Bis[μ-N′-isobutyryl-1-oxidonaphtha­lene-2-carbohydrazidato(3-)]dipyridine­tricopper(II)

Shi, X.-F.; Li, D.; Li, P.-Y.; Wang, D.-Q.

doi:10.1107/S1600536809009003

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m435

doi:10.1107/S1600536809009003

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Bis[μ-N′-isobutyryl-1-oxidonaphthalene-2-carbohydrazidato(3-)]dipyridinetricopper(II)

Xue-Feng Shi,^a Dacheng Li,^a ^* Pi-Yong Li ^a and Da-Qi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: lidacheng@lcu.edu.cn

(Received 20 February 2009; accepted 11 March 2009; online 25 March 2009)

The complete molecule of the title complex, [Cu₃(C₁₅H₁₃N₂O₃)₂(C₅H₅N)₂], is generated by crystallographic twofold symmetry, with the central Cu atom lying on the rotation axis: it is coordinated by two N,O-bidentate ligands in a trans-CuN₂O₂ distorted square-planar arrangement. The other Cu atom is coordinated by an N,O,O′-tridentate ligand and a pyridine molecule in a distorted trans-CuN₂O₂ arrangement. In the crystal structure, a C—H⋯π interaction occurs.

Related literature

For related structures, see: Patole et al. (2003 ); Pouralimardan et al. (2007 ). For background on C—H⋯π interactions, see: Nishio (2004 ); Saalfrank & Bernt (1998 ).

Experimental

Crystal data

[Cu₃(C₁₅H₁₃N₂O₃)₂(C₅H₅N)₂]
M_r = 887.37
Monoclinic, C 2/c
a = 23.661 (2) Å
b = 13.0521 (18) Å
c = 13.3142 (15) Å
β = 113.684 (2)°
V = 3765.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.74 mm⁻¹
T = 298 K
0.37 × 0.35 × 0.31 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996 ) T_min = 0.566, T_max = 0.615 (expected range = 0.537–0.584)
9477 measured reflections
3310 independent reflections
2319 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.135
S = 1.00
3310 reflections
251 parameters
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.920 (3)
Cu1—O1ⁱ	1.920 (3)
Cu1—N2	1.946 (3)
Cu1—N2ⁱ	1.946 (3)
Cu2—N1	1.884 (3)
Cu2—O2	1.890 (3)
Cu2—O3	1.953 (3)
Cu2—N3	1.975 (3)
Symmetry code: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯Cg1ⁱⁱ	0.93	2.53	3.362 (4)	150
Symmetry code: (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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 I, global. DOI: 10.1107/S1600536809009003/hb2917sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009003/hb2917Isup2.hkl

checkCIF report

Comment top

A large number of aroylhydrazine complexes have been prepared and studied due to their diverse molecular architectures and quite interesting chemical properties (Patole et al., 2003; Pouralimardan et al., 2007). However, researches on the copper(II) complexes with N-isobutyryl-1-hydroxy-2-naphthalenecarbohydrazide have not reported. So we have synthesized a new complex, (I), (Fig. 1), which has been characterized by X-ray diffraction and elemental analysis. The molecule of (I) contains three copper(II), two ligand molecules, and two pyridine molecules. Both copper centres adopt distorted square planar trans-CuN₂O₂ arrangements. The triple-deprotonated N-isobutyryl-1-hydroxy-2-naphthalenecarbohydrazide bridges the metal ions using a hydrazide N—N group and formed the trinuclear copper complex. In the crystal packing, the complex molecules are linked into two-dimensional network by intermolecular C—H···π interactions (Fig. 2) (Saalfrank & Bernt, 1998; Nishio, 2004).

Related literature top

For related structures, see: Patole et al. (2003); Pouralimardan et al. (2007). For background on C—H···π interactions, see: Nishio (2004); Saalfrank & Bernt (1998). Cg1 is the centroid of the C2–C7 ring.

Experimental top

Isobutyric anhydride (0.632 g, 4 mmol) and 1-hydroxy-2-naphthalenecarbohydrazide (0.808 g, 4 mmol) were added to 40 ml of chloroform at ice-water bath. The reaction mixture was slowly warmed to room temperature and stirred for 24 h. After overnight refrigeration, the resulting white precipitate was filtered and rinsed with chloroform and diethyl ether (1.02 g, 93.57% yield). A solution of CuNO₃(0.04 g,0.2 mmol) in methanol (10 ml) was added to a mixture of N-isobutyryl-1-hydroxy-2-naphthalenecarbohydrazide (0.055 g, 0.2 mmol) and sodium methylate (0.0324 g, 0.6 mmol) in pyridine (10 ml). A green solution was obtained after refluxing for 3 h. After being filtrated, dimethyl ether was slowly diffused into the filtrate, and green blocks of (I) were obtained after two weeks. Elemental analysis calculated for C₄₀H₃₆N₆O₆Cu₃: C, 54.09; H, 4.05; O, 10.78; N, 9.43. Found (%): C, 54.12; H, 4.06; O, 10.82; N, 9.47

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (I) showing 40% probability displacement ellipsoids. H atoms have been omitted for clarity. Symmetry code: (i) 1–x, y, 1/2–z.
	Fig. 2. View of the two-dimensional network structure in (I). Intermolecular C—H···π are shown as dashed lines. Most of H atoms are omitted.

Bis[µ-N'-isobutyryl-1-oxidonaphthalene-2- carbohydrazidato(3-)]dipyridinetricopper(II) top

Crystal data top

[Cu₃(C₁₅H₁₃N₂O₃)₂(C₅H₅N)₂]	F(000) = 1812
M_r = 887.37	D_x = 1.565 Mg m⁻³ D_m = 1.565 Mg m⁻³ D_m measured by not measured
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3140 reflections
a = 23.661 (2) Å	θ = 2.7–26.3°
b = 13.0521 (18) Å	µ = 1.74 mm⁻¹
c = 13.3142 (15) Å	T = 298 K
β = 113.684 (2)°	Block, green
V = 3765.5 (7) Å³	0.37 × 0.35 × 0.31 mm
Z = 4

Data collection top

Siemens SMART CCD diffractometer	3310 independent reflections
Radiation source: fine-focus sealed tube	2319 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −28→27
T_min = 0.566, T_max = 0.615	k = −14→15
9477 measured reflections	l = −13→15

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.079P)² + 4.0071P] where P = (F_o² + 2F_c²)/3
3310 reflections	(Δ/σ)_max = 0.001
251 parameters	Δρ_max = 0.82 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Cu₃(C₁₅H₁₃N₂O₃)₂(C₅H₅N)₂]	V = 3765.5 (7) Å³
M_r = 887.37	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 23.661 (2) Å	µ = 1.74 mm⁻¹
b = 13.0521 (18) Å	T = 298 K
c = 13.3142 (15) Å	0.37 × 0.35 × 0.31 mm
β = 113.684 (2)°

Data collection top

Siemens SMART CCD diffractometer	3310 independent reflections
Absorption correction: multi-scan (SADABS; Siemens, 1996)	2319 reflections with I > 2σ(I)
T_min = 0.566, T_max = 0.615	R_int = 0.050
9477 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.00	Δρ_max = 0.82 e Å⁻³
3310 reflections	Δρ_min = −0.33 e Å⁻³
251 parameters

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

	x	y	z	U_iso*/U_eq
Cu1	0.5000	0.86302 (6)	0.2500	0.0410 (2)
Cu2	0.68569 (2)	0.80745 (4)	0.23216 (4)	0.0404 (2)
N1	0.62147 (15)	0.8496 (3)	0.2723 (3)	0.0401 (8)
N2	0.56137 (15)	0.8380 (3)	0.1900 (3)	0.0425 (9)
N3	0.74587 (15)	0.7504 (3)	0.1787 (3)	0.0386 (8)
O1	0.57183 (12)	0.8896 (2)	0.3816 (2)	0.0446 (7)
O2	0.74777 (12)	0.8431 (2)	0.3698 (2)	0.0442 (7)
O3	0.61596 (13)	0.7851 (3)	0.0920 (2)	0.0523 (8)
C1	0.62281 (18)	0.8758 (3)	0.3692 (3)	0.0363 (9)
C2	0.73934 (18)	0.8742 (3)	0.4567 (3)	0.0361 (9)
C3	0.68203 (18)	0.8912 (3)	0.4623 (3)	0.0341 (9)
C4	0.68036 (19)	0.9281 (3)	0.5618 (3)	0.0399 (10)
H4	0.6421	0.9386	0.5645	0.048*
C5	0.7314 (2)	0.9484 (3)	0.6518 (3)	0.0440 (11)
H5	0.7278	0.9733	0.7144	0.053*
C6	0.7909 (2)	0.9322 (3)	0.6522 (3)	0.0421 (10)
C7	0.79500 (19)	0.8936 (3)	0.5546 (3)	0.0398 (10)
C8	0.85377 (19)	0.8776 (4)	0.5545 (4)	0.0503 (11)
H8	0.8570	0.8522	0.4919	0.060*
C9	0.9059 (2)	0.8990 (5)	0.6448 (4)	0.0674 (15)
H9	0.9443	0.8885	0.6426	0.081*
C10	0.9026 (2)	0.9367 (4)	0.7415 (4)	0.0655 (15)
H10	0.9385	0.9507	0.8029	0.079*
C11	0.8464 (2)	0.9522 (4)	0.7439 (4)	0.0559 (13)
H11	0.8443	0.9767	0.8080	0.067*
C12	0.56432 (19)	0.8035 (4)	0.0990 (4)	0.0451 (11)
C13	0.5056 (2)	0.7872 (4)	−0.0027 (4)	0.0548 (13)
H13	0.4703	0.7944	0.0176	0.066*
C14	0.5046 (3)	0.6793 (5)	−0.0479 (5)	0.090 (2)
H14A	0.5318	0.6765	−0.0854	0.135*
H14B	0.4634	0.6627	−0.0982	0.135*
H14C	0.5180	0.6310	0.0114	0.135*
C15	0.5004 (3)	0.8681 (5)	−0.0879 (5)	0.0862 (19)
H15A	0.5084	0.9344	−0.0539	0.129*
H15B	0.4595	0.8668	−0.1449	0.129*
H15C	0.5299	0.8541	−0.1188	0.129*
C16	0.7284 (2)	0.6777 (3)	0.0995 (3)	0.0414 (10)
H16	0.6872	0.6577	0.0689	0.050*
C17	0.7684 (2)	0.6324 (3)	0.0624 (4)	0.0468 (11)
H17	0.7548	0.5822	0.0084	0.056*
C18	0.8288 (2)	0.6624 (4)	0.1064 (4)	0.0585 (13)
H18	0.8571	0.6324	0.0829	0.070*
C19	0.8476 (2)	0.7379 (5)	0.1861 (4)	0.0604 (13)
H19	0.8883	0.7605	0.2160	0.072*
C20	0.8046 (2)	0.7787 (4)	0.2200 (4)	0.0489 (11)
H20	0.8174	0.8285	0.2745	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0270 (4)	0.0562 (5)	0.0400 (4)	0.000	0.0138 (3)	0.000
Cu2	0.0282 (3)	0.0537 (4)	0.0391 (3)	−0.0004 (2)	0.0133 (2)	−0.0070 (2)
N1	0.0243 (17)	0.058 (2)	0.0350 (19)	−0.0019 (16)	0.0083 (15)	−0.0053 (17)
N2	0.0269 (18)	0.062 (2)	0.0371 (19)	−0.0036 (17)	0.0110 (16)	−0.0097 (18)
N3	0.0349 (19)	0.044 (2)	0.0392 (19)	0.0012 (16)	0.0175 (16)	−0.0024 (17)
O1	0.0286 (15)	0.0644 (19)	0.0435 (17)	−0.0017 (14)	0.0172 (13)	−0.0100 (15)
O2	0.0308 (15)	0.0602 (19)	0.0417 (17)	−0.0003 (14)	0.0146 (13)	−0.0083 (15)
O3	0.0291 (16)	0.088 (2)	0.0386 (17)	0.0002 (16)	0.0123 (13)	−0.0135 (16)
C1	0.031 (2)	0.039 (2)	0.041 (2)	−0.0013 (18)	0.0161 (18)	−0.0011 (19)
C2	0.034 (2)	0.032 (2)	0.040 (2)	−0.0022 (17)	0.0121 (18)	0.0006 (18)
C3	0.029 (2)	0.034 (2)	0.037 (2)	−0.0010 (17)	0.0120 (17)	−0.0024 (18)
C4	0.039 (2)	0.042 (2)	0.040 (2)	−0.0004 (19)	0.016 (2)	−0.0016 (19)
C5	0.057 (3)	0.041 (2)	0.034 (2)	−0.003 (2)	0.017 (2)	−0.0002 (19)
C6	0.046 (3)	0.032 (2)	0.041 (2)	−0.0017 (19)	0.011 (2)	0.0039 (19)
C7	0.040 (2)	0.032 (2)	0.043 (2)	−0.0017 (18)	0.013 (2)	0.0008 (19)
C8	0.034 (2)	0.059 (3)	0.053 (3)	0.002 (2)	0.012 (2)	−0.008 (2)
C9	0.037 (3)	0.089 (4)	0.066 (3)	0.001 (3)	0.009 (3)	−0.006 (3)
C10	0.041 (3)	0.072 (4)	0.058 (3)	−0.002 (3)	−0.007 (2)	−0.004 (3)
C11	0.057 (3)	0.054 (3)	0.043 (3)	−0.003 (2)	0.006 (2)	−0.002 (2)
C12	0.031 (2)	0.064 (3)	0.040 (2)	−0.001 (2)	0.0130 (19)	−0.001 (2)
C13	0.031 (2)	0.088 (4)	0.038 (2)	0.001 (2)	0.008 (2)	−0.009 (3)
C14	0.078 (4)	0.082 (4)	0.070 (4)	−0.011 (3)	−0.012 (3)	−0.016 (3)
C15	0.074 (4)	0.084 (4)	0.064 (4)	−0.006 (3)	−0.009 (3)	0.004 (3)
C16	0.042 (2)	0.038 (2)	0.044 (2)	−0.0023 (19)	0.018 (2)	0.001 (2)
C17	0.056 (3)	0.040 (3)	0.046 (3)	0.004 (2)	0.022 (2)	−0.002 (2)
C18	0.057 (3)	0.070 (3)	0.055 (3)	0.024 (3)	0.031 (3)	0.002 (3)
C19	0.035 (3)	0.089 (4)	0.056 (3)	0.005 (3)	0.017 (2)	−0.003 (3)
C20	0.035 (2)	0.062 (3)	0.047 (3)	0.000 (2)	0.014 (2)	−0.008 (2)

Geometric parameters (Å, º) top

Cu1—O1	1.920 (3)	C8—C9	1.361 (6)
Cu1—O1ⁱ	1.920 (3)	C8—H8	0.9300
Cu1—N2	1.946 (3)	C9—C10	1.409 (7)
Cu1—N2ⁱ	1.946 (3)	C9—H9	0.9300
Cu2—N1	1.884 (3)	C10—C11	1.360 (7)
Cu2—O2	1.890 (3)	C10—H10	0.9300
Cu2—O3	1.953 (3)	C11—H11	0.9300
Cu2—N3	1.975 (3)	C12—C13	1.516 (6)
N1—C1	1.323 (5)	C13—C15	1.518 (8)
N1—N2	1.412 (5)	C13—C14	1.529 (8)
N2—C12	1.320 (5)	C13—H13	0.9800
N3—C20	1.326 (5)	C14—H14A	0.9600
N3—C16	1.354 (5)	C14—H14B	0.9600
O1—C1	1.294 (5)	C14—H14C	0.9600
O2—C2	1.315 (5)	C15—H15A	0.9600
O3—C12	1.285 (5)	C15—H15B	0.9600
C1—C3	1.465 (5)	C15—H15C	0.9600
C2—C3	1.405 (5)	C16—C17	1.365 (6)
C2—C7	1.455 (6)	C16—H16	0.9300
C3—C4	1.425 (6)	C17—C18	1.367 (7)
C4—C5	1.342 (6)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.384 (7)
C5—C6	1.423 (6)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.374 (6)
C6—C11	1.412 (6)	C19—H19	0.9300
C6—C7	1.433 (6)	C20—H20	0.9300
C7—C8	1.406 (6)

O1—Cu1—O1ⁱ	159.21 (19)	C7—C8—H8	119.5
O1—Cu1—N2	82.65 (13)	C8—C9—C10	121.0 (5)
O1ⁱ—Cu1—N2	100.87 (13)	C8—C9—H9	119.5
O1—Cu1—N2ⁱ	100.87 (13)	C10—C9—H9	119.5
O1ⁱ—Cu1—N2ⁱ	82.65 (13)	C11—C10—C9	119.2 (4)
N2—Cu1—N2ⁱ	160.7 (2)	C11—C10—H10	120.4
N1—Cu2—O2	93.11 (13)	C9—C10—H10	120.4
N1—Cu2—O3	81.17 (13)	C10—C11—C6	122.0 (5)
O2—Cu2—O3	173.00 (13)	C10—C11—H11	119.0
N1—Cu2—N3	172.94 (14)	C6—C11—H11	119.0
O2—Cu2—N3	92.88 (13)	O3—C12—N2	122.2 (4)
O3—Cu2—N3	93.10 (13)	O3—C12—C13	117.8 (4)
C1—N1—N2	114.0 (3)	N2—C12—C13	120.0 (4)
C1—N1—Cu2	130.2 (3)	C12—C13—C15	109.9 (4)
N2—N1—Cu2	115.1 (3)	C12—C13—C14	110.1 (4)
C12—N2—N1	109.9 (3)	C15—C13—C14	111.2 (5)
C12—N2—Cu1	139.2 (3)	C12—C13—H13	108.5
N1—N2—Cu1	110.4 (2)	C15—C13—H13	108.5
C20—N3—C16	117.3 (4)	C14—C13—H13	108.5
C20—N3—Cu2	122.2 (3)	C13—C14—H14A	109.5
C16—N3—Cu2	120.4 (3)	C13—C14—H14B	109.5
C1—O1—Cu1	112.8 (3)	H14A—C14—H14B	109.5
C2—O2—Cu2	126.6 (3)	C13—C14—H14C	109.5
C12—O3—Cu2	111.4 (3)	H14A—C14—H14C	109.5
O1—C1—N1	120.1 (4)	H14B—C14—H14C	109.5
O1—C1—C3	119.8 (4)	C13—C15—H15A	109.5
N1—C1—C3	120.1 (3)	C13—C15—H15B	109.5
O2—C2—C3	125.9 (4)	H15A—C15—H15B	109.5
O2—C2—C7	116.0 (4)	C13—C15—H15C	109.5
C3—C2—C7	118.1 (4)	H15A—C15—H15C	109.5
C2—C3—C4	119.4 (4)	H15B—C15—H15C	109.5
C2—C3—C1	123.3 (4)	N3—C16—C17	123.1 (4)
C4—C3—C1	117.3 (3)	N3—C16—H16	118.5
C5—C4—C3	123.1 (4)	C17—C16—H16	118.5
C5—C4—H4	118.5	C16—C17—C18	118.6 (4)
C3—C4—H4	118.5	C16—C17—H17	120.7
C4—C5—C6	120.6 (4)	C18—C17—H17	120.7
C4—C5—H5	119.7	C17—C18—C19	119.4 (4)
C6—C5—H5	119.7	C17—C18—H18	120.3
C11—C6—C5	123.4 (4)	C19—C18—H18	120.3
C11—C6—C7	118.2 (4)	C20—C19—C18	118.4 (5)
C5—C6—C7	118.4 (4)	C20—C19—H19	120.8
C8—C7—C6	118.6 (4)	C18—C19—H19	120.8
C8—C7—C2	120.9 (4)	N3—C20—C19	123.2 (4)
C6—C7—C2	120.5 (4)	N3—C20—H20	118.4
C9—C8—C7	121.0 (5)	C19—C20—H20	118.4
C9—C8—H8	119.5

O2—Cu2—N1—C1	−10.5 (4)	N1—C1—C3—C4	174.6 (4)
O3—Cu2—N1—C1	173.6 (4)	C2—C3—C4—C5	0.4 (6)
O2—Cu2—N1—N2	179.6 (3)	C1—C3—C4—C5	−177.8 (4)
O3—Cu2—N1—N2	3.6 (3)	C3—C4—C5—C6	−0.9 (7)
C1—N1—N2—C12	−174.6 (4)	C4—C5—C6—C11	179.9 (4)
Cu2—N1—N2—C12	−3.0 (5)	C4—C5—C6—C7	−0.1 (6)
C1—N1—N2—Cu1	−0.9 (5)	C11—C6—C7—C8	−0.1 (6)
Cu2—N1—N2—Cu1	170.69 (17)	C5—C6—C7—C8	179.8 (4)
O1—Cu1—N2—C12	172.5 (5)	C11—C6—C7—C2	−178.4 (4)
O1ⁱ—Cu1—N2—C12	−28.3 (5)	C5—C6—C7—C2	1.6 (6)
N2ⁱ—Cu1—N2—C12	70.6 (5)	O2—C2—C7—C8	−1.0 (6)
O1—Cu1—N2—N1	1.6 (3)	C3—C2—C7—C8	179.8 (4)
O1ⁱ—Cu1—N2—N1	160.8 (3)	O2—C2—C7—C6	177.1 (4)
N2ⁱ—Cu1—N2—N1	−100.4 (3)	C3—C2—C7—C6	−2.1 (6)
O2—Cu2—N3—C20	−23.5 (4)	C6—C7—C8—C9	−0.4 (7)
O3—Cu2—N3—C20	152.8 (4)	C2—C7—C8—C9	177.8 (5)
O2—Cu2—N3—C16	154.6 (3)	C7—C8—C9—C10	0.7 (8)
O3—Cu2—N3—C16	−29.1 (3)	C8—C9—C10—C11	−0.3 (9)
O1ⁱ—Cu1—O1—C1	−103.3 (3)	C9—C10—C11—C6	−0.3 (8)
N2—Cu1—O1—C1	−2.0 (3)	C5—C6—C11—C10	−179.4 (5)
N2ⁱ—Cu1—O1—C1	158.7 (3)	C7—C6—C11—C10	0.5 (7)
N1—Cu2—O2—C2	6.4 (3)	Cu2—O3—C12—N2	3.1 (6)
N3—Cu2—O2—C2	−169.9 (3)	Cu2—O3—C12—C13	−178.6 (3)
N1—Cu2—O3—C12	−3.6 (3)	N1—N2—C12—O3	−0.2 (6)
N3—Cu2—O3—C12	172.2 (3)	Cu1—N2—C12—O3	−171.2 (3)
Cu1—O1—C1—N1	2.2 (5)	N1—N2—C12—C13	−178.4 (4)
Cu1—O1—C1—C3	−179.0 (3)	Cu1—N2—C12—C13	10.7 (8)
N2—N1—C1—O1	−0.8 (6)	O3—C12—C13—C15	−69.6 (6)
Cu2—N1—C1—O1	−170.8 (3)	N2—C12—C13—C15	108.6 (5)
N2—N1—C1—C3	−179.6 (3)	O3—C12—C13—C14	53.2 (6)
Cu2—N1—C1—C3	10.4 (6)	N2—C12—C13—C14	−128.5 (5)
Cu2—O2—C2—C3	−3.0 (6)	C20—N3—C16—C17	0.9 (6)
Cu2—O2—C2—C7	177.9 (3)	Cu2—N3—C16—C17	−177.3 (3)
O2—C2—C3—C4	−178.1 (4)	N3—C16—C17—C18	−0.7 (7)
C7—C2—C3—C4	1.1 (6)	C16—C17—C18—C19	−0.5 (7)
O2—C2—C3—C1	0.1 (7)	C17—C18—C19—C20	1.4 (8)
C7—C2—C3—C1	179.2 (4)	C16—N3—C20—C19	0.0 (7)
O1—C1—C3—C2	177.6 (4)	Cu2—N3—C20—C19	178.2 (4)
N1—C1—C3—C2	−3.6 (6)	C18—C19—C20—N3	−1.2 (8)
O1—C1—C3—C4	−4.3 (6)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg1ⁱⁱ	0.93	2.53	3.362 (4)	150

Symmetry code: (ii) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu₃(C₁₅H₁₃N₂O₃)₂(C₅H₅N)₂]
M_r	887.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	23.661 (2), 13.0521 (18), 13.3142 (15)
β (°)	113.684 (2)
V (Å³)	3765.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.74
Crystal size (mm)	0.37 × 0.35 × 0.31

Data collection
Diffractometer	Siemens SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.566, 0.615
No. of measured, independent and observed [I > 2σ(I)] reflections	9477, 3310, 2319
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.135, 1.00
No. of reflections	3310
No. of parameters	251
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.33

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O1	1.920 (3)	Cu2—N1	1.884 (3)
Cu1—O1ⁱ	1.920 (3)	Cu2—O2	1.890 (3)
Cu1—N2	1.946 (3)	Cu2—O3	1.953 (3)
Cu1—N2ⁱ	1.946 (3)	Cu2—N3	1.975 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg1ⁱⁱ	0.93	2.53	3.362 (4)	150

Symmetry code: (ii) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

We acknowledge financial support from the National Natural Science Foundation of China (grant No. 20671048).

References

Nishio, M. (2004). CrystEngComm, 6, 130–158. Web of Science CrossRef CAS Google Scholar
Patole, J., Sandbhor, U., Padhye, S., Deobagkar, D. N., Anson, C. E. & Powell, A. (2003). Bioorg. Med. Chem. Lett. 13, 51–55. Web of Science CSD CrossRef PubMed CAS Google Scholar
Pouralimardan, O., Chamayou, A. C., Janiak, C. & Hassan, H. M. (2007). Inorg. Chim. Acta, 360, 1599–1608. Web of Science CSD CrossRef CAS Google Scholar
Saalfrank, R. W. & Bernt, I. (1998). Curr. Opin. Solid State Mater. Sci. 3, 407–413. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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Volume 65| Part 4| April 2009| Page m435

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis[μ-N′-isobutyryl-1-oxidonaphtha­lene-2-carbohydrazidato(3-)]di­pyridine­tricopper(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[μ-N′-isobutyryl-1-oxidonaphthalene-2-carbohydrazidato(3-)]dipyridinetricopper(II)