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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 1| January 2015| Pages o56-o57
https://doi.org/10.1107/S2056989014027133

Crystal structure of N-(propan-2-yl­carbamo­thio­yl)benzamide

Jerry P. Jasinski,a Mehmet Akkurt,b Shaaban K. Mohamed,c,d Mohamed A. Gade and Mustafa R. Albayatif*

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 9 December 2014; accepted 11 December 2014; online 1 January 2015)

In the crystal structure of the title compound, C11H14N2OS, the six atoms of the central C2N2OS residue are coplanar (r.m.s. deviation = 0.002 Å), which facilitates the formation of an intra­molecular N—H⋯O hydrogen bond, which closes an S(6) loop. The terminal phenyl ring is inclined with respect to the central plane [dihedral angle = 42.10 (6)°]. The most prominent feature of the crystal packing is the formation of {⋯HNCS}2 synthons resulting in centrosymmetric dimers.

CCDC reference: 1038725

Similar articles

1. Related literature

For use of thio­ureas as building blocks in the synthesis of various organic compounds, see: Burgeson et al. (2012[Burgeson, J. R., Moore, A. L., Boutilier, J. K., Cerruti, N. R., Gharaibeh, D. N., Lovejoy, C. E., Amberg, S. M., Hruby, D. E., Tyavanagimatt, S. R., Allen, R. D. & Dai, D. (2012). Bioorg. Med. Chem. Lett. 22, 4263-4272.]); Vega-Pérez et al. (2012[Vega-Pérez, J. M., Periñán, I., Argandoña, M., Vega-Holm, M., Palo-Nieto, C., Burgos-Morón, E., López-Lázaro, M., Vargas, C., Nieto, J. J. & Iglesias-Guerra, F. (2012). Eur. J. Med. Chem. 58, 591-612.]); Yao et al. (2012[Yao, J., Chen, J., He, Z., Sun, W. & Xu, W. (2012). Bioorg. Med. Chem. 20, 2923-2929.]); Shantharam et al. (2013[Shantharam, C. S., Suyoga Vardhan, D. M., Suhas, R., Sridhara, M. B. & Gowda, D. C. (2013). Eur. J. Med. Chem. 60, 325-332.]); Yang et al. (2013[Yang, W., Hu, Y., Yang, Y. S., Zhang, F., Zhang, Y. B., Wang, X. L., Tang, J. F., Zhong, W. Q. & Zhu, H. L. (2013). Bioorg. Med. Chem. 21, 1050-1063.]). For use of thio­urea-containing compounds in medicinal applications, see: Rodriguez-Fernandez et al. (2005[Rodríguez-Fernández, E., Manzano, J. L., Benito, J. J., Hermosa, R., Monte, E. & Criado, J. J. (2005). J. Inorg. Biochem. 99, 1558-1572.]); Rauf et al. (2012[Rauf, M., Ebihara, M., Badshah, A. & Imtiaz-ud-Din (2012). Acta Cryst. E68, o119.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C11H14N2OS

  • Mr = 222.30

  • Monoclinic, P 21 /c

  • a = 11.2147 (4) Å

  • b = 5.3988 (2) Å

  • c = 19.6834 (7) Å

  • β = 102.031 (4)°

  • V = 1165.57 (7) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 2.27 mm−1

  • T = 293 K

  • 0.28 × 0.22 × 0.18 mm

2.2. Data collection

  • Agilent Xcalibur, Eos, Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.828, Tmax = 1.000

  • 3844 measured reflections

  • 2189 independent reflections

  • 1944 reflections with I > 2σ(I)

  • Rint = 0.025

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.146

  • S = 1.08

  • 2189 reflections

  • 146 parameters

  • 2 restraints

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

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯S1i 0.81 (2) 2.66 (2) 3.4439 (19) 165 (2)
N2—H2N⋯O1 0.87 (2) 2.00 (3) 2.662 (2) 132 (2)
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: CrysAlis PRO (Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2014 (Gruene et al., 2014[Gruene, T., Hahn, H. W., Luebben, A. V., Meilleur, F. & Sheldrick, G. M. (2014). J. Appl. Cryst. 47, 462-466.]); program(s) used to refine structure: SHELXL2014 (Gruene et al., 2014[Gruene, T., Hahn, H. W., Luebben, A. V., Meilleur, F. & Sheldrick, G. M. (2014). J. Appl. Cryst. 47, 462-466.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1038725

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989014027133/tk5351sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989014027133/tk5351Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989014027133/tk5351Isup3.cml

checkCIF report


Structural commentary top

Compounds containing thio­urea linkage are very useful building blocks for the synthesis of a wide range of multiheterocyclic and macromolecular compounds. Thio­ureas have proved to be useful substances in drug research in recent years (Burgeson et al., 2012; Vega-Pérez et al., 2012; Yao et al., 2012; Shantharam et al., 2013; Yang et al., 2013). Symmetrical and unsymmetrical thio­ureas have shown anti-fungal activity against the plant pathogens like Penicillium expansum and Fusarium oxysporum (Rodriguez-Fernandez et al., 2005). Also, 1,3-di­alkyl or di­aryl thio­ureas exhibited significant anti-fungal activity against Pyricularia oryzae and Drechslera oryzae (Rauf et al., 2012). In light of this, and following to our on-going study in synthesis of bio-active molecules, we report here the synthesis and crystal structure of the title compound.

In the structure of the title compound, Fig. 1, intra­molecular N—H···O and inter­molecular N—H···S inter­actions are noted (Table 1).

Synthesis and crystallization top

Freshly prepared benzoyl chloride 5 ml (0.043 mol) was added drop wise to a solution of 3.2 g (0.042 mol) of ammonium thio­cyanate in 20 ml dry acetone with stirring. The reaction mixture was refluxed for 3 h. The obtained solid precipitate ammonium chloride was filtered off. The formed benzoyl iso­thio­cyanate in the filtrate was added to a solution of 3.1 ml (0.0425 mol) of 2-amino-iso­propane in 20 ml dry acetone. The reaction mixture was heated under reflux for 5 h, then poured into a beaker containing some ice cubes. The resulting precipitate was collected by filtration, washed several times with cold ethanol/water and purified by recrystallization from ethanol/di­chloro­methane mixture (1:1). Yield (63%); colourless solid, m.p 418 K.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C). The hydrogen atoms attached to N1 and N2 were found from difference Fourier maps and were refined with the distance contratin N—H = 0.86±0.02 Å with unrestrained Uiso.

Related literature top

For use of thioureas as building blocks in the synthesis of various organic compounds, see: Burgeson et al. (2012); Vega-Pérez et al. (2012); Yao et al. (2012); Shantharam et al. (2013); Yang et al. (2013). For use of thiourea-containing compounds in medicinal applications, see: Rodriguez-Fernandez et al. (2005); Rauf et al. (2012).

Structure description top

Compounds containing thio­urea linkage are very useful building blocks for the synthesis of a wide range of multiheterocyclic and macromolecular compounds. Thio­ureas have proved to be useful substances in drug research in recent years (Burgeson et al., 2012; Vega-Pérez et al., 2012; Yao et al., 2012; Shantharam et al., 2013; Yang et al., 2013). Symmetrical and unsymmetrical thio­ureas have shown anti-fungal activity against the plant pathogens like Penicillium expansum and Fusarium oxysporum (Rodriguez-Fernandez et al., 2005). Also, 1,3-di­alkyl or di­aryl thio­ureas exhibited significant anti-fungal activity against Pyricularia oryzae and Drechslera oryzae (Rauf et al., 2012). In light of this, and following to our on-going study in synthesis of bio-active molecules, we report here the synthesis and crystal structure of the title compound.

In the structure of the title compound, Fig. 1, intra­molecular N—H···O and inter­molecular N—H···S inter­actions are noted (Table 1).

For use of thioureas as building blocks in the synthesis of various organic compounds, see: Burgeson et al. (2012); Vega-Pérez et al. (2012); Yao et al. (2012); Shantharam et al. (2013); Yang et al. (2013). For use of thiourea-containing compounds in medicinal applications, see: Rodriguez-Fernandez et al. (2005); Rauf et al. (2012).

Synthesis and crystallization top

Freshly prepared benzoyl chloride 5 ml (0.043 mol) was added drop wise to a solution of 3.2 g (0.042 mol) of ammonium thio­cyanate in 20 ml dry acetone with stirring. The reaction mixture was refluxed for 3 h. The obtained solid precipitate ammonium chloride was filtered off. The formed benzoyl iso­thio­cyanate in the filtrate was added to a solution of 3.1 ml (0.0425 mol) of 2-amino-iso­propane in 20 ml dry acetone. The reaction mixture was heated under reflux for 5 h, then poured into a beaker containing some ice cubes. The resulting precipitate was collected by filtration, washed several times with cold ethanol/water and purified by recrystallization from ethanol/di­chloro­methane mixture (1:1). Yield (63%); colourless solid, m.p 418 K.

Refinement details top

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C). The hydrogen atoms attached to N1 and N2 were found from difference Fourier maps and were refined with the distance contratin N—H = 0.86±0.02 Å with unrestrained Uiso.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2014 (Gruene et al., 2014); program(s) used to refine structure: SHELXL2014 (Gruene et al., 2014); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Perspective view of the title molecule with atom labeling scheme and 50% probability ellipsoids.
[Figure 2] Fig. 2. Packing viewed down the b axis showing stacks of pairs of molecules connected by N—H···S interactions.
N-(Propan-2-ylcarbamothioyl)benzamide top
Crystal data top
C11H14N2OSF(000) = 472
Mr = 222.30Dx = 1.267 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 1804 reflections
a = 11.2147 (4) Åθ = 4.0–71.4°
b = 5.3988 (2) ŵ = 2.27 mm−1
c = 19.6834 (7) ÅT = 293 K
β = 102.031 (4)°Prism, colourless
V = 1165.57 (7) Å30.28 × 0.22 × 0.18 mm
Z = 4
Data collection top
Agilent Xcalibur, Eos, Gemini
diffractometer		2189 independent reflections
Radiation source: Enhance (Cu) X-ray Source1944 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 16.0416 pixels mm-1θmax = 71.3°, θmin = 4.0°
ω scansh = −12→13
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)		k = −6→5
Tmin = 0.828, Tmax = 1.000l = −18→24
3844 measured reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.0871P)2 + 0.3862P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2189 reflectionsΔρmax = 0.37 e Å−3
146 parametersΔρmin = −0.34 e Å−3
Crystal data top
C11H14N2OSV = 1165.57 (7) Å3
Mr = 222.30Z = 4
Monoclinic, P21/cCu Kα radiation
a = 11.2147 (4) ŵ = 2.27 mm−1
b = 5.3988 (2) ÅT = 293 K
c = 19.6834 (7) Å0.28 × 0.22 × 0.18 mm
β = 102.031 (4)°
Data collection top
Agilent Xcalibur, Eos, Gemini
diffractometer		2189 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)		1944 reflections with I > 2σ(I)
Tmin = 0.828, Tmax = 1.000Rint = 0.025
3844 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0492 restraints
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.37 e Å−3
2189 reflectionsΔρmin = −0.34 e Å−3
146 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S10.60730 (5)0.80543 (14)0.08368 (3)0.0464 (2)
O10.86531 (13)1.0046 (3)−0.05679 (8)0.0392 (5)
N10.69070 (16)1.0345 (3)−0.01498 (9)0.0321 (5)
N20.82704 (16)0.7717 (3)0.05595 (9)0.0337 (5)
C10.63795 (19)1.4665 (4)−0.10695 (11)0.0334 (6)
C20.5930 (2)1.6272 (4)−0.16095 (12)0.0392 (6)
C30.6171 (2)1.5865 (4)−0.22650 (11)0.0414 (7)
C40.6865 (2)1.3853 (5)−0.23779 (11)0.0402 (7)
C50.73328 (19)1.2248 (4)−0.18386 (11)0.0342 (6)
C60.70827 (17)1.2641 (4)−0.11803 (10)0.0293 (5)
C70.76319 (18)1.0900 (4)−0.06135 (10)0.0310 (6)
C80.71668 (19)0.8697 (4)0.04084 (10)0.0322 (6)
C90.8684 (2)0.5923 (4)0.11200 (11)0.0389 (7)
C100.9666 (2)0.4305 (4)0.09293 (13)0.0452 (7)
C110.9154 (3)0.7308 (6)0.17988 (13)0.0592 (9)
H10.621201.49370−0.063200.0400*
H1N0.6216 (16)1.085 (4)−0.0236 (11)0.022 (5)*
H20.546401.76300−0.153400.0470*
H2N0.880 (2)0.814 (5)0.0317 (14)0.048 (8)*
H30.586601.69470−0.262700.0500*
H40.701901.35740−0.281800.0480*
H50.781201.09110−0.191400.0410*
H90.799500.487900.117300.0470*
H10A0.934000.342900.050700.0680*
H10B0.994700.313900.129600.0680*
H10C1.033600.532200.086400.0680*
H11A0.981800.836600.174800.0890*
H11B0.943200.613700.216500.0890*
H11C0.850900.829200.191100.0890*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0297 (3)0.0743 (5)0.0364 (3)0.0061 (2)0.0096 (2)0.0129 (3)
O10.0309 (8)0.0465 (9)0.0415 (8)0.0072 (6)0.0106 (6)0.0113 (7)
N10.0278 (8)0.0390 (9)0.0293 (8)0.0046 (7)0.0056 (6)0.0054 (7)
N20.0306 (9)0.0383 (10)0.0314 (9)0.0010 (7)0.0046 (7)0.0076 (7)
C10.0350 (10)0.0309 (10)0.0331 (10)−0.0033 (8)0.0041 (8)−0.0023 (8)
C20.0400 (11)0.0299 (10)0.0448 (12)−0.0012 (9)0.0019 (9)0.0025 (9)
C30.0418 (12)0.0405 (12)0.0377 (11)−0.0059 (9)−0.0014 (9)0.0124 (9)
C40.0369 (11)0.0544 (14)0.0291 (10)−0.0081 (10)0.0064 (8)0.0062 (9)
C50.0284 (10)0.0408 (11)0.0341 (10)−0.0027 (8)0.0080 (8)0.0032 (8)
C60.0260 (9)0.0304 (9)0.0300 (9)−0.0055 (7)0.0022 (7)0.0023 (8)
C70.0321 (10)0.0314 (10)0.0286 (9)−0.0038 (8)0.0043 (7)−0.0007 (8)
C80.0336 (10)0.0363 (10)0.0255 (9)−0.0020 (8)0.0033 (7)−0.0004 (8)
C90.0367 (11)0.0412 (12)0.0379 (11)0.0022 (9)0.0059 (9)0.0114 (9)
C100.0487 (13)0.0347 (11)0.0506 (13)0.0075 (10)0.0065 (10)0.0043 (10)
C110.0607 (16)0.079 (2)0.0334 (12)0.0280 (14)−0.0003 (11)0.0010 (12)
Geometric parameters (Å, º) top
S1—C81.664 (2)C9—C111.526 (3)
O1—C71.220 (3)C9—C101.513 (3)
N1—C71.376 (3)C1—H10.9300
N1—C81.397 (3)C2—H20.9300
N2—C81.322 (3)C3—H30.9300
N2—C91.469 (3)C4—H40.9300
C1—C21.383 (3)C5—H50.9300
C1—C61.391 (3)C9—H90.9800
N1—H1N0.806 (19)C10—H10A0.9600
N2—H2N0.87 (2)C10—H10B0.9600
C2—C31.390 (3)C10—H10C0.9600
C3—C41.381 (3)C11—H11A0.9600
C4—C51.386 (3)C11—H11B0.9600
C5—C61.398 (3)C11—H11C0.9600
C6—C71.490 (3)
C7—N1—C8127.26 (18)C6—C1—H1120.00
C8—N2—C9124.57 (18)C1—C2—H2120.00
C2—C1—C6120.0 (2)C3—C2—H2120.00
C7—N1—H1N117.5 (15)C2—C3—H3120.00
C8—N1—H1N114.5 (15)C4—C3—H3120.00
C1—C2—C3120.3 (2)C3—C4—H4120.00
C8—N2—H2N119.2 (17)C5—C4—H4120.00
C9—N2—H2N116.2 (17)C4—C5—H5120.00
C2—C3—C4119.9 (2)C6—C5—H5120.00
C3—C4—C5120.3 (2)N2—C9—H9109.00
C4—C5—C6119.9 (2)C10—C9—H9109.00
C1—C6—C7122.51 (18)C11—C9—H9109.00
C5—C6—C7117.82 (18)C9—C10—H10A109.00
C1—C6—C5119.63 (19)C9—C10—H10B110.00
O1—C7—N1122.96 (19)C9—C10—H10C109.00
O1—C7—C6121.90 (18)H10A—C10—H10B110.00
N1—C7—C6115.14 (17)H10A—C10—H10C109.00
S1—C8—N1118.47 (16)H10B—C10—H10C109.00
S1—C8—N2123.87 (16)C9—C11—H11A110.00
N1—C8—N2117.65 (19)C9—C11—H11B109.00
N2—C9—C11109.39 (19)C9—C11—H11C109.00
C10—C9—C11111.3 (2)H11A—C11—H11B109.00
N2—C9—C10109.06 (18)H11A—C11—H11C109.00
C2—C1—H1120.00H11B—C11—H11C110.00
C7—N1—C8—N27.1 (3)C2—C1—C6—C7177.6 (2)
C7—N1—C8—S1−172.18 (17)C1—C2—C3—C4−0.2 (3)
C8—N1—C7—O1−3.3 (3)C2—C3—C4—C5−0.6 (3)
C8—N1—C7—C6176.95 (19)C3—C4—C5—C61.2 (3)
C9—N2—C8—S10.4 (3)C4—C5—C6—C7−178.5 (2)
C9—N2—C8—N1−178.83 (18)C4—C5—C6—C1−0.9 (3)
C8—N2—C9—C10151.8 (2)C1—C6—C7—O1−140.9 (2)
C8—N2—C9—C11−86.2 (3)C5—C6—C7—O136.7 (3)
C6—C1—C2—C30.4 (3)C5—C6—C7—N1−143.55 (19)
C2—C1—C6—C50.1 (3)C1—C6—C7—N138.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···S1i0.81 (2)2.66 (2)3.4439 (19)165 (2)
N2—H2N···O10.87 (2)2.00 (3)2.662 (2)132 (2)
Symmetry code: (i) −x+1, −y+2, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···S1i0.806 (19)2.659 (19)3.4439 (19)165 (2)
N2—H2N···O10.87 (2)2.00 (3)2.662 (2)132 (2)
Symmetry code: (i) −x+1, −y+2, −z.
 

Acknowledgements

JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer. SKM would like to thank Keene State College for providing the X-ray data and Manchester Metropolitan University for supporting this study.

References

First citationAgilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.  Google Scholar
 First citationBurgeson, J. R., Moore, A. L., Boutilier, J. K., Cerruti, N. R., Gharaibeh, D. N., Lovejoy, C. E., Amberg, S. M., Hruby, D. E., Tyavanagimatt, S. R., Allen, R. D. & Dai, D. (2012). Bioorg. Med. Chem. Lett. 22, 4263–4272.  CrossRef CAS PubMed Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationGruene, T., Hahn, H. W., Luebben, A. V., Meilleur, F. & Sheldrick, G. M. (2014). J. Appl. Cryst. 47, 462–466.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationRauf, M., Ebihara, M., Badshah, A. & Imtiaz-ud-Din (2012). Acta Cryst. E68, o119.  CrossRef IUCr Journals Google Scholar
 First citationRodríguez-Fernández, E., Manzano, J. L., Benito, J. J., Hermosa, R., Monte, E. & Criado, J. J. (2005). J. Inorg. Biochem. 99, 1558–1572.  Web of Science PubMed Google Scholar
 First citationShantharam, C. S., Suyoga Vardhan, D. M., Suhas, R., Sridhara, M. B. & Gowda, D. C. (2013). Eur. J. Med. Chem. 60, 325–332.  CrossRef CAS PubMed Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationVega-Pérez, J. M., Periñán, I., Argandoña, M., Vega-Holm, M., Palo-Nieto, C., Burgos-Morón, E., López-Lázaro, M., Vargas, C., Nieto, J. J. & Iglesias-Guerra, F. (2012). Eur. J. Med. Chem. 58, 591–612.  PubMed Google Scholar
 First citationYang, W., Hu, Y., Yang, Y. S., Zhang, F., Zhang, Y. B., Wang, X. L., Tang, J. F., Zhong, W. Q. & Zhu, H. L. (2013). Bioorg. Med. Chem. 21, 1050–1063.  CrossRef CAS PubMed Google Scholar
 First citationYao, J., Chen, J., He, Z., Sun, W. & Xu, W. (2012). Bioorg. Med. Chem. 20, 2923–2929.  CrossRef CAS PubMed Google Scholar

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ISSN: 2056-9890
Volume 71| Part 1| January 2015| Pages o56-o57
https://doi.org/10.1107/S2056989014027133
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