PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o858–o859.
Published online 2009 March 25. doi:  10.1107/S160053680901037X
PMCID: PMC2968985

1-(4-Chloro­phenyl­sulfon­yl)-5-(4-fluoro­phen­yl)-5-methyl­imidazolidine-2,4-dione

Abstract

The title compound, C16H12ClFN2O4S, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The two mol­ecules are U-shaped with similar geometries and conformations. The mean planes through the benzene rings are inclined to one another by 6.07 (8)° in mol­ecule A and 8.67 (8)° in mol­ecule B. They are separated with a centroid–centroid distance of 3.9096 (10) Å in mol­ecule A and 3.9118 (10) Å in mol­ecule B. Mol­ecules A and B lie adjacent to one another, with a centroid–centroid distance of 3.7592 (10) Å between the fluoro­phenyl ring of mol­ecule A and the chloro­phenyl­sulfonyl ring of mol­ecule B and with a dihedral angle of 5.75 (8)° between the ring planes. In the crystal structure, A and B mol­ecules are linked by N—H(...)O hydrogen bonds, forming centrosymmetric dimers. These dimers stack along the [110] direction and are linked by C—H(...)O and C—H(...)F inter­actions. There are also some short halide(...)halide contacts [Cl(...)F = 3.0499 (14) and 3.1224 (13) Å, and F(...)F = 3.0612 (17) Å].

Related literature

For the biological activity of imidazolidine-2,4-diones, see: Muccioli et al. (2006 [triangle]); Flosi et al. (2006 [triangle]). For the biological activity of sulfonyl derivatives of imidazolidine-2,4-diones, see: Kato, Nakayama, Mizota et al. (1991 [triangle]); Kato, Nakayama, Ohta et al. (1991 [triangle]); Ahmad et al. (2000 [triangle], 2002 [triangle]); Kashif, Ahmad & Hameed (2008 [triangle]). For the crystal structure of 5-(4-fluoro­phen­yl)-5-methyl­imidazolidine-2,4-dione, see: Kashif, Hussain et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o858-scheme1.jpg

Experimental

Crystal data

  • C16H12ClFN2O4S
  • M r = 382.79
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o858-efi1.jpg
  • a = 9.6959 (7) Å
  • b = 10.0066 (7) Å
  • c = 16.6269 (13) Å
  • α = 92.098 (6)°
  • β = 93.630 (6)°
  • γ = 103.056 (6)°
  • V = 1566.2 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.41 mm−1
  • T = 173 K
  • 0.45 × 0.40 × 0.24 mm

Data collection

  • Stoe IPDS-2 diffractometer
  • Absorption correction: none
  • 30542 measured reflections
  • 8438 independent reflections
  • 5836 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.095
  • S = 0.89
  • 8438 reflections
  • 462 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.64 e Å−3

Data collection: X-AREA (Stoe & Cie, 2006 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2006 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901037X/nc2138sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901037X/nc2138Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Immidazolidine-2,4-diones are a valuable class of cyclic urea derivatives exhibiting a broad spectrum of activities ranging from fatty acid amide hydrolase inhibitors (Muccioli et al., 2006) to HIV protease inhibitors (Flosi et al., 2006). Their sulfonyl derivatives not only possess strong inhibitory activity against aldose reductase (Kato, Nakayama, Mizota et al., 1991) but also address diabetic complications such as neuropathy and cataract formation (Kato, Nakayama, Ohta, et al., 1991). Hypoglycemic and aldose reductase inhibitory assay of this novel class of compounds has been reported from this laboratory (Ahmad et al., 2000; Ahmad et al., 2002; Kashif, Ahmad & Hameed, 2008). The crystal structure of 5-(4-Fluorophenyl)-5-methylimidazolidine-2,4-dione (Kashif, Hussain et al., 2008) has been reported previously. The title compound was synthesized by sulfonylation of 5-(4-Fluorophenyl)-5-methylimidazolidine-2,4-dione, to access its hypoglycemic activity.

The title compound crystallizes with two independent molecues (A and B) in the asymmetric unit. It is composed of a methylimidazolidine-2,4-dione moiety substituted with a p-fluorophenyl group and a p-chlorophenylsulfonyl group. Both molecules are U-shaped with a similar geometry and conformation, as can be seen from the Auto-Fit diagram (Fig. 2: Weighted and Unit Weight RMS-Fit = 0.075, 0.069 Å, respectively, for 25 non-H atoms; Spek, 2009). The phenyl ring mean planes are inclined to one another by 6.07 (8)° in molecule A and 8.67 (8)° in molecule B. They are separated with a centroid-to-centroid distance of 3.9096 (10) Å in molecule A, and 3.9118 (10) Å in molecule B. Molecules A and B lie adjacent to one another with a centroid-to-centroid distance of 3.7591 (10) Å between the fluorophenyl ring of molecule A and the chlorophenylsulfonyl ring of molecule B (Fig. 1).

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). These dimers stack along the direction [110] and are linked by C—H···O interactions. The stacks are also linked by C—H···F interactions, and there are some short halide···halide contacts: 3.0499 (14) Å for Cl1···F2i and 3.1224 (13) Å, for Cl2···F1i [symmetry operation (i) -x+1, -y, -z+1]) and 3.0612 (17) Å for F1···F2ii [symmetry operation (ii) -x+1, -y+1, -z+1].

Experimental

5-(4-Fluorophenyl)-5-methylimidazolidine-2,4-dione (4.8 mmol) in CH2Cl2 (20 ml) as stirred with triethyl amine (4.8 mmol) and catalytic amounts of DMAP. 4-Chlorobenzene sulfonyl chloride (5.8 mmol) in CH2Cl2 (10 ml) was added drop wise and the reaction mixture was stirred at rt until complete (controled by TLC). The reaction mixture was diluted with 1 N HCl (20 ml) 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 the title compound as colourless plate-like crystals, suitable for X-ray analysis.

Refinement

The NH H-atoms were located in difference Fourier maps and freely refined: N—H = 0.84 (2) - 0.875 (19) Å. The other H-atoms were included in calculated positions and treated as riding atoms: C—H = 0.995 - 0.98 Å, with Uiso(H) = k × Ueq(parent C-atom), where k = 1.2 (aromatic H) and 1.5(methyl H).

Figures

Fig. 1.
A view of molecular structure of the two independent molecules (A-left & B-right) of the title compound. The displacement ellipsoids are drawn at the 50% probability 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 b axis showing the crystal packing in the title compound: Molecule A is black; Molecule B is red [The N—H···O and C—H···O hydrogen bonds are shown as dashed lines; H-atoms ...

Crystal data

C16H12ClFN2O4SZ = 4
Mr = 382.79F(000) = 784
Triclinic, P1Dx = 1.623 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6959 (7) ÅCell parameters from 20500 reflections
b = 10.0066 (7) Åθ = 2.1–29.5°
c = 16.6269 (13) ŵ = 0.41 mm1
α = 92.098 (6)°T = 173 K
β = 93.630 (6)°Plate, colourless
γ = 103.056 (6)°0.45 × 0.40 × 0.24 mm
V = 1566.2 (2) Å3

Data collection

Stoe IPDS-2 diffractometer5836 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
graphiteθmax = 29.3°, θmin = 2.1°
[var phi] and ω scansh = −13→12
30542 measured reflectionsk = −13→13
8438 independent reflectionsl = −22→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095w = 1/[σ2(Fo2) + (0.0594P)2] where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max = 0.001
8438 reflectionsΔρmax = 0.49 e Å3
462 parametersΔρmin = −0.64 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0070 (7)

Special details

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)

xyzUiso*/Ueq
Cl10.91764 (7)−0.33306 (8)0.44481 (3)0.0678 (2)
S11.07493 (4)0.03707 (4)0.15675 (2)0.0216 (1)
F10.74943 (12)0.11810 (12)0.46455 (6)0.0435 (4)
O10.88878 (13)−0.18444 (11)0.04068 (7)0.0292 (3)
O20.57120 (12)0.08199 (11)0.07970 (6)0.0266 (3)
O31.12161 (12)0.17630 (11)0.18656 (8)0.0317 (3)
O41.15471 (12)−0.02016 (12)0.10155 (7)0.0306 (3)
N10.91377 (13)0.02536 (12)0.11173 (7)0.0188 (3)
N20.70525 (14)−0.07265 (13)0.04699 (7)0.0217 (4)
C11.04515 (16)−0.06802 (16)0.23943 (9)0.0239 (4)
C21.06304 (19)−0.00804 (19)0.31679 (10)0.0324 (5)
C31.0280 (2)−0.0905 (2)0.38108 (10)0.0412 (6)
C40.9731 (2)−0.2300 (2)0.36571 (11)0.0399 (6)
C50.95939 (19)−0.29070 (19)0.28916 (11)0.0350 (5)
C60.99744 (17)−0.20954 (16)0.22461 (10)0.0271 (5)
C70.84130 (17)−0.08949 (14)0.06303 (8)0.0211 (4)
C80.68087 (16)0.04368 (14)0.08337 (8)0.0192 (4)
C90.81941 (15)0.11962 (13)0.13079 (8)0.0175 (4)
C100.86819 (16)0.25816 (14)0.09386 (9)0.0227 (4)
C110.79666 (15)0.12483 (14)0.22069 (8)0.0180 (4)
C120.84186 (16)0.24448 (15)0.26969 (9)0.0230 (4)
C130.82563 (18)0.24327 (17)0.35230 (9)0.0287 (5)
C140.76299 (18)0.12121 (18)0.38395 (9)0.0282 (5)
C150.71357 (17)0.00078 (16)0.33735 (9)0.0264 (4)
C160.73163 (16)0.00364 (15)0.25529 (8)0.0221 (4)
Cl20.40511 (6)0.12790 (6)0.43991 (3)0.0533 (2)
S20.58277 (4)0.54282 (4)0.17383 (2)0.0238 (1)
F20.23250 (13)0.58675 (13)0.47233 (6)0.0462 (4)
O50.41852 (14)0.33765 (12)0.04019 (7)0.0323 (4)
O60.08075 (12)0.57818 (11)0.08571 (6)0.0268 (3)
O70.62142 (12)0.67806 (11)0.21087 (8)0.0329 (4)
O80.67356 (13)0.49688 (12)0.12089 (8)0.0349 (4)
N30.42774 (14)0.53320 (12)0.12274 (7)0.0207 (4)
N40.22860 (15)0.43999 (13)0.04734 (7)0.0245 (4)
C170.54287 (17)0.42502 (15)0.25006 (9)0.0246 (4)
C180.55335 (19)0.47308 (18)0.32980 (10)0.0314 (5)
C190.5129 (2)0.3808 (2)0.38883 (10)0.0366 (6)
C200.46166 (19)0.24306 (19)0.36642 (10)0.0340 (5)
C210.45376 (18)0.19449 (17)0.28735 (10)0.0313 (5)
C220.49622 (17)0.28577 (15)0.22782 (9)0.0258 (4)
C230.36440 (17)0.42562 (15)0.06618 (8)0.0234 (4)
C240.19359 (16)0.54614 (14)0.08942 (8)0.0203 (4)
C250.32640 (15)0.62082 (13)0.14231 (8)0.0181 (4)
C260.37432 (17)0.76406 (14)0.11053 (9)0.0235 (4)
C270.29616 (15)0.61719 (14)0.23119 (8)0.0188 (4)
C280.34294 (17)0.73075 (15)0.28478 (9)0.0250 (4)
C290.32074 (18)0.72166 (17)0.36611 (10)0.0312 (5)
C300.25095 (18)0.59752 (18)0.39255 (9)0.0300 (5)
C310.19982 (18)0.48331 (17)0.34161 (9)0.0280 (5)
C320.22340 (16)0.49359 (15)0.26027 (9)0.0226 (4)
H21.098800.088200.325800.0390*
H2N0.646 (2)−0.124 (2)0.0142 (12)0.037 (5)*
H31.04140−0.051900.434800.0490*
H50.92420−0.387100.280600.0420*
H60.99110−0.249600.171400.0330*
H10A0.883200.243600.036800.0340*
H10B0.957300.308600.122500.0340*
H10C0.795500.311400.098600.0340*
H120.884300.327900.246500.0280*
H130.857000.324700.385900.0340*
H150.66860−0.081500.360800.0320*
H160.69920−0.078200.222100.0260*
H4N0.170 (2)0.3855 (19)0.0117 (11)0.031 (5)*
H180.587800.568200.343900.0380*
H190.520300.411700.444000.0440*
H210.419500.099200.273600.0370*
H220.493500.253800.173100.0310*
H26A0.389900.755900.053100.0350*
H26B0.462900.812500.140500.0350*
H26C0.300800.815600.117700.0350*
H280.390800.815700.265400.0300*
H290.352900.799300.402700.0370*
H310.149800.399700.361500.0340*
H320.189700.415700.224000.0270*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0535 (3)0.1057 (5)0.0463 (3)0.0147 (3)0.0103 (2)0.0444 (3)
S10.0190 (2)0.0171 (2)0.0295 (2)0.0054 (1)0.0028 (1)0.0019 (1)
F10.0520 (7)0.0584 (7)0.0186 (4)0.0092 (6)0.0052 (4)−0.0020 (4)
O10.0364 (7)0.0210 (5)0.0314 (6)0.0107 (5)0.0030 (5)−0.0080 (4)
O20.0221 (6)0.0302 (6)0.0276 (5)0.0082 (5)−0.0011 (4)−0.0042 (4)
O30.0229 (6)0.0182 (5)0.0510 (7)0.0013 (4)−0.0054 (5)−0.0014 (5)
O40.0285 (6)0.0317 (6)0.0378 (6)0.0155 (5)0.0141 (5)0.0092 (5)
N10.0203 (6)0.0147 (5)0.0224 (6)0.0064 (5)0.0025 (5)−0.0006 (4)
N20.0227 (7)0.0201 (6)0.0204 (6)0.0017 (5)0.0021 (5)−0.0065 (5)
C10.0226 (8)0.0254 (8)0.0254 (7)0.0096 (6)0.0004 (6)0.0015 (6)
C20.0339 (9)0.0370 (9)0.0283 (8)0.0156 (7)−0.0056 (7)−0.0050 (7)
C30.0420 (11)0.0633 (13)0.0245 (8)0.0260 (10)0.0002 (7)0.0011 (8)
C40.0297 (9)0.0606 (13)0.0338 (9)0.0160 (9)0.0046 (7)0.0213 (8)
C50.0292 (9)0.0355 (9)0.0400 (9)0.0057 (7)−0.0013 (7)0.0139 (7)
C60.0277 (8)0.0244 (8)0.0290 (8)0.0057 (6)−0.0006 (6)0.0042 (6)
C70.0283 (8)0.0156 (6)0.0192 (6)0.0045 (6)0.0047 (5)−0.0015 (5)
C80.0220 (7)0.0182 (6)0.0164 (6)0.0021 (5)0.0027 (5)0.0005 (5)
C90.0191 (7)0.0127 (6)0.0214 (6)0.0048 (5)0.0029 (5)−0.0004 (5)
C100.0249 (8)0.0166 (7)0.0279 (7)0.0057 (6)0.0049 (6)0.0057 (5)
C110.0185 (7)0.0152 (6)0.0200 (6)0.0038 (5)0.0013 (5)−0.0012 (5)
C120.0232 (8)0.0177 (7)0.0263 (7)0.0016 (6)0.0030 (6)−0.0031 (5)
C130.0297 (9)0.0279 (8)0.0269 (7)0.0054 (7)0.0000 (6)−0.0102 (6)
C140.0285 (8)0.0390 (9)0.0179 (7)0.0097 (7)0.0028 (6)−0.0012 (6)
C150.0287 (8)0.0264 (8)0.0242 (7)0.0054 (6)0.0041 (6)0.0048 (6)
C160.0249 (8)0.0180 (7)0.0223 (7)0.0029 (6)0.0018 (6)0.0005 (5)
Cl20.0499 (3)0.0667 (4)0.0426 (3)0.0081 (3)0.0044 (2)0.0272 (2)
S20.0205 (2)0.0163 (2)0.0358 (2)0.0056 (1)0.0049 (2)0.0018 (1)
F20.0560 (7)0.0628 (7)0.0196 (5)0.0125 (6)0.0054 (5)0.0011 (4)
O50.0425 (7)0.0245 (6)0.0328 (6)0.0144 (5)0.0061 (5)−0.0079 (4)
O60.0237 (6)0.0278 (6)0.0280 (5)0.0056 (5)0.0004 (4)−0.0041 (4)
O70.0245 (6)0.0162 (5)0.0560 (8)0.0032 (4)−0.0033 (5)−0.0025 (5)
O80.0296 (6)0.0311 (6)0.0500 (7)0.0148 (5)0.0166 (5)0.0097 (5)
N30.0250 (7)0.0154 (6)0.0231 (6)0.0069 (5)0.0047 (5)−0.0009 (4)
N40.0304 (7)0.0214 (6)0.0206 (6)0.0045 (5)0.0023 (5)−0.0065 (5)
C170.0227 (8)0.0210 (7)0.0316 (8)0.0090 (6)−0.0001 (6)0.0003 (6)
C180.0339 (9)0.0307 (9)0.0316 (8)0.0146 (7)−0.0055 (7)−0.0052 (6)
C190.0395 (10)0.0476 (11)0.0269 (8)0.0208 (8)−0.0030 (7)−0.0006 (7)
C200.0297 (9)0.0434 (10)0.0318 (8)0.0131 (8)0.0017 (7)0.0126 (7)
C210.0288 (9)0.0251 (8)0.0383 (9)0.0037 (7)−0.0029 (7)0.0061 (7)
C220.0290 (8)0.0207 (7)0.0277 (7)0.0066 (6)−0.0004 (6)0.0007 (6)
C230.0304 (8)0.0185 (7)0.0218 (7)0.0058 (6)0.0054 (6)−0.0002 (5)
C240.0253 (8)0.0166 (6)0.0183 (6)0.0024 (6)0.0042 (5)0.0014 (5)
C250.0196 (7)0.0128 (6)0.0226 (6)0.0045 (5)0.0040 (5)0.0005 (5)
C260.0241 (8)0.0142 (6)0.0326 (8)0.0040 (6)0.0053 (6)0.0048 (5)
C270.0196 (7)0.0157 (6)0.0207 (6)0.0037 (5)0.0015 (5)−0.0016 (5)
C280.0261 (8)0.0176 (7)0.0296 (7)0.0022 (6)0.0030 (6)−0.0053 (5)
C290.0330 (9)0.0314 (8)0.0273 (8)0.0061 (7)−0.0001 (7)−0.0116 (6)
C300.0314 (9)0.0418 (10)0.0180 (7)0.0108 (7)0.0026 (6)−0.0008 (6)
C310.0297 (9)0.0276 (8)0.0259 (7)0.0036 (7)0.0035 (6)0.0055 (6)
C320.0247 (8)0.0181 (7)0.0231 (7)0.0017 (6)0.0009 (6)−0.0004 (5)

Geometric parameters (Å, °)

Cl1—C41.738 (2)C14—C151.381 (2)
Cl2—C201.7390 (18)C15—C161.387 (2)
S1—O41.4214 (12)C2—H20.9500
S1—N11.6669 (13)C3—H30.9500
S1—C11.7601 (16)C5—H50.9500
S1—O31.4240 (12)C6—H60.9500
S2—O71.4254 (12)C10—H10A0.9800
S2—O81.4186 (14)C10—H10B0.9800
S2—C171.7638 (15)C10—H10C0.9800
S2—N31.6605 (14)C12—H120.9500
F1—C141.3556 (18)C13—H130.9500
F2—C301.3546 (18)C15—H150.9500
O1—C71.2026 (19)C16—H160.9500
O2—C81.208 (2)C17—C221.393 (2)
O5—C231.203 (2)C17—C181.383 (2)
O6—C241.206 (2)C18—C191.386 (2)
N1—C71.4018 (18)C19—C201.384 (3)
N1—C91.4939 (19)C20—C211.376 (2)
N2—C71.378 (2)C21—C221.390 (2)
N2—C81.3666 (19)C24—C251.537 (2)
N2—H2N0.84 (2)C25—C261.5281 (19)
N3—C231.4052 (18)C25—C271.5249 (19)
N3—C251.4996 (19)C27—C321.398 (2)
N4—C231.375 (2)C27—C281.390 (2)
N4—C241.3681 (19)C28—C291.386 (2)
N4—H4N0.875 (19)C29—C301.376 (2)
C1—C61.394 (2)C30—C311.375 (2)
C1—C21.383 (2)C31—C321.390 (2)
C2—C31.387 (2)C18—H180.9500
C3—C41.385 (3)C19—H190.9500
C4—C51.376 (3)C21—H210.9500
C5—C61.388 (2)C22—H220.9500
C8—C91.538 (2)C26—H26A0.9800
C9—C101.5250 (19)C26—H26B0.9800
C9—C111.5254 (19)C26—H26C0.9800
C11—C161.397 (2)C28—H280.9500
C11—C121.391 (2)C29—H290.9500
C12—C131.393 (2)C31—H310.9500
C13—C141.375 (2)C32—H320.9500
O3—S1—O4120.54 (7)H10B—C10—H10C109.00
O3—S1—N1105.32 (7)C9—C10—H10A109.00
O3—S1—C1108.55 (8)C9—C10—H10C109.00
O4—S1—N1107.44 (7)H10A—C10—H10B109.00
O4—S1—C1109.31 (7)C13—C12—H12120.00
N1—S1—C1104.49 (7)C11—C12—H12120.00
O8—S2—N3107.85 (7)C14—C13—H13121.00
O8—S2—C17109.35 (8)C12—C13—H13121.00
N3—S2—C17104.29 (7)C16—C15—H15121.00
O7—S2—C17108.38 (7)C14—C15—H15121.00
O7—S2—O8120.43 (7)C15—C16—H16119.00
O7—S2—N3105.34 (7)C11—C16—H16119.00
C7—N1—C9111.78 (12)S2—C17—C18119.53 (12)
S1—N1—C9124.37 (9)C18—C17—C22121.65 (14)
S1—N1—C7122.81 (11)S2—C17—C22118.78 (11)
C7—N2—C8113.69 (12)C17—C18—C19119.20 (16)
C8—N2—H2N122.9 (14)C18—C19—C20119.16 (16)
C7—N2—H2N123.1 (14)Cl2—C20—C21118.94 (14)
S2—N3—C25124.18 (9)Cl2—C20—C19119.28 (13)
S2—N3—C23123.49 (11)C19—C20—C21121.79 (16)
C23—N3—C25111.33 (12)C20—C21—C22119.53 (15)
C23—N4—C24114.09 (12)C17—C22—C21118.62 (14)
C24—N4—H4N123.3 (13)N3—C23—N4106.55 (13)
C23—N4—H4N122.6 (13)O5—C23—N3126.46 (15)
S1—C1—C6118.72 (12)O5—C23—N4126.98 (14)
C2—C1—C6121.81 (15)O6—C24—N4127.18 (14)
S1—C1—C2119.40 (13)O6—C24—C25125.42 (13)
C1—C2—C3119.02 (17)N4—C24—C25107.39 (13)
C2—C3—C4118.98 (16)N3—C25—C24100.55 (10)
Cl1—C4—C3119.61 (14)C24—C25—C26107.20 (11)
Cl1—C4—C5118.26 (15)C24—C25—C27110.25 (12)
C3—C4—C5122.13 (17)C26—C25—C27115.47 (11)
C4—C5—C6119.27 (17)N3—C25—C26110.75 (12)
C1—C6—C5118.64 (15)N3—C25—C27111.50 (11)
O1—C7—N1126.44 (15)C28—C27—C32118.95 (13)
N1—C7—N2106.47 (12)C25—C27—C28122.38 (12)
O1—C7—N2127.08 (14)C25—C27—C32118.63 (12)
N2—C8—C9107.77 (13)C27—C28—C29120.87 (14)
O2—C8—C9125.18 (13)C28—C29—C30118.37 (15)
O2—C8—N2127.05 (14)F2—C30—C31118.41 (15)
C10—C9—C11115.85 (11)F2—C30—C29118.72 (15)
N1—C9—C8100.25 (10)C29—C30—C31122.88 (15)
N1—C9—C10111.26 (12)C30—C31—C32118.17 (15)
C8—C9—C10107.59 (11)C27—C32—C31120.74 (14)
C8—C9—C11109.55 (12)C17—C18—H18120.00
N1—C9—C11111.12 (11)C19—C18—H18120.00
C12—C11—C16118.98 (13)C18—C19—H19120.00
C9—C11—C16118.47 (12)C20—C19—H19120.00
C9—C11—C12122.52 (12)C20—C21—H21120.00
C11—C12—C13120.71 (14)C22—C21—H21120.00
C12—C13—C14118.31 (14)C17—C22—H22121.00
F1—C14—C15118.21 (15)C21—C22—H22121.00
C13—C14—C15122.95 (14)C25—C26—H26A109.00
F1—C14—C13118.84 (15)C25—C26—H26B109.00
C14—C15—C16117.94 (14)C25—C26—H26C109.00
C11—C16—C15121.08 (13)H26A—C26—H26B110.00
C3—C2—H2120.00H26A—C26—H26C109.00
C1—C2—H2121.00H26B—C26—H26C109.00
C2—C3—H3120.00C27—C28—H28120.00
C4—C3—H3121.00C29—C28—H28120.00
C4—C5—H5120.00C28—C29—H29121.00
C6—C5—H5120.00C30—C29—H29121.00
C1—C6—H6121.00C30—C31—H31121.00
C5—C6—H6121.00C32—C31—H31121.00
C9—C10—H10B109.00C27—C32—H32120.00
H10A—C10—H10C109.00C31—C32—H32120.00
O3—S1—N1—C7169.06 (11)C2—C3—C4—C53.6 (3)
O3—S1—N1—C9−23.58 (13)Cl1—C4—C5—C6177.33 (14)
O4—S1—N1—C739.41 (13)C3—C4—C5—C6−2.1 (3)
O4—S1—N1—C9−153.24 (11)C4—C5—C6—C1−1.6 (3)
C1—S1—N1—C7−76.64 (12)O2—C8—C9—C1163.69 (17)
C1—S1—N1—C990.72 (12)O2—C8—C9—C10−63.03 (18)
O3—S1—C1—C22.56 (16)N2—C8—C9—C11−116.37 (12)
O3—S1—C1—C6179.52 (13)N2—C8—C9—N10.56 (13)
O4—S1—C1—C2135.82 (14)N2—C8—C9—C10116.91 (12)
O4—S1—C1—C6−47.21 (15)O2—C8—C9—N1−179.38 (13)
N1—S1—C1—C2−109.44 (14)C8—C9—C11—C12−133.46 (14)
N1—S1—C1—C667.53 (14)C8—C9—C11—C1648.46 (17)
O7—S2—N3—C23168.37 (12)C10—C9—C11—C12−11.6 (2)
O7—S2—N3—C25−24.06 (13)C10—C9—C11—C16170.35 (14)
O8—S2—N3—C2338.58 (13)N1—C9—C11—C12116.69 (15)
O8—S2—N3—C25−153.85 (11)N1—C9—C11—C16−61.39 (17)
C17—S2—N3—C23−77.60 (13)C9—C11—C12—C13−176.64 (15)
C17—S2—N3—C2589.98 (12)C12—C11—C16—C15−0.9 (2)
O7—S2—C17—C18−0.26 (17)C16—C11—C12—C131.4 (2)
O7—S2—C17—C22177.31 (13)C9—C11—C16—C15177.24 (14)
O8—S2—C17—C18132.76 (15)C11—C12—C13—C14−0.5 (2)
O8—S2—C17—C22−49.67 (16)C12—C13—C14—C15−1.1 (3)
N3—S2—C17—C18−112.11 (15)C12—C13—C14—F1178.57 (15)
N3—S2—C17—C2265.46 (15)C13—C14—C15—C161.6 (3)
S1—N1—C9—C8−170.14 (9)F1—C14—C15—C16−178.08 (15)
S1—N1—C9—C1076.29 (14)C14—C15—C16—C11−0.6 (2)
S1—N1—C9—C11−54.40 (15)S2—C17—C18—C19175.79 (15)
S1—N1—C7—O1−8.4 (2)C22—C17—C18—C19−1.7 (3)
S1—N1—C7—N2170.79 (9)S2—C17—C22—C21−174.77 (13)
C9—N1—C7—O1−177.21 (14)C18—C17—C22—C212.8 (3)
C9—N1—C7—N22.00 (15)C17—C18—C19—C20−0.7 (3)
C7—N1—C9—C8−1.56 (14)C18—C19—C20—Cl2−177.81 (15)
C7—N1—C9—C10−115.13 (13)C18—C19—C20—C212.0 (3)
C7—N1—C9—C11114.18 (13)Cl2—C20—C21—C22178.86 (14)
C7—N2—C8—O2−179.43 (14)C19—C20—C21—C22−1.0 (3)
C7—N2—C8—C90.64 (16)C20—C21—C22—C17−1.4 (3)
C8—N2—C7—O1177.57 (14)O6—C24—C25—N3178.72 (13)
C8—N2—C7—N1−1.63 (16)O6—C24—C25—C26−65.50 (18)
C25—N3—C23—O5−178.52 (14)O6—C24—C25—C2760.94 (18)
S2—N3—C23—O5−9.5 (2)N4—C24—C25—N3−2.26 (13)
S2—N3—C23—N4169.79 (10)N4—C24—C25—C26113.52 (13)
C23—N3—C25—C27117.74 (12)N4—C24—C25—C27−120.04 (12)
C25—N3—C23—N40.80 (15)N3—C25—C27—C28111.40 (15)
S2—N3—C25—C24−168.02 (9)N3—C25—C27—C32−66.12 (17)
S2—N3—C25—C2678.89 (14)C24—C25—C27—C28−137.80 (14)
S2—N3—C25—C27−51.16 (15)C24—C25—C27—C3244.67 (18)
C23—N3—C25—C240.88 (14)C26—C25—C27—C28−16.1 (2)
C23—N3—C25—C26−112.22 (13)C26—C25—C27—C32166.34 (14)
C23—N4—C24—O6−177.93 (14)C25—C27—C28—C29−176.22 (15)
C24—N4—C23—O5176.83 (14)C32—C27—C28—C291.3 (2)
C24—N4—C23—N3−2.48 (16)C25—C27—C32—C31176.65 (15)
C23—N4—C24—C253.07 (16)C28—C27—C32—C31−1.0 (2)
S1—C1—C2—C3174.66 (14)C27—C28—C29—C30−0.1 (3)
C2—C1—C6—C53.8 (3)C28—C29—C30—F2178.10 (16)
C6—C1—C2—C3−2.2 (3)C28—C29—C30—C31−1.4 (3)
S1—C1—C6—C5−173.13 (13)F2—C30—C31—C32−177.78 (15)
C1—C2—C3—C4−1.5 (3)C29—C30—C31—C321.8 (3)
C2—C3—C4—Cl1−175.76 (15)C30—C31—C32—C27−0.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2N···O5i0.84 (2)2.23 (2)2.9383 (17)143.0 (18)
N4—H4N···O1i0.875 (19)2.103 (19)2.8595 (17)144.4 (17)
C6—H6···O6ii0.952.533.339 (2)143
C16—H16···O7iii0.952.383.2330 (18)149
C26—H26C···O4iv0.982.413.358 (2)162
C32—H32···O3v0.952.383.2715 (19)155
C3—H3···F1vi0.952.763.308 (2)118
C29—H29···F1vii0.952.663.3715 (19)133
C13—H13···F2vii0.952.753.4627 (19)133
C19—H19···F2vii0.952.693.223 (2)116

Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y−1, z; (iii) x, y−1, z; (iv) x−1, y+1, z; (v) x−1, y, z; (vi) −x+2, −y, −z+1; (vii) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2138).

References

  • Ahmad, I., Hameed, S., Duddeck, H., Lenzen, S., Rustenbeck, I. & Ahmad, R. (2002). Z. Naturforsch. Teil B, 57, 349–354.
  • Ahmad, R., Jabeen, R., Zia-ul-Haq, M., Nadeem, H., Duddeck, H. & Verspohl, E. J. (2000). Z. Naturforsch. Teil B, 55, 203–207.
  • Flosi, W. J., DeGoey, D. A., Grampovnik, D. J., Chen, H., Klein, L. L., Dekhtyar, T., Masse, S., Marsh, K. C., Mo, H. M. & Kemp, V. (2006). Bioorg. Med. Chem.14, 6695–6712. [PubMed]
  • Kashif, M. K., Ahmad, I. & Hameed, S. (2008). ARKIVOC, xvi, 311–317.
  • Kashif, M. K., Hussain, A., Khawar Rauf, M., Ebihara, M. & Hameed, S. (2008). Acta Cryst. E64, o444. [PMC free article] [PubMed]
  • Kato, K., Nakayama, K., Mizota, M., Miwa, I. & Okuda, J. (1991). Chem. Pharm. Bull.39, 1540–1545. [PubMed]
  • Kato, K., Nakayama, K., Ohta, M., Murakami, N., Murakami, K., Mizota, M., Miwa, I. & Okuda, J. (1991). Eur. J. Pharm.193, 185–191. [PubMed]
  • Muccioli, G. G., Fazio, N., Scriba, G. K. E., Poppitz, W., Cannata, F., Poupaert, J. H., Wouters, J. & Lambert, D. M. (2006). J. Med. Chem.49, 417–425. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Stoe & Cie (2006). X-AREA and X-RED32 Stoe & Cie GmbH, Darmstadt, Germany.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography