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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m421.
Published online 2008 January 25. doi: 10.1107/S1600536808002213.
PMCID: PMC2960352
Bis{4-chloro-2-[2-(1H-indol-3-yl)ethyl­imino­meth­yl]phenolato-κ2 N,O}zinc(II)
Hapipah M. Ali,a M. I Mohamed Mustafa,a Mohd. Razali Rizal,a and Seik Weng Nga*
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng/at/um.edu.my
Received January 7, 2008; Accepted January 21, 2008.
Abstract
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.
Related literature
For the structure of the unsubstituted [(C17H15N2O)2Zn], see Chen et al. (2007 [triangle]); Ng (2008 [triangle]).
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Object name is e-64-0m421-scheme1.jpg Object name is e-64-0m421-scheme1.jpg
Crystal data
  • [Zn(C17H14ClN2O)2]
  • M r = 660.87
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m421-efi1.jpg
  • a = 25.8989 (3) Å
  • b = 5.4960 (1) Å
  • c = 20.6138 (3) Å
  • β = 91.801 (1)°
  • V = 2932.73 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.06 mm−1
  • T = 128 (2) K
  • 0.50 × 0.30 × 0.17 mm
Data collection
  • Bruker APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.714, T max = 0.840
  • 17664 measured reflections
  • 3352 independent reflections
  • 3023 reflections with I > 2σ(I)
  • R int = 0.025
Refinement
  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.100
  • S = 1.21
  • 3352 reflections
  • 251 parameters
  • 14 restraints
  • All H-atom parameters refined
  • Δρmax = 0.55 e Å−3
  • Δρmin = −0.56 e Å−3
Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).
Table 1
Table 1
Selected geometric parameters (Å, °)
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002213/hg2370sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002213/hg2370Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
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.
supplementary crystallographic information
Comment
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.
Experimental
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
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.
Figures
Fig. 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.
Crystal data
[Zn(C17H14ClN2O)2]F(000) = 1360
Mr = 660.87Dx = 1.497 Mg m3
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 mm1
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
Bruker APEXII diffractometer3352 independent reflections
Radiation source: medium-focus sealed tube3023 reflections with I > 2σ(I)
graphiteRint = 0.025
[var phi] 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
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 = 1.21w = 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 Å3
14 restraintsΔρmin = −0.56 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
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)
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, °)
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.
 
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2370).
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