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

Akkurt, M.; Mohamed, S.K.; Mague, J.T.; Albayati, M.R.; Younes, S.H.H.

doi:10.1107/S1600536814003936

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 3| March 2014| Page o356

doi:10.1107/S1600536814003936

Open

access

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

Mehmet Akkurt,^a Shaaban K. Mohamed,^b,^c Joel T. Mague,^d Mustafa R. Albayati ^e ^* and Sabry H. H. Younes ^f

^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].

CCDC reference: 987953

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 , 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

Crystal data

C₁₈H₂₂N₂O₂
M_r = 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 ) T_min = 0.52, T_max = 0.99
55300 measured reflections
4178 independent reflections
2562 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; 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 ).

Supporting information

CCDC reference: 987953

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814003936/hg5385sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814003936/hg5385Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814003936/hg5385Isup3.cml

checkCIF report

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.

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

	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.
	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

C₁₈H₂₂N₂O₂	F(000) = 1280
M_r = 298.38	D_x = 1.185 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9972 reflections
a = 11.714 (3) Å	θ = 2.4–28.2°
b = 8.430 (2) Å	µ = 0.08 mm⁻¹
c = 33.872 (8) Å	T = 150 K
V = 3344.8 (14) Å³	Slab, clear orange
Z = 8	0.19 × 0.17 × 0.08 mm

Data collection top

Bruker SMART APEX CCD diffractometer	4178 independent reflections
Radiation source: fine-focus sealed tube	2562 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.154
Detector resolution: 8.3660 pixels mm^-1	θ_max = 28.4°, θ_min = 2.1°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −11→11
T_min = 0.52, T_max = 0.99	l = −45→45
55300 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.077	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.248	w = 1/[σ²(F_o²) + (0.1555P)² + 0.1359P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4178 reflections	Δρ_max = 0.37 e Å⁻³
203 parameters	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₈H₂₂N₂O₂	V = 3344.8 (14) Å³
M_r = 298.38	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.714 (3) Å	µ = 0.08 mm⁻¹
b = 8.430 (2) Å	T = 150 K
c = 33.872 (8) Å	0.19 × 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)
T_min = 0.52, T_max = 0.99	R_int = 0.154
55300 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.248	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.37 e Å⁻³
4178 reflections	Δρ_min = −0.39 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O1	0.99800 (14)	−0.2805 (2)	0.01925 (5)	0.0464 (6)
O2	0.64262 (13)	−0.22818 (19)	0.10344 (5)	0.0397 (5)
N1	0.84096 (15)	−0.1275 (2)	0.06902 (5)	0.0328 (6)
N2	0.76667 (16)	−0.0292 (2)	0.08961 (5)	0.0330 (6)
C1	1.0961 (2)	−0.3228 (4)	−0.00048 (8)	0.0540 (10)
C2	1.1779 (2)	−0.2161 (4)	0.00466 (8)	0.0512 (9)
C3	1.1314 (2)	−0.0958 (3)	0.02921 (7)	0.0448 (8)
C4	1.0227 (2)	−0.1395 (3)	0.03736 (6)	0.0360 (7)
C5	0.93628 (19)	−0.0609 (3)	0.06022 (6)	0.0332 (7)
C6	0.67103 (19)	−0.0885 (3)	0.10569 (6)	0.0324 (7)
C7	0.59945 (19)	0.0323 (3)	0.12793 (7)	0.0360 (7)
C8	0.4770 (2)	0.0268 (4)	0.11260 (8)	0.0483 (9)
C9	0.6096 (2)	−0.0021 (3)	0.17205 (7)	0.0350 (7)
C10	0.5416 (2)	−0.1140 (3)	0.19069 (7)	0.0433 (8)
C11	0.5583 (2)	−0.1527 (3)	0.23008 (7)	0.0450 (8)
C12	0.6440 (2)	−0.0800 (3)	0.25206 (7)	0.0388 (7)
C13	0.7101 (2)	0.0338 (3)	0.23343 (7)	0.0435 (8)
C14	0.6929 (2)	0.0729 (3)	0.19408 (7)	0.0415 (8)
C15	0.6661 (2)	−0.1200 (3)	0.29488 (7)	0.0468 (9)
C16	0.6095 (2)	−0.0036 (3)	0.32356 (7)	0.0412 (8)
C17	0.4816 (2)	−0.0285 (3)	0.32544 (8)	0.0480 (9)
C18	0.6609 (3)	−0.0161 (5)	0.36474 (9)	0.0651 (13)
H1	1.10420	−0.41640	−0.01580	0.0650*
H2	1.25290	−0.21940	−0.00600	0.0610*
H2N	0.786 (2)	0.081 (3)	0.0917 (7)	0.037 (7)*
H3	1.16920	−0.00290	0.03820	0.0540*
H5	0.95010	0.04420	0.06920	0.0400*
H7	0.63120	0.14040	0.12270	0.0430*
H8A	0.43080	0.10540	0.12670	0.0720*
H8B	0.44520	−0.07930	0.11700	0.0720*
H8C	0.47640	0.05080	0.08430	0.0720*
H10	0.48250	−0.16510	0.17620	0.0520*
H11	0.51070	−0.22980	0.24220	0.0540*
H13	0.76840	0.08630	0.24790	0.0520*
H14	0.73910	0.15210	0.18210	0.0500*
H15A	0.74950	−0.12020	0.29960	0.0560*
H15B	0.63720	−0.22830	0.30030	0.0560*
H16	0.62380	0.10630	0.31360	0.0490*
H17A	0.44920	−0.01880	0.29890	0.0720*
H17B	0.44750	0.05170	0.34270	0.0720*
H17C	0.46540	−0.13450	0.33590	0.0720*
H18A	0.74360	0.00020	0.36320	0.0970*
H18B	0.64510	−0.12160	0.37560	0.0970*
H18C	0.62710	0.06490	0.38180	0.0970*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0561 (11)	0.0513 (11)	0.0318 (9)	0.0040 (8)	0.0054 (7)	−0.0101 (8)
O2	0.0468 (9)	0.0360 (10)	0.0364 (9)	−0.0030 (7)	0.0081 (7)	−0.0032 (7)
N1	0.0397 (10)	0.0379 (11)	0.0209 (9)	0.0040 (8)	0.0003 (7)	−0.0038 (7)
N2	0.0397 (11)	0.0316 (11)	0.0277 (9)	0.0017 (8)	0.0035 (7)	−0.0046 (7)
C1	0.0674 (18)	0.0610 (18)	0.0335 (13)	0.0139 (15)	0.0133 (12)	−0.0083 (12)
C2	0.0536 (15)	0.0672 (19)	0.0327 (13)	0.0138 (14)	0.0121 (11)	0.0043 (12)
C3	0.0488 (14)	0.0530 (15)	0.0326 (13)	0.0032 (12)	0.0078 (10)	0.0013 (11)
C4	0.0460 (13)	0.0406 (13)	0.0213 (10)	0.0040 (10)	0.0015 (9)	0.0011 (9)
C5	0.0415 (12)	0.0381 (13)	0.0199 (10)	0.0033 (10)	−0.0014 (8)	−0.0021 (8)
C6	0.0395 (12)	0.0347 (13)	0.0230 (10)	0.0029 (9)	−0.0005 (8)	0.0003 (8)
C7	0.0403 (12)	0.0346 (12)	0.0332 (12)	0.0030 (10)	0.0062 (9)	0.0006 (9)
C8	0.0463 (15)	0.0582 (17)	0.0403 (14)	0.0085 (12)	0.0037 (11)	0.0045 (12)
C9	0.0401 (13)	0.0350 (12)	0.0300 (11)	0.0033 (9)	0.0082 (9)	−0.0035 (9)
C10	0.0500 (14)	0.0441 (14)	0.0358 (13)	−0.0087 (11)	0.0040 (10)	−0.0021 (10)
C11	0.0578 (15)	0.0421 (14)	0.0351 (13)	−0.0074 (12)	0.0088 (11)	0.0005 (10)
C12	0.0461 (13)	0.0403 (13)	0.0299 (12)	0.0091 (10)	0.0073 (9)	−0.0022 (10)
C13	0.0419 (13)	0.0541 (16)	0.0345 (12)	−0.0024 (11)	0.0032 (10)	−0.0066 (11)
C14	0.0409 (13)	0.0454 (14)	0.0381 (13)	−0.0062 (10)	0.0074 (10)	−0.0017 (10)
C15	0.0509 (15)	0.0574 (17)	0.0320 (13)	0.0134 (12)	0.0038 (10)	0.0020 (11)
C16	0.0483 (14)	0.0474 (15)	0.0280 (12)	−0.0007 (11)	0.0033 (10)	−0.0024 (10)
C17	0.0485 (15)	0.0580 (17)	0.0376 (14)	0.0012 (12)	0.0062 (11)	−0.0019 (11)
C18	0.0608 (18)	0.100 (3)	0.0345 (15)	−0.0053 (17)	−0.0013 (13)	−0.0077 (14)

Geometric parameters (Å, º) top

O1—C1	1.376 (3)	C16—C18	1.523 (4)
O1—C4	1.369 (3)	C1—H1	0.9500
O2—C6	1.226 (3)	C2—H2	0.9500
N1—N2	1.389 (2)	C3—H3	0.9500
N1—C5	1.285 (3)	C5—H5	0.9500
N2—C6	1.342 (3)	C7—H7	1.0000
N2—H2N	0.96 (3)	C8—H8A	0.9800
C1—C2	1.326 (4)	C8—H8B	0.9800
C2—C3	1.420 (4)	C8—H8C	0.9800
C3—C4	1.354 (3)	C10—H10	0.9500
C4—C5	1.437 (3)	C11—H11	0.9500
C6—C7	1.519 (3)	C13—H13	0.9500
C7—C8	1.526 (3)	C14—H14	0.9500
C7—C9	1.527 (3)	C15—H15A	0.9900
C9—C14	1.382 (3)	C15—H15B	0.9900
C9—C10	1.387 (3)	C16—H16	1.0000
C10—C11	1.387 (3)	C17—H17A	0.9800
C11—C12	1.392 (3)	C17—H17B	0.9800
C12—C15	1.511 (3)	C17—H17C	0.9800
C12—C13	1.385 (3)	C18—H18A	0.9800
C13—C14	1.388 (3)	C18—H18B	0.9800
C15—C16	1.532 (3)	C18—H18C	0.9800
C16—C17	1.514 (3)

C1—O1—C4	105.4 (2)	C4—C5—H5	119.00
N2—N1—C5	113.59 (18)	C6—C7—H7	109.00
N1—N2—C6	120.29 (18)	C8—C7—H7	108.00
C6—N2—H2N	121.9 (14)	C9—C7—H7	109.00
N1—N2—H2N	117.8 (14)	C7—C8—H8A	109.00
O1—C1—C2	111.3 (3)	C7—C8—H8B	109.00
C1—C2—C3	106.5 (2)	C7—C8—H8C	109.00
C2—C3—C4	106.6 (2)	H8A—C8—H8B	109.00
O1—C4—C5	119.6 (2)	H8A—C8—H8C	109.00
O1—C4—C3	110.1 (2)	H8B—C8—H8C	110.00
C3—C4—C5	130.3 (2)	C9—C10—H10	119.00
N1—C5—C4	122.4 (2)	C11—C10—H10	119.00
O2—C6—C7	121.7 (2)	C10—C11—H11	120.00
O2—C6—N2	124.0 (2)	C12—C11—H11	120.00
N2—C6—C7	114.4 (2)	C12—C13—H13	119.00
C6—C7—C9	108.36 (19)	C14—C13—H13	119.00
C6—C7—C8	109.3 (2)	C9—C14—H14	120.00
C8—C7—C9	113.6 (2)	C13—C14—H14	120.00
C10—C9—C14	118.1 (2)	C12—C15—H15A	109.00
C7—C9—C14	119.8 (2)	C12—C15—H15B	109.00
C7—C9—C10	122.0 (2)	C16—C15—H15A	109.00
C9—C10—C11	121.1 (2)	C16—C15—H15B	109.00
C10—C11—C12	120.8 (2)	H15A—C15—H15B	108.00
C11—C12—C15	122.6 (2)	C15—C16—H16	108.00
C11—C12—C13	117.7 (2)	C17—C16—H16	108.00
C13—C12—C15	119.7 (2)	C18—C16—H16	108.00
C12—C13—C14	121.4 (2)	C16—C17—H17A	109.00
C9—C14—C13	120.8 (2)	C16—C17—H17B	109.00
C12—C15—C16	113.1 (2)	C16—C17—H17C	109.00
C17—C16—C18	110.1 (2)	H17A—C17—H17B	109.00
C15—C16—C17	111.5 (2)	H17A—C17—H17C	109.00
C15—C16—C18	111.4 (2)	H17B—C17—H17C	110.00
O1—C1—H1	124.00	C16—C18—H18A	109.00
C2—C1—H1	124.00	C16—C18—H18B	109.00
C1—C2—H2	127.00	C16—C18—H18C	109.00
C3—C2—H2	127.00	H18A—C18—H18B	110.00
C2—C3—H3	127.00	H18A—C18—H18C	109.00
C4—C3—H3	127.00	H18B—C18—H18C	110.00
N1—C5—H5	119.00

C1—O1—C4—C5	179.0 (2)	C6—C7—C9—C14	92.0 (3)
C4—O1—C1—C2	0.0 (3)	C8—C7—C9—C10	37.3 (3)
C1—O1—C4—C3	0.1 (3)	C8—C7—C9—C14	−146.4 (2)
C5—N1—N2—C6	−170.46 (19)	C7—C9—C10—C11	174.8 (2)
N2—N1—C5—C4	−176.99 (19)	C14—C9—C10—C11	−1.6 (4)
N1—N2—C6—C7	178.89 (17)	C7—C9—C14—C13	−174.5 (2)
N1—N2—C6—O2	−0.3 (3)	C10—C9—C14—C13	1.9 (4)
O1—C1—C2—C3	−0.1 (3)	C9—C10—C11—C12	0.0 (4)
C1—C2—C3—C4	0.1 (3)	C10—C11—C12—C13	1.2 (4)
C2—C3—C4—O1	−0.1 (3)	C10—C11—C12—C15	−179.2 (2)
C2—C3—C4—C5	−178.9 (2)	C11—C12—C13—C14	−0.9 (4)
O1—C4—C5—N1	9.8 (3)	C15—C12—C13—C14	179.5 (2)
C3—C4—C5—N1	−171.5 (2)	C11—C12—C15—C16	−97.3 (3)
O2—C6—C7—C8	−53.5 (3)	C13—C12—C15—C16	82.3 (3)
O2—C6—C7—C9	70.8 (3)	C12—C13—C14—C9	−0.7 (4)
N2—C6—C7—C8	127.4 (2)	C12—C15—C16—C17	73.6 (3)
N2—C6—C7—C9	−108.4 (2)	C12—C15—C16—C18	−163.0 (2)
C6—C7—C9—C10	−84.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+3/2, y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+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

Agrawal, N., Chandrasekar, M. J. N., Sara, U. V. S. & Rohini, A. (2010). Int. J. Drug Deliv. Technol. 2, 12–17. Google Scholar
Alert, A. (1958). Nature, 182, 421–423. PubMed Web of Science Google Scholar
Asif, H. (2009). Acta Pol. Pharm. Drug Res. 66, 513–521. Google Scholar
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bundgaard, H. (1991). Drugs Future, 16, 443–458. Google Scholar
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. CrossRef Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
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. CAS Google Scholar
Mohamed, S. K., Albayati, M. R., Younes, S. H. H. & Abed-Alkareem, M. G. (2013). CSJ, CSJ-97. Google Scholar
Neeraj, A., Chandrasekar, M. J. N., Sara, U. V. S. & Rohini, A. (2010). Int. J. Drug Deliv. Technol. 2, 12–17. Google Scholar
Parmeshwari, K. H., Murumkar, P. R., Giridhar, R. & Yadav, M. R. (2009). Mini Rev. Med. Chem. 9, 124–139. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 3| March 2014| Page o356

doi:10.1107/S1600536814003936

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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