1-(2,2-Diphenyl-eth-yl)-1H-tetra-zole.

The crystal structure of the title compound, C(15)H(14)N(4), contains chains of coplanar tetra-zole rings with the chain direction along b. These are formed through weak hydrogen bonds, donated by the tetra-zole H atoms and by one of the H atoms of the methyl-ene group, and accepted by two neighbouring N atoms of the adjacent tetra-zole ring. The chains are connected to each other in a staircase-like manner via weak hydrogen bonds, donated from the second H atom of the methyl-ene group and accepted by the N atom next to the C atom in the tetra-zole ring. The resulting layers are parallel to the bc plane.

Related literature

For the synthesis, see Kamiya & Saito (1973 ▶). For crystal structure studies of 1H-tetra­zol-1-yl compounds, see Absmeier et al. (2006 ▶); Grunert et al. (2005 ▶); Werner et al. (2009 ▶).

Experimental

Crystal data

C15H14N4

M = 250.30

Monoclinic,

a = 12.5289 (6) Å

b = 10.4157 (5) Å

c = 11.0085 (5) Å

β = 107.906 (1)°

V = 1366.99 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.45 × 0.40 × 0.35 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008b ▶) T min = 0.89, T max = 0.97

18385 measured reflections

3984 independent reflections

3230 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.148

S = 1.04

3984 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008a ▶); molecular graphics: ATOMS (Dowty, 2006 ▶), Mercury (Macrae et al., 2006 ▶) and VESTA (Momma & Izumi, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027675/fj2563sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027675/fj2563Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027675/fj2563Isup3.cml

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

C15H14N4	F(000) = 528
Mr = 250.30	Dx = 1.216 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8429 reflections
a = 12.5289 (6) Å	θ = 2.6–30.0°
b = 10.4157 (5) Å	µ = 0.08 mm−1
c = 11.0085 (5) Å	T = 296 K
β = 107.906 (1)°	Block, colourless
V = 1366.99 (11) Å3	0.45 × 0.40 × 0.35 mm
Z = 4

Bruker APEXII CCD diffractometer	3984 independent reflections
Radiation source: fine-focus sealed tube	3230 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 30.1°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b)	h = −17→17
Tmin = 0.89, Tmax = 0.97	k = −14→14
18385 measured reflections	l = −15→15

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0655P)2 + 0.2149P] where P = (Fo2 + 2Fc2)/3
3984 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Experimental. Bruker Kappa APEX2 CCD diffractometer, full-sphere data collection.

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	0.06288 (8)	0.25473 (9)	0.39090 (9)	0.0503 (2)
N2	0.07582 (12)	0.13614 (12)	0.43964 (12)	0.0755 (4)
N3	0.03463 (12)	0.05898 (12)	0.34413 (14)	0.0804 (4)
N4	−0.00552 (11)	0.12529 (13)	0.23470 (12)	0.0724 (3)
C1	0.01312 (12)	0.24583 (14)	0.26661 (13)	0.0630 (3)
H1	−0.0057	0.3149	0.2105	0.076*
C2	0.09677 (9)	0.36869 (11)	0.47103 (11)	0.0493 (2)
H2A	0.0581	0.3693	0.5351	0.059*
H2B	0.0740	0.4448	0.4186	0.059*
C3	0.22336 (9)	0.37415 (10)	0.53767 (10)	0.0464 (2)
H3	0.2443	0.2965	0.5899	0.056*
C4	0.24642 (9)	0.48874 (12)	0.62769 (11)	0.0506 (3)
C5	0.29138 (12)	0.47133 (17)	0.75794 (13)	0.0707 (4)
H5	0.3081	0.3892	0.7915	0.085*
C6	0.31156 (15)	0.5784 (2)	0.83910 (16)	0.0925 (6)
H6	0.3422	0.5670	0.9268	0.111*
C7	0.28658 (15)	0.6999 (2)	0.7905 (2)	0.0903 (6)
H7	0.3007	0.7703	0.8451	0.108*
C8	0.24121 (13)	0.71720 (16)	0.66276 (19)	0.0804 (5)
H8	0.2235	0.7995	0.6300	0.096*
C9	0.22120 (11)	0.61269 (12)	0.58099 (14)	0.0617 (3)
H9	0.1904	0.6257	0.4936	0.074*
C10	0.29411 (8)	0.37823 (10)	0.44771 (10)	0.0458 (2)
C11	0.40353 (11)	0.33206 (17)	0.49185 (14)	0.0722 (4)
H11	0.4298	0.2966	0.5732	0.087*
C12	0.47312 (12)	0.3379 (2)	0.41749 (19)	0.0919 (6)
H12	0.5460	0.3068	0.4490	0.110*
C13	0.43670 (13)	0.38890 (17)	0.29785 (18)	0.0805 (5)
H13	0.4848	0.3937	0.2483	0.097*
C14	0.32823 (14)	0.43332 (14)	0.25067 (15)	0.0701 (4)
H14	0.3024	0.4666	0.1684	0.084*
C15	0.25730 (11)	0.42836 (12)	0.32603 (12)	0.0563 (3)
H15	0.1843	0.4592	0.2940	0.068*

	U11	U22	U33	U12	U13	U23
N1	0.0485 (5)	0.0525 (5)	0.0533 (5)	−0.0114 (4)	0.0206 (4)	−0.0081 (4)
N2	0.0969 (9)	0.0575 (6)	0.0699 (7)	−0.0239 (6)	0.0225 (6)	−0.0022 (5)
N3	0.0952 (9)	0.0597 (7)	0.0895 (9)	−0.0277 (6)	0.0329 (7)	−0.0172 (6)
N4	0.0727 (7)	0.0758 (8)	0.0703 (7)	−0.0213 (6)	0.0242 (6)	−0.0241 (6)
C1	0.0632 (7)	0.0674 (8)	0.0556 (7)	−0.0093 (6)	0.0141 (5)	−0.0115 (6)
C2	0.0484 (5)	0.0522 (6)	0.0515 (6)	−0.0071 (4)	0.0214 (4)	−0.0102 (4)
C3	0.0499 (5)	0.0438 (5)	0.0453 (5)	−0.0031 (4)	0.0146 (4)	−0.0017 (4)
C4	0.0465 (5)	0.0573 (6)	0.0506 (5)	−0.0084 (4)	0.0189 (4)	−0.0114 (5)
C5	0.0712 (8)	0.0886 (10)	0.0520 (7)	−0.0096 (7)	0.0186 (6)	−0.0095 (7)
C6	0.0856 (11)	0.1339 (18)	0.0576 (8)	−0.0170 (11)	0.0215 (7)	−0.0333 (10)
C7	0.0762 (9)	0.0991 (13)	0.0996 (13)	−0.0139 (9)	0.0326 (9)	−0.0541 (11)
C8	0.0698 (8)	0.0656 (8)	0.1080 (13)	−0.0083 (7)	0.0306 (8)	−0.0332 (8)
C9	0.0611 (7)	0.0550 (7)	0.0701 (8)	−0.0065 (5)	0.0217 (6)	−0.0131 (6)
C10	0.0442 (5)	0.0420 (5)	0.0521 (5)	−0.0029 (4)	0.0164 (4)	−0.0079 (4)
C11	0.0502 (6)	0.0951 (11)	0.0667 (8)	0.0103 (6)	0.0110 (6)	−0.0048 (7)
C12	0.0472 (7)	0.1337 (16)	0.0969 (12)	0.0088 (8)	0.0253 (7)	−0.0167 (11)
C13	0.0695 (8)	0.0884 (11)	0.1028 (12)	−0.0155 (7)	0.0549 (9)	−0.0259 (9)
C14	0.0884 (10)	0.0626 (8)	0.0741 (8)	−0.0027 (7)	0.0470 (7)	0.0009 (6)
C15	0.0588 (6)	0.0527 (6)	0.0641 (7)	0.0081 (5)	0.0285 (5)	0.0063 (5)

N1—C1	1.3209 (16)	C6—H6	0.9300
N1—N2	1.3365 (15)	C7—C8	1.357 (3)
N1—C2	1.4619 (13)	C7—H7	0.9300
N2—N3	1.2978 (17)	C8—C9	1.3854 (18)
N3—N4	1.3449 (19)	C8—H8	0.9300
N4—C1	1.3054 (17)	C9—H9	0.9300
C1—H1	0.9300	C10—C15	1.3783 (17)
C2—C3	1.5301 (15)	C10—C11	1.3918 (16)
C2—H2A	0.9700	C11—C12	1.368 (2)
C2—H2B	0.9700	C11—H11	0.9300
C3—C10	1.5193 (14)	C12—C13	1.362 (3)
C3—C4	1.5212 (15)	C12—H12	0.9300
C3—H3	0.9800	C13—C14	1.377 (2)
C4—C5	1.3818 (18)	C13—H13	0.9300
C4—C9	1.3896 (18)	C14—C15	1.3906 (17)
C5—C6	1.403 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.372 (3)
C1—N1—N2	108.14 (11)	C5—C6—H6	119.7
C1—N1—C2	129.72 (11)	C8—C7—C6	119.97 (15)
N2—N1—C2	122.09 (10)	C8—C7—H7	120.0
N3—N2—N1	106.15 (12)	C6—C7—H7	120.0
N2—N3—N4	110.72 (12)	C7—C8—C9	120.21 (17)
C1—N4—N3	105.44 (11)	C7—C8—H8	119.9
N4—C1—N1	109.55 (13)	C9—C8—H8	119.9
N4—C1—H1	125.2	C8—C9—C4	120.96 (14)
N1—C1—H1	125.2	C8—C9—H9	119.5
N1—C2—C3	112.67 (9)	C4—C9—H9	119.5
N1—C2—H2A	109.1	C15—C10—C11	118.00 (11)
C3—C2—H2A	109.1	C15—C10—C3	123.79 (10)
N1—C2—H2B	109.1	C11—C10—C3	118.18 (11)
C3—C2—H2B	109.1	C12—C11—C10	121.06 (15)
H2A—C2—H2B	107.8	C12—C11—H11	119.5
C10—C3—C4	111.76 (8)	C10—C11—H11	119.5
C10—C3—C2	114.52 (9)	C13—C12—C11	120.68 (14)
C4—C3—C2	107.62 (9)	C13—C12—H12	119.7
C10—C3—H3	107.6	C11—C12—H12	119.7
C4—C3—H3	107.6	C12—C13—C14	119.61 (13)
C2—C3—H3	107.6	C12—C13—H13	120.2
C5—C4—C9	118.66 (12)	C14—C13—H13	120.2
C5—C4—C3	120.54 (12)	C13—C14—C15	120.00 (14)
C9—C4—C3	120.79 (11)	C13—C14—H14	120.0
C4—C5—C6	119.52 (16)	C15—C14—H14	120.0
C4—C5—H5	120.2	C10—C15—C14	120.64 (12)
C6—C5—H5	120.2	C10—C15—H15	119.7
C7—C6—C5	120.67 (16)	C14—C15—H15	119.7
C7—C6—H6	119.7
C1—N1—N2—N3	0.47 (16)	C5—C6—C7—C8	0.4 (3)
C2—N1—N2—N3	178.18 (11)	C6—C7—C8—C9	−0.7 (2)
N1—N2—N3—N4	−0.49 (16)	C7—C8—C9—C4	0.3 (2)
N2—N3—N4—C1	0.32 (17)	C5—C4—C9—C8	0.42 (19)
N3—N4—C1—N1	−0.01 (16)	C3—C4—C9—C8	179.46 (12)
N2—N1—C1—N4	−0.28 (16)	C4—C3—C10—C15	−95.17 (13)
C2—N1—C1—N4	−177.76 (11)	C2—C3—C10—C15	27.54 (15)
C1—N1—C2—C3	−118.85 (13)	C4—C3—C10—C11	82.93 (13)
N2—N1—C2—C3	63.98 (14)	C2—C3—C10—C11	−154.37 (11)
N1—C2—C3—C10	60.68 (12)	C15—C10—C11—C12	1.0 (2)
N1—C2—C3—C4	−174.40 (9)	C3—C10—C11—C12	−177.25 (15)
C10—C3—C4—C5	−116.60 (12)	C10—C11—C12—C13	−0.2 (3)
C2—C3—C4—C5	116.84 (12)	C11—C12—C13—C14	−0.9 (3)
C10—C3—C4—C9	64.38 (13)	C12—C13—C14—C15	1.3 (2)
C2—C3—C4—C9	−62.18 (13)	C11—C10—C15—C14	−0.55 (19)
C9—C4—C5—C6	−0.7 (2)	C3—C10—C15—C14	177.55 (11)
C3—C4—C5—C6	−179.78 (12)	C13—C14—C15—C10	−0.6 (2)
C4—C5—C6—C7	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N3i	0.93	2.61	3.4690 (19)	153
C2—H2B···N4i	0.97	2.50	3.4622 (17)	174
C2—H2A···N4ii	0.97	2.56	3.5155 (17)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N3i	0.93	2.61	3.4690 (19)	153
C2—H2B⋯N4i	0.97	2.50	3.4622 (17)	174
C2—H2A⋯N4ii	0.97	2.56	3.5155 (17)	169

Symmetry codes: (i) ; (ii) .