Ethyl 2-methyl-5-oxo-4-(3,4,5-trimeth­oxy­phen­yl)-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate

Natarajan, S.; Indumathi, P.; Reddy, B.P.; Vijayakumar, V.; Lakshman, P.L.N.

doi:10.1107/S1600536810030333

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2240

https://doi.org/10.1107/S1600536810030333

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Ethyl 2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

S. Natarajan,^a P. Indumathi,^a B. Palakshi Reddy,^b V. Vijayakumar ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, Madurai Kamaraj University, Madurai 625 021, India, ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 104, India, and ^cDepartment of Food Science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya (81100), Sri Lanka
^*Correspondence e-mail: nilanthalakshman@yahoo.co.uk

(Received 12 July 2010; accepted 29 July 2010; online 11 August 2010)

In the molecular structure of the title compound, C₂₂H₂₇NO₆, the dihydropyridine ring adopts a flattened boat conformation while the cyclohexenone ring is in an envelope conformation. In the crystal, molecules stack parallel to the crystallographic a axis linked by intermolecular N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For general background to the biological activity of quinoline derivatives, see: Baba (1997 ); Baba et al. (1997 ,1998 ); Davies et al. (2005 ); Rose & Draeger et al. (1992 ); Warrior et al. (2005 ).

Experimental

Crystal data

C₂₂H₂₇NO₆
M_r = 401.44
Triclinic, $[P \overline 1]$
a = 7.512 (2) Å
b = 10.402 (1) Å
c = 14.568 (3) Å
α = 109.77 (3)°
β = 95.42 (1)°
γ = 104.41 (2)°
V = 1017.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 K
0.26 × 0.24 × 0.21 mm

Data collection

Nonius MACH3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.976, T_max = 0.980
4471 measured reflections
3574 independent reflections
2653 reflections with I > 2σ(I)
R_int = 0.013
3 standard reflections every 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.129
S = 1.03
3574 reflections
268 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.83 (3)	2.21 (3)	2.995 (2)	160 (3)
C2—H2B⋯O4ⁱⁱ	0.97	2.55	3.340 (3)	138
C10—H10B⋯O1ⁱ	0.96	2.59	3.429 (3)	146
Symmetry codes: (i) x-1, y, z; (ii) x-1, y-1, z.

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: https://doi.org/10.1107/S1600536810030333/jh2183sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030333/jh2183Isup2.hkl

checkCIF report

Comment top

Some derivatives of quinoline are naturally occurring alkaloids and are very attractive for their various bioactivities. For example, they have calcium modulatory properties (Rose &Draeger, 1992), antibacterial activity (Davies et al., 2005),fungicidal activity (Warrior et al., 2005) and selective inhibitor of human immunodeficiency virus type I (HIV-1) transcription (Baba, 1997; Baba et al.,1997,1998) etc. Due to these significant biological activities, the structure of a quinoline derivative, ethyl 2-methyl-5-oxo -4-(3,4,5-trimethoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate is elucidated and reported.

The dihydropyridine ring of the title molecule adopts a flattened boat conformation. The cyclohexenone ring is in an envelope conformation with atom C3 at the flap. The 3,4,5-trimethoxyphenyl ring and the plane of the dihydropyridine ring (N1/C1/C6/C7/C8/C9) are nearly perpendicular to each other, with a dihedral angle of 89.33 (4)°. In the crystal structure, molecules are linked into a sheet (Fig.2) parallel to the a axis by N—H···O and C—H···O intra and intermolecular hydrogen bonds (Table 1). Further, it is observed that these sheets are assembled through centrosymmetrically related pairs of molecules by C2—H2B···O4 inter molecular hydrogen bond and weak interactions, which stabilize the structure.

Related literature top

For general background to the biological activity of quinoline derivatives, see: Baba (1997); Baba et al. (1997,1998); Davies et al. (2005); Rose & Draeger et al. (1992); Warrior et al. (2005).

Experimental top

3,4,5-trimethoxy benzaldehyde (10 mmol), 1,3-cyclohexanedione (10 mmol) and ethyl acetoacetate (10 mmol) were mixed along with 20 ml of ethanol. Ammonium acetate (10 mmol) was added to the mixture and refluxed on water bath for about 1 h. The progress of the reaction was monitored by TLC. After confirming that the reaction got completed, the reaction mixture was allowed to cool to room temperature and left aside for a day. Solid crystals started to grow from the mother liquor. It was filtered and washed with diethyl ether to ensure pure crystals [yield: 60%, m.p. 576–578 K].

Structure description top

For general background to the biological activity of quinoline derivatives, see: Baba (1997); Baba et al. (1997,1998); Davies et al. (2005); Rose & Draeger et al. (1992); Warrior et al. (2005).

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 (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing diagram showing the sheets of hydrogen bonds along the a axis

Ethyl 2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-1,4,5,6,7,8- hexahydroquinoline-3-carboxylate top

Crystal data top

C₂₂H₂₇NO₆	Z = 2
M_r = 401.44	F(000) = 428
Triclinic, P1	D_x = 1.310 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.512 (2) Å	Cell parameters from 25 reflections
b = 10.402 (1) Å	θ = 2–25°
c = 14.568 (3) Å	µ = 0.10 mm⁻¹
α = 109.77 (3)°	T = 294 K
β = 95.42 (1)°	Block, colourless
γ = 104.41 (2)°	0.26 × 0.24 × 0.21 mm
V = 1017.4 (4) Å³

Data collection top

Nonius MACH3 diffractometer	2653 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.013
Graphite monochromator	θ_max = 25.0°, θ_min = 2.1°
ω–2θ scans	h = −1→8
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
T_min = 0.976, T_max = 0.980	l = −17→17
4471 measured reflections	3 standard reflections every 60 min
3574 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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0609P)² + 0.3979P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3574 reflections	Δρ_max = 0.23 e Å⁻³
268 parameters	Δρ_min = −0.18 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: 0.013 (3)

Crystal data top

C₂₂H₂₇NO₆	γ = 104.41 (2)°
M_r = 401.44	V = 1017.4 (4) Å³
Triclinic, P1	Z = 2
a = 7.512 (2) Å	Mo Kα radiation
b = 10.402 (1) Å	µ = 0.10 mm⁻¹
c = 14.568 (3) Å	T = 294 K
α = 109.77 (3)°	0.26 × 0.24 × 0.21 mm
β = 95.42 (1)°

Data collection top

Nonius MACH3 diffractometer	2653 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.013
T_min = 0.976, T_max = 0.980	3 standard reflections every 60 min
4471 measured reflections	intensity decay: none
3574 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.23 e Å⁻³
3574 reflections	Δρ_min = −0.18 e Å⁻³
268 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
C22	0.4600 (4)	0.2952 (4)	0.0056 (2)	0.0841 (9)
H22A	0.4922	0.3586	−0.0293	0.101*
H22B	0.3534	0.2153	−0.0339	0.101*
H22C	0.5642	0.2613	0.0178	0.101*
H1N	−0.286 (4)	−0.135 (3)	0.2897 (18)	0.061 (7)*
O4	0.68460 (19)	0.35699 (15)	0.22606 (11)	0.0519 (4)
O3	0.36747 (19)	0.26111 (15)	0.50993 (10)	0.0523 (4)
N1	−0.1712 (2)	−0.09684 (18)	0.30488 (13)	0.0405 (4)
O1	0.41288 (19)	−0.16053 (16)	0.25103 (12)	0.0588 (4)
C6	0.1238 (2)	−0.11864 (19)	0.27165 (13)	0.0323 (4)
C1	−0.0644 (2)	−0.17812 (19)	0.25700 (13)	0.0347 (4)
C8	0.0925 (2)	0.09809 (19)	0.40306 (13)	0.0346 (4)
C9	−0.0944 (2)	0.0320 (2)	0.38398 (14)	0.0356 (4)
C15	0.4536 (2)	0.20151 (19)	0.27900 (14)	0.0371 (4)
H15	0.5452	0.1991	0.3256	0.044*
O2	0.0990 (2)	0.30115 (19)	0.54511 (14)	0.0765 (6)
C5	0.2404 (3)	−0.2085 (2)	0.23209 (15)	0.0407 (5)
C16	0.5036 (3)	0.28065 (19)	0.22121 (15)	0.0388 (4)
O6	0.4166 (2)	0.36880 (18)	0.09651 (13)	0.0659 (5)
C19	0.1316 (3)	0.1295 (2)	0.19881 (14)	0.0393 (4)
H19	0.0068	0.0788	0.1914	0.047*
C7	0.2165 (2)	0.03861 (18)	0.33288 (13)	0.0330 (4)
H7	0.3332	0.0471	0.3740	0.040*
C14	0.2679 (2)	0.12545 (18)	0.26814 (13)	0.0332 (4)
O5	0.0588 (2)	0.21801 (19)	0.06860 (13)	0.0656 (5)
C3	−0.0564 (3)	−0.3963 (2)	0.12134 (17)	0.0557 (6)
H3A	−0.0602	−0.3578	0.0694	0.067*
H3B	−0.1143	−0.4991	0.0910	0.067*
C18	0.1810 (3)	0.2088 (2)	0.14062 (15)	0.0430 (5)
C17	0.3684 (3)	0.2858 (2)	0.15175 (15)	0.0438 (5)
C11	0.1788 (3)	0.2281 (2)	0.49145 (15)	0.0446 (5)
C2	−0.1646 (3)	−0.3315 (2)	0.19699 (16)	0.0448 (5)
H2A	−0.2869	−0.3398	0.1631	0.054*
H2B	−0.1832	−0.3840	0.2408	0.054*
C10	−0.2342 (3)	0.0813 (2)	0.44419 (16)	0.0479 (5)
H10A	−0.1986	0.0885	0.5112	0.058*
H10B	−0.3565	0.0135	0.4152	0.058*
H10C	−0.2366	0.1733	0.4445	0.058*
C4	0.1457 (3)	−0.3643 (2)	0.16960 (18)	0.0539 (6)
H4A	0.1496	−0.4198	0.2111	0.065*
H4B	0.2156	−0.3952	0.1179	0.065*
C20	−0.1304 (3)	0.1336 (3)	0.04654 (18)	0.0630 (7)
H20A	−0.1993	0.1503	−0.0050	0.076*
H20B	−0.1835	0.1588	0.1051	0.076*
H20C	−0.1369	0.0342	0.0244	0.076*
C21	0.8277 (3)	0.3578 (3)	0.29756 (19)	0.0573 (6)
H21A	0.9466	0.4146	0.2935	0.069*
H21B	0.8305	0.2616	0.2845	0.069*
H21C	0.8025	0.3978	0.3630	0.069*
C13	0.6642 (3)	0.4322 (3)	0.5930 (2)	0.0768 (8)
H13A	0.7287	0.5156	0.6512	0.092*
H13B	0.6768	0.4544	0.5347	0.092*
H13C	0.7174	0.3564	0.5904	0.092*
C12	0.4662 (3)	0.3867 (3)	0.59723 (18)	0.0667 (7)
H12A	0.4530	0.3652	0.6565	0.080*
H12B	0.4124	0.4635	0.6007	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C22	0.0715 (18)	0.133 (3)	0.080 (2)	0.0367 (18)	0.0272 (15)	0.072 (2)
O4	0.0339 (8)	0.0517 (9)	0.0690 (10)	0.0004 (6)	0.0116 (7)	0.0298 (8)
O3	0.0343 (8)	0.0524 (9)	0.0480 (8)	0.0054 (6)	0.0031 (6)	−0.0016 (7)
N1	0.0211 (8)	0.0445 (9)	0.0519 (10)	0.0076 (7)	0.0058 (7)	0.0150 (8)
O1	0.0272 (8)	0.0560 (9)	0.0804 (11)	0.0141 (7)	0.0118 (7)	0.0085 (8)
C6	0.0257 (9)	0.0357 (10)	0.0354 (9)	0.0083 (7)	0.0064 (7)	0.0137 (8)
C1	0.0276 (9)	0.0381 (10)	0.0394 (10)	0.0079 (8)	0.0057 (8)	0.0172 (8)
C8	0.0294 (9)	0.0378 (10)	0.0375 (10)	0.0117 (8)	0.0073 (8)	0.0139 (8)
C9	0.0310 (10)	0.0411 (10)	0.0407 (10)	0.0154 (8)	0.0094 (8)	0.0189 (8)
C15	0.0280 (9)	0.0374 (10)	0.0428 (11)	0.0072 (8)	0.0046 (8)	0.0139 (8)
O2	0.0504 (10)	0.0693 (11)	0.0758 (12)	0.0162 (8)	0.0164 (9)	−0.0140 (9)
C5	0.0321 (10)	0.0433 (11)	0.0455 (11)	0.0111 (8)	0.0085 (8)	0.0152 (9)
C16	0.0322 (10)	0.0323 (10)	0.0487 (11)	0.0065 (8)	0.0120 (8)	0.0128 (8)
O6	0.0674 (11)	0.0684 (11)	0.0800 (12)	0.0172 (9)	0.0201 (9)	0.0508 (10)
C19	0.0279 (9)	0.0405 (10)	0.0452 (11)	0.0065 (8)	0.0061 (8)	0.0138 (9)
C7	0.0230 (8)	0.0367 (10)	0.0379 (10)	0.0082 (7)	0.0054 (7)	0.0129 (8)
C14	0.0278 (9)	0.0311 (9)	0.0370 (10)	0.0084 (7)	0.0077 (7)	0.0082 (8)
O5	0.0493 (10)	0.0834 (12)	0.0730 (11)	0.0173 (8)	−0.0018 (8)	0.0458 (10)
C3	0.0474 (13)	0.0447 (12)	0.0554 (13)	0.0020 (10)	0.0087 (10)	0.0035 (10)
C18	0.0408 (11)	0.0454 (11)	0.0438 (11)	0.0160 (9)	0.0042 (9)	0.0167 (9)
C17	0.0456 (12)	0.0406 (11)	0.0496 (12)	0.0129 (9)	0.0128 (9)	0.0215 (9)
C11	0.0380 (11)	0.0462 (11)	0.0463 (11)	0.0114 (9)	0.0111 (9)	0.0133 (9)
C2	0.0322 (10)	0.0419 (11)	0.0521 (12)	0.0030 (8)	0.0034 (9)	0.0145 (9)
C10	0.0340 (11)	0.0593 (13)	0.0570 (13)	0.0217 (9)	0.0163 (9)	0.0223 (10)
C4	0.0470 (12)	0.0435 (12)	0.0636 (14)	0.0163 (10)	0.0146 (11)	0.0080 (10)
C20	0.0466 (13)	0.0887 (18)	0.0515 (13)	0.0309 (13)	0.0002 (10)	0.0186 (13)
C21	0.0307 (11)	0.0586 (14)	0.0789 (16)	0.0055 (10)	0.0112 (11)	0.0268 (12)
C13	0.0482 (14)	0.0747 (17)	0.0697 (17)	0.0042 (12)	−0.0008 (12)	−0.0059 (14)
C12	0.0475 (13)	0.0650 (15)	0.0528 (14)	0.0008 (11)	0.0051 (11)	−0.0078 (12)

Geometric parameters (Å, º) top

C22—O6	1.402 (3)	C19—H19	0.9300
C22—H22A	0.9600	C7—C14	1.525 (2)
C22—H22B	0.9600	C7—H7	0.9800
C22—H22C	0.9600	O5—C18	1.372 (2)
O4—C16	1.375 (2)	O5—C20	1.413 (3)
O4—C21	1.421 (3)	C3—C2	1.506 (3)
O3—C11	1.350 (2)	C3—C4	1.516 (3)
O3—C12	1.446 (3)	C3—H3A	0.9700
N1—C1	1.374 (2)	C3—H3B	0.9700
N1—C9	1.379 (3)	C18—C17	1.399 (3)
N1—H1N	0.83 (3)	C2—H2A	0.9700
O1—C5	1.234 (2)	C2—H2B	0.9700
C6—C1	1.358 (2)	C10—H10A	0.9600
C6—C5	1.453 (3)	C10—H10B	0.9600
C6—C7	1.512 (3)	C10—H10C	0.9600
C1—C2	1.486 (3)	C4—H4A	0.9700
C8—C9	1.355 (2)	C4—H4B	0.9700
C8—C11	1.461 (3)	C20—H20A	0.9600
C8—C7	1.528 (2)	C20—H20B	0.9600
C9—C10	1.508 (3)	C20—H20C	0.9600
C15—C16	1.379 (3)	C21—H21A	0.9600
C15—C14	1.386 (2)	C21—H21B	0.9600
C15—H15	0.9300	C21—H21C	0.9600
O2—C11	1.209 (2)	C13—C12	1.458 (3)
C5—C4	1.505 (3)	C13—H13A	0.9600
C16—C17	1.389 (3)	C13—H13B	0.9600
O6—C17	1.376 (2)	C13—H13C	0.9600
C19—C18	1.384 (3)	C12—H12A	0.9700
C19—C14	1.387 (3)	C12—H12B	0.9700

O6—C22—H22A	109.5	O5—C18—C19	125.06 (18)
O6—C22—H22B	109.5	O5—C18—C17	114.73 (18)
H22A—C22—H22B	109.5	C19—C18—C17	120.20 (18)
O6—C22—H22C	109.5	O6—C17—C16	120.62 (18)
H22A—C22—H22C	109.5	O6—C17—C18	120.21 (18)
H22B—C22—H22C	109.5	C16—C17—C18	119.13 (18)
C16—O4—C21	117.61 (16)	O2—C11—O3	121.13 (19)
C11—O3—C12	116.21 (17)	O2—C11—C8	126.93 (19)
C1—N1—C9	122.70 (16)	O3—C11—C8	111.93 (16)
C1—N1—H1N	116.1 (17)	C1—C2—C3	111.44 (16)
C9—N1—H1N	120.6 (17)	C1—C2—H2A	109.3
C1—C6—C5	119.71 (16)	C3—C2—H2A	109.3
C1—C6—C7	121.31 (16)	C1—C2—H2B	109.3
C5—C6—C7	118.90 (15)	C3—C2—H2B	109.3
C6—C1—N1	119.52 (17)	H2A—C2—H2B	108.0
C6—C1—C2	124.04 (17)	C9—C10—H10A	109.5
N1—C1—C2	116.30 (16)	C9—C10—H10B	109.5
C9—C8—C11	120.34 (17)	H10A—C10—H10B	109.5
C9—C8—C7	120.86 (17)	C9—C10—H10C	109.5
C11—C8—C7	118.80 (16)	H10A—C10—H10C	109.5
C8—C9—N1	119.58 (17)	H10B—C10—H10C	109.5
C8—C9—C10	126.59 (18)	C5—C4—C3	113.84 (18)
N1—C9—C10	113.77 (16)	C5—C4—H4A	108.8
C16—C15—C14	120.44 (18)	C3—C4—H4A	108.8
C16—C15—H15	119.8	C5—C4—H4B	108.8
C14—C15—H15	119.8	C3—C4—H4B	108.8
O1—C5—C6	121.43 (18)	H4A—C4—H4B	107.7
O1—C5—C4	120.26 (18)	O5—C20—H20A	109.5
C6—C5—C4	118.29 (16)	O5—C20—H20B	109.5
O4—C16—C15	124.14 (18)	H20A—C20—H20B	109.5
O4—C16—C17	115.44 (17)	O5—C20—H20C	109.5
C15—C16—C17	120.42 (17)	H20A—C20—H20C	109.5
C17—O6—C22	113.52 (19)	H20B—C20—H20C	109.5
C18—C19—C14	120.14 (17)	O4—C21—H21A	109.5
C18—C19—H19	119.9	O4—C21—H21B	109.5
C14—C19—H19	119.9	H21A—C21—H21B	109.5
C6—C7—C14	112.18 (15)	O4—C21—H21C	109.5
C6—C7—C8	110.40 (14)	H21A—C21—H21C	109.5
C14—C7—C8	111.39 (14)	H21B—C21—H21C	109.5
C6—C7—H7	107.6	C12—C13—H13A	109.5
C14—C7—H7	107.6	C12—C13—H13B	109.5
C8—C7—H7	107.6	H13A—C13—H13B	109.5
C15—C14—C19	119.66 (17)	C12—C13—H13C	109.5
C15—C14—C7	119.36 (16)	H13A—C13—H13C	109.5
C19—C14—C7	120.98 (16)	H13B—C13—H13C	109.5
C18—O5—C20	118.35 (18)	O3—C12—C13	110.0 (2)
C2—C3—C4	110.79 (18)	O3—C12—H12A	109.7
C2—C3—H3A	109.5	C13—C12—H12A	109.7
C4—C3—H3A	109.5	O3—C12—H12B	109.7
C2—C3—H3B	109.5	C13—C12—H12B	109.7
C4—C3—H3B	109.5	H12A—C12—H12B	108.2
H3A—C3—H3B	108.1

C5—C6—C1—N1	171.81 (16)	C6—C7—C14—C15	−120.58 (18)
C7—C6—C1—N1	−5.1 (3)	C8—C7—C14—C15	115.10 (18)
C5—C6—C1—C2	−3.6 (3)	C6—C7—C14—C19	59.5 (2)
C7—C6—C1—C2	179.45 (17)	C8—C7—C14—C19	−64.8 (2)
C9—N1—C1—C6	−14.9 (3)	C20—O5—C18—C19	−4.4 (3)
C9—N1—C1—C2	160.86 (18)	C20—O5—C18—C17	174.56 (19)
C11—C8—C9—N1	−174.65 (17)	C14—C19—C18—O5	178.62 (19)
C7—C8—C9—N1	5.4 (3)	C14—C19—C18—C17	−0.3 (3)
C11—C8—C9—C10	2.4 (3)	C22—O6—C17—C16	91.5 (3)
C7—C8—C9—C10	−177.55 (17)	C22—O6—C17—C18	−90.4 (3)
C1—N1—C9—C8	14.7 (3)	O4—C16—C17—O6	−3.2 (3)
C1—N1—C9—C10	−162.71 (17)	C15—C16—C17—O6	177.59 (18)
C1—C6—C5—O1	−173.80 (19)	O4—C16—C17—C18	178.77 (17)
C7—C6—C5—O1	3.2 (3)	C15—C16—C17—C18	−0.5 (3)
C1—C6—C5—C4	4.2 (3)	O5—C18—C17—O6	3.4 (3)
C7—C6—C5—C4	−178.84 (18)	C19—C18—C17—O6	−177.62 (18)
C21—O4—C16—C15	−2.2 (3)	O5—C18—C17—C16	−178.56 (18)
C21—O4—C16—C17	178.60 (18)	C19—C18—C17—C16	0.5 (3)
C14—C15—C16—O4	−178.84 (17)	C12—O3—C11—O2	0.6 (3)
C14—C15—C16—C17	0.3 (3)	C12—O3—C11—C8	−178.82 (19)
C1—C6—C7—C14	−103.04 (19)	C9—C8—C11—O2	−12.8 (3)
C5—C6—C7—C14	80.0 (2)	C7—C8—C11—O2	167.2 (2)
C1—C6—C7—C8	21.8 (2)	C9—C8—C11—O3	166.62 (17)
C5—C6—C7—C8	−155.10 (16)	C7—C8—C11—O3	−13.4 (2)
C9—C8—C7—C6	−22.0 (2)	C6—C1—C2—C3	−24.4 (3)
C11—C8—C7—C6	158.08 (16)	N1—C1—C2—C3	160.04 (18)
C9—C8—C7—C14	103.36 (19)	C4—C3—C2—C1	49.9 (3)
C11—C8—C7—C14	−76.6 (2)	O1—C5—C4—C3	−158.6 (2)
C16—C15—C14—C19	−0.2 (3)	C6—C5—C4—C3	23.5 (3)
C16—C15—C14—C7	179.89 (16)	C2—C3—C4—C5	−50.4 (3)
C18—C19—C14—C15	0.1 (3)	C11—O3—C12—C13	−164.3 (2)
C18—C19—C14—C7	−179.92 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3	0.98	2.36	2.720 (2)	101
N1—H1N···O1ⁱ	0.83 (3)	2.21 (3)	2.995 (2)	160 (3)
C2—H2B···O4ⁱⁱ	0.97	2.55	3.340 (3)	138
C10—H10B···O1ⁱ	0.96	2.59	3.429 (3)	146

Symmetry codes: (i) x−1, y, z; (ii) x−1, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₇NO₆
M_r	401.44
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.512 (2), 10.402 (1), 14.568 (3)
α, β, γ (°)	109.77 (3), 95.42 (1), 104.41 (2)
V (Å³)	1017.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.26 × 0.24 × 0.21

Data collection
Diffractometer	Nonius MACH3
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.976, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	4471, 3574, 2653
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.129, 1.03
No. of reflections	3574
No. of parameters	268
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

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

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3	0.98	2.36	2.720 (2)	101
N1—H1N···O1ⁱ	0.83 (3)	2.21 (3)	2.995 (2)	160 (3)
C2—H2B···O4ⁱⁱ	0.97	2.55	3.340 (3)	138
C10—H10B···O1ⁱ	0.96	2.59	3.429 (3)	146

Symmetry codes: (i) x−1, y, z; (ii) x−1, y−1, z.

Acknowledgements

VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

Baba, M. (1997). Antivir. Res. 33, 141–152. CrossRef CAS PubMed Web of Science Google Scholar
Baba, M., Okamoto, M., Kawamura, M., Makino, M., Higashida, T., Takashi, T., Kimura, Y., Ikeuchi, T., Tetsuka, T. & Okamoto, T. (1998). Mol. Pharm. 53, 1097–1103. CAS Google Scholar
Baba, M., Okamoto, M., Makino, M., Kimura, Y., Ikeuchi, T., Sakaguchi, T. & Okamoto, T. (1997). Antimicrob. Agents Chemother. 41, 1250–1255. CAS PubMed Web of Science Google Scholar
Davies, D. T., Markwell, R. E., Pearson, N. D. & Takle, A. K. (2005). US Patent 6911442. Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Rose, U. & Draeger, M. (1992). J. Med. Chem. 35, 2238–2243. CSD CrossRef PubMed CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Warrior, P., Heiman, D. F., Fugiel, J. A. & Petracek, P. D. (2005). WO Patent 2005060748. Google Scholar

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

Ethyl 2-methyl-5-oxo-4-(3,4,5-trimeth­­oxy­phen­yl)-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

Ethyl 2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate