Crystal structure of 1-(5-amino-2H-tetra­zol-2-yl)-2-methyl­propan-2-ol

Hyun Sik Park; Ji Yeon Ryu; Junseong Lee

doi:10.1107/S2056989015023713

. 2015 Dec 16;71(Pt 12):o1057–o1058. doi: 10.1107/S2056989015023713

Crystal structure of 1-(5-amino-2H-tetrazol-2-yl)-2-methylpropan-2-ol

Hyun Sik Park ^a, Ji Yeon Ryu ^a, Junseong Lee ^a,^*

PMCID: PMC4719977 PMID: 26870496

Abstract

The title compound, C₅H₁₁N₅O, crystallized with two independent molecules in the asymmetric unit. The two molecules differ in the orientation of the 2-methylpropan-2-ol unit, with the hydroxy H atoms pointing in opposite directions. In the crystal, molecules are linked via O—H⋯O and N—H⋯O hydrogen bonds, forming ribbons propagating along [10-1]. The ribbons are linked via N—H⋯N hydrogen bonds, forming a three-dimensional structure.

Keywords: crystal structure, 5-aminotetrazole, 2-methylpropan-2-ol, hydrogen bonding

Related literature

For the crystal structure of 5-aminotetrazole monohydrate, see: Britts & Karle (1967 ▸); and for that of 5-aminotetrazole, see: Fujihisa et al. (2011 ▸). For the crystal structures of alkali salts of 5-aminotetrazole, see: Ernst et al. (2007 ▸). For the crystal structure of 5-azido-1H-tetrazole, a highly explosive compound, see: Stierstorfer et al. (2008 ▸). For some examples of the use of 5-aminotetrazole in the synthesis of metal–organic frameworks, see: Karaghiosoff et al. (2009 ▸); Liu et al. (2013 ▸). graphic file with name e-71-o1057-scheme1.jpg

Experimental

Crystal data

C₅H₁₁N₅O
M _r = 157.19
Triclinic,
a = 8.2472 (19) Å
b = 9.731 (2) Å
c = 10.087 (2) Å
α = 90.30 (1)°
β = 96.228 (10)°
γ = 96.259 (10)°
V = 799.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ▸) T _min = 0.90, T _max = 0.95
11190 measured reflections
2953 independent reflections
2148 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.122
S = 1.06
2953 reflections
227 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▸); cell refinement: SAINT (Bruker, 2006 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL2014 and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015023713/su5257sup1.cif

e-71-o1057-sup1.cif^{(401.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015023713/su5257Isup2.hkl

e-71-o1057-Isup2.hkl^{(236KB, hkl)}

Click here for additional data file.^{(3.6KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015023713/su5257Isup3.cml

Click here for additional data file.^{(1.7MB, tif)}

. DOI: 10.1107/S2056989015023713/su5257fig1.tif

The molecular structure of the two independent molecules (A and B) of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989015023713/su5257fig2.tif

A view of the molecular overlap of molecules A (black) and B (red); calculated using the AutoMolfit routine in PLATON (Spek, 2009).

Click here for additional data file.^{(2.7MB, tif)}

c . DOI: 10.1107/S2056989015023713/su5257fig3.tif

A view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1). H atoms not involved in hydrogen bonding have been omitted for clarity.

CCDC reference: 1441577

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2ⁱ	0.91 (3)	2.04 (3)	2.946 (2)	171 (2)
N1—H1A⋯O2ⁱⁱ	0.92 (2)	2.53 (2)	3.243 (2)	135 (2)
N1—H1A⋯N9ⁱⁱ	0.92 (2)	2.58 (2)	3.287 (3)	134 (2)
N1—H1B⋯N10ⁱⁱⁱ	0.84 (2)	2.24 (2)	3.082 (2)	173 (2)
O2—H2O⋯N2ⁱⁱ	0.82 (3)	2.14 (3)	2.930 (2)	162 (3)
N6—H6A⋯O1^iv	0.93 (2)	2.22 (2)	3.114 (3)	161 (2)
N6—H6B⋯N5^v	0.82 (2)	2.41 (2)	3.213 (2)	167 (2)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

This work was supported by a Chonnam National University research grant in 2014.

supplementary crystallographic information

S1. Comments

Tetrazole compounds are useful building blocks for the construction of high dimensional metal-organic frameworks, and they have provided various binding modes toward metal centers (Karaghiosoff et al., 2009; Liu et al., 2013). The title compound was easily prepared by the reaction of 5-aminotetrazole and iso-butylene oxide, and introduces an hydroxyl group which we hope will be useful as an additional coordination center.

The title compound, Fig. 1, crystallized with two independent molecules(A and B) in the asymmetric unit. The two molecules differ in the orientation of the 2-methylpropan-2-ol unit, with the hydroxyl H atoms pointing in opposite directions (Fig. 2).

In the crystal, molecules are linked via O—H···O and N—H···O hydrogen bonds (Table 1) forming ribbons propagating along direction [101]. The ribbons are linked via N—H···N hydrogen bonds forming a three-dimensional structure (Table 1 and Fig. 3).

S2. Synthesis and crystallization

The title compound was synthesized by heating 5-aminotetrazole with an excess amount of iso-butylene oxide, without solvent, at 333 K. Crystals were obtained on cooling the reaction mixture.

S3. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The OH and NH₂ H atoms were located in difference Fourier maps and freely refined. The C-bound H atoms were positioned geometrically and refined using a riding model: C—H = 0.96–0.97 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.