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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006525/hg6147sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006525/hg61473sup2.hkl
Contains datablock 3

CCDC reference: 270443

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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·H2OF(000) = 1376
Mr = 328.43Dx = 1.390 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 19865 reflections
a = 11.3660 (7) Åθ = 1.6–27.6°
b = 21.4096 (12) ŵ = 0.35 mm1
c = 12.9034 (11) ÅT = 293 K
V = 3139.9 (4) Å3Prism, colorless
Z = 80.38 × 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 focus2155 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.038
Detector resolution: 6.67 pixels mm-1θmax = 27.5°, θmin = 2.5°
ω scansh = 1414
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 2724
Tmin = 0.877, Tmax = 0.904l = 1615
19955 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H 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 reflectionsΔρmax = 0.50 e Å3
214 parametersΔρmin = 0.37 e Å3
0 restraintsExtinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
S11.22207 (7)0.54361 (4)0.52399 (9)0.0974 (4)
S20.46614 (8)0.73148 (5)0.37058 (8)0.1001 (4)
O10.83185 (16)0.63613 (11)0.36827 (14)0.0797 (8)
O20.5534 (2)0.55944 (13)0.3917 (2)0.1047 (11)
N11.0387 (2)0.58182 (13)0.6559 (2)0.0781 (9)
N21.01451 (18)0.58190 (10)0.48490 (18)0.0636 (8)
N30.70747 (17)0.62949 (12)0.50579 (18)0.0584 (7)
N40.61530 (16)0.65376 (10)0.44770 (17)0.0589 (7)
C10.8465 (3)0.6207 (2)0.7182 (2)0.0929 (13)
C20.9261 (2)0.60219 (14)0.6329 (2)0.0695 (10)
C31.0874 (2)0.57003 (13)0.5652 (3)0.0737 (10)
C41.1733 (3)0.54901 (17)0.3977 (4)0.0974 (13)
C51.0632 (3)0.56968 (16)0.3884 (3)0.0799 (11)
C60.9082 (2)0.60236 (12)0.5273 (2)0.0600 (9)
C70.8138 (2)0.62302 (13)0.4587 (2)0.0590 (9)
C80.5393 (2)0.61560 (16)0.4004 (2)0.0723 (10)
C90.4327 (3)0.6504 (2)0.3641 (3)0.0998 (14)
C100.5842 (2)0.71968 (13)0.4633 (2)0.0696 (10)
C110.6873 (3)0.76135 (18)0.4328 (5)0.1190 (19)
C120.5426 (4)0.7306 (2)0.5725 (3)0.1127 (18)
O30.1024 (2)0.54382 (12)0.8554 (2)0.0839 (9)
H1A0.793700.652500.694300.1400*
H1B0.892100.636400.775100.1400*
H1C0.802100.585000.740600.1400*
H30.687 (3)0.6018 (16)0.547 (3)0.077 (10)*
H41.222 (4)0.539 (2)0.339 (4)0.137 (16)*
H51.012 (3)0.5736 (15)0.331 (3)0.087 (10)*
H9A0.365800.640900.408000.1200*
H9B0.413500.638700.293500.1200*
H11A0.746700.759500.485500.1780*
H11B0.660400.803600.425400.1780*
H11C0.719600.747200.368100.1780*
H12A0.481200.701400.588900.1690*
H12B0.512800.772400.578700.1690*
H12C0.607000.725000.619700.1690*
H3A0.087 (4)0.555 (2)0.789 (4)0.122 (14)*
H3B0.056 (4)0.523 (2)0.883 (3)0.104 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0663 (5)0.0738 (6)0.1522 (9)0.0141 (3)0.0300 (5)0.0090 (5)
S20.0811 (5)0.1103 (8)0.1090 (7)0.0268 (4)0.0198 (4)0.0195 (5)
O10.0687 (11)0.1134 (18)0.0571 (12)0.0216 (10)0.0034 (8)0.0162 (11)
O20.1043 (17)0.0817 (18)0.128 (2)0.0012 (12)0.0334 (15)0.0310 (15)
N10.0687 (13)0.0805 (18)0.0850 (17)0.0165 (11)0.0238 (13)0.0267 (14)
N20.0588 (11)0.0568 (13)0.0753 (15)0.0042 (9)0.0121 (10)0.0006 (10)
N30.0539 (10)0.0610 (14)0.0603 (12)0.0037 (9)0.0057 (9)0.0089 (11)
N40.0533 (10)0.0621 (13)0.0614 (12)0.0030 (9)0.0071 (8)0.0007 (10)
C10.0797 (18)0.138 (3)0.0611 (17)0.0304 (18)0.0040 (14)0.0138 (18)
C20.0634 (14)0.0762 (19)0.0688 (17)0.0175 (13)0.0130 (12)0.0165 (14)
C30.0621 (15)0.0601 (18)0.099 (2)0.0084 (12)0.0276 (15)0.0139 (15)
C40.0723 (18)0.083 (2)0.137 (3)0.0220 (16)0.005 (2)0.034 (2)
C50.0697 (16)0.076 (2)0.094 (2)0.0166 (14)0.0055 (16)0.0195 (17)
C60.0534 (12)0.0610 (16)0.0655 (16)0.0004 (10)0.0065 (11)0.0082 (12)
C70.0559 (12)0.0634 (17)0.0576 (15)0.0052 (10)0.0038 (10)0.0035 (12)
C80.0715 (16)0.076 (2)0.0694 (17)0.0018 (13)0.0170 (12)0.0128 (14)
C90.0803 (19)0.128 (3)0.091 (2)0.0180 (19)0.0325 (17)0.027 (2)
C100.0671 (14)0.0599 (17)0.0817 (19)0.0093 (12)0.0052 (13)0.0010 (13)
C110.088 (2)0.068 (2)0.201 (5)0.0062 (17)0.010 (3)0.023 (3)
C120.130 (3)0.123 (4)0.085 (2)0.049 (3)0.010 (2)0.028 (2)
O30.0831 (14)0.0947 (17)0.0740 (15)0.0197 (12)0.0224 (11)0.0189 (12)
Geometric parameters (Å, º) top
S1—C31.716 (3)C2—C61.378 (4)
S1—C41.725 (5)C4—C51.333 (5)
S2—C91.779 (4)C6—C71.460 (3)
S2—C101.815 (3)C8—C91.498 (5)
O1—C71.218 (3)C10—C111.525 (5)
O2—C81.218 (4)C10—C121.505 (5)
O3—H3B0.78 (4)C1—H1B0.9600
O3—H3A0.91 (5)C1—H1C0.9600
N1—C21.384 (3)C1—H1A0.9600
N1—C31.319 (4)C4—H40.96 (5)
N2—C51.388 (4)C5—H50.95 (4)
N2—C61.397 (3)C9—H9A0.9700
N2—C31.351 (4)C9—H9B0.9700
N3—N41.389 (3)C11—H11B0.9600
N3—C71.360 (3)C11—H11C0.9600
N4—C81.337 (3)C11—H11A0.9600
N4—C101.469 (3)C12—H12C0.9600
N3—H30.83 (4)C12—H12A0.9600
C1—C21.479 (4)C12—H12B0.9600
S1···C7i3.598 (3)C6···C4i3.507 (5)
S1···O3ii3.495 (3)C6···S1i3.521 (3)
S1···C6i3.521 (3)C7···C113.309 (5)
S2···C2iii3.590 (3)C7···S1i3.598 (3)
S2···N42.576 (2)C7···O23.371 (3)
S2···C1iii3.630 (4)C8···O13.380 (3)
S1···H9Aiv3.0400C9···O1xiii3.225 (4)
S2···H11Aiii3.1200C11···O13.253 (5)
O1···N22.815 (3)C11···C73.309 (5)
O1···N42.693 (3)C1···H32.89 (4)
O1···C53.001 (4)C2···H32.94 (3)
O1···C83.380 (3)C2···H3Aiv2.90 (5)
O1···C113.253 (5)C3···H3Aiv2.91 (5)
O1···C9v3.225 (4)C3···H11Bxii2.8300
O2···O3vi2.871 (4)C4···H9Aiv2.9500
O2···N32.736 (3)C7···H52.99 (4)
O2···C73.371 (3)C7···H11A3.0400
O3···O2vii2.871 (4)C7···H11C3.1000
O3···N1viii2.795 (4)H1A···N32.6700
O3···N3ix2.828 (3)H1A···H32.5000
O3···S1x3.495 (3)H1B···H12Axi2.4600
O3···C1ix3.363 (4)H1C···O3xi2.7300
O3···C4x3.278 (4)H1C···H3Axi2.5600
O1···H52.49 (3)H3···C22.94 (3)
O1···H9Bv2.2900H3···H1A2.5000
O1···H11C2.7000H3···O3xi2.01 (4)
O2···H32.67 (4)H3···H3Bxi2.43 (6)
O2···H3Bvi2.16 (4)H3···O22.67 (4)
O3···H4x2.68 (4)H3···C12.89 (4)
O3···H3ix2.01 (4)H3A···N1viii1.89 (5)
O3···H1Cix2.7300H3A···H1Cix2.5600
N1···O3iv2.795 (4)H3A···C3viii2.91 (5)
N1···N22.224 (3)H3A···C2viii2.90 (5)
N2···O12.815 (3)H3B···O2vii2.16 (4)
N3···C13.169 (4)H3B···H3ix2.43 (6)
N3···O3xi2.828 (3)H4···O3ii2.68 (4)
N3···O22.736 (3)H5···C72.99 (4)
N4···O12.693 (3)H5···O12.49 (3)
N4···S22.576 (2)H5···H9Bv2.4000
N1···H3Aiv1.89 (5)H9A···S1viii3.0400
N3···H11A2.8300H9A···C4viii2.9500
N3···H1A2.6700H9B···O1xiii2.2900
N3···H12C2.7700H9B···H5xiii2.4000
C1···O3xi3.363 (4)H11A···N32.8300
C1···N33.169 (4)H11A···C73.0400
C1···S2xii3.630 (4)H11A···H12C2.4600
C2···C4i3.451 (5)H11A···S2xii3.1200
C2···S2xii3.590 (3)H11B···C3iii2.8300
C3···C5i3.498 (4)H11C···O12.7000
C4···C6i3.507 (5)H11C···C73.1000
C4···O3ii3.278 (4)H12A···H1Bix2.4600
C4···C2i3.451 (5)H12C···N32.7700
C5···O13.001 (4)H12C···H11A2.4600
C5···C3i3.498 (4)
C3—S1—C489.08 (18)S2—C10—C11108.5 (3)
C9—S2—C1093.04 (15)C11—C10—C12113.1 (3)
H3A—O3—H3B117 (4)N4—C10—C11110.0 (2)
C2—N1—C3105.0 (2)S2—C10—N4102.78 (17)
C3—N2—C6106.8 (2)N4—C10—C12110.7 (3)
C5—N2—C6139.1 (2)C2—C1—H1A110.00
C3—N2—C5114.1 (2)C2—C1—H1B109.00
N4—N3—C7117.9 (2)H1A—C1—H1B110.00
N3—N4—C10117.8 (2)H1A—C1—H1C109.00
C8—N4—C10119.6 (2)C2—C1—H1C109.00
N3—N4—C8120.4 (2)H1B—C1—H1C109.00
N4—N3—H3114 (2)C5—C4—H4123 (3)
C7—N3—H3118 (2)S1—C4—H4123 (3)
N1—C2—C6110.5 (2)N2—C5—H5116 (2)
N1—C2—C1119.4 (2)C4—C5—H5133 (2)
C1—C2—C6130.2 (2)S2—C9—H9A110.00
N1—C3—N2112.8 (2)S2—C9—H9B110.00
S1—C3—N2111.8 (3)C8—C9—H9B110.00
S1—C3—N1135.4 (3)H9A—C9—H9B109.00
S1—C4—C5114.1 (3)C8—C9—H9A110.00
N2—C5—C4110.9 (4)C10—C11—H11A110.00
C2—C6—C7135.2 (2)C10—C11—H11B109.00
N2—C6—C2105.0 (2)H11A—C11—H11B109.00
N2—C6—C7119.6 (2)H11A—C11—H11C110.00
N3—C7—C6114.4 (2)C10—C11—H11C109.00
O1—C7—C6121.8 (2)H11B—C11—H11C109.00
O1—C7—N3123.7 (2)C10—C12—H12B109.00
N4—C8—C9111.2 (3)C10—C12—H12C110.00
O2—C8—N4124.1 (2)C10—C12—H12A109.00
O2—C8—C9124.7 (3)H12A—C12—H12C109.00
S2—C9—C8107.3 (2)H12B—C12—H12C109.00
S2—C10—C12111.3 (2)H12A—C12—H12B109.00
C3—S1—C4—C50.3 (3)C7—N3—N4—C895.4 (3)
C4—S1—C3—N20.6 (2)N4—N3—C7—O11.5 (4)
C4—S1—C3—N1180.0 (3)N3—N4—C8—C9166.5 (2)
C9—S2—C10—C11138.2 (3)N3—N4—C10—C1162.7 (4)
C9—S2—C10—C1296.7 (3)N3—N4—C8—O210.9 (4)
C9—S2—C10—N421.77 (19)C10—N4—C8—O2173.8 (3)
C10—S2—C9—C821.1 (2)C8—N4—C10—S218.7 (3)
C3—N1—C2—C60.0 (3)C10—N4—C8—C93.7 (3)
C2—N1—C3—N20.6 (3)N3—N4—C10—C1263.0 (3)
C3—N1—C2—C1179.0 (3)N3—N4—C10—S2178.04 (17)
C2—N1—C3—S1180.0 (3)C8—N4—C10—C11134.0 (3)
C5—N2—C3—S10.7 (3)C8—N4—C10—C12100.3 (3)
C3—N2—C6—C7175.8 (2)N1—C2—C6—C7174.3 (3)
C6—N2—C3—N11.0 (3)C1—C2—C6—N2178.3 (3)
C5—N2—C3—N1179.8 (3)C1—C2—C6—C74.6 (6)
C3—N2—C5—C40.4 (4)N1—C2—C6—N20.6 (3)
C6—N2—C5—C4178.7 (3)S1—C4—C5—N20.0 (4)
C6—N2—C3—S1179.46 (18)C2—C6—C7—N320.0 (5)
C5—N2—C6—C2179.2 (3)C2—C6—C7—O1156.6 (3)
C5—N2—C6—C75.9 (5)N2—C6—C7—N3167.0 (2)
C3—N2—C6—C20.9 (3)N2—C6—C7—O116.4 (4)
C7—N3—N4—C10101.4 (3)O2—C8—C9—S2168.7 (2)
N4—N3—C7—C6175.0 (2)N4—C8—C9—S213.9 (3)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+3/2, y+1, z1/2; (iii) x1/2, y+3/2, z+1; (iv) x+1, y, z; (v) x+1/2, y, z+1/2; (vi) x+1/2, y+1, z1/2; (vii) x+1/2, y+1, z+1/2; (viii) x1, y, z; (ix) x1/2, 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) x1/2, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O3xi0.83 (4)2.01 (4)2.828 (3)167 (3)
O3—H3A···N1viii0.91 (5)1.89 (5)2.795 (4)174 (4)
O3—H3B···O2vii0.78 (4)2.16 (4)2.871 (4)152 (4)
C5—H5···O10.95 (4)2.49 (3)3.001 (4)114 (3)
C9—H9B···O1xiii0.972.293.225 (4)163
Symmetry codes: (vii) x+1/2, y+1, z+1/2; (viii) x1, y, z; (xi) x+1/2, y, z+3/2; (xiii) x1/2, y, z+1/2.
 

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