{N-[1-(1H-Benzimidazol-2-yl)ethyl-idene-κN]-3-(1H-imidazol-1-yl)propan-1-amine-κN}dibromidomercury(II).

In the title compound, [HgBr(2)(C(15)H(17)N(5))], the Hg(II) ion is tetra-hedrally coordinated by two N atoms of the N-[1-(1H-benzimidazol-2-yl)ethyl-idene-κN]-3-(1H-imidazol-1-yl)propan-1-amine ligand, and two bromide anions. Inter-molecular benzimidazole-imidazole N-H⋯N hydrogen bonds link the mol-ecules into helical chains along the b-axis direction and C-H⋯Br hydrogen bonds link these chains into layers parallel to the bc plane.

Related literature

For general background to the design and synthesis of coordination pan class="Chemical">polymers, see: Moulton & Zaworotko (2001 ▶); Roesky & Andruh (2003 ▶); Li et al. (2007 ▶); Zheng et al. (2011 ▶). For complexes with ligands containing pan class="Chemical">benzimidazole or pan class="Chemical">imidazole, see: Pan et al. (2010 ▶); Chen et al. (2007 ▶); Zhuang et al. (2009 ▶); Wang et al. (2009 ▶).

Experimental

Crystal data

[HgBr2(C15H17N5)]

M = 627.75

Monoclinic,

a = 10.3054 (4) Å

b = 10.6680 (4) Å

c = 16.6030 (5) Å

β = 100.844 (3)°

V = 1792.71 (11) Å3

Z = 4

Mo Kα radiation

μ = 13.05 mm−1

T = 298 K

0.37 × 0.33 × 0.30 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.086, T max = 0.111

9489 measured reflections

3891 independent reflections

2302 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.041

S = 0.93

3891 reflections

208 parameters

H-atom parameters constrained

Δρmax = 1.45 e Å−3

Δρmin = −0.96 e Å−3

Data collection: pan class="Gene">APEX2n> (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051166/kp2360sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051166/kp2360Isup2.hkl

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

[HgBr2(C15H17N5)]	Z = 4
Mr = 627.75	F(000) = 1168
Monoclinic, P21/c	Dx = 2.326 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.3054 (4) Å	θ = 2.8–27°
b = 10.6680 (4) Å	µ = 13.05 mm−1
c = 16.6030 (5) Å	T = 298 K
β = 100.844 (3)°	Block, colourless
V = 1792.71 (11) Å3	0.37 × 0.33 × 0.30 mm

Bruker SMART APEXII CCD area-detector diffractometer	3891 independent reflections
Radiation source: fine-focus sealed tube	2302 reflections with I > 2σ(I)
graphite	Rint = 0.047
phi and ω scans	θmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.086, Tmax = 0.111	k = −13→12
9489 measured reflections	l = −21→20

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.041	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.P)2] where P = (Fo2 + 2Fc2)/3
3891 reflections	(Δ/σ)max = 0.003
208 parameters	Δρmax = 1.45 e Å−3
0 restraints	Δρmin = −0.96 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
Hg1	0.28943 (2)	1.69192 (2)	1.065782 (13)	0.02437 (7)
Br2	0.09981 (6)	1.80104 (7)	1.10987 (3)	0.03381 (17)
Br1	0.34657 (6)	1.46862 (6)	1.11412 (3)	0.03254 (18)
N3	0.2664 (4)	1.6902 (5)	0.9191 (2)	0.0196 (11)
N1	0.4643 (4)	1.7966 (4)	1.0326 (2)	0.0153 (11)
C7	0.4677 (5)	1.7955 (6)	0.9526 (3)	0.0220 (14)
C1	0.5760 (5)	1.8564 (5)	1.0723 (3)	0.0164 (14)
C6	0.6472 (6)	1.8935 (5)	1.0109 (3)	0.0179 (14)
C9	0.3613 (6)	1.7408 (5)	0.8910 (3)	0.0176 (14)
C10	0.1465 (5)	1.6394 (5)	0.8673 (3)	0.0242 (16)
H10A	0.1617	1.6287	0.8118	0.029*
H10B	0.0746	1.6986	0.8656	0.029*
N4	0.2183 (5)	1.3873 (4)	0.8074 (3)	0.0210 (12)
N2	0.5751 (4)	1.8553 (4)	0.9374 (3)	0.0204 (12)
H2B	0.5949	1.8674	0.8900	0.025*
N5	0.3055 (5)	1.3730 (4)	0.6951 (3)	0.0264 (13)
C2	0.6247 (6)	1.8854 (5)	1.1536 (3)	0.0242 (16)
H2A	0.5776	1.8646	1.1943	0.029*
C5	0.7670 (6)	1.9576 (6)	1.0293 (3)	0.0259 (16)
H5A	0.8123	1.9828	0.9886	0.031*
C8	0.3749 (5)	1.7525 (5)	0.8032 (3)	0.0225 (15)
H8A	0.3003	1.7140	0.7687	0.034*
H8B	0.4545	1.7114	0.7953	0.034*
H8C	0.3788	1.8395	0.7891	0.034*
C4	0.8144 (6)	1.9815 (5)	1.1109 (4)	0.0318 (18)
H4A	0.8950	2.0223	1.1260	0.038*
C15	0.3258 (6)	1.4068 (5)	0.7735 (3)	0.0252 (16)
H15A	0.4049	1.4400	0.8017	0.030*
C14	0.1767 (6)	1.3299 (5)	0.6795 (3)	0.0250 (16)
H14A	0.1328	1.2997	0.6292	0.030*
C3	0.7431 (6)	1.9453 (6)	1.1726 (3)	0.0295 (17)
H3A	0.7782	1.9630	1.2272	0.035*
C13	0.1234 (6)	1.3376 (5)	0.7478 (3)	0.0272 (17)
H13A	0.0386	1.3138	0.7531	0.033*
C11	0.1081 (5)	1.5158 (5)	0.8992 (3)	0.0198 (14)
H11A	0.0221	1.4915	0.8686	0.024*
H11B	0.1007	1.5253	0.9562	0.024*
C12	0.2065 (6)	1.4126 (5)	0.8924 (3)	0.0268 (16)
H12A	0.2923	1.4364	0.9234	0.032*
H12B	0.1791	1.3366	0.9165	0.032*

	U11	U22	U33	U12	U13	U23
Hg1	0.02425 (14)	0.03019 (14)	0.01982 (12)	0.00036 (16)	0.00710 (9)	0.00116 (13)
Br2	0.0283 (4)	0.0368 (4)	0.0408 (4)	0.0044 (4)	0.0179 (3)	0.0032 (4)
Br1	0.0381 (5)	0.0283 (4)	0.0284 (4)	0.0013 (3)	−0.0008 (3)	0.0050 (3)
N3	0.026 (3)	0.020 (3)	0.014 (2)	0.001 (3)	0.006 (2)	−0.002 (2)
N1	0.019 (3)	0.015 (3)	0.014 (2)	0.003 (3)	0.008 (2)	0.000 (2)
C7	0.021 (4)	0.028 (4)	0.017 (3)	0.004 (3)	0.002 (3)	0.004 (3)
C1	0.013 (4)	0.011 (3)	0.023 (3)	0.003 (3)	−0.003 (3)	0.006 (3)
C6	0.016 (4)	0.013 (4)	0.025 (4)	0.000 (3)	0.005 (3)	0.001 (3)
C9	0.018 (4)	0.016 (3)	0.018 (3)	0.014 (3)	0.002 (3)	0.002 (3)
C10	0.026 (4)	0.035 (4)	0.011 (3)	0.008 (3)	0.001 (3)	0.003 (3)
N4	0.016 (3)	0.026 (3)	0.022 (3)	−0.005 (3)	0.008 (2)	0.000 (2)
N2	0.016 (3)	0.027 (3)	0.021 (3)	0.001 (2)	0.012 (2)	0.004 (2)
N5	0.029 (4)	0.030 (3)	0.021 (3)	−0.003 (3)	0.008 (3)	−0.001 (2)
C2	0.027 (4)	0.026 (4)	0.021 (4)	0.004 (3)	0.006 (3)	−0.005 (3)
C5	0.028 (4)	0.029 (4)	0.022 (3)	0.010 (3)	0.010 (3)	0.004 (3)
C8	0.024 (4)	0.027 (4)	0.017 (3)	0.000 (3)	0.004 (3)	−0.003 (3)
C4	0.020 (4)	0.017 (4)	0.055 (5)	−0.004 (3)	−0.002 (4)	0.006 (3)
C15	0.016 (4)	0.028 (4)	0.027 (4)	−0.002 (3)	−0.006 (3)	−0.004 (3)
C14	0.025 (4)	0.033 (4)	0.016 (3)	−0.008 (3)	0.001 (3)	−0.009 (3)
C3	0.039 (5)	0.027 (4)	0.021 (4)	0.009 (4)	0.002 (3)	0.000 (3)
C13	0.018 (4)	0.041 (5)	0.023 (3)	−0.003 (3)	0.003 (3)	−0.005 (3)
C11	0.017 (4)	0.023 (4)	0.022 (3)	−0.003 (3)	0.009 (3)	−0.007 (3)
C12	0.034 (4)	0.032 (4)	0.014 (3)	−0.007 (3)	0.004 (3)	−0.004 (3)

Hg1—N1	2.274 (4)	N5—C15	1.329 (6)
Hg1—N3	2.403 (4)	N5—C14	1.382 (6)
Hg1—Br2	2.4996 (7)	C2—C3	1.361 (7)
Hg1—Br1	2.5472 (7)	C2—H2A	0.9300
N3—C9	1.280 (6)	C5—C4	1.374 (7)
N3—C10	1.469 (6)	C5—H5A	0.9300
N1—C7	1.335 (5)	C8—H8A	0.9600
N1—C1	1.372 (6)	C8—H8B	0.9600
C7—N2	1.342 (6)	C8—H8C	0.9600
C7—C9	1.472 (7)	C4—C3	1.422 (7)
C1—C2	1.384 (6)	C4—H4A	0.9300
C1—C6	1.420 (7)	C15—H15A	0.9300
C6—N2	1.366 (6)	C14—C13	1.352 (6)
C6—C5	1.393 (7)	C14—H14A	0.9300
C9—C8	1.497 (6)	C3—H3A	0.9300
C10—C11	1.502 (7)	C13—H13A	0.9300
C10—H10A	0.9700	C11—C12	1.514 (7)
C10—H10B	0.9700	C11—H11A	0.9700
N4—C15	1.350 (6)	C11—H11B	0.9700
N4—C13	1.360 (6)	C12—H12A	0.9700
N4—C12	1.465 (6)	C12—H12B	0.9700
N2—H2B	0.8600
N1—Hg1—N3	71.94 (15)	C3—C2—H2A	120.8
N1—Hg1—Br2	122.76 (11)	C1—C2—H2A	120.8
N3—Hg1—Br2	111.53 (11)	C4—C5—C6	116.3 (5)
N1—Hg1—Br1	112.88 (11)	C4—C5—H5A	121.8
N3—Hg1—Br1	106.56 (12)	C6—C5—H5A	121.8
Br2—Hg1—Br1	119.37 (2)	C9—C8—H8A	109.5
C9—N3—C10	124.0 (5)	C9—C8—H8B	109.5
C9—N3—Hg1	115.4 (4)	H8A—C8—H8B	109.5
C10—N3—Hg1	120.5 (3)	C9—C8—H8C	109.5
C7—N1—C1	107.8 (5)	H8A—C8—H8C	109.5
C7—N1—Hg1	114.0 (4)	H8B—C8—H8C	109.5
C1—N1—Hg1	138.0 (3)	C5—C4—C3	121.6 (6)
N1—C7—N2	111.1 (5)	C5—C4—H4A	119.2
N1—C7—C9	122.6 (5)	C3—C4—H4A	119.2
N2—C7—C9	126.2 (5)	N5—C15—N4	112.1 (5)
N1—C1—C2	133.6 (5)	N5—C15—H15A	124.0
N1—C1—C6	106.6 (5)	N4—C15—H15A	124.0
C2—C1—C6	119.8 (5)	C13—C14—N5	110.5 (5)
N2—C6—C5	130.8 (5)	C13—C14—H14A	124.8
N2—C6—C1	106.9 (5)	N5—C14—H14A	124.8
C5—C6—C1	122.4 (5)	C2—C3—C4	121.5 (5)
N3—C9—C7	115.8 (5)	C2—C3—H3A	119.2
N3—C9—C8	127.4 (5)	C4—C3—H3A	119.2
C7—C9—C8	116.8 (5)	C14—C13—N4	106.5 (5)
N3—C10—C11	111.5 (4)	C14—C13—H13A	126.8
N3—C10—H10A	109.3	N4—C13—H13A	126.8
C11—C10—H10A	109.3	C10—C11—C12	112.8 (4)
N3—C10—H10B	109.3	C10—C11—H11A	109.0
C11—C10—H10B	109.3	C12—C11—H11A	109.0
H10A—C10—H10B	108.0	C10—C11—H11B	109.0
C15—N4—C13	107.0 (5)	C12—C11—H11B	109.0
C15—N4—C12	126.6 (5)	H11A—C11—H11B	107.8
C13—N4—C12	126.4 (5)	N4—C12—C11	112.6 (4)
C7—N2—C6	107.7 (4)	N4—C12—H12A	109.1
C7—N2—H2B	126.2	C11—C12—H12A	109.1
C6—N2—H2B	126.2	N4—C12—H12B	109.1
C15—N5—C14	104.0 (5)	C11—C12—H12B	109.1
C3—C2—C1	118.4 (5)	H12A—C12—H12B	107.8
N1—Hg1—N3—C9	3.1 (4)	N1—C7—C9—N3	−2.2 (8)
Br2—Hg1—N3—C9	122.0 (4)	N2—C7—C9—N3	−178.6 (5)
Br1—Hg1—N3—C9	−106.1 (4)	N1—C7—C9—C8	176.8 (5)
N1—Hg1—N3—C10	−173.8 (4)	N2—C7—C9—C8	0.4 (8)
Br2—Hg1—N3—C10	−54.9 (4)	C9—N3—C10—C11	137.0 (5)
Br1—Hg1—N3—C10	77.0 (4)	Hg1—N3—C10—C11	−46.3 (5)
N3—Hg1—N1—C7	−4.0 (4)	N1—C7—N2—C6	2.1 (6)
Br2—Hg1—N1—C7	−108.5 (4)	C9—C7—N2—C6	178.8 (5)
Br1—Hg1—N1—C7	96.8 (4)	C5—C6—N2—C7	179.1 (6)
N3—Hg1—N1—C1	−178.7 (6)	C1—C6—N2—C7	−1.4 (6)
Br2—Hg1—N1—C1	76.9 (5)	N1—C1—C2—C3	178.9 (6)
Br1—Hg1—N1—C1	−77.9 (5)	C6—C1—C2—C3	−2.4 (8)
C1—N1—C7—N2	−1.8 (6)	N2—C6—C5—C4	−179.6 (5)
Hg1—N1—C7—N2	−178.1 (4)	C1—C6—C5—C4	1.0 (8)
C1—N1—C7—C9	−178.7 (5)	C6—C5—C4—C3	−1.5 (8)
Hg1—N1—C7—C9	5.1 (7)	C14—N5—C15—N4	0.1 (6)
C7—N1—C1—C2	179.6 (6)	C13—N4—C15—N5	0.3 (7)
Hg1—N1—C1—C2	−5.5 (10)	C12—N4—C15—N5	179.3 (5)
C7—N1—C1—C6	0.8 (6)	C15—N5—C14—C13	−0.4 (6)
Hg1—N1—C1—C6	175.7 (4)	C1—C2—C3—C4	2.0 (9)
N1—C1—C6—N2	0.4 (6)	C5—C4—C3—C2	0.0 (9)
C2—C1—C6—N2	−178.6 (5)	N5—C14—C13—N4	0.6 (6)
N1—C1—C6—C5	179.9 (5)	C15—N4—C13—C14	−0.5 (6)
C2—C1—C6—C5	0.9 (8)	C12—N4—C13—C14	−179.6 (5)
C10—N3—C9—C7	175.0 (5)	N3—C10—C11—C12	−67.2 (6)
Hg1—N3—C9—C7	−1.7 (6)	C15—N4—C12—C11	114.2 (6)
C10—N3—C9—C8	−3.8 (9)	C13—N4—C12—C11	−67.0 (7)
Hg1—N3—C9—C8	179.4 (4)	C10—C11—C12—N4	−61.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N5i	0.86	1.90	2.722 (7)	160
C15—H15A···Br1ii	0.93	2.85	3.778 (6)	177.

Table 1

Selected bond lengths (Å)

Hg1—N1	2.274 (4)
Hg1—N3	2.403 (4)
Hg1—Br2	2.4996 (7)
Hg1—Br1	2.5472 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N5i	0.86	1.90	2.722 (7)	160
C15—H15A⋯Br1ii	0.93	2.85	3.778 (6)	177

Symmetry codes: (i) ; (ii) .