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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o72.
Published online 2008 December 10. doi:  10.1107/S1600536808041032
PMCID: PMC2967982

3-Amino­phenyl naphthalene-1-sulfonate

Abstract

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 π–π stacking inter­actions of the inversion-related naphthalene units [centroid–centroid distance of 3.7373 (14) Å].

Related literature

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

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Object name is e-65-00o72-scheme1.jpg

Experimental

Crystal data

  • C16H13NO3S
  • M r = 299.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00o72-efi1.jpg
  • a = 8.4558 (2) Å
  • b = 8.6712 (3) Å
  • c = 19.5915 (6) Å
  • β = 100.321 (2)°
  • V = 1413.24 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 295 (2) K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.932, T max = 0.954
  • 19808 measured reflections
  • 4981 independent reflections
  • 3126 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.174
  • S = 1.05
  • 4981 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.46 e Å−3
  • Δρmin = −0.44 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041032/gk2179sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041032/gk2179Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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

Experimental

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

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.

Figures

Fig. 1.
The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
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.

Crystal data

C16H13NO3SF(000) = 624
Mr = 299.33Dx = 1.407 Mg m3
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 mm1
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

Bruker Kappa APEX2 diffractometer4981 independent reflections
Radiation source: fine-focus sealed tube3126 reflections with I > 2σ(I)
graphiteRint = 0.023
ω and [var phi] 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

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 = 1.05w = 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 Å3
0 restraintsΔρmin = −0.44 e Å3

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2179).

References

  • Bruker (2004). APEX2 andSAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Manivannan, V., Vembu, N., Nallu, M., Sivakumar, K. & Fronczek, F. R. (2005a). Acta Cryst. E61, o239–o241.
  • Manivannan, V., Vembu, N., Nallu, M., Sivakumar, K. & Fronczek, F. R. (2005b). Acta Cryst. E61, o242–o244.
  • Ramachandran, G., Kanakam, C. C., Manivannan, V., Thiruvenkatam, V. & Row, T. N. G. (2007). Acta Cryst. E63, o4638.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Spungin, B., Levinshal, T., Rubenstein, S. & Breitbart, H. (1984). Biochim. Biophys. Acta, 769, 531–542.
  • Vennila, J. P., Kavitha, H. P., Thiruvadigal, D. J., Venkatraman, B. R. & Manivannan, V. (2008). Acta Cryst. E64, o1848. [PMC free article] [PubMed]
  • Yachi, K., Sugiyama, Y., Sawada, Y., Iga, T., Ikeda, Y., Toda, G. & Hananon, M. (1989). Biochim. Biophys. Acta, 978, 1–7. [PubMed]

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