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Acta Cryst. (2007). E63, m2294-m2295    [ doi:10.1107/S1600536807038536 ]

Aqua{6,6-dimethyl-2,2'-[o-phenylenebis(nitrilomethylidyne)]diphenolato-[kappa]4O,N,N',O'}zinc(II) chloroform solvate

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

Abstract top

In the title compound, [Zn(C22H18N2O2)(H2O)]·CHCl3, the ZnII centre is in a five-coordinate square-pyramidal N2O3 environment, with the N2O2 set of atoms from the Schiff base ligand forming the basal plane; the water molecule occupies the apical position. Intermolecular O-H...O hydrogen bonds and weak C-H...O interactions link the molecules into a chain along [100]. The chains form sheets parallel to the ac plane.

Comment top

Zinc is an essential element for the normal function of most biological systems. ZnII chelate complexes are studied as models for hydrolytically active enzymes. It also 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 ZnII complexes with Schiff bases are biologically active and show very good cytotoxicity against the leukemic cell (Tarafder et al., 2002). The coordination number of ZnII in the catalytic sites is often lower than six, even though water molecule or hydroxide ion is bound to the metal as an additional ligand. Since our previous investigations (Eltayeb et al., 2007a,b,c) have shown the possibility of formation of a five coordination environment with tetradentate Schiff base ligand, we have extend our synthesis to the title complex and its crystal structure is reported.

The title complex molecule (Fig. 1) is characterized by an approxmately square pyramidal ZnII coordination, with the tetradentate Schiff base ligand in the basal plane (N1, N2, O1 and O2) and a water molecule in the apical site. The Zn atom is almost in the same plane of this basal plane, as indicated by the displacement of 0.0098 Å out of this basal donor atoms in the direction of the apical water molecule. Bond lengths and angles in this Schiff base ligand are very similar to those reported for the other ZnII complexes with Schiff base ligands (Eltayeb et al., 2007a,b,c). The Zn1—N1 and Zn1—N2 distances of 2.0818 (19) Å and 2.0708 (18) Å, respectively lie in the same range as the other five coordination ZnII complexes of Schiff base ligands (Chaudhuri et al., 2007; Eltayeb et al., 2007,b,c). However, the Zn1—O1 and Zn1—O2 distances of 2.0036 (15) Å and 2.0027 (15) Å, respectively, are longer than those observed in other closely related structures (Eltayeb et al., 2007a,b,c) where the Zn—O distances are in the range of 1.9326 (17)–1.9798 (13) Å. Bond angles around Zn1 are in agreement with the values found for similar ZnII complexes (Eltayeb et al., 2007a,b,c). Evidently, changing the substitutional groups on the Schiff base ligands has no effect on the coordination of the tetradentate Schiff base ligands. Bond lengths and angles observed in the structure are normal (Allen et al., 1987).

In the crystal packing (Fig. 2), the water molecule is involved in intermolecular O—H···O hydrogen bonds [O1W—H2WA···O1 and O1W—H1WA···O2; symmetry code 1 − x, -y, 2 − z] and the chloroform molecule is involved in a weak C—H···O intermolecular interaction [C23—H23···O1W; symmetry code 1 − x, −y, 2 − z] (Table 2). The molcecules are linked into one-dimension chains along the a axis. These chains form molecular sheets parallel to the ac plane. The crystal is stabilized by intermolecular O—H···O hydrogen bonds and weak C—H···O interaction.

Related literature top

For normal values of bond lengths, see Allen et al. (1987). For related structures see, for example, Chaudhuri et al. (2007); Eltayeb et al. (2007a,b,c). For literature on the biological activities of related compounds, see: Assaf & Chung (1984); Berg & Shi (1996); Tarafder et al. (2002).

Experimental top

The title compound (I) was synthesized by adding 3-methyl-2-hydroxybenzaldehyde (0.544 g, 4 mmol) into a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol 95% (20 ml). The mixture was refluxed with stirring for half an hour. Zinc chloride (0.272 g, 2 mmol) in ethanol (10 ml) was added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was stirred at room temperature for two hours. A yellow precipitate was obtained, which was washed by about 5 ml e thanol, dried, and then washed by copious amounts of diethyl ether. The precipitate was dissolved in 20 ml of chloroform and single crystals of the title compound were formed after one day of slow evaporation of chloroform at room temperature.

Refinement top

The water H atoms were located in a difference map and isotropically refined. The remainning H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.

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 and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the b axis. Only water and chloroform H atoms were drawn for clarify. Hydrogen bonds are shown as dash lines.
Aqua{6,6-dimethyl-2,2'-[o-phenylenebis(nitrilomethylidyne)]diphenolato- κ4O,N,N',O'}zinc(II) chloroform solvate top
Crystal data top
[Zn(C22H18N2O2)(H2O)]·CHCl3Z = 2
Mr = 545.16F000 = 556
Triclinic, P1Dx = 1.607 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.0115 (1) ÅCell parameters from 5412 reflections
b = 10.7771 (2) Åθ = 2.4–28.0º
c = 12.9018 (2) ŵ = 1.48 mm−1
α = 94.338 (1)ºT = 100.0 (1) K
β = 103.963 (1)ºBlock, yellow
γ = 109.851 (1)º0.32 × 0.21 × 0.15 mm
V = 1126.55 (3) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5412 independent reflections
Radiation source: fine-focus sealed tube4243 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.043
Detector resolution: 8.33 pixels mm-1θmax = 28.0º
T = 100.0(1) Kθmin = 2.4º
ω scansh = −11→11
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −14→13
Tmin = 0.651, Tmax = 0.810l = −16→17
19823 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)] = 0.037H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.077  w = 1/[σ2(Fo2) + (0.0279P)2 + 0.4583P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5412 reflectionsΔρmax = 0.38 e Å−3
299 parametersΔρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Zn(C22H18N2O2)(H2O)]·CHCl3γ = 109.851 (1)º
Mr = 545.16V = 1126.55 (3) Å3
Triclinic, P1Z = 2
a = 9.0115 (1) ÅMo Kα
b = 10.7771 (2) ŵ = 1.48 mm−1
c = 12.9018 (2) ÅT = 100.0 (1) K
α = 94.338 (1)º0.32 × 0.21 × 0.15 mm
β = 103.963 (1)º
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5412 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		4243 reflections with I > 2σ(I)
Tmin = 0.651, Tmax = 0.810Rint = 0.043
19823 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037299 parameters
wR(F2) = 0.077H atoms treated by a mixture of
independent and constrained refinement
S = 1.03Δρmax = 0.38 e Å−3
5412 reflectionsΔρmin = −0.41 e Å−3
Special details top

Experimental. The low-temparture data was 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
Zn10.27559 (3)−0.00780 (3)0.88420 (2)0.01584 (8)
O10.46560 (18)0.16671 (15)0.91153 (12)0.0174 (3)
O20.26547 (18)−0.00680 (15)1.03761 (12)0.0177 (3)
O1W0.4145 (2)−0.12826 (17)0.89043 (14)0.0170 (4)
N10.2252 (2)−0.00472 (18)0.71842 (15)0.0168 (4)
N20.0356 (2)−0.14449 (18)0.83007 (15)0.0159 (4)
C10.5332 (3)0.2309 (2)0.84187 (18)0.0161 (5)
C20.6815 (3)0.3463 (2)0.88245 (19)0.0176 (5)
C30.7567 (3)0.4130 (2)0.81148 (19)0.0207 (5)
H3A0.85380.48730.83930.025*
C40.6930 (3)0.3738 (2)0.6991 (2)0.0220 (5)
H4A0.74740.42010.65290.026*
C50.5491 (3)0.2659 (2)0.65847 (19)0.0198 (5)
H5A0.50490.23990.58370.024*
C60.4655 (3)0.1926 (2)0.72707 (18)0.0172 (5)
C70.3160 (3)0.0813 (2)0.67323 (19)0.0172 (5)
H7A0.28090.07000.59800.021*
C80.0777 (3)−0.1091 (2)0.65642 (18)0.0166 (5)
C90.0306 (3)−0.1450 (2)0.54369 (19)0.0213 (5)
H9A0.0992−0.09920.50430.026*
C10−0.1162 (3)−0.2473 (2)0.4902 (2)0.0224 (5)
H10A−0.1463−0.27020.41510.027*
C11−0.2193 (3)−0.3164 (2)0.54805 (19)0.0207 (5)
H11A−0.3190−0.38480.51170.025*
C12−0.1739 (3)−0.2836 (2)0.65921 (19)0.0194 (5)
H12A−0.2434−0.33080.69750.023*
C13−0.0256 (3)−0.1810 (2)0.71564 (18)0.0153 (5)
C14−0.0571 (3)−0.1917 (2)0.89165 (19)0.0179 (5)
H14A−0.1656−0.24690.85680.022*
C15−0.0096 (3)−0.1677 (2)1.00789 (18)0.0171 (5)
C16−0.1320 (3)−0.2383 (2)1.0558 (2)0.0217 (5)
H16A−0.2348−0.29441.01120.026*
C17−0.1034 (3)−0.2266 (2)1.1652 (2)0.0224 (5)
H17A−0.1839−0.27621.19510.027*
C180.0503 (3)−0.1379 (2)1.2319 (2)0.0222 (5)
H18A0.0701−0.12881.30680.027*
C190.1727 (3)−0.0639 (2)1.19001 (18)0.0181 (5)
C200.1462 (3)−0.0785 (2)1.07590 (18)0.0161 (5)
C210.7545 (3)0.3909 (2)1.00306 (19)0.0225 (5)
H21A0.84400.47581.01770.034*
H21B0.79450.32581.03360.034*
H21C0.67180.39951.03480.034*
C220.3308 (3)0.0367 (2)1.26331 (19)0.0216 (5)
H22A0.32760.03801.33720.032*
H22B0.34500.12381.24490.032*
H22C0.42100.01271.25480.032*
H2WA0.417 (3)−0.158 (3)0.946 (2)0.027 (8)*
H1WA0.507 (4)−0.083 (3)0.891 (2)0.036 (9)*
C230.3000 (3)0.6266 (2)0.7042 (2)0.0232 (5)
H23A0.33190.70660.75860.028*
Cl10.43406 (7)0.54081 (6)0.74705 (6)0.03189 (16)
Cl20.09640 (7)0.52333 (7)0.69353 (6)0.03265 (16)
Cl30.31570 (9)0.67676 (7)0.57947 (5)0.03654 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01532 (13)0.01675 (14)0.01440 (15)0.00447 (10)0.00455 (10)0.00246 (11)
O10.0177 (8)0.0168 (8)0.0156 (8)0.0039 (6)0.0044 (7)0.0038 (7)
O20.0170 (8)0.0203 (8)0.0161 (8)0.0057 (7)0.0068 (7)0.0034 (7)
O1W0.0169 (9)0.0177 (9)0.0154 (9)0.0046 (7)0.0049 (7)0.0034 (7)
N10.0147 (9)0.0157 (10)0.0186 (10)0.0043 (8)0.0043 (8)0.0029 (8)
N20.0165 (9)0.0163 (10)0.0154 (10)0.0071 (8)0.0039 (8)0.0022 (8)
C10.0155 (11)0.0156 (11)0.0203 (12)0.0088 (9)0.0051 (9)0.0059 (10)
C20.0157 (11)0.0166 (12)0.0213 (13)0.0074 (9)0.0044 (10)0.0030 (10)
C30.0167 (11)0.0167 (12)0.0262 (14)0.0040 (9)0.0051 (10)0.0033 (10)
C40.0214 (12)0.0215 (13)0.0241 (14)0.0056 (10)0.0100 (11)0.0094 (11)
C50.0236 (12)0.0228 (13)0.0154 (12)0.0099 (10)0.0070 (10)0.0065 (10)
C60.0165 (11)0.0172 (12)0.0190 (12)0.0076 (9)0.0048 (10)0.0050 (10)
C70.0186 (11)0.0192 (12)0.0149 (12)0.0088 (10)0.0039 (9)0.0035 (10)
C80.0160 (11)0.0169 (12)0.0168 (12)0.0075 (9)0.0025 (9)0.0020 (10)
C90.0244 (12)0.0208 (13)0.0190 (13)0.0072 (10)0.0080 (10)0.0051 (10)
C100.0276 (13)0.0216 (13)0.0161 (13)0.0107 (11)0.0014 (10)−0.0004 (10)
C110.0156 (11)0.0177 (12)0.0225 (13)0.0043 (9)−0.0014 (10)−0.0023 (10)
C120.0191 (11)0.0178 (12)0.0213 (13)0.0072 (10)0.0057 (10)0.0025 (10)
C130.0165 (11)0.0153 (11)0.0155 (12)0.0090 (9)0.0027 (9)0.0030 (9)
C140.0154 (11)0.0156 (12)0.0225 (13)0.0056 (9)0.0048 (10)0.0034 (10)
C150.0185 (11)0.0182 (12)0.0180 (12)0.0091 (9)0.0067 (10)0.0060 (10)
C160.0203 (12)0.0201 (12)0.0277 (14)0.0081 (10)0.0098 (11)0.0076 (11)
C170.0264 (13)0.0220 (13)0.0246 (14)0.0092 (11)0.0153 (11)0.0104 (11)
C180.0313 (13)0.0251 (13)0.0162 (13)0.0143 (11)0.0109 (11)0.0060 (10)
C190.0223 (12)0.0182 (12)0.0180 (12)0.0117 (10)0.0068 (10)0.0047 (10)
C200.0173 (11)0.0147 (11)0.0212 (13)0.0101 (9)0.0076 (10)0.0047 (10)
C210.0217 (12)0.0178 (12)0.0220 (13)0.0021 (10)0.0040 (10)0.0005 (10)
C220.0252 (13)0.0257 (13)0.0166 (13)0.0115 (11)0.0077 (10)0.0036 (10)
C230.0235 (12)0.0231 (13)0.0229 (14)0.0086 (10)0.0078 (11)0.0006 (11)
Cl10.0218 (3)0.0304 (4)0.0445 (4)0.0107 (3)0.0100 (3)0.0058 (3)
Cl20.0204 (3)0.0332 (4)0.0433 (4)0.0078 (3)0.0118 (3)0.0018 (3)
Cl30.0461 (4)0.0358 (4)0.0268 (4)0.0111 (3)0.0145 (3)0.0053 (3)
Geometric parameters (Å, °) top
Zn1—O22.0027 (15)C10—C111.387 (3)
Zn1—O12.0036 (15)C10—H10A0.9300
Zn1—N22.0708 (18)C11—C121.375 (3)
Zn1—O1W2.0810 (16)C11—H11A0.9300
Zn1—N12.0818 (19)C12—C131.394 (3)
O1—C11.315 (3)C12—H12A0.9300
O2—C201.322 (2)C14—C151.434 (3)
O1W—H2WA0.80 (3)C14—H14A0.9300
O1W—H1WA0.81 (3)C15—C161.417 (3)
N1—C71.291 (3)C15—C201.423 (3)
N1—C81.417 (3)C16—C171.360 (3)
N2—C141.296 (3)C16—H16A0.9300
N2—C131.418 (3)C17—C181.405 (3)
C1—C61.427 (3)C17—H17A0.9300
C1—C21.429 (3)C18—C191.379 (3)
C2—C31.372 (3)C18—H18A0.9300
C2—C211.504 (3)C19—C201.421 (3)
C3—C41.397 (3)C19—C221.498 (3)
C3—H3A0.9300C21—H21A0.9600
C4—C51.365 (3)C21—H21B0.9600
C4—H4A0.9300C21—H21C0.9600
C5—C61.413 (3)C22—H22A0.9600
C5—H5A0.9300C22—H22B0.9600
C6—C71.436 (3)C22—H22C0.9600
C7—H7A0.9300C23—Cl21.758 (2)
C8—C91.397 (3)C23—Cl31.759 (2)
C8—C131.412 (3)C23—Cl11.771 (2)
C9—C101.377 (3)C23—H23A0.9800
C9—H9A0.9300
O2—Zn1—O196.84 (6)C11—C10—H10A119.9
O2—Zn1—N289.99 (7)C12—C11—C10119.9 (2)
O1—Zn1—N2158.92 (7)C12—C11—H11A120.1
O2—Zn1—O1W95.73 (7)C10—C11—H11A120.1
O1—Zn1—O1W95.93 (7)C11—C12—C13121.2 (2)
N2—Zn1—O1W103.23 (7)C11—C12—H12A119.4
O2—Zn1—N1164.74 (7)C13—C12—H12A119.4
O1—Zn1—N189.63 (7)C12—C13—C8118.8 (2)
N2—Zn1—N179.38 (7)C12—C13—N2125.3 (2)
O1W—Zn1—N197.34 (7)C8—C13—N2115.88 (19)
C1—O1—Zn1129.18 (14)N2—C14—C15126.8 (2)
C20—O2—Zn1129.59 (14)N2—C14—H14A116.6
Zn1—O1W—H2WA107.6 (19)C15—C14—H14A116.6
Zn1—O1W—H1WA109 (2)C16—C15—C20119.2 (2)
H2WA—O1W—H1WA109 (3)C16—C15—C14115.5 (2)
C7—N1—C8121.5 (2)C20—C15—C14125.2 (2)
C7—N1—Zn1125.23 (16)C17—C16—C15121.9 (2)
C8—N1—Zn1113.26 (14)C17—C16—H16A119.1
C14—N2—C13120.93 (19)C15—C16—H16A119.1
C14—N2—Zn1125.15 (16)C16—C17—C18118.6 (2)
C13—N2—Zn1113.89 (13)C16—C17—H17A120.7
O1—C1—C6123.6 (2)C18—C17—H17A120.7
O1—C1—C2118.7 (2)C19—C18—C17122.1 (2)
C6—C1—C2117.7 (2)C19—C18—H18A118.9
C3—C2—C1119.8 (2)C17—C18—H18A118.9
C3—C2—C21121.1 (2)C18—C19—C20119.8 (2)
C1—C2—C21119.1 (2)C18—C19—C22120.7 (2)
C2—C3—C4122.6 (2)C20—C19—C22119.5 (2)
C2—C3—H3A118.7O2—C20—C19118.7 (2)
C4—C3—H3A118.7O2—C20—C15123.0 (2)
C5—C4—C3118.6 (2)C19—C20—C15118.3 (2)
C5—C4—H4A120.7C2—C21—H21A109.5
C3—C4—H4A120.7C2—C21—H21B109.5
C4—C5—C6121.7 (2)H21A—C21—H21B109.5
C4—C5—H5A119.1C2—C21—H21C109.5
C6—C5—H5A119.1H21A—C21—H21C109.5
C5—C6—C1119.5 (2)H21B—C21—H21C109.5
C5—C6—C7115.7 (2)C19—C22—H22A109.5
C1—C6—C7124.8 (2)C19—C22—H22B109.5
N1—C7—C6126.7 (2)H22A—C22—H22B109.5
N1—C7—H7A116.6C19—C22—H22C109.5
C6—C7—H7A116.6H22A—C22—H22C109.5
C9—C8—C13119.2 (2)H22B—C22—H22C109.5
C9—C8—N1124.8 (2)Cl2—C23—Cl3110.58 (13)
C13—C8—N1115.96 (19)Cl2—C23—Cl1109.94 (13)
C10—C9—C8120.7 (2)Cl3—C23—Cl1110.28 (12)
C10—C9—H9A119.7Cl2—C23—H23A108.7
C8—C9—H9A119.7Cl3—C23—H23A108.7
C9—C10—C11120.2 (2)Cl1—C23—H23A108.7
C9—C10—H10A119.9
O2—Zn1—O1—C1−176.55 (17)C5—C6—C7—N1175.1 (2)
N2—Zn1—O1—C1−68.4 (3)C1—C6—C7—N1−4.0 (4)
O1W—Zn1—O1—C186.93 (17)C7—N1—C8—C912.0 (3)
N1—Zn1—O1—C1−10.41 (17)Zn1—N1—C8—C9−167.72 (18)
O1—Zn1—O2—C20163.81 (17)C7—N1—C8—C13−168.7 (2)
N2—Zn1—O2—C203.80 (18)Zn1—N1—C8—C1311.6 (2)
O1W—Zn1—O2—C20−99.50 (18)C13—C8—C9—C101.3 (3)
N1—Zn1—O2—C2049.3 (3)N1—C8—C9—C10−179.4 (2)
O2—Zn1—N1—C7122.3 (3)C8—C9—C10—C11−0.1 (4)
O1—Zn1—N1—C76.87 (18)C9—C10—C11—C12−0.8 (4)
N2—Zn1—N1—C7168.79 (19)C10—C11—C12—C130.4 (3)
O1W—Zn1—N1—C7−89.06 (18)C11—C12—C13—C80.8 (3)
O2—Zn1—N1—C8−58.0 (3)C11—C12—C13—N2−176.6 (2)
O1—Zn1—N1—C8−173.39 (15)C9—C8—C13—C12−1.7 (3)
N2—Zn1—N1—C8−11.48 (14)N1—C8—C13—C12179.02 (19)
O1W—Zn1—N1—C890.68 (15)C9—C8—C13—N2176.00 (19)
O2—Zn1—N2—C141.06 (18)N1—C8—C13—N2−3.3 (3)
O1—Zn1—N2—C14−108.3 (2)C14—N2—C13—C12−11.3 (3)
O1W—Zn1—N2—C1496.94 (18)Zn1—N2—C13—C12170.87 (17)
N1—Zn1—N2—C14−167.93 (19)C14—N2—C13—C8171.2 (2)
O2—Zn1—N2—C13178.78 (14)Zn1—N2—C13—C8−6.6 (2)
O1—Zn1—N2—C1369.5 (2)C13—N2—C14—C15177.3 (2)
O1W—Zn1—N2—C13−85.34 (15)Zn1—N2—C14—C15−5.1 (3)
N1—Zn1—N2—C139.79 (14)N2—C14—C15—C16−176.2 (2)
Zn1—O1—C1—C68.5 (3)N2—C14—C15—C205.1 (4)
Zn1—O1—C1—C2−172.26 (14)C20—C15—C16—C17−2.0 (3)
O1—C1—C2—C3178.4 (2)C14—C15—C16—C17179.1 (2)
C6—C1—C2—C3−2.3 (3)C15—C16—C17—C182.3 (4)
O1—C1—C2—C21−0.4 (3)C16—C17—C18—C19−0.6 (4)
C6—C1—C2—C21178.9 (2)C17—C18—C19—C20−1.3 (3)
C1—C2—C3—C40.8 (3)C17—C18—C19—C22175.7 (2)
C21—C2—C3—C4179.5 (2)Zn1—O2—C20—C19176.74 (14)
C2—C3—C4—C51.0 (4)Zn1—O2—C20—C15−4.8 (3)
C3—C4—C5—C6−1.0 (3)C18—C19—C20—O2−179.9 (2)
C4—C5—C6—C1−0.6 (3)C22—C19—C20—O23.1 (3)
C4—C5—C6—C7−179.8 (2)C18—C19—C20—C151.6 (3)
O1—C1—C6—C5−178.50 (19)C22—C19—C20—C15−175.5 (2)
C2—C1—C6—C52.3 (3)C16—C15—C20—O2−178.5 (2)
O1—C1—C6—C70.6 (3)C14—C15—C20—O20.3 (3)
C2—C1—C6—C7−178.7 (2)C16—C15—C20—C190.0 (3)
C8—N1—C7—C6178.6 (2)C14—C15—C20—C19178.7 (2)
Zn1—N1—C7—C6−1.7 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H2WA···O1i0.81 (3)1.91 (3)2.646 (2)151 (3)
O1W—H1WA···O2i0.81 (4)1.90 (3)2.636 (3)152 (3)
C23—H23A···O1Wii0.982.163.132 (3)174
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H2WA···O1i0.81 (3)1.91 (3)2.646 (2)151 (3)
O1W—H1WA···O2i0.81 (4)1.90 (3)2.636 (3)152 (3)
C23—H23A···O1Wii0.982.163.132 (3)174
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x, y+1, z.
Acknowledgements top

The authors thank the Malaysian Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia for an E-Science Fund research grant (PKIMIA/613308) and facilities. The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. The authors also thank Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) (grant No. 203/PFIZIK/671064.

references
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