2-Benzoyl­amino-N-[5-(4-bromo­phen­yl)-1,3,4-thia­diazol-2-yl]ethanamide

Huang, H.-M.; Luo, S.-Y.; Li, S.-H.; Liu, C.-M.; Tu, G.-G.

doi:10.1107/S160053680900124X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o325

doi:10.1107/S160053680900124X

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2-Benzoylamino-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]ethanamide

Hui-Ming Huang,^a,^b Shi-Yuan Luo,^b Shao-Hua Li,^b Cheng-Mei Liu ^a ‡ and Guo-Gang Tu ^b ^*

^aState Key Laboratory of Food Science and Technology, Nanchang University, 330047 Nanchang, JiangXi, People's Republic of China, and ^bDepartment of Pharmacy, NanChang University Medical College, 330006 Nanchang, JiangXi, People's Republic of China
^*Correspondence e-mail: tugg199@yahoo.com

(Received 29 December 2008; accepted 10 January 2009; online 17 January 2009)

In the structure of the title compound, C₁₇H₁₃BrN₄O₂S, the dihedral angle between the two benzene rings is 38.5 (1)°; the angle between the 4-bromobenzene and thiadiazole rings is 1.3 (1)°. The conformations of the N—H and C=O bonds are anti with respect to each other. The structure displays intermolecular N—H⋯O and C—H⋯O hydrogen bonding, with both interactions leading to inversion dimers.

Related literature

For 1,3,4-thiadiazole scaffold compounds and their biological activity, see: Tu et al. (2008 ). For the synthesis, see: Foroumadi et al. (1999 ); Levy & Palmer (1942 ); Song et al. (1992 ). For related structures, see: Gowda et al. (2008 ); Li, Huang et al. (2008 ); Li, Li et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₃BrN₄O₂S
M_r = 417.28
Triclinic, $[P \overline 1]$
a = 4.020 (4) Å
b = 13.706 (9) Å
c = 16.210 (5) Å
α = 113.334 (17)°
β = 94.018 (19)°
γ = 92.78 (2)°
V = 815.2 (10) Å³
Z = 2
Mo Kα radiation
μ = 2.67 mm⁻¹
T = 298 (2) K
0.54 × 0.17 × 0.04 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.591, T_max = 0.914
4633 measured reflections
2592 independent reflections
1097 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.109
wR(F²) = 0.281
S = 0.82
2592 reflections
227 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 1.67 e Å⁻³
Δρ_min = −1.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2ⁱ	0.93	2.49	3.400 (5)	168
N2—H2A⋯O1ⁱⁱ	0.86	1.99	2.835 (5)	167
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z.

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: APEX2 (Bruker, 2004); software used to prepare material for publication: APEX2 (Bruker, 2004) and publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900124X/wn2304sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900124X/wn2304Isup2.hkl

checkCIF report

Comment top

In our previous work, 1,3,4-thiadiazole scaffold compounds and their biological activity have been studied (Tu et al., 2008). In view of the importance of these organic materials, the title compound (Fig. 1) was synthesized (Foroumadi et al., 1999; Levy & Palmer 1942; Song et al., 1992) and its crystal structure is reported here.

In the structure of the title compound, C₁₇H₁₃BrN₄O₂S, the dihedral angle between the p-bromobenzene and thiadiazole rings is 1.3 (1)°; the angle between the two benzene rings is 38.5 (1)°. The conformations of the N—H and C═O bonds are anti with respect to each other. Bond lengths and angles are in normal ranges and comparable to those in related structures (Gowda et al., 2008; Li, Huang et al., 2008; Li, Li et al., 2008). In the crystal structure, molecules are linked through intermolecular C—H···O and N—H···O hydrogen bonds, forming a three-dimensional network (Table 1, Figure 2).

Related literature top

For 1,3,4-thiadiazole scaffold compounds and their biological activity, see: Tu et al. (2008). For the synthesis, see: Foroumadi et al. (1999); Levy & Palmer (1942); Song et al. (1992). For related structures, see: Gowda et al. (2008); Li, Huang et al. (2008); Li, Li et al. (2008).

Experimental top

N,N-Dicyclohexylcarbodiimide (5.7 mmol) was added to a cooled solution of N-benzoylglycine (5.6 mmol) and N-hydroxysuccinimide (5.6 mmol) in freshly distilled dioxane (30 ml). The reaction mixture was stirred overnight at room temperature. The insoluble material was filtered off and washed with cold dioxane. 2-Amino-5-(4-bromophenyl)-1,3,4-thiadiazole (5.5 mmol) was added to the filtrate and the reaction mixture was stirred for 48 h at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and the insoluble material was filtered off. The filtrate was washed successively with saturated Na₂CO₃ solution (20 ml, x 3), water (20 ml, x 1), 0.1 M HCl (20 ml, x 3) and water (20 ml, x 1). The organic layer evaporated in vacuo, and the residue was recrystallized from methanol. Colorless block-shaped single crystals of the title compound suitable for X-ray diffraction analysis precipitated after several days.Yield: 37.0%; mp: 271–273°C.

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: APEX2 (Bruker, 2004); software used to prepare material for publication: APEX2 (Bruker, 2004) and publCIF (Westrip, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis with hydrogen bonds drawn as dashed lines.

2-Benzoylamino-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]ethanamide top

Crystal data top

C₁₇H₁₃BrN₄O₂S	Z = 2
M_r = 417.28	F(000) = 420.0
Triclinic, P1	D_x = 1.700 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.020 (4) Å	Cell parameters from 1179 reflections
b = 13.706 (9) Å	θ = 2.6–23.7°
c = 16.210 (5) Å	µ = 2.67 mm⁻¹
α = 113.334 (17)°	T = 298 K
β = 94.018 (19)°	Block, colourless
γ = 92.78 (2)°	0.54 × 0.17 × 0.04 mm
V = 815.2 (10) Å³

Data collection top

Bruker X8 APEXII diffractometer	2592 independent reflections
Radiation source: fine-focus sealed tube	1097 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −4→4
T_min = 0.591, T_max = 0.914	k = −16→16
4633 measured reflections	l = −19→19

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)] = 0.109	H-atom parameters constrained
wR(F²) = 0.281	w = 1/[σ²(F_o²) + (0.1951P)²] where P = (F_o² + 2F_c²)/3
S = 0.82	(Δ/σ)_max = 0.019
2592 reflections	Δρ_max = 1.67 e Å⁻³
227 parameters	Δρ_min = −1.40 e Å⁻³
6 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: 0.022 (2)

Crystal data top

C₁₇H₁₃BrN₄O₂S	γ = 92.78 (2)°
M_r = 417.28	V = 815.2 (10) Å³
Triclinic, P1	Z = 2
a = 4.020 (4) Å	Mo Kα radiation
b = 13.706 (9) Å	µ = 2.67 mm⁻¹
c = 16.210 (5) Å	T = 298 K
α = 113.334 (17)°	0.54 × 0.17 × 0.04 mm
β = 94.018 (19)°

Data collection top

Bruker X8 APEXII diffractometer	2592 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1097 reflections with I > 2σ(I)
T_min = 0.591, T_max = 0.914	R_int = 0.082
4633 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.109	6 restraints
wR(F²) = 0.281	H-atom parameters constrained
S = 0.82	Δρ_max = 1.67 e Å⁻³
2592 reflections	Δρ_min = −1.40 e Å⁻³
227 parameters

Special details top

Experimental. ¹H-NMR (DMSO-d6): δ 4.24–4.25(d, J=5.08 Hz, 2H), 7.49–7.57 (m, 3H),7.73–7.75 (d, J=8.04 Hz, 2H), 7.89–7.91(t, J=3.60 Hz, 4H), 9.01 (s, 1H),12.91 (s, 1H). ESI-MS: m/z [M+H]⁺ 417.3.

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	0.19570 (14)	0.16142 (4)	0.64242 (3)	0.07526 (19)
S1	0.3284 (3)	0.41677 (8)	0.33059 (7)	0.0550 (4)
O1	0.2257 (8)	0.6333 (2)	−0.00717 (17)	0.0636 (9)
O2	0.2253 (9)	0.5689 (2)	0.25867 (18)	0.0687 (8)
N1	0.2711 (9)	0.6635 (2)	0.1388 (2)	0.0551 (12)
H1A	0.2352	0.7034	0.1931	0.066*
N3	0.5949 (10)	0.2787 (3)	0.1998 (2)	0.0621 (13)
N4	0.5645 (10)	0.2351 (2)	0.2632 (2)	0.0597 (8)
N2	0.4834 (9)	0.4276 (2)	0.1728 (2)	0.0539 (8)
H2A	0.5726	0.3992	0.1229	0.065*
C4	−0.2078 (13)	0.9136 (3)	0.0368 (3)	0.0711 (18)
H4B	−0.3108	0.9254	−0.0112	0.085*
C5	−0.0907 (12)	0.8176 (3)	0.0241 (3)	0.0610 (16)
H5A	−0.1231	0.7628	−0.0332	0.073*
C10	0.4756 (11)	0.3703 (3)	0.2263 (3)	0.0512 (11)
C16	0.1797 (12)	0.3039 (3)	0.5556 (3)	0.0632 (17)
H16A	0.0838	0.3486	0.6061	0.076*
C15	0.2691 (13)	0.2067 (3)	0.5481 (3)	0.0603 (10)
C12	0.3711 (10)	0.2674 (3)	0.4098 (2)	0.0471 (9)
C14	0.4058 (11)	0.1370 (3)	0.4729 (3)	0.0598 (11)
H14A	0.4596	0.0701	0.4688	0.072*
C17	0.2354 (12)	0.3345 (3)	0.4857 (3)	0.0587 (11)
H17A	0.1807	0.4014	0.4900	0.070*
C8	0.4114 (12)	0.5638 (3)	0.1200 (3)	0.0560 (15)
H8A	0.6486	0.5723	0.1144	0.067*
H8B	0.3068	0.5116	0.0627	0.067*
C9	0.3647 (11)	0.5237 (3)	0.1913 (2)	0.0475 (10)
C11	0.4297 (11)	0.2963 (3)	0.3341 (2)	0.0483 (10)
C13	0.4598 (12)	0.1698 (3)	0.4041 (3)	0.0601 (16)
H13A	0.5571	0.1253	0.3537	0.072*
C7	0.1970 (11)	0.6938 (3)	0.0722 (3)	0.0521 (13)
C6	0.0730 (11)	0.7991 (3)	0.0926 (2)	0.0489 (14)
C2	−0.0154 (12)	0.9776 (3)	0.1919 (3)	0.0601 (16)
H2B	0.0074	1.0320	0.2494	0.072*
C3	−0.1698 (12)	0.9930 (3)	0.1230 (3)	0.0643 (17)
H3B	−0.2533	1.0585	0.1332	0.077*
C1	0.1113 (12)	0.8805 (3)	0.1780 (3)	0.0555 (15)
H1B	0.2216	0.8701	0.2259	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0941 (4)	0.0888 (3)	0.0604 (2)	0.0226 (3)	0.0361 (2)	0.04206 (19)
S1	0.0804 (8)	0.0441 (5)	0.0406 (5)	0.0193 (5)	0.0286 (5)	0.0118 (4)
O1	0.106 (2)	0.0501 (14)	0.0414 (6)	0.0279 (14)	0.0433 (10)	0.0174 (7)
O2	0.1043 (12)	0.0616 (16)	0.0469 (7)	0.0256 (13)	0.0439 (6)	0.0207 (9)
N1	0.082 (3)	0.0452 (17)	0.0435 (16)	0.0255 (16)	0.0332 (18)	0.0165 (13)
N3	0.099 (3)	0.0488 (17)	0.0448 (17)	0.0288 (18)	0.0270 (19)	0.0193 (13)
N4	0.1059 (15)	0.0386 (15)	0.0399 (8)	0.0252 (12)	0.0297 (7)	0.0154 (8)
N2	0.075 (2)	0.0474 (5)	0.0474 (5)	0.0157 (15)	0.0353 (16)	0.0212 (3)
C4	0.097 (4)	0.049 (2)	0.070 (3)	0.025 (2)	0.022 (3)	0.022 (2)
C5	0.080 (3)	0.042 (2)	0.053 (2)	0.012 (2)	0.009 (2)	0.0102 (18)
C10	0.073 (3)	0.0390 (7)	0.0442 (7)	0.0091 (19)	0.024 (2)	0.0156 (4)
C16	0.080 (3)	0.054 (2)	0.051 (2)	0.012 (2)	0.034 (2)	0.0102 (19)
C15	0.0825 (16)	0.0564 (19)	0.0442 (9)	−0.0018 (12)	0.0194 (8)	0.0211 (8)
C12	0.0546 (15)	0.0498 (18)	0.0351 (9)	0.0036 (12)	0.0172 (7)	0.0131 (8)
C14	0.066 (2)	0.066 (2)	0.0600 (12)	0.0136 (14)	0.0282 (10)	0.0337 (10)
C17	0.078 (2)	0.050 (2)	0.0448 (11)	0.0131 (15)	0.0261 (10)	0.0109 (10)
C8	0.064 (3)	0.061 (2)	0.053 (2)	0.026 (2)	0.035 (2)	0.0269 (16)
C9	0.0644 (16)	0.041 (2)	0.0353 (8)	0.0082 (16)	0.0210 (7)	0.0104 (12)
C11	0.0753 (18)	0.0407 (18)	0.0336 (10)	0.0106 (14)	0.0223 (9)	0.0165 (9)
C13	0.094 (3)	0.042 (2)	0.046 (2)	0.010 (2)	0.030 (2)	0.0159 (16)
C7	0.071 (3)	0.047 (2)	0.0344 (7)	0.0104 (19)	0.0185 (14)	0.0105 (9)
C6	0.061 (3)	0.047 (2)	0.0339 (18)	0.0118 (19)	0.030 (2)	0.0067 (16)
C2	0.078 (3)	0.043 (2)	0.050 (2)	0.009 (2)	0.019 (2)	0.0062 (18)
C3	0.080 (3)	0.052 (2)	0.065 (3)	0.031 (2)	0.025 (3)	0.0211 (19)
C1	0.071 (3)	0.047 (2)	0.046 (2)	0.016 (2)	0.023 (2)	0.0120 (17)

Geometric parameters (Å, º) top

Br1—C15	1.898 (5)	C16—C17	1.382 (7)
S1—C10	1.714 (4)	C16—H16A	0.9300
S1—C11	1.741 (5)	C15—C14	1.387 (6)
O1—C7	1.242 (4)	C12—C13	1.370 (6)
O2—C9	1.214 (5)	C12—C17	1.380 (5)
N1—C7	1.323 (6)	C12—C11	1.461 (6)
N1—C8	1.430 (5)	C14—C13	1.383 (7)
N1—H1A	0.8600	C14—H14A	0.9300
N3—C10	1.285 (5)	C17—H17A	0.9300
N3—N4	1.387 (6)	C8—C9	1.483 (7)
N4—C11	1.299 (5)	C8—H8A	0.9700
N2—C9	1.349 (5)	C8—H8B	0.9700
N2—C10	1.381 (6)	C13—H13A	0.9300
N2—H2A	0.8600	C7—C6	1.469 (6)
C4—C5	1.361 (7)	C6—C1	1.383 (5)
C4—C3	1.382 (6)	C2—C3	1.335 (7)
C4—H4B	0.9300	C2—C1	1.388 (6)
C5—C6	1.367 (7)	C2—H2B	0.9300
C5—H5A	0.9300	C3—H3B	0.9300
C16—C15	1.359 (7)	C1—H1B	0.9300

C10—S1—C11	86.0 (2)	C16—C17—H17A	119.5
C7—N1—C8	119.6 (3)	N1—C8—C9	112.3 (3)
C7—N1—H1A	120.2	N1—C8—H8A	109.1
C8—N1—H1A	120.2	C9—C8—H8A	109.1
C10—N3—N4	110.7 (4)	N1—C8—H8B	109.1
C11—N4—N3	113.3 (3)	C9—C8—H8B	109.1
C9—N2—C10	126.3 (3)	H8A—C8—H8B	107.9
C9—N2—H2A	116.8	O2—C9—N2	121.9 (4)
C10—N2—H2A	116.8	O2—C9—C8	125.0 (4)
C5—C4—C3	118.3 (5)	N2—C9—C8	113.1 (3)
C5—C4—H4B	120.9	N4—C11—C12	123.3 (4)
C3—C4—H4B	120.9	N4—C11—S1	113.4 (3)
C4—C5—C6	122.2 (4)	C12—C11—S1	123.3 (3)
C4—C5—H5A	118.9	C12—C13—C14	120.4 (4)
C6—C5—H5A	118.9	C12—C13—H13A	119.8
N3—C10—N2	119.8 (4)	C14—C13—H13A	119.8
N3—C10—S1	116.5 (4)	O1—C7—N1	120.5 (4)
N2—C10—S1	123.6 (3)	O1—C7—C6	120.0 (4)
C15—C16—C17	118.0 (4)	N1—C7—C6	119.4 (3)
C15—C16—H16A	121.0	C5—C6—C1	118.3 (4)
C17—C16—H16A	121.0	C5—C6—C7	118.5 (3)
C16—C15—C14	122.6 (5)	C1—C6—C7	123.2 (4)
C16—C15—Br1	119.4 (3)	C3—C2—C1	120.2 (4)
C14—C15—Br1	118.0 (4)	C3—C2—H2B	119.9
C13—C12—C17	119.7 (4)	C1—C2—H2B	119.9
C13—C12—C11	117.6 (3)	C2—C3—C4	121.2 (4)
C17—C12—C11	122.6 (4)	C2—C3—H3B	119.4
C13—C14—C15	118.2 (4)	C4—C3—H3B	119.4
C13—C14—H14A	120.9	C6—C1—C2	119.8 (4)
C15—C14—H14A	120.9	C6—C1—H1B	120.1
C12—C17—C16	121.0 (4)	C2—C1—H1B	120.1
C12—C17—H17A	119.5

C10—N3—N4—C11	−1.0 (5)	C13—C12—C11—N4	−0.9 (6)
C3—C4—C5—C6	−2.5 (8)	C17—C12—C11—N4	178.3 (4)
N4—N3—C10—N2	179.7 (4)	C13—C12—C11—S1	179.6 (3)
N4—N3—C10—S1	2.2 (5)	C17—C12—C11—S1	−1.2 (6)
C9—N2—C10—N3	179.2 (4)	C10—S1—C11—N4	1.5 (3)
C9—N2—C10—S1	−3.6 (6)	C10—S1—C11—C12	−178.9 (4)
C11—S1—C10—N3	−2.2 (4)	C17—C12—C13—C14	1.8 (6)
C11—S1—C10—N2	−179.5 (4)	C11—C12—C13—C14	−179.0 (4)
C17—C16—C15—C14	−1.5 (7)	C15—C14—C13—C12	−1.8 (7)
C17—C16—C15—Br1	−179.8 (3)	C8—N1—C7—O1	5.2 (6)
C16—C15—C14—C13	1.7 (7)	C8—N1—C7—C6	−176.1 (4)
Br1—C15—C14—C13	−179.9 (3)	C4—C5—C6—C1	1.8 (7)
C13—C12—C17—C16	−1.6 (6)	C4—C5—C6—C7	−178.7 (5)
C11—C12—C17—C16	179.2 (4)	O1—C7—C6—C5	17.2 (7)
C15—C16—C17—C12	1.4 (7)	N1—C7—C6—C5	−161.5 (4)
C7—N1—C8—C9	−159.0 (4)	O1—C7—C6—C1	−163.3 (4)
C10—N2—C9—O2	−2.3 (6)	N1—C7—C6—C1	18.0 (7)
C10—N2—C9—C8	−180.0 (4)	C1—C2—C3—C4	0.1 (8)
N1—C8—C9—O2	−0.2 (6)	C5—C4—C3—C2	1.6 (8)
N1—C8—C9—N2	177.4 (3)	C5—C6—C1—C2	0.0 (7)
N3—N4—C11—C12	179.8 (4)	C7—C6—C1—C2	−179.5 (4)
N3—N4—C11—S1	−0.6 (5)	C3—C2—C1—C6	−0.9 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.93	2.49	3.400 (5)	168
N2—H2A···O1ⁱⁱ	0.86	1.99	2.835 (5)	167

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃BrN₄O₂S
M_r	417.28
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	4.020 (4), 13.706 (9), 16.210 (5)
α, β, γ (°)	113.334 (17), 94.018 (19), 92.78 (2)
V (Å³)	815.2 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.67
Crystal size (mm)	0.54 × 0.17 × 0.04

Data collection
Diffractometer	Bruker X8 APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.591, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	4633, 2592, 1097
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.109, 0.281, 0.82
No. of reflections	2592
No. of parameters	227
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.67, −1.40

Computer programs: , SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), APEX2 (Bruker, 2004) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.93	2.49	3.400 (5)	167.6
N2—H2A···O1ⁱⁱ	0.86	1.99	2.835 (5)	166.8

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

Footnotes

‡Additional correspondence author, e-mail: lishaohua0131@yahoo.com.cn.

Acknowledgements

The work was supported by the Science and Technology Research Project of JiangXi Provincial Educational Department (No. GJJ09076), the Science and Technology Planning Project of JiangXi Provincial Health Department (No. 20082015) and the Natural Science Foundation of JiangXi Province, China.

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