N-(Naphthalen-1-yl-methyl-idene)-4H-1,2,4-triazol-4-amine.

In the title mol-ecule, C(13)H(10)N(4), the dihedral angle between the triazole ring and the naphthalene ring system is is 56.1 (2)°. In the crystal, mol-ecules are connected by weak C-H⋯N hydrogen bonds into chains along [100]. A short intra-molecular C-H⋯N contact is also observed.

Related literature

For applications of triazole derivatives, see: Demirbas et al. (2002 ▶); Foroumadi et al. (2003 ▶); He et al. (2006 ▶); Kritsanida et al. (2002 ▶); Manfredini et al. (2000 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H10N4

M = 222.25

Monoclinic,

a = 5.499 (3) Å

b = 10.079 (6) Å

c = 19.942 (12) Å

β = 92.758 (7)°

V = 1104.0 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.2 × 0.15 × 0.1 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.5, T max = 1.0

6574 measured reflections

2168 independent reflections

1787 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.08

2168 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039104/lh5529sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039104/lh5529Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039104/lh5529Isup3.cml

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

C13H10N4	F(000) = 464
Mr = 222.25	Dx = 1.337 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6574 reflections
a = 5.499 (3) Å	θ = 2.0–26°
b = 10.079 (6) Å	µ = 0.09 mm−1
c = 19.942 (12) Å	T = 296 K
β = 92.758 (7)°	Block, colorless
V = 1104.0 (11) Å3	0.2 × 0.15 × 0.1 mm
Z = 4

Bruker APEXII CCD diffractometer	2168 independent reflections
Radiation source: fine-focus sealed tube	1787 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.5, Tmax = 1.0	k = −12→12
6574 measured reflections	l = −24→24

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0598P)2 + 0.1522P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.15 e Å−3
2168 reflections	Δρmin = −0.25 e Å−3
154 parameters

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	0.6439 (2)	0.79790 (12)	0.97839 (6)	0.0429 (3)
N2	0.8048 (2)	0.84041 (11)	1.02686 (6)	0.0384 (3)
N3	0.9117 (2)	0.91095 (15)	1.12480 (6)	0.0570 (4)
N4	1.1212 (2)	0.88352 (14)	1.08514 (6)	0.0517 (3)
C1	0.5720 (2)	0.77204 (14)	0.86143 (6)	0.0382 (3)
C2	0.6174 (3)	0.84224 (16)	0.80284 (7)	0.0494 (4)
H2A	0.7474	0.9012	0.8024	0.059*
C3	0.4736 (3)	0.82456 (17)	0.74739 (8)	0.0595 (5)
H3A	0.5001	0.8713	0.7082	0.071*
C4	0.2871 (3)	0.73591 (17)	0.75027 (7)	0.0544 (4)
H4A	0.1853	0.7253	0.7120	0.065*
C5	0.2370 (3)	0.65767 (13)	0.80837 (7)	0.0400 (3)
C6	0.0469 (3)	0.56297 (15)	0.81066 (8)	0.0489 (4)
H6A	−0.0576	0.5540	0.7729	0.059*
C7	0.0069 (3)	0.48337 (16)	0.86520 (8)	0.0539 (4)
H7A	−0.1223	0.4238	0.8643	0.065*
C8	0.1586 (3)	0.49371 (15)	0.91971 (8)	0.0518 (4)
H8A	0.1405	0.4386	0.9565	0.062*
C9	0.3399 (3)	0.58640 (14)	0.92032 (7)	0.0445 (4)
H9A	0.4410	0.5938	0.9589	0.053*
C10	0.3841 (2)	0.67329 (13)	0.86498 (6)	0.0356 (3)
C11	0.7224 (3)	0.80772 (13)	0.91754 (7)	0.0398 (3)
H11A	0.8792	0.8386	0.9114	0.048*
C12	1.0518 (3)	0.84233 (14)	1.02727 (7)	0.0437 (4)
H12A	1.1494	0.8185	0.9924	0.052*
C13	0.7272 (3)	0.88263 (17)	1.08876 (7)	0.0489 (4)
H13A	0.5666	0.8887	1.1011	0.059*

	U11	U22	U33	U12	U13	U23
N1	0.0343 (6)	0.0541 (7)	0.0390 (6)	−0.0046 (5)	−0.0129 (5)	−0.0057 (5)
N2	0.0317 (6)	0.0439 (6)	0.0385 (6)	−0.0033 (5)	−0.0114 (5)	−0.0025 (5)
N3	0.0428 (8)	0.0794 (10)	0.0471 (7)	−0.0031 (7)	−0.0143 (6)	−0.0101 (7)
N4	0.0383 (7)	0.0617 (8)	0.0534 (7)	−0.0040 (6)	−0.0154 (6)	−0.0039 (6)
C1	0.0372 (7)	0.0403 (7)	0.0362 (7)	0.0026 (6)	−0.0062 (5)	−0.0008 (5)
C2	0.0502 (9)	0.0541 (9)	0.0432 (8)	−0.0083 (7)	−0.0050 (7)	0.0064 (6)
C3	0.0709 (11)	0.0685 (11)	0.0378 (8)	−0.0079 (9)	−0.0108 (7)	0.0141 (7)
C4	0.0592 (10)	0.0630 (10)	0.0389 (8)	0.0006 (8)	−0.0188 (7)	0.0019 (7)
C5	0.0385 (8)	0.0413 (7)	0.0393 (7)	0.0056 (6)	−0.0082 (6)	−0.0065 (6)
C6	0.0434 (8)	0.0501 (9)	0.0516 (8)	0.0021 (7)	−0.0130 (7)	−0.0127 (7)
C7	0.0499 (9)	0.0480 (9)	0.0631 (10)	−0.0109 (7)	−0.0042 (7)	−0.0123 (7)
C8	0.0653 (10)	0.0427 (8)	0.0471 (8)	−0.0082 (7)	−0.0005 (7)	0.0007 (6)
C9	0.0536 (9)	0.0406 (8)	0.0384 (7)	−0.0030 (7)	−0.0088 (6)	−0.0012 (6)
C10	0.0364 (7)	0.0361 (7)	0.0337 (7)	0.0052 (5)	−0.0045 (5)	−0.0046 (5)
C11	0.0350 (7)	0.0406 (7)	0.0429 (8)	−0.0030 (6)	−0.0078 (6)	0.0002 (6)
C12	0.0337 (7)	0.0489 (8)	0.0475 (8)	−0.0005 (6)	−0.0079 (6)	−0.0018 (6)
C13	0.0356 (8)	0.0692 (10)	0.0411 (8)	−0.0031 (7)	−0.0073 (6)	−0.0067 (7)

N1—C11	1.311 (2)	C4—H4A	0.9300
N1—N2	1.3486 (16)	C5—C10	1.3661 (19)
N2—C12	1.3577 (19)	C5—C6	1.418 (2)
N2—C13	1.392 (2)	C6—C7	1.378 (2)
N3—C13	1.2481 (19)	C6—H6A	0.9300
N3—N4	1.455 (2)	C7—C8	1.342 (2)
N4—C12	1.2679 (19)	C7—H7A	0.9300
C1—C2	1.399 (2)	C8—C9	1.366 (2)
C1—C11	1.4059 (19)	C8—H8A	0.9300
C1—C10	1.438 (2)	C9—C10	1.439 (2)
C2—C3	1.340 (2)	C9—H9A	0.9300
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.363 (2)	C12—H12A	0.9300
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.439 (2)
C11—N1—N2	113.90 (12)	C5—C6—H6A	117.9
N1—N2—C12	129.10 (12)	C8—C7—C6	118.53 (15)
N1—N2—C13	120.92 (12)	C8—C7—H7A	120.7
C12—N2—C13	109.85 (11)	C6—C7—H7A	120.7
C13—N3—N4	106.65 (13)	C7—C8—C9	119.02 (15)
C12—N4—N3	110.20 (12)	C7—C8—H8A	120.5
C2—C1—C11	114.43 (13)	C9—C8—H8A	120.5
C2—C1—C10	123.27 (12)	C8—C9—C10	124.04 (13)
C11—C1—C10	122.29 (12)	C8—C9—H9A	118.0
C3—C2—C1	120.01 (15)	C10—C9—H9A	118.0
C3—C2—H2A	120.0	C5—C10—C9	116.64 (13)
C1—C2—H2A	120.0	C5—C10—C1	115.93 (12)
C2—C3—C4	117.87 (15)	C9—C10—C1	127.39 (12)
C2—C3—H3A	121.1	N1—C11—C1	120.65 (13)
C4—C3—H3A	121.1	N1—C11—H11A	119.7
C3—C4—C5	124.52 (13)	C1—C11—H11A	119.7
C3—C4—H4A	117.7	N4—C12—N2	105.52 (13)
C5—C4—H4A	117.7	N4—C12—H12A	127.2
C10—C5—C6	117.34 (13)	N2—C12—H12A	127.2
C10—C5—C4	118.24 (14)	N3—C13—N2	107.76 (14)
C6—C5—C4	124.40 (13)	N3—C13—H13A	126.1
C7—C6—C5	124.29 (13)	N2—C13—H13A	126.1
C7—C6—H6A	117.9

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···N1	0.93	2.36	2.914 (2)	118
C13—H13A···N4i	0.93	2.45	3.330 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯N1	0.93	2.36	2.914 (2)	118
C13—H13A⋯N4i	0.93	2.45	3.330 (3)	157

Symmetry code: (i) .