Methyl 6-chloro-2-methyl-4-phenyl­quinoline-3-carboxyl­ate

Sundar, J.K.; Natarajan, S.; Sarveswari, S.; Vijayakumar, V.; Suresh, J.; Lakshman, P.L.N.

doi:10.1107/S1600536809052891

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o169

doi:10.1107/S1600536809052891

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Methyl 6-chloro-2-methyl-4-phenylquinoline-3-carboxylate

J. Kalyana Sundar,^a S. Natarajan,^a S. Sarveswari,^b V. Vijayakumar,^b J. Suresh ^c and P. L. Nilantha Lakshman ^d ^*

^aDepartment of Physics, Madurai Kamaraj University, Madurai 625 021, India, ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India, ^cDepartment of Physics, The Madura College, Madurai 625 011, India, and ^dDepartment of Food Science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: nilanthalakshman@yahoo.co.uk

(Received 1 December 2009; accepted 9 December 2009; online 16 December 2009)

In the title compound, C₁₈H₁₄ClNO₂, the quinoline ring system is planar (r.m.s. deviation = 0.032 Å) and the phenyl ring is twisted away from it by 57.5 (1)°. The crystal structure is stabilized by weak C—H⋯π interactions.

Related literature

For the anti-tuberculosis activity of quinoline-2-carboxylic acid derivatives, see: Jain et al. (2005 ).

Experimental

Crystal data

C₁₈H₁₄ClNO₂
M_r = 311.75
Monoclinic, P 2₁ /n
a = 10.828 (5) Å
b = 7.535 (4) Å
c = 18.829 (5) Å
β = 94.369 (5)°
V = 1531.8 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 K
0.18 × 0.16 × 0.13 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.955, T_max = 0.967
3320 measured reflections
2682 independent reflections
2309 reflections with I > 2σ(I)
R_int = 0.018
2 standard reflections every 2 min
intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.100
S = 1.03
2682 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯Cg1ⁱ	0.96	2.80	3.744 (3)	166
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C14–C19 ring.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052891/ci2981sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052891/ci2981Isup2.hkl

checkCIF report

Comment top

Quinoline-2-carboxylic acid derivatives are a class of important materials useful as anti-tuberculosis agents (Jain et al., 2005). We report here the crystal structure of the title compound, a quinoline derivative.

The molecular structure of the title compound is shown in Fig.1. The quinoline ring system is planar (r.m.s. deviation is 0.032 Å). Due to phenyl substitution in the pyridine ring, the C4—C5 bond is longer [1.373 (2) Å] and the C3—C4 bond is shorter [1.434 (2) Å] than standard values for C═C (1.334 Å) and C_sp²—C_sp² (1.455 Å) bond lengths respectively. The phenyl ring is twisted out of the quinoline ring system by 57.5 (1)°. A weak C—H···π interaction involving the C14–C19 ring is observed.

Related literature top

For the anti-tuberculosis activity of quinoline-2-carboxylic acid derivatives, see: Jain et al. (2005).

Experimental top

A mixture of 2-amino-5-chlorobenzophenone (2.3 g, 0.01 mol) and methyacetoacetate (1.2 g, 0.01 mmol) with 0.15 ml concentrated HCl taken in a beaker was subjected to microwave irradiation for about 6 min. After completion of the reaction (TLC), the reaction mixture was washed with saturated NaHCO₃ solution (10 ml), dried, washed with petroleum ether and recrystallized with chloroform (m.p. 134–135 °C).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Methyl 6-chloro-2-methyl-4-phenylquinoline-3-carboxylate top

Crystal data top

C₁₈H₁₄ClNO₂	F(000) = 648
M_r = 311.75	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 10.828 (5) Å	θ = 2–25°
b = 7.535 (4) Å	µ = 0.26 mm⁻¹
c = 18.829 (5) Å	T = 293 K
β = 94.369 (5)°	Block, colourless
V = 1531.8 (12) Å³	0.18 × 0.16 × 0.13 mm
Z = 4

Data collection top

Nonius MACH-3 diffractometer	2309 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.018
Graphite monochromator	θ_max = 25.0°, θ_min = 2.1°
ω–2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = −1→8
T_min = 0.955, T_max = 0.967	l = −22→22
3320 measured reflections	2 standard reflections every 60 min
2682 independent reflections	intensity decay: none

Refinement top

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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0502P)² + 0.5537P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2682 reflections	Δρ_max = 0.20 e Å⁻³
202 parameters	Δρ_min = −0.29 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: 0.0132 (14)

Crystal data top

C₁₈H₁₄ClNO₂	V = 1531.8 (12) Å³
M_r = 311.75	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.828 (5) Å	µ = 0.26 mm⁻¹
b = 7.535 (4) Å	T = 293 K
c = 18.829 (5) Å	0.18 × 0.16 × 0.13 mm
β = 94.369 (5)°

Data collection top

Nonius MACH-3 diffractometer	2309 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.018
T_min = 0.955, T_max = 0.967	2 standard reflections every 60 min
3320 measured reflections	intensity decay: none
2682 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
2682 reflections	Δρ_min = −0.29 e Å⁻³
202 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C2	0.46859 (14)	0.2554 (2)	−0.02447 (8)	0.0362 (3)
C3	0.53086 (13)	0.25646 (19)	0.04444 (8)	0.0346 (3)
C4	0.46120 (13)	0.30371 (19)	0.10339 (8)	0.0339 (3)
C5	0.33707 (13)	0.33626 (19)	0.08882 (8)	0.0340 (3)
C6	0.28365 (13)	0.3408 (2)	0.01735 (8)	0.0358 (3)
C7	0.15150 (15)	0.3971 (3)	0.00113 (10)	0.0487 (4)
H7A	0.1384	0.4275	−0.0484	0.073*
H7B	0.1343	0.4985	0.0297	0.073*
H7C	0.0973	0.3015	0.0117	0.073*
C8	0.25152 (14)	0.3699 (2)	0.14669 (8)	0.0410 (4)
C9	0.0887 (2)	0.2382 (3)	0.20546 (13)	0.0727 (6)
H9A	0.1254	0.2793	0.2505	0.109*
H9B	0.0525	0.1233	0.2114	0.109*
H9C	0.0257	0.3200	0.1878	0.109*
C10	0.53354 (17)	0.2038 (2)	−0.08359 (9)	0.0485 (4)
H10	0.4928	0.2031	−0.1289	0.058*
C11	0.65448 (17)	0.1555 (2)	−0.07501 (10)	0.0529 (5)
H11	0.6968	0.1224	−0.1141	0.063*
C12	0.71432 (14)	0.1561 (2)	−0.00690 (11)	0.0472 (4)
C13	0.65654 (14)	0.2040 (2)	0.05190 (9)	0.0427 (4)
H13	0.6994	0.2022	0.0966	0.051*
C14	0.52259 (14)	0.3155 (2)	0.17690 (8)	0.0386 (4)
C15	0.62527 (15)	0.4262 (2)	0.19060 (9)	0.0451 (4)
H15	0.6545	0.4927	0.1538	0.054*
C16	0.68357 (17)	0.4376 (3)	0.25823 (10)	0.0548 (5)
H16	0.7522	0.5109	0.2667	0.066*
C17	0.6404 (2)	0.3406 (3)	0.31331 (10)	0.0608 (5)
H17	0.6805	0.3469	0.3587	0.073*
C18	0.5376 (2)	0.2341 (3)	0.30062 (10)	0.0608 (5)
H18	0.5072	0.1710	0.3380	0.073*
C19	0.47923 (17)	0.2203 (2)	0.23292 (9)	0.0489 (4)
H19	0.4106	0.1467	0.2249	0.059*
N1	0.34737 (12)	0.30270 (18)	−0.03732 (7)	0.0394 (3)
O1	0.24231 (13)	0.50480 (19)	0.17883 (8)	0.0677 (4)
O2	0.18315 (11)	0.22595 (16)	0.15517 (7)	0.0536 (3)
Cl1	0.86967 (4)	0.09440 (7)	0.00332 (4)	0.0739 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0368 (8)	0.0318 (8)	0.0408 (8)	0.0000 (6)	0.0077 (6)	0.0017 (6)
C3	0.0317 (7)	0.0288 (7)	0.0439 (8)	0.0001 (6)	0.0060 (6)	0.0023 (6)
C4	0.0340 (7)	0.0294 (7)	0.0384 (8)	−0.0006 (6)	0.0036 (6)	0.0018 (6)
C5	0.0322 (7)	0.0302 (7)	0.0398 (8)	0.0004 (6)	0.0048 (6)	−0.0011 (6)
C6	0.0322 (7)	0.0312 (8)	0.0439 (8)	−0.0005 (6)	0.0021 (6)	−0.0014 (6)
C7	0.0339 (8)	0.0538 (11)	0.0572 (10)	0.0064 (7)	−0.0029 (7)	−0.0010 (8)
C8	0.0369 (8)	0.0427 (9)	0.0440 (9)	0.0030 (7)	0.0071 (6)	−0.0028 (7)
C9	0.0644 (13)	0.0759 (15)	0.0835 (15)	0.0002 (11)	0.0421 (11)	0.0110 (12)
C10	0.0536 (10)	0.0489 (10)	0.0445 (9)	0.0026 (8)	0.0140 (7)	−0.0021 (8)
C11	0.0532 (10)	0.0462 (10)	0.0629 (11)	0.0032 (8)	0.0287 (9)	−0.0036 (8)
C12	0.0329 (8)	0.0321 (8)	0.0786 (12)	0.0026 (6)	0.0173 (8)	0.0004 (8)
C13	0.0332 (8)	0.0362 (8)	0.0588 (10)	0.0016 (6)	0.0042 (7)	0.0026 (7)
C14	0.0359 (8)	0.0393 (9)	0.0402 (8)	0.0030 (6)	0.0005 (6)	0.0016 (7)
C15	0.0432 (9)	0.0459 (9)	0.0456 (9)	−0.0035 (7)	0.0002 (7)	0.0039 (7)
C16	0.0505 (10)	0.0550 (11)	0.0568 (10)	−0.0077 (8)	−0.0097 (8)	−0.0015 (9)
C17	0.0713 (13)	0.0643 (12)	0.0440 (10)	−0.0029 (10)	−0.0143 (9)	0.0021 (9)
C18	0.0739 (13)	0.0627 (12)	0.0445 (10)	−0.0086 (10)	−0.0030 (9)	0.0138 (9)
C19	0.0511 (10)	0.0488 (10)	0.0461 (9)	−0.0072 (8)	−0.0004 (7)	0.0076 (8)
N1	0.0374 (7)	0.0410 (7)	0.0396 (7)	0.0020 (6)	0.0013 (5)	−0.0003 (6)
O1	0.0707 (9)	0.0562 (8)	0.0804 (10)	−0.0041 (7)	0.0339 (7)	−0.0240 (7)
O2	0.0524 (7)	0.0487 (7)	0.0629 (8)	−0.0063 (6)	0.0258 (6)	−0.0024 (6)
Cl1	0.0349 (3)	0.0598 (3)	0.1295 (5)	0.0111 (2)	0.0227 (3)	−0.0040 (3)

Geometric parameters (Å, º) top

C2—N1	1.364 (2)	C9—H9C	0.96
C2—C10	1.416 (2)	C10—C11	1.357 (3)
C2—C3	1.416 (2)	C10—H10	0.93
C3—C13	1.414 (2)	C11—C12	1.392 (3)
C3—C4	1.434 (2)	C11—H11	0.93
C4—C5	1.373 (2)	C12—C13	1.361 (2)
C4—C14	1.492 (2)	C12—Cl1	1.7418 (16)
C5—C6	1.424 (2)	C13—H13	0.93
C5—C8	1.505 (2)	C14—C19	1.387 (2)
C6—N1	1.3139 (19)	C14—C15	1.398 (2)
C6—C7	1.501 (2)	C15—C16	1.380 (2)
C7—H7A	0.96	C15—H15	0.93
C7—H7B	0.96	C16—C17	1.379 (3)
C7—H7C	0.96	C16—H16	0.93
C8—O1	1.191 (2)	C17—C18	1.378 (3)
C8—O2	1.330 (2)	C17—H17	0.93
C9—O2	1.448 (2)	C18—C19	1.383 (3)
C9—H9A	0.96	C18—H18	0.93
C9—H9B	0.96	C19—H19	0.93

N1—C2—C10	117.46 (14)	C11—C10—H10	119.6
N1—C2—C3	123.08 (13)	C2—C10—H10	119.6
C10—C2—C3	119.45 (14)	C10—C11—C12	119.08 (15)
C13—C3—C2	118.49 (14)	C10—C11—H11	120.5
C13—C3—C4	123.48 (14)	C12—C11—H11	120.5
C2—C3—C4	117.97 (13)	C13—C12—C11	122.66 (15)
C5—C4—C3	117.02 (13)	C13—C12—Cl1	118.74 (15)
C5—C4—C14	122.34 (13)	C11—C12—Cl1	118.60 (13)
C3—C4—C14	120.64 (13)	C12—C13—C3	119.47 (16)
C4—C5—C6	120.93 (13)	C12—C13—H13	120.3
C4—C5—C8	122.19 (13)	C3—C13—H13	120.3
C6—C5—C8	116.88 (13)	C19—C14—C15	118.62 (15)
N1—C6—C5	122.37 (13)	C19—C14—C4	121.47 (14)
N1—C6—C7	116.85 (14)	C15—C14—C4	119.91 (14)
C5—C6—C7	120.75 (14)	C16—C15—C14	120.58 (16)
C6—C7—H7A	109.5	C16—C15—H15	119.7
C6—C7—H7B	109.5	C14—C15—H15	119.7
H7A—C7—H7B	109.5	C17—C16—C15	120.24 (17)
C6—C7—H7C	109.5	C17—C16—H16	119.9
H7A—C7—H7C	109.5	C15—C16—H16	119.9
H7B—C7—H7C	109.5	C18—C17—C16	119.57 (16)
O1—C8—O2	124.49 (15)	C18—C17—H17	120.2
O1—C8—C5	126.29 (15)	C16—C17—H17	120.2
O2—C8—C5	109.17 (13)	C17—C18—C19	120.69 (18)
O2—C9—H9A	109.5	C17—C18—H18	119.7
O2—C9—H9B	109.5	C19—C18—H18	119.7
H9A—C9—H9B	109.5	C18—C19—C14	120.28 (17)
O2—C9—H9C	109.5	C18—C19—H19	119.9
H9A—C9—H9C	109.5	C14—C19—H19	119.9
H9B—C9—H9C	109.5	C6—N1—C2	118.28 (13)
C11—C10—C2	120.85 (17)	C8—O2—C9	116.98 (15)

N1—C2—C3—C13	179.65 (14)	C10—C11—C12—Cl1	−179.82 (14)
C10—C2—C3—C13	−0.5 (2)	C11—C12—C13—C3	−0.3 (3)
N1—C2—C3—C4	2.2 (2)	Cl1—C12—C13—C3	179.26 (12)
C10—C2—C3—C4	−177.96 (14)	C2—C3—C13—C12	0.7 (2)
C13—C3—C4—C5	−174.20 (14)	C4—C3—C13—C12	177.98 (14)
C2—C3—C4—C5	3.1 (2)	C5—C4—C14—C19	54.6 (2)
C13—C3—C4—C14	5.6 (2)	C3—C4—C14—C19	−125.18 (17)
C2—C3—C4—C14	−177.17 (14)	C5—C4—C14—C15	−124.62 (17)
C3—C4—C5—C6	−6.4 (2)	C3—C4—C14—C15	55.6 (2)
C14—C4—C5—C6	173.85 (14)	C19—C14—C15—C16	1.2 (3)
C3—C4—C5—C8	174.07 (13)	C4—C14—C15—C16	−179.56 (16)
C14—C4—C5—C8	−5.7 (2)	C14—C15—C16—C17	−0.5 (3)
C4—C5—C6—N1	4.7 (2)	C15—C16—C17—C18	−0.9 (3)
C8—C5—C6—N1	−175.70 (14)	C16—C17—C18—C19	1.6 (3)
C4—C5—C6—C7	−172.83 (15)	C17—C18—C19—C14	−0.9 (3)
C8—C5—C6—C7	6.7 (2)	C15—C14—C19—C18	−0.6 (3)
C4—C5—C8—O1	77.7 (2)	C4—C14—C19—C18	−179.76 (17)
C6—C5—C8—O1	−101.9 (2)	C5—C6—N1—C2	0.7 (2)
C4—C5—C8—O2	−104.54 (17)	C7—C6—N1—C2	178.37 (14)
C6—C5—C8—O2	75.90 (17)	C10—C2—N1—C6	176.04 (14)
N1—C2—C10—C11	179.81 (16)	C3—C2—N1—C6	−4.1 (2)
C3—C2—C10—C11	0.0 (3)	O1—C8—O2—C9	2.1 (3)
C2—C10—C11—C12	0.4 (3)	C5—C8—O2—C9	−175.75 (15)
C10—C11—C12—C13	−0.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···Cg1ⁱ	0.96	2.80	3.744 (3)	166

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄ClNO₂
M_r	311.75
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.828 (5), 7.535 (4), 18.829 (5)
β (°)	94.369 (5)
V (Å³)	1531.8 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.18 × 0.16 × 0.13

Data collection
Diffractometer	Nonius MACH-3 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.955, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	3320, 2682, 2309
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.100, 1.03
No. of reflections	2682
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.29

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···Cg1ⁱ	0.96	2.80	3.744 (3)	166

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

SN thanks the DST for the FIST programme and VV thanks the DST-India for funding through the Young Scientist-Fast Track Proposal.

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