Dichloridobis[4,4,5,5-tetra­methyl-2-(5-methyl-1H-imidazol-4-yl-κN3)-2-imidazoline-1-oxyl 3-oxide-κO]copper(II)

Gao, Z.Y.; Zhang, W.B.

doi:10.1107/S1600536811040475

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1504

doi:10.1107/S1600536811040475

Open

access

Dichloridobis[4,4,5,5-tetramethyl-2-(5-methyl-1H-imidazol-4-yl-κN³)-2-imidazoline-1-oxyl 3-oxide-κO]copper(II)

Zhi Yong Gao ^a ^* and Wen Bei Zhang ^a

^aCollege of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453002, People's Republic of China
^*Correspondence e-mail: gaozhy201@sohu.com

(Received 16 September 2011; accepted 1 October 2011; online 8 October 2011)

In the title complex, [CuCl₂(C₁₁H₁₇N₄O₂)₂], the Cu^II ion, lying on an inversion center, is six-coordinated in a distorted octahedral [Cu(N₂O₂Cl₂)] environment by two N,O-bidentate nitronyl nitroxide radical ligands and two trans-chloride anions. In the imidazoline-1-oxyl-3-oxide unit of the ligand, the four methyl groups and the C atoms to which they are bonded are disordered over two sets of sites, with a refined occupancy ratio of 0.737 (5):0.263 (5).

Related literature

For general background to molecular magnetic materials, see: Stroh et al. (2003 ); Kahn et al. (2000 ); Fursova et al. (2003 ). For complexes including nitronyl nitroxide ligands, see: Muppidi & Pal (2006 ); Wang et al. (2005 ); Gao et al. (2010 ). For the synthesis of the ligand of the title complex, see: Ullman et al. (1970 , 1972 ).

Experimental

Crystal data

[CuCl₂(C₁₁H₁₇N₄O₂)₂]
M_r = 609.01
Monoclinic, P 2₁ /c
a = 7.9966 (10) Å
b = 14.1981 (18) Å
c = 12.9266 (17) Å
β = 94.169 (3)°
V = 1463.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 295 K
0.43 × 0.27 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.682, T_max = 0.855
12447 measured reflections
3359 independent reflections
2607 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.202
S = 1.06
3359 reflections
138 parameters
63 restraints
H-atom parameters constrained
Δρ_max = 1.09 e Å⁻³
Δρ_min = −1.07 e Å⁻³

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811040475/bh2382sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040475/bh2382Isup2.hkl

checkCIF report

Comment top

The design and synthesis of molecule-based magnetic materials is one of the major subjects of material sciences (Stroh et al., 2003; Kahn et al., 2000; Fursova et al., 2003). In this field, nitronyl nitroxides acting as useful paramagnetic building blocks have been extensively used to assemble molecular magnetic materials due to their donor atoms and their ability to assemble extended arrangement with changing magnetic coupling (Muppidi et al., 2006; Wang et al., 2005; Gao et al., 2010). In this article, we report the synthesis and crystal structure of a novel Cu^II complex with nitronyl nitroxide radical.

The crystal structure of the title complex is shown in Figures 1 and 2. The copper(II) ion is six-coordinated in a slightly distorted octahedral CuN₂O₂Cl₂ environment. Two nitronyl nitroxide radicals, acting as bidentate chelating ligands, coordinate the Cu^II ion leading to two six-membered chelate rings, and the copper coordination is completed by two trans-arranged chloride anions.

Related literature top

For general background to molecular magnetic materials, see: Stroh et al. (2003); Kahn et al. (2000); Fursova et al. (2003). For complexes including nitronyl nitroxide ligands, see: Muppidi & Pal (2006); Wang et al. (2005); Gao et al. (2010). For the synthesis of the ligand of the title complex, see: Ullman et al. (1970, 1972).

Experimental top

The nitronyl nitroxide radical 4,4,5,5-tetramethyl-2-(5-methylimidazol-4-yl)-2-imidazoline-1-oxyl-3-oxide was prepared according to the literature method (Ullman et al., 1970, 1972). The complex was synthesized by mixing 3 ml of an ethanol solution of the radical ligand (0.6 mmol) and 5 ml of an ethanol solution of CuCl₂.2H₂O (0.3 mmol). After stirring for two hours at room temperature, the mixture solution was filtered. The clear deep purple filtrate was diffused with diethyl ether vapor at room temperature. Deep purple crystals suitable for X-ray analysis were obtained after a week.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP drawing of title compound, showing 30% probability displacement ellipsoids. (H atoms are omitted for clarity) [symmetry code A: -x, -y, -z +1]. All disordered atoms are present.
	Fig. 2. ORTEP drawing of the title compound omitting one set of disordered sites. Other features are as in Fig. 1.

Dichloridobis[4,4,5,5-tetramethyl-2-(5-methyl-1H-imidazol-4-yl- κN³)-2-imidazoline-1-oxyl 3-oxide-κO]copper(II) top

Crystal data top

[CuCl₂(C₁₁H₁₇N₄O₂)₂]	F(000) = 634
M_r = 609.01	D_x = 1.382 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5379 reflections
a = 7.9966 (10) Å	θ = 2.6–28.0°
b = 14.1981 (18) Å	µ = 0.97 mm⁻¹
c = 12.9266 (17) Å	T = 295 K
β = 94.169 (3)°	Block, deep purple
V = 1463.8 (3) Å³	0.43 × 0.27 × 0.17 mm
Z = 2

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3359 independent reflections
Radiation source: fine-focus sealed tube	2607 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
T_min = 0.682, T_max = 0.855	k = −18→18
12447 measured reflections	l = −16→16

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.202	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.116P)² + 1.4099P] where P = (F_o² + 2F_c²)/3
3359 reflections	(Δ/σ)_max < 0.001
138 parameters	Δρ_max = 1.09 e Å⁻³
63 restraints	Δρ_min = −1.07 e Å⁻³

Crystal data top

[CuCl₂(C₁₁H₁₇N₄O₂)₂]	V = 1463.8 (3) Å³
M_r = 609.01	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9966 (10) Å	µ = 0.97 mm⁻¹
b = 14.1981 (18) Å	T = 295 K
c = 12.9266 (17) Å	0.43 × 0.27 × 0.17 mm
β = 94.169 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3359 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2607 reflections with I > 2σ(I)
T_min = 0.682, T_max = 0.855	R_int = 0.027
12447 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	63 restraints
wR(F²) = 0.202	H-atom parameters constrained
S = 1.06	Δρ_max = 1.09 e Å⁻³
3359 reflections	Δρ_min = −1.07 e Å⁻³
138 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C5	0.0161 (3)	0.2896 (2)	0.4252 (2)	0.0550 (10)	0.737 (5)
C6	0.1823 (3)	0.3180 (2)	0.3766 (3)	0.0604 (15)	0.737 (5)
C7	−0.1329 (4)	0.2749 (4)	0.3473 (4)	0.093 (3)	0.737 (5)
H7A	−0.1087	0.2248	0.3008	0.140*	0.737 (5)
H7B	−0.1545	0.3318	0.3085	0.140*	0.737 (5)
H7C	−0.2297	0.2587	0.3834	0.140*	0.737 (5)
C8	−0.0353 (6)	0.3521 (3)	0.5121 (3)	0.086 (2)	0.737 (5)
H8A	−0.1245	0.3225	0.5460	0.130*	0.737 (5)
H8B	−0.0730	0.4117	0.4843	0.130*	0.737 (5)
H8C	0.0589	0.3617	0.5614	0.130*	0.737 (5)
C9	0.1879 (7)	0.2920 (4)	0.2629 (3)	0.107 (3)	0.737 (5)
H9A	0.3007	0.2977	0.2430	0.161*	0.737 (5)
H9B	0.1160	0.3335	0.2214	0.161*	0.737 (5)
H9C	0.1503	0.2282	0.2526	0.161*	0.737 (5)
C10	0.2323 (6)	0.4199 (3)	0.3906 (5)	0.108 (3)	0.737 (5)
H10A	0.2538	0.4333	0.4632	0.162*	0.737 (5)
H10B	0.1431	0.4596	0.3622	0.162*	0.737 (5)
H10C	0.3317	0.4319	0.3553	0.162*	0.737 (5)
C5'	0.02011 (18)	0.28092 (9)	0.40266 (12)	0.0550 (10)	0.263 (5)
C6'	0.1900 (2)	0.33754 (9)	0.41609 (13)	0.0604 (15)	0.263 (5)
C7'	−0.02440 (19)	0.24924 (10)	0.29180 (12)	0.093 (3)	0.263 (5)
H7'1	−0.0396	0.1822	0.2903	0.140*	0.263 (5)
H7'2	0.0646	0.2660	0.2493	0.140*	0.263 (5)
H7'3	−0.1263	0.2795	0.2657	0.140*	0.263 (5)
C8'	−0.1284 (2)	0.33251 (12)	0.44123 (15)	0.086 (2)	0.263 (5)
H8'1	−0.2221	0.2903	0.4420	0.130*	0.263 (5)
H8'2	−0.1574	0.3846	0.3960	0.130*	0.263 (5)
H8'3	−0.1002	0.3555	0.5101	0.130*	0.263 (5)
C9'	0.2417 (3)	0.38454 (12)	0.31841 (15)	0.107 (3)	0.263 (5)
H9'1	0.3429	0.4198	0.3339	0.161*	0.263 (5)
H9'2	0.1543	0.4262	0.2919	0.161*	0.263 (5)
H9'3	0.2610	0.3374	0.2674	0.161*	0.263 (5)
C10'	0.2082 (2)	0.40044 (10)	0.51042 (16)	0.108 (3)	0.263 (5)
H10D	0.2993	0.3784	0.5566	0.162*	0.263 (5)
H10E	0.1063	0.3991	0.5453	0.162*	0.263 (5)
H10F	0.2305	0.4638	0.4893	0.162*	0.263 (5)
Cu1	0.00000 (14)	0.00000 (9)	0.50000 (9)	0.0509 (3)
Cl1	0.13233 (14)	0.02450 (8)	0.29756 (8)	0.0751 (4)
O1	−0.04541 (13)	0.13931 (9)	0.50405 (9)	0.0500 (6)
O2	0.46321 (17)	0.25885 (10)	0.42078 (12)	0.0957 (12)
C1	0.31257 (11)	0.10914 (7)	0.54255 (7)	0.0410 (7)
C2	0.46835 (14)	0.10640 (9)	0.59493 (10)	0.0482 (8)
C3	0.34150 (18)	−0.02968 (9)	0.60589 (10)	0.0512 (8)
H3	0.3225	−0.0923	0.6225	0.061*
C4	0.23128 (11)	0.18575 (6)	0.48583 (8)	0.0423 (7)
C11	0.60017 (17)	0.17812 (12)	0.62182 (14)	0.0716 (12)
H11A	0.5963	0.1960	0.6932	0.107*
H11B	0.5809	0.2325	0.5785	0.107*
H11C	0.7084	0.1521	0.6110	0.107*
N1	0.23258 (13)	0.02450 (7)	0.55218 (8)	0.0426 (6)
N2	0.48285 (17)	0.01743 (10)	0.63320 (11)	0.0541 (8)
H2	0.5686	−0.0049	0.6690	0.065*
N3	0.06688 (12)	0.19728 (7)	0.47178 (9)	0.0416 (6)
N4	0.30710 (15)	0.25572 (8)	0.43551 (10)	0.0597 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C5	0.0462 (19)	0.047 (2)	0.071 (3)	0.0043 (16)	0.0012 (18)	0.016 (2)
C6	0.054 (2)	0.061 (3)	0.068 (4)	0.004 (2)	0.018 (2)	0.021 (3)
C7	0.064 (4)	0.103 (5)	0.109 (5)	−0.009 (4)	−0.024 (3)	0.058 (5)
C8	0.098 (5)	0.047 (3)	0.120 (6)	0.018 (3)	0.044 (4)	0.005 (3)
C9	0.105 (6)	0.152 (8)	0.069 (4)	0.021 (6)	0.026 (4)	0.039 (5)
C10	0.078 (4)	0.055 (4)	0.192 (10)	−0.011 (3)	0.017 (5)	0.020 (5)
C5'	0.0462 (19)	0.047 (2)	0.071 (3)	0.0043 (16)	0.0012 (18)	0.016 (2)
C6'	0.054 (2)	0.061 (3)	0.068 (4)	0.004 (2)	0.018 (2)	0.021 (3)
C7'	0.064 (4)	0.103 (5)	0.109 (5)	−0.009 (4)	−0.024 (3)	0.058 (5)
C8'	0.098 (5)	0.047 (3)	0.120 (6)	0.018 (3)	0.044 (4)	0.005 (3)
C9'	0.105 (6)	0.152 (8)	0.069 (4)	0.021 (6)	0.026 (4)	0.039 (5)
C10'	0.078 (4)	0.055 (4)	0.192 (10)	−0.011 (3)	0.017 (5)	0.020 (5)
Cu1	0.0331 (3)	0.0363 (3)	0.0801 (5)	0.0035 (2)	−0.0172 (3)	−0.0026 (3)
Cl1	0.0686 (7)	0.0770 (7)	0.0762 (7)	0.0088 (6)	−0.0188 (5)	−0.0067 (6)
O1	0.0322 (10)	0.0401 (13)	0.0783 (17)	0.0028 (9)	0.0084 (10)	0.0069 (11)
O2	0.0425 (16)	0.109 (3)	0.139 (3)	−0.0008 (17)	0.0273 (18)	0.035 (2)
C1	0.0298 (13)	0.0457 (17)	0.0472 (16)	0.0054 (12)	0.0004 (11)	−0.0064 (13)
C2	0.0319 (14)	0.056 (2)	0.0561 (19)	0.0057 (14)	0.0002 (13)	−0.0122 (15)
C3	0.0409 (18)	0.0487 (18)	0.062 (2)	0.0061 (15)	−0.0105 (15)	−0.0021 (16)
C4	0.0337 (14)	0.0451 (17)	0.0485 (17)	0.0016 (12)	0.0051 (12)	−0.0008 (13)
C11	0.0376 (18)	0.077 (3)	0.099 (3)	−0.0072 (19)	−0.0075 (19)	−0.019 (2)
N1	0.0354 (14)	0.0420 (13)	0.0493 (15)	0.0050 (11)	−0.0047 (11)	−0.0029 (11)
N2	0.0406 (15)	0.0618 (19)	0.0573 (17)	0.0129 (13)	−0.0132 (13)	−0.0074 (14)
N3	0.0324 (12)	0.0394 (14)	0.0533 (15)	0.0035 (10)	0.0057 (11)	0.0036 (11)
N4	0.0390 (15)	0.066 (2)	0.076 (2)	−0.0025 (14)	0.0132 (14)	0.0146 (17)

Geometric parameters (Å, º) top

C5—N3	1.487 (3)	C8'—H8'2	0.9600
C5—C8	1.5121	C8'—H8'3	0.9600
C5—C7	1.5170	C9'—H9'1	0.9600
C5—C6	1.5639	C9'—H9'2	0.9600
C6—N4	1.499 (3)	C9'—H9'3	0.9600
C6—C10	1.5086	C10'—H10D	0.9600
C6—C9	1.5189	C10'—H10E	0.9600
C7—H7A	0.9600	C10'—H10F	0.9600
C7—H7B	0.9600	Cu1—N1	1.9628
C7—H7C	0.9600	Cu1—N1ⁱ	1.963 (3)
C8—H8A	0.9600	Cu1—O1	2.0123
C8—H8B	0.9600	Cu1—O1ⁱ	2.012 (3)
C8—H8C	0.9600	Cu1—Cl1	2.9140
C9—H9A	0.9600	O1—N3	1.3086
C9—H9B	0.9600	O2—N4	1.2772
C9—H9C	0.9600	C1—N1	1.3713
C10—H10A	0.9600	C1—C2	1.3745
C10—H10B	0.9600	C1—C4	1.4401
C10—H10C	0.9600	C2—N2	1.3584
C5'—C8'	1.5106	C2—C11	1.4885
C5'—N3	1.5165	C3—N1	1.3208
C5'—C7'	1.5193	C3—N2	1.3385
C5'—C6'	1.5773	C3—H3	0.9300
C6'—N4	1.5016	C4—N3	1.3241
C6'—C10'	1.5099	C4—N4	1.3547
C6'—C9'	1.5121	C11—H11A	0.9600
C7'—H7'1	0.9600	C11—H11B	0.9600
C7'—H7'2	0.9600	C11—H11C	0.9600
C7'—H7'3	0.9600	N2—H2	0.8600
C8'—H8'1	0.9600

N3—C5—C8	107.3 (2)	H10E—C10'—H10F	109.5
N3—C5—C7	109.0 (2)	N1—Cu1—N1ⁱ	180.00 (11)
C8—C5—C7	109.3	N1—Cu1—O1	89.1
N3—C5—C6	100.09 (17)	N1ⁱ—Cu1—O1	90.85 (11)
C8—C5—C6	115.6	N1—Cu1—O1ⁱ	90.85 (9)
C7—C5—C6	114.7	N1ⁱ—Cu1—O1ⁱ	89.15 (9)
N4—C6—C10	110.1 (2)	O1—Cu1—O1ⁱ	180.00 (13)
N4—C6—C9	106.4 (2)	N1—Cu1—Cl1	83.7
C10—C6—C9	108.9	N1ⁱ—Cu1—Cl1	96.28 (10)
N4—C6—C5	101.38 (18)	O1—Cu1—Cl1	89.1
C10—C6—C5	115.1	O1ⁱ—Cu1—Cl1	90.91 (10)
C9—C6—C5	114.3	N3—O1—Cu1	118.7
C8'—C5'—N3	110.6	N1—C1—C2	110.0
C8'—C5'—C7'	108.6	N1—C1—C4	120.8
N3—C5'—C7'	110.8	C2—C1—C4	129.2
C8'—C5'—C6'	114.1	N2—C2—C1	104.8
N3—C5'—C6'	99.2	N2—C2—C11	120.7
C7'—C5'—C6'	113.3	C1—C2—C11	134.2
N4—C6'—C10'	107.5	N1—C3—N2	111.1
N4—C6'—C9'	106.0	N1—C3—H3	124.5
C10'—C6'—C9'	113.4	N2—C3—H3	124.5
N4—C6'—C5'	98.4	N3—C4—N4	108.5
C10'—C6'—C5'	115.0	N3—C4—C1	124.8
C9'—C6'—C5'	114.8	N4—C4—C1	126.7
C5'—C7'—H7'1	109.5	C2—C11—H11A	109.5
C5'—C7'—H7'2	109.5	C2—C11—H11B	109.5
H7'1—C7'—H7'2	109.5	H11A—C11—H11B	109.5
C5'—C7'—H7'3	109.5	C2—C11—H11C	109.5
H7'1—C7'—H7'3	109.5	H11A—C11—H11C	109.5
H7'2—C7'—H7'3	109.5	H11B—C11—H11C	109.5
C5'—C8'—H8'1	109.5	C3—N1—C1	105.3
C5'—C8'—H8'2	109.5	C3—N1—Cu1	130.5
H8'1—C8'—H8'2	109.5	C1—N1—Cu1	124.1
C5'—C8'—H8'3	109.5	C3—N2—C2	108.7
H8'1—C8'—H8'3	109.5	C3—N2—H2	125.7
H8'2—C8'—H8'3	109.5	C2—N2—H2	125.7
C6'—C9'—H9'1	109.5	O1—N3—C4	125.2
C6'—C9'—H9'2	109.5	O1—N3—C5	120.67 (12)
H9'1—C9'—H9'2	109.5	C4—N3—C5	113.83 (12)
C6'—C9'—H9'3	109.5	O1—N3—C5'	122.3
H9'1—C9'—H9'3	109.5	C4—N3—C5'	112.2
H9'2—C9'—H9'3	109.5	O2—N4—C4	125.0
C6'—C10'—H10D	109.5	O2—N4—C6	121.70 (12)
C6'—C10'—H10E	109.5	C4—N4—C6	111.83 (12)
H10D—C10'—H10E	109.5	O2—N4—C6'	123.5
C6'—C10'—H10F	109.5	C4—N4—C6'	110.6
H10D—C10'—H10F	109.5

N3—C5—C6—N4	−19.0 (2)	C1—C4—N3—O1	−2.6
C8—C5—C6—N4	95.9 (3)	N4—C4—N3—C5	−11.16 (16)
C7—C5—C6—N4	−135.5 (3)	C1—C4—N3—C5	170.75 (16)
N3—C5—C6—C10	−137.8 (2)	N4—C4—N3—C5'	2.0
C8—C5—C6—C10	−23.0	C1—C4—N3—C5'	−176.1
C7—C5—C6—C10	105.7	C8—C5—N3—O1	72.32 (16)
N3—C5—C6—C9	95.0 (2)	C7—C5—N3—O1	−45.98 (16)
C8—C5—C6—C9	−150.1	C6—C5—N3—O1	−166.68 (13)
C7—C5—C6—C9	−21.4	C8—C5—N3—C4	−101.31 (18)
C8'—C5'—C6'—N4	146.8	C7—C5—N3—C4	140.39 (17)
N3—C5'—C6'—N4	29.3	C6—C5—N3—C4	19.68 (19)
C7'—C5'—C6'—N4	−88.2	C8—C5—N3—C5'	173.9 (6)
C8'—C5'—C6'—C10'	33.0	C7—C5—N3—C5'	55.6 (5)
N3—C5'—C6'—C10'	−84.5	C6—C5—N3—C5'	−65.2 (5)
C7'—C5'—C6'—C10'	158.0	C8'—C5'—N3—O1	44.7
C8'—C5'—C6'—C9'	−101.1	C7'—C5'—N3—O1	−75.8
N3—C5'—C6'—C9'	141.3	C6'—C5'—N3—O1	164.9
C7'—C5'—C6'—C9'	23.8	C8'—C5'—N3—C4	−141.5
N1—Cu1—O1—N3	42.2	C7'—C5'—N3—C4	98.0
N1ⁱ—Cu1—O1—N3	−137.83 (10)	C6'—C5'—N3—C4	−21.3
Cl1—Cu1—O1—N3	−41.6	C8'—C5'—N3—C5	−41.2 (6)
N1—C1—C2—N2	2.1	C7'—C5'—N3—C5	−161.7 (6)
C4—C1—C2—N2	−179.4	C6'—C5'—N3—C5	79.0 (6)
N1—C1—C2—C11	−171.6	N3—C4—N4—O2	−169.8
C4—C1—C2—C11	6.9	C1—C4—N4—O2	8.3
N1—C1—C4—N3	25.7	N3—C4—N4—C6	−3.46 (17)
C2—C1—C4—N3	−152.7	C1—C4—N4—C6	174.59 (17)
N1—C1—C4—N4	−152.0	N3—C4—N4—C6'	20.5
C2—C1—C4—N4	29.5	C1—C4—N4—C6'	−161.5
N2—C3—N1—C1	2.0	C10—C6—N4—O2	−55.76 (15)
N2—C3—N1—Cu1	−174.8	C9—C6—N4—O2	62.09 (14)
C2—C1—N1—C3	−2.5	C5—C6—N4—O2	−178.12 (12)
C4—C1—N1—C3	178.8	C10—C6—N4—C4	137.42 (16)
C2—C1—N1—Cu1	174.6	C9—C6—N4—C4	−104.73 (17)
C4—C1—N1—Cu1	−4.1	C5—C6—N4—C4	15.1 (2)
O1—Cu1—N1—C3	153.7	C10—C6—N4—C6'	46.1 (3)
O1ⁱ—Cu1—N1—C3	−26.25 (10)	C9—C6—N4—C6'	163.9 (3)
Cl1—Cu1—N1—C3	−117.1	C5—C6—N4—C6'	−76.3 (3)
O1—Cu1—N1—C1	−22.6	C10'—C6'—N4—O2	−82.5
O1ⁱ—Cu1—N1—C1	157.41 (10)	C9'—C6'—N4—O2	39.1
Cl1—Cu1—N1—C1	66.6	C5'—C6'—N4—O2	157.9
N1—C3—N2—C2	−0.8	C10'—C6'—N4—C4	87.5
C1—C2—N2—C3	−0.8	C9'—C6'—N4—C4	−151.0
C11—C2—N2—C3	174.0	C5'—C6'—N4—C4	−32.1
Cu1—O1—N3—C4	−36.8	C10'—C6'—N4—C6	−175.1 (3)
Cu1—O1—N3—C5	150.33 (17)	C9'—C6'—N4—C6	−53.5 (3)
Cu1—O1—N3—C5'	136.2	C5'—C6'—N4—C6	65.3 (3)
N4—C4—N3—O1	175.5

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[CuCl₂(C₁₁H₁₇N₄O₂)₂]
M_r	609.01
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.9966 (10), 14.1981 (18), 12.9266 (17)
β (°)	94.169 (3)
V (Å³)	1463.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.43 × 0.27 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.682, 0.855
No. of measured, independent and observed [I > 2σ(I)] reflections	12447, 3359, 2607
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.202, 1.06
No. of reflections	3359
No. of parameters	138
No. of restraints	63
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.09, −1.07

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Acknowledgements

This work was supported by the Natural Science Foundation and Basic Research Program of Henan Province (Nos. 092300410195 and 092300410240).

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fursova, E. Y., Ovcharenko, V. I., Romanenko, G. V. & Tretyakov, E. V. (2003). Tetrahedron Lett. 44, 6397–6399. Web of Science CSD CrossRef CAS Google Scholar
Gao, Z. Y., Guo, H. J. & Zhang, W. B. (2010). Acta Cryst. E66, m19. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kahn, M. L., Sutter, J.-P., Golhen, S., Guionneau, P., Ouahab, L., Kahn, O. & Chasseau, D. (2000). J. Am. Chem. Soc. 122, 3413–3421. Web of Science CSD CrossRef CAS Google Scholar
Muppidi, V. K. & Pal, S. (2006). Eur. J. Inorg. Chem. pp. 2871–2877. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stroh, C., Belorizky, E., Turek, P., Bolvin, H. & Ziessel, R. (2003). Inorg. Chem. 42, 2938–2949. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ullman, E. F., Call, L. & Osiecki, J. H. (1970). J. Org. Chem. 35, 3623–3631. CrossRef CAS Web of Science Google Scholar
Ullman, E. F., Osiecki, J. H., Boocock, D. G. B. & Darcy, R. (1972). J. Am. Chem. Soc. 94, 7049–7059. CrossRef CAS Web of Science Google Scholar
Wang, L.-Y., Ma, L.-F., Jiang, Z.-H., Liao, D.-Z. & Yan, S.-P. (2005). Inorg. Chim. Acta, 358, 820–823. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.