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In the title mol­ecule, C21H16N2O, the anthracene ring system is slightly twisted with a dihedral angle of 1.22 (1)° between the two outermost rings. The anthracene mean plane and pyridine ring make a dihedral angle of 72.6 (1)°. The π...π inter­actions [3.551 (2) Å] between the anthracene fragments form stacks of mol­ecules parallel to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026918/cv2255sup1.cif
Contains datablocks y2312, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026918/cv2255Isup2.hkl
Contains datablock I

CCDC reference: 654949

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](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

Comment top

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.

Related literature top

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).

Experimental top

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.

Refinement top

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.

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atomic numbering.
N-(anthracen-10-ylmethyl)picolinamide top
Crystal data top
C21H16N2OF(000) = 656
Mr = 312.36Dx = 1.363 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9693 reflections
a = 10.0182 (3) Åθ = 3.2–27.5°
b = 8.1082 (3) ŵ = 0.09 mm1
c = 19.2442 (6) ÅT = 153 K
β = 103.070 (1)°Block, yellow
V = 1522.70 (9) Å30.25 × 0.25 × 0.06 mm
Z = 4
Data collection top
Rigaku RAXIS-RAPID
diffractometer
2304 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 27.5°, θmin = 3.3°
ω scansh = 1213
14372 measured reflectionsk = 1010
3479 independent reflectionsl = 2424
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H 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 reflectionsΔρmax = 0.62 e Å3
222 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.013 (3)
Crystal data top
C21H16N2OV = 1522.70 (9) Å3
Mr = 312.36Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.0182 (3) ŵ = 0.09 mm1
b = 8.1082 (3) ÅT = 153 K
c = 19.2442 (6) Å0.25 × 0.25 × 0.06 mm
β = 103.070 (1)°
Data collection top
Rigaku RAXIS-RAPID
diffractometer
2304 reflections with I > 2σ(I)
14372 measured reflectionsRint = 0.032
3479 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.62 e Å3
3479 reflectionsΔρmin = 0.20 e Å3
222 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
xyzUiso*/Ueq
O10.03419 (13)0.86927 (15)0.62684 (7)0.0469 (4)
N10.16317 (14)0.73494 (17)0.56145 (7)0.0346 (3)
N20.07086 (15)0.44338 (17)0.59240 (8)0.0389 (4)
C10.39511 (17)0.70846 (19)0.45469 (8)0.0355 (4)
H10.29790.70490.44100.043*
C20.46983 (18)0.6366 (2)0.41213 (9)0.0392 (4)
H20.42440.58390.36920.047*
C30.61427 (18)0.6397 (2)0.43115 (9)0.0391 (4)
H30.66520.59100.40040.047*
C40.68103 (18)0.71105 (19)0.49267 (9)0.0378 (4)
H40.77840.71080.50500.045*
C50.67089 (19)1.0119 (2)0.71376 (9)0.0426 (4)
H50.76811.00850.72720.051*
C60.6004 (2)1.0877 (2)0.75709 (10)0.0480 (5)
H60.64831.13820.80010.058*
C70.4556 (2)1.0915 (2)0.73833 (9)0.0458 (5)
H70.40681.14480.76900.055*
C80.38483 (19)1.0198 (2)0.67683 (9)0.0396 (4)
H80.28751.02220.66590.048*
C90.38519 (16)0.86933 (18)0.56359 (8)0.0316 (4)
C100.67400 (17)0.86240 (19)0.60291 (9)0.0351 (4)
H100.77130.86280.61560.042*
C110.60121 (17)0.93700 (19)0.64807 (8)0.0345 (4)
C120.45425 (17)0.94096 (18)0.62850 (8)0.0326 (4)
C130.45931 (15)0.78882 (17)0.51927 (8)0.0298 (3)
C140.60675 (16)0.78706 (18)0.53946 (8)0.0324 (4)
C150.23042 (16)0.87963 (19)0.53993 (9)0.0343 (4)
H15A0.19820.97950.56080.041*
H15B0.20420.89040.48740.041*
C160.07404 (16)0.74078 (19)0.60383 (9)0.0340 (4)
C170.02651 (16)0.5742 (2)0.62342 (8)0.0336 (4)
C180.05583 (17)0.5611 (2)0.67204 (9)0.0398 (4)
H180.08670.65680.69220.048*
C190.09223 (19)0.4049 (2)0.69066 (10)0.0459 (4)
H190.14760.39160.72430.055*
C200.04654 (19)0.2690 (2)0.65940 (10)0.0463 (4)
H200.06980.16050.67110.056*
C210.03386 (18)0.2950 (2)0.61073 (10)0.0438 (4)
H210.06450.20120.58910.053*
H1N0.1791 (18)0.637 (2)0.5475 (10)0.040 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0505 (7)0.0364 (7)0.0597 (8)0.0007 (5)0.0252 (7)0.0038 (6)
N10.0384 (7)0.0304 (7)0.0360 (7)0.0010 (6)0.0104 (6)0.0006 (6)
N20.0381 (7)0.0342 (7)0.0443 (8)0.0013 (6)0.0096 (6)0.0027 (6)
C10.0410 (9)0.0327 (8)0.0318 (8)0.0006 (7)0.0060 (7)0.0019 (6)
C20.0525 (10)0.0330 (9)0.0329 (9)0.0006 (7)0.0112 (8)0.0018 (7)
C30.0517 (10)0.0321 (8)0.0378 (9)0.0073 (7)0.0188 (8)0.0035 (7)
C40.0419 (9)0.0314 (8)0.0422 (9)0.0037 (7)0.0140 (8)0.0075 (7)
C50.0509 (10)0.0377 (9)0.0358 (9)0.0104 (8)0.0028 (8)0.0047 (7)
C60.0688 (13)0.0386 (10)0.0321 (9)0.0098 (9)0.0024 (9)0.0012 (7)
C70.0735 (13)0.0332 (9)0.0328 (9)0.0015 (9)0.0162 (9)0.0004 (7)
C80.0547 (10)0.0318 (8)0.0339 (9)0.0015 (7)0.0130 (8)0.0038 (7)
C90.0376 (8)0.0269 (7)0.0307 (8)0.0021 (6)0.0088 (7)0.0054 (6)
C100.0360 (8)0.0320 (8)0.0358 (9)0.0036 (6)0.0052 (7)0.0081 (7)
C110.0441 (9)0.0281 (8)0.0298 (8)0.0064 (6)0.0051 (7)0.0056 (6)
C120.0454 (9)0.0248 (7)0.0287 (8)0.0013 (6)0.0106 (7)0.0048 (6)
C130.0351 (8)0.0252 (7)0.0294 (8)0.0007 (6)0.0080 (7)0.0036 (6)
C140.0380 (9)0.0260 (7)0.0342 (8)0.0005 (6)0.0103 (7)0.0073 (6)
C150.0398 (8)0.0310 (8)0.0327 (8)0.0005 (6)0.0095 (7)0.0034 (6)
C160.0328 (8)0.0347 (8)0.0335 (8)0.0011 (6)0.0056 (7)0.0002 (6)
C170.0305 (7)0.0361 (9)0.0314 (8)0.0015 (6)0.0014 (7)0.0035 (6)
C180.0375 (9)0.0443 (10)0.0373 (9)0.0007 (7)0.0076 (7)0.0035 (7)
C190.0449 (10)0.0540 (11)0.0383 (9)0.0073 (8)0.0087 (8)0.0076 (8)
C200.0467 (10)0.0422 (10)0.0470 (10)0.0051 (8)0.0039 (9)0.0125 (8)
C210.0436 (10)0.0342 (9)0.0529 (11)0.0016 (7)0.0093 (9)0.0037 (8)
Geometric parameters (Å, º) top
O1—C161.2332 (18)C8—C121.432 (2)
N1—C161.3394 (19)C8—H80.9500
N1—C151.4587 (19)C9—C121.409 (2)
N1—H1N0.863 (19)C9—C131.411 (2)
N2—C211.330 (2)C9—C151.516 (2)
N2—C171.342 (2)C10—C111.393 (2)
C1—C21.359 (2)C10—C141.395 (2)
C1—C131.422 (2)C10—H100.9500
C1—H10.9500C11—C121.435 (2)
C2—C31.410 (2)C13—C141.440 (2)
C2—H20.9500C15—H15A0.9900
C3—C41.351 (3)C15—H15B0.9900
C3—H30.9500C16—C171.508 (2)
C4—C141.431 (2)C17—C181.384 (2)
C4—H40.9500C18—C191.387 (2)
C5—C61.356 (3)C18—H180.9500
C5—C111.434 (2)C19—C201.382 (3)
C5—H50.9500C19—H190.9500
C6—C71.414 (3)C20—C211.383 (2)
C6—H60.9500C20—H200.9500
C7—C81.364 (3)C21—H210.9500
C7—H70.9500
C16—N1—C15123.97 (13)C10—C11—C12119.79 (15)
C16—N1—H1N114.7 (11)C5—C11—C12119.20 (14)
C15—N1—H1N121.4 (11)C9—C12—C8123.13 (15)
C21—N2—C17117.21 (14)C9—C12—C11119.50 (13)
C2—C1—C13121.42 (16)C8—C12—C11117.37 (15)
C2—C1—H1119.3C9—C13—C1122.99 (14)
C13—C1—H1119.3C9—C13—C14119.30 (14)
C1—C2—C3120.57 (16)C1—C13—C14117.71 (13)
C1—C2—H2119.7C10—C14—C4121.49 (15)
C3—C2—H2119.7C10—C14—C13119.65 (13)
C4—C3—C2120.69 (14)C4—C14—C13118.84 (15)
C4—C3—H3119.7N1—C15—C9112.15 (13)
C2—C3—H3119.7N1—C15—H15A109.2
C3—C4—C14120.73 (16)C9—C15—H15A109.2
C3—C4—H4119.6N1—C15—H15B109.2
C14—C4—H4119.6C9—C15—H15B109.2
C6—C5—C11121.12 (17)H15A—C15—H15B107.9
C6—C5—H5119.4O1—C16—N1124.26 (14)
C11—C5—H5119.4O1—C16—C17121.37 (13)
C5—C6—C7120.01 (17)N1—C16—C17114.35 (13)
C5—C6—H6120.0N2—C17—C18123.21 (15)
C7—C6—H6120.0N2—C17—C16116.22 (13)
C8—C7—C6120.92 (16)C18—C17—C16120.55 (14)
C8—C7—H7119.5C17—C18—C19118.48 (16)
C6—C7—H7119.5C17—C18—H18120.8
C7—C8—C12121.36 (17)C19—C18—H18120.8
C7—C8—H8119.3C20—C19—C18118.88 (15)
C12—C8—H8119.3C20—C19—H19120.6
C12—C9—C13120.43 (14)C18—C19—H19120.6
C12—C9—C15120.48 (13)C19—C20—C21118.34 (16)
C13—C9—C15119.08 (14)C19—C20—H20120.8
C11—C10—C14121.27 (15)C21—C20—H20120.8
C11—C10—H10119.4N2—C21—C20123.87 (16)
C14—C10—H10119.4N2—C21—H21118.1
C10—C11—C5121.01 (16)C20—C21—H21118.1
C13—C1—C2—C30.1 (2)C11—C10—C14—C4179.64 (14)
C1—C2—C3—C41.3 (2)C11—C10—C14—C131.2 (2)
C2—C3—C4—C140.8 (2)C3—C4—C14—C10179.51 (14)
C11—C5—C6—C71.0 (3)C3—C4—C14—C131.1 (2)
C5—C6—C7—C80.0 (3)C9—C13—C14—C101.0 (2)
C6—C7—C8—C121.2 (3)C1—C13—C14—C10179.11 (13)
C14—C10—C11—C5179.00 (14)C9—C13—C14—C4177.43 (13)
C14—C10—C11—C121.7 (2)C1—C13—C14—C42.4 (2)
C6—C5—C11—C10178.60 (15)C16—N1—C15—C9120.14 (17)
C6—C5—C11—C120.7 (2)C12—C9—C15—N193.90 (16)
C13—C9—C12—C8177.99 (14)C13—C9—C15—N186.90 (16)
C15—C9—C12—C82.8 (2)C15—N1—C16—O13.3 (3)
C13—C9—C12—C112.3 (2)C15—N1—C16—C17175.36 (14)
C15—C9—C12—C11176.84 (12)C21—N2—C17—C180.8 (2)
C7—C8—C12—C9178.27 (15)C21—N2—C17—C16177.84 (15)
C7—C8—C12—C111.4 (2)O1—C16—C17—N2176.68 (16)
C10—C11—C12—C90.1 (2)N1—C16—C17—N24.6 (2)
C5—C11—C12—C9179.22 (14)O1—C16—C17—C184.6 (3)
C10—C11—C12—C8179.78 (14)N1—C16—C17—C18174.09 (15)
C5—C11—C12—C80.5 (2)N2—C17—C18—C191.3 (3)
C12—C9—C13—C1177.34 (13)C16—C17—C18—C19177.33 (16)
C15—C9—C13—C13.5 (2)C17—C18—C19—C200.8 (3)
C12—C9—C13—C142.8 (2)C18—C19—C20—C210.0 (3)
C15—C9—C13—C14176.40 (12)C17—N2—C21—C200.1 (3)
C2—C1—C13—C9177.87 (14)C19—C20—C21—N20.5 (3)
C2—C1—C13—C142.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N20.865 (17)2.193 (18)2.655 (2)113.1 (15)
C10—H10···O1i0.952.593.533 (3)170
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC21H16N2O
Mr312.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)153
a, b, c (Å)10.0182 (3), 8.1082 (3), 19.2442 (6)
β (°) 103.070 (1)
V3)1522.70 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.25 × 0.25 × 0.06
Data collection
DiffractometerRigaku RAXIS-RAPID
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
14372, 3479, 2304
Rint0.032
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.151, 1.01
No. of reflections3479
No. of parameters222
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N20.865 (17)2.193 (18)2.655 (2)113.1 (15)
C10—H10···O1i0.952.593.533 (3)170.1
Symmetry code: (i) x+1, y, z.
 

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