Dibromido{2-[(4-nitro­phen­yl)imino­meth­yl]pyridine-κ2N,N′}zinc(II)

Salehzadeh, S.; Khalaj, M.; Dehghanpour, S.; Tarmoradi, I.

doi:10.1107/S1600536811042231

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1556

doi:10.1107/S1600536811042231

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Dibromido{2-[(4-nitrophenyl)iminomethyl]pyridine-κ²N,N′}zinc(II)

Sadegh Salehzadeh,^a ^* Mehdi Khalaj,^a Saeed Dehghanpour ^b and Isaac Tarmoradi ^a

^aFaculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran, and ^bDepartment of Chemistry, Alzahra University, PO Box 1993891176, Vanak, Tehran, Iran
^*Correspondence e-mail: saleh@basu.ac.ir

(Received 2 September 2011; accepted 12 October 2011; online 22 October 2011)

In the title compound, [ZnBr₂(C₁₂H₉N₃O₂)], the Zn^II ion is bonded to two Br ions and two N atoms of the diimine ligand in a distorted tetrahedral geometry. With the exception of the Br atoms, all other atoms are disordered over two sets of sites corresponding to a 180° rotation of the molecule along [ $[\overline{1}]$ 02]. The refined occupancies of the components are 0.809 (2) and 0.191 (2). In addition, the crystal studied was a non-merohedral twin with a refined component ratio of 0.343 (2):0.657 (2).

Related literature

For related structures, see: Khalaj et al. (2009 ). For background information on diimine complexes, see: Khalaj et al. (2010 ); Salehzadeh et al. (2011 ).

Experimental

Crystal data

[ZnBr₂(C₁₂H₉N₃O₂)]
M_r = 452.41
Triclinic, $[P \overline 1]$
a = 7.2614 (5) Å
b = 7.9228 (8) Å
c = 13.6436 (15) Å
α = 87.724 (4)°
β = 74.719 (6)°
γ = 82.007 (6)°
V = 749.81 (12) Å³
Z = 2
Mo Kα radiation
μ = 6.97 mm⁻¹
T = 150 K
0.28 × 0.15 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.417, T_max = 0.588
5868 measured reflections
3252 independent reflections
2630 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.140
S = 1.04
3252 reflections
237 parameters
48 restraints
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −1.24 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Br1—Zn1	2.3428 (14)
Br2—Zn1	2.3357 (16)
Zn1—N1	2.034 (9)
Zn1—N2	2.074 (7)

N1—Zn1—N2	81.2 (3)
N1—Zn1—Br2	116.1 (3)
N2—Zn1—Br2	118.0 (2)
N1—Zn1—Br1	112.3 (3)
N2—Zn1—Br1	111.5 (2)
Br2—Zn1—Br1	113.75 (5)

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811042231/gk2406sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042231/gk2406Isup2.hkl

checkCIF report

Comment top

In our ongoing studies on the synthesis, structural and spectroscopic characterization of transition metal complexes with diimine ligands Khalaj et al. (2010); Salehzadeh et al. (2011), we report herein the crystal structure of the title complex that was prepared by the reaction of ZnBr₂ with the bidentate ligand (4-nitrophenyl)-pyridine-2-ylmethylene-amine (Scheme I).

The molecluar structure of the title complex is shown in Fig. 1. The Zn^II ion is in a distorted tetrahedral environment formed by the chelating ligand and two Br ions. A comparison of the dihedral angles between the planes of the pyridine, chelate and the benzene ring indicates that the ligand is distorted from planarity, with twist of 22.23 (24)° between the chelate (N1C5C6N2) and the benzene (C7C8C9C10C11C12) planes. The Zn—Br and Zn—N bond dimensions compare well with the values found in other tetrahedral diimine complexes of zinc bromide (Khalaj et al., 2009).

Related literature top

For related structures, see: Khalaj et al. (2009). For background information on diimine complexes, see: Khalaj et al. (2010); Salehzadeh et al. (2011).

Experimental top

The title complex was prepared by the reaction of ZnBr₂ (22.5 mg, 0.1 mmol) and (4-nitrophenyl)pyridin-2-ylmethyleneamine (22.7 mg, 0.1 mmol) in 15 ml acetonitrile at room temperature. The solution was then concentrated under vacuum, and diffusion of diethyl ether vapor into the concentrated solution gave yellow crystals of the title compound in 60% yield.

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing both disordered components. The minor component is labeled with the suffix 'A'. The atoms Br1a and Br2a are related by the symmetry operation (x-1, y, x).

Dibromido{2-[(4-nitrophenyl)iminomethyl]pyridine- κ²N,N'}zinc(II) top

Crystal data top

[ZnBr₂(C₁₂H₉N₃O₂)]	Z = 2
M_r = 452.41	F(000) = 436
Triclinic, P1	D_x = 2.004 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2614 (5) Å	Cell parameters from 6572 reflections
b = 7.9228 (8) Å	θ = 2.6–27.5°
c = 13.6436 (15) Å	µ = 6.97 mm⁻¹
α = 87.724 (4)°	T = 150 K
β = 74.719 (6)°	Plate, colourless
γ = 82.007 (6)°	0.28 × 0.15 × 0.08 mm
V = 749.81 (12) Å³

Data collection top

Nonius KappaCCD diffractometer	3252 independent reflections
Radiation source: fine-focus sealed tube	2630 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
Detector resolution: 9 pixels mm^-1	θ_max = 27.6°, θ_min = 2.6°
ϕ scans and ω scans with κ offsets	h = −9→9
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −10→10
T_min = 0.417, T_max = 0.588	l = −9→17
5868 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0564P)² + 2.802P] where P = (F_o² + 2F_c²)/3
3252 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.70 e Å⁻³
48 restraints	Δρ_min = −1.24 e Å⁻³

Crystal data top

[ZnBr₂(C₁₂H₉N₃O₂)]	γ = 82.007 (6)°
M_r = 452.41	V = 749.81 (12) Å³
Triclinic, P1	Z = 2
a = 7.2614 (5) Å	Mo Kα radiation
b = 7.9228 (8) Å	µ = 6.97 mm⁻¹
c = 13.6436 (15) Å	T = 150 K
α = 87.724 (4)°	0.28 × 0.15 × 0.08 mm
β = 74.719 (6)°

Data collection top

Nonius KappaCCD diffractometer	3252 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	2630 reflections with I > 2σ(I)
T_min = 0.417, T_max = 0.588	R_int = 0.082
5868 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	48 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.04	Δρ_max = 0.70 e Å⁻³
3252 reflections	Δρ_min = −1.24 e Å⁻³
237 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	Occ. (<1)
Br1	0.33600 (13)	0.49862 (12)	0.72990 (8)	0.0358 (2)
Br2	0.43682 (13)	−0.00007 (12)	0.71961 (8)	0.0366 (3)
Zn1	0.20560 (17)	0.24153 (16)	0.74480 (11)	0.0259 (3)	0.809 (2)
O1	0.056 (2)	0.137 (2)	0.2086 (8)	0.036 (3)	0.809 (2)
O2	0.2084 (14)	0.3589 (19)	0.1962 (8)	0.034 (3)	0.809 (2)
N1	−0.0223 (12)	0.2369 (13)	0.8687 (7)	0.027 (2)	0.809 (2)
N2	−0.0123 (10)	0.2536 (11)	0.6714 (6)	0.0235 (16)	0.809 (2)
N3	0.1139 (15)	0.2531 (18)	0.2458 (5)	0.027 (2)	0.809 (2)
C1	−0.0292 (14)	0.2250 (15)	0.9678 (9)	0.032 (2)	0.809 (2)
H1A	0.0888	0.2123	0.9868	0.038*	0.809 (2)
C2	−0.2000 (15)	0.2302 (17)	1.0447 (9)	0.036 (3)	0.809 (2)
H2A	−0.1998	0.2239	1.1143	0.043*	0.809 (2)
C3	−0.3711 (15)	0.245 (2)	1.0150 (10)	0.038 (3)	0.809 (2)
H3A	−0.4906	0.2452	1.0647	0.046*	0.809 (2)
C4	−0.3672 (16)	0.259 (2)	0.9150 (10)	0.042 (3)	0.809 (2)
H4A	−0.4839	0.2762	0.8947	0.050*	0.809 (2)
C5	−0.1929 (19)	0.249 (2)	0.8435 (6)	0.029 (2)	0.809 (2)
C6	−0.1789 (12)	0.2637 (12)	0.7350 (8)	0.027 (2)	0.809 (2)
H6A	−0.2922	0.2807	0.7115	0.032*	0.809 (2)
C7	0.0079 (12)	0.2568 (13)	0.5649 (7)	0.022 (2)	0.809 (2)
C8	−0.1213 (16)	0.1964 (17)	0.5189 (8)	0.026 (2)	0.809 (2)
H8A	−0.2320	0.1533	0.5603	0.032*	0.809 (2)
C9	−0.091 (2)	0.198 (2)	0.4148 (11)	0.028 (3)	0.809 (2)
H9A	−0.1801	0.1597	0.3837	0.033*	0.809 (2)
C10	0.074 (3)	0.259 (2)	0.3573 (6)	0.023 (3)	0.809 (2)
C11	0.2013 (19)	0.3242 (17)	0.3996 (9)	0.024 (3)	0.809 (2)
H11A	0.3071	0.3731	0.3575	0.029*	0.809 (2)
C12	0.1737 (16)	0.3183 (16)	0.5044 (8)	0.027 (2)	0.809 (2)
H12A	0.2651	0.3551	0.5345	0.032*	0.809 (2)
Zn1A	−0.4500 (7)	0.2540 (7)	0.7425 (4)	0.0259 (3)	0.191 (2)
O1A	0.101 (12)	0.141 (12)	0.196 (3)	0.036 (3)	0.191 (2)
O2A	0.252 (8)	0.354 (10)	0.211 (3)	0.034 (3)	0.191 (2)
N1A	−0.349 (2)	0.259 (6)	0.8676 (10)	0.027 (2)	0.191 (2)
N2A	−0.1587 (13)	0.243 (4)	0.6709 (11)	0.0235 (16)	0.191 (2)
N3A	0.156 (7)	0.240 (8)	0.2468 (11)	0.027 (2)	0.191 (2)
C1A	−0.441 (3)	0.265 (6)	0.9666 (11)	0.032 (2)	0.191 (2)
H1AA	−0.5778	0.2718	0.9850	0.038*	0.191 (2)
C2A	−0.348 (4)	0.262 (8)	1.0440 (14)	0.036 (3)	0.191 (2)
H2AA	−0.4183	0.2797	1.1130	0.043*	0.191 (2)
C3A	−0.147 (4)	0.233 (9)	1.0156 (16)	0.038 (3)	0.191 (2)
H3AA	−0.0783	0.2113	1.0660	0.046*	0.191 (2)
C4A	−0.051 (3)	0.234 (10)	0.916 (2)	0.042 (3)	0.191 (2)
H4AA	0.0856	0.2229	0.8961	0.050*	0.191 (2)
C5A	−0.154 (3)	0.252 (7)	0.8437 (12)	0.029 (2)	0.191 (2)
C6A	−0.0591 (17)	0.252 (5)	0.7351 (15)	0.027 (2)	0.191 (2)
H6AA	0.0752	0.2576	0.7121	0.032*	0.191 (2)
C7A	−0.072 (2)	0.246 (4)	0.5645 (11)	0.022 (2)	0.191 (2)
C8A	0.108 (4)	0.298 (7)	0.5209 (16)	0.026 (2)	0.191 (2)
H8AA	0.1774	0.3375	0.5635	0.032*	0.191 (2)
C9A	0.187 (6)	0.292 (10)	0.4172 (18)	0.028 (3)	0.191 (2)
H9AA	0.3085	0.3294	0.3875	0.033*	0.191 (2)
C10A	0.083 (8)	0.231 (11)	0.3581 (11)	0.023 (3)	0.191 (2)
C11A	−0.090 (8)	0.169 (11)	0.3986 (17)	0.024 (3)	0.191 (2)
H11B	−0.1520	0.1210	0.3556	0.029*	0.191 (2)
C12A	−0.171 (5)	0.178 (8)	0.5029 (14)	0.027 (2)	0.191 (2)
H12B	−0.2923	0.1394	0.5319	0.032*	0.191 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0307 (5)	0.0262 (4)	0.0540 (6)	−0.0087 (3)	−0.0146 (5)	−0.0002 (5)
Br2	0.0281 (4)	0.0272 (4)	0.0537 (7)	−0.0054 (3)	−0.0079 (5)	−0.0030 (5)
Zn1	0.0226 (5)	0.0275 (5)	0.0292 (6)	−0.0083 (4)	−0.0068 (5)	−0.0006 (6)
O1	0.041 (9)	0.039 (4)	0.031 (5)	−0.007 (6)	−0.013 (4)	−0.010 (4)
O2	0.037 (7)	0.035 (4)	0.029 (5)	−0.010 (5)	−0.009 (4)	0.009 (4)
N1	0.028 (4)	0.024 (4)	0.031 (5)	−0.005 (3)	−0.008 (4)	0.001 (5)
N2	0.026 (4)	0.016 (4)	0.031 (4)	−0.004 (3)	−0.009 (4)	−0.004 (4)
N3	0.023 (6)	0.029 (4)	0.031 (4)	0.006 (5)	−0.013 (4)	−0.003 (5)
C1	0.026 (5)	0.032 (5)	0.040 (7)	−0.001 (4)	−0.013 (5)	0.003 (6)
C2	0.042 (6)	0.043 (7)	0.017 (5)	−0.007 (6)	0.003 (5)	−0.006 (6)
C3	0.018 (5)	0.065 (9)	0.028 (7)	−0.005 (5)	0.002 (5)	−0.008 (7)
C4	0.023 (5)	0.060 (8)	0.042 (8)	−0.010 (5)	−0.006 (6)	0.012 (8)
C5	0.026 (6)	0.029 (4)	0.034 (5)	−0.009 (5)	−0.008 (5)	−0.009 (5)
C6	0.023 (4)	0.023 (5)	0.037 (6)	−0.006 (4)	−0.011 (5)	0.001 (5)
C7	0.020 (6)	0.020 (4)	0.024 (4)	−0.002 (5)	−0.002 (4)	0.001 (4)
C8	0.025 (6)	0.022 (5)	0.030 (6)	−0.009 (4)	−0.001 (5)	0.000 (5)
C9	0.031 (6)	0.019 (8)	0.033 (7)	−0.004 (5)	−0.008 (5)	−0.007 (5)
C10	0.025 (4)	0.015 (8)	0.027 (4)	0.003 (4)	−0.006 (4)	0.001 (4)
C11	0.033 (6)	0.014 (6)	0.021 (6)	−0.005 (4)	0.001 (5)	0.002 (4)
C12	0.025 (6)	0.027 (5)	0.029 (6)	−0.011 (5)	−0.003 (4)	−0.001 (5)
Zn1A	0.0226 (5)	0.0275 (5)	0.0292 (6)	−0.0083 (4)	−0.0068 (5)	−0.0006 (6)
O1A	0.041 (9)	0.039 (4)	0.031 (5)	−0.007 (6)	−0.013 (4)	−0.010 (4)
O2A	0.037 (7)	0.035 (4)	0.029 (5)	−0.010 (5)	−0.009 (4)	0.009 (4)
N1A	0.028 (4)	0.024 (4)	0.031 (5)	−0.005 (3)	−0.008 (4)	0.001 (5)
N2A	0.026 (4)	0.016 (4)	0.031 (4)	−0.004 (3)	−0.009 (4)	−0.004 (4)
N3A	0.023 (6)	0.029 (4)	0.031 (4)	0.006 (5)	−0.013 (4)	−0.003 (5)
C1A	0.026 (5)	0.032 (5)	0.040 (7)	−0.001 (4)	−0.013 (5)	0.003 (6)
C2A	0.042 (6)	0.043 (7)	0.017 (5)	−0.007 (6)	0.003 (5)	−0.006 (6)
C3A	0.018 (5)	0.065 (9)	0.028 (7)	−0.005 (5)	0.002 (5)	−0.008 (7)
C4A	0.023 (5)	0.060 (8)	0.042 (8)	−0.010 (5)	−0.006 (6)	0.012 (8)
C5A	0.026 (6)	0.029 (4)	0.034 (5)	−0.009 (5)	−0.008 (5)	−0.009 (5)
C6A	0.023 (4)	0.023 (5)	0.037 (6)	−0.006 (4)	−0.011 (5)	0.001 (5)
C7A	0.020 (6)	0.020 (4)	0.024 (4)	−0.002 (5)	−0.002 (4)	0.001 (4)
C8A	0.025 (6)	0.022 (5)	0.030 (6)	−0.009 (4)	−0.001 (5)	0.000 (5)
C9A	0.031 (6)	0.019 (8)	0.033 (7)	−0.004 (5)	−0.008 (5)	−0.007 (5)
C10A	0.025 (4)	0.015 (8)	0.027 (4)	0.003 (4)	−0.006 (4)	0.001 (4)
C11A	0.033 (6)	0.014 (6)	0.021 (6)	−0.005 (4)	0.001 (5)	0.002 (4)
C12A	0.025 (6)	0.027 (5)	0.029 (6)	−0.011 (5)	−0.003 (4)	−0.001 (5)

Geometric parameters (Å, º) top

Br1—Zn1Aⁱ	2.340 (5)	C12—H12A	0.9500
Br1—Zn1	2.3428 (14)	Zn1A—N1A	2.033 (9)
Br2—Zn1	2.3357 (16)	Zn1A—N2A	2.074 (8)
Br2—Zn1Aⁱ	2.339 (5)	Zn1A—Br2ⁱⁱ	2.339 (5)
Zn1—N1	2.034 (9)	Zn1A—Br1ⁱⁱ	2.340 (5)
Zn1—N2	2.074 (7)	O1A—N3A	1.239 (10)
O1—N3	1.239 (10)	O2A—N3A	1.226 (10)
O2—N3	1.226 (10)	N1A—C1A	1.340 (14)
N1—C1	1.340 (14)	N1A—C5A	1.361 (16)
N1—C5	1.361 (16)	N2A—C6A	1.284 (11)
N2—C6	1.284 (11)	N2A—C7A	1.422 (12)
N2—C7	1.421 (12)	N3A—C10A	1.472 (10)
N3—C10	1.472 (10)	C1A—C2A	1.394 (14)
C1—C2	1.394 (14)	C1A—H1AA	0.9500
C1—H1A	0.9500	C2A—C3A	1.394 (15)
C2—C3	1.394 (15)	C2A—H2AA	0.9500
C2—H2A	0.9500	C3A—C4A	1.357 (18)
C3—C4	1.357 (18)	C3A—H3AA	0.9500
C3—H3A	0.9500	C4A—C5A	1.373 (16)
C4—C5	1.373 (16)	C4A—H4AA	0.9500
C4—H4A	0.9500	C5A—C6A	1.459 (14)
C5—C6	1.459 (14)	C6A—H6AA	0.9500
C6—H6A	0.9500	C7A—C8A	1.400 (14)
C7—C8	1.400 (14)	C7A—C12A	1.406 (12)
C7—C12	1.405 (12)	C8A—C9A	1.379 (18)
C8—C9	1.379 (18)	C8A—H8AA	0.9500
C8—H8A	0.9500	C9A—C10A	1.381 (18)
C9—C10	1.381 (18)	C9A—H9AA	0.9500
C9—H9A	0.9500	C10A—C11A	1.380 (19)
C10—C11	1.380 (19)	C11A—C12A	1.390 (16)
C11—C12	1.390 (16)	C11A—H11B	0.9500
C11—H11A	0.9500	C12A—H12B	0.9500

Zn1Aⁱ—Br1—Zn1	64.77 (11)	C7—C12—H12A	120.6
Zn1—Br2—Zn1Aⁱ	64.90 (12)	N1A—Zn1A—N2A	81.2 (3)
N1—Zn1—N2	81.2 (3)	N1A—Zn1A—Br2ⁱⁱ	114.8 (13)
N1—Zn1—Br2	116.1 (3)	N2A—Zn1A—Br2ⁱⁱ	110.8 (8)
N2—Zn1—Br2	118.0 (2)	N1A—Zn1A—Br1ⁱⁱ	111.9 (12)
N1—Zn1—Br1	112.3 (3)	N2A—Zn1A—Br1ⁱⁱ	120.6 (8)
N2—Zn1—Br1	111.5 (2)	Br2ⁱⁱ—Zn1A—Br1ⁱⁱ	113.73 (19)
Br2—Zn1—Br1	113.75 (5)	C1A—N1A—C5A	116.9 (9)
C1—N1—C5	117.0 (8)	C1A—N1A—Zn1A	130.7 (7)
C1—N1—Zn1	130.6 (7)	C5A—N1A—Zn1A	112.4 (7)
C5—N1—Zn1	112.4 (7)	C6A—N2A—C7A	121.1 (8)
C6—N2—C7	121.2 (7)	C6A—N2A—Zn1A	111.5 (6)
C6—N2—Zn1	111.5 (6)	C7A—N2A—Zn1A	127.0 (6)
C7—N2—Zn1	127.2 (5)	O2A—N3A—O1A	124.4 (8)
O2—N3—O1	124.5 (7)	O2A—N3A—C10A	117.9 (9)
O2—N3—C10	118.0 (9)	O1A—N3A—C10A	117.4 (9)
O1—N3—C10	117.5 (9)	N1A—C1A—C2A	123.4 (10)
N1—C1—C2	123.6 (10)	N1A—C1A—H1AA	118.3
N1—C1—H1A	118.2	C2A—C1A—H1AA	118.3
C2—C1—H1A	118.2	C1A—C2A—C3A	117.0 (12)
C1—C2—C3	117.2 (12)	C1A—C2A—H2AA	121.5
C1—C2—H2A	121.4	C3A—C2A—H2AA	121.5
C3—C2—H2A	121.4	C4A—C3A—C2A	119.8 (12)
C4—C3—C2	120.0 (11)	C4A—C3A—H3AA	120.1
C4—C3—H3A	120.0	C2A—C3A—H3AA	120.1
C2—C3—H3A	120.0	C3A—C4A—C5A	119.3 (11)
C3—C4—C5	119.4 (11)	C3A—C4A—H4AA	120.4
C3—C4—H4A	120.3	C5A—C4A—H4AA	120.4
C5—C4—H4A	120.3	N1A—C5A—C4A	122.7 (10)
N1—C5—C4	122.6 (10)	N1A—C5A—C6A	115.1 (9)
N1—C5—C6	115.1 (9)	C4A—C5A—C6A	122.1 (12)
C4—C5—C6	122.1 (11)	N2A—C6A—C5A	119.5 (9)
N2—C6—C5	119.5 (9)	N2A—C6A—H6AA	120.2
N2—C6—H6A	120.2	C5A—C6A—H6AA	120.2
C5—C6—H6A	120.2	C8A—C7A—C12A	119.9 (9)
C8—C7—C12	119.9 (8)	C8A—C7A—N2A	123.9 (8)
C8—C7—N2	123.9 (8)	C12A—C7A—N2A	116.0 (8)
C12—C7—N2	116.1 (8)	C9A—C8A—C7A	121.2 (10)
C9—C8—C7	121.2 (10)	C9A—C8A—H8AA	119.4
C9—C8—H8A	119.4	C7A—C8A—H8AA	119.4
C7—C8—H8A	119.4	C8A—C9A—C10A	117.6 (12)
C8—C9—C10	117.6 (11)	C8A—C9A—H9AA	121.2
C8—C9—H9A	121.2	C10A—C9A—H9AA	121.2
C10—C9—H9A	121.2	C11A—C10A—C9A	122.9 (9)
C11—C10—C9	122.9 (8)	C11A—C10A—N3A	118.6 (12)
C11—C10—N3	118.7 (12)	C9A—C10A—N3A	118.4 (13)
C9—C10—N3	118.4 (13)	C10A—C11A—C12A	119.5 (10)
C10—C11—C12	119.4 (9)	C10A—C11A—H11B	120.3
C10—C11—H11A	120.3	C12A—C11A—H11B	120.3
C12—C11—H11A	120.3	C11A—C12A—C7A	118.7 (10)
C11—C12—C7	118.7 (10)	C11A—C12A—H12B	120.6
C11—C12—H12A	120.6	C7A—C12A—H12B	120.6

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

Experimental details

Crystal data
Chemical formula	[ZnBr₂(C₁₂H₉N₃O₂)]
M_r	452.41
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	7.2614 (5), 7.9228 (8), 13.6436 (15)
α, β, γ (°)	87.724 (4), 74.719 (6), 82.007 (6)
V (Å³)	749.81 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	6.97
Crystal size (mm)	0.28 × 0.15 × 0.08

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.417, 0.588
No. of measured, independent and observed [I > 2σ(I)] reflections	5868, 3252, 2630
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.140, 1.04
No. of reflections	3252
No. of parameters	237
No. of restraints	48
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −1.24

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

Br1—Zn1	2.3428 (14)	Zn1—N1	2.034 (9)
Br2—Zn1	2.3357 (16)	Zn1—N2	2.074 (7)

N1—Zn1—N2	81.2 (3)	N1—Zn1—Br1	112.3 (3)
N1—Zn1—Br2	116.1 (3)	N2—Zn1—Br1	111.5 (2)
N2—Zn1—Br2	118.0 (2)	Br2—Zn1—Br1	113.75 (5)

Acknowledgements

The authors would like to acknowledge the Bu-Ali Sina and Alzahra University Research Councils for partial support of this work

References

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