3-[(E)-1-(Benzyl­oxyimino)­eth­yl]-7-(3-methyl­but-2-en­yloxy)-2H-chromen-2-one

Wang, H.; He, L.; Zheng, W.; Song, H.

doi:10.1107/S1600536811019015

organic compounds

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Volume 67| Part 6| June 2011| Page o1516

doi:10.1107/S1600536811019015

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3-[(E)-1-(Benzyloxyimino)ethyl]-7-(3-methylbut-2-enyloxy)-2H-chromen-2-one

Hui Wang,^a ^* Li-juan He,^a Wei-hua Zheng ^a and Hua-can Song ^b

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, People's Republic of China
^*Correspondence e-mail: huiwang@scnu.edu.cn

(Received 7 May 2011; accepted 19 May 2011; online 25 May 2011)

In the title compound, C₂₃H₂₃NO₄, the dihedral angle beween the chromen-2-one ring system and the benzene ring is 69.73 (10)° and the molecule adopts an E conformation with respect to the C=N double bond. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds occur, generating R₂²(12) loops.

Related literature

For background to the use of Schiff bases as chemosensors, see: Li et al. (2009 ).

Experimental

Crystal data

C₂₃H₂₃NO₄
M_r = 377.42
Triclinic, $[P \overline 1]$
a = 7.3038 (19) Å
b = 11.467 (3) Å
c = 12.184 (3) Å
α = 92.368 (3)°
β = 92.067 (3)°
γ = 102.340 (3)°
V = 995.0 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 273 K
0.26 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.978, T_max = 0.986
5604 measured reflections
3912 independent reflections
2341 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.155
S = 1.01
3912 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2ⁱ	0.93	2.43	3.338 (3)	167
Symmetry code: (i) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019015/hb5875sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019015/hb5875Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019015/hb5875Isup3.cml

checkCIF report

Comment top

Coumarin-derived Schiff bases have attracted attention as colorimetric chemosensors (Li et al., 2009). Herein, we report the crystal structure of the title compound, (I), Fig. 1, obtained by the reaction of 3-acetyl-7-(3-methylbut-2-enyloxy)-2H- chromen-2-one with benzyloxy-amine. Inversion dimers occur in the crystal, being linked by pairs of C—H···O hydrogen bonds (Table 1).

Related literature top

For background to the use of Schiff bases as chemosensors, see: Li et al. (2009).

Experimental top

A mixture of 3-acetyl-7-(3-methylbut-2-enyloxy)-2H-chromen-2-one (1 mmol) and benzyloxy- amine hydrochloride (1.2 mmol) in ethanol (15 ml) was heated at 313 K for 0.5 h, the solution pH was then maintained at a value of 7 by the addition of sodium carbonate(0.5 mmol). The reaction mixture was refluxed for 10 h at 333 K (monitored by TLC). After completion of the reaction, the solvent was removed under a vacuum. The crude product was purified by chromatography (ethyl acetate: petroleum ether = 3:1). The eluate was evaporated to give the title compound as colourless blocks (279 mg, 74%; m. p. 372–374 K). ESI-MS (m / z): [(M+Na)+] 400, [(M+H)+] 378; IR (KBr, cm-1) 3065, 2971, 2877, 1722, 1603, 1491, 1458, 1357, 1259, 1216, 1129, 981, 923, 772; 1H NMR(400 MHz, CDCl3, TMS) delta 7.79 (s, 1H), 7.40 (d, 1H, J = 8.4 Hz), 7.31–7.36 (m, 5H), 6.83 (dd, 1H, J = 2.8, 8.4 Hz), 6.79(d 1H, J = 2.8 Hz), 5.45–5.50 (m, 1H), 5.23 (s, 2H), 4.56(d, 2H, J = 6.8 Hz), 2.27 (s, 3H), 1.80 (s, 3H), 1.76 (s, 3H); 13 C NMR (100 MHz, CDCl3) delta 162.45, 160.08, 155.90, 154.33, 141.40, 137.72, 129.49, 128.96, 128.41, 128.33, 127.97, 127.84,127.42, 121.30, 118.59, 113.57, 112.43, 101.08, 76.21, 65.46, 25.83,18.30,14.61.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing in the title compound.
	Fig. 3. Part of the crystal structure of the title compound showing weak C—H···O hydrogen bonds as dashed lines.
	Fig. 4. The formation of the title compound.

3-[(E)-1-(Benzyloxyimino)ethyl]-7-(3-methylbut-2-enyloxy)- 2H-chromen-2-one top

Crystal data top

C₂₃H₂₃NO₄	Z = 2
M_r = 377.42	F(000) = 430.0
Triclinic, P1	D_x = 1.260 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3038 (19) Å	Cell parameters from 1391 reflections
b = 11.467 (3) Å	θ = 2.4–24.9°
c = 12.184 (3) Å	µ = 0.09 mm⁻¹
α = 92.368 (3)°	T = 273 K
β = 92.067 (3)°	Block, colorless
γ = 102.340 (3)°	0.26 × 0.18 × 0.16 mm
V = 995.0 (5) Å³

Data collection top

Bruker APEXII CCD diffractometer	3912 independent reflections
Radiation source: fine-focus sealed tube	2341 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 26.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→8
T_min = 0.978, T_max = 0.986	k = −10→14
5604 measured reflections	l = −14→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)] = 0.052	H-atom parameters constrained
wR(F²) = 0.155	w = 1/[σ²(F_o²) + (0.0644P)² + 0.1016P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.028
3912 reflections	Δρ_max = 0.18 e Å⁻³
257 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.049 (5)

Crystal data top

C₂₃H₂₃NO₄	γ = 102.340 (3)°
M_r = 377.42	V = 995.0 (5) Å³
Triclinic, P1	Z = 2
a = 7.3038 (19) Å	Mo Kα radiation
b = 11.467 (3) Å	µ = 0.09 mm⁻¹
c = 12.184 (3) Å	T = 273 K
α = 92.368 (3)°	0.26 × 0.18 × 0.16 mm
β = 92.067 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3912 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2341 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.986	R_int = 0.032
5604 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.01	Δρ_max = 0.18 e Å⁻³
3912 reflections	Δρ_min = −0.19 e Å⁻³
257 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
N1	0.4410 (2)	0.43803 (16)	0.26381 (14)	0.0548 (5)
O3	0.59306 (19)	0.46642 (13)	0.19438 (12)	0.0611 (4)
O2	0.3010 (2)	0.10766 (13)	0.38943 (12)	0.0622 (4)
O1	0.04470 (18)	0.14660 (12)	0.45666 (10)	0.0492 (4)
O4	−0.50894 (19)	0.21552 (13)	0.61925 (11)	0.0558 (4)
C19	0.9868 (3)	0.6503 (2)	0.19649 (18)	0.0627 (6)
H19	0.9821	0.6483	0.2726	0.075*
C18	1.1555 (3)	0.6776 (2)	0.1505 (2)	0.0776 (8)
H18	1.2648	0.6934	0.1952	0.093*
C17	1.1667 (4)	0.6820 (3)	0.0413 (3)	0.0852 (9)
H17	1.2835	0.7011	0.0107	0.102*
C16	1.0072 (5)	0.6584 (3)	−0.0255 (2)	0.0898 (9)
H16	1.0149	0.6616	−0.1014	0.108*
C15	0.8327 (4)	0.6296 (2)	0.0215 (2)	0.0743 (7)
H15	0.7235	0.6132	−0.0232	0.089*
C14	0.8222 (3)	0.62545 (18)	0.13341 (18)	0.0539 (6)
C13	0.6388 (4)	0.5931 (2)	0.1861 (3)	0.0872 (9)
H13B	0.6471	0.6325	0.2587	0.105*
H13A	0.5422	0.6184	0.1423	0.105*
C11	0.3842 (3)	0.32488 (19)	0.26814 (16)	0.0485 (5)
C12	0.4680 (4)	0.2348 (2)	0.2070 (2)	0.0742 (7)
H12C	0.5063	0.2642	0.1369	0.111*
H12A	0.3765	0.1611	0.1961	0.111*
H12B	0.5750	0.2214	0.2486	0.111*
C3	0.2208 (3)	0.28938 (17)	0.33767 (15)	0.0449 (5)
C2	0.1984 (3)	0.17731 (18)	0.39329 (15)	0.0462 (5)
C9	−0.0825 (3)	0.21796 (17)	0.47168 (14)	0.0418 (5)
C4	0.0943 (3)	0.35857 (18)	0.35299 (15)	0.0481 (5)
H4	0.1091	0.4300	0.3175	0.058*
C10	−0.0610 (3)	0.32596 (17)	0.42160 (15)	0.0437 (5)
C5	−0.1943 (3)	0.39482 (19)	0.44254 (17)	0.0530 (5)
H5	−0.1839	0.4680	0.4104	0.064*
C6	−0.3389 (3)	0.35666 (19)	0.50912 (17)	0.0529 (5)
H6	−0.4246	0.4042	0.5231	0.064*
C8	−0.2289 (3)	0.17562 (18)	0.53828 (15)	0.0460 (5)
H8	−0.2400	0.1022	0.5699	0.055*
C7	−0.3581 (3)	0.24560 (18)	0.55642 (15)	0.0458 (5)
C20	−0.5503 (3)	0.0961 (2)	0.65844 (17)	0.0564 (6)
H20B	−0.4576	0.0878	0.7150	0.068*
H20A	−0.5481	0.0381	0.5985	0.068*
C21	−0.7401 (3)	0.07576 (19)	0.70411 (16)	0.0536 (5)
H21	−0.8390	0.0794	0.6550	0.064*
C22	−0.7839 (3)	0.05328 (19)	0.80605 (16)	0.0516 (5)
C24	−0.6452 (4)	0.0473 (3)	0.89720 (19)	0.0908 (9)
H24C	−0.5213	0.0617	0.8696	0.136*
H24A	−0.6738	−0.0304	0.9268	0.136*
H24B	−0.6510	0.1069	0.9539	0.136*
C23	−0.9843 (3)	0.0309 (2)	0.8392 (2)	0.0740 (7)
H23B	−1.0643	0.0390	0.7770	0.111*
H23C	−0.9965	0.0879	0.8969	0.111*
H23A	−1.0200	−0.0484	0.8648	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0458 (10)	0.0545 (12)	0.0642 (11)	0.0066 (9)	0.0195 (8)	0.0119 (9)
O3	0.0547 (9)	0.0495 (10)	0.0799 (10)	0.0063 (7)	0.0285 (8)	0.0151 (7)
O2	0.0598 (9)	0.0552 (10)	0.0791 (10)	0.0235 (8)	0.0188 (8)	0.0198 (8)
O1	0.0493 (8)	0.0467 (9)	0.0545 (8)	0.0125 (7)	0.0135 (6)	0.0161 (6)
O4	0.0584 (9)	0.0500 (9)	0.0602 (9)	0.0102 (7)	0.0212 (7)	0.0094 (7)
C19	0.0675 (15)	0.0652 (16)	0.0569 (13)	0.0157 (13)	0.0105 (11)	0.0086 (11)
C18	0.0535 (15)	0.089 (2)	0.0876 (19)	0.0105 (14)	0.0042 (13)	0.0007 (15)
C17	0.0681 (18)	0.089 (2)	0.096 (2)	0.0059 (15)	0.0369 (16)	0.0044 (16)
C16	0.122 (3)	0.093 (2)	0.0524 (15)	0.0134 (19)	0.0287 (17)	0.0138 (14)
C15	0.0760 (18)	0.0710 (18)	0.0716 (16)	0.0083 (14)	−0.0149 (13)	0.0084 (13)
C14	0.0487 (13)	0.0434 (13)	0.0715 (14)	0.0097 (10)	0.0176 (11)	0.0137 (10)
C13	0.0692 (17)	0.0507 (16)	0.150 (3)	0.0176 (13)	0.0500 (17)	0.0331 (16)
C11	0.0480 (12)	0.0480 (13)	0.0491 (11)	0.0080 (10)	0.0081 (9)	0.0058 (9)
C12	0.0839 (18)	0.0575 (16)	0.0832 (17)	0.0131 (13)	0.0391 (14)	0.0051 (13)
C3	0.0458 (11)	0.0430 (12)	0.0453 (10)	0.0064 (9)	0.0075 (8)	0.0072 (9)
C2	0.0449 (11)	0.0469 (13)	0.0467 (11)	0.0082 (10)	0.0057 (9)	0.0072 (9)
C9	0.0435 (11)	0.0416 (12)	0.0412 (10)	0.0108 (9)	0.0031 (8)	0.0047 (8)
C4	0.0508 (12)	0.0435 (12)	0.0489 (11)	0.0060 (10)	0.0046 (9)	0.0111 (9)
C10	0.0431 (11)	0.0433 (12)	0.0436 (10)	0.0059 (9)	0.0032 (8)	0.0075 (9)
C5	0.0536 (13)	0.0454 (13)	0.0616 (13)	0.0110 (10)	0.0085 (10)	0.0146 (10)
C6	0.0519 (12)	0.0448 (13)	0.0649 (13)	0.0144 (10)	0.0097 (10)	0.0085 (10)
C8	0.0511 (12)	0.0427 (12)	0.0436 (10)	0.0069 (10)	0.0064 (9)	0.0084 (9)
C7	0.0465 (11)	0.0465 (12)	0.0425 (10)	0.0042 (9)	0.0101 (8)	0.0046 (9)
C20	0.0637 (14)	0.0540 (14)	0.0522 (12)	0.0108 (11)	0.0156 (10)	0.0106 (10)
C21	0.0486 (12)	0.0603 (14)	0.0501 (12)	0.0054 (10)	0.0072 (9)	0.0111 (10)
C22	0.0539 (13)	0.0507 (13)	0.0490 (11)	0.0066 (10)	0.0091 (9)	0.0062 (9)
C24	0.0810 (19)	0.136 (3)	0.0548 (14)	0.0192 (18)	0.0014 (13)	0.0171 (15)
C23	0.0656 (16)	0.0839 (19)	0.0709 (16)	0.0066 (14)	0.0209 (12)	0.0184 (13)

Geometric parameters (Å, º) top

N1—C11	1.279 (3)	C3—C4	1.354 (3)
N1—O3	1.4111 (19)	C3—C2	1.459 (3)
O3—C13	1.428 (3)	C9—C8	1.382 (2)
O2—C2	1.207 (2)	C9—C10	1.385 (3)
O1—C9	1.375 (2)	C4—C10	1.428 (3)
O1—C2	1.377 (2)	C4—H4	0.9300
O4—C7	1.356 (2)	C10—C5	1.402 (3)
O4—C20	1.443 (2)	C5—C6	1.363 (3)
C19—C18	1.353 (3)	C5—H5	0.9300
C19—C14	1.373 (3)	C6—C7	1.401 (3)
C19—H19	0.9300	C6—H6	0.9300
C18—C17	1.338 (3)	C8—C7	1.381 (3)
C18—H18	0.9300	C8—H8	0.9300
C17—C16	1.368 (4)	C20—C21	1.488 (3)
C17—H17	0.9300	C20—H20B	0.9700
C16—C15	1.396 (4)	C20—H20A	0.9700
C16—H16	0.9300	C21—C22	1.316 (3)
C15—C14	1.371 (3)	C21—H21	0.9300
C15—H15	0.9300	C22—C24	1.490 (3)
C14—C13	1.488 (3)	C22—C23	1.504 (3)
C13—H13B	0.9700	C24—H24C	0.9600
C13—H13A	0.9700	C24—H24A	0.9600
C11—C3	1.483 (3)	C24—H24B	0.9600
C11—C12	1.495 (3)	C23—H23B	0.9600
C12—H12C	0.9600	C23—H23C	0.9600
C12—H12A	0.9600	C23—H23A	0.9600
C12—H12B	0.9600

C11—N1—O3	111.18 (16)	O1—C9—C10	120.44 (16)
N1—O3—C13	108.13 (15)	C8—C9—C10	123.15 (18)
C9—O1—C2	123.03 (15)	C3—C4—C10	122.46 (18)
C7—O4—C20	117.49 (15)	C3—C4—H4	118.8
C18—C19—C14	121.5 (2)	C10—C4—H4	118.8
C18—C19—H19	119.2	C9—C10—C5	117.12 (17)
C14—C19—H19	119.2	C9—C10—C4	117.73 (18)
C17—C18—C19	120.6 (3)	C5—C10—C4	125.15 (18)
C17—C18—H18	119.7	C6—C5—C10	121.29 (19)
C19—C18—H18	119.7	C6—C5—H5	119.4
C18—C17—C16	120.4 (2)	C10—C5—H5	119.4
C18—C17—H17	119.8	C5—C6—C7	119.89 (19)
C16—C17—H17	119.8	C5—C6—H6	120.1
C17—C16—C15	119.2 (2)	C7—C6—H6	120.1
C17—C16—H16	120.4	C7—C8—C9	118.06 (18)
C15—C16—H16	120.4	C7—C8—H8	121.0
C14—C15—C16	120.1 (2)	C9—C8—H8	121.0
C14—C15—H15	119.9	O4—C7—C8	124.63 (18)
C16—C15—H15	119.9	O4—C7—C6	114.90 (17)
C15—C14—C19	118.1 (2)	C8—C7—C6	120.47 (18)
C15—C14—C13	121.5 (2)	O4—C20—C21	107.58 (17)
C19—C14—C13	120.3 (2)	O4—C20—H20B	110.2
O3—C13—C14	108.12 (18)	C21—C20—H20B	110.2
O3—C13—H13B	110.1	O4—C20—H20A	110.2
C14—C13—H13B	110.1	C21—C20—H20A	110.2
O3—C13—H13A	110.1	H20B—C20—H20A	108.5
C14—C13—H13A	110.1	C22—C21—C20	127.4 (2)
H13B—C13—H13A	108.4	C22—C21—H21	116.3
N1—C11—C3	113.69 (18)	C20—C21—H21	116.3
N1—C11—C12	124.18 (19)	C21—C22—C24	124.4 (2)
C3—C11—C12	122.1 (2)	C21—C22—C23	121.23 (19)
C11—C12—H12C	109.5	C24—C22—C23	114.42 (18)
C11—C12—H12A	109.5	C22—C24—H24C	109.5
H12C—C12—H12A	109.5	C22—C24—H24A	109.5
C11—C12—H12B	109.5	H24C—C24—H24A	109.5
H12C—C12—H12B	109.5	C22—C24—H24B	109.5
H12A—C12—H12B	109.5	H24C—C24—H24B	109.5
C4—C3—C2	118.98 (17)	H24A—C24—H24B	109.5
C4—C3—C11	122.25 (18)	C22—C23—H23B	109.5
C2—C3—C11	118.75 (17)	C22—C23—H23C	109.5
O2—C2—O1	116.02 (17)	H23B—C23—H23C	109.5
O2—C2—C3	126.66 (18)	C22—C23—H23A	109.5
O1—C2—C3	117.31 (17)	H23B—C23—H23A	109.5
O1—C9—C8	116.41 (16)	H23C—C23—H23A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2ⁱ	0.93	2.43	3.338 (3)	167

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₃NO₄
M_r	377.42
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.3038 (19), 11.467 (3), 12.184 (3)
α, β, γ (°)	92.368 (3), 92.067 (3), 102.340 (3)
V (Å³)	995.0 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.978, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	5604, 3912, 2341
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.155, 1.01
No. of reflections	3912
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2ⁱ	0.93	2.43	3.338 (3)	167

Symmetry code: (i) −x, −y, −z+1.

Acknowledgements

We are grateful to the Science and Technology Plan Project of Guangdong Province (No. 2008B010600008) for financial support.

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, H. Y., Gao, S. & Xi, Z. (2009). Inorg. Chem. Commun. 12, 300–303. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 6| June 2011| Page o1516

doi:10.1107/S1600536811019015

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-[(E)-1-(Benzyl­oxyimino)­eth­yl]-7-(3-methyl­but-2-en­yl­oxy)-2H-chromen-2-one

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Experimental

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Data collection

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organic compounds

3-[(E)-1-(Benzyloxyimino)ethyl]-7-(3-methylbut-2-enyloxy)-2H-chromen-2-one