organic compounds
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
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 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).
in the synthesis of potential bio-active pharmacophors, see: MohamedExperimental
Crystal data
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Data collection: APEX2 (Bruker, 2013); cell 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
10.1107/S1600536814003936/hg5385sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814003936/hg5385Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814003936/hg5385Isup3.cml
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.
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).
Data collection: APEX2 (Bruker, 2013); cell
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).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 |
C18H22N2O2 | V = 3344.8 (14) Å3 |
Mr = 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 |
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 = 0.99 | Rint = 0.154 |
55300 measured reflections |
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 | Δρmax = 0.37 e Å−3 |
4178 reflections | Δρmin = −0.39 e Å−3 |
203 parameters |
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 |
Symmetry code: (i) −x+3/2, y+1/2, z. |
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.
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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.