Related literature {#sec1}
==================

For the structures of closely related compounds, see: Manivannan *et al.* ( 2005*a* [@bb2],*b* [@bb3]); Ramachandran *et al.*(2007[@bb4]); Vennila *et al.* ( 2008[@bb9]).  For applications, see: Spungin *et al.* ( 1984[@bb8]); Yachi *et al.* ( 1989[@bb10]). 

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~16~H~13~NO~3~S*M* *~r~* = 299.33Monoclinic,*a* = 8.4558 (2) Å*b* = 8.6712 (3) Å*c* = 19.5915 (6) Åβ = 100.321 (2)°*V* = 1413.24 (7) Å^3^*Z* = 4Mo *K*α radiationμ = 0.24 mm^−1^*T* = 295 (2) K0.30 × 0.25 × 0.20 mm

### Data collection {#sec2.1.2}

Bruker Kappa APEXII diffractometerAbsorption correction: multi-scan (*SADABS*; Sheldrick, 1996[@bb5]) *T* ~min~ = 0.932, *T* ~max~ = 0.95419808 measured reflections4981 independent reflections3126 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.023

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.055*wR*(*F* ^2^) = 0.174*S* = 1.054981 reflections190 parametersH-atom parameters constrainedΔρ~max~ = 0.46 e Å^−3^Δρ~min~ = −0.44 e Å^−3^

 {#d5e480}

Data collection: *APEX2* (Bruker, 2004[@bb1]); cell refinement: *SAINT* (Bruker, 2004[@bb1]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb6]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb6]); molecular graphics: *PLATON* (Spek, 2003[@bb7]); software used to prepare material for publication: *SHELXL97*. 

Supplementary Material
======================

Crystal structure: contains datablocks I, global.  DOI: [10.1107/S1600536808041032/gk2179sup1.cif](http://dx.doi.org/10.1107/S1600536808041032/gk2179sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536808041032/gk2179Isup2.hkl](http://dx.doi.org/10.1107/S1600536808041032/gk2179Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?gk2179&file=gk2179sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?gk2179sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?gk2179&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [GK2179](http://scripts.iucr.org/cgi-bin/sendsup?gk2179)). 

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

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 {#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 {#refinement}
==========

H atoms were positioned geometrically and refined using riding model with C---H = 0.93 Å and *U*~iso~(H) = 1.2Ueq(C) for aromatic C---H and N---H = 0.86 Å and *U*~iso~(H) = 1.2Ueq(N) for N---H.

Figures
=======

![ The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.](e-65-00o72-fig1){#Fap1}

![ The packing viewed down the b axis.  Hydrogen bonds are shown as dashed lines.  H atoms not involved in hydrogen bonding have been omitted.](e-65-00o72-fig2){#Fap2}

Crystal data {#tablewrapcrystaldatalong}
============

  ------------------------- ---------------------------------------
  C~16~H~13~NO~3~S          *F*(000) = 624
  *M~r~* = 299.33           *D*~x~ = 1.407 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ybc      Cell parameters from 4818 reflections
  *a* = 8.4558 (2) Å        θ = 2.2--25.4°
  *b* = 8.6712 (3) Å        µ = 0.24 mm^−1^
  *c* = 19.5915 (6) Å       *T* = 295 K
  β = 100.321 (2)°          Block, brown
  *V* = 1413.24 (7) Å^3^    0.30 × 0.25 × 0.20 mm
  *Z* = 4                   
  ------------------------- ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  --------------------------------------------------------------- --------------------------------------
  Bruker Kappa APEX2 diffractometer                               4981 independent reflections
  Radiation source: fine-focus sealed tube                        3126 reflections with *I* \> 2σ(*I*)
  graphite                                                        *R*~int~ = 0.023
  ω and φ scans                                                   θ~max~ = 32.2°, θ~min~ = 2.1°
  Absorption correction: multi-scan (*SADABS*; Sheldrick, 1996)   *h* = −12→10
  *T*~min~ = 0.932, *T*~max~ = 0.954                              *k* = −12→11
  19808 measured reflections                                      *l* = −21→29
  --------------------------------------------------------------- --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.055   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.174                  H-atom parameters constrained
  *S* = 1.05                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0763*P*)^2^ + 0.3485*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  4981 reflections                      (Δ/σ)~max~ \< 0.001
  190 parameters                        Δρ~max~ = 0.46 e Å^−3^
  0 restraints                          Δρ~min~ = −0.44 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  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 *F*^2^ against ALL reflections.  The weighted *R*-factor *wR* and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> σ(*F*^2^) is used only for calculating *R*-factors(gt) *etc*.  and is not relevant to the choice of reflections for refinement. * R*-factors based on *F*^2^ 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 (Å^2^) {#tablewrapcoords}
==================================================================================================

  ----- -------------- -------------- --------------- -------------------- --
        *x*            *y*            *z*             *U*~iso~\*/*U*~eq~   
  C1    0.34222 (19)   0.8581 (2)     0.10826 (8)     0.0475 (4)           
  C2    0.2573 (3)     0.9698 (3)     0.13547 (12)    0.0688 (6)           
  H2    0.2543         0.9701         0.1827          0.083\*              
  C3    0.1749 (3)     1.0837 (3)     0.09239 (19)    0.0876 (8)           
  H3    0.1173         1.1596         0.1109          0.105\*              
  C4    0.1793 (3)     1.0828 (3)     0.02504 (18)    0.0858 (8)           
  H4    0.1241         1.1593         −0.0029         0.103\*              
  C5    0.2639 (2)     0.9713 (2)     −0.00569 (11)   0.0634 (5)           
  C6    0.2687 (4)     0.9715 (4)     −0.07762 (13)   0.0910 (9)           
  H6    0.2122         1.0468         −0.1058         0.109\*              
  C7    0.3515 (4)     0.8673 (4)     −0.10559 (13)   0.1015 (12)          
  H7    0.3537         0.8711         −0.1529         0.122\*              
  C8    0.4342 (4)     0.7536 (3)     −0.06564 (14)   0.0872 (9)           
  H8    0.4913         0.6808         −0.0863         0.105\*              
  C9    0.4342 (2)     0.7451 (2)     0.00414 (11)    0.0619 (5)           
  H9    0.4904         0.6666         0.0303          0.074\*              
  C10   0.34948 (19)   0.85482 (19)   0.03643 (8)     0.0458 (4)           
  C11   0.21070 (19)   0.52112 (19)   0.14424 (9)     0.0466 (4)           
  C12   0.0822 (2)     0.5617 (2)     0.09445 (10)    0.0595 (5)           
  H12   0.0949         0.6176         0.0553          0.071\*              
  C13   −0.0674 (2)    0.5150 (3)     0.10555 (12)    0.0696 (6)           
  H13   −0.1582        0.5414         0.0734          0.084\*              
  C14   −0.0850 (2)    0.4309 (2)     0.16279 (11)    0.0637 (5)           
  H14   −0.1874        0.4025         0.1692          0.076\*              
  C15   0.0471 (2)     0.3876 (2)     0.21112 (10)    0.0561 (4)           
  C16   0.1979 (2)     0.4357 (2)     0.20153 (9)     0.0511 (4)           
  H16   0.2890         0.4101         0.2336          0.061\*              
  O1    0.36734 (15)   0.56180 (15)   0.13433 (7)     0.0580 (3)           
  O2    0.3993 (2)     0.7447 (2)     0.23185 (7)     0.0915 (6)           
  O3    0.60456 (18)   0.7106 (2)     0.15880 (10)    0.0903 (6)           
  N1    0.0316 (3)     0.3014 (3)     0.26868 (11)    0.0868 (6)           
  H1A   −0.0621        0.2733         0.2752          0.104\*              
  H1B   0.1156         0.2758         0.2981          0.104\*              
  S1    0.44040 (6)    0.72128 (7)    0.16539 (2)     0.06166 (18)         
  ----- -------------- -------------- --------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  C1    0.0464 (8)    0.0490 (9)    0.0497 (8)    −0.0131 (7)    0.0153 (6)     −0.0086 (7)
  C2    0.0679 (12)   0.0677 (13)   0.0789 (13)   −0.0188 (10)   0.0346 (10)    −0.0268 (11)
  C3    0.0697 (14)   0.0536 (13)   0.144 (3)     0.0011 (10)    0.0312 (15)    −0.0233 (15)
  C4    0.0699 (14)   0.0511 (12)   0.130 (2)     −0.0040 (10)   0.0007 (14)    0.0086 (14)
  C5    0.0621 (11)   0.0556 (11)   0.0683 (12)   −0.0236 (9)    0.0003 (9)     0.0073 (9)
  C6    0.1060 (19)   0.0930 (19)   0.0634 (13)   −0.0531 (16)   −0.0135 (13)   0.0241 (13)
  C7    0.136 (3)     0.118 (2)     0.0525 (13)   −0.082 (2)     0.0230 (15)    −0.0135 (15)
  C8    0.1037 (19)   0.0958 (19)   0.0737 (14)   −0.0525 (16)   0.0469 (14)    −0.0426 (14)
  C9    0.0619 (11)   0.0660 (12)   0.0638 (11)   −0.0206 (9)    0.0276 (9)     −0.0226 (9)
  C10   0.0451 (8)    0.0451 (8)    0.0482 (8)    −0.0160 (6)    0.0112 (6)     −0.0062 (6)
  C11   0.0461 (8)    0.0416 (8)    0.0523 (9)    −0.0039 (6)    0.0095 (6)     −0.0014 (7)
  C12   0.0603 (10)   0.0606 (11)   0.0536 (10)   −0.0068 (9)    −0.0006 (8)    0.0050 (8)
  C13   0.0519 (10)   0.0769 (14)   0.0725 (13)   −0.0074 (9)    −0.0091 (9)    −0.0047 (11)
  C14   0.0522 (10)   0.0598 (11)   0.0798 (13)   −0.0175 (8)    0.0139 (9)     −0.0150 (10)
  C15   0.0643 (10)   0.0438 (9)    0.0640 (11)   −0.0099 (8)    0.0214 (9)     −0.0058 (8)
  C16   0.0524 (9)    0.0452 (9)    0.0546 (9)    −0.0002 (7)    0.0068 (7)     0.0035 (7)
  O1    0.0501 (6)    0.0556 (7)    0.0704 (8)    −0.0023 (5)    0.0165 (6)     0.0074 (6)
  O2    0.1164 (14)   0.1138 (14)   0.0419 (7)    −0.0494 (11)   0.0078 (8)     −0.0014 (8)
  O3    0.0456 (8)    0.1086 (14)   0.1099 (14)   −0.0144 (8)    −0.0046 (8)    0.0307 (11)
  N1    0.0905 (14)   0.0891 (15)   0.0865 (14)   −0.0159 (11)   0.0316 (11)    0.0238 (11)
  S1    0.0536 (3)    0.0762 (4)    0.0524 (3)    −0.0199 (2)    0.00177 (19)   0.0072 (2)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

Geometric parameters (Å, °) {#tablewrapgeomlong}
===========================

  -------------------- -------------- ----------------------- --------------
  C1---C2              1.370 (3)      C9---H9                 0.9300
  C1---C10             1.420 (2)      C11---C16               1.365 (2)
  C1---S1              1.7368 (19)    C11---C12               1.370 (2)
  C2---C3              1.401 (4)      C11---O1                1.4173 (19)
  C2---H2              0.9300         C12---C13               1.382 (3)
  C3---C4              1.327 (4)      C12---H12               0.9300
  C3---H3              0.9300         C13---C14               1.368 (3)
  C4---C5              1.401 (4)      C13---H13               0.9300
  C4---H4              0.9300         C14---C15               1.381 (3)
  C5---C6              1.417 (3)      C14---H14               0.9300
  C5---C10             1.418 (3)      C15---N1                1.378 (3)
  C6---C7              1.321 (5)      C15---C16               1.386 (2)
  C6---H6              0.9300         C16---H16               0.9300
  C7---C8              1.370 (5)      O1---S1                 1.5905 (14)
  C7---H7              0.9300         O2---S1                 1.4212 (16)
  C8---C9              1.369 (3)      O3---S1                 1.4199 (16)
  C8---H8              0.9300         N1---H1A                0.8600
  C9---C10             1.408 (3)      N1---H1B                0.8600
                                                              
  C2---C1---C10        121.24 (18)    C5---C10---C1           117.02 (17)
  C2---C1---S1         117.12 (15)    C16---C11---C12         123.72 (16)
  C10---C1---S1        121.63 (13)    C16---C11---O1          117.47 (15)
  C1---C2---C3         120.2 (2)      C12---C11---O1          118.71 (16)
  C1---C2---H2         119.9          C11---C12---C13         116.40 (18)
  C3---C2---H2         119.9          C11---C12---H12         121.8
  C4---C3---C2         119.7 (2)      C13---C12---H12         121.8
  C4---C3---H3         120.2          C14---C13---C12         121.48 (18)
  C2---C3---H3         120.2          C14---C13---H13         119.3
  C3---C4---C5         122.6 (2)      C12---C13---H13         119.3
  C3---C4---H4         118.7          C13---C14---C15         120.92 (18)
  C5---C4---H4         118.7          C13---C14---H14         119.5
  C4---C5---C6         122.3 (3)      C15---C14---H14         119.5
  C4---C5---C10        119.2 (2)      N1---C15---C14          121.64 (19)
  C6---C5---C10        118.5 (2)      N1---C15---C16          119.91 (19)
  C7---C6---C5         121.6 (3)      C14---C15---C16         118.43 (17)
  C7---C6---H6         119.2          C11---C16---C15         119.01 (16)
  C5---C6---H6         119.2          C11---C16---H16         120.5
  C6---C7---C8         120.6 (2)      C15---C16---H16         120.5
  C6---C7---H7         119.7          C11---O1---S1           118.20 (11)
  C8---C7---H7         119.7          C15---N1---H1A          120.0
  C9---C8---C7         121.2 (3)      C15---N1---H1B          120.0
  C9---C8---H8         119.4          H1A---N1---H1B          120.0
  C7---C8---H8         119.4          O3---S1---O2            119.75 (11)
  C8---C9---C10        120.2 (2)      O3---S1---O1            103.16 (10)
  C8---C9---H9         119.9          O2---S1---O1            109.45 (9)
  C10---C9---H9        119.9          O3---S1---C1            110.36 (9)
  C9---C10---C5        117.90 (18)    O2---S1---C1            108.99 (11)
  C9---C10---C1        125.09 (18)    O1---S1---C1            103.85 (7)
                                                              
  C10---C1---C2---C3   0.2 (3)        C16---C11---C12---C13   1.8 (3)
  S1---C1---C2---C3    −179.87 (16)   O1---C11---C12---C13    178.00 (17)
  C1---C2---C3---C4    0.1 (3)        C11---C12---C13---C14   −0.9 (3)
  C2---C3---C4---C5    0.1 (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---C16   2.1 (3)
  C4---C5---C6---C7    178.7 (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---C8    0.9 (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---C5   0.8 (3)        C12---C11---O1---S1     91.97 (18)
  C8---C9---C10---C1   −179.44 (16)   C11---O1---S1---O3      168.69 (12)
  C4---C5---C10---C9   −179.52 (17)   C11---O1---S1---O2      40.15 (16)
  C6---C5---C10---C9   −0.3 (2)       C11---O1---S1---C1      −76.12 (13)
  C4---C5---C10---C1   0.7 (2)        C2---C1---S1---O3       −127.86 (16)
  C6---C5---C10---C1   179.93 (16)    C10---C1---S1---O3      52.09 (16)
  C2---C1---C10---C9   179.68 (17)    C2---C1---S1---O2       5.58 (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---O1       122.16 (14)
  S1---C1---C10---C5   179.50 (12)    C10---C1---S1---O1      −57.89 (14)
  -------------------- -------------- ----------------------- --------------

Hydrogen-bond geometry (Å, °) {#tablewraphbondslong}
=============================

  ------------------ --------- --------- ----------- ---------------
  *D*---H···*A*      *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C2---H2···O2       0.93      2.41      2.829 (3)   107
  C9---H9···O3       0.93      2.56      3.127 (3)   120
  N1---H1B···O3^i^   0.86      2.43      3.246 (3)   158
  C7---H7···O2^ii^   0.93      2.56      3.422 (3)   154
  ------------------ --------- --------- ----------- ---------------

Symmetry codes: (i) −*x*+1, *y*−1/2, −*z*+1/2; (ii) *x*, −*y*+3/2, *z*−1/2. 

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*        *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  ------------------ --------- ------- ----------- -------------
  C2---H2⋯O2         0.93      2.41    2.829 (3)   107
  C9---H9⋯O3         0.93      2.56    3.127 (3)   120
  N1---H1*B*⋯O3^i^   0.86      2.43    3.246 (3)   158
  C7---H7⋯O2^ii^     0.93      2.56    3.422 (3)   154

Symmetry codes: (i) ; (ii) .