2-((1E)-1-{2-[(2Z)-3,4-Diphenyl-2,3-di-hydro-1,3-thia-zol-2-yl-idene]hydrazin-1-yl-idene}eth-yl)pyridin-1-ium bromide monohydrate.

In the title compound, C22H19N4S(+)·Br(-)·H2O, the dihedral angles between the phenyl groups and the mean plane of the thia-zolyl-idene ring are 34.69 (13) and 64.27 (13)°, respectively, while that between the thia-zolyl-idene and pyridinium rings is 14.73 (13)°. In the crystal, zigzag chains of alternating bromide ions and water mol-ecules associate through O-H⋯Br inter-actions 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 = 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

Δρmax = 0.60 e Å−3

Δρmin = −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.

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

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

Click here for additional data file.

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

CCDC reference: 992782

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

C22H19N4S+·Br−·H2O	F(000) = 960
Mr = 469.40	Dx = 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

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

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(Fo2) + (0.0251P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.060	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.60 e Å−3
5394 reflections	Δρmin = −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)

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	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*

	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)

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)

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

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) ; (ii) ; (iii) .