2-[3-Acetyl-5-(2-chloro-3-pyrid­yl)-2-methyl-2,3-dihydro-1,3,4-oxadiazol-2-yl]-4-fluoro­phenyl acetate

Qin, Q.; Xu, L.J.; Pan, L.F.; Chen, S.Q.; Song, Q.B.

doi:10.1107/S1600536809015323

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1181

doi:10.1107/S1600536809015323

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2-[3-Acetyl-5-(2-chloro-3-pyridyl)-2-methyl-2,3-dihydro-1,3,4-oxadiazol-2-yl]-4-fluorophenyl acetate

Quan Qin,^a Li Juan Xu,^a Li Fang Pan,^a Shui Qing Chen ^a and Qing Bao Song ^a ^*

^aThe State Key Laboratory Breeding Base of Green Chemistry–Synthesis Technology, College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: qbsong@zjut.edu.cn

(Received 30 March 2009; accepted 24 April 2009; online 30 April 2009)

In the title compound, C₁₈H₁₅ClFN₃O₄, the dihedral angle between the substituted pyridine ring and the oxadiazoline ring is 9.73 (19)° and the acyl group is coplanar with the oxadiazoline ring [O—C—N—C torsion angle = −2.1 (3)°]. Furthermore, the substituted benzene ring is almost orthogonal with the oxadiazoline ring, the dihedral angle between them being 87.56 (18)°.

Related literature

For background to 1,3,4-oxadiazoline derivatives and related structures, see: Song et al. (2006a ,b ); Pan et al. (2007 ). For the pharmacological properties of 2,5-disubstituted 1,3,4-oxadiazolines, see: Chimirri et al. (1994 , 1996 ); Dogan et al. (1998 ).

Experimental

Crystal data

C₁₈H₁₅ClFN₃O₄
M_r = 391.78
Monoclinic, P 2₁ /n
a = 10.120 (2) Å
b = 13.900 (3) Å
c = 13.320 (3) Å
β = 102.14 (3)°
V = 1831.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.971, T_max = 0.981
9882 measured reflections
3403 independent reflections
2394 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.121
S = 1.00
3403 reflections
248 parameters
H-atom parameters not refined
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015323/tk2411sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015323/tk2411Isup2.hkl

checkCIF report

Comment top

In continuation of our study of 1,3,4-oxadiazoline derivatives (Song et al., 2006a,b; Pan et al., 2007), which possess a wide range of pharmaceutical activities (Chimirri et al., 1994, 1996; Dogan et al., 1998), a series of new 1,3,4-oxadiazoline derivatives have been prepared. We present herein the crystal structure of the title compound, (I).

In (I), Fig. 1, the molecule is twisted about the C8—C9 bond. Within the five-membered oxadiazoline ring, there is a formal C13===N1 double bond (1.282 (3) Å). The bond distance of C13—O4 (1.360 (2) Å) is considerably shorter than the of C9—O4 bond (1.452 (2) Å), suggesting some delocalization of π-electron density over the O4—C13—N1 chromophore.

Related literature top

For background to 1,3,4-oxadiazoline derivatives and related structures, see: Song et al. (2006a,b); Pan et al. (2007). For some pharmacological properties of 2,5-disubstituted 1,3,4-oxadiazolines, see: Chimirri et al. (1994, 1996); Dogan et al. (1998).

Experimental top

A solution of 2-chloro-N'-(1-(5-fluoro-2-hydroxyphenyl)ethylidene) nicotinohydrazide (0.5 g, 1.62 mmol) in acetic anhydride (10 ml) was refluxed until the reaction was finished. The acetic anhydride was distilled under vacuum. The residue was recrystallized from ethanol (10 ml). Colorless crystals (0.46 g) were obtained by slow evaporation of an ethanol solution of (I) after 2 days at room temperature.

Computing details top

Data collection: APEX2 (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms are represented by circles of arbitrary size.

2-[3-Acetyl-5-(2-chloro-3-pyridyl)-2-methyl-2,3-dihydro-1,3,4-oxadiazol- 2-yl]-4-fluorophenyl acetate top

Crystal data top

C₁₈H₁₅ClFN₃O₄	F(000) = 808
M_r = 391.78	D_x = 1.421 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3403 reflections
a = 10.120 (2) Å	θ = 2.1–25.5°
b = 13.900 (3) Å	µ = 0.25 mm⁻¹
c = 13.320 (3) Å	T = 293 K
β = 102.14 (3)°	Block, colorless
V = 1831.8 (6) Å³	0.12 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3403 independent reflections
Radiation source: fine-focus sealed tube	2394 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→7
T_min = 0.971, T_max = 0.981	k = −16→16
9882 measured reflections	l = −16→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters not refined
S = 1.00	w = 1/[σ²(F_o²) + (0.06P)² + 0.3383P] where P = (F_o² + 2F_c²)/3
3403 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₁₅ClFN₃O₄	V = 1831.8 (6) Å³
M_r = 391.78	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.120 (2) Å	µ = 0.25 mm⁻¹
b = 13.900 (3) Å	T = 293 K
c = 13.320 (3) Å	0.12 × 0.10 × 0.08 mm
β = 102.14 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3403 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2394 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.981	R_int = 0.026
9882 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.121	H-atom parameters not refined
S = 1.00	Δρ_max = 0.22 e Å⁻³
3403 reflections	Δρ_min = −0.22 e Å⁻³
248 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	0.0490 (3)	0.1369 (2)	0.5790 (2)	0.0842 (8)
H1A	−0.0049	0.1943	0.5694	0.126*
H1B	0.0010	0.0859	0.5383	0.126*
H1C	0.1328	0.1485	0.5580	0.126*
C2	0.0772 (2)	0.10902 (17)	0.6890 (2)	0.0686 (6)
C3	0.1358 (2)	−0.02657 (15)	0.79837 (16)	0.0566 (5)
C4	0.0293 (3)	−0.04387 (16)	0.8454 (2)	0.0702 (7)
H4	−0.0576	−0.0247	0.8140	0.084*
C5	0.0520 (3)	−0.08956 (18)	0.9390 (2)	0.0778 (7)
H5	−0.0187	−0.1021	0.9718	0.093*
C6	0.1815 (3)	−0.11600 (17)	0.98264 (17)	0.0729 (7)
C7	0.2892 (3)	−0.09887 (15)	0.93740 (16)	0.0627 (6)
H7	0.3758	−0.1177	0.9699	0.075*
C8	0.2675 (2)	−0.05317 (14)	0.84270 (15)	0.0523 (5)
C9	0.3835 (2)	−0.03837 (14)	0.78801 (14)	0.0517 (5)
C10	0.5212 (2)	−0.07353 (16)	0.84381 (18)	0.0655 (6)
H10A	0.5183	−0.1419	0.8534	0.098*
H10B	0.5454	−0.0425	0.9095	0.098*
H10C	0.5872	−0.0585	0.8039	0.098*
C11	0.4183 (3)	0.23549 (16)	0.76258 (19)	0.0731 (7)
H11A	0.3303	0.2645	0.7478	0.110*
H11B	0.4494	0.2268	0.6999	0.110*
H11C	0.4801	0.2765	0.8080	0.110*
C12	0.4110 (2)	0.14036 (15)	0.81247 (16)	0.0551 (5)
C13	0.35464 (19)	−0.02406 (16)	0.61505 (14)	0.0512 (5)
C14	0.3289 (2)	−0.06543 (17)	0.51150 (15)	0.0561 (5)
C15	0.3246 (2)	−0.16524 (19)	0.50291 (18)	0.0692 (6)
H15	0.3420	−0.2032	0.5617	0.083*
C16	0.2944 (2)	−0.2080 (2)	0.4075 (2)	0.0806 (8)
H16	0.2913	−0.2746	0.4009	0.097*
C17	0.2691 (3)	−0.1500 (3)	0.3232 (2)	0.0896 (9)
H17	0.2472	−0.1791	0.2590	0.107*
C18	0.3038 (2)	−0.0137 (2)	0.41987 (16)	0.0655 (6)
Cl1	0.30866 (7)	0.11042 (5)	0.41760 (5)	0.0845 (3)
F1	0.2064 (2)	−0.16130 (13)	1.07494 (10)	0.1092 (6)
N1	0.37927 (17)	0.06330 (13)	0.64394 (12)	0.0543 (4)
N2	0.39054 (17)	0.06139 (12)	0.75037 (12)	0.0525 (4)
N3	0.2739 (2)	−0.0537 (2)	0.32705 (14)	0.0793 (6)
O1	0.10784 (15)	0.01308 (10)	0.69914 (11)	0.0612 (4)
O2	0.42063 (17)	0.13026 (11)	0.90474 (11)	0.0697 (5)
O3	0.0761 (2)	0.15939 (13)	0.76138 (16)	0.0960 (6)
O4	0.34983 (15)	−0.08897 (10)	0.69061 (10)	0.0569 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0707 (17)	0.0814 (18)	0.097 (2)	0.0185 (13)	0.0106 (14)	0.0250 (15)
C2	0.0516 (13)	0.0587 (15)	0.0921 (19)	0.0046 (11)	0.0072 (12)	−0.0006 (14)
C3	0.0683 (15)	0.0453 (11)	0.0562 (12)	−0.0010 (10)	0.0132 (11)	−0.0100 (9)
C4	0.0750 (16)	0.0595 (15)	0.0802 (17)	−0.0053 (12)	0.0258 (13)	−0.0181 (12)
C5	0.098 (2)	0.0677 (16)	0.0785 (18)	−0.0171 (15)	0.0424 (16)	−0.0228 (14)
C6	0.116 (2)	0.0610 (15)	0.0452 (13)	−0.0158 (14)	0.0260 (14)	−0.0094 (10)
C7	0.0875 (17)	0.0523 (13)	0.0470 (12)	−0.0097 (11)	0.0112 (12)	−0.0046 (10)
C8	0.0686 (14)	0.0409 (11)	0.0462 (11)	−0.0038 (9)	0.0097 (10)	−0.0070 (8)
C9	0.0636 (13)	0.0448 (11)	0.0434 (11)	0.0005 (9)	0.0036 (9)	0.0021 (8)
C10	0.0662 (14)	0.0631 (14)	0.0630 (14)	0.0084 (11)	0.0038 (11)	0.0152 (11)
C11	0.0900 (18)	0.0493 (13)	0.0749 (16)	−0.0044 (12)	0.0058 (13)	0.0103 (11)
C12	0.0573 (13)	0.0493 (12)	0.0531 (13)	0.0000 (9)	−0.0012 (10)	0.0032 (9)
C13	0.0449 (11)	0.0609 (13)	0.0457 (11)	0.0075 (10)	0.0048 (9)	0.0037 (10)
C14	0.0425 (11)	0.0771 (15)	0.0474 (12)	0.0085 (10)	0.0065 (9)	−0.0007 (10)
C15	0.0611 (14)	0.0862 (18)	0.0574 (14)	0.0141 (12)	0.0058 (11)	−0.0118 (12)
C16	0.0746 (17)	0.095 (2)	0.0675 (17)	0.0166 (14)	0.0046 (13)	−0.0188 (14)
C17	0.0727 (18)	0.132 (3)	0.0597 (17)	0.0181 (18)	0.0046 (13)	−0.0288 (17)
C18	0.0463 (12)	0.0983 (18)	0.0509 (13)	0.0108 (11)	0.0077 (10)	0.0046 (12)
Cl1	0.0910 (5)	0.0999 (5)	0.0607 (4)	0.0095 (4)	0.0117 (3)	0.0222 (3)
F1	0.1671 (18)	0.1102 (13)	0.0567 (9)	−0.0254 (11)	0.0381 (10)	0.0077 (8)
N1	0.0541 (10)	0.0628 (12)	0.0431 (9)	0.0031 (8)	0.0033 (8)	0.0088 (8)
N2	0.0628 (11)	0.0474 (10)	0.0429 (9)	0.0000 (8)	0.0011 (8)	0.0065 (7)
N3	0.0658 (13)	0.123 (2)	0.0473 (12)	0.0129 (13)	0.0071 (9)	−0.0021 (11)
O1	0.0643 (9)	0.0546 (9)	0.0614 (9)	0.0060 (7)	0.0060 (7)	−0.0009 (7)
O2	0.0934 (12)	0.0583 (9)	0.0497 (9)	−0.0047 (8)	−0.0023 (8)	0.0010 (7)
O3	0.1075 (15)	0.0635 (11)	0.1116 (16)	0.0128 (10)	0.0107 (12)	−0.0142 (11)
O4	0.0735 (10)	0.0501 (8)	0.0461 (8)	0.0030 (7)	0.0102 (7)	−0.0016 (6)

Geometric parameters (Å, º) top

C1—C2	1.484 (4)	C10—H10B	0.9600
C1—H1A	0.9600	C10—H10C	0.9600
C1—H1B	0.9600	C11—C12	1.489 (3)
C1—H1C	0.9600	C11—H11A	0.9600
C2—O3	1.194 (3)	C11—H11B	0.9600
C2—O1	1.369 (3)	C11—H11C	0.9600
C3—C4	1.377 (3)	C12—O2	1.220 (2)
C3—C8	1.390 (3)	C12—N2	1.364 (3)
C3—O1	1.405 (2)	C13—N1	1.282 (3)
C4—C5	1.375 (3)	C13—O4	1.360 (2)
C4—H4	0.9300	C13—C14	1.466 (3)
C5—C6	1.367 (4)	C14—C15	1.392 (3)
C5—H5	0.9300	C14—C18	1.393 (3)
C6—F1	1.357 (3)	C15—C16	1.377 (3)
C6—C7	1.373 (3)	C15—H15	0.9300
C7—C8	1.388 (3)	C16—C17	1.362 (4)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.520 (3)	C17—N3	1.340 (4)
C9—O4	1.452 (2)	C17—H17	0.9300
C9—N2	1.481 (2)	C18—N3	1.331 (3)
C9—C10	1.516 (3)	C18—Cl1	1.727 (3)
C10—H10A	0.9600	N1—N2	1.398 (2)

C2—C1—H1A	109.5	H10A—C10—H10C	109.5
C2—C1—H1B	109.5	H10B—C10—H10C	109.5
H1A—C1—H1B	109.5	C12—C11—H11A	109.5
C2—C1—H1C	109.5	C12—C11—H11B	109.5
H1A—C1—H1C	109.5	H11A—C11—H11B	109.5
H1B—C1—H1C	109.5	C12—C11—H11C	109.5
O3—C2—O1	122.1 (2)	H11A—C11—H11C	109.5
O3—C2—C1	127.7 (2)	H11B—C11—H11C	109.5
O1—C2—C1	110.2 (2)	O2—C12—N2	119.22 (19)
C4—C3—C8	122.2 (2)	O2—C12—C11	123.4 (2)
C4—C3—O1	118.3 (2)	N2—C12—C11	117.36 (19)
C8—C3—O1	119.31 (19)	N1—C13—O4	116.17 (17)
C5—C4—C3	119.7 (3)	N1—C13—C14	129.68 (19)
C5—C4—H4	120.1	O4—C13—C14	114.15 (18)
C3—C4—H4	120.1	C15—C14—C18	116.4 (2)
C6—C5—C4	118.2 (2)	C15—C14—C13	117.68 (19)
C6—C5—H5	120.9	C18—C14—C13	125.8 (2)
C4—C5—H5	120.9	C16—C15—C14	120.2 (2)
F1—C6—C5	119.3 (3)	C16—C15—H15	119.9
F1—C6—C7	117.7 (3)	C14—C15—H15	119.9
C5—C6—C7	123.0 (2)	C17—C16—C15	118.2 (3)
C6—C7—C8	119.4 (2)	C17—C16—H16	120.9
C6—C7—H7	120.3	C15—C16—H16	120.9
C8—C7—H7	120.3	N3—C17—C16	124.1 (2)
C7—C8—C3	117.5 (2)	N3—C17—H17	118.0
C7—C8—C9	120.5 (2)	C16—C17—H17	118.0
C3—C8—C9	121.92 (18)	N3—C18—C14	124.3 (3)
O4—C9—N2	99.78 (14)	N3—C18—Cl1	113.72 (19)
O4—C9—C10	107.50 (17)	C14—C18—Cl1	122.02 (18)
N2—C9—C10	111.29 (17)	C13—N1—N2	104.80 (16)
O4—C9—C8	107.64 (16)	C12—N2—N1	124.70 (17)
N2—C9—C8	112.70 (16)	C12—N2—C9	124.06 (16)
C10—C9—C8	116.38 (17)	N1—N2—C9	111.19 (15)
C9—C10—H10A	109.5	C18—N3—C17	116.8 (2)
C9—C10—H10B	109.5	C2—O1—C3	118.16 (18)
H10A—C10—H10B	109.5	C13—O4—C9	107.56 (15)
C9—C10—H10C	109.5

C8—C3—C4—C5	−0.5 (3)	C15—C14—C18—Cl1	−178.79 (16)
O1—C3—C4—C5	174.88 (19)	C13—C14—C18—Cl1	3.5 (3)
C3—C4—C5—C6	0.3 (3)	O4—C13—N1—N2	−1.3 (2)
C4—C5—C6—F1	−179.9 (2)	C14—C13—N1—N2	177.94 (19)
C4—C5—C6—C7	0.1 (4)	O2—C12—N2—N1	−179.27 (18)
F1—C6—C7—C8	179.65 (18)	C11—C12—N2—N1	1.6 (3)
C5—C6—C7—C8	−0.4 (3)	O2—C12—N2—C9	−2.1 (3)
C6—C7—C8—C3	0.2 (3)	C11—C12—N2—C9	178.74 (19)
C6—C7—C8—C9	−176.51 (19)	C13—N1—N2—C12	−177.06 (19)
C4—C3—C8—C7	0.2 (3)	C13—N1—N2—C9	5.5 (2)
O1—C3—C8—C7	−175.12 (17)	O4—C9—N2—C12	175.46 (18)
C4—C3—C8—C9	176.90 (19)	C10—C9—N2—C12	−71.3 (3)
O1—C3—C8—C9	1.5 (3)	C8—C9—N2—C12	61.5 (2)
C7—C8—C9—O4	119.08 (18)	O4—C9—N2—N1	−7.0 (2)
C3—C8—C9—O4	−57.5 (2)	C10—C9—N2—N1	106.21 (19)
C7—C8—C9—N2	−131.88 (18)	C8—C9—N2—N1	−120.95 (17)
C3—C8—C9—N2	51.6 (2)	C14—C18—N3—C17	−0.5 (3)
C7—C8—C9—C10	−1.6 (3)	Cl1—C18—N3—C17	179.67 (18)
C3—C8—C9—C10	−178.13 (18)	C16—C17—N3—C18	−0.8 (4)
N1—C13—C14—C15	170.8 (2)	O3—C2—O1—C3	1.4 (3)
O4—C13—C14—C15	−10.0 (3)	C1—C2—O1—C3	−179.18 (19)
N1—C13—C14—C18	−11.5 (3)	C4—C3—O1—C2	75.7 (2)
O4—C13—C14—C18	167.70 (19)	C8—C3—O1—C2	−108.7 (2)
C18—C14—C15—C16	−1.0 (3)	N1—C13—O4—C9	−3.4 (2)
C13—C14—C15—C16	176.9 (2)	C14—C13—O4—C9	177.29 (16)
C14—C15—C16—C17	−0.1 (4)	N2—C9—O4—C13	5.97 (19)
C15—C16—C17—N3	1.1 (4)	C10—C9—O4—C13	−110.18 (18)
C15—C14—C18—N3	1.4 (3)	C8—C9—O4—C13	123.72 (16)
C13—C14—C18—N3	−176.3 (2)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅ClFN₃O₄
M_r	391.78
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.120 (2), 13.900 (3), 13.320 (3)
β (°)	102.14 (3)
V (Å³)	1831.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.971, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	9882, 3403, 2394
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.121, 1.00
No. of reflections	3403
No. of parameters	248
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Key Discipline of Applied Chemistry, Zhejiang Province and the State Key Laboratory Breeding Base of Green Chemistry–Synthesis Technology, Zhejiang University of Technology (People's Republic of China).

References

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