2-Isopropyl-5-methyl­cyclo­hexyl quinoline-2-carboxyl­ate

Fazal, E.; Jasinski, J.P.; Anderson, B.J.; Sudha, B.S.; Nagarajan, S.

doi:10.1107/S1600536813033060

organic compounds

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ISSN: 2056-9890

Volume 70| Part 1| January 2014| Pages o35-o36

https://doi.org/10.1107/S1600536813033060

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2-Isopropyl-5-methylcyclohexyl quinoline-2-carboxylate

E. Fazal,^a Jerry P. Jasinski,^b ^* Brian J. Anderson,^b B. S. Sudha ^a and S. Nagarajan ^c

^aDepartment of Chemistry, Yuvaraja's College, Mysore 570 005, India, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^cP.P.S.F.T. Department, Central Food Technplogy Research institute, Mysore 570 005, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 6 December 2013; accepted 6 December 2013; online 11 December 2013)

In the title compound, C₂₀H₂₅NO₂, the cyclohexyl ring adopts a slightly disordered chair conformation. The dihedral angle between the mean planes of the quinoline ring and the carboxylate group is 22.2 (6)°. In the crystal, weak C—H⋯N interactions make chains along [010].

CCDC reference: 975532

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_r = 311.41
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.098
S = 1.04
3389 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ); 1372 Friedel pairs
Absolute structure parameter: −0.01 (13)

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

CCDC reference: 975532

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033060/tk5278sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033060/tk5278Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813033060/tk5278Isup3.cml

checkCIF report

Comment top

Quinoline-2 carboxylic acid derivatives are a class of important materials as anti-tuberculosis agents, as fluorescent reagents, hydrophobic field-detection reagents, visualisation reagents, fluorescent labelled peptide probes and as antihyperglycemics. Quinoline derivatives represent a major class of heterocycles and are found in natural products (Morimoto et al., 1991; Michael, 1997), numerous commercial products, including fragrances, dyes (Padwa et al., 1999) and biologically active compounds (Markees et al., 1970; Campbell et al., 1988). Quinoline alkaloids such as quinine, chloroquin, mefloquine and amodiaquine are used as efficient drugs for the treatment of malaria (Robert & Meunier, 1998). Quinoline as a privileged scaffold in cancer drug discovery is published (Solomon & Lee, 2011). The crystal structures of 4-methylphenyl quinoline-2-carboxylate (Fazal et al., 2012), 4-chloro-3-methylphenyl quinoline-2- carboxylate (Fazal et al., 2013a), 4-chlorophenyl quinoline- 2-carboxylate (Fazal et al., 2013b), 3,4-dimethylphenyl quinoline-2-carboxylate (Fazal et al., 2013c), 1-(quinolin-2-yl)ethanone (Butcher et al., 2007) and methyl quinoline-2-carboxylate (Jing & Qin, 2008) as well as the synthesis, crystal structures and theoretical studies of four Schiff bases derived from 4-hydrazinyl-8-(trifluoromethyl) quinoline (Jasinski et al., 2010) have been reported. In view of the importance of quinolines, this paper reports the crystal structure of the title compound, (I), C₂₀H₂₅NO₂.

In the title compound, (I), Fig. 1, the cyclohexyl ring adopts a slightly disordered chair conformation (puckering parameters for C11–C16: Q, θ, and φ = 0.593 (2)Å, 4.32 (19)° and 308 (2)°, respectively (Cremer & Pople, 1975). The dihedral angle between the mean planes of the quinoline ring and the carboxylate group (C2/C1/O1/O2) is 22.2 (6)°. In the crystal, weak C7—H7···N1 intermolecular interactions make chains along [0 1 0] and influence the crystal packing (Fig. 2 & Table 1).

Related literature top

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 top

The title compound was prepared by the following procedure: To a mixture of 1.73 g (10 mmol) of quinaldic acid and 1.56 g (10 mmole) of 2-isopropyl-5-methylcyclohexanol in a round-bottomed flask fitted with a reflux condenser with a drying tube is added phosphorous oxychloride (0.150 g, 10 mmol). The mixture is heated with occasional swirling, and temperature is maintained at 348-353 K. At the end of 8 h the reaction mixture is poured in to a solution of sodium bicarbonate (2 g) in water (25 mL). The precipitated ester is collected on a filter and washed with water. The yield of crude, air dried 2-isopropyl-5-methylcyclohexyl quinoline-2-carboxylate is isolated in 1.71 to 1.85 g (65-70 %) yield. X-ray quality crystals were obtained by recrystallization from absolute ethanol by slow evaporation (M.pt: 414-416 K).

Structure description top

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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); 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 (Dolomanov et al., 2009).

Figures top

	Fig. 1. ORTEP drawing of (I) showing the labeling scheme with 50% probability displacement ellipsoids.
	Fig. 2. Molecular packing for (I) viewed along the a axis. Dashed lines indicate weak C7—H7···N1 intermolecular interactions making chains along [0 1 0]. The remaining H atoms have been removed for clarity.

2-Isopropyl-5-methylcyclohexyl quinoline-2-carboxylate top

Crystal data top

C₂₀H₂₅NO₂	D_x = 1.198 Mg m⁻³
M_r = 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

Data collection top

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	R_int = 0.037
ω scans	θ_max = 72.4°, θ_min = 4.7°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012).	h = −11→5
T_min = 0.921, T_max = 1.000	k = −14→14
11010 measured reflections	l = −19→18

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0661P)² + 0.1484P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.037	(Δ/σ)_max < 0.001
wR(F²) = 0.098	Δρ_max = 0.20 e Å⁻³
S = 1.04	Δρ_min = −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

Crystal data top

C₂₀H₂₅NO₂	V = 1726.47 (6) Å³
M_r = 311.41	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 9.31412 (17) Å	µ = 0.60 mm⁻¹
b = 11.9669 (2) Å	T = 173 K
c = 15.4894 (3) Å	0.38 × 0.32 × 0.24 mm

Data collection top

Agilent Gemini EOS diffractometer	3389 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012).	3281 reflections with I > 2σ(I)
T_min = 0.921, T_max = 1.000	R_int = 0.037
11010 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.098	Δρ_max = 0.20 e Å⁻³
S = 1.04	Δρ_min = −0.17 e Å⁻³
3389 reflections	Absolute structure: Flack (1983); 1372 Friedel pairs
212 parameters	Absolute structure parameter: −0.01 (13)
0 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2.

Acknowledgements

EF thanks CFTRI, Mysore, and Yuvaraja's College, UOM, for providing research facilities, and is grateful to Mr J. R. Manjunatha, PPSFT, CFTRI, for recording NMR spectra. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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