4-(Anthracen-9-yl)-2-phenyl-6-(pyridin-2-yl)pyridine

Wang, H.-W.; Ren, J.; Ye, W.-B.; Yang, J.-X.

doi:10.1107/S1600536812012299

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1210

doi:10.1107/S1600536812012299

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4-(Anthracen-9-yl)-2-phenyl-6-(pyridin-2-yl)pyridine

Hao-Wei Wang,^a Jun Ren,^a Wen-Bo Ye ^a and Jia-Xiang Yang ^a ^*

^aDeparment of Chemistry, Anhui University, Hefei 230039, People's Republic of China
^*Correspondence e-mail: jxyang@ahu.edu.cn

(Received 29 February 2012; accepted 21 March 2012; online 28 March 2012)

In the title compound, C₃₀H₂₀N₂, the anthracene ring system is approximately planar [maximum deviation = 0.035 (2) Å] and is nearly perpendicular to the central pyridine ring, making a dihedral angle of 75.73 (7)°. The terminal pyridine ring and the phenyl ring are oriented at dihedral angles of 8.11 (10) and 13.22 (10)°, respectively, to the central pyridine ring.

Related literature

For applications of aromatic conjugated organic compounds, see: Nishihara et al. (1989 ); Mi et al. (2003 ); Roberto et al. (2000 ).

Experimental

Crystal data

C₃₀H₂₀N₂
M_r = 408.48
Monoclinic, P 2₁ /c
a = 12.6420 (3) Å
b = 14.8499 (4) Å
c = 11.8707 (3) Å
β = 104.006 (2)°
V = 2162.26 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
35644 measured reflections
4951 independent reflections
3128 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.215
S = 1.33
4951 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812012299/xu5476sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012299/xu5476Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812012299/xu5476Isup3.cml

checkCIF report

Comment top

The aromatic conjugated organic compounds are investigated with great interest due to their potential applications in optical image processing, all-optical switching, organic light emitting diodes (OLEDs) and integrated optical devices (Nishihara et al., 1989; Mi et al., 2003; Roberto et al., 2000). As a part of our continuing studies of the synthesis and characterization of optical materials, we have prepared a new anthracene derivative containing two pyridine rings and investigated its crystal structure.

The molecule structure of (I) is shown in Fig. 1. Two pyridine rings makes the dihedral angle of 8.11 (10)°. The anthracen moiety is almost planar, and make the dihedral angles of 75.73 (7)° and 67.84 (2)° with two pyridine rings, respectively.

Related literature top

For applications of aromatic conjugated organic compounds, see: Nishihara et al. (1989); Mi et al. (2003); Roberto et al. (2000).

Experimental top

3-(Anthracen-9-yl)-1-phenylprop-2-en-1-one (1.54 g, 5.0 mmol), 2-acetylpyridine (1.82 g, 15 mmol) and NaOH (0.20 g, 5.0 mmol) were crashed together with a pestle and mortar for 3 h. The light yellow powder was added to a stirred solution of ammonium acetate (15.4 g, 200.0 mmol) in ethanol (200 ml). The reaction mixture was heated at reflux. Thin layer chromatography analysis tracking reaction, evaporated solvent, extracted with dichloromethane, and dried to afford the product. It was purified by flash column chromatography on silica. Elution with petroleum/ethyl acetate (10:1) gave a white solid (yield; 1.3 g, 65%). Single crystals of (I) were grown by slow evaporation of a dichloromethane/ethyl acetate (1:1) solution.

Structure description top

For applications of aromatic conjugated organic compounds, see: Nishihara et al. (1989); Mi et al. (2003); Roberto et al. (2000).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I).

4-(Anthracen-9-yl)-2-phenyl-6-(pyridin-2-yl)pyridine top

Crystal data top

C₃₀H₂₀N₂	F(000) = 856
M_r = 408.48	D_x = 1.255 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5640 reflections
a = 12.6420 (3) Å	θ = 2.2–22.7°
b = 14.8499 (4) Å	µ = 0.07 mm⁻¹
c = 11.8707 (3) Å	T = 298 K
β = 104.006 (2)°	Block, pale yellow
V = 2162.26 (9) Å³	0.2 × 0.2 × 0.2 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3128 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
φ and ω scans	h = −16→16
35644 measured reflections	k = −19→17
4951 independent reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.215	H-atom parameters constrained
S = 1.33	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
4951 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₃₀H₂₀N₂	V = 2162.26 (9) Å³
M_r = 408.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6420 (3) Å	µ = 0.07 mm⁻¹
b = 14.8499 (4) Å	T = 298 K
c = 11.8707 (3) Å	0.2 × 0.2 × 0.2 mm
β = 104.006 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3128 reflections with I > 2σ(I)
35644 measured reflections	R_int = 0.038
4951 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.215	H-atom parameters constrained
S = 1.33	Δρ_max = 0.20 e Å⁻³
4951 reflections	Δρ_min = −0.20 e Å⁻³
289 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.56725 (12)	0.37331 (10)	0.11808 (12)	0.0487 (4)
C18	0.64872 (14)	0.37932 (12)	0.21431 (15)	0.0488 (5)
C20	0.47454 (15)	0.29870 (13)	−0.05928 (15)	0.0509 (5)
C10	0.82717 (15)	0.18045 (13)	0.18202 (16)	0.0529 (5)
N2	0.71173 (15)	0.45087 (13)	0.40278 (15)	0.0651 (5)
C16	0.65564 (15)	0.24508 (14)	0.05996 (16)	0.0533 (5)
H16	0.6560	0.2001	0.0056	0.064*
C17	0.57066 (15)	0.30714 (13)	0.04214 (15)	0.0481 (5)
C6	0.82357 (16)	0.11106 (13)	0.26209 (17)	0.0551 (5)
C9	0.90771 (15)	0.18139 (13)	0.11945 (17)	0.0547 (5)
C15	0.73990 (14)	0.25080 (13)	0.15945 (17)	0.0522 (5)
C5	0.90315 (17)	0.04023 (14)	0.27789 (19)	0.0619 (6)
C30	0.47702 (17)	0.24029 (15)	−0.14691 (16)	0.0588 (5)
H30	0.5407	0.2087	−0.1464	0.071*
C25	0.63672 (15)	0.44908 (12)	0.29968 (16)	0.0479 (4)
C8	0.98524 (16)	0.10877 (15)	0.13417 (18)	0.0612 (6)
C19	0.73694 (15)	0.31995 (13)	0.23649 (17)	0.0547 (5)
H19	0.7933	0.3269	0.3027	0.066*
C1	0.74384 (18)	0.10684 (15)	0.32911 (19)	0.0646 (6)
H1	0.6908	0.1515	0.3199	0.078*
C29	0.69808 (19)	0.51083 (16)	0.48382 (18)	0.0668 (6)
H29	0.7490	0.5117	0.5550	0.080*
C7	0.98102 (17)	0.04122 (15)	0.2135 (2)	0.0675 (6)
H7	1.0322	−0.0050	0.2239	0.081*
C13	0.99391 (19)	0.24831 (18)	−0.0222 (2)	0.0722 (6)
H13	0.9983	0.2948	−0.0733	0.087*
C14	0.91720 (17)	0.25100 (16)	0.03936 (18)	0.0634 (6)
H14	0.8692	0.2994	0.0294	0.076*
C26	0.54987 (18)	0.50785 (16)	0.2783 (2)	0.0708 (6)
H26	0.4988	0.5066	0.2072	0.085*
C24	0.38033 (18)	0.34689 (19)	−0.06388 (19)	0.0791 (7)
H24	0.3781	0.3885	−0.0060	0.095*
C4	0.8981 (2)	−0.02999 (16)	0.3592 (2)	0.0798 (7)
H4	0.9490	−0.0764	0.3699	0.096*
C28	0.6140 (2)	0.56951 (17)	0.4665 (2)	0.0732 (7)
H28	0.6075	0.6099	0.5243	0.088*
C2	0.7437 (2)	0.03950 (17)	0.4056 (2)	0.0762 (7)
H2	0.6917	0.0391	0.4491	0.091*
C12	1.0679 (2)	0.1750 (2)	−0.0096 (2)	0.0813 (7)
H12	1.1196	0.1728	−0.0536	0.098*
C11	1.06313 (19)	0.10878 (18)	0.0663 (2)	0.0780 (7)
H11	1.1126	0.0615	0.0744	0.094*
C3	0.8214 (2)	−0.03005 (19)	0.4202 (2)	0.0858 (8)
H3	0.8197	−0.0764	0.4724	0.103*
C27	0.5389 (2)	0.56830 (18)	0.3625 (2)	0.0873 (8)
H27	0.4805	0.6082	0.3485	0.105*
C22	0.2928 (2)	0.2736 (2)	−0.2388 (2)	0.0911 (9)
H22	0.2314	0.2637	−0.2989	0.109*
C21	0.3868 (2)	0.22766 (18)	−0.23564 (19)	0.0789 (7)
H21	0.3896	0.1872	−0.2947	0.095*
C23	0.2893 (2)	0.3338 (2)	−0.1538 (2)	0.1001 (10)
H23	0.2258	0.3662	−0.1561	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0500 (9)	0.0484 (10)	0.0466 (8)	0.0047 (7)	0.0096 (7)	0.0033 (7)
C18	0.0479 (10)	0.0460 (11)	0.0515 (10)	0.0006 (8)	0.0099 (8)	0.0042 (8)
C20	0.0507 (11)	0.0549 (12)	0.0459 (9)	0.0089 (8)	0.0092 (8)	0.0081 (9)
C10	0.0471 (10)	0.0473 (11)	0.0576 (10)	0.0069 (8)	−0.0006 (8)	−0.0051 (9)
N2	0.0652 (11)	0.0657 (12)	0.0604 (10)	0.0019 (9)	0.0072 (8)	−0.0023 (9)
C16	0.0526 (11)	0.0504 (12)	0.0537 (10)	0.0086 (8)	0.0069 (8)	−0.0021 (9)
C17	0.0492 (10)	0.0491 (11)	0.0455 (9)	0.0037 (8)	0.0105 (8)	0.0064 (8)
C6	0.0487 (10)	0.0481 (12)	0.0603 (11)	0.0038 (8)	−0.0028 (8)	−0.0032 (9)
C9	0.0477 (10)	0.0511 (12)	0.0578 (11)	0.0050 (8)	−0.0021 (8)	−0.0067 (9)
C15	0.0483 (10)	0.0449 (11)	0.0603 (11)	0.0059 (8)	0.0069 (8)	0.0028 (9)
C5	0.0532 (12)	0.0502 (12)	0.0728 (13)	0.0069 (9)	−0.0032 (10)	−0.0010 (10)
C30	0.0584 (12)	0.0651 (13)	0.0499 (10)	0.0119 (10)	0.0073 (9)	−0.0045 (10)
C25	0.0503 (10)	0.0412 (10)	0.0519 (10)	−0.0012 (8)	0.0116 (8)	0.0042 (8)
C8	0.0476 (11)	0.0617 (14)	0.0687 (13)	0.0084 (9)	0.0031 (9)	−0.0096 (11)
C19	0.0495 (10)	0.0497 (12)	0.0583 (11)	0.0041 (8)	0.0001 (8)	0.0009 (9)
C1	0.0580 (12)	0.0584 (14)	0.0726 (13)	0.0030 (10)	0.0064 (10)	0.0001 (11)
C29	0.0793 (15)	0.0669 (15)	0.0522 (11)	−0.0039 (11)	0.0117 (10)	−0.0084 (10)
C7	0.0564 (12)	0.0540 (13)	0.0845 (15)	0.0153 (10)	0.0024 (11)	0.0009 (11)
C13	0.0628 (13)	0.0835 (17)	0.0662 (13)	−0.0037 (12)	0.0080 (11)	0.0032 (12)
C14	0.0548 (12)	0.0640 (14)	0.0648 (12)	0.0050 (10)	0.0017 (10)	−0.0022 (11)
C26	0.0701 (14)	0.0677 (15)	0.0673 (13)	0.0178 (11)	0.0026 (10)	−0.0121 (11)
C24	0.0676 (15)	0.1003 (19)	0.0601 (12)	0.0295 (13)	−0.0026 (10)	−0.0151 (13)
C4	0.0747 (16)	0.0581 (15)	0.0971 (17)	0.0133 (12)	0.0022 (14)	0.0174 (13)
C28	0.0850 (16)	0.0680 (15)	0.0690 (14)	0.0044 (12)	0.0233 (12)	−0.0180 (12)
C2	0.0725 (15)	0.0716 (16)	0.0825 (15)	−0.0037 (12)	0.0151 (12)	0.0121 (13)
C12	0.0626 (14)	0.099 (2)	0.0828 (16)	0.0047 (14)	0.0188 (12)	−0.0051 (15)
C11	0.0585 (13)	0.0804 (17)	0.0913 (17)	0.0164 (12)	0.0109 (12)	−0.0061 (15)
C3	0.0856 (18)	0.0694 (17)	0.0977 (18)	−0.0010 (13)	0.0133 (15)	0.0244 (14)
C27	0.0881 (18)	0.0794 (18)	0.0926 (18)	0.0285 (14)	0.0182 (14)	−0.0137 (15)
C22	0.0741 (17)	0.128 (2)	0.0582 (13)	0.0138 (16)	−0.0095 (12)	−0.0087 (15)
C21	0.0836 (17)	0.0906 (18)	0.0563 (12)	0.0096 (14)	0.0047 (11)	−0.0143 (12)
C23	0.0695 (16)	0.150 (3)	0.0691 (15)	0.0432 (17)	−0.0065 (12)	−0.0183 (17)

Geometric parameters (Å, º) top

N1—C17	1.341 (2)	C1—H1	0.9300
N1—C18	1.343 (2)	C29—C28	1.351 (3)
C18—C19	1.396 (3)	C29—H29	0.9300
C18—C25	1.482 (3)	C7—H7	0.9300
C20—C30	1.361 (3)	C13—C14	1.349 (3)
C20—C24	1.379 (3)	C13—C12	1.420 (4)
C20—C17	1.494 (2)	C13—H13	0.9300
C10—C9	1.398 (3)	C14—H14	0.9300
C10—C6	1.410 (3)	C26—C27	1.375 (3)
C10—C15	1.496 (3)	C26—H26	0.9300
N2—C29	1.352 (3)	C24—C23	1.381 (3)
N2—C25	1.355 (2)	C24—H24	0.9300
C16—C15	1.388 (2)	C4—C3	1.344 (4)
C16—C17	1.392 (3)	C4—H4	0.9300
C16—H16	0.9300	C28—C27	1.363 (3)
C6—C1	1.429 (3)	C28—H28	0.9300
C6—C5	1.436 (3)	C2—C3	1.407 (4)
C9—C14	1.429 (3)	C2—H2	0.9300
C9—C8	1.439 (3)	C12—C11	1.345 (4)
C15—C19	1.382 (3)	C12—H12	0.9300
C5—C7	1.385 (3)	C11—H11	0.9300
C5—C4	1.433 (3)	C3—H3	0.9300
C30—C21	1.365 (3)	C27—H27	0.9300
C30—H30	0.9300	C22—C23	1.357 (4)
C25—C26	1.377 (3)	C22—C21	1.363 (4)
C8—C7	1.386 (3)	C22—H22	0.9300
C8—C11	1.415 (3)	C21—H21	0.9300
C19—H19	0.9300	C23—H23	0.9300
C1—C2	1.351 (3)

C17—N1—C18	118.52 (15)	N2—C29—H29	118.4
N1—C18—C19	122.12 (17)	C5—C7—C8	122.16 (19)
N1—C18—C25	116.33 (16)	C5—C7—H7	118.9
C19—C18—C25	121.45 (16)	C8—C7—H7	118.9
C30—C20—C24	118.68 (18)	C14—C13—C12	120.5 (2)
C30—C20—C17	120.31 (17)	C14—C13—H13	119.8
C24—C20—C17	120.95 (18)	C12—C13—H13	119.8
C9—C10—C6	120.79 (17)	C13—C14—C9	121.8 (2)
C9—C10—C15	119.89 (18)	C13—C14—H14	119.1
C6—C10—C15	119.23 (19)	C9—C14—H14	119.1
C29—N2—C25	118.27 (18)	C27—C26—C25	119.7 (2)
C15—C16—C17	119.58 (18)	C27—C26—H26	120.1
C15—C16—H16	120.2	C25—C26—H26	120.1
C17—C16—H16	120.2	C20—C24—C23	120.5 (2)
N1—C17—C16	122.14 (16)	C20—C24—H24	119.7
N1—C17—C20	116.79 (16)	C23—C24—H24	119.7
C16—C17—C20	120.93 (17)	C3—C4—C5	121.3 (2)
C10—C6—C1	123.35 (18)	C3—C4—H4	119.4
C10—C6—C5	119.2 (2)	C5—C4—H4	119.4
C1—C6—C5	117.49 (19)	C29—C28—C27	118.6 (2)
C10—C9—C14	123.36 (18)	C29—C28—H28	120.7
C10—C9—C8	119.35 (19)	C27—C28—H28	120.7
C14—C9—C8	117.3 (2)	C1—C2—C3	120.8 (3)
C19—C15—C16	118.06 (16)	C1—C2—H2	119.6
C19—C15—C10	122.51 (16)	C3—C2—H2	119.6
C16—C15—C10	119.37 (17)	C11—C12—C13	119.7 (2)
C7—C5—C4	122.2 (2)	C11—C12—H12	120.1
C7—C5—C6	119.3 (2)	C13—C12—H12	120.1
C4—C5—C6	118.5 (2)	C12—C11—C8	122.1 (2)
C20—C30—C21	120.5 (2)	C12—C11—H11	118.9
C20—C30—H30	119.7	C8—C11—H11	118.9
C21—C30—H30	119.7	C4—C3—C2	120.4 (2)
N2—C25—C26	120.42 (18)	C4—C3—H3	119.8
N2—C25—C18	117.79 (16)	C2—C3—H3	119.8
C26—C25—C18	121.73 (17)	C28—C27—C26	119.7 (2)
C7—C8—C11	122.3 (2)	C28—C27—H27	120.1
C7—C8—C9	119.2 (2)	C26—C27—H27	120.1
C11—C8—C9	118.6 (2)	C23—C22—C21	119.6 (2)
C15—C19—C18	119.54 (16)	C23—C22—H22	120.2
C15—C19—H19	120.2	C21—C22—H22	120.2
C18—C19—H19	120.2	C22—C21—C30	120.8 (2)
C2—C1—C6	121.5 (2)	C22—C21—H21	119.6
C2—C1—H1	119.3	C30—C21—H21	119.6
C6—C1—H1	119.3	C22—C23—C24	119.8 (2)
C28—C29—N2	123.2 (2)	C22—C23—H23	120.1
C28—C29—H29	118.4	C24—C23—H23	120.1

Experimental details

Crystal data
Chemical formula	C₃₀H₂₀N₂
M_r	408.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.6420 (3), 14.8499 (4), 11.8707 (3)
β (°)	104.006 (2)
V (Å³)	2162.26 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.2 × 0.2 × 0.2

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	35644, 4951, 3128
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.215, 1.33
No. of reflections	4951
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Acknowledgements

The work was supported by the National Natural Science Foundation of China (50873001, 21071001) and the Education Committee of Anhui Province, China (KJ2011Z338).

References

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