Dibromido[(S)-2-(pyrrolidin-2-yl)-1H-benzimidazole]zinc(II).

The title compound, [ZnBr(2)(C(11)H(13)N(3))], was synthesized by hydro-thermal reaction of ZnBr(2) and (S)-2-(pyrrolidin-2-yl)-1H-benzimidazole. The Zn(II) atom has a distorted tetra-hedral geometry and is coordinated by two N atoms from the chelating organic ligand and two terminal Br(-) anions. In the crystal structure, mol-ecules are linked into a chain along the [101] direction by N-H⋯Br and C-H⋯Br hydrogen bonds.

Related literature

For physical properties such as fluorescence and dielectric behaviors of metal-organic coordination compounds, see: Aminabhavi et al. (1986 ▶); Ye et al. (2008 ▶); Fu et al. (2007 ▶).

Experimental

Crystal data

[ZnBr2(C11H13N3)]

M = 412.43

Monoclinic,

a = 8.953 (3) Å

b = 11.668 (2) Å

c = 13.318 (2) Å

β = 91.443 (3)°

V = 1390.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 7.49 mm−1

T = 298 (2) K

0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.459, T max = 0.982 (expected range = 0.152–0.325)

13896 measured reflections

3179 independent reflections

2426 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.114

S = 0.99

3179 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −1.00 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019168/ci2621sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019168/ci2621Isup2.hkl

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

[ZnBr2(C11H13N3)]	F000 = 800
Mr = 412.43	Dx = 1.970 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3615 reflections
a = 8.953 (3) Å	θ = 2.7–27.5º
b = 11.668 (2) Å	µ = 7.49 mm−1
c = 13.318 (2) Å	T = 298 (2) K
β = 91.443 (3)º	Block, colourless
V = 1390.9 (6) Å3	0.30 × 0.25 × 0.15 mm
Z = 4

Rigaku Mercury2 diffractometer	3179 independent reflections
Radiation source: fine-focus sealed tube	2426 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.065
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 298(2) K	θmin = 2.7º
ω scans	h = −11→11
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.459, Tmax = 0.982	l = −17→17
13896 measured reflections

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.0563P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
3179 reflections	Δρmax = 0.67 e Å−3
154 parameters	Δρmin = −1.00 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Br1	0.25768 (6)	0.93780 (4)	0.57154 (4)	0.04999 (18)
Zn1	0.13105 (6)	0.76113 (4)	0.55176 (4)	0.03634 (16)
Br2	0.20151 (7)	0.62945 (5)	0.67586 (4)	0.0600 (2)
C6	0.1068 (5)	0.5895 (4)	0.2708 (3)	0.0378 (10)
N2	0.1146 (4)	0.6901 (3)	0.4143 (2)	0.0344 (8)
N1	−0.0955 (4)	0.7895 (3)	0.5261 (3)	0.0378 (8)
H10B	−0.1140	0.8650	0.5377	0.045*
N3	−0.0296 (4)	0.6401 (3)	0.2863 (3)	0.0391 (9)
H3C	−0.1073	0.6357	0.2471	0.047*
C8	0.3041 (6)	0.4841 (5)	0.2047 (4)	0.0554 (14)
H8A	0.3427	0.4362	0.1559	0.066*
C5	−0.0198 (5)	0.6977 (4)	0.3735 (3)	0.0315 (9)
C11	0.1978 (5)	0.6223 (4)	0.3510 (3)	0.0354 (9)
C7	0.1572 (6)	0.5177 (4)	0.1952 (3)	0.0489 (12)
H7A	0.0955	0.4941	0.1419	0.059*
C3	−0.2915 (5)	0.6980 (5)	0.4237 (4)	0.0550 (13)
H3A	−0.3632	0.7284	0.3748	0.066*
H3B	−0.2771	0.6170	0.4107	0.066*
C10	0.3458 (6)	0.5868 (5)	0.3582 (4)	0.0508 (12)
H10A	0.4074	0.6090	0.4120	0.061*
C9	0.3976 (6)	0.5188 (5)	0.2844 (4)	0.0555 (14)
H9A	0.4967	0.4949	0.2869	0.067*
C1	−0.1969 (6)	0.7209 (5)	0.5893 (3)	0.0512 (13)
H1A	−0.2104	0.7573	0.6539	0.061*
H1B	−0.1578	0.6442	0.6002	0.061*
C4	−0.1416 (5)	0.7637 (4)	0.4201 (3)	0.0361 (10)
H4A	−0.1568	0.8357	0.3834	0.043*
C2	−0.3426 (6)	0.7174 (6)	0.5290 (4)	0.0631 (15)
H2A	−0.4059	0.6553	0.5510	0.076*
H2B	−0.3965	0.7892	0.5344	0.076*

	U11	U22	U33	U12	U13	U23
Br1	0.0629 (3)	0.0386 (3)	0.0474 (3)	−0.0098 (2)	−0.0209 (2)	0.0027 (2)
Zn1	0.0395 (3)	0.0392 (3)	0.0299 (3)	−0.0022 (2)	−0.0093 (2)	−0.0028 (2)
Br2	0.0757 (4)	0.0521 (3)	0.0509 (3)	−0.0016 (3)	−0.0220 (3)	0.0139 (2)
C6	0.040 (2)	0.042 (2)	0.032 (2)	−0.001 (2)	−0.0023 (19)	−0.0055 (18)
N2	0.0326 (18)	0.041 (2)	0.0290 (17)	−0.0002 (16)	−0.0077 (15)	−0.0026 (15)
N1	0.041 (2)	0.0366 (19)	0.0357 (19)	−0.0010 (17)	−0.0034 (16)	−0.0067 (16)
N3	0.035 (2)	0.050 (2)	0.0319 (18)	−0.0031 (17)	−0.0084 (16)	−0.0051 (16)
C8	0.057 (3)	0.063 (3)	0.046 (3)	0.018 (3)	0.014 (3)	−0.013 (3)
C5	0.034 (2)	0.035 (2)	0.0255 (19)	−0.0055 (18)	−0.0032 (17)	0.0030 (17)
C11	0.031 (2)	0.041 (2)	0.033 (2)	−0.0023 (19)	−0.0051 (18)	−0.0002 (18)
C7	0.058 (3)	0.054 (3)	0.035 (2)	0.001 (3)	−0.004 (2)	−0.012 (2)
C3	0.035 (3)	0.077 (4)	0.053 (3)	−0.008 (3)	0.002 (2)	−0.015 (3)
C10	0.039 (3)	0.067 (3)	0.046 (3)	0.002 (3)	−0.008 (2)	−0.010 (2)
C9	0.041 (3)	0.076 (4)	0.050 (3)	0.014 (3)	0.004 (2)	−0.006 (3)
C1	0.048 (3)	0.068 (3)	0.038 (3)	−0.009 (3)	0.004 (2)	0.004 (2)
C4	0.033 (2)	0.044 (3)	0.031 (2)	0.0022 (19)	−0.0080 (18)	0.0031 (18)
C2	0.046 (3)	0.087 (4)	0.057 (3)	−0.002 (3)	0.002 (3)	0.004 (3)

Br1—Zn1	2.3642 (8)	C5—C4	1.484 (6)
Zn1—N2	2.011 (3)	C11—C10	1.390 (6)
Zn1—N1	2.075 (4)	C7—H7A	0.93
Zn1—Br2	2.3319 (7)	C3—C2	1.504 (7)
C6—N3	1.377 (6)	C3—C4	1.547 (6)
C6—C11	1.382 (6)	C3—H3A	0.97
C6—C7	1.393 (6)	C3—H3B	0.97
N2—C5	1.311 (5)	C10—C9	1.354 (7)
N2—C11	1.387 (5)	C10—H10A	0.93
N1—C1	1.488 (6)	C9—H9A	0.93
N1—C4	1.492 (5)	C1—C2	1.515 (7)
N1—H10B	0.91	C1—H1A	0.97
N3—C5	1.343 (5)	C1—H1B	0.97
N3—H3C	0.86	C4—H4A	0.98
C8—C7	1.376 (7)	C2—H2A	0.97
C8—C9	1.395 (7)	C2—H2B	0.97
C8—H8A	0.93
N2—Zn1—N1	82.35 (14)	C6—C7—H7A	122.2
N2—Zn1—Br2	112.70 (10)	C2—C3—C4	103.8 (4)
N1—Zn1—Br2	117.89 (10)	C2—C3—H3A	111.0
N2—Zn1—Br1	118.99 (11)	C4—C3—H3A	111.0
N1—Zn1—Br1	110.08 (11)	C2—C3—H3B	111.0
Br2—Zn1—Br1	112.03 (3)	C4—C3—H3B	111.0
N3—C6—C11	105.8 (4)	H3A—C3—H3B	109.0
N3—C6—C7	132.1 (4)	C9—C10—C11	118.0 (5)
C11—C6—C7	122.0 (4)	C9—C10—H10A	121.0
C5—N2—C11	106.7 (3)	C11—C10—H10A	121.0
C5—N2—Zn1	113.3 (3)	C10—C9—C8	120.8 (5)
C11—N2—Zn1	139.5 (3)	C10—C9—H9A	119.6
C1—N1—C4	105.6 (3)	C8—C9—H9A	119.6
C1—N1—Zn1	115.4 (3)	N1—C1—C2	104.1 (4)
C4—N1—Zn1	111.7 (3)	N1—C1—H1A	110.9
C1—N1—H10B	108.0	C2—C1—H1A	110.9
C4—N1—H10B	108.0	N1—C1—H1B	110.9
Zn1—N1—H10B	108.0	C2—C1—H1B	110.9
C5—N3—C6	107.8 (3)	H1A—C1—H1B	109.0
C5—N3—H3C	126.1	C5—C4—N1	108.1 (3)
C6—N3—H3C	126.1	C5—C4—C3	113.8 (4)
C7—C8—C9	122.8 (5)	N1—C4—C3	106.9 (3)
C7—C8—H8A	118.6	C5—C4—H4A	109.3
C9—C8—H8A	118.6	N1—C4—H4A	109.3
N2—C5—N3	111.4 (4)	C3—C4—H4A	109.3
N2—C5—C4	122.6 (4)	C3—C2—C1	102.7 (4)
N3—C5—C4	126.0 (4)	C3—C2—H2A	111.2
C6—C11—N2	108.2 (4)	C1—C2—H2A	111.2
C6—C11—C10	120.8 (4)	C3—C2—H2B	111.2
N2—C11—C10	130.9 (4)	C1—C2—H2B	111.2
C8—C7—C6	115.6 (4)	H2A—C2—H2B	109.1
C8—C7—H7A	122.2
N1—Zn1—N2—C5	2.2 (3)	Zn1—N2—C11—C6	170.4 (3)
Br2—Zn1—N2—C5	119.3 (3)	C5—N2—C11—C10	−179.8 (5)
Br1—Zn1—N2—C5	−106.5 (3)	Zn1—N2—C11—C10	−9.2 (8)
N1—Zn1—N2—C11	−168.0 (5)	C9—C8—C7—C6	0.1 (8)
Br2—Zn1—N2—C11	−50.9 (5)	N3—C6—C7—C8	179.6 (5)
Br1—Zn1—N2—C11	83.2 (5)	C11—C6—C7—C8	−1.4 (7)
N2—Zn1—N1—C1	110.8 (3)	C6—C11—C10—C9	−0.2 (8)
Br2—Zn1—N1—C1	−0.8 (3)	N2—C11—C10—C9	179.3 (5)
Br1—Zn1—N1—C1	−131.0 (3)	C11—C10—C9—C8	−1.1 (8)
N2—Zn1—N1—C4	−9.8 (3)	C7—C8—C9—C10	1.2 (9)
Br2—Zn1—N1—C4	−121.4 (3)	C4—N1—C1—C2	−32.6 (5)
Br1—Zn1—N1—C4	108.4 (3)	Zn1—N1—C1—C2	−156.5 (3)
C11—C6—N3—C5	−1.6 (5)	N2—C5—C4—N1	−14.3 (6)
C7—C6—N3—C5	177.5 (5)	N3—C5—C4—N1	166.5 (4)
C11—N2—C5—N3	−0.8 (5)	N2—C5—C4—C3	−132.8 (4)
Zn1—N2—C5—N3	−174.2 (3)	N3—C5—C4—C3	47.9 (6)
C11—N2—C5—C4	179.8 (4)	C1—N1—C4—C5	−111.7 (4)
Zn1—N2—C5—C4	6.5 (5)	Zn1—N1—C4—C5	14.4 (4)
C6—N3—C5—N2	1.5 (5)	C1—N1—C4—C3	11.1 (5)
C6—N3—C5—C4	−179.2 (4)	Zn1—N1—C4—C3	137.3 (3)
N3—C6—C11—N2	1.1 (5)	C2—C3—C4—C5	133.9 (4)
C7—C6—C11—N2	−178.1 (4)	C2—C3—C4—N1	14.6 (5)
N3—C6—C11—C10	−179.2 (4)	C4—C3—C2—C1	−34.0 (6)
C7—C6—C11—C10	1.6 (7)	N1—C1—C2—C3	41.8 (6)
C5—N2—C11—C6	−0.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3C···Br1i	0.86	2.74	3.516 (4)	150
C4—H4A···Br1ii	0.98	2.86	3.637 (5)	137
C1—H1A···Cg1iii	0.97	2.78	3.673 (6)	153

Br1—Zn1	2.3642 (8)
Zn1—N2	2.011 (3)
Zn1—N1	2.075 (4)
Zn1—Br2	2.3319 (7)

N2—Zn1—N1	82.35 (14)
N2—Zn1—Br2	112.70 (10)
N1—Zn1—Br2	117.89 (10)
N2—Zn1—Br1	118.99 (11)
N1—Zn1—Br1	110.08 (11)
Br2—Zn1—Br1	112.03 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3C⋯Br1i	0.86	2.74	3.516 (4)	150
C4—H4A⋯Br1ii	0.98	2.86	3.637 (5)	137
C1—H1A⋯Cg1iii	0.97	2.78	3.673 (6)	153

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C6–C11 ring.