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

For applications of 1,2,3-triazole and its derivatives, see: Danoun *et al.* (1998[@bb2]); Manfredini *et al.* (2000[@bb3]).

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~8~H~9~N~5~O~2~*M* *~r~* = 207.20Monoclinic,*a* = 15.4576 (6) Å*b* = 16.0945 (9) Å*c* = 7.5348 (3) Åβ = 90.079 (4)°*V* = 1874.52 (15) Å^3^*Z* = 8Mo *K*α radiationμ = 0.11 mm^−1^*T* = 293 K0.15 × 0.12 × 0.10 mm

### Data collection   {#sec2.1.2}

Bruker MWPC area-detector diffractometer5457 measured reflections3247 independent reflections2312 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.014

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.053*wR*(*F* ^2^) = 0.153*S* = 1.083247 reflections275 parametersH-atom parameters constrainedΔρ~max~ = 0.19 e Å^−3^Δρ~min~ = −0.21 e Å^−3^

 {#d5e412}

Data collection: *FRAMBO* (Bruker, 2004[@bb1]); cell refinement: *SAINT* (Bruker, 2004[@bb1]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXTL* (Sheldrick, 2008[@bb4]); 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, New_Global_Publ_Block. DOI: [10.1107/S1600536814012380/xu5793sup1.cif](http://dx.doi.org/10.1107/S1600536814012380/xu5793sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536814012380/xu5793Isup2.hkl](http://dx.doi.org/10.1107/S1600536814012380/xu5793Isup2.hkl)

CCDC reference: [1005571](http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1005571)

Additional supporting information: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?xu5793&file=xu5793sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?xu5793sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?xu5793&checkcif=yes)

Supporting information for this paper is available from the IUCr electronic archives (Reference: [XU5793](http://scripts.iucr.org/cgi-bin/sendsup?xu5793)).

We are grateful for financial support from the National Natural Science Foundation of China (No. 81302644) and Jiangsu Ainaji Neo Energy Science & Technology Co. Ltd (No. 8507040091).

S1. Comment {#comment}
===========

1,2,3-Triazole and its derivatives had attracted considerable attention for the past few decades due to their chemotherapeutical value. Many 1,2,3-triazoles are found to be potent antimicrobial and antiviral agents. Some of them have exhibited antiproliferative and anticancer activities (Danoun *et al.*, 1998). Some 1,2,3-triazoles are used as DNA cleaving agents (Manfredini *et al.*, 2000) and potassium channel activators. Prompted by the chemotherapeutic importance of 1,2,3-triazoles and its derivatives, we have synthesized the title compound and report its crystal structure herein.

The title compound, contains two crystallographically independent molecules and bond lengths and angles are in the normal range(Fig. 1). The dihedral angle between the triazole and pyrazole rings is 4.80 (14)° and 8.45 (16)° respectively. The crystal structure is stabilized by N--H···N hydrogen bonds linking molecules into one-dimensional chains running parallel to the *b* axis (Fig. 2). The structure is further stabilized by π···π stacking interactions, with centroid-to-centroid separations of 3.8001 (15)--3.8421 (15) Å.

S2. Experimental {#experimental}
================

3-Azido-1*H*-pyrazole (20 mmol) was treated with ethyl acetoacetate (24 mmol) in methanol (75 ml) and the mixture was cooled to 273 K. Sodium methoxide (24 mmol) was added to the above mixture and stirred at ambient temperature for 24 h. After completion of the reaction, the mixture was poured on to ice cold water. The precipitated solid was filtered, washed with water and recrystallized from methanol, then 5-methyl-1-(1*H*-pyrazol-3-yl)-1*H*-1,2,3-triazole-4- carboxylic acid were obtained. A mixture of 5-methyl-1-(1*H*-pyrazol-3-yl)-1*H*-1,2,3-triazole-4- carboxylic acid (0.1 mmol) and Et~3~N(0.2 mmol) in methanol (15 ml) was stirred at room temperature until the starting material disappeared. The resulting mixture was filtered and let the filtrate still for 24 h, colorless needle-like crystals were obtained.

S3. Refinement {#refinement}
==============

H-atoms were placed in calculated positions and refined constrained to ride on their parent atoms, with C---H = 0.93---0.96 Å and N---H = 0.86 Å, *U*~iso~(H) = 1.5*U*~eq~(C) for methyl H atoms and 1.2U~eq~(C,N) for the others.

Figures
=======

![The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.](e-70-0o755-fig1){#Fap1}

![View of the one-dimensional chains of the title compound extending along the b axis. All the hydrogen atoms except those involved in hydrogen bonding have been omitted for clarity. Hydrogen bonds are shown as dashed lines.](e-70-0o755-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~8~H~9~N~5~O~2~          *F*(000) = 864
  *M~r~* = 207.20           *D*~x~ = 1.468 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ybc      Cell parameters from 1802 reflections
  *a* = 15.4576 (6) Å       θ = 3.2--28.8°
  *b* = 16.0945 (9) Å       µ = 0.11 mm^−1^
  *c* = 7.5348 (3) Å        *T* = 293 K
  β = 90.079 (4)°           Needle, colorless
  *V* = 1874.52 (15) Å^3^   0.15 × 0.12 × 0.10 mm
  *Z* = 8                   
  ------------------------- ---------------------------------------

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

  ------------------------------------------ --------------------------------------
  Bruker MWPC area-detector diffractometer   2312 reflections with *I* \> 2σ(*I*)
  Radiation source: fine-focus sealed tube   *R*~int~ = 0.014
  Graphite monochromator                     θ~max~ = 25.2°, θ~min~ = 2.9°
  Detector resolution: 0 pixels mm^-1^       *h* = −18→18
  phi and ω scans                            *k* = −13→19
  5457 measured reflections                  *l* = −9→8
  3247 independent 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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.053   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.153                  H-atom parameters constrained
  *S* = 1.08                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0605*P*)^2^ + 0.760*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  3247 reflections                      (Δ/σ)~max~ = 0.001
  275 parameters                        Δρ~max~ = 0.19 e Å^−3^
  0 restraints                          Δρ~min~ = −0.21 e Å^−3^
  ------------------------------------- ------------------------------------------------------------------------------------------------

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

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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~   
  N1     0.02649 (13)    0.54949 (11)   0.2168 (3)    0.0420 (5)           
  N2     −0.00324 (14)   0.62920 (13)   0.2245 (3)    0.0541 (6)           
  N3     0.05838 (14)    0.67707 (13)   0.1660 (3)    0.0543 (6)           
  N4     −0.07242 (14)   0.36437 (14)   0.3301 (3)    0.0537 (6)           
  H4N    −0.0746         0.3111         0.3380        0.064\*              
  N5     −0.00456 (14)   0.40638 (13)   0.2603 (3)    0.0530 (6)           
  N6     0.46882 (13)    0.32571 (12)   0.7645 (3)    0.0439 (5)           
  N7     0.49447 (14)    0.24550 (13)   0.7423 (3)    0.0526 (6)           
  N8     0.43181 (14)    0.19849 (13)   0.7993 (3)    0.0497 (6)           
  N9     0.57547 (15)    0.50986 (14)   0.6752 (3)    0.0583 (6)           
  H9N    0.5810          0.5630         0.6799        0.070\*              
  N10    0.50816 (15)    0.46815 (13)   0.7472 (3)    0.0573 (6)           
  O1     0.21506 (14)    0.74272 (12)   0.0353 (3)    0.0738 (7)           
  O2     0.26259 (12)    0.61387 (11)   −0.0124 (3)   0.0578 (5)           
  O3     0.27863 (13)    0.13456 (11)   0.9465 (3)    0.0632 (6)           
  O4     0.22679 (11)    0.26408 (11)   0.9707 (3)    0.0539 (5)           
  C1     −0.02877 (16)   0.48505 (14)   0.2760 (3)    0.0418 (6)           
  C2     0.12793 (16)    0.62903 (15)   0.1203 (3)    0.0437 (6)           
  C3     0.10864 (15)    0.54705 (14)   0.1526 (3)    0.0404 (6)           
  C4     −0.13523 (18)   0.41433 (17)   0.3852 (4)    0.0551 (7)           
  H4     −0.1872         0.3978         0.4365        0.066\*              
  C5     0.20503 (17)    0.66914 (16)   0.0457 (4)    0.0480 (6)           
  C6     −0.11000 (18)   0.49401 (16)   0.3534 (4)    0.0543 (7)           
  H6     −0.1399         0.5428         0.3775        0.065\*              
  C7     0.15978 (18)    0.46989 (16)   0.1315 (4)    0.0597 (8)           
  H7A    0.1607          0.4401         0.2419        0.090\*              
  H7B    0.2179          0.4837         0.0976        0.090\*              
  H7C    0.1339          0.4358         0.0414        0.090\*              
  C8     0.33943 (19)    0.64841 (19)   −0.0931 (5)   0.0678 (9)           
  H8A    0.3235          0.6797         −0.1966       0.102\*              
  H8B    0.3778          0.6042         −0.1265       0.102\*              
  H8C    0.3680          0.6843         −0.0098       0.102\*              
  C9     0.52627 (17)    0.38975 (15)   0.7090 (3)    0.0450 (6)           
  C10    0.36599 (16)    0.24783 (15)   0.8580 (3)    0.0414 (6)           
  C11    0.38853 (16)    0.32974 (14)   0.8365 (3)    0.0429 (6)           
  C12    0.28750 (17)    0.20845 (16)   0.9289 (3)    0.0449 (6)           
  C13    0.6320 (2)      0.46024 (18)   0.5970 (4)    0.0648 (8)           
  H13    0.6826          0.4764         0.5399        0.078\*              
  C14    0.6020 (2)      0.38078 (18)   0.6156 (4)    0.0655 (8)           
  H14    0.6271          0.3319         0.5746        0.079\*              
  C15    0.14627 (18)    0.23064 (18)   1.0380 (4)    0.0608 (8)           
  H15A   0.1207          0.1951         0.9500        0.091\*              
  H15B   0.1074          0.2754         1.0646        0.091\*              
  H15C   0.1574          0.1992         1.1438        0.091\*              
  C16    0.3426 (2)      0.40823 (17)   0.8776 (5)    0.0707 (9)           
  H16A   0.3720          0.4365         0.9724        0.106\*              
  H16B   0.2844          0.3960         0.9130        0.106\*              
  H16C   0.3418          0.4430         0.7742        0.106\*              
  ------ --------------- -------------- ------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  N1    0.0437 (11)   0.0246 (11)   0.0577 (13)   0.0050 (9)     0.0077 (10)    −0.0008 (9)
  N2    0.0512 (13)   0.0265 (11)   0.0846 (16)   0.0056 (10)    0.0190 (12)    0.0008 (11)
  N3    0.0536 (13)   0.0297 (12)   0.0797 (16)   0.0022 (10)    0.0166 (12)    0.0000 (11)
  N4    0.0569 (14)   0.0294 (12)   0.0749 (15)   −0.0065 (11)   0.0073 (12)    0.0048 (11)
  N5    0.0510 (12)   0.0304 (12)   0.0775 (16)   −0.0007 (10)   0.0115 (11)    0.0028 (11)
  N6    0.0485 (12)   0.0262 (11)   0.0569 (13)   0.0037 (9)     0.0037 (10)    −0.0012 (9)
  N7    0.0490 (13)   0.0283 (12)   0.0806 (16)   0.0044 (10)    0.0112 (11)    −0.0007 (11)
  N8    0.0476 (12)   0.0287 (11)   0.0729 (15)   0.0046 (10)    0.0064 (11)    0.0003 (10)
  N9    0.0654 (15)   0.0321 (12)   0.0774 (16)   −0.0088 (11)   0.0060 (13)    0.0001 (11)
  N10   0.0628 (14)   0.0295 (12)   0.0797 (16)   −0.0052 (11)   0.0098 (13)    −0.0016 (11)
  O1    0.0751 (14)   0.0326 (11)   0.1139 (18)   −0.0044 (10)   0.0299 (13)    0.0005 (11)
  O2    0.0488 (11)   0.0380 (11)   0.0865 (14)   −0.0008 (9)    0.0176 (10)    0.0030 (9)
  O3    0.0636 (12)   0.0309 (10)   0.0953 (15)   −0.0041 (9)    0.0127 (11)    0.0010 (10)
  O4    0.0461 (10)   0.0376 (10)   0.0780 (13)   0.0013 (8)     0.0139 (9)     0.0032 (9)
  C1    0.0461 (14)   0.0291 (13)   0.0502 (14)   −0.0016 (11)   0.0014 (11)    −0.0004 (11)
  C2    0.0452 (14)   0.0308 (13)   0.0552 (15)   0.0034 (11)    0.0046 (12)    −0.0029 (11)
  C3    0.0443 (13)   0.0293 (13)   0.0477 (14)   0.0044 (11)    0.0051 (11)    0.0002 (11)
  C4    0.0481 (15)   0.0448 (16)   0.0724 (19)   −0.0039 (13)   0.0119 (14)    −0.0014 (14)
  C5    0.0517 (15)   0.0316 (14)   0.0608 (16)   0.0005 (12)    0.0060 (13)    −0.0007 (12)
  C6    0.0529 (15)   0.0351 (15)   0.0750 (19)   0.0016 (13)    0.0137 (14)    −0.0020 (13)
  C7    0.0509 (15)   0.0355 (15)   0.093 (2)     0.0072 (13)    0.0223 (15)    0.0047 (14)
  C8    0.0522 (16)   0.0539 (19)   0.097 (2)     −0.0017 (15)   0.0252 (16)    0.0082 (17)
  C9    0.0488 (15)   0.0295 (14)   0.0569 (16)   −0.0011 (11)   0.0011 (12)    0.0016 (11)
  C10   0.0449 (13)   0.0299 (13)   0.0496 (15)   0.0036 (11)    0.0013 (11)    −0.0025 (11)
  C11   0.0466 (14)   0.0277 (13)   0.0543 (15)   0.0027 (11)    0.0050 (11)    −0.0023 (11)
  C12   0.0494 (15)   0.0340 (14)   0.0511 (15)   0.0001 (12)    −0.0010 (12)   0.0000 (12)
  C13   0.0654 (18)   0.0450 (18)   0.084 (2)     −0.0062 (15)   0.0177 (16)    0.0031 (15)
  C14   0.0701 (19)   0.0386 (16)   0.088 (2)     0.0007 (14)    0.0264 (17)    −0.0005 (15)
  C15   0.0483 (16)   0.0502 (18)   0.084 (2)     −0.0022 (13)   0.0157 (15)    0.0002 (15)
  C16   0.0689 (19)   0.0316 (15)   0.112 (3)     0.0045 (14)    0.0308 (18)    −0.0092 (16)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

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

  ---------------- ------------- ------------------- -----------
  N1---C3          1.360 (3)     C2---C3             1.374 (3)
  N1---N2          1.364 (3)     C2---C5             1.468 (4)
  N1---C1          1.416 (3)     C3---C7             1.481 (3)
  N2---N3          1.302 (3)     C4---C6             1.362 (4)
  N3---C2          1.369 (3)     C4---H4             0.9300
  N4---C4          1.328 (3)     C6---H6             0.9300
  N4---N5          1.355 (3)     C7---H7A            0.9600
  N4---H4N         0.8600        C7---H7B            0.9600
  N5---C1          1.326 (3)     C7---H7C            0.9600
  N6---C11         1.357 (3)     C8---H8A            0.9600
  N6---N7          1.361 (3)     C8---H8B            0.9600
  N6---C9          1.424 (3)     C8---H8C            0.9600
  N7---N8          1.302 (3)     C9---C14            1.375 (4)
  N8---C10         1.365 (3)     C10---C11           1.373 (3)
  N9---C13         1.323 (4)     C10---C12           1.470 (4)
  N9---N10         1.352 (3)     C11---C16           1.482 (3)
  N9---H9N         0.8600        C13---C14           1.368 (4)
  N10---C9         1.324 (3)     C13---H13           0.9300
  O1---C5          1.197 (3)     C14---H14           0.9300
  O2---C5          1.333 (3)     C15---H15A          0.9600
  O2---C8          1.446 (3)     C15---H15B          0.9600
  O3---C12         1.204 (3)     C15---H15C          0.9600
  O4---C12         1.335 (3)     C16---H16A          0.9600
  O4---C15         1.448 (3)     C16---H16B          0.9600
  C1---C6          1.392 (4)     C16---H16C          0.9600
                                                     
  C3---N1---N2     110.93 (19)   H7A---C7---H7B      109.5
  C3---N1---C1     130.9 (2)     C3---C7---H7C       109.5
  N2---N1---C1     118.16 (19)   H7A---C7---H7C      109.5
  N3---N2---N1     107.18 (19)   H7B---C7---H7C      109.5
  N2---N3---C2     109.0 (2)     O2---C8---H8A       109.5
  C4---N4---N5     112.7 (2)     O2---C8---H8B       109.5
  C4---N4---H4N    123.6         H8A---C8---H8B      109.5
  N5---N4---H4N    123.6         O2---C8---H8C       109.5
  C1---N5---N4     102.9 (2)     H8A---C8---H8C      109.5
  C11---N6---N7    111.2 (2)     H8B---C8---H8C      109.5
  C11---N6---C9    130.9 (2)     N10---C9---C14      113.1 (2)
  N7---N6---C9     118.0 (2)     N10---C9---N6       119.6 (2)
  N8---N7---N6     107.08 (19)   C14---C9---N6       127.3 (2)
  N7---N8---C10    108.9 (2)     N8---C10---C11      109.3 (2)
  C13---N9---N10   112.8 (2)     N8---C10---C12      118.9 (2)
  C13---N9---H9N   123.6         C11---C10---C12     131.8 (2)
  N10---N9---H9N   123.6         N6---C11---C10      103.5 (2)
  C9---N10---N9    102.9 (2)     N6---C11---C16      124.3 (2)
  C5---O2---C8     115.5 (2)     C10---C11---C16     132.2 (2)
  C12---O4---C15   116.0 (2)     O3---C12---O4       123.8 (2)
  N5---C1---C6     113.0 (2)     O3---C12---C10      124.1 (2)
  N5---C1---N1     120.0 (2)     O4---C12---C10      112.2 (2)
  C6---C1---N1     126.9 (2)     N9---C13---C14      107.1 (3)
  N3---C2---C3     109.1 (2)     N9---C13---H13      126.4
  N3---C2---C5     119.1 (2)     C14---C13---H13     126.4
  C3---C2---C5     131.8 (2)     C13---C14---C9      104.1 (3)
  N1---C3---C2     103.8 (2)     C13---C14---H14     128.0
  N1---C3---C7     124.1 (2)     C9---C14---H14      128.0
  C2---C3---C7     132.1 (2)     O4---C15---H15A     109.5
  N4---C4---C6     107.8 (2)     O4---C15---H15B     109.5
  N4---C4---H4     126.1         H15A---C15---H15B   109.5
  C6---C4---H4     126.1         O4---C15---H15C     109.5
  O1---C5---O2     123.5 (3)     H15A---C15---H15C   109.5
  O1---C5---C2     124.4 (2)     H15B---C15---H15C   109.5
  O2---C5---C2     112.0 (2)     C11---C16---H16A    109.5
  C4---C6---C1     103.6 (2)     C11---C16---H16B    109.5
  C4---C6---H6     128.2         H16A---C16---H16B   109.5
  C1---C6---H6     128.2         C11---C16---H16C    109.5
  C3---C7---H7A    109.5         H16A---C16---H16C   109.5
  C3---C7---H7B    109.5         H16B---C16---H16C   109.5
  ---------------- ------------- ------------------- -----------

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

  --------------------- --------- --------- ----------- ---------------
  *D*---H···*A*         *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  N4---H4*N*···N3^i^    0.86      2.17      3.022 (3)   170
  N9---H9*N*···N8^ii^   0.86      2.20      3.044 (3)   169
  --------------------- --------- --------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*         *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  ------------------- --------- ------- ----------- -------------
  N4---H4*N*⋯N3^i^    0.86      2.17    3.022 (3)   170
  N9---H9*N*⋯N8^ii^   0.86      2.20    3.044 (3)   169

Symmetry codes: (i) ; (ii) .
