anti-9,10-Di(1-naphth-yl)anthracene pyridine disolvate.

In the title compound, C(34)H(22)·2C(5)H(5)N, there is a crystallographic inversion center in the middle of the anthracene ring system. The dihedral angle between the mean planes of the anthracene and naphthalene ring systems is 83.96 (4)°. The crystal structure is stabilized by weak inter-molecular C-H⋯N and C-H⋯π inter-actions.

Related literature

For general background to blue-light-emitting materials, see: Zhang et al. (2003 ▶); Raghunath et al. (2006 ▶). For synthetic procedures, see: Kwon et al. (2002 ▶); Lee et al. (2008 ▶).

Experimental

Crystal data

C34H22·2C5H5N

M = 588.72

Monoclinic,

a = 8.9810 (18) Å

b = 24.166 (5) Å

c = 7.2740 (15) Å

β = 93.34 (3)°

V = 1576.0 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 174 K

0.16 × 0.16 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

16543 measured reflections

3897 independent reflections

3121 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.116

S = 1.03

3897 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809042706/lh2928sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042706/lh2928Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C34H22·2C5H5N	F(000) = 620
Mr = 588.72	Dx = 1.241 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5150 reflections
a = 8.9810 (18) Å	θ = 2.3–28.1°
b = 24.166 (5) Å	µ = 0.07 mm−1
c = 7.2740 (15) Å	T = 174 K
β = 93.34 (3)°	Block, colourless
V = 1576.0 (6) Å3	0.16 × 0.16 × 0.15 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	Rint = 0.026
φ and ω scans	θmax = 28.3°, θmin = 1.7°
16543 measured reflections	h = −11→11
3897 independent reflections	k = −31→32
3121 reflections with I > 2σ(I)	l = −9→9

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.4153P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.27 e Å−3
3897 reflections	Δρmin = −0.22 e Å−3
208 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.05625 (11)	0.54185 (4)	0.38731 (15)	0.0273 (2)
C2	0.11828 (13)	0.58393 (5)	0.27710 (17)	0.0338 (3)
H2	0.0574	0.6018	0.188	0.041*
C3	0.26455 (14)	0.59831 (5)	0.29986 (19)	0.0396 (3)
H3	0.3027	0.6256	0.2256	0.048*
C4	0.35912 (13)	0.57214 (5)	0.43571 (19)	0.0389 (3)
H4	0.4591	0.5822	0.4496	0.047*
C5	0.30516 (12)	0.53240 (5)	0.54615 (17)	0.0324 (3)
H5	0.3687	0.5158	0.6353	0.039*
C6	0.15163 (11)	0.51567 (4)	0.52738 (15)	0.0268 (2)
C7	−0.09396 (11)	0.52557 (4)	0.36048 (15)	0.0268 (2)
C8	−0.19254 (12)	0.55196 (5)	0.21282 (15)	0.0294 (2)
C9	−0.26471 (11)	0.60328 (5)	0.24560 (15)	0.0278 (2)
C10	−0.24646 (12)	0.63180 (5)	0.41558 (17)	0.0326 (3)
H10	−0.1844	0.6171	0.51	0.039*
C11	−0.31893 (14)	0.68071 (5)	0.4428 (2)	0.0424 (3)
H11	−0.3059	0.6989	0.5553	0.051*
C12	−0.41311 (14)	0.70367 (5)	0.3013 (2)	0.0459 (3)
H12	−0.4615	0.737	0.3205	0.055*
C13	−0.43357 (13)	0.67737 (5)	0.1369 (2)	0.0419 (3)
H13	−0.4966	0.6929	0.0449	0.05*
C14	−0.36078 (12)	0.62677 (5)	0.10307 (17)	0.0333 (3)
C15	−0.38159 (15)	0.59853 (6)	−0.06721 (18)	0.0446 (3)
H15	−0.4441	0.6136	−0.1607	0.054*
C16	−0.31118 (16)	0.54967 (7)	−0.09547 (18)	0.0491 (4)
H16	−0.3257	0.5316	−0.2079	0.059*
C17	−0.21627 (14)	0.52640 (6)	0.04517 (18)	0.0409 (3)
H17	−0.1687	0.493	0.0239	0.049*
N18	0.26262 (13)	0.69991 (6)	0.82489 (18)	0.0519 (3)
C19	0.19358 (17)	0.74566 (6)	0.8706 (2)	0.0503 (3)
H19	0.25	0.7778	0.8841	0.06*
C20	0.04512 (18)	0.74902 (8)	0.8994 (2)	0.0598 (4)
H20	0.0026	0.7826	0.9302	0.072*
C21	−0.03967 (18)	0.70250 (9)	0.8825 (2)	0.0664 (5)
H21	−0.1409	0.7036	0.9029	0.08*
C22	0.0270 (2)	0.65402 (8)	0.8348 (2)	0.0649 (5)
H22	−0.0279	0.6215	0.8212	0.078*
C23	0.1781 (2)	0.65463 (7)	0.8073 (2)	0.0588 (4)
H23	0.2232	0.6217	0.7748	0.071*

	U11	U22	U33	U12	U13	U23
C1	0.0250 (5)	0.0259 (5)	0.0313 (5)	0.0001 (4)	0.0047 (4)	−0.0023 (4)
C2	0.0320 (6)	0.0325 (6)	0.0373 (6)	−0.0009 (4)	0.0052 (5)	0.0035 (5)
C3	0.0358 (6)	0.0362 (6)	0.0479 (7)	−0.0078 (5)	0.0111 (5)	0.0043 (5)
C4	0.0252 (5)	0.0408 (7)	0.0512 (7)	−0.0072 (5)	0.0066 (5)	−0.0028 (6)
C5	0.0238 (5)	0.0333 (6)	0.0402 (6)	−0.0009 (4)	0.0015 (4)	−0.0037 (5)
C6	0.0238 (5)	0.0255 (5)	0.0315 (5)	0.0007 (4)	0.0038 (4)	−0.0040 (4)
C7	0.0252 (5)	0.0254 (5)	0.0298 (5)	0.0015 (4)	0.0019 (4)	−0.0029 (4)
C8	0.0255 (5)	0.0329 (6)	0.0298 (5)	−0.0010 (4)	0.0019 (4)	0.0001 (4)
C9	0.0215 (5)	0.0301 (5)	0.0319 (5)	−0.0034 (4)	0.0015 (4)	0.0034 (4)
C10	0.0269 (5)	0.0322 (6)	0.0383 (6)	−0.0001 (4)	−0.0007 (4)	−0.0020 (5)
C11	0.0362 (6)	0.0365 (7)	0.0546 (8)	0.0003 (5)	0.0033 (6)	−0.0098 (6)
C12	0.0325 (6)	0.0305 (6)	0.0748 (10)	0.0043 (5)	0.0053 (6)	0.0014 (6)
C13	0.0273 (6)	0.0391 (7)	0.0590 (8)	0.0016 (5)	−0.0010 (5)	0.0169 (6)
C14	0.0242 (5)	0.0377 (6)	0.0379 (6)	−0.0032 (4)	−0.0001 (4)	0.0094 (5)
C15	0.0379 (7)	0.0612 (9)	0.0338 (6)	−0.0026 (6)	−0.0071 (5)	0.0092 (6)
C16	0.0494 (8)	0.0666 (10)	0.0303 (6)	−0.0016 (7)	−0.0047 (6)	−0.0088 (6)
C17	0.0407 (7)	0.0451 (7)	0.0366 (7)	0.0031 (5)	0.0006 (5)	−0.0087 (5)
N18	0.0425 (6)	0.0580 (8)	0.0549 (7)	0.0085 (5)	−0.0004 (5)	0.0005 (6)
C19	0.0489 (8)	0.0498 (8)	0.0515 (8)	−0.0012 (6)	−0.0031 (6)	−0.0031 (7)
C20	0.0540 (9)	0.0713 (11)	0.0545 (9)	0.0175 (8)	0.0065 (7)	−0.0048 (8)
C21	0.0395 (8)	0.1033 (15)	0.0563 (10)	−0.0012 (9)	0.0011 (7)	0.0171 (10)
C22	0.0730 (11)	0.0685 (11)	0.0503 (9)	−0.0279 (9)	−0.0201 (8)	0.0170 (8)
C23	0.0767 (11)	0.0469 (9)	0.0515 (9)	0.0112 (8)	−0.0073 (8)	−0.0021 (7)

C1—C7	1.4079 (15)	C12—C13	1.357 (2)
C1—C2	1.4281 (16)	C12—H12	0.93
C1—C6	1.4388 (16)	C13—C14	1.4149 (18)
C2—C3	1.3596 (17)	C13—H13	0.93
C2—H2	0.93	C14—C15	1.4170 (19)
C3—C4	1.4143 (19)	C15—C16	1.361 (2)
C3—H3	0.93	C15—H15	0.93
C4—C5	1.3593 (17)	C16—C17	1.4099 (19)
C4—H4	0.93	C16—H16	0.93
C5—C6	1.4358 (15)	C17—H17	0.93
C5—H5	0.93	N18—C19	1.3197 (19)
C6—C7i	1.4057 (15)	N18—C23	1.333 (2)
C7—C6i	1.4057 (15)	C19—C20	1.364 (2)
C7—C8	1.4944 (16)	C19—H19	0.93
C8—C17	1.3725 (17)	C20—C21	1.359 (3)
C8—C9	1.4260 (15)	C20—H20	0.93
C9—C10	1.4166 (16)	C21—C22	1.370 (3)
C9—C14	1.4273 (16)	C21—H21	0.93
C10—C11	1.3693 (17)	C22—C23	1.383 (3)
C10—H10	0.93	C22—H22	0.93
C11—C12	1.408 (2)	C23—H23	0.93
C11—H11	0.93
C7—C1—C2	121.55 (10)	C13—C12—H12	119.9
C7—C1—C6	120.10 (10)	C11—C12—H12	119.9
C2—C1—C6	118.35 (10)	C12—C13—C14	121.19 (12)
C3—C2—C1	121.30 (11)	C12—C13—H13	119.4
C3—C2—H2	119.4	C14—C13—H13	119.4
C1—C2—H2	119.4	C13—C14—C15	121.98 (12)
C2—C3—C4	120.49 (11)	C13—C14—C9	118.89 (12)
C2—C3—H3	119.8	C15—C14—C9	119.13 (12)
C4—C3—H3	119.8	C16—C15—C14	120.74 (12)
C5—C4—C3	120.57 (11)	C16—C15—H15	119.6
C5—C4—H4	119.7	C14—C15—H15	119.6
C3—C4—H4	119.7	C15—C16—C17	120.21 (12)
C4—C5—C6	121.07 (11)	C15—C16—H16	119.9
C4—C5—H5	119.5	C17—C16—H16	119.9
C6—C5—H5	119.5	C8—C17—C16	121.42 (13)
C7i—C6—C5	121.91 (10)	C8—C17—H17	119.3
C7i—C6—C1	119.89 (9)	C16—C17—H17	119.3
C5—C6—C1	118.19 (10)	C19—N18—C23	116.01 (14)
C6i—C7—C1	120.01 (10)	N18—C19—C20	124.50 (15)
C6i—C7—C8	119.79 (9)	N18—C19—H19	117.8
C1—C7—C8	120.20 (10)	C20—C19—H19	117.8
C17—C8—C9	119.43 (11)	C21—C20—C19	118.96 (16)
C17—C8—C7	120.09 (11)	C21—C20—H20	120.5
C9—C8—C7	120.47 (10)	C19—C20—H20	120.5
C10—C9—C8	122.58 (10)	C20—C21—C22	118.66 (15)
C10—C9—C14	118.34 (11)	C20—C21—H21	120.7
C8—C9—C14	119.07 (10)	C22—C21—H21	120.7
C11—C10—C9	120.96 (11)	C21—C22—C23	118.33 (16)
C11—C10—H10	119.5	C21—C22—H22	120.8
C9—C10—H10	119.5	C23—C22—H22	120.8
C10—C11—C12	120.33 (13)	N18—C23—C22	123.54 (16)
C10—C11—H11	119.8	N18—C23—H23	118.2
C12—C11—H11	119.8	C22—C23—H23	118.2
C13—C12—C11	120.29 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N18ii	0.93	2.62	3.4887 (19)	156
C4—H4···Cg1iii	0.93	2.86	3.6026 (15)	138
C16—H16···Cg2iv	0.93	2.85	3.6177 (18)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N18i	0.93	2.62	3.4887 (19)	156
C4—H4⋯Cg1ii	0.93	2.86	3.6026 (15)	138
C16—H16⋯Cg2iii	0.93	2.85	3.6177 (18)	141

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C9–C14 and C1–C6 rings, respectively.