Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047228/at2411sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047228/at2411Isup2.hkl |
CCDC reference: 667282
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.053
- wR factor = 0.157
- Data-to-parameter ratio = 18.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.21 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.65 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT415_ALERT_2_C Short Inter D-H..H-X H1 .. H12A .. 2.12 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.60 Deg. C16' -C15 -C16 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 17.50 Deg. H15A -C15 -H15C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.20 Deg. H15B -C15 -H15D 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 16
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of 5,5-dimethyl-3-phenylamino-2-thioxo-4-imidazolidione (0.71 g, 3 mmol), hexyl bromide (0.50 g, 3 mmol) and solid potassium carbonate (0.83 g, 6 mmol) in CH3CN (15 ml) was stirred for 5 h at 323 K and was filtered. The filtrate was condensed, and the residue was recrystallized from diethyl ether and petroleum ether (1:3) to give the title compound (I) in yield of 83% (m.p. 355 K). Suitable crystals were obtained by slow evaporation of a solution of (I) in dichloromethane and petroleum ether at room temperature.
All H atoms were located in difference maps and treated as riding atoms, except those at N1, with the following distance restraints: C—H = 0.93 Å, Uiso = 1.2Ueq(C) for Csp2, C—H = 0.97 Å, Uiso = 1.2Ueq(C) for CH2, N—H = 0.86 Å, Uiso = 1.2Ueq(N) for NH2, C—H = 0.96 Å, Uiso = 1.5Ueq(C) for CH3.
Imidazolinones are important heterocycles exhibiting remarkable biological activities, especially fungicidal activities (Khodair et al., 1998). Since a novel mitochondrial respiratory inhibitor (Fenamidone) was found to show high fungicidal activities, many other 2-alkylthio imidazolinones have been synthesized to evaluate their fungicidal activities (Bruhn et al., 1998). We obtained the title compound, (I), which may be used as a new precursor for obtaining bioactive molecules. The crystal structure of (I) is presented here.
Atom S1, N1 and the five-membered imidazolone ring are essentially planar. The C16 and C17 atoms, and the hydrogen atoms attached to C15, C16 and C17 are disordered over two sites, with refined occupancies of 0.309 (7) and 0.691 (7) (Fig. 1). The bond lengths involving atom C9 indicate a degree of electron delocalization (Yuan et al., 2006). As can be seen from the packing diagram (Fig. 2), intermolecular N—H···N and C—H···O hydrogen bondings (Table 1) link the molecules.
Imidazolinones have been prepared and their biological activities, especially their fungicidal activities, have been studied by Khodair et al. (1998) and Bruhn et al. (1998). For related literature, see: Yuan et al., 2006.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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: SHELXTL (Sheldrick, 2001).
C17H25N3OS | F(000) = 688 |
Mr = 319.46 | Dx = 1.192 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3820 reflections |
a = 6.2528 (5) Å | θ = 2.5–27.4° |
b = 14.8770 (11) Å | µ = 0.19 mm−1 |
c = 19.1740 (15) Å | T = 292 K |
β = 93.806 (1)° | Block, colourless |
V = 1779.7 (2) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 4037 independent reflections |
Radiation source: fine-focus sealed tube | 3099 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→5 |
Tmin = 0.964, Tmax = 0.982 | k = −19→17 |
10984 measured reflections | l = −21→24 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0936P)2 + 0.0291P] where P = (Fo2 + 2Fc2)/3 |
4037 reflections | (Δ/σ)max < 0.001 |
222 parameters | Δρmax = 0.49 e Å−3 |
16 restraints | Δρmin = −0.44 e Å−3 |
C17H25N3OS | V = 1779.7 (2) Å3 |
Mr = 319.46 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.2528 (5) Å | µ = 0.19 mm−1 |
b = 14.8770 (11) Å | T = 292 K |
c = 19.1740 (15) Å | 0.20 × 0.20 × 0.10 mm |
β = 93.806 (1)° |
Bruker SMART CCD area-detector diffractometer | 4037 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3099 reflections with I > 2σ(I) |
Tmin = 0.964, Tmax = 0.982 | Rint = 0.037 |
10984 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 16 restraints |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.49 e Å−3 |
4037 reflections | Δρmin = −0.44 e Å−3 |
222 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 | Occ. (<1) | |
N1 | 1.0843 (2) | 0.63981 (9) | 0.23056 (7) | 0.0404 (3) | |
H1 | 1.1701 | 0.6276 | 0.1986 | 0.049* | |
N2 | 0.8961 (2) | 0.68754 (9) | 0.21568 (8) | 0.0401 (3) | |
N3 | 0.5428 (2) | 0.70044 (9) | 0.18400 (8) | 0.0444 (4) | |
O1 | 0.9892 (2) | 0.82995 (9) | 0.25323 (9) | 0.0652 (4) | |
S1 | 0.72154 (8) | 0.53663 (3) | 0.16269 (3) | 0.04854 (19) | |
C1 | 0.9848 (3) | 0.62221 (14) | 0.35171 (11) | 0.0550 (5) | |
H1A | 0.8532 | 0.6499 | 0.3412 | 0.066* | |
C2 | 1.0374 (4) | 0.59096 (16) | 0.41849 (12) | 0.0708 (7) | |
H2 | 0.9403 | 0.5982 | 0.4528 | 0.085* | |
C3 | 1.2297 (4) | 0.54941 (17) | 0.43532 (12) | 0.0732 (7) | |
H3 | 1.2634 | 0.5287 | 0.4805 | 0.088* | |
C4 | 1.3712 (4) | 0.53891 (16) | 0.38448 (13) | 0.0697 (7) | |
H4 | 1.5020 | 0.5107 | 0.3953 | 0.084* | |
C5 | 1.3226 (3) | 0.56953 (14) | 0.31739 (11) | 0.0543 (5) | |
H5 | 1.4202 | 0.5615 | 0.2834 | 0.065* | |
C6 | 1.1288 (3) | 0.61219 (11) | 0.30042 (9) | 0.0408 (4) | |
C7 | 0.8579 (3) | 0.77681 (11) | 0.23033 (10) | 0.0449 (4) | |
C8 | 0.6195 (3) | 0.78913 (11) | 0.21235 (11) | 0.0498 (5) | |
C9 | 0.7054 (3) | 0.64835 (11) | 0.18752 (8) | 0.0374 (4) | |
C10 | 0.5790 (4) | 0.86296 (15) | 0.15830 (15) | 0.0820 (8) | |
H10A | 0.6386 | 0.8457 | 0.1154 | 0.123* | |
H10B | 0.6453 | 0.9177 | 0.1752 | 0.123* | |
H10C | 0.4274 | 0.8722 | 0.1501 | 0.123* | |
C11 | 0.5136 (3) | 0.80949 (17) | 0.28010 (15) | 0.0739 (7) | |
H11A | 0.3634 | 0.8203 | 0.2699 | 0.111* | |
H11B | 0.5787 | 0.8618 | 0.3018 | 0.111* | |
H11C | 0.5320 | 0.7591 | 0.3112 | 0.111* | |
C12 | 0.4533 (3) | 0.51978 (13) | 0.12390 (11) | 0.0532 (5) | |
H12A | 0.3519 | 0.5205 | 0.1600 | 0.064* | |
H12B | 0.4164 | 0.5681 | 0.0913 | 0.064* | |
C13 | 0.4406 (3) | 0.43057 (12) | 0.08595 (10) | 0.0483 (5) | |
H13A | 0.5435 | 0.4302 | 0.0503 | 0.058* | |
H13B | 0.4789 | 0.3827 | 0.1188 | 0.058* | |
C14 | 0.2194 (3) | 0.41275 (14) | 0.05226 (11) | 0.0574 (5) | |
H14A | 0.1164 | 0.4183 | 0.0877 | 0.069* | |
H14B | 0.1864 | 0.4589 | 0.0175 | 0.069* | |
C15 | 0.1907 (4) | 0.32247 (14) | 0.01789 (13) | 0.0706 (7) | |
H15A | 0.2309 | 0.2754 | 0.0512 | 0.085* | 0.691 (7) |
H15B | 0.2826 | 0.3179 | −0.0208 | 0.085* | 0.691 (7) |
H15C | 0.1875 | 0.2791 | 0.0556 | 0.085* | 0.309 (7) |
H15D | 0.3216 | 0.3110 | −0.0050 | 0.085* | 0.309 (7) |
C16 | −0.0461 (7) | 0.3103 (3) | −0.0092 (3) | 0.0754 (15) | 0.691 (7) |
H16A | −0.1365 | 0.3178 | 0.0296 | 0.091* | 0.691 (7) |
H16B | −0.0834 | 0.3571 | −0.0431 | 0.091* | 0.691 (7) |
C17 | −0.0929 (7) | 0.2202 (3) | −0.0426 (3) | 0.0909 (17) | 0.691 (7) |
H17A | 0.0061 | 0.2093 | −0.0779 | 0.136* | 0.691 (7) |
H17B | −0.2366 | 0.2198 | −0.0636 | 0.136* | 0.691 (7) |
H17C | −0.0778 | 0.1740 | −0.0077 | 0.136* | 0.691 (7) |
C16' | 0.0146 (17) | 0.2957 (9) | −0.0348 (5) | 0.081 (4) | 0.309 (7) |
H16C | −0.0410 | 0.3465 | −0.0620 | 0.097* | 0.309 (7) |
H16D | 0.0589 | 0.2487 | −0.0658 | 0.097* | 0.309 (7) |
C17' | −0.141 (2) | 0.2625 (10) | 0.0151 (7) | 0.120 (5) | 0.309 (7) |
H17D | −0.0639 | 0.2387 | 0.0561 | 0.179* | 0.309 (7) |
H17E | −0.2283 | 0.2161 | −0.0068 | 0.179* | 0.309 (7) |
H17F | −0.2304 | 0.3112 | 0.0283 | 0.179* | 0.309 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0312 (7) | 0.0454 (8) | 0.0447 (8) | 0.0094 (6) | 0.0031 (6) | −0.0019 (6) |
N2 | 0.0296 (7) | 0.0379 (7) | 0.0524 (9) | 0.0038 (6) | −0.0010 (6) | −0.0040 (6) |
N3 | 0.0350 (8) | 0.0358 (7) | 0.0613 (9) | 0.0019 (6) | −0.0054 (7) | −0.0079 (6) |
O1 | 0.0362 (8) | 0.0492 (8) | 0.1091 (12) | −0.0066 (6) | −0.0028 (7) | −0.0211 (8) |
S1 | 0.0460 (3) | 0.0359 (3) | 0.0621 (3) | 0.00756 (19) | −0.0089 (2) | −0.00951 (19) |
C1 | 0.0502 (12) | 0.0572 (12) | 0.0587 (12) | 0.0017 (9) | 0.0111 (9) | −0.0004 (9) |
C2 | 0.0889 (19) | 0.0719 (15) | 0.0536 (13) | −0.0121 (13) | 0.0192 (12) | 0.0029 (11) |
C3 | 0.0871 (19) | 0.0748 (15) | 0.0557 (13) | −0.0169 (13) | −0.0106 (13) | 0.0155 (11) |
C4 | 0.0591 (14) | 0.0749 (15) | 0.0725 (15) | −0.0030 (11) | −0.0150 (11) | 0.0225 (11) |
C5 | 0.0407 (11) | 0.0651 (12) | 0.0566 (11) | 0.0042 (9) | −0.0002 (9) | 0.0090 (9) |
C6 | 0.0364 (9) | 0.0386 (9) | 0.0470 (10) | −0.0065 (7) | −0.0007 (7) | −0.0020 (7) |
C7 | 0.0344 (9) | 0.0395 (9) | 0.0608 (11) | −0.0001 (7) | 0.0028 (8) | −0.0047 (8) |
C8 | 0.0337 (9) | 0.0358 (9) | 0.0786 (13) | 0.0024 (7) | −0.0053 (9) | −0.0123 (8) |
C9 | 0.0362 (9) | 0.0354 (8) | 0.0401 (9) | 0.0006 (7) | −0.0005 (7) | −0.0026 (7) |
C10 | 0.0710 (16) | 0.0419 (11) | 0.129 (2) | 0.0058 (11) | −0.0260 (15) | 0.0086 (12) |
C11 | 0.0382 (11) | 0.0704 (14) | 0.1143 (19) | −0.0057 (10) | 0.0140 (11) | −0.0458 (13) |
C12 | 0.0461 (11) | 0.0480 (10) | 0.0640 (12) | 0.0049 (8) | −0.0088 (9) | −0.0175 (9) |
C13 | 0.0530 (12) | 0.0397 (9) | 0.0513 (11) | 0.0012 (8) | −0.0042 (8) | −0.0066 (8) |
C14 | 0.0524 (12) | 0.0529 (11) | 0.0658 (13) | −0.0040 (9) | −0.0058 (10) | −0.0104 (9) |
C15 | 0.0780 (17) | 0.0515 (12) | 0.0792 (16) | −0.0100 (11) | −0.0187 (12) | −0.0076 (10) |
C16 | 0.066 (3) | 0.068 (3) | 0.090 (4) | −0.005 (2) | −0.009 (2) | −0.028 (3) |
C17 | 0.085 (3) | 0.078 (3) | 0.106 (3) | −0.025 (2) | −0.023 (2) | −0.018 (2) |
C16' | 0.103 (7) | 0.081 (6) | 0.059 (5) | −0.016 (5) | 0.006 (5) | −0.018 (4) |
C17' | 0.116 (9) | 0.102 (9) | 0.144 (10) | −0.019 (7) | 0.035 (8) | −0.007 (8) |
N1—N2 | 1.3878 (18) | C11—H11C | 0.9600 |
N1—C6 | 1.411 (2) | C12—C13 | 1.513 (2) |
N1—H1 | 0.8600 | C12—H12A | 0.9700 |
N2—C7 | 1.382 (2) | C12—H12B | 0.9700 |
N2—C9 | 1.403 (2) | C13—C14 | 1.510 (3) |
N3—C9 | 1.276 (2) | C13—H13A | 0.9700 |
N3—C8 | 1.494 (2) | C13—H13B | 0.9700 |
O1—C7 | 1.202 (2) | C14—C15 | 1.502 (3) |
S1—C9 | 1.7337 (16) | C14—H14A | 0.9700 |
S1—C12 | 1.8063 (19) | C14—H14B | 0.9700 |
C1—C2 | 1.381 (3) | C15—C16' | 1.497 (7) |
C1—C6 | 1.385 (2) | C15—C16 | 1.547 (4) |
C1—H1A | 0.9300 | C15—H15A | 0.9700 |
C2—C3 | 1.372 (3) | C15—H15B | 0.9700 |
C2—H2 | 0.9300 | C15—H15C | 0.9700 |
C3—C4 | 1.368 (4) | C15—H15D | 0.9700 |
C3—H3 | 0.9300 | C16—C17 | 1.506 (5) |
C4—C5 | 1.379 (3) | C16—H16A | 0.9700 |
C4—H4 | 0.9300 | C16—H16B | 0.9700 |
C5—C6 | 1.388 (3) | C17—H17A | 0.9600 |
C5—H5 | 0.9300 | C17—H17B | 0.9600 |
C7—C8 | 1.519 (2) | C17—H17C | 0.9600 |
C8—C10 | 1.520 (3) | C16'—C17' | 1.493 (8) |
C8—C11 | 1.527 (3) | C16'—H16C | 0.9700 |
C10—H10A | 0.9600 | C16'—H16D | 0.9700 |
C10—H10B | 0.9600 | C17'—H17D | 0.9600 |
C10—H10C | 0.9600 | C17'—H17E | 0.9600 |
C11—H11A | 0.9600 | C17'—H17F | 0.9600 |
C11—H11B | 0.9600 | ||
N2—N1—C6 | 117.06 (13) | S1—C12—H12B | 109.7 |
N2—N1—H1 | 121.5 | H12A—C12—H12B | 108.2 |
C6—N1—H1 | 121.5 | C14—C13—C12 | 112.16 (15) |
C7—N2—N1 | 127.29 (14) | C14—C13—H13A | 109.2 |
C7—N2—C9 | 108.89 (14) | C12—C13—H13A | 109.2 |
N1—N2—C9 | 123.64 (13) | C14—C13—H13B | 109.2 |
C9—N3—C8 | 106.38 (14) | C12—C13—H13B | 109.2 |
C9—S1—C12 | 100.18 (8) | H13A—C13—H13B | 107.9 |
C2—C1—C6 | 119.7 (2) | C15—C14—C13 | 115.09 (18) |
C2—C1—H1A | 120.1 | C15—C14—H14A | 108.5 |
C6—C1—H1A | 120.1 | C13—C14—H14A | 108.5 |
C3—C2—C1 | 121.4 (2) | C15—C14—H14B | 108.5 |
C3—C2—H2 | 119.3 | C13—C14—H14B | 108.5 |
C1—C2—H2 | 119.3 | H14A—C14—H14B | 107.5 |
C4—C3—C2 | 118.8 (2) | C16'—C15—C14 | 126.5 (6) |
C4—C3—H3 | 120.6 | C16'—C15—C16 | 25.6 (4) |
C2—C3—H3 | 120.6 | C14—C15—C16 | 109.6 (2) |
C3—C4—C5 | 120.9 (2) | C16'—C15—H15A | 113.6 |
C3—C4—H4 | 119.5 | C14—C15—H15A | 109.7 |
C5—C4—H4 | 119.5 | C16—C15—H15A | 109.7 |
C4—C5—C6 | 120.3 (2) | C16'—C15—H15B | 85.0 |
C4—C5—H5 | 119.8 | C14—C15—H15B | 109.7 |
C6—C5—H5 | 119.8 | C16—C15—H15B | 109.7 |
C1—C6—C5 | 118.79 (18) | H15A—C15—H15B | 108.2 |
C1—C6—N1 | 123.13 (17) | C16'—C15—H15C | 106.0 |
C5—C6—N1 | 118.02 (16) | C14—C15—H15C | 106.0 |
O1—C7—N2 | 125.69 (16) | C16—C15—H15C | 96.1 |
O1—C7—C8 | 129.81 (16) | H15A—C15—H15C | 17.5 |
N2—C7—C8 | 104.49 (14) | H15B—C15—H15C | 124.4 |
N3—C8—C7 | 105.20 (13) | C16'—C15—H15D | 104.6 |
N3—C8—C10 | 110.81 (17) | C14—C15—H15D | 106.0 |
C7—C8—C10 | 111.01 (17) | C16—C15—H15D | 130.2 |
N3—C8—C11 | 109.76 (16) | H15A—C15—H15D | 88.9 |
C7—C8—C11 | 107.78 (17) | H15B—C15—H15D | 23.2 |
C10—C8—C11 | 112.01 (19) | H15C—C15—H15D | 106.3 |
N3—C9—N2 | 114.94 (14) | C17—C16—C15 | 113.7 (3) |
N3—C9—S1 | 128.92 (13) | C17—C16—H16A | 108.8 |
N2—C9—S1 | 116.14 (12) | C15—C16—H16A | 108.8 |
C8—C10—H10A | 109.5 | C17—C16—H16B | 108.8 |
C8—C10—H10B | 109.5 | C15—C16—H16B | 108.8 |
H10A—C10—H10B | 109.5 | H16A—C16—H16B | 107.7 |
C8—C10—H10C | 109.5 | C17'—C16'—C15 | 97.8 (8) |
H10A—C10—H10C | 109.5 | C17'—C16'—H16C | 112.2 |
H10B—C10—H10C | 109.5 | C15—C16'—H16C | 112.2 |
C8—C11—H11A | 109.5 | C17'—C16'—H16D | 112.2 |
C8—C11—H11B | 109.5 | C15—C16'—H16D | 112.2 |
H11A—C11—H11B | 109.5 | H16C—C16'—H16D | 109.8 |
C8—C11—H11C | 109.5 | C16'—C17'—H17D | 109.5 |
H11A—C11—H11C | 109.5 | C16'—C17'—H17E | 109.5 |
H11B—C11—H11C | 109.5 | H17D—C17'—H17E | 109.5 |
C13—C12—S1 | 109.73 (13) | C16'—C17'—H17F | 109.5 |
C13—C12—H12A | 109.7 | H17D—C17'—H17F | 109.5 |
S1—C12—H12A | 109.7 | H17E—C17'—H17F | 109.5 |
C13—C12—H12B | 109.7 | ||
C6—N1—N2—C7 | 76.7 (2) | O1—C7—C8—C10 | 58.3 (3) |
C6—N1—N2—C9 | −97.85 (18) | N2—C7—C8—C10 | −122.80 (18) |
C6—C1—C2—C3 | −0.4 (3) | O1—C7—C8—C11 | −64.7 (3) |
C1—C2—C3—C4 | −0.1 (4) | N2—C7—C8—C11 | 114.19 (17) |
C2—C3—C4—C5 | 0.1 (4) | C8—N3—C9—N2 | 0.3 (2) |
C3—C4—C5—C6 | 0.4 (4) | C8—N3—C9—S1 | −179.96 (14) |
C2—C1—C6—C5 | 0.9 (3) | C7—N2—C9—N3 | −2.3 (2) |
C2—C1—C6—N1 | 178.00 (18) | N1—N2—C9—N3 | 173.08 (15) |
C4—C5—C6—C1 | −0.9 (3) | C7—N2—C9—S1 | 177.90 (12) |
C4—C5—C6—N1 | −178.14 (18) | N1—N2—C9—S1 | −6.7 (2) |
N2—N1—C6—C1 | 7.0 (2) | C12—S1—C9—N3 | 5.03 (19) |
N2—N1—C6—C5 | −175.88 (15) | C12—S1—C9—N2 | −175.25 (13) |
N1—N2—C7—O1 | 6.9 (3) | C9—S1—C12—C13 | 169.55 (14) |
C9—N2—C7—O1 | −177.93 (19) | S1—C12—C13—C14 | −179.94 (14) |
N1—N2—C7—C8 | −172.10 (15) | C12—C13—C14—C15 | −175.90 (19) |
C9—N2—C7—C8 | 3.10 (19) | C13—C14—C15—C16' | −162.4 (5) |
C9—N3—C8—C7 | 1.6 (2) | C13—C14—C15—C16 | 175.6 (3) |
C9—N3—C8—C10 | 121.66 (19) | C16'—C15—C16—C17 | 46.1 (12) |
C9—N3—C8—C11 | −114.11 (18) | C14—C15—C16—C17 | −178.1 (4) |
O1—C7—C8—N3 | 178.2 (2) | C14—C15—C16'—C17' | −89.9 (9) |
N2—C7—C8—N3 | −2.88 (19) | C16—C15—C16'—C17' | −35.1 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13B···O1i | 0.97 | 2.57 | 3.430 (2) | 148 |
N1—H1···N3ii | 0.86 | 2.60 | 3.189 (2) | 126 |
C11—H11A···O1iii | 0.96 | 2.34 | 3.299 (3) | 173 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C17H25N3OS |
Mr | 319.46 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 292 |
a, b, c (Å) | 6.2528 (5), 14.8770 (11), 19.1740 (15) |
β (°) | 93.806 (1) |
V (Å3) | 1779.7 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.964, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10984, 4037, 3099 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.157, 1.06 |
No. of reflections | 4037 |
No. of parameters | 222 |
No. of restraints | 16 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.49, −0.44 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13B···O1i | 0.97 | 2.57 | 3.430 (2) | 147.6 |
N1—H1···N3ii | 0.86 | 2.60 | 3.189 (2) | 126.4 |
C11—H11A···O1iii | 0.96 | 2.34 | 3.299 (3) | 172.6 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) x−1, y, z. |
Imidazolinones are important heterocycles exhibiting remarkable biological activities, especially fungicidal activities (Khodair et al., 1998). Since a novel mitochondrial respiratory inhibitor (Fenamidone) was found to show high fungicidal activities, many other 2-alkylthio imidazolinones have been synthesized to evaluate their fungicidal activities (Bruhn et al., 1998). We obtained the title compound, (I), which may be used as a new precursor for obtaining bioactive molecules. The crystal structure of (I) is presented here.
Atom S1, N1 and the five-membered imidazolone ring are essentially planar. The C16 and C17 atoms, and the hydrogen atoms attached to C15, C16 and C17 are disordered over two sites, with refined occupancies of 0.309 (7) and 0.691 (7) (Fig. 1). The bond lengths involving atom C9 indicate a degree of electron delocalization (Yuan et al., 2006). As can be seen from the packing diagram (Fig. 2), intermolecular N—H···N and C—H···O hydrogen bondings (Table 1) link the molecules.