Ethyl 2,7,7-trimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate

Kurbanova, M.M.; Huseynov, E.Z.; Gurbanov, A.V.; Maharramov, A.M.; Ng, S.W.

doi:10.1107/S1600536812028371

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2233

https://doi.org/10.1107/S1600536812028371

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Ethyl 2,7,7-trimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Malahat M. Kurbanova,^a Elnur Z. Huseynov,^a Atash V. Gurbanov,^a Abel M. Maharramov ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 21 June 2012; accepted 22 June 2012; online 27 June 2012)

In the title compound, C₂₁H₂₅NO₃, the hydropyridine ring that constitutes a part of the hexahydroquinoline fused-ring system adopts a sofa conformation; the methine C atom deviates from the least-squares plane defined by the remaining five non-H atoms (r.m.s. deviation = 0.088 Å) by 0.454 (3) Å. The phenyl ring is aligned at 85.5 (1)° with respect to this mean plane. In the crystal, adjacent molecules are linked via an N—H⋯O hydrogen bond, involving the amino group and the carbonyl O atom of the fused-ring system, forming chains running along [100]. The ethyl group is disordered over two positions in a 0.609 (6):0.391 (6) ratio.

Related literature

For the synthesis, see: Safari et al. (2011 ). For the crystal structure of methyl 2,7,7-trimethyl-4-phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, see: Duque et al. (2000 ).

Experimental

Crystal data

C₂₁H₂₅NO₃
M_r = 339.42
Triclinic, $[P \overline 1]$
a = 7.3523 (4) Å
b = 9.6349 (5) Å
c = 13.9495 (7) Å
α = 98.370 (1)°
β = 91.778 (1)°
γ = 106.291 (1)°
V = 935.70 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
10191 measured reflections
4302 independent reflections
3439 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.135
S = 1.03
4302 reflections
254 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.87 (1)	2.04 (1)	2.890 (1)	168 (2)
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812028371/xu5576sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812028371/xu5576Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812028371/xu5576Isup3.cml

checkCIF report

Comment top

C5-Unsubstituted 1,4-dihydropyridines are readily synthesized by the reaction of dimedone, acetophenone, aromatic aldehydes, and ammonium acetate in the presence of a catalytic amount of a cobalt salt under solvent-free conditions (Safari et al. 2011). The title compound (Scheme I), was synthesized by a slightly different procedure from benzaldehyde, ethyl acetoacetate and ammonium acetate and with L-glutamine as catalyst, and in ethanol medium.

The hydropyridine ring that constitutes a part of the hexahydroquinoline fused-ring system of C₂₁H₂₅NO₃ adopts a sofa conformation; the methine C atom bearing the phenyl substituent deviates from the least-squares plane defined by the N and four double-bond C atoms by 0.454 (3) Å. The phenyl ring is nearly orthogornal to this plane (Fig. 1). The amino group is hydrogen-bond donor to the carbonyl O atom of the fused-ring of another molecule; adjacent molecules are linked by an N—H···O hydrogen bond to form a chain running along the a-axis of the triclinic cell (Table 1, Fig. 2).

Related literature top

For the synthesis, see: Safari et al. (2011). For the crystal structure of methyl 2,7,7-trimethyl-4-phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, see: Duque et al. (2000).

Experimental top

Dimedone (0.56 g, 2 mmol) was stirred with benzaldehyde (0.40 ml, 2 mmol), ethyl acetoacetate (0.5 ml, 2 mmol) and ammonium acetate (0.308 g, 2 mmol) in ethanol (50 ml) for 12 h at the room temperature. A small quantity of L-glutamine (0.05 g) was added as catalyst. Recrystallization was effected by using ethanol as solvent.

Structure description top

For the synthesis, see: Safari et al. (2011). For the crystal structure of methyl 2,7,7-trimethyl-4-phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, see: Duque et al. (2000).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₃H₂₆O₄ at the 50% probability level; H atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
	Fig. 2. Hydrogen-bonded chain motif.

Ethyl 2,7,7-trimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate top

Crystal data top

C₂₁H₂₅NO₃	Z = 2
M_r = 339.42	F(000) = 364
Triclinic, P1	D_x = 1.205 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3523 (4) Å	Cell parameters from 4443 reflections
b = 9.6349 (5) Å	θ = 2.2–29.2°
c = 13.9495 (7) Å	µ = 0.08 mm⁻¹
α = 98.370 (1)°	T = 296 K
β = 91.778 (1)°	Prism, yellow
γ = 106.291 (1)°	0.20 × 0.20 × 0.20 mm
V = 935.70 (8) Å³

Data collection top

Bruker SMART APEX diffractometer	3439 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.016
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
φ and ω scans	h = −9→9
10191 measured reflections	k = −12→12
4302 independent reflections	l = −17→18

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0682P)² + 0.1935P] where P = (F_o² + 2F_c²)/3
4302 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.27 e Å⁻³
4 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₁H₂₅NO₃	γ = 106.291 (1)°
M_r = 339.42	V = 935.70 (8) Å³
Triclinic, P1	Z = 2
a = 7.3523 (4) Å	Mo Kα radiation
b = 9.6349 (5) Å	µ = 0.08 mm⁻¹
c = 13.9495 (7) Å	T = 296 K
α = 98.370 (1)°	0.20 × 0.20 × 0.20 mm
β = 91.778 (1)°

Data collection top

Bruker SMART APEX diffractometer	3439 reflections with I > 2σ(I)
10191 measured reflections	R_int = 0.016
4302 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	4 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.27 e Å⁻³
4302 reflections	Δρ_min = −0.20 e Å⁻³
254 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.25249 (12)	0.66980 (12)	0.42973 (8)	0.0499 (3)
O2	0.6353 (2)	0.34700 (15)	0.10252 (9)	0.0749 (4)
O3	0.37322 (15)	0.41542 (13)	0.12222 (8)	0.0563 (3)
N1	0.85485 (15)	0.61848 (13)	0.37295 (8)	0.0404 (3)
H1	0.9683 (15)	0.6251 (18)	0.3964 (11)	0.053 (4)*
C1	0.73337 (16)	0.66880 (13)	0.43108 (9)	0.0327 (3)
C2	0.80247 (17)	0.72215 (15)	0.53537 (9)	0.0376 (3)
H2A	0.9355	0.7777	0.5391	0.045*
H2B	0.7932	0.6383	0.5679	0.045*
C3	0.69190 (18)	0.81798 (14)	0.58871 (9)	0.0390 (3)
C4	0.48007 (18)	0.74010 (16)	0.56507 (10)	0.0407 (3)
H4A	0.4463	0.6554	0.5980	0.049*
H4B	0.4088	0.8058	0.5913	0.049*
C5	0.41906 (16)	0.69006 (13)	0.45882 (9)	0.0338 (3)
C6	0.55737 (16)	0.66029 (13)	0.39380 (9)	0.0317 (3)
C7	0.7417 (2)	0.96857 (16)	0.55736 (13)	0.0584 (4)
H7A	0.7096	0.9577	0.4889	0.088*
H7B	0.8754	1.0157	0.5711	0.088*
H7C	0.6715	1.0271	0.5924	0.088*
C8	0.7403 (3)	0.8357 (2)	0.69817 (11)	0.0626 (5)
H8A	0.8733	0.8847	0.7129	0.094*
H8B	0.7106	0.7409	0.7178	0.094*
H8C	0.6673	0.8926	0.7324	0.094*
C10	0.50411 (16)	0.61688 (14)	0.28579 (9)	0.0341 (3)
H10	0.3704	0.5585	0.2768	0.041*
C11	0.62229 (17)	0.52035 (13)	0.24136 (9)	0.0359 (3)
C12	0.79381 (18)	0.52991 (15)	0.28380 (10)	0.0387 (3)
C13	0.9302 (2)	0.4477 (2)	0.24766 (13)	0.0604 (4)
H13A	0.9613	0.4664	0.1835	0.091*
H13B	0.8727	0.3446	0.2458	0.091*
H13C	1.0438	0.4794	0.2905	0.091*
C14	0.5505 (2)	0.41942 (15)	0.14984 (10)	0.0436 (3)
C15	0.3012 (10)	0.3078 (6)	0.0336 (4)	0.0601 (14)	0.609 (6)
H15A	0.2845	0.2090	0.0467	0.072*	0.609 (6)
H15B	0.3884	0.3257	−0.0170	0.072*	0.609 (6)
C16	0.1147 (5)	0.3283 (6)	0.0039 (3)	0.101 (2)	0.609 (6)
H16A	0.0707	0.2739	−0.0598	0.151*	0.609 (6)
H16B	0.1299	0.4304	0.0031	0.151*	0.609 (6)
H16C	0.0237	0.2938	0.0493	0.151*	0.609 (6)
C15'	0.2769 (16)	0.3466 (8)	0.0264 (6)	0.060 (2)	0.391 (6)
H15C	0.3674	0.3276	−0.0192	0.072*	0.391 (6)
H15D	0.2102	0.4088	0.0010	0.072*	0.391 (6)
C16'	0.1393 (9)	0.2054 (7)	0.0435 (4)	0.087 (2)	0.391 (6)
H16D	0.0707	0.1536	−0.0169	0.131*	0.391 (6)
H16E	0.0515	0.2265	0.0889	0.131*	0.391 (6)
H16F	0.2079	0.1460	0.0692	0.131*	0.391 (6)
C17	0.52448 (18)	0.74910 (14)	0.23461 (9)	0.0382 (3)
C18	0.3791 (2)	0.75906 (18)	0.17376 (12)	0.0542 (4)
H18	0.2641	0.6854	0.1657	0.065*
C19	0.4008 (3)	0.8766 (2)	0.12439 (13)	0.0653 (5)
H19	0.3011	0.8801	0.0830	0.078*
C20	0.5650 (3)	0.98628 (19)	0.13566 (12)	0.0629 (5)
H20	0.5786	1.0659	0.1031	0.075*
C21	0.7100 (3)	0.9784 (2)	0.19528 (16)	0.0760 (6)
H21	0.8239	1.0531	0.2032	0.091*
C22	0.6909 (2)	0.86116 (19)	0.24438 (14)	0.0644 (5)
H22	0.7923	0.8580	0.2847	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0253 (4)	0.0631 (7)	0.0601 (6)	0.0167 (4)	−0.0015 (4)	−0.0010 (5)
O2	0.0783 (9)	0.0794 (9)	0.0642 (8)	0.0368 (7)	−0.0039 (6)	−0.0231 (6)
O3	0.0480 (6)	0.0667 (7)	0.0437 (6)	0.0101 (5)	−0.0078 (5)	−0.0091 (5)
N1	0.0226 (5)	0.0514 (7)	0.0460 (6)	0.0130 (4)	−0.0010 (4)	0.0002 (5)
C1	0.0254 (5)	0.0343 (6)	0.0382 (6)	0.0086 (4)	0.0010 (5)	0.0057 (5)
C2	0.0292 (6)	0.0431 (7)	0.0403 (7)	0.0108 (5)	−0.0047 (5)	0.0064 (5)
C3	0.0364 (6)	0.0404 (7)	0.0377 (7)	0.0093 (5)	−0.0008 (5)	0.0026 (5)
C4	0.0344 (6)	0.0476 (7)	0.0406 (7)	0.0126 (5)	0.0070 (5)	0.0061 (6)
C5	0.0269 (6)	0.0313 (6)	0.0438 (7)	0.0090 (4)	0.0020 (5)	0.0070 (5)
C6	0.0262 (5)	0.0333 (6)	0.0358 (6)	0.0090 (4)	0.0006 (4)	0.0056 (5)
C7	0.0579 (9)	0.0381 (8)	0.0743 (11)	0.0086 (7)	−0.0004 (8)	0.0051 (7)
C8	0.0567 (10)	0.0840 (12)	0.0411 (8)	0.0180 (9)	−0.0032 (7)	−0.0033 (8)
C10	0.0247 (5)	0.0388 (6)	0.0367 (6)	0.0077 (5)	−0.0022 (4)	0.0032 (5)
C11	0.0331 (6)	0.0356 (6)	0.0377 (6)	0.0078 (5)	0.0038 (5)	0.0049 (5)
C12	0.0313 (6)	0.0409 (7)	0.0435 (7)	0.0101 (5)	0.0071 (5)	0.0046 (5)
C13	0.0422 (8)	0.0713 (11)	0.0683 (10)	0.0269 (7)	0.0059 (7)	−0.0086 (8)
C14	0.0467 (8)	0.0410 (7)	0.0402 (7)	0.0090 (6)	0.0030 (6)	0.0043 (6)
C15	0.058 (2)	0.068 (3)	0.045 (2)	0.017 (2)	−0.0148 (15)	−0.013 (2)
C16	0.058 (2)	0.160 (5)	0.068 (2)	0.033 (2)	−0.0198 (17)	−0.035 (3)
C15'	0.073 (5)	0.061 (4)	0.042 (3)	0.018 (3)	−0.011 (3)	0.002 (3)
C16'	0.083 (4)	0.086 (4)	0.066 (3)	−0.006 (3)	−0.001 (3)	−0.011 (3)
C17	0.0397 (7)	0.0417 (7)	0.0341 (6)	0.0151 (5)	−0.0006 (5)	0.0035 (5)
C18	0.0492 (8)	0.0576 (9)	0.0572 (9)	0.0180 (7)	−0.0099 (7)	0.0118 (7)
C19	0.0742 (11)	0.0711 (11)	0.0596 (10)	0.0339 (10)	−0.0114 (9)	0.0177 (8)
C20	0.0906 (13)	0.0535 (9)	0.0528 (9)	0.0300 (9)	0.0043 (9)	0.0174 (7)
C21	0.0701 (12)	0.0607 (11)	0.0899 (14)	−0.0019 (9)	−0.0095 (10)	0.0331 (10)
C22	0.0498 (9)	0.0603 (10)	0.0781 (12)	0.0010 (7)	−0.0178 (8)	0.0298 (9)

Geometric parameters (Å, º) top

O1—C5	1.2307 (14)	C11—C12	1.3498 (18)
O2—C14	1.2023 (18)	C11—C14	1.4706 (18)
O3—C14	1.3364 (18)	C12—C13	1.4992 (19)
O3—C15'	1.466 (6)	C13—H13A	0.9600
O3—C15	1.470 (4)	C13—H13B	0.9600
N1—C1	1.3652 (16)	C13—H13C	0.9600
N1—C12	1.3848 (17)	C15—C16	1.493 (6)
N1—H1	0.868 (9)	C15—H15A	0.9700
C1—C6	1.3557 (16)	C15—H15B	0.9700
C1—C2	1.4930 (17)	C16—H16A	0.9600
C2—C3	1.5249 (18)	C16—H16B	0.9600
C2—H2A	0.9700	C16—H16C	0.9600
C2—H2B	0.9700	C15'—C16'	1.506 (9)
C3—C7	1.526 (2)	C15'—H15C	0.9700
C3—C4	1.5290 (18)	C15'—H15D	0.9700
C3—C8	1.531 (2)	C16'—H16D	0.9600
C4—C5	1.5032 (18)	C16'—H16E	0.9600
C4—H4A	0.9700	C16'—H16F	0.9600
C4—H4B	0.9700	C17—C22	1.374 (2)
C5—C6	1.4437 (17)	C17—C18	1.3775 (19)
C6—C10	1.5121 (17)	C18—C19	1.384 (2)
C7—H7A	0.9600	C18—H18	0.9300
C7—H7B	0.9600	C19—C20	1.350 (3)
C7—H7C	0.9600	C19—H19	0.9300
C8—H8A	0.9600	C20—C21	1.357 (3)
C8—H8B	0.9600	C20—H20	0.9300
C8—H8C	0.9600	C21—C22	1.381 (2)
C10—C17	1.5230 (18)	C21—H21	0.9300
C10—C11	1.5242 (17)	C22—H22	0.9300
C10—H10	0.9800

C14—O3—C15'	124.4 (5)	C12—C11—C10	120.57 (11)
C14—O3—C15	110.9 (3)	C14—C11—C10	119.40 (11)
C1—N1—C12	122.25 (10)	C11—C12—N1	119.49 (11)
C1—N1—H1	119.8 (11)	C11—C12—C13	127.20 (13)
C12—N1—H1	116.6 (11)	N1—C12—C13	113.23 (12)
C6—C1—N1	119.61 (11)	C12—C13—H13A	109.5
C6—C1—C2	124.11 (11)	C12—C13—H13B	109.5
N1—C1—C2	116.17 (10)	H13A—C13—H13B	109.5
C1—C2—C3	113.38 (10)	C12—C13—H13C	109.5
C1—C2—H2A	108.9	H13A—C13—H13C	109.5
C3—C2—H2A	108.9	H13B—C13—H13C	109.5
C1—C2—H2B	108.9	O2—C14—O3	121.58 (13)
C3—C2—H2B	108.9	O2—C14—C11	126.43 (14)
H2A—C2—H2B	107.7	O3—C14—C11	112.00 (12)
C2—C3—C7	111.03 (12)	O3—C15—C16	105.3 (4)
C2—C3—C4	107.82 (10)	O3—C15—H15A	110.7
C7—C3—C4	110.04 (12)	C16—C15—H15A	110.7
C2—C3—C8	108.95 (12)	O3—C15—H15B	110.7
C7—C3—C8	109.41 (13)	C16—C15—H15B	110.7
C4—C3—C8	109.56 (12)	H15A—C15—H15B	108.8
C5—C4—C3	115.31 (11)	O3—C15'—C16'	104.8 (6)
C5—C4—H4A	108.4	O3—C15'—H15C	110.8
C3—C4—H4A	108.4	C16'—C15'—H15C	110.8
C5—C4—H4B	108.4	O3—C15'—H15D	110.8
C3—C4—H4B	108.4	C16'—C15'—H15D	110.8
H4A—C4—H4B	107.5	H15C—C15'—H15D	108.9
O1—C5—C6	121.51 (12)	C15'—C16'—H16D	109.5
O1—C5—C4	119.89 (11)	C15'—C16'—H16E	109.5
C6—C5—C4	118.53 (10)	H16D—C16'—H16E	109.5
C1—C6—C5	119.17 (11)	C15'—C16'—H16F	109.5
C1—C6—C10	120.72 (10)	H16D—C16'—H16F	109.5
C5—C6—C10	120.10 (10)	H16E—C16'—H16F	109.5
C3—C7—H7A	109.5	C22—C17—C18	117.07 (14)
C3—C7—H7B	109.5	C22—C17—C10	121.47 (12)
H7A—C7—H7B	109.5	C18—C17—C10	121.42 (12)
C3—C7—H7C	109.5	C17—C18—C19	121.25 (16)
H7A—C7—H7C	109.5	C17—C18—H18	119.4
H7B—C7—H7C	109.5	C19—C18—H18	119.4
C3—C8—H8A	109.5	C20—C19—C18	120.74 (16)
C3—C8—H8B	109.5	C20—C19—H19	119.6
H8A—C8—H8B	109.5	C18—C19—H19	119.6
C3—C8—H8C	109.5	C19—C20—C21	118.86 (16)
H8A—C8—H8C	109.5	C19—C20—H20	120.6
H8B—C8—H8C	109.5	C21—C20—H20	120.6
C6—C10—C17	112.36 (10)	C20—C21—C22	121.03 (17)
C6—C10—C11	109.62 (10)	C20—C21—H21	119.5
C17—C10—C11	111.30 (10)	C22—C21—H21	119.5
C6—C10—H10	107.8	C17—C22—C21	121.04 (15)
C17—C10—H10	107.8	C17—C22—H22	119.5
C11—C10—H10	107.8	C21—C22—H22	119.5
C12—C11—C14	120.00 (12)

C12—N1—C1—C6	−14.66 (19)	C10—C11—C12—N1	5.87 (19)
C12—N1—C1—C2	161.64 (12)	C14—C11—C12—C13	0.7 (2)
C6—C1—C2—C3	−21.55 (17)	C10—C11—C12—C13	−177.44 (14)
N1—C1—C2—C3	162.33 (11)	C1—N1—C12—C11	16.3 (2)
C1—C2—C3—C7	−72.94 (14)	C1—N1—C12—C13	−160.84 (13)
C1—C2—C3—C4	47.67 (14)	C15'—O3—C14—O2	−11.4 (5)
C1—C2—C3—C8	166.50 (12)	C15—O3—C14—O2	3.4 (4)
C2—C3—C4—C5	−50.59 (15)	C15'—O3—C14—C11	168.4 (4)
C7—C3—C4—C5	70.64 (15)	C15—O3—C14—C11	−176.8 (3)
C8—C3—C4—C5	−169.02 (12)	C12—C11—C14—O2	−5.1 (2)
C3—C4—C5—O1	−157.03 (12)	C10—C11—C14—O2	172.99 (15)
C3—C4—C5—C6	25.84 (17)	C12—C11—C14—O3	175.07 (12)
N1—C1—C6—C5	169.51 (11)	C10—C11—C14—O3	−6.81 (17)
C2—C1—C6—C5	−6.49 (18)	C14—O3—C15—C16	−172.8 (4)
N1—C1—C6—C10	−9.10 (18)	C15'—O3—C15—C16	−34 (2)
C2—C1—C6—C10	174.90 (11)	C14—O3—C15'—C16'	104.6 (8)
O1—C5—C6—C1	−172.73 (12)	C15—O3—C15'—C16'	56.8 (19)
C4—C5—C6—C1	4.35 (17)	C6—C10—C17—C22	53.16 (18)
O1—C5—C6—C10	5.89 (18)	C11—C10—C17—C22	−70.21 (17)
C4—C5—C6—C10	−177.03 (11)	C6—C10—C17—C18	−129.18 (14)
C1—C6—C10—C17	−96.98 (13)	C11—C10—C17—C18	107.45 (15)
C5—C6—C10—C17	84.42 (13)	C22—C17—C18—C19	0.3 (2)
C1—C6—C10—C11	27.33 (15)	C10—C17—C18—C19	−177.41 (14)
C5—C6—C10—C11	−151.27 (11)	C17—C18—C19—C20	−0.9 (3)
C6—C10—C11—C12	−25.63 (16)	C18—C19—C20—C21	0.9 (3)
C17—C10—C11—C12	99.29 (14)	C19—C20—C21—C22	−0.4 (3)
C6—C10—C11—C14	156.26 (11)	C18—C17—C22—C21	0.2 (3)
C17—C10—C11—C14	−78.82 (14)	C10—C17—C22—C21	177.95 (17)
C14—C11—C12—N1	−176.02 (12)	C20—C21—C22—C17	−0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.87 (1)	2.04 (1)	2.890 (1)	168 (2)

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₅NO₃
M_r	339.42
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.3523 (4), 9.6349 (5), 13.9495 (7)
α, β, γ (°)	98.370 (1), 91.778 (1), 106.291 (1)
V (Å³)	935.70 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10191, 4302, 3439
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.135, 1.03
No. of reflections	4302
No. of parameters	254
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.20

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.87 (1)	2.04 (1)	2.890 (1)	168 (2)

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

Acknowledgements

The authors thank Baku State University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Duque, J., Pomes, R., Suarez, M., Ochoa, E., Punte, G. & Echevarria, G. E. (2000). Bol. Soc. Chil. Quim. 45, 175–180. CAS Google Scholar
Safari, J., Banitaba, S. H. & Dehghan Khalili, S. (2011). Cuihua Xuebao, 32, 1850–1855. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 2,7,7-tri­methyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

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organic compounds

Ethyl 2,7,7-trimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate