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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2624.
Published online 2009 October 3. doi:  10.1107/S1600536809039427
PMCID: PMC2971033

2-[1-(9-Anthrylmeth­yl)-1H-pyrazol-3-yl]pyridine

Abstract

The title compound, C23H17N3, can be used in coordination chemistry. The anthracene ring makes dihedral angles of 86.08 (5) and 76.63 (6)°, respectively, with the pyridine and pyrazole rings. The dihedral angle between the pyrazole and pyrimidine rings is 11.79 (7)°. In the structure, weak inter­molecular C—H(...)N hydrogen bonds are observed.

Related literature

For the synthesis, see: Amoroso et al. (1994 [triangle]); Amir et al. (2008 [triangle]); Stell (2005 [triangle]); Ward et al. (2001 [triangle]). For related structures, see: Liu et al. (2008 [triangle]).

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Object name is e-65-o2624-scheme1.jpg

Experimental

Crystal data

  • C23H17N3
  • M r = 335.40
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2624-efi1.jpg
  • a = 13.736 (3) Å
  • b = 13.679 (3) Å
  • c = 8.913 (2) Å
  • β = 98.496 (3)°
  • V = 1656.2 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 93 K
  • 0.40 × 0.33 × 0.20 mm

Data collection

  • Rigaku SPIDER diffractometer
  • Absorption correction: none
  • 13094 measured reflections
  • 3777 independent reflections
  • 3156 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.122
  • S = 1.00
  • 3777 reflections
  • 235 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039427/at2873sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039427/at2873Isup2.hkl

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

Acknowledgments

The authors thank the Scientific Research Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of the Sichuan Education Department (grant No. 2006B039).

supplementary crystallographic information

Comment

In recent years, scientists have paid much attention to the synthetic approach and the structural control of coordination architectures with ligands based on pyrazolyl-pyridine chelating units. (Stell, 2005; Ward et al., 2001). In addition, some pyrazole-derived ligands are useful in medication. (Amir et al., 2008). We report herein the synthesis and crystal structure of the title compound (I). Bond lengths and angles in (I) (Fig. 1) are normal.

The dihedral angles formed by the anthracene ring between pyridine and the pyrazole rings are 86.08 (5)° and 76.63 (6)°, respectively. Pyrazole makes a dihedral angle of 11.79 (7)° with pyridine ring .

Weak intermolecular C—H···N hydrogen bonds between molecules are observed.

Experimental

The title compound was prepared according to the reported procedure of Amoroso et al. (1994). Yellow single crystals suitable for X-ray diffraction were obtained by recrystallization from dichloromethane and pPetroleum ether.

Refinement

H atoms were placed in calculated positions with C—H = 0.95–0.9900 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

Crystal data

C23H17N3F(000) = 704
Mr = 335.40Dx = 1.345 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4717 reflections
a = 13.736 (3) Åθ = 3.3–27.5°
b = 13.679 (3) ŵ = 0.08 mm1
c = 8.913 (2) ÅT = 93 K
β = 98.496 (3)°Prism, yellow
V = 1656.2 (7) Å30.40 × 0.33 × 0.20 mm
Z = 4

Data collection

Rigaku SPIDER diffractometer3156 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.034
graphiteθmax = 27.5°, θmin = 3.3°
ω scansh = −17→17
13094 measured reflectionsk = −17→15
3777 independent reflectionsl = −11→11

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0596P)2 + 0.333P] where P = (Fo2 + 2Fc2)/3
3777 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.22 e Å3

Special details

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)

xyzUiso*/Ueq
N10.25794 (8)0.55924 (8)0.72942 (13)0.0216 (3)
N20.22498 (8)0.64246 (8)0.78636 (13)0.0219 (3)
N30.02717 (8)0.65643 (9)1.01184 (13)0.0264 (3)
C10.46616 (10)0.43366 (9)0.66749 (15)0.0216 (3)
C20.51916 (10)0.47480 (11)0.80358 (16)0.0280 (3)
H20.49360.53090.84690.034*
C30.60559 (11)0.43505 (11)0.87224 (17)0.0313 (4)
H30.63920.46400.96210.038*
C40.64588 (11)0.35107 (11)0.81111 (17)0.0308 (3)
H40.70640.32450.85950.037*
C50.59810 (10)0.30887 (11)0.68378 (16)0.0270 (3)
H50.62560.25260.64370.032*
C60.50709 (10)0.34731 (10)0.60844 (15)0.0229 (3)
C70.45791 (10)0.30295 (10)0.47849 (16)0.0241 (3)
H70.48480.24530.44140.029*
C80.37068 (10)0.34050 (10)0.40140 (15)0.0235 (3)
C90.32166 (11)0.29600 (11)0.26587 (17)0.0311 (3)
H90.34730.23730.23040.037*
C100.23940 (12)0.33579 (13)0.18707 (18)0.0375 (4)
H100.20840.30530.09670.045*
C110.19940 (11)0.42289 (12)0.23918 (17)0.0341 (4)
H110.14210.45100.18280.041*
C120.24260 (10)0.46640 (11)0.36920 (16)0.0282 (3)
H120.21380.52380.40340.034*
C130.33022 (10)0.42817 (10)0.45598 (15)0.0221 (3)
C140.37813 (10)0.47367 (10)0.58909 (15)0.0219 (3)
C150.33882 (10)0.56910 (10)0.63969 (17)0.0255 (3)
H15A0.39340.60500.70080.031*
H15B0.31570.60900.54880.031*
C160.20496 (10)0.48050 (10)0.76085 (16)0.0247 (3)
H160.21460.41490.73140.030*
C170.13437 (10)0.51320 (10)0.84353 (16)0.0251 (3)
H170.08590.47550.88320.030*
C180.14980 (9)0.61436 (10)0.85633 (14)0.0209 (3)
C190.09372 (9)0.68884 (10)0.92693 (15)0.0217 (3)
C200.10796 (10)0.78813 (11)0.90066 (17)0.0282 (3)
H200.15650.80870.84190.034*
C210.05025 (11)0.85594 (11)0.96156 (18)0.0322 (4)
H210.05780.92380.94390.039*
C22−0.01841 (10)0.82348 (11)1.04831 (17)0.0299 (3)
H22−0.05920.86841.09140.036*
C23−0.02639 (10)0.72459 (11)1.07094 (17)0.0289 (3)
H23−0.07300.70301.13260.035*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0219 (6)0.0206 (6)0.0242 (6)0.0015 (4)0.0092 (5)−0.0014 (5)
N20.0204 (6)0.0214 (6)0.0252 (6)0.0009 (4)0.0069 (5)−0.0031 (4)
N30.0232 (6)0.0312 (7)0.0264 (6)0.0013 (5)0.0092 (5)−0.0025 (5)
C10.0219 (7)0.0223 (7)0.0229 (7)−0.0025 (5)0.0104 (5)0.0026 (5)
C20.0295 (8)0.0317 (8)0.0247 (7)−0.0045 (6)0.0107 (6)−0.0008 (6)
C30.0284 (7)0.0422 (9)0.0239 (7)−0.0092 (6)0.0056 (6)0.0022 (6)
C40.0225 (7)0.0422 (9)0.0285 (8)0.0003 (6)0.0066 (6)0.0119 (6)
C50.0240 (7)0.0290 (8)0.0299 (8)0.0032 (6)0.0106 (6)0.0086 (6)
C60.0226 (7)0.0238 (7)0.0248 (7)0.0013 (5)0.0117 (6)0.0055 (5)
C70.0255 (7)0.0208 (7)0.0285 (7)0.0009 (5)0.0122 (6)−0.0005 (5)
C80.0238 (7)0.0246 (7)0.0246 (7)−0.0030 (5)0.0114 (6)−0.0013 (6)
C90.0298 (8)0.0344 (8)0.0314 (8)−0.0049 (6)0.0121 (6)−0.0075 (6)
C100.0301 (8)0.0536 (11)0.0292 (8)−0.0096 (7)0.0059 (7)−0.0061 (7)
C110.0218 (7)0.0521 (10)0.0289 (8)−0.0026 (7)0.0052 (6)0.0086 (7)
C120.0223 (7)0.0332 (8)0.0308 (8)0.0006 (6)0.0094 (6)0.0065 (6)
C130.0207 (6)0.0237 (7)0.0241 (7)−0.0012 (5)0.0105 (5)0.0034 (5)
C140.0219 (6)0.0212 (7)0.0250 (7)0.0000 (5)0.0114 (5)0.0019 (5)
C150.0254 (7)0.0234 (7)0.0312 (7)0.0010 (5)0.0153 (6)0.0006 (6)
C160.0270 (7)0.0203 (7)0.0286 (7)−0.0011 (5)0.0100 (6)−0.0002 (6)
C170.0238 (7)0.0253 (7)0.0279 (7)−0.0007 (5)0.0094 (6)0.0015 (6)
C180.0194 (6)0.0250 (7)0.0185 (6)0.0008 (5)0.0035 (5)−0.0004 (5)
C190.0179 (6)0.0266 (7)0.0205 (6)0.0010 (5)0.0021 (5)−0.0033 (5)
C200.0226 (7)0.0282 (8)0.0350 (8)−0.0020 (6)0.0082 (6)−0.0058 (6)
C210.0279 (8)0.0271 (8)0.0429 (9)−0.0007 (6)0.0092 (7)−0.0080 (6)
C220.0224 (7)0.0318 (8)0.0362 (8)0.0033 (6)0.0072 (6)−0.0096 (7)
C230.0233 (7)0.0368 (9)0.0281 (7)0.0014 (6)0.0090 (6)−0.0061 (6)

Geometric parameters (Å, °)

N1—N21.3513 (15)C10—C111.419 (2)
N1—C161.3522 (17)C10—H100.9500
N1—C151.4678 (17)C11—C121.359 (2)
N2—C181.3391 (17)C11—H110.9500
N3—C231.3425 (18)C12—C131.4301 (19)
N3—C191.3451 (17)C12—H120.9500
C1—C141.4144 (19)C13—C141.4132 (19)
C1—C21.4342 (19)C14—C151.5069 (19)
C1—C61.4407 (19)C15—H15A0.9900
C2—C31.366 (2)C15—H15B0.9900
C2—H20.9500C16—C171.3764 (18)
C3—C41.418 (2)C16—H160.9500
C3—H30.9500C17—C181.402 (2)
C4—C51.353 (2)C17—H170.9500
C4—H40.9500C18—C191.4733 (18)
C5—C61.4290 (19)C19—C201.397 (2)
C5—H50.9500C20—C211.382 (2)
C6—C71.391 (2)C20—H200.9500
C7—C81.389 (2)C21—C221.378 (2)
C7—H70.9500C21—H210.9500
C8—C91.429 (2)C22—C231.374 (2)
C8—C131.4365 (19)C22—H220.9500
C9—C101.353 (2)C23—H230.9500
C9—H90.9500
N2—N1—C16111.88 (11)C11—C12—H12119.1
N2—N1—C15116.73 (11)C13—C12—H12119.1
C16—N1—C15131.29 (11)C14—C13—C12122.90 (13)
C18—N2—N1104.91 (11)C14—C13—C8119.77 (12)
C23—N3—C19116.69 (13)C12—C13—C8117.32 (13)
C14—C1—C2123.78 (13)C13—C14—C1120.16 (12)
C14—C1—C6119.21 (12)C13—C14—C15119.33 (12)
C2—C1—C6117.00 (12)C1—C14—C15120.35 (12)
C3—C2—C1121.45 (14)N1—C15—C14114.65 (11)
C3—C2—H2119.3N1—C15—H15A108.6
C1—C2—H2119.3C14—C15—H15A108.6
C2—C3—C4120.87 (14)N1—C15—H15B108.6
C2—C3—H3119.6C14—C15—H15B108.6
C4—C3—H3119.6H15A—C15—H15B107.6
C5—C4—C3119.94 (14)N1—C16—C17107.18 (12)
C5—C4—H4120.0N1—C16—H16126.4
C3—C4—H4120.0C17—C16—H16126.4
C4—C5—C6121.28 (14)C16—C17—C18104.73 (12)
C4—C5—H5119.4C16—C17—H17127.6
C6—C5—H5119.4C18—C17—H17127.6
C7—C6—C5120.94 (13)N2—C18—C17111.30 (11)
C7—C6—C1119.61 (12)N2—C18—C19119.23 (12)
C5—C6—C1119.44 (13)C17—C18—C19129.41 (12)
C8—C7—C6121.87 (13)N3—C19—C20122.57 (12)
C8—C7—H7119.1N3—C19—C18117.01 (12)
C6—C7—H7119.1C20—C19—C18120.38 (12)
C7—C8—C9121.67 (13)C21—C20—C19118.95 (13)
C7—C8—C13119.34 (13)C21—C20—H20120.5
C9—C8—C13118.95 (13)C19—C20—H20120.5
C10—C9—C8121.36 (14)C22—C21—C20118.93 (14)
C10—C9—H9119.3C22—C21—H21120.5
C8—C9—H9119.3C20—C21—H21120.5
C9—C10—C11120.12 (14)C23—C22—C21118.39 (13)
C9—C10—H10119.9C23—C22—H22120.8
C11—C10—H10119.9C21—C22—H22120.8
C12—C11—C10120.38 (14)N3—C23—C22124.45 (14)
C12—C11—H11119.8N3—C23—H23117.8
C10—C11—H11119.8C22—C23—H23117.8
C11—C12—C13121.85 (14)
C16—N1—N2—C180.52 (15)C12—C13—C14—C15−2.84 (19)
C15—N1—N2—C18177.37 (11)C8—C13—C14—C15176.04 (11)
C14—C1—C2—C3−177.87 (13)C2—C1—C14—C13−179.68 (12)
C6—C1—C2—C31.33 (19)C6—C1—C14—C131.14 (19)
C1—C2—C3—C4−0.2 (2)C2—C1—C14—C155.00 (19)
C2—C3—C4—C5−0.6 (2)C6—C1—C14—C15−174.18 (11)
C3—C4—C5—C60.1 (2)N2—N1—C15—C14175.47 (11)
C4—C5—C6—C7−179.35 (13)C16—N1—C15—C14−8.4 (2)
C4—C5—C6—C11.1 (2)C13—C14—C15—N183.96 (15)
C14—C1—C6—C7−2.08 (19)C1—C14—C15—N1−100.67 (15)
C2—C1—C6—C7178.69 (12)N2—N1—C16—C17−0.56 (16)
C14—C1—C6—C5177.49 (11)C15—N1—C16—C17−176.82 (13)
C2—C1—C6—C5−1.75 (18)N1—C16—C17—C180.35 (15)
C5—C6—C7—C8−178.37 (12)N1—N2—C18—C17−0.28 (15)
C1—C6—C7—C81.2 (2)N1—N2—C18—C19−177.62 (11)
C6—C7—C8—C9178.47 (12)C16—C17—C18—N2−0.04 (15)
C6—C7—C8—C130.6 (2)C16—C17—C18—C19176.95 (13)
C7—C8—C9—C10−176.59 (14)C23—N3—C19—C200.30 (19)
C13—C8—C9—C101.3 (2)C23—N3—C19—C18−177.46 (12)
C8—C9—C10—C11−0.6 (2)N2—C18—C19—N3−171.91 (12)
C9—C10—C11—C12−0.7 (2)C17—C18—C19—N311.3 (2)
C10—C11—C12—C131.5 (2)N2—C18—C19—C2010.27 (19)
C11—C12—C13—C14178.08 (13)C17—C18—C19—C20−166.52 (14)
C11—C12—C13—C8−0.8 (2)N3—C19—C20—C21−1.3 (2)
C7—C8—C13—C14−1.57 (19)C18—C19—C20—C21176.38 (13)
C9—C8—C13—C14−179.47 (12)C19—C20—C21—C221.0 (2)
C7—C8—C13—C12177.37 (12)C20—C21—C22—C230.2 (2)
C9—C8—C13—C12−0.53 (18)C19—N3—C23—C221.0 (2)
C12—C13—C14—C1−178.22 (12)C21—C22—C23—N3−1.3 (2)
C8—C13—C14—C10.66 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···N2i0.952.553.312 (2)138

Symmetry codes: (i) −x+1, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2873).

References

  • Amir, M., Kumar, H. & Khan, S. A. (2008). Bioorg. Med. Chem. Lett.18, 918–922. [PubMed]
  • Amoroso, A. J., Cargill Thompson, A. M., Jeffery, J. C., Jones, P. L., McCleverty, J. A. & Ward, M. D. (1994). J. Chem. Soc. Chem. Commun. pp. 2751–2752.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Liu, C.-S., Sun, G.-H. & Guo, L.-Q. (2008). Acta Cryst. E64, m69. [PMC free article] [PubMed]
  • Rigaku/MSC (2004). RAPID-AUTO and CrystalStructure Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stell, P. J. (2005). Acc. Chem. Res.38, 243–250. [PubMed]
  • Ward, M. D., McCleverty, J. A. & Jeffery, J. C. (2001). Coord. Chem. Rev.222, 251–272.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography