2-Naphthyl benzene­sulfonate

Vembu, N.; Shafna, K.C.; Sparkes, H.A.; Howard, J.A.K.

doi:10.1107/S160053680703437X

2-Naphthyl benzenesulfonate

N. Vembu, K. C. Shafna, H. A. Sparkes and J. A. K. Howard

The phenyl and naphthyl ring systems are at an angle of 47.57 (9)° in the title compound, C₁₆H₁₂O₃S. Only weak C—H

O interactions are present in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703437X/gg2026sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680703437X/gg2026Isup2.hkl Contains datablock I

CCDC reference: 659092

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Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R factor = 0.047
wR factor = 0.127
Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.814     1.000
            Tmin(prime) and Tmax expected:      0.943     0.981
            RR(prime) =      0.847
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.85
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Aromatic sulfonates are used in monitoring the merging of lipids (Yachi et al., 1989) and in many other fields (Spungin et al., 1992, Tharakan et al.,1992, Alford et al., 1991, Jiang et al., 1990, Narayanan & Krakow, 1983). An X-ray study of the title compound (I) was undertaken in order to determine its crystal and molecular structure owing to the biological importance of its analogues. The molecular structure of (I) is shown in Fig. 1 with selected geometric parameters provided in Table 1. The S—C, S—O and S=O bond lengths are comparable with those found in related structures previously reported by our research group (Manivannan et al. 2005 & references cited therein).

A Newman projection along the O10—S1 bond is provided in Fig. 2. Using C11 as a reference point, the orientations of the two sulfonyl oxygen atoms (O8 and O9) and the phenyl carbon (C2) have been deduced from the corresponding torsion angles (C11–O10–S1–O8/O9/C2). Helical nomeclature is employed to assign + or -synclinal and +antiperiplanar conformations. The C2–S1–O10–C11 torsion angle of 60.6 (2)° corresponds to +synclinal conformation; as expected the dihedral angle between the mean planes of the phenyl and naphthyl rings of 47.57 (7)° shows that the two rings are not coplanar. This is similar to the situation reported by us for other aromatic sulfonates (Manivannan et al. 2005 & references cited therein).

The crystal structure of (I) is stabilized by weak intermolecular C—H···O interactions (Desiraju et al., 1999) (Table 2, Fig. 3).

Related literature top

For a detailed account of the molecular and supramolecular architectures of aromatic sulfonates, see Manivannan et al. (2005) and references cited therein.

For related literature, see: Alford et al. (1991); Desiraju & Steiner (1999); Jiang et al. (1990); Narayanan & Krakow (1983); Sheldrick (1998b); Spungin et al. (1992); Tharakan et al. (1992).

Experimental top

Benzenesulfonyl chloride (10 mmol), dissolved in acetone, was added dropwise to 2-naphthol (10 mmol) in aqueous NaOH (8 ml, 5%) with constant stirring. The precipitate (6.5 mmol, yield 65%) was filtered and recrystallized from aqueous ethanol.

Structure description top

The crystal structure of (I) is stabilized by weak intermolecular C—H···O interactions (Desiraju et al., 1999) (Table 2, Fig. 3).

For a detailed account of the molecular and supramolecular architectures of aromatic sulfonates, see Manivannan et al. (2005) and references cited therein.

For related literature, see: Alford et al. (1991); Desiraju & Steiner (1999); Jiang et al. (1990); Narayanan & Krakow (1983); Sheldrick (1998b); Spungin et al. (1992); Tharakan et al. (1992).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The asymmetric unit of (I) with the atoms labelled and displacement ellipsoids depicted at the 50% probability level for all non-H atoms. H-atoms are drawn as spheres of arbitrary radius
	Fig. 2. A Newman projection along the O10—S1 bond with C11 as a reference point, +/-sc = +/-synclinal, -ap = -antiperiplanar.
	Fig. 3. The molecular packing viewed down the b-axis. Dashed lines represent the weak C—H···O interactions within the lattice.

2-Napthyl benzenesulfonate top

Crystal data top

C₁₆H₁₂O₃S	D_x = 1.392 Mg m⁻³
M_r = 284.32	Melting point = 394–396 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2747 reflections
a = 11.8910 (11) Å	θ = 2.5–27.3°
b = 10.8909 (12) Å	µ = 0.24 mm⁻¹
c = 20.958 (2) Å	T = 120 K
V = 2714.1 (5) Å³	Plate, colourless
Z = 8	0.24 × 0.16 × 0.08 mm
F(000) = 1184

Data collection top

Bruker SMART CCD 1K area-detector diffractometer	3917 independent reflections
Radiation source: fine-focus sealed tube	2262 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.089
Detector resolution: 8 pixels mm^-1	θ_max = 30.4°, θ_min = 1.9°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1998a)	k = −15→14
T_min = 0.814, T_max = 1.000	l = −29→21
19056 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	All H-atom parameters refined
S = 1.00	w = 1/[σ²(F_o²) + (0.0529P)² + 0.8434P] where P = (F_o² + 2F_c²)/3
3917 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₆H₁₂O₃S	V = 2714.1 (5) Å³
M_r = 284.32	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 11.8910 (11) Å	µ = 0.24 mm⁻¹
b = 10.8909 (12) Å	T = 120 K
c = 20.958 (2) Å	0.24 × 0.16 × 0.08 mm

Data collection top

Bruker SMART CCD 1K area-detector diffractometer	3917 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998a)	2262 reflections with I > 2σ(I)
T_min = 0.814, T_max = 1.000	R_int = 0.089
19056 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.127	All H-atom parameters refined
S = 1.00	Δρ_max = 0.33 e Å⁻³
3917 reflections	Δρ_min = −0.46 e Å⁻³
229 parameters

Special details top

Experimental. none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
S1	0.15762 (4)	0.88595 (5)	0.40500 (2)	0.01934 (14)
C2	0.30301 (18)	0.8898 (2)	0.39181 (10)	0.0187 (4)
C3	0.3510 (2)	0.8047 (2)	0.35098 (11)	0.0250 (5)
C4	0.4658 (2)	0.8075 (2)	0.34121 (12)	0.0315 (6)
C5	0.5312 (2)	0.8953 (2)	0.37184 (12)	0.0313 (6)
C6	0.4828 (2)	0.9788 (2)	0.41258 (13)	0.0308 (6)
C7	0.36756 (19)	0.9777 (2)	0.42299 (11)	0.0248 (5)
O8	0.10154 (13)	0.83470 (15)	0.35111 (7)	0.0274 (4)
O9	0.12184 (13)	1.00159 (14)	0.42973 (7)	0.0255 (4)
O10	0.14112 (12)	0.78362 (13)	0.45886 (7)	0.0206 (3)
C11	0.19407 (19)	0.8014 (2)	0.51926 (10)	0.0188 (5)
C12	0.29256 (19)	0.7343 (2)	0.53019 (11)	0.0216 (5)
C13	0.3430 (2)	0.7432 (2)	0.58838 (11)	0.0227 (5)
C14	0.3508 (2)	0.8323 (2)	0.69741 (11)	0.0261 (5)
C15	0.3072 (2)	0.9087 (2)	0.74265 (12)	0.0311 (6)
C16	0.2074 (2)	0.9743 (2)	0.73036 (12)	0.0319 (6)
C17	0.1535 (2)	0.9632 (2)	0.67294 (11)	0.0270 (5)
C18	0.14591 (19)	0.8753 (2)	0.56366 (10)	0.0200 (5)
C19	0.29784 (19)	0.8194 (2)	0.63705 (11)	0.0207 (5)
C20	0.19838 (19)	0.8870 (2)	0.62448 (10)	0.0201 (5)
H3	0.306 (2)	0.745 (2)	0.3302 (11)	0.024 (6)*
H4	0.503 (2)	0.749 (2)	0.3146 (11)	0.030 (7)*
H5	0.610 (2)	0.894 (2)	0.3643 (11)	0.028 (6)*
H6	0.523 (2)	1.039 (2)	0.4320 (12)	0.041 (8)*
H7	0.3328 (19)	1.037 (2)	0.4526 (12)	0.030 (7)*
H12	0.3242 (19)	0.686 (2)	0.4979 (11)	0.020 (6)*
H13	0.412 (2)	0.695 (2)	0.5964 (11)	0.025 (6)*
H14	0.420 (2)	0.787 (2)	0.7050 (11)	0.030 (7)*
H15	0.343 (2)	0.916 (2)	0.7828 (13)	0.038 (7)*
H16	0.182 (2)	1.024 (3)	0.7619 (15)	0.051 (9)*
H17	0.081 (2)	1.005 (2)	0.6640 (10)	0.022 (6)*
H18	0.076 (2)	0.918 (2)	0.5537 (10)	0.019 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0171 (2)	0.0239 (3)	0.0170 (3)	−0.0006 (2)	−0.0006 (2)	0.0004 (2)
C2	0.0173 (10)	0.0218 (11)	0.0172 (10)	−0.0002 (9)	−0.0022 (8)	0.0032 (9)
C3	0.0253 (12)	0.0258 (13)	0.0241 (12)	0.0005 (11)	−0.0020 (10)	−0.0049 (9)
C4	0.0284 (13)	0.0372 (15)	0.0289 (13)	0.0110 (12)	0.0037 (11)	−0.0033 (11)
C5	0.0182 (11)	0.0428 (16)	0.0328 (14)	0.0026 (12)	0.0033 (11)	0.0128 (12)
C6	0.0238 (13)	0.0322 (14)	0.0365 (15)	−0.0080 (11)	−0.0007 (11)	0.0025 (12)
C7	0.0243 (12)	0.0227 (12)	0.0273 (12)	−0.0032 (10)	0.0030 (10)	−0.0013 (10)
O8	0.0240 (9)	0.0384 (10)	0.0199 (8)	−0.0049 (7)	−0.0037 (7)	−0.0012 (7)
O9	0.0245 (8)	0.0258 (9)	0.0262 (9)	0.0065 (7)	0.0022 (7)	0.0005 (7)
O10	0.0212 (8)	0.0238 (8)	0.0168 (7)	−0.0054 (6)	−0.0014 (6)	−0.0001 (6)
C11	0.0209 (10)	0.0197 (11)	0.0160 (10)	−0.0034 (9)	−0.0012 (9)	0.0012 (9)
C12	0.0242 (12)	0.0196 (11)	0.0211 (11)	0.0009 (9)	0.0033 (10)	−0.0004 (9)
C13	0.0202 (11)	0.0229 (11)	0.0248 (12)	0.0004 (10)	0.0008 (10)	0.0006 (9)
C14	0.0270 (12)	0.0286 (13)	0.0227 (12)	−0.0019 (11)	−0.0055 (11)	0.0040 (10)
C15	0.0410 (15)	0.0333 (14)	0.0191 (12)	−0.0080 (12)	−0.0065 (11)	0.0027 (10)
C16	0.0455 (16)	0.0301 (14)	0.0201 (12)	0.0013 (12)	0.0050 (12)	−0.0039 (11)
C17	0.0318 (13)	0.0277 (13)	0.0216 (12)	0.0044 (11)	0.0046 (11)	0.0014 (10)
C18	0.0183 (11)	0.0227 (11)	0.0188 (11)	0.0000 (10)	−0.0005 (9)	0.0038 (9)
C19	0.0215 (11)	0.0198 (11)	0.0210 (11)	−0.0038 (9)	−0.0004 (9)	0.0029 (9)
C20	0.0248 (11)	0.0178 (11)	0.0177 (10)	−0.0018 (10)	0.0005 (9)	0.0036 (9)

Geometric parameters (Å, º) top

S1—O8	1.4254 (16)	C11—C12	1.399 (3)
S1—O9	1.4267 (16)	C12—C13	1.363 (3)
S1—O10	1.5983 (15)	C12—H12	0.93 (2)
S1—C2	1.751 (2)	C13—C19	1.420 (3)
C2—C3	1.384 (3)	C13—H13	0.99 (2)
C2—C7	1.390 (3)	C14—C15	1.363 (4)
C3—C4	1.382 (3)	C14—C19	1.420 (3)
C3—H3	0.94 (2)	C14—H14	0.97 (3)
C4—C5	1.389 (4)	C15—C16	1.409 (4)
C4—H4	0.95 (2)	C15—H15	0.95 (3)
C5—C6	1.374 (4)	C16—C17	1.368 (3)
C5—H5	0.95 (3)	C16—H16	0.91 (3)
C6—C7	1.388 (3)	C17—C20	1.416 (3)
C6—H6	0.91 (3)	C17—H17	0.99 (2)
C7—H7	0.99 (2)	C18—C20	1.425 (3)
O10—C11	1.427 (2)	C18—H18	0.98 (2)
C11—C18	1.358 (3)	C19—C20	1.418 (3)

O8—S1—O9	119.60 (10)	C13—C12—C11	118.5 (2)
O8—S1—O10	103.24 (9)	C13—C12—H12	120.8 (14)
O9—S1—O10	108.81 (9)	C11—C12—H12	120.7 (14)
O8—S1—C2	110.25 (10)	C12—C13—C19	121.2 (2)
O9—S1—C2	109.31 (10)	C12—C13—H13	118.7 (13)
O10—S1—C2	104.43 (9)	C19—C13—H13	120.1 (13)
C3—C2—C7	121.6 (2)	C15—C14—C19	120.8 (2)
C3—C2—S1	119.23 (18)	C15—C14—H14	121.2 (14)
C7—C2—S1	119.16 (17)	C19—C14—H14	118.0 (14)
C4—C3—C2	119.0 (2)	C14—C15—C16	120.1 (2)
C4—C3—H3	120.2 (14)	C14—C15—H15	119.8 (16)
C2—C3—H3	120.8 (15)	C16—C15—H15	120.0 (16)
C3—C4—C5	120.0 (2)	C17—C16—C15	120.7 (2)
C3—C4—H4	121.9 (15)	C17—C16—H16	122.7 (19)
C5—C4—H4	118.1 (15)	C15—C16—H16	116.6 (19)
C6—C5—C4	120.6 (2)	C16—C17—C20	120.4 (2)
C6—C5—H5	121.7 (15)	C16—C17—H17	122.1 (13)
C4—C5—H5	117.7 (14)	C20—C17—H17	117.4 (13)
C5—C6—C7	120.3 (2)	C11—C18—C20	118.8 (2)
C5—C6—H6	122.2 (17)	C11—C18—H18	119.8 (13)
C7—C6—H6	117.4 (17)	C20—C18—H18	121.5 (13)
C6—C7—C2	118.5 (2)	C20—C19—C14	119.0 (2)
C6—C7—H7	120.4 (14)	C20—C19—C13	119.0 (2)
C2—C7—H7	121.0 (14)	C14—C19—C13	122.0 (2)
C11—O10—S1	118.55 (13)	C17—C20—C19	119.0 (2)
C18—C11—C12	123.4 (2)	C17—C20—C18	122.0 (2)
C18—C11—O10	120.15 (19)	C19—C20—C18	119.0 (2)
C12—C11—O10	116.35 (19)

O8—S1—C2—C3	−27.2 (2)	O10—C11—C12—C13	−176.67 (19)
O9—S1—C2—C3	−160.58 (17)	C11—C12—C13—C19	−0.5 (3)
O10—S1—C2—C3	83.12 (19)	C19—C14—C15—C16	1.2 (4)
O8—S1—C2—C7	153.28 (17)	C14—C15—C16—C17	−0.6 (4)
O9—S1—C2—C7	19.9 (2)	C15—C16—C17—C20	−1.0 (4)
O10—S1—C2—C7	−96.41 (19)	C12—C11—C18—C20	0.7 (3)
C7—C2—C3—C4	0.1 (4)	O10—C11—C18—C20	177.35 (18)
S1—C2—C3—C4	−179.43 (19)	C15—C14—C19—C20	−0.2 (3)
C2—C3—C4—C5	−0.4 (4)	C15—C14—C19—C13	178.2 (2)
C3—C4—C5—C6	0.8 (4)	C12—C13—C19—C20	0.0 (3)
C4—C5—C6—C7	−0.9 (4)	C12—C13—C19—C14	−178.4 (2)
C5—C6—C7—C2	0.5 (4)	C16—C17—C20—C19	2.0 (3)
C3—C2—C7—C6	−0.2 (3)	C16—C17—C20—C18	−178.6 (2)
S1—C2—C7—C6	179.36 (18)	C14—C19—C20—C17	−1.4 (3)
O8—S1—O10—C11	175.90 (15)	C13—C19—C20—C17	−179.8 (2)
O9—S1—O10—C11	−56.06 (17)	C14—C19—C20—C18	179.2 (2)
C2—S1—O10—C11	60.58 (17)	C13—C19—C20—C18	0.8 (3)
S1—O10—C11—C18	81.0 (2)	C11—C18—C20—C17	179.5 (2)
S1—O10—C11—C12	−102.1 (2)	C11—C18—C20—C19	−1.1 (3)
C18—C11—C12—C13	0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O9	0.99 (2)	2.58 (2)	2.937 (3)	101.1 (16)
C12—H12···O9ⁱ	0.93 (2)	2.55 (2)	3.448 (3)	161.6 (19)
C13—H13···O8ⁱⁱ	0.99 (2)	2.52 (2)	3.432 (3)	152.1 (18)
C18—H18···O9ⁱⁱⁱ	0.98 (2)	2.53 (2)	3.457 (3)	157.8 (17)
C5—H5···Cg2^iv	0.95 (3)	3.007	3.554	118.05
C5—H5···Cg3^v	0.95 (3)	2.977	3.617	125.99
C6—H6···Cg2^v	0.91 (3)	3.209	3.973	142.81
C15—H15···Cg1^vi	0.95 (3)	3.073	3.862	141.70

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂O₃S
M_r	284.32
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	120
a, b, c (Å)	11.8910 (11), 10.8909 (12), 20.958 (2)
V (Å³)	2714.1 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.24 × 0.16 × 0.08

Data collection
Diffractometer	Bruker SMART CCD 1K area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998a)
T_min, T_max	0.814, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	19056, 3917, 2262
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.713

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.127, 1.00
No. of reflections	3917
No. of parameters	229
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.46

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), SHELXL97.

Selected geometric parameters (Å, º) top

S1—O8	1.4254 (16)	S1—O10	1.5983 (15)
S1—O9	1.4267 (16)	S1—C2	1.751 (2)

O8—S1—O9	119.60 (10)	O9—S1—C2	109.31 (10)
O8—S1—O10	103.24 (9)	O10—S1—C2	104.43 (9)
O9—S1—O10	108.81 (9)	C11—O10—S1	118.55 (13)
O8—S1—C2	110.25 (10)

O8—S1—O10—C11	175.90 (15)	C2—S1—O10—C11	60.58 (17)
O9—S1—O10—C11	−56.06 (17)