8-Meth-oxy-4-(4-methoxy-phen-yl)quinoline.

In the title compound, C(17)H(15)NO(2), the dihedral angle between the quinoline and benzene ring systems is 62.17 (1)°. In the crystal, zigzag chains propagating in c are linked by C-H⋯O hydrogen bonds, and weak C-H⋯π inter-actions link the chains.

Related literature

The title compound was prepared as an inter­mediate for the synthesis of aluminium(III) quinolinolate complexes, which are important for their semiconductor properties and as electron-transport layer materials in organic light-emitting devices (OLEDs) (Montes et al., 2006 ▶). For related literature, see: Dienys et al. (1977 ▶); Muscia et al. (2006 ▶); Pérez-Bolívar et al. (2006 ▶).

Experimental

Crystal data

C17H15NO2

M = 265.30

Monoclinic,

a = 9.362 (2) Å

b = 10.355 (2) Å

c = 14.276 (4) Å

β = 101.556 (6)°

V = 1355.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.45 × 0.42 × 0.40 mm

Data collection

Rigaku AFC-7S Mercury diffractometer

Absorption correction: multi-scan (ABSCOR; Jacobson, 1998 ▶) T min = 0.940, T max = 0.980

15093 measured reflections

2785 independent reflections

1868 reflections with I > 2σ(I)

R int = 0.037

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.145

S = 1.12

2785 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶)); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052623/hb5272sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052623/hb5272Isup2.hkl

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

C17H15NO2	F(000) = 560
Mr = 265.30	Dx = 1.300 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 8153 reflections
a = 9.362 (2) Å	θ = 4.4–55.8°
b = 10.355 (2) Å	µ = 0.09 mm−1
c = 14.276 (4) Å	T = 295 K
β = 101.556 (6)°	Block, light brown
V = 1355.9 (5) Å3	0.45 × 0.42 × 0.40 mm
Z = 4

Rigaku AFC-7S Mercury diffractometer	2785 independent reflections
Radiation source: Normal-focus sealed tube	1868 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω scans	θmax = 28.1°, θmin = 56.1°
Absorption correction: multi-scan (ABSCOR; Jacobson, 1998)	h = −12→12
Tmin = 0.940, Tmax = 0.980	k = −13→13
15093 measured reflections	l = −18→18

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0538P)2 + 0.3325P] where P = (Fo2 + 2Fc2)/3
2785 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.23 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	0.42442 (15)	0.09277 (15)	0.26653 (10)	0.0576 (4)
O2	−0.41766 (17)	0.34353 (16)	0.58150 (11)	0.0644 (5)
N1	0.22017 (18)	0.27365 (17)	0.23541 (12)	0.0507 (5)
C1	0.1179 (2)	0.3624 (2)	0.22134 (16)	0.0554 (6)
H1A	0.1163	0.4196	0.1709	0.066*
C2	0.0111 (2)	0.3774 (2)	0.27655 (15)	0.0522 (5)
H2A	−0.0583	0.4424	0.2618	0.063*
C3	0.0082 (2)	0.29631 (19)	0.35232 (14)	0.0427 (5)
C4	0.1152 (2)	0.19600 (18)	0.36953 (13)	0.0397 (5)
C5	0.1192 (2)	0.10133 (19)	0.44199 (14)	0.0456 (5)
H5A	0.0515	0.1042	0.4815	0.055*
C6	0.2215 (2)	0.0066 (2)	0.45375 (15)	0.0493 (5)
H6A	0.2217	−0.0556	0.5007	0.059*
C7	0.3275 (2)	0.0006 (2)	0.39636 (15)	0.0495 (5)
H7A	0.3978	−0.0641	0.4066	0.059*
C8	0.3271 (2)	0.08987 (19)	0.32555 (14)	0.0441 (5)
C9	0.2189 (2)	0.18964 (19)	0.30946 (13)	0.0414 (5)
C10	−0.1047 (2)	0.31030 (19)	0.41186 (14)	0.0447 (5)
C11	−0.2518 (2)	0.2989 (2)	0.37074 (15)	0.0504 (5)
H11A	−0.2788	0.2841	0.3053	0.060*
C12	−0.3598 (2)	0.3091 (2)	0.42425 (15)	0.0512 (5)
H12A	−0.4574	0.3001	0.3950	0.061*
C13	−0.3213 (2)	0.33263 (19)	0.52103 (16)	0.0491 (5)
C14	−0.1750 (2)	0.3464 (2)	0.56353 (16)	0.0554 (6)
H14A	−0.1487	0.3634	0.6287	0.066*
C15	−0.0685 (2)	0.3350 (2)	0.50986 (15)	0.0524 (5)
H15A	0.0289	0.3440	0.5394	0.063*
C16	0.5389 (2)	−0.0015 (2)	0.28179 (17)	0.0632 (7)
H16A	0.5999	0.0110	0.2359	0.095*
H16B	0.4973	−0.0865	0.2745	0.095*
H16C	0.5962	0.0080	0.3452	0.095*
C17	−0.5693 (2)	0.3254 (2)	0.54239 (18)	0.0653 (7)
H17A	−0.6242	0.3361	0.5919	0.098*
H17B	−0.5847	0.2401	0.5161	0.098*
H17C	−0.6007	0.3879	0.4929	0.098*

	U11	U22	U33	U12	U13	U23
O1	0.0497 (8)	0.0726 (10)	0.0547 (9)	0.0123 (7)	0.0206 (7)	0.0055 (8)
O2	0.0592 (10)	0.0763 (11)	0.0643 (10)	−0.0038 (8)	0.0281 (8)	−0.0167 (8)
N1	0.0478 (10)	0.0584 (11)	0.0476 (10)	0.0007 (9)	0.0135 (8)	0.0117 (9)
C1	0.0549 (13)	0.0598 (14)	0.0523 (13)	0.0004 (11)	0.0127 (11)	0.0194 (11)
C2	0.0478 (12)	0.0542 (13)	0.0549 (13)	0.0060 (10)	0.0113 (10)	0.0133 (10)
C3	0.0396 (10)	0.0438 (11)	0.0442 (11)	−0.0042 (9)	0.0074 (9)	0.0013 (9)
C4	0.0384 (10)	0.0414 (11)	0.0387 (10)	−0.0056 (8)	0.0067 (8)	−0.0004 (8)
C5	0.0474 (11)	0.0458 (11)	0.0455 (11)	−0.0047 (9)	0.0136 (9)	0.0041 (9)
C6	0.0557 (12)	0.0451 (11)	0.0470 (11)	−0.0009 (10)	0.0101 (10)	0.0065 (10)
C7	0.0498 (12)	0.0463 (12)	0.0521 (12)	0.0068 (9)	0.0099 (10)	0.0020 (10)
C8	0.0405 (11)	0.0498 (12)	0.0425 (11)	−0.0012 (9)	0.0095 (9)	−0.0013 (9)
C9	0.0396 (10)	0.0450 (11)	0.0394 (10)	−0.0053 (9)	0.0073 (9)	0.0018 (9)
C10	0.0454 (11)	0.0423 (11)	0.0477 (12)	0.0003 (9)	0.0125 (9)	0.0029 (9)
C11	0.0474 (12)	0.0601 (14)	0.0447 (11)	0.0037 (10)	0.0116 (10)	0.0042 (10)
C12	0.0441 (11)	0.0561 (13)	0.0543 (13)	0.0033 (10)	0.0117 (10)	0.0022 (10)
C13	0.0523 (13)	0.0434 (11)	0.0558 (13)	0.0006 (10)	0.0210 (11)	−0.0056 (10)
C14	0.0600 (14)	0.0581 (14)	0.0496 (12)	−0.0061 (11)	0.0147 (11)	−0.0129 (10)
C15	0.0481 (12)	0.0558 (13)	0.0533 (13)	−0.0051 (10)	0.0097 (10)	−0.0078 (10)
C16	0.0515 (13)	0.0772 (17)	0.0623 (14)	0.0151 (12)	0.0149 (11)	−0.0052 (13)
C17	0.0538 (14)	0.0707 (16)	0.0780 (17)	0.0002 (12)	0.0290 (12)	−0.0118 (13)

O1—C8	1.360 (2)	C7—H7A	0.9300
O1—C16	1.434 (3)	C8—C9	1.433 (3)
O2—C13	1.373 (2)	C10—C11	1.390 (3)
O2—C17	1.429 (3)	C10—C15	1.396 (3)
N1—C1	1.313 (3)	C11—C12	1.388 (3)
N1—C9	1.371 (2)	C11—H11A	0.9300
C1—C2	1.401 (3)	C12—C13	1.378 (3)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.374 (3)	C13—C14	1.390 (3)
C2—H2A	0.9300	C14—C15	1.379 (3)
C3—C4	1.430 (3)	C14—H14A	0.9300
C3—C10	1.490 (3)	C15—H15A	0.9300
C4—C9	1.419 (3)	C16—H16A	0.9600
C4—C5	1.420 (3)	C16—H16B	0.9600
C5—C6	1.358 (3)	C16—H16C	0.9600
C5—H5A	0.9300	C17—H17A	0.9600
C6—C7	1.409 (3)	C17—H17B	0.9600
C6—H6A	0.9300	C17—H17C	0.9600
C7—C8	1.369 (3)
C8—O1—C16	117.66 (17)	C11—C10—C15	117.36 (19)
C13—O2—C17	118.02 (17)	C11—C10—C3	120.48 (18)
C1—N1—C9	116.31 (17)	C15—C10—C3	122.16 (18)
N1—C1—C2	124.90 (19)	C12—C11—C10	122.1 (2)
N1—C1—H1A	117.5	C12—C11—H11A	119.0
C2—C1—H1A	117.5	C10—C11—H11A	119.0
C3—C2—C1	120.3 (2)	C13—C12—C11	119.5 (2)
C3—C2—H2A	119.9	C13—C12—H12A	120.3
C1—C2—H2A	119.9	C11—C12—H12A	120.3
C2—C3—C4	117.12 (18)	O2—C13—C12	124.90 (19)
C2—C3—C10	121.17 (18)	O2—C13—C14	115.56 (19)
C4—C3—C10	121.69 (17)	C12—C13—C14	119.5 (2)
C9—C4—C5	119.13 (17)	C15—C14—C13	120.5 (2)
C9—C4—C3	118.05 (17)	C15—C14—H14A	119.7
C5—C4—C3	122.80 (18)	C13—C14—H14A	119.7
C6—C5—C4	120.22 (19)	C14—C15—C10	121.0 (2)
C6—C5—H5A	119.9	C14—C15—H15A	119.5
C4—C5—H5A	119.9	C10—C15—H15A	119.5
C5—C6—C7	121.45 (19)	O1—C16—H16A	109.5
C5—C6—H6A	119.3	O1—C16—H16B	109.5
C7—C6—H6A	119.3	H16A—C16—H16B	109.5
C8—C7—C6	120.08 (19)	O1—C16—H16C	109.5
C8—C7—H7A	120.0	H16A—C16—H16C	109.5
C6—C7—H7A	120.0	H16B—C16—H16C	109.5
O1—C8—C7	124.69 (18)	O2—C17—H17A	109.5
O1—C8—C9	115.14 (17)	O2—C17—H17B	109.5
C7—C8—C9	120.16 (18)	H17A—C17—H17B	109.5
N1—C9—C4	123.31 (18)	O2—C17—H17C	109.5
N1—C9—C8	117.77 (17)	H17A—C17—H17C	109.5
C4—C9—C8	118.92 (17)	H17B—C17—H17C	109.5

Cg2and Cg3 are the centroids of the C4–C9 and C10–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O1i	0.96	2.55	3.322 (3)	137
C2—H2A···Cg2ii	0.93	2.81	3.622 (2)	146
C6—H6A···Cg3iii	0.93	2.80	3.592 (2)	144
C17—H17B···Cg2iv	0.96	2.78	3.580 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O1i	0.96	2.55	3.322 (3)	137
C2—H2A⋯Cg2ii	0.93	2.81	3.622 (2)	146
C6—H6A⋯Cg3iii	0.93	2.80	3.592 (2)	144
C17—H17B⋯Cg2iv	0.96	2.78	3.580 (3)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 and Cg3 are the centroids of the C4–C9 and C10–C14 rings, respectively.