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

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.124
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C14     ..       6.19 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C11    -   C14    ...       1.44 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

All H atoms were fixed geometrically and treated as riding with C–H = 0.93 Å (aromatic) and 0.97 Å (methylene) with U_iso(H) =1.2Ueq(C).

Computing details

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

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

Crystal data

C14H10N6	Z = 2
Mr = 262.28	F(000) = 272
Triclinic, P1	Dx = 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) Å^3

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0473P)^2 + 0.0983P] where P = (Fo^2 + 2Fc^2)/3
2882 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)