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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2304.
Published online 2008 November 8. doi:  10.1107/S1600536808035824
PMCID: PMC2959821

Phenyl naphthalene-2-sulfonate

Abstract

In the crystal structure of the title compound, C16H12O3S, the dihedral angle between the naphthalene ring system and the phenyl ring is 65.21 (3)°. The mol­ecules are linked by inter­molecular C—H(...)O hydrogen bonds, forming a chain along the a axis. The chains are connected through weak C—H(...)π inter­actions.

Related literature

For general background, see: Spungin et al. (1984 [triangle]); Yachi et al. (1989 [triangle]). For related structures, see: Manivannan et al. (2005 [triangle]); Ramachandran et al. (2007 [triangle]).

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Object name is e-64-o2304-scheme1.jpg

Experimental

Crystal data

  • C16H12O3S
  • M r = 284.32
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2304-efi1.jpg
  • a = 6.1525 (2) Å
  • b = 12.7466 (7) Å
  • c = 17.3414 (10) Å
  • V = 1359.97 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 295 (2) K
  • 0.25 × 0.18 × 0.16 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.942, T max = 0.962
  • 11868 measured reflections
  • 5093 independent reflections
  • 3412 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.106
  • S = 1.01
  • 5093 reflections
  • 181 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.31 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1993 Friedel pairs
  • Flack parameter: −0.03 (7)

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035824/is2352sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035824/is2352Isup2.hkl

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

Acknowledgments

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

supplementary crystallographic information

Comment

Several compounds containing the para -toluene sulfonate moiety are used in the fields of biology and industry. The merging of lipids can be monitored using a derivative of para-toluene sulfonate (Yachi et al., 1989). This method has been used in studying the membrane fusion during the acrosome reaction (Spungin et al., 1984).

The geometric parameters in the title compound (I) agree well with the reported values of similar structures (Manivannan et al., 2005; Ramachandran et al., 2007). The phenyl ring makes a dihedral angle of 65.21 (3)° with the naphthalene ring system. The torsion angles of O2—S1—C7—C8 and O3—S1—C7—C16 [2.04 (15)° and 46.94 (15)°, respectively] indicate the syn conformation of the sulfonyl moiety. The crystal structure is stabilized through weak intermolecular C—H···O and C—H···π interactions (Fig. 2 and Table 1). Cg1, Cg2 and Cg3 are the centroids of the C1–C6 ring, the C7–C9/C14–C16 ring and the C9–C14 ring, respectively.

Experimental

2-Naphthalene sulfonyl chloride (2.5 mmol) dissolved in acetone (4 ml) was added dropwise to phenol (2.5 mmol) in aqueous NaOH solution (4 ml, 5%) with constant shaking. The precipitated compound (2 mmol, yield 77%) recrystallized from ethanol yielded colourless crystals.

Refinement

H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for the sake of clarity.

Crystal data

C16H12O3SF000 = 592
Mr = 284.32Dx = 1.389 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4818 reflections
a = 6.1525 (2) Åθ = 2.2–25.4º
b = 12.7466 (7) ŵ = 0.24 mm1
c = 17.3414 (10) ÅT = 295 (2) K
V = 1359.97 (12) Å3Tablet, colourless
Z = 40.25 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer5093 independent reflections
Radiation source: fine-focus sealed tube3412 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 295(2) Kθmax = 34.9º
ω and [var phi] scansθmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −9→5
Tmin = 0.942, Tmax = 0.962k = −19→18
11868 measured reflectionsl = −25→27

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044  w = 1/[σ2(Fo2) + (0.0476P)2 + 0.0596P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.106(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.26 e Å3
5093 reflectionsΔρmin = −0.31 e Å3
181 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1993 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.03 (7)

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

xyzUiso*/Ueq
S10.68361 (7)0.89579 (3)0.10630 (3)0.03997 (11)
O10.8255 (2)0.88973 (9)0.18279 (6)0.0403 (3)
O20.4945 (2)0.95689 (12)0.12058 (8)0.0527 (4)
O30.6661 (3)0.78918 (10)0.08397 (9)0.0646 (4)
C10.8523 (3)0.98154 (12)0.22766 (9)0.0332 (3)
C21.0472 (3)1.03331 (16)0.22378 (11)0.0438 (4)
H21.15571.01140.19010.053*
C31.0781 (3)1.11934 (17)0.27152 (13)0.0537 (5)
H31.20891.15580.27010.064*
C40.9168 (3)1.15065 (16)0.32060 (12)0.0513 (5)
H40.93891.20840.35240.062*
C50.7234 (3)1.09789 (16)0.32342 (10)0.0497 (5)
H50.61441.12030.35670.060*
C60.6895 (3)1.01146 (14)0.27702 (10)0.0422 (4)
H60.55940.97440.27920.051*
C70.8516 (3)0.96307 (12)0.04171 (9)0.0334 (3)
C80.7855 (3)1.05729 (12)0.01241 (9)0.0355 (4)
H80.65221.08550.02690.043*
C90.9203 (3)1.11168 (13)−0.03991 (10)0.0380 (4)
C100.8568 (4)1.20865 (14)−0.07297 (12)0.0522 (5)
H100.72311.2379−0.06010.063*
C110.9892 (5)1.25888 (17)−0.12299 (12)0.0652 (6)
H110.94581.3223−0.14460.078*
C121.1911 (5)1.2161 (2)−0.14254 (12)0.0709 (7)
H121.28081.2516−0.17690.085*
C131.2580 (3)1.12340 (18)−0.11191 (12)0.0569 (5)
H131.39331.0963−0.12510.068*
C141.1230 (3)1.06801 (14)−0.06014 (10)0.0405 (4)
C151.1837 (3)0.96940 (15)−0.02884 (10)0.0439 (4)
H151.31640.9399−0.04250.053*
C161.0520 (3)0.91760 (13)0.02050 (10)0.0395 (4)
H161.09290.85270.04030.047*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0443 (2)0.0406 (2)0.0350 (2)−0.00821 (18)0.00007 (19)−0.00279 (17)
O10.0525 (7)0.0344 (5)0.0339 (6)0.0047 (6)−0.0012 (5)0.0021 (5)
O20.0361 (7)0.0768 (9)0.0451 (8)−0.0027 (6)0.0010 (6)0.0017 (7)
O30.0897 (11)0.0457 (7)0.0584 (9)−0.0245 (7)0.0029 (9)−0.0083 (6)
C10.0381 (10)0.0353 (7)0.0262 (7)0.0012 (6)−0.0017 (6)0.0046 (6)
C20.0352 (10)0.0579 (11)0.0382 (9)0.0016 (8)0.0018 (7)−0.0005 (8)
C30.0463 (12)0.0649 (13)0.0498 (12)−0.0151 (10)−0.0042 (9)−0.0019 (10)
C40.0665 (14)0.0508 (11)0.0365 (11)−0.0090 (9)−0.0024 (9)−0.0056 (8)
C50.0563 (13)0.0562 (11)0.0366 (9)−0.0022 (9)0.0132 (8)−0.0060 (9)
C60.0413 (10)0.0503 (9)0.0348 (8)−0.0094 (8)0.0053 (8)0.0016 (7)
C70.0373 (9)0.0340 (7)0.0290 (7)−0.0004 (6)−0.0011 (6)−0.0049 (6)
C80.0374 (9)0.0343 (7)0.0348 (8)0.0011 (7)−0.0017 (7)−0.0063 (6)
C90.0478 (10)0.0338 (8)0.0325 (8)−0.0053 (7)−0.0064 (7)−0.0034 (7)
C100.0675 (14)0.0375 (9)0.0516 (11)−0.0044 (8)−0.0138 (10)0.0012 (8)
C110.0953 (18)0.0482 (11)0.0521 (14)−0.0225 (12)−0.0208 (13)0.0102 (9)
C120.0927 (18)0.0760 (15)0.0440 (12)−0.0440 (15)−0.0050 (13)0.0084 (11)
C130.0562 (12)0.0748 (13)0.0396 (10)−0.0233 (10)0.0020 (8)−0.0062 (10)
C140.0419 (11)0.0515 (10)0.0280 (8)−0.0102 (8)−0.0035 (7)−0.0074 (7)
C150.0378 (10)0.0594 (10)0.0347 (9)0.0062 (9)−0.0008 (8)−0.0070 (8)
C160.0451 (10)0.0425 (9)0.0310 (9)0.0101 (7)−0.0023 (7)−0.0024 (7)

Geometric parameters (Å, °)

S1—O31.4172 (13)C7—C161.411 (2)
S1—O21.4217 (15)C8—C91.411 (2)
S1—O11.5899 (13)C8—H80.9300
S1—C71.7487 (17)C9—C141.410 (3)
O1—C11.4149 (19)C9—C101.417 (2)
C1—C21.370 (2)C10—C111.351 (3)
C1—C61.372 (2)C10—H100.9300
C2—C31.387 (3)C11—C121.398 (4)
C2—H20.9300C11—H110.9300
C3—C41.367 (3)C12—C131.360 (3)
C3—H30.9300C12—H120.9300
C4—C51.368 (3)C13—C141.412 (3)
C4—H40.9300C13—H130.9300
C5—C61.380 (3)C14—C151.419 (3)
C5—H50.9300C15—C161.351 (3)
C6—H60.9300C15—H150.9300
C7—C81.366 (2)C16—H160.9300
O3—S1—O2120.72 (10)C7—C8—C9119.74 (16)
O3—S1—O1102.89 (9)C7—C8—H8120.1
O2—S1—O1109.31 (7)C9—C8—H8120.1
O3—S1—C7109.88 (9)C14—C9—C8119.07 (16)
O2—S1—C7109.05 (8)C14—C9—C10119.18 (18)
O1—S1—C7103.52 (7)C8—C9—C10121.74 (17)
C1—O1—S1118.86 (10)C11—C10—C9120.4 (2)
C2—C1—C6122.41 (16)C11—C10—H10119.8
C2—C1—O1118.25 (15)C9—C10—H10119.8
C6—C1—O1119.20 (15)C10—C11—C12120.4 (2)
C1—C2—C3118.10 (17)C10—C11—H11119.8
C1—C2—H2121.0C12—C11—H11119.8
C3—C2—H2121.0C13—C12—C11120.9 (2)
C4—C3—C2120.22 (18)C13—C12—H12119.6
C4—C3—H3119.9C11—C12—H12119.6
C2—C3—H3119.9C12—C13—C14120.3 (2)
C3—C4—C5120.68 (18)C12—C13—H13119.8
C3—C4—H4119.7C14—C13—H13119.8
C5—C4—H4119.7C9—C14—C13118.75 (19)
C4—C5—C6120.22 (17)C9—C14—C15119.15 (17)
C4—C5—H5119.9C13—C14—C15122.09 (19)
C6—C5—H5119.9C16—C15—C14121.17 (18)
C1—C6—C5118.37 (17)C16—C15—H15119.4
C1—C6—H6120.8C14—C15—H15119.4
C5—C6—H6120.8C15—C16—C7119.23 (16)
C8—C7—C16121.62 (16)C15—C16—H16120.4
C8—C7—S1119.58 (13)C7—C16—H16120.4
C16—C7—S1118.80 (12)
O3—S1—O1—C1−171.58 (12)S1—C7—C8—C9−179.81 (12)
O2—S1—O1—C1−42.13 (14)C7—C8—C9—C14−0.9 (2)
C7—S1—O1—C173.97 (13)C7—C8—C9—C10178.76 (16)
S1—O1—C1—C2−104.08 (16)C14—C9—C10—C11−0.3 (3)
S1—O1—C1—C680.26 (17)C8—C9—C10—C11−179.92 (18)
C6—C1—C2—C3−0.4 (3)C9—C10—C11—C12−0.3 (3)
O1—C1—C2—C3−175.92 (16)C10—C11—C12—C130.2 (3)
C1—C2—C3—C4−0.1 (3)C11—C12—C13—C140.6 (3)
C2—C3—C4—C50.0 (3)C8—C9—C14—C13−179.35 (16)
C3—C4—C5—C60.6 (3)C10—C9—C14—C131.0 (2)
C2—C1—C6—C51.0 (3)C8—C9—C14—C151.5 (2)
O1—C1—C6—C5176.47 (15)C10—C9—C14—C15−178.11 (16)
C4—C5—C6—C1−1.1 (3)C12—C13—C14—C9−1.2 (3)
O3—S1—C7—C8132.35 (14)C12—C13—C14—C15177.93 (18)
O2—S1—C7—C8−2.04 (15)C9—C14—C15—C16−0.8 (3)
O1—S1—C7—C8−118.32 (13)C13—C14—C15—C16−179.89 (18)
O3—S1—C7—C16−46.94 (15)C14—C15—C16—C7−0.6 (3)
O2—S1—C7—C16178.67 (12)C8—C7—C16—C151.3 (2)
O1—S1—C7—C1662.39 (13)S1—C7—C16—C15−179.43 (14)
C16—C7—C8—C9−0.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.932.513.424 (2)169
C5—H5···Cg2ii0.932.963.486 (2)117
C6—H6···Cg3ii0.932.943.535 (2)123
C12—H12···Cg1iii0.932.943.788 (3)152

Symmetry codes: (i) x+1, y, z; (ii) −x+3/2, −y+2, z+1/2; (iii) −x, y+5/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2352).

References

  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Manivannan, V., Vembu, N., Nallu, M., Sivakumar, K. & Fronczek, F. R. (2005). Acta Cryst. E61, o239–o241.
  • Ramachandran, G., Kanakam, C. C., Manivannan, V., Thiruvenkatam, V. & Row, T. N. G. (2007). Acta Cryst. E63, o4638.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Spungin, B., Levinshal, T., Rubenstein, S. & Breitbart, H. (1984). Biochim. Biophys. Acta, 769, 531–542.
  • Yachi, K., Sugiyama, Y., Sawada, Y., Iga, T., Ikeda, Y., Toda, G. & Hananon, M. (1989). Biochim. Biophys. Acta, 978, 1–7. [PubMed]

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