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

For background concerning the medical applications of benzothia­zole compounds, see: Alfred & Sawhney (1968[@bb1]); Hutchinson & Jennings (2002[@bb3]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~13~H~10~N~2~S*M* *~r~* = 226.29Triclinic,*a* = 8.7038 (5) Å*b* = 9.5933 (6) Å*c* = 14.5144 (9) Åα = 70.720 (1)°β = 77.326 (1)°γ = 73.170 (1)°*V* = 1084.63 (11) Å^3^*Z* = 4Mo *K*α radiationμ = 0.27 mm^−1^*T* = 298 (2) K0.30 × 0.20 × 0.20 mm

### Data collection {#sec2.1.2}

Bruker SMART CCD diffractometerAbsorption correction: multi-scan (*SADABS*; Sheldrick, 2003[@bb4]) *T* ~min~ = 0.924, *T* ~max~ = 0.9486984 measured reflections4199 independent reflections3123 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.036

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.046*wR*(*F* ^2^) = 0.115*S* = 0.974199 reflections301 parameters4 restraintsH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 0.29 e Å^−3^Δρ~min~ = −0.23 e Å^−3^

 {#d5e416}

Data collection: *SMART* (Bruker, 2001[@bb2]); cell refinement: *SAINT-Plus* (Bruker, 2001[@bb2]); data reduction: *SAINT-Plus*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb5]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb5]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb5]); software used to prepare material for publication: *SHELXTL*.

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536808031565/bi2301sup1.cif](http://dx.doi.org/10.1107/S1600536808031565/bi2301sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536808031565/bi2301Isup2.hkl](http://dx.doi.org/10.1107/S1600536808031565/bi2301Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?bi2301&file=bi2301sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?bi2301sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?bi2301&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [BI2301](http://scripts.iucr.org/cgi-bin/sendsup?bi2301)).

Comment
=======

Benzothiazole derivatives that contain five-membered sulfur-containing heterocyclic rings have been drawing great attention due to their antimalarial and antitumor properties (Alfred & Sawhney, 1968; Hutchinson & Jennings, 2002). Our research group is trying to prepare some benzothiazoles to find new antitumor compounds. In this context, we have crystallized the title compound and report its crystal structure.

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

All reagents and solvents were used as obtained without further purification. 4-Aminobenzoic acid (13.7 g, 0.1 mol) and 2-aminothiophenol (12.5 g, 0.1 mmol) were mixed together with polyphosphoric acid (50 g) and heated to 493 K under an N~2~ atmosphere for 4 h. The reaction mixture was cooled to room temperature and poured into 10% K~2~CO~3~(aq) solution. The precipitate was filtered under reduced pressure. Yellow crystals were obtained by recrystallization from methanol. Yield: 90%. Elemental analysis calculated: C 69.03, H 4.42, N 12.39 %; found: C 69.01, H 4.48, N 12.41 %.

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

All H atoms bound to C atoms were placed in geometrical positions with C---H = 0.93 Å and the *U*~iso~ values were constrained to be 1.2 times *U*~eq~ of the carrier atoms. Atoms H1A, H1B, H4A and H4B were located in difference Foruier maps and refined with N---H restrained to 0.86 (2) Å and with *U*~iso~(H) = 1.2*U*~eq~(N).

Figures
=======

![Molecular structure of the two independent molecules in the title compound. Displacement ellipsoids are drawn at the 50% probability level for non-H atoms.](e-64-o2065-fig1){#Fap1}

![Packing diagram showing molecules linked by N---H···N hydrogen bonds (dashed lines) into layers in the (001) planes.](e-64-o2065-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~13~H~10~N~2~S           *Z* = 4
  *M~r~* = 226.29           *F*(000) = 472
  Triclinic, *P*1           *D*~x~ = 1.386 Mg m^−3^
  Hall symbol: -P 1         Mo *K*α radiation, λ = 0.71073 Å
  *a* = 8.7038 (5) Å        Cell parameters from 2375 reflections
  *b* = 9.5933 (6) Å        θ = 2.3--26.3°
  *c* = 14.5144 (9) Å       µ = 0.27 mm^−1^
  α = 70.720 (1)°           *T* = 298 K
  β = 77.326 (1)°           Block, blue
  γ = 73.170 (1)°           0.30 × 0.20 × 0.20 mm
  *V* = 1084.63 (11) Å^3^   
  ------------------------- ---------------------------------------

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

  ------------------------------------------------------------- --------------------------------------
  Bruker SMART CCD diffractometer                               4199 independent reflections
  Radiation source: fine-focus sealed tube                      3123 reflections with *I* \> 2σ(*I*)
  graphite                                                      *R*~int~ = 0.036
  φ and ω scans                                                 θ~max~ = 26.0°, θ~min~ = 1.5°
  Absorption correction: multi-scan (SADABS; Sheldrick, 2003)   *h* = −10→10
  *T*~min~ = 0.924, *T*~max~ = 0.948                            *k* = −11→10
  6984 measured reflections                                     *l* = −17→15
  ------------------------------------------------------------- --------------------------------------

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^) = 0.115                  H atoms treated by a mixture of independent and constrained refinement
  *S* = 0.97                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0596*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  4199 reflections                      (Δ/σ)~max~ = 0.001
  301 parameters                        Δρ~max~ = 0.29 e Å^−3^
  4 restraints                          Δρ~min~ = −0.23 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    0.1360 (2)     0.6101 (2)     0.06950 (16)    0.0440 (5)           
  C2    0.0112 (3)     0.7409 (3)     0.05957 (19)    0.0611 (7)           
  H2    −0.0368        0.7833         0.0022          0.073\*              
  C3    −0.0402 (3)    0.8066 (3)     0.1348 (2)      0.0679 (7)           
  H3    −0.1234        0.8943         0.1282          0.081\*              
  C4    0.0296 (3)     0.7447 (3)     0.2208 (2)      0.0634 (7)           
  H4    −0.0078        0.7912         0.2711          0.076\*              
  C5    0.1539 (3)     0.6151 (3)     0.23330 (18)    0.0558 (6)           
  H5    0.2007         0.5736         0.2911          0.067\*              
  C6    0.2066 (2)     0.5488 (2)     0.15651 (15)    0.0427 (5)           
  C7    0.3187 (2)     0.4164 (2)     0.02866 (14)    0.0380 (5)           
  C8    0.4141 (2)     0.3129 (2)     −0.02870 (14)   0.0372 (5)           
  C9    0.3726 (2)     0.3255 (2)     −0.11916 (15)   0.0449 (5)           
  H9    0.2833         0.4002         −0.1424         0.054\*              
  C10   0.4606 (3)     0.2302 (2)     −0.17460 (15)   0.0451 (5)           
  H10   0.4295         0.2408         −0.2344         0.054\*              
  C11   0.5958 (2)     0.1178 (2)     −0.14273 (15)   0.0390 (5)           
  C12   0.6382 (2)     0.1045 (2)     −0.05262 (16)   0.0452 (5)           
  H12   0.7282         0.0304         −0.0297         0.054\*              
  C13   0.5487 (2)     0.1994 (2)     0.00275 (15)    0.0427 (5)           
  H13   0.5788         0.1876         0.0630          0.051\*              
  C14   0.6126 (2)     0.2440 (2)     0.53255 (15)    0.0429 (5)           
  C15   0.7512 (3)     0.2790 (3)     0.54271 (18)    0.0551 (6)           
  H15   0.8010         0.2299         0.5992          0.066\*              
  C16   0.8130 (3)     0.3879 (3)     0.4673 (2)      0.0613 (7)           
  H16   0.9060         0.4119         0.4731          0.074\*              
  C17   0.7399 (3)     0.4625 (3)     0.3830 (2)      0.0638 (7)           
  H17   0.7843         0.5357         0.3332          0.077\*              
  C18   0.6027 (3)     0.4301 (3)     0.37176 (18)    0.0601 (7)           
  H18   0.5535         0.4800         0.3151          0.072\*              
  C19   0.5396 (3)     0.3201 (2)     0.44794 (16)    0.0461 (5)           
  C20   0.4087 (2)     0.1299 (2)     0.57195 (14)    0.0386 (5)           
  C21   0.3035 (2)     0.0279 (2)     0.62886 (14)    0.0386 (5)           
  C22   0.3356 (3)     −0.0669 (2)    0.72208 (15)    0.0467 (5)           
  H22   0.4236         −0.0635        0.7472          0.056\*              
  C23   0.2405 (2)     −0.1649 (2)    0.77762 (16)    0.0483 (5)           
  H23   0.2650         −0.2269        0.8396          0.058\*              
  C24   0.1078 (2)     −0.1729 (2)    0.74244 (16)    0.0440 (5)           
  C25   0.0748 (3)     −0.0791 (2)    0.64972 (16)    0.0487 (5)           
  H25   −0.0134        −0.0824        0.6248          0.058\*              
  C26   0.1713 (3)     0.0188 (2)     0.59423 (16)    0.0464 (5)           
  H26   0.1472         0.0802         0.5321          0.056\*              
  N1    0.6820 (2)     0.0234 (2)     −0.19862 (15)   0.0554 (5)           
  N2    0.20084 (19)   0.53292 (18)   −0.00148 (12)   0.0436 (4)           
  N3    0.5371 (2)     0.13608 (18)   0.60184 (12)    0.0433 (4)           
  N4    0.0104 (3)     −0.2687 (3)    0.80188 (16)    0.0600 (6)           
  S1    0.35999 (7)    0.39025 (6)    0.14764 (4)     0.04624 (18)         
  S2    0.36992 (7)    0.25484 (6)    0.45569 (4)     0.05063 (19)         
  H1A   0.655 (3)      0.035 (3)      −0.2540 (13)    0.061\*              
  H1B   0.754 (2)      −0.048 (2)     −0.1747 (16)    0.061\*              
  H4A   −0.038 (3)     −0.292 (3)     0.7646 (15)     0.061\*              
  H4B   0.052 (3)      −0.339 (2)     0.8488 (15)     0.061\*              
  ----- -------------- -------------- --------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  C1    0.0389 (12)   0.0461 (12)   0.0501 (14)   −0.0118 (10)   0.0011 (10)    −0.0207 (10)
  C2    0.0518 (14)   0.0641 (15)   0.0686 (17)   0.0027 (12)    −0.0137 (12)   −0.0309 (13)
  C3    0.0492 (14)   0.0746 (18)   0.086 (2)     0.0000 (13)    −0.0046 (14)   −0.0468 (16)
  C4    0.0532 (15)   0.0781 (17)   0.0731 (18)   −0.0155 (13)   0.0060 (13)    −0.0494 (15)
  C5    0.0573 (15)   0.0649 (15)   0.0536 (15)   −0.0189 (12)   −0.0015 (12)   −0.0279 (12)
  C6    0.0395 (12)   0.0474 (12)   0.0452 (13)   −0.0169 (10)   0.0010 (10)    −0.0170 (10)
  C7    0.0390 (11)   0.0404 (11)   0.0366 (11)   −0.0167 (9)    −0.0025 (9)    −0.0089 (9)
  C8    0.0369 (11)   0.0370 (11)   0.0377 (11)   −0.0124 (9)    −0.0014 (9)    −0.0101 (9)
  C9    0.0441 (12)   0.0447 (12)   0.0411 (12)   −0.0027 (10)   −0.0088 (10)   −0.0110 (10)
  C10   0.0524 (13)   0.0480 (12)   0.0342 (12)   −0.0072 (10)   −0.0096 (10)   −0.0127 (10)
  C11   0.0380 (11)   0.0385 (11)   0.0412 (12)   −0.0124 (9)    0.0004 (9)     −0.0128 (9)
  C12   0.0408 (12)   0.0438 (11)   0.0485 (13)   −0.0029 (9)    −0.0113 (10)   −0.0130 (10)
  C13   0.0450 (12)   0.0459 (12)   0.0395 (12)   −0.0110 (10)   −0.0099 (10)   −0.0123 (10)
  C14   0.0477 (12)   0.0369 (11)   0.0430 (13)   −0.0072 (10)   −0.0016 (10)   −0.0154 (10)
  C15   0.0570 (14)   0.0537 (14)   0.0592 (15)   −0.0143 (12)   −0.0062 (12)   −0.0222 (12)
  C16   0.0586 (15)   0.0556 (14)   0.0763 (19)   −0.0214 (12)   0.0015 (14)    −0.0275 (14)
  C17   0.0738 (18)   0.0478 (14)   0.0643 (17)   −0.0206 (13)   0.0050 (14)    −0.0128 (12)
  C18   0.0688 (17)   0.0495 (14)   0.0535 (15)   −0.0147 (12)   −0.0028 (13)   −0.0066 (12)
  C19   0.0495 (13)   0.0382 (11)   0.0469 (13)   −0.0054 (10)   −0.0010 (10)   −0.0152 (10)
  C20   0.0432 (12)   0.0385 (11)   0.0330 (11)   −0.0027 (9)    −0.0038 (9)    −0.0155 (9)
  C21   0.0401 (11)   0.0398 (11)   0.0358 (11)   −0.0049 (9)    −0.0019 (9)    −0.0167 (9)
  C22   0.0422 (12)   0.0530 (13)   0.0462 (13)   −0.0136 (10)   −0.0106 (10)   −0.0108 (10)
  C23   0.0478 (13)   0.0527 (13)   0.0420 (13)   −0.0140 (10)   −0.0092 (10)   −0.0064 (10)
  C24   0.0391 (12)   0.0446 (12)   0.0490 (13)   −0.0067 (10)   −0.0006 (10)   −0.0203 (10)
  C25   0.0426 (12)   0.0585 (14)   0.0534 (14)   −0.0124 (10)   −0.0099 (11)   −0.0243 (11)
  C26   0.0494 (13)   0.0520 (13)   0.0379 (12)   −0.0059 (10)   −0.0100 (10)   −0.0156 (10)
  N1    0.0568 (13)   0.0576 (12)   0.0497 (13)   0.0022 (10)    −0.0113 (10)   −0.0237 (11)
  N2    0.0417 (10)   0.0446 (10)   0.0435 (10)   −0.0072 (8)    −0.0050 (8)    −0.0145 (8)
  N3    0.0491 (11)   0.0456 (10)   0.0366 (10)   −0.0102 (8)    −0.0058 (8)    −0.0143 (8)
  N4    0.0548 (13)   0.0675 (14)   0.0621 (15)   −0.0266 (11)   −0.0061 (11)   −0.0147 (11)
  S1    0.0501 (3)    0.0474 (3)    0.0425 (3)    −0.0087 (3)    −0.0085 (3)    −0.0156 (2)
  S2    0.0553 (4)    0.0491 (3)    0.0427 (3)    −0.0094 (3)    −0.0117 (3)    −0.0062 (3)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

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

  ----------------------- -------------- ----------------------- --------------
  C1---N2                 1.391 (3)      C15---C16               1.375 (3)
  C1---C2                 1.391 (3)      C15---H15               0.930
  C1---C6                 1.399 (3)      C16---C17               1.384 (3)
  C2---C3                 1.367 (3)      C16---H16               0.930
  C2---H2                 0.930          C17---C18               1.372 (3)
  C3---C4                 1.383 (3)      C17---H17               0.930
  C3---H3                 0.930          C18---C19               1.392 (3)
  C4---C5                 1.380 (3)      C18---H18               0.930
  C4---H4                 0.930          C19---S2                1.732 (2)
  C5---C6                 1.390 (3)      C20---N3                1.307 (2)
  C5---H5                 0.930          C20---C21               1.460 (3)
  C6---S1                 1.730 (2)      C20---S2                1.7543 (19)
  C7---N2                 1.305 (2)      C21---C26               1.388 (3)
  C7---C8                 1.461 (3)      C21---C22               1.393 (3)
  C7---S1                 1.763 (2)      C22---C23               1.370 (3)
  C8---C13                1.390 (3)      C22---H22               0.930
  C8---C9                 1.395 (3)      C23---C24               1.392 (3)
  C9---C10                1.371 (3)      C23---H23               0.930
  C9---H9                 0.930          C24---N4                1.383 (3)
  C10---C11               1.391 (3)      C24---C25               1.387 (3)
  C10---H10               0.930          C25---C26               1.377 (3)
  C11---N1                1.366 (3)      C25---H25               0.930
  C11---C12               1.392 (3)      C26---H26               0.930
  C12---C13               1.371 (3)      N1---H1B                0.819 (15)
  C12---H12               0.930          N1---H1A                0.850 (15)
  C13---H13               0.930          N4---H4A                0.869 (15)
  C14---C19               1.388 (3)      N4---H4B                0.844 (15)
  C14---N3                1.390 (3)      S1---S2                 4.2373 (8)
  C14---C15               1.391 (3)                              
                                                                 
  N2---C1---C2            125.4 (2)      C15---C16---H16         119.3
  N2---C1---C6            115.50 (18)    C17---C16---H16         119.3
  C2---C1---C6            119.1 (2)      C18---C17---C16         121.0 (2)
  C3---C2---C1            119.5 (2)      C18---C17---H17         119.5
  C3---C2---H2            120.3          C16---C17---H17         119.5
  C1---C2---H2            120.3          C17---C18---C19         117.8 (2)
  C2---C3---C4            121.0 (2)      C17---C18---H18         121.1
  C2---C3---H3            119.5          C19---C18---H18         121.1
  C4---C3---H3            119.5          C14---C19---C18         121.6 (2)
  C5---C4---C3            121.3 (2)      C14---C19---S2          109.70 (16)
  C5---C4---H4            119.4          C18---C19---S2          128.71 (19)
  C3---C4---H4            119.4          N3---C20---C21          123.87 (18)
  C4---C5---C6            117.7 (2)      N3---C20---S2           114.84 (15)
  C4---C5---H5            121.1          C21---C20---S2          121.30 (15)
  C6---C5---H5            121.1          C26---C21---C22         117.29 (19)
  C5---C6---C1            121.5 (2)      C26---C21---C20         123.02 (18)
  C5---C6---S1            129.30 (18)    C22---C21---C20         119.69 (18)
  C1---C6---S1            109.24 (16)    C23---C22---C21         121.5 (2)
  N2---C7---C8            124.89 (18)    C23---C22---H22         119.2
  N2---C7---S1            114.76 (15)    C21---C22---H22         119.2
  C8---C7---S1            120.34 (14)    C22---C23---C24         120.8 (2)
  C13---C8---C9           117.06 (19)    C22---C23---H23         119.6
  C13---C8---C7           122.61 (18)    C24---C23---H23         119.6
  C9---C8---C7            120.33 (17)    N4---C24---C25          122.4 (2)
  C10---C9---C8           121.48 (18)    N4---C24---C23          119.4 (2)
  C10---C9---H9           119.3          C25---C24---C23         118.1 (2)
  C8---C9---H9            119.3          C26---C25---C24         120.7 (2)
  C9---C10---C11          120.95 (19)    C26---C25---H25         119.7
  C9---C10---H10          119.5          C24---C25---H25         119.7
  C11---C10---H10         119.5          C25---C26---C21         121.5 (2)
  N1---C11---C10          120.28 (19)    C25---C26---H26         119.2
  N1---C11---C12          121.75 (18)    C21---C26---H26         119.2
  C10---C11---C12         117.97 (19)    C11---N1---H1B          117.7 (17)
  C13---C12---C11         120.69 (19)    C11---N1---H1A          120.2 (16)
  C13---C12---H12         119.7          H1B---N1---H1A          122 (2)
  C11---C12---H12         119.7          C7---N2---C1            110.94 (17)
  C12---C13---C8          121.86 (19)    C20---N3---C14          110.98 (17)
  C12---C13---H13         119.1          C24---N4---H4A          108.7 (16)
  C8---C13---H13          119.1          C24---N4---H4B          116.1 (17)
  C19---C14---N3          115.20 (19)    H4A---N4---H4B          118 (2)
  C19---C14---C15         119.69 (19)    C6---S1---C7            89.56 (10)
  N3---C14---C15          125.1 (2)      C6---S1---S2            90.73 (7)
  C16---C15---C14         118.5 (2)      C7---S1---S2            164.85 (6)
  C16---C15---H15         120.8          C19---S2---C20          89.27 (10)
  C14---C15---H15         120.8          C19---S2---S1           95.40 (7)
  C15---C16---C17         121.4 (2)      C20---S2---S1           157.02 (7)
                                                                 
  N2---C1---C2---C3       −179.3 (2)     S2---C20---C21---C22    −178.30 (15)
  C6---C1---C2---C3       −0.2 (3)       C26---C21---C22---C23   −0.2 (3)
  C1---C2---C3---C4       −0.2 (4)       C20---C21---C22---C23   −179.62 (19)
  C2---C3---C4---C5       0.3 (4)        C21---C22---C23---C24   0.0 (3)
  C3---C4---C5---C6       0.0 (4)        C22---C23---C24---N4    −177.5 (2)
  C4---C5---C6---C1       −0.4 (3)       C22---C23---C24---C25   0.1 (3)
  C4---C5---C6---S1       178.68 (17)    N4---C24---C25---C26    177.6 (2)
  N2---C1---C6---C5       179.73 (18)    C23---C24---C25---C26   0.1 (3)
  C2---C1---C6---C5       0.5 (3)        C24---C25---C26---C21   −0.4 (3)
  N2---C1---C6---S1       0.5 (2)        C22---C21---C26---C25   0.4 (3)
  C2---C1---C6---S1       −178.76 (17)   C20---C21---C26---C25   179.80 (19)
  N2---C7---C8---C13      173.49 (18)    C8---C7---N2---C1       −179.01 (17)
  S1---C7---C8---C13      −5.9 (3)       S1---C7---N2---C1       0.4 (2)
  N2---C7---C8---C9       −6.2 (3)       C2---C1---N2---C7       178.6 (2)
  S1---C7---C8---C9       174.43 (15)    C6---C1---N2---C7       −0.6 (3)
  C13---C8---C9---C10     0.0 (3)        C21---C20---N3---C14    −179.77 (17)
  C7---C8---C9---C10      179.73 (18)    S2---C20---N3---C14     0.5 (2)
  C8---C9---C10---C11     −0.5 (3)       C19---C14---N3---C20    −0.5 (3)
  C9---C10---C11---N1     179.81 (19)    C15---C14---N3---C20    179.33 (19)
  C9---C10---C11---C12    0.4 (3)        C5---C6---S1---C7       −179.4 (2)
  N1---C11---C12---C13    −179.2 (2)     C1---C6---S1---C7       −0.23 (15)
  C10---C11---C12---C13   0.2 (3)        C5---C6---S1---S2       15.8 (2)
  C11---C12---C13---C8    −0.7 (3)       C1---C6---S1---S2       −165.07 (14)
  C9---C8---C13---C12     0.6 (3)        N2---C7---S1---C6       −0.08 (15)
  C7---C8---C13---C12     −179.14 (18)   C8---C7---S1---C6       179.33 (16)
  C19---C14---C15---C16   −0.7 (3)       N2---C7---S1---S2       91.1 (3)
  N3---C14---C15---C16    179.4 (2)      C8---C7---S1---S2       −89.5 (3)
  C14---C15---C16---C17   0.4 (3)        C14---C19---S2---C20    0.00 (15)
  C15---C16---C17---C18   −0.1 (4)       C18---C19---S2---C20    179.6 (2)
  C16---C17---C18---C19   0.1 (4)        C14---C19---S2---S1     −157.47 (14)
  N3---C14---C19---C18    −179.35 (19)   C18---C19---S2---S1     22.1 (2)
  C15---C14---C19---C18   0.8 (3)        N3---C20---S2---C19     −0.31 (16)
  N3---C14---C19---S2     0.3 (2)        C21---C20---S2---C19    179.97 (17)
  C15---C14---C19---S2    −179.57 (16)   N3---C20---S2---S1      101.9 (2)
  C17---C18---C19---C14   −0.5 (3)       C21---C20---S2---S1     −77.8 (2)
  C17---C18---C19---S2    179.95 (18)    C6---S1---S2---C19      −101.16 (9)
  N3---C20---C21---C26    −177.40 (18)   C7---S1---S2---C19      167.8 (3)
  S2---C20---C21---C26    2.3 (3)        C6---S1---S2---C20      157.87 (19)
  N3---C20---C21---C22    2.0 (3)        C7---S1---S2---C20      66.9 (3)
  ----------------------- -------------- ----------------------- --------------

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

  ------------------- ---------- ---------- ----------- ---------------
  *D*---H···*A*       *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  N1---H1B···N4^i^    0.82 (2)   2.64 (2)   3.374 (3)   149 (2)
  N1---H1A···N3^ii^   0.85 (2)   2.32 (2)   3.145 (3)   163 (2)
  ------------------- ---------- ---------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*         *D*---H      H⋯*A*        *D*⋯*A*     *D*---H⋯*A*
  ------------------- ------------ ------------ ----------- -------------
  N1---H1*B*⋯N4^i^    0.819 (15)   2.644 (18)   3.374 (3)   149 (2)
  N1---H1*A*⋯N3^ii^   0.850 (15)   2.324 (16)   3.145 (3)   163 (2)

Symmetry codes: (i) ; (ii) .
