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
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
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
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Data collection: APEX2 (Bruker, 2013); cell 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
10.1107/S160053681400347X/qm2104sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681400347X/qm2104Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681400347X/qm2104Isup3.cml
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).
All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with O—H = 0.85 Å, N—H = 0.88 Å, C—H = 0.95 Å and 0.98 Å, with Uiso(H) = 1.5 Uiso(C) for methyl H atoms and Uiso(H) = 1.2 Uiso(C,N,O) for other H atoms.
Data collection: APEX2 (Bruker, 2013); cell
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).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. |
C22H18BrN4S+·Br−·H2O | Z = 2 |
Mr = 548.30 | F(000) = 548 |
Triclinic, P1 | Dx = 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 |
Bruker SMART APEX CCD diffractometer | 5870 independent reflections |
Radiation source: fine-focus sealed tube | 4807 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 29.3°, θmin = 1.8° |
Absorption correction: numerical (SADABS; Bruker, 2013) | h = −7→7 |
Tmin = 0.390, Tmax = 0.760 | k = −12→12 |
20898 measured reflections | l = −30→30 |
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 | Δρmax = 0.94 e Å−3 |
272 parameters | Δρmin = −0.49 e Å−3 |
0 restraints |
C22H18BrN4S+·Br−·H2O | γ = 79.000 (1)° |
Mr = 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)° |
Bruker SMART APEX CCD diffractometer | 5870 independent reflections |
Absorption correction: numerical (SADABS; Bruker, 2013) | 4807 reflections with I > 2σ(I) |
Tmin = 0.390, Tmax = 0.760 | Rint = 0.038 |
20898 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.94 e Å−3 |
5870 reflections | Δρmin = −0.49 e Å−3 |
272 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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···Br2iv | 0.95 | 2.85 | 3.798 (3) | 175 |
C21—H21···Br2v | 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. |
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···Br2iv | 0.95 | 2.85 | 3.798 (3) | 175 |
C21—H21···Br2v | 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.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.