Dibromidobis[1-(2-bromo-benz-yl)-3-(pyrimidin-2-yl)-1H-imidazol-2(3H)-one]copper(II).

In the title complex, [CuBr(2)(C(14)H(11)BrN(4)O)(2)], the Cu(II) ion is located on an inversion centre and is coordinated by two ketonic O atoms, two N atoms and two Br atoms, forming a distorted octahedral coordination environment. The two carbonyl groups are trans positioned with C=O bond lengths of 1.256 (5) Å, in agreement with a classical carbonyl bond. The Cu-O bond length is 2.011 (3) Å. The two bromo-benzyl rings are approximately parallel to one another, forming a dihedral angle of 70.1 (4)° with the coordination plane.

Related literature

For general background, see: Moncol et al. (2008 ▶); Wu et al. (2003 ▶); Anbu & Kandaswamy (2012 ▶). For related structures, see: Citadelle et al. (2010 ▶); Liu et al. (2011 ▶); Marjani et al. (2005 ▶); Meghdadi et al. (2012 ▶).

Experimental

Crystal data

[CuBr2(C14H11BrN4O)2]

M = 885.72

Monoclinic,

a = 8.6803 (11) Å

b = 23.0354 (8) Å

c = 7.8543 (9) Å

β = 109.419 (1)°

V = 1481.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 6.18 mm−1

T = 298 K

0.43 × 0.30 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.177, T max = 0.479

7275 measured reflections

2622 independent reflections

2019 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.117

S = 1.01

2622 reflections

196 parameters

H-atom parameters constrained

Δρmax = 1.31 e Å−3

Δρmin = −0.90 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021460/ru2034sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812021460/ru2034Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021460/ru2034Isup2.hkl

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

[CuBr2(C14H11BrN4O)2]	F(000) = 862
Mr = 885.72	Dx = 1.986 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.6803 (11) Å	Cell parameters from 7275 reflections
b = 23.0354 (8) Å	θ = 1.8–25.1°
c = 7.8543 (9) Å	µ = 6.18 mm−1
β = 109.419 (1)°	T = 298 K
V = 1481.2 (3) Å3	Block, yellow
Z = 2	0.43 × 0.30 × 0.14 mm

Bruker SMART CCD area-detector diffractometer	2622 independent reflections
Radiation source: fine-focus sealed tube	2019 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
phi and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→8
Tmin = 0.177, Tmax = 0.479	k = −27→20
7275 measured reflections	l = −9→8

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0654P)2] where P = (Fo2 + 2Fc2)/3
2622 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 1.31 e Å−3
0 restraints	Δρmin = −0.90 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.5000	0.5000	0.0270 (3)
N1	0.7847 (4)	0.41135 (18)	0.7064 (5)	0.0240 (9)
N2	0.6658 (4)	0.37501 (18)	0.8889 (5)	0.0245 (9)
N3	0.6973 (5)	0.46886 (18)	0.4448 (5)	0.0240 (9)
N4	0.9437 (5)	0.41415 (19)	0.5252 (6)	0.0307 (11)
Br1	0.68599 (7)	0.22945 (3)	1.05716 (9)	0.0525 (2)
Br2	0.70578 (6)	0.54952 (2)	0.82796 (7)	0.0343 (2)
O1	0.5017 (4)	0.42702 (15)	0.6410 (4)	0.0271 (8)
C1	0.6372 (5)	0.4069 (2)	0.7368 (6)	0.0249 (11)
C2	0.8315 (6)	0.3607 (2)	0.9542 (7)	0.0308 (13)
H2	0.8821	0.3393	1.0582	0.037*
C3	0.9052 (6)	0.3822 (2)	0.8467 (7)	0.0300 (12)
H3	1.0154	0.3788	0.8603	0.036*
C4	0.8100 (6)	0.4324 (2)	0.5504 (7)	0.0242 (11)
C5	0.9699 (6)	0.4335 (2)	0.3762 (8)	0.0372 (14)
H5	1.0654	0.4226	0.3557	0.045*
C6	0.8598 (6)	0.4692 (2)	0.2517 (7)	0.0342 (13)
H6	0.8773	0.4814	0.1467	0.041*
C7	0.7231 (6)	0.4854 (2)	0.2919 (7)	0.0286 (12)
H7	0.6457	0.5088	0.2104	0.034*
C8	0.5415 (6)	0.3582 (2)	0.9661 (7)	0.0295 (12)
H8A	0.4736	0.3916	0.9664	0.035*
H8B	0.5946	0.3464	1.0905	0.035*
C9	0.4349 (6)	0.3096 (2)	0.8659 (7)	0.0295 (12)
C10	0.4763 (6)	0.2516 (3)	0.8917 (7)	0.0344 (13)
C11	0.3759 (8)	0.2078 (3)	0.8035 (9)	0.0502 (17)
H11	0.4089	0.1693	0.8262	0.060*
C12	0.2274 (8)	0.2208 (3)	0.6820 (10)	0.058 (2)
H12	0.1585	0.1911	0.6207	0.070*
C13	0.1780 (7)	0.2780 (3)	0.6490 (9)	0.0559 (19)
H13	0.0767	0.2868	0.5648	0.067*
C14	0.2800 (6)	0.3221 (3)	0.7416 (8)	0.0414 (15)
H14	0.2455	0.3605	0.7213	0.050*

	U11	U22	U33	U12	U13	U23
Cu1	0.0258 (4)	0.0231 (5)	0.0378 (5)	0.0072 (4)	0.0181 (4)	0.0100 (4)
N1	0.023 (2)	0.023 (2)	0.028 (2)	0.0032 (18)	0.0107 (17)	0.0006 (19)
N2	0.027 (2)	0.022 (2)	0.026 (2)	−0.0005 (19)	0.0111 (17)	0.0003 (19)
N3	0.027 (2)	0.021 (2)	0.025 (2)	0.0001 (19)	0.0106 (18)	0.0016 (19)
N4	0.026 (2)	0.032 (3)	0.040 (3)	0.004 (2)	0.0180 (19)	0.002 (2)
Br1	0.0517 (4)	0.0387 (4)	0.0715 (5)	0.0133 (3)	0.0262 (3)	0.0235 (3)
Br2	0.0355 (3)	0.0329 (4)	0.0373 (4)	0.0010 (2)	0.0158 (2)	−0.0018 (2)
O1	0.0232 (17)	0.0231 (19)	0.037 (2)	0.0054 (15)	0.0129 (15)	0.0114 (16)
C1	0.027 (3)	0.025 (3)	0.025 (3)	−0.002 (2)	0.011 (2)	0.000 (2)
C2	0.029 (3)	0.034 (3)	0.027 (3)	0.004 (2)	0.006 (2)	0.006 (2)
C3	0.023 (2)	0.035 (3)	0.032 (3)	0.005 (2)	0.008 (2)	0.004 (3)
C4	0.027 (2)	0.018 (3)	0.031 (3)	−0.003 (2)	0.014 (2)	−0.004 (2)
C5	0.033 (3)	0.037 (4)	0.050 (4)	−0.001 (3)	0.025 (3)	−0.007 (3)
C6	0.042 (3)	0.034 (3)	0.035 (3)	−0.001 (3)	0.023 (3)	−0.005 (3)
C7	0.029 (3)	0.025 (3)	0.032 (3)	0.001 (2)	0.010 (2)	−0.002 (2)
C8	0.037 (3)	0.028 (3)	0.029 (3)	0.003 (3)	0.017 (2)	0.003 (2)
C9	0.035 (3)	0.027 (3)	0.034 (3)	−0.002 (2)	0.021 (2)	0.007 (2)
C10	0.034 (3)	0.034 (3)	0.042 (3)	0.000 (3)	0.021 (2)	0.003 (3)
C11	0.058 (4)	0.034 (4)	0.074 (5)	−0.012 (3)	0.042 (4)	−0.008 (3)
C12	0.055 (4)	0.055 (5)	0.073 (5)	−0.030 (4)	0.033 (4)	−0.027 (4)
C13	0.033 (3)	0.078 (6)	0.056 (4)	−0.013 (4)	0.014 (3)	−0.002 (4)
C14	0.037 (3)	0.047 (4)	0.046 (3)	0.002 (3)	0.022 (3)	0.006 (3)

Cu1—O1i	2.011 (3)	C3—H3	0.9300
Cu1—O1	2.011 (3)	C5—C6	1.387 (8)
Cu1—N3i	2.032 (4)	C5—H5	0.9300
Cu1—N3	2.032 (4)	C6—C7	1.378 (7)
Cu1—Br2	2.8404 (6)	C6—H6	0.9300
Cu1—Br2i	2.8404 (6)	C7—H7	0.9300
N1—C1	1.383 (6)	C8—C9	1.498 (7)
N1—C4	1.400 (6)	C8—H8A	0.9700
N1—C3	1.412 (6)	C8—H8B	0.9700
N2—C1	1.353 (6)	C9—C10	1.381 (8)
N2—C2	1.396 (6)	C9—C14	1.404 (7)
N2—C8	1.455 (6)	C10—C11	1.362 (8)
N3—C4	1.346 (6)	C11—C12	1.358 (9)
N3—C7	1.348 (6)	C11—H11	0.9300
N4—C4	1.309 (6)	C12—C13	1.384 (9)
N4—C5	1.340 (7)	C12—H12	0.9300
Br1—C10	1.921 (5)	C13—C14	1.384 (9)
O1—C1	1.256 (5)	C13—H13	0.9300
C2—C3	1.314 (7)	C14—H14	0.9300
C2—H2	0.9300
O1i—Cu1—O1	180.00 (11)	N4—C4—N1	115.2 (4)
O1i—Cu1—N3i	88.28 (15)	N3—C4—N1	117.5 (4)
O1—Cu1—N3i	91.72 (15)	N4—C5—C6	122.4 (5)
O1i—Cu1—N3	91.72 (15)	N4—C5—H5	118.8
O1—Cu1—N3	88.28 (15)	C6—C5—H5	118.8
N3i—Cu1—N3	180.000 (1)	C7—C6—C5	116.3 (5)
O1i—Cu1—Br2	92.92 (10)	C7—C6—H6	121.9
O1—Cu1—Br2	87.08 (10)	C5—C6—H6	121.9
N3i—Cu1—Br2	89.16 (11)	N3—C7—C6	122.6 (5)
N3—Cu1—Br2	90.84 (11)	N3—C7—H7	118.7
O1i—Cu1—Br2i	87.08 (10)	C6—C7—H7	118.7
O1—Cu1—Br2i	92.92 (10)	N2—C8—C9	113.2 (4)
N3i—Cu1—Br2i	90.84 (11)	N2—C8—H8A	108.9
N3—Cu1—Br2i	89.16 (11)	C9—C8—H8A	108.9
Br2—Cu1—Br2i	180.00 (2)	N2—C8—H8B	108.9
C1—N1—C4	126.9 (4)	C9—C8—H8B	108.9
C1—N1—C3	108.5 (4)	H8A—C8—H8B	107.8
C4—N1—C3	123.8 (4)	C10—C9—C14	116.3 (5)
C1—N2—C2	108.5 (4)	C10—C9—C8	124.1 (5)
C1—N2—C8	124.7 (4)	C14—C9—C8	119.5 (5)
C2—N2—C8	126.9 (4)	C11—C10—C9	123.4 (5)
C4—N3—C7	115.0 (4)	C11—C10—Br1	116.7 (5)
C4—N3—Cu1	125.5 (3)	C9—C10—Br1	119.9 (4)
C7—N3—Cu1	119.4 (3)	C12—C11—C10	119.4 (6)
C4—N4—C5	116.2 (4)	C12—C11—H11	120.3
C1—O1—Cu1	118.2 (3)	C10—C11—H11	120.3
O1—C1—N2	126.1 (4)	C11—C12—C13	120.3 (6)
O1—C1—N1	127.3 (4)	C11—C12—H12	119.9
N2—C1—N1	106.5 (4)	C13—C12—H12	119.9
C3—C2—N2	109.7 (4)	C12—C13—C14	119.8 (6)
C3—C2—H2	125.1	C12—C13—H13	120.1
N2—C2—H2	125.1	C14—C13—H13	120.1
C2—C3—N1	106.8 (4)	C13—C14—C9	120.8 (6)
C2—C3—H3	126.6	C13—C14—H14	119.6
N1—C3—H3	126.6	C9—C14—H14	119.6
N4—C4—N3	127.3 (5)