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

For our studies on the effects of substituents on the structures and other aspects of *N*-(ar­yl)-amides, see: Gowda *et al.* ( 2000[@bb2]); Saraswathi *et al.* ( 2011[@bb6]), of *N*-chloro­aryl­amides, see: Gowda & Rao (1989[@bb3]); Jyothi & Gowda (2004[@bb4]) and of *N*-bromo­aryl­sulfonamides, see: Gowda & Mahadevappa (1983[@bb1]); Usha & Gowda (2006[@bb9]). 

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~11~H~13~NO~5~S*M* *~r~* = 271.28Monoclinic,*a* = 10.2496 (9) Å*b* = 17.041 (2) Å*c* = 7.4721 (6) Åβ = 101.909 (9)°*V* = 1277.0 (2) Å^3^*Z* = 4Mo *K*α radiationμ = 0.27 mm^−1^*T* = 293 K0.48 × 0.32 × 0.16 mm

### Data collection   {#sec2.1.2}

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detectorAbsorption correction: multi-scan (*CrysAlis RED*; Oxford Diffraction, 2009[@bb5]) *T* ~min~ = 0.883, *T* ~max~ = 0.9594739 measured reflections2597 independent reflections2107 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.014

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.046*wR*(*F* ^2^) = 0.110*S* = 1.122597 reflections170 parameters2 restraintsH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 0.23 e Å^−3^Δρ~min~ = −0.32 e Å^−3^

 {#d5e438}

Data collection: *CrysAlis CCD* (Oxford Diffraction, 2009[@bb5]); cell refinement: *CrysAlis RED* (Oxford Diffraction, 2009[@bb5]); data reduction: *CrysAlis RED*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb7]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb7]); molecular graphics: *PLATON* (Spek, 2009[@bb8]); software used to prepare material for publication: *SHELXL97*. 

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

Crystal structure: contains datablock(s) I, global.  DOI: [10.1107/S1600536812023276/rz2761sup1.cif](http://dx.doi.org/10.1107/S1600536812023276/rz2761sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536812023276/rz2761Isup2.hkl](http://dx.doi.org/10.1107/S1600536812023276/rz2761Isup2.hkl)

Supplementary material file.  DOI: [10.1107/S1600536812023276/rz2761Isup3.cml](http://dx.doi.org/10.1107/S1600536812023276/rz2761Isup3.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?rz2761&file=rz2761sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?rz2761sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?rz2761&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [RZ2761](http://scripts.iucr.org/cgi-bin/sendsup?rz2761)). 

HP thanks the Department of Science and Technology, Government of India, New Delhi, for a research fellowship under its INSPIRE Program.  BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC--BSR one-time grant to faculty. 

Comment
=======

As part of our studies on the substituent effects on the structures and other aspects of *N*-(aryl)-amides (Gowda *et al.*,  2000; Saraswathi *et al.*,  2011); *N*-chloroarylsulfonamides (Gowda & Rao, 1989; Jyothi & Gowda, 2004) and *N*-bromoaryl- sulfonamides (Gowda & Mahadevappa, 1983; Usha & Gowda, 2006), in the present work, the crystal structure of *N*-(4-methylphenylsulfonyl)succinamic acid has been determined (Fig.  1).  The conformations of the N---H and C=O bonds in the amide segment are *anti* to each other.  Further, the amide C═O and the carboxyl C═O of the acid segment orient themselves away from each other, in contrast to the *anti* conformation observed between the the amide oxygen and the carboxyl oxygen in *N*-(4-methylphenyl)-succinamic acid (I) (Saraswathi *et al.*,  2011).  But both the amide oxygen and the carboxyl oxygen are *anti* to the H atoms on the adjacent --CH~2~ groups, in both the compounds. 

In the title compound, the C═O and O---H bonds of the acid group are in *syn* position to each other, similar to that observed in (I).  The molecule is bent at the S-atom with the C1--S1--N1--C7 torsion angle of 79.2 (1)°.  Further, the dihedral angle between the phenyl ring and the amide group is 69.0 (2)°.  In the crystal, the pairs of O---H···O and N---H···O intermolecular hydrogen bonds link the molecules into layers parallel to the *bc* plane (Table 1, Fig.  2). 

Experimental {#experimental}
============

Succinic anhydride (0.015 mole) and 4-dimethylaminopyridine (0.01 mole) were added to a solution of *p*-toluenesulfonamide (0.01 mole) in dichloromethane.  The reaction mixture was strirred for 18 h at room temperature and set aside for completion of the reaction.  The reaction mixture was concentrated to dryness.  The resultant title compound was washed with dilute HCl and then with water thoroughly, to remove the unreacted base and the succinic anhydride.  It was recrystallized to constant melting point from ethyl acetate (173--175 °C).  The purity of the compound was checked and characterized by its infrared spectrum.  Prism-like colourless single crystals used in X-ray diffraction studies were grown by slow evaporation of an ethyl acetate solution at room temperature. 

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

The H atoms of the NH group and the OH group were located in a difference Fourier map and later restrained to the distances of N---H = 0.86 (2) Å and O---H = 0.82 (2) Å, respectively.  The other H atoms were positioned with idealized geometry using a riding model with the aromatic C---H = 0.93 Å, methyl C---H = 0.96 Å and methylene C---H = 0.97 Å. All H atoms were refined with isotropic displacement parameters set at 1.2 *U*~eq~(C-aromatic, N) and 1.5 *U*~eq~(*C*-methyl). 

Figures
=======

![ The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.](e-68-o1885-fig1){#Fap1}

![ The molecular packing of the title compound with hydrogen bonding shown as dashed lines.](e-68-o1885-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~11~H~13~NO~5~S          *F*(000) = 568
  *M~r~* = 271.28           *D*~x~ = 1.411 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ybc      Cell parameters from 2495 reflections
  *a* = 10.2496 (9) Å       θ = 3.0--27.6°
  *b* = 17.041 (2) Å        µ = 0.27 mm^−1^
  *c* = 7.4721 (6) Å        *T* = 293 K
  β = 101.909 (9)°          Prism, colourless
  *V* = 1277.0 (2) Å^3^     0.48 × 0.32 × 0.16 mm
  *Z* = 4                   
  ------------------------- ---------------------------------------

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

  ------------------------------------------------------------------------------ --------------------------------------
  Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector        2597 independent reflections
  Radiation source: fine-focus sealed tube                                       2107 reflections with *I* \> 2σ(*I*)
  Graphite monochromator                                                         *R*~int~ = 0.014
  Rotation method data acquisition using ω and phi scans                         θ~max~ = 26.4°, θ~min~ = 3.0°
  Absorption correction: multi-scan (*CrysAlis RED*; Oxford Diffraction, 2009)   *h* = −12→11
  *T*~min~ = 0.883, *T*~max~ = 0.959                                             *k* = −21→8
  4739 measured reflections                                                      *l* = −9→9
  ------------------------------------------------------------------------------ --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.046   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.110                  H atoms treated by a mixture of independent and constrained refinement
  *S* = 1.12                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.034*P*)^2^ + 0.9166*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  2597 reflections                      (Δ/σ)~max~ = 0.001
  170 parameters                        Δρ~max~ = 0.23 e Å^−3^
  2 restraints                          Δρ~min~ = −0.32 e Å^−3^
  ------------------------------------- ------------------------------------------------------------------------------------------------

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

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Experimental.  Absorption correction: CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 
  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     0.1649 (2)     0.82620 (14)   0.0924 (3)    0.0398 (5)           
  C2     0.1077 (3)     0.75638 (15)   0.0207 (4)    0.0507 (6)           
  H2     0.1604         0.7126         0.0132        0.061\*              
  C3     −0.0291 (3)    0.75296 (17)   −0.0394 (4)   0.0625 (7)           
  H3     −0.0682        0.7063         −0.0881       0.075\*              
  C4     −0.1092 (3)    0.81770 (18)   −0.0286 (4)   0.0607 (7)           
  C5     −0.0496 (3)    0.88660 (16)   0.0469 (4)    0.0582 (7)           
  H5     −0.1025        0.9301         0.0572        0.070\*              
  C6     0.0864 (3)     0.89152 (14)   0.1068 (4)    0.0482 (6)           
  H6     0.1255         0.9381         0.1563        0.058\*              
  C7     0.3668 (2)     0.93791 (13)   −0.0993 (3)   0.0349 (5)           
  C8     0.4086 (2)     0.94773 (14)   −0.2799 (3)   0.0394 (5)           
  H8A    0.3879         0.9001         −0.3514       0.047\*              
  H8B    0.5042         0.9557         −0.2582       0.047\*              
  C9     0.3388 (2)     1.01660 (14)   −0.3874 (3)   0.0439 (6)           
  H9A    0.3582         1.0638         −0.3143       0.053\*              
  H9B    0.3743         1.0236         −0.4971       0.053\*              
  C10    0.1912 (2)     1.00645 (14)   −0.4408 (3)   0.0419 (5)           
  C11    −0.2586 (3)    0.8130 (2)     −0.0975 (6)   0.0995 (13)          
  H11A   −0.2856        0.7590         −0.1091       0.119\*              
  H11B   −0.2822        0.8382         −0.2147       0.119\*              
  H11C   −0.3029        0.8389         −0.0126       0.119\*              
  N1     0.3902 (2)     0.86326 (11)   −0.0248 (2)   0.0387 (4)           
  H1N    0.404 (3)      0.8261 (12)    −0.090 (3)    0.046\*              
  O1     0.39301 (18)   0.75502 (11)   0.1880 (2)    0.0565 (5)           
  O2     0.37311 (18)   0.89014 (11)   0.2992 (2)    0.0558 (5)           
  O3     0.32175 (17)   0.99012 (10)   −0.0214 (2)   0.0479 (4)           
  O4     0.13237 (16)   0.94917 (10)   −0.4003 (3)   0.0552 (5)           
  O5     0.13192 (19)   1.06525 (12)   −0.5367 (3)   0.0672 (6)           
  H5O    0.0496 (18)    1.0596 (19)    −0.557 (4)    0.081\*              
  S1     0.33860 (6)    0.83267 (4)    0.15920 (7)   0.04120 (18)         
  ------ -------------- -------------- ------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- ------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^       *U*^23^
  C1    0.0465 (13)   0.0405 (13)   0.0342 (11)   −0.0018 (10)   0.0130 (9)    0.0004 (10)
  C2    0.0567 (15)   0.0388 (13)   0.0565 (15)   0.0028 (12)    0.0116 (12)   −0.0042 (12)
  C3    0.0639 (18)   0.0487 (16)   0.0723 (19)   −0.0113 (14)   0.0080 (14)   −0.0089 (14)
  C4    0.0482 (15)   0.0634 (18)   0.0701 (18)   −0.0024 (13)   0.0112 (13)   0.0047 (15)
  C5    0.0537 (16)   0.0479 (15)   0.0771 (19)   0.0076 (13)    0.0230 (14)   0.0025 (14)
  C6    0.0562 (15)   0.0359 (13)   0.0564 (15)   −0.0021 (11)   0.0209 (12)   −0.0030 (11)
  C7    0.0315 (11)   0.0392 (12)   0.0328 (11)   −0.0044 (9)    0.0038 (9)    −0.0022 (9)
  C8    0.0365 (12)   0.0479 (13)   0.0336 (11)   −0.0005 (10)   0.0072 (9)    0.0029 (10)
  C9    0.0405 (12)   0.0479 (14)   0.0430 (12)   −0.0051 (11)   0.0082 (10)   0.0080 (11)
  C10   0.0464 (13)   0.0400 (13)   0.0376 (12)   0.0007 (11)    0.0047 (10)   0.0042 (10)
  C11   0.054 (2)     0.098 (3)     0.140 (4)     −0.0050 (19)   0.003 (2)     −0.001 (3)
  N1    0.0485 (11)   0.0360 (10)   0.0341 (10)   0.0027 (9)     0.0142 (8)    −0.0011 (8)
  O1    0.0609 (11)   0.0531 (11)   0.0559 (11)   0.0110 (9)     0.0129 (9)    0.0202 (9)
  O2    0.0649 (11)   0.0689 (12)   0.0326 (8)    −0.0113 (10)   0.0075 (8)    −0.0062 (8)
  O3    0.0580 (10)   0.0423 (10)   0.0467 (9)    0.0046 (8)     0.0181 (8)    −0.0041 (8)
  O4    0.0420 (9)    0.0466 (10)   0.0718 (12)   −0.0054 (8)    −0.0001 (8)   0.0162 (9)
  O5    0.0451 (10)   0.0579 (12)   0.0924 (15)   0.0011 (9)     0.0001 (10)   0.0301 (11)
  S1    0.0478 (3)    0.0445 (3)    0.0315 (3)    −0.0001 (3)    0.0087 (2)    0.0046 (2)
  ----- ------------- ------------- ------------- -------------- ------------- --------------

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

  -------------------- ------------- -------------------- --------------
  C1---C2              1.385 (3)     C8---H8A             0.9700
  C1---C6              1.390 (3)     C8---H8B             0.9700
  C1---S1              1.750 (2)     C9---C10             1.493 (3)
  C2---C3              1.382 (4)     C9---H9A             0.9700
  C2---H2              0.9300        C9---H9B             0.9700
  C3---C4              1.387 (4)     C10---O4             1.218 (3)
  C3---H3              0.9300        C10---O5             1.307 (3)
  C4---C5              1.388 (4)     C11---H11A           0.9600
  C4---C11             1.514 (4)     C11---H11B           0.9600
  C5---C6              1.377 (4)     C11---H11C           0.9600
  C5---H5              0.9300        N1---S1              1.6559 (19)
  C6---H6              0.9300        N1---H1N             0.828 (16)
  C7---O3              1.206 (3)     O1---S1              1.4349 (19)
  C7---N1              1.390 (3)     O2---S1              1.4234 (18)
  C7---C8              1.507 (3)     O5---H5O             0.832 (18)
  C8---C9              1.516 (3)                          
                                                          
  C2---C1---C6         120.8 (2)     H8A---C8---H8B       107.9
  C2---C1---S1         119.28 (19)   C10---C9---C8        113.14 (19)
  C6---C1---S1         119.88 (19)   C10---C9---H9A       109.0
  C3---C2---C1         118.8 (2)     C8---C9---H9A        109.0
  C3---C2---H2         120.6         C10---C9---H9B       109.0
  C1---C2---H2         120.6         C8---C9---H9B        109.0
  C2---C3---C4         121.3 (3)     H9A---C9---H9B       107.8
  C2---C3---H3         119.3         O4---C10---O5        123.6 (2)
  C4---C3---H3         119.3         O4---C10---C9        123.6 (2)
  C3---C4---C5         118.7 (3)     O5---C10---C9        112.9 (2)
  C3---C4---C11        120.5 (3)     C4---C11---H11A      109.5
  C5---C4---C11        120.8 (3)     C4---C11---H11B      109.5
  C6---C5---C4         121.0 (2)     H11A---C11---H11B    109.5
  C6---C5---H5         119.5         C4---C11---H11C      109.5
  C4---C5---H5         119.5         H11A---C11---H11C    109.5
  C5---C6---C1         119.3 (2)     H11B---C11---H11C    109.5
  C5---C6---H6         120.3         C7---N1---S1         124.26 (16)
  C1---C6---H6         120.3         C7---N1---H1N        120.1 (18)
  O3---C7---N1         122.2 (2)     S1---N1---H1N        111.6 (18)
  O3---C7---C8         123.9 (2)     C10---O5---H5O       111 (2)
  N1---C7---C8         113.78 (19)   O2---S1---O1         119.62 (11)
  C7---C8---C9         111.76 (19)   O2---S1---N1         108.68 (10)
  C7---C8---H8A        109.3         O1---S1---N1         103.54 (10)
  C9---C8---H8A        109.3         O2---S1---C1         109.68 (11)
  C7---C8---H8B        109.3         O1---S1---C1         109.01 (11)
  C9---C8---H8B        109.3         N1---S1---C1         105.27 (10)
                                                          
  C6---C1---C2---C3    1.0 (4)       C8---C9---C10---O4   0.8 (3)
  S1---C1---C2---C3    −177.0 (2)    C8---C9---C10---O5   −178.6 (2)
  C1---C2---C3---C4    −0.2 (4)      O3---C7---N1---S1    10.0 (3)
  C2---C3---C4---C5    −0.9 (5)      C8---C7---N1---S1    −172.55 (15)
  C2---C3---C4---C11   179.2 (3)     C7---N1---S1---O2    −48.4 (2)
  C3---C4---C5---C6    1.3 (4)       C7---N1---S1---O1    −176.60 (18)
  C11---C4---C5---C6   −178.8 (3)    C7---N1---S1---C1    69.0 (2)
  C4---C5---C6---C1    −0.5 (4)      C2---C1---S1---O2    −153.06 (19)
  C2---C1---C6---C5    −0.7 (4)      C6---C1---S1---O2    28.8 (2)
  S1---C1---C6---C5    177.4 (2)     C2---C1---S1---O1    −20.3 (2)
  O3---C7---C8---C9    −23.2 (3)     C6---C1---S1---O1    161.55 (18)
  N1---C7---C8---C9    159.36 (19)   C2---C1---S1---N1    90.2 (2)
  C7---C8---C9---C10   −63.7 (3)     C6---C1---S1---N1    −87.9 (2)
  -------------------- ------------- -------------------- --------------

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

  --------------------- ---------- ---------- ----------- ---------------
  *D*---H···*A*         *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  N1---H1*N*···O1^i^    0.83 (2)   2.14 (2)   2.948 (2)   164 (2)
  O5---H5*O*···O4^ii^   0.83 (2)   1.83 (2)   2.663 (3)   178 (3)
  --------------------- ---------- ---------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*         *D*---H    H⋯*A*      *D*⋯*A*     *D*---H⋯*A*
  ------------------- ---------- ---------- ----------- -------------
  N1---H1*N*⋯O1^i^    0.83 (2)   2.14 (2)   2.948 (2)   164 (2)
  O5---H5*O*⋯O4^ii^   0.83 (2)   1.83 (2)   2.663 (3)   178 (3)

Symmetry codes: (i) ; (ii) .