Dichlorido{(E)-2,4,6-trimethyl-N-[phen­yl(2-pyridyl)methyl­idene]aniline-κ2N,N′}palladium(II)

Yang, C.-H.; Peng, Y.-L.; Wang, M.-H.; Shih, K.-C.; Hsueh, M.-L.

doi:10.1107/S1600536810016466

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page m633

https://doi.org/10.1107/S1600536810016466

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Dichlorido{(E)-2,4,6-trimethyl-N-[phenyl(2-pyridyl)methylidene]aniline-κ²N,N′}palladium(II)

Cheng-Hsien Yang,^a Ya-Liu Peng,^b Mei-Hua Wang,^a Kuo-Chen Shih ^a and Mao-Lin Hsueh ^a ^*

^aNano-Powder & Thin Film Technology Center, ITRI South, Tainan 709, Taiwan, Republic of China, and ^bDepartment of Chemistry, National Chung Hsing University, Taichung 402, Taiwan, Republic of China
^*Correspondence e-mail: mmhsueh@itri.org.tw

(Received 14 April 2010; accepted 5 May 2010; online 8 May 2010)

The title complex, [PdCl₂(C₂₁H₂₀N₂)], contains a Pd^II atom in a slightly distorted square-planar coordination environment defined by two N atoms from one 2,4,6-trimethyl-N-[phenyl(2-pyridyl)methylidene]aniline ligand and two Cl atoms, forming a five-membered ring (N—Pd—N—C—C).

Related literature

For the synthesis of pyridyl-imine ligands, see: Meneghetti et al. (1999 ). For the design and synthesis of metal-organic frameworks, see: Lai et al. (2005 ); Pelagattia et al. (2005 ); Zhang et al. (2008 ). For related structures, see: Hsueh et al. (2006 ); Zhang et al. (2008). For the application of the title compound in Suzuki–Miyaura reactions, see: Li (2003 ); Miyaura & Suzuki (1995 ); Na et al. (2004 ); Nicolaou et al. (2005 ); Rajagopal et al. (2002 ); Tomioka et al. (2004 ).

Experimental

Crystal data

[PdCl₂(C₂₁H₂₀N₂)]
M_r = 477.69
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.4807 (6) Å
b = 15.1483 (13) Å
c = 17.7147 (15) Å
V = 2007.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.20 mm⁻¹
T = 298 K
0.35 × 0.33 × 0.22 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.738, T_max = 1.000
11233 measured reflections
3956 independent reflections
3871 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.052
S = 1.01
3956 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.52 e Å⁻³
Absolute structure: Flack (1983 ), 1670 Friedel pairs
Flack parameter: 0.02 (2)

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810016466/pk2244sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016466/pk2244Isup2.hkl

checkCIF report

Comment top

Recently, palladium-catalyzed Suzuki-Miyaura reactions involving cross-coupling of aryl halides with aryl boronic acids have emerged as the most important synthetic methods for the preparation of biaryl compounds (Miyaura et al., 1995; Na et al., 2004; Rajagopal et al., 2002; Li 2003; Tomioka et al., 2004; Nicolaou et al., 2005). Thus, because of its utility as an important synthetic methodology, a significant amount of research focus had been devoted to designing improved catalysts for the Suzuki-Miyaura cross-coupling reaction. It is noteworthy that there has been a continuing interest in the further development of more efficient and selective catalytic systems for the synthesis of biaryls. However, only a few examples of N,N' pyridyl-imine palladium complexes have been reported as catalysts in coupling reaction (Lai et al., 2005; Pelagattia et al., 2005). Herein, we report the synthesis and crystal structure of the title palladium (II) complex that is certainly a potential catalyst in cross-coupling reactions.

The structure of the title compound is a mononuclear configuration with the metal center bound to two N atoms (one from the imine group and one from the pyridine ring) and two Cl atoms (Fig. 1). The coordination geometry around Pd^II atom is slightly distorted square planar, and the distances of Pd(1)—N(1) and Pd(1)—N(2) are 2.025 (2) and 2.033 (2) Å, respectively. It is noticed that the trans angles (N2—Pd—Cl1 and N1—Pd—Cl2) in the PdN₂Cl₂ core do not deviate more than 8° from the ideal value of 180°. Moreover, the planes of the pyridine (N1—C1—C2—C3—C4—C5) and phenyl rings (C8—C9—C10—C11—C12 and C13—C14—C15—C16—C17—C18) are close to perpendicular, and the dihedral angles between them are 80.9 (3) and 82.8 (3)°, respectively. All bond distances and bond angles lie within normal ranges, which are essentially similar to the pyridyl-imine palladium (II) complex (Hsueh et al., 2006; Zhang et al., 2008).

Related literature top

For the synthesis of pyridyl-imine ligands, see: Meneghetti et al. (1999). For the design and synthesis of metal-organic frameworks, see: Lai et al. (2005); Pelagattia et al. (2005); Zhang et al. (2008). For related structures, see: Hsueh et al. (2006); Zhang et al. (2008). For the application of the title compound in Suzuki–Miyaura reactions, see: Li (2003); Miyaura & Suzuki (1995); Na et al. (2004); Nicolaou et al. (2005); Rajagopal et al. (2002); Tomioka et al. (2004).

Experimental top

The title compound was prepared by the reaction of palladium(II) dichloride (17.733 mg, 0.1 mmol) with (E)-2,4,6-trimethyl-N-(phenyl(pyridin-2-yl)methylene)aniline (30.016 mg, 0.1 mmol) in EtOH (20 ml). The mixture was stirred at room temperature for 24 h. The mixture turned yellow immediately. After removal of solvents, dichloromethane (20 ml) was added and the solution was filtered through Celite. The filtrate was slowly evaporated at room temperature to yield yellow crystals suitable for X-ray analysis. Yield: 41.084 mg (86%). Analysis calculated for C₂₁H₂₀Cl₂N₂Pd: C 52.80, H 4.22, N 5.86%; found: C 52.65, H 4.17, N 5.93%.

Structure description top

For the synthesis of pyridyl-imine ligands, see: Meneghetti et al. (1999). For the design and synthesis of metal-organic frameworks, see: Lai et al. (2005); Pelagattia et al. (2005); Zhang et al. (2008). For related structures, see: Hsueh et al. (2006); Zhang et al. (2008). For the application of the title compound in Suzuki–Miyaura reactions, see: Li (2003); Miyaura & Suzuki (1995); Na et al. (2004); Nicolaou et al. (2005); Rajagopal et al. (2002); Tomioka et al. (2004).

Computing details top

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecular structure of the title compound with displacement ellipsoids shown at the 30% probability level.

Dichlorido{(E)-2,4,6-trimethyl-N-[phenyl(2- pyridyl)methylidene]aniline-κ²N,N'}palladium(II) top

Crystal data top

[PdCl₂(C₂₁H₂₀N₂)]	F(000) = 960
M_r = 477.69	D_x = 1.581 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4812 reflections
a = 7.4807 (6) Å	θ = 2.9–2.6°
b = 15.1483 (13) Å	µ = 1.20 mm⁻¹
c = 17.7147 (15) Å	T = 298 K
V = 2007.4 (3) Å³	Parallelpiped, yellow
Z = 4	0.35 × 0.33 × 0.22 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3956 independent reflections
Radiation source: fine-focus sealed tube	3871 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 26.1°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
T_min = 0.738, T_max = 1.000	k = −16→18
11233 measured reflections	l = −21→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.019	H-atom parameters constrained
wR(F²) = 0.052	w = 1/[σ²(F_o²) + (0.040P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.002
3956 reflections	Δρ_max = 0.20 e Å⁻³
238 parameters	Δρ_min = −0.52 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1670 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (2)

Crystal data top

[PdCl₂(C₂₁H₂₀N₂)]	V = 2007.4 (3) Å³
M_r = 477.69	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.4807 (6) Å	µ = 1.20 mm⁻¹
b = 15.1483 (13) Å	T = 298 K
c = 17.7147 (15) Å	0.35 × 0.33 × 0.22 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3956 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3871 reflections with I > 2σ(I)
T_min = 0.738, T_max = 1.000	R_int = 0.024
11233 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	H-atom parameters constrained
wR(F²) = 0.052	Δρ_max = 0.20 e Å⁻³
S = 1.01	Δρ_min = −0.52 e Å⁻³
3956 reflections	Absolute structure: Flack (1983), 1670 Friedel pairs
238 parameters	Absolute structure parameter: 0.02 (2)
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Pd1	0.262038 (18)	0.612368 (9)	0.476057 (8)	0.02890 (6)
Cl1	0.41648 (8)	0.68412 (4)	0.56891 (3)	0.04639 (14)
Cl2	0.19993 (9)	0.49999 (4)	0.55734 (3)	0.04722 (15)
N1	0.3065 (2)	0.70552 (11)	0.39625 (10)	0.0321 (4)
N2	0.1064 (2)	0.56451 (11)	0.39132 (10)	0.0308 (3)
C1	0.4227 (3)	0.77241 (15)	0.39906 (14)	0.0424 (5)
H1A	0.4974	0.7776	0.4408	0.051*
C2	0.4354 (4)	0.83417 (17)	0.34181 (16)	0.0527 (6)
H2A	0.5191	0.8794	0.3446	0.063*
C3	0.3231 (4)	0.82774 (16)	0.28102 (14)	0.0498 (6)
H3A	0.3274	0.8696	0.2426	0.060*
C4	0.2022 (3)	0.75775 (15)	0.27725 (13)	0.0418 (5)
H4A	0.1258	0.7518	0.2362	0.050*
C5	0.1982 (3)	0.69758 (13)	0.33577 (11)	0.0314 (4)
C6	0.0837 (3)	0.61804 (13)	0.33544 (11)	0.0302 (4)
C7	−0.0452 (3)	0.60379 (14)	0.27275 (12)	0.0344 (4)
C8	−0.2010 (4)	0.65290 (18)	0.27039 (14)	0.0493 (6)
H8A	−0.2234	0.6950	0.3074	0.059*
C9	−0.3241 (4)	0.6395 (2)	0.21285 (17)	0.0622 (8)
H9A	−0.4306	0.6712	0.2123	0.075*
C10	−0.2883 (4)	0.5791 (2)	0.15659 (15)	0.0594 (7)
H10A	−0.3704	0.5701	0.1179	0.071*
C11	−0.1303 (5)	0.5321 (2)	0.15769 (16)	0.0674 (8)
H11A	−0.1052	0.4924	0.1191	0.081*
C12	−0.0104 (4)	0.54350 (19)	0.21532 (15)	0.0526 (7)
H12A	0.0948	0.5108	0.2161	0.063*
C13	0.0126 (3)	0.48204 (13)	0.39711 (12)	0.0316 (4)
C14	−0.1580 (3)	0.48020 (14)	0.42893 (12)	0.0364 (5)
C15	−0.2372 (3)	0.39752 (15)	0.43887 (13)	0.0451 (5)
H15A	−0.3513	0.3946	0.4596	0.054*
C16	−0.1526 (4)	0.32013 (15)	0.41912 (13)	0.0513 (7)
C17	0.0171 (4)	0.32429 (15)	0.38896 (14)	0.0469 (6)
H17A	0.0757	0.2723	0.3761	0.056*
C18	0.1027 (3)	0.40533 (14)	0.37726 (13)	0.0392 (5)
C19	−0.2509 (4)	0.56211 (18)	0.45550 (16)	0.0563 (6)
H19A	−0.3451	0.5464	0.4897	0.084*
H19B	−0.3004	0.5928	0.4129	0.084*
H19C	−0.1667	0.5997	0.4808	0.084*
C20	−0.2428 (7)	0.23101 (19)	0.43118 (19)	0.0839 (11)
H20A	−0.3672	0.2399	0.4421	0.126*
H20B	−0.1871	0.2011	0.4727	0.126*
H20C	−0.2310	0.1959	0.3863	0.126*
C21	0.2913 (4)	0.40809 (18)	0.34700 (18)	0.0607 (7)
H21A	0.3515	0.4592	0.3664	0.091*
H21B	0.2882	0.4109	0.2929	0.091*
H21C	0.3541	0.3559	0.3625	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.02800 (8)	0.02850 (8)	0.03020 (9)	0.00077 (6)	−0.00266 (6)	−0.00482 (5)
Cl1	0.0497 (3)	0.0470 (3)	0.0424 (3)	−0.0033 (2)	−0.0130 (3)	−0.0131 (2)
Cl2	0.0583 (4)	0.0409 (3)	0.0424 (3)	−0.0035 (2)	−0.0076 (3)	0.0079 (2)
N1	0.0311 (9)	0.0286 (8)	0.0366 (9)	−0.0025 (7)	0.0017 (7)	−0.0065 (7)
N2	0.0283 (8)	0.0309 (8)	0.0331 (9)	−0.0014 (7)	0.0009 (7)	−0.0058 (7)
C1	0.0406 (12)	0.0392 (12)	0.0472 (13)	−0.0095 (10)	−0.0008 (11)	−0.0067 (10)
C2	0.0574 (16)	0.0424 (13)	0.0583 (15)	−0.0211 (12)	0.0032 (13)	−0.0013 (12)
C3	0.0617 (16)	0.0399 (13)	0.0478 (13)	−0.0088 (12)	0.0065 (12)	0.0057 (11)
C4	0.0473 (14)	0.0419 (12)	0.0360 (11)	−0.0059 (10)	−0.0007 (10)	0.0045 (9)
C5	0.0307 (10)	0.0310 (10)	0.0325 (10)	−0.0008 (8)	0.0022 (8)	−0.0056 (8)
C6	0.0313 (10)	0.0280 (9)	0.0313 (10)	0.0004 (9)	0.0013 (8)	−0.0044 (8)
C7	0.0379 (11)	0.0348 (10)	0.0306 (10)	−0.0073 (9)	−0.0021 (8)	−0.0017 (8)
C8	0.0466 (15)	0.0562 (14)	0.0450 (13)	0.0096 (12)	−0.0083 (11)	−0.0094 (11)
C9	0.0431 (14)	0.079 (2)	0.0646 (18)	0.0041 (13)	−0.0127 (13)	0.0015 (15)
C10	0.0598 (18)	0.0728 (18)	0.0457 (14)	−0.0164 (14)	−0.0216 (13)	−0.0035 (13)
C11	0.076 (2)	0.082 (2)	0.0443 (15)	−0.0021 (17)	−0.0119 (15)	−0.0287 (15)
C12	0.0534 (15)	0.0607 (16)	0.0439 (14)	0.0069 (12)	−0.0049 (11)	−0.0176 (12)
C13	0.0360 (11)	0.0277 (10)	0.0309 (10)	−0.0030 (8)	−0.0043 (8)	−0.0030 (8)
C14	0.0372 (11)	0.0379 (11)	0.0342 (11)	−0.0042 (9)	−0.0007 (9)	−0.0016 (9)
C15	0.0440 (12)	0.0521 (13)	0.0392 (11)	−0.0149 (12)	−0.0013 (10)	0.0018 (9)
C16	0.081 (2)	0.0354 (12)	0.0378 (12)	−0.0186 (12)	−0.0085 (12)	0.0033 (10)
C17	0.0682 (17)	0.0292 (11)	0.0433 (13)	−0.0007 (11)	−0.0094 (12)	−0.0043 (10)
C18	0.0442 (12)	0.0351 (11)	0.0383 (12)	0.0021 (9)	−0.0060 (9)	−0.0054 (9)
C19	0.0447 (13)	0.0544 (14)	0.0696 (15)	0.0053 (12)	0.0157 (13)	−0.0040 (12)
C20	0.130 (3)	0.0479 (15)	0.0738 (19)	−0.040 (2)	0.011 (3)	0.0052 (14)
C21	0.0497 (15)	0.0511 (15)	0.0814 (19)	0.0127 (12)	0.0105 (14)	−0.0107 (14)

Geometric parameters (Å, º) top

Pd1—N1	2.0250 (18)	C10—H10A	0.9300
Pd1—N2	2.0334 (17)	C11—C12	1.370 (4)
Pd1—Cl2	2.2776 (6)	C11—H11A	0.9300
Pd1—Cl1	2.2851 (5)	C12—H12A	0.9300
N1—C1	1.336 (3)	C13—C18	1.389 (3)
N1—C5	1.348 (3)	C13—C14	1.396 (3)
N2—C6	1.291 (3)	C14—C15	1.397 (3)
N2—C13	1.436 (3)	C14—C19	1.498 (3)
C1—C2	1.383 (4)	C15—C16	1.377 (4)
C1—H1A	0.9300	C15—H15A	0.9300
C2—C3	1.369 (4)	C16—C17	1.378 (4)
C2—H2A	0.9300	C16—C20	1.525 (3)
C3—C4	1.395 (3)	C17—C18	1.400 (3)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.381 (3)	C18—C21	1.509 (4)
C4—H4A	0.9300	C19—H19A	0.9600
C5—C6	1.479 (3)	C19—H19B	0.9600
C6—C7	1.486 (3)	C19—H19C	0.9600
C7—C8	1.384 (3)	C20—H20A	0.9600
C7—C12	1.392 (3)	C20—H20B	0.9600
C8—C9	1.389 (4)	C20—H20C	0.9600
C8—H8A	0.9300	C21—H21A	0.9600
C9—C10	1.379 (4)	C21—H21B	0.9600
C9—H9A	0.9300	C21—H21C	0.9600
C10—C11	1.380 (5)

N1—Pd1—N2	80.04 (7)	C10—C11—C12	120.4 (3)
N1—Pd1—Cl2	174.72 (5)	C10—C11—H11A	119.8
N2—Pd1—Cl2	94.79 (5)	C12—C11—H11A	119.8
N1—Pd1—Cl1	95.05 (5)	C11—C12—C7	120.3 (3)
N2—Pd1—Cl1	172.09 (5)	C11—C12—H12A	119.8
Cl2—Pd1—Cl1	90.21 (2)	C7—C12—H12A	119.8
C1—N1—C5	119.2 (2)	C18—C13—C14	122.0 (2)
C1—N1—Pd1	127.55 (16)	C18—C13—N2	118.19 (19)
C5—N1—Pd1	113.20 (13)	C14—C13—N2	119.53 (18)
C6—N2—C13	122.46 (17)	C15—C14—C13	117.2 (2)
C6—N2—Pd1	114.68 (13)	C15—C14—C19	120.4 (2)
C13—N2—Pd1	122.48 (13)	C13—C14—C19	122.3 (2)
N1—C1—C2	122.0 (2)	C16—C15—C14	122.4 (2)
N1—C1—H1A	119.0	C16—C15—H15A	118.8
C2—C1—H1A	119.0	C14—C15—H15A	118.8
C3—C2—C1	119.1 (2)	C15—C16—C17	118.9 (2)
C3—C2—H2A	120.5	C15—C16—C20	121.0 (3)
C1—C2—H2A	120.5	C17—C16—C20	120.2 (3)
C2—C3—C4	119.3 (2)	C18—C17—C16	121.3 (2)
C2—C3—H3A	120.3	C18—C17—H17A	119.4
C4—C3—H3A	120.3	C16—C17—H17A	119.4
C5—C4—C3	118.7 (2)	C13—C18—C17	118.3 (2)
C5—C4—H4A	120.7	C13—C18—C21	121.4 (2)
C3—C4—H4A	120.7	C17—C18—C21	120.3 (2)
N1—C5—C4	121.65 (19)	C14—C19—H19A	109.5
N1—C5—C6	115.08 (18)	C14—C19—H19B	109.5
C4—C5—C6	123.19 (19)	H19A—C19—H19B	109.5
N2—C6—C5	115.63 (17)	C14—C19—H19C	109.5
N2—C6—C7	124.55 (18)	H19A—C19—H19C	109.5
C5—C6—C7	119.82 (17)	H19B—C19—H19C	109.5
C8—C7—C12	119.2 (2)	C16—C20—H20A	109.5
C8—C7—C6	119.40 (19)	C16—C20—H20B	109.5
C12—C7—C6	121.3 (2)	H20A—C20—H20B	109.5
C7—C8—C9	120.1 (2)	C16—C20—H20C	109.5
C7—C8—H8A	119.9	H20A—C20—H20C	109.5
C9—C8—H8A	119.9	H20B—C20—H20C	109.5
C8—C9—C10	119.9 (3)	C18—C21—H21A	109.5
C8—C9—H9A	120.0	C18—C21—H21B	109.5
C10—C9—H9A	120.0	H21A—C21—H21B	109.5
C11—C10—C9	119.9 (2)	C18—C21—H21C	109.5
C11—C10—H10A	120.0	H21A—C21—H21C	109.5
C9—C10—H10A	120.0	H21B—C21—H21C	109.5

Experimental details

Crystal data
Chemical formula	[PdCl₂(C₂₁H₂₀N₂)]
M_r	477.69
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.4807 (6), 15.1483 (13), 17.7147 (15)
V (Å³)	2007.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.20
Crystal size (mm)	0.35 × 0.33 × 0.22

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.738, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11233, 3956, 3871
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.052, 1.01
No. of reflections	3956
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.52
Absolute structure	Flack (1983), 1670 Friedel pairs
Absolute structure parameter	0.02 (2)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

Financial support from the Ministry of Economic Affairs, Taiwan, is appreciated.

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