Dichlorido[(S)-N-(1-phenyl­ethyl­idene)-1-(pyridin-2-yl)ethanamine-κ2N,N′]zinc(II) dichloro­methane solvate

Nayab, S.; Paek, S.-M.; Jeong, J.H.

doi:10.1107/S1600536810029387

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m1027

https://doi.org/10.1107/S1600536810029387

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Dichlorido[(S)-N-(1-phenylethylidene)-1-(pyridin-2-yl)ethanamine-κ²N,N′]zinc(II) dichloromethane solvate

Saira Nayab,^a Seung-Min Paek ^a and Jong Hwa Jeong ^a ^*

^aDepartment of Chemistry, Kyungpook National University, Taegu, 702-701, Republic of Korea
^*Correspondence e-mail: jeongjh@knu.ac.kr

(Received 5 July 2010; accepted 23 July 2010; online 31 July 2010)

In the title compound, [ZnCl₂(C₁₅H₁₆N₂)]·CH₂Cl₂, the Zn(II) atom has a distorted tetrahedral coordination by two Cl atoms and two N atoms from the organic ligand [the average Zn—N and Zn—Cl bond lengths are 2.060 (4) Å and Zn—Cl = 2.179 (16) Å, respectively]. The dihedral angle between the N—Zn—N and Cl—Zn—Cl planes is 89.9 (1)°. The phenyl ring forms a dihedral angle of 40.6 (5)° with the imine plane.

Related literature

For related structures see: Brunner & Fisch (1987 ); Nguyen & Jeong (2008 ).

Experimental

Crystal data

[ZnCl₂(C₁₅H₁₆N₂)]·CH₂Cl₂
M_r = 445.51
Triclinic, $[P \overline 1]$
a = 7.9381 (7) Å
b = 10.7187 (8) Å
c = 11.8426 (7) Å
α = 96.724 (6)°
β = 108.466 (6)°
γ = 97.968 (7)°
V = 932.53 (13) Å³
Z = 2
Mo Kα radiation
μ = 1.89 mm⁻¹
T = 295 K
0.45 × 0.40 × 0.35 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (ABSCALC; McArdle & Daly, 1999 ) T_min = 0.489, T_max = 0.569
3871 measured reflections
3463 independent reflections
2873 reflections with I > 2σ(I)
R_int = 0.009
3 standard reflections every 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.197
S = 1.11
3463 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −1.38 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD (McArdle, 1999 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810029387/rk2219sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029387/rk2219Isup2.hkl

checkCIF report

Comment top

The ligand, (S)–N–(1–phenylethylidene)–1–(pyridin–2–yl)ethanamine, was obtained from reaction of (S)–1–(pyridin–2–yl)ethanamine with acetophenone in toluene solution. The similar ligand was used in Rh or Zn complex (Brunner & Fisch, 1987; Nguyen & Jeong, 2008). The geometry around the Zn atom is nearly tetrahedral with two chlorine atoms and the one pyridyl and one amine nitrogen atoms of the ligand (Fig. 1). The dihedral angle between N—Zn—N and Cl—Zn—Cl planes is 89.9 (1)°. The phenyl cycle forms dihedral angle 40.6 (5)° with imine plane. This value may be explained by steric hinderance between the Cl atoms and phenyl moiety of organic ligand.

Related literature top

For related structures see: Brunner & Fisch (1987); Nguyen & Jeong (2008).

Experimental top

Acetophenone (2.04 g, 0.017 mol) was added to a solution of (S)–1–(pyridin–2–yl)ethanamine (2.07 g, 0.017 mol) in 40 ml of toluene. The reaction mixture was heated under reflux for 2 days in a Dean–Stark equipment. The solvent was removed by evaporation to yield pale brown oil, 3.43 g (90% yield). ¹H NMR (400 MHz, CDCl₃) δ 8.61 (t, 2H, ArH), 8.28 (d, 2H, ArH), 7.70 (m, 2H, ArH), 7.24 (m, 2H, ArH), 7.10 (m, 1H, ArH), 5.04 (q, J = 6.56 Hz, 1H, CH), 2.42 (s, 3H, CH₃), 1.44 (d, J = 6.56 Hz, 3H, CH₃). A solution of the ligand (1.01 g, 4.5 mmol) in ethanol (5 ml) was added dropwise to a solution of ZnCl₂ (0.61 g, 4.5 mmol) in ethanol (10 ml). The mixture was stirred overnight at room temperature. The solvent was removed to yield white solid product. Colourless crystals were obtained by slow difussion of hexane to CH₂Cl₂ solution (1.43 g, 80%). Anal. Cacld. For [C₁₅H₁₆Cl₂N₂Zn]^.CH₂Cl₂: C, 43.14%; H, 4.07%; N, 6.29%. Found: C, 43.04%; H, 4.12%, N, 6.19%. ¹H NMR (400 MHz, CDCl₃) δ 8.63 (t, 2H, ArH), 8.44 (d, 2H, ArH), 7.81 (m, 2H, ArH), 7.24 (m, 2H, ArH), 7.11 (m, 1H, ArH), 5.23 (m, 1H, CH), 2.56 (s, 3H, CH₃), 2.00 (d, J = 6.42 Hz, 3H, CH₃).

Structure description top

For related structures see: Brunner & Fisch (1987); Nguyen & Jeong (2008).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD (McArdle, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms are presented as a small spheres of arbitrary radius.

Dichlorido[(S)-N-(1-phenylethylidene)-1-(pyridin-2-yl) ethanamine-κ²N,N']zinc(II) dichloromehtane solvate top

Crystal data top

[ZnCl₂(C₁₅H₁₆N₂)]·CH₂Cl₂	Z = 2
M_r = 445.51	F(000) = 452
Triclinic, P1	D_x = 1.587 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9381 (7) Å	Cell parameters from 25 reflections
b = 10.7187 (8) Å	θ = 10–12°
c = 11.8426 (7) Å	µ = 1.89 mm⁻¹
α = 96.724 (6)°	T = 295 K
β = 108.466 (6)°	Block, colourless
γ = 97.968 (7)°	0.45 × 0.40 × 0.35 mm
V = 932.53 (13) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2873 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	R_int = 0.009
Graphite monochromator	θ_max = 25.5°, θ_min = 1.8°
ω/2θ–scans	h = 0→9
Absorption correction: ψ scan (ABSCALC; McArdle & Daly, 1999)	k = −12→12
T_min = 0.489, T_max = 0.569	l = −14→13
3871 measured reflections	3 standard reflections every 60 min
3463 independent reflections	intensity decay: none

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.197	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.124P)² + 1.3285P] where P = (F_o² + 2F_c²)/3
3463 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −1.38 e Å⁻³

Crystal data top

[ZnCl₂(C₁₅H₁₆N₂)]·CH₂Cl₂	γ = 97.968 (7)°
M_r = 445.51	V = 932.53 (13) Å³
Triclinic, P1	Z = 2
a = 7.9381 (7) Å	Mo Kα radiation
b = 10.7187 (8) Å	µ = 1.89 mm⁻¹
c = 11.8426 (7) Å	T = 295 K
α = 96.724 (6)°	0.45 × 0.40 × 0.35 mm
β = 108.466 (6)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2873 reflections with I > 2σ(I)
Absorption correction: ψ scan (ABSCALC; McArdle & Daly, 1999)	R_int = 0.009
T_min = 0.489, T_max = 0.569	3 standard reflections every 60 min
3871 measured reflections	intensity decay: none
3463 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.197	H-atom parameters constrained
S = 1.11	Δρ_max = 0.85 e Å⁻³
3463 reflections	Δρ_min = −1.38 e Å⁻³
210 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Zn	0.75251 (7)	0.65883 (5)	0.79296 (5)	0.0462 (2)
Cl1	0.57114 (18)	0.80013 (15)	0.78335 (15)	0.0610 (4)
Cl2	0.6555 (2)	0.45749 (14)	0.80264 (16)	0.0704 (5)
N1	0.8371 (6)	0.6589 (4)	0.6459 (4)	0.0460 (9)
N2	1.0239 (5)	0.7302 (4)	0.8835 (3)	0.0385 (8)
C1	0.7332 (8)	0.6417 (6)	0.5294 (5)	0.0572 (13)
H1	0.6083	0.6236	0.5100	0.069*
C2	0.8008 (9)	0.6494 (6)	0.4393 (5)	0.0631 (15)
H2	0.7244	0.6359	0.3594	0.076*
C3	0.9837 (10)	0.6773 (7)	0.4673 (6)	0.0697 (17)
H3	1.0336	0.6839	0.4065	0.084*
C4	1.0944 (8)	0.6959 (6)	0.5869 (5)	0.0578 (14)
H4	1.2195	0.7151	0.6077	0.069*
C5	1.0162 (7)	0.6852 (5)	0.6742 (4)	0.0428 (10)
C6	1.1306 (6)	0.6999 (5)	0.8060 (4)	0.0415 (10)
H6	1.2345	0.7695	0.8246	0.050*
C7	1.1975 (8)	0.5778 (6)	0.8317 (5)	0.0587 (14)
H7A	1.2645	0.5867	0.9163	0.088*
H7B	1.2744	0.5605	0.7857	0.088*
H7C	1.0963	0.5085	0.8094	0.088*
C8	1.1009 (6)	0.7966 (5)	0.9897 (4)	0.0410 (10)
C9	1.2985 (7)	0.8533 (6)	1.0420 (5)	0.0597 (14)
H9A	1.3577	0.8262	0.9868	0.090*
H9B	1.3503	0.8252	1.1174	0.090*
H9C	1.3141	0.9449	1.0554	0.090*
C10	0.9907 (6)	0.8173 (5)	1.0667 (4)	0.0406 (10)
C11	0.8521 (7)	0.7222 (5)	1.0654 (5)	0.0516 (12)
H11	0.8315	0.6425	1.0178	0.062*
C12	0.7449 (8)	0.7450 (7)	1.1340 (6)	0.0623 (15)
H12	0.6519	0.6805	1.1317	0.075*
C13	0.7731 (9)	0.8608 (7)	1.2053 (6)	0.0654 (16)
H13	0.6987	0.8753	1.2504	0.078*
C14	0.9100 (10)	0.9546 (6)	1.2103 (6)	0.0665 (16)
H14	0.9294	1.0331	1.2595	0.080*
C15	1.0214 (8)	0.9348 (6)	1.1429 (5)	0.0557 (13)
H15	1.1163	0.9993	1.1481	0.067*
Cl1S	0.4042 (8)	0.8397 (6)	0.3886 (5)	0.204 (2)
Cl2S	0.2730 (12)	1.0098 (6)	0.5042 (6)	0.243 (3)
C1S	0.368 (2)	0.9595 (16)	0.4503 (14)	0.168 (7)
H1S1	0.4877	0.9926	0.5093	0.201*
H1S2	0.3596	1.0119	0.3880	0.201*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.0334 (3)	0.0516 (4)	0.0525 (4)	0.0000 (2)	0.0164 (3)	0.0086 (3)
Cl1	0.0397 (7)	0.0689 (9)	0.0770 (9)	0.0123 (6)	0.0210 (6)	0.0166 (7)
Cl2	0.0694 (10)	0.0540 (8)	0.0794 (10)	−0.0110 (7)	0.0235 (8)	0.0106 (7)
N1	0.040 (2)	0.053 (2)	0.043 (2)	0.0033 (17)	0.0138 (17)	0.0084 (18)
N2	0.0327 (19)	0.044 (2)	0.0399 (19)	0.0044 (15)	0.0150 (16)	0.0062 (16)
C1	0.050 (3)	0.065 (3)	0.048 (3)	0.005 (2)	0.008 (2)	0.005 (2)
C2	0.070 (4)	0.072 (4)	0.040 (3)	0.007 (3)	0.011 (3)	0.006 (3)
C3	0.083 (4)	0.085 (4)	0.048 (3)	0.011 (3)	0.033 (3)	0.013 (3)
C4	0.054 (3)	0.073 (4)	0.050 (3)	0.008 (3)	0.026 (3)	0.007 (3)
C5	0.042 (2)	0.042 (2)	0.044 (2)	0.0045 (19)	0.015 (2)	0.0058 (19)
C6	0.033 (2)	0.051 (3)	0.043 (2)	0.0041 (19)	0.0182 (19)	0.006 (2)
C7	0.060 (3)	0.069 (4)	0.054 (3)	0.028 (3)	0.022 (3)	0.011 (3)
C8	0.040 (2)	0.042 (2)	0.041 (2)	0.0069 (19)	0.0132 (19)	0.0090 (19)
C9	0.041 (3)	0.074 (4)	0.055 (3)	0.002 (3)	0.013 (2)	−0.004 (3)
C10	0.040 (2)	0.046 (2)	0.038 (2)	0.0100 (19)	0.0141 (19)	0.0112 (19)
C11	0.051 (3)	0.055 (3)	0.051 (3)	0.004 (2)	0.020 (2)	0.014 (2)
C12	0.055 (3)	0.079 (4)	0.062 (3)	0.009 (3)	0.029 (3)	0.025 (3)
C13	0.074 (4)	0.084 (4)	0.060 (3)	0.034 (3)	0.040 (3)	0.025 (3)
C14	0.087 (5)	0.064 (4)	0.057 (3)	0.024 (3)	0.033 (3)	0.004 (3)
C15	0.062 (3)	0.053 (3)	0.051 (3)	0.008 (3)	0.022 (3)	0.004 (2)
Cl1S	0.228 (5)	0.247 (6)	0.205 (5)	0.112 (5)	0.120 (4)	0.085 (4)
Cl2S	0.366 (10)	0.203 (5)	0.186 (5)	0.083 (6)	0.120 (6)	0.022 (4)
C1S	0.155 (12)	0.176 (14)	0.126 (10)	0.047 (11)	0.004 (9)	−0.051 (10)

Geometric parameters (Å, º) top

Zn—N1	2.055 (4)	C7—H7C	0.9600
Zn—N2	2.065 (4)	C8—C10	1.469 (7)
Zn—Cl2	2.2175 (16)	C8—C9	1.499 (7)
Zn—Cl1	2.2182 (15)	C9—H9A	0.9600
N1—C5	1.333 (6)	C9—H9B	0.9600
N1—C1	1.340 (7)	C9—H9C	0.9600
N2—C8	1.282 (6)	C10—C11	1.388 (7)
N2—C6	1.471 (6)	C10—C15	1.403 (7)
C1—C2	1.343 (9)	C11—C12	1.375 (8)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.363 (10)	C12—C13	1.365 (9)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.384 (9)	C13—C14	1.355 (10)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.372 (7)	C14—C15	1.388 (8)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.513 (7)	C15—H15	0.9300
C6—C7	1.507 (8)	Cl1S—C1S	1.509 (14)
C6—H6	0.9800	Cl2S—C1S	1.268 (15)
C7—H7A	0.9600	C1S—H1S1	0.9700
C7—H7B	0.9600	C1S—H1S2	0.9700

N1—Zn—N2	81.55 (16)	C6—C7—H7C	109.5
N1—Zn—Cl2	107.97 (13)	H7A—C7—H7C	109.5
N2—Zn—Cl2	116.13 (12)	H7B—C7—H7C	109.5
N1—Zn—Cl1	107.49 (13)	N2—C8—C10	118.5 (4)
N2—Zn—Cl1	115.59 (12)	N2—C8—C9	124.1 (4)
Cl2—Zn—Cl1	120.09 (6)	C10—C8—C9	117.3 (4)
C5—N1—C1	118.7 (5)	C8—C9—H9A	109.5
C5—N1—Zn	114.0 (3)	C8—C9—H9B	109.5
C1—N1—Zn	127.2 (4)	H9A—C9—H9B	109.5
C8—N2—C6	120.5 (4)	C8—C9—H9C	109.5
C8—N2—Zn	129.0 (3)	H9A—C9—H9C	109.5
C6—N2—Zn	110.4 (3)	H9B—C9—H9C	109.5
N1—C1—C2	123.1 (6)	C11—C10—C15	118.0 (5)
N1—C1—H1	118.5	C11—C10—C8	121.2 (5)
C2—C1—H1	118.5	C15—C10—C8	120.8 (5)
C1—C2—C3	118.7 (5)	C12—C11—C10	120.5 (5)
C1—C2—H2	120.6	C12—C11—H11	119.8
C3—C2—H2	120.6	C10—C11—H11	119.8
C2—C3—C4	119.5 (6)	C13—C12—C11	121.0 (6)
C2—C3—H3	120.3	C13—C12—H12	119.5
C4—C3—H3	120.3	C11—C12—H12	119.5
C5—C4—C3	118.7 (6)	C14—C13—C12	119.8 (6)
C5—C4—H4	120.6	C14—C13—H13	120.1
C3—C4—H4	120.6	C12—C13—H13	120.1
N1—C5—C4	121.3 (5)	C13—C14—C15	120.8 (6)
N1—C5—C6	117.6 (4)	C13—C14—H14	119.6
C4—C5—C6	121.1 (5)	C15—C14—H14	119.6
N2—C6—C7	108.9 (4)	C14—C15—C10	119.9 (6)
N2—C6—C5	110.2 (4)	C14—C15—H15	120.1
C7—C6—C5	110.2 (4)	C10—C15—H15	120.1
N2—C6—H6	109.2	Cl2S—C1S—Cl1S	147.9 (16)
C7—C6—H6	109.2	Cl2S—C1S—H1S1	99.8
C5—C6—H6	109.2	Cl1S—C1S—H1S1	99.8
C6—C7—H7A	109.5	Cl2S—C1S—H1S2	99.8
C6—C7—H7B	109.5	Cl1S—C1S—H1S2	99.8
H7A—C7—H7B	109.5	H1S1—C1S—H1S2	104.1

N2—Zn—N1—C5	8.3 (3)	Zn—N2—C6—C7	−94.2 (4)
Cl2—Zn—N1—C5	−106.5 (3)	C8—N2—C6—C5	−150.7 (4)
Cl1—Zn—N1—C5	122.6 (3)	Zn—N2—C6—C5	26.8 (4)
N2—Zn—N1—C1	−168.3 (5)	N1—C5—C6—N2	−21.5 (6)
Cl2—Zn—N1—C1	76.9 (5)	C4—C5—C6—N2	159.9 (5)
Cl1—Zn—N1—C1	−54.0 (5)	N1—C5—C6—C7	98.6 (5)
N1—Zn—N2—C8	157.6 (4)	C4—C5—C6—C7	−79.9 (6)
Cl2—Zn—N2—C8	−96.5 (4)	C6—N2—C8—C10	−176.1 (4)
Cl1—Zn—N2—C8	52.2 (4)	Zn—N2—C8—C10	6.9 (7)
N1—Zn—N2—C6	−19.7 (3)	C6—N2—C8—C9	2.8 (7)
Cl2—Zn—N2—C6	86.2 (3)	Zn—N2—C8—C9	−174.2 (4)
Cl1—Zn—N2—C6	−125.1 (3)	N2—C8—C10—C11	36.8 (7)
C5—N1—C1—C2	0.2 (9)	C9—C8—C10—C11	−142.2 (5)
Zn—N1—C1—C2	176.7 (5)	N2—C8—C10—C15	−142.5 (5)
N1—C1—C2—C3	−0.8 (10)	C9—C8—C10—C15	38.5 (7)
C1—C2—C3—C4	0.6 (11)	C15—C10—C11—C12	2.2 (8)
C2—C3—C4—C5	0.1 (10)	C8—C10—C11—C12	−177.1 (5)
C1—N1—C5—C4	0.5 (8)	C10—C11—C12—C13	−0.5 (9)
Zn—N1—C5—C4	−176.4 (4)	C11—C12—C13—C14	−0.9 (9)
C1—N1—C5—C6	−178.0 (5)	C12—C13—C14—C15	0.5 (10)
Zn—N1—C5—C6	5.0 (6)	C13—C14—C15—C10	1.2 (9)
C3—C4—C5—N1	−0.7 (9)	C11—C10—C15—C14	−2.5 (8)
C3—C4—C5—C6	177.9 (5)	C8—C10—C15—C14	176.8 (5)
C8—N2—C6—C7	88.3 (5)

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₅H₁₆N₂)]·CH₂Cl₂
M_r	445.51
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.9381 (7), 10.7187 (8), 11.8426 (7)
α, β, γ (°)	96.724 (6), 108.466 (6), 97.968 (7)
V (Å³)	932.53 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.89
Crystal size (mm)	0.45 × 0.40 × 0.35

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (ABSCALC; McArdle & Daly, 1999)
T_min, T_max	0.489, 0.569
No. of measured, independent and observed [I > 2σ(I)] reflections	3871, 3463, 2873
R_int	0.009
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.197, 1.11
No. of reflections	3463
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −1.38

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD (McArdle, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Acknowledgements

This Research was supported by Kyungpook National University Research Fund, 2008.

References

Brunner, H. & Fisch, H. (1987). J. Organomet. Chem. 335, 1–14. CAS Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
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McArdle, P. & Daly, P. (1999). ABSCALC. National University of Ireland, Galway, Ireland. Google Scholar
Nguyen, Q. T. & Jeong, J. H. (2008). Acta Cryst. E64, m457. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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