1 Methyl 3,5 di­phenyl 1H 1,2,4 triazole

Acta Cryst.(2004). E60, o815±o816 DOI: 10.1107/S160053680400861X Serap Yazõcõet al. C₁₅H₁₃N₃

o815

organic papers

Acta Crystallographica Section E Structure Reports

Online

ISSN 1600-5368

1-Methyl-3,5-diphenyl-1

H

-1,2,4-triazole

Serap Yazõcõ,a_{* SËamil IsËõk,}a_Erbil AgÆar,b_{SËenguÈl Alpay KaraogÆlu,}c Olcay Bekircan,d_{Sevgi Kolaylõ,}e Ismet SËenela_{and Orhan}

BuÈyuÈkguÈngoÈra

a_{Department of Physics, Faculty of Arts and}

Sciences, Ondokuz Mayõs University, TR-55139 Kurupelit±Samsun, Turkey,b_{Department of} Chemistry, Ondokuz Mayõs University, TR-55139 Samsun, Turkey,c_{Department of} Biology, Karadeniz Technical University, TR-53100 Rize, Turkey,d_{Department of} Chemistry, Karadeniz Technical University, Giresun, Turkey, ande_{Department of Chemistry,} Karadeniz Technical University, TR-61080 Trabzon, Turkey

Correspondence e-mail: [email protected]

Key indicators Single-crystal X-ray study T= 293 K

Mean(C±C) = 0.005 AÊ Rfactor = 0.051 wRfactor = 0.141

Data-to-parameter ratio = 14.9

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

#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved

Two independent but virtually identical molecules comprise the asymmetric unit in the title compound, C15H13N3, in each of which the triazole ring is planar.

Comment

Triazole ring systems are typically planar six--electron partially aromatic systems. Several articles have been devoted to the synthesis and pharmacological investigation of triazole compounds (e.g.Lùnning et al., 1998); for example, the title compound, (I), displays antibacterial activity against various bacteria (YuÈkseket al., 1997).

Two independent molecules comprise the asymmetric unit in the title compound, (I) (Fig. 1 and Table 1), and these are virtually identical. In each molecule, the non-H atoms are effectively coplanar. The N3a C7a and N1a C8a bonds displays double-bond character, with bond lengths of 1.326 (3) and 1.333 (3) AÊ, respectively; for the second molecule, the values are 1.331 (3) and 1.339 (3) AÊ, respectively. In a closely related compound, 4-(p -methoxyphenyl)-3,5-bis(2-pyridyl)-4H-1,2,4-triazole [(II); Funet al., 1999], the equivalent bond lengths are 1.311 (2) and 1.316 (2) AÊ, respectively. The modest elongations of the bond lengths in (I) can be traced to the presence of the methyl and phenyl groups, which are absent in (II).

The dihedral angles between the triazole and ring C1a±C6a

is 15.5 (7)_{, that between triazole and ring C9a±C14a is} 33.6 (9) _{and that between rings C1a±C6a and C9a±C14a is} 46.1 (8)_{; for moleculebthese are similar at 13.0 (5), 33.5 (1)} and 44.5 (9)_{, respectively.}

Experimental

N-Benzoyl ethylimidobenzoate (0.01 mol) and methylhydrazine (0.01 mol) in ethanol (50 ml) were re¯uxed for 8 h. The resulting solution was evaporated at 313±323 K under reduced pressure and driedin vacuo. The solid residue was recrystallized from ethanol± water (3:1) to give the desired compound in 86% yield (m.p. 361± 362 K).

Crystal data

C15H13N3 Mr= 235.28

Triclinic,P1

a= 7.0796 (12) AÊ

b= 7.0238 (11) AÊ

c= 25.238 (4) AÊ

= 86.954 (14)

= 85.952 (14)

= 82.653 (13)

V= 1240.3 (4) AÊ3

Z= 4

Dx= 1.260 Mg mÿ3

MoKradiation Cell parameters from 7029

re¯ections

= 1.6±22.0

= 0.08 mmÿ1 T= 293 K Prism, colourless 0.320.220.08 mm

Data collection

Stoe IPDS-II diffractometer

!scans

Absorption correction: by integra-tion (X-RED32; Stoe & Cie, 2002)

Tmin= 0.975,Tmax= 0.993

17588 measured re¯ections

4846 independent re¯ections 1571 re¯ections withI> 2(I)

Rint= 0.088 max= 26.0 h=ÿ8!8

k=ÿ7!8

l=ÿ30!30

Re®nement

Re®nement onF2 R[F2_{> 2(F}2_{)] = 0.051} wR(F2_{) = 0.141} S= 0.72 4846 re¯ections 326 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0647P)2]

whereP= (Fo2+ 2Fc2)/3

(/)max= 0.001

max= 0.19 e AÊÿ3

min=ÿ0.19 e AÊÿ3

Extinction correction:SHELXL97 Extinction coef®cient: 0.030 (2)

Table 1

Selected interatomic distances (AÊ).

N2aÐN3a 1.367 (3) N1aÐC7a 1.368 (3) N1aÐC8a 1.333 (3) N2aÐC8a 1.351 (4) N2aÐC15a 1.469 (3) N3aÐC7a 1.326 (3)

N2bÐN3b 1.368 (3) N1bÐC7b 1.360 (4) N1bÐC8b 1.339 (3) N2bÐC8b 1.347 (4) N2bÐC15b 1.465 (3) N3bÐC7b 1.331 (3)

H atoms were included in calculated positions and re®ned using the riding-model approximation, with aromatic CÐH = 0.93 AÊ and methyl CÐH = 0.96 AÊ, and withUiso(H) = 1.5Ueq(parent C atom).

Data collection: X-AREA (Stoe & Cie, 2002); cell re®nement:

X-AREA; data reduction:X-RED32 (Stoe & Cie, 2002); program(s)

used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:ORTEP-3for Windows(Farrugia, 1997); software used to prepare material for publication:WinGX(Farrugia, 1999).

References

Farrugia, L. J. (1997).J. Appl. Cryst.30, 565. Farrugia, L. J. (1999).J. Appl. Cryst.32, 837±838.

Fun, H.-K., Chinnakali, K., Shao, S., Zhu, D. & You, X.-Z. (1999).Acta Cryst.

C55, 770±772.

Lùnning, P. E., Geisler, J. & Dowsett, M. (1998).Breast Can. Res. Treat.49

(Suppl. 1), S53±S57.

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

Stoe & Cie (2002).X-AREAandX-RED32. Stoe & Cie, Darmstadt, Germany. YuÈksek, H., DemirbasË, A., IÇkizler, A., Johanson C. B., CËelik, C. & IÇkizler A.

(1997).Arzneim.Forsch.(Drug Res.),47, 405±409.

Figure 1

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sup-1 Acta Cryst. (2004). E60, o815–o816

supporting information

Acta Cryst. (2004). E60, o815–o816 [https://doi.org/10.1107/S160053680400861X]

1-Methyl-3,5-diphenyl-1

H

-1,2,4-triazole

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3,5-Diphenyl-1-methyl-1H-1,2,4-triazole

Crystal data

C15H13N3

Mr = 235.28

Triclinic, P1 Hall symbol: -P 1

a = 7.0796 (12) Å

b = 7.0238 (11) Å

c = 25.238 (4) Å

α = 86.954 (14)°

β = 85.952 (14)°

γ = 82.653 (13)°

V = 1240.3 (4) Å3

Z = 4

F(000) = 496

Dx = 1.260 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 7029 reflections

θ = 1.6–22.0°

µ = 0.08 mm−1

T = 293 K

Prismatic, colourless 0.32 × 0.22 × 0.08 mm

Data collection

Stoe IPDS-2 diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

Detector resolution: 6.67 pixels mm-1

ω rotation scans

Absorption correction: integration numerical

Tmin = 0.975, Tmax = 0.993

17588 measured reflections 4846 independent reflections 1571 reflections with I > 2σ(I)

Rint = 0.088

θmax = 26.0°, θmin = 1.6°

h = −8→8

k = −7→8

l = −30→30

Refinement

Refinement on F2 Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.051}

wR(F2_{) = 0.141}

S = 0.72 4846 reflections 326 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 atoms treated by a mixture of independent and constrained refinement

w = 1/[σ2_(F

o2) + (0.0647P)2] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.001

Δρmax = 0.19 e Å−3 Δρmin = −0.19 e Å−3

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₎

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sup-3 Acta Cryst. (2004). E60, o815–o816

H3B 0.8856 −0.1439 0.3511 0.112* C4B 0.8157 (5) 0.0962 (7) 0.30668 (17) 0.0968 (12) H4B 0.8280 0.0381 0.2742 0.116* C5B 0.7625 (5) 0.2904 (7) 0.30881 (15) 0.0928 (11) H5B 0.7388 0.3637 0.2777 0.111* C6B 0.7439 (4) 0.3780 (5) 0.35700 (14) 0.0786 (9) H6B 0.7064 0.5095 0.3583 0.094* C7B 0.7650 (4) 0.3623 (5) 0.45508 (13) 0.0648 (8) C15B 0.7037 (4) 0.7689 (4) 0.53087 (13) 0.0771 (9) H15D 0.7068 0.8604 0.5013 0.116* H15E 0.8019 0.7856 0.5540 0.116* H15F 0.5815 0.7885 0.5501 0.116* C8B 0.7428 (4) 0.4016 (4) 0.53780 (13) 0.0640 (8) C9B 0.7286 (4) 0.3659 (4) 0.59516 (13) 0.0658 (8) C14B 0.8021 (4) 0.4793 (5) 0.63015 (14) 0.0760 (9) H14B 0.8620 0.5841 0.6170 0.091* C13B 0.7871 (5) 0.4378 (6) 0.68429 (14) 0.0840 (10) H13B 0.8369 0.5152 0.7072 0.101* C12B 0.7008 (5) 0.2858 (6) 0.70448 (15) 0.0883 (11) H12B 0.6910 0.2594 0.7410 0.106* C11B 0.6270 (5) 0.1696 (5) 0.67022 (16) 0.0899 (11) H11B 0.5686 0.0643 0.6837 0.108* C10B 0.6409 (4) 0.2112 (5) 0.61637 (14) 0.0770 (9) H10B 0.5903 0.1337 0.5937 0.092* N2B 0.7356 (3) 0.5738 (3) 0.51138 (11) 0.0665 (7) N1B 0.7618 (3) 0.2627 (3) 0.50276 (11) 0.0672 (7) N3B 0.7490 (3) 0.5526 (4) 0.45762 (10) 0.0699 (7)

Atomic displacement parameters (Å2₎

N3A 0.0667 (18) 0.0674 (17) 0.076 (2) −0.0116 (14) −0.0037 (14) −0.0007 (14) C1B 0.0560 (18) 0.069 (2) 0.069 (2) −0.0115 (16) −0.0025 (15) −0.0035 (18) C2B 0.081 (2) 0.077 (2) 0.077 (2) −0.0085 (19) 0.0007 (18) −0.0069 (19) C3B 0.096 (3) 0.083 (3) 0.101 (3) −0.010 (2) 0.006 (2) −0.020 (3) C4B 0.092 (3) 0.117 (4) 0.085 (3) −0.026 (3) 0.000 (2) −0.019 (3) C5B 0.095 (3) 0.112 (3) 0.076 (3) −0.025 (2) −0.013 (2) −0.005 (2) C6B 0.075 (2) 0.080 (2) 0.084 (3) −0.0127 (18) −0.0136 (18) −0.005 (2) C7B 0.0601 (19) 0.062 (2) 0.073 (2) −0.0091 (16) −0.0051 (15) 0.0010 (18) C15B 0.085 (2) 0.056 (2) 0.091 (3) −0.0087 (17) −0.0053 (18) −0.0078 (17) C8B 0.0585 (19) 0.059 (2) 0.075 (2) −0.0056 (16) −0.0057 (16) −0.0038 (19) C9B 0.0558 (18) 0.066 (2) 0.076 (2) −0.0096 (16) −0.0024 (16) −0.0034 (18) C14B 0.067 (2) 0.077 (2) 0.087 (3) −0.0176 (18) −0.0042 (18) −0.005 (2) C13B 0.088 (3) 0.091 (3) 0.073 (3) −0.009 (2) −0.0106 (19) −0.006 (2) C12B 0.077 (2) 0.116 (3) 0.071 (2) −0.015 (2) −0.0024 (19) 0.005 (2) C11B 0.091 (3) 0.092 (3) 0.087 (3) −0.019 (2) −0.008 (2) 0.016 (2) C10B 0.080 (2) 0.072 (2) 0.080 (3) −0.0165 (19) −0.0044 (18) 0.0004 (19) N2B 0.0661 (16) 0.0576 (17) 0.0758 (19) −0.0071 (13) −0.0038 (13) −0.0054 (15) N1B 0.0661 (16) 0.0637 (17) 0.0722 (19) −0.0105 (14) −0.0033 (13) −0.0034 (15) N3B 0.0720 (17) 0.0687 (19) 0.0689 (19) −0.0106 (14) −0.0041 (13) 0.0012 (14)

Geometric parameters (Å, º)

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sup-5 Acta Cryst. (2004). E60, o815–o816

C15A—H15C 0.9600 C13B—C12B 1.356 (5) C8A—C9A 1.458 (4) C13B—H13B 0.9300 C9A—C10A 1.375 (4) C12B—C11B 1.391 (5) C9A—C14A 1.394 (4) C12B—H12B 0.9300 C14A—C13A 1.397 (5) C11B—C10B 1.374 (4) C14A—H14A 0.9300 C11B—H11B 0.9300 C13A—C12A 1.365 (5) C10B—H10B 0.9300

C13A—C12A—H12A 120.4 C13B—C12B—H12B 120.2 C11A—C12A—H12A 120.4 C11B—C12B—H12B 120.2 C12A—C11A—C10A 120.5 (4) C10B—C11B—C12B 119.6 (4) C12A—C11A—H11A 119.7 C10B—C11B—H11B 120.2 C10A—C11A—H11A 119.7 C12B—C11B—H11B 120.2 C11A—C10A—C9A 121.3 (3) C11B—C10B—C9B 121.5 (3) C11A—C10A—H10A 119.3 C11B—C10B—H10B 119.3 C9A—C10A—H10A 119.3 C9B—C10B—H10B 119.3 C8A—N2A—N3A 110.6 (2) C8B—N2B—N3B 110.8 (2) C8A—N2A—C15A 130.8 (3) C8B—N2B—C15B 130.8 (3) N3A—N2A—C15A 118.5 (3) N3B—N2B—C15B 118.3 (3) C8A—N1A—C7A 103.4 (2) C8B—N1B—C7B 103.0 (2) C7A—N3A—N2A 102.1 (2) C7B—N3B—N2B 101.5 (2)

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sup-7 Acta Cryst. (2004). E60, o815–o816