Di­bromido­bis­(2-methyl-1H-benzimidazole-κN3)cadmium

Liu, B.-C.; Jin, Y.-L.; Liu, F.-Q.

doi:10.1107/S1600536813024549

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page m536

doi:10.1107/S1600536813024549

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Dibromidobis(2-methyl-1H-benzimidazole-κN³)cadmium

Bao-Cheng Liu,^a ^* Yan-Ling Jin ^a and Fa-Qian Liu ^a

^aKey Laboratory of Advanced Materials, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: qdplastics@163.com

(Received 10 August 2013; accepted 3 September 2013; online 7 September 2013)

In the title compound, [CdBr₂(C₈H₈N₂)₂], the Cd^II atom has a distorted tetrahedral coordination formed by the two imino N atoms of two 2-methylbenzimidazole ligands and two terminal bromide ligands. The Cd^II atom is slightly out of the benzimidazole planes by 0.320 (3) and 0.210 (3) Å. The dihedral angle between the benzimidazole planes is 71.6 (2)°. In the crystal, molecules are linked by N—H⋯Br hydrogen bonds into puckered layers parallel to (001).

Related literature

For background to benzimidazole, see: Roderick et al. (1972 ). For related crystal structures, see: Barros-García et al. (2005 ); Wang et al. (2010 ); Yang et al. (2011 ).

Experimental

Crystal data

[CdBr₂(C₈H₈N₂)₂]
M_r = 536.54
Monoclinic, P 2₁ /c
a = 10.007 (9) Å
b = 14.747 (12) Å
c = 12.399 (11) Å
β = 93.088 (14)°
V = 1827 (3) Å³
Z = 4
Mo Kα radiation
μ = 5.57 mm⁻¹
T = 296 K
0.22 × 0.18 × 0.16 mm

Data collection

Rigaku R-AXIS Spider diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.374, T_max = 0.469
9698 measured reflections
3585 independent reflections
2748 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.077
S = 1.00
3585 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −1.02 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Br1ⁱ	0.86	2.88	3.495 (4)	130
N4—H4⋯Br2ⁱⁱ	0.86	2.77	3.563 (4)	155
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813024549/kq2008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813024549/kq2008Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813024549/kq2008Isup3.cdx

checkCIF report

Comment top

Benzimidazole and its derivatives have attracted interest because their biological activities as well as their abilities to bind different metal ions (Roderick et al., 1972). In this paper, we describe the synthesis and structure of dibromo-bis(2-methylbenzimidazole)-cadmium(II).

In the title compound, C₁₆H₁₆CdBr₂N₄, the cadmium atom has a distorted tetrahedral coordination formed by the two imino-nitrogen atoms of two 2-methyl-benzimidazole ligands and two terminal bromide ligands (Figure 1). The similar geometry was previously found in the related compounds – Cd(Cl)₂(N-(5,6-dihydro-4H- 1,3-thiazin-2-yl)-2-aminobenzimidazole)₂ (Barros-García et al., 2005), Cd(Cl)₂(2-(2-furyl)-1-(2-furylmethyl)-1H-benzimidazole)₂ (Wang et al., 2010), and Cd(I)₂(2-(2-furyl)-1-(2-furylmethyl)- 1H-enzimidazole)₂ (Yang et al., 2011). The cadmium atom is slightly out of the two benzimidazole planes by 0.320 (3) and 0.210 (3) Å, respectively. The dihedral angle between the two benzimidazole planes is 71.6 (2)°. The mean values of Cd—Br and Cd—N bond lengths are 2.562 (2) and 2.251 (3) Å, respectively. The N—Cd—Br bond angles range from 105.40 (10) to 117.76 (9)°.

In the crystal, the molecules of the title compound are linked by intermolecular N2—H2···Br1ⁱ and N4—H4···Br2ⁱⁱ hydrogen bonds (Table 1) into puckered layers parallel to (001) (Figure 2). Symmetry codes: (i) –x+1, y–1/2, –z+3/2; (ii) –x, y–1/2, –z+3/2.

Related literature top

For background to benzimidazole, see: Roderick et al. (1972). For related crystal structures, see: Barros-García et al. (2005); Wang et al. (2010); Yang et al. (2011).

Experimental top

The ligand 2-methyl-benzimidazole (0.02 mmol) in ethanol (10 mL) was added dropwise to a ethanol (10 mL) of CdBr₂(0.01 mmol). The resulting solution was allowed to stand at room temperature. After one week colorless crystals with good quality were obtained from the filtrate and dried in air. Analysis, calculated for C₁₆H₁₆Br₂CdN₄: C 35.82, H 3.01, N 10.44%; Found: C 35.68, H 3.02, N 10.47%.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are shown at the 40% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. Crystal packing of the title compound along the b axis demonstrating the puckered layers parallel to (001). Dashed lines indicate the intermolecular hydrogen bonds.

Dibromidobis(2-methyl-1H-benzimidazole-κN³)cadmium top

Crystal data top

[CdBr₂(C₈H₈N₂)₂]	F(000) = 1032
M_r = 536.54	D_x = 1.951 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3275 reflections
a = 10.007 (9) Å	θ = 2.5–26.6°
b = 14.747 (12) Å	µ = 5.57 mm⁻¹
c = 12.399 (11) Å	T = 296 K
β = 93.088 (14)°	Block, colorless
V = 1827 (3) Å³	0.22 × 0.18 × 0.16 mm
Z = 4

Data collection top

Rigaku R-AXIS Spider diffractometer	2748 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 26.0°, θ_min = 2.0°
ω scans	h = −12→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −18→14
T_min = 0.374, T_max = 0.469	l = −15→14
9698 measured reflections	13 standard reflections every 0 reflections
3585 independent reflections	intensity decay: none

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0407P)²] where P = (F_o² + 2F_c²)/3
3585 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −1.02 e Å⁻³

Crystal data top

[CdBr₂(C₈H₈N₂)₂]	V = 1827 (3) Å³
M_r = 536.54	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.007 (9) Å	µ = 5.57 mm⁻¹
b = 14.747 (12) Å	T = 296 K
c = 12.399 (11) Å	0.22 × 0.18 × 0.16 mm
β = 93.088 (14)°

Data collection top

Rigaku R-AXIS Spider diffractometer	2748 reflections with I > 2σ(I)
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	R_int = 0.032
T_min = 0.374, T_max = 0.469	13 standard reflections every 0 reflections
9698 measured reflections	intensity decay: none
3585 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.00	Δρ_max = 0.39 e Å⁻³
3585 reflections	Δρ_min = −1.02 e Å⁻³
210 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
N1	0.3592 (3)	0.96335 (19)	0.8577 (2)	0.0362 (7)
N2	0.5028 (4)	0.8661 (2)	0.9341 (3)	0.0485 (9)
H2	0.5712	0.8311	0.9428	0.058*
N3	0.0723 (3)	1.01679 (18)	0.6820 (2)	0.0339 (7)
N4	−0.1049 (3)	0.93220 (19)	0.6357 (2)	0.0417 (8)
H4	−0.1554	0.8851	0.6290	0.050*
Br1	0.40130 (5)	1.14156 (3)	0.60773 (4)	0.06071 (16)
Br2	0.20546 (5)	1.20099 (3)	0.88850 (4)	0.06367 (17)
C1	0.4087 (4)	0.8806 (2)	1.0086 (3)	0.0409 (9)
C2	0.3939 (5)	0.8457 (3)	1.1109 (3)	0.0531 (12)
H2A	0.4561	0.8060	1.1434	0.064*
C3	0.2816 (6)	0.8730 (3)	1.1622 (4)	0.0626 (14)
H3	0.2681	0.8511	1.2311	0.075*
C4	0.1873 (6)	0.9326 (3)	1.1139 (4)	0.0633 (13)
H4A	0.1119	0.9482	1.1505	0.076*
C5	0.2045 (5)	0.9687 (3)	1.0127 (3)	0.0535 (11)
H5	0.1432	1.0094	0.9812	0.064*
C6	0.3175 (4)	0.9417 (2)	0.9597 (3)	0.0368 (9)
C7	0.4708 (4)	0.9156 (2)	0.8454 (3)	0.0408 (9)
C8	0.5489 (5)	0.9139 (3)	0.7478 (4)	0.0620 (13)
H8A	0.4935	0.9338	0.6867	0.093*
H8B	0.5793	0.8532	0.7355	0.093*
H8C	0.6246	0.9536	0.7578	0.093*
C9	−0.0236 (4)	1.0707 (2)	0.6250 (3)	0.0332 (8)
C10	−0.0180 (4)	1.1618 (2)	0.5961 (3)	0.0420 (9)
H10	0.0571	1.1972	0.6131	0.050*
C11	−0.1303 (5)	1.1972 (3)	0.5406 (3)	0.0502 (11)
H11	−0.1297	1.2575	0.5187	0.060*
C12	−0.2441 (5)	1.1449 (3)	0.5168 (3)	0.0531 (11)
H12	−0.3184	1.1720	0.4820	0.064*
C13	−0.2499 (4)	1.0548 (3)	0.5431 (3)	0.0482 (10)
H13	−0.3255	1.0199	0.5259	0.058*
C14	−0.1372 (4)	1.0184 (2)	0.5966 (3)	0.0364 (9)
C15	0.0180 (4)	0.9343 (2)	0.6856 (3)	0.0386 (9)
C16	0.0818 (5)	0.8531 (2)	0.7384 (3)	0.0577 (13)
H16A	0.1749	0.8514	0.7233	0.087*
H16B	0.0384	0.7992	0.7108	0.087*
H16C	0.0733	0.8566	0.8150	0.087*
Cd1	0.26490 (3)	1.074421 (18)	0.75481 (2)	0.03930 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.039 (2)	0.0255 (15)	0.0436 (18)	0.0043 (14)	0.0033 (15)	0.0002 (14)
N2	0.044 (2)	0.0340 (18)	0.066 (2)	0.0133 (15)	−0.0060 (18)	0.0078 (17)
N3	0.0365 (18)	0.0242 (15)	0.0410 (16)	−0.0068 (13)	0.0015 (14)	−0.0021 (13)
N4	0.048 (2)	0.0289 (17)	0.0482 (19)	−0.0128 (14)	0.0016 (16)	−0.0055 (14)
Br1	0.0653 (3)	0.0460 (3)	0.0713 (3)	−0.0150 (2)	0.0077 (2)	0.0149 (2)
Br2	0.0746 (4)	0.0398 (3)	0.0745 (3)	0.0205 (2)	−0.0163 (3)	−0.0179 (2)
C1	0.044 (2)	0.027 (2)	0.050 (2)	−0.0007 (17)	−0.010 (2)	0.0000 (18)
C2	0.066 (3)	0.039 (2)	0.053 (3)	−0.008 (2)	−0.017 (2)	0.006 (2)
C3	0.089 (4)	0.058 (3)	0.041 (2)	−0.018 (3)	0.003 (3)	−0.003 (2)
C4	0.082 (4)	0.057 (3)	0.052 (3)	0.005 (3)	0.016 (3)	−0.005 (2)
C5	0.058 (3)	0.049 (3)	0.053 (3)	0.016 (2)	0.002 (2)	−0.003 (2)
C6	0.043 (2)	0.0256 (19)	0.041 (2)	−0.0001 (16)	0.0017 (18)	−0.0006 (16)
C7	0.039 (2)	0.030 (2)	0.053 (2)	0.0008 (17)	0.0057 (19)	−0.0037 (18)
C8	0.057 (3)	0.050 (3)	0.081 (3)	0.006 (2)	0.027 (3)	−0.005 (2)
C9	0.037 (2)	0.030 (2)	0.0328 (19)	0.0039 (16)	0.0046 (16)	−0.0025 (16)
C10	0.046 (3)	0.033 (2)	0.048 (2)	−0.0044 (18)	0.0004 (19)	−0.0034 (18)
C11	0.068 (3)	0.029 (2)	0.053 (2)	0.013 (2)	−0.003 (2)	−0.0004 (19)
C12	0.051 (3)	0.054 (3)	0.053 (3)	0.013 (2)	−0.010 (2)	−0.006 (2)
C13	0.041 (3)	0.053 (3)	0.050 (2)	−0.004 (2)	−0.005 (2)	−0.011 (2)
C14	0.041 (2)	0.035 (2)	0.0341 (19)	−0.0006 (17)	0.0046 (17)	−0.0080 (16)
C15	0.051 (3)	0.028 (2)	0.038 (2)	−0.0037 (17)	0.0054 (19)	0.0007 (16)
C16	0.082 (4)	0.030 (2)	0.059 (3)	−0.008 (2)	−0.014 (2)	0.011 (2)
Cd1	0.04113 (19)	0.02686 (16)	0.04918 (18)	0.00061 (12)	−0.00430 (13)	0.00266 (12)

Geometric parameters (Å, º) top

N1—C7	1.336 (5)	C4—H4A	0.9300
N1—C6	1.390 (5)	C5—C6	1.396 (6)
N1—Cd1	2.252 (3)	C5—H5	0.9300
N2—C7	1.345 (5)	C7—C8	1.475 (6)
N2—C1	1.370 (5)	C8—H8A	0.9600
N2—H2	0.8600	C8—H8B	0.9600
N3—C15	1.334 (4)	C8—H8C	0.9600
N3—C9	1.407 (5)	C9—C10	1.393 (5)
N3—Cd1	2.250 (3)	C9—C14	1.403 (5)
N4—C15	1.347 (5)	C10—C11	1.387 (6)
N4—C14	1.392 (5)	C10—H10	0.9300
N4—H4	0.8600	C11—C12	1.394 (6)
Br1—Cd1	2.5372 (15)	C11—H11	0.9300
Br2—Cd1	2.5869 (15)	C12—C13	1.370 (6)
C1—C2	1.385 (6)	C12—H12	0.9300
C1—C6	1.398 (5)	C13—C14	1.386 (6)
C2—C3	1.381 (7)	C13—H13	0.9300
C2—H2A	0.9300	C15—C16	1.492 (5)
C3—C4	1.401 (7)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.381 (6)	C16—H16C	0.9600

C7—N1—C6	106.1 (3)	C7—C8—H8C	109.5
C7—N1—Cd1	130.2 (3)	H8A—C8—H8C	109.5
C6—N1—Cd1	123.1 (2)	H8B—C8—H8C	109.5
C7—N2—C1	109.0 (3)	C10—C9—C14	120.6 (4)
C7—N2—H2	125.5	C10—C9—N3	129.7 (4)
C1—N2—H2	125.5	C14—C9—N3	109.7 (3)
C15—N3—C9	105.3 (3)	C11—C10—C9	116.6 (4)
C15—N3—Cd1	132.3 (3)	C11—C10—H10	121.7
C9—N3—Cd1	122.3 (2)	C9—C10—H10	121.7
C15—N4—C14	109.1 (3)	C10—C11—C12	121.9 (4)
C15—N4—H4	125.4	C10—C11—H11	119.1
C14—N4—H4	125.4	C12—C11—H11	119.1
N2—C1—C2	132.2 (4)	C13—C12—C11	122.1 (4)
N2—C1—C6	105.3 (3)	C13—C12—H12	119.0
C2—C1—C6	122.5 (4)	C11—C12—H12	119.0
C3—C2—C1	116.3 (4)	C12—C13—C14	116.5 (4)
C3—C2—H2A	121.8	C12—C13—H13	121.8
C1—C2—H2A	121.8	C14—C13—H13	121.8
C2—C3—C4	122.2 (4)	C13—C14—N4	133.4 (4)
C2—C3—H3	118.9	C13—C14—C9	122.3 (4)
C4—C3—H3	118.9	N4—C14—C9	104.2 (3)
C5—C4—C3	121.0 (5)	N3—C15—N4	111.7 (3)
C5—C4—H4A	119.5	N3—C15—C16	125.5 (4)
C3—C4—H4A	119.5	N4—C15—C16	122.8 (3)
C4—C5—C6	117.5 (4)	C15—C16—H16A	109.5
C4—C5—H5	121.2	C15—C16—H16B	109.5
C6—C5—H5	121.2	H16A—C16—H16B	109.5
N1—C6—C5	130.8 (4)	C15—C16—H16C	109.5
N1—C6—C1	108.8 (3)	H16A—C16—H16C	109.5
C5—C6—C1	120.4 (4)	H16B—C16—H16C	109.5
N1—C7—N2	110.8 (3)	N3—Cd1—N1	106.04 (12)
N1—C7—C8	125.9 (4)	N3—Cd1—Br1	109.95 (9)
N2—C7—C8	123.3 (4)	N1—Cd1—Br1	117.77 (9)
C7—C8—H8A	109.5	N3—Cd1—Br2	107.95 (9)
C7—C8—H8B	109.5	N1—Cd1—Br2	105.40 (9)
H8A—C8—H8B	109.5	Br1—Cd1—Br2	109.28 (2)

C7—N2—C1—C2	178.9 (4)	C9—C10—C11—C12	1.2 (6)
C7—N2—C1—C6	0.1 (4)	C10—C11—C12—C13	−2.5 (7)
N2—C1—C2—C3	−177.2 (4)	C11—C12—C13—C14	1.1 (6)
C6—C1—C2—C3	1.3 (6)	C12—C13—C14—N4	−179.9 (4)
C1—C2—C3—C4	0.1 (7)	C12—C13—C14—C9	1.4 (6)
C2—C3—C4—C5	−1.5 (7)	C15—N4—C14—C13	−177.7 (4)
C3—C4—C5—C6	1.5 (7)	C15—N4—C14—C9	1.2 (4)
C7—N1—C6—C5	−177.1 (4)	C10—C9—C14—C13	−2.7 (6)
Cd1—N1—C6—C5	11.3 (6)	N3—C9—C14—C13	177.7 (3)
C7—N1—C6—C1	0.9 (4)	C10—C9—C14—N4	178.3 (3)
Cd1—N1—C6—C1	−170.7 (2)	N3—C9—C14—N4	−1.4 (4)
C4—C5—C6—N1	177.6 (4)	C9—N3—C15—N4	−0.2 (4)
C4—C5—C6—C1	−0.2 (6)	Cd1—N3—C15—N4	175.6 (2)
N2—C1—C6—N1	−0.6 (4)	C9—N3—C15—C16	−179.7 (4)
C2—C1—C6—N1	−179.5 (3)	Cd1—N3—C15—C16	−3.9 (6)
N2—C1—C6—C5	177.6 (4)	C14—N4—C15—N3	−0.6 (4)
C2—C1—C6—C5	−1.3 (6)	C14—N4—C15—C16	178.9 (4)
C6—N1—C7—N2	−0.9 (4)	C15—N3—Cd1—N1	−4.6 (3)
Cd1—N1—C7—N2	169.9 (2)	C9—N3—Cd1—N1	170.6 (2)
C6—N1—C7—C8	177.7 (4)	C15—N3—Cd1—Br1	123.7 (3)
Cd1—N1—C7—C8	−11.5 (6)	C9—N3—Cd1—Br1	−61.0 (3)
C1—N2—C7—N1	0.5 (4)	C15—N3—Cd1—Br2	−117.1 (3)
C1—N2—C7—C8	−178.1 (4)	C9—N3—Cd1—Br2	58.1 (3)
C15—N3—C9—C10	−178.6 (4)	C7—N1—Cd1—N3	112.4 (3)
Cd1—N3—C9—C10	5.1 (5)	C6—N1—Cd1—N3	−78.2 (3)
C15—N3—C9—C14	1.0 (4)	C7—N1—Cd1—Br1	−11.1 (4)
Cd1—N3—C9—C14	−175.3 (2)	C6—N1—Cd1—Br1	158.3 (2)
C14—C9—C10—C11	1.3 (5)	C7—N1—Cd1—Br2	−133.3 (3)
N3—C9—C10—C11	−179.1 (3)	C6—N1—Cd1—Br2	36.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Br1ⁱ	0.86	2.88	3.495 (4)	130
N4—H4···Br2ⁱⁱ	0.86	2.77	3.563 (4)	155

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Br1ⁱ	0.86	2.88	3.495 (4)	130
N4—H4···Br2ⁱⁱ	0.86	2.77	3.563 (4)	155

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

Acknowledgements

This work was supported by the NSF of Shandong Province (No. 2009ZRA02071), the Scientific Development Plan of Universities in Shandong Province (No. J09LB53) and the Doctoral Science Foundation of QUST.

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