organic compounds
7-Diethylamino-3-{(E)-4-[(E)-2-(pyridin-4-yl)ethenyl]styryl}-2H-chromen-2-one
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
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); Jones et al. (1985); Nemkovich et al. (1997); Jin et al. (2011); Helal et al. (2011).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 981709
10.1107/S1600536814001123/xu5763sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001123/xu5763Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001123/xu5763Isup3.cml
The coumarin derivatives are widely used fluorescence dye with favorable optical properties including high fluorescence
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 of title molecule are presented.The analysis of title molecule shows that it crystallizes in the monoclinic
P 21/n with four molecules in the 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 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 5.1N 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
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 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.The coumarin derivatives are widely used fluorescence dye with favorable optical properties including high fluorescence
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 of title molecule are presented.The analysis of title molecule shows that it crystallizes in the monoclinic
P 21/n with four molecules in the 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 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).
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
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 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. detailsH 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).
Data collection: APEX2 (Bruker, 2008); cell
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).Fig. 1. The structure of title molecule, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. The dihedral angles (°) between adjacent planes. The pink, yellow, and blue planes represent pyridine ring, the benzene ring, and the coumarin ring. | |
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. | |
Fig. 4. A view of the C—H···N hydrogen-bonds of atom N2. Hydrogen-bond interactions are shown with dashed lines. | |
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). |
C28H26N2O2 | F(000) = 896 |
Mr = 422.51 | Dx = 1.276 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9607 reflections |
a = 15.511 (3) Å | θ = 3.5–25.5° |
b = 8.4745 (17) Å | µ = 0.08 mm−1 |
c = 16.882 (7) Å | T = 293 K |
β = 97.73 (3)° | Block, pink |
V = 2198.9 (11) Å3 | 0.27 × 0.25 × 0.23 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 2993 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 25.2°, θmin = 3.6° |
phi and ω scans | h = −16→18 |
9607 measured reflections | k = −10→8 |
3931 independent reflections | l = −18→20 |
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)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-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 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C28H26N2O2 | V = 2198.9 (11) Å3 |
Mr = 422.51 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.511 (3) Å | µ = 0.08 mm−1 |
b = 8.4745 (17) Å | T = 293 K |
c = 16.882 (7) Å | 0.27 × 0.25 × 0.23 mm |
β = 97.73 (3)° |
Bruker APEXII CCD area-detector diffractometer | 2993 reflections with I > 2σ(I) |
9607 measured reflections | Rint = 0.045 |
3931 independent reflections |
R[F2 > 2σ(F2)] = 0.077 | 0 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.28 e Å−3 |
3931 reflections | Δρmin = −0.21 e Å−3 |
291 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 1.47594 (15) | 0.3672 (3) | 0.89342 (16) | 0.0470 (7) | |
N2 | 0.22420 (13) | 0.3446 (3) | 0.48620 (14) | 0.0365 (6) | |
O1 | 0.65839 (12) | 0.1130 (3) | 0.54400 (15) | 0.0588 (7) | |
O2 | 0.52260 (11) | 0.1909 (2) | 0.53258 (13) | 0.0415 (5) | |
C1 | 1.40807 (18) | 0.4019 (4) | 0.93132 (19) | 0.0498 (8) | |
H1 | 1.4196 | 0.4368 | 0.9839 | 0.060* | |
C2 | 1.32252 (18) | 0.3898 (4) | 0.89825 (19) | 0.0457 (8) | |
H2 | 1.2783 | 0.4147 | 0.9283 | 0.055* | |
C3 | 1.30236 (17) | 0.3397 (3) | 0.81916 (17) | 0.0362 (7) | |
C4 | 1.37250 (17) | 0.3025 (3) | 0.77916 (19) | 0.0411 (7) | |
H4 | 1.3631 | 0.2676 | 0.7265 | 0.049* | |
C5 | 1.45611 (18) | 0.3177 (4) | 0.8182 (2) | 0.0461 (8) | |
H5 | 1.5018 | 0.2916 | 0.7901 | 0.055* | |
C6 | 1.21301 (17) | 0.3227 (3) | 0.77934 (18) | 0.0383 (7) | |
H6 | 1.2052 | 0.2639 | 0.7324 | 0.046* | |
C7 | 1.14170 (17) | 0.3832 (3) | 0.80373 (17) | 0.0372 (7) | |
H7 | 1.1497 | 0.4475 | 0.8487 | 0.045* | |
C8 | 1.05196 (17) | 0.3579 (3) | 0.76635 (17) | 0.0359 (7) | |
C9 | 1.02959 (17) | 0.2394 (4) | 0.70924 (17) | 0.0386 (7) | |
H9 | 1.0731 | 0.1758 | 0.6934 | 0.046* | |
C10 | 0.94475 (17) | 0.2154 (3) | 0.67630 (17) | 0.0385 (7) | |
H10 | 0.9321 | 0.1348 | 0.6392 | 0.046* | |
C11 | 0.87729 (17) | 0.3078 (3) | 0.69667 (17) | 0.0369 (7) | |
C12 | 0.89826 (17) | 0.4242 (4) | 0.75531 (18) | 0.0418 (8) | |
H12 | 0.8545 | 0.4864 | 0.7716 | 0.050* | |
C13 | 0.98422 (17) | 0.4470 (4) | 0.78924 (19) | 0.0430 (7) | |
H13 | 0.9967 | 0.5240 | 0.8283 | 0.052* | |
C14 | 0.78861 (18) | 0.2774 (3) | 0.65598 (18) | 0.0404 (7) | |
H14 | 0.7806 | 0.1860 | 0.6254 | 0.048* | |
C15 | 0.71960 (18) | 0.3667 (3) | 0.65861 (18) | 0.0404 (7) | |
H15 | 0.7285 | 0.4568 | 0.6901 | 0.048* | |
C16 | 0.63081 (17) | 0.3435 (3) | 0.61866 (17) | 0.0353 (7) | |
C17 | 0.60931 (17) | 0.2112 (3) | 0.5649 (2) | 0.0409 (7) | |
C18 | 0.45869 (16) | 0.2969 (3) | 0.54637 (17) | 0.0336 (7) | |
C19 | 0.48051 (17) | 0.4303 (3) | 0.59359 (16) | 0.0342 (7) | |
C20 | 0.56747 (17) | 0.4488 (3) | 0.62915 (17) | 0.0372 (7) | |
H20 | 0.5820 | 0.5368 | 0.6611 | 0.045* | |
C21 | 0.37542 (16) | 0.2645 (3) | 0.51058 (17) | 0.0342 (7) | |
H21 | 0.3639 | 0.1734 | 0.4803 | 0.041* | |
C22 | 0.30769 (17) | 0.3713 (3) | 0.52046 (16) | 0.0339 (7) | |
C23 | 0.32947 (18) | 0.5082 (4) | 0.56701 (17) | 0.0400 (7) | |
H23 | 0.2862 | 0.5807 | 0.5743 | 0.048* | |
C24 | 0.41301 (18) | 0.5355 (4) | 0.60136 (17) | 0.0417 (7) | |
H24 | 0.4253 | 0.6273 | 0.6309 | 0.050* | |
C25 | 0.19833 (18) | 0.1976 (3) | 0.44438 (18) | 0.0395 (7) | |
H25A | 0.1384 | 0.1744 | 0.4508 | 0.047* | |
H25B | 0.2342 | 0.1124 | 0.4688 | 0.047* | |
C26 | 0.15537 (17) | 0.4615 (4) | 0.48859 (17) | 0.0393 (7) | |
H26A | 0.1134 | 0.4510 | 0.4408 | 0.047* | |
H26B | 0.1805 | 0.5663 | 0.4884 | 0.047* | |
C27 | 0.2064 (2) | 0.2034 (4) | 0.35653 (19) | 0.0475 (8) | |
H27A | 0.1715 | 0.2883 | 0.3320 | 0.071* | |
H27B | 0.1867 | 0.1054 | 0.3320 | 0.071* | |
H27C | 0.2661 | 0.2203 | 0.3497 | 0.071* | |
C28 | 0.1087 (2) | 0.4444 (5) | 0.56134 (19) | 0.0551 (9) | |
H28A | 0.0833 | 0.3411 | 0.5617 | 0.083* | |
H28B | 0.0638 | 0.5227 | 0.5596 | 0.083* | |
H28C | 0.1495 | 0.4586 | 0.6089 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0280 (13) | 0.0560 (17) | 0.0546 (17) | −0.0014 (12) | −0.0031 (12) | 0.0004 (14) |
N2 | 0.0246 (12) | 0.0407 (14) | 0.0425 (14) | 0.0028 (10) | −0.0018 (10) | 0.0017 (11) |
O1 | 0.0295 (11) | 0.0415 (12) | 0.101 (2) | 0.0045 (10) | −0.0078 (12) | −0.0150 (13) |
O2 | 0.0244 (10) | 0.0315 (10) | 0.0654 (14) | 0.0001 (8) | −0.0053 (9) | −0.0033 (10) |
C1 | 0.0315 (16) | 0.070 (2) | 0.0445 (19) | −0.0033 (16) | −0.0056 (14) | −0.0094 (17) |
C2 | 0.0290 (15) | 0.060 (2) | 0.0471 (19) | −0.0009 (15) | 0.0003 (13) | −0.0041 (16) |
C3 | 0.0280 (14) | 0.0391 (16) | 0.0396 (17) | −0.0045 (12) | −0.0025 (12) | 0.0014 (13) |
C4 | 0.0333 (16) | 0.0456 (17) | 0.0434 (18) | −0.0023 (14) | 0.0012 (13) | −0.0022 (15) |
C5 | 0.0284 (15) | 0.054 (2) | 0.055 (2) | 0.0012 (14) | 0.0033 (14) | −0.0022 (17) |
C6 | 0.0306 (15) | 0.0446 (17) | 0.0378 (17) | −0.0034 (13) | −0.0018 (13) | 0.0003 (14) |
C7 | 0.0282 (14) | 0.0413 (17) | 0.0399 (17) | −0.0038 (13) | −0.0037 (12) | 0.0026 (13) |
C8 | 0.0279 (14) | 0.0412 (16) | 0.0372 (17) | −0.0009 (13) | −0.0003 (12) | 0.0106 (13) |
C9 | 0.0251 (14) | 0.0488 (18) | 0.0407 (17) | −0.0015 (13) | −0.0006 (12) | 0.0032 (14) |
C10 | 0.0340 (15) | 0.0440 (17) | 0.0358 (17) | −0.0020 (14) | −0.0015 (13) | 0.0039 (13) |
C11 | 0.0305 (15) | 0.0434 (17) | 0.0351 (16) | −0.0067 (13) | −0.0014 (12) | 0.0109 (14) |
C12 | 0.0260 (14) | 0.0458 (18) | 0.054 (2) | 0.0030 (13) | 0.0052 (13) | 0.0096 (15) |
C13 | 0.0323 (15) | 0.0440 (17) | 0.0508 (19) | −0.0018 (14) | −0.0015 (14) | 0.0001 (15) |
C14 | 0.0364 (16) | 0.0374 (16) | 0.0467 (18) | −0.0047 (14) | 0.0030 (14) | 0.0050 (14) |
C15 | 0.0360 (16) | 0.0392 (17) | 0.0450 (18) | −0.0033 (14) | 0.0022 (14) | 0.0058 (14) |
C16 | 0.0277 (14) | 0.0407 (16) | 0.0357 (16) | −0.0067 (13) | −0.0022 (12) | 0.0071 (13) |
C17 | 0.0223 (14) | 0.0345 (16) | 0.064 (2) | 0.0040 (13) | −0.0026 (14) | 0.0067 (15) |
C18 | 0.0237 (14) | 0.0319 (15) | 0.0438 (17) | 0.0016 (12) | −0.0013 (12) | 0.0048 (13) |
C19 | 0.0298 (14) | 0.0383 (16) | 0.0332 (16) | −0.0022 (13) | −0.0004 (12) | 0.0003 (13) |
C20 | 0.0322 (15) | 0.0419 (17) | 0.0360 (16) | −0.0060 (13) | −0.0007 (12) | −0.0046 (13) |
C21 | 0.0263 (14) | 0.0293 (14) | 0.0452 (17) | −0.0011 (12) | −0.0017 (12) | −0.0004 (12) |
C22 | 0.0280 (14) | 0.0425 (16) | 0.0307 (16) | 0.0013 (13) | 0.0024 (12) | 0.0027 (12) |
C23 | 0.0328 (15) | 0.0473 (18) | 0.0391 (17) | 0.0055 (14) | 0.0012 (13) | −0.0076 (14) |
C24 | 0.0404 (17) | 0.0456 (18) | 0.0382 (17) | −0.0020 (15) | 0.0022 (13) | −0.0134 (14) |
C25 | 0.0267 (14) | 0.0379 (16) | 0.0518 (19) | −0.0036 (13) | −0.0022 (13) | 0.0041 (14) |
C26 | 0.0275 (14) | 0.0515 (18) | 0.0383 (17) | 0.0093 (14) | 0.0022 (12) | 0.0031 (14) |
C27 | 0.0424 (17) | 0.0476 (19) | 0.051 (2) | −0.0014 (15) | 0.0002 (15) | −0.0026 (15) |
C28 | 0.0389 (17) | 0.081 (3) | 0.047 (2) | 0.0071 (17) | 0.0121 (15) | 0.0084 (18) |
N1—C5 | 1.334 (4) | C13—H13 | 0.9300 |
N1—C1 | 1.336 (4) | C14—C15 | 1.317 (4) |
N2—C22 | 1.364 (3) | C14—H14 | 0.9300 |
N2—C25 | 1.461 (4) | C15—C16 | 1.463 (4) |
N2—C26 | 1.461 (3) | C15—H15 | 0.9300 |
O1—C17 | 1.212 (3) | C16—C20 | 1.356 (4) |
O2—C18 | 1.381 (3) | C16—C17 | 1.453 (4) |
O2—C17 | 1.392 (3) | C18—C21 | 1.378 (4) |
C1—C2 | 1.372 (4) | C18—C19 | 1.398 (4) |
C1—H1 | 0.9300 | C19—C24 | 1.395 (4) |
C2—C3 | 1.396 (4) | C19—C20 | 1.409 (4) |
C2—H2 | 0.9300 | C20—H20 | 0.9300 |
C3—C4 | 1.392 (4) | C21—C22 | 1.413 (4) |
C3—C6 | 1.464 (4) | C21—H21 | 0.9300 |
C4—C5 | 1.379 (4) | C22—C23 | 1.417 (4) |
C4—H4 | 0.9300 | C23—C24 | 1.366 (4) |
C5—H5 | 0.9300 | C23—H23 | 0.9300 |
C6—C7 | 1.333 (4) | C24—H24 | 0.9300 |
C6—H6 | 0.9300 | C25—C27 | 1.506 (4) |
C7—C8 | 1.465 (4) | C25—H25A | 0.9700 |
C7—H7 | 0.9300 | C25—H25B | 0.9700 |
C8—C13 | 1.390 (4) | C26—C28 | 1.514 (4) |
C8—C9 | 1.403 (4) | C26—H26A | 0.9700 |
C9—C10 | 1.373 (4) | C26—H26B | 0.9700 |
C9—H9 | 0.9300 | C27—H27A | 0.9600 |
C10—C11 | 1.387 (4) | C27—H27B | 0.9600 |
C10—H10 | 0.9300 | C27—H27C | 0.9600 |
C11—C12 | 1.404 (4) | C28—H28A | 0.9600 |
C11—C14 | 1.475 (4) | C28—H28B | 0.9600 |
C12—C13 | 1.392 (4) | C28—H28C | 0.9600 |
C12—H12 | 0.9300 | ||
C5—N1—C1 | 115.4 (3) | C20—C16—C15 | 120.3 (3) |
C22—N2—C25 | 122.0 (2) | C17—C16—C15 | 121.0 (3) |
C22—N2—C26 | 122.1 (2) | O1—C17—O2 | 114.4 (3) |
C25—N2—C26 | 115.9 (2) | O1—C17—C16 | 127.7 (3) |
C18—O2—C17 | 122.1 (2) | O2—C17—C16 | 117.9 (2) |
N1—C1—C2 | 124.7 (3) | C21—C18—O2 | 116.6 (2) |
N1—C1—H1 | 117.6 | C21—C18—C19 | 123.5 (3) |
C2—C1—H1 | 117.6 | O2—C18—C19 | 119.9 (2) |
C1—C2—C3 | 119.5 (3) | C24—C19—C18 | 116.3 (2) |
C1—C2—H2 | 120.3 | C24—C19—C20 | 125.2 (3) |
C3—C2—H2 | 120.3 | C18—C19—C20 | 118.5 (3) |
C4—C3—C2 | 116.3 (3) | C16—C20—C19 | 122.7 (3) |
C4—C3—C6 | 120.6 (3) | C16—C20—H20 | 118.7 |
C2—C3—C6 | 123.1 (3) | C19—C20—H20 | 118.7 |
C5—C4—C3 | 119.6 (3) | C18—C21—C22 | 119.2 (3) |
C5—C4—H4 | 120.2 | C18—C21—H21 | 120.4 |
C3—C4—H4 | 120.2 | C22—C21—H21 | 120.4 |
N1—C5—C4 | 124.4 (3) | N2—C22—C21 | 121.4 (3) |
N1—C5—H5 | 117.8 | N2—C22—C23 | 120.9 (2) |
C4—C5—H5 | 117.8 | C21—C22—C23 | 117.7 (2) |
C7—C6—C3 | 126.4 (3) | C24—C23—C22 | 121.1 (3) |
C7—C6—H6 | 116.8 | C24—C23—H23 | 119.5 |
C3—C6—H6 | 116.8 | C22—C23—H23 | 119.5 |
C6—C7—C8 | 126.2 (3) | C23—C24—C19 | 122.2 (3) |
C6—C7—H7 | 116.9 | C23—C24—H24 | 118.9 |
C8—C7—H7 | 116.9 | C19—C24—H24 | 118.9 |
C13—C8—C9 | 117.0 (3) | N2—C25—C27 | 113.2 (2) |
C13—C8—C7 | 120.7 (3) | N2—C25—H25A | 108.9 |
C9—C8—C7 | 122.3 (3) | C27—C25—H25A | 108.9 |
C10—C9—C8 | 121.3 (3) | N2—C25—H25B | 108.9 |
C10—C9—H9 | 119.4 | C27—C25—H25B | 108.9 |
C8—C9—H9 | 119.4 | H25A—C25—H25B | 107.7 |
C9—C10—C11 | 122.0 (3) | N2—C26—C28 | 112.9 (2) |
C9—C10—H10 | 119.0 | N2—C26—H26A | 109.0 |
C11—C10—H10 | 119.0 | C28—C26—H26A | 109.0 |
C10—C11—C12 | 117.4 (3) | N2—C26—H26B | 109.0 |
C10—C11—C14 | 118.2 (3) | C28—C26—H26B | 109.0 |
C12—C11—C14 | 124.3 (3) | H26A—C26—H26B | 107.8 |
C13—C12—C11 | 120.4 (3) | C25—C27—H27A | 109.5 |
C13—C12—H12 | 119.8 | C25—C27—H27B | 109.5 |
C11—C12—H12 | 119.8 | H27A—C27—H27B | 109.5 |
C8—C13—C12 | 121.9 (3) | C25—C27—H27C | 109.5 |
C8—C13—H13 | 119.1 | H27A—C27—H27C | 109.5 |
C12—C13—H13 | 119.1 | H27B—C27—H27C | 109.5 |
C15—C14—C11 | 126.5 (3) | C26—C28—H28A | 109.5 |
C15—C14—H14 | 116.7 | C26—C28—H28B | 109.5 |
C11—C14—H14 | 116.7 | H28A—C28—H28B | 109.5 |
C14—C15—C16 | 128.8 (3) | C26—C28—H28C | 109.5 |
C14—C15—H15 | 115.6 | H28A—C28—H28C | 109.5 |
C16—C15—H15 | 115.6 | H28B—C28—H28C | 109.5 |
C20—C16—C17 | 118.7 (2) |
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−3/2, −y+1/2, z−1/2; (iii) −x+5/2, y−1/2, −z+3/2. |
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−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
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gong, 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
Helal, A., Rashid, M. H. O., Choi, C. & Kim, H. (2011). Tetrahedron, 67, 2794–2802. Web of Science CrossRef CAS Google Scholar
Jin, X., Uttamapinant, C. & Ting, A. Y. (2011). ChemBioChem, 12, 65–70. Web of Science CrossRef CAS PubMed Google Scholar
Jones, G., Jackson, W. R., Choi, C. & Bergmark, W. R. (1985). J. Phys. Chem. 89, 294–300. CrossRef CAS Web of Science Google Scholar
Nemkovich, N. A., Reis, H. & Baumann, W. (1997). J. Lumin. 71, 255–263. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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