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

In the title compound, C(19)H(15)N(3), 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 ▶).

Experimental

Crystal data

C19H15N3

M = 285.34

Monoclinic,

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.

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

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

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

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

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

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%

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

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.

	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*

	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)

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)