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Acta Cryst. (2007). E63, m1284-m1285    [ doi:10.1107/S1600536807017618 ]

{2,2'-[1,2-Phenylenebis(nitrilomethylidyne)]diphenolato-[kappa]4O,N,N',O'}(pyridine-[kappa]N)zinc(II)

N. E. Eltayeb, S. G. Teoh, S.-L. Ng, H.-K. Fun and K. Ibrahim

Abstract top

In the title compound, [Zn(C20H14N2O2)(C5H5N)], the ZnII atom is in a distorted square-pyramidal environment. In the crystal structure, intermolecular C-H...O interactions interconnect the molecules into wave-like chains along the c axis. In addition, the crystal packing is further stabilized by weak C-H...[pi] interactions.

Comment top

Zinc, an element of strong interest in biology, medicine, materials and catalysis, plays important roles in various biological systems, such as neurotransmission, signal transduction and gene expression (Assaf & Chung, 1984; Berg & Shi, 1996). It is well known that zinc complexes with Schiff bases show very good activity against the leukaemic cell (Tarafder et al., 2002). Here, we report the crystal structure of the title ZnII complex, (I), with the 2,2'-{1,2-phenylenebis[nitrilomethylylide]}diphenol Schiff base.

The ZnII atom in (I) is five-coordinated by two O atoms and two N atoms in the basal plane, together with the N atom of the pyridine ring in the apical position, giving a distorted square-pyramidal geometry (Fig. 1 and Table 1). The ZnII ion is displaced from the basal plane (N1/N2/O2/O1) by 0.3975 (2) Å. The N3/C21–C25 pyridine ring is attached axially to Zn1 with the torsion angle O1—Zn1—N3—C25 = -3.93 (15)°. The bond lengths and angles in (I) have normal values (Allen et al., 1987).

An intramolecular C25—H25A···O1 interaction (Table 2 and Fig. 1) generates S(5) ring motifs (Bernstein et al., 1995). In the crystal structure, the molecules are linked by intermolecular C23—H23A···O2 interactions into wave-like chains along the c axis (Fig. 2). In addition, the crystal packing is further stabilized by weak intermolecular C—H···π interactions involving the Zn1/O1/C1/C6/C7/N1 ring (centroid Cg1) (Table 2).

Related literature top

For related literature, see: Allen et al. (1987); Assaf & Chung (1984); Berg & Shi (1996); Bernstein et al. (1995); Tarafder et al. (2002).

Experimental top

The title compound was synthesized as follows. To a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol (20 ml) was added 2-hydroxybenzaldehyde (0.4 ml, 4 mmol). The mixture was refluxed with stirring for half an hour. Zinc chloride (0.272 g, 2 mmol) in ethanol (10 ml) was then added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was stirred at

room temperature for 2 h, following which the yellow precipitate obtained was washed with ethanol (about 5 ml), dried and then washed in a copious amount of diethyl ether. This precipitate was dissolved in pyridine (15 ml), and after 9 d of slow evaporation of the pyridine at room temperature, yellow crystals of

(I) suitable for X-ray diffraction analysis were formed.

Refinement top

H atoms were positioned geometrically and treated as riding, with C—H = 0.93 Å and the Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. The dashed line indicates the intramolecular hydrogen bond.
[Figure 2] Fig. 2. The crystal packing of (I), viewed down the a axis. The intermolecular C—H···O hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
[2,2'-{1,2-Phenylenebis(nitrilomethylylidyne)}diphenolato- κ4O,N,N',O'](pyridine-κN)zinc(II) top
Crystal data top
[Zn(C20H14N2O2)(C5H5N)]F(000) = 944
Mr = 458.80Dx = 1.505 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 9040 reflections
a = 17.8611 (3) Åθ = 2.1–40.0°
b = 11.9929 (3) ŵ = 1.24 mm−1
c = 9.4946 (2) ÅT = 100 K
β = 95.540 (1)°Block, yellow
V = 2024.30 (7) Å30.53 × 0.38 × 0.21 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		11416 independent reflections
Radiation source: fine-focus sealed tube9121 reflections with I > 2σ(I)
graphiteRint = 0.047
Detector resolution: 8.33 pixels mm-1θmax = 40.0°, θmin = 2.1°
ω scansh = −31→31
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −19→21
Tmin = 0.588, Tmax = 0.778l = −17→16
31548 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + 1.0902P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
11416 reflectionsΔρmax = 0.87 e Å−3
280 parametersΔρmin = −0.92 e Å−3
2 restraintsAbsolute structure: Flack (1983), with 5258 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.014 (7)
Crystal data top
[Zn(C20H14N2O2)(C5H5N)]V = 2024.30 (7) Å3
Mr = 458.80Z = 4
Monoclinic, CcMo Kα radiation
a = 17.8611 (3) ŵ = 1.24 mm−1
b = 11.9929 (3) ÅT = 100 K
c = 9.4946 (2) Å0.53 × 0.38 × 0.21 mm
β = 95.540 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		11416 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		9121 reflections with I > 2σ(I)
Tmin = 0.588, Tmax = 0.778Rint = 0.047
31548 measured reflectionsθmax = 40.0°
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.104Δρmax = 0.87 e Å−3
S = 1.07Δρmin = −0.92 e Å−3
11416 reflectionsAbsolute structure: Flack (1983), with 5258 Friedel pairs
280 parametersFlack parameter: 0.014 (7)
2 restraints
Special details top

Experimental. The data were collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
xyzUiso*/Ueq
Zn10.137941 (15)0.276624 (17)0.931457 (18)0.01513 (4)
O10.05548 (8)0.26576 (14)1.05451 (15)0.0210 (3)
O20.22018 (8)0.28305 (14)1.08423 (15)0.0213 (3)
N10.06264 (9)0.35148 (15)0.77673 (16)0.0166 (3)
N20.21070 (8)0.35007 (15)0.79573 (15)0.0161 (3)
C1−0.01125 (10)0.30971 (18)1.04053 (19)0.0178 (3)
C2−0.05900 (11)0.29339 (19)1.1504 (2)0.0212 (4)
H2A−0.04180.25021.22820.025*
C3−0.12951 (11)0.3392 (2)1.1455 (2)0.0245 (4)
H3A−0.15870.32731.22000.029*
C4−0.15823 (12)0.4040 (2)1.0294 (2)0.0258 (4)
H4A−0.20600.43531.02650.031*
C5−0.11409 (12)0.4202 (2)0.9195 (2)0.0224 (4)
H5A−0.13280.46300.84230.027*
C6−0.04126 (12)0.3736 (2)0.9211 (2)0.0176 (4)
C7−0.00347 (10)0.39031 (18)0.79527 (19)0.0180 (3)
H7A−0.02820.43180.72230.022*
C80.09499 (10)0.36759 (17)0.64817 (18)0.0167 (3)
C90.05405 (11)0.37665 (18)0.51553 (19)0.0189 (3)
H9A0.00180.37510.50790.023*
C100.09183 (12)0.38795 (18)0.3952 (2)0.0197 (3)
H10A0.06460.39500.30710.024*
C110.17024 (12)0.38874 (18)0.4054 (2)0.0200 (3)
H11A0.19500.39630.32400.024*
C120.21155 (11)0.37828 (18)0.53604 (19)0.0190 (3)
H12A0.26380.37840.54230.023*
C130.17443 (10)0.36752 (16)0.65840 (17)0.0157 (3)
C140.27789 (10)0.38710 (17)0.83114 (18)0.0174 (3)
H14A0.30150.42570.76290.021*
C150.31893 (12)0.3730 (2)0.9683 (2)0.0175 (4)
C160.39295 (12)0.4161 (2)0.9850 (2)0.0232 (4)
H16A0.41210.45040.90840.028*
C170.43724 (12)0.4087 (2)1.1108 (2)0.0246 (4)
H17A0.48590.43731.11930.030*
C180.40826 (11)0.35744 (19)1.2266 (2)0.0207 (3)
H18A0.43800.35161.31230.025*
C190.33618 (11)0.31565 (19)1.21453 (19)0.0201 (3)
H19A0.31830.28221.29300.024*
C200.28810 (10)0.32175 (17)1.08643 (18)0.0172 (3)
N30.13875 (8)0.11047 (15)0.86487 (16)0.0172 (3)
C210.18650 (11)0.07344 (18)0.7742 (2)0.0197 (3)
H21A0.21770.12470.73510.024*
C220.19123 (11)−0.03757 (19)0.7364 (2)0.0218 (3)
H22A0.2259−0.06030.67520.026*
C230.14410 (12)−0.11397 (18)0.7905 (2)0.0213 (3)
H23A0.1456−0.18880.76530.026*
C240.09411 (12)−0.0766 (2)0.8840 (2)0.0230 (4)
H24A0.0619−0.12630.92310.028*
C250.09292 (11)0.03505 (19)0.9177 (2)0.0201 (3)
H25A0.05910.05950.97960.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01612 (7)0.01586 (9)0.01368 (7)0.00019 (10)0.00283 (5)0.00089 (9)
O10.0196 (6)0.0259 (8)0.0182 (6)0.0050 (5)0.0054 (5)0.0034 (5)
O20.0199 (6)0.0276 (8)0.0164 (5)−0.0057 (5)0.0021 (4)0.0040 (5)
N10.0186 (6)0.0166 (8)0.0149 (6)−0.0004 (5)0.0034 (5)0.0002 (5)
N20.0184 (6)0.0164 (7)0.0134 (6)−0.0002 (5)0.0017 (4)0.0011 (5)
C10.0175 (7)0.0189 (9)0.0174 (7)−0.0007 (6)0.0035 (5)−0.0024 (6)
C20.0207 (8)0.0237 (10)0.0197 (7)−0.0006 (7)0.0040 (6)−0.0008 (7)
C30.0212 (8)0.0305 (12)0.0228 (8)−0.0017 (7)0.0073 (6)−0.0043 (8)
C40.0187 (8)0.0315 (12)0.0278 (9)0.0040 (7)0.0049 (7)−0.0042 (8)
C50.0192 (8)0.0251 (11)0.0229 (9)0.0024 (7)0.0016 (7)−0.0014 (8)
C60.0171 (8)0.0171 (9)0.0189 (8)−0.0002 (6)0.0025 (6)−0.0029 (7)
C70.0192 (7)0.0178 (9)0.0169 (7)0.0003 (6)0.0012 (6)0.0003 (6)
C80.0204 (7)0.0148 (8)0.0147 (7)0.0003 (6)0.0013 (5)0.0002 (6)
C90.0218 (8)0.0180 (9)0.0164 (7)0.0023 (6)−0.0004 (6)0.0000 (6)
C100.0289 (9)0.0161 (9)0.0140 (7)0.0012 (7)0.0012 (6)0.0013 (6)
C110.0299 (9)0.0172 (9)0.0131 (7)0.0001 (7)0.0030 (6)0.0010 (6)
C120.0233 (8)0.0182 (9)0.0164 (7)−0.0006 (6)0.0057 (6)0.0026 (6)
C130.0190 (7)0.0145 (8)0.0138 (6)−0.0011 (6)0.0026 (5)0.0008 (5)
C140.0196 (7)0.0179 (9)0.0153 (7)−0.0011 (6)0.0043 (5)0.0019 (6)
C150.0192 (8)0.0180 (10)0.0154 (7)−0.0004 (7)0.0016 (6)0.0025 (6)
C160.0202 (8)0.0297 (12)0.0196 (8)−0.0042 (7)0.0010 (7)0.0049 (8)
C170.0198 (8)0.0306 (12)0.0228 (8)−0.0050 (7)−0.0005 (6)0.0050 (8)
C180.0215 (8)0.0213 (10)0.0186 (7)0.0003 (7)−0.0018 (6)0.0016 (7)
C190.0218 (8)0.0216 (10)0.0166 (7)−0.0018 (7)0.0012 (6)0.0025 (7)
C200.0203 (7)0.0162 (9)0.0150 (7)−0.0005 (6)0.0020 (5)0.0004 (6)
N30.0151 (6)0.0192 (8)0.0174 (6)−0.0001 (5)0.0023 (5)0.0010 (5)
C210.0201 (7)0.0184 (9)0.0213 (8)−0.0015 (6)0.0059 (6)−0.0017 (7)
C220.0239 (8)0.0214 (10)0.0208 (8)0.0011 (7)0.0059 (6)−0.0013 (7)
C230.0292 (9)0.0160 (9)0.0187 (7)−0.0009 (7)0.0020 (6)−0.0022 (6)
C240.0262 (9)0.0214 (10)0.0222 (8)−0.0056 (7)0.0062 (7)−0.0007 (7)
C250.0204 (8)0.0217 (10)0.0188 (7)−0.0025 (6)0.0052 (6)0.0003 (7)
Geometric parameters (Å, °) top
Zn1—O21.9637 (14)C10—H10A0.9300
Zn1—O11.9707 (14)C11—C121.387 (3)
Zn1—N32.0910 (18)C11—H11A0.9300
Zn1—N12.0956 (16)C12—C131.398 (2)
Zn1—N22.1092 (15)C12—H12A0.9300
O1—C11.298 (2)C14—C151.441 (3)
O2—C201.297 (2)C14—H14A0.9300
N1—C71.297 (2)C15—C161.414 (3)
N1—C81.413 (2)C15—C201.435 (3)
N2—C141.293 (2)C16—C171.371 (3)
N2—C131.414 (2)C16—H16A0.9300
C1—C21.423 (3)C17—C181.402 (3)
C1—C61.429 (3)C17—H17A0.9300
C2—C31.371 (3)C18—C191.376 (3)
C2—H2A0.9300C18—H18A0.9300
C3—C41.405 (3)C19—C201.421 (3)
C3—H3A0.9300C19—H19A0.9300
C4—C51.380 (3)N3—C211.345 (2)
C4—H4A0.9300N3—C251.349 (3)
C5—C61.414 (3)C21—C221.383 (3)
C5—H5A0.9300C21—H21A0.9300
C6—C71.442 (3)C22—C231.377 (3)
C7—H7A0.9300C22—H22A0.9300
C8—C91.398 (3)C23—C241.392 (3)
C8—C131.413 (2)C23—H23A0.9300
C9—C101.388 (3)C24—C251.377 (3)
C9—H9A0.9300C24—H24A0.9300
C10—C111.395 (3)C25—H25A0.9300
O2—Zn1—O196.51 (6)C12—C11—C10120.33 (18)
O2—Zn1—N3103.55 (7)C12—C11—H11A119.8
O1—Zn1—N398.26 (6)C10—C11—H11A119.8
O2—Zn1—N1152.21 (7)C11—C12—C13119.86 (18)
O1—Zn1—N188.75 (6)C11—C12—H12A120.1
N3—Zn1—N1102.65 (6)C13—C12—H12A120.1
O2—Zn1—N288.50 (6)C12—C13—C8119.77 (16)
O1—Zn1—N2158.38 (7)C12—C13—N2124.61 (16)
N3—Zn1—N2100.99 (6)C8—C13—N2115.54 (14)
N1—Zn1—N277.55 (6)N2—C14—C15124.96 (17)
C1—O1—Zn1130.08 (13)N2—C14—H14A117.5
C20—O2—Zn1131.12 (12)C15—C14—H14A117.5
C7—N1—C8121.44 (16)C16—C15—C20119.59 (18)
C7—N1—Zn1126.14 (12)C16—C15—C14116.58 (18)
C8—N1—Zn1112.07 (12)C20—C15—C14123.80 (19)
C14—N2—C13121.32 (15)C17—C16—C15121.96 (19)
C14—N2—Zn1126.56 (12)C17—C16—H16A119.0
C13—N2—Zn1111.75 (11)C15—C16—H16A119.0
O1—C1—C2118.57 (18)C16—C17—C18119.09 (19)
O1—C1—C6124.69 (17)C16—C17—H17A120.5
C2—C1—C6116.73 (18)C18—C17—H17A120.5
C3—C2—C1122.2 (2)C19—C18—C17120.51 (18)
C3—C2—H2A118.9C19—C18—H18A119.7
C1—C2—H2A118.9C17—C18—H18A119.7
C2—C3—C4120.89 (18)C18—C19—C20122.40 (17)
C2—C3—H3A119.6C18—C19—H19A118.8
C4—C3—H3A119.6C20—C19—H19A118.8
C5—C4—C3118.62 (19)O2—C20—C19118.83 (16)
C5—C4—H4A120.7O2—C20—C15124.72 (17)
C3—C4—H4A120.7C19—C20—C15116.44 (17)
C4—C5—C6121.9 (2)C21—N3—C25117.51 (18)
C4—C5—H5A119.1C21—N3—Zn1122.12 (14)
C6—C5—H5A119.1C25—N3—Zn1120.30 (13)
C5—C6—C1119.63 (18)N3—C21—C22122.83 (19)
C5—C6—C7116.1 (2)N3—C21—H21A118.6
C1—C6—C7124.18 (18)C22—C21—H21A118.6
N1—C7—C6124.60 (18)C23—C22—C21119.27 (18)
N1—C7—H7A117.7C23—C22—H22A120.4
C6—C7—H7A117.7C21—C22—H22A120.4
C9—C8—C13119.77 (16)C22—C23—C24118.4 (2)
C9—C8—N1124.52 (16)C22—C23—H23A120.8
C13—C8—N1115.61 (15)C24—C23—H23A120.8
C10—C9—C8119.68 (18)C25—C24—C23119.12 (19)
C10—C9—H9A120.2C25—C24—H24A120.4
C8—C9—H9A120.2C23—C24—H24A120.4
C9—C10—C11120.59 (19)N3—C25—C24122.81 (17)
C9—C10—H10A119.7N3—C25—H25A118.6
C11—C10—H10A119.7C24—C25—H25A118.6
O2—Zn1—O1—C1142.18 (19)C8—C9—C10—C110.9 (3)
N3—Zn1—O1—C1−113.06 (19)C9—C10—C11—C120.0 (3)
N1—Zn1—O1—C1−10.46 (19)C10—C11—C12—C13−0.4 (3)
N2—Zn1—O1—C139.7 (3)C11—C12—C13—C8−0.1 (3)
O1—Zn1—O2—C20−157.39 (19)C11—C12—C13—N2176.26 (19)
N3—Zn1—O2—C20102.47 (19)C9—C8—C13—C121.0 (3)
N1—Zn1—O2—C20−57.7 (3)N1—C8—C13—C12177.39 (18)
N2—Zn1—O2—C201.53 (19)C9—C8—C13—N2−175.69 (18)
O2—Zn1—N1—C7−88.4 (2)N1—C8—C13—N20.7 (3)
O1—Zn1—N1—C713.18 (18)C14—N2—C13—C1229.3 (3)
N3—Zn1—N1—C7111.36 (18)Zn1—N2—C13—C12−157.32 (16)
N2—Zn1—N1—C7−149.98 (19)C14—N2—C13—C8−154.23 (19)
O2—Zn1—N1—C884.83 (18)Zn1—N2—C13—C819.2 (2)
O1—Zn1—N1—C8−173.55 (13)C13—N2—C14—C15−180.0 (2)
N3—Zn1—N1—C8−75.36 (14)Zn1—N2—C14—C157.7 (3)
N2—Zn1—N1—C823.29 (13)N2—C14—C15—C16177.8 (2)
O2—Zn1—N2—C14−5.67 (18)N2—C14—C15—C20−4.2 (4)
O1—Zn1—N2—C1498.3 (2)C20—C15—C16—C171.2 (4)
N3—Zn1—N2—C14−109.17 (18)C14—C15—C16—C17179.4 (2)
N1—Zn1—N2—C14150.13 (19)C15—C16—C17—C18−0.3 (4)
O2—Zn1—N2—C13−178.67 (14)C16—C17—C18—C19−0.4 (4)
O1—Zn1—N2—C13−74.7 (2)C17—C18—C19—C200.2 (3)
N3—Zn1—N2—C1377.82 (13)Zn1—O2—C20—C19179.71 (15)
N1—Zn1—N2—C13−22.88 (13)Zn1—O2—C20—C150.8 (3)
Zn1—O1—C1—C2−176.48 (15)C18—C19—C20—O2−178.2 (2)
Zn1—O1—C1—C64.0 (3)C18—C19—C20—C150.7 (3)
O1—C1—C2—C3178.4 (2)C16—C15—C20—O2177.5 (2)
C6—C1—C2—C3−2.0 (3)C14—C15—C20—O2−0.5 (4)
C1—C2—C3—C40.8 (4)C16—C15—C20—C19−1.4 (3)
C2—C3—C4—C50.3 (4)C14—C15—C20—C19−179.4 (2)
C3—C4—C5—C60.0 (4)O2—Zn1—N3—C21−82.04 (15)
C4—C5—C6—C1−1.3 (4)O1—Zn1—N3—C21179.17 (15)
C4—C5—C6—C7175.6 (2)N1—Zn1—N3—C2188.61 (15)
O1—C1—C6—C5−178.2 (2)N2—Zn1—N3—C219.07 (16)
C2—C1—C6—C52.3 (3)O2—Zn1—N3—C2594.86 (15)
O1—C1—C6—C75.1 (4)O1—Zn1—N3—C25−3.93 (15)
C2—C1—C6—C7−174.4 (2)N1—Zn1—N3—C25−94.50 (15)
C8—N1—C7—C6177.53 (19)N2—Zn1—N3—C25−174.04 (14)
Zn1—N1—C7—C6−9.8 (3)C25—N3—C21—C22−1.4 (3)
C5—C6—C7—N1−178.3 (2)Zn1—N3—C21—C22175.55 (16)
C1—C6—C7—N1−1.5 (4)N3—C21—C22—C231.6 (3)
C7—N1—C8—C9−30.6 (3)C21—C22—C23—C24−1.2 (3)
Zn1—N1—C8—C9155.77 (17)C22—C23—C24—C250.7 (3)
C7—N1—C8—C13153.21 (19)C21—N3—C25—C240.9 (3)
Zn1—N1—C8—C13−20.4 (2)Zn1—N3—C25—C24−176.16 (16)
C13—C8—C9—C10−1.4 (3)C23—C24—C25—N3−0.5 (3)
N1—C8—C9—C10−177.44 (19)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C25—H25A···O10.932.583.156 (3)121
C23—H23A···O2i0.932.543.211 (3)129
C18—H18A···Cg1ii0.932.873.537 (2)130
Symmetry codes: (i) x, −y, z−1/2; (ii) x+1/2, −y+1/2, z+1/2.
Table 1
Selected geometric parameters (Å, °) top
Zn1—O21.9637 (14)Zn1—N12.0956 (16)
Zn1—O11.9707 (14)Zn1—N22.1092 (15)
Zn1—N32.0910 (18)
O2—Zn1—O196.51 (6)N3—Zn1—N1102.65 (6)
O2—Zn1—N3103.55 (7)O2—Zn1—N288.50 (6)
O1—Zn1—N398.26 (6)O1—Zn1—N2158.38 (7)
O2—Zn1—N1152.21 (7)N3—Zn1—N2100.99 (6)
O1—Zn1—N188.75 (6)N1—Zn1—N277.55 (6)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C25—H25A···O10.932.583.156 (3)121
C23—H23A···O2i0.932.543.211 (3)129
C18—H18A···Cg1ii0.932.873.537 (2)130
Symmetry codes: (i) x, −y, z−1/2; (ii) x+1/2, −y+1/2, z+1/2.
Acknowledgements top

The authors thank the Malaysian Government, Academy of Sciences Malaysia and Universiti Sains Malaysia for a research grant and facilities. The International University of Africa (Sudan) is acknowledged for providing study leave to NEE.

references
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