organic compounds
1-(4-Methoxyphenylsulfonyl)-5-methyl-5-phenylimidazolidine-2,4-dione
aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, and bInstitute of Physics, University of Neuchâtel, rue Emile-Argand 11, CH-2009 Neuchâtel, Switzerland
*Correspondence e-mail: shameed@qau.edu.pk
The title compound, C17H16N2O5S, crystallized in the chiral monoclinic P21, with two enantiomeric molecules (A and B) in the It is composed of a methylimidazolidine-2,4-dione unit substituted with a phenyl group and a 4-methoxyphenylsulfonyl group. The benzene ring mean planes are inclined to one another by 22.20 (14)° in molecule A and by 15.82 (13)° in molecule B. In the the A and B molecules are linked by N—H⋯O hydrogen bonds, forming centrosymmetric dimers. A number of C—H⋯O interactions are also present in the leading to the formation of a three-dimensinoal network.
Related literature
For the applications of immidazolidine-2,4-diones, see: Thenmozhiyal et al. (2004); Zhang et al. (2004). For the activity of sulfonylimmidazolidine-2,4-diones, see: Kashif, Ahmad & Hameed (2008); Ahmad et al. (2000, 2002); Murakami et al. (1997). For related crystal structures, see: Hussain et al. (2009); Kashif, Hussain et al. (2008).
Experimental
Crystal data
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Data collection
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Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000); cell CELL in IPDS-I; data reduction: INTEGRATE in IPDS-I; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536809016092/bt2941sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809016092/bt2941Isup2.hkl
5-Methyl-5-phenylimidazolidine-2,4-dione (4.8 mmol) in CH2Cl2 was stirred with triethyl amine (4.8 mmol) and catalytic amounts of DMAP. 4-Methoxybenzene sulfonyl chloride (5.8 mmol) in CH2Cl2 was added dropwise. The reaction mixture was stirred continually at 298 K until the reaction was complete (monitored by TLC). The reaction mixture was then diluted with 1 N HCl and extracted with CH2Cl2 (3 × 25 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in ethyl acetate afforded colourless rod-like crystals of the title compound, suitable for X-ray analysis.
The NH H-atoms were located in difference Fourier maps and freely refined. The H-atoms bonded to C were included in calculated positions [C—H = 0.95 - 0.98 Å] and treated as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).
Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000); cell
CELL in IPDS-I (Stoe & Cie, 2000); data reduction: INTEGRATE in IPDS-I (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. A view of the molecular structure of the two indepenent molecules of the title compound. Displacement ellipsoids are drawn at the 50% probabiltiy level. | |
Fig. 2. An auto-fit view (Spek, 2009) of the two independent molecules (A black; B red) in the title compound. | |
Fig. 3. A view along the a axis of the crystal packing in the title compound, showing the N—H···O hydrogen bonds which link the two independent molecules (A and B) to form a dimer-like arrangement (see Table 1 for details). | |
Fig. 4. A perspective view along the a axis of the crystal packing in the title compound showing the N—H···O and C—H···O hydrogen bonds, which link the molecules to form a three-dimensional network (see Table 1 for details). |
C17H16N2O5S | F(000) = 752 |
Mr = 360.38 | Dx = 1.421 Mg m−3 |
Monoclinic, P21 | Melting point = 471–473 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2314 (6) Å | Cell parameters from 8000 reflections |
b = 17.5694 (12) Å | θ = 2.6–26.0° |
c = 15.5892 (16) Å | µ = 0.22 mm−1 |
β = 99.373 (12)° | T = 173 K |
V = 1683.9 (3) Å3 | Rod, colourless |
Z = 4 | 0.38 × 0.30 × 0.19 mm |
Stoe IPDS diffractometer | 4309 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 26.1°, θmin = 2.7° |
ϕ rotation scans | h = −7→7 |
13521 measured reflections | k = −20→21 |
6394 independent reflections | l = −19→19 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.029 | w = 1/[σ2(Fo2) + (0.024P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.058 | (Δ/σ)max = 0.001 |
S = 0.81 | Δρmax = 0.17 e Å−3 |
6394 reflections | Δρmin = −0.20 e Å−3 |
465 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.0042 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 2987 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.06 (5) |
C17H16N2O5S | V = 1683.9 (3) Å3 |
Mr = 360.38 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.2314 (6) Å | µ = 0.22 mm−1 |
b = 17.5694 (12) Å | T = 173 K |
c = 15.5892 (16) Å | 0.38 × 0.30 × 0.19 mm |
β = 99.373 (12)° |
Stoe IPDS diffractometer | 4309 reflections with I > 2σ(I) |
13521 measured reflections | Rint = 0.033 |
6394 independent reflections |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.058 | Δρmax = 0.17 e Å−3 |
S = 0.81 | Δρmin = −0.20 e Å−3 |
6394 reflections | Absolute structure: Flack (1983), 2987 Friedel pairs |
465 parameters | Absolute structure parameter: 0.06 (5) |
3 restraints |
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 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 | 0.49288 (9) | 0.27479 (4) | 0.41621 (4) | 0.0322 (2) | |
O1 | 0.5317 (3) | 0.19861 (10) | 0.39102 (11) | 0.0374 (6) | |
O2 | 0.6619 (3) | 0.33014 (11) | 0.42511 (11) | 0.0414 (6) | |
O3 | 0.0791 (3) | 0.20334 (11) | 0.32063 (11) | 0.0388 (6) | |
O4 | −0.0034 (3) | 0.43832 (11) | 0.19756 (12) | 0.0497 (7) | |
O5 | 0.0979 (3) | 0.26824 (12) | 0.73090 (12) | 0.0622 (8) | |
N1 | 0.3022 (3) | 0.30995 (11) | 0.33861 (12) | 0.0273 (7) | |
N2 | −0.0122 (3) | 0.31655 (12) | 0.24927 (13) | 0.0340 (8) | |
C1 | 0.1190 (4) | 0.26883 (16) | 0.30444 (15) | 0.0299 (8) | |
C2 | 0.0728 (4) | 0.38756 (16) | 0.24475 (17) | 0.0330 (9) | |
C3 | 0.2862 (4) | 0.39125 (14) | 0.30845 (15) | 0.0285 (8) | |
C4 | 0.2584 (4) | 0.44517 (15) | 0.38246 (15) | 0.0289 (8) | |
C5 | 0.0795 (4) | 0.43753 (17) | 0.42345 (17) | 0.0409 (10) | |
C6 | 0.0477 (5) | 0.48556 (18) | 0.49017 (19) | 0.0480 (10) | |
C7 | 0.1927 (5) | 0.54235 (18) | 0.51559 (19) | 0.0519 (11) | |
C8 | 0.3705 (6) | 0.55014 (19) | 0.4763 (2) | 0.0616 (11) | |
C9 | 0.4043 (5) | 0.50230 (18) | 0.40945 (18) | 0.0483 (10) | |
C10 | 0.4663 (4) | 0.41178 (16) | 0.25751 (18) | 0.0419 (10) | |
C11 | 0.3765 (4) | 0.27369 (15) | 0.51029 (15) | 0.0303 (8) | |
C12 | 0.4167 (4) | 0.33274 (15) | 0.56842 (16) | 0.0395 (9) | |
C13 | 0.3248 (5) | 0.33334 (16) | 0.64261 (17) | 0.0447 (10) | |
C14 | 0.1936 (4) | 0.27364 (18) | 0.65885 (16) | 0.0438 (10) | |
C15 | 0.1345 (7) | 0.32823 (19) | 0.7938 (2) | 0.0826 (16) | |
C16 | 0.1511 (4) | 0.21413 (17) | 0.60013 (18) | 0.0453 (10) | |
C17 | 0.2418 (4) | 0.21460 (15) | 0.52550 (16) | 0.0360 (9) | |
S2 | 0.17941 (9) | 0.16666 (4) | 0.07688 (4) | 0.0343 (2) | |
O6 | 0.1557 (3) | 0.24522 (10) | 0.09316 (11) | 0.0443 (7) | |
O7 | 0.0040 (3) | 0.11541 (11) | 0.07948 (12) | 0.0434 (6) | |
O8 | 0.5996 (3) | 0.24274 (10) | 0.16846 (11) | 0.0382 (6) | |
O9 | 0.7248 (3) | 0.00425 (10) | 0.27716 (11) | 0.0390 (6) | |
O10 | 0.5175 (3) | 0.11964 (11) | −0.24698 (12) | 0.0523 (7) | |
N3 | 0.3788 (3) | 0.13476 (12) | 0.15370 (13) | 0.0285 (7) | |
N4 | 0.7059 (3) | 0.12965 (12) | 0.23550 (12) | 0.0295 (7) | |
C18 | 0.5652 (4) | 0.17648 (16) | 0.18420 (15) | 0.0290 (8) | |
C19 | 0.6295 (4) | 0.05719 (16) | 0.23806 (15) | 0.0300 (8) | |
C20 | 0.4033 (4) | 0.05427 (15) | 0.18445 (15) | 0.0286 (8) | |
C21 | 0.4028 (4) | −0.00248 (14) | 0.10977 (15) | 0.0284 (8) | |
C22 | 0.5752 (4) | −0.00181 (16) | 0.06382 (15) | 0.0354 (9) | |
C23 | 0.5797 (4) | −0.05236 (18) | −0.00387 (17) | 0.0442 (10) | |
C24 | 0.4127 (5) | −0.10347 (16) | −0.02589 (17) | 0.0466 (10) | |
C25 | 0.2398 (5) | −0.10367 (18) | 0.01867 (19) | 0.0488 (11) | |
C26 | 0.2350 (4) | −0.05315 (16) | 0.08642 (17) | 0.0390 (9) | |
C27 | 0.2452 (5) | 0.03531 (17) | 0.24687 (19) | 0.0424 (10) | |
C28 | 0.2780 (4) | 0.15486 (15) | −0.02036 (16) | 0.0318 (8) | |
C29 | 0.1934 (4) | 0.09875 (15) | −0.07862 (16) | 0.0338 (8) | |
C30 | 0.2755 (4) | 0.08912 (15) | −0.15410 (16) | 0.0366 (9) | |
C31 | 0.4463 (4) | 0.13473 (15) | −0.17102 (16) | 0.0375 (9) | |
C32 | 0.6969 (5) | 0.1640 (2) | −0.26728 (19) | 0.0633 (13) | |
C33 | 0.5329 (4) | 0.18981 (17) | −0.11248 (17) | 0.0487 (10) | |
C34 | 0.4462 (4) | 0.19955 (17) | −0.03783 (17) | 0.0453 (10) | |
H2N | −0.143 (3) | 0.2979 (16) | 0.2234 (17) | 0.057 (9)* | |
H5 | −0.02360 | 0.39850 | 0.40540 | 0.0490* | |
H6 | −0.07520 | 0.47900 | 0.51840 | 0.0580* | |
H7 | 0.16960 | 0.57630 | 0.56060 | 0.0620* | |
H8 | 0.47330 | 0.58910 | 0.49500 | 0.0740* | |
H9 | 0.52860 | 0.50890 | 0.38210 | 0.0580* | |
H10A | 0.47220 | 0.37370 | 0.21200 | 0.0630* | |
H10B | 0.60600 | 0.41290 | 0.29690 | 0.0630* | |
H10C | 0.43690 | 0.46200 | 0.23070 | 0.0630* | |
H12 | 0.50880 | 0.37340 | 0.55720 | 0.0470* | |
H13 | 0.35120 | 0.37450 | 0.68240 | 0.0540* | |
H15A | 0.29050 | 0.33220 | 0.81610 | 0.1240* | |
H15B | 0.08230 | 0.37640 | 0.76630 | 0.1240* | |
H15C | 0.05580 | 0.31710 | 0.84180 | 0.1240* | |
H16 | 0.05990 | 0.17330 | 0.61140 | 0.0540* | |
H17 | 0.21190 | 0.17440 | 0.48450 | 0.0430* | |
H4N | 0.835 (3) | 0.1490 (15) | 0.2635 (16) | 0.053 (9)* | |
H22 | 0.69070 | 0.03350 | 0.07890 | 0.0420* | |
H23 | 0.69830 | −0.05180 | −0.03520 | 0.0530* | |
H24 | 0.41700 | −0.13860 | −0.07190 | 0.0560* | |
H25 | 0.12350 | −0.13850 | 0.00300 | 0.0590* | |
H26 | 0.11500 | −0.05340 | 0.11700 | 0.0470* | |
H27A | 0.09600 | 0.03590 | 0.21510 | 0.0640* | |
H27B | 0.25970 | 0.07320 | 0.29360 | 0.0640* | |
H27C | 0.27880 | −0.01530 | 0.27190 | 0.0640* | |
H29 | 0.07880 | 0.06710 | −0.06620 | 0.0410* | |
H30 | 0.21600 | 0.05140 | −0.19480 | 0.0440* | |
H32A | 0.82400 | 0.15630 | −0.22210 | 0.0950* | |
H32B | 0.65720 | 0.21800 | −0.27000 | 0.0950* | |
H32C | 0.73170 | 0.14780 | −0.32360 | 0.0950* | |
H33 | 0.65070 | 0.22050 | −0.12370 | 0.0580* | |
H34 | 0.50350 | 0.23790 | 0.00250 | 0.0540* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0318 (3) | 0.0308 (4) | 0.0350 (3) | 0.0037 (3) | 0.0081 (3) | 0.0046 (3) |
O1 | 0.0456 (10) | 0.0279 (11) | 0.0406 (10) | 0.0154 (8) | 0.0127 (8) | 0.0030 (8) |
O2 | 0.0309 (9) | 0.0458 (13) | 0.0475 (11) | −0.0090 (9) | 0.0062 (8) | 0.0103 (10) |
O3 | 0.0469 (10) | 0.0229 (12) | 0.0444 (11) | −0.0020 (8) | 0.0006 (8) | −0.0035 (9) |
O4 | 0.0650 (12) | 0.0332 (12) | 0.0448 (11) | 0.0118 (10) | −0.0093 (9) | 0.0037 (10) |
O5 | 0.0954 (15) | 0.0495 (14) | 0.0531 (12) | 0.0007 (12) | 0.0464 (11) | −0.0022 (11) |
N1 | 0.0297 (10) | 0.0221 (13) | 0.0300 (11) | 0.0007 (8) | 0.0046 (9) | −0.0009 (9) |
N2 | 0.0392 (13) | 0.0240 (14) | 0.0355 (12) | 0.0028 (10) | −0.0037 (10) | −0.0047 (10) |
C1 | 0.0356 (13) | 0.0231 (16) | 0.0305 (13) | 0.0035 (13) | 0.0038 (10) | −0.0040 (12) |
C2 | 0.0422 (15) | 0.0260 (17) | 0.0308 (15) | 0.0074 (12) | 0.0060 (12) | −0.0041 (12) |
C3 | 0.0352 (13) | 0.0192 (15) | 0.0315 (14) | 0.0022 (10) | 0.0068 (11) | 0.0020 (11) |
C4 | 0.0350 (13) | 0.0224 (15) | 0.0289 (13) | 0.0001 (11) | 0.0043 (11) | 0.0009 (11) |
C5 | 0.0381 (15) | 0.0392 (19) | 0.0462 (17) | −0.0060 (13) | 0.0092 (13) | −0.0137 (14) |
C6 | 0.0500 (17) | 0.055 (2) | 0.0410 (16) | 0.0091 (15) | 0.0136 (13) | −0.0104 (14) |
C7 | 0.083 (2) | 0.035 (2) | 0.0374 (16) | 0.0077 (16) | 0.0091 (16) | −0.0062 (14) |
C8 | 0.091 (2) | 0.046 (2) | 0.0474 (19) | −0.0311 (18) | 0.0097 (18) | −0.0166 (16) |
C9 | 0.0581 (17) | 0.041 (2) | 0.0479 (17) | −0.0172 (15) | 0.0152 (14) | −0.0016 (15) |
C10 | 0.0473 (16) | 0.0388 (19) | 0.0435 (16) | 0.0055 (13) | 0.0187 (13) | 0.0089 (13) |
C11 | 0.0329 (12) | 0.0241 (15) | 0.0346 (13) | −0.0004 (12) | 0.0078 (10) | 0.0022 (12) |
C12 | 0.0529 (16) | 0.0253 (17) | 0.0408 (15) | −0.0063 (12) | 0.0091 (13) | 0.0031 (13) |
C13 | 0.0721 (19) | 0.0257 (17) | 0.0390 (15) | −0.0021 (14) | 0.0175 (14) | −0.0040 (12) |
C14 | 0.0571 (17) | 0.0390 (18) | 0.0404 (15) | 0.0067 (15) | 0.0234 (13) | 0.0032 (14) |
C15 | 0.154 (4) | 0.048 (2) | 0.060 (2) | 0.012 (2) | 0.060 (2) | −0.0070 (18) |
C16 | 0.0553 (17) | 0.0359 (19) | 0.0496 (17) | −0.0069 (13) | 0.0235 (13) | −0.0008 (14) |
C17 | 0.0407 (14) | 0.0306 (17) | 0.0384 (14) | −0.0018 (12) | 0.0117 (11) | −0.0037 (12) |
S2 | 0.0317 (3) | 0.0336 (4) | 0.0382 (4) | 0.0030 (3) | 0.0073 (3) | −0.0010 (3) |
O6 | 0.0518 (11) | 0.0318 (13) | 0.0487 (11) | 0.0145 (9) | 0.0062 (9) | −0.0040 (9) |
O7 | 0.0269 (9) | 0.0545 (13) | 0.0501 (11) | −0.0038 (9) | 0.0101 (8) | 0.0012 (10) |
O8 | 0.0482 (10) | 0.0232 (12) | 0.0417 (11) | −0.0054 (8) | 0.0026 (8) | −0.0007 (8) |
O9 | 0.0500 (10) | 0.0287 (12) | 0.0367 (10) | 0.0005 (9) | 0.0024 (8) | 0.0032 (9) |
O10 | 0.0612 (12) | 0.0570 (15) | 0.0427 (11) | −0.0077 (10) | 0.0202 (9) | −0.0060 (10) |
N3 | 0.0325 (10) | 0.0199 (13) | 0.0335 (11) | −0.0013 (8) | 0.0064 (9) | −0.0012 (9) |
N4 | 0.0337 (12) | 0.0226 (13) | 0.0320 (12) | −0.0019 (10) | 0.0050 (9) | −0.0015 (9) |
C18 | 0.0330 (13) | 0.0269 (17) | 0.0284 (13) | 0.0023 (12) | 0.0085 (10) | −0.0048 (12) |
C19 | 0.0430 (15) | 0.0258 (16) | 0.0231 (13) | −0.0004 (12) | 0.0109 (11) | −0.0014 (11) |
C20 | 0.0325 (13) | 0.0228 (15) | 0.0325 (14) | −0.0023 (10) | 0.0114 (11) | −0.0041 (11) |
C21 | 0.0323 (13) | 0.0204 (15) | 0.0324 (14) | −0.0014 (11) | 0.0050 (11) | −0.0017 (11) |
C22 | 0.0345 (13) | 0.0394 (18) | 0.0334 (14) | −0.0009 (12) | 0.0090 (11) | −0.0068 (12) |
C23 | 0.0547 (17) | 0.0437 (19) | 0.0353 (15) | 0.0077 (15) | 0.0105 (13) | −0.0057 (14) |
C24 | 0.077 (2) | 0.0272 (18) | 0.0341 (15) | 0.0070 (15) | 0.0050 (15) | −0.0063 (13) |
C25 | 0.0674 (19) | 0.0307 (19) | 0.0450 (17) | −0.0152 (14) | −0.0007 (15) | −0.0053 (14) |
C26 | 0.0448 (15) | 0.0308 (17) | 0.0421 (16) | −0.0109 (13) | 0.0088 (12) | −0.0017 (13) |
C27 | 0.0479 (16) | 0.0352 (19) | 0.0494 (18) | −0.0030 (13) | 0.0242 (14) | −0.0004 (13) |
C28 | 0.0326 (12) | 0.0291 (16) | 0.0331 (13) | 0.0000 (11) | 0.0037 (10) | 0.0007 (11) |
C29 | 0.0328 (13) | 0.0308 (16) | 0.0371 (14) | −0.0056 (11) | 0.0033 (11) | 0.0006 (12) |
C30 | 0.0426 (15) | 0.0297 (17) | 0.0360 (15) | −0.0056 (12) | 0.0023 (12) | −0.0042 (12) |
C31 | 0.0429 (14) | 0.0403 (18) | 0.0303 (14) | −0.0028 (13) | 0.0088 (11) | 0.0005 (12) |
C32 | 0.0559 (18) | 0.088 (3) | 0.0501 (17) | −0.0130 (19) | 0.0212 (14) | 0.0026 (18) |
C33 | 0.0520 (16) | 0.055 (2) | 0.0409 (16) | −0.0264 (14) | 0.0131 (13) | −0.0059 (14) |
C34 | 0.0553 (17) | 0.0441 (19) | 0.0362 (15) | −0.0192 (14) | 0.0069 (13) | −0.0085 (13) |
S1—O1 | 1.4266 (19) | C7—H7 | 0.9500 |
S1—O2 | 1.424 (2) | C8—H8 | 0.9500 |
S1—N1 | 1.670 (2) | C9—H9 | 0.9500 |
S1—C11 | 1.739 (2) | C10—H10B | 0.9800 |
S2—N3 | 1.676 (2) | C10—H10A | 0.9800 |
S2—O6 | 1.4155 (19) | C10—H10C | 0.9800 |
S2—O7 | 1.422 (2) | C12—H12 | 0.9500 |
S2—C28 | 1.738 (3) | C13—H13 | 0.9500 |
O3—C1 | 1.212 (3) | C15—H15B | 0.9800 |
O4—C2 | 1.203 (3) | C15—H15A | 0.9800 |
O5—C14 | 1.358 (3) | C15—H15C | 0.9800 |
O5—C15 | 1.432 (4) | C16—H16 | 0.9500 |
O8—C18 | 1.216 (3) | C17—H17 | 0.9500 |
O9—C19 | 1.213 (3) | C19—C20 | 1.518 (3) |
O10—C31 | 1.357 (3) | C20—C27 | 1.530 (4) |
O10—C32 | 1.440 (4) | C20—C21 | 1.532 (3) |
N1—C1 | 1.382 (3) | C21—C22 | 1.385 (3) |
N1—C3 | 1.502 (3) | C21—C26 | 1.376 (4) |
N2—C1 | 1.372 (3) | C22—C23 | 1.383 (4) |
N2—C2 | 1.362 (3) | C23—C24 | 1.375 (4) |
N2—H2N | 0.91 (2) | C24—C25 | 1.374 (4) |
N3—C20 | 1.493 (3) | C25—C26 | 1.384 (4) |
N3—C18 | 1.390 (3) | C28—C34 | 1.372 (4) |
N4—C18 | 1.363 (3) | C28—C29 | 1.385 (4) |
N4—C19 | 1.362 (3) | C29—C30 | 1.368 (4) |
N4—H4N | 0.92 (2) | C30—C31 | 1.391 (4) |
C2—C3 | 1.526 (4) | C31—C33 | 1.378 (4) |
C3—C4 | 1.524 (3) | C33—C34 | 1.371 (4) |
C3—C10 | 1.520 (4) | C22—H22 | 0.9500 |
C4—C9 | 1.374 (4) | C23—H23 | 0.9500 |
C4—C5 | 1.379 (4) | C24—H24 | 0.9500 |
C5—C6 | 1.379 (4) | C25—H25 | 0.9500 |
C6—C7 | 1.361 (4) | C26—H26 | 0.9500 |
C7—C8 | 1.357 (5) | C27—H27A | 0.9800 |
C8—C9 | 1.381 (4) | C27—H27B | 0.9800 |
C11—C17 | 1.380 (4) | C27—H27C | 0.9800 |
C11—C12 | 1.373 (4) | C29—H29 | 0.9500 |
C12—C13 | 1.372 (4) | C30—H30 | 0.9500 |
C13—C14 | 1.378 (4) | C32—H32A | 0.9800 |
C14—C16 | 1.387 (4) | C32—H32B | 0.9800 |
C16—C17 | 1.374 (4) | C32—H32C | 0.9800 |
C5—H5 | 0.9500 | C33—H33 | 0.9500 |
C6—H6 | 0.9500 | C34—H34 | 0.9500 |
O1—S1—O2 | 120.78 (12) | C13—C12—H12 | 120.00 |
O1—S1—N1 | 106.27 (10) | C14—C13—H13 | 120.00 |
O1—S1—C11 | 109.54 (12) | C12—C13—H13 | 120.00 |
O2—S1—N1 | 104.23 (11) | O5—C15—H15B | 109.00 |
O2—S1—C11 | 109.21 (12) | O5—C15—H15A | 109.00 |
N1—S1—C11 | 105.65 (11) | H15A—C15—H15B | 109.00 |
O7—S2—N3 | 104.59 (11) | H15A—C15—H15C | 110.00 |
O7—S2—C28 | 109.38 (12) | O5—C15—H15C | 109.00 |
N3—S2—C28 | 104.90 (11) | H15B—C15—H15C | 110.00 |
O6—S2—C28 | 109.55 (12) | C14—C16—H16 | 120.00 |
O6—S2—O7 | 120.61 (12) | C17—C16—H16 | 120.00 |
O6—S2—N3 | 106.56 (11) | C16—C17—H17 | 120.00 |
C14—O5—C15 | 118.2 (2) | C11—C17—H17 | 120.00 |
C31—O10—C32 | 117.5 (2) | N3—C18—N4 | 107.7 (2) |
S1—N1—C1 | 122.10 (17) | O8—C18—N3 | 126.9 (2) |
S1—N1—C3 | 125.57 (16) | O8—C18—N4 | 125.4 (2) |
C1—N1—C3 | 111.58 (19) | O9—C19—C20 | 125.8 (2) |
C1—N2—C2 | 113.3 (2) | O9—C19—N4 | 125.9 (2) |
C2—N2—H2N | 129.4 (18) | N4—C19—C20 | 108.3 (2) |
C1—N2—H2N | 117.2 (18) | N3—C20—C21 | 112.64 (19) |
S2—N3—C18 | 123.31 (18) | N3—C20—C19 | 100.5 (2) |
S2—N3—C20 | 124.85 (16) | C19—C20—C27 | 107.1 (2) |
C18—N3—C20 | 110.71 (19) | C21—C20—C27 | 114.8 (2) |
C18—N4—C19 | 112.8 (2) | N3—C20—C27 | 111.6 (2) |
C18—N4—H4N | 119.1 (16) | C19—C20—C21 | 109.1 (2) |
C19—N4—H4N | 128.1 (16) | C22—C21—C26 | 119.3 (2) |
N1—C1—N2 | 107.0 (2) | C20—C21—C22 | 118.8 (2) |
O3—C1—N1 | 126.9 (2) | C20—C21—C26 | 122.0 (2) |
O3—C1—N2 | 126.1 (2) | C21—C22—C23 | 120.2 (2) |
O4—C2—C3 | 125.6 (2) | C22—C23—C24 | 120.1 (2) |
O4—C2—N2 | 126.3 (2) | C23—C24—C25 | 120.0 (3) |
N2—C2—C3 | 108.1 (2) | C24—C25—C26 | 120.0 (3) |
N1—C3—C10 | 111.9 (2) | C21—C26—C25 | 120.5 (2) |
N1—C3—C4 | 111.35 (19) | C29—C28—C34 | 119.9 (2) |
N1—C3—C2 | 99.77 (19) | S2—C28—C29 | 120.4 (2) |
C2—C3—C4 | 108.9 (2) | S2—C28—C34 | 119.7 (2) |
C2—C3—C10 | 108.0 (2) | C28—C29—C30 | 119.8 (2) |
C4—C3—C10 | 115.6 (2) | C29—C30—C31 | 119.8 (2) |
C5—C4—C9 | 118.3 (2) | O10—C31—C33 | 124.5 (2) |
C3—C4—C9 | 122.3 (2) | O10—C31—C30 | 115.0 (2) |
C3—C4—C5 | 119.4 (2) | C30—C31—C33 | 120.5 (2) |
C4—C5—C6 | 121.1 (3) | C31—C33—C34 | 118.9 (2) |
C5—C6—C7 | 119.9 (3) | C28—C34—C33 | 121.1 (3) |
C6—C7—C8 | 119.6 (3) | C21—C22—H22 | 120.00 |
C7—C8—C9 | 121.0 (3) | C23—C22—H22 | 120.00 |
C4—C9—C8 | 120.1 (3) | C22—C23—H23 | 120.00 |
S1—C11—C17 | 120.15 (19) | C24—C23—H23 | 120.00 |
S1—C11—C12 | 119.5 (2) | C23—C24—H24 | 120.00 |
C12—C11—C17 | 120.4 (2) | C25—C24—H24 | 120.00 |
C11—C12—C13 | 120.4 (2) | C24—C25—H25 | 120.00 |
C12—C13—C14 | 119.4 (3) | C26—C25—H25 | 120.00 |
O5—C14—C16 | 115.5 (3) | C21—C26—H26 | 120.00 |
C13—C14—C16 | 120.5 (2) | C25—C26—H26 | 120.00 |
O5—C14—C13 | 124.0 (3) | C20—C27—H27A | 109.00 |
C14—C16—C17 | 119.6 (3) | C20—C27—H27B | 110.00 |
C11—C17—C16 | 119.7 (2) | C20—C27—H27C | 109.00 |
C4—C5—H5 | 119.00 | H27A—C27—H27B | 109.00 |
C6—C5—H5 | 119.00 | H27A—C27—H27C | 110.00 |
C5—C6—H6 | 120.00 | H27B—C27—H27C | 109.00 |
C7—C6—H6 | 120.00 | C28—C29—H29 | 120.00 |
C6—C7—H7 | 120.00 | C30—C29—H29 | 120.00 |
C8—C7—H7 | 120.00 | C29—C30—H30 | 120.00 |
C7—C8—H8 | 120.00 | C31—C30—H30 | 120.00 |
C9—C8—H8 | 119.00 | O10—C32—H32A | 109.00 |
C4—C9—H9 | 120.00 | O10—C32—H32B | 110.00 |
C8—C9—H9 | 120.00 | O10—C32—H32C | 109.00 |
H10A—C10—H10B | 109.00 | H32A—C32—H32B | 109.00 |
H10A—C10—H10C | 109.00 | H32A—C32—H32C | 109.00 |
C3—C10—H10C | 109.00 | H32B—C32—H32C | 109.00 |
C3—C10—H10B | 109.00 | C31—C33—H33 | 121.00 |
C3—C10—H10A | 110.00 | C34—C33—H33 | 121.00 |
H10B—C10—H10C | 110.00 | C28—C34—H34 | 119.00 |
C11—C12—H12 | 120.00 | C33—C34—H34 | 119.00 |
O1—S1—N1—C1 | 44.6 (2) | N2—C2—C3—N1 | 4.8 (2) |
O1—S1—N1—C3 | −146.18 (18) | O4—C2—C3—N1 | −173.7 (2) |
O2—S1—N1—C1 | 173.23 (18) | O4—C2—C3—C4 | 69.6 (3) |
O2—S1—N1—C3 | −17.6 (2) | O4—C2—C3—C10 | −56.8 (3) |
C11—S1—N1—C1 | −71.7 (2) | C10—C3—C4—C9 | −8.8 (4) |
C11—S1—N1—C3 | 97.5 (2) | N1—C3—C4—C9 | 120.3 (3) |
O1—S1—C11—C12 | 149.2 (2) | C2—C3—C4—C5 | 48.5 (3) |
O1—S1—C11—C17 | −31.9 (2) | N1—C3—C4—C5 | −60.6 (3) |
O2—S1—C11—C12 | 14.9 (2) | C10—C3—C4—C5 | 170.3 (2) |
O2—S1—C11—C17 | −166.3 (2) | C2—C3—C4—C9 | −130.6 (3) |
N1—S1—C11—C12 | −96.7 (2) | C9—C4—C5—C6 | −0.4 (4) |
N1—S1—C11—C17 | 82.2 (2) | C3—C4—C5—C6 | −179.5 (2) |
O6—S2—N3—C18 | −38.6 (2) | C3—C4—C9—C8 | 179.4 (3) |
O6—S2—N3—C20 | 154.74 (18) | C5—C4—C9—C8 | 0.3 (4) |
O7—S2—N3—C18 | −167.37 (19) | C4—C5—C6—C7 | 1.0 (4) |
O7—S2—N3—C20 | 26.0 (2) | C5—C6—C7—C8 | −1.5 (5) |
C28—S2—N3—C18 | 77.5 (2) | C6—C7—C8—C9 | 1.5 (5) |
C28—S2—N3—C20 | −89.1 (2) | C7—C8—C9—C4 | −0.8 (5) |
O6—S2—C28—C29 | −137.8 (2) | S1—C11—C12—C13 | 179.4 (2) |
O6—S2—C28—C34 | 44.6 (3) | C17—C11—C12—C13 | 0.5 (4) |
O7—S2—C28—C29 | −3.6 (3) | S1—C11—C17—C16 | 179.8 (2) |
O7—S2—C28—C34 | 178.9 (2) | C12—C11—C17—C16 | −1.4 (4) |
N3—S2—C28—C29 | 108.1 (2) | C11—C12—C13—C14 | 0.8 (4) |
N3—S2—C28—C34 | −69.4 (2) | C12—C13—C14—O5 | 178.9 (3) |
C15—O5—C14—C13 | 0.2 (4) | C12—C13—C14—C16 | −1.2 (4) |
C15—O5—C14—C16 | −179.6 (3) | O5—C14—C16—C17 | −179.7 (2) |
C32—O10—C31—C30 | −178.8 (2) | C13—C14—C16—C17 | 0.4 (4) |
C32—O10—C31—C33 | 0.5 (4) | C14—C16—C17—C11 | 0.9 (4) |
S1—N1—C3—C2 | −175.22 (16) | O9—C19—C20—N3 | −179.8 (2) |
S1—N1—C1—O3 | −5.0 (4) | O9—C19—C20—C21 | −61.3 (3) |
S1—N1—C1—N2 | 174.13 (15) | O9—C19—C20—C27 | 63.6 (3) |
C3—N1—C1—O3 | −175.6 (2) | N4—C19—C20—N3 | 0.9 (2) |
C3—N1—C1—N2 | 3.6 (3) | N4—C19—C20—C21 | 119.4 (2) |
C1—N1—C3—C2 | −5.0 (2) | N4—C19—C20—C27 | −115.8 (2) |
S1—N1—C3—C4 | −60.3 (3) | N3—C20—C21—C22 | 67.3 (3) |
S1—N1—C3—C10 | 70.7 (2) | N3—C20—C21—C26 | −111.8 (3) |
C1—N1—C3—C4 | 109.9 (2) | C19—C20—C21—C22 | −43.4 (3) |
C1—N1—C3—C10 | −119.1 (2) | C19—C20—C21—C26 | 137.6 (2) |
C1—N2—C2—O4 | 175.3 (3) | C27—C20—C21—C22 | −163.5 (2) |
C2—N2—C1—O3 | 179.0 (2) | C27—C20—C21—C26 | 17.4 (3) |
C2—N2—C1—N1 | −0.2 (3) | C20—C21—C22—C23 | 179.9 (2) |
C1—N2—C2—C3 | −3.2 (3) | C26—C21—C22—C23 | −1.0 (4) |
S2—N3—C18—O8 | 9.1 (4) | C20—C21—C26—C25 | −180.0 (3) |
S2—N3—C18—N4 | −170.73 (16) | C22—C21—C26—C25 | 1.0 (4) |
C20—N3—C18—N4 | −2.4 (3) | C21—C22—C23—C24 | 0.1 (4) |
S2—N3—C20—C19 | 169.04 (16) | C22—C23—C24—C25 | 0.8 (4) |
S2—N3—C20—C21 | 53.1 (3) | C23—C24—C25—C26 | −0.9 (4) |
S2—N3—C20—C27 | −77.7 (2) | C24—C25—C26—C21 | −0.1 (4) |
C18—N3—C20—C19 | 0.9 (2) | S2—C28—C29—C30 | −178.7 (2) |
C18—N3—C20—C21 | −115.0 (2) | C34—C28—C29—C30 | −1.2 (4) |
C18—N3—C20—C27 | 114.2 (2) | S2—C28—C34—C33 | 177.6 (2) |
C20—N3—C18—O8 | 177.4 (2) | C29—C28—C34—C33 | 0.1 (4) |
C19—N4—C18—N3 | 3.1 (3) | C28—C29—C30—C31 | 1.3 (4) |
C18—N4—C19—O9 | 178.2 (2) | C29—C30—C31—O10 | 179.0 (2) |
C18—N4—C19—C20 | −2.5 (3) | C29—C30—C31—C33 | −0.3 (4) |
C19—N4—C18—O8 | −176.8 (2) | O10—C31—C33—C34 | 180.0 (2) |
N2—C2—C3—C4 | −112.0 (2) | C30—C31—C33—C34 | −0.8 (4) |
N2—C2—C3—C10 | 121.7 (2) | C31—C33—C34—C28 | 0.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O8i | 0.91 (2) | 1.95 (2) | 2.851 (3) | 171 (2) |
N4—H4N···O3ii | 0.92 (2) | 1.89 (2) | 2.800 (3) | 171 (2) |
C5—H5···O2i | 0.95 | 2.36 | 3.218 (3) | 150 |
C10—H10A···O8 | 0.98 | 2.56 | 3.437 (3) | 149 |
C10—H10B···O2 | 0.98 | 2.45 | 3.055 (3) | 120 |
C12—H12···O2 | 0.95 | 2.52 | 2.905 (3) | 104 |
C13—H13···O9iii | 0.95 | 2.43 | 3.287 (3) | 150 |
C22—H22···O7ii | 0.95 | 2.42 | 3.351 (3) | 165 |
C24—H24···O8iv | 0.95 | 2.56 | 3.492 (3) | 166 |
C27—H27A···O7 | 0.98 | 2.52 | 3.126 (4) | 120 |
C29—H29···O7 | 0.95 | 2.54 | 2.916 (3) | 104 |
C30—H30···O4v | 0.95 | 2.38 | 3.159 (3) | 138 |
C34—H34···O8 | 0.95 | 2.56 | 3.291 (3) | 134 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y−1/2, −z; (v) −x, y−1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C17H16N2O5S |
Mr | 360.38 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 173 |
a, b, c (Å) | 6.2314 (6), 17.5694 (12), 15.5892 (16) |
β (°) | 99.373 (12) |
V (Å3) | 1683.9 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.38 × 0.30 × 0.19 |
Data collection | |
Diffractometer | Stoe IPDS diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13521, 6394, 4309 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.058, 0.81 |
No. of reflections | 6394 |
No. of parameters | 465 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.20 |
Absolute structure | Flack (1983), 2987 Friedel pairs |
Absolute structure parameter | 0.06 (5) |
Computer programs: EXPOSE in IPDS-I (Stoe & Cie, 2000), CELL in IPDS-I (Stoe & Cie, 2000), INTEGRATE in IPDS-I (Stoe & Cie, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O8i | 0.91 (2) | 1.95 (2) | 2.851 (3) | 171 (2) |
N4—H4N···O3ii | 0.92 (2) | 1.89 (2) | 2.800 (3) | 171 (2) |
C5—H5···O2i | 0.95 | 2.36 | 3.218 (3) | 150 |
C10—H10A···O8 | 0.98 | 2.56 | 3.437 (3) | 149 |
C10—H10B···O2 | 0.98 | 2.45 | 3.055 (3) | 120 |
C12—H12···O2 | 0.95 | 2.52 | 2.905 (3) | 104 |
C13—H13···O9iii | 0.95 | 2.43 | 3.287 (3) | 150 |
C22—H22···O7ii | 0.95 | 2.42 | 3.351 (3) | 165 |
C24—H24···O8iv | 0.95 | 2.56 | 3.492 (3) | 166 |
C27—H27A···O7 | 0.98 | 2.52 | 3.126 (4) | 120 |
C29—H29···O7 | 0.95 | 2.54 | 2.916 (3) | 104 |
C30—H30···O4v | 0.95 | 2.38 | 3.159 (3) | 138 |
C34—H34···O8 | 0.95 | 2.56 | 3.291 (3) | 134 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y−1/2, −z; (v) −x, y−1/2, −z. |
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Imidazolidine-2,4-diones have found applications as androgen receptor antagonists (Zhang et al., 2004) and possess strong anticonvulsant activity (Thenmozhiyal et al., 2004). Sulfonyl derivatives of imidazolidine-2,4-diones on the other hand, are finding utility as inhibitors of aldose reductase (Murakami et al., 1997). The potential of this class of compounds as hypoglycemic agents has already been reported from our laboratory (Kashif, Ahmad & Hameed, 2008; Ahmad et al., 2002, 2000). In continuation of our work on sulfonyl cyclic ureas (Hussain et al., 2009; Kashif, Hussain et al., 2008), the title compound was synthesized taking an imidazolidine-2,4-dione as the scaffold.
The molecular structure of the title compound is illustrated in Fig. 1, and full geometrical details are available in the archived CIF. It crystallized in the chiral monoclinic space group P21 with two enantiomeric molecues (A and B) in the asymmetric unit. It is composed of a methylimidazolidine-2,4-dione moiety substituted with a phenyl group and a 4-methoxyphenylsulfonyl group. The bond distances and angles of the two independent molecules are very similar to those observed in 1-(4-Chlorophenylsulfonyl)-5-(4-fluorophenyl)-5-methylimidazolidine-2,4-dione (Hussain et al., 2009), which also crystallized with two independent molecules per asymmetric unit but in the centrosymmetric triclinic space group P-1.
Both molecules A and B are U-shaped with slightly different conformations, as can be seen in the auto-fit view, Fig. 2 (Spek, 2009). The best fit was obtained for inverted molecule B on molecule A (25 non-H atoms) with the weighted and unit weight r.m.s. fits being 0.687 and 0.460 Å, respectively. The benzene ring mean planes are inclined to one another by 22.20 (14) ° in molecule A and 15.82 (13) ° in molecule B. This is different to the situation in the compound mentioned above where the same angles are 6.07 (8) and 8.67 (8) °, for molecules A and B, respectively (Hussain et al., 2009).
In the crystal structure of the title compound the A and B molecules are linked by N—H···O hydrogen bonds to form a dimer-like arrangement (Fig. 3 and Table 1). There are also a number of C—H···O interactions present in the crystal structure, which leads to the formation of a three-dimensional network (Fig. 4 and Table 1).