Bis[1-(2-naphthyl­imino­meth­yl)-2-naphtholato-κ2N,O]copper(II)

Guo, Z.; Li, L.; Wang, C.; Li, J.; Xu, T.

doi:10.1107/S1600536809030694

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1049

doi:10.1107/S1600536809030694

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Bis[1-(2-naphthyliminomethyl)-2-naphtholato-κ²N,O]copper(II)

Zhenghua Guo,^a Lianzhi Li,^a ^* Chengyuan Wang,^b Jinghong Li ^a and Tao Xu ^a

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, and ^bResearch Center of Medical Chemistry and Chemical Biology, Chongqing Technology and Business University, Chongqing 400067, People's Republic of China
^*Correspondence e-mail: lilianzhi1963@yahoo.com.cn

(Received 10 July 2009; accepted 2 August 2009; online 8 August 2009)

In the title complex, [Cu(C₂₁H₁₄NO)₂], the Cu^II atom, lying on an inversion center, is coordinated by two bidentate 1-(2-naphthyliminomethyl)-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_r = 656.20
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.062
wR(F²) = 0.121
S = 1.10
2721 reflections
214 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.874 (3)
Cu1—N1	2.011 (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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030694/hy2212sup1.cif

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

checkCIF report

Comment top

Schiff base complexes play an important role in the stereochemical models of transition metal coordination chemistry, with their easy preparation, diversity and structural variation (Gamovski et al., 1993). They aslo have been intensively investigated owing to their strong coordination capability and diverse biological activities, such as antibacterial, and antitumor activities (Tarafder et al., 2002; Yang et al., 2000). As part of a series of the studies (Wang et al., 2007), we report here the synthesis and structure of the title compound, a new copper(II) complex with a bidentate Schiff base ligand derived from the condensation of 2-hydroxy-1-naphthyldehyde and 2-naphthylamine.

The molecular structure of the title complex is shown in Fig. 1. The Cu^II atom, lying on an inversion center, is coordinated by two bidentate ligands in a trans arrangement, forming a CuN₂O₂ square-planar configuration (Table 1), with the typical values of Cu—O and Cu—N bond lengths (Unver et al., 2003). The mean planes of the chelate ring N1, C1, C2, C3, O1, Cu1 (A), bicycles C2—C11 (B) and C12—C21 (C) make the following dihedral angles: A/B 18.92 (19), A/C 58.14 (12) and B/C 40.32 (11)°. Additionally, the relatively short intermolecular distance H12···C7ⁱ (symmetry code: (i) x + 1, y, z) of 2.90Å indicates the possible prescence of C—H···π interaction, which forms a one-dimensional chain structure (Fig. 2).

Related literature top

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 top

2-Naphthylamine(0.143 g, 1 mmol) was dissolved in hot methanol (10 ml) and added dropwise to a methanol solution (3 ml) of 2-hydroxy-1-naphthyldehyde (0.172 g, 1 mmol). The mixture was then stirred at 323 K for 2 h. Subsequently, an aqueous solution (2 ml) of cupric acetate hydrate (0.200 g, 1 mmol) was added dropwise and stirred for another 5 h. The solution was held at room temperature for 15 d, whereupon green needle crystals suitable for X-ray diffraction were obtained.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) -x + 1, -y + 1, -z + 1].
	Fig. 2. One-dimensional chain structure of the title compound, connected by weak C—H···π interactions (dashed lines).

Bis[1-(2-naphthyliminomethyl)-2-naphtholato-κ²N,O]copper(II) top

Crystal data top

[Cu(C₂₁H₁₄NO)₂]	F(000) = 678
M_r = 656.20	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.P)² + 3.3732P] where P = (F_o² + 2F_c²)/3
2721 reflections	(Δ/σ)_max < 0.001
214 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.75 e Å⁻³

Crystal data top

[Cu(C₂₁H₁₄NO)₂]	V = 1549.4 (12) Å³
M_r = 656.20	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.648 (3) Å	µ = 0.75 mm⁻¹
b = 18.578 (8) Å	T = 298 K
c = 14.796 (6) Å	0.35 × 0.10 × 0.04 mm
β = 93.635 (5)°

Data collection top

Bruker SMART 1000 CCD diffractometer	2721 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1869 reflections with I > 2σ(I)
T_min = 0.780, T_max = 0.971	R_int = 0.062
7695 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.10	Δρ_max = 0.47 e Å⁻³
2721 reflections	Δρ_min = −0.75 e Å⁻³
214 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₂₁H₁₄NO)₂]
M_r	656.20
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	5.648 (3), 18.578 (8), 14.796 (6)
β (°)	93.635 (5)
V (Å³)	1549.4 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.35 × 0.10 × 0.04

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.780, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	7695, 2721, 1869
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.121, 1.10
No. of reflections	2721
No. of parameters	214
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.75

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O1

1.874 (3)

Cu1—N1

2.011 (3)

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province (No. Y2004B02) for a research grant.

References

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