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The title compound, C7H5N5, was designed and synthesized as a potential anti­tumour agent. The mol­ecules are located on crystallographic mirror planes. The electron-accepting 6-cyano group has no effect on the π-electron cloud of the heterocyclic system. The mol­ecular packing is governed by C—H...N inter­molecular hydrogen bonds, which link the mol­ecules into chains running along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007240/ci2013sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007240/ci2013Isup2.hkl
Contains datablock I

CCDC reference: 605013

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.053
  • wR factor = 0.147
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C6 - C10 ... 1.44 Ang. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: The six authors in the present work were involved in the following activities. Synthesis of the compound (P.\<C. & V.M.), preparation of the suitable crystals by a special (vapour diffusion) technique (S.K.), measurement of the data and searching of the CSD (F.G.), solution and refinement of the structure, evaluation of the literature data and preparation of the article (text + figures, J.L. & V.K.).

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: XSCANS (Siemens, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON92 (Spek, 1992); software used to prepare material for publication: SHELXL97.

5-Methyl-1,2,4-triazolo[1,5-a]pyrimidine-6-carbonitrile top
Crystal data top
C7H5N5F(000) = 164
Mr = 159.16Dx = 1.427 Mg m3
Monoclinic, P21/mMelting point: 418 K
Hall symbol: -P 2ybMo Kα radiation, λ = 0.71073 Å
a = 7.105 (2) ÅCell parameters from 20 reflections
b = 6.413 (2) Åθ = 7–20°
c = 8.190 (3) ŵ = 0.10 mm1
β = 96.82 (3)°T = 296 K
V = 370.5 (2) Å3Prism, orange
Z = 20.30 × 0.20 × 0.15 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.040
Radiation source: fine-focus sealed tubeθmax = 30.0°, θmin = 2.5°
Graphite monochromatorh = 19
ω/2θ scansk = 19
1628 measured reflectionsl = 1111
1165 independent reflections3 standard reflections every 97 reflections
723 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0688P)2 + 0.0536P]
where P = (Fo2 + 2Fc2)/3
1165 reflections(Δ/σ)max = 0.001
80 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.24 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3528 (4)0.25000.6871 (2)0.0569 (6)
C20.5230 (4)0.25000.6295 (3)0.0548 (7)
H20.63530.25000.70060.066*
N30.5243 (3)0.25000.4680 (2)0.0460 (5)
N40.3342 (2)0.25000.4157 (2)0.0354 (4)
C50.2534 (3)0.25000.2566 (3)0.0369 (5)
C60.0589 (3)0.25000.2396 (3)0.0420 (6)
C70.0394 (4)0.25000.3799 (3)0.0508 (6)
H70.17120.25000.36270.061*
N80.0410 (3)0.25000.5318 (3)0.0524 (6)
C8A0.2329 (4)0.25000.5508 (3)0.0424 (6)
C90.3792 (4)0.25000.1248 (3)0.0541 (7)
H9A0.307 (4)0.25000.019 (4)0.068 (9)*
H9B0.462 (4)0.125 (4)0.136 (3)0.107 (9)*
C100.0494 (4)0.25000.0799 (3)0.0542 (7)
N100.1435 (4)0.25000.0423 (3)0.0804 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0785 (17)0.0606 (14)0.0297 (10)0.0000.0018 (10)0.000
C20.0581 (16)0.0543 (15)0.0458 (13)0.0000.0198 (12)0.000
N30.0365 (10)0.0552 (12)0.0425 (11)0.0000.0109 (8)0.000
N40.0336 (9)0.0414 (10)0.0300 (8)0.0000.0017 (7)0.000
C50.0383 (11)0.0433 (12)0.0276 (9)0.0000.0025 (8)0.000
C60.0359 (11)0.0453 (13)0.0425 (12)0.0000.0054 (9)0.000
C70.0378 (12)0.0545 (15)0.0606 (15)0.0000.0079 (11)0.000
N80.0523 (13)0.0584 (13)0.0492 (13)0.0000.0175 (10)0.000
C8A0.0551 (14)0.0411 (12)0.0318 (10)0.0000.0080 (10)0.000
C90.0517 (15)0.079 (2)0.0323 (12)0.0000.0062 (10)0.000
C100.0435 (13)0.0637 (17)0.0515 (14)0.0000.0112 (11)0.000
N100.0667 (16)0.105 (2)0.0615 (16)0.0000.0272 (13)0.000
Geometric parameters (Å, º) top
N1—C8A1.321 (3)C6—C71.414 (3)
N1—C21.350 (4)C6—C101.437 (3)
C2—N31.323 (3)C7—N81.306 (3)
C2—H20.93C7—H70.93
N3—N41.368 (3)N8—C8A1.354 (3)
N4—C51.360 (3)C9—H9A0.95 (3)
N4—C8A1.390 (3)C9—H9B0.99 (3)
C5—C61.372 (3)C10—N101.136 (3)
C5—C91.482 (3)
C8A—N1—C2102.7 (2)C7—C6—C10118.5 (2)
N3—C2—N1117.5 (2)N8—C7—C6124.9 (2)
N3—C2—H2121.2N8—C7—H7117.6
N1—C2—H2121.2C6—C7—H7117.6
C2—N3—N4100.9 (2)C7—N8—C8A115.5 (2)
C5—N4—N3126.10 (18)N1—C8A—N8129.6 (2)
C5—N4—C8A124.25 (19)N1—C8A—N4109.2 (2)
N3—N4—C8A109.65 (18)N8—C8A—N4121.2 (2)
N4—C5—C6113.77 (19)C5—C9—H9A111.0 (18)
N4—C5—C9118.4 (2)C5—C9—H9B109.7 (16)
C6—C5—C9127.8 (2)H9A—C9—H9B109.2 (18)
C5—C6—C7120.4 (2)N10—C10—C6176.4 (3)
C5—C6—C10121.1 (2)
C8A—N1—C2—N30.0C5—C6—C7—N80.0
N1—C2—N3—N40.0C10—C6—C7—N8180.0
C2—N3—N4—C5180.0C6—C7—N8—C8A0.0
C2—N3—N4—C8A0.0C2—N1—C8A—N8180.0
N3—N4—C5—C6180.0C2—N1—C8A—N40.0
C8A—N4—C5—C60.0C7—N8—C8A—N1180.0
N3—N4—C5—C90.0C7—N8—C8A—N40.0
C8A—N4—C5—C9180.0C5—N4—C8A—N1180.0
N4—C5—C6—C70.0N3—N4—C8A—N10.0
C9—C5—C6—C7180.0C5—N4—C8A—N80.0
N4—C5—C6—C10180.0N3—N4—C8A—N8180.0
C9—C5—C6—C100.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N10i0.932.473.366 (4)161
C7—H7···N3ii0.932.423.265 (4)151
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z.
 

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