3-Phenyl-2-(prop-2-yn­yloxy)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one

Qu, Y.-N.; Pan, L.-R.; Hu, Y.-G.

doi:10.1107/S160053680706326X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o137

https://doi.org/10.1107/S160053680706326X

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3-Phenyl-2-(prop-2-ynyloxy)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one

Yong-Nian Qu,^a Long-Rui Pan ^b and Yang-Gen Hu ^a ^*

^aDepartment of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China, and ^bDepartment of Pharmacology, Yunyang Medical College, Shiyan 442000, People's Republic of China
^*Correspondence e-mail: huyangg111@yahoo.com.cn

(Received 25 November 2007; accepted 26 November 2007; online 6 December 2007)

In the title compound, C₁₉H₁₂N₂O₃, the 1-benzofuro[3,2-d]pyrimidinone unit is approximately planar, the maximum deviation from the mean plane being 0.045 (1) Å. The attached phenyl ring makes a dihedral angle of 86.73 (6)° with the fused ring system. The packing of the molecules in the crystal structure is mainly governed by C—H⋯π hydrogen-bonding interactions.

Related literature

For related preparation and biological activity, see: Bodke & Sangapure (2003 ). For related literature, see: Ding et al., 2004 . For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2005 , 2006 , 2007 ).

Experimental

Crystal data

C₁₉H₁₂N₂O₃
M_r = 316.31
Monoclinic, P 2₁ /n
a = 12.6748 (13) Å
b = 7.1531 (7) Å
c = 17.5793 (17) Å
β = 104.645 (2)°
V = 1542.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 292 (2) K
0.30 × 0.20 × 0.06 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.972, T_max = 0.994
9340 measured reflections
3496 independent reflections
2681 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.119
S = 1.02
3496 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1ⁱ	0.93	2.78	3.529 (1)	138
C4—H4⋯Cg2ⁱⁱ	0.93	2.81	3.641 (1)	150
C11—H11A⋯Cg2ⁱⁱⁱ	0.97	2.76	3.402 (1)	124
C31—H13⋯Cg1^iv	0.93	2.77	3.521 (1)	139
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C14–C19 phenyl ring and Cg2 is the centroid of the C1–C6 ring.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2001 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053680706326X/bt2655sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706326X/bt2655Isup2.hkl

checkCIF report

Comment top

Benzofuropyrimidine derivatives are of interest as possible antiviral agents, and because of their other biological properties, including antibacterial, antifungal, antiallergic and antiinflammatory activities (Bodke & Sangapure, 2003). We have recently focused on the synthesis of the fused heterocyclic systems containing pyrimidinone via aza-Wittig reactions at room temperature (Ding et al., 2004). We present here the structure of one such benzofuropyrimidinone derivative. Fig. 1 shows the molecular structure of (I) with the atomic numbering scheme. Bond lengths and angles are unexceptional (Hu et al., 2005, 2006, 2007). The benzofuropyrimidine ring system is almost planar, with a maximum deviation of 0.045 (6) Å for atom C7; the C14—C19 phenyl ring is twisted with respect to it, with a dihedral angle of 86.73 (6)°. In the crystal, intermolecular C—H···π hydrogen bonds (Table 1) stabilize the crystal structure (Fig. 2).

Related literature top

For related preparation and biological activity, see: Bodke & Sangapure (2003). For related literature, see: Ding et al., 2004. For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2005, 2006, 2007). Cg1 is the centroid of the C14–C19 phenyl ring and Cg2 is the centroid of the C1–C6 ring.

Experimental top

To a solution of ethyl 3-((phenylimino)methyleneamino)benzofuran-2-carboxylate (3 mmol) in dichloromethane (5 ml) was added sodium prop-2-yn-1-oxide (3 mmol) in prop-2-yn-1-ol (5 ml). After stirring the reaction mixture for 2 h, the solvent was removed under reduced pressure and the residue was recrystallized from ethanol to give the title compound, in a yield of 89%. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:1 v/v) at room temperature.

Structure description top

For related preparation and biological activity, see: Bodke & Sangapure (2003). For related literature, see: Ding et al., 2004. For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2005, 2006, 2007). Cg1 is the centroid of the C14–C19 phenyl ring and Cg2 is the centroid of the C1–C6 ring.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The packing in the crystal structure, showing C—H···π hydrogen bonding interactions as dashed lines.

3-Phenyl-2-(prop-2-ynyloxy)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one top

Crystal data top

C₁₉H₁₂N₂O₃	F(000) = 656
M_r = 316.31	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3101 reflections
a = 12.6748 (13) Å	θ = 2.4–27.4°
b = 7.1531 (7) Å	µ = 0.09 mm⁻¹
c = 17.5793 (17) Å	T = 292 K
β = 104.645 (2)°	Block, colorless
V = 1542.0 (3) Å³	0.30 × 0.20 × 0.06 mm
Z = 4

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3496 independent reflections
Radiation source: fine-focus sealed tube	2681 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→16
T_min = 0.972, T_max = 0.994	k = −9→8
9340 measured reflections	l = −22→22

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0641P)²] where P = (F_o² + 2F_c²)/3
3496 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₉H₁₂N₂O₃	V = 1542.0 (3) Å³
M_r = 316.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.6748 (13) Å	µ = 0.09 mm⁻¹
b = 7.1531 (7) Å	T = 292 K
c = 17.5793 (17) Å	0.30 × 0.20 × 0.06 mm
β = 104.645 (2)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3496 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2681 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.994	R_int = 0.041
9340 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.02	Δρ_max = 0.16 e Å⁻³
3496 reflections	Δρ_min = −0.22 e Å⁻³
217 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	1.05495 (11)	0.81800 (18)	0.22716 (7)	0.0377 (3)
C2	1.11240 (12)	0.85724 (19)	0.30421 (8)	0.0455 (4)
H2	1.1116	0.7745	0.3449	0.055*
C3	1.17039 (12)	1.0220 (2)	0.31838 (9)	0.0510 (4)
H3	1.2099	1.0502	0.3693	0.061*
C4	1.17078 (13)	1.1476 (2)	0.25748 (10)	0.0522 (4)
H4	1.2099	1.2584	0.2691	0.063*
C5	1.11500 (12)	1.1122 (2)	0.18077 (9)	0.0482 (4)
H5	1.1156	1.1953	0.1402	0.058*
C6	1.05806 (11)	0.9455 (2)	0.16777 (7)	0.0403 (3)
C7	0.95602 (11)	0.7144 (2)	0.11079 (7)	0.0409 (3)
C8	0.98690 (11)	0.66798 (18)	0.18824 (7)	0.0380 (3)
C9	0.88390 (12)	0.6046 (2)	0.05294 (8)	0.0454 (4)
C10	0.88737 (11)	0.40745 (19)	0.16784 (7)	0.0397 (3)
C11	0.88258 (13)	0.1884 (2)	0.26800 (8)	0.0467 (4)
H11A	0.9608	0.2064	0.2860	0.056*
H11B	0.8678	0.0561	0.2716	0.056*
C12	0.82912 (12)	0.2919 (2)	0.31909 (8)	0.0456 (4)
C13	0.78913 (15)	0.3726 (2)	0.36209 (10)	0.0625 (5)
H13	0.7572	0.4371	0.3964	0.075*
C14	0.76773 (12)	0.32631 (18)	0.03895 (7)	0.0400 (3)
C15	0.79825 (13)	0.1850 (2)	−0.00388 (8)	0.0468 (4)
H15	0.8715	0.1633	−0.0009	0.056*
C16	0.71813 (15)	0.0755 (2)	−0.05158 (9)	0.0555 (4)
H16	0.7378	−0.0211	−0.0806	0.067*
C17	0.60970 (15)	0.1081 (2)	−0.05642 (9)	0.0583 (4)
H17	0.5563	0.0355	−0.0893	0.070*
C18	0.58085 (13)	0.2486 (3)	−0.01233 (10)	0.0612 (5)
H18	0.5077	0.2693	−0.0146	0.073*
C19	0.65962 (13)	0.3592 (2)	0.03527 (9)	0.0555 (4)
H19	0.6399	0.4551	0.0646	0.067*
N1	0.95387 (9)	0.50832 (16)	0.21918 (6)	0.0416 (3)
N2	0.85008 (9)	0.44489 (16)	0.08854 (6)	0.0413 (3)
O1	0.99762 (8)	0.88383 (13)	0.09524 (5)	0.0461 (3)
O2	0.85057 (11)	0.63467 (16)	−0.01731 (6)	0.0670 (4)
O3	0.84625 (9)	0.24665 (14)	0.18664 (5)	0.0495 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0361 (7)	0.0393 (7)	0.0367 (7)	0.0037 (6)	0.0071 (6)	0.0010 (5)
C2	0.0483 (8)	0.0460 (9)	0.0378 (7)	0.0050 (6)	0.0027 (6)	0.0011 (6)
C3	0.0485 (9)	0.0527 (9)	0.0455 (8)	0.0006 (7)	0.0003 (7)	−0.0085 (7)
C4	0.0470 (9)	0.0486 (9)	0.0597 (9)	−0.0061 (7)	0.0112 (7)	−0.0075 (7)
C5	0.0487 (9)	0.0489 (9)	0.0490 (8)	−0.0044 (7)	0.0161 (7)	0.0043 (7)
C6	0.0378 (7)	0.0472 (8)	0.0356 (7)	0.0017 (6)	0.0087 (6)	−0.0002 (6)
C7	0.0459 (8)	0.0434 (8)	0.0327 (7)	−0.0017 (6)	0.0086 (6)	0.0042 (6)
C8	0.0382 (7)	0.0410 (8)	0.0331 (7)	0.0049 (6)	0.0055 (6)	0.0014 (5)
C9	0.0517 (9)	0.0499 (9)	0.0326 (7)	−0.0026 (7)	0.0070 (6)	0.0031 (6)
C10	0.0450 (8)	0.0407 (7)	0.0319 (7)	0.0003 (6)	0.0070 (6)	0.0028 (6)
C11	0.0588 (9)	0.0415 (8)	0.0377 (7)	0.0021 (7)	0.0082 (7)	0.0091 (6)
C12	0.0475 (9)	0.0474 (9)	0.0390 (8)	−0.0010 (7)	0.0055 (6)	0.0067 (6)
C13	0.0673 (11)	0.0661 (11)	0.0560 (10)	0.0056 (9)	0.0194 (9)	−0.0024 (8)
C14	0.0468 (8)	0.0405 (8)	0.0295 (6)	0.0001 (6)	0.0040 (6)	0.0004 (5)
C15	0.0527 (9)	0.0495 (9)	0.0385 (7)	0.0036 (7)	0.0124 (7)	0.0015 (6)
C16	0.0757 (12)	0.0456 (9)	0.0444 (8)	0.0005 (8)	0.0135 (8)	−0.0092 (7)
C17	0.0628 (11)	0.0528 (10)	0.0509 (9)	−0.0088 (8)	−0.0011 (8)	−0.0049 (7)
C18	0.0433 (9)	0.0667 (11)	0.0666 (11)	0.0016 (8)	0.0009 (8)	−0.0073 (9)
C19	0.0515 (10)	0.0567 (10)	0.0551 (9)	0.0076 (7)	0.0075 (7)	−0.0141 (7)
N1	0.0489 (7)	0.0410 (7)	0.0319 (6)	−0.0009 (5)	0.0048 (5)	0.0028 (5)
N2	0.0475 (7)	0.0443 (7)	0.0290 (5)	−0.0030 (5)	0.0041 (5)	−0.0005 (5)
O1	0.0533 (6)	0.0497 (6)	0.0342 (5)	−0.0078 (5)	0.0087 (4)	0.0047 (4)
O2	0.0928 (9)	0.0695 (8)	0.0301 (5)	−0.0207 (7)	−0.0005 (5)	0.0078 (5)
O3	0.0649 (7)	0.0460 (6)	0.0339 (5)	−0.0101 (5)	0.0058 (5)	0.0040 (4)

Geometric parameters (Å, º) top

C1—C6	1.3941 (19)	C10—N2	1.3804 (16)
C1—C2	1.3946 (18)	C11—O3	1.4486 (15)
C1—C8	1.4371 (18)	C11—C12	1.457 (2)
C2—C3	1.378 (2)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.398 (2)	C12—C13	1.164 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.379 (2)	C14—C15	1.3731 (19)
C4—H4	0.9300	C14—C19	1.376 (2)
C5—C6	1.383 (2)	C14—N2	1.4522 (17)
C5—H5	0.9300	C15—C16	1.385 (2)
C6—O1	1.3832 (15)	C15—H15	0.9300
C7—C8	1.3593 (18)	C16—C17	1.375 (2)
C7—O1	1.3766 (16)	C16—H16	0.9300
C7—C9	1.4200 (19)	C17—C18	1.374 (2)
C8—N1	1.3749 (16)	C17—H17	0.9300
C9—O2	1.2190 (16)	C18—C19	1.378 (2)
C9—N2	1.4199 (18)	C18—H18	0.9300
C10—N1	1.2888 (17)	C19—H19	0.9300
C10—O3	1.3382 (16)

C6—C1—C2	119.28 (13)	O3—C11—H11A	109.1
C6—C1—C8	105.01 (11)	C12—C11—H11A	109.1
C2—C1—C8	135.71 (12)	O3—C11—H11B	109.1
C3—C2—C1	118.12 (13)	C12—C11—H11B	109.1
C3—C2—H2	120.9	H11A—C11—H11B	107.9
C1—C2—H2	120.9	C13—C12—C11	177.69 (16)
C2—C3—C4	121.05 (14)	C12—C13—H13	180.0
C2—C3—H3	119.5	C15—C14—C19	121.04 (13)
C4—C3—H3	119.5	C15—C14—N2	119.98 (13)
C5—C4—C3	122.07 (14)	C19—C14—N2	118.98 (12)
C5—C4—H4	119.0	C14—C15—C16	118.90 (15)
C3—C4—H4	119.0	C14—C15—H15	120.6
C4—C5—C6	115.92 (13)	C16—C15—H15	120.6
C4—C5—H5	122.0	C17—C16—C15	120.66 (14)
C6—C5—H5	122.0	C17—C16—H16	119.7
C5—C6—O1	124.85 (12)	C15—C16—H16	119.7
C5—C6—C1	123.55 (12)	C18—C17—C16	119.57 (15)
O1—C6—C1	111.59 (12)	C18—C17—H17	120.2
C8—C7—O1	112.72 (12)	C16—C17—H17	120.2
C8—C7—C9	123.55 (13)	C17—C18—C19	120.47 (16)
O1—C7—C9	123.65 (12)	C17—C18—H18	119.8
C7—C8—N1	124.03 (12)	C19—C18—H18	119.8
C7—C8—C1	106.30 (12)	C14—C19—C18	119.36 (14)
N1—C8—C1	129.65 (12)	C14—C19—H19	120.3
O2—C9—N2	121.50 (13)	C18—C19—H19	120.3
O2—C9—C7	128.57 (14)	C10—N1—C8	113.50 (11)
N2—C9—C7	109.92 (11)	C10—N2—C9	122.46 (11)
N1—C10—O3	122.34 (12)	C10—N2—C14	120.23 (11)
N1—C10—N2	126.51 (13)	C9—N2—C14	117.18 (10)
O3—C10—N2	111.15 (11)	C7—O1—C6	104.37 (10)
O3—C11—C12	112.40 (12)	C10—O3—C11	116.41 (11)

C6—C1—C2—C3	0.0 (2)	C16—C17—C18—C19	1.4 (3)
C8—C1—C2—C3	179.90 (15)	C15—C14—C19—C18	−0.1 (2)
C1—C2—C3—C4	0.7 (2)	N2—C14—C19—C18	179.27 (14)
C2—C3—C4—C5	−0.9 (2)	C17—C18—C19—C14	−0.7 (3)
C3—C4—C5—C6	0.4 (2)	O3—C10—N1—C8	179.94 (12)
C4—C5—C6—O1	−179.66 (13)	N2—C10—N1—C8	0.8 (2)
C4—C5—C6—C1	0.3 (2)	C7—C8—N1—C10	−1.97 (19)
C2—C1—C6—C5	−0.5 (2)	C1—C8—N1—C10	176.24 (13)
C8—C1—C6—C5	179.57 (13)	N1—C10—N2—C9	1.1 (2)
C2—C1—C6—O1	179.48 (12)	O3—C10—N2—C9	−178.16 (12)
C8—C1—C6—O1	−0.48 (14)	N1—C10—N2—C14	−174.64 (13)
O1—C7—C8—N1	178.20 (12)	O3—C10—N2—C14	6.10 (17)
C9—C7—C8—N1	1.4 (2)	O2—C9—N2—C10	179.54 (13)
O1—C7—C8—C1	−0.37 (16)	C7—C9—N2—C10	−1.62 (19)
C9—C7—C8—C1	−177.17 (13)	O2—C9—N2—C14	−4.6 (2)
C6—C1—C8—C7	0.50 (14)	C7—C9—N2—C14	174.25 (12)
C2—C1—C8—C7	−179.45 (15)	C15—C14—N2—C10	−96.71 (16)
C6—C1—C8—N1	−177.95 (13)	C19—C14—N2—C10	83.87 (17)
C2—C1—C8—N1	2.1 (3)	C15—C14—N2—C9	87.32 (15)
C8—C7—C9—O2	179.20 (15)	C19—C14—N2—C9	−92.09 (16)
O1—C7—C9—O2	2.7 (3)	C8—C7—O1—C6	0.08 (15)
C8—C7—C9—N2	0.5 (2)	C9—C7—O1—C6	176.88 (13)
O1—C7—C9—N2	−176.00 (12)	C5—C6—O1—C7	−179.79 (13)
O3—C11—C12—C13	−164 (4)	C1—C6—O1—C7	0.26 (14)
C19—C14—C15—C16	0.3 (2)	N1—C10—O3—C11	−1.5 (2)
N2—C14—C15—C16	−179.10 (12)	N2—C10—O3—C11	177.81 (11)
C14—C15—C16—C17	0.4 (2)	C12—C11—O3—C10	77.20 (16)
C15—C16—C17—C18	−1.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ⁱ	0.93	2.78	3.529 (1)	138
C4—H4···Cg2ⁱⁱ	0.93	2.81	3.641 (1)	150
C11—H11A···Cg2ⁱⁱⁱ	0.97	2.76	3.402 (1)	124
C31—H13···Cg1^iv	0.93	2.77	3.521 (1)	139

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+5/2, y+1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₂N₂O₃
M_r	316.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	292
a, b, c (Å)	12.6748 (13), 7.1531 (7), 17.5793 (17)
β (°)	104.645 (2)
V (Å³)	1542.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.06

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.972, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	9340, 3496, 2681
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.119, 1.02
No. of reflections	3496
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.22

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ⁱ	0.93	2.78	3.529 (1)	138
C4—H4···Cg2ⁱⁱ	0.93	2.81	3.641 (1)	150
C11—H11A···Cg2ⁱⁱⁱ	0.97	2.76	3.402 (1)	124
C31—H13···Cg1^iv	0.93	2.77	3.521 (1)	139

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+5/2, y+1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

We gratefully acknowledge financial support of this work by the Key Science Research Project of Hubei Provincial Department of Education (No. D200724001) and the Science Research Project of Yunyang Medical College (No. 2006QDJ16).

References

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