organic compounds
5-((Methoxyimino){2-[(2-methylphenoxy)methyl]phenyl}methyl)-N-phenyl-1,3,4-oxadiazol-2-amine
aPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and bNational Research Centre for Grapes, Pune 412 307, India
*Correspondence e-mail: rkvk.paper11@gmail.com
In the title molecule, C24H22N4O3, the plane of the oxadiazole ring forms a dihedral angle of 32.41 (12)° with that of the phenyl ring and dihedral angles of 74.51 (10) and 56.38 (10)° with the planes of the benzene rings. In the crystal, pairs of N—H⋯N hydrogen bonds link molecules into inversion dimers featuring R22(8) graph-set motifs.
CCDC reference: 987804
Related literature
For background information and applications of oxadiazole derivatives, see: Schnurch et al. (2006); Crabtree (2005); Venkatakrishnan et al. (2000); Brown et al. (1992). For biological activity of oxadiazole derivatives, see: Omar et al. (1996); Talawar et al. (1996); Hamad et al. (1996); Tully et al. (1991); Barry et al. (1991); Ladduwahetty et al. (1996); Borg et al. (1999). For standard bond lengths, see: Allen et al. (1987). For a related structure, see: Shang et al. (2005).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON.
Supporting information
CCDC reference: 987804
10.1107/S1600536814003821/lh5692sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814003821/lh5692Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814003821/lh5692Isup3.cml
To a suspension of 2-[(2-(methoxyimino)-2-{2-[(2-methylphenoxy)methyl]phenyl}acetyl]-*N* -phenylhydrazinecarbothioamide (2.240 g, 5 mmol) in ethanol, potassium hydroxide solution (4 N, 30 ml) was added with cooling and shaking. A solution of 10% iodine in potassium iodide was added drop wise with stirring till the color of iodine persisted. The mixture was refluxed on a water bath for 4 h, and then left to cool. The separated solid was filtered off washed with water, by the process of slow evaporation recrystallized it from methanol.
H6' attached to N6 was located in a difference Fourier map and refined isotropically. The remaining H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.97 Å; and with Uiso(H) = 1.2Ueq(C), except for the methyl groups where Uiso(H) = 1.5Ueq(C),.
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).C24H22N4O3 | Z = 2 |
Mr = 414.46 | F(000) = 436 |
Triclinic, P1 | Dx = 1.276 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.0629 (4) Å | Cell parameters from 2043 reflections |
b = 12.5553 (9) Å | θ = 3.9–25.8° |
c = 13.3705 (11) Å | µ = 0.09 mm−1 |
α = 68.321 (7)° | T = 293 K |
β = 83.678 (6)° | Block, colourless |
γ = 78.567 (6)° | 0.30 × 0.20 × 0.20 mm |
V = 1079.04 (13) Å3 |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 4233 independent reflections |
Radiation source: fine-focus sealed tube | 2679 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 16.1049 pixels mm-1 | θmax = 26.0°, θmin = 3.5° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | k = −15→13 |
Tmin = 0.874, Tmax = 1.000 | l = −16→13 |
7584 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0476P)2] where P = (Fo2 + 2Fc2)/3 |
4233 reflections | (Δ/σ)max = 0.001 |
286 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C24H22N4O3 | γ = 78.567 (6)° |
Mr = 414.46 | V = 1079.04 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.0629 (4) Å | Mo Kα radiation |
b = 12.5553 (9) Å | µ = 0.09 mm−1 |
c = 13.3705 (11) Å | T = 293 K |
α = 68.321 (7)° | 0.30 × 0.20 × 0.20 mm |
β = 83.678 (6)° |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 4233 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | 2679 reflections with I > 2σ(I) |
Tmin = 0.874, Tmax = 1.000 | Rint = 0.023 |
7584 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.19 e Å−3 |
4233 reflections | Δρmin = −0.15 e Å−3 |
286 parameters |
Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 | 0.59108 (16) | 0.51331 (10) | 0.15728 (10) | 0.0477 (3) | |
O2 | 0.09810 (18) | 0.40040 (11) | 0.31402 (11) | 0.0599 (4) | |
N5 | 0.2555 (2) | 0.44773 (13) | 0.25488 (13) | 0.0503 (4) | |
O3 | 0.57360 (17) | 0.21849 (12) | 0.42203 (11) | 0.0591 (4) | |
N3 | 0.7893 (2) | 0.43994 (14) | 0.04992 (13) | 0.0505 (4) | |
C1 | 0.3357 (2) | 0.25405 (15) | 0.23721 (14) | 0.0408 (4) | |
C2 | 0.4559 (3) | 0.15355 (15) | 0.29884 (15) | 0.0443 (5) | |
C17 | 0.5374 (2) | 0.41397 (15) | 0.15669 (15) | 0.0428 (4) | |
N4 | 0.6492 (2) | 0.36807 (13) | 0.09560 (13) | 0.0503 (4) | |
C7 | 0.6318 (3) | 0.15775 (16) | 0.34995 (16) | 0.0513 (5) | |
H7A | 0.6962 | 0.0794 | 0.3887 | 0.062* | |
H7B | 0.7216 | 0.1971 | 0.2949 | 0.062* | |
N6 | 0.8571 (2) | 0.60402 (15) | 0.07479 (14) | 0.0549 (5) | |
C16 | 0.3681 (2) | 0.37311 (15) | 0.22091 (14) | 0.0420 (4) | |
C18 | 0.7501 (3) | 0.52194 (16) | 0.09016 (15) | 0.0448 (5) | |
C8 | 0.7125 (3) | 0.22372 (16) | 0.48381 (16) | 0.0460 (5) | |
C9 | 0.9052 (3) | 0.17465 (16) | 0.47816 (16) | 0.0514 (5) | |
H9 | 0.9485 | 0.1368 | 0.4297 | 0.062* | |
C10 | 1.0330 (3) | 0.18281 (17) | 0.54587 (18) | 0.0599 (6) | |
H10 | 1.1631 | 0.1512 | 0.5419 | 0.072* | |
C15 | −0.0188 (3) | 0.48144 (17) | 0.35618 (17) | 0.0598 (5) | |
H15A | 0.0509 | 0.4915 | 0.4089 | 0.090* | |
H15B | −0.1353 | 0.4527 | 0.3893 | 0.090* | |
H15C | −0.0510 | 0.5548 | 0.2988 | 0.090* | |
C3 | 0.4104 (3) | 0.04676 (16) | 0.31252 (17) | 0.0576 (6) | |
H3 | 0.4885 | −0.0206 | 0.3542 | 0.069* | |
C6 | 0.1759 (3) | 0.24319 (18) | 0.19236 (16) | 0.0525 (5) | |
H6 | 0.0941 | 0.3098 | 0.1525 | 0.063* | |
C13 | 0.6458 (3) | 0.28167 (17) | 0.55509 (17) | 0.0540 (5) | |
C11 | 0.9692 (3) | 0.23681 (19) | 0.61822 (18) | 0.0621 (6) | |
H11 | 1.0549 | 0.2403 | 0.6646 | 0.074* | |
C12 | 0.7771 (3) | 0.28617 (18) | 0.62222 (17) | 0.0607 (6) | |
H12 | 0.7349 | 0.3234 | 0.6713 | 0.073* | |
C19 | 0.8052 (3) | 0.71032 (17) | 0.09168 (16) | 0.0536 (5) | |
C5 | 0.1362 (3) | 0.1356 (2) | 0.20575 (18) | 0.0628 (6) | |
H5 | 0.0302 | 0.1298 | 0.1737 | 0.075* | |
C4 | 0.2533 (3) | 0.0375 (2) | 0.26631 (19) | 0.0650 (6) | |
H4 | 0.2266 | −0.0354 | 0.2762 | 0.078* | |
C24 | 0.9531 (4) | 0.7683 (2) | 0.08959 (18) | 0.0709 (6) | |
H24 | 1.0806 | 0.7354 | 0.0798 | 0.085* | |
C22 | 0.7283 (6) | 0.9234 (2) | 0.1171 (2) | 0.1028 (10) | |
H22 | 0.7021 | 0.9951 | 0.1258 | 0.123* | |
C23 | 0.9130 (5) | 0.8743 (2) | 0.1019 (2) | 0.0896 (8) | |
H23 | 1.0137 | 0.9130 | 0.0997 | 0.108* | |
C20 | 0.6179 (3) | 0.7598 (2) | 0.1058 (2) | 0.0837 (8) | |
H20 | 0.5165 | 0.7223 | 0.1062 | 0.100* | |
C14 | 0.4381 (3) | 0.3382 (2) | 0.5583 (2) | 0.0883 (8) | |
H14A | 0.4059 | 0.3956 | 0.4888 | 0.133* | |
H14B | 0.4189 | 0.3748 | 0.6111 | 0.133* | |
H14C | 0.3567 | 0.2802 | 0.5771 | 0.133* | |
C21 | 0.5811 (5) | 0.8661 (2) | 0.1194 (3) | 0.1116 (10) | |
H21 | 0.4543 | 0.8992 | 0.1304 | 0.134* | |
H6' | 0.975 (3) | 0.5895 (19) | 0.039 (2) | 0.088 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0448 (7) | 0.0463 (7) | 0.0474 (8) | −0.0087 (6) | 0.0157 (6) | −0.0156 (6) |
O2 | 0.0570 (8) | 0.0457 (8) | 0.0728 (10) | −0.0148 (7) | 0.0342 (7) | −0.0234 (7) |
N5 | 0.0458 (9) | 0.0449 (9) | 0.0513 (11) | −0.0104 (8) | 0.0191 (7) | −0.0114 (8) |
O3 | 0.0436 (8) | 0.0714 (9) | 0.0732 (11) | −0.0007 (7) | −0.0062 (7) | −0.0419 (8) |
N3 | 0.0400 (9) | 0.0536 (10) | 0.0539 (11) | −0.0067 (8) | 0.0127 (7) | −0.0193 (9) |
C1 | 0.0410 (10) | 0.0443 (10) | 0.0348 (11) | −0.0065 (8) | 0.0075 (8) | −0.0144 (9) |
C2 | 0.0458 (11) | 0.0436 (11) | 0.0424 (11) | −0.0060 (9) | 0.0030 (8) | −0.0162 (9) |
C17 | 0.0406 (10) | 0.0390 (10) | 0.0426 (12) | −0.0018 (8) | 0.0049 (8) | −0.0117 (9) |
N4 | 0.0422 (9) | 0.0528 (10) | 0.0534 (11) | −0.0075 (8) | 0.0116 (7) | −0.0200 (8) |
C7 | 0.0509 (12) | 0.0461 (11) | 0.0528 (13) | 0.0024 (9) | −0.0045 (9) | −0.0178 (10) |
N6 | 0.0481 (10) | 0.0530 (10) | 0.0604 (12) | −0.0149 (9) | 0.0221 (8) | −0.0203 (9) |
C16 | 0.0389 (10) | 0.0398 (10) | 0.0396 (11) | −0.0010 (8) | 0.0043 (8) | −0.0097 (9) |
C18 | 0.0379 (10) | 0.0484 (11) | 0.0395 (12) | −0.0031 (9) | 0.0089 (8) | −0.0110 (9) |
C8 | 0.0406 (11) | 0.0459 (11) | 0.0514 (13) | −0.0130 (9) | −0.0007 (9) | −0.0147 (9) |
C9 | 0.0472 (11) | 0.0489 (11) | 0.0564 (13) | −0.0068 (9) | −0.0030 (9) | −0.0175 (10) |
C10 | 0.0468 (12) | 0.0605 (13) | 0.0670 (16) | −0.0124 (10) | −0.0052 (11) | −0.0140 (12) |
C15 | 0.0588 (13) | 0.0536 (12) | 0.0630 (14) | −0.0063 (10) | 0.0255 (10) | −0.0256 (11) |
C3 | 0.0673 (14) | 0.0433 (11) | 0.0595 (14) | −0.0084 (10) | 0.0009 (11) | −0.0169 (10) |
C6 | 0.0474 (11) | 0.0636 (13) | 0.0448 (12) | −0.0046 (10) | 0.0010 (9) | −0.0205 (10) |
C13 | 0.0448 (11) | 0.0598 (12) | 0.0638 (14) | −0.0206 (10) | 0.0104 (10) | −0.0271 (11) |
C11 | 0.0621 (14) | 0.0693 (14) | 0.0570 (15) | −0.0264 (12) | −0.0048 (11) | −0.0167 (12) |
C12 | 0.0643 (14) | 0.0704 (14) | 0.0591 (15) | −0.0340 (12) | 0.0134 (11) | −0.0297 (12) |
C19 | 0.0650 (13) | 0.0486 (12) | 0.0401 (12) | −0.0123 (11) | 0.0133 (9) | −0.0105 (9) |
C5 | 0.0560 (13) | 0.0876 (17) | 0.0600 (15) | −0.0243 (13) | 0.0056 (11) | −0.0401 (13) |
C4 | 0.0752 (15) | 0.0620 (14) | 0.0699 (16) | −0.0254 (13) | 0.0125 (12) | −0.0346 (13) |
C24 | 0.0824 (16) | 0.0648 (15) | 0.0629 (16) | −0.0224 (13) | 0.0050 (12) | −0.0170 (12) |
C22 | 0.157 (3) | 0.0627 (17) | 0.089 (2) | −0.027 (2) | 0.025 (2) | −0.0315 (16) |
C23 | 0.130 (3) | 0.0741 (18) | 0.0700 (19) | −0.0429 (18) | 0.0010 (17) | −0.0207 (15) |
C20 | 0.0751 (17) | 0.0590 (15) | 0.112 (2) | −0.0109 (13) | 0.0269 (14) | −0.0335 (15) |
C14 | 0.0543 (14) | 0.114 (2) | 0.129 (2) | −0.0165 (14) | 0.0132 (14) | −0.0842 (19) |
C21 | 0.113 (2) | 0.0676 (18) | 0.140 (3) | −0.0059 (18) | 0.0436 (19) | −0.0384 (19) |
O1—C18 | 1.354 (2) | C15—H15B | 0.9600 |
O1—C17 | 1.377 (2) | C15—H15C | 0.9600 |
O2—N5 | 1.3912 (18) | C3—C4 | 1.372 (3) |
O2—C15 | 1.422 (2) | C3—H3 | 0.9300 |
N5—C16 | 1.287 (2) | C6—C5 | 1.377 (3) |
O3—C8 | 1.3759 (19) | C6—H6 | 0.9300 |
O3—C7 | 1.418 (2) | C13—C12 | 1.382 (3) |
N3—C18 | 1.300 (2) | C13—C14 | 1.501 (3) |
N3—N4 | 1.407 (2) | C11—C12 | 1.380 (3) |
C1—C6 | 1.386 (2) | C11—H11 | 0.9300 |
C1—C2 | 1.397 (2) | C12—H12 | 0.9300 |
C1—C16 | 1.489 (2) | C19—C20 | 1.370 (3) |
C2—C3 | 1.382 (2) | C19—C24 | 1.380 (3) |
C2—C7 | 1.501 (2) | C5—C4 | 1.365 (3) |
C17—N4 | 1.284 (2) | C5—H5 | 0.9300 |
C17—C16 | 1.456 (2) | C4—H4 | 0.9300 |
C7—H7A | 0.9700 | C24—C23 | 1.371 (3) |
C7—H7B | 0.9700 | C24—H24 | 0.9300 |
N6—C18 | 1.339 (2) | C22—C23 | 1.356 (4) |
N6—C19 | 1.406 (2) | C22—C21 | 1.368 (4) |
N6—H6' | 0.93 (2) | C22—H22 | 0.9300 |
C8—C9 | 1.385 (2) | C23—H23 | 0.9300 |
C8—C13 | 1.392 (3) | C20—C21 | 1.383 (3) |
C9—C10 | 1.389 (2) | C20—H20 | 0.9300 |
C9—H9 | 0.9300 | C14—H14A | 0.9600 |
C10—C11 | 1.366 (3) | C14—H14B | 0.9600 |
C10—H10 | 0.9300 | C14—H14C | 0.9600 |
C15—H15A | 0.9600 | C21—H21 | 0.9300 |
C18—O1—C17 | 102.10 (15) | C4—C3—C2 | 121.79 (18) |
N5—O2—C15 | 109.64 (13) | C4—C3—H3 | 119.1 |
C16—N5—O2 | 110.37 (14) | C2—C3—H3 | 119.1 |
C8—O3—C7 | 117.77 (14) | C5—C6—C1 | 121.23 (18) |
C18—N3—N4 | 105.98 (15) | C5—C6—H6 | 119.4 |
C6—C1—C2 | 119.05 (16) | C1—C6—H6 | 119.4 |
C6—C1—C16 | 118.34 (15) | C12—C13—C8 | 117.91 (18) |
C2—C1—C16 | 122.56 (14) | C12—C13—C14 | 121.1 (2) |
C3—C2—C1 | 118.43 (16) | C8—C13—C14 | 120.98 (17) |
C3—C2—C7 | 119.19 (16) | C10—C11—C12 | 119.67 (18) |
C1—C2—C7 | 122.38 (16) | C10—C11—H11 | 120.2 |
N4—C17—O1 | 112.81 (16) | C12—C11—H11 | 120.2 |
N4—C17—C16 | 127.54 (17) | C11—C12—C13 | 121.6 (2) |
O1—C17—C16 | 119.65 (16) | C11—C12—H12 | 119.2 |
C17—N4—N3 | 106.21 (14) | C13—C12—H12 | 119.2 |
O3—C7—C2 | 108.75 (15) | C20—C19—C24 | 119.4 (2) |
O3—C7—H7A | 109.9 | C20—C19—N6 | 123.6 (2) |
C2—C7—H7A | 109.9 | C24—C19—N6 | 116.96 (19) |
O3—C7—H7B | 109.9 | C4—C5—C6 | 119.65 (17) |
C2—C7—H7B | 109.9 | C4—C5—H5 | 120.2 |
H7A—C7—H7B | 108.3 | C6—C5—H5 | 120.2 |
C18—N6—C19 | 129.13 (18) | C5—C4—C3 | 119.83 (19) |
C18—N6—H6' | 111.4 (14) | C5—C4—H4 | 120.1 |
C19—N6—H6' | 118.8 (14) | C3—C4—H4 | 120.1 |
N5—C16—C17 | 115.10 (16) | C23—C24—C19 | 120.3 (2) |
N5—C16—C1 | 126.20 (17) | C23—C24—H24 | 119.9 |
C17—C16—C1 | 118.63 (16) | C19—C24—H24 | 119.9 |
N3—C18—N6 | 125.74 (18) | C23—C22—C21 | 119.2 (3) |
N3—C18—O1 | 112.89 (17) | C23—C22—H22 | 120.4 |
N6—C18—O1 | 121.25 (18) | C21—C22—H22 | 120.4 |
O3—C8—C9 | 123.67 (17) | C22—C23—C24 | 120.8 (3) |
O3—C8—C13 | 115.14 (16) | C22—C23—H23 | 119.6 |
C9—C8—C13 | 121.19 (17) | C24—C23—H23 | 119.6 |
C8—C9—C10 | 119.03 (19) | C19—C20—C21 | 119.3 (3) |
C8—C9—H9 | 120.5 | C19—C20—H20 | 120.3 |
C10—C9—H9 | 120.5 | C21—C20—H20 | 120.3 |
C11—C10—C9 | 120.60 (19) | C13—C14—H14A | 109.5 |
C11—C10—H10 | 119.7 | C13—C14—H14B | 109.5 |
C9—C10—H10 | 119.7 | H14A—C14—H14B | 109.5 |
O2—C15—H15A | 109.5 | C13—C14—H14C | 109.5 |
O2—C15—H15B | 109.5 | H14A—C14—H14C | 109.5 |
H15A—C15—H15B | 109.5 | H14B—C14—H14C | 109.5 |
O2—C15—H15C | 109.5 | C22—C21—C20 | 121.1 (3) |
H15A—C15—H15C | 109.5 | C22—C21—H21 | 119.5 |
H15B—C15—H15C | 109.5 | C20—C21—H21 | 119.5 |
C15—O2—N5—C16 | 176.64 (15) | C7—O3—C8—C13 | −178.30 (18) |
C6—C1—C2—C3 | 0.1 (3) | O3—C8—C9—C10 | −178.63 (18) |
C16—C1—C2—C3 | 177.78 (18) | C13—C8—C9—C10 | 0.6 (3) |
C6—C1—C2—C7 | 179.86 (17) | C8—C9—C10—C11 | 1.0 (3) |
C16—C1—C2—C7 | −2.4 (3) | C1—C2—C3—C4 | 0.8 (3) |
C18—O1—C17—N4 | −0.61 (19) | C7—C2—C3—C4 | −178.94 (19) |
C18—O1—C17—C16 | 179.83 (15) | C2—C1—C6—C5 | −1.3 (3) |
O1—C17—N4—N3 | −0.39 (19) | C16—C1—C6—C5 | −179.06 (18) |
C16—C17—N4—N3 | 179.14 (16) | O3—C8—C13—C12 | 177.67 (17) |
C18—N3—N4—C17 | 1.28 (19) | C9—C8—C13—C12 | −1.7 (3) |
C8—O3—C7—C2 | 174.85 (15) | O3—C8—C13—C14 | −2.7 (3) |
C3—C2—C7—O3 | −120.2 (2) | C9—C8—C13—C14 | 177.93 (19) |
C1—C2—C7—O3 | 60.0 (2) | C9—C10—C11—C12 | −1.6 (3) |
O2—N5—C16—C17 | 179.34 (14) | C10—C11—C12—C13 | 0.5 (3) |
O2—N5—C16—C1 | 2.2 (2) | C8—C13—C12—C11 | 1.1 (3) |
N4—C17—C16—N5 | −164.43 (18) | C14—C13—C12—C11 | −178.5 (2) |
O1—C17—C16—N5 | 15.1 (2) | C18—N6—C19—C20 | −14.8 (3) |
N4—C17—C16—C1 | 12.9 (3) | C18—N6—C19—C24 | 167.7 (2) |
O1—C17—C16—C1 | −167.60 (14) | C1—C6—C5—C4 | 1.5 (3) |
C6—C1—C16—N5 | 63.0 (3) | C6—C5—C4—C3 | −0.6 (3) |
C2—C1—C16—N5 | −114.7 (2) | C2—C3—C4—C5 | −0.6 (3) |
C6—C1—C16—C17 | −114.00 (19) | C20—C19—C24—C23 | 0.2 (3) |
C2—C1—C16—C17 | 68.3 (2) | N6—C19—C24—C23 | 177.8 (2) |
N4—N3—C18—N6 | 174.36 (17) | C21—C22—C23—C24 | −0.4 (4) |
N4—N3—C18—O1 | −1.76 (19) | C19—C24—C23—C22 | 0.5 (4) |
C19—N6—C18—N3 | 162.55 (19) | C24—C19—C20—C21 | −1.0 (4) |
C19—N6—C18—O1 | −21.6 (3) | N6—C19—C20—C21 | −178.5 (2) |
C17—O1—C18—N3 | 1.49 (19) | C23—C22—C21—C20 | −0.5 (5) |
C17—O1—C18—N6 | −174.82 (16) | C19—C20—C21—C22 | 1.2 (4) |
C7—O3—C8—C9 | 1.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6′···N3i | 0.93 (2) | 1.99 (2) | 2.922 (2) | 174 |
Symmetry code: (i) −x+2, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6'···N3i | 0.93 (2) | 1.99 (2) | 2.922 (2) | 174 |
Symmetry code: (i) −x+2, −y+1, −z. |
Acknowledgements
RK acknowledges the Department of Science & Technology for the purchase of a single-crystal X-ray diffractometer sanctioned as a National Facility under Project No. SR/S2/CMP-47/2003.
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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.
Derivatives of oxadiazole systems are a growing research interest, as they are precursors to functional N-heterocyclic compounds, as well as being used in pharmaceuticals as metabolically stable surrogates and photographically active systems (Schnurch et al., 2006; Crabtree, 2005; Venkatakrishnan, et al., 2000). Symmetrical and unsymmetrical 1,3,4-oxadiazoles have been reported to be versatile compounds displaying a variety of biological effects, which include anti-inflammatory (Omar et al., 1996), antifungal (Talawar et al., 1996) and antimicrobial (Hamad et al., 1996) activities. They have been utilized as bioisosteres of the carboxamide moiety in benzodiazepine receptor agonists, muscarinic receptor agonists, NK1 receptor antagonists, and Phe–Gly peptidomimetics (Tully et al., 1991; Barry et al., 1991; Ladduwahetty et al., 1996; Borg et al., 1999). Moreover, oxadiazole derivatives have been widely used as electron-conducting and hole-blocking materials in moleculebased as well as polymeric light-emitting devices (LEDs) due to the electron-deficient and favourable electron-transport properties of the oxadiazole rings (Brown et al., 1992).
In the molecule of the title compound, Fig.1, bond lengths are in normal ranges (Allen et al., 1987) and are comparable with a related structure (Shang et al., 2005). The oxadiazole ring (O1/N3/N4/C17/C18) forms a dihedral angle of 32.41 (12)° with the phenyl ring (C19-C24) and dihedral angles 74.51 (10) and 56.38 (10)° with the benzene rings (C1-C6 and C8-C13, respectfully). In the crystal, pairs of N—H···N hydrogen bonds form inversion dimers (Fig. 2).