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

For the toxicity and insecticidal activity of the title compound, see: Altuntas *et al.* ( 2002[@bb1]).  For related structures, see: Rohrbaugh *et al.* ( 1976[@bb4]). 

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~6~H~11~N~2~O~4~PS~3~*M* *~r~* = 302.32Monoclinic,*a* = 12.3944 (2) Å*b* = 10.8056 (1) Å*c* = 19.3631 (3) Åβ = 102.815 (1)°*V* = 2528.68 (6) Å^3^*Z* = 8Mo *K*α radiationμ = 0.71 mm^−1^*T* = 173 K0.30 × 0.27 × 0.19 mm

### Data collection {#sec2.1.2}

Bruker APEXII CCD diffractometerAbsorption correction: multi-scan (*SADABS*; Sheldrick, 1996[@bb5]) *T* ~min~ = 0.815, *T* ~max~ = 0.87720918 measured reflections5513 independent reflections4682 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.024

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.033*wR*(*F* ^2^) = 0.089*S* = 1.075513 reflections289 parametersH-atom parameters constrainedΔρ~max~ = 0.98 e Å^−3^Δρ~min~ = −0.55 e Å^−3^

 {#d5e547}

Data collection: *APEX2* (Bruker, 2006[@bb3]); cell refinement: *SAINT* (Bruker, 2006[@bb3]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXTL* (Sheldrick, 2008[@bb6]); program(s) used to refine structure: *SHELXTL*; molecular graphics: *SHELXTL* and *DIAMOND* (Brandenburg, 1998[@bb2]); software used to prepare material for publication: *SHELXTL*. 

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536811005241/jh2268sup1.cif](http://dx.doi.org/10.1107/S1600536811005241/jh2268sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536811005241/jh2268Isup2.hkl](http://dx.doi.org/10.1107/S1600536811005241/jh2268Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?jh2268&file=jh2268sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?jh2268sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?jh2268&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [JH2268](http://scripts.iucr.org/cgi-bin/sendsup?jh2268)). 

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No.  2010--0009089). 

Comment
=======

Methidathion (systematic name: *S*-2,3-dihydro-5-methoxy-2-oxo-1,3,4- thiadiazol-3-ylmethyl *O*,*O*-dimethyl phosphorodithioate), is one of the most widely used organophosphate insecticides in agriculture and public health programmes (Altuntas *et al.*  2002).  However it\'s crystal structure has not been reported yet. 

In the title compound (Scheme 1, Fig.  1), crystallizes with two independent molecules in the asymmetric unit.  The dihedral angles between the thiadiazol ring planes and the PS~2~ planes of the phosphorodithioate group are 86.51 (5)° and 56.33 (5)° in the two molecules.  All bond lengths and bond angles are normal and comparable to those observed in similar structures (Rohrbaugh *et al.*  1976). 

In the crystal structure, as shown in Fig.  2, weak intermolecular C---H···O, C---H···N hydrogen bonds (Table 1) and S···S interactions with 3.3372 (8) Å are observed (Table 1).  These intermolecular interactions may be contribute to the stabilization of the packing. 

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

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company.  Slow evaporation of a solution in CH~2~Cl~2~ gave single crystals suitable for X-ray analysis. 

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

All H-atoms were positioned geometrically and refined using a riding model with d(C---H) = 0.99 Å, *U*~iso~ = 1.2*U*~eq~(C) for CH~2~ and d(C---H) = 0.98 Å, *U*~iso~ = 1.5*U*~eq~(C) for CH~3~ groups. 

Figures
=======

![ The molecular structure of the title compound with the atom numbering scheme.  Displacement ellipsoids are drawn at the 50% probability level.  H atoms are presented as a small spheres of arbitrary radius.](e-67-0o653-fig1){#Fap1}

![ Crystal packing of the title compound with intermolecular C---H···O, C---H···N hydrogen bonds and S···S interactions shown as dashed lines.  H atoms not involved in intermolecular interactions have been omitted for clarity.  \[Symmetry codes: (i) -x, -y, -z; (ii) x + 1, y, z; (iii) -x + 1, -y, -z; (iv) -x + 1, -y + 1, -z; (v) -x, -y + 1, -z.\]](e-67-0o653-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~6~H~11~N~2~O~4~PS~3~    *F*(000) = 1248
  *M~r~* = 302.32           *D*~x~ = 1.588 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ybc      Cell parameters from 9930 reflections
  *a* = 12.3944 (2) Å       θ = 2.5--28.2°
  *b* = 10.8056 (1) Å       µ = 0.71 mm^−1^
  *c* = 19.3631 (3) Å       *T* = 173 K
  β = 102.815 (1)°          Block, colourless
  *V* = 2528.68 (6) Å^3^    0.30 × 0.27 × 0.19 mm
  *Z* = 8                   
  ------------------------- ---------------------------------------

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

  --------------------------------------------------------------- --------------------------------------
  Bruker APEXII CCD diffractometer                                5513 independent reflections
  Radiation source: fine-focus sealed tube                        4682 reflections with *I* \> 2σ(*I*)
  graphite                                                        *R*~int~ = 0.024
  φ and ω scans                                                   θ~max~ = 27.0°, θ~min~ = 1.7°
  Absorption correction: multi-scan (*SADABS*; Sheldrick, 1996)   *h* = −15→11
  *T*~min~ = 0.815, *T*~max~ = 0.877                              *k* = −11→13
  20918 measured reflections                                      *l* = −24→24
  --------------------------------------------------------------- --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.033   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.089                  H-atom parameters constrained
  *S* = 1.07                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0424*P*)^2^ + 1.2139*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  5513 reflections                      (Δ/σ)~max~ = 0.001
  289 parameters                        Δρ~max~ = 0.98 e Å^−3^
  0 restraints                          Δρ~min~ = −0.55 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~   
  P1     0.02509 (4)     0.14885 (4)     0.16800 (3)    0.02754 (12)         
  P2     0.60901 (4)     −0.02370 (5)    0.25072 (3)    0.02917 (13)         
  S1     0.01168 (5)     0.17732 (6)     0.26343 (3)    0.04165 (15)         
  S2     0.15513 (4)     0.02823 (5)     0.16946 (3)    0.03550 (14)         
  S3     0.16030 (4)     −0.35504 (4)    0.03186 (3)    0.03270 (13)         
  S4     0.57301 (6)     −0.06480 (7)    0.33906 (3)    0.05122 (17)         
  S5     0.46376 (4)     0.01769 (5)     0.17901 (3)    0.03259 (13)         
  S6     0.48755 (4)     0.34626 (5)     −0.00393 (3)   0.03301 (13)         
  O1     −0.07804 (11)   0.09769 (14)    0.11286 (7)    0.0355 (3)           
  O2     0.04167 (15)    0.26370 (13)    0.12160 (8)    0.0459 (4)           
  O3     0.31042 (11)    −0.17257 (13)   0.05006 (8)    0.0363 (3)           
  O4     −0.05059 (11)   −0.37521 (12)   0.03211 (8)    0.0338 (3)           
  O5     0.69519 (11)    0.08288 (13)    0.25149 (7)    0.0326 (3)           
  O6     0.67189 (12)    −0.12180 (13)   0.21387 (8)    0.0347 (3)           
  O7     0.35232 (12)    0.15068 (14)    −0.01300 (8)   0.0412 (4)           
  O8     0.67746 (11)    0.41371 (13)    0.07718 (8)    0.0351 (3)           
  N1     0.13193 (12)    −0.12835 (14)   0.05709 (8)    0.0243 (3)           
  N2     0.02836 (13)    −0.18037 (14)   0.05340 (9)    0.0263 (3)           
  N3     0.51734 (13)    0.14990 (15)    0.06949 (9)    0.0283 (4)           
  N4     0.60999 (13)    0.22068 (15)    0.09789 (8)    0.0269 (3)           
  C1     −0.14361 (19)   −0.0019 (2)     0.13290 (14)   0.0459 (6)           
  H1A    −0.2042         −0.0227         0.0927         0.069\*              
  H1B    −0.1742         0.0246          0.1730         0.069\*              
  H1C    −0.0967         −0.0748         0.1465         0.069\*              
  C2     0.1050 (3)      0.3680 (3)      0.14990 (15)   0.0700 (9)           
  H2A    0.1047          0.4285          0.1122         0.105\*              
  H2B    0.1813          0.3423          0.1703         0.105\*              
  H2C    0.0731          0.4055          0.1869         0.105\*              
  C3     0.14752 (16)    0.00052 (17)    0.07483 (10)   0.0273 (4)           
  H3A    0.0853          0.0487          0.0464         0.033\*              
  H3B    0.2167          0.0298          0.0626         0.033\*              
  C4     0.21602 (15)    −0.20269 (17)   0.04761 (10)   0.0259 (4)           
  C5     0.03364 (15)    −0.29610 (17)   0.04052 (10)   0.0263 (4)           
  C6     −0.15623 (17)   −0.31980 (19)   0.03375 (14)   0.0383 (5)           
  H6A    −0.2133         −0.3842         0.0272         0.057\*              
  H6B    −0.1755         −0.2586         −0.0043        0.057\*              
  H6C    −0.1515         −0.2791         0.0795         0.057\*              
  C7     0.6764 (2)      0.2031 (2)      0.27938 (12)   0.0426 (5)           
  H7A    0.7376          0.2585          0.2760         0.064\*              
  H7B    0.6721          0.1949          0.3291         0.064\*              
  H7C    0.6069          0.2375          0.2520         0.064\*              
  C8     0.6314 (2)      −0.2470 (2)     0.20117 (15)   0.0536 (7)           
  H8A    0.6811          −0.2940         0.1780         0.080\*              
  H8B    0.5570          −0.2456         0.1705         0.080\*              
  H8C    0.6287          −0.2864         0.2464         0.080\*              
  C9     0.50949 (17)    0.02671 (18)    0.09544 (10)   0.0291 (4)           
  H9A    0.5829          −0.0133         0.1020         0.035\*              
  H9B    0.4572          −0.0210         0.0591         0.035\*              
  C10    0.43898 (16)    0.19916 (19)    0.01633 (11)   0.0305 (4)           
  C11    0.60347 (16)    0.32287 (18)    0.06415 (10)   0.0275 (4)           
  C12    0.7657 (2)      0.3958 (2)      0.13932 (13)   0.0494 (6)           
  H12A   0.8163          0.4666          0.1448         0.074\*              
  H12B   0.8063          0.3199          0.1339         0.074\*              
  H12C   0.7342          0.3887          0.1813         0.074\*              
  ------ --------------- --------------- -------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  P1    0.0317 (3)    0.0231 (2)    0.0290 (3)    0.00059 (19)   0.0094 (2)     −0.0009 (2)
  P2    0.0291 (3)    0.0324 (3)    0.0282 (3)    −0.0032 (2)    0.0112 (2)     0.0027 (2)
  S1    0.0511 (4)    0.0445 (3)    0.0318 (3)    −0.0008 (3)    0.0143 (3)     −0.0075 (2)
  S2    0.0322 (3)    0.0394 (3)    0.0307 (3)    0.0102 (2)     −0.0021 (2)    −0.0081 (2)
  S3    0.0272 (3)    0.0230 (2)    0.0480 (3)    0.00344 (19)   0.0086 (2)     −0.0059 (2)
  S4    0.0610 (4)    0.0630 (4)    0.0361 (3)    −0.0113 (3)    0.0247 (3)     0.0075 (3)
  S5    0.0229 (2)    0.0389 (3)    0.0378 (3)    −0.0022 (2)    0.0106 (2)     −0.0046 (2)
  S6    0.0327 (3)    0.0342 (3)    0.0299 (3)    0.0100 (2)     0.0021 (2)     0.0020 (2)
  O1    0.0268 (7)    0.0473 (9)    0.0317 (8)    0.0021 (6)     0.0051 (6)     0.0004 (7)
  O2    0.0710 (11)   0.0257 (7)    0.0442 (9)    −0.0051 (7)    0.0200 (8)     0.0005 (7)
  O3    0.0253 (7)    0.0347 (8)    0.0505 (9)    −0.0015 (6)    0.0119 (7)     −0.0092 (7)
  O4    0.0269 (7)    0.0220 (6)    0.0529 (9)    −0.0008 (5)    0.0098 (7)     −0.0015 (6)
  O5    0.0290 (7)    0.0361 (8)    0.0335 (8)    −0.0074 (6)    0.0089 (6)     −0.0008 (6)
  O6    0.0360 (8)    0.0310 (7)    0.0394 (8)    0.0035 (6)     0.0131 (7)     0.0057 (6)
  O7    0.0283 (8)    0.0419 (9)    0.0463 (9)    0.0062 (7)     −0.0068 (7)    −0.0131 (7)
  O8    0.0297 (7)    0.0351 (8)    0.0396 (8)    −0.0035 (6)    0.0054 (6)     0.0071 (7)
  N1    0.0219 (8)    0.0211 (7)    0.0304 (8)    −0.0001 (6)    0.0067 (7)     −0.0015 (6)
  N2    0.0240 (8)    0.0231 (8)    0.0321 (9)    −0.0004 (6)    0.0071 (7)     −0.0003 (7)
  N3    0.0264 (8)    0.0274 (8)    0.0283 (9)    0.0007 (6)     0.0002 (7)     −0.0022 (7)
  N4    0.0238 (8)    0.0301 (8)    0.0262 (8)    0.0000 (6)     0.0041 (7)     −0.0002 (7)
  C1    0.0336 (12)   0.0538 (14)   0.0530 (15)   −0.0132 (10)   0.0157 (11)    −0.0132 (12)
  C2    0.098 (2)     0.0519 (16)   0.0517 (16)   −0.0435 (16)   −0.0026 (16)   0.0031 (13)
  C3    0.0284 (10)   0.0230 (9)    0.0306 (10)   −0.0004 (8)    0.0069 (8)     −0.0014 (8)
  C4    0.0275 (10)   0.0241 (9)    0.0261 (9)    0.0023 (7)     0.0057 (8)     −0.0020 (8)
  C5    0.0256 (10)   0.0239 (9)    0.0292 (10)   0.0028 (7)     0.0056 (8)     0.0007 (8)
  C6    0.0264 (11)   0.0295 (10)   0.0604 (15)   −0.0019 (8)    0.0127 (10)    −0.0041 (10)
  C7    0.0519 (14)   0.0384 (12)   0.0360 (12)   −0.0105 (10)   0.0069 (11)    −0.0075 (10)
  C8    0.0713 (18)   0.0287 (12)   0.0661 (17)   −0.0002 (11)   0.0269 (15)    0.0012 (11)
  C9    0.0292 (10)   0.0279 (10)   0.0300 (10)   0.0007 (8)     0.0065 (8)     −0.0053 (8)
  C10   0.0274 (10)   0.0327 (10)   0.0299 (10)   0.0088 (8)     0.0031 (9)     −0.0074 (8)
  C11   0.0240 (9)    0.0324 (10)   0.0263 (10)   0.0050 (8)     0.0063 (8)     0.0003 (8)
  C12   0.0428 (14)   0.0520 (14)   0.0460 (14)   −0.0172 (11)   −0.0056 (11)   0.0082 (12)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

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

  --------------------- -------------- --------------------- --------------
  P1---O2               1.5720 (15)    N2---C5               1.280 (2)
  P1---O1               1.5730 (15)    N3---C10              1.357 (3)
  P1---S1               1.9166 (7)     N3---N4               1.388 (2)
  P1---S2               2.0681 (7)     N3---C9               1.434 (2)
  P2---O5               1.5685 (14)    N4---C11              1.277 (2)
  P2---O6               1.5770 (15)    C1---H1A              0.9800
  P2---S4               1.9135 (7)     C1---H1B              0.9800
  P2---S5               2.0640 (8)     C1---H1C              0.9800
  S2---C3               1.838 (2)      C2---H2A              0.9800
  S3---C5               1.7363 (19)    C2---H2B              0.9800
  S3---C4               1.7852 (19)    C2---H2C              0.9800
  S5---C9               1.832 (2)      C3---H3A              0.9900
  S6---C11              1.739 (2)      C3---H3B              0.9900
  S6---C10              1.774 (2)      C6---H6A              0.9800
  O1---C1               1.452 (3)      C6---H6B              0.9800
  O2---C2               1.413 (3)      C6---H6C              0.9800
  O3---C4               1.205 (2)      C7---H7A              0.9800
  O4---C5               1.331 (2)      C7---H7B              0.9800
  O4---C6               1.446 (2)      C7---H7C              0.9800
  O5---C7               1.446 (3)      C8---H8A              0.9800
  O6---C8               1.445 (3)      C8---H8B              0.9800
  O7---C10              1.217 (2)      C8---H8C              0.9800
  O8---C11              1.329 (2)      C9---H9A              0.9900
  O8---C12              1.448 (3)      C9---H9B              0.9900
  N1---C4               1.360 (2)      C12---H12A            0.9800
  N1---N2               1.389 (2)      C12---H12B            0.9800
  N1---C3               1.437 (2)      C12---H12C            0.9800
                                                             
  O2---P1---O1          94.54 (9)      N1---C3---H3B         109.3
  O2---P1---S1          118.33 (6)     S2---C3---H3B         109.3
  O1---P1---S1          118.66 (6)     H3A---C3---H3B        107.9
  O2---P1---S2          107.77 (7)     O3---C4---N1          126.98 (18)
  O1---P1---S2          107.54 (6)     O3---C4---S3          126.24 (15)
  S1---P1---S2          108.78 (3)     N1---C4---S3          106.78 (13)
  O5---P2---O6          95.40 (8)      N2---C5---O4          125.36 (17)
  O5---P2---S4          117.08 (6)     N2---C5---S3          117.62 (15)
  O6---P2---S4          119.02 (6)     O4---C5---S3          117.00 (13)
  O5---P2---S5          109.75 (6)     O4---C6---H6A         109.5
  O6---P2---S5          106.63 (6)     O4---C6---H6B         109.5
  S4---P2---S5          108.07 (3)     H6A---C6---H6B        109.5
  C3---S2---P1          102.80 (7)     O4---C6---H6C         109.5
  C5---S3---C4          88.23 (9)      H6A---C6---H6C        109.5
  C9---S5---P2          102.19 (7)     H6B---C6---H6C        109.5
  C11---S6---C10        88.05 (9)      O5---C7---H7A         109.5
  C1---O1---P1          119.85 (14)    O5---C7---H7B         109.5
  C2---O2---P1          122.67 (16)    H7A---C7---H7B        109.5
  C5---O4---C6          114.88 (15)    O5---C7---H7C         109.5
  C7---O5---P2          119.87 (13)    H7A---C7---H7C        109.5
  C8---O6---P2          121.24 (14)    H7B---C7---H7C        109.5
  C11---O8---C12        114.92 (16)    O6---C8---H8A         109.5
  C4---N1---N2          118.77 (15)    O6---C8---H8B         109.5
  C4---N1---C3          122.56 (16)    H8A---C8---H8B        109.5
  N2---N1---C3          118.57 (14)    O6---C8---H8C         109.5
  C5---N2---N1          108.60 (15)    H8A---C8---H8C        109.5
  C10---N3---N4         118.32 (16)    H8B---C8---H8C        109.5
  C10---N3---C9         122.48 (17)    N3---C9---S5          114.67 (13)
  N4---N3---C9          119.16 (16)    N3---C9---H9A         108.6
  C11---N4---N3         108.72 (16)    S5---C9---H9A         108.6
  O1---C1---H1A         109.5          N3---C9---H9B         108.6
  O1---C1---H1B         109.5          S5---C9---H9B         108.6
  H1A---C1---H1B        109.5          H9A---C9---H9B        107.6
  O1---C1---H1C         109.5          O7---C10---N3         126.5 (2)
  H1A---C1---H1C        109.5          O7---C10---S6         126.18 (16)
  H1B---C1---H1C        109.5          N3---C10---S6         107.35 (14)
  O2---C2---H2A         109.5          N4---C11---O8         125.39 (18)
  O2---C2---H2B         109.5          N4---C11---S6         117.48 (15)
  H2A---C2---H2B        109.5          O8---C11---S6         117.12 (14)
  O2---C2---H2C         109.5          O8---C12---H12A       109.5
  H2A---C2---H2C        109.5          O8---C12---H12B       109.5
  H2B---C2---H2C        109.5          H12A---C12---H12B     109.5
  N1---C3---S2          111.76 (13)    O8---C12---H12C       109.5
  N1---C3---H3A         109.3          H12A---C12---H12C     109.5
  S2---C3---H3A         109.3          H12B---C12---H12C     109.5
                                                             
  O2---P1---S2---C3     −55.63 (9)     C3---N1---C4---O3     −2.7 (3)
  O1---P1---S2---C3     45.23 (9)      N2---N1---C4---S3     0.3 (2)
  S1---P1---S2---C3     174.93 (7)     C3---N1---C4---S3     176.58 (14)
  O5---P2---S5---C9     61.04 (9)      C5---S3---C4---O3     179.15 (19)
  O6---P2---S5---C9     −41.17 (9)     C5---S3---C4---N1     −0.10 (14)
  S4---P2---S5---C9     −170.21 (7)    N1---N2---C5---O4     −178.69 (17)
  O2---P1---O1---C1     −169.51 (15)   N1---N2---C5---S3     0.2 (2)
  S1---P1---O1---C1     −43.64 (17)    C6---O4---C5---N2     4.0 (3)
  S2---P1---O1---C1     80.24 (15)     C6---O4---C5---S3     −174.91 (15)
  O1---P1---O2---C2     162.2 (2)      C4---S3---C5---N2     −0.09 (17)
  S1---P1---O2---C2     36.1 (2)       C4---S3---C5---O4     178.94 (16)
  S2---P1---O2---C2     −87.7 (2)      C10---N3---C9---S5    −101.82 (19)
  O6---P2---O5---C7     178.26 (15)    N4---N3---C9---S5     80.34 (19)
  S4---P2---O5---C7     −55.19 (16)    P2---S5---C9---N3     −105.14 (14)
  S5---P2---O5---C7     68.42 (15)     N4---N3---C10---O7    −178.22 (18)
  O5---P2---O6---C8     177.37 (18)    C9---N3---C10---O7    3.9 (3)
  S4---P2---O6---C8     52.25 (19)     N4---N3---C10---S6    3.0 (2)
  S5---P2---O6---C8     −70.14 (18)    C9---N3---C10---S6    −174.84 (14)
  C4---N1---N2---C5     −0.3 (2)       C11---S6---C10---O7   179.08 (19)
  C3---N1---N2---C5     −176.80 (17)   C11---S6---C10---N3   −2.15 (14)
  C10---N3---N4---C11   −2.3 (2)       N3---N4---C11---O8    179.59 (17)
  C9---N3---N4---C11    175.65 (16)    N3---N4---C11---S6    0.3 (2)
  C4---N1---C3---S2     −101.78 (18)   C12---O8---C11---N4   −6.0 (3)
  N2---N1---C3---S2     74.52 (18)     C12---O8---C11---S6   173.21 (16)
  P1---S2---C3---N1     −120.69 (12)   C10---S6---C11---N4   1.10 (16)
  N2---N1---C4---O3     −178.97 (19)   C10---S6---C11---O8   −178.22 (15)
  --------------------- -------------- --------------------- --------------

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

  -------------------- --------- --------- ----------- ---------------
  *D*---H···*A*        *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C1---H1A···O7^i^     0.98      2.53      3.464 (3)   159
  C1---H1B···O5^ii^    0.98      2.53      3.484 (3)   164
  C2---H2B···O6^iii^   0.98      2.59      3.373 (3)   138
  C3---H3A···N2^i^     0.99      2.56      3.506 (3)   161
  C6---H6B···O7^i^     0.98      2.57      2.996 (2)   106
  C9---H9B···O3        0.99      2.42      3.246 (2)   140
  -------------------- --------- --------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*          *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  -------------------- --------- ------- ----------- -------------
  C1---H1*A*⋯O7^i^     0.98      2.53    3.464 (3)   159
  C1---H1*B*⋯O5^ii^    0.98      2.53    3.484 (3)   164
  C2---H2*B*⋯O6^iii^   0.98      2.59    3.373 (3)   138
  C3---H3*A*⋯N2^i^     0.99      2.56    3.506 (3)   161
  C9---H9*B*⋯O3        0.99      2.42    3.246 (2)   140

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