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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 70| Part 2| February 2014| Page o176
doi:10.1107/S1600536814001123

7-Di­ethyl­amino-3-{(E)-4-[(E)-2-(pyridin-4-yl)ethen­yl]styr­yl}-2H-chromen-2-one

Li-Ping Zhoua and Ling-Liang Longa*

aFunctional Molecular Materials Research Centre, Scientific Research Academy & School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, Jiangsu 212013, People's Republic of China
*Correspondence e-mail: linglianglong@gmail.com

(Received 7 January 2014; accepted 16 January 2014; online 22 January 2014)

In the title coumarin derivative, C28H26N2O2, the coumarin unit is approximately planar, with a maximum deviation of 0.048 (3) Å. The central benzene ring is oriented at dihedral angles of 30.15 (14) and 10.51 (11)°, respectively, to the pyridine ring and coumarin ring system. In the crystal, weak C—H⋯O and C—H⋯N hydrogen bonds and weak C—H⋯π inter­actions link the mol­ecules into a three-dimensional supra­molecular architecture.

CCDC reference: 981709

Related literature

For applications of coumarin derivatives, see: Gong et al. (2012[Gong, Y., Zhang, X., Zhang, C., Luo, A., Fu, T., Tan, W., Shen, G. & Yu, R. (2012). Anal. Chem. 84, 10777-10784.]); Jones et al. (1985[Jones, G., Jackson, W. R., Choi, C. & Bergmark, W. R. (1985). J. Phys. Chem. 89, 294-300.]); Nemkovich et al. (1997[Nemkovich, N. A., Reis, H. & Baumann, W. (1997). J. Lumin. 71, 255-263.]); Jin et al. (2011[Jin, X., Uttamapinant, C. & Ting, A. Y. (2011). ChemBioChem, 12, 65-70.]); Helal et al. (2011[Helal, A., Rashid, M. H. O., Choi, C. & Kim, H. (2011). Tetrahedron, 67, 2794-2802.]).

[Scheme 1]

Experimental

Crystal data

  • C28H26N2O2

  • Mr = 422.51

  • Monoclinic, P 21 /n

  • a = 15.511 (3) Å

  • b = 8.4745 (17) Å

  • c = 16.882 (7) Å

  • β = 97.73 (3)°

  • V = 2198.9 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.27 × 0.25 × 0.23 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • 9607 measured reflections

  • 3931 independent reflections

  • 2993 reflections with I > 2σ(I)

  • Rint = 0.045
Refinement

  • R[F2 > 2σ(F2)] = 0.077

  • wR(F2) = 0.170

  • S = 1.13

  • 3931 reflections

  • 291 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the pyridine ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C21—H21⋯O1i 0.93 2.48 3.351 (4) 156
C25—H25A⋯N1ii 0.97 2.60 3.485 (4) 152
C25—H25B⋯O1i 0.97 2.56 3.433 (4) 150
C9—H9⋯Cg2iii 0.93 2.94 3.728 (4) 143
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [x-{\script{3\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 981709

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814001123/xu5763sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814001123/xu5763Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814001123/xu5763Isup3.cml

checkCIF report


Comment top

The coumarin derivatives are widely used fluorescence dye with favorable optical properties including high fluorescence quantum yield, superior photostability, and extended spectral range. These outstanding optical properties allow them to be potentially utilized in a wide range of areas such as ion sensing (Gong et al., 2012), laser dyes (Jones et al., 1985), nonlinear optical chromophores (Nemkovich et al., 1997), fluorescent labeling of biomaterials (Jin et al., 2011), and so on. In addition, previous studies have demonstrated that the optical properties of the coumarin dye could be improved by introducing conjugated group at the 3 position of the coumarin ring (Helal et al., 2011). These promoted us to develop large conjugated coumarin derevatives. Herein, the synthesis and crystal structure of title molecule are presented.

The analysis of title molecule shows that it crystallizes in the monoclinic space group P 21/n with four molecules in the unit cell. In the molecule, the C17—O1 bonds, C6—C7 bonds and C14—C15 bonds show typical double-bond character (Figure 1, Table 1). The length of the C6—C7 bonds [1.333 (4) Å] compares favorably to that of the analogous C14—C15 bond [1.317 (4) Å]. On the other hand, the C17—O1 bond length [1.212 (3) Å] is shorter than that C17—O2 [1.392 (3) Å]. The coumarin ring, phenyl ring, and pyridine ring were connected by the two C—C double bonds (C6—C7 bond and C14—C15 bond), which make the three rings in good conjugation. In addition, the dihedral angles between the mean planes of the pyridine ring and the phenyl ring, the phenyl ring and the coumarin ring are 30.203 (8)°, 9.538 (7)°, respectively (Figure 2). The crystal structure of the title molecule is characterized by inter­molecular C—H···O and C—H···N hydrogen bonding (Figures 3 and 4, Table 1). The inter­molecular hydrogen-bonding scheme features a bifurcated inter­action to atom O1 and an R22 (7) and R22 (12) graph sets, as shown in Figure 3. The inter­molecular hydrogen-bonding scheme features an inter­action to atom N1, as shown in Figure 4. The crystal packing diagram are the fundamental linking units in the formation of a supra­molecular structure with inter­molecular C—H···O and C—H···N hydrogen-bonds, as shown in Figure 5.

Synthesis and crystallization top

1N sodium hydroxide solution (1ml) was added dropwise to a solution of 7-di­ethyl­amino­coumarin-3-carbaldehyde (0.391g, 1.596mmol) and (1,4-phenyl­enebis(methyl­ene))bis­(tri­phenyl­phospho­nium) chloride (1g, 1.596mmol) in di­chloro­methane (20ml). The reaction mixture was stirred overnight at room temperature. After removal of the solvent under reduced pressure, the resulting mixture was purified by column chromatography on silica gel (di­chloro­methane: petroleum ether = 3: 7, v/v) to afford a yellow solid. Then, 1N sodium hydroxide solution (1ml) was added dropwise to the resulting yellow solid (0.5g, 0.84mmol) and isonicotinaldehyde (0.09g, 0.84mmol) in di­chloro­methane (20ml). The solution was stirred for 8 hours at room temperature. After removal of the solvent under reduced pressure, the crude product was purified by column chromatography on silica gel (di­chloro­methane: petroleum ether = 2: 3, v/v) to afford the title compound as red solid (184mg, yield 52%). Mp 265-266oC. The crystal appropriate for X-ray data collection was obtained from methanol- di­chloro­methane solution at room temperature after about a week.

Refinement top

H atoms were positioned geometrically and refined with riding model, with Uiso = 1.2Ueq or 1.5Ueq for all H atoms. The C—H bond are 0.93 (pyridyl, aromatic), 0.96 (methyl), or 0.97Å (methyl­ene).

Related literature top

For applications of coumarin derivatives, see: Gong et al. (2012); Jones et al. (1985); Nemkovich et al. (1997); Jin et al. (2011); Helal et al. (2011).

Structure description top

The coumarin derivatives are widely used fluorescence dye with favorable optical properties including high fluorescence quantum yield, superior photostability, and extended spectral range. These outstanding optical properties allow them to be potentially utilized in a wide range of areas such as ion sensing (Gong et al., 2012), laser dyes (Jones et al., 1985), nonlinear optical chromophores (Nemkovich et al., 1997), fluorescent labeling of biomaterials (Jin et al., 2011), and so on. In addition, previous studies have demonstrated that the optical properties of the coumarin dye could be improved by introducing conjugated group at the 3 position of the coumarin ring (Helal et al., 2011). These promoted us to develop large conjugated coumarin derevatives. Herein, the synthesis and crystal structure of title molecule are presented.

The analysis of title molecule shows that it crystallizes in the monoclinic space group P 21/n with four molecules in the unit cell. In the molecule, the C17—O1 bonds, C6—C7 bonds and C14—C15 bonds show typical double-bond character (Figure 1, Table 1). The length of the C6—C7 bonds [1.333 (4) Å] compares favorably to that of the analogous C14—C15 bond [1.317 (4) Å]. On the other hand, the C17—O1 bond length [1.212 (3) Å] is shorter than that C17—O2 [1.392 (3) Å]. The coumarin ring, phenyl ring, and pyridine ring were connected by the two C—C double bonds (C6—C7 bond and C14—C15 bond), which make the three rings in good conjugation. In addition, the dihedral angles between the mean planes of the pyridine ring and the phenyl ring, the phenyl ring and the coumarin ring are 30.203 (8)°, 9.538 (7)°, respectively (Figure 2). The crystal structure of the title molecule is characterized by inter­molecular C—H···O and C—H···N hydrogen bonding (Figures 3 and 4, Table 1). The inter­molecular hydrogen-bonding scheme features a bifurcated inter­action to atom O1 and an R22 (7) and R22 (12) graph sets, as shown in Figure 3. The inter­molecular hydrogen-bonding scheme features an inter­action to atom N1, as shown in Figure 4. The crystal packing diagram are the fundamental linking units in the formation of a supra­molecular structure with inter­molecular C—H···O and C—H···N hydrogen-bonds, as shown in Figure 5.

For applications of coumarin derivatives, see: Gong et al. (2012); Jones et al. (1985); Nemkovich et al. (1997); Jin et al. (2011); Helal et al. (2011).

Synthesis and crystallization top

1N sodium hydroxide solution (1ml) was added dropwise to a solution of 7-di­ethyl­amino­coumarin-3-carbaldehyde (0.391g, 1.596mmol) and (1,4-phenyl­enebis(methyl­ene))bis­(tri­phenyl­phospho­nium) chloride (1g, 1.596mmol) in di­chloro­methane (20ml). The reaction mixture was stirred overnight at room temperature. After removal of the solvent under reduced pressure, the resulting mixture was purified by column chromatography on silica gel (di­chloro­methane: petroleum ether = 3: 7, v/v) to afford a yellow solid. Then, 1N sodium hydroxide solution (1ml) was added dropwise to the resulting yellow solid (0.5g, 0.84mmol) and isonicotinaldehyde (0.09g, 0.84mmol) in di­chloro­methane (20ml). The solution was stirred for 8 hours at room temperature. After removal of the solvent under reduced pressure, the crude product was purified by column chromatography on silica gel (di­chloro­methane: petroleum ether = 2: 3, v/v) to afford the title compound as red solid (184mg, yield 52%). Mp 265-266oC. The crystal appropriate for X-ray data collection was obtained from methanol- di­chloro­methane solution at room temperature after about a week.

Refinement details top

H atoms were positioned geometrically and refined with riding model, with Uiso = 1.2Ueq or 1.5Ueq for all H atoms. The C—H bond are 0.93 (pyridyl, aromatic), 0.96 (methyl), or 0.97Å (methyl­ene).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of title molecule, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The dihedral angles (°) between adjacent planes. The pink, yellow, and blue planes represent pyridine ring, the benzene ring, and the coumarin ring.
[Figure 3] Fig. 3. A view of the C—H···O hydrogen-bonded ring and bifurcated nature of atom O2. Hydrogen-bond interactions are shown with dashed lines.
[Figure 4] Fig. 4. A view of the C—H···N hydrogen-bonds of atom N2. Hydrogen-bond interactions are shown with dashed lines.
[Figure 5] Fig. 5. The crystal packing of title molecule, viewed along the b axis. C—H···O and C—H···N hydrogen bonds are shown as dashed lines (see Table 1 for details).
7-Diethylamino-3-{(E)-4-[(E)-2-(pyridin-4-yl)ethenyl]styryl}-2H-chromen-2-one top
Crystal data top
C28H26N2O2F(000) = 896
Mr = 422.51Dx = 1.276 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9607 reflections
a = 15.511 (3) Åθ = 3.5–25.5°
b = 8.4745 (17) ŵ = 0.08 mm−1
c = 16.882 (7) ÅT = 293 K
β = 97.73 (3)°Block, pink
V = 2198.9 (11) Å30.27 × 0.25 × 0.23 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2993 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
Graphite monochromatorθmax = 25.2°, θmin = 3.6°
phi and ω scansh = −16→18
9607 measured reflectionsk = −10→8
3931 independent reflectionsl = −18→20
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)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.054P)2 + 1.2201P]
where P = (Fo2 + 2Fc2)/3
3931 reflections(Δ/σ)max = 0.004
291 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C28H26N2O2V = 2198.9 (11) Å3
Mr = 422.51Z = 4
Monoclinic, P21/nMo Kα radiation
a = 15.511 (3) ŵ = 0.08 mm−1
b = 8.4745 (17) ÅT = 293 K
c = 16.882 (7) Å0.27 × 0.25 × 0.23 mm
β = 97.73 (3)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2993 reflections with I > 2σ(I)
9607 measured reflectionsRint = 0.045
3931 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0770 restraints
wR(F2) = 0.170H-atom parameters constrained
S = 1.13Δρmax = 0.28 e Å−3
3931 reflectionsΔρmin = −0.21 e Å−3
291 parameters
Special details top

Experimental. 1H NMR (400MHz, CDCl3) δ (ppm): 8.60 (d, J = 6.0 Hz, 2H), 7.72 (s, 1H), 7.53 (m, 7H), 7.41(d, J = 16.0 Hz, 1H), 7.33 (d, J = 9.0 Hz, 1H), 7.19 (d, J = 16.4 Hz, 1H), 7.09 (d, J = 16.4 Hz, 1H), 6.64 (dd, J1 = 2.4 Hz, J2 = 8.8 Hz, 1H), 6.54 (d, J = 2.4 Hz, 1H), 3.48 (q, J = 7.2 Hz, 4H), 1.27 (t, J = 7.2 Hz, 6H). ESI-MS (m/z): 423.3 [M+1]+. Anal. calcd for C28H26N2O2: C 79.59, H 6.20, N 6.63; found C 79.34, H 6.23, N 6.61.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
N11.47594 (15)0.3672 (3)0.89342 (16)0.0470 (7)
N20.22420 (13)0.3446 (3)0.48620 (14)0.0365 (6)
O10.65839 (12)0.1130 (3)0.54400 (15)0.0588 (7)
O20.52260 (11)0.1909 (2)0.53258 (13)0.0415 (5)
C11.40807 (18)0.4019 (4)0.93132 (19)0.0498 (8)
H11.41960.43680.98390.060*
C21.32252 (18)0.3898 (4)0.89825 (19)0.0457 (8)
H21.27830.41470.92830.055*
C31.30236 (17)0.3397 (3)0.81916 (17)0.0362 (7)
C41.37250 (17)0.3025 (3)0.77916 (19)0.0411 (7)
H41.36310.26760.72650.049*
C51.45611 (18)0.3177 (4)0.8182 (2)0.0461 (8)
H51.50180.29160.79010.055*
C61.21301 (17)0.3227 (3)0.77934 (18)0.0383 (7)
H61.20520.26390.73240.046*
C71.14170 (17)0.3832 (3)0.80373 (17)0.0372 (7)
H71.14970.44750.84870.045*
C81.05196 (17)0.3579 (3)0.76635 (17)0.0359 (7)
C91.02959 (17)0.2394 (4)0.70924 (17)0.0386 (7)
H91.07310.17580.69340.046*
C100.94475 (17)0.2154 (3)0.67630 (17)0.0385 (7)
H100.93210.13480.63920.046*
C110.87729 (17)0.3078 (3)0.69667 (17)0.0369 (7)
C120.89826 (17)0.4242 (4)0.75531 (18)0.0418 (8)
H120.85450.48640.77160.050*
C130.98422 (17)0.4470 (4)0.78924 (19)0.0430 (7)
H130.99670.52400.82830.052*
C140.78861 (18)0.2774 (3)0.65598 (18)0.0404 (7)
H140.78060.18600.62540.048*
C150.71960 (18)0.3667 (3)0.65861 (18)0.0404 (7)
H150.72850.45680.69010.048*
C160.63081 (17)0.3435 (3)0.61866 (17)0.0353 (7)
C170.60931 (17)0.2112 (3)0.5649 (2)0.0409 (7)
C180.45869 (16)0.2969 (3)0.54637 (17)0.0336 (7)
C190.48051 (17)0.4303 (3)0.59359 (16)0.0342 (7)
C200.56747 (17)0.4488 (3)0.62915 (17)0.0372 (7)
H200.58200.53680.66110.045*
C210.37542 (16)0.2645 (3)0.51058 (17)0.0342 (7)
H210.36390.17340.48030.041*
C220.30769 (17)0.3713 (3)0.52046 (16)0.0339 (7)
C230.32947 (18)0.5082 (4)0.56701 (17)0.0400 (7)
H230.28620.58070.57430.048*
C240.41301 (18)0.5355 (4)0.60136 (17)0.0417 (7)
H240.42530.62730.63090.050*
C250.19833 (18)0.1976 (3)0.44438 (18)0.0395 (7)
H25A0.13840.17440.45080.047*
H25B0.23420.11240.46880.047*
C260.15537 (17)0.4615 (4)0.48859 (17)0.0393 (7)
H26A0.11340.45100.44080.047*
H26B0.18050.56630.48840.047*
C270.2064 (2)0.2034 (4)0.35653 (19)0.0475 (8)
H27A0.17150.28830.33200.071*
H27B0.18670.10540.33200.071*
H27C0.26610.22030.34970.071*
C280.1087 (2)0.4444 (5)0.56134 (19)0.0551 (9)
H28A0.08330.34110.56170.083*
H28B0.06380.52270.55960.083*
H28C0.14950.45860.60890.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0280 (13)0.0560 (17)0.0546 (17)−0.0014 (12)−0.0031 (12)0.0004 (14)
N20.0246 (12)0.0407 (14)0.0425 (14)0.0028 (10)−0.0018 (10)0.0017 (11)
O10.0295 (11)0.0415 (12)0.101 (2)0.0045 (10)−0.0078 (12)−0.0150 (13)
O20.0244 (10)0.0315 (10)0.0654 (14)0.0001 (8)−0.0053 (9)−0.0033 (10)
C10.0315 (16)0.070 (2)0.0445 (19)−0.0033 (16)−0.0056 (14)−0.0094 (17)
C20.0290 (15)0.060 (2)0.0471 (19)−0.0009 (15)0.0003 (13)−0.0041 (16)
C30.0280 (14)0.0391 (16)0.0396 (17)−0.0045 (12)−0.0025 (12)0.0014 (13)
C40.0333 (16)0.0456 (17)0.0434 (18)−0.0023 (14)0.0012 (13)−0.0022 (15)
C50.0284 (15)0.054 (2)0.055 (2)0.0012 (14)0.0033 (14)−0.0022 (17)
C60.0306 (15)0.0446 (17)0.0378 (17)−0.0034 (13)−0.0018 (13)0.0003 (14)
C70.0282 (14)0.0413 (17)0.0399 (17)−0.0038 (13)−0.0037 (12)0.0026 (13)
C80.0279 (14)0.0412 (16)0.0372 (17)−0.0009 (13)−0.0003 (12)0.0106 (13)
C90.0251 (14)0.0488 (18)0.0407 (17)−0.0015 (13)−0.0006 (12)0.0032 (14)
C100.0340 (15)0.0440 (17)0.0358 (17)−0.0020 (14)−0.0015 (13)0.0039 (13)
C110.0305 (15)0.0434 (17)0.0351 (16)−0.0067 (13)−0.0014 (12)0.0109 (14)
C120.0260 (14)0.0458 (18)0.054 (2)0.0030 (13)0.0052 (13)0.0096 (15)
C130.0323 (15)0.0440 (17)0.0508 (19)−0.0018 (14)−0.0015 (14)0.0001 (15)
C140.0364 (16)0.0374 (16)0.0467 (18)−0.0047 (14)0.0030 (14)0.0050 (14)
C150.0360 (16)0.0392 (17)0.0450 (18)−0.0033 (14)0.0022 (14)0.0058 (14)
C160.0277 (14)0.0407 (16)0.0357 (16)−0.0067 (13)−0.0022 (12)0.0071 (13)
C170.0223 (14)0.0345 (16)0.064 (2)0.0040 (13)−0.0026 (14)0.0067 (15)
C180.0237 (14)0.0319 (15)0.0438 (17)0.0016 (12)−0.0013 (12)0.0048 (13)
C190.0298 (14)0.0383 (16)0.0332 (16)−0.0022 (13)−0.0004 (12)0.0003 (13)
C200.0322 (15)0.0419 (17)0.0360 (16)−0.0060 (13)−0.0007 (12)−0.0046 (13)
C210.0263 (14)0.0293 (14)0.0452 (17)−0.0011 (12)−0.0017 (12)−0.0004 (12)
C220.0280 (14)0.0425 (16)0.0307 (16)0.0013 (13)0.0024 (12)0.0027 (12)
C230.0328 (15)0.0473 (18)0.0391 (17)0.0055 (14)0.0012 (13)−0.0076 (14)
C240.0404 (17)0.0456 (18)0.0382 (17)−0.0020 (15)0.0022 (13)−0.0134 (14)
C250.0267 (14)0.0379 (16)0.0518 (19)−0.0036 (13)−0.0022 (13)0.0041 (14)
C260.0275 (14)0.0515 (18)0.0383 (17)0.0093 (14)0.0022 (12)0.0031 (14)
C270.0424 (17)0.0476 (19)0.051 (2)−0.0014 (15)0.0002 (15)−0.0026 (15)
C280.0389 (17)0.081 (3)0.047 (2)0.0071 (17)0.0121 (15)0.0084 (18)
Geometric parameters (Å, º) top
N1—C51.334 (4)C13—H130.9300
N1—C11.336 (4)C14—C151.317 (4)
N2—C221.364 (3)C14—H140.9300
N2—C251.461 (4)C15—C161.463 (4)
N2—C261.461 (3)C15—H150.9300
O1—C171.212 (3)C16—C201.356 (4)
O2—C181.381 (3)C16—C171.453 (4)
O2—C171.392 (3)C18—C211.378 (4)
C1—C21.372 (4)C18—C191.398 (4)
C1—H10.9300C19—C241.395 (4)
C2—C31.396 (4)C19—C201.409 (4)
C2—H20.9300C20—H200.9300
C3—C41.392 (4)C21—C221.413 (4)
C3—C61.464 (4)C21—H210.9300
C4—C51.379 (4)C22—C231.417 (4)
C4—H40.9300C23—C241.366 (4)
C5—H50.9300C23—H230.9300
C6—C71.333 (4)C24—H240.9300
C6—H60.9300C25—C271.506 (4)
C7—C81.465 (4)C25—H25A0.9700
C7—H70.9300C25—H25B0.9700
C8—C131.390 (4)C26—C281.514 (4)
C8—C91.403 (4)C26—H26A0.9700
C9—C101.373 (4)C26—H26B0.9700
C9—H90.9300C27—H27A0.9600
C10—C111.387 (4)C27—H27B0.9600
C10—H100.9300C27—H27C0.9600
C11—C121.404 (4)C28—H28A0.9600
C11—C141.475 (4)C28—H28B0.9600
C12—C131.392 (4)C28—H28C0.9600
C12—H120.9300
C5—N1—C1115.4 (3)C20—C16—C15120.3 (3)
C22—N2—C25122.0 (2)C17—C16—C15121.0 (3)
C22—N2—C26122.1 (2)O1—C17—O2114.4 (3)
C25—N2—C26115.9 (2)O1—C17—C16127.7 (3)
C18—O2—C17122.1 (2)O2—C17—C16117.9 (2)
N1—C1—C2124.7 (3)C21—C18—O2116.6 (2)
N1—C1—H1117.6C21—C18—C19123.5 (3)
C2—C1—H1117.6O2—C18—C19119.9 (2)
C1—C2—C3119.5 (3)C24—C19—C18116.3 (2)
C1—C2—H2120.3C24—C19—C20125.2 (3)
C3—C2—H2120.3C18—C19—C20118.5 (3)
C4—C3—C2116.3 (3)C16—C20—C19122.7 (3)
C4—C3—C6120.6 (3)C16—C20—H20118.7
C2—C3—C6123.1 (3)C19—C20—H20118.7
C5—C4—C3119.6 (3)C18—C21—C22119.2 (3)
C5—C4—H4120.2C18—C21—H21120.4
C3—C4—H4120.2C22—C21—H21120.4
N1—C5—C4124.4 (3)N2—C22—C21121.4 (3)
N1—C5—H5117.8N2—C22—C23120.9 (2)
C4—C5—H5117.8C21—C22—C23117.7 (2)
C7—C6—C3126.4 (3)C24—C23—C22121.1 (3)
C7—C6—H6116.8C24—C23—H23119.5
C3—C6—H6116.8C22—C23—H23119.5
C6—C7—C8126.2 (3)C23—C24—C19122.2 (3)
C6—C7—H7116.9C23—C24—H24118.9
C8—C7—H7116.9C19—C24—H24118.9
C13—C8—C9117.0 (3)N2—C25—C27113.2 (2)
C13—C8—C7120.7 (3)N2—C25—H25A108.9
C9—C8—C7122.3 (3)C27—C25—H25A108.9
C10—C9—C8121.3 (3)N2—C25—H25B108.9
C10—C9—H9119.4C27—C25—H25B108.9
C8—C9—H9119.4H25A—C25—H25B107.7
C9—C10—C11122.0 (3)N2—C26—C28112.9 (2)
C9—C10—H10119.0N2—C26—H26A109.0
C11—C10—H10119.0C28—C26—H26A109.0
C10—C11—C12117.4 (3)N2—C26—H26B109.0
C10—C11—C14118.2 (3)C28—C26—H26B109.0
C12—C11—C14124.3 (3)H26A—C26—H26B107.8
C13—C12—C11120.4 (3)C25—C27—H27A109.5
C13—C12—H12119.8C25—C27—H27B109.5
C11—C12—H12119.8H27A—C27—H27B109.5
C8—C13—C12121.9 (3)C25—C27—H27C109.5
C8—C13—H13119.1H27A—C27—H27C109.5
C12—C13—H13119.1H27B—C27—H27C109.5
C15—C14—C11126.5 (3)C26—C28—H28A109.5
C15—C14—H14116.7C26—C28—H28B109.5
C11—C14—H14116.7H28A—C28—H28B109.5
C14—C15—C16128.8 (3)C26—C28—H28C109.5
C14—C15—H15115.6H28A—C28—H28C109.5
C16—C15—H15115.6H28B—C28—H28C109.5
C20—C16—C17118.7 (2)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the pyridine ring.
D—H···AD—HH···AD···AD—H···A
C21—H21···O1i0.932.483.351 (4)156
C25—H25A···N1ii0.972.603.485 (4)152
C25—H25B···O1i0.972.563.433 (4)150
C9—H9···Cg2iii0.932.943.728 (4)143
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−3/2, −y+1/2, z−1/2; (iii) −x+5/2, y−1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the pyridine ring.
D—H···AD—HH···AD···AD—H···A
C21—H21···O1i0.932.483.351 (4)156
C25—H25A···N1ii0.972.603.485 (4)152
C25—H25B···O1i0.972.563.433 (4)150
C9—H9···Cg2iii0.932.943.728 (4)143
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−3/2, −y+1/2, z−1/2; (iii) −x+5/2, y−1/2, −z+3/2.
 

Acknowledgements

The work was supported by National Natural Science Foundation of China (21202063), the Natural Science Foundation of Jiangsu Province (BK2012281), the China Postdoctoral Science Foundation (2012M511200) and the Research Foundation of Jiangsu University (11JDG078).

References

First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationGong, Y., Zhang, X., Zhang, C., Luo, A., Fu, T., Tan, W., Shen, G. & Yu, R. (2012). Anal. Chem. 84, 10777–10784.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationHelal, A., Rashid, M. H. O., Choi, C. & Kim, H. (2011). Tetrahedron, 67, 2794–2802.  Web of Science CrossRef CAS Google Scholar
 First citationJin, X., Uttamapinant, C. & Ting, A. Y. (2011). ChemBioChem, 12, 65–70.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationJones, G., Jackson, W. R., Choi, C. & Bergmark, W. R. (1985). J. Phys. Chem. 89, 294–300.  CrossRef CAS Web of Science Google Scholar
 First citationNemkovich, N. A., Reis, H. & Baumann, W. (1997). J. Lumin. 71, 255–263.  CrossRef CAS Web of Science Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 70| Part 2| February 2014| Page o176
doi:10.1107/S1600536814001123
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