Quinolin-3-amine.

In the crystal structur of the achiral title compound, C(9)H(8)N(2), N-H⋯N hydrogen bonds connect the mol-ecules into zigzag chains in [100]. Weak inter-molecular N-H⋯π inter-actions further consolidate the crystal packing.

Related literature

For novel applications of quinolin-3-amine and its derivatives, see: Rohmer et al. (2010 ▶); Kaneshiro et al. (2011 ▶). For the crystal structure of a rhodium coordination compound featuring the title compound as a ligand, see: Garralda et al. (1999 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H8N2

M = 144.17

Orthorhombic,

a = 7.6223 (3) Å

b = 7.6289 (3) Å

c = 12.6967 (4) Å

V = 738.31 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 200 K

0.55 × 0.52 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.950, T max = 0.988

6898 measured reflections

1077 independent reflections

1015 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.091

S = 1.03

1077 reflections

108 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042626/cv5347sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042626/cv5347Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042626/cv5347Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042626/cv5347Isup4.cml

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

C9H8N2	Dx = 1.297 Mg m−3
Mr = 144.17	Melting point = 366–368 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5242 reflections
a = 7.6223 (3) Å	θ = 2.7–28.3°
b = 7.6289 (3) Å	µ = 0.08 mm−1
c = 12.6967 (4) Å	T = 200 K
V = 738.31 (5) Å3	Block, colourless
Z = 4	0.55 × 0.52 × 0.15 mm
F(000) = 304

Bruker APEXII CCD diffractometer	1077 independent reflections
Radiation source: fine-focus sealed tube	1015 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
φ and ω scans	θmax = 28.3°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −6→10
Tmin = 0.950, Tmax = 0.988	k = −9→10
6898 measured reflections	l = −16→16

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.1011P] where P = (Fo2 + 2Fc2)/3
1077 reflections	(Δ/σ)max < 0.001
108 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Refinement. Due to the absence of a strong anomalous scatterer, the Flack parameter is meaningless. Thus, Friedel opposites (737 pairs) have been merged and the item was removed from the CIF.

	x	y	z	Uiso*/Ueq
N1	0.25487 (15)	0.26319 (16)	0.38612 (8)	0.0280 (3)
N2	−0.18546 (17)	0.08305 (19)	0.39280 (11)	0.0359 (3)
H2A	−0.258 (3)	0.023 (3)	0.3568 (15)	0.056 (6)*
H2B	−0.198 (2)	0.098 (3)	0.4628 (17)	0.043 (5)*
C1	0.30327 (17)	0.23241 (17)	0.28353 (9)	0.0249 (3)
C2	0.09884 (17)	0.21121 (18)	0.41581 (9)	0.0277 (3)
H2	0.0663	0.2323	0.4869	0.033*
C3	−0.02593 (17)	0.12565 (16)	0.35016 (9)	0.0253 (3)
C4	0.02155 (18)	0.09412 (17)	0.24707 (10)	0.0265 (3)
H4	−0.0576	0.0376	0.2003	0.032*
C5	0.18933 (16)	0.14693 (17)	0.21189 (9)	0.0244 (3)
C6	0.24840 (19)	0.11883 (19)	0.10713 (10)	0.0299 (3)
H6	0.1743	0.0609	0.0580	0.036*
C7	0.4113 (2)	0.17449 (19)	0.07635 (10)	0.0344 (3)
H7	0.4488	0.1553	0.0059	0.041*
C8	0.52397 (19)	0.2599 (2)	0.14793 (11)	0.0353 (3)
H8	0.6366	0.2982	0.1256	0.042*
C9	0.47097 (17)	0.28794 (19)	0.25005 (11)	0.0313 (3)
H9	0.5474	0.3448	0.2982	0.038*

	U11	U22	U33	U12	U13	U23
N1	0.0323 (5)	0.0323 (6)	0.0193 (5)	−0.0026 (5)	−0.0030 (4)	−0.0003 (4)
N2	0.0318 (6)	0.0443 (7)	0.0316 (6)	−0.0081 (5)	0.0052 (5)	−0.0086 (6)
C1	0.0277 (6)	0.0263 (6)	0.0207 (5)	0.0017 (5)	−0.0018 (5)	0.0009 (5)
C2	0.0340 (6)	0.0299 (6)	0.0191 (5)	−0.0004 (5)	−0.0012 (5)	−0.0007 (5)
C3	0.0279 (6)	0.0238 (5)	0.0243 (6)	0.0009 (5)	−0.0004 (5)	−0.0006 (5)
C4	0.0306 (6)	0.0264 (6)	0.0226 (5)	−0.0013 (5)	−0.0021 (5)	−0.0045 (5)
C5	0.0303 (6)	0.0228 (6)	0.0202 (5)	0.0027 (5)	−0.0006 (5)	−0.0003 (5)
C6	0.0382 (7)	0.0298 (6)	0.0218 (6)	0.0032 (5)	0.0015 (5)	−0.0037 (5)
C7	0.0430 (7)	0.0348 (7)	0.0254 (5)	0.0059 (6)	0.0084 (6)	−0.0008 (5)
C8	0.0320 (6)	0.0389 (7)	0.0350 (7)	0.0010 (6)	0.0070 (6)	0.0052 (6)
C9	0.0294 (7)	0.0347 (7)	0.0298 (6)	−0.0008 (5)	−0.0009 (5)	0.0008 (6)

N1—C2	1.3091 (17)	C4—C5	1.4133 (18)
N1—C1	1.3740 (16)	C4—H4	0.9500
N2—C3	1.3701 (17)	C5—C6	1.4205 (17)
N2—H2A	0.85 (2)	C6—C7	1.369 (2)
N2—H2B	0.90 (2)	C6—H6	0.9500
C1—C9	1.4122 (18)	C7—C8	1.410 (2)
C1—C5	1.4167 (17)	C7—H7	0.9500
C2—C3	1.4231 (17)	C8—C9	1.375 (2)
C2—H2	0.9500	C8—H8	0.9500
C3—C4	1.3792 (17)	C9—H9	0.9500
C2—N1—C1	117.72 (11)	C4—C5—C1	118.88 (11)
C3—N2—H2A	119.4 (14)	C4—C5—C6	122.66 (12)
C3—N2—H2B	116.8 (12)	C1—C5—C6	118.45 (12)
H2A—N2—H2B	122.1 (18)	C7—C6—C5	120.52 (13)
N1—C1—C9	118.50 (12)	C7—C6—H6	119.7
N1—C1—C5	121.52 (12)	C5—C6—H6	119.7
C9—C1—C5	119.98 (11)	C6—C7—C8	120.78 (12)
N1—C2—C3	125.27 (11)	C6—C7—H7	119.6
N1—C2—H2	117.4	C8—C7—H7	119.6
C3—C2—H2	117.4	C9—C8—C7	120.04 (13)
N2—C3—C4	124.50 (12)	C9—C8—H8	120.0
N2—C3—C2	118.07 (11)	C7—C8—H8	120.0
C4—C3—C2	117.42 (12)	C8—C9—C1	120.22 (13)
C3—C4—C5	119.19 (12)	C8—C9—H9	119.9
C3—C4—H4	120.4	C1—C9—H9	119.9
C5—C4—H4	120.4
C2—N1—C1—C9	179.86 (12)	C9—C1—C5—C4	−179.41 (11)
C2—N1—C1—C5	−0.20 (19)	N1—C1—C5—C6	−179.74 (12)
C1—N1—C2—C3	−0.3 (2)	C9—C1—C5—C6	0.20 (18)
N1—C2—C3—N2	−178.55 (13)	C4—C5—C6—C7	179.12 (12)
N1—C2—C3—C4	0.3 (2)	C1—C5—C6—C7	−0.5 (2)
N2—C3—C4—C5	178.95 (12)	C5—C6—C7—C8	0.3 (2)
C2—C3—C4—C5	0.15 (18)	C6—C7—C8—C9	0.1 (2)
C3—C4—C5—C1	−0.61 (18)	C7—C8—C9—C1	−0.4 (2)
C3—C4—C5—C6	179.80 (12)	N1—C1—C9—C8	−179.82 (13)
N1—C1—C5—C4	0.66 (18)	C5—C1—C9—C8	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N1i	0.90 (2)	2.22 (2)	3.0761 (17)	158.2 (18)
N2—H2A···Cgii	0.85 (2)	2.60 (2)	3.3101 (15)	142.3 (19)

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1/C5–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N1i	0.90 (2)	2.22 (2)	3.0761 (17)	158.2 (18)
N2—H2A⋯Cg ii	0.85 (2)	2.60 (2)	3.3101 (15)	142.3 (19)

Symmetry codes: (i) ; (ii) .