supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers buy article online

Acta Cryst. (2007). E63, m1764-m1765    [ doi:10.1107/S160053680702380X ]

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

N. E. Eltayeb, S. G. Teoh, J. B.-J. Teh, H.-K. Fun and K. Ibrahim

Abstract top

In the title compound, [Zn(C20H12Br2N2O2)(C5H5N)], the ZnII atom is in a distorted square-pyramidal environment in both independent molecules. The crystal structure is stabilized by C-H...O and C-H...[pi] interactions, together with short Br...N contacts.

Comment top

Recently, we reported the crystal structure of {2,2'-[1,2-phenylenebis(nitrilomethylylidyne)]diphenolato}pyridinezinc (Eltayeb, Teoh, Ng et al., 2007) and aqua{4,4'-dimethoxy-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenolato}zinc (Eltayeb, Teoh, Chantrapromma et al., 2007). The structure of the zinc derivative of 2,2'-{1,2-phenylenebis[nitrilomethylidene]}bis(4-bromophenol) is described here.

There are two independent molecules. The Zn atom is five-coordinate, with the two O atoms and two N atoms forming the basal plane, and with the N atom of the pyridine ring in the apical position, to give a square-pyramidal geometry (Fig. 1 and Table 1). In molecule A, the ZnII ion is displaced from the basal plane (N1A/N2A/O2A/O1A) by -0.3918 (3) Å. The pyridine ring of N3A/C8A—C12A is attached axially to Zn1A with O1A—Zn1A—N3A—C8A torsion angle of 78.5 (2)°. In molecule B, the ZnII ion is displaced from the basal plane (N1B/N2B/O2B/O1B) by -0.3765 (3) Å. The pyridine ring of N3B/C8B—C12B is attached axially to Zn1B with O1B—Zn1B—N3B—C8B torsion angle of 73.6 (2)°. The bond lengths and angles in (I) have normal values (Allen et al., 1987), comparable with those found in the two related structures (Eltayeb, Teoh, Ng et al., 2007; Eltayeb, Teoh, Chantrapromma et al.,2007).

Intramolecular C8B—H8BA···N1B and C12A—H12A···O2A interactions generate S(5) ring motifs (Fig. 1 and Table 2) (Bernstein et al., 1995). The crystal structure (Fig. 2) is stabilized by C—H···O and C—H···π interactions, the latter involving N3A/C8A—C12A (centroid Cg1) and N3B/C8B—C12B (centroid Cg2) rings (Table 2). The relatively short distance [3.392 (2) Å] between the Br2B and N1Bi [symmetry code: (i) 1 - x,1 - y,1 - z] atoms indicate the presence of intermolecular Br···N interactions, which contribute to the further stabilization of the crystal packing.

Related literature top

For related structures, see Eltayeb, Teoh, Ng et al. (2007); Eltayeb, Teoh, Chantrapromma et al. (2007).

For related literature, see: Allen et al. (1987); Bernstein et al. (1995).

Experimental top

To a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol (20 ml) was added 5-bromosalicylaldehyde (0.804 g, 4 mmol). The mixture was refluxed with stirring for half an hour. Zinc chloride (0.272 g, 2 mmol) in 10 ml e thanol was then added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was stirred at room temperature for two h. The yellow precipitate that was obtained was washed by about 5 ml e thanol, dried, and then washed with diethyl ether. This precipitate was dissolved in 15 ml of pyridine, following which orange crystals were formed after two weeks.

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 and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Intramolecular hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. The crystal packing of (I), viewed down the b axis. H atoms not involved in intermolecular hydrogen bonding have been omitted.
{4,4'-Dibromo-2,2'-[1,2-phenylenebis(nitrilomethylidene)]diphenolato-\ κ4O,O',N,N'}(pyridine-κN)zinc(II) top
Crystal data top
[Zn(C20H12Br2N2O2)(C5H5N)]Z = 4
Mr = 616.61F(000) = 1216
Triclinic, P1Dx = 1.834 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0236 (2) ÅCell parameters from 7987 reflections
b = 12.7930 (3) Åθ = 0.9–25.0°
c = 22.4773 (7) ŵ = 4.71 mm−1
α = 91.989 (2)°T = 100 K
β = 94.233 (2)°Block, yellow
γ = 103.566 (2)°0.48 × 0.32 × 0.31 mm
V = 2233.49 (10) Å3
Data collection top
Bruker SMART APEX II CCD
diffractometer		7830 independent reflections
Radiation source: fine-focus sealed tube6908 reflections with I > 2σ(I)
graphiteRint = 0.036
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 0.9°
ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −15→15
Tmin = 0.213, Tmax = 0.319l = −26→26
36723 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0335P)2 + 2.2079P]
where P = (Fo2 + 2Fc2)/3
7830 reflections(Δ/σ)max = 0.002
595 parametersΔρmax = 0.70 e Å−3
0 restraintsΔρmin = −0.62 e Å−3
Crystal data top
[Zn(C20H12Br2N2O2)(C5H5N)]γ = 103.566 (2)°
Mr = 616.61V = 2233.49 (10) Å3
Triclinic, P1Z = 4
a = 8.0236 (2) ÅMo Kα radiation
b = 12.7930 (3) ŵ = 4.71 mm−1
c = 22.4773 (7) ÅT = 100 K
α = 91.989 (2)°0.48 × 0.32 × 0.31 mm
β = 94.233 (2)°
Data collection top
Bruker SMART APEX II CCD
diffractometer		7830 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		6908 reflections with I > 2σ(I)
Tmin = 0.213, Tmax = 0.319Rint = 0.036
36723 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.068Δρmax = 0.70 e Å−3
S = 1.06Δρmin = −0.62 e Å−3
7830 reflectionsAbsolute structure: ?
595 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Experimental. The 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
Br1A−0.07547 (5)−0.23450 (2)0.726142 (16)0.03649 (9)
Br2A0.60641 (4)0.81989 (2)1.039570 (13)0.02463 (8)
Zn1A0.07733 (4)0.30831 (2)0.885341 (14)0.01721 (8)
O1A0.1376 (2)0.22931 (15)0.81676 (9)0.0202 (4)
O2A0.2470 (2)0.44360 (15)0.87258 (9)0.0213 (4)
N1A−0.0375 (3)0.15936 (18)0.91996 (11)0.0193 (5)
N2A0.0960 (3)0.34958 (18)0.97641 (10)0.0176 (5)
C1A−0.0541 (3)0.0659 (2)0.89351 (13)0.0202 (6)
H1AA−0.10030.00600.91450.024*
C2A−0.0075 (4)0.0465 (2)0.83453 (13)0.0204 (6)
C3A−0.0542 (4)−0.0613 (2)0.81136 (14)0.0229 (6)
H3AA−0.1146−0.11460.83400.027*
C4A−0.0119 (4)−0.0883 (2)0.75623 (14)0.0258 (7)
C5A0.0815 (4)−0.0104 (2)0.72177 (14)0.0260 (7)
H5AA0.1104−0.02970.68430.031*
C6A0.1305 (4)0.0944 (2)0.74322 (14)0.0236 (6)
H6AA0.19460.14530.72010.028*
C7A0.0868 (3)0.1283 (2)0.79977 (13)0.0190 (6)
N3A−0.1462 (3)0.34966 (19)0.85053 (10)0.0198 (5)
C8A−0.2992 (4)0.2786 (3)0.84481 (13)0.0249 (6)
H8AA−0.30600.20990.85810.030*
C9A−0.4477 (4)0.3031 (3)0.81993 (15)0.0336 (8)
H9AA−0.55200.25180.81630.040*
C10A−0.4367 (5)0.4056 (3)0.80067 (15)0.0374 (8)
H10A−0.53430.42460.78400.045*
C11A−0.2805 (5)0.4794 (3)0.80621 (15)0.0346 (8)
H11A−0.27090.54880.79340.042*
C12A−0.1382 (4)0.4486 (2)0.83108 (13)0.0254 (6)
H12A−0.03250.49840.83450.030*
C13A0.3222 (3)0.5223 (2)0.91086 (13)0.0192 (6)
C14A0.4374 (4)0.6135 (2)0.89022 (13)0.0219 (6)
H14A0.45750.61430.85000.026*
C15A0.5198 (4)0.7000 (2)0.92751 (14)0.0224 (6)
H15A0.59390.75860.91260.027*
C16A0.4917 (4)0.6997 (2)0.98794 (13)0.0201 (6)
C17A0.3854 (4)0.6139 (2)1.01044 (13)0.0204 (6)
H17A0.37010.61451.05110.024*
C18A0.2982 (4)0.5240 (2)0.97296 (13)0.0187 (6)
C19A0.1925 (3)0.4375 (2)1.00225 (13)0.0189 (6)
H19A0.19350.44541.04360.023*
C20A−0.0057 (3)0.2711 (2)1.00963 (13)0.0197 (6)
C21A−0.0413 (4)0.2875 (2)1.06881 (13)0.0219 (6)
H21A0.00780.35311.08940.026*
C22A−0.1484 (4)0.2073 (2)1.09675 (14)0.0244 (6)
H22A−0.16920.21861.13630.029*
C23A−0.2255 (4)0.1100 (2)1.06643 (14)0.0248 (6)
H23A−0.29940.05681.08540.030*
C24A−0.1926 (4)0.0921 (2)1.00808 (14)0.0226 (6)
H24A−0.24530.02680.98770.027*
C25A−0.0808 (4)0.1710 (2)0.97943 (13)0.0199 (6)
Br1B0.53308 (4)1.14490 (3)0.211994 (15)0.03487 (9)
Br2B0.45592 (4)0.33200 (2)0.645408 (13)0.02358 (8)
Zn1B0.24696 (4)0.75184 (2)0.446619 (14)0.01731 (8)
O1B0.3972 (2)0.89302 (15)0.43195 (9)0.0201 (4)
O2B0.3728 (3)0.72934 (15)0.52202 (9)0.0233 (4)
N1B0.1589 (3)0.73430 (18)0.35485 (10)0.0177 (5)
N2B0.1568 (3)0.58417 (18)0.43259 (10)0.0170 (5)
C1B0.2168 (3)0.7995 (2)0.31420 (13)0.0189 (6)
H1BA0.17820.77800.27460.023*
C2B0.3358 (4)0.9026 (2)0.32548 (13)0.0208 (6)
C3B0.3734 (4)0.9643 (2)0.27532 (14)0.0231 (6)
H3BA0.32120.93730.23780.028*
C4B0.4852 (4)1.0630 (2)0.28103 (14)0.0247 (6)
C5B0.5651 (4)1.1055 (2)0.33632 (14)0.0252 (7)
H5BA0.63991.17340.33970.030*
C6B0.5338 (4)1.0474 (2)0.38584 (14)0.0228 (6)
H6BA0.58931.07660.42250.027*
C7B0.4187 (3)0.9434 (2)0.38308 (13)0.0193 (6)
N3B0.0443 (3)0.80924 (18)0.47850 (11)0.0201 (5)
C8B−0.0598 (4)0.8468 (2)0.44046 (14)0.0248 (6)
H8BA−0.04020.84550.40020.030*
C9B−0.1952 (4)0.8876 (3)0.45728 (16)0.0320 (7)
H9BA−0.26480.91300.42910.038*
C10B−0.2245 (4)0.8898 (3)0.51684 (16)0.0351 (8)
H10B−0.31500.91620.52970.042*
C11B−0.1174 (4)0.8521 (3)0.55712 (16)0.0342 (8)
H11B−0.13430.85310.59760.041*
C12B0.0156 (4)0.8128 (2)0.53650 (14)0.0255 (6)
H12B0.08780.78790.56390.031*
C13B0.3927 (3)0.6409 (2)0.54518 (13)0.0185 (6)
C14B0.5050 (4)0.6473 (2)0.59747 (13)0.0219 (6)
H14B0.56790.71470.61270.026*
C15B0.5248 (4)0.5578 (2)0.62670 (13)0.0217 (6)
H15B0.59870.56520.66130.026*
C16B0.4331 (4)0.4556 (2)0.60417 (13)0.0205 (6)
C17B0.3296 (3)0.4439 (2)0.55211 (13)0.0197 (6)
H17B0.27400.37530.53650.024*
C18B0.3060 (3)0.5350 (2)0.52170 (13)0.0183 (6)
C19B0.1991 (3)0.5127 (2)0.46679 (13)0.0184 (6)
H19B0.15580.44070.45440.022*
C20B0.0504 (3)0.5518 (2)0.37908 (12)0.0179 (6)
C21B−0.0534 (4)0.4481 (2)0.36509 (13)0.0193 (6)
H21B−0.05290.39410.39170.023*
C22B−0.1560 (4)0.4257 (2)0.31207 (13)0.0211 (6)
H22B−0.22260.35640.30260.025*
C23B−0.1601 (4)0.5065 (2)0.27283 (13)0.0209 (6)
H23B−0.23060.49110.23740.025*
C24B−0.0604 (4)0.6096 (2)0.28590 (13)0.0207 (6)
H24B−0.06570.66370.25970.025*
C25B0.0479 (3)0.6323 (2)0.33832 (13)0.0176 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.0529 (2)0.02217 (16)0.0329 (2)0.00699 (14)0.00489 (15)−0.00938 (13)
Br2A0.02792 (15)0.01889 (14)0.02338 (17)−0.00025 (11)−0.00122 (12)−0.00287 (11)
Zn1A0.02032 (16)0.01708 (16)0.01329 (17)0.00260 (12)0.00171 (12)−0.00011 (12)
O1A0.0240 (10)0.0184 (10)0.0180 (11)0.0039 (8)0.0038 (8)0.0005 (8)
O2A0.0251 (10)0.0206 (10)0.0157 (11)0.0004 (8)0.0028 (8)−0.0003 (8)
N1A0.0219 (12)0.0182 (12)0.0174 (13)0.0037 (9)0.0015 (9)0.0008 (10)
N2A0.0208 (12)0.0175 (11)0.0146 (12)0.0042 (9)0.0032 (9)0.0022 (9)
C1A0.0201 (14)0.0194 (14)0.0194 (15)0.0021 (11)−0.0007 (11)0.0017 (12)
C2A0.0198 (14)0.0213 (14)0.0203 (16)0.0063 (11)−0.0006 (11)−0.0010 (12)
C3A0.0231 (15)0.0199 (14)0.0246 (17)0.0040 (11)−0.0004 (12)0.0002 (12)
C4A0.0300 (16)0.0201 (14)0.0270 (17)0.0077 (12)−0.0014 (13)−0.0053 (13)
C5A0.0274 (15)0.0318 (16)0.0206 (16)0.0121 (13)0.0015 (12)−0.0067 (13)
C6A0.0230 (15)0.0271 (15)0.0218 (16)0.0070 (12)0.0057 (12)0.0008 (13)
C7A0.0183 (13)0.0213 (14)0.0176 (15)0.0064 (11)−0.0014 (11)−0.0012 (11)
N3A0.0233 (12)0.0244 (12)0.0119 (12)0.0065 (10)0.0024 (9)−0.0028 (10)
C8A0.0248 (15)0.0328 (16)0.0162 (16)0.0051 (13)0.0032 (12)−0.0027 (13)
C9A0.0249 (16)0.053 (2)0.0216 (17)0.0085 (15)0.0017 (13)−0.0084 (15)
C10A0.0373 (19)0.064 (2)0.0207 (18)0.0319 (18)0.0013 (14)−0.0004 (16)
C11A0.045 (2)0.0405 (19)0.0250 (18)0.0238 (16)0.0042 (15)0.0028 (15)
C12A0.0319 (16)0.0278 (16)0.0186 (16)0.0104 (13)0.0066 (12)−0.0013 (12)
C13A0.0181 (13)0.0206 (14)0.0200 (15)0.0070 (11)0.0006 (11)−0.0003 (12)
C14A0.0252 (15)0.0238 (15)0.0169 (15)0.0064 (12)0.0019 (11)0.0005 (12)
C15A0.0228 (14)0.0177 (14)0.0258 (17)0.0022 (11)0.0028 (12)0.0040 (12)
C16A0.0208 (14)0.0165 (13)0.0210 (16)0.0023 (11)−0.0022 (11)−0.0028 (11)
C17A0.0245 (14)0.0206 (14)0.0162 (15)0.0062 (12)0.0011 (11)−0.0011 (11)
C18A0.0218 (14)0.0172 (13)0.0181 (15)0.0068 (11)0.0007 (11)0.0007 (11)
C19A0.0211 (14)0.0210 (14)0.0153 (15)0.0062 (11)0.0025 (11)0.0003 (11)
C20A0.0190 (13)0.0220 (14)0.0182 (15)0.0049 (11)0.0021 (11)0.0031 (12)
C21A0.0258 (15)0.0219 (14)0.0174 (16)0.0045 (12)0.0034 (12)−0.0016 (12)
C22A0.0286 (15)0.0289 (16)0.0163 (15)0.0073 (13)0.0044 (12)0.0032 (12)
C23A0.0278 (15)0.0235 (15)0.0241 (17)0.0049 (12)0.0094 (12)0.0073 (13)
C24A0.0262 (15)0.0186 (14)0.0224 (16)0.0035 (12)0.0032 (12)0.0017 (12)
C25A0.0243 (14)0.0206 (14)0.0155 (15)0.0071 (11)0.0010 (11)0.0011 (11)
Br1B0.03360 (17)0.03722 (18)0.03095 (19)−0.00047 (14)0.00568 (13)0.01775 (14)
Br2B0.02856 (15)0.02544 (15)0.01949 (16)0.01116 (12)0.00222 (11)0.00614 (12)
Zn1B0.02121 (16)0.01680 (15)0.01404 (17)0.00474 (12)0.00144 (12)0.00084 (12)
O1B0.0243 (10)0.0202 (10)0.0150 (11)0.0031 (8)0.0033 (8)0.0015 (8)
O2B0.0294 (11)0.0205 (10)0.0187 (11)0.0052 (8)−0.0036 (8)0.0015 (8)
N1B0.0195 (11)0.0181 (11)0.0168 (13)0.0069 (9)0.0028 (9)0.0008 (10)
N2B0.0191 (11)0.0190 (11)0.0133 (12)0.0046 (9)0.0025 (9)0.0014 (9)
C1B0.0216 (14)0.0228 (14)0.0140 (14)0.0088 (11)0.0006 (11)0.0002 (12)
C2B0.0195 (14)0.0208 (14)0.0241 (16)0.0079 (11)0.0037 (11)0.0026 (12)
C3B0.0243 (15)0.0273 (15)0.0183 (16)0.0068 (12)0.0030 (12)0.0042 (12)
C4B0.0251 (15)0.0246 (15)0.0265 (17)0.0066 (12)0.0094 (12)0.0122 (13)
C5B0.0252 (15)0.0189 (14)0.0318 (18)0.0045 (12)0.0070 (13)0.0025 (13)
C6B0.0239 (15)0.0217 (14)0.0225 (16)0.0049 (12)0.0027 (12)−0.0017 (12)
C7B0.0181 (13)0.0213 (14)0.0208 (16)0.0083 (11)0.0046 (11)0.0011 (12)
N3B0.0227 (12)0.0174 (11)0.0200 (14)0.0038 (9)0.0030 (10)−0.0003 (10)
C8B0.0261 (15)0.0272 (15)0.0230 (17)0.0102 (12)0.0030 (12)−0.0016 (13)
C9B0.0271 (16)0.0330 (17)0.037 (2)0.0107 (14)−0.0018 (14)−0.0052 (15)
C10B0.0239 (16)0.0386 (18)0.042 (2)0.0060 (14)0.0077 (14)−0.0124 (16)
C11B0.0331 (18)0.0391 (18)0.0264 (19)−0.0011 (14)0.0135 (14)−0.0080 (15)
C12B0.0295 (16)0.0246 (15)0.0201 (17)0.0016 (12)0.0036 (12)−0.0007 (12)
C13B0.0199 (14)0.0214 (14)0.0152 (15)0.0058 (11)0.0047 (11)0.0006 (11)
C14B0.0214 (14)0.0240 (15)0.0191 (16)0.0036 (12)0.0020 (11)−0.0018 (12)
C15B0.0229 (14)0.0278 (15)0.0153 (15)0.0080 (12)0.0014 (11)0.0002 (12)
C16B0.0208 (14)0.0253 (15)0.0181 (15)0.0093 (12)0.0060 (11)0.0055 (12)
C17B0.0205 (14)0.0209 (14)0.0193 (15)0.0064 (11)0.0060 (11)0.0013 (11)
C18B0.0199 (13)0.0212 (14)0.0153 (15)0.0074 (11)0.0043 (11)0.0016 (11)
C19B0.0200 (13)0.0174 (13)0.0175 (15)0.0028 (11)0.0046 (11)0.0009 (11)
C20B0.0197 (13)0.0214 (14)0.0136 (14)0.0069 (11)0.0039 (11)−0.0013 (11)
C21B0.0231 (14)0.0192 (14)0.0162 (15)0.0057 (11)0.0036 (11)0.0011 (11)
C22B0.0213 (14)0.0202 (14)0.0209 (16)0.0036 (11)0.0028 (11)−0.0018 (12)
C23B0.0205 (14)0.0271 (15)0.0148 (15)0.0062 (12)0.0003 (11)−0.0029 (12)
C24B0.0229 (14)0.0251 (15)0.0160 (15)0.0088 (12)0.0033 (11)0.0032 (12)
C25B0.0182 (13)0.0185 (13)0.0174 (15)0.0056 (11)0.0069 (11)0.0005 (11)
Geometric parameters (Å, °) top
Br1A—C4A1.905 (3)Br1B—C4B1.914 (3)
Br2A—C16A1.901 (3)Br2B—C16B1.899 (3)
Zn1A—O1A1.9656 (19)Zn1B—O2B1.973 (2)
Zn1A—O2A1.979 (2)Zn1B—O1B1.9757 (19)
Zn1A—N2A2.082 (2)Zn1B—N3B2.096 (2)
Zn1A—N3A2.092 (2)Zn1B—N2B2.101 (2)
Zn1A—N1A2.114 (2)Zn1B—N1B2.117 (2)
O1A—C7A1.296 (3)O1B—C7B1.295 (4)
O2A—C13A1.302 (3)O2B—C13B1.299 (3)
N1A—C1A1.290 (4)N1B—C1B1.297 (4)
N1A—C25A1.417 (4)N1B—C25B1.417 (4)
N2A—C19A1.297 (4)N2B—C19B1.303 (4)
N2A—C20A1.410 (4)N2B—C20B1.413 (4)
C1A—C2A1.433 (4)C1B—C2B1.437 (4)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.412 (4)C2B—C3B1.409 (4)
C2A—C7A1.432 (4)C2B—C7B1.433 (4)
C3A—C4A1.363 (4)C3B—C4B1.363 (4)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.395 (5)C4B—C5B1.387 (5)
C5A—C6A1.364 (4)C5B—C6B1.366 (4)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.423 (4)C6B—C7B1.427 (4)
C6A—H6AA0.9300C6B—H6BA0.9300
N3A—C8A1.339 (4)N3B—C8B1.331 (4)
N3A—C12A1.343 (4)N3B—C12B1.341 (4)
C8A—C9A1.386 (4)C8B—C9B1.382 (4)
C8A—H8AA0.9300C8B—H8BA0.9300
C9A—C10A1.380 (5)C9B—C10B1.377 (5)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—C11A1.376 (5)C10B—C11B1.379 (5)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.379 (5)C11B—C12B1.383 (5)
C11A—H11A0.9300C11B—H11B0.9300
C12A—H12A0.9300C12B—H12B0.9300
C13A—C18A1.423 (4)C13B—C14B1.415 (4)
C13A—C14A1.423 (4)C13B—C18B1.433 (4)
C14A—C15A1.370 (4)C14B—C15B1.375 (4)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.393 (4)C15B—C16B1.397 (4)
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.360 (4)C16B—C17B1.367 (4)
C17A—C18A1.411 (4)C17B—C18B1.415 (4)
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.438 (4)C18B—C19B1.430 (4)
C19A—H19A0.9300C19B—H19B0.9300
C20A—C21A1.400 (4)C20B—C21B1.403 (4)
C20A—C25A1.407 (4)C20B—C25B1.404 (4)
C21A—C22A1.377 (4)C21B—C22B1.379 (4)
C21A—H21A0.9300C21B—H21B0.9300
C22A—C23A1.383 (4)C22B—C23B1.386 (4)
C22A—H22A0.9300C22B—H22B0.9300
C23A—C24A1.379 (4)C23B—C24B1.382 (4)
C23A—H23A0.9300C23B—H23B0.9300
C24A—C25A1.394 (4)C24B—C25B1.391 (4)
C24A—H24A0.9300C24B—H24B0.9300
O1A—Zn1A—O2A94.05 (8)O2B—Zn1B—O1B96.53 (8)
O1A—Zn1A—N2A151.54 (8)O2B—Zn1B—N3B101.28 (9)
O2A—Zn1A—N2A90.27 (9)O1B—Zn1B—N3B97.35 (8)
O1A—Zn1A—N3A102.03 (8)O2B—Zn1B—N2B89.32 (8)
O2A—Zn1A—N3A99.03 (9)O1B—Zn1B—N2B153.76 (8)
N2A—Zn1A—N3A105.04 (9)N3B—Zn1B—N2B106.58 (9)
O1A—Zn1A—N1A89.02 (9)O2B—Zn1B—N1B159.18 (8)
O2A—Zn1A—N1A160.97 (9)O1B—Zn1B—N1B88.92 (8)
N2A—Zn1A—N1A78.44 (9)N3B—Zn1B—N1B97.91 (9)
N3A—Zn1A—N1A98.68 (9)N2B—Zn1B—N1B77.45 (9)
C7A—O1A—Zn1A129.87 (18)C7B—O1B—Zn1B130.36 (18)
C13A—O2A—Zn1A129.37 (19)C13B—O2B—Zn1B130.36 (18)
C1A—N1A—C25A121.8 (2)C1B—N1B—C25B120.2 (2)
C1A—N1A—Zn1A125.4 (2)C1B—N1B—Zn1B125.86 (19)
C25A—N1A—Zn1A112.53 (17)C25B—N1B—Zn1B113.05 (18)
C19A—N2A—C20A121.2 (2)C19B—N2B—C20B120.5 (2)
C19A—N2A—Zn1A125.0 (2)C19B—N2B—Zn1B125.38 (19)
C20A—N2A—Zn1A113.81 (18)C20B—N2B—Zn1B113.97 (17)
N1A—C1A—C2A125.6 (3)N1B—C1B—C2B125.1 (3)
N1A—C1A—H1AA117.2N1B—C1B—H1BA117.4
C2A—C1A—H1AA117.2C2B—C1B—H1BA117.4
C3A—C2A—C7A119.4 (3)C3B—C2B—C7B119.5 (3)
C3A—C2A—C1A116.5 (3)C3B—C2B—C1B116.1 (3)
C7A—C2A—C1A124.1 (3)C7B—C2B—C1B124.3 (3)
C4A—C3A—C2A120.9 (3)C4B—C3B—C2B120.9 (3)
C4A—C3A—H3AA119.6C4B—C3B—H3BA119.6
C2A—C3A—H3AA119.6C2B—C3B—H3BA119.6
C3A—C4A—C5A120.8 (3)C3B—C4B—C5B120.9 (3)
C3A—C4A—Br1A120.1 (2)C3B—C4B—Br1B119.8 (2)
C5A—C4A—Br1A119.2 (2)C5B—C4B—Br1B119.3 (2)
C6A—C5A—C4A119.8 (3)C6B—C5B—C4B119.9 (3)
C6A—C5A—H5AA120.1C6B—C5B—H5BA120.0
C4A—C5A—H5AA120.1C4B—C5B—H5BA120.0
C5A—C6A—C7A122.2 (3)C5B—C6B—C7B122.1 (3)
C5A—C6A—H6AA118.9C5B—C6B—H6BA118.9
C7A—C6A—H6AA118.9C7B—C6B—H6BA118.9
O1A—C7A—C6A118.4 (3)O1B—C7B—C6B118.4 (3)
O1A—C7A—C2A124.7 (3)O1B—C7B—C2B125.0 (3)
C6A—C7A—C2A116.9 (3)C6B—C7B—C2B116.6 (3)
C8A—N3A—C12A117.9 (3)C8B—N3B—C12B117.4 (3)
C8A—N3A—Zn1A121.9 (2)C8B—N3B—Zn1B119.6 (2)
C12A—N3A—Zn1A120.1 (2)C12B—N3B—Zn1B123.0 (2)
N3A—C8A—C9A122.9 (3)N3B—C8B—C9B123.8 (3)
N3A—C8A—H8AA118.5N3B—C8B—H8BA118.1
C9A—C8A—H8AA118.5C9B—C8B—H8BA118.1
C10A—C9A—C8A118.1 (3)C10B—C9B—C8B118.3 (3)
C10A—C9A—H9AA120.9C10B—C9B—H9BA120.9
C8A—C9A—H9AA120.9C8B—C9B—H9BA120.9
C11A—C10A—C9A119.6 (3)C9B—C10B—C11B118.9 (3)
C11A—C10A—H10A120.2C9B—C10B—H10B120.6
C9A—C10A—H10A120.2C11B—C10B—H10B120.6
C10A—C11A—C12A118.7 (3)C10B—C11B—C12B119.1 (3)
C10A—C11A—H11A120.6C10B—C11B—H11B120.4
C12A—C11A—H11A120.6C12B—C11B—H11B120.4
N3A—C12A—C11A122.6 (3)N3B—C12B—C11B122.5 (3)
N3A—C12A—H12A118.7N3B—C12B—H12B118.7
C11A—C12A—H12A118.7C11B—C12B—H12B118.7
O2A—C13A—C18A124.5 (3)O2B—C13B—C14B119.2 (2)
O2A—C13A—C14A118.8 (3)O2B—C13B—C18B124.3 (2)
C18A—C13A—C14A116.7 (3)C14B—C13B—C18B116.5 (3)
C15A—C14A—C13A122.3 (3)C15B—C14B—C13B122.6 (3)
C15A—C14A—H14A118.8C15B—C14B—H14B118.7
C13A—C14A—H14A118.8C13B—C14B—H14B118.7
C14A—C15A—C16A119.5 (3)C14B—C15B—C16B119.6 (3)
C14A—C15A—H15A120.3C14B—C15B—H15B120.2
C16A—C15A—H15A120.3C16B—C15B—H15B120.2
C17A—C16A—C15A120.8 (3)C17B—C16B—C15B120.5 (3)
C17A—C16A—Br2A119.8 (2)C17B—C16B—Br2B119.7 (2)
C15A—C16A—Br2A119.4 (2)C15B—C16B—Br2B119.8 (2)
C16A—C17A—C18A120.8 (3)C16B—C17B—C18B120.7 (3)
C16A—C17A—H17A119.6C16B—C17B—H17B119.6
C18A—C17A—H17A119.6C18B—C17B—H17B119.6
C17A—C18A—C13A119.8 (3)C17B—C18B—C19B115.7 (2)
C17A—C18A—C19A115.6 (3)C17B—C18B—C13B119.9 (3)
C13A—C18A—C19A124.6 (3)C19B—C18B—C13B124.3 (3)
N2A—C19A—C18A126.1 (3)N2B—C19B—C18B125.9 (3)
N2A—C19A—H19A117.0N2B—C19B—H19B117.1
C18A—C19A—H19A117.0C18B—C19B—H19B117.1
C21A—C20A—C25A118.7 (3)C21B—C20B—C25B119.0 (3)
C21A—C20A—N2A124.7 (3)C21B—C20B—N2B125.0 (3)
C25A—C20A—N2A116.5 (3)C25B—C20B—N2B115.9 (2)
C22A—C21A—C20A120.5 (3)C22B—C21B—C20B120.4 (3)
C22A—C21A—H21A119.7C22B—C21B—H21B119.8
C20A—C21A—H21A119.7C20B—C21B—H21B119.8
C21A—C22A—C23A120.6 (3)C21B—C22B—C23B120.1 (3)
C21A—C22A—H22A119.7C21B—C22B—H22B120.0
C23A—C22A—H22A119.7C23B—C22B—H22B120.0
C24A—C23A—C22A119.9 (3)C24B—C23B—C22B120.7 (3)
C24A—C23A—H23A120.0C24B—C23B—H23B119.7
C22A—C23A—H23A120.0C22B—C23B—H23B119.7
C23A—C24A—C25A120.5 (3)C23B—C24B—C25B119.8 (3)
C23A—C24A—H24A119.8C23B—C24B—H24B120.1
C25A—C24A—H24A119.8C25B—C24B—H24B120.1
C24A—C25A—C20A119.7 (3)C24B—C25B—C20B120.1 (3)
C24A—C25A—N1A124.5 (3)C24B—C25B—N1B124.1 (3)
C20A—C25A—N1A115.8 (3)C20B—C25B—N1B115.8 (2)
O2A—Zn1A—O1A—C7A173.0 (2)O2B—Zn1B—O1B—C7B159.8 (2)
N2A—Zn1A—O1A—C7A75.0 (3)N3B—Zn1B—O1B—C7B−97.9 (2)
N3A—Zn1A—O1A—C7A−86.8 (2)N2B—Zn1B—O1B—C7B57.9 (3)
N1A—Zn1A—O1A—C7A11.8 (2)N1B—Zn1B—O1B—C7B−0.1 (2)
O1A—Zn1A—O2A—C13A−154.9 (2)O1B—Zn1B—O2B—C13B−149.2 (2)
N2A—Zn1A—O2A—C13A−3.0 (2)N3B—Zn1B—O2B—C13B112.0 (2)
N3A—Zn1A—O2A—C13A102.3 (2)N2B—Zn1B—O2B—C13B5.2 (2)
N1A—Zn1A—O2A—C13A−56.1 (4)N1B—Zn1B—O2B—C13B−44.9 (4)
O1A—Zn1A—N1A—C1A−4.4 (2)O2B—Zn1B—N1B—C1B−100.5 (3)
O2A—Zn1A—N1A—C1A−104.1 (3)O1B—Zn1B—N1B—C1B5.2 (2)
N2A—Zn1A—N1A—C1A−158.7 (2)N3B—Zn1B—N1B—C1B102.5 (2)
N3A—Zn1A—N1A—C1A97.6 (2)N2B—Zn1B—N1B—C1B−152.2 (2)
O1A—Zn1A—N1A—C25A169.47 (18)O2B—Zn1B—N1B—C25B68.9 (3)
O2A—Zn1A—N1A—C25A69.9 (3)O1B—Zn1B—N1B—C25B174.53 (17)
N2A—Zn1A—N1A—C25A15.18 (18)N3B—Zn1B—N1B—C25B−88.20 (18)
N3A—Zn1A—N1A—C25A−88.51 (19)N2B—Zn1B—N1B—C25B17.12 (17)
O1A—Zn1A—N2A—C19A99.7 (3)O2B—Zn1B—N2B—C19B−3.4 (2)
O2A—Zn1A—N2A—C19A0.7 (2)O1B—Zn1B—N2B—C19B100.1 (3)
N3A—Zn1A—N2A—C19A−98.7 (2)N3B—Zn1B—N2B—C19B−104.9 (2)
N1A—Zn1A—N2A—C19A165.3 (2)N1B—Zn1B—N2B—C19B160.4 (2)
O1A—Zn1A—N2A—C20A−79.2 (3)O2B—Zn1B—N2B—C20B−179.50 (19)
O2A—Zn1A—N2A—C20A−178.21 (18)O1B—Zn1B—N2B—C20B−76.0 (3)
N3A—Zn1A—N2A—C20A82.37 (19)N3B—Zn1B—N2B—C20B78.93 (19)
N1A—Zn1A—N2A—C20A−13.64 (18)N1B—Zn1B—N2B—C20B−15.71 (18)
C25A—N1A—C1A—C2A−177.5 (3)C25B—N1B—C1B—C2B−177.0 (2)
Zn1A—N1A—C1A—C2A−4.1 (4)Zn1B—N1B—C1B—C2B−8.4 (4)
N1A—C1A—C2A—C3A−173.0 (3)N1B—C1B—C2B—C3B−175.8 (3)
N1A—C1A—C2A—C7A9.2 (4)N1B—C1B—C2B—C7B5.7 (4)
C7A—C2A—C3A—C4A−0.5 (4)C7B—C2B—C3B—C4B−1.2 (4)
C1A—C2A—C3A—C4A−178.4 (3)C1B—C2B—C3B—C4B−179.7 (3)
C2A—C3A—C4A—C5A1.2 (4)C2B—C3B—C4B—C5B0.0 (4)
C2A—C3A—C4A—Br1A179.7 (2)C2B—C3B—C4B—Br1B−179.9 (2)
C3A—C4A—C5A—C6A−0.4 (4)C3B—C4B—C5B—C6B0.9 (4)
Br1A—C4A—C5A—C6A−178.9 (2)Br1B—C4B—C5B—C6B−179.2 (2)
C4A—C5A—C6A—C7A−1.2 (4)C4B—C5B—C6B—C7B−0.7 (4)
Zn1A—O1A—C7A—C6A170.82 (19)Zn1B—O1B—C7B—C6B178.19 (18)
Zn1A—O1A—C7A—C2A−10.8 (4)Zn1B—O1B—C7B—C2B−2.1 (4)
C5A—C6A—C7A—O1A−179.7 (3)C5B—C6B—C7B—O1B179.3 (3)
C5A—C6A—C7A—C2A1.8 (4)C5B—C6B—C7B—C2B−0.4 (4)
C3A—C2A—C7A—O1A−179.3 (3)C3B—C2B—C7B—O1B−178.4 (3)
C1A—C2A—C7A—O1A−1.7 (4)C1B—C2B—C7B—O1B0.0 (4)
C3A—C2A—C7A—C6A−0.9 (4)C3B—C2B—C7B—C6B1.3 (4)
C1A—C2A—C7A—C6A176.8 (3)C1B—C2B—C7B—C6B179.8 (3)
O1A—Zn1A—N3A—C8A78.5 (2)O2B—Zn1B—N3B—C8B171.8 (2)
O2A—Zn1A—N3A—C8A174.6 (2)O1B—Zn1B—N3B—C8B73.6 (2)
N2A—Zn1A—N3A—C8A−92.7 (2)N2B—Zn1B—N3B—C8B−95.6 (2)
N1A—Zn1A—N3A—C8A−12.4 (2)N1B—Zn1B—N3B—C8B−16.4 (2)
O1A—Zn1A—N3A—C12A−99.1 (2)O2B—Zn1B—N3B—C12B−6.5 (2)
O2A—Zn1A—N3A—C12A−2.9 (2)O1B—Zn1B—N3B—C12B−104.7 (2)
N2A—Zn1A—N3A—C12A89.8 (2)N2B—Zn1B—N3B—C12B86.2 (2)
N1A—Zn1A—N3A—C12A170.1 (2)N1B—Zn1B—N3B—C12B165.4 (2)
C12A—N3A—C8A—C9A0.0 (4)C12B—N3B—C8B—C9B−0.8 (4)
Zn1A—N3A—C8A—C9A−177.6 (2)Zn1B—N3B—C8B—C9B−179.1 (2)
N3A—C8A—C9A—C10A−0.5 (5)N3B—C8B—C9B—C10B0.1 (5)
C8A—C9A—C10A—C11A0.5 (5)C8B—C9B—C10B—C11B0.5 (5)
C9A—C10A—C11A—C12A0.0 (5)C9B—C10B—C11B—C12B−0.3 (5)
C8A—N3A—C12A—C11A0.5 (4)C8B—N3B—C12B—C11B0.9 (4)
Zn1A—N3A—C12A—C11A178.2 (2)Zn1B—N3B—C12B—C11B179.2 (2)
C10A—C11A—C12A—N3A−0.5 (5)C10B—C11B—C12B—N3B−0.4 (5)
Zn1A—O2A—C13A—C18A2.0 (4)Zn1B—O2B—C13B—C14B173.5 (2)
Zn1A—O2A—C13A—C14A−178.32 (18)Zn1B—O2B—C13B—C18B−7.3 (4)
O2A—C13A—C14A—C15A179.2 (3)O2B—C13B—C14B—C15B175.9 (3)
C18A—C13A—C14A—C15A−1.1 (4)C18B—C13B—C14B—C15B−3.4 (4)
C13A—C14A—C15A—C16A0.3 (4)C13B—C14B—C15B—C16B0.8 (4)
C14A—C15A—C16A—C17A0.9 (4)C14B—C15B—C16B—C17B2.6 (4)
C14A—C15A—C16A—Br2A179.9 (2)C14B—C15B—C16B—Br2B−178.5 (2)
C15A—C16A—C17A—C18A−1.3 (4)C15B—C16B—C17B—C18B−3.4 (4)
Br2A—C16A—C17A—C18A179.7 (2)Br2B—C16B—C17B—C18B177.8 (2)
C16A—C17A—C18A—C13A0.4 (4)C16B—C17B—C18B—C19B178.2 (3)
C16A—C17A—C18A—C19A178.7 (3)C16B—C17B—C18B—C13B0.7 (4)
O2A—C13A—C18A—C17A−179.6 (2)O2B—C13B—C18B—C17B−176.6 (3)
C14A—C13A—C18A—C17A0.7 (4)C14B—C13B—C18B—C17B2.6 (4)
O2A—C13A—C18A—C19A2.3 (4)O2B—C13B—C18B—C19B6.1 (4)
C14A—C13A—C18A—C19A−177.4 (3)C14B—C13B—C18B—C19B−174.7 (3)
C20A—N2A—C19A—C18A−178.5 (3)C20B—N2B—C19B—C18B179.8 (3)
Zn1A—N2A—C19A—C18A2.7 (4)Zn1B—N2B—C19B—C18B3.8 (4)
C17A—C18A—C19A—N2A177.0 (3)C17B—C18B—C19B—N2B178.1 (3)
C13A—C18A—C19A—N2A−4.8 (4)C13B—C18B—C19B—N2B−4.5 (5)
C19A—N2A—C20A—C21A13.7 (4)C19B—N2B—C20B—C21B17.3 (4)
Zn1A—N2A—C20A—C21A−167.3 (2)Zn1B—N2B—C20B—C21B−166.3 (2)
C19A—N2A—C20A—C25A−168.8 (2)C19B—N2B—C20B—C25B−164.3 (2)
Zn1A—N2A—C20A—C25A10.1 (3)Zn1B—N2B—C20B—C25B12.0 (3)
C25A—C20A—C21A—C22A−0.3 (4)C25B—C20B—C21B—C22B0.0 (4)
N2A—C20A—C21A—C22A177.1 (3)N2B—C20B—C21B—C22B178.4 (3)
C20A—C21A—C22A—C23A−1.4 (4)C20B—C21B—C22B—C23B−1.5 (4)
C21A—C22A—C23A—C24A1.2 (4)C21B—C22B—C23B—C24B0.8 (4)
C22A—C23A—C24A—C25A0.6 (4)C22B—C23B—C24B—C25B1.3 (4)
C23A—C24A—C25A—C20A−2.2 (4)C23B—C24B—C25B—C20B−2.8 (4)
C23A—C24A—C25A—N1A179.1 (3)C23B—C24B—C25B—N1B177.9 (2)
C21A—C20A—C25A—C24A2.0 (4)C21B—C20B—C25B—C24B2.1 (4)
N2A—C20A—C25A—C24A−175.5 (2)N2B—C20B—C25B—C24B−176.4 (2)
C21A—C20A—C25A—N1A−179.2 (2)C21B—C20B—C25B—N1B−178.6 (2)
N2A—C20A—C25A—N1A3.2 (4)N2B—C20B—C25B—N1B3.0 (3)
C1A—N1A—C25A—C24A−21.8 (4)C1B—N1B—C25B—C24B−27.0 (4)
Zn1A—N1A—C25A—C24A164.1 (2)Zn1B—N1B—C25B—C24B163.0 (2)
C1A—N1A—C25A—C20A159.5 (3)C1B—N1B—C25B—C20B153.7 (2)
Zn1A—N1A—C25A—C20A−14.7 (3)Zn1B—N1B—C25B—C20B−16.3 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C9A—H9AA···O1Ai0.932.443.233 (4)143
C8B—H8BA···N1B0.932.613.216 (4)123
C12A—H12A···O2A0.932.603.178 (4)121
C24B—H24B···O1Aii0.932.363.267 (3)166
C17A—H17A···Cg1iii0.932.893.820 (3)174
C17B—H17B···Cg2ii0.932.963.882 (3)173
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1; (iii) −x, −y+1, −z+2.
Table 1
Selected geometric parameters (Å, °) top
Zn1A—O1A1.9656 (19)Zn1B—O2B1.973 (2)
Zn1A—O2A1.979 (2)Zn1B—O1B1.9757 (19)
Zn1A—N2A2.082 (2)Zn1B—N3B2.096 (2)
Zn1A—N3A2.092 (2)Zn1B—N2B2.101 (2)
Zn1A—N1A2.114 (2)Zn1B—N1B2.117 (2)
O1A—Zn1A—O2A94.05 (8)O2B—Zn1B—O1B96.53 (8)
O1A—Zn1A—N2A151.54 (8)O2B—Zn1B—N3B101.28 (9)
O2A—Zn1A—N2A90.27 (9)O1B—Zn1B—N3B97.35 (8)
O1A—Zn1A—N3A102.03 (8)O2B—Zn1B—N2B89.32 (8)
O2A—Zn1A—N3A99.03 (9)O1B—Zn1B—N2B153.76 (8)
N2A—Zn1A—N3A105.04 (9)N3B—Zn1B—N2B106.58 (9)
O1A—Zn1A—N1A89.02 (9)O2B—Zn1B—N1B159.18 (8)
O2A—Zn1A—N1A160.97 (9)O1B—Zn1B—N1B88.92 (8)
N2A—Zn1A—N1A78.44 (9)N3B—Zn1B—N1B97.91 (9)
N3A—Zn1A—N1A98.68 (9)N2B—Zn1B—N1B77.45 (9)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C9A—H9AA···O1Ai0.932.443.233 (4)143
C8B—H8BA···N1B0.932.613.216 (4)123
C12A—H12A···O2A0.932.603.178 (4)121
C24B—H24B···O1Aii0.932.363.267 (3)166
C17A—H17A···Cg1iii0.932.893.820 (3)174
C17B—H17B···Cg2ii0.932.963.882 (3)173
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1; (iii) −x, −y+1, −z+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
References top

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.

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.

Bruker (2005). APEX2 (Version 1.27), SAINT (Version 7.12a) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.

Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Ibrahim, K. (2007). Acta Cryst. E63, m1633–m1634.

Eltayeb, N. E., Teoh, S. G., Ng, S.-L., Fun, H.-K. & Ibrahim, K. (2007). Acta Cryst. E63, m1284–m1285.

Sheldrick, G. M. (1998). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.