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

For background to thio­acetanilides, see: Peruncheralathan *et al.* ( 2005[@bb5]); Li *et al.* ( 2010[@bb2]); Wu *et al.* ( 2009[@bb10]); Erten-Ela *et al.* ( 2008[@bb1]); Tokoro *et al.* ( 2010[@bb8]); Lu *et al.* ( 2002[@bb3]); Tsuboyama *et al.* ( 2003[@bb9]); Zhang *et al.* ( 2006[@bb11]).  For the crystal structures of related compounds, see: Macedo *et al.* ( 2008[@bb4]). 

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~25~H~18~BClF~2~N~2~OS*M* *~r~* = 478.73Monoclinic,*a* = 9.6996 (19) Å*b* = 16.290 (3) Å*c* = 14.168 (3) Åβ = 98.71 (3)°*V* = 2212.9 (8) Å^3^*Z* = 4Mo *K*α radiationμ = 0.31 mm^−1^*T* = 173 K0.43 × 0.29 × 0.09 mm

### Data collection   {#sec2.1.2}

Rigaku MM007HF diffractometer with Saturn724+ CCDAbsorption correction: multi-scan (*CrystalClear-SM Expert*; Rigaku/MSC, 2008[@bb6]) *T* ~min~ = 0.685, *T* ~max~ = 1.00015558 measured reflections5081 independent reflections4491 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.052

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.058*wR*(*F* ^2^) = 0.120*S* = 1.185081 reflections298 parametersH-atom parameters constrainedΔρ~max~ = 0.31 e Å^−3^Δρ~min~ = −0.23 e Å^−3^

 {#d5e475}

Data collection: *CrystalClear-SM Expert* (Rigaku/MSC, 2008[@bb6]); cell refinement: *CrystalClear-SM Expert*; data reduction: *CrystalClear-SM Expert*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb7]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb7]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb7]); software used to prepare material for publication: *SHELXTL*. 

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

###### 

Click here for additional data file. 

Crystal structure: contains datablock(s) I, global.  DOI: [10.1107/S1600536813007800/cv5394sup1.cif](http://dx.doi.org/10.1107/S1600536813007800/cv5394sup1.cif)

###### 

Click here for additional data file. 

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536813007800/cv5394Isup2.hkl](http://dx.doi.org/10.1107/S1600536813007800/cv5394Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?cv5394&file=cv5394sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?cv5394sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?cv5394&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [CV5394](http://scripts.iucr.org/cgi-bin/sendsup?cv5394)). 

Comment
=======

Thioacetanilides being novel enaminones (Peruncheralathan *et al.*,  2005) with four active reaction sites show structural feature of highly polarized push-pull interaction C=C double bond (Li *et al.*,  2010).  BF~2~ complexes, such as the Bodipy family, are most intriguing due to their outstanding optical properties, extraordinary chemical versatility, and variety of applications spanning from biolabeling (Wu *et al.*,  2009) to solar cells (Erten-Ela *et al.*,  2008) and nanoparticle engineering (Tokoro *et al.*,  2010).  Synthetic studies have been conducted on various phosphorescent materials with heavy metals such as iridium (Tsuboyama *et al.*,  2003) and platinum (Lu *et al.*,  2002) and on fluorescent boron complexes (Zhang *et al.*,  2006).  In order to explore the chemical reactivities of thioacetanilides, we obtained the title compound, (I). 

In (I) (Fig.  1), the B1--N2 bond length (1.571 (3) Å) is more than 0.1 Å longer than the B1--O1 bond length (1.458 (3) Å) suggesting that the major resonance contribution to bonding is the alkoxy-imine form.  All bond lengths and angles in (I) are normal and in a good agreement with those reported previously for related compounds (Macedo *et al.*,  2008) The phenyl rings C10---C15 and C20---C25 form the dihedral angles of 83.1 (1) and 64.6 (1)°, respectively, with the chlorophenyl ring C1---C6. 

In the crystal, π-π interactions (centroid-to-centroid distances 3.877 (6) Å between the chlorophenyl rings of neighbouring molecules) and weak intermolecular C---H···N, C---H···F and C---H···π interactions (Table 1) held molecules together. 

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

A 25 ml volumetric flask was charged with 8 ml THF and 1.01 g (5 mmol) 2-cyano-1-phenylallyl acetate.  Then 1.45 g (5 mmol) 3-(4-chlorophenyl)-3-oxo-*N*-phenylpropane thioamide and 0.09 g (3.75 mmol) sodium hydride were added.  The mixture was stirred at room temperature for 4 h, and then 8 ml BF~3~.Et~2~O (10 mmol) was added with stirring for a further 4 h at room temperature.  The reaction was monitored by TLC, and after TLC indicated the completion of the reaction, the solution was filtered, and the inorganic salts were removed.  The solvent of the filtrate was removed with the aid of a rotary evaporator, and the residue was purified by column chromatography on silica gel, using petroleum ether/ethyl acetate (6:1) as eluent to provide the desired product yielding 2.01 g (84%) of pure BF2 complex, m.p.  462--463 K. Analytical data: IR (KBr, cm^-1^): 3080, 2977, 2180, 1681, 1583, 1505, 850, 732, 699.  ^1^H-NMR (500 MHz, CDCl~3~): δ (p.p.m.)  3.98 (2*H*, s), 6.26 (1*H*, s), 7.22 (1*H*, s), 7.32--7.33 (2*H*, d, J = 7.55 Hz), 7.40--7.49 (8*H*, m), 7.73--7.74 (2*H*, d, J = 7.65 Hz), 7.88--7.90 (2*H*, d, J = 4.28 Hz).  Single crystals suitable for X-ray diffraction were obtained through slow evaporation of a solution of the pure title compound in ethanol. 

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

All H atoms were found on difference maps, but placed in idealized positions (C--H = 0.95--0.99 Å), and included in the final cycles of refinement using a riding model, with *U*~iso~(H) = 1.2*U*~eq~(C). 

Figures
=======

![ View of (I) showing the atomic numbering and 40% probability displacement ellipsoids.](e-69-0o648-fig1){#Fap1}

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

  ------------------------- ---------------------------------------
  C~25~H~18~BClF~2~N~2~OS   *F*(000) = 984
  *M~r~* = 478.73           *D*~x~ = 1.437 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ybc      Cell parameters from 7694 reflections
  *a* = 9.6996 (19) Å       θ = 1.5--27.5°
  *b* = 16.290 (3) Å        µ = 0.31 mm^−1^
  *c* = 14.168 (3) Å        *T* = 173 K
  β = 98.71 (3)°            Plate, colourless
  *V* = 2212.9 (8) Å^3^     0.43 × 0.29 × 0.09 mm
  *Z* = 4                   
  ------------------------- ---------------------------------------

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

  -------------------------------------------------------------------------------- --------------------------------------
  Rigaku MM007HF diffractometer with Saturn724+ CCD                                5081 independent reflections
  Radiation source: Rotating Anode                                                 4491 reflections with *I* \> 2σ(*I*)
  Confocal monochromator                                                           *R*~int~ = 0.052
  Detector resolution: 28.5714 pixels mm^-1^                                       θ~max~ = 27.5°, θ~min~ = 2.1°
  ω scans at fixed χ = 45°                                                         *h* = −12→12
  Absorption correction: multi-scan (*CrystalClear-SM Expert*; Rigaku/MSC, 2008)   *k* = −20→21
  *T*~min~ = 0.685, *T*~max~ = 1.000                                               *l* = −18→18
  15558 measured reflections                                                       
  -------------------------------------------------------------------------------- --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.058   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.120                  H-atom parameters constrained
  *S* = 1.18                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0312*P*)^2^ + 1.2135*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  5081 reflections                      (Δ/σ)~max~ = 0.001
  298 parameters                        Δρ~max~ = 0.31 e Å^−3^
  0 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~   
  Cl1    1.18430 (6)    0.47712 (4)    1.29061 (4)    0.03843 (16)         
  S1     0.47463 (6)    0.63647 (4)    0.79190 (4)    0.03476 (16)         
  F1     0.61480 (16)   0.34159 (9)    0.78320 (10)   0.0494 (4)           
  F2     0.46844 (15)   0.35602 (9)    0.89236 (12)   0.0531 (4)           
  O1     0.69166 (16)   0.40858 (9)    0.92380 (11)   0.0328 (4)           
  N1     0.7666 (3)     0.74393 (18)   0.69117 (18)   0.0609 (7)           
  N2     0.51593 (17)   0.47557 (11)   0.80301 (12)   0.0262 (4)           
  C1     1.0468 (2)     0.47953 (14)   1.19668 (15)   0.0274 (5)           
  C2     1.0082 (2)     0.55340 (14)   1.15244 (16)   0.0304 (5)           
  H2     1.0558         0.6027         1.1730         0.036\*              
  C3     0.8982 (2)     0.55382 (13)   1.07731 (16)   0.0292 (5)           
  H3     0.8696         0.6041         1.0465         0.035\*              
  C4     0.8293 (2)     0.48155 (13)   1.04648 (15)   0.0250 (4)           
  C5     0.8714 (2)     0.40787 (13)   1.09205 (16)   0.0292 (5)           
  H5     0.8256         0.3582         1.0709         0.035\*              
  C6     0.9795 (2)     0.40674 (14)   1.16804 (16)   0.0299 (5)           
  H6     1.0071         0.3568         1.2000         0.036\*              
  C7     0.7153 (2)     0.48088 (13)   0.96488 (15)   0.0248 (4)           
  C8     0.6431 (2)     0.54917 (13)   0.93219 (15)   0.0275 (5)           
  H8     0.6567         0.5989         0.9674         0.033\*              
  C9     0.5476 (2)     0.54684 (13)   0.84604 (15)   0.0261 (4)           
  C10    0.4192 (2)     0.47173 (13)   0.71416 (15)   0.0264 (4)           
  C11    0.4659 (2)     0.44916 (14)   0.63062 (15)   0.0299 (5)           
  H11    0.5618         0.4376         0.6303         0.036\*              
  C12    0.3708 (2)     0.44347 (14)   0.54681 (16)   0.0332 (5)           
  H12    0.4020         0.4278         0.4890         0.040\*              
  C13    0.2318 (2)     0.46038 (15)   0.54715 (17)   0.0353 (5)           
  H13    0.1674         0.4568         0.4897         0.042\*              
  C14    0.1866 (2)     0.48238 (16)   0.63088 (17)   0.0371 (6)           
  H14    0.0907         0.4944         0.6309         0.044\*              
  C15    0.2795 (2)     0.48729 (15)   0.71564 (17)   0.0351 (5)           
  H15    0.2475         0.5012         0.7737         0.042\*              
  C16    0.5544 (2)     0.71958 (13)   0.86749 (16)   0.0305 (5)           
  H16A   0.4994         0.7701         0.8507         0.037\*              
  H16B   0.5464         0.7061         0.9346         0.037\*              
  C17    0.7407 (2)     0.74202 (16)   0.76730 (19)   0.0392 (6)           
  C18    0.7058 (2)     0.73849 (13)   0.86224 (16)   0.0290 (5)           
  C19    0.7974 (2)     0.75408 (13)   0.94089 (17)   0.0298 (5)           
  H19    0.7598         0.7497         0.9988         0.036\*              
  C20    0.9453 (2)     0.77676 (13)   0.95341 (18)   0.0331 (5)           
  C21    1.0184 (3)     0.77306 (15)   1.04606 (19)   0.0399 (6)           
  H21    0.9705         0.7581         1.0972         0.048\*              
  C22    1.1595 (3)     0.79076 (17)   1.0647 (2)     0.0497 (7)           
  H22    1.2079         0.7870         1.1281         0.060\*              
  C23    1.2294 (3)     0.81371 (17)   0.9917 (3)     0.0549 (8)           
  H23    1.3263         0.8257         1.0045         0.066\*              
  C24    1.1594 (3)     0.81935 (16)   0.8998 (2)     0.0525 (8)           
  H24    1.2083         0.8351         0.8494         0.063\*              
  C25    1.0182 (3)     0.80214 (15)   0.8805 (2)     0.0412 (6)           
  H25    0.9703         0.8076         0.8172         0.049\*              
  B1     0.5719 (3)     0.39255 (16)   0.85061 (19)   0.0319 (6)           
  ------ -------------- -------------- -------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  Cl1   0.0282 (3)    0.0561 (4)    0.0277 (3)    0.0032 (2)     −0.0063 (2)    −0.0049 (3)
  S1    0.0339 (3)    0.0328 (3)    0.0334 (3)    0.0042 (2)     −0.0084 (2)    0.0026 (2)
  F1    0.0668 (10)   0.0414 (8)    0.0339 (8)    0.0178 (7)     −0.0125 (7)    −0.0125 (6)
  F2    0.0451 (9)    0.0497 (9)    0.0622 (11)   −0.0141 (7)    0.0003 (7)     0.0157 (8)
  O1    0.0389 (9)    0.0252 (8)    0.0294 (9)    0.0015 (7)     −0.0102 (7)    −0.0042 (6)
  N1    0.0547 (15)   0.090 (2)     0.0404 (15)   0.0242 (14)    0.0130 (11)    0.0166 (13)
  N2    0.0249 (9)    0.0321 (10)   0.0201 (9)    −0.0005 (7)    −0.0013 (7)    −0.0020 (7)
  C1    0.0232 (10)   0.0402 (12)   0.0181 (11)   0.0031 (9)     0.0005 (8)     −0.0029 (9)
  C2    0.0307 (11)   0.0330 (12)   0.0266 (12)   −0.0051 (9)    0.0020 (9)     −0.0050 (9)
  C3    0.0328 (11)   0.0278 (11)   0.0256 (12)   −0.0010 (9)    −0.0003 (9)    −0.0007 (9)
  C4    0.0265 (10)   0.0281 (11)   0.0197 (11)   0.0020 (8)     0.0014 (8)     −0.0020 (8)
  C5    0.0317 (11)   0.0278 (11)   0.0266 (12)   0.0011 (9)     −0.0004 (8)    −0.0011 (9)
  C6    0.0325 (11)   0.0287 (11)   0.0265 (12)   0.0060 (9)     −0.0014 (9)    −0.0004 (9)
  C7    0.0277 (10)   0.0263 (11)   0.0202 (11)   −0.0026 (8)    0.0029 (8)     −0.0011 (8)
  C8    0.0294 (11)   0.0279 (11)   0.0229 (11)   0.0006 (9)     −0.0029 (8)    −0.0035 (8)
  C9    0.0246 (10)   0.0308 (11)   0.0222 (11)   −0.0003 (8)    0.0011 (8)     −0.0006 (8)
  C10   0.0266 (10)   0.0297 (11)   0.0214 (11)   −0.0042 (9)    −0.0011 (8)    0.0017 (8)
  C11   0.0271 (11)   0.0366 (12)   0.0251 (12)   −0.0038 (9)    0.0014 (8)     −0.0026 (9)
  C12   0.0390 (12)   0.0392 (13)   0.0210 (12)   −0.0095 (10)   0.0036 (9)     −0.0018 (9)
  C13   0.0352 (12)   0.0430 (14)   0.0245 (12)   −0.0097 (10)   −0.0061 (9)    0.0050 (10)
  C14   0.0254 (11)   0.0512 (15)   0.0326 (13)   −0.0026 (10)   −0.0020 (9)    0.0011 (11)
  C15   0.0278 (11)   0.0507 (15)   0.0267 (13)   −0.0038 (10)   0.0035 (9)     −0.0049 (10)
  C16   0.0297 (11)   0.0288 (11)   0.0317 (13)   0.0074 (9)     0.0002 (9)     0.0004 (9)
  C17   0.0345 (12)   0.0473 (15)   0.0353 (15)   0.0106 (11)    0.0041 (10)    0.0065 (11)
  C18   0.0318 (11)   0.0246 (10)   0.0311 (12)   0.0071 (9)     0.0066 (9)     0.0030 (9)
  C19   0.0331 (11)   0.0248 (11)   0.0317 (13)   0.0024 (9)     0.0058 (9)     0.0010 (9)
  C20   0.0330 (11)   0.0214 (10)   0.0449 (15)   0.0013 (9)     0.0061 (10)    0.0002 (10)
  C21   0.0380 (13)   0.0353 (13)   0.0452 (16)   −0.0021 (10)   0.0029 (11)    −0.0054 (11)
  C22   0.0386 (14)   0.0444 (15)   0.0616 (19)   −0.0029 (12)   −0.0067 (12)   −0.0058 (13)
  C23   0.0334 (13)   0.0383 (15)   0.092 (3)     −0.0078 (12)   0.0072 (14)    −0.0011 (15)
  C24   0.0411 (14)   0.0341 (14)   0.086 (2)     −0.0042 (12)   0.0215 (15)    0.0109 (14)
  C25   0.0397 (13)   0.0314 (13)   0.0536 (17)   0.0016 (10)    0.0105 (11)    0.0096 (11)
  B1    0.0342 (13)   0.0305 (13)   0.0284 (14)   −0.0032 (11)   −0.0040 (10)   −0.0041 (10)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

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

  ----------------------- -------------- ----------------------- --------------
  Cl1---C1                1.736 (2)      C11---C12               1.392 (3)
  S1---C9                 1.748 (2)      C11---H11               0.9500
  S1---C16                1.824 (2)      C12---C13               1.377 (3)
  F1---B1                 1.376 (3)      C12---H12               0.9500
  F2---B1                 1.375 (3)      C13---C14               1.373 (3)
  O1---C7                 1.318 (2)      C13---H13               0.9500
  O1---B1                 1.458 (3)      C14---C15               1.391 (3)
  N1---C17                1.144 (3)      C14---H14               0.9500
  N2---C9                 1.326 (3)      C15---H15               0.9500
  N2---C10                1.453 (3)      C16---C18               1.513 (3)
  N2---B1                 1.571 (3)      C16---H16A              0.9900
  C1---C2                 1.382 (3)      C16---H16B              0.9900
  C1---C6                 1.384 (3)      C17---C18               1.437 (3)
  C2---C3                 1.388 (3)      C18---C19               1.340 (3)
  C2---H2                 0.9500         C19---C20               1.466 (3)
  C3---C4                 1.391 (3)      C19---H19               0.9500
  C3---H3                 0.9500         C20---C21               1.396 (3)
  C4---C5                 1.394 (3)      C20---C25               1.400 (3)
  C4---C7                 1.474 (3)      C21---C22               1.384 (3)
  C5---C6                 1.385 (3)      C21---H21               0.9500
  C5---H5                 0.9500         C22---C23               1.372 (4)
  C6---H6                 0.9500         C22---H22               0.9500
  C7---C8                 1.358 (3)      C23---C24               1.377 (4)
  C8---C9                 1.417 (3)      C23---H23               0.9500
  C8---H8                 0.9500         C24---C25               1.384 (4)
  C10---C11               1.380 (3)      C24---H24               0.9500
  C10---C15               1.381 (3)      C25---H25               0.9500
                                                                 
  C9---S1---C16           104.75 (10)    C13---C14---C15         120.7 (2)
  C7---O1---B1            122.73 (17)    C13---C14---H14         119.6
  C9---N2---C10           120.69 (18)    C15---C14---H14         119.6
  C9---N2---B1            121.04 (17)    C10---C15---C14         119.0 (2)
  C10---N2---B1           118.08 (17)    C10---C15---H15         120.5
  C2---C1---C6            121.98 (19)    C14---C15---H15         120.5
  C2---C1---Cl1           119.43 (17)    C18---C16---S1          116.79 (16)
  C6---C1---Cl1           118.60 (17)    C18---C16---H16A        108.1
  C1---C2---C3            118.4 (2)      S1---C16---H16A         108.1
  C1---C2---H2            120.8          C18---C16---H16B        108.1
  C3---C2---H2            120.8          S1---C16---H16B         108.1
  C2---C3---C4            120.9 (2)      H16A---C16---H16B       107.3
  C2---C3---H3            119.6          N1---C17---C18          178.8 (3)
  C4---C3---H3            119.6          C19---C18---C17         123.4 (2)
  C3---C4---C5            119.35 (19)    C19---C18---C16         121.6 (2)
  C3---C4---C7            121.36 (19)    C17---C18---C16         115.0 (2)
  C5---C4---C7            119.27 (19)    C18---C19---C20         131.4 (2)
  C6---C5---C4            120.4 (2)      C18---C19---H19         114.3
  C6---C5---H5            119.8          C20---C19---H19         114.3
  C4---C5---H5            119.8          C21---C20---C25         117.7 (2)
  C1---C6---C5            119.0 (2)      C21---C20---C19         116.8 (2)
  C1---C6---H6            120.5          C25---C20---C19         125.4 (2)
  C5---C6---H6            120.5          C22---C21---C20         121.2 (3)
  O1---C7---C8            122.33 (19)    C22---C21---H21         119.4
  O1---C7---C4            114.39 (18)    C20---C21---H21         119.4
  C8---C7---C4            123.25 (19)    C23---C22---C21         120.0 (3)
  C7---C8---C9            120.5 (2)      C23---C22---H22         120.0
  C7---C8---H8            119.7          C21---C22---H22         120.0
  C9---C8---H8            119.7          C22---C23---C24         120.1 (3)
  N2---C9---C8            119.69 (19)    C22---C23---H23         119.9
  N2---C9---S1            118.65 (15)    C24---C23---H23         119.9
  C8---C9---S1            121.61 (16)    C23---C24---C25         120.3 (3)
  C11---C10---C15         120.8 (2)      C23---C24---H24         119.9
  C11---C10---N2          120.13 (19)    C25---C24---H24         119.9
  C15---C10---N2          119.0 (2)      C24---C25---C20         120.7 (3)
  C10---C11---C12         119.2 (2)      C24---C25---H25         119.7
  C10---C11---H11         120.4          C20---C25---H25         119.7
  C12---C11---H11         120.4          F2---B1---F1            110.8 (2)
  C13---C12---C11         120.4 (2)      F2---B1---O1            109.0 (2)
  C13---C12---H12         119.8          F1---B1---O1            108.0 (2)
  C11---C12---H12         119.8          F2---B1---N2            109.24 (19)
  C14---C13---C12         119.8 (2)      F1---B1---N2            110.0 (2)
  C14---C13---H13         120.1          O1---B1---N2            109.71 (18)
  C12---C13---H13         120.1                                  
                                                                 
  C6---C1---C2---C3       0.2 (3)        C10---C11---C12---C13   0.2 (3)
  Cl1---C1---C2---C3      179.82 (17)    C11---C12---C13---C14   −0.5 (4)
  C1---C2---C3---C4       −0.7 (3)       C12---C13---C14---C15   −0.4 (4)
  C2---C3---C4---C5       0.2 (3)        C11---C10---C15---C14   −2.0 (4)
  C2---C3---C4---C7       −178.1 (2)     N2---C10---C15---C14    −179.0 (2)
  C3---C4---C5---C6       0.8 (3)        C13---C14---C15---C10   1.6 (4)
  C7---C4---C5---C6       179.1 (2)      C9---S1---C16---C18     72.85 (18)
  C2---C1---C6---C5       0.8 (3)        N1---C17---C18---C19    157 (14)
  Cl1---C1---C6---C5      −178.86 (17)   N1---C17---C18---C16    −26 (14)
  C4---C5---C6---C1       −1.3 (3)       S1---C16---C18---C19    −137.62 (19)
  B1---O1---C7---C8       −10.5 (3)      S1---C16---C18---C17    45.1 (2)
  B1---O1---C7---C4       171.5 (2)      C17---C18---C19---C20   −0.2 (4)
  C3---C4---C7---O1       158.4 (2)      C16---C18---C19---C20   −177.3 (2)
  C5---C4---C7---O1       −19.9 (3)      C18---C19---C20---C21   −167.7 (2)
  C3---C4---C7---C8       −19.6 (3)      C18---C19---C20---C25   12.7 (4)
  C5---C4---C7---C8       162.2 (2)      C25---C20---C21---C22   −2.5 (4)
  O1---C7---C8---C9       −6.2 (3)       C19---C20---C21---C22   177.9 (2)
  C4---C7---C8---C9       171.6 (2)      C20---C21---C22---C23   1.1 (4)
  C10---N2---C9---C8      −179.45 (19)   C21---C22---C23---C24   0.1 (4)
  B1---N2---C9---C8       5.6 (3)        C22---C23---C24---C25   0.2 (4)
  C10---N2---C9---S1      −1.9 (3)       C23---C24---C25---C20   −1.7 (4)
  B1---N2---C9---S1       −176.82 (16)   C21---C20---C25---C24   2.8 (4)
  C7---C8---C9---N2       8.1 (3)        C19---C20---C25---C24   −177.7 (2)
  C7---C8---C9---S1       −169.38 (17)   C7---O1---B1---F2       −97.9 (2)
  C16---S1---C9---N2      −175.52 (17)   C7---O1---B1---F1       141.6 (2)
  C16---S1---C9---C8      2.0 (2)        C7---O1---B1---N2       21.6 (3)
  C9---N2---C10---C11     112.8 (2)      C9---N2---B1---F2       100.3 (2)
  B1---N2---C10---C11     −72.1 (3)      C10---N2---B1---F2      −74.8 (3)
  C9---N2---C10---C15     −70.1 (3)      C9---N2---B1---F1       −137.9 (2)
  B1---N2---C10---C15     105.0 (2)      C10---N2---B1---F1      47.0 (3)
  C15---C10---C11---C12   1.1 (3)        C9---N2---B1---O1       −19.2 (3)
  N2---C10---C11---C12    178.1 (2)      C10---N2---B1---O1      165.75 (18)
  ----------------------- -------------- ----------------------- --------------

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

Cg1 is the centroid of the C1--C6 ring. 

  ------------------------ --------- --------- ----------- ---------------
  *D*---H···*A*            *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C16---H16*A*···F1^i^     0.99      2.35      3.184 (3)   141
  C21---H21···N1^ii^       0.95      2.55      3.434 (4)   156
  C15---H15···*Cg*1^iii^   0.95      2.52      3.394 (5)   153
  ------------------------ --------- --------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

*Cg*1 is the centroid of the C1--C6 ring. 

  *D*---H⋯*A*            *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  ---------------------- --------- ------- ----------- -------------
  C16---H16*A*⋯F1^i^     0.99      2.35    3.184 (3)   141
  C21---H21⋯N1^ii^       0.95      2.55    3.434 (4)   156
  C15---H15⋯*Cg*1^iii^   0.95      2.52    3.394 (5)   153

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