N-Cyclo­hexyl-2-(5-meth­oxy-1H-indol-3-yl)-2-oxoacetamide

Liu, J.; Liu, Y.-F.; Zhang, S.; Gao, Y.; Chen, H.

doi:10.1107/S1600536810054656

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o288

doi:10.1107/S1600536810054656

Open

access

N-Cyclohexyl-2-(5-methoxy-1H-indol-3-yl)-2-oxoacetamide

Jing Liu,^a Yong-Feng Liu,^b Shi Zhang,^b Ying Gao ^b and Hong Chen ^c ^*

^aSchool of Pharmacy, Tianjin Medical University, Tianjin 300070, People's Republic of China, ^bRoom of Pharmacognosy, Medical College of Chinese People's Armed Police Forces, Tianjin 300162, People's Republic of China, and ^cTianjin Key Laboratory for Biomarkers of Occupational and Environmental Hazards, Tianjin 300162, People's Republic of China
^*Correspondence e-mail: tjch2010@yahoo.cn

(Received 21 December 2010; accepted 29 December 2010; online 8 January 2011)

In the title compound, C₁₇H₂₀N₂O₃, the cyclohexane ring adopts a chair conformation. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into layers parallel to the ac plane.

Related literature

For the biological activity of indole derivatives, see: Souli et al. (2008 ); Chai et al. (2006 ); Radwan et al. (2007 ); Karthikeyan et al., (2009 ). For details of the synthesis, see: Bacher et al. (2001 ). For similar structures, see: Feng et al. (2008 ); Sonar et al. (2006 ).

Experimental

Crystal data

C₁₇H₂₀N₂O₃
M_r = 300.35
Monoclinic, P 2₁
a = 5.083 (3) Å
b = 27.336 (13) Å
c = 5.220 (3) Å
β = 91.977 (12)°
V = 724.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.981, T_max = 0.991
7342 measured reflections
1764 independent reflections
1569 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.076
S = 1.02
1764 reflections
208 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.96 (3)	1.90 (3)	2.840 (2)	164 (3)
N2—H2⋯O3ⁱⁱ	0.88 (3)	2.09 (3)	2.926 (3)	160 (3)
Symmetry codes: (i) x+1, y, z-1; (ii) x-1, y, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054656/cv5025sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054656/cv5025Isup2.hkl

checkCIF report

Comment top

Indole and their derivatives are well known as substances exhibiting various biological activiies, such as anti-cancer (Souli et al., 2008), anti-viral (Chai et al., 2006), anti-tubercular (Karthikeyan et al., 2009) and anti-inflammatory (Radwan et al., 2007). In our search for new indole derivatives with improved activities, we have synthesized the title compound, (I). Here we report its crystal structure.

In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Feng et al., 2008; Sonar et al., 2006). The cyclohexane ring (C12—C17) adopts a chair conformation. In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to the ac plane.

Related literature top

For the biological activity of indole derivatives, see: Souli et al. (2008); Chai et al. (2006); Radwan et al. (2007); Karthikeyan et al., (2009). For details of the synthesis, see: Bacher et al. (2001). For similar structures, see: Feng et al. (2008); Sonar et al. (2006).

Experimental top

The target compound was synthesized by two steps. Oxalyl chloride was added dropwise to a solution of 5-methoxy-indole in dry ether, the crude product 5-methoxyindol-3-yl-glyoxyl chloride, cyclohexylamine, two drops of triethylamine in dry dichloromethane. The reaction mixture was washed with water and dried over MgSO4 and concentrated in vacuo (Bacher et al., 2001). The residue was resolved in a methanol solution. Slow evaporation over two weeks at room temperature gave light-yellow crystals suitable for X-ray analysis.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 40% probability level.

N-Cyclohexyl-2-(5-methoxy-1H-indol-3-yl)-2-oxoacetamide top

Crystal data top

C₁₇H₂₀N₂O₃	F(000) = 320
M_r = 300.35	D_x = 1.376 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2636 reflections
a = 5.083 (3) Å	θ = 1.5–27.9°
b = 27.336 (13) Å	µ = 0.10 mm⁻¹
c = 5.220 (3) Å	T = 113 K
β = 91.977 (12)°	Prism, colourless
V = 724.9 (6) Å³	0.20 × 0.18 × 0.10 mm
Z = 2

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1764 independent reflections
Radiation source: rotating anode	1569 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.042
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 1.5°
ω and ϕ scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −36→31
T_min = 0.981, T_max = 0.991	l = −6→6
7342 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0439P)²] where P = (F_o² + 2F_c²)/3
1764 reflections	(Δ/σ)_max = 0.003
208 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₂₀N₂O₃	V = 724.9 (6) Å³
M_r = 300.35	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.083 (3) Å	µ = 0.10 mm⁻¹
b = 27.336 (13) Å	T = 113 K
c = 5.220 (3) Å	0.20 × 0.18 × 0.10 mm
β = 91.977 (12)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1764 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1569 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.991	R_int = 0.042
7342 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.23 e Å⁻³
1764 reflections	Δρ_min = −0.18 e Å⁻³
208 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. Along with the meaningless absolute structure parameter value (and s.u. value) obtained from any refinement with Friedel pairs, as justification of the merging of Friedel-pair data.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.1844 (3)	0.03318 (6)	0.3071 (3)	0.0242 (4)
O2	−0.1506 (3)	0.20016 (5)	0.8241 (3)	0.0181 (3)
O3	0.3519 (3)	0.28545 (6)	0.8311 (3)	0.0209 (4)
N1	0.4663 (4)	0.19176 (7)	0.2050 (3)	0.0175 (4)
N2	−0.0791 (4)	0.29907 (6)	0.8997 (3)	0.0167 (4)
C1	−0.3621 (4)	0.03287 (9)	0.5127 (5)	0.0241 (5)
H1A	−0.2627	0.0360	0.6761	0.036*
H1B	−0.4607	0.0021	0.5106	0.036*
H1C	−0.4851	0.0603	0.4927	0.036*
C2	−0.0281 (4)	0.07411 (8)	0.2854 (4)	0.0191 (5)
C3	0.1505 (4)	0.07156 (8)	0.0851 (4)	0.0207 (5)
H3	0.1508	0.0435	−0.0223	0.025*
C4	0.3242 (4)	0.10905 (8)	0.0430 (4)	0.0185 (4)
H4	0.4446	0.1075	−0.0920	0.022*
C5	0.3169 (4)	0.14924 (7)	0.2052 (4)	0.0158 (4)
C6	0.3895 (4)	0.22142 (8)	0.3936 (4)	0.0182 (4)
H6	0.4632	0.2526	0.4319	0.022*
C7	0.1850 (4)	0.19958 (8)	0.5251 (4)	0.0147 (4)
C8	0.1372 (4)	0.15268 (8)	0.4031 (4)	0.0153 (4)
C9	−0.0386 (4)	0.11418 (8)	0.4453 (4)	0.0170 (4)
H9	−0.1603	0.1156	0.5792	0.020*
C10	0.0403 (4)	0.22048 (7)	0.7283 (4)	0.0150 (4)
C11	0.1203 (4)	0.27147 (7)	0.8258 (4)	0.0154 (4)
C12	−0.0360 (4)	0.35000 (7)	0.9780 (4)	0.0168 (4)
H12	0.1085	0.3636	0.8739	0.020*
C13	−0.2834 (4)	0.38039 (8)	0.9209 (4)	0.0187 (4)
H13A	−0.4302	0.3675	1.0208	0.022*
H13B	−0.3340	0.3777	0.7366	0.022*
C14	−0.2356 (5)	0.43413 (8)	0.9899 (4)	0.0194 (5)
H14A	−0.4000	0.4529	0.9587	0.023*
H14B	−0.0995	0.4478	0.8793	0.023*
C15	−0.1453 (4)	0.43918 (8)	1.2721 (4)	0.0184 (4)
H15A	−0.1048	0.4739	1.3106	0.022*
H15B	−0.2888	0.4287	1.3832	0.022*
C16	0.0984 (4)	0.40803 (8)	1.3293 (4)	0.0205 (5)
H16A	0.1486	0.4106	1.5137	0.025*
H16B	0.2466	0.4206	1.2301	0.025*
C17	0.0493 (4)	0.35425 (8)	1.2602 (4)	0.0185 (5)
H17A	0.2123	0.3351	1.2934	0.022*
H17B	−0.0897	0.3408	1.3682	0.022*
H1	0.603 (6)	0.2006 (11)	0.090 (6)	0.042 (8)*
H2	−0.240 (5)	0.2875 (10)	0.891 (5)	0.027 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0251 (8)	0.0167 (8)	0.0310 (9)	−0.0030 (7)	0.0032 (7)	−0.0044 (7)
O2	0.0158 (7)	0.0174 (8)	0.0214 (8)	−0.0014 (6)	0.0052 (6)	−0.0016 (6)
O3	0.0157 (7)	0.0193 (8)	0.0277 (9)	−0.0012 (6)	0.0022 (6)	−0.0038 (6)
N1	0.0182 (9)	0.0182 (9)	0.0167 (9)	0.0019 (7)	0.0070 (7)	−0.0002 (7)
N2	0.0132 (9)	0.0159 (9)	0.0211 (10)	−0.0008 (7)	0.0020 (7)	−0.0023 (7)
C1	0.0225 (12)	0.0194 (11)	0.0303 (13)	−0.0028 (10)	0.0008 (10)	0.0029 (9)
C2	0.0180 (11)	0.0165 (11)	0.0226 (11)	0.0014 (8)	−0.0016 (9)	−0.0004 (8)
C3	0.0249 (12)	0.0198 (11)	0.0171 (11)	0.0046 (9)	−0.0033 (9)	−0.0045 (9)
C4	0.0190 (10)	0.0210 (12)	0.0155 (10)	0.0043 (9)	0.0015 (8)	−0.0021 (8)
C5	0.0169 (10)	0.0169 (10)	0.0137 (10)	0.0016 (8)	0.0016 (8)	0.0023 (8)
C6	0.0183 (10)	0.0175 (11)	0.0189 (10)	0.0013 (9)	0.0011 (8)	0.0005 (8)
C7	0.0133 (9)	0.0139 (10)	0.0168 (10)	0.0014 (8)	0.0012 (8)	0.0007 (8)
C8	0.0128 (10)	0.0176 (10)	0.0155 (10)	0.0027 (8)	0.0008 (8)	0.0006 (8)
C9	0.0160 (10)	0.0179 (11)	0.0171 (10)	0.0005 (9)	0.0017 (8)	0.0031 (8)
C10	0.0144 (10)	0.0138 (10)	0.0169 (10)	0.0016 (8)	0.0003 (8)	0.0007 (8)
C11	0.0163 (10)	0.0159 (11)	0.0141 (10)	−0.0001 (8)	0.0025 (8)	0.0006 (8)
C12	0.0173 (10)	0.0137 (10)	0.0196 (11)	0.0004 (8)	0.0028 (9)	−0.0011 (8)
C13	0.0197 (10)	0.0164 (10)	0.0200 (11)	0.0005 (9)	0.0019 (9)	−0.0015 (8)
C14	0.0204 (11)	0.0154 (10)	0.0225 (11)	0.0022 (8)	0.0035 (9)	0.0023 (8)
C15	0.0199 (11)	0.0148 (10)	0.0209 (11)	0.0004 (8)	0.0053 (9)	−0.0024 (8)
C16	0.0227 (11)	0.0195 (11)	0.0194 (11)	0.0010 (9)	0.0011 (9)	−0.0013 (8)
C17	0.0199 (11)	0.0174 (11)	0.0182 (11)	0.0038 (9)	0.0001 (9)	−0.0015 (8)

Geometric parameters (Å, º) top

O1—C2	1.379 (3)	C7—C10	1.431 (3)
O1—C1	1.427 (3)	C7—C8	1.448 (3)
O2—C10	1.238 (2)	C8—C9	1.403 (3)
O3—C11	1.237 (2)	C9—H9	0.9500
N1—C6	1.344 (3)	C10—C11	1.534 (3)
N1—C5	1.389 (3)	C12—C17	1.526 (3)
N1—H1	0.96 (3)	C12—C13	1.528 (3)
N2—C11	1.331 (3)	C12—H12	1.0000
N2—C12	1.465 (3)	C13—C14	1.530 (3)
N2—H2	0.88 (3)	C13—H13A	0.9900
C1—H1A	0.9800	C13—H13B	0.9900
C1—H1B	0.9800	C14—C15	1.534 (3)
C1—H1C	0.9800	C14—H14A	0.9900
C2—C9	1.379 (3)	C14—H14B	0.9900
C2—C3	1.409 (3)	C15—C16	1.524 (3)
C3—C4	1.375 (3)	C15—H15A	0.9900
C3—H3	0.9500	C15—H15B	0.9900
C4—C5	1.388 (3)	C16—C17	1.532 (3)
C4—H4	0.9500	C16—H16A	0.9900
C5—C8	1.405 (3)	C16—H16B	0.9900
C6—C7	1.399 (3)	C17—H17A	0.9900
C6—H6	0.9500	C17—H17B	0.9900

C2—O1—C1	116.63 (17)	O3—C11—N2	123.5 (2)
C6—N1—C5	109.37 (18)	O3—C11—C10	121.94 (18)
C6—N1—H1	122.6 (18)	N2—C11—C10	114.56 (18)
C5—N1—H1	128.1 (18)	N2—C12—C17	112.11 (17)
C11—N2—C12	120.74 (17)	N2—C12—C13	110.36 (18)
C11—N2—H2	119.9 (18)	C17—C12—C13	110.58 (17)
C12—N2—H2	119.2 (18)	N2—C12—H12	107.9
O1—C1—H1A	109.5	C17—C12—H12	107.9
O1—C1—H1B	109.5	C13—C12—H12	107.9
H1A—C1—H1B	109.5	C12—C13—C14	110.68 (18)
O1—C1—H1C	109.5	C12—C13—H13A	109.5
H1A—C1—H1C	109.5	C14—C13—H13A	109.5
H1B—C1—H1C	109.5	C12—C13—H13B	109.5
C9—C2—O1	124.05 (18)	C14—C13—H13B	109.5
C9—C2—C3	121.8 (2)	H13A—C13—H13B	108.1
O1—C2—C3	114.11 (19)	C13—C14—C15	110.64 (18)
C4—C3—C2	121.0 (2)	C13—C14—H14A	109.5
C4—C3—H3	119.5	C15—C14—H14A	109.5
C2—C3—H3	119.5	C13—C14—H14B	109.5
C3—C4—C5	117.46 (19)	C15—C14—H14B	109.5
C3—C4—H4	121.3	H14A—C14—H14B	108.1
C5—C4—H4	121.3	C16—C15—C14	110.60 (18)
C4—C5—N1	129.47 (18)	C16—C15—H15A	109.5
C4—C5—C8	122.22 (19)	C14—C15—H15A	109.5
N1—C5—C8	108.29 (18)	C16—C15—H15B	109.5
N1—C6—C7	109.98 (19)	C14—C15—H15B	109.5
N1—C6—H6	125.0	H15A—C15—H15B	108.1
C7—C6—H6	125.0	C15—C16—C17	111.42 (19)
C6—C7—C10	127.11 (19)	C15—C16—H16A	109.3
C6—C7—C8	106.15 (17)	C17—C16—H16A	109.3
C10—C7—C8	126.63 (17)	C15—C16—H16B	109.3
C9—C8—C5	119.91 (19)	C17—C16—H16B	109.3
C9—C8—C7	133.89 (18)	H16A—C16—H16B	108.0
C5—C8—C7	106.20 (18)	C12—C17—C16	109.81 (17)
C2—C9—C8	117.55 (18)	C12—C17—H17A	109.7
C2—C9—H9	121.2	C16—C17—H17A	109.7
C8—C9—H9	121.2	C12—C17—H17B	109.7
O2—C10—C7	123.40 (19)	C16—C17—H17B	109.7
O2—C10—C11	118.42 (18)	H17A—C17—H17B	108.2
C7—C10—C11	118.15 (17)

C1—O1—C2—C9	−1.3 (3)	C5—C8—C9—C2	−0.7 (3)
C1—O1—C2—C3	177.67 (19)	C7—C8—C9—C2	179.7 (2)
C9—C2—C3—C4	0.6 (3)	C6—C7—C10—O2	174.9 (2)
O1—C2—C3—C4	−178.4 (2)	C8—C7—C10—O2	−0.7 (3)
C2—C3—C4—C5	0.1 (3)	C6—C7—C10—C11	−2.9 (3)
C3—C4—C5—N1	−179.4 (2)	C8—C7—C10—C11	−178.55 (19)
C3—C4—C5—C8	−1.2 (3)	C12—N2—C11—O3	4.1 (3)
C6—N1—C5—C4	178.7 (2)	C12—N2—C11—C10	−175.09 (18)
C6—N1—C5—C8	0.3 (2)	O2—C10—C11—O3	148.5 (2)
C5—N1—C6—C7	−0.2 (2)	C7—C10—C11—O3	−33.6 (3)
N1—C6—C7—C10	−176.2 (2)	O2—C10—C11—N2	−32.4 (3)
N1—C6—C7—C8	0.1 (2)	C7—C10—C11—N2	145.54 (19)
C4—C5—C8—C9	1.5 (3)	C11—N2—C12—C17	−85.5 (2)
N1—C5—C8—C9	−179.95 (19)	C11—N2—C12—C13	150.80 (19)
C4—C5—C8—C7	−178.77 (19)	N2—C12—C13—C14	−177.23 (17)
N1—C5—C8—C7	−0.2 (2)	C17—C12—C13—C14	58.2 (2)
C6—C7—C8—C9	179.8 (2)	C12—C13—C14—C15	−56.8 (2)
C10—C7—C8—C9	−3.9 (4)	C13—C14—C15—C16	55.7 (2)
C6—C7—C8—C5	0.1 (2)	C14—C15—C16—C17	−56.4 (2)
C10—C7—C8—C5	176.4 (2)	N2—C12—C17—C16	178.52 (17)
O1—C2—C9—C8	178.57 (19)	C13—C12—C17—C16	−57.9 (2)
C3—C2—C9—C8	−0.4 (3)	C15—C16—C17—C12	57.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.96 (3)	1.90 (3)	2.840 (2)	164 (3)
N2—H2···O3ⁱⁱ	0.88 (3)	2.09 (3)	2.926 (3)	160 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂O₃
M_r	300.35
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	113
a, b, c (Å)	5.083 (3), 27.336 (13), 5.220 (3)
β (°)	91.977 (12)
V (Å³)	724.9 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.981, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	7342, 1764, 1569
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.076, 1.02
No. of reflections	1764
No. of parameters	208
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: CrystalClear (Rigaku, 2005), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.96 (3)	1.90 (3)	2.840 (2)	164 (3)
N2—H2···O3ⁱⁱ	0.88 (3)	2.09 (3)	2.926 (3)	160 (3)

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 30873363), the Program of the Science Foundation of Tianjin (grant No. 08JCYBJC070000) and the Major Program of the Science Foundation of Tianjin (grant No. 09ZCKFSH01700).

References

Bacher, G., Nickel, B., Emig, P., Vanhoefer, U., Seeber, S., Shandra, A., Klenner, T. & Becker, T. (2001). Cancer Res. 61, 392–399. Web of Science PubMed CAS Google Scholar
Chai, H. F., Zhao, Y. F., Zhao, C. S. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911–917. Web of Science CrossRef PubMed CAS Google Scholar
Feng, M., Zhao, M., Zhang, J., Yang, Z. & Chen, H. (2008). Acta Cryst. E64, o2339. Web of Science CSD CrossRef IUCr Journals Google Scholar
Karthikeyan, S. V., Perumal, S., Shetty, K. A., Yogeeswari, P. & Sriram, D. (2009). Bioorg. Med. Chem. Lett. 19, 3006–3009. Web of Science CrossRef PubMed CAS Google Scholar
Radwan, M. A. A., Ragab, E. A., Sabry, N. M. & El-Shenawy, S. M. (2007). Bioorg. Med. Chem. 15, 3832–3841. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sonar, V. N., Parkin, S. & Crooks, P. A. (2006). Acta Cryst. E62, o3744–o3746. Web of Science CSD CrossRef IUCr Journals Google Scholar
Souli, E., Machluf, M., Morgenstern, A., Sabo, E. & Yannai, S. (2008). Food Chem. Toxicol. 46, 863–870. Web of Science CrossRef PubMed CAS Google Scholar