2-((1E)-1-{2-[(2Z)-3,4-Diphenyl-2,3-di­hydro-1,3-thia­zol-2-yl­idene]hydrazin-1-yl­idene}eth­yl)pyridin-1-ium bromide monohydrate

Mehmet Akkurt; Joel T Mague; Shaaban K Mohamed; Alaa A Hassan; Mustafa R Albayati

doi:10.1107/S1600536814006229

. 2014 Mar 26;70(Pt 4):o478–o479. doi: 10.1107/S1600536814006229

2-((1E)-1-{2-[(2Z)-3,4-Diphenyl-2,3-dihydro-1,3-thiazol-2-ylidene]hydrazin-1-ylidene}ethyl)pyridin-1-ium bromide monohydrate

Mehmet Akkurt ^a, Joel T Mague ^b, Shaaban K Mohamed ^c,^d, Alaa A Hassan ^d, Mustafa R Albayati ^e,^*

PMCID: PMC3998596 PMID: 24826173

Abstract

In the title compound, C₂₂H₁₉N₄S⁺·Br⁻·H₂O, the dihedral angles between the phenyl groups and the mean plane of the thiazolylidene ring are 34.69 (13) and 64.27 (13)°, respectively, while that between the thiazolylidene and pyridinium rings is 14.73 (13)°. In the crystal, zigzag chains of alternating bromide ions and water molecules associate through O—H⋯Br interactions run in channels approximately parallel to the b axis. These chains help form parallel chains of cations through N—H⋯O, C—H⋯N and C—H⋯Br hydrogen bonds.

Related literature

For the synthesis of thiazoles see: Zambon et al. (2008 ▶); Franklin et al. (2008 ▶); Karegoudar et al. (2008 ▶); Ochiai et al. (2003 ▶). For the biological significance of thiazole scaffold compounds, see: Masquelin & Obrecht (2001 ▶); Hirai et al. (1980 ▶); Ali & El–Kazak (2010 ▶); Andreani et al. (1996 ▶, 2008 ▶); Budriesi et al. (2008 ▶); Walczynski et al. (2005 ▶). For similar structures, see: Mague et al. (2014 ▶); Mohamed et al. (2013a ▶,b ▶).

Experimental

Crystal data

C₂₂H₁₉N₄S⁺·Br⁻·H₂O
M _r = 469.40
Orthorhombic,
a = 21.8890 (17) Å
b = 5.7384 (4) Å
c = 16.6941 (13) Å
V = 2096.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.08 mm⁻¹
T = 150 K
0.19 × 0.08 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T _min = 0.69, T _max = 0.89
35645 measured reflections
5394 independent reflections
4943 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.060
S = 1.05
5394 reflections
263 parameters
71 restraints
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack parameter determined using 2220 quotients [(I ⁺)−(I ⁻)]/[(I ⁺)+(I ⁻)] (Parsons et al., 2013 ▶)
Absolute structure parameter: 0.011 (4)

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814006229/xu5779sup1.cif

e-70-0o478-sup1.cif^{(29.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006229/xu5779Isup2.hkl

e-70-0o478-Isup2.hkl^{(295.7KB, hkl)}

Click here for additional data file.^{(7.8KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814006229/xu5779Isup3.cml

CCDC reference: 992782

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—H1A⋯Br1	0.84	2.45	3.276 (2)	170
O1—H1B⋯Br1ⁱ	0.84	2.49	3.330 (2)	174
N4—H4⋯O1ⁱⁱ	0.89	1.98	2.729 (3)	141
C15—H15⋯N2ⁱ	0.95	2.62	3.566 (4)	178
C20—H20⋯Br1ⁱⁱⁱ	0.95	2.72	3.645 (3)	166

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

Acknowledgments

We gratefully acknowledge Manchester Metropolitan University, Tulane University and Erciyes University for supporting this study.

supplementary crystallographic information

1. Comment

Several methods for the synthesis of thiazole derivatives have been developed (Zambon et al., 2008; Franklin et al., 2008; Karegoudar et al., 2008) with the most widely used method being the Hantzsch's synthesis utilizing thioamides and α–halocarbonyl compounds as the starting materials (Ochiai et al., 2003). 1,3–Thiazole scaffold compounds are present in many pharmacologically active substances (Masquelin & Obrecht, 2001). They have found to possess strong anti–inflammatory (Hirai et al., 1980), antimicrobial (Ali & El–Kazak, 2010), antitumor (Andreani et al., 2008) and selective cardiodepressant activities (Budriesi et al., 2008). Other compounds containing the thiazole ring have been reported as being histamine H3 antagonists (Walczynski et al., 2005) and herbicidals (Andreani et al., 1996). In view of these findings and as part of our efforts (Mague et al., 2014; Mohamed et al., 2013a,b) to identify new candidates that may be of value in designing new and potent antimicrobial agents we report the synthesis and crystal structure of the title compound.

In the title compound (I, Fig. 1), the dihedral angle between the S1/N1C1–C3 thiazolylidene and N4/C18–C22 pyridinium rings is 14.73 (13)° while that between the phenyl groups C4–C9 and C10–C15 and the mean plane of the thiazolylidene ring are, respectively, 34.69 (13) and 64.27 (13)°. The N1–C3–N2–N3, C3–N2–N3–C16, N2–N3–C16–C17, N2–N3–C16–C18 and N3–C16–C18–C19 torsion angles are 174.4 (2), -172.8 (2), 5.7 (4), -174.3 (2) and 170.7 (3) °, respectively. The bond lengths and bond angles in (I) are normal and comparable to those previously reported for similar structures (Mague et al., 2014; Mohamed et al., 2013a,b).

In the crystal, zigzag chains of alternating bromide ions and water molecules associated through O—H···Br interactions run in channels approximately parallel to the b axis. These chains help form parallel chains of cations through N—H···O, C—H···N and C—H···Br hydrogen bonds (Fig. 2 and Table 1).

2. Experimental

The title compound has been prepared according to our reported method (Mohamed et al., 2013b). Orange crystals suitable for X-ray diffraction (m.p.: 507 K) have been obtained by crystallization of the crude product (I) from ethanol.