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

Mohamed, S.K.; El-Remaily, M.A.A.; Gurbanov, A.V.; Khalilov, A.N.; Ng, S.W.

doi:10.1107/S1600536811006507

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o719

doi:10.1107/S1600536811006507

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

Shaaban Kamel Mohamed,^a Mahmoud A. A. El-Remaily,^b Atash V. Gurbanov,^c Ali N. Khalilov ^c and Seik Weng Ng ^d ^*

^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 ); Shestakov et al. (2006 ).

Experimental

Crystal data

C₁₃H₁₃N₅
M_r = 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)
R_int = 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
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006507/hg5003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006507/hg5003Isup2.hkl

checkCIF report

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.

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

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

C₁₃H₁₃N₅	Z = 4
M_r = 239.28	F(000) = 504
Triclinic, P1	D_x = 1.317 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2836 (4) Å	Cell parameters from 4428 reflections
b = 9.6135 (5) Å	θ = 2.3–27.4°
c = 16.5694 (8) Å	µ = 0.09 mm⁻¹
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 tube	R_int = 0.019
Graphite monochromator	θ_max = 27.5°, θ_min = 1.2°
ϕ and ω scans	h = −10→10
13373 measured reflections	k = −12→12
5550 independent reflections	l = −21→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0736P)² + 0.1933P] where P = (F_o² + 2F_c²)/3
5550 reflections	(Δ/σ)_max = 0.001
345 parameters	Δρ_max = 0.25 e Å⁻³
4 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₃H₁₃N₅	γ = 112.597 (1)°
M_r = 239.28	V = 1206.94 (10) Å³
Triclinic, P1	Z = 4
a = 8.2836 (4) Å	Mo Kα radiation
b = 9.6135 (5) Å	µ = 0.09 mm⁻¹
c = 16.5694 (8) Å	T = 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 reflections	R_int = 0.019
5550 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	4 restraints
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.25 e Å⁻³
5550 reflections	Δρ_min = −0.18 e Å⁻³
345 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.66435 (17)	0.61916 (15)	0.45010 (8)	0.0480 (3)
N2	0.80016 (16)	0.45944 (14)	0.43969 (8)	0.0470 (3)
N3	0.94151 (17)	0.67635 (15)	0.53228 (8)	0.0498 (3)
N4	1.11489 (17)	0.88346 (14)	0.61816 (8)	0.0491 (3)
N5	0.83527 (16)	0.86534 (14)	0.55242 (8)	0.0477 (3)
N6	0.98905 (15)	1.11808 (14)	0.92502 (8)	0.0453 (3)
N7	0.72463 (16)	1.09201 (14)	0.86230 (8)	0.0452 (3)
N8	0.74067 (16)	0.92463 (15)	0.96388 (8)	0.0485 (3)
N9	0.52809 (16)	0.73369 (14)	1.01630 (8)	0.0477 (3)
N10	0.44770 (16)	0.87329 (14)	0.91397 (8)	0.0464 (3)
C1	0.5574 (2)	0.50529 (17)	0.39234 (9)	0.0453 (3)
C2	0.3985 (2)	0.48064 (19)	0.34608 (11)	0.0570 (4)
H2	0.3415	0.5464	0.3516	0.068*
C3	0.3283 (2)	0.3542 (2)	0.29138 (11)	0.0648 (5)
H3A	0.2219	0.3343	0.2590	0.078*
C4	0.4132 (2)	0.2562 (2)	0.28378 (11)	0.0646 (5)
H4	0.3630	0.1726	0.2458	0.077*
C5	0.5706 (2)	0.27942 (19)	0.33104 (10)	0.0566 (4)
H5	0.6258	0.2122	0.3261	0.068*
C6	0.64326 (19)	0.40638 (17)	0.38613 (9)	0.0446 (3)
C7	0.80551 (19)	0.58625 (16)	0.47531 (9)	0.0433 (3)
C8	0.96246 (19)	0.81387 (17)	0.56914 (9)	0.0444 (3)
C9	1.1398 (2)	1.01836 (18)	0.65380 (10)	0.0502 (4)
C10	1.0141 (2)	1.07950 (19)	0.64206 (10)	0.0541 (4)
H10	1.0317	1.1723	0.6684	0.065*
C11	0.8619 (2)	0.99939 (18)	0.59025 (10)	0.0492 (4)
C12	1.3142 (2)	1.1021 (2)	0.70528 (13)	0.0679 (5)
H12A	1.3969	1.0598	0.6921	0.102*
H12B	1.2994	1.0930	0.7618	0.102*
H12C	1.3577	1.2069	0.6949	0.102*
C13	0.7188 (2)	1.0572 (2)	0.57189 (12)	0.0638 (5)
H13A	0.6895	1.0528	0.5140	0.096*
H13B	0.7591	1.1600	0.5946	0.096*
H13C	0.6163	0.9959	0.5953	0.096*
C14	1.01079 (19)	1.22562 (16)	0.86868 (9)	0.0423 (3)
C15	1.1636 (2)	1.33597 (18)	0.84877 (10)	0.0510 (4)
H15	1.2738	1.3468	0.8743	0.061*
C16	1.1476 (2)	1.42941 (19)	0.78990 (10)	0.0563 (4)
H16	1.2488	1.5041	0.7758	0.068*
C17	0.9839 (2)	1.41438 (19)	0.75126 (10)	0.0569 (4)
H17	0.9777	1.4789	0.7117	0.068*
C18	0.8299 (2)	1.30521 (19)	0.77048 (10)	0.0525 (4)
H18	0.7199	1.2954	0.7451	0.063*
C19	0.84684 (19)	1.21133 (16)	0.82922 (9)	0.0433 (3)
C20	0.81693 (18)	1.04241 (16)	0.91841 (9)	0.0417 (3)
C21	0.56341 (18)	0.84116 (16)	0.96416 (9)	0.0433 (3)
C22	0.3584 (2)	0.64850 (18)	1.01769 (10)	0.0489 (4)
C23	0.2285 (2)	0.67368 (19)	0.96860 (11)	0.0554 (4)
H23	0.1101	0.6147	0.9705	0.066*
C24	0.27647 (19)	0.78683 (18)	0.91699 (10)	0.0494 (4)
C25	0.3156 (2)	0.5228 (2)	1.07291 (12)	0.0647 (5)
H25A	0.4053	0.5504	1.1191	0.097*
H25B	0.3105	0.4326	1.0439	0.097*
H25C	0.2036	0.5048	1.0911	0.097*
C26	0.1440 (2)	0.8194 (2)	0.86077 (12)	0.0683 (5)
H26A	0.1696	0.9257	0.8660	0.102*
H26B	0.0280	0.7643	0.8746	0.102*
H26C	0.1495	0.7889	0.8056	0.102*
H1	0.653 (2)	0.6974 (15)	0.4721 (10)	0.062 (5)*
H3	1.0279 (19)	0.647 (2)	0.5423 (11)	0.067 (5)*
H7	0.6096 (12)	1.0539 (19)	0.8546 (11)	0.063 (5)*
H8	0.811 (2)	0.902 (2)	0.9979 (9)	0.059 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0468 (7)	0.0444 (7)	0.0547 (8)	0.0227 (6)	−0.0035 (6)	0.0018 (6)
N2	0.0440 (7)	0.0451 (7)	0.0521 (7)	0.0199 (6)	−0.0010 (6)	−0.0007 (6)
N3	0.0447 (7)	0.0479 (7)	0.0585 (8)	0.0243 (6)	−0.0064 (6)	−0.0042 (6)
N4	0.0465 (7)	0.0477 (7)	0.0525 (7)	0.0203 (6)	−0.0013 (6)	−0.0007 (6)
N5	0.0470 (7)	0.0495 (7)	0.0504 (7)	0.0239 (6)	0.0032 (6)	0.0015 (6)
N6	0.0374 (6)	0.0460 (7)	0.0527 (7)	0.0178 (5)	−0.0004 (5)	0.0092 (5)
N7	0.0379 (6)	0.0476 (7)	0.0497 (7)	0.0186 (6)	−0.0035 (5)	0.0055 (5)
N8	0.0357 (6)	0.0484 (7)	0.0606 (8)	0.0167 (5)	−0.0021 (6)	0.0146 (6)
N9	0.0400 (6)	0.0491 (7)	0.0567 (8)	0.0203 (6)	0.0054 (6)	0.0072 (6)
N10	0.0383 (6)	0.0493 (7)	0.0498 (7)	0.0179 (5)	−0.0032 (5)	−0.0003 (6)
C1	0.0457 (8)	0.0438 (8)	0.0443 (8)	0.0157 (6)	0.0015 (6)	0.0101 (6)
C2	0.0526 (9)	0.0554 (9)	0.0616 (10)	0.0228 (8)	−0.0072 (8)	0.0119 (8)
C3	0.0567 (10)	0.0670 (11)	0.0595 (10)	0.0173 (9)	−0.0133 (8)	0.0074 (9)
C4	0.0641 (11)	0.0588 (10)	0.0566 (10)	0.0128 (9)	−0.0057 (8)	−0.0046 (8)
C5	0.0571 (10)	0.0504 (9)	0.0582 (10)	0.0182 (8)	0.0030 (8)	−0.0021 (7)
C6	0.0438 (8)	0.0451 (8)	0.0438 (8)	0.0160 (6)	0.0047 (6)	0.0079 (6)
C7	0.0415 (7)	0.0440 (8)	0.0456 (8)	0.0189 (6)	0.0020 (6)	0.0058 (6)
C8	0.0442 (8)	0.0441 (8)	0.0458 (8)	0.0187 (6)	0.0041 (6)	0.0032 (6)
C9	0.0507 (9)	0.0489 (8)	0.0486 (8)	0.0178 (7)	0.0029 (7)	0.0017 (7)
C10	0.0586 (10)	0.0495 (9)	0.0560 (9)	0.0245 (8)	0.0055 (8)	−0.0047 (7)
C11	0.0523 (9)	0.0510 (8)	0.0501 (8)	0.0259 (7)	0.0095 (7)	0.0035 (7)
C12	0.0601 (11)	0.0584 (10)	0.0767 (12)	0.0205 (9)	−0.0115 (9)	−0.0104 (9)
C13	0.0617 (11)	0.0672 (11)	0.0729 (12)	0.0382 (9)	0.0051 (9)	−0.0016 (9)
C14	0.0429 (7)	0.0425 (7)	0.0427 (7)	0.0196 (6)	0.0004 (6)	0.0015 (6)
C15	0.0464 (8)	0.0503 (9)	0.0527 (9)	0.0161 (7)	0.0018 (7)	0.0046 (7)
C16	0.0619 (10)	0.0485 (9)	0.0538 (9)	0.0158 (8)	0.0094 (8)	0.0069 (7)
C17	0.0740 (11)	0.0530 (9)	0.0490 (9)	0.0308 (9)	0.0052 (8)	0.0115 (7)
C18	0.0580 (9)	0.0567 (9)	0.0482 (9)	0.0306 (8)	−0.0026 (7)	0.0052 (7)
C19	0.0472 (8)	0.0428 (8)	0.0418 (7)	0.0218 (6)	−0.0007 (6)	−0.0004 (6)
C20	0.0381 (7)	0.0419 (7)	0.0466 (8)	0.0193 (6)	−0.0016 (6)	0.0028 (6)
C21	0.0370 (7)	0.0434 (8)	0.0503 (8)	0.0181 (6)	0.0009 (6)	−0.0005 (6)
C22	0.0431 (8)	0.0494 (8)	0.0560 (9)	0.0194 (7)	0.0101 (7)	0.0004 (7)
C23	0.0370 (8)	0.0599 (10)	0.0646 (10)	0.0145 (7)	0.0051 (7)	0.0024 (8)
C24	0.0372 (7)	0.0552 (9)	0.0527 (9)	0.0176 (7)	−0.0023 (6)	−0.0058 (7)
C25	0.0547 (10)	0.0660 (11)	0.0781 (12)	0.0242 (9)	0.0201 (9)	0.0210 (9)
C26	0.0422 (9)	0.0854 (13)	0.0718 (12)	0.0228 (9)	−0.0082 (8)	0.0089 (10)

Geometric parameters (Å, º) top

N1—C7	1.3535 (18)	C5—H5	0.9300
N1—C1	1.377 (2)	C9—C10	1.380 (2)
N1—H1	0.86 (1)	C9—C12	1.502 (2)
N2—C7	1.3176 (19)	C10—C11	1.376 (2)
N2—C6	1.3960 (19)	C10—H10	0.9300
N3—C7	1.3689 (19)	C11—C13	1.499 (2)
N3—C8	1.3756 (19)	C12—H12A	0.9600
N3—H3	0.87 (1)	C12—H12B	0.9600
N4—C9	1.336 (2)	C12—H12C	0.9600
N4—C8	1.3396 (19)	C13—H13A	0.9600
N5—C8	1.3343 (18)	C13—H13B	0.9600
N5—C11	1.340 (2)	C13—H13C	0.9600
N6—C20	1.3183 (18)	C14—C15	1.385 (2)
N6—C14	1.3917 (19)	C14—C19	1.397 (2)
N7—C20	1.3558 (18)	C15—C16	1.380 (2)
N7—C19	1.383 (2)	C15—H15	0.9300
N7—H7	0.87 (1)	C16—C17	1.388 (2)
N8—C20	1.3650 (19)	C16—H16	0.9300
N8—C21	1.3771 (19)	C17—C18	1.383 (2)
N8—H8	0.87 (1)	C17—H17	0.9300
N9—C22	1.3310 (19)	C18—C19	1.384 (2)
N9—C21	1.3367 (19)	C18—H18	0.9300
N10—C21	1.3352 (18)	C22—C23	1.380 (2)
N10—C24	1.3481 (19)	C22—C25	1.498 (2)
C1—C2	1.382 (2)	C23—C24	1.372 (2)
C1—C6	1.396 (2)	C23—H23	0.9300
C2—C3	1.378 (3)	C24—C26	1.496 (2)
C2—H2	0.9300	C25—H25A	0.9600
C3—C4	1.384 (3)	C25—H25B	0.9600
C3—H3A	0.9300	C25—H25C	0.9600
C4—C5	1.382 (2)	C26—H26A	0.9600
C4—H4	0.9300	C26—H26B	0.9600
C5—C6	1.386 (2)	C26—H26C	0.9600

C7—N1—C1	106.87 (13)	C9—C12—H12C	109.5
C7—N1—H1	120.2 (12)	H12A—C12—H12C	109.5
C1—N1—H1	132.8 (12)	H12B—C12—H12C	109.5
C7—N2—C6	104.12 (12)	C11—C13—H13A	109.5
C7—N3—C8	126.91 (13)	C11—C13—H13B	109.5
C7—N3—H3	115.8 (13)	H13A—C13—H13B	109.5
C8—N3—H3	117.0 (13)	C11—C13—H13C	109.5
C9—N4—C8	115.66 (13)	H13A—C13—H13C	109.5
C8—N5—C11	116.23 (13)	H13B—C13—H13C	109.5
C20—N6—C14	104.20 (12)	C15—C14—N6	129.94 (13)
C20—N7—C19	106.69 (12)	C15—C14—C19	119.88 (14)
C20—N7—H7	121.9 (12)	N6—C14—C19	110.18 (13)
C19—N7—H7	131.3 (12)	C16—C15—C14	118.09 (15)
C20—N8—C21	127.59 (13)	C16—C15—H15	121.0
C20—N8—H8	116.5 (13)	C14—C15—H15	121.0
C21—N8—H8	115.9 (12)	C15—C16—C17	121.51 (16)
C22—N9—C21	116.15 (13)	C15—C16—H16	119.2
C21—N10—C24	115.57 (14)	C17—C16—H16	119.2
N1—C1—C2	132.25 (15)	C18—C17—C16	121.25 (15)
N1—C1—C6	105.39 (13)	C18—C17—H17	119.4
C2—C1—C6	122.37 (15)	C16—C17—H17	119.4
C3—C2—C1	116.96 (16)	C17—C18—C19	116.95 (15)
C3—C2—H2	121.5	C17—C18—H18	121.5
C1—C2—H2	121.5	C19—C18—H18	121.5
C2—C3—C4	121.27 (16)	N7—C19—C18	132.51 (14)
C2—C3—H3A	119.4	N7—C19—C14	105.17 (12)
C4—C3—H3A	119.4	C18—C19—C14	122.32 (15)
C5—C4—C3	121.77 (16)	N6—C20—N7	113.75 (13)
C5—C4—H4	119.1	N6—C20—N8	122.52 (13)
C3—C4—H4	119.1	N7—C20—N8	123.73 (13)
C4—C5—C6	117.67 (16)	N10—C21—N9	127.34 (13)
C4—C5—H5	121.2	N10—C21—N8	118.60 (14)
C6—C5—H5	121.2	N9—C21—N8	114.06 (12)
C5—C6—C1	119.94 (14)	N9—C22—C23	120.91 (15)
C5—C6—N2	130.14 (14)	N9—C22—C25	117.17 (14)
C1—C6—N2	109.91 (13)	C23—C22—C25	121.90 (15)
N2—C7—N1	113.70 (13)	C24—C23—C22	119.11 (14)
N2—C7—N3	123.06 (13)	C24—C23—H23	120.4
N1—C7—N3	123.24 (14)	C22—C23—H23	120.4
N5—C8—N4	126.91 (14)	N10—C24—C23	120.91 (14)
N5—C8—N3	118.65 (13)	N10—C24—C26	116.69 (15)
N4—C8—N3	114.42 (13)	C23—C24—C26	122.39 (15)
N4—C9—C10	121.78 (15)	C22—C25—H25A	109.5
N4—C9—C12	116.46 (14)	C22—C25—H25B	109.5
C10—C9—C12	121.74 (15)	H25A—C25—H25B	109.5
C11—C10—C9	118.16 (15)	C22—C25—H25C	109.5
C11—C10—H10	120.9	H25A—C25—H25C	109.5
C9—C10—H10	120.9	H25B—C25—H25C	109.5
N5—C11—C10	121.22 (14)	C24—C26—H26A	109.5
N5—C11—C13	116.37 (15)	C24—C26—H26B	109.5
C10—C11—C13	122.40 (15)	H26A—C26—H26B	109.5
C9—C12—H12A	109.5	C24—C26—H26C	109.5
C9—C12—H12B	109.5	H26A—C26—H26C	109.5
H12A—C12—H12B	109.5	H26B—C26—H26C	109.5

C7—N1—C1—C2	−179.49 (17)	C20—N6—C14—C15	−179.64 (15)
C7—N1—C1—C6	0.26 (16)	C20—N6—C14—C19	0.28 (16)
N1—C1—C2—C3	178.38 (17)	N6—C14—C15—C16	−179.89 (15)
C6—C1—C2—C3	−1.3 (2)	C19—C14—C15—C16	0.2 (2)
C1—C2—C3—C4	0.4 (3)	C14—C15—C16—C17	0.0 (2)
C2—C3—C4—C5	0.7 (3)	C15—C16—C17—C18	0.2 (3)
C3—C4—C5—C6	−0.9 (3)	C16—C17—C18—C19	−0.6 (2)
C4—C5—C6—C1	0.0 (2)	C20—N7—C19—C18	−179.50 (16)
C4—C5—C6—N2	−178.51 (16)	C20—N7—C19—C14	0.38 (16)
N1—C1—C6—C5	−178.65 (14)	C17—C18—C19—N7	−179.37 (15)
C2—C1—C6—C5	1.1 (2)	C17—C18—C19—C14	0.8 (2)
N1—C1—C6—N2	0.17 (17)	C15—C14—C19—N7	179.52 (13)
C2—C1—C6—N2	179.95 (14)	N6—C14—C19—N7	−0.42 (16)
C7—N2—C6—C5	178.13 (16)	C15—C14—C19—C18	−0.6 (2)
C7—N2—C6—C1	−0.53 (16)	N6—C14—C19—C18	179.48 (14)
C6—N2—C7—N1	0.72 (17)	C14—N6—C20—N7	−0.03 (17)
C6—N2—C7—N3	−179.09 (14)	C14—N6—C20—N8	179.56 (13)
C1—N1—C7—N2	−0.64 (18)	C19—N7—C20—N6	−0.23 (17)
C1—N1—C7—N3	179.17 (14)	C19—N7—C20—N8	−179.82 (14)
C8—N3—C7—N2	176.24 (14)	C21—N8—C20—N6	177.63 (14)
C8—N3—C7—N1	−3.6 (3)	C21—N8—C20—N7	−2.8 (3)
C11—N5—C8—N4	−1.6 (2)	C24—N10—C21—N9	0.1 (2)
C11—N5—C8—N3	179.66 (14)	C24—N10—C21—N8	179.65 (13)
C9—N4—C8—N5	0.2 (2)	C22—N9—C21—N10	0.6 (2)
C9—N4—C8—N3	179.02 (13)	C22—N9—C21—N8	−178.95 (13)
C7—N3—C8—N5	3.8 (2)	C20—N8—C21—N10	1.4 (2)
C7—N3—C8—N4	−175.12 (15)	C20—N8—C21—N9	−179.03 (14)
C8—N4—C9—C10	1.5 (2)	C21—N9—C22—C23	−1.1 (2)
C8—N4—C9—C12	−176.69 (15)	C21—N9—C22—C25	177.35 (14)
N4—C9—C10—C11	−1.8 (3)	N9—C22—C23—C24	1.0 (2)
C12—C9—C10—C11	176.30 (16)	C25—C22—C23—C24	−177.42 (16)
C8—N5—C11—C10	1.2 (2)	C21—N10—C24—C23	−0.3 (2)
C8—N5—C11—C13	−179.73 (14)	C21—N10—C24—C26	−179.39 (14)
C9—C10—C11—N5	0.4 (3)	C22—C23—C24—N10	−0.2 (2)
C9—C10—C11—C13	−178.64 (16)	C22—C23—C24—C26	178.81 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃N₅
M_r	239.28
Crystal system, space group	Triclinic, 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)
V (Å³)	1206.94 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13373, 5550, 4124
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.136, 1.01
No. of reflections	5550
No. of parameters	345
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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.

Acknowledgements

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

References

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