(2-{[2-(1H-Benzimidazol-2-yl-κN3)phen­yl]imino­methyl-κN}-5-methyl­phenolato-κO)chloridozinc(II)

Eltayeb, N.E.; Teoh, S.G.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536811030170

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages m1182-m1183

doi:10.1107/S1600536811030170

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(2-{[2-(1H-Benzimidazol-2-yl-κN³)phenyl]iminomethyl-κN}-5-methylphenolato-κO)chloridozinc(II)

Naser Eltaher Eltayeb,^a,^b Siang Guan Teoh,^a Suchada Chantrapromma ^c ‡ and Hoong-Kun Fun ^d ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Pure and Applied Sciences, International University of Africa, Sudan, ^cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 17 July 2011; accepted 26 July 2011; online 2 August 2011)

In the title mononuclear complex, [Zn(C₂₁H₁₆N₃O)Cl], the Zn^II ion is coordinated in a distorted tetrahedral geometry by two benzimidazole N atoms and one phenolate O atom from the tridentate Schiff base ligand and a chloride ligand. The benzimidazole ring system forms dihedral angles of 26.68 (9) and 56.16 (9)° with the adjacent benzene ring and the methylphenolate group benzene ring, respectively. In the crystal, molecules are linked by N—H⋯Cl hydrogen bonds into chains along [100]. Furthermore, weak C—H⋯O and C—H⋯π interactions, in addition to π–π interactions with centroid–centroid distances in the range 3.5826 (13)–3.9681 (13) Å, are also observed.

Related literature

For standard bond-length data, see: Allen et al. (1987 ). For background to benzimidazoles and their applications, see: Chassaing et al. (2008 ); Kucukbay et al. (2003 ); Podunavac-Kuzmanovic & Cvetkovic (2010 ); Podunavac-Kuzmanovic et al. (1999 ); Podunavac-Kuzmanovic & Markov (2006 ); Xue et al. (2011 ). For related structures, see: Eltayeb et al. (2007 , 2009 ); Eltayeb, Teoh, Chantrapromma & Fun (2011 ); Eltayeb, Teoh, Yeap & Fun (2011 ); Maldonado-Rogado et al. (2007 ); Tong & Ye (2004 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ).

Experimental

Crystal data

[Zn(C₂₁H₁₆N₃O)Cl]
M_r = 427.21
Monoclinic, P 2₁ /c
a = 8.6338 (1) Å
b = 19.4952 (2) Å
c = 10.9687 (1) Å
β = 99.675 (1)°
V = 1819.97 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.51 mm⁻¹
T = 100 K
0.26 × 0.18 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.694, T_max = 0.878
22729 measured reflections
5678 independent reflections
3773 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.088
S = 1.03
5678 reflections
249 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C15–C20 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N1⋯Cl1ⁱ	0.75 (3)	2.53 (3)	3.2352 (19)	157 (2)
C2—H2A⋯O1ⁱⁱ	0.93	2.59	3.425 (3)	149
C12—H12A⋯Cg1ⁱⁱⁱ	0.93	2.96	3.762 (3)	145
C21—H21C⋯Cg2^iv	0.96	2.92	3.741 (3)	144
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+1; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811030170/lh6598sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811030170/lh6598Isup2.hkl

checkCIF report

Comment top

Benzimidazole compounds and their complexes have been found to show diverse biological activity (Chassaing et al., 2008; Kucukbay et al., 2003; Podunavac-Kuzmanovic & Cvetkovic, 2010; Podunavac-Kuzmanovic et al., 1999; Podunavac-Kuzmanovic & Markov, 2006) including inhibition against enteroviruses (Xue et al., 2011). Our ongoing structural studies involves benzimidazoles (Eltayeb et al., 2007, 2009; Eltayeb, Teoh, Yeap & Fun, 2011) and their complexes (Eltayeb, Teoh, Chantrapromma & Fun, 2011). In the preparation of the title complex (I), 2-(2-aminophenyl)-1H-benzimidazole undergoes a condensation reaction with 2-hydroxy-4-methylbenzaldehyde to give a Schiff base ligand and forming the zinc(II) complex.

Complex (I) is a mononuclear zinc(II) complex (Fig. 1) in which the environment around the Zn^II ion is a distorted tetrahedral geometry and the Zn^II ion is four-coordinated by the two benzimidazole N atoms, one phenolate O atom and a Cl ligand. In the complex, the Schiff base ligand acts as a tridentate ligand. The bond angles around the central metal zinc(II) show large deviations from ideal tetrahedral geometry [O1-Zn1-Cl1 = 115.14 (5)°, N1-Zn1-Cl1 = 111.84 (5)°, N3-Zn1-Cl1 = 120.39 (6)°; and the bite angles N1–Zn1-N3 = 90.39 (7)° and O1-Zn1-N3 = 95.00 (7)°]. The Zn-N [1.9954 (17) and 2.2092 (18) Å], Zn-O [1.9137 (15) Å] and Zn-Cl [2.2249 (7) Å] bond lengths are comparable to those of similar Zn(II) benzimidazole complexes (Eltayeb, Teoh, Chantrapromma & Fun, 2011; Maldonado-Rogado et al., 2007; Tong & Ye, 2004). The benzimidazole ring system (C1–C7/N1–N2) is planar with an r.m.s. deviation of 0.0074 (2) Å and the largest deviation of 0.029 (2) Å for atom N1. The benzimidazole ring system forms dihedral angles of 26.68 (9) and 56.16 (9)° with the C8–C13 and C15–C20 rings, respectively. The dihedral angle between the C8–C13 and C15–C20 benzene rings is 35.26 (11)°. The bond lengths of ligand are within normal ranges (Allen et al., 1987).

In the crystal structure of (I) as shown Fig. 2, the molecules are linked through N—H···Cl hydrogen bonds (Table 1) into chains along the a axis. C—H···O and C—H···π weak interactions (Table 1) are also present. π–π interactions were also observed with centroid···centroid distances: Cg1···Cg2^v = 3.6134 (13) Å; Cg1···Cg3^vi = 3.9681 (13) Å and Cg2···Cg2^v = 3.5826 (13) Å; Cg1, Cg2 and Cg3 are the centroids of the C1/C6–C7/N1–N2, C1–C6 and C8–C13 rings, respectively [symmetry codes: (v) 2-x, -x, 1-z; (vi) 2-x, -y, 2-z].

Related literature top

For standard bond-length data, see: Allen et al. (1987). For background to benzimidazoles and their applications, see: Chassaing et al. (2008); Kucukbay et al. (2003); Podunavac-Kuzmanovic & Cvetkovic (2010); Podunavac-Kuzmanovic et al. (1999); Podunavac-Kuzmanovic & Markov (2006); Xue et al. (2011). For related structures, see: Eltayeb et al. (2007, 2009); Eltayeb, Teoh, Chantrapromma & Fun (2011); Eltayeb, Teoh, Yeap & Fun (2011); Maldonado-Rogado et al. (2007); Tong & Ye (2004). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986).

Experimental top

The title compound was synthesized by adding 2-hydroxy-4-methylbenzaldehyde (0.136 g, 1.0 mmol) to a solution of 2-(2-aminophenyl)-1H-benzimidazole (0.209 g, 1.0 mmol) in ethanol (30 mL). The color of the resulting solution was pale-yellow. Upon adding zinc chloride (0.136 g, 1.0 mmol), the color of the solution turned golden-yellow. The mixture was refluxed with stirring for 3 hrs. Yellow block-shaped single crystals of the title compound suitable for x-ray structure determination were obtained from ethanol by slow evaporation at room temperature after several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound viewed approximately along the c axis. N—H···Cl hydrogen bonds are shown as dashed lines.

(2-{[2-(1H-Benzimidazol-2-yl-κN³)phenyl]iminomethyl- κN}-5-methylphenolato-κO)chloridozinc(II) top

Crystal data top

[Zn(C₂₁H₁₆N₃O)Cl]	F(000) = 872
M_r = 427.21	D_x = 1.559 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5678 reflections
a = 8.6338 (1) Å	θ = 2.1–30.7°
b = 19.4952 (2) Å	µ = 1.51 mm⁻¹
c = 10.9687 (1) Å	T = 100 K
β = 99.675 (1)°	Block, yellow
V = 1819.97 (3) Å³	0.26 × 0.18 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	5678 independent reflections
Radiation source: sealed tube	3773 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 30.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
T_min = 0.694, T_max = 0.878	k = −28→26
22729 measured reflections	l = −12→15

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0283P)² + 0.6885P] where P = (F_o² + 2F_c²)/3
5678 reflections	(Δ/σ)_max = 0.001
249 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Zn(C₂₁H₁₆N₃O)Cl]	V = 1819.97 (3) Å³
M_r = 427.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6338 (1) Å	µ = 1.51 mm⁻¹
b = 19.4952 (2) Å	T = 100 K
c = 10.9687 (1) Å	0.26 × 0.18 × 0.09 mm
β = 99.675 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5678 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3773 reflections with I > 2σ(I)
T_min = 0.694, T_max = 0.878	R_int = 0.042
22729 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.64 e Å⁻³
5678 reflections	Δρ_min = −0.39 e Å⁻³
249 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.66403 (3)	0.062335 (13)	0.71581 (2)	0.03608 (9)
Cl1	0.50460 (7)	0.00213 (4)	0.81468 (7)	0.05647 (19)
O1	0.56252 (18)	0.11090 (8)	0.57283 (14)	0.0414 (4)
N1	0.86821 (19)	0.01439 (9)	0.71573 (16)	0.0330 (4)
N2	1.1246 (2)	−0.00194 (10)	0.76330 (18)	0.0375 (4)
N3	0.7792 (2)	0.14557 (9)	0.79697 (16)	0.0349 (4)
C1	0.9123 (2)	−0.03570 (11)	0.63665 (19)	0.0336 (5)
C2	0.8211 (3)	−0.07198 (12)	0.5421 (2)	0.0413 (5)
H2A	0.7133	−0.0651	0.5221	0.050*
C3	0.8977 (3)	−0.11859 (13)	0.4794 (2)	0.0504 (6)
H3A	0.8401	−0.1447	0.4167	0.060*
C4	1.0616 (3)	−0.12755 (13)	0.5080 (2)	0.0496 (6)
H4A	1.1098	−0.1590	0.4628	0.060*
C5	1.1522 (3)	−0.09105 (12)	0.6007 (2)	0.0445 (6)
H5A	1.2606	−0.0967	0.6190	0.053*
C6	1.0740 (3)	−0.04558 (11)	0.6655 (2)	0.0358 (5)
C7	0.9989 (2)	0.03287 (11)	0.79017 (19)	0.0318 (5)
C8	1.0111 (2)	0.08132 (11)	0.89379 (19)	0.0332 (5)
C9	1.1357 (3)	0.07388 (12)	0.9935 (2)	0.0388 (5)
H9A	1.2078	0.0386	0.9919	0.047*
C10	1.1532 (3)	0.11775 (13)	1.0936 (2)	0.0456 (6)
H10A	1.2370	0.1123	1.1582	0.055*
C11	1.0461 (3)	0.16957 (14)	1.0971 (2)	0.0520 (7)
H11A	1.0567	0.1986	1.1653	0.062*
C12	0.9230 (3)	0.17893 (13)	1.0006 (2)	0.0451 (6)
H12A	0.8517	0.2144	1.0042	0.054*
C13	0.9045 (2)	0.13597 (11)	0.89831 (19)	0.0351 (5)
C14	0.7407 (2)	0.20702 (12)	0.7581 (2)	0.0374 (5)
H14A	0.7912	0.2430	0.8042	0.045*
C15	0.6287 (2)	0.22529 (11)	0.6517 (2)	0.0362 (5)
C16	0.6017 (3)	0.29611 (12)	0.6307 (2)	0.0438 (6)
H16A	0.6503	0.3273	0.6890	0.053*
C17	0.5065 (3)	0.32035 (13)	0.5274 (2)	0.0470 (6)
H17A	0.4893	0.3673	0.5172	0.056*
C18	0.4349 (3)	0.27452 (12)	0.4370 (2)	0.0411 (5)
C19	0.4615 (3)	0.20532 (12)	0.4549 (2)	0.0408 (5)
H19A	0.4170	0.1753	0.3928	0.049*
C20	0.5529 (2)	0.17729 (12)	0.5628 (2)	0.0365 (5)
C21	0.3284 (3)	0.29989 (14)	0.3235 (2)	0.0541 (7)
H21A	0.3299	0.2681	0.2569	0.081*
H21B	0.3640	0.3440	0.3006	0.081*
H21C	0.2232	0.3038	0.3405	0.081*
H1N1	1.208 (3)	0.0047 (13)	0.793 (2)	0.051 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02462 (12)	0.03720 (15)	0.04474 (16)	0.00021 (11)	0.00096 (10)	0.00267 (12)
Cl1	0.0295 (3)	0.0641 (4)	0.0770 (5)	−0.0005 (3)	0.0123 (3)	0.0210 (4)
O1	0.0393 (8)	0.0357 (9)	0.0447 (9)	−0.0003 (7)	−0.0063 (7)	0.0032 (7)
N1	0.0269 (8)	0.0347 (10)	0.0367 (9)	−0.0008 (7)	0.0029 (7)	0.0039 (8)
N2	0.0252 (9)	0.0420 (11)	0.0433 (11)	0.0027 (9)	0.0000 (8)	0.0006 (9)
N3	0.0280 (8)	0.0382 (10)	0.0372 (10)	0.0010 (8)	0.0018 (7)	−0.0020 (8)
C1	0.0344 (11)	0.0308 (11)	0.0357 (11)	0.0002 (9)	0.0062 (9)	0.0037 (9)
C2	0.0374 (12)	0.0410 (14)	0.0442 (13)	−0.0029 (10)	0.0030 (10)	0.0003 (11)
C3	0.0646 (17)	0.0414 (14)	0.0440 (14)	−0.0089 (13)	0.0054 (12)	−0.0046 (12)
C4	0.0651 (17)	0.0369 (14)	0.0507 (15)	0.0040 (12)	0.0211 (13)	−0.0006 (11)
C5	0.0437 (13)	0.0407 (13)	0.0505 (14)	0.0077 (11)	0.0118 (11)	0.0068 (12)
C6	0.0337 (11)	0.0356 (12)	0.0388 (12)	0.0015 (9)	0.0079 (9)	0.0054 (10)
C7	0.0262 (9)	0.0350 (11)	0.0340 (11)	0.0007 (9)	0.0043 (8)	0.0070 (9)
C8	0.0288 (10)	0.0352 (12)	0.0356 (11)	−0.0040 (9)	0.0055 (8)	0.0050 (9)
C9	0.0322 (11)	0.0425 (13)	0.0401 (12)	−0.0009 (10)	0.0014 (9)	0.0066 (10)
C10	0.0396 (12)	0.0573 (16)	0.0365 (12)	−0.0095 (12)	−0.0038 (10)	0.0043 (11)
C11	0.0538 (15)	0.0623 (17)	0.0377 (13)	−0.0100 (14)	0.0017 (11)	−0.0110 (12)
C12	0.0430 (13)	0.0491 (15)	0.0429 (13)	0.0009 (11)	0.0061 (10)	−0.0089 (11)
C13	0.0281 (10)	0.0392 (12)	0.0367 (11)	−0.0046 (9)	0.0021 (8)	0.0006 (10)
C14	0.0331 (11)	0.0389 (13)	0.0400 (12)	0.0001 (10)	0.0060 (9)	−0.0046 (10)
C15	0.0327 (11)	0.0366 (12)	0.0398 (12)	0.0038 (9)	0.0075 (9)	0.0011 (10)
C16	0.0417 (13)	0.0394 (13)	0.0497 (14)	0.0029 (11)	0.0056 (11)	−0.0042 (11)
C17	0.0442 (13)	0.0387 (14)	0.0581 (15)	0.0063 (11)	0.0084 (12)	0.0055 (12)
C18	0.0344 (11)	0.0458 (14)	0.0440 (13)	0.0070 (10)	0.0089 (10)	0.0078 (11)
C19	0.0370 (12)	0.0460 (14)	0.0385 (12)	−0.0024 (10)	0.0036 (9)	−0.0001 (10)
C20	0.0272 (10)	0.0426 (13)	0.0402 (12)	0.0003 (9)	0.0070 (9)	−0.0010 (10)
C21	0.0474 (14)	0.0585 (17)	0.0544 (15)	0.0114 (13)	0.0022 (12)	0.0111 (13)

Geometric parameters (Å, º) top

Zn1—O1	1.9137 (15)	C8—C13	1.415 (3)
Zn1—N1	1.9954 (17)	C9—C10	1.380 (3)
Zn1—N3	2.0292 (18)	C9—H9A	0.9300
Zn1—Cl1	2.2249 (7)	C10—C11	1.375 (3)
O1—C20	1.300 (3)	C10—H10A	0.9300
N1—C7	1.327 (2)	C11—C12	1.380 (3)
N1—C1	1.401 (3)	C11—H11A	0.9300
N2—C7	1.354 (3)	C12—C13	1.388 (3)
N2—C6	1.381 (3)	C12—H12A	0.9300
N2—H1N1	0.75 (3)	C14—C15	1.430 (3)
N3—C14	1.296 (3)	C14—H14A	0.9300
N3—C13	1.427 (2)	C15—C16	1.413 (3)
C1—C2	1.386 (3)	C15—C20	1.428 (3)
C1—C6	1.392 (3)	C16—C17	1.367 (3)
C2—C3	1.375 (3)	C16—H16A	0.9300
C2—H2A	0.9300	C17—C18	1.399 (3)
C3—C4	1.408 (4)	C17—H17A	0.9300
C3—H3A	0.9300	C18—C19	1.377 (3)
C4—C5	1.373 (3)	C18—C21	1.501 (3)
C4—H4A	0.9300	C19—C20	1.417 (3)
C5—C6	1.381 (3)	C19—H19A	0.9300
C5—H5A	0.9300	C21—H21A	0.9600
C7—C8	1.468 (3)	C21—H21B	0.9600
C8—C9	1.406 (3)	C21—H21C	0.9600

O1—Zn1—N1	120.95 (7)	C10—C9—H9A	119.3
O1—Zn1—N3	95.00 (7)	C8—C9—H9A	119.3
N1—Zn1—N3	90.39 (7)	C11—C10—C9	119.6 (2)
O1—Zn1—Cl1	115.14 (5)	C11—C10—H10A	120.2
N1—Zn1—Cl1	111.84 (5)	C9—C10—H10A	120.2
N3—Zn1—Cl1	120.39 (6)	C10—C11—C12	120.7 (2)
C20—O1—Zn1	125.15 (14)	C10—C11—H11A	119.7
C7—N1—C1	106.20 (17)	C12—C11—H11A	119.7
C7—N1—Zn1	122.18 (15)	C11—C12—C13	120.6 (2)
C1—N1—Zn1	131.21 (13)	C11—C12—H12A	119.7
C7—N2—C6	108.47 (18)	C13—C12—H12A	119.7
C7—N2—H1N1	124 (2)	C12—C13—C8	119.72 (19)
C6—N2—H1N1	127 (2)	C12—C13—N3	121.3 (2)
C14—N3—C13	119.79 (18)	C8—C13—N3	118.95 (19)
C14—N3—Zn1	120.98 (14)	N3—C14—C15	126.9 (2)
C13—N3—Zn1	119.23 (14)	N3—C14—H14A	116.6
C2—C1—C6	121.4 (2)	C15—C14—H14A	116.6
C2—C1—N1	129.8 (2)	C16—C15—C20	119.0 (2)
C6—C1—N1	108.80 (18)	C16—C15—C14	116.5 (2)
C3—C2—C1	116.9 (2)	C20—C15—C14	124.3 (2)
C3—C2—H2A	121.6	C17—C16—C15	122.2 (2)
C1—C2—H2A	121.6	C17—C16—H16A	118.9
C2—C3—C4	121.4 (2)	C15—C16—H16A	118.9
C2—C3—H3A	119.3	C16—C17—C18	119.9 (2)
C4—C3—H3A	119.3	C16—C17—H17A	120.0
C5—C4—C3	121.8 (2)	C18—C17—H17A	120.0
C5—C4—H4A	119.1	C19—C18—C17	118.8 (2)
C3—C4—H4A	119.1	C19—C18—C21	120.3 (2)
C4—C5—C6	116.5 (2)	C17—C18—C21	120.9 (2)
C4—C5—H5A	121.7	C18—C19—C20	123.6 (2)
C6—C5—H5A	121.7	C18—C19—H19A	118.2
C5—C6—N2	132.6 (2)	C20—C19—H19A	118.2
C5—C6—C1	122.0 (2)	O1—C20—C19	118.2 (2)
N2—C6—C1	105.41 (19)	O1—C20—C15	125.38 (19)
N1—C7—N2	111.11 (19)	C19—C20—C15	116.4 (2)
N1—C7—C8	126.48 (19)	C18—C21—H21A	109.5
N2—C7—C8	122.33 (18)	C18—C21—H21B	109.5
C9—C8—C13	117.9 (2)	H21A—C21—H21B	109.5
C9—C8—C7	118.8 (2)	C18—C21—H21C	109.5
C13—C8—C7	123.31 (18)	H21A—C21—H21C	109.5
C10—C9—C8	121.5 (2)	H21B—C21—H21C	109.5

N1—Zn1—O1—C20	−107.74 (18)	N1—C7—C8—C9	152.4 (2)
N3—Zn1—O1—C20	−14.28 (18)	N2—C7—C8—C9	−24.0 (3)
Cl1—Zn1—O1—C20	112.73 (17)	N1—C7—C8—C13	−28.3 (3)
O1—Zn1—N1—C7	116.26 (16)	N2—C7—C8—C13	155.4 (2)
N3—Zn1—N1—C7	20.19 (17)	C13—C8—C9—C10	0.7 (3)
Cl1—Zn1—N1—C7	−103.02 (16)	C7—C8—C9—C10	−179.9 (2)
O1—Zn1—N1—C1	−55.4 (2)	C8—C9—C10—C11	0.7 (4)
N3—Zn1—N1—C1	−151.41 (18)	C9—C10—C11—C12	−1.2 (4)
Cl1—Zn1—N1—C1	85.37 (18)	C10—C11—C12—C13	0.3 (4)
O1—Zn1—N3—C14	13.98 (18)	C11—C12—C13—C8	1.1 (4)
N1—Zn1—N3—C14	135.10 (18)	C11—C12—C13—N3	−179.0 (2)
Cl1—Zn1—N3—C14	−109.09 (17)	C9—C8—C13—C12	−1.6 (3)
O1—Zn1—N3—C13	−166.00 (15)	C7—C8—C13—C12	179.0 (2)
N1—Zn1—N3—C13	−44.88 (16)	C9—C8—C13—N3	178.56 (19)
Cl1—Zn1—N3—C13	70.93 (16)	C7—C8—C13—N3	−0.8 (3)
C7—N1—C1—C2	179.7 (2)	C14—N3—C13—C12	40.8 (3)
Zn1—N1—C1—C2	−7.7 (3)	Zn1—N3—C13—C12	−139.24 (19)
C7—N1—C1—C6	−0.9 (2)	C14—N3—C13—C8	−139.4 (2)
Zn1—N1—C1—C6	171.74 (15)	Zn1—N3—C13—C8	40.6 (2)
C6—C1—C2—C3	0.7 (3)	C13—N3—C14—C15	174.0 (2)
N1—C1—C2—C3	−180.0 (2)	Zn1—N3—C14—C15	−6.0 (3)
C1—C2—C3—C4	−1.6 (3)	N3—C14—C15—C16	177.5 (2)
C2—C3—C4—C5	1.0 (4)	N3—C14—C15—C20	−7.2 (4)
C3—C4—C5—C6	0.7 (4)	C20—C15—C16—C17	−0.6 (4)
C4—C5—C6—N2	179.1 (2)	C14—C15—C16—C17	175.0 (2)
C4—C5—C6—C1	−1.6 (3)	C15—C16—C17—C18	−1.4 (4)
C7—N2—C6—C5	178.7 (2)	C16—C17—C18—C19	0.5 (4)
C7—N2—C6—C1	−0.7 (2)	C16—C17—C18—C21	179.3 (2)
C2—C1—C6—C5	1.0 (3)	C17—C18—C19—C20	2.6 (4)
N1—C1—C6—C5	−178.5 (2)	C21—C18—C19—C20	−176.2 (2)
C2—C1—C6—N2	−179.6 (2)	Zn1—O1—C20—C19	−174.38 (15)
N1—C1—C6—N2	1.0 (2)	Zn1—O1—C20—C15	6.2 (3)
C1—N1—C7—N2	0.4 (2)	C18—C19—C20—O1	176.0 (2)
Zn1—N1—C7—N2	−173.03 (14)	C18—C19—C20—C15	−4.5 (3)
C1—N1—C7—C8	−176.3 (2)	C16—C15—C20—O1	−177.2 (2)
Zn1—N1—C7—C8	10.3 (3)	C14—C15—C20—O1	7.6 (4)
C6—N2—C7—N1	0.2 (2)	C16—C15—C20—C19	3.4 (3)
C6—N2—C7—C8	177.05 (19)	C14—C15—C20—C19	−171.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N1···Cl1ⁱ	0.75 (3)	2.53 (3)	3.2352 (19)	157 (2)
C2—H2A···O1ⁱⁱ	0.93	2.59	3.425 (3)	149
C12—H12A···Cg1ⁱⁱⁱ	0.93	2.96	3.762 (3)	145
C21—H21C···Cg2^iv	0.96	2.92	3.741 (3)	144

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) x, −y−1/2, z−1/2; (iv) x, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₂₁H₁₆N₃O)Cl]
M_r	427.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.6338 (1), 19.4952 (2), 10.9687 (1)
β (°)	99.675 (1)
V (Å³)	1819.97 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.51
Crystal size (mm)	0.26 × 0.18 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.694, 0.878
No. of measured, independent and observed [I > 2σ(I)] reflections	22729, 5678, 3773
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.719

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.088, 1.03
No. of reflections	5678
No. of parameters	249
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.39

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N1···Cl1ⁱ	0.75 (3)	2.53 (3)	3.2352 (19)	157 (2)
C2—H2A···O1ⁱⁱ	0.93	2.59	3.425 (3)	149
C12—H12A···Cg1ⁱⁱⁱ	0.93	2.96	3.762 (3)	145
C21—H21C···Cg2^iv	0.96	2.92	3.741 (3)	144

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) x, −y−1/2, z−1/2; (iv) x, −y−1/2, z−3/2.

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Malaysian government and Universiti Sains Malaysia for the Research University Grant No. 1001/PKIMIA/815067. NEE thanks Universiti Sains Malaysia for a postdoctoral fellowship and the International University of Africa (Sudan) for providing study leave. The authors also thank the Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chassaing, C., Berger, M., Heckeroth, A., IIg, T., Jaeger, M., Kern, C., Schmid, K. & Uphoff, M. (2008). J. Med. Chem. 51, 1111–1114. Web of Science CrossRef CAS Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S. & Fun, H.-K. (2007). Acta Cryst. E63, o4141–o4142. Web of Science CSD CrossRef IUCr Journals Google Scholar
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, m1062–m1063. Web of Science CSD CrossRef IUCr Journals Google Scholar
Eltayeb, N. E., Teoh, S. G., Quah, C. K., Fun, H.-K. & Adnan, R. (2009). Acta Cryst. E65, o1613–o1614. Web of Science CSD CrossRef IUCr Journals Google Scholar
Eltayeb, N. E., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2011). Acta Cryst. E67, o1721–o1722. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kucukbay, H., Durmaz, R., Orhan, E. & Gunal, S. (2003). Farmaco, 58, 431–437. CAS Google Scholar
Maldonado-Rogado, M. A., Viñuelas-Zahínos, E., Luna-Giles, F. & Bernalte-García, A. (2007). Polyhedron, 26, 3112–3120. Web of Science CSD CrossRef CAS Google Scholar
Podunavac-Kuzmanovic, S. & Cvetkovic, D. (2010). Rev. Roum. Chim. 55, 363–367. CAS Google Scholar
Podunavac-Kuzmanovic, S. O., Leovac, L. M., Perisic-Janjic, N. U., Rogan, J. & Balaz, J. (1999). J. Serb. Chem. Soc. 64, 381–388. CAS Google Scholar
Podunavac-Kuzmanovic, S. O. & Markov, S. L. (2006). Centr. Eur. J. Occupat. Environ. Med. 12, 61–66. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tong, Y.-P. & Ye, B.-H. (2004). Acta Cryst. E60, m1927–m1929. CSD CrossRef IUCr Journals Google Scholar
Xue, F., Luo, X., Ye, C., Ye, W. & Wang, Y. (2011). Bioorg. Med. Chem. 19, 2641–2649. Web of Science CrossRef CAS PubMed Google Scholar

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