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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m421. | 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 Received January 7, 2008; Accepted January 21, 2008. This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. 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. For the structure of the unsubstituted [(C 17H 15N 2O) 2Zn], see Chen et al. (2007 ![[triangle]](/corehtml/pmc/pmcents/rtrif.gif) ); Ng (2008 ). Click on image to enlarge  Crystal data
- [Zn(C17H14ClN2O)2]
-
M
r = 660.87
- Monoclinic,
-
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 ) 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 ); cell refinement: SAINT (Bruker, 2005 ); data reduction: SAINT; 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 ).
| Table 1Selected geometric parameters (Å, °) |
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
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. Crystal data | [Zn(C17H14ClN2O)2] | F(000) = 1360 | | Mr = 660.87 | Dx = 1.497 Mg m−3 | | Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å | | Hall symbol: -C 2yc | Cell parameters from 9956 reflections | | a = 25.8989 (3) Å | θ = 2.5–31.2° | | b = 5.4960 (1) Å | µ = 1.06 mm−1 | | c = 20.6138 (3) Å | T = 128 K | | β = 91.801 (1)° | Block, colorless | | V = 2932.73 (8) Å3 | 0.50 × 0.30 × 0.17 mm | | Z = 4 | |
Data collection | Bruker APEXII diffractometer | 3352 independent reflections | | Radiation source: medium-focus sealed tube | 3023 reflections with I > 2σ(I) | | graphite | Rint = 0.025 | ![[var phi]](/corehtml/pmc/pmcents/x03C6.gif) and ω scans | θmax = 27.5°, θmin = 1.6° | | Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −33→33 | | Tmin = 0.714, Tmax = 0.840 | k = −6→7 | | 17664 measured reflections | l = −26→26 |
Refinement | Refinement on F2 | Primary atom site location: structure-invariant direct methods | | Least-squares matrix: full | Secondary atom site location: difference Fourier map | | R[F2 > 2σ(F2)] = 0.025 | Hydrogen site location: inferred from neighbouring sites | | wR(F2) = 0.100 | All 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 parameters | Δρmax = 0.55 e Å−3 | | 14 restraints | Δρmin = −0.56 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) | x | y | z | Uiso*/Ueq | | | Zn1 | 0.5000 | 0.49480 (5) | 0.7500 | 0.01823 (11) | | | Cl1 | 0.39490 (2) | 0.33657 (10) | 0.42675 (2) | 0.03469 (14) | | | O1 | 0.46240 (5) | 0.6771 (2) | 0.68555 (6) | 0.0256 (3) | | | N1 | 0.53085 (5) | 0.2579 (3) | 0.68736 (6) | 0.0167 (3) | | | C1 | 0.45075 (6) | 0.5975 (3) | 0.62688 (7) | 0.0175 (3) | | | N2 | 0.71557 (6) | −0.2875 (3) | 0.76815 (7) | 0.0235 (3) | | | C2 | 0.41428 (7) | 0.7308 (3) | 0.58836 (8) | 0.0226 (3) | | | C3 | 0.39787 (7) | 0.6548 (3) | 0.52766 (8) | 0.0230 (3) | | | C4 | 0.41765 (7) | 0.4409 (4) | 0.50234 (8) | 0.0216 (3) | | | C5 | 0.45433 (7) | 0.3096 (3) | 0.53648 (8) | 0.0206 (3) | | | C6 | 0.47188 (6) | 0.3836 (3) | 0.59882 (7) | 0.0167 (3) | | | C7 | 0.51092 (6) | 0.2301 (3) | 0.63013 (8) | 0.0181 (3) | | | C8 | 0.56967 (6) | 0.0809 (3) | 0.71064 (8) | 0.0186 (3) | | | C9 | 0.62386 (7) | 0.1885 (4) | 0.70984 (11) | 0.0305 (4) | | | C10 | 0.66211 (7) | 0.0247 (3) | 0.74448 (10) | 0.0233 (4) | | | C11 | 0.68435 (7) | −0.1805 (3) | 0.72056 (9) | 0.0245 (4) | | | C12 | 0.68028 (6) | 0.0477 (3) | 0.81090 (9) | 0.0209 (3) | | | C13 | 0.67219 (7) | 0.2182 (4) | 0.86012 (10) | 0.0296 (4) | | | C15 | 0.69689 (9) | 0.1852 (4) | 0.91969 (10) | 0.0359 (5) | | | C16 | 0.72995 (9) | −0.0135 (4) | 0.93160 (11) | 0.0344 (5) | | | C17 | 0.73904 (7) | −0.1845 (4) | 0.88415 (9) | 0.0279 (4) | | | C18 | 0.71359 (6) | −0.1517 (3) | 0.82397 (8) | 0.0205 (3) | | | H2N | 0.7331 (9) | −0.421 (3) | 0.7639 (13) | 0.042 (7)* | | | H2 | 0.3996 (9) | 0.884 (3) | 0.6056 (11) | 0.036 (6)* | | | H3 | 0.3712 (7) | 0.753 (4) | 0.5031 (10) | 0.033 (6)* | | | H5 | 0.4670 (8) | 0.155 (3) | 0.5170 (11) | 0.036 (6)* | | | H7 | 0.5240 (7) | 0.097 (3) | 0.6024 (8) | 0.017 (5)* | | | H81 | 0.5617 (8) | 0.033 (3) | 0.7554 (6) | 0.018 (5)* | | | H82 | 0.5676 (9) | −0.067 (3) | 0.6831 (10) | 0.028 (5)* | | | H91 | 0.6237 (11) | 0.351 (3) | 0.7316 (12) | 0.052 (8)* | | | H92 | 0.6344 (10) | 0.217 (5) | 0.6640 (6) | 0.048 (8)* | | | H11 | 0.6818 (9) | −0.251 (4) | 0.6764 (6) | 0.034 (6)* | | | H13 | 0.6501 (8) | 0.365 (3) | 0.8521 (11) | 0.038 (6)* | | | H15 | 0.6893 (9) | 0.299 (4) | 0.9553 (9) | 0.037 (6)* | | | H16 | 0.7477 (10) | −0.026 (5) | 0.9748 (8) | 0.045 (8)* | | | H17 | 0.7634 (8) | −0.323 (3) | 0.8917 (12) | 0.041 (7)* | |
Atomic displacement parameters (Å2) | U11 | U22 | U33 | U12 | U13 | U23 | | Zn1 | 0.02395 (17) | 0.01667 (17) | 0.01391 (15) | 0.000 | −0.00209 (10) | 0.000 | | Cl1 | 0.0418 (3) | 0.0423 (3) | 0.0191 (2) | 0.0051 (2) | −0.01249 (18) | −0.00457 (18) | | O1 | 0.0394 (7) | 0.0195 (6) | 0.0173 (6) | 0.0091 (5) | −0.0061 (5) | −0.0035 (5) | | N1 | 0.0163 (6) | 0.0165 (7) | 0.0174 (6) | 0.0011 (5) | −0.0005 (5) | 0.0026 (5) | | C1 | 0.0215 (7) | 0.0158 (8) | 0.0153 (7) | 0.0005 (6) | −0.0003 (6) | 0.0006 (6) | | N2 | 0.0211 (7) | 0.0231 (8) | 0.0262 (7) | 0.0056 (6) | −0.0016 (6) | −0.0016 (6) | | C2 | 0.0264 (9) | 0.0193 (8) | 0.0222 (8) | 0.0065 (7) | 0.0000 (6) | 0.0018 (6) | | C3 | 0.0227 (8) | 0.0247 (9) | 0.0212 (8) | 0.0039 (7) | −0.0029 (6) | 0.0072 (7) | | C4 | 0.0236 (8) | 0.0268 (8) | 0.0142 (7) | −0.0009 (7) | −0.0026 (6) | −0.0005 (6) | | C5 | 0.0231 (8) | 0.0214 (8) | 0.0172 (7) | 0.0029 (6) | −0.0001 (6) | −0.0021 (6) | | C6 | 0.0185 (7) | 0.0168 (8) | 0.0148 (7) | 0.0013 (6) | −0.0005 (5) | 0.0007 (6) | | C7 | 0.0186 (7) | 0.0173 (8) | 0.0186 (7) | 0.0030 (6) | 0.0006 (6) | −0.0001 (6) | | C8 | 0.0183 (7) | 0.0173 (8) | 0.0201 (7) | 0.0020 (6) | −0.0025 (6) | 0.0032 (6) | | C9 | 0.0186 (8) | 0.0281 (10) | 0.0444 (11) | −0.0022 (7) | −0.0044 (7) | 0.0164 (9) | | C10 | 0.0154 (7) | 0.0226 (9) | 0.0319 (10) | −0.0029 (6) | −0.0015 (7) | 0.0075 (7) | | C11 | 0.0206 (8) | 0.0281 (9) | 0.0246 (8) | −0.0026 (7) | −0.0040 (6) | 0.0022 (7) | | C12 | 0.0152 (7) | 0.0179 (8) | 0.0298 (9) | −0.0013 (6) | 0.0030 (6) | 0.0036 (7) | | C13 | 0.0264 (9) | 0.0199 (9) | 0.0431 (11) | −0.0029 (7) | 0.0094 (8) | −0.0036 (8) | | C15 | 0.0408 (11) | 0.0315 (11) | 0.0359 (10) | −0.0118 (9) | 0.0098 (8) | −0.0126 (9) | | C16 | 0.0399 (11) | 0.0382 (12) | 0.0249 (10) | −0.0122 (8) | −0.0022 (8) | 0.0001 (8) | | C17 | 0.0265 (9) | 0.0293 (10) | 0.0275 (9) | −0.0020 (7) | −0.0043 (7) | 0.0047 (7) | | C18 | 0.0179 (7) | 0.0194 (8) | 0.0241 (8) | −0.0010 (6) | 0.0010 (6) | 0.0018 (6) |
Geometric parameters (Å, °) | Zn1—O1 | 1.907 (1) | C7—H7 | 0.994 (9) | | Zn1—O1i | 1.907 (1) | C8—C9 | 1.523 (2) | | Zn1—N1 | 2.016 (1) | C8—H81 | 0.989 (9) | | Zn1—N1i | 2.016 (1) | C8—H82 | 0.994 (10) | | Cl1—C4 | 1.745 (2) | C9—C10 | 1.502 (2) | | O1—C1 | 1.312 (2) | C9—H91 | 0.998 (10) | | N1—C7 | 1.282 (2) | C9—H92 | 1.004 (10) | | N1—C8 | 1.469 (2) | C10—C11 | 1.366 (3) | | C1—C2 | 1.419 (2) | C10—C12 | 1.439 (3) | | C1—C6 | 1.427 (2) | C11—H11 | 0.990 (10) | | N2—C18 | 1.374 (2) | C12—C13 | 1.402 (3) | | N2—C11 | 1.383 (2) | C12—C18 | 1.415 (2) | | N2—H2N | 0.870 (10) | C13—C15 | 1.379 (3) | | C2—C3 | 1.374 (2) | C13—H13 | 0.998 (10) | | C2—H2 | 0.994 (10) | C15—C16 | 1.405 (3) | | C3—C4 | 1.391 (3) | C15—H15 | 0.990 (10) | | C3—H3 | 1.001 (10) | C16—C17 | 1.382 (3) | | C4—C5 | 1.370 (2) | C16—H16 | 0.992 (10) | | C5—C6 | 1.410 (2) | C17—C18 | 1.398 (2) | | C5—H5 | 0.999 (10) | C17—H17 | 0.996 (10) | | C6—C7 | 1.453 (2) | | | | | | | | O1—Zn1—O1i | 116.62 (8) | N1—C8—H81 | 108.7 (12) | | O1—Zn1—N1 | 95.57 (5) | C9—C8—H81 | 109.5 (12) | | O1—Zn1—N1i | 125.55 (6) | N1—C8—H82 | 109.4 (14) | | O1i—Zn1—N1 | 125.55 (6) | C9—C8—H82 | 110.3 (13) | | O1i—Zn1—N1i | 95.57 (5) | H81—C8—H82 | 107.8 (18) | | N1—Zn1—N1i | 99.56 (8) | C10—C9—C8 | 110.87 (15) | | C1—O1—Zn1 | 124.38 (11) | C10—C9—H91 | 109.5 (17) | | C7—N1—C8 | 118.25 (14) | C8—C9—H91 | 109.0 (16) | | C7—N1—Zn1 | 120.68 (11) | C10—C9—H92 | 110.3 (16) | | C8—N1—Zn1 | 119.96 (10) | C8—C9—H92 | 110.3 (15) | | O1—C1—C2 | 118.25 (15) | H91—C9—H92 | 107 (2) | | O1—C1—C6 | 124.63 (15) | C11—C10—C12 | 106.68 (16) | | C2—C1—C6 | 117.12 (14) | C11—C10—C9 | 127.04 (19) | | C18—N2—C11 | 109.06 (15) | C12—C10—C9 | 126.20 (17) | | C18—N2—H2N | 125.3 (18) | C10—C11—N2 | 109.81 (16) | | C11—N2—H2N | 125.7 (18) | C10—C11—H11 | 129.7 (14) | | C3—C2—C1 | 122.28 (16) | N2—C11—H11 | 120.4 (14) | | C3—C2—H2 | 118.2 (14) | C13—C12—C18 | 118.94 (17) | | C1—C2—H2 | 119.6 (14) | C13—C12—C10 | 134.06 (17) | | C2—C3—C4 | 119.47 (15) | C18—C12—C10 | 106.99 (15) | | C2—C3—H3 | 119.0 (14) | C15—C13—C12 | 118.76 (19) | | C4—C3—H3 | 121.5 (14) | C15—C13—H13 | 120.0 (14) | | C5—C4—C3 | 120.68 (16) | C12—C13—H13 | 121.2 (14) | | C5—C4—Cl1 | 119.65 (14) | C13—C15—C16 | 121.40 (19) | | C3—C4—Cl1 | 119.66 (13) | C13—C15—H15 | 118.7 (15) | | C4—C5—C6 | 120.98 (16) | C16—C15—H15 | 119.8 (15) | | C4—C5—H5 | 118.2 (14) | C17—C16—C15 | 121.4 (2) | | C6—C5—H5 | 120.8 (14) | C17—C16—H16 | 120.4 (16) | | C5—C6—C1 | 119.38 (14) | C15—C16—H16 | 118.2 (16) | | C5—C6—C7 | 115.93 (14) | C16—C17—C18 | 117.02 (18) | | C1—C6—C7 | 124.69 (14) | C16—C17—H17 | 121.9 (15) | | N1—C7—C6 | 126.44 (15) | C18—C17—H17 | 121.1 (15) | | N1—C7—H7 | 118.8 (12) | N2—C18—C17 | 130.10 (17) | | C6—C7—H7 | 114.6 (12) | N2—C18—C12 | 107.45 (15) | | N1—C8—C9 | 111.15 (14) | C17—C18—C12 | 122.43 (17) | | | | | | O1i—Zn1—O1—C1 | 153.77 (15) | C1—C6—C7—N1 | 2.3 (3) | | N1—Zn1—O1—C1 | 19.16 (14) | C7—N1—C8—C9 | 104.80 (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—C10 | 169.91 (16) | | O1i—Zn1—N1—C7 | −147.38 (12) | C8—C9—C10—C11 | 79.8 (2) | | N1i—Zn1—N1—C7 | 108.67 (14) | C8—C9—C10—C12 | −96.6 (2) | | O1—Zn1—N1—C8 | 173.41 (12) | C12—C10—C11—N2 | −0.1 (2) | | O1i—Zn1—N1—C8 | 44.87 (14) | C9—C10—C11—N2 | −177.12 (16) | | N1i—Zn1—N1—C8 | −59.09 (10) | C18—N2—C11—C10 | 0.3 (2) | | Zn1—O1—C1—C2 | 167.80 (12) | C11—C10—C12—C13 | 178.99 (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—C3 | 2.7 (3) | C9—C10—C12—C18 | 176.96 (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—Cl1 | 177.25 (14) | C12—C13—C15—C16 | 0.4 (3) | | C3—C4—C5—C6 | 1.8 (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—C1 | 0.5 (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—C5 | 176.72 (16) | C16—C17—C18—N2 | 178.95 (18) | | C2—C1—C6—C5 | −2.7 (2) | C16—C17—C18—C12 | 0.7 (3) | | O1—C1—C6—C7 | −2.9 (3) | C13—C12—C18—N2 | −178.99 (16) | | C2—C1—C6—C7 | 177.69 (15) | C10—C12—C18—N2 | 0.22 (19) | | C8—N1—C7—C6 | 179.43 (15) | C13—C12—C18—C17 | −0.4 (3) | | Zn1—N1—C7—C6 | 11.5 (2) | C10—C12—C18—C17 | 178.85 (16) | | C5—C6—C7—N1 | −177.31 (16) | | |
Symmetry codes: (i) −x+1, y, −z+3/2. - Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
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- Chen, J., Xu, X.-Y., Gao, J., Li, Y.-H. & Xu, G.-X. (2007). Chin. J. Struct. Chem.26, 632–636.
- Ng, S. W. (2008). Private communication (deposition number: 67380). CCDC, Cambridge, England.
- Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
- Westrip, S. P. (2008). publCIF In preparation.
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