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

For the biological and pharmaceutical properties of compounds containing a fused thienopyrimidine system, see: Amr *et al.* ( 2010[@bb1]); Huang *et al.* ( 2009[@bb4]); Jennings *et al.* ( 2005[@bb5]); Kikuchi *et al.* ( 2006[@bb6]); Mavrova *et al.* ( 2010[@bb7]); Santagati *et al.* ( 2002[@bb8]).  For similar crystal structures, see: Xie *et al.* ( 2008[@bb11]); Chen *et al.* ( 2011[@bb3]). 

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~26~H~27~ClN~4~OS*M* *~r~* = 479.03Monoclinic,*a* = 17.428 (13) Å*b* = 9.391 (7) Å*c* = 16.170 (13) Åβ = 111.995 (7)°*V* = 2454 (3) Å^3^*Z* = 4Mo *K*α radiationμ = 0.27 mm^−1^*T* = 296 K0.26 × 0.24 × 0.20 mm

### Data collection   {#sec2.1.2}

Bruker SMART CCD diffractometerAbsorption correction: multi-scan (*SADABS*; Sheldrick, 1996[@bb9]) *T* ~min~ = 0.934, *T* ~max~ = 0.94925485 measured reflections5611 independent reflections3883 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.090

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.070*wR*(*F* ^2^) = 0.164*S* = 1.065611 reflections300 parametersH-atom parameters constrainedΔρ~max~ = 0.36 e Å^−3^Δρ~min~ = −0.26 e Å^−3^

 {#d5e438}

Data collection: *SMART* (Bruker, 1997[@bb2]); cell refinement: *SAINT* (Bruker, 1997[@bb2]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXTL* (Sheldrick, 2008[@bb10]); program(s) used to refine structure: *SHELXTL*; molecular graphics: *SHELXTL*; software used to prepare material for publication: *SHELXTL*. 

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

Crystal structure: contains datablock(s) I, global.  DOI: [10.1107/S1600536812007246/nc2265sup1.cif](http://dx.doi.org/10.1107/S1600536812007246/nc2265sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536812007246/nc2265Isup2.hkl](http://dx.doi.org/10.1107/S1600536812007246/nc2265Isup2.hkl)

Supplementary material file.  DOI: [10.1107/S1600536812007246/nc2265Isup3.cml](http://dx.doi.org/10.1107/S1600536812007246/nc2265Isup3.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?nc2265&file=nc2265sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?nc2265sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?nc2265&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [NC2265](http://scripts.iucr.org/cgi-bin/sendsup?nc2265)). 

This work was supported financially by the National Natural Science Foundation of China (Project No.  21102084), the Key Project of Hubei Provincial Department of Education (Project No.  D20091301) and the Doctoral Startup Foundation of China Three Gorges University (Project No.  KJ2009B004). 

Comment
=======

Derivatives of heterocycles containing the thienopyrimidine system have proved to show significant antifungal, antibacterical, anticonvulsant and angiotensin antagonistic activities (Amr *et al.*  2010; Huang *et al.*  2009; Jennings *et al.*  2005; Kikuchi *et al.*  2006; Mavrova *et al.*  2010; Santagati *et al.*  2002).  Recently, we have focused on the synthesis of fused heterocyclic systems containing thienopyrimidine *via* aza-wittig reaction under mild conditions.  Some X-ray crystal structures of fused pyrimidinone derivatives have been reported (Chen *et al.*,  2011; Xie *et al.*,  2008).  The title compound has potential use as a precursor for obtaining bioactive molecules with fluorescence properties.  Herein, we report its crystal structure (Fig.  1). 

In the crystal structure of the title compound, C~26~H~27~ClN~4~OS, the thienopyrimidine fused-ring system is close to coplanar (r.m.s deviation = 0.0089 Å) with a maximum deviation of 0.0283 (17) Å for atom N(3).  This ring system forms dihedral angles of 83.51 (3) and 88.20 (5)° with the adjacent 6-membered rings C1--C6 and C17--C22, respectively.  Intermolecular N4---H4···Cl1^i^ interactions, as well as intermolecular hydrogen bonds (C8---H8*B*···O1^ii^), help to stablize the crystal structure (Symmetry codes: (i) -*x* + 1, -*y* + 2, -*z*; (ii) -*x* + 1, -*y* + 2, -*z* + 1) (Table 1). 

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

1-Chloro-4-isocyanatobenzene (2 mmol) under nitrogen atmosphere was added to a solution of iminophosphorane (1.15 g, 2 mmol) in anhydrous dichloromethane (10 ml) at room temperature.  When the reaction mixture was left unstirred for 12 h at 273--278 K, iminophosphorane was consumed (TLC monitored).  The solvent was removed under reduced pressure and ether/petroleum ether (volume ratio 1:2, 20 ml) was added to precipitate triphenylphosphine oxide.  Removal of the solvent gave carbodiimide, which was used directly without further purification. * Iso*-butylamine (2 mmol) was added to the solution of carbodiimide in anhydrous dichloromethane (10 ml).  After the reaction mixture was left unstirred for 5--6 h, the solvent was removed and the residual was recrystallized from ethanol and dichloromethane to give the expected title compound in white crystals.  Yield: 87%, m.p.  461--462 K. IR (KBr) cm^-1^ 3341 (N---H), 1675 (C═O), 1541, 1433, 1223, 691; ^1^H NMR (CDCl~3~, 600 MHz) δ (p.p.m.):  7.55--7.22 (m, 9H, Ar---H), 4.07 (br, 1H, NH), 3.72 (s, 2H, Ar---CH~2~), 3.60 (s, 2H, NCH~2~-thiophene), 3.18 (t, *J* = 6.3 Hz, 2H, NHCH~2~), 2.98 (t, *J* = 5.7 Hz, 2H, NCH~2~CH~2~), 2.83 (t, *J* = 5.7 Hz, 2H, NCH~2~CH~2~), 1.80--1.76 (m, *J* = 5.4 Hz, 1H, CH), 0.83 (s, 6H, 2 CH~3~); EI--MS (*m/z*, %): 480.06 (*M*+2^+^, 17), 478.01 (*M*^+^, 52), 387.02 (14), 358.96 (57), 303.01 (42), 152.03 (21), 91.09 (100), 44.02 (15).  Anal.  Calcd. (%)  for C~26~H~27~ClN~4~OS: C, 65.19; H, 5.68; N, 11.70.  Found (%): C, 65.47; H, 5.85; N, 11.89. 

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

All H atoms were positioned geometrically \[C---H = 0.93, 0.96, 0.97 Å and N---H = 0.86 Å\] and allowed to ride on their parent atoms, with *U*~iso~(H) = 1.2--1.5*U*~eq~ of the C or N atom. 

Figures
=======

![ Molecular structure of the title compound with 50% probability displacement ellipsoids.](e-68-0o822-fig1){#Fap1}

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

  ------------------------- ---------------------------------------
  C~26~H~27~ClN~4~OS        *F*(000) = 1008
  *M~r~* = 479.03           *D*~x~ = 1.297 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Melting point: 462 K
  Hall symbol: -P 2ybc      Mo *K*α radiation, λ = 0.71073 Å
  *a* = 17.428 (13) Å       Cell parameters from 4592 reflections
  *b* = 9.391 (7) Å         θ = 2.5--27.5°
  *c* = 16.170 (13) Å       µ = 0.27 mm^−1^
  β = 111.995 (7)°          *T* = 296 K
  *V* = 2454 (3) Å^3^       Prism, colourless
  *Z* = 4                   0.26 × 0.24 × 0.20 mm
  ------------------------- ---------------------------------------

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

  --------------------------------------------------------------- --------------------------------------
  Bruker SMART CCD diffractometer                                 5611 independent reflections
  Radiation source: fine-focus sealed tube                        3883 reflections with *I* \> 2σ(*I*)
  Graphite monochromator                                          *R*~int~ = 0.090
  CCD Profile fitting scans                                       θ~max~ = 27.5°, θ~min~ = 2.5°
  Absorption correction: multi-scan (*SADABS*; Sheldrick, 1996)   *h* = −22→22
  *T*~min~ = 0.934, *T*~max~ = 0.949                              *k* = −12→12
  25485 measured reflections                                      *l* = −20→20
  --------------------------------------------------------------- --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.070   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.164                  H-atom parameters constrained
  *S* = 1.06                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0535*P*)^2^ + 1.2122*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  5611 reflections                      (Δ/σ)~max~ \< 0.001
  300 parameters                        Δρ~max~ = 0.36 e Å^−3^
  0 restraints                          Δρ~min~ = −0.26 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~   
  Cl1    0.63895 (6)    1.09995 (13)   0.09315 (7)     0.0814 (3)           
  C1     0.0316 (2)     1.1445 (5)     0.6378 (3)      0.0782 (11)          
  H1     −0.0188        1.1831         0.6337          0.094\*              
  C2     0.0970 (2)     1.2321 (4)     0.6461 (2)      0.0695 (10)          
  H2     0.0913         1.3303         0.6480          0.083\*              
  C3     0.1715 (2)     1.1734 (4)     0.6516 (2)      0.0585 (8)           
  H3     0.2158         1.2333         0.6577          0.070\*              
  C4     0.18193 (19)   1.0276 (3)     0.64841 (19)    0.0482 (7)           
  C5     0.1159 (2)     0.9416 (4)     0.6414 (3)      0.0692 (10)          
  H5     0.1215         0.8431         0.6404          0.083\*              
  C6     0.0411 (2)     1.0003 (5)     0.6358 (3)      0.0870 (13)          
  H6     −0.0032        0.9408         0.6305          0.104\*              
  C7     0.26265 (19)   0.9681 (4)     0.65007 (19)    0.0517 (7)           
  H7A    0.3077         1.0067         0.7009          0.062\*              
  H7B    0.2627         0.8654         0.6570          0.062\*              
  C8     0.35672 (18)   0.9495 (4)     0.57200 (19)    0.0515 (7)           
  H8A    0.3558         0.8462         0.5708          0.062\*              
  H8B    0.3992         0.9794         0.6278          0.062\*              
  C9     0.37759 (17)   1.0049 (4)     0.49451 (18)    0.0509 (7)           
  H9A    0.3894         1.1061         0.5020          0.061\*              
  H9B    0.4264         0.9567         0.4934          0.061\*              
  C10    0.30634 (16)   0.9793 (3)     0.40863 (17)    0.0399 (6)           
  C11    0.23083 (16)   0.9471 (3)     0.40872 (17)    0.0404 (6)           
  C12    0.20962 (17)   0.9400 (3)     0.49018 (18)    0.0470 (7)           
  H12A   0.1583         0.9908         0.4794          0.056\*              
  H12B   0.2016         0.8415         0.5030          0.056\*              
  C13    0.30607 (15)   0.9815 (3)     0.31940 (17)    0.0394 (6)           
  C14    0.23034 (16)   0.9494 (3)     0.25440 (18)    0.0407 (6)           
  C15    0.27191 (17)   0.9691 (3)     0.13904 (18)    0.0416 (6)           
  C16    0.37323 (17)   1.0126 (3)     0.29188 (18)    0.0429 (6)           
  C17    0.41915 (16)   1.0218 (3)     0.16662 (17)    0.0406 (6)           
  C18    0.43494 (19)   1.1580 (3)     0.1439 (2)      0.0519 (7)           
  H18    0.4005         1.2332         0.1445          0.062\*              
  C19    0.50245 (19)   1.1807 (4)     0.1202 (2)      0.0549 (8)           
  H19    0.5141         1.2717         0.1054          0.066\*              
  C20    0.55211 (18)   1.0682 (4)     0.11873 (19)    0.0511 (7)           
  C21    0.53581 (18)   0.9314 (4)     0.1390 (2)      0.0522 (8)           
  H21    0.5690         0.8558         0.1356          0.063\*              
  C22    0.46907 (18)   0.9086 (3)     0.16437 (19)    0.0474 (7)           
  H22    0.4580         0.8177         0.1798          0.057\*              
  C23    0.17702 (19)   0.9558 (3)     −0.01924 (19)   0.0538 (8)           
  H23A   0.1411         0.9049         0.0041          0.065\*              
  H23B   0.1808         0.9003         −0.0682         0.065\*              
  C24    0.1383 (2)     1.0970 (4)     −0.0548 (2)     0.0699 (10)          
  H24    0.1388         1.1552         −0.0043         0.084\*              
  C25    0.1863 (3)     1.1749 (5)     −0.1013 (3)     0.1069 (17)          
  H25A   0.2408         1.1960         −0.0591         0.160\*              
  H25B   0.1583         1.2620         −0.1261         0.160\*              
  H25C   0.1903         1.1162         −0.1481         0.160\*              
  C26    0.0481 (3)     1.0733 (6)     −0.1165 (3)     0.1126 (18)          
  H26A   0.0231         1.1631         −0.1401         0.169\*              
  H26B   0.0185         1.0301         −0.0835         0.169\*              
  H26C   0.0461         1.0118         −0.1647         0.169\*              
  N1     0.27599 (14)   1.0031 (3)     0.56719 (14)    0.0423 (5)           
  N2     0.21063 (14)   0.9434 (3)     0.16459 (15)    0.0438 (6)           
  N3     0.35216 (13)   0.9995 (3)     0.19807 (14)    0.0419 (5)           
  N4     0.25971 (15)   0.9662 (3)     0.05109 (15)    0.0527 (6)           
  H4     0.3020         0.9707         0.0360          0.079\*              
  S1     0.15757 (4)    0.91648 (9)    0.30144 (5)     0.0500 (2)           
  O1     0.44421 (12)   1.0478 (3)     0.33911 (13)    0.0578 (6)           
  ------ -------------- -------------- --------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- ------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^       *U*^23^
  Cl1   0.0590 (5)    0.1216 (9)    0.0769 (6)    −0.0133 (5)    0.0407 (5)    −0.0021 (6)
  C1    0.064 (2)     0.086 (3)     0.100 (3)     0.006 (2)      0.048 (2)     0.002 (2)
  C2    0.071 (2)     0.064 (2)     0.084 (3)     0.0060 (18)    0.042 (2)     −0.0009 (19)
  C3    0.0549 (19)   0.060 (2)     0.064 (2)     −0.0091 (15)   0.0263 (17)   −0.0018 (16)
  C4    0.0508 (17)   0.059 (2)     0.0379 (15)   −0.0035 (14)   0.0198 (14)   0.0015 (13)
  C5    0.070 (2)     0.062 (2)     0.084 (3)     −0.0081 (18)   0.039 (2)     0.0008 (18)
  C6    0.062 (2)     0.086 (3)     0.126 (4)     −0.018 (2)     0.051 (3)     −0.003 (3)
  C7    0.0520 (18)   0.062 (2)     0.0397 (16)   0.0025 (14)    0.0156 (14)   0.0039 (13)
  C8    0.0393 (16)   0.070 (2)     0.0397 (15)   0.0056 (14)    0.0086 (13)   0.0014 (14)
  C9    0.0308 (14)   0.079 (2)     0.0394 (15)   0.0008 (14)    0.0087 (12)   −0.0056 (14)
  C10   0.0313 (13)   0.0452 (16)   0.0382 (14)   0.0002 (11)    0.0074 (11)   −0.0034 (11)
  C11   0.0371 (14)   0.0460 (17)   0.0352 (13)   −0.0030 (11)   0.0102 (12)   −0.0041 (11)
  C12   0.0397 (15)   0.0570 (19)   0.0441 (16)   −0.0074 (13)   0.0154 (13)   −0.0044 (13)
  C13   0.0301 (13)   0.0477 (17)   0.0371 (14)   −0.0011 (11)   0.0087 (11)   −0.0014 (11)
  C14   0.0328 (14)   0.0461 (17)   0.0394 (14)   −0.0035 (11)   0.0091 (12)   −0.0007 (11)
  C15   0.0379 (14)   0.0441 (17)   0.0376 (14)   0.0008 (11)    0.0082 (12)   0.0002 (11)
  C16   0.0364 (14)   0.0502 (18)   0.0376 (14)   0.0011 (12)    0.0087 (12)   −0.0021 (12)
  C17   0.0358 (14)   0.0475 (17)   0.0365 (14)   −0.0018 (12)   0.0111 (12)   0.0013 (11)
  C18   0.0524 (18)   0.0488 (19)   0.0556 (18)   0.0061 (14)    0.0216 (15)   0.0053 (14)
  C19   0.0542 (18)   0.056 (2)     0.0566 (18)   −0.0067 (15)   0.0230 (16)   0.0079 (14)
  C20   0.0418 (16)   0.070 (2)     0.0422 (16)   −0.0064 (14)   0.0162 (14)   −0.0015 (14)
  C21   0.0429 (16)   0.063 (2)     0.0484 (17)   0.0054 (14)    0.0140 (14)   −0.0098 (14)
  C22   0.0459 (16)   0.0445 (17)   0.0498 (16)   −0.0005 (13)   0.0158 (14)   −0.0005 (13)
  C23   0.0480 (17)   0.066 (2)     0.0369 (15)   −0.0093 (14)   0.0037 (14)   0.0019 (13)
  C24   0.065 (2)     0.066 (2)     0.059 (2)     0.0075 (18)    0.0009 (18)   −0.0100 (17)
  C25   0.109 (4)     0.074 (3)     0.102 (3)     −0.022 (3)     −0.001 (3)    0.032 (3)
  C26   0.068 (3)     0.124 (4)     0.104 (4)     0.014 (3)      −0.015 (3)    0.004 (3)
  N1    0.0377 (12)   0.0533 (15)   0.0338 (11)   0.0022 (10)    0.0107 (10)   −0.0011 (10)
  N2    0.0344 (12)   0.0553 (16)   0.0363 (12)   −0.0041 (10)   0.0071 (10)   −0.0018 (10)
  N3    0.0338 (12)   0.0507 (15)   0.0380 (12)   −0.0038 (10)   0.0098 (10)   0.0003 (10)
  N4    0.0385 (13)   0.0814 (19)   0.0333 (12)   −0.0024 (12)   0.0079 (11)   0.0015 (11)
  S1    0.0332 (4)    0.0741 (6)    0.0398 (4)    −0.0117 (3)    0.0102 (3)    −0.0071 (3)
  O1    0.0337 (10)   0.0945 (18)   0.0403 (11)   −0.0104 (10)   0.0081 (9)    −0.0057 (10)
  ----- ------------- ------------- ------------- -------------- ------------- --------------

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

  ----------------------- ------------ ----------------------- ------------
  Cl1---C20               1.738 (3)    C14---N2                1.362 (4)
  C1---C6                 1.366 (6)    C14---S1                1.734 (3)
  C1---C2                 1.371 (5)    C15---N2                1.304 (3)
  C1---H1                 0.9300       C15---N4                1.357 (4)
  C2---C3                 1.382 (5)    C15---N3                1.396 (3)
  C2---H2                 0.9300       C16---O1                1.231 (3)
  C3---C4                 1.384 (5)    C16---N3                1.426 (4)
  C3---H3                 0.9300       C17---C22               1.383 (4)
  C4---C5                 1.375 (5)    C17---C18               1.386 (4)
  C4---C7                 1.505 (4)    C17---N3                1.453 (3)
  C5---C6                 1.388 (5)    C18---C19               1.383 (4)
  C5---H5                 0.9300       C18---H18               0.9300
  C6---H6                 0.9300       C19---C20               1.372 (4)
  C7---N1                 1.481 (4)    C19---H19               0.9300
  C7---H7A                0.9700       C20---C21               1.381 (4)
  C7---H7B                0.9700       C21---C22               1.387 (4)
  C8---N1                 1.469 (4)    C21---H21               0.9300
  C8---C9                 1.521 (4)    C22---H22               0.9300
  C8---H8A                0.9700       C23---N4                1.467 (4)
  C8---H8B                0.9700       C23---C24               1.501 (5)
  C9---C10                1.495 (4)    C23---H23A              0.9700
  C9---H9A                0.9700       C23---H23B              0.9700
  C9---H9B                0.9700       C24---C25               1.507 (6)
  C10---C11               1.351 (4)    C24---C26               1.530 (5)
  C10---C13               1.441 (4)    C24---H24               0.9800
  C11---C12               1.497 (4)    C25---H25A              0.9600
  C11---S1                1.750 (3)    C25---H25B              0.9600
  C12---N1                1.470 (3)    C25---H25C              0.9600
  C12---H12A              0.9700       C26---H26A              0.9600
  C12---H12B              0.9700       C26---H26B              0.9600
  C13---C14               1.378 (4)    C26---H26C              0.9600
  C13---C16               1.429 (4)    N4---H4                 0.8600
                                                               
  C6---C1---C2            119.6 (4)    O1---C16---N3           118.8 (3)
  C6---C1---H1            120.2        O1---C16---C13          127.7 (3)
  C2---C1---H1            120.2        N3---C16---C13          113.5 (2)
  C1---C2---C3            119.6 (4)    C22---C17---C18         120.8 (3)
  C1---C2---H2            120.2        C22---C17---N3          119.6 (3)
  C3---C2---H2            120.2        C18---C17---N3          119.4 (3)
  C2---C3---C4            121.7 (3)    C19---C18---C17         119.3 (3)
  C2---C3---H3            119.2        C19---C18---H18         120.3
  C4---C3---H3            119.2        C17---C18---H18         120.3
  C5---C4---C3            117.8 (3)    C20---C19---C18         119.6 (3)
  C5---C4---C7            122.1 (3)    C20---C19---H19         120.2
  C3---C4---C7            120.1 (3)    C18---C19---H19         120.2
  C4---C5---C6            120.6 (4)    C19---C20---C21         121.7 (3)
  C4---C5---H5            119.7        C19---C20---Cl1         118.9 (3)
  C6---C5---H5            119.7        C21---C20---Cl1         119.4 (2)
  C1---C6---C5            120.7 (4)    C20---C21---C22         118.9 (3)
  C1---C6---H6            119.6        C20---C21---H21         120.6
  C5---C6---H6            119.6        C22---C21---H21         120.6
  N1---C7---C4            111.3 (2)    C17---C22---C21         119.7 (3)
  N1---C7---H7A           109.4        C17---C22---H22         120.2
  C4---C7---H7A           109.4        C21---C22---H22         120.2
  N1---C7---H7B           109.4        N4---C23---C24          114.1 (3)
  C4---C7---H7B           109.4        N4---C23---H23A         108.7
  H7A---C7---H7B          108.0        C24---C23---H23A        108.7
  N1---C8---C9            111.0 (2)    N4---C23---H23B         108.7
  N1---C8---H8A           109.4        C24---C23---H23B        108.7
  C9---C8---H8A           109.4        H23A---C23---H23B       107.6
  N1---C8---H8B           109.4        C23---C24---C25         111.4 (3)
  C9---C8---H8B           109.4        C23---C24---C26         109.0 (3)
  H8A---C8---H8B          108.0        C25---C24---C26         111.8 (4)
  C10---C9---C8           109.8 (2)    C23---C24---H24         108.2
  C10---C9---H9A          109.7        C25---C24---H24         108.2
  C8---C9---H9A           109.7        C26---C24---H24         108.2
  C10---C9---H9B          109.7        C24---C25---H25A        109.5
  C8---C9---H9B           109.7        C24---C25---H25B        109.5
  H9A---C9---H9B          108.2        H25A---C25---H25B       109.5
  C11---C10---C13         111.5 (2)    C24---C25---H25C        109.5
  C11---C10---C9          120.4 (2)    H25A---C25---H25C       109.5
  C13---C10---C9          128.1 (2)    H25B---C25---H25C       109.5
  C10---C11---C12         124.9 (2)    C24---C26---H26A        109.5
  C10---C11---S1          112.7 (2)    C24---C26---H26B        109.5
  C12---C11---S1          122.4 (2)    H26A---C26---H26B       109.5
  N1---C12---C11          110.6 (2)    C24---C26---H26C        109.5
  N1---C12---H12A         109.5        H26A---C26---H26C       109.5
  C11---C12---H12A        109.5        H26B---C26---H26C       109.5
  N1---C12---H12B         109.5        C12---N1---C8           109.9 (2)
  C11---C12---H12B        109.5        C12---N1---C7           109.7 (2)
  H12A---C12---H12B       108.1        C8---N1---C7            110.4 (2)
  C14---C13---C16         118.0 (2)    C15---N2---C14          114.9 (2)
  C14---C13---C10         113.8 (2)    C15---N3---C16          122.5 (2)
  C16---C13---C10         128.2 (2)    C15---N3---C17          121.4 (2)
  N2---C14---C13          127.5 (3)    C16---N3---C17          116.1 (2)
  N2---C14---S1           121.8 (2)    C15---N4---C23          122.5 (3)
  C13---C14---S1          110.7 (2)    C15---N4---H4           118.8
  N2---C15---N4           120.2 (2)    C23---N4---H4           118.8
  N2---C15---N3           123.4 (2)    C14---S1---C11          91.35 (14)
  N4---C15---N3           116.4 (2)                            
                                                               
  C6---C1---C2---C3       0.4 (6)      C19---C20---C21---C22   −2.2 (5)
  C1---C2---C3---C4       0.5 (5)      Cl1---C20---C21---C22   176.3 (2)
  C2---C3---C4---C5       −1.4 (5)     C18---C17---C22---C21   0.0 (4)
  C2---C3---C4---C7       177.0 (3)    N3---C17---C22---C21    −176.5 (3)
  C3---C4---C5---C6       1.4 (5)      C20---C21---C22---C17   1.7 (4)
  C7---C4---C5---C6       −176.9 (4)   N4---C23---C24---C25    64.8 (4)
  C2---C1---C6---C5       −0.4 (7)     N4---C23---C24---C26    −171.4 (3)
  C4---C5---C6---C1       −0.5 (7)     C11---C12---N1---C8     −46.5 (3)
  C5---C4---C7---N1       110.2 (3)    C11---C12---N1---C7     −168.0 (2)
  C3---C4---C7---N1       −68.1 (4)    C9---C8---N1---C12      68.1 (3)
  N1---C8---C9---C10      −50.3 (3)    C9---C8---N1---C7       −170.8 (3)
  C8---C9---C10---C11     15.6 (4)     C4---C7---N1---C12      −61.3 (3)
  C8---C9---C10---C13     −163.2 (3)   C4---C7---N1---C8       177.5 (3)
  C13---C10---C11---C12   −178.3 (3)   N4---C15---N2---C14     −180.0 (3)
  C9---C10---C11---C12    2.7 (4)      N3---C15---N2---C14     0.5 (4)
  C13---C10---C11---S1    0.7 (3)      C13---C14---N2---C15    1.3 (4)
  C9---C10---C11---S1     −178.3 (2)   S1---C14---N2---C15     −179.3 (2)
  C10---C11---C12---N1    12.6 (4)     N2---C15---N3---C16     −3.5 (4)
  S1---C11---C12---N1     −166.3 (2)   N4---C15---N3---C16     177.0 (3)
  C11---C10---C13---C14   −0.7 (4)     N2---C15---N3---C17     177.5 (3)
  C9---C10---C13---C14    178.2 (3)    N4---C15---N3---C17     −2.0 (4)
  C11---C10---C13---C16   179.2 (3)    O1---C16---N3---C15     −175.8 (3)
  C9---C10---C13---C16    −1.9 (5)     C13---C16---N3---C15    4.3 (4)
  C16---C13---C14---N2    −0.1 (5)     O1---C16---N3---C17     3.3 (4)
  C10---C13---C14---N2    179.8 (3)    C13---C16---N3---C17    −176.6 (2)
  C16---C13---C14---S1    −179.6 (2)   C22---C17---N3---C15    −93.6 (3)
  C10---C13---C14---S1    0.3 (3)      C18---C17---N3---C15    89.9 (3)
  C14---C13---C16---O1    177.5 (3)    C22---C17---N3---C16    87.3 (3)
  C10---C13---C16---O1    −2.3 (5)     C18---C17---N3---C16    −89.2 (3)
  C14---C13---C16---N3    −2.6 (4)     N2---C15---N4---C23     9.3 (4)
  C10---C13---C16---N3    177.6 (3)    N3---C15---N4---C23     −171.2 (3)
  C22---C17---C18---C19   −1.2 (4)     C24---C23---N4---C15    92.6 (4)
  N3---C17---C18---C19    175.3 (3)    N2---C14---S1---C11     −179.4 (2)
  C17---C18---C19---C20   0.7 (5)      C13---C14---S1---C11    0.1 (2)
  C18---C19---C20---C21   1.0 (5)      C10---C11---S1---C14    −0.5 (2)
  C18---C19---C20---Cl1   −177.5 (2)   C12---C11---S1---C14    178.5 (3)
  ----------------------- ------------ ----------------------- ------------

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

  --------------------- --------- --------- ----------- ---------------
  *D*---H···*A*         *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  N4---H4···Cl1^i^      0.86      2.73      3.469 (3)   144
  C8---H8*B*···O1^ii^   0.97      2.59      3.220 (4)   123
  --------------------- --------- --------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*         *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  ------------------- --------- ------- ----------- -------------
  N4---H4⋯Cl1^i^      0.86      2.73    3.469 (3)   144
  C8---H8*B*⋯O1^ii^   0.97      2.59    3.220 (4)   123

Symmetry codes: (i) ; (ii) .