Crystal structure of ethyl 2-(3,5-di-fluoro-phen-yl)quinoline-4-carboxyl-ate.

In the title compound, C18H13F2NO2, the two rings of the quinoline system are fused almost coaxially, with a dihedral angle between their planes of 2.28 (8)°. The plane of the attached benzene ring is inclined to the plane of the quinoline system by 7.65 (7)°. The carboxyl-ate group attached to the quinoline system is in an anti-periplanar conformation. There is a short intra-molecular C-H⋯O contact involving the carbonyl group. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming chains lying in the (1-10) plane.

Related literature

For the crystal structures of related quinoline derivatives, see: Pradeep et al. (2014 ▸); Shrungesh Kumar et al. (2015 ▸).

Experimental

Crystal data

C18H13F2NO2

M = 313.29

Triclinic,

a = 8.2674 (3) Å

b = 10.0529 (4) Å

c = 10.0562 (4) Å

α = 101.193 (2)°

β = 108.616 (2)°

γ = 98.741 (2)°

V = 756.14 (5) Å3

Z = 2

Cu Kα radiation

μ = 0.90 mm−1

T = 296 K

0.30 × 0.27 × 0.25 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.763, T max = 0.799

9032 measured reflections

2482 independent reflections

2147 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.131

S = 1.05

2482 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015007677/su5120sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007677/su5120Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015007677/su5120Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015007677/su5120fig1.tif

View of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015007677/su5120fig2.tif

A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1060299

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

C18H13F2NO2	Z = 2
Mr = 313.29	F(000) = 324
Triclinic, P1	Dx = 1.376 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.2674 (3) Å	Cell parameters from 2482 reflections
b = 10.0529 (4) Å	θ = 6.1–64.4°
c = 10.0562 (4) Å	µ = 0.90 mm−1
α = 101.193 (2)°	T = 296 K
β = 108.616 (2)°	Rectangle, brown
γ = 98.741 (2)°	0.30 × 0.27 × 0.25 mm
V = 756.14 (5) Å3

Bruker X8 Proteum diffractometer	2482 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2147 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.038
Detector resolution: 10.7 pixels mm-1	θmax = 64.4°, θmin = 6.1°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −11→11
Tmin = 0.763, Tmax = 0.799	l = −11→11
9032 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0696P)2 + 0.099P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2482 reflections	Δρmax = 0.16 e Å−3
210 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC* = KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (3)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
F17	−0.07505 (13)	0.11215 (10)	0.69978 (11)	0.0832 (4)
F18	−0.21878 (16)	0.10400 (12)	0.20982 (12)	0.0993 (4)
O20	0.5498 (2)	0.83249 (15)	0.42261 (16)	0.1012 (6)
O21	0.31565 (15)	0.67459 (11)	0.26915 (12)	0.0665 (4)
N1	0.35974 (15)	0.51312 (12)	0.70955 (13)	0.0525 (4)
C2	0.48895 (19)	0.63200 (14)	0.75527 (16)	0.0520 (4)
C3	0.5941 (2)	0.67423 (17)	0.90376 (18)	0.0698 (6)
C4	0.7210 (3)	0.7948 (2)	0.9594 (2)	0.0830 (7)
C5	0.7486 (3)	0.87609 (19)	0.8681 (2)	0.0837 (7)
C6	0.6535 (2)	0.83789 (16)	0.72399 (19)	0.0682 (6)
C7	0.51962 (18)	0.71364 (14)	0.66138 (16)	0.0512 (5)
C8	0.41001 (18)	0.66272 (14)	0.51179 (16)	0.0477 (4)
C9	0.28096 (18)	0.54385 (14)	0.46942 (15)	0.0475 (4)
C10	0.25718 (17)	0.47149 (13)	0.57158 (15)	0.0458 (4)
C11	0.11409 (17)	0.34387 (13)	0.52808 (15)	0.0473 (4)
C12	0.0105 (2)	0.28135 (15)	0.38426 (17)	0.0578 (5)
C13	−0.1193 (2)	0.16400 (16)	0.35114 (17)	0.0622 (5)
C14	−0.1529 (2)	0.10394 (15)	0.45354 (19)	0.0610 (5)
C15	−0.0474 (2)	0.16870 (15)	0.59420 (18)	0.0577 (5)
C16	0.08370 (19)	0.28567 (15)	0.63472 (17)	0.0544 (5)
C19	0.4343 (2)	0.73427 (15)	0.39981 (18)	0.0573 (5)
C22	0.3365 (3)	0.7336 (2)	0.1529 (2)	0.0850 (8)
C23	0.1898 (4)	0.6564 (3)	0.0175 (3)	0.1138 (10)
H3	0.57680	0.61930	0.96470	0.0840*
H4	0.78890	0.82250	1.05790	0.1000*
H5	0.83450	0.95880	0.90700	0.1000*
H6	0.67630	0.89370	0.66540	0.0820*
H9	0.20810	0.51030	0.37230	0.0570*
H12	0.02840	0.31830	0.31080	0.0690*
H14	−0.24150	0.02450	0.42900	0.0730*
H16	0.15150	0.32560	0.73220	0.0650*
H22A	0.44750	0.72490	0.14270	0.1020*
H22B	0.33500	0.83160	0.17440	0.1020*
H23A	0.18670	0.55860	0.00140	0.1710*
H23B	0.20580	0.68790	−0.06260	0.1710*
H23C	0.08140	0.67240	0.02550	0.1710*

	U11	U22	U33	U12	U13	U23
F17	0.0858 (7)	0.0796 (7)	0.0865 (7)	−0.0067 (5)	0.0321 (6)	0.0446 (5)
F18	0.1077 (9)	0.0813 (7)	0.0655 (7)	−0.0309 (6)	0.0073 (6)	0.0027 (5)
O20	0.1060 (11)	0.0881 (9)	0.0877 (10)	−0.0363 (8)	0.0244 (8)	0.0372 (7)
O21	0.0731 (7)	0.0690 (7)	0.0589 (7)	0.0017 (5)	0.0253 (6)	0.0284 (5)
N1	0.0544 (7)	0.0478 (7)	0.0520 (7)	0.0038 (5)	0.0171 (6)	0.0154 (5)
C2	0.0507 (8)	0.0465 (7)	0.0545 (8)	0.0059 (6)	0.0162 (7)	0.0122 (6)
C3	0.0755 (11)	0.0633 (10)	0.0568 (9)	0.0024 (8)	0.0119 (8)	0.0151 (7)
C4	0.0820 (12)	0.0736 (11)	0.0620 (11)	−0.0057 (9)	0.0003 (9)	0.0091 (9)
C5	0.0757 (12)	0.0615 (10)	0.0820 (13)	−0.0157 (8)	0.0065 (10)	0.0086 (9)
C6	0.0654 (10)	0.0546 (9)	0.0720 (11)	−0.0056 (7)	0.0173 (8)	0.0156 (8)
C7	0.0478 (8)	0.0445 (7)	0.0587 (9)	0.0066 (6)	0.0186 (7)	0.0118 (6)
C8	0.0463 (7)	0.0436 (7)	0.0572 (8)	0.0086 (6)	0.0225 (6)	0.0168 (6)
C9	0.0464 (7)	0.0455 (7)	0.0497 (8)	0.0064 (6)	0.0166 (6)	0.0145 (6)
C10	0.0452 (7)	0.0428 (7)	0.0503 (8)	0.0082 (6)	0.0178 (6)	0.0145 (6)
C11	0.0454 (7)	0.0431 (7)	0.0547 (8)	0.0080 (6)	0.0187 (6)	0.0163 (6)
C12	0.0628 (9)	0.0505 (8)	0.0564 (9)	0.0002 (7)	0.0208 (7)	0.0169 (7)
C13	0.0615 (9)	0.0513 (8)	0.0595 (9)	−0.0003 (7)	0.0129 (7)	0.0079 (7)
C14	0.0540 (9)	0.0432 (8)	0.0819 (11)	0.0004 (6)	0.0227 (8)	0.0185 (7)
C15	0.0561 (9)	0.0513 (8)	0.0731 (10)	0.0075 (6)	0.0270 (8)	0.0303 (7)
C16	0.0525 (8)	0.0534 (8)	0.0567 (9)	0.0053 (6)	0.0175 (7)	0.0217 (7)
C19	0.0578 (9)	0.0518 (8)	0.0661 (10)	0.0065 (7)	0.0258 (8)	0.0227 (7)
C22	0.0999 (14)	0.0970 (14)	0.0718 (12)	0.0123 (11)	0.0406 (11)	0.0442 (10)
C23	0.1130 (18)	0.156 (2)	0.0710 (13)	0.0141 (16)	0.0238 (12)	0.0552 (14)

F17—C15	1.3611 (19)	C11—C16	1.388 (2)
F18—C13	1.3528 (19)	C12—C13	1.374 (2)
O20—C19	1.194 (2)	C13—C14	1.369 (2)
O21—C19	1.319 (2)	C14—C15	1.367 (2)
O21—C22	1.454 (2)	C15—C16	1.367 (2)
N1—C2	1.366 (2)	C22—C23	1.475 (4)
N1—C10	1.3171 (18)	C3—H3	0.9300
C2—C3	1.407 (2)	C4—H4	0.9300
C2—C7	1.421 (2)	C5—H5	0.9300
C3—C4	1.363 (3)	C6—H6	0.9300
C4—C5	1.390 (3)	C9—H9	0.9300
C5—C6	1.353 (3)	C12—H12	0.9300
C6—C7	1.418 (2)	C14—H14	0.9300
C7—C8	1.427 (2)	C16—H16	0.9300
C8—C9	1.368 (2)	C22—H22A	0.9700
C8—C19	1.497 (2)	C22—H22B	0.9700
C9—C10	1.414 (2)	C23—H23A	0.9600
C10—C11	1.492 (2)	C23—H23B	0.9600
C11—C12	1.383 (2)	C23—H23C	0.9600
C19—O21—C22	115.85 (14)	O20—C19—O21	122.45 (16)
C2—N1—C10	118.74 (12)	O20—C19—C8	124.87 (16)
N1—C2—C3	117.08 (14)	O21—C19—C8	112.65 (14)
N1—C2—C7	123.41 (13)	O21—C22—C23	107.77 (19)
C3—C2—C7	119.51 (14)	C2—C3—H3	120.00
C2—C3—C4	120.79 (16)	C4—C3—H3	120.00
C3—C4—C5	119.67 (17)	C3—C4—H4	120.00
C4—C5—C6	121.59 (19)	C5—C4—H4	120.00
C5—C6—C7	120.72 (16)	C4—C5—H5	119.00
C2—C7—C6	117.68 (14)	C6—C5—H5	119.00
C2—C7—C8	116.27 (13)	C5—C6—H6	120.00
C6—C7—C8	126.04 (14)	C7—C6—H6	120.00
C7—C8—C9	118.95 (13)	C8—C9—H9	120.00
C7—C8—C19	121.86 (13)	C10—C9—H9	120.00
C9—C8—C19	119.19 (13)	C11—C12—H12	120.00
C8—C9—C10	120.74 (13)	C13—C12—H12	120.00
N1—C10—C9	121.83 (13)	C13—C14—H14	122.00
N1—C10—C11	116.69 (12)	C15—C14—H14	122.00
C9—C10—C11	121.48 (12)	C11—C16—H16	121.00
C10—C11—C12	121.97 (13)	C15—C16—H16	121.00
C10—C11—C16	119.24 (13)	O21—C22—H22A	110.00
C12—C11—C16	118.79 (14)	O21—C22—H22B	110.00
C11—C12—C13	119.22 (14)	C23—C22—H22A	110.00
F18—C13—C12	118.35 (14)	C23—C22—H22B	110.00
F18—C13—C14	118.13 (15)	H22A—C22—H22B	108.00
C12—C13—C14	123.52 (15)	C22—C23—H23A	109.00
C13—C14—C15	115.41 (15)	C22—C23—H23B	109.00
F17—C15—C14	117.53 (14)	C22—C23—H23C	110.00
F17—C15—C16	118.38 (14)	H23A—C23—H23B	109.00
C14—C15—C16	124.09 (15)	H23A—C23—H23C	109.00
C11—C16—C15	118.97 (14)	H23B—C23—H23C	109.00
C19—O21—C22—C23	−178.32 (19)	C19—C8—C9—C10	178.34 (14)
C22—O21—C19—O20	1.5 (3)	C9—C8—C19—O21	3.7 (2)
C22—O21—C19—C8	−176.71 (15)	C7—C8—C19—O20	4.4 (3)
C10—N1—C2—C7	−0.3 (2)	C7—C8—C19—O21	−177.37 (14)
C10—N1—C2—C3	179.08 (15)	C9—C8—C19—O20	−174.49 (18)
C2—N1—C10—C9	2.1 (2)	C8—C9—C10—N1	−1.7 (2)
C2—N1—C10—C11	−177.91 (13)	C8—C9—C10—C11	178.32 (14)
N1—C2—C3—C4	−177.18 (18)	N1—C10—C11—C12	−172.73 (14)
C3—C2—C7—C6	−1.9 (2)	C9—C10—C11—C16	−172.80 (14)
C3—C2—C7—C8	178.80 (15)	N1—C10—C11—C16	7.2 (2)
N1—C2—C7—C6	177.45 (15)	C9—C10—C11—C12	7.3 (2)
N1—C2—C7—C8	−1.9 (2)	C16—C11—C12—C13	0.1 (2)
C7—C2—C3—C4	2.2 (3)	C10—C11—C12—C13	−179.96 (16)
C2—C3—C4—C5	−0.9 (3)	C10—C11—C16—C15	−179.93 (15)
C3—C4—C5—C6	−0.7 (4)	C12—C11—C16—C15	0.0 (2)
C4—C5—C6—C7	1.0 (3)	C11—C12—C13—F18	−179.73 (15)
C5—C6—C7—C2	0.3 (3)	C11—C12—C13—C14	−0.1 (3)
C5—C6—C7—C8	179.57 (18)	C12—C13—C14—C15	−0.1 (3)
C6—C7—C8—C9	−177.03 (16)	F18—C13—C14—C15	179.58 (15)
C2—C7—C8—C19	−176.71 (14)	C13—C14—C15—F17	−179.53 (15)
C2—C7—C8—C9	2.2 (2)	C13—C14—C15—C16	0.2 (3)
C6—C7—C8—C19	4.0 (3)	F17—C15—C16—C11	179.57 (14)
C7—C8—C9—C10	−0.6 (2)	C14—C15—C16—C11	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O20	0.93	2.24	2.861 (2)	123
C14—H14···O20i	0.93	2.36	3.275 (2)	167

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C6H6O20	0.93	2.24	2.861(2)	123
C14H14O20i	0.93	2.36	3.275(2)	167

Symmetry code: (i) .