Crystal structure of ethyl 6-bromo-2-[(E)-2-phenyl­ethen­yl]quinoline-4-carboxyl­ate

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

doi:10.1107/S2056989014028266

organic compounds

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Volume 71| Part 2| February 2015| Page o121

doi:10.1107/S2056989014028266

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Crystal structure of ethyl 6-bromo-2-[(E)-2-phenylethenyl]quinoline-4-carboxylate

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

^aDepartment of Chemistry, Kuvempu University, Jnanasahyadri, Shankaraghatta 577 451, India, ^bInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, ^cDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysuru 570 005, India, ^dDepartment of Chemistry, Kuvempu University, Jnanasahyadri, Shankaraghatta 577451, India, and ^eDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India
^*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 10 December 2014; accepted 31 December 2014; online 17 January 2015)

In the title compound, C₂₀H₁₆BrNO₂, the dihedral angle between the quinolone ring system mean plane (r.m.s. deviation = 0.018 Å) and the phenyl ring bridged by the ethynyl group, is 25.44 (14)°. There is an intramolecular C—H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, molecules are linked via C—H⋯O hydrogen bonds forming chains propagating along the b-axis direction.

Keywords: crystal structure; quinoline; quinoline-4-carboxylate; hydrogen bonding.

CCDC reference: 1041593

1. Related literature

For pharmaceutical and pharmacological activities of quinolines, see: Beagley et al. (2003 ). The title compound was synthesized in a continuation of our work on new quinoline-based therapeutic agents, see: Pradeep et al. (2014 ).

2. Experimental

2.1. Crystal data

C₂₀H₁₆BrNO₂
M_r = 382.24
Orthorhombic, P b c a
a = 14.0819 (7) Å
b = 9.7470 (5) Å
c = 24.0399 (12) Å
V = 3299.6 (3) Å³
Z = 8
Cu Kα radiation
μ = 3.49 mm⁻¹
T = 293 K
0.30 × 0.27 × 0.25 mm

2.2. Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.421, T_max = 0.476
12970 measured reflections
2722 independent reflections
2213 reflections with I > 2σ(I)
R_int = 0.071

2.3. Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.134
S = 1.04
2722 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O13	0.93	2.22	2.848 (4)	124
C15—H15A⋯O13ⁱ	0.97	2.51	3.413 (4)	154
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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: SHELXL97.

Supporting information

CCDC reference: 1041593

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989014028266/su5042sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989014028266/su5042Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989014028266/su5042Isup3.cml

checkCIF report

Comment top

Quinolines have been considered as the most prevalent N-hetero aromatic compounds that exhibit a wide spectrum of pharmaceutical and pharmacological activities (Beagley et al., 2003). Some of the quinoline-4-carboxylates were reported to possess potent 5HT₃ antagonizing activity and anti-emetic activity. 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), the title compound was synthesized, and we report herein on its crystal structure.

The molecular structure of the title molecule is shown in Fig. 1. The quinoline ring system (N1/C2-C10) is planar with the maximum deviations from the mean plane being for atoms C8 and C5 viz. 0.018 (2) Å. The dihedral angle between the quinoline ring and the phenyl ring (C19–C24) bridged by the ethynyl group is 25.44 (14)°. The two rings of the quinolyl moiety are fused in an axial fashion and form a dihedral angle of 1.15 (13)°.

In the crystal, molecules are linked via C–H···O hydrogen bonds forming chains propagating along the b axis direction (Table 1 and Fig. 2).

Related literature top

For pharmaceutical and pharmacological activities of quinolines, see: Beagley et al. (2003). The title compound was synthesized in a continuation of our work on new quinoline-based therapeutic agents, see: Pradeep et al. (2014).

Experimental top

A mixture of 2-aryl-6-chloro/bromo quinoline-4-carboxylic acid (1.0 g) and absolute EtOH (15 ml) was stirred at 273 - 278 K. The concentrated sulfuric acid (2 - 3 ml) was added drop wise into the flask until the powdered 2-aryl-6-chloroquinoline-4-carboxylic acid was completely dissolved. The solution was then refluxed for 15–17 h. The completion of the reaction was monitored by thin layer chromatography [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 afford crude product. The crude product was purified by column chromatography using silica gel (60–120 mesh, petroleum ether: ethyl acetate, 9:1 v/v). Green block-shaped crystals were obtained by slow evaporation of the solvent.

¹H-NMR(400 MHz, CDCl₃): δ = 8.95 (d, J = 2.00 Hz, 1H), 8.17 (s, 1H), 7.99 (d, J = 4.40 Hz, 1H), 7.82 (d, J = 2.40 Hz, 1H), 7.81 (t, J = 2.00 Hz, 1H), 7.75 (s, 1H), 7.65 (d, J = 7.20 Hz, 1H), 7.35–7.35 (m, 4H), 4.54 (q, J = 7.20 Hz, 2H), 1.46–1.49 (m, 3H) p.p.m.. MS (70 eV) m/z (%): 382.0 (M⁺).

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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular hydrogen bond is shown as dashed line (see Table 1 for details).
	Fig. 2. A partial view along the a axis of the crystal packing of the title compound. The intra- and inter-molecular hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms: grey balls; H atoms not involved in hydrogen bonding have been omitted for clarity).

Ethyl 6-bromo-2-[(E)-2-phenylethenyl]quinoline-4-carboxylate top

Crystal data top

C₂₀H₁₆BrNO₂	F(000) = 1552
M_r = 382.24	D_x = 1.539 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2722 reflections
a = 14.0819 (7) Å	θ = 5.8–64.5°
b = 9.7470 (5) Å	µ = 3.49 mm⁻¹
c = 24.0399 (12) Å	T = 293 K
V = 3299.6 (3) Å³	Block, green
Z = 8	0.30 × 0.27 × 0.25 mm

Data collection top

Bruker X8 Proteum diffractometer	2722 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2213 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.071
Detector resolution: 18.4 pixels mm^-1	θ_max = 64.5°, θ_min = 5.8°
ϕ and ω scans	h = −16→15
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −11→11
T_min = 0.421, T_max = 0.476	l = −28→27
12970 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0857P)²] where P = (F_o² + 2F_c²)/3
2722 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.78 e Å⁻³
0 restraints	Δρ_min = −0.92 e Å⁻³

Crystal data top

C₂₀H₁₆BrNO₂	V = 3299.6 (3) Å³
M_r = 382.24	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 14.0819 (7) Å	µ = 3.49 mm⁻¹
b = 9.7470 (5) Å	T = 293 K
c = 24.0399 (12) Å	0.30 × 0.27 × 0.25 mm

Data collection top

Bruker X8 Proteum diffractometer	2722 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	2213 reflections with I > 2σ(I)
T_min = 0.421, T_max = 0.476	R_int = 0.071
12970 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.04	Δρ_max = 0.78 e Å⁻³
2722 reflections	Δρ_min = −0.92 e Å⁻³
218 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
Br11	0.40232 (3)	0.12926 (3)	0.45926 (2)	0.0260 (2)
O13	0.3502 (2)	0.6096 (2)	0.39081 (10)	0.0299 (8)
O14	0.32650 (17)	0.8275 (2)	0.41637 (9)	0.0225 (7)
N1	0.3740 (2)	0.6330 (3)	0.60400 (12)	0.0194 (9)
C2	0.3819 (2)	0.5243 (3)	0.56849 (15)	0.0186 (9)
C3	0.4009 (2)	0.3948 (4)	0.59271 (17)	0.0235 (11)
C4	0.4086 (2)	0.2801 (4)	0.56073 (17)	0.0252 (11)
C5	0.3971 (2)	0.2916 (3)	0.50306 (16)	0.0212 (10)
C6	0.3799 (2)	0.4140 (3)	0.47707 (15)	0.0186 (10)
C7	0.3720 (2)	0.5345 (3)	0.50974 (14)	0.0169 (9)
C8	0.3536 (2)	0.6688 (3)	0.48784 (14)	0.0170 (9)
C9	0.3445 (2)	0.7753 (3)	0.52462 (14)	0.0194 (10)
C10	0.3557 (2)	0.7552 (3)	0.58248 (14)	0.0183 (9)
C12	0.3436 (2)	0.6941 (3)	0.42679 (14)	0.0191 (10)
C15	0.3129 (3)	0.8638 (3)	0.35775 (15)	0.0256 (11)
C16	0.4064 (3)	0.8926 (4)	0.33011 (17)	0.0305 (11)
C17	0.3493 (2)	0.8754 (3)	0.61965 (15)	0.0208 (10)
C18	0.3704 (3)	0.8739 (3)	0.67333 (15)	0.0208 (11)
C19	0.3718 (2)	0.9924 (3)	0.71107 (14)	0.0189 (9)
C20	0.3281 (3)	1.1179 (3)	0.69823 (15)	0.0237 (11)
C21	0.3389 (3)	1.2296 (3)	0.73304 (16)	0.0251 (10)
C22	0.3913 (2)	1.2187 (4)	0.78153 (15)	0.0237 (11)
C23	0.4324 (3)	1.0941 (4)	0.79619 (15)	0.0246 (10)
C24	0.4218 (3)	0.9823 (3)	0.76129 (14)	0.0216 (10)
H3	0.40820	0.38790	0.63110	0.0280*
H4	0.42130	0.19540	0.57690	0.0300*
H6	0.37340	0.41800	0.43860	0.0220*
H9	0.33080	0.86260	0.51130	0.0230*
H15A	0.27260	0.94430	0.35520	0.0310*
H15B	0.28130	0.78890	0.33870	0.0310*
H16A	0.43890	0.96390	0.35000	0.0460*
H16B	0.39560	0.92140	0.29240	0.0460*
H16C	0.44440	0.81090	0.33020	0.0460*
H17	0.32900	0.95800	0.60430	0.0250*
H18	0.38580	0.78920	0.68870	0.0250*
H20	0.29170	1.12590	0.66610	0.0280*
H21	0.31060	1.31280	0.72380	0.0300*
H22	0.39920	1.29490	0.80430	0.0290*
H23	0.46650	1.08590	0.82910	0.0300*
H24	0.44850	0.89860	0.77140	0.0260*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br11	0.0262 (3)	0.0137 (3)	0.0382 (3)	0.0007 (1)	−0.0011 (2)	−0.0051 (1)
O13	0.0497 (17)	0.0187 (12)	0.0212 (14)	−0.0009 (11)	0.0006 (12)	−0.0020 (10)
O14	0.0314 (13)	0.0173 (11)	0.0189 (12)	0.0030 (10)	0.0002 (10)	0.0021 (10)
N1	0.0182 (14)	0.0181 (15)	0.0218 (16)	−0.0046 (10)	0.0005 (12)	−0.0002 (11)
C2	0.0163 (15)	0.0166 (16)	0.0229 (18)	−0.0042 (13)	0.0002 (14)	0.0001 (14)
C3	0.026 (2)	0.0204 (18)	0.024 (2)	−0.0024 (13)	−0.0019 (14)	0.0032 (15)
C4	0.0229 (19)	0.0166 (18)	0.036 (2)	−0.0019 (13)	−0.0029 (15)	0.0059 (16)
C5	0.0158 (17)	0.0159 (17)	0.032 (2)	−0.0005 (12)	0.0000 (13)	−0.0022 (15)
C6	0.0162 (16)	0.0160 (16)	0.0236 (18)	−0.0038 (13)	0.0008 (14)	−0.0003 (14)
C7	0.0136 (15)	0.0133 (16)	0.0239 (18)	−0.0019 (13)	0.0010 (13)	−0.0003 (13)
C8	0.0140 (15)	0.0157 (15)	0.0213 (18)	−0.0035 (13)	−0.0005 (13)	−0.0023 (13)
C9	0.0208 (17)	0.0154 (16)	0.0220 (18)	−0.0019 (13)	−0.0015 (14)	−0.0006 (13)
C10	0.0157 (16)	0.0182 (16)	0.0211 (17)	−0.0029 (13)	−0.0004 (13)	0.0018 (13)
C12	0.0202 (17)	0.0158 (15)	0.0212 (18)	−0.0003 (13)	0.0009 (13)	−0.0006 (14)
C15	0.032 (2)	0.0246 (18)	0.0201 (19)	0.0066 (14)	−0.0022 (15)	0.0029 (14)
C16	0.043 (2)	0.0216 (18)	0.027 (2)	−0.0002 (15)	0.0061 (16)	0.0010 (16)
C17	0.0218 (17)	0.0154 (16)	0.0253 (19)	−0.0014 (13)	0.0009 (14)	−0.0010 (13)
C18	0.0209 (18)	0.0174 (17)	0.024 (2)	−0.0010 (13)	0.0021 (14)	0.0001 (13)
C19	0.0180 (15)	0.0179 (15)	0.0207 (17)	−0.0031 (13)	0.0030 (14)	−0.0007 (14)
C20	0.0236 (19)	0.0276 (18)	0.0200 (19)	0.0020 (14)	−0.0020 (14)	−0.0011 (14)
C21	0.0296 (19)	0.0190 (16)	0.0267 (19)	0.0063 (14)	0.0016 (15)	0.0004 (15)
C22	0.0267 (19)	0.0232 (17)	0.0213 (19)	−0.0062 (14)	0.0043 (14)	−0.0063 (14)
C23	0.0257 (18)	0.0279 (17)	0.0203 (18)	−0.0015 (15)	−0.0031 (15)	0.0007 (15)
C24	0.0264 (18)	0.0189 (16)	0.0194 (17)	0.0016 (14)	0.0007 (14)	0.0039 (14)

Geometric parameters (Å, º) top

Br11—C5	1.902 (3)	C19—C24	1.401 (5)
O13—C12	1.198 (4)	C20—C21	1.382 (5)
O14—C12	1.346 (4)	C21—C22	1.384 (5)
O14—C15	1.466 (4)	C22—C23	1.391 (5)
N1—C2	1.365 (4)	C23—C24	1.383 (5)
N1—C10	1.324 (4)	C3—H3	0.9300
C2—C3	1.416 (5)	C4—H4	0.9300
C2—C7	1.423 (5)	C6—H6	0.9300
C3—C4	1.361 (6)	C9—H9	0.9300
C4—C5	1.400 (6)	C15—H15A	0.9700
C5—C6	1.368 (4)	C15—H15B	0.9700
C6—C7	1.417 (4)	C16—H16A	0.9600
C7—C8	1.435 (4)	C16—H16B	0.9600
C8—C9	1.370 (4)	C16—H16C	0.9600
C8—C12	1.495 (5)	C17—H17	0.9300
C9—C10	1.414 (5)	C18—H18	0.9300
C10—C17	1.476 (4)	C20—H20	0.9300
C15—C16	1.501 (6)	C21—H21	0.9300
C17—C18	1.324 (5)	C22—H22	0.9300
C18—C19	1.469 (4)	C23—H23	0.9300
C19—C20	1.404 (4)	C24—H24	0.9300

C12—O14—C15	115.8 (2)	C19—C24—C23	121.4 (3)
C2—N1—C10	118.0 (3)	C2—C3—H3	120.00
N1—C2—C3	116.8 (3)	C4—C3—H3	119.00
N1—C2—C7	124.0 (3)	C3—C4—H4	121.00
C3—C2—C7	119.3 (3)	C5—C4—H4	120.00
C2—C3—C4	121.0 (4)	C5—C6—H6	121.00
C3—C4—C5	119.0 (3)	C7—C6—H6	121.00
Br11—C5—C4	118.5 (2)	C8—C9—H9	119.00
Br11—C5—C6	118.6 (3)	C10—C9—H9	119.00
C4—C5—C6	122.8 (3)	O14—C15—H15A	109.00
C5—C6—C7	118.9 (3)	O14—C15—H15B	109.00
C2—C7—C6	119.0 (3)	C16—C15—H15A	109.00
C2—C7—C8	116.5 (3)	C16—C15—H15B	110.00
C6—C7—C8	124.5 (3)	H15A—C15—H15B	108.00
C7—C8—C9	118.1 (3)	C15—C16—H16A	109.00
C7—C8—C12	121.9 (3)	C15—C16—H16B	109.00
C9—C8—C12	120.0 (3)	C15—C16—H16C	109.00
C8—C9—C10	121.3 (3)	H16A—C16—H16B	110.00
N1—C10—C9	122.1 (3)	H16A—C16—H16C	110.00
N1—C10—C17	119.3 (3)	H16B—C16—H16C	109.00
C9—C10—C17	118.6 (3)	C10—C17—H17	118.00
O13—C12—O14	122.9 (3)	C18—C17—H17	118.00
O13—C12—C8	126.0 (3)	C17—C18—H18	117.00
O14—C12—C8	111.0 (3)	C19—C18—H18	117.00
O14—C15—C16	110.9 (3)	C19—C20—H20	120.00
C10—C17—C18	124.6 (3)	C21—C20—H20	120.00
C17—C18—C19	126.6 (3)	C20—C21—H21	120.00
C18—C19—C20	122.9 (3)	C22—C21—H21	120.00
C18—C19—C24	118.9 (3)	C21—C22—H22	120.00
C20—C19—C24	118.1 (3)	C23—C22—H22	120.00
C19—C20—C21	120.4 (3)	C22—C23—H23	120.00
C20—C21—C22	120.6 (3)	C24—C23—H23	120.00
C21—C22—C23	120.2 (3)	C19—C24—H24	119.00
C22—C23—C24	119.3 (3)	C23—C24—H24	119.00

C15—O14—C12—O13	2.1 (4)	C2—C7—C8—C12	178.8 (3)
C15—O14—C12—C8	−178.5 (3)	C7—C8—C9—C10	1.9 (4)
C12—O14—C15—C16	−86.7 (3)	C12—C8—C9—C10	−178.6 (3)
C2—N1—C10—C17	−178.4 (3)	C7—C8—C12—O13	−0.6 (5)
C2—N1—C10—C9	−0.1 (4)	C9—C8—C12—O14	0.4 (4)
C10—N1—C2—C3	−179.6 (3)	C7—C8—C12—O14	179.9 (3)
C10—N1—C2—C7	0.2 (4)	C9—C8—C12—O13	179.9 (3)
C7—C2—C3—C4	−0.8 (4)	C8—C9—C10—N1	−1.0 (4)
C3—C2—C7—C6	1.0 (4)	C8—C9—C10—C17	177.3 (3)
N1—C2—C7—C6	−178.8 (3)	N1—C10—C17—C18	7.5 (5)
N1—C2—C7—C8	0.7 (4)	C9—C10—C17—C18	−170.9 (3)
N1—C2—C3—C4	179.0 (3)	C10—C17—C18—C19	175.3 (3)
C3—C2—C7—C8	−179.5 (3)	C17—C18—C19—C20	16.4 (6)
C2—C3—C4—C5	−0.2 (4)	C17—C18—C19—C24	−161.1 (4)
C3—C4—C5—C6	1.1 (4)	C18—C19—C20—C21	−174.2 (4)
C3—C4—C5—Br11	−177.2 (2)	C24—C19—C20—C21	3.4 (5)
Br11—C5—C6—C7	177.4 (2)	C18—C19—C24—C23	174.4 (4)
C4—C5—C6—C7	−0.9 (4)	C20—C19—C24—C23	−3.3 (5)
C5—C6—C7—C2	−0.2 (4)	C19—C20—C21—C22	−1.3 (6)
C5—C6—C7—C8	−179.6 (3)	C20—C21—C22—C23	−1.1 (6)
C6—C7—C8—C9	177.8 (3)	C21—C22—C23—C24	1.2 (6)
C6—C7—C8—C12	−1.8 (4)	C22—C23—C24—C19	1.0 (6)
C2—C7—C8—C9	−1.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O13	0.93	2.22	2.848 (4)	124
C15—H15A···O13ⁱ	0.97	2.51	3.413 (4)	154

Symmetry code: (i) −x+1/2, y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O13	0.93	2.22	2.848 (4)	124
C15—H15A···O13ⁱ	0.97	2.51	3.413 (4)	154

Symmetry code: (i) −x+1/2, y+1/2, z.

Acknowledgements

The authors are grateful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, Mysuru, for providing the single-crystal X-ray diffractometer facility.

References

Beagley, P., Blackie, M. A., Chibale, K., Clarkson, C., Moss, J. R., Smith, P. & Su, H. (2003). J. Chem. Soc. Dalton Trans. pp. 3046–3051. Google Scholar
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Pradeep, P. S., Naveen, S., Kumara, M. N., Mahadevan, K. M. & Lokanath, N. K. (2014). Acta Cryst. E70, o981–o982. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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doi:10.1107/S2056989014028266

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

Crystal structure of ethyl 6-bromo-2-[(E)-2-phenyl­ethen­yl]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 6-bromo-2-[(E)-2-phenylethenyl]quinoline-4-carboxylate