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

For the effect of substituents on the oxidative strengths of *N*-chloro, *N*-aryl­sulfonamides, see: Gowda & Kumar (2003[@bb2]). For the effect of substituents on the structures of *N*-(ar­yl)-amides, see: Gowda *et al.* (2004[@bb3]), on *N*-(ar­yl)-methane­sulfonamides, see: Gowda *et al.* (2007[@bb1]) and on anilinium aryl­sulfonates, see: Shakuntala *et al.* (2011[@bb6]). For restrained geometry, see: Nardelli (1999[@bb4]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~6~H~6~Cl~2~N^+^·C~6~H~4~ClO~3~S^−^·H~2~O*M* *~r~* = 372.64Triclinic,*a* = 7.7589 (8) Å*b* = 14.143 (2) Å*c* = 14.358 (2) Åα = 90.99 (1)°β = 99.56 (1)°γ = 90.68 (1)°*V* = 1553.3 (3) Å^3^*Z* = 4Mo *K*α radiationμ = 0.74 mm^−1^*T* = 293 K0.40 × 0.16 × 0.06 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~ = 0.757, *T* ~max~ = 0.95711006 measured reflections6341 independent reflections2585 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.038

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.051*wR*(*F* ^2^) = 0.081*S* = 0.846341 reflections409 parameters18 restraintsH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 0.23 e Å^−3^Δρ~min~ = −0.25 e Å^−3^

 {#d5e647}

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 datablocks I, global. DOI: [10.1107/S1600536811012463/bq2293sup1.cif](http://dx.doi.org/10.1107/S1600536811012463/bq2293sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536811012463/bq2293Isup2.hkl](http://dx.doi.org/10.1107/S1600536811012463/bq2293Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?bq2293&file=bq2293sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?bq2293sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?bq2293&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [BQ2293](http://scripts.iucr.org/cgi-bin/sendsup?bq2293)).

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

Comment
=======

The amine and sulfonate moieties are important constituents of many important compounds. As a part of studying the substituent effects on the structures of this class of compounds (Gowda & Kumar, 2003; Gowda *et al.*, 2004, 2007; Shakuntala *et al.*, 2011), in the present work, the crystal structure of 2,4-dichloroanilinium, 4-chlorobenzenesulfonate monohydrate (I) has been determined. The compound (I) showed interesting H-bonding in its crystal structure (Fig. 1). It shows 3-centre H-bonding.

The asymmetric unit of (I) contains two 2,4-dichloroanilinium cations, two 4-chlorophenylsulfonate anions and two water molecules. Three H-atoms of the positively charged NH~3~ group have two O atoms of the negatively charged sulfonate anion and one O atom of the water molecule as acceptors. Similarly two H atoms of the water molecule have two O atoms of two different negatively charged sulfonate anions as acceptors. Further, one of the O atoms of the sulfonate anion is involved in simultaneous H-bonding with two H atoms one from the positively charged NH~3~ group of 2,4-dichloroanilinium cation and the other from the water molecule.

The above behavior is in contrast to the N---H···O(S) hydrogen bonding of the three H-atoms of the positively charged NH~3~ group of 2,5-Dichloroanilinium, 4-chlorobenzenesulfonate, having three O atoms of the negatively charged sulfonate anion as acceptors, with each oxygen forming H-bonding with three H-atoms, one each from three positively charged NH~3~ groups (Shakuntala *et al.*, 2011).

The crystal packing of (I) through N1---H11N···O1, N1---H12N···O3, N1---H13N···O7, N2---H21N···O6, N2---H22N···O4 and N2---H23N···O8 hydrogen bonding (Table 1) is shown in Fig. 2.

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

The solution of chlorobenzene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 4-chlorobenzenesulfonylchloride was treated with 2,4-dichloroaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant title compound (I) was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol.

Rod like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

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

The H atoms of the NH groups were located in a difference map and later restrained to the distance N---H = 0.89 (2) Å. The H atoms of the water molecules were located in difference map and were refined with restrained geometry (Nardelli, 1999), *viz*. O---H distance was restrained to 0.85 (3) Å and H---H distance was restrained to 1.365 Å, thus leading to the angle of 107 Å. The other H atoms were positioned with idealized geometry using a riding model with C---H = 0.93 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the *U*~eq~ of the parent atom).

Figures
=======

![Molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.](e-67-o1077-fig1){#Fap1}

![Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.](e-67-o1077-fig2){#Fap2}

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

  -------------------------------------------- ---------------------------------------
  C~6~H~6~Cl~2~N^+^·C~6~H~4~ClO~3~S^−^·H~2~O   *Z* = 4
  *M~r~* = 372.64                              *F*(000) = 760
  Triclinic, *P*1                              *D*~x~ = 1.593 Mg m^−3^
  Hall symbol: -P 1                            Mo *K*α radiation, λ = 0.71073 Å
  *a* = 7.7589 (8) Å                           Cell parameters from 2092 reflections
  *b* = 14.143 (2) Å                           θ = 2.6--27.9°
  *c* = 14.358 (2) Å                           µ = 0.74 mm^−1^
  α = 90.99 (1)°                               *T* = 293 K
  β = 99.56 (1)°                               Rod, colorless
  γ = 90.68 (1)°                               0.40 × 0.16 × 0.06 mm
  *V* = 1553.3 (3) Å^3^                        
  -------------------------------------------- ---------------------------------------

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

  ------------------------------------------------------------------------------ --------------------------------------
  Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector        6341 independent reflections
  Radiation source: fine-focus sealed tube                                       2585 reflections with *I* \> 2σ(*I*)
  graphite                                                                       *R*~int~ = 0.038
  Rotation method data acquisition using ω and φ scans                           θ~max~ = 26.4°, θ~min~ = 2.7°
  Absorption correction: multi-scan (*CrysAlis RED*; Oxford Diffraction, 2009)   *h* = −7→9
  *T*~min~ = 0.757, *T*~max~ = 0.957                                             *k* = −17→17
  11006 measured reflections                                                     *l* = −16→17
  ------------------------------------------------------------------------------ --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.051   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.081                  H atoms treated by a mixture of independent and constrained refinement
  *S* = 0.84                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0253*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  6341 reflections                      (Δ/σ)~max~ = 0.008
  409 parameters                        Δρ~max~ = 0.23 e Å^−3^
  18 restraints                         Δρ~min~ = −0.25 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------

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

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Experimental. 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~   
  Cl1    1.16798 (13)   0.34833 (8)    0.45361 (8)    0.0716 (4)           
  S1     0.83184 (12)   0.59893 (7)    0.12314 (7)    0.0428 (3)           
  O1     0.9760 (3)     0.6154 (2)     0.0733 (2)     0.0761 (10)          
  O2     0.7727 (3)     0.68469 (18)   0.16210 (19)   0.0660 (8)           
  O3     0.6928 (3)     0.54560 (17)   0.06588 (16)   0.0513 (7)           
  C1     0.9151 (4)     0.5269 (3)     0.2179 (3)     0.0324 (9)           
  C2     0.9687 (4)     0.5667 (3)     0.3058 (3)     0.0473 (11)          
  H2     0.9525         0.6308         0.3163         0.057\*              
  C3     1.0466 (5)     0.5113 (3)     0.3786 (3)     0.0522 (11)          
  H3     1.0842         0.5378         0.4384         0.063\*              
  C4     1.0680 (4)     0.4174 (3)     0.3621 (3)     0.0447 (11)          
  C5     1.0119 (5)     0.3772 (3)     0.2755 (3)     0.0539 (12)          
  H5     1.0249         0.3127         0.2653         0.065\*              
  C6     0.9360 (4)     0.4332 (3)     0.2034 (3)     0.0494 (11)          
  H6     0.8983         0.4064         0.1438         0.059\*              
  Cl2    0.38560 (13)   0.65629 (7)    0.28843 (8)    0.0665 (3)           
  Cl3    0.65092 (13)   0.32972 (8)    0.42426 (8)    0.0766 (4)           
  N1     0.3174 (4)     0.5540 (2)     0.1014 (2)     0.0409 (9)           
  H11N   0.207 (3)      0.572 (2)      0.107 (2)      0.049\*              
  H12N   0.302 (4)      0.520 (2)      0.0444 (17)    0.049\*              
  H13N   0.370 (4)      0.6097 (16)    0.096 (2)      0.049\*              
  C7     0.3979 (4)     0.4994 (3)     0.1817 (3)     0.0347 (9)           
  C8     0.4360 (4)     0.5398 (3)     0.2709 (3)     0.0386 (10)          
  C9     0.5141 (4)     0.4879 (3)     0.3451 (3)     0.0478 (11)          
  H9     0.5404         0.5150         0.4053         0.057\*              
  C10    0.5531 (4)     0.3955 (3)     0.3298 (3)     0.0461 (11)          
  C11    0.5190 (4)     0.3543 (3)     0.2417 (3)     0.0494 (11)          
  H11    0.5487         0.2918         0.2319         0.059\*              
  C12    0.4399 (4)     0.4075 (3)     0.1685 (3)     0.0446 (11)          
  H12    0.4143         0.3802         0.1083         0.054\*              
  Cl4    0.59083 (14)   −0.14370 (8)   0.45223 (8)    0.0731 (4)           
  S2     0.73669 (12)   0.10495 (7)    0.12039 (7)    0.0406 (3)           
  O4     0.8462 (3)     0.05186 (18)   0.06669 (17)   0.0506 (7)           
  O5     0.8168 (3)     0.19290 (18)   0.15824 (18)   0.0641 (8)           
  O6     0.5644 (3)     0.1171 (2)     0.06778 (19)   0.0699 (9)           
  C13    0.7069 (4)     0.0346 (3)     0.2159 (3)     0.0328 (9)           
  C14    0.7135 (4)     0.0734 (3)     0.3042 (3)     0.0512 (11)          
  H14    0.7418         0.1372         0.3151         0.061\*              
  C15    0.6781 (5)     0.0181 (3)     0.3773 (3)     0.0569 (12)          
  H15    0.6818         0.0445         0.4375         0.068\*              
  C16    0.6378 (4)     −0.0750 (3)    0.3607 (3)     0.0451 (11)          
  C17    0.6327 (5)     −0.1152 (3)    0.2739 (3)     0.0551 (12)          
  H17    0.6061         −0.1792        0.2635         0.066\*              
  C18    0.6676 (5)     −0.0592 (3)    0.2012 (3)     0.0538 (12)          
  H18    0.6643         −0.0860        0.1413         0.065\*              
  Cl5    0.72539 (12)   −0.15530 (7)   0.71771 (7)    0.0605 (3)           
  Cl6    0.92906 (13)   0.17163 (8)    0.58487 (8)    0.0729 (4)           
  N2     0.7614 (4)     −0.0527 (2)    0.9026 (2)     0.0405 (9)           
  H21N   0.644 (2)      −0.062 (2)     0.900 (2)      0.049\*              
  H22N   0.785 (4)      −0.015 (2)     0.9571 (17)    0.049\*              
  H23N   0.823 (4)      −0.1072 (16)   0.908 (2)      0.049\*              
  C19    0.7992 (4)     0.0024 (3)     0.8240 (3)     0.0345 (9)           
  C20    0.7885 (4)     −0.0384 (3)    0.7357 (3)     0.0360 (10)          
  C21    0.8287 (4)     0.0129 (3)     0.6623 (3)     0.0461 (11)          
  H21    0.8226         −0.0147        0.6026         0.055\*              
  C22    0.8782 (4)     0.1061 (3)     0.6782 (3)     0.0461 (11)          
  C23    0.8912 (4)     0.1472 (3)     0.7650 (3)     0.0534 (12)          
  H23    0.9274         0.2100         0.7750         0.064\*              
  C24    0.8500 (4)     0.0946 (3)     0.8383 (3)     0.0472 (11)          
  H24    0.8570         0.1224         0.8981         0.057\*              
  O7     0.4460 (3)     0.7318 (2)     0.0649 (3)     0.0845 (11)          
  H71O   0.549 (4)      0.730 (3)      0.095 (2)      0.101\*              
  H72O   0.450 (5)      0.757 (3)      0.013 (2)      0.101\*              
  O8     0.0953 (4)     0.2321 (2)     0.0594 (2)     0.0762 (10)          
  H81O   0.079 (5)      0.256 (3)      0.007 (2)      0.091\*              
  H82O   −0.004 (4)     0.225 (3)      0.075 (3)      0.091\*              
  ------ -------------- -------------- -------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  Cl1   0.0821 (8)    0.0756 (9)    0.0568 (8)    0.0228 (6)     0.0064 (6)     0.0255 (7)
  S1    0.0377 (6)    0.0442 (7)    0.0456 (7)    0.0034 (5)     0.0033 (5)     0.0096 (5)
  O1    0.0391 (15)   0.111 (3)     0.086 (2)     0.0155 (15)    0.0234 (15)    0.063 (2)
  O2    0.0791 (19)   0.0450 (16)   0.065 (2)     0.0196 (13)    −0.0149 (15)   −0.0021 (12)
  O3    0.0536 (15)   0.0588 (18)   0.0377 (18)   −0.0021 (12)   −0.0035 (11)   0.0008 (12)
  C1    0.031 (2)     0.031 (3)     0.034 (3)     0.0002 (18)    0.0031 (17)    0.003 (2)
  C2    0.067 (3)     0.032 (3)     0.044 (3)     −0.002 (2)     0.012 (2)      0.003 (2)
  C3    0.071 (3)     0.050 (3)     0.034 (3)     −0.003 (2)     0.004 (2)      0.001 (2)
  C4    0.043 (2)     0.051 (3)     0.041 (3)     0.004 (2)      0.006 (2)      0.011 (2)
  C5    0.067 (3)     0.036 (3)     0.054 (3)     0.006 (2)      0.000 (2)      −0.007 (2)
  C6    0.063 (3)     0.038 (3)     0.040 (3)     0.009 (2)      −0.011 (2)     −0.009 (2)
  Cl2   0.0937 (8)    0.0391 (7)    0.0702 (9)    −0.0015 (6)    0.0252 (6)     −0.0063 (6)
  Cl3   0.0746 (8)    0.0844 (10)   0.0662 (9)    0.0040 (6)     −0.0051 (6)    0.0361 (7)
  N1    0.037 (2)     0.045 (3)     0.041 (2)     −0.0020 (17)   0.0088 (19)    0.0030 (19)
  C7    0.027 (2)     0.037 (3)     0.039 (3)     −0.0050 (18)   0.0020 (18)    0.009 (2)
  C8    0.043 (2)     0.033 (3)     0.041 (3)     −0.0060 (19)   0.012 (2)      −0.003 (2)
  C9    0.053 (3)     0.057 (3)     0.033 (3)     −0.011 (2)     0.005 (2)      0.001 (2)
  C10   0.041 (2)     0.047 (3)     0.049 (3)     −0.002 (2)     0.002 (2)      0.017 (2)
  C11   0.057 (3)     0.038 (3)     0.052 (3)     0.006 (2)      0.003 (2)      0.005 (2)
  C12   0.048 (2)     0.038 (3)     0.045 (3)     −0.001 (2)     0.001 (2)      −0.005 (2)
  Cl4   0.0945 (8)    0.0798 (9)    0.0496 (8)    0.0056 (7)     0.0221 (6)     0.0264 (7)
  S2    0.0369 (6)    0.0439 (7)    0.0414 (7)    −0.0017 (5)    0.0067 (5)     0.0070 (5)
  O4    0.0577 (16)   0.0560 (17)   0.0412 (18)   0.0027 (12)    0.0169 (11)    0.0013 (12)
  O5    0.0817 (18)   0.0481 (16)   0.068 (2)     −0.0198 (13)   0.0294 (15)    −0.0073 (13)
  O6    0.0351 (15)   0.103 (2)     0.072 (2)     0.0003 (14)    0.0030 (14)    0.0520 (19)
  C13   0.034 (2)     0.030 (3)     0.034 (3)     −0.0005 (18)   0.0042 (18)    −0.0015 (19)
  C14   0.066 (3)     0.043 (3)     0.042 (3)     0.005 (2)      0.003 (2)      −0.003 (2)
  C15   0.087 (3)     0.057 (4)     0.026 (3)     0.013 (3)      0.007 (2)      −0.004 (2)
  C16   0.051 (2)     0.050 (3)     0.036 (3)     0.007 (2)      0.010 (2)      0.007 (2)
  C17   0.078 (3)     0.041 (3)     0.047 (3)     −0.010 (2)     0.014 (2)      −0.001 (2)
  C18   0.076 (3)     0.052 (3)     0.035 (3)     −0.015 (2)     0.014 (2)      −0.005 (2)
  Cl5   0.0848 (8)    0.0356 (7)    0.0567 (8)    −0.0043 (6)    −0.0006 (6)    −0.0018 (6)
  Cl6   0.0835 (8)    0.0727 (9)    0.0622 (8)    −0.0099 (6)    0.0088 (6)     0.0308 (7)
  N2    0.0316 (19)   0.044 (3)     0.046 (2)     0.0005 (17)    0.0062 (19)    −0.0010 (19)
  C19   0.026 (2)     0.040 (3)     0.038 (3)     0.0024 (18)    0.0059 (18)    0.005 (2)
  C20   0.033 (2)     0.032 (3)     0.042 (3)     0.0005 (18)    0.0015 (19)    0.002 (2)
  C21   0.053 (3)     0.047 (3)     0.035 (3)     0.002 (2)      −0.001 (2)     0.001 (2)
  C22   0.041 (2)     0.049 (3)     0.047 (3)     0.000 (2)      0.004 (2)      0.017 (2)
  C23   0.060 (3)     0.036 (3)     0.062 (4)     −0.008 (2)     0.004 (2)      0.005 (3)
  C24   0.053 (3)     0.043 (3)     0.044 (3)     −0.006 (2)     0.005 (2)      −0.004 (2)
  O7    0.066 (2)     0.069 (2)     0.114 (3)     −0.0011 (18)   −0.002 (2)     0.048 (2)
  O8    0.079 (2)     0.062 (2)     0.094 (3)     0.0067 (19)    0.030 (2)      0.0388 (19)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

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

  ----------------------- ------------- ----------------------- -------------
  Cl1---C4                1.734 (4)     S2---O5                 1.441 (2)
  S1---O2                 1.439 (3)     S2---O4                 1.447 (2)
  S1---O3                 1.440 (2)     S2---C13                1.752 (4)
  S1---O1                 1.443 (2)     C13---C18               1.363 (4)
  S1---C1                 1.754 (3)     C13---C14               1.365 (5)
  C1---C6                 1.354 (4)     C14---C15               1.382 (5)
  C1---C2                 1.371 (5)     C14---H14               0.9300
  C2---C3                 1.380 (5)     C15---C16               1.358 (5)
  C2---H2                 0.9300        C15---H15               0.9300
  C3---C4                 1.362 (5)     C16---C17               1.356 (5)
  C3---H3                 0.9300        C17---C18               1.380 (5)
  C4---C5                 1.360 (5)     C17---H17               0.9300
  C5---C6                 1.372 (5)     C18---H18               0.9300
  C5---H5                 0.9300        Cl5---C20               1.721 (4)
  C6---H6                 0.9300        Cl6---C22               1.738 (4)
  Cl2---C8                1.721 (4)     N2---C19                1.451 (5)
  Cl3---C10               1.732 (4)     N2---H21N               0.910 (17)
  N1---C7                 1.455 (4)     N2---H22N               0.928 (18)
  N1---H11N               0.914 (17)    N2---H23N               0.911 (17)
  N1---H12N               0.932 (17)    C19---C24               1.360 (4)
  N1---H13N               0.896 (18)    C19---C20               1.374 (5)
  C7---C12                1.362 (4)     C20---C21               1.366 (5)
  C7---C8                 1.379 (5)     C21---C22               1.373 (5)
  C8---C9                 1.366 (5)     C21---H21               0.9300
  C9---C10                1.367 (5)     C22---C23               1.354 (5)
  C9---H9                 0.9300        C23---C24               1.377 (5)
  C10---C11               1.367 (5)     C23---H23               0.9300
  C11---C12               1.369 (5)     C24---H24               0.9300
  C11---H11               0.9300        O7---H71O               0.84 (2)
  C12---H12               0.9300        O7---H72O               0.84 (2)
  Cl4---C16               1.731 (4)     O8---H81O               0.83 (2)
  S2---O6                 1.436 (2)     O8---H82O               0.85 (2)
                                                                
  O2---S1---O3            112.90 (15)   O6---S2---O4            111.72 (16)
  O2---S1---O1            112.42 (19)   O5---S2---O4            112.72 (14)
  O3---S1---O1            111.54 (18)   O6---S2---C13           105.10 (15)
  O2---S1---C1            107.55 (17)   O5---S2---C13           107.66 (17)
  O3---S1---C1            106.54 (16)   O4---S2---C13           106.43 (16)
  O1---S1---C1            105.33 (15)   C18---C13---C14         119.3 (4)
  C6---C1---C2            119.9 (4)     C18---C13---S2          119.7 (3)
  C6---C1---S1            120.3 (3)     C14---C13---S2          120.9 (3)
  C2---C1---S1            119.7 (3)     C13---C14---C15         120.1 (4)
  C1---C2---C3            119.7 (4)     C13---C14---H14         119.9
  C1---C2---H2            120.1         C15---C14---H14         119.9
  C3---C2---H2            120.1         C16---C15---C14         119.4 (4)
  C4---C3---C2            119.3 (4)     C16---C15---H15         120.3
  C4---C3---H3            120.4         C14---C15---H15         120.3
  C2---C3---H3            120.4         C17---C16---C15         121.4 (4)
  C5---C4---C3            121.2 (4)     C17---C16---Cl4         119.3 (4)
  C5---C4---Cl1           119.7 (4)     C15---C16---Cl4         119.3 (3)
  C3---C4---Cl1           119.1 (3)     C16---C17---C18         118.7 (4)
  C4---C5---C6            118.9 (4)     C16---C17---H17         120.7
  C4---C5---H5            120.5         C18---C17---H17         120.7
  C6---C5---H5            120.5         C13---C18---C17         121.1 (4)
  C1---C6---C5            120.9 (4)     C13---C18---H18         119.5
  C1---C6---H6            119.5         C17---C18---H18         119.5
  C5---C6---H6            119.5         C19---N2---H21N         111 (2)
  C7---N1---H11N          112 (2)       C19---N2---H22N         108 (2)
  C7---N1---H12N          113 (2)       H21N---N2---H22N        100 (3)
  H11N---N1---H12N        104 (3)       C19---N2---H23N         112 (2)
  C7---N1---H13N          114 (2)       H21N---N2---H23N        114 (3)
  H11N---N1---H13N        102 (3)       H22N---N2---H23N        111 (3)
  H12N---N1---H13N        111 (3)       C24---C19---C20         119.8 (4)
  C12---C7---C8           119.3 (4)     C24---C19---N2          119.8 (4)
  C12---C7---N1           119.7 (4)     C20---C19---N2          120.5 (4)
  C8---C7---N1            121.0 (4)     C21---C20---C19         120.4 (4)
  C9---C8---C7            120.2 (4)     C21---C20---Cl5         119.9 (3)
  C9---C8---Cl2           120.1 (3)     C19---C20---Cl5         119.7 (3)
  C7---C8---Cl2           119.8 (3)     C20---C21---C22         118.9 (4)
  C8---C9---C10           119.2 (4)     C20---C21---H21         120.6
  C8---C9---H9            120.4         C22---C21---H21         120.6
  C10---C9---H9           120.4         C23---C22---C21         121.5 (4)
  C11---C10---C9          121.7 (4)     C23---C22---Cl6         119.6 (4)
  C11---C10---Cl3         119.3 (4)     C21---C22---Cl6         118.9 (3)
  C9---C10---Cl3          119.0 (3)     C22---C23---C24         119.0 (4)
  C10---C11---C12         118.2 (4)     C22---C23---H23         120.5
  C10---C11---H11         120.9         C24---C23---H23         120.5
  C12---C11---H11         120.9         C19---C24---C23         120.5 (4)
  C7---C12---C11          121.5 (4)     C19---C24---H24         119.8
  C7---C12---H12          119.2         C23---C24---H24         119.8
  C11---C12---H12         119.2         H71O---O7---H72O        108 (3)
  O6---S2---O5            112.63 (17)   H81O---O8---H82O        107 (3)
                                                                
  O2---S1---C1---C6       162.0 (3)     O6---S2---C13---C18     73.4 (3)
  O3---S1---C1---C6       40.7 (3)      O5---S2---C13---C18     −166.3 (3)
  O1---S1---C1---C6       −77.9 (3)     O4---S2---C13---C18     −45.2 (3)
  O2---S1---C1---C2       −21.8 (3)     O6---S2---C13---C14     −103.1 (3)
  O3---S1---C1---C2       −143.1 (3)    O5---S2---C13---C14     17.2 (3)
  O1---S1---C1---C2       98.3 (3)      O4---S2---C13---C14     138.3 (3)
  C6---C1---C2---C3       1.2 (5)       C18---C13---C14---C15   −0.9 (5)
  S1---C1---C2---C3       −175.0 (3)    S2---C13---C14---C15    175.6 (3)
  C1---C2---C3---C4       −0.5 (5)      C13---C14---C15---C16   0.4 (5)
  C2---C3---C4---C5       −0.8 (6)      C14---C15---C16---C17   0.4 (6)
  C2---C3---C4---Cl1      179.4 (3)     C14---C15---C16---Cl4   −179.2 (3)
  C3---C4---C5---C6       1.4 (6)       C15---C16---C17---C18   −0.7 (6)
  Cl1---C4---C5---C6      −178.8 (3)    Cl4---C16---C17---C18   179.0 (3)
  C2---C1---C6---C5       −0.7 (6)      C14---C13---C18---C17   0.7 (5)
  S1---C1---C6---C5       175.5 (3)     S2---C13---C18---C17    −175.9 (3)
  C4---C5---C6---C1       −0.6 (6)      C16---C17---C18---C13   0.1 (6)
  C12---C7---C8---C9      −0.4 (5)      C24---C19---C20---C21   0.0 (5)
  N1---C7---C8---C9       −178.9 (3)    N2---C19---C20---C21    −178.3 (3)
  C12---C7---C8---Cl2     179.3 (3)     C24---C19---C20---Cl5   179.6 (2)
  N1---C7---C8---Cl2      0.8 (4)       N2---C19---C20---Cl5    1.3 (4)
  C7---C8---C9---C10      −0.3 (5)      C19---C20---C21---C22   −0.6 (5)
  Cl2---C8---C9---C10     −180.0 (3)    Cl5---C20---C21---C22   179.8 (2)
  C8---C9---C10---C11     1.3 (6)       C20---C21---C22---C23   1.3 (5)
  C8---C9---C10---Cl3     −179.6 (2)    C20---C21---C22---Cl6   −179.9 (3)
  C9---C10---C11---C12    −1.6 (6)      C21---C22---C23---C24   −1.4 (6)
  Cl3---C10---C11---C12   179.3 (3)     Cl6---C22---C23---C24   179.8 (3)
  C8---C7---C12---C11     0.0 (5)       C20---C19---C24---C23   −0.2 (5)
  N1---C7---C12---C11     178.6 (3)     N2---C19---C24---C23    178.1 (3)
  C10---C11---C12---C7    0.9 (5)       C22---C23---C24---C19   0.8 (6)
  ----------------------- ------------- ----------------------- -------------

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

  --------------------- ---------- ---------- ----------- ---------------
  *D*---H···*A*         *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  N1---H11N···O1^i^     0.91 (2)   1.89 (2)   2.765 (4)   160 (3)
  N1---H12N···O3^ii^    0.93 (2)   1.83 (2)   2.752 (4)   171 (3)
  N1---H13N···O7        0.90 (2)   1.90 (2)   2.785 (4)   169 (3)
  N2---H21N···O6^iii^   0.91 (2)   1.92 (2)   2.777 (4)   156 (3)
  N2---H22N···O4^iv^    0.93 (2)   1.82 (2)   2.741 (4)   176 (3)
  N2---H23N···O8^iii^   0.91 (2)   1.92 (2)   2.807 (4)   164 (3)
  O7---H71O···O2        0.84 (2)   1.96 (2)   2.778 (4)   163 (4)
  O7---H72O···O6^ii^    0.84 (2)   2.13 (3)   2.879 (4)   148 (5)
  O8---H81O···O1^ii^    0.83 (2)   2.18 (3)   2.900 (4)   146 (4)
  O8---H82O···O5^i^     0.85 (2)   2.03 (2)   2.830 (4)   158 (4)
  --------------------- ---------- ---------- ----------- ---------------

Symmetry codes: (i) *x*−1, *y*, *z*; (ii) −*x*+1, −*y*+1, −*z*; (iii) −*x*+1, −*y*, −*z*+1; (iv) *x*, *y*, *z*+1.

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*           *D*---H    H⋯*A*      *D*⋯*A*     *D*---H⋯*A*
  --------------------- ---------- ---------- ----------- -------------
  N1---H11*N*⋯O1^i^     0.91 (2)   1.89 (2)   2.765 (4)   160 (3)
  N1---H12*N*⋯O3^ii^    0.93 (2)   1.83 (2)   2.752 (4)   171 (3)
  N1---H13*N*⋯O7        0.90 (2)   1.90 (2)   2.785 (4)   169 (3)
  N2---H21*N*⋯O6^iii^   0.91 (2)   1.92 (2)   2.777 (4)   156 (3)
  N2---H22*N*⋯O4^iv^    0.93 (2)   1.82 (2)   2.741 (4)   176 (3)
  N2---H23*N*⋯O8^iii^   0.91 (2)   1.92 (2)   2.807 (4)   164 (3)
  O7---H71*O*⋯O2        0.84 (2)   1.96 (2)   2.778 (4)   163 (4)
  O7---H72*O*⋯O6^ii^    0.84 (2)   2.13 (3)   2.879 (4)   148 (5)
  O8---H81*O*⋯O1^ii^    0.83 (2)   2.18 (3)   2.900 (4)   146 (4)
  O8---H82*O*⋯O5^i^     0.85 (2)   2.03 (2)   2.830 (4)   158 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .
