5-[4-(1H-Imidazol-1-yl)phen­yl]-1H-tetra­zole

Tong, S.-W.; Song, W.-D.; Li, S.-J.; Miao, D.-L.; An, J.-B.

doi:10.1107/S1600536812013670

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1274

doi:10.1107/S1600536812013670

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5-[4-(1H-Imidazol-1-yl)phenyl]-1H-tetrazole

Shao-Wei Tong,^a Wen-Dong Song,^b ^* Shi-Jie Li,^c Dong-Liang Miao ^a and Jing-Bo An ^a

^aCollege of Food Science and Technology, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China, ^bCollege of Science, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China, and ^cSchool of Environment Science and Engineering, Donghua University, Shanghai 200051, People's Republic of China
^*Correspondence e-mail: songwd60@163.com

(Received 21 March 2012; accepted 29 March 2012; online 4 April 2012)

In the title compound, C₁₀H₈N₆, the tetrazole and benzene rings are close to being coplanar [dihedral angle = 9.90 (16)°], but the imidazole ring is rotated 37.18 (09)° out of the benzene plane. In the crystal, molecules are connected through tetrazole–imidazole N—H⋯N hydrogen bonds, giving rise to zigzag chains, which extend along [010].

Related literature

For our previous work based on the imidazole derivatives as ligands, see: Li et al. (2010 ); Tong et al. (2011 ); Tong et al., (2012 ). For related structures, see: Huang et al. (2009 ); Cheng (2011 ).

Experimental

Crystal data

C₁₀H₈N₆
M_r = 212.22
Monoclinic, P 2₁
a = 3.7219 (12) Å
b = 16.429 (5) Å
c = 7.791 (2) Å
β = 97.167 (6)°
V = 472.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.971, T_max = 0.985
3477 measured reflections
1421 independent reflections
1239 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.120
S = 1.35
1421 reflections
145 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2ⁱ	0.86	1.93	2.751 (4)	158
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812013670/zs2194sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013670/zs2194Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013670/zs2194Isup3.cml

checkCIF report

Comment top

The imidazole derivatives can be used to synthesize various types of metal complexes because they contain available N-donor sites for coordination. Our research group has shown great interest in metal-organic complexes with imidazole derivatives, e.g. 2-propylimidazole-4,5-dicarboxylic acid (Tong et al., 2011; Li et al., 2010) and 5-[4-imidazol-1-yl)phenyl]tetrazole (1-tetrazole-4-imidazolebenzene) (Tong et al., 2012). In this paper, we report the crystal structure of this ligand from crystals obtained under hydrothermal conditions. As illustrated in Fig. 1, the tetrazole and benzene rings are close to coplanar [dihedral angle, 9.90 (16)°] but the imidazole ring is rotated 37.18 (19)° out of the benzene plane. The molecules are connected into one-dimensional zigzag chains through tetrazole N—H···N_imidazole hydrogen bonds (Table 1, Fig. 2). For the structures of complexes with this ligand, see Huang et al. (2009) and Cheng (2011).

Related literature top

For our previous work based on the imidazole derivatives as ligands, see: Li et al. (2010); Tong et al. (2011); Tong et al., (2012). For related structures, see: Huang et al. (2009); Cheng (2011).

Experimental top

5-[4-imidazol-1-yl)phenyl]tetrazole (0.2 mmol, 0.043 g) in 12 ml of N,N-dimethylformamide was sealed in an autoclave equipped with a Teflon liner (25 ml) and then heated at 413 K for 3 days. Crystals of the title compound were obtained by slow evaporation of the solvent at room temperature.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular conformation and atom numbering scheme for the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The one-dimensional chain structure extending along [010], with hydrogen bonds shown as dashed lines.

5-[4-(1H-Imidazol-1-yl)phenyl]-1H-tetrazole top

Crystal data top

C₁₀H₈N₆	F(000) = 220
M_r = 212.22	D_x = 1.491 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1003 reflections
a = 3.7219 (12) Å	θ = 2.6–22.3°
b = 16.429 (5) Å	µ = 0.10 mm⁻¹
c = 7.791 (2) Å	T = 296 K
β = 97.167 (6)°	Block, colorless
V = 472.6 (3) Å³	0.30 × 0.20 × 0.15 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1421 independent reflections
Radiation source: fine-focus sealed tube	1239 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −4→4
T_min = 0.971, T_max = 0.985	k = −19→18
3477 measured reflections	l = −9→9

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.35	w = 1/[σ²(F_o²) + (0.051P)² + 0.001P] where P = (F_o² + 2F_c²)/3
1421 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₀H₈N₆	V = 472.6 (3) Å³
M_r = 212.22	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 3.7219 (12) Å	µ = 0.10 mm⁻¹
b = 16.429 (5) Å	T = 296 K
c = 7.791 (2) Å	0.30 × 0.20 × 0.15 mm
β = 97.167 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1421 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1239 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.985	R_int = 0.038
3477 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.120	H-atom parameters constrained
S = 1.35	Δρ_max = 0.25 e Å⁻³
1421 reflections	Δρ_min = −0.31 e Å⁻³
145 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.9106 (8)	0.45885 (16)	0.5643 (3)	0.0314 (7)
N2	0.9495 (8)	0.57050 (19)	0.7228 (4)	0.0388 (8)
N3	0.3005 (9)	0.16887 (18)	0.0321 (4)	0.0370 (8)
H3	0.2517	0.1475	0.1273	0.044*
N4	0.2320 (10)	0.13459 (19)	−0.1262 (4)	0.0451 (9)
N5	0.3436 (11)	0.1857 (2)	−0.2329 (4)	0.0487 (9)
N6	0.4867 (9)	0.2536 (2)	−0.1484 (4)	0.0422 (8)
C1	0.6945 (10)	0.3256 (2)	0.4631 (4)	0.0350 (9)
H1A	0.6956	0.3095	0.5776	0.042*
C2	0.5860 (10)	0.2723 (2)	0.3310 (4)	0.0352 (9)
H2A	0.5189	0.2195	0.3563	0.042*
C3	0.5757 (9)	0.2967 (2)	0.1594 (4)	0.0276 (8)
C4	0.6843 (9)	0.3746 (2)	0.1250 (4)	0.0326 (8)
H4A	0.6805	0.3911	0.0106	0.039*
C5	0.7988 (9)	0.4287 (2)	0.2560 (4)	0.0330 (9)
H5A	0.8719	0.4810	0.2308	0.040*
C6	0.8024 (9)	0.4037 (2)	0.4249 (4)	0.0287 (8)
C7	0.8324 (9)	0.5391 (2)	0.5711 (4)	0.0350 (9)
H7A	0.7107	0.5684	0.4796	0.042*
C8	1.1139 (10)	0.5070 (2)	0.8171 (4)	0.0359 (9)
H8A	1.2250	0.5110	0.9305	0.043*
C9	1.0919 (10)	0.4384 (2)	0.7229 (4)	0.0338 (8)
H9A	1.1812	0.3873	0.7578	0.041*
C10	0.4558 (10)	0.2411 (2)	0.0171 (4)	0.0310 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0388 (17)	0.0255 (18)	0.0297 (16)	0.0014 (13)	0.0032 (13)	0.0001 (13)
N2	0.050 (2)	0.0313 (17)	0.0346 (16)	0.0023 (15)	0.0045 (14)	−0.0022 (14)
N3	0.0485 (19)	0.0313 (18)	0.0303 (16)	−0.0028 (15)	0.0015 (14)	0.0012 (13)
N4	0.062 (2)	0.0357 (19)	0.0359 (18)	−0.0056 (17)	0.0009 (15)	−0.0041 (15)
N5	0.074 (3)	0.039 (2)	0.0330 (19)	−0.0032 (18)	0.0052 (18)	−0.0041 (16)
N6	0.059 (2)	0.0367 (18)	0.0318 (16)	−0.0055 (16)	0.0080 (15)	−0.0003 (15)
C1	0.047 (2)	0.032 (2)	0.0268 (19)	0.0006 (18)	0.0065 (16)	0.0046 (15)
C2	0.048 (2)	0.027 (2)	0.0317 (19)	−0.0044 (17)	0.0078 (16)	0.0036 (15)
C3	0.0263 (17)	0.0287 (19)	0.0279 (17)	0.0004 (15)	0.0040 (14)	−0.0004 (15)
C4	0.040 (2)	0.034 (2)	0.0249 (19)	−0.0007 (17)	0.0053 (16)	0.0049 (15)
C5	0.038 (2)	0.028 (2)	0.0338 (19)	−0.0045 (17)	0.0094 (16)	0.0049 (15)
C6	0.0290 (19)	0.0288 (19)	0.0281 (18)	0.0000 (16)	0.0027 (15)	−0.0034 (15)
C7	0.037 (2)	0.033 (2)	0.034 (2)	0.0034 (17)	0.0001 (16)	0.0018 (15)
C8	0.039 (2)	0.040 (2)	0.0278 (17)	0.0008 (18)	0.0023 (15)	0.0000 (17)
C9	0.039 (2)	0.031 (2)	0.0293 (18)	0.0042 (17)	−0.0018 (15)	0.0032 (15)
C10	0.0362 (19)	0.029 (2)	0.0281 (19)	−0.0020 (16)	0.0054 (15)	0.0017 (15)

Geometric parameters (Å, º) top

N1—C7	1.353 (4)	C1—H1A	0.9300
N1—C9	1.374 (4)	C2—C3	1.392 (4)
N1—C6	1.433 (4)	C2—H2A	0.9300
N2—C7	1.313 (4)	C3—C4	1.377 (5)
N2—C8	1.376 (5)	C3—C10	1.463 (4)
N3—C10	1.332 (5)	C4—C5	1.381 (5)
N3—N4	1.351 (4)	C4—H4A	0.9300
N3—H3	0.8600	C5—C6	1.377 (4)
N4—N5	1.286 (5)	C5—H5A	0.9300
N5—N6	1.369 (5)	C7—H7A	0.9300
N6—C10	1.324 (4)	C8—C9	1.342 (5)
C1—C2	1.374 (5)	C8—H8A	0.9300
C1—C6	1.387 (5)	C9—H9A	0.9300

C7—N1—C9	106.7 (3)	C3—C4—H4A	119.2
C7—N1—C6	127.2 (3)	C5—C4—H4A	119.2
C9—N1—C6	125.9 (3)	C6—C5—C4	118.7 (3)
C7—N2—C8	105.0 (3)	C6—C5—H5A	120.7
C10—N3—N4	109.0 (3)	C4—C5—H5A	120.7
C10—N3—H3	125.5	C5—C6—C1	120.8 (3)
N4—N3—H3	125.5	C5—C6—N1	120.2 (3)
N5—N4—N3	106.2 (3)	C1—C6—N1	118.9 (3)
N4—N5—N6	111.0 (3)	N2—C7—N1	111.7 (3)
C10—N6—N5	105.4 (3)	N2—C7—H7A	124.2
C2—C1—C6	119.6 (3)	N1—C7—H7A	124.2
C2—C1—H1A	120.2	C9—C8—N2	110.6 (3)
C6—C1—H1A	120.2	C9—C8—H8A	124.7
C1—C2—C3	120.4 (3)	N2—C8—H8A	124.7
C1—C2—H2A	119.8	C8—C9—N1	106.0 (3)
C3—C2—H2A	119.8	C8—C9—H9A	127.0
C4—C3—C2	118.7 (3)	N1—C9—H9A	127.0
C4—C3—C10	120.1 (3)	N6—C10—N3	108.3 (3)
C2—C3—C10	121.1 (3)	N6—C10—C3	125.9 (3)
C3—C4—C5	121.7 (3)	N3—C10—C3	125.8 (3)

C10—N3—N4—N5	−0.2 (4)	C9—N1—C6—C1	35.1 (5)
N3—N4—N5—N6	0.2 (4)	C8—N2—C7—N1	0.5 (4)
N4—N5—N6—C10	−0.1 (5)	C9—N1—C7—N2	−0.4 (4)
C6—C1—C2—C3	−1.5 (5)	C6—N1—C7—N2	175.1 (3)
C1—C2—C3—C4	1.5 (5)	C7—N2—C8—C9	−0.5 (4)
C1—C2—C3—C10	−179.1 (3)	N2—C8—C9—N1	0.3 (4)
C2—C3—C4—C5	−0.7 (5)	C7—N1—C9—C8	0.0 (4)
C10—C3—C4—C5	179.9 (3)	C6—N1—C9—C8	−175.5 (3)
C3—C4—C5—C6	−0.2 (5)	N5—N6—C10—N3	−0.1 (4)
C4—C5—C6—C1	0.2 (5)	N5—N6—C10—C3	179.3 (3)
C4—C5—C6—N1	−178.4 (3)	N4—N3—C10—N6	0.2 (4)
C2—C1—C6—C5	0.7 (5)	N4—N3—C10—C3	−179.2 (3)
C2—C1—C6—N1	179.2 (3)	C4—C3—C10—N6	10.2 (6)
C7—N1—C6—C5	39.0 (5)	C2—C3—C10—N6	−169.2 (4)
C9—N1—C6—C5	−146.3 (3)	C4—C3—C10—N3	−170.6 (3)
C7—N1—C6—C1	−139.6 (4)	C2—C3—C10—N3	10.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2ⁱ	0.86	1.93	2.751 (4)	158

Symmetry code: (i) −x+1, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₆
M_r	212.22
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	3.7219 (12), 16.429 (5), 7.791 (2)
β (°)	97.167 (6)
V (Å³)	472.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.971, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	3477, 1421, 1239
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.120, 1.35
No. of reflections	1421
No. of parameters	145
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.31

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2ⁱ	0.86	1.93	2.751 (4)	157.9

Symmetry code: (i) −x+1, y−1/2, −z+1.

Acknowledgements

We acknowledge the Public Science and Technology Research Funds Projects of Ocean (grant No. 2000905021), the Guangdong Oceanic Fisheries Technology Promotion Project [grant No. A2009003–018(c)], the Guangdong Chinese Academy of Science Comprehensive Strategic Cooperation Project (grant No. 2009B091300121) and the Guangdong Province Key Project in the Field of Social Development [grant No. A2009011–007(c)].

References

Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cheng, X.-C. (2011). Acta Cryst. E67, m1757. Web of Science CSD CrossRef IUCr Journals Google Scholar
Huang, R.-Y., Zhu, K., Chen, H., Liu, G.-X. & Ren, X.-M. (2009). Wuji Huaxue Xuebao, 25, 162–165. CAS Google Scholar
Li, S.-J., Miao, D.-L., Song, W.-D., Li, S.-H. & Yan, J.-B. (2010). Acta Cryst. E66, m1096–m1097. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tong, S.-W., Li, S.-J., Song, W.-D., Miao, D.-L. & An, J.-B. (2011). Acta Cryst. E67, m1870–m1871. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tong, S.-W., Song, W.-D., Miao, D.-L., Li, S.-J. & An, J.-B. (2012). Acta Cryst. E68, m433–m434. CSD CrossRef IUCr Journals Google Scholar