Crystal structure of ethyl 2,4-di-chloro-quinoline-3-carboxyl-ate.

In the crystal structure of the title compound, C12H9Cl2NO2, the mean planes through the quinoline and carboxyl-ate groups have r.m.s. deviations of 0.006 and 0.021 Å, respectively, and form a dihedral angle of 87.06 (19)°. In the crystal, mol-ecules are linked via very weak C-H⋯O hydrogen bonds, forming chains, which propagate along the c-axis direction.

Related literature

For the potential of related compounds in anti-HIV treatment, see: Maartens et al. (2014 ▸); Hopkins et al. (2004 ▸). For a related structure, see: Reyes et al. (2013 ▸)

Experimental

Crystal data

C12H9Cl2NO2

M = 270.10

Monoclinic,

a = 8.5860 (4) Å

b = 19.9082 (11) Å

c = 7.1304 (4) Å

β = 100.262 (1)°

V = 1199.32 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.53 mm−1

T = 298 K

0.50 × 0.25 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

6785 measured reflections

2197 independent reflections

1833 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.05

2197 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2012 ▸); cell refinement: SAINT (Bruker, 2012 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2015 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015020587/nk2231sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020587/nk2231Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015020587/nk2231Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015020587/nk2231fig1.tif

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

Click here for additional data file.

. DOI: 10.1107/S2056989015020587/nk2231fig2.tif

Crystal packing viewed along the a axis. The inter­molecular C—H⋯O hydrogen bonds are shown as dashed lines.

CCDC reference: 1434378

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

C12H9Cl2NO2	F(000) = 552
Mr = 270.10	Dx = 1.496 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.5860 (4) Å	Cell parameters from 4843 reflections
b = 19.9082 (11) Å	θ = 2.4–25.4°
c = 7.1304 (4) Å	µ = 0.53 mm−1
β = 100.262 (1)°	T = 298 K
V = 1199.32 (11) Å3	Prism, colourless
Z = 4	0.50 × 0.25 × 0.16 mm

Bruker APEXII CCD area-detector diffractometer	Rint = 0.024
Detector resolution: 0.83 pixels mm-1	θmax = 25.4°, θmin = 2.1°
ω scans	h = −10→10
6785 measured reflections	k = −23→23
2197 independent reflections	l = −8→8
1833 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.052P)2 + 0.1257P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.22 e Å−3
2197 reflections	Δρmin = −0.21 e Å−3
156 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.010 (2)

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.

	x	y	z	Uiso*/Ueq
Cl1	0.85142 (7)	0.95554 (3)	0.67524 (10)	0.0847 (2)
Cl2	0.49224 (5)	0.73357 (2)	0.59388 (7)	0.05637 (19)
O1	0.48324 (17)	0.90370 (7)	0.44065 (18)	0.0701 (4)
O2	0.48524 (14)	0.89699 (6)	0.75480 (17)	0.0565 (3)
N1	0.96891 (17)	0.83536 (9)	0.7101 (2)	0.0567 (4)
C2	0.8376 (2)	0.86809 (9)	0.6757 (2)	0.0514 (4)
C3	0.68405 (18)	0.84036 (8)	0.6379 (2)	0.0435 (4)
C4	0.67539 (18)	0.77181 (8)	0.6378 (2)	0.0415 (4)
C5	0.8137 (3)	0.66071 (10)	0.6754 (3)	0.0621 (5)
H5	0.7187	0.6372	0.6505	0.075*
C6	0.9535 (3)	0.62696 (13)	0.7135 (3)	0.0816 (7)
H6	0.9531	0.5802	0.7143	0.098*
C7	1.0976 (3)	0.66121 (14)	0.7514 (3)	0.0838 (8)
H7	1.1918	0.6371	0.7779	0.101*
C8	1.1014 (2)	0.72928 (13)	0.7498 (3)	0.0705 (6)
H8	1.1981	0.7516	0.7748	0.085*
C9	0.9593 (2)	0.76660 (10)	0.7105 (2)	0.0511 (5)
C10	0.81366 (19)	0.73162 (9)	0.6738 (2)	0.0451 (4)
C11	0.5396 (2)	0.88399 (9)	0.5963 (2)	0.0478 (4)
C12	0.3434 (2)	0.93853 (11)	0.7367 (3)	0.0674 (5)
H12A	0.2575	0.9182	0.6481	0.081*
H12B	0.3638	0.9828	0.6897	0.081*
C13	0.3010 (3)	0.94358 (13)	0.9279 (3)	0.0858 (7)
H13A	0.2721	0.9000	0.9681	0.129*
H13B	0.2133	0.9738	0.9235	0.129*
H13C	0.3900	0.9602	1.0166	0.129*

	U11	U22	U33	U12	U13	U23
Cl1	0.0773 (4)	0.0613 (3)	0.1107 (5)	−0.0197 (3)	0.0034 (3)	−0.0015 (3)
Cl2	0.0445 (3)	0.0641 (3)	0.0597 (3)	−0.01024 (19)	0.0070 (2)	−0.0018 (2)
O1	0.0713 (9)	0.0848 (10)	0.0506 (8)	0.0213 (7)	0.0009 (7)	0.0096 (7)
O2	0.0498 (7)	0.0681 (8)	0.0529 (7)	0.0183 (6)	0.0129 (6)	0.0081 (6)
N1	0.0395 (8)	0.0795 (11)	0.0508 (9)	−0.0050 (7)	0.0070 (6)	−0.0022 (8)
C2	0.0455 (10)	0.0606 (11)	0.0475 (10)	−0.0066 (8)	0.0064 (8)	−0.0016 (8)
C3	0.0393 (9)	0.0544 (10)	0.0367 (8)	0.0011 (7)	0.0069 (7)	0.0000 (7)
C4	0.0377 (8)	0.0548 (10)	0.0325 (8)	−0.0016 (7)	0.0073 (6)	−0.0002 (7)
C5	0.0719 (13)	0.0630 (12)	0.0520 (11)	0.0133 (10)	0.0128 (9)	0.0027 (9)
C6	0.0980 (19)	0.0785 (15)	0.0680 (14)	0.0429 (14)	0.0143 (13)	0.0066 (11)
C7	0.0768 (16)	0.118 (2)	0.0564 (13)	0.0554 (16)	0.0110 (11)	0.0060 (13)
C8	0.0445 (11)	0.120 (2)	0.0476 (11)	0.0239 (11)	0.0085 (8)	−0.0009 (11)
C9	0.0412 (9)	0.0793 (13)	0.0337 (9)	0.0101 (8)	0.0090 (7)	−0.0001 (8)
C10	0.0451 (9)	0.0608 (11)	0.0301 (8)	0.0100 (8)	0.0088 (7)	0.0016 (7)
C11	0.0440 (9)	0.0499 (9)	0.0481 (10)	−0.0006 (7)	0.0042 (8)	0.0018 (8)
C12	0.0544 (11)	0.0706 (12)	0.0778 (13)	0.0229 (10)	0.0136 (10)	0.0079 (11)
C13	0.0641 (14)	0.1089 (19)	0.0878 (16)	0.0215 (13)	0.0227 (12)	−0.0130 (14)

Cl1—C2	1.745 (2)	C6—C7	1.396 (4)
Cl2—C4	1.7248 (16)	C6—H6	0.9300
O1—C11	1.195 (2)	C7—C8	1.356 (4)
O2—C11	1.323 (2)	C7—H7	0.9300
O2—C12	1.459 (2)	C8—C9	1.413 (3)
N1—C2	1.287 (2)	C8—H8	0.9300
N1—C9	1.371 (3)	C9—C10	1.414 (2)
C2—C3	1.411 (2)	C12—C13	1.476 (3)
C3—C4	1.367 (2)	C12—H12A	0.9700
C3—C11	1.500 (2)	C12—H12B	0.9700
C4—C10	1.417 (2)	C13—H13A	0.9600
C5—C6	1.360 (3)	C13—H13B	0.9600
C5—C10	1.412 (3)	C13—H13C	0.9600
C5—H5	0.9300
C11—O2—C12	116.84 (14)	C9—C8—H8	119.8
C2—N1—C9	117.06 (15)	N1—C9—C8	118.38 (18)
N1—C2—C3	126.55 (18)	N1—C9—C10	122.85 (15)
N1—C2—Cl1	116.62 (14)	C8—C9—C10	118.77 (19)
C3—C2—Cl1	116.83 (14)	C5—C10—C9	119.45 (16)
C4—C3—C2	116.09 (15)	C5—C10—C4	124.43 (17)
C4—C3—C11	122.35 (14)	C9—C10—C4	116.12 (16)
C2—C3—C11	121.55 (15)	O1—C11—O2	125.64 (16)
C3—C4—C10	121.33 (15)	O1—C11—C3	123.90 (16)
C3—C4—Cl2	119.25 (12)	O2—C11—C3	110.46 (14)
C10—C4—Cl2	119.42 (13)	O2—C12—C13	107.24 (16)
C6—C5—C10	119.7 (2)	O2—C12—H12A	110.3
C6—C5—H5	120.2	C13—C12—H12A	110.3
C10—C5—H5	120.2	O2—C12—H12B	110.3
C5—C6—C7	121.2 (2)	C13—C12—H12B	110.3
C5—C6—H6	119.4	H12A—C12—H12B	108.5
C7—C6—H6	119.4	C12—C13—H13A	109.5
C8—C7—C6	120.5 (2)	C12—C13—H13B	109.5
C8—C7—H7	119.7	H13A—C13—H13B	109.5
C6—C7—H7	119.7	C12—C13—H13C	109.5
C7—C8—C9	120.4 (2)	H13A—C13—H13C	109.5
C7—C8—H8	119.8	H13B—C13—H13C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.93	2.69	3.586 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.93	2.69	3.586 (3)	162

Symmetry code: (i) .