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Acta Cryst. (2009). E65, o1207-o1208    [ doi:10.1107/S1600536809016092 ]

1-(4-Methoxyphenylsulfonyl)-5-methyl-5-phenylimidazolidine-2,4-dione

A. Hussain, S. Hameed and H. Stoeckli-Evans

Abstract top

The title compound, C17H16N2O5S, crystallized in the chiral monoclinic space group P21, with two enantiomeric molecules (A and B) in the asymmetric unit. 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 crystal structure, 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 crystal structure, leading to the formation of a three-dimensinoal network.

Comment top

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).

Related literature top

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 top

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.

Refinement top

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).

Computing details top

Data collection: EXPOSE in IPDSI (Stoe & Cie, 2000); cell refinement: CELL in IPDSI (Stoe & Cie, 2000); data reduction: INTEGRATE in IPDSI (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).

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. An auto-fit view (Spek, 2009) of the two independent molecules (A black; B red) in the title compound.
[Figure 3] 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).
[Figure 4] 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).
1-(4-Methoxyphenylsulfonyl)-5-methyl-5-phenylimidazolidine-2,4-dione top
Crystal data top
C17H16N2O5SF000 = 752
Mr = 360.38Dx = 1.421 Mg m−3
Monoclinic, P21Melting point = 471–473 K
Hall symbol: P 2ybMo Kα radiation
λ = 0.71073 Å
a = 6.2314 (6) ÅCell parameters from 8000 reflections
b = 17.5694 (12) Åθ = 2.6–26.0º
c = 15.5892 (16) ŵ = 0.22 mm−1
β = 99.373 (12)ºT = 173 K
V = 1683.9 (3) Å3Rod, colourless
Z = 40.38 × 0.30 × 0.19 mm
Data collection top
Stoe IPDS
diffractometer		4309 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Monochromator: graphiteθmax = 26.1º
T = 173 Kθmin = 2.7º
φ rotation scansh = −7→7
Absorption correction: nonek = −20→21
13521 measured reflectionsl = −19→19
6394 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH 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 = 0.81Δρmax = 0.17 e Å−3
6394 reflectionsΔρmin = −0.20 e Å−3
465 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.0042 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2987 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.06 (5)
Crystal data top
C17H16N2O5SV = 1683.9 (3) Å3
Mr = 360.38Z = 4
Monoclinic, P21Mo Kα
a = 6.2314 (6) ŵ = 0.22 mm−1
b = 17.5694 (12) ÅT = 173 K
c = 15.5892 (16) Å0.38 × 0.30 × 0.19 mm
β = 99.373 (12)º
Data collection top
Stoe IPDS
diffractometer		6394 independent reflections
Absorption correction: none4309 reflections with I > 2σ(I)
13521 measured reflectionsRint = 0.033
Refinement top
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.058Δρmax = 0.17 e Å−3
S = 0.81Δρmin = −0.20 e Å−3
6394 reflectionsAbsolute structure: Flack (1983), 2987 Friedel pairs
465 parametersFlack parameter: 0.06 (5)
3 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.49288 (9)0.27479 (4)0.41621 (4)0.0322 (2)
O10.5317 (3)0.19861 (10)0.39102 (11)0.0374 (6)
O20.6619 (3)0.33014 (11)0.42511 (11)0.0414 (6)
O30.0791 (3)0.20334 (11)0.32063 (11)0.0388 (6)
O4−0.0034 (3)0.43832 (11)0.19756 (12)0.0497 (7)
O50.0979 (3)0.26824 (12)0.73090 (12)0.0622 (8)
N10.3022 (3)0.30995 (11)0.33861 (12)0.0273 (7)
N2−0.0122 (3)0.31655 (12)0.24927 (13)0.0340 (8)
C10.1190 (4)0.26883 (16)0.30444 (15)0.0299 (8)
C20.0728 (4)0.38756 (16)0.24475 (17)0.0330 (9)
C30.2862 (4)0.39125 (14)0.30845 (15)0.0285 (8)
C40.2584 (4)0.44517 (15)0.38246 (15)0.0289 (8)
C50.0795 (4)0.43753 (17)0.42345 (17)0.0409 (10)
C60.0477 (5)0.48556 (18)0.49017 (19)0.0480 (10)
C70.1927 (5)0.54235 (18)0.51559 (19)0.0519 (11)
C80.3705 (6)0.55014 (19)0.4763 (2)0.0616 (11)
C90.4043 (5)0.50230 (18)0.40945 (18)0.0483 (10)
C100.4663 (4)0.41178 (16)0.25751 (18)0.0419 (10)
C110.3765 (4)0.27369 (15)0.51029 (15)0.0303 (8)
C120.4167 (4)0.33274 (15)0.56842 (16)0.0395 (9)
C130.3248 (5)0.33334 (16)0.64261 (17)0.0447 (10)
C140.1936 (4)0.27364 (18)0.65885 (16)0.0438 (10)
C150.1345 (7)0.32823 (19)0.7938 (2)0.0826 (16)
C160.1511 (4)0.21413 (17)0.60013 (18)0.0453 (10)
C170.2418 (4)0.21460 (15)0.52550 (16)0.0360 (9)
S20.17941 (9)0.16666 (4)0.07688 (4)0.0343 (2)
O60.1557 (3)0.24522 (10)0.09316 (11)0.0443 (7)
O70.0040 (3)0.11541 (11)0.07948 (12)0.0434 (6)
O80.5996 (3)0.24274 (10)0.16846 (11)0.0382 (6)
O90.7248 (3)0.00425 (10)0.27716 (11)0.0390 (6)
O100.5175 (3)0.11964 (11)−0.24698 (12)0.0523 (7)
N30.3788 (3)0.13476 (12)0.15370 (13)0.0285 (7)
N40.7059 (3)0.12965 (12)0.23550 (12)0.0295 (7)
C180.5652 (4)0.17648 (16)0.18420 (15)0.0290 (8)
C190.6295 (4)0.05719 (16)0.23806 (15)0.0300 (8)
C200.4033 (4)0.05427 (15)0.18445 (15)0.0286 (8)
C210.4028 (4)−0.00248 (14)0.10977 (15)0.0284 (8)
C220.5752 (4)−0.00181 (16)0.06382 (15)0.0354 (9)
C230.5797 (4)−0.05236 (18)−0.00387 (17)0.0442 (10)
C240.4127 (5)−0.10347 (16)−0.02589 (17)0.0466 (10)
C250.2398 (5)−0.10367 (18)0.01867 (19)0.0488 (11)
C260.2350 (4)−0.05315 (16)0.08642 (17)0.0390 (9)
C270.2452 (5)0.03531 (17)0.24687 (19)0.0424 (10)
C280.2780 (4)0.15486 (15)−0.02036 (16)0.0318 (8)
C290.1934 (4)0.09875 (15)−0.07862 (16)0.0338 (8)
C300.2755 (4)0.08912 (15)−0.15410 (16)0.0366 (9)
C310.4463 (4)0.13473 (15)−0.17102 (16)0.0375 (9)
C320.6969 (5)0.1640 (2)−0.26728 (19)0.0633 (13)
C330.5329 (4)0.18981 (17)−0.11248 (17)0.0487 (10)
C340.4462 (4)0.19955 (17)−0.03783 (17)0.0453 (10)
H2N−0.143 (3)0.2979 (16)0.2234 (17)0.057 (9)*
H5−0.023600.398500.405400.0490*
H6−0.075200.479000.518400.0580*
H70.169600.576300.560600.0620*
H80.473300.589100.495000.0740*
H90.528600.508900.382100.0580*
H10A0.472200.373700.212000.0630*
H10B0.606000.412900.296900.0630*
H10C0.436900.462000.230700.0630*
H120.508800.373400.557200.0470*
H130.351200.374500.682400.0540*
H15A0.290500.332200.816100.1240*
H15B0.082300.376400.766300.1240*
H15C0.055800.317100.841800.1240*
H160.059900.173300.611400.0540*
H170.211900.174400.484500.0430*
H4N0.835 (3)0.1490 (15)0.2635 (16)0.053 (9)*
H220.690700.033500.078900.0420*
H230.69830−0.05180−0.035200.0530*
H240.41700−0.13860−0.071900.0560*
H250.12350−0.138500.003000.0590*
H260.11500−0.053400.117000.0470*
H27A0.096000.035900.215100.0640*
H27B0.259700.073200.293600.0640*
H27C0.27880−0.015300.271900.0640*
H290.078800.06710−0.066200.0410*
H300.216000.05140−0.194800.0440*
H32A0.824000.15630−0.222100.0950*
H32B0.657200.21800−0.270000.0950*
H32C0.731700.14780−0.323600.0950*
H330.650700.22050−0.123700.0580*
H340.503500.237900.002500.0540*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0318 (3)0.0308 (4)0.0350 (3)0.0037 (3)0.0081 (3)0.0046 (3)
O10.0456 (10)0.0279 (11)0.0406 (10)0.0154 (8)0.0127 (8)0.0030 (8)
O20.0309 (9)0.0458 (13)0.0475 (11)−0.0090 (9)0.0062 (8)0.0103 (10)
O30.0469 (10)0.0229 (12)0.0444 (11)−0.0020 (8)0.0006 (8)−0.0035 (9)
O40.0650 (12)0.0332 (12)0.0448 (11)0.0118 (10)−0.0093 (9)0.0037 (10)
O50.0954 (15)0.0495 (14)0.0531 (12)0.0007 (12)0.0464 (11)−0.0022 (11)
N10.0297 (10)0.0221 (13)0.0300 (11)0.0007 (8)0.0046 (9)−0.0009 (9)
N20.0392 (13)0.0240 (14)0.0355 (12)0.0028 (10)−0.0037 (10)−0.0047 (10)
C10.0356 (13)0.0231 (16)0.0305 (13)0.0035 (13)0.0038 (10)−0.0040 (12)
C20.0422 (15)0.0260 (17)0.0308 (15)0.0074 (12)0.0060 (12)−0.0041 (12)
C30.0352 (13)0.0192 (15)0.0315 (14)0.0022 (10)0.0068 (11)0.0020 (11)
C40.0350 (13)0.0224 (15)0.0289 (13)0.0001 (11)0.0043 (11)0.0009 (11)
C50.0381 (15)0.0392 (19)0.0462 (17)−0.0060 (13)0.0092 (13)−0.0137 (14)
C60.0500 (17)0.055 (2)0.0410 (16)0.0091 (15)0.0136 (13)−0.0104 (14)
C70.083 (2)0.035 (2)0.0374 (16)0.0077 (16)0.0091 (16)−0.0062 (14)
C80.091 (2)0.046 (2)0.0474 (19)−0.0311 (18)0.0097 (18)−0.0166 (16)
C90.0581 (17)0.041 (2)0.0479 (17)−0.0172 (15)0.0152 (14)−0.0016 (15)
C100.0473 (16)0.0388 (19)0.0435 (16)0.0055 (13)0.0187 (13)0.0089 (13)
C110.0329 (12)0.0241 (15)0.0346 (13)−0.0004 (12)0.0078 (10)0.0022 (12)
C120.0529 (16)0.0253 (17)0.0408 (15)−0.0063 (12)0.0091 (13)0.0031 (13)
C130.0721 (19)0.0257 (17)0.0390 (15)−0.0021 (14)0.0175 (14)−0.0040 (12)
C140.0571 (17)0.0390 (18)0.0404 (15)0.0067 (15)0.0234 (13)0.0032 (14)
C150.154 (4)0.048 (2)0.060 (2)0.012 (2)0.060 (2)−0.0070 (18)
C160.0553 (17)0.0359 (19)0.0496 (17)−0.0069 (13)0.0235 (13)−0.0008 (14)
C170.0407 (14)0.0306 (17)0.0384 (14)−0.0018 (12)0.0117 (11)−0.0037 (12)
S20.0317 (3)0.0336 (4)0.0382 (4)0.0030 (3)0.0073 (3)−0.0010 (3)
O60.0518 (11)0.0318 (13)0.0487 (11)0.0145 (9)0.0062 (9)−0.0040 (9)
O70.0269 (9)0.0545 (13)0.0501 (11)−0.0038 (9)0.0101 (8)0.0012 (10)
O80.0482 (10)0.0232 (12)0.0417 (11)−0.0054 (8)0.0026 (8)−0.0007 (8)
O90.0500 (10)0.0287 (12)0.0367 (10)0.0005 (9)0.0024 (8)0.0032 (9)
O100.0612 (12)0.0570 (15)0.0427 (11)−0.0077 (10)0.0202 (9)−0.0060 (10)
N30.0325 (10)0.0199 (13)0.0335 (11)−0.0013 (8)0.0064 (9)−0.0012 (9)
N40.0337 (12)0.0226 (13)0.0320 (12)−0.0019 (10)0.0050 (9)−0.0015 (9)
C180.0330 (13)0.0269 (17)0.0284 (13)0.0023 (12)0.0085 (10)−0.0048 (12)
C190.0430 (15)0.0258 (16)0.0231 (13)−0.0004 (12)0.0109 (11)−0.0014 (11)
C200.0325 (13)0.0228 (15)0.0325 (14)−0.0023 (10)0.0114 (11)−0.0041 (11)
C210.0323 (13)0.0204 (15)0.0324 (14)−0.0014 (11)0.0050 (11)−0.0017 (11)
C220.0345 (13)0.0394 (18)0.0334 (14)−0.0009 (12)0.0090 (11)−0.0068 (12)
C230.0547 (17)0.0437 (19)0.0353 (15)0.0077 (15)0.0105 (13)−0.0057 (14)
C240.077 (2)0.0272 (18)0.0341 (15)0.0070 (15)0.0050 (15)−0.0063 (13)
C250.0674 (19)0.0307 (19)0.0450 (17)−0.0152 (14)−0.0007 (15)−0.0053 (14)
C260.0448 (15)0.0308 (17)0.0421 (16)−0.0109 (13)0.0088 (12)−0.0017 (13)
C270.0479 (16)0.0352 (19)0.0494 (18)−0.0030 (13)0.0242 (14)−0.0004 (13)
C280.0326 (12)0.0291 (16)0.0331 (13)0.0000 (11)0.0037 (10)0.0007 (11)
C290.0328 (13)0.0308 (16)0.0371 (14)−0.0056 (11)0.0033 (11)0.0006 (12)
C300.0426 (15)0.0297 (17)0.0360 (15)−0.0056 (12)0.0023 (12)−0.0042 (12)
C310.0429 (14)0.0403 (18)0.0303 (14)−0.0028 (13)0.0088 (11)0.0005 (12)
C320.0559 (18)0.088 (3)0.0501 (17)−0.0130 (19)0.0212 (14)0.0026 (18)
C330.0520 (16)0.055 (2)0.0409 (16)−0.0264 (14)0.0131 (13)−0.0059 (14)
C340.0553 (17)0.0441 (19)0.0362 (15)−0.0192 (14)0.0069 (13)−0.0085 (13)
Geometric parameters (Å, °) top
S1—O11.4266 (19)C7—H70.9500
S1—O21.424 (2)C8—H80.9500
S1—N11.670 (2)C9—H90.9500
S1—C111.739 (2)C10—H10B0.9800
S2—N31.676 (2)C10—H10A0.9800
S2—O61.4155 (19)C10—H10C0.9800
S2—O71.422 (2)C12—H120.9500
S2—C281.738 (3)C13—H130.9500
O3—C11.212 (3)C15—H15B0.9800
O4—C21.203 (3)C15—H15A0.9800
O5—C141.358 (3)C15—H15C0.9800
O5—C151.432 (4)C16—H160.9500
O8—C181.216 (3)C17—H170.9500
O9—C191.213 (3)C19—C201.518 (3)
O10—C311.357 (3)C20—C271.530 (4)
O10—C321.440 (4)C20—C211.532 (3)
N1—C11.382 (3)C21—C221.385 (3)
N1—C31.502 (3)C21—C261.376 (4)
N2—C11.372 (3)C22—C231.383 (4)
N2—C21.362 (3)C23—C241.375 (4)
N2—H2N0.91 (2)C24—C251.374 (4)
N3—C201.493 (3)C25—C261.384 (4)
N3—C181.390 (3)C28—C341.372 (4)
N4—C181.363 (3)C28—C291.385 (4)
N4—C191.362 (3)C29—C301.368 (4)
N4—H4N0.92 (2)C30—C311.391 (4)
C2—C31.526 (4)C31—C331.378 (4)
C3—C41.524 (3)C33—C341.371 (4)
C3—C101.520 (4)C22—H220.9500
C4—C91.374 (4)C23—H230.9500
C4—C51.379 (4)C24—H240.9500
C5—C61.379 (4)C25—H250.9500
C6—C71.361 (4)C26—H260.9500
C7—C81.357 (5)C27—H27A0.9800
C8—C91.381 (4)C27—H27B0.9800
C11—C171.380 (4)C27—H27C0.9800
C11—C121.373 (4)C29—H290.9500
C12—C131.372 (4)C30—H300.9500
C13—C141.378 (4)C32—H32A0.9800
C14—C161.387 (4)C32—H32B0.9800
C16—C171.374 (4)C32—H32C0.9800
C5—H50.9500C33—H330.9500
C6—H60.9500C34—H340.9500
O1—S1—O2120.78 (12)C13—C12—H12120.00
O1—S1—N1106.27 (10)C14—C13—H13120.00
O1—S1—C11109.54 (12)C12—C13—H13120.00
O2—S1—N1104.23 (11)O5—C15—H15B109.00
O2—S1—C11109.21 (12)O5—C15—H15A109.00
N1—S1—C11105.65 (11)H15A—C15—H15B109.00
O7—S2—N3104.59 (11)H15A—C15—H15C110.00
O7—S2—C28109.38 (12)O5—C15—H15C109.00
N3—S2—C28104.90 (11)H15B—C15—H15C110.00
O6—S2—C28109.55 (12)C14—C16—H16120.00
O6—S2—O7120.61 (12)C17—C16—H16120.00
O6—S2—N3106.56 (11)C16—C17—H17120.00
C14—O5—C15118.2 (2)C11—C17—H17120.00
C31—O10—C32117.5 (2)N3—C18—N4107.7 (2)
S1—N1—C1122.10 (17)O8—C18—N3126.9 (2)
S1—N1—C3125.57 (16)O8—C18—N4125.4 (2)
C1—N1—C3111.58 (19)O9—C19—C20125.8 (2)
C1—N2—C2113.3 (2)O9—C19—N4125.9 (2)
C2—N2—H2N129.4 (18)N4—C19—C20108.3 (2)
C1—N2—H2N117.2 (18)N3—C20—C21112.64 (19)
S2—N3—C18123.31 (18)N3—C20—C19100.5 (2)
S2—N3—C20124.85 (16)C19—C20—C27107.1 (2)
C18—N3—C20110.71 (19)C21—C20—C27114.8 (2)
C18—N4—C19112.8 (2)N3—C20—C27111.6 (2)
C18—N4—H4N119.1 (16)C19—C20—C21109.1 (2)
C19—N4—H4N128.1 (16)C22—C21—C26119.3 (2)
N1—C1—N2107.0 (2)C20—C21—C22118.8 (2)
O3—C1—N1126.9 (2)C20—C21—C26122.0 (2)
O3—C1—N2126.1 (2)C21—C22—C23120.2 (2)
O4—C2—C3125.6 (2)C22—C23—C24120.1 (2)
O4—C2—N2126.3 (2)C23—C24—C25120.0 (3)
N2—C2—C3108.1 (2)C24—C25—C26120.0 (3)
N1—C3—C10111.9 (2)C21—C26—C25120.5 (2)
N1—C3—C4111.35 (19)C29—C28—C34119.9 (2)
N1—C3—C299.77 (19)S2—C28—C29120.4 (2)
C2—C3—C4108.9 (2)S2—C28—C34119.7 (2)
C2—C3—C10108.0 (2)C28—C29—C30119.8 (2)
C4—C3—C10115.6 (2)C29—C30—C31119.8 (2)
C5—C4—C9118.3 (2)O10—C31—C33124.5 (2)
C3—C4—C9122.3 (2)O10—C31—C30115.0 (2)
C3—C4—C5119.4 (2)C30—C31—C33120.5 (2)
C4—C5—C6121.1 (3)C31—C33—C34118.9 (2)
C5—C6—C7119.9 (3)C28—C34—C33121.1 (3)
C6—C7—C8119.6 (3)C21—C22—H22120.00
C7—C8—C9121.0 (3)C23—C22—H22120.00
C4—C9—C8120.1 (3)C22—C23—H23120.00
S1—C11—C17120.15 (19)C24—C23—H23120.00
S1—C11—C12119.5 (2)C23—C24—H24120.00
C12—C11—C17120.4 (2)C25—C24—H24120.00
C11—C12—C13120.4 (2)C24—C25—H25120.00
C12—C13—C14119.4 (3)C26—C25—H25120.00
O5—C14—C16115.5 (3)C21—C26—H26120.00
C13—C14—C16120.5 (2)C25—C26—H26120.00
O5—C14—C13124.0 (3)C20—C27—H27A109.00
C14—C16—C17119.6 (3)C20—C27—H27B110.00
C11—C17—C16119.7 (2)C20—C27—H27C109.00
C4—C5—H5119.00H27A—C27—H27B109.00
C6—C5—H5119.00H27A—C27—H27C110.00
C5—C6—H6120.00H27B—C27—H27C109.00
C7—C6—H6120.00C28—C29—H29120.00
C6—C7—H7120.00C30—C29—H29120.00
C8—C7—H7120.00C29—C30—H30120.00
C7—C8—H8120.00C31—C30—H30120.00
C9—C8—H8119.00O10—C32—H32A109.00
C4—C9—H9120.00O10—C32—H32B110.00
C8—C9—H9120.00O10—C32—H32C109.00
H10A—C10—H10B109.00H32A—C32—H32B109.00
H10A—C10—H10C109.00H32A—C32—H32C109.00
C3—C10—H10C109.00H32B—C32—H32C109.00
C3—C10—H10B109.00C31—C33—H33121.00
C3—C10—H10A110.00C34—C33—H33121.00
H10B—C10—H10C110.00C28—C34—H34119.00
C11—C12—H12120.00C33—C34—H34119.00
O1—S1—N1—C144.6 (2)N2—C2—C3—N14.8 (2)
O1—S1—N1—C3−146.18 (18)O4—C2—C3—N1−173.7 (2)
O2—S1—N1—C1173.23 (18)O4—C2—C3—C469.6 (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—C397.5 (2)N1—C3—C4—C9120.3 (3)
O1—S1—C11—C12149.2 (2)C2—C3—C4—C548.5 (3)
O1—S1—C11—C17−31.9 (2)N1—C3—C4—C5−60.6 (3)
O2—S1—C11—C1214.9 (2)C10—C3—C4—C5170.3 (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—C1782.2 (2)C3—C4—C5—C6−179.5 (2)
O6—S2—N3—C18−38.6 (2)C3—C4—C9—C8179.4 (3)
O6—S2—N3—C20154.74 (18)C5—C4—C9—C80.3 (4)
O7—S2—N3—C18−167.37 (19)C4—C5—C6—C71.0 (4)
O7—S2—N3—C2026.0 (2)C5—C6—C7—C8−1.5 (5)
C28—S2—N3—C1877.5 (2)C6—C7—C8—C91.5 (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—C13179.4 (2)
O6—S2—C28—C3444.6 (3)C17—C11—C12—C130.5 (4)
O7—S2—C28—C29−3.6 (3)S1—C11—C17—C16179.8 (2)
O7—S2—C28—C34178.9 (2)C12—C11—C17—C16−1.4 (4)
N3—S2—C28—C29108.1 (2)C11—C12—C13—C140.8 (4)
N3—S2—C28—C34−69.4 (2)C12—C13—C14—O5178.9 (3)
C15—O5—C14—C130.2 (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—C170.4 (4)
C32—O10—C31—C330.5 (4)C14—C16—C17—C110.9 (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—N2174.13 (15)O9—C19—C20—C2763.6 (3)
C3—N1—C1—O3−175.6 (2)N4—C19—C20—N30.9 (2)
C3—N1—C1—N23.6 (3)N4—C19—C20—C21119.4 (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—C2267.3 (3)
S1—N1—C3—C1070.7 (2)N3—C20—C21—C26−111.8 (3)
C1—N1—C3—C4109.9 (2)C19—C20—C21—C22−43.4 (3)
C1—N1—C3—C10−119.1 (2)C19—C20—C21—C26137.6 (2)
C1—N2—C2—O4175.3 (3)C27—C20—C21—C22−163.5 (2)
C2—N2—C1—O3179.0 (2)C27—C20—C21—C2617.4 (3)
C2—N2—C1—N1−0.2 (3)C20—C21—C22—C23179.9 (2)
C1—N2—C2—C3−3.2 (3)C26—C21—C22—C23−1.0 (4)
S2—N3—C18—O89.1 (4)C20—C21—C26—C25−180.0 (3)
S2—N3—C18—N4−170.73 (16)C22—C21—C26—C251.0 (4)
C20—N3—C18—N4−2.4 (3)C21—C22—C23—C240.1 (4)
S2—N3—C20—C19169.04 (16)C22—C23—C24—C250.8 (4)
S2—N3—C20—C2153.1 (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—C190.9 (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—C27114.2 (2)S2—C28—C34—C33177.6 (2)
C20—N3—C18—O8177.4 (2)C29—C28—C34—C330.1 (4)
C19—N4—C18—N33.1 (3)C28—C29—C30—C311.3 (4)
C18—N4—C19—O9178.2 (2)C29—C30—C31—O10179.0 (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—C34180.0 (2)
N2—C2—C3—C4−112.0 (2)C30—C31—C33—C34−0.8 (4)
N2—C2—C3—C10121.7 (2)C31—C33—C34—C280.9 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O8i0.91 (2)1.95 (2)2.851 (3)171 (2)
N4—H4N···O3ii0.92 (2)1.89 (2)2.800 (3)171 (2)
C5—H5···O2i0.952.363.218 (3)150
C10—H10A···O80.982.563.437 (3)149
C10—H10B···O20.982.453.055 (3)120
C12—H12···O20.952.522.905 (3)104
C13—H13···O9iii0.952.433.287 (3)150
C22—H22···O7ii0.952.423.351 (3)165
C24—H24···O8iv0.952.563.492 (3)166
C27—H27A···O70.982.523.126 (4)120
C29—H29···O70.952.542.916 (3)104
C30—H30···O4v0.952.383.159 (3)138
C34—H34···O80.952.563.291 (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.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O8i0.91 (2)1.95 (2)2.851 (3)171 (2)
N4—H4N···O3ii0.92 (2)1.89 (2)2.800 (3)171 (2)
C5—H5···O2i0.952.363.218 (3)150
C10—H10A···O80.982.563.437 (3)149
C10—H10B···O20.982.453.055 (3)120
C12—H12···O20.952.522.905 (3)104
C13—H13···O9iii0.952.433.287 (3)150
C22—H22···O7ii0.952.423.351 (3)165
C24—H24···O8iv0.952.563.492 (3)166
C27—H27A···O70.982.523.126 (4)120
C29—H29···O70.952.542.916 (3)104
C30—H30···O4v0.952.383.159 (3)138
C34—H34···O80.952.563.291 (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.
Acknowledgements top

none

references
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