1,3-Bis(4-methyl­benz­yl)pyrimidine-2,4(1H,3H)-dione

Li, G.-C.; Song, X.-P.; Zhang, L.-K.; Cui, J.-J.; Yang, F.-L.

doi:10.1107/S1600536809053586

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o193

doi:10.1107/S1600536809053586

Open

access

1,3-Bis(4-methylbenzyl)pyrimidine-2,4(1H,3H)-dione

Gong-Chun Li,^a Xiao-Ping Song,^a Li-Ke Zhang,^a Jiao-Jiao Cui ^a and Feng-Ling Yang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China
^*Correspondence e-mail: actaeli@gmail.com

(Received 1 December 2009; accepted 12 December 2009; online 19 December 2009)

In the title molecule, C₂₀H₂₀N₂O₂, the central pyrimidine ring forms dihedral angles of 71.9 (1) and 69.8 (1)° with the two benzene rings. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link molecules into centrosymmetric dimers. The crystal packing exhibits also π–π interactions as indicated by short distances of 3.674 (2) Å between the centroids of the pyrimidine rings of neighbouring molecules.

Related literature

For the crystal structure of 1,3-bis(4-chlorobenzyl)pyrimidine-2,4(1H,3H)-dione, see: Yang & Li (2006 ).

Experimental

Crystal data

C₂₀H₂₀N₂O₂
M_r = 320.38
Triclinic, $[P \overline 1]$
a = 9.4182 (19) Å
b = 10.102 (2) Å
c = 10.448 (2) Å
α = 66.25 (3)°
β = 80.79 (3)°
γ = 71.18 (3)°
V = 860.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ) T_min = 0.984, T_max = 0.984
8622 measured reflections
3001 independent reflections
2529 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.088
wR(F²) = 0.161
S = 1.27
3001 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2ⁱ	0.93	2.50	3.430 (4)	174
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: CrystalClear (Rigaku/MSC, 2006); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053586/cv2673sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053586/cv2673Isup2.hkl

checkCIF report

Comment top

In continuation of our search for new biologically active pyrimidine derivatives (Yang & Li, 2006), we present here the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related 1,3-bis(4-chlorobenzyl)pyrimidine-2,4(1H,3H)-dione (Yang & Li, 2006). The central pyrimidine ring forms dihedral angles of 71.9 (1)° and 69.8 (1)° with the two benzene rings, respectively. Weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into centrosymmetric dimers. The crystal packing exhibits also π-π interactions proved by short distances of 3.674 (2) Å between the centroids of pyrimidine rings from the neighbouring molecules.

Related literature top

For the crystal structure of 1,3-bis(4-chlorobenzyl)pyrimidine-2,4(1H,3H)-dione, see: Yang & Li (2006).

Experimental top

Uracil (0.56 g, 5 mmol) and anhydrous potassium carbonate (0.84 g, 6 mmol) were mixed in N,N-dimethylformamide (20 ml). A solution of 4-methyl-benzyl chloride (0.70 g, 5 mmol) in acetone (10 ml) was then added dropwise, with stirring, at room temperature, and the mixture was stirred for another 10 h and then refluxed for 4 h. The solvent was evaporated in vacuo and the residue was washed with water. The resulting white precipitate was filtered off and purified by column chromatography on silica gel (petroleum ether:ethyl acetate = 2:1). The title compound was recrystallized from ethanol and single crystals of (I) were obtained by slow evaporation.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); 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. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms omitted for clarity.

1,3-Bis(4-methylbenzyl)pyrimidine-2,4(1H,3H)-dione top

Crystal data top

C₂₀H₂₀N₂O₂	Z = 2
M_r = 320.38	F(000) = 340
Triclinic, P1	D_x = 1.236 Mg m⁻³
a = 9.4182 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.102 (2) Å	Cell parameters from 2459 reflections
c = 10.448 (2) Å	θ = 2.1–27.9°
α = 66.25 (3)°	µ = 0.08 mm⁻¹
β = 80.79 (3)°	T = 293 K
γ = 71.18 (3)°	Prism, colourless
V = 860.7 (3) Å³	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3001 independent reflections
Radiation source: fine-focus sealed tube	2529 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
phi and ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −11→12
T_min = 0.984, T_max = 0.984	l = −12→12
8622 measured reflections

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)] = 0.088	H-atom parameters constrained
wR(F²) = 0.161	w = 1/[σ²(F_o²) + (0.0409P)² + 0.3734P] where P = (F_o² + 2F_c²)/3
S = 1.27	(Δ/σ)_max < 0.001
3001 reflections	Δρ_max = 0.14 e Å⁻³
219 parameters	Δρ_min = −0.17 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₀H₂₀N₂O₂	γ = 71.18 (3)°
M_r = 320.38	V = 860.7 (3) Å³
Triclinic, P1	Z = 2
a = 9.4182 (19) Å	Mo Kα radiation
b = 10.102 (2) Å	µ = 0.08 mm⁻¹
c = 10.448 (2) Å	T = 293 K
α = 66.25 (3)°	0.20 × 0.20 × 0.20 mm
β = 80.79 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3001 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	2529 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.984	R_int = 0.034
8622 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.088	219 parameters
wR(F²) = 0.161	H-atom parameters constrained
S = 1.27	Δρ_max = 0.14 e Å⁻³
3001 reflections	Δρ_min = −0.17 e Å⁻³

Special details top

Experimental. Software + citation

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	0.4982 (3)	0.1871 (3)	0.6026 (3)	0.0711 (7)
O2	0.3392 (2)	0.4909 (3)	0.8542 (2)	0.0661 (7)
N1	0.4156 (2)	0.3369 (3)	0.7299 (2)	0.0452 (6)
N2	0.2678 (3)	0.5867 (3)	0.6284 (3)	0.0491 (6)
C1	0.3407 (3)	0.4728 (3)	0.7458 (3)	0.0483 (7)
C2	0.6580 (3)	0.1972 (3)	0.8500 (3)	0.0431 (7)
C3	0.1828 (3)	0.7346 (3)	0.6372 (4)	0.0596 (9)
H3A	0.1960	0.8147	0.5494	0.072*
H3B	0.2227	0.7467	0.7105	0.072*
C4	0.3402 (3)	0.4340 (4)	0.4937 (3)	0.0562 (8)
H4	0.3370	0.4235	0.4099	0.067*
C5	0.2677 (3)	0.5635 (4)	0.5079 (3)	0.0543 (8)
H5	0.2143	0.6422	0.4330	0.065*
C6	0.7652 (3)	0.0843 (3)	0.8165 (3)	0.0529 (8)
H6	0.7358	0.0149	0.7973	0.064*
C7	0.4931 (3)	0.2105 (3)	0.8525 (3)	0.0521 (8)
H7A	0.4827	0.1170	0.8550	0.063*
H7B	0.4451	0.2249	0.9372	0.063*
C8	−0.2911 (3)	0.7765 (3)	0.7206 (3)	0.0492 (8)
C9	0.4242 (3)	0.3092 (4)	0.6070 (3)	0.0526 (8)
C10	−0.0848 (4)	0.8346 (4)	0.5629 (3)	0.0577 (8)
H10	−0.0510	0.8844	0.4730	0.069*
C11	0.0171 (3)	0.7490 (3)	0.6673 (3)	0.0473 (7)
C12	0.9150 (4)	0.0739 (4)	0.8113 (3)	0.0614 (9)
H12	0.9854	−0.0040	0.7901	0.074*
C13	−0.0374 (4)	0.6768 (4)	0.7999 (3)	0.0599 (9)
H13	0.0286	0.6189	0.8726	0.072*
C14	−0.1891 (4)	0.6899 (3)	0.8254 (3)	0.0582 (9)
H14	−0.2231	0.6392	0.9150	0.070*
C15	0.9639 (4)	0.1749 (4)	0.8365 (3)	0.0630 (10)
C16	−0.4572 (3)	0.7930 (4)	0.7502 (4)	0.0696 (10)
H16A	−0.5029	0.8770	0.7787	0.104*
H16B	−0.4712	0.7025	0.8235	0.104*
H16C	−0.5030	0.8099	0.6671	0.104*
C17	0.7049 (4)	0.2967 (4)	0.8803 (3)	0.0601 (9)
H17	0.6349	0.3714	0.9064	0.072*
C18	−0.2361 (4)	0.8480 (4)	0.5894 (4)	0.0610 (9)
H18	−0.3022	0.9066	0.5168	0.073*
C19	0.8569 (4)	0.2856 (4)	0.8720 (4)	0.0717 (11)
H19	0.8869	0.3548	0.8909	0.086*
C20	1.1291 (4)	0.1673 (6)	0.8239 (4)	0.1041 (16)
H20A	1.1884	0.0636	0.8601	0.156*
H20B	1.1462	0.2195	0.8764	0.156*
H20C	1.1572	0.2137	0.7274	0.156*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0713 (16)	0.0577 (15)	0.0837 (18)	−0.0011 (12)	−0.0192 (13)	−0.0334 (13)
O2	0.0646 (15)	0.0773 (16)	0.0552 (14)	−0.0105 (12)	−0.0044 (11)	−0.0303 (13)
N1	0.0379 (13)	0.0480 (15)	0.0434 (14)	−0.0112 (11)	−0.0041 (11)	−0.0106 (12)
N2	0.0424 (14)	0.0438 (14)	0.0534 (16)	−0.0082 (11)	−0.0015 (12)	−0.0138 (12)
C1	0.0381 (17)	0.0513 (19)	0.052 (2)	−0.0148 (14)	0.0023 (14)	−0.0162 (16)
C2	0.0462 (17)	0.0411 (16)	0.0355 (15)	−0.0103 (14)	−0.0092 (13)	−0.0066 (13)
C3	0.0519 (19)	0.0480 (19)	0.076 (2)	−0.0136 (16)	0.0004 (16)	−0.0216 (17)
C4	0.053 (2)	0.057 (2)	0.058 (2)	−0.0112 (17)	−0.0080 (16)	−0.0218 (17)
C5	0.0481 (19)	0.058 (2)	0.0452 (19)	−0.0149 (16)	−0.0077 (14)	−0.0052 (16)
C6	0.055 (2)	0.0476 (18)	0.0524 (19)	−0.0145 (15)	−0.0082 (15)	−0.0126 (15)
C7	0.0487 (18)	0.0488 (18)	0.0469 (18)	−0.0157 (15)	−0.0059 (14)	−0.0032 (14)
C8	0.0509 (19)	0.0464 (18)	0.0543 (19)	−0.0124 (15)	0.0041 (15)	−0.0262 (15)
C9	0.0415 (18)	0.054 (2)	0.062 (2)	−0.0143 (16)	−0.0056 (15)	−0.0203 (17)
C10	0.059 (2)	0.056 (2)	0.0474 (19)	−0.0160 (16)	0.0000 (15)	−0.0094 (16)
C11	0.0463 (17)	0.0376 (16)	0.0568 (19)	−0.0090 (14)	−0.0008 (15)	−0.0192 (14)
C12	0.052 (2)	0.060 (2)	0.054 (2)	−0.0038 (17)	−0.0051 (16)	−0.0103 (17)
C13	0.056 (2)	0.060 (2)	0.0489 (19)	−0.0025 (16)	−0.0081 (16)	−0.0143 (16)
C14	0.060 (2)	0.054 (2)	0.0499 (19)	−0.0094 (17)	0.0092 (16)	−0.0181 (16)
C15	0.050 (2)	0.073 (2)	0.047 (2)	−0.0214 (19)	−0.0100 (15)	0.0015 (17)
C16	0.053 (2)	0.081 (3)	0.083 (3)	−0.0202 (18)	0.0078 (18)	−0.042 (2)
C17	0.058 (2)	0.056 (2)	0.068 (2)	−0.0105 (17)	−0.0118 (17)	−0.0254 (17)
C18	0.051 (2)	0.070 (2)	0.057 (2)	−0.0112 (17)	−0.0121 (16)	−0.0191 (18)
C19	0.075 (3)	0.072 (2)	0.079 (3)	−0.034 (2)	−0.024 (2)	−0.021 (2)
C20	0.055 (2)	0.149 (4)	0.084 (3)	−0.042 (3)	−0.010 (2)	−0.007 (3)

Geometric parameters (Å, º) top

O1—C9	1.221 (4)	C8—C14	1.382 (4)
O2—C1	1.215 (3)	C8—C16	1.513 (4)
N1—C1	1.390 (4)	C10—C18	1.381 (4)
N1—C9	1.405 (4)	C10—C11	1.378 (4)
N1—C7	1.478 (3)	C10—H10	0.9300
N2—C5	1.370 (4)	C11—C13	1.383 (4)
N2—C1	1.386 (4)	C12—C15	1.371 (5)
N2—C3	1.482 (4)	C12—H12	0.9300
C2—C17	1.376 (4)	C13—C14	1.383 (4)
C2—C6	1.381 (4)	C13—H13	0.9300
C2—C7	1.512 (4)	C14—H14	0.9300
C3—C11	1.512 (4)	C15—C19	1.375 (5)
C3—H3A	0.9700	C15—C20	1.520 (4)
C3—H3B	0.9700	C16—H16A	0.9600
C4—C5	1.322 (4)	C16—H16B	0.9600
C4—C9	1.439 (4)	C16—H16C	0.9600
C4—H4	0.9300	C17—C19	1.391 (4)
C5—H5	0.9300	C17—H17	0.9300
C6—C12	1.375 (4)	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—H7A	0.9700	C20—H20A	0.9600
C7—H7B	0.9700	C20—H20B	0.9600
C8—C18	1.374 (4)	C20—H20C	0.9600

C1—N1—C9	125.6 (3)	C18—C10—C11	121.3 (3)
C1—N1—C7	117.3 (3)	C18—C10—H10	119.4
C9—N1—C7	117.1 (3)	C11—C10—H10	119.4
C5—N2—C1	121.7 (3)	C10—C11—C13	117.7 (3)
C5—N2—C3	119.8 (3)	C10—C11—C3	120.8 (3)
C1—N2—C3	118.5 (3)	C13—C11—C3	121.5 (3)
O2—C1—N2	122.4 (3)	C6—C12—C15	122.0 (3)
O2—C1—N1	122.7 (3)	C6—C12—H12	119.0
N2—C1—N1	114.9 (3)	C15—C12—H12	119.0
C17—C2—C6	118.5 (3)	C14—C13—C11	120.7 (3)
C17—C2—C7	121.2 (3)	C14—C13—H13	119.6
C6—C2—C7	120.3 (3)	C11—C13—H13	119.6
N2—C3—C11	111.9 (2)	C8—C14—C13	121.5 (3)
N2—C3—H3A	109.2	C8—C14—H14	119.3
C11—C3—H3A	109.2	C13—C14—H14	119.3
N2—C3—H3B	109.2	C12—C15—C19	117.3 (3)
C11—C3—H3B	109.2	C12—C15—C20	121.7 (4)
H3A—C3—H3B	107.9	C19—C15—C20	120.9 (4)
C5—C4—C9	120.5 (3)	C8—C16—H16A	109.5
C5—C4—H4	119.8	C8—C16—H16B	109.5
C9—C4—H4	119.8	H16A—C16—H16B	109.5
C4—C5—N2	122.8 (3)	C8—C16—H16C	109.5
C4—C5—H5	118.6	H16A—C16—H16C	109.5
N2—C5—H5	118.6	H16B—C16—H16C	109.5
C12—C6—C2	120.5 (3)	C2—C17—C19	120.1 (3)
C12—C6—H6	119.8	C2—C17—H17	120.0
C2—C6—H6	119.8	C19—C17—H17	120.0
N1—C7—C2	112.6 (2)	C10—C18—C8	121.4 (3)
N1—C7—H7A	109.1	C10—C18—H18	119.3
C2—C7—H7A	109.1	C8—C18—H18	119.3
N1—C7—H7B	109.1	C15—C19—C17	121.6 (3)
C2—C7—H7B	109.1	C15—C19—H19	119.2
H7A—C7—H7B	107.8	C17—C19—H19	119.2
C18—C8—C14	117.5 (3)	C15—C20—H20A	109.5
C18—C8—C16	121.4 (3)	C15—C20—H20B	109.5
C14—C8—C16	121.1 (3)	H20A—C20—H20B	109.5
O1—C9—N1	120.2 (3)	C15—C20—H20C	109.5
O1—C9—C4	125.3 (3)	H20A—C20—H20C	109.5
N1—C9—C4	114.4 (3)	H20B—C20—H20C	109.5

C5—N2—C1—O2	−178.4 (3)	C5—C4—C9—O1	−177.7 (3)
C3—N2—C1—O2	−1.2 (4)	C5—C4—C9—N1	2.5 (4)
C5—N2—C1—N1	1.6 (4)	C18—C10—C11—C13	−0.1 (5)
C3—N2—C1—N1	178.9 (2)	C18—C10—C11—C3	179.8 (3)
C9—N1—C1—O2	−178.8 (3)	N2—C3—C11—C10	−103.7 (3)
C7—N1—C1—O2	1.1 (4)	N2—C3—C11—C13	76.1 (4)
C9—N1—C1—N2	1.2 (4)	C2—C6—C12—C15	−1.1 (5)
C7—N1—C1—N2	−178.9 (2)	C10—C11—C13—C14	0.5 (5)
C5—N2—C3—C11	80.2 (3)	C3—C11—C13—C14	−179.3 (3)
C1—N2—C3—C11	−97.2 (3)	C18—C8—C14—C13	0.8 (5)
C9—C4—C5—N2	0.0 (5)	C16—C8—C14—C13	−178.6 (3)
C1—N2—C5—C4	−2.2 (4)	C11—C13—C14—C8	−0.9 (5)
C3—N2—C5—C4	−179.5 (3)	C6—C12—C15—C19	2.1 (5)
C17—C2—C6—C12	−1.1 (4)	C6—C12—C15—C20	−177.1 (3)
C7—C2—C6—C12	178.7 (3)	C6—C2—C17—C19	2.3 (5)
C1—N1—C7—C2	−95.8 (3)	C7—C2—C17—C19	−177.5 (3)
C9—N1—C7—C2	84.1 (3)	C11—C10—C18—C8	0.0 (5)
C17—C2—C7—N1	74.8 (4)	C14—C8—C18—C10	−0.3 (5)
C6—C2—C7—N1	−105.0 (3)	C16—C8—C18—C10	179.0 (3)
C1—N1—C9—O1	177.0 (3)	C12—C15—C19—C17	−0.9 (5)
C7—N1—C9—O1	−2.8 (4)	C20—C15—C19—C17	178.3 (3)
C1—N1—C9—C4	−3.2 (4)	C2—C17—C19—C15	−1.3 (5)
C7—N1—C9—C4	176.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ⁱ	0.93	2.50	3.430 (4)	174

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀N₂O₂
M_r	320.38
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.4182 (19), 10.102 (2), 10.448 (2)
α, β, γ (°)	66.25 (3), 80.79 (3), 71.18 (3)
V (Å³)	860.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2006)
T_min, T_max	0.984, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	8622, 3001, 2529
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.088, 0.161, 1.27
No. of reflections	3001
No. of parameters	219
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.17

Computer programs: CrystalClear (Rigaku/MSC, 2006), 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
C14—H14···O2ⁱ	0.93	2.50	3.430 (4)	174.3

Symmetry code: (i) −x, −y+1, −z+2.

Acknowledgements

This work was supported by the Natural Science Foundation of Henan Province, China (grant No. 082300420110) and the Natural Science Foundation of Henan Province Education Department, China (grant No. 2007150036).

References

Rigaku/MSC (2006). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, F.-L. & Li, G.-C. (2006). Acta Cryst. E62, o3405–o3406. Web of Science CSD CrossRef IUCr Journals Google Scholar