[N-((E)-2-{[2-(Dimethyl­amino)­eth­yl]imino­meth­yl}phen­yl)-N-(2,6-dimethyl­phen­yl)anilinido-κ3N,N′,N′′]ethyl­zinc

Issa-Madongo, M.; Mu, Y.

doi:10.1107/S1600536811005514

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page m364

doi:10.1107/S1600536811005514

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[N-((E)-2-{[2-(Dimethylamino)ethyl]iminomethyl}phenyl)-N-(2,6-dimethylphenyl)anilinido-κ³N,N′,N′′]ethylzinc

Mathurin Issa-Madongo ^a ^* and Ying Mu ^a ^*

^aState Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, People's Republic of China
^*Correspondence e-mail: gw@jlu.edu.cn, ymu@jlu.edu.cn

(Received 26 January 2011; accepted 15 February 2011; online 23 February 2011)

The title ethyl–zinc complex, [Zn(C₂H₅)(C₁₉H₂₄N₃)], bears a tridentate anilinide–aldimine ligand and features one long Zn—N(amine) bond length, attributable to the crowded environment of the coordinated metal, arising from the dimethylphenyl group. The Zn^II ion adopts a distorted tetrahedral geometry, the dihedral angle between the two benzene rings being 86.05 (16)°.

Related literature

For the synthesis, luminescent properties and applications in catalysis of complexes bearing anilido–aldimine ligands, see: Liu et al. (2005 , 2006 ); Ren et al. (2007 ); Su et al. (2007 ); Yao et al. (2008 ).

Experimental

Crystal data

[Zn(C₂H₅)(C₁₉H₂₄N₃)]
M_r = 388.84
Monoclinic, P 2₁ /c
a = 7.3664 (15) Å
b = 13.849 (3) Å
c = 20.296 (4) Å
β = 99.26 (3)°
V = 2043.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 293 K
0.23 × 0.21 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.768, T_max = 0.803
18874 measured reflections
4571 independent reflections
2619 reflections with I > 2σ(I)
R_int = 0.116

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.189
S = 0.96
4571 reflections
231 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—C20	1.991 (5)
Zn1—N1	2.009 (3)
Zn1—N2	2.487 (4)
Zn1—N3	2.004 (4)

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005514/bh2336sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005514/bh2336Isup2.hkl

checkCIF report

Comment top

Complexes bearing chelating anilido-aldimine ligands have recently attracted attention because such ligands have similar framework and combine the steric and electronic characteristics of β-diketiminate and salicyaldiminato ligands, which have been extensively researched in coordination chemistry and catalysis. We have recently reported the luminescent properties of a series of Al(III) (Liu et al., 2005, 2006), Zn^II (Su et al., 2007) and B(III) (Ren et al., 2007) complexes with chelating anilido-aldimine ligands, and catalytic properties of Al(III) complexes (Yao et al., 2008) for the polymerization of ε-caprolactone. Good results have been obtained. As a part of our study, the preparation and crystal structure of the title ethyl zinc complex bearing N,N',N''-tridentate anilido-aldimine ligand is reported.

In the complex (Fig. 1), the C7═N1 [1.292 (6) Å] bond length is comparable to those found in similar anilido-imine compounds (Su et al., 2007). The bond distances Zn—N1 [2.009 (3) Å] and Zn—N3 [2.004 (4) Å] are similar to those in other anilido-aldimine zinc complexes. The pendant arm bond length Zn—N2 [2.487 (4) Å], in contrast, is longer than equivalent bonds found in other N,N',O-tridentate Schiff base Zn complexes. This may be due to the crowded environment in the metal center arising from the aryl group bonded to N3. The dihedral angle between the central benzene ring (C1···C6) and the benzene ring (C12···C17) is 86.05 (16)°.

Related literature top

For the synthesis, luminescent properties and applications in catalysis of complexes bearing anilido–aldimine ligands, see: Liu et al. (2005, 2006); Ren et al. (2007); Su et al. (2007); Yao et al. (2008).

Experimental top

The complex was synthesized according to the literature method (Su et al., 2007). A solution of ZnEt₂ (1.0 mol/L, 2.0 mmol) was added to a solution of the ligand (0.59 g, 2.0 mmol) in toluene (30 ml) at 273 K. After stirring for 24 h, the solution was evaporated to dryness and the resulting yellow powder was washed with hexane (Yield: 0.65 g, 90%). Anal. Calcd. for C₂₁H₂₉N₃Zn (388.87): C 64.86, H 7.52, N 10.81%; Found: C 64.62, H 7.44, N 10.65%.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the title complex, with displacement ellipsoids drawn at the 30% probability level.

[N-((E)-2-{[2-(Dimethylamino)ethyl]iminomethyl}phenyl)- N-(2,6-dimethylphenyl)anilinido- κ³N,N',N'']ethylzinc top

Crystal data top

[Zn(C₂H₅)(C₁₉H₂₄N₃)]	F(000) = 824
M_r = 388.84	D_x = 1.264 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10491 reflections
a = 7.3664 (15) Å	θ = 6.2–54.9°
b = 13.849 (3) Å	µ = 1.21 mm⁻¹
c = 20.296 (4) Å	T = 293 K
β = 99.26 (3)°	Block, yellow
V = 2043.5 (7) Å³	0.23 × 0.21 × 0.19 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4571 independent reflections
Radiation source: fine-focus sealed tube	2619 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.116
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
T_min = 0.768, T_max = 0.803	k = −16→17
18874 measured reflections	l = −24→26

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.097P)²] where P = (F_o² + 2F_c²)/3
4571 reflections	(Δ/σ)_max = 0.023
231 parameters	Δρ_max = 0.98 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³
0 constraints

Crystal data top

[Zn(C₂H₅)(C₁₉H₂₄N₃)]	V = 2043.5 (7) Å³
M_r = 388.84	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3664 (15) Å	µ = 1.21 mm⁻¹
b = 13.849 (3) Å	T = 293 K
c = 20.296 (4) Å	0.23 × 0.21 × 0.19 mm
β = 99.26 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4571 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2619 reflections with I > 2σ(I)
T_min = 0.768, T_max = 0.803	R_int = 0.116
18874 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 0.96	Δρ_max = 0.98 e Å⁻³
4571 reflections	Δρ_min = −0.63 e Å⁻³
231 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7787 (7)	0.8763 (3)	0.8847 (2)	0.0497 (10)
C2	0.7141 (7)	0.8858 (3)	0.8154 (2)	0.0558 (11)
H2	0.7400	0.8373	0.7866	0.067*
C3	0.6141 (8)	0.9649 (4)	0.7893 (3)	0.0672 (14)
H3	0.5740	0.9683	0.7435	0.081*
C4	0.5719 (8)	1.0393 (4)	0.8297 (3)	0.0671 (14)
H4	0.5068	1.0931	0.8115	0.080*
C5	0.6275 (7)	1.0321 (3)	0.8964 (3)	0.0580 (12)
H5	0.5944	1.0808	0.9237	0.070*
C6	0.7337 (6)	0.9537 (3)	0.9266 (2)	0.0483 (10)
C7	0.7748 (7)	0.9542 (3)	0.9974 (2)	0.0512 (11)
H7	0.7175	1.0017	1.0190	0.061*
C8	0.8819 (8)	0.8962 (3)	1.1069 (2)	0.0581 (12)
H8A	0.8122	0.9508	1.1194	0.070*
H8B	1.0066	0.9005	1.1310	0.070*
C9	0.7926 (8)	0.8012 (3)	1.1237 (2)	0.0594 (12)
H9A	0.7967	0.7965	1.1716	0.071*
H9B	0.6646	0.8003	1.1027	0.071*
C10	0.7658 (10)	0.6345 (4)	1.0890 (3)	0.090 (2)
H10A	0.8310	0.5805	1.0745	0.135*
H10B	0.6627	0.6499	1.0554	0.135*
H10C	0.7229	0.6183	1.1299	0.135*
C11	1.0496 (9)	0.6923 (4)	1.1502 (3)	0.0737 (16)
H11A	1.0089	0.6737	1.1910	0.111*
H11B	1.1306	0.7468	1.1584	0.111*
H11C	1.1138	0.6393	1.1339	0.111*
C12	0.9206 (7)	0.7257 (3)	0.8645 (2)	0.0505 (10)
C13	0.8071 (8)	0.6443 (3)	0.8554 (2)	0.0580 (12)
C14	0.8532 (8)	0.5707 (3)	0.8151 (2)	0.0662 (14)
H14	0.7762	0.5174	0.8068	0.079*
C15	1.0110 (9)	0.5750 (3)	0.7871 (3)	0.0701 (16)
H15	1.0435	0.5233	0.7621	0.084*
C16	1.1190 (9)	0.6548 (4)	0.7958 (2)	0.0667 (14)
H16	1.2234	0.6577	0.7755	0.080*
C17	1.0774 (8)	0.7330 (3)	0.8347 (2)	0.0579 (12)
C18	1.1964 (9)	0.8214 (4)	0.8426 (3)	0.0718 (15)
H18A	1.1236	0.8770	0.8275	0.108*
H18B	1.2934	0.8144	0.8165	0.108*
H18C	1.2486	0.8294	0.8887	0.108*
C19	0.6367 (9)	0.6368 (4)	0.8876 (3)	0.0818 (17)
H19A	0.5704	0.5792	0.8724	0.123*
H19B	0.5598	0.6921	0.8758	0.123*
H19C	0.6714	0.6342	0.9353	0.123*
C20	1.2613 (7)	0.7185 (3)	1.0170 (3)	0.0611 (12)
H20A	1.3406	0.7502	0.9898	0.073*
H20B	1.3175	0.7252	1.0634	0.073*
C21	1.2474 (9)	0.6109 (3)	0.9989 (3)	0.0777 (16)
H21A	1.1714	0.5788	1.0263	0.117*
H21B	1.3680	0.5827	1.0062	0.117*
H21C	1.1941	0.6038	0.9528	0.117*
N1	0.8827 (6)	0.8962 (2)	1.03518 (17)	0.0499 (9)
N2	0.8894 (6)	0.7183 (2)	1.10019 (19)	0.0564 (10)
N3	0.8810 (6)	0.8002 (2)	0.91016 (18)	0.0520 (9)
Zn1	1.01743 (8)	0.78379 (3)	1.00320 (2)	0.0531 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.040 (3)	0.051 (2)	0.058 (3)	0.0013 (17)	0.007 (2)	0.0038 (17)
C2	0.052 (3)	0.063 (2)	0.053 (3)	0.007 (2)	0.010 (2)	0.0040 (19)
C3	0.055 (4)	0.080 (3)	0.066 (3)	0.017 (3)	0.008 (3)	0.021 (2)
C4	0.052 (4)	0.068 (3)	0.083 (4)	0.021 (2)	0.018 (3)	0.023 (2)
C5	0.045 (3)	0.052 (2)	0.079 (3)	0.0110 (19)	0.015 (2)	0.009 (2)
C6	0.039 (3)	0.043 (2)	0.064 (3)	0.0028 (16)	0.011 (2)	0.0048 (17)
C7	0.046 (3)	0.043 (2)	0.066 (3)	0.0022 (17)	0.012 (2)	−0.0009 (18)
C8	0.060 (4)	0.059 (3)	0.055 (3)	0.003 (2)	0.008 (2)	−0.0090 (19)
C9	0.060 (4)	0.064 (3)	0.056 (3)	0.006 (2)	0.015 (2)	0.002 (2)
C10	0.100 (6)	0.065 (3)	0.106 (5)	−0.013 (3)	0.016 (4)	−0.008 (3)
C11	0.076 (5)	0.084 (3)	0.058 (3)	0.022 (3)	−0.001 (3)	0.006 (2)
C12	0.051 (3)	0.050 (2)	0.048 (2)	0.0102 (18)	0.002 (2)	0.0017 (17)
C13	0.057 (4)	0.057 (2)	0.056 (3)	0.010 (2)	−0.001 (2)	0.0015 (19)
C14	0.067 (4)	0.055 (3)	0.069 (3)	0.003 (2)	−0.011 (3)	−0.003 (2)
C15	0.093 (5)	0.055 (3)	0.059 (3)	0.020 (3)	0.002 (3)	−0.010 (2)
C16	0.074 (4)	0.072 (3)	0.056 (3)	0.025 (3)	0.015 (3)	0.002 (2)
C17	0.064 (4)	0.058 (3)	0.050 (3)	0.010 (2)	0.004 (2)	0.0031 (18)
C18	0.065 (4)	0.073 (3)	0.078 (4)	−0.002 (3)	0.016 (3)	0.000 (2)
C19	0.065 (5)	0.081 (3)	0.096 (4)	−0.004 (3)	0.003 (3)	−0.001 (3)
C20	0.051 (3)	0.069 (3)	0.061 (3)	0.014 (2)	0.002 (2)	−0.004 (2)
C21	0.073 (5)	0.066 (3)	0.089 (4)	0.018 (3)	−0.001 (3)	−0.003 (2)
N1	0.050 (3)	0.0491 (18)	0.050 (2)	0.0020 (15)	0.0082 (17)	−0.0017 (14)
N2	0.056 (3)	0.056 (2)	0.056 (2)	0.0045 (17)	0.0019 (19)	−0.0002 (16)
N3	0.055 (3)	0.0526 (18)	0.047 (2)	0.0103 (16)	0.0023 (17)	−0.0017 (14)
Zn1	0.0500 (4)	0.0525 (3)	0.0541 (3)	0.0111 (2)	0.0003 (2)	−0.0051 (2)

Geometric parameters (Å, º) top

C1—N3	1.349 (5)	C12—C17	1.391 (7)
C1—C2	1.417 (6)	C12—C13	1.398 (7)
C1—C6	1.441 (6)	C12—N3	1.447 (5)
C2—C3	1.376 (6)	C13—C14	1.383 (6)
C2—H2	0.9300	C13—C19	1.510 (8)
C3—C4	1.384 (8)	C14—C15	1.375 (8)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.353 (7)	C15—C16	1.356 (8)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.418 (6)	C16—C17	1.404 (6)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.419 (6)	C17—C18	1.499 (7)
C7—N1	1.292 (6)	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—N1	1.457 (5)	C18—H18C	0.9600
C8—C9	1.533 (6)	C19—H19A	0.9600
C8—H8A	0.9700	C19—H19B	0.9600
C8—H8B	0.9700	C19—H19C	0.9600
C9—N2	1.471 (6)	C20—C21	1.534 (6)
C9—H9A	0.9700	Zn1—C20	1.991 (5)
C9—H9B	0.9700	C20—H20A	0.9700
C10—N2	1.470 (7)	C20—H20B	0.9700
C10—H10A	0.9600	C21—H21A	0.9600
C10—H10B	0.9600	C21—H21B	0.9600
C10—H10C	0.9600	C21—H21C	0.9600
C11—N2	1.472 (7)	Zn1—N1	2.009 (3)
C11—H11A	0.9600	Zn1—N2	2.487 (4)
C11—H11B	0.9600	Zn1—N3	2.004 (4)
C11—H11C	0.9600

N3—C1—C2	122.1 (4)	C13—C14—H14	119.4
N3—C1—C6	121.5 (4)	C16—C15—C14	119.9 (4)
C2—C1—C6	116.4 (4)	C16—C15—H15	120.0
C3—C2—C1	122.0 (4)	C14—C15—H15	120.0
C3—C2—H2	119.0	C15—C16—C17	121.7 (5)
C1—C2—H2	119.0	C15—C16—H16	119.1
C2—C3—C4	121.5 (5)	C17—C16—H16	119.1
C2—C3—H3	119.3	C12—C17—C16	117.4 (5)
C4—C3—H3	119.3	C12—C17—C18	121.7 (4)
C5—C4—C3	118.5 (4)	C16—C17—C18	120.9 (5)
C5—C4—H4	120.8	C17—C18—H18A	109.5
C3—C4—H4	120.8	C17—C18—H18B	109.5
C4—C5—C6	123.1 (4)	H18A—C18—H18B	109.5
C4—C5—H5	118.5	C17—C18—H18C	109.5
C6—C5—H5	118.5	H18A—C18—H18C	109.5
C5—C6—C7	116.6 (4)	H18B—C18—H18C	109.5
C5—C6—C1	118.6 (4)	C13—C19—H19A	109.5
C7—C6—C1	124.7 (4)	C13—C19—H19B	109.5
N1—C7—C6	127.6 (4)	H19A—C19—H19B	109.5
N1—C7—H7	116.2	C13—C19—H19C	109.5
C6—C7—H7	116.2	H19A—C19—H19C	109.5
N1—C8—C9	107.1 (4)	H19B—C19—H19C	109.5
N1—C8—H8A	110.3	C21—C20—Zn1	112.5 (4)
C9—C8—H8A	110.3	C21—C20—H20A	109.1
N1—C8—H8B	110.3	Zn1—C20—H20A	109.1
C9—C8—H8B	110.3	C21—C20—H20B	109.1
H8A—C8—H8B	108.6	Zn1—C20—H20B	109.1
N2—C9—C8	110.5 (4)	H20A—C20—H20B	107.8
N2—C9—H9A	109.6	C20—C21—H21A	109.5
C8—C9—H9A	109.6	C20—C21—H21B	109.5
N2—C9—H9B	109.6	H21A—C21—H21B	109.5
C8—C9—H9B	109.6	C20—C21—H21C	109.5
H9A—C9—H9B	108.1	H21A—C21—H21C	109.5
N2—C10—H10A	109.5	H21B—C21—H21C	109.5
N2—C10—H10B	109.5	C7—N1—C8	119.6 (4)
H10A—C10—H10B	109.5	C7—N1—Zn1	125.3 (3)
N2—C10—H10C	109.5	C8—N1—Zn1	113.8 (3)
H10A—C10—H10C	109.5	C10—N2—C9	110.2 (4)
H10B—C10—H10C	109.5	C10—N2—C11	108.7 (4)
N2—C11—H11A	109.5	C9—N2—C11	110.1 (4)
N2—C11—H11B	109.5	C10—N2—Zn1	118.1 (3)
H11A—C11—H11B	109.5	C9—N2—Zn1	103.7 (2)
N2—C11—H11C	109.5	C11—N2—Zn1	105.7 (3)
H11A—C11—H11C	109.5	C1—N3—C12	118.0 (4)
H11B—C11—H11C	109.5	C1—N3—Zn1	127.9 (3)
C17—C12—C13	121.4 (4)	C12—N3—Zn1	113.6 (3)
C17—C12—N3	119.6 (4)	C20—Zn1—N3	119.23 (18)
C13—C12—N3	118.8 (4)	C20—Zn1—N1	142.01 (18)
C14—C13—C12	118.3 (5)	N3—Zn1—N1	91.01 (14)
C14—C13—C19	120.3 (5)	C20—Zn1—N2	99.88 (18)
C12—C13—C19	121.3 (4)	N3—Zn1—N2	126.21 (16)
C15—C14—C13	121.1 (5)	N1—Zn1—N2	75.94 (13)
C15—C14—H14	119.4

Experimental details

Crystal data
Chemical formula	[Zn(C₂H₅)(C₁₉H₂₄N₃)]
M_r	388.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.3664 (15), 13.849 (3), 20.296 (4)
β (°)	99.26 (3)
V (Å³)	2043.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.23 × 0.21 × 0.19

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.768, 0.803
No. of measured, independent and observed [I > 2σ(I)] reflections	18874, 4571, 2619
R_int	0.116
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.189, 0.96
No. of reflections	4571
No. of parameters	231
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.63

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—C20	1.991 (5)	Zn1—N2	2.487 (4)
Zn1—N1	2.009 (3)	Zn1—N3	2.004 (4)

Acknowledgements

We thank the National Natural Science Foundation of China (grant Nos. 20772044 and 20674024). IMM is also grateful for support from Jilin University.

References

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