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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N′-[(E)-(Furan-2-yl)methyl­­idene]-2-[4-(2-methyl­prop­yl)phen­yl]propano­hydrazide

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq, and fDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt
*Correspondence e-mail: shaabankamel@yahoo.com

(Received 19 February 2014; accepted 20 February 2014; online 26 February 2014)

In the title mol­ecule, C18H22N2O2, the furan and benzene rings form a dihedral angle of 70.17 (14)°. In the crystal, strong N—H⋯O and weak C—H⋯O hydrogen bonds link the mol­ecules into chains running parallel to [010].

Related literature

For the synthesis of compounds of similar structure to Ibuprofen undertaken as part of our ongoing study incorporating non-steroidal anti-inflammatory drugs (NSAIDs) as a substructure in the synthesis of potential bio-active pharmacophors, see: Mohamed et al. (2012[Mohamed, S. K., Albayati, M. R., Omara, W. A. M., Abdelhamid, A. A., Potgeiter, H., Hameed, A. S. & Al-Janabi, K. M. (2012). J. Chem. Pharm. Res. 4, 3505-3517.], 2013[Mohamed, S. K., Albayati, M. R., Younes, S. H. H. & Abed-Alkareem, M. G. (2013). CSJ, CSJ-97.]). For general harmful side-effects of NSAIDs, see: Neeraj et al. (2010[Neeraj, A., Chandrasekar, M. J. N., Sara, U. V. S. & Rohini, A. (2010). Int. J. Drug Deliv. Technol. 2, 12-17.]); Agrawal et al. (2010[Agrawal, N., Chandrasekar, M. J. N., Sara, U. V. S. & Rohini, A. (2010). Int. J. Drug Deliv. Technol. 2, 12-17.]); Champion et al. (1997[Champion, G. D., Feng, P. H., Azuma, T., Caughey, D. E., Chan, K. H., Kashiwazaki, S., Liu, H.-C., Nasution, A. R., Hobunaga, M., Prichanond, S., Torralba, T. P., Udom, V. & Yoo, M. C. (1997). Drugs, 53, 61-69.]); Asif (2009[Asif, H. (2009). Acta Pol. Pharm. Drug Res. 66, 513-521.]). For reduction of these side-effects, see: Parmeshwari et al. (2009[Parmeshwari, K. H., Murumkar, P. R., Giridhar, R. & Yadav, M. R. (2009). Mini Rev. Med. Chem. 9, 124-139.]); Alert (1958[Alert, A. (1958). Nature, 182, 421-423.]); Bundgaard (1991[Bundgaard, H. (1991). Drugs Future, 16, 443-458.]).

[Scheme 1]

Experimental

Crystal data
  • C18H22N2O2

  • Mr = 298.38

  • Orthorhombic, P b c a

  • a = 11.714 (3) Å

  • b = 8.430 (2) Å

  • c = 33.872 (8) Å

  • V = 3344.8 (14) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 150 K

  • 0.19 × 0.17 × 0.08 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.52, Tmax = 0.99

  • 55300 measured reflections

  • 4178 independent reflections

  • 2562 reflections with I > 2σ(I)

  • Rint = 0.154

Refinement
  • R[F2 > 2σ(F2)] = 0.077

  • wR(F2) = 0.248

  • S = 1.01

  • 4178 reflections

  • 203 parameters

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

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2N⋯O2i 0.96 (3) 1.86 (2) 2.791 (2) 164 (2)
C5—H5⋯O2i 0.95 2.49 3.296 (3) 142
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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


Comment top

Ibuprofen, as other common anti-inflammatory drugs (NSAIDs) which are widely employed in the treatment of pain and inflammation, has been reported to be associated with a number of undesirable effects which, in particular, include gastrointestinal (GI) toxicity (Neeraj et al., 2010; Agrawal et al., 2010; Champion et al., 1997). These studies confirmed that gastrointestinal side-effects of Iburofen and other aroylpropanoic acids are due to the presence of a free carboxylic group in the parent drug (Asif, 2009). Therefore, temporary masking or manipulation of the acidic group in NSAID's are promising means to reduce or to abolish the GI toxicity due to the local action mechanism (Parmeshwari et al., 2009; Alert 1958; Bundgaard, 1991). In view of such facts and following to our ongoing study incorporating NSAID's as a substructure in the synthesis of potential bio-active pharmacophors (Mohamed et al., 2012, 2013) we report the crystal structure of the title compound (I).

Fig. 1 shows the title molecule (I). The dihedral angle between the mean planes of the furan ring (O1/C1–C4) and the benzene ring (C9–C14) is 70.17 (14)°. The C5–N1–N2–C6, N2–N1–C5–C4, N1–N2–C6–C7 and N1–N2–C6–O2 torsion angles are -170.46 (19), -176.99 (19), 178.89 (17) and -0.3 (3)°, respectively. The bond lengths and bond angles in (I) are normal.

The crystal packing (Fig. 2) is directed by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) connecting the molecules into chains running parallel to the b axis.

Related literature top

For the synthesis of compounds of similar structure to Ibuprofen undertaken as part of our ongoing study incorporating non-steroidal anti-inflammatory drugs (NSAIDs) as a substructure in the synthesis of potential bio-active pharmacophors, see: Mohamed et al. (2012, 2013). For general harmful side-effects of NSAIDs, see: Neeraj et al. (2010); Agrawal et al. (2010); Champion et al. (1997); Asif (2009). For reduction of these side-effects, see: Parmeshwari et al. (2009); Alert (1958); Bundgaard (1991).

Experimental top

The title compound was prepared according to our reported method (Mohamed et al., 2012). Clear orange crystals suitable for X-ray analysis were grown from an ethanol solution of (I). M.p. 426–428 K.

Refinement top

The H atoms of N2 was located from a difference Fourier map and refined freely. The other H atoms were placed in geometrically idealized positions and refined using a riding model approximation with Uiso(H) = 1.2 or 1.5Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
[Figure 2] Fig. 2. View of the hydrogen bonding and packing of the title compound down the a axis.
N'-[(E)-(Furan-2-yl)methylidene]-2-[4-(2-methylpropyl)phenyl]propanohydrazide top
Crystal data top
C18H22N2O2F(000) = 1280
Mr = 298.38Dx = 1.185 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9972 reflections
a = 11.714 (3) Åθ = 2.4–28.2°
b = 8.430 (2) ŵ = 0.08 mm1
c = 33.872 (8) ÅT = 150 K
V = 3344.8 (14) Å3Slab, clear orange
Z = 80.19 × 0.17 × 0.08 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
4178 independent reflections
Radiation source: fine-focus sealed tube2562 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.154
Detector resolution: 8.3660 pixels mm-1θmax = 28.4°, θmin = 2.1°
φ and ω scansh = 1515
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 1111
Tmin = 0.52, Tmax = 0.99l = 4545
55300 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.077H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.248 w = 1/[σ2(Fo2) + (0.1555P)2 + 0.1359P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
4178 reflectionsΔρmax = 0.37 e Å3
203 parametersΔρmin = 0.39 e Å3
Crystal data top
C18H22N2O2V = 3344.8 (14) Å3
Mr = 298.38Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.714 (3) ŵ = 0.08 mm1
b = 8.430 (2) ÅT = 150 K
c = 33.872 (8) Å0.19 × 0.17 × 0.08 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
4178 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
2562 reflections with I > 2σ(I)
Tmin = 0.52, Tmax = 0.99Rint = 0.154
55300 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0770 restraints
wR(F2) = 0.248H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.37 e Å3
4178 reflectionsΔρmin = 0.39 e Å3
203 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
O10.99800 (14)0.2805 (2)0.01925 (5)0.0464 (6)
O20.64262 (13)0.22818 (19)0.10344 (5)0.0397 (5)
N10.84096 (15)0.1275 (2)0.06902 (5)0.0328 (6)
N20.76667 (16)0.0292 (2)0.08961 (5)0.0330 (6)
C11.0961 (2)0.3228 (4)0.00048 (8)0.0540 (10)
C21.1779 (2)0.2161 (4)0.00466 (8)0.0512 (9)
C31.1314 (2)0.0958 (3)0.02921 (7)0.0448 (8)
C41.0227 (2)0.1395 (3)0.03736 (6)0.0360 (7)
C50.93628 (19)0.0609 (3)0.06022 (6)0.0332 (7)
C60.67103 (19)0.0885 (3)0.10569 (6)0.0324 (7)
C70.59945 (19)0.0323 (3)0.12793 (7)0.0360 (7)
C80.4770 (2)0.0268 (4)0.11260 (8)0.0483 (9)
C90.6096 (2)0.0021 (3)0.17205 (7)0.0350 (7)
C100.5416 (2)0.1140 (3)0.19069 (7)0.0433 (8)
C110.5583 (2)0.1527 (3)0.23008 (7)0.0450 (8)
C120.6440 (2)0.0800 (3)0.25206 (7)0.0388 (7)
C130.7101 (2)0.0338 (3)0.23343 (7)0.0435 (8)
C140.6929 (2)0.0729 (3)0.19408 (7)0.0415 (8)
C150.6661 (2)0.1200 (3)0.29488 (7)0.0468 (9)
C160.6095 (2)0.0036 (3)0.32356 (7)0.0412 (8)
C170.4816 (2)0.0285 (3)0.32544 (8)0.0480 (9)
C180.6609 (3)0.0161 (5)0.36474 (9)0.0651 (13)
H11.104200.416400.015800.0650*
H21.252900.219400.006000.0610*
H2N0.786 (2)0.081 (3)0.0917 (7)0.037 (7)*
H31.169200.002900.038200.0540*
H50.950100.044200.069200.0400*
H70.631200.140400.122700.0430*
H8A0.430800.105400.126700.0720*
H8B0.445200.079300.117000.0720*
H8C0.476400.050800.084300.0720*
H100.482500.165100.176200.0520*
H110.510700.229800.242200.0540*
H130.768400.086300.247900.0520*
H140.739100.152100.182100.0500*
H15A0.749500.120200.299600.0560*
H15B0.637200.228300.300300.0560*
H160.623800.106300.313600.0490*
H17A0.449200.018800.298900.0720*
H17B0.447500.051700.342700.0720*
H17C0.465400.134500.335900.0720*
H18A0.743600.000200.363200.0970*
H18B0.645100.121600.375600.0970*
H18C0.627100.064900.381800.0970*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0561 (11)0.0513 (11)0.0318 (9)0.0040 (8)0.0054 (7)0.0101 (8)
O20.0468 (9)0.0360 (10)0.0364 (9)0.0030 (7)0.0081 (7)0.0032 (7)
N10.0397 (10)0.0379 (11)0.0209 (9)0.0040 (8)0.0003 (7)0.0038 (7)
N20.0397 (11)0.0316 (11)0.0277 (9)0.0017 (8)0.0035 (7)0.0046 (7)
C10.0674 (18)0.0610 (18)0.0335 (13)0.0139 (15)0.0133 (12)0.0083 (12)
C20.0536 (15)0.0672 (19)0.0327 (13)0.0138 (14)0.0121 (11)0.0043 (12)
C30.0488 (14)0.0530 (15)0.0326 (13)0.0032 (12)0.0078 (10)0.0013 (11)
C40.0460 (13)0.0406 (13)0.0213 (10)0.0040 (10)0.0015 (9)0.0011 (9)
C50.0415 (12)0.0381 (13)0.0199 (10)0.0033 (10)0.0014 (8)0.0021 (8)
C60.0395 (12)0.0347 (13)0.0230 (10)0.0029 (9)0.0005 (8)0.0003 (8)
C70.0403 (12)0.0346 (12)0.0332 (12)0.0030 (10)0.0062 (9)0.0006 (9)
C80.0463 (15)0.0582 (17)0.0403 (14)0.0085 (12)0.0037 (11)0.0045 (12)
C90.0401 (13)0.0350 (12)0.0300 (11)0.0033 (9)0.0082 (9)0.0035 (9)
C100.0500 (14)0.0441 (14)0.0358 (13)0.0087 (11)0.0040 (10)0.0021 (10)
C110.0578 (15)0.0421 (14)0.0351 (13)0.0074 (12)0.0088 (11)0.0005 (10)
C120.0461 (13)0.0403 (13)0.0299 (12)0.0091 (10)0.0073 (9)0.0022 (10)
C130.0419 (13)0.0541 (16)0.0345 (12)0.0024 (11)0.0032 (10)0.0066 (11)
C140.0409 (13)0.0454 (14)0.0381 (13)0.0062 (10)0.0074 (10)0.0017 (10)
C150.0509 (15)0.0574 (17)0.0320 (13)0.0134 (12)0.0038 (10)0.0020 (11)
C160.0483 (14)0.0474 (15)0.0280 (12)0.0007 (11)0.0033 (10)0.0024 (10)
C170.0485 (15)0.0580 (17)0.0376 (14)0.0012 (12)0.0062 (11)0.0019 (11)
C180.0608 (18)0.100 (3)0.0345 (15)0.0053 (17)0.0013 (13)0.0077 (14)
Geometric parameters (Å, º) top
O1—C11.376 (3)C16—C181.523 (4)
O1—C41.369 (3)C1—H10.9500
O2—C61.226 (3)C2—H20.9500
N1—N21.389 (2)C3—H30.9500
N1—C51.285 (3)C5—H50.9500
N2—C61.342 (3)C7—H71.0000
N2—H2N0.96 (3)C8—H8A0.9800
C1—C21.326 (4)C8—H8B0.9800
C2—C31.420 (4)C8—H8C0.9800
C3—C41.354 (3)C10—H100.9500
C4—C51.437 (3)C11—H110.9500
C6—C71.519 (3)C13—H130.9500
C7—C81.526 (3)C14—H140.9500
C7—C91.527 (3)C15—H15A0.9900
C9—C141.382 (3)C15—H15B0.9900
C9—C101.387 (3)C16—H161.0000
C10—C111.387 (3)C17—H17A0.9800
C11—C121.392 (3)C17—H17B0.9800
C12—C151.511 (3)C17—H17C0.9800
C12—C131.385 (3)C18—H18A0.9800
C13—C141.388 (3)C18—H18B0.9800
C15—C161.532 (3)C18—H18C0.9800
C16—C171.514 (3)
C1—O1—C4105.4 (2)C4—C5—H5119.00
N2—N1—C5113.59 (18)C6—C7—H7109.00
N1—N2—C6120.29 (18)C8—C7—H7108.00
C6—N2—H2N121.9 (14)C9—C7—H7109.00
N1—N2—H2N117.8 (14)C7—C8—H8A109.00
O1—C1—C2111.3 (3)C7—C8—H8B109.00
C1—C2—C3106.5 (2)C7—C8—H8C109.00
C2—C3—C4106.6 (2)H8A—C8—H8B109.00
O1—C4—C5119.6 (2)H8A—C8—H8C109.00
O1—C4—C3110.1 (2)H8B—C8—H8C110.00
C3—C4—C5130.3 (2)C9—C10—H10119.00
N1—C5—C4122.4 (2)C11—C10—H10119.00
O2—C6—C7121.7 (2)C10—C11—H11120.00
O2—C6—N2124.0 (2)C12—C11—H11120.00
N2—C6—C7114.4 (2)C12—C13—H13119.00
C6—C7—C9108.36 (19)C14—C13—H13119.00
C6—C7—C8109.3 (2)C9—C14—H14120.00
C8—C7—C9113.6 (2)C13—C14—H14120.00
C10—C9—C14118.1 (2)C12—C15—H15A109.00
C7—C9—C14119.8 (2)C12—C15—H15B109.00
C7—C9—C10122.0 (2)C16—C15—H15A109.00
C9—C10—C11121.1 (2)C16—C15—H15B109.00
C10—C11—C12120.8 (2)H15A—C15—H15B108.00
C11—C12—C15122.6 (2)C15—C16—H16108.00
C11—C12—C13117.7 (2)C17—C16—H16108.00
C13—C12—C15119.7 (2)C18—C16—H16108.00
C12—C13—C14121.4 (2)C16—C17—H17A109.00
C9—C14—C13120.8 (2)C16—C17—H17B109.00
C12—C15—C16113.1 (2)C16—C17—H17C109.00
C17—C16—C18110.1 (2)H17A—C17—H17B109.00
C15—C16—C17111.5 (2)H17A—C17—H17C109.00
C15—C16—C18111.4 (2)H17B—C17—H17C110.00
O1—C1—H1124.00C16—C18—H18A109.00
C2—C1—H1124.00C16—C18—H18B109.00
C1—C2—H2127.00C16—C18—H18C109.00
C3—C2—H2127.00H18A—C18—H18B110.00
C2—C3—H3127.00H18A—C18—H18C109.00
C4—C3—H3127.00H18B—C18—H18C110.00
N1—C5—H5119.00
C1—O1—C4—C5179.0 (2)C6—C7—C9—C1492.0 (3)
C4—O1—C1—C20.0 (3)C8—C7—C9—C1037.3 (3)
C1—O1—C4—C30.1 (3)C8—C7—C9—C14146.4 (2)
C5—N1—N2—C6170.46 (19)C7—C9—C10—C11174.8 (2)
N2—N1—C5—C4176.99 (19)C14—C9—C10—C111.6 (4)
N1—N2—C6—C7178.89 (17)C7—C9—C14—C13174.5 (2)
N1—N2—C6—O20.3 (3)C10—C9—C14—C131.9 (4)
O1—C1—C2—C30.1 (3)C9—C10—C11—C120.0 (4)
C1—C2—C3—C40.1 (3)C10—C11—C12—C131.2 (4)
C2—C3—C4—O10.1 (3)C10—C11—C12—C15179.2 (2)
C2—C3—C4—C5178.9 (2)C11—C12—C13—C140.9 (4)
O1—C4—C5—N19.8 (3)C15—C12—C13—C14179.5 (2)
C3—C4—C5—N1171.5 (2)C11—C12—C15—C1697.3 (3)
O2—C6—C7—C853.5 (3)C13—C12—C15—C1682.3 (3)
O2—C6—C7—C970.8 (3)C12—C13—C14—C90.7 (4)
N2—C6—C7—C8127.4 (2)C12—C15—C16—C1773.6 (3)
N2—C6—C7—C9108.4 (2)C12—C15—C16—C18163.0 (2)
C6—C7—C9—C1084.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O2i0.96 (3)1.86 (2)2.791 (2)164 (2)
C5—H5···O2i0.952.493.296 (3)142
Symmetry code: (i) x+3/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O2i0.96 (3)1.86 (2)2.791 (2)164 (2)
C5—H5···O2i0.952.493.296 (3)142
Symmetry code: (i) x+3/2, y+1/2, z.
 

Acknowledgements

Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study. The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer is gratefully acknowledged.

References

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