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

In the mol-ecule of the title compound, C(19)H(17)NO(2), the quinoline ring system is planar [maximum deviation 0.021 (3) Å] and oriented with respect to the phenyl ring at a dihedral angle of 80.44 (4)°. Intra-molecular C-H⋯O inter-actions result in the formation of five- and six-membered rings having planar and envelope conformations, respectively. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules into centrosymmetric dimers forming R(2) (2)(12) ring motifs. π-π contacts between the rings of the quinoline system [centroid-to-centroid distance = 3.812 (1) Å] may further stabilize the structure. Two weak C-H⋯π inter-actions are also found.

Related literature

For general background, see: Doube et al. (1998 ▶). For ring-motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H17NO2

M = 291.34

Triclinic,

a = 9.0282 (10) Å

b = 9.362 (1) Å

c = 10.7258 (10) Å

α = 69.765 (8)°

β = 66.733 (8)°

γ = 70.605 (8)°

V = 761.08 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.35 × 0.32 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

8164 measured reflections

3995 independent reflections

3410 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.194

S = 1.09

3995 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018625/hk2681sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018625/hk2681Isup2.hkl

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

C19H17NO2	Z = 2
Mr = 291.34	F(000) = 308
Triclinic, P1	Dx = 1.271 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0282 (10) Å	Cell parameters from 1548 reflections
b = 9.362 (1) Å	θ = 2.4–29.2°
c = 10.7258 (10) Å	µ = 0.08 mm−1
α = 69.765 (8)°	T = 120 K
β = 66.733 (8)°	Block, colourless
γ = 70.605 (8)°	0.35 × 0.32 × 0.25 mm
V = 761.08 (15) Å3

Bruker SMART CCD area-detector diffractometer	Rint = 0.044
φ and ω scans	θmax = 29.2°, θmin = 2.4°
8164 measured reflections	h = −12→12
3995 independent reflections	k = −12→12
3410 reflections with I > 2σ(I)	l = −13→14

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.065	w = 1/[σ2(Fo2) + (0.0955P)2 + 0.1587P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.194	(Δ/σ)max = 0.01
S = 1.09	Δρmax = 0.33 e Å−3
3995 reflections	Δρmin = −0.35 e Å−3
199 parameters

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
O1	0.6903 (3)	−0.70878 (17)	0.11893 (14)	0.0879 (5)
O2	0.6965 (2)	−0.95151 (14)	0.24871 (13)	0.0696 (4)
N1	0.44256 (15)	−0.71135 (15)	0.57975 (13)	0.0470 (3)
C1	0.56342 (18)	−0.68228 (16)	0.60840 (15)	0.0438 (3)
C2	0.5192 (2)	−0.6418 (2)	0.73600 (17)	0.0551 (4)
H2	0.4104	−0.6328	0.7953	0.066*
C3	0.6347 (3)	−0.6159 (2)	0.77284 (19)	0.0622 (5)
H3	0.6046	−0.5907	0.8575	0.075*
C4	0.7988 (2)	−0.6273 (2)	0.6834 (2)	0.0615 (4)
H4	0.8767	−0.6096	0.7094	0.074*
C5	0.8456 (2)	−0.66413 (19)	0.55808 (18)	0.0523 (4)
H5	0.9545	−0.6702	0.4994	0.063*
C6	0.72854 (17)	−0.69295 (15)	0.51769 (15)	0.0420 (3)
C7	0.76870 (17)	−0.73393 (15)	0.38991 (14)	0.0402 (3)
C8	0.94211 (17)	−0.75008 (16)	0.29187 (15)	0.0423 (3)
C9	1.0023 (2)	−0.61966 (19)	0.20110 (18)	0.0546 (4)
H9	0.9326	−0.5206	0.1985	0.066*
C10	1.1658 (2)	−0.6361 (2)	0.11427 (19)	0.0619 (4)
H10	1.2049	−0.5483	0.0535	0.074*
C11	1.2697 (2)	−0.7819 (2)	0.11829 (18)	0.0612 (5)
H11	1.3796	−0.7925	0.0614	0.073*
C12	1.2116 (2)	−0.9125 (2)	0.20633 (19)	0.0622 (4)
H12	1.2818	−1.0112	0.2081	0.075*
C13	1.0480 (2)	−0.89658 (18)	0.29248 (17)	0.0526 (4)
H13	1.009	−0.9851	0.3512	0.063*
C14	0.64476 (17)	−0.76184 (16)	0.36344 (14)	0.0410 (3)
C15	0.67936 (18)	−0.80112 (17)	0.22859 (15)	0.0451 (3)
C16	0.7336 (3)	−1.0130 (2)	0.12943 (19)	0.0640 (5)
H16A	0.7594	−0.9331	0.0428	0.077*
H16B	0.6389	−1.0461	0.1365	0.077*
C17	0.8780 (3)	−1.1482 (3)	0.1307 (2)	0.0694 (5)
H17A	0.8511	−1.2265	0.2168	0.083*
H17B	0.9711	−1.114	0.1231	0.083*
H17C	0.905	−1.1913	0.0532	0.083*
C18	0.48148 (18)	−0.75086 (17)	0.46289 (15)	0.0441 (3)
C19	0.3470 (2)	−0.7867 (2)	0.43737 (19)	0.0577 (4)
H19A	0.2567	−0.6965	0.4356	0.069*
H19B	0.3086	−0.8727	0.511	0.069*
H19C	0.3897	−0.8138	0.3491	0.069*

	U11	U22	U33	U12	U13	U23
O1	0.1583 (17)	0.0598 (8)	0.0463 (7)	−0.0329 (9)	−0.0344 (9)	−0.0036 (6)
O2	0.1184 (12)	0.0481 (6)	0.0487 (6)	−0.0242 (7)	−0.0284 (7)	−0.0121 (5)
N1	0.0443 (6)	0.0499 (7)	0.0454 (6)	−0.0124 (5)	−0.0135 (5)	−0.0091 (5)
C1	0.0471 (7)	0.0398 (6)	0.0437 (7)	−0.0072 (5)	−0.0161 (6)	−0.0096 (5)
C2	0.0607 (9)	0.0556 (9)	0.0460 (8)	−0.0086 (7)	−0.0143 (7)	−0.0166 (6)
C3	0.0786 (12)	0.0623 (10)	0.0558 (9)	−0.0085 (8)	−0.0288 (9)	−0.0248 (8)
C4	0.0684 (11)	0.0631 (10)	0.0709 (11)	−0.0092 (8)	−0.0375 (9)	−0.0251 (8)
C5	0.0494 (8)	0.0540 (8)	0.0629 (9)	−0.0071 (6)	−0.0261 (7)	−0.0203 (7)
C6	0.0437 (7)	0.0376 (6)	0.0472 (7)	−0.0052 (5)	−0.0191 (6)	−0.0117 (5)
C7	0.0408 (6)	0.0364 (6)	0.0433 (7)	−0.0082 (5)	−0.0146 (5)	−0.0087 (5)
C8	0.0411 (6)	0.0440 (7)	0.0442 (7)	−0.0097 (5)	−0.0151 (5)	−0.0119 (5)
C9	0.0563 (9)	0.0464 (8)	0.0594 (9)	−0.0154 (6)	−0.0170 (7)	−0.0090 (6)
C10	0.0627 (10)	0.0744 (11)	0.0509 (9)	−0.0347 (9)	−0.0119 (7)	−0.0071 (8)
C11	0.0454 (8)	0.0894 (13)	0.0472 (8)	−0.0166 (8)	−0.0103 (6)	−0.0190 (8)
C12	0.0497 (9)	0.0676 (10)	0.0589 (9)	0.0023 (7)	−0.0163 (7)	−0.0192 (8)
C13	0.0499 (8)	0.0455 (7)	0.0544 (8)	−0.0070 (6)	−0.0147 (6)	−0.0086 (6)
C14	0.0442 (7)	0.0394 (6)	0.0405 (6)	−0.0110 (5)	−0.0151 (5)	−0.0075 (5)
C15	0.0476 (7)	0.0471 (7)	0.0435 (7)	−0.0142 (6)	−0.0163 (6)	−0.0089 (5)
C16	0.0854 (13)	0.0621 (10)	0.0558 (9)	−0.0166 (9)	−0.0259 (9)	−0.0238 (8)
C17	0.0650 (11)	0.0801 (13)	0.0642 (11)	−0.0162 (9)	−0.0143 (9)	−0.0266 (9)
C18	0.0433 (7)	0.0452 (7)	0.0439 (7)	−0.0124 (5)	−0.0162 (5)	−0.0060 (5)
C19	0.0497 (8)	0.0728 (11)	0.0576 (9)	−0.0221 (8)	−0.0213 (7)	−0.0115 (8)

C1—N1	1.3708 (19)	C11—H11	0.93
C1—C6	1.415 (2)	C12—C13	1.388 (2)
C1—C2	1.415 (2)	C12—H12	0.93
C2—C3	1.365 (3)	C13—H13	0.93
C2—H2	0.93	C14—C18	1.433 (2)
C3—C4	1.403 (3)	C14—C15	1.5031 (19)
C3—H3	0.93	C15—O1	1.1841 (19)
C4—C5	1.371 (2)	C15—O2	1.3132 (19)
C4—H4	0.93	C16—O2	1.457 (2)
C5—C6	1.417 (2)	C16—C17	1.485 (3)
C5—H5	0.93	C16—H16A	0.97
C6—C7	1.4268 (19)	C16—H16B	0.97
C7—C14	1.3775 (19)	C17—H17A	0.96
C7—C8	1.4939 (19)	C17—H17B	0.96
C8—C13	1.387 (2)	C17—H17C	0.96
C8—C9	1.391 (2)	C18—N1	1.311 (2)
C9—C10	1.390 (2)	C18—C19	1.503 (2)
C9—H9	0.93	C19—H19A	0.96
C10—C11	1.373 (3)	C19—H19B	0.96
C10—H10	0.93	C19—H19C	0.96
C11—C12	1.378 (3)
N1—C1—C6	123.08 (13)	C11—C12—H12	120
N1—C1—C2	117.62 (14)	C13—C12—H12	120
C6—C1—C2	119.30 (14)	C8—C13—C12	120.70 (15)
C3—C2—C1	120.59 (16)	C8—C13—H13	119.7
C3—C2—H2	119.7	C12—C13—H13	119.7
C1—C2—H2	119.7	C7—C14—C18	120.33 (13)
C2—C3—C4	120.20 (16)	C7—C14—C15	120.08 (12)
C2—C3—H3	119.9	C18—C14—C15	119.58 (12)
C4—C3—H3	119.9	O1—C15—O2	124.63 (15)
C5—C4—C3	120.81 (15)	O1—C15—C14	124.46 (14)
C5—C4—H4	119.6	O2—C15—C14	110.91 (12)
C3—C4—H4	119.6	O2—C16—C17	107.69 (15)
C4—C5—C6	120.21 (16)	O2—C16—H16A	110.2
C4—C5—H5	119.9	C17—C16—H16A	110.2
C6—C5—H5	119.9	O2—C16—H16B	110.2
C1—C6—C5	118.89 (13)	C17—C16—H16B	110.2
C1—C6—C7	117.77 (12)	H16A—C16—H16B	108.5
C5—C6—C7	123.35 (13)	C16—C17—H17A	109.5
C14—C7—C6	117.96 (12)	C16—C17—H17B	109.5
C14—C7—C8	122.12 (12)	H17A—C17—H17B	109.5
C6—C7—C8	119.89 (12)	C16—C17—H17C	109.5
C13—C8—C9	118.59 (14)	H17A—C17—H17C	109.5
C13—C8—C7	120.19 (13)	H17B—C17—H17C	109.5
C9—C8—C7	121.21 (13)	N1—C18—C14	122.27 (13)
C10—C9—C8	120.56 (16)	N1—C18—C19	117.00 (14)
C10—C9—H9	119.7	C14—C18—C19	120.73 (13)
C8—C9—H9	119.7	C18—C19—H19A	109.5
C11—C10—C9	120.00 (16)	C18—C19—H19B	109.5
C11—C10—H10	120	H19A—C19—H19B	109.5
C9—C10—H10	120	C18—C19—H19C	109.5
C10—C11—C12	120.20 (16)	H19A—C19—H19C	109.5
C10—C11—H11	119.9	H19B—C19—H19C	109.5
C12—C11—H11	119.9	C18—N1—C1	118.58 (13)
C11—C12—C13	119.94 (16)	C15—O2—C16	119.11 (13)
N1—C1—C2—C3	178.06 (15)	C10—C11—C12—C13	−0.8 (3)
C6—C1—C2—C3	−1.1 (2)	C9—C8—C13—C12	1.3 (2)
C1—C2—C3—C4	0.8 (3)	C7—C8—C13—C12	−177.08 (15)
C2—C3—C4—C5	0.1 (3)	C11—C12—C13—C8	−0.5 (3)
C3—C4—C5—C6	−0.6 (3)	C6—C7—C14—C18	−0.5 (2)
N1—C1—C6—C5	−178.56 (13)	C8—C7—C14—C18	177.58 (12)
C2—C1—C6—C5	0.6 (2)	C6—C7—C14—C15	178.33 (11)
N1—C1—C6—C7	0.9 (2)	C8—C7—C14—C15	−3.6 (2)
C2—C1—C6—C7	−179.97 (12)	C7—C14—C15—O1	−76.8 (2)
C4—C5—C6—C1	0.3 (2)	C18—C14—C15—O1	102.0 (2)
C4—C5—C6—C7	−179.12 (14)	C7—C14—C15—O2	102.89 (16)
C1—C6—C7—C14	−0.56 (19)	C18—C14—C15—O2	−78.24 (17)
C5—C6—C7—C14	178.85 (13)	C7—C14—C18—N1	1.5 (2)
C1—C6—C7—C8	−178.70 (12)	C15—C14—C18—N1	−177.41 (13)
C5—C6—C7—C8	0.7 (2)	C7—C14—C18—C19	−177.80 (14)
C14—C7—C8—C13	−79.78 (18)	C15—C14—C18—C19	3.3 (2)
C6—C7—C8—C13	98.29 (17)	C14—C18—N1—C1	−1.1 (2)
C14—C7—C8—C9	101.92 (17)	C19—C18—N1—C1	178.13 (13)
C6—C7—C8—C9	−80.01 (18)	C6—C1—N1—C18	0.0 (2)
C13—C8—C9—C10	−0.8 (2)	C2—C1—N1—C18	−179.18 (13)
C7—C8—C9—C10	177.53 (15)	O1—C15—O2—C16	0.8 (3)
C8—C9—C10—C11	−0.4 (3)	C14—C15—O2—C16	−178.93 (15)
C9—C10—C11—C12	1.2 (3)	C17—C16—O2—C15	129.54 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O1	0.97	2.32	2.711 (3)	103
C19—H19B···O2i	0.96	2.52	3.374 (3)	147
C19—H19C···O2	0.96	2.59	3.212 (3)	122
C12—H12···Cg2ii	0.93	2.95	3.750 (3)	145
C17—H17C···Cg3iii	0.96	2.97	3.883 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O1	0.97	2.32	2.711 (3)	103
C19—H19B⋯O2i	0.96	2.52	3.374 (3)	147
C19—H19C⋯O2	0.96	2.59	3.212 (3)	122
C12—H12⋯Cg2ii	0.93	2.95	3.750 (3)	145
C17—H17C⋯Cg3iii	0.96	2.97	3.883 (3)	160

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 and Cg3 are the centroids of rings C1–C6 and C8–C13, respectively.