1-Isobutyl-N,N-dimethyl-1H-imidazo[4,5-c]quinolin-4-amine.

In the title compound, C(16)H(20)N(4), the 1H-imidazo[4,5-c]quinoline ring system is approximately planar, with a maximum deviation of 0.0719 (15) Å. An intra-molecular C-H⋯N hydrogen bond contributes to the stabilization of the mol-ecule, forming an S(6) ring motif. In the crystal, the mol-ecules are stacked along the b axis through weak aromatic π-π inter-actions between benzene and imidazole and benzene and pyridine rings [centroid-centroid distances = 3.6055 (10) and 3.5342 (10) Å, respectively].

Related literature

For background to quinolines and their microbial activity, see: Jampilek et al. (2005 ▶); Gershon et al. (2004 ▶); Dardari et al. (2004 ▶). For the syntheses of 1H-imidazo[4,5-c]quinolin-4-amines, see: Gabriel (1918 ▶); Izumi et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H20N4

M = 268.36

Monoclinic,

a = 9.2804 (2) Å

b = 18.5492 (6) Å

c = 8.5147 (2) Å

β = 101.051 (2)°

V = 1438.57 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.39 × 0.29 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.989

13134 measured reflections

3456 independent reflections

2271 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.146

S = 1.02

3456 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100153X/is2656sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100153X/is2656Isup2.hkl

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

C16H20N4	F(000) = 576
Mr = 268.36	Dx = 1.239 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3031 reflections
a = 9.2804 (2) Å	θ = 2.2–27.4°
b = 18.5492 (6) Å	µ = 0.08 mm−1
c = 8.5147 (2) Å	T = 296 K
β = 101.051 (2)°	Block, colourless
V = 1438.57 (7) Å3	0.39 × 0.29 × 0.14 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3456 independent reflections
Radiation source: fine-focus sealed tube	2271 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.971, Tmax = 0.989	k = −19→24
13134 measured reflections	l = −10→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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0604P)2 + 0.3608P] where P = (Fo2 + 2Fc2)/3
3456 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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
N1	0.44302 (15)	0.08084 (8)	0.74563 (17)	0.0430 (4)
N3	0.31258 (17)	0.18631 (8)	0.3740 (2)	0.0512 (4)
N2	0.51431 (15)	0.14182 (8)	0.30069 (17)	0.0418 (4)
N4	0.22238 (16)	0.14021 (9)	0.68830 (19)	0.0520 (4)
C7	0.35046 (18)	0.12102 (9)	0.6440 (2)	0.0400 (4)
C6	0.57198 (17)	0.05715 (9)	0.7062 (2)	0.0386 (4)
C5	0.66567 (19)	0.01562 (10)	0.8208 (2)	0.0467 (5)
H5A	0.6387	0.0059	0.9184	0.056*
C4	0.7957 (2)	−0.01084 (11)	0.7918 (2)	0.0500 (5)
H4A	0.8563	−0.0378	0.8698	0.060*
C3	0.8376 (2)	0.00247 (10)	0.6460 (2)	0.0499 (5)
H3A	0.9262	−0.0155	0.6269	0.060*
C2	0.74870 (18)	0.04200 (9)	0.5307 (2)	0.0428 (4)
H2A	0.7771	0.0500	0.4333	0.051*
C1	0.61517 (17)	0.07070 (8)	0.55699 (19)	0.0358 (4)
C9	0.51360 (17)	0.11474 (8)	0.45202 (19)	0.0363 (4)
C8	0.38711 (18)	0.14192 (9)	0.4938 (2)	0.0395 (4)
C10	0.3921 (2)	0.18403 (10)	0.2632 (2)	0.0510 (5)
H10A	0.3677	0.2090	0.1670	0.061*
C11	0.61699 (19)	0.12704 (10)	0.1942 (2)	0.0449 (4)
H11A	0.5682	0.1362	0.0848	0.054*
H11B	0.6434	0.0764	0.2024	0.054*
C12	0.7563 (2)	0.17189 (10)	0.2307 (2)	0.0466 (4)
H12A	0.7980	0.1669	0.3450	0.056*
C13	0.8672 (2)	0.14245 (12)	0.1367 (3)	0.0684 (6)
H13A	0.8840	0.0923	0.1609	0.103*
H13B	0.9579	0.1684	0.1657	0.103*
H13C	0.8298	0.1481	0.0242	0.103*
C14	0.7246 (3)	0.25132 (11)	0.1958 (3)	0.0689 (6)
H14A	0.8137	0.2785	0.2254	0.103*
H14B	0.6539	0.2680	0.2564	0.103*
H14C	0.6862	0.2576	0.0837	0.103*
C15	0.1048 (2)	0.17851 (13)	0.5909 (3)	0.0690 (6)
H15A	0.1212	0.1807	0.4830	0.103*
H15B	0.1002	0.2265	0.6318	0.103*
H15C	0.0139	0.1540	0.5923	0.103*
C16	0.1954 (2)	0.11825 (15)	0.8435 (3)	0.0716 (7)
H16A	0.2865	0.1175	0.9193	0.107*
H16B	0.1527	0.0709	0.8355	0.107*
H16C	0.1292	0.1517	0.8784	0.107*

	U11	U22	U33	U12	U13	U23
N1	0.0436 (8)	0.0471 (8)	0.0387 (8)	0.0035 (7)	0.0084 (6)	−0.0017 (7)
N3	0.0483 (8)	0.0502 (9)	0.0556 (10)	0.0094 (7)	0.0110 (7)	0.0128 (8)
N2	0.0434 (8)	0.0424 (8)	0.0401 (8)	−0.0001 (6)	0.0093 (6)	0.0054 (7)
N4	0.0468 (8)	0.0622 (10)	0.0497 (10)	0.0129 (8)	0.0161 (7)	0.0038 (8)
C7	0.0396 (9)	0.0384 (9)	0.0425 (10)	−0.0003 (7)	0.0089 (7)	−0.0055 (8)
C6	0.0388 (8)	0.0368 (9)	0.0395 (9)	−0.0017 (7)	0.0058 (7)	−0.0033 (7)
C5	0.0525 (11)	0.0512 (11)	0.0354 (10)	0.0042 (9)	0.0062 (8)	0.0028 (8)
C4	0.0479 (10)	0.0540 (11)	0.0456 (11)	0.0095 (9)	0.0023 (8)	0.0075 (9)
C3	0.0428 (10)	0.0512 (11)	0.0568 (12)	0.0086 (8)	0.0126 (8)	0.0068 (9)
C2	0.0446 (9)	0.0405 (9)	0.0453 (10)	0.0015 (8)	0.0137 (8)	0.0049 (8)
C1	0.0376 (8)	0.0309 (8)	0.0385 (9)	−0.0022 (7)	0.0064 (7)	−0.0010 (7)
C9	0.0410 (9)	0.0311 (8)	0.0367 (9)	−0.0036 (7)	0.0069 (7)	0.0000 (7)
C8	0.0400 (9)	0.0342 (8)	0.0432 (10)	0.0001 (7)	0.0052 (7)	0.0016 (8)
C10	0.0502 (10)	0.0514 (11)	0.0508 (11)	0.0071 (9)	0.0080 (9)	0.0145 (9)
C11	0.0500 (10)	0.0485 (10)	0.0368 (10)	0.0018 (8)	0.0100 (8)	0.0018 (8)
C12	0.0483 (10)	0.0483 (10)	0.0449 (10)	0.0000 (8)	0.0132 (8)	0.0083 (8)
C13	0.0610 (13)	0.0689 (14)	0.0824 (16)	0.0028 (11)	0.0312 (12)	0.0030 (13)
C14	0.0788 (15)	0.0514 (12)	0.0844 (17)	−0.0004 (11)	0.0352 (13)	0.0129 (12)
C15	0.0460 (11)	0.0844 (16)	0.0790 (16)	0.0166 (11)	0.0183 (10)	0.0156 (13)
C16	0.0606 (13)	0.1034 (19)	0.0566 (13)	0.0146 (12)	0.0256 (11)	0.0048 (13)

N1—C7	1.325 (2)	C1—C9	1.425 (2)
N1—C6	1.376 (2)	C9—C8	1.385 (2)
N3—C10	1.305 (2)	C10—H10A	0.9300
N3—C8	1.388 (2)	C11—C12	1.519 (3)
N2—C10	1.365 (2)	C11—H11A	0.9700
N2—C9	1.384 (2)	C11—H11B	0.9700
N2—C11	1.461 (2)	C12—C14	1.521 (3)
N4—C7	1.361 (2)	C12—C13	1.521 (3)
N4—C15	1.427 (2)	C12—H12A	0.9800
N4—C16	1.450 (2)	C13—H13A	0.9600
C7—C8	1.439 (2)	C13—H13B	0.9600
C6—C5	1.406 (2)	C13—H13C	0.9600
C6—C1	1.426 (2)	C14—H14A	0.9600
C5—C4	1.368 (2)	C14—H14B	0.9600
C5—H5A	0.9300	C14—H14C	0.9600
C4—C3	1.393 (3)	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C3—C2	1.368 (2)	C15—H15C	0.9600
C3—H3A	0.9300	C16—H16A	0.9600
C2—C1	1.405 (2)	C16—H16B	0.9600
C2—H2A	0.9300	C16—H16C	0.9600
C7—N1—C6	120.37 (15)	N2—C10—H10A	122.9
C10—N3—C8	103.93 (14)	N2—C11—C12	113.65 (15)
C10—N2—C9	105.91 (14)	N2—C11—H11A	108.8
C10—N2—C11	125.01 (15)	C12—C11—H11A	108.8
C9—N2—C11	129.00 (14)	N2—C11—H11B	108.8
C7—N4—C15	125.46 (16)	C12—C11—H11B	108.8
C7—N4—C16	119.42 (16)	H11A—C11—H11B	107.7
C15—N4—C16	115.06 (16)	C11—C12—C14	111.44 (16)
N1—C7—N4	117.22 (16)	C11—C12—C13	109.34 (16)
N1—C7—C8	119.85 (15)	C14—C12—C13	111.73 (17)
N4—C7—C8	122.93 (16)	C11—C12—H12A	108.1
N1—C6—C5	117.17 (15)	C14—C12—H12A	108.1
N1—C6—C1	124.58 (15)	C13—C12—H12A	108.1
C5—C6—C1	118.24 (15)	C12—C13—H13A	109.5
C4—C5—C6	121.37 (17)	C12—C13—H13B	109.5
C4—C5—H5A	119.3	H13A—C13—H13B	109.5
C6—C5—H5A	119.3	C12—C13—H13C	109.5
C5—C4—C3	120.26 (17)	H13A—C13—H13C	109.5
C5—C4—H4A	119.9	H13B—C13—H13C	109.5
C3—C4—H4A	119.9	C12—C14—H14A	109.5
C2—C3—C4	120.10 (17)	C12—C14—H14B	109.5
C2—C3—H3A	119.9	H14A—C14—H14B	109.5
C4—C3—H3A	119.9	C12—C14—H14C	109.5
C3—C2—C1	121.20 (16)	H14A—C14—H14C	109.5
C3—C2—H2A	119.4	H14B—C14—H14C	109.5
C1—C2—H2A	119.4	N4—C15—H15A	109.5
C2—C1—C9	127.93 (15)	N4—C15—H15B	109.5
C2—C1—C6	118.81 (15)	H15A—C15—H15B	109.5
C9—C1—C6	113.24 (14)	N4—C15—H15C	109.5
N2—C9—C8	105.21 (14)	H15A—C15—H15C	109.5
N2—C9—C1	132.15 (15)	H15B—C15—H15C	109.5
C8—C9—C1	122.60 (15)	N4—C16—H16A	109.5
C9—C8—N3	110.77 (15)	N4—C16—H16B	109.5
C9—C8—C7	119.13 (15)	H16A—C16—H16B	109.5
N3—C8—C7	130.09 (15)	N4—C16—H16C	109.5
N3—C10—N2	114.14 (16)	H16A—C16—H16C	109.5
N3—C10—H10A	122.9	H16B—C16—H16C	109.5
C6—N1—C7—N4	177.51 (15)	C11—N2—C9—C1	6.5 (3)
C6—N1—C7—C8	−2.0 (2)	C2—C1—C9—N2	−0.3 (3)
C15—N4—C7—N1	−175.07 (19)	C6—C1—C9—N2	178.26 (16)
C16—N4—C7—N1	1.9 (3)	C2—C1—C9—C8	−177.77 (16)
C15—N4—C7—C8	4.4 (3)	C6—C1—C9—C8	0.8 (2)
C16—N4—C7—C8	−178.62 (18)	N2—C9—C8—N3	−1.55 (19)
C7—N1—C6—C5	179.12 (15)	C1—C9—C8—N3	176.52 (15)
C7—N1—C6—C1	−2.1 (3)	N2—C9—C8—C7	177.37 (14)
N1—C6—C5—C4	179.43 (17)	C1—C9—C8—C7	−4.6 (2)
C1—C6—C5—C4	0.5 (3)	C10—N3—C8—C9	1.2 (2)
C6—C5—C4—C3	−0.6 (3)	C10—N3—C8—C7	−177.58 (18)
C5—C4—C3—C2	−0.1 (3)	N1—C7—C8—C9	5.2 (2)
C4—C3—C2—C1	0.8 (3)	N4—C7—C8—C9	−174.26 (16)
C3—C2—C1—C9	177.63 (17)	N1—C7—C8—N3	−176.11 (17)
C3—C2—C1—C6	−0.8 (3)	N4—C7—C8—N3	4.4 (3)
N1—C6—C1—C2	−178.65 (15)	C8—N3—C10—N2	−0.4 (2)
C5—C6—C1—C2	0.1 (2)	C9—N2—C10—N3	−0.6 (2)
N1—C6—C1—C9	2.7 (2)	C11—N2—C10—N3	176.48 (16)
C5—C6—C1—C9	−178.54 (15)	C10—N2—C11—C12	100.8 (2)
C10—N2—C9—C8	1.26 (18)	C9—N2—C11—C12	−82.9 (2)
C11—N2—C9—C8	−175.65 (16)	N2—C11—C12—C14	−67.1 (2)
C10—N2—C9—C1	−176.54 (18)	N2—C11—C12—C13	168.91 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···N3	0.96	2.16	2.918 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯N3	0.96	2.16	2.918 (3)	135