Crystal structure of ethyl 2-(2,4,5-tri-meth-oxy-phen-yl)quinoline-4-carboxyl-ate.

In the title compound, C21H21NO5, the dihedral angle between the quinoline ring system (r.m.s. deviation = 0.028 Å) and the tri-meth-oxy-benzene ring is 43.38 (5)°. The C atoms of the meth-oxy 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 intra-molecular C-H⋯O contact closes an S(6) ring. In the crystal, inversion dimers linked by pairs of weak C-H⋯O inter-actions generate R 2 (2)(6) loops. The dimers are linked by further C-H⋯O inter-actions to generate [1-10] chains.

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 ▸).

Experimental

Crystal data

C21H21NO5

M = 367.39

Triclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.117

S = 1.04

3008 reflections

277 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.28 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015011706/hb7449sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

. DOI: 10.1107/S2056989015011706/hb7449fig1.tif

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

CCDC reference: 1407284

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

C21H21NO5	Z = 2
Mr = 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	Dx = 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

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

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(Fo2) + (0.0733P)2 + 0.1234P] where P = (Fo2 + 2Fc2)/3
3008 reflections	(Δ/σ)max < 0.001
277 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C14H14AO4	0.93	2.30	2.9073(18)	123
C9H9AO3i	0.96	2.53	3.397(2)	150
C20H20AO1ii	0.97	2.51	3.304(5)	139

Symmetry codes: (i) ; (ii) .