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Acta Cryst. (2008). E64, m421    [ doi:10.1107/S1600536808002213 ]

Bis{4-chloro-2-[2-(1H-indol-3-yl)ethyliminomethyl]phenolato-[kappa]2N,O}zinc(II)

H. M. Ali, M. I. Mohamed Mustafa, M. R. Rizal and S. W. Ng

Abstract top

The Zn atom in the title compound, [Zn(C17H14ClN2O)2], is N,O-chelated by two deprotonated Schiff base monoanionic ligands in a tetrahedral coordination geometry. The Zn atom lies on a special position of site symmetry 2.

Comment top

We have recently reported the low-temperature structure of the zinc derivative of the ligand without any substituent, [C17H15N2O)2Zn] (Ng, 2008); the low-temperature structure is identical to the room-temperature structure (Chen et al., 2007). The present compound has a chlorine substituent but this does not lead to significant changes to the bond dimensions of the central metal.

Related literature top

For the structure of the unsubstituted [(C17H15N2O)2Zn], see Chen et al. (2007); Ng (2008).

Experimental top

The Schiff base ligand was synthesized by the reaction of tryptamine (0.32 g, 2 mmol), 5-chlorosalicylaldehyde (0.24 g, 2 mmol) and zinc acetate (0.19 g, 1 mmol) in ethanol. There organic reagents were first heated for an hour. Zinc acetate was then added followed by excess of triethylamine (1 ml). Crystals were obtained by recrystallization from dimethylformamide.

Refinement top

All H atoms were located in a difference Fourier map, and were refined with distance restraints of C–H 1.00 Å and N–H 0.88 Å; their temperature factors were freely refined.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of Zn(C17H14ClN2O). Displacement ellipsoids are drawn at the 50% probability level, and H atoms are shown as spheres of arbitrary radii.
Bis{4-chloro-2-[2-(1H-indol-3-yl)ethyliminomethyl]phenolato- κ2N,O}zinc(II) top
Crystal data top
[Zn(C17H14ClN2O)2]F(000) = 1360
Mr = 660.87Dx = 1.497 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9956 reflections
a = 25.8989 (3) Åθ = 2.5–31.2°
b = 5.4960 (1) ŵ = 1.06 mm−1
c = 20.6138 (3) ÅT = 128 K
β = 91.801 (1)°Block, colorless
V = 2932.73 (8) Å30.50 × 0.30 × 0.17 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer		3352 independent reflections
Radiation source: medium-focus sealed tube3023 reflections with I > 2σ(I)
graphiteRint = 0.025
φ and ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −33→33
Tmin = 0.714, Tmax = 0.840k = −6→7
17664 measured reflectionsl = −26→26
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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100All H-atom parameters refined
S = 1.21 w = 1/[σ2(Fo2) + (0.0632P)2 + 1.1156P]
where P = (Fo2 + 2Fc2)/3
3352 reflections(Δ/σ)max = 0.001
251 parametersΔρmax = 0.55 e Å−3
14 restraintsΔρmin = −0.56 e Å−3
Crystal data top
[Zn(C17H14ClN2O)2]V = 2932.73 (8) Å3
Mr = 660.87Z = 4
Monoclinic, C2/cMo Kα radiation
a = 25.8989 (3) ŵ = 1.06 mm−1
b = 5.4960 (1) ÅT = 128 K
c = 20.6138 (3) Å0.50 × 0.30 × 0.17 mm
β = 91.801 (1)°
Data collection top
Bruker APEXII
diffractometer		3023 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.025
Tmin = 0.714, Tmax = 0.840θmax = 27.5°
17664 measured reflectionsStandard reflections: 0
3352 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.025All H-atom parameters refined
wR(F2) = 0.100Δρmax = 0.55 e Å−3
S = 1.21Δρmin = −0.56 e Å−3
3352 reflectionsAbsolute structure: ?
251 parametersFlack parameter: ?
14 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.50000.49480 (5)0.75000.01823 (11)
Cl10.39490 (2)0.33657 (10)0.42675 (2)0.03469 (14)
O10.46240 (5)0.6771 (2)0.68555 (6)0.0256 (3)
N10.53085 (5)0.2579 (3)0.68736 (6)0.0167 (3)
C10.45075 (6)0.5975 (3)0.62688 (7)0.0175 (3)
N20.71557 (6)−0.2875 (3)0.76815 (7)0.0235 (3)
C20.41428 (7)0.7308 (3)0.58836 (8)0.0226 (3)
C30.39787 (7)0.6548 (3)0.52766 (8)0.0230 (3)
C40.41765 (7)0.4409 (4)0.50234 (8)0.0216 (3)
C50.45433 (7)0.3096 (3)0.53648 (8)0.0206 (3)
C60.47188 (6)0.3836 (3)0.59882 (7)0.0167 (3)
C70.51092 (6)0.2301 (3)0.63013 (8)0.0181 (3)
C80.56967 (6)0.0809 (3)0.71064 (8)0.0186 (3)
C90.62386 (7)0.1885 (4)0.70984 (11)0.0305 (4)
C100.66211 (7)0.0247 (3)0.74448 (10)0.0233 (4)
C110.68435 (7)−0.1805 (3)0.72056 (9)0.0245 (4)
C120.68028 (6)0.0477 (3)0.81090 (9)0.0209 (3)
C130.67219 (7)0.2182 (4)0.86012 (10)0.0296 (4)
C150.69689 (9)0.1852 (4)0.91969 (10)0.0359 (5)
C160.72995 (9)−0.0135 (4)0.93160 (11)0.0344 (5)
C170.73904 (7)−0.1845 (4)0.88415 (9)0.0279 (4)
C180.71359 (6)−0.1517 (3)0.82397 (8)0.0205 (3)
H2N0.7331 (9)−0.421 (3)0.7639 (13)0.042 (7)*
H20.3996 (9)0.884 (3)0.6056 (11)0.036 (6)*
H30.3712 (7)0.753 (4)0.5031 (10)0.033 (6)*
H50.4670 (8)0.155 (3)0.5170 (11)0.036 (6)*
H70.5240 (7)0.097 (3)0.6024 (8)0.017 (5)*
H810.5617 (8)0.033 (3)0.7554 (6)0.018 (5)*
H820.5676 (9)−0.067 (3)0.6831 (10)0.028 (5)*
H910.6237 (11)0.351 (3)0.7316 (12)0.052 (8)*
H920.6344 (10)0.217 (5)0.6640 (6)0.048 (8)*
H110.6818 (9)−0.251 (4)0.6764 (6)0.034 (6)*
H130.6501 (8)0.365 (3)0.8521 (11)0.038 (6)*
H150.6893 (9)0.299 (4)0.9553 (9)0.037 (6)*
H160.7477 (10)−0.026 (5)0.9748 (8)0.045 (8)*
H170.7634 (8)−0.323 (3)0.8917 (12)0.041 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02395 (17)0.01667 (17)0.01391 (15)0.000−0.00209 (10)0.000
Cl10.0418 (3)0.0423 (3)0.0191 (2)0.0051 (2)−0.01249 (18)−0.00457 (18)
O10.0394 (7)0.0195 (6)0.0173 (6)0.0091 (5)−0.0061 (5)−0.0035 (5)
N10.0163 (6)0.0165 (7)0.0174 (6)0.0011 (5)−0.0005 (5)0.0026 (5)
C10.0215 (7)0.0158 (8)0.0153 (7)0.0005 (6)−0.0003 (6)0.0006 (6)
N20.0211 (7)0.0231 (8)0.0262 (7)0.0056 (6)−0.0016 (6)−0.0016 (6)
C20.0264 (9)0.0193 (8)0.0222 (8)0.0065 (7)0.0000 (6)0.0018 (6)
C30.0227 (8)0.0247 (9)0.0212 (8)0.0039 (7)−0.0029 (6)0.0072 (7)
C40.0236 (8)0.0268 (8)0.0142 (7)−0.0009 (7)−0.0026 (6)−0.0005 (6)
C50.0231 (8)0.0214 (8)0.0172 (7)0.0029 (6)−0.0001 (6)−0.0021 (6)
C60.0185 (7)0.0168 (8)0.0148 (7)0.0013 (6)−0.0005 (5)0.0007 (6)
C70.0186 (7)0.0173 (8)0.0186 (7)0.0030 (6)0.0006 (6)−0.0001 (6)
C80.0183 (7)0.0173 (8)0.0201 (7)0.0020 (6)−0.0025 (6)0.0032 (6)
C90.0186 (8)0.0281 (10)0.0444 (11)−0.0022 (7)−0.0044 (7)0.0164 (9)
C100.0154 (7)0.0226 (9)0.0319 (10)−0.0029 (6)−0.0015 (7)0.0075 (7)
C110.0206 (8)0.0281 (9)0.0246 (8)−0.0026 (7)−0.0040 (6)0.0022 (7)
C120.0152 (7)0.0179 (8)0.0298 (9)−0.0013 (6)0.0030 (6)0.0036 (7)
C130.0264 (9)0.0199 (9)0.0431 (11)−0.0029 (7)0.0094 (8)−0.0036 (8)
C150.0408 (11)0.0315 (11)0.0359 (10)−0.0118 (9)0.0098 (8)−0.0126 (9)
C160.0399 (11)0.0382 (12)0.0249 (10)−0.0122 (8)−0.0022 (8)0.0001 (8)
C170.0265 (9)0.0293 (10)0.0275 (9)−0.0020 (7)−0.0043 (7)0.0047 (7)
C180.0179 (7)0.0194 (8)0.0241 (8)−0.0010 (6)0.0010 (6)0.0018 (6)
Geometric parameters (Å, °) top
Zn1—O11.907 (1)C7—H70.994 (9)
Zn1—O1i1.907 (1)C8—C91.523 (2)
Zn1—N12.016 (1)C8—H810.989 (9)
Zn1—N1i2.016 (1)C8—H820.994 (10)
Cl1—C41.745 (2)C9—C101.502 (2)
O1—C11.312 (2)C9—H910.998 (10)
N1—C71.282 (2)C9—H921.004 (10)
N1—C81.469 (2)C10—C111.366 (3)
C1—C21.419 (2)C10—C121.439 (3)
C1—C61.427 (2)C11—H110.990 (10)
N2—C181.374 (2)C12—C131.402 (3)
N2—C111.383 (2)C12—C181.415 (2)
N2—H2N0.870 (10)C13—C151.379 (3)
C2—C31.374 (2)C13—H130.998 (10)
C2—H20.994 (10)C15—C161.405 (3)
C3—C41.391 (3)C15—H150.990 (10)
C3—H31.001 (10)C16—C171.382 (3)
C4—C51.370 (2)C16—H160.992 (10)
C5—C61.410 (2)C17—C181.398 (2)
C5—H50.999 (10)C17—H170.996 (10)
C6—C71.453 (2)
O1—Zn1—O1i116.62 (8)N1—C8—H81108.7 (12)
O1—Zn1—N195.57 (5)C9—C8—H81109.5 (12)
O1—Zn1—N1i125.55 (6)N1—C8—H82109.4 (14)
O1i—Zn1—N1125.55 (6)C9—C8—H82110.3 (13)
O1i—Zn1—N1i95.57 (5)H81—C8—H82107.8 (18)
N1—Zn1—N1i99.56 (8)C10—C9—C8110.87 (15)
C1—O1—Zn1124.38 (11)C10—C9—H91109.5 (17)
C7—N1—C8118.25 (14)C8—C9—H91109.0 (16)
C7—N1—Zn1120.68 (11)C10—C9—H92110.3 (16)
C8—N1—Zn1119.96 (10)C8—C9—H92110.3 (15)
O1—C1—C2118.25 (15)H91—C9—H92107 (2)
O1—C1—C6124.63 (15)C11—C10—C12106.68 (16)
C2—C1—C6117.12 (14)C11—C10—C9127.04 (19)
C18—N2—C11109.06 (15)C12—C10—C9126.20 (17)
C18—N2—H2N125.3 (18)C10—C11—N2109.81 (16)
C11—N2—H2N125.7 (18)C10—C11—H11129.7 (14)
C3—C2—C1122.28 (16)N2—C11—H11120.4 (14)
C3—C2—H2118.2 (14)C13—C12—C18118.94 (17)
C1—C2—H2119.6 (14)C13—C12—C10134.06 (17)
C2—C3—C4119.47 (15)C18—C12—C10106.99 (15)
C2—C3—H3119.0 (14)C15—C13—C12118.76 (19)
C4—C3—H3121.5 (14)C15—C13—H13120.0 (14)
C5—C4—C3120.68 (16)C12—C13—H13121.2 (14)
C5—C4—Cl1119.65 (14)C13—C15—C16121.40 (19)
C3—C4—Cl1119.66 (13)C13—C15—H15118.7 (15)
C4—C5—C6120.98 (16)C16—C15—H15119.8 (15)
C4—C5—H5118.2 (14)C17—C16—C15121.4 (2)
C6—C5—H5120.8 (14)C17—C16—H16120.4 (16)
C5—C6—C1119.38 (14)C15—C16—H16118.2 (16)
C5—C6—C7115.93 (14)C16—C17—C18117.02 (18)
C1—C6—C7124.69 (14)C16—C17—H17121.9 (15)
N1—C7—C6126.44 (15)C18—C17—H17121.1 (15)
N1—C7—H7118.8 (12)N2—C18—C17130.10 (17)
C6—C7—H7114.6 (12)N2—C18—C12107.45 (15)
N1—C8—C9111.15 (14)C17—C18—C12122.43 (17)
O1i—Zn1—O1—C1153.77 (15)C1—C6—C7—N12.3 (3)
N1—Zn1—O1—C119.16 (14)C7—N1—C8—C9104.80 (18)
N1i—Zn1—O1—C1−86.78 (15)Zn1—N1—C8—C9−87.15 (16)
O1—Zn1—N1—C7−18.84 (14)N1—C8—C9—C10169.91 (16)
O1i—Zn1—N1—C7−147.38 (12)C8—C9—C10—C1179.8 (2)
N1i—Zn1—N1—C7108.67 (14)C8—C9—C10—C12−96.6 (2)
O1—Zn1—N1—C8173.41 (12)C12—C10—C11—N2−0.1 (2)
O1i—Zn1—N1—C844.87 (14)C9—C10—C11—N2−177.12 (16)
N1i—Zn1—N1—C8−59.09 (10)C18—N2—C11—C100.3 (2)
Zn1—O1—C1—C2167.80 (12)C11—C10—C12—C13178.99 (19)
Zn1—O1—C1—C6−11.6 (2)C9—C10—C12—C13−4.0 (3)
O1—C1—C2—C3−176.76 (17)C11—C10—C12—C18−0.05 (19)
C6—C1—C2—C32.7 (3)C9—C10—C12—C18176.96 (16)
C1—C2—C3—C4−0.4 (3)C18—C12—C13—C15−0.2 (3)
C2—C3—C4—C5−1.9 (3)C10—C12—C13—C15−179.14 (19)
C2—C3—C4—Cl1177.25 (14)C12—C13—C15—C160.4 (3)
C3—C4—C5—C61.8 (3)C13—C15—C16—C17−0.1 (3)
Cl1—C4—C5—C6−177.31 (13)C15—C16—C17—C18−0.4 (3)
C4—C5—C6—C10.5 (3)C11—N2—C18—C17−178.80 (18)
C4—C5—C6—C7−179.84 (16)C11—N2—C18—C12−0.31 (19)
O1—C1—C6—C5176.72 (16)C16—C17—C18—N2178.95 (18)
C2—C1—C6—C5−2.7 (2)C16—C17—C18—C120.7 (3)
O1—C1—C6—C7−2.9 (3)C13—C12—C18—N2−178.99 (16)
C2—C1—C6—C7177.69 (15)C10—C12—C18—N20.22 (19)
C8—N1—C7—C6179.43 (15)C13—C12—C18—C17−0.4 (3)
Zn1—N1—C7—C611.5 (2)C10—C12—C18—C17178.85 (16)
C5—C6—C7—N1−177.31 (16)
Symmetry codes: (i) −x+1, y, −z+3/2.
Table 1
Selected geometric parameters (Å, °) top
Zn1—O11.907 (1)Zn1—N12.016 (1)
O1—Zn1—O1i116.62 (8)O1—Zn1—N1i125.55 (6)
O1—Zn1—N195.57 (5)N1—Zn1—N1i99.56 (8)
Symmetry codes: (i) −x+1, y, −z+3/2.
Acknowledgements top

The authors thank the University of Canterbury, New Zealand, for the diffraction measurements, and the Science Fund (12–02–03–2031) for supporting this study.

references
References top

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Westrip, S. P. (2008). publCIF. In preparation.