Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026918/cv2255sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026918/cv2255Isup2.hkl |
CCDC reference: 654949
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.002 Å
- R factor = 0.047
- wR factor = 0.151
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.621 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.04 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.62 e/A
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared according to the reported procedure of Rowland et al. (2001). Yellow single crystals suitable for X-ray diffraction were obtained by recrystallization from dimethyl sulfoxide.
C-bound H atoms were placed in calculated positions with C—H = 0.95–0.99 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C). Atom H1N was located in a difference Fourier map and refined isotropically with a bond restraint of N—H = 0.86 (2) Å.
Anthracene is a polycyclic aromatic hydrocarbon that has been widely used as a signaling subunit for both cation (Gunnlaugsson et al., 2003) and anion (Chen & Chen, 2004; Kim & Yoon, 2002) sensing due to its well known photophysical properties and high fluorescence. We here report the crystal structure of the title compound, (I).
In (I) (Fig. 1), the bond lengths and angles are within normal ranges. The anthracene ring system is slightly twisted with a dihedral angle of 1.22 (1)° between the two utmost rings. The anthracene mean plane and pyridin ring make a dihedral angle of 72.6 (1)°. The intramolecular hydrogen bond N1—H1N···N2 (Table 1) influences molecular conformation. The short contact between the anthracene fragments of the neighbouring molecules - C9···C14ii of 3.431 (2) Å and C1···C3iii of 3.591 (2) Å [symmetry codes: (ii) 1 - x, 2 - y,1 - z; (iii) 1 - x, 1 - y, 1 - z] - show an existence of π···π interactions, which form stacks of the molecules parallel to b axis. The crystal packing exhibits also weak intermolecular C—H···O hydrogen bonds.
For crystal structures of isomers of the title compound, see: Huang et al. (2004); Gu et al. (2006); Kubo et al. (2007). For the application of anthracene's derivatives, see: Gunnlaugsson et al. (2003); Chen & Chen (2004); Kim & Yoon (2002).
For related literature, see: Rowland et al. (2001).
Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atomic numbering. |
C21H16N2O | F(000) = 656 |
Mr = 312.36 | Dx = 1.363 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9693 reflections |
a = 10.0182 (3) Å | θ = 3.2–27.5° |
b = 8.1082 (3) Å | µ = 0.09 mm−1 |
c = 19.2442 (6) Å | T = 153 K |
β = 103.070 (1)° | Block, yellow |
V = 1522.70 (9) Å3 | 0.25 × 0.25 × 0.06 mm |
Z = 4 |
Rigaku RAXIS-RAPID diffractometer | 2304 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.5°, θmin = 3.3° |
ω scans | h = −12→13 |
14372 measured reflections | k = −10→10 |
3479 independent reflections | l = −24→24 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.098P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
3479 reflections | Δρmax = 0.62 e Å−3 |
222 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.013 (3) |
C21H16N2O | V = 1522.70 (9) Å3 |
Mr = 312.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.0182 (3) Å | µ = 0.09 mm−1 |
b = 8.1082 (3) Å | T = 153 K |
c = 19.2442 (6) Å | 0.25 × 0.25 × 0.06 mm |
β = 103.070 (1)° |
Rigaku RAXIS-RAPID diffractometer | 2304 reflections with I > 2σ(I) |
14372 measured reflections | Rint = 0.032 |
3479 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.62 e Å−3 |
3479 reflections | Δρmin = −0.20 e Å−3 |
222 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. |
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 | ||
O1 | 0.03419 (13) | 0.86927 (15) | 0.62684 (7) | 0.0469 (4) | |
N1 | 0.16317 (14) | 0.73494 (17) | 0.56145 (7) | 0.0346 (3) | |
N2 | 0.07086 (15) | 0.44338 (17) | 0.59240 (8) | 0.0389 (4) | |
C1 | 0.39511 (17) | 0.70846 (19) | 0.45469 (8) | 0.0355 (4) | |
H1 | 0.2979 | 0.7049 | 0.4410 | 0.043* | |
C2 | 0.46983 (18) | 0.6366 (2) | 0.41213 (9) | 0.0392 (4) | |
H2 | 0.4244 | 0.5839 | 0.3692 | 0.047* | |
C3 | 0.61427 (18) | 0.6397 (2) | 0.43115 (9) | 0.0391 (4) | |
H3 | 0.6652 | 0.5910 | 0.4004 | 0.047* | |
C4 | 0.68103 (18) | 0.71105 (19) | 0.49267 (9) | 0.0378 (4) | |
H4 | 0.7784 | 0.7108 | 0.5050 | 0.045* | |
C5 | 0.67089 (19) | 1.0119 (2) | 0.71376 (9) | 0.0426 (4) | |
H5 | 0.7681 | 1.0085 | 0.7272 | 0.051* | |
C6 | 0.6004 (2) | 1.0877 (2) | 0.75709 (10) | 0.0480 (5) | |
H6 | 0.6483 | 1.1382 | 0.8001 | 0.058* | |
C7 | 0.4556 (2) | 1.0915 (2) | 0.73833 (9) | 0.0458 (5) | |
H7 | 0.4068 | 1.1448 | 0.7690 | 0.055* | |
C8 | 0.38483 (19) | 1.0198 (2) | 0.67683 (9) | 0.0396 (4) | |
H8 | 0.2875 | 1.0222 | 0.6659 | 0.048* | |
C9 | 0.38519 (16) | 0.86933 (18) | 0.56359 (8) | 0.0316 (4) | |
C10 | 0.67400 (17) | 0.86240 (19) | 0.60291 (9) | 0.0351 (4) | |
H10 | 0.7713 | 0.8628 | 0.6156 | 0.042* | |
C11 | 0.60121 (17) | 0.93700 (19) | 0.64807 (8) | 0.0345 (4) | |
C12 | 0.45425 (17) | 0.94096 (18) | 0.62850 (8) | 0.0326 (4) | |
C13 | 0.45931 (15) | 0.78882 (17) | 0.51927 (8) | 0.0298 (3) | |
C14 | 0.60675 (16) | 0.78706 (18) | 0.53946 (8) | 0.0324 (4) | |
C15 | 0.23042 (16) | 0.87963 (19) | 0.53993 (9) | 0.0343 (4) | |
H15A | 0.1982 | 0.9795 | 0.5608 | 0.041* | |
H15B | 0.2042 | 0.8904 | 0.4874 | 0.041* | |
C16 | 0.07404 (16) | 0.74078 (19) | 0.60383 (9) | 0.0340 (4) | |
C17 | 0.02651 (16) | 0.5742 (2) | 0.62342 (8) | 0.0336 (4) | |
C18 | −0.05583 (17) | 0.5611 (2) | 0.67204 (9) | 0.0398 (4) | |
H18 | −0.0867 | 0.6568 | 0.6922 | 0.048* | |
C19 | −0.09223 (19) | 0.4049 (2) | 0.69066 (10) | 0.0459 (4) | |
H19 | −0.1476 | 0.3916 | 0.7243 | 0.055* | |
C20 | −0.04654 (19) | 0.2690 (2) | 0.65940 (10) | 0.0463 (4) | |
H20 | −0.0698 | 0.1605 | 0.6711 | 0.056* | |
C21 | 0.03386 (18) | 0.2950 (2) | 0.61073 (10) | 0.0438 (4) | |
H21 | 0.0645 | 0.2012 | 0.5891 | 0.053* | |
H1N | 0.1791 (18) | 0.637 (2) | 0.5475 (10) | 0.040 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0505 (7) | 0.0364 (7) | 0.0597 (8) | 0.0007 (5) | 0.0252 (7) | −0.0038 (6) |
N1 | 0.0384 (7) | 0.0304 (7) | 0.0360 (7) | −0.0010 (6) | 0.0104 (6) | −0.0006 (6) |
N2 | 0.0381 (7) | 0.0342 (7) | 0.0443 (8) | 0.0013 (6) | 0.0096 (6) | 0.0027 (6) |
C1 | 0.0410 (9) | 0.0327 (8) | 0.0318 (8) | −0.0006 (7) | 0.0060 (7) | 0.0019 (6) |
C2 | 0.0525 (10) | 0.0330 (9) | 0.0329 (9) | −0.0006 (7) | 0.0112 (8) | −0.0018 (7) |
C3 | 0.0517 (10) | 0.0321 (8) | 0.0378 (9) | 0.0073 (7) | 0.0188 (8) | 0.0035 (7) |
C4 | 0.0419 (9) | 0.0314 (8) | 0.0422 (9) | 0.0037 (7) | 0.0140 (8) | 0.0075 (7) |
C5 | 0.0509 (10) | 0.0377 (9) | 0.0358 (9) | −0.0104 (8) | 0.0028 (8) | 0.0047 (7) |
C6 | 0.0688 (13) | 0.0386 (10) | 0.0321 (9) | −0.0098 (9) | 0.0024 (9) | −0.0012 (7) |
C7 | 0.0735 (13) | 0.0332 (9) | 0.0328 (9) | 0.0015 (9) | 0.0162 (9) | −0.0004 (7) |
C8 | 0.0547 (10) | 0.0318 (8) | 0.0339 (9) | 0.0015 (7) | 0.0130 (8) | 0.0038 (7) |
C9 | 0.0376 (8) | 0.0269 (7) | 0.0307 (8) | −0.0021 (6) | 0.0088 (7) | 0.0054 (6) |
C10 | 0.0360 (8) | 0.0320 (8) | 0.0358 (9) | −0.0036 (6) | 0.0052 (7) | 0.0081 (7) |
C11 | 0.0441 (9) | 0.0281 (8) | 0.0298 (8) | −0.0064 (6) | 0.0051 (7) | 0.0056 (6) |
C12 | 0.0454 (9) | 0.0248 (7) | 0.0287 (8) | −0.0013 (6) | 0.0106 (7) | 0.0048 (6) |
C13 | 0.0351 (8) | 0.0252 (7) | 0.0294 (8) | −0.0007 (6) | 0.0080 (7) | 0.0036 (6) |
C14 | 0.0380 (9) | 0.0260 (7) | 0.0342 (8) | −0.0005 (6) | 0.0103 (7) | 0.0073 (6) |
C15 | 0.0398 (8) | 0.0310 (8) | 0.0327 (8) | 0.0005 (6) | 0.0095 (7) | 0.0034 (6) |
C16 | 0.0328 (8) | 0.0347 (8) | 0.0335 (8) | 0.0011 (6) | 0.0056 (7) | 0.0002 (6) |
C17 | 0.0305 (7) | 0.0361 (9) | 0.0314 (8) | 0.0015 (6) | 0.0014 (7) | 0.0035 (6) |
C18 | 0.0375 (9) | 0.0443 (10) | 0.0373 (9) | 0.0007 (7) | 0.0076 (7) | 0.0035 (7) |
C19 | 0.0449 (10) | 0.0540 (11) | 0.0383 (9) | −0.0073 (8) | 0.0087 (8) | 0.0076 (8) |
C20 | 0.0467 (10) | 0.0422 (10) | 0.0470 (10) | −0.0051 (8) | 0.0039 (9) | 0.0125 (8) |
C21 | 0.0436 (10) | 0.0342 (9) | 0.0529 (11) | 0.0016 (7) | 0.0093 (9) | 0.0037 (8) |
O1—C16 | 1.2332 (18) | C8—C12 | 1.432 (2) |
N1—C16 | 1.3394 (19) | C8—H8 | 0.9500 |
N1—C15 | 1.4587 (19) | C9—C12 | 1.409 (2) |
N1—H1N | 0.863 (19) | C9—C13 | 1.411 (2) |
N2—C21 | 1.330 (2) | C9—C15 | 1.516 (2) |
N2—C17 | 1.342 (2) | C10—C11 | 1.393 (2) |
C1—C2 | 1.359 (2) | C10—C14 | 1.395 (2) |
C1—C13 | 1.422 (2) | C10—H10 | 0.9500 |
C1—H1 | 0.9500 | C11—C12 | 1.435 (2) |
C2—C3 | 1.410 (2) | C13—C14 | 1.440 (2) |
C2—H2 | 0.9500 | C15—H15A | 0.9900 |
C3—C4 | 1.351 (3) | C15—H15B | 0.9900 |
C3—H3 | 0.9500 | C16—C17 | 1.508 (2) |
C4—C14 | 1.431 (2) | C17—C18 | 1.384 (2) |
C4—H4 | 0.9500 | C18—C19 | 1.387 (2) |
C5—C6 | 1.356 (3) | C18—H18 | 0.9500 |
C5—C11 | 1.434 (2) | C19—C20 | 1.382 (3) |
C5—H5 | 0.9500 | C19—H19 | 0.9500 |
C6—C7 | 1.414 (3) | C20—C21 | 1.383 (2) |
C6—H6 | 0.9500 | C20—H20 | 0.9500 |
C7—C8 | 1.364 (3) | C21—H21 | 0.9500 |
C7—H7 | 0.9500 | ||
C16—N1—C15 | 123.97 (13) | C10—C11—C12 | 119.79 (15) |
C16—N1—H1N | 114.7 (11) | C5—C11—C12 | 119.20 (14) |
C15—N1—H1N | 121.4 (11) | C9—C12—C8 | 123.13 (15) |
C21—N2—C17 | 117.21 (14) | C9—C12—C11 | 119.50 (13) |
C2—C1—C13 | 121.42 (16) | C8—C12—C11 | 117.37 (15) |
C2—C1—H1 | 119.3 | C9—C13—C1 | 122.99 (14) |
C13—C1—H1 | 119.3 | C9—C13—C14 | 119.30 (14) |
C1—C2—C3 | 120.57 (16) | C1—C13—C14 | 117.71 (13) |
C1—C2—H2 | 119.7 | C10—C14—C4 | 121.49 (15) |
C3—C2—H2 | 119.7 | C10—C14—C13 | 119.65 (13) |
C4—C3—C2 | 120.69 (14) | C4—C14—C13 | 118.84 (15) |
C4—C3—H3 | 119.7 | N1—C15—C9 | 112.15 (13) |
C2—C3—H3 | 119.7 | N1—C15—H15A | 109.2 |
C3—C4—C14 | 120.73 (16) | C9—C15—H15A | 109.2 |
C3—C4—H4 | 119.6 | N1—C15—H15B | 109.2 |
C14—C4—H4 | 119.6 | C9—C15—H15B | 109.2 |
C6—C5—C11 | 121.12 (17) | H15A—C15—H15B | 107.9 |
C6—C5—H5 | 119.4 | O1—C16—N1 | 124.26 (14) |
C11—C5—H5 | 119.4 | O1—C16—C17 | 121.37 (13) |
C5—C6—C7 | 120.01 (17) | N1—C16—C17 | 114.35 (13) |
C5—C6—H6 | 120.0 | N2—C17—C18 | 123.21 (15) |
C7—C6—H6 | 120.0 | N2—C17—C16 | 116.22 (13) |
C8—C7—C6 | 120.92 (16) | C18—C17—C16 | 120.55 (14) |
C8—C7—H7 | 119.5 | C17—C18—C19 | 118.48 (16) |
C6—C7—H7 | 119.5 | C17—C18—H18 | 120.8 |
C7—C8—C12 | 121.36 (17) | C19—C18—H18 | 120.8 |
C7—C8—H8 | 119.3 | C20—C19—C18 | 118.88 (15) |
C12—C8—H8 | 119.3 | C20—C19—H19 | 120.6 |
C12—C9—C13 | 120.43 (14) | C18—C19—H19 | 120.6 |
C12—C9—C15 | 120.48 (13) | C19—C20—C21 | 118.34 (16) |
C13—C9—C15 | 119.08 (14) | C19—C20—H20 | 120.8 |
C11—C10—C14 | 121.27 (15) | C21—C20—H20 | 120.8 |
C11—C10—H10 | 119.4 | N2—C21—C20 | 123.87 (16) |
C14—C10—H10 | 119.4 | N2—C21—H21 | 118.1 |
C10—C11—C5 | 121.01 (16) | C20—C21—H21 | 118.1 |
C13—C1—C2—C3 | 0.1 (2) | C11—C10—C14—C4 | 179.64 (14) |
C1—C2—C3—C4 | 1.3 (2) | C11—C10—C14—C13 | 1.2 (2) |
C2—C3—C4—C14 | −0.8 (2) | C3—C4—C14—C10 | −179.51 (14) |
C11—C5—C6—C7 | 1.0 (3) | C3—C4—C14—C13 | −1.1 (2) |
C5—C6—C7—C8 | 0.0 (3) | C9—C13—C14—C10 | 1.0 (2) |
C6—C7—C8—C12 | −1.2 (3) | C1—C13—C14—C10 | −179.11 (13) |
C14—C10—C11—C5 | 179.00 (14) | C9—C13—C14—C4 | −177.43 (13) |
C14—C10—C11—C12 | −1.7 (2) | C1—C13—C14—C4 | 2.4 (2) |
C6—C5—C11—C10 | 178.60 (15) | C16—N1—C15—C9 | 120.14 (17) |
C6—C5—C11—C12 | −0.7 (2) | C12—C9—C15—N1 | −93.90 (16) |
C13—C9—C12—C8 | −177.99 (14) | C13—C9—C15—N1 | 86.90 (16) |
C15—C9—C12—C8 | 2.8 (2) | C15—N1—C16—O1 | 3.3 (3) |
C13—C9—C12—C11 | 2.3 (2) | C15—N1—C16—C17 | −175.36 (14) |
C15—C9—C12—C11 | −176.84 (12) | C21—N2—C17—C18 | −0.8 (2) |
C7—C8—C12—C9 | −178.27 (15) | C21—N2—C17—C16 | 177.84 (15) |
C7—C8—C12—C11 | 1.4 (2) | O1—C16—C17—N2 | 176.68 (16) |
C10—C11—C12—C9 | −0.1 (2) | N1—C16—C17—N2 | −4.6 (2) |
C5—C11—C12—C9 | 179.22 (14) | O1—C16—C17—C18 | −4.6 (3) |
C10—C11—C12—C8 | −179.78 (14) | N1—C16—C17—C18 | 174.09 (15) |
C5—C11—C12—C8 | −0.5 (2) | N2—C17—C18—C19 | 1.3 (3) |
C12—C9—C13—C1 | 177.34 (13) | C16—C17—C18—C19 | −177.33 (16) |
C15—C9—C13—C1 | −3.5 (2) | C17—C18—C19—C20 | −0.8 (3) |
C12—C9—C13—C14 | −2.8 (2) | C18—C19—C20—C21 | 0.0 (3) |
C15—C9—C13—C14 | 176.40 (12) | C17—N2—C21—C20 | −0.1 (3) |
C2—C1—C13—C9 | 177.87 (14) | C19—C20—C21—N2 | 0.5 (3) |
C2—C1—C13—C14 | −2.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N2 | 0.865 (17) | 2.193 (18) | 2.655 (2) | 113.1 (15) |
C10—H10···O1i | 0.95 | 2.59 | 3.533 (3) | 170 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C21H16N2O |
Mr | 312.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 153 |
a, b, c (Å) | 10.0182 (3), 8.1082 (3), 19.2442 (6) |
β (°) | 103.070 (1) |
V (Å3) | 1522.70 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.25 × 0.25 × 0.06 |
Data collection | |
Diffractometer | Rigaku RAXIS-RAPID |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14372, 3479, 2304 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.151, 1.01 |
No. of reflections | 3479 |
No. of parameters | 222 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.62, −0.20 |
Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N2 | 0.865 (17) | 2.193 (18) | 2.655 (2) | 113.1 (15) |
C10—H10···O1i | 0.95 | 2.59 | 3.533 (3) | 170.1 |
Symmetry code: (i) x+1, y, z. |
Anthracene is a polycyclic aromatic hydrocarbon that has been widely used as a signaling subunit for both cation (Gunnlaugsson et al., 2003) and anion (Chen & Chen, 2004; Kim & Yoon, 2002) sensing due to its well known photophysical properties and high fluorescence. We here report the crystal structure of the title compound, (I).
In (I) (Fig. 1), the bond lengths and angles are within normal ranges. The anthracene ring system is slightly twisted with a dihedral angle of 1.22 (1)° between the two utmost rings. The anthracene mean plane and pyridin ring make a dihedral angle of 72.6 (1)°. The intramolecular hydrogen bond N1—H1N···N2 (Table 1) influences molecular conformation. The short contact between the anthracene fragments of the neighbouring molecules - C9···C14ii of 3.431 (2) Å and C1···C3iii of 3.591 (2) Å [symmetry codes: (ii) 1 - x, 2 - y,1 - z; (iii) 1 - x, 1 - y, 1 - z] - show an existence of π···π interactions, which form stacks of the molecules parallel to b axis. The crystal packing exhibits also weak intermolecular C—H···O hydrogen bonds.