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ISSN: 2056-9890

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

(Received 26 February 2013; accepted 12 March 2013; online 16 March 2013)

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 ππ inter­actions [centroid–centroid separation = 3.695 (4) Å].

Related literature

For the use of oxadiazole derivatives as anti­microbial agents, see: Dhol et al. (2005[Dhol, S. R., Bhimani, A. S., Khunt, R. C. & Parik, A. R. (2005). Indian J. Heterocycl. Chem. 15, 63-64.]) and for a related structure, see: Emmerling et al. (2006[Emmerling, F., Orgzall, I., Reck, G., Schulz, B. W., Stackhause, S. & Schulz, B. (2006). J. Mol. Struct. 800, 74-84.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C28H18N2O5

  • Mr = 462.44

  • Monoclinic, P 21 /c

  • a = 21.069 (18) Å

  • b = 6.063 (5) Å

  • c = 18.727 (16) Å

  • β = 107.159 (13)°

  • V = 2286 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 300 K

  • 0.23 × 0.23 × 0.22 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • 21331 measured reflections

  • 4513 independent reflections

  • 2518 reflections with I > 2σ(I)

  • Rint = 0.060

Refinement
  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.191

  • S = 1.03

  • 4513 reflections

  • 316 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C10–C15 ring.

D—H⋯A D—H H⋯A DA 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-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and Mercury.

Supporting information


Comment top

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.

Related literature top

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 top

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 column chromatography over silica gel (60–120 mesh) using hexane:ethyl acetate mixture in an 8:2 ratio as eluent. 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)

Refinement top

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).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. ORTEP diagram of the title molecule with 50% probability ellipsoids.
[Figure 2] Fig. 2. Packing diagram of molecule, viewed along the crystallographic b axis. Dotted lines represent intermolecular hydrogen bonds.
4-[5-(4-Benzoyloxyphenyl)-1,2,4-oxadiazol-3-yl]phenyl benzoate top
Crystal data top
C28H18N2O5F(000) = 960
Mr = 462.44Dx = 1.344 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4513 reflections
a = 21.069 (18) Åθ = 2.0–26.0°
b = 6.063 (5) ŵ = 0.09 mm1
c = 18.727 (16) ÅT = 300 K
β = 107.159 (13)°Needle, white
V = 2286 (3) Å30.23 × 0.23 × 0.22 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
2518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.060
Graphite monochromatorθmax = 26.0°, θmin = 2.0°
Detector resolution: 16.0839 pixels mm-1h = 2626
ω scansk = 77
21331 measured reflectionsl = 2323
4513 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191H-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 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C28H18N2O5V = 2286 (3) Å3
Mr = 462.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 21.069 (18) ŵ = 0.09 mm1
b = 6.063 (5) ÅT = 300 K
c = 18.727 (16) Å0.23 × 0.23 × 0.22 mm
β = 107.159 (13)°
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
2518 reflections with I > 2σ(I)
21331 measured reflectionsRint = 0.060
4513 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.191H-atom parameters constrained
S = 1.03Δρmax = 0.38 e Å3
4513 reflectionsΔρmin = 0.22 e Å3
316 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.53828 (13)1.1931 (4)0.31832 (14)0.1027 (11)
O20.76931 (12)0.6953 (4)0.21732 (12)0.0864 (9)
O30.84189 (14)0.9715 (5)0.25694 (17)0.1262 (12)
O40.29559 (10)0.7471 (3)0.52085 (12)0.0762 (8)
O50.25276 (10)0.4910 (4)0.43300 (12)0.0811 (8)
N10.48512 (12)1.1945 (4)0.35022 (14)0.0723 (10)
N20.53434 (12)0.8645 (4)0.36922 (13)0.0652 (9)
C10.56466 (16)0.9925 (5)0.33120 (16)0.0686 (11)
C20.48632 (15)0.9947 (5)0.37851 (16)0.0662 (11)
C30.62017 (15)0.9293 (5)0.30344 (16)0.0671 (11)
C40.64460 (17)1.0655 (5)0.25813 (18)0.0801 (12)
C50.69506 (19)0.9989 (6)0.23065 (18)0.0837 (14)
C60.72168 (16)0.7925 (6)0.24910 (17)0.0753 (11)
C70.69841 (17)0.6508 (6)0.29357 (19)0.0867 (14)
C80.64812 (17)0.7210 (6)0.32118 (19)0.0828 (12)
C90.8266 (2)0.7982 (6)0.22570 (19)0.0887 (14)
C100.87083 (16)0.6675 (6)0.19119 (17)0.0716 (11)
C110.9304 (2)0.7655 (7)0.1915 (2)0.1027 (17)
C120.9727 (2)0.6540 (10)0.1601 (3)0.135 (3)
C130.9549 (3)0.4485 (10)0.1288 (3)0.133 (3)
C140.8977 (2)0.3540 (7)0.1302 (2)0.1070 (17)
C150.85597 (18)0.4614 (6)0.16063 (19)0.0853 (12)
C160.43672 (14)0.9309 (5)0.41587 (16)0.0626 (10)
C170.38540 (16)1.0725 (5)0.41790 (18)0.0765 (11)
C180.33900 (16)1.0085 (5)0.45203 (18)0.0768 (12)
C190.34337 (14)0.8044 (5)0.48421 (17)0.0669 (11)
C200.39386 (14)0.6606 (5)0.48425 (17)0.0707 (11)
C210.44033 (14)0.7249 (5)0.44904 (18)0.0712 (11)
C220.25088 (13)0.5876 (5)0.48832 (17)0.0610 (10)
C230.20080 (14)0.5533 (5)0.52860 (15)0.0637 (10)
C240.18931 (16)0.7044 (6)0.57868 (19)0.0821 (12)
C250.14077 (19)0.6633 (7)0.6137 (2)0.1033 (17)
C260.1046 (2)0.4723 (8)0.5987 (2)0.1142 (19)
C270.1155 (2)0.3225 (7)0.5490 (2)0.1099 (17)
C280.16333 (17)0.3616 (6)0.51374 (19)0.0847 (12)
H40.626301.205200.246100.0960*
H50.710901.091500.200200.1010*
H70.716400.510400.304600.1040*
H80.632700.628400.352000.0990*
H110.941700.904200.212600.1230*
H121.012900.716900.159900.1620*
H130.982900.374800.106600.1590*
H140.886900.213900.110100.1280*
H150.816300.394500.160900.1020*
H170.382501.211300.396000.0920*
H180.304701.103600.453300.0920*
H200.396800.523600.507300.0850*
H210.474300.628600.447700.0860*
H240.214100.833700.589000.0980*
H250.132900.765300.647100.1240*
H260.072500.444300.622500.1370*
H270.090400.193700.538900.1320*
H280.170500.259200.480000.1010*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.124 (2)0.0824 (18)0.0989 (18)0.0007 (15)0.0286 (16)0.0218 (14)
O20.0992 (16)0.0847 (16)0.0788 (15)0.0287 (13)0.0317 (13)0.0061 (12)
O30.134 (2)0.108 (2)0.140 (2)0.0487 (18)0.0455 (19)0.0497 (19)
O40.0674 (13)0.0807 (14)0.0840 (15)0.0038 (11)0.0280 (12)0.0221 (12)
O50.0824 (14)0.0908 (15)0.0799 (14)0.0105 (12)0.0390 (12)0.0273 (13)
N10.0765 (17)0.0628 (16)0.0831 (17)0.0104 (13)0.0320 (14)0.0243 (13)
N20.0726 (16)0.0600 (15)0.0624 (15)0.0061 (13)0.0191 (13)0.0076 (12)
C10.080 (2)0.061 (2)0.0573 (17)0.0043 (17)0.0088 (16)0.0033 (15)
C20.0684 (19)0.0625 (19)0.0574 (17)0.0006 (16)0.0025 (15)0.0046 (15)
C30.081 (2)0.062 (2)0.0541 (16)0.0140 (16)0.0136 (15)0.0024 (14)
C40.103 (2)0.063 (2)0.076 (2)0.0104 (18)0.029 (2)0.0037 (17)
C50.117 (3)0.063 (2)0.079 (2)0.017 (2)0.041 (2)0.0073 (17)
C60.088 (2)0.080 (2)0.0610 (19)0.0149 (18)0.0268 (17)0.0039 (17)
C70.099 (3)0.078 (2)0.092 (2)0.0024 (19)0.042 (2)0.0207 (19)
C80.094 (2)0.083 (2)0.079 (2)0.002 (2)0.0375 (19)0.0237 (18)
C90.118 (3)0.070 (2)0.071 (2)0.036 (2)0.017 (2)0.0065 (18)
C100.077 (2)0.073 (2)0.0596 (18)0.0037 (17)0.0122 (16)0.0088 (16)
C110.086 (3)0.081 (3)0.126 (3)0.016 (2)0.008 (2)0.016 (2)
C120.072 (3)0.136 (4)0.199 (6)0.002 (3)0.043 (3)0.057 (4)
C130.103 (4)0.137 (5)0.164 (5)0.042 (3)0.049 (3)0.035 (4)
C140.100 (3)0.102 (3)0.107 (3)0.014 (3)0.012 (3)0.005 (2)
C150.083 (2)0.079 (2)0.085 (2)0.013 (2)0.0110 (19)0.003 (2)
C160.0580 (16)0.0601 (18)0.0608 (17)0.0017 (14)0.0040 (14)0.0029 (14)
C170.083 (2)0.0592 (19)0.079 (2)0.0108 (17)0.0112 (18)0.0068 (16)
C180.073 (2)0.065 (2)0.087 (2)0.0168 (16)0.0153 (18)0.0068 (17)
C190.0598 (18)0.063 (2)0.073 (2)0.0007 (15)0.0121 (15)0.0117 (16)
C200.0617 (18)0.0625 (19)0.087 (2)0.0075 (15)0.0204 (17)0.0120 (16)
C210.0599 (18)0.0613 (19)0.091 (2)0.0121 (14)0.0200 (17)0.0127 (16)
C220.0583 (17)0.0588 (17)0.0639 (18)0.0085 (14)0.0151 (15)0.0079 (15)
C230.0648 (18)0.0643 (19)0.0612 (17)0.0082 (15)0.0176 (15)0.0084 (15)
C240.080 (2)0.085 (2)0.085 (2)0.0062 (18)0.0301 (19)0.0206 (19)
C250.102 (3)0.120 (3)0.102 (3)0.004 (3)0.052 (2)0.040 (3)
C260.117 (3)0.135 (4)0.115 (3)0.013 (3)0.072 (3)0.025 (3)
C270.126 (3)0.108 (3)0.119 (3)0.032 (3)0.072 (3)0.025 (3)
C280.102 (2)0.078 (2)0.087 (2)0.006 (2)0.048 (2)0.0178 (19)
Geometric parameters (Å, º) top
O1—N11.416 (4)C18—C191.368 (4)
O1—C11.329 (4)C19—C201.375 (4)
O2—C61.436 (4)C20—C211.388 (5)
O2—C91.326 (5)C22—C231.482 (4)
O3—C91.200 (5)C23—C241.383 (5)
O4—C191.419 (4)C23—C281.386 (5)
O4—C221.362 (4)C24—C251.391 (5)
O5—C221.201 (4)C25—C261.369 (6)
N1—C21.319 (4)C26—C271.368 (6)
N2—C11.336 (4)C27—C281.379 (6)
N2—C21.335 (4)C4—H40.9300
C1—C31.464 (5)C5—H50.9300
C2—C161.471 (5)C7—H70.9300
C3—C41.387 (5)C8—H80.9300
C3—C81.392 (5)C11—H110.9300
C4—C51.372 (5)C12—H120.9300
C5—C61.373 (5)C13—H130.9300
C6—C71.383 (5)C14—H140.9300
C7—C81.376 (5)C15—H150.9300
C9—C101.506 (5)C17—H170.9300
C10—C111.387 (6)C18—H180.9300
C10—C151.372 (5)C20—H200.9300
C11—C121.381 (7)C21—H210.9300
C12—C131.381 (8)C24—H240.9300
C13—C141.342 (8)C25—H250.9300
C14—C151.348 (6)C26—H260.9300
C16—C171.390 (5)C27—H270.9300
C16—C211.387 (4)C28—H280.9300
C17—C181.372 (5)
N1—O1—C1105.6 (2)C22—C23—C24123.1 (3)
C6—O2—C9118.8 (3)C22—C23—C28117.7 (3)
C19—O4—C22117.0 (2)C24—C23—C28119.2 (3)
O1—N1—C2103.9 (2)C23—C24—C25120.1 (3)
C1—N2—C2103.1 (3)C24—C25—C26119.8 (4)
O1—C1—N2112.8 (3)C25—C26—C27120.4 (4)
O1—C1—C3120.7 (3)C26—C27—C28120.3 (4)
N2—C1—C3126.5 (3)C23—C28—C27120.1 (3)
N1—C2—N2114.6 (3)C3—C4—H4119.00
N1—C2—C16120.0 (3)C5—C4—H4119.00
N2—C2—C16125.4 (3)C4—C5—H5121.00
C1—C3—C4122.7 (3)C6—C5—H5121.00
C1—C3—C8118.6 (3)C6—C7—H7121.00
C4—C3—C8118.6 (3)C8—C7—H7121.00
C3—C4—C5121.5 (3)C3—C8—H8120.00
C4—C5—C6118.6 (3)C7—C8—H8120.00
O2—C6—C5123.6 (3)C10—C11—H11120.00
O2—C6—C7114.2 (3)C12—C11—H11120.00
C5—C6—C7121.8 (3)C11—C12—H12120.00
C6—C7—C8118.9 (3)C13—C12—H12120.00
C3—C8—C7120.6 (3)C12—C13—H13120.00
O2—C9—O3125.0 (4)C14—C13—H13120.00
O2—C9—C10111.0 (3)C13—C14—H14120.00
O3—C9—C10124.0 (4)C15—C14—H14120.00
C9—C10—C11116.5 (3)C10—C15—H15119.00
C9—C10—C15124.4 (3)C14—C15—H15119.00
C11—C10—C15119.1 (3)C16—C17—H17120.00
C10—C11—C12119.0 (4)C18—C17—H17120.00
C11—C12—C13119.6 (5)C17—C18—H18120.00
C12—C13—C14120.7 (5)C19—C18—H18120.00
C13—C14—C15120.2 (4)C19—C20—H20121.00
C10—C15—C14121.3 (4)C21—C20—H20121.00
C2—C16—C17121.2 (3)C16—C21—H21120.00
C2—C16—C21119.8 (3)C20—C21—H21120.00
C17—C16—C21119.0 (3)C23—C24—H24120.00
C16—C17—C18120.3 (3)C25—C24—H24120.00
C17—C18—C19119.8 (3)C24—C25—H25120.00
O4—C19—C18118.0 (3)C26—C25—H25120.00
O4—C19—C20120.2 (3)C25—C26—H26120.00
C18—C19—C20121.7 (3)C27—C26—H26120.00
C19—C20—C21118.4 (3)C26—C27—H27120.00
C16—C21—C20120.8 (3)C28—C27—H27120.00
O4—C22—O5122.5 (3)C23—C28—H28120.00
O4—C22—C23112.0 (2)C27—C28—H28120.00
O5—C22—C23125.5 (3)
C1—O1—N1—C20.2 (3)O2—C9—C10—C11175.5 (3)
N1—O1—C1—N20.8 (3)O2—C9—C10—C154.9 (5)
N1—O1—C1—C3178.0 (3)O3—C9—C10—C115.0 (5)
C9—O2—C6—C559.1 (4)O3—C9—C10—C15174.6 (4)
C9—O2—C6—C7128.3 (3)C9—C10—C11—C12179.5 (4)
C6—O2—C9—O31.6 (5)C15—C10—C11—C120.9 (6)
C6—O2—C9—C10177.9 (3)C9—C10—C15—C14179.6 (3)
C22—O4—C19—C18111.2 (3)C11—C10—C15—C140.8 (5)
C22—O4—C19—C2071.4 (4)C10—C11—C12—C130.3 (7)
C19—O4—C22—O53.2 (4)C11—C12—C13—C141.6 (8)
C19—O4—C22—C23176.0 (2)C12—C13—C14—C151.7 (7)
O1—N1—C2—C16178.9 (3)C13—C14—C15—C100.5 (6)
O1—N1—C2—N20.5 (3)C2—C16—C17—C18179.0 (3)
C2—N2—C1—C3177.6 (3)C21—C16—C17—C180.2 (5)
C1—N2—C2—C16178.4 (3)C2—C16—C21—C20179.6 (3)
C2—N2—C1—O11.1 (3)C17—C16—C21—C200.4 (5)
C1—N2—C2—N11.0 (3)C16—C17—C18—C190.0 (5)
O1—C1—C3—C8177.1 (3)C17—C18—C19—O4178.2 (3)
N2—C1—C3—C4173.5 (3)C17—C18—C19—C200.8 (5)
N2—C1—C3—C84.2 (5)O4—C19—C20—C21178.7 (3)
O1—C1—C3—C45.1 (5)C18—C19—C20—C211.5 (5)
N1—C2—C16—C174.3 (4)C19—C20—C21—C161.2 (5)
N1—C2—C16—C21176.5 (3)O4—C22—C23—C2417.3 (4)
N2—C2—C16—C17175.0 (3)O4—C22—C23—C28163.9 (3)
N2—C2—C16—C214.1 (5)O5—C22—C23—C24161.9 (3)
C1—C3—C4—C5177.6 (3)O5—C22—C23—C2817.0 (5)
C8—C3—C4—C50.2 (5)C22—C23—C24—C25179.0 (3)
C1—C3—C8—C7177.1 (3)C28—C23—C24—C250.2 (5)
C4—C3—C8—C70.8 (5)C22—C23—C28—C27179.3 (3)
C3—C4—C5—C60.2 (5)C24—C23—C28—C270.4 (5)
C4—C5—C6—O2172.9 (3)C23—C24—C25—C260.3 (6)
C4—C5—C6—C70.8 (5)C24—C25—C26—C270.6 (6)
O2—C6—C7—C8174.1 (3)C25—C26—C27—C280.4 (6)
C5—C6—C7—C81.3 (5)C26—C27—C28—C230.1 (6)
C6—C7—C8—C31.3 (5)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C10–C15 ring.
D—H···AD—HH···AD···AD—H···A
C18—H18···O5i0.932.573.407 (5)150
C25—H25···O3ii0.932.343.222 (6)158
C28—H28···Cg3iii0.932.963.678 (5)135
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+2, z+1; (iii) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC28H18N2O5
Mr462.44
Crystal system, space groupMonoclinic, P21/c
Temperature (K)300
a, b, c (Å)21.069 (18), 6.063 (5), 18.727 (16)
β (°) 107.159 (13)
V3)2286 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.23 × 0.23 × 0.22
Data collection
DiffractometerOxford Diffraction Xcalibur Eos
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
21331, 4513, 2518
Rint0.060
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.191, 1.03
No. of reflections4513
No. of parameters316
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C10–C15 ring.
D—H···AD—HH···AD···AD—H···A
C18—H18···O5i0.93002.57003.407 (5)150.00
C25—H25···O3ii0.93002.34003.222 (6)158.00
C28—H28···Cg3iii0.93002.96003.678 (5)135.00
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+2, z+1; (iii) x+1, y1/2, 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

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science
First citationDhol, S. R., Bhimani, A. S., Khunt, R. C. & Parik, A. R. (2005). Indian J. Heterocycl. Chem. 15, 63–64.  CAS
First citationEmmerling, F., Orgzall, I., Reck, G., Schulz, B. W., Stackhause, S. & Schulz, B. (2006). J. Mol. Struct. 800, 74–84.  Web of Science CSD CrossRef CAS
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS IUCr Journals
First citationOxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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