organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1158

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

aSchool of Pharmacy, Tianjin Medical University, Tianjin 300070, People's Republic of China, bMedical 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 29 March 2011; accepted 6 April 2011; online 16 April 2011)

In the title compound, C16H20N2O3, the crystal packing is stabilized by weak ππ stacking inter­actions [centroid–centroid distances = 3.577 (9) and 3.693 (9) Å] and inter­molecular C—H⋯O and N—H⋯O hydrogen-bond inter­actions. The C atoms of the N-isopropyl group are disordered over two sets of sites with occupancies of 0.61(3) and 0.39(3).

Related literature

For the biological activity of the title compound and its derivatives, see: Souli et al. (2008[Souli, E., Machluf, M., Morgenstern, A., Sabo, E. & Yannai, S. (2008). Food Chem. Toxicol. 46, 863-870.]); Chai et al. (2006[Chai, H. F., Zhao, Y. F., Zhao, C. S. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911-917.]); Radwan et al. (2007[Radwan, M. A. A., Ragab, E. A., Sabry, N. M. & El-Shenawy, S. M. (2007). Bioorg. Med. Chem. 15, 3832-3841.]); Karthikeyan et al. (2009[Karthikeyan, S. V., Perumal, S., Shetty, K. A., Yogeeswari, P. & Sriram, D. (2009). Bioorg. Med. Chem. Lett. 19, 3006-3009.]). For the preparation, see: Bacher et al. (2001[Bacher, G., Nickel, B., Emig, P., Vanhoefer, U., Seeber, S., Shandra, A., Klenner, T. & Becker, T. (2001). Cancer Res. 61, 392-399.]). For bond lengths and angles in similar structures, see: Feng et al. (2008[Feng, M., Zhao, M., Zhang, J., Yang, Z. & Chen, H. (2008). Acta Cryst. E64, o2339.]); Sonar et al. (2006[Sonar, V. N., Parkin, S. & Crooks, P. A. (2006). Acta Cryst. E62, o3744-o3746.]).

[Scheme 1]

Experimental

Crystal data
  • C16H20N2O3

  • Mr = 288.34

  • Orthorhombic, P b c a

  • a = 11.593 (3) Å

  • b = 9.182 (2) Å

  • c = 27.796 (6) Å

  • V = 2958.8 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 113 K

  • 0.30 × 0.24 × 0.10 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.974, Tmax = 0.991

  • 25486 measured reflections

  • 3527 independent reflections

  • 3320 reflections with I > 2σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.133

  • S = 1.12

  • 3527 reflections

  • 204 parameters

  • 39 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3A⋯O2i 0.95 2.54 3.4874 (17) 172
N2—H2B⋯O3ii 0.894 (19) 2.149 (19) 2.9933 (17) 157.2 (16)
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z].

Data collection: CrystalClear (Rigaku, 2005[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Indole and their derivatives are well known as substances with biologically activity such as anti-cancer (Souli et al., 2008), anti-virus (Chai et al., 2006), anti-tubercular (Karthikeyan et al., 2009), and anti-inflammatory (Radwan et al., 2007). In recent years, our recent study is paying attention to synthesize different kinds of indole derivatives with improved bioactivities. In this paper, we reported the crystal structure of the title compound.

In title compound, C16H20N2O3, bond lengths and angles are normal and in good agreement with those reported previously (Feng et al., 2008; Sonar, et al., 2006). ππ interactions are indicated by the short distance (Cg1···Cg2 distance of 3.693 (9) Å, Cg2···Cg2 distance of 3.577 (9)Å symmetry code: 1 - x,1 - y,-z) between the centroids of the pyrrole ring (N1/C1/C6—C8) (Cg1) and benzene ring C1—C6 (Cg2) (Table 1). There are weaker C—H···O and N—H···O intermolecular interactions, which stabilized the structure (Table 1).

Related literature top

For the biological activity of the title compound and its derivatives, see: Souli et al. (2008); Chai et al. (2006); Radwan et al. (2007); Karthikeyan et al. (2009). For the preparation, see: Bacher et al. (2001). For bond lengths and angles in similar structures, see: Feng et al. (2008); Sonar et al. (2006).

Experimental top

The target compound was synthesized by three steps. Under ice bath, DMF solution of 5-methoxy indole was added dropwise to DMF solution of NaH 0.5 h later, ethyl bromide was added. The reaction solvent add into ice water, and the compound is separated from the liquid after stirring. Oxalyl chloride was added dropwise to the 1-ethyl-methoxy indole in dry ether, 1-ethyl-methoxy indole-3-yl-glyoxyl chloride which was the crude product, propan-2-amine, two drops of triethylamine were in dry dichloromethane. The reaction mixture was washed with water and dried over Na2SO4 and concentrated in vacuo (Bacher et al., 2001). The residue was resolved in a methanol solution. Slow evaporatin over two week at room temperature gave light-yellow crystals suitable for X-ray analysis.

Refinement top

All C H atoms were found on difference maps, with C—H = 0.95–1.00 Å and H atoms bonded N were refined freely with N—H = 0.89 Å and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(C) for aryl and methylene H atoms and 1.5Ueq(C) for the methyl H atoms.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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
[Figure 1] Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 40% probability level.
2-(1-Ethyl-5-methoxy-1H-indol-3-yl)-N-isopropyl-2-oxoacetamide top
Crystal data top
C16H20N2O3F(000) = 1232
Mr = 288.34Dx = 1.295 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9914 reflections
a = 11.593 (3) Åθ = 1.9–27.9°
b = 9.182 (2) ŵ = 0.09 mm1
c = 27.796 (6) ÅT = 113 K
V = 2958.8 (11) Å3Prism, colorless
Z = 80.30 × 0.24 × 0.10 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
3527 independent reflections
Radiation source: rotating anode3320 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.053
Detector resolution: 14.63 pixels mm-1θmax = 27.9°, θmin = 1.5°
ω and ϕ scansh = 1415
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 129
Tmin = 0.974, Tmax = 0.991l = 3636
25486 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0661P)2 + 0.8297P]
where P = (Fo2 + 2Fc2)/3
3527 reflections(Δ/σ)max = 0.001
204 parametersΔρmax = 0.32 e Å3
39 restraintsΔρmin = 0.28 e Å3
Crystal data top
C16H20N2O3V = 2958.8 (11) Å3
Mr = 288.34Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.593 (3) ŵ = 0.09 mm1
b = 9.182 (2) ÅT = 113 K
c = 27.796 (6) Å0.30 × 0.24 × 0.10 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
3527 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
3320 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.991Rint = 0.053
25486 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04739 restraints
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.32 e Å3
3527 reflectionsΔρmin = 0.28 e Å3
204 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
xyzUiso*/UeqOcc. (<1)
O10.47198 (9)0.63365 (11)0.45512 (3)0.0265 (2)
O20.65875 (8)0.73051 (10)0.62010 (3)0.0242 (2)
O30.64406 (8)1.05760 (10)0.68489 (3)0.0233 (2)
N10.37396 (10)1.06105 (12)0.58694 (4)0.0201 (2)
N20.75248 (11)0.85420 (14)0.69650 (4)0.0247 (3)
C10.38287 (11)0.95977 (14)0.54960 (4)0.0188 (3)
C20.31491 (12)0.94441 (14)0.50881 (4)0.0208 (3)
H2A0.25111.00700.50310.025*
C30.34338 (11)0.83450 (15)0.47660 (5)0.0210 (3)
H3A0.29870.82110.44830.025*
C40.43820 (11)0.74299 (14)0.48577 (4)0.0200 (3)
C50.50502 (11)0.75732 (14)0.52708 (4)0.0198 (3)
H5A0.56810.69380.53300.024*
C60.47675 (11)0.86775 (14)0.55956 (4)0.0177 (3)
C70.52557 (11)0.91743 (14)0.60485 (4)0.0185 (3)
C80.45861 (11)1.03582 (14)0.61905 (4)0.0191 (3)
H8A0.47101.09110.64750.023*
C90.27776 (12)1.16154 (15)0.59397 (5)0.0244 (3)
H9A0.25641.20550.56270.029*
H9B0.30201.24110.61580.029*
C100.17353 (13)1.08439 (16)0.61518 (5)0.0284 (3)
H10A0.11051.15440.61940.043*
H10B0.19411.04250.64640.043*
H10C0.14871.00660.59340.043*
C110.40229 (13)0.60947 (16)0.41358 (5)0.0261 (3)
H11A0.43490.52950.39460.039*
H11B0.40030.69820.39400.039*
H11C0.32380.58410.42360.039*
C120.61865 (11)0.85066 (14)0.63061 (4)0.0180 (3)
C130.67303 (11)0.93253 (14)0.67372 (4)0.0189 (3)
C150.9362 (6)0.9639 (14)0.7211 (3)0.0447 (16)0.61 (3)
H15A0.92701.03230.69430.067*0.61 (3)
H15B0.98310.88090.71060.067*0.61 (3)
H15C0.97461.01320.74790.067*0.61 (3)
C140.81996 (14)0.91109 (16)0.73695 (5)0.0291 (3)0.61 (3)
H14A0.77770.99930.74850.035*0.61 (3)
C15'0.9489 (8)0.911 (2)0.7214 (5)0.048 (3)0.39 (3)
H15D0.95960.97790.69430.072*0.39 (3)
H15E0.97120.81220.71150.072*0.39 (3)
H15F0.99710.94180.74850.072*0.39 (3)
C14'0.81996 (14)0.91109 (16)0.73695 (5)0.0291 (3)0.39 (3)
H14B0.79351.01020.74700.035*0.39 (3)
C160.81764 (17)0.8043 (2)0.77817 (5)0.0408 (4)
H16A0.74050.79680.79070.049*
H16B0.84250.71080.76670.049*
H16C0.86850.83680.80270.049*
H2B0.7703 (15)0.765 (2)0.6858 (6)0.031 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0291 (5)0.0292 (5)0.0212 (5)0.0041 (4)0.0062 (4)0.0094 (4)
O20.0260 (5)0.0223 (5)0.0243 (5)0.0028 (4)0.0032 (4)0.0065 (4)
O30.0265 (5)0.0199 (5)0.0234 (5)0.0003 (4)0.0028 (4)0.0050 (4)
N10.0251 (6)0.0172 (5)0.0181 (5)0.0007 (4)0.0016 (4)0.0008 (4)
N20.0303 (6)0.0212 (6)0.0227 (5)0.0025 (5)0.0089 (5)0.0065 (5)
C10.0229 (6)0.0165 (6)0.0171 (6)0.0022 (5)0.0016 (5)0.0011 (5)
C20.0235 (7)0.0206 (6)0.0183 (6)0.0003 (5)0.0015 (5)0.0026 (5)
C30.0232 (7)0.0220 (6)0.0178 (6)0.0030 (5)0.0025 (5)0.0010 (5)
C40.0228 (6)0.0196 (6)0.0176 (6)0.0027 (5)0.0007 (5)0.0018 (5)
C50.0199 (6)0.0206 (6)0.0189 (6)0.0011 (5)0.0002 (5)0.0005 (5)
C60.0188 (6)0.0181 (6)0.0162 (5)0.0046 (5)0.0009 (4)0.0006 (5)
C70.0208 (6)0.0188 (6)0.0157 (5)0.0042 (5)0.0014 (4)0.0003 (5)
C80.0226 (6)0.0181 (6)0.0165 (6)0.0031 (5)0.0000 (5)0.0002 (5)
C90.0318 (7)0.0185 (6)0.0228 (6)0.0059 (5)0.0032 (5)0.0005 (5)
C100.0274 (7)0.0273 (7)0.0304 (7)0.0082 (6)0.0016 (6)0.0013 (6)
C110.0308 (7)0.0286 (7)0.0189 (6)0.0015 (6)0.0052 (5)0.0062 (5)
C120.0189 (6)0.0197 (6)0.0154 (5)0.0038 (5)0.0024 (4)0.0011 (4)
C130.0204 (6)0.0208 (6)0.0154 (5)0.0035 (5)0.0015 (5)0.0013 (4)
C150.053 (2)0.049 (4)0.0325 (17)0.027 (2)0.0132 (15)0.002 (2)
C140.0383 (8)0.0248 (7)0.0240 (7)0.0002 (6)0.0138 (6)0.0066 (5)
C15'0.051 (4)0.059 (6)0.035 (3)0.032 (4)0.009 (3)0.002 (4)
C14'0.0383 (8)0.0248 (7)0.0240 (7)0.0002 (6)0.0138 (6)0.0066 (5)
C160.0567 (11)0.0436 (10)0.0222 (7)0.0091 (8)0.0086 (7)0.0035 (6)
Geometric parameters (Å, º) top
O1—C41.3739 (15)C9—C101.520 (2)
O1—C111.4264 (16)C9—H9A0.9900
O2—C121.2323 (16)C9—H9B0.9900
O3—C131.2361 (16)C10—H10A0.9800
N1—C81.3465 (16)C10—H10B0.9800
N1—C11.3974 (16)C10—H10C0.9800
N1—C91.4606 (17)C11—H11A0.9800
N2—C131.3291 (18)C11—H11B0.9800
N2—C141.4659 (17)C11—H11C0.9800
N2—H2B0.894 (19)C12—C131.5487 (17)
C1—C21.3879 (18)C15—C141.499 (5)
C1—C61.4053 (18)C15—H15A0.9800
C2—C31.3888 (18)C15—H15B0.9800
C2—H2A0.9500C15—H15C0.9800
C3—C41.4069 (19)C14—C161.508 (2)
C3—H3A0.9500C14—H14A1.0000
C4—C51.3913 (18)C15'—H15D0.9800
C5—C61.3966 (17)C15'—H15E0.9800
C5—H5A0.9500C15'—H15F0.9800
C6—C71.4537 (17)C16—H16A0.9632
C7—C81.3928 (18)C16—H16B0.9595
C7—C121.4329 (18)C16—H16C0.9502
C8—H8A0.9500
C4—O1—C11117.02 (11)C9—C10—H10B109.5
C8—N1—C1108.90 (11)H10A—C10—H10B109.5
C8—N1—C9125.21 (11)C9—C10—H10C109.5
C1—N1—C9125.18 (11)H10A—C10—H10C109.5
C13—N2—C14122.84 (12)H10B—C10—H10C109.5
C13—N2—H2B119.8 (12)O1—C11—H11A109.5
C14—N2—H2B117.2 (12)O1—C11—H11B109.5
C2—C1—N1129.23 (12)H11A—C11—H11B109.5
C2—C1—C6122.64 (12)O1—C11—H11C109.5
N1—C1—C6108.12 (11)H11A—C11—H11C109.5
C1—C2—C3117.75 (12)H11B—C11—H11C109.5
C1—C2—H2A121.1O2—C12—C7123.27 (12)
C3—C2—H2A121.1O2—C12—C13117.68 (11)
C2—C3—C4120.19 (12)C7—C12—C13119.05 (11)
C2—C3—H3A119.9O3—C13—N2124.85 (12)
C4—C3—H3A119.9O3—C13—C12122.32 (12)
O1—C4—C5114.98 (12)N2—C13—C12112.83 (11)
O1—C4—C3123.14 (11)C14—C15—H15A109.5
C5—C4—C3121.88 (12)C14—C15—H15B109.5
C4—C5—C6118.12 (12)H15A—C15—H15B109.5
C4—C5—H5A120.9C14—C15—H15C109.5
C6—C5—H5A120.9H15A—C15—H15C109.5
C5—C6—C1119.40 (12)H15B—C15—H15C109.5
C5—C6—C7134.12 (12)N2—C14—C15111.7 (3)
C1—C6—C7106.47 (11)N2—C14—C16109.97 (12)
C8—C7—C12127.74 (11)C15—C14—C16116.8 (4)
C8—C7—C6105.86 (11)N2—C14—H14A105.9
C12—C7—C6126.28 (12)C15—C14—H14A105.9
N1—C8—C7110.65 (11)C16—C14—H14A105.9
N1—C8—H8A124.7H15D—C15'—H15E109.5
C7—C8—H8A124.7H15D—C15'—H15F109.5
N1—C9—C10111.38 (11)H15E—C15'—H15F109.5
N1—C9—H9A109.4C14—C16—H16A109.8
C10—C9—H9A109.4C14—C16—H16B109.0
N1—C9—H9B109.4H16A—C16—H16B109.6
C10—C9—H9B109.4C14—C16—H16C109.3
H9A—C9—H9B108.0H16A—C16—H16C109.7
C9—C10—H10A109.5H16B—C16—H16C109.5
C8—N1—C1—C2179.77 (13)C5—C6—C7—C125.2 (2)
C9—N1—C1—C29.5 (2)C1—C6—C7—C12175.99 (12)
C8—N1—C1—C60.47 (14)C1—N1—C8—C70.64 (15)
C9—N1—C1—C6170.26 (12)C9—N1—C8—C7170.09 (12)
N1—C1—C2—C3179.21 (12)C12—C7—C8—N1175.62 (12)
C6—C1—C2—C31.05 (19)C6—C7—C8—N10.54 (14)
C1—C2—C3—C40.07 (19)C8—N1—C9—C1092.41 (15)
C11—O1—C4—C5176.62 (12)C1—N1—C9—C1076.84 (16)
C11—O1—C4—C33.38 (19)C8—C7—C12—O2165.58 (13)
C2—C3—C4—O1179.06 (12)C6—C7—C12—O29.8 (2)
C2—C3—C4—C50.9 (2)C8—C7—C12—C1314.81 (19)
O1—C4—C5—C6179.04 (11)C6—C7—C12—C13169.78 (11)
C3—C4—C5—C60.96 (19)C14—N2—C13—O33.0 (2)
C4—C5—C6—C10.01 (18)C14—N2—C13—C12176.90 (12)
C4—C5—C6—C7178.74 (13)O2—C12—C13—O3174.90 (12)
C2—C1—C6—C51.04 (19)C7—C12—C13—O34.74 (18)
N1—C1—C6—C5179.18 (11)O2—C12—C13—N24.97 (17)
C2—C1—C6—C7179.92 (12)C7—C12—C13—N2175.39 (12)
N1—C1—C6—C70.13 (14)C13—N2—C14—C1597.9 (6)
C5—C6—C7—C8178.61 (14)C13—N2—C14—C16130.80 (15)
C1—C6—C7—C80.23 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···O2i0.952.543.4874 (17)172
N2—H2B···O3ii0.894 (19)2.149 (19)2.9933 (17)157.2 (16)
Cg1···Cg2iii3.693 (9)
Cg2···Cg2iii3.577 (9)
Symmetry codes: (i) x1/2, y+3/2, z+1; (ii) x+3/2, y1/2, z; (iii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC16H20N2O3
Mr288.34
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)113
a, b, c (Å)11.593 (3), 9.182 (2), 27.796 (6)
V3)2958.8 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.24 × 0.10
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.974, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
25486, 3527, 3320
Rint0.053
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.133, 1.12
No. of reflections3527
No. of parameters204
No. of restraints39
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.28

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···O2i0.952.543.4874 (17)172
N2—H2B···O3ii0.894 (19)2.149 (19)2.9933 (17)157.2 (16)
Cg1···Cg2iii..3.693 (9).
Cg2···Cg2iii..3.577 (9).
Symmetry codes: (i) x1/2, y+3/2, z+1; (ii) x+3/2, y1/2, z; (iii) x+1, y+1, z.
 

Acknowledgements

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

References

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Volume 67| Part 5| May 2011| Page o1158
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