5,5'-(Butane-1,4-di-yl)bis-(1H-tetra-zole) dihydrate.

The title compound, C(6)H(10)N(8)·2H(2)O, was prepared by the reaction of hexanedinitrile and sodium azide. The di-1H-tetra-zole mol-ecule lies on a crystallographic centre of inversion and is linked to the water mol-ecules by N-H⋯O and O-H⋯N hydrogen bonds, forming a two-dimensional supra-molecular structure in the crystal.

Related literature

For tetra­zole derivatives, see: Demko & Sharpless (2001 ▶); Diop et al. (2002 ▶); Kitagawa et al. (2004 ▶); Li et al. (2007 ▶); Tamura et al. (1998 ▶); Tong et al. (2009 ▶); Zhao et al. (2008 ▶).

Experimental

Crystal data

C6H10N8·2H2O

M = 230.25

Monoclinic,

a = 6.994 (3) Å

b = 11.590 (5) Å

c = 14.097 (6) Å

β = 100.716 (7)°

V = 1122.8 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 294 K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.983

2756 measured reflections

992 independent reflections

722 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.147

S = 1.04

992 reflections

73 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048993/bt5418sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048993/bt5418Isup2.hkl

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

C6H10N8·2H2O	F(000) = 488
Mr = 230.25	Dx = 1.362 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1178 reflections
a = 6.994 (3) Å	θ = 2.9–25.0°
b = 11.590 (5) Å	µ = 0.11 mm−1
c = 14.097 (6) Å	T = 294 K
β = 100.716 (7)°	Block, colorless
V = 1122.8 (8) Å3	0.20 × 0.18 × 0.16 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	992 independent reflections
Radiation source: fine-focus sealed tube	722 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
Tmin = 0.979, Tmax = 0.983	k = −13→10
2756 measured reflections	l = −16→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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0759P)2 + 0.9248P] where P = (Fo2 + 2Fc2)/3
992 reflections	(Δ/σ)max < 0.001
73 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
O1W	0.2175 (3)	0.10913 (15)	0.88483 (13)	0.0697 (7)
H1WA	0.2503	0.0847	0.9424	0.105*
H1WB	0.2153	0.1823	0.8886	0.105*
N1	0.2521 (3)	−0.00531 (16)	0.72515 (14)	0.0487 (6)
H1	0.2430	0.0355	0.7751	0.058*
N2	0.2517 (4)	−0.11987 (17)	0.72219 (16)	0.0607 (7)
N3	0.2679 (4)	−0.14652 (18)	0.63566 (16)	0.0624 (7)
N4	0.2787 (4)	−0.05060 (17)	0.58246 (14)	0.0536 (7)
C1	0.2683 (4)	0.0365 (2)	0.63995 (16)	0.0422 (6)
C3	0.2750 (4)	0.1611 (2)	0.61690 (17)	0.0505 (7)
H3A	0.3991	0.1922	0.6488	0.061*
H3B	0.1737	0.2006	0.6428	0.061*
C4	0.2488 (4)	0.1863 (2)	0.50977 (17)	0.0463 (7)
H4A	0.3525	0.1493	0.4838	0.056*
H4B	0.1261	0.1541	0.4771	0.056*

	U11	U22	U33	U12	U13	U23
O1W	0.131 (2)	0.0449 (11)	0.0368 (11)	0.0010 (11)	0.0256 (11)	−0.0017 (8)
N1	0.0817 (16)	0.0361 (12)	0.0306 (11)	−0.0005 (10)	0.0162 (10)	0.0006 (9)
N2	0.101 (2)	0.0406 (13)	0.0419 (13)	−0.0030 (12)	0.0169 (12)	0.0072 (10)
N3	0.108 (2)	0.0365 (12)	0.0451 (14)	−0.0027 (12)	0.0196 (13)	0.0011 (10)
N4	0.0960 (18)	0.0327 (11)	0.0344 (11)	−0.0022 (11)	0.0181 (11)	0.0010 (9)
C1	0.0603 (16)	0.0364 (12)	0.0306 (12)	−0.0024 (11)	0.0103 (10)	0.0003 (10)
C3	0.082 (2)	0.0344 (13)	0.0373 (14)	−0.0022 (12)	0.0157 (12)	−0.0011 (11)
C4	0.0661 (16)	0.0366 (13)	0.0373 (13)	−0.0007 (12)	0.0120 (11)	0.0020 (10)

O1W—H1WA	0.8500	C1—C3	1.482 (3)
O1W—H1WB	0.8500	C3—C4	1.516 (3)
N1—C1	1.320 (3)	C3—H3A	0.9700
N1—N2	1.328 (3)	C3—H3B	0.9700
N1—H1	0.8600	C4—C4i	1.503 (5)
N2—N3	1.284 (3)	C4—H4A	0.9700
N3—N4	1.351 (3)	C4—H4B	0.9700
N4—C1	1.305 (3)
H1WA—O1W—H1WB	106.1	C1—C3—H3A	108.8
C1—N1—N2	109.8 (2)	C4—C3—H3A	108.8
C1—N1—H1	125.1	C1—C3—H3B	108.8
N2—N1—H1	125.1	C4—C3—H3B	108.8
N3—N2—N1	105.69 (19)	H3A—C3—H3B	107.7
N2—N3—N4	110.7 (2)	C4i—C4—C3	111.7 (3)
C1—N4—N3	106.1 (2)	C4i—C4—H4A	109.3
N4—C1—N1	107.7 (2)	C3—C4—H4A	109.3
N4—C1—C3	127.6 (2)	C4i—C4—H4B	109.3
N1—C1—C3	124.7 (2)	C3—C4—H4B	109.3
C1—C3—C4	113.8 (2)	H4A—C4—H4B	108.0
C1—N1—N2—N3	0.1 (3)	N2—N1—C1—N4	−0.1 (3)
N1—N2—N3—N4	0.0 (3)	N2—N1—C1—C3	−179.6 (2)
N2—N3—N4—C1	0.0 (3)	N4—C1—C3—C4	13.6 (4)
N3—N4—C1—N1	0.1 (3)	N1—C1—C3—C4	−167.1 (3)
N3—N4—C1—C3	179.5 (2)	C1—C3—C4—C4i	178.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···N3ii	0.85	2.02	2.851 (3)	165
O1W—H1WA···N4iii	0.85	1.99	2.822 (3)	167
N1—H1···O1W	0.86	1.80	2.662 (3)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯N3i	0.85	2.02	2.851 (3)	165
O1W—H1WA⋯N4ii	0.85	1.99	2.822 (3)	167
N1—H1⋯O1W	0.86	1.80	2.662 (3)	175

Symmetry codes: (i) ; (ii) .