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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jun 30;67(Pt 7):o1856. doi: 10.1107/S1600536811019994

1-Benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole

Juan I Sarmiento-Sánchez a, Gerardo Aguirre a, Ignacio A Rivero a,*
PMCID: PMC3151948  PMID: 21837221

Abstract

In the title compound, C19H15N3, the benzyl group is almost perpendicular to the triazole ring [dihedral angle = 80.64 (8)°], while the napthyl group makes an angle of 30.27 (12)° with the plane of the triazole ring. This conformation is different from the 1-benzyl-4-phenyl-1H-1,2,3-triazole analogue, which has the benzyl ring system at an angle of 87.94° and the phenyl group at an angle of 3.35° to the plane of the triazole ring.

Related literature

For the biological activity of triazoles, see: Alvarez et al. (1994 ▶ ); Brockunier et al. (2000 ▶); Genin et al. (2000 ▶); Katritsky et al. (1996 ▶ ). For related structures, see: Bi (2010 ▶); Huang et al. (2010 ▶); Jabli et al. (2010 ▶); Key et al. (2008 ▶); Makam & Yulin (2004 ▶); Santos-Contreras et al. (2009 ▶): Vaqueiro (2006 ▶).graphic file with name e-67-o1856-scheme1.jpg

Experimental

Crystal data

  • C19H15N3

  • M r = 285.34

  • Monoclinic, Inline graphic

  • a = 9.896 (2) Å

  • b = 11.038 (3) Å

  • c = 14.136 (4) Å

  • β = 102.701 (13)°

  • V = 1506.2 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.5 × 0.48 × 0.28 mm

Data collection

  • Siemens P4 diffractometer

  • 3663 measured reflections

  • 3471 independent reflections

  • 1730 reflections with I > 2σ(I)

  • R int = 0.028

  • 3 standard reflections every 97 reflections intensity decay: 5.4%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069

  • wR(F 2) = 0.202

  • S = 1.01

  • 3471 reflections

  • 199 parameters

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.17 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811019994/fl2334sup1.cif

e-67-o1856-sup1.cif (18KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019994/fl2334Isup2.hkl

e-67-o1856-Isup2.hkl (170.2KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811019994/fl2334Isup3.cml

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

Acknowledgments

We gratefully acknowledge support of this project by the Consejo Nacional de Ciencia y Tecnología (CONACyT, grant No. SEP-2004-CO1–47835) and the Dirección General de Educación Superior Tecnológica (DGEST). JS thanks CONACYT for a graduate scholarship.

supplementary crystallographic information

Comment

In recent years, triazole compounds have received much attention due to their wide range of applications in organic and medicinal chemistry. Specifically, 1,2,3-triazoles have been used in pharmaceuticals, agrochemicals, dyes, photographic materials and corrosion inhibitors (Katritsky et al., 1996). There are numerous examples in the literature of the biological activity of triazole compounds acting as as anti-HIV agents (Alvarez et al., 1994) or as antibiotics due to their antimicrobial activity against Gram positive bacteria (Genin et al., 2000) and as selective β3 adrenergic agonist receptors (Brockunier et al., 2000).

The molecular structure of (I) is shown in Fig. 1. The molecule shows that the phenyl group and the triazole heterocycle are linked by the methylene group. The carbon atom C13 with a C14—C13—N1 angle of 112.5 (2)o is distorted from ideal tetrahedral geometry (109.7¯). This can be attributed to steric factors of adjacent cyclic systems. Also, the bonds distances N3—C11, C11—C12, C12—N1, N1—N2 and N2—N3 are 1.353 (3), 1.353 (4), 1.335 (3), 1.337 (3) and 1.321 (3) Å, respectively, which agree with the C═C, N═N and C—N distances found in the literature for compounds having triazole heterocycles (Huang et al., 2010; Jabli et al., 2010; Key et al. 2008). In addition, C12—N1 and C11—N3 are significantly shorter that the C—N single bonds (1.47 Å) (Vaqueiro, 2006; Bi, 2010) but longer than true C—N double bonds (1.28 Å) (Santos-Contreras et al., 2009). This indicates a delocalization of electrons in the triazolyl system.

As shown in Fig. 1, the molecule shows the benzyl group is located above the plane of the triazole at a dihedral angle of 80.64 (0.08)° and the naphthyl group is at an angle fo 30.27 (0.12)°. This conformation is different from its analogue 1-benzyl-4-phenyl-1H-1, 2,3-triazole which presents the benzyl at an dihedral angle of 87.94° and the phenyl at an angle of 3.35° to the plane of the triazole (Makam & Yulin, 2004).

Experimental

Experimental

All reagents were purchased in the highest quality available and were used without further purification. The solvents used in column chromatography were obtained from commercial suppliers and used without distillation. To a solution tert-BuOH/H2O (6 ml 1:1 v/v) was added benzyl bromide (1.684 mmol), sodium azide (1.684 mmol), 1-ethynyl-naphthalene (1.684 mmol), copper(II) sulfate (0.084 mmol, 5% mol) and sodium ascorbate (0.168 mmol, 10% mol) with vigorous stirring at 60 °C for 8 h. The reaction mixture was filtered with diatomaceous earth (kieselguhr) or zeolite and silica gel in vacuo, then extracted with ethyl acetate (60 ml). The extracts were combined and dried over anhydrous sodium sulfate. After evaporation of the solvent, the residual oil solidified and was purified by flash chromatography to give (I) (petroleum ether/EtOAc 1:1 v/v). Yield 85%; pale yellow solid; mp 89–90 °C; 1H-NMR (CDCl3, 200 MHz): δ 8.39–8.34 (m, 1H), 7.88–7.82 (m, 2H), 7.71 (s, 1H), 7.69–7.66 (d, J = 7.33 Hz, 1H), 7.52–7.47 (dd, J = 6.42, 3.48 Hz, 4H), 7.37–7.36 (d, J = 1.83 Hz, 4H), 5.61 (s, 2H); 13C-NMR (CDCl3, 50 MHz): δ 147.3, 134.6, 133.8, 131.0, 129.1, 128.8, 128.7, 128.3, 128.0, 127.1, 126.5, 125.9, 125.4, 125.2, 122.4, 54.1; IR (KBr, pellet): 1686, 1601, 1454 cm-1; ESI-MS m/z: 286 [M+H]+, 308 [M+Na]+, 324 [M+K]+, 593 [2M+Na]+.

Crystallization

50 mg of (I) compound was placed for diffusion in a glass vial with chloroform-petroleum ether for one day. The crystals, suitable for data collection, were separated by filtration.

Refinement

Refinement for H atoms was carried out using a riding model, with distances constrained to: 0.93 Å for aromatic CH, 0.98 Å for methine CH. Isotropic U parameters were fixed to Uiso(H)=1.2Ueq(carrier atom) for aromatic CH.

Figures

Fig. 1.

Fig. 1.

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The title compound (I) with displacement ellipsoids drawn at 30% probability level.

Crystal data

C19H15N3 F(000) = 600
Mr = 285.34 Dx = 1.258 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 36 reflections
a = 9.896 (2) Å θ = 4.6–12.4°
b = 11.038 (3) Å µ = 0.08 mm−1
c = 14.136 (4) Å T = 298 K
β = 102.701 (13)° Prismatic, colorless
V = 1506.2 (6) Å3 0.5 × 0.48 × 0.28 mm
Z = 4
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Data collection

Siemens P4 diffractometer Rint = 0.028
Radiation source: fine-focus sealed tube θmax = 27.5°, θmin = 2.1°
graphite h = 0→12
2θ/ω scans k = 0→14
3663 measured reflections l = −18→17
3471 independent reflections 3 standard reflections every 97 reflections
1730 reflections with I > 2σ(I) intensity decay: 5.4%
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202 H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0839P)2 + 0.308P] where P = (Fo2 + 2Fc2)/3
3471 reflections (Δ/σ)max < 0.001
199 parameters Δρmax = 0.40 e Å−3
0 restraints Δρmin = −0.17 e Å−3
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
N1 0.2899 (2) 0.3968 (2) 0.18018 (16) 0.0603 (7)
N2 0.3058 (3) 0.2778 (3) 0.19682 (18) 0.0688 (7)
N3 0.4044 (3) 0.2660 (2) 0.27619 (18) 0.0665 (7)
C1 0.5662 (3) 0.4031 (3) 0.39312 (19) 0.0548 (7)
C2 0.6434 (3) 0.5043 (3) 0.3915 (2) 0.0688 (9)
H2B 0.6208 0.5550 0.3377 0.083*
C3 0.7552 (4) 0.5365 (3) 0.4664 (2) 0.0779 (10)
H3B 0.8053 0.6066 0.4613 0.093*
C4 0.7905 (4) 0.4661 (3) 0.5459 (2) 0.0773 (10)
H4A 0.8655 0.4870 0.5954 0.093*
C5 0.7114 (3) 0.3581 (3) 0.55387 (19) 0.0592 (8)
C6 0.7469 (4) 0.2850 (3) 0.6363 (2) 0.0756 (10)
H6A 0.8207 0.3068 0.6864 0.091*
C7 0.6745 (4) 0.1828 (3) 0.6434 (2) 0.0779 (10)
H7A 0.6995 0.1339 0.6981 0.093*
C8 0.5616 (3) 0.1501 (3) 0.5686 (2) 0.0726 (9)
H8A 0.5123 0.0799 0.5748 0.087*
C9 0.5231 (3) 0.2188 (3) 0.4877 (2) 0.0657 (8)
H9A 0.4475 0.1958 0.4394 0.079*
C10 0.5991 (3) 0.3282 (2) 0.47587 (18) 0.0519 (7)
C11 0.4501 (3) 0.3772 (3) 0.30902 (19) 0.0530 (7)
C12 0.3770 (3) 0.4599 (3) 0.2479 (2) 0.0627 (8)
H12A 0.3856 0.5438 0.2521 0.075*
C13 0.1908 (3) 0.4396 (4) 0.0935 (2) 0.0837 (11)
H13A 0.1334 0.3723 0.0644 0.100*
H13B 0.2413 0.4688 0.0465 0.100*
C14 0.0994 (3) 0.5392 (3) 0.11590 (18) 0.0559 (7)
C15 0.1201 (3) 0.6574 (3) 0.0925 (2) 0.0713 (9)
H15A 0.1931 0.6762 0.0634 0.086*
C16 0.0351 (4) 0.7485 (3) 0.1112 (2) 0.0768 (10)
H16A 0.0509 0.8280 0.0946 0.092*
C17 −0.0723 (3) 0.7230 (3) 0.1539 (2) 0.0687 (9)
H17A −0.1301 0.7846 0.1664 0.082*
C18 −0.0945 (3) 0.6056 (3) 0.1783 (2) 0.0680 (9)
H18A −0.1673 0.5875 0.2078 0.082*
C19 −0.0089 (3) 0.5140 (3) 0.1592 (2) 0.0617 (8)
H19A −0.0247 0.4345 0.1759 0.074*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
N1 0.0498 (14) 0.0771 (18) 0.0486 (13) 0.0138 (13) −0.0007 (11) −0.0144 (12)
N2 0.0644 (16) 0.0719 (19) 0.0660 (16) −0.0103 (14) 0.0052 (13) −0.0132 (14)
N3 0.0671 (16) 0.0661 (17) 0.0624 (15) −0.0031 (13) 0.0060 (13) 0.0003 (13)
C1 0.0597 (17) 0.0507 (17) 0.0522 (16) 0.0095 (14) 0.0082 (13) −0.0086 (13)
C2 0.078 (2) 0.0553 (19) 0.0652 (19) −0.0055 (17) −0.0020 (16) −0.0066 (15)
C3 0.093 (2) 0.0549 (19) 0.075 (2) −0.0171 (17) −0.0047 (19) −0.0025 (17)
C4 0.083 (2) 0.069 (2) 0.068 (2) −0.0057 (18) −0.0085 (18) −0.0155 (18)
C5 0.0637 (18) 0.0638 (19) 0.0460 (15) 0.0207 (15) 0.0033 (14) −0.0046 (13)
C6 0.078 (2) 0.086 (3) 0.0567 (18) 0.023 (2) 0.0022 (17) −0.0063 (17)
C7 0.084 (2) 0.083 (3) 0.067 (2) 0.021 (2) 0.0194 (19) 0.0096 (18)
C8 0.076 (2) 0.076 (2) 0.071 (2) 0.0046 (18) 0.0274 (18) 0.0163 (17)
C9 0.0626 (19) 0.069 (2) 0.0681 (19) 0.0069 (16) 0.0205 (15) 0.0056 (16)
C10 0.0551 (16) 0.0530 (16) 0.0463 (14) 0.0164 (14) 0.0085 (13) −0.0066 (12)
C11 0.0507 (15) 0.0598 (18) 0.0459 (14) 0.0107 (13) 0.0049 (12) −0.0105 (13)
C12 0.0637 (18) 0.0594 (18) 0.0568 (16) 0.0166 (15) −0.0043 (14) −0.0165 (14)
C13 0.068 (2) 0.126 (3) 0.0482 (17) 0.034 (2) −0.0059 (15) −0.0121 (18)
C14 0.0457 (15) 0.076 (2) 0.0414 (14) 0.0091 (14) −0.0001 (12) 0.0008 (14)
C15 0.0512 (18) 0.098 (3) 0.0633 (19) −0.0065 (18) 0.0092 (15) 0.0198 (18)
C16 0.080 (2) 0.067 (2) 0.074 (2) −0.0104 (19) −0.0025 (19) 0.0197 (17)
C17 0.068 (2) 0.063 (2) 0.0697 (19) 0.0095 (16) 0.0046 (17) 0.0042 (16)
C18 0.0528 (18) 0.081 (2) 0.075 (2) −0.0010 (17) 0.0227 (16) 0.0033 (17)
C19 0.0641 (18) 0.0548 (18) 0.0645 (18) −0.0021 (15) 0.0109 (15) 0.0042 (14)
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Geometric parameters (Å, °)

N1—C12 1.335 (3) C8—C9 1.356 (4)
N1—N2 1.337 (3) C8—H8A 0.9300
N1—C13 1.470 (3) C9—C10 1.452 (4)
N2—N3 1.321 (3) C9—H9A 0.9300
N3—C11 1.353 (3) C11—C12 1.353 (4)
C1—C2 1.357 (4) C12—H12A 0.9300
C1—C10 1.410 (4) C13—C14 1.500 (4)
C1—C11 1.488 (4) C13—H13A 0.9700
C2—C3 1.399 (4) C13—H13B 0.9700
C2—H2B 0.9300 C14—C15 1.372 (4)
C3—C4 1.348 (4) C14—C19 1.375 (4)
C3—H3B 0.9300 C15—C16 1.374 (5)
C4—C5 1.444 (5) C15—H15A 0.9300
C4—H4A 0.9300 C16—C17 1.363 (5)
C5—C6 1.397 (4) C16—H16A 0.9300
C5—C10 1.421 (4) C17—C18 1.371 (4)
C6—C7 1.352 (5) C17—H17A 0.9300
C6—H6A 0.9300 C18—C19 1.384 (4)
C7—C8 1.407 (5) C18—H18A 0.9300
C7—H7A 0.9300 C19—H19A 0.9300
C12—N1—N2 110.8 (2) C1—C10—C9 123.5 (3)
C12—N1—C13 129.6 (3) C5—C10—C9 116.1 (3)
N2—N1—C13 119.6 (3) C12—C11—N3 107.6 (2)
N3—N2—N1 106.4 (2) C12—C11—C1 126.2 (3)
N2—N3—C11 109.3 (2) N3—C11—C1 126.1 (3)
C2—C1—C10 117.9 (3) N1—C12—C11 106.0 (3)
C2—C1—C11 118.9 (3) N1—C12—H12A 127.0
C10—C1—C11 123.2 (3) C11—C12—H12A 127.0
C1—C2—C3 123.4 (3) N1—C13—C14 112.5 (2)
C1—C2—H2B 118.3 N1—C13—H13A 109.1
C3—C2—H2B 118.3 C14—C13—H13A 109.1
C4—C3—C2 120.1 (3) N1—C13—H13B 109.1
C4—C3—H3B 120.0 C14—C13—H13B 109.1
C2—C3—H3B 120.0 H13A—C13—H13B 107.8
C3—C4—C5 119.7 (3) C15—C14—C19 118.1 (3)
C3—C4—H4A 120.1 C15—C14—C13 121.1 (3)
C5—C4—H4A 120.1 C19—C14—C13 120.7 (3)
C6—C5—C10 121.6 (3) C14—C15—C16 121.4 (3)
C6—C5—C4 120.0 (3) C14—C15—H15A 119.3
C10—C5—C4 118.4 (3) C16—C15—H15A 119.3
C7—C6—C5 120.3 (3) C17—C16—C15 120.2 (3)
C7—C6—H6A 119.9 C17—C16—H16A 119.9
C5—C6—H6A 119.9 C15—C16—H16A 119.9
C6—C7—C8 120.3 (3) C16—C17—C18 119.4 (3)
C6—C7—H7A 119.9 C16—C17—H17A 120.3
C8—C7—H7A 119.9 C18—C17—H17A 120.3
C9—C8—C7 121.4 (3) C17—C18—C19 120.2 (3)
C9—C8—H8A 119.3 C17—C18—H18A 119.9
C7—C8—H8A 119.3 C19—C18—H18A 119.9
C8—C9—C10 120.4 (3) C14—C19—C18 120.7 (3)
C8—C9—H9A 119.8 C14—C19—H19A 119.7
C10—C9—H9A 119.8 C18—C19—H19A 119.7
C1—C10—C5 120.4 (3)
C12—N1—N2—N3 0.0 (3) C8—C9—C10—C5 −1.2 (4)
C13—N1—N2—N3 177.3 (2) N2—N3—C11—C12 0.1 (3)
N1—N2—N3—C11 −0.1 (3) N2—N3—C11—C1 −176.1 (2)
C10—C1—C2—C3 1.4 (5) C2—C1—C11—C12 −27.0 (4)
C11—C1—C2—C3 −179.5 (3) C10—C1—C11—C12 151.9 (3)
C1—C2—C3—C4 −0.6 (5) C2—C1—C11—N3 148.4 (3)
C2—C3—C4—C5 −0.7 (5) C10—C1—C11—N3 −32.6 (4)
C3—C4—C5—C6 −179.7 (3) N2—N1—C12—C11 0.1 (3)
C3—C4—C5—C10 1.1 (5) C13—N1—C12—C11 −176.9 (3)
C10—C5—C6—C7 0.2 (5) N3—C11—C12—N1 −0.1 (3)
C4—C5—C6—C7 −179.0 (3) C1—C11—C12—N1 176.0 (2)
C5—C6—C7—C8 −0.9 (5) C12—N1—C13—C14 −50.4 (4)
C6—C7—C8—C9 0.5 (5) N2—N1—C13—C14 132.8 (3)
C7—C8—C9—C10 0.6 (5) N1—C13—C14—C15 104.8 (3)
C2—C1—C10—C5 −1.0 (4) N1—C13—C14—C19 −76.2 (4)
C11—C1—C10—C5 −179.9 (2) C19—C14—C15—C16 −0.3 (4)
C2—C1—C10—C9 178.7 (3) C13—C14—C15—C16 178.7 (3)
C11—C1—C10—C9 −0.2 (4) C14—C15—C16—C17 0.1 (5)
C6—C5—C10—C1 −179.5 (3) C15—C16—C17—C18 0.2 (5)
C4—C5—C10—C1 −0.3 (4) C16—C17—C18—C19 −0.3 (5)
C6—C5—C10—C9 0.8 (4) C15—C14—C19—C18 0.2 (4)
C4—C5—C10—C9 −180.0 (3) C13—C14—C19—C18 −178.8 (3)
C8—C9—C10—C1 179.1 (3) C17—C18—C19—C14 0.1 (5)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2334).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811019994/fl2334sup1.cif

e-67-o1856-sup1.cif (18KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019994/fl2334Isup2.hkl

e-67-o1856-Isup2.hkl (170.2KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811019994/fl2334Isup3.cml

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

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

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