Pyridine-3-carboxamidinium chloride.

The title compound, C(6)H(8)N(3) (+)·Cl(-), crystallizes with two formula units in the asymmetric unit. The cations are non-planar with the -C(NH(2))(2) groups twisted relative to the ring planes by 36.7 (3) and 37.8 (3)°. The cations are linked into chains through N-H⋯N hydrogen bonds. N-H⋯Cl hydrogen bonds link the chains into a three-dimensional network.

Related literature

For structures of pyridine-carboxamidinium chlorides, see: Fan et al. (2009 ▶); Chen et al. (2010 ▶).

Experimental

Crystal data

C6H8N3 +·Cl−

M = 157.60

Orthorhombic,

a = 10.9485 (7) Å

b = 33.1581 (14) Å

c = 4.1488 (5) Å

V = 1506.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.40 × 0.35 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.845, T max = 0.930

14201 measured reflections

3213 independent reflections

2953 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.071

S = 1.00

3213 reflections

182 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1246 Friedel pairs

Flack parameter: 0.0019 (5)

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002704/gk2326sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002704/gk2326Isup2.hkl

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

C6H8N3+·Cl−	F(000) = 656
Mr = 157.60	Dx = 1.390 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3213 reflections
a = 10.9485 (7) Å	θ = 3.1–27.5°
b = 33.1581 (14) Å	µ = 0.43 mm−1
c = 4.1488 (5) Å	T = 293 K
V = 1506.1 (2) Å3	Block, colorless
Z = 8	0.40 × 0.35 × 0.17 mm

Rigaku R-AXIS RAPID diffractometer	3213 independent reflections
Radiation source: fine-focus sealed tube	2953 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −14→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −42→42
Tmin = 0.845, Tmax = 0.930	l = −4→5
14201 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.0334P)2 + 0.3352P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.071	(Δ/σ)max = 0.002
S = 1.00	Δρmax = 0.18 e Å−3
3213 reflections	Δρmin = −0.17 e Å−3
182 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.061 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1246 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.0019 (5)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
Cl1	0.80408 (4)	0.549620 (13)	0.75756 (15)	0.05193 (15)
Cl2	0.82982 (4)	0.318730 (12)	0.22533 (15)	0.04986 (15)
N2	0.49341 (12)	0.25905 (4)	1.1812 (4)	0.0384 (3)
H2A	0.5635	0.2541	1.2661	0.046*
H2B	0.4372	0.2409	1.1835	0.046*
N1	0.17495 (13)	0.28055 (4)	0.6167 (4)	0.0392 (4)
N4	0.56768 (13)	0.39520 (4)	0.6649 (4)	0.0427 (4)
C3	0.30154 (15)	0.34172 (5)	0.9320 (5)	0.0359 (4)
H3	0.3444	0.3622	1.0348	0.043*
C2	0.35090 (13)	0.30307 (5)	0.9096 (4)	0.0294 (3)
N3	0.55529 (14)	0.32232 (5)	1.0408 (6)	0.0540 (5)
H3A	0.6261	0.3181	1.1239	0.065*
H3B	0.5390	0.3451	0.9521	0.065*
C1	0.28379 (13)	0.27351 (4)	0.7498 (5)	0.0321 (3)
H1	0.3164	0.2477	0.7352	0.038*
N5	0.93657 (14)	0.40511 (4)	0.3554 (5)	0.0515 (5)
H5A	1.0143	0.4075	0.3329	0.062*
H5B	0.9030	0.3817	0.3431	0.062*
N6	0.91881 (14)	0.47268 (4)	0.4274 (5)	0.0511 (5)
H6A	0.9965	0.4754	0.4053	0.061*
H6B	0.8739	0.4935	0.4622	0.061*
C7	0.68741 (16)	0.40022 (5)	0.6164 (5)	0.0376 (4)
H7	0.7409	0.3809	0.6971	0.045*
C12	0.86919 (16)	0.43713 (5)	0.4083 (5)	0.0366 (4)
C6	0.47248 (14)	0.29402 (5)	1.0493 (5)	0.0328 (3)
C5	0.12821 (16)	0.31783 (5)	0.6479 (5)	0.0448 (5)
H5	0.0512	0.3228	0.5624	0.054*
C8	0.73540 (15)	0.43301 (4)	0.4505 (4)	0.0332 (4)
C4	0.18844 (16)	0.34905 (5)	0.7998 (5)	0.0440 (5)
H4	0.1533	0.3745	0.8126	0.053*
C9	0.65596 (16)	0.46198 (5)	0.3279 (5)	0.0400 (4)
H9	0.6853	0.4846	0.2198	0.048*
C11	0.49241 (17)	0.42297 (5)	0.5413 (5)	0.0432 (4)
H11	0.4089	0.4196	0.5718	0.052*
C10	0.53172 (17)	0.45609 (5)	0.3720 (5)	0.0433 (4)
H10	0.4757	0.4744	0.2879	0.052*

	U11	U22	U33	U12	U13	U23
Cl1	0.0348 (2)	0.0464 (2)	0.0746 (4)	0.00362 (16)	0.0023 (3)	−0.0112 (3)
Cl2	0.0345 (2)	0.03388 (19)	0.0812 (4)	0.00596 (15)	−0.0204 (2)	−0.0130 (2)
N2	0.0260 (6)	0.0361 (7)	0.0531 (10)	−0.0005 (5)	−0.0083 (6)	0.0086 (7)
N1	0.0318 (7)	0.0404 (7)	0.0454 (9)	−0.0045 (6)	−0.0117 (6)	0.0005 (7)
N4	0.0342 (7)	0.0342 (6)	0.0597 (11)	−0.0032 (5)	0.0011 (7)	0.0042 (7)
C3	0.0339 (8)	0.0309 (8)	0.0428 (10)	−0.0015 (6)	−0.0054 (7)	−0.0025 (8)
C2	0.0230 (7)	0.0320 (7)	0.0332 (8)	−0.0020 (6)	−0.0022 (6)	0.0043 (7)
N3	0.0291 (7)	0.0421 (8)	0.0907 (14)	−0.0092 (6)	−0.0213 (8)	0.0190 (9)
C1	0.0292 (7)	0.0307 (7)	0.0363 (9)	−0.0015 (5)	−0.0041 (8)	0.0015 (8)
N5	0.0326 (7)	0.0328 (7)	0.0890 (15)	0.0001 (6)	0.0051 (8)	−0.0079 (8)
N6	0.0359 (8)	0.0336 (7)	0.0837 (14)	−0.0037 (6)	0.0103 (8)	−0.0099 (9)
C7	0.0348 (8)	0.0285 (7)	0.0495 (11)	0.0022 (6)	−0.0024 (7)	0.0008 (8)
C12	0.0347 (8)	0.0318 (7)	0.0433 (10)	0.0002 (6)	0.0015 (7)	−0.0025 (8)
C6	0.0239 (7)	0.0348 (8)	0.0396 (9)	−0.0021 (6)	−0.0046 (7)	0.0004 (7)
C5	0.0281 (8)	0.0510 (10)	0.0552 (13)	0.0046 (7)	−0.0141 (8)	0.0008 (9)
C8	0.0324 (8)	0.0276 (7)	0.0397 (10)	−0.0003 (6)	−0.0010 (7)	−0.0046 (7)
C4	0.0364 (8)	0.0391 (8)	0.0565 (13)	0.0098 (7)	−0.0067 (8)	−0.0020 (9)
C9	0.0413 (9)	0.0313 (7)	0.0473 (12)	0.0021 (7)	−0.0011 (8)	0.0036 (7)
C11	0.0306 (8)	0.0410 (9)	0.0580 (12)	−0.0010 (7)	−0.0038 (8)	−0.0026 (9)
C10	0.0400 (9)	0.0383 (9)	0.0516 (11)	0.0076 (7)	−0.0066 (8)	0.0031 (8)

N2—C6	1.303 (2)	N5—H5A	0.8600
N2—H2A	0.8600	N5—H5B	0.8600
N2—H2B	0.8600	N6—C12	1.300 (2)
N1—C1	1.334 (2)	N6—H6A	0.8600
N1—C5	1.344 (2)	N6—H6B	0.8600
N4—C7	1.337 (2)	C7—C8	1.390 (2)
N4—C11	1.338 (2)	C7—H7	0.9300
C3—C4	1.376 (2)	C12—C8	1.482 (2)
C3—C2	1.394 (2)	C5—C4	1.380 (3)
C3—H3	0.9300	C5—H5	0.9300
C2—C1	1.393 (2)	C8—C9	1.392 (2)
C2—C6	1.483 (2)	C4—H4	0.9300
N3—C6	1.305 (2)	C9—C10	1.386 (3)
N3—H3A	0.8600	C9—H9	0.9300
N3—H3B	0.8600	C11—C10	1.373 (3)
C1—H1	0.9300	C11—H11	0.9300
N5—C12	1.311 (2)	C10—H10	0.9300
C6—N2—H2A	120.0	C8—C7—H7	118.6
C6—N2—H2B	120.0	N6—C12—N5	120.60 (16)
H2A—N2—H2B	120.0	N6—C12—C8	119.31 (15)
C1—N1—C5	117.47 (14)	N5—C12—C8	120.08 (14)
C7—N4—C11	117.45 (16)	N2—C6—N3	121.94 (15)
C4—C3—C2	118.99 (16)	N2—C6—C2	120.16 (14)
C4—C3—H3	120.5	N3—C6—C2	117.88 (15)
C2—C3—H3	120.5	N1—C5—C4	123.50 (16)
C1—C2—C3	118.31 (14)	N1—C5—H5	118.2
C1—C2—C6	121.15 (14)	C4—C5—H5	118.2
C3—C2—C6	120.54 (14)	C7—C8—C9	118.99 (16)
C6—N3—H3A	120.0	C7—C8—C12	120.30 (15)
C6—N3—H3B	120.0	C9—C8—C12	120.71 (15)
H3A—N3—H3B	120.0	C3—C4—C5	118.66 (15)
N1—C1—C2	123.03 (14)	C3—C4—H4	120.7
N1—C1—H1	118.5	C5—C4—H4	120.7
C2—C1—H1	118.5	C10—C9—C8	117.87 (16)
C12—N5—H5A	120.0	C10—C9—H9	121.1
C12—N5—H5B	120.0	C8—C9—H9	121.1
H5A—N5—H5B	120.0	N4—C11—C10	123.61 (17)
C12—N6—H6A	120.0	N4—C11—H11	118.2
C12—N6—H6B	120.0	C10—C11—H11	118.2
H6A—N6—H6B	120.0	C11—C10—C9	119.20 (17)
N4—C7—C8	122.86 (16)	C11—C10—H10	120.4
N4—C7—H7	118.6	C9—C10—H10	120.4
C4—C3—C2—C1	0.8 (3)	N4—C7—C8—C12	179.21 (18)
C4—C3—C2—C6	−179.98 (18)	N6—C12—C8—C7	−141.6 (2)
C5—N1—C1—C2	−1.7 (3)	N5—C12—C8—C7	37.8 (3)
C3—C2—C1—N1	0.2 (3)	N6—C12—C8—C9	37.8 (3)
C6—C2—C1—N1	−178.99 (18)	N5—C12—C8—C9	−142.8 (2)
C11—N4—C7—C8	1.2 (3)	C2—C3—C4—C5	−0.4 (3)
C1—C2—C6—N2	−36.7 (3)	N1—C5—C4—C3	−1.2 (3)
C3—C2—C6—N2	144.10 (19)	C7—C8—C9—C10	−1.4 (3)
C1—C2—C6—N3	144.72 (19)	C12—C8—C9—C10	179.20 (17)
C3—C2—C6—N3	−34.5 (3)	C7—N4—C11—C10	−0.6 (3)
C1—N1—C5—C4	2.1 (3)	N4—C11—C10—C9	−1.0 (3)
N4—C7—C8—C9	−0.2 (3)	C8—C9—C10—C11	1.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···N4	0.86	2.07	2.880 (2)	157
N5—H5B···Cl2	0.86	2.29	3.1403 (15)	170
N6—H6B···Cl1	0.86	2.36	3.1562 (16)	155
N2—H2A···N1i	0.86	2.22	2.990 (2)	149
N2—H2B···Cl2ii	0.86	2.31	3.1452 (13)	165
N3—H3A···Cl2iii	0.86	2.27	3.1040 (16)	164
N5—H5A···Cl1iv	0.86	2.46	3.2373 (16)	150
N6—H6A···Cl1iv	0.86	2.41	3.2013 (16)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯N4	0.86	2.07	2.880 (2)	157
N5—H5B⋯Cl2	0.86	2.29	3.1403 (15)	170
N6—H6B⋯Cl1	0.86	2.36	3.1562 (16)	155
N2—H2A⋯N1i	0.86	2.22	2.990 (2)	149
N2—H2B⋯Cl2ii	0.86	2.31	3.1452 (13)	165
N3—H3A⋯Cl2iii	0.86	2.27	3.1040 (16)	164
N5—H5A⋯Cl1iv	0.86	2.46	3.2373 (16)	150
N6—H6A⋯Cl1iv	0.86	2.41	3.2013 (16)	152

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