1-Isobutyl-4-meth-oxy-1H-imidazo[4,5-c]quinoline.

In the title compound, C(15)H(17)N(3)O, the 1H-imidazo[4,5-c]quinoline ring system is approximately planar, with a maximum deviation of 0.036 (1) Å. The C-N-C-C torsion angles formed between this ring system and the isobutyl unit are -99.77 (16) and 79.71 (17)°. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains along the c axis.

Related literature

For background to quinolines and their microbial activity, see: n class="Chemical">Crozat & Beutler (2004 ▶); Stringfellow & Glasgow (1972 ▶); Miller et al. (1999 ▶); Hemmi et al. (2002 ▶). For related structures, see: Loh et al. (2011 ▶).

Experimental

Crystal data

C15H17N3O

M = 255.32

Monoclinic,

a = 7.4196 (8) Å

b = 18.910 (2) Å

c = 10.4112 (14) Å

β = 110.568 (2)°

V = 1367.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 297 K

0.40 × 0.31 × 0.13 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.969, T max = 0.989

12741 measured reflections

3463 independent reflections

2386 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.127

S = 1.04

3463 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.12 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 datablock(s) global, I. DOI: 10.1107/S1600536811031801/wn2444sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031801/wn2444Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031801/wn2444Isup3.cml

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

C15H17N3O	F(000) = 544
Mr = 255.32	Dx = 1.240 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3364 reflections
a = 7.4196 (8) Å	θ = 2.9–28.4°
b = 18.910 (2) Å	µ = 0.08 mm−1
c = 10.4112 (14) Å	T = 297 K
β = 110.568 (2)°	Plate, colourless
V = 1367.6 (3) Å3	0.40 × 0.31 × 0.13 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	3463 independent reflections
Radiation source: fine-focus sealed tube	2386 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 28.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→9
Tmin = 0.969, Tmax = 0.989	k = −25→25
12741 measured reflections	l = −13→10

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.131P] where P = (Fo2 + 2Fc2)/3
3463 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.12 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
O1	0.48715 (15)	0.63510 (5)	0.85500 (9)	0.0586 (3)
N1	0.37002 (15)	0.53191 (5)	0.73822 (10)	0.0447 (3)
N2	0.44565 (18)	0.70399 (5)	0.59706 (12)	0.0563 (3)
N3	0.33493 (16)	0.64771 (5)	0.39424 (11)	0.0486 (3)
C1	0.29597 (16)	0.49624 (6)	0.61429 (12)	0.0400 (3)
C2	0.24489 (19)	0.42505 (6)	0.61944 (13)	0.0483 (3)
H2A	0.2608	0.4045	0.7039	0.058*
C3	0.1725 (2)	0.38552 (7)	0.50312 (15)	0.0549 (3)
H3A	0.1400	0.3384	0.5089	0.066*
C4	0.1472 (2)	0.41521 (7)	0.37579 (14)	0.0563 (4)
H4A	0.0976	0.3879	0.2968	0.068*
C5	0.19492 (19)	0.48452 (7)	0.36623 (13)	0.0491 (3)
H5A	0.1776	0.5039	0.2806	0.059*
C6	0.26991 (16)	0.52691 (6)	0.48450 (12)	0.0397 (3)
C7	0.32629 (17)	0.59928 (6)	0.49100 (12)	0.0407 (3)
C8	0.39572 (18)	0.63518 (6)	0.61455 (13)	0.0445 (3)
C9	0.41477 (18)	0.59803 (6)	0.73647 (12)	0.0441 (3)
C10	0.4073 (2)	0.70816 (7)	0.46497 (16)	0.0587 (4)
H10A	0.4276	0.7491	0.4225	0.070*
C11	0.2801 (2)	0.64045 (8)	0.24607 (13)	0.0545 (3)
H11A	0.3224	0.5946	0.2258	0.065*
H11B	0.3465	0.6763	0.2129	0.065*
C12	0.0645 (2)	0.64739 (9)	0.16888 (15)	0.0639 (4)
H12A	−0.0010	0.6097	0.2001	0.077*
C13	−0.0102 (3)	0.71824 (10)	0.1988 (2)	0.0988 (7)
H13A	−0.1452	0.7221	0.1466	0.148*
H13B	0.0578	0.7559	0.1737	0.148*
H13C	0.0098	0.7214	0.2948	0.148*
C14	0.0257 (3)	0.63667 (16)	0.01661 (19)	0.1156 (9)
H14A	−0.1083	0.6447	−0.0342	0.173*
H14B	0.0591	0.5892	0.0012	0.173*
H14C	0.1018	0.6694	−0.0132	0.173*
C15	0.5158 (3)	0.59705 (9)	0.97911 (15)	0.0718 (5)
H15A	0.5586	0.6290	1.0555	0.108*
H15B	0.6111	0.5610	0.9900	0.108*
H15C	0.3968	0.5756	0.9753	0.108*

	U11	U22	U33	U12	U13	U23
O1	0.0849 (7)	0.0443 (5)	0.0409 (5)	−0.0024 (4)	0.0151 (5)	−0.0067 (4)
N1	0.0532 (6)	0.0404 (5)	0.0403 (5)	−0.0004 (4)	0.0162 (4)	−0.0010 (4)
N2	0.0727 (8)	0.0350 (6)	0.0589 (7)	0.0006 (5)	0.0202 (6)	0.0013 (5)
N3	0.0575 (6)	0.0416 (6)	0.0460 (6)	0.0052 (5)	0.0174 (5)	0.0094 (4)
C1	0.0401 (6)	0.0382 (6)	0.0419 (6)	0.0013 (4)	0.0147 (5)	−0.0012 (5)
C2	0.0547 (7)	0.0422 (7)	0.0496 (7)	−0.0038 (5)	0.0205 (6)	0.0020 (5)
C3	0.0614 (8)	0.0403 (7)	0.0622 (9)	−0.0084 (6)	0.0209 (6)	−0.0056 (6)
C4	0.0642 (9)	0.0483 (7)	0.0514 (8)	−0.0045 (6)	0.0140 (6)	−0.0134 (6)
C5	0.0561 (7)	0.0476 (7)	0.0405 (6)	0.0040 (6)	0.0130 (5)	−0.0014 (5)
C6	0.0392 (6)	0.0380 (6)	0.0407 (6)	0.0046 (5)	0.0126 (5)	0.0005 (5)
C7	0.0434 (6)	0.0377 (6)	0.0405 (6)	0.0068 (5)	0.0140 (5)	0.0054 (5)
C8	0.0517 (7)	0.0339 (6)	0.0465 (7)	0.0051 (5)	0.0154 (5)	0.0002 (5)
C9	0.0504 (7)	0.0402 (6)	0.0402 (6)	0.0041 (5)	0.0139 (5)	−0.0038 (5)
C10	0.0725 (9)	0.0381 (7)	0.0644 (9)	0.0021 (6)	0.0229 (7)	0.0091 (6)
C11	0.0586 (8)	0.0614 (8)	0.0447 (7)	0.0030 (6)	0.0196 (6)	0.0128 (6)
C12	0.0580 (8)	0.0774 (10)	0.0539 (8)	0.0034 (7)	0.0167 (7)	0.0247 (7)
C13	0.0755 (12)	0.0790 (12)	0.1277 (18)	0.0253 (9)	0.0180 (11)	0.0352 (12)
C14	0.0779 (13)	0.207 (3)	0.0512 (10)	−0.0164 (14)	0.0093 (9)	0.0234 (13)
C15	0.1055 (13)	0.0641 (10)	0.0429 (8)	−0.0088 (8)	0.0223 (8)	−0.0056 (7)

O1—C9	1.3553 (14)	C6—C7	1.4257 (16)
O1—C15	1.4281 (17)	C7—C8	1.3839 (16)
N1—C9	1.2955 (15)	C8—C9	1.4137 (17)
N1—C1	1.3870 (15)	C10—H10A	0.9300
N2—C10	1.3051 (19)	C11—C12	1.523 (2)
N2—C8	1.3825 (15)	C11—H11A	0.9700
N3—C10	1.3635 (17)	C11—H11B	0.9700
N3—C7	1.3796 (15)	C12—C14	1.522 (2)
N3—C11	1.4571 (17)	C12—C13	1.523 (3)
C1—C2	1.4046 (17)	C12—H12A	0.9800
C1—C6	1.4199 (16)	C13—H13A	0.9600
C2—C3	1.3626 (18)	C13—H13B	0.9600
C2—H2A	0.9300	C13—H13C	0.9600
C3—C4	1.3902 (19)	C14—H14A	0.9600
C3—H3A	0.9300	C14—H14B	0.9600
C4—C5	1.3705 (18)	C14—H14C	0.9600
C4—H4A	0.9300	C15—H15A	0.9600
C5—C6	1.4095 (16)	C15—H15B	0.9600
C5—H5A	0.9300	C15—H15C	0.9600
C9—O1—C15	116.66 (10)	N2—C10—N3	114.66 (12)
C9—N1—C1	118.43 (10)	N2—C10—H10A	122.7
C10—N2—C8	103.07 (11)	N3—C10—H10A	122.7
C10—N3—C7	105.82 (11)	N3—C11—C12	113.66 (11)
C10—N3—C11	124.15 (11)	N3—C11—H11A	108.8
C7—N3—C11	130.03 (11)	C12—C11—H11A	108.8
N1—C1—C2	117.04 (11)	N3—C11—H11B	108.8
N1—C1—C6	124.31 (11)	C12—C11—H11B	108.8
C2—C1—C6	118.65 (11)	H11A—C11—H11B	107.7
C3—C2—C1	121.28 (12)	C14—C12—C11	108.51 (14)
C3—C2—H2A	119.4	C14—C12—C13	112.37 (17)
C1—C2—H2A	119.4	C11—C12—C13	110.99 (14)
C2—C3—C4	120.33 (12)	C14—C12—H12A	108.3
C2—C3—H3A	119.8	C11—C12—H12A	108.3
C4—C3—H3A	119.8	C13—C12—H12A	108.3
C5—C4—C3	120.24 (12)	C12—C13—H13A	109.5
C5—C4—H4A	119.9	C12—C13—H13B	109.5
C3—C4—H4A	119.9	H13A—C13—H13B	109.5
C4—C5—C6	120.88 (12)	C12—C13—H13C	109.5
C4—C5—H5A	119.6	H13A—C13—H13C	109.5
C6—C5—H5A	119.6	H13B—C13—H13C	109.5
C5—C6—C1	118.63 (11)	C12—C14—H14A	109.5
C5—C6—C7	127.34 (11)	C12—C14—H14B	109.5
C1—C6—C7	114.03 (10)	H14A—C14—H14B	109.5
N3—C7—C8	104.80 (10)	C12—C14—H14C	109.5
N3—C7—C6	133.69 (11)	H14A—C14—H14C	109.5
C8—C7—C6	121.49 (11)	H14B—C14—H14C	109.5
N2—C8—C7	111.65 (11)	O1—C15—H15A	109.5
N2—C8—C9	129.72 (11)	O1—C15—H15B	109.5
C7—C8—C9	118.55 (11)	H15A—C15—H15B	109.5
N1—C9—O1	120.52 (11)	O1—C15—H15C	109.5
N1—C9—C8	123.15 (11)	H15A—C15—H15C	109.5
O1—C9—C8	116.31 (11)	H15B—C15—H15C	109.5
C9—N1—C1—C2	−178.62 (11)	C10—N2—C8—C7	−0.46 (15)
C9—N1—C1—C6	1.65 (18)	C10—N2—C8—C9	176.13 (14)
N1—C1—C2—C3	−179.42 (12)	N3—C7—C8—N2	0.34 (14)
C6—C1—C2—C3	0.32 (18)	C6—C7—C8—N2	178.58 (11)
C1—C2—C3—C4	−0.2 (2)	N3—C7—C8—C9	−176.68 (11)
C2—C3—C4—C5	0.1 (2)	C6—C7—C8—C9	1.57 (18)
C3—C4—C5—C6	−0.1 (2)	C1—N1—C9—O1	179.84 (11)
C4—C5—C6—C1	0.29 (19)	C1—N1—C9—C8	−1.44 (18)
C4—C5—C6—C7	179.85 (12)	C15—O1—C9—N1	1.81 (19)
N1—C1—C6—C5	179.35 (11)	C15—O1—C9—C8	−177.00 (13)
C2—C1—C6—C5	−0.37 (17)	N2—C8—C9—N1	−176.51 (13)
N1—C1—C6—C7	−0.27 (16)	C7—C8—C9—N1	−0.11 (19)
C2—C1—C6—C7	−179.99 (11)	N2—C8—C9—O1	2.3 (2)
C10—N3—C7—C8	−0.08 (14)	C7—C8—C9—O1	178.66 (11)
C11—N3—C7—C8	−179.63 (12)	C8—N2—C10—N3	0.41 (16)
C10—N3—C7—C6	−178.01 (13)	C7—N3—C10—N2	−0.22 (17)
C11—N3—C7—C6	2.4 (2)	C11—N3—C10—N2	179.36 (12)
C5—C6—C7—N3	−3.3 (2)	C10—N3—C11—C12	−99.77 (16)
C1—C6—C7—N3	176.32 (12)	C7—N3—C11—C12	79.71 (17)
C5—C6—C7—C8	179.09 (12)	N3—C11—C12—C14	−178.33 (15)
C1—C6—C7—C8	−1.33 (16)	N3—C11—C12—C13	57.73 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1i	0.93	2.39	3.3052 (16)	169.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1i	0.93	2.39	3.3052 (16)	169

Symmetry code: (i) .