6-Benz­yloxy-2-phenyl­pyridazin-3(2H)-one

Ju, Z.-Y.; Li, G.-C.; Li, C.; Wang, J.; Yang, F.-L.

doi:10.1107/S1600536812018776

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1646

doi:10.1107/S1600536812018776

Open

access

6-Benzyloxy-2-phenylpyridazin-3(2H)-one

Zhi-Yu Ju,^a Gong-Chun Li,^a Chao Li,^b Jie Wang ^b and Feng-Ling Yang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China, and ^bCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan Province 450001, People's Republic of China
^*Correspondence e-mail: 374107445@qq.com

(Received 11 April 2012; accepted 26 April 2012; online 5 May 2012)

In the title compound, C₁₇H₁₄N₂O₂, the central pyridazine ring forms dihedral angles of 47.29 (5) and 88.54 (5)° with the benzene rings, while the dihedral angle between the benzene rings is 62.68 (6)°. In the crystal, molecules are linked by two weak C—H⋯O hydrogen bonds and three weak C—H⋯π interactions.

Related literature

For applications of pyridazinone analogues as highly selective anti-HIV agents, see: Loksha et al. (2007 ), as pesticides, see: Li et al. (2005 ) and as herbicides, see: Xu et al. (2006 ). For a related structure, see: Ju et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₄N₂O₂
M_r = 278.30
Triclinic, $[P \overline 1]$
a = 7.390 (4) Å
b = 9.385 (5) Å
c = 10.587 (6) Å
α = 106.618 (7)°
β = 97.489 (6)°
γ = 101.098 (9)°
V = 676.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.982, T_max = 0.987
7083 measured reflections
3167 independent reflections
2103 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.070
S = 1.02
3167 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1ⁱ	0.95	2.54	3.389 (2)	149
C15—H15⋯O1ⁱⁱ	0.95	2.44	3.235 (2)	141
C4—H4⋯Cg2ⁱⁱⁱ	0.95	2.76	3.494 (2)	135
C9—H9⋯Cg2^iv	0.95	2.95	3.752 (2)	143
C13—H13⋯Cg1^v	0.95	2.63	3.456 (2)	145
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x+1, y-1, z; (iii) -x+1, -y+1, -z+2; (iv) -x+2, -y+1, -z+1; (v) x+1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018776/bg2457sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018776/bg2457Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018776/bg2457Isup3.cml

checkCIF report

Comment top

Pyridazinones represent an important class of biologically active compounds. Recently, a substantial number of pyridazinones have been reported to possess highly-selective anti-HIV agents (Loksha et al., 2007), pesticide(Li et al., 2005), highly herbicidal activity (Xu et al., 2006). In order to discover further biologically active Pyridazinone analogues, the title compound, (I), was synthesized, and its crystal structure determined (Fig. 1).

As a continuation of our studies on the crystal structures of Pyridazinone analogues (Ju et al., 2011), we report here the synthesis and crystal structure, an ellipsoid plot of which is shown in Fig. 1. The central pyridazine ring forms dihedral angles of 47.29 (5)° and 88.54 (5)° with the two benzene rings, while the dihedral angle between the two benzene rings is 62.68 (6)°. The structure is stabilized by two weak C—H···O and three C—H···Cg intermolecular hydrogen bonds (Cg's: centroids of the benzene rings) (Table 1).

Related literature top

For applications of pyridazinone analogues as highly selective anti-HIV agents, see: Loksha et al. (2007), as pesticides, see: Li et al. (2005) and as herbicides, see: Xu et al. (2006). For a related structure, see: Ju et al. (2011).

Experimental top

3-hydroxyl-1phenyl-6-pyridazone(0.94 g, 5 mmol), benzyl chloride(0.63 g, 5 mmol) and K₂CO₃ (0.69 g, 5 mmol) were added to absolute ethanol(30 ml). The mixture was stirred in the room temperature for 10 h. The suspension was filtered and the residue was washed with absolute ethanol. The title compound was recrystallized from the mother solution and single crystals of (I) were obtained by slow evaporation.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: CrystalStructure (Rigaku/MSC, 2005).

Figures top

Fig. 1. The asymmetric unit of the title compound, (I), with displacement ellipsoids drawn at the 30% probability level.

6-Benzyloxy-2-phenylpyridazin-3(2H)-one top

Crystal data top

C₁₇H₁₄N₂O₂	Z = 2
M_r = 278.30	F(000) = 292
Triclinic, P1	D_x = 1.365 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.390 (4) Å	Cell parameters from 2420 reflections
b = 9.385 (5) Å	θ = 2.0–27.9°
c = 10.587 (6) Å	µ = 0.09 mm⁻¹
α = 106.618 (7)°	T = 113 K
β = 97.489 (6)°	Prism, colorless
γ = 101.098 (9)°	0.20 × 0.18 × 0.14 mm
V = 676.9 (6) Å³

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3167 independent reflections
Radiation source: rotating anode	2103 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.037
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 2.1°
ω and ϕ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→12
T_min = 0.982, T_max = 0.987	l = −13→13
7083 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.014P)²] where P = (F_o² + 2F_c²)/3
3167 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₇H₁₄N₂O₂	γ = 101.098 (9)°
M_r = 278.30	V = 676.9 (6) Å³
Triclinic, P1	Z = 2
a = 7.390 (4) Å	Mo Kα radiation
b = 9.385 (5) Å	µ = 0.09 mm⁻¹
c = 10.587 (6) Å	T = 113 K
α = 106.618 (7)°	0.20 × 0.18 × 0.14 mm
β = 97.489 (6)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3167 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2103 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.987	R_int = 0.037
7083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.02	Δρ_max = 0.29 e Å⁻³
3167 reflections	Δρ_min = −0.21 e Å⁻³
190 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
O1	0.42844 (11)	0.94745 (8)	0.63170 (7)	0.0233 (2)
O2	0.77932 (11)	0.49972 (8)	0.63235 (8)	0.0216 (2)
N1	0.48299 (13)	0.75278 (10)	0.71052 (9)	0.0164 (2)
N2	0.57426 (13)	0.63946 (10)	0.71641 (9)	0.0175 (2)
C1	0.36869 (16)	0.78488 (12)	0.81087 (11)	0.0167 (3)
C2	0.18835 (17)	0.79994 (12)	0.77449 (12)	0.0201 (3)
H2	0.1387	0.7879	0.6836	0.024*
C3	0.08053 (17)	0.83289 (12)	0.87255 (12)	0.0220 (3)
H3	−0.0429	0.8447	0.8488	0.026*
C4	0.15216 (17)	0.84853 (12)	1.00468 (12)	0.0226 (3)
H4	0.0780	0.8708	1.0713	0.027*
C5	0.33193 (17)	0.83158 (12)	1.03932 (12)	0.0216 (3)
H5	0.3805	0.8414	1.1298	0.026*
C6	0.44193 (17)	0.80031 (12)	0.94267 (11)	0.0194 (3)
H6	0.5658	0.7896	0.9667	0.023*
C7	0.50525 (16)	0.84005 (12)	0.62487 (11)	0.0175 (3)
C8	0.62325 (15)	0.79457 (12)	0.52976 (11)	0.0187 (3)
H8	0.6404	0.8461	0.4653	0.022*
C9	0.70914 (16)	0.68125 (12)	0.53036 (11)	0.0190 (3)
H9	0.7855	0.6509	0.4669	0.023*
C10	0.68183 (16)	0.60737 (12)	0.63011 (11)	0.0172 (3)
C11	0.76814 (17)	0.43746 (13)	0.74356 (11)	0.0219 (3)
H11A	0.6432	0.3673	0.7289	0.026*
H11B	0.7866	0.5214	0.8293	0.026*
C12	0.91981 (16)	0.35233 (12)	0.74890 (11)	0.0178 (3)
C13	1.09241 (17)	0.42585 (13)	0.83407 (11)	0.0218 (3)
H13	1.1142	0.5302	0.8874	0.026*
C14	1.23333 (17)	0.34891 (13)	0.84226 (11)	0.0230 (3)
H14	1.3512	0.4006	0.9008	0.028*
C15	1.20271 (17)	0.19639 (13)	0.76516 (11)	0.0217 (3)
H15	1.2986	0.1428	0.7712	0.026*
C16	1.03045 (17)	0.12308 (13)	0.67916 (11)	0.0217 (3)
H16	1.0090	0.0189	0.6255	0.026*
C17	0.89004 (17)	0.19985 (12)	0.67083 (11)	0.0206 (3)
H17	0.7727	0.1484	0.6116	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0327 (5)	0.0207 (5)	0.0235 (5)	0.0139 (4)	0.0090 (4)	0.0113 (4)
O2	0.0276 (5)	0.0237 (5)	0.0227 (5)	0.0151 (4)	0.0099 (4)	0.0134 (4)
N1	0.0187 (6)	0.0172 (5)	0.0177 (5)	0.0093 (4)	0.0052 (5)	0.0083 (4)
N2	0.0189 (6)	0.0168 (5)	0.0198 (5)	0.0085 (4)	0.0041 (5)	0.0074 (4)
C1	0.0200 (7)	0.0130 (6)	0.0188 (7)	0.0044 (5)	0.0066 (5)	0.0062 (5)
C2	0.0241 (7)	0.0176 (6)	0.0199 (7)	0.0065 (5)	0.0040 (6)	0.0075 (5)
C3	0.0196 (7)	0.0181 (6)	0.0314 (8)	0.0078 (5)	0.0071 (6)	0.0096 (5)
C4	0.0290 (8)	0.0176 (7)	0.0243 (7)	0.0080 (6)	0.0129 (6)	0.0067 (5)
C5	0.0271 (8)	0.0199 (7)	0.0169 (7)	0.0034 (6)	0.0043 (6)	0.0061 (5)
C6	0.0202 (7)	0.0180 (6)	0.0209 (7)	0.0050 (5)	0.0038 (6)	0.0077 (5)
C7	0.0201 (7)	0.0170 (6)	0.0158 (6)	0.0044 (5)	0.0016 (5)	0.0067 (5)
C8	0.0224 (7)	0.0195 (6)	0.0165 (6)	0.0056 (5)	0.0052 (6)	0.0081 (5)
C9	0.0201 (7)	0.0215 (7)	0.0163 (7)	0.0053 (5)	0.0056 (5)	0.0062 (5)
C10	0.0185 (7)	0.0164 (6)	0.0170 (6)	0.0067 (5)	0.0012 (5)	0.0051 (5)
C11	0.0255 (8)	0.0243 (7)	0.0223 (7)	0.0104 (6)	0.0078 (6)	0.0132 (5)
C12	0.0210 (7)	0.0199 (6)	0.0185 (7)	0.0098 (5)	0.0081 (6)	0.0102 (5)
C13	0.0270 (8)	0.0166 (6)	0.0238 (7)	0.0074 (6)	0.0066 (6)	0.0074 (5)
C14	0.0194 (7)	0.0240 (7)	0.0257 (7)	0.0058 (6)	0.0014 (6)	0.0090 (6)
C15	0.0249 (7)	0.0259 (7)	0.0229 (7)	0.0151 (6)	0.0095 (6)	0.0128 (6)
C16	0.0322 (8)	0.0167 (6)	0.0186 (7)	0.0101 (6)	0.0071 (6)	0.0056 (5)
C17	0.0219 (7)	0.0216 (7)	0.0187 (7)	0.0052 (5)	0.0020 (5)	0.0080 (5)

Geometric parameters (Å, º) top

O1—C7	1.2379 (14)	C8—C9	1.3405 (15)
O2—C10	1.3526 (14)	C8—H8	0.9500
O2—C11	1.4611 (14)	C9—C10	1.4343 (16)
N1—N2	1.3758 (13)	C9—H9	0.9500
N1—C7	1.3899 (14)	C11—C12	1.5006 (16)
N1—C1	1.4429 (14)	C11—H11A	0.9900
N2—C10	1.2967 (14)	C11—H11B	0.9900
C1—C2	1.3836 (17)	C12—C13	1.3862 (16)
C1—C6	1.3850 (17)	C12—C17	1.3907 (16)
C2—C3	1.3911 (16)	C13—C14	1.3839 (16)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.3851 (17)	C14—C15	1.3875 (17)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.3829 (17)	C15—C16	1.3875 (16)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.3896 (16)	C16—C17	1.3799 (16)
C5—H5	0.9500	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.4432 (16)

C10—O2—C11	115.71 (9)	C8—C9—H9	121.1
N2—N1—C7	125.17 (10)	C10—C9—H9	121.1
N2—N1—C1	113.91 (9)	N2—C10—O2	119.85 (10)
C7—N1—C1	120.75 (10)	N2—C10—C9	124.22 (12)
C10—N2—N1	116.73 (10)	O2—C10—C9	115.93 (11)
C2—C1—C6	120.99 (11)	O2—C11—C12	107.55 (9)
C2—C1—N1	119.79 (11)	O2—C11—H11A	110.2
C6—C1—N1	119.22 (11)	C12—C11—H11A	110.2
C1—C2—C3	119.21 (11)	O2—C11—H11B	110.2
C1—C2—H2	120.4	C12—C11—H11B	110.2
C3—C2—H2	120.4	H11A—C11—H11B	108.5
C4—C3—C2	120.34 (12)	C13—C12—C17	119.09 (12)
C4—C3—H3	119.8	C13—C12—C11	119.69 (11)
C2—C3—H3	119.8	C17—C12—C11	121.21 (11)
C5—C4—C3	119.82 (11)	C14—C13—C12	120.71 (11)
C5—C4—H4	120.1	C14—C13—H13	119.6
C3—C4—H4	120.1	C12—C13—H13	119.6
C4—C5—C6	120.45 (12)	C13—C14—C15	120.09 (12)
C4—C5—H5	119.8	C13—C14—H14	120.0
C6—C5—H5	119.8	C15—C14—H14	120.0
C1—C6—C5	119.19 (12)	C14—C15—C16	119.22 (12)
C1—C6—H6	120.4	C14—C15—H15	120.4
C5—C6—H6	120.4	C16—C15—H15	120.4
O1—C7—N1	121.54 (11)	C17—C16—C15	120.69 (12)
O1—C7—C8	123.94 (10)	C17—C16—H16	119.7
N1—C7—C8	114.53 (11)	C15—C16—H16	119.7
C9—C8—C7	121.43 (11)	C16—C17—C12	120.20 (12)
C9—C8—H8	119.3	C16—C17—H17	119.9
C7—C8—H8	119.3	C12—C17—H17	119.9
C8—C9—C10	117.73 (11)

C7—N1—N2—C10	−3.67 (15)	N1—C7—C8—C9	−2.77 (16)
C1—N1—N2—C10	−178.83 (9)	C7—C8—C9—C10	−0.74 (16)
N2—N1—C1—C2	−134.36 (10)	N1—N2—C10—O2	178.41 (9)
C7—N1—C1—C2	50.24 (14)	N1—N2—C10—C9	−0.47 (16)
N2—N1—C1—C6	45.70 (13)	C11—O2—C10—N2	−5.75 (15)
C7—N1—C1—C6	−129.70 (12)	C11—O2—C10—C9	173.22 (9)
C6—C1—C2—C3	0.78 (16)	C8—C9—C10—N2	2.57 (17)
N1—C1—C2—C3	−179.16 (9)	C8—C9—C10—O2	−176.35 (9)
C1—C2—C3—C4	−0.80 (16)	C10—O2—C11—C12	−166.04 (9)
C2—C3—C4—C5	0.13 (16)	O2—C11—C12—C13	94.70 (12)
C3—C4—C5—C6	0.58 (16)	O2—C11—C12—C17	−86.01 (13)
C2—C1—C6—C5	−0.09 (16)	C17—C12—C13—C14	−0.35 (17)
N1—C1—C6—C5	179.85 (9)	C11—C12—C13—C14	178.96 (10)
C4—C5—C6—C1	−0.60 (16)	C12—C13—C14—C15	−0.22 (18)
N2—N1—C7—O1	−174.84 (10)	C13—C14—C15—C16	0.68 (17)
C1—N1—C7—O1	0.01 (17)	C14—C15—C16—C17	−0.59 (17)
N2—N1—C7—C8	5.19 (16)	C15—C16—C17—C12	0.02 (17)
C1—N1—C7—C8	−179.96 (9)	C13—C12—C17—C16	0.44 (17)
O1—C7—C8—C9	177.26 (11)	C11—C12—C17—C16	−178.85 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.95	2.54	3.389 (2)	149
C15—H15···O1ⁱⁱ	0.95	2.44	3.235 (2)	141
C4—H4···Cg2ⁱⁱⁱ	0.95	2.76	3.494 (2)	135
C9—H9···Cg2^iv	0.95	2.95	3.752 (2)	143
C13—H13···Cg1^v	0.95	2.63	3.456 (2)	145

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y−1, z; (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y+1, −z+1; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂O₂
M_r	278.30
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	7.390 (4), 9.385 (5), 10.587 (6)
α, β, γ (°)	106.618 (7), 97.489 (6), 101.098 (9)
V (Å³)	676.9 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.18 × 0.14

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.982, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	7083, 3167, 2103
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.070, 1.02
No. of reflections	3167
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.21

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.95	2.54	3.389 (2)	149
C15—H15···O1ⁱⁱ	0.95	2.44	3.235 (2)	141
C4—H4···Cg2ⁱⁱⁱ	0.95	2.76	3.494 (2)	135
C9—H9···Cg2^iv	0.95	2.95	3.752 (2)	143
C13—H13···Cg1^v	0.95	2.63	3.456 (2)	145

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y−1, z; (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y+1, −z+1; (v) x+1, y, z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant Nos. 20972143 and 20972130), the Natural Science Foundation of Henan Province Education Committee, China (No. 2010 A150021) and the Natural Science Foundation of Xuchang University (grant No. 2012064).

References

Ju, Z.-Y., Jiang, W.-X. & Yang, F.-L. (2011). Acta Cryst. E67, o1042. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, H. S., Ling, Y., Guo, Y. L., Yang, X. L. & Chen, F. H. (2005). Chin. J. Org. Chem. 25, 204–207. CAS Google Scholar
Loksha, Y. M., Pedersen, E. B., Colla, P. L. & Loddo, R. (2007). J. Heterocycl. Chem. 44, 1351–1356. CrossRef CAS Google Scholar
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, H., Zou, X. M. & Yang, H. Z. (2006). Pest Manag. Sci. 62, 522–530. Web of Science CSD CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1646

doi:10.1107/S1600536812018776

Open

access