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organic compounds
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—HN hydrogen bond.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600969X/bh6071sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680600969X/bh6071Isup2.hkl |
CCDC reference: 604969
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (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
C11H13N3O4S | F(000) = 1184 |
Mr = 283.30 | Dx = 1.445 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 10.733 (2) Å | θ = 5.4–13.7° |
b = 9.842 (1) Å | µ = 0.26 mm−1 |
c = 24.650 (2) Å | T = 299 K |
V = 2603.9 (6) Å3 | Prism, colourless |
Z = 8 | 0.40 × 0.40 × 0.13 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 1700 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
ω–2θ scans | h = −13→0 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→0 |
Tmin = 0.878, Tmax = 0.974 | l = 0→30 |
2543 measured reflections | 3 standard reflections every 200 reflections |
2543 independent reflections | intensity decay: 1% |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-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 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.19552 (5) | −0.19525 (7) | 0.76316 (3) | 0.03700 (19) | |
C2 | 0.3531 (2) | −0.2134 (2) | 0.77513 (9) | 0.0307 (5) | |
N3 | 0.42119 (18) | −0.1261 (2) | 0.74917 (9) | 0.0370 (5) | |
N4 | 0.35282 (19) | −0.0383 (2) | 0.71704 (8) | 0.0360 (5) | |
C5 | 0.2352 (2) | −0.0632 (2) | 0.72069 (9) | 0.0295 (5) | |
N6 | 0.14439 (18) | 0.00899 (19) | 0.69213 (8) | 0.0310 (5) | |
H6 | 0.0607 | −0.0130 | 0.6974 | 0.049 (8)* | |
C7 | 0.1723 (2) | 0.1061 (2) | 0.65640 (9) | 0.0321 (5) | |
H7 | 0.2563 | 0.1250 | 0.6510 | 0.039* | |
C8 | 0.0883 (2) | 0.1804 (2) | 0.62704 (9) | 0.0318 (5) | |
C9 | −0.0441 (2) | 0.1553 (3) | 0.63156 (10) | 0.0352 (6) | |
O9 | −0.09175 (16) | 0.07532 (18) | 0.66262 (8) | 0.0476 (5) | |
O10 | −0.11977 (16) | 0.23117 (19) | 0.59996 (8) | 0.0477 (5) | |
C11 | −0.0679 (3) | 0.2951 (3) | 0.55282 (12) | 0.0538 (8) | |
O12 | 0.04539 (18) | 0.3630 (2) | 0.56625 (8) | 0.0589 (6) | |
C13 | 0.1339 (3) | 0.2941 (3) | 0.59477 (10) | 0.0424 (6) | |
O13 | 0.23966 (19) | 0.3339 (2) | 0.59295 (8) | 0.0575 (6) | |
C21 | 0.4030 (2) | −0.3219 (3) | 0.81180 (11) | 0.0422 (6) | |
H21A | 0.4714 | −0.3675 | 0.7936 | 0.051* | |
H21B | 0.3381 | −0.3887 | 0.8180 | 0.051* | |
C22 | 0.4484 (3) | −0.2700 (3) | 0.86599 (12) | 0.0598 (9) | |
H22A | 0.4784 | −0.3448 | 0.8873 | 0.090* | |
H22B | 0.3809 | −0.2264 | 0.8847 | 0.090* | |
H22C | 0.5146 | −0.2060 | 0.8604 | 0.090* | |
C111 | −0.1598 (3) | 0.4029 (4) | 0.53625 (17) | 0.0921 (14) | |
H11A | −0.2377 | 0.3610 | 0.5269 | 0.138* | |
H11B | −0.1280 | 0.4515 | 0.5054 | 0.138* | |
H11C | −0.1723 | 0.4648 | 0.5658 | 0.138* | |
C112 | −0.0440 (4) | 0.1880 (4) | 0.51050 (13) | 0.0881 (13) | |
H11D | −0.1207 | 0.1430 | 0.5017 | 0.132* | |
H11E | 0.0145 | 0.1228 | 0.5243 | 0.132* | |
H11F | −0.0105 | 0.2298 | 0.4785 | 0.132* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0237 (3) | 0.0389 (3) | 0.0484 (4) | 0.0006 (3) | −0.0004 (3) | 0.0102 (3) |
C2 | 0.0248 (11) | 0.0311 (13) | 0.0362 (13) | 0.0032 (10) | −0.0015 (10) | −0.0072 (11) |
N3 | 0.0233 (10) | 0.0422 (11) | 0.0454 (12) | 0.0000 (9) | −0.0056 (9) | −0.0024 (10) |
N4 | 0.0252 (11) | 0.0406 (12) | 0.0423 (12) | −0.0028 (9) | −0.0026 (9) | 0.0010 (10) |
C5 | 0.0252 (12) | 0.0321 (13) | 0.0314 (12) | 0.0005 (10) | −0.0013 (10) | −0.0038 (10) |
N6 | 0.0241 (10) | 0.0354 (11) | 0.0334 (11) | 0.0010 (9) | −0.0008 (9) | 0.0007 (9) |
C7 | 0.0297 (13) | 0.0371 (13) | 0.0295 (12) | −0.0032 (11) | 0.0021 (10) | −0.0029 (11) |
C8 | 0.0322 (13) | 0.0338 (13) | 0.0293 (12) | 0.0003 (11) | 0.0007 (11) | 0.0014 (11) |
C9 | 0.0349 (14) | 0.0364 (14) | 0.0342 (14) | 0.0047 (11) | 0.0019 (12) | 0.0014 (12) |
O9 | 0.0346 (10) | 0.0512 (12) | 0.0571 (12) | 0.0022 (9) | 0.0062 (9) | 0.0202 (10) |
O10 | 0.0337 (10) | 0.0581 (12) | 0.0513 (11) | 0.0047 (9) | −0.0008 (9) | 0.0216 (10) |
C11 | 0.0452 (17) | 0.068 (2) | 0.0478 (17) | −0.0079 (16) | −0.0086 (13) | 0.0212 (16) |
O12 | 0.0518 (13) | 0.0607 (14) | 0.0643 (14) | −0.0127 (11) | −0.0141 (11) | 0.0306 (11) |
C13 | 0.0413 (15) | 0.0514 (16) | 0.0344 (14) | −0.0033 (14) | −0.0032 (12) | 0.0070 (13) |
O13 | 0.0444 (11) | 0.0693 (14) | 0.0586 (12) | −0.0195 (11) | −0.0010 (10) | 0.0185 (11) |
C21 | 0.0335 (13) | 0.0422 (15) | 0.0510 (16) | 0.0082 (12) | −0.0065 (13) | 0.0034 (13) |
C22 | 0.064 (2) | 0.066 (2) | 0.0488 (18) | −0.0009 (17) | −0.0139 (16) | 0.0113 (16) |
C111 | 0.067 (2) | 0.097 (3) | 0.113 (3) | −0.004 (2) | −0.029 (2) | 0.064 (3) |
C112 | 0.083 (3) | 0.137 (4) | 0.0442 (19) | −0.016 (3) | −0.0065 (18) | −0.008 (2) |
Geometric parameters (Å, º) top
S1—C5 | 1.722 (2) | C11—C112 | 1.505 (5) |
S1—C2 | 1.727 (2) | C11—C111 | 1.505 (4) |
C2—N3 | 1.297 (3) | O12—C13 | 1.362 (3) |
C2—C21 | 1.498 (3) | C13—O13 | 1.202 (3) |
N3—N4 | 1.383 (3) | C21—C22 | 1.511 (4) |
N4—C5 | 1.289 (3) | C21—H21A | 0.9700 |
C5—N6 | 1.396 (3) | C21—H21B | 0.9700 |
N6—C7 | 1.334 (3) | C22—H22A | 0.9600 |
N6—H6 | 0.9330 | C22—H22B | 0.9600 |
C7—C8 | 1.368 (3) | C22—H22C | 0.9600 |
C7—H7 | 0.9300 | C111—H11A | 0.9600 |
C8—C9 | 1.446 (3) | C111—H11B | 0.9600 |
C8—C13 | 1.458 (3) | C111—H11C | 0.9600 |
C9—O9 | 1.211 (3) | C112—H11D | 0.9600 |
C9—O10 | 1.351 (3) | C112—H11E | 0.9600 |
O10—C11 | 1.434 (3) | C112—H11F | 0.9600 |
C11—O12 | 1.426 (3) | ||
C5—S1—C2 | 86.55 (11) | C13—O12—C11 | 118.7 (2) |
N3—C2—C21 | 124.7 (2) | O13—C13—O12 | 118.5 (2) |
N3—C2—S1 | 113.51 (17) | O13—C13—C8 | 126.0 (2) |
C21—C2—S1 | 121.81 (19) | O12—C13—C8 | 115.5 (2) |
C2—N3—N4 | 113.45 (19) | C2—C21—C22 | 114.1 (2) |
C5—N4—N3 | 111.1 (2) | C2—C21—H21A | 108.7 |
N4—C5—N6 | 123.5 (2) | C22—C21—H21A | 108.7 |
N4—C5—S1 | 115.35 (18) | C2—C21—H21B | 108.7 |
N6—C5—S1 | 121.19 (17) | C22—C21—H21B | 108.7 |
C7—N6—C5 | 122.7 (2) | H21A—C21—H21B | 107.6 |
C7—N6—H6 | 118.4 | C21—C22—H22A | 109.5 |
C5—N6—H6 | 118.9 | C21—C22—H22B | 109.5 |
N6—C7—C8 | 125.7 (2) | H22A—C22—H22B | 109.5 |
N6—C7—H7 | 117.1 | C21—C22—H22C | 109.5 |
C8—C7—H7 | 117.1 | H22A—C22—H22C | 109.5 |
C7—C8—C9 | 121.0 (2) | H22B—C22—H22C | 109.5 |
C7—C8—C13 | 118.6 (2) | C11—C111—H11A | 109.5 |
C9—C8—C13 | 120.2 (2) | C11—C111—H11B | 109.5 |
O9—C9—O10 | 118.0 (2) | H11A—C111—H11B | 109.5 |
O9—C9—C8 | 125.1 (2) | C11—C111—H11C | 109.5 |
O10—C9—C8 | 116.9 (2) | H11A—C111—H11C | 109.5 |
C9—O10—C11 | 118.4 (2) | H11B—C111—H11C | 109.5 |
O12—C11—O10 | 110.4 (2) | C11—C112—H11D | 109.5 |
O12—C11—C112 | 110.1 (3) | C11—C112—H11E | 109.5 |
O10—C11—C112 | 108.7 (3) | H11D—C112—H11E | 109.5 |
O12—C11—C111 | 106.9 (3) | C11—C112—H11F | 109.5 |
O10—C11—C111 | 105.9 (3) | H11D—C112—H11F | 109.5 |
C112—C11—C111 | 114.7 (3) | H11E—C112—H11F | 109.5 |
C5—S1—C2—N3 | 0.51 (19) | C13—C8—C9—O10 | 7.4 (3) |
C5—S1—C2—C21 | −178.9 (2) | O9—C9—O10—C11 | −161.8 (2) |
C21—C2—N3—N4 | 178.7 (2) | C8—C9—O10—C11 | 20.6 (3) |
S1—C2—N3—N4 | −0.7 (3) | C9—O10—C11—O12 | −47.8 (3) |
C2—N3—N4—C5 | 0.5 (3) | C9—O10—C11—C112 | 73.1 (3) |
N3—N4—C5—N6 | −179.30 (19) | C9—O10—C11—C111 | −163.2 (3) |
N3—N4—C5—S1 | −0.1 (3) | O10—C11—O12—C13 | 49.6 (3) |
C2—S1—C5—N4 | −0.2 (2) | C112—C11—O12—C13 | −70.5 (3) |
C2—S1—C5—N6 | 179.00 (19) | C111—C11—O12—C13 | 164.3 (3) |
N4—C5—N6—C7 | 3.4 (4) | C11—O12—C13—O13 | 159.1 (3) |
S1—C5—N6—C7 | −175.74 (18) | C11—O12—C13—C8 | −23.5 (4) |
C5—N6—C7—C8 | 179.9 (2) | C7—C8—C13—O13 | −3.3 (4) |
N6—C7—C8—C9 | −1.9 (4) | C9—C8—C13—O13 | 171.1 (3) |
N6—C7—C8—C13 | 172.5 (2) | C7—C8—C13—O12 | 179.5 (2) |
C7—C8—C9—O9 | 4.3 (4) | C9—C8—C13—O12 | −6.0 (4) |
C13—C8—C9—O9 | −169.9 (2) | N3—C2—C21—C22 | 74.5 (3) |
C7—C8—C9—O10 | −178.3 (2) | S1—C2—C21—C22 | −106.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6···O9 | 0.93 | 2.04 | 2.716 (3) | 128 |
N6—H6···N3i | 0.93 | 2.28 | 3.098 (3) | 146 |
Symmetry code: (i) x−1/2, y, −z+3/2. |
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