organic compounds
1-[2-(Dimethylazaniumyl)ethyl]-1H-1,2,3,4-tetrazole-5-thiolate
aPeriyar Maniammai University, Thanjavur 613 403, Tamil Nadu, India, and bSchool of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamil Nadu, India
*Correspondence e-mail: lvsethu13@gmail.com
In the 5H11N5S, molecules 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).
of the title zwitterion, CCCDC reference: 982929
Related literature
For the biological activity of tetrazoles, see: Juby et al. (1982); Tamilselvi & Mugesh (2009, 2011). For the general existence of 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
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Data collection: APEX2 (Bruker, 2004); cell 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).
Supporting information
CCDC reference: 982929
10.1107/S1600536814001573/bv2228sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001573/bv2228Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001573/bv2228Isup3.cml
The title compound was obtained by dissolving DMETT (Sigma-Aldrich; 43.3mg, 0.25 mmol) in 20 ml of hot methanol, warming the resultant solution over a water bath for half an hour and then keeping it at room temperature for crystallization. After a week's time, colorless prismatic crystals were obtained
The hydrogen atoms for the ammonium group (NH4+) was located in a difference Fourier map and refined freely. All other hydrogen atoms were positioned geometrically (C—H = 0.98–0.99 A) and were refined using a riding model, with Uiso(H) = 1.2Ueq(C) for CH2 or 1.5Ueq(C) for CH3.
A large number of tetrazole derivatives exhibit diverse pharmacological properties (Juby et al., 1982) and some antibiotics with heterocyclic thiol side chains possess antithyroid activity (Tamilselvi & Mugesh, 2009). 1-(2-(Dimethylamino)-ethyl)-1H-tetrazole-5-thione (DMETT) exhibits thiol-thione β-lactamases catalysed hydrolysis of (Tamilselvi & Mugesh, 2011). Cefotiam, a second-generation cephalosporin antibiotic, has a derivative of DMETT as a side chain which is more active against many of the Enterobacteriacea including Enterobacter, E·Coli, Klebsiella, Salmonella and Indole-positive Proteus species (Garcia-Rodriguez et al. 1995; Polis & Tuazon, 1985).
and thiolate anion formation which plays a vital role in the inhibition of the metallo-The current investigation focusses on the supramolecular hydrogen bonded patterns exhibited by the title compound (Scheme. 1).
The title compound (I), 1-[2-(dimethylazaniumyl)ethyl]-1H-1,2,3,4-tetrazole-5-thiolate tetrazole-5-thiolate (DMATT) crystallizes with one molecule in the
and it exists as a zwitterion with the positive charge on the ammonium nitrogen atom and the negative charge on the thiolate sulfur atom (Fig 1).This compound exists as a zwitterion like many other amino compounds reported in the literature (Ruanwas, et al., 2012; Ha, 2012). There is an intramolecular exchange of thiol proton to amino nitrogen and thus thiolate formation, which leads to the generation of a nucleophilic sulfur species (responsible for the inhibition activity). The geometry of the tert- ammonium group is found to be tetrahedral with bond angles ranging from 106.9 (11)–113.32 (9)°. The maximum deviation of the side chain at N1 position from the mean plane of tetrazole ring moiety is found to be 0.313 (10) Å. The molecular confirmation is inferred from the torsion angles N1—C2—C3—N5, C2—C3—N5—C4 and C2—C3—N5—C5 and the values are found to be -81.52 (12)°, -166.23 (9)°, and 70.26 (12)° respectively.
Two inversion related
present in the same plane are linked by a strong N—H···N hydrogen bond involving tert-ammonium group and ring N4i atom [symmetry code: -x + 2, y - 1/2, -z + 1/2] (Table 1). This interaction extends along b axis leading to the generation of a wave like supramolecular chain. The supramolecular chains in the adjacent planes are connected via a weak C—H···S hydrogen bond. This hydrogen bond links one of the methyl C—H groups and S1ii atom [symmetry code: x - 1, y, z] and generates another wave like supramolecular chain extending along a axis. The centrosymmetric N—H···N linkage between two facilitates the effective occurrence of C—H···S hydrogen bond thus forming a ring motif with a graph set of R44(23). This motif exists in both a and b axis and generates a two dimensional network as shown in Fig. 2.For the biological activity of tetrazoles, see: Juby et al. (1982); Tamilselvi & Mugesh (2009, 2011). For the general existence of
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-thion] as a side chain, against enterobacteriacea, see: Garcia-Rodriguez et al. (1995); Polis & Tuazon (1985).Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Spek, 2009) and publCIF (Westrip, 2010).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 |
C5H11N5S | V = 834.89 (2) Å3 |
Mr = 173.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.1021 (1) Å | µ = 0.33 mm−1 |
b = 11.2476 (2) Å | T = 100 K |
c = 10.7045 (2) Å | 0.41 × 0.21 × 0.14 mm |
β = 102.479 (1)° |
Bruker Kappa APEXII CCD diffractometer | 3004 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2618 reflections with I > 2σ(I) |
Tmin = 0.876, Tmax = 0.955 | Rint = 0.027 |
11518 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.48 e Å−3 |
3004 reflections | Δρmin = −0.30 e Å−3 |
106 parameters |
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) |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+2, −y+2, −z; (iv) −x+2, −y+2, −z+1; (v) −x+1, y+1/2, −z+1/2; (vi) −x+1, −y+2, −z; (vii) x, −y+5/2, z−1/2; (viii) −x+2, y−1/2, −z+1/2; (ix) −x+1, y−1/2, −z+1/2; (x) x, −y+5/2, z+1/2; (xi) x−1, y, z. |
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 |
Symmetry codes: (viii) −x+2, y−1/2, −z+1/2; (xi) x−1, y, z. |
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 | 0.9800 | 2.8300 | 3.7275 (13) | 153.00 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x−1, y, z. |
Acknowledgements
The authors thank Dr Babu Varghese and the Sophisticated Analytical Instrument Facility (SAIF), Indian Institute of Technology, Chennai, Tamil Nadu, India, for the data collection.
References
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A large number of tetrazole derivatives exhibit diverse pharmacological properties (Juby et al., 1982) and some antibiotics with heterocyclic thiol side chains possess antithyroid activity (Tamilselvi & Mugesh, 2009). 1-(2-(Dimethylamino)-ethyl)-1H-tetrazole-5-thione (DMETT) exhibits thiol-thione tautomerism and thiolate anion formation which plays a vital role in the inhibition of the metallo-β-lactamases catalysed hydrolysis of cephalosporins (Tamilselvi & Mugesh, 2011). Cefotiam, a second-generation cephalosporin antibiotic, has a derivative of DMETT as a side chain which is more active against many of the Enterobacteriacea including Enterobacter, E·Coli, Klebsiella, Salmonella and Indole-positive Proteus species (Garcia-Rodriguez et al. 1995; Polis & Tuazon, 1985).
The current investigation focusses on the supramolecular hydrogen bonded patterns exhibited by the title compound (Scheme. 1).
The title compound (I), 1-[2-(dimethylazaniumyl)ethyl]-1H-1,2,3,4-tetrazole-5-thiolate tetrazole-5-thiolate (DMATT) crystallizes with one molecule in the asymmetric unit and it exists as a zwitterion with the positive charge on the ammonium nitrogen atom and the negative charge on the thiolate sulfur atom (Fig 1).
This compound exists as a zwitterion like many other amino compounds reported in the literature (Ruanwas, et al., 2012; Ha, 2012). There is an intramolecular exchange of thiol proton to amino nitrogen and thus thiolate formation, which leads to the generation of a nucleophilic sulfur species (responsible for the inhibition activity). The geometry of the tert- ammonium group is found to be tetrahedral with bond angles ranging from 106.9 (11)–113.32 (9)°. The maximum deviation of the side chain at N1 position from the mean plane of tetrazole ring moiety is found to be 0.313 (10) Å. The molecular confirmation is inferred from the torsion angles N1—C2—C3—N5, C2—C3—N5—C4 and C2—C3—N5—C5 and the values are found to be -81.52 (12)°, -166.23 (9)°, and 70.26 (12)° respectively.
Two inversion related zwitterions present in the same plane are linked by a strong N—H···N hydrogen bond involving tert-ammonium group and ring N4i atom [symmetry code: -x + 2, y - 1/2, -z + 1/2] (Table 1). This interaction extends along b axis leading to the generation of a wave like supramolecular chain. The supramolecular chains in the adjacent planes are connected via a weak C—H···S hydrogen bond. This hydrogen bond links one of the methyl C—H groups and S1ii atom [symmetry code: x - 1, y, z] and generates another wave like supramolecular chain extending along a axis. The centrosymmetric N—H···N linkage between two zwitterions facilitates the effective occurrence of C—H···S hydrogen bond thus forming a ring motif with a graph set of R44(23). This motif exists in both a and b axis and generates a two dimensional network as shown in Fig. 2.