Dichlorido{2-morpholino-N-[1-(2-pyrid­yl)ethyl­idene]ethanamine-κ3N,N′,N′′}zinc(II)

Ikmal Hisham, N.A.; Suleiman Gwaram, N.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536810050671

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page m55

https://doi.org/10.1107/S1600536810050671

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Dichlorido{2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³N,N′,N′′}zinc(II)

Nurul Azimah Ikmal Hisham,^a Nura Suleiman Gwaram,^a Hamid Khaledi ^a ^* and Hapipah Mohd Ali ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 30 November 2010; accepted 3 December 2010; online 11 December 2010)

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 Zn^II 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 crystal structure of an analogous Cd^II complex, see: Ikmal Hisham et al. (2010 ). For crystal structures of similar Zn^II complexes, see: Chattopadhyay et al. (2009 ); Sun (2005 ).

Experimental

Crystal data

[ZnCl₂(C₁₃H₁₉N₃O)]
M_r = 369.58
Monoclinic, P 2₁ /n
a = 9.5737 (12) Å
b = 13.7064 (17) Å
c = 12.0766 (15) Å
β = 106.643 (2)°
V = 1518.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.97 mm⁻¹
T = 100 K
0.35 × 0.21 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.546, T_max = 0.908
13693 measured reflections
2979 independent reflections
2552 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.091
S = 1.08
2979 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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⋯Cl1^iv	0.99	2.88	3.665 (3)	137
C7—H7B⋯Cl1ⁱ	0.98	2.85	3.807 (3)	166
C8—H8A⋯Cl2^iv	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) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810050671/pv2366sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050671/pv2366Isup2.hkl

checkCIF report

Comment top

The title compound is isostructural with the analogous Cd^II complex (Ikmal Hisham et al., 2010). The Schiff base, 2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine and two Cl atoms coordinate the Zn^II 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.

Related literature top

For the crystal structure of an analogous Cd^II complex, see: Ikmal Hisham et al. (2010). For crystal structures of similar Zn^II complexes, see: Chattopadhyay et al. (2009); Sun (2005).

Experimental top

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.

Structure description top

For the crystal structure of an analogous Cd^II complex, see: Ikmal Hisham et al. (2010). For crystal structures of similar Zn^II complexes, see: Chattopadhyay et al. (2009); Sun (2005).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: 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).

Figures top

Fig. 1. Displacement ellipsoid plot of the title compound at the 50% probability level. G atoms are drawn as spheres of arbitrary radius.

Dichlorido{2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine- κ³N,N',N''}zinc(II) top

Crystal data top

[ZnCl₂(C₁₃H₁₉N₃O)]	F(000) = 760
M_r = 369.58	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	2979 independent reflections
Radiation source: fine-focus sealed tube	2552 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
φ and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.546, T_max = 0.908	k = −16→16
13693 measured reflections	l = −14→14

Refinement top

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(F_o²) + (0.0515P)² + 0.4492P] where P = (F_o² + 2F_c²)/3
2979 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 1.03 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[ZnCl₂(C₁₃H₁₉N₃O)]	V = 1518.3 (3) Å³
M_r = 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)°

Data collection top

Bruker APEXII CCD diffractometer	2979 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2552 reflections with I > 2σ(I)
T_min = 0.546, T_max = 0.908	R_int = 0.047
13693 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.08	Δρ_max = 1.03 e Å⁻³
2979 reflections	Δρ_min = −0.39 e Å⁻³
182 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···Cl1^iv	0.99	2.88	3.665 (3)	137
C7—H7B···Cl1ⁱ	0.98	2.85	3.807 (3)	166
C8—H8A···Cl2^iv	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)]
M_r	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)
T_min, T_max	0.546, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	13693, 2979, 2552
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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···Cl1^iv	0.99	2.88	3.665 (3)	137
C7—H7B···Cl1ⁱ	0.98	2.85	3.807 (3)	166
C8—H8A···Cl2^iv	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).

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