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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160329
doi:10.1107/S2414314616003291

7-Hy­dr­oxy-3-(4-nitro­phen­yl)-2H-chromen-2-one

Shashikanth Walki,a S. Naveen,b S. Kenchanna,a K. M. Mahadevan,a M. N. Kumarac and N. K. Lokanathd*

aDepartment of Chemistry, Kuvempu University, P G Centre, Kadur 577 548, India, bInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, cDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysuru 570 005, India, and dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India
*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

Edited by A. J. Lough, University of Toronto, Canada (Received 18 February 2016; accepted 26 February 2016; online 4 March 2016)

In the title compound, C15H9NO5, the coumarin ring system is essentially planar, with a dihedral angle of 1.42 (10)° between the two fused rings. The mean plane of the coumarin ring system forms a dihedral angle of 36.10 (1)° with the nitro-substituted benzene ring. The nitro group is almost coplanar with the benzene ring to which it is bonded, with a maximum deviation of 0.014 (6) Å for all atoms in the nitro­benzene group. As in other reported coumarin compounds, there is asymmetry with respect to the O—C=O bond angles, with values of 113.6 (5) and 128.0 (5)°. In a similar way, the O—C—C and C—C—C angles at the junction of the two fused rings have values of 117.6 (5) and 123.7 (5)°, respectively. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, forming chains along [010]. In addition, weak C—H⋯O hydrogen bonds link these chains, forming a three-dimensional network.

CCDC reference: 1455917

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

A recent study reveals that many coumarin fluoro­phores have shown enhanced pure blue efficient electroluminescence with 2.7 and 4.1% of external quantum efficiency, respectively (Chen et al., 2003[Chen, C. T., Chiang, C. L., Lin, Y. C., Chan, L. H., Huang, C., Tsai, Z. W. & Chen, C. T. (2003). Org. Lett. 5, 1261-1264.]). Also certain high-efficiency blue electroluminescence based on coumarin derivatives is found as blue-emitting OLEDs and laser dyes (Yu et al., 2009[Yu, T., Zhang, P., Zhao, Y., Zhang, H., Meng, J. & Fan, D. (2009). Org. Electron. 10, 653-660.]; Serin et al., 2002[Serin, J., Schultze, X., Adronov, A. & Fréchet, J. M. J. (2002). Macromolecules, 35, 5396-5404.]). Based on the photo-physical properties of coumarins and as a part of our ongoing research on these mol­ecules (Harishkumar et al., 2012[Harishkumar, H. N., Mahadevan, K. M., Jagadeesh, N. M. & Kirankumar, N. M. (2012). Org. Comm. 5, 196-208.]; Mahadevan et al., 2013[Mahadevan, K. M., Harishkumar, H. N., Masagalli, J. N. & Srinivasa, H. T. (2013). Mol. Cryst. Liq. Cryst. 570, 20-35.]; Rajesha et al., 2012[Rajesha, Kiran Kumar, H. C., Bhoja Naik, H. S. & Mahadevan, K. M. (2012). Org. Chem. Indian J. 8, 34-40.]), the synthesis and crystal structure determination of the title compound are reported herein. The compound is currently being assessed for its photo-physical properties.

The mol­ecular structure of the title compound is shown in Fig. 1[link]. The coumarin ring system is essentially planar with a dihedral angle of 1.42 (10)° between the two fused rings. The mean plane of the coumarin ring system forms a dihedral angle of 36.10 (1)° with the nitro-substituted benzene ring. This value differs slightly from the reported value of 25.27 (9) Å for 8-eth­oxy-3-(4-nitro­phen­yl)-2H-chromen-2-one (Walki et al., 2015[Walki, S., Naveen, S., Kenchanna, S., Mahadevan, K. M., Kumara, M. N. & Lokanath, N. K. (2015). Acta Cryst. E71, o860-o861.]). The nitro group is almost coplanar with the phenyl ring with a maximum deviation in the nitro­benzene group of 0.014 (6) Å for C16. Electron localization is indicated by the C8=C9 bond with a length of 1.360 (7) Å. As in other coumarin compounds reported there is an asymmetry in the O—C=O bond angles with values for O1—C10—O11 of 113.6 (5)° and O11—C10—C9 of 128.0 (5)°. The bond angles, O1—C2—C3 and C8—C7—C6, at the junction of the two rings in the coumarin moiety are 117.6 (5)° and 123.7 (5)° respectively.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, with displacement ellipsoids for non-H atoms drawn at the 50% probability level.

In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, forming chains along [010]. In addition weak C—H⋯O hydrogen bonds link these chains, forming a three-dimensional network (Fig. 2[link], Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O12—H12⋯O11i 0.82 1.89 2.704 (6) 172
C3—H3⋯O11i 0.93 2.53 3.209 (7) 130
C5—H5⋯O21ii 0.93 2.47 3.244 (7) 141
C8—H8⋯O11iii 0.93 2.58 3.253 (6) 130
C14—H14⋯O20iv 0.93 2.40 3.325 (7) 170
C18—H18⋯O20v 0.93 2.49 3.370 (7) 158
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x, y-1, z; (iii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iv) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (v) [-x+{\script{1\over 2}}, -y+2, z-{\script{1\over 2}}].
[Figure 2]
Figure 2
The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as blue lines.

Synthesis and crystallization

A mixture of 0.43 g m (3.08 mmol) of 2,4-dihy­droxy benzaldehyde and 0.5 g m (3.08 mmol) of 4-nitro phenyl­aceto­nitrile was dissolved in ethanol (25 ml), followed by the addition of 0.525 g m (6.16 mmol) of piperidine. The reaction mixture was then stirred at room temperature for 3 h. The completion of the reaction was monitored by thin layer chromatography [petroleum ether and ethyl acetate (8:2 v/v)]. After the completion of the reaction, the reaction mixture was filtered and washed with di­ethyl­ether to yield a brown precipitate. The crude product obtained was refluxed with 10% acetic acid for 2 h and was filtered and washed with water. The product obtained was further purified by recrystallization using glacial acetic acid as solvent to form brown crystals, m.p. = 535–537 K, yield 91.6%.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C15H9NO5
Mr 283.23
Crystal system, space group Orthorhombic, P212121
Temperature (K) 296
a, b, c (Å) 7.0087 (9), 13.0242 (13), 13.6761 (17)
V (Å3) 1248.4 (3)
Z 4
Radiation type Cu Kα
μ (mm−1) 0.98
Crystal size (mm) 0.29 × 0.26 × 0.25
 
Data collection
Diffractometer Bruker X8 Proteum
Absorption correction Multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.765, 0.792
No. of measured, independent and observed [I > 2σ(I)] reflections 6307, 2037, 1279
Rint 0.124
(sin θ/λ)max (Å−1) 0.587
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.181, 0.98
No. of reflections 2037
No. of parameters 190
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.29, −0.35
Computer programs: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), 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.]).

Structural data

CCDC reference: 1455917

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616003291/lh4004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616003291/lh4004Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616003291/lh4004Isup3.cml

checkCIF report


Comment top

A recent study reveals that many coumarin fluorophores have shown enhanced pure blue efficient electroluminescence with 2.7% and 4.1% of external quantum efficiency respectively (Chen et al., 2003). Also certain high-efficiency blue electroluminescence based on coumarin derivatives is found as blue emitting OLEDs and laser dyes (Yu et al., 2009; Serin et al., 2002). Based on the brilliant photo physical properties of coumarins and as a part of our ongoing research on these molecules (Harishkumar et al., 2012; Mahadevan et al., 2013; Rajesha et al., 2012), the synthesis and crystal structure determination of the title compound is reported herein. The compound is currently being assessed for its photo physical properties.

The molecular structure of the title compound is shown in Fig. 1. The coumarin ring system is essentially planar with a dihedral angle of 1.42 (10) Å between the two fused rings. The mean plane of the coumarin ring system forms a dihedral angle of 36.10 (1) Å with the nitro-substituted benzene ring. This value differs slightly from the reported value of 25.27 (9) Å for 8-ethoxy-3-(4-nitrophenyl)-2H-chromen-2-one (Walki et al., 2015). The nitro group is almost planar to the phenyl ring with a maximum deviation in the nitrobenzene group of 0.014 (6) Å for C16. Electron localization is indicated by the C8═C9 bond with a length of 1.360 (7) Å. As in other coumarin compounds reported there is an asymmetry in the O—C═O bond angles with values for O1—C10—O11 of 113.6 (5)° and O11—C10—C9 of 128.0 (5)°. The bond angles, O1—C2—C3 and C8—C7—C6, at the junction of the two rings in the coumarin moiety are 117.6 (5)° and 123.7 (5)° respectively. In the crystal, molecules are linked by O—H···O hydrogen bonds forming chains along [010]. In addition weak C—H···O hydrogen bonds link these chains forming a three-dimensional network (Fig. 2, Table 2).

Experimental top

A mixture of 0.43 g m (3.08 mmol) of 2,4-dihydroxy benzaldehyde and 0.5 g m (3.08 mmol) of 4-nitro phenylacetonitrile was dissolved in ethanol (25 ml), followed by the addition of 0.525 g m (6.16 mmol) of piperidine. The reaction mixture was then stirred at room temperature for 3 h. The completion of the reaction was monitored by thin layer chromatography [petroleum ether and ethyl acetate (8:2 v/v)]. After the completion of the reaction, the reaction mixture was filtered and washed with diethylether to yield a brown precipitate. The crude product obtained was refluxed with 10% acetic acid for 2 h and was filtered and washed with water. The product obtained was further purified by recrystallization using glacial acetic acid as solvent to form brown crystals, m.p. = 535–537 K, yield 91.6%.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2.

Structure description top

A recent study reveals that many coumarin fluorophores have shown enhanced pure blue efficient electroluminescence with 2.7 and 4.1% of external quantum efficiency, respectively (Chen et al., 2003). Also certain high-efficiency blue electroluminescence based on coumarin derivatives is found as blue-emitting OLEDs and laser dyes (Yu et al., 2009; Serin et al., 2002). Based on the photo-physical properties of coumarins and as a part of our ongoing research on these molecules (Harishkumar et al., 2012; Mahadevan et al., 2013; Rajesha et al., 2012), the synthesis and crystal structure determination of the title compound is reported herein. The compound is currently being assessed for its photo-physical properties.

The molecular structure of the title compound is shown in Fig. 1. The coumarin ring system is essentially planar with a dihedral angle of 1.42 (10) Å between the two fused rings. The mean plane of the coumarin ring system forms a dihedral angle of 36.10 (1) Å with the nitro-substituted benzene ring. This value differs slightly from the reported value of 25.27 (9) Å for 8-ethoxy-3-(4-nitrophenyl)-2H-chromen-2-one (Walki et al., 2015). The nitro group is almost coplanar with the phenyl ring with a maximum deviation in the nitrobenzene group of 0.014 (6) Å for C16. Electron localization is indicated by the C8═C9 bond with a length of 1.360 (7) Å. As in other coumarin compounds reported there is an asymmetry in the O—C═ O bond angles with values for O1—C10—O11 of 113.6 (5)° and O11—C10—C9 of 128.0 (5)°. The bond angles, O1—C2—C3 and C8—C7—C6, at the junction of the two rings in the coumarin moiety are 117.6 (5)° and 123.7 (5)° respectively.

In the crystal, molecules are linked by O—H···O hydrogen bonds, forming chains along [010]. In addition weak C—H···O hydrogen bonds link these chains, forming a three-dimensional network (Fig. 2, Table 1).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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: Mercury (Macrae et al., 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids for non-H atoms drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as blue lines.
7-Hydroxy-3-(4-nitrophenyl)-2H-chromen-2-one top
Crystal data top
C15H9NO5F(000) = 584
Mr = 283.23Dx = 1.507 Mg m−3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 2037 reflections
a = 7.0087 (9) Åθ = 4.7–64.9°
b = 13.0242 (13) ŵ = 0.98 mm−1
c = 13.6761 (17) ÅT = 296 K
V = 1248.4 (3) Å3Rectangle, brown
Z = 40.29 × 0.26 × 0.25 mm
Data collection top
Bruker X8 Proteum
diffractometer		2037 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode1279 reflections with I > 2σ(I)
Helios multilayer optics monochromatorRint = 0.124
Detector resolution: 18.4 pixels mm-1θmax = 64.9°, θmin = 4.7°
φ and ω scansh = −7→8
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		k = −15→14
Tmin = 0.765, Tmax = 0.792l = −15→14
6307 measured 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) = 0.181H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0812P)2]
where P = (Fo2 + 2Fc2)/3
2037 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.35 e Å−3
Crystal data top
C15H9NO5V = 1248.4 (3) Å3
Mr = 283.23Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 7.0087 (9) ŵ = 0.98 mm−1
b = 13.0242 (13) ÅT = 296 K
c = 13.6761 (17) Å0.29 × 0.26 × 0.25 mm
Data collection top
Bruker X8 Proteum
diffractometer		2037 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		1279 reflections with I > 2σ(I)
Tmin = 0.765, Tmax = 0.792Rint = 0.124
6307 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.181H-atom parameters constrained
S = 0.98Δρmax = 0.28 e Å−3
2037 reflectionsΔρmin = −0.35 e Å−3
190 parameters
Special details top

Experimental. 1H NMR(400 MHz, DMSO-d6 δ p.p.m.)10.79 (s, 1H), 8.40 (s, 1H), 8.28–8.29 (m, 2H), 8.0–8.02(m, 2H), 7.65(d, J= 8.40 Hz, 1H), 6.84–6.85 (m, 1H), 6.78 (d, J= 2.0 Hz, 1H).

IR (KBr) (vmax/cm−1): 3180 (C—OH), 2925 (C—H), 1678 (C=O), 1346 (N—O), 1127 (C—O—C).

Mass spectra of the compound showed molecular ion peak at m/z = 282.4 [M+].

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
O10.4270 (5)0.6104 (2)0.3410 (3)0.0301 (11)
O110.4770 (5)0.7766 (2)0.3319 (3)0.0322 (11)
O120.3610 (6)0.2463 (2)0.3452 (3)0.0409 (15)
O200.4326 (6)1.0871 (3)0.7822 (3)0.0447 (16)
O210.3441 (6)1.1717 (3)0.6546 (3)0.0472 (15)
N190.3856 (6)1.0912 (3)0.6965 (4)0.0340 (18)
C20.3786 (7)0.5216 (4)0.3899 (4)0.0253 (19)
C30.3933 (7)0.4300 (4)0.3393 (5)0.0307 (17)
C40.3449 (8)0.3408 (4)0.3889 (5)0.0303 (19)
C50.2816 (8)0.3427 (4)0.4851 (4)0.035 (2)
C60.2686 (8)0.4342 (4)0.5349 (5)0.035 (2)
C70.3205 (8)0.5259 (4)0.4875 (4)0.0290 (18)
C80.3137 (7)0.6256 (4)0.5334 (4)0.0287 (19)
C90.3675 (7)0.7127 (4)0.4860 (4)0.0277 (19)
C100.4251 (7)0.7064 (4)0.3859 (4)0.0307 (19)
C130.3718 (7)0.8134 (4)0.5380 (4)0.0267 (18)
C140.4250 (7)0.8149 (4)0.6359 (4)0.0313 (19)
C150.4280 (7)0.9056 (4)0.6883 (4)0.0313 (19)
C160.3772 (8)0.9957 (4)0.6398 (4)0.0300 (19)
C170.3265 (8)0.9975 (4)0.5432 (4)0.0310 (19)
C180.3210 (7)0.9055 (4)0.4914 (4)0.0310 (19)
H30.434000.428300.274600.0370*
H50.247800.281800.516100.0420*
H60.225900.435400.599300.0420*
H80.271100.630500.597700.0340*
H120.400800.253400.289200.0610*
H140.459000.753800.666600.0370*
H150.462900.906600.753900.0370*
H170.296201.059200.512600.0370*
H180.283900.905100.426100.0370*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.042 (2)0.0174 (16)0.031 (2)−0.0023 (15)0.0015 (18)−0.0052 (16)
O110.043 (2)0.0205 (17)0.033 (2)−0.0011 (16)0.0050 (19)0.0039 (18)
O120.072 (3)0.0176 (17)0.033 (3)−0.0035 (18)0.007 (2)−0.0074 (16)
O200.071 (3)0.027 (2)0.036 (3)−0.004 (2)−0.007 (2)−0.0086 (18)
O210.077 (3)0.0196 (19)0.045 (3)0.005 (2)−0.004 (2)0.002 (2)
N190.044 (3)0.020 (2)0.038 (4)−0.002 (2)0.001 (2)−0.006 (2)
C20.027 (3)0.020 (3)0.029 (4)−0.004 (2)0.000 (2)0.009 (2)
C30.040 (3)0.023 (3)0.029 (3)0.002 (3)0.005 (3)−0.001 (3)
C40.039 (3)0.016 (3)0.036 (4)0.000 (3)−0.001 (3)−0.006 (2)
C50.051 (4)0.021 (3)0.032 (4)−0.003 (3)0.006 (3)0.003 (3)
C60.050 (4)0.024 (3)0.031 (4)−0.001 (3)0.000 (3)−0.001 (3)
C70.037 (3)0.020 (2)0.030 (4)0.001 (2)0.003 (3)−0.001 (2)
C80.034 (3)0.026 (3)0.026 (4)−0.003 (2)0.001 (2)0.001 (2)
C90.036 (3)0.019 (3)0.028 (4)−0.005 (2)0.003 (2)−0.005 (2)
C100.031 (3)0.026 (3)0.035 (4)0.004 (2)−0.002 (3)−0.001 (3)
C130.032 (3)0.015 (2)0.033 (4)−0.001 (2)0.000 (2)0.000 (2)
C140.037 (3)0.023 (3)0.034 (4)0.001 (2)0.002 (3)0.000 (2)
C150.041 (3)0.023 (3)0.030 (4)−0.001 (3)−0.001 (3)−0.001 (2)
C160.034 (3)0.024 (3)0.032 (4)−0.002 (2)−0.002 (3)−0.004 (2)
C170.033 (3)0.021 (3)0.039 (4)0.001 (2)−0.005 (3)0.001 (3)
C180.035 (3)0.024 (3)0.034 (4)0.006 (3)−0.005 (3)−0.002 (3)
Geometric parameters (Å, º) top
O1—C21.378 (6)C9—C101.430 (8)
O1—C101.393 (6)C9—C131.492 (7)
O11—C101.230 (6)C13—C181.404 (7)
O12—C41.373 (6)C13—C141.390 (8)
O20—N191.219 (7)C14—C151.382 (7)
O21—N191.230 (6)C15—C161.394 (7)
O12—H120.8200C16—C171.368 (8)
N19—C161.467 (7)C17—C181.393 (7)
C2—C31.383 (8)C3—H30.9300
C2—C71.397 (8)C5—H50.9300
C3—C41.387 (8)C6—H60.9300
C4—C51.389 (9)C8—H80.9300
C5—C61.376 (8)C14—H140.9300
C6—C71.407 (8)C15—H150.9300
C7—C81.443 (7)C17—H170.9300
C8—C91.360 (7)C18—H180.9300
C2—O1—C10122.5 (4)C14—C13—C18119.6 (5)
C4—O12—H12109.00C9—C13—C14118.5 (5)
O20—N19—O21123.3 (4)C13—C14—C15121.0 (5)
O21—N19—C16117.9 (5)C14—C15—C16118.0 (5)
O20—N19—C16118.8 (4)N19—C16—C15116.9 (5)
O1—C2—C7120.1 (5)N19—C16—C17120.4 (5)
C3—C2—C7122.3 (5)C15—C16—C17122.7 (5)
O1—C2—C3117.6 (5)C16—C17—C18118.9 (5)
C2—C3—C4117.4 (6)C13—C18—C17119.8 (5)
O12—C4—C5117.0 (5)C2—C3—H3121.00
C3—C4—C5121.8 (5)C4—C3—H3121.00
O12—C4—C3121.2 (6)C4—C5—H5120.00
C4—C5—C6120.4 (5)C6—C5—H5120.00
C5—C6—C7119.4 (6)C5—C6—H6120.00
C2—C7—C6118.8 (5)C7—C6—H6120.00
C2—C7—C8117.5 (5)C7—C8—H8119.00
C6—C7—C8123.7 (5)C9—C8—H8119.00
C7—C8—C9122.3 (5)C13—C14—H14119.00
C8—C9—C10119.1 (5)C15—C14—H14120.00
C10—C9—C13120.1 (5)C14—C15—H15121.00
C8—C9—C13120.8 (5)C16—C15—H15121.00
O1—C10—C9118.5 (5)C16—C17—H17121.00
O11—C10—C9128.0 (5)C18—C17—H17121.00
O1—C10—O11113.6 (5)C13—C18—H18120.00
C9—C13—C18122.0 (5)C17—C18—H18120.00
C10—O1—C2—C3−177.3 (4)C2—C7—C8—C9−2.3 (8)
C10—O1—C2—C71.6 (7)C7—C8—C9—C102.8 (8)
C2—O1—C10—O11178.3 (4)C7—C8—C9—C13−175.6 (5)
C2—O1—C10—C9−1.1 (7)C8—C9—C13—C1435.2 (7)
O20—N19—C16—C17−179.5 (5)C8—C9—C13—C18−143.7 (5)
O20—N19—C16—C15−1.2 (7)C10—C9—C13—C14−143.1 (5)
O21—N19—C16—C15178.9 (5)C10—C9—C13—C1837.9 (7)
O21—N19—C16—C170.7 (7)C8—C9—C10—O1−1.1 (7)
O1—C2—C3—C4179.8 (5)C8—C9—C10—O11179.7 (5)
C3—C2—C7—C8178.9 (5)C13—C9—C10—O1177.3 (4)
C3—C2—C7—C6−2.3 (8)C13—C9—C10—O11−2.0 (8)
C7—C2—C3—C41.0 (8)C9—C13—C14—C15−178.7 (5)
O1—C2—C7—C6178.8 (5)C18—C13—C14—C150.3 (8)
O1—C2—C7—C80.1 (7)C9—C13—C18—C17179.7 (5)
C2—C3—C4—C50.9 (8)C14—C13—C18—C170.8 (7)
C2—C3—C4—O12−178.0 (5)C13—C14—C15—C16−0.4 (8)
O12—C4—C5—C6177.6 (5)C14—C15—C16—N19−178.7 (5)
C3—C4—C5—C6−1.3 (9)C14—C15—C16—C17−0.5 (8)
C4—C5—C6—C7−0.2 (9)N19—C16—C17—C18179.7 (5)
C5—C6—C7—C21.9 (8)C15—C16—C17—C181.5 (8)
C5—C6—C7—C8−179.4 (5)C16—C17—C18—C13−1.6 (8)
C6—C7—C8—C9179.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O11i0.821.892.704 (6)172
C3—H3···O11i0.932.533.209 (7)130
C5—H5···O21ii0.932.473.244 (7)141
C8—H8···O11iii0.932.583.253 (6)130
C14—H14···O20iv0.932.403.325 (7)170
C18—H18···O110.932.512.962 (6)110
C18—H18···O20v0.932.493.370 (7)158
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) x−1/2, −y+3/2, −z+1; (iv) −x+1, y−1/2, −z+3/2; (v) −x+1/2, −y+2, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O11i0.82001.89002.704 (6)172.00
C3—H3···O11i0.93002.53003.209 (7)130.00
C5—H5···O21ii0.93002.47003.244 (7)141.00
C8—H8···O11iii0.93002.58003.253 (6)130.00
C14—H14···O20iv0.93002.40003.325 (7)170.00
C18—H18···O20v0.93002.49003.370 (7)158.00
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) x−1/2, −y+3/2, −z+1; (iv) −x+1, y−1/2, −z+3/2; (v) −x+1/2, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formulaC15H9NO5
Mr283.23
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)7.0087 (9), 13.0242 (13), 13.6761 (17)
V (Å3)1248.4 (3)
Z4
Radiation typeCu Kα
µ (mm−1)0.98
Crystal size (mm)0.29 × 0.26 × 0.25
Data collection
DiffractometerBruker X8 Proteum
Absorption correctionMulti-scan
(SADABS; Bruker, 2013)
Tmin, Tmax0.765, 0.792
No. of measured, independent and
observed [I > 2σ(I)] reflections		6307, 2037, 1279
Rint0.124
(sin θ/λ)max (Å−1)0.587
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.181, 0.98
No. of reflections2037
No. of parameters190
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.28, −0.35

Computer programs: APEX2 (Bruker, 2013), SAINT (Bruker, 2013), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

 

Acknowledgements

The authors are thankful to the IOE, Vijnana Bhavana, University of Mysore, for providing the single-crystal X-ray diffractometer facility. The authors acknowledge financial support received from the DST, New Delhi, under SERB reference No. SB/EMEQ-351/2013 (dated 29–10-2013).

References

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Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160329
doi:10.1107/S2414314616003291
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