Crystal structure of ethyl 6-bromo-2-[(E)-2-phenyl-ethen-yl]quinoline-4-carboxyl-ate.

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 intra-molecular C-H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds forming chains propagating along the b-axis direction.

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 ▸).

Experimental

Crystal data

C20H16BrNO2

M = 382.24

Orthorhombic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.134

S = 1.04

2722 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.92 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014028266/su5042sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

. DOI: 10.1107/S2056989014028266/su5042fig1.tif

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).

Click here for additional data file.

a . DOI: 10.1107/S2056989014028266/su5042fig2.tif

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).

CCDC reference: 1041593

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

C20H16BrNO2	F(000) = 1552
Mr = 382.24	Dx = 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

Bruker X8 Proteum diffractometer	2722 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2213 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.071
Detector resolution: 18.4 pixels mm-1	θmax = 64.5°, θmin = 5.8°
φ and ω scans	h = −16→15
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −11→11
Tmin = 0.421, Tmax = 0.476	l = −28→27
12970 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0857P)2] where P = (Fo2 + 2Fc2)/3
2722 reflections	(Δ/σ)max = 0.001
218 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.92 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
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*

	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)

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)

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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C6H6O13	0.93	2.22	2.848(4)	124
C15H15AO13i	0.97	2.51	3.413(4)	154

Symmetry code: (i) .