(2,2′-Biquinoline-κ2N,N′)dibromido­zinc(II)

Saravani, H.; Rezvani, A.R.; Akbarzadeh Torbati, N.

doi:10.1107/S1600536810047434

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages m1622-m1623

https://doi.org/10.1107/S1600536810047434

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(2,2′-Biquinoline-κ²N,N′)dibromidozinc(II)

Hamideh Saravani,^a ^* Ali Reza Rezvani ^a and Niloufar Akbarzadeh Torbati ^a

^aDepartment of Chemistry, University of Sistan and Baluchestan, PO Box 98135-674, Zahedan, Iran
^*Correspondence e-mail: saravani@chem.usb.ac.ir

(Received 22 September 2010; accepted 16 November 2010; online 24 November 2010)

In the title compound, [ZnBr₂(C₁₈H₁₂N₂)], the Zn^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from the 2,2′-biquinoline ligand and two terminal Br atoms. The crystal packing is stabilized by weak intermolecular C—H⋯Br hydrogen bonds and extensive intermolecular π–π contacts between the pyridine and benzene rings [centroid–centroid distances = 3.775 (4), 3.748 (4), 3.735 (4), 3.538 (4), 3.678 (4) and 3.513 (4) Å].

Related literature

For Zn—Br and Zn—N bond lengths in related structures, see: Alizadeh et al. (2009 ), Muranishi et al. (2005 ). For complexes of 2,2′-biquinoline, see: Bowmaker et al. (2005 ); Butcher & Sinn (1977 ); Kou et al. (2008 ); Moreno et al. (2007 ); Okabe & Muranishi (2005 ); Rahimi et al. (2009 ); Yoshikawa et al. (2003 ); Zhou & Ng (2006 ).

Experimental

Crystal data

[ZnBr₂(C₁₈H₁₂N₂)]
M_r = 481.49
Monoclinic, P 2₁ /n
a = 7.9188 (16) Å
b = 12.351 (3) Å
c = 17.385 (4) Å
β = 103.01 (3)°
V = 1656.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 6.31 mm⁻¹
T = 298 K
0.20 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.380, T_max = 0.530
13476 measured reflections
4471 independent reflections
2968 reflections with I > 2σ(I)
R_int = 0.098

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.150
S = 1.15
4471 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 1.14 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N1—Zn1	2.063 (4)
N2—Zn1	2.056 (5)
Zn1—Br2	2.3348 (11)
Zn1—Br1	2.3498 (12)

N2—Zn1—N1	80.56 (18)
N2—Zn1—Br2	112.49 (14)
N1—Zn1—Br2	116.75 (13)
N2—Zn1—Br1	113.58 (14)
N1—Zn1—Br1	107.98 (15)
Br2—Zn1—Br1	119.24 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Br2ⁱ	0.93	2.87	3.574 (7)	133
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810047434/jj2062sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810047434/jj2062Isup2.hkl

checkCIF report

Comment top

Numerous complexes have been prepared with the bidentate ligand 2,2'-biquinoline (2,2'-biq) such as that of iron (Rahimi et al., 2009), iridium (Yoshikawa et al., 2003), platinum (Okabe & Muranishi 2005), copper (Moreno et al., 2007; Zhou & Ng 2006), silver (Bowmaker et al., 2005), nickel (Kou et al., 2008; Butcher & Sinn 1977) and palladium (Muranishi et al., 2005). For further investigation of 2,2'-biquinoline, we have synthesized the title compound, [ZnBr₂(C₁₈H₁₂N₂)].

In the title compound, the Zn^II atom is four-coordinate in a distorted tetrahedral configuration with two N atoms from one 2,2'-biquinoline and two terminal Br atoms (Fig. 1). The Zn—N and Zn—Br bond lengths and angles are within the normal ranges for [ZnCl₂(biq)] (Muranishi et al., 2005) and [ZnBr₂(6,6'-dmbpy)], (Alizadeh et al., 2009) [where 6,6'-dmbpy is 6,6'-dimethyl-2, 2'-bipyridine], respectively. Crystal stability is enhanced by weak intermolecular C—H···Br hydrogen bonds (Table 2, Fig.2) and extensive weak π—π intermolecular contacts between the mean planes of the pyridine and phenyl rings (Table 3).

Related literature top

For Zn—Br and Zn—N bond lengths in related structures, see: Alizadeh et al. (2009), Muranishi et al. (2005). For complexes of 2,2'-biquinoline, see: Bowmaker et al. (2005); Butcher & Sinn (1977); Kou et al. (2008); Moreno et al. (2007); Okabe & Muranishi (2005); Rahimi et al. (2009); Yoshikawa et al. (2003); Zhou et al. (2006).

Experimental top

For the preparation of the title compound, a solution of 2,2'- biquinoline (0.51 g, 2.0 mmol) in methanol (10 ml) and chloroform (10 ml) was added to a solution of ZnBr₂ (0.46 g, 2.0 mmol) in methanol (5 ml) and chloroform (5 ml) and the resulting solution was stirred for 20 min at room temperature. Suitable crystals for X-ray diffraction experiment were obtained by methanol diffusion into a solution in DMSO after one week (yield; 0.72 g, 74.8%).

Structure description top

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram for title molecule viewed down the a axis. Dashed lines indicate weak C—H···Br intermolecular interactions.

(2,2'-Biquinoline-κ²N,N')dibromidozinc(II) top

Crystal data top

[ZnBr₂(C₁₈H₁₂N₂)]	F(000) = 936
M_r = 481.49	D_x = 1.930 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 434 reflections
a = 7.9188 (16) Å	θ = 2.0–29.3°
b = 12.351 (3) Å	µ = 6.31 mm⁻¹
c = 17.385 (4) Å	T = 298 K
β = 103.01 (3)°	Block, colorless
V = 1656.7 (7) Å³	0.20 × 0.13 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4471 independent reflections
Radiation source: fine-focus sealed tube	2968 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.098
θ and ω scans	θ_max = 29.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −9→10
T_min = 0.380, T_max = 0.530	k = −16→16
13476 measured reflections	l = −23→23

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0538P)² + 1.2857P] where P = (F_o² + 2F_c²)/3
4471 reflections	(Δ/σ)_max = 0.007
208 parameters	Δρ_max = 1.14 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[ZnBr₂(C₁₈H₁₂N₂)]	V = 1656.7 (7) Å³
M_r = 481.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.9188 (16) Å	µ = 6.31 mm⁻¹
b = 12.351 (3) Å	T = 298 K
c = 17.385 (4) Å	0.20 × 0.13 × 0.10 mm
β = 103.01 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4471 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2968 reflections with I > 2σ(I)
T_min = 0.380, T_max = 0.530	R_int = 0.098
13476 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.15	Δρ_max = 1.14 e Å⁻³
4471 reflections	Δρ_min = −0.69 e Å⁻³
208 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
C1	0.7304 (8)	0.5440 (4)	0.0324 (4)	0.0354 (13)
C2	0.8156 (9)	0.4877 (5)	0.1012 (4)	0.0434 (14)
H2	0.8158	0.5152	0.1510	0.052*
C3	0.8975 (9)	0.3922 (5)	0.0933 (5)	0.0518 (18)
H3	0.9539	0.3547	0.1382	0.062*
C4	0.8974 (10)	0.3501 (5)	0.0183 (5)	0.0529 (18)
H4	0.9541	0.2851	0.0142	0.063*
C5	0.8161 (10)	0.4024 (5)	−0.0483 (5)	0.0488 (17)
H5	0.8161	0.3728	−0.0975	0.059*
C6	0.7312 (8)	0.5020 (5)	−0.0430 (4)	0.0386 (13)
C7	0.6441 (9)	0.5609 (5)	−0.1093 (4)	0.0428 (15)
H7	0.6430	0.5354	−0.1598	0.051*
C8	0.5609 (9)	0.6557 (5)	−0.1000 (3)	0.0424 (15)
H8	0.5021	0.6947	−0.1436	0.051*
C9	0.5666 (8)	0.6924 (5)	−0.0231 (3)	0.0317 (11)
C10	0.4705 (8)	0.7925 (4)	−0.0082 (3)	0.0313 (12)
C11	0.3551 (8)	0.8467 (5)	−0.0691 (4)	0.0383 (13)
H11	0.3384	0.8227	−0.1210	0.046*
C12	0.2681 (8)	0.9347 (5)	−0.0514 (4)	0.0409 (14)
H12	0.1921	0.9716	−0.0915	0.049*
C13	0.2924 (8)	0.9702 (5)	0.0272 (4)	0.0387 (13)
C14	0.2045 (10)	1.0612 (5)	0.0494 (5)	0.0489 (17)
H14	0.1258	1.0995	0.0113	0.059*
C15	0.2351 (11)	1.0923 (6)	0.1259 (5)	0.058 (2)
H15	0.1752	1.1510	0.1401	0.070*
C16	0.3560 (12)	1.0371 (6)	0.1841 (5)	0.0576 (19)
H16	0.3777	1.0610	0.2361	0.069*
C17	0.4432 (10)	0.9479 (6)	0.1651 (4)	0.0495 (17)
H17	0.5223	0.9110	0.2039	0.059*
C18	0.4100 (8)	0.9135 (5)	0.0853 (3)	0.0369 (13)
N1	0.6500 (7)	0.6402 (4)	0.0408 (3)	0.0312 (10)
N2	0.4991 (7)	0.8251 (4)	0.0668 (3)	0.0320 (10)
Zn1	0.67435 (10)	0.73002 (6)	0.14281 (4)	0.03680 (19)
Br1	0.95564 (10)	0.80280 (6)	0.17474 (5)	0.0561 (2)
Br2	0.55785 (11)	0.65496 (6)	0.24275 (4)	0.0554 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.039 (3)	0.029 (3)	0.041 (3)	−0.006 (2)	0.014 (3)	0.000 (2)
C2	0.043 (4)	0.044 (3)	0.044 (3)	0.001 (3)	0.010 (3)	0.007 (3)
C3	0.042 (4)	0.039 (3)	0.074 (5)	0.005 (3)	0.011 (4)	0.013 (3)
C4	0.045 (4)	0.031 (3)	0.086 (6)	0.001 (3)	0.019 (4)	−0.007 (3)
C5	0.053 (4)	0.039 (3)	0.059 (4)	−0.008 (3)	0.022 (4)	−0.016 (3)
C6	0.039 (3)	0.037 (3)	0.042 (3)	−0.008 (3)	0.015 (3)	−0.008 (3)
C7	0.055 (4)	0.039 (3)	0.035 (3)	−0.011 (3)	0.011 (3)	−0.016 (3)
C8	0.051 (4)	0.046 (3)	0.027 (3)	−0.011 (3)	0.003 (3)	−0.003 (3)
C9	0.035 (3)	0.032 (3)	0.026 (2)	−0.010 (2)	0.003 (2)	−0.003 (2)
C10	0.035 (3)	0.031 (3)	0.025 (2)	−0.006 (2)	0.001 (2)	0.001 (2)
C11	0.040 (3)	0.040 (3)	0.030 (3)	−0.007 (3)	−0.002 (2)	0.005 (2)
C12	0.037 (3)	0.039 (3)	0.042 (3)	0.001 (3)	0.000 (3)	0.010 (3)
C13	0.034 (3)	0.037 (3)	0.044 (3)	−0.002 (2)	0.008 (3)	0.003 (3)
C14	0.050 (4)	0.035 (3)	0.066 (5)	0.004 (3)	0.022 (4)	0.004 (3)
C15	0.063 (5)	0.052 (4)	0.071 (5)	0.009 (4)	0.039 (4)	−0.001 (4)
C16	0.074 (5)	0.058 (4)	0.046 (4)	0.010 (4)	0.025 (4)	−0.011 (3)
C17	0.065 (5)	0.052 (4)	0.034 (3)	0.003 (3)	0.015 (3)	−0.002 (3)
C18	0.046 (4)	0.030 (3)	0.035 (3)	−0.005 (2)	0.011 (3)	0.001 (2)
N1	0.038 (3)	0.028 (2)	0.027 (2)	−0.0014 (19)	0.0052 (19)	−0.0017 (18)
N2	0.040 (3)	0.030 (2)	0.026 (2)	0.002 (2)	0.0074 (19)	0.0012 (18)
Zn1	0.0467 (4)	0.0377 (3)	0.0234 (3)	0.0022 (3)	0.0023 (3)	0.0002 (3)
Br1	0.0502 (4)	0.0611 (4)	0.0508 (4)	−0.0085 (3)	−0.0019 (3)	−0.0033 (3)
Br2	0.0760 (5)	0.0629 (4)	0.0263 (3)	−0.0154 (4)	0.0095 (3)	0.0018 (3)

Geometric parameters (Å, º) top

C1—N1	1.371 (7)	C11—C12	1.359 (9)
C1—C6	1.412 (8)	C11—H11	0.9300
C1—C2	1.416 (9)	C12—C13	1.407 (9)
C2—C3	1.368 (10)	C12—H12	0.9300
C2—H2	0.9300	C13—C18	1.399 (9)
C3—C4	1.404 (11)	C13—C14	1.420 (9)
C3—H3	0.9300	C14—C15	1.353 (11)
C4—C5	1.355 (11)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.403 (12)
C5—C6	1.415 (9)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.379 (10)
C6—C7	1.405 (9)	C16—H16	0.9300
C7—C8	1.371 (10)	C17—C18	1.417 (9)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.403 (8)	C18—N2	1.376 (8)
C8—H8	0.9300	N1—Zn1	2.063 (4)
C9—N1	1.325 (7)	N2—Zn1	2.056 (5)
C9—C10	1.504 (8)	Zn1—Br2	2.3348 (11)
C10—N2	1.334 (7)	Zn1—Br1	2.3498 (12)
C10—C11	1.404 (8)

N1—C1—C6	121.1 (6)	C11—C12—C13	120.2 (6)
N1—C1—C2	118.8 (6)	C11—C12—H12	119.9
C6—C1—C2	120.1 (6)	C13—C12—H12	119.9
C3—C2—C1	119.1 (7)	C18—C13—C12	118.0 (6)
C3—C2—H2	120.4	C18—C13—C14	119.2 (6)
C1—C2—H2	120.4	C12—C13—C14	122.9 (6)
C2—C3—C4	120.7 (7)	C15—C14—C13	120.1 (7)
C2—C3—H3	119.6	C15—C14—H14	119.9
C4—C3—H3	119.6	C13—C14—H14	119.9
C5—C4—C3	121.2 (6)	C14—C15—C16	120.8 (7)
C5—C4—H4	119.4	C14—C15—H15	119.6
C3—C4—H4	119.4	C16—C15—H15	119.6
C4—C5—C6	120.1 (7)	C17—C16—C15	120.9 (7)
C4—C5—H5	120.0	C17—C16—H16	119.6
C6—C5—H5	120.0	C15—C16—H16	119.6
C7—C6—C1	117.9 (5)	C16—C17—C18	118.8 (7)
C7—C6—C5	123.3 (6)	C16—C17—H17	120.6
C1—C6—C5	118.8 (6)	C18—C17—H17	120.6
C8—C7—C6	120.3 (6)	N2—C18—C13	121.4 (5)
C8—C7—H7	119.8	N2—C18—C17	118.3 (6)
C6—C7—H7	119.8	C13—C18—C17	120.2 (6)
C7—C8—C9	118.4 (6)	C9—N1—C1	119.3 (5)
C7—C8—H8	120.8	C9—N1—Zn1	113.0 (4)
C9—C8—H8	120.8	C1—N1—Zn1	127.0 (4)
N1—C9—C8	123.0 (6)	C10—N2—C18	119.0 (5)
N1—C9—C10	115.6 (5)	C10—N2—Zn1	113.4 (4)
C8—C9—C10	121.4 (5)	C18—N2—Zn1	127.6 (4)
N2—C10—C11	122.1 (5)	N2—Zn1—N1	80.56 (18)
N2—C10—C9	115.8 (5)	N2—Zn1—Br2	112.49 (14)
C11—C10—C9	122.0 (5)	N1—Zn1—Br2	116.75 (13)
C12—C11—C10	119.2 (6)	N2—Zn1—Br1	113.58 (14)
C12—C11—H11	120.4	N1—Zn1—Br1	107.98 (15)
C10—C11—H11	120.4	Br2—Zn1—Br1	119.24 (4)

N1—C1—C2—C3	−179.4 (6)	C12—C13—C18—C17	178.1 (6)
C6—C1—C2—C3	−0.3 (9)	C14—C13—C18—C17	−1.2 (9)
C1—C2—C3—C4	−0.1 (10)	C16—C17—C18—N2	179.3 (6)
C2—C3—C4—C5	−0.2 (11)	C16—C17—C18—C13	0.8 (10)
C3—C4—C5—C6	0.8 (11)	C8—C9—N1—C1	−2.2 (9)
N1—C1—C6—C7	−1.2 (9)	C10—C9—N1—C1	175.3 (5)
C2—C1—C6—C7	179.8 (6)	C8—C9—N1—Zn1	168.5 (5)
N1—C1—C6—C5	180.0 (6)	C10—C9—N1—Zn1	−13.9 (6)
C2—C1—C6—C5	0.9 (9)	C6—C1—N1—C9	2.4 (8)
C4—C5—C6—C7	−179.9 (7)	C2—C1—N1—C9	−178.5 (6)
C4—C5—C6—C1	−1.2 (10)	C6—C1—N1—Zn1	−166.9 (4)
C1—C6—C7—C8	−0.4 (9)	C2—C1—N1—Zn1	12.2 (8)
C5—C6—C7—C8	178.4 (6)	C11—C10—N2—C18	1.3 (8)
C6—C7—C8—C9	0.6 (9)	C9—C10—N2—C18	−177.3 (5)
C7—C8—C9—N1	0.7 (9)	C11—C10—N2—Zn1	180.0 (4)
C7—C8—C9—C10	−176.7 (6)	C9—C10—N2—Zn1	1.4 (6)
N1—C9—C10—N2	8.6 (7)	C13—C18—N2—C10	−0.8 (8)
C8—C9—C10—N2	−173.8 (5)	C17—C18—N2—C10	−179.3 (6)
N1—C9—C10—C11	−170.0 (5)	C13—C18—N2—Zn1	−179.3 (4)
C8—C9—C10—C11	7.6 (9)	C17—C18—N2—Zn1	2.3 (8)
N2—C10—C11—C12	−0.6 (9)	C10—N2—Zn1—N1	−6.6 (4)
C9—C10—C11—C12	177.9 (5)	C18—N2—Zn1—N1	171.8 (5)
C10—C11—C12—C13	−0.6 (9)	C10—N2—Zn1—Br2	−121.8 (4)
C11—C12—C13—C18	1.1 (9)	C18—N2—Zn1—Br2	56.7 (5)
C11—C12—C13—C14	−179.6 (6)	C10—N2—Zn1—Br1	99.0 (4)
C18—C13—C14—C15	0.2 (10)	C18—N2—Zn1—Br1	−82.6 (5)
C12—C13—C14—C15	−179.1 (7)	C9—N1—Zn1—N2	11.4 (4)
C13—C14—C15—C16	1.3 (12)	C1—N1—Zn1—N2	−178.7 (5)
C14—C15—C16—C17	−1.8 (13)	C9—N1—Zn1—Br2	121.9 (4)
C15—C16—C17—C18	0.7 (12)	C1—N1—Zn1—Br2	−68.2 (5)
C12—C13—C18—N2	−0.4 (9)	C9—N1—Zn1—Br1	−100.4 (4)
C14—C13—C18—N2	−179.7 (5)	C1—N1—Zn1—Br1	69.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Br2ⁱ	0.93	2.87	3.574 (7)	133

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

Experimental details

Crystal data
Chemical formula	[ZnBr₂(C₁₈H₁₂N₂)]
M_r	481.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.9188 (16), 12.351 (3), 17.385 (4)
β (°)	103.01 (3)
V (Å³)	1656.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.31
Crystal size (mm)	0.20 × 0.13 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.380, 0.530
No. of measured, independent and observed [I > 2σ(I)] reflections	13476, 4471, 2968
R_int	0.098
(sin θ/λ)_max (Å⁻¹)	0.689

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.150, 1.15
No. of reflections	4471
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.14, −0.69

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

N1—Zn1	2.063 (4)	Zn1—Br2	2.3348 (11)
N2—Zn1	2.056 (5)	Zn1—Br1	2.3498 (12)

N2—Zn1—N1	80.56 (18)	N2—Zn1—Br1	113.58 (14)
N2—Zn1—Br2	112.49 (14)	N1—Zn1—Br1	107.98 (15)
N1—Zn1—Br2	116.75 (13)	Br2—Zn1—Br1	119.24 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Br2ⁱ	0.930	2.870	3.574 (7)	133.00

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

Cg···Cg π—π interactions [Cg1, Cg2, Cg3, Cg5, Cg5 = centroids of rings Zn1/N1/C9/C10/N2; N1/C1/C6/C7/C8/C9; N2/C10/C11/C12/C13/C18; C1–C6; C13–C18; Symmetry codes: (i) 1-x, 1-y, -z; (ii) 1-x, 2-y, -z; (iii) 2-x, 1-y, -z]
Cg(I) Cg(J) Cg···Cg (Å) top

Cg1	Cg4	3.775 (4)ⁱ
Cg2	Cg2	3.748 (4)ⁱ
Cg2	Cg4	3.735 (4)ⁱ
Cg3	Cg3	3.538 (4)ⁱⁱ
Cg3	Cg5	3.678 (4)ⁱⁱ
Cg4	Cg4	3.513 (4)ⁱⁱⁱ

Acknowledgements

We are grateful to the University of Sistan and Baluchestan for financial support.

References

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