Crystal structure of ethyl 2-chloro-6-methyl-quinoline-3-carboxyl-ate.

In the title compound, C13H12ClNO2, the dihedral angle between the planes of the quinoline ring system (r.m.s. deviation = 0.029 Å) and the ester group is 54.97 (6)°. The C-O-C-Cm (m = meth-yl) torsion angle is -140.62 (16)°. In the crystal, mol-ecules inter-act via aromatic π-π stacking [shortest centroid-centroid separation = 3.6774 (9) Å] generating (010) sheets.

Related literature

For background to 2-chloro-3-formyl­quinolines, see: Michael (2004 ▶); Abdel-Wahab et al. (2012 ▶). For our previous work in this area, see: Benzerka et al. (2012 ▶, 2013 ▶).

Experimental

Crystal data

C13H12ClNO2

M = 249.69

Triclinic,

a = 6.0391 (5) Å

b = 7.2986 (6) Å

c = 13.4323 (12) Å

α = 98.238 (6)°

β = 90.123 (5)°

γ = 96.429 (6)°

V = 582.16 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 150 K

0.18 × 0.14 × 0.12 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.690, T max = 0.747

5190 measured reflections

2061 independent reflections

1872 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.078

S = 1.06

2061 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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 (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814016900/hb7259sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016900/hb7259Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016900/hb7259Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814016900/hb7259fig1.tif

The structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S1600536814016900/hb7259fig2.tif

A diagram of the layered crystal packing of (I) viewed down the a axis.

CCDC reference: 1015360

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

C13H12ClNO2	Z = 2
Mr = 249.69	F(000) = 260
Triclinic, P1	Dx = 1.424 Mg m−3
a = 6.0391 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.2986 (6) Å	Cell parameters from 2875 reflections
c = 13.4323 (12) Å	θ = 2.8–25.0°
α = 98.238 (6)°	µ = 0.32 mm−1
β = 90.123 (5)°	T = 150 K
γ = 96.429 (6)°	BLOCK, colourless
V = 582.16 (9) Å3	0.18 × 0.14 × 0.12 mm

Bruker APEXII diffractometer	1872 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
CCD rotation images, thin slices scans	θmax = 25.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −7→7
Tmin = 0.690, Tmax = 0.747	k = −8→8
5190 measured reflections	l = −16→15
2061 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0383P)2 + 0.2333P] where P = (Fo2 + 2Fc2)/3
2061 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.20 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
C10	0.6109 (2)	0.4100 (2)	0.31856 (11)	0.0233 (3)
C11	0.7716 (3)	0.2270 (2)	−0.23686 (11)	0.0281 (4)
H11A	0.7218	0.3141	−0.2768	0.042*
H11B	0.7582	0.105	−0.2757	0.042*
H11C	0.9246	0.2644	−0.2169	0.042*
C12	0.7931 (3)	0.6667 (2)	0.42998 (12)	0.0356 (4)
H12A	0.9531	0.6636	0.4327	0.043*
H12B	0.7258	0.5967	0.4805	0.043*
C13	0.7400 (4)	0.8609 (3)	0.44891 (14)	0.0491 (5)
H13A	0.8105	0.9297	0.3995	0.074*
H13B	0.7934	0.9171	0.5149	0.074*
H13C	0.5815	0.8625	0.4447	0.074*
O1	0.70435 (19)	0.58589 (15)	0.33028 (8)	0.0290 (3)
O2	0.6007 (2)	0.31046 (17)	0.38231 (9)	0.0374 (3)
C1	0.3008 (2)	0.27029 (19)	0.19204 (11)	0.0204 (3)
C2	0.5237 (2)	0.35132 (19)	0.21333 (11)	0.0203 (3)
C3	0.6587 (2)	0.36577 (19)	0.13282 (11)	0.0209 (3)
H3	0.804	0.4231	0.1429	0.025*
C4	0.5801 (2)	0.29487 (19)	0.03486 (11)	0.0193 (3)
C5	0.7131 (2)	0.29932 (19)	−0.05125 (11)	0.0216 (3)
H5	0.8595	0.3552	−0.0441	0.026*
C6	0.6313 (2)	0.22322 (19)	−0.14494 (11)	0.0217 (3)
C7	0.4081 (3)	0.1369 (2)	−0.15399 (11)	0.0242 (3)
H7	0.3517	0.083	−0.2172	0.029*
C8	0.2740 (2)	0.1305 (2)	−0.07286 (11)	0.0231 (3)
H8	0.1283	0.0733	−0.0812	0.028*
C9	0.3560 (2)	0.21049 (19)	0.02358 (11)	0.0198 (3)
Cl1	0.11327 (6)	0.26599 (5)	0.29105 (3)	0.02749 (13)
N1	0.2174 (2)	0.20436 (16)	0.10369 (9)	0.0218 (3)

	U11	U22	U33	U12	U13	U23
C10	0.0187 (7)	0.0291 (8)	0.0229 (8)	0.0065 (6)	0.0032 (6)	0.0034 (6)
C11	0.0327 (9)	0.0288 (8)	0.0235 (8)	0.0071 (7)	0.0035 (7)	0.0039 (6)
C12	0.0407 (10)	0.0442 (10)	0.0191 (8)	0.0002 (8)	−0.0072 (7)	−0.0014 (7)
C13	0.0723 (14)	0.0412 (11)	0.0298 (10)	0.0039 (10)	−0.0100 (9)	−0.0065 (8)
O1	0.0382 (6)	0.0265 (6)	0.0204 (5)	−0.0006 (5)	−0.0049 (5)	0.0009 (4)
O2	0.0440 (7)	0.0414 (7)	0.0278 (6)	−0.0020 (5)	−0.0028 (5)	0.0144 (5)
C1	0.0213 (7)	0.0180 (7)	0.0237 (8)	0.0053 (6)	0.0043 (6)	0.0061 (6)
C2	0.0212 (7)	0.0177 (7)	0.0231 (7)	0.0056 (6)	0.0015 (6)	0.0040 (6)
C3	0.0185 (7)	0.0188 (7)	0.0253 (8)	0.0014 (6)	−0.0005 (6)	0.0034 (6)
C4	0.0202 (7)	0.0144 (7)	0.0240 (7)	0.0040 (5)	0.0008 (6)	0.0039 (6)
C5	0.0190 (7)	0.0195 (7)	0.0270 (8)	0.0029 (6)	0.0014 (6)	0.0052 (6)
C6	0.0266 (8)	0.0169 (7)	0.0235 (7)	0.0070 (6)	0.0022 (6)	0.0058 (6)
C7	0.0306 (8)	0.0202 (7)	0.0218 (8)	0.0044 (6)	−0.0045 (6)	0.0023 (6)
C8	0.0217 (7)	0.0193 (7)	0.0279 (8)	0.0002 (6)	−0.0031 (6)	0.0043 (6)
C9	0.0209 (7)	0.0155 (7)	0.0241 (7)	0.0043 (5)	0.0005 (6)	0.0053 (6)
Cl1	0.0230 (2)	0.0336 (2)	0.0276 (2)	0.00604 (15)	0.00824 (15)	0.00777 (16)
N1	0.0200 (6)	0.0194 (6)	0.0267 (7)	0.0027 (5)	0.0020 (5)	0.0052 (5)

C10—O2	1.1971 (18)	C1—C2	1.419 (2)
C10—O1	1.3308 (18)	C1—Cl1	1.7501 (14)
C10—C2	1.494 (2)	C2—C3	1.365 (2)
C11—C6	1.501 (2)	C3—C4	1.404 (2)
C11—H11A	0.96	C3—H3	0.93
C11—H11B	0.96	C4—C5	1.411 (2)
C11—H11C	0.96	C4—C9	1.421 (2)
C12—O1	1.4588 (19)	C5—C6	1.368 (2)
C12—C13	1.475 (3)	C5—H5	0.93
C12—H12A	0.97	C6—C7	1.420 (2)
C12—H12B	0.97	C7—C8	1.362 (2)
C13—H13A	0.96	C7—H7	0.93
C13—H13B	0.96	C8—C9	1.407 (2)
C13—H13C	0.96	C8—H8	0.93
C1—N1	1.2935 (19)	C9—N1	1.3673 (19)
O2—C10—O1	125.26 (14)	C3—C2—C1	116.71 (13)
O2—C10—C2	124.26 (14)	C3—C2—C10	121.18 (13)
O1—C10—C2	110.47 (12)	C1—C2—C10	122.05 (13)
C6—C11—H11A	109.5	C2—C3—C4	120.61 (13)
C6—C11—H11B	109.5	C2—C3—H3	119.7
H11A—C11—H11B	109.5	C4—C3—H3	119.7
C6—C11—H11C	109.5	C3—C4—C5	123.51 (13)
H11A—C11—H11C	109.5	C3—C4—C9	117.37 (13)
H11B—C11—H11C	109.5	C5—C4—C9	119.10 (13)
O1—C12—C13	107.55 (14)	C6—C5—C4	121.45 (13)
O1—C12—H12A	110.2	C6—C5—H5	119.3
C13—C12—H12A	110.2	C4—C5—H5	119.3
O1—C12—H12B	110.2	C5—C6—C7	118.37 (13)
C13—C12—H12B	110.2	C5—C6—C11	121.79 (13)
H12A—C12—H12B	108.5	C7—C6—C11	119.84 (13)
C12—C13—H13A	109.5	C8—C7—C6	121.99 (14)
C12—C13—H13B	109.5	C8—C7—H7	119
H13A—C13—H13B	109.5	C6—C7—H7	119
C12—C13—H13C	109.5	C7—C8—C9	119.98 (14)
H13A—C13—H13C	109.5	C7—C8—H8	120
H13B—C13—H13C	109.5	C9—C8—H8	120
C10—O1—C12	117.45 (12)	N1—C9—C8	118.90 (13)
N1—C1—C2	125.71 (13)	N1—C9—C4	122.00 (13)
N1—C1—Cl1	115.40 (11)	C8—C9—C4	119.10 (13)
C2—C1—Cl1	118.82 (11)	C1—N1—C9	117.48 (12)
O2—C10—O1—C12	−2.8 (2)	C9—C4—C5—C6	−0.4 (2)
C2—C10—O1—C12	178.41 (12)	C4—C5—C6—C7	−0.6 (2)
C13—C12—O1—C10	−140.62 (16)	C4—C5—C6—C11	−179.88 (13)
N1—C1—C2—C3	2.2 (2)	C5—C6—C7—C8	1.0 (2)
Cl1—C1—C2—C3	−174.62 (10)	C11—C6—C7—C8	−179.76 (13)
N1—C1—C2—C10	−174.93 (13)	C6—C7—C8—C9	−0.2 (2)
Cl1—C1—C2—C10	8.23 (18)	C7—C8—C9—N1	179.20 (12)
O2—C10—C2—C3	−123.43 (17)	C7—C8—C9—C4	−0.9 (2)
O1—C10—C2—C3	55.34 (18)	C3—C4—C9—N1	2.7 (2)
O2—C10—C2—C1	53.6 (2)	C5—C4—C9—N1	−178.89 (12)
O1—C10—C2—C1	−127.63 (14)	C3—C4—C9—C8	−177.25 (12)
C1—C2—C3—C4	−2.9 (2)	C5—C4—C9—C8	1.2 (2)
C10—C2—C3—C4	174.25 (12)	C2—C1—N1—C9	1.0 (2)
C2—C3—C4—C5	−177.71 (13)	Cl1—C1—N1—C9	177.90 (9)
C2—C3—C4—C9	0.7 (2)	C8—C9—N1—C1	176.48 (12)
C3—C4—C5—C6	177.92 (13)	C4—C9—N1—C1	−3.4 (2)