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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Di­ethyl 2-[(3,5-di­methyl-1H-pyrazol-1-yl)(4-meth­­oxy­phen­yl)meth­yl]propane­dioate

aLaboratoire de Chimie Organique, Faculté des Sciences Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, bLaboratoire de Chimie de Coordination, 205 Route de Narbonne, 31077 Toulouse Cedex, France, and cLaboratoires de Diffraction des Rayons X, Division UATRS, Centre National pour la Recherche Scientifique et Technique, Rabat, Morocco
*Correspondence e-mail: daoudimaria@yahoo.fr

(Received 26 June 2010; accepted 29 June 2010; online 10 July 2010)

The title compound, C20H26N2O5, was prepared in good yield (76%) through condensation of diethyl (4-meth­oxy­benz­yl)propane­dioate with 3,5-dimethyl-1H-pyrazole. The dihedral between the benzene and pyrazole rings is 83.96 (10)°. The crystal packing is stabilized by a C—H⋯O inter­action, which links the mol­ecules into centrosymmetric dimers.

Related literature

For related compounds displaying biological activity, see: Dayam et al. (2007[Dayam, R., Al-Mawsawi, L. Q. & Neamati, N. (2007). Bioorg. Med. Chem. Lett. 17, 6155-6159.]); Patil et al. (2007[Patil, S., Kamath, S., Sanchez, T., Neamati, N., Schinazi, R. F. & Buolamwini, J. K. (2007). Bioorg. Med. Chem. 15, 1212-1228.]); Ramkumar et al. (2008[Ramkumar, K., Tambov, K. V., Gundla, R., Manaev, A. V., Yarovenko, V., Traven, V. F. & Neamati, N. (2008). Bioorg. Med. Chem. 16, 8988-8998.]); Sechi et al. (2009[Sechi, M., Carta, F., Sannia, L., Dallocchio, R., Dessì, A., Al-Safi, R. I. & Neamati, N. (2009). Antiviral Res. 81, 267-276.]) & Zeng et al. (2008[Zeng, L. F., Zhang, H.-S. W., ang, Y. H., Sanchez, T., Zheng, Y. T., Neamati, N. & Long, Y. Q. (2008). Bioorg. Med. Chem. Lett. 18, 4521-4524.]). For the synthetic procedure, see: Pommier & Neamati (2006[Pommier, Y. & Neamati, N. (2006). Bioorg. Med. Chem. 14, 3785-3792.]).

[Scheme 1]

Experimental

Crystal data
  • C20H26N2O5

  • Mr = 374.43

  • Monoclinic, P 21 /c

  • a = 11.9618 (3) Å

  • b = 7.9681 (2) Å

  • c = 21.1269 (6) Å

  • β = 96.504 (1)°

  • V = 2000.70 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.23 × 0.17 × 0.14 mm

Data collection
  • Bruker X8 APEXII CCD area-detector diffractometer

  • 18616 measured reflections

  • 3921 independent reflections

  • 3177 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.154

  • S = 1.05

  • 3921 reflections

  • 249 parameters

  • H-atom parameters constrained

  • Δρmax = 0.68 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12⋯O2i 0.93 2.51 3.358 (3) 152
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

For the rational design of new HIV-1 Integrase (H—I) inhibitors, one validated target for chemotherapeutic intervention (Dayam et al., 2007), is fundamentally based on intermolecular coordination between H—I / chemical inhibitor / metals (Mg+2 and Mn+2, co-factors of the enzyme), leading to the formation of bimetallic complexes (Zeng et al., 2008; Sechi et al., 2009). Thereby, several bimetallic metal complexes, in many cases exploring the known-well polydentate ligands, appear in this scenario as the most promising concept to be employed in either enzyme / drug interaction or electron transfer process, in the last case involving the biological oxygen transfer (Sechi et al., 2009; Ramkumar et al., 2008). Another exciting example of application for such polydentate ligands involves the synergic water activation, that occurs via the so-called -remote metallic atoms. Such organometallic compounds are structurally deemed to promote or block the H—I activity (Zeng et al., 2008).

In the molecule of the title compound (Fig.1), the dihedral angle between the planes of the pheny and the pyrazol ring is 83.96 (10)°.

Related literature top

For related compounds displaying biological activity, see: Dayam et al. (2007); Patil et al. (2007); Ramkumar et al. (2008); Sechi et al. (2009) & Zeng et al. (2008). For the synthetic procedure, see: Pommier & Neamati (2006).

Experimental top

To a solution of the diethyl (4-methoxybenzyl)propanedioate (5 mmol) in water (20 ml) was added the 3,5-dimethyl-1H-pyrazole (6 mmol) and the mixture and the stirring was continued at room temperature until the complete consume of the starting material. After removing solvent, the crude products were dissolved in diethyl ether (2x40 ml) and washed with water until the pH became neutral. The organic solvent was dried with sodium sulfate and then evaporated to give the pure compound (I) with 76% yield.. White crystals are obtained by recrystallization in ether/hexane (2/1).

Suitable single-crystal of malonate derivative (I) was obtained by recrystallization from ethanol. A white-transparent crystal was mounted on a glass fibre.

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.96 Å (methyl), C—H = 0.93 Å (aromatic), 0.97 Å (methylene) and 0.98 Å (methine) with Uiso(H) = 1.2Ueq or Uiso(H) = 1.5Ueq(methyl).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Partial packing view showing the chain generated by C—H···O hydrogen bonds shown as dashed lines. Symmetry code for generating the second molecule: 1 - x,-y,1 - z.
[Figure 3] Fig. 3. View of the title compound showing displacement ellipsoids at the 50% probability level.
Diethyl 2-[(3,5-dimethyl-1H-pyrazol-1-yl)(4-methoxyphenyl)methyl]propanedioate top
Crystal data top
C20H26N2O5F(000) = 800
Mr = 374.43Dx = 1.243 Mg m3
Monoclinic, P21/cMelting point: 361 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.9618 (3) ÅCell parameters from 2174 reflections
b = 7.9681 (2) Åθ = 2.3–27.1°
c = 21.1269 (6) ŵ = 0.09 mm1
β = 96.504 (1)°T = 296 K
V = 2000.70 (9) Å3Block, colourless
Z = 40.23 × 0.17 × 0.14 mm
Data collection top
Bruker X8 APEXII CCD area-detector
diffractometer
3177 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 26.0°, θmin = 2.7°
ϕ and ω scansh = 1414
18616 measured reflectionsk = 99
3921 independent reflectionsl = 2626
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0687P)2 + 1.8319P]
where P = (Fo2 + 2Fc2)/3
3921 reflections(Δ/σ)max = 0.007
249 parametersΔρmax = 0.68 e Å3
0 restraintsΔρmin = 0.45 e Å3
Crystal data top
C20H26N2O5V = 2000.70 (9) Å3
Mr = 374.43Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.9618 (3) ŵ = 0.09 mm1
b = 7.9681 (2) ÅT = 296 K
c = 21.1269 (6) Å0.23 × 0.17 × 0.14 mm
β = 96.504 (1)°
Data collection top
Bruker X8 APEXII CCD area-detector
diffractometer
3177 reflections with I > 2σ(I)
18616 measured reflectionsRint = 0.027
3921 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 1.05Δρmax = 0.68 e Å3
3921 reflectionsΔρmin = 0.45 e Å3
249 parameters
Special details top

Experimental. The data collection nominally covered a sphere of reciprocal space, by a combination of tree sets of exposures; each set had a different ϕ angle for the crystal and each exposure covered 0.5° in ω and 20 s in time. The crystal-to-detector distance was 37.5 mm.

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*/Ueq
O20.40914 (11)0.14261 (19)0.44322 (7)0.0301 (3)
O30.26937 (12)0.19794 (18)0.36564 (7)0.0321 (4)
O40.39768 (14)0.2442 (2)0.36381 (8)0.0441 (4)
O50.23951 (15)0.1580 (2)0.30637 (7)0.0446 (4)
O10.16987 (15)0.2065 (2)0.68944 (8)0.0468 (5)
N10.25069 (14)0.3219 (2)0.47437 (8)0.0252 (4)
N20.15274 (14)0.3525 (2)0.43620 (8)0.0297 (4)
C10.29918 (16)0.1528 (2)0.47752 (9)0.0230 (4)
H10.38130.16330.48450.028*
C20.26772 (16)0.0673 (3)0.41296 (9)0.0244 (4)
H20.18590.05410.40510.029*
C110.26097 (16)0.0542 (2)0.53261 (9)0.0229 (4)
C30.32439 (16)0.1032 (2)0.41081 (9)0.0239 (4)
C120.33950 (17)0.0251 (3)0.57616 (9)0.0277 (4)
H120.41540.01970.57060.033*
C210.28468 (17)0.4563 (3)0.51094 (10)0.0285 (5)
C160.14790 (16)0.0419 (3)0.54174 (10)0.0277 (4)
H160.09410.09290.51270.033*
C130.30680 (18)0.1116 (3)0.62736 (10)0.0323 (5)
H130.36050.16430.65590.039*
C140.19347 (18)0.1206 (3)0.63658 (10)0.0311 (5)
C150.11364 (17)0.0445 (3)0.59307 (10)0.0312 (5)
H150.03760.05150.59830.037*
C60.30985 (19)0.1697 (3)0.35912 (10)0.0308 (5)
C230.12710 (18)0.5105 (3)0.44907 (11)0.0322 (5)
C40.32363 (19)0.3556 (3)0.35159 (12)0.0370 (5)
H4A0.26790.43290.33140.044*
H4B0.35750.40630.39090.044*
C220.20634 (18)0.5797 (3)0.49546 (10)0.0330 (5)
H220.20600.68740.51240.040*
C50.4121 (2)0.3243 (4)0.30837 (11)0.0466 (6)
H5A0.37890.26930.27040.070*
H5B0.44420.42920.29730.070*
H5C0.46990.25420.32960.070*
C250.3888 (2)0.4563 (3)0.55689 (12)0.0416 (6)
H25A0.37430.40000.59530.062*
H25B0.41140.56990.56660.062*
H25C0.44780.39900.53840.062*
C70.2781 (3)0.2351 (4)0.24975 (12)0.0612 (8)
H7A0.26950.35600.25150.073*
H7B0.35710.20980.24810.073*
C240.0258 (2)0.5924 (3)0.41410 (14)0.0489 (7)
H24A0.04930.67220.38420.073*
H24B0.01600.64900.44390.073*
H24C0.02090.50860.39170.073*
C170.0566 (2)0.2040 (4)0.70479 (13)0.0545 (7)
H17A0.03350.09000.71010.082*
H17B0.05210.26490.74360.082*
H17C0.00810.25540.67090.082*
C80.2127 (3)0.1700 (5)0.19471 (13)0.0731 (10)
H8A0.22450.05110.19220.110*
H8B0.23510.22300.15730.110*
H8C0.13450.19190.19750.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0249 (7)0.0292 (8)0.0357 (8)0.0049 (6)0.0007 (6)0.0048 (6)
O30.0317 (8)0.0265 (8)0.0371 (8)0.0009 (6)0.0005 (6)0.0089 (6)
O40.0466 (10)0.0436 (10)0.0435 (9)0.0125 (8)0.0117 (8)0.0046 (8)
O50.0624 (11)0.0441 (10)0.0264 (8)0.0085 (8)0.0010 (7)0.0036 (7)
O10.0475 (10)0.0586 (12)0.0360 (9)0.0031 (9)0.0117 (7)0.0143 (8)
N10.0258 (8)0.0229 (9)0.0265 (8)0.0027 (7)0.0013 (7)0.0005 (7)
N20.0280 (9)0.0278 (9)0.0330 (9)0.0061 (7)0.0015 (7)0.0008 (7)
C10.0216 (9)0.0196 (9)0.0277 (10)0.0025 (7)0.0022 (7)0.0011 (8)
C20.0221 (9)0.0238 (10)0.0273 (10)0.0019 (8)0.0031 (8)0.0012 (8)
C110.0242 (9)0.0203 (10)0.0246 (9)0.0011 (8)0.0036 (7)0.0037 (7)
C30.0230 (10)0.0237 (10)0.0257 (9)0.0028 (8)0.0067 (8)0.0018 (8)
C120.0228 (10)0.0311 (11)0.0287 (10)0.0005 (8)0.0009 (8)0.0014 (8)
C210.0320 (11)0.0253 (11)0.0294 (10)0.0012 (8)0.0088 (8)0.0025 (8)
C160.0242 (10)0.0293 (11)0.0292 (10)0.0060 (8)0.0014 (8)0.0008 (8)
C130.0315 (11)0.0372 (13)0.0268 (10)0.0019 (9)0.0022 (8)0.0033 (9)
C140.0379 (12)0.0310 (12)0.0253 (10)0.0017 (9)0.0073 (9)0.0011 (8)
C150.0255 (10)0.0350 (12)0.0340 (11)0.0006 (9)0.0078 (8)0.0019 (9)
C60.0405 (12)0.0244 (11)0.0277 (10)0.0041 (9)0.0041 (9)0.0028 (8)
C230.0340 (11)0.0253 (11)0.0385 (11)0.0075 (9)0.0100 (9)0.0030 (9)
C40.0369 (12)0.0279 (11)0.0454 (13)0.0010 (9)0.0015 (10)0.0159 (10)
C220.0401 (12)0.0222 (10)0.0384 (12)0.0037 (9)0.0122 (10)0.0033 (9)
C50.0504 (15)0.0548 (16)0.0350 (12)0.0052 (12)0.0069 (11)0.0127 (12)
C250.0425 (13)0.0381 (13)0.0423 (13)0.0001 (11)0.0034 (10)0.0091 (11)
C70.097 (2)0.0572 (18)0.0293 (13)0.0235 (17)0.0078 (14)0.0054 (12)
C240.0432 (14)0.0413 (15)0.0613 (16)0.0180 (11)0.0019 (12)0.0046 (13)
C170.0596 (17)0.0595 (18)0.0492 (15)0.0086 (14)0.0274 (13)0.0059 (13)
C80.113 (3)0.072 (2)0.0346 (14)0.033 (2)0.0104 (16)0.0004 (14)
Geometric parameters (Å, º) top
O2—C31.199 (2)C13—H130.9300
O3—C31.331 (2)C14—C151.388 (3)
O3—C41.460 (3)C15—H150.9300
O4—C61.201 (3)C23—C221.397 (3)
O5—C61.322 (3)C23—C241.496 (3)
O5—C71.465 (3)C4—C51.495 (3)
O1—C141.367 (3)C4—H4A0.9700
O1—C171.428 (3)C4—H4B0.9700
N1—C211.355 (3)C22—H220.9300
N1—N21.367 (2)C5—H5A0.9600
N1—C11.466 (2)C5—H5B0.9600
N2—C231.331 (3)C5—H5C0.9600
C1—C111.517 (3)C25—H25A0.9600
C1—C21.533 (3)C25—H25B0.9600
C1—H10.9800C25—H25C0.9600
C2—C31.521 (3)C7—C81.424 (4)
C2—C61.531 (3)C7—H7A0.9700
C2—H20.9800C7—H7B0.9700
C11—C121.390 (3)C24—H24A0.9600
C11—C161.391 (3)C24—H24B0.9600
C12—C131.376 (3)C24—H24C0.9600
C12—H120.9300C17—H17A0.9600
C21—C221.372 (3)C17—H17B0.9600
C21—C251.490 (3)C17—H17C0.9600
C16—C151.385 (3)C8—H8A0.9600
C16—H160.9300C8—H8B0.9600
C13—C141.393 (3)C8—H8C0.9600
C3—O3—C4116.03 (16)N2—C23—C24120.3 (2)
C6—O5—C7115.4 (2)C22—C23—C24128.4 (2)
C14—O1—C17117.87 (19)O3—C4—C5110.0 (2)
C21—N1—N2112.18 (17)O3—C4—H4A109.7
C21—N1—C1127.50 (16)C5—C4—H4A109.7
N2—N1—C1119.92 (16)O3—C4—H4B109.7
C23—N2—N1104.46 (17)C5—C4—H4B109.7
N1—C1—C11111.05 (15)H4A—C4—H4B108.2
N1—C1—C2108.18 (15)C21—C22—C23105.97 (19)
C11—C1—C2112.80 (16)C21—C22—H22127.0
N1—C1—H1108.2C23—C22—H22127.0
C11—C1—H1108.2C4—C5—H5A109.5
C2—C1—H1108.2C4—C5—H5B109.5
C3—C2—C6105.57 (15)H5A—C5—H5B109.5
C3—C2—C1110.98 (16)C4—C5—H5C109.5
C6—C2—C1110.86 (16)H5A—C5—H5C109.5
C3—C2—H2109.8H5B—C5—H5C109.5
C6—C2—H2109.8C21—C25—H25A109.5
C1—C2—H2109.8C21—C25—H25B109.5
C12—C11—C16118.10 (18)H25A—C25—H25B109.5
C12—C11—C1120.23 (17)C21—C25—H25C109.5
C16—C11—C1121.66 (17)H25A—C25—H25C109.5
O2—C3—O3125.32 (19)H25B—C25—H25C109.5
O2—C3—C2124.59 (18)C8—C7—O5108.6 (2)
O3—C3—C2110.01 (16)C8—C7—H7A110.0
C13—C12—C11121.13 (19)O5—C7—H7A110.0
C13—C12—H12119.4C8—C7—H7B110.0
C11—C12—H12119.4O5—C7—H7B110.0
N1—C21—C22106.12 (18)H7A—C7—H7B108.3
N1—C21—C25123.09 (19)C23—C24—H24A109.5
C22—C21—C25130.8 (2)C23—C24—H24B109.5
C15—C16—C11121.46 (19)H24A—C24—H24B109.5
C15—C16—H16119.3C23—C24—H24C109.5
C11—C16—H16119.3H24A—C24—H24C109.5
C12—C13—C14120.21 (19)H24B—C24—H24C109.5
C12—C13—H13119.9O1—C17—H17A109.5
C14—C13—H13119.9O1—C17—H17B109.5
O1—C14—C15124.7 (2)H17A—C17—H17B109.5
O1—C14—C13115.74 (19)O1—C17—H17C109.5
C15—C14—C13119.52 (19)H17A—C17—H17C109.5
C16—C15—C14119.56 (19)H17B—C17—H17C109.5
C16—C15—H15120.2C7—C8—H8A109.5
C14—C15—H15120.2C7—C8—H8B109.5
O4—C6—O5124.9 (2)H8A—C8—H8B109.5
O4—C6—C2124.10 (19)C7—C8—H8C109.5
O5—C6—C2110.92 (18)H8A—C8—H8C109.5
N2—C23—C22111.27 (19)H8B—C8—H8C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O2i0.932.513.358 (3)152
Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC20H26N2O5
Mr374.43
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)11.9618 (3), 7.9681 (2), 21.1269 (6)
β (°) 96.504 (1)
V3)2000.70 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.23 × 0.17 × 0.14
Data collection
DiffractometerBruker X8 APEXII CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
18616, 3921, 3177
Rint0.027
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.154, 1.05
No. of reflections3921
No. of parameters249
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.68, 0.45

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O2i0.932.513.358 (3)152
Symmetry code: (i) x+1, y, z+1.
 

Acknowledgements

This work was supported by grants from Project PGR-UMP-BH-2005, the Centre National de Recherche Scientifique, CNRS (France), the Centre National pour la Recherche Scientifique et Technique, CNRST (Morocco), and the CURI (Morocco).

References

First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDayam, R., Al-Mawsawi, L. Q. & Neamati, N. (2007). Bioorg. Med. Chem. Lett. 17, 6155–6159.  Web of Science CrossRef PubMed CAS
First citationPatil, S., Kamath, S., Sanchez, T., Neamati, N., Schinazi, R. F. & Buolamwini, J. K. (2007). Bioorg. Med. Chem. 15, 1212–1228.  Web of Science CrossRef PubMed CAS
First citationPommier, Y. & Neamati, N. (2006). Bioorg. Med. Chem. 14, 3785–3792.  Web of Science PubMed
First citationRamkumar, K., Tambov, K. V., Gundla, R., Manaev, A. V., Yarovenko, V., Traven, V. F. & Neamati, N. (2008). Bioorg. Med. Chem. 16, 8988–8998.  Web of Science CrossRef PubMed CAS
First citationSechi, M., Carta, F., Sannia, L., Dallocchio, R., Dessì, A., Al-Safi, R. I. & Neamati, N. (2009). Antiviral Res. 81, 267–276.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  Web of Science CrossRef CAS IUCr Journals
First citationZeng, L. F., Zhang, H.-S. W., ang, Y. H., Sanchez, T., Zheng, Y. T., Neamati, N. & Long, Y. Q. (2008). Bioorg. Med. Chem. Lett. 18, 4521–4524.  Web of Science CrossRef PubMed CAS

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds