The title compound, C12H14N4O2S2·H2O, is a member of a new series of imidazo[2,1-b]thiazoles. The thiazolidine ring system adopts an envelope conformation. The packing is stabilized by intra- and intermolecular hydrogen-bond interactions.
Supporting information
CCDC reference: 270443
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.055
- wR factor = 0.178
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
N-(2,2-Dimethyl-4-oxo-1,3-thiazolidin-3-yl)-6-
methylimidazo[2,1-
b][1,3]thiazole-5-carboxamide monohydrate
top
Crystal data top
C12H14N4O2S2·H2O | F(000) = 1376 |
Mr = 328.43 | Dx = 1.390 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 19865 reflections |
a = 11.3660 (7) Å | θ = 1.6–27.6° |
b = 21.4096 (12) Å | µ = 0.35 mm−1 |
c = 12.9034 (11) Å | T = 293 K |
V = 3139.9 (4) Å3 | Prism, colorless |
Z = 8 | 0.38 × 0.35 × 0.29 mm |
Data collection top
Stoe IPDS-II diffractometer | 3558 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2155 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.038 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.5°, θmin = 2.5° |
ω scans | h = −14→14 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −27→24 |
Tmin = 0.877, Tmax = 0.904 | l = −16→15 |
19955 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.178 | w = 1/[σ2(Fo2) + (0.1017P)2 + 0.0559P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
3558 reflections | Δρmax = 0.50 e Å−3 |
214 parameters | Δρmin = −0.37 e Å−3 |
0 restraints | Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0090 (18) |
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 F2are 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 | Uiso*/Ueq | |
S1 | 1.22207 (7) | 0.54361 (4) | 0.52399 (9) | 0.0974 (4) | |
S2 | 0.46614 (8) | 0.73148 (5) | 0.37058 (8) | 0.1001 (4) | |
O1 | 0.83185 (16) | 0.63613 (11) | 0.36827 (14) | 0.0797 (8) | |
O2 | 0.5534 (2) | 0.55944 (13) | 0.3917 (2) | 0.1047 (11) | |
N1 | 1.0387 (2) | 0.58182 (13) | 0.6559 (2) | 0.0781 (9) | |
N2 | 1.01451 (18) | 0.58190 (10) | 0.48490 (18) | 0.0636 (8) | |
N3 | 0.70747 (17) | 0.62949 (12) | 0.50579 (18) | 0.0584 (7) | |
N4 | 0.61530 (16) | 0.65376 (10) | 0.44770 (17) | 0.0589 (7) | |
C1 | 0.8465 (3) | 0.6207 (2) | 0.7182 (2) | 0.0929 (13) | |
C2 | 0.9261 (2) | 0.60219 (14) | 0.6329 (2) | 0.0695 (10) | |
C3 | 1.0874 (2) | 0.57003 (13) | 0.5652 (3) | 0.0737 (10) | |
C4 | 1.1733 (3) | 0.54901 (17) | 0.3977 (4) | 0.0974 (13) | |
C5 | 1.0632 (3) | 0.56968 (16) | 0.3884 (3) | 0.0799 (11) | |
C6 | 0.9082 (2) | 0.60236 (12) | 0.5273 (2) | 0.0600 (9) | |
C7 | 0.8138 (2) | 0.62302 (13) | 0.4587 (2) | 0.0590 (9) | |
C8 | 0.5393 (2) | 0.61560 (16) | 0.4004 (2) | 0.0723 (10) | |
C9 | 0.4327 (3) | 0.6504 (2) | 0.3641 (3) | 0.0998 (14) | |
C10 | 0.5842 (2) | 0.71968 (13) | 0.4633 (2) | 0.0696 (10) | |
C11 | 0.6873 (3) | 0.76135 (18) | 0.4328 (5) | 0.1190 (19) | |
C12 | 0.5426 (4) | 0.7306 (2) | 0.5725 (3) | 0.1127 (18) | |
O3 | 0.1024 (2) | 0.54382 (12) | 0.8554 (2) | 0.0839 (9) | |
H1A | 0.79370 | 0.65250 | 0.69430 | 0.1400* | |
H1B | 0.89210 | 0.63640 | 0.77510 | 0.1400* | |
H1C | 0.80210 | 0.58500 | 0.74060 | 0.1400* | |
H3 | 0.687 (3) | 0.6018 (16) | 0.547 (3) | 0.077 (10)* | |
H4 | 1.222 (4) | 0.539 (2) | 0.339 (4) | 0.137 (16)* | |
H5 | 1.012 (3) | 0.5736 (15) | 0.331 (3) | 0.087 (10)* | |
H9A | 0.36580 | 0.64090 | 0.40800 | 0.1200* | |
H9B | 0.41350 | 0.63870 | 0.29350 | 0.1200* | |
H11A | 0.74670 | 0.75950 | 0.48550 | 0.1780* | |
H11B | 0.66040 | 0.80360 | 0.42540 | 0.1780* | |
H11C | 0.71960 | 0.74720 | 0.36810 | 0.1780* | |
H12A | 0.48120 | 0.70140 | 0.58890 | 0.1690* | |
H12B | 0.51280 | 0.77240 | 0.57870 | 0.1690* | |
H12C | 0.60700 | 0.72500 | 0.61970 | 0.1690* | |
H3A | 0.087 (4) | 0.555 (2) | 0.789 (4) | 0.122 (14)* | |
H3B | 0.056 (4) | 0.523 (2) | 0.883 (3) | 0.104 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0663 (5) | 0.0738 (6) | 0.1522 (9) | 0.0141 (3) | −0.0300 (5) | −0.0090 (5) |
S2 | 0.0811 (5) | 0.1103 (8) | 0.1090 (7) | 0.0268 (4) | −0.0198 (4) | 0.0195 (5) |
O1 | 0.0687 (11) | 0.1134 (18) | 0.0571 (12) | 0.0216 (10) | 0.0034 (8) | 0.0162 (11) |
O2 | 0.1043 (17) | 0.0817 (18) | 0.128 (2) | −0.0012 (12) | −0.0334 (15) | −0.0310 (15) |
N1 | 0.0687 (13) | 0.0805 (18) | 0.0850 (17) | −0.0165 (11) | −0.0238 (13) | 0.0267 (14) |
N2 | 0.0588 (11) | 0.0568 (13) | 0.0753 (15) | 0.0042 (9) | −0.0121 (10) | 0.0006 (10) |
N3 | 0.0539 (10) | 0.0610 (14) | 0.0603 (12) | 0.0037 (9) | −0.0057 (9) | 0.0089 (11) |
N4 | 0.0533 (10) | 0.0621 (13) | 0.0614 (12) | 0.0030 (9) | −0.0071 (8) | 0.0007 (10) |
C1 | 0.0797 (18) | 0.138 (3) | 0.0611 (17) | −0.0304 (18) | −0.0040 (14) | 0.0138 (18) |
C2 | 0.0634 (14) | 0.0762 (19) | 0.0688 (17) | −0.0175 (13) | −0.0130 (12) | 0.0165 (14) |
C3 | 0.0621 (15) | 0.0601 (18) | 0.099 (2) | −0.0084 (12) | −0.0276 (15) | 0.0139 (15) |
C4 | 0.0723 (18) | 0.083 (2) | 0.137 (3) | 0.0220 (16) | −0.005 (2) | −0.034 (2) |
C5 | 0.0697 (16) | 0.076 (2) | 0.094 (2) | 0.0166 (14) | −0.0055 (16) | −0.0195 (17) |
C6 | 0.0534 (12) | 0.0610 (16) | 0.0655 (16) | −0.0004 (10) | −0.0065 (11) | 0.0082 (12) |
C7 | 0.0559 (12) | 0.0634 (17) | 0.0576 (15) | 0.0052 (10) | −0.0038 (10) | 0.0035 (12) |
C8 | 0.0715 (16) | 0.076 (2) | 0.0694 (17) | 0.0018 (13) | −0.0170 (12) | −0.0128 (14) |
C9 | 0.0803 (19) | 0.128 (3) | 0.091 (2) | 0.0180 (19) | −0.0325 (17) | −0.027 (2) |
C10 | 0.0671 (14) | 0.0599 (17) | 0.0817 (19) | 0.0093 (12) | −0.0052 (13) | 0.0010 (13) |
C11 | 0.088 (2) | 0.068 (2) | 0.201 (5) | −0.0062 (17) | −0.010 (3) | 0.023 (3) |
C12 | 0.130 (3) | 0.123 (4) | 0.085 (2) | 0.049 (3) | −0.010 (2) | −0.028 (2) |
O3 | 0.0831 (14) | 0.0947 (17) | 0.0740 (15) | −0.0197 (12) | −0.0224 (11) | 0.0189 (12) |
Geometric parameters (Å, º) top
S1—C3 | 1.716 (3) | C2—C6 | 1.378 (4) |
S1—C4 | 1.725 (5) | C4—C5 | 1.333 (5) |
S2—C9 | 1.779 (4) | C6—C7 | 1.460 (3) |
S2—C10 | 1.815 (3) | C8—C9 | 1.498 (5) |
O1—C7 | 1.218 (3) | C10—C11 | 1.525 (5) |
O2—C8 | 1.218 (4) | C10—C12 | 1.505 (5) |
O3—H3B | 0.78 (4) | C1—H1B | 0.9600 |
O3—H3A | 0.91 (5) | C1—H1C | 0.9600 |
N1—C2 | 1.384 (3) | C1—H1A | 0.9600 |
N1—C3 | 1.319 (4) | C4—H4 | 0.96 (5) |
N2—C5 | 1.388 (4) | C5—H5 | 0.95 (4) |
N2—C6 | 1.397 (3) | C9—H9A | 0.9700 |
N2—C3 | 1.351 (4) | C9—H9B | 0.9700 |
N3—N4 | 1.389 (3) | C11—H11B | 0.9600 |
N3—C7 | 1.360 (3) | C11—H11C | 0.9600 |
N4—C8 | 1.337 (3) | C11—H11A | 0.9600 |
N4—C10 | 1.469 (3) | C12—H12C | 0.9600 |
N3—H3 | 0.83 (4) | C12—H12A | 0.9600 |
C1—C2 | 1.479 (4) | C12—H12B | 0.9600 |
| | | |
S1···C7i | 3.598 (3) | C6···C4i | 3.507 (5) |
S1···O3ii | 3.495 (3) | C6···S1i | 3.521 (3) |
S1···C6i | 3.521 (3) | C7···C11 | 3.309 (5) |
S2···C2iii | 3.590 (3) | C7···S1i | 3.598 (3) |
S2···N4 | 2.576 (2) | C7···O2 | 3.371 (3) |
S2···C1iii | 3.630 (4) | C8···O1 | 3.380 (3) |
S1···H9Aiv | 3.0400 | C9···O1xiii | 3.225 (4) |
S2···H11Aiii | 3.1200 | C11···O1 | 3.253 (5) |
O1···N2 | 2.815 (3) | C11···C7 | 3.309 (5) |
O1···N4 | 2.693 (3) | C1···H3 | 2.89 (4) |
O1···C5 | 3.001 (4) | C2···H3 | 2.94 (3) |
O1···C8 | 3.380 (3) | C2···H3Aiv | 2.90 (5) |
O1···C11 | 3.253 (5) | C3···H3Aiv | 2.91 (5) |
O1···C9v | 3.225 (4) | C3···H11Bxii | 2.8300 |
O2···O3vi | 2.871 (4) | C4···H9Aiv | 2.9500 |
O2···N3 | 2.736 (3) | C7···H5 | 2.99 (4) |
O2···C7 | 3.371 (3) | C7···H11A | 3.0400 |
O3···O2vii | 2.871 (4) | C7···H11C | 3.1000 |
O3···N1viii | 2.795 (4) | H1A···N3 | 2.6700 |
O3···N3ix | 2.828 (3) | H1A···H3 | 2.5000 |
O3···S1x | 3.495 (3) | H1B···H12Axi | 2.4600 |
O3···C1ix | 3.363 (4) | H1C···O3xi | 2.7300 |
O3···C4x | 3.278 (4) | H1C···H3Axi | 2.5600 |
O1···H5 | 2.49 (3) | H3···C2 | 2.94 (3) |
O1···H9Bv | 2.2900 | H3···H1A | 2.5000 |
O1···H11C | 2.7000 | H3···O3xi | 2.01 (4) |
O2···H3 | 2.67 (4) | H3···H3Bxi | 2.43 (6) |
O2···H3Bvi | 2.16 (4) | H3···O2 | 2.67 (4) |
O3···H4x | 2.68 (4) | H3···C1 | 2.89 (4) |
O3···H3ix | 2.01 (4) | H3A···N1viii | 1.89 (5) |
O3···H1Cix | 2.7300 | H3A···H1Cix | 2.5600 |
N1···O3iv | 2.795 (4) | H3A···C3viii | 2.91 (5) |
N1···N2 | 2.224 (3) | H3A···C2viii | 2.90 (5) |
N2···O1 | 2.815 (3) | H3B···O2vii | 2.16 (4) |
N3···C1 | 3.169 (4) | H3B···H3ix | 2.43 (6) |
N3···O3xi | 2.828 (3) | H4···O3ii | 2.68 (4) |
N3···O2 | 2.736 (3) | H5···C7 | 2.99 (4) |
N4···O1 | 2.693 (3) | H5···O1 | 2.49 (3) |
N4···S2 | 2.576 (2) | H5···H9Bv | 2.4000 |
N1···H3Aiv | 1.89 (5) | H9A···S1viii | 3.0400 |
N3···H11A | 2.8300 | H9A···C4viii | 2.9500 |
N3···H1A | 2.6700 | H9B···O1xiii | 2.2900 |
N3···H12C | 2.7700 | H9B···H5xiii | 2.4000 |
C1···O3xi | 3.363 (4) | H11A···N3 | 2.8300 |
C1···N3 | 3.169 (4) | H11A···C7 | 3.0400 |
C1···S2xii | 3.630 (4) | H11A···H12C | 2.4600 |
C2···C4i | 3.451 (5) | H11A···S2xii | 3.1200 |
C2···S2xii | 3.590 (3) | H11B···C3iii | 2.8300 |
C3···C5i | 3.498 (4) | H11C···O1 | 2.7000 |
C4···C6i | 3.507 (5) | H11C···C7 | 3.1000 |
C4···O3ii | 3.278 (4) | H12A···H1Bix | 2.4600 |
C4···C2i | 3.451 (5) | H12C···N3 | 2.7700 |
C5···O1 | 3.001 (4) | H12C···H11A | 2.4600 |
C5···C3i | 3.498 (4) | | |
| | | |
C3—S1—C4 | 89.08 (18) | S2—C10—C11 | 108.5 (3) |
C9—S2—C10 | 93.04 (15) | C11—C10—C12 | 113.1 (3) |
H3A—O3—H3B | 117 (4) | N4—C10—C11 | 110.0 (2) |
C2—N1—C3 | 105.0 (2) | S2—C10—N4 | 102.78 (17) |
C3—N2—C6 | 106.8 (2) | N4—C10—C12 | 110.7 (3) |
C5—N2—C6 | 139.1 (2) | C2—C1—H1A | 110.00 |
C3—N2—C5 | 114.1 (2) | C2—C1—H1B | 109.00 |
N4—N3—C7 | 117.9 (2) | H1A—C1—H1B | 110.00 |
N3—N4—C10 | 117.8 (2) | H1A—C1—H1C | 109.00 |
C8—N4—C10 | 119.6 (2) | C2—C1—H1C | 109.00 |
N3—N4—C8 | 120.4 (2) | H1B—C1—H1C | 109.00 |
N4—N3—H3 | 114 (2) | C5—C4—H4 | 123 (3) |
C7—N3—H3 | 118 (2) | S1—C4—H4 | 123 (3) |
N1—C2—C6 | 110.5 (2) | N2—C5—H5 | 116 (2) |
N1—C2—C1 | 119.4 (2) | C4—C5—H5 | 133 (2) |
C1—C2—C6 | 130.2 (2) | S2—C9—H9A | 110.00 |
N1—C3—N2 | 112.8 (2) | S2—C9—H9B | 110.00 |
S1—C3—N2 | 111.8 (3) | C8—C9—H9B | 110.00 |
S1—C3—N1 | 135.4 (3) | H9A—C9—H9B | 109.00 |
S1—C4—C5 | 114.1 (3) | C8—C9—H9A | 110.00 |
N2—C5—C4 | 110.9 (4) | C10—C11—H11A | 110.00 |
C2—C6—C7 | 135.2 (2) | C10—C11—H11B | 109.00 |
N2—C6—C2 | 105.0 (2) | H11A—C11—H11B | 109.00 |
N2—C6—C7 | 119.6 (2) | H11A—C11—H11C | 110.00 |
N3—C7—C6 | 114.4 (2) | C10—C11—H11C | 109.00 |
O1—C7—C6 | 121.8 (2) | H11B—C11—H11C | 109.00 |
O1—C7—N3 | 123.7 (2) | C10—C12—H12B | 109.00 |
N4—C8—C9 | 111.2 (3) | C10—C12—H12C | 110.00 |
O2—C8—N4 | 124.1 (2) | C10—C12—H12A | 109.00 |
O2—C8—C9 | 124.7 (3) | H12A—C12—H12C | 109.00 |
S2—C9—C8 | 107.3 (2) | H12B—C12—H12C | 109.00 |
S2—C10—C12 | 111.3 (2) | H12A—C12—H12B | 109.00 |
| | | |
C3—S1—C4—C5 | 0.3 (3) | C7—N3—N4—C8 | 95.4 (3) |
C4—S1—C3—N2 | −0.6 (2) | N4—N3—C7—O1 | −1.5 (4) |
C4—S1—C3—N1 | 180.0 (3) | N3—N4—C8—C9 | 166.5 (2) |
C9—S2—C10—C11 | 138.2 (3) | N3—N4—C10—C11 | 62.7 (4) |
C9—S2—C10—C12 | −96.7 (3) | N3—N4—C8—O2 | −10.9 (4) |
C9—S2—C10—N4 | 21.77 (19) | C10—N4—C8—O2 | −173.8 (3) |
C10—S2—C9—C8 | −21.1 (2) | C8—N4—C10—S2 | −18.7 (3) |
C3—N1—C2—C6 | 0.0 (3) | C10—N4—C8—C9 | 3.7 (3) |
C2—N1—C3—N2 | 0.6 (3) | N3—N4—C10—C12 | −63.0 (3) |
C3—N1—C2—C1 | −179.0 (3) | N3—N4—C10—S2 | 178.04 (17) |
C2—N1—C3—S1 | −180.0 (3) | C8—N4—C10—C11 | −134.0 (3) |
C5—N2—C3—S1 | 0.7 (3) | C8—N4—C10—C12 | 100.3 (3) |
C3—N2—C6—C7 | 175.8 (2) | N1—C2—C6—C7 | −174.3 (3) |
C6—N2—C3—N1 | −1.0 (3) | C1—C2—C6—N2 | 178.3 (3) |
C5—N2—C3—N1 | −179.8 (3) | C1—C2—C6—C7 | 4.6 (6) |
C3—N2—C5—C4 | −0.4 (4) | N1—C2—C6—N2 | −0.6 (3) |
C6—N2—C5—C4 | −178.7 (3) | S1—C4—C5—N2 | 0.0 (4) |
C6—N2—C3—S1 | 179.46 (18) | C2—C6—C7—N3 | −20.0 (5) |
C5—N2—C6—C2 | 179.2 (3) | C2—C6—C7—O1 | 156.6 (3) |
C5—N2—C6—C7 | −5.9 (5) | N2—C6—C7—N3 | 167.0 (2) |
C3—N2—C6—C2 | 0.9 (3) | N2—C6—C7—O1 | −16.4 (4) |
C7—N3—N4—C10 | −101.4 (3) | O2—C8—C9—S2 | −168.7 (2) |
N4—N3—C7—C6 | 175.0 (2) | N4—C8—C9—S2 | 13.9 (3) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+3/2, −y+1, z−1/2; (iii) x−1/2, −y+3/2, −z+1; (iv) x+1, y, z; (v) x+1/2, y, −z+1/2; (vi) −x+1/2, −y+1, z−1/2; (vii) −x+1/2, −y+1, z+1/2; (viii) x−1, y, z; (ix) x−1/2, y, −z+3/2; (x) −x+3/2, −y+1, z+1/2; (xi) x+1/2, y, −z+3/2; (xii) x+1/2, −y+3/2, −z+1; (xiii) x−1/2, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O3xi | 0.83 (4) | 2.01 (4) | 2.828 (3) | 167 (3) |
O3—H3A···N1viii | 0.91 (5) | 1.89 (5) | 2.795 (4) | 174 (4) |
O3—H3B···O2vii | 0.78 (4) | 2.16 (4) | 2.871 (4) | 152 (4) |
C5—H5···O1 | 0.95 (4) | 2.49 (3) | 3.001 (4) | 114 (3) |
C9—H9B···O1xiii | 0.97 | 2.29 | 3.225 (4) | 163 |
Symmetry codes: (vii) −x+1/2, −y+1, z+1/2; (viii) x−1, y, z; (xi) x+1/2, y, −z+3/2; (xiii) x−1/2, y, −z+1/2. |