2-Amino-4-phenyl-4H,10H-1,3,5-triazino[1,2-a]benzimidazol-3-ium chloride

Mohamed, S.K.; El-Remaily, M.A.A.; Soliman, A.M.; Abdel-Ghany, H.; Ng, S.W.

doi:10.1107/S1600536811013766

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1154

doi:10.1107/S1600536811013766

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2-Amino-4-phenyl-4H,10H-1,3,5-triazino[1,2-a]benzimidazol-3-ium chloride

Shaaban K. Mohamed,^a Mahmoud A. A. El-Remaily,^b Ahmed M. Soliman,^b Hossam Abdel-Ghany ^b and Seik Weng Ng ^c ^*

^aDivision of Chemistry and Environmental Science, Manchester Metropolitan University, Manchester, England, ^bDepartment of Chemistry, Sohag University, Egypt, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 12 April 2011; accepted 12 April 2011; online 16 April 2011)

2-Guanidinobenzimidazole condenses with benzaldehyde in the presence of hydrochloric acid to form 2-amino-3,4-dihydro-4-phenyl-1,3,5-triazino[1,2-a]benzimidazole, which was isolated as its hydrochloride, C₁₅H₁₄N₅⁺·Cl⁻. The positive charge of the cation is formally placed on the double-bonded N atom of the dihydrotriazine ring. The six-membered dihydrotriazine that is fused with the benzimidazole ring system is relatively flat (r.m.s. deviation = 0.106 Å), with the methine C atom deviating most [0.164 (1) Å] from the mean-square plane. The phenyl ring connected to the methine C atom is disordered over two positions in a 0.558 (1):0.442 (1) ratio; the two orientations are aligned at 85.1 (1) and 89.6 (1)° with respect to the dihydrotriazine ring. In the crystal, adjacent cations and anions are linked by N—H⋯N and N—H⋯Cl hydrogen bonds, generating a double chain running along the b axis.

Related literature

For the synthesis, see: Dolzhenko & Chui (2006 ); Martin et al. (1981 ); Nagarajan et al. (1970 ).

Experimental

Crystal data

C₁₅H₁₄N₅⁺·Cl⁻
M_r = 299.76
Triclinic, $[P \overline 1]$
a = 8.6454 (5) Å
b = 9.0440 (4) Å
c = 9.7182 (6) Å
α = 83.306 (4)°
β = 70.956 (5)°
γ = 81.523 (4)°
V = 708.51 (7) Å³
Z = 2
Cu Kα radiation
μ = 2.39 mm⁻¹
T = 100 K
0.20 × 0.20 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.647, T_max = 0.954
7924 measured reflections
2818 independent reflections
2667 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.106
S = 1.01
2818 reflections
237 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.88 (1)	2.23 (1)	3.1033 (16)	172 (2)
N4—H4⋯Cl1ⁱ	0.88 (1)	2.25 (1)	3.1060 (14)	165 (2)
N5—H3⋯N3ⁱⁱ	0.89 (1)	2.08 (1)	2.9643 (19)	176 (2)
N5—H2⋯Cl1ⁱⁱ	0.88 (1)	2.66 (2)	3.3147 (14)	132 (2)
Symmetry codes: (i) x, y-1, z; (ii) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536811013766/bt5515sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013766/bt5515Isup2.hkl

checkCIF report

Comment top

2-Guanidinobenzimidazole and aromatic aldehydes readily condense to form 2-amino-[1,3,5]triazino[1,2-a]benzimidazoles (Nagarajan et al., 1970; Martin et al., 1981); such compounds exhibit dihydrofolate reductase inhibitory activity (Dolzhenko & Chui, 2006). We added acetylacetone in the synthesis as the resulting compound possesses an amino subsitutent that is capable of further condensation, but the hydrochloric acid we used in the synthesis protonated the compound. The positive charge of the salt (Scheme I) is formally placed on the double-bonded N atom of the dihydrotriazine ring. The six-memebered dihydrotriazine that is fused with the benzimidazole ring-system is relatively flat, with the methine C deviating most from the mean-square plane. The phenyl ring that is connected to the methine C atom is disordered over two positions; the two orientations are aligned at nearly 90 ° with respect to the dihydrotriazine ring (Fig. 1). Adjacent cations and anions are linked by N–H···N and N–H···Cl hydrogen bonds to generate a linear chain motif (Table 1).

Related literature top

For the synthesis, see: Dolzhenko & Chui (2006); Martin et al. (1981); Nagarajan et al. (1970).

Experimental top

2-Guanidinobenzimidazole (1H-benzo[d]imidazol-2-yliminomethanediamine) (10 mmol), benzaldehyde (10 mmol) and excess of cyclohexanone (approx. 10 ml) along with few drops of concentrated hydrochloric acid was heated in N,N-dimethylformamide (50 ml) for 30 minutes. The product was collected and recrystallized from ethanol; m.p. 623 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the C₁₅H₁₄N₅ Cl salt at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

2-Amino-4-phenyl-4H,10H-1,3,5- triazino[1,2-a]benzimidazol-3-ium chloride top

Crystal data top

C₁₅H₁₄N₅⁺·Cl⁻	Z = 2
M_r = 299.76	F(000) = 312
Triclinic, P1	D_x = 1.405 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 8.6454 (5) Å	Cell parameters from 4762 reflections
b = 9.0440 (4) Å	θ = 4.8–74.3°
c = 9.7182 (6) Å	µ = 2.39 mm⁻¹
α = 83.306 (4)°	T = 100 K
β = 70.956 (5)°	Plate, colorless
γ = 81.523 (4)°	0.20 × 0.20 × 0.02 mm
V = 708.51 (7) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2818 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2667 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.017
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.5°, θ_min = 4.8°
ω scans	h = −10→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
T_min = 0.647, T_max = 0.954	l = −12→11
7924 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0582P)² + 0.4089P] where P = (F_o² + 2F_c²)/3
2818 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.33 e Å⁻³
6 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₅H₁₄N₅⁺·Cl⁻	γ = 81.523 (4)°
M_r = 299.76	V = 708.51 (7) Å³
Triclinic, P1	Z = 2
a = 8.6454 (5) Å	Cu Kα radiation
b = 9.0440 (4) Å	µ = 2.39 mm⁻¹
c = 9.7182 (6) Å	T = 100 K
α = 83.306 (4)°	0.20 × 0.20 × 0.02 mm
β = 70.956 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2818 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2667 reflections with I > 2σ(I)
T_min = 0.647, T_max = 0.954	R_int = 0.017
7924 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	6 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.33 e Å⁻³
2818 reflections	Δρ_min = −0.29 e Å⁻³
237 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.25096 (5)	0.91819 (4)	0.47166 (4)	0.03322 (14)
N1	0.33424 (18)	0.61809 (16)	0.63707 (17)	0.0319 (3)
N2	0.37251 (16)	0.37732 (15)	0.69693 (15)	0.0279 (3)
N3	0.16136 (17)	0.46368 (14)	0.58756 (15)	0.0274 (3)
N4	0.25040 (18)	0.20531 (15)	0.61885 (15)	0.0297 (3)
N5	0.03987 (18)	0.28598 (15)	0.52257 (16)	0.0305 (3)
C1	0.4578 (2)	0.5963 (2)	0.70333 (19)	0.0341 (4)
C2	0.5488 (2)	0.6965 (3)	0.7323 (2)	0.0464 (5)
H2A	0.5332	0.8008	0.7061	0.056*
C3	0.6639 (3)	0.6360 (3)	0.8014 (2)	0.0587 (7)
H3A	0.7280	0.7009	0.8236	0.070*
C4	0.6878 (3)	0.4836 (3)	0.8389 (3)	0.0588 (7)
H4A	0.7683	0.4470	0.8856	0.071*
C5	0.5980 (2)	0.3834 (3)	0.8102 (2)	0.0465 (5)
H5	0.6144	0.2790	0.8359	0.056*
C6	0.4827 (2)	0.4437 (2)	0.74177 (19)	0.0330 (4)
C7	0.28265 (19)	0.48468 (17)	0.63639 (17)	0.0269 (3)
C8	0.1501 (2)	0.31762 (17)	0.57848 (17)	0.0263 (3)
C9	0.3386 (2)	0.22131 (18)	0.71937 (17)	0.0281 (3)
H9	0.4466	0.1566	0.6891	0.034*	0.558 (7)
H9'	0.4436	0.1519	0.6980	0.034*	0.442 (7)
C10	0.2434 (3)	0.1680 (4)	0.8782 (2)	0.0294 (11)	0.558 (7)
C11	0.0806 (3)	0.2263 (7)	0.9423 (3)	0.0475 (12)	0.558 (7)
H11	0.0253	0.2947	0.8871	0.057*	0.558 (7)
C12	−0.0012 (4)	0.1844 (7)	1.0873 (3)	0.0679 (19)	0.558 (7)
H12	−0.1124	0.2242	1.1311	0.081*	0.558 (7)
C13	0.0798 (7)	0.0843 (5)	1.1681 (2)	0.075 (2)	0.558 (7)
H13	0.0239	0.0557	1.2671	0.090*	0.558 (7)
C14	0.2426 (7)	0.0261 (3)	1.1039 (3)	0.0643 (19)	0.558 (7)
H14	0.2979	−0.0423	1.1591	0.077*	0.558 (7)
C15	0.3244 (5)	0.0679 (3)	0.9590 (3)	0.0408 (12)	0.558 (7)
H15	0.4356	0.0281	0.9151	0.049*	0.558 (7)
C10'	0.2393 (3)	0.1996 (4)	0.8737 (3)	0.0296 (14)	0.442 (7)
C11'	0.1106 (5)	0.3042 (4)	0.9424 (3)	0.0293 (11)	0.442 (7)
H11'	0.0941	0.4001	0.8945	0.035*	0.442 (7)
C12'	0.0060 (4)	0.2685 (4)	1.0813 (3)	0.0397 (13)	0.442 (7)
H12'	−0.0820	0.3400	1.1283	0.048*	0.442 (7)
C13'	0.0302 (4)	0.1282 (4)	1.1515 (3)	0.0356 (13)	0.442 (7)
H13'	−0.0413	0.1038	1.2464	0.043*	0.442 (7)
C14'	0.1589 (5)	0.0236 (3)	1.0827 (5)	0.0375 (12)	0.442 (7)
H14'	0.1755	−0.0723	1.1307	0.045*	0.442 (7)
C15'	0.2635 (4)	0.0592 (3)	0.9438 (4)	0.0342 (12)	0.442 (7)
H15'	0.3515	−0.0123	0.8968	0.041*	0.442 (7)
H1	0.300 (3)	0.7021 (17)	0.594 (2)	0.049 (6)*
H4	0.251 (3)	0.1148 (14)	0.593 (2)	0.042 (6)*
H2	0.020 (3)	0.1933 (13)	0.521 (2)	0.040 (5)*
H3	−0.016 (2)	0.3623 (18)	0.486 (2)	0.043 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0303 (2)	0.0217 (2)	0.0453 (3)	−0.00372 (15)	−0.00500 (17)	−0.01220 (16)
N1	0.0319 (7)	0.0235 (7)	0.0438 (8)	−0.0042 (6)	−0.0128 (6)	−0.0120 (6)
N2	0.0253 (7)	0.0266 (7)	0.0345 (7)	0.0015 (5)	−0.0125 (6)	−0.0097 (5)
N3	0.0302 (7)	0.0172 (6)	0.0394 (7)	−0.0005 (5)	−0.0166 (6)	−0.0060 (5)
N4	0.0415 (8)	0.0186 (6)	0.0338 (7)	0.0019 (6)	−0.0192 (6)	−0.0065 (5)
N5	0.0364 (8)	0.0192 (6)	0.0432 (8)	−0.0051 (6)	−0.0213 (6)	−0.0033 (6)
C1	0.0256 (8)	0.0413 (9)	0.0361 (9)	−0.0060 (7)	−0.0040 (7)	−0.0195 (7)
C2	0.0350 (10)	0.0598 (13)	0.0451 (11)	−0.0182 (9)	0.0006 (8)	−0.0293 (9)
C3	0.0324 (10)	0.100 (2)	0.0505 (12)	−0.0253 (11)	−0.0044 (9)	−0.0371 (13)
C4	0.0336 (11)	0.097 (2)	0.0547 (13)	−0.0087 (11)	−0.0189 (10)	−0.0272 (13)
C5	0.0307 (9)	0.0688 (14)	0.0447 (10)	0.0017 (9)	−0.0170 (8)	−0.0173 (10)
C6	0.0228 (8)	0.0433 (10)	0.0345 (8)	−0.0015 (7)	−0.0071 (7)	−0.0174 (7)
C7	0.0258 (8)	0.0219 (7)	0.0335 (8)	0.0003 (6)	−0.0089 (6)	−0.0099 (6)
C8	0.0304 (8)	0.0191 (7)	0.0308 (8)	−0.0016 (6)	−0.0113 (6)	−0.0038 (6)
C9	0.0282 (8)	0.0274 (8)	0.0285 (8)	0.0023 (6)	−0.0099 (6)	−0.0052 (6)
C10	0.038 (3)	0.031 (2)	0.018 (2)	−0.0146 (15)	−0.0014 (18)	−0.0055 (13)
C11	0.0361 (19)	0.069 (4)	0.0365 (19)	−0.0140 (19)	−0.0019 (15)	−0.0186 (19)
C12	0.064 (3)	0.096 (6)	0.041 (3)	−0.050 (4)	0.010 (2)	−0.018 (3)
C13	0.126 (6)	0.074 (4)	0.028 (2)	−0.071 (4)	−0.003 (3)	−0.003 (3)
C14	0.131 (6)	0.038 (2)	0.0330 (19)	−0.045 (3)	−0.026 (3)	0.0075 (16)
C15	0.073 (3)	0.0228 (16)	0.0333 (17)	−0.0187 (19)	−0.021 (2)	0.0012 (13)
C10'	0.028 (3)	0.027 (2)	0.042 (3)	−0.0030 (17)	−0.019 (3)	−0.0078 (18)
C11'	0.032 (2)	0.029 (2)	0.0245 (18)	0.0022 (18)	−0.0072 (15)	−0.0058 (15)
C12'	0.035 (2)	0.042 (3)	0.035 (2)	0.000 (2)	−0.0032 (18)	−0.007 (2)
C13'	0.032 (2)	0.038 (3)	0.032 (3)	−0.009 (2)	−0.002 (2)	−0.001 (2)
C14'	0.035 (3)	0.029 (2)	0.045 (3)	−0.0102 (18)	−0.010 (2)	0.0078 (19)
C15'	0.027 (2)	0.031 (2)	0.043 (3)	−0.0072 (18)	−0.0083 (19)	0.0000 (19)

Geometric parameters (Å, º) top

N1—C7	1.348 (2)	C9—C10	1.551 (2)
N1—C1	1.397 (2)	C9—H9	1.0000
N1—H1	0.88 (1)	C9—H9'	1.0000
N2—C7	1.355 (2)	C10—C11	1.3900
N2—C6	1.400 (2)	C10—C15	1.3900
N2—C9	1.460 (2)	C11—C12	1.3900
N3—C7	1.329 (2)	C11—H11	0.9500
N3—C8	1.3538 (19)	C12—C13	1.3900
N4—C8	1.344 (2)	C12—H12	0.9500
N4—C9	1.452 (2)	C13—C14	1.3900
N4—H4	0.882 (10)	C13—H13	0.9500
N5—C8	1.319 (2)	C14—C15	1.3900
N5—H2	0.88 (1)	C14—H14	0.9500
N5—H3	0.89 (1)	C15—H15	0.9500
C1—C2	1.390 (2)	C10'—C11'	1.3900
C1—C6	1.391 (3)	C10'—C15'	1.3900
C2—C3	1.389 (3)	C11'—C12'	1.3900
C2—H2A	0.9500	C11'—H11'	0.9500
C3—C4	1.387 (4)	C12'—C13'	1.3900
C3—H3A	0.9500	C12'—H12'	0.9500
C4—C5	1.382 (3)	C13'—C14'	1.3900
C4—H4A	0.9500	C13'—H13'	0.9500
C5—C6	1.386 (3)	C14'—C15'	1.3900
C5—H5	0.9500	C14'—H14'	0.9500
C9—C10'	1.471 (3)	C15'—H15'	0.9500

C7—N1—C1	108.78 (14)	N2—C9—H9	107.9
C7—N1—H1	123.8 (16)	C10'—C9—H9	115.7
C1—N1—H1	127.2 (16)	C10—C9—H9	107.9
C7—N2—C6	109.45 (14)	N4—C9—H9'	110.6
C7—N2—C9	121.34 (13)	N2—C9—H9'	110.7
C6—N2—C9	128.97 (14)	C10'—C9—H9'	110.6
C7—N3—C8	113.66 (13)	C10—C9—H9'	102.7
C8—N4—C9	123.13 (13)	C11—C10—C15	120.0
C8—N4—H4	117.9 (14)	C11—C10—C9	120.27 (17)
C9—N4—H4	118.3 (14)	C15—C10—C9	119.63 (17)
C8—N5—H2	122.4 (14)	C12—C11—C10	120.0
C8—N5—H3	117.3 (14)	C12—C11—H11	120.0
H2—N5—H3	120 (2)	C10—C11—H11	120.0
C2—C1—C6	121.02 (19)	C11—C12—C13	120.0
C2—C1—N1	131.53 (19)	C11—C12—H12	120.0
C6—C1—N1	107.46 (14)	C13—C12—H12	120.0
C1—C2—C3	116.5 (2)	C14—C13—C12	120.0
C1—C2—H2A	121.7	C14—C13—H13	120.0
C3—C2—H2A	121.7	C12—C13—H13	120.0
C4—C3—C2	121.9 (2)	C15—C14—C13	120.0
C4—C3—H3A	119.1	C15—C14—H14	120.0
C2—C3—H3A	119.1	C13—C14—H14	120.0
C5—C4—C3	121.9 (2)	C14—C15—C10	120.0
C5—C4—H4A	119.1	C14—C15—H15	120.0
C3—C4—H4A	119.1	C10—C15—H15	120.0
C4—C5—C6	116.2 (2)	C11'—C10'—C15'	120.0
C4—C5—H5	121.9	C11'—C10'—C9	122.6 (2)
C6—C5—H5	121.9	C15'—C10'—C9	116.8 (2)
C1—C6—C5	122.43 (18)	C12'—C11'—C10'	120.0
C1—C6—N2	105.86 (15)	C12'—C11'—H11'	120.0
C5—C6—N2	131.71 (18)	C10'—C11'—H11'	120.0
N3—C7—N1	125.39 (15)	C11'—C12'—C13'	120.0
N3—C7—N2	126.15 (14)	C11'—C12'—H12'	120.0
N1—C7—N2	108.44 (14)	C13'—C12'—H12'	120.0
N5—C8—N4	119.28 (14)	C14'—C13'—C12'	120.0
N5—C8—N3	118.04 (14)	C14'—C13'—H13'	120.0
N4—C8—N3	122.63 (14)	C12'—C13'—H13'	120.0
N4—C9—N2	105.74 (12)	C15'—C14'—C13'	120.0
N4—C9—C10'	113.24 (18)	C15'—C14'—H14'	120.0
N2—C9—C10'	105.86 (18)	C13'—C14'—H14'	120.0
N4—C9—C10	111.64 (16)	C14'—C15'—C10'	120.0
N2—C9—C10	115.56 (18)	C14'—C15'—H15'	120.0
N4—C9—H9	107.9	C10'—C15'—H15'	120.0

C7—N1—C1—C2	−179.19 (18)	C6—N2—C9—N4	−164.88 (15)
C7—N1—C1—C6	0.91 (19)	C7—N2—C9—C10'	−99.0 (2)
C6—C1—C2—C3	−0.3 (3)	C6—N2—C9—C10'	74.7 (2)
N1—C1—C2—C3	179.83 (18)	C7—N2—C9—C10	−102.57 (19)
C1—C2—C3—C4	0.4 (3)	C6—N2—C9—C10	71.1 (2)
C2—C3—C4—C5	−0.3 (3)	N4—C9—C10—C11	−53.8 (2)
C3—C4—C5—C6	0.0 (3)	N2—C9—C10—C11	67.1 (2)
C2—C1—C6—C5	0.0 (3)	C10'—C9—C10—C11	47.2 (10)
N1—C1—C6—C5	179.93 (16)	N4—C9—C10—C15	129.8 (2)
C2—C1—C6—N2	−179.84 (15)	N2—C9—C10—C15	−109.3 (3)
N1—C1—C6—N2	0.07 (18)	C10'—C9—C10—C15	−129.2 (11)
C4—C5—C6—C1	0.1 (3)	C15—C10—C11—C12	0.0
C4—C5—C6—N2	179.93 (18)	C9—C10—C11—C12	−176.4 (3)
C7—N2—C6—C1	−1.03 (18)	C10—C11—C12—C13	0.0
C9—N2—C6—C1	−175.29 (15)	C11—C12—C13—C14	0.0
C7—N2—C6—C5	179.13 (18)	C12—C13—C14—C15	0.0
C9—N2—C6—C5	4.9 (3)	C13—C14—C15—C10	0.0
C8—N3—C7—N1	170.54 (15)	C11—C10—C15—C14	0.0
C8—N3—C7—N2	−11.2 (2)	C9—C10—C15—C14	176.4 (3)
C1—N1—C7—N3	176.97 (15)	N4—C9—C10'—C11'	−72.3 (3)
C1—N1—C7—N2	−1.56 (18)	N2—C9—C10'—C11'	43.1 (3)
C6—N2—C7—N3	−176.89 (15)	C10—C9—C10'—C11'	−155.5 (11)
C9—N2—C7—N3	−2.1 (2)	N4—C9—C10'—C15'	98.6 (3)
C6—N2—C7—N1	1.62 (18)	N2—C9—C10'—C15'	−146.0 (3)
C9—N2—C7—N1	176.39 (13)	C10—C9—C10'—C15'	15.5 (9)
C9—N4—C8—N5	−160.68 (15)	C15'—C10'—C11'—C12'	0.0
C9—N4—C8—N3	21.9 (2)	C9—C10'—C11'—C12'	170.6 (3)
C7—N3—C8—N5	−175.88 (15)	C10'—C11'—C12'—C13'	0.0
C7—N3—C8—N4	1.6 (2)	C11'—C12'—C13'—C14'	0.0
C8—N4—C9—N2	−31.2 (2)	C12'—C13'—C14'—C15'	0.0
C8—N4—C9—C10'	84.3 (2)	C13'—C14'—C15'—C10'	0.0
C8—N4—C9—C10	95.3 (2)	C11'—C10'—C15'—C14'	0.0
C7—N2—C9—N4	21.46 (19)	C9—C10'—C15'—C14'	−171.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.88 (1)	2.23 (1)	3.1033 (16)	172 (2)
N4—H4···Cl1ⁱ	0.88 (1)	2.25 (1)	3.1060 (14)	165 (2)
N5—H3···N3ⁱⁱ	0.89 (1)	2.08 (1)	2.9643 (19)	176 (2)
N5—H2···Cl1ⁱⁱ	0.88 (1)	2.66 (2)	3.3147 (14)	132 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₅⁺·Cl⁻
M_r	299.76
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.6454 (5), 9.0440 (4), 9.7182 (6)
α, β, γ (°)	83.306 (4), 70.956 (5), 81.523 (4)
V (Å³)	708.51 (7)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.39
Crystal size (mm)	0.20 × 0.20 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.647, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	7924, 2818, 2667
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.106, 1.01
No. of reflections	2818
No. of parameters	237
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.29

Computer programs: CrysAlis PRO (Agilent, 2010), 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···Cl1	0.88 (1)	2.23 (1)	3.1033 (16)	172 (2)
N4—H4···Cl1ⁱ	0.88 (1)	2.25 (1)	3.1060 (14)	165 (2)
N5—H3···N3ⁱⁱ	0.89 (1)	2.08 (1)	2.9643 (19)	176 (2)
N5—H2···Cl1ⁱⁱ	0.88 (1)	2.66 (2)	3.3147 (14)	132 (2)

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

Acknowledgements

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

References

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