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Acta Cryst. (2009). E65, o72    [ doi:10.1107/S1600536808041032 ]

3-Aminophenyl naphthalene-1-sulfonate

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

Abstract top

In the title compound, C16H13NO3S, the plane of the naphthalene ring system forms a dihedral angle of 64.66 (10)° with the benzene ring. The molecular structure is stabilized by weak intramolecular C-H...O interactions and the crystal packing is stabilized by weak intermolecular N-H...O and C-H...O interactions and by [pi]-[pi] stacking interactions of the inversion-related naphthalene units [centroid-centroid distance of 3.7373 (14) Å].

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 plane of the benzene ring forms a dihedral angle of 64.66 (10) ° with the naphthalene ring system. The torsion angles O2—S1—C1—C2 and O3—S1—C1—C10 [5.58 (17) ° and 52.09 (16) °, respectively] indicate the syn conformation of sulfonyl moiety. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular C—H···O interactions, N—H···O interactions and π-π stacking interactions of the naphthalene fragments related by inversion center

Related literature top

For the structures of closely related compounds, see: Manivannan et al. (2005a,b); Ramachandran et al.(2007); Vennila et al. (2008). For applications, see: Spungin et al. (1984); Yachi et al. (1989).

Experimental top

1-Napthalene sulfonyl chloride (5 mmol) dissolved in acetone (4 ml) was added dropwise to 3-amino phenol (5 mmol) in aqueous NaOH (4 ml, 5%) with constant shaking. The precipitated compound (3 mmol, yield 60%) was recrystlized from ethanol to get diffraction quality brown colored 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) for aromatic C—H and N—H = 0.86 Å and Uiso(H) = 1.2Ueq(N) for N—H.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: 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 the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
3-Aminophenyl naphthalene-1-sulfonate top
Crystal data top
C16H13NO3SF(000) = 624
Mr = 299.33Dx = 1.407 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4818 reflections
a = 8.4558 (2) Åθ = 2.2–25.4°
b = 8.6712 (3) ŵ = 0.24 mm−1
c = 19.5915 (6) ÅT = 295 K
β = 100.321 (2)°Block, brown
V = 1413.24 (7) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker Kappa APEX2
diffractometer		4981 independent reflections
Radiation source: fine-focus sealed tube3126 reflections with I > 2σ(I)
graphiteRint = 0.023
ω and φ scansθmax = 32.2°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→10
Tmin = 0.932, Tmax = 0.954k = −12→11
19808 measured reflectionsl = −21→29
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0763P)2 + 0.3485P]
where P = (Fo2 + 2Fc2)/3
4981 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.46 e Å−3
0 restraintsΔρmin = −0.44 e Å−3
Crystal data top
C16H13NO3SV = 1413.24 (7) Å3
Mr = 299.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.4558 (2) ŵ = 0.24 mm−1
b = 8.6712 (3) ÅT = 295 K
c = 19.5915 (6) Å0.30 × 0.25 × 0.20 mm
β = 100.321 (2)°
Data collection top
Bruker Kappa APEX2
diffractometer		3126 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.023
Tmin = 0.932, Tmax = 0.954θmax = 32.2°
19808 measured reflectionsStandard reflections: 0
4981 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.174Δρmax = 0.46 e Å−3
S = 1.05Δρmin = −0.44 e Å−3
4981 reflectionsAbsolute structure: ?
190 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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
xyzUiso*/Ueq
C10.34222 (19)0.8581 (2)0.10826 (8)0.0475 (4)
C20.2573 (3)0.9698 (3)0.13547 (12)0.0688 (6)
H20.25430.97010.18270.083*
C30.1749 (3)1.0837 (3)0.09239 (19)0.0876 (8)
H30.11731.15960.11090.105*
C40.1793 (3)1.0828 (3)0.02504 (18)0.0858 (8)
H40.12411.1593−0.00290.103*
C50.2639 (2)0.9713 (2)−0.00569 (11)0.0634 (5)
C60.2687 (4)0.9715 (4)−0.07762 (13)0.0910 (9)
H60.21221.0468−0.10580.109*
C70.3515 (4)0.8673 (4)−0.10559 (13)0.1015 (12)
H70.35370.8711−0.15290.122*
C80.4342 (4)0.7536 (3)−0.06564 (14)0.0872 (9)
H80.49130.6808−0.08630.105*
C90.4342 (2)0.7451 (2)0.00414 (11)0.0619 (5)
H90.49040.66660.03030.074*
C100.34948 (19)0.85482 (19)0.03643 (8)0.0458 (4)
C110.21070 (19)0.52112 (19)0.14424 (9)0.0466 (4)
C120.0822 (2)0.5617 (2)0.09445 (10)0.0595 (5)
H120.09490.61760.05530.071*
C13−0.0674 (2)0.5150 (3)0.10555 (12)0.0696 (6)
H13−0.15820.54140.07340.084*
C14−0.0850 (2)0.4309 (2)0.16279 (11)0.0637 (5)
H14−0.18740.40250.16920.076*
C150.0471 (2)0.3876 (2)0.21112 (10)0.0561 (4)
C160.1979 (2)0.4357 (2)0.20153 (9)0.0511 (4)
H160.28900.41010.23360.061*
O10.36734 (15)0.56180 (15)0.13433 (7)0.0580 (3)
O20.3993 (2)0.7447 (2)0.23185 (7)0.0915 (6)
O30.60456 (18)0.7106 (2)0.15880 (10)0.0903 (6)
N10.0316 (3)0.3014 (3)0.26868 (11)0.0868 (6)
H1A−0.06210.27330.27520.104*
H1B0.11560.27580.29810.104*
S10.44040 (6)0.72128 (7)0.16539 (2)0.06166 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0464 (8)0.0490 (9)0.0497 (8)−0.0131 (7)0.0153 (6)−0.0086 (7)
C20.0679 (12)0.0677 (13)0.0789 (13)−0.0188 (10)0.0346 (10)−0.0268 (11)
C30.0697 (14)0.0536 (13)0.144 (3)0.0011 (10)0.0312 (15)−0.0233 (15)
C40.0699 (14)0.0511 (12)0.130 (2)−0.0040 (10)0.0007 (14)0.0086 (14)
C50.0621 (11)0.0556 (11)0.0683 (12)−0.0236 (9)0.0003 (9)0.0073 (9)
C60.1060 (19)0.0930 (19)0.0634 (13)−0.0531 (16)−0.0135 (13)0.0241 (13)
C70.136 (3)0.118 (2)0.0525 (13)−0.082 (2)0.0230 (15)−0.0135 (15)
C80.1037 (19)0.0958 (19)0.0737 (14)−0.0525 (16)0.0469 (14)−0.0426 (14)
C90.0619 (11)0.0660 (12)0.0638 (11)−0.0206 (9)0.0276 (9)−0.0226 (9)
C100.0451 (8)0.0451 (8)0.0482 (8)−0.0160 (6)0.0112 (6)−0.0062 (6)
C110.0461 (8)0.0416 (8)0.0523 (9)−0.0039 (6)0.0095 (6)−0.0014 (7)
C120.0603 (10)0.0606 (11)0.0536 (10)−0.0068 (9)−0.0006 (8)0.0050 (8)
C130.0519 (10)0.0769 (14)0.0725 (13)−0.0074 (9)−0.0091 (9)−0.0047 (11)
C140.0522 (10)0.0598 (11)0.0798 (13)−0.0175 (8)0.0139 (9)−0.0150 (10)
C150.0643 (10)0.0438 (9)0.0640 (11)−0.0099 (8)0.0214 (9)−0.0058 (8)
C160.0524 (9)0.0452 (9)0.0546 (9)−0.0002 (7)0.0068 (7)0.0035 (7)
O10.0501 (6)0.0556 (7)0.0704 (8)−0.0023 (5)0.0165 (6)0.0074 (6)
O20.1164 (14)0.1138 (14)0.0419 (7)−0.0494 (11)0.0078 (8)−0.0014 (8)
O30.0456 (8)0.1086 (14)0.1099 (14)−0.0144 (8)−0.0046 (8)0.0307 (11)
N10.0905 (14)0.0891 (15)0.0865 (14)−0.0159 (11)0.0316 (11)0.0238 (11)
S10.0536 (3)0.0762 (4)0.0524 (3)−0.0199 (2)0.00177 (19)0.0072 (2)
Geometric parameters (Å, °) top
C1—C21.370 (3)C9—H90.9300
C1—C101.420 (2)C11—C161.365 (2)
C1—S11.7368 (19)C11—C121.370 (2)
C2—C31.401 (4)C11—O11.4173 (19)
C2—H20.9300C12—C131.382 (3)
C3—C41.327 (4)C12—H120.9300
C3—H30.9300C13—C141.368 (3)
C4—C51.401 (4)C13—H130.9300
C4—H40.9300C14—C151.381 (3)
C5—C61.417 (3)C14—H140.9300
C5—C101.418 (3)C15—N11.378 (3)
C6—C71.321 (5)C15—C161.386 (2)
C6—H60.9300C16—H160.9300
C7—C81.370 (5)O1—S11.5905 (14)
C7—H70.9300O2—S11.4212 (16)
C8—C91.369 (3)O3—S11.4199 (16)
C8—H80.9300N1—H1A0.8600
C9—C101.408 (3)N1—H1B0.8600
C2—C1—C10121.24 (18)C5—C10—C1117.02 (17)
C2—C1—S1117.12 (15)C16—C11—C12123.72 (16)
C10—C1—S1121.63 (13)C16—C11—O1117.47 (15)
C1—C2—C3120.2 (2)C12—C11—O1118.71 (16)
C1—C2—H2119.9C11—C12—C13116.40 (18)
C3—C2—H2119.9C11—C12—H12121.8
C4—C3—C2119.7 (2)C13—C12—H12121.8
C4—C3—H3120.2C14—C13—C12121.48 (18)
C2—C3—H3120.2C14—C13—H13119.3
C3—C4—C5122.6 (2)C12—C13—H13119.3
C3—C4—H4118.7C13—C14—C15120.92 (18)
C5—C4—H4118.7C13—C14—H14119.5
C4—C5—C6122.3 (3)C15—C14—H14119.5
C4—C5—C10119.2 (2)N1—C15—C14121.64 (19)
C6—C5—C10118.5 (2)N1—C15—C16119.91 (19)
C7—C6—C5121.6 (3)C14—C15—C16118.43 (17)
C7—C6—H6119.2C11—C16—C15119.01 (16)
C5—C6—H6119.2C11—C16—H16120.5
C6—C7—C8120.6 (2)C15—C16—H16120.5
C6—C7—H7119.7C11—O1—S1118.20 (11)
C8—C7—H7119.7C15—N1—H1A120.0
C9—C8—C7121.2 (3)C15—N1—H1B120.0
C9—C8—H8119.4H1A—N1—H1B120.0
C7—C8—H8119.4O3—S1—O2119.75 (11)
C8—C9—C10120.2 (2)O3—S1—O1103.16 (10)
C8—C9—H9119.9O2—S1—O1109.45 (9)
C10—C9—H9119.9O3—S1—C1110.36 (9)
C9—C10—C5117.90 (18)O2—S1—C1108.99 (11)
C9—C10—C1125.09 (18)O1—S1—C1103.85 (7)
C10—C1—C2—C30.2 (3)C16—C11—C12—C131.8 (3)
S1—C1—C2—C3−179.87 (16)O1—C11—C12—C13178.00 (17)
C1—C2—C3—C40.1 (3)C11—C12—C13—C14−0.9 (3)
C2—C3—C4—C50.1 (4)C12—C13—C14—C15−1.0 (3)
C3—C4—C5—C6−179.7 (2)C13—C14—C15—N1−179.3 (2)
C3—C4—C5—C10−0.5 (3)C13—C14—C15—C162.1 (3)
C4—C5—C6—C7178.7 (2)C12—C11—C16—C15−0.7 (3)
C10—C5—C6—C7−0.6 (3)O1—C11—C16—C15−176.96 (15)
C5—C6—C7—C80.9 (4)N1—C15—C16—C11−179.90 (18)
C6—C7—C8—C9−0.4 (4)C14—C15—C16—C11−1.3 (3)
C7—C8—C9—C10−0.5 (3)C16—C11—O1—S1−91.61 (17)
C8—C9—C10—C50.8 (3)C12—C11—O1—S191.97 (18)
C8—C9—C10—C1−179.44 (16)C11—O1—S1—O3168.69 (12)
C4—C5—C10—C9−179.52 (17)C11—O1—S1—O240.15 (16)
C6—C5—C10—C9−0.3 (2)C11—O1—S1—C1−76.12 (13)
C4—C5—C10—C10.7 (2)C2—C1—S1—O3−127.86 (16)
C6—C5—C10—C1179.93 (16)C10—C1—S1—O352.09 (16)
C2—C1—C10—C9179.68 (17)C2—C1—S1—O25.58 (17)
S1—C1—C10—C9−0.3 (2)C10—C1—S1—O2−174.48 (13)
C2—C1—C10—C5−0.6 (2)C2—C1—S1—O1122.16 (14)
S1—C1—C10—C5179.50 (12)C10—C1—S1—O1−57.89 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O20.932.412.829 (3)107
C9—H9···O30.932.563.127 (3)120
N1—H1B···O3i0.862.433.246 (3)158
C7—H7···O2ii0.932.563.422 (3)154
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+3/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O20.932.412.829 (3)107
C9—H9···O30.932.563.127 (3)120
N1—H1B···O3i0.862.433.246 (3)158
C7—H7···O2ii0.932.563.422 (3)154
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+3/2, 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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