Ethyl 6-chloro-2-methyl-4-phenyl-quinoline-3-carboxyl-ate.

In the title compound, C(19)H(16)ClNO(2), the quinoline ring system is planar (r.m.s. deviation = 0.008 Å). The phenyl group and the -CO(2) fragment of the ester unit form dihedral angles of 60.0 (1) and 60.5 (1)°, respectively, with the quinoline ring system.

Related literature

For related structures, see: Baumer et al. (2001 ▶); Subashini et al. (2009 ▶).

Experimental

Crystal data

C19H16ClNO2

M = 325.78

Triclinic,

a = 8.3622 (3) Å

b = 10.1971 (3) Å

c = 10.7052 (3) Å

α = 110.440 (2)°

β = 101.588 (2)°

γ = 94.860 (2)°

V = 825.91 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 290 K

0.24 × 0.18 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.945, T max = 0.970

15008 measured reflections

3775 independent reflections

2854 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.147

S = 1.04

3775 reflections

210 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.38 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/S160053680904536X/ci2957sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904536X/ci2957Isup2.hkl

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

C19H16ClNO2	Z = 2
Mr = 325.78	F(000) = 340
Triclinic, P1	Dx = 1.310 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3622 (3) Å	Cell parameters from 1153 reflections
b = 10.1971 (3) Å	θ = 1.7–24.3°
c = 10.7052 (3) Å	µ = 0.24 mm−1
α = 110.440 (2)°	T = 290 K
β = 101.588 (2)°	Block, colourless
γ = 94.860 (2)°	0.24 × 0.18 × 0.13 mm
V = 825.91 (4) Å3

Bruker SMART CCD area-detector diffractometer	3775 independent reflections
Radiation source: fine-focus sealed tube	2854 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.945, Tmax = 0.970	k = −12→13
15008 measured reflections	l = −13→10

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0795P)2 + 0.1903P] where P = (Fo2 + 2Fc2)/3
3775 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.38 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.59565 (8)	0.80991 (7)	0.87661 (5)	0.0711 (2)
N1	0.79494 (19)	0.38099 (15)	0.42954 (15)	0.0465 (4)
O1	0.93549 (17)	0.66715 (14)	0.21071 (12)	0.0523 (3)
O2	0.7449 (2)	0.48238 (16)	0.06011 (14)	0.0690 (4)
C1	0.8150 (2)	0.40465 (18)	0.31986 (18)	0.0433 (4)
C2	0.7883 (2)	0.53430 (18)	0.30236 (17)	0.0407 (4)
C3	0.7375 (2)	0.63972 (17)	0.40021 (16)	0.0387 (4)
C4	0.71546 (19)	0.61552 (17)	0.52007 (16)	0.0387 (4)
C5	0.6644 (2)	0.7151 (2)	0.62823 (17)	0.0451 (4)
H5	0.6412	0.8009	0.6230	0.054*
C6	0.6496 (2)	0.6845 (2)	0.74006 (17)	0.0481 (4)
C7	0.6778 (2)	0.5543 (2)	0.74986 (18)	0.0523 (5)
H7	0.6647	0.5352	0.8264	0.063*
C8	0.7245 (2)	0.4561 (2)	0.64596 (19)	0.0508 (4)
H8	0.7428	0.3696	0.6520	0.061*
C9	0.7459 (2)	0.48359 (18)	0.52871 (17)	0.0422 (4)
C10	0.8700 (3)	0.2882 (2)	0.2144 (2)	0.0569 (5)
H10A	0.8926	0.2145	0.2484	0.085*
H10B	0.9685	0.3259	0.1968	0.085*
H10C	0.7839	0.2500	0.1307	0.085*
C11	0.8176 (2)	0.55604 (19)	0.17664 (18)	0.0465 (4)
C12	0.9625 (4)	0.7067 (2)	0.0980 (2)	0.0733 (7)
H12A	0.8579	0.6918	0.0321	0.088*
H12B	1.0348	0.6487	0.0514	0.088*
C13	1.0409 (5)	0.8617 (3)	0.1562 (3)	0.1064 (11)
H13A	1.0569	0.8904	0.0826	0.160*
H13B	1.1459	0.8749	0.2191	0.160*
H13C	0.9696	0.9181	0.2038	0.160*
C14	0.7035 (2)	0.77328 (18)	0.38081 (17)	0.0408 (4)
C15	0.5843 (2)	0.7689 (2)	0.26713 (19)	0.0492 (4)
H15	0.5239	0.6823	0.2036	0.059*
C16	0.5557 (3)	0.8940 (2)	0.2488 (2)	0.0609 (5)
H16	0.4755	0.8908	0.1733	0.073*
C17	0.6458 (3)	1.0230 (2)	0.3421 (3)	0.0625 (6)
H17	0.6263	1.1064	0.3293	0.075*
C18	0.7641 (3)	1.0279 (2)	0.4538 (2)	0.0629 (5)
H18	0.8251	1.1147	0.5165	0.075*
C19	0.7927 (2)	0.9034 (2)	0.4729 (2)	0.0521 (4)
H19	0.8731	0.9075	0.5487	0.063*

	U11	U22	U33	U12	U13	U23
Cl1	0.0823 (4)	0.0947 (5)	0.0429 (3)	0.0315 (3)	0.0267 (2)	0.0238 (3)
N1	0.0520 (9)	0.0403 (8)	0.0503 (8)	0.0080 (6)	0.0129 (7)	0.0206 (7)
O1	0.0608 (8)	0.0592 (8)	0.0419 (6)	0.0060 (6)	0.0191 (6)	0.0223 (6)
O2	0.0949 (12)	0.0642 (9)	0.0385 (7)	0.0010 (8)	0.0144 (7)	0.0118 (6)
C1	0.0431 (9)	0.0404 (9)	0.0472 (9)	0.0068 (7)	0.0130 (7)	0.0163 (7)
C2	0.0416 (9)	0.0427 (9)	0.0395 (8)	0.0072 (7)	0.0117 (7)	0.0164 (7)
C3	0.0387 (8)	0.0410 (9)	0.0380 (8)	0.0071 (7)	0.0089 (6)	0.0170 (7)
C4	0.0372 (8)	0.0431 (9)	0.0374 (8)	0.0062 (7)	0.0080 (6)	0.0179 (7)
C5	0.0446 (9)	0.0547 (10)	0.0413 (8)	0.0146 (8)	0.0125 (7)	0.0221 (8)
C6	0.0439 (9)	0.0630 (11)	0.0366 (8)	0.0080 (8)	0.0109 (7)	0.0176 (8)
C7	0.0528 (10)	0.0662 (12)	0.0395 (9)	−0.0035 (9)	0.0069 (7)	0.0274 (9)
C8	0.0581 (11)	0.0494 (10)	0.0470 (9)	0.0005 (8)	0.0069 (8)	0.0260 (8)
C9	0.0418 (9)	0.0440 (9)	0.0422 (8)	0.0033 (7)	0.0077 (7)	0.0201 (7)
C10	0.0645 (12)	0.0455 (10)	0.0657 (12)	0.0169 (9)	0.0276 (10)	0.0186 (9)
C11	0.0557 (10)	0.0464 (10)	0.0422 (9)	0.0155 (8)	0.0176 (8)	0.0177 (8)
C12	0.113 (2)	0.0663 (14)	0.0491 (11)	0.0044 (13)	0.0366 (12)	0.0246 (10)
C13	0.165 (3)	0.086 (2)	0.0744 (17)	−0.011 (2)	0.0446 (19)	0.0358 (15)
C14	0.0453 (9)	0.0429 (9)	0.0410 (8)	0.0124 (7)	0.0171 (7)	0.0192 (7)
C15	0.0503 (10)	0.0527 (10)	0.0515 (10)	0.0093 (8)	0.0119 (8)	0.0280 (8)
C16	0.0559 (11)	0.0731 (14)	0.0729 (13)	0.0208 (10)	0.0185 (10)	0.0469 (12)
C17	0.0709 (13)	0.0522 (12)	0.0866 (15)	0.0251 (10)	0.0355 (12)	0.0407 (11)
C18	0.0757 (14)	0.0423 (10)	0.0725 (13)	0.0136 (10)	0.0271 (11)	0.0180 (10)
C19	0.0583 (11)	0.0474 (10)	0.0488 (10)	0.0107 (8)	0.0128 (8)	0.0158 (8)

Cl1—C6	1.7414 (19)	C10—H10A	0.96
N1—C1	1.317 (2)	C10—H10B	0.96
N1—C9	1.364 (2)	C10—H10C	0.96
O1—C11	1.329 (2)	C12—C13	1.513 (2)
O1—C12	1.450 (2)	C12—H12A	0.97
O2—C11	1.206 (2)	C12—H12B	0.97
C1—C2	1.428 (2)	C13—H13A	0.96
C1—C10	1.503 (3)	C13—H13B	0.96
C2—C3	1.380 (2)	C13—H13C	0.96
C2—C11	1.501 (2)	C14—C19	1.383 (3)
C3—C4	1.432 (2)	C14—C15	1.394 (2)
C3—C14	1.489 (2)	C15—C16	1.389 (3)
C4—C5	1.416 (2)	C15—H15	0.93
C4—C9	1.421 (2)	C16—C17	1.381 (3)
C5—C6	1.364 (2)	C16—H16	0.93
C5—H5	0.93	C17—C18	1.373 (3)
C6—C7	1.404 (3)	C17—H17	0.93
C7—C8	1.362 (3)	C18—C19	1.387 (3)
C7—H7	0.93	C18—H18	0.93
C8—C9	1.419 (2)	C19—H19	0.93
C8—H8	0.93
C1—N1—C9	118.67 (14)	H10B—C10—H10C	109.5
C11—O1—C12	115.60 (15)	O2—C11—O1	124.32 (17)
N1—C1—C2	122.09 (16)	O2—C11—C2	124.75 (18)
N1—C1—C10	116.33 (15)	O1—C11—C2	110.93 (14)
C2—C1—C10	121.57 (15)	O1—C12—C13	108.36 (17)
C3—C2—C1	120.68 (15)	O1—C12—H12A	110.0
C3—C2—C11	119.90 (15)	C13—C12—H12A	110.0
C1—C2—C11	119.42 (15)	O1—C12—H12B	110.0
C2—C3—C4	117.83 (14)	C13—C12—H12B	110.0
C2—C3—C14	121.20 (14)	H12A—C12—H12B	108.4
C4—C3—C14	120.96 (14)	C12—C13—H13A	109.5
C5—C4—C9	119.10 (15)	C12—C13—H13B	109.5
C5—C4—C3	123.49 (15)	H13A—C13—H13B	109.5
C9—C4—C3	117.41 (15)	C12—C13—H13C	109.5
C6—C5—C4	119.64 (16)	H13A—C13—H13C	109.5
C6—C5—H5	120.2	H13B—C13—H13C	109.5
C4—C5—H5	120.2	C19—C14—C15	118.78 (16)
C5—C6—C7	122.02 (17)	C19—C14—C3	120.68 (15)
C5—C6—Cl1	119.74 (15)	C15—C14—C3	120.52 (16)
C7—C6—Cl1	118.23 (13)	C16—C15—C14	120.00 (18)
C8—C7—C6	119.22 (16)	C16—C15—H15	120.0
C8—C7—H7	120.4	C14—C15—H15	120.0
C6—C7—H7	120.4	C17—C16—C15	120.37 (19)
C7—C8—C9	121.19 (17)	C17—C16—H16	119.8
C7—C8—H8	119.4	C15—C16—H16	119.8
C9—C8—H8	119.4	C18—C17—C16	119.94 (18)
N1—C9—C8	117.90 (15)	C18—C17—H17	120.0
N1—C9—C4	123.31 (15)	C16—C17—H17	120.0
C8—C9—C4	118.79 (16)	C17—C18—C19	119.9 (2)
C1—C10—H10A	109.5	C17—C18—H18	120.0
C1—C10—H10B	109.5	C19—C18—H18	120.0
H10A—C10—H10B	109.5	C14—C19—C18	120.97 (19)
C1—C10—H10C	109.5	C14—C19—H19	119.5
H10A—C10—H10C	109.5	C18—C19—H19	119.5
C9—N1—C1—C2	0.5 (3)	C7—C8—C9—C4	−0.8 (3)
C9—N1—C1—C10	179.69 (16)	C5—C4—C9—N1	179.81 (15)
N1—C1—C2—C3	−1.0 (3)	C3—C4—C9—N1	0.2 (2)
C10—C1—C2—C3	179.86 (16)	C5—C4—C9—C8	−0.2 (2)
N1—C1—C2—C11	178.43 (16)	C3—C4—C9—C8	−179.76 (15)
C10—C1—C2—C11	−0.7 (3)	C12—O1—C11—O2	6.4 (3)
C1—C2—C3—C4	1.1 (2)	C12—O1—C11—C2	−174.03 (17)
C11—C2—C3—C4	−178.39 (15)	C3—C2—C11—O2	−119.9 (2)
C1—C2—C3—C14	−177.78 (15)	C1—C2—C11—O2	60.7 (3)
C11—C2—C3—C14	2.8 (2)	C3—C2—C11—O1	60.5 (2)
C2—C3—C4—C5	179.76 (15)	C1—C2—C11—O1	−118.93 (17)
C14—C3—C4—C5	−1.4 (2)	C11—O1—C12—C13	156.4 (2)
C2—C3—C4—C9	−0.7 (2)	C2—C3—C14—C19	−119.39 (19)
C14—C3—C4—C9	178.17 (15)	C4—C3—C14—C19	61.8 (2)
C9—C4—C5—C6	1.7 (3)	C2—C3—C14—C15	58.7 (2)
C3—C4—C5—C6	−178.74 (16)	C4—C3—C14—C15	−120.12 (18)
C4—C5—C6—C7	−2.3 (3)	C19—C14—C15—C16	−0.7 (3)
C4—C5—C6—Cl1	177.19 (13)	C3—C14—C15—C16	−178.83 (17)
C5—C6—C7—C8	1.3 (3)	C14—C15—C16—C17	0.5 (3)
Cl1—C6—C7—C8	−178.20 (14)	C15—C16—C17—C18	−0.1 (3)
C6—C7—C8—C9	0.3 (3)	C16—C17—C18—C19	−0.2 (3)
C1—N1—C9—C8	179.84 (16)	C15—C14—C19—C18	0.5 (3)
C1—N1—C9—C4	−0.1 (3)	C3—C14—C19—C18	178.57 (18)
C7—C8—C9—N1	179.20 (17)	C17—C18—C19—C14	0.0 (3)