Pyridine-4-carboximidamidate chloride.

In the title salt, C(6)H(8)N(3) (+)·Cl(-), each pyridine-carbox-imid-amidate cation is linked to two symmetry-related cations through N-H⋯N hydrogen bonds, and to two chloride ions by N-H⋯Cl hydrogen bonds. The N-H⋯N hydrogen bonds involve the pyridine N atom and one NH(2) group. In the crystal, N-H⋯N and N-H⋯Cl hydrogen bonds extend the structure into two-dimensional layers. Weak C-H⋯Cl inter-actions further connect these layers into a three-dimensional network.

Related literature

For background, see: Chudinov et al. (2005 ▶); Kamei et al. (2005 ▶).

Experimental

Crystal data

C6H8N3 +·Cl−

M = 157.60

Orthorhombic,

a = 7.3928 (13) Å

b = 10.4467 (16) Å

c = 18.925 (3) Å

V = 1461.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.44 mm−1

T = 293 K

0.37 × 0.32 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.853, T max = 0.911

1949 measured reflections

1435 independent reflections

1215 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.092

S = 1.04

1435 reflections

124 parameters

All H-atom parameters refined

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903517X/bh2242sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903517X/bh2242Isup2.hkl

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

C6H8N3+·Cl−	F(000) = 656
Mr = 157.60	Dx = 1.432 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 542 reflections
a = 7.3928 (13) Å	θ = 2.3–22.8°
b = 10.4467 (16) Å	µ = 0.44 mm−1
c = 18.925 (3) Å	T = 293 K
V = 1461.6 (4) Å3	Block, colourless
Z = 8	0.37 × 0.32 × 0.21 mm

Bruker SMART CCD area-detector diffractometer	1435 independent reflections
Radiation source: fine-focus sealed tube	1215 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→1
Tmin = 0.853, Tmax = 0.911	k = −1→12
1949 measured reflections	l = −23→1

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	All H-atom parameters refined
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0416P)2 + 0.5489P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
1435 reflections	Δρmax = 0.23 e Å−3
124 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0056 (15)

	x	y	z	Uiso*/Ueq
N1	0.0852 (2)	0.38353 (14)	0.75509 (8)	0.0367 (4)
C1	0.0499 (3)	0.36114 (17)	0.82329 (10)	0.0367 (4)
Cl1	0.15740 (8)	0.91636 (4)	1.05546 (2)	0.0432 (2)
N2	0.0353 (2)	0.79417 (15)	0.89141 (9)	0.0369 (4)
C2	0.0593 (3)	0.45387 (17)	0.87518 (9)	0.0341 (4)
N3	0.1766 (3)	0.66264 (17)	0.97084 (9)	0.0428 (4)
C3	0.1026 (2)	0.57807 (15)	0.85578 (9)	0.0285 (4)
C4	0.1401 (3)	0.60305 (17)	0.78520 (9)	0.0337 (4)
C5	0.1315 (3)	0.50297 (18)	0.73774 (9)	0.0376 (4)
C6	0.1052 (2)	0.68338 (16)	0.90895 (9)	0.0310 (4)
H4	0.171 (3)	0.6863 (18)	0.7679 (10)	0.033 (5)*
H1	0.015 (3)	0.275 (2)	0.8348 (11)	0.044 (6)*
H2	0.032 (3)	0.4327 (18)	0.9204 (11)	0.041 (5)*
H5	0.159 (3)	0.519 (2)	0.6925 (12)	0.048 (6)*
H2B	0.037 (3)	0.854 (2)	0.9202 (13)	0.060 (7)*
H2A	−0.016 (3)	0.803 (2)	0.8500 (12)	0.050 (6)*
H3B	0.229 (4)	0.590 (2)	0.9833 (12)	0.056 (7)*
H3A	0.184 (3)	0.732 (2)	1.0012 (14)	0.061 (7)*

	U11	U22	U33	U12	U13	U23
N1	0.0452 (9)	0.0312 (8)	0.0338 (8)	0.0019 (7)	0.0001 (7)	−0.0051 (7)
C1	0.0439 (11)	0.0261 (9)	0.0400 (10)	−0.0002 (8)	−0.0007 (9)	0.0007 (7)
Cl1	0.0580 (3)	0.0357 (3)	0.0359 (3)	0.0007 (2)	−0.0055 (2)	−0.00566 (18)
N2	0.0484 (10)	0.0262 (8)	0.0360 (9)	0.0009 (7)	0.0006 (8)	−0.0043 (7)
C2	0.0436 (11)	0.0306 (9)	0.0280 (9)	0.0035 (8)	0.0027 (8)	0.0019 (7)
N3	0.0613 (12)	0.0348 (9)	0.0323 (8)	0.0070 (8)	−0.0090 (8)	−0.0067 (7)
C3	0.0313 (9)	0.0266 (8)	0.0277 (8)	0.0021 (7)	−0.0020 (7)	−0.0021 (7)
C4	0.0421 (10)	0.0280 (9)	0.0310 (9)	−0.0020 (8)	0.0003 (8)	0.0024 (7)
C5	0.0488 (12)	0.0377 (10)	0.0264 (9)	−0.0002 (8)	0.0022 (8)	−0.0012 (8)
C6	0.0348 (9)	0.0280 (9)	0.0300 (9)	−0.0018 (7)	0.0031 (7)	−0.0020 (7)

N1—C5	1.335 (2)	N3—C6	1.303 (2)
N1—C1	1.337 (2)	N3—H3B	0.89 (2)
C1—C2	1.381 (3)	N3—H3A	0.93 (3)
C1—H1	0.96 (2)	C3—C4	1.389 (2)
N2—C6	1.310 (2)	C3—C6	1.491 (2)
N2—H2B	0.83 (3)	C4—C5	1.380 (3)
N2—H2A	0.88 (2)	C4—H4	0.958 (19)
C2—C3	1.386 (2)	C5—H5	0.90 (2)
C2—H2	0.91 (2)
C5—N1—C1	116.80 (15)	C2—C3—C4	118.47 (16)
N1—C1—C2	123.63 (17)	C2—C3—C6	120.99 (15)
N1—C1—H1	115.7 (12)	C4—C3—C6	120.52 (15)
C2—C1—H1	120.6 (12)	C5—C4—C3	118.33 (17)
C6—N2—H2B	119.8 (17)	C5—C4—H4	118.5 (11)
C6—N2—H2A	119.2 (15)	C3—C4—H4	123.2 (11)
H2B—N2—H2A	121 (2)	N1—C5—C4	124.05 (17)
C1—C2—C3	118.68 (16)	N1—C5—H5	118.2 (15)
C1—C2—H2	119.3 (13)	C4—C5—H5	117.7 (15)
C3—C2—H2	122.0 (13)	N3—C6—N2	122.31 (17)
C6—N3—H3B	123.9 (15)	N3—C6—C3	119.28 (16)
C6—N3—H3A	116.9 (16)	N2—C6—C3	118.41 (16)
H3B—N3—H3A	119 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.88 (2)	2.22 (2)	3.058 (2)	160 (2)
N3—H3A···Cl1	0.93 (2)	2.19 (2)	3.100 (2)	167 (2)
N2—H2B···Cl1	0.83 (2)	2.79 (2)	3.476 (2)	142 (2)
N3—H3B···Cl1ii	0.89 (2)	2.41 (2)	3.270 (2)	161 (2)
C5—H5···Cl1iii	0.90 (2)	2.68 (2)	3.556 (2)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.88 (2)	2.22 (2)	3.058 (2)	160 (2)
N2—H2B⋯Cl1	0.83 (2)	2.79 (2)	3.476 (2)	142 (2)
N3—H3A⋯Cl1	0.93 (2)	2.19 (2)	3.100 (2)	167 (2)
N3—H3B⋯Cl1ii	0.89 (2)	2.41 (2)	3.270 (2)	161 (2)
C5—H5⋯Cl1iii	0.90 (2)	2.68 (2)	3.556 (2)	166 (2)

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