Phenyl naphthalene-2-sulfonate.

In the crystal structure of the title compound, C(16)H(12)O(3)S, the dihedral angle between the naphthalene ring system and the phenyl ring is 65.21 (3)°. The mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds, forming a chain along the a axis. The chains are connected through weak C-H⋯π inter-actions.

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 = 284.32

Orthorhombic,

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 (; 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[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 ▶), 1993 Friedel pairs

Flack parameter: −0.03 (7)

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.

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

C16H12O3S	F000 = 592
Mr = 284.32	Dx = 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 = 2.2–25.4º
b = 12.7466 (7) Å	µ = 0.24 mm−1
c = 17.3414 (10) Å	T = 295 (2) K
V = 1359.97 (12) Å3	Tablet, colourless
Z = 4	0.25 × 0.18 × 0.16 mm

Bruker Kappa APEXII diffractometer	5093 independent reflections
Radiation source: fine-focus sealed tube	3412 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
T = 295(2) K	θmax = 34.9º
ω and φ scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→5
Tmin = 0.942, Tmax = 0.962	k = −19→18
11868 measured reflections	l = −25→27

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-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 = 1.01	Δρmax = 0.26 e Å−3
5093 reflections	Δρmin = −0.31 e Å−3
181 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1993 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.03 (7)

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) . 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.