N'-[(E)-(Furan-2-yl)methyl-idene]-2-[4-(2-methyl-prop-yl)phen-yl]propano-hydrazide.

In the title mol-ecule, 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 mol-ecules 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 ▶, 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 = 298.38

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 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

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814003936/hg5385sup1.cif

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

Click here for additional data file.

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

CCDC reference: 987953

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H22N2O2	F(000) = 1280
Mr = 298.38	Dx = 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

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

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(Fo2) + (0.1555P)2 + 0.1359P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
4178 reflections	Δρmax = 0.37 e Å−3
203 parameters	Δρmin = −0.39 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .