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

For background to fluorine-containing heterocycles and their properties, see: Krishnaiah & Narsaiah (2002[@bb1]); Ohno *et al.* (2004[@bb2]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~14~H~10~F~6~N~6~*M* *~r~* = 376.28Monoclinic,*a* = 8.5387 (14) Å*b* = 16.110 (6) Å*c* = 11.022 (5) Åβ = 99.295 (5)°*V* = 1496.2 (9) Å^3^*Z* = 4Mo *K*α radiationμ = 0.16 mm^−1^*T* = 173 K0.41 × 0.36 × 0.26 mm

### Data collection {#sec2.1.2}

Rigaku Saturn724+ CCD diffractometerAbsorption correction: multi-scan (*CrystalClear*; Rigaku, 2008[@bb3]) *T* ~min~ = 0.938, *T* ~max~ = 0.9608915 measured reflections1706 independent reflections1678 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.033

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.047*wR*(*F* ^2^) = 0.100*S* = 1.191706 reflections120 parametersH-atom parameters constrainedΔρ~max~ = 0.23 e Å^−3^Δρ~min~ = −0.22 e Å^−3^

 {#d5e330}

Data collection: *CrystalClear* (Rigaku, 2008[@bb3]); cell refinement: *CrystalClear*; data reduction: *CrystalClear*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb4]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb4]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb4]); software used to prepare material for publication: *SHELXL97*.

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

Crystal structure: contains datablocks I, global. DOI: [10.1107/S1600536809043657/hb5156sup1.cif](http://dx.doi.org/10.1107/S1600536809043657/hb5156sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536809043657/hb5156Isup2.hkl](http://dx.doi.org/10.1107/S1600536809043657/hb5156Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?hb5156&file=hb5156sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?hb5156sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?hb5156&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [HB5156](http://scripts.iucr.org/cgi-bin/sendsup?hb5156)).

This work was supported by the China Postdoctoral Science Foundation (No. 20070420444), the Major State Basic Research Development program of China (No. 2010CB126106 and No. 2006CB101907), and the 863 high-tech key project of China (2006AA10A203).

Comment
=======

Strategically positioned fluorine in heterocyclic compounds, especially those containing trifluromethyl groups plays an important role in medicines and agrochemicals (e.g. Krishnaiah & Narsaiah, 2002). Specifically, the fluorinated pyrazoles have been shown to possess high biological activities (e.g. Ohno *et al.* 2004) as herbicides, fungicides, insecticides, analgesics, antipyretics and antiinflammatories. Pyrazolopyrimidine and related fuesd heterocycles are of interest as potential bioactive molecules. Recently, the new title compound (I) was synthesized in our group with high herbicidal activity. The crystal structure of the compound (I) is shown in Fig. 1.

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

The title compound (0.1 g) was dissolved in anhydrous methanol (20 ml) at room temperature. Colourless blocks of (I) were obtained through slow evaporation after two weeks.

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

All the hydrogen atoms were placed in idealised positions with C---H = 0.93--0.98Å and *U*~iso~(H) = 1.2--1.5*U*~ep~ (C).

Figures
=======

![The molecular structure of the title compound showing 50% probability displacement ellipsoids and atom-numbering scheme.](e-65-o2865-fig1){#Fap1}

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

  ----------------------- --------------------------------------
  C~14~H~10~F~6~N~6~      *F*(000) = 760
  *M~r~* = 376.28         *D*~x~ = 1.670 Mg m^−3^
  Monoclinic, *C*2/*c*    Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -C 2yc     Cell parameters from 648 reflections
  *a* = 8.5387 (14) Å     θ = 2.2--27.5°
  *b* = 16.110 (6) Å      µ = 0.16 mm^−1^
  *c* = 11.022 (5) Å      *T* = 173 K
  β = 99.295 (5)°         Block, colorless
  *V* = 1496.2 (9) Å^3^   0.41 × 0.36 × 0.26 mm
  *Z* = 4                 
  ----------------------- --------------------------------------

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

  ------------------------------------------------------------------ --------------------------------------
  Rigaku Saturn724+ CCD diffractometer                               1706 independent reflections
  Radiation source: sealed tube                                      1678 reflections with *I* \> 2σ(*I*)
  graphite                                                           *R*~int~ = 0.033
  ω scans at fixed χ = 45°                                           θ~max~ = 27.5°, θ~min~ = 2.7°
  Absorption correction: multi-scan (*CrystalClear*; Rigaku, 2008)   *h* = −11→11
  *T*~min~ = 0.938, *T*~max~ = 0.960                                 *k* = −20→20
  8915 measured reflections                                          *l* = −14→14
  ------------------------------------------------------------------ --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.047   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.100                  H-atom parameters constrained
  *S* = 1.19                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0291*P*)^2^ + 1.4916*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  1706 reflections                      (Δ/σ)~max~ \< 0.001
  120 parameters                        Δρ~max~ = 0.23 e Å^−3^
  0 restraints                          Δρ~min~ = −0.22 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~   
  F1    0.53252 (12)   0.61885 (7)    0.61601 (11)   0.0484 (3)           
  F2    0.39212 (17)   0.66320 (8)    0.45033 (11)   0.0610 (4)           
  F3    0.31154 (14)   0.67824 (7)    0.62363 (12)   0.0544 (3)           
  N1    0.22004 (15)   0.52452 (8)    0.43231 (12)   0.0284 (3)           
  N2    0.16127 (15)   0.44751 (8)    0.45125 (11)   0.0269 (3)           
  N3    0.07685 (16)   0.32384 (8)    0.35077 (13)   0.0311 (3)           
  C1    0.30268 (18)   0.54413 (10)   0.54059 (14)   0.0288 (3)           
  C2    0.29725 (19)   0.48203 (10)   0.62924 (14)   0.0310 (4)           
  H2A   0.3470         0.4829         0.7128         0.037\*              
  C3    0.20539 (18)   0.42006 (10)   0.57018 (14)   0.0289 (3)           
  C4    0.1508 (2)     0.34123 (11)   0.62036 (16)   0.0369 (4)           
  H4A   0.1750         0.3423         0.7103         0.055\*              
  H4B   0.2054         0.2942         0.5892         0.055\*              
  H4C   0.0360         0.3353         0.5945         0.055\*              
  C5    0.07580 (17)   0.40647 (10)   0.34787 (13)   0.0266 (3)           
  C6    0.0000         0.45258 (14)   0.2500         0.0265 (4)           
  H6A   0.0000         0.5115         0.2500         0.032\*              
  C7    0.0000         0.28736 (15)   0.2500         0.0331 (5)           
  H7A   0.0000         0.2284         0.2500         0.040\*              
  C8    0.3840 (2)     0.62608 (11)   0.55639 (15)   0.0342 (4)           
  ----- -------------- -------------- -------------- -------------------- --

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

  ---- ------------- ------------- ------------- ------------- ------------- -------------
       *U*^11^       *U*^22^       *U*^33^       *U*^12^       *U*^13^       *U*^23^
  F1   0.0298 (5)    0.0524 (7)    0.0594 (7)    −0.0036 (5)   −0.0038 (5)   −0.0096 (5)
  F2   0.0863 (10)   0.0544 (7)    0.0384 (6)    −0.0291 (7)   −0.0011 (6)   0.0066 (5)
  F3   0.0461 (7)    0.0431 (6)    0.0754 (9)    0.0017 (5)    0.0146 (6)    −0.0206 (6)
  N1   0.0275 (6)    0.0310 (7)    0.0259 (6)    −0.0002 (5)   0.0011 (5)    −0.0002 (5)
  N2   0.0254 (6)    0.0302 (7)    0.0242 (6)    0.0013 (5)    0.0014 (5)    0.0006 (5)
  N3   0.0300 (7)    0.0313 (7)    0.0311 (7)    0.0019 (5)    0.0023 (5)    0.0010 (6)
  C1   0.0251 (7)    0.0353 (8)    0.0256 (7)    0.0034 (6)    0.0027 (6)    −0.0028 (6)
  C2   0.0288 (8)    0.0393 (9)    0.0239 (7)    0.0063 (6)    0.0013 (6)    −0.0011 (6)
  C3   0.0270 (7)    0.0350 (8)    0.0244 (7)    0.0070 (6)    0.0038 (6)    0.0024 (6)
  C4   0.0432 (10)   0.0373 (9)    0.0296 (8)    0.0035 (7)    0.0044 (7)    0.0062 (7)
  C5   0.0223 (7)    0.0324 (8)    0.0252 (7)    0.0012 (6)    0.0043 (6)    −0.0016 (6)
  C6   0.0236 (10)   0.0292 (11)   0.0262 (10)   0.000         0.0028 (8)    0.000
  C7   0.0341 (12)   0.0291 (11)   0.0352 (12)   0.000         0.0032 (9)    0.000
  C8   0.0318 (8)    0.0394 (9)    0.0304 (8)    0.0008 (7)    0.0014 (6)    −0.0031 (7)
  ---- ------------- ------------- ------------- ------------- ------------- -------------

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

  ------------------- -------------- ---------------------- --------------
  F1---C8             1.3359 (19)    C2---C3                1.368 (2)
  F2---C8             1.325 (2)      C2---H2A               0.9500
  F3---C8             1.336 (2)      C3---C4                1.490 (2)
  N1---C1             1.323 (2)      C4---H4A               0.9800
  N1---N2             1.3668 (19)    C4---H4B               0.9800
  N2---C3             1.377 (2)      C4---H4C               0.9800
  N2---C5             1.414 (2)      C5---C6                1.3815 (19)
  N3---C5             1.331 (2)      C6---C5^i^             1.3815 (19)
  N3---C7             1.3319 (17)    C6---H6A               0.9500
  C1---C2             1.404 (2)      C7---N3^i^             1.3319 (17)
  C1---C8             1.489 (2)      C7---H7A               0.9500
                                                            
  C1---N1---N2        103.56 (13)    H4A---C4---H4C         109.5
  N1---N2---C3        112.71 (12)    H4B---C4---H4C         109.5
  N1---N2---C5        117.12 (12)    N3---C5---C6           123.83 (15)
  C3---N2---C5        130.02 (14)    N3---C5---N2           116.59 (13)
  C5---N3---C7        114.87 (15)    C6---C5---N2           119.57 (15)
  N1---C1---C2        112.63 (15)    C5^i^---C6---C5        114.9 (2)
  N1---C1---C8        119.21 (14)    C5^i^---C6---H6A       122.5
  C2---C1---C8        128.13 (15)    C5---C6---H6A          122.5
  C3---C2---C1        105.64 (14)    N3---C7---N3^i^        127.6 (2)
  C3---C2---H2A       127.2          N3---C7---H7A          116.2
  C1---C2---H2A       127.2          N3^i^---C7---H7A       116.2
  C2---C3---N2        105.44 (14)    F2---C8---F1           107.01 (15)
  C2---C3---C4        129.45 (15)    F2---C8---F3           107.49 (16)
  N2---C3---C4        124.98 (15)    F1---C8---F3           105.65 (14)
  C3---C4---H4A       109.5          F2---C8---C1           112.77 (14)
  C3---C4---H4B       109.5          F1---C8---C1           111.59 (14)
  H4A---C4---H4B      109.5          F3---C8---C1           111.93 (14)
  C3---C4---H4C       109.5                                 
                                                            
  C1---N1---N2---C3   0.68 (16)      N1---N2---C5---N3      152.46 (14)
  C1---N1---N2---C5   −175.36 (13)   C3---N2---C5---N3      −22.8 (2)
  N2---N1---C1---C2   −0.63 (17)     N1---N2---C5---C6      −26.16 (18)
  N2---N1---C1---C8   −179.10 (13)   C3---N2---C5---C6      158.62 (13)
  N1---C1---C2---C3   0.37 (18)      N3---C5---C6---C5^i^   −0.48 (11)
  C8---C1---C2---C3   178.67 (15)    N2---C5---C6---C5^i^   178.03 (15)
  C1---C2---C3---N2   0.07 (17)      C5---N3---C7---N3^i^   −0.43 (10)
  C1---C2---C3---C4   −175.86 (16)   N1---C1---C8---F2      −14.0 (2)
  N1---N2---C3---C2   −0.47 (17)     C2---C1---C8---F2      167.76 (16)
  C5---N2---C3---C2   174.92 (14)    N1---C1---C8---F1      −134.52 (15)
  N1---N2---C3---C4   175.69 (14)    C2---C1---C8---F1      47.3 (2)
  C5---N2---C3---C4   −8.9 (3)       N1---C1---C8---F3      107.31 (17)
  C7---N3---C5---C6   0.9 (2)        C2---C1---C8---F3      −70.9 (2)
  C7---N3---C5---N2   −177.66 (11)                          
  ------------------- -------------- ---------------------- --------------

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