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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): o640.
Published online 2008 February 29. doi:  10.1107/S1600536808005370
PMCID: PMC2960772

4-(3-Nitro­phen­yl)-3-(phenyl­sulfon­yl)but-3-en-2-one

Abstract

The C=C double bond in the title mol­ecule, C16H13NO5S, has an E configuration. The crystal structure is stabilized by C—H(...)O hydrogen bonds. There is also a weak C—H(...)π-ring inter­action in the structure.

Related literature

For related literature, see: Pei (1998 [triangle]). For the chemical preparation, see: Wada et al. (1996 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o640-scheme1.jpg

Experimental

Crystal data

  • C16H13NO5S
  • M r = 331.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o640-efi1.jpg
  • a = 7.957 (2) Å
  • b = 10.580 (3) Å
  • c = 18.271 (6) Å
  • β = 95.976 (14)°
  • V = 1529.7 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 298 (1) K
  • 0.25 × 0.20 × 0.20 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.923, T max = 0.954
  • 14836 measured reflections
  • 3507 independent reflections
  • 2890 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.106
  • S = 1.05
  • 3507 reflections
  • 210 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.40 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 [triangle]); program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: CrystalStructure.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005370/fb2081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005370/fb2081Isup2.hkl

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

Acknowledgments

This work was supported by the Open Foundation of the Key Discipline of Industrial Catalysis.

supplementary crystallographic information

Comment

Phenylsulfonyl-3-alken-2-ones have been used as asymmetric synthetic reagents (Wada et al., 1996) as well as electron-deficient dienophiles. They have been applied in asymmetric Diels–Alder chemistry (Pei, 1998). The title compound has been prepared and studied in order to get a better understanding about the synthesis of phenylsulfonyl-3-alken-2-ones. The molecular structure, Fig. 1, shows that an E-configuration is present on the C=C double bond between the atoms C1 and C4. There is also present a C—H···π-electron ring interaction in the structure. It involves the phenyl ring C11–C16 with centroid Cg1 (Table 1).

Experimental

The title compound was prepared according to the procedure of Wada et al. (1996). Diffraction quality crystals were obtained by recrystallization from ethanol solution by slow evaporation at room temperature. The average dimension of the block crystals was about 0.2 mm.

Refinement

All the H atoms were discerned in the difference Fourier map. Nevertheless, the H atoms were positioned into the idealized positions and their parameters were constrained in riding-mode approximation. The constraints: C—Haryl,alkenyl)=0.93 and C—Hmethyl=0.96 Å. Uiso(Haryl,Halkenyl)= 1.2Ueq(Caryl,Calkenyl) and Uiso(Hmetyl)=1.5Ueq(Cmethyl).

Figures

Fig. 1.
View of the title molecule showing the atom labelling scheme. The displacement ellipsoids are drawn at the 40% probability level.

Crystal data

C16H13NO5SF000 = 688.00
Mr = 331.34Dx = 1.439 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71075 Å
Hall symbol: -P 2ynCell parameters from 12472 reflections
a = 7.957 (2) Åθ = 3.2–27.5º
b = 10.580 (3) ŵ = 0.24 mm1
c = 18.271 (6) ÅT = 298 (1) K
β = 95.976 (14)ºBlock, colourless
V = 1529.7 (8) Å30.25 × 0.20 × 0.20 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer3507 independent reflections
Monochromator: graphite2890 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.027
T = 285 Kθmax = 27.5º
ω scansθmin = 3.2º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)h = −8→10
Tmin = 0.923, Tmax = 0.954k = −13→13
14836 measured reflectionsl = −23→23

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.106  w = 1/[σ2(Fo2) + (0.0516P)2 + 0.4387P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
3507 reflectionsΔρmax = 0.34 e Å3
210 parametersΔρmin = −0.40 e Å3
42 constraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0097 (17)

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.84122 (5)0.43647 (4)0.25330 (2)0.03894 (14)
O10.99494 (16)0.40871 (14)0.10399 (8)0.0607 (4)
O20.02708 (17)0.12269 (16)0.11304 (9)0.0674 (4)
O3−0.02286 (17)0.14516 (19)−0.00423 (9)0.0806 (5)
O40.89564 (17)0.56378 (11)0.24210 (8)0.0568 (4)
O50.72060 (15)0.41361 (14)0.30472 (7)0.0566 (4)
N10.07214 (18)0.14380 (15)0.05295 (9)0.0508 (4)
C10.75310 (18)0.37984 (14)0.16622 (8)0.0349 (3)
C20.8455 (2)0.42725 (15)0.10363 (9)0.0418 (4)
C30.7499 (3)0.5076 (2)0.04658 (14)0.0770 (7)
H310.81050.51210.00390.116*
H320.73710.59100.06590.116*
H330.64040.47130.03320.116*
C40.61399 (18)0.30895 (15)0.16516 (8)0.0370 (3)
H40.57390.29560.21060.044*
C50.51608 (18)0.24949 (14)0.10202 (8)0.0357 (3)
C60.34611 (19)0.22278 (15)0.10721 (9)0.0376 (3)
H60.29740.24060.15020.045*
C70.25178 (19)0.16961 (15)0.04761 (9)0.0385 (3)
C80.3182 (2)0.13919 (17)−0.01672 (9)0.0473 (4)
H80.25070.1052−0.05650.057*
C90.4884 (2)0.16088 (19)−0.02025 (10)0.0526 (4)
H90.53740.1386−0.06250.063*
C100.5862 (2)0.21504 (17)0.03795 (10)0.0462 (4)
H100.70050.22890.03460.055*
C111.02028 (18)0.34291 (15)0.28003 (8)0.0369 (3)
C121.1754 (2)0.40079 (18)0.29545 (9)0.0453 (4)
H121.18830.48670.28680.054*
C131.3113 (2)0.3282 (2)0.32406 (11)0.0590 (5)
H131.41680.36540.33500.071*
C141.2909 (3)0.2017 (2)0.33632 (12)0.0655 (6)
H141.38240.15380.35630.079*
C151.1369 (3)0.1452 (2)0.31942 (13)0.0658 (6)
H151.12520.05890.32710.079*
C160.9995 (2)0.21509 (17)0.29120 (11)0.0524 (4)
H160.89470.17700.27990.063*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0325 (2)0.0432 (2)0.0403 (2)0.00241 (15)−0.00025 (15)−0.00634 (16)
O10.0424 (7)0.0742 (9)0.0676 (9)−0.0004 (6)0.0163 (6)0.0104 (7)
O20.0468 (7)0.0850 (11)0.0725 (10)−0.0159 (7)0.0157 (7)−0.0016 (8)
O30.0393 (7)0.1266 (15)0.0713 (10)0.0022 (8)−0.0154 (7)−0.0245 (10)
O40.0583 (8)0.0375 (6)0.0717 (9)0.0017 (5)−0.0075 (7)−0.0083 (6)
O50.0395 (6)0.0887 (10)0.0420 (7)0.0056 (6)0.0062 (5)−0.0108 (6)
N10.0348 (7)0.0560 (9)0.0606 (10)−0.0022 (6)0.0003 (7)−0.0121 (7)
C10.0321 (7)0.0371 (7)0.0346 (7)0.0026 (6)−0.0009 (6)0.0016 (6)
C20.0411 (8)0.0418 (8)0.0423 (9)−0.0043 (7)0.0038 (7)0.0017 (6)
C30.0709 (14)0.0856 (16)0.0746 (15)0.0032 (12)0.0080 (12)0.0424 (13)
C40.0335 (7)0.0425 (8)0.0344 (7)0.0013 (6)0.0012 (6)0.0035 (6)
C50.0325 (7)0.0384 (7)0.0355 (7)0.0008 (6)0.0004 (6)0.0036 (6)
C60.0345 (7)0.0437 (8)0.0348 (8)−0.0007 (6)0.0047 (6)0.0001 (6)
C70.0319 (7)0.0412 (8)0.0413 (8)0.0020 (6)−0.0006 (6)0.0001 (6)
C80.0476 (9)0.0549 (10)0.0377 (8)0.0027 (8)−0.0039 (7)−0.0071 (7)
C90.0516 (10)0.0671 (12)0.0406 (9)0.0026 (9)0.0128 (8)−0.0096 (8)
C100.0356 (8)0.0568 (10)0.0472 (9)0.0010 (7)0.0086 (7)−0.0031 (8)
C110.0317 (7)0.0447 (8)0.0336 (7)0.0004 (6)0.0004 (6)−0.0030 (6)
C120.0347 (8)0.0575 (10)0.0435 (9)−0.0072 (7)0.0031 (7)−0.0021 (7)
C130.0308 (8)0.0930 (16)0.0526 (11)0.0023 (9)0.0016 (7)−0.0053 (10)
C140.0525 (11)0.0838 (15)0.0587 (12)0.0304 (11)−0.0011 (9)−0.0044 (11)
C150.0724 (14)0.0492 (11)0.0744 (14)0.0161 (10)0.0006 (11)−0.0012 (9)
C160.0471 (10)0.0451 (9)0.0633 (11)−0.0017 (7)−0.0020 (8)−0.0047 (8)

Geometric parameters (Å, °)

S1—O51.4317 (13)C6—H60.9300
S1—O41.4360 (13)C7—C81.376 (2)
S1—C111.7617 (16)C8—C91.382 (3)
S1—C11.7747 (16)C8—H80.9300
O1—C21.204 (2)C9—C101.375 (2)
O2—N11.211 (2)C9—H90.9300
O3—N11.224 (2)C10—H100.9300
N1—C71.468 (2)C11—C161.380 (2)
C1—C41.335 (2)C11—C121.381 (2)
C1—C21.508 (2)C12—C131.384 (3)
C2—C31.491 (3)C12—H120.9300
C3—H310.9600C13—C141.369 (3)
C3—H320.9600C13—H130.9300
C3—H330.9600C14—C151.369 (3)
C4—C51.465 (2)C14—H140.9300
C4—H40.9300C15—C161.375 (3)
C5—C61.394 (2)C15—H150.9300
C5—C101.396 (2)C16—H160.9300
C6—C71.377 (2)
O5—S1—O4118.99 (9)C8—C7—C6123.02 (15)
O5—S1—C11107.53 (8)C8—C7—N1118.44 (14)
O4—S1—C11108.63 (8)C6—C7—N1118.54 (14)
O5—S1—C1107.57 (8)C7—C8—C9117.81 (15)
O4—S1—C1106.61 (8)C7—C8—H8121.1
C11—S1—C1106.95 (7)C9—C8—H8121.1
O2—N1—O3124.14 (16)C10—C9—C8120.74 (16)
O2—N1—C7118.48 (15)C10—C9—H9119.6
O3—N1—C7117.38 (16)C8—C9—H9119.6
C4—C1—C2130.13 (14)C9—C10—C5120.92 (15)
C4—C1—S1116.88 (12)C9—C10—H10119.5
C2—C1—S1112.89 (11)C5—C10—H10119.5
O1—C2—C3121.90 (17)C16—C11—C12121.53 (15)
O1—C2—C1120.05 (15)C16—C11—S1119.05 (12)
C3—C2—C1117.76 (16)C12—C11—S1119.18 (13)
C2—C3—H31109.5C11—C12—C13118.54 (18)
C2—C3—H32109.5C11—C12—H12120.7
H31—C3—H32109.5C13—C12—H12120.7
C2—C3—H33109.5C14—C13—C12120.20 (18)
H31—C3—H33109.5C14—C13—H13119.9
H32—C3—H33109.5C12—C13—H13119.9
C1—C4—C5128.65 (14)C15—C14—C13120.55 (18)
C1—C4—H4115.7C15—C14—H14119.7
C5—C4—H4115.7C13—C14—H14119.7
C6—C5—C10118.61 (14)C14—C15—C16120.5 (2)
C6—C5—C4118.26 (14)C14—C15—H15119.7
C10—C5—C4123.10 (14)C16—C15—H15119.7
C7—C6—C5118.80 (14)C15—C16—C11118.64 (18)
C7—C6—H6120.6C15—C16—H16120.7
C5—C6—H6120.6C11—C16—H16120.7
O4—S1—C1—C236.47 (12)C4—C1—C2—C358.5 (2)
O4—S1—C1—C4−140.16 (11)C1—C4—C5—C6−155.46 (15)
O4—S1—C11—C128.06 (15)C1—C4—C5—C1026.5 (2)
O4—S1—C11—C16−177.55 (14)C4—C5—C6—C7178.54 (13)
O5—S1—C1—C2165.12 (10)C4—C5—C10—C9−179.12 (15)
O5—S1—C1—C4−11.50 (13)C6—C5—C10—C92.9 (2)
O5—S1—C11—C12−121.99 (13)C10—C5—C6—C7−3.4 (2)
O5—S1—C11—C1652.59 (15)C5—C6—C7—N1−178.84 (13)
C1—S1—C11—C12122.77 (13)C5—C6—C7—C81.3 (2)
C1—S1—C11—C16−62.81 (15)N1—C7—C8—C9−178.34 (14)
C11—S1—C1—C2−79.59 (11)C6—C7—C8—C91.6 (2)
C11—S1—C1—C4103.79 (12)C7—C8—C9—C10−2.2 (2)
O2—N1—C7—C6−28.2 (2)C8—C9—C10—C5−0.0 (2)
O2—N1—C7—C8151.86 (15)S1—C11—C12—C13173.00 (13)
O3—N1—C7—C6151.83 (16)S1—C11—C16—C15−173.37 (15)
O3—N1—C7—C8−28.2 (2)C12—C11—C16—C151.0 (2)
S1—C1—C2—O156.37 (18)C16—C11—C12—C13−1.3 (2)
S1—C1—C2—C3−117.54 (15)C11—C12—C13—C140.2 (2)
S1—C1—C4—C5−179.53 (12)C12—C13—C14—C151.0 (3)
C2—C1—C4—C54.5 (2)C13—C14—C15—C16−1.3 (3)
C4—C1—C2—O1−127.56 (18)C14—C15—C16—C110.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···O4i0.932.603.104 (2)114
C8—H8···O5ii0.932.533.321 (2)143
C10—H10···O3iii0.932.543.364 (2)148
C13—H13···O5iii0.932.593.433 (2)152
C12—H12···O40.932.522.903 (2)105
C16—H16···O4i0.932.603.524 (2)176
C9—H9···Cg1ii0.932.803.608 (2)145

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2081).

References

  • Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Pei, W. (1998). Chem. J. Chin. Univ.19, 402–404.
  • Rigaku (1998). PROCESS-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2004). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wada, E., Pei, W., Yasuoka, H., Chin, U. & Kanemasa, S. (1996). Tetrahedron, 52, 1205–1220.

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