2-Isopropyl-5-methyl-cyclo-hexyl quinoline-2-carboxyl-ate.

In the title compound, C20H25NO2, the cyclo-hexyl ring adopts a slightly disordered chair conformation. The dihedral angle between the mean planes of the quinoline ring and the carboxyl-ate group is 22.2 (6)°. In the crystal, weak C-H⋯N inter-actions make chains along [010].

Related literature

For heterocycles in natural products, see: Morimoto et al. (1991 ▶); Michael (1997 ▶). For heterocycles in fragrances and dyes, see: Padwa et al. (1999 ▶). For heterocycles in biologically active compounds, see: Markees et al. (1970 ▶); Campbell et al.(1988 ▶). For quinoline alkaloids used as efficient drugs for the treatment of malaria, see: Robert & Meunier, (1998 ▶). For quinoline as a privileged scaffold in cancer drug discovery, see: Solomon & Lee (2011 ▶). For related structures, see: Fazal et al. (2012 ▶, 2013a ▶,b ▶,c ▶); Butcher et al. (2007 ▶); Jing & Qin (2008 ▶); Jasinski et al. (2010 ▶). For puckering parameters, see Cremer & Pople (1975 ▶).

Experimental

Crystal data

C20H25NO2

M = 311.41

Orthorhombic,

a = 9.31412 (17) Å

b = 11.9669 (2) Å

c = 15.4894 (3) Å

V = 1726.47 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.60 mm−1

T = 173 K

0.38 × 0.32 × 0.24 mm

Data collection

Agilent Gemini EOS diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶). T min = 0.921, T max = 1.000

11010 measured reflections

3389 independent reflections

3281 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.04

3389 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶); 1372 Friedel pairs

Absolute structure parameter: −0.01 (13)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813033060/tk5278sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033060/tk5278Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033060/tk5278Isup3.cml

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

C20H25NO2	Dx = 1.198 Mg m−3
Mr = 311.41	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 6294 reflections
a = 9.31412 (17) Å	θ = 4.7–72.3°
b = 11.9669 (2) Å	µ = 0.60 mm−1
c = 15.4894 (3) Å	T = 173 K
V = 1726.47 (6) Å3	Irregular, colourless
Z = 4	0.38 × 0.32 × 0.24 mm
F(000) = 672

Agilent Gemini EOS diffractometer	3389 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3281 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.037
ω scans	θmax = 72.4°, θmin = 4.7°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012).	h = −11→5
Tmin = 0.921, Tmax = 1.000	k = −14→14
11010 measured reflections	l = −19→18

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0661P)2 + 0.1484P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.037	(Δ/σ)max < 0.001
wR(F2) = 0.098	Δρmax = 0.20 e Å−3
S = 1.04	Δρmin = −0.17 e Å−3
3389 reflections	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
212 parameters	Extinction coefficient: 0.0093 (10)
0 restraints	Absolute structure: Flack (1983); 1372 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (13)
Hydrogen site location: inferred from neighbouring sites

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	0.92164 (17)	0.54532 (12)	0.51535 (10)	0.0408 (4)
O2	0.79892 (13)	0.64179 (10)	0.41465 (8)	0.0261 (3)
N1	0.70130 (16)	0.45417 (11)	0.34655 (9)	0.0230 (3)
C1	0.83460 (19)	0.55000 (15)	0.45755 (11)	0.0253 (4)
C2	0.75365 (19)	0.44942 (14)	0.42566 (11)	0.0240 (4)
C3	0.7426 (2)	0.35518 (16)	0.48000 (11)	0.0295 (4)
H3	0.7848	0.3554	0.5358	0.035*
C4	0.6697 (2)	0.26358 (15)	0.45059 (12)	0.0311 (4)
H4	0.6592	0.1997	0.4864	0.037*
C5	0.6104 (2)	0.26440 (14)	0.36683 (12)	0.0262 (4)
C6	0.5318 (2)	0.17400 (15)	0.33109 (14)	0.0327 (4)
H6	0.5171	0.1083	0.3643	0.039*
C7	0.4772 (2)	0.18048 (17)	0.24958 (15)	0.0348 (4)
H7	0.4233	0.1199	0.2268	0.042*
C8	0.5004 (2)	0.27692 (16)	0.19885 (13)	0.0314 (4)
H8	0.4633	0.2800	0.1418	0.038*
C9	0.5755 (2)	0.36578 (15)	0.23068 (12)	0.0283 (4)
H9	0.5908	0.4299	0.1957	0.034*
C10	0.63087 (19)	0.36241 (14)	0.31610 (11)	0.0235 (4)
C11	0.88592 (18)	0.74196 (14)	0.42860 (11)	0.0243 (4)
H11	0.9840	0.7195	0.4483	0.029*
C12	0.8164 (2)	0.81503 (14)	0.49708 (12)	0.0265 (4)
H12A	0.8105	0.7732	0.5521	0.032*
H12B	0.7174	0.8342	0.4790	0.032*
C13	0.9028 (2)	0.92258 (15)	0.51090 (12)	0.0290 (4)
H13	0.9993	0.9015	0.5340	0.035*
C14	0.9247 (2)	0.98221 (15)	0.42454 (14)	0.0345 (5)
H14A	0.8310	1.0098	0.4033	0.041*
H14B	0.9880	1.0477	0.4334	0.041*
C15	0.9910 (2)	0.90594 (16)	0.35660 (13)	0.0329 (4)
H15A	1.0879	0.8826	0.3756	0.039*
H15B	1.0012	0.9474	0.3016	0.039*
C16	0.89728 (19)	0.80190 (15)	0.34186 (12)	0.0259 (4)
H16	0.7988	0.8290	0.3269	0.031*
C17	0.9465 (2)	0.72518 (16)	0.26757 (12)	0.0301 (4)
H17	0.8757	0.6626	0.2637	0.036*
C18	1.0935 (2)	0.67304 (19)	0.28311 (15)	0.0397 (5)
H18A	1.1647	0.7323	0.2919	0.060*
H18B	1.1208	0.6280	0.2329	0.060*
H18C	1.0896	0.6253	0.3345	0.060*
C19	0.9430 (3)	0.7870 (2)	0.18104 (14)	0.0469 (6)
H19A	0.8472	0.8188	0.1719	0.070*
H19B	0.9652	0.7347	0.1343	0.070*
H19C	1.0143	0.8472	0.1816	0.070*
C20	0.8303 (2)	0.99877 (17)	0.57671 (14)	0.0370 (5)
H20A	0.7301	1.0109	0.5600	0.056*
H20B	0.8806	1.0706	0.5786	0.056*
H20C	0.8337	0.9637	0.6338	0.056*

	U11	U22	U33	U12	U13	U23
O1	0.0551 (9)	0.0303 (7)	0.0368 (8)	−0.0097 (7)	−0.0205 (7)	0.0059 (6)
O2	0.0273 (6)	0.0196 (6)	0.0312 (6)	−0.0035 (5)	−0.0044 (5)	0.0018 (5)
N1	0.0272 (7)	0.0183 (6)	0.0235 (7)	0.0013 (6)	−0.0003 (6)	0.0007 (5)
C1	0.0306 (8)	0.0225 (8)	0.0228 (8)	−0.0003 (7)	0.0004 (7)	0.0008 (7)
C2	0.0267 (8)	0.0217 (8)	0.0237 (8)	0.0019 (7)	0.0013 (7)	−0.0004 (7)
C3	0.0405 (10)	0.0248 (8)	0.0232 (8)	−0.0003 (8)	−0.0017 (7)	0.0021 (7)
C4	0.0448 (10)	0.0211 (8)	0.0273 (9)	−0.0001 (7)	0.0038 (8)	0.0053 (7)
C5	0.0297 (8)	0.0194 (8)	0.0294 (9)	0.0005 (7)	0.0053 (7)	−0.0012 (7)
C6	0.0376 (10)	0.0214 (8)	0.0393 (11)	−0.0050 (7)	0.0048 (8)	−0.0029 (7)
C7	0.0328 (10)	0.0288 (9)	0.0428 (11)	−0.0054 (8)	−0.0005 (9)	−0.0104 (8)
C8	0.0302 (9)	0.0325 (9)	0.0316 (9)	0.0036 (8)	−0.0051 (8)	−0.0078 (8)
C9	0.0306 (9)	0.0252 (9)	0.0291 (9)	0.0040 (7)	−0.0020 (7)	−0.0011 (7)
C10	0.0255 (8)	0.0198 (8)	0.0252 (8)	0.0031 (7)	0.0020 (6)	−0.0012 (6)
C11	0.0242 (7)	0.0205 (8)	0.0281 (8)	−0.0043 (7)	−0.0026 (6)	0.0017 (7)
C12	0.0289 (9)	0.0229 (8)	0.0279 (8)	−0.0052 (7)	−0.0006 (7)	0.0008 (7)
C13	0.0316 (8)	0.0241 (9)	0.0314 (9)	−0.0045 (7)	−0.0045 (7)	−0.0022 (7)
C14	0.0427 (11)	0.0218 (8)	0.0389 (11)	−0.0087 (8)	0.0009 (8)	0.0010 (8)
C15	0.0386 (10)	0.0253 (9)	0.0348 (10)	−0.0102 (8)	0.0036 (8)	0.0030 (8)
C16	0.0269 (8)	0.0235 (8)	0.0273 (9)	−0.0033 (7)	−0.0013 (7)	0.0025 (7)
C17	0.0331 (9)	0.0310 (9)	0.0263 (9)	−0.0042 (8)	−0.0006 (7)	−0.0004 (8)
C18	0.0362 (11)	0.0439 (12)	0.0389 (11)	0.0035 (9)	0.0041 (9)	−0.0063 (9)
C19	0.0619 (14)	0.0501 (13)	0.0286 (11)	−0.0001 (12)	0.0011 (10)	0.0018 (9)
C20	0.0443 (11)	0.0285 (10)	0.0382 (10)	−0.0051 (8)	−0.0013 (9)	−0.0066 (8)

O1—C1	1.209 (2)	C12—H12B	0.9900
O2—C1	1.326 (2)	C12—C13	1.533 (2)
O2—C11	1.4630 (19)	C13—H13	1.0000
N1—C2	1.320 (2)	C13—C14	1.530 (3)
N1—C10	1.363 (2)	C13—C20	1.525 (3)
C1—C2	1.504 (2)	C14—H14A	0.9900
C2—C3	1.411 (2)	C14—H14B	0.9900
C3—H3	0.9500	C14—C15	1.524 (3)
C3—C4	1.367 (3)	C15—H15A	0.9900
C4—H4	0.9500	C15—H15B	0.9900
C4—C5	1.410 (3)	C15—C16	1.537 (2)
C5—C6	1.419 (3)	C16—H16	1.0000
C5—C10	1.425 (2)	C16—C17	1.542 (3)
C6—H6	0.9500	C17—H17	1.0000
C6—C7	1.363 (3)	C17—C18	1.524 (3)
C7—H7	0.9500	C17—C19	1.531 (3)
C7—C8	1.413 (3)	C18—H18A	0.9800
C8—H8	0.9500	C18—H18B	0.9800
C8—C9	1.365 (3)	C18—H18C	0.9800
C9—H9	0.9500	C19—H19A	0.9800
C9—C10	1.420 (2)	C19—H19B	0.9800
C11—H11	1.0000	C19—H19C	0.9800
C11—C12	1.520 (2)	C20—H20A	0.9800
C11—C16	1.527 (2)	C20—H20B	0.9800
C12—H12A	0.9900	C20—H20C	0.9800
C1—O2—C11	117.76 (13)	C14—C13—H13	108.1
C2—N1—C10	117.66 (15)	C20—C13—C12	111.29 (16)
O1—C1—O2	125.27 (16)	C20—C13—H13	108.1
O1—C1—C2	122.85 (16)	C20—C13—C14	111.39 (16)
O2—C1—C2	111.88 (14)	C13—C14—H14A	109.2
N1—C2—C1	117.11 (15)	C13—C14—H14B	109.2
N1—C2—C3	124.13 (16)	H14A—C14—H14B	107.9
C3—C2—C1	118.72 (15)	C15—C14—C13	112.25 (16)
C2—C3—H3	120.7	C15—C14—H14A	109.2
C4—C3—C2	118.59 (16)	C15—C14—H14B	109.2
C4—C3—H3	120.7	C14—C15—H15A	109.4
C3—C4—H4	120.2	C14—C15—H15B	109.4
C3—C4—C5	119.69 (16)	C14—C15—C16	110.97 (16)
C5—C4—H4	120.2	H15A—C15—H15B	108.0
C4—C5—C6	123.76 (17)	C16—C15—H15A	109.4
C4—C5—C10	117.45 (16)	C16—C15—H15B	109.4
C6—C5—C10	118.79 (17)	C11—C16—C15	106.80 (14)
C5—C6—H6	119.7	C11—C16—H16	107.0
C7—C6—C5	120.70 (18)	C11—C16—C17	113.43 (15)
C7—C6—H6	119.7	C15—C16—H16	107.0
C6—C7—H7	119.9	C15—C16—C17	115.11 (15)
C6—C7—C8	120.29 (18)	C17—C16—H16	107.0
C8—C7—H7	119.9	C16—C17—H17	107.2
C7—C8—H8	119.5	C18—C17—C16	113.14 (16)
C9—C8—C7	120.93 (18)	C18—C17—H17	107.2
C9—C8—H8	119.5	C18—C17—C19	110.80 (18)
C8—C9—H9	120.0	C19—C17—C16	111.05 (17)
C8—C9—C10	120.01 (18)	C19—C17—H17	107.2
C10—C9—H9	120.0	C17—C18—H18A	109.5
N1—C10—C5	122.45 (15)	C17—C18—H18B	109.5
N1—C10—C9	118.30 (16)	C17—C18—H18C	109.5
C9—C10—C5	119.25 (16)	H18A—C18—H18B	109.5
O2—C11—H11	109.3	H18A—C18—H18C	109.5
O2—C11—C12	109.78 (14)	H18B—C18—H18C	109.5
O2—C11—C16	107.05 (14)	C17—C19—H19A	109.5
C12—C11—H11	109.3	C17—C19—H19B	109.5
C12—C11—C16	111.93 (14)	C17—C19—H19C	109.5
C16—C11—H11	109.3	H19A—C19—H19B	109.5
C11—C12—H12A	109.5	H19A—C19—H19C	109.5
C11—C12—H12B	109.5	H19B—C19—H19C	109.5
C11—C12—C13	110.90 (15)	C13—C20—H20A	109.5
H12A—C12—H12B	108.0	C13—C20—H20B	109.5
C13—C12—H12A	109.5	C13—C20—H20C	109.5
C13—C12—H12B	109.5	H20A—C20—H20B	109.5
C12—C13—H13	108.1	H20A—C20—H20C	109.5
C14—C13—C12	109.86 (15)	H20B—C20—H20C	109.5
O1—C1—C2—N1	−157.29 (18)	C7—C8—C9—C10	−0.4 (3)
O1—C1—C2—C3	20.5 (3)	C8—C9—C10—N1	−177.92 (16)
O2—C1—C2—N1	22.5 (2)	C8—C9—C10—C5	1.7 (3)
O2—C1—C2—C3	−159.75 (16)	C10—N1—C2—C1	178.36 (15)
O2—C11—C12—C13	−178.14 (13)	C10—N1—C2—C3	0.7 (2)
O2—C11—C16—C15	−179.03 (13)	C10—C5—C6—C7	0.3 (3)
O2—C11—C16—C17	−51.15 (19)	C11—O2—C1—O1	9.8 (3)
N1—C2—C3—C4	−1.9 (3)	C11—O2—C1—C2	−169.94 (14)
C1—O2—C11—C12	−95.24 (17)	C11—C12—C13—C14	53.7 (2)
C1—O2—C11—C16	143.06 (15)	C11—C12—C13—C20	177.55 (16)
C1—C2—C3—C4	−179.55 (17)	C11—C16—C17—C18	−59.7 (2)
C2—N1—C10—C5	1.1 (2)	C11—C16—C17—C19	174.94 (17)
C2—N1—C10—C9	−179.21 (16)	C12—C11—C16—C15	60.63 (18)
C2—C3—C4—C5	1.3 (3)	C12—C11—C16—C17	−171.49 (14)
C3—C4—C5—C6	−179.24 (18)	C12—C13—C14—C15	−53.7 (2)
C3—C4—C5—C10	0.4 (3)	C13—C14—C15—C16	57.9 (2)
C4—C5—C6—C7	179.92 (19)	C14—C15—C16—C11	−59.2 (2)
C4—C5—C10—N1	−1.7 (3)	C14—C15—C16—C17	173.92 (16)
C4—C5—C10—C9	178.65 (17)	C15—C16—C17—C18	63.7 (2)
C5—C6—C7—C8	1.1 (3)	C15—C16—C17—C19	−61.6 (2)
C6—C5—C10—N1	177.98 (16)	C16—C11—C12—C13	−59.40 (19)
C6—C5—C10—C9	−1.7 (2)	C20—C13—C14—C15	−177.47 (17)
C6—C7—C8—C9	−1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N1i	0.95	2.56	3.509 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N1i	0.95	2.56	3.509 (2)	174

Symmetry code: (i) .