Ethyl 2,6-dichloro-4-phenyl-quinoline-3-carboxyl-ate.

In the title compound, C(18)H(13)Cl(2)NO(2), the quinoline ring system is almost planar (r.m.s. deviation 0.009 Å), and the phenyl and carboxyl-ate planes are twisted away from it by 59.2 (1) and 65.9 (2)°, respectively.

Related literature

The title compound is a 6-chloro analouge of ethyl 2-chloro-4-phenyl­quinoline-3-carboxyl­ate, which has been examined for endothelin binding affinity; for details, see: Anzini et al. (1991 ▶, 1992 ▶, 2001 ▶); Cappelli et al. (2008 ▶); Pittala et al. (2008 ▶).

Experimental

Crystal data

C18H13Cl2NO2

M = 346.19

Triclinic,

a = 8.3553 (3) Å

b = 10.1861 (5) Å

c = 10.6731 (6) Å

α = 110.537 (5)°

β = 101.421 (4)°

γ = 95.980 (4)°

V = 818.73 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.40 mm−1

T = 295 K

0.34 × 0.26 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.875, T max = 0.906

18102 measured reflections

3700 independent reflections

2537 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.144

S = 1.02

3700 reflections

209 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045334/ci2954sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045334/ci2954Isup2.hkl

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

C18H13Cl2NO2	Z = 2
Mr = 346.19	F(000) = 356
Triclinic, P1	Dx = 1.404 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3553 (3) Å	Cell parameters from 1235 reflections
b = 10.1861 (5) Å	θ = 1.7–21.3°
c = 10.6731 (6) Å	µ = 0.40 mm−1
α = 110.537 (5)°	T = 295 K
β = 101.421 (4)°	Block, colourless
γ = 95.980 (4)°	0.34 × 0.26 × 0.25 mm
V = 818.73 (7) Å3

Bruker SMART CCD area-detector diffractometer	3700 independent reflections
Radiation source: fine-focus sealed tube	2537 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.875, Tmax = 0.906	k = −13→12
18102 measured reflections	l = −13→13

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.07P)2 + 0.2927P] where P = (Fo2 + 2Fc2)/3
3700 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.41 e Å−3
1 restraint	Δρmin = −0.35 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.38082 (9)	0.27696 (7)	0.20007 (7)	0.0656 (2)
Cl2	0.09541 (10)	0.80809 (9)	0.87358 (6)	0.0737 (3)
N1	0.2968 (2)	0.38235 (19)	0.42803 (19)	0.0464 (4)
O1	0.4425 (2)	0.66274 (18)	0.20689 (15)	0.0522 (4)
O2	0.2357 (2)	0.48698 (19)	0.05569 (16)	0.0651 (5)
C1	0.3141 (3)	0.4086 (2)	0.3210 (2)	0.0432 (5)
C2	0.2874 (3)	0.5342 (2)	0.2978 (2)	0.0394 (5)
C3	0.2357 (3)	0.6384 (2)	0.3963 (2)	0.0372 (5)
C4	0.2145 (3)	0.6144 (2)	0.5166 (2)	0.0381 (5)
C5	0.1637 (3)	0.7137 (2)	0.6250 (2)	0.0436 (5)
H5	0.1397	0.7989	0.6195	0.052*
C6	0.1503 (3)	0.6832 (3)	0.7373 (2)	0.0479 (5)
C7	0.1808 (3)	0.5550 (3)	0.7485 (2)	0.0534 (6)
H7	0.1695	0.5368	0.8261	0.064*
C8	0.2271 (3)	0.4575 (3)	0.6448 (2)	0.0509 (6)
H8	0.2459	0.3714	0.6512	0.061*
C9	0.2472 (3)	0.4845 (2)	0.5278 (2)	0.0421 (5)
C10	0.2017 (3)	0.7710 (2)	0.3758 (2)	0.0399 (5)
C11	0.0839 (3)	0.7647 (3)	0.2608 (2)	0.0479 (5)
H11	0.0235	0.6769	0.1963	0.057*
C12	0.0565 (3)	0.8896 (3)	0.2421 (3)	0.0607 (7)
H12	−0.0235	0.8855	0.1659	0.073*
C13	0.1478 (4)	1.0192 (3)	0.3363 (3)	0.0650 (7)
H13	0.1301	1.1024	0.3227	0.078*
C14	0.2633 (4)	1.0268 (3)	0.4490 (3)	0.0641 (7)
H14	0.3240	1.1151	0.5123	0.077*
C15	0.2910 (3)	0.9030 (2)	0.4697 (2)	0.0506 (6)
H15	0.3701	0.9088	0.5472	0.061*
C16	0.3163 (3)	0.5558 (2)	0.1716 (2)	0.0443 (5)
C17	0.4740 (4)	0.7060 (3)	0.0971 (3)	0.0749 (9)
H17A	0.3713	0.6852	0.0267	0.090*
H17B	0.5522	0.6533	0.0547	0.090*
C18	0.5432 (6)	0.8615 (3)	0.1550 (4)	0.1137 (15)
H18A	0.5572	0.8916	0.0815	0.170*
H18B	0.6490	0.8806	0.2195	0.170*
H18C	0.4683	0.9129	0.2016	0.170*

	U11	U22	U33	U12	U13	U23
Cl1	0.0792 (5)	0.0546 (4)	0.0702 (4)	0.0224 (3)	0.0354 (4)	0.0209 (3)
Cl2	0.0878 (5)	0.1001 (6)	0.0420 (3)	0.0331 (4)	0.0288 (3)	0.0264 (3)
N1	0.0512 (11)	0.0404 (10)	0.0507 (11)	0.0064 (8)	0.0109 (9)	0.0226 (8)
O1	0.0616 (10)	0.0593 (10)	0.0393 (8)	0.0039 (8)	0.0178 (7)	0.0223 (7)
O2	0.0851 (13)	0.0648 (11)	0.0359 (9)	0.0015 (10)	0.0110 (9)	0.0135 (8)
C1	0.0424 (12)	0.0393 (11)	0.0472 (12)	0.0081 (9)	0.0125 (9)	0.0148 (9)
C2	0.0419 (12)	0.0405 (11)	0.0377 (10)	0.0071 (9)	0.0108 (9)	0.0170 (8)
C3	0.0372 (11)	0.0390 (11)	0.0361 (10)	0.0051 (9)	0.0072 (8)	0.0167 (8)
C4	0.0366 (11)	0.0431 (11)	0.0348 (10)	0.0053 (9)	0.0062 (8)	0.0171 (8)
C5	0.0448 (12)	0.0528 (13)	0.0375 (11)	0.0119 (10)	0.0111 (9)	0.0210 (9)
C6	0.0428 (12)	0.0664 (15)	0.0338 (11)	0.0074 (11)	0.0098 (9)	0.0189 (10)
C7	0.0545 (14)	0.0694 (16)	0.0382 (12)	−0.0051 (12)	0.0054 (10)	0.0309 (11)
C8	0.0577 (15)	0.0511 (13)	0.0479 (13)	0.0015 (11)	0.0063 (11)	0.0298 (11)
C9	0.0406 (12)	0.0441 (11)	0.0423 (11)	0.0017 (9)	0.0065 (9)	0.0212 (9)
C10	0.0461 (12)	0.0414 (11)	0.0398 (11)	0.0128 (9)	0.0176 (9)	0.0193 (9)
C11	0.0505 (14)	0.0519 (13)	0.0484 (12)	0.0093 (10)	0.0132 (10)	0.0272 (10)
C12	0.0577 (16)	0.0768 (19)	0.0698 (16)	0.0248 (14)	0.0205 (13)	0.0486 (15)
C13	0.0747 (19)	0.0517 (15)	0.091 (2)	0.0255 (14)	0.0355 (16)	0.0417 (15)
C14	0.0769 (19)	0.0414 (13)	0.0749 (18)	0.0124 (13)	0.0264 (15)	0.0191 (12)
C15	0.0595 (15)	0.0447 (12)	0.0461 (12)	0.0109 (11)	0.0142 (11)	0.0148 (10)
C16	0.0535 (14)	0.0451 (12)	0.0397 (12)	0.0166 (11)	0.0175 (10)	0.0173 (9)
C17	0.115 (2)	0.0674 (17)	0.0481 (14)	−0.0004 (16)	0.0374 (15)	0.0240 (13)
C18	0.189 (4)	0.082 (2)	0.075 (2)	−0.008 (3)	0.052 (3)	0.0349 (18)

Cl1—C1	1.732 (2)	C8—C9	1.407 (3)
Cl2—C6	1.742 (2)	C8—H8	0.93
N1—C1	1.292 (3)	C10—C15	1.385 (3)
N1—C9	1.369 (3)	C10—C11	1.390 (3)
O1—C16	1.325 (3)	C11—C12	1.389 (3)
O1—C17	1.448 (3)	C11—H11	0.93
O2—C16	1.199 (3)	C12—C13	1.375 (4)
C1—C2	1.417 (3)	C12—H12	0.93
C2—C3	1.382 (3)	C13—C14	1.358 (4)
C2—C16	1.499 (3)	C13—H13	0.93
C3—C4	1.429 (3)	C14—C15	1.389 (4)
C3—C10	1.488 (3)	C14—H14	0.93
C4—C5	1.416 (3)	C15—H15	0.93
C4—C9	1.419 (3)	C17—C18	1.485 (2)
C5—C6	1.361 (3)	C17—H17A	0.97
C5—H5	0.93	C17—H17B	0.97
C6—C7	1.397 (4)	C18—H18A	0.96
C7—C8	1.356 (4)	C18—H18B	0.96
C7—H7	0.93	C18—H18C	0.96
C1—N1—C9	117.23 (18)	C11—C10—C3	120.90 (19)
C16—O1—C17	116.36 (18)	C12—C11—C10	120.0 (2)
N1—C1—C2	125.8 (2)	C12—C11—H11	120.0
N1—C1—Cl1	115.05 (16)	C10—C11—H11	120.0
C2—C1—Cl1	119.09 (17)	C13—C12—C11	120.0 (2)
C3—C2—C1	118.10 (19)	C13—C12—H12	120.0
C3—C2—C16	120.40 (18)	C11—C12—H12	120.0
C1—C2—C16	121.50 (19)	C14—C13—C12	120.6 (2)
C2—C3—C4	118.21 (18)	C14—C13—H13	119.7
C2—C3—C10	120.49 (18)	C12—C13—H13	119.7
C4—C3—C10	121.30 (18)	C13—C14—C15	120.1 (3)
C5—C4—C9	118.57 (19)	C13—C14—H14	120.0
C5—C4—C3	123.39 (19)	C15—C14—H14	120.0
C9—C4—C3	118.04 (19)	C10—C15—C14	120.5 (2)
C6—C5—C4	119.4 (2)	C10—C15—H15	119.8
C6—C5—H5	120.3	C14—C15—H15	119.8
C4—C5—H5	120.3	O2—C16—O1	125.1 (2)
C5—C6—C7	122.4 (2)	O2—C16—C2	124.8 (2)
C5—C6—Cl2	119.40 (19)	O1—C16—C2	110.14 (18)
C7—C6—Cl2	118.20 (17)	O1—C17—C18	109.4 (2)
C8—C7—C6	119.2 (2)	O1—C17—H17A	109.8
C8—C7—H7	120.4	C18—C17—H17A	109.8
C6—C7—H7	120.4	O1—C17—H17B	109.8
C7—C8—C9	121.1 (2)	C18—C17—H17B	109.8
C7—C8—H8	119.5	H17A—C17—H17B	108.2
C9—C8—H8	119.5	C17—C18—H18A	109.5
N1—C9—C8	118.0 (2)	C17—C18—H18B	109.5
N1—C9—C4	122.57 (19)	H18A—C18—H18B	109.5
C8—C9—C4	119.4 (2)	C17—C18—H18C	109.5
C15—C10—C11	118.9 (2)	H18A—C18—H18C	109.5
C15—C10—C3	120.20 (19)	H18B—C18—H18C	109.5
C9—N1—C1—C2	0.5 (3)	C7—C8—C9—C4	−1.6 (3)
C9—N1—C1—Cl1	178.84 (15)	C5—C4—C9—N1	179.98 (19)
N1—C1—C2—C3	−1.1 (3)	C3—C4—C9—N1	−0.4 (3)
Cl1—C1—C2—C3	−179.37 (16)	C5—C4—C9—C8	0.5 (3)
N1—C1—C2—C16	178.0 (2)	C3—C4—C9—C8	−179.88 (19)
Cl1—C1—C2—C16	−0.3 (3)	C2—C3—C10—C15	−119.8 (2)
C1—C2—C3—C4	0.8 (3)	C4—C3—C10—C15	60.9 (3)
C16—C2—C3—C4	−178.25 (19)	C2—C3—C10—C11	58.2 (3)
C1—C2—C3—C10	−178.5 (2)	C4—C3—C10—C11	−121.1 (2)
C16—C2—C3—C10	2.4 (3)	C15—C10—C11—C12	−0.5 (3)
C2—C3—C4—C5	179.40 (19)	C3—C10—C11—C12	−178.6 (2)
C10—C3—C4—C5	−1.3 (3)	C10—C11—C12—C13	1.0 (4)
C2—C3—C4—C9	−0.2 (3)	C11—C12—C13—C14	−0.9 (4)
C10—C3—C4—C9	179.14 (19)	C12—C13—C14—C15	0.3 (4)
C9—C4—C5—C6	1.1 (3)	C11—C10—C15—C14	−0.1 (4)
C3—C4—C5—C6	−178.5 (2)	C3—C10—C15—C14	178.0 (2)
C4—C5—C6—C7	−1.7 (3)	C13—C14—C15—C10	0.2 (4)
C4—C5—C6—Cl2	177.61 (16)	C17—O1—C16—O2	5.6 (3)
C5—C6—C7—C8	0.7 (4)	C17—O1—C16—C2	−173.7 (2)
Cl2—C6—C7—C8	−178.63 (18)	C3—C2—C16—O2	−114.0 (3)
C6—C7—C8—C9	1.0 (4)	C1—C2—C16—O2	66.9 (3)
C1—N1—C9—C8	179.8 (2)	C3—C2—C16—O1	65.3 (3)
C1—N1—C9—C4	0.3 (3)	C1—C2—C16—O1	−113.8 (2)
C7—C8—C9—N1	179.0 (2)	C16—O1—C17—C18	148.7 (3)