1-[2-(1H-Benzimidazol-2-yl)eth-yl]-1H-1,2,3-benzotriazole.

In the title compound, C(15)H(13)N(5), the N-containing heterocycles are linked by an ethyl-ene spacer in a gauche conformation, the N-C-C-C torsion angle along the linker being 60.1 (3)°. The dihedral angle between the terminal benzotriazole and benzimidazole rings is 39.02 (6)°. In the crystal, adjacent mol-ecules are connected by N-H⋯N hydrogen bonds, forming an infinite chain along the c axis. π-π stacking inter-actions [centroid-centroid distance = 3.8772 (7) Å] between the benzotriazole rings of neighbouring chains extend these chains into a supra-molecular sheet in the bc plane. Weak inter-molecular C-H⋯N inter-actions further stabilize the crystal structure.

Related literature

For the synthesis and anti­viral activity of bis-heterocyclcic compounds containing both benzotriazole and benzimidazole, see: Pagani & Sparatore (1965 ▶); Paglietti et al. (1975 ▶); Katritzky et al. (1996 ▶); Yu et al. (2003 ▶); Tonelli et al. (2008 ▶). For the crystal structure of 1-(benzimidazol-2-ylmeth­yl)-1H-benzotriazole, see: Liu et al. (2007 ▶).

Experimental

Crystal data

C15H13N5

M = 263.30

Monoclinic,

a = 6.3510 (13) Å

b = 20.830 (4) Å

c = 9.901 (2) Å

β = 96.78 (3)°

V = 1300.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 K

0.37 × 0.32 × 0.26 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001) ▶ T min = 0.969, T max = 0.978

10985 measured reflections

2290 independent reflections

1608 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.125

S = 1.01

2290 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811045442/zj2029sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045442/zj2029Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045442/zj2029Isup3.cml

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

C15H13N5	F(000) = 552
Mr = 263.30	Dx = 1.345 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10162 reflections
a = 6.3510 (13) Å	θ = 3.2–27.8°
b = 20.830 (4) Å	µ = 0.09 mm−1
c = 9.901 (2) Å	T = 294 K
β = 96.78 (3)°	Block, colourless
V = 1300.7 (5) Å3	0.37 × 0.32 × 0.26 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	2290 independent reflections
Radiation source: fine-focus sealed tube	1608 reflections with I > 2σ(I)
graphite	Rint = 0.071
phi and ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
Tmin = 0.969, Tmax = 0.978	k = −24→24
10985 measured reflections	l = −11→11

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.040P)2 + 0.8P] where P = (Fo2 + 2Fc2)/3
2290 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
C1	−0.2105 (4)	0.96993 (13)	0.3185 (3)	0.0476 (7)
H1	−0.3426	0.9620	0.3468	0.057*
C2	−0.1838 (5)	1.01290 (14)	0.2171 (3)	0.0573 (8)
H2	−0.3016	1.0346	0.1748	0.069*
C3	0.0144 (5)	1.02507 (15)	0.1755 (3)	0.0567 (8)
H3	0.0252	1.0549	0.1068	0.068*
C4	0.1916 (5)	0.99482 (14)	0.2323 (3)	0.0539 (8)
H4	0.3230	1.0028	0.2029	0.065*
C5	0.1695 (4)	0.95122 (13)	0.3364 (3)	0.0414 (7)
C6	−0.0285 (4)	0.93888 (12)	0.3764 (3)	0.0367 (6)
C7	−0.1427 (4)	0.85935 (13)	0.5476 (3)	0.0448 (7)
H7A	−0.2662	0.8860	0.5547	0.054*
H7B	−0.0790	0.8493	0.6391	0.054*
C8	−0.2120 (4)	0.79717 (13)	0.4733 (3)	0.0435 (7)
H8A	−0.3149	0.7754	0.5220	0.052*
H8B	−0.2801	0.8074	0.3830	0.052*
C9	−0.0301 (4)	0.75382 (12)	0.4618 (2)	0.0344 (6)
C10	0.4117 (5)	0.65844 (13)	0.5972 (3)	0.0482 (7)
H10	0.4180	0.6501	0.6899	0.058*
C11	0.5649 (5)	0.63636 (13)	0.5222 (3)	0.0526 (8)
H11	0.6778	0.6127	0.5648	0.063*
C12	0.5546 (5)	0.64870 (13)	0.3839 (3)	0.0498 (8)
H12	0.6615	0.6333	0.3361	0.060*
C13	0.3915 (4)	0.68287 (13)	0.3161 (3)	0.0438 (7)
H13	0.3856	0.6904	0.2232	0.053*
C14	0.2348 (4)	0.70614 (12)	0.3900 (2)	0.0344 (6)
C15	0.2474 (4)	0.69362 (12)	0.5293 (2)	0.0363 (6)
N1	0.0085 (3)	0.89470 (10)	0.4772 (2)	0.0388 (6)
N2	0.2169 (4)	0.87999 (11)	0.4968 (2)	0.0491 (6)
N3	0.3165 (3)	0.91386 (12)	0.4137 (3)	0.0530 (7)
N4	0.0740 (3)	0.72406 (10)	0.5709 (2)	0.0398 (6)
H14	0.0439	0.7286	0.6512	0.060*
N5	0.0578 (3)	0.74388 (10)	0.3498 (2)	0.0379 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0375 (16)	0.0444 (17)	0.0615 (19)	−0.0022 (14)	0.0082 (14)	−0.0019 (15)
C2	0.0480 (19)	0.0470 (19)	0.074 (2)	0.0052 (15)	−0.0048 (16)	0.0073 (18)
C3	0.060 (2)	0.0481 (18)	0.061 (2)	−0.0064 (16)	0.0035 (17)	0.0156 (16)
C4	0.0446 (18)	0.0541 (19)	0.065 (2)	−0.0064 (15)	0.0167 (16)	0.0090 (17)
C5	0.0365 (15)	0.0413 (16)	0.0473 (17)	−0.0015 (13)	0.0086 (13)	−0.0024 (14)
C6	0.0373 (16)	0.0330 (15)	0.0399 (16)	−0.0013 (12)	0.0045 (13)	−0.0062 (13)
C7	0.0474 (17)	0.0458 (17)	0.0440 (17)	−0.0007 (14)	0.0173 (14)	−0.0020 (14)
C8	0.0403 (16)	0.0504 (17)	0.0411 (16)	−0.0085 (14)	0.0103 (13)	−0.0003 (14)
C9	0.0388 (15)	0.0400 (15)	0.0247 (14)	−0.0109 (12)	0.0045 (12)	−0.0014 (12)
C10	0.0574 (19)	0.0471 (17)	0.0390 (16)	−0.0050 (15)	0.0007 (15)	0.0113 (14)
C11	0.0498 (19)	0.0397 (17)	0.067 (2)	0.0042 (14)	0.0008 (16)	0.0082 (16)
C12	0.0539 (19)	0.0389 (17)	0.059 (2)	0.0011 (15)	0.0152 (16)	−0.0045 (15)
C13	0.0539 (18)	0.0435 (17)	0.0349 (15)	−0.0027 (14)	0.0092 (14)	−0.0063 (13)
C14	0.0454 (16)	0.0332 (14)	0.0249 (13)	−0.0068 (13)	0.0057 (12)	−0.0048 (12)
C15	0.0455 (16)	0.0321 (15)	0.0317 (14)	−0.0060 (13)	0.0063 (13)	−0.0012 (12)
N1	0.0346 (13)	0.0403 (13)	0.0422 (13)	−0.0008 (10)	0.0072 (10)	0.0007 (11)
N2	0.0369 (14)	0.0555 (16)	0.0547 (15)	0.0026 (12)	0.0045 (12)	0.0074 (13)
N3	0.0338 (13)	0.0617 (16)	0.0645 (17)	−0.0004 (12)	0.0099 (12)	0.0116 (14)
N4	0.0486 (14)	0.0480 (14)	0.0240 (12)	−0.0074 (11)	0.0095 (10)	−0.0008 (10)
N5	0.0419 (13)	0.0465 (13)	0.0257 (11)	−0.0022 (11)	0.0057 (10)	0.0004 (10)

C1—C2	1.370 (4)	C8—H8B	0.9700
C1—C6	1.388 (4)	C9—N5	1.316 (3)
C1—H1	0.9300	C9—N4	1.348 (3)
C2—C3	1.393 (4)	C10—C11	1.372 (4)
C2—H2	0.9300	C10—C15	1.383 (4)
C3—C4	1.353 (4)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.387 (4)
C4—C5	1.394 (4)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.366 (4)
C5—N3	1.376 (3)	C12—H12	0.9300
C5—C6	1.386 (3)	C13—C14	1.391 (3)
C6—N1	1.357 (3)	C13—H13	0.9300
C7—N1	1.453 (3)	C14—N5	1.391 (3)
C7—C8	1.529 (4)	C14—C15	1.397 (3)
C7—H7A	0.9700	C15—N4	1.375 (3)
C7—H7B	0.9700	N1—N2	1.350 (3)
C8—C9	1.481 (4)	N2—N3	1.303 (3)
C8—H8A	0.9700	N4—H14	0.8453
C2—C1—C6	116.0 (3)	N5—C9—N4	112.7 (2)
C2—C1—H1	122.0	N5—C9—C8	125.0 (2)
C6—C1—H1	122.0	N4—C9—C8	122.1 (2)
C1—C2—C3	122.0 (3)	C11—C10—C15	117.2 (3)
C1—C2—H2	119.0	C11—C10—H10	121.4
C3—C2—H2	119.0	C15—C10—H10	121.4
C4—C3—C2	121.9 (3)	C10—C11—C12	121.3 (3)
C4—C3—H3	119.0	C10—C11—H11	119.4
C2—C3—H3	119.0	C12—C11—H11	119.4
C3—C4—C5	117.3 (3)	C13—C12—C11	121.8 (3)
C3—C4—H4	121.3	C13—C12—H12	119.1
C5—C4—H4	121.3	C11—C12—H12	119.1
N3—C5—C6	108.4 (2)	C12—C13—C14	118.1 (3)
N3—C5—C4	131.2 (3)	C12—C13—H13	120.9
C6—C5—C4	120.4 (3)	C14—C13—H13	120.9
N1—C6—C5	104.6 (2)	C13—C14—N5	130.6 (2)
N1—C6—C1	133.1 (2)	C13—C14—C15	119.6 (2)
C5—C6—C1	122.3 (3)	N5—C14—C15	109.8 (2)
N1—C7—C8	111.6 (2)	N4—C15—C10	133.1 (2)
N1—C7—H7A	109.3	N4—C15—C14	104.8 (2)
C8—C7—H7A	109.3	C10—C15—C14	122.1 (3)
N1—C7—H7B	109.3	N2—N1—C6	109.9 (2)
C8—C7—H7B	109.3	N2—N1—C7	120.6 (2)
H7A—C7—H7B	108.0	C6—N1—C7	129.0 (2)
C9—C8—C7	111.8 (2)	N3—N2—N1	109.1 (2)
C9—C8—H8A	109.3	N2—N3—C5	108.0 (2)
C7—C8—H8A	109.3	C9—N4—C15	107.9 (2)
C9—C8—H8B	109.3	C9—N4—H14	124.0
C7—C8—H8B	109.3	C15—N4—H14	127.7
H8A—C8—H8B	107.9	C9—N5—C14	104.9 (2)
C6—C1—C2—C3	−0.5 (4)	N5—C14—C15—N4	0.5 (3)
C1—C2—C3—C4	0.5 (5)	C13—C14—C15—C10	−0.1 (4)
C2—C3—C4—C5	−0.9 (5)	N5—C14—C15—C10	−178.3 (2)
C3—C4—C5—N3	−179.5 (3)	C5—C6—N1—N2	−0.8 (3)
C3—C4—C5—C6	1.5 (4)	C1—C6—N1—N2	−179.3 (3)
N3—C5—C6—N1	0.4 (3)	C5—C6—N1—C7	−173.1 (2)
C4—C5—C6—N1	179.6 (2)	C1—C6—N1—C7	8.4 (5)
N3—C5—C6—C1	179.1 (2)	C8—C7—N1—N2	−83.6 (3)
C4—C5—C6—C1	−1.7 (4)	C8—C7—N1—C6	88.0 (3)
C2—C1—C6—N1	179.4 (3)	C6—N1—N2—N3	1.0 (3)
C2—C1—C6—C5	1.2 (4)	C7—N1—N2—N3	174.1 (2)
N1—C7—C8—C9	60.1 (3)	N1—N2—N3—C5	−0.7 (3)
C7—C8—C9—N5	−105.2 (3)	C6—C5—N3—N2	0.2 (3)
C7—C8—C9—N4	69.2 (3)	C4—C5—N3—N2	−178.9 (3)
C15—C10—C11—C12	−0.2 (4)	N5—C9—N4—C15	1.9 (3)
C10—C11—C12—C13	−0.4 (4)	C8—C9—N4—C15	−173.2 (2)
C11—C12—C13—C14	0.8 (4)	C10—C15—N4—C9	177.2 (3)
C12—C13—C14—N5	177.2 (3)	C14—C15—N4—C9	−1.4 (3)
C12—C13—C14—C15	−0.5 (4)	N4—C9—N5—C14	−1.5 (3)
C11—C10—C15—N4	−177.9 (3)	C8—C9—N5—C14	173.4 (2)
C11—C10—C15—C14	0.5 (4)	C13—C14—N5—C9	−177.3 (3)
C13—C14—C15—N4	178.7 (2)	C15—C14—N5—C9	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H14···N5i	0.84	2.04	2.855 (3)	162
C1—H1···N3ii	0.93	2.54	3.456 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H14⋯N5i	0.84	2.04	2.855 (3)	162
C1—H1⋯N3ii	0.93	2.54	3.456 (3)	167

Symmetry codes: (i) ; (ii) .