4-[5-(3-Pyrid­yl)-2H-tetra­zol-2-ylmeth­yl]benzonitrile

Hu, B.

doi:10.1107/S1600536808009550

organic compounds

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Volume 64| Part 6| June 2008| Page o973

doi:10.1107/S1600536808009550

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4-[5-(3-Pyridyl)-2H-tetrazol-2-ylmethyl]benzonitrile

Bin Hu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fudavid88@yahoo.com.cn

(Received 28 March 2008; accepted 7 April 2008; online 3 May 2008)

In the title compound, C₁₄H₁₀N₆, the pyridine and tetrazole rings are nearly coplanar and are twisted from each other by a dihedral angle of only 0.86 (9)°. The benzene ring makes a dihedral angle of 70.55 (6)° with the tetrazole ring.

Related literature

For the use of tetrazole derivatives in coordination chemisty, see: Arp et al. (2000 ); Hu et al. (2007 ); Wang et al. (2005 ); Xiong et al. (2002 ).

Experimental

Crystal data

C₁₄H₁₀N₆
M_r = 262.28
Triclinic, $[P \overline 1]$
a = 8.0452 (16) Å
b = 8.7081 (17) Å
c = 10.171 (2) Å
α = 94.61 (3)°
β = 104.95 (3)°
γ = 111.11 (3)°
V = 630.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.4 × 0.35 × 0.35 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.962, T_max = 0.968
6638 measured reflections
2882 independent reflections
2063 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.123
S = 1.04
2882 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009550/dn2333sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009550/dn2333Isup2.hkl

checkCIF report

Comment top

In the past five years, we have focused on the chemistry of tetrazole derivatives because of their multiple coordination modes as ligands to metal ions and for the construction of novel metal-organic frameworks (Wang et al., 2005; Xiong et al., 2002). We report here the crystal structure of the title compound, 4-((5-(pyridin-3-yl)-2H-tetrazol-2-yl)methyl)benzonitrile.

There are three rings in the title compound (Fig. 1). The pyridine and tetrazole rings are nearly coplanar and are twisted from each other by a dihedral angle of only 0.86 (0.09) °.The benzene ring makes a dihedral angle of 70.55 (0.06) ° with the tetrazole ring owing to the methylene bridge which forces the two rings to be twisted twisted from each other. In the pyridine ring, the C1=N1 and C5=N1 bond distance of 1.322 and 1.332Å conforms to the value for a C=N double bond, while the C14—N6 bond length of 1.140 Å conforms to the value for a C≡N bond. The bond distances and bond angles of the tetrazole rings are within the usual ranges (Wang et al., 2005; Arp et al., 2000; Hu et al., 2007).

Related literature top

For use of tetrazole derivatives in coordination chemisty, see: Arp et al. (2000); Hu et al. (2007); Wang et al. (2005); Xiong et al. (2002).

Experimental top

4-((5-(pyridin-3-yl)-2H-tetrazol-2-yl)methyl)benzonitrile (3 mmol) was dissolved in ethanol (20 ml) and evaporated in the air affording colorless block crystals of this compound suitable for X-ray analysis were obtained.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

4-[5-(3-Pyridyl)-2H-tetrazol-2-ylmethyl]benzonitrile top

Crystal data top

C₁₄H₁₀N₆	Z = 2
M_r = 262.28	F(000) = 272
Triclinic, P1	D_x = 1.382 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0452 (16) Å	Cell parameters from 2882 reflections
b = 8.7081 (17) Å	θ = 3.4–27.5°
c = 10.171 (2) Å	µ = 0.09 mm⁻¹
α = 94.61 (3)°	T = 293 K
β = 104.95 (3)°	Block, colourless
γ = 111.11 (3)°	0.4 × 0.35 × 0.35 mm
V = 630.3 (3) Å³

Data collection top

Rigaku Mercury2 diffractometer	2882 independent reflections
Radiation source: fine-focus sealed tube	2063 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
T_min = 0.962, T_max = 0.968	l = −13→13
6638 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0473P)² + 0.0983P] where P = (F_o² + 2F_c²)/3
2882 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₄H₁₀N₆	γ = 111.11 (3)°
M_r = 262.28	V = 630.3 (3) Å³
Triclinic, P1	Z = 2
a = 8.0452 (16) Å	Mo Kα radiation
b = 8.7081 (17) Å	µ = 0.09 mm⁻¹
c = 10.171 (2) Å	T = 293 K
α = 94.61 (3)°	0.4 × 0.35 × 0.35 mm
β = 104.95 (3)°

Data collection top

Rigaku Mercury2 diffractometer	2882 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2063 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.968	R_int = 0.035
6638 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.04	Δρ_max = 0.17 e Å⁻³
2882 reflections	Δρ_min = −0.20 e Å⁻³
181 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.1058 (3)	−0.1591 (2)	0.5558 (2)	0.0572 (5)
H1	0.0253	−0.2512	0.5801	0.069*
C2	0.2506 (3)	−0.0395 (2)	0.65976 (19)	0.0573 (5)
H2	0.2661	−0.0497	0.7520	0.069*
C3	0.3732 (2)	0.0965 (2)	0.62507 (17)	0.0492 (4)
H3	0.4736	0.1790	0.6936	0.059*
C4	0.3447 (2)	0.10834 (19)	0.48717 (15)	0.0379 (3)
C5	0.1926 (2)	−0.0186 (2)	0.39132 (18)	0.0503 (4)
H5	0.1717	−0.0109	0.2983	0.060*
C6	0.4708 (2)	0.24879 (19)	0.44434 (15)	0.0389 (4)
C7	0.6451 (3)	0.4856 (2)	0.2136 (2)	0.0558 (5)
H7A	0.7176	0.6053	0.2454	0.067*
H7B	0.5309	0.4698	0.1420	0.067*
C8	0.7564 (2)	0.4087 (2)	0.15309 (17)	0.0443 (4)
C9	0.9485 (2)	0.4701 (2)	0.21250 (18)	0.0493 (4)
H9	1.0070	0.5578	0.2888	0.059*
C10	1.0544 (2)	0.4029 (2)	0.16004 (17)	0.0474 (4)
H10	1.1835	0.4445	0.2011	0.057*
C11	0.9677 (2)	0.2733 (2)	0.04600 (16)	0.0417 (4)
C12	0.7746 (2)	0.2088 (2)	−0.01356 (17)	0.0513 (4)
H12	0.7162	0.1201	−0.0892	0.062*
C13	0.6696 (2)	0.2767 (2)	0.03990 (18)	0.0523 (4)
H13	0.5403	0.2340	0.0000	0.063*
C14	1.0826 (2)	0.2107 (2)	−0.01146 (17)	0.0490 (4)
N1	0.0737 (2)	−0.15148 (18)	0.42275 (17)	0.0583 (4)
N2	0.45326 (18)	0.26697 (17)	0.31385 (13)	0.0448 (3)
N3	0.59763 (19)	0.41048 (17)	0.32955 (14)	0.0455 (3)
N4	0.6996 (2)	0.47768 (19)	0.45939 (16)	0.0551 (4)
N5	0.61961 (19)	0.37565 (18)	0.53498 (14)	0.0514 (4)
N6	1.1781 (2)	0.1676 (2)	−0.05615 (16)	0.0654 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0591 (11)	0.0495 (10)	0.0713 (13)	0.0216 (9)	0.0306 (10)	0.0206 (9)
C2	0.0666 (12)	0.0641 (12)	0.0495 (10)	0.0281 (10)	0.0255 (9)	0.0203 (9)
C3	0.0496 (10)	0.0522 (10)	0.0430 (9)	0.0188 (8)	0.0125 (8)	0.0065 (7)
C4	0.0371 (8)	0.0419 (8)	0.0386 (8)	0.0188 (7)	0.0144 (7)	0.0053 (6)
C5	0.0526 (10)	0.0491 (10)	0.0444 (9)	0.0150 (8)	0.0159 (8)	0.0054 (7)
C6	0.0354 (8)	0.0438 (9)	0.0394 (8)	0.0169 (7)	0.0140 (7)	0.0029 (7)
C7	0.0618 (11)	0.0595 (11)	0.0698 (12)	0.0333 (10)	0.0402 (10)	0.0299 (9)
C8	0.0468 (9)	0.0490 (9)	0.0487 (9)	0.0224 (8)	0.0255 (8)	0.0201 (8)
C9	0.0491 (10)	0.0486 (10)	0.0475 (9)	0.0146 (8)	0.0186 (8)	0.0044 (8)
C10	0.0364 (8)	0.0534 (10)	0.0496 (9)	0.0144 (8)	0.0144 (8)	0.0074 (8)
C11	0.0406 (9)	0.0491 (9)	0.0384 (8)	0.0182 (7)	0.0154 (7)	0.0109 (7)
C12	0.0438 (9)	0.0598 (11)	0.0427 (9)	0.0165 (8)	0.0093 (8)	0.0009 (8)
C13	0.0371 (9)	0.0664 (11)	0.0541 (10)	0.0197 (8)	0.0157 (8)	0.0137 (9)
C14	0.0450 (9)	0.0571 (10)	0.0426 (9)	0.0189 (8)	0.0125 (8)	0.0064 (8)
N1	0.0565 (9)	0.0442 (8)	0.0663 (10)	0.0107 (7)	0.0201 (8)	0.0074 (7)
N2	0.0430 (8)	0.0487 (8)	0.0437 (8)	0.0157 (6)	0.0188 (6)	0.0089 (6)
N3	0.0428 (8)	0.0474 (8)	0.0531 (8)	0.0184 (7)	0.0246 (7)	0.0121 (7)
N4	0.0447 (8)	0.0538 (9)	0.0591 (9)	0.0095 (7)	0.0194 (7)	0.0059 (7)
N5	0.0437 (8)	0.0523 (8)	0.0502 (8)	0.0097 (7)	0.0162 (7)	0.0055 (7)
N6	0.0581 (10)	0.0839 (12)	0.0611 (10)	0.0351 (9)	0.0227 (8)	0.0040 (9)

Geometric parameters (Å, º) top

C1—N1	1.322 (2)	C7—H7B	0.9700
C1—C2	1.369 (3)	C8—C9	1.382 (2)
C1—H1	0.9300	C8—C13	1.389 (3)
C2—C3	1.381 (3)	C9—C10	1.377 (2)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.380 (2)	C10—C11	1.383 (2)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.381 (2)	C11—C12	1.389 (2)
C4—C6	1.461 (2)	C11—C14	1.443 (2)
C5—N1	1.332 (2)	C12—C13	1.380 (2)
C5—H5	0.9300	C12—H12	0.9300
C6—N2	1.3265 (19)	C13—H13	0.9300
C6—N5	1.348 (2)	C14—N6	1.140 (2)
C7—N3	1.464 (2)	N2—N3	1.3277 (19)
C7—C8	1.509 (2)	N3—N4	1.315 (2)
C7—H7A	0.9700	N4—N5	1.322 (2)

N1—C1—C2	123.89 (17)	C9—C8—C7	119.23 (16)
N1—C1—H1	118.1	C13—C8—C7	121.38 (16)
C2—C1—H1	118.1	C10—C9—C8	120.79 (16)
C1—C2—C3	118.73 (17)	C10—C9—H9	119.6
C1—C2—H2	120.6	C8—C9—H9	119.6
C3—C2—H2	120.6	C9—C10—C11	119.63 (15)
C4—C3—C2	119.00 (17)	C9—C10—H10	120.2
C4—C3—H3	120.5	C11—C10—H10	120.2
C2—C3—H3	120.5	C10—C11—C12	120.21 (15)
C3—C4—C5	117.22 (15)	C10—C11—C14	118.62 (15)
C3—C4—C6	121.38 (15)	C12—C11—C14	121.14 (15)
C5—C4—C6	121.40 (14)	C13—C12—C11	119.73 (16)
N1—C5—C4	124.61 (16)	C13—C12—H12	120.1
N1—C5—H5	117.7	C11—C12—H12	120.1
C4—C5—H5	117.7	C12—C13—C8	120.24 (16)
N2—C6—N5	112.35 (14)	C12—C13—H13	119.9
N2—C6—C4	124.60 (14)	C8—C13—H13	119.9
N5—C6—C4	123.05 (14)	N6—C14—C11	177.31 (19)
N3—C7—C8	111.58 (13)	C1—N1—C5	116.53 (16)
N3—C7—H7A	109.3	C6—N2—N3	101.60 (13)
C8—C7—H7A	109.3	N4—N3—N2	114.04 (13)
N3—C7—H7B	109.3	N4—N3—C7	122.32 (15)
C8—C7—H7B	109.3	N2—N3—C7	123.60 (15)
H7A—C7—H7B	108.0	N3—N4—N5	106.02 (13)
C9—C8—C13	119.38 (16)	N4—N5—C6	105.98 (13)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₆
M_r	262.28
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.0452 (16), 8.7081 (17), 10.171 (2)
α, β, γ (°)	94.61 (3), 104.95 (3), 111.11 (3)
V (Å³)	630.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.4 × 0.35 × 0.35

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.962, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	6638, 2882, 2063
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.123, 1.04
No. of reflections	2882
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

This work was supported by a Start-up Grant from Southeast University to Professor Ren-Gen Xiong.

References

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