4-[5-(4-Benzoyl­oxyphen­yl)-1,2,4-oxa­diazol-3-yl]phenyl benzoate

Manjunath, B.C.; Madan Kumar, S.; Vinay Kumar, K.S.; Prabhuswamy, M.; Sadashiva, M.P.; Lokanath, N.K.

doi:10.1107/S1600536813006922

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o543

doi:10.1107/S1600536813006922

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4-[5-(4-Benzoyloxyphenyl)-1,2,4-oxadiazol-3-yl]phenyl benzoate

B. C. Manjunath,^a S. Madan Kumar,^a K. S. Vinay Kumar,^b M. Prabhuswamy,^a M. P. Sadashiva ^b and N. K. Lokanath ^a ^*

^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 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

C₂₈H₁₈N₂O₅
M_r = 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)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.191
S = 1.03
4513 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −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	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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813006922/sj5303sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006922/sj5303Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813006922/sj5303Isup3.cml

checkCIF report

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···Cg2^iv 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)

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

	Fig. 1. ORTEP diagram of the title molecule with 50% probability ellipsoids.
	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

C₂₈H₁₈N₂O₅	F(000) = 960
M_r = 462.44	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.060
Graphite monochromator	θ_max = 26.0°, θ_min = 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 top

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(F_o²) + (0.0786P)² + 0.5948P] where P = (F_o² + 2F_c²)/3
4513 reflections	(Δ/σ)_max < 0.001
316 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₈H₁₈N₂O₅	V = 2286 (3) Å³
M_r = 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)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2518 reflections with I > 2σ(I)
21331 measured reflections	R_int = 0.060
4513 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.191	H-atom parameters constrained
S = 1.03	Δρ_max = 0.38 e Å⁻³
4513 reflections	Δρ_min = −0.22 e Å⁻³
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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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
Emmerling, 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 Google Scholar
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 4| April 2013| Page o543

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