1-[2-(Di-methyl-aza-nium-yl)eth-yl]-1H-1,2,3,4-tetra-zole-5-thiol-ate.

In the crystal structure of the title zwitterion, C5H11N5S, mol-ecules are linked via N-H⋯N hydrogen bonds, forming zigzag chains propagating along [010]. The chains are linked by C-H⋯S hydrogen bonds, forming two dimensional networks lying parallel to (001).

Related literature

For the biological activity of tetra­zoles, see: Juby et al. (1982 ▶); Tamilselvi & Mugesh (2009 ▶, 2011 ▶). For the general existence of zwitterions in other mol­ecules and the involvement of a protonated N atom in hydrogen bonding, see: Ruanwas et al. (2012 ▶); Ha (2012 ▶). For the biological activity of cefotiam (systematic name: (6R,7R)-7-{[2-(2-amino-1,3-thia­zol-4-yl)acet­yl]amino}-3-{[1-(2-di­methyl­amino­eth­yl)tetra­zol-5-yl), an anti­obiotic with DMETT [1-(2-(di­methyl­amino)-eth­yl)-1H-tetra­zole-5-thione] as a side chain, against enterobacteriacea, see: Garcia-Rodriguez et al. (1995 ▶); Polis & Tuazon (1985 ▶).

Experimental

Crystal data

C5H11N5S

M = 173.26

Monoclinic,

a = 7.1021 (1) Å

b = 11.2476 (2) Å

c = 10.7045 (2) Å

β = 102.479 (1)°

V = 834.89 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 100 K

0.41 × 0.21 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.876, T max = 0.955

11518 measured reflections

3004 independent reflections

2618 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.092

S = 1.05

3004 reflections

106 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2008 ▶) and POV-RAY (Cason, 2004 ▶); software used to prepare material for publication: PLATON and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814001573/bv2228sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001573/bv2228Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001573/bv2228Isup3.cml

CCDC reference:

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

C5H11N5S	F(000) = 368
Mr = 173.26	Dx = 1.378 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3004 reflections
a = 7.1021 (1) Å	θ = 2.7–32.7°
b = 11.2476 (2) Å	µ = 0.33 mm−1
c = 10.7045 (2) Å	T = 100 K
β = 102.479 (1)°	Prism, colourless
V = 834.89 (2) Å3	0.41 × 0.21 × 0.14 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3004 independent reflections
Radiation source: fine-focus sealed tube	2618 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scan	θmax = 32.7°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
Tmin = 0.876, Tmax = 0.955	k = −16→16
11518 measured reflections	l = −16→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0391P)2 + 0.4372P] where P = (Fo2 + 2Fc2)/3
3004 reflections	(Δ/σ)max = 0.002
106 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S1	1.21899 (4)	1.07521 (3)	0.25401 (3)	0.0158 (1)
N1	0.85227 (13)	1.05977 (8)	0.10942 (9)	0.0111 (2)
N2	0.71652 (14)	1.12926 (9)	0.03430 (9)	0.0146 (3)
N3	0.79116 (14)	1.23401 (9)	0.03491 (10)	0.0155 (3)
N4	0.97380 (13)	1.23578 (9)	0.10896 (9)	0.0129 (2)
N5	0.72606 (14)	0.90248 (8)	0.33382 (9)	0.0109 (2)
C1	1.01325 (15)	1.12532 (10)	0.15599 (10)	0.0112 (3)
C2	0.81956 (17)	0.93255 (10)	0.12032 (11)	0.0133 (3)
C3	0.66221 (16)	0.90062 (10)	0.19086 (10)	0.0120 (3)
C4	0.57703 (17)	0.84181 (11)	0.39090 (11)	0.0151 (3)
C5	0.76474 (17)	1.02474 (10)	0.38754 (10)	0.0137 (3)
H2A	0.94160	0.89510	0.16520	0.0160*
H2B	0.78540	0.89820	0.03320	0.0160*
H3A	0.55390	0.95710	0.16510	0.0140*
H3B	0.61320	0.82020	0.16390	0.0140*
H4A	0.61680	0.84390	0.48440	0.0230*
H4B	0.56360	0.75900	0.36190	0.0230*
H4C	0.45320	0.88280	0.36380	0.0230*
H5	0.839 (2)	0.8576 (16)	0.3566 (16)	0.024 (4)*
H5A	0.65260	1.07550	0.35540	0.0210*
H5B	0.87790	1.05780	0.36130	0.0210*
H5C	0.78910	1.02120	0.48110	0.0210*

	U11	U22	U33	U12	U13	U23
S1	0.0125 (1)	0.0164 (2)	0.0171 (1)	0.0012 (1)	0.0001 (1)	0.0039 (1)
N1	0.0124 (4)	0.0083 (4)	0.0120 (4)	−0.0003 (3)	0.0014 (3)	0.0014 (3)
N2	0.0142 (4)	0.0123 (5)	0.0155 (4)	0.0007 (4)	−0.0004 (3)	0.0024 (3)
N3	0.0141 (4)	0.0127 (5)	0.0186 (5)	0.0001 (4)	0.0009 (3)	0.0021 (3)
N4	0.0121 (4)	0.0106 (4)	0.0154 (4)	−0.0002 (3)	0.0020 (3)	0.0014 (3)
N5	0.0122 (4)	0.0089 (4)	0.0115 (4)	0.0003 (3)	0.0025 (3)	0.0003 (3)
C1	0.0132 (4)	0.0099 (5)	0.0110 (4)	−0.0007 (4)	0.0039 (3)	0.0000 (3)
C2	0.0185 (5)	0.0080 (5)	0.0144 (5)	−0.0018 (4)	0.0056 (4)	−0.0008 (4)
C3	0.0143 (5)	0.0108 (5)	0.0101 (4)	−0.0027 (4)	0.0012 (3)	−0.0006 (3)
C4	0.0162 (5)	0.0139 (5)	0.0166 (5)	−0.0007 (4)	0.0065 (4)	0.0028 (4)
C5	0.0170 (5)	0.0101 (5)	0.0137 (5)	−0.0014 (4)	0.0024 (4)	−0.0026 (4)

S1—C1	1.7003 (11)	C2—C3	1.5207 (17)
N1—N2	1.3609 (14)	C2—H2A	0.9900
N1—C1	1.3612 (14)	C2—H2B	0.9900
N1—C2	1.4584 (14)	C3—H3A	0.9900
N2—N3	1.2914 (14)	C3—H3B	0.9900
N3—N4	1.3664 (14)	C4—H4A	0.9800
N4—C1	1.3471 (15)	C4—H4B	0.9800
N5—C3	1.4994 (14)	C4—H4C	0.9800
N5—C4	1.4962 (16)	C5—H5A	0.9800
N5—C5	1.4929 (14)	C5—H5B	0.9800
N5—H5	0.934 (16)	C5—H5C	0.9800
S1···H2A	2.8400	C5···N1	3.1945 (14)
S1···H3Ai	3.0500	C5···N3x	3.1239 (15)
S1···H4Ci	2.8300	C1···H5B	2.6900
S1···H5Ai	3.0400	C1···H5ii	2.830 (18)
S1···H5B	2.9000	C1···H2Biii	2.7300
S1···H3Bii	3.0600	C2···H5B	2.8900
S1···H4Bii	3.0000	H2A···S1	2.8400
S1···H2Biii	3.0800	H2A···H5	2.3600
S1···H4Aiv	2.9400	H2B···S1iii	3.0800
S1···H5Civ	3.0500	H2B···N4iii	2.9400
N1···N4	2.1601 (14)	H2B···C1iii	2.7300
N1···N5	3.2610 (13)	H3A···S1xi	3.0500
N1···C5	3.1945 (14)	H3A···N2	2.7800
N2···C4v	3.3800 (16)	H3A···H4C	2.5300
N2···N4	2.1867 (14)	H3A···H5A	2.4100
N2···C3vi	3.2180 (15)	H3A···N2vi	2.7200
N3···C5vii	3.1239 (15)	H3B···H4B	2.3300
N3···C4v	3.1363 (16)	H3B···S1viii	3.0600
N4···C4ii	3.4054 (16)	H3B···N2vi	2.8600
N4···N1	2.1601 (14)	H4A···H5C	2.3400
N4···N5ii	2.8054 (14)	H4A···S1iv	2.9400
N5···N1	3.2610 (13)	H4B···H3B	2.3300
N5···N4viii	2.8054 (14)	H4B···S1viii	3.0000
N1···H5B	2.6600	H4B···N2ix	2.8800
N2···H3A	2.7800	H4C···S1xi	2.8300
N2···H4Bv	2.8800	H4C···H3A	2.5300
N2···H3Avi	2.7200	H4C···N3ix	2.7900
N2···H3Bvi	2.8600	H5···H2A	2.3600
N3···H4Cv	2.7900	H5···N4viii	1.889 (17)
N3···H5Cvii	2.8100	H5···C1viii	2.830 (18)
N3···H5Avii	2.9000	H5A···S1xi	3.0400
N4···H2Biii	2.9400	H5A···H3A	2.4100
N4···H5ii	1.889 (17)	H5A···N3x	2.9000
C1···C5	3.5255 (16)	H5B···S1	2.9000
C1···C2iii	3.4785 (16)	H5B···N1	2.6600
C2···C1iii	3.4785 (16)	H5B···C1	2.6900
C3···N2vi	3.2180 (15)	H5B···C2	2.8900
C4···N3ix	3.1363 (16)	H5C···H4A	2.3400
C4···N2ix	3.3800 (16)	H5C···S1iv	3.0500
C4···N4viii	3.4054 (16)	H5C···N3x	2.8100
C5···C1	3.5255 (16)
N2—N1—C1	109.70 (9)	C3—C2—H2B	109.00
N2—N1—C2	120.40 (9)	H2A—C2—H2B	108.00
C1—N1—C2	129.63 (10)	N5—C3—H3A	109.00
N1—N2—N3	106.46 (9)	N5—C3—H3B	109.00
N2—N3—N4	110.70 (9)	C2—C3—H3A	109.00
N3—N4—C1	107.34 (9)	C2—C3—H3B	109.00
C3—N5—C4	109.02 (9)	H3A—C3—H3B	108.00
C3—N5—C5	113.32 (8)	N5—C4—H4A	109.00
C4—N5—C5	110.51 (9)	N5—C4—H4B	109.00
C5—N5—H5	108.7 (11)	N5—C4—H4C	109.00
C3—N5—H5	108.2 (10)	H4A—C4—H4B	109.00
C4—N5—H5	106.9 (10)	H4A—C4—H4C	109.00
S1—C1—N4	128.17 (9)	H4B—C4—H4C	109.00
S1—C1—N1	126.03 (9)	N5—C5—H5A	109.00
N1—C1—N4	105.80 (9)	N5—C5—H5B	109.00
N1—C2—C3	114.73 (9)	N5—C5—H5C	109.00
N5—C3—C2	114.26 (9)	H5A—C5—H5B	109.00
N1—C2—H2A	109.00	H5A—C5—H5C	109.00
N1—C2—H2B	109.00	H5B—C5—H5C	109.00
C3—C2—H2A	109.00
C1—N1—N2—N3	−0.17 (12)	N1—N2—N3—N4	−0.04 (12)
C2—N1—N2—N3	−174.75 (10)	N2—N3—N4—C1	0.24 (12)
N2—N1—C1—S1	179.98 (9)	N3—N4—C1—S1	−180.00 (8)
N2—N1—C1—N4	0.31 (12)	N3—N4—C1—N1	−0.33 (12)
C2—N1—C1—S1	−6.09 (17)	C4—N5—C3—C2	−166.23 (9)
C2—N1—C1—N4	174.24 (10)	C5—N5—C3—C2	70.26 (12)
N2—N1—C2—C3	−68.63 (13)	N1—C2—C3—N5	−81.52 (12)
C1—N1—C2—C3	118.00 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N4viii	0.934 (16)	1.889 (17)	2.8054 (14)	166.2 (16)
C2—H2A···S1	0.99	2.84	3.3039 (12)	109
C4—H4C···S1xi	0.98	2.83	3.7275 (13)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯N4i	0.934 (16)	1.889 (17)	2.8054 (14)	166.2 (16)
C4—H4C⋯S1ii	0.98	2.83	3.7275 (13)	153

Symmetry codes: (i) ; (ii) .