2-(4-Methyl-phen-yl)quinoline-4-carb-oxy-lic acid.

In the title compound, C(17)H(13)NO(2), the dihedral angle between the plane of the carb-oxy group and the quinoline mean plane is 45.05 (13)°, and that between the toluene ring mean plane and the quinoline mean plane is 25.29 (7)°. In the crystal, molecules are linked via O-H⋯.N hydrogen bonds, forming chains propagating along the b-axis direction. These chain are linked via C-H⋯O interactions, forming two-dimensional networks lying parallel to the ab plane.

Related literature

For the importance of the quinoline carb­oxy­lic acid analogues in the synthesis of various compounds with pharmacological properties, see: Deady et al. (1999 ▶, 2011 ▶); Kalluraya & Sreenivasa (1998 ▶); Tseng et al. (2008 ▶); Kravchenko et al. (2005 ▶). The structure of the related compound 2-phenyl­quinoline-4-carboxlic acid is described by Blackburn et al. (1996 ▶). For a description of puckering analysis, see: Cremer & Pople (1975 ▶). For synthetic preparation, see: Pfitzinger (1886 ▶).

Experimental

Crystal data

C17H13NO2

M = 263.28

Monoclinic,

a = 4.1001 (6) Å

b = 15.3464 (11) Å

c = 20.3037 (17) Å

β = 90.859 (9)°

V = 1277.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 291 K

0.70 × 0.08 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 ▶), based on expressions derived from Clark & Reid (1995 ▶)] T min = 0.992, T max = 0.999

4867 measured reflections

2238 independent reflections

1747 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.126

S = 1.04

2238 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203797X/go2066sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203797X/go2066Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203797X/go2066Isup3.cml

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

C17H13NO2	F(000) = 552
Mr = 263.28	Dx = 1.369 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1144 reflections
a = 4.1001 (6) Å	θ = 3.0–29.0°
b = 15.3464 (11) Å	µ = 0.09 mm−1
c = 20.3037 (17) Å	T = 291 K
β = 90.859 (9)°	Needle, clear colourless
V = 1277.4 (2) Å3	0.70 × 0.08 × 0.05 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	2238 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1747 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.0534 pixels mm-1	θmax = 25.0°, θmin = 3.3°
ω scans	h = −4→4
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]	k = −18→12
Tmin = 0.992, Tmax = 0.999	l = −24→15
4867 measured 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.213P] where P = (Fo2 + 2Fc2)/3
2238 reflections	(Δ/σ)max = 0.001
186 parameters	Δρmax = 0.20 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
O1	0.5305 (4)	0.25205 (9)	0.25810 (7)	0.0455 (4)
O2	0.7609 (5)	0.28629 (9)	0.16337 (8)	0.0636 (6)
N1	0.3552 (4)	0.57466 (9)	0.24364 (7)	0.0347 (4)
C1	−0.0757 (5)	0.69209 (12)	0.02784 (10)	0.0371 (5)
C2	−0.1462 (5)	0.71004 (12)	0.09272 (10)	0.0385 (5)
H2	−0.2786	0.7574	0.1024	0.046*
C3	−0.0247 (5)	0.65926 (12)	0.14342 (9)	0.0350 (5)
H3	−0.0740	0.6734	0.1867	0.042*
C4	0.1703 (5)	0.58721 (11)	0.13094 (9)	0.0316 (5)
C5	0.2352 (6)	0.56779 (12)	0.06552 (9)	0.0382 (5)
H5	0.3618	0.5194	0.0556	0.046*
C6	0.1145 (5)	0.61934 (13)	0.01517 (10)	0.0398 (5)
H6	0.1615	0.6051	−0.0282	0.048*
C7	0.3111 (5)	0.53556 (11)	0.18595 (9)	0.0315 (5)
C8	0.3996 (5)	0.44729 (11)	0.17666 (9)	0.0346 (5)
H8	0.3658	0.4214	0.1357	0.041*
C9	0.5335 (5)	0.39967 (11)	0.22678 (9)	0.0331 (5)
C10	0.5825 (5)	0.43954 (11)	0.28941 (9)	0.0346 (5)
C11	0.4852 (6)	0.52799 (12)	0.29539 (9)	0.0365 (5)
C12	0.5238 (7)	0.57039 (13)	0.35660 (10)	0.0529 (7)
H12	0.4589	0.6281	0.3612	0.064*
C13	0.6553 (8)	0.52727 (14)	0.40883 (11)	0.0630 (8)
H13	0.6767	0.5555	0.4492	0.076*
C14	0.7593 (7)	0.44087 (14)	0.40289 (11)	0.0585 (7)
H14	0.8527	0.4126	0.4390	0.070*
C15	0.7249 (6)	0.39806 (13)	0.34481 (10)	0.0456 (6)
H15	0.7960	0.3407	0.3414	0.055*
C16	0.6231 (5)	0.30697 (12)	0.21252 (10)	0.0360 (5)
C17	−0.2037 (7)	0.74933 (14)	−0.02685 (11)	0.0532 (6)
H17A	−0.2977	0.7137	−0.0610	0.064*
H17B	−0.0278	0.7830	−0.0444	0.064*
H17C	−0.3670	0.7878	−0.0100	0.064*
H1	0.582 (7)	0.1965 (19)	0.2521 (12)	0.072 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0703 (12)	0.0208 (7)	0.0457 (9)	0.0014 (7)	0.0106 (8)	0.0032 (6)
O2	0.1040 (16)	0.0342 (8)	0.0534 (10)	0.0071 (9)	0.0301 (10)	−0.0010 (7)
N1	0.0480 (11)	0.0239 (8)	0.0324 (9)	−0.0006 (7)	0.0012 (8)	0.0016 (7)
C1	0.0379 (13)	0.0319 (11)	0.0414 (12)	−0.0059 (9)	−0.0056 (9)	0.0034 (9)
C2	0.0379 (13)	0.0281 (10)	0.0493 (13)	0.0039 (9)	−0.0034 (10)	0.0002 (9)
C3	0.0385 (13)	0.0307 (10)	0.0360 (11)	−0.0017 (9)	0.0016 (9)	−0.0031 (8)
C4	0.0364 (12)	0.0229 (9)	0.0356 (11)	−0.0058 (8)	0.0009 (9)	−0.0002 (8)
C5	0.0476 (14)	0.0283 (10)	0.0388 (12)	0.0018 (9)	0.0017 (10)	−0.0030 (8)
C6	0.0489 (14)	0.0389 (11)	0.0315 (11)	−0.0006 (10)	0.0002 (9)	0.0002 (9)
C7	0.0371 (12)	0.0237 (9)	0.0338 (11)	−0.0038 (8)	0.0043 (9)	0.0013 (8)
C8	0.0467 (13)	0.0237 (10)	0.0332 (11)	−0.0016 (9)	0.0003 (9)	−0.0018 (8)
C9	0.0396 (13)	0.0227 (9)	0.0369 (11)	−0.0029 (8)	0.0030 (9)	0.0010 (8)
C10	0.0440 (13)	0.0225 (9)	0.0371 (11)	−0.0047 (9)	0.0003 (9)	0.0021 (8)
C11	0.0520 (14)	0.0238 (10)	0.0338 (11)	−0.0029 (9)	−0.0004 (9)	0.0029 (8)
C12	0.090 (2)	0.0286 (11)	0.0396 (13)	0.0023 (12)	−0.0062 (12)	−0.0028 (9)
C13	0.110 (2)	0.0386 (13)	0.0395 (13)	−0.0017 (14)	−0.0164 (13)	−0.0051 (10)
C14	0.092 (2)	0.0380 (12)	0.0446 (14)	0.0000 (13)	−0.0220 (13)	0.0045 (10)
C15	0.0641 (16)	0.0280 (10)	0.0444 (13)	0.0025 (10)	−0.0095 (11)	0.0026 (9)
C16	0.0462 (14)	0.0246 (10)	0.0373 (11)	−0.0013 (9)	0.0015 (10)	0.0011 (8)
C17	0.0620 (17)	0.0482 (13)	0.0490 (13)	0.0059 (12)	−0.0083 (12)	0.0107 (10)

O1—C16	1.312 (2)	C8—C9	1.362 (3)
O1—H1	0.89 (3)	C8—H8	0.9300
O2—C16	1.197 (2)	C9—C10	1.423 (3)
N1—C7	1.326 (2)	C9—C16	1.499 (3)
N1—C11	1.372 (2)	C10—C15	1.411 (3)
C1—C2	1.381 (3)	C10—C11	1.421 (3)
C1—C6	1.388 (3)	C11—C12	1.410 (3)
C1—C17	1.504 (3)	C12—C13	1.355 (3)
C2—C3	1.378 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.399 (3)
C3—C4	1.390 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.355 (3)
C4—C5	1.391 (3)	C14—H14	0.9300
C4—C7	1.480 (3)	C15—H15	0.9300
C5—C6	1.379 (3)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—C8	1.416 (3)
C16—O1—H1	116.7 (16)	C10—C9—C16	123.30 (18)
C7—N1—C11	119.10 (15)	C15—C10—C11	118.45 (17)
C2—C1—C6	117.62 (18)	C15—C10—C9	124.72 (17)
C2—C1—C17	120.81 (19)	C11—C10—C9	116.82 (17)
C6—C1—C17	121.57 (19)	N1—C11—C12	118.12 (17)
C3—C2—C1	121.42 (18)	N1—C11—C10	122.65 (17)
C3—C2—H2	119.3	C12—C11—C10	119.23 (18)
C1—C2—H2	119.3	C13—C12—C11	120.2 (2)
C2—C3—C4	121.07 (18)	C13—C12—H12	119.9
C2—C3—H3	119.5	C11—C12—H12	119.9
C4—C3—H3	119.5	C12—C13—C14	120.9 (2)
C3—C4—C5	117.60 (18)	C12—C13—H13	119.5
C3—C4—C7	120.50 (16)	C14—C13—H13	119.5
C5—C4—C7	121.87 (17)	C15—C14—C13	120.5 (2)
C6—C5—C4	120.90 (19)	C15—C14—H14	119.8
C6—C5—H5	119.6	C13—C14—H14	119.8
C4—C5—H5	119.6	C14—C15—C10	120.7 (2)
C5—C6—C1	121.37 (18)	C14—C15—H15	119.6
C5—C6—H6	119.3	C10—C15—H15	119.6
C1—C6—H6	119.3	O2—C16—O1	124.26 (18)
N1—C7—C8	121.25 (18)	O2—C16—C9	122.20 (17)
N1—C7—C4	118.09 (16)	O1—C16—C9	113.53 (17)
C8—C7—C4	120.65 (17)	C1—C17—H17A	109.5
C9—C8—C7	121.01 (18)	C1—C17—H17B	109.5
C9—C8—H8	119.5	H17A—C17—H17B	109.5
C7—C8—H8	119.5	C1—C17—H17C	109.5
C8—C9—C10	119.15 (16)	H17A—C17—H17C	109.5
C8—C9—C16	117.55 (17)	H17B—C17—H17C	109.5
C6—C1—C2—C3	1.9 (3)	C16—C9—C10—C15	1.2 (3)
C17—C1—C2—C3	−178.5 (2)	C8—C9—C10—C11	0.2 (3)
C1—C2—C3—C4	−0.9 (3)	C16—C9—C10—C11	−179.99 (19)
C2—C3—C4—C5	−0.6 (3)	C7—N1—C11—C12	−178.7 (2)
C2—C3—C4—C7	177.28 (18)	C7—N1—C11—C10	1.6 (3)
C3—C4—C5—C6	1.1 (3)	C15—C10—C11—N1	177.7 (2)
C7—C4—C5—C6	−176.78 (19)	C9—C10—C11—N1	−1.2 (3)
C4—C5—C6—C1	−0.1 (3)	C15—C10—C11—C12	−2.0 (3)
C2—C1—C6—C5	−1.4 (3)	C9—C10—C11—C12	179.1 (2)
C17—C1—C6—C5	179.0 (2)	N1—C11—C12—C13	−179.1 (2)
C11—N1—C7—C8	−0.9 (3)	C10—C11—C12—C13	0.6 (4)
C11—N1—C7—C4	179.92 (17)	C11—C12—C13—C14	1.0 (4)
C3—C4—C7—N1	−25.0 (3)	C12—C13—C14—C15	−1.2 (4)
C5—C4—C7—N1	152.79 (19)	C13—C14—C15—C10	−0.3 (4)
C3—C4—C7—C8	155.78 (19)	C11—C10—C15—C14	1.9 (4)
C5—C4—C7—C8	−26.4 (3)	C9—C10—C15—C14	−179.3 (2)
N1—C7—C8—C9	−0.1 (3)	C8—C9—C16—O2	44.3 (3)
C4—C7—C8—C9	179.09 (18)	C10—C9—C16—O2	−135.5 (2)
C7—C8—C9—C10	0.4 (3)	C8—C9—C16—O1	−134.5 (2)
C7—C8—C9—C16	−179.40 (18)	C10—C9—C16—O1	45.7 (3)
C8—C9—C10—C15	−178.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.89 (3)	1.89 (3)	2.763 (2)	168 (2)
C3—H3···O1ii	0.93	2.51	3.233 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.89 (3)	1.89 (3)	2.763 (2)	168 (2)
C3—H3⋯O1ii	0.93	2.51	3.233 (2)	135

Symmetry codes: (i) ; (ii) .