{N,N′-Bis[(E)-3-phenyl­allyl­idene]ethane-1,2-diamine}dichloridozinc(II)

Cai, H.-L.; Liu, B.; Lin, Z.-D.

doi:10.1107/S1600536808037860

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1597

doi:10.1107/S1600536808037860

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{N,N′-Bis[(E)-3-phenylallylidene]ethane-1,2-diamine}dichloridozinc(II)

Hong-Lan Cai,^a ^* Bing Liu ^a and Zhi-Dong Lin ^b

^aSchool of Chemistry and Materials Science, Ludong University, Shandong 264025, People's Republic of China, and ^bSchool of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430073, People's Republic of China
^*Correspondence e-mail: honglancai74@126.com

(Received 11 October 2008; accepted 14 November 2008; online 22 November 2008)

In the title compound, [ZnCl₂(C₂₀H₂₀N₂)], the Zn^II atom is four coordinated in a distorted tetrahedral geometry by two N atoms of the Schiff base ligand and by two Cl atoms. Edge-to-face C—H⋯π interactions exist between molecules, with a dihedral angle of 37.8 (1)° between the benzene ring planes and a shortest H⋯centroid distance of 3.62 (5) Å.

Related literature

For related literature on transition metal complexes of Schiff base ligands, see: Bhatia et al. (1981 ); Costamagna et al. (1992 ). For related complexes of ZnCl₂ with bidentate ligands, see: Tolman et al. (1991 ); Wang et al. (2007 ).

Experimental

Crystal data

[ZnCl₂(C₂₀H₂₀N₂)]
M_r = 424.65
Monoclinic, P 2₁ /c
a = 7.2140 (8) Å
b = 20.265 (2) Å
c = 14.0906 (16) Å
β = 94.913 (2)°
V = 2052.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.46 mm⁻¹
T = 300 (2) K
0.23 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.730, T_max = 0.868
15814 measured reflections
4458 independent reflections
3027 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.132
S = 0.99
4458 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037860/bi2311sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037860/bi2311Isup2.hkl

checkCIF report

Comment top

Transition-metal compounds containing Schiff-base ligands play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures (Costamagna et al., 1992; Bhatia et al., 1981). In the title compound (Fig. 1), the Zn^II atom is coordinated by a bidentate Schiff-base ligand and two Cl atoms in a slightly distorted tetrahedral geometry. The Zn—Cl bond distances are comparable to those observed in the related compounds [ZnCl₂(C₁₂H₁₆BrClN₂O)] (Wang et al., 2007) and [ZnCl₂(C₁₆H₁₈N₄O)] (Tolman et al., 1991).

Related literature top

For related literature on transition metal complexes of Schiff base ligands, see: Bhatia et al. (1981); Costamagna et al. (1992). For related complexes of ZnCl₂ with bidentate ligands, see: Tolman et al. (1991); Wang et al. (2007).

Experimental top

Cinnamaldehyde (0.2 mmol, 26.4 mg), ZnCl₂.6H₂O (0.1 mmol, 24 mg) and ethylenediamine (0.1 mmol, 6.4 mg) were dissolved in methanol (10 ml). The mixture was stirred for 30 min at room temperature to give a clear yellow solution, which was left in air for a few days to give yellow crystals of the title compound (yield 79%). Elemental analysis calculated: C 56.56, H 4.75, N 6.60%; found: C 56.79, H 4.49, N 6.31%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure with displacement ellipsoids drawn at 50% probability for non-H atoms.
	Fig. 2. Packing diagram viewed along the a axis.

{N,N'-Bis[(E)-3-phenylallylidene]ethane-1,2-diamine} dichloridozinc(II) top

Crystal data top

[ZnCl₂(C₂₀H₂₀N₂)]	F(000) = 872
M_r = 424.65	D_x = 1.374 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 553 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.2140 (8) Å	Cell parameters from 2760 reflections
b = 20.265 (2) Å	θ = 2.1–28.1°
c = 14.0906 (16) Å	µ = 1.46 mm⁻¹
β = 94.913 (2)°	T = 300 K
V = 2052.4 (4) Å³	Block, yellow
Z = 4	0.23 × 0.20 × 0.10 mm

Data collection top

Bruker SMART CCD diffractometer	4458 independent reflections
Radiation source: fine-focus sealed tube	3027 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −9→9
T_min = 0.730, T_max = 0.868	k = −25→24
15814 measured reflections	l = −17→12

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0805P)²] where P = (F_o² + 2F_c²)/3
4458 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[ZnCl₂(C₂₀H₂₀N₂)]	V = 2052.4 (4) Å³
M_r = 424.65	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.2140 (8) Å	µ = 1.46 mm⁻¹
b = 20.265 (2) Å	T = 300 K
c = 14.0906 (16) Å	0.23 × 0.20 × 0.10 mm
β = 94.913 (2)°

Data collection top

Bruker SMART CCD diffractometer	4458 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	3027 reflections with I > 2σ(I)
T_min = 0.730, T_max = 0.868	R_int = 0.030
15814 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 0.99	Δρ_max = 0.50 e Å⁻³
4458 reflections	Δρ_min = −0.29 e Å⁻³
226 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	0.09704 (4)	0.575283 (15)	0.83248 (3)	0.06115 (16)
C1	0.2380 (5)	0.84830 (15)	0.8767 (2)	0.0731 (8)
C2	0.2309 (7)	0.91286 (17)	0.9108 (3)	0.0965 (13)
H2	0.1260	0.9274	0.9387	0.116*
C3	0.3789 (9)	0.9553 (2)	0.9034 (4)	0.1214 (18)
H3	0.3736	0.9982	0.9264	0.146*
C4	0.5311 (10)	0.9345 (3)	0.8629 (4)	0.1234 (19)
H4	0.6303	0.9633	0.8585	0.148*
C5	0.5423 (6)	0.8711 (2)	0.8278 (3)	0.1013 (12)
H5	0.6482	0.8574	0.8000	0.122*
C6	0.3962 (5)	0.82863 (17)	0.8343 (2)	0.0822 (9)
H6	0.4029	0.7861	0.8100	0.099*
C7	0.0772 (4)	0.80522 (15)	0.8855 (2)	0.0706 (8)
H7	−0.0286	0.8250	0.9060	0.085*
C8	0.0665 (4)	0.74079 (14)	0.8672 (2)	0.0674 (8)
H8	0.1705	0.7195	0.8471	0.081*
C9	−0.0972 (4)	0.70302 (14)	0.8772 (2)	0.0637 (7)
H9	−0.2026	0.7248	0.8947	0.076*
C10	−0.2802 (4)	0.60569 (14)	0.8766 (2)	0.0694 (8)
H10A	−0.3857	0.6348	0.8626	0.083*
H10B	−0.2803	0.5912	0.9422	0.083*
C11	−0.2957 (4)	0.54701 (14)	0.8112 (2)	0.0673 (8)
H11A	−0.3980	0.5190	0.8267	0.081*
H11B	−0.3194	0.5615	0.7457	0.081*
C12	−0.1214 (4)	0.44778 (15)	0.8336 (2)	0.0630 (7)
H12	−0.2364	0.4268	0.8300	0.076*
C13	0.0416 (4)	0.40785 (14)	0.8503 (2)	0.0624 (7)
H13	0.1578	0.4280	0.8537	0.075*
C14	0.0320 (4)	0.34316 (14)	0.8611 (2)	0.0661 (7)
H14	−0.0874	0.3255	0.8544	0.079*
C15	0.1802 (5)	0.29590 (14)	0.8818 (2)	0.0685 (8)
C16	0.1377 (6)	0.22894 (16)	0.8800 (2)	0.0884 (10)
H16	0.0154	0.2152	0.8660	0.106*
C17	0.2773 (10)	0.1826 (2)	0.8991 (3)	0.1219 (18)
H17	0.2477	0.1380	0.8977	0.146*
C18	0.4567 (9)	0.2015 (3)	0.9198 (3)	0.131 (2)
H18	0.5496	0.1700	0.9307	0.158*
C19	0.5004 (6)	0.2675 (3)	0.9245 (3)	0.1094 (14)
H19	0.6228	0.2803	0.9405	0.131*
C20	0.3652 (5)	0.31469 (18)	0.9059 (2)	0.0784 (9)
H20	0.3967	0.3592	0.9093	0.094*
Cl1	0.20858 (16)	0.59354 (5)	0.69366 (8)	0.1081 (4)
Cl2	0.30022 (11)	0.55861 (5)	0.95630 (7)	0.0897 (3)
N1	−0.1064 (3)	0.64122 (11)	0.86341 (17)	0.0614 (6)
N2	−0.1194 (3)	0.51002 (10)	0.82321 (16)	0.0593 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0504 (2)	0.0597 (2)	0.0751 (3)	0.00295 (13)	0.01574 (16)	0.00885 (15)
C1	0.096 (2)	0.0645 (18)	0.0562 (18)	−0.0083 (16)	−0.0095 (16)	0.0046 (14)
C2	0.141 (4)	0.070 (2)	0.074 (3)	−0.011 (2)	−0.012 (2)	−0.0016 (17)
C3	0.186 (6)	0.079 (3)	0.091 (3)	−0.042 (3)	−0.033 (3)	0.002 (2)
C4	0.158 (5)	0.115 (4)	0.088 (3)	−0.066 (3)	−0.040 (3)	0.030 (3)
C5	0.104 (3)	0.116 (3)	0.081 (3)	−0.037 (2)	−0.015 (2)	0.021 (2)
C6	0.088 (2)	0.084 (2)	0.073 (2)	−0.0153 (19)	−0.0024 (18)	0.0062 (18)
C7	0.079 (2)	0.0661 (18)	0.066 (2)	0.0042 (15)	0.0032 (15)	−0.0019 (15)
C8	0.0682 (18)	0.0607 (18)	0.074 (2)	0.0033 (13)	0.0079 (15)	0.0016 (15)
C9	0.0599 (17)	0.0656 (18)	0.066 (2)	0.0055 (13)	0.0109 (14)	0.0036 (14)
C10	0.0510 (16)	0.0672 (17)	0.093 (2)	−0.0010 (13)	0.0202 (15)	−0.0057 (16)
C11	0.0497 (15)	0.0717 (18)	0.080 (2)	0.0018 (13)	0.0009 (14)	0.0018 (16)
C12	0.0601 (17)	0.0664 (17)	0.0626 (19)	−0.0061 (13)	0.0053 (14)	−0.0033 (14)
C13	0.0569 (16)	0.0596 (16)	0.070 (2)	−0.0013 (12)	0.0027 (14)	−0.0044 (14)
C14	0.0681 (18)	0.0637 (18)	0.0661 (19)	−0.0057 (14)	0.0036 (14)	−0.0026 (14)
C15	0.089 (2)	0.0611 (18)	0.0550 (18)	0.0098 (15)	0.0066 (16)	−0.0031 (14)
C16	0.132 (3)	0.067 (2)	0.064 (2)	0.006 (2)	−0.010 (2)	−0.0051 (16)
C17	0.213 (6)	0.073 (2)	0.075 (3)	0.047 (3)	−0.016 (3)	−0.0095 (19)
C18	0.164 (5)	0.140 (4)	0.088 (3)	0.091 (4)	−0.003 (3)	−0.008 (3)
C19	0.093 (3)	0.159 (4)	0.076 (3)	0.046 (3)	0.006 (2)	0.003 (3)
C20	0.075 (2)	0.091 (2)	0.070 (2)	0.0096 (18)	0.0065 (16)	0.0062 (17)
Cl1	0.1177 (8)	0.1124 (7)	0.1025 (8)	0.0353 (6)	0.0584 (6)	0.0377 (6)
Cl2	0.0556 (5)	0.1233 (7)	0.0894 (6)	−0.0061 (4)	0.0012 (4)	0.0130 (5)
N1	0.0555 (13)	0.0600 (14)	0.0702 (16)	0.0012 (10)	0.0137 (11)	0.0006 (11)
N2	0.0549 (13)	0.0592 (14)	0.0641 (15)	0.0023 (10)	0.0068 (11)	0.0023 (11)

Geometric parameters (Å, º) top

Zn1—N2	2.042 (2)	C10—H10A	0.970
Zn1—N1	2.059 (2)	C10—H10B	0.970
Zn1—Cl2	2.2064 (10)	C11—N2	1.473 (3)
Zn1—Cl1	2.2092 (10)	C11—H11A	0.970
C1—C6	1.391 (4)	C11—H11B	0.970
C1—C2	1.396 (5)	C12—N2	1.270 (3)
C1—C7	1.465 (4)	C12—C13	1.431 (4)
C2—C3	1.382 (6)	C12—H12	0.930
C2—H2	0.930	C13—C14	1.322 (4)
C3—C4	1.348 (7)	C13—H13	0.930
C3—H3	0.930	C14—C15	1.447 (4)
C4—C5	1.381 (7)	C14—H14	0.930
C4—H4	0.930	C15—C16	1.391 (4)
C5—C6	1.370 (5)	C15—C20	1.402 (4)
C5—H5	0.930	C16—C17	1.386 (6)
C6—H6	0.930	C16—H16	0.930
C7—C8	1.332 (4)	C17—C18	1.357 (7)
C7—H7	0.930	C17—H17	0.930
C8—C9	1.424 (4)	C18—C19	1.373 (7)
C8—H8	0.930	C18—H18	0.930
C9—N1	1.268 (3)	C19—C20	1.375 (5)
C9—H9	0.930	C19—H19	0.930
C10—N1	1.471 (3)	C20—H20	0.930
C10—C11	1.503 (4)

N2—Zn1—N1	83.04 (9)	N2—C11—C10	108.3 (2)
N2—Zn1—Cl2	113.83 (7)	N2—C11—H11A	110.0
N1—Zn1—Cl2	111.68 (7)	C10—C11—H11A	110.0
N2—Zn1—Cl1	112.73 (8)	N2—C11—H11B	110.0
N1—Zn1—Cl1	113.52 (7)	C10—C11—H11B	110.0
Cl2—Zn1—Cl1	117.26 (4)	H11A—C11—H11B	108.4
C6—C1—C2	118.2 (4)	N2—C12—C13	124.3 (3)
C6—C1—C7	123.4 (3)	N2—C12—H12	117.8
C2—C1—C7	118.5 (4)	C13—C12—H12	117.8
C3—C2—C1	120.4 (5)	C14—C13—C12	121.9 (3)
C3—C2—H2	119.8	C14—C13—H13	119.0
C1—C2—H2	119.8	C12—C13—H13	119.0
C4—C3—C2	120.0 (5)	C13—C14—C15	129.4 (3)
C4—C3—H3	120.0	C13—C14—H14	115.3
C2—C3—H3	120.0	C15—C14—H14	115.3
C3—C4—C5	121.2 (5)	C16—C15—C20	118.2 (3)
C3—C4—H4	119.4	C16—C15—C14	119.0 (3)
C5—C4—H4	119.4	C20—C15—C14	122.8 (3)
C6—C5—C4	119.4 (5)	C17—C16—C15	120.1 (4)
C6—C5—H5	120.3	C17—C16—H16	119.9
C4—C5—H5	120.3	C15—C16—H16	119.9
C5—C6—C1	120.9 (4)	C18—C17—C16	121.0 (4)
C5—C6—H6	119.6	C18—C17—H17	119.5
C1—C6—H6	119.6	C16—C17—H17	119.5
C8—C7—C1	126.9 (3)	C17—C18—C19	119.7 (4)
C8—C7—H7	116.5	C17—C18—H18	120.1
C1—C7—H7	116.5	C19—C18—H18	120.1
C7—C8—C9	122.9 (3)	C18—C19—C20	120.8 (4)
C7—C8—H8	118.6	C18—C19—H19	119.6
C9—C8—H8	118.6	C20—C19—H19	119.6
N1—C9—C8	123.3 (3)	C19—C20—C15	120.1 (4)
N1—C9—H9	118.4	C19—C20—H20	119.9
C8—C9—H9	118.4	C15—C20—H20	119.9
N1—C10—C11	109.2 (2)	C9—N1—C10	119.9 (2)
N1—C10—H10A	109.8	C9—N1—Zn1	130.1 (2)
C11—C10—H10A	109.8	C10—N1—Zn1	109.86 (16)
N1—C10—H10B	109.8	C12—N2—C11	120.0 (2)
C11—C10—H10B	109.8	C12—N2—Zn1	130.7 (2)
H10A—C10—H10B	108.3	C11—N2—Zn1	109.00 (16)

C6—C1—C2—C3	−0.9 (5)	C16—C15—C20—C19	1.8 (5)
C7—C1—C2—C3	−179.6 (3)	C14—C15—C20—C19	−179.8 (3)
C1—C2—C3—C4	0.2 (7)	C8—C9—N1—C10	179.1 (3)
C2—C3—C4—C5	0.3 (7)	C8—C9—N1—Zn1	4.1 (4)
C3—C4—C5—C6	0.0 (7)	C11—C10—N1—C9	150.3 (3)
C4—C5—C6—C1	−0.8 (5)	C11—C10—N1—Zn1	−33.8 (3)
C2—C1—C6—C5	1.2 (5)	N2—Zn1—N1—C9	−176.0 (3)
C7—C1—C6—C5	179.8 (3)	Cl2—Zn1—N1—C9	71.1 (3)
C6—C1—C7—C8	9.5 (5)	Cl1—Zn1—N1—C9	−64.2 (3)
C2—C1—C7—C8	−171.8 (3)	N2—Zn1—N1—C10	8.69 (19)
C1—C7—C8—C9	−179.4 (3)	Cl2—Zn1—N1—C10	−104.23 (19)
C7—C8—C9—N1	−177.3 (3)	Cl1—Zn1—N1—C10	120.48 (19)
N1—C10—C11—N2	50.0 (3)	C13—C12—N2—C11	−176.8 (3)
N2—C12—C13—C14	179.6 (3)	C13—C12—N2—Zn1	−3.6 (4)
C12—C13—C14—C15	−177.5 (3)	C10—C11—N2—C12	132.9 (3)
C13—C14—C15—C16	−173.3 (3)	C10—C11—N2—Zn1	−41.7 (3)
C13—C14—C15—C20	8.3 (5)	N1—Zn1—N2—C12	−155.4 (3)
C20—C15—C16—C17	−1.8 (5)	Cl2—Zn1—N2—C12	−44.7 (3)
C14—C15—C16—C17	179.7 (3)	Cl1—Zn1—N2—C12	92.0 (3)
C15—C16—C17—C18	0.1 (6)	N1—Zn1—N2—C11	18.43 (19)
C16—C17—C18—C19	1.8 (7)	Cl2—Zn1—N2—C11	129.09 (17)
C17—C18—C19—C20	−1.9 (7)	Cl1—Zn1—N2—C11	−94.19 (18)
C18—C19—C20—C15	0.0 (6)

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₂₀H₂₀N₂)]
M_r	424.65
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	300
a, b, c (Å)	7.2140 (8), 20.265 (2), 14.0906 (16)
β (°)	94.913 (2)
V (Å³)	2052.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.46
Crystal size (mm)	0.23 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan SADABS (Sheldrick, 1996)
T_min, T_max	0.730, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	15814, 4458, 3027
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.132, 0.99
No. of reflections	4458
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.29

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank Dr Zhi-Dong Lin for assistance with the data.

References

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