Phenyl naphthalene-2-sulfonate

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

doi:10.1107/S1600536808035824

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2304

doi:10.1107/S1600536808035824

Open

access

Phenyl naphthalene-2-sulfonate

Jasmine P. Vennila,^a Helen P. Kavitha,^b D. John Thiruvadigal ^c and V. Manivannan ^d ^*

^aDepartment of Physics, Panimalar Institute of Technology, Chennai 600 095, India, ^bDepartment of Chemistry, SRM University, Ramapuram, Chennai 600 089, India, ^cDepartment of Physics, SRM University, Kattankulathur Campus, Chennai 603 203, India, and ^dDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 24 October 2008; accepted 31 October 2008; online 8 November 2008)

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 ); Yachi et al. (1989 ). For related structures, see: Manivannan et al. (2005 ); Ramachandran et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₂O₃S
M_r = 284.32
Orthorhombic, P 2₁ 2₁ 2₁
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 ) 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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.106
S = 1.01
5093 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.31 e Å⁻³
Absolute structure: Flack (1983 ), 1993 Friedel pairs
Flack parameter: −0.03 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.93	2.51	3.424 (2)	169
C5—H5⋯Cg2ⁱⁱ	0.93	2.96	3.486 (2)	117
C6—H6⋯Cg3ⁱⁱ	0.93	2.94	3.535 (2)	123
C12—H12⋯Cg1ⁱⁱⁱ	0.93	2.94	3.788 (3)	152
Symmetry codes: (i) x+1, y, z; (ii) $[-x+{\script{3\over 2}}, -y+2, z+{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{5\over 2}}, -z+{\script{1\over 2}}]$ . 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.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT; 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.

Supporting information

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

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

checkCIF report

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.

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

	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.

Phenyl naphthalene-2-sulfonate top

Crystal data top

C₁₆H₁₂O₃S	F(000) = 592
M_r = 284.32	D_x = 1.389 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4818 reflections
a = 6.1525 (2) Å	θ = 2.2–25.4°
b = 12.7466 (7) Å	µ = 0.24 mm⁻¹
c = 17.3414 (10) Å	T = 295 K
V = 1359.97 (12) Å³	Tablet, colourless
Z = 4	0.25 × 0.18 × 0.16 mm

Data collection top

Bruker Kappa APEXII diffractometer	5093 independent reflections
Radiation source: fine-focus sealed tube	3412 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 34.9°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→5
T_min = 0.942, T_max = 0.962	k = −19→18
11868 measured reflections	l = −25→27

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0476P)² + 0.0596P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
5093 reflections	Δρ_max = 0.26 e Å⁻³
181 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1993 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (7)

Crystal data top

C₁₆H₁₂O₃S	V = 1359.97 (12) Å³
M_r = 284.32	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.1525 (2) Å	µ = 0.24 mm⁻¹
b = 12.7466 (7) Å	T = 295 K
c = 17.3414 (10) Å	0.25 × 0.18 × 0.16 mm

Data collection top

Bruker Kappa APEXII diffractometer	5093 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3412 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.962	R_int = 0.027
11868 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.106	Δρ_max = 0.26 e Å⁻³
S = 1.01	Δρ_min = −0.31 e Å⁻³
5093 reflections	Absolute structure: Flack (1983), 1993 Friedel pairs
181 parameters	Absolute structure parameter: −0.03 (7)
0 restraints

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

	x	y	z	U_iso*/U_eq
S1	0.68361 (7)	0.89579 (3)	0.10630 (3)	0.03997 (11)
O1	0.8255 (2)	0.88973 (9)	0.18279 (6)	0.0403 (3)
O2	0.4945 (2)	0.95689 (12)	0.12058 (8)	0.0527 (4)
O3	0.6661 (3)	0.78918 (10)	0.08397 (9)	0.0646 (4)
C1	0.8523 (3)	0.98154 (12)	0.22766 (9)	0.0332 (3)
C2	1.0472 (3)	1.03331 (16)	0.22378 (11)	0.0438 (4)
H2	1.1557	1.0114	0.1901	0.053*
C3	1.0781 (3)	1.11934 (17)	0.27152 (13)	0.0537 (5)
H3	1.2089	1.1558	0.2701	0.064*
C4	0.9168 (3)	1.15065 (16)	0.32060 (12)	0.0513 (5)
H4	0.9389	1.2084	0.3524	0.062*
C5	0.7234 (3)	1.09789 (16)	0.32342 (10)	0.0497 (5)
H5	0.6144	1.1203	0.3567	0.060*
C6	0.6895 (3)	1.01146 (14)	0.27702 (10)	0.0422 (4)
H6	0.5594	0.9744	0.2792	0.051*
C7	0.8516 (3)	0.96307 (12)	0.04171 (9)	0.0334 (3)
C8	0.7855 (3)	1.05729 (12)	0.01241 (9)	0.0355 (4)
H8	0.6522	1.0855	0.0269	0.043*
C9	0.9203 (3)	1.11168 (13)	−0.03991 (10)	0.0380 (4)
C10	0.8568 (4)	1.20865 (14)	−0.07297 (12)	0.0522 (5)
H10	0.7231	1.2379	−0.0601	0.063*
C11	0.9892 (5)	1.25888 (17)	−0.12299 (12)	0.0652 (6)
H11	0.9458	1.3223	−0.1446	0.078*
C12	1.1911 (5)	1.2161 (2)	−0.14254 (12)	0.0709 (7)
H12	1.2808	1.2516	−0.1769	0.085*
C13	1.2580 (3)	1.12340 (18)	−0.11191 (12)	0.0569 (5)
H13	1.3933	1.0963	−0.1251	0.068*
C14	1.1230 (3)	1.06801 (14)	−0.06014 (10)	0.0405 (4)
C15	1.1837 (3)	0.96940 (15)	−0.02884 (10)	0.0439 (4)
H15	1.3164	0.9399	−0.0425	0.053*
C16	1.0520 (3)	0.91760 (13)	0.02050 (10)	0.0395 (4)
H16	1.0929	0.8527	0.0403	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0443 (2)	0.0406 (2)	0.0350 (2)	−0.00821 (18)	0.00007 (19)	−0.00279 (17)
O1	0.0525 (7)	0.0344 (5)	0.0339 (6)	0.0047 (6)	−0.0012 (5)	0.0021 (5)
O2	0.0361 (7)	0.0768 (9)	0.0451 (8)	−0.0027 (6)	0.0010 (6)	0.0017 (7)
O3	0.0897 (11)	0.0457 (7)	0.0584 (9)	−0.0245 (7)	0.0029 (9)	−0.0083 (6)
C1	0.0381 (10)	0.0353 (7)	0.0262 (7)	0.0012 (6)	−0.0017 (6)	0.0046 (6)
C2	0.0352 (10)	0.0579 (11)	0.0382 (9)	0.0016 (8)	0.0018 (7)	−0.0005 (8)
C3	0.0463 (12)	0.0649 (13)	0.0498 (12)	−0.0151 (10)	−0.0042 (9)	−0.0019 (10)
C4	0.0665 (14)	0.0508 (11)	0.0365 (11)	−0.0090 (9)	−0.0024 (9)	−0.0056 (8)
C5	0.0563 (13)	0.0562 (11)	0.0366 (9)	−0.0022 (9)	0.0132 (8)	−0.0060 (9)
C6	0.0413 (10)	0.0503 (9)	0.0348 (8)	−0.0094 (8)	0.0053 (8)	0.0016 (7)
C7	0.0373 (9)	0.0340 (7)	0.0290 (7)	−0.0004 (6)	−0.0011 (6)	−0.0049 (6)
C8	0.0374 (9)	0.0343 (7)	0.0348 (8)	0.0011 (7)	−0.0017 (7)	−0.0063 (6)
C9	0.0478 (10)	0.0338 (8)	0.0325 (8)	−0.0053 (7)	−0.0064 (7)	−0.0034 (7)
C10	0.0675 (14)	0.0375 (9)	0.0516 (11)	−0.0044 (8)	−0.0138 (10)	0.0012 (8)
C11	0.0953 (18)	0.0482 (11)	0.0521 (14)	−0.0225 (12)	−0.0208 (13)	0.0102 (9)
C12	0.0927 (18)	0.0760 (15)	0.0440 (12)	−0.0440 (15)	−0.0050 (13)	0.0084 (11)
C13	0.0562 (12)	0.0748 (13)	0.0396 (10)	−0.0233 (10)	0.0020 (8)	−0.0062 (10)
C14	0.0419 (11)	0.0515 (10)	0.0280 (8)	−0.0102 (8)	−0.0035 (7)	−0.0074 (7)
C15	0.0378 (10)	0.0594 (10)	0.0347 (9)	0.0062 (9)	−0.0008 (8)	−0.0070 (8)
C16	0.0451 (10)	0.0425 (9)	0.0310 (9)	0.0101 (7)	−0.0023 (7)	−0.0024 (7)

Geometric parameters (Å, º) top

S1—O3	1.4172 (13)	C7—C16	1.411 (2)
S1—O2	1.4217 (15)	C8—C9	1.411 (2)
S1—O1	1.5899 (13)	C8—H8	0.9300
S1—C7	1.7487 (17)	C9—C14	1.410 (3)
O1—C1	1.4149 (19)	C9—C10	1.417 (2)
C1—C2	1.370 (2)	C10—C11	1.351 (3)
C1—C6	1.372 (2)	C10—H10	0.9300
C2—C3	1.387 (3)	C11—C12	1.398 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.367 (3)	C12—C13	1.360 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.368 (3)	C13—C14	1.412 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.380 (3)	C14—C15	1.419 (3)
C5—H5	0.9300	C15—C16	1.351 (3)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.366 (2)	C16—H16	0.9300

O3—S1—O2	120.72 (10)	C7—C8—C9	119.74 (16)
O3—S1—O1	102.89 (9)	C7—C8—H8	120.1
O2—S1—O1	109.31 (7)	C9—C8—H8	120.1
O3—S1—C7	109.88 (9)	C14—C9—C8	119.07 (16)
O2—S1—C7	109.05 (8)	C14—C9—C10	119.18 (18)
O1—S1—C7	103.52 (7)	C8—C9—C10	121.74 (17)
C1—O1—S1	118.86 (10)	C11—C10—C9	120.4 (2)
C2—C1—C6	122.41 (16)	C11—C10—H10	119.8
C2—C1—O1	118.25 (15)	C9—C10—H10	119.8
C6—C1—O1	119.20 (15)	C10—C11—C12	120.4 (2)
C1—C2—C3	118.10 (17)	C10—C11—H11	119.8
C1—C2—H2	121.0	C12—C11—H11	119.8
C3—C2—H2	121.0	C13—C12—C11	120.9 (2)
C4—C3—C2	120.22 (18)	C13—C12—H12	119.6
C4—C3—H3	119.9	C11—C12—H12	119.6
C2—C3—H3	119.9	C12—C13—C14	120.3 (2)
C3—C4—C5	120.68 (18)	C12—C13—H13	119.8
C3—C4—H4	119.7	C14—C13—H13	119.8
C5—C4—H4	119.7	C9—C14—C13	118.75 (19)
C4—C5—C6	120.22 (17)	C9—C14—C15	119.15 (17)
C4—C5—H5	119.9	C13—C14—C15	122.09 (19)
C6—C5—H5	119.9	C16—C15—C14	121.17 (18)
C1—C6—C5	118.37 (17)	C16—C15—H15	119.4
C1—C6—H6	120.8	C14—C15—H15	119.4
C5—C6—H6	120.8	C15—C16—C7	119.23 (16)
C8—C7—C16	121.62 (16)	C15—C16—H16	120.4
C8—C7—S1	119.58 (13)	C7—C16—H16	120.4
C16—C7—S1	118.80 (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—C1	73.97 (13)	C7—C8—C9—C10	178.76 (16)
S1—O1—C1—C2	−104.08 (16)	C14—C9—C10—C11	−0.3 (3)
S1—O1—C1—C6	80.26 (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—C13	0.2 (3)
C1—C2—C3—C4	−0.1 (3)	C11—C12—C13—C14	0.6 (3)
C2—C3—C4—C5	0.0 (3)	C8—C9—C14—C13	−179.35 (16)
C3—C4—C5—C6	0.6 (3)	C10—C9—C14—C13	1.0 (2)
C2—C1—C6—C5	1.0 (3)	C8—C9—C14—C15	1.5 (2)
O1—C1—C6—C5	176.47 (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—C8	132.35 (14)	C12—C13—C14—C15	177.93 (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—C16	178.67 (12)	C8—C7—C16—C15	1.3 (2)
O1—S1—C7—C16	62.39 (13)	S1—C7—C16—C15	−179.43 (14)
C16—C7—C8—C9	−0.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.51	3.424 (2)	169
C5—H5···Cg2ⁱⁱ	0.93	2.96	3.486 (2)	117
C6—H6···Cg3ⁱⁱ	0.93	2.94	3.535 (2)	123
C12—H12···Cg1ⁱⁱⁱ	0.93	2.94	3.788 (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.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂O₃S
M_r	284.32
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	6.1525 (2), 12.7466 (7), 17.3414 (10)
V (Å³)	1359.97 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.25 × 0.18 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.942, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	11868, 5093, 3412
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.805

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.106, 1.01
No. of reflections	5093
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.31
Absolute structure	Flack (1983), 1993 Friedel pairs
Absolute structure parameter	−0.03 (7)

Computer programs: , APEX2 (Bruker, 2004) and SAINT (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.51	3.424 (2)	169
C5—H5···Cg2ⁱⁱ	0.93	2.96	3.486 (2)	117
C6—H6···Cg3ⁱⁱ	0.93	2.94	3.535 (2)	123
C12—H12···Cg1ⁱⁱⁱ	0.93	2.94	3.788 (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

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

References

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