3-(4-Bromo­phen­yl)-4-(4-hy­droxy­anilino)furan-2(5H)-one

Peng, W.; Wang, L.; Wu, F.; Xu, Q.

doi:10.1107/S1600536811031849

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2329

doi:10.1107/S1600536811031849

Open

access

3-(4-Bromophenyl)-4-(4-hydroxyanilino)furan-2(5H)-one

Wanxi Peng,^a ^* Lansheng Wang,^a Fengjuan Wu ^a and Qiu Xu ^a

^aSchool of Materials Science and Engineering, Central South University of Forestry and Technology, Changsha 410004, People's Republic of China
^*Correspondence e-mail: pengwanxi@163.com

(Received 28 July 2011; accepted 6 August 2011; online 11 August 2011)

In the title compound, C₁₆H₁₂BrNO₃, the butyrolactone core adopts the furan-2(5H)-one structure and forms dihedral angles of 44.80 (17) and 65.73 (18)° with the bromobenzene and phenol rings, respectively. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the molecules, generating R₄³(26) loops The edge-fused rings extend to form a chain running along the b-axis direction and C—H⋯π contacts help to consolidate the packing.

Related literature

For biological background to furan-2(5H)-one derivatives, see: Bailly et al. (2008 ); Weber et al. (2005 ); Xiao et al. (2011a ,b ). For related structures, see: Xiao et al. (2010 , 2011c ).

Experimental

Crystal data

C₁₆H₁₂BrNO₃
M_r = 346.18
Monoclinic, P 2₁ /c
a = 11.2418 (10) Å
b = 8.0545 (7) Å
c = 16.1138 (13) Å
β = 100.244 (4)°
V = 1435.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.87 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.597, T_max = 0.762
7599 measured reflections
2725 independent reflections
1650 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.108
S = 1.01
2725 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.76 (4)	2.56 (4)	3.207 (4)	144 (4)
O3—H3A⋯O1ⁱⁱ	0.82	1.90	2.700 (4)	165
C12—H12⋯Cg1ⁱ	0.93	2.86	3.723 (4)	155
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031849/hb6341sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031849/hb6341Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031849/hb6341Isup3.cml

checkCIF report

Comment top

Many compounds with γ-butyrolactone-core (furanone) show diverse biological activities such as antitumor and anti-inflammatory activity (Bailly et al., 2008; Weber et al., 2005). Recently, Xiao and his co-workers reported that 4-alkylamino or 4-arylamino derivatives of 3-arylfuran-2(5H)-one are potent inhibitors against tyrosyl-tRNA synthetase (TyrRS) (Xiao et al., 2011a and 2011b), one of the aminoacyl-tRNA synthetases (aaRSs). Herein, we report the crystal structure of the title compound (I) (Fig. 1), an 3-aryl-4-arylaminofuran-2(5H)-one.

The bond C7—C10 (1.364 (4) Å) was assigned as a double bond, and the title compound was therefore identified as a furan-2(5H)-one (Xiao et al., 2010; Xiao et al., 2011c). C10—N1 (1.332 (4) Å) bond has shorter bond distance than the standard C—N single bond (1.48 Å), but longer than 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. However, the bond distance of C11—N1 is 1.437 (4) Å, much longer than that of C10—N1. This may be caused by the large dihedral angle [65.76 (28) °] between the amino group (C10, C11, N1 and H1) and the 4-hydroxybenzene ring, which significantly disrupted the conjugation between N1 and its attached benzene ring.

In the crystal, four molecules of I are connected by intermolecular N1—H1···O1 and O3—H3A···O1 interactions to generate a ring motif described by a graph-set motif of R₄³(26) (Fig. 2). The edge-fused rings extend to form a sheet running along the b axis. The resulted sheet is further stablized by C—H···π contacts (Fig. 3).

Related literature top

For biological background to furan-2(5H)-one derivatives, see: Bailly et al. (2008); Weber et al. (2005); Xiao et al. (2011a,b). For related structures, see: Xiao et al. (2010, 2011c).

Experimental top

3-(4-bromophenyl)-4-hydroxyfuran-2(5H)-one (255 mg, 1 mmol) was prepared according to the procedure described by Xiao (Xiao et al., 2011a), which was added into a mixture of 4-hydroxyaniline (130 mg, 1.2 mmol) and p-toluene sulphonic acid (6.8 mg, 0.04 mmol). The resulted mixture was heated to 370 K for 10 min. Nine ml of toluene was then added and refluxed for 6 h. After toluene was removed under reduced pressure, the residue was purified by column chromatography on silica gel, eluting with EtOAc/petroleum ether (v/v = 2/1), which furnished colorless blocks of I by slow evaporation at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Motifs of R₄³(26) are formed through intermolecular N—H···O and O—H···O hydrogen bonds. For the sake of clarity, the H atoms not involved in the hydrogen bonds have been omitted.
	Fig. 3. Packing diagram of compound (I) viewing along c axis, Solid dashed lines indicate C—H···π contacts. For the sake of clarity, the H atoms not involved in the hydrogen bonds have been omitted.

3-(4-Bromophenyl)-4-(4-hydroxyanilino)furan-2(5H)-one top

Crystal data top

C₁₆H₁₂BrNO₃	F(000) = 696
M_r = 346.18	D_x = 1.601 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1582 reflections
a = 11.2418 (10) Å	θ = 2.1–25.1°
b = 8.0545 (7) Å	µ = 2.87 mm⁻¹
c = 16.1138 (13) Å	T = 296 K
β = 100.244 (4)°	Block, colorless
V = 1435.8 (2) Å³	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker APEX CCD diffractometer	2725 independent reflections
Radiation source: fine-focus sealed tube	1650 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 25.8°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→10
T_min = 0.597, T_max = 0.762	k = −9→9
7599 measured reflections	l = −18→19

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0519P)² + 0.1637P] where P = (F_o² + 2F_c²)/3
2725 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₆H₁₂BrNO₃	V = 1435.8 (2) Å³
M_r = 346.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2418 (10) Å	µ = 2.87 mm⁻¹
b = 8.0545 (7) Å	T = 296 K
c = 16.1138 (13) Å	0.20 × 0.20 × 0.10 mm
β = 100.244 (4)°

Data collection top

Bruker APEX CCD diffractometer	2725 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1650 reflections with I > 2σ(I)
T_min = 0.597, T_max = 0.762	R_int = 0.035
7599 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.27 e Å⁻³
2725 reflections	Δρ_min = −0.59 e Å⁻³
195 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
Br1	−0.33348 (4)	0.01420 (6)	−0.05871 (2)	0.0870 (2)
C1	−0.0793 (3)	0.0631 (4)	0.2028 (2)	0.0449 (8)
C2	−0.1939 (3)	−0.0066 (4)	0.1953 (2)	0.0506 (8)
H2	−0.2201	−0.0450	0.2435	0.061*
C3	−0.2695 (3)	−0.0201 (4)	0.1185 (2)	0.0544 (9)
H3	−0.3466	−0.0647	0.1148	0.065*
C4	−0.2294 (3)	0.0333 (4)	0.0473 (2)	0.0512 (9)
C5	−0.1167 (3)	0.1009 (4)	0.0516 (2)	0.0549 (9)
H5	−0.0908	0.1361	0.0028	0.066*
C6	−0.0417 (3)	0.1162 (4)	0.1293 (2)	0.0522 (8)
H6	0.0347	0.1625	0.1324	0.063*
C7	−0.0029 (3)	0.0832 (4)	0.28604 (19)	0.0452 (8)
C8	−0.0498 (3)	0.1479 (4)	0.3561 (2)	0.0548 (9)
C9	0.1485 (3)	0.0909 (4)	0.4049 (2)	0.0549 (9)
H9A	0.1731	−0.0102	0.4360	0.066*
H9B	0.2132	0.1718	0.4172	0.066*
C10	0.1178 (3)	0.0571 (4)	0.31223 (19)	0.0447 (8)
C11	0.3288 (3)	0.0027 (4)	0.3037 (2)	0.0485 (8)
C12	0.3717 (3)	−0.1054 (4)	0.3681 (2)	0.0632 (10)
H12	0.3191	−0.1784	0.3879	0.076*
C13	0.4933 (3)	−0.1054 (5)	0.4032 (2)	0.0690 (10)
H13	0.5224	−0.1783	0.4469	0.083*
C14	0.5709 (3)	0.0011 (5)	0.3740 (2)	0.0603 (10)
C15	0.5287 (3)	0.1075 (5)	0.3088 (2)	0.0575 (9)
H15	0.5817	0.1787	0.2881	0.069*
C16	0.4072 (3)	0.1084 (4)	0.27397 (19)	0.0517 (8)
H16	0.3784	0.1810	0.2301	0.062*
N1	0.2020 (3)	0.0087 (4)	0.2687 (2)	0.0594 (8)
O1	−0.1497 (2)	0.2035 (4)	0.36051 (14)	0.0755 (8)
O2	0.03891 (19)	0.1547 (3)	0.42643 (13)	0.0621 (6)
O3	0.6898 (2)	−0.0049 (4)	0.4118 (2)	0.0954 (10)
H3A	0.7279	0.0661	0.3911	0.143*
H1	0.187 (3)	−0.027 (4)	0.224 (2)	0.062 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0902 (4)	0.1047 (4)	0.0567 (3)	−0.0269 (2)	−0.0122 (2)	0.0012 (2)
C1	0.0419 (18)	0.0458 (18)	0.0469 (18)	−0.0003 (14)	0.0078 (14)	−0.0035 (15)
C2	0.046 (2)	0.057 (2)	0.0502 (19)	−0.0069 (16)	0.0130 (15)	0.0000 (16)
C3	0.047 (2)	0.057 (2)	0.058 (2)	−0.0081 (16)	0.0074 (16)	−0.0011 (17)
C4	0.057 (2)	0.043 (2)	0.051 (2)	0.0020 (16)	0.0011 (16)	−0.0051 (15)
C5	0.061 (2)	0.060 (2)	0.0455 (19)	−0.0004 (18)	0.0133 (16)	0.0042 (16)
C6	0.0436 (18)	0.060 (2)	0.055 (2)	−0.0065 (16)	0.0131 (15)	0.0012 (17)
C7	0.0409 (18)	0.0498 (19)	0.0460 (18)	−0.0022 (15)	0.0109 (14)	−0.0043 (15)
C8	0.045 (2)	0.070 (2)	0.049 (2)	−0.0012 (18)	0.0066 (16)	−0.0012 (17)
C9	0.046 (2)	0.060 (2)	0.057 (2)	0.0035 (17)	0.0053 (16)	−0.0054 (18)
C10	0.0414 (19)	0.0432 (18)	0.0503 (19)	−0.0064 (14)	0.0100 (15)	−0.0048 (14)
C11	0.0401 (19)	0.054 (2)	0.0519 (19)	0.0012 (16)	0.0089 (15)	−0.0112 (17)
C12	0.055 (2)	0.050 (2)	0.088 (3)	−0.0011 (17)	0.021 (2)	0.0051 (19)
C13	0.060 (2)	0.070 (3)	0.077 (3)	0.019 (2)	0.013 (2)	0.016 (2)
C14	0.039 (2)	0.080 (3)	0.062 (2)	0.0043 (18)	0.0085 (17)	0.003 (2)
C15	0.0407 (19)	0.078 (3)	0.055 (2)	−0.0114 (17)	0.0119 (16)	0.0001 (19)
C16	0.050 (2)	0.066 (2)	0.0410 (18)	0.0016 (18)	0.0111 (15)	−0.0016 (16)
N1	0.0412 (17)	0.079 (2)	0.058 (2)	−0.0017 (14)	0.0086 (15)	−0.0229 (18)
O1	0.0518 (15)	0.115 (2)	0.0616 (16)	0.0171 (14)	0.0139 (12)	−0.0101 (14)
O2	0.0556 (14)	0.0847 (18)	0.0457 (13)	0.0084 (12)	0.0087 (11)	−0.0092 (12)
O3	0.0431 (16)	0.147 (3)	0.091 (2)	0.0103 (15)	−0.0021 (14)	0.0237 (18)

Geometric parameters (Å, º) top

Br1—C4	1.897 (3)	C9—H9A	0.9700
C1—C2	1.391 (4)	C9—H9B	0.9700
C1—C6	1.394 (4)	C10—N1	1.332 (4)
C1—C7	1.467 (4)	C11—C16	1.371 (4)
C2—C3	1.376 (5)	C11—C12	1.375 (5)
C2—H2	0.9300	C11—N1	1.437 (4)
C3—C4	1.373 (5)	C12—C13	1.384 (5)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.369 (5)	C13—C14	1.366 (5)
C5—C6	1.384 (4)	C13—H13	0.9300
C5—H5	0.9300	C14—O3	1.368 (4)
C6—H6	0.9300	C14—C15	1.373 (5)
C7—C10	1.364 (4)	C15—C16	1.381 (4)
C7—C8	1.428 (4)	C15—H15	0.9300
C8—O1	1.222 (4)	C16—H16	0.9300
C8—O2	1.371 (3)	N1—H1	0.76 (4)
C9—O2	1.433 (4)	O3—H3A	0.8200
C9—C10	1.497 (4)

C2—C1—C6	117.8 (3)	C10—C9—H9B	110.8
C2—C1—C7	120.4 (3)	H9A—C9—H9B	108.9
C6—C1—C7	121.8 (3)	N1—C10—C7	130.0 (3)
C3—C2—C1	121.6 (3)	N1—C10—C9	121.3 (3)
C3—C2—H2	119.2	C7—C10—C9	108.7 (3)
C1—C2—H2	119.2	C16—C11—C12	119.7 (3)
C4—C3—C2	119.0 (3)	C16—C11—N1	119.8 (3)
C4—C3—H3	120.5	C12—C11—N1	120.5 (3)
C2—C3—H3	120.5	C11—C12—C13	119.8 (3)
C5—C4—C3	121.4 (3)	C11—C12—H12	120.1
C5—C4—Br1	119.6 (3)	C13—C12—H12	120.1
C3—C4—Br1	119.0 (3)	C14—C13—C12	120.2 (3)
C4—C5—C6	119.3 (3)	C14—C13—H13	119.9
C4—C5—H5	120.3	C12—C13—H13	119.9
C6—C5—H5	120.3	C13—C14—O3	117.2 (3)
C5—C6—C1	120.9 (3)	C13—C14—C15	120.1 (3)
C5—C6—H6	119.6	O3—C14—C15	122.7 (3)
C1—C6—H6	119.6	C14—C15—C16	119.7 (3)
C10—C7—C8	107.4 (3)	C14—C15—H15	120.1
C10—C7—C1	130.9 (3)	C16—C15—H15	120.1
C8—C7—C1	121.6 (3)	C11—C16—C15	120.4 (3)
O1—C8—O2	118.6 (3)	C11—C16—H16	119.8
O1—C8—C7	130.7 (3)	C15—C16—H16	119.8
O2—C8—C7	110.6 (3)	C10—N1—C11	123.4 (3)
O2—C9—C10	104.5 (2)	C10—N1—H1	123 (3)
O2—C9—H9A	110.8	C11—N1—H1	113 (3)
C10—C9—H9A	110.8	C8—O2—C9	108.4 (2)
O2—C9—H9B	110.8	C14—O3—H3A	109.5

C6—C1—C2—C3	−1.3 (5)	C1—C7—C10—C9	−177.8 (3)
C7—C1—C2—C3	177.0 (3)	O2—C9—C10—N1	174.5 (3)
C1—C2—C3—C4	1.5 (5)	O2—C9—C10—C7	−6.0 (4)
C2—C3—C4—C5	−0.7 (5)	C16—C11—C12—C13	0.9 (5)
C2—C3—C4—Br1	179.8 (2)	N1—C11—C12—C13	−177.6 (3)
C3—C4—C5—C6	−0.2 (5)	C11—C12—C13—C14	−0.3 (6)
Br1—C4—C5—C6	179.3 (2)	C12—C13—C14—O3	179.7 (4)
C4—C5—C6—C1	0.3 (5)	C12—C13—C14—C15	−0.8 (6)
C2—C1—C6—C5	0.4 (5)	C13—C14—C15—C16	1.2 (5)
C7—C1—C6—C5	−177.9 (3)	O3—C14—C15—C16	−179.3 (3)
C2—C1—C7—C10	138.5 (4)	C12—C11—C16—C15	−0.5 (5)
C6—C1—C7—C10	−43.2 (5)	N1—C11—C16—C15	178.0 (3)
C2—C1—C7—C8	−45.2 (4)	C14—C15—C16—C11	−0.5 (5)
C6—C1—C7—C8	133.1 (3)	C7—C10—N1—C11	173.4 (3)
C10—C7—C8—O1	172.4 (4)	C9—C10—N1—C11	−7.2 (5)
C1—C7—C8—O1	−4.6 (6)	C16—C11—N1—C10	−113.5 (4)
C10—C7—C8—O2	−2.9 (4)	C12—C11—N1—C10	64.9 (5)
C1—C7—C8—O2	−180.0 (3)	O1—C8—O2—C9	−177.0 (3)
C8—C7—C10—N1	−175.1 (3)	C7—C8—O2—C9	−1.0 (4)
C1—C7—C10—N1	1.6 (6)	C10—C9—O2—C8	4.2 (3)
C8—C7—C10—C9	5.5 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.76 (4)	2.56 (4)	3.207 (4)	144 (4)
O3—H3A···O1ⁱⁱ	0.82	1.90	2.700 (4)	165
C12—H12···Cg1ⁱ	0.93	2.86	3.723 (4)	155

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂BrNO₃
M_r	346.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.2418 (10), 8.0545 (7), 16.1138 (13)
β (°)	100.244 (4)
V (Å³)	1435.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.87
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.597, 0.762
No. of measured, independent and observed [I > 2σ(I)] reflections	7599, 2725, 1650
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.612

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.108, 1.01
No. of reflections	2725
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.59

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.76 (4)	2.56 (4)	3.207 (4)	144 (4)
O3—H3A···O1ⁱⁱ	0.82	1.90	2.700 (4)	165.3
C12—H12···Cg1ⁱ	0.93	2.86	3.723 (4)	155

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

Acknowledgements

This work was financed by a project supported by the National Natural Science Foundation of China (No. 31070497), the Program for New Century Excellent Talents in Universities, a project supported by the Scientific Research Fund of Hunan Provincial Education Department (No. 10 A131) and a key (key grant) project of the Chinese Ministry of Education (No. 211128).

References

Bailly, F., Queffèlec, C., Mbemba, G., Mouscadet, J. F., Pommery, N., Pommery, J., Hènichart, J. P. & Cotelle, P. (2008). Eur. J. Med. Chem. 43, 1222–1229. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2000). 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
Weber, V., Rubat, C., Duroux, E., Lartigue, C., Madesclaire, M. & Coudert, P. (2005). Bioorg. Med. Chem. 13, 4552–4564. Web of Science CrossRef PubMed CAS Google Scholar
Xiao, Z.-P., He, X.-B., Peng, Z.-Y., Xiong, T.-J., Peng, J., Chen, L.-H. & Zhu, H.-L. (2011a). Bioorg. Med. Chem. 19, 1571–1579. Web of Science CSD CrossRef CAS PubMed Google Scholar
Xiao, Z.-P., Ouyang, H., Wang, X.-D., Lv, P.-C., Huang, Z.-J., Yu, S.-R., Yi, T.-F., Yang, Y.-L. & Zhu, H.-L. (2011b). Bioorg. Med. Chem. 19, 3884–3891. Web of Science CSD CrossRef CAS PubMed Google Scholar
Xiao, Z.-P., Peng, Z.-Y., Liu, Z.-X., Chen, L.-H. & Zhu, H.-L. (2011c). 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

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 67| Part 9| September 2011| Page o2329

doi:10.1107/S1600536811031849

Open

access