Crystal structure of ethyl 2-(2,4,5-tri­meth­oxy­phen­yl)quinoline-4-carboxyl­ate

Shrungesh Kumar, T.O.; Naveen, S.; Kumara, M.N.; Mahadevan, K.M.; Lokanath, N.K.

doi:10.1107/S2056989015011706

organic compounds

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o514-o515

doi:10.1107/S2056989015011706

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Crystal structure of ethyl 2-(2,4,5-trimethoxyphenyl)quinoline-4-carboxylate

T. O. Shrungesh Kumar,^a S. Naveen,^b M. N. Kumara,^c K. M. Mahadevan ^a and N. K. Lokanath ^d ^*

^aDepartment of Chemistry, Kuvempu University, Jnanasahyadri, Shankaraghatta 577 451, India, ^bInstitution of Excellence, University of Mysore, Manasagangotri, Mysore 570 006, India, ^cDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India, and ^dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 14 June 2015; accepted 17 June 2015; online 27 June 2015)

In the title compound, C₂₁H₂₁NO₅, the dihedral angle between the quinoline ring system (r.m.s. deviation = 0.028 Å) and the trimethoxybenzene ring is 43.38 (5)°. The C atoms of the methoxy groups deviate from their attached benzene ring by −0.396 (2), −0.049 (2) and 0.192 (2) Å for the ortho-, meta- and para-substituents, respectively. The pendant ethyl chain is disordered over two orientations in a 0.527 (5):0.473 (5) ratio. A short intramolecular C—H⋯O contact closes an S(6) ring. In the crystal, inversion dimers linked by pairs of weak C—H⋯O interactions generate R₂²(6) loops. The dimers are linked by further C—H⋯O interactions to generate [1-10] chains.

Keywords: crystal structure; quinoline; quinolone-4-ethyl carboxylate; hydrogen bonding; C—H⋯O interactions.

CCDC reference: 1407284

1. Related literature

For background to quinolines and their properties, see: Beagley et al. (2003 ). For our work in this area, see: Pradeep et al. (2014 ); Shrungesh Kumar et al. (2015 ); Sunitha et al. (2015 ).

2. Experimental

2.1. Crystal data

C₂₁H₂₁NO₅
M_r = 367.39
Triclinic, $[P \overline 1]$
a = 8.3444 (3) Å
b = 9.3508 (4) Å
c = 12.2723 (5) Å
α = 104.079 (2)°
β = 97.282 (2)°
γ = 93.904 (2)°
V = 916.43 (6) Å³
Z = 2
Cu Kα radiation
μ = 0.78 mm⁻¹
T = 100 K
0.29 × 0.22 × 0.19 mm

2.2. Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.797, T_max = 0.813
10087 measured reflections
3008 independent reflections
2601 reflections with I > 2σ(I)
R_int = 0.041

2.3. Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.117
S = 1.04
3008 reflections
277 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O4	0.93	2.30	2.9073 (18)	123
C9—H9A⋯O3ⁱ	0.96	2.53	3.397 (2)	150
C20—H20A⋯O1ⁱⁱ	0.97	2.51	3.304 (5)	139
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y+1, z.

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: Mercury.

Supporting information

CCDC reference: 1407284

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015011706/hb7449sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015011706/hb7449Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015011706/hb7449Isup3.cml

checkCIF report

Comment top

Quinolines have been found to possess a wide spectrum of biological activities (Beagley et al., 2003,). Among them, the quinolone-4-ethyl carboxylates have been identified as potent antagonizing agents. Keeping in view of their broad spectrum of medicinal properties and in continuation of our work on new quinoline based therapeutic agents (Pradeep et al., 2014, Shrungesh Kumar et al., 2015, Sunitha et al., 2015), the title compound was synthesized. The compound obtained was characterized spectroscopically and its structure was established by X-ray crystallographic studies.

In the title compound, C₂₁H₂₁O₅N, the carboxyl group is disordered. The two rings of the quinoline system are fused almost coaxially, with a dihedral angle between their planes of 2.66°. The dihedral angle between the quinoline ring system mean plane (r.m.s. deviation = 0.0238 Å) and the tri-methoxyphenyl ring is 43.34 (1)°. The structure exhibits both inter and intra-molecular hydrogen bonds of the type C–H···O.

Related literature top

For background to quinolines and their properties, see: Beagley et al. (2003). For our work in this area, see: Pradeep et al. (2014); Shrungesh Kumar et al. (2015); Sunitha et al. (2015).

Experimental top

¹H NMR was recorded at 400 MHz in CDCl₃ solvent. Mass spectra were recorded on a Jeol SX 102=DA-6000 (10 kV) fast atom bombardment (FAB) mass spectrometer.

A mixture of 2-(2,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid 1.0 g (0.005 mol) and absolute EtOH (15 ml) was stirred at 0–5°C. A catalytic amount of concentrated H₂SO₄ was added drop wise into the flask until the powdered 2-(2,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid was dissolved. The solution was then refluxed for 15–17 h. The completion of the reaction was monitored by TLC [hexane and ethyl acetate (9:1 v/v)]. The reaction mixture was poured into a crushed ice (100 ml). The precipitate was collected by filtration, washed with water and EtOH, dried under vacuum to obtain the crude product in 85% yield. The crude product was purified by column chromatography using silica gel (60–120 mesh, petroleum ether: ethyl acetate, 9:1 v/v). Colourless rectangular crystals grew after 4 days due to slow evaporation of the solvent. Yield = 85%. M·P. = 100–102 °C.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

Figures top

Fig. 1. A view of the title molecule, with displacement ellipsoids drawn at the 50% probability level.

Ethyl 2-(2,4,5-trimethoxyphenyl)quinoline-4-carboxylate top

Crystal data top

C₂₁H₂₁NO₅	Z = 2
M_r = 367.39	F(000) = 388
Triclinic, P1	¹H NMR(400 MHz, CdCl₃ ): δ = 8.71 (d, J = 8.40 Hz, 1H), 8.52 (s, 1H), 7.76 (t, J = 7.60 Hz, 1H), 7.63 (t, J = 6.00 Hz, 2H), 7.25 (s, 1H), 6.64 (s, 1H), 4.52 (q, J = 6.80 Hz, 2H), 3.97 (d, J = 5.20 Hz, 6H), 3.88 (s, 3H), 1.47 (t, J = 7.20 Hz, 3H) ppm. MS (70 eV) m/z(%): 368.0(M⁺).
Hall symbol: -P 1	D_x = 1.331 Mg m⁻³
a = 8.3444 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 9.3508 (4) Å	Cell parameters from 2601 reflections
c = 12.2723 (5) Å	θ = 6.9–64.4°
α = 104.079 (2)°	µ = 0.78 mm⁻¹
β = 97.282 (2)°	T = 100 K
γ = 93.904 (2)°	Rectangular block, colourless
V = 916.43 (6) Å³	0.29 × 0.22 × 0.19 mm

Data collection top

Bruker X8 Proteum diffractometer	3008 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2601 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.041
Detector resolution: 18.4 pixels mm^-1	θ_max = 64.4°, θ_min = 6.9°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −10→10
T_min = 0.797, T_max = 0.813	l = −14→14
10087 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0733P)² + 0.1234P] where P = (F_o² + 2F_c²)/3
3008 reflections	(Δ/σ)_max < 0.001
277 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₁H₂₁NO₅	γ = 93.904 (2)°
M_r = 367.39	V = 916.43 (6) Å³
Triclinic, P1	Z = 2
a = 8.3444 (3) Å	Cu Kα radiation
b = 9.3508 (4) Å	µ = 0.78 mm⁻¹
c = 12.2723 (5) Å	T = 100 K
α = 104.079 (2)°	0.29 × 0.22 × 0.19 mm
β = 97.282 (2)°

Data collection top

Bruker X8 Proteum diffractometer	3008 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	2601 reflections with I > 2σ(I)
T_min = 0.797, T_max = 0.813	R_int = 0.041
10087 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.20 e Å⁻³
3008 reflections	Δρ_min = −0.28 e Å⁻³
277 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	Occ. (<1)
O1	0.85573 (12)	−0.06460 (10)	0.25750 (8)	0.0282 (3)
O2	0.82233 (13)	−0.11123 (10)	0.03839 (8)	0.0292 (3)
O3	0.55682 (13)	0.33976 (11)	0.05983 (8)	0.0315 (4)
O4	0.22604 (13)	0.74517 (12)	0.41032 (9)	0.0388 (3)
O5	0.1869 (4)	0.5760 (4)	0.2445 (2)	0.0279 (8)	0.527 (5)
N1	0.73685 (14)	0.47119 (12)	0.39148 (9)	0.0220 (3)
C1	0.73786 (16)	0.17037 (14)	0.27663 (12)	0.0211 (4)
C2	0.78484 (16)	0.04140 (15)	0.21340 (12)	0.0215 (4)
C3	0.76438 (16)	0.01469 (15)	0.09451 (12)	0.0228 (4)
C4	0.68822 (17)	0.11314 (15)	0.04271 (12)	0.0247 (4)
C5	0.63437 (16)	0.24009 (15)	0.10755 (12)	0.0226 (4)
C6	0.66258 (16)	0.27241 (14)	0.22587 (12)	0.0203 (4)
C7	0.8450 (2)	−0.05532 (17)	0.37384 (13)	0.0361 (5)
C8	0.81347 (19)	−0.13690 (17)	−0.08181 (12)	0.0315 (5)
C9	0.5312 (2)	0.31046 (18)	−0.06125 (12)	0.0370 (5)
C10	0.62512 (16)	0.41161 (14)	0.30220 (11)	0.0204 (4)
C11	0.47701 (17)	0.47445 (15)	0.28373 (12)	0.0222 (4)
C12	0.44526 (17)	0.59953 (14)	0.35868 (11)	0.0218 (4)
C13	0.56525 (16)	0.67030 (14)	0.45409 (12)	0.0222 (4)
C14	0.55434 (18)	0.80529 (15)	0.53426 (12)	0.0257 (4)
C15	0.67839 (19)	0.86451 (16)	0.62120 (13)	0.0296 (4)
C16	0.81946 (18)	0.79239 (17)	0.63317 (13)	0.0295 (5)
C17	0.83567 (18)	0.66226 (16)	0.55755 (12)	0.0263 (4)
C18	0.70992 (16)	0.59871 (14)	0.46574 (11)	0.0215 (4)
C19	0.28323 (18)	0.65885 (16)	0.34077 (12)	0.0282 (4)
C20	0.0230 (6)	0.6201 (5)	0.2213 (3)	0.0326 (12)	0.527 (5)
C21	−0.0515 (4)	0.5296 (4)	0.1068 (3)	0.0495 (13)	0.527 (5)
C20X	0.0784 (5)	0.6858 (5)	0.1962 (3)	0.0279 (11)	0.473 (5)
C21X	−0.0638 (6)	0.5817 (5)	0.2021 (4)	0.0389 (14)	0.473 (5)
O5X	0.2315 (4)	0.6296 (4)	0.2276 (3)	0.0255 (9)	0.473 (5)
H7A	0.89180	−0.13750	0.39500	0.0540*
H7C	0.90300	0.03580	0.42020	0.0540*
H8A	0.86270	−0.22540	−0.11110	0.0470*
H7B	0.73310	−0.05810	0.38480	0.0540*
H1A	0.75670	0.19040	0.35550	0.0250*
H4A	0.67280	0.09450	−0.03610	0.0300*
H9B	0.46750	0.21660	−0.09300	0.0550*
H9C	0.63410	0.30780	−0.08850	0.0550*
H11A	0.40110	0.43010	0.22010	0.0270*
H14A	0.46170	0.85430	0.52770	0.0310*
H15A	0.66930	0.95350	0.67290	0.0360*
H16A	0.90240	0.83360	0.69310	0.0350*
H17A	0.92940	0.61520	0.56630	0.0320*
H20A	0.02880	0.72470	0.22330	0.0390*	0.527 (5)
H20B	−0.04160	0.60270	0.27810	0.0390*	0.527 (5)
H21A	−0.15830	0.55740	0.08850	0.0740*	0.527 (5)
H21B	−0.05870	0.42660	0.10630	0.0740*	0.527 (5)
H21C	0.01440	0.54650	0.05150	0.0740*	0.527 (5)
H8B	0.87000	−0.05420	−0.09920	0.0470*
H8C	0.70180	−0.14830	−0.11600	0.0470*
H9A	0.47470	0.38730	−0.08350	0.0550*
H20C	0.07290	0.69820	0.11960	0.0330*	0.473 (5)
H20D	0.07340	0.78210	0.24710	0.0330*	0.473 (5)
H21D	−0.16300	0.61860	0.17740	0.0580*	0.473 (5)
H21E	−0.06240	0.57460	0.27900	0.0580*	0.473 (5)
H21F	−0.05690	0.48550	0.15380	0.0580*	0.473 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0405 (6)	0.0247 (5)	0.0224 (6)	0.0145 (4)	0.0067 (5)	0.0076 (4)
O2	0.0396 (6)	0.0251 (5)	0.0220 (6)	0.0129 (4)	0.0073 (4)	0.0004 (4)
O3	0.0467 (7)	0.0290 (6)	0.0194 (6)	0.0160 (5)	0.0014 (5)	0.0060 (4)
O4	0.0359 (6)	0.0413 (6)	0.0347 (6)	0.0193 (5)	0.0053 (5)	−0.0032 (5)
O5	0.0231 (14)	0.0331 (16)	0.0269 (14)	0.0105 (11)	0.0050 (10)	0.0040 (11)
N1	0.0230 (6)	0.0229 (6)	0.0196 (6)	0.0028 (5)	0.0038 (5)	0.0040 (5)
C1	0.0213 (7)	0.0225 (7)	0.0198 (7)	0.0027 (5)	0.0045 (6)	0.0050 (6)
C2	0.0209 (7)	0.0214 (7)	0.0228 (7)	0.0042 (5)	0.0029 (6)	0.0067 (6)
C3	0.0233 (7)	0.0207 (7)	0.0228 (8)	0.0031 (5)	0.0053 (6)	0.0012 (6)
C4	0.0283 (8)	0.0266 (7)	0.0180 (7)	0.0038 (6)	0.0031 (6)	0.0036 (6)
C5	0.0229 (7)	0.0233 (7)	0.0219 (8)	0.0042 (5)	0.0021 (6)	0.0066 (6)
C6	0.0180 (6)	0.0220 (7)	0.0212 (7)	0.0023 (5)	0.0038 (5)	0.0055 (6)
C7	0.0576 (11)	0.0295 (8)	0.0277 (9)	0.0165 (7)	0.0121 (8)	0.0134 (7)
C8	0.0379 (9)	0.0317 (8)	0.0214 (8)	0.0095 (6)	0.0070 (6)	−0.0027 (6)
C9	0.0579 (11)	0.0331 (8)	0.0196 (8)	0.0135 (7)	−0.0025 (7)	0.0080 (7)
C10	0.0227 (7)	0.0215 (7)	0.0194 (7)	0.0034 (5)	0.0059 (6)	0.0082 (6)
C11	0.0239 (7)	0.0237 (7)	0.0193 (7)	0.0039 (5)	0.0033 (6)	0.0057 (6)
C12	0.0256 (7)	0.0219 (7)	0.0206 (7)	0.0054 (5)	0.0067 (6)	0.0083 (6)
C13	0.0261 (7)	0.0213 (7)	0.0211 (7)	0.0016 (5)	0.0086 (6)	0.0069 (6)
C14	0.0294 (8)	0.0236 (7)	0.0257 (8)	0.0046 (6)	0.0105 (6)	0.0054 (6)
C15	0.0375 (8)	0.0231 (7)	0.0258 (8)	−0.0009 (6)	0.0124 (7)	−0.0014 (6)
C16	0.0295 (8)	0.0333 (8)	0.0220 (8)	−0.0044 (6)	0.0054 (6)	0.0011 (6)
C17	0.0247 (7)	0.0309 (8)	0.0220 (8)	0.0018 (6)	0.0053 (6)	0.0036 (6)
C18	0.0249 (7)	0.0214 (7)	0.0194 (7)	0.0015 (5)	0.0079 (6)	0.0056 (6)
C19	0.0323 (8)	0.0288 (7)	0.0239 (8)	0.0113 (6)	0.0050 (6)	0.0046 (6)
C20	0.022 (2)	0.035 (2)	0.042 (2)	0.0086 (18)	0.0069 (19)	0.0095 (17)
C21	0.0295 (18)	0.057 (2)	0.052 (3)	0.0140 (15)	−0.0062 (16)	−0.0014 (19)
C20X	0.0195 (18)	0.034 (2)	0.033 (2)	0.0086 (15)	0.0046 (14)	0.0120 (16)
C21X	0.024 (2)	0.042 (2)	0.050 (3)	−0.0030 (19)	0.010 (2)	0.010 (2)
O5X	0.0205 (15)	0.0359 (18)	0.0222 (14)	0.0111 (12)	0.0051 (11)	0.0084 (12)

Geometric parameters (Å, º) top

O1—C2	1.3729 (17)	C17—C18	1.419 (2)
O1—C7	1.4238 (18)	C20—C21	1.485 (5)
O2—C3	1.3645 (17)	C20X—C21X	1.503 (7)
O2—C8	1.4272 (17)	C1—H1A	0.9300
O3—C5	1.3718 (18)	C4—H4A	0.9300
O3—C9	1.4291 (17)	C7—H7A	0.9600
O4—C19	1.1951 (18)	C7—H7B	0.9600
O5—C19	1.368 (3)	C7—H7C	0.9600
O5—C20	1.469 (6)	C8—H8A	0.9600
O5X—C20X	1.457 (6)	C8—H8B	0.9600
O5X—C19	1.355 (4)	C8—H8C	0.9600
N1—C18	1.3648 (17)	C9—H9A	0.9600
N1—C10	1.3242 (17)	C9—H9B	0.9600
C1—C2	1.377 (2)	C9—H9C	0.9600
C1—C6	1.4017 (19)	C11—H11A	0.9300
C2—C3	1.405 (2)	C14—H14A	0.9300
C3—C4	1.385 (2)	C15—H15A	0.9300
C4—C5	1.396 (2)	C16—H16A	0.9300
C5—C6	1.395 (2)	C17—H17A	0.9300
C6—C10	1.4852 (19)	C20—H20A	0.9700
C10—C11	1.420 (2)	C20—H20B	0.9700
C11—C12	1.366 (2)	C20X—H20C	0.9700
C12—C19	1.507 (2)	C20X—H20D	0.9700
C12—C13	1.4307 (19)	C21—H21C	0.9600
C13—C18	1.4278 (19)	C21—H21A	0.9600
C13—C14	1.416 (2)	C21—H21B	0.9600
C14—C15	1.368 (2)	C21X—H21D	0.9600
C15—C16	1.405 (2)	C21X—H21E	0.9600
C16—C17	1.366 (2)	C21X—H21F	0.9600

C2—O1—C7	115.97 (11)	O1—C7—H7B	109.00
C3—O2—C8	117.06 (11)	O1—C7—H7C	109.00
C5—O3—C9	117.82 (12)	H7A—C7—H7B	109.00
C19—O5—C20	116.5 (3)	H7A—C7—H7C	109.00
C19—O5X—C20X	115.2 (3)	H7B—C7—H7C	110.00
C10—N1—C18	118.72 (12)	O2—C8—H8A	109.00
C2—C1—C6	122.04 (13)	O2—C8—H8B	109.00
O1—C2—C1	125.03 (13)	O2—C8—H8C	109.00
O1—C2—C3	115.89 (12)	H8A—C8—H8B	109.00
C1—C2—C3	119.05 (13)	H8A—C8—H8C	110.00
O2—C3—C2	115.51 (12)	H8B—C8—H8C	109.00
O2—C3—C4	124.83 (13)	O3—C9—H9A	109.00
C2—C3—C4	119.66 (13)	O3—C9—H9B	109.00
C3—C4—C5	120.65 (13)	O3—C9—H9C	109.00
O3—C5—C6	117.12 (12)	H9A—C9—H9B	109.00
C4—C5—C6	120.22 (13)	H9A—C9—H9C	109.00
O3—C5—C4	122.64 (12)	H9B—C9—H9C	110.00
C1—C6—C5	118.19 (13)	C10—C11—H11A	120.00
C5—C6—C10	124.27 (12)	C12—C11—H11A	120.00
C1—C6—C10	117.48 (12)	C13—C14—H14A	120.00
N1—C10—C6	115.55 (12)	C15—C14—H14A	120.00
C6—C10—C11	122.60 (12)	C14—C15—H15A	120.00
N1—C10—C11	121.81 (12)	C16—C15—H15A	120.00
C10—C11—C12	120.52 (13)	C15—C16—H16A	120.00
C11—C12—C13	119.41 (13)	C17—C16—H16A	120.00
C13—C12—C19	121.15 (12)	C16—C17—H17A	120.00
C11—C12—C19	119.44 (12)	C18—C17—H17A	120.00
C12—C13—C14	125.81 (13)	O5—C20—H20A	110.00
C14—C13—C18	118.19 (12)	O5—C20—H20B	110.00
C12—C13—C18	115.97 (12)	C21—C20—H20A	110.00
C13—C14—C15	120.82 (14)	C21—C20—H20B	110.00
C14—C15—C16	120.71 (14)	H20A—C20—H20B	109.00
C15—C16—C17	120.52 (14)	O5X—C20X—H20D	109.00
C16—C17—C18	120.16 (14)	C21X—C20X—H20C	109.00
N1—C18—C13	123.51 (12)	C21X—C20X—H20D	109.00
N1—C18—C17	116.89 (12)	H20C—C20X—H20D	108.00
C13—C18—C17	119.59 (12)	O5X—C20X—H20C	109.00
O4—C19—C12	126.01 (13)	H21A—C21—H21C	109.00
O4—C19—O5X	123.5 (2)	H21B—C21—H21C	110.00
O4—C19—O5	120.22 (19)	C20—C21—H21A	109.00
O5X—C19—C12	108.59 (18)	C20—C21—H21B	109.00
O5—C19—C12	111.91 (18)	C20—C21—H21C	109.00
O5—C20—C21	107.5 (3)	H21A—C21—H21B	110.00
O5X—C20X—C21X	111.1 (4)	C20X—C21X—H21D	109.00
C2—C1—H1A	119.00	C20X—C21X—H21E	109.00
C6—C1—H1A	119.00	C20X—C21X—H21F	110.00
C3—C4—H4A	120.00	H21D—C21X—H21E	109.00
C5—C4—H4A	120.00	H21D—C21X—H21F	109.00
O1—C7—H7A	109.00	H21E—C21X—H21F	109.00

C7—O1—C2—C1	14.91 (19)	C4—C5—C6—C10	173.60 (13)
C7—O1—C2—C3	−166.87 (12)	C1—C6—C10—N1	39.18 (18)
C8—O2—C3—C2	−175.94 (12)	C1—C6—C10—C11	−138.53 (14)
C8—O2—C3—C4	4.6 (2)	C5—C6—C10—N1	−137.83 (14)
C9—O3—C5—C4	0.0 (2)	C5—C6—C10—C11	44.5 (2)
C9—O3—C5—C6	178.22 (13)	N1—C10—C11—C12	−0.1 (2)
C20—O5—C19—O4	12.1 (4)	C6—C10—C11—C12	177.43 (13)
C20—O5—C19—C12	177.4 (3)	C10—C11—C12—C13	2.3 (2)
C19—O5—C20—C21	172.6 (3)	C10—C11—C12—C19	−176.45 (13)
C18—N1—C10—C6	−179.53 (12)	C11—C12—C13—C14	175.50 (14)
C18—N1—C10—C11	−1.8 (2)	C11—C12—C13—C18	−2.47 (19)
C10—N1—C18—C13	1.6 (2)	C19—C12—C13—C14	−5.7 (2)
C10—N1—C18—C17	−177.38 (13)	C19—C12—C13—C18	176.29 (12)
C6—C1—C2—O1	−178.50 (13)	C11—C12—C19—O4	162.65 (15)
C6—C1—C2—C3	3.3 (2)	C11—C12—C19—O5	−1.7 (2)
C2—C1—C6—C5	0.4 (2)	C13—C12—C19—O4	−16.1 (2)
C2—C1—C6—C10	−176.77 (13)	C13—C12—C19—O5	179.57 (19)
O1—C2—C3—O2	−1.94 (18)	C12—C13—C14—C15	−178.64 (14)
O1—C2—C3—C4	177.53 (12)	C18—C13—C14—C15	−0.7 (2)
C1—C2—C3—O2	176.39 (12)	C12—C13—C18—N1	0.6 (2)
C1—C2—C3—C4	−4.1 (2)	C12—C13—C18—C17	179.48 (13)
O2—C3—C4—C5	−179.35 (13)	C14—C13—C18—N1	−177.57 (13)
C2—C3—C4—C5	1.2 (2)	C14—C13—C18—C17	1.4 (2)
C3—C4—C5—O3	−179.28 (13)	C13—C14—C15—C16	−0.2 (2)
C3—C4—C5—C6	2.6 (2)	C14—C15—C16—C17	0.5 (2)
O3—C5—C6—C1	178.38 (12)	C15—C16—C17—C18	0.2 (2)
O3—C5—C6—C10	−4.6 (2)	C16—C17—C18—N1	177.90 (13)
C4—C5—C6—C1	−3.4 (2)	C16—C17—C18—C13	−1.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O4	0.93	2.30	2.9073 (18)	123
C9—H9A···O3ⁱ	0.96	2.53	3.397 (2)	150
C20—H20A···O1ⁱⁱ	0.97	2.51	3.304 (5)	139

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O4	0.93	2.30	2.9073 (18)	123
C9—H9A···O3ⁱ	0.96	2.53	3.397 (2)	150
C20—H20A···O1ⁱⁱ	0.97	2.51	3.304 (5)	139

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

Acknowledgements

The authors are thankful to the IOE, Vijnana Bhavana, University of Mysore, Mysore, for providing the single-crystal X-ray diffractometer facility.

References

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Volume 71| Part 7| July 2015| Pages o514-o515

doi:10.1107/S2056989015011706

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

Crystal structure of ethyl 2-(2,4,5-tri­meth­­oxy­phen­yl)quinoline-4-carboxyl­ate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of ethyl 2-(2,4,5-trimethoxyphenyl)quinoline-4-carboxylate