7-Meth-oxy-2-phenyl-quinoline-3-carbaldehyde.

In the title mol-ecule, C17H13NO2, the phenyl ring is inclined to the quinoline ring system by 43.53 (4)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming double-stranded chains propagating along [011]. These chains are linked via π-π inter-actions involving inversion-related quinoline rings; the shortest centroid-centroid distance is 3.6596 (17) Å.

Related literature

For the synthesis and applications of similar structures, see: Montalban (2011 ▶); Wang et al. (2011 ▶); Nilsson et al. (2008 ▶); Elliott et al. (2006 ▶); Metallidis et al. (2007 ▶); Kaila et al. (2007 ▶). For related structures, see: Abdel-Wahab et al. (2012 ▶); Benzerka et al. (2011 ▶, 2012 ▶, 2013 ▶). For our previously work on the imidazol unit, see: Bouraiou et al. (2011 ▶); Hayour et al. (2011 ▶); Benzerka et al. (2012 ▶).

Experimental

Crystal data

C17H13NO2

M = 263.28

Triclinic,

a = 7.332 (3) Å

b = 7.582 (2) Å

c = 12.487 (4) Å

α = 73.424 (12)°

β = 85.877 (12)°

γ = 83.029 (11)°

V = 659.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.12 × 0.03 × 0.02 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.889, T max = 0.993

5538 measured reflections

3001 independent reflections

2344 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.138

S = 1.06

3001 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012 ▶) and CRYSCAL (T. Roisnel, local program).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001457/hg5376sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001457/hg5376Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001457/hg5376Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H13NO2	Z = 2
Mr = 263.28	F(000) = 276
Triclinic, P1	Dx = 1.325 Mg m−3
a = 7.332 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.582 (2) Å	Cell parameters from 1596 reflections
c = 12.487 (4) Å	θ = 2.9–27.7°
α = 73.424 (12)°	µ = 0.09 mm−1
β = 85.877 (12)°	T = 150 K
γ = 83.029 (11)°	Stick, yellow
V = 659.9 (4) Å3	0.12 × 0.03 × 0.02 mm

Bruker APEXII diffractometer	2344 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
CCD rotation images, thin slices scans	θmax = 27.7°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→9
Tmin = 0.889, Tmax = 0.993	k = −9→9
5538 measured reflections	l = −15→16
3001 independent reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.064P)2 + 0.0518P] where P = (Fo2 + 2Fc2)/3
3001 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.24 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
C17	0.5020 (2)	−0.08593 (18)	0.69768 (12)	0.0260 (3)
H17A	0.4055	−0.1161	0.6575	0.039*
H17B	0.5425	−0.1947	0.7585	0.039*
H17C	0.6065	−0.0489	0.6459	0.039*
C1	0.21611 (18)	0.61093 (18)	0.31036 (11)	0.0201 (3)
C2	0.13397 (18)	0.75805 (18)	0.35386 (11)	0.0204 (3)
C3	0.13446 (18)	0.73428 (18)	0.46777 (12)	0.0204 (3)
H3	0.0814	0.831	0.4983	0.025*
C4	0.21293 (17)	0.56801 (17)	0.53832 (11)	0.0187 (3)
C5	0.21827 (18)	0.53151 (18)	0.65648 (11)	0.0208 (3)
H5	0.1691	0.6246	0.691	0.025*
C6	0.29264 (19)	0.36550 (19)	0.72048 (11)	0.0221 (3)
H6	0.2969	0.3434	0.7991	0.026*
C7	0.36406 (18)	0.22478 (18)	0.66966 (11)	0.0202 (3)
C8	0.36215 (18)	0.25374 (18)	0.55626 (11)	0.0203 (3)
H8	0.4115	0.1585	0.5236	0.024*
C9	0.28617 (17)	0.42649 (17)	0.48809 (11)	0.0184 (3)
C10	0.03347 (19)	0.92782 (18)	0.28371 (12)	0.0249 (3)
H10	0.0004	0.9279	0.2115	0.03*
C11	0.23061 (18)	0.62767 (19)	0.18804 (11)	0.0222 (3)
C12	0.19420 (19)	0.4795 (2)	0.15046 (12)	0.0262 (3)
H12	0.1563	0.3708	0.2025	0.031*
C13	0.2129 (2)	0.4898 (2)	0.03792 (13)	0.0346 (4)
H13	0.1891	0.3876	0.0133	0.042*
C14	0.2660 (2)	0.6478 (3)	−0.03901 (13)	0.0426 (4)
H14	0.2765	0.6549	−0.1164	0.051*
C15	0.3037 (2)	0.7956 (2)	−0.00300 (13)	0.0399 (4)
H15	0.3419	0.9035	−0.0556	0.048*
C16	0.2860 (2)	0.7864 (2)	0.10982 (12)	0.0302 (4)
H16	0.3115	0.8885	0.1341	0.036*
N1	0.28755 (15)	0.45003 (15)	0.37525 (9)	0.0202 (3)
O1	0.43121 (14)	0.06304 (12)	0.74313 (8)	0.0250 (3)
O2	−0.00907 (16)	1.06677 (13)	0.31310 (9)	0.0343 (3)

	U11	U22	U33	U12	U13	U23
C17	0.0318 (8)	0.0184 (7)	0.0253 (7)	0.0039 (6)	−0.0022 (6)	−0.0045 (6)
C1	0.0174 (6)	0.0220 (7)	0.0197 (7)	−0.0042 (5)	0.0000 (5)	−0.0032 (5)
C2	0.0184 (7)	0.0177 (7)	0.0227 (7)	−0.0025 (5)	−0.0008 (5)	−0.0016 (5)
C3	0.0195 (7)	0.0178 (6)	0.0247 (7)	−0.0012 (5)	0.0015 (5)	−0.0079 (5)
C4	0.0162 (6)	0.0188 (7)	0.0209 (7)	−0.0031 (5)	0.0004 (5)	−0.0049 (5)
C5	0.0216 (7)	0.0209 (7)	0.0216 (7)	−0.0021 (5)	0.0021 (5)	−0.0097 (5)
C6	0.0232 (7)	0.0267 (7)	0.0175 (6)	−0.0034 (6)	0.0002 (5)	−0.0079 (5)
C7	0.0203 (7)	0.0186 (7)	0.0196 (7)	−0.0014 (5)	−0.0012 (5)	−0.0023 (5)
C8	0.0213 (7)	0.0188 (7)	0.0209 (7)	−0.0001 (5)	0.0010 (5)	−0.0069 (5)
C9	0.0171 (6)	0.0194 (7)	0.0180 (6)	−0.0029 (5)	0.0006 (5)	−0.0043 (5)
C10	0.0252 (7)	0.0214 (7)	0.0254 (7)	−0.0026 (6)	−0.0005 (6)	−0.0024 (6)
C11	0.0195 (7)	0.0261 (7)	0.0183 (7)	0.0016 (5)	−0.0025 (5)	−0.0032 (5)
C12	0.0229 (7)	0.0301 (8)	0.0244 (7)	0.0013 (6)	−0.0019 (6)	−0.0071 (6)
C13	0.0330 (9)	0.0462 (10)	0.0281 (8)	−0.0018 (7)	−0.0035 (7)	−0.0164 (7)
C14	0.0440 (10)	0.0676 (12)	0.0175 (7)	−0.0103 (9)	−0.0008 (7)	−0.0124 (8)
C15	0.0427 (10)	0.0492 (10)	0.0215 (8)	−0.0109 (8)	−0.0003 (7)	0.0026 (7)
C16	0.0314 (8)	0.0330 (8)	0.0233 (7)	−0.0061 (6)	−0.0013 (6)	−0.0020 (6)
N1	0.0210 (6)	0.0207 (6)	0.0177 (6)	−0.0009 (4)	−0.0003 (4)	−0.0041 (4)
O1	0.0343 (6)	0.0196 (5)	0.0181 (5)	0.0035 (4)	−0.0033 (4)	−0.0026 (4)
O2	0.0433 (7)	0.0198 (5)	0.0365 (6)	0.0040 (5)	−0.0032 (5)	−0.0055 (5)

C17—O1	1.4312 (16)	C7—C8	1.3706 (19)
C17—H17A	0.98	C8—C9	1.4161 (19)
C17—H17B	0.98	C8—H8	0.95
C17—H17C	0.98	C9—N1	1.3683 (17)
C1—N1	1.3270 (17)	C10—O2	1.2109 (17)
C1—C2	1.4275 (19)	C10—H10	0.95
C1—C11	1.4932 (19)	C11—C12	1.3945 (19)
C2—C3	1.3821 (19)	C11—C16	1.399 (2)
C2—C10	1.4787 (19)	C12—C13	1.383 (2)
C3—C4	1.3998 (19)	C12—H12	0.95
C3—H3	0.95	C13—C14	1.383 (2)
C4—C5	1.4241 (18)	C13—H13	0.95
C4—C9	1.4243 (19)	C14—C15	1.384 (2)
C5—C6	1.3574 (19)	C14—H14	0.95
C5—H5	0.95	C15—C16	1.388 (2)
C6—C7	1.4206 (19)	C15—H15	0.95
C6—H6	0.95	C16—H16	0.95
C7—O1	1.3654 (16)
O1—C17—H17A	109.5	C7—C8—H8	120.2
O1—C17—H17B	109.5	C9—C8—H8	120.2
H17A—C17—H17B	109.5	N1—C9—C8	117.78 (12)
O1—C17—H17C	109.5	N1—C9—C4	122.68 (12)
H17A—C17—H17C	109.5	C8—C9—C4	119.54 (12)
H17B—C17—H17C	109.5	O2—C10—C2	123.68 (14)
N1—C1—C2	122.65 (12)	O2—C10—H10	118.2
N1—C1—C11	114.92 (12)	C2—C10—H10	118.2
C2—C1—C11	122.43 (12)	C12—C11—C16	118.77 (13)
C3—C2—C1	118.67 (12)	C12—C11—C1	119.50 (12)
C3—C2—C10	118.41 (12)	C16—C11—C1	121.69 (12)
C1—C2—C10	122.68 (12)	C13—C12—C11	120.42 (14)
C2—C3—C4	120.13 (12)	C13—C12—H12	119.8
C2—C3—H3	119.9	C11—C12—H12	119.8
C4—C3—H3	119.9	C12—C13—C14	120.48 (15)
C3—C4—C5	123.80 (12)	C12—C13—H13	119.8
C3—C4—C9	117.36 (12)	C14—C13—H13	119.8
C5—C4—C9	118.81 (12)	C13—C14—C15	119.81 (14)
C6—C5—C4	120.86 (12)	C13—C14—H14	120.1
C6—C5—H5	119.6	C15—C14—H14	120.1
C4—C5—H5	119.6	C14—C15—C16	120.15 (15)
C5—C6—C7	119.88 (12)	C14—C15—H15	119.9
C5—C6—H6	120.1	C16—C15—H15	119.9
C7—C6—H6	120.1	C15—C16—C11	120.36 (14)
O1—C7—C8	124.44 (12)	C15—C16—H16	119.8
O1—C7—C6	114.26 (12)	C11—C16—H16	119.8
C8—C7—C6	121.30 (12)	C1—N1—C9	118.45 (11)
C7—C8—C9	119.60 (12)	C7—O1—C17	117.17 (11)
N1—C1—C2—C3	2.3 (2)	C3—C2—C10—O2	19.2 (2)
C11—C1—C2—C3	−176.79 (12)	C1—C2—C10—O2	−166.56 (13)
N1—C1—C2—C10	−171.97 (12)	N1—C1—C11—C12	42.75 (18)
C11—C1—C2—C10	9.0 (2)	C2—C1—C11—C12	−138.12 (14)
C1—C2—C3—C4	−0.5 (2)	N1—C1—C11—C16	−135.09 (14)
C10—C2—C3—C4	173.94 (12)	C2—C1—C11—C16	44.04 (19)
C2—C3—C4—C5	−179.58 (12)	C16—C11—C12—C13	0.1 (2)
C2—C3—C4—C9	−1.5 (2)	C1—C11—C12—C13	−177.80 (13)
C3—C4—C5—C6	178.42 (12)	C11—C12—C13—C14	−0.7 (2)
C9—C4—C5—C6	0.4 (2)	C12—C13—C14—C15	1.1 (3)
C4—C5—C6—C7	−0.9 (2)	C13—C14—C15—C16	−0.9 (3)
C5—C6—C7—O1	−178.60 (12)	C14—C15—C16—C11	0.3 (2)
C5—C6—C7—C8	1.0 (2)	C12—C11—C16—C15	0.1 (2)
O1—C7—C8—C9	178.96 (12)	C1—C11—C16—C15	177.95 (14)
C6—C7—C8—C9	−0.6 (2)	C2—C1—N1—C9	−1.7 (2)
C7—C8—C9—N1	179.76 (11)	C11—C1—N1—C9	177.47 (11)
C7—C8—C9—C4	0.1 (2)	C8—C9—N1—C1	179.72 (12)
C3—C4—C9—N1	2.2 (2)	C4—C9—N1—C1	−0.62 (19)
C5—C4—C9—N1	−179.64 (11)	C8—C7—O1—C17	−0.8 (2)
C3—C4—C9—C8	−178.14 (11)	C6—C7—O1—C17	178.80 (11)
C5—C4—C9—C8	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.48	3.349 (2)	153
C15—H15···O1ii	0.95	2.54	3.377 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.95	2.48	3.349 (2)	153
C15—H15⋯O1ii	0.95	2.54	3.377 (2)	148

Symmetry codes: (i) ; (ii) .