


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812002978/is5058sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536812002978/is5058Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536812002978/is5058Isup3.cml |
CCDC reference: 868242
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.081
- Data-to-parameter ratio = 18.3
checkCIF/PLATON results
No syntax errors found
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.744 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 -- C10 .. 7.0 su PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 4
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ?
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 1 ALERT level G = General information/check it is not something unexpected 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
5-Amino-2-ethoxy-1,3,4-thiadiazole (1 g, 7.4 mmol) was dissolved in anhydrous dioxane (20 ml) at 80 °C. Triethylamine and benzoyl chloride (8.9 mmol) was added respectively to the above solution. The reaction solution was stirred at 80 °C for 40 minutes. TLC was used to determine the completion of the reaction. The reaction mixture was then cooled to room temperature and the ethylamine hydrochloride filtered off. The white solid was remained after the solvent was distilled off. The solid was recrystallized from ethanol to get analytical sample (product yield 55%). Colourless crystals of (I) were obtained from its ethanol solution by slow evaporation of the solvent at room temperature (m.p. 180 °C). IR (KBr, cm-1) 3120 (NH), 3000 (CH), 2950 (CH), 1680 (C=O), 1580 (C=N). -1H NMR (DMSO-d6, p.p.m.): 12.5 (1H, b, NH), 8.3–7.4 (5H, m, Ph), 4.4 (2H, q, CH2), 1.4 (3H, t, CH3). 13C NMR (DMSO-d6, p.p.m.): 170.5 (amide C=O), 165.2 (O—C=N), 153.2 (C=N), 132.9, 131.6, 128.7, 128.4 (Ph), 68.2 (CH2), 14.4 (CH3). Anal. Calcd. For C11H11N3O2S: C 53.00, H 4.456, N 16.86, S 12.86. Found: C 53.07, H 4.46, N 16.83, S 13.29.
Atom H6 of the NH group was located in a difference Fourier map and refined freely [refined distance = 0.86 (2) Å]. Other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(carrier C) for aromatic and methylene or 1.5Ueq(carrier C) for methyl H atoms.
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C11H11N3O2S | F(000) = 520 |
Mr = 249.29 | Dx = 1.433 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1448 reflections |
a = 3.9797 (5) Å | θ = 2.8–18.7° |
b = 20.138 (3) Å | µ = 0.27 mm−1 |
c = 14.4305 (18) Å | T = 296 K |
β = 92.036 (2)° | Needle, colourless |
V = 1155.8 (2) Å3 | 0.27 × 0.12 × 0.11 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 1287 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.114 |
ϕ and ω scans | θmax = 28.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −5→5 |
Tmin = 0.956, Tmax = 0.965 | k = −26→26 |
22225 measured reflections | l = −19→19 |
2891 independent 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.74 | w = 1/[σ2(Fo2) + (0.0257P)2] where P = (Fo2 + 2Fc2)/3 |
2891 reflections | (Δ/σ)max < 0.001 |
158 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C11H11N3O2S | V = 1155.8 (2) Å3 |
Mr = 249.29 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 3.9797 (5) Å | µ = 0.27 mm−1 |
b = 20.138 (3) Å | T = 296 K |
c = 14.4305 (18) Å | 0.27 × 0.12 × 0.11 mm |
β = 92.036 (2)° |
Bruker SMART CCD area-detector diffractometer | 2891 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 1287 reflections with I > 2σ(I) |
Tmin = 0.956, Tmax = 0.965 | Rint = 0.114 |
22225 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.74 | Δρmax = 0.19 e Å−3 |
2891 reflections | Δρmin = −0.19 e Å−3 |
158 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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 | ||
S1 | 0.39663 (15) | 0.34946 (3) | 0.62317 (4) | 0.04682 (18) | |
C2 | 0.2359 (5) | 0.42298 (9) | 0.57867 (14) | 0.0375 (5) | |
N3 | 0.2325 (5) | 0.42812 (8) | 0.48901 (12) | 0.0467 (5) | |
N4 | 0.3654 (5) | 0.37174 (8) | 0.44715 (11) | 0.0473 (5) | |
C5 | 0.4558 (5) | 0.32859 (10) | 0.50836 (14) | 0.0411 (5) | |
N6 | 0.1165 (5) | 0.47337 (9) | 0.63320 (12) | 0.0433 (5) | |
H6 | 0.021 (6) | 0.5057 (12) | 0.6040 (16) | 0.082 (9)* | |
C7 | 0.1183 (5) | 0.46904 (10) | 0.72786 (14) | 0.0398 (5) | |
O8 | 0.2192 (4) | 0.41880 (7) | 0.76704 (9) | 0.0545 (4) | |
C9 | −0.0024 (5) | 0.52767 (10) | 0.77924 (14) | 0.0399 (5) | |
C10 | −0.1415 (6) | 0.51700 (12) | 0.86450 (15) | 0.0549 (7) | |
H10 | −0.1629 | 0.4739 | 0.8868 | 0.066* | |
C11 | −0.2486 (6) | 0.56979 (13) | 0.91657 (16) | 0.0608 (7) | |
H11 | −0.3439 | 0.5623 | 0.9736 | 0.073* | |
C12 | −0.2143 (6) | 0.63343 (13) | 0.88413 (16) | 0.0621 (7) | |
H12 | −0.288 | 0.6691 | 0.919 | 0.075* | |
C13 | −0.0712 (6) | 0.64450 (11) | 0.80031 (16) | 0.0606 (7) | |
H13 | −0.0444 | 0.6877 | 0.7791 | 0.073* | |
C14 | 0.0330 (6) | 0.59171 (10) | 0.74726 (15) | 0.0491 (6) | |
H14 | 0.1268 | 0.5994 | 0.6901 | 0.059* | |
O15 | 0.5894 (4) | 0.26919 (7) | 0.49063 (10) | 0.0541 (4) | |
C16 | 0.6596 (6) | 0.25697 (10) | 0.39481 (14) | 0.0516 (6) | |
H16A | 0.8359 | 0.2865 | 0.3751 | 0.062* | |
H16B | 0.4597 | 0.2649 | 0.3559 | 0.062* | |
C17 | 0.7689 (6) | 0.18619 (11) | 0.38643 (15) | 0.0639 (7) | |
H17A | 0.8181 | 0.1769 | 0.3231 | 0.096* | |
H17B | 0.5922 | 0.1574 | 0.4057 | 0.096* | |
H17C | 0.9666 | 0.1789 | 0.4251 | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0621 (4) | 0.0364 (3) | 0.0421 (3) | 0.0089 (3) | 0.0035 (3) | 0.0037 (3) |
C2 | 0.0460 (14) | 0.0303 (12) | 0.0362 (12) | 0.0008 (10) | 0.0005 (10) | −0.0005 (10) |
N3 | 0.0673 (14) | 0.0351 (11) | 0.0377 (11) | 0.0110 (9) | 0.0004 (9) | −0.0021 (9) |
N4 | 0.0638 (14) | 0.0364 (11) | 0.0417 (11) | 0.0106 (9) | 0.0004 (9) | −0.0033 (9) |
C5 | 0.0478 (15) | 0.0334 (12) | 0.0420 (13) | 0.0021 (11) | 0.0024 (11) | −0.0026 (11) |
N6 | 0.0624 (14) | 0.0343 (11) | 0.0330 (11) | 0.0088 (10) | −0.0004 (9) | 0.0006 (9) |
C7 | 0.0406 (14) | 0.0376 (13) | 0.0411 (13) | −0.0021 (10) | 0.0011 (10) | 0.0030 (11) |
O8 | 0.0763 (12) | 0.0425 (9) | 0.0445 (9) | 0.0106 (8) | 0.0006 (8) | 0.0078 (7) |
C9 | 0.0428 (14) | 0.0421 (13) | 0.0348 (12) | 0.0002 (11) | −0.0010 (10) | −0.0013 (11) |
C10 | 0.0631 (18) | 0.0525 (16) | 0.0492 (15) | −0.0006 (13) | 0.0017 (12) | −0.0016 (12) |
C11 | 0.0647 (18) | 0.0749 (19) | 0.0436 (15) | −0.0008 (15) | 0.0128 (12) | −0.0064 (14) |
C12 | 0.0724 (19) | 0.0667 (19) | 0.0470 (16) | 0.0162 (15) | −0.0007 (13) | −0.0157 (14) |
C13 | 0.090 (2) | 0.0438 (15) | 0.0480 (15) | 0.0117 (14) | −0.0032 (14) | −0.0036 (13) |
C14 | 0.0667 (17) | 0.0426 (14) | 0.0381 (13) | 0.0023 (12) | 0.0013 (11) | −0.0005 (11) |
O15 | 0.0777 (12) | 0.0369 (9) | 0.0483 (10) | 0.0159 (8) | 0.0091 (8) | −0.0015 (7) |
C16 | 0.0564 (17) | 0.0477 (15) | 0.0510 (15) | 0.0077 (12) | 0.0056 (12) | −0.0087 (12) |
C17 | 0.0682 (18) | 0.0512 (16) | 0.0720 (18) | 0.0097 (13) | −0.0032 (14) | −0.0174 (13) |
S1—C2 | 1.727 (2) | C11—C12 | 1.373 (3) |
S1—C5 | 1.733 (2) | C11—H11 | 0.93 |
C2—N3 | 1.298 (2) | C12—C13 | 1.373 (3) |
C2—N6 | 1.379 (2) | C12—H12 | 0.93 |
N3—N4 | 1.399 (2) | C13—C14 | 1.382 (3) |
N4—C5 | 1.282 (2) | C13—H13 | 0.93 |
C5—O15 | 1.337 (2) | C14—H14 | 0.93 |
N6—C7 | 1.368 (2) | O15—C16 | 1.442 (2) |
N6—H6 | 0.86 (2) | C16—C17 | 1.496 (3) |
C7—O8 | 1.220 (2) | C16—H16A | 0.97 |
C7—C9 | 1.483 (3) | C16—H16B | 0.97 |
C9—C14 | 1.379 (3) | C17—H17A | 0.96 |
C9—C10 | 1.384 (3) | C17—H17B | 0.96 |
C10—C11 | 1.378 (3) | C17—H17C | 0.96 |
C10—H10 | 0.93 | ||
C2—S1—C5 | 85.05 (10) | C10—C11—H11 | 120.1 |
N3—C2—N6 | 121.25 (18) | C11—C12—C13 | 120.1 (2) |
N3—C2—S1 | 115.45 (15) | C11—C12—H12 | 120 |
N6—C2—S1 | 123.31 (16) | C13—C12—H12 | 120 |
C2—N3—N4 | 112.03 (16) | C12—C13—C14 | 120.3 (2) |
C5—N4—N3 | 110.73 (17) | C12—C13—H13 | 119.8 |
N4—C5—O15 | 125.34 (19) | C14—C13—H13 | 119.8 |
N4—C5—S1 | 116.75 (16) | C9—C14—C13 | 119.9 (2) |
O15—C5—S1 | 117.92 (15) | C9—C14—H14 | 120.1 |
C7—N6—C2 | 122.22 (19) | C13—C14—H14 | 120.1 |
C7—N6—H6 | 121.7 (16) | C5—O15—C16 | 115.34 (15) |
C2—N6—H6 | 115.7 (16) | O15—C16—C17 | 107.87 (17) |
O8—C7—N6 | 120.35 (19) | O15—C16—H16A | 110.1 |
O8—C7—C9 | 122.38 (19) | C17—C16—H16A | 110.1 |
N6—C7—C9 | 117.26 (19) | O15—C16—H16B | 110.1 |
C14—C9—C10 | 119.5 (2) | C17—C16—H16B | 110.1 |
C14—C9—C7 | 122.6 (2) | H16A—C16—H16B | 108.4 |
C10—C9—C7 | 117.9 (2) | C16—C17—H17A | 109.5 |
C11—C10—C9 | 120.4 (2) | C16—C17—H17B | 109.5 |
C11—C10—H10 | 119.8 | H17A—C17—H17B | 109.5 |
C9—C10—H10 | 119.8 | C16—C17—H17C | 109.5 |
C12—C11—C10 | 119.8 (2) | H17A—C17—H17C | 109.5 |
C12—C11—H11 | 120.1 | H17B—C17—H17C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6···N3i | 0.86 (2) | 2.12 (2) | 2.967 (3) | 169 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C11H11N3O2S |
Mr | 249.29 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 3.9797 (5), 20.138 (3), 14.4305 (18) |
β (°) | 92.036 (2) |
V (Å3) | 1155.8 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.27 × 0.12 × 0.11 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.956, 0.965 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22225, 2891, 1287 |
Rint | 0.114 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.081, 0.74 |
No. of reflections | 2891 |
No. of parameters | 158 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.19 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6···N3i | 0.86 (2) | 2.12 (2) | 2.967 (3) | 169 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
5-Amino-2H-1,2,4-thiadiazol-3-one is a five-membered ring analog of cytosine. 5-Amino-3H-1,3,4-thiadiazol-2-one is an isomer of 5-amino-2H-1,2,4-thiadiazol-3-one. The analogs of cytosine have potential to have biological activities (Parkanyi et al., 1989). Thus, we attempted synthesis of derivatives of 5-amino-3H-1,3,4-thiadiazol-2-one (Cho et al., 1996). The title compound, 2-benzoylamino-5-ethoxy-1,3,4-thiadiazole (I) is an intermediate to prepare 5-benzolamino-3H-1,3,4-thiadiazolin-2-one via hydrolysis.
The five-membered 1,3,4-thiadiazol-2-yl unit is planar, with an r.m.s. deviation of 0.003 Å from the corresponding squares plane defined by the seven constituent atoms. The bond distances of C2—N3 and C5—N4 [1.298 (2) and 1.282 (2) Å] in five-membered heterocyclic ring are shorter than those of C2—N6 and C7—N6 [1.379 (2) and 1.369 (2) Å], which is consistent with double bond character. A pair of intermolecular N6—H6···N3i [symmetry code: (i) -x, -y + 1, -z + 1] hydrogen bonds link two molecules into an inversion dimer (Fig. 2 and Table 1), which stabilizes the crystal structure.