Bis[2-(2-amino-ethyl)-1H-benzimidazole-κN,N]zinc(II) bis-(perchlorate).

In the title compound, [Zn(C(9)H(11)N(3))(2)](ClO(4))(2), the Zn(II) atom resides on a crystallographic twofold axis and is coordinated by two benzimidazole N [Zn⋯N = 1.993 (4) Å] and two amine N atoms [Zn⋯N = 2.036 (4) Å] in a distorted tetra-hedral geometry. The crystal packing is dominated by N-H⋯O inter-actions involving the perchlorate anions and π-π stacking inter-actions with an inter-planar separation of 3.42 Å. A weak C-H⋯O inter-action is also present.

Related literature

For related literature, see: Cescon & Day (1961 ▶); Maurva et al. (2006 ▶); Qiu & Tong (2005 ▶); Vallee & Auld (1990 ▶).

Experimental

Crystal data

[Zn(C9H11N3)2](ClO4)2

M = 586.69

Monoclinic,

a = 11.150 (3) Å

b = 15.343 (4) Å

c = 14.156 (4) Å

β = 93.322 (4)°

V = 2417.7 (12) Å3

Z = 4

Mo Kα radiation

μ = 1.29 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.698, T max = 0.782

5777 measured reflections

2131 independent reflections

1880 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.184

S = 1.10

2131 reflections

172 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2000 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706610X/gg2058sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706610X/gg2058Isup2.hkl

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

[Zn(C9H11N3)2](ClO4)2	F000 = 1200
Mr = 586.69	Dx = 1.612 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1957 reflections
a = 11.150 (3) Å	θ = 2.3–23.9º
b = 15.343 (4) Å	µ = 1.29 mm−1
c = 14.156 (4) Å	T = 293 (2) K
β = 93.322 (4)º	Block, colorless
V = 2417.7 (12) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2131 independent reflections
Radiation source: fine-focus sealed tube	1880 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
T = 293(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.698, Tmax = 0.782	k = −18→18
5777 measured reflections	l = −10→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066	H-atom parameters constrained
wR(F2) = 0.184	w = 1/[σ2(Fo2) + (0.1191P)2 + 1.6906P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2131 reflections	Δρmax = 0.81 e Å−3
172 parameters	Δρmin = −0.47 e Å−3
15 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
Zn1	1.0000	0.13946 (4)	0.2500	0.0506 (3)
N1	0.8741 (3)	0.2124 (2)	0.1829 (3)	0.0534 (9)
N2	0.6929 (3)	0.2674 (3)	0.1500 (3)	0.0655 (11)
H2A	0.6165	0.2745	0.1504	0.079*
C1	0.8843 (4)	0.2811 (3)	0.1191 (3)	0.0538 (11)
C2	0.9833 (5)	0.3136 (4)	0.0754 (4)	0.0712 (14)
H2	1.0595	0.2900	0.0872	0.085*
C3	0.9638 (6)	0.3819 (4)	0.0142 (5)	0.0805 (16)
H3	1.0287	0.4055	−0.0155	0.097*
C4	0.8497 (6)	0.4174 (4)	−0.0050 (4)	0.0776 (16)
H4	0.8413	0.4643	−0.0464	0.093*
C5	0.7494 (6)	0.3855 (3)	0.0351 (4)	0.0686 (14)
H5	0.6732	0.4083	0.0211	0.082*
C6	0.7700 (4)	0.3157 (3)	0.0990 (3)	0.0549 (11)
C7	0.7577 (4)	0.2068 (3)	0.1993 (4)	0.0624 (12)
C8	0.7035 (6)	0.1424 (4)	0.2624 (5)	0.0905 (17)
H8A	0.6298	0.1675	0.2837	0.109*	0.594 (12)
H8B	0.6812	0.0916	0.2247	0.109*	0.594 (12)
H8A'	0.6876	0.1728	0.3205	0.109*	0.406 (12)
H8B'	0.6261	0.1264	0.2327	0.109*	0.406 (12)
Cl1	0.37395 (13)	0.37873 (10)	0.10975 (10)	0.0736 (4)
O1	0.4321 (5)	0.2999 (4)	0.1393 (6)	0.141 (2)
N3	0.8879 (4)	0.0694 (3)	0.3295 (3)	0.0673 (11)
H3A	0.8725	0.0179	0.3008	0.081*	0.594 (12)
H3B	0.9256	0.0584	0.3861	0.081*	0.594 (12)
H3A'	0.9179	0.0152	0.3372	0.081*	0.406 (12)
H3B'	0.8869	0.0940	0.3871	0.081*	0.406 (12)
O2	0.4361 (8)	0.4352 (7)	0.0603 (7)	0.214 (5)
O3	0.2643 (9)	0.3764 (10)	0.130 (2)	0.235 (14)	0.594 (12)
C9	0.7735 (7)	0.1132 (8)	0.3445 (6)	0.0905 (17)	0.594 (12)
H9A	0.7243	0.0735	0.3790	0.109*	0.594 (12)
H9B	0.7904	0.1633	0.3849	0.109*	0.594 (12)
O3'	0.2863 (12)	0.3531 (10)	0.0330 (13)	0.118 (6)	0.406 (12)
C9'	0.7639 (7)	0.0630 (5)	0.2892 (9)	0.061 (4)	0.406 (12)
H9A'	0.7642	0.0260	0.2337	0.073*	0.406 (12)
H9B'	0.7167	0.0335	0.3350	0.073*	0.406 (12)
O4	0.364 (2)	0.4319 (9)	0.1837 (10)	0.337 (9)

	U11	U22	U33	U12	U13	U23
Zn1	0.0418 (4)	0.0565 (5)	0.0526 (5)	0.000	−0.0053 (3)	0.000
N1	0.0406 (19)	0.056 (2)	0.063 (2)	0.0001 (15)	−0.0033 (16)	0.0050 (17)
N2	0.0411 (19)	0.069 (2)	0.086 (3)	0.0064 (18)	0.0020 (19)	0.003 (2)
C1	0.050 (2)	0.051 (2)	0.060 (3)	−0.0044 (18)	−0.009 (2)	−0.004 (2)
C2	0.057 (3)	0.076 (3)	0.080 (4)	−0.005 (2)	−0.002 (3)	0.015 (3)
C3	0.076 (4)	0.074 (3)	0.092 (4)	−0.009 (3)	0.005 (3)	0.026 (3)
C4	0.094 (4)	0.062 (3)	0.075 (4)	0.001 (3)	−0.010 (3)	0.012 (3)
C5	0.077 (4)	0.053 (2)	0.074 (3)	0.008 (2)	−0.019 (3)	−0.003 (2)
C6	0.054 (3)	0.047 (2)	0.062 (3)	0.0038 (19)	−0.009 (2)	−0.009 (2)
C7	0.044 (2)	0.063 (3)	0.080 (3)	0.001 (2)	−0.001 (2)	0.012 (2)
C8	0.061 (3)	0.099 (3)	0.113 (4)	0.001 (2)	0.019 (3)	0.030 (3)
Cl1	0.0667 (9)	0.0818 (9)	0.0722 (9)	0.0043 (6)	0.0054 (7)	0.0076 (7)
O1	0.095 (4)	0.146 (5)	0.182 (6)	0.024 (4)	0.007 (4)	0.039 (4)
N3	0.064 (2)	0.073 (3)	0.065 (2)	−0.004 (2)	0.005 (2)	0.014 (2)
O2	0.172 (7)	0.230 (9)	0.236 (9)	−0.102 (7)	−0.023 (7)	0.106 (8)
O3	0.056 (6)	0.149 (11)	0.51 (4)	0.036 (6)	0.073 (12)	0.136 (18)
C9	0.061 (3)	0.099 (3)	0.113 (4)	0.001 (2)	0.019 (3)	0.030 (3)
O3'	0.048 (7)	0.149 (13)	0.152 (14)	0.004 (6)	−0.036 (7)	−0.047 (10)
C9'	0.055 (7)	0.056 (7)	0.072 (8)	−0.012 (5)	0.009 (6)	0.012 (6)
O4	0.57 (3)	0.241 (13)	0.207 (10)	−0.006 (16)	0.084 (15)	−0.121 (10)

Zn1—N1i	1.993 (4)	C8—H8A	0.9700
Zn1—N1	1.993 (4)	C8—H8B	0.9700
Zn1—N3i	2.036 (4)	C8—H8A'	0.9700
Zn1—N3	2.036 (4)	C8—H8B'	0.9700
N1—C7	1.335 (6)	C3—H3	0.9300
N1—C1	1.397 (6)	Cl1—O3	1.273 (10)
C5—C4	1.373 (9)	Cl1—O2	1.333 (7)
C5—C6	1.412 (7)	Cl1—O4	1.336 (10)
C5—H5	0.9300	Cl1—O1	1.423 (6)
C1—C2	1.389 (7)	Cl1—O3'	1.472 (12)
C1—C6	1.394 (6)	N3—C9'	1.468 (8)
C7—N2	1.347 (6)	N3—C9	1.468 (8)
C7—C8	1.484 (7)	N3—H3A	0.9000
C6—N2	1.372 (6)	N3—H3B	0.9000
N2—H2A	0.8600	N3—H3A'	0.9000
C2—C3	1.369 (8)	N3—H3B'	0.9000
C2—H2	0.9300	C9—H9A	0.9700
C4—C3	1.396 (8)	C9—H9B	0.9700
C4—H4	0.9300	C9'—H9A'	0.9700
C8—C9'	1.433 (7)	C9'—H9B'	0.9700
C8—C9	1.433 (7)
N1i—Zn1—N1	111.6 (2)	H8A—C8—H8B'	59.1
N1i—Zn1—N3i	97.02 (16)	H8B—C8—H8B'	50.4
N1—Zn1—N3i	118.10 (17)	H8A'—C8—H8B'	106.7
N1i—Zn1—N3	118.10 (17)	C2—C3—C4	122.1 (5)
N1—Zn1—N3	97.02 (16)	C2—C3—H3	119.0
N3i—Zn1—N3	116.3 (3)	C4—C3—H3	119.0
C7—N1—C1	106.1 (4)	O3—Cl1—O2	132.2 (7)
C7—N1—Zn1	123.1 (3)	O3—Cl1—O4	73.4 (14)
C1—N1—Zn1	130.6 (3)	O2—Cl1—O4	94.9 (10)
C4—C5—C6	115.4 (5)	O3—Cl1—O1	109.7 (6)
C4—C5—H5	122.3	O2—Cl1—O1	117.7 (6)
C6—C5—H5	122.3	O4—Cl1—O1	110.3 (9)
C2—C1—C6	120.9 (4)	O3—Cl1—O3'	63.5 (13)
C2—C1—N1	130.9 (4)	O2—Cl1—O3'	97.4 (9)
C6—C1—N1	108.2 (4)	O4—Cl1—O3'	131.1 (11)
N1—C7—N2	111.3 (4)	O1—Cl1—O3'	105.2 (7)
N1—C7—C8	125.6 (4)	C9'—N3—Zn1	114.5 (5)
N2—C7—C8	123.1 (4)	C9—N3—Zn1	113.9 (5)
N2—C6—C1	106.2 (4)	C9'—N3—H3A	67.4
N2—C6—C5	131.6 (5)	C9—N3—H3A	108.8
C1—C6—C5	122.2 (5)	Zn1—N3—H3A	108.8
C7—N2—C6	108.2 (4)	C9'—N3—H3B	135.6
C7—N2—H2A	125.9	C9—N3—H3B	108.8
C6—N2—H2A	125.9	Zn1—N3—H3B	108.8
C3—C2—C1	117.1 (5)	H3A—N3—H3B	107.7
C3—C2—H2	121.5	C9'—N3—H3A'	108.6
C1—C2—H2	121.5	C9—N3—H3A'	136.4
C5—C4—C3	122.4 (5)	Zn1—N3—H3A'	108.6
C5—C4—H4	118.8	H3A—N3—H3A'	45.8
C3—C4—H4	118.8	H3B—N3—H3A'	64.4
C9'—C8—C9	45.1 (7)	C9'—N3—H3B'	108.6
C9'—C8—C7	121.6 (6)	C9—N3—H3B'	67.7
C9—C8—C7	118.3 (6)	Zn1—N3—H3B'	108.6
C9'—C8—H8A	130.4	H3A—N3—H3B'	139.9
C9—C8—H8A	107.7	H3B—N3—H3B'	45.6
C7—C8—H8A	107.7	H3A'—N3—H3B'	107.6
C9'—C8—H8B	64.1	C8—C9—N3	117.6 (6)
C9—C8—H8B	107.7	C8—C9—H9A	107.9
C7—C8—H8B	107.7	N3—C9—H9A	107.9
H8A—C8—H8B	107.1	C8—C9—H9B	107.9
C9'—C8—H8A'	106.9	N3—C9—H9B	107.9
C9—C8—H8A'	65.3	H9A—C9—H9B	107.2
C7—C8—H8A'	106.9	C8—C9'—N3	117.6 (6)
H8A—C8—H8A'	49.3	C8—C9'—H9A'	107.9
H8B—C8—H8A'	143.1	N3—C9'—H9A'	107.9
C9'—C8—H8B'	106.9	C8—C9'—H9B'	107.9
C9—C8—H8B'	134.5	N3—C9'—H9B'	107.9
C7—C8—H8B'	106.9	H9A'—C9'—H9B'	107.2

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	2.09	2.946 (6)	174
N3—H3A···O4ii	0.90	2.12	2.953 (15)	154
C8—H8A···O1iii	0.97	2.42	3.210 (9)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	2.09	2.946 (6)	174
N3—H3A⋯O4i	0.90	2.12	2.953 (15)	154
C8—H8A⋯O1ii	0.97	2.42	3.210 (9)	138

Symmetry codes: (i) ; (ii) .