2,5-Di-methyl-phenyl quinoline-2-carboxy-l-ate.

In the title compound, C18H15NO2, the dihedral angle between the mean planes of the quinoline ring system and the phenyl ring is 78.8 (1)°. The mean plane of the carboxyl-ate group is twisted from the mean planes of the quinoline ring system and phenyl ring by 1.5 (9) and 77.6 (4)°, respectively. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, generating C(8) chains along [001]. Weak π-π stacking inter-actions are also observed [centroid-centroid separation = 3.6238 (12) Å].

Related literature

For related structures and background to quinoline derivatives, see: Fazal et al. (2014 ▶); Jasinski et al. (2010 ▶).

Experimental

Crystal data

C18H15NO2

M = 277.31

Orthorhombic,

a = 8.2261 (3) Å

b = 11.6007 (5) Å

c = 14.5738 (5) Å

V = 1390.76 (9) Å3

Z = 4

Cu Kα radiation

μ = 0.69 mm−1

T = 173 K

0.46 × 0.34 × 0.18 mm

Data collection

Agilent Gemini EOS diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.711, T max = 1.000

8332 measured reflections

2721 independent reflections

2585 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.101

S = 1.05

2721 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack parameter determined using 1049 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶)

Absolute structure parameter: −0.04 (16)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681400052X/hb7183sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400052X/hb7183Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400052X/hb7183Isup3.cml

CCDC reference:

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

C18H15NO2	Dx = 1.324 Mg m−3
Mr = 277.31	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 3982 reflections
a = 8.2261 (3) Å	θ = 3.0–72.4°
b = 11.6007 (5) Å	µ = 0.69 mm−1
c = 14.5738 (5) Å	T = 173 K
V = 1390.76 (9) Å3	Irregular, colourless
Z = 4	0.46 × 0.34 × 0.18 mm
F(000) = 584

Agilent Gemini EOS diffractometer	2721 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2585 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.031
ω scans	θmax = 72.6°, θmin = 4.9°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −6→10
Tmin = 0.711, Tmax = 1.000	k = −14→13
8332 measured reflections	l = −17→17

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0609P)2 + 0.1748P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.035	(Δ/σ)max = 0.008
wR(F2) = 0.101	Δρmax = 0.18 e Å−3
S = 1.05	Δρmin = −0.16 e Å−3
2721 reflections	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
193 parameters	Extinction coefficient: 0.0027 (7)
0 restraints	Absolute structure: Flack parameter determined using 1049 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (16)
Hydrogen site location: inferred from neighbouring sites

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	0.4090 (2)	0.00776 (14)	0.45505 (11)	0.0439 (4)
O2	0.5803 (2)	0.13777 (12)	0.39481 (9)	0.0330 (4)
N1	0.3984 (2)	0.13265 (14)	0.61466 (11)	0.0259 (4)
C1	0.4863 (2)	0.09441 (16)	0.46254 (13)	0.0274 (4)
C2	0.4902 (2)	0.16990 (15)	0.54669 (12)	0.0248 (4)
C3	0.5847 (2)	0.27162 (16)	0.54988 (13)	0.0276 (4)
H3	0.6468	0.2956	0.4984	0.033*
C4	0.5840 (3)	0.33438 (17)	0.62920 (14)	0.0292 (4)
H4	0.6464	0.4031	0.6334	0.035*
C5	0.4907 (3)	0.29728 (16)	0.70485 (13)	0.0265 (4)
C6	0.4872 (3)	0.35546 (17)	0.79056 (14)	0.0321 (4)
H6	0.5502	0.4232	0.7992	0.038*
C7	0.3934 (3)	0.31404 (19)	0.86066 (14)	0.0349 (5)
H7	0.3927	0.3529	0.9180	0.042*
C8	0.2979 (3)	0.21456 (19)	0.84884 (14)	0.0334 (5)
H8	0.2323	0.1877	0.8981	0.040*
C9	0.2982 (3)	0.15600 (17)	0.76741 (14)	0.0296 (4)
H9	0.2325	0.0893	0.7601	0.035*
C10	0.3968 (2)	0.19518 (16)	0.69387 (13)	0.0252 (4)
C11	0.5828 (2)	0.07494 (17)	0.31151 (12)	0.0271 (4)
C12	0.6794 (2)	−0.02221 (17)	0.30398 (14)	0.0286 (4)
C13	0.6803 (3)	−0.07618 (18)	0.21885 (14)	0.0318 (4)
H13	0.7445	−0.1435	0.2107	0.038*
C14	0.5903 (3)	−0.03456 (18)	0.14550 (14)	0.0326 (5)
H14	0.5932	−0.0740	0.0884	0.039*
C15	0.4960 (2)	0.06388 (18)	0.15446 (13)	0.0313 (4)
C16	0.4932 (3)	0.11850 (17)	0.23933 (14)	0.0294 (4)
H16	0.4294	0.1860	0.2477	0.035*
C17	0.4019 (3)	0.1117 (2)	0.07440 (16)	0.0452 (6)
H17A	0.3427	0.1809	0.0938	0.068*
H17B	0.3245	0.0537	0.0525	0.068*
H17C	0.4772	0.1318	0.0248	0.068*
C18	0.7792 (3)	−0.0662 (2)	0.38316 (16)	0.0400 (5)
H18A	0.8297	−0.0011	0.4151	0.060*
H18B	0.8640	−0.1180	0.3601	0.060*
H18C	0.7088	−0.1083	0.4258	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0543 (10)	0.0445 (9)	0.0330 (8)	−0.0212 (8)	0.0128 (8)	−0.0122 (7)
O2	0.0444 (8)	0.0311 (7)	0.0235 (7)	−0.0073 (6)	0.0076 (6)	−0.0061 (5)
N1	0.0281 (8)	0.0265 (8)	0.0232 (8)	0.0012 (7)	0.0003 (7)	−0.0005 (6)
C1	0.0283 (9)	0.0294 (9)	0.0246 (9)	−0.0001 (8)	0.0006 (8)	−0.0011 (7)
C2	0.0270 (8)	0.0262 (9)	0.0211 (8)	0.0032 (8)	−0.0015 (8)	−0.0008 (7)
C3	0.0305 (9)	0.0273 (9)	0.0251 (9)	0.0009 (8)	0.0008 (8)	0.0019 (7)
C4	0.0327 (9)	0.0237 (9)	0.0311 (10)	−0.0010 (8)	−0.0015 (8)	−0.0002 (8)
C5	0.0308 (9)	0.0238 (9)	0.0248 (9)	0.0061 (8)	−0.0032 (8)	−0.0015 (7)
C6	0.0415 (11)	0.0251 (9)	0.0296 (10)	0.0033 (9)	−0.0039 (9)	−0.0041 (7)
C7	0.0453 (11)	0.0359 (11)	0.0234 (9)	0.0113 (10)	−0.0012 (9)	−0.0056 (8)
C8	0.0372 (10)	0.0397 (11)	0.0232 (9)	0.0093 (9)	0.0029 (9)	0.0028 (8)
C9	0.0302 (9)	0.0321 (10)	0.0264 (10)	0.0025 (8)	−0.0001 (8)	0.0021 (8)
C10	0.0269 (9)	0.0255 (9)	0.0234 (8)	0.0052 (8)	−0.0015 (7)	0.0004 (7)
C11	0.0336 (10)	0.0254 (9)	0.0222 (8)	−0.0067 (8)	0.0048 (8)	−0.0033 (7)
C12	0.0289 (9)	0.0281 (9)	0.0288 (10)	−0.0035 (8)	0.0038 (8)	0.0017 (8)
C13	0.0338 (10)	0.0272 (9)	0.0344 (10)	−0.0004 (9)	0.0087 (9)	−0.0026 (8)
C14	0.0377 (10)	0.0345 (11)	0.0256 (9)	−0.0093 (9)	0.0046 (9)	−0.0091 (8)
C15	0.0300 (9)	0.0375 (10)	0.0263 (9)	−0.0080 (9)	0.0015 (9)	0.0012 (8)
C16	0.0316 (9)	0.0271 (9)	0.0296 (10)	0.0012 (9)	0.0056 (8)	0.0005 (7)
C17	0.0443 (12)	0.0608 (15)	0.0306 (11)	−0.0007 (12)	−0.0047 (10)	0.0035 (10)
C18	0.0411 (12)	0.0450 (12)	0.0338 (11)	0.0028 (10)	0.0004 (10)	0.0049 (10)

O1—C1	1.194 (2)	C9—H9	0.9500
O2—C1	1.351 (2)	C9—C10	1.419 (3)
O2—C11	1.416 (2)	C11—C12	1.383 (3)
N1—C2	1.319 (2)	C11—C16	1.380 (3)
N1—C10	1.363 (2)	C12—C13	1.390 (3)
C1—C2	1.507 (2)	C12—C18	1.505 (3)
C2—C3	1.414 (3)	C13—H13	0.9500
C3—H3	0.9500	C13—C14	1.387 (3)
C3—C4	1.366 (3)	C14—H14	0.9500
C4—H4	0.9500	C14—C15	1.387 (3)
C4—C5	1.411 (3)	C15—C16	1.390 (3)
C5—C6	1.420 (2)	C15—C17	1.507 (3)
C5—C10	1.423 (3)	C16—H16	0.9500
C6—H6	0.9500	C17—H17A	0.9800
C6—C7	1.368 (3)	C17—H17B	0.9800
C7—H7	0.9500	C17—H17C	0.9800
C7—C8	1.407 (3)	C18—H18A	0.9800
C8—H8	0.9500	C18—H18B	0.9800
C8—C9	1.367 (3)	C18—H18C	0.9800
C1—O2—C11	116.31 (15)	C9—C10—C5	119.47 (17)
C2—N1—C10	117.84 (16)	C12—C11—O2	119.72 (17)
O1—C1—O2	123.44 (18)	C16—C11—O2	117.19 (17)
O1—C1—C2	125.08 (18)	C16—C11—C12	123.00 (17)
O2—C1—C2	111.47 (16)	C11—C12—C13	116.18 (18)
N1—C2—C1	114.13 (16)	C11—C12—C18	121.93 (18)
N1—C2—C3	124.32 (17)	C13—C12—C18	121.89 (19)
C3—C2—C1	121.55 (17)	C12—C13—H13	119.1
C2—C3—H3	121.0	C14—C13—C12	121.88 (19)
C4—C3—C2	118.05 (18)	C14—C13—H13	119.1
C4—C3—H3	121.0	C13—C14—H14	119.6
C3—C4—H4	120.0	C15—C14—C13	120.84 (18)
C3—C4—C5	120.07 (18)	C15—C14—H14	119.6
C5—C4—H4	120.0	C14—C15—C16	117.95 (19)
C4—C5—C6	123.59 (18)	C14—C15—C17	121.20 (19)
C4—C5—C10	117.47 (16)	C16—C15—C17	120.8 (2)
C6—C5—C10	118.93 (17)	C11—C16—C15	120.15 (19)
C5—C6—H6	120.0	C11—C16—H16	119.9
C7—C6—C5	120.08 (19)	C15—C16—H16	119.9
C7—C6—H6	120.0	C15—C17—H17A	109.5
C6—C7—H7	119.6	C15—C17—H17B	109.5
C6—C7—C8	120.80 (18)	C15—C17—H17C	109.5
C8—C7—H7	119.6	H17A—C17—H17B	109.5
C7—C8—H8	119.6	H17A—C17—H17C	109.5
C9—C8—C7	120.9 (2)	H17B—C17—H17C	109.5
C9—C8—H8	119.6	C12—C18—H18A	109.5
C8—C9—H9	120.1	C12—C18—H18B	109.5
C8—C9—C10	119.82 (19)	C12—C18—H18C	109.5
C10—C9—H9	120.1	H18A—C18—H18B	109.5
N1—C10—C5	122.21 (17)	H18A—C18—H18C	109.5
N1—C10—C9	118.32 (17)	H18B—C18—H18C	109.5
O1—C1—C2—N1	−0.1 (3)	C6—C5—C10—C9	2.1 (3)
O1—C1—C2—C3	−179.8 (2)	C6—C7—C8—C9	0.9 (3)
O2—C1—C2—N1	178.98 (16)	C7—C8—C9—C10	0.5 (3)
O2—C1—C2—C3	−0.7 (3)	C8—C9—C10—N1	177.87 (18)
O2—C11—C12—C13	−177.39 (17)	C8—C9—C10—C5	−1.9 (3)
O2—C11—C12—C18	2.0 (3)	C10—N1—C2—C1	179.07 (16)
O2—C11—C16—C15	177.19 (17)	C10—N1—C2—C3	−1.3 (3)
N1—C2—C3—C4	1.5 (3)	C10—C5—C6—C7	−0.8 (3)
C1—O2—C11—C12	−79.9 (2)	C11—O2—C1—O1	0.5 (3)
C1—O2—C11—C16	103.4 (2)	C11—O2—C1—C2	−178.63 (15)
C1—C2—C3—C4	−178.88 (17)	C11—C12—C13—C14	0.3 (3)
C2—N1—C10—C5	−0.3 (3)	C12—C11—C16—C15	0.6 (3)
C2—N1—C10—C9	179.87 (17)	C12—C13—C14—C15	0.5 (3)
C2—C3—C4—C5	−0.1 (3)	C13—C14—C15—C16	−0.8 (3)
C3—C4—C5—C6	177.96 (18)	C13—C14—C15—C17	178.1 (2)
C3—C4—C5—C10	−1.4 (3)	C14—C15—C16—C11	0.2 (3)
C4—C5—C6—C7	179.9 (2)	C16—C11—C12—C13	−0.9 (3)
C4—C5—C10—N1	1.6 (3)	C16—C11—C12—C18	178.5 (2)
C4—C5—C10—C9	−178.58 (18)	C17—C15—C16—C11	−178.65 (19)
C5—C6—C7—C8	−0.7 (3)	C18—C12—C13—C14	−179.00 (19)
C6—C5—C10—N1	−177.74 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···O1i	0.98	2.49	3.389 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17B⋯O1i	0.98	2.49	3.389 (3)	152

Symmetry code: (i) .