2,4-Diamino-6-methyl-1,3,5-triazin-1-ium chloride.

In the title compound, C(4)H(8)N(5) (+)·Cl(-), a two-dimensional layer packing network is observed in which every chloride anion links three adjacent 2,4-diamino-6-methyl-1,3,5-triazin-1-ium cations by N-H⋯Cl hydrogen-bonding inter-actions, forming 12-membered and eight-membered hydrogen-bonded rings with graph-set motifs R(4) (4)(12) and R(3) (3)(8), respectively. In addition, N-H⋯N hydrogen bonds are found between adjacent cations, forming another type of eight-membered [R(2) (2)(8)] hydrogen-bonded ring.

Related literature

For related complexes, see Delori et al. (2008 ▶); Fan et al. (2009 ▶); Perpétuo & Janczak (2007 ▶); Portalone & Colapietro (2007 ▶); Wijaya et al. (2004 ▶).

Experimental

Crystal data

C4H8N5 +·Cl−

M = 161.60

Triclinic,

a = 5.6449 (11) Å

b = 7.8723 (15) Å

c = 9.3476 (17) Å

α = 65.551 (3)°

β = 75.779 (2)°

γ = 71.027 (2)°

V = 354.61 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.47 mm−1

T = 291 K

0.16 × 0.14 × 0.10 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.929, T max = 0.955

1871 measured reflections

1303 independent reflections

1042 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.07

1303 reflections

96 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007907/nk2023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007907/nk2023Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C4H8N5+·Cl−	Z = 2
Mr = 161.60	F(000) = 168
Triclinic, P1	Dx = 1.513 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6449 (11) Å	Cell parameters from 890 reflections
b = 7.8723 (15) Å	θ = 2.4–28.0°
c = 9.3476 (17) Å	µ = 0.47 mm−1
α = 65.551 (3)°	T = 291 K
β = 75.779 (2)°	Block, colourless
γ = 71.027 (2)°	0.16 × 0.14 × 0.10 mm
V = 354.61 (12) Å3

Bruker SMART 1K CCD area-detector diffractometer	1303 independent reflections
Radiation source: sealed tube	1042 reflections with I > 2σ(I)
graphite	Rint = 0.082
ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.929, Tmax = 0.955	k = −9→8
1871 measured reflections	l = −11→11

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0566P)2] where P = (Fo2 + 2Fc2)/3
1303 reflections	(Δ/σ)max < 0.001
96 parameters	Δρmax = 0.25 e Å−3
2 restraints	Δρmin = −0.28 e Å−3

Experimental. The structure was solved by direct methods (Bruker, 2007) and successive difference Fourier syntheses.

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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.4096 (5)	0.1560 (3)	0.7585 (3)	0.0347 (6)
C2	0.2148 (4)	0.2118 (3)	0.9841 (3)	0.0321 (5)
C3	0.5223 (4)	0.3642 (3)	0.8366 (3)	0.0328 (6)
C4	0.4508 (5)	0.0666 (4)	0.6414 (3)	0.0458 (7)
H4A	0.4399	−0.0647	0.6949	0.069*
H4B	0.6152	0.0696	0.5817	0.069*
H4C	0.3244	0.1365	0.5709	0.069*
Cl1	1.09342 (12)	0.67148 (10)	0.58725 (8)	0.0492 (3)
N1	0.2385 (4)	0.1200 (3)	0.8830 (2)	0.0375 (5)
N2	0.3507 (4)	0.3320 (3)	0.9661 (2)	0.0338 (5)
N3	0.5556 (4)	0.2746 (3)	0.7331 (2)	0.0351 (5)
N4	0.0432 (4)	0.1740 (3)	1.1080 (2)	0.0433 (6)
H4D	0.0189	0.2262	1.1767	0.052*
H4E	−0.0452	0.0969	1.1205	0.052*
N5	0.6634 (4)	0.4803 (3)	0.8085 (2)	0.0443 (6)
H5A	0.6466	0.5365	0.8733	0.053*
H5B	0.7731	0.5003	0.7252	0.053*
H3	0.654 (4)	0.297 (4)	0.6445 (19)	0.058 (9)*

	U11	U22	U33	U12	U13	U23
C1	0.0390 (14)	0.0376 (13)	0.0335 (13)	−0.0099 (11)	0.0005 (10)	−0.0214 (10)
C2	0.0379 (13)	0.0339 (12)	0.0281 (12)	−0.0104 (10)	0.0016 (10)	−0.0170 (10)
C3	0.0378 (13)	0.0349 (12)	0.0309 (12)	−0.0106 (10)	−0.0010 (10)	−0.0177 (10)
C4	0.0544 (17)	0.0604 (17)	0.0401 (14)	−0.0242 (14)	0.0072 (12)	−0.0352 (13)
Cl1	0.0474 (5)	0.0639 (5)	0.0421 (4)	−0.0230 (3)	0.0105 (3)	−0.0272 (3)
N1	0.0442 (13)	0.0421 (12)	0.0352 (12)	−0.0180 (10)	0.0051 (10)	−0.0232 (9)
N2	0.0400 (12)	0.0386 (11)	0.0303 (10)	−0.0161 (9)	0.0038 (9)	−0.0198 (9)
N3	0.0403 (12)	0.0403 (11)	0.0312 (11)	−0.0145 (10)	0.0053 (9)	−0.0216 (9)
N4	0.0524 (13)	0.0533 (13)	0.0392 (12)	−0.0276 (11)	0.0114 (10)	−0.0300 (10)
N5	0.0539 (14)	0.0555 (13)	0.0393 (12)	−0.0311 (11)	0.0121 (10)	−0.0294 (10)

C1—N1	1.311 (3)	C4—H4A	0.9600
C1—N3	1.352 (3)	C4—H4B	0.9600
C1—C4	1.468 (3)	C4—H4C	0.9600
C2—N4	1.312 (3)	N3—H3	0.862 (11)
C2—N2	1.337 (3)	N4—H4D	0.8600
C2—N1	1.369 (3)	N4—H4E	0.8600
C3—N5	1.308 (3)	N5—H5A	0.8600
C3—N2	1.341 (3)	N5—H5B	0.8600
C3—N3	1.363 (3)
N1—C1—N3	122.0 (2)	H4A—C4—H4C	109.5
N1—C1—C4	120.7 (2)	H4B—C4—H4C	109.5
N3—C1—C4	117.3 (2)	C1—N1—C2	115.85 (19)
N4—C2—N2	119.4 (2)	C2—N2—C3	116.07 (18)
N4—C2—N1	115.07 (19)	C1—N3—C3	119.81 (19)
N2—C2—N1	125.6 (2)	C1—N3—H3	115 (2)
N5—C3—N2	120.5 (2)	C3—N3—H3	124 (2)
N5—C3—N3	118.8 (2)	C2—N4—H4D	120.0
N2—C3—N3	120.7 (2)	C2—N4—H4E	120.0
C1—C4—H4A	109.5	H4D—N4—H4E	120.0
C1—C4—H4B	109.5	C3—N5—H5A	120.0
H4A—C4—H4B	109.5	C3—N5—H5B	120.0
C1—C4—H4C	109.5	H5A—N5—H5B	120.0
N3—C1—N1—C2	0.9 (3)	N5—C3—N2—C2	179.7 (2)
C4—C1—N1—C2	−179.6 (2)	N3—C3—N2—C2	−1.3 (3)
N4—C2—N1—C1	−179.9 (2)	N1—C1—N3—C3	−1.6 (4)
N2—C2—N1—C1	−0.3 (3)	C4—C1—N3—C3	178.8 (2)
N4—C2—N2—C3	−179.9 (2)	N5—C3—N3—C1	−179.1 (2)
N1—C2—N2—C3	0.6 (3)	N2—C3—N3—C1	1.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cl1i	0.86 (1)	2.25 (1)	3.107 (2)	174 (3)
N4—H4D···Cl1ii	0.86	2.52	3.372 (2)	169
N4—H4E···N1iii	0.86	2.32	3.171 (3)	170
N5—H5A···N2ii	0.86	2.15	3.008 (3)	174
N5—H5B···Cl1	0.86	2.40	3.125 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Cl1i	0.86 (1)	2.25 (1)	3.107 (2)	174 (3)
N4—H4D⋯Cl1ii	0.86	2.52	3.372 (2)	169
N4—H4E⋯N1iii	0.86	2.32	3.171 (3)	170
N5—H5A⋯N2ii	0.86	2.15	3.008 (3)	174
N5—H5B⋯Cl1	0.86	2.40	3.125 (2)	143

Symmetry codes: (i) ; (ii) ; (iii) .