Dibromido(2,3,5,6-tetra-2-pyridyl­pyrazine-κ3N2,N1,N6)zinc(II)

Ahmadi, R.; Kalateh, K.; Amani, V.

doi:10.1107/S1600536810027820

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages m959-m960

https://doi.org/10.1107/S1600536810027820

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Dibromido(2,3,5,6-tetra-2-pyridylpyrazine-κ³N²,N¹,N⁶)zinc(II)

Roya Ahmadi,^a Khadijeh Kalateh ^a and Vahid Amani ^a ^*

^aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran
^*Correspondence e-mail: v_amani2002@yahoo.com

(Received 11 July 2010; accepted 13 July 2010; online 17 July 2010)

In the title compound, [ZnBr₂(C₂₄H₁₆N₆)], the Zn^II ion is coordinated by the N,N′,N′′-tridentate 2,3,5,6-tetra-2-pyridylpyrazine ligand and two bromide ions, generating a distorted ZnN₃Br₂ trigonal-bipyramidal geometry for the metal ion, with both bromide ions in equatorial sites. The dihedral angles between the pyrazine ring and the coordinated pyridine rings are 13.3 (2) and 24.8 (2)°; those between the pyrazine ring and the uncoordinated pyradine rings are 31.3 (2) and 44.2 (2)°. In the crystal, inversion dimers linked by pairs of weak C—H⋯Br hydrogen bonds occur.

Related literature

For the synthesis of the ligand, see: Goodwin & Lyons (1959 ). For the structure of the free ligand, see Bock et al. (1992 ); Greaves & Stoeckli-Evans (1992 ). For related structures, see: Alizadeh et al. (2009 ); Carranza et al. (2004 ); Graf et al. (1993 , 1997 ); Hadadzadeh et al. (2006 ); Laine et al. (1995 ); Morsali & Ramazani (2005 ); Sakai & Kurashima (2003 ); Seyed Sadjadi et al. (2008 ); Yamada et al. (2000 ); Zhang et al. (2005 ).

Experimental

Crystal data

[ZnBr₂(C₂₄H₁₆N₆)]
M_r = 613.62
Triclinic, $[P \overline 1]$
a = 10.3985 (8) Å
b = 10.5378 (8) Å
c = 12.3034 (10) Å
α = 64.898 (6)°
β = 83.187 (6)°
γ = 77.901 (6)°
V = 1193.05 (16) Å³
Z = 2
Mo Kα radiation
μ = 4.40 mm⁻¹
T = 298 K
0.50 × 0.40 × 0.28 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.206, T_max = 0.369
13823 measured reflections
6412 independent reflections
4954 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.126
S = 1.14
6412 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.89 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—N2	2.151 (3)
Zn1—N6	2.177 (3)
Zn1—N1	2.202 (3)
Zn1—Br1	2.3692 (7)
Zn1—Br2	2.3880 (6)

N2—Zn1—N6	73.75 (10)
N2—Zn1—N1	72.96 (11)
N6—Zn1—N1	146.71 (11)
N2—Zn1—Br1	125.38 (8)
N6—Zn1—Br1	102.12 (9)
N1—Zn1—Br1	97.43 (10)
N2—Zn1—Br2	118.61 (8)
N6—Zn1—Br2	97.55 (9)
N1—Zn1—Br2	97.76 (10)
Br1—Zn1—Br2	115.93 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Br2ⁱ	0.93	2.88	3.791 (7)	166
Symmetry code: (i) -x+2, -y+1, -z+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: SHELXTL; software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810027820/hb5552sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027820/hb5552Isup2.hkl

checkCIF report

Comment top

Goodwin & Lyons (1959) reported the synthesis of 2,3,5,6-tetra(2-pyridinyl)pyrazine (tppz). Bock et al. (1992) and Greaves & Stoeckli-Evans (1992) determined the structure of tppz by single-crystal X-ray diffraction methods. tppz is a good bis-tridentate bridging ligand, and numerous complexes with tppz have been prepared, such as that of ruthenium (Hadadzadeh et al., 2006), platinum (Sakai & Kurashima, 2003), mercury (Zhang et al., 2005), copper (Carranza et al., 2004), iron (Laine et al., 1995), nickel (Graf et al., 1997), palladium (Yamada et al., 2000), cadmium (Seyed Sadjadi et al., 2008) and lead (Morsali & Ramazani, 2005). For further investigation of 2,3,5,6-tetra(2-pyridinyl)pyrazine, we synthesis the title complex, (I), and report herein its crystal structure.

In the title compound, (Fig. 1), the Zn^II atom is five-coordinated in a distorted trigonal-bipyramidal configuration by three N atoms from one 2,3,5,6-tetra(2-pyridinyl)pyrazine and two terminal Br. The Zn—N and Zn—Br bond lengths and angles (Table 1) are within normal range of [ZnCl₂ (tppz)], (Graf et al., 1993) and [ZnBr₂(6,6'-dmbpy)], (Alizadeh et al., 2009) [where 6,6'-dmbpy is 6,6'-dimethyl-2, 2'-bipyridine] respectively.

In the crystal structure, intermolecular C—H···Br hydrogen bonds (Table 2, Fig. 2) may stabilize the structure.

Related literature top

For the synthesis of the ligand, see: Goodwin & Lyons (1959). For the structure of the free ligand, see Bock et al. (1992); Greaves & Stoeckli-Evans (1992). For related structures, see: Alizadeh et al. (2009); Carranza et al. (2004); Graf et al. (1993, 1997); Hadadzadeh et al. (2006); Laine et al. (1995); Morsali & Ramazani (2005); Sakai & Kurashima (2003); Seyed Sadjadi et al. (2008); Yamada et al. (2000); Zhang et al. (2005).

Experimental top

A solution of 2,3,5,6-tetra(2-pyridinyl)pyrazine (0.40 g, 1.00 mmol) in HCCl₃ (20 ml) was added to a solution of ZnBr₂ (0.23 g, 1.00 mmol) in methanol (20 ml) at room temperature. The suitable crystals for X-ray diffraction experiment were obtained by methanol diffusion to a colorless solution in DMSO. Yellow prisms of (I) were isolated after one week (yield; 0.45 g, 73.3%).

Structure description top

In the crystal structure, intermolecular C—H···Br hydrogen bonds (Table 2, Fig. 2) may stabilize the structure.

For the synthesis of the ligand, see: Goodwin & Lyons (1959). For the structure of the free ligand, see Bock et al. (1992); Greaves & Stoeckli-Evans (1992). For related structures, see: Alizadeh et al. (2009); Carranza et al. (2004); Graf et al. (1993, 1997); Hadadzadeh et al. (2006); Laine et al. (1995); Morsali & Ramazani (2005); Sakai & Kurashima (2003); Seyed Sadjadi et al. (2008); Yamada et al. (2000); Zhang et al. (2005).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Unit-cell packing diagram for (I).

Dibromido(2,3,5,6-tetra-2-pyridylpyrazine- κ³N²,N¹,N⁶)zinc(II) top

Crystal data top

[ZnBr₂(C₂₄H₁₆N₆)]	Z = 2
M_r = 613.62	F(000) = 604
Triclinic, P1	D_x = 1.708 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3985 (8) Å	Cell parameters from 998 reflections
b = 10.5378 (8) Å	θ = 1.8–29.3°
c = 12.3034 (10) Å	µ = 4.40 mm⁻¹
α = 64.898 (6)°	T = 298 K
β = 83.187 (6)°	Prism, yellow
γ = 77.901 (6)°	0.50 × 0.40 × 0.28 mm
V = 1193.05 (16) Å³

Data collection top

Bruker SMART CCD diffractometer	6412 independent reflections
Radiation source: fine-focus sealed tube	4954 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
phi and ω scans	θ_max = 29.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −14→14
T_min = 0.206, T_max = 0.369	k = −13→14
13823 measured reflections	l = −16→16

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0524P)² + 0.8386P] where P = (F_o² + 2F_c²)/3
6412 reflections	(Δ/σ)_max = 0.010
298 parameters	Δρ_max = 0.89 e Å⁻³
0 restraints	Δρ_min = −0.91 e Å⁻³

Crystal data top

[ZnBr₂(C₂₄H₁₆N₆)]	γ = 77.901 (6)°
M_r = 613.62	V = 1193.05 (16) Å³
Triclinic, P1	Z = 2
a = 10.3985 (8) Å	Mo Kα radiation
b = 10.5378 (8) Å	µ = 4.40 mm⁻¹
c = 12.3034 (10) Å	T = 298 K
α = 64.898 (6)°	0.50 × 0.40 × 0.28 mm
β = 83.187 (6)°

Data collection top

Bruker SMART CCD diffractometer	6412 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	4954 reflections with I > 2σ(I)
T_min = 0.206, T_max = 0.369	R_int = 0.049
13823 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.14	Δρ_max = 0.89 e Å⁻³
6412 reflections	Δρ_min = −0.91 e Å⁻³
298 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
Zn1	0.69495 (4)	0.37649 (4)	0.71272 (4)	0.03753 (11)
Br2	0.62972 (5)	0.62861 (4)	0.64284 (4)	0.05470 (13)
Br1	0.52355 (5)	0.24651 (6)	0.74414 (5)	0.07140 (16)
N5	1.1123 (3)	0.0445 (4)	0.5766 (3)	0.0452 (7)
N3	1.1520 (3)	0.1584 (3)	0.7992 (3)	0.0397 (6)
C7	1.0799 (3)	0.2101 (4)	0.8729 (3)	0.0379 (7)
C20	0.9186 (3)	0.3265 (3)	0.5446 (3)	0.0352 (7)
C16	1.3156 (3)	0.0461 (4)	0.6499 (3)	0.0397 (7)
H16	1.3598	0.0784	0.6918	0.048*
C6	0.9439 (3)	0.2551 (4)	0.8580 (3)	0.0350 (7)
C17	1.1801 (3)	0.0874 (4)	0.6368 (3)	0.0363 (7)
N6	0.7888 (3)	0.3729 (3)	0.5459 (3)	0.0407 (7)
N2	0.8986 (3)	0.2850 (3)	0.7503 (2)	0.0339 (6)
C8	1.1517 (4)	0.2208 (4)	0.9655 (3)	0.0423 (8)
C19	0.9768 (3)	0.2574 (4)	0.6653 (3)	0.0341 (6)
C5	0.8400 (4)	0.2731 (4)	0.9463 (3)	0.0377 (7)
C18	1.1009 (3)	0.1719 (4)	0.6992 (3)	0.0353 (7)
N4	1.1146 (3)	0.3429 (4)	0.9781 (3)	0.0457 (7)
N1	0.7200 (3)	0.3285 (4)	0.9022 (3)	0.0475 (7)
C13	1.1800 (4)	−0.0388 (5)	0.5255 (4)	0.0499 (9)
H13	1.1346	−0.0669	0.4811	0.060*
C15	1.3823 (4)	−0.0435 (4)	0.5994 (3)	0.0453 (8)
H15	1.4724	−0.0751	0.6087	0.054*
C21	0.9930 (4)	0.3513 (4)	0.4381 (3)	0.0448 (8)
H21	1.0837	0.3210	0.4388	0.054*
C3	0.7577 (5)	0.2571 (5)	1.1400 (4)	0.0567 (11)
H3	0.7711	0.2326	1.2204	0.068*
C23	0.7940 (5)	0.4678 (5)	0.3319 (4)	0.0584 (11)
H23	0.7493	0.5150	0.2605	0.070*
C12	1.1751 (5)	0.3588 (5)	1.0604 (4)	0.0592 (11)
H12	1.1516	0.4439	1.0696	0.071*
C1	0.6194 (5)	0.3486 (6)	0.9748 (4)	0.0646 (13)
H1	0.5356	0.3851	0.9440	0.078*
C22	0.9278 (5)	0.4225 (5)	0.3307 (3)	0.0525 (10)
H22	0.9746	0.4396	0.2581	0.063*
C9	1.2494 (5)	0.1128 (6)	1.0304 (5)	0.0731 (16)
H9	1.2749	0.0302	1.0174	0.088*
C24	0.7276 (4)	0.4421 (5)	0.4402 (4)	0.0548 (10)
H24	0.6371	0.4735	0.4410	0.066*
C2	0.6354 (5)	0.3171 (6)	1.0948 (4)	0.0660 (13)
H2	0.5648	0.3364	1.1427	0.079*
C11	1.2693 (7)	0.2565 (7)	1.1313 (6)	0.0866 (19)
H11	1.3067	0.2706	1.1893	0.104*
C10	1.3082 (7)	0.1332 (8)	1.1165 (7)	0.103 (3)
H10	1.3737	0.0629	1.1635	0.123*
C14	1.3150 (4)	−0.0862 (4)	0.5348 (4)	0.0486 (9)
H14	1.3587	−0.1453	0.4983	0.058*
C4	0.8616 (4)	0.2330 (5)	1.0660 (3)	0.0488 (9)
H4	0.9450	0.1903	1.0964	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03347 (19)	0.0393 (2)	0.0397 (2)	0.00120 (15)	−0.00453 (14)	−0.01878 (17)
Br2	0.0683 (3)	0.0393 (2)	0.0545 (2)	0.00334 (18)	−0.00494 (19)	−0.02253 (18)
Br1	0.0635 (3)	0.0628 (3)	0.0887 (4)	−0.0252 (2)	−0.0112 (2)	−0.0232 (3)
N5	0.0386 (15)	0.0507 (18)	0.0572 (19)	0.0007 (13)	−0.0060 (13)	−0.0352 (16)
N3	0.0376 (14)	0.0409 (16)	0.0463 (16)	0.0017 (12)	−0.0089 (12)	−0.0254 (13)
C7	0.0416 (17)	0.0347 (16)	0.0412 (17)	0.0010 (13)	−0.0091 (14)	−0.0208 (14)
C20	0.0408 (17)	0.0304 (15)	0.0355 (16)	−0.0001 (13)	−0.0045 (13)	−0.0167 (13)
C16	0.0341 (16)	0.0428 (19)	0.0438 (18)	−0.0068 (14)	0.0001 (13)	−0.0196 (15)
C6	0.0415 (17)	0.0304 (15)	0.0329 (15)	−0.0010 (13)	−0.0051 (12)	−0.0143 (13)
C17	0.0326 (15)	0.0370 (17)	0.0432 (17)	−0.0034 (13)	−0.0016 (13)	−0.0213 (14)
N6	0.0410 (15)	0.0462 (17)	0.0352 (14)	0.0037 (13)	−0.0065 (11)	−0.0209 (13)
N2	0.0347 (13)	0.0361 (14)	0.0325 (13)	−0.0015 (11)	−0.0033 (10)	−0.0171 (11)
C8	0.0427 (18)	0.046 (2)	0.0423 (18)	−0.0025 (15)	−0.0101 (14)	−0.0226 (16)
C19	0.0357 (15)	0.0329 (16)	0.0375 (16)	−0.0008 (12)	−0.0026 (12)	−0.0201 (13)
C5	0.0475 (18)	0.0317 (16)	0.0321 (15)	−0.0049 (14)	−0.0008 (13)	−0.0124 (13)
C18	0.0331 (15)	0.0352 (16)	0.0409 (17)	−0.0011 (13)	−0.0040 (12)	−0.0202 (14)
N4	0.0570 (19)	0.0462 (18)	0.0403 (16)	−0.0087 (15)	−0.0024 (13)	−0.0240 (14)
N1	0.0447 (17)	0.057 (2)	0.0392 (16)	−0.0019 (14)	0.0025 (13)	−0.0222 (15)
C13	0.054 (2)	0.054 (2)	0.056 (2)	−0.0044 (18)	−0.0046 (17)	−0.037 (2)
C15	0.0332 (16)	0.048 (2)	0.048 (2)	−0.0018 (15)	0.0086 (14)	−0.0184 (17)
C21	0.048 (2)	0.044 (2)	0.0414 (18)	−0.0037 (16)	0.0009 (15)	−0.0192 (16)
C3	0.073 (3)	0.061 (3)	0.0342 (18)	−0.024 (2)	0.0111 (18)	−0.0161 (18)
C23	0.078 (3)	0.055 (3)	0.0374 (19)	0.002 (2)	−0.0141 (19)	−0.0172 (18)
C12	0.077 (3)	0.063 (3)	0.054 (2)	−0.021 (2)	−0.003 (2)	−0.035 (2)
C1	0.048 (2)	0.087 (4)	0.051 (2)	0.005 (2)	0.0068 (18)	−0.030 (2)
C22	0.071 (3)	0.051 (2)	0.0328 (18)	−0.007 (2)	0.0037 (17)	−0.0168 (16)
C9	0.077 (3)	0.065 (3)	0.089 (4)	0.025 (3)	−0.046 (3)	−0.049 (3)
C24	0.052 (2)	0.063 (3)	0.045 (2)	0.0123 (19)	−0.0168 (17)	−0.0246 (19)
C2	0.066 (3)	0.082 (3)	0.046 (2)	−0.012 (3)	0.020 (2)	−0.028 (2)
C11	0.105 (4)	0.097 (4)	0.082 (4)	−0.007 (4)	−0.044 (3)	−0.054 (3)
C10	0.110 (5)	0.094 (5)	0.113 (5)	0.028 (4)	−0.079 (4)	−0.053 (4)
C14	0.053 (2)	0.047 (2)	0.048 (2)	−0.0031 (17)	0.0114 (16)	−0.0272 (17)
C4	0.058 (2)	0.056 (2)	0.0307 (17)	−0.0159 (19)	−0.0017 (15)	−0.0132 (16)

Geometric parameters (Å, º) top

Zn1—N2	2.151 (3)	N1—C1	1.335 (5)
Zn1—N6	2.177 (3)	C13—C14	1.388 (6)
Zn1—N1	2.202 (3)	C13—H13	0.9300
Zn1—Br1	2.3692 (7)	C15—C14	1.376 (6)
Zn1—Br2	2.3880 (6)	C15—H15	0.9300
N5—C13	1.330 (5)	C21—C22	1.388 (6)
N5—C17	1.339 (4)	C21—H21	0.9300
N3—C7	1.330 (4)	C3—C2	1.363 (7)
N3—C18	1.339 (4)	C3—C4	1.381 (6)
C7—C6	1.403 (5)	C3—H3	0.9300
C7—C8	1.487 (5)	C23—C24	1.372 (6)
C20—N6	1.336 (4)	C23—C22	1.372 (7)
C20—C21	1.392 (5)	C23—H23	0.9300
C20—C19	1.488 (4)	C12—C11	1.357 (8)
C16—C15	1.371 (5)	C12—H12	0.9300
C16—C17	1.392 (5)	C1—C2	1.392 (6)
C16—H16	0.9300	C1—H1	0.9300
C6—N2	1.344 (4)	C22—H22	0.9300
C6—C5	1.481 (5)	C9—C10	1.394 (7)
C17—C18	1.477 (4)	C9—H9	0.9300
N6—C24	1.351 (5)	C24—H24	0.9300
N2—C19	1.341 (4)	C2—H2	0.9300
C8—N4	1.333 (5)	C11—C10	1.359 (9)
C8—C9	1.379 (6)	C11—H11	0.9300
C19—C18	1.404 (4)	C10—H10	0.9300
C5—N1	1.334 (5)	C14—H14	0.9300
C5—C4	1.382 (5)	C4—H4	0.9300
N4—C12	1.338 (5)

N2—Zn1—N6	73.75 (10)	C5—N1—Zn1	118.2 (2)
N2—Zn1—N1	72.96 (11)	C1—N1—Zn1	122.6 (3)
N6—Zn1—N1	146.71 (11)	N5—C13—C14	123.5 (4)
N2—Zn1—Br1	125.38 (8)	N5—C13—H13	118.3
N6—Zn1—Br1	102.12 (9)	C14—C13—H13	118.3
N1—Zn1—Br1	97.43 (10)	C16—C15—C14	119.5 (3)
N2—Zn1—Br2	118.61 (8)	C16—C15—H15	120.2
N6—Zn1—Br2	97.55 (9)	C14—C15—H15	120.2
N1—Zn1—Br2	97.76 (10)	C22—C21—C20	118.0 (4)
Br1—Zn1—Br2	115.93 (2)	C22—C21—H21	121.0
C13—N5—C17	117.3 (3)	C20—C21—H21	121.0
C7—N3—C18	120.4 (3)	C2—C3—C4	119.8 (4)
N3—C7—C6	119.5 (3)	C2—C3—H3	120.1
N3—C7—C8	116.7 (3)	C4—C3—H3	120.1
C6—C7—C8	123.8 (3)	C24—C23—C22	118.8 (4)
N6—C20—C21	122.2 (3)	C24—C23—H23	120.6
N6—C20—C19	114.2 (3)	C22—C23—H23	120.6
C21—C20—C19	123.5 (3)	N4—C12—C11	123.1 (4)
C15—C16—C17	118.4 (3)	N4—C12—H12	118.4
C15—C16—H16	120.8	C11—C12—H12	118.4
C17—C16—H16	120.8	N1—C1—C2	122.4 (4)
N2—C6—C7	117.2 (3)	N1—C1—H1	118.8
N2—C6—C5	114.1 (3)	C2—C1—H1	118.8
C7—C6—C5	128.7 (3)	C23—C22—C21	119.9 (4)
N5—C17—C16	123.0 (3)	C23—C22—H22	120.0
N5—C17—C18	115.8 (3)	C21—C22—H22	120.0
C16—C17—C18	120.9 (3)	C8—C9—C10	116.9 (5)
C20—N6—C24	118.6 (3)	C8—C9—H9	121.6
C20—N6—Zn1	117.8 (2)	C10—C9—H9	121.6
C24—N6—Zn1	122.1 (3)	N6—C24—C23	122.4 (4)
C19—N2—C6	121.7 (3)	N6—C24—H24	118.8
C19—N2—Zn1	118.5 (2)	C23—C24—H24	118.8
C6—N2—Zn1	119.7 (2)	C3—C2—C1	118.0 (4)
N4—C8—C9	123.8 (4)	C3—C2—H2	121.0
N4—C8—C7	114.3 (3)	C1—C2—H2	121.0
C9—C8—C7	121.9 (4)	C12—C11—C10	119.3 (4)
N2—C19—C18	117.6 (3)	C12—C11—H11	120.3
N2—C19—C20	113.7 (3)	C10—C11—H11	120.3
C18—C19—C20	128.6 (3)	C11—C10—C9	119.6 (5)
N1—C5—C4	121.3 (3)	C11—C10—H10	120.2
N1—C5—C6	114.6 (3)	C9—C10—H10	120.2
C4—C5—C6	124.1 (3)	C15—C14—C13	118.2 (3)
N3—C18—C19	118.8 (3)	C15—C14—H14	120.9
N3—C18—C17	115.5 (3)	C13—C14—H14	120.9
C19—C18—C17	125.6 (3)	C3—C4—C5	119.1 (4)
C8—N4—C12	117.2 (4)	C3—C4—H4	120.4
C5—N1—C1	119.2 (3)	C5—C4—H4	120.4

C18—N3—C7—C6	11.8 (5)	C7—C6—C5—C4	−6.9 (6)
C18—N3—C7—C8	−166.3 (3)	C7—N3—C18—C19	8.3 (5)
N3—C7—C6—N2	−20.0 (5)	C7—N3—C18—C17	−168.8 (3)
C8—C7—C6—N2	157.9 (3)	N2—C19—C18—N3	−20.2 (5)
N3—C7—C6—C5	159.1 (4)	C20—C19—C18—N3	158.3 (3)
C8—C7—C6—C5	−22.9 (6)	N2—C19—C18—C17	156.6 (3)
C13—N5—C17—C16	−1.5 (6)	C20—C19—C18—C17	−24.9 (6)
C13—N5—C17—C18	−176.1 (4)	N5—C17—C18—N3	149.6 (3)
C15—C16—C17—N5	−0.5 (6)	C16—C17—C18—N3	−25.1 (5)
C15—C16—C17—C18	173.9 (3)	N5—C17—C18—C19	−27.2 (5)
C21—C20—N6—C24	2.2 (6)	C16—C17—C18—C19	158.1 (4)
C19—C20—N6—C24	177.5 (3)	C9—C8—N4—C12	−1.2 (7)
C21—C20—N6—Zn1	−164.1 (3)	C7—C8—N4—C12	179.7 (4)
C19—C20—N6—Zn1	11.1 (4)	C4—C5—N1—C1	1.6 (6)
N2—Zn1—N6—C20	−3.2 (3)	C6—C5—N1—C1	179.8 (4)
N1—Zn1—N6—C20	−2.2 (4)	C4—C5—N1—Zn1	−176.4 (3)
Br1—Zn1—N6—C20	−126.8 (3)	C6—C5—N1—Zn1	1.9 (4)
Br2—Zn1—N6—C20	114.5 (3)	N2—Zn1—N1—C5	1.4 (3)
N2—Zn1—N6—C24	−169.0 (4)	N6—Zn1—N1—C5	0.4 (4)
N1—Zn1—N6—C24	−168.1 (3)	Br1—Zn1—N1—C5	126.2 (3)
Br1—Zn1—N6—C24	67.3 (3)	Br2—Zn1—N1—C5	−116.2 (3)
Br2—Zn1—N6—C24	−51.3 (3)	N2—Zn1—N1—C1	−176.5 (4)
C7—C6—N2—C19	7.8 (5)	N6—Zn1—N1—C1	−177.5 (4)
C5—C6—N2—C19	−171.5 (3)	Br1—Zn1—N1—C1	−51.7 (4)
C7—C6—N2—Zn1	−173.3 (2)	Br2—Zn1—N1—C1	65.9 (4)
C5—C6—N2—Zn1	7.5 (4)	C17—N5—C13—C14	2.1 (7)
N6—Zn1—N2—C19	−6.5 (3)	C17—C16—C15—C14	1.9 (6)
N1—Zn1—N2—C19	174.1 (3)	N6—C20—C21—C22	−2.2 (6)
Br1—Zn1—N2—C19	87.0 (3)	C19—C20—C21—C22	−177.1 (4)
Br2—Zn1—N2—C19	−96.3 (2)	C8—N4—C12—C11	−1.1 (7)
N6—Zn1—N2—C6	174.5 (3)	C5—N1—C1—C2	1.6 (8)
N1—Zn1—N2—C6	−4.9 (3)	Zn1—N1—C1—C2	179.5 (4)
Br1—Zn1—N2—C6	−92.0 (3)	C24—C23—C22—C21	0.5 (7)
Br2—Zn1—N2—C6	84.7 (3)	C20—C21—C22—C23	0.8 (6)
N3—C7—C8—N4	135.7 (4)	N4—C8—C9—C10	2.2 (9)
C6—C7—C8—N4	−42.3 (5)	C7—C8—C9—C10	−178.8 (6)
N3—C7—C8—C9	−43.4 (6)	C20—N6—C24—C23	−0.8 (7)
C6—C7—C8—C9	138.6 (5)	Zn1—N6—C24—C23	164.9 (4)
C6—N2—C19—C18	11.8 (5)	C22—C23—C24—N6	−0.5 (7)
Zn1—N2—C19—C18	−167.2 (2)	C4—C3—C2—C1	1.6 (8)
C6—N2—C19—C20	−167.0 (3)	N1—C1—C2—C3	−3.2 (8)
Zn1—N2—C19—C20	14.1 (4)	N4—C12—C11—C10	2.2 (10)
N6—C20—C19—N2	−16.2 (4)	C12—C11—C10—C9	−1.1 (12)
C21—C20—C19—N2	159.0 (3)	C8—C9—C10—C11	−1.0 (12)
N6—C20—C19—C18	165.2 (4)	C16—C15—C14—C13	−1.4 (6)
C21—C20—C19—C18	−19.6 (6)	N5—C13—C14—C15	−0.7 (7)
N2—C6—C5—N1	−5.9 (5)	C2—C3—C4—C5	1.3 (7)
C7—C6—C5—N1	174.9 (4)	N1—C5—C4—C3	−3.1 (6)
N2—C6—C5—C4	172.3 (4)	C6—C5—C4—C3	178.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Br2ⁱ	0.93	2.88	3.791 (7)	166

Symmetry code: (i) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[ZnBr₂(C₂₄H₁₆N₆)]
M_r	613.62
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.3985 (8), 10.5378 (8), 12.3034 (10)
α, β, γ (°)	64.898 (6), 83.187 (6), 77.901 (6)
V (Å³)	1193.05 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.40
Crystal size (mm)	0.50 × 0.40 × 0.28

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.206, 0.369
No. of measured, independent and observed [I > 2σ(I)] reflections	13823, 6412, 4954
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.126, 1.14
No. of reflections	6412
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.89, −0.91

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Zn1—N2	2.151 (3)	Zn1—Br1	2.3692 (7)
Zn1—N6	2.177 (3)	Zn1—Br2	2.3880 (6)
Zn1—N1	2.202 (3)

N2—Zn1—N6	73.75 (10)	N1—Zn1—Br1	97.43 (10)
N2—Zn1—N1	72.96 (11)	N2—Zn1—Br2	118.61 (8)
N6—Zn1—N1	146.71 (11)	N6—Zn1—Br2	97.55 (9)
N2—Zn1—Br1	125.38 (8)	N1—Zn1—Br2	97.76 (10)
N6—Zn1—Br1	102.12 (9)	Br1—Zn1—Br2	115.93 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Br2ⁱ	0.93	2.88	3.791 (7)	166

Symmetry code: (i) −x+2, −y+1, −z+2.

Acknowledgements

We are grateful to the Islamic Azad University, Shahr-e-Rey Branch, for financial support.

References

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