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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o860-o861
https://doi.org/10.1107/S2056989015019325

Crystal structure of 8-eth­­oxy-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, Mysore 570 006, India, cDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India, and dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 9 October 2015; accepted 12 October 2015; online 17 October 2015)

In the title compound, C17H13NO5, the coumarin ring system is essentially planar (r.m.s. deviation = 0.008 Å). The nitro­phenyl ring makes a dihedral angle of 25.27 (9)° with the coumarin ring plane. The nitro group is almost coplanar with the phenyl ring to which it is attached, making a dihedral angle of 4.3 (3)°. The eth­oxy group is inclined to the coumarin ring plane by 4.1 (2)°. Electron delocalization was found at the short bridging C—C bond with a bond length of 1.354 (2) Å. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming sheets in the bc plane. The sheets are linked via π–π stacking [centroid–centroid distances = 3.5688 (13) and 3.7514 (13) Å], forming a three-dimensional structure.

CCDC reference: 1430858

Similar articles

1. Related literature

For coumarin derivatives as fluorescent brighteners, see: Tian et al. (2000[Tian, Y., Akiyama, E., Nagase, Y., Kanazawa, A., Tsutsumi, O. & Ikeda, T. (2000). Macromol. Chem. Phys. 201, 1640-1652.]). For details of natural or synthetic coumarins which inhibit lipid peroxidation and scavenge hydroxyl radicals and superoxide anions, see: Naveen et al. (2007[Naveen, S., Lakshmi, S., Manvar, D., Parecha, A., Shah, A., Sridhar, M. A. & Shashidhara Prasad, J. (2007). J. Chem. Crystallogr. 37, 733-738.]). For further details of our research on coumarins, see: Naveen et al. (2006a[Naveen, S., Dinesh, M., Alpesh, P., Shah, A., Sridhar, M. A. & Shashidhara Prasad, J. (2006a). J. Anal. Sci. 22, x101-x102.],b[Naveen, S., Priti, A., Kuldip, U., Shah, A., Sridhar, M. A. & Shashidhara Prasad, J. (2006b). J. Anal. Sci. 22, x103-x104.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C17H13NO5

  • Mr = 311.28

  • Orthorhombic, P 21 21 21

  • a = 6.8118 (9) Å

  • b = 13.6726 (18) Å

  • c = 15.909 (2) Å

  • V = 1481.7 (3) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.87 mm−1

  • T = 296 K

  • 0.29 × 0.26 × 0.21 mm

2.2. Data collection

  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.786, Tmax = 0.838

  • 6729 measured reflections

  • 2371 independent reflections

  • 2225 reflections with I > 2σ(I)

  • Rint = 0.040

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.131

  • S = 1.03

  • 2371 reflections

  • 210 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.21 e Å−3

  • Absolute structure: 957 Friedel pairs; Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.])

  • Absolute structure parameter: 0.1 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C4—H4⋯O22i 0.93 2.53 3.453 (2) 171
C8—H8⋯O14ii 0.93 2.31 3.226 (2) 166
C20—H20⋯O22i 0.93 2.52 3.275 (3) 138
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1430858

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015019325/su5224sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019325/su5224Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015019325/su5224Isup3.cml

checkCIF report


Comment top

Coumarin derivatives are found to be one of the major groups of compounds used as fluorescent brighteners (Tian et al., 2000) or fluorescent dyes and they have exhibited good bleed fastness and durability for coating plastics or in acrylic lacquers. Several natural or synthetic coumarins with various hydroxyl and other substituents were found to inhibit lipid peroxidation and to scavenge hydroxyl radicals and superoxide anions (Naveen et al., 2007). As a part of our ongoing research on coumarins (Naveen et al., 2006a,b), we report herein on the synthesis, characterization and crystal structure of the title compound. The compound is being assessed for biological activity.

The molecular structure of the title compound is shown in Fig. 1. The coumarin ring is essentially planar with the two axially fused rings forming a dihedral angle of 0.45 (10) °, while the 4-nitro­phenyl ring makes a dihedral angle of 25.27 (9) Å with the coumarin mean plane. The nitro group is almost planar to the phenyl ring to which it is attached with a dihedral angle of 4.3 (3) °. The eth­oxy group is inclined to the coumarin ring plane by 4.1 (2) °.

Electron delocalization was found at the short C3—C4 bond with a bond length of 1.354 (2) Å. Here as well as in other coumarin compounds reported earlier an important asymmetry in the O—C—O bond angle was detected [O1—C2—O14 = 116.10 (14)° and O14—C2—C3 = 126.14 (15)°]. The bond angles, O1—C10—C9 and C4—C5—C6, at the junction of the two rings in the coumarin moiety are 117.97 (15)° and 123.44 (16)° respectively.

In the crystal, molecules are linked via C–H···O hydrogen bonds forming sheets in the bc plane. The sheets are linked via π-π inter­actions [Cg1···Cg3i = 3.5688 (13) Å; Cg1···Cg3ii = 3.75114 (13) Å; Cg1 and Cg3 are the centroids of rings O1/C2—C5/C10 and C15—C20; symmetry codes: (i) x-1/2, -y+3/2, -z+1; (ii) x+1/2, -y+3/2, -z+1] forming a three-dimensional structure (Table 1 and Fig. 2)

Synthesis and crystallization top

A mixture of 0.512 g m (3.083 mmol) of 3-eth­oxy­salicyl­aldehyde and 0.50 g m (3.083 mmol) of 4-nitro phenyl­aceto­nitrile were dissolved in ethanol (25 ml), followed by the addition of 0.525 g m (6.16 mmol) of piperidine and then the reaction mixture was 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 completion the reaction mixture was filtered and washed with di­ethyl­ether giving a yellow precipitation. This product was refluxed with 10% acetic acid for 2 s and then the crude product was filtered and washed with water. It was further purified by recrystallization using acetone as solvent to give yellow crystals of the title compound in good yield (m.p.: 475-477 K; yield: 91%). 1H NMR(400 MHz, DMSO-d6): δ = 8.47 (s, 1H, Ar—H), 8.34 (dd, J= 2.08 Hz, 6.94 Hz, 2H, Ar—H), 8.05 (dd, J=2.0 Hz, 6.96 Hz, 2H, Ar—H), 7.34–7.36(m, 3H, Ar—H), 4.22(q, J= 6.92 Hz, 2H, CH2), 1.43(t, J=6.96 Hz,3H, CH3). 13C NMR (400 MHz, DMSO-d6): δ = 45.554, 142.927, 145.554, 142.927, 129.804, 124.807, 123.375, 120.205, 119.868, 115.603, 64.470, 14.63. IR (KBr) (vmax/cm-1): 2925 (C—H), 1700 (C=O), 1346 (N—O), 1097 (C—O—C). Mass spectra gave a molecular ion peak at m/z = 311.4[M+].

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The hydrogen atom were fixed geometrically (C—H= 0.93–0.96 Å) and allowed to ride on their parent atoms with Uiso(H) =1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.

Related literature top

For coumarin derivatives as fluorescent brighteners, see: Tian et al. (2000). For details of natural or synthetic coumarins which inhibit lipid peroxidation and scavenge hydroxyl radicals and superoxide anions, see: Naveen et al. (2007). For further details of our research on coumarins, see: Naveen et al. (2006a,b).

Structure description top

Coumarin derivatives are found to be one of the major groups of compounds used as fluorescent brighteners (Tian et al., 2000) or fluorescent dyes and they have exhibited good bleed fastness and durability for coating plastics or in acrylic lacquers. Several natural or synthetic coumarins with various hydroxyl and other substituents were found to inhibit lipid peroxidation and to scavenge hydroxyl radicals and superoxide anions (Naveen et al., 2007). As a part of our ongoing research on coumarins (Naveen et al., 2006a,b), we report herein on the synthesis, characterization and crystal structure of the title compound. The compound is being assessed for biological activity.

The molecular structure of the title compound is shown in Fig. 1. The coumarin ring is essentially planar with the two axially fused rings forming a dihedral angle of 0.45 (10) °, while the 4-nitro­phenyl ring makes a dihedral angle of 25.27 (9) Å with the coumarin mean plane. The nitro group is almost planar to the phenyl ring to which it is attached with a dihedral angle of 4.3 (3) °. The eth­oxy group is inclined to the coumarin ring plane by 4.1 (2) °.

Electron delocalization was found at the short C3—C4 bond with a bond length of 1.354 (2) Å. Here as well as in other coumarin compounds reported earlier an important asymmetry in the O—C—O bond angle was detected [O1—C2—O14 = 116.10 (14)° and O14—C2—C3 = 126.14 (15)°]. The bond angles, O1—C10—C9 and C4—C5—C6, at the junction of the two rings in the coumarin moiety are 117.97 (15)° and 123.44 (16)° respectively.

In the crystal, molecules are linked via C–H···O hydrogen bonds forming sheets in the bc plane. The sheets are linked via π-π inter­actions [Cg1···Cg3i = 3.5688 (13) Å; Cg1···Cg3ii = 3.75114 (13) Å; Cg1 and Cg3 are the centroids of rings O1/C2—C5/C10 and C15—C20; symmetry codes: (i) x-1/2, -y+3/2, -z+1; (ii) x+1/2, -y+3/2, -z+1] forming a three-dimensional structure (Table 1 and Fig. 2)

For coumarin derivatives as fluorescent brighteners, see: Tian et al. (2000). For details of natural or synthetic coumarins which inhibit lipid peroxidation and scavenge hydroxyl radicals and superoxide anions, see: Naveen et al. (2007). For further details of our research on coumarins, see: Naveen et al. (2006a,b).

Synthesis and crystallization top

A mixture of 0.512 g m (3.083 mmol) of 3-eth­oxy­salicyl­aldehyde and 0.50 g m (3.083 mmol) of 4-nitro phenyl­aceto­nitrile were dissolved in ethanol (25 ml), followed by the addition of 0.525 g m (6.16 mmol) of piperidine and then the reaction mixture was 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 completion the reaction mixture was filtered and washed with di­ethyl­ether giving a yellow precipitation. This product was refluxed with 10% acetic acid for 2 s and then the crude product was filtered and washed with water. It was further purified by recrystallization using acetone as solvent to give yellow crystals of the title compound in good yield (m.p.: 475-477 K; yield: 91%). 1H NMR(400 MHz, DMSO-d6): δ = 8.47 (s, 1H, Ar—H), 8.34 (dd, J= 2.08 Hz, 6.94 Hz, 2H, Ar—H), 8.05 (dd, J=2.0 Hz, 6.96 Hz, 2H, Ar—H), 7.34–7.36(m, 3H, Ar—H), 4.22(q, J= 6.92 Hz, 2H, CH2), 1.43(t, J=6.96 Hz,3H, CH3). 13C NMR (400 MHz, DMSO-d6): δ = 45.554, 142.927, 145.554, 142.927, 129.804, 124.807, 123.375, 120.205, 119.868, 115.603, 64.470, 14.63. IR (KBr) (vmax/cm-1): 2925 (C—H), 1700 (C=O), 1346 (N—O), 1097 (C—O—C). Mass spectra gave a molecular ion peak at m/z = 311.4[M+].

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. The hydrogen atom were fixed geometrically (C—H= 0.93–0.96 Å) and allowed to ride on their parent atoms with Uiso(H) =1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.

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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A viewed along the b axis of the crystal packing of the title compound.
8-Ethoxy-3-(4-nitrophenyl)-2H-chromen-2-one top
Crystal data top
C17H13NO5F(000) = 648
Mr = 311.28Dx = 1.395 Mg m−3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 2371 reflections
a = 6.8118 (9) Åθ = 5.6–64.1°
b = 13.6726 (18) ŵ = 0.87 mm−1
c = 15.909 (2) ÅT = 296 K
V = 1481.7 (3) Å3Prism, yellow
Z = 40.29 × 0.26 × 0.21 mm
Data collection top
Bruker X8 Proteum
diffractometer		2371 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode2225 reflections with I > 2σ(I)
Helios multilayer optics monochromatorRint = 0.040
Detector resolution: 18.4 pixels mm-1θmax = 64.1°, θmin = 5.6°
φ and ω scansh = −7→6
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		k = −15→15
Tmin = 0.786, Tmax = 0.838l = −18→18
6729 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045 w = 1/[σ2(Fo2) + (0.103P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.131(Δ/σ)max = 0.003
S = 1.03Δρmax = 0.25 e Å−3
2371 reflectionsΔρmin = −0.21 e Å−3
210 parametersExtinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
0 restraintsExtinction coefficient: 0.0100 (19)
Primary atom site location: structure-invariant direct methodsAbsolute structure: 957 Friedel pairs; Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.1 (2)
Crystal data top
C17H13NO5V = 1481.7 (3) Å3
Mr = 311.28Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 6.8118 (9) ŵ = 0.87 mm−1
b = 13.6726 (18) ÅT = 296 K
c = 15.909 (2) Å0.29 × 0.26 × 0.21 mm
Data collection top
Bruker X8 Proteum
diffractometer		2371 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		2225 reflections with I > 2σ(I)
Tmin = 0.786, Tmax = 0.838Rint = 0.040
6729 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.131Δρmax = 0.25 e Å−3
S = 1.03Δρmin = −0.21 e Å−3
2371 reflectionsAbsolute structure: 957 Friedel pairs; Flack (1983)
210 parametersAbsolute structure parameter: 0.1 (2)
0 restraints
Special details top

Experimental. Commercially available chemicals were used directly as received. 1H NMR was recorded at 400 MHz in Dimethylsulfoxide (DMSO-d6). 13C NMR was recorded at 400 MHz in DMSO-d6. Mass spectra was recorded on a Jeol SX 102=DA-6000 (10 kV) fast atom bombardment (FAB) mass spectrometer and IR spectra was recorded on a Nicolet 5700 F T—IR instrument as KBr discs.

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
O10.5699 (2)0.71184 (8)0.34374 (7)0.0409 (4)
O110.5487 (2)0.63066 (10)0.19274 (7)0.0541 (5)
O140.6120 (2)0.84884 (8)0.41311 (7)0.0515 (5)
O220.5085 (3)0.97085 (14)0.82793 (11)0.0869 (7)
O230.5615 (4)0.83031 (16)0.88337 (9)0.0860 (7)
N210.5394 (3)0.88318 (16)0.82255 (11)0.0613 (7)
C20.5811 (3)0.76190 (12)0.41836 (10)0.0384 (5)
C30.5552 (3)0.70612 (11)0.49641 (10)0.0371 (5)
C40.5162 (3)0.60920 (12)0.49082 (10)0.0404 (5)
C50.5066 (3)0.55829 (13)0.41241 (11)0.0418 (5)
C60.4682 (4)0.45725 (14)0.40574 (12)0.0552 (7)
C70.4586 (4)0.41549 (14)0.32849 (12)0.0600 (7)
C80.4848 (4)0.47095 (14)0.25537 (12)0.0555 (7)
C90.5232 (3)0.56989 (14)0.25975 (11)0.0440 (6)
C100.5335 (3)0.61330 (13)0.33952 (11)0.0385 (5)
C120.5377 (4)0.58696 (15)0.10978 (10)0.0560 (7)
C130.5582 (5)0.66749 (19)0.04725 (12)0.0751 (9)
C150.5625 (3)0.75681 (13)0.57930 (11)0.0378 (5)
C160.5182 (3)0.85604 (13)0.59012 (11)0.0431 (5)
C170.5132 (3)0.89769 (14)0.66921 (12)0.0489 (6)
C180.5499 (3)0.83947 (15)0.73796 (11)0.0484 (6)
C190.5985 (4)0.74317 (15)0.73029 (11)0.0528 (7)
C200.6066 (3)0.70218 (14)0.65155 (10)0.0486 (6)
H40.494800.574200.540100.0480*
H60.449800.419600.453800.0660*
H70.434100.348800.324000.0720*
H80.476200.440700.203100.0670*
H12A0.412700.554000.102500.0670*
H12B0.642100.539500.102500.0670*
H13A0.452400.713200.054200.1120*
H13B0.554500.64080−0.008500.1120*
H13C0.681100.700400.055800.1120*
H160.491700.894500.543300.0520*
H170.485500.963800.675800.0590*
H190.625800.705800.777700.0630*
H200.642000.636800.646000.0580*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0562 (8)0.0396 (7)0.0269 (6)0.0029 (6)−0.0021 (6)0.0005 (5)
O110.0836 (11)0.0500 (8)0.0286 (6)0.0015 (7)−0.0015 (6)−0.0034 (5)
O140.0842 (11)0.0360 (6)0.0344 (6)−0.0016 (6)−0.0087 (7)0.0027 (5)
O220.1200 (16)0.0747 (11)0.0659 (10)−0.0020 (11)0.0099 (11)−0.0370 (9)
O230.1136 (16)0.1095 (13)0.0350 (8)0.0045 (13)−0.0005 (9)−0.0103 (9)
N210.0599 (11)0.0818 (14)0.0423 (10)−0.0075 (10)0.0042 (9)−0.0213 (9)
C20.0450 (10)0.0401 (9)0.0301 (8)0.0039 (7)−0.0032 (8)−0.0012 (7)
C30.0418 (10)0.0411 (9)0.0285 (8)0.0045 (8)−0.0017 (8)−0.0005 (7)
C40.0491 (10)0.0430 (9)0.0291 (8)0.0027 (9)0.0004 (7)0.0012 (7)
C50.0506 (10)0.0424 (9)0.0325 (8)0.0024 (8)−0.0013 (8)−0.0007 (7)
C60.0810 (15)0.0430 (9)0.0417 (10)−0.0023 (10)0.0016 (11)0.0015 (8)
C70.0931 (17)0.0382 (10)0.0487 (10)−0.0053 (10)−0.0022 (12)−0.0052 (8)
C80.0799 (15)0.0470 (10)0.0397 (9)0.0034 (10)−0.0059 (10)−0.0128 (8)
C90.0552 (12)0.0485 (10)0.0282 (8)0.0061 (9)−0.0020 (8)−0.0017 (7)
C100.0433 (9)0.0383 (9)0.0339 (8)0.0044 (8)−0.0014 (8)−0.0014 (7)
C120.0765 (15)0.0636 (12)0.0279 (9)0.0073 (11)−0.0024 (9)−0.0081 (8)
C130.107 (2)0.0833 (15)0.0351 (11)−0.0015 (16)0.0019 (13)−0.0004 (10)
C150.0382 (9)0.0433 (9)0.0318 (8)0.0011 (7)−0.0010 (7)−0.0026 (7)
C160.0500 (10)0.0432 (9)0.0360 (9)−0.0011 (8)−0.0014 (8)−0.0033 (7)
C170.0528 (11)0.0435 (10)0.0504 (11)−0.0023 (9)0.0037 (10)−0.0108 (8)
C180.0473 (11)0.0645 (12)0.0334 (9)−0.0062 (10)0.0010 (8)−0.0138 (8)
C190.0649 (13)0.0621 (12)0.0314 (9)0.0026 (10)−0.0051 (9)−0.0008 (8)
C200.0651 (13)0.0475 (10)0.0333 (9)0.0055 (10)−0.0048 (9)−0.0014 (8)
Geometric parameters (Å, º) top
O1—C21.372 (2)C15—C161.401 (3)
O1—C101.372 (2)C15—C201.403 (2)
O11—C91.363 (2)C16—C171.382 (3)
O11—C121.451 (2)C17—C181.376 (3)
O14—C21.210 (2)C18—C191.363 (3)
O22—N211.220 (3)C19—C201.373 (2)
O23—N211.217 (3)C4—H40.9300
N21—C181.474 (3)C6—H60.9300
C2—C31.468 (2)C7—H70.9300
C3—C41.354 (2)C8—H80.9300
C3—C151.491 (2)C12—H12A0.9700
C4—C51.430 (2)C12—H12B0.9700
C5—C61.410 (3)C13—H13A0.9600
C5—C101.394 (3)C13—H13B0.9600
C6—C71.357 (3)C13—H13C0.9600
C7—C81.400 (3)C16—H160.9300
C8—C91.380 (3)C17—H170.9300
C9—C101.403 (3)C19—H190.9300
C12—C131.490 (3)C20—H200.9300
C2—O1—C10122.84 (13)N21—C18—C19119.02 (17)
C9—O11—C12117.00 (15)C17—C18—C19122.13 (17)
O22—N21—O23123.3 (2)C18—C19—C20119.05 (17)
O22—N21—C18118.08 (18)C15—C20—C19121.42 (18)
O23—N21—C18118.6 (2)C3—C4—H4119.00
O1—C2—O14116.10 (14)C5—C4—H4119.00
O1—C2—C3117.77 (14)C5—C6—H6120.00
O14—C2—C3126.14 (15)C7—C6—H6120.00
C2—C3—C4118.45 (14)C6—C7—H7119.00
C2—C3—C15120.19 (14)C8—C7—H7119.00
C4—C3—C15121.30 (15)C7—C8—H8120.00
C3—C4—C5122.85 (15)C9—C8—H8120.00
C4—C5—C6123.44 (16)O11—C12—H12A110.00
C4—C5—C10117.19 (16)O11—C12—H12B110.00
C6—C5—C10119.36 (16)C13—C12—H12A110.00
C5—C6—C7119.30 (18)C13—C12—H12B110.00
C6—C7—C8121.24 (18)H12A—C12—H12B109.00
C7—C8—C9120.88 (17)C12—C13—H13A109.00
O11—C9—C8125.63 (16)C12—C13—H13B109.00
O11—C9—C10116.32 (16)C12—C13—H13C109.00
C8—C9—C10118.04 (17)H13A—C13—H13B110.00
O1—C10—C5120.86 (15)H13A—C13—H13C109.00
O1—C10—C9117.97 (15)H13B—C13—H13C109.00
C5—C10—C9121.17 (17)C15—C16—H16119.00
O11—C12—C13107.35 (16)C17—C16—H16119.00
C3—C15—C16123.50 (16)C16—C17—H17121.00
C3—C15—C20118.97 (15)C18—C17—H17121.00
C16—C15—C20117.46 (16)C18—C19—H19120.00
C15—C16—C17121.10 (17)C20—C19—H19121.00
C16—C17—C18118.76 (18)C15—C20—H20119.00
N21—C18—C17118.84 (18)C19—C20—H20119.00
C10—O1—C2—O14−179.25 (17)C6—C5—C10—C9−0.1 (3)
C10—O1—C2—C30.8 (3)C4—C5—C10—C9−178.89 (19)
C2—O1—C10—C5−0.3 (3)C4—C5—C6—C7178.9 (2)
C2—O1—C10—C9179.35 (18)C10—C5—C6—C70.1 (4)
C12—O11—C9—C8−1.1 (3)C4—C5—C10—O10.8 (3)
C12—O11—C9—C10−179.77 (19)C5—C6—C7—C8−0.4 (4)
C9—O11—C12—C13176.8 (2)C6—C7—C8—C90.6 (4)
O23—N21—C18—C17176.1 (2)C7—C8—C9—C10−0.5 (4)
O22—N21—C18—C19175.2 (2)C7—C8—C9—O11−179.2 (2)
O22—N21—C18—C17−3.8 (3)O11—C9—C10—C5179.02 (18)
O23—N21—C18—C19−4.9 (3)C8—C9—C10—O1−179.4 (2)
O1—C2—C3—C4−1.9 (3)C8—C9—C10—C50.3 (3)
O1—C2—C3—C15−178.98 (17)O11—C9—C10—O1−0.7 (3)
O14—C2—C3—C151.1 (3)C3—C15—C16—C17175.17 (19)
O14—C2—C3—C4178.2 (2)C20—C15—C16—C17−1.7 (3)
C2—C3—C15—C20−157.80 (19)C3—C15—C20—C19−174.2 (2)
C2—C3—C15—C1625.4 (3)C16—C15—C20—C192.8 (3)
C2—C3—C4—C52.5 (3)C15—C16—C17—C18−0.9 (3)
C4—C3—C15—C16−151.6 (2)C16—C17—C18—N21−178.37 (19)
C4—C3—C15—C2025.2 (3)C16—C17—C18—C192.6 (3)
C15—C3—C4—C5179.53 (19)N21—C18—C19—C20179.4 (2)
C3—C4—C5—C6179.3 (2)C17—C18—C19—C20−1.6 (4)
C3—C4—C5—C10−1.9 (3)C18—C19—C20—C15−1.2 (4)
C6—C5—C10—O1179.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O22i0.932.533.453 (2)171
C8—H8···O14ii0.932.313.226 (2)166
C20—H20···O22i0.932.523.275 (3)138
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O22i0.932.533.453 (2)171
C8—H8···O14ii0.932.313.226 (2)166
C20—H20···O22i0.932.523.275 (3)138
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+1/2.
 

Acknowledgements

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

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ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o860-o861
https://doi.org/10.1107/S2056989015019325
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