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

For general background to the title compound, see: Rivera *et al.* (2010[@bb6]). For related structures, see: Rivera *et al.* (2010[@bb6], 2011[@bb5]); Silversides *et al.* (2006[@bb7]).

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~10~H~10~N~4~*M* *~r~* = 186.2Orthorhombic,*a* = 7.6404 (3) Å*b* = 15.1703 (7) Å*c* = 15.9168 (7) Å*V* = 1844.87 (14) Å^3^*Z* = 8Cu *K*α radiationμ = 0.69 mm^−1^*T* = 120 K0.17 × 0.15 × 0.10 mm

### Data collection   {#sec2.1.2}

Agilent Xcalibur (Atlas, Gemini ultra) diffractometerAbsorption correction: multi-scan (*CrysAlis PRO*; Agilent, 2012[@bb1]) *T* ~min~ = 0.68, *T* ~max~ = 19893 measured reflections1641 independent reflections1359 reflections with *I* \> 3σ(*I*)*R* ~int~ = 0.061

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.039*wR*(*F* ^2^) = 0.104*S* = 1.551641 reflections133 parametersH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 0.16 e Å^−3^Δρ~min~ = −0.20 e Å^−3^

 {#d5e449}

Data collection: *CrysAlis PRO* (Agilent, 2012[@bb1]); cell refinement: *CrysAlis PRO*; data reduction: *CrysAlis PRO*; program(s) used to solve structure: *SUPERFLIP* (Palatinus & Chapuis, 2007[@bb3]); program(s) used to refine structure: *JANA2006* (Petříček *et al.*, 2006[@bb4]); molecular graphics: *DIAMOND* (Brandenburg & Putz, 2005[@bb2]); software used to prepare material for publication: *JANA2006*.

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

###### 

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: [10.1107/S1600536812047538/bt6866sup1.cif](http://dx.doi.org/10.1107/S1600536812047538/bt6866sup1.cif)

###### 

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536812047538/bt6866Isup2.hkl](http://dx.doi.org/10.1107/S1600536812047538/bt6866Isup2.hkl)

###### 

Click here for additional data file.

Supplementary material file. DOI: [10.1107/S1600536812047538/bt6866Isup3.cml](http://dx.doi.org/10.1107/S1600536812047538/bt6866Isup3.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?bt6866&file=bt6866sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?bt6866sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?bt6866&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [BT6866](http://scripts.iucr.org/cgi-bin/sendsup?bt6866)).

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work, as well the Praemium Academiae project of the Academy of Sciences of the Czech Republic. LJ---C acknowledges the Vicerrectoría Académica de la Universidad Nacional de Colombia for a fellowship.

Comment
=======

The reaction of *N*^1^,*N*^2^-bis((1*H*-benzotriazol-1-yl)methyl)benzene-1,2-diamine with potassium cyanide in DMSO at room temperature gives the title compound in high yield. The two cyanomethyl groups are both *anti* with respect to the planar aromatic ring, no doubt in order to favour intermolecular N---H···N interactions. Intermolecular amine-to-amine and amine-to-cyano hydrogen bonding interactions established \"ladder-like\" parallel tapes in the crystalline solid (Fig. 2).

The molecular structure and atom numbering scheme for the title compound are shown in Fig. 1. Its X-ray structure confirms the presence of intramolecular hydrogen bond between the amino groups \[N--H, 2.426 (18) Å\]. Furthermore the observed C3---N1 bond length \[1.4357 (17) Å\] is considerably elongated in relation to related structures \[1.404 (3) Å\] (Rivera *et al.*, 2010), \[1.3961 (18) Å\] (Silversides *et al.*, 2006) and is longer than the C4---N2 bond \[1.4016 (16) Å\]. Thus, these results indicate that the intramolecular interaction is responsible for the C3---N1 bond elongation. This is confirmed by the N1---C7 bond length \[1.4648 (18) Å\] that is longer than N2---C5 bond \[1.4457 (19) Å\]. Besides, the hybridization of both N1 and N2 atoms are slightly different. In fact, N1 has more *sp^2^* character \[Sα = 347.25°\] than N2 \[Sα = 330.39°\] if compared to *sp^3^*-hybridization \[Sα = 328.50°\] angle value. Other bond distances and bond angles are in good agreement with the standard values.

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

A mixture of potassium cyanide (0.260 g, 4.00 mmol) and *N*^1^,*N*^2^-bis((1*H*-benzotriazol-1-yl)methyl)benzene-1,2-diamine (0.370 g, 1.00 mmol) was stirred at room temperature in DMSO (5 ml) for 6 h. After quenching by addition of aqueous ammonium chloride a solid formed which was separated and extracted with ethyl acetate.The organic extract was sequentially washed with saturated Na~2~CO~3~ solution and water, then dried (Na~2~SO~4~), filtered, and concentrated to give a solid homogeneous by TLC (80% EtOAc/benzene) in 82% yield. Single crystals were obtained by recrystallization from chloroform/methanol by slow evaporation of the solvent at room temperaature, m.p. 399--400 K.

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

All hydrogen atoms were discernible in difference Fourier maps and could be refined to reasonable geometry, but according to common practice H atoms bonded to C were kept in ideal positions with C--H = 0.96 Å. The coordinates of the amino H atoms were refined. *U*~iso~(H) was set to 1.2*U*~eq~(C,N). All non-hydrogen atoms were refined using harmonic refinement.

Figures
=======

![A view of the crystal structure of the tittle compund (I) with the numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.](e-68-o3429-fig1){#Fap1}

![Packing of the molecules of the title compound view along a axis. N---H···CN and N---H···N hydrogen bonds are drawn as dashed lines.](e-68-o3429-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~10~H~10~N~4~            *D*~x~ = 1.341 Mg m^−3^
  *M~r~* = 186.2            Melting point: 399 K
  Orthorhombic, *Pbca*      Cu *K*α radiation, λ = 1.5418 Å
  Hall symbol: -P 2ac 2ab   Cell parameters from 4237 reflections
  *a* = 7.6404 (3) Å        θ = 4.0--67.0°
  *b* = 15.1703 (7) Å       µ = 0.69 mm^−1^
  *c* = 15.9168 (7) Å       *T* = 120 K
  *V* = 1844.87 (14) Å^3^   Polygon shape, white
  *Z* = 8                   0.17 × 0.15 × 0.10 mm
  *F*(000) = 784            
  ------------------------- ---------------------------------------

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

  ------------------------------------------------------------------- --------------------------------------
  Agilent Xcalibur (Atlas, Gemini ultra) diffractometer               1641 independent reflections
  Radiation source: Enhance Ultra (Cu) X-ray Source                   1359 reflections with *I* \> 3σ(*I*)
  Mirror monochromator                                                *R*~int~ = 0.061
  Detector resolution: 10.3784 pixels mm^-1^                          θ~max~ = 67.2°, θ~min~ = 5.6°
  ω scans                                                             *h* = −7→9
  Absorption correction: multi-scan (*CrysAlis PRO*; Agilent, 2012)   *k* = −18→18
  *T*~min~ = 0.68, *T*~max~ = 1                                       *l* = −18→16
  9893 measured reflections                                           
  ------------------------------------------------------------------- --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------
  Refinement on *F*^2^                  34 constraints
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.039   H atoms treated by a mixture of independent and constrained refinement
  *wR*(*F*^2^) = 0.104                  Weighting scheme based on measured s.u.\'s *w* = 1/(σ^2^(*I*) + 0.0016*I*^2^)
  *S* = 1.55                            (Δ/σ)~max~ = 0.005
  1641 reflections                      Δρ~max~ = 0.16 e Å^−3^
  133 parameters                        Δρ~min~ = −0.20 e Å^−3^
  0 restraints                          
  ------------------------------------- -------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Refinement. The refinement was carried out against all reflections. The conventional *R*-factor is always based on *F*. The goodness of fit as well as the weighted *R*-factor are based on *F* and *F*^2^ for refinement carried out on *F* and *F*^2^, respectively. The threshold expression is used only for calculating *R*-factors *etc*. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see \_refine_ls_weighting_details, that does not force *S* to be one. Therefore the values of *S* are usually larger than the ones from the *SHELX* program.
  ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------- -------------- -------------- --------------- -------------------- --
          *x*            *y*            *z*             *U*~iso~\*/*U*~eq~   
  N1      0.67776 (14)   0.46314 (7)    0.09105 (8)     0.0197 (3)           
  N2      0.59009 (13)   0.37473 (8)    −0.05397 (8)    0.0182 (3)           
  N3      0.75959 (16)   0.31452 (9)    0.25065 (9)     0.0316 (4)           
  N4      0.68740 (17)   0.42625 (9)    −0.25896 (9)    0.0314 (4)           
  C1      0.67383 (17)   0.35295 (9)    0.20428 (10)    0.0228 (4)           
  C2      0.62292 (17)   0.38628 (9)    −0.20642 (10)   0.0227 (4)           
  C3      0.81190 (16)   0.41747 (8)    0.04529 (9)     0.0179 (4)           
  C4      0.76583 (16)   0.37282 (8)    −0.02878 (9)    0.0176 (4)           
  C5      0.54231 (16)   0.33892 (9)    −0.13496 (9)    0.0200 (4)           
  C6      0.89448 (16)   0.32671 (9)    −0.07229 (10)   0.0203 (4)           
  C7      0.57084 (17)   0.40361 (9)    0.14220 (10)    0.0215 (4)           
  C8      1.11225 (17)   0.37219 (9)    0.02841 (11)    0.0248 (4)           
  C9      0.98466 (17)   0.41713 (9)    0.07282 (10)    0.0224 (4)           
  C10     1.06689 (17)   0.32645 (10)   −0.04320 (10)   0.0238 (4)           
  H1c5    0.417265       0.339719       −0.140823       0.024\*              
  H2c5    0.57431        0.277778       −0.137292       0.024\*              
  H1c6    0.864639       0.294979       −0.122465       0.0244\*             
  H1c7    0.508788       0.363609       0.106188        0.0258\*             
  H2c7    0.481985       0.436862       0.17073         0.0258\*             
  H1c8    1.23154        0.372856       0.047341        0.0298\*             
  H1c9    1.015681       0.44837        0.123117        0.0268\*             
  H1c10   1.154716       0.294105       −0.073369       0.0286\*             
  H1      0.732 (2)      0.5050 (12)    0.1255 (12)     0.0237\*             
  H2      0.536 (2)      0.4245 (12)    −0.0403 (12)    0.0219\*             
  ------- -------------- -------------- --------------- -------------------- --

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

  ----- ------------ ------------ ------------ ------------- ------------- -------------
        *U*^11^      *U*^22^      *U*^33^      *U*^12^       *U*^13^       *U*^23^
  N1    0.0140 (5)   0.0231 (6)   0.0221 (7)   0.0001 (4)    −0.0013 (5)   −0.0013 (5)
  N2    0.0087 (5)   0.0257 (6)   0.0202 (7)   0.0023 (4)    0.0000 (5)    −0.0013 (5)
  N3    0.0229 (6)   0.0399 (7)   0.0319 (8)   −0.0047 (6)   −0.0020 (6)   0.0091 (6)
  N4    0.0267 (6)   0.0389 (7)   0.0287 (8)   0.0053 (6)    0.0054 (6)    0.0065 (6)
  C1    0.0167 (7)   0.0287 (7)   0.0231 (8)   −0.0035 (6)   0.0041 (6)    −0.0004 (6)
  C2    0.0154 (6)   0.0286 (7)   0.0241 (9)   0.0052 (6)    −0.0007 (6)   −0.0013 (6)
  C3    0.0117 (6)   0.0210 (6)   0.0210 (8)   −0.0002 (5)   0.0014 (5)    0.0041 (5)
  C4    0.0101 (6)   0.0217 (6)   0.0211 (8)   −0.0006 (5)   0.0001 (5)    0.0045 (5)
  C5    0.0124 (6)   0.0268 (7)   0.0208 (8)   −0.0011 (5)   −0.0006 (6)   0.0008 (5)
  C6    0.0131 (6)   0.0249 (7)   0.0229 (8)   0.0011 (5)    0.0019 (6)    0.0012 (6)
  C7    0.0137 (6)   0.0285 (7)   0.0223 (8)   0.0013 (5)    0.0007 (6)    −0.0007 (6)
  C8    0.0094 (6)   0.0300 (7)   0.0350 (9)   −0.0019 (5)   −0.0030 (6)   0.0081 (6)
  C9    0.0153 (6)   0.0262 (7)   0.0256 (9)   −0.0038 (5)   −0.0042 (6)   0.0051 (6)
  C10   0.0107 (6)   0.0284 (7)   0.0324 (9)   0.0028 (5)    0.0043 (6)    0.0064 (6)
  ----- ------------ ------------ ------------ ------------- ------------- -------------

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

  ---------------- ------------- ------------------ -------------
  N1---C3          1.4357 (17)   C4---C6            1.3911 (19)
  N1---C7          1.4648 (18)   C5---H1c5          0.96
  N1---H1          0.935 (18)    C5---H2c5          0.96
  N2---C4          1.4016 (16)   C6---C10           1.3963 (18)
  N2---C5          1.4457 (19)   C6---H1c6          0.96
  N2---H2          0.889 (18)    C7---H1c7          0.96
  N3---C1          1.146 (2)     C7---H2c7          0.96
  N4---C2          1.144 (2)     C8---C9            1.384 (2)
  C1---C7          1.479 (2)     C8---C10           1.379 (2)
  C2---C5          1.480 (2)     C8---H1c8          0.96
  C3---C4          1.404 (2)     C9---H1c9          0.96
  C3---C9          1.3908 (18)   C10---H1c10        0.96
                                                    
  C3---N1---C7     112.49 (10)   H1c5---C5---H2c5   105.18
  C3---N1---H1     108.1 (10)    C4---C6---C10      120.20 (14)
  C7---N1---H1     109.8 (11)    C4---C6---H1c6     119.9
  C4---N2---C5     119.29 (11)   C10---C6---H1c6    119.9
  C4---N2---H2     113.2 (11)    N1---C7---C1       113.27 (11)
  C5---N2---H2     114.8 (12)    N1---C7---H1c7     109.47
  N3---C1---C7     177.27 (15)   N1---C7---H2c7     109.47
  N4---C2---C5     176.55 (16)   C1---C7---H1c7     109.47
  N1---C3---C4     118.67 (11)   C1---C7---H2c7     109.47
  N1---C3---C9     121.29 (13)   H1c7---C7---H2c7   105.38
  C4---C3---C9     120.04 (12)   C9---C8---C10      119.55 (13)
  N2---C4---C3     118.05 (12)   C9---C8---H1c8     120.22
  N2---C4---C6     123.02 (13)   C10---C8---H1c8    120.22
  C3---C4---C6     118.90 (12)   C3---C9---C8       120.63 (14)
  N2---C5---C2     113.45 (11)   C3---C9---H1c9     119.69
  N2---C5---H1c5   109.47        C8---C9---H1c9     119.69
  N2---C5---H2c5   109.47        C6---C10---C8      120.65 (13)
  C2---C5---H1c5   109.47        C6---C10---H1c10   119.67
  C2---C5---H2c5   109.47        C8---C10---H1c10   119.67
  ---------------- ------------- ------------------ -------------

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

  ------------------ ------------ ------------ ------------- ---------------
  *D*---H···*A*      *D*---H      H···*A*      *D*···*A*     *D*---H···*A*
  N1---H1···N4^i^    0.935 (18)   2.202 (19)   3.0946 (19)   159.2 (16)
  N2---H2···N1       0.889 (18)   2.427 (18)   2.7524 (18)   102.0 (13)
  N2---H2···N1^ii^   0.889 (18)   2.494 (17)   3.2536 (16)   143.8 (15)
  ------------------ ------------ ------------ ------------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*      *D*---H      H⋯*A*        *D*⋯*A*       *D*---H⋯*A*
  ---------------- ------------ ------------ ------------- -------------
  N1---H1⋯N4^i^    0.935 (18)   2.202 (19)   3.0946 (19)   159.2 (16)
  N2---H2⋯N1       0.889 (18)   2.427 (18)   2.7524 (18)   102.0 (13)
  N2---H2⋯N1^ii^   0.889 (18)   2.494 (17)   3.2536 (16)   143.8 (15)

Symmetry codes: (i) ; (ii) .
