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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages m201-m202
https://doi.org/10.1107/S2056989015019143

Crystal structure of di­chlorido­bis­­[2-(phenyl­diazen­yl)pyridine-κN1]zinc

Luksamee Vittaya,a* Nararak Leesakul,b Saowanit Saithongb and Kittipong Chainokc

aFaculty of Science and Fisheries Technology, Rajamangala University of Technology Srivijaya, Sikao, Trang 92150, Thailand, bDepartment of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand, and cDepartment of Physics, Faculty of Science and Technology, Thammasat University, Khlong Luang, Pathum Thani 12121, Thailand
*Correspondence e-mail: nokluksamee@hotmail.com

Edited by M. Zeller, Youngstown State University, USA (Received 1 October 2015; accepted 10 October 2015; online 24 October 2015)

The structure of the title complex, [ZnCl2(C11H9N3)2], comprises two 2-(phenyl­diazen­yl)pyridine ligands coordin­ating to a central ZnII dichloride unit via the pyridyl N-atom donors, resulting in a slightly distorted tetra­hedral geometry. The complex exhibits twofold rotation symmetry, with the rotation axis bis­ecting the zinc cation. The structure is stabilized by weak inter­molecular C—H⋯Cl inter­actions [C⋯Cl = 3.411 (2) and 3.675 (2) Å], connecting neighbouring mol­ecules into layers perpendicular to the c axis.

CCDC reference: 1430587

Similar articles

1. Related literature

For background to diazenyl­pyridine compounds, see: Krause & Krause (1980[Krause, R. A. & Krause, K. (1980). Inorg. Chem. 19, 2600-2603.]). For applications of diazenyl­pyridine complexes, see: Wong & Giandomenico (1999[Wong, E. & Giandomenico, C. M. (1999). Chem. Rev. 99, 2451-2466.]); Wu et al. (2006[Wu, B.-Z., Chang, C.-C., Sree, U., Chiu, K.-H. & Lo, J.-G. (2006). Anal. Chim. Acta, 576, 91-99.]); Hotze et al. (2004[Hotze, A. C. G., Caspers, S. E., de Vos, D., Kooijman, H., Spek, A. L., Flamigni, A., Bacac, M., Sava, G., Haasnoot, J. G. & Reedijk, J. (2004). J. Biol. Inorg. Chem. 9, 354-364.]); Velders et al. (2000[Velders, A. H., Kooijman, H., Spek, A. L., Haasnoot, J. G., de Vos, D. & Reedijk, J. (2000). Inorg. Chem. 39, 2966-2967.]); Barf & Sheldon (1995[Barf, G. A. & Sheldon, R. A. (1995). J. Mol. Catal. A Chem. 98, 143-146.]). For applications of zinc–diazenyl complexes, see: Saha et al. (2014[Saha (Halder), S., Mitra, P. & Sinha, C. (2014). Polyhedron, 67, 321-328.]); Dutta et al. (2014[Dutta, P., Mallick, D., Roy, S., Torres, E.-L. & Sinha, C. (2014). Inorg. Chim. Acta, 423, 397-407.]); Datta et al. (2014[Datta, P., Mallick, D., Mondal, T.-K. & Sinha, C. (2014). Polyhedron, 71, 47-61.]); Zhang et al. (2012[Zhang, G., Wang, S., Ma, J.-S. & Yang, G. (2012). Inorg. Chim. Acta, 384, 97-104.]). For related structures, see: Leesakul et al. (2011[Leesakul, N., Pakawatchai, C., Saithong, S., Tantirungrotechai, Y. & Kwanplod, K. (2011). Acta Cryst. E67, m955-m956.]); Panneerselvam et al. (2000[Panneerselvam, K., Hansongnern, K., Rattanawit, N., Liao, F.-L. & Lu, T.-H. (2000). Anal. Sci. 16, 1107-1108.]); Steffen & Palenik (1976[Steffen, W. L. & Palenik, G. J. (1976). Acta Cryst. B32, 298-300.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [ZnCl2(C11H9N3)2]

  • Mr = 502.69

  • Orthorhombic, P b c n

  • a = 13.7960 (4) Å

  • b = 10.1905 (3) Å

  • c = 16.1305 (5) Å

  • V = 2267.76 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.34 mm−1

  • T = 298 K

  • 0.36 × 0.32 × 0.30 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.708, Tmax = 0.746

  • 65168 measured reflections

  • 2820 independent reflections

  • 2160 reflections with I > 2σ(I)

  • Rint = 0.041

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.083

  • S = 1.06

  • 2820 reflections

  • 141 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C3—H3⋯Cl1i 0.93 2.75 3.675 (2) 173
C1—H1⋯Cl1 0.93 2.81 3.411 (2) 124
Symmetry code: (i) [x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2013[Bruker (2013). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1430587

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015019143/zl2646sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019143/zl2646Isup2.hkl

checkCIF report


Comment top

Nitro­gen containing heteroaromatic systems like pyridines are some of the most investigated organic compounds primarily because of their importance in the pharmaceutical and chemical industries. Pyridine derivatives have been widely studied in analytical chemistry as an acid-base, redox and biomedical agent and for their photo-physical properties. A common synthetic pyridine derivative is 2-(phenyl­diazenyl)pyridine (Krause & Krause, 1980). This compound is a well known ligand with a basic nitro­gen atom on the pyridine ring able to coordinate to transition metal complexes. It has various applications, for example as a chemotherapeutic drug (Wong & Giandomenico, 1999), it has anti­cancer properties (Wu et al., 2006; Hotze et al., 2004; Velder et al., 2000) and is active in catalysing the epoxidation of olefins (Barf & Sheldon 1995). Coordination compounds of ZnII incorporating the diazenyl moiety were shown to have photochromic properties (Saha et al., 2014; Dutta et al., 2014; Datta et al., 2014) as well as non-linear optical properties, which were investigated for the storage of optical information (Zhang et al., 2012).

We here report the preparation and crystal structure of a new ZnII complex with the well known diazenyl­pyridine ligand 2-(phenyl­diazenyl)pyridine (C11H9N3), or azpy. The molecular structure of the title complex, [Zn(C11H9N3)2Cl2], is slightly distorted tetra­hedral as illustrated in Fig.1. The Zn atom is four coordinated by two azpy ligands via two N(pyridine) atoms [Zn1—N1 and Zn1—N1i = 2.0618 (15) Å] and two Cl- ions [Zn1—Cl1 and Zn1—Cl1i = 2.2472 (5) Å ; (i): -x+2,y,-z+3/2]. These values compare well with those of other related di­chloro ZnII compounds with pyridine ligands, such as [Zn(N,N-di­ethyl-4-[(pyridin-2-yl-kN)diazenyl]aniline)2Cl2] (Leesakul et al., 2011) with Zn—N distances of 2.0513 (9) and 2.0439 (19) Å or [Zn(pyridine)2Cl2] (Steffen & Palenik, 1976) with Zn —N distances of 2.046 (5) and 2.052 (6) Å. The reported Zn—Cl bond distances in the complex of Leesakul et al. averaged to 2.264 (6) Å, those in [Zn(pyridine)2Cl2] (Steffen & Palenik, 1976) averaged to 2.2215 Å, which are thus slightly longer and shorter respectively than those of the title complex [Zn(azpy)2Cl2].

The azo (N═N) distance in the ZnII complex is 1.244 (2) Å, which is comparable to that in the free azpy ligand, 1.248 (4) Å (Panneerselvam et al., 2000), which is expected as the azo nitro­gen of the azpy ligand is not metal coordinated. All N—Zn—Cl, Cl—Zn—Cl and N—Zn—N bond angles deviate somewhat from the ideal from 109.5°, especially for the angle N1—Zn1—N1i = 124.45 (9)°, probably due to steric demands of the azpy ligand. The torsion angle of the pyridine-azo-phenyl atoms, C5—N2—N3—C6 is 179.59 (15)°. The dihedral angle of the mean planes between the pyridine and the phenyl ring in the ligand molecule is 11.9 (1)°.

Supra­molecular features top

Weak intra and inter­molecular C—H···Cl inter­actions (C···Cl = 3.411 (2) and 3.675 (2) Å; see Table 1, Hydrogen-bond geometry) connect neighboring molecules into layers perpendicular to the c-axis (Fig. 2–4).

Experimental top

An aceto­nitrile solution (10 mL) of 2-(phenyl­diazenyl)pyridine (azpy) (0.183 g, 1.0 mmol) was added dropwise to zinc(II) chloride (0.068 g, 0.50 mmol), then refluxed for 4 h. After being filtered, the filtrate was left standing overnight at 4°C. Orange crystals were obtained (yield 71.31%, 0.179 g). Anal. Calcd for ZnC22H18N6Cl2: C, 52.56; H, 3.61; N, 16.72. Found: C, 52.56; H, 3.55; N, 16.96.

Refinement top

All H atoms of aromatic carbon were positioned geometrically and refined as riding atoms with with C—H = 0.93 Å, and with Ueq(H) = 1.2 Ueq(C).

Related literature top

For background to diazenylpyridine compounds, see: Krause & Krause (1980). For applications of diazenylpyridine complexes, see: Wong & Giandomenico (1999); Wu et al. (2006); Hotze et al. (2004); Velder et al. (2000); Barf & Sheldon (1995). For applications of zinc–diazenyl complexes, see: Saha et al. (2014); Dutta et al. (2014); Datta et al. (2014); Zhang et al. (2012). For related structures, see: Leesakul et al. (2011), Panneerselvam et al. (2000), and Steffen & Palenik (1976).

Structure description top

Nitro­gen containing heteroaromatic systems like pyridines are some of the most investigated organic compounds primarily because of their importance in the pharmaceutical and chemical industries. Pyridine derivatives have been widely studied in analytical chemistry as an acid-base, redox and biomedical agent and for their photo-physical properties. A common synthetic pyridine derivative is 2-(phenyl­diazenyl)pyridine (Krause & Krause, 1980). This compound is a well known ligand with a basic nitro­gen atom on the pyridine ring able to coordinate to transition metal complexes. It has various applications, for example as a chemotherapeutic drug (Wong & Giandomenico, 1999), it has anti­cancer properties (Wu et al., 2006; Hotze et al., 2004; Velder et al., 2000) and is active in catalysing the epoxidation of olefins (Barf & Sheldon 1995). Coordination compounds of ZnII incorporating the diazenyl moiety were shown to have photochromic properties (Saha et al., 2014; Dutta et al., 2014; Datta et al., 2014) as well as non-linear optical properties, which were investigated for the storage of optical information (Zhang et al., 2012).

We here report the preparation and crystal structure of a new ZnII complex with the well known diazenyl­pyridine ligand 2-(phenyl­diazenyl)pyridine (C11H9N3), or azpy. The molecular structure of the title complex, [Zn(C11H9N3)2Cl2], is slightly distorted tetra­hedral as illustrated in Fig.1. The Zn atom is four coordinated by two azpy ligands via two N(pyridine) atoms [Zn1—N1 and Zn1—N1i = 2.0618 (15) Å] and two Cl- ions [Zn1—Cl1 and Zn1—Cl1i = 2.2472 (5) Å ; (i): -x+2,y,-z+3/2]. These values compare well with those of other related di­chloro ZnII compounds with pyridine ligands, such as [Zn(N,N-di­ethyl-4-[(pyridin-2-yl-kN)diazenyl]aniline)2Cl2] (Leesakul et al., 2011) with Zn—N distances of 2.0513 (9) and 2.0439 (19) Å or [Zn(pyridine)2Cl2] (Steffen & Palenik, 1976) with Zn —N distances of 2.046 (5) and 2.052 (6) Å. The reported Zn—Cl bond distances in the complex of Leesakul et al. averaged to 2.264 (6) Å, those in [Zn(pyridine)2Cl2] (Steffen & Palenik, 1976) averaged to 2.2215 Å, which are thus slightly longer and shorter respectively than those of the title complex [Zn(azpy)2Cl2].

The azo (N═N) distance in the ZnII complex is 1.244 (2) Å, which is comparable to that in the free azpy ligand, 1.248 (4) Å (Panneerselvam et al., 2000), which is expected as the azo nitro­gen of the azpy ligand is not metal coordinated. All N—Zn—Cl, Cl—Zn—Cl and N—Zn—N bond angles deviate somewhat from the ideal from 109.5°, especially for the angle N1—Zn1—N1i = 124.45 (9)°, probably due to steric demands of the azpy ligand. The torsion angle of the pyridine-azo-phenyl atoms, C5—N2—N3—C6 is 179.59 (15)°. The dihedral angle of the mean planes between the pyridine and the phenyl ring in the ligand molecule is 11.9 (1)°.

Weak intra and inter­molecular C—H···Cl inter­actions (C···Cl = 3.411 (2) and 3.675 (2) Å; see Table 1, Hydrogen-bond geometry) connect neighboring molecules into layers perpendicular to the c-axis (Fig. 2–4).

An aceto­nitrile solution (10 mL) of 2-(phenyl­diazenyl)pyridine (azpy) (0.183 g, 1.0 mmol) was added dropwise to zinc(II) chloride (0.068 g, 0.50 mmol), then refluxed for 4 h. After being filtered, the filtrate was left standing overnight at 4°C. Orange crystals were obtained (yield 71.31%, 0.179 g). Anal. Calcd for ZnC22H18N6Cl2: C, 52.56; H, 3.61; N, 16.72. Found: C, 52.56; H, 3.55; N, 16.96.

For background to diazenylpyridine compounds, see: Krause & Krause (1980). For applications of diazenylpyridine complexes, see: Wong & Giandomenico (1999); Wu et al. (2006); Hotze et al. (2004); Velder et al. (2000); Barf & Sheldon (1995). For applications of zinc–diazenyl complexes, see: Saha et al. (2014); Dutta et al. (2014); Datta et al. (2014); Zhang et al. (2012). For related structures, see: Leesakul et al. (2011), Panneerselvam et al. (2000), and Steffen & Palenik (1976).

Refinement details top

All H atoms of aromatic carbon were positioned geometrically and refined as riding atoms with with C—H = 0.93 Å, and with Ueq(H) = 1.2 Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of [Zn(C11H9N3)2Cl2] with thermal ellipsoids plotted at the 30% probability level. Non-labelled atoms are created by the twofold symmetry axis [symmetry operator: (i) -x + 2, y, -z + 3/2].
[Figure 2] Fig. 2. Two–dimensional interaction sheet of [Zn(C11H9N3)2Cl2] plotted down c, formed through weak C–H···Cl interactions.
[Figure 3] Fig. 3. Two–dimensional interaction sheet of [Zn(C11H9N3)2Cl2] plotted down b axis, formed through weak C–H···Cl interactions.
[Figure 4] Fig. 4. The arrangement of two-dimensional layers plotted down the a axis showing a lateral view of alternating C···Cl contact directions of adjacent sheets (A and B layers). H atoms are omitted for clarity.
Dichloridobis[2-(phenyldiazenyl)pyridine-κN1]zinc top
Crystal data top
[ZnCl2(C11H9N3)2]Dx = 1.472 Mg m−3
Mr = 502.69Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 9900 reflections
a = 13.7960 (4) Åθ = 3.2–28.2°
b = 10.1905 (3) ŵ = 1.34 mm−1
c = 16.1305 (5) ÅT = 298 K
V = 2267.76 (12) Å3Block, orange
Z = 40.36 × 0.32 × 0.30 mm
F(000) = 1024
Data collection top
Bruker APEXII CCD
diffractometer		2160 reflections with I > 2σ(I)
φ and ω scansRint = 0.041
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		θmax = 28.3°, θmin = 3.5°
Tmin = 0.708, Tmax = 0.746h = −18→18
65168 measured reflectionsk = −13→13
2820 independent reflectionsl = −21→21
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0384P)2 + 0.7794P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2820 reflectionsΔρmax = 0.35 e Å−3
141 parametersΔρmin = −0.22 e Å−3
Crystal data top
[ZnCl2(C11H9N3)2]V = 2267.76 (12) Å3
Mr = 502.69Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 13.7960 (4) ŵ = 1.34 mm−1
b = 10.1905 (3) ÅT = 298 K
c = 16.1305 (5) Å0.36 × 0.32 × 0.30 mm
Data collection top
Bruker APEXII CCD
diffractometer		2820 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		2160 reflections with I > 2σ(I)
Tmin = 0.708, Tmax = 0.746Rint = 0.041
65168 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.083H-atom parameters constrained
S = 1.06Δρmax = 0.35 e Å−3
2820 reflectionsΔρmin = −0.22 e Å−3
141 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn11.00000.21091 (3)0.75000.04573 (11)
Cl10.96785 (4)0.08709 (5)0.63805 (3)0.06114 (15)
N10.86977 (11)0.30520 (15)0.76959 (10)0.0468 (3)
N20.95560 (12)0.45206 (15)0.84789 (10)0.0514 (4)
N30.95301 (13)0.55766 (16)0.88646 (11)0.0584 (4)
C10.78854 (15)0.2566 (2)0.73676 (13)0.0571 (5)
H10.79270.18320.70260.069*
C20.69884 (17)0.3110 (2)0.75155 (14)0.0676 (6)
H20.64340.27550.72750.081*
C30.69288 (16)0.4185 (2)0.80247 (16)0.0730 (6)
H30.63300.45630.81400.088*
C40.77541 (15)0.4698 (2)0.83614 (14)0.0627 (5)
H40.77260.54290.87060.075*
C50.86318 (13)0.41115 (18)0.81815 (11)0.0484 (4)
C61.04406 (15)0.60029 (19)0.91730 (12)0.0555 (5)
C71.04401 (19)0.7222 (2)0.95484 (16)0.0696 (6)
H70.98660.76960.95930.084*
C81.1291 (2)0.7733 (3)0.98561 (16)0.0789 (7)
H81.12930.85531.01100.095*
C91.2132 (2)0.7037 (3)0.97888 (15)0.0763 (7)
H91.27070.73900.99900.092*
C101.21338 (17)0.5810 (2)0.94239 (14)0.0706 (6)
H101.27090.53380.93860.085*
C111.12915 (16)0.5283 (2)0.91168 (13)0.0623 (5)
H111.12910.44550.88740.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03382 (16)0.04842 (18)0.05494 (19)0.0000.00041 (11)0.000
Cl10.0475 (3)0.0725 (3)0.0635 (3)0.0004 (2)−0.0018 (2)−0.0153 (2)
N10.0390 (8)0.0491 (8)0.0522 (8)0.0044 (6)0.0020 (6)0.0048 (6)
N20.0533 (9)0.0493 (8)0.0518 (9)0.0059 (7)0.0038 (7)0.0004 (7)
N30.0597 (11)0.0517 (9)0.0638 (10)0.0067 (8)0.0061 (8)−0.0026 (8)
C10.0431 (10)0.0613 (11)0.0669 (13)0.0021 (9)−0.0025 (8)0.0013 (9)
C20.0393 (10)0.0797 (15)0.0837 (16)0.0077 (10)−0.0056 (10)0.0097 (12)
C30.0490 (12)0.0840 (16)0.0861 (16)0.0254 (11)0.0070 (11)0.0133 (13)
C40.0602 (12)0.0615 (12)0.0663 (12)0.0211 (10)0.0057 (10)0.0027 (10)
C50.0472 (10)0.0497 (10)0.0483 (10)0.0089 (8)0.0034 (8)0.0093 (8)
C60.0584 (12)0.0551 (11)0.0530 (11)0.0001 (9)0.0074 (9)0.0013 (9)
C70.0696 (14)0.0602 (13)0.0790 (15)0.0002 (10)0.0151 (12)−0.0122 (11)
C80.0851 (18)0.0683 (15)0.0832 (16)−0.0170 (13)0.0133 (14)−0.0153 (12)
C90.0742 (16)0.0856 (17)0.0690 (14)−0.0211 (13)0.0029 (12)0.0037 (12)
C100.0624 (13)0.0789 (16)0.0704 (14)0.0030 (11)0.0025 (11)0.0065 (12)
C110.0657 (13)0.0609 (12)0.0602 (12)0.0051 (10)0.0035 (10)−0.0020 (10)
Geometric parameters (Å, º) top
Zn1—N12.0618 (15)C3—H30.9300
Zn1—N1i2.0619 (15)C4—C51.381 (3)
Zn1—Cl1i2.2471 (5)C4—H40.9300
Zn1—Cl12.2472 (5)C6—C71.382 (3)
N1—C11.335 (3)C6—C111.387 (3)
N1—C51.337 (2)C7—C81.377 (3)
N2—N31.244 (2)C7—H70.9300
N2—C51.425 (2)C8—C91.364 (4)
N3—C61.419 (3)C8—H80.9300
C1—C21.377 (3)C9—C101.382 (3)
C1—H10.9300C9—H90.9300
C2—C31.372 (3)C10—C111.372 (3)
C2—H20.9300C10—H100.9300
C3—C41.365 (3)C11—H110.9300
N1—Zn1—N1i124.45 (9)C5—C4—H4120.6
N1—Zn1—Cl1i108.09 (4)N1—C5—C4122.15 (19)
N1i—Zn1—Cl1i102.29 (5)N1—C5—N2111.89 (15)
N1—Zn1—Cl1102.29 (5)C4—C5—N2125.96 (18)
N1i—Zn1—Cl1108.09 (4)C7—C6—C11120.3 (2)
Cl1i—Zn1—Cl1111.68 (3)C7—C6—N3115.36 (19)
C1—N1—C5118.37 (17)C11—C6—N3124.36 (19)
C1—N1—Zn1119.85 (13)C8—C7—C6119.8 (2)
C5—N1—Zn1121.69 (13)C8—C7—H7120.1
N3—N2—C5113.33 (16)C6—C7—H7120.1
N2—N3—C6114.51 (17)C9—C8—C7120.0 (2)
N1—C1—C2122.4 (2)C9—C8—H8120.0
N1—C1—H1118.8C7—C8—H8120.0
C2—C1—H1118.8C8—C9—C10120.4 (2)
C3—C2—C1118.6 (2)C8—C9—H9119.8
C3—C2—H2120.7C10—C9—H9119.8
C1—C2—H2120.7C11—C10—C9120.4 (2)
C4—C3—C2119.6 (2)C11—C10—H10119.8
C4—C3—H3120.2C9—C10—H10119.8
C2—C3—H3120.2C10—C11—C6119.1 (2)
C3—C4—C5118.8 (2)C10—C11—H11120.5
C3—C4—H4120.6C6—C11—H11120.5
C5—N2—N3—C6179.59 (15)N3—N2—C5—N1173.32 (16)
C5—N1—C1—C2−0.4 (3)N3—N2—C5—C4−7.2 (3)
Zn1—N1—C1—C2176.25 (16)N2—N3—C6—C7175.28 (19)
N1—C1—C2—C3−0.5 (3)N2—N3—C6—C11−4.7 (3)
C1—C2—C3—C40.9 (3)C11—C6—C7—C81.0 (3)
C2—C3—C4—C5−0.3 (3)N3—C6—C7—C8−179.0 (2)
C1—N1—C5—C41.0 (3)C6—C7—C8—C90.1 (4)
Zn1—N1—C5—C4−175.57 (14)C7—C8—C9—C10−1.0 (4)
C1—N1—C5—N2−179.50 (16)C8—C9—C10—C110.7 (4)
Zn1—N1—C5—N23.9 (2)C9—C10—C11—C60.4 (3)
C3—C4—C5—N1−0.7 (3)C7—C6—C11—C10−1.3 (3)
C3—C4—C5—N2179.92 (19)N3—C6—C11—C10178.7 (2)
Symmetry code: (i) −x+2, y, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cl1ii0.932.753.675 (2)173
C1—H1···Cl10.932.813.411 (2)124
Symmetry code: (ii) x−1/2, y+1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cl1i0.932.753.675 (2)172.9
C1—H1···Cl10.932.813.411 (2)123.6
Symmetry code: (i) x−1/2, y+1/2, −z+3/2.
 

Acknowledgements

We are grateful to the Faculty of Science and Fisheries Technology, Rajamangala University of Technology Srivijaya, for financial support and to the Center for Innovation in Chemistry (PERCH–CIC) Comission on Higher Education, Ministry of Education, Thailand, for partial support. We are also grateful for support with facilities from the Department of Chemistry, Faculty of Science, Prince of Songkla University. We express our acknowledgements to Dr Brian Hodgson, Faculty of Pharmaceutical Science, Prince of Songkla University, for reading the manuscript and providing comments.

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ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages m201-m202
https://doi.org/10.1107/S2056989015019143
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