N-[4-(Dimethyl-amino)-benzyl-idene]-4H-1,2,4-triazol-4-amine.

The title compound, C(11)H(13)N(5), is a Schiff base synthesized by the reaction of 4-amino-4H-1,2,4-triazole and 4-(dimethyl-amino)-benzaldehyde. The dihedral angle between the benzene and triazole rings is 43.09 (11)°. The crystal structure displays weak C-H⋯N inter-actions.

Related literature

For the biological activity of triazole derivatives, see: Modzelewska & Kalabun (1999 ▶); Rollas et al. (1993 ▶); Todoulou et al. (1994 ▶); Demirbas et al. (2002 ▶); Kahveci et al. (2003 ▶). For 4-amino-1,2,4-triazole Schiff bases, see: Desenko & Khim (1995 ▶); Kargin et al. (1988 ▶).

Experimental

Crystal data

C11H13N5

M = 215.26

Monoclinic,

a = 10.3665 (16) Å

b = 11.1585 (19) Å

c = 9.5248 (12) Å

β = 90.257 (1)°

V = 1101.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.52 × 0.15 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.957, T max = 0.991

5465 measured reflections

1940 independent reflections

1184 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.119

S = 1.00

1940 reflections

148 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014511/ff2062sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014511/ff2062Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014511/ff2062Isup3.cml

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

C11H13N5	F(000) = 456
Mr = 215.26	Dx = 1.298 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1214 reflections
a = 10.3665 (16) Å	θ = 2.7–23.0°
b = 11.1585 (19) Å	µ = 0.08 mm−1
c = 9.5248 (12) Å	T = 298 K
β = 90.257 (1)°	Cuboid, colourless
V = 1101.8 (3) Å3	0.52 × 0.15 × 0.11 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1940 independent reflections
Radiation source: fine-focus sealed tube	1184 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
phi and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
Tmin = 0.957, Tmax = 0.991	k = −13→9
5465 measured reflections	l = −11→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0462P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1940 reflections	Δρmax = 0.17 e Å−3
148 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.086 (5)

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	0.20167 (17)	0.23656 (19)	0.4358 (2)	0.0665 (6)
N2	0.24339 (17)	0.13578 (17)	0.36475 (19)	0.0599 (5)
N3	0.34969 (14)	0.14765 (14)	0.56204 (17)	0.0461 (4)
N4	0.43764 (14)	0.11434 (15)	0.66817 (17)	0.0498 (5)
N5	0.87803 (15)	0.16192 (15)	1.14369 (18)	0.0590 (5)
C1	0.33047 (19)	0.08539 (19)	0.4428 (2)	0.0540 (6)
H1	0.3740	0.0154	0.4195	0.065*
C2	0.26690 (19)	0.2406 (2)	0.5530 (2)	0.0588 (6)
H2	0.2576	0.2996	0.6212	0.071*
C3	0.49452 (17)	0.20274 (18)	0.7270 (2)	0.0469 (5)
H3	0.4751	0.2797	0.6959	0.056*
C4	0.58726 (17)	0.18934 (17)	0.8392 (2)	0.0437 (5)
C5	0.61841 (19)	0.07978 (19)	0.8997 (2)	0.0539 (6)
H5	0.5744	0.0114	0.8707	0.065*
C6	0.7122 (2)	0.06956 (19)	1.0008 (2)	0.0581 (6)
H6	0.7301	−0.0051	1.0396	0.070*
C7	0.78200 (17)	0.17091 (18)	1.0468 (2)	0.0458 (5)
C8	0.74731 (17)	0.28123 (18)	0.9884 (2)	0.0491 (6)
H8	0.7890	0.3504	1.0186	0.059*
C9	0.65320 (18)	0.28964 (18)	0.8876 (2)	0.0477 (6)
H9	0.6329	0.3644	0.8505	0.057*
C10	0.9193 (3)	0.0473 (2)	1.1988 (3)	0.0853 (9)
H10A	0.8525	0.0144	1.2566	0.128*
H10B	0.9963	0.0579	1.2539	0.128*
H10C	0.9366	−0.0064	1.1224	0.128*
C11	0.9429 (2)	0.2687 (2)	1.1945 (2)	0.0691 (7)
H11A	0.9861	0.3074	1.1180	0.104*
H11B	1.0049	0.2468	1.2652	0.104*
H11C	0.8806	0.3225	1.2340	0.104*

	U11	U22	U33	U12	U13	U23
N1	0.0658 (12)	0.0829 (14)	0.0507 (13)	0.0148 (10)	−0.0210 (10)	−0.0039 (11)
N2	0.0641 (11)	0.0706 (13)	0.0448 (12)	−0.0003 (10)	−0.0169 (9)	0.0003 (10)
N3	0.0464 (9)	0.0559 (11)	0.0359 (10)	−0.0001 (8)	−0.0119 (8)	0.0019 (9)
N4	0.0521 (10)	0.0569 (11)	0.0403 (11)	0.0002 (8)	−0.0165 (8)	0.0024 (9)
N5	0.0578 (10)	0.0678 (13)	0.0512 (12)	0.0076 (10)	−0.0251 (9)	−0.0019 (10)
C1	0.0651 (13)	0.0536 (13)	0.0432 (14)	−0.0038 (11)	−0.0132 (11)	−0.0005 (11)
C2	0.0547 (13)	0.0712 (16)	0.0503 (15)	0.0103 (12)	−0.0140 (11)	−0.0079 (12)
C3	0.0441 (11)	0.0530 (13)	0.0436 (14)	0.0054 (10)	−0.0059 (10)	−0.0006 (11)
C4	0.0454 (11)	0.0481 (12)	0.0374 (13)	0.0048 (9)	−0.0075 (9)	−0.0018 (10)
C5	0.0642 (13)	0.0516 (13)	0.0456 (14)	−0.0066 (10)	−0.0164 (11)	−0.0038 (11)
C6	0.0744 (14)	0.0508 (13)	0.0488 (14)	0.0075 (11)	−0.0204 (12)	0.0025 (11)
C7	0.0472 (11)	0.0536 (13)	0.0364 (13)	0.0077 (10)	−0.0068 (9)	−0.0039 (10)
C8	0.0462 (11)	0.0535 (13)	0.0475 (14)	−0.0016 (10)	−0.0104 (10)	−0.0063 (11)
C9	0.0489 (11)	0.0493 (13)	0.0448 (14)	0.0051 (9)	−0.0099 (10)	−0.0002 (10)
C10	0.0898 (17)	0.089 (2)	0.0766 (19)	0.0287 (15)	−0.0392 (15)	0.0001 (16)
C11	0.0548 (13)	0.0922 (18)	0.0602 (17)	−0.0066 (12)	−0.0212 (12)	−0.0041 (14)

N1—C2	1.303 (3)	C4—C9	1.389 (3)
N1—N2	1.383 (2)	C5—C6	1.370 (3)
N2—C1	1.295 (2)	C5—H5	0.9300
N3—C1	1.346 (2)	C6—C7	1.411 (3)
N3—C2	1.349 (2)	C6—H6	0.9300
N3—N4	1.408 (2)	C7—C8	1.397 (3)
N4—C3	1.277 (2)	C8—C9	1.369 (3)
N5—C7	1.358 (2)	C8—H8	0.9300
N5—C10	1.446 (3)	C9—H9	0.9300
N5—C11	1.450 (3)	C10—H10A	0.9600
C1—H1	0.9300	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C3—C4	1.442 (3)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—C5	1.389 (3)	C11—H11C	0.9600
C2—N1—N2	106.54 (17)	C5—C6—C7	120.83 (19)
C1—N2—N1	106.92 (17)	C5—C6—H6	119.6
C1—N3—C2	104.55 (17)	C7—C6—H6	119.6
C1—N3—N4	124.23 (17)	N5—C7—C8	121.48 (18)
C2—N3—N4	131.21 (17)	N5—C7—C6	121.64 (18)
C3—N4—N3	114.03 (17)	C8—C7—C6	116.88 (18)
C7—N5—C10	121.78 (18)	C9—C8—C7	121.39 (19)
C7—N5—C11	120.24 (17)	C9—C8—H8	119.3
C10—N5—C11	117.98 (18)	C7—C8—H8	119.3
N2—C1—N3	111.1 (2)	C8—C9—C4	121.70 (19)
N2—C1—H1	124.4	C8—C9—H9	119.1
N3—C1—H1	124.4	C4—C9—H9	119.1
N1—C2—N3	110.9 (2)	N5—C10—H10A	109.5
N1—C2—H2	124.6	N5—C10—H10B	109.5
N3—C2—H2	124.6	H10A—C10—H10B	109.5
N4—C3—C4	123.37 (19)	N5—C10—H10C	109.5
N4—C3—H3	118.3	H10A—C10—H10C	109.5
C4—C3—H3	118.3	H10B—C10—H10C	109.5
C5—C4—C9	117.30 (18)	N5—C11—H11A	109.5
C5—C4—C3	123.47 (18)	N5—C11—H11B	109.5
C9—C4—C3	119.19 (18)	H11A—C11—H11B	109.5
C6—C5—C4	121.84 (19)	N5—C11—H11C	109.5
C6—C5—H5	119.1	H11A—C11—H11C	109.5
C4—C5—H5	119.1	H11B—C11—H11C	109.5
C2—N1—N2—C1	0.1 (2)	C3—C4—C5—C6	176.31 (19)
C1—N3—N4—C3	143.42 (19)	C4—C5—C6—C7	−0.5 (3)
C2—N3—N4—C3	−38.0 (3)	C10—N5—C7—C8	−176.5 (2)
N1—N2—C1—N3	−0.3 (2)	C11—N5—C7—C8	3.2 (3)
C2—N3—C1—N2	0.5 (2)	C10—N5—C7—C6	3.8 (3)
N4—N3—C1—N2	179.38 (16)	C11—N5—C7—C6	−176.49 (19)
N2—N1—C2—N3	0.2 (2)	C5—C6—C7—N5	−177.92 (19)
C1—N3—C2—N1	−0.4 (2)	C5—C6—C7—C8	2.4 (3)
N4—N3—C2—N1	−179.24 (17)	N5—C7—C8—C9	177.99 (18)
N3—N4—C3—C4	179.31 (16)	C6—C7—C8—C9	−2.3 (3)
N4—C3—C4—C5	−3.8 (3)	C7—C8—C9—C4	0.4 (3)
N4—C3—C4—C9	173.89 (18)	C5—C4—C9—C8	1.5 (3)
C9—C4—C5—C6	−1.4 (3)	C3—C4—C9—C8	−176.33 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N4i	0.93	2.57	3.448 (3)	157
C2—H2···N2ii	0.93	2.43	3.284 (3)	152
C11—H11B···N1iii	0.96	2.60	3.543 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N4i	0.93	2.57	3.448 (3)	157
C2—H2⋯N2ii	0.93	2.43	3.284 (3)	152
C11—H11B⋯N1iii	0.96	2.60	3.543 (3)	166

Symmetry codes: (i) ; (ii) ; (iii) .