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

Akkurt, M.; Mague, J.T.; Mohamed, S.K.; Hassan, A.A.; Albayati, M.R.

doi:10.1107/S1600536814006229

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Pages o478-o479

doi:10.1107/S1600536814006229

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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 and Mustafa R. Albayati ^e ^*

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

(Received 11 March 2014; accepted 20 March 2014; online 26 March 2014)

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.

CCDC reference: 992782

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, P n a 2₁
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[F² > 2σ(F²)] = 0.027
wR(F²) = 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)

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
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) $[-x+{\script{3\over 2}}, y-{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

CCDC reference: 992782

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814006229/xu5779sup1.cif

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

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

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

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

Figures top

	Fig. 1. Perspective view of the asymmetric unit showing one of the O—H···Br interactions as a dotted line. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing viewed down the b axis showing the interionic interactions as dotted lines (O—H···Br, orange; N—H···O, blue; C—H···Br, green; C—H···N, grey.

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 top

Crystal data top

C₂₂H₁₉N₄S⁺·Br⁻·H₂O	F(000) = 960
M_r = 469.40	D_x = 1.487 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 9578 reflections
a = 21.8890 (17) Å	θ = 2.2–28.6°
b = 5.7384 (4) Å	µ = 2.08 mm⁻¹
c = 16.6941 (13) Å	T = 150 K
V = 2096.9 (3) Å³	Column, orange
Z = 4	0.19 × 0.08 × 0.06 mm

Data collection top

Bruker SMART APEX CCD diffractometer	5394 independent reflections
Radiation source: fine-focus sealed tube	4943 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 8.3660 pixels mm^-1	θ_max = 28.9°, θ_min = 1.9°
ϕ and ω scans	h = −29→29
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −7→7
T_min = 0.69, T_max = 0.89	l = −22→21
35645 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.027	w = 1/[σ²(F_o²) + (0.0251P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.060	(Δ/σ)_max = 0.001
S = 1.05	Δρ_max = 0.60 e Å⁻³
5394 reflections	Δρ_min = −0.18 e Å⁻³
263 parameters	Absolute structure: Flack parameter determined using 2220 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
71 restraints	Absolute structure parameter: 0.011 (4)

Crystal data top

C₂₂H₁₉N₄S⁺·Br⁻·H₂O	V = 2096.9 (3) Å³
M_r = 469.40	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 21.8890 (17) Å	µ = 2.08 mm⁻¹
b = 5.7384 (4) Å	T = 150 K
c = 16.6941 (13) Å	0.19 × 0.08 × 0.06 mm

Data collection top

Bruker SMART APEX CCD diffractometer	5394 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	4943 reflections with I > 2σ(I)
T_min = 0.69, T_max = 0.89	R_int = 0.046
35645 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.060	Δρ_max = 0.60 e Å⁻³
S = 1.05	Δρ_min = −0.18 e Å⁻³
5394 reflections	Absolute structure: Flack parameter determined using 2220 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
263 parameters	Absolute structure parameter: 0.011 (4)
71 restraints

Special details top

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
S1	0.61850 (3)	0.09593 (11)	0.85092 (4)	0.0229 (2)
N1	0.51800 (10)	0.2131 (3)	0.78160 (14)	0.0192 (6)
N2	0.57004 (10)	−0.0860 (4)	0.71385 (14)	0.0217 (6)
N3	0.61924 (10)	−0.2324 (4)	0.72594 (15)	0.0205 (6)
N4	0.71202 (10)	−0.5216 (4)	0.75415 (13)	0.0213 (6)
C1	0.57446 (12)	0.3189 (4)	0.89084 (17)	0.0230 (8)
C2	0.52293 (11)	0.3602 (4)	0.84921 (17)	0.0206 (7)
C3	0.56577 (11)	0.0597 (4)	0.77396 (16)	0.0194 (7)
C4	0.47512 (11)	0.5271 (4)	0.87249 (16)	0.0205 (7)
C5	0.49212 (15)	0.7326 (4)	0.91199 (19)	0.0265 (8)
C6	0.44860 (15)	0.8887 (5)	0.93869 (18)	0.0310 (9)
C7	0.38714 (15)	0.8462 (5)	0.92659 (19)	0.0314 (9)
C8	0.36944 (14)	0.6413 (5)	0.88887 (18)	0.0281 (8)
C9	0.41249 (12)	0.4834 (5)	0.86216 (16)	0.0236 (8)
C10	0.47325 (11)	0.2338 (4)	0.71884 (18)	0.0194 (7)
C11	0.43411 (12)	0.0479 (5)	0.70314 (18)	0.0259 (8)
C12	0.39293 (13)	0.0661 (5)	0.6403 (2)	0.0337 (10)
C13	0.39056 (15)	0.2685 (6)	0.5947 (2)	0.0362 (10)
C14	0.42835 (15)	0.4519 (6)	0.61191 (18)	0.0351 (10)
C15	0.47038 (12)	0.4360 (5)	0.67431 (16)	0.0247 (8)
C16	0.63290 (12)	−0.3691 (5)	0.66705 (16)	0.0208 (7)
C17	0.60418 (15)	−0.3685 (6)	0.58542 (18)	0.0324 (9)
C18	0.68144 (11)	−0.5385 (4)	0.68431 (15)	0.0195 (7)
C19	0.69676 (14)	−0.7211 (5)	0.63304 (17)	0.0252 (8)
C20	0.74126 (14)	−0.8816 (5)	0.65600 (18)	0.0290 (9)
C21	0.77059 (14)	−0.8562 (6)	0.7283 (2)	0.0302 (9)
C22	0.75536 (14)	−0.6732 (5)	0.77747 (19)	0.0265 (9)
Br1	0.72775 (2)	0.20153 (4)	0.99633 (2)	0.0276 (1)
O1	0.71716 (11)	0.6961 (3)	0.89932 (15)	0.0354 (7)
H1	0.58560	0.40360	0.93750	0.0280*
H4	0.70300	−0.40570	0.78750	0.0260*
H5	0.53420	0.76510	0.92050	0.0320*
H6	0.46100	1.02660	0.96560	0.0370*
H7	0.35740	0.95570	0.94390	0.0380*
H8	0.32720	0.60930	0.88140	0.0340*
H9	0.39960	0.34400	0.83650	0.0280*
H11	0.43560	−0.08920	0.73500	0.0310*
H12	0.36630	−0.05990	0.62840	0.0400*
H13	0.36260	0.27960	0.55140	0.0430*
H14	0.42590	0.59080	0.58110	0.0420*
H15	0.49680	0.56290	0.68610	0.0300*
H17A	0.57680	−0.23420	0.58060	0.0490*
H17B	0.58080	−0.51260	0.57790	0.0490*
H17C	0.63620	−0.35830	0.54450	0.0490*
H19	0.67700	−0.73610	0.58270	0.0300*
H20	0.75130	−1.00820	0.62180	0.0350*
H21	0.80110	−0.96440	0.74420	0.0360*
H22	0.77530	−0.65380	0.82760	0.0320*
H1A	0.72270	0.57880	0.92850	0.0420*
H1B	0.71770	0.81980	0.92620	0.0420*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0172 (3)	0.0289 (3)	0.0225 (3)	0.0002 (3)	−0.0039 (3)	−0.0032 (3)
N1	0.0174 (11)	0.0204 (9)	0.0197 (12)	−0.0007 (8)	−0.0022 (8)	−0.0024 (8)
N2	0.0199 (11)	0.0255 (11)	0.0198 (11)	0.0030 (9)	−0.0001 (9)	−0.0031 (9)
N3	0.0171 (11)	0.0236 (10)	0.0207 (12)	−0.0002 (9)	−0.0010 (9)	−0.0009 (9)
N4	0.0211 (10)	0.0234 (10)	0.0193 (12)	0.0016 (9)	0.0014 (9)	−0.0043 (9)
C1	0.0231 (13)	0.0260 (12)	0.0198 (14)	−0.0024 (10)	−0.0016 (11)	−0.0049 (10)
C2	0.0211 (12)	0.0227 (11)	0.0180 (13)	−0.0039 (9)	0.0015 (11)	−0.0014 (10)
C3	0.0163 (12)	0.0234 (12)	0.0186 (13)	−0.0019 (10)	−0.0011 (10)	0.0005 (10)
C4	0.0255 (13)	0.0203 (11)	0.0157 (13)	−0.0004 (10)	0.0031 (10)	0.0003 (9)
C5	0.0332 (15)	0.0244 (12)	0.0218 (15)	−0.0043 (12)	0.0038 (12)	−0.0016 (10)
C6	0.0455 (18)	0.0220 (13)	0.0254 (16)	−0.0022 (12)	0.0086 (14)	−0.0026 (11)
C7	0.0420 (18)	0.0276 (14)	0.0247 (16)	0.0114 (13)	0.0082 (14)	0.0017 (11)
C8	0.0266 (14)	0.0366 (14)	0.0210 (14)	0.0056 (12)	0.0026 (12)	0.0015 (12)
C9	0.0255 (13)	0.0264 (12)	0.0190 (14)	−0.0004 (11)	−0.0011 (11)	−0.0012 (11)
C10	0.0175 (12)	0.0245 (12)	0.0162 (13)	0.0034 (10)	−0.0018 (10)	−0.0051 (10)
C11	0.0204 (13)	0.0226 (12)	0.0348 (17)	0.0012 (11)	−0.0028 (11)	−0.0047 (11)
C12	0.0239 (14)	0.0354 (16)	0.0417 (19)	0.0039 (13)	−0.0080 (13)	−0.0144 (14)
C13	0.0323 (16)	0.0530 (19)	0.0234 (16)	0.0137 (15)	−0.0102 (13)	−0.0095 (14)
C14	0.0458 (19)	0.0388 (17)	0.0206 (15)	0.0114 (15)	−0.0038 (13)	0.0031 (12)
C15	0.0284 (14)	0.0272 (13)	0.0186 (14)	0.0025 (11)	0.0008 (11)	−0.0033 (10)
C16	0.0191 (12)	0.0255 (12)	0.0178 (13)	−0.0011 (10)	0.0011 (10)	0.0002 (10)
C17	0.0326 (16)	0.0433 (16)	0.0212 (16)	0.0109 (14)	−0.0024 (12)	−0.0033 (13)
C18	0.0188 (12)	0.0229 (11)	0.0167 (12)	−0.0027 (10)	0.0036 (10)	0.0001 (10)
C19	0.0259 (14)	0.0322 (14)	0.0175 (14)	0.0014 (11)	0.0009 (11)	−0.0057 (11)
C20	0.0333 (16)	0.0281 (14)	0.0256 (16)	0.0050 (12)	0.0066 (12)	−0.0080 (12)
C21	0.0289 (16)	0.0307 (14)	0.0310 (17)	0.0088 (12)	0.0025 (12)	−0.0009 (13)
C22	0.0240 (14)	0.0310 (15)	0.0245 (16)	0.0035 (12)	−0.0009 (12)	−0.0034 (11)
Br1	0.0380 (2)	0.0227 (1)	0.0221 (1)	−0.0011 (1)	−0.0049 (1)	−0.0042 (1)
O1	0.0582 (15)	0.0222 (10)	0.0257 (12)	0.0051 (9)	−0.0093 (10)	−0.0045 (8)

Geometric parameters (Å, º) top

S1—C1	1.735 (3)	C14—C15	1.393 (4)
S1—C3	1.740 (3)	C16—C18	1.469 (4)
O1—H1A	0.8400	C16—C17	1.501 (4)
O1—H1B	0.8400	C18—C19	1.394 (4)
N1—C2	1.414 (3)	C19—C20	1.394 (4)
N1—C10	1.439 (4)	C20—C21	1.375 (4)
N1—C3	1.373 (3)	C21—C22	1.374 (5)
N2—C3	1.310 (3)	C1—H1	0.9500
N2—N3	1.381 (3)	C5—H5	0.9500
N3—C16	1.293 (4)	C6—H6	0.9500
N4—C18	1.348 (3)	C7—H7	0.9500
N4—C22	1.345 (4)	C8—H8	0.9500
N4—H4	0.8900	C9—H9	0.9500
C1—C2	1.346 (4)	C11—H11	0.9500
C2—C4	1.471 (3)	C12—H12	0.9500
C4—C9	1.404 (4)	C13—H13	0.9500
C4—C5	1.401 (4)	C14—H14	0.9500
C5—C6	1.382 (4)	C15—H15	0.9500
C6—C7	1.382 (5)	C17—H17C	0.9800
C7—C8	1.389 (4)	C17—H17A	0.9800
C8—C9	1.381 (4)	C17—H17B	0.9800
C10—C11	1.393 (4)	C19—H19	0.9500
C10—C15	1.379 (4)	C20—H20	0.9500
C11—C12	1.387 (4)	C21—H21	0.9500
C12—C13	1.390 (5)	C22—H22	0.9500
C13—C14	1.369 (5)

C1—S1—C3	90.18 (12)	C19—C20—C21	119.8 (3)
H1A—O1—H1B	111.00	C20—C21—C22	119.5 (3)
C2—N1—C10	125.7 (2)	N4—C22—C21	119.5 (3)
C3—N1—C10	120.3 (2)	S1—C1—H1	123.00
C2—N1—C3	113.5 (2)	C2—C1—H1	123.00
N3—N2—C3	109.4 (2)	C6—C5—H5	120.00
N2—N3—C16	116.0 (2)	C4—C5—H5	120.00
C18—N4—C22	123.7 (2)	C5—C6—H6	120.00
C22—N4—H4	117.00	C7—C6—H6	120.00
C18—N4—H4	119.00	C8—C7—H7	120.00
S1—C1—C2	113.4 (2)	C6—C7—H7	120.00
C1—C2—C4	125.1 (2)	C9—C8—H8	120.00
N1—C2—C1	111.8 (2)	C7—C8—H8	120.00
N1—C2—C4	123.1 (2)	C4—C9—H9	120.00
N1—C3—N2	122.3 (2)	C8—C9—H9	120.00
S1—C3—N1	111.11 (18)	C10—C11—H11	121.00
S1—C3—N2	126.51 (19)	C12—C11—H11	121.00
C2—C4—C5	118.9 (2)	C13—C12—H12	120.00
C2—C4—C9	123.1 (2)	C11—C12—H12	120.00
C5—C4—C9	117.9 (2)	C12—C13—H13	120.00
C4—C5—C6	121.0 (3)	C14—C13—H13	120.00
C5—C6—C7	120.6 (3)	C15—C14—H14	120.00
C6—C7—C8	119.2 (3)	C13—C14—H14	120.00
C7—C8—C9	120.8 (3)	C10—C15—H15	120.00
C4—C9—C8	120.6 (3)	C14—C15—H15	120.00
C11—C10—C15	121.0 (3)	C16—C17—H17B	109.00
N1—C10—C11	119.5 (2)	C16—C17—H17C	109.00
N1—C10—C15	119.5 (2)	H17A—C17—H17B	109.00
C10—C11—C12	119.0 (3)	H17A—C17—H17C	109.00
C11—C12—C13	120.1 (3)	H17B—C17—H17C	110.00
C12—C13—C14	120.3 (3)	C16—C17—H17A	109.00
C13—C14—C15	120.4 (3)	C18—C19—H19	120.00
C10—C15—C14	119.2 (3)	C20—C19—H19	120.00
N3—C16—C17	126.3 (3)	C21—C20—H20	120.00
N3—C16—C18	114.8 (2)	C19—C20—H20	120.00
C17—C16—C18	118.9 (2)	C20—C21—H21	120.00
C16—C18—C19	123.5 (2)	C22—C21—H21	120.00
N4—C18—C19	117.8 (2)	N4—C22—H22	120.00
N4—C18—C16	118.8 (2)	C21—C22—H22	120.00
C18—C19—C20	119.7 (3)

C3—S1—C1—C2	0.9 (2)	C1—C2—C4—C5	33.9 (4)
C1—S1—C3—N1	−0.31 (19)	C1—C2—C4—C9	−141.5 (3)
C1—S1—C3—N2	177.4 (2)	C2—C4—C5—C6	−176.6 (3)
C3—N1—C2—C1	1.0 (3)	C9—C4—C5—C6	−1.0 (4)
C3—N1—C2—C4	−175.7 (2)	C2—C4—C9—C8	176.7 (3)
C10—N1—C2—C1	−170.8 (2)	C5—C4—C9—C8	1.3 (4)
C10—N1—C2—C4	12.5 (4)	C4—C5—C6—C7	−0.4 (5)
C2—N1—C3—S1	−0.3 (3)	C5—C6—C7—C8	1.6 (5)
C2—N1—C3—N2	−178.1 (2)	C6—C7—C8—C9	−1.3 (5)
C10—N1—C3—S1	171.96 (17)	C7—C8—C9—C4	−0.1 (4)
C10—N1—C3—N2	−5.8 (4)	N1—C10—C11—C12	−177.3 (3)
C2—N1—C10—C11	−121.3 (3)	C15—C10—C11—C12	1.7 (4)
C2—N1—C10—C15	59.7 (4)	N1—C10—C15—C14	177.9 (3)
C3—N1—C10—C11	67.5 (3)	C11—C10—C15—C14	−1.1 (4)
C3—N1—C10—C15	−111.5 (3)	C10—C11—C12—C13	−0.8 (4)
C3—N2—N3—C16	−172.8 (2)	C11—C12—C13—C14	−0.6 (5)
N3—N2—C3—S1	8.2 (3)	C12—C13—C14—C15	1.2 (5)
N3—N2—C3—N1	−174.4 (2)	C13—C14—C15—C10	−0.4 (4)
N2—N3—C16—C17	5.7 (4)	N3—C16—C18—N4	−7.6 (4)
N2—N3—C16—C18	−174.3 (2)	N3—C16—C18—C19	170.7 (3)
C22—N4—C18—C16	177.0 (3)	C17—C16—C18—N4	172.4 (2)
C22—N4—C18—C19	−1.4 (4)	C17—C16—C18—C19	−9.3 (4)
C18—N4—C22—C21	0.5 (4)	N4—C18—C19—C20	1.7 (4)
S1—C1—C2—N1	−1.2 (3)	C16—C18—C19—C20	−176.6 (3)
S1—C1—C2—C4	175.4 (2)	C18—C19—C20—C21	−1.3 (4)
N1—C2—C4—C5	−149.9 (3)	C19—C20—C21—C22	0.4 (5)
N1—C2—C4—C9	34.8 (4)	C20—C21—C22—N4	0.0 (5)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+3/2, y−3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+3/2, y−3/2, z−1/2.

Acknowledgements

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

References

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Volume 70| Part 4| April 2014| Pages o478-o479

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

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

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Experimental

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organic compounds

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