organic compounds
(E)-N′-(4-Methoxybenzylidene)-2-m-tolylacetohydrazide
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
*Correspondence e-mail: jjasinski@keene.edu
In the title molecule, C17H18N2O2, the benzene rings form a dihedral angle of 83.0 (7)°. In the crystal, N—H⋯O hydrogen bonds, in an R22(8) graph-set motif, link molecules into centrocymmetric dimers, and weak C—H⋯π interactions further link these dimers into columns in [100].
Related literature
For the biological activity of et al. (2001); El-Masry et al. (2000); Hodnett & Dunn (1970); Pandey et al. (1999); Singh & Dash (1988). For employed as ligands for complexation of metal ions, see: Aydogan et al. (2001). For with applications in dyes and pigments, see: Taggi et al. (2002). For related structures, see: Akkurt et al. (2011); Lv et al. (2009a,b); Yu & Lv (2010). For standard bond lengths, see: Allen et al. (1987).
see: DesaiExperimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536812047113/cv5364sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047113/cv5364Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812047113/cv5364Isup3.cml
To a stirred solution of 2-m-tolylacetohydrazide (1 g, 6.09 mmol) in ethanol (10 mL), 4-methoxybenzaldehyde (0.79 g, 6.09 mmol) was added (Fig. 3) and strirred at room temperature for 30 minutes. Precipitated solid was filtered and dried. The single crystal was grown from ethyl acetate by slow evaporation method and yield of the compound was 94% (m.p.: 403-405 K).
All H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.93Å (CH), 0.97Å (CH2), 0.96Å (CH3) or 0.86Å (NH). Isotropic displacement parameters for these atoms were set to 1.19-1.21 (CH, CH2), 1.49 (CH3) or 1.21 (NH) times Ueq of the parent atom.
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C17H18N2O2 | Z = 2 |
Mr = 282.33 | F(000) = 300 |
Triclinic, P1 | Dx = 1.270 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 6.4961 (8) Å | Cell parameters from 1237 reflections |
b = 9.8047 (10) Å | θ = 3.8–72.4° |
c = 12.7464 (13) Å | µ = 0.68 mm−1 |
α = 112.130 (9)° | T = 173 K |
β = 95.507 (10)° | Chunk, colorless |
γ = 96.601 (9)° | 0.34 × 0.14 × 0.06 mm |
V = 738.45 (14) Å3 |
Oxford Diffraction Xcalibur Eos Gemini diffractometer | 2840 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2032 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 72.6°, θmin = 3.8° |
ω scans | h = −8→7 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −12→8 |
Tmin = 0.735, Tmax = 1.000 | l = −11→15 |
4418 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.158 | w = 1/[σ2(Fo2) + (0.064P)2 + 0.071P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2840 reflections | Δρmax = 0.21 e Å−3 |
193 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0097 (12) |
C17H18N2O2 | γ = 96.601 (9)° |
Mr = 282.33 | V = 738.45 (14) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.4961 (8) Å | Cu Kα radiation |
b = 9.8047 (10) Å | µ = 0.68 mm−1 |
c = 12.7464 (13) Å | T = 173 K |
α = 112.130 (9)° | 0.34 × 0.14 × 0.06 mm |
β = 95.507 (10)° |
Oxford Diffraction Xcalibur Eos Gemini diffractometer | 2840 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 2032 reflections with I > 2σ(I) |
Tmin = 0.735, Tmax = 1.000 | Rint = 0.034 |
4418 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.21 e Å−3 |
2840 reflections | Δρmin = −0.20 e Å−3 |
193 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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 | 0.4694 (2) | 0.19694 (16) | 0.05426 (13) | 0.0429 (4) | |
O2 | 1.6491 (2) | −0.04156 (17) | −0.38486 (13) | 0.0482 (4) | |
N1 | 0.7161 (2) | 0.09164 (19) | −0.04553 (14) | 0.0363 (4) | |
H1 | 0.6645 | 0.0052 | −0.0486 | 0.044* | |
N2 | 0.8879 (2) | 0.10557 (19) | −0.09800 (14) | 0.0365 (4) | |
C1 | 0.6266 (3) | 0.2111 (2) | 0.01087 (17) | 0.0376 (5) | |
C2 | 0.7332 (4) | 0.3634 (2) | 0.02237 (19) | 0.0447 (5) | |
H2A | 0.8138 | 0.3528 | −0.0397 | 0.054* | |
H2B | 0.6288 | 0.4255 | 0.0188 | 0.054* | |
C3 | 0.8763 (3) | 0.4349 (2) | 0.13628 (19) | 0.0397 (5) | |
C4 | 1.0802 (4) | 0.4059 (2) | 0.1471 (2) | 0.0488 (6) | |
H4 | 1.1354 | 0.3504 | 0.0826 | 0.059* | |
C5 | 1.2004 (4) | 0.4600 (3) | 0.2543 (3) | 0.0584 (7) | |
H5 | 1.3365 | 0.4402 | 0.2617 | 0.070* | |
C6 | 1.1199 (4) | 0.5432 (3) | 0.3507 (3) | 0.0596 (7) | |
H6 | 1.2023 | 0.5784 | 0.4222 | 0.071* | |
C7 | 0.9182 (4) | 0.5748 (2) | 0.3419 (2) | 0.0487 (6) | |
C8 | 0.7994 (3) | 0.5198 (2) | 0.2336 (2) | 0.0419 (5) | |
H8 | 0.6640 | 0.5408 | 0.2262 | 0.050* | |
C9 | 0.9579 (3) | −0.0161 (2) | −0.14981 (17) | 0.0353 (5) | |
H9 | 0.8927 | −0.1052 | −0.1490 | 0.042* | |
C10 | 1.1381 (3) | −0.0163 (2) | −0.20977 (16) | 0.0336 (4) | |
C11 | 1.2404 (3) | 0.1120 (2) | −0.21651 (17) | 0.0365 (5) | |
H11 | 1.1929 | 0.2020 | −0.1818 | 0.044* | |
C12 | 1.4114 (3) | 0.1087 (2) | −0.27377 (18) | 0.0376 (5) | |
H12 | 1.4781 | 0.1958 | −0.2771 | 0.045* | |
C13 | 1.4832 (3) | −0.0259 (2) | −0.32644 (17) | 0.0362 (5) | |
C14 | 1.3827 (3) | −0.1543 (2) | −0.31983 (18) | 0.0403 (5) | |
H14 | 1.4310 | −0.2441 | −0.3541 | 0.048* | |
C15 | 1.2124 (3) | −0.1503 (2) | −0.26320 (17) | 0.0379 (5) | |
H15 | 1.1458 | −0.2377 | −0.2603 | 0.045* | |
C16 | 1.7630 (3) | 0.0894 (3) | −0.3878 (2) | 0.0523 (6) | |
H16A | 1.6733 | 0.1318 | −0.4272 | 0.078* | |
H16B | 1.8807 | 0.0643 | −0.4272 | 0.078* | |
H16C | 1.8118 | 0.1605 | −0.3109 | 0.078* | |
C17 | 0.8251 (5) | 0.6648 (3) | 0.4450 (2) | 0.0709 (8) | |
H17A | 0.7722 | 0.7457 | 0.4325 | 0.106* | |
H17B | 0.9312 | 0.7039 | 0.5114 | 0.106* | |
H17C | 0.7128 | 0.6020 | 0.4568 | 0.106* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0382 (8) | 0.0476 (9) | 0.0442 (8) | 0.0160 (7) | 0.0149 (7) | 0.0148 (7) |
O2 | 0.0452 (9) | 0.0510 (10) | 0.0483 (9) | 0.0128 (7) | 0.0216 (7) | 0.0144 (7) |
N1 | 0.0370 (9) | 0.0360 (9) | 0.0391 (9) | 0.0108 (7) | 0.0137 (7) | 0.0150 (7) |
N2 | 0.0349 (9) | 0.0411 (10) | 0.0373 (9) | 0.0126 (7) | 0.0123 (7) | 0.0163 (8) |
C1 | 0.0375 (11) | 0.0448 (12) | 0.0347 (10) | 0.0177 (9) | 0.0081 (9) | 0.0164 (9) |
C2 | 0.0544 (13) | 0.0416 (12) | 0.0501 (13) | 0.0228 (10) | 0.0188 (10) | 0.0245 (10) |
C3 | 0.0438 (12) | 0.0301 (10) | 0.0523 (13) | 0.0117 (9) | 0.0164 (10) | 0.0204 (9) |
C4 | 0.0453 (13) | 0.0380 (12) | 0.0692 (16) | 0.0117 (10) | 0.0231 (12) | 0.0232 (11) |
C5 | 0.0348 (12) | 0.0457 (14) | 0.096 (2) | 0.0049 (10) | 0.0052 (13) | 0.0307 (14) |
C6 | 0.0587 (16) | 0.0412 (13) | 0.0705 (18) | −0.0021 (11) | −0.0082 (13) | 0.0199 (12) |
C7 | 0.0599 (14) | 0.0317 (11) | 0.0513 (14) | 0.0062 (10) | 0.0098 (11) | 0.0127 (10) |
C8 | 0.0418 (12) | 0.0312 (10) | 0.0584 (14) | 0.0134 (9) | 0.0173 (10) | 0.0194 (10) |
C9 | 0.0378 (11) | 0.0337 (10) | 0.0366 (10) | 0.0095 (8) | 0.0089 (8) | 0.0144 (8) |
C10 | 0.0347 (10) | 0.0361 (10) | 0.0310 (10) | 0.0106 (8) | 0.0071 (8) | 0.0126 (8) |
C11 | 0.0397 (11) | 0.0330 (10) | 0.0391 (11) | 0.0134 (8) | 0.0097 (9) | 0.0135 (9) |
C12 | 0.0389 (11) | 0.0360 (11) | 0.0403 (11) | 0.0089 (8) | 0.0086 (9) | 0.0160 (9) |
C13 | 0.0348 (10) | 0.0428 (11) | 0.0310 (10) | 0.0098 (8) | 0.0075 (8) | 0.0130 (9) |
C14 | 0.0429 (12) | 0.0357 (11) | 0.0405 (11) | 0.0149 (9) | 0.0126 (9) | 0.0091 (9) |
C15 | 0.0426 (11) | 0.0320 (10) | 0.0400 (11) | 0.0095 (8) | 0.0103 (9) | 0.0132 (9) |
C16 | 0.0429 (13) | 0.0643 (16) | 0.0530 (14) | 0.0051 (11) | 0.0186 (11) | 0.0249 (12) |
C17 | 0.096 (2) | 0.0541 (16) | 0.0542 (16) | 0.0169 (15) | 0.0162 (15) | 0.0096 (13) |
O1—C1 | 1.225 (2) | C7—C17 | 1.508 (3) |
O2—C13 | 1.358 (2) | C8—H8 | 0.9300 |
O2—C16 | 1.422 (3) | C9—C10 | 1.457 (3) |
N1—C1 | 1.352 (2) | C9—H9 | 0.9300 |
N1—N2 | 1.374 (2) | C10—C11 | 1.390 (3) |
N1—H1 | 0.8600 | C10—C15 | 1.399 (3) |
N2—C9 | 1.286 (2) | C11—C12 | 1.383 (3) |
C1—C2 | 1.520 (3) | C11—H11 | 0.9300 |
C2—C3 | 1.513 (3) | C12—C13 | 1.394 (3) |
C2—H2A | 0.9700 | C12—H12 | 0.9300 |
C2—H2B | 0.9700 | C13—C14 | 1.386 (3) |
C3—C8 | 1.385 (3) | C14—C15 | 1.374 (3) |
C3—C4 | 1.391 (3) | C14—H14 | 0.9300 |
C4—C5 | 1.383 (4) | C15—H15 | 0.9300 |
C4—H4 | 0.9300 | C16—H16A | 0.9600 |
C5—C6 | 1.383 (4) | C16—H16B | 0.9600 |
C5—H5 | 0.9300 | C16—H16C | 0.9600 |
C6—C7 | 1.384 (3) | C17—H17A | 0.9600 |
C6—H6 | 0.9300 | C17—H17B | 0.9600 |
C7—C8 | 1.389 (3) | C17—H17C | 0.9600 |
C13—O2—C16 | 117.66 (17) | N2—C9—H9 | 119.5 |
C1—N1—N2 | 121.37 (17) | C10—C9—H9 | 119.5 |
C1—N1—H1 | 119.3 | C11—C10—C15 | 118.04 (18) |
N2—N1—H1 | 119.3 | C11—C10—C9 | 122.64 (18) |
C9—N2—N1 | 115.66 (17) | C15—C10—C9 | 119.32 (18) |
O1—C1—N1 | 121.0 (2) | C12—C11—C10 | 121.44 (18) |
O1—C1—C2 | 121.47 (18) | C12—C11—H11 | 119.3 |
N1—C1—C2 | 117.52 (18) | C10—C11—H11 | 119.3 |
C3—C2—C1 | 108.30 (17) | C11—C12—C13 | 119.67 (19) |
C3—C2—H2A | 110.0 | C11—C12—H12 | 120.2 |
C1—C2—H2A | 110.0 | C13—C12—H12 | 120.2 |
C3—C2—H2B | 110.0 | O2—C13—C14 | 116.24 (18) |
C1—C2—H2B | 110.0 | O2—C13—C12 | 124.44 (19) |
H2A—C2—H2B | 108.4 | C14—C13—C12 | 119.32 (19) |
C8—C3—C4 | 118.9 (2) | C15—C14—C13 | 120.69 (19) |
C8—C3—C2 | 119.98 (19) | C15—C14—H14 | 119.7 |
C4—C3—C2 | 120.8 (2) | C13—C14—H14 | 119.7 |
C5—C4—C3 | 119.6 (2) | C14—C15—C10 | 120.84 (19) |
C5—C4—H4 | 120.2 | C14—C15—H15 | 119.6 |
C3—C4—H4 | 120.2 | C10—C15—H15 | 119.6 |
C4—C5—C6 | 120.6 (2) | O2—C16—H16A | 109.5 |
C4—C5—H5 | 119.7 | O2—C16—H16B | 109.5 |
C6—C5—H5 | 119.7 | H16A—C16—H16B | 109.5 |
C5—C6—C7 | 120.8 (3) | O2—C16—H16C | 109.5 |
C5—C6—H6 | 119.6 | H16A—C16—H16C | 109.5 |
C7—C6—H6 | 119.6 | H16B—C16—H16C | 109.5 |
C6—C7—C8 | 117.9 (2) | C7—C17—H17A | 109.5 |
C6—C7—C17 | 122.3 (3) | C7—C17—H17B | 109.5 |
C8—C7—C17 | 119.8 (2) | H17A—C17—H17B | 109.5 |
C3—C8—C7 | 122.1 (2) | C7—C17—H17C | 109.5 |
C3—C8—H8 | 119.0 | H17A—C17—H17C | 109.5 |
C7—C8—H8 | 119.0 | H17B—C17—H17C | 109.5 |
N2—C9—C10 | 120.92 (18) | ||
C1—N1—N2—C9 | −179.39 (18) | C17—C7—C8—C3 | −179.1 (2) |
N2—N1—C1—O1 | 177.62 (17) | N1—N2—C9—C10 | 179.35 (16) |
N2—N1—C1—C2 | −4.8 (3) | N2—C9—C10—C11 | −1.4 (3) |
O1—C1—C2—C3 | 83.1 (2) | N2—C9—C10—C15 | 178.72 (18) |
N1—C1—C2—C3 | −94.5 (2) | C15—C10—C11—C12 | −0.2 (3) |
C1—C2—C3—C8 | −88.4 (2) | C9—C10—C11—C12 | 179.85 (18) |
C1—C2—C3—C4 | 85.9 (2) | C10—C11—C12—C13 | 0.2 (3) |
C8—C3—C4—C5 | 1.0 (3) | C16—O2—C13—C14 | −176.56 (19) |
C2—C3—C4—C5 | −173.3 (2) | C16—O2—C13—C12 | 3.1 (3) |
C3—C4—C5—C6 | −0.3 (3) | C11—C12—C13—O2 | 179.91 (18) |
C4—C5—C6—C7 | −0.3 (4) | C11—C12—C13—C14 | −0.5 (3) |
C5—C6—C7—C8 | 0.3 (4) | O2—C13—C14—C15 | −179.62 (18) |
C5—C6—C7—C17 | 179.8 (2) | C12—C13—C14—C15 | 0.7 (3) |
C4—C3—C8—C7 | −1.2 (3) | C13—C14—C15—C10 | −0.7 (3) |
C2—C3—C8—C7 | 173.23 (19) | C11—C10—C15—C14 | 0.5 (3) |
C6—C7—C8—C3 | 0.5 (3) | C9—C10—C15—C14 | −179.58 (18) |
Cg is the centroid of the C3–C8 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.04 | 2.902 (2) | 178 |
C15—H15···Cgii | 0.93 | 2.63 | 3.557 (2) | 173 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C17H18N2O2 |
Mr | 282.33 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 6.4961 (8), 9.8047 (10), 12.7464 (13) |
α, β, γ (°) | 112.130 (9), 95.507 (10), 96.601 (9) |
V (Å3) | 738.45 (14) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 0.68 |
Crystal size (mm) | 0.34 × 0.14 × 0.06 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Eos Gemini diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.735, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4418, 2840, 2032 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.619 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.158, 1.04 |
No. of reflections | 2840 |
No. of parameters | 193 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.20 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Cg is the centroid of the C3–C8 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.04 | 2.902 (2) | 177.6 |
C15—H15···Cgii | 0.93 | 2.63 | 3.557 (2) | 173.0 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y, −z. |
Acknowledgements
ASP thanks UOM for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.
References
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Schiff bases are known to have biological activities such as antimicrobial (El-Masry et al., 2000; Pandey et al., 1999), antifungal (Singh et al., 1988), antitumor (Hodnett et al., 1970; Desai et al., 2001), and as herbicides. Schiff bases have also been employed as ligands for complexation of metal ions (Aydogan et al., 2001). On the industrial scale, they have wide range of applications such as dyes and pigments (Taggi et al., 2002). The crystal structures of some Schiff base hydrazines, viz., N'-(2-methoxybenzylidene) acetohydrazide (Yu & Lv, 2010), 2-[6-(4-chlorophenyl)imidazo[2,1-b][1,3] thiazol-2-yl]-N'-[(E)-4-methoxybenzylidene]acetohydrazide (Akkurt et al., 2011), N'-(3-methoxybenzylidene)acetohydrazide and N'-(3,4-dimethoxybenzylidene)acetohydrazide (Lv et al., 2009a,b). In view of the importance of hydrazides, the crystal structure of title compound (I) is reported.
In the title molecule, C17H18N2O2, two benzene rings form a dihedral angle of 83.0 (7)° (Fig. 1). Bond lengths are in normal ranges (Allen, 1987). In the crystal, N—H···O hydrogen bonds (Table 1), in an R22(8) graph set motif, link molecules into centrocymmetric dimers, and weak C–H···π interactions (Table 1) link further these dimers into columns in [100] (Fig. 2).