4-Chloro-phenyl quinoline-2-carboxyl-ate.

In the title compound, C16H10ClNO2, the dihedral angle between the quinoline ring system and the benzene ring is 14.7 (5)°. The carboxyl-ate group is twisted from the mean planes of the quinoline ring system and the benzene ring by 17.7 (5) and 32.1 (4)°, respectively. In the crystal, inversion dimers are formed with the molecules linked by pairs of weak C-H⋯O inter-actions arising from an activated aromatic C atom adjacent to the C-Cl bond, generating R 2 (2)(14) loops.

Related literature

For related structures, see: Fazal et al. (2012 ▶); Butcher et al. (2007 ▶); Jing & Qin (2008 ▶); Jasinski et al. (2010 ▶).

Experimental

Crystal data

C16H10ClNO2

M = 283.70

Monoclinic,

a = 6.38693 (18) Å

b = 16.8893 (5) Å

c = 12.2649 (4) Å

β = 103.527 (3)°

V = 1286.33 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.63 mm−1

T = 173 K

0.34 × 0.18 × 0.12 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.611, T max = 1.000

7778 measured reflections

2502 independent reflections

2168 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 1.05

2502 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

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/S1600536813032054/hb7166sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032054/hb7166Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813032054/hb7166Isup3.cml

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

C16H10ClNO2	F(000) = 584
Mr = 283.70	Dx = 1.465 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 6.38693 (18) Å	Cell parameters from 3028 reflections
b = 16.8893 (5) Å	θ = 3.7–72.3°
c = 12.2649 (4) Å	µ = 2.63 mm−1
β = 103.527 (3)°	T = 173 K
V = 1286.33 (6) Å3	Irregular, colourless
Z = 4	0.34 × 0.18 × 0.12 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	2502 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2168 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.032
ω scans	θmax = 72.5°, θmin = 4.5°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −5→7
Tmin = 0.611, Tmax = 1.000	k = −20→20
7778 measured reflections	l = −15→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2502 reflections	Δρmax = 0.21 e Å−3
181 parameters	Δρmin = −0.25 e Å−3
0 restraints

Experimental. 1H NMR(500MHz,DMSO) δ 8.6 (1H,d, J= 8.48Hz), 8.34(1H,d, J= 8.49Hz),8.29(1H,d, J= 8.49Hz), 8.08(1H,d, J= 8.23 Hz),7.91(1H,dt, J1= 8.2Hz, J2=7, J3=1.36Hz), 7.79(1H,t, J= 7.73Hz), 7.51(2H,d, J= 8.78Hz), 7.38(2H,d, J= 8.78Hz)

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
Cl1	1.24130 (8)	0.40648 (3)	0.40342 (4)	0.04923 (18)
O1	0.61750 (19)	0.56656 (7)	−0.05303 (10)	0.0362 (3)
O2	0.57559 (18)	0.60496 (7)	0.11776 (9)	0.0291 (3)
N1	0.2144 (2)	0.68008 (8)	0.02285 (11)	0.0255 (3)
C1	0.5257 (3)	0.60419 (9)	0.00414 (13)	0.0271 (3)
C2	0.3381 (3)	0.65748 (9)	−0.04352 (13)	0.0257 (3)
C3	0.3074 (3)	0.67937 (10)	−0.15754 (13)	0.0299 (4)
H3	0.3984	0.6606	−0.2008	0.036*
C4	0.1399 (3)	0.72894 (10)	−0.20223 (13)	0.0316 (4)
H4	0.1179	0.7457	−0.2763	0.038*
C5	0.0005 (3)	0.75454 (9)	−0.13540 (13)	0.0268 (3)
C6	−0.1776 (3)	0.80535 (10)	−0.17629 (14)	0.0317 (4)
H6	−0.2050	0.8240	−0.2496	0.038*
C7	−0.3082 (3)	0.82679 (10)	−0.10810 (15)	0.0333 (4)
H7	−0.4250	0.8600	−0.1353	0.040*
C8	−0.2682 (3)	0.79909 (10)	0.00373 (14)	0.0313 (4)
H8	−0.3602	0.8138	0.0489	0.038*
C9	−0.0962 (3)	0.75108 (9)	0.04632 (13)	0.0285 (4)
H9	−0.0708	0.7337	0.1202	0.034*
C10	0.0434 (3)	0.72779 (9)	−0.02247 (12)	0.0250 (3)
C11	0.7396 (3)	0.55652 (9)	0.17935 (13)	0.0266 (3)
C12	0.9292 (3)	0.53939 (10)	0.14730 (14)	0.0312 (4)
H12	0.9532	0.5588	0.0803	0.037*
C13	1.0823 (3)	0.49268 (10)	0.21764 (15)	0.0328 (4)
H13	1.2095	0.4797	0.1973	0.039*
C14	1.0458 (3)	0.46548 (10)	0.31740 (15)	0.0314 (4)
C15	0.8591 (3)	0.48398 (10)	0.35058 (14)	0.0314 (4)
H15	0.8375	0.4659	0.4187	0.038*
C16	0.7051 (3)	0.52997 (10)	0.28040 (14)	0.0284 (3)
H16	0.5784	0.5430	0.3012	0.034*

	U11	U22	U33	U12	U13	U23
Cl1	0.0401 (3)	0.0515 (3)	0.0530 (3)	0.0174 (2)	0.0047 (2)	0.0118 (2)
O1	0.0361 (7)	0.0436 (7)	0.0297 (6)	0.0062 (5)	0.0094 (5)	−0.0075 (5)
O2	0.0313 (6)	0.0318 (6)	0.0243 (6)	0.0059 (5)	0.0068 (4)	−0.0011 (4)
N1	0.0294 (7)	0.0249 (6)	0.0221 (6)	−0.0011 (5)	0.0056 (5)	−0.0001 (5)
C1	0.0294 (8)	0.0276 (8)	0.0250 (8)	−0.0035 (6)	0.0076 (6)	−0.0032 (6)
C2	0.0282 (8)	0.0252 (8)	0.0242 (7)	−0.0038 (6)	0.0069 (6)	−0.0025 (6)
C3	0.0339 (9)	0.0343 (9)	0.0236 (8)	−0.0026 (7)	0.0110 (7)	−0.0024 (6)
C4	0.0400 (10)	0.0358 (9)	0.0192 (7)	−0.0041 (7)	0.0075 (7)	0.0021 (6)
C5	0.0305 (8)	0.0254 (8)	0.0230 (7)	−0.0055 (6)	0.0031 (6)	0.0002 (6)
C6	0.0350 (9)	0.0313 (8)	0.0262 (8)	−0.0041 (7)	0.0018 (7)	0.0045 (6)
C7	0.0307 (9)	0.0291 (8)	0.0377 (9)	0.0017 (7)	0.0033 (7)	0.0038 (7)
C8	0.0323 (9)	0.0297 (8)	0.0338 (9)	−0.0002 (7)	0.0116 (7)	−0.0007 (7)
C9	0.0334 (9)	0.0286 (8)	0.0239 (7)	−0.0005 (6)	0.0074 (6)	0.0014 (6)
C10	0.0286 (8)	0.0234 (7)	0.0224 (7)	−0.0038 (6)	0.0047 (6)	−0.0006 (6)
C11	0.0263 (8)	0.0250 (8)	0.0273 (8)	0.0001 (6)	0.0042 (6)	−0.0024 (6)
C12	0.0313 (9)	0.0342 (9)	0.0296 (8)	−0.0022 (7)	0.0104 (7)	−0.0017 (7)
C13	0.0264 (9)	0.0360 (9)	0.0370 (9)	0.0020 (7)	0.0093 (7)	−0.0053 (7)
C14	0.0281 (9)	0.0274 (8)	0.0359 (9)	0.0032 (6)	0.0020 (7)	−0.0009 (7)
C15	0.0318 (9)	0.0316 (8)	0.0305 (8)	−0.0010 (7)	0.0068 (7)	0.0020 (7)
C16	0.0249 (8)	0.0312 (8)	0.0304 (8)	0.0004 (6)	0.0093 (6)	−0.0025 (6)

Cl1—C14	1.7459 (17)	C7—H7	0.9300
O1—C1	1.1963 (19)	C7—C8	1.415 (2)
O2—C1	1.3549 (19)	C8—H8	0.9300
O2—C11	1.4025 (19)	C8—C9	1.367 (2)
N1—C2	1.317 (2)	C9—H9	0.9300
N1—C10	1.366 (2)	C9—C10	1.419 (2)
C1—C2	1.503 (2)	C11—C12	1.388 (2)
C2—C3	1.415 (2)	C11—C16	1.383 (2)
C3—H3	0.9300	C12—H12	0.9300
C3—C4	1.368 (2)	C12—C13	1.388 (2)
C4—H4	0.9300	C13—H13	0.9300
C4—C5	1.411 (2)	C13—C14	1.377 (2)
C5—C6	1.420 (2)	C14—C15	1.383 (2)
C5—C10	1.421 (2)	C15—H15	0.9300
C6—H6	0.9300	C15—C16	1.384 (2)
C6—C7	1.361 (3)	C16—H16	0.9300
C1—O2—C11	120.97 (12)	C9—C8—H8	119.6
C2—N1—C10	117.23 (13)	C8—C9—H9	120.1
O1—C1—O2	125.33 (15)	C8—C9—C10	119.85 (15)
O1—C1—C2	123.05 (15)	C10—C9—H9	120.1
O2—C1—C2	111.61 (13)	N1—C10—C5	122.51 (14)
N1—C2—C1	118.18 (14)	N1—C10—C9	118.37 (14)
N1—C2—C3	124.79 (15)	C9—C10—C5	119.12 (15)
C3—C2—C1	117.03 (14)	C12—C11—O2	124.07 (14)
C2—C3—H3	121.0	C16—C11—O2	114.59 (13)
C4—C3—C2	118.07 (15)	C16—C11—C12	121.23 (15)
C4—C3—H3	121.0	C11—C12—H12	120.8
C3—C4—H4	120.2	C11—C12—C13	118.46 (15)
C3—C4—C5	119.67 (14)	C13—C12—H12	120.8
C5—C4—H4	120.2	C12—C13—H13	120.0
C4—C5—C6	122.82 (15)	C14—C13—C12	120.06 (15)
C4—C5—C10	117.69 (15)	C14—C13—H13	120.0
C6—C5—C10	119.49 (15)	C13—C14—Cl1	118.80 (13)
C5—C6—H6	120.0	C13—C14—C15	121.52 (16)
C7—C6—C5	119.96 (15)	C15—C14—Cl1	119.68 (14)
C7—C6—H6	120.0	C14—C15—H15	120.6
C6—C7—H7	119.7	C14—C15—C16	118.71 (16)
C6—C7—C8	120.66 (16)	C16—C15—H15	120.6
C8—C7—H7	119.7	C11—C16—C15	119.99 (15)
C7—C8—H8	119.6	C11—C16—H16	120.0
C9—C8—C7	120.89 (16)	C15—C16—H16	120.0
Cl1—C14—C15—C16	−179.15 (12)	C5—C6—C7—C8	0.2 (3)
O1—C1—C2—N1	162.83 (16)	C6—C5—C10—N1	−178.71 (14)
O1—C1—C2—C3	−16.9 (2)	C6—C5—C10—C9	1.5 (2)
O2—C1—C2—N1	−17.4 (2)	C6—C7—C8—C9	0.8 (3)
O2—C1—C2—C3	162.86 (14)	C7—C8—C9—C10	−0.7 (2)
O2—C11—C12—C13	177.89 (14)	C8—C9—C10—N1	179.69 (14)
O2—C11—C16—C15	−177.73 (14)	C8—C9—C10—C5	−0.5 (2)
N1—C2—C3—C4	1.4 (2)	C10—N1—C2—C1	−179.29 (13)
C1—O2—C11—C12	36.5 (2)	C10—N1—C2—C3	0.4 (2)
C1—O2—C11—C16	−147.26 (15)	C10—C5—C6—C7	−1.3 (2)
C1—C2—C3—C4	−178.90 (14)	C11—O2—C1—O1	−3.2 (2)
C2—N1—C10—C5	−1.7 (2)	C11—O2—C1—C2	177.06 (13)
C2—N1—C10—C9	178.15 (14)	C11—C12—C13—C14	−1.0 (2)
C2—C3—C4—C5	−1.9 (2)	C12—C11—C16—C15	−1.4 (2)
C3—C4—C5—C6	−179.43 (15)	C12—C13—C14—Cl1	179.69 (13)
C3—C4—C5—C10	0.7 (2)	C12—C13—C14—C15	−0.4 (3)
C4—C5—C6—C7	178.84 (16)	C13—C14—C15—C16	1.0 (3)
C4—C5—C10—N1	1.1 (2)	C14—C15—C16—C11	−0.1 (2)
C4—C5—C10—C9	−178.68 (14)	C16—C11—C12—C13	1.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1i	0.93	2.42	3.250 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1i	0.93	2.42	3.250 (2)	148

Symmetry code: (i) .