Chloridocyclo­hexyl[(1,2,5,6-η)-cyclo­octa-1,5-diene]platinum(II)

Ha, K.

doi:10.1107/S1600536809050910

metal-organic compounds

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Volume 65| Part 12| December 2009| Page m1707

doi:10.1107/S1600536809050910

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Chloridocyclohexyl[(1,2,5,6-η)-cycloocta-1,5-diene]platinum(II)

Kwang Ha ^a ^*

^aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

(Received 25 November 2009; accepted 26 November 2009; online 28 November 2009)

In the title complex, [Pt(C₆H₁₁)Cl(C₈H₁₂)], the Pt^II ion lies in a distorted square-planar environment defined by the Cl and cyclohexyl C atoms and the mid-points of the two π-coordinated double bonds of cycloocta-1,5-diene. As a result of the different trans influences of the Cl atom and the cyclohexyl group, the Pt—C bonds trans to the cyclohexyl group are longer than those trans to the Cl atom.

Related literature

For the crystal structure of [(cod)PtCl₂] (cod = cycloocta-1,5-diene), see: Goel et al. (1982 ); Syed et al. (1984 ). For the crystal structures of [(cod)Pt(CH₃)L] (L = OH, CH₃ or Cl), see: Klein et al. (1999 ).

Experimental

Crystal data

[Pt(C₆H₁₁)Cl(C₈H₁₂)]
M_r = 421.86
Monoclinic, P 2₁ /n
a = 10.6505 (5) Å
b = 12.3514 (6) Å
c = 11.1609 (6) Å
β = 105.175 (1)°
V = 1417.01 (12) Å³
Z = 4
Mo Kα radiation
μ = 10.06 mm⁻¹
T = 296 K
0.20 × 0.16 × 0.15 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.122, T_max = 0.221
10108 measured reflections
3481 independent reflections
2343 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.083
S = 1.12
3481 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 1.12 e Å⁻³
Δρ_min = −1.79 e Å⁻³

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050910/ng2696sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050910/ng2696Isup2.hkl

checkCIF report

Comment top

In the title complex, [Pt(C₆H₁₁)Cl(C₈H₁₂)], the central Pt^II ion lies in a distorted square-planar environment defined by the Cl and cyclohexyl C atoms and the two mid-points (M1, M2) of the π-coordinated double bonds of cycloocta-1,5-diene (cod) ligand (M1 and M2 denote the mid-points of the olefinic bonds C1—C2 and C5—C6, respectively) (Fig. 1 and Fig. 2). The Pt, Cl, C9 atoms and the mid-points lie in a coordination plane with the largest deviation of 0.021 Å (C9) from the least-squares plane, and with bond angles in the range of 85.2°–92.2°. Because of the different trans influences of the Cl atom and the cyclohexyl group, the Pt—C bonds trans to C9 of the cyclohexyl group are on average 0.215 Å longer than those trans to the Cl atom (Pt1—C1/C2 = 2.316 (7) and 2.337 (8) Å, Pt1—C5/C6 = 2.111 (8) and 2.112 (8) Å). The distances between the Pt atom and the mid-points are 2.228 Å (M1) and 1.992 Å (M2). The cod ligand coordinates to the Pt atom in the twist-boat conformation with the coordinated double-bond lengths of 1.339 (11) and 1.402 (12) Å, and the cod ring angles lie in the range of 113.0 (8)°–127.1 (8)°. The σ-bonded cyclohexyl ring is in the chair conformation with the ring angles of 109.9 (8)°–112.0 (8)°.

Related literature top

For the crystal structure of [(cod)PtCl₂] (cod = cycloocta-1,5-diene), see: Goel et al. (1982); Syed et al. (1984). For the crystal structures of [(cod)Pt(CH₃)L] (L = OH, CH₃ or Cl), see: Klein et al. (1999).

Experimental top

To a suspension of [(cod)PtCl₂] (0.5015 g, 1.34 mmol) in ether (30 ml) was added cyclohexylmagnesium chloride (2.0 M solution in ether, 4.1 ml, 8.04 mmol) and stirred for 24 h at -5 °C. After methanolysis with 1 ml MeOH, the resulting mixture was diluted with ether (20 ml), and then filtered directly through a plug of Al₂O₃ (3 cm x 2 cm) and eluted with ether (80 ml). The solvent was removed under vacuum and the residue was dried, to give a white powder (0.3655 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from an ethyl acetate solution.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, with displacement ellipsoids drawn at the 30% probability level for non-H atoms.
	Fig. 2. View of the unit-cell contents of the title compound.

Chloridocyclohexyl[(1,2,5,6-η)-cycloocta-1,5-diene]platinum(II) top

Crystal data top

[Pt(C₆H₁₁)Cl(C₈H₁₂)]	F(000) = 808
M_r = 421.86	D_x = 1.977 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3669 reflections
a = 10.6505 (5) Å	θ = 2.4–27.8°
b = 12.3514 (6) Å	µ = 10.06 mm⁻¹
c = 11.1609 (6) Å	T = 296 K
β = 105.175 (1)°	Block, colorless
V = 1417.01 (12) Å³	0.20 × 0.16 × 0.15 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	3481 independent reflections
Radiation source: fine-focus sealed tube	2343 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→14
T_min = 0.122, T_max = 0.221	k = −8→16
10108 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) = 0.083	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0112P)² + 4.7457P] where P = (F_o² + 2F_c²)/3
3481 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 1.12 e Å⁻³
0 restraints	Δρ_min = −1.79 e Å⁻³

Crystal data top

[Pt(C₆H₁₁)Cl(C₈H₁₂)]	V = 1417.01 (12) Å³
M_r = 421.86	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.6505 (5) Å	µ = 10.06 mm⁻¹
b = 12.3514 (6) Å	T = 296 K
c = 11.1609 (6) Å	0.20 × 0.16 × 0.15 mm
β = 105.175 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3481 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2343 reflections with I > 2σ(I)
T_min = 0.122, T_max = 0.221	R_int = 0.050
10108 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.12	Δρ_max = 1.12 e Å⁻³
3481 reflections	Δρ_min = −1.79 e Å⁻³
145 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
Pt1	0.23435 (3)	0.38659 (3)	0.59178 (3)	0.03388 (11)
Cl1	0.0531 (2)	0.2747 (2)	0.5501 (2)	0.0491 (6)
C1	0.1992 (9)	0.4337 (7)	0.7812 (7)	0.043 (2)
H1	0.1372	0.3870	0.8078	0.051*
C2	0.1440 (8)	0.5121 (8)	0.7019 (8)	0.044 (2)
H2	0.0487	0.5132	0.6801	0.052*
C3	0.2067 (9)	0.6204 (8)	0.6984 (8)	0.053 (2)
H3A	0.2625	0.6364	0.7802	0.064*
H3B	0.1396	0.6755	0.6785	0.064*
C4	0.2864 (10)	0.6255 (8)	0.6048 (9)	0.063 (3)
H4A	0.2299	0.6477	0.5256	0.076*
H4B	0.3522	0.6812	0.6308	0.076*
C5	0.3523 (8)	0.5229 (7)	0.5861 (8)	0.043 (2)
H5	0.3865	0.5243	0.5128	0.052*
C6	0.4195 (8)	0.4513 (8)	0.6782 (9)	0.052 (3)
H6	0.4921	0.4135	0.6578	0.062*
C7	0.4382 (10)	0.4719 (9)	0.8158 (9)	0.068 (3)
H7A	0.5169	0.4351	0.8607	0.082*
H7B	0.4522	0.5489	0.8307	0.082*
C8	0.3306 (11)	0.4376 (9)	0.8696 (8)	0.065 (3)
H8A	0.3276	0.4870	0.9364	0.078*
H8B	0.3510	0.3663	0.9058	0.078*
C9	0.3060 (8)	0.3085 (8)	0.4561 (8)	0.044 (2)
H9	0.3882	0.3438	0.4554	0.053*
C10	0.2166 (11)	0.3210 (9)	0.3290 (8)	0.064 (3)
H10A	0.2023	0.3974	0.3099	0.076*
H10B	0.1332	0.2883	0.3267	0.076*
C11	0.2741 (13)	0.2672 (11)	0.2310 (10)	0.087 (4)
H11A	0.2116	0.2718	0.1504	0.105*
H11B	0.3517	0.3060	0.2262	0.105*
C12	0.3075 (11)	0.1516 (9)	0.2608 (10)	0.071 (3)
H12A	0.3513	0.1227	0.2017	0.085*
H12B	0.2282	0.1105	0.2530	0.085*
C13	0.3945 (10)	0.1387 (9)	0.3909 (9)	0.067 (3)
H13A	0.4785	0.1713	0.3952	0.080*
H13B	0.4083	0.0622	0.4096	0.080*
C14	0.3359 (9)	0.1916 (8)	0.4883 (8)	0.051 (2)
H14A	0.2567	0.1540	0.4911	0.061*
H14B	0.3968	0.1863	0.5696	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.03384 (17)	0.03547 (19)	0.03338 (16)	−0.00364 (17)	0.01065 (11)	−0.00381 (18)
Cl1	0.0403 (12)	0.0527 (15)	0.0538 (13)	−0.0132 (10)	0.0116 (10)	−0.0063 (12)
C1	0.070 (6)	0.037 (5)	0.028 (4)	0.006 (5)	0.025 (4)	−0.004 (4)
C2	0.042 (5)	0.048 (6)	0.043 (5)	0.007 (4)	0.015 (4)	−0.006 (5)
C3	0.056 (6)	0.054 (7)	0.048 (5)	0.012 (5)	0.010 (4)	0.002 (5)
C4	0.075 (7)	0.046 (7)	0.072 (7)	−0.006 (5)	0.026 (6)	−0.009 (6)
C5	0.049 (5)	0.044 (6)	0.049 (5)	−0.020 (4)	0.031 (4)	−0.019 (5)
C6	0.030 (5)	0.053 (6)	0.068 (6)	−0.015 (4)	0.005 (4)	−0.018 (6)
C7	0.062 (7)	0.067 (8)	0.058 (6)	0.000 (6)	−0.014 (5)	−0.007 (6)
C8	0.096 (9)	0.055 (7)	0.035 (5)	0.017 (6)	0.000 (5)	−0.006 (5)
C9	0.049 (5)	0.047 (6)	0.042 (5)	−0.008 (4)	0.022 (4)	−0.018 (4)
C10	0.096 (8)	0.056 (7)	0.046 (6)	0.018 (6)	0.033 (6)	0.007 (5)
C11	0.121 (11)	0.108 (12)	0.047 (6)	0.015 (9)	0.046 (7)	−0.009 (7)
C12	0.084 (8)	0.061 (8)	0.080 (8)	0.000 (6)	0.042 (7)	−0.024 (7)
C13	0.072 (7)	0.064 (8)	0.072 (7)	0.010 (6)	0.032 (6)	−0.012 (6)
C14	0.056 (6)	0.045 (6)	0.057 (6)	0.008 (5)	0.026 (5)	−0.013 (5)

Geometric parameters (Å, º) top

Pt1—C9	2.100 (8)	C7—H7A	0.9700
Pt1—C5	2.111 (8)	C7—H7B	0.9700
Pt1—C6	2.112 (8)	C8—H8A	0.9700
Pt1—C1	2.316 (7)	C8—H8B	0.9700
Pt1—Cl1	2.320 (2)	C9—C10	1.495 (12)
Pt1—C2	2.337 (8)	C9—C14	1.502 (12)
C1—C2	1.339 (11)	C9—H9	0.9800
C1—C8	1.487 (13)	C10—C11	1.538 (12)
C1—H1	0.9800	C10—H10A	0.9700
C2—C3	1.500 (13)	C10—H10B	0.9700
C2—H2	0.9800	C11—C12	1.488 (15)
C3—C4	1.510 (12)	C11—H11A	0.9700
C3—H3A	0.9700	C11—H11B	0.9700
C3—H3B	0.9700	C12—C13	1.513 (14)
C4—C5	1.490 (13)	C12—H12A	0.9700
C4—H4A	0.9700	C12—H12B	0.9700
C4—H4B	0.9700	C13—C14	1.534 (11)
C5—C6	1.402 (12)	C13—H13A	0.9700
C5—H5	0.9800	C13—H13B	0.9700
C6—C7	1.517 (12)	C14—H14A	0.9700
C6—H6	0.9800	C14—H14B	0.9700
C7—C8	1.487 (14)

C9—Pt1—C5	90.8 (3)	Pt1—C6—H6	114.4
C9—Pt1—C6	91.8 (4)	C8—C7—C6	116.8 (8)
C5—Pt1—C6	38.8 (3)	C8—C7—H7A	108.1
C9—Pt1—C1	161.8 (3)	C6—C7—H7A	108.1
C5—Pt1—C1	93.8 (3)	C8—C7—H7B	108.1
C6—Pt1—C1	80.9 (4)	C6—C7—H7B	108.1
C9—Pt1—Cl1	91.3 (2)	H7A—C7—H7B	107.3
C5—Pt1—Cl1	159.9 (3)	C7—C8—C1	115.6 (8)
C6—Pt1—Cl1	160.9 (3)	C7—C8—H8A	108.4
C1—Pt1—Cl1	90.5 (2)	C1—C8—H8A	108.4
C9—Pt1—C2	164.0 (3)	C7—C8—H8B	108.4
C5—Pt1—C2	79.5 (3)	C1—C8—H8B	108.4
C6—Pt1—C2	88.4 (4)	H8A—C8—H8B	107.4
C1—Pt1—C2	33.5 (3)	C10—C9—C14	111.7 (8)
Cl1—Pt1—C2	93.7 (2)	C10—C9—Pt1	112.0 (6)
C2—C1—C8	126.1 (9)	C14—C9—Pt1	111.3 (6)
C2—C1—Pt1	74.1 (5)	C10—C9—H9	107.2
C8—C1—Pt1	105.4 (6)	C14—C9—H9	107.2
C2—C1—H1	114.3	Pt1—C9—H9	107.2
C8—C1—H1	114.3	C9—C10—C11	110.9 (9)
Pt1—C1—H1	114.3	C9—C10—H10A	109.5
C1—C2—C3	122.7 (8)	C11—C10—H10A	109.5
C1—C2—Pt1	72.4 (5)	C9—C10—H10B	109.5
C3—C2—Pt1	109.3 (6)	C11—C10—H10B	109.5
C1—C2—H2	114.9	H10A—C10—H10B	108.0
C3—C2—H2	114.9	C12—C11—C10	111.9 (9)
Pt1—C2—H2	114.9	C12—C11—H11A	109.2
C2—C3—C4	113.0 (8)	C10—C11—H11A	109.2
C2—C3—H3A	109.0	C12—C11—H11B	109.2
C4—C3—H3A	109.0	C10—C11—H11B	109.2
C2—C3—H3B	109.0	H11A—C11—H11B	107.9
C4—C3—H3B	109.0	C11—C12—C13	111.5 (10)
H3A—C3—H3B	107.8	C11—C12—H12A	109.3
C5—C4—C3	115.5 (9)	C13—C12—H12A	109.3
C5—C4—H4A	108.4	C11—C12—H12B	109.3
C3—C4—H4A	108.4	C13—C12—H12B	109.3
C5—C4—H4B	108.4	H12A—C12—H12B	108.0
C3—C4—H4B	108.4	C12—C13—C14	112.0 (8)
H4A—C4—H4B	107.5	C12—C13—H13A	109.2
C6—C5—C4	127.1 (8)	C14—C13—H13A	109.2
C6—C5—Pt1	70.7 (5)	C12—C13—H13B	109.2
C4—C5—Pt1	111.6 (6)	C14—C13—H13B	109.2
C6—C5—H5	113.2	H13A—C13—H13B	107.9
C4—C5—H5	113.2	C9—C14—C13	109.9 (8)
Pt1—C5—H5	113.2	C9—C14—H14A	109.7
C5—C6—C7	122.9 (9)	C13—C14—H14A	109.7
C5—C6—Pt1	70.6 (5)	C9—C14—H14B	109.7
C7—C6—Pt1	112.7 (6)	C13—C14—H14B	109.7
C5—C6—H6	114.4	H14A—C14—H14B	108.2
C7—C6—H6	114.4

C9—Pt1—C1—C2	168.5 (9)	C9—Pt1—C6—C5	89.0 (6)
C5—Pt1—C1—C2	64.3 (6)	C1—Pt1—C6—C5	−107.8 (5)
C6—Pt1—C1—C2	101.0 (6)	Cl1—Pt1—C6—C5	−171.9 (6)
Cl1—Pt1—C1—C2	−96.1 (6)	C2—Pt1—C6—C5	−75.0 (5)
C9—Pt1—C1—C8	44.6 (14)	C9—Pt1—C6—C7	−152.5 (8)
C5—Pt1—C1—C8	−59.5 (7)	C5—Pt1—C6—C7	118.5 (10)
C6—Pt1—C1—C8	−22.8 (7)	C1—Pt1—C6—C7	10.6 (7)
Cl1—Pt1—C1—C8	140.1 (6)	Cl1—Pt1—C6—C7	−53.4 (13)
C2—Pt1—C1—C8	−123.8 (9)	C2—Pt1—C6—C7	43.4 (8)
C8—C1—C2—C3	−4.3 (14)	C5—C6—C7—C8	84.8 (12)
Pt1—C1—C2—C3	−102.0 (8)	Pt1—C6—C7—C8	4.0 (12)
C8—C1—C2—Pt1	97.7 (9)	C6—C7—C8—C1	−26.2 (14)
C9—Pt1—C2—C1	−166.9 (10)	C2—C1—C8—C7	−49.3 (13)
C5—Pt1—C2—C1	−113.8 (6)	Pt1—C1—C8—C7	32.0 (10)
C6—Pt1—C2—C1	−75.9 (6)	C5—Pt1—C9—C10	−97.5 (7)
Cl1—Pt1—C2—C1	85.2 (6)	C6—Pt1—C9—C10	−136.2 (7)
C9—Pt1—C2—C3	−47.6 (15)	C1—Pt1—C9—C10	157.9 (9)
C5—Pt1—C2—C3	5.4 (6)	Cl1—Pt1—C9—C10	62.6 (7)
C6—Pt1—C2—C3	43.4 (6)	C2—Pt1—C9—C10	−45.7 (15)
C1—Pt1—C2—C3	119.3 (9)	C5—Pt1—C9—C14	136.7 (7)
Cl1—Pt1—C2—C3	−155.5 (6)	C6—Pt1—C9—C14	98.0 (7)
C1—C2—C3—C4	93.5 (10)	C1—Pt1—C9—C14	32.1 (14)
Pt1—C2—C3—C4	12.5 (9)	Cl1—Pt1—C9—C14	−63.2 (6)
C2—C3—C4—C5	−33.3 (12)	C2—Pt1—C9—C14	−171.5 (10)
C3—C4—C5—C6	−43.5 (13)	C14—C9—C10—C11	−56.8 (11)
C3—C4—C5—Pt1	38.1 (10)	Pt1—C9—C10—C11	177.6 (7)
C9—Pt1—C5—C6	−91.9 (6)	C9—C10—C11—C12	54.8 (14)
C1—Pt1—C5—C6	70.4 (6)	C10—C11—C12—C13	−53.3 (14)
Cl1—Pt1—C5—C6	172.3 (6)	C11—C12—C13—C14	54.1 (13)
C2—Pt1—C5—C6	100.8 (6)	C10—C9—C14—C13	56.9 (10)
C9—Pt1—C5—C4	144.8 (7)	Pt1—C9—C14—C13	−177.1 (6)
C6—Pt1—C5—C4	−123.2 (9)	C12—C13—C14—C9	−55.3 (12)
C1—Pt1—C5—C4	−52.8 (7)	C1—C2—C5—C6	−7.2 (7)
Cl1—Pt1—C5—C4	49.1 (11)	C3—C4—C7—C8	22.4 (8)
C2—Pt1—C5—C4	−22.5 (7)	C3—C2—C1—C8	−4.3 (14)
C4—C5—C6—C7	−2.0 (14)	C4—C5—C6—C7	−2.0 (14)
Pt1—C5—C6—C7	−105.0 (9)	C2—C3—C4—C5	−33.3 (12)
C4—C5—C6—Pt1	103.0 (9)	C6—C7—C8—C1	−26.2 (14)

Experimental details

Crystal data
Chemical formula	[Pt(C₆H₁₁)Cl(C₈H₁₂)]
M_r	421.86
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.6505 (5), 12.3514 (6), 11.1609 (6)
β (°)	105.175 (1)
V (Å³)	1417.01 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.06
Crystal size (mm)	0.20 × 0.16 × 0.15

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.122, 0.221
No. of measured, independent and observed [I > 2σ(I)] reflections	10108, 3481, 2343
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.083, 1.12
No. of reflections	3481
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.12, −1.79

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Acknowledgements

This work was supported by a Korea Research Foundation grant funded by the Korean Government (MOEHRD) (KRF-2007–412-J02001).

References

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