—C20—C19	119.0 (3)
C7—C6—H6	119.1	C21—C20—H20	120.5
C5—C6—H6	119.1	C19—C20—H20	120.5
C6—C7—C8	121.7 (2)	C22—C21—C20	118.8 (3)
C6—C7—H7	119.2	C22—C21—H21	120.6
C8—C7—H7	119.2	C20—C21—H21	120.6
O1—C8—C9	125.6 (2)	C21—C22—C23	119.1 (3)
O1—C8—C7	115.8 (2)	C21—C22—H22	120.4
C9—C8—C7	118.6 (2)	C23—C22—H22	120.4
C8—C9—C11	121.6 (2)	N3—C23—C22	122.7 (3)
C8—C9—C10	119.9 (2)	N3—C23—H23	118.6
C11—C9—C10	118.6 (2)	C22—C23—H23	118.6

Cu1—O1	1.8853 (17)
Cu1—N1	1.902 (2)
Cu1—O2	1.9243 (17)
Cu1—N3	2.001 (2)

O1—Cu1—N1	93.17 (8)
O1—Cu1—O2	172.59 (7)
N1—Cu1—O2	81.30 (8)
O1—Cu1—N3	93.65 (8)
N1—Cu1—N3	171.07 (8)
O2—Cu1—N3	92.37 (8)