Bis[1-(2-naphthyl-imino-meth-yl)-2-naphtholato-κN,O]copper(II).

In the title complex, [Cu(C(21)H(14)NO)(2)], the Cu(II) atom, lying on an inversion center, is coordinated by two bidentate 1-(2-naphthyl-imino-meth-yl)-2-naphtholate ligands in a trans arrangement, forming a slightly distorted square-planar coordination geometry. The mean planes of two naphthyl systems of the ligand make a dihedral angle of 40.32 (11)°.

Related literature

For general background to Schiff base complexes, see: Gamovski et al. (1993 ▶); Tarafder et al. (2002 ▶); Yang et al. (2000 ▶). For related structures, see: Unver et al. (2003 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

[Cu(C21H14NO)2]

M = 656.20

Monoclinic,

a = 5.648 (3) Å

b = 18.578 (8) Å

c = 14.796 (6) Å

β = 93.635 (5)°

V = 1549.4 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.75 mm−1

T = 298 K

0.35 × 0.10 × 0.04 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.780, T max = 0.971

7695 measured reflections

2721 independent reflections

1869 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.121

S = 1.10

2721 reflections

214 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.75 e Å−3

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/S1600536809030694/hy2212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030694/hy2212Isup2.hkl

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

[Cu(C21H14NO)2]	F(000) = 678
Mr = 656.20	Dx = 1.407 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2286 reflections
a = 5.648 (3) Å	θ = 2.2–25.2°
b = 18.578 (8) Å	µ = 0.75 mm−1
c = 14.796 (6) Å	T = 298 K
β = 93.635 (5)°	Needle, green
V = 1549.4 (12) Å3	0.35 × 0.10 × 0.04 mm
Z = 2

Bruker SMART 1000 CCD diffractometer	2721 independent reflections
Radiation source: fine-focus sealed tube	1869 reflections with I > 2σ(I)
graphite	Rint = 0.062
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.780, Tmax = 0.971	k = −22→21
7695 measured reflections	l = −15→17

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.P)2 + 3.3732P] where P = (Fo2 + 2Fc2)/3
2721 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.75 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.5000	0.5000	0.0330 (2)
N1	0.4680 (6)	0.58180 (17)	0.5874 (2)	0.0309 (9)
O1	0.2210 (5)	0.45773 (16)	0.5372 (2)	0.0411 (8)
C1	0.3354 (8)	0.5772 (2)	0.6562 (3)	0.0341 (11)
H1	0.3487	0.6148	0.6977	0.041*
C2	0.1725 (7)	0.5215 (2)	0.6753 (3)	0.0297 (10)
C3	0.1107 (8)	0.4686 (2)	0.6098 (3)	0.0340 (10)
C4	−0.0904 (8)	0.4233 (2)	0.6237 (3)	0.0364 (11)
H4	−0.1336	0.3884	0.5807	0.044*
C5	−0.2175 (8)	0.4301 (2)	0.6970 (3)	0.0410 (12)
H5	−0.3507	0.4013	0.7022	0.049*
C6	−0.1527 (8)	0.4806 (2)	0.7671 (3)	0.0372 (11)
C7	0.0473 (8)	0.5251 (2)	0.7577 (3)	0.0327 (10)
C8	0.1156 (9)	0.5708 (3)	0.8321 (3)	0.0448 (12)
H8	0.2512	0.5990	0.8298	0.054*
C9	−0.0143 (10)	0.5740 (3)	0.9069 (3)	0.0552 (14)
H9	0.0324	0.6050	0.9541	0.066*
C10	−0.2161 (10)	0.5315 (3)	0.9131 (4)	0.0588 (15)
H10	−0.3052	0.5348	0.9637	0.071*
C11	−0.2825 (9)	0.4848 (3)	0.8445 (3)	0.0500 (13)
H11	−0.4149	0.4556	0.8494	0.060*
C12	0.7489 (8)	0.6684 (2)	0.6569 (3)	0.0355 (11)
H12	0.7366	0.6458	0.7125	0.043*
C13	0.6125 (7)	0.6447 (2)	0.5833 (3)	0.0295 (10)
C14	0.6260 (9)	0.6813 (2)	0.4998 (3)	0.0398 (11)
H14	0.5292	0.6669	0.4499	0.048*
C15	0.7776 (9)	0.7369 (2)	0.4917 (3)	0.0432 (12)
H15	0.7829	0.7602	0.4362	0.052*
C16	0.9284 (8)	0.7605 (2)	0.5658 (3)	0.0418 (12)
C17	0.9088 (8)	0.7268 (2)	0.6506 (3)	0.0362 (11)
C18	1.0563 (9)	0.7503 (3)	0.7259 (3)	0.0492 (13)
H18	1.0404	0.7300	0.7827	0.059*
C19	1.2210 (10)	0.8026 (3)	0.7154 (4)	0.0671 (17)
H19	1.3191	0.8169	0.7650	0.081*
C20	1.2455 (10)	0.8353 (3)	0.6308 (5)	0.0677 (17)
H20	1.3591	0.8709	0.6244	0.081*
C21	1.1009 (10)	0.8144 (3)	0.5583 (4)	0.0580 (15)
H21	1.1167	0.8363	0.5025	0.070*

	U11	U22	U33	U12	U13	U23
Cu1	0.0312 (4)	0.0303 (4)	0.0371 (4)	−0.0027 (4)	−0.0018 (3)	−0.0056 (4)
N1	0.031 (2)	0.0240 (19)	0.037 (2)	−0.0042 (16)	−0.0053 (18)	−0.0032 (16)
O1	0.0391 (19)	0.0390 (18)	0.0447 (19)	−0.0039 (15)	−0.0004 (16)	−0.0144 (15)
C1	0.030 (3)	0.034 (2)	0.037 (3)	0.001 (2)	−0.005 (2)	−0.005 (2)
C2	0.024 (2)	0.029 (2)	0.035 (2)	0.0015 (18)	−0.0035 (19)	−0.0003 (18)
C3	0.030 (3)	0.031 (2)	0.040 (3)	0.000 (2)	−0.009 (2)	0.001 (2)
C4	0.025 (2)	0.035 (3)	0.049 (3)	−0.003 (2)	−0.005 (2)	0.002 (2)
C5	0.027 (3)	0.041 (3)	0.055 (3)	−0.006 (2)	−0.004 (2)	0.009 (2)
C6	0.035 (3)	0.038 (3)	0.039 (3)	0.008 (2)	−0.001 (2)	0.012 (2)
C7	0.030 (3)	0.032 (2)	0.035 (2)	0.0029 (19)	−0.004 (2)	0.0051 (19)
C8	0.043 (3)	0.054 (3)	0.037 (3)	−0.007 (2)	0.001 (2)	0.005 (2)
C9	0.071 (4)	0.058 (3)	0.036 (3)	0.002 (3)	0.004 (3)	−0.002 (2)
C10	0.062 (4)	0.068 (4)	0.049 (3)	0.005 (3)	0.020 (3)	0.009 (3)
C11	0.045 (3)	0.047 (3)	0.059 (3)	0.000 (2)	0.007 (3)	0.009 (3)
C12	0.043 (3)	0.036 (2)	0.027 (2)	0.003 (2)	−0.003 (2)	−0.002 (2)
C13	0.027 (2)	0.027 (2)	0.033 (3)	0.0024 (19)	−0.001 (2)	−0.0038 (19)
C14	0.047 (3)	0.038 (3)	0.034 (3)	−0.007 (2)	−0.006 (2)	−0.002 (2)
C15	0.054 (3)	0.042 (3)	0.033 (3)	−0.003 (2)	0.000 (2)	0.002 (2)
C16	0.040 (3)	0.034 (3)	0.052 (3)	−0.003 (2)	0.006 (2)	−0.005 (2)
C17	0.030 (3)	0.033 (3)	0.046 (3)	0.001 (2)	−0.003 (2)	−0.012 (2)
C18	0.053 (3)	0.042 (3)	0.050 (3)	−0.002 (3)	−0.016 (3)	−0.009 (2)
C19	0.057 (4)	0.061 (4)	0.081 (5)	−0.011 (3)	−0.013 (3)	−0.027 (3)
C20	0.050 (4)	0.058 (4)	0.094 (5)	−0.018 (3)	0.002 (3)	−0.016 (4)
C21	0.059 (4)	0.045 (3)	0.070 (4)	−0.014 (3)	0.008 (3)	−0.001 (3)

Cu1—O1	1.874 (3)	C9—H9	0.9300
Cu1—O1i	1.874 (3)	C10—C11	1.369 (7)
Cu1—N1i	2.011 (3)	C10—H10	0.9300
Cu1—N1	2.011 (3)	C11—H11	0.9300
N1—C1	1.304 (5)	C12—C13	1.367 (6)
N1—C13	1.428 (5)	C12—C17	1.417 (6)
O1—C3	1.292 (5)	C12—H12	0.9300
C1—C2	1.424 (6)	C13—C14	1.416 (6)
C1—H1	0.9300	C14—C15	1.352 (6)
C2—C3	1.409 (6)	C14—H14	0.9300
C2—C7	1.449 (6)	C15—C16	1.414 (6)
C3—C4	1.439 (6)	C15—H15	0.9300
C4—C5	1.344 (6)	C16—C21	1.406 (6)
C4—H4	0.9300	C16—C17	1.413 (6)
C5—C6	1.429 (6)	C17—C18	1.418 (6)
C5—H5	0.9300	C18—C19	1.361 (7)
C6—C11	1.401 (6)	C18—H18	0.9300
C6—C7	1.413 (6)	C19—C20	1.406 (8)
C7—C8	1.425 (6)	C19—H19	0.9300
C8—C9	1.367 (7)	C20—C21	1.363 (7)
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.395 (7)	C21—H21	0.9300
O1—Cu1—O1i	180.00 (16)	C11—C10—C9	119.7 (5)
O1—Cu1—N1i	89.07 (13)	C11—C10—H10	120.1
O1i—Cu1—N1i	90.93 (13)	C9—C10—H10	120.1
O1—Cu1—N1	90.93 (13)	C10—C11—C6	120.6 (5)
O1i—Cu1—N1	89.07 (13)	C10—C11—H11	119.7
N1i—Cu1—N1	180.00 (15)	C6—C11—H11	119.7
C1—N1—C13	116.4 (3)	C13—C12—C17	121.6 (4)
C1—N1—Cu1	122.1 (3)	C13—C12—H12	119.2
C13—N1—Cu1	121.0 (3)	C17—C12—H12	119.2
C3—O1—Cu1	129.6 (3)	C12—C13—C14	118.7 (4)
N1—C1—C2	127.8 (4)	C12—C13—N1	121.6 (4)
N1—C1—H1	116.1	C14—C13—N1	119.6 (4)
C2—C1—H1	116.1	C15—C14—C13	121.0 (4)
C3—C2—C1	120.4 (4)	C15—C14—H14	119.5
C3—C2—C7	119.8 (4)	C13—C14—H14	119.5
C1—C2—C7	119.3 (4)	C14—C15—C16	121.4 (4)
O1—C3—C2	124.7 (4)	C14—C15—H15	119.3
O1—C3—C4	117.0 (4)	C16—C15—H15	119.3
C2—C3—C4	118.3 (4)	C21—C16—C17	118.6 (5)
C5—C4—C3	121.8 (4)	C21—C16—C15	123.1 (5)
C5—C4—H4	119.1	C17—C16—C15	118.3 (4)
C3—C4—H4	119.1	C16—C17—C12	119.0 (4)
C4—C5—C6	121.5 (4)	C16—C17—C18	119.1 (4)
C4—C5—H5	119.3	C12—C17—C18	121.9 (4)
C6—C5—H5	119.3	C19—C18—C17	120.2 (5)
C11—C6—C7	120.7 (4)	C19—C18—H18	119.9
C11—C6—C5	120.5 (4)	C17—C18—H18	119.9
C7—C6—C5	118.8 (4)	C18—C19—C20	121.2 (5)
C6—C7—C8	116.8 (4)	C18—C19—H19	119.4
C6—C7—C2	119.5 (4)	C20—C19—H19	119.4
C8—C7—C2	123.7 (4)	C21—C20—C19	119.3 (5)
C9—C8—C7	121.3 (5)	C21—C20—H20	120.4
C9—C8—H8	119.4	C19—C20—H20	120.4
C7—C8—H8	119.4	C20—C21—C16	121.7 (5)
C8—C9—C10	120.8 (5)	C20—C21—H21	119.1
C8—C9—H9	119.6	C16—C21—H21	119.1
C10—C9—H9	119.6
O1—Cu1—N1—C1	19.0 (3)	C2—C7—C8—C9	177.5 (4)
O1i—Cu1—N1—C1	−161.0 (3)	C7—C8—C9—C10	1.2 (8)
O1—Cu1—N1—C13	−168.7 (3)	C8—C9—C10—C11	1.3 (8)
O1i—Cu1—N1—C13	11.3 (3)	C9—C10—C11—C6	−1.5 (8)
N1i—Cu1—O1—C3	161.7 (4)	C7—C6—C11—C10	−0.9 (7)
N1—Cu1—O1—C3	−18.3 (4)	C5—C6—C11—C10	177.9 (4)
C13—N1—C1—C2	178.5 (4)	C17—C12—C13—C14	−2.4 (6)
Cu1—N1—C1—C2	−8.8 (6)	C17—C12—C13—N1	174.0 (4)
N1—C1—C2—C3	−10.4 (7)	C1—N1—C13—C12	47.9 (6)
N1—C1—C2—C7	177.7 (4)	Cu1—N1—C13—C12	−124.9 (4)
Cu1—O1—C3—C2	5.6 (6)	C1—N1—C13—C14	−135.7 (4)
Cu1—O1—C3—C4	−174.8 (3)	Cu1—N1—C13—C14	51.6 (5)
C1—C2—C3—O1	13.0 (6)	C12—C13—C14—C15	2.7 (7)
C7—C2—C3—O1	−175.1 (4)	N1—C13—C14—C15	−173.8 (4)
C1—C2—C3—C4	−166.6 (4)	C13—C14—C15—C16	0.1 (7)
C7—C2—C3—C4	5.3 (6)	C14—C15—C16—C21	175.0 (5)
O1—C3—C4—C5	180.0 (4)	C14—C15—C16—C17	−3.1 (7)
C2—C3—C4—C5	−0.4 (6)	C21—C16—C17—C12	−174.9 (4)
C3—C4—C5—C6	−2.9 (7)	C15—C16—C17—C12	3.3 (7)
C4—C5—C6—C11	−177.5 (4)	C21—C16—C17—C18	2.6 (7)
C4—C5—C6—C7	1.2 (6)	C15—C16—C17—C18	−179.2 (4)
C11—C6—C7—C8	3.2 (6)	C13—C12—C17—C16	−0.6 (7)
C5—C6—C7—C8	−175.5 (4)	C13—C12—C17—C18	−178.0 (4)
C11—C6—C7—C2	−177.6 (4)	C16—C17—C18—C19	−2.8 (7)
C5—C6—C7—C2	3.7 (6)	C12—C17—C18—C19	174.6 (5)
C3—C2—C7—C6	−6.9 (6)	C17—C18—C19—C20	1.4 (8)
C1—C2—C7—C6	165.0 (4)	C18—C19—C20—C21	0.2 (9)
C3—C2—C7—C8	172.2 (4)	C19—C20—C21—C16	−0.4 (9)
C1—C2—C7—C8	−15.9 (6)	C17—C16—C21—C20	−1.1 (8)
C6—C7—C8—C9	−3.4 (7)	C15—C16—C21—C20	−179.2 (5)

Table 1

Selected bond lengths (Å)

Cu1—O1	1.874 (3)
Cu1—N1	2.011 (3)