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Acta Cryst. (2008). E64, o2304    [ doi:10.1107/S1600536808035824 ]

Phenyl naphthalene-2-sulfonate

J. P. Vennila, H. P. Kavitha, D. J. Thiruvadigal and V. Manivannan

Abstract top

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...[pi] interactions.

Comment top

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.

Related literature top

For general background, see: Spungin et al. (1984); Yachi et al. (1989). For related structures, see: Manivannan et al. (2005); Ramachandran et al. (2007). Cg1 is the centroid of the C1–C6 ring, Cg2 is the centroid of the C7–C9/C14–C16 ring and Cg3 is the centroid of the C9–C14 ring.

Experimental top

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 top

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

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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.
Phenyl naphthalene-2-sulfonate top
Crystal data top
C16H12O3SF(000) = 592
Mr = 284.32Dx = 1.389 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4818 reflections
a = 6.1525 (2) Åθ = 2.2–25.4°
b = 12.7466 (7) ŵ = 0.24 mm−1
c = 17.3414 (10) ÅT = 295 K
V = 1359.97 (12) Å3Tablet, colourless
Z = 40.25 × 0.18 × 0.16 mm
Data collection top
Bruker Kappa APEXII
diffractometer		5093 independent reflections
Radiation source: fine-focus sealed tube3412 reflections with I > 2σ(I)
graphiteRint = 0.027
ω and φ scansθmax = 34.9°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→5
Tmin = 0.942, Tmax = 0.962k = −19→18
11868 measured reflectionsl = −25→27
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0476P)2 + 0.0596P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
5093 reflectionsΔρmax = 0.26 e Å−3
181 parametersΔρmin = −0.31 e Å−3
0 restraintsAbsolute structure: Flack (1983), 1993 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.03 (7)
Crystal data top
C16H12O3SV = 1359.97 (12) Å3
Mr = 284.32Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.1525 (2) ŵ = 0.24 mm−1
b = 12.7466 (7) ÅT = 295 K
c = 17.3414 (10) Å0.25 × 0.18 × 0.16 mm
Data collection top
Bruker Kappa APEXII
diffractometer		3412 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.027
Tmin = 0.942, Tmax = 0.962θmax = 34.9°
11868 measured reflectionsStandard reflections: 0
5093 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.106Δρmax = 0.26 e Å−3
S = 1.01Δρmin = −0.31 e Å−3
5093 reflectionsAbsolute structure: Flack (1983), 1993 Friedel pairs
181 parametersFlack parameter: −0.03 (7)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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

references
References top

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