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ISSN: 2056-9890

N-Acetyl-2-hy­droxy-N′-[meth­oxy(1-methylindol-2-yl)methyl]benzohydrazide

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 19 August 2008; accepted 20 August 2008; online 23 August 2008)

In the crystal structure of the title Schiff-base, C20H21N3O4, the amino group forms an N—H⋯O hydrogen bond to the acetyl group of an adjacent mol­ecule, forming a zigzag chain. The 2-hydr­oxy group is inter­nally hydrogen bonded to the amido group though an O—H⋯O hydrogen bond.

Related literature

For medicinal uses of the precursor Schiff base, see: Jin et al. (2006[Jin, L.-H., Chen, J., Song, B.-A., Chen, Z., Yang, S., Li, Q.-Z., Hu, D.-Y. & Xu, R.-Q. (2006). Bioorg. Med. Chem. Lett. 16, 5036-5040.]); Joshi et al. (2008[Joshi, S. D., Vagdevi, H. M., Vaidya, V. P. & Gadaginamath, G. S. (2008). Eur. J. Med. Chem. In the press.]); Szczepankiewicz et al. (2001[Szczepankiewicz, B. G., Liu, G., Jae, H.-S., Tasker, A. S., Gunawardana, I. W., von Geldern, T. W., Gwaltney, S. L., Wu-Wong, R., Gehrke, L., Chiou, W. J., Credo, R. B., Alder, J. D., Nukkala, M. A., Zielinski, N. A., Jarvis, K., Mollison, K. W., Frost, D. J., Bauch, J. L., Hui, Y. H., Claiborne, A. K., Li, Q. & Rosenberg, S. H. (2001). J. Med. Chem. 44, 4416-4430.]).

[Scheme 1]

Experimental

Crystal data
  • C20H21N3O4

  • Mr = 367.40

  • Monoclinic, P 21 /n

  • a = 11.0075 (3) Å

  • b = 10.5197 (3) Å

  • c = 15.4479 (4) Å

  • β = 93.967 (2)°

  • V = 1784.51 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 (2) K

  • 0.20 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 16316 measured reflections

  • 4072 independent reflections

  • 2646 reflections with I > 2σ(I)

  • Rint = 0.065

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.120

  • S = 1.02

  • 4072 reflections

  • 255 parameters

  • 2 restraints

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

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1o⋯O2 0.87 (1) 1.81 (2) 2.599 (2) 150 (3)
N1—H1n⋯O3i 0.85 (1) 2.01 (1) 2.812 (2) 157 (2)
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Comment top

The Schiff base, N'-[(1-methyl-1H-indol-2-yl)methylene]-2-hydroxybenzohydrazide, exhibits useful medicinal properties (Jin et al., 2006; Joshi et al., 2008; Szczepankiewicz et al., 2001). When dissolved in acetic anhydride, the compound undergoes a reaction to yield the title compound, (I), Fig. 1. Essentially, a mole of methyl acetate has been added across the carbon-nitrogen double-bond. In the crystal structure of (I), the amino group forms an N–H···O hydrogen bond to the acetyl group of an adjacent molecule to result in a zigzag chain that runs along the b-axis of the orthorhombic unit cell, Table 1. The 2-hydroxy group is internally hydrogen bonded to the amido group though an O–H···O hydrogen bond, Table 1.

Related literature top

For medicinal uses of the precursor Schiff base, see: Jin et al. (2006); Joshi et al. (2008); Szczepankiewicz et al. (2001).

Experimental top

2-Hydroxybenzohydrazide was condensed with 1-methylindole-3-carboxaldehyde to yield the corresponding Schiff base. To N'-[(1-methyl-1H-indol-2-yl)methylene]-2-hydroxybenzohydrazide (0.88 g, 3 mmol) was added acetic anhydride (10 ml). The mixture was heated to 398–403 K until the reactants dissolved completely. After 2 h of heating, the mixture was cooled and then treated with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated and the resulting solid was recrystallized from methanol to give (I) as colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C). The hydroxy- and ammonium H-atoms were located in a difference Fourier map, and were refined with a distance restraints O–H = N–H = 0.85±0.01 Å; their temperature factors were freely refined.

Computing details top

Data collection: APEX2 software (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (I) drawn at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
N-Acetyl-2-hydroxy-N'-[methoxy(1-methylindol-2- yl)methyl]benzohydrazide top
Crystal data top
C20H21N3O4F(000) = 776
Mr = 367.40Dx = 1.367 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1739 reflections
a = 11.0075 (3) Åθ = 2.2–21.4°
b = 10.5197 (3) ŵ = 0.10 mm1
c = 15.4479 (4) ÅT = 100 K
β = 93.967 (2)°Block, colorless
V = 1784.51 (8) Å30.20 × 0.15 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
2646 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
ω scansh = 1414
16316 measured reflectionsk = 1313
4072 independent reflectionsl = 2020
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) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0466P)2 + 0.3679P]
where P = (Fo2 + 2Fc2)/3
4072 reflections(Δ/σ)max = 0.001
255 parametersΔρmax = 0.26 e Å3
2 restraintsΔρmin = 0.26 e Å3
Crystal data top
C20H21N3O4V = 1784.51 (8) Å3
Mr = 367.40Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.0075 (3) ŵ = 0.10 mm1
b = 10.5197 (3) ÅT = 100 K
c = 15.4479 (4) Å0.20 × 0.15 × 0.10 mm
β = 93.967 (2)°
Data collection top
Bruker SMART APEX
diffractometer
2646 reflections with I > 2σ(I)
16316 measured reflectionsRint = 0.065
4072 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0472 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.26 e Å3
4072 reflectionsΔρmin = 0.26 e Å3
255 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.75833 (13)0.62701 (15)0.28349 (10)0.0328 (4)
H1O0.717 (2)0.5560 (16)0.2811 (18)0.069 (10)*
O20.57533 (11)0.47150 (13)0.28757 (9)0.0266 (3)
O30.27682 (12)0.25872 (13)0.22300 (9)0.0279 (3)
O40.41144 (11)0.35118 (13)0.43051 (8)0.0257 (3)
N10.38731 (14)0.55433 (15)0.29735 (10)0.0197 (4)
H1N0.3430 (17)0.6189 (15)0.3061 (14)0.037 (6)*
N20.33109 (13)0.43653 (14)0.29605 (10)0.0188 (3)
N30.12618 (13)0.52539 (15)0.40494 (10)0.0205 (4)
C10.68446 (17)0.7144 (2)0.31706 (12)0.0262 (5)
C20.73287 (19)0.8337 (2)0.33795 (14)0.0315 (5)
H20.81440.85300.32620.038*
C30.6634 (2)0.9230 (2)0.37533 (14)0.0354 (5)
H30.69721.00420.38920.042*
C40.54370 (19)0.8971 (2)0.39356 (13)0.0308 (5)
H40.49660.95920.42090.037*
C50.49478 (18)0.78036 (18)0.37132 (12)0.0249 (4)
H50.41320.76210.38370.030*
C60.56213 (17)0.68846 (18)0.33118 (12)0.0225 (4)
C70.51091 (17)0.56257 (18)0.30497 (11)0.0207 (4)
C80.31298 (16)0.36884 (19)0.22067 (12)0.0221 (4)
C90.33655 (19)0.4356 (2)0.13833 (13)0.0294 (5)
H9A0.30080.38670.08890.044*
H9B0.42460.44350.13370.044*
H9C0.29970.52040.13830.044*
C100.30451 (16)0.38509 (18)0.38166 (12)0.0212 (4)
H100.25040.30910.37360.025*
C110.24263 (16)0.48432 (18)0.43178 (12)0.0208 (4)
C120.28551 (17)0.55066 (18)0.50327 (12)0.0227 (4)
H120.36240.54000.53430.027*
C130.19310 (17)0.63891 (18)0.52267 (12)0.0222 (4)
C140.18300 (18)0.73351 (19)0.58605 (12)0.0261 (5)
H140.24740.74770.62910.031*
C150.07752 (18)0.8057 (2)0.58468 (13)0.0282 (5)
H150.07040.87080.62670.034*
C160.01854 (18)0.7841 (2)0.52232 (13)0.0295 (5)
H160.08990.83480.52300.035*
C170.01235 (17)0.6909 (2)0.45972 (13)0.0260 (5)
H170.07850.67540.41820.031*
C180.09490 (16)0.62076 (18)0.46006 (12)0.0220 (4)
C190.05096 (17)0.4838 (2)0.32897 (12)0.0269 (5)
H19A0.03510.48720.34150.040*
H19B0.07260.39630.31440.040*
H19C0.06470.53970.27990.040*
C200.4677 (2)0.24041 (19)0.39780 (14)0.0313 (5)
H20A0.53950.21830.43580.047*
H20B0.49240.25740.33920.047*
H20C0.40970.16960.39600.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0245 (7)0.0335 (9)0.0408 (9)0.0008 (7)0.0048 (6)0.0009 (7)
O20.0224 (7)0.0240 (8)0.0339 (8)0.0036 (6)0.0054 (6)0.0027 (6)
O30.0311 (8)0.0184 (8)0.0342 (8)0.0058 (6)0.0016 (6)0.0067 (6)
O40.0282 (7)0.0211 (8)0.0272 (7)0.0051 (6)0.0028 (6)0.0001 (6)
N10.0201 (8)0.0107 (8)0.0284 (9)0.0007 (7)0.0024 (7)0.0012 (7)
N20.0219 (8)0.0112 (8)0.0235 (8)0.0031 (6)0.0023 (6)0.0011 (7)
N30.0213 (8)0.0190 (9)0.0213 (8)0.0025 (7)0.0010 (6)0.0028 (7)
C10.0270 (10)0.0277 (12)0.0236 (10)0.0010 (9)0.0011 (8)0.0057 (9)
C20.0291 (11)0.0302 (12)0.0345 (12)0.0109 (10)0.0027 (9)0.0081 (10)
C30.0452 (13)0.0230 (12)0.0364 (12)0.0101 (10)0.0088 (10)0.0048 (10)
C40.0420 (13)0.0197 (11)0.0297 (11)0.0021 (9)0.0028 (10)0.0017 (9)
C50.0296 (10)0.0209 (11)0.0239 (10)0.0027 (9)0.0014 (8)0.0013 (9)
C60.0252 (10)0.0184 (10)0.0236 (10)0.0025 (8)0.0000 (8)0.0049 (8)
C70.0243 (10)0.0205 (10)0.0172 (9)0.0013 (8)0.0020 (7)0.0030 (8)
C80.0194 (9)0.0207 (11)0.0259 (10)0.0033 (8)0.0002 (8)0.0026 (8)
C90.0338 (11)0.0306 (12)0.0241 (10)0.0007 (10)0.0028 (9)0.0032 (9)
C100.0228 (9)0.0176 (10)0.0232 (10)0.0010 (8)0.0007 (8)0.0005 (8)
C110.0222 (9)0.0175 (10)0.0228 (9)0.0016 (8)0.0022 (8)0.0017 (8)
C120.0238 (10)0.0231 (11)0.0213 (9)0.0003 (8)0.0008 (8)0.0007 (8)
C130.0251 (10)0.0199 (10)0.0218 (10)0.0024 (8)0.0036 (8)0.0030 (8)
C140.0304 (11)0.0268 (12)0.0216 (10)0.0033 (9)0.0043 (8)0.0024 (9)
C150.0356 (11)0.0238 (11)0.0263 (10)0.0006 (9)0.0090 (9)0.0047 (9)
C160.0282 (11)0.0289 (12)0.0326 (11)0.0042 (9)0.0101 (9)0.0009 (10)
C170.0229 (10)0.0266 (11)0.0286 (11)0.0011 (8)0.0036 (8)0.0012 (9)
C180.0236 (9)0.0193 (10)0.0236 (10)0.0040 (8)0.0059 (8)0.0000 (8)
C190.0247 (10)0.0279 (12)0.0274 (11)0.0023 (9)0.0028 (8)0.0050 (9)
C200.0367 (12)0.0185 (11)0.0378 (12)0.0085 (9)0.0026 (10)0.0007 (9)
Geometric parameters (Å, º) top
O1—C11.354 (2)C8—C91.491 (3)
O1—H1O0.871 (10)C9—H9A0.9800
O2—C71.233 (2)C9—H9B0.9800
O3—C81.226 (2)C9—H9C0.9800
O4—C101.400 (2)C10—C111.492 (3)
O4—C201.428 (2)C10—H101.0000
N1—C71.360 (2)C11—C121.363 (3)
N1—N21.385 (2)C12—C131.424 (3)
N1—H1N0.852 (9)C12—H120.9500
N2—C81.368 (2)C13—C141.406 (3)
N2—C101.477 (2)C13—C181.413 (3)
N3—C181.375 (2)C14—C151.387 (3)
N3—C111.389 (2)C14—H140.9500
N3—C191.456 (2)C15—C161.399 (3)
C1—C21.393 (3)C15—H150.9500
C1—C61.406 (3)C16—C171.382 (3)
C2—C31.365 (3)C16—H160.9500
C2—H20.9500C17—C181.392 (3)
C3—C41.393 (3)C17—H170.9500
C3—H30.9500C19—H19A0.9800
C4—C51.375 (3)C19—H19B0.9800
C4—H40.9500C19—H19C0.9800
C5—C61.390 (3)C20—H20A0.9800
C5—H50.9500C20—H20B0.9800
C6—C71.485 (3)C20—H20C0.9800
C1—O1—H1O106.0 (19)O4—C10—C11107.19 (14)
C10—O4—C20112.71 (14)N2—C10—C11109.52 (15)
C7—N1—N2120.11 (16)O4—C10—H10109.6
C7—N1—H1N121.0 (15)N2—C10—H10109.6
N2—N1—H1N117.1 (15)C11—C10—H10109.6
C8—N2—N1121.13 (15)C12—C11—N3110.09 (17)
C8—N2—C10123.05 (15)C12—C11—C10129.33 (17)
N1—N2—C10115.52 (14)N3—C11—C10120.52 (16)
C18—N3—C11107.92 (15)C11—C12—C13106.97 (16)
C18—N3—C19124.45 (16)C11—C12—H12126.5
C11—N3—C19127.50 (16)C13—C12—H12126.5
O1—C1—C2118.06 (18)C14—C13—C18118.61 (18)
O1—C1—C6122.32 (18)C14—C13—C12134.43 (18)
C2—C1—C6119.6 (2)C18—C13—C12106.95 (17)
C3—C2—C1120.1 (2)C15—C14—C13118.93 (18)
C3—C2—H2119.9C15—C14—H14120.5
C1—C2—H2119.9C13—C14—H14120.5
C2—C3—C4121.1 (2)C14—C15—C16120.91 (19)
C2—C3—H3119.4C14—C15—H15119.5
C4—C3—H3119.4C16—C15—H15119.5
C5—C4—C3118.9 (2)C17—C16—C15121.71 (19)
C5—C4—H4120.5C17—C16—H16119.1
C3—C4—H4120.5C15—C16—H16119.1
C4—C5—C6121.40 (19)C16—C17—C18117.16 (18)
C4—C5—H5119.3C16—C17—H17121.4
C6—C5—H5119.3C18—C17—H17121.4
C5—C6—C1118.71 (18)N3—C18—C17129.29 (17)
C5—C6—C7122.54 (17)N3—C18—C13108.07 (16)
C1—C6—C7118.73 (18)C17—C18—C13122.64 (18)
O2—C7—N1121.25 (17)N3—C19—H19A109.5
O2—C7—C6122.64 (17)N3—C19—H19B109.5
N1—C7—C6116.05 (17)H19A—C19—H19B109.5
O3—C8—N2119.69 (18)N3—C19—H19C109.5
O3—C8—C9123.09 (18)H19A—C19—H19C109.5
N2—C8—C9117.21 (17)H19B—C19—H19C109.5
C8—C9—H9A109.5O4—C20—H20A109.5
C8—C9—H9B109.5O4—C20—H20B109.5
H9A—C9—H9B109.5H20A—C20—H20B109.5
C8—C9—H9C109.5O4—C20—H20C109.5
H9A—C9—H9C109.5H20A—C20—H20C109.5
H9B—C9—H9C109.5H20B—C20—H20C109.5
O4—C10—N2111.40 (15)
C7—N1—N2—C884.8 (2)N1—N2—C10—C1148.99 (19)
C7—N1—N2—C1089.2 (2)C18—N3—C11—C120.6 (2)
O1—C1—C2—C3177.23 (18)C19—N3—C11—C12176.65 (18)
C6—C1—C2—C32.8 (3)C18—N3—C11—C10176.91 (16)
C1—C2—C3—C40.2 (3)C19—N3—C11—C100.9 (3)
C2—C3—C4—C51.6 (3)O4—C10—C11—C1211.2 (3)
C3—C4—C5—C60.1 (3)N2—C10—C11—C12109.8 (2)
C4—C5—C6—C13.0 (3)O4—C10—C11—N3171.84 (16)
C4—C5—C6—C7178.81 (18)N2—C10—C11—N367.2 (2)
O1—C1—C6—C5175.68 (17)N3—C11—C12—C130.6 (2)
C2—C1—C6—C54.3 (3)C10—C11—C12—C13176.68 (18)
O1—C1—C6—C72.6 (3)C11—C12—C13—C14178.7 (2)
C2—C1—C6—C7177.42 (17)C11—C12—C13—C180.3 (2)
N2—N1—C7—O219.8 (3)C18—C13—C14—C150.2 (3)
N2—N1—C7—C6162.92 (15)C12—C13—C14—C15178.6 (2)
C5—C6—C7—O2163.41 (18)C13—C14—C15—C161.0 (3)
C1—C6—C7—O214.8 (3)C14—C15—C16—C170.2 (3)
C5—C6—C7—N119.4 (3)C15—C16—C17—C181.3 (3)
C1—C6—C7—N1162.41 (17)C11—N3—C18—C17179.76 (19)
N1—N2—C8—O3171.07 (16)C19—N3—C18—C174.0 (3)
C10—N2—C8—O32.5 (3)C11—N3—C18—C130.4 (2)
N1—N2—C8—C910.1 (2)C19—N3—C18—C13176.59 (17)
C10—N2—C8—C9176.32 (16)C16—C17—C18—N3178.60 (19)
C20—O4—C10—N271.2 (2)C16—C17—C18—C132.1 (3)
C20—O4—C10—C11168.97 (15)C14—C13—C18—N3179.21 (16)
C8—N2—C10—O4104.46 (19)C12—C13—C18—N30.1 (2)
N1—N2—C10—O469.42 (19)C14—C13—C18—C171.4 (3)
C8—N2—C10—C11137.13 (17)C12—C13—C18—C17179.47 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O20.87 (1)1.81 (2)2.599 (2)150 (3)
N1—H1n···O3i0.85 (1)2.01 (1)2.812 (2)157 (2)
Symmetry code: (i) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC20H21N3O4
Mr367.40
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)11.0075 (3), 10.5197 (3), 15.4479 (4)
β (°) 93.967 (2)
V3)1784.51 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.20 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16316, 4072, 2646
Rint0.065
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.120, 1.02
No. of reflections4072
No. of parameters255
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.26, 0.26

Computer programs: APEX2 software (Bruker, 2007), SAINT (Bruker, 2007), SAINT, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O20.87 (1)1.81 (2)2.599 (2)150 (3)
N1—H1n···O3i0.85 (1)2.01 (1)2.812 (2)157 (2)
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

We thank the University of Malaya for supporting this study (grant No. FS338/2008 A).

References

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First citationSzczepankiewicz, B. G., Liu, G., Jae, H.-S., Tasker, A. S., Gunawardana, I. W., von Geldern, T. W., Gwaltney, S. L., Wu-Wong, R., Gehrke, L., Chiou, W. J., Credo, R. B., Alder, J. D., Nukkala, M. A., Zielinski, N. A., Jarvis, K., Mollison, K. W., Frost, D. J., Bauch, J. L., Hui, Y. H., Claiborne, A. K., Li, Q. & Rosenberg, S. H. (2001). J. Med. Chem. 44, 4416–4430.  Web of Science CrossRef PubMed CAS Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

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