5-Pentyl-1H-tetra-zole.

The title compound C(6)H(12)N(4), is one of a few known tetra-zoles with an alkyl chain in the 5-position. The asymmetric unit contains two independent mol-ecules. The mol-ecules are linked by N-H⋯N inter-actions into chains with graph-set notation D(2) and C(2) (2)(8) along [010]. The two independent mol-ecules form a layered structure, the layers being composed of inter-digitating strands of alternatingly oriented and nearly identical mol-ecules.

Related literature

For synthetic methods see: Mihina & Herbst (1950 ▶); Steven et al. (1993 ▶); Detert & Schollmeyer (1999 ▶); Sugiono & Detert (2001 ▶); Glang et al. (2008 ▶); Borchmann et al. (2010 ▶). For the properties of tetra­zole, see: Huisgen et al. (1960a ▶,b ▶, 1961 ▶); Singh (1980 ▶); Pernice et al. (1988 ▶); Huff et al. (1996 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C6H12N4

M = 140.20

Triclinic,

a = 8.7812 (14) Å

b = 9.6770 (12) Å

c = 11.614 (2) Å

α = 93.136 (10)°

β = 112.059 (9)°

γ = 116.389 (7)°

V = 789.6 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.63 mm−1

T = 193 K

0.50 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

3182 measured reflections

2991 independent reflections

2764 reflections with I > 2σ(I)

R int = 0.070

3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.109

S = 1.04

2991 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052244/bx2337sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052244/bx2337Isup2.hkl

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

C6H12N4	Z = 4
Mr = 140.20	F(000) = 304
Triclinic, P1	Dx = 1.179 Mg m−3
Hall symbol: -P 1	Melting point: 315 K
a = 8.7812 (14) Å	Cu Kα radiation, λ = 1.54178 Å
b = 9.6770 (12) Å	Cell parameters from 25 reflections
c = 11.614 (2) Å	θ = 65–69°
α = 93.136 (10)°	µ = 0.63 mm−1
β = 112.059 (9)°	T = 193 K
γ = 116.389 (7)°	Block, colourless
V = 789.6 (2) Å3	0.50 × 0.40 × 0.30 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.070
Radiation source: rotating anode	θmax = 70.0°, θmin = 4.3°
graphite	h = −10→9
ω/2θ scans	k = 0→11
3182 measured reflections	l = −14→14
2991 independent reflections	3 standard reflections every 60 min
2764 reflections with I > 2σ(I)	intensity decay: 2%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0611P)2 + 0.1618P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2991 reflections	Δρmax = 0.24 e Å−3
184 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0088 (12)

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
N1A	0.76292 (14)	0.44445 (11)	0.33040 (10)	0.0321 (2)
H1A	0.7628	0.5432	0.3397	0.038*
N2A	0.77322 (17)	0.38035 (13)	0.22933 (10)	0.0392 (3)
N3A	0.77338 (17)	0.25012 (13)	0.24908 (11)	0.0413 (3)
N4A	0.76329 (16)	0.22891 (12)	0.36157 (10)	0.0358 (3)
C5A	0.75588 (16)	0.35102 (13)	0.41070 (11)	0.0286 (3)
C6A	0.74035 (18)	0.38071 (13)	0.53191 (11)	0.0321 (3)
H6A	0.6195	0.3797	0.5105	0.039*
H6B	0.8458	0.4884	0.5875	0.039*
C7A	0.74667 (18)	0.25697 (14)	0.60683 (12)	0.0336 (3)
H7A	0.6359	0.1501	0.5540	0.040*
H7B	0.8633	0.2525	0.6233	0.040*
C8A	0.74449 (18)	0.29643 (15)	0.73469 (12)	0.0360 (3)
H8A	0.6351	0.3123	0.7186	0.043*
H8B	0.8619	0.3983	0.7905	0.043*
C9A	0.7308 (2)	0.16675 (18)	0.80548 (14)	0.0441 (3)
H9A	0.6116	0.0655	0.7507	0.053*
H9B	0.8383	0.1489	0.8197	0.053*
C10A	0.7338 (3)	0.2091 (2)	0.93461 (16)	0.0607 (4)
H10A	0.7183	0.1198	0.9740	0.091*
H10B	0.6298	0.2299	0.9215	0.091*
H10C	0.8555	0.3050	0.9916	0.091*
N1B	0.77122 (14)	0.95284 (11)	0.40731 (9)	0.0305 (2)
H1B	0.7639	1.0469	0.3995	0.037*
N2B	0.74619 (15)	0.88499 (12)	0.50153 (10)	0.0350 (3)
N3B	0.74529 (16)	0.75189 (12)	0.47932 (10)	0.0364 (3)
N4B	0.76875 (15)	0.73261 (12)	0.37130 (10)	0.0336 (2)
C5B	0.78464 (16)	0.85919 (13)	0.32751 (11)	0.0288 (3)
C6B	0.81748 (19)	0.89627 (13)	0.21354 (12)	0.0359 (3)
H6C	0.9558	0.9640	0.2423	0.043*
H6D	0.7569	0.9590	0.1766	0.043*
C7B	0.74053 (18)	0.74860 (13)	0.10847 (11)	0.0326 (3)
H7C	0.8051	0.6880	0.1436	0.039*
H7D	0.6030	0.6784	0.0813	0.039*
C8B	0.77032 (18)	0.79245 (14)	−0.00809 (11)	0.0341 (3)
H8C	0.7002	0.8484	−0.0453	0.041*
H8D	0.9071	0.8678	0.0205	0.041*
C9B	0.70495 (19)	0.64908 (15)	−0.11205 (12)	0.0380 (3)
H9C	0.5680	0.5737	−0.1411	0.046*
H9D	0.7749	0.5930	−0.0751	0.046*
C10B	0.7361 (2)	0.69521 (18)	−0.22777 (13)	0.0501 (4)
H10D	0.6736	0.5983	−0.2974	0.075*
H10E	0.8727	0.7536	−0.2030	0.075*
H10F	0.6822	0.7635	−0.2575	0.075*

	U11	U22	U33	U12	U13	U23
N1A	0.0489 (6)	0.0245 (5)	0.0357 (5)	0.0239 (4)	0.0240 (5)	0.0118 (4)
N2A	0.0627 (7)	0.0336 (6)	0.0384 (6)	0.0314 (5)	0.0295 (5)	0.0145 (4)
N3A	0.0686 (7)	0.0333 (6)	0.0397 (6)	0.0336 (5)	0.0308 (6)	0.0135 (5)
N4A	0.0564 (6)	0.0268 (5)	0.0379 (6)	0.0269 (5)	0.0264 (5)	0.0118 (4)
C5A	0.0357 (6)	0.0209 (5)	0.0337 (6)	0.0163 (5)	0.0171 (5)	0.0077 (4)
C6A	0.0446 (6)	0.0263 (6)	0.0350 (6)	0.0218 (5)	0.0219 (5)	0.0094 (5)
C7A	0.0440 (7)	0.0288 (6)	0.0360 (6)	0.0214 (5)	0.0214 (5)	0.0112 (5)
C8A	0.0426 (7)	0.0348 (6)	0.0348 (6)	0.0211 (5)	0.0193 (5)	0.0100 (5)
C9A	0.0566 (8)	0.0519 (8)	0.0428 (7)	0.0358 (7)	0.0283 (6)	0.0228 (6)
C10A	0.0868 (12)	0.0807 (12)	0.0495 (9)	0.0573 (10)	0.0426 (9)	0.0353 (8)
N1B	0.0454 (6)	0.0229 (5)	0.0326 (5)	0.0217 (4)	0.0203 (4)	0.0098 (4)
N2B	0.0511 (6)	0.0294 (5)	0.0353 (5)	0.0242 (5)	0.0242 (5)	0.0116 (4)
N3B	0.0544 (6)	0.0303 (5)	0.0370 (5)	0.0255 (5)	0.0263 (5)	0.0151 (4)
N4B	0.0520 (6)	0.0262 (5)	0.0362 (5)	0.0250 (5)	0.0256 (5)	0.0133 (4)
C5B	0.0386 (6)	0.0206 (5)	0.0312 (6)	0.0168 (5)	0.0169 (5)	0.0074 (4)
C6B	0.0554 (7)	0.0235 (6)	0.0359 (6)	0.0205 (5)	0.0260 (6)	0.0118 (5)
C7B	0.0440 (7)	0.0240 (6)	0.0350 (6)	0.0174 (5)	0.0220 (5)	0.0094 (5)
C8B	0.0457 (7)	0.0276 (6)	0.0339 (6)	0.0194 (5)	0.0206 (5)	0.0117 (5)
C9B	0.0507 (7)	0.0322 (6)	0.0347 (6)	0.0208 (6)	0.0224 (6)	0.0097 (5)
C10B	0.0734 (10)	0.0466 (8)	0.0388 (7)	0.0305 (7)	0.0324 (7)	0.0150 (6)

N1A—C5A	1.3330 (15)	N1B—C5B	1.3339 (15)
N1A—N2A	1.3494 (14)	N1B—N2B	1.3446 (14)
N1A—H1A	0.9564	N1B—H1B	0.9474
N2A—N3A	1.2937 (14)	N2B—N3B	1.2956 (14)
N3A—N4A	1.3628 (15)	N3B—N4B	1.3616 (14)
N4A—C5A	1.3223 (14)	N4B—C5B	1.3222 (14)
C5A—C6A	1.4892 (16)	C5B—C6B	1.4868 (16)
C6A—C7A	1.5267 (16)	C6B—C7B	1.5228 (16)
C6A—H6A	0.9900	C6B—H6C	0.9900
C6A—H6B	0.9900	C6B—H6D	0.9900
C7A—C8A	1.5222 (16)	C7B—C8B	1.5203 (16)
C7A—H7A	0.9900	C7B—H7C	0.9900
C7A—H7B	0.9900	C7B—H7D	0.9900
C8A—C9A	1.5226 (18)	C8B—C9B	1.5167 (17)
C8A—H8A	0.9900	C8B—H8C	0.9900
C8A—H8B	0.9900	C8B—H8D	0.9900
C9A—C10A	1.520 (2)	C9B—C10B	1.5212 (17)
C9A—H9A	0.9900	C9B—H9C	0.9900
C9A—H9B	0.9900	C9B—H9D	0.9900
C10A—H10A	0.9800	C10B—H10D	0.9800
C10A—H10B	0.9800	C10B—H10E	0.9800
C10A—H10C	0.9800	C10B—H10F	0.9800
C5A—N1A—N2A	109.67 (9)	C5B—N1B—N2B	109.65 (9)
C5A—N1A—H1A	127.6	C5B—N1B—H1B	129.2
N2A—N1A—H1A	122.7	N2B—N1B—H1B	120.8
N3A—N2A—N1A	106.07 (10)	N3B—N2B—N1B	106.22 (9)
N2A—N3A—N4A	110.18 (10)	N2B—N3B—N4B	110.06 (9)
C5A—N4A—N3A	106.84 (9)	C5B—N4B—N3B	106.84 (9)
N4A—C5A—N1A	107.23 (10)	N4B—C5B—N1B	107.23 (10)
N4A—C5A—C6A	127.37 (10)	N4B—C5B—C6B	127.50 (10)
N1A—C5A—C6A	125.40 (10)	N1B—C5B—C6B	125.25 (10)
C5A—C6A—C7A	112.98 (9)	C5B—C6B—C7B	113.84 (9)
C5A—C6A—H6A	109.0	C5B—C6B—H6C	108.8
C7A—C6A—H6A	109.0	C7B—C6B—H6C	108.8
C5A—C6A—H6B	109.0	C5B—C6B—H6D	108.8
C7A—C6A—H6B	109.0	C7B—C6B—H6D	108.8
H6A—C6A—H6B	107.8	H6C—C6B—H6D	107.7
C8A—C7A—C6A	111.95 (10)	C8B—C7B—C6B	111.84 (10)
C8A—C7A—H7A	109.2	C8B—C7B—H7C	109.2
C6A—C7A—H7A	109.2	C6B—C7B—H7C	109.2
C8A—C7A—H7B	109.2	C8B—C7B—H7D	109.2
C6A—C7A—H7B	109.2	C6B—C7B—H7D	109.2
H7A—C7A—H7B	107.9	H7C—C7B—H7D	107.9
C7A—C8A—C9A	113.17 (11)	C9B—C8B—C7B	113.44 (10)
C7A—C8A—H8A	108.9	C9B—C8B—H8C	108.9
C9A—C8A—H8A	108.9	C7B—C8B—H8C	108.9
C7A—C8A—H8B	108.9	C9B—C8B—H8D	108.9
C9A—C8A—H8B	108.9	C7B—C8B—H8D	108.9
H8A—C8A—H8B	107.8	H8C—C8B—H8D	107.7
C10A—C9A—C8A	112.79 (12)	C8B—C9B—C10B	112.71 (11)
C10A—C9A—H9A	109.0	C8B—C9B—H9C	109.0
C8A—C9A—H9A	109.0	C10B—C9B—H9C	109.0
C10A—C9A—H9B	109.0	C8B—C9B—H9D	109.0
C8A—C9A—H9B	109.0	C10B—C9B—H9D	109.0
H9A—C9A—H9B	107.8	H9C—C9B—H9D	107.8
C9A—C10A—H10A	109.5	C9B—C10B—H10D	109.5
C9A—C10A—H10B	109.5	C9B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C9A—C10A—H10C	109.5	C9B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C5A—N1A—N2A—N3A	−0.33 (14)	C5B—N1B—N2B—N3B	0.27 (13)
N1A—N2A—N3A—N4A	0.02 (14)	N1B—N2B—N3B—N4B	−0.24 (13)
N2A—N3A—N4A—C5A	0.30 (15)	N2B—N3B—N4B—C5B	0.13 (14)
N3A—N4A—C5A—N1A	−0.49 (13)	N3B—N4B—C5B—N1B	0.04 (13)
N3A—N4A—C5A—C6A	178.87 (11)	N3B—N4B—C5B—C6B	178.27 (11)
N2A—N1A—C5A—N4A	0.52 (14)	N2B—N1B—C5B—N4B	−0.19 (13)
N2A—N1A—C5A—C6A	−178.86 (11)	N2B—N1B—C5B—C6B	−178.47 (11)
N4A—C5A—C6A—C7A	3.98 (18)	N4B—C5B—C6B—C7B	28.32 (18)
N1A—C5A—C6A—C7A	−176.77 (11)	N1B—C5B—C6B—C7B	−153.76 (12)
C5A—C6A—C7A—C8A	176.01 (10)	C5B—C6B—C7B—C8B	177.66 (10)
C6A—C7A—C8A—C9A	174.26 (11)	C6B—C7B—C8B—C9B	176.94 (11)
C7A—C8A—C9A—C10A	178.51 (12)	C7B—C8B—C9B—C10B	−179.91 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N4B	0.96	1.82	2.7773 (14)	175
N1B—H1B···N4Ai	0.95	1.84	2.7779 (14)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯N4B	0.96	1.82	2.7773 (14)	175
N1B—H1B⋯N4Ai	0.95	1.84	2.7779 (14)	170

Symmetry code: (i) .