Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026712/hb2439sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026712/hb2439Isup2.hkl |
CCDC reference: 654874
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.007 Å
- R factor = 0.060
- wR factor = 0.156
- Data-to-parameter ratio = 20.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 2 PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.87 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.74 Ratio PLAT360_ALERT_2_B Short C(sp3)-C(sp3) Bond C17 - C18 ... 1.33 Ang.
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.73 mm PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.01 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
[6-(4-Bromophenyl)imidazo[2,1-b]thiazol-3-yl]acetic acid hydrazide (0.005 mol) and 3-pentanone (0.01 mol) were heated in 30 ml e thanol for 6 h. The precipitate obtained was purified and recrystallized from ethanol to yield colourless prisms of (I). IR [ν, cm-1, KBr]: 3177, 3116 (N—H); 1663 (C═O). 1H-NMR [δ, p.p.m., DMSO-d6]: 0.96–1.05 (6H, m, CH2CH3), 2.22–2.33 (4H, m, CH2CH3), 3.89, 4.18 (2H, 2 s, CH2CO), 7.02 (1H, s, imidazothiazole C2—H), 7.54–7.57 (2H, m, Br—Ph C3,5—H), 7.75–7.78 (2H, m, Br—Ph C2,6—H), 8.21, 8.23 (1H, 2 s, imidazothiazole C5—H), 10.35, 10.51 (1H, 2 s, CONH). APCI (+) m/z (%): 420 (MH+, 97), 419 (100), 309 (15), 279 (8), 156 (13). Analysis calculated for C18H19BrN4OS: C 51.56, H 4.57, N 13.36%. Found: C 51.48, H 4.15, N 13.50%.
The H atom bound to N3 was found from a difference Fourier map and refined freely. All C-bound H atoms were positioned geometrically, with C—H = 0.93–0.97 Å, and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(methyl C). Atoms C15 and C16 were refined isotropically.
Imidazo[2,1-b]thiazole derivatives have been reported in the literature as immunomodulatory (Hanson et al., 1991), antihelmintic (Amarouch et al., 1987), antitubercular (Ulusoy, 2002) and anticancer (Andreani et al., 1993) agents. In view of these observations, we have synthesized the title imidazo[2,1-b]thiazole derivative, (I), (Fig. 1), and we report here its crystal structure.
The thiazole and imidazole rings in (I) are essentially coplanar, with a dihedral angle of 0.7 (2)°. The benzene ring C1—C6 and the mean plane of the thiazole and imidazole rings system makes a dihedral angle of 2.99 (15)°. The values of the other geometric parameters in (I) are normal (Allen et al., 1987). The mean C—S bond length [1.737 (5) Å] in (I) may be compared with the corresponding values in similar molecules [1.7588 (2) Å (Öztürk Yıldırım, Akkurt, Ur, Cesur, Cesur & Büyükgüngör, 2005), 1.783 (2) Å (Öztürk Yıldırım, Akkurt, Ur, Cesur, Cesur & Heinemann, 2005) and 1.729 (2) Å (Akkurt et al., 2005)].
The crystal structure of (I) is stabilized by intermolecular C—H···O and N—H···O hydrogen bonding interactions (Table 1, Fig. 2).
For related literature, see: Akkurt et al. (2005); Amarouch et al. (1987); Andreani et al. (1993); Hanson et al. (1991); Allen et al. (1987) Öztürk Yıldırım, Akkurt, Ur, Cesur, Cesur & Büyükgüngör (2005); Öztürk Yıldırım, Akkurt, Ur, Cesur, Cesur & Heinemann (2005); Ulusoy (2002).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Fig. 1. View of (I), with the displacement ellipsoids for the non-H atoms drawn at the 30% probability level. | |
Fig. 2. A view of the packing and hydrogen bonding interactions for (I). |
C18H19BrN4OS | Z = 2 |
Mr = 419.34 | F(000) = 428 |
Triclinic, P1 | Dx = 1.469 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9591 (6) Å | Cell parameters from 27459 reflections |
b = 11.8636 (10) Å | θ = 2.0–28.0° |
c = 13.1247 (11) Å | µ = 2.29 mm−1 |
α = 65.411 (6)° | T = 296 K |
β = 78.892 (7)° | Prism, colourless |
γ = 75.193 (6)° | 0.73 × 0.55 × 0.45 mm |
V = 947.99 (15) Å3 |
Stoe IPDSII diffractometer | 4441 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3359 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.082 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.8°, θmin = 2.0° |
ω scans | h = −9→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −15→15 |
Tmin = 0.285, Tmax = 0.425 | l = −17→17 |
17037 measured reflections |
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)] = 0.061 | Hydrogen site location: difmap and geom |
wR(F2) = 0.157 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0637P)2 + 1.3183P] where P = (Fo2 + 2Fc2)/3 |
4441 reflections | (Δ/σ)max < 0.001 |
222 parameters | Δρmax = 1.18 e Å−3 |
0 restraints | Δρmin = −0.59 e Å−3 |
C18H19BrN4OS | γ = 75.193 (6)° |
Mr = 419.34 | V = 947.99 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.9591 (6) Å | Mo Kα radiation |
b = 11.8636 (10) Å | µ = 2.29 mm−1 |
c = 13.1247 (11) Å | T = 296 K |
α = 65.411 (6)° | 0.73 × 0.55 × 0.45 mm |
β = 78.892 (7)° |
Stoe IPDSII diffractometer | 4441 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 3359 reflections with I > 2σ(I) |
Tmin = 0.285, Tmax = 0.425 | Rint = 0.082 |
17037 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.157 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 1.18 e Å−3 |
4441 reflections | Δρmin = −0.59 e Å−3 |
222 parameters |
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 | 0.34386 (10) | 0.34838 (5) | 0.62926 (5) | 0.0877 (3) | |
S1 | −0.38374 (15) | 0.10794 (12) | 0.20860 (10) | 0.0661 (4) | |
O1 | 0.2946 (4) | 0.0228 (2) | 0.0805 (2) | 0.0620 (9) | |
N1 | −0.1843 (4) | 0.1789 (3) | 0.3338 (3) | 0.0514 (10) | |
N2 | −0.0323 (4) | 0.0263 (3) | 0.2714 (2) | 0.0409 (8) | |
N3 | 0.4446 (5) | −0.1704 (3) | 0.0873 (3) | 0.0476 (9) | |
N4 | 0.4402 (5) | −0.2985 (3) | 0.1318 (3) | 0.0499 (9) | |
C1 | 0.2832 (6) | 0.1406 (4) | 0.4558 (3) | 0.0526 (12) | |
C2 | 0.3607 (6) | 0.1905 (4) | 0.5137 (3) | 0.0576 (12) | |
C3 | 0.2373 (7) | 0.2826 (4) | 0.5476 (3) | 0.0553 (14) | |
C4 | 0.0423 (7) | 0.3269 (4) | 0.5226 (3) | 0.0569 (14) | |
C5 | −0.0317 (6) | 0.2779 (4) | 0.4628 (3) | 0.0528 (12) | |
C6 | 0.0875 (5) | 0.1840 (3) | 0.4283 (3) | 0.0429 (10) | |
C7 | 0.0093 (5) | 0.1322 (3) | 0.3645 (3) | 0.0416 (10) | |
C8 | −0.2005 (5) | 0.1129 (4) | 0.2781 (3) | 0.0472 (11) | |
C9 | −0.2219 (6) | −0.0128 (4) | 0.1743 (3) | 0.0556 (12) | |
C10 | −0.0436 (5) | −0.0466 (3) | 0.2131 (3) | 0.0442 (10) | |
C11 | 0.1039 (5) | 0.0386 (3) | 0.3270 (3) | 0.0427 (10) | |
C12 | 0.1278 (5) | −0.1464 (3) | 0.2006 (3) | 0.0488 (11) | |
C13 | 0.2949 (5) | −0.0909 (3) | 0.1179 (3) | 0.0432 (10) | |
C14 | 0.5868 (7) | −0.3734 (4) | 0.1055 (4) | 0.0713 (16) | |
C15 | 0.5786 (9) | −0.5109 (4) | 0.1570 (5) | 0.091 (2) | |
C16 | 0.4022 (11) | −0.5455 (5) | 0.2333 (7) | 0.117 (3) | |
C17 | 0.7561 (11) | −0.3342 (7) | 0.0056 (6) | 0.114 (2)* | |
C18 | 0.8921 (15) | −0.3345 (10) | 0.0640 (9) | 0.161 (4)* | |
H1 | 0.36400 | 0.07660 | 0.43480 | 0.0630* | |
HN3 | 0.533 (6) | −0.136 (4) | 0.042 (4) | 0.055 (12)* | |
H2 | 0.49330 | 0.16260 | 0.52940 | 0.0690* | |
H4 | −0.03900 | 0.38920 | 0.54570 | 0.0680* | |
H5 | −0.16330 | 0.30820 | 0.44530 | 0.0630* | |
H9 | −0.25680 | −0.05030 | 0.13260 | 0.0670* | |
H11 | 0.23370 | −0.00730 | 0.33710 | 0.0510* | |
H12A | 0.08230 | −0.20020 | 0.17520 | 0.0590* | |
H12B | 0.17780 | −0.19850 | 0.27330 | 0.0590* | |
H15A | 0.58810 | −0.53950 | 0.09660 | 0.1100* | |
H15B | 0.69530 | −0.55650 | 0.19780 | 0.1100* | |
H16A | 0.39700 | −0.52500 | 0.29740 | 0.1750* | |
H16B | 0.40870 | −0.63460 | 0.25790 | 0.1750* | |
H16C | 0.28470 | −0.49970 | 0.19490 | 0.1750* | |
H17A | 0.80230 | −0.39590 | −0.02880 | 0.1370* | |
H17B | 0.71370 | −0.25130 | −0.05160 | 0.1370* | |
H18A | 0.84180 | −0.27110 | 0.09520 | 0.2420* | |
H18B | 1.01190 | −0.31650 | 0.01530 | 0.2420* | |
H18C | 0.92100 | −0.41600 | 0.12380 | 0.2420* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1192 (5) | 0.0840 (4) | 0.0870 (4) | −0.0292 (3) | −0.0284 (3) | −0.0463 (3) |
S1 | 0.0437 (5) | 0.0868 (8) | 0.0774 (7) | 0.0001 (5) | −0.0194 (5) | −0.0427 (6) |
O1 | 0.0670 (17) | 0.0415 (14) | 0.0719 (18) | −0.0176 (12) | 0.0251 (14) | −0.0262 (13) |
N1 | 0.0413 (16) | 0.0578 (18) | 0.0576 (18) | −0.0008 (13) | −0.0073 (13) | −0.0290 (15) |
N2 | 0.0345 (13) | 0.0475 (15) | 0.0421 (14) | −0.0089 (11) | −0.0011 (11) | −0.0194 (12) |
N3 | 0.0515 (17) | 0.0403 (15) | 0.0472 (16) | −0.0131 (13) | 0.0056 (13) | −0.0154 (13) |
N4 | 0.0593 (18) | 0.0383 (15) | 0.0482 (16) | −0.0082 (13) | −0.0050 (13) | −0.0139 (13) |
C1 | 0.057 (2) | 0.053 (2) | 0.050 (2) | −0.0034 (17) | −0.0100 (16) | −0.0244 (17) |
C2 | 0.060 (2) | 0.060 (2) | 0.056 (2) | −0.0087 (18) | −0.0158 (18) | −0.0231 (19) |
C3 | 0.079 (3) | 0.049 (2) | 0.0434 (19) | −0.0227 (19) | −0.0082 (18) | −0.0165 (16) |
C4 | 0.070 (3) | 0.047 (2) | 0.058 (2) | −0.0144 (18) | 0.0023 (19) | −0.0265 (18) |
C5 | 0.052 (2) | 0.050 (2) | 0.058 (2) | −0.0094 (16) | −0.0015 (16) | −0.0244 (18) |
C6 | 0.0467 (18) | 0.0420 (17) | 0.0378 (16) | −0.0112 (14) | −0.0008 (13) | −0.0134 (14) |
C7 | 0.0406 (17) | 0.0428 (17) | 0.0407 (16) | −0.0071 (13) | −0.0032 (13) | −0.0166 (14) |
C8 | 0.0366 (16) | 0.054 (2) | 0.0498 (19) | −0.0031 (14) | −0.0070 (14) | −0.0212 (16) |
C9 | 0.052 (2) | 0.070 (2) | 0.055 (2) | −0.0175 (18) | −0.0051 (16) | −0.0309 (19) |
C10 | 0.0454 (18) | 0.0487 (18) | 0.0417 (17) | −0.0173 (14) | 0.0030 (14) | −0.0191 (15) |
C11 | 0.0352 (16) | 0.0476 (18) | 0.0459 (17) | −0.0063 (13) | −0.0070 (13) | −0.0183 (15) |
C12 | 0.052 (2) | 0.0473 (19) | 0.0501 (19) | −0.0181 (16) | 0.0071 (15) | −0.0220 (16) |
C13 | 0.0479 (18) | 0.0423 (18) | 0.0412 (16) | −0.0112 (14) | 0.0030 (14) | −0.0197 (14) |
C14 | 0.074 (3) | 0.044 (2) | 0.080 (3) | −0.004 (2) | 0.009 (2) | −0.020 (2) |
C15 | 0.112 (4) | 0.038 (2) | 0.104 (4) | −0.002 (2) | −0.001 (3) | −0.020 (2) |
C16 | 0.128 (5) | 0.044 (3) | 0.144 (6) | −0.024 (3) | 0.019 (5) | −0.013 (3) |
Br1—C3 | 1.899 (5) | C12—C13 | 1.508 (5) |
S1—C8 | 1.730 (4) | C14—C15 | 1.495 (7) |
S1—C9 | 1.744 (5) | C14—C17 | 1.581 (9) |
O1—C13 | 1.228 (4) | C15—C16 | 1.456 (10) |
N1—C7 | 1.388 (5) | C17—C18 | 1.326 (14) |
N1—C8 | 1.309 (6) | C1—H1 | 0.9300 |
N2—C8 | 1.362 (6) | C2—H2 | 0.9300 |
N2—C10 | 1.396 (5) | C4—H4 | 0.9300 |
N2—C11 | 1.370 (5) | C5—H5 | 0.9300 |
N3—N4 | 1.389 (5) | C9—H9 | 0.9300 |
N3—C13 | 1.337 (5) | C11—H11 | 0.9300 |
N4—C14 | 1.267 (6) | C12—H12A | 0.9700 |
N3—HN3 | 0.83 (5) | C12—H12B | 0.9700 |
C1—C6 | 1.388 (6) | C15—H15A | 0.9700 |
C1—C2 | 1.384 (6) | C15—H15B | 0.9700 |
C2—C3 | 1.381 (7) | C16—H16A | 0.9600 |
C3—C4 | 1.374 (7) | C16—H16B | 0.9600 |
C4—C5 | 1.381 (6) | C16—H16C | 0.9600 |
C5—C6 | 1.392 (6) | C17—H17A | 0.9700 |
C6—C7 | 1.466 (5) | C17—H17B | 0.9700 |
C7—C11 | 1.366 (5) | C18—H18A | 0.9600 |
C9—C10 | 1.334 (6) | C18—H18B | 0.9600 |
C10—C12 | 1.489 (5) | C18—H18C | 0.9600 |
C8—S1—C9 | 89.5 (2) | C2—C1—H1 | 119.00 |
C7—N1—C8 | 103.6 (3) | C6—C1—H1 | 119.00 |
C8—N2—C10 | 115.3 (3) | C1—C2—H2 | 121.00 |
C8—N2—C11 | 106.2 (3) | C3—C2—H2 | 121.00 |
C10—N2—C11 | 138.4 (3) | C3—C4—H4 | 120.00 |
N4—N3—C13 | 119.5 (3) | C5—C4—H4 | 120.00 |
N3—N4—C14 | 118.8 (4) | C4—C5—H5 | 119.00 |
C13—N3—HN3 | 114 (3) | C6—C5—H5 | 119.00 |
N4—N3—HN3 | 126 (3) | S1—C9—H9 | 123.00 |
C2—C1—C6 | 121.5 (4) | C10—C9—H9 | 123.00 |
C1—C2—C3 | 118.7 (4) | N2—C11—H11 | 127.00 |
Br1—C3—C4 | 120.3 (4) | C7—C11—H11 | 127.00 |
C2—C3—C4 | 121.3 (4) | C10—C12—H12A | 109.00 |
Br1—C3—C2 | 118.4 (4) | C10—C12—H12B | 109.00 |
C3—C4—C5 | 119.3 (4) | C13—C12—H12A | 109.00 |
C4—C5—C6 | 121.1 (4) | C13—C12—H12B | 109.00 |
C1—C6—C5 | 118.2 (4) | H12A—C12—H12B | 108.00 |
C5—C6—C7 | 121.1 (3) | C14—C15—H15A | 108.00 |
C1—C6—C7 | 120.7 (4) | C14—C15—H15B | 108.00 |
N1—C7—C11 | 111.0 (3) | C16—C15—H15A | 108.00 |
N1—C7—C6 | 120.6 (3) | C16—C15—H15B | 108.00 |
C6—C7—C11 | 128.5 (3) | H15A—C15—H15B | 107.00 |
S1—C8—N2 | 110.6 (3) | C15—C16—H16A | 109.00 |
S1—C8—N1 | 136.0 (3) | C15—C16—H16B | 109.00 |
N1—C8—N2 | 113.5 (3) | C15—C16—H16C | 109.00 |
S1—C9—C10 | 114.0 (3) | H16A—C16—H16B | 109.00 |
N2—C10—C12 | 121.3 (3) | H16A—C16—H16C | 110.00 |
C9—C10—C12 | 128.2 (4) | H16B—C16—H16C | 109.00 |
N2—C10—C9 | 110.5 (3) | C14—C17—H17A | 112.00 |
N2—C11—C7 | 105.7 (3) | C14—C17—H17B | 112.00 |
C10—C12—C13 | 111.9 (3) | C18—C17—H17A | 112.00 |
O1—C13—N3 | 121.1 (3) | C18—C17—H17B | 112.00 |
N3—C13—C12 | 117.5 (3) | H17A—C17—H17B | 110.00 |
O1—C13—C12 | 121.4 (3) | C17—C18—H18A | 109.00 |
N4—C14—C17 | 126.0 (5) | C17—C18—H18B | 109.00 |
N4—C14—C15 | 117.2 (5) | C17—C18—H18C | 109.00 |
C15—C14—C17 | 115.6 (5) | H18A—C18—H18B | 109.00 |
C14—C15—C16 | 116.4 (5) | H18A—C18—H18C | 109.00 |
C14—C17—C18 | 98.4 (7) | H18B—C18—H18C | 109.00 |
C8—S1—C9—C10 | 0.2 (3) | C6—C1—C2—C3 | 2.1 (6) |
C9—S1—C8—N1 | 179.7 (4) | C1—C2—C3—Br1 | 178.9 (3) |
C9—S1—C8—N2 | 0.3 (3) | C1—C2—C3—C4 | −1.5 (6) |
C8—N1—C7—C6 | 179.2 (3) | Br1—C3—C4—C5 | 179.8 (3) |
C8—N1—C7—C11 | −0.4 (4) | C2—C3—C4—C5 | 0.3 (6) |
C7—N1—C8—S1 | −178.9 (4) | C3—C4—C5—C6 | 0.5 (6) |
C7—N1—C8—N2 | 0.5 (4) | C4—C5—C6—C7 | −179.8 (4) |
C11—N2—C10—C12 | 1.2 (6) | C4—C5—C6—C1 | 0.1 (6) |
C10—N2—C8—S1 | −0.7 (4) | C1—C6—C7—N1 | −177.8 (4) |
C10—N2—C8—N1 | 179.7 (3) | C5—C6—C7—C11 | −178.3 (4) |
C8—N2—C11—C7 | 0.2 (4) | C1—C6—C7—C11 | 1.8 (6) |
C11—N2—C8—N1 | −0.5 (4) | C5—C6—C7—N1 | 2.1 (5) |
C11—N2—C8—S1 | 179.2 (2) | N1—C7—C11—N2 | 0.2 (4) |
C8—N2—C10—C12 | −179.0 (3) | C6—C7—C11—N2 | −179.5 (3) |
C10—N2—C11—C7 | 180.0 (4) | S1—C9—C10—C12 | 179.2 (3) |
C11—N2—C10—C9 | −178.9 (4) | S1—C9—C10—N2 | −0.7 (4) |
C8—N2—C10—C9 | 0.9 (4) | N2—C10—C12—C13 | −73.2 (4) |
N4—N3—C13—O1 | 179.7 (3) | C9—C10—C12—C13 | 106.9 (4) |
N4—N3—C13—C12 | 0.2 (5) | C10—C12—C13—O1 | 9.8 (5) |
C13—N3—N4—C14 | −177.3 (4) | C10—C12—C13—N3 | −170.7 (3) |
N3—N4—C14—C15 | 178.7 (4) | N4—C14—C15—C16 | −0.3 (8) |
N3—N4—C14—C17 | −14.5 (7) | C17—C14—C15—C16 | −168.4 (6) |
C2—C1—C6—C7 | 178.5 (4) | N4—C14—C17—C18 | 96.4 (8) |
C2—C1—C6—C5 | −1.4 (6) | C15—C14—C17—C18 | −96.7 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—HN3···O1i | 0.83 (5) | 2.03 (5) | 2.844 (4) | 169 (4) |
C17—H17B···O1i | 0.97 | 2.56 | 3.326 (9) | 136 |
Symmetry code: (i) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C18H19BrN4OS |
Mr | 419.34 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 6.9591 (6), 11.8636 (10), 13.1247 (11) |
α, β, γ (°) | 65.411 (6), 78.892 (7), 75.193 (6) |
V (Å3) | 947.99 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.29 |
Crystal size (mm) | 0.73 × 0.55 × 0.45 |
Data collection | |
Diffractometer | Stoe IPDSII |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.285, 0.425 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17037, 4441, 3359 |
Rint | 0.082 |
(sin θ/λ)max (Å−1) | 0.655 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.157, 1.02 |
No. of reflections | 4441 |
No. of parameters | 222 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.18, −0.59 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—HN3···O1i | 0.83 (5) | 2.03 (5) | 2.844 (4) | 169 (4) |
C17—H17B···O1i | 0.97 | 2.56 | 3.326 (9) | 136 |
Symmetry code: (i) −x+1, −y, −z. |
Imidazo[2,1-b]thiazole derivatives have been reported in the literature as immunomodulatory (Hanson et al., 1991), antihelmintic (Amarouch et al., 1987), antitubercular (Ulusoy, 2002) and anticancer (Andreani et al., 1993) agents. In view of these observations, we have synthesized the title imidazo[2,1-b]thiazole derivative, (I), (Fig. 1), and we report here its crystal structure.
The thiazole and imidazole rings in (I) are essentially coplanar, with a dihedral angle of 0.7 (2)°. The benzene ring C1—C6 and the mean plane of the thiazole and imidazole rings system makes a dihedral angle of 2.99 (15)°. The values of the other geometric parameters in (I) are normal (Allen et al., 1987). The mean C—S bond length [1.737 (5) Å] in (I) may be compared with the corresponding values in similar molecules [1.7588 (2) Å (Öztürk Yıldırım, Akkurt, Ur, Cesur, Cesur & Büyükgüngör, 2005), 1.783 (2) Å (Öztürk Yıldırım, Akkurt, Ur, Cesur, Cesur & Heinemann, 2005) and 1.729 (2) Å (Akkurt et al., 2005)].
The crystal structure of (I) is stabilized by intermolecular C—H···O and N—H···O hydrogen bonding interactions (Table 1, Fig. 2).