Crystal structure of 1-(5-amino-2H-tetra-zol-2-yl)-2-methyl-propan-2-ol.

The title compound, C5H11N5O, crystallized with two independent mol-ecules in the asymmetric unit. The two mol-ecules differ in the orientation of the 2-methyl-propan-2-ol unit, with the hy-droxy H atoms pointing in opposite directions. In the crystal, mol-ecules 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.

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 ▸).

Experimental

Crystal data

C5H11N5O

M = 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

Δρmax = 0.17 e Å−3

Δρmin = −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.

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

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

Click here for additional data file.

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

Click here for additional data file.

. 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.

. 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.

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

C5H11N5O	Z = 4
Mr = 157.19	F(000) = 336
Triclinic, P1	Dx = 1.305 Mg m−3
a = 8.2472 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.731 (2) Å	Cell parameters from 4382 reflections
c = 10.087 (2) Å	θ = 2.0–29.9°
α = 90.30 (1)°	µ = 0.10 mm−1
β = 96.228 (10)°	T = 296 K
γ = 96.259 (10)°	Block, colourless
V = 799.8 (3) Å3	0.12 × 0.10 × 0.08 mm

Bruker SMART 1K CCD diffractometer	2953 independent reflections
Radiation source: fine-focus sealed tube	2148 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
profile data from ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −9→9
Tmin = 0.90, Tmax = 0.95	k = −11→11
11190 measured reflections	l = −12→12

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.018P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2953 reflections	Δρmax = 0.17 e Å−3
227 parameters	Δρmin = −0.19 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.

	x	y	z	Uiso*/Ueq
O1	0.28249 (16)	0.86314 (15)	0.81161 (14)	0.0536 (4)
H1O	0.270 (3)	0.952 (3)	0.789 (3)	0.101 (9)*
N1	0.4219 (2)	0.6570 (2)	1.28100 (17)	0.0530 (5)
H1A	0.527 (3)	0.690 (2)	1.315 (2)	0.063 (7)*
H1B	0.378 (2)	0.592 (2)	1.3251 (19)	0.048 (6)*
N2	0.48661 (17)	0.69286 (15)	1.05833 (15)	0.0405 (4)
N3	0.40258 (18)	0.64638 (14)	0.94250 (14)	0.0383 (4)
N4	0.26829 (19)	0.56520 (15)	0.95690 (15)	0.0463 (4)
N5	0.25930 (18)	0.55592 (16)	1.08764 (15)	0.0458 (4)
C1	0.3924 (2)	0.63485 (18)	1.14668 (18)	0.0376 (4)
C2	0.4501 (2)	0.68157 (18)	0.80986 (18)	0.0456 (5)
H2A	0.3810	0.6223	0.7440	0.055*
H2B	0.5624	0.6622	0.8062	0.055*
C3	0.4370 (2)	0.83230 (18)	0.77215 (18)	0.0432 (5)
C4	0.5765 (2)	0.9290 (2)	0.8434 (2)	0.0572 (6)
H4A	0.5651	1.0223	0.8165	0.086*
H4B	0.6794	0.9034	0.8208	0.086*
H4C	0.5732	0.9226	0.9380	0.086*
C5	0.4359 (3)	0.8413 (2)	0.6213 (2)	0.0730 (7)
H5A	0.3447	0.7815	0.5786	0.110*
H5B	0.5363	0.8133	0.5957	0.110*
H5C	0.4260	0.9348	0.5945	0.110*
O2	0.24050 (17)	0.15721 (15)	0.77069 (15)	0.0509 (4)
H2O	0.301 (4)	0.198 (3)	0.831 (3)	0.131 (13)*
N6	0.0533 (3)	0.3192 (2)	0.24056 (16)	0.0523 (5)
H6A	−0.054 (3)	0.283 (2)	0.214 (2)	0.065 (7)*
H6B	0.093 (2)	0.377 (2)	0.191 (2)	0.057 (7)*
N7	0.00343 (18)	0.29922 (16)	0.46818 (14)	0.0436 (4)
N8	0.09725 (18)	0.34753 (14)	0.57877 (14)	0.0382 (4)
N9	0.23381 (19)	0.42091 (16)	0.55631 (15)	0.0505 (4)
N10	0.23478 (19)	0.42088 (17)	0.42439 (15)	0.0516 (5)
C6	0.0940 (2)	0.34662 (18)	0.37369 (17)	0.0377 (4)
C7	0.0495 (2)	0.32626 (18)	0.71339 (17)	0.0416 (5)
H7A	−0.0649	0.3416	0.7126	0.050*
H7B	0.1138	0.3952	0.7729	0.050*
C8	0.0714 (2)	0.18313 (18)	0.76967 (17)	0.0386 (4)
C9	0.0260 (3)	0.1839 (2)	0.9121 (2)	0.0652 (7)
H9A	0.0504	0.0992	0.9542	0.098*
H9B	−0.0891	0.1923	0.9108	0.098*
H9C	0.0881	0.2607	0.9610	0.098*
C10	−0.0294 (3)	0.0686 (2)	0.6850 (2)	0.0573 (6)
H10A	0.0133	0.0630	0.6005	0.086*
H10B	−0.1416	0.0880	0.6710	0.086*
H10C	−0.0237	−0.0178	0.7298	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0434 (8)	0.0474 (9)	0.0716 (10)	0.0081 (7)	0.0097 (7)	0.0127 (7)
N1	0.0503 (12)	0.0632 (12)	0.0421 (11)	−0.0055 (10)	0.0018 (9)	0.0068 (9)
N2	0.0397 (9)	0.0411 (9)	0.0389 (9)	0.0004 (7)	0.0010 (7)	0.0029 (7)
N3	0.0432 (9)	0.0329 (8)	0.0379 (9)	0.0030 (7)	0.0023 (7)	0.0032 (7)
N4	0.0500 (10)	0.0425 (9)	0.0436 (10)	−0.0031 (8)	0.0008 (7)	0.0055 (7)
N5	0.0436 (10)	0.0482 (10)	0.0436 (10)	−0.0011 (8)	0.0021 (7)	0.0076 (7)
C1	0.0356 (10)	0.0374 (10)	0.0395 (11)	0.0052 (8)	0.0015 (8)	0.0049 (8)
C2	0.0558 (12)	0.0436 (11)	0.0389 (11)	0.0073 (9)	0.0095 (9)	0.0002 (9)
C3	0.0446 (11)	0.0401 (11)	0.0454 (11)	0.0035 (9)	0.0083 (9)	0.0069 (9)
C4	0.0513 (13)	0.0492 (13)	0.0705 (15)	−0.0013 (10)	0.0098 (11)	0.0077 (11)
C5	0.0948 (19)	0.0761 (17)	0.0485 (13)	0.0069 (14)	0.0111 (13)	0.0190 (12)
O2	0.0433 (8)	0.0501 (9)	0.0586 (10)	0.0054 (7)	0.0015 (7)	0.0067 (7)
N6	0.0598 (12)	0.0577 (12)	0.0362 (10)	−0.0039 (10)	0.0007 (9)	0.0061 (8)
N7	0.0432 (9)	0.0492 (10)	0.0355 (9)	−0.0032 (7)	−0.0013 (7)	0.0030 (7)
N8	0.0410 (9)	0.0374 (9)	0.0347 (9)	0.0003 (7)	0.0010 (7)	0.0052 (7)
N9	0.0506 (10)	0.0563 (11)	0.0403 (10)	−0.0081 (8)	−0.0015 (8)	0.0093 (8)
N10	0.0489 (10)	0.0637 (11)	0.0390 (9)	−0.0062 (8)	0.0027 (8)	0.0102 (8)
C6	0.0413 (11)	0.0361 (10)	0.0357 (10)	0.0051 (8)	0.0030 (8)	0.0059 (8)
C7	0.0529 (12)	0.0379 (11)	0.0348 (10)	0.0059 (9)	0.0078 (9)	0.0018 (8)
C8	0.0396 (11)	0.0383 (11)	0.0380 (10)	0.0031 (8)	0.0056 (8)	0.0049 (8)
C9	0.0835 (17)	0.0633 (15)	0.0513 (13)	0.0076 (12)	0.0191 (12)	0.0159 (11)
C10	0.0582 (14)	0.0447 (12)	0.0648 (14)	−0.0055 (10)	−0.0005 (11)	0.0037 (10)

O1—C3	1.437 (2)	O2—C8	1.443 (2)
O1—H1O	0.91 (3)	O2—H2O	0.82 (3)
N1—C1	1.362 (2)	N6—C6	1.366 (2)
N1—H1A	0.92 (2)	N6—H6A	0.93 (2)
N1—H1B	0.844 (19)	N6—H6B	0.82 (2)
N2—C1	1.333 (2)	N7—C6	1.328 (2)
N2—N3	1.342 (2)	N7—N8	1.339 (2)
N3—N4	1.310 (2)	N8—N9	1.308 (2)
N3—C2	1.466 (2)	N8—C7	1.464 (2)
N4—N5	1.332 (2)	N9—N10	1.332 (2)
N5—C1	1.349 (2)	N10—C6	1.347 (2)
C2—C3	1.529 (3)	C7—C8	1.528 (2)
C2—H2A	0.9700	C7—H7A	0.9700
C2—H2B	0.9700	C7—H7B	0.9700
C3—C4	1.518 (3)	C8—C10	1.515 (3)
C3—C5	1.524 (3)	C8—C9	1.524 (2)
C4—H4A	0.9600	C9—H9A	0.9600
C4—H4B	0.9600	C9—H9B	0.9600
C4—H4C	0.9600	C9—H9C	0.9600
C5—H5A	0.9600	C10—H10A	0.9600
C5—H5B	0.9600	C10—H10B	0.9600
C5—H5C	0.9600	C10—H10C	0.9600
C3—O1—H1O	107.4 (15)	C8—O2—H2O	113 (2)
C1—N1—H1A	117.3 (13)	C6—N6—H6A	116.9 (13)
C1—N1—H1B	113.0 (14)	C6—N6—H6B	114.9 (15)
H1A—N1—H1B	114.2 (18)	H6A—N6—H6B	115.5 (19)
C1—N2—N3	101.66 (14)	C6—N7—N8	101.56 (14)
N4—N3—N2	113.70 (14)	N9—N8—N7	114.12 (14)
N4—N3—C2	121.24 (15)	N9—N8—C7	122.32 (15)
N2—N3—C2	125.06 (14)	N7—N8—C7	123.51 (14)
N3—N4—N5	106.41 (14)	N8—N9—N10	105.90 (15)
N4—N5—C1	105.97 (13)	N9—N10—C6	106.18 (14)
N2—C1—N5	112.25 (16)	N7—C6—N10	112.23 (16)
N2—C1—N1	124.33 (17)	N7—C6—N6	124.23 (18)
N5—C1—N1	123.35 (16)	N10—C6—N6	123.49 (16)
N3—C2—C3	114.27 (14)	N8—C7—C8	114.86 (14)
N3—C2—H2A	108.7	N8—C7—H7A	108.6
C3—C2—H2A	108.7	C8—C7—H7A	108.6
N3—C2—H2B	108.7	N8—C7—H7B	108.6
C3—C2—H2B	108.7	C8—C7—H7B	108.6
H2A—C2—H2B	107.6	H7A—C7—H7B	107.5
O1—C3—C4	110.33 (16)	O2—C8—C10	106.22 (15)
O1—C3—C5	110.39 (16)	O2—C8—C9	109.55 (15)
C4—C3—C5	111.14 (16)	C10—C8—C9	112.03 (15)
O1—C3—C2	105.38 (14)	O2—C8—C7	109.61 (13)
C4—C3—C2	111.81 (16)	C10—C8—C7	112.28 (15)
C5—C3—C2	107.60 (16)	C9—C8—C7	107.14 (15)
C3—C4—H4A	109.5	C8—C9—H9A	109.5
C3—C4—H4B	109.5	C8—C9—H9B	109.5
H4A—C4—H4B	109.5	H9A—C9—H9B	109.5
C3—C4—H4C	109.5	C8—C9—H9C	109.5
H4A—C4—H4C	109.5	H9A—C9—H9C	109.5
H4B—C4—H4C	109.5	H9B—C9—H9C	109.5
C3—C5—H5A	109.5	C8—C10—H10A	109.5
C3—C5—H5B	109.5	C8—C10—H10B	109.5
H5A—C5—H5B	109.5	H10A—C10—H10B	109.5
C3—C5—H5C	109.5	C8—C10—H10C	109.5
H5A—C5—H5C	109.5	H10A—C10—H10C	109.5
H5B—C5—H5C	109.5	H10B—C10—H10C	109.5
C1—N2—N3—N4	−0.60 (19)	C6—N7—N8—N9	1.0 (2)
C1—N2—N3—C2	178.59 (15)	C6—N7—N8—C7	178.36 (15)
N2—N3—N4—N5	0.2 (2)	N7—N8—N9—N10	−1.1 (2)
C2—N3—N4—N5	−178.98 (14)	C7—N8—N9—N10	−178.47 (14)
N3—N4—N5—C1	0.23 (19)	N8—N9—N10—C6	0.6 (2)
N3—N2—C1—N5	0.74 (19)	N8—N7—C6—N10	−0.5 (2)
N3—N2—C1—N1	−176.40 (17)	N8—N7—C6—N6	177.00 (17)
N4—N5—C1—N2	−0.6 (2)	N9—N10—C6—N7	−0.1 (2)
N4—N5—C1—N1	176.53 (17)	N9—N10—C6—N6	−177.61 (17)
N4—N3—C2—C3	110.47 (19)	N9—N8—C7—C8	−104.44 (19)
N2—N3—C2—C3	−68.7 (2)	N7—N8—C7—C8	78.4 (2)
N3—C2—C3—O1	−44.3 (2)	N8—C7—C8—O2	57.7 (2)
N3—C2—C3—C4	75.5 (2)	N8—C7—C8—C10	−60.1 (2)
N3—C2—C3—C5	−162.14 (16)	N8—C7—C8—C9	176.52 (15)

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···O1iv	0.93 (2)	2.22 (2)	3.114 (3)	161 (2)
N6—H6B···N5v	0.82 (2)	2.41 (2)	3.213 (2)	167 (2)

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⋯O1iv	0.93 (2)	2.22 (2)	3.114 (3)	161 (2)
N6—H6B⋯N5v	0.82 (2)	2.41 (2)	3.213 (2)	167 (2)

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