cis-1,2-Bis{[4-(4-pyrid­yl)pyrimidin-2-yl]sulfanylmeth­yl}benzene

Dong, H.-Z.; Zhu, H.-B.; Gou, S.-H.

doi:10.1107/S1600536809045450

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o2977

doi:10.1107/S1600536809045450

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cis-1,2-Bis{[4-(4-pyridyl)pyrimidin-2-yl]sulfanylmethyl}benzene

Hua-Ze Dong,^a ^* Hai-Bin Zhu ^b and Shao-Hua Gou ^b

^aDeparment of Chemistry and Chemical Engineering, Hefei Normal University, Hefei 230061, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: dapdong@163.com

(Received 25 October 2009; accepted 29 October 2009; online 4 November 2009)

The molecular skeleton of the title molecule, C₂₆H₂₀N₆S₂, adopts a cis conformation with the two arms positioned on one side of the benzene ring plane. Intramolecular π–π interactions between the pyrimidine rings [centroid–centroid distance = 3.654 (2) Å] and between the pyridine rings [centroid–centroid distance = 3.775 (2) Å] help to set the molecular conformation; the pyrimidine rings, as well as the pyridine rings, are nearly parallel, forming dihedral angles of 4.12 (14) and 2.46 (14)°, respectively.

Related literature

For related compounds, see: Dong et al. (2008 , 2009 ); Huang et al. (2007 ).

Experimental

Crystal data

C₂₆H₂₀N₆S₂
M_r = 480.62
Monoclinic, P 2₁ /n
a = 8.6078 (11) Å
b = 27.102 (3) Å
c = 10.0282 (12) Å
β = 103.661 (2)°
V = 2273.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 291 K
0.32 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.917, T_max = 0.966
13064 measured reflections
4903 independent reflections
3067 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.108
S = 0.90
4903 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045450/cv2646sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045450/cv2646Isup2.hkl

checkCIF report

Comment top

Remarkable attention has been paid to the rational design and assembly of new coordination polymers with heterocyclic thiolates or thioethers in recent years. In our previous work, we reported aserials dithioether ligands (Dong et al., 2008; 2009; Huang et al., 2007). As our continuing study, herein we report the molecular structure of the title compound - the newly synthesized ligand derived from 4-(4-pyridinyl)pyrimidine-2-thiol.

The molecular structure of the title compound is shown in Fig. 1. The molecule adopts a cis conformation with two arms positioned on one side of the benzene ring plane. It is noted that intramolecular π-π interactions between the pyrimidinyl rings [centroid-centroid distance of 3.654 (2) Å] and between the pyridinyl rings [centroid-centroid distance of 3.775 (2) Å] set the molecular conformation - the pyrimidinyl rings, as well as the pyridinyl ones, are nearly parallel forming dihedral angles of 4.12 (14)° and 2.46 (14)°, respectively.

Related literature top

For related compounds, see: Dong et al. (2008, 2009); Huang et al. (2007).

Experimental top

All solvents and chemicals were of analytical grade and were used without further purification. The title compound was prepared by similar procedure reported in the literature (Dong et al., 2008; 2009), To a solution of 4-(4-pyridinyl)pyrimidine-2-thiol (3.78 g, 20 mmol) and sodium hydroxide (0.80 g, 20 mmol) in dry ethanol (300 ml), 1,2-bis(bromomethyl)benzene (2.64 g, 10 mmol) in CCl₄ (30 ml) was added. The mixture was stirred and refluxed for 8 h. After cooling, precipitates were filtered, washed in water and ethanol, and dried in vacuum. Anal. Calcd for C₂₆H₂₀N₆S₂: C, 64.98; H, 4.19; N, 17.49%. Found: C, 65.07; H, 4.52; N, 17.34%. Single crystals of ligang suitable for X-ray diffraction were grown from methanol solution by slow evaporation in air at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

cis-1,2-Bis{[4-(4-pyridyl)pyrimidin-2-yl]sulfanylmethyl}benzene top

Crystal data top

C₂₆H₂₀N₆S₂	F(000) = 1000.0
M_r = 480.62	D_x = 1.404 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4903 reflections
a = 8.6078 (11) Å	θ = 2.2–27.0°
b = 27.102 (3) Å	µ = 0.26 mm⁻¹
c = 10.0282 (12) Å	T = 291 K
β = 103.661 (2)°	Block, pale yellow
V = 2273.3 (5) Å³	0.32 × 0.18 × 0.16 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4903 independent reflections
Radiation source: fine-focus sealed tube	3067 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→8
T_min = 0.917, T_max = 0.966	k = −34→31
13064 measured reflections	l = −12→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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0421P)²] where P = (F_o² + 2F_c²)/3
4903 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₆H₂₀N₆S₂	V = 2273.3 (5) Å³
M_r = 480.62	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.6078 (11) Å	µ = 0.26 mm⁻¹
b = 27.102 (3) Å	T = 291 K
c = 10.0282 (12) Å	0.32 × 0.18 × 0.16 mm
β = 103.661 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4903 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3067 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.966	R_int = 0.052
13064 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 0.90	Δρ_max = 0.32 e Å⁻³
4903 reflections	Δρ_min = −0.22 e Å⁻³
307 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
C1	0.7345 (3)	0.22381 (8)	0.8229 (2)	0.0384 (5)
C2	0.9748 (3)	0.25202 (9)	0.9324 (2)	0.0494 (6)
H2	1.0799	0.2469	0.9807	0.059*
C3	0.9230 (3)	0.29935 (8)	0.9059 (2)	0.0474 (6)
H3	0.9909	0.3259	0.9351	0.057*
C4	0.7668 (3)	0.30680 (8)	0.8343 (2)	0.0411 (6)
C5	0.6967 (3)	0.35654 (8)	0.8048 (2)	0.0436 (6)
C6	0.7521 (3)	0.39620 (9)	0.8867 (3)	0.0623 (8)
H6	0.8355	0.3922	0.9640	0.075*
C7	0.6845 (4)	0.44177 (10)	0.8545 (3)	0.0774 (9)
H7	0.7240	0.4680	0.9125	0.093*
C8	0.5126 (3)	0.41215 (9)	0.6685 (3)	0.0690 (8)
H8	0.4291	0.4172	0.5919	0.083*
C9	0.5716 (3)	0.36519 (8)	0.6935 (3)	0.0529 (7)
H9	0.5275	0.3394	0.6357	0.063*
C10	0.6875 (3)	0.12421 (7)	0.8693 (2)	0.0472 (6)
H10A	0.7817	0.1124	0.8418	0.057*
H10B	0.7188	0.1342	0.9648	0.057*
C11	0.5630 (3)	0.08400 (8)	0.8510 (2)	0.0443 (6)
C12	0.5488 (3)	0.05264 (9)	0.7392 (3)	0.0592 (7)
H12	0.6183	0.0560	0.6815	0.071*
C13	0.4334 (4)	0.01686 (9)	0.7133 (3)	0.0687 (8)
H13	0.4248	−0.0038	0.6379	0.082*
C14	0.3317 (3)	0.01133 (9)	0.7966 (3)	0.0660 (8)
H14	0.2519	−0.0126	0.7777	0.079*
C15	0.3473 (3)	0.04123 (8)	0.9091 (3)	0.0566 (7)
H15	0.2794	0.0367	0.9677	0.068*
C16	0.4617 (3)	0.07813 (8)	0.9376 (2)	0.0446 (6)
C17	0.4698 (3)	0.11019 (7)	1.0609 (2)	0.0502 (6)
H17A	0.5805	0.1184	1.1017	0.060*
H17B	0.4283	0.0921	1.1285	0.060*
C18	0.4950 (3)	0.21357 (8)	1.0767 (2)	0.0380 (5)
C19	0.7376 (3)	0.24131 (9)	1.1805 (2)	0.0484 (6)
H19	0.8442	0.2358	1.2238	0.058*
C20	0.6847 (3)	0.28872 (8)	1.1637 (2)	0.0446 (6)
H20	0.7523	0.3151	1.1955	0.053*
C21	0.5267 (3)	0.29608 (8)	1.0977 (2)	0.0393 (5)
C22	0.4562 (3)	0.34572 (8)	1.0709 (2)	0.0399 (5)
C23	0.5154 (3)	0.38590 (9)	1.1509 (3)	0.0589 (7)
H23	0.6024	0.3823	1.2253	0.071*
C24	0.4452 (4)	0.43133 (9)	1.1201 (3)	0.0701 (9)
H24	0.4868	0.4579	1.1761	0.084*
C25	0.3284 (3)	0.35403 (8)	0.9626 (2)	0.0497 (6)
H25	0.2835	0.3282	0.9052	0.060*
C26	0.2679 (3)	0.40072 (9)	0.9402 (3)	0.0597 (7)
H26	0.1816	0.4054	0.8656	0.072*
N1	0.8822 (2)	0.21295 (7)	0.89261 (18)	0.0458 (5)
N2	0.6713 (2)	0.26820 (6)	0.79073 (17)	0.0405 (5)
N3	0.5667 (3)	0.45081 (8)	0.7465 (3)	0.0771 (8)
N4	0.6443 (2)	0.20240 (7)	1.13813 (19)	0.0463 (5)
N5	0.4294 (2)	0.25802 (6)	1.05275 (17)	0.0394 (5)
N6	0.3221 (3)	0.43947 (7)	1.0157 (2)	0.0640 (6)
S1	0.60063 (8)	0.17575 (2)	0.76342 (6)	0.04810 (19)
S2	0.35623 (8)	0.16649 (2)	1.01669 (6)	0.04634 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0353 (14)	0.0411 (13)	0.0382 (13)	−0.0043 (11)	0.0074 (11)	0.0000 (10)
C2	0.0363 (16)	0.0586 (16)	0.0487 (15)	−0.0038 (12)	0.0005 (12)	0.0005 (12)
C3	0.0409 (16)	0.0496 (15)	0.0480 (15)	−0.0112 (12)	0.0031 (12)	−0.0033 (11)
C4	0.0424 (15)	0.0443 (13)	0.0377 (13)	−0.0058 (12)	0.0116 (11)	−0.0023 (10)
C5	0.0423 (16)	0.0436 (14)	0.0462 (14)	−0.0055 (11)	0.0131 (12)	−0.0066 (11)
C6	0.068 (2)	0.0518 (16)	0.0583 (17)	−0.0030 (15)	−0.0019 (14)	−0.0126 (13)
C7	0.090 (3)	0.0455 (17)	0.086 (2)	−0.0035 (16)	−0.001 (2)	−0.0243 (15)
C8	0.063 (2)	0.0504 (16)	0.081 (2)	0.0088 (14)	−0.0070 (16)	−0.0122 (15)
C9	0.0461 (17)	0.0422 (14)	0.0656 (17)	−0.0020 (12)	0.0036 (14)	−0.0122 (12)
C10	0.0394 (15)	0.0401 (13)	0.0559 (15)	0.0036 (11)	−0.0010 (12)	0.0066 (11)
C11	0.0447 (16)	0.0305 (12)	0.0509 (15)	0.0019 (11)	−0.0025 (12)	0.0012 (11)
C12	0.064 (2)	0.0480 (15)	0.0640 (18)	−0.0002 (14)	0.0131 (15)	−0.0030 (13)
C13	0.079 (2)	0.0455 (16)	0.072 (2)	−0.0027 (15)	−0.0014 (18)	−0.0151 (14)
C14	0.058 (2)	0.0367 (15)	0.094 (2)	−0.0075 (13)	−0.0005 (17)	−0.0006 (15)
C15	0.0512 (18)	0.0380 (14)	0.079 (2)	0.0012 (12)	0.0129 (15)	0.0064 (13)
C16	0.0457 (16)	0.0304 (12)	0.0526 (15)	0.0027 (11)	0.0016 (12)	0.0056 (11)
C17	0.0563 (17)	0.0387 (13)	0.0527 (16)	0.0057 (12)	0.0071 (13)	0.0101 (11)
C18	0.0354 (15)	0.0429 (13)	0.0355 (13)	0.0000 (11)	0.0084 (11)	−0.0030 (10)
C19	0.0335 (15)	0.0601 (16)	0.0471 (15)	0.0018 (13)	0.0005 (12)	0.0007 (12)
C20	0.0357 (15)	0.0464 (14)	0.0473 (14)	−0.0037 (11)	0.0014 (12)	−0.0047 (11)
C21	0.0379 (14)	0.0453 (13)	0.0340 (13)	−0.0012 (11)	0.0070 (11)	−0.0043 (10)
C22	0.0364 (14)	0.0410 (13)	0.0417 (13)	−0.0033 (11)	0.0080 (11)	−0.0054 (10)
C23	0.0475 (17)	0.0524 (16)	0.0654 (18)	0.0002 (13)	−0.0096 (14)	−0.0141 (13)
C24	0.065 (2)	0.0455 (16)	0.088 (2)	−0.0040 (14)	−0.0062 (17)	−0.0218 (14)
C25	0.0514 (17)	0.0407 (14)	0.0511 (15)	0.0003 (12)	0.0003 (13)	−0.0089 (11)
C26	0.0584 (19)	0.0521 (16)	0.0590 (17)	0.0073 (14)	−0.0057 (14)	−0.0017 (13)
N1	0.0354 (13)	0.0505 (12)	0.0475 (12)	−0.0011 (10)	0.0016 (10)	0.0037 (9)
N2	0.0357 (12)	0.0397 (11)	0.0440 (11)	−0.0041 (9)	0.0054 (9)	−0.0016 (9)
N3	0.079 (2)	0.0508 (14)	0.0889 (19)	0.0089 (13)	−0.0057 (15)	−0.0148 (13)
N4	0.0392 (13)	0.0472 (11)	0.0494 (12)	0.0050 (10)	0.0041 (10)	0.0038 (9)
N5	0.0350 (12)	0.0394 (11)	0.0420 (11)	0.0016 (9)	0.0053 (9)	−0.0027 (8)
N6	0.0645 (17)	0.0434 (13)	0.0754 (16)	0.0052 (11)	−0.0007 (13)	−0.0055 (11)
S1	0.0409 (4)	0.0417 (3)	0.0538 (4)	−0.0057 (3)	−0.0044 (3)	0.0051 (3)
S2	0.0425 (4)	0.0402 (3)	0.0539 (4)	−0.0003 (3)	0.0067 (3)	−0.0024 (3)

Geometric parameters (Å, º) top

C1—N2	1.328 (2)	C13—H13	0.9300
C1—N1	1.331 (3)	C14—C15	1.369 (3)
C1—S1	1.748 (2)	C14—H14	0.9300
C2—N1	1.329 (3)	C15—C16	1.385 (3)
C2—C3	1.364 (3)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.500 (3)
C3—C4	1.381 (3)	C17—S2	1.810 (2)
C3—H3	0.9300	C17—H17A	0.9700
C4—N2	1.338 (2)	C17—H17B	0.9700
C4—C5	1.478 (3)	C18—N4	1.323 (3)
C5—C6	1.369 (3)	C18—N5	1.328 (2)
C5—C9	1.375 (3)	C18—S2	1.754 (2)
C6—C7	1.371 (3)	C19—N4	1.333 (3)
C6—H6	0.9300	C19—C20	1.360 (3)
C7—N3	1.320 (3)	C19—H19	0.9300
C7—H7	0.9300	C20—C21	1.379 (3)
C8—N3	1.324 (3)	C20—H20	0.9300
C8—C9	1.372 (3)	C21—N5	1.339 (2)
C8—H8	0.9300	C21—C22	1.474 (3)
C9—H9	0.9300	C22—C25	1.369 (3)
C10—C11	1.509 (3)	C22—C23	1.377 (3)
C10—S1	1.807 (2)	C23—C24	1.374 (3)
C10—H10A	0.9700	C23—H23	0.9300
C10—H10B	0.9700	C24—N6	1.321 (3)
C11—C16	1.377 (3)	C24—H24	0.9300
C11—C12	1.389 (3)	C25—C26	1.367 (3)
C12—C13	1.368 (3)	C25—H25	0.9300
C12—H12	0.9300	C26—N6	1.314 (3)
C13—C14	1.354 (4)	C26—H26	0.9300

N2—C1—N1	127.8 (2)	C14—C15—H15	119.2
N2—C1—S1	113.12 (17)	C16—C15—H15	119.2
N1—C1—S1	119.04 (17)	C11—C16—C15	118.6 (2)
N1—C2—C3	123.0 (2)	C11—C16—C17	122.7 (2)
N1—C2—H2	118.5	C15—C16—C17	118.7 (2)
C3—C2—H2	118.5	C16—C17—S2	111.68 (15)
C2—C3—C4	118.2 (2)	C16—C17—H17A	109.3
C2—C3—H3	120.9	S2—C17—H17A	109.3
C4—C3—H3	120.9	C16—C17—H17B	109.3
N2—C4—C3	120.2 (2)	S2—C17—H17B	109.3
N2—C4—C5	117.2 (2)	H17A—C17—H17B	107.9
C3—C4—C5	122.6 (2)	N4—C18—N5	128.1 (2)
C6—C5—C9	116.6 (2)	N4—C18—S2	120.10 (17)
C6—C5—C4	121.9 (2)	N5—C18—S2	111.83 (17)
C9—C5—C4	121.5 (2)	N4—C19—C20	123.3 (2)
C5—C6—C7	119.8 (2)	N4—C19—H19	118.4
C5—C6—H6	120.1	C20—C19—H19	118.4
C7—C6—H6	120.1	C19—C20—C21	117.4 (2)
N3—C7—C6	124.2 (2)	C19—C20—H20	121.3
N3—C7—H7	117.9	C21—C20—H20	121.3
C6—C7—H7	117.9	N5—C21—C20	121.2 (2)
N3—C8—C9	124.2 (2)	N5—C21—C22	116.3 (2)
N3—C8—H8	117.9	C20—C21—C22	122.4 (2)
C9—C8—H8	117.9	C25—C22—C23	116.7 (2)
C8—C9—C5	119.5 (2)	C25—C22—C21	120.9 (2)
C8—C9—H9	120.3	C23—C22—C21	122.4 (2)
C5—C9—H9	120.3	C24—C23—C22	119.7 (2)
C11—C10—S1	107.66 (15)	C24—C23—H23	120.1
C11—C10—H10A	110.2	C22—C23—H23	120.1
S1—C10—H10A	110.2	N6—C24—C23	123.7 (2)
C11—C10—H10B	110.2	N6—C24—H24	118.1
S1—C10—H10B	110.2	C23—C24—H24	118.1
H10A—C10—H10B	108.5	C26—C25—C22	119.1 (2)
C16—C11—C12	119.3 (2)	C26—C25—H25	120.4
C16—C11—C10	122.9 (2)	C22—C25—H25	120.4
C12—C11—C10	117.7 (2)	N6—C26—C25	125.1 (2)
C13—C12—C11	120.6 (3)	N6—C26—H26	117.4
C13—C12—H12	119.7	C25—C26—H26	117.4
C11—C12—H12	119.7	C2—N1—C1	114.35 (19)
C14—C13—C12	120.5 (3)	C1—N2—C4	116.4 (2)
C14—C13—H13	119.8	C7—N3—C8	115.6 (2)
C12—C13—H13	119.8	C18—N4—C19	114.42 (19)
C13—C14—C15	119.4 (3)	C18—N5—C21	115.62 (19)
C13—C14—H14	120.3	C26—N6—C24	115.6 (2)
C15—C14—H14	120.3	C1—S1—C10	103.16 (11)
C14—C15—C16	121.6 (3)	C18—S2—C17	104.16 (11)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀N₆S₂
M_r	480.62
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	8.6078 (11), 27.102 (3), 10.0282 (12)
β (°)	103.661 (2)
V (Å³)	2273.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.32 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.917, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	13064, 4903, 3067
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.108, 0.90
No. of reflections	4903
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.22

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors are indebted to the National Natural Science Foundationof China (grant No. 20801011) for financial support.

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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