8-Quinolylguanidinium chloride.

The title compound, C(10)H(11)N(4) (+)·Cl(-), has been synthesized by the reaction of 8-amino-quinoline and cyanamide. The dihedral angle between the plane of the guanidine group and the quinoline ring system is 68.64 (13)°. The crystal structure is stabilized by inter-molecular N-H⋯Cl hydrogen bonds.

Related literature

For related literature, see: Hughes & Liu (1976 ▶); Juyal & Anand (2003 ▶); Knhla et al. (1986 ▶); Orner & Hamilton (2001 ▶).

Experimental

Crystal data

C10H11N4 +·Cl−

M = 222.68

Orthorhombic,

a = 8.7410 (17) Å

b = 9.0230 (18) Å

c = 13.942 (3) Å

V = 1099.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 293 (2) K

0.20 × 0.20 × 0.20 mm

Data collection

Siemens P4 diffractometer

Absorption correction: multi-scan (XPREP in SHELXTL; Sheldrick, 2008 ▶) T min = 0.939, T max = 0.969

3398 measured reflections

2398 independent reflections

2340 reflections with I > 2σ(I)

R int = 0.0301

3 standard reflections every 97 reflections intensity decay: 2.1%

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.108

S = 0.99

2398 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 500 Friedel pairs

Flack parameter: 0.02 (10)

Data collection: XSCANS (Bruker, 2000 ▶); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013640/rz2213sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013640/rz2213Isup2.hkl

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

C10H11N4+·Cl–	Dx = 1.345 Mg m−3
Mr = 222.68	Melting point = 533–534 K
Orthorhombic, P2(1)2(1)2(1)	Mo Kα radiation λ = 0.71073 Å
a = 8.7410 (17) Å	Cell parameters from 25 reflections
b = 9.0230 (18) Å	θ = 2.1–25.6º
c = 13.942 (3) Å	µ = 0.32 mm−1
V = 1099.6 (4) Å3	T = 293 (2) K
Z = 4	Block, yellow
F000 = 464	0.20 × 0.20 × 0.20 mm

Siemens P4 diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 27.0º
Monochromator: graphite	θmin = 2.7º
T = 293(2) K	h = −11→11
2θ/ω scans	k = −11→11
Absorption correction: multi-scan(XPREP in SHELXTL; Sheldrick, 2008)	l = −17→17
Tmin = 0.939, Tmax = 0.969	3 standard reflections
3398 measured reflections	every 97 reflections
2398 independent reflections	intensity decay: 2.1%
2340 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.585P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.108	(Δ/σ)max = 0.001
S = 0.99	Δρmax = 0.18 e Å−3
2398 reflections	Δρmin = −0.28 e Å−3
136 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 500 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.02 (10)

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	0.87040 (9)	0.86783 (8)	0.66733 (5)	0.04274 (19)
N1	0.7592 (3)	0.9935 (3)	0.97479 (18)	0.0385 (5)
H1A	0.7204	1.0096	1.0305	0.046*
N2	0.8958 (3)	1.1997 (3)	0.99486 (19)	0.0470 (6)
H2A	0.8569	1.2079	1.0513	0.056*
H2B	0.9600	1.2646	0.9745	0.056*
N3	0.9244 (3)	1.0767 (3)	0.85594 (17)	0.0424 (6)
H3A	0.9918	1.1397	0.8371	0.051*
H3B	0.8995	1.0037	0.8195	0.051*
N4	0.4631 (3)	0.9657 (3)	0.90750 (19)	0.0424 (6)
C1	0.7557 (4)	0.6150 (4)	0.8683 (2)	0.0451 (7)
H1	0.8235	0.5370	0.8586	0.054*
C2	0.6087 (3)	0.6031 (3)	0.8407 (2)	0.0435 (7)
H2	0.5741	0.5145	0.8144	0.052*
C3	0.5062 (4)	0.7226 (3)	0.8511 (2)	0.0437 (7)
C4	0.3507 (4)	0.7159 (3)	0.8217 (2)	0.0455 (7)
H4A	0.3118	0.6310	0.7929	0.055*
C5	0.2599 (4)	0.8362 (3)	0.8366 (2)	0.0479 (7)
H5	0.1583	0.8351	0.8169	0.057*
C6	0.3210 (4)	0.9621 (4)	0.8819 (2)	0.0463 (7)
H6	0.2585	1.0436	0.8936	0.056*
C7	0.5564 (4)	0.8547 (4)	0.8952 (2)	0.0426 (7)
C8	0.7119 (3)	0.8643 (4)	0.92611 (19)	0.0398 (6)
C9	0.8061 (4)	0.7491 (3)	0.9126 (2)	0.0434 (7)
H9	0.9072	0.7566	0.9327	0.052*
C10	0.8584 (3)	1.0921 (3)	0.9418 (2)	0.0392 (6)

	U11	U22	U33	U12	U13	U23
Cl1	0.0583 (4)	0.0381 (3)	0.0318 (3)	0.0130 (3)	−0.0029 (3)	0.0014 (3)
N1	0.0418 (13)	0.0343 (12)	0.0395 (12)	−0.0066 (10)	−0.0012 (10)	−0.0012 (10)
N2	0.0490 (15)	0.0475 (15)	0.0445 (14)	−0.0093 (13)	0.0009 (12)	−0.0055 (12)
N3	0.0438 (14)	0.0413 (13)	0.0420 (14)	−0.0112 (11)	0.0029 (10)	−0.0047 (10)
N4	0.0424 (14)	0.0408 (14)	0.0440 (14)	−0.0057 (11)	−0.0028 (11)	0.0004 (11)
C1	0.0506 (17)	0.0380 (17)	0.0468 (15)	−0.0019 (15)	0.0020 (13)	−0.0019 (13)
C2	0.0483 (17)	0.0376 (15)	0.0446 (15)	−0.0059 (12)	0.0004 (14)	−0.0005 (13)
C3	0.0496 (17)	0.0398 (16)	0.0418 (17)	−0.0083 (13)	0.0030 (13)	−0.0009 (13)
C4	0.0478 (17)	0.0423 (15)	0.0464 (16)	−0.0071 (13)	−0.0045 (15)	0.0004 (13)
C5	0.0498 (17)	0.0454 (17)	0.0485 (16)	−0.0079 (14)	−0.0006 (16)	0.0026 (15)
C6	0.0493 (17)	0.0444 (17)	0.0452 (17)	−0.0024 (14)	0.0000 (14)	−0.0008 (13)
C7	0.0456 (16)	0.0396 (16)	0.0426 (15)	−0.0060 (14)	0.0010 (12)	0.0002 (14)
C8	0.0455 (15)	0.0357 (14)	0.0382 (14)	−0.0090 (14)	−0.0028 (12)	0.0011 (13)
C9	0.0460 (16)	0.0379 (15)	0.0462 (16)	−0.0013 (14)	0.0020 (13)	−0.0006 (13)
C10	0.0387 (15)	0.0367 (14)	0.0423 (14)	−0.0079 (12)	−0.0001 (13)	−0.0009 (11)

N1—C10	1.324 (4)	C1—H1	0.9300
N1—C8	1.411 (4)	C2—C3	1.410 (4)
N1—H1A	0.8600	C2—H2	0.9300
N2—C10	1.263 (4)	C3—C7	1.411 (4)
N2—H2A	0.8600	C3—C4	1.420 (4)
N2—H2B	0.8600	C4—C5	1.361 (4)
N3—C10	1.337 (4)	C4—H4A	0.9300
N3—H3A	0.8600	C5—C6	1.406 (4)
N3—H3B	0.8600	C5—H5	0.9300
N4—C6	1.293 (4)	C6—H6	0.9300
N4—C7	1.303 (4)	C7—C8	1.429 (4)
C1—C2	1.345 (5)	C8—C9	1.339 (5)
C1—C9	1.429 (4)	C9—H9	0.9300
C10—N1—C8	125.4 (3)	C5—C4—H4A	120.6
C10—N1—H1A	117.3	C3—C4—H4A	120.6
C8—N1—H1A	117.3	C4—C5—C6	119.5 (3)
C10—N2—H2A	120.0	C4—C5—H5	120.3
C10—N2—H2B	120.0	C6—C5—H5	120.3
H2A—N2—H2B	120.0	N4—C6—C5	120.6 (3)
C10—N3—H3A	120.0	N4—C6—H6	119.7
C10—N3—H3B	120.0	C5—C6—H6	119.7
H3A—N3—H3B	120.0	N4—C7—C3	120.8 (3)
C6—N4—C7	123.1 (3)	N4—C7—C8	120.6 (3)
C2—C1—C9	119.0 (3)	C3—C7—C8	118.6 (3)
C2—C1—H1	120.5	C9—C8—N1	121.9 (3)
C9—C1—H1	120.5	C9—C8—C7	119.7 (3)
C1—C2—C3	121.1 (3)	N1—C8—C7	118.3 (3)
C1—C2—H2	119.4	C8—C9—C1	122.0 (3)
C3—C2—H2	119.4	C8—C9—H9	119.0
C2—C3—C7	119.5 (3)	C1—C9—H9	119.0
C2—C3—C4	123.1 (3)	N2—C10—N1	118.8 (3)
C7—C3—C4	117.3 (3)	N2—C10—N3	119.5 (3)
C5—C4—C3	118.7 (3)	N1—C10—N3	121.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.86	2.34	3.171 (3)	162
N2—H2A···Cl1i	0.86	2.65	3.401 (3)	146
N2—H2B···Cl1ii	0.86	2.64	3.405 (3)	149
N3—H3A···Cl1ii	0.86	2.39	3.198 (3)	158
N3—H3B···Cl1	0.86	2.46	3.269 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.86	2.34	3.171 (3)	162
N2—H2A⋯Cl1i	0.86	2.65	3.401 (3)	146
N2—H2B⋯Cl1ii	0.86	2.64	3.405 (3)	149
N3—H3A⋯Cl1ii	0.86	2.39	3.198 (3)	158
N3—H3B⋯Cl1	0.86	2.46	3.269 (3)	156

Symmetry codes: (i) ; (ii) .