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Acta Cryst. (2007). E63, m1672-m1673    [ doi:10.1107/S1600536807022829 ]

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

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

Abstract top

There are two unique molecules of the title mononuclear zinc(II) complex, [Zn(C20H12Cl2N2O2)(C5H5N)], in the asymmetric unit. The ZnII ion is five-coordinate in a distorted square-pyramidal geometry, with the basal plane defined by the two N and two O atoms of the Schiff base ligand and the apical position occupied by the N atom of the pyridine. The N and O atoms of the Schiff base ligand are mutually cis. The molecules are linked by weak C-H...Cl interactions into chains along the b axis. Other molecules are arranged diagonally between adjacent chains and bridge the chains through weak C-H...O interactions. The crystal structure is further stabilized by weak intra- and intermolecular C-H...O hydrogen bonds and C-H...[pi] interactions.

Comment top

Schiff base ligands have played an important role in the development of coordination chemistry as they readily form stable complexes with most transition metal ions (Pal et al., 2005). It is also well known that zinc complexes with Schiff-bases are important in biological systems and coordination chemistry (Collinson & Fenton, 1996; Tarafder, Chew et al., 2002; Tarafder, Jin et al., 2002). Recently, we reported the crystal structure of aqua{2,2'-[1,2-phenylenebis(nitrilomethylidyne)]bis(4-methoxyphenolato)- κ4O,O',N,N'}zinc(II), (II), derived from a related Schiff base ligand (Eltayeb et al., 2007). As an extension of our investigations of the structure of Schiff base zinc(II) complexes, the title mononuclear zinc(II) complex, (I) is reported here.

Complex (I) is a mononuclear zinc(II) compound (Fig. 1). There are two unique molecules in the asymmetric unit. Each ZnII ion is in a distorted square pyramidal geometry and five-coordinated by two N and two O atoms of a Schiff-base ligand forming the basal plane, and by the N atom of pyridine at the axial position. The bond lengths and angles are within normal ranges (Allen et al., 1987) and comparable to the values in another closely related zinc(II) complex, (II) (Eltayeb et al., 2007). The bond angles around the central metal zinc(II) show some deviation from ideal square pyramidal geometry. The dihedral angles between the pyridine (C21–C25/N3) and C1–C6 or C15–C20 rings are 89.75 (11)° and 74.44 (10)°, respectively in molecule A [88.32 (10)Å and 75.71 (10)° in molecule B].

In the crystal structure of (I) as shown Fig. 2, adjacent molecules are linked through weak C—H···Cl interactions into chains running along the b axis. Between the adjacent chains, there are molecules which are arranged diagonally and are bridging these chains through weak C—H···O interactions. The crystal is stabilized by weak C—H···O intra- and intermolecular interactions (Table 1). C—H···π were also observed; Cg1, Cg2 and Cg3 are the centroids of Zn1A–O1A–C1A–C6A–C7A–N1A, Zn1B–O1B–C1B–C6B–C7B–N1B and C1A–C6A, respectively (Table 1).

Related literature top

For a background to Schiff base coordination complexes, see: Pal et al. (2005); Collinson & Fenton (1996); Tarafder, Chew et al. (2002); Tarafder, Jin et al. (2002). For related literature on values of bond lengths and angles, see: Allen et al. (1987). For related structures, see for example: Humphrey et al. (1999); Eltayeb et al. (2007).

Experimental top

The title compound (I) was synthesized by adding 5-chloro-2-hydroxybenzaldehyde (0.624 g, 4 mmol) to a solution of o-phenylenediamine (0.216 g, 2 mmol) in 95% ethanol (20 ml). 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. A yellow precipitate was obtained, washed with about 5 ml e thanol, dried, and then washed by a copious amount of diethyl ether. This precipitate was then dissolved in 20 ml of pyridine. Yellow single crystals of (I) suitable for x-ray structure determination formed after several days of slow evaporation of the pyridine at room temperature.

Refinement top

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.96 Å. The Uiso values were constrained to be 1.2Ueq of the carrier atoms. The highest residual peak is located 1.17 Å from Cl1B and the deepest hole is located 0.73 Å from Zn1A.

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 (I), showing 60% probability displacement ellipsoids and the atomic numbering.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the a axis. Hydrogen bonds are shown as dashed lines.
{4,4'-Dichloro-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenolato- κ4O,N,N',O'}(pyridine-κN)zinc(II) top
Crystal data top
[Zn(C20H12Cl2N2O2)(C5H5N)]Z = 4
Mr = 527.71F(000) = 1072
Triclinic, P1Dx = 1.606 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9840 (4) ÅCell parameters from 15712 reflections
b = 12.6632 (6) Åθ = 0.9–32.5°
c = 22.3163 (11) ŵ = 1.40 mm−1
α = 91.574 (3)°T = 100 K
β = 94.154 (3)°Needle, yellow
γ = 103.791 (3)°0.60 × 0.20 × 0.12 mm
V = 2183.11 (19) Å3
Data collection top
Bruker SMART APEX II CCD area-detector
diffractometer		15712 independent reflections
Radiation source: fine-focus sealed tube12030 reflections with I > 2σ(I)
graphiteRint = 0.060
Detector resolution: 8.33 pixels mm-1θmax = 32.5°, θmin = 0.9°
ω scansh = −11→12
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −19→19
Tmin = 0.489, Tmax = 0.855l = −33→33
55655 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0438P)2 + 1.047P]
where P = (Fo2 + 2Fc2)/3
15712 reflections(Δ/σ)max = 0.001
595 parametersΔρmax = 0.59 e Å−3
0 restraintsΔρmin = −0.67 e Å−3
Crystal data top
[Zn(C20H12Cl2N2O2)(C5H5N)]γ = 103.791 (3)°
Mr = 527.71V = 2183.11 (19) Å3
Triclinic, P1Z = 4
a = 7.9840 (4) ÅMo Kα radiation
b = 12.6632 (6) ŵ = 1.40 mm−1
c = 22.3163 (11) ÅT = 100 K
α = 91.574 (3)°0.60 × 0.20 × 0.12 mm
β = 94.154 (3)°
Data collection top
Bruker SMART APEX II CCD area-detector
diffractometer		15712 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		12030 reflections with I > 2σ(I)
Tmin = 0.489, Tmax = 0.855Rint = 0.060
55655 measured reflectionsθmax = 32.5°
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.111Δρmax = 0.59 e Å−3
S = 1.07Δρmin = −0.67 e Å−3
15712 reflectionsAbsolute structure: ?
595 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Zn1A0.07617 (3)0.304165 (17)0.886205 (10)0.01428 (5)
Cl1A−0.08004 (10)−0.22912 (5)0.72552 (3)0.03907 (15)
Cl2A0.60377 (7)0.80907 (4)1.03804 (2)0.02316 (10)
O1A0.13688 (18)0.22551 (11)0.81699 (6)0.0176 (3)
O2A0.24672 (18)0.44173 (11)0.87359 (6)0.0183 (3)
N1A−0.0384 (2)0.15259 (13)0.92090 (7)0.0168 (3)
N2A0.0915 (2)0.34531 (13)0.97772 (7)0.0150 (3)
N3A−0.1483 (2)0.34607 (14)0.85123 (7)0.0179 (3)
C1A0.0853 (2)0.12367 (15)0.79939 (9)0.0165 (3)
C2A0.1296 (3)0.09106 (17)0.74236 (9)0.0209 (4)
H2AB0.19530.14310.71940.025*
C3A0.0783 (3)−0.01512 (18)0.72002 (10)0.0249 (4)
H3AB0.1075−0.03370.68220.030*
C4A−0.0174 (3)−0.09444 (17)0.75420 (10)0.0250 (4)
C5A−0.0601 (3)−0.06862 (16)0.81019 (10)0.0222 (4)
H5AB−0.1221−0.12300.83270.027*
C6A−0.0108 (2)0.03992 (15)0.83404 (9)0.0178 (3)
C7A−0.0575 (2)0.05834 (15)0.89393 (9)0.0179 (3)
H7AB−0.1052−0.00260.91490.021*
C8A−0.0853 (2)0.16341 (15)0.98018 (9)0.0166 (3)
C9A−0.2003 (3)0.08306 (16)1.00863 (10)0.0215 (4)
H9AB−0.25160.01700.98810.026*
C10A−0.2384 (3)0.10095 (18)1.06700 (10)0.0237 (4)
H10A−0.31460.04681.08560.028*
C11A−0.1638 (3)0.19910 (18)1.09781 (9)0.0220 (4)
H11A−0.18720.21001.13740.026*
C12A−0.0538 (3)0.28133 (16)1.06969 (9)0.0194 (4)
H12A−0.00670.34791.09020.023*
C13A−0.0133 (2)0.26499 (15)1.01086 (9)0.0158 (3)
C14A0.1872 (2)0.43397 (15)1.00396 (9)0.0161 (3)
H14A0.18560.44171.04550.019*
C15A0.2958 (2)0.52160 (15)0.97474 (8)0.0153 (3)
C16A0.3845 (2)0.61156 (15)1.01271 (9)0.0175 (3)
H16A0.36800.61151.05350.021*
C17A0.4945 (2)0.69887 (15)0.99026 (9)0.0181 (3)
C18A0.5231 (3)0.69989 (16)0.92920 (9)0.0195 (4)
H18A0.59820.75920.91420.023*
C19A0.4393 (3)0.61260 (16)0.89141 (9)0.0189 (4)
H19A0.46020.61400.85090.023*
C20A0.3216 (2)0.52012 (15)0.91204 (9)0.0157 (3)
C21A−0.3028 (3)0.2735 (2)0.84529 (10)0.0243 (4)
H21A−0.31030.20430.85950.029*
C22A−0.4504 (3)0.2972 (2)0.81903 (11)0.0336 (6)
H22A−0.55470.24470.81520.040*
C23A−0.4407 (3)0.4002 (3)0.79847 (11)0.0393 (7)
H23A−0.53870.41830.78090.047*
C24A−0.2821 (4)0.4764 (2)0.80436 (11)0.0353 (6)
H24A−0.27200.54620.79080.042*
C25A−0.1397 (3)0.44592 (19)0.83093 (9)0.0237 (4)
H25A−0.03360.49670.83490.028*
Zn1B0.24994 (3)0.750502 (17)0.446624 (10)0.01377 (5)
Cl1B0.53214 (8)1.14642 (5)0.21623 (3)0.03329 (13)
Cl2B0.45724 (7)0.33521 (4)0.64416 (2)0.02195 (10)
O1B0.40173 (18)0.89342 (11)0.43171 (6)0.0168 (3)
O2B0.37564 (19)0.72741 (11)0.52269 (6)0.0189 (3)
N1B0.1634 (2)0.73368 (12)0.35419 (7)0.0142 (3)
N2B0.1587 (2)0.58051 (13)0.43293 (7)0.0142 (3)
N3B0.0454 (2)0.80835 (13)0.47794 (7)0.0160 (3)
C1B0.4220 (2)0.94502 (15)0.38263 (9)0.0152 (3)
C2B0.5361 (3)1.05123 (16)0.38571 (9)0.0192 (4)
H2BA0.59041.08040.42280.023*
C3B0.5683 (3)1.11150 (16)0.33587 (10)0.0214 (4)
H3BA0.64271.18050.33950.026*
C4B0.4892 (3)1.06911 (17)0.27962 (10)0.0222 (4)
C5B0.3774 (3)0.96788 (16)0.27388 (9)0.0198 (4)
H5BA0.32520.94070.23620.024*
C6B0.3405 (2)0.90455 (15)0.32454 (9)0.0163 (3)
C7B0.2218 (2)0.79992 (15)0.31328 (9)0.0154 (3)
H7BA0.18410.77810.27350.019*
C8B0.0507 (2)0.63124 (14)0.33783 (8)0.0135 (3)
C9B−0.0596 (2)0.60894 (15)0.28505 (8)0.0155 (3)
H9BA−0.06550.66420.25900.019*
C10B−0.1604 (2)0.50445 (16)0.27149 (9)0.0181 (3)
H10B−0.23190.48960.23600.022*
C11B−0.1547 (3)0.42217 (16)0.31074 (9)0.0187 (4)
H11B−0.22110.35200.30110.022*
C12B−0.0506 (2)0.44382 (15)0.36435 (9)0.0169 (3)
H12B−0.04980.38850.39080.020*
C13B0.0531 (2)0.54836 (15)0.37879 (8)0.0142 (3)
C14B0.1999 (2)0.50880 (15)0.46748 (8)0.0153 (3)
H14B0.15590.43610.45520.018*
C15B0.3069 (2)0.53088 (15)0.52288 (8)0.0146 (3)
C16B0.3296 (2)0.43856 (15)0.55369 (9)0.0162 (3)
H16B0.27270.36930.53830.019*
C17B0.4345 (2)0.45012 (16)0.60595 (8)0.0164 (3)
C18B0.5276 (2)0.55356 (17)0.62836 (9)0.0181 (3)
H18B0.60210.56070.66310.022*
C19B0.5087 (2)0.64438 (16)0.59897 (9)0.0179 (3)
H19B0.57290.71240.61400.021*
C20B0.3942 (2)0.63808 (15)0.54630 (8)0.0152 (3)
C21B−0.0590 (3)0.84549 (17)0.43842 (9)0.0201 (4)
H21B−0.03870.84370.39790.024*
C22B−0.1952 (3)0.88633 (18)0.45506 (11)0.0257 (4)
H22B−0.26520.91070.42610.031*
C23B−0.2268 (3)0.8907 (2)0.51480 (11)0.0291 (5)
H23B−0.31810.91760.52700.035*
C24B−0.1182 (3)0.8536 (2)0.55642 (10)0.0278 (5)
H24B−0.13540.85550.59720.033*
C25B0.0159 (3)0.81361 (17)0.53625 (9)0.0209 (4)
H25C0.08850.78940.56430.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn1A0.01486 (10)0.01347 (10)0.01347 (10)0.00164 (7)0.00036 (7)−0.00008 (7)
Cl1A0.0577 (4)0.0196 (3)0.0383 (3)0.0077 (2)0.0031 (3)−0.0118 (2)
Cl2A0.0251 (2)0.0156 (2)0.0251 (2)−0.00055 (16)−0.00211 (18)−0.00449 (17)
O1A0.0198 (6)0.0153 (6)0.0171 (6)0.0026 (5)0.0025 (5)−0.0008 (5)
O2A0.0201 (6)0.0174 (6)0.0141 (6)−0.0018 (5)0.0009 (5)−0.0014 (5)
N1A0.0170 (7)0.0156 (7)0.0165 (7)0.0018 (5)0.0007 (6)0.0003 (6)
N2A0.0157 (7)0.0138 (7)0.0150 (7)0.0024 (5)0.0010 (5)0.0014 (5)
N3A0.0174 (7)0.0215 (8)0.0156 (7)0.0064 (6)0.0015 (6)−0.0031 (6)
C1A0.0147 (8)0.0179 (8)0.0171 (8)0.0061 (6)−0.0029 (6)−0.0017 (7)
C2A0.0211 (9)0.0235 (9)0.0189 (9)0.0071 (7)0.0021 (7)−0.0024 (7)
C3A0.0272 (10)0.0257 (10)0.0234 (10)0.0110 (8)−0.0007 (8)−0.0077 (8)
C4A0.0297 (10)0.0164 (9)0.0293 (11)0.0085 (7)−0.0022 (8)−0.0074 (8)
C5A0.0259 (10)0.0152 (8)0.0247 (10)0.0047 (7)−0.0017 (8)−0.0025 (7)
C6A0.0183 (8)0.0147 (8)0.0201 (9)0.0043 (6)−0.0017 (7)−0.0002 (7)
C7A0.0190 (8)0.0142 (8)0.0191 (9)0.0025 (6)−0.0014 (7)0.0014 (7)
C8A0.0176 (8)0.0158 (8)0.0161 (8)0.0036 (6)0.0002 (6)0.0022 (6)
C9A0.0237 (9)0.0162 (8)0.0233 (10)0.0014 (7)0.0039 (7)0.0031 (7)
C10A0.0249 (10)0.0218 (9)0.0244 (10)0.0029 (7)0.0087 (8)0.0063 (8)
C11A0.0243 (9)0.0251 (10)0.0177 (9)0.0061 (7)0.0071 (7)0.0051 (7)
C12A0.0206 (9)0.0191 (9)0.0183 (9)0.0043 (7)0.0032 (7)0.0007 (7)
C13A0.0141 (7)0.0167 (8)0.0164 (8)0.0033 (6)0.0013 (6)0.0038 (6)
C14A0.0179 (8)0.0163 (8)0.0141 (8)0.0044 (6)0.0008 (6)0.0002 (6)
C15A0.0157 (8)0.0136 (8)0.0166 (8)0.0035 (6)0.0014 (6)0.0000 (6)
C16A0.0192 (8)0.0164 (8)0.0168 (8)0.0047 (6)0.0002 (7)0.0001 (7)
C17A0.0182 (8)0.0142 (8)0.0207 (9)0.0027 (6)−0.0019 (7)−0.0033 (7)
C18A0.0172 (8)0.0162 (8)0.0237 (10)0.0010 (6)0.0014 (7)0.0014 (7)
C19A0.0197 (8)0.0172 (8)0.0186 (9)0.0014 (7)0.0030 (7)0.0015 (7)
C20A0.0151 (8)0.0154 (8)0.0167 (8)0.0033 (6)0.0018 (6)0.0013 (6)
C21A0.0176 (9)0.0337 (11)0.0204 (10)0.0041 (8)0.0023 (7)−0.0041 (8)
C22A0.0175 (9)0.0593 (17)0.0241 (11)0.0113 (10)−0.0012 (8)−0.0093 (11)
C23A0.0324 (12)0.071 (2)0.0242 (11)0.0350 (13)−0.0038 (9)−0.0073 (12)
C24A0.0454 (14)0.0474 (15)0.0237 (11)0.0317 (12)0.0031 (10)0.0035 (10)
C25A0.0282 (10)0.0273 (10)0.0191 (9)0.0134 (8)0.0017 (8)0.0007 (8)
Zn1B0.01546 (10)0.01179 (10)0.01394 (10)0.00336 (7)0.00016 (7)0.00078 (7)
Cl1B0.0322 (3)0.0312 (3)0.0329 (3)−0.0022 (2)0.0057 (2)0.0176 (2)
Cl2B0.0260 (2)0.0213 (2)0.0208 (2)0.01013 (17)−0.00032 (17)0.00674 (17)
O1B0.0184 (6)0.0147 (6)0.0163 (6)0.0023 (5)0.0009 (5)0.0009 (5)
O2B0.0241 (7)0.0144 (6)0.0171 (6)0.0045 (5)−0.0044 (5)0.0004 (5)
N1B0.0142 (7)0.0117 (6)0.0170 (7)0.0038 (5)0.0012 (5)0.0014 (5)
N2B0.0155 (7)0.0135 (7)0.0133 (7)0.0031 (5)0.0011 (5)0.0004 (5)
N3B0.0160 (7)0.0133 (7)0.0188 (7)0.0029 (5)0.0031 (6)0.0008 (6)
C1B0.0150 (8)0.0135 (8)0.0181 (8)0.0045 (6)0.0030 (6)0.0009 (6)
C2B0.0185 (8)0.0152 (8)0.0229 (9)0.0019 (6)0.0029 (7)−0.0008 (7)
C3B0.0190 (9)0.0140 (8)0.0309 (11)0.0015 (6)0.0069 (8)0.0034 (7)
C4B0.0220 (9)0.0200 (9)0.0253 (10)0.0044 (7)0.0062 (7)0.0105 (8)
C5B0.0186 (8)0.0187 (9)0.0218 (9)0.0034 (7)0.0028 (7)0.0041 (7)
C6B0.0153 (8)0.0152 (8)0.0186 (9)0.0035 (6)0.0029 (6)0.0021 (7)
C7B0.0154 (8)0.0158 (8)0.0157 (8)0.0046 (6)0.0016 (6)0.0015 (6)
C8B0.0138 (7)0.0125 (7)0.0139 (8)0.0025 (6)0.0024 (6)−0.0007 (6)
C9B0.0171 (8)0.0163 (8)0.0136 (8)0.0047 (6)0.0018 (6)0.0022 (6)
C10B0.0180 (8)0.0201 (9)0.0157 (8)0.0044 (7)−0.0009 (6)−0.0005 (7)
C11B0.0189 (8)0.0158 (8)0.0197 (9)0.0013 (6)0.0012 (7)−0.0018 (7)
C12B0.0190 (8)0.0140 (8)0.0172 (8)0.0026 (6)0.0015 (6)0.0026 (6)
C13B0.0150 (7)0.0150 (8)0.0126 (8)0.0032 (6)0.0017 (6)0.0015 (6)
C14B0.0173 (8)0.0128 (7)0.0153 (8)0.0028 (6)0.0017 (6)−0.0004 (6)
C15B0.0146 (7)0.0152 (8)0.0145 (8)0.0041 (6)0.0019 (6)0.0021 (6)
C16B0.0161 (8)0.0164 (8)0.0169 (8)0.0050 (6)0.0032 (6)0.0026 (6)
C17B0.0172 (8)0.0188 (8)0.0153 (8)0.0078 (6)0.0026 (6)0.0045 (7)
C18B0.0177 (8)0.0235 (9)0.0142 (8)0.0076 (7)−0.0008 (6)0.0017 (7)
C19B0.0168 (8)0.0187 (8)0.0174 (9)0.0034 (6)0.0001 (6)−0.0012 (7)
C20B0.0158 (8)0.0156 (8)0.0143 (8)0.0040 (6)0.0020 (6)0.0009 (6)
C21B0.0206 (9)0.0209 (9)0.0201 (9)0.0079 (7)0.0015 (7)0.0013 (7)
C22B0.0197 (9)0.0245 (10)0.0341 (12)0.0088 (8)0.0008 (8)−0.0030 (9)
C23B0.0181 (9)0.0313 (11)0.0367 (12)0.0037 (8)0.0072 (8)−0.0120 (9)
C24B0.0257 (10)0.0316 (11)0.0232 (10)0.0003 (8)0.0076 (8)−0.0067 (9)
C25B0.0211 (9)0.0195 (9)0.0192 (9)−0.0013 (7)0.0030 (7)−0.0003 (7)
Geometric parameters (Å, °) top
Zn1A—O1A1.9665 (14)Zn1B—O2B1.9734 (14)
Zn1A—O2A1.9798 (13)Zn1B—O1B1.9750 (13)
Zn1A—N2A2.0815 (16)Zn1B—N3B2.0971 (17)
Zn1A—N3A2.0919 (17)Zn1B—N2B2.1076 (16)
Zn1A—N1A2.1138 (16)Zn1B—N1B2.1160 (16)
Cl1A—C4A1.748 (2)Cl1B—C4B1.750 (2)
Cl2A—C17A1.7459 (19)Cl2B—C17B1.7462 (19)
O1A—C1A1.297 (2)O1B—C1B1.291 (2)
O2A—C20A1.294 (2)O2B—C20B1.296 (2)
N1A—C7A1.293 (3)N1B—C7B1.293 (2)
N1A—C8A1.412 (3)N1B—C8B1.413 (2)
N2A—C14A1.295 (2)N2B—C14B1.293 (2)
N2A—C13A1.416 (2)N2B—C13B1.414 (2)
N3A—C25A1.343 (3)N3B—C21B1.341 (3)
N3A—C21A1.347 (3)N3B—C25B1.342 (3)
C1A—C2A1.422 (3)C1B—C2B1.430 (3)
C1A—C6A1.433 (3)C1B—C6B1.431 (3)
C2A—C3A1.377 (3)C2B—C3B1.371 (3)
C2A—H2AB0.9300C2B—H2BA0.9300
C3A—C4A1.391 (3)C3B—C4B1.396 (3)
C3A—H3AB0.9300C3B—H3BA0.9300
C4A—C5A1.370 (3)C4B—C5B1.373 (3)
C5A—C6A1.414 (3)C5B—C6B1.412 (3)
C5A—H5AB0.9300C5B—H5BA0.9300
C6A—C7A1.441 (3)C6B—C7B1.437 (3)
C7A—H7AB0.9300C7B—H7BA0.9300
C8A—C9A1.399 (3)C8B—C9B1.398 (3)
C8A—C13A1.413 (3)C8B—C13B1.413 (3)
C9A—C10A1.384 (3)C9B—C10B1.387 (3)
C9A—H9AB0.9300C9B—H9BA0.9300
C10A—C11A1.383 (3)C10B—C11B1.386 (3)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.389 (3)C11B—C12B1.388 (3)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.396 (3)C12B—C13B1.399 (3)
C12A—H12A0.9300C12B—H12B0.9300
C14A—C15A1.439 (3)C14B—C15B1.432 (3)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.412 (3)C15B—C16B1.414 (3)
C15A—C20A1.429 (3)C15B—C20B1.435 (3)
C16A—C17A1.370 (3)C16B—C17B1.369 (3)
C16A—H16A0.9300C16B—H16B0.9300
C17A—C18A1.398 (3)C17B—C18B1.402 (3)
C18A—C19A1.377 (3)C18B—C19B1.373 (3)
C18A—H18A0.9300C18B—H18B0.9300
C19A—C20A1.426 (3)C19B—C20B1.424 (3)
C19A—H19A0.9300C19B—H19B0.9300
C21A—C22A1.378 (3)C21B—C22B1.380 (3)
C21A—H21A0.9300C21B—H21B0.9300
C22A—C23A1.381 (4)C22B—C23B1.377 (3)
C22A—H22A0.9300C22B—H22B0.9300
C23A—C24A1.392 (4)C23B—C24B1.391 (4)
C23A—H23A0.9300C23B—H23B0.9300
C24A—C25A1.385 (3)C24B—C25B1.386 (3)
C24A—H24A0.9300C24B—H24B0.9300
C25A—H25A0.9300C25B—H25C0.9300
O1A—Zn1A—O2A94.27 (6)O2B—Zn1B—O1B96.46 (6)
O1A—Zn1A—N2A152.35 (6)O2B—Zn1B—N3B101.63 (6)
O2A—Zn1A—N2A90.19 (6)O1B—Zn1B—N3B97.23 (6)
O1A—Zn1A—N3A101.93 (6)O2B—Zn1B—N2B89.26 (6)
O2A—Zn1A—N3A98.92 (7)O1B—Zn1B—N2B153.84 (6)
N2A—Zn1A—N3A104.30 (6)N3B—Zn1B—N2B106.60 (6)
O1A—Zn1A—N1A88.80 (6)O2B—Zn1B—N1B159.13 (6)
O2A—Zn1A—N1A160.78 (6)O1B—Zn1B—N1B88.79 (6)
N2A—Zn1A—N1A78.67 (6)N3B—Zn1B—N1B97.70 (6)
N3A—Zn1A—N1A98.99 (7)N2B—Zn1B—N1B77.66 (6)
C1A—O1A—Zn1A130.17 (13)C1B—O1B—Zn1B130.18 (12)
C20A—O2A—Zn1A129.38 (12)C20B—O2B—Zn1B130.32 (12)
C7A—N1A—C8A121.75 (17)C7B—N1B—C8B120.31 (16)
C7A—N1A—Zn1A125.75 (14)C7B—N1B—Zn1B126.05 (13)
C8A—N1A—Zn1A112.40 (12)C8B—N1B—Zn1B112.91 (11)
C14A—N2A—C13A121.22 (16)C14B—N2B—C13B120.78 (16)
C14A—N2A—Zn1A125.28 (13)C14B—N2B—Zn1B125.35 (13)
C13A—N2A—Zn1A113.50 (12)C13B—N2B—Zn1B113.74 (12)
C25A—N3A—C21A117.93 (19)C21B—N3B—C25B117.53 (18)
C25A—N3A—Zn1A120.16 (14)C21B—N3B—Zn1B119.04 (13)
C21A—N3A—Zn1A121.81 (15)C25B—N3B—Zn1B123.39 (14)
O1A—C1A—C2A118.42 (18)O1B—C1B—C2B118.05 (17)
O1A—C1A—C6A124.65 (18)O1B—C1B—C6B125.45 (16)
C2A—C1A—C6A116.91 (18)C2B—C1B—C6B116.50 (17)
C3A—C2A—C1A122.1 (2)C3B—C2B—C1B122.30 (19)
C3A—C2A—H2AB118.9C3B—C2B—H2BA118.8
C1A—C2A—H2AB118.9C1B—C2B—H2BA118.8
C2A—C3A—C4A119.7 (2)C2B—C3B—C4B119.90 (18)
C2A—C3A—H3AB120.1C2B—C3B—H3BA120.0
C4A—C3A—H3AB120.1C4B—C3B—H3BA120.0
C5A—C4A—C3A120.89 (19)C5B—C4B—C3B120.48 (19)
C5A—C4A—Cl1A119.88 (18)C5B—C4B—Cl1B119.99 (17)
C3A—C4A—Cl1A119.21 (17)C3B—C4B—Cl1B119.53 (15)
C4A—C5A—C6A120.6 (2)C4B—C5B—C6B120.79 (19)
C4A—C5A—H5AB119.7C4B—C5B—H5BA119.6
C6A—C5A—H5AB119.7C6B—C5B—H5BA119.6
C5A—C6A—C1A119.68 (19)C5B—C6B—C1B120.01 (17)
C5A—C6A—C7A116.47 (18)C5B—C6B—C7B116.05 (17)
C1A—C6A—C7A123.82 (17)C1B—C6B—C7B123.94 (17)
N1A—C7A—C6A125.36 (18)N1B—C7B—C6B125.12 (18)
N1A—C7A—H7AB117.3N1B—C7B—H7BA117.4
C6A—C7A—H7AB117.3C6B—C7B—H7BA117.4
C9A—C8A—N1A124.64 (17)C9B—C8B—N1B124.22 (16)
C9A—C8A—C13A119.23 (18)C9B—C8B—C13B119.84 (16)
N1A—C8A—C13A116.09 (16)N1B—C8B—C13B115.94 (16)
C10A—C9A—C8A120.60 (19)C10B—C9B—C8B120.11 (17)
C10A—C9A—H9AB119.7C10B—C9B—H9BA119.9
C8A—C9A—H9AB119.7C8B—C9B—H9BA119.9
C11A—C10A—C9A120.23 (19)C11B—C10B—C9B120.19 (18)
C11A—C10A—H10A119.9C11B—C10B—H10B119.9
C9A—C10A—H10A119.9C9B—C10B—H10B119.9
C10A—C11A—C12A120.09 (19)C10B—C11B—C12B120.42 (17)
C10A—C11A—H11A120.0C10B—C11B—H11B119.8
C12A—C11A—H11A120.0C12B—C11B—H11B119.8
C11A—C12A—C13A120.62 (19)C11B—C12B—C13B120.42 (17)
C11A—C12A—H12A119.7C11B—C12B—H12B119.8
C13A—C12A—H12A119.7C13B—C12B—H12B119.8
C12A—C13A—C8A119.17 (17)C12B—C13B—C8B118.95 (16)
C12A—C13A—N2A124.60 (17)C12B—C13B—N2B125.21 (16)
C8A—C13A—N2A116.19 (17)C8B—C13B—N2B115.80 (15)
N2A—C14A—C15A125.94 (18)N2B—C14B—C15B126.11 (17)
N2A—C14A—H14A117.0N2B—C14B—H14B116.9
C15A—C14A—H14A117.0C15B—C14B—H14B116.9
C16A—C15A—C20A120.06 (17)C16B—C15B—C14B115.75 (16)
C16A—C15A—C14A115.59 (17)C16B—C15B—C20B120.06 (17)
C20A—C15A—C14A124.31 (17)C14B—C15B—C20B124.14 (17)
C17A—C16A—C15A120.92 (18)C17B—C16B—C15B120.67 (18)
C17A—C16A—H16A119.5C17B—C16B—H16B119.7
C15A—C16A—H16A119.5C15B—C16B—H16B119.7
C16A—C17A—C18A120.47 (18)C16B—C17B—C18B120.48 (17)
C16A—C17A—Cl2A120.21 (16)C16B—C17B—Cl2B119.96 (15)
C18A—C17A—Cl2A119.31 (15)C18B—C17B—Cl2B119.54 (15)
C19A—C18A—C17A119.63 (18)C19B—C18B—C17B119.85 (17)
C19A—C18A—H18A120.2C19B—C18B—H18B120.1
C17A—C18A—H18A120.2C17B—C18B—H18B120.1
C18A—C19A—C20A122.41 (18)C18B—C19B—C20B122.29 (18)
C18A—C19A—H19A118.8C18B—C19B—H19B118.9
C20A—C19A—H19A118.8C20B—C19B—H19B118.9
O2A—C20A—C19A118.70 (17)O2B—C20B—C19B119.03 (17)
O2A—C20A—C15A124.80 (16)O2B—C20B—C15B124.47 (17)
C19A—C20A—C15A116.50 (17)C19B—C20B—C15B116.49 (17)
N3A—C21A—C22A122.9 (2)N3B—C21B—C22B123.0 (2)
N3A—C21A—H21A118.6N3B—C21B—H21B118.5
C22A—C21A—H21A118.6C22B—C21B—H21B118.5
C21A—C22A—C23A118.9 (2)C23B—C22B—C21B119.5 (2)
C21A—C22A—H22A120.6C23B—C22B—H22B120.3
C23A—C22A—H22A120.6C21B—C22B—H22B120.3
C22A—C23A—C24A119.1 (2)C22B—C23B—C24B118.2 (2)
C22A—C23A—H23A120.5C22B—C23B—H23B120.9
C24A—C23A—H23A120.5C24B—C23B—H23B120.9
C25A—C24A—C23A118.5 (3)C25B—C24B—C23B119.0 (2)
C25A—C24A—H24A120.7C25B—C24B—H24B120.5
C23A—C24A—H24A120.7C23B—C24B—H24B120.5
N3A—C25A—C24A122.7 (2)N3B—C25B—C24B122.8 (2)
N3A—C25A—H25A118.6N3B—C25B—H25C118.6
C24A—C25A—H25A118.6C24B—C25B—H25C118.6
O2A—Zn1A—O1A—C1A173.52 (16)O2B—Zn1B—O1B—C1B160.82 (16)
N2A—Zn1A—O1A—C1A74.9 (2)N3B—Zn1B—O1B—C1B−96.53 (17)
N3A—Zn1A—O1A—C1A−86.41 (17)N2B—Zn1B—O1B—C1B59.2 (2)
N1A—Zn1A—O1A—C1A12.52 (17)N1B—Zn1B—O1B—C1B1.08 (17)
O1A—Zn1A—O2A—C20A−154.74 (17)O1B—Zn1B—O2B—C20B−149.62 (17)
N2A—Zn1A—O2A—C20A−2.06 (17)N3B—Zn1B—O2B—C20B111.60 (17)
N3A—Zn1A—O2A—C20A102.45 (17)N2B—Zn1B—O2B—C20B4.79 (17)
N1A—Zn1A—O2A—C20A−56.1 (3)N1B—Zn1B—O2B—C20B−45.9 (3)
O1A—Zn1A—N1A—C7A−5.56 (17)O2B—Zn1B—N1B—C7B−100.1 (2)
O2A—Zn1A—N1A—C7A−105.1 (2)O1B—Zn1B—N1B—C7B4.98 (16)
N2A—Zn1A—N1A—C7A−160.76 (18)N3B—Zn1B—N1B—C7B102.11 (16)
N3A—Zn1A—N1A—C7A96.33 (17)N2B—Zn1B—N1B—C7B−152.48 (17)
O1A—Zn1A—N1A—C8A170.79 (13)O2B—Zn1B—N1B—C8B70.0 (2)
O2A—Zn1A—N1A—C8A71.2 (2)O1B—Zn1B—N1B—C8B175.10 (13)
N2A—Zn1A—N1A—C8A15.59 (13)N3B—Zn1B—N1B—C8B−87.77 (13)
N3A—Zn1A—N1A—C8A−87.32 (13)N2B—Zn1B—N1B—C8B17.63 (12)
O1A—Zn1A—N2A—C14A100.08 (19)O2B—Zn1B—N2B—C14B−3.12 (16)
O2A—Zn1A—N2A—C14A0.49 (17)O1B—Zn1B—N2B—C14B100.12 (19)
N3A—Zn1A—N2A—C14A−98.77 (17)N3B—Zn1B—N2B—C14B−105.04 (16)
N1A—Zn1A—N2A—C14A164.72 (17)N1B—Zn1B—N2B—C14B160.49 (17)
O1A—Zn1A—N2A—C13A−79.03 (18)O2B—Zn1B—N2B—C13B−179.06 (13)
O2A—Zn1A—N2A—C13A−178.63 (13)O1B—Zn1B—N2B—C13B−75.83 (19)
N3A—Zn1A—N2A—C13A82.11 (14)N3B—Zn1B—N2B—C13B79.01 (13)
N1A—Zn1A—N2A—C13A−14.40 (13)N1B—Zn1B—N2B—C13B−15.45 (12)
O1A—Zn1A—N3A—C25A−98.16 (15)O2B—Zn1B—N3B—C21B172.35 (14)
O2A—Zn1A—N3A—C25A−1.84 (16)O1B—Zn1B—N3B—C21B74.19 (15)
N2A—Zn1A—N3A—C25A90.65 (16)N2B—Zn1B—N3B—C21B−94.92 (15)
N1A—Zn1A—N3A—C25A171.16 (15)N1B—Zn1B—N3B—C21B−15.56 (15)
O1A—Zn1A—N3A—C21A78.24 (16)O2B—Zn1B—N3B—C25B−5.46 (16)
O2A—Zn1A—N3A—C21A174.57 (15)O1B—Zn1B—N3B—C25B−103.61 (15)
N2A—Zn1A—N3A—C21A−92.94 (16)N2B—Zn1B—N3B—C25B87.28 (15)
N1A—Zn1A—N3A—C21A−12.43 (16)N1B—Zn1B—N3B—C25B166.64 (15)
Zn1A—O1A—C1A—C2A170.62 (14)Zn1B—O1B—C1B—C2B176.85 (13)
Zn1A—O1A—C1A—C6A−10.9 (3)Zn1B—O1B—C1B—C6B−3.7 (3)
O1A—C1A—C2A—C3A−179.22 (19)O1B—C1B—C2B—C3B178.84 (19)
C6A—C1A—C2A—C3A2.2 (3)C6B—C1B—C2B—C3B−0.7 (3)
C1A—C2A—C3A—C4A−1.1 (3)C1B—C2B—C3B—C4B−0.4 (3)
C2A—C3A—C4A—C5A−0.7 (3)C2B—C3B—C4B—C5B0.9 (3)
C2A—C3A—C4A—Cl1A−179.45 (17)C2B—C3B—C4B—Cl1B−179.64 (17)
C3A—C4A—C5A—C6A1.3 (3)C3B—C4B—C5B—C6B−0.2 (3)
Cl1A—C4A—C5A—C6A−179.88 (16)Cl1B—C4B—C5B—C6B−179.70 (16)
C4A—C5A—C6A—C1A−0.2 (3)C4B—C5B—C6B—C1B−0.9 (3)
C4A—C5A—C6A—C7A−178.3 (2)C4B—C5B—C6B—C7B−179.95 (19)
O1A—C1A—C6A—C5A−179.97 (19)O1B—C1B—C6B—C5B−178.17 (19)
C2A—C1A—C6A—C5A−1.5 (3)C2B—C1B—C6B—C5B1.3 (3)
O1A—C1A—C6A—C7A−2.1 (3)O1B—C1B—C6B—C7B0.8 (3)
C2A—C1A—C6A—C7A176.47 (19)C2B—C1B—C6B—C7B−179.71 (18)
C8A—N1A—C7A—C6A−179.00 (18)C8B—N1B—C7B—C6B−178.18 (18)
Zn1A—N1A—C7A—C6A−3.0 (3)Zn1B—N1B—C7B—C6B−8.7 (3)
C5A—C6A—C7A—N1A−173.03 (19)C5B—C6B—C7B—N1B−175.09 (19)
C1A—C6A—C7A—N1A9.0 (3)C1B—C6B—C7B—N1B5.9 (3)
C7A—N1A—C8A—C9A−20.4 (3)C7B—N1B—C8B—C9B−27.0 (3)
Zn1A—N1A—C8A—C9A163.06 (17)Zn1B—N1B—C8B—C9B162.22 (15)
C7A—N1A—C8A—C13A161.92 (18)C7B—N1B—C8B—C13B153.22 (18)
Zn1A—N1A—C8A—C13A−14.6 (2)Zn1B—N1B—C8B—C13B−17.5 (2)
N1A—C8A—C9A—C10A180.0 (2)N1B—C8B—C9B—C10B177.18 (18)
C13A—C8A—C9A—C10A−2.4 (3)C13B—C8B—C9B—C10B−3.1 (3)
C8A—C9A—C10A—C11A0.4 (3)C8B—C9B—C10B—C11B1.2 (3)
C9A—C10A—C11A—C12A1.8 (3)C9B—C10B—C11B—C12B1.1 (3)
C10A—C11A—C12A—C13A−1.9 (3)C10B—C11B—C12B—C13B−1.5 (3)
C11A—C12A—C13A—C8A−0.2 (3)C11B—C12B—C13B—C8B−0.3 (3)
C11A—C12A—C13A—N2A177.24 (19)C11B—C12B—C13B—N2B177.46 (18)
C9A—C8A—C13A—C12A2.3 (3)C9B—C8B—C13B—C12B2.6 (3)
N1A—C8A—C13A—C12A−179.89 (18)N1B—C8B—C13B—C12B−177.65 (17)
C9A—C8A—C13A—N2A−175.29 (18)C9B—C8B—C13B—N2B−175.37 (17)
N1A—C8A—C13A—N2A2.5 (3)N1B—C8B—C13B—N2B4.4 (2)
C14A—N2A—C13A—C12A14.5 (3)C14B—N2B—C13B—C12B17.1 (3)
Zn1A—N2A—C13A—C12A−166.32 (16)Zn1B—N2B—C13B—C12B−166.78 (16)
C14A—N2A—C13A—C8A−168.00 (18)C14B—N2B—C13B—C8B−165.12 (17)
Zn1A—N2A—C13A—C8A11.1 (2)Zn1B—N2B—C13B—C8B11.0 (2)
C13A—N2A—C14A—C15A−178.79 (18)C13B—N2B—C14B—C15B179.31 (17)
Zn1A—N2A—C14A—C15A2.2 (3)Zn1B—N2B—C14B—C15B3.6 (3)
N2A—C14A—C15A—C16A178.22 (19)N2B—C14B—C15B—C16B178.27 (18)
N2A—C14A—C15A—C20A−4.0 (3)N2B—C14B—C15B—C20B−4.3 (3)
C20A—C15A—C16A—C17A0.7 (3)C14B—C15B—C16B—C17B177.56 (17)
C14A—C15A—C16A—C17A178.59 (18)C20B—C15B—C16B—C17B0.0 (3)
C15A—C16A—C17A—C18A−0.9 (3)C15B—C16B—C17B—C18B−3.0 (3)
C15A—C16A—C17A—Cl2A−179.71 (15)C15B—C16B—C17B—Cl2B178.64 (14)
C16A—C17A—C18A—C19A0.3 (3)C16B—C17B—C18B—C19B2.4 (3)
Cl2A—C17A—C18A—C19A179.07 (16)Cl2B—C17B—C18B—C19B−179.17 (15)
C17A—C18A—C19A—C20A0.6 (3)C17B—C18B—C19B—C20B1.1 (3)
Zn1A—O2A—C20A—C19A−179.07 (14)Zn1B—O2B—C20B—C19B172.92 (13)
Zn1A—O2A—C20A—C15A1.0 (3)Zn1B—O2B—C20B—C15B−6.8 (3)
C18A—C19A—C20A—O2A179.36 (19)C18B—C19B—C20B—O2B176.31 (18)
C18A—C19A—C20A—C15A−0.7 (3)C18B—C19B—C20B—C15B−3.9 (3)
C16A—C15A—C20A—O2A179.99 (19)C16B—C15B—C20B—O2B−176.93 (18)
C14A—C15A—C20A—O2A2.3 (3)C14B—C15B—C20B—O2B5.7 (3)
C16A—C15A—C20A—C19A0.1 (3)C16B—C15B—C20B—C19B3.3 (3)
C14A—C15A—C20A—C19A−177.60 (18)C14B—C15B—C20B—C19B−174.00 (17)
C25A—N3A—C21A—C22A0.6 (3)C25B—N3B—C21B—C22B−1.2 (3)
Zn1A—N3A—C21A—C22A−175.93 (17)Zn1B—N3B—C21B—C22B−179.15 (16)
N3A—C21A—C22A—C23A−0.8 (3)N3B—C21B—C22B—C23B0.5 (3)
C21A—C22A—C23A—C24A0.6 (4)C21B—C22B—C23B—C24B0.2 (3)
C22A—C23A—C24A—C25A−0.2 (4)C22B—C23B—C24B—C25B−0.3 (3)
C21A—N3A—C25A—C24A−0.1 (3)C21B—N3B—C25B—C24B1.2 (3)
Zn1A—N3A—C25A—C24A176.41 (17)Zn1B—N3B—C25B—C24B178.99 (15)
C23A—C24A—C25A—N3A0.0 (4)C23B—C24B—C25B—N3B−0.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C9B—H9BA···O1Ai0.932.353.261 (2)167
C21B—H21B···N1B0.932.593.198 (3)123
C22A—H22A···O1Aii0.932.423.199 (3)141
C25A—H25A···O2A0.932.603.175 (3)121
C5B—H5BA···Cg3i0.933.063.463 (3)108
C21A—H21A···Cg10.932.973.397 (3)109
C21B—H21B···Cg20.932.803.301 (2)115
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C9B—H9BA···O1Ai0.932.353.261 (2)167
C21B—H21B···N1B0.932.593.198 (3)123
C22A—H22A···O1Aii0.932.423.199 (3)141
C25A—H25A···O2A0.932.603.175 (3)121
C5B—H5BA···Cg3i0.933.063.463 (3)108
C21A—H21A···Cg10.932.973.397 (3)109
C21B—H21B···Cg20.932.803.301 (2)115
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z.
Acknowledgements top

The authors thank the Malaysian Government, the Ministry of Science Technology and Innovation, Malaysia (MOSTI), and Universiti Sains Malaysia for research grants 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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