metal-organic compounds
Dichlorido{2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine-κ3N,N′,N′′}zinc(II)
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: khaledi@siswa.um.edu.my
In the title compound, [ZnCl2(C13H19N3O)], the Schiff base ligand acts as an N,N′,N′′-tridentate chelating agent, making two five-membered rings with the ZnII ion. The metal atom is five-coordinated by the Schiff base ligand and two Cl atoms in a distorted square-pyramidal geometry. An intramolecular C—H⋯Cl interaction occurs. In the crystal, adjacent molecules are linked together via C—H⋯Cl hydrogen-bonding and long range C—H⋯O and C—H⋯Cl interactions into a three-dimensional network.
Related literature
For the II complex, see: Ikmal Hisham et al. (2010). For crystal structures of similar ZnII complexes, see: Chattopadhyay et al. (2009); Sun (2005).
of an analogous CdExperimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536810050671/pv2366sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050671/pv2366Isup2.hkl
A mixture of 2-acetylpyridine (0.20 g, 1.65 mmol) and 4-(2-aminoethyl)morpholine (0.21 g, 1.65 mmol) in the presence of a few drops of HCl (37%) in ethanol (20 ml) was refluxed. After 2 hr a solution of zinc(II) acetate dihydrate (0.36 g, 1.65 mmol) in a minimum amount of water was added and the resulting solution was refluxed for 30 min, then set aside at room temperature. The crystals of the title complex were obtained after a few days.
The hydrogen atoms were placed at calculated positions (C—H 0.95 - 0.99 Å) and were treated as riding on their parent atoms with U(H) set to 1.2–1.5 Ueq(C). The final difference map was essentially featurless with residual electron density close to the metal atom.
The title compound is isostructural with the analogous CdII complex (Ikmal Hisham et al., 2010). The Schiff base, 2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine and two Cl atoms coordinate the ZnII ion in a distorted square-pyramidal geometry (τ = 0.22). The Zn—Cl and Zn—N bond lengths in the structure are in agreement with the values reported in the literature (Chattopadhyay et al., 2009; Sun, 2005). In the intermolecular C—H···Cl hydrogen bonding and long range C—H···O and C—H···Cl interactions link the adjacent molecules into a three-dimensional network. An intramolecular C—H···Cl hydrogen bonding has also been observed.
For the
of an analogous CdII complex, see: Ikmal Hisham et al. (2010). For crystal structures of similar ZnII complexes, see: Chattopadhyay et al. (2009); Sun (2005).Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).Fig. 1. Displacement ellipsoid plot of the title compound at the 50% probability level. G atoms are drawn as spheres of arbitrary radius. |
[ZnCl2(C13H19N3O)] | F(000) = 760 |
Mr = 369.58 | Dx = 1.617 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3471 reflections |
a = 9.5737 (12) Å | θ = 2.3–27.5° |
b = 13.7064 (17) Å | µ = 1.97 mm−1 |
c = 12.0766 (15) Å | T = 100 K |
β = 106.643 (2)° | Plate, yellow |
V = 1518.3 (3) Å3 | 0.35 × 0.21 × 0.05 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 2979 independent reflections |
Radiation source: fine-focus sealed tube | 2552 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.546, Tmax = 0.908 | k = −16→16 |
13693 measured reflections | l = −14→14 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0515P)2 + 0.4492P] where P = (Fo2 + 2Fc2)/3 |
2979 reflections | (Δ/σ)max = 0.001 |
182 parameters | Δρmax = 1.03 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
[ZnCl2(C13H19N3O)] | V = 1518.3 (3) Å3 |
Mr = 369.58 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.5737 (12) Å | µ = 1.97 mm−1 |
b = 13.7064 (17) Å | T = 100 K |
c = 12.0766 (15) Å | 0.35 × 0.21 × 0.05 mm |
β = 106.643 (2)° |
Bruker APEXII CCD diffractometer | 2979 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2552 reflections with I > 2σ(I) |
Tmin = 0.546, Tmax = 0.908 | Rint = 0.047 |
13693 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.08 | Δρmax = 1.03 e Å−3 |
2979 reflections | Δρmin = −0.39 e Å−3 |
182 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.72733 (3) | 0.08854 (2) | 0.16005 (3) | 0.01368 (12) | |
Cl1 | 0.95230 (7) | 0.13655 (5) | 0.26836 (6) | 0.01677 (16) | |
Cl2 | 0.54542 (7) | 0.19943 (5) | 0.13205 (6) | 0.01828 (17) | |
O1 | 0.6851 (2) | 0.06197 (15) | 0.51473 (16) | 0.0224 (4) | |
N1 | 0.7630 (2) | 0.11923 (16) | −0.01195 (19) | 0.0156 (5) | |
N2 | 0.7468 (2) | −0.04614 (15) | 0.08710 (18) | 0.0145 (5) | |
N3 | 0.6560 (2) | −0.01499 (15) | 0.28543 (18) | 0.0146 (5) | |
C1 | 0.7536 (3) | 0.20493 (19) | −0.0655 (2) | 0.0183 (6) | |
H1 | 0.7219 | 0.2601 | −0.0317 | 0.022* | |
C2 | 0.7881 (3) | 0.2169 (2) | −0.1689 (2) | 0.0208 (6) | |
H2 | 0.7788 | 0.2788 | −0.2057 | 0.025* | |
C3 | 0.8363 (3) | 0.1366 (2) | −0.2170 (2) | 0.0191 (6) | |
H3 | 0.8633 | 0.1430 | −0.2865 | 0.023* | |
C4 | 0.8449 (3) | 0.0468 (2) | −0.1625 (2) | 0.0172 (6) | |
H4 | 0.8764 | −0.0095 | −0.1946 | 0.021* | |
C5 | 0.8064 (3) | 0.04073 (18) | −0.0604 (2) | 0.0147 (6) | |
C6 | 0.7974 (3) | −0.05297 (19) | 0.0006 (2) | 0.0148 (6) | |
C7 | 0.8414 (3) | −0.14742 (19) | −0.0420 (2) | 0.0178 (6) | |
H7A | 0.8954 | −0.1870 | 0.0240 | 0.027* | |
H7B | 0.9034 | −0.1342 | −0.0922 | 0.027* | |
H7C | 0.7541 | −0.1829 | −0.0856 | 0.027* | |
C8 | 0.7172 (3) | −0.13162 (19) | 0.1493 (2) | 0.0186 (6) | |
H8A | 0.8078 | −0.1542 | 0.2064 | 0.022* | |
H8B | 0.6782 | −0.1856 | 0.0947 | 0.022* | |
C9 | 0.6064 (3) | −0.10075 (19) | 0.2097 (2) | 0.0184 (6) | |
H9A | 0.5134 | −0.0847 | 0.1511 | 0.022* | |
H9B | 0.5879 | −0.1558 | 0.2567 | 0.022* | |
C10 | 0.5308 (3) | 0.0196 (2) | 0.3241 (2) | 0.0181 (6) | |
H10A | 0.4885 | −0.0360 | 0.3557 | 0.022* | |
H10B | 0.4546 | 0.0459 | 0.2570 | 0.022* | |
C11 | 0.5765 (3) | 0.0979 (2) | 0.4155 (2) | 0.0217 (6) | |
H11A | 0.6157 | 0.1546 | 0.3833 | 0.026* | |
H11B | 0.4905 | 0.1200 | 0.4386 | 0.026* | |
C12 | 0.8104 (3) | 0.0335 (2) | 0.4810 (2) | 0.0208 (6) | |
H12A | 0.8865 | 0.0092 | 0.5495 | 0.025* | |
H12B | 0.8501 | 0.0910 | 0.4507 | 0.025* | |
C13 | 0.7736 (3) | −0.0452 (2) | 0.3896 (2) | 0.0197 (6) | |
H13A | 0.8621 | −0.0616 | 0.3666 | 0.024* | |
H13B | 0.7425 | −0.1046 | 0.4226 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.01259 (19) | 0.01472 (18) | 0.01459 (18) | −0.00019 (11) | 0.00529 (13) | −0.00150 (11) |
Cl1 | 0.0128 (3) | 0.0199 (3) | 0.0179 (3) | −0.0021 (2) | 0.0048 (3) | −0.0023 (2) |
Cl2 | 0.0152 (3) | 0.0206 (3) | 0.0194 (3) | 0.0037 (3) | 0.0056 (3) | 0.0007 (2) |
O1 | 0.0203 (11) | 0.0347 (11) | 0.0144 (10) | 0.0023 (9) | 0.0085 (9) | 0.0005 (8) |
N1 | 0.0126 (12) | 0.0185 (11) | 0.0154 (11) | −0.0004 (9) | 0.0037 (9) | 0.0002 (9) |
N2 | 0.0138 (12) | 0.0159 (11) | 0.0133 (11) | −0.0016 (9) | 0.0030 (9) | −0.0005 (9) |
N3 | 0.0142 (12) | 0.0156 (11) | 0.0145 (11) | −0.0015 (9) | 0.0051 (9) | −0.0004 (9) |
C1 | 0.0172 (14) | 0.0179 (13) | 0.0186 (14) | −0.0009 (11) | 0.0033 (12) | −0.0023 (10) |
C2 | 0.0228 (16) | 0.0228 (14) | 0.0146 (13) | −0.0042 (12) | 0.0019 (12) | 0.0021 (10) |
C3 | 0.0148 (14) | 0.0292 (15) | 0.0135 (13) | −0.0032 (12) | 0.0044 (11) | −0.0010 (11) |
C4 | 0.0108 (14) | 0.0222 (14) | 0.0186 (14) | −0.0002 (11) | 0.0044 (11) | −0.0034 (11) |
C5 | 0.0119 (13) | 0.0168 (13) | 0.0137 (13) | −0.0013 (10) | 0.0010 (11) | −0.0018 (10) |
C6 | 0.0099 (13) | 0.0187 (13) | 0.0139 (13) | −0.0015 (10) | 0.0005 (11) | −0.0010 (10) |
C7 | 0.0171 (14) | 0.0179 (13) | 0.0201 (14) | −0.0003 (11) | 0.0081 (12) | −0.0026 (10) |
C8 | 0.0248 (16) | 0.0147 (13) | 0.0174 (14) | −0.0013 (11) | 0.0077 (12) | 0.0003 (10) |
C9 | 0.0171 (15) | 0.0190 (13) | 0.0203 (14) | −0.0056 (11) | 0.0070 (12) | −0.0013 (11) |
C10 | 0.0110 (14) | 0.0257 (15) | 0.0190 (14) | −0.0028 (11) | 0.0065 (11) | 0.0018 (11) |
C11 | 0.0212 (16) | 0.0268 (15) | 0.0196 (15) | 0.0055 (12) | 0.0099 (13) | 0.0007 (11) |
C12 | 0.0113 (14) | 0.0355 (16) | 0.0149 (13) | −0.0003 (12) | 0.0028 (11) | 0.0017 (12) |
C13 | 0.0166 (15) | 0.0231 (14) | 0.0194 (14) | 0.0026 (11) | 0.0052 (12) | 0.0039 (11) |
Zn1—N2 | 2.077 (2) | C4—H4 | 0.9500 |
Zn1—N1 | 2.239 (2) | C5—C6 | 1.495 (4) |
Zn1—Cl2 | 2.2628 (7) | C6—C7 | 1.497 (4) |
Zn1—Cl1 | 2.2736 (7) | C7—H7A | 0.9800 |
Zn1—N3 | 2.316 (2) | C7—H7B | 0.9800 |
O1—C12 | 1.427 (3) | C7—H7C | 0.9800 |
O1—C11 | 1.430 (3) | C8—C9 | 1.510 (4) |
N1—C1 | 1.331 (3) | C8—H8A | 0.9900 |
N1—C5 | 1.346 (3) | C8—H8B | 0.9900 |
N2—C6 | 1.274 (3) | C9—H9A | 0.9900 |
N2—C8 | 1.463 (3) | C9—H9B | 0.9900 |
N3—C9 | 1.482 (3) | C10—C11 | 1.511 (4) |
N3—C10 | 1.484 (3) | C10—H10A | 0.9900 |
N3—C13 | 1.487 (3) | C10—H10B | 0.9900 |
C1—C2 | 1.390 (4) | C11—H11A | 0.9900 |
C1—H1 | 0.9500 | C11—H11B | 0.9900 |
C2—C3 | 1.384 (4) | C12—C13 | 1.511 (4) |
C2—H2 | 0.9500 | C12—H12A | 0.9900 |
C3—C4 | 1.387 (4) | C12—H12B | 0.9900 |
C3—H3 | 0.9500 | C13—H13A | 0.9900 |
C4—C5 | 1.387 (4) | C13—H13B | 0.9900 |
N2—Zn1—N1 | 73.58 (8) | C6—C7—H7B | 109.5 |
N2—Zn1—Cl2 | 133.83 (6) | H7A—C7—H7B | 109.5 |
N1—Zn1—Cl2 | 92.90 (6) | C6—C7—H7C | 109.5 |
N2—Zn1—Cl1 | 108.41 (6) | H7A—C7—H7C | 109.5 |
N1—Zn1—Cl1 | 96.22 (6) | H7B—C7—H7C | 109.5 |
Cl2—Zn1—Cl1 | 116.95 (3) | N2—C8—C9 | 106.9 (2) |
N2—Zn1—N3 | 79.16 (8) | N2—C8—H8A | 110.4 |
N1—Zn1—N3 | 150.85 (8) | C9—C8—H8A | 110.4 |
Cl2—Zn1—N3 | 98.68 (6) | N2—C8—H8B | 110.4 |
Cl1—Zn1—N3 | 102.08 (6) | C9—C8—H8B | 110.4 |
C12—O1—C11 | 108.9 (2) | H8A—C8—H8B | 108.6 |
C1—N1—C5 | 118.7 (2) | N3—C9—C8 | 112.0 (2) |
C1—N1—Zn1 | 127.53 (19) | N3—C9—H9A | 109.2 |
C5—N1—Zn1 | 113.63 (17) | C8—C9—H9A | 109.2 |
C6—N2—C8 | 122.5 (2) | N3—C9—H9B | 109.2 |
C6—N2—Zn1 | 120.96 (18) | C8—C9—H9B | 109.2 |
C8—N2—Zn1 | 116.09 (17) | H9A—C9—H9B | 107.9 |
C9—N3—C10 | 107.6 (2) | N3—C10—C11 | 111.5 (2) |
C9—N3—C13 | 109.5 (2) | N3—C10—H10A | 109.3 |
C10—N3—C13 | 107.9 (2) | C11—C10—H10A | 109.3 |
C9—N3—Zn1 | 100.66 (15) | N3—C10—H10B | 109.3 |
C10—N3—Zn1 | 115.21 (16) | C11—C10—H10B | 109.3 |
C13—N3—Zn1 | 115.49 (16) | H10A—C10—H10B | 108.0 |
N1—C1—C2 | 122.7 (3) | O1—C11—C10 | 110.9 (2) |
N1—C1—H1 | 118.7 | O1—C11—H11A | 109.5 |
C2—C1—H1 | 118.7 | C10—C11—H11A | 109.5 |
C3—C2—C1 | 118.5 (3) | O1—C11—H11B | 109.5 |
C3—C2—H2 | 120.8 | C10—C11—H11B | 109.5 |
C1—C2—H2 | 120.8 | H11A—C11—H11B | 108.1 |
C2—C3—C4 | 119.2 (3) | O1—C12—C13 | 111.4 (2) |
C2—C3—H3 | 120.4 | O1—C12—H12A | 109.4 |
C4—C3—H3 | 120.4 | C13—C12—H12A | 109.4 |
C3—C4—C5 | 118.7 (3) | O1—C12—H12B | 109.4 |
C3—C4—H4 | 120.6 | C13—C12—H12B | 109.4 |
C5—C4—H4 | 120.6 | H12A—C12—H12B | 108.0 |
N1—C5—C4 | 122.1 (2) | N3—C13—C12 | 112.4 (2) |
N1—C5—C6 | 113.8 (2) | N3—C13—H13A | 109.1 |
C4—C5—C6 | 123.9 (2) | C12—C13—H13A | 109.1 |
N2—C6—C5 | 115.5 (2) | N3—C13—H13B | 109.1 |
N2—C6—C7 | 123.8 (2) | C12—C13—H13B | 109.1 |
C5—C6—C7 | 120.8 (2) | H13A—C13—H13B | 107.9 |
C6—C7—H7A | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cl1i | 0.95 | 2.71 | 3.625 (3) | 161 |
C7—H7C···Cl2ii | 0.98 | 2.77 | 3.619 (3) | 146 |
C12—H12B···Cl1 | 0.99 | 2.73 | 3.526 (3) | 138 |
C10—H10A···O1iii | 0.99 | 2.61 | 3.408 (3) | 137 |
C9—H9B···Cl1iv | 0.99 | 2.88 | 3.665 (3) | 137 |
C7—H7B···Cl1i | 0.98 | 2.85 | 3.807 (3) | 166 |
C8—H8A···Cl2iv | 0.99 | 2.87 | 3.750 (3) | 149 |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z; (iii) −x+1, −y, −z+1; (iv) −x+3/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [ZnCl2(C13H19N3O)] |
Mr | 369.58 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 9.5737 (12), 13.7064 (17), 12.0766 (15) |
β (°) | 106.643 (2) |
V (Å3) | 1518.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.97 |
Crystal size (mm) | 0.35 × 0.21 × 0.05 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.546, 0.908 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13693, 2979, 2552 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.091, 1.08 |
No. of reflections | 2979 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.03, −0.39 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXL97 and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cl1i | 0.95 | 2.71 | 3.625 (3) | 161 |
C7—H7C···Cl2ii | 0.98 | 2.77 | 3.619 (3) | 146 |
C12—H12B···Cl1 | 0.99 | 2.73 | 3.526 (3) | 138 |
C10—H10A···O1iii | 0.99 | 2.61 | 3.408 (3) | 137 |
C9—H9B···Cl1iv | 0.99 | 2.88 | 3.665 (3) | 137 |
C7—H7B···Cl1i | 0.98 | 2.85 | 3.807 (3) | 166 |
C8—H8A···Cl2iv | 0.99 | 2.87 | 3.750 (3) | 149 |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z; (iii) −x+1, −y, −z+1; (iv) −x+3/2, y−1/2, −z+1/2. |
Acknowledgements
The authors thank University of Malaya for funding this study (UMRG grant RG024/09BIO).
References
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The title compound is isostructural with the analogous CdII complex (Ikmal Hisham et al., 2010). The Schiff base, 2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine and two Cl atoms coordinate the ZnII ion in a distorted square-pyramidal geometry (τ = 0.22). The Zn—Cl and Zn—N bond lengths in the structure are in agreement with the values reported in the literature (Chattopadhyay et al., 2009; Sun, 2005). In the crystal structure, intermolecular C—H···Cl hydrogen bonding and long range C—H···O and C—H···Cl interactions link the adjacent molecules into a three-dimensional network. An intramolecular C—H···Cl hydrogen bonding has also been observed.