Di-μ-chlorido-bis­(chlorido{2,2′-[3-(1H-imidazol-4-ylmeth­yl)-3-aza­pentane-1,5-di­yl]diphthalimide}copper(II))

Qi, Z.-P.; Wang, A.-D.; Zhang, H.; Wang, X.-X.

doi:10.1107/S1600536809045565

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1507-m1508

doi:10.1107/S1600536809045565

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Di-μ-chlorido-bis(chlorido{2,2′-[3-(1H-imidazol-4-ylmethyl)-3-azapentane-1,5-diyl]diphthalimide}copper(II))

Zhao-Peng Qi,^a ^* Ai-Dong Wang,^a Hui Zhang ^a and Xi-Xi Wang ^a

^aDepartment of Chemistry, Huangshan University, Huangshan 245041, People's Republic of China
^*Correspondence e-mail: zhaopengqi@hsu.edu.cn

(Received 11 October 2009; accepted 29 October 2009; online 4 November 2009)

The centrosymmetric dinuclear Cu^II complex, [Cu₂Cl₄(C₂₄H₂₁N₅O₄)₂], was synthesized by the reaction of CuCl₂·2H₂O with the tripodal ligand 2,2′-[3-(1H-imidazol-4-ylmethyl)-3-azapentane-1,5-diyl]diphthalimide (L). Each of the Cu^II ions is coordinated by two N atoms from the ligand, two bridging Cl atoms and one terminal Cl atom. The Cu^II coordination can be best be described as a transition state between four- and five-coordination, since one of the bridging Cl atoms has a much longer Cu—Cl bond distance [2.7069 (13) Å] than the other [2.2630 (12) Å]. In addition, the Cu⋯Cu distance is 3.622 (1) Å. The three-dimensional structrure is generated by N—H⋯O, C—H⋯O and C—H⋯Cl hydrogen bonds and π–π interactions [centroid–centroid distances = 3.658 (4) and 4.020 (4) Å].

Related literature

For the synthesis, see: Qi et al. (2008 ). For the use of imidazole-containing tripodal ligands in supramolecular chemistry and new functional materials, see: Higa et al. (2007 ); Kong et al. (2005 ); Katsuki et al. (2002 ). For a related structure with a similar coordination geometry around the metal atom, see: Yu et al. (2009 ).

Experimental

Crystal data

[Cu₂Cl₄(C₂₄H₂₁N₅O₄)₂]
M_r = 1155.80
Monoclinic, P 2₁ /c
a = 8.4351 (9) Å
b = 14.6867 (16) Å
c = 20.1448 (19) Å
β = 105.593 (4)°
V = 2403.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.17 mm⁻¹
T = 293 K
0.2 × 0.1 × 0.1 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.86, T_max = 0.89
11745 measured reflections
4218 independent reflections
3394 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.150
S = 1.17
4218 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N2	1.932 (4)
Cu1—N1	2.211 (4)
Cu1—Cl1	2.2431 (15)
Cu1—Cl2ⁱ	2.2630 (12)
Cu1—Cl2	2.7069 (13)
Symmetry code: (i) -x+2, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O3ⁱⁱ	0.86	2.37	3.022 (6)	133
C3—H3B⋯Cl1ⁱⁱⁱ	0.93	2.65	3.445 (6)	144
C4—H4A⋯O2ⁱⁱ	0.93	2.45	3.131 (7)	131
C6—H6B⋯O2	0.97	2.51	2.870 (7)	102
C15—H15A⋯Cl1ⁱ	0.97	2.82	3.769 (5)	165
C20—H20A⋯O1^iv	0.93	2.53	3.218 (9)	131
Symmetry codes: (i) -x+2, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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/S1600536809045565/kp2236sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045565/kp2236Isup2.hkl

checkCIF report

Comment top

In recent years, imidazole-containing tripodal ligands have attracted much attention for their extensive use in supramolecular chemistry and new functional materials (Higa, et al., 2007; Kong et al., 2005; Katsuki, et al., 2002). Here, we synthesized a new tripodal ligand L, 3-(imidazole-4-yl-methyl)-1,5-diphthalimido-3-azapentane, and reported its Cu^II complex.

In this complex, the Cu^II ion is coordinated by two N atoms from the ligand, two bridging Cl atoms and one terminal Cl atom. The two bridging Cl atoms are quite different, the equatorial Cl atom exbits a Cu—Cl distance of 2.2630 (12) Å, while that of the axial Cl atom is much longer with 2.7069 (13) Å (Table 1). Thus, the Cu^II coordination can be better described as a transition state between 4 and 5 coordination. In addition, the Cu—Cu distance is about 3.622 Å. A dimer of two monomeric units bridged by two chlorido ions reveals an inversion centre in the middle of the molecule (Fig. 1). The dimers are further connected to form the three-dimensional packing by N—H···O, C—H···O, C—H···Cl hydrogen-bonds and π–π interactions involving neighbouring phthalamide rings [Cg1···Cg2(-x+2,y+1/2,-z+1/2) = 3.658 (4) and Cg1···Cg3(-x+1,y+1/2,-z+1/2 = 4.020 (4) Å where Cg1, Cg2 and Cg2 are the centroids of the N5/C17/C18/C23/C24, C18–C23 and N4/C7/C8/C13/C14 rings, respectively (Fig. 2)].

Related literature top

For the synthesis, see: Qi et al. (2008). For the use of imidazole-containing tripodal ligands in supramolecular chemistry and new functional materials, see: Higa et al. (2007); Kong et al. (2005); Katsuki et al. (2002). For a related structure with a simiar coordination geometry around the metal atom, see: Yu et al. (2009).

Experimental top

The tripodal ligand L, 3-(imidazole-4-yl-methyl)-1,5-diphthalimido-3-azapentane, was synthesized by a literature method (Qi et al., 2008). The title complex was synthesized as follows: a methanol solution (3 ml) of L (36.3 mg, 0.1 mmol) was added to a CH₃CN solution (2 ml) of CuCl₂.2H₂O (17.0 mg, 0.1 mmol). Green crystals were obtained by slow evaporation of the solution in air for several days.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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) with atom labelling and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The three-dimensional packing of (I) viewed down the b axisrealized by N—H···O, C—H···O, C—H···Cl hydrogen-bonds (dashed lines) and π–π interactions.

Di-µ-chlorido-bis(chlorido{2,2'-[3-(1H-imidazol-4-ylmethyl)-3- azapentane-1,5-diyl]diphthalimide}copper(II)) top

Crystal data top

[Cu₂Cl₄(C₂₄H₂₁N₅O₄)₂]	F(000) = 1180
M_r = 1155.80	D_x = 1.597 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1643 reflections
a = 8.4351 (9) Å	θ = 2.5–21.3°
b = 14.6867 (16) Å	µ = 1.17 mm⁻¹
c = 20.1448 (19) Å	T = 293 K
β = 105.593 (4)°	Block, green
V = 2403.8 (4) Å³	0.2 × 0.1 × 0.1 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	4218 independent reflections
Radiation source: fine-focus sealed tube	3394 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.86, T_max = 0.89	k = −17→9
11745 measured reflections	l = −22→23

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0656P)² + 0.075P] where P = (F_o² + 2F_c²)/3
4218 reflections	(Δ/σ)_max = 0.001
325 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³
0 constraints

Crystal data top

[Cu₂Cl₄(C₂₄H₂₁N₅O₄)₂]	V = 2403.8 (4) Å³
M_r = 1155.80	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4351 (9) Å	µ = 1.17 mm⁻¹
b = 14.6867 (16) Å	T = 293 K
c = 20.1448 (19) Å	0.2 × 0.1 × 0.1 mm
β = 105.593 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4218 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3394 reflections with I > 2σ(I)
T_min = 0.86, T_max = 0.89	R_int = 0.047
11745 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.17	Δρ_max = 0.61 e Å⁻³
4218 reflections	Δρ_min = −0.30 e Å⁻³
325 parameters

Special details top

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.

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 > σ(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.

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

	x	y	z	U_iso*/U_eq
Cu1	0.93018 (7)	0.11519 (4)	0.50753 (3)	0.0346 (2)
Cl1	1.12292 (17)	0.19333 (11)	0.58499 (8)	0.0620 (4)
Cl2	0.89142 (14)	−0.05739 (8)	0.54767 (6)	0.0369 (3)
O1	0.7721 (7)	0.4237 (3)	0.4369 (2)	0.0851 (15)
O2	0.9233 (5)	0.2868 (3)	0.26250 (19)	0.0620 (11)
O3	0.6332 (6)	0.1249 (3)	0.1982 (2)	0.0799 (14)
O4	0.5644 (5)	−0.1647 (3)	0.2630 (2)	0.0696 (12)
N1	0.7125 (5)	0.1113 (2)	0.41720 (19)	0.0331 (9)
N2	0.7596 (5)	0.1576 (3)	0.54753 (19)	0.0371 (9)
N3	0.5988 (6)	0.2086 (3)	0.6073 (2)	0.0573 (13)
H3A	0.5670	0.2339	0.6400	0.069*
N4	0.8396 (5)	0.3347 (3)	0.3553 (2)	0.0426 (10)
N5	0.6000 (5)	−0.0116 (3)	0.2470 (2)	0.0445 (10)
C1	0.5748 (6)	0.0876 (3)	0.4473 (2)	0.0372 (11)
H1A	0.4704	0.1049	0.4158	0.045*
H1B	0.5733	0.0225	0.4553	0.045*
C2	0.6000 (6)	0.1372 (3)	0.5129 (3)	0.0374 (12)
C3	0.4990 (7)	0.1690 (4)	0.5504 (3)	0.0496 (14)
H3B	0.3849	0.1645	0.5392	0.060*
C4	0.7537 (7)	0.2019 (4)	0.6041 (3)	0.0517 (14)
H4A	0.8446	0.2250	0.6368	0.062*
C5	0.6910 (6)	0.2056 (3)	0.3885 (3)	0.0395 (12)
H5A	0.6333	0.2423	0.4146	0.047*
H5B	0.6248	0.2037	0.3410	0.047*
C6	0.8551 (6)	0.2485 (3)	0.3918 (3)	0.0489 (14)
H6A	0.9144	0.2582	0.4396	0.059*
H6B	0.9193	0.2069	0.3720	0.059*
C7	0.8081 (7)	0.4161 (4)	0.3837 (3)	0.0510 (14)
C8	0.8283 (6)	0.4883 (3)	0.3344 (2)	0.0424 (12)
C9	0.8152 (8)	0.5819 (4)	0.3369 (3)	0.0586 (16)
H9A	0.7858	0.6107	0.3730	0.070*
C10	0.8480 (8)	0.6310 (4)	0.2832 (3)	0.0598 (16)
H10A	0.8419	0.6942	0.2835	0.072*
C11	0.8889 (7)	0.5882 (4)	0.2298 (3)	0.0557 (15)
H11A	0.9083	0.6232	0.1943	0.067*
C12	0.9023 (7)	0.4950 (4)	0.2270 (3)	0.0484 (13)
H12A	0.9306	0.4664	0.1906	0.058*
C13	0.8722 (6)	0.4459 (3)	0.2804 (3)	0.0410 (12)
C14	0.8824 (6)	0.3467 (3)	0.2942 (3)	0.0412 (12)
C15	0.7243 (6)	0.0443 (3)	0.3632 (2)	0.0383 (12)
H15A	0.7659	−0.0126	0.3857	0.046*
H15B	0.8046	0.0665	0.3405	0.046*
C16	0.5645 (6)	0.0249 (4)	0.3085 (3)	0.0477 (13)
H16A	0.4994	−0.0186	0.3261	0.057*
H16B	0.5013	0.0806	0.2971	0.057*
C17	0.6355 (7)	0.0435 (4)	0.1965 (3)	0.0555 (15)
C18	0.6740 (7)	−0.0193 (4)	0.1452 (3)	0.0559 (15)
C19	0.7175 (9)	−0.0007 (5)	0.0860 (3)	0.083 (2)
H19A	0.7253	0.0587	0.0711	0.099*
C20	0.7496 (10)	−0.0755 (7)	0.0492 (3)	0.089 (2)
H20A	0.7801	−0.0659	0.0086	0.107*
C21	0.7373 (8)	−0.1627 (6)	0.0710 (4)	0.075 (2)
H21A	0.7602	−0.2112	0.0454	0.090*
C22	0.6916 (7)	−0.1796 (5)	0.1305 (3)	0.0638 (17)
H22A	0.6835	−0.2390	0.1453	0.077*
C23	0.6583 (7)	−0.1073 (4)	0.1675 (3)	0.0506 (14)
C24	0.6043 (7)	−0.1033 (4)	0.2314 (3)	0.0504 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0370 (4)	0.0344 (4)	0.0361 (4)	0.0013 (3)	0.0159 (3)	−0.0045 (3)
Cl1	0.0480 (8)	0.0709 (11)	0.0690 (10)	−0.0078 (7)	0.0189 (7)	−0.0349 (8)
Cl2	0.0405 (7)	0.0386 (7)	0.0359 (7)	0.0054 (5)	0.0173 (5)	0.0011 (5)
O1	0.145 (5)	0.064 (3)	0.068 (3)	0.003 (3)	0.067 (3)	0.005 (2)
O2	0.099 (3)	0.039 (2)	0.054 (2)	0.013 (2)	0.031 (2)	−0.0029 (19)
O3	0.123 (4)	0.044 (3)	0.076 (3)	−0.005 (3)	0.031 (3)	0.005 (2)
O4	0.094 (3)	0.056 (3)	0.063 (3)	−0.016 (2)	0.029 (2)	0.002 (2)
N1	0.040 (2)	0.030 (2)	0.034 (2)	0.0029 (17)	0.0180 (18)	0.0043 (17)
N2	0.038 (2)	0.043 (2)	0.034 (2)	0.0052 (19)	0.0167 (19)	−0.0045 (19)
N3	0.067 (3)	0.064 (3)	0.050 (3)	0.016 (3)	0.031 (3)	−0.010 (2)
N4	0.055 (3)	0.028 (2)	0.048 (3)	−0.001 (2)	0.021 (2)	0.008 (2)
N5	0.059 (3)	0.039 (3)	0.034 (2)	−0.007 (2)	0.011 (2)	−0.004 (2)
C1	0.036 (3)	0.036 (3)	0.042 (3)	−0.007 (2)	0.014 (2)	0.005 (2)
C2	0.044 (3)	0.034 (3)	0.042 (3)	0.004 (2)	0.024 (2)	0.007 (2)
C3	0.049 (3)	0.052 (4)	0.055 (4)	0.010 (3)	0.025 (3)	0.007 (3)
C4	0.058 (4)	0.056 (4)	0.044 (3)	0.006 (3)	0.018 (3)	−0.011 (3)
C5	0.046 (3)	0.036 (3)	0.040 (3)	0.006 (2)	0.019 (2)	0.005 (2)
C6	0.052 (3)	0.036 (3)	0.058 (4)	0.000 (2)	0.014 (3)	0.016 (3)
C7	0.066 (4)	0.046 (3)	0.047 (3)	0.000 (3)	0.026 (3)	0.009 (3)
C8	0.056 (3)	0.034 (3)	0.041 (3)	0.000 (2)	0.019 (3)	0.002 (2)
C9	0.093 (5)	0.035 (3)	0.053 (4)	−0.007 (3)	0.028 (3)	−0.006 (3)
C10	0.088 (5)	0.027 (3)	0.066 (4)	−0.009 (3)	0.023 (4)	0.003 (3)
C11	0.074 (4)	0.045 (4)	0.053 (4)	−0.008 (3)	0.024 (3)	0.015 (3)
C12	0.068 (4)	0.042 (3)	0.041 (3)	−0.005 (3)	0.026 (3)	0.005 (3)
C13	0.053 (3)	0.028 (3)	0.043 (3)	−0.006 (2)	0.015 (2)	0.001 (2)
C14	0.056 (3)	0.032 (3)	0.036 (3)	0.000 (2)	0.013 (2)	0.001 (2)
C15	0.045 (3)	0.034 (3)	0.040 (3)	−0.001 (2)	0.018 (2)	−0.006 (2)
C16	0.047 (3)	0.053 (4)	0.043 (3)	0.000 (3)	0.012 (2)	−0.006 (3)
C17	0.067 (4)	0.046 (4)	0.048 (3)	−0.001 (3)	0.006 (3)	0.003 (3)
C18	0.066 (4)	0.062 (4)	0.038 (3)	−0.005 (3)	0.011 (3)	−0.004 (3)
C19	0.118 (6)	0.080 (5)	0.058 (4)	−0.005 (5)	0.037 (4)	0.010 (4)
C20	0.107 (6)	0.123 (7)	0.044 (4)	−0.010 (5)	0.033 (4)	−0.012 (5)
C21	0.066 (4)	0.097 (6)	0.066 (5)	−0.009 (4)	0.023 (4)	−0.031 (4)
C22	0.057 (4)	0.065 (4)	0.063 (4)	−0.007 (3)	0.005 (3)	−0.018 (3)
C23	0.051 (3)	0.049 (4)	0.047 (3)	−0.005 (3)	0.005 (3)	−0.008 (3)
C24	0.055 (3)	0.052 (4)	0.041 (3)	−0.009 (3)	0.008 (3)	−0.006 (3)

Geometric parameters (Å, º) top

Cu1—N2	1.932 (4)	C5—H5B	0.9700
Cu1—N1	2.211 (4)	C6—H6A	0.9700
Cu1—Cl1	2.2431 (15)	C6—H6B	0.9700
Cu1—Cl2ⁱ	2.2630 (12)	C7—C8	1.493 (7)
Cu1—Cl2	2.7069 (13)	C8—C9	1.382 (7)
Cl2—Cu1ⁱ	2.2630 (12)	C8—C13	1.386 (7)
O1—C7	1.196 (6)	C9—C10	1.389 (8)
O2—C14	1.192 (6)	C9—H9A	0.9300
O3—C17	1.198 (6)	C10—C11	1.368 (8)
O4—C24	1.202 (6)	C10—H10A	0.9300
N1—C1	1.489 (5)	C11—C12	1.376 (7)
N1—C15	1.489 (5)	C11—H11A	0.9300
N1—C5	1.492 (6)	C12—C13	1.375 (6)
N2—C4	1.325 (6)	C12—H12A	0.9300
N2—C2	1.373 (6)	C13—C14	1.481 (7)
N3—C4	1.329 (6)	C15—C16	1.522 (7)
N3—C3	1.358 (7)	C15—H15A	0.9700
N3—H3A	0.8600	C15—H15B	0.9700
N4—C7	1.382 (7)	C16—H16A	0.9700
N4—C14	1.383 (6)	C16—H16B	0.9700
N4—C6	1.452 (6)	C17—C18	1.485 (8)
N5—C24	1.385 (7)	C18—C19	1.366 (7)
N5—C17	1.392 (7)	C18—C23	1.387 (8)
N5—C16	1.453 (6)	C19—C20	1.393 (10)
C1—C2	1.472 (7)	C19—H19A	0.9300
C1—H1A	0.9700	C20—C21	1.367 (10)
C1—H1B	0.9700	C20—H20A	0.9300
C2—C3	1.364 (6)	C21—C22	1.377 (8)
C3—H3B	0.9300	C21—H21A	0.9300
C4—H4A	0.9300	C22—C23	1.368 (8)
C5—C6	1.506 (6)	C22—H22A	0.9300
C5—H5A	0.9700	C23—C24	1.479 (7)

N2—Cu1—N1	78.75 (15)	N4—C7—C8	105.7 (4)
N2—Cu1—Cl1	91.52 (13)	C9—C8—C13	121.1 (5)
N1—Cu1—Cl1	150.69 (11)	C9—C8—C7	131.1 (5)
N2—Cu1—Cl2ⁱ	173.87 (13)	C13—C8—C7	107.8 (5)
N1—Cu1—Cl2ⁱ	95.78 (10)	C8—C9—C10	116.9 (5)
Cl1—Cu1—Cl2ⁱ	94.61 (5)	C8—C9—H9A	121.5
N2—Cu1—Cl2	90.81 (12)	C10—C9—H9A	121.5
N1—Cu1—Cl2	94.67 (10)	C11—C10—C9	121.3 (5)
Cl1—Cu1—Cl2	113.23 (6)	C11—C10—H10A	119.3
Cl2ⁱ—Cu1—Cl2	86.86 (4)	C9—C10—H10A	119.3
Cu1ⁱ—Cl2—Cu1	93.14 (4)	C10—C11—C12	122.0 (5)
C1—N1—C15	110.8 (4)	C10—C11—H11A	119.0
C1—N1—C5	110.3 (3)	C12—C11—H11A	119.0
C15—N1—C5	110.8 (3)	C13—C12—C11	117.1 (5)
C1—N1—Cu1	103.7 (3)	C13—C12—H12A	121.5
C15—N1—Cu1	114.5 (3)	C11—C12—H12A	121.5
C5—N1—Cu1	106.4 (3)	C12—C13—C8	121.5 (5)
C4—N2—C2	106.6 (4)	C12—C13—C14	130.5 (5)
C4—N2—Cu1	136.2 (4)	C8—C13—C14	108.0 (4)
C2—N2—Cu1	117.1 (3)	O2—C14—N4	124.4 (5)
C4—N3—C3	108.8 (4)	O2—C14—C13	129.5 (5)
C4—N3—H3A	125.6	N4—C14—C13	106.1 (4)
C3—N3—H3A	125.6	N1—C15—C16	115.7 (4)
C7—N4—C14	112.5 (4)	N1—C15—H15A	108.4
C7—N4—C6	123.2 (4)	C16—C15—H15A	108.4
C14—N4—C6	123.5 (4)	N1—C15—H15B	108.4
C24—N5—C17	112.1 (4)	C16—C15—H15B	108.4
C24—N5—C16	125.1 (4)	H15A—C15—H15B	107.4
C17—N5—C16	122.8 (5)	N5—C16—C15	110.0 (4)
C2—C1—N1	108.0 (4)	N5—C16—H16A	109.7
C2—C1—H1A	110.1	C15—C16—H16A	109.7
N1—C1—H1A	110.1	N5—C16—H16B	109.7
C2—C1—H1B	110.1	C15—C16—H16B	109.7
N1—C1—H1B	110.1	H16A—C16—H16B	108.2
H1A—C1—H1B	108.4	O3—C17—N5	123.4 (6)
C3—C2—N2	108.4 (5)	O3—C17—C18	130.4 (6)
C3—C2—C1	134.8 (5)	N5—C17—C18	106.1 (5)
N2—C2—C1	116.8 (4)	C19—C18—C23	122.7 (6)
N3—C3—C2	106.1 (5)	C19—C18—C17	130.1 (6)
N3—C3—H3B	127.0	C23—C18—C17	107.2 (5)
C2—C3—H3B	127.0	C18—C19—C20	116.3 (7)
N2—C4—N3	110.1 (5)	C18—C19—H19A	121.8
N2—C4—H4A	125.0	C20—C19—H19A	121.8
N3—C4—H4A	125.0	C21—C20—C19	121.7 (6)
N1—C5—C6	110.9 (4)	C21—C20—H20A	119.2
N1—C5—H5A	109.5	C19—C20—H20A	119.2
C6—C5—H5A	109.5	C20—C21—C22	120.8 (7)
N1—C5—H5B	109.5	C20—C21—H21A	119.6
C6—C5—H5B	109.5	C22—C21—H21A	119.6
H5A—C5—H5B	108.0	C23—C22—C21	118.7 (7)
N4—C6—C5	112.7 (4)	C23—C22—H22A	120.7
N4—C6—H6A	109.0	C21—C22—H22A	120.7
C5—C6—H6A	109.0	C22—C23—C18	119.8 (5)
N4—C6—H6B	109.0	C22—C23—C24	131.4 (6)
C5—C6—H6B	109.0	C18—C23—C24	108.8 (5)
H6A—C6—H6B	107.8	O4—C24—N5	125.6 (5)
O1—C7—N4	125.1 (5)	O4—C24—C23	128.8 (5)
O1—C7—C8	129.2 (5)	N5—C24—C23	105.6 (5)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O3ⁱⁱ	0.86	2.37	3.022 (6)	133
C3—H3B···Cl1ⁱⁱⁱ	0.93	2.65	3.445 (6)	144
C4—H4A···O2ⁱⁱ	0.93	2.45	3.131 (7)	131
C6—H6B···O2	0.97	2.51	2.870 (7)	102
C15—H15A···Cl1ⁱ	0.97	2.82	3.769 (5)	165
C20—H20A···O1^iv	0.93	2.53	3.218 (9)	131

Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) x−1, y, z; (iv) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Cu₂Cl₄(C₂₄H₂₁N₅O₄)₂]
M_r	1155.80
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.4351 (9), 14.6867 (16), 20.1448 (19)
β (°)	105.593 (4)
V (Å³)	2403.8 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.17
Crystal size (mm)	0.2 × 0.1 × 0.1

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.86, 0.89
No. of measured, independent and observed [I > 2σ(I)] reflections	11745, 4218, 3394
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.150, 1.17
No. of reflections	4218
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.30

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—N2	1.932 (4)	Cu1—Cl2ⁱ	2.2630 (12)
Cu1—N1	2.211 (4)	Cu1—Cl2	2.7069 (13)
Cu1—Cl1	2.2431 (15)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O3ⁱⁱ	0.86	2.37	3.022 (6)	133
C3—H3B···Cl1ⁱⁱⁱ	0.93	2.65	3.445 (6)	144
C4—H4A···O2ⁱⁱ	0.93	2.45	3.131 (7)	131
C6—H6B···O2	0.97	2.51	2.870 (7)	102
C15—H15A···Cl1ⁱ	0.97	2.82	3.769 (5)	165
C20—H20A···O1^iv	0.93	2.53	3.218 (9)	131

Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) x−1, y, z; (iv) x, −y+1/2, z−1/2.

Acknowledgements

This work was supported by the Project of Huangshan University (2008xkjq020).

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Higa, T., Moriya, M., Shimazaki, Y., Yajima, T., Tani, F., Karasawa, S., Nakano, M., Naruta, Y. & Yamauchi, O. (2007). Inorg. Chim. Acta, 360, 3304–3313. Web of Science CSD CrossRef CAS Google Scholar
Katsuki, I., Motoda, Y., Sunatsuki, Y., Matsumoto, N., Nakashima, T. & Kojima, M. (2002). J. Am. Chem. Soc. 124, 629–640. Web of Science CSD CrossRef PubMed CAS Google Scholar
Kong, L.-Y., Zhang, Z.-H., Zhu, H.-F., Kawaguchi, H., Okamura, T., Doi, M., Chu, Q., Sun, W.-Y. & Ueyama, N. (2005). Angew. Chem. Int. Ed. 44, 4352–4355. Web of Science CSD CrossRef CAS Google Scholar
Qi, Z.-P., Bai, Z.-S., Yuan, Q., Okamura, T., Cai, K., Su, Z., Sun, W.-Y. & Ueyama, N. (2008). Polyhedron, 27, 2672–2680. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, M.-M., Shi, Q.-Z., Zhang, Y.-N. & Li, Z.-X. (2009). Acta Cryst. E65, m744–m745. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 12| December 2009| Pages m1507-m1508

doi:10.1107/S1600536809045565

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

Di-μ-chlorido-bis­­(chlorido{2,2′-[3-(1H-imidazol-4-ylmeth­yl)-3-aza­pentane-1,5-di­yl]diphthalimide}copper(II))

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Di-μ-chlorido-bis(chlorido{2,2′-[3-(1H-imidazol-4-ylmethyl)-3-azapentane-1,5-diyl]diphthalimide}copper(II))