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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-3-(3,4-Di­fluoro­phen­yl)-1-(3,4-di­meth­­oxy­phen­yl)prop-2-en-1-one

aSchool of Pharmaceutical Sciences, Wenzhou Medical College, Wenzhou 325035, People's Republic of China
*Correspondence e-mail: lzgcnu@163.com

(Received 9 April 2013; accepted 18 May 2013; online 25 May 2013)

In the title compound, C17H14F2O3, the dihedral angle between the benzene rings is 20.56 (8)° and the H atoms at the central propenone group are trans configured. One of the F atoms is disordered over two positions (occupancy ratio 0.57:0.43) and was refined using a split model. In the crystal, the molecules are linked into centrosymmetrical dimers and are further connected into a three-dimensional network via weak C—H⋯O interactions.

Related literature

For related structures, see: Peng et al.(2010[Peng, J., Xu, H., Li, Z., Zhang, Y. & Wu, J. (2010). Acta Cryst. E66, o1156-o1157.]); Wu et al. (2010[Wu, X., Cai, X., Zheng, X., Zhang, Z. & Ye, X. (2010). Acta Cryst. E66, o3015.], 2011[Wu, J. Z., Li, J. L., Cai, Y. P., Pan, Y., Ye, F. Q., Zhang, Y. L., Zhao, Y. J., Yang, S. L., Li, X. K. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.], 2012b[Wu, J. Z., Jiang, X., Zhao, C. G., Li, X. K. & Yang, S. L. (2012b). Z. Kristallogr. New Cryst. Struct. 227, 215-216.]). For background to and applications of chalcones, see: Boumendjel et al. (2008[Boumendjel, A., Boccard, J., Carrupt, P. A., Nicolle, E., Blanc, M., Geze, A., Choisnard, L., Wouessidjewe, D., Matera, E. L. & Dumontet, C. (2008). J. Med. Chem. 51, 2307-2310.]); Kumar et al. (2011[Kumar, V., Kumar, S., Hassan, M., Wu, H., Thimmulappa, R. K., Kumar, A., Sharma, S. K., Parmar, V. S., Biswal, S. & Malhotra, S. V. (2011). J. Med. Chem. 54, 4147-4159.]); Wu et al. (2011[Wu, J. Z., Li, J. L., Cai, Y. P., Pan, Y., Ye, F. Q., Zhang, Y. L., Zhao, Y. J., Yang, S. L., Li, X. K. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.], 2012a[Wu, J. Z., Wang, C., Cai, Y. P., Peng, J., Liang, D. L., Zhao, Y. J., Yang, S. L., Li, X. K., Wu, X. P. & Liang, G. (2012a). Med. Chem. Res. 21, 444-452.]); Zhang et al. (2011[Zhang, H. J., Qian, Y., Zhu, D. D., Yang, X. G. & Zhu, H. L. (2011). Eur. J. Med. Chem. 46, 4702-4708.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14F2O3

  • Mr = 304.28

  • Monoclinic, P 21 /n

  • a = 8.7444 (9) Å

  • b = 8.4832 (9) Å

  • c = 19.829 (2) Å

  • β = 94.053 (2)°

  • V = 1467.2 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 293 K

  • 0.21 × 0.15 × 0.11 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.977, Tmax = 0.988

  • 8592 measured reflections

  • 2876 independent reflections

  • 2121 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.129

  • S = 1.04

  • 2876 reflections

  • 201 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1⋯O1i 0.93 2.44 3.321 (2) 159
C5—H5⋯O2ii 0.93 2.60 3.2769 (15) 130
C5—H5⋯O3ii 0.93 2.49 3.3950 (15) 164
Symmetry codes: (i) -x+1, -y+1, -z; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound is a biologically active derivative of chalcone. Chalcones constitute an important group of natural products and some of them possess a wide range of biological activities including anti-inflammatory and anti-tumor (Boumendjel et al., 2008; Kumar et al., 2011; Zhang et al., 2011). As part of our ongoing studies on chalcones (Wu et al., 2012a,b; 2011), the title compound was synthesized and its crystal structure is reported here.

In the crystal structure, the dihedral angle between the mean planes of the difluorophenyl and the dimethoxyphenyl rings amount to 20.56 (8)°. The H atoms of the central propenone group are trans configurated. The two methoxy groups attached to C13 and C14 are almost coplanar with the benzene ring.

Related literature top

For related structures, see: Peng et al.(2010); Wu et al. (2010, 2011, 2012b). For background to and applications of chalcones, see: Boumendjel et al. (2008); Kumar et al. (2011); Wu et al. (2011, 2012a); Zhang et al. (2011).

Experimental top

1-(3,4-difluorophenyl) ethanone (0.01 mol) and 2,3-dimethoxybenzaldehyde (0.01 mol) were dissolved in methanol (50 ml). Sodium hydroxide (5 ml, 20%) was added drop wised to the solution, which was stirred at ambient temperature. The content of the flask were poured into ice-cold water, and the resulting crude solid was collected by filtration. The compound was purified by flash column and single crystals were obtained by slow evaporation from an ethanol/ dichloromethane solution (1:2, v/v) at 293 K.

Refinement top

The hydrogen atoms were positioned with idalized geometry and refined isotropic with Uiso(H) = 1.2 Ueq(C) (1.5 for methyl H atoms) using a riding model. One of the fluorine atoms was disordered over two positions and was refined using a split model with sof = 0.55 and 0.45.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Sheldrick, 2008); 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. Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level. Disordering is shown as full and open bonds.
(E)-3-(3,4-Difluorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one top
Crystal data top
C17H14F2O3F(000) = 632
Mr = 304.28Dx = 1.377 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.7444 (9) ÅCell parameters from 2015 reflections
b = 8.4832 (9) Åθ = 5.0–54.2°
c = 19.829 (2) ŵ = 0.11 mm1
β = 94.053 (2)°T = 293 K
V = 1467.2 (3) Å3Prismatic, colorless
Z = 40.21 × 0.15 × 0.11 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2876 independent reflections
Radiation source: fine-focus sealed tube2121 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
phi and ω scansθmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1010
Tmin = 0.977, Tmax = 0.988k = 1010
8592 measured reflectionsl = 2420
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0703P)2 + 0.091P]
where P = (Fo2 + 2Fc2)/3
2876 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C17H14F2O3V = 1467.2 (3) Å3
Mr = 304.28Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.7444 (9) ŵ = 0.11 mm1
b = 8.4832 (9) ÅT = 293 K
c = 19.829 (2) Å0.21 × 0.15 × 0.11 mm
β = 94.053 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2876 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
2121 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.988Rint = 0.028
8592 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 1.04Δρmax = 0.19 e Å3
2876 reflectionsΔρmin = 0.15 e Å3
201 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)
F10.0102 (2)0.0304 (3)0.14625 (12)0.0862 (7)0.57
F1'0.1205 (3)0.2840 (4)0.03983 (14)0.0844 (9)0.43
F20.21164 (11)0.07757 (14)0.05038 (6)0.0743 (4)
O10.67825 (13)0.44604 (16)0.07214 (6)0.0643 (4)
O21.05520 (12)0.37085 (16)0.35153 (5)0.0569 (3)
O31.13490 (13)0.49922 (18)0.24315 (6)0.0711 (4)
C10.12377 (18)0.3023 (2)0.01589 (8)0.0512 (4)
H10.15360.37720.01480.061*
C20.02383 (9)0.24437 (11)0.01024 (4)0.0546 (4)
H20.09550.28090.02530.065*0.57
C30.06758 (9)0.13470 (11)0.05544 (4)0.0520 (4)
C40.03440 (9)0.08176 (11)0.10642 (4)0.0557 (4)
H4'0.00240.00470.13790.067*0.43
C50.18143 (9)0.13853 (11)0.11244 (4)0.0520 (4)
H50.24980.10230.14710.062*
C60.22850 (16)0.24987 (19)0.06709 (8)0.0431 (4)
C70.38359 (17)0.3175 (2)0.07232 (8)0.0457 (4)
H70.40640.38890.03890.055*
C80.49391 (17)0.2877 (2)0.11943 (8)0.0505 (4)
H80.47690.21390.15280.061*
C90.64366 (17)0.3684 (2)0.12068 (8)0.0474 (4)
C100.74973 (16)0.35850 (19)0.18235 (8)0.0441 (4)
C110.71003 (19)0.2904 (2)0.24136 (9)0.0588 (5)
H110.61450.24290.24260.071*
C120.80881 (19)0.2909 (2)0.29899 (9)0.0587 (5)
H120.77920.24390.33840.070*
C130.95050 (17)0.36056 (19)0.29820 (8)0.0459 (4)
C140.99356 (16)0.42987 (19)0.23785 (8)0.0458 (4)
C150.89489 (17)0.42856 (18)0.18126 (8)0.0449 (4)
H150.92420.47460.14160.054*
C161.0133 (2)0.3151 (3)0.41527 (9)0.0700 (6)
H16A0.91960.36480.42630.105*
H16B1.09310.33990.44940.105*
H16C0.99900.20300.41320.105*
C171.1804 (2)0.5882 (3)0.18825 (10)0.0762 (6)
H17A1.18380.52140.14930.114*
H17B1.28020.63200.19930.114*
H17C1.10830.67190.17860.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0593 (11)0.0901 (16)0.1083 (16)0.0182 (10)0.0008 (10)0.0475 (13)
F1'0.0602 (14)0.111 (2)0.0770 (17)0.0076 (14)0.0306 (13)0.0194 (16)
F20.0443 (5)0.0795 (8)0.0971 (9)0.0160 (5)0.0097 (5)0.0008 (6)
O10.0498 (7)0.0841 (10)0.0580 (7)0.0110 (6)0.0045 (6)0.0218 (7)
O20.0488 (6)0.0697 (8)0.0502 (7)0.0076 (6)0.0095 (5)0.0012 (6)
O30.0497 (7)0.1028 (11)0.0602 (8)0.0332 (7)0.0014 (6)0.0012 (7)
C10.0492 (9)0.0576 (11)0.0454 (9)0.0017 (8)0.0057 (7)0.0055 (8)
C20.0453 (9)0.0650 (12)0.0510 (10)0.0007 (8)0.0140 (8)0.0014 (8)
C30.0369 (8)0.0538 (10)0.0644 (10)0.0046 (7)0.0044 (7)0.0089 (8)
C40.0490 (9)0.0506 (11)0.0668 (11)0.0037 (8)0.0002 (8)0.0092 (8)
C50.0431 (9)0.0564 (11)0.0550 (10)0.0024 (8)0.0076 (7)0.0088 (8)
C60.0403 (8)0.0445 (9)0.0436 (8)0.0022 (7)0.0032 (6)0.0026 (7)
C70.0432 (8)0.0498 (10)0.0438 (9)0.0001 (7)0.0007 (7)0.0001 (7)
C80.0420 (8)0.0550 (10)0.0534 (10)0.0056 (7)0.0052 (7)0.0080 (8)
C90.0404 (8)0.0498 (10)0.0514 (9)0.0002 (7)0.0006 (7)0.0047 (8)
C100.0381 (8)0.0437 (9)0.0498 (9)0.0031 (7)0.0014 (7)0.0007 (7)
C110.0442 (9)0.0694 (12)0.0616 (11)0.0195 (8)0.0055 (8)0.0140 (9)
C120.0544 (10)0.0688 (12)0.0515 (10)0.0157 (9)0.0053 (8)0.0157 (8)
C130.0422 (8)0.0449 (9)0.0496 (9)0.0010 (7)0.0050 (7)0.0035 (7)
C140.0364 (8)0.0472 (10)0.0533 (9)0.0065 (7)0.0005 (7)0.0070 (7)
C150.0430 (8)0.0454 (9)0.0465 (9)0.0033 (7)0.0041 (7)0.0017 (7)
C160.0654 (11)0.0901 (15)0.0523 (11)0.0033 (10)0.0120 (9)0.0085 (10)
C170.0639 (12)0.0933 (16)0.0735 (13)0.0337 (11)0.0201 (10)0.0104 (11)
Geometric parameters (Å, º) top
F1—C41.313 (2)C7—H70.9300
F1'—C21.302 (2)C8—C91.476 (2)
F2—C31.3468 (12)C8—H80.9300
O1—C91.2220 (19)C9—C101.484 (2)
O2—C131.3516 (17)C10—C111.371 (2)
O2—C161.421 (2)C10—C151.403 (2)
O3—C141.3662 (18)C11—C121.383 (2)
O3—C171.405 (2)C11—H110.9300
C1—C21.3784 (18)C12—C131.374 (2)
C1—C61.391 (2)C12—H120.9300
C1—H10.9300C13—C141.408 (2)
C2—C31.3650C14—C151.366 (2)
C2—H20.9600C15—H150.9300
C3—C41.3753C16—H16A0.9600
C4—C51.3703C16—H16B0.9600
C4—H4'0.9600C16—H16C0.9600
C5—C61.3866 (18)C17—H17A0.9600
C5—H50.9300C17—H17B0.9600
C6—C71.469 (2)C17—H17C0.9600
C7—C81.319 (2)
C13—O2—C16118.12 (13)C8—C9—C10119.32 (14)
C14—O3—C17118.42 (14)C11—C10—C15118.39 (14)
C2—C1—C6120.61 (15)C11—C10—C9123.07 (14)
C2—C1—H1119.7C15—C10—C9118.47 (14)
C6—C1—H1119.7C10—C11—C12121.53 (15)
F1'—C2—C3118.67 (13)C10—C11—H11119.2
F1'—C2—C1121.57 (16)C12—C11—H11119.2
C3—C2—C1119.62 (8)C13—C12—C11120.20 (16)
C3—C2—H2120.2C13—C12—H12119.9
C1—C2—H2120.2C11—C12—H12119.9
F2—C3—C2120.03 (6)O2—C13—C12125.48 (15)
F2—C3—C4119.45 (6)O2—C13—C14115.52 (13)
C2—C3—C4120.5C12—C13—C14118.99 (14)
F1—C4—C5121.27 (9)O3—C14—C15125.60 (15)
F1—C4—C3118.29 (9)O3—C14—C13114.15 (13)
C5—C4—C3120.3C15—C14—C13120.22 (13)
C5—C4—H4'119.8C14—C15—C10120.68 (15)
C3—C4—H4'119.8C14—C15—H15119.7
C4—C5—C6120.17 (6)C10—C15—H15119.7
C4—C5—H5119.9O2—C16—H16A109.5
C6—C5—H5119.9O2—C16—H16B109.5
C5—C6—C1118.75 (13)H16A—C16—H16B109.5
C5—C6—C7122.34 (12)O2—C16—H16C109.5
C1—C6—C7118.89 (14)H16A—C16—H16C109.5
C8—C7—C6126.89 (15)H16B—C16—H16C109.5
C8—C7—H7116.6O3—C17—H17A109.5
C6—C7—H7116.6O3—C17—H17B109.5
C7—C8—C9121.78 (15)H17A—C17—H17B109.5
C7—C8—H8119.1O3—C17—H17C109.5
C9—C8—H8119.1H17A—C17—H17C109.5
O1—C9—C8120.35 (14)H17B—C17—H17C109.5
O1—C9—C10120.29 (14)
C6—C1—C2—F1'175.4 (2)O1—C9—C10—C11171.47 (18)
C6—C1—C2—C30.14 (19)C8—C9—C10—C116.5 (3)
F1'—C2—C3—F24.45 (17)O1—C9—C10—C155.4 (2)
C1—C2—C3—F2179.90 (13)C8—C9—C10—C15176.53 (15)
F1'—C2—C3—C4175.63 (17)C15—C10—C11—C120.5 (3)
C1—C2—C3—C40.03 (9)C9—C10—C11—C12176.42 (17)
F2—C3—C4—F13.98 (15)C10—C11—C12—C130.0 (3)
C2—C3—C4—F1176.10 (14)C16—O2—C13—C124.5 (3)
F2—C3—C4—C5179.96 (7)C16—O2—C13—C14174.74 (16)
C2—C3—C4—C50.0C11—C12—C13—O2178.70 (16)
F1—C4—C5—C6175.92 (18)C11—C12—C13—C140.5 (3)
C3—C4—C5—C60.02 (8)C17—O3—C14—C155.4 (3)
C4—C5—C6—C10.13 (17)C17—O3—C14—C13172.30 (16)
C4—C5—C6—C7178.41 (10)O2—C13—C14—O30.9 (2)
C2—C1—C6—C50.2 (2)C12—C13—C14—O3178.39 (16)
C2—C1—C6—C7178.53 (13)O2—C13—C14—C15178.80 (14)
C5—C6—C7—C82.0 (3)C12—C13—C14—C150.5 (2)
C1—C6—C7—C8176.24 (16)O3—C14—C15—C10177.60 (16)
C6—C7—C8—C9177.52 (15)C13—C14—C15—C100.0 (2)
C7—C8—C9—O111.8 (3)C11—C10—C15—C140.5 (2)
C7—C8—C9—C10166.18 (16)C9—C10—C15—C14176.55 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.932.443.321 (2)159
C5—H5···O2ii0.932.603.2769 (15)130
C5—H5···O3ii0.932.493.3950 (15)164
Symmetry codes: (i) x+1, y+1, z; (ii) x+3/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H14F2O3
Mr304.28
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)8.7444 (9), 8.4832 (9), 19.829 (2)
β (°) 94.053 (2)
V3)1467.2 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.21 × 0.15 × 0.11
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.977, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
8592, 2876, 2121
Rint0.028
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.129, 1.04
No. of reflections2876
No. of parameters201
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.15

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.932.443.321 (2)159
C5—H5···O2ii0.932.603.2769 (15)130
C5—H5···O3ii0.932.493.3950 (15)164
Symmetry codes: (i) x+1, y+1, z; (ii) x+3/2, y1/2, z+1/2.
 

Acknowledgements

This work was supported by Xinmiao Talent Project of Zhejiang Province (ZHP). The X-ray crystallographic facility at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, is gratefully acknowledged.

References

First citationBoumendjel, A., Boccard, J., Carrupt, P. A., Nicolle, E., Blanc, M., Geze, A., Choisnard, L., Wouessidjewe, D., Matera, E. L. & Dumontet, C. (2008). J. Med. Chem. 51, 2307–2310.  Web of Science CrossRef PubMed CAS
First citationBruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationKumar, V., Kumar, S., Hassan, M., Wu, H., Thimmulappa, R. K., Kumar, A., Sharma, S. K., Parmar, V. S., Biswal, S. & Malhotra, S. V. (2011). J. Med. Chem. 54, 4147–4159.  Web of Science CrossRef CAS PubMed
First citationPeng, J., Xu, H., Li, Z., Zhang, Y. & Wu, J. (2010). Acta Cryst. E66, o1156–o1157.  Web of Science CSD CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWu, X., Cai, X., Zheng, X., Zhang, Z. & Ye, X. (2010). Acta Cryst. E66, o3015.  Web of Science CSD CrossRef IUCr Journals
First citationWu, J. Z., Jiang, X., Zhao, C. G., Li, X. K. & Yang, S. L. (2012b). Z. Kristallogr. New Cryst. Struct. 227, 215–216.  CAS
First citationWu, J. Z., Li, J. L., Cai, Y. P., Pan, Y., Ye, F. Q., Zhang, Y. L., Zhao, Y. J., Yang, S. L., Li, X. K. & Liang, G. (2011). J. Med. Chem. 54, 8110–8123.  Web of Science CrossRef CAS PubMed
First citationWu, J. Z., Wang, C., Cai, Y. P., Peng, J., Liang, D. L., Zhao, Y. J., Yang, S. L., Li, X. K., Wu, X. P. & Liang, G. (2012a). Med. Chem. Res. 21, 444–452.  Web of Science CSD CrossRef CAS
First citationZhang, H. J., Qian, Y., Zhu, D. D., Yang, X. G. & Zhu, H. L. (2011). Eur. J. Med. Chem. 46, 4702–4708.  Web of Science CSD CrossRef CAS PubMed

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