organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N-(4,6-Di­methyl­pyrimidin-2-yl)-1H-benzimidazol-2-amine

aChemistry & Environmental Science Division, School of Science, Manchester Metropolitan University, England, bDepartment of Chemistry, Sohag University, Sohag, Egypt, cDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 20 February 2011; accepted 21 February 2011; online 26 February 2011)

There are two independent mol­ecules in the asymmetric unit of the title compound, C13H13N5. In each mol­ecule, an amino N atom is connected to a benzimidazole fused-ring system and a pyrimidine ring [these are aligned at 1.3 (1)° in one independent mol­ecule and at 5.4 (1)° in the other]. The amino N atom of the fused ring forms an intra­molecular N—H⋯O hydrogen bond to a pyrimidine N atom in each mol­ecule. The amino N atom connecting the two ring systems inter­acts with the other N atom of the pyrimidine ring of an adjacent mol­ecule, generating centrosymmetric hydrogen-bonded dimers.

Related literature

For the synthesis, see: Bossio et al. (1985[Bossio, R., Marcaccini, S., Parrini, V. & Pepino, R. (1985). J. Heterocycl. Chem. 22, 1147-1148.]); Shestakov et al. (2006[Shestakov, A. S., Gusakova, N. V., Shikhaliev, Kh. S. & Zagoruiko, A. V. (2006). Russ. J. Gen. Chem. 76, 1719-1724.]).

[Scheme 1]

Experimental

Crystal data
  • C13H13N5

  • Mr = 239.28

  • Triclinic, [P \overline 1]

  • a = 8.2836 (4) Å

  • b = 9.6135 (5) Å

  • c = 16.5694 (8) Å

  • α = 92.121 (1)°

  • β = 96.100 (1)°

  • γ = 112.597 (1)°

  • V = 1206.94 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 295 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII diffractometer

  • 13373 measured reflections

  • 5550 independent reflections

  • 4124 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.136

  • S = 1.01

  • 5550 reflections

  • 345 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯N5 0.86 (1) 2.05 (2) 2.664 (2) 128 (2)
N3—H3⋯N2i 0.87 (1) 2.05 (1) 2.912 (2) 170 (2)
N7—H7⋯N10 0.87 (1) 2.10 (2) 2.695 (2) 125 (2)
N8—H8⋯N6ii 0.87 (1) 2.05 (1) 2.908 (2) 170 (2)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+2, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The reported synthesis involves the reaction of 4,6-dimethylpyrimidin-2-ylcyanamide with o-phenylenediamine, and it illustrates the type of heterocycles that are formed by the reaction of cyanamides with N,N-binucleophiles (Shestakov et al., 2006). The unsubstituted compound was reported earlier (Bossio et al., 1985). The present synthesis is a more convenient synthesis that uses acetylacetone as one of the reactants. An amino N atom in the approximately planar C13H13N5 molecule is connected to a benzimidazoyl fused-ring and a pyrimidyl ring; the amino N atom of the fused ring forms an intramolecular N–H···O hydrogen bond to a pyridmidyl N atom (Scheme I, Fig. 1). There are two independent molecules; each molecule is connected to an inversion-related molecule by an N–H···O hydrogen bond.

Related literature top

For the synthesis, see: Bossio et al. (1985); Shestakov et al. (2006).

Experimental top

1H-Benzo[d]imidazol-2-yliminomethanediamine (0.05 mol) and acetylacetone (0.10 mol, approx.10 ml) along with several drops of acetic acid were heated at 473 for 1 h. The solid that formed on cooling was collected and recrystallized from ethanol to give the title compound in 80% yield; m.p. 623 K.

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C–H 0.93 to 0.96 Å; U(H) 1.2 to 1.5U(C)] and were included in the refinement in the riding model approximation.

The amino H-atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H 0.86±0.01 Å; their temperature factors were refined.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C13H13N5 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
N-(4,6-Dimethylpyrimidin-2-yl)-1H-benzimidazol-2-amine top
Crystal data top
C13H13N5Z = 4
Mr = 239.28F(000) = 504
Triclinic, P1Dx = 1.317 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2836 (4) ÅCell parameters from 4428 reflections
b = 9.6135 (5) Åθ = 2.3–27.4°
c = 16.5694 (8) ŵ = 0.09 mm1
α = 92.121 (1)°T = 295 K
β = 96.100 (1)°Prism, colorless
γ = 112.597 (1)°0.30 × 0.20 × 0.20 mm
V = 1206.94 (10) Å3
Data collection top
Bruker APEXII
diffractometer
4124 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 27.5°, θmin = 1.2°
ϕ and ω scansh = 1010
13373 measured reflectionsk = 1212
5550 independent reflectionsl = 2121
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0736P)2 + 0.1933P]
where P = (Fo2 + 2Fc2)/3
5550 reflections(Δ/σ)max = 0.001
345 parametersΔρmax = 0.25 e Å3
4 restraintsΔρmin = 0.18 e Å3
Crystal data top
C13H13N5γ = 112.597 (1)°
Mr = 239.28V = 1206.94 (10) Å3
Triclinic, P1Z = 4
a = 8.2836 (4) ÅMo Kα radiation
b = 9.6135 (5) ŵ = 0.09 mm1
c = 16.5694 (8) ÅT = 295 K
α = 92.121 (1)°0.30 × 0.20 × 0.20 mm
β = 96.100 (1)°
Data collection top
Bruker APEXII
diffractometer
4124 reflections with I > 2σ(I)
13373 measured reflectionsRint = 0.019
5550 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0444 restraints
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.25 e Å3
5550 reflectionsΔρmin = 0.18 e Å3
345 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.66435 (17)0.61916 (15)0.45010 (8)0.0480 (3)
N20.80016 (16)0.45944 (14)0.43969 (8)0.0470 (3)
N30.94151 (17)0.67635 (15)0.53228 (8)0.0498 (3)
N41.11489 (17)0.88346 (14)0.61816 (8)0.0491 (3)
N50.83527 (16)0.86534 (14)0.55242 (8)0.0477 (3)
N60.98905 (15)1.11808 (14)0.92502 (8)0.0453 (3)
N70.72463 (16)1.09201 (14)0.86230 (8)0.0452 (3)
N80.74067 (16)0.92463 (15)0.96388 (8)0.0485 (3)
N90.52809 (16)0.73369 (14)1.01630 (8)0.0477 (3)
N100.44770 (16)0.87329 (14)0.91397 (8)0.0464 (3)
C10.5574 (2)0.50529 (17)0.39234 (9)0.0453 (3)
C20.3985 (2)0.48064 (19)0.34608 (11)0.0570 (4)
H20.34150.54640.35160.068*
C30.3283 (2)0.3542 (2)0.29138 (11)0.0648 (5)
H3A0.22190.33430.25900.078*
C40.4132 (2)0.2562 (2)0.28378 (11)0.0646 (5)
H40.36300.17260.24580.077*
C50.5706 (2)0.27942 (19)0.33104 (10)0.0566 (4)
H50.62580.21220.32610.068*
C60.64326 (19)0.40638 (17)0.38613 (9)0.0446 (3)
C70.80551 (19)0.58625 (16)0.47531 (9)0.0433 (3)
C80.96246 (19)0.81387 (17)0.56914 (9)0.0444 (3)
C91.1398 (2)1.01836 (18)0.65380 (10)0.0502 (4)
C101.0141 (2)1.07950 (19)0.64206 (10)0.0541 (4)
H101.03171.17230.66840.065*
C110.8619 (2)0.99939 (18)0.59025 (10)0.0492 (4)
C121.3142 (2)1.1021 (2)0.70528 (13)0.0679 (5)
H12A1.39691.05980.69210.102*
H12B1.29941.09300.76180.102*
H12C1.35771.20690.69490.102*
C130.7188 (2)1.0572 (2)0.57189 (12)0.0638 (5)
H13A0.68951.05280.51400.096*
H13B0.75911.16000.59460.096*
H13C0.61630.99590.59530.096*
C141.01079 (19)1.22562 (16)0.86868 (9)0.0423 (3)
C151.1636 (2)1.33597 (18)0.84877 (10)0.0510 (4)
H151.27381.34680.87430.061*
C161.1476 (2)1.42941 (19)0.78990 (10)0.0563 (4)
H161.24881.50410.77580.068*
C170.9839 (2)1.41438 (19)0.75126 (10)0.0569 (4)
H170.97771.47890.71170.068*
C180.8299 (2)1.30521 (19)0.77048 (10)0.0525 (4)
H180.71991.29540.74510.063*
C190.84684 (19)1.21133 (16)0.82922 (9)0.0433 (3)
C200.81693 (18)1.04241 (16)0.91841 (9)0.0417 (3)
C210.56341 (18)0.84116 (16)0.96416 (9)0.0433 (3)
C220.3584 (2)0.64850 (18)1.01769 (10)0.0489 (4)
C230.2285 (2)0.67368 (19)0.96860 (11)0.0554 (4)
H230.11010.61470.97050.066*
C240.27647 (19)0.78683 (18)0.91699 (10)0.0494 (4)
C250.3156 (2)0.5228 (2)1.07291 (12)0.0647 (5)
H25A0.40530.55041.11910.097*
H25B0.31050.43261.04390.097*
H25C0.20360.50481.09110.097*
C260.1440 (2)0.8194 (2)0.86077 (12)0.0683 (5)
H26A0.16960.92570.86600.102*
H26B0.02800.76430.87460.102*
H26C0.14950.78890.80560.102*
H10.653 (2)0.6974 (15)0.4721 (10)0.062 (5)*
H31.0279 (19)0.647 (2)0.5423 (11)0.067 (5)*
H70.6096 (12)1.0539 (19)0.8546 (11)0.063 (5)*
H80.811 (2)0.902 (2)0.9979 (9)0.059 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0468 (7)0.0444 (7)0.0547 (8)0.0227 (6)0.0035 (6)0.0018 (6)
N20.0440 (7)0.0451 (7)0.0521 (7)0.0199 (6)0.0010 (6)0.0007 (6)
N30.0447 (7)0.0479 (7)0.0585 (8)0.0243 (6)0.0064 (6)0.0042 (6)
N40.0465 (7)0.0477 (7)0.0525 (7)0.0203 (6)0.0013 (6)0.0007 (6)
N50.0470 (7)0.0495 (7)0.0504 (7)0.0239 (6)0.0032 (6)0.0015 (6)
N60.0374 (6)0.0460 (7)0.0527 (7)0.0178 (5)0.0004 (5)0.0092 (5)
N70.0379 (6)0.0476 (7)0.0497 (7)0.0186 (6)0.0035 (5)0.0055 (5)
N80.0357 (6)0.0484 (7)0.0606 (8)0.0167 (5)0.0021 (6)0.0146 (6)
N90.0400 (6)0.0491 (7)0.0567 (8)0.0203 (6)0.0054 (6)0.0072 (6)
N100.0383 (6)0.0493 (7)0.0498 (7)0.0179 (5)0.0032 (5)0.0003 (6)
C10.0457 (8)0.0438 (8)0.0443 (8)0.0157 (6)0.0015 (6)0.0101 (6)
C20.0526 (9)0.0554 (9)0.0616 (10)0.0228 (8)0.0072 (8)0.0119 (8)
C30.0567 (10)0.0670 (11)0.0595 (10)0.0173 (9)0.0133 (8)0.0074 (9)
C40.0641 (11)0.0588 (10)0.0566 (10)0.0128 (9)0.0057 (8)0.0046 (8)
C50.0571 (10)0.0504 (9)0.0582 (10)0.0182 (8)0.0030 (8)0.0021 (7)
C60.0438 (8)0.0451 (8)0.0438 (8)0.0160 (6)0.0047 (6)0.0079 (6)
C70.0415 (7)0.0440 (8)0.0456 (8)0.0189 (6)0.0020 (6)0.0058 (6)
C80.0442 (8)0.0441 (8)0.0458 (8)0.0187 (6)0.0041 (6)0.0032 (6)
C90.0507 (9)0.0489 (8)0.0486 (8)0.0178 (7)0.0029 (7)0.0017 (7)
C100.0586 (10)0.0495 (9)0.0560 (9)0.0245 (8)0.0055 (8)0.0047 (7)
C110.0523 (9)0.0510 (8)0.0501 (8)0.0259 (7)0.0095 (7)0.0035 (7)
C120.0601 (11)0.0584 (10)0.0767 (12)0.0205 (9)0.0115 (9)0.0104 (9)
C130.0617 (11)0.0672 (11)0.0729 (12)0.0382 (9)0.0051 (9)0.0016 (9)
C140.0429 (7)0.0425 (7)0.0427 (7)0.0196 (6)0.0004 (6)0.0015 (6)
C150.0464 (8)0.0503 (9)0.0527 (9)0.0161 (7)0.0018 (7)0.0046 (7)
C160.0619 (10)0.0485 (9)0.0538 (9)0.0158 (8)0.0094 (8)0.0069 (7)
C170.0740 (11)0.0530 (9)0.0490 (9)0.0308 (9)0.0052 (8)0.0115 (7)
C180.0580 (9)0.0567 (9)0.0482 (9)0.0306 (8)0.0026 (7)0.0052 (7)
C190.0472 (8)0.0428 (8)0.0418 (7)0.0218 (6)0.0007 (6)0.0004 (6)
C200.0381 (7)0.0419 (7)0.0466 (8)0.0193 (6)0.0016 (6)0.0028 (6)
C210.0370 (7)0.0434 (8)0.0503 (8)0.0181 (6)0.0009 (6)0.0005 (6)
C220.0431 (8)0.0494 (8)0.0560 (9)0.0194 (7)0.0101 (7)0.0004 (7)
C230.0370 (8)0.0599 (10)0.0646 (10)0.0145 (7)0.0051 (7)0.0024 (8)
C240.0372 (7)0.0552 (9)0.0527 (9)0.0176 (7)0.0023 (6)0.0058 (7)
C250.0547 (10)0.0660 (11)0.0781 (12)0.0242 (9)0.0201 (9)0.0210 (9)
C260.0422 (9)0.0854 (13)0.0718 (12)0.0228 (9)0.0082 (8)0.0089 (10)
Geometric parameters (Å, º) top
N1—C71.3535 (18)C5—H50.9300
N1—C11.377 (2)C9—C101.380 (2)
N1—H10.86 (1)C9—C121.502 (2)
N2—C71.3176 (19)C10—C111.376 (2)
N2—C61.3960 (19)C10—H100.9300
N3—C71.3689 (19)C11—C131.499 (2)
N3—C81.3756 (19)C12—H12A0.9600
N3—H30.87 (1)C12—H12B0.9600
N4—C91.336 (2)C12—H12C0.9600
N4—C81.3396 (19)C13—H13A0.9600
N5—C81.3343 (18)C13—H13B0.9600
N5—C111.340 (2)C13—H13C0.9600
N6—C201.3183 (18)C14—C151.385 (2)
N6—C141.3917 (19)C14—C191.397 (2)
N7—C201.3558 (18)C15—C161.380 (2)
N7—C191.383 (2)C15—H150.9300
N7—H70.87 (1)C16—C171.388 (2)
N8—C201.3650 (19)C16—H160.9300
N8—C211.3771 (19)C17—C181.383 (2)
N8—H80.87 (1)C17—H170.9300
N9—C221.3310 (19)C18—C191.384 (2)
N9—C211.3367 (19)C18—H180.9300
N10—C211.3352 (18)C22—C231.380 (2)
N10—C241.3481 (19)C22—C251.498 (2)
C1—C21.382 (2)C23—C241.372 (2)
C1—C61.396 (2)C23—H230.9300
C2—C31.378 (3)C24—C261.496 (2)
C2—H20.9300C25—H25A0.9600
C3—C41.384 (3)C25—H25B0.9600
C3—H3A0.9300C25—H25C0.9600
C4—C51.382 (2)C26—H26A0.9600
C4—H40.9300C26—H26B0.9600
C5—C61.386 (2)C26—H26C0.9600
C7—N1—C1106.87 (13)C9—C12—H12C109.5
C7—N1—H1120.2 (12)H12A—C12—H12C109.5
C1—N1—H1132.8 (12)H12B—C12—H12C109.5
C7—N2—C6104.12 (12)C11—C13—H13A109.5
C7—N3—C8126.91 (13)C11—C13—H13B109.5
C7—N3—H3115.8 (13)H13A—C13—H13B109.5
C8—N3—H3117.0 (13)C11—C13—H13C109.5
C9—N4—C8115.66 (13)H13A—C13—H13C109.5
C8—N5—C11116.23 (13)H13B—C13—H13C109.5
C20—N6—C14104.20 (12)C15—C14—N6129.94 (13)
C20—N7—C19106.69 (12)C15—C14—C19119.88 (14)
C20—N7—H7121.9 (12)N6—C14—C19110.18 (13)
C19—N7—H7131.3 (12)C16—C15—C14118.09 (15)
C20—N8—C21127.59 (13)C16—C15—H15121.0
C20—N8—H8116.5 (13)C14—C15—H15121.0
C21—N8—H8115.9 (12)C15—C16—C17121.51 (16)
C22—N9—C21116.15 (13)C15—C16—H16119.2
C21—N10—C24115.57 (14)C17—C16—H16119.2
N1—C1—C2132.25 (15)C18—C17—C16121.25 (15)
N1—C1—C6105.39 (13)C18—C17—H17119.4
C2—C1—C6122.37 (15)C16—C17—H17119.4
C3—C2—C1116.96 (16)C17—C18—C19116.95 (15)
C3—C2—H2121.5C17—C18—H18121.5
C1—C2—H2121.5C19—C18—H18121.5
C2—C3—C4121.27 (16)N7—C19—C18132.51 (14)
C2—C3—H3A119.4N7—C19—C14105.17 (12)
C4—C3—H3A119.4C18—C19—C14122.32 (15)
C5—C4—C3121.77 (16)N6—C20—N7113.75 (13)
C5—C4—H4119.1N6—C20—N8122.52 (13)
C3—C4—H4119.1N7—C20—N8123.73 (13)
C4—C5—C6117.67 (16)N10—C21—N9127.34 (13)
C4—C5—H5121.2N10—C21—N8118.60 (14)
C6—C5—H5121.2N9—C21—N8114.06 (12)
C5—C6—C1119.94 (14)N9—C22—C23120.91 (15)
C5—C6—N2130.14 (14)N9—C22—C25117.17 (14)
C1—C6—N2109.91 (13)C23—C22—C25121.90 (15)
N2—C7—N1113.70 (13)C24—C23—C22119.11 (14)
N2—C7—N3123.06 (13)C24—C23—H23120.4
N1—C7—N3123.24 (14)C22—C23—H23120.4
N5—C8—N4126.91 (14)N10—C24—C23120.91 (14)
N5—C8—N3118.65 (13)N10—C24—C26116.69 (15)
N4—C8—N3114.42 (13)C23—C24—C26122.39 (15)
N4—C9—C10121.78 (15)C22—C25—H25A109.5
N4—C9—C12116.46 (14)C22—C25—H25B109.5
C10—C9—C12121.74 (15)H25A—C25—H25B109.5
C11—C10—C9118.16 (15)C22—C25—H25C109.5
C11—C10—H10120.9H25A—C25—H25C109.5
C9—C10—H10120.9H25B—C25—H25C109.5
N5—C11—C10121.22 (14)C24—C26—H26A109.5
N5—C11—C13116.37 (15)C24—C26—H26B109.5
C10—C11—C13122.40 (15)H26A—C26—H26B109.5
C9—C12—H12A109.5C24—C26—H26C109.5
C9—C12—H12B109.5H26A—C26—H26C109.5
H12A—C12—H12B109.5H26B—C26—H26C109.5
C7—N1—C1—C2179.49 (17)C20—N6—C14—C15179.64 (15)
C7—N1—C1—C60.26 (16)C20—N6—C14—C190.28 (16)
N1—C1—C2—C3178.38 (17)N6—C14—C15—C16179.89 (15)
C6—C1—C2—C31.3 (2)C19—C14—C15—C160.2 (2)
C1—C2—C3—C40.4 (3)C14—C15—C16—C170.0 (2)
C2—C3—C4—C50.7 (3)C15—C16—C17—C180.2 (3)
C3—C4—C5—C60.9 (3)C16—C17—C18—C190.6 (2)
C4—C5—C6—C10.0 (2)C20—N7—C19—C18179.50 (16)
C4—C5—C6—N2178.51 (16)C20—N7—C19—C140.38 (16)
N1—C1—C6—C5178.65 (14)C17—C18—C19—N7179.37 (15)
C2—C1—C6—C51.1 (2)C17—C18—C19—C140.8 (2)
N1—C1—C6—N20.17 (17)C15—C14—C19—N7179.52 (13)
C2—C1—C6—N2179.95 (14)N6—C14—C19—N70.42 (16)
C7—N2—C6—C5178.13 (16)C15—C14—C19—C180.6 (2)
C7—N2—C6—C10.53 (16)N6—C14—C19—C18179.48 (14)
C6—N2—C7—N10.72 (17)C14—N6—C20—N70.03 (17)
C6—N2—C7—N3179.09 (14)C14—N6—C20—N8179.56 (13)
C1—N1—C7—N20.64 (18)C19—N7—C20—N60.23 (17)
C1—N1—C7—N3179.17 (14)C19—N7—C20—N8179.82 (14)
C8—N3—C7—N2176.24 (14)C21—N8—C20—N6177.63 (14)
C8—N3—C7—N13.6 (3)C21—N8—C20—N72.8 (3)
C11—N5—C8—N41.6 (2)C24—N10—C21—N90.1 (2)
C11—N5—C8—N3179.66 (14)C24—N10—C21—N8179.65 (13)
C9—N4—C8—N50.2 (2)C22—N9—C21—N100.6 (2)
C9—N4—C8—N3179.02 (13)C22—N9—C21—N8178.95 (13)
C7—N3—C8—N53.8 (2)C20—N8—C21—N101.4 (2)
C7—N3—C8—N4175.12 (15)C20—N8—C21—N9179.03 (14)
C8—N4—C9—C101.5 (2)C21—N9—C22—C231.1 (2)
C8—N4—C9—C12176.69 (15)C21—N9—C22—C25177.35 (14)
N4—C9—C10—C111.8 (3)N9—C22—C23—C241.0 (2)
C12—C9—C10—C11176.30 (16)C25—C22—C23—C24177.42 (16)
C8—N5—C11—C101.2 (2)C21—N10—C24—C230.3 (2)
C8—N5—C11—C13179.73 (14)C21—N10—C24—C26179.39 (14)
C9—C10—C11—N50.4 (3)C22—C23—C24—N100.2 (2)
C9—C10—C11—C13178.64 (16)C22—C23—C24—C26178.81 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N50.86 (1)2.05 (2)2.664 (2)128 (2)
N3—H3···N2i0.87 (1)2.05 (1)2.912 (2)170 (2)
N7—H7···N100.87 (1)2.10 (2)2.695 (2)125 (2)
N8—H8···N6ii0.87 (1)2.05 (1)2.908 (2)170 (2)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y+2, z+2.

Experimental details

Crystal data
Chemical formulaC13H13N5
Mr239.28
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)8.2836 (4), 9.6135 (5), 16.5694 (8)
α, β, γ (°)92.121 (1), 96.100 (1), 112.597 (1)
V3)1206.94 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13373, 5550, 4124
Rint0.019
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.136, 1.01
No. of reflections5550
No. of parameters345
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.18

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N50.86 (1)2.05 (2)2.664 (2)128 (2)
N3—H3···N2i0.87 (1)2.05 (1)2.912 (2)170 (2)
N7—H7···N100.87 (1)2.10 (2)2.695 (2)125 (2)
N8—H8···N6ii0.87 (1)2.05 (1)2.908 (2)170 (2)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y+2, z+2.
 

Acknowledgements

We thank Manchester Metropolitan University, Baku State University and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBossio, R., Marcaccini, S., Parrini, V. & Pepino, R. (1985). J. Heterocycl. Chem. 22, 1147–1148.  CrossRef CAS
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShestakov, A. S., Gusakova, N. V., Shikhaliev, Kh. S. & Zagoruiko, A. V. (2006). Russ. J. Gen. Chem. 76, 1719–1724.  Web of Science CrossRef
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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