5,6 Di­phenyl 3 (pyrazin 2 yl) 1,2,4 triazine

Acta Cryst.(2002). E58, o1321±o1322 DOI: 10.1107/S1600536802019591 Deng Honget al. C₁₉H₁₃N₅

o1321

organic papers

Acta Crystallographica Section E Structure Reports

Online

ISSN 1600-5368

5,6-Diphenyl-3-(pyrazin-2-yl)-1,2,4-triazine

Hong Deng, Chunlong Chen, Hao Zhang, Chengyong Su and Liangnian Ji*

School of Chemistry and Chemical Engineering, Zhongshan University, Guangzhou 510275, People's Republic of China

Correspondence e-mail: cep00ccl@student.zsu.edu.cn

Key indicators Single-crystal X-ray study

T= 293 K

Mean(C±C) = 0.002 AÊ

Rfactor = 0.039

wRfactor = 0.108

Data-to-parameter ratio = 15.1

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2002 International Union of Crystallography Printed in Great Britain ± all rights reserved

The title compound, C38H26N10, has been structurally

characterized. The molecule contains two heterocycles that are almost coplanar.

Comment

Ruthenium(II) polypyridyl complexes have aroused intense interest because of their extensive applications in the ®elds of photochemistry, photophysics, photocatalysis, electro-chemistry and bioelectro-chemistry. In particular, their important applications for DNA binding, electrochemical luminescence and solar-energy battery materials are well known (Juriset al., 1988; Krausz & Riesen, 1997; MacDonnell et al., 1999). The interactions of polypyridylruthenium complexes with DNA have been well documented (Barton & Lolis, 1985; Barton, 1986; Ambroize & Maiya, 2000). In our group, we have focused our interest on an investigation of the mechanism of their interaction with DNA; many new substituted derivatives of the ligands of ruthenium(II) polypyridyl complexes have been designed and synthesized (Liuet al., 2001; Xiong & Ji, 1999; Jiet al., 2001; Wuet al., 1997). However, it is noteworthy that most of these ligands are symmetric and that the use of asymmetric ligands for coordination is rare. We are interested in the investigation of polypyridylruthenium(II) complexes with asymmetric ligands as DNA binding reagents. In this report, we discuss the crystal structure analysis of the asym-metric ligand 5,6-diphenyl-3-(pyrazin-2-yl)-1,2,4-triazine, (I).

The CÐN distances show no remarkable features, with values in the range 1.326 (2)±1.344 (2) AÊ, which are shorter than the single-bond length of 1.480 AÊ and longer than the typical C N distance of 1.280 AÊ, indicating partial double-bond character and suggesting conjugation in the heterocycle. The C6ÐC8, C4ÐC5 and C7ÐC14 bond lengths are all close to the standard values for single bonds between trigonally linked C atoms (Cruickshank & Spark, 1960). The two heterocycles in the solid structure are almost coplanar, with a dihedral angle of 1.97 (8)_.

Experimental

The title compound was synthesized using the method described in the literature (Case, 1968). The single crystal used for X-ray analysis was recrystallized from ethanol. Elemental analysis calculated for C19H13N5(%): C 73.31, H 4.18, N 22.51; found: 73.06, H 4.31, N 22.38.

Crystal data

C19H13N5

Mr= 311.34 Monoclinic, P21=n

a= 14.294 (7) AÊ

b= 7.027 (4) AÊ

c= 15.679 (8) AÊ = 105.149 (9)

V= 1520.2 (13) AÊ3

Z= 4

Dx= 1.360 Mg mÿ3 MoKradiation Cell parameters from 4369

re¯ections = 1.7±27.1

= 0.09 mmÿ1

T= 293 (2) K Block, yellow 0.500.300.28 mm

Data collection

Bruker SMART CCD diffractometer 'and!scans

Absorption correction: multi-scan (Blessing, 1995)

Tmin= 0.959,Tmax= 0.977

9062 measured re¯ections

3290 independent re¯ections 2397 re¯ections withI> 2(I)

Rint= 0.022

max= 27.1

h=ÿ18!18

k=ÿ8!8

l=ÿ13!20

Re®nement

Re®nement onF2

R[F2_{> 2(F}2_{)] = 0.039}

wR(F2_{) = 0.108}

S= 1.04 3290 re¯ections 218 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0409P)2 + 0.3681P]

whereP= (Fo2+ 2Fc2)/3 (/)max= 0.001

max= 0.15 e AÊÿ3

min=ÿ0.15 e AÊÿ3

Extinction correction:SHELXL97 Extinction coef®cient: 0.0224 (17)

Table 1

Selected geometric parameters (AÊ).

N1ÐC1 1.334 (2) N1ÐC4 1.337 (2) N2ÐC3 1.328 (2) N2ÐC2 1.331 (2) N3ÐC5 1.333 (2) N4ÐC6 1.339 (2)

N5ÐC7 1.327 (2) N5ÐC5 1.344 (2) C4ÐC5 1.489 (2) C6ÐC8 1.481 (2) C7ÐC14 1.489 (2)

H atoms were placed in calculated positions and re®ned using a riding model.

Data collection:SMART(Bruker, 1998); cell re®nement:SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure:SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication:SHELXTL.

We are grateful to the National Natural Science Foundation of China, the Natural Science Foundation of Guangdong Province, the State Key Laboratory of Coordination Chem-istry in Nanjing University and the Research Fund of the Royal Society of Chemistry, UK, for ®nancial support.

References

Ambroize, A. & Maiya, B. G. (2000).Inorg. Chem.39, 4264±4272. Barton, J. K. (1986).Science,233, 727±734.

Barton, J. K. & Lolis, E. (1985).J. Am. Chem. Soc.107, 708±709. Blessing, R. H. (1995).Acta Cryst.A51, 33±38.

Bruker (1998).SMART(Version 5.0) andSHELXTL(Version 5.1). Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (1999).SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Case, F. H. (1968).J. Heterocycl. Chem.5, 223±226.

Cruickshank, D. W. J. & Spark, R. A. (1960).Proc. R. Soc. A,258, 270±285. Ji, L. N. Zou, X. H. & Liu, J. G. (2001).Coord. Chem. Rev.216, 513±536. Juris, A., Balzani, V., Barigelletti, F., Campagna, S., Belser, P. & von Zelewsky,

A. (1988).Coord. Chem. Rev.84, 85±277.

Krausz, E. & Riesen, H. (1997).Coord. Chem. Rev.159, 9±40.

Liu, J. G., Zhang, Q. L., Shi, X. F. & Ji, L. N. (2001).Inorg. Chem.40, 5045± 5050.

MacDonnell, F. M., Kim, M. J. & Bodige, S. (1999).Coord. Chem. Rev.186, 535±549.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.

Wu, J. Z., Ye, B. H., Wang, L., Ji, L. N., Zhou, J. Y., Li, R. H. & Zhou, Z. Y. (1997).J. Chem. Soc. Dalton Trans.pp. 1395±1401.

Xiong, Y. & Ji, L. N. (1999).Coord. Chem. Rev.186, 711±733.

Figure 1

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sup-1 Acta Cryst. (2002). E58, o1321–o1322

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Acta Cryst. (2002). E58, o1321–o1322 [https://doi.org/10.1107/S1600536802019591]

5,6-Diphenyl-3-(pyrazin-2-yl)-1,2,4-triazine

Hong Deng, Chunlong Chen, Hao Zhang, Chengyong Su and Liangnian Ji

5,6-Diphenyl-3-(pyrazin-2-yl)-1,2,4-triazine

Crystal data C19H13N5

Mr = 311.34 Monoclinic, P21/n

a = 14.294 (7) Å b = 7.027 (4) Å c = 15.679 (8) Å β = 105.149 (9)° V = 1520.2 (13) Å3

Z = 4

F(000) = 648 Dx = 1.360 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 4369 reflections θ = 1.7–27.1°

µ = 0.09 mm−1

T = 293 K Block, yellow

0.50 × 0.30 × 0.28 mm

Data collection Bruker SMART CCD

diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

φ and ω scans

Absorption correction: empirical (using intensity measurements)

(Blessing, 1995) Tmin = 0.959, Tmax = 0.977

9062 measured reflections 3290 independent reflections 2397 reflections with I > 2σ(I) Rint = 0.022

θmax = 27.1°, θmin = 1.7°

h = −18→18 k = −8→8 l = −13→20

Refinement Refinement on F2

Least-squares matrix: full R[F2 _{> 2σ(F}2_{)] = 0.039}

wR(F2_{) = 0.108}

S = 1.04 3290 reflections 218 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2_(F

o2) + (0.0409P)2 + 0.3681P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Extinction correction: SHELXL97, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2θ)]-1/4

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 F}2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

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sup-3 Acta Cryst. (2002). E58, o1321–o1322

C19 1.09136 (10) 0.2064 (2) 0.74346 (9) 0.0473 (4) H19A 1.1162 0.2923 0.7889 0.057*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

N1 0.0523 (7) 0.0618 (8) 0.0490 (7) 0.0076 (6) 0.0201 (6) 0.0065 (6) N2 0.0624 (8) 0.0614 (8) 0.0507 (7) 0.0013 (7) 0.0259 (6) −0.0054 (6) N3 0.0502 (7) 0.0686 (9) 0.0506 (7) 0.0119 (6) 0.0190 (6) 0.0032 (6) N4 0.0487 (7) 0.0684 (9) 0.0508 (7) 0.0123 (6) 0.0158 (6) 0.0036 (6) N5 0.0431 (6) 0.0478 (7) 0.0414 (6) 0.0025 (5) 0.0171 (5) 0.0012 (5) C1 0.0581 (9) 0.0663 (10) 0.0489 (9) 0.0060 (8) 0.0183 (7) 0.0091 (8) C2 0.0654 (10) 0.0621 (10) 0.0451 (8) −0.0059 (8) 0.0223 (7) 0.0000 (7) C3 0.0530 (8) 0.0519 (8) 0.0515 (9) 0.0031 (7) 0.0222 (7) −0.0012 (7) C4 0.0451 (7) 0.0413 (7) 0.0473 (8) −0.0017 (6) 0.0198 (6) 0.0002 (6) C5 0.0427 (7) 0.0425 (7) 0.0474 (8) 0.0004 (6) 0.0186 (6) 0.0011 (6) C6 0.0400 (7) 0.0477 (8) 0.0468 (8) −0.0022 (6) 0.0129 (6) 0.0006 (6) C7 0.0382 (7) 0.0429 (7) 0.0419 (7) −0.0013 (6) 0.0133 (6) 0.0011 (6) C8 0.0433 (7) 0.0441 (7) 0.0455 (8) 0.0027 (6) 0.0101 (6) 0.0025 (6) C9 0.0416 (8) 0.0532 (9) 0.0574 (9) 0.0025 (6) 0.0094 (7) 0.0017 (7) C10 0.0509 (9) 0.0549 (9) 0.0543 (9) 0.0043 (7) −0.0029 (7) −0.0037 (7) C11 0.0683 (10) 0.0553 (9) 0.0445 (8) 0.0071 (8) 0.0062 (7) 0.0020 (7) C12 0.0625 (10) 0.0675 (11) 0.0513 (9) −0.0046 (8) 0.0155 (8) 0.0110 (8) C13 0.0475 (8) 0.0656 (10) 0.0479 (8) −0.0080 (7) 0.0056 (6) 0.0081 (7) C14 0.0430 (7) 0.0472 (8) 0.0360 (7) 0.0033 (6) 0.0128 (6) 0.0043 (6) C15 0.0525 (8) 0.0528 (9) 0.0444 (8) −0.0020 (7) 0.0112 (6) −0.0018 (7) C16 0.0828 (12) 0.0524 (9) 0.0437 (8) 0.0007 (8) 0.0219 (8) −0.0062 (7) C17 0.0733 (11) 0.0636 (10) 0.0519 (9) 0.0139 (9) 0.0347 (8) 0.0033 (8) C18 0.0485 (8) 0.0704 (10) 0.0525 (9) 0.0062 (8) 0.0215 (7) 0.0032 (8) C19 0.0453 (8) 0.0566 (9) 0.0410 (7) 0.0025 (7) 0.0129 (6) −0.0022 (7)

Geometric parameters (Å, º)

C6—C7 1.418 (2) C17—C18 1.373 (2) C6—C8 1.481 (2) C17—H17A 0.9300 C7—C14 1.489 (2) C18—C19 1.382 (2) C8—C9 1.386 (2) C18—H18A 0.9300 C8—C13 1.392 (2) C19—H19A 0.9300

C1—N1—C4 115.80 (13) C8—C9—H9A 119.5 C3—N2—C2 115.38 (13) C11—C10—C9 119.83 (14) C5—N3—N4 118.44 (12) C11—C10—H10A 120.1 C6—N4—N3 119.36 (12) C9—C10—H10A 120.1 C7—N5—C5 116.11 (12) C10—C11—C12 120.16 (15) N1—C1—C2 122.40 (15) C10—C11—H11A 119.9 N1—C1—H1B 118.8 C12—C11—H11A 119.9 C2—C1—H1B 118.8 C11—C12—C13 120.17 (15) N2—C2—C1 122.42 (15) C11—C12—H12A 119.9 N2—C2—H2B 118.8 C13—C12—H12A 119.9 C1—C2—H2B 118.8 C12—C13—C8 120.39 (14) N2—C3—C4 122.79 (15) C12—C13—H13A 119.8 N2—C3—H3B 118.6 C8—C13—H13A 119.8 C4—C3—H3B 118.6 C15—C14—C19 119.43 (13) N1—C4—C3 121.14 (14) C15—C14—C7 120.25 (13) N1—C4—C5 117.87 (12) C19—C14—C7 120.31 (13) C3—C4—C5 120.99 (13) C16—C15—C14 119.65 (14) N3—C5—N5 125.46 (13) C16—C15—H15A 120.2 N3—C5—C4 115.91 (12) C14—C15—H15A 120.2 N5—C5—C4 118.59 (12) C17—C16—C15 120.54 (15) N4—C6—C7 119.89 (13) C17—C16—H16A 119.7 N4—C6—C8 116.18 (13) C15—C16—H16A 119.7 C7—C6—C8 123.93 (12) C18—C17—C16 119.77 (14) N5—C7—C6 120.11 (12) C18—C17—H17A 120.1 N5—C7—C14 117.45 (12) C16—C17—H17A 120.1 C6—C7—C14 122.43 (12) C17—C18—C19 120.36 (15) C9—C8—C13 118.53 (14) C17—C18—H18A 119.8 C9—C8—C6 120.42 (13) C19—C18—H18A 119.8 C13—C8—C6 121.04 (13) C18—C19—C14 120.22 (14) C10—C9—C8 120.91 (15) C18—C19—H19A 119.9 C10—C9—H9A 119.5 C14—C19—H19A 119.9

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sup-5 Acta Cryst. (2002). E58, o1321–o1322