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

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Abd El-Alaziz, A.T.; Albayati, M.R.

doi:10.1107/S160053681400347X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o328-o329

doi:10.1107/S160053681400347X

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

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Ahmed T. Abd El-Alaziz ^c and Mustafa R. Albayati ^e ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 13 February 2014; accepted 17 February 2014; online 22 February 2014)

In the title hydrated molecular salt, C₂₂H₁₈BrN₄S⁺·Br⁻·H₂O, the aromatic rings make dihedral angles of 14.20 (12), 34.29 (10) and 68.75 (11)° with the thiazole ring. In the crystal, molecules are linked into chains running parallel to the a axis by association of the bromide ions and the water molecules of crystallization with the cations via N—H⋯O, O—H⋯Br, C—H⋯N and C—H⋯Br hydrogen-bonding interactions. C—H⋯π and C—Br⋯π [3.7426 (11) Å, 161.73 (7)°] interactions are also observed, forming infinite chains extending along the b-axis direction.

CCDC reference: 987315

Related literature

For general background to thiazole compounds, see: Siddiqui et al. (2009 ); Quiroga et al. (2002 ); Hutchinson et al. (2002 ). For the biological activity of thiazoles, see: Sharma et al. (2009 ); Ergenc et al. (1999 ); Bell et al. (1995 ); Patt et al. (1992 ); Jaen et al. (1990 ); Badorc et al. (1997 ); Rudolph et al. (2001 ). For structures with C—Br⋯π interactions, see: Jasinski et al. (2010 ); Zukerman-Schpector et al. (2011 ).

Experimental

Crystal data

C₂₂H₁₈BrN₄S⁺·Br⁻·H₂O
M_r = 548.30
Triclinic, $[P \overline 1]$
a = 5.5768 (6) Å
b = 9.2288 (9) Å
c = 22.574 (2) Å
α = 85.974 (1)°
β = 84.438 (1)°
γ = 79.000 (1)°
V = 1133.51 (19) Å³
Z = 2
Mo Kα radiation
μ = 3.69 mm⁻¹
T = 150 K
0.27 × 0.11 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: numerical (SADABS; Bruker, 2013 ) T_min = 0.390, T_max = 0.760
20898 measured reflections
5870 independent reflections
4807 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.095
S = 1.09
5870 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.94 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Br2	0.85	2.49	3.332 (2)	170
O1—H1B⋯Br2ⁱ	0.85	2.61	3.271 (2)	135
N4—H4⋯O1	0.88	1.95	2.715 (3)	144
C15—H15⋯N2ⁱⁱ	0.95	2.62	3.571 (3)	177
C17—H17B⋯Br2ⁱⁱⁱ	0.98	2.88	3.798 (3)	156
C20—H20⋯Br2^iv	0.95	2.85	3.798 (3)	175
C21—H21⋯Br2^v	0.95	2.92	3.579 (3)	127
C11—H11⋯Cg3ⁱ	0.95	2.93	3.789 (3)	152
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) x, y+1, z; (iv) -x+2, -y+1, -z; (v) x+1, y+1, z.

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 987315

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681400347X/qm2104sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681400347X/qm2104Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681400347X/qm2104Isup3.cml

checkCIF report

Comment top

Thiazoles have shown a broad range of biological applications and activities (Siddiqui et al., 2009; Quiroga et al., 2002; Hutchinson, et al., 2002) including uses for the treatment of inflammation (Sharma et al., 2009), HIV infections (Bell et al., 1995), hypertension (Patt et al., 1992), schizophrenia (Jaen et al., 1990), as hypnotics (Ergenc et al., 1999), as fibrinogen receptor antagonists with antithrombotic activity (Badorc et al., 1997) and as new inhibitors of bacterial DNA gyrase B (Rudolph et al., 2001). In this context we report the synthesis and crystal structure of the title compound.

The N4/C18—C22, C1–C6 and C10–C15 aromatic rings make dihedral angles of 14.20 (12), 34.29 (10) and 68.75 (11)°, respectively, with the (S1/N1/C7–C9) thiazole ring (Fig. 1). The C9–N2–N3–C16, N2–N3–C16–C17, N2–N3–C16–C18 torsion angles are 174.0 (2), -4.0 (4) and 175.0 (5)°, respectively.

The three-dimensional structure of the title compound consists of chains running parallel to the a axis which are formed by association of the bromide ions and the lattice water molecules with the cations via O—H···N, O—H···Br, C—H···N and C—H···Br hydrogen bonding interactions (Table 1 and Figs. 2 & 3). In addition, a C—H···p interaction (Table 1) and a C4—Br1···Cg4 (-1 - x, 1 - y, 1 - z) interaction [Br1···Cg4 = 3.7426 (11) Å and C4—Br1···Cg4 = 161.73 (7)°] (Jasinski et al., 2010; Zukerman-Schpector, et al., 2011) also contribute to the stabilization of the molecular packing.

Related literature top

For general background to thiazole compounds, see: Siddiqui et al. (2009); Quiroga et al. (2002); Hutchinson et al. (2002). For the biological activity of thiazoles, see: Sharma et al. (2009); Ergenc et al. (1999); Bell et al. (1995); Patt et al. (1992); Jaen et al. (1990); Badorc et al. (1997); Rudolph et al. (2001). For structures with C—Br···π interactions, see: Jasinski et al. (2010); Zukerman-Schpector et al. (2011).

Experimental top

A mixture of 270 mg (1 mmol) (2E)-N-phenyl-2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioamide and 278 mg (1 mmol) 2-bromo-1-phenylethanone in absolute ethanol (30 ml) was refluxed for 8 h then cooled to room temperature. A yellow solid precipitated, it was filtered and washed with a small amount of cold ethanol and recrystallized from ethanol to afford good quality orange crystals (M.p. 521–523 K).

¹H-NMR (CDCl₃): δH= 1.63 (br, 1H, OH of H₂O), 2.46 (s,3H, CH₃), 6.41 (s, 1H, thiazole-CH), 6.97–7.02 (m, 2H, Ar—H), 7.21–7.23 (m, 2H, Ar—H), 7.54–7.61 (m, 1H, pyridine-CH), 7.72–7.79 (m, 1H, pyridine-CH), 8.22–8.25 (m, 2H, pyridine-CH), 9.10 (br, 1H, pyridinium-NH).

¹³C-NMR (CDCl₃): δC= 14.02 (CH₃), 104.27 (thiazole-CH), 127.89, 128.12, 128.36, 129.00, 129.92, 130.48, 131.77 (Ar—CH and pyridine-CH), 123.48, 131.98 (Ar—C), 142.04 (pridine-C), 153.27 (thiazole-C4), 156.38 (thiazole-C2).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of the asymmetric unit with 50% probability ellipsoids.
	Fig. 2. Packing viewed down the a axis showing the cation- anion-water chains with hydrogen bonds indicated by dotted lines.
	Fig. 3. Packing viewed down the b axis giving a side view of the chains.

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

Crystal data top

C₂₂H₁₈BrN₄S⁺·Br⁻·H₂O	Z = 2
M_r = 548.30	F(000) = 548
Triclinic, P1	D_x = 1.598 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5768 (6) Å	Cell parameters from 9919 reflections
b = 9.2288 (9) Å	θ = 2.4–29.1°
c = 22.574 (2) Å	µ = 3.69 mm⁻¹
α = 85.974 (1)°	T = 150 K
β = 84.438 (1)°	Column, orange
γ = 79.000 (1)°	0.27 × 0.11 × 0.08 mm
V = 1133.51 (19) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	5870 independent reflections
Radiation source: fine-focus sealed tube	4807 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 29.3°, θ_min = 1.8°
Absorption correction: numerical (SADABS; Bruker, 2013)	h = −7→7
T_min = 0.390, T_max = 0.760	k = −12→12
20898 measured reflections	l = −30→30

Refinement top

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.095	W = 1/[Σ²(FO²) + (0.0532P)² + 0.0059P] WHERE P = (FO² + 2FC²)/3
S = 1.09	(Δ/σ)_max < 0.001
5870 reflections	Δρ_max = 0.94 e Å⁻³
272 parameters	Δρ_min = −0.49 e Å⁻³
0 restraints

Crystal data top

C₂₂H₁₈BrN₄S⁺·Br⁻·H₂O	γ = 79.000 (1)°
M_r = 548.30	V = 1133.51 (19) Å³
Triclinic, P1	Z = 2
a = 5.5768 (6) Å	Mo Kα radiation
b = 9.2288 (9) Å	µ = 3.69 mm⁻¹
c = 22.574 (2) Å	T = 150 K
α = 85.974 (1)°	0.27 × 0.11 × 0.08 mm
β = 84.438 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	5870 independent reflections
Absorption correction: numerical (SADABS; Bruker, 2013)	4807 reflections with I > 2σ(I)
T_min = 0.390, T_max = 0.760	R_int = 0.038
20898 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.09	Δρ_max = 0.94 e Å⁻³
5870 reflections	Δρ_min = −0.49 e Å⁻³
272 parameters

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 8 sec/frame.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	−0.67572 (4)	0.25013 (3)	0.47615 (2)	0.0304 (1)
S1	0.27834 (11)	0.54280 (7)	0.18810 (2)	0.0295 (2)
N1	0.0981 (3)	0.6483 (2)	0.28912 (8)	0.0239 (5)
N2	0.3783 (4)	0.7847 (2)	0.23756 (8)	0.0277 (6)
N3	0.5417 (4)	0.7723 (2)	0.18707 (8)	0.0287 (6)
N4	0.8686 (4)	0.7361 (2)	0.09224 (8)	0.0289 (6)
C1	−0.1818 (4)	0.4718 (2)	0.33067 (10)	0.0244 (6)
C2	−0.1555 (4)	0.4784 (2)	0.39151 (10)	0.0246 (6)
C3	−0.3043 (4)	0.4146 (2)	0.43439 (10)	0.0254 (6)
C4	−0.4804 (4)	0.3437 (2)	0.41671 (10)	0.0245 (6)
C5	−0.5136 (4)	0.3367 (2)	0.35703 (10)	0.0276 (7)
C6	−0.3638 (4)	0.4001 (2)	0.31457 (10)	0.0266 (6)
C7	0.0640 (4)	0.4595 (3)	0.23186 (10)	0.0289 (7)
C8	−0.0151 (4)	0.5258 (2)	0.28337 (10)	0.0247 (6)
C9	0.2610 (4)	0.6731 (2)	0.24143 (9)	0.0253 (7)
C10	0.0341 (4)	0.7538 (2)	0.33465 (9)	0.0223 (6)
C11	0.2053 (4)	0.7667 (3)	0.37362 (10)	0.0265 (7)
C12	0.1458 (4)	0.8746 (3)	0.41508 (10)	0.0303 (7)
C13	−0.0796 (4)	0.9677 (3)	0.41774 (10)	0.0308 (7)
C14	−0.2523 (4)	0.9507 (3)	0.37950 (11)	0.0302 (7)
C15	−0.1951 (4)	0.8427 (2)	0.33767 (10)	0.0259 (6)
C16	0.6559 (5)	0.8811 (3)	0.17393 (10)	0.0288 (7)
C17	0.6171 (6)	1.0229 (3)	0.20592 (12)	0.0415 (9)
C18	0.8431 (5)	0.8590 (3)	0.12317 (10)	0.0287 (7)
C19	1.0414 (5)	0.7011 (3)	0.04748 (11)	0.0357 (8)
C20	1.2093 (5)	0.7923 (3)	0.03072 (11)	0.0395 (8)
C21	1.1876 (6)	0.9201 (3)	0.06046 (12)	0.0430 (9)
C22	1.0058 (5)	0.9543 (3)	0.10605 (11)	0.0374 (8)
Br2	0.27139 (5)	0.28139 (3)	0.09148 (2)	0.0383 (1)
O1	0.7203 (4)	0.4762 (2)	0.08156 (10)	0.0527 (8)
H2	−0.03430	0.52720	0.40350	0.0300*
H3	−0.28530	0.41960	0.47550	0.0310*
H4	0.77020	0.67170	0.09920	0.0350*
H5	−0.63730	0.28920	0.34550	0.0330*
H6	−0.38490	0.39500	0.27360	0.0320*
H7	0.00780	0.37530	0.22060	0.0350*
H11	0.36070	0.70280	0.37190	0.0320*
H12	0.26180	0.88460	0.44200	0.0360*
H13	−0.11680	1.04310	0.44560	0.0370*
H14	−0.40940	1.01290	0.38190	0.0360*
H15	−0.31250	0.83040	0.31150	0.0310*
H17A	0.48760	1.02160	0.23850	0.0620*
H17B	0.56860	1.10700	0.17790	0.0620*
H17C	0.76970	1.03220	0.22220	0.0620*
H19	1.04880	0.61340	0.02720	0.0430*
H20	1.33540	0.76760	−0.00030	0.0470*
H21	1.29900	0.98550	0.04950	0.0520*
H22	0.99180	1.04350	0.12580	0.0450*
H1A	0.59280	0.43750	0.08470	0.0630*
H1B	0.81640	0.42050	0.10420	0.0630*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0262 (1)	0.0324 (1)	0.0331 (1)	−0.0090 (1)	0.0018 (1)	−0.0010 (1)
S1	0.0374 (3)	0.0343 (3)	0.0186 (3)	−0.0109 (2)	0.0009 (2)	−0.0075 (2)
N1	0.0252 (10)	0.0272 (9)	0.0205 (9)	−0.0067 (8)	−0.0009 (7)	−0.0059 (7)
N2	0.0317 (11)	0.0306 (10)	0.0216 (9)	−0.0085 (8)	0.0009 (8)	−0.0043 (7)
N3	0.0340 (11)	0.0329 (10)	0.0211 (9)	−0.0106 (8)	−0.0008 (8)	−0.0049 (8)
N4	0.0347 (11)	0.0322 (10)	0.0237 (9)	−0.0165 (9)	−0.0011 (8)	−0.0027 (8)
C1	0.0233 (11)	0.0221 (10)	0.0274 (11)	−0.0021 (8)	−0.0021 (9)	−0.0042 (8)
C2	0.0233 (11)	0.0263 (11)	0.0252 (11)	−0.0055 (9)	−0.0013 (9)	−0.0069 (8)
C3	0.0253 (11)	0.0281 (11)	0.0225 (10)	−0.0032 (9)	−0.0011 (9)	−0.0048 (8)
C4	0.0207 (10)	0.0230 (10)	0.0283 (11)	−0.0018 (8)	0.0015 (9)	−0.0021 (8)
C5	0.0251 (11)	0.0251 (11)	0.0345 (12)	−0.0064 (9)	−0.0066 (9)	−0.0041 (9)
C6	0.0253 (11)	0.0288 (11)	0.0258 (11)	−0.0029 (9)	−0.0035 (9)	−0.0055 (9)
C7	0.0359 (13)	0.0313 (12)	0.0227 (11)	−0.0132 (10)	−0.0028 (9)	−0.0051 (9)
C8	0.0260 (11)	0.0271 (11)	0.0227 (10)	−0.0060 (9)	−0.0056 (8)	−0.0047 (8)
C9	0.0269 (12)	0.0301 (12)	0.0194 (10)	−0.0044 (9)	−0.0038 (8)	−0.0039 (8)
C10	0.0243 (11)	0.0236 (10)	0.0194 (10)	−0.0058 (8)	0.0012 (8)	−0.0043 (8)
C11	0.0208 (11)	0.0348 (12)	0.0247 (11)	−0.0053 (9)	−0.0023 (9)	−0.0054 (9)
C12	0.0295 (12)	0.0401 (13)	0.0243 (11)	−0.0118 (10)	−0.0020 (9)	−0.0087 (10)
C13	0.0337 (13)	0.0337 (12)	0.0275 (12)	−0.0120 (10)	0.0034 (10)	−0.0112 (9)
C14	0.0260 (12)	0.0258 (12)	0.0378 (13)	−0.0025 (9)	0.0009 (10)	−0.0059 (9)
C15	0.0253 (11)	0.0282 (11)	0.0260 (11)	−0.0075 (9)	−0.0045 (9)	−0.0029 (9)
C16	0.0384 (13)	0.0280 (11)	0.0214 (10)	−0.0098 (10)	−0.0034 (9)	0.0000 (9)
C17	0.0620 (19)	0.0294 (13)	0.0329 (13)	−0.0115 (12)	0.0041 (12)	−0.0037 (10)
C18	0.0389 (13)	0.0281 (11)	0.0216 (10)	−0.0115 (10)	−0.0057 (9)	−0.0004 (9)
C19	0.0446 (15)	0.0396 (14)	0.0264 (12)	−0.0169 (12)	0.0025 (11)	−0.0094 (10)
C20	0.0468 (16)	0.0459 (15)	0.0293 (13)	−0.0221 (13)	0.0086 (11)	−0.0063 (11)
C21	0.0525 (17)	0.0473 (16)	0.0358 (14)	−0.0298 (13)	0.0055 (12)	−0.0051 (12)
C22	0.0535 (17)	0.0340 (13)	0.0296 (13)	−0.0224 (12)	0.0020 (11)	−0.0033 (10)
Br2	0.0409 (2)	0.0393 (2)	0.0399 (2)	−0.0198 (1)	0.0017 (1)	−0.0117 (1)
O1	0.0430 (12)	0.0436 (12)	0.0761 (15)	−0.0216 (9)	0.0117 (10)	−0.0213 (10)

Geometric parameters (Å, º) top

Br1—C4	1.909 (2)	C13—C14	1.391 (3)
S1—C7	1.735 (2)	C14—C15	1.393 (3)
S1—C9	1.744 (2)	C16—C18	1.471 (4)
O1—H1A	0.8500	C16—C17	1.508 (4)
O1—H1B	0.8500	C18—C22	1.391 (4)
N1—C10	1.438 (3)	C19—C20	1.384 (4)
N1—C9	1.375 (3)	C20—C21	1.378 (4)
N1—C8	1.415 (3)	C21—C22	1.381 (4)
N2—C9	1.315 (3)	C2—H2	0.9500
N2—N3	1.386 (3)	C3—H3	0.9500
N3—C16	1.291 (3)	C5—H5	0.9500
N4—C19	1.339 (3)	C6—H6	0.9500
N4—C18	1.351 (3)	C7—H7	0.9500
N4—H4	0.8800	C11—H11	0.9500
C1—C2	1.402 (3)	C12—H12	0.9500
C1—C8	1.471 (3)	C13—H13	0.9500
C1—C6	1.401 (3)	C14—H14	0.9500
C2—C3	1.387 (3)	C15—H15	0.9500
C3—C4	1.382 (3)	C17—H17C	0.9800
C4—C5	1.385 (3)	C17—H17A	0.9800
C5—C6	1.383 (3)	C17—H17B	0.9800
C7—C8	1.349 (3)	C19—H19	0.9500
C10—C11	1.386 (3)	C20—H20	0.9500
C10—C15	1.379 (3)	C21—H21	0.9500
C11—C12	1.386 (4)	C22—H22	0.9500
C12—C13	1.379 (3)

C7—S1—C9	90.19 (11)	N4—C18—C22	116.9 (2)
H1A—O1—H1B	104.00	N4—C19—C20	120.2 (2)
C8—N1—C10	126.06 (18)	C19—C20—C21	117.8 (3)
C9—N1—C10	119.83 (17)	C20—C21—C22	120.7 (3)
C8—N1—C9	113.57 (17)	C18—C22—C21	120.4 (2)
N3—N2—C9	108.59 (17)	C3—C2—H2	120.00
N2—N3—C16	116.19 (19)	C1—C2—H2	120.00
C18—N4—C19	123.9 (2)	C2—C3—H3	120.00
C19—N4—H4	113.00	C4—C3—H3	120.00
C18—N4—H4	123.00	C6—C5—H5	121.00
C2—C1—C6	118.1 (2)	C4—C5—H5	121.00
C6—C1—C8	118.7 (2)	C5—C6—H6	119.00
C2—C1—C8	123.0 (2)	C1—C6—H6	119.00
C1—C2—C3	120.8 (2)	S1—C7—H7	123.00
C2—C3—C4	119.4 (2)	C8—C7—H7	123.00
C3—C4—C5	121.4 (2)	C10—C11—H11	121.00
Br1—C4—C5	119.76 (16)	C12—C11—H11	121.00
Br1—C4—C3	118.87 (17)	C13—C12—H12	120.00
C4—C5—C6	118.9 (2)	C11—C12—H12	120.00
C1—C6—C5	121.5 (2)	C12—C13—H13	120.00
S1—C7—C8	113.51 (19)	C14—C13—H13	120.00
N1—C8—C7	111.7 (2)	C15—C14—H14	120.00
N1—C8—C1	123.17 (18)	C13—C14—H14	120.00
C1—C8—C7	124.91 (19)	C10—C15—H15	120.00
N1—C9—N2	122.65 (18)	C14—C15—H15	120.00
S1—C9—N2	126.31 (16)	C16—C17—H17B	110.00
S1—C9—N1	111.01 (15)	C16—C17—H17C	109.00
C11—C10—C15	121.3 (2)	H17A—C17—H17B	109.00
N1—C10—C11	119.52 (19)	H17A—C17—H17C	109.00
N1—C10—C15	119.14 (19)	H17B—C17—H17C	109.00
C10—C11—C12	118.8 (2)	C16—C17—H17A	109.00
C11—C12—C13	120.8 (2)	N4—C19—H19	120.00
C12—C13—C14	119.7 (2)	C20—C19—H19	120.00
C13—C14—C15	120.1 (2)	C21—C20—H20	121.00
C10—C15—C14	119.2 (2)	C19—C20—H20	121.00
C17—C16—C18	118.8 (2)	C20—C21—H21	120.00
N3—C16—C18	114.8 (2)	C22—C21—H21	120.00
N3—C16—C17	126.3 (2)	C18—C22—H22	120.00
N4—C18—C16	119.0 (2)	C21—C22—H22	120.00
C16—C18—C22	124.0 (2)

C9—S1—C7—C8	−0.05 (19)	C2—C1—C8—C7	141.2 (2)
C7—S1—C9—N1	0.22 (17)	C6—C1—C8—N1	151.9 (2)
C7—S1—C9—N2	−177.7 (2)	C6—C1—C8—C7	−33.7 (3)
C9—N1—C8—C1	175.39 (19)	C1—C2—C3—C4	0.0 (3)
C9—N1—C8—C7	0.3 (3)	C2—C3—C4—Br1	177.72 (15)
C10—N1—C8—C1	−13.1 (3)	C2—C3—C4—C5	−0.9 (3)
C10—N1—C8—C7	171.8 (2)	Br1—C4—C5—C6	−177.46 (15)
C8—N1—C9—S1	−0.3 (2)	C3—C4—C5—C6	1.1 (3)
C8—N1—C9—N2	177.7 (2)	C4—C5—C6—C1	−0.5 (3)
C10—N1—C9—S1	−172.41 (15)	S1—C7—C8—N1	−0.1 (2)
C10—N1—C9—N2	5.6 (3)	S1—C7—C8—C1	−175.12 (18)
C8—N1—C10—C11	117.6 (2)	N1—C10—C11—C12	176.4 (2)
C8—N1—C10—C15	−63.9 (3)	C15—C10—C11—C12	−2.0 (3)
C9—N1—C10—C11	−71.4 (3)	N1—C10—C15—C14	−176.3 (2)
C9—N1—C10—C15	107.1 (2)	C11—C10—C15—C14	2.1 (3)
C9—N2—N3—C16	174.0 (2)	C10—C11—C12—C13	0.1 (4)
N3—N2—C9—S1	−7.0 (3)	C11—C12—C13—C14	1.8 (4)
N3—N2—C9—N1	175.30 (19)	C12—C13—C14—C15	−1.7 (4)
N2—N3—C16—C17	−4.0 (4)	C13—C14—C15—C10	−0.2 (3)
N2—N3—C16—C18	175.0 (2)	N3—C16—C18—N4	4.8 (4)
C19—N4—C18—C16	−176.2 (2)	N3—C16—C18—C22	−172.3 (2)
C19—N4—C18—C22	1.1 (4)	C17—C16—C18—N4	−176.2 (2)
C18—N4—C19—C20	0.6 (4)	C17—C16—C18—C22	6.8 (4)
C6—C1—C2—C3	0.5 (3)	N4—C18—C22—C21	−1.7 (4)
C8—C1—C2—C3	−174.40 (18)	C16—C18—C22—C21	175.4 (3)
C2—C1—C6—C5	−0.3 (3)	N4—C19—C20—C21	−1.6 (4)
C8—C1—C6—C5	174.87 (18)	C19—C20—C21—C22	0.9 (4)
C2—C1—C8—N1	−33.2 (3)	C20—C21—C22—C18	0.8 (4)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Br2	0.85	2.49	3.332 (2)	170
O1—H1B···Br2ⁱ	0.85	2.61	3.271 (2)	135
N4—H4···O1	0.88	1.95	2.715 (3)	144
C15—H15···N2ⁱⁱ	0.95	2.62	3.571 (3)	177
C17—H17A···N2	0.98	2.38	2.798 (4)	105
C17—H17B···Br2ⁱⁱⁱ	0.98	2.88	3.798 (3)	156
C19—H19···O1	0.95	2.59	3.006 (3)	107
C20—H20···Br2^iv	0.95	2.85	3.798 (3)	175
C21—H21···Br2^v	0.95	2.92	3.579 (3)	127
C11—H11···Cg3ⁱ	0.95	2.93	3.789 (3)	152

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x, y+1, z; (iv) −x+2, −y+1, −z; (v) x+1, y+1, z.

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Br2	0.85	2.49	3.332 (2)	170
O1—H1B···Br2ⁱ	0.85	2.61	3.271 (2)	135
N4—H4···O1	0.88	1.95	2.715 (3)	144
C15—H15···N2ⁱⁱ	0.95	2.62	3.571 (3)	177
C17—H17B···Br2ⁱⁱⁱ	0.98	2.88	3.798 (3)	156
C20—H20···Br2^iv	0.95	2.85	3.798 (3)	175
C21—H21···Br2^v	0.95	2.92	3.579 (3)	127
C11—H11···Cg3ⁱ	0.95	2.93	3.789 (3)	152

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x, y+1, z; (iv) −x+2, −y+1, −z; (v) x+1, y+1, z.

Acknowledgements

Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study.

References

Badorc, A., Bordes, M. F., De Cointet, P., Savi, P., Bernat, A., Lale, A., Petitou, M., Maffrand, J. P. & Herbert, J. M. (1997). J. Med. Chem. 40, 3393–3401. CrossRef CAS PubMed Web of Science Google Scholar
Bell, F. W., Cantrell, A. S., Hogberg, M., Jaskunas, S. R., Johansson, N. G., Jordon, C. L., Kinnick, M. D., Lind, P., Morin, J. M., Noreen, R., Oberg, B., Palkowitz, J. A., Parrish, C. A., Pranc, P., Sahlberg, C., Ternansky, R. J., Vasileff, R. T., Vrang, L., West, S. J., Zhang, H. & Zhou, X. X. (1995). J. Med. Chem. 38, 4929–4936. CrossRef CAS PubMed Web of Science Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ergenc, N., Capan, G., Gunay, N. S., Ozkirimli, S., Gungor, M., Ozbey, S. & Kendi, E. (1999). Arch. Pharm. Pharm. Med. Chem. 332, 343–347. CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hutchinson, I., Jennings, S. A., Vishnuvajjala, B. R., Westwell, A. D. & Stevens, M. F. G. (2002). J. Med. Chem. 45, 744–747. Web of Science CrossRef PubMed CAS Google Scholar
Jaen, J. C., Wise, L. D., Caprathe, B. W., Tecle, H., Bergmeier, S., Humblet, C. C., Heffner, T. G., Meltzner, L. T. & Pugsley, T. A. (1990). J. Med. Chem. 33, 311–317. CrossRef PubMed CAS Web of Science Google Scholar
Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o2018. Web of Science CSD CrossRef IUCr Journals Google Scholar
Patt, W. C., Hamilton, H. W., Taylor, M. D., Ryan, M. J., Taylor, D. J., Connolly, C. J. C., Doherty, A. M., Klutchko, S. R., Sircar, I., Steinbaugh, B. A., Batley, B. L., Painchaud, C. A., Rapundalo, S. T., Michniewicz, B. M. & Olson, S. C. J. (1992). J. Med. Chem. 35, 2562–2572. CrossRef PubMed CAS Web of Science Google Scholar
Quiroga, J., Hernandez, P., Insuasty, B., Abonia, R., Cobo, J., Sanchez, A., Nogueras, M. & Low, J. N. (2002). J. Chem. Soc. Perkin Trans. 1, 4, 555–559. Web of Science CSD CrossRef Google Scholar
Rudolph, J., Theis, H., Hanke, R., Endermann, R., Johannsen, L. & Geschke, F. U. (2001). J. Med. Chem. 44, 619–626. Web of Science CrossRef PubMed CAS Google Scholar
Sharma, R. N., Xavier, F. P., Vasu, K. K., Chaturvedi, S. C. & Pancholi, S. S. (2009). J. Enzyme Inhib. Med. Chem. 24, 890–897. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siddiqui, N., Arshad, M. F., Ahsan, W. & Alam, M. S. (2009). IJPSDR, 1, 136–143. CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zukerman-Schpector, J., De Simone, C. A., Olivato, P. R., Cerqueira, C. R. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o1099–o1100. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 3| March 2014| Pages o328-o329

doi:10.1107/S160053681400347X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

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Refinement

Supporting information

Acknowledgements

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organic compounds

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