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In the title compound, C11H13N3O4S, the thia­diazole ring is nearly planar, while the 1,3-dioxane-4,6-dione ring exhibits a half-chair conformation. The NH group makes one intra­molecular contact with a carbonyl group, forming a six-membered ring. The same functional group is involved in an inter­molecular N—H...N hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600969X/bh6071sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680600969X/bh6071Isup2.hkl
Contains datablock I

CCDC reference: 604969

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.116
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.12 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.54 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 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 4 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

5-(5-Ethyl-1,3,4-thiadiazol-2-ylaminomethylene)-2,2-dimethyl-1,3-dioxane- 4,6-dione top
Crystal data top
C11H13N3O4SF(000) = 1184
Mr = 283.30Dx = 1.445 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 10.733 (2) Åθ = 5.4–13.7°
b = 9.842 (1) ŵ = 0.26 mm1
c = 24.650 (2) ÅT = 299 K
V = 2603.9 (6) Å3Prism, colourless
Z = 80.40 × 0.40 × 0.13 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1700 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0
Graphite monochromatorθmax = 26.0°, θmin = 1.7°
ω–2θ scansh = 130
Absorption correction: ψ scan
(North et al., 1968)
k = 120
Tmin = 0.878, Tmax = 0.974l = 030
2543 measured reflections3 standard reflections every 200 reflections
2543 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0539P)2 + 0.4796P]
where P = (Fo2 + 2Fc2)/3
2543 reflections(Δ/σ)max = 0.001
173 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.28 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.19552 (5)0.19525 (7)0.76316 (3)0.03700 (19)
C20.3531 (2)0.2134 (2)0.77513 (9)0.0307 (5)
N30.42119 (18)0.1261 (2)0.74917 (9)0.0370 (5)
N40.35282 (19)0.0383 (2)0.71704 (8)0.0360 (5)
C50.2352 (2)0.0632 (2)0.72069 (9)0.0295 (5)
N60.14439 (18)0.00899 (19)0.69213 (8)0.0310 (5)
H60.06070.01300.69740.049 (8)*
C70.1723 (2)0.1061 (2)0.65640 (9)0.0321 (5)
H70.25630.12500.65100.039*
C80.0883 (2)0.1804 (2)0.62704 (9)0.0318 (5)
C90.0441 (2)0.1553 (3)0.63156 (10)0.0352 (6)
O90.09175 (16)0.07532 (18)0.66262 (8)0.0476 (5)
O100.11977 (16)0.23117 (19)0.59996 (8)0.0477 (5)
C110.0679 (3)0.2951 (3)0.55282 (12)0.0538 (8)
O120.04539 (18)0.3630 (2)0.56625 (8)0.0589 (6)
C130.1339 (3)0.2941 (3)0.59477 (10)0.0424 (6)
O130.23966 (19)0.3339 (2)0.59295 (8)0.0575 (6)
C210.4030 (2)0.3219 (3)0.81180 (11)0.0422 (6)
H21A0.47140.36750.79360.051*
H21B0.33810.38870.81800.051*
C220.4484 (3)0.2700 (3)0.86599 (12)0.0598 (9)
H22A0.47840.34480.88730.090*
H22B0.38090.22640.88470.090*
H22C0.51460.20600.86040.090*
C1110.1598 (3)0.4029 (4)0.53625 (17)0.0921 (14)
H11A0.23770.36100.52690.138*
H11B0.12800.45150.50540.138*
H11C0.17230.46480.56580.138*
C1120.0440 (4)0.1880 (4)0.51050 (13)0.0881 (13)
H11D0.12070.14300.50170.132*
H11E0.01450.12280.52430.132*
H11F0.01050.22980.47850.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0237 (3)0.0389 (3)0.0484 (4)0.0006 (3)0.0004 (3)0.0102 (3)
C20.0248 (11)0.0311 (13)0.0362 (13)0.0032 (10)0.0015 (10)0.0072 (11)
N30.0233 (10)0.0422 (11)0.0454 (12)0.0000 (9)0.0056 (9)0.0024 (10)
N40.0252 (11)0.0406 (12)0.0423 (12)0.0028 (9)0.0026 (9)0.0010 (10)
C50.0252 (12)0.0321 (13)0.0314 (12)0.0005 (10)0.0013 (10)0.0038 (10)
N60.0241 (10)0.0354 (11)0.0334 (11)0.0010 (9)0.0008 (9)0.0007 (9)
C70.0297 (13)0.0371 (13)0.0295 (12)0.0032 (11)0.0021 (10)0.0029 (11)
C80.0322 (13)0.0338 (13)0.0293 (12)0.0003 (11)0.0007 (11)0.0014 (11)
C90.0349 (14)0.0364 (14)0.0342 (14)0.0047 (11)0.0019 (12)0.0014 (12)
O90.0346 (10)0.0512 (12)0.0571 (12)0.0022 (9)0.0062 (9)0.0202 (10)
O100.0337 (10)0.0581 (12)0.0513 (11)0.0047 (9)0.0008 (9)0.0216 (10)
C110.0452 (17)0.068 (2)0.0478 (17)0.0079 (16)0.0086 (13)0.0212 (16)
O120.0518 (13)0.0607 (14)0.0643 (14)0.0127 (11)0.0141 (11)0.0306 (11)
C130.0413 (15)0.0514 (16)0.0344 (14)0.0033 (14)0.0032 (12)0.0070 (13)
O130.0444 (11)0.0693 (14)0.0586 (12)0.0195 (11)0.0010 (10)0.0185 (11)
C210.0335 (13)0.0422 (15)0.0510 (16)0.0082 (12)0.0065 (13)0.0034 (13)
C220.064 (2)0.066 (2)0.0488 (18)0.0009 (17)0.0139 (16)0.0113 (16)
C1110.067 (2)0.097 (3)0.113 (3)0.004 (2)0.029 (2)0.064 (3)
C1120.083 (3)0.137 (4)0.0442 (19)0.016 (3)0.0065 (18)0.008 (2)
Geometric parameters (Å, º) top
S1—C51.722 (2)C11—C1121.505 (5)
S1—C21.727 (2)C11—C1111.505 (4)
C2—N31.297 (3)O12—C131.362 (3)
C2—C211.498 (3)C13—O131.202 (3)
N3—N41.383 (3)C21—C221.511 (4)
N4—C51.289 (3)C21—H21A0.9700
C5—N61.396 (3)C21—H21B0.9700
N6—C71.334 (3)C22—H22A0.9600
N6—H60.9330C22—H22B0.9600
C7—C81.368 (3)C22—H22C0.9600
C7—H70.9300C111—H11A0.9600
C8—C91.446 (3)C111—H11B0.9600
C8—C131.458 (3)C111—H11C0.9600
C9—O91.211 (3)C112—H11D0.9600
C9—O101.351 (3)C112—H11E0.9600
O10—C111.434 (3)C112—H11F0.9600
C11—O121.426 (3)
C5—S1—C286.55 (11)C13—O12—C11118.7 (2)
N3—C2—C21124.7 (2)O13—C13—O12118.5 (2)
N3—C2—S1113.51 (17)O13—C13—C8126.0 (2)
C21—C2—S1121.81 (19)O12—C13—C8115.5 (2)
C2—N3—N4113.45 (19)C2—C21—C22114.1 (2)
C5—N4—N3111.1 (2)C2—C21—H21A108.7
N4—C5—N6123.5 (2)C22—C21—H21A108.7
N4—C5—S1115.35 (18)C2—C21—H21B108.7
N6—C5—S1121.19 (17)C22—C21—H21B108.7
C7—N6—C5122.7 (2)H21A—C21—H21B107.6
C7—N6—H6118.4C21—C22—H22A109.5
C5—N6—H6118.9C21—C22—H22B109.5
N6—C7—C8125.7 (2)H22A—C22—H22B109.5
N6—C7—H7117.1C21—C22—H22C109.5
C8—C7—H7117.1H22A—C22—H22C109.5
C7—C8—C9121.0 (2)H22B—C22—H22C109.5
C7—C8—C13118.6 (2)C11—C111—H11A109.5
C9—C8—C13120.2 (2)C11—C111—H11B109.5
O9—C9—O10118.0 (2)H11A—C111—H11B109.5
O9—C9—C8125.1 (2)C11—C111—H11C109.5
O10—C9—C8116.9 (2)H11A—C111—H11C109.5
C9—O10—C11118.4 (2)H11B—C111—H11C109.5
O12—C11—O10110.4 (2)C11—C112—H11D109.5
O12—C11—C112110.1 (3)C11—C112—H11E109.5
O10—C11—C112108.7 (3)H11D—C112—H11E109.5
O12—C11—C111106.9 (3)C11—C112—H11F109.5
O10—C11—C111105.9 (3)H11D—C112—H11F109.5
C112—C11—C111114.7 (3)H11E—C112—H11F109.5
C5—S1—C2—N30.51 (19)C13—C8—C9—O107.4 (3)
C5—S1—C2—C21178.9 (2)O9—C9—O10—C11161.8 (2)
C21—C2—N3—N4178.7 (2)C8—C9—O10—C1120.6 (3)
S1—C2—N3—N40.7 (3)C9—O10—C11—O1247.8 (3)
C2—N3—N4—C50.5 (3)C9—O10—C11—C11273.1 (3)
N3—N4—C5—N6179.30 (19)C9—O10—C11—C111163.2 (3)
N3—N4—C5—S10.1 (3)O10—C11—O12—C1349.6 (3)
C2—S1—C5—N40.2 (2)C112—C11—O12—C1370.5 (3)
C2—S1—C5—N6179.00 (19)C111—C11—O12—C13164.3 (3)
N4—C5—N6—C73.4 (4)C11—O12—C13—O13159.1 (3)
S1—C5—N6—C7175.74 (18)C11—O12—C13—C823.5 (4)
C5—N6—C7—C8179.9 (2)C7—C8—C13—O133.3 (4)
N6—C7—C8—C91.9 (4)C9—C8—C13—O13171.1 (3)
N6—C7—C8—C13172.5 (2)C7—C8—C13—O12179.5 (2)
C7—C8—C9—O94.3 (4)C9—C8—C13—O126.0 (4)
C13—C8—C9—O9169.9 (2)N3—C2—C21—C2274.5 (3)
C7—C8—C9—O10178.3 (2)S1—C2—C21—C22106.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6···O90.932.042.716 (3)128
N6—H6···N3i0.932.283.098 (3)146
Symmetry code: (i) x1/2, y, z+3/2.
 

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