3-(3,4-Dimeth­oxy­phen­yl)-4-(2-meth­oxy­anilino)furan-2(5H)-one

Tian, C.-L.; Tian, Q.

doi:10.1107/S1600536811031266

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2328

doi:10.1107/S1600536811031266

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3-(3,4-Dimethoxyphenyl)-4-(2-methoxyanilino)furan-2(5H)-one

Chun-Lian Tian ^a ^* and Qijian Tian ^b

^aKey Laboratory of Hunan Forest Product and Chemical Industry Engineering, Jishou University, Zhangjiajie 427000, People's Republic of China, and ^bKey Laboratory of Plant Resources Conservation and Utilization of Hunan Province, Jishou University, Jishou 416000, People's Republic of China
^*Correspondence e-mail: tianchunlian1970@163.com

(Received 28 July 2011; accepted 2 August 2011; online 11 August 2011)

In the title compound, C₁₉H₁₉NO₅, the furanone unit makes a dihedral angle of 30.93 (6)° with the benzene ring and a dihedral angle of 9.51 (6)° with the aniline ring. In the crystal, intermolecular C—H⋯O hydrogen bonds and C—H⋯π contacts link the molecules into sheets. A weak intramolecular hydrogen bond is also observed.

Related literature

For the biological activity of furan-2(5H)-one derivatives, see: Xiao, He et al. (2011 ). For related structures, see: Xiao et al. (2010 ); Xiao, Peng et al. (2011 ).

Experimental

Crystal data

C₁₉H₁₉NO₅
M_r = 341.35
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.4932 (5) Å
b = 11.5862 (7) Å
c = 18.5744 (12) Å
V = 1612.59 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.970, T_max = 0.980
10601 measured reflections
3940 independent reflections
3732 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.121
S = 1.09
3940 reflections
233 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.43	3.006 (2)	121
C17—H17B⋯O1ⁱ	0.96	2.58	3.428 (2)	147
C17—H17C⋯Cgⁱⁱ	0.96	2.94	3.847 (2)	158
C19—H19C⋯Cgⁱⁱⁱ	0.96	2.77	3.695 (2)	162
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536811031266/pv2437sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031266/pv2437Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031266/pv2437Isup3.cml

checkCIF report

Comment top

Furan-2(5H)-one is a part of many natural and synthetic compounds, which possess useful biological activities (Xiao, He et al., 2011). Herein, we reported the crystal structure of the title compound which is a derivatives of furan-2(5H)-one.

In the title molecule (Fig. 1), the bond distance C7—C10 (1.358 (2) Å) is indicative of a double bond which is consistent with the corresponding bond distances in the analogues of the title compound reported recently (Xiao et al., 2010; Xiao, Peng et al., 2011). The bond distance C10—N1 (1.359 (2) Å) is shorter than the standard C—N single bond (1.48 Å), but longer than a C═N double bond (1.28 Å). This clearly indicated that a p orbital of N1 is conjugated with the π molecular orbital of C7═C10 double bond. Moreover, 3,4-dimethoxybenzene moiety and aniline ring form dihedral angles of 30.93 (6) ° and 9.51 (6) ° with the central furan-2(5H)-one ring, respectively.

The molecules of the title compound are connected by intermolecular C17—H17B···O1 hydrogen bonds and C—H···π interactions to generate two-dimensional sheets of molecules (Tab. 1 & Fig. 2).

Related literature top

For the biological activity of furan-2(5H)-one derivatives, see: Xiao, He et al. (2011). For related structures, see: Xiao et al. (2010); Xiao, Peng et al. (2011).

Experimental top

To a mixture of 2-methoxyaniline (147 mg, 1.2 mmol) and p-toluene sulphonic acid (6.8 mg, 0.04 mmol) waqs added 3-(3,4-dimethoxyphenyl)-4-hydroxyfuran-2(5H)-one (236 mg, 1 mmol) which was prepared according to the procedure described earlier (Xiao, He et al., 2011). The mixture was heated to 370 K for 20 min. and toluene (12 ml) was then added and refluxed for 8 h. After toluene was removed under reduced pressure, the residue was purified by column chromatography on silica gel, eluting with EtOAc/petroleum ether (1:1). The crystals of the title compound were grown from EtOAc/petroleum ether (1:1) at room temperature by slow evaporation.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. Molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound viewed along the c axis, showing intermolecular C—H···O hydrogen bonds and C—H···π contacts. For the sake of clarity, the H atoms not involved in the hydrogen bonds have been omitted.

3-(3,4-Dimethoxyphenyl)-4-(2-methoxyanilino)furan-2(5H)-one top

Crystal data top

C₁₉H₁₉NO₅	F(000) = 720
M_r = 341.35	D_x = 1.406 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3629 reflections
a = 7.4932 (5) Å	θ = 2.4–27.8°
b = 11.5862 (7) Å	µ = 0.10 mm⁻¹
c = 18.5744 (12) Å	T = 298 K
V = 1612.59 (18) Å³	Block, colorless
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3940 independent reflections
Radiation source: fine-focus sealed tube	3732 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.970, T_max = 0.980	k = −14→15
10601 measured reflections	l = −19→24

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0689P)² + 0.1364P] where P = (F_o² + 2F_c²)/3
3940 reflections	(Δ/σ)_max = 0.001
233 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₉H₁₉NO₅	V = 1612.59 (18) Å³
M_r = 341.35	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.4932 (5) Å	µ = 0.10 mm⁻¹
b = 11.5862 (7) Å	T = 298 K
c = 18.5744 (12) Å	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3940 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3732 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.980	R_int = 0.046
10601 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.24 e Å⁻³
3940 reflections	Δρ_min = −0.34 e Å⁻³
233 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	0.1004 (2)	0.78788 (13)	0.96299 (8)	0.0298 (3)
C2	0.1438 (2)	0.90439 (13)	0.96587 (9)	0.0357 (3)
H2	0.1580	0.9453	0.9232	0.043*
C3	0.1665 (2)	0.96090 (14)	1.03105 (10)	0.0386 (4)
H3	0.1968	1.0387	1.0314	0.046*
C4	0.1447 (2)	0.90327 (15)	1.09529 (9)	0.0380 (4)
C5	0.0948 (2)	0.78615 (14)	1.09393 (9)	0.0354 (3)
C6	0.0722 (2)	0.73015 (13)	1.02868 (8)	0.0325 (3)
H6	0.0379	0.6530	1.0283	0.039*
C7	0.0929 (2)	0.72736 (13)	0.89352 (8)	0.0306 (3)
C8	0.0519 (2)	0.78617 (14)	0.82608 (9)	0.0375 (4)
C9	0.1286 (3)	0.60193 (14)	0.79642 (8)	0.0410 (4)
H9A	0.2447	0.5807	0.7774	0.049*
H9B	0.0429	0.5428	0.7833	0.049*
C10	0.1364 (2)	0.61684 (14)	0.87662 (8)	0.0313 (3)
C11	0.2423 (2)	0.41733 (13)	0.91057 (9)	0.0327 (3)
C12	0.3074 (2)	0.35932 (13)	0.97200 (9)	0.0337 (3)
C13	0.3749 (2)	0.24856 (14)	0.96556 (10)	0.0423 (4)
H13	0.4209	0.2110	1.0057	0.051*
C14	0.3739 (3)	0.19349 (15)	0.89930 (12)	0.0478 (4)
H14	0.4209	0.1195	0.8951	0.057*
C15	0.3044 (3)	0.24702 (15)	0.84022 (11)	0.0452 (4)
H15	0.3022	0.2087	0.7962	0.054*
C16	0.2368 (2)	0.35889 (15)	0.84532 (9)	0.0401 (4)
H16	0.1880	0.3944	0.8050	0.048*
C17	0.3697 (3)	0.37008 (17)	1.09825 (10)	0.0503 (5)
H17A	0.2980	0.3053	1.1125	0.075*
H17B	0.3706	0.4264	1.1362	0.075*
H17C	0.4895	0.3447	1.0890	0.075*
C18	0.0450 (3)	0.61586 (16)	1.16219 (10)	0.0514 (5)
H18A	−0.0672	0.5970	1.1402	0.077*
H18B	0.0447	0.5905	1.2114	0.077*
H18C	0.1398	0.5780	1.1366	0.077*
C19	0.2239 (3)	1.06783 (16)	1.16409 (12)	0.0539 (5)
H19A	0.3331	1.0760	1.1375	0.081*
H19B	0.2431	1.0908	1.2131	0.081*
H19C	0.1336	1.1158	1.1429	0.081*
H1	0.210 (3)	0.5550 (18)	0.9629 (12)	0.046 (6)*
N1	0.1861 (2)	0.53176 (12)	0.92278 (7)	0.0360 (3)
O1	0.0054 (2)	0.88447 (10)	0.81447 (7)	0.0520 (4)
O2	0.0742 (2)	0.71219 (10)	0.76969 (6)	0.0484 (3)
O3	0.29681 (17)	0.42052 (10)	1.03438 (6)	0.0398 (3)
O4	0.0713 (2)	0.73683 (11)	1.15974 (7)	0.0529 (4)
O5	0.1675 (2)	0.95037 (11)	1.16213 (7)	0.0532 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0314 (7)	0.0298 (7)	0.0282 (7)	0.0035 (5)	0.0000 (5)	0.0007 (6)
C2	0.0432 (8)	0.0308 (7)	0.0331 (7)	0.0034 (6)	0.0009 (7)	0.0070 (6)
C3	0.0450 (9)	0.0253 (7)	0.0456 (9)	0.0010 (6)	−0.0016 (8)	−0.0022 (6)
C4	0.0433 (9)	0.0358 (8)	0.0349 (8)	0.0017 (7)	−0.0039 (7)	−0.0054 (7)
C5	0.0440 (9)	0.0337 (7)	0.0284 (7)	−0.0004 (7)	−0.0007 (6)	0.0006 (6)
C6	0.0395 (8)	0.0287 (7)	0.0292 (7)	−0.0005 (6)	−0.0007 (6)	0.0010 (6)
C7	0.0365 (8)	0.0314 (7)	0.0240 (7)	0.0013 (6)	−0.0001 (5)	0.0044 (5)
C8	0.0483 (9)	0.0369 (8)	0.0272 (7)	0.0023 (7)	−0.0013 (6)	0.0050 (6)
C9	0.0625 (10)	0.0341 (8)	0.0264 (7)	0.0028 (8)	−0.0008 (7)	0.0022 (6)
C10	0.0357 (7)	0.0334 (7)	0.0248 (7)	−0.0007 (6)	−0.0003 (5)	0.0020 (6)
C11	0.0332 (7)	0.0292 (7)	0.0359 (8)	0.0002 (6)	0.0017 (6)	0.0016 (6)
C12	0.0348 (7)	0.0299 (7)	0.0365 (8)	−0.0035 (6)	−0.0008 (6)	0.0037 (6)
C13	0.0447 (9)	0.0294 (8)	0.0528 (10)	0.0015 (7)	−0.0034 (8)	0.0102 (7)
C14	0.0501 (10)	0.0269 (7)	0.0664 (12)	0.0017 (7)	0.0047 (9)	−0.0025 (8)
C15	0.0519 (10)	0.0340 (8)	0.0496 (10)	−0.0034 (8)	0.0080 (8)	−0.0089 (8)
C16	0.0472 (9)	0.0360 (8)	0.0369 (9)	−0.0010 (7)	−0.0001 (7)	−0.0015 (7)
C17	0.0676 (12)	0.0442 (10)	0.0392 (9)	−0.0006 (9)	−0.0172 (9)	0.0095 (7)
C18	0.0718 (13)	0.0466 (10)	0.0357 (9)	−0.0087 (9)	−0.0026 (9)	0.0116 (8)
C19	0.0584 (12)	0.0448 (10)	0.0586 (12)	−0.0023 (9)	−0.0102 (10)	−0.0203 (9)
N1	0.0534 (9)	0.0302 (6)	0.0245 (6)	0.0080 (6)	−0.0046 (6)	−0.0010 (5)
O1	0.0830 (10)	0.0373 (6)	0.0358 (7)	0.0139 (7)	−0.0052 (6)	0.0104 (5)
O2	0.0808 (10)	0.0388 (6)	0.0256 (5)	0.0069 (6)	−0.0025 (6)	0.0060 (5)
O3	0.0528 (7)	0.0350 (6)	0.0315 (6)	0.0025 (5)	−0.0074 (5)	0.0055 (4)
O4	0.0895 (10)	0.0430 (7)	0.0262 (6)	−0.0069 (7)	−0.0014 (6)	−0.0004 (5)
O5	0.0796 (10)	0.0422 (7)	0.0378 (7)	−0.0057 (6)	−0.0079 (7)	−0.0112 (5)

Geometric parameters (Å, º) top

C1—C2	1.390 (2)	C11—C12	1.411 (2)
C1—C6	1.407 (2)	C12—O3	1.3607 (19)
C1—C7	1.470 (2)	C12—C13	1.384 (2)
C2—C3	1.387 (2)	C13—C14	1.386 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.377 (2)	C14—C15	1.364 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—O5	1.367 (2)	C15—C16	1.395 (2)
C4—C5	1.408 (2)	C15—H15	0.9300
C5—O4	1.361 (2)	C16—H16	0.9300
C5—C6	1.385 (2)	C17—O3	1.431 (2)
C6—H6	0.9300	C17—H17A	0.9600
C7—C10	1.358 (2)	C17—H17B	0.9600
C7—C8	1.459 (2)	C17—H17C	0.9600
C8—O1	1.210 (2)	C18—O4	1.416 (2)
C8—O2	1.364 (2)	C18—H18A	0.9600
C9—O2	1.4299 (19)	C18—H18B	0.9600
C9—C10	1.501 (2)	C18—H18C	0.9600
C9—H9A	0.9700	C19—O5	1.425 (2)
C9—H9B	0.9700	C19—H19A	0.9600
C10—N1	1.359 (2)	C19—H19B	0.9600
C11—C16	1.389 (2)	C19—H19C	0.9600
C11—N1	1.4093 (19)	N1—H1	0.81 (2)

C2—C1—C6	117.60 (13)	C13—C12—C11	119.85 (15)
C2—C1—C7	120.42 (13)	C12—C13—C14	120.10 (16)
C6—C1—C7	121.92 (13)	C12—C13—H13	120.0
C3—C2—C1	121.40 (14)	C14—C13—H13	120.0
C3—C2—H2	119.3	C15—C14—C13	120.47 (16)
C1—C2—H2	119.3	C15—C14—H14	119.8
C4—C3—C2	120.86 (14)	C13—C14—H14	119.8
C4—C3—H3	119.6	C14—C15—C16	120.44 (17)
C2—C3—H3	119.6	C14—C15—H15	119.8
O5—C4—C3	125.35 (15)	C16—C15—H15	119.8
O5—C4—C5	115.74 (15)	C11—C16—C15	120.10 (16)
C3—C4—C5	118.91 (14)	C11—C16—H16	119.9
O4—C5—C6	125.00 (14)	C15—C16—H16	119.9
O4—C5—C4	115.02 (14)	O3—C17—H17A	109.5
C6—C5—C4	119.98 (14)	O3—C17—H17B	109.5
C5—C6—C1	121.18 (14)	H17A—C17—H17B	109.5
C5—C6—H6	119.4	O3—C17—H17C	109.5
C1—C6—H6	119.4	H17A—C17—H17C	109.5
C10—C7—C8	107.00 (13)	H17B—C17—H17C	109.5
C10—C7—C1	130.07 (13)	O4—C18—H18A	109.5
C8—C7—C1	122.63 (14)	O4—C18—H18B	109.5
O1—C8—O2	119.34 (14)	H18A—C18—H18B	109.5
O1—C8—C7	130.77 (16)	O4—C18—H18C	109.5
O2—C8—C7	109.89 (13)	H18A—C18—H18C	109.5
O2—C9—C10	104.64 (13)	H18B—C18—H18C	109.5
O2—C9—H9A	110.8	O5—C19—H19A	109.5
C10—C9—H9A	110.8	O5—C19—H19B	109.5
O2—C9—H9B	110.8	H19A—C19—H19B	109.5
C10—C9—H9B	110.8	O5—C19—H19C	109.5
H9A—C9—H9B	108.9	H19A—C19—H19C	109.5
C7—C10—N1	127.16 (14)	H19B—C19—H19C	109.5
C7—C10—C9	109.19 (13)	C10—N1—C11	131.53 (14)
N1—C10—C9	123.60 (15)	C10—N1—H1	113.5 (15)
C16—C11—N1	126.17 (15)	C11—N1—H1	113.1 (15)
C16—C11—C12	118.92 (14)	C8—O2—C9	109.26 (12)
N1—C11—C12	114.91 (14)	C12—O3—C17	118.09 (13)
O3—C12—C13	125.31 (14)	C5—O4—C18	117.54 (14)
O3—C12—C11	114.83 (13)	C4—O5—C19	116.20 (15)

C6—C1—C2—C3	2.8 (2)	O2—C9—C10—N1	−178.82 (16)
C7—C1—C2—C3	−174.47 (14)	C16—C11—C12—O3	−175.81 (14)
C1—C2—C3—C4	−0.7 (2)	N1—C11—C12—O3	3.5 (2)
C2—C3—C4—O5	178.57 (16)	C16—C11—C12—C13	4.0 (2)
C2—C3—C4—C5	−1.4 (2)	N1—C11—C12—C13	−176.63 (15)
O5—C4—C5—O4	1.8 (2)	O3—C12—C13—C14	178.05 (16)
C3—C4—C5—O4	−178.21 (16)	C11—C12—C13—C14	−1.8 (3)
O5—C4—C5—C6	−178.62 (15)	C12—C13—C14—C15	−0.9 (3)
C3—C4—C5—C6	1.4 (2)	C13—C14—C15—C16	1.3 (3)
O4—C5—C6—C1	−179.67 (16)	N1—C11—C16—C15	177.11 (17)
C4—C5—C6—C1	0.8 (2)	C12—C11—C16—C15	−3.6 (2)
C2—C1—C6—C5	−2.8 (2)	C14—C15—C16—C11	1.0 (3)
C7—C1—C6—C5	174.39 (15)	C7—C10—N1—C11	−176.24 (17)
C2—C1—C7—C10	145.33 (17)	C9—C10—N1—C11	1.2 (3)
C6—C1—C7—C10	−31.8 (3)	C16—C11—N1—C10	−9.3 (3)
C2—C1—C7—C8	−27.5 (2)	C12—C11—N1—C10	171.42 (17)
C6—C1—C7—C8	155.39 (16)	O1—C8—O2—C9	−179.88 (18)
C10—C7—C8—O1	179.3 (2)	C7—C8—O2—C9	0.6 (2)
C1—C7—C8—O1	−6.4 (3)	C10—C9—O2—C8	0.2 (2)
C10—C7—C8—O2	−1.2 (2)	C13—C12—O3—C17	3.7 (2)
C1—C7—C8—O2	173.04 (15)	C11—C12—O3—C17	−176.45 (15)
C8—C7—C10—N1	179.05 (16)	C6—C5—O4—C18	8.8 (3)
C1—C7—C10—N1	5.4 (3)	C4—C5—O4—C18	−171.59 (17)
C8—C7—C10—C9	1.34 (19)	C3—C4—O5—C19	−2.1 (3)
C1—C7—C10—C9	−172.34 (16)	C5—C4—O5—C19	177.94 (16)
O2—C9—C10—C7	−1.0 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.43	3.006 (2)	121
C17—H17B···O1ⁱ	0.96	2.58	3.428 (2)	147
C17—H17C···Cgⁱⁱ	0.96	2.94	3.847 (2)	158
C19—H19C···Cgⁱⁱⁱ	0.96	2.77	3.695 (2)	162

Symmetry codes: (i) x+1/2, −y+3/2, −z+2; (ii) x+1/2, −y+1/2, −z+2; (iii) x−1/2, −y+3/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉NO₅
M_r	341.35
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.4932 (5), 11.5862 (7), 18.5744 (12)
V (Å³)	1612.59 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.970, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	10601, 3940, 3732
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.121, 1.09
No. of reflections	3940
No. of parameters	233
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.34

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.43	3.006 (2)	120.5
C17—H17B···O1ⁱ	0.96	2.58	3.428 (2)	147.1
C17—H17C···Cgⁱⁱ	0.96	2.94	3.847 (2)	158
C19—H19C···Cgⁱⁱⁱ	0.96	2.77	3.695 (2)	162

Symmetry codes: (i) x+1/2, −y+3/2, −z+2; (ii) x+1/2, −y+1/2, −z+2; (iii) x−1/2, −y+3/2, −z+2.

Acknowledgements

This work was financed by a project supported by the Science and Technology Planning Project of Hunan Province, China (Nos. 2010TP4007–1 and 2010TC2002) and by an aid program for the Science and Technology Innovative Research Team (Chemicals of Forestry Resources and Development of Forest Products) in Higher Educational Institutions of Hunan Province.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xiao, Z.-P., He, X.-B., Peng, Z.-Y., Xiong, T.-J., Peng, J. & Chen, L.-H. (2011). Bioorg. Med. Chem. 19, 1571–1579. CrossRef CAS Google Scholar
Xiao, Z.-P., Peng, Z.-Y., Liu, Z.-X., Chen, L.-H. & Zhu, H.-L. (2011). J. Chem. Crystallogr. 41, 649–653. CrossRef CAS Google Scholar
Xiao, Z.-P., Zhu, J., Jiang, W., Li, G.-X. & Wang, X.-D. (2010). Z. Kristallogr. New Cryst. Struct. 225, 797–798. CAS Google Scholar

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Volume 67| Part 9| September 2011| Page o2328

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