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organic compounds
4-[5-(4-Benzoyloxyphenyl)-1,2,4-oxadiazol-3-yl]phenyl benzoate
aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore, 570 006, India, and bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore, 570 006, India
*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in
In the title compound, C28H18N2O5, the dihedral angle between the terminal benzoate rings is 20.67 (12)°. The central oxadiazole ring is almost coplanar with its two benzene ring substituents, making dihedral angles of 4.80 (16) and 5.82 (16)°. In the crystal, pairs of C—H⋯O hydrogen bonds form inversion dimers with R22(40) ring motifs. The structure also features C—H⋯O, C—H⋯π and π–π interactions [centroid–centroid separation = 3.695 (4) Å].
Related literature
For the use of oxadiazole derivatives as antimicrobial agents, see: Dhol et al. (2005) and for a related structure, see: Emmerling et al. (2006
). For hydrogen-bond motifs, see: Bernstein et al. (1995
).
Experimental
Crystal data
|
Data collection
|
Refinement
|
|
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); 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: Mercury (Macrae et al., 2008
); software used to prepare material for publication: SHELXL97 and Mercury.
Supporting information
10.1107/S1600536813006922/sj5303sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813006922/sj5303Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813006922/sj5303Isup3.cml
4-[(E)-(hydroxyimino)methyl] phenyl benzoate (4.8 mmole) was dissolved in chloroform, N-chlorosuccinimide (5.2 mmole) was added followed by slow addition of sodium carbonate (8.8 mmole) at room temperature. Then, the resulting reaction mixture was stirred for up to 18 h. After completion of reaction (monitored by TLC), the reaction mixture was diluted with water (50 ml). The aqueous layer was extracted with ethyl acetate (3*20 ml), the combined ethyl acetate layer was washed with brine solution (2*25 ml). Then, the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude product, which was further purified by
over silica gel (60–120 mesh) using hexane:ethyl acetate mixture in an 8:2 ratio as The pure compound was crystallized from ethyl acetate and hexane, to give white single crystals.1H NMR (DMSO-d6, 300 MHz): δ 7.33 (t, J=7.2 Hz, 2H), 7.13 (T, J=8.7 Hz, 4H), 7.02 (t, J=7.2 Hz, 2H), 6.75 (s, 2H), 4.51 (d, J=1.8 Hz, 2H), 3.08 (s, 1H).
Mass: Calc. 231.3 found: 232 (M+1). Melting point (°C): 90 (Uncorrected)
All hydrogen atoms were located geometrically with C—H = 0.93–0.97) Å and allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(aromatic C) or 1.5Uiso(methyl C).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and Mercury (Macrae et al., 2008).C28H18N2O5 | F(000) = 960 |
Mr = 462.44 | Dx = 1.344 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4513 reflections |
a = 21.069 (18) Å | θ = 2.0–26.0° |
b = 6.063 (5) Å | µ = 0.09 mm−1 |
c = 18.727 (16) Å | T = 300 K |
β = 107.159 (13)° | Needle, white |
V = 2286 (3) Å3 | 0.23 × 0.23 × 0.22 mm |
Z = 4 |
Oxford Diffraction Xcalibur Eos diffractometer | 2518 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.060 |
Graphite monochromator | θmax = 26.0°, θmin = 2.0° |
Detector resolution: 16.0839 pixels mm-1 | h = −26→26 |
ω scans | k = −7→7 |
21331 measured reflections | l = −23→23 |
4513 independent 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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.191 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0786P)2 + 0.5948P] where P = (Fo2 + 2Fc2)/3 |
4513 reflections | (Δ/σ)max < 0.001 |
316 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C28H18N2O5 | V = 2286 (3) Å3 |
Mr = 462.44 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 21.069 (18) Å | µ = 0.09 mm−1 |
b = 6.063 (5) Å | T = 300 K |
c = 18.727 (16) Å | 0.23 × 0.23 × 0.22 mm |
β = 107.159 (13)° |
Oxford Diffraction Xcalibur Eos diffractometer | 2518 reflections with I > 2σ(I) |
21331 measured reflections | Rint = 0.060 |
4513 independent reflections |
R[F2 > 2σ(F2)] = 0.068 | 0 restraints |
wR(F2) = 0.191 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.38 e Å−3 |
4513 reflections | Δρmin = −0.22 e Å−3 |
316 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 | 0.53828 (13) | 1.1931 (4) | 0.31832 (14) | 0.1027 (11) | |
O2 | 0.76931 (12) | 0.6953 (4) | 0.21732 (12) | 0.0864 (9) | |
O3 | 0.84189 (14) | 0.9715 (5) | 0.25694 (17) | 0.1262 (12) | |
O4 | 0.29559 (10) | 0.7471 (3) | 0.52085 (12) | 0.0762 (8) | |
O5 | 0.25276 (10) | 0.4910 (4) | 0.43300 (12) | 0.0811 (8) | |
N1 | 0.48512 (12) | 1.1945 (4) | 0.35022 (14) | 0.0723 (10) | |
N2 | 0.53434 (12) | 0.8645 (4) | 0.36922 (13) | 0.0652 (9) | |
C1 | 0.56466 (16) | 0.9925 (5) | 0.33120 (16) | 0.0686 (11) | |
C2 | 0.48632 (15) | 0.9947 (5) | 0.37851 (16) | 0.0662 (11) | |
C3 | 0.62017 (15) | 0.9293 (5) | 0.30344 (16) | 0.0671 (11) | |
C4 | 0.64460 (17) | 1.0655 (5) | 0.25813 (18) | 0.0801 (12) | |
C5 | 0.69506 (19) | 0.9989 (6) | 0.23065 (18) | 0.0837 (14) | |
C6 | 0.72168 (16) | 0.7925 (6) | 0.24910 (17) | 0.0753 (11) | |
C7 | 0.69841 (17) | 0.6508 (6) | 0.29357 (19) | 0.0867 (14) | |
C8 | 0.64812 (17) | 0.7210 (6) | 0.32118 (19) | 0.0828 (12) | |
C9 | 0.8266 (2) | 0.7982 (6) | 0.22570 (19) | 0.0887 (14) | |
C10 | 0.87083 (16) | 0.6675 (6) | 0.19119 (17) | 0.0716 (11) | |
C11 | 0.9304 (2) | 0.7655 (7) | 0.1915 (2) | 0.1027 (17) | |
C12 | 0.9727 (2) | 0.6540 (10) | 0.1601 (3) | 0.135 (3) | |
C13 | 0.9549 (3) | 0.4485 (10) | 0.1288 (3) | 0.133 (3) | |
C14 | 0.8977 (2) | 0.3540 (7) | 0.1302 (2) | 0.1070 (17) | |
C15 | 0.85597 (18) | 0.4614 (6) | 0.16063 (19) | 0.0853 (12) | |
C16 | 0.43672 (14) | 0.9309 (5) | 0.41587 (16) | 0.0626 (10) | |
C17 | 0.38540 (16) | 1.0725 (5) | 0.41790 (18) | 0.0765 (11) | |
C18 | 0.33900 (16) | 1.0085 (5) | 0.45203 (18) | 0.0768 (12) | |
C19 | 0.34337 (14) | 0.8044 (5) | 0.48421 (17) | 0.0669 (11) | |
C20 | 0.39386 (14) | 0.6606 (5) | 0.48425 (17) | 0.0707 (11) | |
C21 | 0.44033 (14) | 0.7249 (5) | 0.44904 (18) | 0.0712 (11) | |
C22 | 0.25088 (13) | 0.5876 (5) | 0.48832 (17) | 0.0610 (10) | |
C23 | 0.20080 (14) | 0.5533 (5) | 0.52860 (15) | 0.0637 (10) | |
C24 | 0.18931 (16) | 0.7044 (6) | 0.57868 (19) | 0.0821 (12) | |
C25 | 0.14077 (19) | 0.6633 (7) | 0.6137 (2) | 0.1033 (17) | |
C26 | 0.1046 (2) | 0.4723 (8) | 0.5987 (2) | 0.1142 (19) | |
C27 | 0.1155 (2) | 0.3225 (7) | 0.5490 (2) | 0.1099 (17) | |
C28 | 0.16333 (17) | 0.3616 (6) | 0.51374 (19) | 0.0847 (12) | |
H4 | 0.62630 | 1.20520 | 0.24610 | 0.0960* | |
H5 | 0.71090 | 1.09150 | 0.20020 | 0.1010* | |
H7 | 0.71640 | 0.51040 | 0.30460 | 0.1040* | |
H8 | 0.63270 | 0.62840 | 0.35200 | 0.0990* | |
H11 | 0.94170 | 0.90420 | 0.21260 | 0.1230* | |
H12 | 1.01290 | 0.71690 | 0.15990 | 0.1620* | |
H13 | 0.98290 | 0.37480 | 0.10660 | 0.1590* | |
H14 | 0.88690 | 0.21390 | 0.11010 | 0.1280* | |
H15 | 0.81630 | 0.39450 | 0.16090 | 0.1020* | |
H17 | 0.38250 | 1.21130 | 0.39600 | 0.0920* | |
H18 | 0.30470 | 1.10360 | 0.45330 | 0.0920* | |
H20 | 0.39680 | 0.52360 | 0.50730 | 0.0850* | |
H21 | 0.47430 | 0.62860 | 0.44770 | 0.0860* | |
H24 | 0.21410 | 0.83370 | 0.58900 | 0.0980* | |
H25 | 0.13290 | 0.76530 | 0.64710 | 0.1240* | |
H26 | 0.07250 | 0.44430 | 0.62250 | 0.1370* | |
H27 | 0.09040 | 0.19370 | 0.53890 | 0.1320* | |
H28 | 0.17050 | 0.25920 | 0.48000 | 0.1010* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.124 (2) | 0.0824 (18) | 0.0989 (18) | −0.0007 (15) | 0.0286 (16) | 0.0218 (14) |
O2 | 0.0992 (16) | 0.0847 (16) | 0.0788 (15) | −0.0287 (13) | 0.0317 (13) | −0.0061 (12) |
O3 | 0.134 (2) | 0.108 (2) | 0.140 (2) | −0.0487 (18) | 0.0455 (19) | −0.0497 (19) |
O4 | 0.0674 (13) | 0.0807 (14) | 0.0840 (15) | −0.0038 (11) | 0.0280 (12) | −0.0221 (12) |
O5 | 0.0824 (14) | 0.0908 (15) | 0.0799 (14) | −0.0105 (12) | 0.0390 (12) | −0.0273 (13) |
N1 | 0.0765 (17) | 0.0628 (16) | 0.0831 (17) | 0.0104 (13) | 0.0320 (14) | 0.0243 (13) |
N2 | 0.0726 (16) | 0.0600 (15) | 0.0624 (15) | −0.0061 (13) | 0.0191 (13) | 0.0076 (12) |
C1 | 0.080 (2) | 0.061 (2) | 0.0573 (17) | −0.0043 (17) | 0.0088 (16) | 0.0033 (15) |
C2 | 0.0684 (19) | 0.0625 (19) | 0.0574 (17) | 0.0006 (16) | 0.0025 (15) | 0.0046 (15) |
C3 | 0.081 (2) | 0.062 (2) | 0.0541 (16) | −0.0140 (16) | 0.0136 (15) | 0.0024 (14) |
C4 | 0.103 (2) | 0.063 (2) | 0.076 (2) | −0.0104 (18) | 0.029 (2) | 0.0037 (17) |
C5 | 0.117 (3) | 0.063 (2) | 0.079 (2) | −0.017 (2) | 0.041 (2) | 0.0073 (17) |
C6 | 0.088 (2) | 0.080 (2) | 0.0610 (19) | −0.0149 (18) | 0.0268 (17) | −0.0039 (17) |
C7 | 0.099 (3) | 0.078 (2) | 0.092 (2) | 0.0024 (19) | 0.042 (2) | 0.0207 (19) |
C8 | 0.094 (2) | 0.083 (2) | 0.079 (2) | −0.002 (2) | 0.0375 (19) | 0.0237 (18) |
C9 | 0.118 (3) | 0.070 (2) | 0.071 (2) | −0.036 (2) | 0.017 (2) | −0.0065 (18) |
C10 | 0.077 (2) | 0.073 (2) | 0.0596 (18) | −0.0037 (17) | 0.0122 (16) | 0.0088 (16) |
C11 | 0.086 (3) | 0.081 (3) | 0.126 (3) | −0.016 (2) | 0.008 (2) | 0.016 (2) |
C12 | 0.072 (3) | 0.136 (4) | 0.199 (6) | −0.002 (3) | 0.043 (3) | 0.057 (4) |
C13 | 0.103 (4) | 0.137 (5) | 0.164 (5) | 0.042 (3) | 0.049 (3) | 0.035 (4) |
C14 | 0.100 (3) | 0.102 (3) | 0.107 (3) | 0.014 (3) | 0.012 (3) | −0.005 (2) |
C15 | 0.083 (2) | 0.079 (2) | 0.085 (2) | −0.013 (2) | 0.0110 (19) | 0.003 (2) |
C16 | 0.0580 (16) | 0.0601 (18) | 0.0608 (17) | 0.0017 (14) | 0.0040 (14) | 0.0029 (14) |
C17 | 0.083 (2) | 0.0592 (19) | 0.079 (2) | 0.0108 (17) | 0.0112 (18) | 0.0068 (16) |
C18 | 0.073 (2) | 0.065 (2) | 0.087 (2) | 0.0168 (16) | 0.0153 (18) | −0.0068 (17) |
C19 | 0.0598 (18) | 0.063 (2) | 0.073 (2) | 0.0007 (15) | 0.0121 (15) | −0.0117 (16) |
C20 | 0.0617 (18) | 0.0625 (19) | 0.087 (2) | 0.0075 (15) | 0.0204 (17) | 0.0120 (16) |
C21 | 0.0599 (18) | 0.0613 (19) | 0.091 (2) | 0.0121 (14) | 0.0200 (17) | 0.0127 (16) |
C22 | 0.0583 (17) | 0.0588 (17) | 0.0639 (18) | 0.0085 (14) | 0.0151 (15) | −0.0079 (15) |
C23 | 0.0648 (18) | 0.0643 (19) | 0.0612 (17) | 0.0082 (15) | 0.0176 (15) | −0.0084 (15) |
C24 | 0.080 (2) | 0.085 (2) | 0.085 (2) | 0.0062 (18) | 0.0301 (19) | −0.0206 (19) |
C25 | 0.102 (3) | 0.120 (3) | 0.102 (3) | 0.004 (3) | 0.052 (2) | −0.040 (3) |
C26 | 0.117 (3) | 0.135 (4) | 0.115 (3) | −0.013 (3) | 0.072 (3) | −0.025 (3) |
C27 | 0.126 (3) | 0.108 (3) | 0.119 (3) | −0.032 (3) | 0.072 (3) | −0.025 (3) |
C28 | 0.102 (2) | 0.078 (2) | 0.087 (2) | −0.006 (2) | 0.048 (2) | −0.0178 (19) |
O1—N1 | 1.416 (4) | C18—C19 | 1.368 (4) |
O1—C1 | 1.329 (4) | C19—C20 | 1.375 (4) |
O2—C6 | 1.436 (4) | C20—C21 | 1.388 (5) |
O2—C9 | 1.326 (5) | C22—C23 | 1.482 (4) |
O3—C9 | 1.200 (5) | C23—C24 | 1.383 (5) |
O4—C19 | 1.419 (4) | C23—C28 | 1.386 (5) |
O4—C22 | 1.362 (4) | C24—C25 | 1.391 (5) |
O5—C22 | 1.201 (4) | C25—C26 | 1.369 (6) |
N1—C2 | 1.319 (4) | C26—C27 | 1.368 (6) |
N2—C1 | 1.336 (4) | C27—C28 | 1.379 (6) |
N2—C2 | 1.335 (4) | C4—H4 | 0.9300 |
C1—C3 | 1.464 (5) | C5—H5 | 0.9300 |
C2—C16 | 1.471 (5) | C7—H7 | 0.9300 |
C3—C4 | 1.387 (5) | C8—H8 | 0.9300 |
C3—C8 | 1.392 (5) | C11—H11 | 0.9300 |
C4—C5 | 1.372 (5) | C12—H12 | 0.9300 |
C5—C6 | 1.373 (5) | C13—H13 | 0.9300 |
C6—C7 | 1.383 (5) | C14—H14 | 0.9300 |
C7—C8 | 1.376 (5) | C15—H15 | 0.9300 |
C9—C10 | 1.506 (5) | C17—H17 | 0.9300 |
C10—C11 | 1.387 (6) | C18—H18 | 0.9300 |
C10—C15 | 1.372 (5) | C20—H20 | 0.9300 |
C11—C12 | 1.381 (7) | C21—H21 | 0.9300 |
C12—C13 | 1.381 (8) | C24—H24 | 0.9300 |
C13—C14 | 1.342 (8) | C25—H25 | 0.9300 |
C14—C15 | 1.348 (6) | C26—H26 | 0.9300 |
C16—C17 | 1.390 (5) | C27—H27 | 0.9300 |
C16—C21 | 1.387 (4) | C28—H28 | 0.9300 |
C17—C18 | 1.372 (5) | ||
N1—O1—C1 | 105.6 (2) | C22—C23—C24 | 123.1 (3) |
C6—O2—C9 | 118.8 (3) | C22—C23—C28 | 117.7 (3) |
C19—O4—C22 | 117.0 (2) | C24—C23—C28 | 119.2 (3) |
O1—N1—C2 | 103.9 (2) | C23—C24—C25 | 120.1 (3) |
C1—N2—C2 | 103.1 (3) | C24—C25—C26 | 119.8 (4) |
O1—C1—N2 | 112.8 (3) | C25—C26—C27 | 120.4 (4) |
O1—C1—C3 | 120.7 (3) | C26—C27—C28 | 120.3 (4) |
N2—C1—C3 | 126.5 (3) | C23—C28—C27 | 120.1 (3) |
N1—C2—N2 | 114.6 (3) | C3—C4—H4 | 119.00 |
N1—C2—C16 | 120.0 (3) | C5—C4—H4 | 119.00 |
N2—C2—C16 | 125.4 (3) | C4—C5—H5 | 121.00 |
C1—C3—C4 | 122.7 (3) | C6—C5—H5 | 121.00 |
C1—C3—C8 | 118.6 (3) | C6—C7—H7 | 121.00 |
C4—C3—C8 | 118.6 (3) | C8—C7—H7 | 121.00 |
C3—C4—C5 | 121.5 (3) | C3—C8—H8 | 120.00 |
C4—C5—C6 | 118.6 (3) | C7—C8—H8 | 120.00 |
O2—C6—C5 | 123.6 (3) | C10—C11—H11 | 120.00 |
O2—C6—C7 | 114.2 (3) | C12—C11—H11 | 120.00 |
C5—C6—C7 | 121.8 (3) | C11—C12—H12 | 120.00 |
C6—C7—C8 | 118.9 (3) | C13—C12—H12 | 120.00 |
C3—C8—C7 | 120.6 (3) | C12—C13—H13 | 120.00 |
O2—C9—O3 | 125.0 (4) | C14—C13—H13 | 120.00 |
O2—C9—C10 | 111.0 (3) | C13—C14—H14 | 120.00 |
O3—C9—C10 | 124.0 (4) | C15—C14—H14 | 120.00 |
C9—C10—C11 | 116.5 (3) | C10—C15—H15 | 119.00 |
C9—C10—C15 | 124.4 (3) | C14—C15—H15 | 119.00 |
C11—C10—C15 | 119.1 (3) | C16—C17—H17 | 120.00 |
C10—C11—C12 | 119.0 (4) | C18—C17—H17 | 120.00 |
C11—C12—C13 | 119.6 (5) | C17—C18—H18 | 120.00 |
C12—C13—C14 | 120.7 (5) | C19—C18—H18 | 120.00 |
C13—C14—C15 | 120.2 (4) | C19—C20—H20 | 121.00 |
C10—C15—C14 | 121.3 (4) | C21—C20—H20 | 121.00 |
C2—C16—C17 | 121.2 (3) | C16—C21—H21 | 120.00 |
C2—C16—C21 | 119.8 (3) | C20—C21—H21 | 120.00 |
C17—C16—C21 | 119.0 (3) | C23—C24—H24 | 120.00 |
C16—C17—C18 | 120.3 (3) | C25—C24—H24 | 120.00 |
C17—C18—C19 | 119.8 (3) | C24—C25—H25 | 120.00 |
O4—C19—C18 | 118.0 (3) | C26—C25—H25 | 120.00 |
O4—C19—C20 | 120.2 (3) | C25—C26—H26 | 120.00 |
C18—C19—C20 | 121.7 (3) | C27—C26—H26 | 120.00 |
C19—C20—C21 | 118.4 (3) | C26—C27—H27 | 120.00 |
C16—C21—C20 | 120.8 (3) | C28—C27—H27 | 120.00 |
O4—C22—O5 | 122.5 (3) | C23—C28—H28 | 120.00 |
O4—C22—C23 | 112.0 (2) | C27—C28—H28 | 120.00 |
O5—C22—C23 | 125.5 (3) | ||
C1—O1—N1—C2 | 0.2 (3) | O2—C9—C10—C11 | 175.5 (3) |
N1—O1—C1—N2 | −0.8 (3) | O2—C9—C10—C15 | −4.9 (5) |
N1—O1—C1—C3 | 178.0 (3) | O3—C9—C10—C11 | −5.0 (5) |
C9—O2—C6—C5 | 59.1 (4) | O3—C9—C10—C15 | 174.6 (4) |
C9—O2—C6—C7 | −128.3 (3) | C9—C10—C11—C12 | −179.5 (4) |
C6—O2—C9—O3 | −1.6 (5) | C15—C10—C11—C12 | 0.9 (6) |
C6—O2—C9—C10 | 177.9 (3) | C9—C10—C15—C14 | 179.6 (3) |
C22—O4—C19—C18 | 111.2 (3) | C11—C10—C15—C14 | −0.8 (5) |
C22—O4—C19—C20 | −71.4 (4) | C10—C11—C12—C13 | 0.3 (7) |
C19—O4—C22—O5 | 3.2 (4) | C11—C12—C13—C14 | −1.6 (8) |
C19—O4—C22—C23 | −176.0 (2) | C12—C13—C14—C15 | 1.7 (7) |
O1—N1—C2—C16 | −178.9 (3) | C13—C14—C15—C10 | −0.5 (6) |
O1—N1—C2—N2 | 0.5 (3) | C2—C16—C17—C18 | 179.0 (3) |
C2—N2—C1—C3 | −177.6 (3) | C21—C16—C17—C18 | −0.2 (5) |
C1—N2—C2—C16 | 178.4 (3) | C2—C16—C21—C20 | −179.6 (3) |
C2—N2—C1—O1 | 1.1 (3) | C17—C16—C21—C20 | −0.4 (5) |
C1—N2—C2—N1 | −1.0 (3) | C16—C17—C18—C19 | 0.0 (5) |
O1—C1—C3—C8 | 177.1 (3) | C17—C18—C19—O4 | 178.2 (3) |
N2—C1—C3—C4 | 173.5 (3) | C17—C18—C19—C20 | 0.8 (5) |
N2—C1—C3—C8 | −4.2 (5) | O4—C19—C20—C21 | −178.7 (3) |
O1—C1—C3—C4 | −5.1 (5) | C18—C19—C20—C21 | −1.5 (5) |
N1—C2—C16—C17 | 4.3 (4) | C19—C20—C21—C16 | 1.2 (5) |
N1—C2—C16—C21 | −176.5 (3) | O4—C22—C23—C24 | 17.3 (4) |
N2—C2—C16—C17 | −175.0 (3) | O4—C22—C23—C28 | −163.9 (3) |
N2—C2—C16—C21 | 4.1 (5) | O5—C22—C23—C24 | −161.9 (3) |
C1—C3—C4—C5 | −177.6 (3) | O5—C22—C23—C28 | 17.0 (5) |
C8—C3—C4—C5 | 0.2 (5) | C22—C23—C24—C25 | 179.0 (3) |
C1—C3—C8—C7 | 177.1 (3) | C28—C23—C24—C25 | 0.2 (5) |
C4—C3—C8—C7 | −0.8 (5) | C22—C23—C28—C27 | −179.3 (3) |
C3—C4—C5—C6 | −0.2 (5) | C24—C23—C28—C27 | −0.4 (5) |
C4—C5—C6—O2 | 172.9 (3) | C23—C24—C25—C26 | 0.3 (6) |
C4—C5—C6—C7 | 0.8 (5) | C24—C25—C26—C27 | −0.6 (6) |
O2—C6—C7—C8 | −174.1 (3) | C25—C26—C27—C28 | 0.4 (6) |
C5—C6—C7—C8 | −1.3 (5) | C26—C27—C28—C23 | 0.1 (6) |
C6—C7—C8—C3 | 1.3 (5) |
Cg3 is the centroid of the C10–C15 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···O5i | 0.93 | 2.57 | 3.407 (5) | 150 |
C25—H25···O3ii | 0.93 | 2.34 | 3.222 (6) | 158 |
C28—H28···Cg3iii | 0.93 | 2.96 | 3.678 (5) | 135 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C28H18N2O5 |
Mr | 462.44 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 300 |
a, b, c (Å) | 21.069 (18), 6.063 (5), 18.727 (16) |
β (°) | 107.159 (13) |
V (Å3) | 2286 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.23 × 0.23 × 0.22 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Eos diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21331, 4513, 2518 |
Rint | 0.060 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.191, 1.03 |
No. of reflections | 4513 |
No. of parameters | 316 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.22 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and Mercury (Macrae et al., 2008).
Cg3 is the centroid of the C10–C15 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···O5i | 0.9300 | 2.5700 | 3.407 (5) | 150.00 |
C25—H25···O3ii | 0.9300 | 2.3400 | 3.222 (6) | 158.00 |
C28—H28···Cg3iii | 0.9300 | 2.9600 | 3.678 (5) | 135.00 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, y−1/2, −z+1/2. |
Acknowledgements
MKS thanks theUGC–BRS and the UoM for the award of a fellowship, and MPS gratefully acknowledges financial support (grant F. No. 37–456/2009[SR]) from the UGC, India.
References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Dhol, S. R., Bhimani, A. S., Khunt, R. C. & Parik, A. R. (2005). Indian J. Heterocycl. Chem. 15, 63–64. CAS Google Scholar
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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.
Oxadiazole derivatives are known to act as antimicrobial agents (Dhol, et al., 2005). In the title oxadiazole derivative, C28H18N2O5, (Fig. 1), the geometry of the oxodiazole ring is comparable to that found in similar molecules (Emmerling et al., 2006). The dihedral angle between the two terminal benzoate rings is 20.67 (12)°. The central oxadiazole ring and its two benzene ring substituents are almost co-planar with the dihedral angles between the O1/C1/N1/C2/N2/ oxadiazole ring and the C3/C4/C5/C6/C7/C8 and C16/C17/C18/C19/C20/C21 benzene rings are 4.80 (16)° and 5.82 (16)° respectively.
C25–H25···O3 hydrogen bonds (Table 1) link adjacent molecules to form inversion dimers with R22(40) ring motifs (Bernstein et al., 1995). An additional C18–H18···O5 contact together with a C28—H28···Cg3 interaction (Table 1) and a Cg1···Cg2iv π···π contact with a centroid-centroid distance of 3.695 (4) Å further stabilise the packing. Cg1 and Cg2 are the centroids of the O1/N1/C1/C2/N2 and C3/C4/C5/C6/C7/C8 rings, respectively and iv = -x + 1, -y - 1/2, -z + 1.