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

In the title complex, [CuCl(2)(C(11)H(17)N(4)O(2))(2)], the Cu(II) ion, lying on an inversion center, is six-coordinated in a distorted octa-hedral [Cu(N(2)O(2)Cl(2))] 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 = 609.01

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.202

S = 1.06

3359 reflections

138 parameters

63 restraints

H-atom parameters constrained

Δρmax = 1.09 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040475/bh2382sup1.cif

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

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

[CuCl2(C11H17N4O2)2]	F(000) = 634
Mr = 609.01	Dx = 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

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

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(Fo2) + (0.116P)2 + 1.4099P] where P = (Fo2 + 2Fc2)/3
3359 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 1.09 e Å−3
63 restraints	Δρmin = −1.07 e Å−3

	x	y	z	Uiso*/Ueq	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)

	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)

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